Crystal structure of 4-bromo-N′-[3,5-dichloro-2-hydroxyphenyl)methylidene]benzohydrazide methanol solvate, C15H13BrCl2N2O3
Xu, Xindi; Huang, Meifen; Wang, Man; Li, Tianyu; Wu, Qiong; Zeitschrift für Kristallographie - New Crystal Structures 236 (2021) 421–423; doi:10.1515/ncrs-2020-0597

data_8104849
_publ_section_title
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 Crystal structure of
 4-bromo-N&#x2032;-[3,5-dichloro-2-hydroxyphenyl)methylidene]benzohydrazide
 methanol solvate, C15H13BrCl2N2O3
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_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              421
_journal_page_last               423
_journal_paper_doi               10.1515/ncrs-2020-0597
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C14 H9 Br Cl2 N2 O2, C H4 O'
_chemical_formula_sum            'C15 H13 Br Cl2 N2 O3'
_chemical_formula_weight         420.07
_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   geom
_cell_angle_alpha                90
_cell_angle_beta                 104.445(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4135(4)
_cell_length_b                   13.3008(8)
_cell_length_c                   16.9956(7)
_cell_measurement_reflns_used    5019
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.11
_cell_measurement_theta_min      2.84
_cell_volume                     1622.88(15)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35252
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.408
_diffrn_reflns_theta_min         1.969
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.877
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0105
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
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SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0850 before and 0.0657 after correction.
The Ratio of minimum to maximum transmission is 0.3804.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0471P)^2^+1.3279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2507
_reflns_number_total             3323
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0597_suppl.cif
_cod_data_source_block           mo_0803_1_0m
_cod_database_code               8104849
_shelx_estimated_absorpt_t_max   0.625
_shelx_estimated_absorpt_t_min   0.570
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 N2, C7
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.005
 N1, C8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.005
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;