#------------------------------------------------------------------------------
#$Date: 2021-09-04 00:23:46 +0300 (Sat, 04 Sep 2021) $
#$Revision: 268443 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/90/4519021.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4519021
loop_
_publ_author_name
'Huke, Cameron D.'
'Taylor, Laurence J.'
'Argent, Stephen P.'
'Kays, Deborah L.'
_publ_section_title
;
 Catalyst-free Hydrophosphinylation of Isocyanates and Isothiocyanates
 under Low-Added-Solvent Conditions
;
_journal_issue                   32
_journal_name_full               'ACS Sustainable Chemistry & Engineering'
_journal_page_first              10704
_journal_page_last               10709
_journal_paper_doi               10.1021/acssuschemeng.1c02907
_journal_volume                  9
_journal_year                    2021
_chemical_formula_moiety         'C16 H18 N O2 P'
_chemical_formula_sum            'C16 H18 N O2 P'
_chemical_formula_weight         287.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-02-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                108.1640(10)
_cell_angle_beta                 109.2100(10)
_cell_angle_gamma                94.7470(10)
_cell_formula_units_Z            8
_cell_length_a                   13.2516(2)
_cell_length_b                   14.6070(2)
_cell_length_c                   17.4270(3)
_cell_measurement_reflns_used    35435
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.5440
_cell_measurement_theta_min      3.5840
_cell_volume                     2961.45(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     -7.00  19.00   1.00    3.50    --   30.00  93.00  -0.20   26
  2  ω    -12.00  13.00   1.00    3.50    --   30.00 103.00 -66.22   25
  3  ω     -1.00  24.00   1.00    3.50    --   30.00  75.00 130.61   25
  4  ω   -114.00 -23.00   1.00    3.50    --  -42.12 -38.00 120.00   91
  5  ω     20.00 109.00   1.00    3.50    --   42.12  38.00-120.00   89
  6  ω     27.00  96.00   1.00    3.50    --   42.12-125.00-180.00   69
  7  ω     29.00  96.00   1.00    3.50    --   42.12-125.00 -90.00   67
  8  ω     13.00  38.00   1.00    3.50    --   46.00  82.00-168.88   25
  9  ω     13.00  38.00   1.00    3.50    --   46.00  81.00 131.01   25
 10  ω     13.00  40.00   1.00    3.50    --   46.00  82.00  61.15   27
 11  ω     15.00  42.00   1.00    3.50    --   46.00  81.00-126.62   27
 12  ω     13.00  42.00   1.00    3.50    --   46.00  82.00 -47.24   29
 13  ω     24.00  51.00   1.00    3.50    --   54.00  74.00  23.65   27
 14  ω     65.00 127.00   1.00    3.50    --   54.00  74.00  23.65   62
 15  ω     81.00 125.00   1.00    3.50    --   58.00  72.00 -42.51   44
 16  ω     31.00  79.00   1.00    3.50    --   58.00  72.00 -42.51   48
 17  ω     27.00  54.00   1.00    3.50    --   58.00  74.00 110.41   27
 18  ω     90.00 133.00   1.00    3.50    --   62.00  74.00-124.41   43
 19  ω     33.00  60.00   1.00    3.50    --   62.00  74.00-124.41   27
 20  ω    107.00 134.00   1.00    3.50    --   66.00  73.00  45.01   27
 21  ω     37.00  64.00   1.00    3.50    --   66.00  73.00  45.01   27
 22  ω     37.00  64.00   1.00    3.50    --   66.00  73.00 -86.67   27
 23  ω    104.00 131.00   1.00    3.50    --   66.00  73.00 -86.67   27
 24  ω     35.00  61.00   1.00    3.50    --   66.00  74.00 -24.59   26
 25  ω     36.00  63.00   1.00    3.50    --   66.00  73.00 121.55   27
 26  ω     40.00  69.00   1.00    3.50    --   70.00  72.00-160.86   29
 27  ω     40.00  73.00   1.00    3.50    --   70.00  73.00 172.61   33
 28  ω     41.00  77.00   1.00    3.50    --   70.00  72.00   6.31   36
 29  ω    106.00 143.00   1.00    3.50    --   70.00  73.00 172.61   37
 30  ω     40.00  73.00   1.00    3.50    --   70.00  71.00 150.59   33
 31  ω    119.00 144.00   1.00   14.00    --   74.00  70.00-124.65   25
 32  ω     45.00  72.00   1.00   14.00    --   74.00  70.00-124.65   27
 33  ω     44.00  71.00   1.00   14.00    --   74.00  73.00  57.66   27
 34  ω     48.00  76.00   1.00   14.00    --   78.00  71.00 -89.52   28
 35  ω     53.00  79.00   1.00   14.00    --   82.00  69.00 -20.98   26
 36  ω     57.00  82.00   1.00   14.00    --   86.00  73.00  57.37   25
 37  ω     61.00  88.00   1.00   14.00    --   86.00  53.00-111.03   27
 38  ω     56.00  84.00   1.00   14.00    --   86.00  72.00 -79.56   28
 39  ω     58.00  84.00   1.00   14.00    --   86.00  65.00 179.09   26
 40  ω    114.00 158.00   1.00   14.00    --   86.00  74.00  94.65   44
 41  ω     55.00  88.00   1.00   14.00    --   86.00  74.00  94.65   33
 42  ω     62.00  89.00   1.00   14.00    --   90.00  64.00 -17.10   27
 43  ω     61.00 136.00   1.00   14.00    --   90.00  69.00  79.59   75
 44  ω     65.00  92.00   1.00   14.00    --   94.00  67.00-170.41   27
 45  ω    137.00 165.00   1.00   14.00    --   94.00  73.00 131.56   28
 46  ω     64.00  91.00   1.00   14.00    --   94.00  73.00 131.56   27
 47  ω    102.00 127.00   1.00   14.00    --  101.44 -77.00-180.00   25
 48  ω     75.00 158.00   1.00   14.00    --  101.44  61.00 120.00   83
 49  ω     27.00  86.00   1.00   14.00    --  101.44 -77.00-180.00   59
 50  ω     75.00 171.00   1.00   14.00    --  101.44  61.00 -60.00   96
 51  ω     42.00 112.00   1.00   14.00    --  101.44-125.00  90.00   70
 52  ω     76.00 151.00   1.00   14.00    --  101.44  57.00 -10.95   75
 53  ω     73.00 163.00   1.00   14.00    --  101.44  71.00  41.49   90
 54  ω     75.00 171.00   1.00   14.00    --  101.44  59.00 167.12   96
 55  ω     82.00 113.00   1.00   14.00    --  101.44-125.00 -60.00   31
 56  ω    136.00 168.00   1.00   14.00    --  101.44  61.00   0.00   32
 57  ω     76.00 103.00   1.00   14.00    --  101.44  61.00   0.00   27
 58  ω     31.00  76.00   1.00   14.00    --  101.44 -61.00  60.00   45
 59  ω     75.00 119.00   1.00   14.00    --  101.44  61.00  30.00   44
 60  ω    120.00 171.00   1.00   14.00    --  101.44  61.00-120.00   51
 61  ω     76.00 108.00   1.00   14.00    --  101.44  61.00-120.00   32
 62  ω     34.00  91.00   1.00   14.00    --  101.44 -61.00-150.00   57
 63  ω     30.00 113.00   1.00   14.00    --  101.44-125.00   0.00   83
