#------------------------------------------------------------------------------
#$Date: 2012-02-03 18:16:24 +0100 (Fri, 03 Feb 2012) $
#$Revision: 32112 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/33/2003388.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_2003388
loop_
_publ_author_name
'Pilati, T.'
_publ_section_title
;
 Five 3,3'-Bridged 2,2'-Dithiophenes
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              690
_journal_page_last               697
_journal_volume                  51
_journal_year                    1995
_chemical_compound_source
;
chemical synthesis (Sannicol\`o, 1994).
;
_chemical_formula_sum            'C10 H8 O S2'
_chemical_formula_weight         208.29
_chemical_name_systematic
;
4H,6H-dithieno[3,2-c;2',3'-e]oxepine,
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 113.49(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.030(2)
_cell_length_b                   9.009(2)
_cell_length_c                   16.306(5)
_cell_measurement_radiation      'Mo K\a'
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      17.0
_cell_measurement_theta_min      10.7
_cell_measurement_wavelength     0.70930
_cell_volume                     1890.2(8)
_computing_cell_refinement       SDP
_computing_data_collection       'SDP (Frenz, 1983)'
_computing_data_reduction        SDP
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'PARST (Nardelli, 1983)'
_computing_structure_refinement  SDP
_computing_structure_solution    'MULTAN (Main et al., 1982)'
_diffrn_ambient_temperature      295(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       '\q/2\q scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus Philips Mo tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3848
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  360
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.4940
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.4639
_exptl_crystal_description
;
Irregular and partially rounded prism
;
_exptl_crystal_F_000             864.0
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.021
_refine_diff_density_min         >-0.21
_refine_ls_extinction_coef       5.2(4)x10^-7^
_refine_ls_extinction_method     'Stout & Jensen (1968) '
_refine_ls_goodness_of_fit_obs   1.841
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full-matrix
_refine_ls_number_parameters     300
_refine_ls_number_reflns         2466
_refine_ls_R_factor_obs          0.032
_refine_ls_shift/esd_max         0.003
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme
'w = 2F~o~Lp/[\s^2^(I~o~) + (0.02I~o~)^2^]^1/2^'
_refine_ls_wR_factor_obs         0.036
_reflns_number_observed          2466
_reflns_number_total             3701
_reflns_observed_criterion       'I~o~ > 2\s(I~o~)'
_[local]_cod_data_source_file    na1119.cif
_[local]_cod_data_source_block   III
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_cell_measurement_temperature' value 'room temperature' was changed
to '295(2)' - the room/ambient temperature average [293;298] in
Kelvins(K) was taken.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_cell_measurement_temperature' value 'room temperature' was changed
to '295(2)' - the room/ambient temperature average [293;298] in
Kelvins(K) was taken.

'_diffrn_ambient_temperature' value 'room
temperature' was changed to '295(2)' - the room/ambient temperature
average [293;298] in Kelvins(K) was taken.

