#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:05:20 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286028 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/93/1569386.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_1569386
loop_
_publ_author_name
'Löwe, Pawel'
'Wünsche, Marius A'
'Purtscher, Felix R. S.'
'Gamper, Jakob'
'Hofer, Thomas S.'
'Wilm, Lukas F. B.'
'Röthel, Maike B'
'Dielmann, Fabian'
_publ_section_title
;
 Terminal methylene phosphonium ions: precursors for transient
 monosubstituted phosphinocarbenes.
;
_journal_issue                   29
_journal_name_full               'Chemical science'
_journal_page_first              7928
_journal_page_last               7935
_journal_paper_doi               10.1039/d3sc02899b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C55 H73 N6 P'
_chemical_formula_sum            'C55 H73 N6 P'
_chemical_formula_weight         849.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2023-02-23 deposited with the CCDC.	2023-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.9440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9765(2)
_cell_length_b                   20.2016(4)
_cell_length_c                   20.2590(4)
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.27
_cell_volume                     5131.20(17)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            73164
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.346
_diffrn_reflns_theta_min         1.449
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1119 before and 0.0558 after correction. The Ratio of minimum to maximum transmission is 0.6985. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     626
_refine_ls_number_reflns         12743
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0606
_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)+(0.0736P)²+2.3079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1534
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9461
_reflns_number_total             12743
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc02899b2.cif
_cod_data_source_block           p21n_a
_cod_depositor_comments
'Adding full bibliography for 1569380--1569388.cif.'
_cod_database_code               1569386
_shelxl_version_number           2013-4
_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   0.990
_shelx_estimated_absorpt_t_min   0.975
_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. Uiso/Uaniso restraints and constraints
Uanis(C38A) \\sim Ueq, Uanis(C42A) \\sim Ueq, Uanis(C43A) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
3. Others
 Sof(H41A)=Sof(C42A)=Sof(H42D)=Sof(H42E)=Sof(H42F)=Sof(C43A)=Sof(H43D)=
 Sof(H43E)=Sof(H43F)=1-FVAR(1)
 Sof(H41)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(H42C)=Sof(C43)=Sof(H43A)=Sof(H43B)=
 Sof(H43C)=FVAR(1)
 Sof(C38A)=Sof(H38A)=Sof(C39B)=Sof(H39A)=Sof(H39B)=Sof(H39C)=Sof(C40B)=
 Sof(H40A)=Sof(H40B)=Sof(H40C)=1-FVAR(2)
 Sof(C38B)=Sof(H38B)=Sof(C39A)=Sof(H39D)=Sof(H39E)=Sof(H39F)=Sof(C40A)=
 Sof(H40D)=Sof(H40E)=Sof(H40F)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C5(H5), C11(H11), C14(H14), C23(H23), C26(H26), C38B(H38B), C38A(H38A),
 C41(H41), C41(H41A), C50(H50), C53(H53)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C19(H19), C20(H20), C21(H21),
 C30(H30), C31(H31), C34(H34), C35(H35), C36(H36), C46(H46), C47(H47), C48(H48)
4.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,
 H28B,H28C), C39A(H39D,H39E,H39F), C39B(H39A,H39B,H39C), C40A(H40D,H40E,H40F),
 C40B(H40A,H40B,H40C), C42(H42A,H42B,H42C), C42A(H42D,H42E,H42F), C43(H43A,H43B,
 H43C), C43A(H43D,H43E,H43F), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C),
 C54(H54A,H54B,H54C), C55(H55A,H55B,H55C)
;
_olex2_date_sample_data_collection 2018-02-18
_olex2_date_sample_submission    2018-02-18
_olex2_submission_original_sample_id maw180218
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.54271(3) 0.33519(2) 0.28194(2) 0.01698(10) Uani 1 1 d . . . . .
N1 N 0.43589(11) 0.38202(7) 0.24183(7) 0.0202(3) Uani 1 1 d . . . . .
N2 N 0.33982(11) 0.48142(7) 0.24372(7) 0.0204(3) Uani 1 1 d . . . . .
N3 N 0.49849(11) 0.47626(7) 0.31675(7) 0.0188(3) Uani 1 1 d . . . . .
N4 N 0.58352(11) 0.30051(7) 0.21691(7) 0.0191(3) Uani 1 1 d . . . . .
N5 N 0.52530(11) 0.18633(7) 0.22865(7) 0.0197(3) Uani 1 1 d . . . . .
