#------------------------------------------------------------------------------
#$Date: 2022-06-16 00:55:07 +0300 (Thu, 16 Jun 2022) $
#$Revision: 276051 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/02/7130233.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_7130233
loop_
_publ_author_name
'Dettling, Lea'
'Papke, Martin'
'Sklorz, Julian'
'Buzsaki, Daniel'
'Kelemen, Zsolt'
'Weber, Manuela'
'Nyulaszi, Laszlo'
'Muller, Christian'
_publ_section_title
;
 A New Access to Diazaphospholes via Cycloaddition-Cycloreversion
 Reactions on Triazaphospholes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02269A
_journal_year                    2022
_chemical_formula_sum            'C22 H26 N3 O5 P W'
_chemical_formula_weight         627.28
_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   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-05-30 deposited with the CCDC.	2022-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                112.5214(6)
_cell_angle_beta                 102.9855(5)
_cell_angle_gamma                91.3575(5)
_cell_formula_units_Z            4
_cell_length_a                   11.1075(2)
_cell_length_b                   14.6470(2)
_cell_length_c                   16.9008(3)
_cell_measurement_reflns_used    9661
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.40
_cell_volume                     2456.50(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            68480
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         1.896
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    4.804
_exptl_absorpt_correction_T_max  0.4010
_exptl_absorpt_correction_T_min  0.2195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1252 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.5474.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.090
_exptl_transmission_factor_max   0.4010
_exptl_transmission_factor_min   0.2195
_refine_diff_density_max         1.151
_refine_diff_density_min         -1.221
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         12174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0192
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0125P)²+1.6662P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0440
_refine_ls_wR_factor_ref         0.0452
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11237
_reflns_number_total             12174
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02269a2.cif
_cod_data_source_block           LD1209
_cod_database_code               7130233
_shelx_shelxl_version_number     2018/3
_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_min   0.250
_shelx_estimated_absorpt_t_max   0.672
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
W1 W 0.47619(2) 0.69029(2) 0.14882(2) 0.01778(3) Uani 1 1 d . . . . .
P1 P 0.38485(5) 0.71329(4) 0.27340(3) 0.01369(10) Uani 1 1 d . . . . .
O1 O 0.69454(19) 0.85319(16) 0.29445(14) 0.0439(5) Uani 1 1 d . . . . .
O2 O 0.3278(2) 0.84870(15) 0.09229(13) 0.0413(5) Uani 1 1 d . . . . .
O3 O 0.6058(2) 0.67284(16) -0.00300(15) 0.0494(6) Uani 1 1 d . . . . .
O4 O 0.26357(18) 0.51938(15) 0.00889(13) 0.0378(4) Uani 1 1 d . . . . .
O5 O 0.6228(2) 0.51304(16) 0.16697(14) 0.0448(5) Uani 1 1 d . . . . .
N1 N 0.27698(15) 0.78786(12) 0.30406(11) 0.0133(3) Uani 1 1 d . . . . .
N2 N 0.25121(17) 0.79379(14) 0.38060(12) 0.0186(4) Uani 1 1 d . . . . .
N3 N 0.31866(17) 0.73912(14) 0.41370(12) 0.0190(4) Uani 1 1 d . . . . .
C1 C 0.39858(19) 0.69022(15) 0.36675(13) 0.0147(4) Uani 1 1 d . . . . .
C2 C 0.21711(19) 0.85122(15) 0.26332(13) 0.0138(4) Uani 1 1 d . . . . .
C3 C 0.27489(19) 0.94834(15) 0.29141(14) 0.0163(4) Uani 1 1 d . . . . .
C4 C 0.2159(2) 1.00821(16) 0.25112(15) 0.0195(4) Uani 1 1 d . . . . .
H4 H 0.252319 1.074509 0.268508 0.023 Uiso 1 1 calc R U . . .
C5 C 0.1053(2) 0.97251(16) 0.18632(15) 0.0207(4) Uani 1 1 d . . . . .
H5 H 0.067112 1.014074 0.159040 0.025 Uiso 1 1 calc R U . . .
C6 C 0.0496(2) 0.87644(16) 0.16082(14) 0.0196(4) Uani 1 1 d . . . . .
H6 H -0.026945 0.853110 0.116655 0.024 Uiso 1 1 calc R U . . .
C7 C 0.10430(19) 0.81390(15) 0.19902(14) 0.0161(4) Uani 1 1 d . . . . .