'_symmetry_cell_setting'
value 'Monoclinic' changed to 'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1890.22(82)
_cod_database_code               2003388
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_22
_atom_site_aniso_U_23
_atom_site_aniso_U_33
S1a 0.0549(3) 0.0046(3) 0.0321(2) 0.0619(3) 0.0047(3) 0.0727(2)
S7a 0.0870(3) -0.0159(3) 0.0364(2) 0.0551(3) 0.0028(3) 0.0726(3)
O12a 0.0593(7) 0.0099(7) 0.0258(5) 0.0674(9) -0.0012(6) 0.0538(7)
C2a 0.070(1) 0.014(1) 0.0344(8) 0.053(1) 0.009(1) 0.079(1)
C3a 0.073(1) -0.002(1) 0.0341(8) 0.047(1) 0.005(1) 0.067(1)
C4a 0.0501(8) -0.0008(9) 0.0198(6) 0.046(1) -0.0027(9) 0.0451(9)
C5a 0.0465(8) -0.0016(9) 0.0145(6) 0.045(1) -0.0043(9) 0.0374(8)
C6a 0.059(1) -0.0043(9) 0.0166(7) 0.045(1) -0.0027(9) 0.0382(8)
C8a 0.124(2) -0.006(1) 0.033(1) 0.046(1) 0.009(1) 0.075(1)
C9a 0.099(2) 0.017(1) 0.023(1) 0.052(1) 0.005(1) 0.069(1)
C10a 0.067(1) 0.006(1) 0.0144(8) 0.049(1) -0.0014(9) 0.0426(9)
C11a 0.060(1) 0.014(1) 0.0130(9) 0.066(1) -0.004(1) 0.060(1)
C13a 0.068(1) 0.002(1) 0.0408(8) 0.063(1) 0.009(1) 0.079(1)
S1b 0.0731(3) 0.0157(3) 0.0300(2) 0.0539(3) 0.0110(3) 0.0913(3)
S7b 0.0759(3) 0.0239(4) 0.0098(2) 0.0920(5) 0.0110(3) 0.0576(3)
O12b 0.0601(8) 0.0194(7) 0.0213(6) 0.0660(9) 0.0139(8) 0.0752(8)
C2b 0.076(1) -0.006(1) 0.037(1) 0.060(1) -0.016(1) 0.109(2)
C3b 0.062(1) -0.008(1) 0.021(1) 0.073(2) -0.009(1) 0.075(1)
C4b 0.0464(9) -0.0002(9) 0.0214(7) 0.059(1) 0.006(1) 0.059(1)
C5b 0.0475(8) 0.0067(9) 0.0279(6) 0.049(1) 0.0102(9) 0.0607(9)
C6b 0.0457(8) 0.0086(9) 0.0227(6) 0.061(1) 0.010(1) 0.0511(9)
C8b 0.063(1) 0.014(1) 0.015(1) 0.108(2) -0.019(1) 0.067(1)
C9b 0.060(1) 0.002(1) 0.0327(8) 0.072(1) -0.013(1) 0.078(1)
C10b 0.0513(8) 0.0037(9) 0.0293(6) 0.057(1) 0.001(1) 0.0561(9)
C11b 0.085(1) 0.005(1) 0.0323(9) 0.049(1) 0.006(1) 0.070(1)
C13b 0.064(1) 0.004(1) 0.005(1) 0.071(1) 0.010(1) 0.065(1)
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_attached_atom
_atom_site_type_symbol
S1a -0.24609(4) 0.35192(7) 0.13717(4) 0.0611(2) aniso . S
S7a -0.29924(5) 0.69592(7) 0.09094(4) 0.0701(2) aniso . S
O12a -0.5328(1) 0.4976(2) 0.19257(8) 0.0591(5) aniso . O
C2a -0.2682(2) 0.1859(3) 0.1767(2) 0.0659(7) aniso . C
C3a -0.3563(2) 0.1883(2) 0.1903(1) 0.0605(8) aniso . C
C4a -0.4092(1) 0.3264(2) 0.1693(1) 0.0467(6) aniso . C
C5a -0.3582(1) 0.4277(2) 0.1394(1) 0.0438(6) aniso . C
C6a -0.3850(1) 0.5808(2) 0.1126(1) 0.0484(7) aniso . C
C8a -0.3855(2) 0.8394(3) 0.0635(2) 0.0838(12) aniso . C
C9a -0.4735(2) 0.8023(3) 0.0722(2) 0.0765(11) aniso . C
C10a -0.4753(2) 0.6542(2) 0.0994(1) 0.0551(7) aniso . C