N6 N 0.64621(11) 0.20424(7) 0.17398(8) 0.0217(3) Uani 1 1 d . . . . .
C1 C 0.42669(13) 0.43983(8) 0.26583(8) 0.0182(3) Uani 1 1 d . . . . .
C2 C 0.36040(14) 0.54260(9) 0.27590(9) 0.0222(4) Uani 1 1 d . . . . .
H2 H 0.3136 0.5796 0.2683 0.027 Uiso 1 1 calc R . . . .
C3 C 0.45658(14) 0.54050(9) 0.31906(9) 0.0222(4) Uani 1 1 d . . . . .
H3 H 0.4913 0.5761 0.3467 0.027 Uiso 1 1 calc R . . . .
C4 C 0.60400(13) 0.45541(8) 0.34687(8) 0.0183(3) Uani 1 1 d . . . . .
C5 C 0.64607(13) 0.40069(8) 0.31024(9) 0.0183(3) Uani 1 1 d . . . . .
H5 H 0.7039 0.3791 0.3461 0.022 Uiso 1 1 calc R . . . .
C6 C 0.70315(14) 0.43717(8) 0.26503(9) 0.0211(4) Uani 1 1 d . . . . .
C7 C 0.79995(14) 0.46225(9) 0.29764(10) 0.0243(4) Uani 1 1 d . . . . .
H7 H 0.8439 0.4783 0.2702 0.029 Uiso 1 1 calc R . . . .
C8 C 0.84080(14) 0.46633(9) 0.37032(10) 0.0265(4) Uani 1 1 d . . . . .
H8 H 0.9160 0.4631 0.3876 0.032 Uiso 1 1 calc R . . . .
C9 C 0.78285(14) 0.47436(9) 0.41728(9) 0.0249(4) Uani 1 1 d . . . . .
H9 H 0.8219 0.4742 0.4639 0.030 Uiso 1 1 calc R . . . .
C10 C 0.66932(14) 0.48301(9) 0.40405(9) 0.0211(4) Uani 1 1 d . . . . .
C11 C 0.62846(14) 0.52267(9) 0.45620(9) 0.0243(4) Uani 1 1 d . . . . .
H11 H 0.5489 0.5242 0.4399 0.029 Uiso 1 1 calc R . . . .
C12 C 0.65673(16) 0.48746(12) 0.52548(10) 0.0345(5) Uani 1 1 d . . . . .
H12A H 0.6244 0.4433 0.5205 0.052 Uiso 1 1 calc GR . . . .
H12B H 0.6295 0.5132 0.5583 0.052 Uiso 1 1 calc GR . . . .
H12C H 0.7344 0.4834 0.5419 0.052 Uiso 1 1 calc GR . . . .
C13 C 0.66874(17) 0.59413(10) 0.46356(11) 0.0333(5) Uani 1 1 d . . . . .
H13A H 0.7464 0.5943 0.4817 0.050 Uiso 1 1 calc GR . . . .
H13B H 0.6358 0.6180 0.4949 0.050 Uiso 1 1 calc GR . . . .
H13C H 0.6498 0.6158 0.4188 0.050 Uiso 1 1 calc GR . . . .
C14 C 0.65291(15) 0.44766(9) 0.18939(9) 0.0263(4) Uani 1 1 d . . . . .
H14 H 0.5877 0.4193 0.1759 0.032 Uiso 1 1 calc R . . . .
C15 C 0.61852(18) 0.51987(11) 0.17527(11) 0.0372(5) Uani 1 1 d . . . . .
H15A H 0.5685 0.5318 0.2023 0.056 Uiso 1 1 calc GR . . . .
H15B H 0.5836 0.5254 0.1266 0.056 Uiso 1 1 calc GR . . . .
H15C H 0.6814 0.5486 0.1880 0.056 Uiso 1 1 calc GR . . . .
C16 C 0.72805(18) 0.42711(11) 0.14638(11) 0.0362(5) Uani 1 1 d . . . . .
H16A H 0.7912 0.4557 0.1572 0.054 Uiso 1 1 calc GR . . . .
H16B H 0.6914 0.4315 0.0978 0.054 Uiso 1 1 calc GR . . . .
H16C H 0.7499 0.3810 0.1564 0.054 Uiso 1 1 calc GR . . . .
C17 C 0.23882(14) 0.46186(9) 0.20022(9) 0.0230(4) Uani 1 1 d . . . . .
C18 C 0.22084(16) 0.46854(10) 0.12960(10) 0.0291(4) Uani 1 1 d . . . . .
