#------------------------------------------------------------------------------
#$Date: 2022-09-24 01:58:21 +0300 (Sat, 24 Sep 2022) $
#$Revision: 278140 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/13/7711333.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_7711333
loop_
_publ_author_name
'Sanjay Kumar, Siddharth'
'Rangarajan, Shalini'
'Kunchur, Harish S.'
'Balakrishna, Maravanji Shivaramaiah'
_publ_section_title
;
 A greener approach towards the synthesis of N-heterocyclic thiones and
 selones using mechanochemical technique
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT02322A
_journal_year                    2022
_chemical_formula_moiety         'C20 H23 N2 O P S'
_chemical_formula_sum            'C20 H23 N2 O P S'
_chemical_formula_weight         370.43
_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             2022-07-05
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-12 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.860(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6482(15)
_cell_length_b                   21.1068(17)
_cell_length_c                   9.3551(10)
_cell_measurement_reflns_used    2713
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.9340
_cell_measurement_theta_min      2.2720
_cell_volume                     1937.4(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  70.00   1.00    8.00    --  -20.00  72.00 -36.00  129
  2  ω    -59.00  44.00   1.00    8.00    --  -20.00  72.00-108.00  103
  3  ω    -69.00 -21.00   1.00    8.00    --  -20.00 -72.00  36.00   48
  4  ω   -110.00 -45.00   1.00    8.00    --  -20.00 -72.00-108.00   65
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0536122000
_diffrn_orient_matrix_UB_12      -0.0005067000
_diffrn_orient_matrix_UB_13      0.0745991000
_diffrn_orient_matrix_UB_21      0.0055308000
_diffrn_orient_matrix_UB_22      0.0334498000
_diffrn_orient_matrix_UB_23      -0.0022546000
_diffrn_orient_matrix_UB_31      -0.0481381000
_diffrn_orient_matrix_UB_32      0.0032383000
_diffrn_orient_matrix_UB_33      0.0347369000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1067
_diffrn_reflns_av_unetI/netI     0.1188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12285
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.076
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3409
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1453
_refine_ls_R_factor_gt           0.0752
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0521P)²+1.1930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1921
_reflns_number_total             3409
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt02322a2.cif
_cod_data_source_block           comp_5
_cod_database_code               7711333
_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.
;
_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. Restrained distances
 N1-C17A \\sim N1-C17B
 with sigma of 0.02
 C17A-C18A \\sim C17B-C18B
 with sigma of 0.02
 C18A-C19A \\sim C18B-C19B
 with sigma of 0.02
 C20A-C19A \\sim C20B-C19B
 with sigma of 0.02
 C18A-C20A \\sim C18B-C20B
 with sigma of 0.04
 N1-C18A \\sim N1-C18B
 with sigma of 0.04
 C17A-C19A \\sim C17B-C19B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C18B) \\sim Ueq, Uanis(C19B) \\sim Ueq, Uanis(C20B) \\sim Ueq: with sigma
of 0.02 and sigma for terminal atoms of 0.04
4. Rigid body (RIGU) restrains
 C17A, C18A, C20A, C19A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C17B, C18B, C20B, C19B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C17A(0.575) H17A(0.575) H17B(0.575) C18A(0.575) H18A(0.575)
 H18B(0.575) C20A(0.575) H20A(0.575) H20B(0.575) H20C(0.575) C19A(0.575)
 H19A(0.575) H19B(0.575) C17B(0.425) H17C(0.425) H17D(0.425) C18B(0.425)
 H18C(0.425) H18D(0.425) C19B(0.425) H19C(0.425) H19D(0.425) C20B(0.425)
 H20D(0.425) H20E(0.425) H20F(0.425)
6.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C17A(H17A,H17B), C18A(H18A,H18B), C19A(H19A,H19B), C17B(H17C,
 H17D), C18B(H18C,H18D), C19B(H19C,H19D)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C14(H14), C16(H16), C7(H7), C3(H3), C2(H2), C12(H12),
 C8(H8), C15(H15), C13(H13), C9(H9)
6.c Idealised Me refined as rotating group:
 C20A(H20A,H20B,H20C), C20B(H20D,H20E,H20F)
;
_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 2.420
_oxdiff_exptl_absorpt_empirical_full_min 0.685
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 0.08631(15) 0.40347(6) 0.64101(14) 0.0417(4) Uani 1 1 d . . . . .
