#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:55:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180455 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/24/7212432.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_7212432
loop_
_publ_author_name
'Brondel, Nicolas'
'Moynihan, Eamonn J. A.'
'Lehane, K. Niamh'
'Eccles, Kevin S.'
'Elcoate, Curtis J.'
'Coles, Simon J.'
'Lawrence, Simon E.'
'Maguire, Anita R.'
_publ_section_title
;
 Does intermolecular SO⋯H--C--SO hydrogen bonding
 in sulfoxides and sulfones provide a robust supramolecular synthon in the
 solid state?
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              2910
_journal_paper_doi               10.1039/c000371a
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C15 H16 O2 S'
_chemical_formula_sum            'C15 H16 O2 S'
_chemical_formula_weight         260.34
_chemical_name_systematic
;
?
;
_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                 90.494(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.458(3)
_cell_length_b                   5.4558(6)
_cell_length_c                   8.0849(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.32
_cell_measurement_theta_min      8.46
_cell_volume                     1343.4(2)
_computing_cell_refinement       'Nonius MACH3'
_computing_data_collection       'Nonius MACH3'
_computing_data_reduction        'PLATON (Spek, 2002)'
_computing_molecular_graphics    'PLATON (Spek, 2002)'
_computing_publication_material  'SHELXL-97; PLATON'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Nonius MACH3'
_diffrn_measurement_method       'ω-2θ 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  0.0805
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3712
_diffrn_reflns_theta_full        25.51
_diffrn_reflns_theta_max         25.51
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        0
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0357P)²+0.6900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.1069
_reflns_number_gt                1702
_reflns_number_total             2500
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c000371a.txt
_cod_data_source_block           compound_02
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7212432
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 0.46535(8) -0.2489(6) 0.4149(4) 0.0748(8) Uani 1 1 d .
H1A H 0.4521 -0.2567 0.5220 0.112 Uiso 1 1 calc R
H1B H 0.4967 -0.2392 0.4274 0.112 Uiso 1 1 calc R
H1C H 0.4578 -0.3932 0.3529 0.112 Uiso 1 1 calc R
O2 O 0.44985(5) -0.0384(4) 0.3296(2) 0.0671(5) Uani 1 1 d .
C3 C 0.40572(7) -0.0259(4) 0.2922(3) 0.0481(6) Uani 1 1 d .
C4 C 0.39295(8) 0.1698(5) 0.1937(3) 0.0574(6) Uani 1 1 d .
H4 H 0.4139 0.2807 0.1568 0.069 Uiso 1 1 calc R
C5 C 0.34961(8) 0.2011(4) 0.1501(3) 0.0530(6) Uani 1 1 d .
H5 H 0.3414 0.3349 0.0855 0.064 Uiso 1 1 calc R
C6 C 0.31780(7) 0.0355(4) 0.2012(3) 0.0447(5) Uani 1 1 d .
C7 C 0.33103(8) -0.1608(4) 0.2982(3) 0.0519(6) Uani 1 1 d .
H7 H 0.3103 -0.2744 0.3330 0.062 Uiso 1 1 calc R
C8 C 0.37476(7) -0.1908(4) 0.3443(3) 0.0504(6) Uani 1 1 d .
H8 H 0.3830 -0.3226 0.4105 0.060 Uiso 1 1 calc R
S9 S 0.26322(2) 0.08675(14) 0.13171(8) 0.0624(2) Uani 1 1 d .
C10 C 0.23047(7) -0.0766(5) 0.2805(3) 0.0576(6) Uani 1 1 d .
H10A H 0.2375 -0.2500 0.2776 0.069 Uiso 1 1 calc R
H10B H 0.2366 -0.0157 0.3911 0.069 Uiso 1 1 calc R
C11 C 0.18272(7) -0.0376(4) 0.2369(3) 0.0469(6) Uani 1 1 d .
C12 C 0.15945(8) 0.1612(4) 0.2954(3) 0.0510(6) Uani 1 1 d .
H12 H 0.1735 0.2738 0.3641 0.061 Uiso 1 1 calc R
C13 C 0.11567(8) 0.1968(4) 0.2542(3) 0.0494(6) Uani 1 1 d .