C19 C 0.12006(17) 0.45064(11) 0.08965(11) 0.0376(5) Uani 1 1 d . . . . .
H19 H 0.1048 0.4545 0.0414 0.045 Uiso 1 1 calc R . . . .
C20 C 0.04232(17) 0.42750(11) 0.11897(12) 0.0385(5) Uani 1 1 d . . . . .
H20 H -0.0258 0.4159 0.0907 0.046 Uiso 1 1 calc R . . . .
C21 C 0.06226(16) 0.42102(11) 0.18891(11) 0.0341(5) Uani 1 1 d . . . . .
H21 H 0.0079 0.4047 0.2083 0.041 Uiso 1 1 calc R . . . .
C22 C 0.16114(14) 0.43807(9) 0.23139(10) 0.0254(4) Uani 1 1 d . . . . .
C23 C 0.18640(14) 0.42875(10) 0.30841(10) 0.0266(4) Uani 1 1 d . . . . .
H23 H 0.2469 0.4591 0.3294 0.032 Uiso 1 1 calc R . . . .
C24 C 0.09444(17) 0.44596(12) 0.33927(12) 0.0395(5) Uani 1 1 d . . . . .
H24A H 0.0734 0.4921 0.3288 0.059 Uiso 1 1 calc GR . . . .
H24B H 0.1171 0.4399 0.3889 0.059 Uiso 1 1 calc GR . . . .
H24C H 0.0337 0.4169 0.3199 0.059 Uiso 1 1 calc GR . . . .
C25 C 0.22419(18) 0.35813(11) 0.32780(11) 0.0372(5) Uani 1 1 d . . . . .
H25A H 0.1654 0.3272 0.3100 0.056 Uiso 1 1 calc GR . . . .
H25B H 0.2477 0.3543 0.3777 0.056 Uiso 1 1 calc GR . . . .
H25C H 0.2838 0.3476 0.3081 0.056 Uiso 1 1 calc GR . . . .
C26 C 0.30759(18) 0.49268(11) 0.09773(10) 0.0358(5) Uani 1 1 d . . . . .
H26 H 0.3652 0.5128 0.1349 0.043 Uiso 1 1 calc R . . . .
C27 C 0.2673(2) 0.54595(12) 0.04371(13) 0.0507(6) Uani 1 1 d . . . . .
H27A H 0.2153 0.5265 0.0046 0.076 Uiso 1 1 calc GR . . . .
H27B H 0.3274 0.5640 0.0286 0.076 Uiso 1 1 calc GR . . . .
H27C H 0.2332 0.5815 0.0633 0.076 Uiso 1 1 calc GR . . . .
C28 C 0.35641(19) 0.43487(12) 0.06795(12) 0.0428(5) Uani 1 1 d . . . . .
H28A H 0.3866 0.4030 0.1042 0.064 Uiso 1 1 calc GR . . . .
H28B H 0.4129 0.4513 0.0482 0.064 Uiso 1 1 calc GR . . . .
H28C H 0.3011 0.4132 0.0323 0.064 Uiso 1 1 calc GR . . . .
C29 C 0.58293(13) 0.23693(8) 0.20904(8) 0.0179(3) Uani 1 1 d . . . . .
C30 C 0.55588(15) 0.12523(9) 0.20777(10) 0.0266(4) Uani 1 1 d . . . . .
H30 H 0.5289 0.0832 0.2163 0.032 Uiso 1 1 calc R . . . .
C31 C 0.62939(15) 0.13611(9) 0.17384(10) 0.0271(4) Uani 1 1 d . . . . .
H31 H 0.6640 0.1035 0.1534 0.033 Uiso 1 1 calc R . . . .
C32 C 0.72001(15) 0.23451(9) 0.14100(10) 0.0266(4) Uani 1 1 d . . . . .
C33 C 0.68273(18) 0.25222(10) 0.07260(11) 0.0338(5) Uani 1 1 d . . . . .
C34 C 0.7580(2) 0.27564(11) 0.03982(13) 0.0456(6) Uani 1 1 d . . . . .
H34 H 0.7359 0.2880 -0.0070 0.055 Uiso 1 1 calc R . . . .
C35 C 0.8637(2) 0.28098(12) 0.07443(14) 0.0506(7) Uani 1 1 d . . . . .
H35 H 0.9137 0.2965 0.0511 0.061 Uiso 1 1 calc R . . . .