S1 S 0.46304(15) 0.37701(6) 0.52312(15) 0.0544(4) Uani 1 1 d . . . . .
O1 O 0.0159(4) 0.45645(14) 0.6838(4) 0.0500(10) Uani 1 1 d . . . . .
N2 N 0.3076(4) 0.45890(17) 0.6101(4) 0.0409(10) Uani 1 1 d . . . . .
N1 N 0.5229(5) 0.48211(18) 0.7091(5) 0.0459(11) Uani 1 1 d D . . . .
C5 C -0.0304(5) 0.3448(2) 0.5244(5) 0.0356(11) Uani 1 1 d . . . . .
C11 C 0.2085(5) 0.3642(2) 0.8092(5) 0.0396(12) Uani 1 1 d . . . . .
C6 C 0.0090(5) 0.2931(2) 0.4569(5) 0.0437(12) Uani 1 1 d . . . . .
H6 H 0.100549 0.287187 0.475507 0.052 Uiso 1 1 calc R U . . .
C1 C 0.4313(6) 0.4401(2) 0.6148(5) 0.0440(13) Uani 1 1 d . . . . .
C10 C -0.1674(6) 0.3508(2) 0.4982(5) 0.0494(14) Uani 1 1 d . . . . .
H10 H -0.195449 0.384069 0.543877 0.059 Uiso 1 1 calc R U . . .
C14 C 0.3844(6) 0.3021(3) 1.0727(6) 0.0591(16) Uani 1 1 d . . . . .
H14 H 0.442606 0.280836 1.160459 0.071 Uiso 1 1 calc R U . . .
C16 C 0.1921(5) 0.3698(2) 0.9476(5) 0.0452(13) Uani 1 1 d . . . . .
H16 H 0.121948 0.394742 0.952622 0.054 Uiso 1 1 calc R U . . .
C4 C 0.1789(5) 0.4278(2) 0.5215(5) 0.0446(13) Uani 1 1 d . . . . .
H4A H 0.196390 0.390698 0.470781 0.054 Uiso 1 1 calc R U . . .
H4B H 0.122064 0.456403 0.441387 0.054 Uiso 1 1 calc R U . . .
C7 C -0.0865(5) 0.2511(2) 0.3634(6) 0.0514(14) Uani 1 1 d . . . . .
H7 H -0.059533 0.217685 0.317005 0.062 Uiso 1 1 calc R U . . .
C3 C 0.3231(6) 0.5119(2) 0.7034(6) 0.0524(15) Uani 1 1 d . . . . .
H3 H 0.254162 0.533296 0.721007 0.063 Uiso 1 1 calc R U . . .
C2 C 0.4545(7) 0.5262(2) 0.7626(6) 0.0557(15) Uani 1 1 d . . . . .
H2 H 0.494185 0.559889 0.828685 0.067 Uiso 1 1 calc R U . . .
C12 C 0.3153(6) 0.3275(2) 0.8055(6) 0.0585(16) Uani 1 1 d . . . . .
H12 H 0.327901 0.323415 0.712970 0.070 Uiso 1 1 calc R U . . .
C8 C -0.2228(6) 0.2585(3) 0.3382(6) 0.0571(15) Uani 1 1 d . . . . .
H8 H -0.287181 0.229825 0.275872 0.068 Uiso 1 1 calc R U . . .
C15 C 0.2797(6) 0.3386(3) 1.0804(6) 0.0605(17) Uani 1 1 d . . . . .
H15 H 0.267604 0.342277 1.173269 0.073 Uiso 1 1 calc R U . . .
C13 C 0.4029(6) 0.2971(2) 0.9366(6) 0.0597(16) Uani 1 1 d . . . . .
H13 H 0.474678 0.273128 0.932430 0.072 Uiso 1 1 calc R U . . .
