#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/60/2216045.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_2216045
loop_
_publ_author_name
'Guodong Yao'
'Shizhu Sun'
'Dacheng Li'
'Daqi Wang'
'Jianmin Dou'
_publ_section_title
;
 N'-[1-(2-Thienyl)ethylidene]pyridine-2-carbohydrazide
;
_journal_coeditor_code           LH2521
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4324
_journal_page_last               o4324
_journal_paper_doi               10.1107/S1600536807049811
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C12 H11 N3 O S'
_chemical_formula_moiety         'C12 H11 N3 O S'
_chemical_formula_sum            'C12 H11 N3 O S'
_chemical_formula_weight         245.30
_chemical_name_systematic
;
N'-[1-(2-Thienyl)ethylidene]pyridine-2-carbohydrazide
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.857(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.162(2)
_cell_length_b                   9.8259(16)
_cell_length_c                   10.2461(17)
_cell_measurement_reflns_used    2156
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.208
_cell_measurement_theta_min      2.702
_cell_volume                     1183.5(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5755
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.9451
_exptl_absorpt_correction_T_min  0.8682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.264
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2088
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      2.083
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0845P)²+0.601P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1541
_reflns_number_gt                1531
_reflns_number_total             2088
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2521.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1183.5(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2216045
_cod_database_fobs_code          2216045
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
N N1 0.1445(4) 0.8579(5) 0.0924(5) 0.0484(12) Uani d . 1
H H1 0.1133 0.8729 0.0084 0.058 Uiso calc RD 1
N N2 0.2426(4) 0.9265(4) 0.1575(4) 0.0447(11) Uani d . 1
N N3 -0.0534(4) 0.7579(5) -0.0438(4) 0.0482(12) Uani d . 1
O O1 0.1393(3) 0.7400(4) 0.2790(4) 0.0579(12) Uani d . 1
S S1 0.43434(14) 1.0654(2) 0.33637(15) 0.0677(7) Uani d . 1
C C1 0.0987(4) 0.7684(6) 0.1611(5) 0.0431(13) Uani d . 1
C C2 -0.0087(4) 0.7049(5) 0.0788(5) 0.0416(12) Uani d . 1
C C3 -0.0575(5) 0.5980(6) 0.1313(6) 0.0512(15) Uani d . 1
H H3 -0.0241 0.5642 0.2171 0.061 Uiso calc R 1
C C4 -0.1572(5) 0.5424(7) 0.0530(6) 0.0585(16) Uani d . 1
H H4 -0.1922 0.4701 0.0850 0.070 Uiso calc R 1
C C5 -0.2034(5) 0.5957(7) -0.0723(6) 0.0595(17) Uani d . 1
H H5 -0.2705 0.5604 -0.1269 0.071 Uiso calc R 1
C C6 -0.1494(5) 0.7020(7) -0.1162(6) 0.0568(16) Uani d . 1
H H6 -0.1817 0.7372 -0.2017 0.068 Uiso calc R 1
C C7 0.2513(5) 1.0330(7) -0.0622(6) 0.0583(16) Uani d . 1
H H7A 0.1828 0.9830 -0.1004 0.087 Uiso calc RD 1
H H7B 0.3093 1.0058 -0.1051 0.087 Uiso calc R 1
H H7C 0.2368 1.1286 -0.0761 0.087 Uiso calc R 1
C C8 0.2906(4) 1.0040(5) 0.0875(5) 0.0414(12) Uani d . 1