 64  ω     28.00  53.00   1.00   14.00    --  101.44 -30.00-120.00   25
 65  ω     75.00 166.00   1.00   14.00    --  101.44  61.00-150.00   91
 66  ω     53.00  93.00   1.00   14.00    --  101.44 -61.00 -60.00   40
 67  ω     31.00 112.00   1.00   14.00    --  101.44-125.00-180.00   81
 68  ω    120.00 147.00   1.00   14.00    --  101.44  61.00 -90.00   27
 69  ω     76.00 108.00   1.00   14.00    --  101.44  61.00 -90.00   32
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0721808000
_diffrn_orient_matrix_UB_12      -0.0418513000
_diffrn_orient_matrix_UB_13      -0.0977781000
_diffrn_orient_matrix_UB_21      -0.0475770000
_diffrn_orient_matrix_UB_22      -0.0932085000
_diffrn_orient_matrix_UB_23      0.0104826000
_diffrn_orient_matrix_UB_31      -0.0914209000
_diffrn_orient_matrix_UB_32      0.0493005000
_diffrn_orient_matrix_UB_33      0.0199900000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            59544
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.525
_diffrn_reflns_theta_min         3.483
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    1.651
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_recrystallization_method 'ethanol - 30C'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     763
_refine_ls_number_reflns         11523
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0399P)²+1.0686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0779
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10732
_reflns_number_total             11523
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sc1c02907_si_002.cif
_cod_data_source_block           ochdkc
_cod_original_cell_volume        2961.44(8)
_cod_database_code               4519021
_nottingham_internal_coll_name   OCHDKC
_nottingham_internal_coll_number 18737
_nottingham_internal_coll_client CH/DLK
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '3.50, 14.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pcxch6
_nottingham_internal_coll_date   20/07/2020
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_process_date 06/08/2020
_nottingham_internal_process_user pcxch6
_nottingham_internal_solution_date 06/08/2020
_nottingham_internal_solution_user pcxch6
_nottingham_internal_refinement_date 20/08/2020
_nottingham_internal_refinement_user pcxch6
_nottingham_internal_self_archive_date 16/02/2021
_nottingham_internal_self_validation_date 16/02/2021
_nottingham_internal_self_validation_user pcxh6
_nottingham_internal_validation_date 17/02/2021
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 17/02/2021
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H18N1O2P
_chemical_oxdiff_usercomment
'OCHDKC #18737 GVA-1807 CH/DLK fomblin micromount'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.902
_shelx_estimated_absorpt_t_min   0.673
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N4-H4 = N3-H3A = N1-H1 = N2-H2A
 0.88 with sigma of 0.02
 N4-C62B \\sim N4-C62A
 with sigma of 0.02
 C63B-C62B \\sim C63A-C62A
 with sigma of 0.02
 C64B-C63B \\sim C64A-C63A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C63A, C63B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C33, C62A, C62B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C64A, C64B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C62B)=Sof(H62C)=Sof(H62D)=Sof(C63B)=Sof(H63C)=Sof(H63D)=Sof(C64B)=
 Sof(H64D)=Sof(H64E)=Sof(H64F)=1-FVAR(1)
 Sof(C62A)=Sof(H62A)=Sof(H62B)=Sof(C63A)=Sof(H63A)=Sof(H63B)=Sof(C64A)=
 Sof(H64A)=Sof(H64B)=Sof(H64C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C30(H30A,H30B), C31(H31A,H31B), C46(H46A,
 H46B), C47(H47A,H47B), C62A(H62A,H62B), C62B(H62C,H62D), C63A(H63A,H63B),
 C63B(H63C,H63D)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4A), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28), N3(H3A), C34(H34), C35(H35), C36(H36), C37(H37),
  C38(H38), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44), C50(H50),
 C51(H51), C52(H52), C53(H53), C54(H54), C56(H56), C57(H57), C58(H58), C59(H59),
  C60(H60)
5.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C32(H32A,H32B,H32C), C48(H48A,H48B,H48C), C64A(H64A,H64B,
 H64C), C64B(H64D,H64E,H64F)
;
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id OCHDKC
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.765
_oxdiff_exptl_absorpt_empirical_full_min 0.719
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.07112(2) 0.71734(2) -0.03402(2) 0.01636(7) Uani 1 1 d . . . . .
O1 O 0.15815(6) 0.68211(6) 0.02167(5) 0.02215(17) Uani 1 1 d . . . . .
O2 O 0.05681(6) 0.80414(6) -0.15221(5) 0.02327(18) Uani 1 1 d . . . . .
N1 N 0.22952(8) 0.81853(7) -0.05855(6) 0.0206(2) Uani 1 1 d D . . . .
H1 H 0.2716(11) 0.8054(10) -0.0147(9) 0.025 Uiso 1 1 d D U . . .
C1 C 0.01281(8) 0.80456(8) 0.02821(7) 0.0166(2) Uani 1 1 d . . . . .
C2 C 0.03539(9) 0.81092(8) 0.11412(7) 0.0200(2) Uani 1 1 d . . . . .
H2 H 0.079448 0.770281 0.136887 0.024 Uiso 1 1 calc R U . . .
C3 C -0.00635(10) 0.87638(9) 0.16611(7) 0.0234(2) Uani 1 1 d . . . . .
H3 H 0.008871 0.880266 0.224377 0.028 Uiso 1 1 calc R U . . .
C4 C -0.07027(10) 0.93626(9) 0.13341(8) 0.0236(2) Uani 1 1 d . . . . .
H4A H -0.099282 0.980673 0.169099 0.028 Uiso 1 1 calc R U . . .
C5 C -0.09188(9) 0.93126(9) 0.04838(8) 0.0221(2) Uani 1 1 d . . . . .
H5 H -0.134939 0.972884 0.026274 0.027 Uiso 1 1 calc R U . . .
C6 C -0.05073(9) 0.86565(8) -0.00430(7) 0.0193(2) Uani 1 1 d . . . . .
H6 H -0.065760 0.862275 -0.062422 0.023 Uiso 1 1 calc R U . . .
C7 C -0.03633(9) 0.61847(8) -0.11910(7) 0.0187(2) Uani 1 1 d . . . . .
C8 C -0.02173(10) 0.52274(9) -0.12816(8) 0.0226(2) Uani 1 1 d . . . . .
H8 H 0.040936 0.511891 -0.088641 0.027 Uiso 1 1 calc R U . . .
C9 C -0.09910(10) 0.44323(9) -0.19514(9) 0.0272(3) Uani 1 1 d . . . . .
H9 H -0.089100 0.377991 -0.201551 0.033 Uiso 1 1 calc R U . . .
C10 C -0.19048(10) 0.45893(9) -0.25241(8) 0.0272(3) Uani 1 1 d . . . . .
H10 H -0.242529 0.404384 -0.298612 0.033 Uiso 1 1 calc R U . . .
C11 C -0.20680(10) 0.55400(9) -0.24290(8) 0.0264(3) Uani 1 1 d . . . . .
H11 H -0.270448 0.564311 -0.281837 0.032 Uiso 1 1 calc R U . . .
