#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007136.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_2007136
loop_
_publ_author_name
'Elerman, Y.'
'Elmali, A.'
_publ_section_title
;
 2-Salicylideneamino-4,5,6,7-tetrahydrobenzo[<i>b</i>]thiophene-3-carbonitrile
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              529
_journal_page_last               531
_journal_volume                  54
_journal_year                    1998
_chemical_formula_sum            'C16 H14 N2 O S'
_chemical_formula_weight         282.35
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.424(4)
_cell_length_b                   14.303(3)
_cell_length_c                   26.510(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.54
_cell_measurement_theta_min      2.75
_cell_volume                     2815.0(16)
_computing_cell_refinement       SDP
_computing_data_collection       'SDP (Frenz, 1985)'
_computing_data_reduction        SDP
_computing_molecular_graphics
'ORTEPII (Johnson, 1976); PLUTON (Spek, 1991)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2156
_diffrn_reflns_theta_max         25.63
_diffrn_reflns_theta_min         1.54
_diffrn_standards_decay_%        5.2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.508
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.083
_refine_ls_goodness_of_fit_obs   1.238
_refine_ls_hydrogen_treatment    'H atoms: riding with fixed U's '
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         1809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_restrained_S_obs      1.238
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_obs          0.0338
_refine_ls_shift/esd_max         0.003
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+0.1935P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.0902
_refine_ls_wR_factor_obs         0.0876
_reflns_number_observed          1353
_reflns_number_total             1809
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ab1510.cif
_[local]_cod_data_source_block   zer2
_cod_database_code               2007136
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.0539(3) 0.0452(3) 0.0427(3) 0.0004(2) -0.0001(2) -0.0037(2)
O1 0.0802(9) 0.0688(8) 0.0496(7) -0.0105(6) 0.0020(6) -0.0103(6)
N1 0.0397(7) 0.0514(8) 0.0378(7) 0.0053(6) 0.0035(6) 0.0009(6)
N2 0.0741(11) 0.0665(12) 0.1079(14) 0.0025(8) -0.0118(9) -0.0251(10)
C1 0.0387(8) 0.0617(10) 0.0452(9) 0.0076(7) 0.0019(7) 0.0021(8)
C2 0.0689(11) 0.0847(14) 0.0408(9) 0.0134(10) -0.0062(8) -0.0071(9)
C3 0.0774(12) 0.098(2) 0.0431(10) 0.0220(11) -0.0017(9) 0.0099(11)
C4 0.0858(13) 0.0725(12) 0.0587(11) 0.0125(10) 0.0103(10) 0.0217(10)
C5 0.0680(11) 0.0605(10) 0.0554(10) 0.0080(9) 0.0053(8) 0.0097(8)
C6 0.0379(8) 0.0539(9) 0.0441(9) 0.0102(6) 0.0026(6) 0.0028(7)
C7 0.0551(10) 0.0546(11) 0.0427(9) 0.0057(7) -0.0014(7) -0.0031(7)
C8 0.0386(7) 0.0422(8) 0.0366(8) 0.0072(6) -0.0009(6) -0.0016(6)
C9 0.0390(8) 0.0456(8) 0.0450(8) 0.0087(6) 0.0033(6) -0.0051(7)
C10 0.0436(8) 0.0517(9) 0.0433(8) 0.0056(7) 0.0027(6) 0.0043(7)
C11 0.0435(8) 0.0497(9) 0.0415(8) 0.0103(7) 0.0033(7) -0.0021(7)