C9 C -0.2626(6) 0.3083(3) 0.4059(6) 0.0578(15) Uani 1 1 d . . . . .
H9 H -0.353982 0.313338 0.389254 0.069 Uiso 1 1 calc R U . . .
C17A C 0.6696(11) 0.4784(11) 0.7607(19) 0.050(5) Uani 0.575 1 d D . P A 1
H17A H 0.709207 0.520485 0.777464 0.059 Uiso 0.575 1 calc R U P A 1
H17B H 0.694557 0.456966 0.683785 0.059 Uiso 0.575 1 calc R U P A 1
C18A C 0.7210(10) 0.4401(6) 0.9158(13) 0.057(3) Uani 0.575 1 d D . P A 1
H18A H 0.702265 0.463319 0.994804 0.069 Uiso 0.575 1 calc R U P A 1
H18B H 0.675038 0.399497 0.900494 0.069 Uiso 0.575 1 calc R U P A 1
C20A C 0.9330(11) 0.3948(7) 1.1161(13) 0.056(4) Uani 0.575 1 d D . P A 1
H20A H 0.894858 0.352996 1.105093 0.084 Uiso 0.575 1 calc R U P A 1
H20B H 0.916948 0.416887 1.197113 0.084 Uiso 0.575 1 calc R U P A 1
H20C H 1.029312 0.391845 1.141917 0.084 Uiso 0.575 1 calc R U P A 1
C19A C 0.8658(10) 0.4310(5) 0.9633(12) 0.063(3) Uani 0.575 1 d D . P A 1
H19A H 0.909119 0.472092 0.973711 0.075 Uiso 0.575 1 calc R U P A 1
H19B H 0.882110 0.408042 0.882232 0.075 Uiso 0.575 1 calc R U P A 1
C17B C 0.6661(14) 0.4836(19) 0.732(3) 0.066(9) Uani 0.425 1 d D . P A 2
H17C H 0.686671 0.525952 0.707726 0.079 Uiso 0.425 1 calc R U P A 2
H17D H 0.678158 0.455077 0.657345 0.079 Uiso 0.425 1 calc R U P A 2
C18B C 0.7735(18) 0.4660(8) 0.894(2) 0.099(7) Uani 0.425 1 d D U P A 2
H18C H 0.863637 0.472196 0.893690 0.118 Uiso 0.425 1 calc R U P A 2
H18D H 0.764106 0.494719 0.970276 0.118 Uiso 0.425 1 calc R U P A 2
C19B C 0.763(2) 0.4039(8) 0.939(2) 0.106(7) Uani 0.425 1 d D U P A 2
H19C H 0.771746 0.375944 0.861170 0.127 Uiso 0.425 1 calc R U P A 2
H19D H 0.671922 0.398324 0.936648 0.127 Uiso 0.425 1 calc R U P A 2
C20B C 0.8647(17) 0.3813(11) 1.099(2) 0.075(7) Uani 0.425 1 d D U P A 2
H20D H 0.947120 0.367223 1.089975 0.113 Uiso 0.425 1 calc R U P A 2
H20E H 0.825240 0.346899 1.134254 0.113 Uiso 0.425 1 calc R U P A 2
H20F H 0.884953 0.415619 1.171605 0.113 Uiso 0.425 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
S S 0.1246 0.1234 '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
O1 P1 C5 112.4(2) . . ?
O1 P1 C11 112.3(2) . . ?
O1 P1 C4 113.7(2) . . ?
C5 P1 C11 107.9(2) . . ?
C5 P1 C4 103.4(2) . . ?
C11 P1 C4 106.5(2) . . ?
C1 N2 C4 125.0(4) . . ?
C1 N2 C3 109.7(4) . . ?
C3 N2 C4 125.3(4) . . ?
C1 N1 C2 109.0(5) . . ?
C1 N1 C17A 126.2(10) . . ?
C1 N1 C17B 123.9(18) . . ?
C2 N1 C17A 124.4(11) . . ?
C2 N1 C17B 126.7(18) . . ?
C6 C5 P1 123.6(4) . . ?
C10 C5 P1 118.5(3) . . ?
C10 C5 C6 117.9(5) . . ?
