#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:53:49 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178410 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/31/4023135.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023135
loop_
_publ_author_name
'Flavio Cermola'
'Annalisa Guaragna'
'Maria Rosaria Iesce'
'Giovanni Palumbo'
'Raffaella Purcaro'
'Maria Rubino'
'Angela Tuzi'
_publ_section_title
;
 New Insight into the Reaction of Singlet Oxygen with
 Sulfur-Containing Cyclic Alkenes: Dye-Sensitized Photooxygenation of
 5,6-Dihydro-1,4-dithiins
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10075
_journal_page_last               10080
_journal_paper_doi               10.1021/jo701983v
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C13 H15 N O3 S2'
_chemical_formula_sum            'C13 H15 N O3 S2'
_chemical_formula_weight         297.38
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.505(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6835(6)
_cell_length_b                   14.492(2)
_cell_length_c                   12.632(3)
_cell_measurement_reflns_used    159
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.691
_cell_measurement_theta_min      4.616
_cell_volume                     1355.4(4)
_computing_cell_refinement       'Dirax/lsq (Duisenberg et al., 2000)'
_computing_data_collection       'Collect (Nonius B.V, 1999)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 1997)
;
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method
'CCD rotation images, thick slices phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10104
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.09
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.395
_exptl_absorpt_correction_T_max  0.8578
_exptl_absorpt_correction_T_min  0.7973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS (Bruker-Nonius, 2002).
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0429P)²+0.6813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                1941
_reflns_number_total             2380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701983v-File004.cif
_cod_data_source_block           cis-6d
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023135
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.7628(3) -0.11474(14) 0.98577(18) 0.0254(5) Uani 1 1 d .
H1A H 0.8657 -0.1458 1.0377 0.025 Uiso 1 1 calc R
H1B H 0.6967 -0.0779 1.0285 0.025 Uiso 1 1 calc R
C2 C 0.6386(3) -0.18528(14) 0.91578(19) 0.0252(5) Uani 1 1 d .
H2A H 0.5815 -0.2237 0.9619 0.025 Uiso 1 1 calc R
H2B H 0.7075 -0.2262 0.8789 0.025 Uiso 1 1 calc R
C3 C 0.6431(2) -0.04784(12) 0.77616(16) 0.0157(4) Uani 1 1 d .
C4 C 0.6971(2) -0.09934(12) 0.68350(16) 0.0164(4) Uani 1 1 d .
C5 C 0.8455(2) 0.04151(12) 0.63991(16) 0.0165(4) Uani 1 1 d .
C6 C 0.7370(3) 0.10105(14) 0.56476(18) 0.0231(5) Uani 1 1 d .
H6 H 0.6348 0.0783 0.5110 0.023 Uiso 1 1 calc R
C7 C 0.7790(3) 0.19412(14) 0.5688(2) 0.0309(5) Uani 1 1 d .
H7 H 0.7058 0.2354 0.5173 0.031 Uiso 1 1 calc R
C8 C 0.9275(3) 0.22714(14) 0.6476(2) 0.0333(6) Uani 1 1 d .
H8 H 0.9535 0.2913 0.6518 0.033 Uiso 1 1 calc R
C9 C 1.0377(3) 0.16696(15) 0.72020(19) 0.0303(5) Uani 1 1 d .
H9 H 1.1408 0.1898 0.7732 0.030 Uiso 1 1 calc R
C10 C 0.9990(3) 0.07322(14) 0.71646(17) 0.0217(4) Uani 1 1 d .
H10 H 1.0763 0.0315 0.7654 0.022 Uiso 1 1 calc R
C11 C 0.5375(3) 0.04295(13) 0.74246(18) 0.0204(4) Uani 1 1 d .
C12 C 0.5811(3) 0.12382(13) 0.8174(2) 0.0308(5) Uani 1 1 d .
H12A H 0.4885 0.1714 0.7930 0.031 Uiso 1 1 calc R
H12B H 0.6992 0.1487 0.8163 0.031 Uiso 1 1 calc R
H12C H 0.5844 0.1046 0.8923 0.031 Uiso 1 1 calc R
C13 C 0.8924(3) -0.10975(14) 0.56177(18) 0.0266(5) Uani 1 1 d .
H13A H 0.8851 -0.1756 0.5776 0.027 Uiso 1 1 calc R
H13B H 1.0195 -0.0915 0.5764 0.027 Uiso 1 1 calc R
H13C H 0.8307 -0.0980 0.4844 0.027 Uiso 1 1 calc R
O1 O 0.37737(19) -0.06257(10) 0.87929(13) 0.0302(4) Uani 1 1 d .
O2 O 0.41900(19) 0.04178(10) 0.65768(13) 0.0316(4) Uani 1 1 d .
O3 O 0.65248(17) -0.18062(8) 0.66583(12) 0.0226(3) Uani 1 1 d .
S1 S 0.84314(6) -0.04089(3) 0.89300(4) 0.01934(15) Uani 1 1 d .
