Crystal structure and Hirshfeld surface analysis of (<i>E</i>)-1-(4-chlorophenyl)-2-[2,2-dichloro-1-(4-fluorophenyl)ethenyl]diazene
Shikhaliyev, Namiq Q.; Çelikesir, Sevim Türktekin; Akkurt, Mehmet; Bagirova, Khanim N.; Suleymanova, Gulnar T.; Toze, Flavien A. A.; Acta Crystallographica Section E 75 (2019) 465–469; doi:10.1107/S2056989019003657

data_2242878
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (<i>E</i>)-1-(4-chlorophenyl)-2-[2,2-dichloro-1-(4-fluorophenyl)ethenyl]diazene
;
_journal_coeditor_code           IS5510
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              465
_journal_page_last               469
_journal_paper_doi               10.1107/S2056989019003657
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C14 H8 Cl3 F N2'
_chemical_formula_moiety         'C14 H8 Cl3 F N2'
_chemical_formula_sum            'C14 H8 Cl3 F N2'
_chemical_formula_weight         329.57
_chemical_name_systematic
;
(<i>E</i>)-1-(4-Chlorophenyl)-2-[2,2-dichloro-1-(4-fluorophenyl)ethenyl]\
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     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 94.30(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8617(8)
_cell_length_b                   24.249(5)
_cell_length_c                   14.724(3)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      3.3
_cell_volume                     1374.9(5)
_computing_cell_refinement
;
<i>iMosflm</i> (Battye <i>et al.</i>,  2011)
;
_computing_data_collection
;
<i>Marccd</i> (Doyle, 2011)
;
_computing_data_reduction        <i>iMosflm</i>
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.80246
_diffrn_reflns_av_R_equivalents  0.1145
_diffrn_reflns_av_unetI/netI     0.0850
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20761
_diffrn_reflns_theta_full        28.782
_diffrn_reflns_theta_max         30.925
_diffrn_reflns_theta_min         3.248
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>Scala</i>; Evans, 2006)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.723
_refine_ls_extinction_coef       0.026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0557P)^2^+1.092P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1419
_reflns_number_gt                2719
_reflns_number_total             2984
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            is5510sup1.cif
_cod_data_source_block           I
_cod_database_code               2242878
_cod_database_fobs_code          2242878
_shelx_estimated_absorpt_t_min   0.834
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              8647
_shelxl_version_number           .2013