Above Room Temperature Organic Ferroelectrics: Diprotonated 1,4-Diazabicyclo[2.2.2]octane Shifts between Two 2-Chlorobenzoates.
Yao, Zi-Shuo; Yamamoto, Kaoru; Cai, Hong-Ling; Takahashi, Kazuyuki; Sato, Osamu; Journal of the American Chemical Society 138 (2016) 12005–12008; doi:10.1021/jacs.6b03747

data_4125233
_publ_section_title
;
 Above Room Temperature Organic Ferroelectrics: Diprotonated
 1,4-Diazabicyclo[2.2.2]octane Shifts between Two 2-Chlorobenzoates.
;
_journal_issue                   37
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12005
_journal_page_last               12008
_journal_paper_doi               10.1021/jacs.6b03747
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C20 H22 Cl2 N2 O4'
_chemical_formula_weight         425.29
_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'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.745(5)
_cell_length_b                   11.357(3)
_cell_length_c                   8.8960(19)
_cell_measurement_reflns_used    5447
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      30.6790
_cell_measurement_theta_min      2.0687
_cell_volume                     1994.9(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Sir 2008'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
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_diffrn_reflns_point_group_measured_fraction_full 0.773
_diffrn_reflns_point_group_measured_fraction_max 0.750
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.497
_diffrn_reflns_theta_min         2.069
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.355
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8657
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       Prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 891 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.069(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3108
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0325
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.415
_reflns_Friedel_fraction_full    0.521
_reflns_Friedel_fraction_max     0.472
_reflns_number_gt                3079
_reflns_number_total             3108
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b03747_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4125230--4125234.cif.
;
_cod_database_code               4125233
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           2013-4