C12 C -0.12984(10) 0.63382(9) -0.17635(8) 0.0233(2) Uani 1 1 d . . . . .
H12 H -0.140725 0.698877 -0.169714 0.028 Uiso 1 1 calc R U . . .
C13 C 0.12183(9) 0.78752(8) -0.09140(7) 0.0178(2) Uani 1 1 d . . . . .
C14 C 0.28398(10) 0.87640(9) -0.09408(8) 0.0233(2) Uani 1 1 d . . . . .
H14A H 0.354161 0.916726 -0.047965 0.028 Uiso 1 1 calc R U . . .
H14B H 0.237875 0.921878 -0.111722 0.028 Uiso 1 1 calc R U . . .
C15 C 0.30582(11) 0.81302(10) -0.17183(9) 0.0291(3) Uani 1 1 d . . . . .
H15A H 0.236450 0.769785 -0.216881 0.035 Uiso 1 1 calc R U . . .
H15B H 0.356058 0.770587 -0.153625 0.035 Uiso 1 1 calc R U . . .
C16 C 0.35604(14) 0.87615(12) -0.21018(11) 0.0437(4) Uani 1 1 d . . . . .
H16A H 0.368500 0.833491 -0.260663 0.066 Uiso 1 1 calc R U . . .
H16B H 0.425738 0.917633 -0.166126 0.066 Uiso 1 1 calc R U . . .
H16C H 0.306217 0.917984 -0.228452 0.066 Uiso 1 1 calc R U . . .
P2 P 0.49755(2) 0.77195(2) 0.09640(2) 0.01535(7) Uani 1 1 d . . . . .
O3 O 0.40313(6) 0.82252(6) 0.08630(5) 0.02062(17) Uani 1 1 d . . . . .
O4 O 0.53254(6) 0.60066(6) 0.11876(5) 0.02081(17) Uani 1 1 d . . . . .
N2 N 0.35733(8) 0.62584(7) 0.08916(6) 0.01868(19) Uani 1 1 d D . . . .
H2A H 0.3157(11) 0.6656(10) 0.0781(9) 0.022 Uiso 1 1 d D U . . .
C17 C 0.61233(9) 0.84169(8) 0.19465(7) 0.0166(2) Uani 1 1 d . . . . .
C18 C 0.58939(9) 0.90972(8) 0.25970(7) 0.0198(2) Uani 1 1 d . . . . .
H18 H 0.515878 0.914910 0.251514 0.024 Uiso 1 1 calc R U . . .
C19 C 0.67341(10) 0.96998(8) 0.33643(8) 0.0238(2) Uani 1 1 d . . . . .
H19 H 0.657747 1.016955 0.380452 0.029 Uiso 1 1 calc R U . . .
C20 C 0.78029(10) 0.96109(9) 0.34833(8) 0.0238(2) Uani 1 1 d . . . . .
H20 H 0.838081 1.002775 0.400453 0.029 Uiso 1 1 calc R U . . .
C21 C 0.80361(10) 0.89179(9) 0.28474(8) 0.0254(3) Uani 1 1 d . . . . .
H21 H 0.876992 0.885217 0.294043 0.030 Uiso 1 1 calc R U . . .
C22 C 0.71988(9) 0.83204(9) 0.20756(8) 0.0226(2) Uani 1 1 d . . . . .
H22 H 0.735783 0.784870 0.163809 0.027 Uiso 1 1 calc R U . . .
C23 C 0.53967(9) 0.74568(8) 0.00505(7) 0.0196(2) Uani 1 1 d . . . . .
C24 C 0.59793(10) 0.82251(10) -0.00501(8) 0.0288(3) Uani 1 1 d . . . . .
H24 H 0.624166 0.885425 0.040262 0.035 Uiso 1 1 calc R U . . .
C25 C 0.61743(12) 0.80681(12) -0.08120(9) 0.0375(3) Uani 1 1 d . . . . .
H25 H 0.657609 0.858906 -0.087742 0.045 Uiso 1 1 calc R U . . .
C26 C 0.57850(11) 0.71541(12) -0.14773(9) 0.0369(3) Uani 1 1 d . . . . .
H26 H 0.591369 0.705116 -0.199998 0.044 Uiso 1 1 calc R U . . .
C27 C 0.52091(11) 0.63918(10) -0.13803(8) 0.0306(3) Uani 1 1 d . . . . .
H27 H 0.494281 0.576619 -0.183779 0.037 Uiso 1 1 calc R U . . .
C28 C 0.50173(10) 0.65353(9) -0.06180(7) 0.0231(2) Uani 1 1 d . . . . .
H28 H 0.462865 0.600693 -0.055214 0.028 Uiso 1 1 calc R U . . .
C29 C 0.46233(9) 0.64991(8) 0.10334(7) 0.0163(2) Uani 1 1 d . . . . .
C30 C 0.30385(9) 0.52819(8) 0.07715(8) 0.0210(2) Uani 1 1 d . . . . .
H30A H 0.239734 0.533422 0.094273 0.025 Uiso 1 1 calc R U . . .
H30B H 0.355135 0.500377 0.115013 0.025 Uiso 1 1 calc R U . . .
C31 C 0.26727(9) 0.46017(8) -0.01741(8) 0.0221(2) Uani 1 1 d . . . . .
H31A H 0.332379 0.445225 -0.030906 0.027 Uiso 1 1 calc R U . . .
H31B H 0.228412 0.494259 -0.055616 0.027 Uiso 1 1 calc R U . . .
C32 C 0.19249(11) 0.36425(10) -0.03679(10) 0.0346(3) Uani 1 1 d . . . . .
H32A H 0.166182 0.325173 -0.099184 0.052 Uiso 1 1 calc R U . . .
H32B H 0.130132 0.378779 -0.020145 0.052 Uiso 1 1 calc R U . . .
H32C H 0.232988 0.327004 -0.003515 0.052 Uiso 1 1 calc R U . . .
P3 P 0.08503(2) 0.71717(2) 0.44357(2) 0.01733(7) Uani 1 1 d . . . . .
O5 O 0.17520(6) 0.67618(6) 0.48901(5) 0.02415(18) Uani 1 1 d . . . . .
O6 O 0.06178(7) 0.83047(7) 0.34565(6) 0.02823(19) Uani 1 1 d . . . . .
N3 N 0.23788(8) 0.84005(7) 0.43215(6) 0.0211(2) Uani 1 1 d D . . . .
H3A H 0.279411 0.814698 0.467605 0.025 Uiso 1 1 calc DR U . . .
C33 C -0.02426(9) 0.62306(8) 0.35531(7) 0.0195(2) Uani 1 1 d . . . . .
C34 C -0.01185(10) 0.52588(9) 0.34069(8) 0.0240(2) Uani 1 1 d . . . . .
H34 H 0.052864 0.512299 0.375418 0.029 Uiso 1 1 calc R U . . .
C35 C -0.09418(11) 0.44900(9) 0.27533(8) 0.0290(3) Uani 1 1 d . . . . .
H35 H -0.085631 0.382856 0.265227 0.035 Uiso 1 1 calc R U . . .
C36 C -0.18870(11) 0.46877(10) 0.22491(8) 0.0294(3) Uani 1 1 d . . . . .
H36 H -0.244738 0.416031 0.180179 0.035 Uiso 1 1 calc R U . . .
