#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:14:28 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272590 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/52/1565229.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_1565229
loop_
_publ_author_name
'Li, Peng-Fei'
'Ai, Yong'
'Zeng, Yu-Ling'
'Liu, Jun-Chao'
'Xu, Zhe-Kun'
'Wang, Zhong-Xia'
_publ_section_title
;
 Highest-Tc single-component homochiral organic ferroelectrics
;
_journal_issue                   3
_journal_name_full               'Chemical Science'
_journal_page_first              657
_journal_page_last               664
_journal_paper_doi               10.1039/D1SC04322F
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C10 H15 N O2 S'
_chemical_formula_sum            'C10 H15 N O2 S'
_chemical_formula_weight         213.29
_chemical_name_systematic        Rac-CSAI
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-06-02 deposited with the CCDC.	2021-11-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.8730(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.69900(10)
_cell_length_b                   7.61190(10)
_cell_length_c                   8.95990(10)
_cell_measurement_reflns_used    2745
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.3550
_cell_measurement_theta_min      5.7610
_cell_volume                     523.188(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0117
_diffrn_reflns_av_unetI/netI     0.0094
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2983
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.517
_diffrn_reflns_theta_min         5.767
_exptl_absorpt_coefficient_mu    2.546
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.037(7)
_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   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         1099
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.215
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0352P)²+0.3974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1093
_reflns_number_total             1099
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04322f2.cif
_cod_data_source_block           P21
_cod_depositor_comments
'Adding full bibliography for 1565226--1565230.cif.'
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               1565229
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
S1 S 0.28906(6) 0.2500 0.39729(5) 0.0191(2) Uani 1 2 d S T P . .
O1 O 0.31162(15) 0.41110(15) 0.31794(12) 0.0277(3) Uani 1 1 d . . . . .
C1 C 0.4156(3) 0.2500 0.5765(2) 0.0196(5) Uani 1 2 d S T P . .
H1A H 0.5082 0.3347 0.5788 0.023 Uiso 0.5 1 d R U P . .
H1B H 0.4640 0.1360 0.5998 0.023 Uiso 0.5 1 d R U P . .
N1 N 0.0890(2) 0.2500 0.4591(2) 0.0260(5) Uani 1 2 d S T P . .
C2 C 0.1045(3) 0.2500 0.6004(3) 0.0232(5) Uani 1 2 d S T P . .
C4 C -0.0287(3) 0.2500 0.7133(3) 0.0269(5) Uani 1 2 d S T P . .
H4A H -0.1009 0.1471 0.7044 0.032 Uiso 0.5 1 d R U P . .
H4B H -0.1009 0.3529 0.7044 0.032 Uiso 0.5 1 d R U P . .
C5 C 0.0893(4) 0.2500 0.8600(3) 0.0663(13) Uani 1 2 d DS T P . .
H5A H 0.0422 0.2026 0.9473 0.080 Uiso 0.5 1 d R U P . .
C9 C 0.4137(3) 0.2500 0.9495(3) 0.0438(8) Uani 1 2 d DS T P . .
H9A H 0.4043 0.1852 1.0403 0.066 Uiso 0.5 1 d R U P . .
H9B H 0.5242 0.2256 0.9116 0.066 Uiso 0.5 1 d R U P . .
H9C H 0.4050 0.3735 0.9694 0.066 Uiso 0.5 1 d R U P . .
C10 C 0.2413(5) -0.0036(5) 0.8045(5) 0.0259(9) Uani 0.5 1 d D . P . .
H10A H 0.1461 -0.0237 0.7302 0.039 Uiso 0.5 1 d R U P . .
H10B H 0.3467 -0.0496 0.7697 0.039 Uiso 0.5 1 d R U P . .
H10C H 0.2182 -0.0614 0.8960 0.039 Uiso 0.5 1 d R U P . .
C3 C 0.2800(3) 0.3001(4) 0.6841(3) 0.0194(7) Uani 0.5 1 d D . P . .
C6 C 0.1394(5) 0.4829(5) 0.8606(4) 0.0270(7) Uani 0.5 1 d D . P . .
H6A H 0.1948 0.5195 0.9555 0.032 Uiso 0.5 1 d R U P . .
H6B H 0.0363 0.5519 0.8375 0.032 Uiso 0.5 1 d R U P . .
C7 C 0.2666(5) 0.4944(5) 0.7355(5) 0.0223(8) Uani 0.5 1 d D . P . .
H7A H 0.2193 0.5677 0.6547 0.027 Uiso 0.5 1 d R U P . .
H7B H 0.3782 0.5394 0.7734 0.027 Uiso 0.5 1 d R U P . .
C8 C 0.2623(4) 0.1941(4) 0.8300(3) 0.0226(7) Uani 0.5 1 d D . P . .
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O1 S1 O1 117.37(10) 4_565 . ?
