#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/69/2236968.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2236968
loop_
_publ_author_name
'Bolduc, Andréanne'
'Knipping, Étienne'
'Skene, W. G.'
_publ_section_title
;
 2-[(E)-(Pyridin-2-ylmethylidene)amino]thiophene-3-carbonitrile
;
_journal_coeditor_code           LX2267
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3262
_journal_paper_doi               10.1107/S1600536812043188
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H7 N3 S'
_chemical_formula_moiety         'C11 H7 N3 S'
_chemical_formula_sum            'C11 H7 N3 S'
_chemical_formula_weight         213.26
_chemical_name_systematic
;
2-[(E)-(Pyridin-2-ylmethylidene)amino]thiophene-3-carbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 94.9520(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.84510(10)
_cell_length_b                   20.8901(4)
_cell_length_c                   12.2725(2)
_cell_measurement_reflns_used    8225
_cell_measurement_temperature    296
_cell_measurement_theta_max      72.24
_cell_measurement_theta_min      4.19
_cell_volume                     982.10(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2  (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'UdMX (Marris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART 6000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13010
_diffrn_reflns_theta_full        72.55
_diffrn_reflns_theta_max         72.55
_diffrn_reflns_theta_min         4.19
_exptl_absorpt_coefficient_mu    2.640
_exptl_absorpt_correction_T_max  0.7095
_exptl_absorpt_correction_T_min  0.6369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.242
_refine_ls_extinction_coef       0.0048(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1940
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0354
_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/[σ²(Fo²)+(0.0705P)²+0.1553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                1777
_reflns_number_total             1940
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lx2267.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236968
_cod_database_fobs_code          2236968
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.28514(9) 0.585396(16) 0.49120(3) 0.03295(17) Uani d . 1 1
N N4 0.3288(3) 0.55247(5) 0.27296(10) 0.0300(3) Uani d . 1 1
N N6 -0.0323(3) 0.39582(6) 0.24657(11) 0.0355(3) Uani d . 1 1
N N11 0.6852(4) 0.70387(7) 0.16200(12) 0.0479(4) Uani d . 1 1
C C1 0.4195(4) 0.66118(7) 0.52750(12) 0.0351(3) Uani d . 1 1
H H1 0.4165 0.6777 0.5978 0.042 Uiso calc R 1 1
C C2 0.5305(4) 0.69438(7) 0.44255(12) 0.0330(3) Uani d . 1 1
H H2 0.6126 0.7362 0.4479 0.040 Uiso calc R 1 1
C C3 0.5078(4) 0.65807(6) 0.34397(12) 0.0296(3) Uani d . 1 1
C C4 0.3787(3) 0.59711(6) 0.35650(12) 0.0284(3) Uani d . 1 1
C C5 0.1810(4) 0.49926(7) 0.29216(12) 0.0307(3) Uani d . 1 1
H H5 0.1096 0.4923 0.3617 0.037 Uiso calc R 1 1
C C6 0.1192(4) 0.44890(7) 0.20990(12) 0.0299(3) Uani d . 1 1
C C7 0.2076(4) 0.45613(7) 0.10312(12) 0.0331(3) Uani d . 1 1
H H7 0.3145 0.4934 0.0816 0.040 Uiso calc R 1 1
