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_7251540
_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          424.0(10)
_chemical_name_systematic
N^1^,N^4^-bis[[2-(trifluoromethyl)phenyl]methylene]-1,4-benzenediamine
_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                 92.252(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.9998(10)
_cell_length_b                   12.277(2)
_cell_length_c                   14.928(3)
_cell_measurement_reflns_used    2322
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.26
_cell_measurement_theta_min      2.15
_cell_volume                     915.6(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    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens SMART platform CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10454
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_min         2.148
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS 2016/2 Krause et al., J. Appl. Cryst. 48 (2015) 3-10'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             428
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6634
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0500P)^2^+0.1281P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1012
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1612
_reflns_number_total             2109
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce01058f2.cif
_cod_data_source_block           09016z
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '423-425K' was changed to
'424.0(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               7251540
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.936
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              92610