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_7250357
_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_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           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-19
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-11-25 deposited with the CCDC.	2025-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.605(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.1482(5)
_cell_length_b                   4.7544(2)
_cell_length_c                   11.9871(8)
_cell_measurement_reflns_used    3623
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      33.4270
_cell_measurement_theta_min      2.0090
_cell_volume                     577.76(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.975
_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   -120.00  60.00   1.00    1.00    --  -30.00  45.00   0.00  180
  2  \w   -120.00  30.00   1.00    1.00    --  -30.00  45.00  90.00  150
  3  \w   -120.00   0.00   1.00    1.00    --  -30.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0651449000
_diffrn_orient_matrix_UB_12      0.0544780000
_diffrn_orient_matrix_UB_13      -0.0016743000
_diffrn_orient_matrix_UB_21      -0.0254351000
_diffrn_orient_matrix_UB_22      -0.1374768000
_diffrn_orient_matrix_UB_23      -0.0090954000
_diffrn_orient_matrix_UB_31      -0.0025475000
_diffrn_orient_matrix_UB_32      -0.0197576000
_diffrn_orient_matrix_UB_33      0.0584946000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4215
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.009
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       0.084(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.391
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1142
_refine_ls_number_restraints     211
_refine_ls_restrained_S_all      1.289
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0537
_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^)+3.4936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1085
_reflns_number_total             1142
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00057b2.cif
_cod_data_source_block           r20221118a
_cod_depositor_comments
'Adding full bibliography for 7250356--7250358.cif.'
_cod_database_code               7250357
_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   0.602
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1-H1
 0.85 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Br1 \\sim Cl1 \\sim O1 \\sim N1 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5
\\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(Br1) \\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(N1)
\\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq,
Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim
Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: H1(0.5) Br1(0.5) Cl1(0.5) O1(0.5) N1(0.5) C5(0.5) H5(0.5) C4(0.5)
 C3(0.5) H3(0.5) C2(0.5) H2(0.5) C1(0.5) C6(0.5) H6(0.5) C7(0.5) H7(0.5)
 C9(0.5) H9(0.5) C8(0.5) C13(0.5) C12(0.5) H12(0.5) C11(0.5) C10(0.5) H10(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C2(H2), C6(H6), C7(H7), C9(H9), C12(H12), C10(H10)
5.b Fitted hexagon refined as free rotating group:
 C5(C4,C3,C2,C1,C6), C9(C8,C13,C12,C11,C10)
;
_shelx_res_checksum              38027
_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 1.655
_oxdiff_exptl_absorpt_empirical_full_min 0.730