C C9 0.3943(4) 1.0717(5) 0.1632(5) 0.0426(13) Uani d . 1
C C10 0.4717(5) 1.1431(7) 0.1159(6) 0.0607(17) Uani d . 1
H H10 0.4650 1.1585 0.0247 0.073 Uiso calc R 1
C C11 0.5637(5) 1.1916(7) 0.2204(7) 0.0663(18) Uani d . 1
H H11 0.6242 1.2413 0.2049 0.080 Uiso calc R 1
C C12 0.5543(5) 1.1585(7) 0.3430(7) 0.0596(17) Uani d . 1
H H12 0.6068 1.1831 0.4227 0.071 Uiso calc R 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
N1 0.040(2) 0.055(3) 0.044(2) -0.009(2) -0.0010(19) 0.006(2)
N2 0.035(2) 0.048(3) 0.046(3) -0.004(2) 0.0006(19) 0.003(2)
N3 0.041(3) 0.054(3) 0.047(3) -0.004(2) 0.007(2) 0.000(2)
O1 0.052(2) 0.070(3) 0.046(2) -0.008(2) 0.0029(18) 0.010(2)
S1 0.0572(11) 0.0936(14) 0.0457(10) -0.0204(9) 0.0013(7) -0.0024(8)
C1 0.037(3) 0.045(3) 0.046(3) 0.003(2) 0.008(2) 0.001(2)
C2 0.039(3) 0.042(3) 0.045(3) 0.002(2) 0.012(2) -0.002(2)
C3 0.048(3) 0.057(4) 0.049(3) -0.003(3) 0.013(3) 0.003(3)
C4 0.054(4) 0.062(4) 0.062(4) -0.016(3) 0.021(3) -0.002(3)
C5 0.048(3) 0.073(4) 0.056(4) -0.018(3) 0.011(3) -0.013(3)
C6 0.050(3) 0.068(4) 0.048(3) -0.004(3) 0.004(3) -0.002(3)
C7 0.061(4) 0.064(4) 0.044(3) -0.010(3) 0.003(3) -0.001(3)
C8 0.040(3) 0.040(3) 0.041(3) 0.002(2) 0.005(2) 0.001(2)
C9 0.041(3) 0.038(3) 0.046(3) 0.001(2) 0.006(2) 0.001(2)
C10 0.060(4) 0.063(4) 0.057(4) -0.018(3) 0.012(3) 0.002(3)
C11 0.054(4) 0.062(4) 0.081(5) -0.019(3) 0.014(3) -0.010(4)
C12 0.043(3) 0.066(4) 0.062(4) -0.007(3) -0.001(3) -0.015(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
C1 N1 N2 119.5(4) n
C1 N1 H1 120.2 ?
N2 N1 H1 120.2 ?
C8 N2 N1 118.6(4) n
C6 N3 C2 116.7(5) ?
C12 S1 C9 92.0(3) ?
O1 C1 N1 123.9(5) n
O1 C1 C2 122.6(5) n
N1 C1 C2 113.6(5) n
N3 C2 C3 123.3(5) ?
N3 C2 C1 116.9(5) ?
C3 C2 C1 119.8(5) ?
C2 C3 C4 118.3(6) ?
C2 C3 H3 120.8 ?
C4 C3 H3 120.8 ?
C5 C4 C3 118.8(6) ?
C5 C4 H4 120.6 ?
C3 C4 H4 120.6 ?
C4 C5 C6 119.0(6) ?
C4 C5 H5 120.5 ?
C6 C5 H5 120.5 ?
N3 C6 C5 123.9(6) ?
N3 C6 H6 118.1 ?
C5 C6 H6 118.1 ?
C8 C7 H7A 109.5 ?
C8 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C8 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
N2 C8 C9 115.3(5) n
N2 C8 C7 127.4(5) ?
C9 C8 C7 117.4(5) ?
C10 C9 C8 128.9(5) ?
C10 C9 S1 110.4(4) ?
C8 C9 S1 120.7(4) ?
C9 C10 C11 112.9(6) ?
C9 C10 H10 123.5 ?
C11 C10 H10 123.5 ?
C12 C11 C10 112.8(6) ?
C12 C11 H11 123.6 ?
C10 C11 H11 123.6 ?
C11 C12 S1 111.9(5) ?
C11 C12 H12 124.1 ?
S1 C12 H12 124.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 1.335(7) n
N1 N2 1.384(6) n
N1 H1 0.8600 ?
N2 C8 1.285(7) n
N3 C6 1.331(7) ?
N3 C2 1.339(7) ?
O1 C1 1.215(6) n
S1 C12 1.709(6) n
S1 C9 1.716(6) n
C1 C2 1.497(7) ?
C2 C3 1.382(8) ?
C3 C4 1.384(8) ?
C3 H3 0.9300 ?
C4 C5 1.367(9) ?
C4 H4 0.9300 ?
C5 C6 1.370(9) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 C8 1.512(7) ?
C7 H7A 0.9600 ?
C7 H7B 0.9600 ?
C7 H7C 0.9600 ?
C8 C9 1.460(7) ?
C9 C10 1.359(8) ?
C10 C11 1.419(9) ?
C10 H10 0.9300 ?
C11 C12 1.330(9) ?
C11 H11 0.9300 ?
C12 H12 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C7 H7A O1 4_575 0.96 2.50 3.250(7) 134.5
N1 H1 O1 4_575 0.86 2.69 3.337(6) 133.1
C11 H11 N2 2_655 0.93 2.60 3.306(8) 133.2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4687550