C8 C 0.3946(2) 0.98988(16) 0.36439(16) 0.0226(5) Uani 1 1 d . . . . .
H8 H 0.434477 0.932473 0.372457 0.027 Uiso 1 1 calc R U . . .
C9 C 0.4874(3) 1.0488(2) 0.3419(2) 0.0387(7) Uani 1 1 d . . . . .
H9A H 0.501496 1.007801 0.284220 0.058 Uiso 1 1 calc R U . . .
H9B H 0.566381 1.067004 0.387438 0.058 Uiso 1 1 calc R U . . .
H9C H 0.453925 1.109303 0.339725 0.058 Uiso 1 1 calc R U . . .
C10 C 0.3636(3) 1.05398(19) 0.45120(17) 0.0339(6) Uani 1 1 d . . . . .
H10A H 0.318397 1.107884 0.443515 0.051 Uiso 1 1 calc R U . . .
H10B H 0.440844 1.082400 0.497979 0.051 Uiso 1 1 calc R U . . .
H10C H 0.311722 1.012737 0.467738 0.051 Uiso 1 1 calc R U . . .
C11 C 0.0400(2) 0.70986(16) 0.17158(15) 0.0201(4) Uani 1 1 d . . . . .
H11 H 0.099121 0.672973 0.198415 0.024 Uiso 1 1 calc R U . . .
C12 C 0.0063(3) 0.65284(19) 0.07185(17) 0.0329(6) Uani 1 1 d . . . . .
H12A H -0.058371 0.683659 0.044400 0.049 Uiso 1 1 calc R U . . .
H12B H -0.024890 0.583616 0.057041 0.049 Uiso 1 1 calc R U . . .
H12C H 0.080252 0.654412 0.049692 0.049 Uiso 1 1 calc R U . . .
C13 C -0.0756(3) 0.7148(2) 0.2074(2) 0.0377(6) Uani 1 1 d . . . . .
H13A H -0.134629 0.751453 0.182567 0.057 Uiso 1 1 calc R U . . .
H13B H -0.051363 0.748883 0.272060 0.057 Uiso 1 1 calc R U . . .
H13C H -0.114814 0.647084 0.190413 0.057 Uiso 1 1 calc R U . . .
C14 C 0.4846(2) 0.62601(15) 0.39980(14) 0.0174(4) Uani 1 1 d . . . . .
C15 C 0.4426(2) 0.51583(16) 0.33918(16) 0.0258(5) Uani 1 1 d . . . . .
H15A H 0.442141 0.505128 0.278211 0.039 Uiso 1 1 calc R U . . .
H15B H 0.358554 0.497274 0.341639 0.039 Uiso 1 1 calc R U . . .
H15C H 0.500171 0.474713 0.358974 0.039 Uiso 1 1 calc R U . . .
C16 C 0.4820(2) 0.64336(18) 0.49458(15) 0.0262(5) Uani 1 1 d . . . . .
H16A H 0.397300 0.624999 0.495849 0.039 Uiso 1 1 calc R U . . .
H16B H 0.508536 0.713795 0.533189 0.039 Uiso 1 1 calc R U . . .
H16C H 0.538701 0.602385 0.515425 0.039 Uiso 1 1 calc R U . . .
C17 C 0.6180(2) 0.65398(18) 0.39942(16) 0.0240(5) Uani 1 1 d . . . . .
H17A H 0.621661 0.641738 0.338837 0.036 Uiso 1 1 calc R U . . .
H17B H 0.673673 0.613479 0.421761 0.036 Uiso 1 1 calc R U . . .
H17C H 0.644224 0.724619 0.437422 0.036 Uiso 1 1 calc R U . . .
C18 C 0.6172(2) 0.79591(19) 0.24122(18) 0.0292(5) Uani 1 1 d . . . . .
C19 C 0.3797(2) 0.79452(19) 0.11691(16) 0.0274(5) Uani 1 1 d . . . . .
C20 C 0.5592(3) 0.67940(19) 0.05238(18) 0.0306(6) Uani 1 1 d . . . . .
C21 C 0.3377(2) 0.58188(18) 0.05968(15) 0.0237(5) Uani 1 1 d . . . . .
C22 C 0.5705(2) 0.57796(19) 0.16362(16) 0.0273(5) Uani 1 1 d . . . . .