S2 S 0.46856(6) -0.12290(3) 0.81512(4) 0.02106(15) Uani 1 1 d .
N1 N 0.8059(2) -0.05613(10) 0.63188(14) 0.0178(4) Uani 1 1 d .
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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 S1 106.97(15)
C2 C1 H1A 110.3
S1 C1 H1A 110.3
C2 C1 H1B 110.3
S1 C1 H1B 110.3
H1A C1 H1B 108.6
C1 C2 S2 107.36(14)
C1 C2 H2A 110.2
S2 C2 H2A 110.2
C1 C2 H2B 110.2
S2 C2 H2B 110.2
H2A C2 H2B 108.5
C4 C3 C11 115.65(16)
C4 C3 S1 107.58(12)
C11 C3 S1 116.24(13)
C4 C3 S2 105.88(12)
C11 C3 S2 101.83(11)
S1 C3 S2 108.87(10)
O3 C4 N1 122.48(17)
O3 C4 C3 118.98(16)
N1 C4 C3 118.23(15)
C6 C5 C10 120.99(18)
C6 C5 N1 119.03(17)
C10 C5 N1 119.77(17)
C7 C6 C5 119.4(2)
C7 C6 H6 120.3
C5 C6 H6 120.3
C8 C7 C6 120.2(2)
C8 C7 H7 119.9
C6 C7 H7 119.9
C9 C8 C7 120.08(19)
C9 C8 H8 120.0
C7 C8 H8 120.0
C8 C9 C10 120.5(2)
C8 C9 H9 119.7
C10 C9 H9 119.7
C5 C10 C9 118.8(2)
C5 C10 H10 120.6
C9 C10 H10 120.6
O2 C11 C12 124.35(18)
O2 C11 C3 116.68(17)
C12 C11 C3 118.91(18)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
N1 C13 H13A 109.5
N1 C13 H13B 109.5
H13A C13 H13B 109.5
N1 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C1 S1 C3 97.55(9)
O1 S2 C2 105.56(10)
O1 S2 C3 105.88(8)
C2 S2 C3 92.38(9)
C4 N1 C5 124.63(15)
C4 N1 C13 119.20(15)
C5 N1 C13 116.17(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.512(3)
C1 S1 1.813(2)
C1 H1A 0.9900
C1 H1B 0.9900
C2 S2 1.803(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.536(3)
C3 C11 1.545(3)
C3 S1 1.8272(19)
C3 S2 1.8912(18)
C4 O3 1.230(2)
C4 N1 1.344(2)
C5 C6 1.385(3)
C5 C10 1.389(3)
C5 N1 1.445(2)
C6 C7 1.385(3)
C6 H6 0.9500
C7 C8 1.384(3)
C7 H7 0.9500
C8 C9 1.379(3)
C8 H8 0.9500
C9 C10 1.389(3)
C9 H9 0.9500
C10 H10 0.9500
C11 O2 1.206(2)
C11 C12 1.487(3)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 N1 1.465(2)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
O1 S2 1.4886(15)
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
S1 C1 C2 S2 -54.42(16)
C11 C3 C4 O3 -125.28(18)
S1 C3 C4 O3 102.91(17)
S2 C3 C4 O3 -13.4(2)
C11 C3 C4 N1 60.9(2)
S1 C3 C4 N1 -70.91(18)
S2 C3 C4 N1 172.80(13)
C10 C5 C6 C7 -2.4(3)
N1 C5 C6 C7 -177.02(18)
C5 C6 C7 C8 -0.4(3)
C6 C7 C8 C9 2.2(3)
C7 C8 C9 C10 -1.3(3)
C6 C5 C10 C9 3.2(3)
N1 C5 C10 C9 177.84(17)
C8 C9 C10 C5 -1.4(3)
C4 C3 C11 O2 43.5(2)
S1 C3 C11 O2 171.13(14)
S2 C3 C11 O2 -70.74(19)
C4 C3 C11 C12 -139.26(18)
S1 C3 C11 C12 -11.7(2)
S2 C3 C11 C12 106.49(17)
C2 C1 S1 C3 31.18(15)
C4 C3 S1 C1 -113.32(13)
C11 C3 S1 C1 115.19(15)
S2 C3 S1 C1 0.99(11)
C1 C2 S2 O1 -58.53(15)
C1 C2 S2 C3 48.67(15)
C4 C3 S2 O1 -163.69(12)
C11 C3 S2 O1 -42.39(15)
S1 C3 S2 O1 80.90(11)
C4 C3 S2 C2 89.40(14)
C11 C3 S2 C2 -149.31(14)
S1 C3 S2 C2 -26.01(11)
O3 C4 N1 C5 172.45(18)
C3 C4 N1 C5 -14.0(3)
O3 C4 N1 C13 -7.5(3)
C3 C4 N1 C13 166.14(17)
C6 C5 N1 C4 -90.7(2)
C10 C5 N1 C4 94.6(2)
C6 C5 N1 C13 89.2(2)
C10 C5 N1 C13 -85.5(2)
