(<i>E</i>)-3-{[(2-Bromo-3-methylphenyl)imino]methyl}benzene-1,2-diol: crystal structure and Hirshfeld surface analysis
Doğan, Onur Erman; Dege, Necmi; Ağar, Erbil; Fritsky, Igor O.; Acta Crystallographica Section E 75 (2019) 1930–1933; doi:10.1107/S2056989019015718

data_2243212
_publ_section_title
;
 (<i>E</i>)-3-{[(2-Bromo-3-methylphenyl)imino]methyl}benzene-1,2-diol:
 crystal structure and Hirshfeld surface analysis
;
_journal_coeditor_code           MW2151
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1930
_journal_page_last               1933
_journal_paper_doi               10.1107/S2056989019015718
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C14 H12 Br N O2'
_chemical_formula_moiety         'C14 H12 Br N O2'
_chemical_formula_sum            'C14 H12 Br N O2'
_chemical_formula_weight         306.16
_chemical_name_systematic
;
(<i>E</i>)-3-{[(2-Bromo-3-methylphenyl)imino]methyl}benzene-1,2-diol
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'intrinsic phasing'
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                102.496(5)
_cell_angle_beta                 90.597(5)
_cell_angle_gamma                103.213(5)
_cell_formula_units_Z            4
_cell_length_a                   8.2301(5)
_cell_length_b                   10.1593(6)
_cell_length_c                   15.9428(9)
_cell_measurement_reflns_used    15203
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.41
_cell_measurement_theta_min      2.11
_cell_volume                     1264.46(13)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2002)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
Mercury (Macrae <i>et al.</i>,  2006), WinGX (Farrugia, 2012)
and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXT2018 (Sheldrick, 2015a), SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
WinGX (Farrugia, 2012)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13105
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.113
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           45
_diffrn_source_power             2.25
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    3.243
_exptl_absorpt_correction_T_max  0.6626
_exptl_absorpt_correction_T_min  0.4414
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe & Cie, 2002)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_description       column
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.313
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0365P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0812
_reflns_number_gt                3352
_reflns_number_total             4958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            mw2151sup1.cif
_cod_data_source_block           I
_cod_database_code               2243212
_cod_database_fobs_code          2243212
_shelx_hkl_checksum              66926
_shelx_res_checksum              44191