C36 C 0.89816(19) 0.26422(12) 0.14238(14) 0.0454(6) Uani 1 1 d . . . . .
H36 H 0.9714 0.2691 0.1655 0.054 Uiso 1 1 calc R . . . .
C37 C 0.82676(16) 0.24016(10) 0.17773(11) 0.0330(5) Uani 1 1 d . . . . .
C38B C 0.8642(5) 0.2177(3) 0.2553(3) 0.0262(11) Uani 0.729(11) 1 d . . P A 1
H38B H 0.8162 0.1811 0.2623 0.031 Uiso 0.729(11) 1 calc R . P A 1
C38A C 0.8586(17) 0.2338(8) 0.2441(10) 0.032(4) Uani 0.271(11) 1 d . U P A 2
H38A H 0.7930 0.2218 0.2587 0.039 Uiso 0.271(11) 1 calc R . P A 2
C39A C 0.8495(4) 0.2758(2) 0.2995(2) 0.0431(12) Uani 0.729(11) 1 d . . P A 1
H39D H 0.8964 0.3122 0.2937 0.065 Uiso 0.729(11) 1 calc GR . P A 1
H39E H 0.8675 0.2622 0.3475 0.065 Uiso 0.729(11) 1 calc GR . P A 1
H39F H 0.7751 0.2907 0.2857 0.065 Uiso 0.729(11) 1 calc GR . P A 1
C39B C 0.9074(15) 0.2930(5) 0.2896(6) 0.056(4) Uani 0.271(11) 1 d . . P A 2
H39A H 0.9735 0.3067 0.2786 0.084 Uiso 0.271(11) 1 calc GR . P A 2
H39B H 0.9231 0.2799 0.3377 0.084 Uiso 0.271(11) 1 calc GR . P A 2
H39C H 0.8567 0.3299 0.2813 0.084 Uiso 0.271(11) 1 calc GR . P A 2
C40A C 0.9795(4) 0.1925(3) 0.2777(2) 0.0460(11) Uani 0.729(11) 1 d . . P A 1
H40D H 0.9891 0.1564 0.2476 0.069 Uiso 0.729(11) 1 calc GR . P A 1
H40E H 0.9945 0.1763 0.3249 0.069 Uiso 0.729(11) 1 calc GR . P A 1
H40F H 1.0285 0.2287 0.2751 0.069 Uiso 0.729(11) 1 calc GR . P A 1
C40B C 0.9303(15) 0.1731(6) 0.2602(7) 0.050(4) Uani 0.271(11) 1 d . . P A 2
H40A H 0.8916 0.1342 0.2375 0.074 Uiso 0.271(11) 1 calc GR . P A 2
H40B H 0.9514 0.1658 0.3097 0.074 Uiso 0.271(11) 1 calc GR . P A 2
H40C H 0.9942 0.1802 0.2437 0.074 Uiso 0.271(11) 1 calc GR . P A 2
C41 C 0.56572(19) 0.24545(12) 0.03488(11) 0.0407(5) Uani 1 1 d . . . . .
H41 H 0.5257 0.2387 0.0704 0.049 Uiso 0.881(8) 1 calc R . P B 1
H41A H 0.5299 0.2117 0.0575 0.049 Uiso 0.119(8) 1 calc R . P B 2
C42 C 0.5194(3) 0.30812(17) -0.0052(3) 0.0657(12) Uani 0.881(8) 1 d . . P B 1
H42A H 0.5310 0.3462 0.0257 0.099 Uiso 0.881(8) 1 calc GR . P B 1
H42B H 0.4428 0.3022 -0.0252 0.099 Uiso 0.881(8) 1 calc GR . P B 1
H42C H 0.5550 0.3159 -0.0417 0.099 Uiso 0.881(8) 1 calc GR . P B 1
C42A C 0.5183(16) 0.3058(11) 0.0343(13) 0.036(5) Uani 0.119(8) 1 d . U P B 2
H42D H 0.5163 0.3176 0.0808 0.055 Uiso 0.119(8) 1 calc GR . P B 2
H42E H 0.4454 0.3039 0.0049 0.055 Uiso 0.119(8) 1 calc GR . P B 2
H42F H 0.5591 0.3392 0.0166 0.055 Uiso 0.119(8) 1 calc GR . P B 2
C43 C 0.5435(3) 0.18541(17) -0.01164(19) 0.0552(11) Uani 0.881(8) 1 d . . P B 1
H43A H 0.5805 0.1903 -0.0478 0.083 Uiso 0.881(8) 1 calc GR . P B 1
H43B H 0.4666 0.1817 -0.0321 0.083 Uiso 0.881(8) 1 calc GR . P B 1
H43C H 0.5690 0.1454 0.0150 0.083 Uiso 0.881(8) 1 calc GR . P B 1
C43A C 0.576(2) 0.2186(17) -0.0399(14) 0.061(8) Uani 0.119(8) 1 d . U P B 2
H43D H 0.6001 0.2548 -0.0644 0.091 Uiso 0.119(8) 1 calc GR . P B 2
H43E H 0.5060 0.2030 -0.0666 0.091 Uiso 0.119(8) 1 calc GR . P B 2
H43F H 0.6272 0.1821 -0.0332 0.091 Uiso 0.119(8) 1 calc GR . P B 2
C44 C 0.44295(14) 0.19153(8) 0.26430(9) 0.0204(3) Uani 1 1 d . . . . .
