#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202133.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_2202133
loop_
_publ_author_name
'Kobayashi, Tomoshige'
'Moriwaki, Takashi'
'Shiro, Motoo'
_publ_section_title
;
4,5,9,10-Tetrahydro-4,9-methanodithieno[3,2-b:3',2'-f][1,5]diazocine
;
_journal_issue 6
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o745
_journal_page_last o746
_journal_volume 59
_journal_year 2003
_chemical_formula_iupac 'C11 H10 N2 S2'
_chemical_formula_moiety 'C11 H10 N2 S2'
_chemical_formula_sum 'C11 H10 N2 S2'
_chemical_formula_weight 234.33
_chemical_melting_point 444
_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'
_cell_angle_alpha 90
_cell_angle_beta 112.58(2)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 7.700(2)
_cell_length_b 19.601(5)
_cell_length_c 7.332(2)
_cell_measurement_reflns_used 10963
_cell_measurement_temperature 93.2
_cell_measurement_theta_max 30.0
_cell_measurement_theta_min 3.0
_cell_volume 1021.8(5)
_computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation & Rigaku, 1999)'
_computing_molecular_graphics 'ORTEPII (Johnson, 1976)'
_computing_publication_material TEXSAN
_computing_structure_refinement TEXSAN
_computing_structure_solution 'SIR97 (Altomare et al., 1999)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9937
_diffrn_measured_fraction_theta_max 0.9937
_diffrn_measurement_device_type 'Rigaku R-AXIS RAPID Imaging Plate'
_diffrn_measurement_method \w
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.7107
_diffrn_reflns_av_R_equivalents 0.034
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 26
_diffrn_reflns_limit_k_min -27
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_number 12265
_diffrn_reflns_theta_full 30.03
_diffrn_reflns_theta_max 30.03
_exptl_absorpt_coefficient_mu 0.484
_exptl_absorpt_correction_T_max 0.976
_exptl_absorpt_correction_T_min 0.879
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.523
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 488.00
_exptl_crystal_size_max 0.150
_exptl_crystal_size_mid 0.100
_exptl_crystal_size_min 0.050
_refine_diff_density_max 0.69
_refine_diff_density_min -0.27
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.021
_refine_ls_hydrogen_treatment noref
_refine_ls_number_parameters 136
_refine_ls_number_reflns 2969
_refine_ls_R_factor_gt 0.0432
_refine_ls_shift/su_max 0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.057P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_ref 0.1013
_reflns_number_gt 2255
_reflns_number_total 2979
_reflns_threshold_expression F^2^>2\s(F^2^)
_[local]_cod_data_source_file ob6238.cif
_[local]_cod_data_source_block 2
_[local]_cod_cif_authors_sg_H-M 'P 21/c'
_cod_database_code 2202133
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
x,1/2-y,1/2+z
loop_
_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_occupancy
_atom_site_type_symbol
S1 0.77185(7) 0.69813(3) 0.84722(8) 0.01800(10) Uani d 1.00 S
S6 0.26015(7) 0.46034(2) 0.45873(7) 0.01420(10) Uani d 1.00 S
N4 0.2836(2) 0.62489(8) 0.8129(2) 0.0131(3) Uani d 1.00 N
N9 0.2245(2) 0.66101(8) 0.4729(2) 0.0128(4) Uani d 1.00 N
C2 0.7892(3) 0.65890(10) 1.0647(3) 0.0180(4) Uani d 1.00 C
C3 0.6215(3) 0.63271(10) 1.0528(3) 0.0157(4) Uani d 1.00 C
C5 0.2550(3) 0.55097(9) 0.7655(3) 0.0131(4) Uani d 1.00 C
C7 0.2474(3) 0.49660(10) 0.2395(3) 0.0157(4) Uani d 1.00 C
C8 0.2354(3) 0.56620(10) 0.2430(3) 0.0145(4) Uani d 1.00 C
C10 0.4067(3) 0.69710(10) 0.5264(3) 0.0149(4) Uani d 1.00 C
C11 0.5355(3) 0.67843(10) 0.7346(3) 0.0139(4) Uani d 1.00 C
C12 0.4761(3) 0.64410(10) 0.8628(3) 0.0131(4) Uani d 1.00 C
