#------------------------------------------------------------------------------
#$Date: 2020-07-02 04:30:46 +0300 (Thu, 02 Jul 2020) $
#$Revision: 253646 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/84/1558465.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_1558465
loop_
_publ_author_name
'Jin, Shengfei'
'Dang, Hang T.'
'Haug, Graham C.'
'Nguyen, Viet D.'
'Arman, Hadi'
'Larionov, Oleg V.'
_publ_section_title
;
 Deoxygenative α-Alkylation and α-Arylation of 1,2-Dicarbonyls
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03118F
_journal_year                    2020
_chemical_formula_moiety         'C28 H47 B N3 O2 P'
_chemical_formula_sum            'C28 H47 B N3 O2 P'
_chemical_formula_weight         499.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-16
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_audit_update_record
;
2020-03-27 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.889(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3547(2)
_cell_length_b                   17.4727(4)
_cell_length_c                   14.7370(2)
_cell_measurement_reflns_used    11295
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3400
_cell_measurement_theta_min      3.9410
_cell_volume                     2880.34(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00 120.00   0.50    0.40    --   46.62  55.00 -28.62  178
  2  ω     81.00 169.00   0.50    1.60    --  106.69 146.00-172.00  176
  3  ω     91.00 178.00   0.50    1.60    --  106.69  30.00 120.00  174
  4  ω     46.00 127.00   0.50    1.60    --  106.69-146.00 136.00  162
  5  ω     46.00 108.00   0.50    0.40    --   46.62-146.00 136.00  124
  6  ω     34.00 101.00   0.50    1.60    --  106.69 -77.00  90.00  134
  7  ω     34.00  71.00   0.50    1.60    --  106.69 -61.00  90.00   74
  8  ω     34.00  71.00   0.50    1.60    --  106.69 -61.00 120.00   74
  9  ω     34.00  95.00   0.50    0.40    --   46.62-124.00 -57.00  122
 10  ω     34.00 111.00   0.50    1.60    --  106.69-124.00 -57.00  154
 11  ω     34.00  71.00   0.50    1.60    --  106.69 -61.00 -60.00   74
 12  ω     34.00 101.00   0.50    1.60    --  106.69 -77.00 -60.00  134
 13  ω     34.00 105.00   0.50    1.60    --  106.69 -94.00 -60.00  142
 14  ω     34.00  71.00   0.50    1.60    --  106.69 -61.00-180.00   74
 15  ω    -85.00 -12.00   0.50    0.40    --  -46.62 124.00  21.00  146
 16  ω    -51.00 -16.00   0.50    1.60    --  -88.50  45.00-180.00   70
 17  ω    -51.00 -16.00   0.50    1.60    --  -88.50  45.00-150.00   70
 18  ω    -51.00 -16.00   0.50    1.60    --  -88.50  45.00-120.00   70
 19  ω    -51.00 -16.00   0.50    1.60    --  -88.50  45.00 -60.00   70
 20  ω   -102.00 -24.00   0.50    1.60    --  -88.50 146.00-172.00  156
 21  ω   -119.00 -83.00   0.50    0.40    --  -46.62 -57.00 120.00   72
 22  ω   -119.00 -83.00   0.50    0.40    --  -46.62 -57.00 150.00   72
 23  ω   -119.00 -87.00   0.50    0.40    --  -46.62-125.00  60.00   64
 24  ω   -119.00 -59.00   0.50    0.40    --  -46.62-146.00 136.00  120
 25  ω   -160.00 -74.00   0.50    1.60    --  -88.50-124.00 -57.00  172
 26  ω   -119.00 -83.00   0.50    0.40    --  -46.62 -57.00-150.00   72
 27  ω   -119.00 -83.00   0.50    0.40    --  -46.62 -57.00-180.00   72
 28  ω   -119.00 -83.00   0.50    0.40    --  -46.62 -57.00 -90.00   72
 29  ω   -160.00-101.00   0.50    1.60    --  -88.50 -77.00  60.00  118
 30  ω    -51.00 -16.00   0.50    1.60    --  -88.50  45.00 150.00   70
 31  ω    -71.00 -15.00   0.50    1.60    --  -88.50  61.00 120.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0399995000