C37 C -0.20204(10) 0.56506(10) 0.23930(8) 0.0275(3) Uani 1 1 d . . . . .
H37 H -0.267182 0.578150 0.204660 0.033 Uiso 1 1 calc R U . . .
C38 C -0.12011(10) 0.64231(9) 0.30438(8) 0.0236(2) Uani 1 1 d . . . . .
H38 H -0.129203 0.708296 0.314293 0.028 Uiso 1 1 calc R U . . .
C39 C 0.02700(9) 0.79068(8) 0.51566(7) 0.0193(2) Uani 1 1 d . . . . .
C40 C 0.04917(11) 0.77958(10) 0.59585(8) 0.0308(3) Uani 1 1 d . . . . .
H40 H 0.093053 0.734679 0.610400 0.037 Uiso 1 1 calc R U . . .
C41 C 0.00719(13) 0.83407(11) 0.65439(9) 0.0374(3) Uani 1 1 d . . . . .
H41 H 0.021904 0.826065 0.708810 0.045 Uiso 1 1 calc R U . . .
C42 C -0.05612(11) 0.90010(10) 0.63364(8) 0.0299(3) Uani 1 1 d . . . . .
H42 H -0.084814 0.937259 0.673844 0.036 Uiso 1 1 calc R U . . .
C43 C -0.07773(10) 0.91213(9) 0.55442(8) 0.0251(2) Uani 1 1 d . . . . .
H43 H -0.120715 0.957893 0.540597 0.030 Uiso 1 1 calc R U . . .
C44 C -0.03669(9) 0.85741(9) 0.49520(7) 0.0214(2) Uani 1 1 d . . . . .
H44 H -0.051990 0.865433 0.440726 0.026 Uiso 1 1 calc R U . . .
C45 C 0.13046(9) 0.80542(8) 0.39838(7) 0.0194(2) Uani 1 1 d . . . . .
C46 C 0.29071(10) 0.91829(9) 0.41335(8) 0.0263(3) Uani 1 1 d . . . . .
H46A H 0.326143 0.976445 0.467763 0.032 Uiso 1 1 calc R U . . .
H46B H 0.234368 0.938128 0.371618 0.032 Uiso 1 1 calc R U . . .
C47 C 0.37567(10) 0.88610(10) 0.37550(9) 0.0285(3) Uani 1 1 d . . . . .
H47A H 0.417762 0.944364 0.374057 0.034 Uiso 1 1 calc R U . . .
H47B H 0.427223 0.859302 0.414181 0.034 Uiso 1 1 calc R U . . .
C48 C 0.32649(15) 0.80907(11) 0.28459(11) 0.0445(4) Uani 1 1 d . . . . .
H48A H 0.283127 0.837922 0.244274 0.067 Uiso 1 1 calc R U . . .
H48B H 0.279426 0.753558 0.284433 0.067 Uiso 1 1 calc R U . . .
H48C H 0.385068 0.785842 0.266167 0.067 Uiso 1 1 calc R U . . .
P4 P 0.50191(2) 0.76630(2) 0.58331(2) 0.01637(7) Uani 1 1 d . . . . .
O7 O 0.41163(6) 0.82124(6) 0.56844(5) 0.02147(17) Uani 1 1 d . . . . .
O8 O 0.53804(7) 0.61170(6) 0.63272(6) 0.02483(18) Uani 1 1 d . . . . .
N4 N 0.36130(8) 0.63342(8) 0.59589(7) 0.0233(2) Uani 1 1 d D . . . .
H4 H 0.3172(11) 0.6665(10) 0.5744(10) 0.028 Uiso 1 1 d D U . . .
C49 C 0.62024(9) 0.83796(8) 0.67802(7) 0.0172(2) Uani 1 1 d . . . . .
C50 C 0.60665(9) 0.92347(8) 0.73399(7) 0.0202(2) Uani 1 1 d . . . . .
H50 H 0.537433 0.941496 0.720525 0.024 Uiso 1 1 calc R U . . .
C51 C 0.69350(10) 0.98270(8) 0.80939(8) 0.0225(2) Uani 1 1 d . . . . .
H51 H 0.683999 1.041030 0.847479 0.027 Uiso 1 1 calc R U . . .
C52 C 0.79423(10) 0.95571(8) 0.82845(7) 0.0216(2) Uani 1 1 d . . . . .
H52 H 0.854129 0.996242 0.879581 0.026 Uiso 1 1 calc R U . . .
C53 C 0.80835(9) 0.86982(9) 0.77336(8) 0.0214(2) Uani 1 1 d . . . . .
H53 H 0.877593 0.851864 0.787217 0.026 Uiso 1 1 calc R U . . .
C54 C 0.72159(9) 0.81035(8) 0.69826(7) 0.0202(2) Uani 1 1 d . . . . .
H54 H 0.730924 0.751370 0.660890 0.024 Uiso 1 1 calc R U . . .
C55 C 0.54197(9) 0.72390(8) 0.49134(7) 0.0184(2) Uani 1 1 d . . . . .
C56 C 0.62550(10) 0.78052(9) 0.48367(8) 0.0252(2) Uani 1 1 d . . . . .
H56 H 0.669933 0.837923 0.531382 0.030 Uiso 1 1 calc R U . . .
C57 C 0.64392(11) 0.75320(10) 0.40640(9) 0.0299(3) Uani 1 1 d . . . . .
H57 H 0.701353 0.791598 0.401538 0.036 Uiso 1 1 calc R U . . .
C58 C 0.57861(11) 0.66998(10) 0.33637(8) 0.0284(3) Uani 1 1 d . . . . .
H58 H 0.590289 0.652063 0.283146 0.034 Uiso 1 1 calc R U . . .
C59 C 0.49645(11) 0.61312(10) 0.34414(8) 0.0298(3) Uani 1 1 d . . . . .
H59 H 0.452231 0.555755 0.296277 0.036 Uiso 1 1 calc R U . . .
C60 C 0.47811(10) 0.63921(9) 0.42128(8) 0.0251(2) Uani 1 1 d . . . . .
H60 H 0.422049 0.599376 0.426379 0.030 Uiso 1 1 calc R U . . .
C61 C 0.46560(9) 0.65460(8) 0.60635(7) 0.0185(2) Uani 1 1 d . . . . .