C12 0.0530(10) 0.0800(12) 0.0393(9) 0.0100(8) 0.0015(7) -0.0067(8)
C13 0.112(2) 0.093(2) 0.0421(11) 0.0017(13) -0.0027(11) 0.0040(9)
C14 0.107(2) 0.091(2) 0.0570(11) -0.0047(13) 0.0058(11) 0.0221(11)
C15 0.0725(12) 0.0625(11) 0.0585(11) -0.0082(9) 0.0036(9) 0.0157(8)
C16 0.0548(9) 0.0478(9) 0.0560(9) 0.0062(8) -0.0032(8) -0.0087(8)
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
_atom_site_occupancy
_atom_site_type_symbol
S1 0.23966(5) 0.17660(3) 0.309286(14) 0.0472(2) Uani d 1 S
O1 0.1410(2) 0.04699(9) 0.11946(5) 0.0662(4) Uani d 1 O
H1O 0.136(3) 0.0494(15) 0.1525(10) 0.079 Uiso d 1 H
N1 0.1919(2) 0.10887(9) 0.21165(5) 0.0430(3) Uani d 1 N
N2 0.0156(2) -0.12647(13) 0.23505(8) 0.0829(6) Uani d 1 N
C1 0.2006(2) 0.13229(12) 0.10410(6) 0.0486(4) Uani d 1 C
C2 0.2051(3) 0.1503(2) 0.05301(6) 0.0648(5) Uani d 1 C
H2 0.1694 0.1045 0.0302 0.078 Uiso calc 1 H
C3 0.2622(3) 0.2359(2) 0.03566(7) 0.0727(6) Uani d 1 C
H3 0.2621 0.2480 0.0012 0.087 Uiso calc 1 H
C4 0.3192(3) 0.30349(15) 0.06855(8) 0.0723(6) Uani d 1 C
H4 0.3616 0.3604 0.0564 0.087 Uiso calc 1 H
C5 0.3133(3) 0.28674(13) 0.11947(7) 0.0613(5) Uani d 1 C
H5 0.3496 0.3333 0.1418 0.074 Uiso calc 1 H
C6 0.2535(2) 0.20071(12) 0.13850(6) 0.0453(4) Uani d 1 C
C7 0.2462(2) 0.18624(13) 0.19265(6) 0.0508(5) Uani d 1 C
H7 0.2819 0.2343 0.2141 0.061 Uiso calc 1 H
C8 0.1867(2) 0.09543(10) 0.26342(5) 0.0392(3) Uani d 1 C
C9 0.1356(2) 0.01267(10) 0.28513(6) 0.0432(4) Uani d 1 C
C10 0.1446(2) 0.01298(11) 0.33919(6) 0.0462(4) Uani d 1 C
C11 0.1977(2) 0.09704(11) 0.35694(6) 0.0449(4) Uani d 1 C
C12 0.2169(2) 0.12096(15) 0.41176(6) 0.0575(5) Uani d 1 C
H12A 0.3266 0.1566 0.4169 0.069 Uiso calc 1 H
H12B 0.1159 0.1592 0.4224 0.069 Uiso calc 1 H
C13 0.2231(4) 0.0342(2) 0.44248(7) 0.0824(7) Uani d 1 C
H13A 0.3429 0.0076 0.4401 0.099 Uiso calc 1 H
H13B 0.2022 0.0504 0.4775 0.099 Uiso calc 1 H
C14 0.0903(4) -0.0376(2) 0.42724(8) 0.0849(7) Uani d 1 C
H14A -0.0300 -0.0129 0.4324 0.102 Uiso calc 1 H
H14B 0.1039 -0.0917 0.4490 0.102 Uiso calc 1 H
C15 0.1082(3) -0.06890(13) 0.37268(7) 0.0645(5) Uani d 1 C
H15A 0.2059 -0.1136 0.3698 0.077 Uiso calc 1 H
H15B -0.0021 -0.0995 0.3621 0.077 Uiso calc 1 H
C16 0.0716(3) -0.06489(12) 0.25680(6) 0.0529(4) Uani d 1 C
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'
O O 0.0106 0.0060 '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'
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
C8 S1 C11 91.77(8) yes
C1 O1 H1O 106.1(15) ?
C7 N1 C8 121.18(13) yes
O1 C1 C2 118.0(2) yes
O1 C1 C6 121.70(15) yes
C2 C1 C6 120.3(2) ?
C3 C2 C1 120.2(2) ?
C3 C2 H2 119.9(2) ?
C1 C2 H2 119.9(2) ?
C4 C3 C2 120.7(2) ?
C4 C3 H3 119.6(2) ?
C2 C3 H3 119.6(2) ?
C3 C4 C5 119.6(2) ?
C3 C4 H4 120.2(2) ?
C5 C4 H4 120.2(2) ?
C4 C5 C6 121.2(2) ?
C4 C5 H5 119.4(2) ?
C6 C5 H5 119.4(2) ?
C1 C6 C5 118.0(2) ?
C1 C6 C7 122.4(2) ?
C5 C6 C7 119.5(2) ?
N1 C7 C6 121.6(2) yes
N1 C7 H7 119.2(2) ?
C6 C7 H7 119.2(2) ?
C9 C8 N1 122.92(13) yes
C9 C8 S1 110.38(10) yes
N1 C8 S1 126.70(11) yes
C8 C9 C16 123.03(14) ?
C8 C9 C10 113.83(13) ?
C16 C9 C10 123.08(14) ?
C11 C10 C9 111.39(13) ?
C11 C10 C15 122.93(14) ?
C9 C10 C15 125.64(14) ?
C10 C11 C12 124.7(2) ?
