Synthesis, crystallographic analysis and Hirshfeld surface analysis of 4-bromo-2-{[2-(5-bromo-2-nitrophenyl)hydrazin-1-ylidene]methyl}-5-fluorophenol
Yaman, Mavise; Aydemir, Ercan; Dege, Necmi; Agar, Erbil; Iskenderov, Turganbay S.; Acta Crystallographica Section E 74 (2018) 1628–1632; doi:10.1107/S2056989018014627

data_2242683
_publ_section_title
;
 Synthesis, crystallographic analysis and Hirshfeld surface analysis of
 4-bromo-2-{[2-(5-bromo-2-nitrophenyl)hydrazin-1-ylidene]methyl}-5-fluorophenol
;
_journal_coeditor_code           XU5944
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1628
_journal_page_last               1632
_journal_paper_doi               10.1107/S2056989018014627
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C13 H8 Br2 F N3 O3'
_chemical_formula_moiety         'C13 H8 Br2 F N3 O3'
_chemical_formula_sum            'C13 H8 Br2 F N3 O3'
_chemical_formula_weight         433.04
_chemical_name_systematic
;
4-Bromo-2-{[2-(5-bromo-2-nitrophenyl)hydrazin-1-ylidene]methyl}-5-fluorophenol
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 95.026(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1360(14)
_cell_length_b                   4.1745(3)
_cell_length_c                   21.468(2)
_cell_measurement_reflns_used    5914
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.68
_cell_measurement_theta_min      1.52
_cell_volume                     1440.5(2)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-RED (Stoe & Cie, 2002)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1133
_diffrn_reflns_av_unetI/netI     0.1218
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9546
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         1.517
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    5.654
_exptl_absorpt_correction_T_max  0.8833
_exptl_absorpt_correction_T_min  0.2959
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe & Cie, 2002)
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.997
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.282
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.839
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.839
_refine_ls_R_factor_all          0.1306
_refine_ls_R_factor_gt           0.0506
_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^)+(0.0267P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0980
_reflns_number_gt                1270
_reflns_number_total             2775
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            xu5944sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
;
 The '_cell_lenght_a' data item was moved out of a data loop.

 Antanas Vaitkus,
 2019-08-21
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_cod_database_code               2242683
_cod_database_fobs_code          2242683
_shelx_hkl_checksum              81849
_shelx_res_checksum              78877