The six-membered-ring azomethine <i>N</i>-((<i>E</i>)-{5-[(<i>E</i>)-(pyridin-3-ylimino)methyl]thiophen-2-yl}methylidene)pyridin-3-amine
Bolduc, Andréanne; Dufresne, Stéphane; Skene, W. G.; Acta Crystallographica Section C 69 (2013) 1196–1199; doi:10.1107/S0108270113024566

data_2019188
_publ_section_title
;
 The six-membered-ring azomethine
 <i>N</i>-((<i>E</i>)-{5-[(<i>E</i>)-(pyridin-3-ylimino)methyl]thiophen-2-yl}methylidene)pyridin-3-amine
;
_journal_coeditor_code           LG3122
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1196
_journal_page_last               1199
_journal_paper_doi               10.1107/S0108270113024566
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C16 H12 N4 S'
_chemical_formula_moiety         'C16 H12 N4 S'
_chemical_formula_sum            'C16 H12 N4 S'
_chemical_formula_weight         292.36
_chemical_name_systematic
<i>N</i>-((<i>E</i>)-{5-[(<i>E</i>)-(Pyridin-3-ylimino)methyl]thiophen-2-yl}methylidene)pyridin-3-amine
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 108.0340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.4368(5)
_cell_length_b                   6.04900(10)
_cell_length_c                   14.6066(2)
_cell_measurement_reflns_used    9039
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.07
_cell_measurement_theta_min      2.78
_cell_volume                     2809.18(8)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
'SHELXTL (Bruker, 2001) and ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART 6000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18280
_diffrn_reflns_theta_full        26.09
_diffrn_reflns_theta_max         26.09
_diffrn_reflns_theta_min         1.28
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.323
_refine_ls_extinction_coef       0.0082(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+1.3506P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0937
_reflns_number_gt                2581
_reflns_number_total             2773
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            lg3122.cif
_cod_data_source_block           I
_cod_original_cell_volume        2809.18(7)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2019188