C62A C 0.31892(18) 0.55486(17) 0.62120(16) 0.0273(5) Uani 0.838(4) 1 d D . P A
1
H62A H 0.300942 0.585473 0.673033 0.033 Uiso 0.838(4) 1 calc R U P A 1
H62B H 0.376674 0.517807 0.637424 0.033 Uiso 0.838(4) 1 calc R U P A 1
C62B C 0.3023(9) 0.5411(7) 0.5832(7) 0.026(3) Uani 0.162(4) 1 d D . P A 2
H62C H 0.238402 0.552196 0.599631 0.031 Uiso 0.162(4) 1 calc R U P A 2
H62D H 0.349542 0.513391 0.623570 0.031 Uiso 0.162(4) 1 calc R U P A 2
C63A C 0.21748(12) 0.48337(11) 0.54829(10) 0.0285(4) Uani 0.838(4) 1 d D . P A
1
H63A H 0.193446 0.432245 0.568437 0.034 Uiso 0.838(4) 1 calc R U P A 1
H63B H 0.157896 0.519576 0.535419 0.034 Uiso 0.838(4) 1 calc R U P A 1
C63B C 0.2625(11) 0.4657(9) 0.4929(9) 0.030(3) Uani 0.162(4) 1 d D . P A 2
H63C H 0.324665 0.439285 0.481353 0.036 Uiso 0.162(4) 1 calc R U P A 2
H63D H 0.230699 0.496914 0.449977 0.036 Uiso 0.162(4) 1 calc R U P A 2
C64A C 0.2367(3) 0.4340(2) 0.46574(19) 0.0389(7) Uani 0.838(4) 1 d D . P A 1
H64A H 0.170988 0.385248 0.422862 0.058 Uiso 0.838(4) 1 calc R U P A 1
H64B H 0.298302 0.401015 0.478633 0.058 Uiso 0.838(4) 1 calc R U P A 1
H64C H 0.253233 0.483529 0.442136 0.058 Uiso 0.838(4) 1 calc R U P A 1
C64B C 0.1775(7) 0.3829(7) 0.4827(8) 0.046(3) Uani 0.162(4) 1 d D . P A 2
H64D H 0.209165 0.352252 0.525294 0.069 Uiso 0.162(4) 1 calc R U P A 2
H64E H 0.152881 0.333629 0.423720 0.069 Uiso 0.162(4) 1 calc R U P A 2
H64F H 0.115205 0.408988 0.492535 0.069 Uiso 0.162(4) 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 3 0 0.0579
2 -1 -5 0.0787
2 -2 -5 0.0725
-4 1 -5 0.0727
3 -3 -5 0.0640
2 -3 -5 0.0661
5 1 -1 0.0939
0 -5 -2 0.0418
1 -5 -1 0.0305
-1 5 1 0.0414
-2 -5 0 0.0361
2 5 0 0.0541
-2 -5 1 0.0279
2 5 -1 0.0541
0 1 0 0.0330
-1 -5 1 0.0306
-2 -5 3 0.0395
4 -5 -1 0.0719
-3 1 5 0.0779
5 -3 -1 0.0913
4 -3 5 0.1406
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C1 112.49(5) . . ?
O1 P1 C7 112.94(5) . . ?
O1 P1 C13 113.36(5) . . ?
C1 P1 C13 102.85(5) . . ?
C7 P1 C1 109.45(5) . . ?
C7 P1 C13 105.04(5) . . ?
C13 N1 H1 121.8(9) . . ?
C13 N1 C14 121.79(10) . . ?
C14 N1 H1 116.4(9) . . ?
C2 C1 P1 116.73(8) . . ?
C6 C1 P1 123.73(8) . . ?
C6 C1 C2 119.53(10) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.11(10) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.24(11) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4A 120.0 . . ?
C3 C4 C5 119.96(11) . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.20(11) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.94(10) . . ?
C5 C6 H6 120.0 . . ?
C8 C7 P1 116.97(9) . . ?
C8 C7 C12 119.76(10) . . ?
C12 C7 P1 123.25(9) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.85(11) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.11(11) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.46(11) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.80(11) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.00(11) . . ?
C11 C12 H12 120.0 . . ?
O2 C13 P1 120.19(8) . . ?
O2 C13 N1 125.77(10) . . ?
N1 C13 P1 114.00(8) . . ?
N1 C14 H14A 109.0 . . ?
N1 C14 H14B 109.0 . . ?
N1 C14 C15 112.82(10) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C14 C15 C16 111.11(11) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 P2 C17 111.54(5) . . ?
O3 P2 C23 113.09(5) . . ?
O3 P2 C29 111.43(5) . . ?
C17 P2 C23 109.43(5) . . ?
C17 P2 C29 106.37(5) . . ?
C23 P2 C29 104.55(5) . . ?
C29 N2 H2A 119.1(9) . . ?
C29 N2 C30 123.50(10) . . ?
C30 N2 H2A 116.6(9) . . ?
C18 C17 P2 116.22(8) . . ?
C18 C17 C22 119.91(10) . . ?
C22 C17 P2 123.86(9) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.32(11) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.49(11) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.54(11) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.12(11) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 H22 120.2 . . ?
C21 C22 C17 119.59(11) . . ?
C21 C22 H22 120.2 . . ?
C24 C23 P2 119.16(9) . . ?
C28 C23 P2 120.68(9) . . ?
C28 C23 C24 119.51(11) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 119.97(12) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.23(13) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.00(12) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 119.8 . . ?
C26 C27 C28 120.41(13) . . ?
C28 C27 H27 119.8 . . ?
C23 C28 H28 120.1 . . ?
C27 C28 C23 119.88(12) . . ?
C27 C28 H28 120.1 . . ?
O4 C29 P2 120.75(8) . . ?
O4 C29 N2 127.27(10) . . ?
N2 C29 P2 111.97(8) . . ?
N2 C30 H30A 109.6 . . ?
N2 C30 H30B 109.6 . . ?
N2 C30 C31 110.45(9) . . ?
H30A C30 H30B 108.1 . . ?
C31 C30 H30A 109.6 . . ?
C31 C30 H30B 109.6 . . ?
C30 C31 H31A 109.2 . . ?
C30 C31 H31B 109.2 . . ?
C30 C31 C32 112.25(10) . . ?
H31A C31 H31B 107.9 . . ?
C32 C31 H31A 109.2 . . ?
C32 C31 H31B 109.2 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O5 P3 C33 112.60(5) . . ?
O5 P3 C39 112.74(5) . . ?
O5 P3 C45 113.15(5) . . ?
C33 P3 C39 107.77(5) . . ?
C33 P3 C45 107.36(5) . . ?
C39 P3 C45 102.55(5) . . ?
C45 N3 H3A 118.3 . . ?
C45 N3 C46 123.46(10) . . ?
C46 N3 H3A 118.3 . . ?
C34 C33 P3 116.62(9) . . ?
C34 C33 C38 119.62(11) . . ?
C38 C33 P3 123.72(9) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 C33 119.97(11) . . ?
C35 C34 H34 120.0 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 120.02(12) . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 119.8 . . ?
C35 C36 C37 120.41(12) . . ?
C37 C36 H36 119.8 . . ?
C36 C37 H37 120.0 . . ?
C36 C37 C38 119.93(12) . . ?
C38 C37 H37 120.0 . . ?
C33 C38 H38 120.0 . . ?
C37 C38 C33 120.04(11) . . ?
C37 C38 H38 120.0 . . ?
C40 C39 P3 117.13(9) . . ?
C40 C39 C44 119.57(11) . . ?
C44 C39 P3 123.30(9) . . ?
C39 C40 H40 120.0 . . ?
C41 C40 C39 120.04(12) . . ?
C41 C40 H40 120.0 . . ?
C40 C41 H41 119.9 . . ?
C42 C41 C40 120.12(12) . . ?
C42 C41 H41 119.9 . . ?
C41 C42 H42 119.9 . . ?
C41 C42 C43 120.17(12) . . ?
C43 C42 H42 119.9 . . ?
C42 C43 H43 119.9 . . ?
C42 C43 C44 120.10(12) . . ?
C44 C43 H43 119.9 . . ?
C39 C44 H44 120.0 . . ?
C43 C44 C39 119.99(11) . . ?
