#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:02:04 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179552 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/21/4502108.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_4502108
loop_
_publ_author_name
'Eccles, Kevin S.'
'Elcoate, Curtis J.'
'Stokes, Stephen P.'
'Maguire, Anita R.'
'Lawrence, Simon E.'
_publ_section_title
;
 Sulfoxides: Potent Co-Crystal Formers
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4243
_journal_paper_doi               10.1021/cg1010192
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C14 H14 O S . C7 H6 N2 S. C7 H6 N2 S'
_chemical_formula_sum            'C28 H26 N4 O S3'
_chemical_formula_weight         530.71
_chemical_melting_point          90.5(15)
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2010.1-2'
_cell_angle_alpha                90
_cell_angle_beta                 106.798(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.475(6)
_cell_length_b                   7.7430(16)
_cell_length_c                   12.448(3)
_cell_measurement_reflns_used    6223
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      26.4233
_cell_measurement_theta_min      2.7346
_cell_volume                     2627.4(10)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2009, 7, 0, 0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 1997) 
Mercury 2.3 (Macrae et al. 2008)
;
_computing_publication_material  'SHELXL-97; Ortep-3 for Windows; Mercury 2.3'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX II DUO'
_diffrn_measurement_method       'φ & ω  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  0.0974
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            28880
_diffrn_reflns_theta_full        27.11
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.311
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0491
_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)+(0.0320P)²+5.6220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1234
_reflns_number_gt                2129
_reflns_number_total             2832
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg1010192_si_002.cif
_cod_data_source_block           Compound_3d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '89-92' was changed to '90.5(15)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2627.4(9)
_cod_database_code               4502108
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_refinement_flags
_atom_site_occupancy
S S1 0.00523(5) 0.14320(16) 0.71070(10) 0.0351(3) Uani d P 0.5
O O2 0 -0.0286(3) 0.75 0.0451(7) Uani d S 1
C C3 0.04631(13) 0.2677(4) 0.8177(3) 0.0617(10) Uani d . 1
H H3A 0.0536 0.3759 0.7833 0.074 Uiso calc R 1
H H3B 0.0291 0.3001 0.8734 0.074 Uiso calc R 1
C C4 0.09395(11) 0.1855(4) 0.8791(2) 0.0413(7) Uani d . 1
C C5 0.09816(11) 0.0801(3) 0.9711(2) 0.0407(6) Uani d . 1
H H5 0.0698 0.0529 0.9935 0.049 Uiso calc R 1
C C6 0.14334(14) 0.0136(4) 1.0310(3) 0.0626(10) Uani d . 1
H H6 0.1457 -0.0574 1.0945 0.075 Uiso calc R 1
C C7 0.18429(16) 0.0488(7) 0.9999(4) 0.0897(15) Uani d . 1
H H7 0.215 0.0026 1.0417 0.108 Uiso calc R 1
C C8 0.18126(16) 0.1505(7) 0.9085(5) 0.0918(16) Uani d . 1
H H8 0.2099 0.1746 0.8866 0.11 Uiso calc R 1
C C9 0.13607(16) 0.2190(5) 0.8472(3) 0.0692(11) Uani d . 1
H H9 0.1341 0.289 0.7833 0.083 Uiso calc R 1
N N21 0.00000(9) 0.3118(3) 0.1032(2) 0.0398(6) Uani d . 1
H H21A -0.0087(11) 0.238(4) 0.138(3) 0.052(10) Uiso d . 1
H H21B -0.0200(11) 0.369(4) 0.052(3) 0.046(8) Uiso d . 1
C C22 0.04778(9) 0.3489(3) 0.12621(19) 0.0316(5) Uani d . 1