C45 C 0.33977(14) 0.20877(9) 0.22722(9) 0.0225(4) Uani 1 1 d . . . . .
C46 C 0.25990(15) 0.20620(9) 0.26194(10) 0.0279(4) Uani 1 1 d . . . . .
H46 H 0.1887 0.2173 0.2385 0.033 Uiso 1 1 calc R . . . .
C47 C 0.28270(16) 0.18784(10) 0.32973(11) 0.0331(5) Uani 1 1 d . . . . .
H47 H 0.2269 0.1856 0.3522 0.040 Uiso 1 1 calc R . . . .
C48 C 0.38527(17) 0.17268(10) 0.36520(10) 0.0324(4) Uani 1 1 d . . . . .
H48 H 0.3996 0.1607 0.4120 0.039 Uiso 1 1 calc R . . . .
C49 C 0.46871(15) 0.17463(9) 0.33331(10) 0.0256(4) Uani 1 1 d . . . . .
C50 C 0.58216(16) 0.15941(11) 0.37251(10) 0.0338(5) Uani 1 1 d . . . . .
H50 H 0.6300 0.1722 0.3430 0.041 Uiso 1 1 calc R . . . .
C51 C 0.6157(2) 0.20002(13) 0.43854(11) 0.0462(6) Uani 1 1 d . . . . .
H51A H 0.5997 0.2469 0.4282 0.069 Uiso 1 1 calc GR . . . .
H51B H 0.6924 0.1946 0.4587 0.069 Uiso 1 1 calc GR . . . .
H51C H 0.5764 0.1845 0.4709 0.069 Uiso 1 1 calc GR . . . .
C52 C 0.5971(2) 0.08524(12) 0.38746(13) 0.0515(6) Uani 1 1 d . . . . .
H52A H 0.5515 0.0714 0.4167 0.077 Uiso 1 1 calc GR . . . .
H52B H 0.6719 0.0764 0.4108 0.077 Uiso 1 1 calc GR . . . .
H52C H 0.5776 0.0605 0.3444 0.077 Uiso 1 1 calc GR . . . .
C53 C 0.31533(15) 0.22865(10) 0.15241(9) 0.0273(4) Uani 1 1 d . . . . .
H53 H 0.3809 0.2501 0.1449 0.033 Uiso 1 1 calc R . . . .
C54 C 0.22504(17) 0.27877(11) 0.13251(11) 0.0361(5) Uani 1 1 d . . . . .
H54A H 0.1575 0.2574 0.1332 0.054 Uiso 1 1 calc GR . . . .
H54B H 0.2207 0.2955 0.0865 0.054 Uiso 1 1 calc GR . . . .
H54C H 0.2388 0.3156 0.1651 0.054 Uiso 1 1 calc GR . . . .
C55 C 0.2921(2) 0.16765(13) 0.10654(12) 0.0512(6) Uani 1 1 d . . . . .
H55A H 0.3521 0.1367 0.1195 0.077 Uiso 1 1 calc GR . . . .
H55B H 0.2823 0.1810 0.0588 0.077 Uiso 1 1 calc GR . . . .
H55C H 0.2271 0.1461 0.1118 0.077 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
N1 P1 C5 100.67(7) . . ?
N4 P1 N1 103.78(7) . . ?
N4 P1 C5 100.84(7) . . ?
C1 N1 P1 117.99(12) . . ?
C1 N2 C2 110.23(14) . . ?
C1 N2 C17 124.79(14) . . ?
C2 N2 C17 124.60(14) . . ?
C1 N3 C3 108.49(14) . . ?