W1B W 0.76535(2) 0.17700(2) 0.16632(2) 0.01653(3) Uani 1 1 d . . . . .
P1B P 0.95569(5) 0.21210(4) 0.28371(3) 0.01324(10) Uani 1 1 d . . . . .
O1B O 0.91194(17) 0.07696(14) 0.02002(12) 0.0311(4) Uani 1 1 d . . . . .
O2B O 0.81014(19) 0.36284(14) 0.11789(13) 0.0382(5) Uani 1 1 d . . . . .
O3B O 0.50855(17) 0.12375(17) 0.02345(13) 0.0411(5) Uani 1 1 d . . . . .
O4B O 0.64391(18) 0.30339(17) 0.32258(13) 0.0444(5) Uani 1 1 d . . . . .
O5B O 0.6995(2) -0.03454(16) 0.16798(14) 0.0504(6) Uani 1 1 d . . . . .
N1B N 1.08982(15) 0.27948(13) 0.29938(11) 0.0139(3) Uani 1 1 d . . . . .
N2B N 1.17996(17) 0.28601(14) 0.37155(12) 0.0190(4) Uani 1 1 d . . . . .
N3B N 1.14016(17) 0.23631(14) 0.41211(12) 0.0190(4) Uani 1 1 d . . . . .
C01A C 1.16761(18) 0.31031(15) 0.18566(14) 0.0149(4) Uani 1 1 d . . . . .
C1B C 1.02104(19) 0.19123(15) 0.37624(13) 0.0146(4) Uani 1 1 d . . . . .
C2B C 1.11033(18) 0.34421(15) 0.25581(14) 0.0149(4) Uani 1 1 d . . . . .
C4B C 1.1825(2) 0.37464(16) 0.14461(14) 0.0178(4) Uani 1 1 d . . . . .
H4B H 1.220780 0.354243 0.096629 0.021 Uiso 1 1 calc R U . . .
C5B C 1.1424(2) 0.46796(17) 0.17283(15) 0.0215(4) Uani 1 1 d . . . . .
H5B H 1.151500 0.510220 0.143161 0.026 Uiso 1 1 calc R U . . .
C6B C 1.0891(2) 0.50003(16) 0.24388(16) 0.0218(5) Uani 1 1 d . . . . .
H6B H 1.063805 0.564823 0.263301 0.026 Uiso 1 1 calc R U . . .
C7B C 1.0719(2) 0.43886(16) 0.28744(15) 0.0194(4) Uani 1 1 d . . . . .
C8B C 1.2219(2) 0.21214(16) 0.16031(15) 0.0189(4) Uani 1 1 d . . . . .
H8B H 1.173228 0.166110 0.175956 0.023 Uiso 1 1 calc R U . . .
C9B C 1.3569(2) 0.22929(19) 0.21487(17) 0.0278(5) Uani 1 1 d . . . . .
H9BA H 1.390800 0.165408 0.201289 0.042 Uiso 1 1 calc R U . . .
H9BB H 1.359719 0.259681 0.278071 0.042 Uiso 1 1 calc R U . . .
H9BC H 1.406726 0.273740 0.200148 0.042 Uiso 1 1 calc R U . . .
C10B C 1.2161(2) 0.16186(18) 0.06203(16) 0.0270(5) Uani 1 1 d . . . . .
H10D H 1.129648 0.152112 0.027497 0.041 Uiso 1 1 calc R U . . .
H10E H 1.247549 0.097158 0.049463 0.041 Uiso 1 1 calc R U . . .
H10F H 1.267279 0.203954 0.045871 0.041 Uiso 1 1 calc R U . . .
C11B C 1.0211(2) 0.47815(16) 0.36889(16) 0.0235(5) Uani 1 1 d . . . . .
H11B H 1.000806 0.420277 0.383170 0.028 Uiso 1 1 calc R U . . .
C12B C 0.9018(3) 0.5261(2) 0.3545(2) 0.0372(6) Uani 1 1 d . . . . .
H12D H 0.918089 0.581743 0.338258 0.056 Uiso 1 1 calc R U . . .
H12E H 0.873882 0.550676 0.409268 0.056 Uiso 1 1 calc R U . . .
H12F H 0.836975 0.476542 0.306908 0.056 Uiso 1 1 calc R U . . .
C13B C 1.1217(3) 0.5504(2) 0.44746(17) 0.0344(6) Uani 1 1 d . . . . .
