#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006326.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_2006326
loop_
_publ_author_name
'Rymarczyk, B. M.'
'Preut, H.'
'Kreher, R. P.'
_publ_contact_author
;       Dr. Hans Preut
    Fachbereich Chemie
    Universit\"at Dortmund
    Otto-Hahn-Str. 6
    44221 Dortmund
    Germany
;
_publ_section_title
;
 An Eight-Membered N,N,S,S-Heterocyclic Compound:
 4,7-Bis(4-chlorophenyl)-3,8-dihydro-1,2,5,6-dithiadiazocine
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              931
_journal_page_last               933
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C16 H12 Cl2 N2 S2'
_chemical_formula_weight         367.30
_chemical_name_systematic
;
 4,7-Bis[4'-chlorophenyl]-3,8-dihydro-1,2,5,6-dithiadiazocine
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 115.56(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.826(2)
_cell_length_b                   17.899(4)
_cell_length_c                   10.307(2)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    291.0(10)
_cell_measurement_theta_max      13.3
_cell_measurement_theta_min      7.3
_cell_volume                     1635.3(7)
_computing_cell_refinement       'R3m/V software'
_computing_data_collection       'R3m/V software'
_computing_data_reduction        'R3m/V software'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  'SHELXL93, PARST95 (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291.0(10)
_diffrn_measurement_device       'Siemens R3m/V'
_diffrn_measurement_method       \w--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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3630
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        '< 6'
_diffrn_standards_interval_count 300
_diffrn_standards_interval_time  300
_diffrn_standards_number         6
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      'not determined'
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.403
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.988
_refine_ls_goodness_of_fit_obs   1.166
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_restrained_S_obs      1.166
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_obs          0.0629
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.1116P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1770
_refine_ls_wR_factor_obs         0.1637
_reflns_number_observed          1840
_reflns_number_total             2867
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    na1282.cif
_[local]_cod_data_source_block   nic494
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_original_cell_volume        1635.3(6)
_cod_database_code               2006326
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_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 0.0645(8) 0.0676(8) 0.0462(6) 0.0018(6) 0.0276(6) 0.0062(6)
S2 0.0660(8) 0.0579(7) 0.0440(6) 0.0042(6) 0.0247(5) 0.0084(5)
Cl2 0.0440(7) 0.0997(10) 0.0554(7) -0.0008(6) 0.0160(5) -0.0121(6)
Cl1 0.0446(7) 0.0684(9) 0.0972(10) -0.0036(6) 0.0136(7) 0.0184(7)
N1 0.043(2) 0.062(2) 0.050(2) 0.004(2) 0.012(2) 0.016(2)
N2 0.045(2) 0.054(2) 0.052(2) 0.002(2) 0.013(2) 0.014(2)
C1 0.050(2) 0.044(2) 0.042(2) 0.001(2) 0.016(2) 0.000(2)
C2 0.058(3) 0.059(3) 0.041(2) 0.005(3) 0.014(2) -0.007(2)
C3 0.049(2) 0.049(3) 0.043(2) 0.000(2) 0.020(2) 0.005(2)
