Crystal structure and Hirshfeld surface analysis of 4-{2,2-dichloro-1-[(<i>E</i>)-(4-fluorophenyl)diazenyl]ethenyl}-<i>N</i>,<i>N</i>-dimethylaniline
Özkaraca, Kadriye; Akkurt, Mehmet; Shikhaliyev, Namiq Q.; Askerova, Ulviyya F.; Suleymanova, Gulnar T.; Shikhaliyeva, Irada M.; Bhattarai, Ajaya; Acta Crystallographica Section E 76 (2020) 811–815; doi:10.1107/S2056989020006106

data_2243386
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 4-{2,2-dichloro-1-[(<i>E</i>)-(4-fluorophenyl)diazenyl]ethenyl}-<i>N</i>,<i>N</i>-dimethylaniline
;
_journal_coeditor_code           VM2232
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              811
_journal_page_last               815
_journal_paper_doi               10.1107/S2056989020006106
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C16 H14 Cl2 F N3'
_chemical_formula_moiety         'C16 H14 Cl2 F N3'
_chemical_formula_sum            'C16 H14 Cl2 F N3'
_chemical_formula_weight         338.20
_chemical_name_systematic
4-{2,2-Dichloro-1-[(<i>E</i>)-(4-fluorophenyl)diazenyl]ethenyl}-<i>N</i>,<i>N</i>-dimethylaniline
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0730(3)
_cell_length_b                   15.9782(9)
_cell_length_c                   16.3860(7)
_cell_measurement_reflns_used    6056
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.79
_cell_volume                     1590.03(14)
_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)
;
_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      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.986
_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  0.0364
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12082
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.376
_diffrn_reflns_theta_min         2.486
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.417
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2003)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.224
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1002 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0431P)^2^+0.1514P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0844
_reflns_number_gt                2696
_reflns_number_total             3215
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            vm2232sup1.cif
_cod_data_source_block           I
_cod_database_code               2243386
_cod_database_fobs_code          2243386
_shelx_estimated_absorpt_t_min   0.896
_shelx_estimated_absorpt_t_max   0.932
_shelx_hkl_checksum              69600
_shelx_res_checksum              76627