C11a -0.5646(2) 0.5855(3) 0.1138(1) 0.0652(9) aniso . C
C13a -0.5100(2) 0.3490(3) 0.1797(1) 0.0661(8) aniso . C
S1b 0.08620(5) 0.36056(7) -0.00522(4) 0.0737(2) aniso . S
S7b 0.00317(5) 0.11700(8) -0.16322(4) 0.0805(3) aniso . S
O12b 0.2730(1) -0.0809(2) 0.07309(9) 0.0689(6) aniso . O
C2b 0.1692(2) 0.4134(3) 0.0997(2) 0.0815(10) aniso . C
C3b 0.2308(2) 0.3020(3) 0.1442(2) 0.0717(9) aniso . C
C4b 0.2135(1) 0.1678(2) 0.0947(1) 0.0547(7) aniso . C
C5b 0.1364(1) 0.1817(2) 0.0112(1) 0.0505(7) aniso . C
C6b 0.0907(1) 0.0702(2) -0.0575(1) 0.0514(6) aniso . C
C8b -0.0186(2) -0.0642(3) -0.1944(2) 0.0825(11) aniso . C
C9b 0.0394(2) -0.1557(3) -0.1282(2) 0.0682(8) aniso . C
C10b 0.1024(1) -0.0803(2) -0.0494(1) 0.0523(7) aniso . C
C11b 0.1753(2) -0.1551(2) 0.0335(2) 0.0674(8) aniso . C
C13b 0.2743(2) 0.0302(3) 0.1345(2) 0.0731(10) aniso . C
H2a -0.2240(10) 0.1100(20) 0.1850(10) 0.0925(79) iso C2a H
H3a -0.3820(10) 0.1090(20) 0.2110(10) 0.0700(68) iso C3a H
H8a -0.3690(20) 0.9290(30) 0.0470(10) 0.1160(93) iso C8a H
H9a -0.5230(20) 0.8620(20) 0.0630(10) 0.0962(81) iso C9a H
H111a -0.6050(10) 0.5260(20) 0.0630(10) 0.0880(77) iso C11a H
H112a -0.6020(10) 0.6640(20) 0.1220(10) 0.0866(78) iso C11a H
H131a -0.5660(20) 0.3050(20) 0.1250(10) 0.1022(85) iso C13a H
H132a -0.5060(10) 0.2990(20) 0.2320(10) 0.0821(73) iso C13a H
H2b 0.1690(20) 0.5110(20) 0.1190(10) 0.1026(87) iso C2b H
H3b 0.2810(10) 0.3070(20) 0.2030(10) 0.0809(74) iso C3b H
H8b -0.0680(20) -0.0970(30) -0.2530(20) 0.135(11) iso C8b H
H9b 0.0380(10) -0.2630(20) -0.1340(10) 0.0800(71) iso C9b H
H111b 0.1920(10) -0.2530(20) 0.0220(10) 0.0803(73) iso C11b H
H112b 0.1440(20) -0.1620(30) 0.0780(20) 0.1150(95) iso C11b H
H131b 0.3390(10) 0.0540(20) 0.1670(10) 0.0926(78) iso C13b H
H132b 0.2500(20) -0.0160(30) 0.1780(10) 0.1076(91) iso C13b H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
S Sulphur
;International Tables for X-ray Crystallography (1974, Vol. IV,
Tables 2.2A, 2.3.1 and 2.2C)
;
0.110 0.124
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-7 1 5
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
C2a S1a C5a 92.00(10) yes
C6a S7a C8a 91.70(10) yes
C11a O12a C13a 113.70(10) yes
S1a C2a H2a 120.0(10) no
S1a C2a C3a 111.5(2) yes
C3a C2a H2a 128.0(10) no
C2a C3a H3a 125.0(10) no
C2a C3a C4a 113.7(2) yes
C4a C3a H3a 122.0(10) no
C3a C4a C13a 121.1(2) yes
C3a C4a C5a 112.0(2) yes
C5a C4a C13a 126.9(2) yes
S1a C5a C4a 110.80(10) yes
C4a C5a C6a 129.3(2) yes
S1a C5a C6a 119.90(10) yes
S7a C6a C5a 120.90(10) yes
C5a C6a C10a 128.3(2) yes
S7a C6a C10a 110.80(10) yes
S7a C8a H8a 121(2) no
S7a C8a C9a 111.8(2) yes
