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_7250356
_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 Br2 N O'
_chemical_formula_sum            'C13 H9 Br2 N O'
_chemical_formula_weight         355.03
_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.cc2lqtv0
_audit_creation_date             2024-10-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-04-22 deposited with the CCDC.	2025-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.026(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3111(3)
_cell_length_b                   4.75675(13)
_cell_length_c                   11.9502(4)
_cell_measurement_reflns_used    3260
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7180
_cell_measurement_theta_min      4.2780
_cell_volume                     585.76(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.970
_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    -30.00  -4.00   0.50    0.05    --  -58.46  45.00 -60.00   52
  2  \w    -57.00 -28.00   0.50    0.05    --  -77.79  63.00  30.00   58
  3  \w    -22.00   7.00   0.50    0.05    --  -51.68  45.00 150.00   58
  4  \w    -29.00   8.00   0.50    0.05    --  -51.68  45.00 -90.00   74
  5  \w    -52.00 -26.00   0.50    0.05    --  -77.79  63.00-180.00   52
  6  \w    -92.00 -40.00   0.50    0.05    --  -77.79 111.00-150.00  104
  7  \w    -90.00 -32.00   0.50    0.05    --  -82.00 101.00 -74.00  116
  8  \w   -133.00 -77.00   0.50    0.05    --  -77.79 -50.00  30.00  112
  9  \w   -112.00 -50.00   0.50    0.05    --  -51.68 -45.00 -30.00  124
 10  \w   -108.00 -29.00   0.50    0.05    --  -77.79 -12.00-150.00  158
 11  \w    114.00 151.00   0.50    0.05    --   93.74 111.00 -30.00   74
 12  \w     98.00 123.00   0.50    0.05    --   93.74 111.00   0.00   50
 13  \w     44.00  69.00   0.50    0.05    --   93.74 -77.00-120.00   50
 14  \w     44.00  69.00   0.50    0.05    --   93.74 -77.00 -90.00   50
 15  \w    103.00 134.00   0.50    0.05    --   93.74  50.00  90.00   62
 16  \w    103.00 138.00   0.50    0.05    --   93.74  77.00  90.00   70
 17  \w    114.00 145.00   0.50    0.05    --   93.74  50.00 -30.00   62
 18  \w    107.00 144.00   0.50    0.05    --   93.74  50.00   0.00   74
 19  \w     98.00 142.00   0.50    0.05    --   93.74  63.00 -60.00   88
 20  \w     99.00 124.00   0.50    0.05    --   93.74  77.00-120.00   50
 21  \w     99.00 141.00   0.50    0.05    --   93.74  77.00-150.00   84
 22  \w     41.00  85.00   0.50    0.05    --   93.74-111.00 -60.00   88
 23  \w     45.00  81.00   0.50    0.05    --   93.74 -91.00 -60.00   72
 24  \w     51.00  78.00   0.50    0.05    --   93.74 -91.00-120.00   54
 25  \w     40.00  65.00   0.50    0.05    --   93.74 -91.00-150.00   50
 26  \w     42.00  89.00   0.50    0.05    --   93.74 -91.00-180.00   94
 27  \w     61.00  91.00   0.50    0.05    --   93.74 -91.00  30.00   60
 28  \w     49.00  89.00   0.50    0.05    --   98.00 -91.00 153.48   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0283539000
_diffrn_orient_matrix_UB_12      0.0158828000
_diffrn_orient_matrix_UB_13      -0.1255882000
_diffrn_orient_matrix_UB_21      0.1463971000
_diffrn_orient_matrix_UB_22      0.0201414000
_diffrn_orient_matrix_UB_23      0.0292655000
_diffrn_orient_matrix_UB_31      0.0103818000
_diffrn_orient_matrix_UB_32      -0.3228178000
_diffrn_orient_matrix_UB_33      -0.0043952000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3298
_diffrn_reflns_point_group_measured_fraction_full 0.737
_diffrn_reflns_point_group_measured_fraction_max 0.702
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.840
_diffrn_reflns_theta_min         4.290
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)'
_exptl_crystal_density_diffrn    2.013
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.133
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.33(4)
_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     155
_refine_ls_number_reflns         1703
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0682P)^2^+0.5414P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0848
_reflns_Friedel_coverage         0.443
_reflns_Friedel_fraction_full    0.479
_reflns_Friedel_fraction_max     0.432
_reflns_number_gt                1700
_reflns_number_total             1703
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00057b2.cif
_cod_data_source_block           37-cr-20241011f_auto
_cod_depositor_comments
'Adding full bibliography for 7250356--7250358.cif.'
_cod_database_code               7250356
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOBr
_shelx_estimated_absorpt_t_max   0.400
_shelx_estimated_absorpt_t_min   0.231
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              24595
_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 3.341
_oxdiff_exptl_absorpt_empirical_full_min 0.581