Similar polymorphism of derivatives of salicylideneanilines with varying halo-substitution
Zhang, Zaixiang; Li, Xin; Liu, Junyu; Wang, Manman; Yang, Yang; Wang, Deyin; CrystEngComm 27 (2025) 3594–3604; doi:10.1039/D5CE00057B

data_7250358
_publ_section_title
;
 Similar polymorphism of derivatives of salicylideneanilines with varying
 halo-substitution
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              3594
_journal_page_last               3604
_journal_paper_doi               10.1039/D5CE00057B
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H9 Br Cl N O'
_chemical_formula_sum            'C13 H9 Br Cl N O'
_chemical_formula_weight         310.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2lqtw1
_audit_creation_date             2022-01-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-04-22 deposited with the CCDC.	2025-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.458(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.1919(5)
_cell_length_b                   4.7204(2)
_cell_length_c                   11.9836(6)
_cell_measurement_reflns_used    4563
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.6530
_cell_measurement_theta_min      2.0360
_cell_volume                     576.00(5)
_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_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.924
_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   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  35.00   1.00    1.00    --  -25.00  45.00  90.00  150
  3  \w   -115.00   5.00   1.00    1.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0056845000
_diffrn_orient_matrix_UB_12      0.1224850000
_diffrn_orient_matrix_UB_13      -0.0342060000
_diffrn_orient_matrix_UB_21      -0.0686768000
_diffrn_orient_matrix_UB_22      0.0025633000
_diffrn_orient_matrix_UB_23      0.0071807000
_diffrn_orient_matrix_UB_31      0.0100372000
_diffrn_orient_matrix_UB_32      0.0870312000
_diffrn_orient_matrix_UB_33      0.0478521000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6836
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.830
_diffrn_reflns_theta_min         3.403
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.780
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.227(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3495
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0478P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.700
_reflns_number_gt                3178
_reflns_number_total             3495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00057b2.cif
_cod_data_source_block           r20210819c
_cod_depositor_comments
'Adding full bibliography for 7250356--7250358.cif.'
_cod_database_code               7250358
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.704
_shelx_estimated_absorpt_t_min   0.583
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.773(14)
 0.227(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              95307
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.250
_oxdiff_exptl_absorpt_empirical_full_min 0.829