#------------------------------------------------------------------------------
#$Date: 2022-10-07 00:58:33 +0300 (Fri, 07 Oct 2022) $
#$Revision: 278385 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/08/7130824.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_7130824
loop_
_publ_author_name
'Bawari, Deependra'
'Volodarsky , Solomon'
'Ginzburg, Yael'
'Jaiswal, Kuldeep'
'Joshi, Pooja'
'Dobrovetsky, Roman'
_publ_section_title
;
 Intramolecular C−N Bond Activation by Geometrically Constrained
 PIII-Centre
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04359A
_journal_year                    2022
_chemical_formula_moiety         'C33 H47 Cl N3 O2 P'
_chemical_formula_sum            'C33 H47 Cl N3 O2 P'
_chemical_formula_weight         584.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-02-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-07-19 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.4690(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.5759(5)
_cell_length_b                   11.0110(4)
_cell_length_c                   36.5877(12)
_cell_measurement_reflns_used    55159
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.505
_cell_measurement_theta_min      2.183
_cell_volume                     7080.5(4)
_computing_cell_refinement       'Saint, Bruker-AXS'
_computing_data_collection       'Apex2, Bruker-AXS'
_computing_data_reduction        'Saint, Bruker-AXS'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 1.75
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'ApexDuo, Bruker-AXS'
_diffrn_measurement_method       '1 deg. φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            55159
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.183
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, Bruker-AXS'
_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    1.096
_exptl_crystal_description       plate
_exptl_crystal_F_000             2512
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.156
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         8144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0470P)²+8.9314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1264
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6217
_reflns_number_total             8144
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc04359a2.cif
_cod_data_source_block           rom148
_cod_database_code               7130824
_shelx_shelxl_version_number     2017/1
_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   0.972
_shelx_estimated_absorpt_t_min   0.952
_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(C32A) = Uanis(C32B)
Uanis(C33A) = Uanis(C33B) = Uanis(C32A) = Uanis(C32B)
Uanis(Cl1B) = Uanis(Cl1A)
Uanis(C34B) = Uanis(C34A)
Uanis(N3A) = Uanis(N3B)
Uanis(C32B) = Uanis(C32A) = Uanis(C33A) = Uanis(C33B) = Uanis(C34A) =
Uanis(C34B)
Uanis(Cl1A) = Uanis(Cl1B)
3. Others
 Sof(Cl1B)=Sof(C32B)=Sof(H32B)=Sof(C33A)=Sof(H33c)=Sof(H33d)=Sof(C34B)=
 Sof(N3B)=1-FVAR(1)
 Sof(C32A)=Sof(H32A)=Sof(N3A)=Sof(C34A)=Sof(Cl1A)=Sof(C33B)=Sof(H33a)=
 Sof(H33b)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C32A(H32A), C32B(H32B)
4.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C16(H16a,H16b), C33B(H33a,H33b), C33A(H33c,H33d)
4.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C7(H7), C19(H19), C13(H13)
4.d Idealised Me refined as rotating group:
 C24(H24a,H24b,H24c), C30(H30a,H30b,H30c), C29(H29a,H29b,H29c), C23(H23a,H23b,
 H23c), C5(H5a,H5b,H5c), C28(H28a,H28b,H28c), C11(H11a,H11b,H11c), C4(H4a,H4b,
 H4c), C12(H12a,H12b,H12c), C10(H10a,H10b,H10c), C22(H22a,H22b,H22c), C6(H6a,
 H6b,H6c)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.30697(3) 0.30804(5) 0.59861(2) 0.01872(12) Uani 1 1 d . . . . .
C32A C 0.2366(2) 0.2374(4) 0.56586(11) 0.0281(5) Uani 0.643(4) 1 d . . P A 1
H32A H 0.277790 0.222522 0.547711 0.034 Uiso 0.643(4) 1 calc R U P A 1
O2 O 0.27640(7) 0.24964(12) 0.63857(3) 0.0189(3) Uani 1 1 d . . . . .