C9a C8a H8a 127(2) no
C8a C9a H9a 123.0(10) no
C8a C9a C10a 113.7(3) yes
C10a C9a H9a 123(2) no
C6a C10a C9a 112.1(3) yes
C9a C10a C11a 124.2(2) yes
C6a C10a C11a 123.8(2) yes
O12a C11a C10a 113.0(2) yes
C10a C11a H112a 105.0(10) no
C10a C11a H111a 110.0(10) no
O12a C11a H112a 107.0(10) no
O12a C11a H111a 109.0(10) no
H111a C11a H112a 112.0(10) no
O12a C13a C4a 115.1(2) yes
C4a C13a H132a 108.0(10) no
C4a C13a H131a 107.0(10) no
O12a C13a H132a 105.0(10) no
O12a C13a H131a 111.0(10) no
H131a C13a H132a 111.0(10) no
C2b S1b C5b 91.80(10) yes
C6b S7b C8b 92.00(10) yes
C11b O12b C13b 113.1(2) yes
S1b C2b H2b 120.0(10) no
S1b C2b C3b 111.7(2) yes
C3b C2b H2b 128.0(10) no
C2b C3b H3b 125.0(10) no
C2b C3b C4b 113.8(3) yes
C4b C3b H3b 121.0(10) no
C3b C4b C13b 121.3(2) yes
C3b C4b C5b 112.1(2) yes
C5b C4b C13b 126.6(2) yes
S1b C5b C4b 110.50(10) yes
C4b C5b C6b 129.6(2) yes
S1b C5b C6b 119.80(10) yes
S7b C6b C5b 121.50(10) yes
C5b C6b C10b 127.9(2) yes
S7b C6b C10b 110.50(10) yes
S7b C8b H8b 124(2) no
S7b C8b C9b 111.7(2) yes
C9b C8b H8b 125(2) no
C8b C9b H9b 123.0(10) no
C8b C9b C10b 113.3(2) yes
C10b C9b H9b 123.0(10) no
C6b C10b C9b 112.5(2) yes
C9b C10b C11b 124.2(2) yes
C6b C10b C11b 123.3(2) yes
O12b C11b C10b 112.7(2) yes
C10b C11b H112b 110(2) no
C10b C11b H111b 112.0(10) no
O12b C11b H112b 109(2) no
O12b C11b H111b 105.0(10) no
H111b C11b H112b 108(2) no
O12b C13b C4b 115.8(2) yes
C4b C13b H132b 111(2) no
C4b C13b H131b 109.0(10) no
O12b C13b H132b 107(2) no
O12b C13b H131b 109.0(10) no
H131b C13b H132b 104.0(10) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1a C2a 1.705(3) yes
S1a C5a 1.7280(10) yes
S7a C6a 1.7280(10) yes
S7a C8a 1.704(2) yes
O12a C11a 1.421(2) yes
O12a C13a 1.411(3) yes
C2a C3a 1.340(4) yes
C2a H2a 0.900(10) no
C3a C4a 1.419(2) yes
C3a H3a 0.920(10) no
C4a C5a 1.364(2) yes
C4a C13a 1.504(3) yes
C5a C6a 1.450(2) yes
C6a C10a 1.368(3) yes
C8a C9a 1.340(4) yes
C8a H8a 0.91(2) no
C9a C10a 1.409(3) yes
C9a H9a 0.84(2) no
C10a C11a 1.497(4) yes
C11a H111a 0.960(10) no
C11a H112a 0.920(10) no
C13a H131a 1.010(10) no
C13a H132a 0.950(10) no
S1b C2b 1.709(2) yes
S1b C5b 1.7360(10) yes
S7b C6b 1.7230(10) yes
S7b C8b 1.701(2) yes
O12b C11b 1.427(2) yes
O12b C13b 1.411(3) yes
C2b C3b 1.334(3) yes
C2b H2b 0.930(10) no
C3b C4b 1.420(3) yes
C3b H3b 0.940(10) no
C4b C5b 1.3660(10) yes
C4b C13b 1.498(3) yes
C5b C6b 1.450(2) yes
C6b C10b 1.366(2) yes
C8b C9b 1.344(3) yes
C8b H8b 0.98(2) no
C9b C10b 1.410(3) yes
C9b H9b 0.970(10) no
C10b C11b 1.492(2) yes
C11b H111b 0.950(10) no
C11b H112b 0.99(3) no
C13b H131b 0.880(10) no
C13b H132b 0.99(2) no