#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006272.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_2006272
loop_
_publ_author_name
'Mague, J. T.'
'Vang, S.'
'Berge, D. G.'
'Wacholtz, W. F.'
_publ_section_title
;
 Isomerism/Tautomerism in Hydrazones Derived from Thiophenaldehydes and
 2-Hydrazinoquinoline
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              973
_journal_page_last               979
_journal_volume                  53
_journal_year                    1997
_chemical_formula_structural     'C14 H11 N3 S1'
_chemical_formula_sum            'C14 H11 N3 S'
_chemical_formula_weight         253.32
_chemical_name_systematic
;
2-(2-thienylmethylidenehydrazino)quinoline
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source           International_Tables_for_Xray_Crystallography
_cell_angle_alpha                90.000(10)
_cell_angle_beta                 92.050(10)
_cell_angle_gamma                90.000(10)
_cell_formula_units_Z            4
_cell_length_a                   11.1880(10)
_cell_length_b                   4.7460(10)
_cell_length_c                   23.012(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      16
_cell_measurement_theta_min      11
_cell_volume                     1221.1(3)
_computing_cell_refinement       CAD4_software
_computing_data_collection       CAD4_software_(Enraf-Nonius,_1989)
_computing_data_reduction        PROCESS_MolEN_(Fair,_1990)
_computing_molecular_graphics    ORTEPII_(Johnson,_1976)
_computing_publication_material  CIF_VAX_MolEN
_computing_structure_refinement  LSFM_MolEN
_computing_structure_solution    Direct_methods_(SIR;_Burla_et_al.,_1989)
_diffrn_ambient_temperature      293
_diffrn_measurement_device       Enraf_Nonius_CAD4
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            2575
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.25
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.38
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    none
_exptl_crystal_description       Column
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.45
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         1428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.084
_refine_ls_R_factor_obs          0.039
_refine_ls_shift/esd_max         0.009
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0016 Fo^4^]'
_refine_ls_wR_factor_obs         0.048
_reflns_number_observed          1428
_reflns_number_total             2156
_reflns_observed_criterion       >2.0\s(I)
_[local]_cod_data_source_file    bk1314.cif
_[local]_cod_data_source_block   1
_[local]_cod_chemical_formula_sum_orig 'C14 H11 N3 S1'
_cod_database_code               2006272
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 0.0516(3) 0.0657(4) 0.0735(4) 0.0131(4) -0.0004(3) -0.0153(4)
N1 0.0470(10) 0.0360(10) 0.0450(10) 0.0032(9) 0.0034(8) -0.0030(10)
N2 0.0396(9) 0.0430(10) 0.0480(10) 0.0011(9) 0.0039(8) -0.0080(9)
N3 0.0380(9) 0.0330(10) 0.0418(9) 0.0005(8) 0.0039(8) 0.0013(9)
C1 0.079(2) 0.055(2) 0.062(2) 0.0150(10) 0.0160(10) -0.0060(10)
C2 0.091(2) 0.047(2) 0.0460(10) -0.0060(10) 0.0080(10) -0.0080(10)
C3 0.0580(10) 0.052(2) 0.0460(10) -0.0070(10) 0.0030(10) -0.0010(10)
C4 0.0480(10) 0.0350(10) 0.0410(10) 0.0020(10) 0.0020(10) 0.0030(10)
C5 0.0420(10) 0.0400(10) 0.0480(10) 0.0010(10) 0.0030(10) 0.0030(10)
C6 0.0390(10) 0.0310(10) 0.0430(10) -0.0011(9) 0.0056(9) 0.0050(10)
C7 0.0390(10) 0.0460(10) 0.0600(10) 0.0020(10) 0.0090(10) -0.0100(10)
C8 0.0330(10) 0.0490(10) 0.070(2) -0.0010(10) 0.0050(10) -0.0010(10)