C4 0.049(3) 0.057(3) 0.038(2) -0.005(2) 0.018(2) -0.007(2)
C11 0.043(3) 0.045(2) 0.069(3) 0.006(2) 0.016(2) 0.010(2)
C12 0.054(3) 0.065(3) 0.074(3) 0.006(2) 0.033(3) 0.002(3)
C13 0.063(3) 0.074(3) 0.051(3) 0.007(3) 0.030(2) -0.003(2)
C14 0.047(2) 0.046(2) 0.049(2) 0.006(2) 0.021(2) 0.003(2)
C15 0.046(3) 0.077(3) 0.046(2) 0.001(2) 0.020(2) 0.005(2)
C16 0.056(3) 0.080(4) 0.052(3) 0.005(3) 0.022(2) 0.016(2)
C21 0.046(2) 0.070(3) 0.039(2) 0.005(2) 0.018(2) -0.002(2)
C22 0.056(3) 0.054(3) 0.080(4) 0.015(3) 0.012(3) 0.011(3)
C23 0.055(3) 0.046(3) 0.082(4) -0.002(2) 0.014(3) 0.005(3)
C24 0.052(2) 0.046(2) 0.046(2) 0.000(2) 0.024(2) 0.005(2)
C25 0.058(3) 0.045(3) 0.049(2) 0.002(2) 0.022(2) 0.004(2)
C26 0.053(3) 0.051(3) 0.050(2) -0.008(2) 0.019(2) -0.006(2)
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 0.61383(14) 0.29306(7) 0.17246(12) 0.0581(4) Uani d 1 S
S2 0.82362(14) 0.25332(7) 0.22183(12) 0.0557(4) Uani d 1 S
Cl2 1.56782(13) 0.40019(8) 0.46188(13) 0.0683(4) Uani d 1 Cl
Cl1 -0.06221(14) 0.41930(8) -0.4441(2) 0.0761(5) Uani d 1 Cl
N1 0.6841(4) 0.4046(2) -0.0738(4) 0.0540(9) Uani d 1 N
N2 0.8370(4) 0.4092(2) 0.0159(4) 0.0529(9) Uani d 1 N
C1 0.5873(5) 0.4015(2) -0.0209(4) 0.0466(10) Uani d 1 C
C2 0.6299(6) 0.3924(3) 0.1375(5) 0.0553(12) Uani d 1 C
H2A 0.726(4) 0.4070(19) 0.190(4) 0.026(9) Uiso d 1 H
H2B 0.560(5) 0.418(2) 0.163(4) 0.042(11) Uiso d 1 H
C3 0.9141(5) 0.3502(2) 0.0715(4) 0.0471(10) Uani d 1 C
C4 0.8471(6) 0.2740(3) 0.0588(5) 0.0480(10) Uani d 1 C
H4A 0.753(5) 0.277(2) -0.022(5) 0.043(11) Uiso d 1 H
H4B 0.917(4) 0.241(2) 0.057(4) 0.026(9) Uiso d 1 H
C11 0.1257(5) 0.4118(2) -0.3209(5) 0.0553(12) Uani d 1 C
C12 0.1623(6) 0.4111(3) -0.1771(6) 0.0628(13) Uani d 1 C
H12 0.082(10) 0.397(4) -0.145(9) 0.15(3) Uiso d 1 H
C13 0.3120(6) 0.4055(3) -0.0795(5) 0.0609(13) Uani d 1 C
H13 0.348(5) 0.407(2) 0.023(5) 0.049(12) Uiso d 1 H
C14 0.4269(5) 0.4037(2) -0.1238(4) 0.0471(10) Uani d 1 C
C15 0.3850(5) 0.4036(3) -0.2698(5) 0.0563(12) Uani d 1 C
H15 0.451(6) 0.397(3) -0.308(6) 0.081(18) Uiso d 1 H
C16 0.2373(6) 0.4076(3) -0.3682(6) 0.0631(13) Uani d 1 C
H16 0.201(6) 0.417(3) -0.474(6) 0.086(17) Uiso d 1 H
C21 1.3810(5) 0.3850(3) 0.3452(4) 0.0516(11) Uani d 1 C
C22 1.3227(6) 0.3147(3) 0.3244(6) 0.0696(15) Uani d 1 C
H22 1.373(6) 0.272(3) 0.358(6) 0.072(16) Uiso d 1 H
C23 1.1734(6) 0.3027(3) 0.2343(6) 0.0664(14) Uani d 1 C
H23 1.115(6) 0.265(3) 0.229(5) 0.067(16) Uiso d 1 H
C24 1.0762(5) 0.3618(2) 0.1625(4) 0.0470(10) Uani d 1 C
C25 1.1404(5) 0.4317(3) 0.1836(5) 0.0510(11) Uani d 1 C
H25 1.093(5) 0.475(3) 0.143(5) 0.055(13) Uiso d 1 H
C26 1.2910(5) 0.4442(3) 0.2732(5) 0.0525(11) Uani d 1 C
H26 1.322(6) 0.494(4) 0.277(6) 0.089(18) Uiso d 1 H
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C2 S1 S2 103.0(2) y
C4 S2 S1 102.5(2) y
C1 N1 N2 120.5(4) y
C3 N2 N1 120.8(4) y
N1 C1 C14 116.8(4) ?
N1 C1 C2 123.6(4) y
C14 C1 C2 119.5(4) ?
C1 C2 S1 108.0(3) y
C1 C2 H2A 110.(2) ?
S1 C2 H2A 109.(2) ?
C1 C2 H2B 111.(3) ?
S1 C2 H2B 106.(2) ?
H2A C2 H2B 113.(3) ?
N2 C3 C24 115.9(4) ?
N2 C3 C4 124.0(4) y
C24 C3 C4 119.9(4) ?
C3 C4 S2 109.2(3) y
C3 C4 H4A 105.(3) ?
S2 C4 H4A 111.(2) ?
C3 C4 H4B 106.(2) ?
S2 C4 H4B 107.(2) ?
H4A C4 H4B 119.(3) ?
C12 C11 C16 120.3(4) ?
C12 C11 Cl1 119.5(4) ?
C16 C11 Cl1 120.1(4) ?
C11 C12 C13 119.3(5) ?
C11 C12 H12 119.(5) ?
C13 C12 H12 119.(5) ?
C12 C13 C14 121.6(5) ?
C12 C13 H13 125.(3) ?