H13D H 1.193183 0.515453 0.459503 0.052 Uiso 1 1 calc R U . . .
H13E H 1.088253 0.576545 0.499743 0.052 Uiso 1 1 calc R U . . .
H13F H 1.148207 0.605596 0.433571 0.052 Uiso 1 1 calc R U . . .
C14B C 0.9648(2) 0.13405(15) 0.42031(14) 0.0166(4) Uani 1 1 d . . . . .
C15B C 0.8276(2) 0.14881(18) 0.41403(16) 0.0229(5) Uani 1 1 d . . . . .
H15D H 0.780989 0.121219 0.351691 0.034 Uiso 1 1 calc R U . . .
H15E H 0.820201 0.220081 0.440861 0.034 Uiso 1 1 calc R U . . .
H15F H 0.793837 0.114597 0.445516 0.034 Uiso 1 1 calc R U . . .
C16B C 1.0341(2) 0.1725(2) 0.51829(16) 0.0297(5) Uani 1 1 d . . . . .
H16D H 1.120912 0.159031 0.523512 0.045 Uiso 1 1 calc R U . . .
H16E H 0.994280 0.138702 0.547526 0.045 Uiso 1 1 calc R U . . .
H16F H 1.031516 0.244412 0.546546 0.045 Uiso 1 1 calc R U . . .
C17B C 0.9747(2) 0.02300(17) 0.37410(17) 0.0274(5) Uani 1 1 d . . . . .
H17D H 0.928408 -0.001325 0.311804 0.041 Uiso 1 1 calc R U . . .
H17E H 0.939611 -0.013733 0.403141 0.041 Uiso 1 1 calc R U . . .
H17F H 1.062344 0.012949 0.377764 0.041 Uiso 1 1 calc R U . . .
C18B C 0.8583(2) 0.11012(16) 0.07211(15) 0.0201(4) Uani 1 1 d . . . . .
C19B C 0.7972(2) 0.30043(18) 0.14076(16) 0.0254(5) Uani 1 1 d . . . . .
C20B C 0.6016(2) 0.1435(2) 0.07465(16) 0.0283(5) Uani 1 1 d . . . . .
C21B C 0.6837(2) 0.2562(2) 0.26549(16) 0.0283(5) Uani 1 1 d . . . . .
C22B C 0.7246(2) 0.0428(2) 0.17084(16) 0.0291(5) 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 0.0033 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'
O O 0.0106 0.0060 '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'
W W -0.8490 6.8722 '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
C20 W1 C22 87.47(10) . . ?
C20 W1 C21 90.20(10) . . ?
C22 W1 C21 86.58(10) . . ?
C20 W1 C19 86.51(10) . . ?
C22 W1 C19 172.66(9) . . ?
C21 W1 C19 89.25(10) . . ?
C20 W1 C18 90.89(11) . . ?
C22 W1 C18 91.52(10) . . ?
C21 W1 C18 177.76(9) . . ?
C19 W1 C18 92.77(10) . . ?
C20 W1 P1 176.17(8) . . ?
C22 W1 P1 93.24(7) . . ?
C21 W1 P1 93.60(6) . . ?
C19 W1 P1 93.04(6) . . ?
C18 W1 P1 85.33(7) . . ?
N1 P1 C1 88.67(9) . . ?
N1 P1 W1 126.61(6) . . ?
C1 P1 W1 144.14(7) . . ?
N2 N1 C2 117.28(16) . . ?
N2 N1 P1 114.45(13) . . ?
C2 N1 P1 128.07(14) . . ?
N3 N2 N1 110.82(16) . . ?
N2 N3 C1 115.31(17) . . ?
N3 C1 C14 120.26(18) . . ?
N3 C1 P1 110.73(15) . . ?
C14 C1 P1 129.01(16) . . ?
C7 C2 C3 122.98(18) . . ?
C7 C2 N1 119.01(18) . . ?
C3 C2 N1 118.00(18) . . ?
C4 C3 C2 117.15(19) . . ?
C4 C3 C8 120.20(19) . . ?
C2 C3 C8 122.63(18) . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C2 117.57(19) . . ?
C6 C7 C11 119.86(19) . . ?
C2 C7 C11 122.56(18) . . ?
C3 C8 C9 112.6(2) . . ?
C3 C8 C10 109.34(19) . . ?
C9 C8 C10 110.9(2) . . ?
