Crystal structure and Hirshfeld surface analysis of (<i>E</i>)-1-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]-2-(4-fluorophenyl)diazene
Atioğlu, Zeliha; Akkurt, Mehmet; Shikhaliyev, Namiq Q.; Suleymanova, Gulnar T.; Bagirova, Khanim N.; Toze, Flavien A. A.; Acta Crystallographica Section E 75 (2019) 237–241; doi:10.1107/S2056989019000707

data_2242828
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (<i>E</i>)-1-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]-2-(4-fluorophenyl)diazene
;
_journal_coeditor_code           RZ5248
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              237
_journal_page_last               241
_journal_paper_doi               10.1107/S2056989019000707
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C14 H8 Cl2 F N3 O2'
_chemical_formula_moiety         'C14 H8 Cl2 F N3 O2'
_chemical_formula_sum            'C14 H8 Cl2 F N3 O2'
_chemical_formula_weight         340.13
_chemical_name_systematic
;
(<i>E</i>)-1-[2,2-Dichloro-1-(4-nitrophenyl)ethenyl]-2-(4-fluorophenyl)diazene
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 97.038(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8644(5)
_cell_length_b                   7.2242(2)
_cell_length_c                   12.7595(4)
_cell_measurement_reflns_used    4877
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.93
_cell_measurement_theta_min      3.10
_cell_volume                     1451.32(8)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX3 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2016 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11383
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.035
_diffrn_reflns_theta_min         3.217
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2003)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0427P)^2^+0.3915P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0885
_reflns_number_gt                2359
_reflns_number_total             2851
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            rz5248sup1.cif
_cod_data_source_block           I
_cod_database_code               2242828
_cod_database_fobs_code          2242828
_shelx_estimated_absorpt_t_min   0.857
_shelx_estimated_absorpt_t_max   0.937
_shelx_hkl_checksum              8008
_shelx_res_checksum              64843