Does intermolecular SO⋯H–C–SO hydrogen bonding in sulfoxides and sulfones provide a robust supramolecular synthon in the solid state?
Brondel, Nicolas; Moynihan, Eamonn J. A.; Lehane, K. Niamh; Eccles, Kevin S.; Elcoate, Curtis J.; Coles, Simon J.; Lawrence, Simon E.; Maguire, Anita R.; CrystEngComm 12 (2010) 2910–; doi:10.1039/c000371a

data_7212444
_publ_section_title
;
 Does intermolecular S&#xE001;O&#x22EF;H--C--S&#xE001;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_absolute_configuration ad
_chemical_formula_moiety         'C15 H16 O3 S'
_chemical_formula_sum            'C15 H16 O3 S'
_chemical_formula_weight         276.34
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2009.7-0'
_cell_angle_alpha                90
_cell_angle_beta                 105.124(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.4234(11)
_cell_length_b                   5.4410(4)
_cell_length_c                   8.1642(5)
_cell_measurement_reflns_used    3560
_cell_measurement_temperature    180.(2)
_cell_measurement_theta_max      27.0188
_cell_measurement_theta_min      2.7360
_cell_volume                     661.40(8)
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2009, 7, 0, 0'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2002)'
_computing_publication_material  'SHELXL--97; PLATON'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      180.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       '\f & \w 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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5584
_diffrn_reflns_theta_full        27.09
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs Version 2008/1'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.211
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2873
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0349
_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/[\s^2^(Fo^2^)+(0.0545P)^2^+0.1685P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0922
_reflns_number_gt                2753
_reflns_number_total             2873
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c000371a.txt
_cod_data_source_block           compound_17
_cod_original_sg_symbol_Hall     ' P -2yc'
_cod_database_code               7212444