C1 N3 C4 123.09(14) . . ?
C4 N3 C3 126.77(14) . . ?
C29 N4 P1 120.90(12) . . ?
C29 N5 C30 110.45(14) . . ?
C29 N5 C44 128.02(14) . . ?
C30 N5 C44 121.52(15) . . ?
C29 N6 C31 111.03(15) . . ?
C29 N6 C32 126.15(14) . . ?
C31 N6 C32 122.82(15) . . ?
N1 C1 N2 125.29(15) . . ?
N1 C1 N3 130.22(15) . . ?
N2 C1 N3 104.46(14) . . ?
N2 C2 H2 125.8 . . ?
C3 C2 N2 108.34(15) . . ?
C3 C2 H2 125.8 . . ?
N3 C3 H3 125.9 . . ?
C2 C3 N3 108.20(15) . . ?
C2 C3 H3 125.9 . . ?
N3 C4 C5 116.06(14) . . ?
C10 C4 N3 124.43(15) . . ?
C10 C4 C5 119.46(15) . . ?
P1 C5 H5 105.1 . . ?
C4 C5 P1 110.35(11) . . ?
C4 C5 H5 105.1 . . ?
C4 C5 C6 103.70(13) . . ?
C6 C5 P1 125.86(12) . . ?
C6 C5 H5 105.1 . . ?
C5 C6 C14 122.03(15) . . ?
C7 C6 C5 115.08(16) . . ?
C7 C6 C14 122.82(16) . . ?
C6 C7 H7 117.5 . . ?
C6 C7 C8 124.90(17) . . ?
C8 C7 H7 117.5 . . ?
C7 C8 H8 116.6 . . ?
C9 C8 C7 126.74(17) . . ?
C9 C8 H8 116.6 . . ?
C8 C9 H9 116.4 . . ?
C8 C9 C10 127.29(17) . . ?
C10 C9 H9 116.4 . . ?
C4 C10 C9 119.37(16) . . ?
C4 C10 C11 123.45(15) . . ?
C9 C10 C11 117.17(15) . . ?
C10 C11 H11 107.5 . . ?
C10 C11 C12 110.29(16) . . ?
C10 C11 C13 113.09(15) . . ?
C12 C11 H11 107.5 . . ?
C13 C11 H11 107.5 . . ?
C13 C11 C12 110.74(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C14 H14 108.0 . . ?
C6 C14 C15 110.51(16) . . ?
C6 C14 C16 111.59(16) . . ?
C15 C14 H14 108.0 . . ?
C16 C14 H14 108.0 . . ?
C16 C14 C15 110.59(16) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N2 119.23(16) . . ?
C18 C17 C22 122.97(17) . . ?
C22 C17 N2 117.79(16) . . ?
C17 C18 C19 116.95(19) . . ?
C17 C18 C26 121.44(17) . . ?
C19 C18 C26 121.59(18) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.2(2) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.72(19) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.7(2) . . ?
C22 C21 H21 119.6 . . ?
C17 C22 C23 120.90(16) . . ?
C21 C22 C17 117.43(18) . . ?
C21 C22 C23 121.62(17) . . ?
C22 C23 H23 107.3 . . ?
C22 C23 C24 114.10(16) . . ?
C22 C23 C25 110.46(16) . . ?
C24 C23 H23 107.3 . . ?
C24 C23 C25 109.96(17) . . ?
C25 C23 H23 107.3 . . ?
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 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 C26 H26 107.7 . . ?
C18 C26 C27 112.15(19) . . ?
C18 C26 C28 110.62(18) . . ?
C27 C26 H26 107.7 . . ?
C28 C26 H26 107.7 . . ?
C28 C26 C27 110.88(18) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N4 C29 N5 133.18(16) . . ?
N4 C29 N6 123.46(15) . . ?
N5 C29 N6 103.35(14) . . ?
N5 C30 H30 126.0 . . ?
C31 C30 N5 107.97(16) . . ?
C31 C30 H30 126.0 . . ?
N6 C31 H31 126.4 . . ?
C30 C31 N6 107.16(16) . . ?
C30 C31 H31 126.4 . . ?
C33 C32 N6 118.02(17) . . ?
C33 C32 C37 123.46(18) . . ?
C37 C32 N6 118.34(18) . . ?
C32 C33 C34 117.0(2) . . ?
C32 C33 C41 121.55(18) . . ?
C34 C33 C41 121.4(2) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 C33 120.8(2) . . ?
