#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006275.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_2006275
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 H10 Cl1 N3 S1'
_chemical_formula_sum            'C14 H10 Cl N3 S'
_chemical_formula_weight         287.77
_chemical_name_systematic
;
2-(5-chlorothien-2-ylmethylidenehydrazino)quinoline
;
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_type_scat_source           International_Tables_for_Xray_Crystallography
_cell_angle_alpha                90.000(8)
_cell_angle_beta                 90.000(10)
_cell_angle_gamma                90.000(10)
_cell_formula_units_Z            4
_cell_length_a                   4.6689(8)
_cell_length_b                   11.6030(10)
_cell_length_c                   23.744(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      16
_cell_measurement_theta_min      11
_cell_volume                     1286.3(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  0.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1362
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        -1.4
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.49
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    none
_exptl_crystal_description       Plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.14
_refine_ls_abs_structure_details
;
See Experimental
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.38
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.041
_refine_ls_R_factor_obs          0.027
_refine_ls_shift/esd_max         0.088
_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         0.038
_reflns_number_observed          1181
_reflns_number_total             1362
_reflns_observed_criterion       >3.0\s(I)
_[local]_cod_data_source_file    bk1314.cif
_[local]_cod_data_source_block   4
_[local]_cod_cif_authors_sg_H-M  'P 21 21 21 '
_[local]_cod_chemical_formula_sum_orig 'C14 H10 Cl1 N3 S1'
_cod_database_code               2006275
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
Cl 0.0689(5) 0.0498(3) 0.0669(4) -0.0113(4) 0.0116(4) 0.0141(3)
S 0.0499(3) 0.0350(3) 0.0477(3) 0.0003(3) 0.0088(3) -0.0020(3)
N1 0.0330(10) 0.0390(10) 0.0381(9) -0.0010(10) 0.0010(10) 0.0033(9)
N2 0.0370(10) 0.0316(9) 0.0420(10) 0.0000(10) 0.0060(10) 0.0053(8)
N3 0.0310(10) 0.0300(8) 0.0377(9) -0.0023(9) -0.0025(9) 0.0027(8)
C1 0.0370(10) 0.0420(10) 0.0430(10) -0.0010(10) 0.0000(10) 0.0060(10)
C2 0.0440(10) 0.0490(10) 0.0420(10) 0.0040(10) 0.0080(10) 0.0000(10)
C3 0.0460(10) 0.0360(10) 0.0460(10) 0.0010(10) 0.0040(10) -0.0040(10)
C4 0.0320(10) 0.0360(10) 0.0390(10) 0.0030(10) -0.0020(10) 0.0020(10)
C5 0.0350(10) 0.0330(10) 0.0440(10) 0.0020(10) -0.0010(10) 0.0050(10)
C6 0.0310(10) 0.0320(10) 0.0350(10) 0.0010(10) -0.0070(10) 0.0020(10)
C7 0.0410(10) 0.0330(10) 0.0490(10) -0.0040(10) 0.0060(10) 0.0100(10)
C8 0.0470(10) 0.0300(10) 0.0570(10) -0.0010(10) 0.0040(10) 0.0040(10)
C9 0.0360(10) 0.0350(10) 0.0410(10) 0.0030(10) -0.0040(10) -0.0020(10)
C10 0.0510(10) 0.0400(10) 0.0540(10) 0.0050(10) -0.0010(10) -0.0090(10)
C11 0.048(2) 0.060(2) 0.0490(10) 0.0050(10) 0.0040(10) -0.0110(10)
C12 0.0450(10) 0.060(2) 0.0450(10) -0.0030(10) 0.0080(10) 0.0030(10)
C13 0.0390(10) 0.0400(10) 0.0450(10) -0.0020(10) 0.0030(10) 0.0020(10)
C14 0.0280(10) 0.0360(10) 0.0360(10) 0.0020(10) -0.0060(10) 0.0020(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
_atom_site_calc_flag
Cl -0.9043(2) -0.15314(6) 0.74016(3) 0.0618(2) Uani ?
S -0.5302(2) -0.04750(5) 0.65314(3) 0.0442(2) Uani ?
N1 -0.1458(5) 0.0833(2) 0.57763(8) 0.0367(5) Uani ?
N2 0.0356(5) 0.1315(2) 0.53941(8) 0.0371(5) Uani ?
N3 0.3733(4) 0.1075(2) 0.46997(8) 0.0328(4) Uani ?