O1 S1 N1 108.43(6) 4_565 . ?
O1 S1 N1 108.43(6) . . ?
O1 S1 C1 111.19(5) 4_565 . ?
O1 S1 C1 111.19(6) . . ?
N1 S1 C1 98.47(9) . . ?
C3 C1 C3 28.9(2) . 4_565 ?
C3 C1 S1 102.41(15) . . ?
C3 C1 S1 102.41(15) 4_565 . ?
C3 C1 H1A 111.4 . . ?
C3 C1 H1A 134.4 4_565 . ?
S1 C1 H1A 111.3 . . ?
C3 C1 H1B 111.2 . . ?
C3 C1 H1B 84.9 4_565 . ?
S1 C1 H1B 111.3 . . ?
H1A C1 H1B 109.2 . . ?
C2 N1 S1 108.63(15) . . ?
N1 C2 C4 131.7(2) . . ?
N1 C2 C3 119.6(2) . 4_565 ?
C4 C2 C3 107.10(19) . 4_565 ?
N1 C2 C3 119.6(2) . . ?
C4 C2 C3 107.10(19) . . ?
C3 C2 C3 28.8(2) 4_565 . ?
C2 C4 C5 100.89(19) . . ?
C2 C4 H4A 111.6 . . ?
C5 C4 H4A 111.6 . . ?
C2 C4 H4B 111.6 . . ?
C5 C4 H4B 111.6 . . ?
H4A C4 H4B 109.4 . . ?
C8 C5 C8 34.3(3) . 4_565 ?
C8 C5 C4 109.2(2) . . ?
C8 C5 C4 109.2(2) 4_565 . ?
C8 C5 C6 60.89(17) . 4_565 ?
C8 C5 C6 95.1(2) 4_565 4_565 ?
C4 C5 C6 96.48(15) . 4_565 ?
C8 C5 C6 95.1(2) . . ?
C8 C5 C6 60.89(17) 4_565 . ?
C4 C5 C6 96.48(15) . . ?
C6 C5 C6 155.5(3) 4_565 . ?
C8 C5 H5A 117.3 . . ?
C8 C5 H5A 132.9 4_565 . ?
C4 C5 H5A 117.5 . . ?
C6 C5 H5A 74.1 4_565 . ?
C6 C5 H5A 117.4 . . ?
C8 C9 C8 31.4(2) 4_565 . ?
C8 C9 H9A 127.7 4_565 . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 116.1 4_565 . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 78.6 4_565 . ?
C8 C9 H9C 109.4 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 C6 140.1(8) 4_565 4_565 ?
C7 C10 C8 90.0(6) 4_565 . ?
C6 C10 C8 81.0(3) 4_565 . ?
C7 C10 C3 47.6(5) 4_565 4_565 ?
C6 C10 C3 109.1(4) 4_565 4_565 ?
C8 C10 C3 43.32(18) . 4_565 ?
C7 C10 H10A 68.9 4_565 . ?
C6 C10 H10A 77.5 4_565 . ?
C8 C10 H10A 109.0 . . ?
C3 C10 H10A 83.4 4_565 . ?
C7 C10 H10B 54.3 4_565 . ?
C6 C10 H10B 164.0 4_565 . ?
C8 C10 H10B 109.1 . . ?
C3 C10 H10B 86.3 4_565 . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 158.2 4_565 . ?
C6 C10 H10C 54.6 4_565 . ?
C8 C10 H10C 110.4 . . ?
C3 C10 H10C 153.6 4_565 . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C3 C8 91.90(18) 4_565 4_565 ?
C3 C3 C1 75.54(11) 4_565 . ?
C8 C3 C1 139.7(3) 4_565 . ?
C3 C3 C2 75.62(11) 4_565 . ?
C8 C3 C2 109.2(2) 4_565 . ?
C1 C3 C2 104.47(19) . . ?
C3 C3 C8 58.68(15) 4_565 . ?
C8 C3 C8 33.2(2) 4_565 . ?
C1 C3 C8 121.0(2) . . ?
C2 C3 C8 98.3(2) . . ?
C3 C3 C7 161.99(18) 4_565 . ?
C8 C3 C7 70.2(2) 4_565 . ?
C1 C3 C7 119.4(2) . . ?
C2 C3 C7 107.6(2) . . ?
C8 C3 C7 103.4(2) . . ?
C3 C3 C10 143.55(16) 4_565 4_565 ?
C8 C3 C10 52.2(2) 4_565 4_565 ?
C1 C3 C10 134.5(2) . 4_565 ?
C2 C3 C10 107.5(2) . 4_565 ?
C8 C3 C10 85.2(2) . 4_565 ?
C7 C3 C10 18.48(16) . 4_565 ?
C10 C6 C7 16.0(3) 4_565 . ?
C10 C6 C8 63.9(3) 4_565 4_565 ?