C3 C8 H8 107.9 . . ?
C9 C8 H8 107.9 . . ?
C10 C8 H8 107.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C7 111.71(19) . . ?
C12 C11 C13 110.7(2) . . ?
C7 C11 C13 110.46(19) . . ?
C12 C11 H11 108.0 . . ?
C7 C11 H11 108.0 . . ?
C13 C11 H11 108.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 C16 110.24(18) . . ?
C1 C14 C17 109.47(17) . . ?
C16 C14 C17 108.44(19) . . ?
C1 C14 C15 109.54(18) . . ?
C16 C14 C15 109.53(19) . . ?
C17 C14 C15 109.59(19) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C18 W1 177.6(2) . . ?
O2 C19 W1 174.3(2) . . ?
O3 C20 W1 179.5(3) . . ?
O4 C21 W1 177.6(2) . . ?
O5 C22 W1 176.2(2) . . ?
C20B W1B C18B 91.86(9) . . ?
C20B W1B C22B 85.82(10) . . ?
C18B W1B C22B 89.66(10) . . ?
C20B W1B C19B 87.78(10) . . ?
C18B W1B C19B 84.33(9) . . ?
C22B W1B C19B 171.08(10) . . ?
C20B W1B C21B 91.43(10) . . ?
C18B W1B C21B 174.55(9) . . ?
C22B W1B C21B 94.91(11) . . ?
C19B W1B C21B 91.46(10) . . ?
C20B W1B P1B 175.53(7) . . ?
C18B W1B P1B 91.02(6) . . ?
C22B W1B P1B 90.78(7) . . ?
C19B W1B P1B 95.91(7) . . ?
C21B W1B P1B 85.96(6) . . ?
N1B P1B C1B 88.79(9) . . ?
N1B P1B W1B 128.04(6) . . ?
C1B P1B W1B 143.17(7) . . ?
N2B N1B C2B 117.66(16) . . ?
N2B N1B P1B 114.37(13) . . ?
C2B N1B P1B 126.86(14) . . ?
N3B N2B N1B 110.57(17) . . ?
N2B N3B C1B 115.71(17) . . ?
C4B C01A C2B 117.06(19) . . ?
C4B C01A C8B 120.83(19) . . ?
C2B C01A C8B 121.89(18) . . ?
N3B C1B C14B 119.68(18) . . ?
N3B C1B P1B 110.55(15) . . ?
C14B C1B P1B 129.76(15) . . ?
C7B C2B C01A 123.46(18) . . ?
C7B C2B N1B 117.21(18) . . ?
C01A C2B N1B 119.33(18) . . ?
C5B C4B C01A 120.9(2) . . ?
C5B C4B H4B 119.6 . . ?
C01A C4B H4B 119.6 . . ?
C6B C5B C4B 120.5(2) . . ?
C6B C5B H5B 119.8 . . ?
C4B C5B H5B 119.8 . . ?
C5B C6B C7B 121.1(2) . . ?
C5B C6B H6B 119.5 . . ?
C7B C6B H6B 119.5 . . ?
C6B C7B C2B 117.0(2) . . ?
C6B C7B C11B 120.05(19) . . ?
C2B C7B C11B 122.85(19) . . ?
C01A C8B C10B 113.57(18) . . ?
C01A C8B C9B 109.20(18) . . ?
C10B C8B C9B 109.89(19) . . ?
C01A C8B H8B 108.0 . . ?
C10B C8B H8B 108.0 . . ?
C9B C8B H8B 108.0 . . ?
C8B C9B H9BA 109.5 . . ?
C8B C9B H9BB 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
C8B C9B H9BC 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
C8B C10B H10D 109.5 . . ?
C8B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C8B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C7B C11B C13B 109.63(19) . . ?
C7B C11B C12B 113.0(2) . . ?
C13B C11B C12B 111.3(2) . . ?
C7B C11B H11B 107.6 . . ?
C13B C11B H11B 107.6 . . ?
C12B C11B H11B 107.6 . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C11B C13B H13D 109.5 . . ?
C11B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C11B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C1B C14B C15B 110.37(17) . . ?
C1B C14B C17B 109.49(17) . . ?
C15B C14B C17B 108.99(18) . . ?
C1B C14B C16B 109.55(18) . . ?
C15B C14B C16B 108.41(19) . . ?
C17B C14B C16B 110.03(19) . . ?