C43 C44 H44 120.0 . . ?
O6 C45 P3 119.55(9) . . ?
O6 C45 N3 126.30(11) . . ?
N3 C45 P3 114.02(8) . . ?
N3 C46 H46A 109.1 . . ?
N3 C46 H46B 109.1 . . ?
N3 C46 C47 112.35(10) . . ?
H46A C46 H46B 107.9 . . ?
C47 C46 H46A 109.1 . . ?
C47 C46 H46B 109.1 . . ?
C46 C47 H47A 109.0 . . ?
C46 C47 H47B 109.0 . . ?
H47A C47 H47B 107.8 . . ?
C48 C47 C46 113.11(11) . . ?
C48 C47 H47A 109.0 . . ?
C48 C47 H47B 109.0 . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
O7 P4 C49 112.12(5) . . ?
O7 P4 C55 113.00(5) . . ?
O7 P4 C61 112.96(5) . . ?
C49 P4 C55 108.91(5) . . ?
C49 P4 C61 103.56(5) . . ?
C55 P4 C61 105.67(5) . . ?
C61 N4 H4 119.1(10) . . ?
C61 N4 C62A 122.17(13) . . ?
C61 N4 C62B 126.4(5) . . ?
C62A N4 H4 118.7(10) . . ?
C62B N4 H4 109.7(11) . . ?
C50 C49 P4 116.66(8) . . ?
C50 C49 C54 119.92(10) . . ?
C54 C49 P4 123.39(9) . . ?
C49 C50 H50 119.7 . . ?
C51 C50 C49 120.54(11) . . ?
C51 C50 H50 119.7 . . ?
C50 C51 H51 120.4 . . ?
C52 C51 C50 119.27(11) . . ?
C52 C51 H51 120.4 . . ?
C51 C52 H52 119.7 . . ?
C51 C52 C53 120.62(11) . . ?
C53 C52 H52 119.7 . . ?
C52 C53 H53 119.9 . . ?
C54 C53 C52 120.18(11) . . ?
C54 C53 H53 119.9 . . ?
C49 C54 H54 120.3 . . ?
C53 C54 C49 119.46(10) . . ?
C53 C54 H54 120.3 . . ?
C56 C55 P4 121.39(9) . . ?
C56 C55 C60 119.45(11) . . ?
C60 C55 P4 118.57(9) . . ?
C55 C56 H56 119.9 . . ?
C57 C56 C55 120.13(11) . . ?
C57 C56 H56 119.9 . . ?
C56 C57 H57 119.9 . . ?
C58 C57 C56 120.10(12) . . ?
C58 C57 H57 119.9 . . ?
C57 C58 H58 120.1 . . ?
C59 C58 C57 119.86(12) . . ?
C59 C58 H58 120.1 . . ?
C58 C59 H59 119.8 . . ?
C58 C59 C60 120.48(12) . . ?
C60 C59 H59 119.8 . . ?
C55 C60 H60 120.0 . . ?
C59 C60 C55 119.96(11) . . ?
C59 C60 H60 120.0 . . ?
O8 C61 P4 118.95(9) . . ?
O8 C61 N4 127.17(11) . . ?
N4 C61 P4 113.79(8) . . ?
N4 C62A H62A 109.1 . . ?
N4 C62A H62B 109.1 . . ?
N4 C62A C63A 112.50(16) . . ?
H62A C62A H62B 107.8 . . ?
C63A C62A H62A 109.1 . . ?
C63A C62A H62B 109.1 . . ?
N4 C62B H62C 108.3 . . ?
N4 C62B H62D 108.3 . . ?
N4 C62B C63B 116.1(10) . . ?
H62C C62B H62D 107.4 . . ?
C63B C62B H62C 108.3 . . ?
C63B C62B H62D 108.3 . . ?
C62A C63A H63A 109.0 . . ?
C62A C63A H63B 109.0 . . ?
H63A C63A H63B 107.8 . . ?
C64A C63A C62A 112.92(17) . . ?
C64A C63A H63A 109.0 . . ?
C64A C63A H63B 109.0 . . ?
C62B C63B H63C 109.6 . . ?
C62B C63B H63D 109.6 . . ?
C62B C63B C64B 110.2(12) . . ?
H63C C63B H63D 108.1 . . ?
C64B C63B H63C 109.6 . . ?
C64B C63B H63D 109.6 . . ?
C63A C64A H64A 109.5 . . ?
C63A C64A H64B 109.5 . . ?
C63A C64A H64C 109.5 . . ?
H64A C64A H64B 109.5 . . ?
H64A C64A H64C 109.5 . . ?
H64B C64A H64C 109.5 . . ?
C63B C64B H64D 109.5 . . ?
C63B C64B H64E 109.5 . . ?
C63B C64B H64F 109.5 . . ?
H64D C64B H64E 109.5 . . ?
H64D C64B H64F 109.5 . . ?
H64E C64B H64F 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4867(8) . ?
P1 C1 1.8025(11) . ?
P1 C7 1.8019(11) . ?
P1 C13 1.8626(11) . ?
O2 C13 1.2323(13) . ?
N1 H1 0.872(12) . ?
N1 C13 1.3279(15) . ?
N1 C14 1.4622(14) . ?
C1 C2 1.3976(15) . ?
C1 C6 1.3971(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.3850(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.3867(17) . ?
C4 H4A 0.9500 . ?
C4 C5 1.3904(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3878(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3945(16) . ?
C7 C12 1.3975(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.3902(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3815(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3902(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.3879(17) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5156(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5215(18) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
P2 O3 1.4938(8) . ?
P2 C17 1.7959(11) . ?
P2 C23 1.7978(12) . ?
P2 C29 1.8558(11) . ?
O4 C29 1.2338(13) . ?
N2 H2A 0.856(12) . ?
N2 C29 1.3264(14) . ?
N2 C30 1.4592(14) . ?
C17 C18 1.3927(16) . ?
C17 C22 1.3942(16) . ?
C18 H18 0.9500 . ?
C18 C19 1.3881(16) . ?
C19 H19 0.9500 . ?
C19 C20 1.3856(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.3879(18) . ?
C21 H21 0.9500 . ?
C21 C22 1.3884(17) . ?
C22 H22 0.9500 . ?
C23 C24 1.3980(17) . ?
C23 C28 1.3953(16) . ?
C24 H24 0.9500 . ?
C24 C25 1.3887(19) . ?
C25 H25 0.9500 . ?
C25 C26 1.386(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.383(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.3895(17) . ?
C28 H28 0.9500 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.5204(16) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.5212(16) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
P3 O5 1.4847(8) . ?
P3 C33 1.7999(11) . ?
P3 C39 1.8039(12) . ?
P3 C45 1.8605(11) . ?
O6 C45 1.2332(14) . ?
N3 H3A 0.8800 . ?
N3 C45 1.3313(15) . ?
N3 C46 1.4682(14) . ?
C33 C34 1.3956(17) . ?
C33 C38 1.3974(16) . ?
C34 H34 0.9500 . ?
C34 C35 1.3895(17) . ?
C35 H35 0.9500 . ?
C35 C36 1.3850(19) . ?
C36 H36 0.9500 . ?
C36 C37 1.3867(19) . ?
C37 H37 0.9500 . ?