_diffrn_orient_matrix_UB_12      -0.0836636000
_diffrn_orient_matrix_UB_13      0.0195920000
_diffrn_orient_matrix_UB_21      0.1285665000
_diffrn_orient_matrix_UB_22      0.0272925000
_diffrn_orient_matrix_UB_23      0.0349577000
_diffrn_orient_matrix_UB_31      -0.0283113000
_diffrn_orient_matrix_UB_32      0.0069478000
_diffrn_orient_matrix_UB_33      0.0982160000
_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  0.0396
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32219
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.534
_diffrn_reflns_theta_min         3.952
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.055
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.513
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_description       plank
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0466
_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)+(0.0500P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1165
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5058
_reflns_number_total             5795
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc03118f2.cif
_cod_data_source_block           hpd107
_cod_database_code               1558465
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H20N2O4
_chemical_oxdiff_usercomment     'air sensitive sample'
_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   0.950
_shelx_estimated_absorpt_t_min   0.773
_reflns_odcompleteness_completeness 99.94
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C23(H23A,H23B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C6(H6), C4(H4), C11(H11), C15(H15), C12(H12), C14(H14)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C8(H8A,H8B,H8C), C22(H22A,H22B,H22C), C19(H19A,H19B,
 H19C), C21(H21A,H21B,H21C), C18(H18A,H18B,H18C), C16(H16A,H16B,H16C), C26(H26A,
 H26B,H26C), C24(H24A,H24B,H24C), C20(H20A,H20B,H20C), C28(H28A,H28B,H28C)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.223
_oxdiff_exptl_absorpt_empirical_full_min 0.792
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.31607(4) 0.56586(2) 0.70400(3) 0.02558(12) Uani 1 1 d . . . . .
O1 O 0.37083(10) 0.58026(7) 0.61371(7) 0.0265(2) Uani 1 1 d . . . . .
O2 O 0.61372(10) 0.71680(7) 0.62778(8) 0.0284(3) Uani 1 1 d . . . . .
N1 N 0.28023(13) 0.64268(8) 0.75397(9) 0.0297(3) Uani 1 1 d . . . . .
N3 N 0.41021(13) 0.51936(8) 0.77819(9) 0.0293(3) Uani 1 1 d . . . . .
N2 N 0.20212(13) 0.51246(9) 0.66616(10) 0.0311(3) Uani 1 1 d . . . . .
C2 C 0.35382(15) 0.71601(10) 0.56930(10) 0.0275(3) Uani 1 1 d . . . . .
C10 C 0.62342(15) 0.58163(10) 0.66192(11) 0.0286(3) Uani 1 1 d . . . . .
C3 C 0.39148(15) 0.79283(10) 0.57880(11) 0.0288(3) Uani 1 1 d . . . . .
H3 H 0.470771 0.804292 0.607957 0.035 Uiso 1 1 calc R U . . .
C5 C 0.19755(15) 0.83859(10) 0.50170(11) 0.0287(3) Uani 1 1 d . . . . .
C9 C 0.55353(15) 0.65240(10) 0.62829(11) 0.0281(3) Uani 1 1 d . . . . .
C1 C 0.43280(15) 0.65227(10) 0.60462(11) 0.0276(3) Uani 1 1 d . . . . .
C7 C 0.23529(15) 0.70314(10) 0.52598(11) 0.0295(4) Uani 1 1 d . . . . .
H7 H 0.206168 0.652126 0.519262 0.035 Uiso 1 1 calc R U . . .
C6 C 0.15953(16) 0.76302(10) 0.49271(11) 0.0309(4) Uani 1 1 d . . . . .
H6 H 0.080191 0.752045 0.463237 0.037 Uiso 1 1 calc R U . . .
C4 C 0.31428(15) 0.85192(10) 0.54613(11) 0.0289(3) Uani 1 1 d . . . . .
H4 H 0.341865 0.903207 0.554293 0.035 Uiso 1 1 calc R U . . .
C11 C 0.68841(15) 0.58024(10) 0.75132(11) 0.0303(4) Uani 1 1 d . . . . .
H11 H 0.682137 0.621940 0.791574 0.036 Uiso 1 1 calc R U . . .