C14B C15B H15D 109.5 . . ?
C14B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C14B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C14B C16B H16D 109.5 . . ?
C14B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C14B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C14B C17B H17D 109.5 . . ?
C14B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C14B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
O1B C18B W1B 177.0(2) . . ?
O2B C19B W1B 173.1(2) . . ?
O3B C20B W1B 179.0(2) . . ?
O4B C21B W1B 176.5(2) . . ?
O5B C22B W1B 175.9(2) . . ?
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
W1 C20 2.004(2) . ?
W1 C22 2.036(2) . ?
W1 C21 2.041(3) . ?
W1 C19 2.054(2) . ?
W1 C18 2.055(3) . ?
W1 P1 2.4512(5) . ?
P1 N1 1.6747(17) . ?
P1 C1 1.712(2) . ?
O1 C18 1.136(3) . ?
O2 C19 1.141(3) . ?
O3 C20 1.142(3) . ?
O4 C21 1.139(3) . ?
O5 C22 1.139(3) . ?
N1 N2 1.358(2) . ?
N1 C2 1.446(2) . ?
N2 N3 1.303(2) . ?
N3 C1 1.357(3) . ?
C1 C14 1.521(3) . ?
C2 C7 1.397(3) . ?
C2 C3 1.401(3) . ?
C3 C4 1.395(3) . ?
C3 C8 1.520(3) . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(3) . ?
C6 H6 0.9500 . ?
C7 C11 1.519(3) . ?
C8 C9 1.528(4) . ?
C8 C10 1.530(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.517(3) . ?
C11 C13 1.529(3) . ?
C11 H11 1.0000 . ?
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 C16 1.530(3) . ?
C14 C17 1.531(3) . ?
C14 C15 1.534(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 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
W1B C20B 2.015(2) . ?
W1B C18B 2.038(2) . ?
W1B C22B 2.040(3) . ?
W1B C19B 2.054(2) . ?
W1B C21B 2.055(3) . ?
W1B P1B 2.4398(5) . ?
P1B N1B 1.6783(17) . ?
P1B C1B 1.713(2) . ?
O1B C18B 1.135(3) . ?
O2B C19B 1.138(3) . ?
O3B C20B 1.137(3) . ?
O4B C21B 1.139(3) . ?
O5B C22B 1.140(3) . ?
N1B N2B 1.363(2) . ?
N1B C2B 1.447(2) . ?
N2B N3B 1.303(2) . ?
N3B C1B 1.359(3) . ?
C01A C4B 1.393(3) . ?
C01A C2B 1.400(3) . ?
C01A C8B 1.517(3) . ?
C1B C14B 1.519(3) . ?
C2B C7B 1.398(3) . ?
C4B C5B 1.386(3) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.383(3) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.393(3) . ?
C6B H6B 0.9500 . ?
C7B C11B 1.517(3) . ?
C8B C10B 1.522(3) . ?
C8B C9B 1.532(3) . ?
C8B H8B 1.0000 . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11B C13B 1.527(4) . ?
C11B C12B 1.529(4) . ?
C11B H11B 1.0000 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14B C15B 1.530(3) . ?
C14B C17B 1.530(3) . ?
C14B C16B 1.531(3) . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 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
C1 P1 N1 N2 -0.93(15) . . . . ?
W1 P1 N1 N2 -174.00(11) . . . . ?
C1 P1 N1 C2 173.70(18) . . . . ?
W1 P1 N1 C2 0.6(2) . . . . ?
C2 N1 N2 N3 -174.85(18) . . . . ?
P1 N1 N2 N3 0.4(2) . . . . ?
N1 N2 N3 C1 0.6(3) . . . . ?
N2 N3 C1 C14 178.52(18) . . . . ?
N2 N3 C1 P1 -1.3(2) . . . . ?
N1 P1 C1 N3 1.20(16) . . . . ?
W1 P1 C1 N3 171.69(10) . . . . ?
N1 P1 C1 C14 -178.6(2) . . . . ?
W1 P1 C1 C14 -8.1(3) . . . . ?
N2 N1 C2 C7 -92.8(2) . . . . ?
P1 N1 C2 C7 92.7(2) . . . . ?
N2 N1 C2 C3 86.3(2) . . . . ?
P1 N1 C2 C3 -88.1(2) . . . . ?
C7 C2 C3 C4 -1.0(3) . . . . ?
