#------------------------------------------------------------------------------
#$Date: 2021-11-17 04:54:45 +0200 (Wed, 17 Nov 2021) $
#$Revision: 270712 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/52/1565272.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_1565272
loop_
_publ_author_name
'Tian, Yu'
'Yang, Jie'
'Gao, Mingxue'
'Liu, Zhenjiang'
'Zhao, M.'
'Fang, Manman'
'Li, Zhen'
_publ_section_title
;
 Organic Microporous Crystals Driven by Pure C-H‧‧‧π
 Interactions with Vapors-Induced Crystal-to-Crystal Transformations
;
_journal_name_full               'Materials Horizons'
_journal_paper_doi               10.1039/D1MH01360B
_journal_year                    2021
_chemical_formula_moiety         'C36 H22 N2 S3, C Cl2'
_chemical_formula_sum            'C37 H24 Cl2 N2 S3'
_chemical_formula_weight         663.66
_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
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc261rst
_audit_creation_date             2020-05-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-05 deposited with the CCDC.	2021-11-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 126.4255(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.9381(4)
_cell_length_b                   7.91274(10)
_cell_length_c                   18.0152(2)
_cell_measurement_reflns_used    4421
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.816
_cell_measurement_theta_min      4.9140
_cell_volume                     3089.79(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5642
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         4.079
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.00171(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2768
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0488
_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)+(0.0784P)²+3.3316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2572
_reflns_number_total             2768
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1mh01360b2.cif
_cod_data_source_block           a
_cod_database_code               1565272
_shelx_shelxl_version_number     2014/7
_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   0.689
_shelx_estimated_absorpt_t_min   0.584
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 Cl1-C19
 1.76 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq, Uanis(Cl1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(Cl1) = Uanis(Cl1A)
4. Others
 Sof(Cl1A)=1-FVAR(1)
 Sof(Cl1)=FVAR(1)
 Fixed Sof: C19(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16),
 C17(H17), C18(H18)
;
_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
S1 S 0.5000 0.52107(10) 0.2500 0.0483(3) Uani 1 2 d S T P . .
S2 S 0.27343(3) -0.33873(8) 0.23070(5) 0.0556(2) Uani 1 1 d . . . . .
N1 N 0.35314(7) -0.0459(2) 0.24292(12) 0.0388(4) Uani 1 1 d . . . . .
C1 C 0.47317(8) 0.2025(3) 0.25022(12) 0.0333(4) Uani 1 1 d . . . . .
C2 C 0.45410(9) 0.3669(3) 0.25092(14) 0.0376(5) Uani 1 1 d . . . . .
C3 C 0.40313(10) 0.3968(3) 0.25119(16) 0.0430(5) Uani 1 1 d . . . . .
H3 H 0.3911 0.5064 0.2523 0.052 Uiso 1 1 calc R . . . .
C4 C 0.37113(9) 0.2603(3) 0.24986(15) 0.0428(5) Uani 1 1 d . . . . .
H4 H 0.3372 0.2777 0.2504 0.051 Uiso 1 1 calc R . . . .
C5 C 0.38899(9) 0.0953(3) 0.24776(14) 0.0376(5) Uani 1 1 d . . . . .
C6 C 0.43959(8) 0.0650(3) 0.24844(13) 0.0351(4) Uani 1 1 d . . . . .
H6 H 0.4513 -0.0452 0.2477 0.042 Uiso 1 1 calc R . . . .
C7 C 0.28052(11) 0.0192(3) 0.07812(15) 0.0462(5) Uani 1 1 d . . . . .
H7 H 0.3079 0.0999 0.0844 0.055 Uiso 1 1 calc R . . . .
C8 C 0.22528(12) -0.0077(4) -0.00779(17) 0.0554(6) Uani 1 1 d . . . . .
H8 H 0.2165 0.0525 -0.0587 0.067 Uiso 1 1 calc R . . . .
C9 C 0.18346(12) -0.1228(4) -0.01808(18) 0.0610(7) Uani 1 1 d . . . . .
H9 H 0.1457 -0.1379 -0.0752 0.073 Uiso 1 1 calc R . . . .
C10 C 0.19788(11) -0.2157(3) 0.05698(19) 0.0563(7) Uani 1 1 d . . . . .