C15 C 0.63228(16) 0.51916(10) 0.60519(12) 0.0322(4) Uani 1 1 d . . . . .
H15 H 0.588352 0.518730 0.544212 0.039 Uiso 1 1 calc R U . . .
C13 C 0.77179(16) 0.45607(11) 0.72529(13) 0.0341(4) Uani 1 1 d . . . . .
C12 C 0.76180(16) 0.51910(11) 0.78225(12) 0.0335(4) Uani 1 1 d . . . . .
H12 H 0.806144 0.519858 0.843094 0.040 Uiso 1 1 calc R U . . .
C25 C 0.72934(16) 0.82440(10) 0.57684(12) 0.0336(4) Uani 1 1 d . . . . .
H25A H 0.652860 0.840583 0.538881 0.040 Uiso 1 1 calc R U . . .
H25B H 0.732034 0.845797 0.639366 0.040 Uiso 1 1 calc R U . . .
C17 C 0.36966(17) 0.69756(11) 0.79916(12) 0.0348(4) Uani 1 1 d . . . . .
H17A H 0.449506 0.674776 0.805394 0.052 Uiso 1 1 calc R U . . .
H17B H 0.352451 0.710294 0.860316 0.052 Uiso 1 1 calc R U . . .
H17C H 0.366615 0.744199 0.761886 0.052 Uiso 1 1 calc R U . . .
C14 C 0.70479(16) 0.45723(11) 0.63678(13) 0.0354(4) Uani 1 1 d . . . . .
H14 H 0.708720 0.414794 0.597114 0.042 Uiso 1 1 calc R U . . .
C8 C 0.11593(16) 0.90406(11) 0.46606(12) 0.0349(4) Uani 1 1 d . . . . .
H8A H 0.044379 0.884021 0.426459 0.052 Uiso 1 1 calc R U . . .
H8B H 0.157844 0.939034 0.430497 0.052 Uiso 1 1 calc R U . . .
H8C H 0.092552 0.931642 0.518083 0.052 Uiso 1 1 calc R U . . .
C22 C 0.43064(17) 0.52938(12) 0.87856(11) 0.0366(4) Uani 1 1 d . . . . .
H22A H 0.382014 0.572073 0.894435 0.055 Uiso 1 1 calc R U . . .
H22B H 0.515370 0.540357 0.900581 0.055 Uiso 1 1 calc R U . . .
H22C H 0.408188 0.482407 0.907679 0.055 Uiso 1 1 calc R U . . .
C19 C 0.13638(17) 0.50889(11) 0.57207(12) 0.0375(4) Uani 1 1 d . . . . .
H19A H 0.066489 0.542596 0.566154 0.056 Uiso 1 1 calc R U . . .
H19B H 0.110079 0.456194 0.557654 0.056 Uiso 1 1 calc R U . . .
H19C H 0.188407 0.525495 0.529207 0.056 Uiso 1 1 calc R U . . .
C23 C 0.71652(17) 0.69003(11) 0.48342(12) 0.0348(4) Uani 1 1 d . . . . .
H23A H 0.791363 0.697661 0.458631 0.042 Uiso 1 1 calc R U . . .
H23B H 0.706737 0.634320 0.491889 0.042 Uiso 1 1 calc R U . . .
C27 C 0.84955(16) 0.70000(12) 0.65191(13) 0.0367(4) Uani 1 1 d . . . . .
H27A H 0.842847 0.643758 0.657401 0.044 Uiso 1 1 calc R U . . .
H27B H 0.920253 0.710624 0.622872 0.044 Uiso 1 1 calc R U . . .
C21 C 0.45651(17) 0.44659(10) 0.74828(12) 0.0339(4) Uani 1 1 d . . . . .
H21A H 0.417051 0.403790 0.773883 0.051 Uiso 1 1 calc R U . . .
H21B H 0.542923 0.443793 0.770174 0.051 Uiso 1 1 calc R U . . .
H21C H 0.440397 0.443733 0.680870 0.051 Uiso 1 1 calc R U . . .
C18 C 0.15803(16) 0.67305(11) 0.73613(12) 0.0354(4) Uani 1 1 d . . . . .