H13 H 0.1006 0.3315 0.2955 0.059 Uiso 1 1 calc R
C14 C 0.09448(7) 0.0311(4) 0.1514(2) 0.0443(5) Uani 1 1 d .
C15 C 0.11738(8) -0.1677(4) 0.0907(3) 0.0500(6) Uani 1 1 d .
H15 H 0.1034 -0.2787 0.0205 0.060 Uiso 1 1 calc R
C16 C 0.16094(8) -0.2020(5) 0.1338(3) 0.0507(6) Uani 1 1 d .
H16 H 0.1759 -0.3373 0.0931 0.061 Uiso 1 1 calc R
O17 O 0.05130(5) 0.0488(3) 0.1008(2) 0.0607(5) Uani 1 1 d .
C18 C 0.02695(8) 0.2567(6) 0.1545(4) 0.0713(8) Uani 1 1 d .
H18A H 0.0257 0.2575 0.2731 0.107 Uiso 1 1 calc R
H18B H -0.0023 0.2490 0.1095 0.107 Uiso 1 1 calc R
H18C H 0.0411 0.4037 0.1171 0.107 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 O2 C1 117.8(2)
C8 C3 O2 124.9(2)
C8 C3 C4 119.4(2)
O2 C3 C4 115.7(2)
C5 C4 C3 120.5(2)
C4 C5 C6 120.9(2)
C7 C6 C5 118.1(2)
C7 C6 S9 124.68(18)
C5 C6 S9 117.22(18)
C6 C7 C8 121.1(2)
C3 C8 C7 120.0(2)
C6 S9 C10 103.48(10)
C11 C10 S9 108.20(15)
C12 C11 C16 117.9(2)
C12 C11 C10 121.8(2)
C16 C11 C10 120.2(2)
C11 C12 C13 121.6(2)
C14 C13 C12 119.7(2)
O17 C14 C15 115.7(2)
O17 C14 C13 124.9(2)
C15 C14 C13 119.5(2)
C16 C15 C14 120.2(2)
C15 C16 C11 121.1(2)
C14 O17 C18 117.63(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.418(3)
O2 C3 1.377(3)
C3 C8 1.372(3)
C3 C4 1.386(3)
C4 C5 1.374(3)
C5 C6 1.390(3)
C6 C7 1.385(3)
C6 S9 1.772(2)
C7 C8 1.390(3)
S9 C10 1.804(2)
C10 C11 1.508(3)
C11 C12 1.381(3)
C11 C16 1.389(3)
C12 C13 1.385(3)
C13 C14 1.384(3)
C14 O17 1.377(2)
C14 C15 1.382(3)
C15 C16 1.382(3)
O17 C18 1.425(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
C1 O2 C3 C8 6.4(3)
C1 O2 C3 C4 -173.3(2)
C8 C3 C4 C5 0.9(4)
O2 C3 C4 C5 -179.4(2)
C3 C4 C5 C6 -1.1(4)
C4 C5 C6 C7 0.4(3)
C4 C5 C6 S9 -177.73(19)
C5 C6 C7 C8 0.5(3)
S9 C6 C7 C8 178.49(18)
O2 C3 C8 C7 -179.6(2)
C4 C3 C8 C7 0.0(3)
C6 C7 C8 C3 -0.7(4)
C7 C6 S9 C10 23.8(2)
C5 C6 S9 C10 -158.22(19)
C6 S9 C10 C11 177.90(17)
S9 C10 C11 C12 -87.4(2)
S9 C10 C11 C16 91.8(2)
C16 C11 C12 C13 0.4(3)
C10 C11 C12 C13 179.6(2)
C11 C12 C13 C14 -0.4(3)
C12 C13 C14 O17 -179.3(2)
C12 C13 C14 C15 -0.2(3)
O17 C14 C15 C16 179.9(2)
C13 C14 C15 C16 0.7(3)
C14 C15 C16 C11 -0.7(3)
C12 C11 C16 C15 0.1(3)
C10 C11 C16 C15 -179.1(2)
C15 C14 O17 C18 -177.3(2)
C13 C14 O17 C18 1.9(3)
