Crystal structure and Hirshfeld surface analysis of 4-{2,2-dichloro-1-[(<i>E</i>)-(4-chlorophenyl)diazenyl]ethenyl}-<i>N</i>,<i>N</i>-dimethylaniline
Atioğlu, Zeliha; Akkurt, Mehmet; Shikhaliyev, Namiq Q.; Mukhtarova, Sevinc H.; Suleymanova, Gulnar T.; Toze, Flavien A. A.; Acta Crystallographica Section E 76 (2020) 1033–1037; doi:10.1107/S2056989020007549

data_2243430
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 4-{2,2-dichloro-1-[(<i>E</i>)-(4-chlorophenyl)diazenyl]ethenyl}-<i>N</i>,<i>N</i>-dimethylaniline
;
_journal_coeditor_code           WM5554
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1033
_journal_page_last               1037
_journal_paper_doi               10.1107/S2056989020007549
_journal_volume                  76
_journal_year                    2020
_chemical_formula_moiety         'C16 H14 Cl3 N3'
_chemical_formula_sum            'C16 H14 Cl3 N3'
_chemical_formula_weight         354.65
_chemical_name_systematic
4-{2,2-Dichloro-1-[(<i>E</i>)-(4-chlorophenyl)diazenyl]ethenyl}-<i>N</i>,<i>N</i>-dimethylaniline
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                92.338(2)
_cell_angle_beta                 91.212(2)
_cell_angle_gamma                94.048(2)
_cell_formula_units_Z            6
_cell_length_a                   9.7515(5)
_cell_length_b                   9.8203(5)
_cell_length_c                   26.6696(16)
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.55
_cell_measurement_theta_min      2.25
_cell_volume                     2544.7(2)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX3 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), <i>OLEX2</i> (Dolomanov <i>et
al.</i>,  2009)
;
_computing_publication_material
;
PLATON (Spek, 2020), publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII PHOTON 100 detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            40829
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.707
_diffrn_reflns_theta_min         2.294
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.539
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       plate
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.301
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     601
_refine_ls_number_reflns         9634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0500P)^2^+0.8216P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                6689
_reflns_number_total             9634
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5554sup1.cif
_cod_data_source_block           I
_cod_database_code               2243430
_cod_database_fobs_code          2243430
_shelx_estimated_absorpt_t_min   0.882
_shelx_estimated_absorpt_t_max   0.953
_shelx_hkl_checksum              23418
_shelx_res_checksum              89075