C16 C11 P1 117.9(4) . . ?
C16 C11 C12 118.5(4) . . ?
C12 C11 P1 123.6(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.7(5) . . ?
C7 C6 H6 119.6 . . ?
N2 C1 S1 126.6(4) . . ?
N1 C1 S1 127.6(4) . . ?
N1 C1 N2 105.8(4) . . ?
C5 C10 H10 119.4 . . ?
C9 C10 C5 121.3(5) . . ?
C9 C10 H10 119.4 . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.3(5) . . ?
C11 C16 H16 119.6 . . ?
C11 C16 C15 120.7(5) . . ?
C15 C16 H16 119.6 . . ?
P1 C4 H4A 109.0 . . ?
P1 C4 H4B 109.0 . . ?
N2 C4 P1 113.0(3) . . ?
N2 C4 H4A 109.0 . . ?
N2 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.1(5) . . ?
C8 C7 H7 119.9 . . ?
N2 C3 H3 126.4 . . ?
C2 C3 N2 107.2(5) . . ?
C2 C3 H3 126.4 . . ?
N1 C2 H2 125.9 . . ?
C3 C2 N1 108.3(5) . . ?
C3 C2 H2 125.9 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(5) . . ?
C13 C12 H12 119.5 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.8(5) . . ?
C9 C8 H8 120.1 . . ?
C14 C15 C16 119.4(5) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C14 C13 C12 120.0(6) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C10 C9 C8 120.2(5) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
N1 C17A H17A 110.5 . . ?
N1 C17A H17B 110.5 . . ?
N1 C17A C18A 106.3(9) . . ?
H17A C17A H17B 108.7 . . ?
C18A C17A H17A 110.5 . . ?
C18A C17A H17B 110.5 . . ?
C17A C18A H18A 110.2 . . ?
C17A C18A H18B 110.2 . . ?
H18A C18A H18B 108.5 . . ?
C19A C18A C17A 107.6(9) . . ?
C19A C18A H18A 110.2 . . ?
C19A C18A H18B 110.2 . . ?
H20A C20A H20B 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
C18A C19A C20A 114.2(9) . . ?
C18A C19A H19A 108.7 . . ?
C18A C19A H19B 108.7 . . ?
C20A C19A H19A 108.7 . . ?
C20A C19A H19B 108.7 . . ?
H19A C19A H19B 107.6 . . ?
N1 C17B H17C 107.7 . . ?
N1 C17B H17D 107.7 . . ?
N1 C17B C18B 118.4(16) . . ?
H17C C17B H17D 107.1 . . ?
C18B C17B H17C 107.7 . . ?
C18B C17B H17D 107.7 . . ?
C17B C18B H18C 108.8 . . ?
C17B C18B H18D 108.8 . . ?
H18C C18B H18D 107.7 . . ?
C19B C18B C17B 113.9(19) . . ?
C19B C18B H18C 108.8 . . ?
C19B C18B H18D 108.8 . . ?
C18B C19B H19C 107.7 . . ?
C18B C19B H19D 107.7 . . ?
C18B C19B C20B 118.5(16) . . ?
H19C C19B H19D 107.1 . . ?
C20B C19B H19C 107.7 . . ?
C20B C19B H19D 107.7 . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20E 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.485(3) . ?
P1 C5 1.793(5) . ?
P1 C11 1.807(5) . ?
P1 C4 1.827(5) . ?
S1 C1 1.688(5) . ?
N2 C1 1.360(6) . ?
N2 C4 1.454(6) . ?
N2 C3 1.388(6) . ?
N1 C1 1.359(6) . ?
N1 C2 1.389(6) . ?
N1 C17A 1.447(11) . ?
N1 C17B 1.454(14) . ?
C5 C6 1.404(6) . ?
C5 C10 1.388(7) . ?
C11 C16 1.377(6) . ?
C11 C12 1.387(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(6) . ?
C10 H10 0.9300 . ?
C10 C9 1.377(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(7) . ?
C14 C13 1.366(7) . ?
C16 H16 0.9300 . ?
C16 C15 1.396(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C7 H7 0.9300 . ?