O1 O 0.26939(7) 0.43749(12) 0.61325(4) 0.0208(3) Uani 1 1 d . . . . .
N2 N 0.37557(9) 0.19744(14) 0.59758(4) 0.0202(3) Uani 1 1 d . . . . .
N1 N 0.36295(9) 0.38867(15) 0.56988(4) 0.0232(4) Uani 1 1 d . . . . .
C25 C 0.34881(10) -0.01663(17) 0.68850(5) 0.0184(4) Uani 1 1 d . . . . .
H25 H 0.339841 -0.064974 0.709536 0.022 Uiso 1 1 calc R U . . .
C20 C 0.41019(10) -0.04726(17) 0.66637(5) 0.0184(4) Uani 1 1 d . . . . .
C26 C 0.29939(10) 0.08144(17) 0.68160(5) 0.0170(4) Uani 1 1 d . . . . .
C27 C 0.23409(11) 0.11494(17) 0.70720(5) 0.0191(4) Uani 1 1 d . . . . .
C31 C 0.31469(10) 0.14635(16) 0.65015(5) 0.0163(4) Uani 1 1 d . . . . .
C18 C 0.37417(10) 0.11671(17) 0.62691(5) 0.0178(4) Uani 1 1 d . . . . .
C15 C 0.29263(10) 0.54017(17) 0.59417(5) 0.0194(4) Uani 1 1 d . . . . .
C2 C 0.26576(10) 0.65681(17) 0.59953(5) 0.0188(4) Uani 1 1 d . . . . .
C7 C 0.29894(10) 0.74541(17) 0.57709(5) 0.0194(4) Uani 1 1 d . . . . .
H7 H 0.282224 0.826993 0.579652 0.023 Uiso 1 1 calc R U . . .
C19 C 0.42269(11) 0.02143(17) 0.63477(5) 0.0206(4) Uani 1 1 d . . . . .
H19 H 0.463804 0.002823 0.619034 0.025 Uiso 1 1 calc R U . . .
C21 C 0.46603(11) -0.14890(18) 0.67683(5) 0.0216(4) Uani 1 1 d . . . . .
C8 C 0.35483(10) 0.72106(17) 0.55132(5) 0.0190(4) Uani 1 1 d . . . . .
N3A N 0.0912(12) 0.0403(19) 0.5362(2) 0.0317(16) Uani 0.643(4) 1 d . . P A 1
C3 C 0.20238(11) 0.68495(18) 0.62657(5) 0.0215(4) Uani 1 1 d . . . . .
C13 C 0.37991(11) 0.60160(18) 0.54702(5) 0.0209(4) Uani 1 1 d . . . . .
H13 H 0.417969 0.582164 0.529682 0.025 Uiso 1 1 calc R U . . .
C9 C 0.38850(11) 0.82080(18) 0.52697(5) 0.0226(4) Uani 1 1 d . . . . .
C24 C 0.43547(11) -0.23260(19) 0.70658(6) 0.0264(4) Uani 1 1 d . . . . .
H24A H 0.427478 -0.185826 0.729007 0.040 Uiso 1 1 calc R U . . .
H24B H 0.472252 -0.297679 0.711366 0.040 Uiso 1 1 calc R U . . .
H24C H 0.387053 -0.268003 0.698443 0.040 Uiso 1 1 calc R U . . .
C30 C 0.15834(11) 0.1145(2) 0.68598(6) 0.0264(5) Uani 1 1 d . . . . .
H30A H 0.159998 0.175682 0.666562 0.040 Uiso 1 1 calc R U . . .
H30B H 0.116665 0.133271 0.702681 0.040 Uiso 1 1 calc R U . . .
H30C H 0.150032 0.034088 0.675149 0.040 Uiso 1 1 calc R U . . .