C C8 0.1335(4) 0.40665(7) 0.02923(14) 0.0376(4) Uani d . 1 1
H H8 0.1885 0.4101 -0.0429 0.045 Uiso calc R 1 1
C C9 -0.0248(4) 0.35197(7) 0.06573(14) 0.0375(4) Uani d . 1 1
H H9 -0.0810 0.3182 0.0181 0.045 Uiso calc R 1 1
C C10 -0.0979(4) 0.34840(7) 0.17395(14) 0.0387(4) Uani d . 1 1
H H10 -0.1983 0.3110 0.1978 0.046 Uiso calc R 1 1
C C11 0.6052(4) 0.68224(7) 0.24209(13) 0.0343(3) Uani d . 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0387(2) 0.0311(2) 0.0296(2) -0.00353(13) 0.00597(16) 0.00229(12)
N4 0.0314(6) 0.0272(6) 0.0315(6) -0.0004(4) 0.0028(5) 0.0014(5)
N6 0.0401(7) 0.0303(6) 0.0359(7) -0.0054(5) 0.0016(5) 0.0021(5)
N11 0.0656(10) 0.0385(8) 0.0412(8) -0.0017(7) 0.0133(7) 0.0070(6)
C1 0.0394(8) 0.0340(8) 0.0323(8) -0.0001(6) 0.0043(6) -0.0036(6)
C2 0.0349(7) 0.0276(7) 0.0364(8) -0.0010(5) 0.0025(6) -0.0020(5)
C3 0.0306(7) 0.0262(7) 0.0319(7) 0.0005(5) 0.0026(5) 0.0021(5)
C4 0.0272(7) 0.0271(7) 0.0309(7) 0.0011(5) 0.0022(5) 0.0024(5)
C5 0.0334(7) 0.0291(7) 0.0295(7) -0.0016(5) 0.0024(5) 0.0027(5)
C6 0.0283(6) 0.0273(7) 0.0337(7) 0.0009(5) -0.0001(5) 0.0025(5)
C7 0.0353(7) 0.0286(7) 0.0357(7) 0.0010(5) 0.0048(6) 0.0015(6)
C8 0.0414(8) 0.0360(8) 0.0357(8) 0.0056(6) 0.0053(6) -0.0019(6)
C9 0.0370(8) 0.0303(8) 0.0444(9) 0.0033(6) -0.0013(6) -0.0068(6)
C10 0.0424(8) 0.0279(7) 0.0452(9) -0.0053(6) -0.0004(7) 0.0005(6)
C11 0.0402(8) 0.0256(7) 0.0374(8) -0.0011(6) 0.0048(6) 0.0009(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S1 C4 91.99(7)
C5 N4 C4 118.89(12)
C10 N6 C6 116.58(13)
C2 C1 S1 112.46(11)
C2 C1 H1 123.8
S1 C1 H1 123.8
C1 C2 C3 112.43(13)
C1 C2 H2 123.8
C3 C2 H2 123.8
C4 C3 C2 113.14(13)
C4 C3 C11 123.22(13)
C2 C3 C11 123.64(13)
C3 C4 N4 124.48(13)
C3 C4 S1 109.97(11)
N4 C4 S1 125.54(10)
N4 C5 C6 123.08(13)
N4 C5 H5 118.5
C6 C5 H5 118.5
N6 C6 C7 123.51(13)
N6 C6 C5 114.22(13)
C7 C6 C5 122.26(13)
C8 C7 C6 118.79(14)
C8 C7 H7 120.6
C6 C7 H7 120.6
C9 C8 C7 118.26(15)
C9 C8 H8 120.9
C7 C8 H8 120.9
C10 C9 C8 119.06(14)
C10 C9 H9 120.5
C8 C9 H9 120.5
N6 C10 C9 123.78(14)
N6 C10 H10 118.1
C9 C10 H10 118.1
N11 C11 C3 177.44(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7122(15)
S1 C4 1.7392(15)
N4 C5 1.2795(18)
N4 C4 1.3869(18)
N6 C10 1.342(2)
N6 C6 1.3478(19)
N11 C11 1.147(2)
C1 C2 1.352(2)
C1 H1 0.9300
C2 C3 1.424(2)
C2 H2 0.9300
C3 C4 1.3802(19)
C3 C11 1.428(2)
C5 C6 1.463(2)
C5 H5 0.9300
C6 C7 1.390(2)
C7 C8 1.388(2)
C7 H7 0.9300
C8 C9 1.387(2)
C8 H8 0.9300
C9 C10 1.383(2)
C9 H9 0.9300
C10 H10 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C4 S1 C1 C2 0.03(12)
S1 C1 C2 C3 0.06(17)
C1 C2 C3 C4 -0.15(19)
C1 C2 C3 C11 179.33(13)
C2 C3 C4 N4 179.51(12)
C11 C3 C4 N4 0.0(2)
C2 C3 C4 S1 0.17(16)
C11 C3 C4 S1 -179.31(11)
C5 N4 C4 C3 -174.38(13)
C5 N4 C4 S1 4.86(19)
C1 S1 C4 C3 -0.12(11)
C1 S1 C4 N4 -179.45(12)
C4 N4 C5 C6 -179.46(12)
C10 N6 C6 C7 -0.1(2)
C10 N6 C6 C5 179.36(13)
N4 C5 C6 N6 178.52(13)
N4 C5 C6 C7 -2.0(2)
N6 C6 C7 C8 0.8(2)
C5 C6 C7 C8 -178.60(13)
C6 C7 C8 C9 -0.3(2)
C7 C8 C9 C10 -0.9(2)
C6 N6 C10 C9 -1.2(2)
C8 C9 C10 N6 1.7(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658243