C14 C13 H13 113.(3) ?
C15 C14 C13 117.2(4) ?
C15 C14 C1 120.6(4) ?
C13 C14 C1 122.2(4) ?
C16 C15 C14 122.1(5) ?
C16 C15 H15 115.(4) ?
C14 C15 H15 123.(4) ?
C15 C16 C11 119.4(5) ?
C15 C16 H16 126.(3) ?
C11 C16 H16 114.(3) ?
C22 C21 C26 119.9(4) ?
C22 C21 Cl2 120.2(4) ?
C26 C21 Cl2 119.8(4) ?
C21 C22 C23 120.4(5) ?
C21 C22 H22 127.(3) ?
C23 C22 H22 112.(3) ?
C22 C23 C24 121.6(5) ?
C22 C23 H23 130.(4) ?
C24 C23 H23 106.(3) ?
C25 C24 C23 116.2(4) ?
C25 C24 C3 121.7(4) ?
C23 C24 C3 122.2(4) ?
C24 C25 C26 122.6(5) ?
C24 C25 H25 126.(3) ?
C26 C25 H25 111.(3) ?
C21 C26 C25 119.3(5) ?
C21 C26 H26 126.(4) ?
C25 C26 H26 115.(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 1.835(5) y
S1 S2 2.027(2) y
S2 C4 1.829(4) y
Cl2 C21 1.728(4) ?
Cl1 C11 1.737(5) ?
N1 C1 1.286(6) y
N1 N2 1.386(5) y
N2 C3 1.281(5) y
C1 C14 1.472(6) ?
C1 C2 1.510(6) y
C2 H2A 0.90(4) ?
C2 H2B 0.95(4) ?
C3 C24 1.473(6) ?
C3 C4 1.496(6) y
C4 H4A 0.94(4) ?
C4 H4B 0.91(4) ?
C11 C12 1.366(7) ?
C11 C16 1.381(7) ?
C12 C13 1.382(7) ?
C12 H12 1.01(9) ?
C13 C14 1.388(6) ?
C13 H13 0.96(5) ?
C14 C15 1.379(6) ?
C15 C16 1.368(7) ?
C15 H15 0.90(6) ?
C16 H16 1.01(5) ?
C21 C22 1.360(7) ?
C21 C26 1.374(7) ?
C22 C23 1.374(8) ?
C22 H22 0.89(5) ?
C23 C24 1.403(6) ?
C23 H23 0.87(5) ?
C24 C25 1.375(6) ?
C25 C26 1.383(6) ?
C25 H25 0.91(5) ?
C26 H26 0.93(6) ?
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
_geom_torsion_publ_flag
C2 S1 S2 C4 -59.7(2) y
C1 N1 N2 C3 83.6(5) y
N2 N1 C1 C14 174.6(4) ?
N2 N1 C1 C2 -8.3(6) y
N1 C1 C2 S1 -96.9(5) y
C14 C1 C2 S1 80.1(4) ?
S2 S1 C2 C1 91.0(3) y
N1 N2 C3 C24 178.7(4) ?
N1 N2 C3 C4 -6.5(6) y
N2 C3 C4 S2 -98.0(5) y
C24 C3 C4 S2 76.6(4) ?
S1 S2 C4 C3 89.5(3) y
C16 C11 C12 C13 -0.5(7) ?
Cl1 C11 C12 C13 -179.7(4) ?
C11 C12 C13 C14 2.7(8) ?
C12 C13 C14 C15 -3.5(7) ?
C12 C13 C14 C1 176.8(4) ?
N1 C1 C14 C15 4.5(6) ?
C2 C1 C14 C15 -172.8(4) ?
N1 C1 C14 C13 -175.8(4) ?
C2 C1 C14 C13 6.9(6) ?
C13 C14 C15 C16 2.1(7) ?
C1 C14 C15 C16 -178.2(5) ?
C14 C15 C16 C11 -0.1(8) ?
C12 C11 C16 C15 -0.8(8) ?
Cl1 C11 C16 C15 178.4(4) ?
C26 C21 C22 C23 -1.6(8) ?
Cl2 C21 C22 C23 178.5(4) ?
C21 C22 C23 C24 -0.7(9) ?
C22 C23 C24 C25 2.2(8) ?
C22 C23 C24 C3 -176.7(5) ?
N2 C3 C24 C25 -1.1(6) ?
C4 C3 C24 C25 -176.2(4) ?
N2 C3 C24 C23 177.8(4) ?
C4 C3 C24 C23 2.7(6) ?
C23 C24 C25 C26 -1.7(7) ?
C3 C24 C25 C26 177.3(4) ?
C22 C21 C26 C25 2.1(7) ?
Cl2 C21 C26 C25 -178.0(3) ?
C24 C25 C26 C21 -0.4(7) ?