C14 C 0.34816(11) 0.51273(18) 0.56849(5) 0.0202(4) Uani 1 1 d . . . . .
C17 C 0.44466(11) 0.22073(18) 0.57686(5) 0.0245(4) Uani 1 1 d . . . . .
H17A H 0.459423 0.148171 0.562601 0.029 Uiso 1 1 calc R U . . .
H17B H 0.487265 0.243135 0.593400 0.029 Uiso 1 1 calc R U . . .
C16 C 0.42418(12) 0.32636(19) 0.55147(6) 0.0270(5) Uani 1 1 d . . . . .
H16A H 0.468324 0.380969 0.548124 0.032 Uiso 1 1 calc R U . . .
H16B H 0.407208 0.296178 0.527252 0.032 Uiso 1 1 calc R U . . .
C29 C 0.24872(13) 0.24217(19) 0.72288(6) 0.0289(5) Uani 1 1 d . . . . .
H29A H 0.296646 0.242083 0.736758 0.043 Uiso 1 1 calc R U . . .
H29B H 0.206876 0.264753 0.739069 0.043 Uiso 1 1 calc R U . . .
H29C H 0.251959 0.300928 0.702837 0.043 Uiso 1 1 calc R U . . .
C23 C 0.53919(11) -0.0891(2) 0.69131(6) 0.0291(5) Uani 1 1 d . . . . .
H23A H 0.560540 -0.036600 0.672355 0.044 Uiso 1 1 calc R U . . .
H23B H 0.576230 -0.152164 0.697849 0.044 Uiso 1 1 calc R U . . .
H23C H 0.527514 -0.040414 0.712970 0.044 Uiso 1 1 calc R U . . .
C5 C 0.13156(11) 0.6110(2) 0.61646(5) 0.0258(4) Uani 1 1 d . . . . .
H5A H 0.115150 0.631773 0.591575 0.039 Uiso 1 1 calc R U . . .
H5B H 0.090637 0.629762 0.633599 0.039 Uiso 1 1 calc R U . . .
H5C H 0.143546 0.524201 0.617745 0.039 Uiso 1 1 calc R U . . .
C28 C 0.22665(13) 0.0258(2) 0.73889(6) 0.0297(5) Uani 1 1 d . . . . .
H28A H 0.216706 -0.055766 0.729286 0.044 Uiso 1 1 calc R U . . .
H28B H 0.184445 0.050834 0.754533 0.044 Uiso 1 1 calc R U . . .
H28C H 0.274006 0.025199 0.753215 0.044 Uiso 1 1 calc R U . . .
C11 C 0.35253(13) 0.94451(19) 0.53368(6) 0.0312(5) Uani 1 1 d . . . . .
H11A H 0.297988 0.940583 0.528018 0.047 Uiso 1 1 calc R U . . .
H11B H 0.376651 1.005188 0.517969 0.047 Uiso 1 1 calc R U . . .
H11C H 0.359794 0.967381 0.559353 0.047 Uiso 1 1 calc R U . . .
C4 C 0.22770(12) 0.6525(2) 0.66558(6) 0.0336(5) Uani 1 1 d . . . . .
H4A H 0.243493 0.567174 0.666448 0.050 Uiso 1 1 calc R U . . .
H4B H 0.185260 0.665183 0.682365 0.050 Uiso 1 1 calc R U . . .
H4C H 0.270518 0.704373 0.672862 0.050 Uiso 1 1 calc R U . . .
C12 C 0.47467(11) 0.8309(2) 0.53432(6) 0.0298(5) Uani 1 1 d . . . . .
H12A H 0.483502 0.854117 0.559868 0.045 Uiso 1 1 calc R U . . .
H12B H 0.496425 0.892732 0.518210 0.045 Uiso 1 1 calc R U . . .
H12C H 0.498904 0.752424 0.529567 0.045 Uiso 1 1 calc R U . . .
