Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(<i>E</i>)-(2-phenylhydrazinylidene)methyl]quinoline
Akhramez, Soufiane; Hafid, Abderrafia; Khouili, Mostafa; Saadi, Mohamed; El Ammari, Lahcen; Ketatni, El Mostafa; Acta Crystallographica Section E 75 (2019) 964–968; doi:10.1107/S2056989019007692

data_2242975
_publ_section_title
;
 Synthesis, crystal structure and Hirshfeld surface analysis of
 2-chloro-3-[(<i>E</i>)-(2-phenylhydrazinylidene)methyl]quinoline
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              964
_journal_page_last               968
_journal_paper_doi               10.1107/S2056989019007692
_journal_volume                  75
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C16 H12 Cl N3'
_chemical_formula_moiety         'C16 H12 Cl N3'
_chemical_formula_sum            'C16 H12 Cl N3'
_chemical_formula_weight         281.74
_chemical_name_systematic
;
2-Chloro-3-[(<i>E</i>)-(2-phenylhydrazinylidene)methyl]quinoline
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.883(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2114(4)
_cell_length_b                   19.4553(11)
_cell_length_c                   11.2520(7)
_cell_measurement_reflns_used    2981
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.102
_cell_measurement_theta_min      2.769
_cell_volume                     1359.01(14)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2016)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae <i>et al.</i>,
2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF
(Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'PHOTON100 CMOS area-detector'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE Super DUO'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'HELIOS mirror optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21613
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.769
_diffrn_source                   'INCOATEC I\mS micro-focus source'
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.141
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1200 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.023(15)
_refine_ls_extinction_coef       0.0046(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
(SHELXL2014; Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0293
_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^)+(0.0402P)^2^+0.2303P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0719
_reflns_number_gt                2712
_reflns_number_total             2981
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            su5497sup1.cif
_cod_data_source_block           I
_cod_database_code               2242975
_cod_database_fobs_code          2242975
_shelx_hkl_checksum              99196
_shelx_res_checksum              80069