Crystal structures and Hirshfeld surface analyses of methyl 4-{2,2-di-chloro-1-[(<i>E</i>)-phenyl-diazen-yl]eth-enyl}benzoate, methyl 4-{2,2-di-chloro-1-[(<i>E</i>)-(4-methyl-phen-yl)diazen-yl]ethen-yl}benzoate and methyl 4-{2,2-di-chloro-1-[(<i>E</i>)-(3,4-di-methyl-phen-yl)diazen-yl]ethen-yl}benzoate.
Shikhaliyev, Namiq Q.; İbrahimova, Shafiga A; Atakishiyeva, Gulnar T.; Ahmedova, Nigar E.; Babayeva, Gulnara V.; Khrustalev, Victor N.; Atioğlu, Zeliha; Akkurt, Mehmet; Bhattarai, Ajaya; Acta crystallographica. Section E, Crystallographic communications 80 (2024) 184–190; doi:10.1107/S2056989024000732

data_2312411
_publ_section_title
;
 Crystal structures and Hirshfeld surface analyses of methyl
 4-{2,2-di-chloro-1-[(<i>E</i>)-phenyl-diazen-yl]eth-enyl}benzoate, methyl
 4-{2,2-di-chloro-1-[(<i>E</i>)-(4-methyl-phen-yl)diazen-yl]ethen-yl}benzoate
 and methyl
 4-{2,2-di-chloro-1-[(<i>E</i>)-(3,4-di-methyl-phen-yl)diazen-yl]ethen-yl}benzoate.
;
_journal_coeditor_code           WM5708
_journal_issue                   'Pt 2'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              184
_journal_page_last               190
_journal_paper_doi               10.1107/S2056989024000732
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C16 H12 Cl2 N2 O2'
_chemical_formula_moiety         'C16 H12 Cl2 N2 O2'
_chemical_formula_sum            'C16 H12 Cl2 N2 O2'
_chemical_formula_weight         335.18
_chemical_name_systematic
;
Methyl 4-{2,2-dichloro-1-[(<i>E</i>)-phenyldiazenyl]ethenyl}benzoate
;
_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                 100.1964(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.47572(16)
_cell_length_b                   4.16896(4)
_cell_length_c                   23.2257(2)
_cell_measurement_reflns_used    12282
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.0
_cell_measurement_theta_min      2.9
_cell_volume                     1474.80(2)
_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>SHELXL</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT</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  0.0603
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            23940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.805
_diffrn_reflns_theta_min         2.901
_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    4.036
_exptl_absorpt_correction_T_max  0.600
_exptl_absorpt_correction_T_min  0.404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.316
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0503P)^2^+1.3375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                2823
_reflns_number_total             3151
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5708.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2312411
_shelx_estimated_absorpt_t_min   0.470
_shelx_estimated_absorpt_t_max   0.665
_shelx_hkl_checksum              28337
_shelx_res_checksum              40683