C10 C 0.37564(14) 0.7879(2) 0.48649(5) 0.0344(5) Uani 1 1 d . . . . .
H10A H 0.399601 0.709440 0.481320 0.052 Uiso 1 1 calc R U . . .
H10B H 0.398220 0.850663 0.471001 0.052 Uiso 1 1 calc R U . . .
H10C H 0.320917 0.782575 0.481393 0.052 Uiso 1 1 calc R U . . .
C22 C 0.48418(15) -0.2270(2) 0.64327(6) 0.0392(6) Uani 1 1 d . . . . .
H22A H 0.436754 -0.258506 0.632665 0.059 Uiso 1 1 calc R U . . .
H22B H 0.516873 -0.294984 0.650629 0.059 Uiso 1 1 calc R U . . .
H22C H 0.510510 -0.177391 0.625081 0.059 Uiso 1 1 calc R U . . .
C34A C 0.1393(4) 0.0854(6) 0.55312(13) 0.0281(5) Uani 0.643(4) 1 d . . P A 1
C6 C 0.18027(14) 0.8192(2) 0.62587(7) 0.0407(6) Uani 1 1 d . . . . .
H6A H 0.224856 0.868922 0.631986 0.061 Uiso 1 1 calc R U . . .
H6B H 0.140151 0.833999 0.643781 0.061 Uiso 1 1 calc R U . . .
H6C H 0.161635 0.840879 0.601411 0.061 Uiso 1 1 calc R U . . .
Cl1A Cl 0.1939(3) 0.3513(5) 0.53627(9) 0.0405(6) Uani 0.643(4) 1 d . . P A 1
C33B C 0.1839(2) 0.1475(3) 0.58367(9) 0.0281(5) Uani 0.643(4) 1 d . . P A 2
H33A H 0.226034 0.090938 0.589572 0.034 Uiso 0.643(4) 1 calc R U P A 2
H33B H 0.156329 0.161132 0.606797 0.034 Uiso 0.643(4) 1 calc R U P A 2
Cl1B Cl 0.1843(6) 0.3488(10) 0.54456(18) 0.0405(6) Uani 0.357(4) 1 d . . P A 2
C32B C 0.2195(4) 0.2620(7) 0.5749(2) 0.0281(5) Uani 0.357(4) 1 d . . P A 2
H32B H 0.188442 0.303340 0.594015 0.034 Uiso 0.357(4) 1 calc R U P A 2
C33A C 0.2190(4) 0.1283(5) 0.56546(17) 0.0281(5) Uani 0.357(4) 1 d . . P A 1
H33C H 0.227305 0.097078 0.590553 0.034 Uiso 0.357(4) 1 calc R U P A 1
H33D H 0.256306 0.086575 0.549666 0.034 Uiso 0.357(4) 1 calc R U P A 1
C34B C 0.1331(7) 0.0818(11) 0.5606(2) 0.0281(5) Uani 0.357(4) 1 d . . P A 2
N3B N 0.089(2) 0.041(4) 0.5444(6) 0.0317(16) Uani 0.357(4) 1 d . . 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
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
O2 P1 C32A 100.46(14) . . ?
O2 P1 N2 88.70(7) . . ?
O2 P1 N1 157.79(8) . . ?
O2 P1 C32B 91.9(2) . . ?
O1 P1 C32A 107.38(14) . . ?
O1 P1 O2 85.27(6) . . ?
O1 P1 N2 153.90(8) . . ?
O1 P1 N1 89.13(7) . . ?
O1 P1 C32B 93.2(2) . . ?
N2 P1 C32A 98.68(14) . . ?
N2 P1 C32B 112.4(2) . . ?
N1 P1 C32A 101.72(14) . . ?
N1 P1 N2 86.93(8) . . ?
N1 P1 C32B 109.9(2) . . ?
P1 C32A H32A 90.8 . . ?
Cl1A C32A P1 111.1(3) . . ?