H18A H 0.153096 0.714842 0.691277 0.053 Uiso 1 1 calc R U . . .
H18B H 0.136966 0.692350 0.793696 0.053 Uiso 1 1 calc R U . . .
H18C H 0.102373 0.632264 0.711479 0.053 Uiso 1 1 calc R U . . .
C16 C 0.84867(19) 0.38847(12) 0.75938(15) 0.0438(5) Uani 1 1 d . . . . .
H16A H 0.921276 0.406244 0.799663 0.066 Uiso 1 1 calc R U . . .
H16B H 0.870564 0.360920 0.706795 0.066 Uiso 1 1 calc R U . . .
H16C H 0.804285 0.354171 0.793928 0.066 Uiso 1 1 calc R U . . .
C26 C 0.83233(19) 0.85867(12) 0.53548(15) 0.0425(5) Uani 1 1 d . . . . .
H26A H 0.829305 0.839098 0.472807 0.064 Uiso 1 1 calc R U . . .
H26B H 0.908629 0.844302 0.573465 0.064 Uiso 1 1 calc R U . . .
H26C H 0.824992 0.914557 0.533696 0.064 Uiso 1 1 calc R U . . .
C24 C 0.61196(18) 0.71862(12) 0.41218(13) 0.0411(4) Uani 1 1 d . . . . .
H24A H 0.615294 0.694845 0.352444 0.062 Uiso 1 1 calc R U . . .
H24B H 0.617016 0.774362 0.406545 0.062 Uiso 1 1 calc R U . . .
H24C H 0.536477 0.705002 0.431839 0.062 Uiso 1 1 calc R U . . .
C20 C 0.14145(18) 0.47272(12) 0.73336(14) 0.0421(5) Uani 1 1 d . . . . .
H20A H 0.191807 0.474755 0.794388 0.063 Uiso 1 1 calc R U . . .
H20B H 0.127396 0.419206 0.714699 0.063 Uiso 1 1 calc R U . . .
H20C H 0.064817 0.497784 0.735684 0.063 Uiso 1 1 calc R U . . .
C28 C 0.87115(18) 0.73456(13) 0.74885(13) 0.0435(5) Uani 1 1 d . . . . .
H28A H 0.906244 0.785658 0.746952 0.065 Uiso 1 1 calc R U . . .
H28B H 0.926028 0.701707 0.790308 0.065 Uiso 1 1 calc R U . . .
H28C H 0.794995 0.738447 0.771329 0.065 Uiso 1 1 calc R U . . .
B1 B 0.73079(17) 0.73142(12) 0.58387(13) 0.0303(4) Uani 1 1 d . . . . .
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'
B B 0.0090 0.0039 '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
-2 1 10 0.1243
7 1 0 0.0529
-7 -1 0 0.0249
1 -11 0 0.0188
3 1 -9 0.1126
-1 11 1 0.0191
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 N1 114.65(7) . . ?
O1 P1 N3 109.87(7) . . ?
O1 P1 N2 102.04(7) . . ?
N3 P1 N1 107.41(7) . . ?
N3 P1 N2 109.98(8) . . ?
N2 P1 N1 112.81(8) . . ?
C1 O1 P1 118.66(10) . . ?
C9 O2 B1 127.46(13) . . ?
C17 N1 P1 122.66(12) . . ?
C18 N1 P1 121.56(12) . . ?
C18 N1 C17 113.81(14) . . ?
C22 N3 P1 126.52(12) . . ?
C22 N3 C21 113.70(14) . . ?
C21 N3 P1 117.50(11) . . ?
C19 N2 P1 127.00(12) . . ?
C19 N2 C20 113.37(14) . . ?
C20 N2 P1 118.64(12) . . ?
C3 C2 C1 122.09(15) . . ?
C7 C2 C3 116.64(15) . . ?
C7 C2 C1 121.26(15) . . ?
C11 C10 C9 119.23(15) . . ?
C15 C10 C9 122.38(15) . . ?
C15 C10 C11 118.25(16) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.82(16) . . ?
C4 C3 H3 119.6 . . ?
C6 C5 C4 117.32(16) . . ?