C35 C34 H34 119.6 . . ?
C34 C35 H35 119.5 . . ?
C34 C35 C36 121.0(2) . . ?
C36 C35 H35 119.5 . . ?
C35 C36 H36 119.6 . . ?
C35 C36 C37 120.8(2) . . ?
C37 C36 H36 119.6 . . ?
C32 C37 C38B 120.8(3) . . ?
C36 C37 C32 116.9(2) . . ?
C36 C37 C38B 122.2(3) . . ?
C38A C37 C32 123.1(9) . . ?
C38A C37 C36 119.1(9) . . ?
C37 C38B H38B 108.0 . . ?
C39A C38B C37 108.0(4) . . ?
C39A C38B H38B 108.0 . . ?
C39A C38B C40A 110.1(4) . . ?
C40A C38B C37 114.5(5) . . ?
C40A C38B H38B 108.0 . . ?
C37 C38A H38A 105.2 . . ?
C37 C38A C39B 120.7(12) . . ?
C37 C38A C40B 108.2(15) . . ?
C39B C38A H38A 105.2 . . ?
C40B C38A H38A 105.2 . . ?
C40B C38A C39B 111.2(13) . . ?
C38B C39A H39D 109.5 . . ?
C38B C39A H39E 109.5 . . ?
C38B C39A H39F 109.5 . . ?
H39D C39A H39E 109.5 . . ?
H39D C39A H39F 109.5 . . ?
H39E C39A H39F 109.5 . . ?
C38A C39B H39A 109.5 . . ?
C38A C39B H39B 109.5 . . ?
C38A C39B H39C 109.5 . . ?
H39A C39B H39B 109.5 . . ?
H39A C39B H39C 109.5 . . ?
H39B C39B H39C 109.5 . . ?
C38B C40A H40D 109.5 . . ?
C38B C40A H40E 109.5 . . ?
C38B C40A H40F 109.5 . . ?
H40D C40A H40E 109.5 . . ?
H40D C40A H40F 109.5 . . ?
H40E C40A H40F 109.5 . . ?
C38A C40B H40A 109.5 . . ?
C38A C40B H40B 109.5 . . ?
C38A C40B H40C 109.5 . . ?
H40A C40B H40B 109.5 . . ?
H40A C40B H40C 109.5 . . ?
H40B C40B H40C 109.5 . . ?
C33 C41 H41 106.7 . . ?
C33 C41 H41A 110.7 . . ?
C33 C41 C42 113.2(2) . . ?
C33 C41 C43A 100.7(10) . . ?
C42 C41 H41 106.7 . . ?
C42A C41 C33 108.3(10) . . ?
C42A C41 H41A 110.7 . . ?
C42A C41 C43A 115.4(13) . . ?
C43 C41 C33 112.9(2) . . ?
C43 C41 H41 106.7 . . ?
C43 C41 C42 110.1(2) . . ?
C43A C41 H41A 110.7 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C42A H42D 109.5 . . ?
C41 C42A H42E 109.5 . . ?
C41 C42A H42F 109.5 . . ?
H42D C42A H42E 109.5 . . ?
H42D C42A H42F 109.5 . . ?
H42E C42A H42F 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C41 C43A H43D 109.5 . . ?
C41 C43A H43E 109.5 . . ?
C41 C43A H43F 109.5 . . ?
H43D C43A H43E 109.5 . . ?
H43D C43A H43F 109.5 . . ?
H43E C43A H43F 109.5 . . ?
C45 C44 N5 118.68(15) . . ?
C49 C44 N5 117.93(16) . . ?
C49 C44 C45 123.24(16) . . ?
C44 C45 C53 121.70(16) . . ?
C46 C45 C44 116.88(17) . . ?
C46 C45 C53 121.42(16) . . ?
C45 C46 H46 119.5 . . ?
C47 C46 C45 121.04(18) . . ?
C47 C46 H46 119.5 . . ?
C46 C47 H47 119.6 . . ?
C48 C47 C46 120.72(18) . . ?
C48 C47 H47 119.6 . . ?
C47 C48 H48 119.6 . . ?
C47 C48 C49 120.90(18) . . ?
C49 C48 H48 119.6 . . ?
C44 C49 C48 117.19(17) . . ?
C44 C49 C50 121.70(17) . . ?
C48 C49 C50 121.11(17) . . ?
C49 C50 H50 107.7 . . ?
C49 C50 C51 111.58(18) . . ?
C49 C50 C52 111.06(18) . . ?