Cl1A C32A H32A 90.8 . . ?
C33A C32A P1 124.7(4) . . ?
C33A C32A H32A 90.8 . . ?
C33A C32A Cl1A 124.1(4) . . ?
C31 O2 P1 114.83(11) . . ?
C15 O1 P1 114.59(11) . . ?
C18 N2 P1 114.79(12) . . ?
C18 N2 C17 122.14(15) . . ?
C17 N2 P1 118.36(13) . . ?
C14 N1 P1 115.31(13) . . ?
C14 N1 C16 125.99(16) . . ?
C16 N1 P1 118.53(13) . . ?
C20 C25 H25 118.0 . . ?
C20 C25 C26 124.07(17) . . ?
C26 C25 H25 118.0 . . ?
C25 C20 C19 118.42(17) . . ?
C25 C20 C21 121.81(16) . . ?
C19 C20 C21 119.69(16) . . ?
C25 C26 C27 122.63(16) . . ?
C31 C26 C25 114.95(16) . . ?
C31 C26 C27 122.41(16) . . ?
C26 C27 C30 109.91(15) . . ?
C26 C27 C29 108.93(16) . . ?
C29 C27 C30 109.52(16) . . ?
C28 C27 C26 112.28(15) . . ?
C28 C27 C30 107.61(17) . . ?
C28 C27 C29 108.55(16) . . ?
O2 C31 C18 111.77(15) . . ?
C26 C31 O2 125.53(16) . . ?
C26 C31 C18 122.64(17) . . ?
C31 C18 N2 109.81(16) . . ?
C19 C18 N2 129.06(17) . . ?
C19 C18 C31 121.11(17) . . ?
O1 C15 C14 111.85(16) . . ?
C2 C15 O1 125.53(16) . . ?
C2 C15 C14 122.62(17) . . ?
C15 C2 C7 114.71(17) . . ?
C15 C2 C3 122.14(16) . . ?
C7 C2 C3 123.09(17) . . ?
C2 C7 H7 118.0 . . ?
C8 C7 C2 124.07(18) . . ?
C8 C7 H7 118.0 . . ?
C20 C19 H19 120.6 . . ?
C18 C19 C20 118.78(17) . . ?
C18 C19 H19 120.6 . . ?
C20 C21 C23 107.79(16) . . ?
C24 C21 C20 112.95(16) . . ?
C24 C21 C23 108.15(16) . . ?
C24 C21 C22 107.98(18) . . ?
C22 C21 C20 110.22(16) . . ?
C22 C21 C23 109.72(18) . . ?
C7 C8 C13 118.85(17) . . ?
C7 C8 C9 122.15(17) . . ?
C13 C8 C9 118.99(17) . . ?
C2 C3 C5 109.37(16) . . ?
C2 C3 C4 110.36(16) . . ?
C2 C3 C6 111.83(16) . . ?
C5 C3 C4 109.28(16) . . ?
C6 C3 C5 107.71(18) . . ?
C6 C3 C4 108.22(19) . . ?
C8 C13 H13 120.8 . . ?
C14 C13 C8 118.40(17) . . ?
C14 C13 H13 120.8 . . ?
C8 C9 C12 109.49(15) . . ?
C8 C9 C10 109.60(16) . . ?
C11 C9 C8 112.57(16) . . ?
C11 C9 C12 108.43(17) . . ?
C11 C9 C10 107.92(17) . . ?
C10 C9 C12 108.75(17) . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N1 C14 C15 108.65(16) . . ?
C13 C14 N1 130.00(18) . . ?
C13 C14 C15 121.35(18) . . ?
N2 C17 H17A 110.8 . . ?
N2 C17 H17B 110.8 . . ?
N2 C17 C16 104.85(15) . . ?
H17A C17 H17B 108.9 . . ?
C16 C17 H17A 110.8 . . ?
C16 C17 H17B 110.8 . . ?
