Organic Enantiomeric Ferroelectrics with High Piezoelectric Performance: Imidazolium l- and d-Camphorsulfonate
Xu, Lei; Mu, Xin; Chen, Xiao-Gang; Zhang, Han-Yue; Xiong, Ren-Gen; Chemistry of Materials  (2021) –; doi:10.1021/acs.chemmater.1c01663

data_4003995
_publ_section_title
;
 Organic Enantiomeric Ferroelectrics with High Piezoelectric Performance:
 Imidazolium l- and d-Camphorsulfonate
;
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/acs.chemmater.1c01663
_journal_year                    2021
_chemical_absolute_configuration D
_chemical_formula_moiety         'C10 H15 O4 S, C3 H5 N2'
_chemical_formula_sum            'C13 H20 N2 O4 S'
_chemical_formula_weight         300.37
_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             2021-04-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.651(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1142(4)
_cell_length_b                   12.0574(5)
_cell_length_c                   13.2549(7)
_cell_measurement_reflns_used    6534
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      29.1050
_cell_measurement_theta_min      1.6220
_cell_volume                     1456.53(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.849
_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    -49.00  45.00   0.50    1.00    --   21.44 -59.00  85.00  188
  2  \w      3.00  92.00   0.50    1.00    --   21.44  59.00-134.00  178
  3  \w     52.00 101.00   0.50    1.00    --   21.44 178.00 120.00   98
  4  \w    -18.00   7.00   0.50    1.00    --  -21.44 -99.00   0.00   50
  5  \w    -13.00  32.00   0.50    1.00    --  -21.44 -99.00 -90.00   90
  6  \w    -15.00  12.00   0.50    1.00    --  -21.44 -99.00-120.00   54
;
_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      0.0450921000
_diffrn_orient_matrix_UB_12      -0.0375084000
_diffrn_orient_matrix_UB_13      0.0275631000
_diffrn_orient_matrix_UB_21      -0.0338967000
_diffrn_orient_matrix_UB_22      0.0168919000
_diffrn_orient_matrix_UB_23      0.0453654000
_diffrn_orient_matrix_UB_31      -0.0536130000
_diffrn_orient_matrix_UB_32      -0.0421459000
_diffrn_orient_matrix_UB_33      -0.0063200000
_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  0.0119
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8417
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.757
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.187
_diffrn_reflns_theta_min         1.536
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.506
_refine_diff_density_min         -0.929
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Flack x determined using 2374 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(14)
_refine_ls_extinction_coef       0.021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5975
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0560
_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/[\s^2^(Fo^2^)+(0.0677P)^2^+2.6357P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1430
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.840
_reflns_Friedel_fraction_max     0.657
_reflns_number_gt                5872
_reflns_number_total             5975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm1c01663_si_001.cif
_cod_data_source_block           xl20320_1_173k
_cod_database_code               4003995
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.954
_reflns_odcompleteness_completeness 99.97
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C15) = Uanis(C11) = Uanis(C14) = Uanis(C8)
Uanis(C7) = Uanis(C8) = Uanis(C12) = Uanis(C13)
3.a Ternary CH refined with riding coordinates:
 C20(H20), C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C25(H25A,H25B), C23(H23A,H23B), C9(H9A,H9B), C16(H16A,H16B),
 C19(H19A,H19B), C13(H13A,H13B), C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N1(H1), N2(H2), N4(H4), C1(H1A), C3(H3A), C2(H2A), C6(H6), C5(H5),
 C4(H4A)
3.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C00X(H00A,H00B,H00C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
_shelx_res_checksum              96999
_shelx_hkl_checksum              45573
_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 1.609
_oxdiff_exptl_absorpt_empirical_full_min 0.782