#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:20:13 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180388 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/57/7205785.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_7205785
loop_
_publ_author_name
'Jacob, C.'
'da Piedade, Fátima M.'
'Robalo, M. Paula'
'Duarte, M. Teresa'
_publ_section_title
;
 Evaluation of intermolecular interactions in thioxanthone derivatives:
 substituent effect on crystal diversity
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              2604
_journal_paper_doi               10.1039/c0ce00783h
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C13 H10 N2 O4 S'
_chemical_formula_weight         290.29
_chemical_name_systematic
;
?
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 121.757(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.309(4)
_cell_length_b                   6.7318(16)
_cell_length_c                   13.206(6)
_cell_measurement_temperature    293(2)
_cell_volume                     1232.8(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_av_sigmaI/netI    0.0857
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8278
_diffrn_reflns_theta_full        30.53
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  0.9781
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0485
_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)+(0.0330P)²+0.0574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                1228
_reflns_number_total             2016
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c0ce00783h.txt
_cod_data_source_block           compound2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_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_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      C2/m
_cod_database_code               7205785
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.16645(17) 0.5000 -0.1437(2) 0.0269(6) Uani 1 2 d S . .
H1A H 0.17057(19) 0.606(2) -0.1720(7) 0.032 Uiso 0.50 1 calc PR . .
H1B H 0.1715(2) 0.394(2) -0.1712(7) 0.032 Uiso 0.50 1 calc PR . .
C1 C 0.15114(19) 0.5000 -0.0503(2) 0.0194(6) Uani 1 2 d S . .
C2 C 0.14256(13) 0.3220(3) -0.00306(16) 0.0214(5) Uani 1 1 d . . .
H2 H 0.14829(18) 0.199(3) -0.0345(7) 0.026 Uiso 1 1 calc R . .
C3 C 0.12572(13) 0.3221(3) 0.08936(16) 0.0196(4) Uani 1 1 d . . .
H3 H 0.11950(19) 0.196(3) 0.1215(7) 0.023 Uiso 1 1 calc R . .
C4 C 0.11763(18) 0.5000 0.1366(2) 0.0173(6) Uani 1 2 d S . .
S1 S 0.08603(5) 0.5000 0.24626(6) 0.01785(18) Uani 1 2 d S . .
C7 C 0.19839(18) 0.5000 0.3810(2) 0.0154(6) Uani 1 2 d S . .
C8 C 0.28477(19) 0.5000 0.3812(2) 0.0183(6) Uani 1 2 d S . .
H8 H 0.2821(2) 0.5000 0.306(2) 0.022 Uiso 1 2 calc SR . .
C9 C 0.37298(19) 0.5000 0.4865(2) 0.0199(6) Uani 1 2 d S . .
H9 H 0.4275(17) 0.5000 0.4853(2) 0.024 Uiso 1 2 calc SR . .
C10 C 0.37751(18) 0.5000 0.5940(2) 0.0170(6) Uani 1 2 d S . .
N2 N 0.47189(16) 0.5000 0.7055(2) 0.0210(5) Uani 1 2 d S . .
O1 O 0.54473(14) 0.5000 0.69860(18) 0.0395(6) Uani 1 2 d S . .
O2 O 0.47471(13) 0.5000 0.79982(16) 0.0216(5) Uani 1 2 d S . .
C11 C 0.29541(19) 0.5000 0.5982(2) 0.0174(6) Uani 1 2 d S . .
H11 H 0.2995(2) 0.5000 0.667(2) 0.021 Uiso 1 2 calc SR . .
C12 C 0.20528(18) 0.5000 0.4926(2) 0.0152(6) Uani 1 2 d S . .
C13 C 0.11735(19) 0.5000 0.4996(2) 0.0163(6) Uani 1 2 d S . .
O3 O 0.03629(13) 0.5000 0.41042(16) 0.0248(5) Uani 1 2 d S . .
O4 O 0.13353(13) 0.5000 0.60812(15) 0.0216(5) Uani 1 2 d S . .
H4 H 0.0855 0.5404 0.6067 0.032 Uiso 0.50 1 calc PR . .
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
N1 C1 C2 120.56(12) . 6_565 ?
N1 C1 C2 120.56(12) . . ?
C2 C1 C2 118.9(2) 6_565 . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C3 119.2(2) . 6_565 ?
C3 C4 S1 120.24(12) . . ?
C3 C4 S1 120.24(12) 6_565 . ?
C7 S1 C4 103.31(12) . . ?
C8 C7 C12 117.8(2) . . ?
C8 C7 S1 120.7(2) . . ?
C12 C7 S1 121.48(18) . . ?
C9 C8 C7 121.0(2) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.0(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 N2 119.4(2) . . ?
C9 C10 N2 119.5(2) . . ?
O2 N2 O1 123.5(2) . . ?
O2 N2 C10 118.7(2) . . ?
O1 N2 C10 117.8(2) . . ?
C10 C11 C12 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C7 120.3(2) . . ?
C11 C12 C13 118.8(2) . . ?
C7 C12 C13 120.9(2) . . ?
O3 C13 O4 123.1(2) . . ?
O3 C13 C12 122.0(2) . . ?
O4 C13 C12 115.0(2) . . ?
C13 O4 H4 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.381(3) . ?
N1 H1A 0.8248 . ?
N1 H1B 0.8248 . ?
C1 C2 1.392(2) 6_565 ?
C1 C2 1.392(2) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(2) . ?
C3 H3 0.9771 . ?
C4 C3 1.388(2) 6_565 ?
C4 S1 1.775(2) . ?
S1 C7 1.758(3) . ?
C7 C8 1.408(3) . ?
C7 C12 1.417(3) . ?
C8 C9 1.377(4) . ?
C8 H8 0.9774 . ?
C9 C10 1.383(3) . ?
C9 H9 0.8978 . ?
C10 C11 1.369(3) . ?
C10 N2 1.467(3) . ?
N2 O2 1.222(3) . ?
N2 O1 1.238(3) . ?
C11 C12 1.396(4) . ?
C11 H11 0.8820 . ?
C12 C13 1.485(3) . ?
C13 O3 1.223(3) . ?
C13 O4 1.313(3) . ?
O4 H4 0.8200 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -179.0(2) . . . . ?
C2 C1 C2 C3 0.0(4) 6_565 . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C3 0.6(4) . . . 6_565 ?
C2 C3 C4 S1 174.68(16) . . . . ?
C3 C4 S1 C7 93.0(2) . . . . ?
C3 C4 S1 C7 -93.0(2) 6_565 . . . ?
C4 S1 C7 C8 0.0 . . . . ?
C4 S1 C7 C12 180.0 . . . . ?
C12 C7 C8 C9 0.0 . . . . ?
S1 C7 C8 C9 180.0 . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C8 C9 C10 N2 180.0 . . . . ?
C11 C10 N2 O2 0.0 . . . . ?
C9 C10 N2 O2 180.0 . . . . ?
C11 C10 N2 O1 180.0 . . . . ?
C9 C10 N2 O1 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
N2 C10 C11 C12 180.0 . . . . ?
C10 C11 C12 C7 0.0 . . . . ?
C10 C11 C12 C13 180.0 . . . . ?
C8 C7 C12 C11 0.0 . . . . ?
S1 C7 C12 C11 180.0 . . . . ?
C8 C7 C12 C13 180.0 . . . . ?
S1 C7 C12 C13 0.0 . . . . ?
C11 C12 C13 O3 180.0 . . . . ?
C7 C12 C13 O3 0.0 . . . . ?
C11 C12 C13 O4 0.0 . . . . ?
C7 C12 C13 O4 180.0 . . . . ?