C13 0.2490(3) 0.53886(9) 0.5597(3) 0.0115(4) Uani d 1.00 C
C14 0.2376(2) 0.59025(10) 0.4287(3) 0.0117(4) Uani d 1.00 C
C15 0.1636(3) 0.66537(10) 0.6405(3) 0.0142(4) Uani d 1.00 C
H2 0.9023 0.6560 1.1789 0.0216 Uiso calc 1.00 H
H3 0.6032 0.6096 1.1579 0.0189 Uiso calc 1.00 H
H5a 0.3558 0.5257 0.8580 0.0158 Uiso calc 1.00 H
H5b 0.1397 0.5366 0.7721 0.0158 Uiso calc 1.00 H
H7 0.2487 0.4713 0.1295 0.0188 Uiso calc 1.00 H
H8 0.2266 0.5951 0.1357 0.0174 Uiso calc 1.00 H
H10a 0.4639 0.6842 0.4375 0.0179 Uiso calc 1.00 H
H10b 0.3856 0.7450 0.5184 0.0179 Uiso calc 1.00 H
H15a 0.0381 0.6490 0.5986 0.0170 Uiso calc 1.00 H
H15b 0.1678 0.7118 0.6793 0.0170 Uiso calc 1.00 H
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 0.0145(2) 0.0187(2) 0.0187(2) -0.0030(2) 0.0042(2) -0.0010(2)
S6 0.0157(2) 0.0125(2) 0.0138(2) -0.0002(2) 0.0051(2) -0.0006(2)
N4 0.0144(7) 0.0132(7) 0.0112(7) 0.0011(6) 0.0044(6) -0.0001(6)
N9 0.0153(7) 0.0111(7) 0.0120(7) 0.0002(6) 0.0053(6) 0.0010(6)
C2 0.0170(9) 0.0171(9) 0.0160(9) 0.0033(7) 0.0021(7) -0.0007(7)
C3 0.0194(9) 0.0145(8) 0.0110(8) 0.0033(7) 0.0033(7) -0.0006(6)
C5 0.0158(8) 0.0129(8) 0.0114(8) 0.0001(6) 0.0060(7) 0.0025(6)
C7 0.0161(9) 0.0206(9) 0.0118(8) -0.0003(7) 0.0069(7) -0.0022(7)
C8 0.0139(8) 0.0191(9) 0.0103(8) 0.0002(7) 0.0047(7) 0.0000(7)
C10 0.0172(9) 0.0144(8) 0.0127(8) -0.0016(7) 0.0053(7) 0.0014(7)
C11 0.0138(8) 0.0131(8) 0.0138(8) -0.0006(6) 0.0040(7) -0.0006(7)
C12 0.0142(8) 0.0119(8) 0.0124(8) 0.0010(6) 0.0043(7) -0.0013(6)
C13 0.0123(8) 0.0114(7) 0.0105(7) 0.0002(6) 0.0039(6) -0.0002(6)
C14 0.0113(8) 0.0132(8) 0.0096(7) 0.0013(6) 0.0030(6) 0.0007(6)
C15 0.0139(8) 0.0149(8) 0.0127(8) 0.0024(7) 0.0039(7) 0.0002(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
S S 0.125 0.123
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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
C2 S1 C11 92.04(10) ?
C7 S6 C13 92.17(9) ?
C5 N4 C12 111.20(10) ?
C5 N4 C15 109.60(10) ?
C12 N4 C15 108.8(2) ?
C10 N9 C14 112.30(10) ?
C10 N9 C15 108.80(10) ?
C14 N9 C15 108.40(10) ?
S1 C2 C3 111.90(10) ?
S1 C2 H2 124.0 no
C3 C2 H2 124.0 no
C2 C3 C12 111.9(2) ?
C2 C3 H3 124.1 no
C12 C3 H3 124.1 no
N4 C5 C13 109.30(10) ?
N4 C5 H5a 109.5 no
N4 C5 H5b 109.5 no
C13 C5 H5a 109.5 no
C13 C5 H5b 109.5 no
H5a C5 H5b 109.5 no
S6 C7 C8 111.90(10) ?
S6 C7 H7 124.0 no
C8 C7 H7 124.1 no
C7 C8 C14 111.7(2) ?
C7 C8 H8 124.2 no
C14 C8 H8 124.2 no
N9 C10 C11 109.8(2) ?
N9 C10 H10a 109.4 no
N9 C10 H10b 109.4 no
C11 C10 H10a 109.4 no
C11 C10 H10b 109.4 no
H10a C10 H10b 109.5 no
S1 C11 C10 126.20(10) ?
S1 C11 C12 110.50(10) ?
C10 C11 C12 123.3(2) ?
N4 C12 C3 123.6(2) ?
N4 C12 C11 122.6(2) ?
C3 C12 C11 113.7(2) ?
S6 C13 C5 125.60(10) ?
S6 C13 C14 110.80(10) ?
C5 C13 C14 123.6(2) ?
N9 C14 C8 123.7(2) ?
N9 C14 C13 122.8(2) ?
C8 C14 C13 113.4(2) ?
N4 C15 N9 112.7(2) ?
N4 C15 H15a 108.7 no
N4 C15 H15b 108.7 no
N9 C15 H15a 108.7 no
N9 C15 H15b 108.7 no
H15a C15 H15b 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 1.728(2) yes
S1 C11 1.729(2) yes
S6 C7 1.726(2) yes
S6 C13 1.724(2) yes
N4 C5 1.486(2) yes
N4 C12 1.433(2) yes
N4 C15 1.478(2) yes
N9 C10 1.483(3) yes
N9 C14 1.437(2) yes
N9 C15 1.477(2) yes
C2 C3 1.362(3) yes
C2 H2 0.950 no
C3 C12 1.430(3) yes
C3 H3 0.950 no
C5 C13 1.511(3) yes
C5 H5a 0.950 no
C5 H5b 0.950 no
C7 C8 1.368(3) yes
C7 H7 0.950 no
C8 C14 1.434(3) yes
C8 H8 0.950 no
C10 C11 1.512(3) yes
C10 H10a 0.950 no
C10 H10b 0.950 no
C11 C12 1.370(3) yes
C13 C14 1.371(3) yes
C15 H15a 0.950 no
C15 H15b 0.950 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
S1 C2 3.517(2) 4_564
N4 C8 3.508(3) 1_556
N9 C2 3.534(3) 1_454
C5 C8 3.574(3) 1_556
C10 C12 3.450(3) 4_564