N1 C16 C17 104.47(15) . . ?
N1 C16 H16A 110.9 . . ?
N1 C16 H16B 110.9 . . ?
C17 C16 H16A 110.9 . . ?
C17 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 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 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3A C34A C33A 161.2(10) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
H33A C33B H33B 106.2 . . ?
C32B C33B H33A 105.9 . . ?
C32B C33B H33B 105.9 . . ?
C34B C33B H33A 105.9 . . ?
C34B C33B H33B 105.9 . . ?
C34B C33B C32B 125.7(5) . . ?
P1 C32B H32B 90.2 . . ?
C33B C32B P1 120.0(5) . . ?
C33B C32B Cl1B 121.0(6) . . ?
C33B C32B H32B 90.2 . . ?
Cl1B C32B P1 119.0(6) . . ?
Cl1B C32B H32B 90.2 . . ?
C32A C33A C34A 121.7(5) . . ?
C32A C33A H33C 106.9 . . ?
C32A C33A H33D 106.9 . . ?
C34A C33A H33C 106.9 . . ?
C34A C33A H33D 106.9 . . ?
H33C C33A H33D 106.7 . . ?
N3B C34B C33B 172(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
P1 C32A 1.883(4) . ?
P1 O2 1.6889(13) . ?
P1 O1 1.6614(14) . ?
P1 N2 1.7144(16) . ?
P1 N1 1.6965(16) . ?
P1 C32B 1.831(8) . ?
C32A H32A 1.0000 . ?
C32A Cl1A 1.815(6) . ?
C32A C33A 1.240(7) . ?
O2 C31 1.386(2) . ?
O1 C15 1.392(2) . ?
N2 C18 1.394(2) . ?
N2 C17 1.459(2) . ?
N1 C14 1.391(3) . ?
N1 C16 1.447(2) . ?
C25 H25 0.9500 . ?
C25 C20 1.396(3) . ?
C25 C26 1.407(2) . ?
C20 C19 1.400(3) . ?
C20 C21 1.535(3) . ?
C26 C27 1.532(2) . ?
C26 C31 1.383(2) . ?
C27 C30 1.536(3) . ?
C27 C29 1.535(3) . ?
C27 C28 1.525(3) . ?
C31 C18 1.392(2) . ?
C18 C19 1.381(3) . ?
C15 C2 1.383(3) . ?
C15 C14 1.394(3) . ?
C2 C7 1.405(3) . ?
C2 C3 1.528(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.393(3) . ?
C19 H19 0.9500 . ?
C21 C24 1.527(3) . ?
C21 C23 1.535(3) . ?
C21 C22 1.535(3) . ?
C8 C13 1.397(3) . ?
C8 C9 1.536(3) . ?
N3A C34A 1.16(2) . ?
C3 C5 1.530(3) . ?
C3 C4 1.534(3) . ?
C3 C6 1.529(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.376(3) . ?
C9 C11 1.522(3) . ?
C9 C12 1.540(3) . ?
C9 C10 1.540(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C16 1.530(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C34A C33A 1.543(9) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C33B H33A 0.9900 . ?
C33B H33B 0.9900 . ?
C33B C32B 1.443(8) . ?
C33B C34B 1.421(12) . ?
Cl1B C32B 1.587(11) . ?
C32B H32B 1.0000 . ?
C33A H33C 0.9900 . ?
C33A H33D 0.9900 . ?
C34B N3B 1.07(4) . ?
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 C32A C33A C34A 149.7(4) . . . . ?
P1 O2 C31 C26 -179.07(15) . . . . ?
P1 O2 C31 C18 3.6(2) . . . . ?
P1 O1 C15 C2 175.54(15) . . . . ?
P1 O1 C15 C14 -5.1(2) . . . . ?
P1 N2 C18 C31 0.8(2) . . . . ?
P1 N2 C18 C19 -177.45(17) . . . . ?
P1 N2 C17 C16 -17.7(2) . . . . ?