C1 -0.7536(6) -0.0333(2) 0.71000(10) 0.0408(6) Uani ?
C2 -0.7877(6) 0.0766(2) 0.72660(10) 0.0450(7) Uani ?
C3 -0.6292(6) 0.1528(2) 0.69290(10) 0.0425(6) Uani ?
C4 -0.4773(6) 0.1003(2) 0.65150(10) 0.0360(6) Uani ?
C5 -0.2852(5) 0.1493(2) 0.61040(10) 0.0372(6) Uani ?
C6 0.1862(5) 0.0592(2) 0.50446(9) 0.0324(5) Uani ?
C7 0.1366(6) -0.0621(2) 0.50670(10) 0.0410(6) Uani ?
C8 0.2750(6) -0.1307(2) 0.47060(10) 0.0443(6) Uani ?
C9 0.4727(6) -0.0844(2) 0.43150(10) 0.0374(6) Uani ?
C10 0.6224(7) -0.1506(2) 0.39140(10) 0.0483(7) Uani ?
C11 0.8127(7) -0.1010(3) 0.35580(10) 0.0523(8) Uani ?
C12 0.8599(6) 0.0175(3) 0.35790(10) 0.0498(7) Uani ?
C13 0.7153(6) 0.0852(2) 0.39560(10) 0.0415(6) Uani ?
C14 0.5170(5) 0.0369(2) 0.43350(9) 0.0332(5) Uani ?
H2n 0.014(6) 0.206(2) 0.5340(10) 0.054(8) Uiso ?
H2 -0.9045 0.0997 0.7574 0.0540 Uiso calc
H3 -0.6285 0.2339 0.6985 0.0509 Uiso calc
H5 -0.2629 0.2305 0.6079 0.0447 Uiso calc
H7 0.0071 -0.0936 0.5334 0.0492 Uiso calc
H8 0.2402 -0.2113 0.4711 0.0532 Uiso calc
H10 0.5894 -0.2313 0.3893 0.0580 Uiso calc
H11 0.9140 -0.1471 0.3294 0.0628 Uiso calc
H12 0.9939 0.0517 0.3329 0.0597 Uiso calc
H13 0.7493 0.1659 0.3963 0.0498 Uiso calc
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 S C4 90.50(10) ?
N2 N1 C5 118.6(2) yes
N1 N2 C6 118.0(2) yes
N1 N2 H2n 116.0(10) yes
C6 N2 H2n 124.0(10) yes
C6 N3 C14 117.5(2) yes
Cl C1 S 120.0(2) ?
Cl C1 C2 126.7(2) ?
S C1 C2 113.3(2) ?
C1 C2 C3 111.5(3) ?
C2 C3 C4 113.9(3) ?
S C4 C3 110.8(2) ?
S C4 C5 119.5(2) ?
C3 C4 C5 129.7(2) ?
N1 C5 C4 119.7(2) yes
N2 C6 N3 117.0(2) yes
N2 C6 C7 119.8(2) yes
N3 C6 C7 123.2(2) yes
C6 C7 C8 119.1(3) ?
C7 C8 C9 120.7(2) ?
C8 C9 C10 124.0(3) ?
C8 C9 C14 116.6(3) ?
C10 C9 C14 119.3(3) ?
C9 C10 C11 121.0(3) ?
C10 C11 C12 120.0(3) ?
C11 C12 C13 120.8(3) ?
C12 C13 C14 120.9(3) ?
N3 C14 C9 122.8(2) ?
N3 C14 C13 119.2(2) ?
C9 C14 C13 117.9(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C1 1.716(3) ?
S C1 1.714(3) ?
S C4 1.733(3) ?
N1 N2 1.362(3) yes
N1 C5 1.271(3) yes
N2 C6 1.374(3) yes
N2 H2n 0.88(5) yes
N3 C6 1.322(3) yes
N3 C14 1.368(3) yes
C1 C2 1.344(4) ?
C2 C3 1.405(4) ?
C3 C4 1.356(4) ?
C4 C5 1.442(4) yes
C6 C7 1.427(4) yes
C7 C8 1.336(4) ?
C8 C9 1.414(4) ?
C9 C10 1.409(4) ?
C9 C14 1.423(4) ?
C10 C11 1.355(5) ?
C11 C12 1.393(5) ?
C12 C13 1.370(4) ?
C13 C14 1.407(4) ?