C37 C38 1.3883(17) . ?
C38 H38 0.9500 . ?
C39 C40 1.3943(16) . ?
C39 C44 1.3945(16) . ?
C40 H40 0.9500 . ?
C40 C41 1.3872(19) . ?
C41 H41 0.9500 . ?
C41 C42 1.384(2) . ?
C42 H42 0.9500 . ?
C42 C43 1.3849(18) . ?
C43 H43 0.9500 . ?
C43 C44 1.3881(17) . ?
C44 H44 0.9500 . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C46 C47 1.5188(18) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C47 C48 1.513(2) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
P4 O7 1.4923(8) . ?
P4 C49 1.7963(11) . ?
P4 C55 1.7973(12) . ?
P4 C61 1.8601(11) . ?
O8 C61 1.2305(14) . ?
N4 H4 0.854(12) . ?
N4 C61 1.3296(15) . ?
N4 C62A 1.483(2) . ?
N4 C62B 1.416(11) . ?
C49 C50 1.3919(16) . ?
C49 C54 1.3990(15) . ?
C50 H50 0.9500 . ?
C50 C51 1.3897(16) . ?
C51 H51 0.9500 . ?
C51 C52 1.3872(17) . ?
C52 H52 0.9500 . ?
C52 C53 1.3917(17) . ?
C53 H53 0.9500 . ?
C53 C54 1.3875(16) . ?
C54 H54 0.9500 . ?
C55 C56 1.3935(16) . ?
C55 C60 1.3936(16) . ?
C56 H56 0.9500 . ?
C56 C57 1.3890(18) . ?
C57 H57 0.9500 . ?
C57 C58 1.3864(19) . ?
C58 H58 0.9500 . ?
C58 C59 1.3824(19) . ?
C59 H59 0.9500 . ?
C59 C60 1.3865(18) . ?
C60 H60 0.9500 . ?
C62A H62A 0.9900 . ?
C62A H62B 0.9900 . ?
C62A C63A 1.526(3) . ?
C62B H62C 0.9900 . ?
C62B H62D 0.9900 . ?
C62B C63B 1.498(14) . ?
C63A H63A 0.9900 . ?
C63A H63B 0.9900 . ?
C63A C64A 1.510(3) . ?
C63B H63C 0.9900 . ?
C63B H63D 0.9900 . ?
C63B C64B 1.509(12) . ?
C64A H64A 0.9800 . ?
C64A H64B 0.9800 . ?
C64A H64C 0.9800 . ?
C64B H64D 0.9800 . ?
C64B H64E 0.9800 . ?
C64B H64F 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.872(12) 1.957(13) 2.7808(12) 156.9(13) . yes
N2 H2A O1 0.856(12) 2.064(13) 2.8186(12) 146.6(13) . yes
N3 H3A O7 0.88 2.00 2.8161(12) 153.3 . yes
N4 H4 O5 0.854(12) 2.027(13) 2.8105(13) 152.0(14) . yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 C3 179.87(9) . . . . ?
P1 C1 C6 C5 -179.56(9) . . . . ?
P1 C7 C8 C9 -176.93(9) . . . . ?
P1 C7 C12 C11 176.98(9) . . . . ?
O1 P1 C1 C2 -14.50(10) . . . . ?
O1 P1 C1 C6 164.40(9) . . . . ?
O1 P1 C7 C8 -5.57(11) . . . . ?
O1 P1 C7 C12 176.23(9) . . . . ?
O1 P1 C13 O2 165.60(9) . . . . ?
O1 P1 C13 N1 -16.67(10) . . . . ?
N1 C14 C15 C16 176.48(11) . . . . ?
C1 P1 C7 C8 -131.72(9) . . . . ?
C1 P1 C7 C12 50.08(11) . . . . ?
C1 P1 C13 O2 -72.68(10) . . . . ?
C1 P1 C13 N1 105.06(9) . . . . ?
C1 C2 C3 C4 -0.32(17) . . . . ?
C2 C1 C6 C5 -0.70(16) . . . . ?
C2 C3 C4 C5 -0.54(18) . . . . ?
C3 C4 C5 C6 0.77(18) . . . . ?
C4 C5 C6 C1 -0.14(17) . . . . ?
C6 C1 C2 C3 0.93(16) . . . . ?
C7 P1 C1 C2 111.92(9) . . . . ?
C7 P1 C1 C6 -69.19(10) . . . . ?
C7 P1 C13 O2 41.84(10) . . . . ?
C7 P1 C13 N1 -140.43(9) . . . . ?
C7 C8 C9 C10 -0.28(18) . . . . ?
C8 C7 C12 C11 -1.17(18) . . . . ?
C8 C9 C10 C11 -0.97(19) . . . . ?
C9 C10 C11 C12 1.14(19) . . . . ?
C10 C11 C12 C7 -0.06(18) . . . . ?
C12 C7 C8 C9 1.34(17) . . . . ?
C13 P1 C1 C2 -136.81(8) . . . . ?
C13 P1 C1 C6 42.08(10) . . . . ?
C13 P1 C7 C8 118.46(9) . . . . ?
C13 P1 C7 C12 -59.75(11) . . . . ?
C13 N1 C14 C15 -84.30(14) . . . . ?
C14 N1 C13 P1 -178.86(8) . . . . ?
C14 N1 C13 O2 -1.28(18) . . . . ?
P2 C17 C18 C19 -177.21(9) . . . . ?
P2 C17 C22 C21 177.76(9) . . . . ?
P2 C23 C24 C25 -170.69(10) . . . . ?
P2 C23 C28 C27 169.89(9) . . . . ?
O3 P2 C17 C18 21.38(10) . . . . ?
O3 P2 C17 C22 -157.59(9) . . . . ?
O3 P2 C23 C24 74.93(10) . . . . ?
O3 P2 C23 C28 -95.78(10) . . . . ?
O3 P2 C29 O4 -174.19(8) . . . . ?
O3 P2 C29 N2 6.45(9) . . . . ?
N2 C30 C31 C32 -169.05(10) . . . . ?
C17 P2 C23 C24 -50.07(11) . . . . ?
C17 P2 C23 C28 139.22(9) . . . . ?
C17 P2 C29 O4 -52.43(10) . . . . ?
C17 P2 C29 N2 128.21(8) . . . . ?
C17 C18 C19 C20 -0.82(17) . . . . ?
C18 C17 C22 C21 -1.18(17) . . . . ?
C18 C19 C20 C21 -0.80(18) . . . . ?
C19 C20 C21 C22 1.42(18) . . . . ?
C20 C21 C22 C17 -0.42(18) . . . . ?
C22 C17 C18 C19 1.81(17) . . . . ?
C23 P2 C17 C18 147.27(8) . . . . ?
C23 P2 C17 C22 -31.70(11) . . . . ?
C23 P2 C29 O4 63.32(10) . . . . ?
C23 P2 C29 N2 -116.04(8) . . . . ?
C23 C24 C25 C26 0.6(2) . . . . ?
C24 C23 C28 C27 -0.78(17) . . . . ?
C24 C25 C26 C27 -0.6(2) . . . . ?
C25 C26 C27 C28 0.0(2) . . . . ?
C26 C27 C28 C23 0.74(18) . . . . ?
C28 C23 C24 C25 0.13(19) . . . . ?
