Chemical Design Homochiral Heterocyclic Organic Ferroelectric Crystals
Song, Xian-Jiang; Tang, Shu-Yu; Chen, Xiao-Gang; Ai, Yong; Chemical Communications  (2022) –; doi:10.1039/D2CC03881A

data_7130549
_publ_section_title
;
 Chemical Design Homochiral Heterocyclic Organic Ferroelectric Crystals
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03881A
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C13 H19 N O4 S'
_chemical_formula_sum            'C13 H19 N O4 S'
_chemical_formula_weight         285.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-06
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2022-08-09 deposited with the CCDC.	2022-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.214(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7428(3)
_cell_length_b                   7.0274(2)
_cell_length_c                   12.3154(4)
_cell_measurement_reflns_used    5770
_cell_measurement_temperature    292.6(2)
_cell_measurement_theta_max      30.7480
_cell_measurement_theta_min      1.8080
_cell_volume                     663.23(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.6(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.813
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     10.00  51.00   0.50    1.20    --    5.05  37.00-120.00   82
  2  \w    -38.00  20.00   0.50    1.20    --    5.05 -57.00  29.00  116
  3  \w     -7.00  26.00   0.50    1.20    --    5.05  57.00 171.00   66
  4  \w     32.00  78.00   0.50    1.20    --    5.05  57.00 171.00   92
  5  \w    -18.00   7.00   0.50    1.20    --   -5.21 -99.00   0.00   50
  6  \w    -17.00  16.00   0.50    1.20    --   -5.21 -99.00  30.00   66
  7  \w    -18.00  28.00   0.50    1.20    --   -5.21 -99.00-150.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0088947000
_diffrn_orient_matrix_UB_12      -0.0130809000
_diffrn_orient_matrix_UB_13      0.0576528000
_diffrn_orient_matrix_UB_21      -0.0672057000
_diffrn_orient_matrix_UB_22      0.0674686000
_diffrn_orient_matrix_UB_23      0.0030906000
_diffrn_orient_matrix_UB_31      -0.0629483000
_diffrn_orient_matrix_UB_32      -0.0739619000
_diffrn_orient_matrix_UB_33      -0.0073662000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.813
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6583
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.726
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.861
_diffrn_reflns_theta_min         2.658
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
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    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1137 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3016
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0260
_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/[\s^2^(Fo^2^)+(0.0498P)^2^+0.0364P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0740
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    0.909
_reflns_Friedel_fraction_max     0.625
_reflns_number_gt                2895
_reflns_number_total             3016
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03881a2.cif
_cod_data_source_block           aysyn210531-2-293k_re
_cod_database_code               7130549
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.944
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C3(H3A,H3B), C1(H1A,H1B), C2(H2A,H2B), C11(H11A,
 H11B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              79682
_shelx_hkl_checksum              72110
_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 1.548
_oxdiff_exptl_absorpt_empirical_full_min 0.555