Ferroelectricity and switching polarization on the C–H⋯π bond in a pure organic molecular crystal – 1,3,5-trimethylnitrobenzene
Szklarz, Przemysław; Kinzhybalo, Vasyl; Bator, Grażyna; CrystEngComm 23 (2021) 4005–4012; doi:10.1039/D1CE00381J

data_7242728
_publ_section_title
;
 Ferroelectricity and switching polarization on the C--H&#x22EF;\p bond in
 a pure organic molecular crystal -- 1,3,5-trimethylnitrobenzene
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              4005
_journal_page_last               4012
_journal_paper_doi               10.1039/D1CE00381J
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C, C9 H11 N O2'
_chemical_formula_sum            'C9 H11 N O2'
_chemical_formula_weight         165.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2020-03-21 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.306(5)
_cell_length_b                   6.980(2)
_cell_length_c                   15.165(6)
_cell_measurement_reflns_used    7481
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      29.2640
_cell_measurement_theta_min      2.9750
_cell_volume                     1726.0(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.959
_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     32.00 104.00   1.00    4.00    --   13.60-178.00  90.00   72
  2  \w    -77.00 -32.00   1.00    4.00    --   13.60 178.00   0.00   45
  3  \w    -19.00  92.00   1.00    4.00    --   13.60  57.00  90.00  111
  4  \w    -64.00  46.00   1.00    4.00    --   13.60 -57.00 120.00  110
  5  \w     35.00 106.00   1.00    4.00    --   13.60 178.00 -30.00   71
  6  \w    -19.00  92.00   1.00    4.00    --   13.60  57.00-120.00  111
  7  \w    -50.00  11.00   1.00    4.00    --  -14.38  77.00 -60.00   61
  8  \w    -25.00  30.00   1.00    4.00    --  -14.38 -99.00 -60.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0214048000
_diffrn_orient_matrix_UB_12      0.0784922000
_diffrn_orient_matrix_UB_13      -0.0187552000
_diffrn_orient_matrix_UB_21      -0.0207323000
_diffrn_orient_matrix_UB_22      0.0635318000
_diffrn_orient_matrix_UB_23      0.0289373000
_diffrn_orient_matrix_UB_31      0.0316742000
_diffrn_orient_matrix_UB_32      -0.0113849000
_diffrn_orient_matrix_UB_33      0.0316174000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25698
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.332
_diffrn_reflns_theta_min         2.498
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.702
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.246
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1485 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.4(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4396
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0598P)^2^+0.4107P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1198
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.891
_reflns_number_gt                3554
_reflns_number_total             4396
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00381j3.cif
_cod_data_source_block           tmnb19_vt_37_100_00abs
_cod_depositor_comments
'Adding full bibliography for 7242727--7242728.cif.'
_cod_original_cell_volume        1725.9(10)
_cod_database_code               7242728
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C9 H11 N O2'
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: CGA(0) CGB(0)
3.a Everything fixed:
 CGA, CGB
3.b Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C6A(H6A), C4B(H4B), C6B(H6B)
3.c Idealised Me refined as rotating group:
 C7A(H7AA,H7AB,H7AC), C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC), C7B(H7BA,H7BB,
 H7BC), C8B(H8BA,H8BB,H8BC), C9B(H9BA,H9BB,H9BC)
;
_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 1.177
_oxdiff_exptl_absorpt_empirical_full_min 0.906