P1 N1 C14 C15 4.5(2) . . . . ?
P1 N1 C14 C13 -176.31(17) . . . . ?
P1 N1 C16 C17 -26.9(2) . . . . ?
C32A P1 O2 C31 96.05(17) . . . . ?
C32A P1 O1 C15 -95.69(18) . . . . ?
C32A P1 N2 C18 -99.46(18) . . . . ?
C32A P1 N2 C17 104.33(19) . . . . ?
C32A P1 N1 C14 101.32(19) . . . . ?
C32A P1 N1 C16 -83.2(2) . . . . ?
O2 P1 C32A Cl1A 129.3(2) . . . . ?
O2 P1 C32A C33A -47.8(6) . . . . ?
O2 P1 O1 C15 164.81(13) . . . . ?
O2 P1 N2 C18 0.93(14) . . . . ?
O2 P1 N2 C17 -155.28(15) . . . . ?
O2 P1 N1 C14 -81.5(2) . . . . ?
O2 P1 N1 C16 94.0(2) . . . . ?
O2 P1 C32B C33B -38.0(6) . . . . ?
O2 P1 C32B Cl1B 142.6(6) . . . . ?
O2 C31 C18 N2 -2.7(2) . . . . ?
O2 C31 C18 C19 175.76(17) . . . . ?
O1 P1 C32A Cl1A 41.1(3) . . . . ?
O1 P1 C32A C33A -136.1(6) . . . . ?
O1 P1 O2 C31 -157.12(13) . . . . ?
O1 P1 N2 C18 77.4(2) . . . . ?
O1 P1 N2 C17 -78.8(2) . . . . ?
O1 P1 N1 C14 -6.26(15) . . . . ?
O1 P1 N1 C16 169.24(16) . . . . ?
O1 P1 C32B C33B -123.3(5) . . . . ?
O1 P1 C32B Cl1B 57.2(6) . . . . ?
O1 C15 C2 C7 179.24(17) . . . . ?
O1 C15 C2 C3 -3.4(3) . . . . ?
O1 C15 C14 N1 0.3(2) . . . . ?
O1 C15 C14 C13 -178.98(17) . . . . ?
N2 P1 C32A Cl1A -140.4(2) . . . . ?
N2 P1 C32A C33A 42.5(6) . . . . ?
N2 P1 O2 C31 -2.54(13) . . . . ?
N2 P1 O1 C15 87.6(2) . . . . ?
N2 P1 N1 C14 -160.44(15) . . . . ?
N2 P1 N1 C16 15.06(16) . . . . ?
N2 P1 C32B C33B 51.4(6) . . . . ?
N2 P1 C32B Cl1B -128.0(5) . . . . ?
N2 C18 C19 C20 179.45(19) . . . . ?
N2 C17 C16 N1 25.1(2) . . . . ?
N1 P1 C32A Cl1A -51.7(2) . . . . ?
N1 P1 C32A C33A 131.1(6) . . . . ?
N1 P1 O2 C31 -81.2(2) . . . . ?
N1 P1 O1 C15 6.33(13) . . . . ?
N1 P1 N2 C18 159.14(15) . . . . ?
N1 P1 N2 C17 2.93(15) . . . . ?
N1 P1 C32B C33B 146.4(5) . . . . ?
N1 P1 C32B Cl1B -33.0(6) . . . . ?
C25 C20 C19 C18 0.3(3) . . . . ?
C25 C20 C21 C24 16.2(3) . . . . ?
C25 C20 C21 C23 -103.2(2) . . . . ?
C25 C20 C21 C22 137.1(2) . . . . ?
C25 C26 C27 C30 -123.38(19) . . . . ?
C25 C26 C27 C29 116.6(2) . . . . ?
C25 C26 C27 C28 -3.6(3) . . . . ?
C25 C26 C31 O2 -176.74(17) . . . . ?
