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_2312412
_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          'C17 H14 Cl2 N2 O2'
_chemical_formula_moiety         'C17 H14 Cl2 N2 O2'
_chemical_formula_sum            'C17 H14 Cl2 N2 O2'
_chemical_formula_weight         349.20
_chemical_name_systematic
;
Methyl 4-{2,2-dichloro-1-[(<i>E</i>)-(4-methylphenyl)diazenyl]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                 109.6555(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6177(2)
_cell_length_b                   8.47502(11)
_cell_length_c                   13.10365(17)
_cell_measurement_reflns_used    12932
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.98
_cell_measurement_theta_min      2.96
_cell_volume                     1633.34(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>SHELXL</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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  0.0539
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28857
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.024
_diffrn_reflns_theta_min         3.005
_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    3.666
_exptl_absorpt_correction_T_max  0.530
_exptl_absorpt_correction_T_min  0.307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.481
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2018/3 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0579P)^2^+0.7484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                3197
_reflns_number_total             3469
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5708.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2312412
_shelx_estimated_absorpt_t_min   0.449
_shelx_estimated_absorpt_t_max   0.575
_shelx_hkl_checksum              177
_shelx_res_checksum              51018