C7 C6 C8 62.0(2) . 4_565 ?
C10 C6 C5 109.6(3) 4_565 . ?
C7 C6 C5 101.6(3) . . ?
C8 C6 C5 48.64(16) 4_565 . ?
C10 C6 H6A 95.3 4_565 . ?
C7 C6 H6A 111.3 . . ?
C8 C6 H6A 99.4 4_565 . ?
C5 C6 H6A 111.4 . . ?
C10 C6 H6B 119.0 4_565 . ?
C7 C6 H6B 111.9 . . ?
C8 C6 H6B 150.4 4_565 . ?
C5 C6 H6B 111.3 . . ?
H6A C6 H6B 109.2 . . ?
C10 C7 C6 23.9(5) 4_565 . ?
C10 C7 C3 113.9(6) 4_565 . ?
C6 C7 C3 102.8(3) . . ?
C10 C7 C8 66.4(5) 4_565 4_565 ?
C6 C7 C8 62.8(2) . 4_565 ?
C3 C7 C8 48.47(18) . 4_565 ?
C10 C7 H7A 121.1 4_565 . ?
C6 C7 H7A 110.8 . . ?
C3 C7 H7A 111.1 . . ?
C8 C7 H7A 149.3 4_565 . ?
C10 C7 H7B 87.6 4_565 . ?
C6 C7 H7B 111.4 . . ?
C3 C7 H7B 111.3 . . ?
C8 C7 H7B 100.5 4_565 . ?
H7A C7 H7B 109.3 . . ?
C8 C8 C3 88.10(18) 4_565 4_565 ?
C8 C8 C5 72.87(13) 4_565 . ?
C3 C8 C5 110.3(3) 4_565 . ?
C8 C8 C10 169.9(2) 4_565 . ?
C3 C8 C10 84.5(3) 4_565 . ?
C5 C8 C10 103.3(3) . . ?
C8 C8 C3 58.68(15) 4_565 . ?
C3 C8 C3 29.4(2) 4_565 . ?
C5 C8 C3 98.8(2) . . ?
C10 C8 C3 113.7(3) . . ?
C8 C8 C9 74.30(11) 4_565 . ?
C3 C8 C9 121.9(3) 4_565 . ?
C5 C8 C9 115.8(2) . . ?
C10 C8 C9 115.5(2) . . ?
C3 C8 C9 108.6(2) . . ?
C8 C8 C7 149.35(17) 4_565 4_565 ?
C3 C8 C7 61.3(2) 4_565 4_565 ?
C5 C8 C7 114.0(2) . 4_565 ?
C10 C8 C7 23.59(16) . 4_565 ?
C3 C8 C7 90.7(2) . 4_565 ?
C9 C8 C7 122.2(2) . 4_565 ?
C8 C8 C6 143.23(17) 4_565 4_565 ?
C3 C8 C6 107.1(3) 4_565 4_565 ?
C5 C8 C6 70.47(19) . 4_565 ?
C10 C8 C6 35.1(2) . 4_565 ?
C3 C8 C6 130.1(2) . 4_565 ?
C9 C8 C6 120.0(2) . 4_565 ?
C7 C8 C6 55.20(19) 4_565 4_565 ?
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 O1 1.4354(11) 4_565 ?
S1 O1 1.4354(11) . ?
S1 N1 1.6807(19) . ?
S1 C1 1.806(2) . ?
C1 C3 1.528(3) . ?
C1 C3 1.528(3) 4_565 ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
N1 C2 1.261(3) . ?
C2 C4 1.501(3) . ?
C2 C3 1.537(3) 4_565 ?
C2 C3 1.537(3) . ?
C4 C5 1.533(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C5 C8 1.445(4) . ?
C5 C8 1.445(4) 4_565 ?
C5 C6 1.814(4) 4_565 ?
C5 C6 1.814(4) . ?
C5 H5A 0.9600 . ?
C9 C8 1.573(4) 4_565 ?
C9 C8 1.573(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C7 0.668(4) 4_565 ?
C10 C6 0.979(5) 4_565 ?
C10 C8 1.529(5) . ?
C10 C3 1.925(5) 4_565 ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9601 . ?
C3 C3 0.763(6) 4_565 ?
C3 C8 1.327(4) 4_565 ?
C3 C8 1.553(4) . ?
C3 C7 1.555(5) . ?
C3 C10 1.925(5) 4_565 ?
C6 C10 0.979(5) 4_565 ?
C6 C7 1.552(5) . ?
C6 C8 1.681(4) 4_565 ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C7 C10 0.668(4) 4_565 ?
C7 C8 1.668(5) 4_565 ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C8 C8 0.851(6) 4_565 ?
C8 C3 1.327(4) 4_565 ?
C8 C7 1.668(5) 4_565 ?
C8 C6 1.681(4) 4_565 ?