C25 C26 C31 C18 0.4(3) . . . . ?
C20 C25 C26 C27 -177.95(18) . . . . ?
C20 C25 C26 C31 1.3(3) . . . . ?
C26 C25 C20 C19 -1.7(3) . . . . ?
C26 C25 C20 C21 175.04(18) . . . . ?
C26 C31 C18 N2 179.85(17) . . . . ?
C26 C31 C18 C19 -1.7(3) . . . . ?
C27 C26 C31 O2 2.5(3) . . . . ?
C27 C26 C31 C18 179.65(17) . . . . ?
C31 C26 C27 C30 57.4(2) . . . . ?
C31 C26 C27 C29 -62.6(2) . . . . ?
C31 C26 C27 C28 177.15(18) . . . . ?
C31 C18 C19 C20 1.3(3) . . . . ?
C18 N2 C17 C16 -172.03(17) . . . . ?
C15 C2 C7 C8 -0.3(3) . . . . ?
C15 C2 C3 C5 -57.7(2) . . . . ?
C15 C2 C3 C4 62.5(2) . . . . ?
C15 C2 C3 C6 -176.9(2) . . . . ?
C2 C15 C14 N1 179.72(18) . . . . ?
C2 C15 C14 C13 0.4(3) . . . . ?
C2 C7 C8 C13 0.3(3) . . . . ?
C2 C7 C8 C9 179.01(17) . . . . ?
C7 C2 C3 C5 119.4(2) . . . . ?
C7 C2 C3 C4 -120.4(2) . . . . ?
C7 C2 C3 C6 0.2(3) . . . . ?
C7 C8 C13 C14 0.0(3) . . . . ?
C7 C8 C9 C11 -1.6(3) . . . . ?
C7 C8 C9 C12 119.1(2) . . . . ?
C7 C8 C9 C10 -121.7(2) . . . . ?
C19 C20 C21 C24 -167.08(18) . . . . ?
C19 C20 C21 C23 73.5(2) . . . . ?
C19 C20 C21 C22 -46.2(3) . . . . ?
C21 C20 C19 C18 -176.50(17) . . . . ?
C8 C13 C14 N1 -179.51(19) . . . . ?
C8 C13 C14 C15 -0.4(3) . . . . ?
N3A C34A C33A C32A 113(3) . . . . ?
C3 C2 C7 C8 -177.58(17) . . . . ?
C13 C8 C9 C11 177.11(17) . . . . ?
C13 C8 C9 C12 -62.2(2) . . . . ?
C13 C8 C9 C10 57.0(2) . . . . ?
C9 C8 C13 C14 -178.70(17) . . . . ?
C14 N1 C16 C17 148.07(19) . . . . ?
C14 C15 C2 C7 -0.1(3) . . . . ?
C14 C15 C2 C3 177.23(18) . . . . ?
C17 N2 C18 C31 156.07(17) . . . . ?
C17 N2 C18 C19 -22.2(3) . . . . ?
C16 N1 C14 C15 -170.61(18) . . . . ?
C16 N1 C14 C13 8.6(3) . . . . ?
Cl1A C32A C33A C34A -27.1(9) . . . . ?
C32B P1 O2 C31 109.8(3) . . . . ?
C32B P1 O1 C15 -103.6(3) . . . . ?
C32B P1 N2 C18 -90.6(3) . . . . ?
C32B P1 N2 C17 113.2(3) . . . . ?
C32B P1 N1 C14 86.8(3) . . . . ?
C32B P1 N1 C16 -97.7(3) . . . . ?
C34B C33B C32B P1 -157.9(6) . . . . ?
C34B C33B C32B Cl1B 21.5(11) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.130 0.250 292.7 64.9 ?
2 0.000 -0.130 0.750 292.7 64.9 ?
3 0.500 0.370 0.750 292.7 64.9 ?
4 0.500 0.630 0.250 292.7 64.9 ?