C10 C11 S1 112.59(12) yes
C12 C11 S1 122.74(13) yes
C13 C12 C11 110.1(2) ?
C13 C12 H12A 109.6(2) ?
C11 C12 H12A 109.64(15) ?
C13 C12 H12B 109.6(2) ?
C11 C12 H12B 109.64(15) ?
H12A C12 H12B 108.2(2) ?
C14 C13 C12 114.2(2) ?
C14 C13 H13A 108.7(2) ?
C12 C13 H13A 108.7(2) ?
C14 C13 H13B 108.7(2) ?
C12 C13 H13B 108.7(2) ?
H13A C13 H13B 107.6(2) ?
C13 C14 C15 113.9(2) ?
C13 C14 H14A 108.8(2) ?
C15 C14 H14A 108.8(2) ?
C13 C14 H14B 108.8(2) ?
C15 C14 H14B 108.8(2) ?
H14A C14 H14B 107.7(2) ?
C10 C15 C14 110.5(2) ?
C10 C15 H15A 109.5(2) ?
C14 C15 H15A 109.5(2) ?
C10 C15 H15B 109.5(2) ?
C14 C15 H15B 109.5(2) ?
H15A C15 H15B 108.1(2) ?
N2 C16 C9 177.8(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 1.7265(14) yes
S1 C11 1.729(2) yes
O1 C1 1.360(2) yes
O1 H1O 0.88(2) ?
N1 C7 1.281(2) yes
N1 C8 1.386(2) yes
N2 C16 1.132(2) yes
C1 C2 1.379(2) ?
C1 C6 1.394(2) ?
C2 C3 1.374(3) ?
C2 H2 0.930(2) ?
C3 C4 1.369(3) ?
C3 H3 0.930(2) ?
C4 C5 1.372(3) ?
C4 H4 0.930(2) ?
C5 C6 1.402(3) ?
C5 H5 0.930(2) ?
C6 C7 1.452(2) ?
C7 H7 0.930(2) ?
C8 C9 1.370(2) ?
C9 C16 1.422(2) ?
C9 C10 1.435(2) ?
C10 C11 1.350(2) ?
C10 C15 1.494(2) ?
C11 C12 1.500(2) ?
C12 C13 1.485(3) ?
C12 H12A 0.970(2) ?
C12 H12B 0.970(2) ?
C13 C14 1.480(4) ?
C13 H13A 0.970(3) ?
C13 H13B 0.970(2) ?
C14 C15 1.520(3) ?
C14 H14A 0.970(3) ?
C14 H14B 0.970(2) ?
C15 H15A 0.970(2) ?
C15 H15B 0.970(2) ?
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
O1 C1 C2 C3 179.2(2)
C6 C1 C2 C3 0.1(3)
C1 C2 C3 C4 1.5(3)
C2 C3 C4 C5 -2.3(3)
C3 C4 C5 C6 1.4(3)
O1 C1 C6 C5 179.96(15)
C2 C1 C6 C5 -1.0(2)
O1 C1 C6 C7 -0.9(2)
C2 C1 C6 C7 178.2(2)
C4 C5 C6 C1 0.2(3)
C4 C5 C6 C7 -178.9(2)
C8 N1 C7 C6 179.51(13)
C1 C6 C7 N1 0.6(2)
C5 C6 C7 N1 179.78(15)
C7 N1 C8 C9 -177.63(14)
C7 N1 C8 S1 2.8(2)
C11 S1 C8 C9 1.42(12)
C11 S1 C8 N1 -178.98(13)
N1 C8 C9 C16 -4.4(2)
S1 C8 C9 C16 175.22(13)
N1 C8 C9 C10 178.35(13)
S1 C8 C9 C10 -2.0(2)
C8 C9 C10 C11 1.7(2)
C16 C9 C10 C11 -175.53(15)
C8 C9 C10 C15 -176.0(2)
C16 C9 C10 C15 6.8(2)
C9 C10 C11 C12 178.68(14)
C15 C10 C11 C12 -3.6(3)
C9 C10 C11 S1 -0.6(2)
C15 C10 C11 S1 177.16(13)
C8 S1 C11 C10 -0.47(13)
C8 S1 C11 C12 -179.75(13)
C10 C11 C12 C13 16.8(2)
S1 C11 C12 C13 -164.05(14)
C11 C12 C13 C14 -42.9(2)
C12 C13 C14 C15 58.2(3)
C11 C10 C15 C14 15.1(3)
C9 C10 C15 C14 -167.5(2)
C13 C14 C15 C10 -41.1(3)
C8 C9 C16 N2 -120.(5)
C10 C9 C16 N2 58.(5)