C51 C50 H50 107.7 . . ?
C52 C50 H50 107.7 . . ?
C52 C50 C51 110.98(18) . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C50 C52 H52A 109.5 . . ?
C50 C52 H52B 109.5 . . ?
C50 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C45 C53 H53 107.4 . . ?
C45 C53 C54 112.84(16) . . ?
C45 C53 C55 110.58(17) . . ?
C54 C53 H53 107.4 . . ?
C54 C53 C55 111.00(17) . . ?
C55 C53 H53 107.4 . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C53 C55 H55A 109.5 . . ?
C53 C55 H55B 109.5 . . ?
C53 C55 H55C 109.5 . . ?
H55A C55 H55B 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 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 N1 1.7016(15) . ?
P1 N4 1.6932(15) . ?
P1 C5 1.8659(17) . ?
N1 C1 1.282(2) . ?
N2 C1 1.385(2) . ?
N2 C2 1.391(2) . ?
N2 C17 1.433(2) . ?
N3 C1 1.407(2) . ?
N3 C3 1.413(2) . ?
N3 C4 1.412(2) . ?
N4 C29 1.294(2) . ?
N5 C29 1.384(2) . ?
N5 C30 1.395(2) . ?
N5 C44 1.440(2) . ?
N6 C29 1.384(2) . ?
N6 C31 1.393(2) . ?
N6 C32 1.438(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.327(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.510(2) . ?
C4 C10 1.366(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.510(2) . ?
C6 C7 1.358(2) . ?
C6 C14 1.517(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.433(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.366(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.438(2) . ?
C10 C11 1.526(2) . ?
C11 H11 1.0000 . ?
C11 C12 1.531(3) . ?
C11 C13 1.529(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 1.0000 . ?
C14 C15 1.531(3) . ?
C14 C16 1.523(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.395(3) . ?
C17 C22 1.405(3) . ?
C18 C19 1.396(3) . ?
C18 C26 1.516(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.378(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.391(3) . ?
C22 C23 1.521(3) . ?
C23 H23 1.0000 . ?
C23 C24 1.523(3) . ?
C23 C25 1.527(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26 1.0000 . ?
C26 C27 1.528(3) . ?
C26 C28 1.525(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C30 H30 0.9500 . ?
C30 C31 1.330(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.392(3) . ?
C32 C37 1.398(3) . ?
C33 C34 1.398(3) . ?
C33 C41 1.520(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.374(4) . ?
C35 H35 0.9500 . ?
C35 C36 1.375(4) . ?
C36 H36 0.9500 . ?
C36 C37 1.396(3) . ?
C37 C38B 1.587(7) . ?
C37 C38A 1.308(19) . ?
C38B H38B 1.0000 . ?
C38B C39A 1.519(7) . ?
C38B C40A 1.534(7) . ?
C38A H38A 1.0000 . ?
C38A C39B 1.54(2) . ?
C38A C40B 1.523(19) . ?
C39A H39D 0.9800 . ?
C39A H39E 0.9800 . ?
C39A H39F 0.9800 . ?
C39B H39A 0.9800 . ?
C39B H39B 0.9800 . ?
C39B H39C 0.9800 . ?
C40A H40D 0.9800 . ?
C40A H40E 0.9800 . ?
C40A H40F 0.9800 . ?
C40B H40A 0.9800 . ?
C40B H40B 0.9800 . ?
C40B H40C 0.9800 . ?
C41 H41 1.0000 . ?
C41 H41A 1.0000 . ?
C41 C42 1.540(4) . ?
C41 C42A 1.36(2) . ?
C41 C43 1.517(4) . ?
C41 C43A 1.65(3) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C42A H42D 0.9800 . ?
C42A H42E 0.9800 . ?
C42A H42F 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C43A H43D 0.9800 . ?
C43A H43E 0.9800 . ?
C43A H43F 0.9800 . ?
C44 C45 1.400(2) . ?
C44 C49 1.394(3) . ?
C45 C46 1.396(3) . ?
C45 C53 1.520(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.379(3) . ?
C47 H47 0.9500 . ?
C47 C48 1.374(3) . ?
C48 H48 0.9500 . ?
C48 C49 1.397(3) . ?
C49 C50 1.513(3) . ?
C50 H50 1.0000 . ?
C50 C51 1.534(3) . ?
C50 C52 1.531(3) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53 1.0000 . ?
C53 C54 1.522(3) . ?
C53 C55 1.526(3) . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