H10 H 0.1696 -0.2934 0.0502 0.068 Uiso 1 1 calc R . . . .
C11 C 0.25404(10) -0.1948(3) 0.14247(16) 0.0426(5) Uani 1 1 d . . . . .
C12 C 0.29591(9) -0.0723(3) 0.15536(14) 0.0372(5) Uani 1 1 d . . . . .
C13 C 0.36184(9) -0.0896(3) 0.32612(14) 0.0371(5) Uani 1 1 d . . . . .
C14 C 0.32678(10) -0.2171(3) 0.32856(16) 0.0435(5) Uani 1 1 d . . . . .
C15 C 0.33553(12) -0.2569(4) 0.41050(19) 0.0592(7) Uani 1 1 d . . . . .
H15 H 0.3107 -0.3385 0.4105 0.071 Uiso 1 1 calc R . . . .
C16 C 0.38026(14) -0.1782(4) 0.49172(19) 0.0644(7) Uani 1 1 d . . . . .
H16 H 0.3861 -0.2069 0.5465 0.077 Uiso 1 1 calc R . . . .
C17 C 0.41645(12) -0.0558(4) 0.49090(17) 0.0574(7) Uani 1 1 d . . . . .
H17 H 0.4473 -0.0030 0.5456 0.069 Uiso 1 1 calc R . . . .
C18 C 0.40704(10) -0.0112(3) 0.40889(15) 0.0479(5) Uani 1 1 d . . . . .
H18 H 0.4314 0.0727 0.4093 0.057 Uiso 1 1 calc R . . . .
C19 C 0.4808(5) 0.5575(13) 0.4968(8) 0.131(4) Uani 0.5 1 d D U . . .
Cl1 Cl 0.4953(2) 0.3515(5) 0.5480(3) 0.1403(10) Uani 0.560(4) 1 d D U . A 1
Cl1A Cl 0.4591(3) 0.4103(6) 0.5123(4) 0.1403(10) Uani 0.440(4) 1 d . . . 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C2 S1 C2 91.24(14) . 2_655 ?
C14 S2 C11 100.29(11) . . ?
C12 N1 C5 115.22(17) . . ?
C13 N1 C5 116.15(17) . . ?
C13 N1 C12 121.84(16) . . ?
C2 C1 C1 111.84(11) . 2_655 ?
C2 C1 C6 119.03(17) . . ?
C6 C1 C1 129.12(11) . 2_655 ?
C1 C2 S1 112.54(14) . . ?
C3 C2 S1 125.87(17) . . ?
C3 C2 C1 121.58(19) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.4(2) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.78(18) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 N1 119.64(17) . . ?
C6 C5 N1 119.22(19) . . ?
C6 C5 C4 121.13(19) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 119.08(19) . . ?
C5 C6 H6 120.5 . . ?
C8 C7 H7 119.3 . . ?
C8 C7 C12 121.4(2) . . ?
C12 C7 H7 119.3 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.4(2) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 S2 117.93(19) . . ?
C10 C11 C12 120.5(2) . . ?
C12 C11 S2 121.34(17) . . ?
C7 C12 N1 120.98(19) . . ?
C7 C12 C11 117.5(2) . . ?
C11 C12 N1 121.5(2) . . ?
C14 C13 N1 121.26(19) . . ?
C18 C13 N1 120.99(19) . . ?
C18 C13 C14 117.7(2) . . ?
C13 C14 S2 121.87(17) . . ?
C15 C14 S2 117.66(19) . . ?
C15 C14 C13 120.4(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.2(2) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 119.0(2) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.2(2) . . ?
C17 C18 H18 119.4 . . ?
C19 C19 Cl1 54.2(9) 5_666 . ?
C19 C19 Cl1 79.2(12) 5_666 5_666 ?
C19 C19 Cl1A 79.0(11) 5_666 . ?
C19 C19 Cl1A 52.4(10) 5_666 5_666 ?
Cl1 C19 Cl1 133.4(6) 5_666 . ?
Cl1A C19 Cl1A 131.4(6) . 5_666 ?
C19 Cl1 C19 46.6(6) 5_666 . ?
C19 Cl1A C19 48.6(6) . 5_666 ?