S S23 0.09120(2) 0.24502(9) 0.23908(5) 0.03574(18) Uani d . 1
C C24 0.13746(9) 0.3617(4) 0.2057(2) 0.0361(6) Uani d . 1
C C25 0.18758(10) 0.3580(4) 0.2574(2) 0.0471(7) Uani d . 1
H H25 0.201 0.2869 0.3211 0.057 Uiso calc R 1
C C26 0.21756(11) 0.4606(5) 0.2140(3) 0.0578(9) Uani d . 1
H H26 0.252 0.4616 0.2487 0.069 Uiso calc R 1
C C27 0.19744(11) 0.5626(5) 0.1193(3) 0.0578(9) Uani d . 1
H H27 0.2186 0.6307 0.0898 0.069 Uiso calc R 1
C C28 0.14731(11) 0.5667(4) 0.0675(2) 0.0460(7) Uani d . 1
H H28 0.1341 0.6364 0.003 0.055 Uiso calc R 1
C C29 0.11662(9) 0.4671(3) 0.1115(2) 0.0340(6) Uani d . 1
N N30 0.06579(7) 0.4608(3) 0.06946(16) 0.0313(5) Uani d . 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O2 S1 C3 . 2_556 115.17(15)
O2 S1 C3 . . 110.87(12)
C3 S1 C3 2_556 . 100.9(2)
C4 C3 S1 . . 117.1(2)
C4 C3 H3A . . 108.0
S1 C3 H3A . . 108.0
C4 C3 H3B . . 108.0
S1 C3 H3B . . 108.0
H3A C3 H3B . . 107.3
C5 C4 C9 . . 118.1(3)
C5 C4 C3 . . 121.6(3)
C9 C4 C3 . . 120.3(3)
C4 C5 C6 . . 120.6(3)
C4 C5 H5 . . 119.7
C6 C5 H5 . . 119.7
C7 C6 C5 . . 120.8(4)
C7 C6 H6 . . 119.6
C5 C6 H6 . . 119.6
C6 C7 C8 . . 120.0(4)
C6 C7 H7 . . 120.0
C8 C7 H7 . . 120.0
C7 C8 C9 . . 120.0(4)
C7 C8 H8 . . 120.0
C9 C8 H8 . . 120.0
C4 C9 C8 . . 120.4(4)
C4 C9 H9 . . 119.8
C8 C9 H9 . . 119.8
C22 N21 H21A . . 119.(2)
C22 N21 H21B . . 118.(2)
H21A N21 H21B . . 123.(3)
N30 C22 N21 . . 123.9(2)
N30 C22 S23 . . 115.74(18)
N21 C22 S23 . . 120.3(2)
C24 S23 C22 . . 88.74(12)
C25 C24 C29 . . 121.8(3)
C25 C24 S23 . . 128.8(2)
C29 C24 S23 . . 109.41(19)
C26 C25 C24 . . 118.4(3)
C26 C25 H25 . . 120.8
C24 C25 H25 . . 120.8
C25 C26 C27 . . 120.3(3)
C25 C26 H26 . . 119.8
C27 C26 H26 . . 119.8
C28 C27 C26 . . 121.5(3)
C28 C27 H27 . . 119.3
C26 C27 H27 . . 119.3
C27 C28 C29 . . 118.9(3)
C27 C28 H28 . . 120.6
C29 C28 H28 . . 120.6
N30 C29 C28 . . 125.1(2)
N30 C29 C24 . . 115.8(2)
C28 C29 C24 . . 119.1(2)
C22 N30 C29 . . 110.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 O2 . 1.440(3)
S1 C3 2_556 1.705(4)
S1 C3 . 1.780(3)
C3 C4 . 1.494(4)
C3 H3A . 0.99
C3 H3B . 0.99
C4 C5 . 1.383(4)
C4 C9 . 1.393(5)
C5 C6 . 1.386(4)
C5 H5 . 0.95
C6 C7 . 1.358(6)
C6 H6 . 0.95
C7 C8 . 1.366(7)
C7 H7 . 0.95
C8 C9 . 1.397(6)
C8 H8 . 0.95
C9 H9 . 0.95
N21 C22 . 1.338(3)
N21 H21A . 0.80(3)
N21 H21B . 0.85(3)
C22 N30 . 1.312(3)
C22 S23 . 1.774(2)
S23 C24 . 1.744(3)
C24 C25 . 1.386(4)
C24 C29 . 1.411(3)
C25 C26 . 1.385(4)
C25 H25 . 0.95
C26 C27 . 1.396(5)
C26 H26 . 0.95
C27 C28 . 1.387(4)
C27 H27 . 0.95
C28 C29 . 1.392(4)
C28 H28 . 0.95
C29 N30 . 1.390(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N21 H21A O2 5_556 0.80(3) 2.10(3) 2.854(3) 156.(3)
N21 H21B N30 5_565 0.85(3) 2.14(3) 2.984(3) 173.(3)
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_site_symmetry_1
_geom_torsion
O2 S1 C3 C4 . 47.5(3)
C3 S1 C3 C4 2_556 169.9(4)
S1 C3 C4 C5 . -85.6(3)
S1 C3 C4 C9 . 96.9(3)
C9 C4 C5 C6 . 1.5(4)
C3 C4 C5 C6 . -176.0(3)
C4 C5 C6 C7 . -0.8(5)
C5 C6 C7 C8 . -0.1(6)
C6 C7 C8 C9 . 0.3(6)
C5 C4 C9 C8 . -1.4(5)
C3 C4 C9 C8 . 176.2(3)
C7 C8 C9 C4 . 0.5(6)
N30 C22 S23 C24 . -0.5(2)
N21 C22 S23 C24 . 179.5(2)
C22 S23 C24 C25 . 180.0(3)
C22 S23 C24 C29 . -0.89(19)
C29 C24 C25 C26 . -0.4(4)
S23 C24 C25 C26 . 178.6(2)
C24 C25 C26 C27 . -1.0(5)
C25 C26 C27 C28 . 1.1(6)
C26 C27 C28 C29 . 0.2(5)
C27 C28 C29 N30 . 178.9(3)
C27 C28 C29 C24 . -1.6(4)
C25 C24 C29 N30 . -178.7(2)
S23 C24 C29 N30 . 2.1(3)
C25 C24 C29 C28 . 1.7(4)
S23 C24 C29 C28 . -177.5(2)
N21 C22 N30 C29 . -178.3(2)
S23 C22 N30 C29 . 1.7(3)
C28 C29 N30 C22 . 177.1(3)
C24 C29 N30 C22 . -2.5(3)