N1 C2 C3 C4 179.80(18) . . . . ?
C7 C2 C3 C8 177.1(2) . . . . ?
N1 C2 C3 C8 -2.0(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C8 C3 C4 C5 -178.3(2) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
C5 C6 C7 C11 178.5(2) . . . . ?
C3 C2 C7 C6 1.2(3) . . . . ?
N1 C2 C7 C6 -179.63(18) . . . . ?
C3 C2 C7 C11 -177.6(2) . . . . ?
N1 C2 C7 C11 1.6(3) . . . . ?
C4 C3 C8 C9 -45.2(3) . . . . ?
C2 C3 C8 C9 136.7(2) . . . . ?
C4 C3 C8 C10 78.6(3) . . . . ?
C2 C3 C8 C10 -99.5(2) . . . . ?
C6 C7 C11 C12 52.4(3) . . . . ?
C2 C7 C11 C12 -128.8(2) . . . . ?
C6 C7 C11 C13 -71.2(3) . . . . ?
C2 C7 C11 C13 107.6(2) . . . . ?
N3 C1 C14 C16 -10.6(3) . . . . ?
P1 C1 C14 C16 169.14(17) . . . . ?
N3 C1 C14 C17 -129.8(2) . . . . ?
P1 C1 C14 C17 49.9(3) . . . . ?
N3 C1 C14 C15 110.0(2) . . . . ?
P1 C1 C14 C15 -70.3(2) . . . . ?
C1B P1B N1B N2B -0.11(16) . . . . ?
W1B P1B N1B N2B 179.79(11) . . . . ?
C1B P1B N1B C2B -167.69(18) . . . . ?
W1B P1B N1B C2B 12.2(2) . . . . ?
C2B N1B N2B N3B 169.39(18) . . . . ?
P1B N1B N2B N3B 0.6(2) . . . . ?
N1B N2B N3B C1B -0.9(3) . . . . ?
N2B N3B C1B C14B -178.19(18) . . . . ?
N2B N3B C1B P1B 0.8(2) . . . . ?
N1B P1B C1B N3B -0.38(16) . . . . ?
W1B P1B C1B N3B 179.74(10) . . . . ?
N1B P1B C1B C14B 178.5(2) . . . . ?
W1B P1B C1B C14B -1.4(3) . . . . ?
C4B C01A C2B C7B -2.0(3) . . . . ?
C8B C01A C2B C7B 172.6(2) . . . . ?
C4B C01A C2B N1B 178.53(18) . . . . ?
C8B C01A C2B N1B -6.9(3) . . . . ?
N2B N1B C2B C7B -87.7(2) . . . . ?
P1B N1B C2B C7B 79.5(2) . . . . ?
N2B N1B C2B C01A 91.7(2) . . . . ?
P1B N1B C2B C01A -101.0(2) . . . . ?
C2B C01A C4B C5B 0.2(3) . . . . ?
C8B C01A C4B C5B -174.4(2) . . . . ?
C01A C4B C5B C6B 1.5(3) . . . . ?
C4B C5B C6B C7B -1.5(4) . . . . ?
C5B C6B C7B C2B -0.3(3) . . . . ?
C5B C6B C7B C11B 176.0(2) . . . . ?
C01A C2B C7B C6B 2.0(3) . . . . ?
N1B C2B C7B C6B -178.49(19) . . . . ?
C01A C2B C7B C11B -174.1(2) . . . . ?
N1B C2B C7B C11B 5.4(3) . . . . ?
C4B C01A C8B C10B -36.5(3) . . . . ?
C2B C01A C8B C10B 149.1(2) . . . . ?
C4B C01A C8B C9B 86.5(2) . . . . ?
C2B C01A C8B C9B -87.8(2) . . . . ?
C6B C7B C11B C13B -73.8(3) . . . . ?
C2B C7B C11B C13B 102.2(3) . . . . ?
C6B C7B C11B C12B 51.0(3) . . . . ?
C2B C7B C11B C12B -133.0(2) . . . . ?
N3B C1B C14B C15B 142.7(2) . . . . ?
P1B C1B C14B C15B -36.1(3) . . . . ?
N3B C1B C14B C17B -97.3(2) . . . . ?
P1B C1B C14B C17B 83.9(2) . . . . ?
N3B C1B C14B C16B 23.4(3) . . . . ?
P1B C1B C14B C16B -155.40(18) . . . . ?
