Crystal structures and Hirshfeld surface analyses of (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-phenyldiazene, (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methylphenyl)diazene, (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methoxyphenyl)diazene and (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(3-methylphenyl)diazene
Maharramov, Abel; Shikhaliyev, Namiq Q.; Qajar, Ayten; Atakishiyeva, Gulnar T.; Niyazova, Ayten; Khrustalev, Victor N.; Akkurt, Mehmet; Yıldırım, Sema Öztürk; Bhattarai, Ajaya; Acta Crystallographica Section E Crystallographic Communications 79 (2023) –; doi:10.1107/S205698902300511X

data_2022791
_publ_section_title
;
 Crystal structures and Hirshfeld surface analyses of
 (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-phenyldiazene,
 (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methylphenyl)diazene,
 (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methoxyphenyl)diazene
 and
 (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(3-methylphenyl)diazene
;
_journal_coeditor_code           WM5684
_journal_issue                   7
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S205698902300511X
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C19 H20 Cl2 N2'
_chemical_formula_moiety         'C19 H20 Cl2 N2'
_chemical_formula_sum            'C19 H20 Cl2 N2'
_chemical_formula_weight         347.27
_chemical_name_systematic
;
(<i>E</i>)-1-[1-(4-<i>tert</i>-Butylphenyl)-2,2-dichloroethenyl]-2-\
(4-methylphenyl)diazene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 127.223(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.9062(6)
_cell_length_b                   6.27248(5)
_cell_length_c                   23.3475(4)
_cell_measurement_reflns_used    19033
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.14
_cell_measurement_theta_min      3.56
_cell_volume                     3604.08(17)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2021)
;
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            28692
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.530
_diffrn_reflns_theta_min         3.592
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.229
_exptl_absorpt_correction_T_max  0.630
_exptl_absorpt_correction_T_min  0.464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>CrysAlisPro</i>; Rigaku OD, 2021)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       prism
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.301
_refine_ls_extinction_coef       0.00017(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
<i>SHELXL2016/6</i> (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0470P)^2^+2.8000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0903
_reflns_number_gt                3643
_reflns_number_total             3805
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5684sup1.cif
_cod_data_source_block           II
_cod_original_cell_volume        3604.08(15)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2022791
_shelx_estimated_absorpt_t_min   0.579
_shelx_estimated_absorpt_t_max   0.661
_shelx_hkl_checksum              11405
_shelx_res_checksum              72548
_cod_database_fobs_code 2022791