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_4003998
_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 L
_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                 90.602(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1224(2)
_cell_length_b                   12.0569(3)
_cell_length_c                   13.3229(4)
_cell_measurement_reflns_used    6407
_cell_measurement_temperature    173.1(5)
_cell_measurement_theta_max      28.6720
_cell_measurement_theta_min      2.2120
_cell_volume                     1465.28(7)
_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      173.1(5)
_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 0.852
_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    -18.00  34.00   0.50    2.00    --  -21.44 -99.00  90.00  104
  2  \w     -6.00  20.00   0.50    2.00    --  -21.44 -99.00 120.00   52
  3  \w    -16.00  36.00   0.50    2.00    --  -21.44 -99.00   0.00  104
  4  \w     -3.00  23.00   0.50    2.00    --  -21.44 -99.00 -60.00   52
  5  \w    -57.00  -9.00   0.50    2.00    --   21.44 -40.00-175.00   96
  6  \w    -37.00  98.00   0.50    2.00    --   21.44  40.00 -21.00  270
;
_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      0.0754662000
_diffrn_orient_matrix_UB_12      0.0048636000
_diffrn_orient_matrix_UB_13      -0.0114661000
_diffrn_orient_matrix_UB_21      -0.0183441000
_diffrn_orient_matrix_UB_22      0.0295171000
_diffrn_orient_matrix_UB_23      -0.0444481000
_diffrn_orient_matrix_UB_31      0.0033814000
_diffrn_orient_matrix_UB_32      0.0506432000
_diffrn_orient_matrix_UB_33      0.0270215000
_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  0.0517
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8323
_diffrn_reflns_point_group_measured_fraction_full 0.865
_diffrn_reflns_point_group_measured_fraction_max 0.710
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.150
_diffrn_reflns_theta_min         2.233
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67292
_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    1.362
_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         0.440
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1799 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5614
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0661P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1079
_reflns_Friedel_coverage         0.593
_reflns_Friedel_fraction_full    0.716
_reflns_Friedel_fraction_max     0.553
_reflns_number_gt                5097
_reflns_number_total             5614
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cm1c01663_si_004.cif
_cod_data_source_block           hcr_210315_2_173k
_cod_database_code               4003998
_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 99.91
_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.a Ternary CH refined with riding coordinates:
 C14(H14), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C20(H20A,H20B), C12(H12A,H12B), C3(H3A,H3B), C10(H10A,H10B),
 C17(H17A,H17B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4A), N2(H2), N1(H1), N3(H3), C23(H23), C21(H21), C24(H24), C22(H22),
 C26(H26), C25(H25)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              38508
_shelx_hkl_checksum              19399
_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 4.759
_oxdiff_exptl_absorpt_empirical_full_min 0.170