C6 C5 C8 121.70(16) . . ?
C4 C5 C8 120.97(16) . . ?
O2 C9 C10 117.29(14) . . ?
O2 C9 C1 120.19(15) . . ?
C1 C9 C10 122.39(15) . . ?
O1 C1 C2 114.32(14) . . ?
C9 C1 O1 117.41(15) . . ?
C9 C1 C2 128.26(16) . . ?
C2 C7 H7 119.1 . . ?
C6 C7 C2 121.78(16) . . ?
C6 C7 H7 119.1 . . ?
C5 C6 C7 121.26(16) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C3 C4 C5 122.17(16) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.05(16) . . ?
C12 C11 H11 119.5 . . ?
C10 C15 H15 119.7 . . ?
C10 C15 C14 120.66(16) . . ?
C14 C15 H15 119.7 . . ?
C12 C13 C16 121.30(17) . . ?
C14 C13 C12 117.53(16) . . ?
C14 C13 C16 121.13(18) . . ?
C11 C12 C13 121.05(16) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
H25A C25 H25B 107.6 . . ?
C26 C25 H25A 108.6 . . ?
C26 C25 H25B 108.6 . . ?
C26 C25 B1 114.57(16) . . ?
B1 C25 H25A 108.6 . . ?
B1 C25 H25B 108.6 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C14 C13 121.44(17) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H23A C23 H23B 107.5 . . ?
C24 C23 H23A 108.5 . . ?
C24 C23 H23B 108.5 . . ?
C24 C23 B1 115.04(15) . . ?
B1 C23 H23A 108.5 . . ?
B1 C23 H23B 108.5 . . ?
H27A C27 H27B 107.5 . . ?
C28 C27 H27A 108.5 . . ?
C28 C27 H27B 108.5 . . ?
C28 C27 B1 115.07(16) . . ?
B1 C27 H27A 108.5 . . ?
B1 C27 H27B 108.5 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O2 B1 C25 100.69(13) . . ?
O2 B1 C23 109.72(14) . . ?
O2 B1 C27 110.80(14) . . ?
C25 B1 C23 112.74(15) . . ?
C25 B1 C27 111.92(15) . . ?
C23 B1 C27 110.58(15) . . ?
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 1.5826(11) . ?
P1 N1 1.6163(15) . ?
P1 N3 1.6114(14) . ?
P1 N2 1.6149(15) . ?
O1 C1 1.459(2) . ?
O2 C9 1.317(2) . ?
O2 B1 1.596(2) . ?
N1 C17 1.470(2) . ?
N1 C18 1.467(2) . ?
N3 C22 1.468(2) . ?
N3 C21 1.472(2) . ?
N2 C19 1.459(2) . ?
N2 C20 1.474(2) . ?
C2 C3 1.408(2) . ?
C2 C1 1.468(2) . ?
C2 C7 1.405(2) . ?
C10 C9 1.506(2) . ?
C10 C11 1.395(2) . ?
C10 C15 1.389(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C5 C6 1.388(2) . ?
C5 C4 1.393(2) . ?
C5 C8 1.509(2) . ?
C9 C1 1.355(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.389(2) . ?
C6 H6 0.9500 . ?
C4 H4 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.383(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.391(3) . ?
C13 C12 1.401(3) . ?
C13 C14 1.393(3) . ?
C13 C16 1.503(3) . ?
C12 H12 0.9500 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.530(3) . ?
C25 B1 1.628(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C14 H14 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.528(3) . ?
C23 B1 1.630(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.532(3) . ?
C27 B1 1.631(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
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 O1 C1 C2 -84.03(14) . . . . ?
P1 O1 C1 C9 96.57(15) . . . . ?
O1 P1 N1 C17 -67.85(14) . . . . ?
O1 P1 N1 C18 95.16(14) . . . . ?
O1 P1 N3 C22 143.69(15) . . . . ?
O1 P1 N3 C21 -54.57(14) . . . . ?
O1 P1 N2 C19 -25.14(17) . . . . ?
O1 P1 N2 C20 167.03(14) . . . . ?
O2 C9 C1 O1 -175.19(13) . . . . ?
O2 C9 C1 C2 5.5(3) . . . . ?