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
S1 C2 1.744(2) . ?
S1 C2 1.744(2) 2_655 ?
S2 C11 1.764(2) . ?
S2 C14 1.758(2) . ?
N1 C5 1.445(3) . ?
N1 C12 1.421(3) . ?
N1 C13 1.416(3) . ?
C1 C1 1.450(4) 2_655 ?
C1 C2 1.401(3) . ?
C1 C6 1.403(3) . ?
C2 C3 1.396(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.400(3) . ?
C5 C6 1.377(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.386(3) . ?
C7 C12 1.395(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.373(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(3) . ?
C11 C12 1.398(3) . ?
C13 C14 1.400(3) . ?
C13 C18 1.391(3) . ?
C14 C15 1.386(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.374(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(3) . ?
C18 H18 0.9300 . ?
C19 C19 1.331(18) 5_666 ?
C19 Cl1 1.798(12) . ?
C19 Cl1 1.485(14) 5_666 ?
C19 Cl1A 1.740(14) 5_666 ?
C19 Cl1A 1.404(14) . ?
Cl1 C19 1.485(14) 5_666 ?
Cl1A C19 1.740(14) 5_666 ?
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
S1 C2 C3 C4 178.57(16) . . . . ?
S2 C11 C12 N1 -7.0(3) . . . . ?
S2 C11 C12 C7 170.53(16) . . . . ?
S2 C14 C15 C16 174.1(2) . . . . ?
N1 C5 C6 C1 178.01(17) . . . . ?
N1 C13 C14 S2 3.9(3) . . . . ?
N1 C13 C14 C15 -179.3(2) . . . . ?
N1 C13 C18 C17 -178.9(2) . . . . ?
C1 C1 C2 S1 0.5(3) 2_655 . . . ?
C1 C1 C2 C3 179.8(2) 2_655 . . . ?
C1 C1 C6 C5 -178.9(2) 2_655 . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 S1 C2 C1 -0.20(10) 2_655 . . . ?
C2 S1 C2 C3 -179.5(2) 2_655 . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 N1 -177.7(2) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C5 N1 C12 C7 8.1(3) . . . . ?
C5 N1 C12 C11 -174.45(18) . . . . ?
C5 N1 C13 C14 175.87(18) . . . . ?
C5 N1 C13 C18 -6.3(3) . . . . ?
C6 C1 C2 S1 -178.38(14) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C7 C8 C9 C10 -2.4(4) . . . . ?
C8 C7 C12 N1 178.9(2) . . . . ?
C8 C7 C12 C11 1.4(3) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 S2 -171.2(2) . . . . ?
C9 C10 C11 C12 3.5(4) . . . . ?
C10 C11 C12 N1 178.5(2) . . . . ?
C10 C11 C12 C7 -3.9(3) . . . . ?
C11 S2 C14 C13 -27.2(2) . . . . ?
C11 S2 C14 C15 155.99(19) . . . . ?
C12 N1 C5 C4 74.7(2) . . . . ?
C12 N1 C5 C6 -104.1(2) . . . . ?
C12 N1 C13 C14 26.1(3) . . . . ?
C12 N1 C13 C18 -156.1(2) . . . . ?
C12 C7 C8 C9 1.8(4) . . . . ?
C13 N1 C5 C4 -77.1(2) . . . . ?
C13 N1 C5 C6 104.2(2) . . . . ?
C13 N1 C12 C7 158.1(2) . . . . ?
C13 N1 C12 C11 -24.4(3) . . . . ?
C13 C14 C15 C16 -2.8(4) . . . . ?
C14 S2 C11 C10 -156.76(18) . . . . ?
C14 S2 C11 C12 28.6(2) . . . . ?
C14 C13 C18 C17 -1.0(3) . . . . ?
C14 C15 C16 C17 0.8(4) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C16 C17 C18 C13 -0.9(4) . . . . ?
C18 C13 C14 S2 -173.95(17) . . . . ?
C18 C13 C14 C15 2.8(3) . . . . ?
Cl1 C19 Cl1 C19 -0.002(3) 5_666 . . 5_666 ?
Cl1A C19 Cl1A C19 0.003(2) 5_666 . . 5_666 ?