C7 C8 1.386(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.324(7) . ?
C2 H2 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.378(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(7) . ?
C15 H15 0.9300 . ?
C13 H13 0.9300 . ?
C9 H9 0.9300 . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C17A C18A 1.562(13) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C18A C19A 1.442(11) . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
C20A C19A 1.531(12) . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?
C17B C18B 1.545(15) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C18B C19B 1.394(15) . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C19B C20B 1.541(15) . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?
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 C5 C6 C7 -177.4(4) . . . . ?
P1 C5 C10 C9 178.0(4) . . . . ?
P1 C11 C16 C15 177.4(4) . . . . ?
P1 C11 C12 C13 -178.0(4) . . . . ?
O1 P1 C5 C6 173.9(3) . . . . ?
O1 P1 C5 C10 -5.7(4) . . . . ?
O1 P1 C11 C16 22.2(4) . . . . ?
O1 P1 C11 C12 -159.5(4) . . . . ?
O1 P1 C4 N2 77.1(4) . . . . ?
N2 C3 C2 N1 -0.7(6) . . . . ?
N1 C17A C18A C19A 175.2(12) . . . . ?
N1 C17B C18B C19B 63(4) . . . . ?
C5 P1 C11 C16 -102.2(4) . . . . ?
C5 P1 C11 C12 76.1(5) . . . . ?
C5 P1 C4 N2 -160.7(3) . . . . ?
C5 C6 C7 C8 -1.8(7) . . . . ?
C5 C10 C9 C8 0.5(8) . . . . ?
C11 P1 C5 C6 -61.8(4) . . . . ?
C11 P1 C5 C10 118.6(4) . . . . ?
C11 P1 C4 N2 -47.1(4) . . . . ?
C11 C16 C15 C14 0.6(8) . . . . ?
C11 C12 C13 C14 0.8(9) . . . . ?
C6 C5 C10 C9 -1.5(7) . . . . ?
C6 C7 C8 C9 0.6(8) . . . . ?
C1 N2 C4 P1 123.8(4) . . . . ?
C1 N2 C3 C2 1.1(5) . . . . ?
C1 N1 C2 C3 0.2(6) . . . . ?
C1 N1 C17A C18A -90.3(14) . . . . ?
C1 N1 C17B C18B -113(3) . . . . ?
C10 C5 C6 C7 2.2(7) . . . . ?
C16 C11 C12 C13 0.3(8) . . . . ?
C4 P1 C5 C6 50.8(4) . . . . ?
C4 P1 C5 C10 -128.8(4) . . . . ?
C4 P1 C11 C16 147.3(4) . . . . ?
C4 P1 C11 C12 -34.4(5) . . . . ?
C4 N2 C1 S1 -1.0(6) . . . . ?
C4 N2 C1 N1 179.5(4) . . . . ?
C4 N2 C3 C2 -179.4(4) . . . . ?
C7 C8 C9 C10 0.0(8) . . . . ?
C3 N2 C1 S1 178.5(4) . . . . ?
C3 N2 C1 N1 -1.0(5) . . . . ?
C3 N2 C4 P1 -55.6(5) . . . . ?
C2 N1 C1 S1 -179.0(4) . . . . ?
C2 N1 C1 N2 0.5(5) . . . . ?
C2 N1 C17A C18A 82.4(15) . . . . ?
C2 N1 C17B C18B 75(3) . . . . ?
C12 C11 C16 C15 -1.0(7) . . . . ?
C15 C14 C13 C12 -1.3(8) . . . . ?
C13 C14 C15 C16 0.6(8) . . . . ?
C17A N1 C1 S1 -5.3(9) . . . . ?
C17A N1 C1 N2 174.1(8) . . . . ?
C17A N1 C2 C3 -173.6(8) . . . . ?
C17A C18A C19A C20A 179.1(13) . . . . ?
C17B N1 C1 S1 7.7(11) . . . . ?
C17B N1 C1 N2 -172.9(10) . . . . ?
C17B N1 C2 C3 173.3(10) . . . . ?
C17B C18B C19B C20B -179.7(19) . . . . ?
