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_2022792
_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 O'
_chemical_formula_moiety         'C19 H20 Cl2 N2 O'
_chemical_formula_sum            'C19 H20 Cl2 N2 O'
_chemical_formula_weight         363.27
_chemical_name_systematic
(<i>E</i>)-1-[1-(4-<i>tert</i>-Butylphenyl)-2,2-dichloroethenyl]-2-(4-methoxyphenyl)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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 112.5050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8738(2)
_cell_length_b                   12.5946(2)
_cell_length_c                   11.30130(10)
_cell_measurement_reflns_used    17727
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.55
_cell_measurement_theta_min      3.43
_cell_volume                     1824.35(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.986
_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  0.0758
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25894
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.878
_diffrn_reflns_theta_min         3.448
_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    3.256
_exptl_absorpt_correction_T_max  0.550
_exptl_absorpt_correction_T_min  0.431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>CrysAlisPro</i>; Rigaku OD, 2021)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.327
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0831P)^2^+0.4008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1179
_reflns_number_gt                3603
_reflns_number_total             3843
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5684sup1.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022792
_shelx_estimated_absorpt_t_min   0.509
_shelx_estimated_absorpt_t_max   0.592
_shelx_hkl_checksum              311
_shelx_res_checksum              3167
_cod_database_fobs_code 2022792