Crystal structure and Hirshfeld surface analysis of (<i>E</i>)-1-[2,2-dichloro-1-(4-methylphenyl)ethenyl]-2-(4-methoxyphenyl)diazene
Shikhaliyev, Namiq Q.; Atioğlu, Zeliha; Akkurt, Mehmet; Qacar, Ayten M.; Askerov, Rizvan K.; Bhattarai, Ajaya; Acta Crystallographica Section E 77 (2021) 965–970; doi:10.1107/S2056989021008756

data_2243907
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (<i>E</i>)-1-[2,2-dichloro-1-(4-methylphenyl)ethenyl]-2-(4-methoxyphenyl)diazene
;
_journal_coeditor_code           ZN2009
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              965
_journal_page_last               970
_journal_paper_doi               10.1107/S2056989021008756
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C16 H14 Cl2 N2 O'
_chemical_formula_moiety         'C16 H14 Cl2 N2 O'
_chemical_formula_sum            'C16 H14 Cl2 N2 O'
_chemical_formula_weight         321.19
_chemical_name_systematic
(<i>E</i>)-1-[2,2-Dichloro-1-(4-methylphenyl)ethenyl]-2-(4-methoxyphenyl)diazene
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 99.173(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5366(3)
_cell_length_b                   17.9208(8)
_cell_length_c                   16.2085(8)
_cell_measurement_reflns_used    3046
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.26
_cell_measurement_theta_min      2.61
_cell_volume                     1587.65(14)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
<i>SHELXL2016/6</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2016/6</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0537
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19301
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.349
_diffrn_reflns_theta_min         1.706
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.316
_refine_ls_abs_structure_details
;
 Refined as an inversion twin
;
_refine_ls_abs_structure_Flack   0.11(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         6444
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0594
_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^)+(0.0481P)^2^+0.5767P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1449
_reflns_number_gt                3820
_reflns_number_total             6444
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            zn2009sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2243907
_shelx_estimated_absorpt_t_min   0.908
_shelx_estimated_absorpt_t_max   0.961
_shelx_hkl_checksum              30938
_shelx_res_checksum              45183
_cod_database_fobs_code 2243907