C29 P2 C17 C18 -100.32(9) . . . . ?
C29 P2 C17 C22 80.72(11) . . . . ?
C29 P2 C23 C24 -163.67(9) . . . . ?
C29 P2 C23 C28 25.62(10) . . . . ?
C29 N2 C30 C31 -85.00(13) . . . . ?
C30 N2 C29 P2 170.04(8) . . . . ?
C30 N2 C29 O4 -9.26(18) . . . . ?
P3 C33 C34 C35 178.15(9) . . . . ?
P3 C33 C38 C37 -177.87(9) . . . . ?
P3 C39 C40 C41 179.88(11) . . . . ?
P3 C39 C44 C43 -179.39(9) . . . . ?
O5 P3 C33 C34 0.19(11) . . . . ?
O5 P3 C33 C38 177.71(9) . . . . ?
O5 P3 C39 C40 -17.00(11) . . . . ?
O5 P3 C39 C44 162.28(9) . . . . ?
O5 P3 C45 O6 166.44(9) . . . . ?
O5 P3 C45 N3 -17.43(10) . . . . ?
N3 C46 C47 C48 68.79(14) . . . . ?
C33 P3 C39 C40 107.89(10) . . . . ?
C33 P3 C39 C44 -72.83(11) . . . . ?
C33 P3 C45 O6 41.57(11) . . . . ?
C33 P3 C45 N3 -142.30(9) . . . . ?
C33 C34 C35 C36 -0.24(19) . . . . ?
C34 C33 C38 C37 -0.42(17) . . . . ?
C34 C35 C36 C37 -0.16(19) . . . . ?
C35 C36 C37 C38 0.26(19) . . . . ?
C36 C37 C38 C33 0.03(18) . . . . ?
C38 C33 C34 C35 0.52(17) . . . . ?
C39 P3 C33 C34 -124.78(9) . . . . ?
C39 P3 C33 C38 52.74(11) . . . . ?
C39 P3 C45 O6 -71.83(10) . . . . ?
C39 P3 C45 N3 104.30(9) . . . . ?
C39 C40 C41 C42 -0.5(2) . . . . ?
C40 C39 C44 C43 -0.12(17) . . . . ?
C40 C41 C42 C43 -0.1(2) . . . . ?
C41 C42 C43 C44 0.51(19) . . . . ?
C42 C43 C44 C39 -0.41(18) . . . . ?
C44 C39 C40 C41 0.57(19) . . . . ?
C45 P3 C33 C34 125.39(9) . . . . ?
C45 P3 C33 C38 -57.09(11) . . . . ?
C45 P3 C39 C40 -139.01(10) . . . . ?
C45 P3 C39 C44 40.27(11) . . . . ?
C45 N3 C46 C47 -122.67(12) . . . . ?
C46 N3 C45 P3 -173.18(9) . . . . ?
C46 N3 C45 O6 2.65(19) . . . . ?
P4 C49 C50 C51 179.18(9) . . . . ?
P4 C49 C54 C53 -179.35(9) . . . . ?
P4 C55 C56 C57 -170.34(10) . . . . ?
P4 C55 C60 C59 169.94(10) . . . . ?
O7 P4 C49 C50 12.77(10) . . . . ?
O7 P4 C49 C54 -169.09(9) . . . . ?
O7 P4 C55 C56 91.83(10) . . . . ?
O7 P4 C55 C60 -79.33(10) . . . . ?
O7 P4 C61 O8 -168.99(9) . . . . ?
O7 P4 C61 N4 7.69(10) . . . . ?
N4 C62A C63A C64A 58.0(2) . . . . ?
N4 C62B C63B C64B -165.0(9) . . . . ?
C49 P4 C55 C56 -33.47(11) . . . . ?
C49 P4 C55 C60 155.37(9) . . . . ?
C49 P4 C61 O8 -47.47(10) . . . . ?
C49 P4 C61 N4 129.21(9) . . . . ?
C49 C50 C51 C52 0.00(17) . . . . ?
C50 C49 C54 C53 -1.27(17) . . . . ?
C50 C51 C52 C53 -0.66(17) . . . . ?
C51 C52 C53 C54 0.35(17) . . . . ?
C52 C53 C54 C49 0.61(17) . . . . ?
C54 C49 C50 C51 0.97(17) . . . . ?
C55 P4 C49 C50 138.58(9) . . . . ?
C55 P4 C49 C54 -43.28(11) . . . . ?
C55 P4 C61 O8 66.98(10) . . . . ?
C55 P4 C61 N4 -116.33(9) . . . . ?
C55 C56 C57 C58 0.59(19) . . . . ?
C56 C55 C60 C59 -1.39(18) . . . . ?
C56 C57 C58 C59 -1.3(2) . . . . ?
C57 C58 C59 C60 0.6(2) . . . . ?
C58 C59 C60 C55 0.72(19) . . . . ?
C60 C55 C56 C57 0.74(18) . . . . ?
C61 P4 C49 C50 -109.32(9) . . . . ?
C61 P4 C49 C54 68.83(10) . . . . ?
C61 P4 C55 C56 -144.17(9) . . . . ?
C61 P4 C55 C60 44.66(10) . . . . ?
C61 N4 C62A C63A -129.31(15) . . . . ?
C61 N4 C62B C63B -79.3(11) . . . . ?
C62A N4 C61 P4 -172.40(13) . . . . ?
C62A N4 C61 O8 4.0(2) . . . . ?
C62B N4 C61 P4 160.0(6) . . . . ?
C62B N4 C61 O8 -23.6(6) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.9973 2.9997 -0.0003 0.2352 -0.0418 0.6047
1.9986 -1.0014 -4.9962 0.3862 -0.0541 -0.3320
1.9984 -2.0010 -4.9962 0.4280 0.0391 -0.3812
-3.9984 0.9988 -4.9965 0.7354 0.0448 0.3149
2.9978 -3.0007 -4.9961 0.3977 0.0847 -0.5219
1.9983 -3.0006 -4.9961 0.4698 0.1322 -0.4305
4.9979 0.9984 -0.9993 -0.3048 -0.3413 -0.4277
-0.0010 -4.9985 -1.9982 0.4046 0.4450 -0.2863
0.9986 -4.9984 -0.9989 0.2348 0.4079 -0.3577
-0.9986 4.9984 0.9989 -0.2348 -0.4079 0.3577
-1.9999 -4.9976 0.0004 0.3535 0.5610 -0.0635
1.9999 4.9976 -0.0004 -0.3535 -0.5610 0.0635
-1.9999 -4.9973 0.9996 0.2558 0.5714 -0.0436
1.9999 4.9973 -0.9996 -0.2558 -0.5714 0.0436
0.0002 0.9996 -0.0001 -0.0418 -0.0932 0.0493
-1.0003 -4.9974 0.9996 0.1836 0.5239 -0.1349
-1.9997 -4.9967 2.9982 0.0603 0.5923 -0.0036
3.9973 -4.9989 -0.9988 0.0183 0.2653 -0.6319
-2.9981 1.0016 4.9962 -0.3140 0.1017 0.4233
4.9972 -2.9999 -0.9990 -0.1375 0.0314 -0.6247
3.9981 -2.9980 4.9966 -0.6517 0.1416 -0.4134