C9 0.0420(10) 0.0360(10) 0.0510(10) -0.0060(10) 0.0030(10) 0.0030(10)
C10 0.0470(10) 0.052(2) 0.067(2) -0.0090(10) -0.0040(10) -0.0020(10)
C11 0.0640(10) 0.056(2) 0.0560(10) -0.0190(10) -0.0060(10) -0.0050(10)
C12 0.0680(10) 0.0460(10) 0.0520(10) -0.0060(10) 0.0120(10) -0.0080(10)
C13 0.0480(10) 0.0420(10) 0.0500(10) -0.0010(10) 0.0060(10) -0.0020(10)
C14 0.0400(10) 0.0330(10) 0.0420(10) -0.0040(10) 0.0062(9) 0.0050(10)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
S1 0.19804(6) 0.5593(2) 0.40592(3) 0.0637(2) Uani
N1 0.3287(2) 0.1791(4) 0.32683(8) 0.0426(5) Uani
N2 0.3778(2) -0.0015(4) 0.28851(8) 0.0436(5) Uani
N3 0.35070(10) -0.3334(4) 0.21666(8) 0.0375(5) Uani
C1 0.2163(3) 0.7879(6) 0.46250(10) 0.0653(8) Uani
C2 0.3310(3) 0.8220(6) 0.47850(10) 0.0614(8) Uani
C3 0.4080(2) 0.6613(6) 0.44490(10) 0.0516(7) Uani
C4 0.3494(2) 0.5051(5) 0.40350(10) 0.0414(6) Uani
C5 0.3988(2) 0.3141(5) 0.36180(10) 0.0436(6) Uani
C6 0.3018(2) -0.1438(5) 0.25046(9) 0.0376(6) Uani
C7 0.1781(2) -0.0805(6) 0.24850(10) 0.0481(6) Uani
C8 0.1065(2) -0.2060(6) 0.20840(10) 0.0509(7) Uani
C9 0.1533(2) -0.4077(5) 0.17000(10) 0.0428(6) Uani
C10 0.0832(2) -0.5454(6) 0.12690(10) 0.0553(7) Uani
C11 0.1333(2) -0.7416(6) 0.09190(10) 0.0587(8) Uani
C12 0.2543(2) -0.8059(6) 0.09900(10) 0.0549(7) Uani
C13 0.3247(2) -0.6730(5) 0.14010(10) 0.0464(6) Uani
C14 0.2766(2) -0.4671(5) 0.17661(9) 0.0383(6) Uani
H1 0.147(2) 0.852(6) 0.4790(10) 0.087(9) Uiso
H2n 0.452(2) 0.002(5) 0.2834(8) 0.057(7) Uiso
H2 0.351(2) 0.942(6) 0.5080(10) 0.078(8) Uiso
H3 0.485(2) 0.666(5) 0.4522(9) 0.068(8) Uiso
H5 0.488(2) 0.297(5) 0.3608(9) 0.052(6) Uiso
H7 0.152(2) 0.049(5) 0.2735(8) 0.047(6) Uiso
H8 0.027(2) -0.163(5) 0.2051(9) 0.061(7) Uiso
H10 0.001(2) -0.503(5) 0.1250(10) 0.065(7) Uiso
H11 0.086(2) -0.835(6) 0.0620(10) 0.071(8) Uiso
H12 0.286(2) -0.926(5) 0.0768(8) 0.053(6) Uiso
H13 0.404(2) -0.717(5) 0.1461(9) 0.061(7) Uiso
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 S1 C4 91.6(2) ?
N2 N1 C5 118.1(2) yes
N1 N2 C6 117.8(2) yes
N1 N2 H2n 120(2) yes
C6 N2 H2n 121(2) yes
C6 N3 C14 117.2(2) yes
S1 C1 C2 112.1(2) ?
S1 C1 H1 117(2) ?
C2 C1 H1 131(2) ?
C1 C2 C3 112.7(3) ?
C1 C2 H2 120(2) ?
C3 C2 H2 128(2) ?
C2 C3 C4 113.1(3) ?
C2 C3 H3 120(2) ?
C4 C3 H3 127(2) ?
S1 C4 C3 110.4(2) ?
S1 C4 C5 121.1(2) ?
C3 C4 C5 128.5(2) ?
N1 C5 C4 119.6(2) yes
N1 C5 H5 122.0(10) ?
C4 C5 H5 118.0(10) ?
N2 C6 N3 116.7(2) yes
N2 C6 C7 119.9(2) yes
N3 C6 C7 123.4(2) yes
C6 C7 C8 119.2(3) ?
C6 C7 H7 118(2) ?
C8 C7 H7 123(2) ?
C7 C8 C9 120.3(3) ?
C7 C8 H8 121(2) ?
C9 C8 H8 119(2) ?
C8 C9 C10 123.1(2) ?
C8 C9 C14 116.8(2) ?
C10 C9 C14 120.1(2) ?
C9 C10 C11 120.2(3) ?
C9 C10 H10 117(2) ?
C11 C10 H10 123(2) ?
C10 C11 C12 120.0(3) ?
C10 C11 H11 120(2) ?
C12 C11 H11 120(2) ?
C11 C12 C13 121.0(3) ?
C11 C12 H12 120(2) ?
C13 C12 H12 119(2) ?
C12 C13 C14 120.8(3) ?
C12 C13 H13 122(2) ?
C14 C13 H13 117(2) ?
N3 C14 C9 123.0(2) ?
N3 C14 C13 119.1(2) ?
C9 C14 C13 117.9(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.701(3) ?
S1 C4 1.716(2) ?
N1 N2 1.360(3) yes
N1 C5 1.275(3) yes
N2 C6 1.376(3) yes
N2 H2n 0.85(3) yes
N3 C6 1.321(3) yes
N3 C14 1.373(3) yes
C1 C2 1.333(4) ?
C1 H1 0.93(3) ?
C2 C3 1.403(4) ?
C2 H2 0.90(3) ?
C3 C4 1.357(4) ?
C3 H3 0.87(3) ?
C4 C5 1.445(3) yes
C5 H5 1.00(2) ?
C6 C7 1.416(3) yes
C7 C8 1.340(4) ?
C7 H7 0.90(3) ?
C8 C9 1.415(4) ?
C8 H8 0.91(3) ?
C9 C10 1.404(4) ?
C9 C14 1.412(3) ?
C10 C11 1.364(4) ?
C10 H10 0.94(3) ?
C11 C12 1.392(4) ?
C11 H11 0.96(3) ?
C12 C13 1.364(4) ?
C12 H12 0.85(3) ?
C13 C14 1.407(3) ?
C13 H13 0.92(3) ?