Examining the role of molecular and crystallographic symmetry in isomorphism: a series of centrosymmetric “bridge-flipped” trifluoromethyl-substituted bis-benzylideneanilines
Gerten, Anthony L.; Larson, Sarah N.; Ojala, William H.; CrystEngComm 28 (2026) 849–861; doi:10.1039/D5CE01058F

data_7251538
_publ_section_title
;
 Examining the role of molecular and crystallographic symmetry in
 isomorphism: a series of centrosymmetric &#x201C;bridge-flipped&#x201D;
 trifluoromethyl-substituted bis-benzylideneanilines
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              849
_journal_page_last               861
_journal_paper_doi               10.1039/D5CE01058F
_journal_volume                  28
_journal_year                    2026
_chemical_formula_sum            'C22 H14 F6 N2'
_chemical_formula_weight         420.35
_chemical_melting_point          404.0(10)
_chemical_name_systematic
N,N^'^-(1,4-phenylenedimethylidyne)bis(3-trifluoromethyl)benzenamine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-08-25 deposited with the CCDC.	2025-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.023(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.786(3)
_cell_length_b                   4.7478(10)
_cell_length_c                   14.494(3)
_cell_measurement_reflns_used    2990
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      2.83
_cell_volume                     875.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'Mercury (Macrae et al., J. Appl. Cryst., 53, 226-235, 2020)and ORTEP-3 for Windows (L. J. Farrugia, J. Appl. Cryst. (2012),45, 849-854)'
_computing_publication_material
'enCIFer (Allen et al., J. Appl. Cryst., 37, 335-338, 2004)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9477
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_min         2.022
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2012/1 (Sheldrick, 2012)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             428
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.110
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6972
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0452P)^2^+0.3384P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1699
_reflns_number_total             2010
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce01058f2.cif
_cod_data_source_block           15018z
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '403-405 K' was changed to
'404.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7251538
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              38306