N1 P1 O1 C1 26.90(13) . . . . ?
N1 P1 N3 C22 18.37(17) . . . . ?
N1 P1 N3 C21 -179.89(13) . . . . ?
N1 P1 N2 C19 98.39(16) . . . . ?
N1 P1 N2 C20 -69.44(16) . . . . ?
N3 P1 O1 C1 -94.16(12) . . . . ?
N3 P1 N1 C17 54.55(15) . . . . ?
N3 P1 N1 C18 -142.43(13) . . . . ?
N3 P1 N2 C19 -141.72(15) . . . . ?
N3 P1 N2 C20 50.45(16) . . . . ?
N2 P1 O1 C1 149.18(11) . . . . ?
N2 P1 N1 C17 175.91(13) . . . . ?
N2 P1 N1 C18 -21.07(16) . . . . ?
N2 P1 N3 C22 -104.75(16) . . . . ?
N2 P1 N3 C21 56.99(15) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C2 C7 C6 C5 -0.6(2) . . . . ?
C10 C9 C1 O1 0.6(2) . . . . ?
C10 C9 C1 C2 -178.67(15) . . . . ?
C10 C11 C12 C13 -1.0(3) . . . . ?
C10 C15 C14 C13 -0.8(3) . . . . ?
C3 C2 C1 O1 162.67(14) . . . . ?
C3 C2 C1 C9 -18.0(3) . . . . ?
C3 C2 C7 C6 1.1(2) . . . . ?
C9 O2 B1 C25 161.68(14) . . . . ?
C9 O2 B1 C23 42.6(2) . . . . ?
C9 O2 B1 C27 -79.8(2) . . . . ?
C9 C10 C11 C12 -174.43(16) . . . . ?
C9 C10 C15 C14 175.20(16) . . . . ?
C1 C2 C3 C4 -178.91(15) . . . . ?
C1 C2 C7 C6 179.67(15) . . . . ?
C7 C2 C3 C4 -0.3(2) . . . . ?
C7 C2 C1 O1 -15.8(2) . . . . ?
C7 C2 C1 C9 163.48(16) . . . . ?
C6 C5 C4 C3 1.3(2) . . . . ?
C4 C5 C6 C7 -0.6(2) . . . . ?
C11 C10 C9 O2 59.4(2) . . . . ?
C11 C10 C9 C1 -116.51(19) . . . . ?
C11 C10 C15 C14 -0.5(3) . . . . ?
C15 C10 C9 O2 -116.18(18) . . . . ?
C15 C10 C9 C1 67.9(2) . . . . ?
C15 C10 C11 C12 1.4(3) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C14 C13 C12 C11 -0.3(3) . . . . ?
C8 C5 C6 C7 -179.82(15) . . . . ?
C8 C5 C4 C3 -179.41(15) . . . . ?
C16 C13 C12 C11 -178.23(17) . . . . ?
C16 C13 C14 C15 179.15(17) . . . . ?
C26 C25 B1 O2 -179.50(14) . . . . ?
C26 C25 B1 C23 -62.7(2) . . . . ?
C26 C25 B1 C27 62.8(2) . . . . ?
C24 C23 B1 O2 60.9(2) . . . . ?
C24 C23 B1 C25 -50.5(2) . . . . ?
C24 C23 B1 C27 -176.60(15) . . . . ?
C28 C27 B1 O2 -57.5(2) . . . . ?
C28 C27 B1 C25 54.0(2) . . . . ?
C28 C27 B1 C23 -179.41(16) . . . . ?
B1 O2 C9 C10 51.2(2) . . . . ?
B1 O2 C9 C1 -132.81(16) . . . . ?
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
-1.8171 0.9754 9.5035 0.0319 0.1252 0.9916
7.1788 0.7860 0.4837 0.2309 0.9613 -0.1503
-7.2941 -0.6990 0.3250 -0.2269 -0.9455 0.2336
0.6235 -11.2848 -0.1254 0.9666 -0.2322 -0.1084
2.6093 1.4798 -9.3114 -0.2019 0.0504 -0.9781
-0.8826 11.1974 1.0392 -0.9518 0.2285 0.2049
