# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Diphenylsulfone
_database_code_depnum_ccdc_archive 'CCDC 1862593'
_audit_update_record             
;
2018-08-17 deposited with the CCDC.
2018-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 O2 S'
_chemical_formula_sum            'C12 H10 O2 S'
_chemical_formula_weight         218.26

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.272(5)
_cell_length_b                   7.645(6)
_cell_length_c                   12.120(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.36(3)
_cell_angle_gamma                90
_cell_volume                     1038.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      30.49

_exptl_crystal_description       Cube
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.286
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18545
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.226
_diffrn_reflns_theta_max         32.769
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.810
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.810
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3112
_reflns_number_gt                2706
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0386P)²+0.8595P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3112
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.75728(3) 0.14889(4) 0.82490(3) 0.01655(10) Uani 1 1 d . . . . .
O1 O 0.80591(9) 0.31895(14) 0.85235(10) 0.0245(2) Uani 1 1 d . . . . .
O2 O 0.76039(9) 0.07722(16) 0.70637(9) 0.0234(2) Uani 1 1 d . . . . .
C7 C 0.58936(12) 0.25402(19) 0.95338(12) 0.0181(3) Uani 1 1 d . . . . .
H7 H 0.649400 0.310519 0.998784 0.022 Uiso 1 1 calc R U . . .
C3 C 0.91340(11) -0.2438(2) 1.09492(13) 0.0217(3) Uani 1 1 d . . . . .
H3 H 0.944029 -0.326336 1.146785 0.026 Uiso 1 1 calc R U . . .
C11 C 0.53649(11) 0.06643(18) 0.78121(12) 0.0180(3) Uani 1 1 d . . . . .
H11 H 0.559251 0.004835 0.720822 0.022 Uiso 1 1 calc R U . . .
C5 C 0.86035(11) 0.05416(18) 1.04430(12) 0.0174(3) Uani 1 1 d . . . . .
H5 H 0.855299 0.171801 1.062745 0.021 Uiso 1 1 calc R U . . .
C8 C 0.47839(12) 0.25960(19) 0.97580(12) 0.0195(3) Uani 1 1 d . . . . .
H8 H 0.455782 0.317851 1.037505 0.023 Uiso 1 1 calc R U . . .
C6 C 0.81994(11) -0.00348(17) 0.92985(11) 0.0152(2) Uani 1 1 d . . . . .
C10 C 0.42555(12) 0.07562(19) 0.80404(13) 0.0210(3) Uani 1 1 d . . . . .
H10 H 0.365289 0.020245 0.758260 0.025 Uiso 1 1 calc R U . . .
C1 C 0.82506(11) -0.17931(18) 0.89706(12) 0.0182(3) Uani 1 1 d . . . . .
H1 H 0.799113 -0.215233 0.825109 0.022 Uiso 1 1 calc R U . . .
C12 C 0.61673(11) 0.15694(17) 0.85534(11) 0.0148(2) Uani 1 1 d . . . . .
C9 C 0.39684(12) 0.17229(19) 0.90080(13) 0.0201(3) Uani 1 1 d . . . . .
H9 H 0.317064 0.176065 0.913664 0.024 Uiso 1 1 calc R U . . .
C2 C 0.87256(12) -0.29993(19) 0.98089(14) 0.0220(3) Uani 1 1 d . . . . .
H2 H 0.877789 -0.417646 0.962703 0.026 Uiso 1 1 calc R U . . .
C4 C 0.90698(11) -0.0682(2) 1.12679(12) 0.0203(3) Uani 1 1 d . . . . .
H4 H 0.932175 -0.032699 1.199000 0.024 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
S1 O1 1.4356(14) . ?
S1 O2 1.5417(14) . ?
S1 C12 1.6671(15) . ?
S1 C6 1.8096(16) . ?
C7 C8 1.3098(19) . ?
C7 C12 1.463(2) . ?
C7 H7 0.9300 . ?
C3 C4 1.401(2) . ?
C3 C2 1.471(2) . ?
C3 H3 0.9300 . ?
C11 C10 1.3124(19) . ?
C11 C12 1.3870(19) . ?
C11 H11 0.9300 . ?
C5 C4 1.426(2) . ?
C5 C6 1.478(2) . ?
C5 H5 0.9300 . ?
C8 C9 1.390(2) . ?
C8 H8 0.9300 . ?
C6 C1 1.405(2) . ?
C10 C9 1.453(2) . ?
C10 H10 0.9300 . ?
C1 C2 1.431(2) . ?
C1 H1 0.9300 . ?
C9 H9 0.9300 . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?

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
O1 S1 O2 119.36(7) . . ?
O1 S1 C12 105.25(7) . . ?
O2 S1 C12 109.86(7) . . ?
O1 S1 C6 108.11(8) . . ?
O2 S1 C6 112.26(8) . . ?
C12 S1 C6 100.06(7) . . ?
C8 C7 C12 118.51(13) . . ?
C8 C7 H7 120.7 . . ?
C12 C7 H7 120.7 . . ?
C4 C3 C2 121.22(13) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C10 C11 C12 113.89(13) . . ?
C10 C11 H11 123.1 . . ?
C12 C11 H11 123.1 . . ?
C4 C5 C6 120.91(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C8 C9 115.23(14) . . ?
C7 C8 H8 122.4 . . ?
C9 C8 H8 122.4 . . ?
C1 C6 C5 122.19(12) . . ?
C1 C6 S1 116.24(11) . . ?
C5 C6 S1 121.55(11) . . ?
C11 C10 C9 120.01(13) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C6 C1 C2 116.07(14) . . ?
C6 C1 H1 122.0 . . ?
C2 C1 H1 122.0 . . ?
C11 C12 C7 126.74(12) . . ?
C11 C12 S1 113.94(11) . . ?
C7 C12 S1 119.32(10) . . ?
C8 C9 C10 125.59(13) . . ?
C8 C9 H9 117.2 . . ?
C10 C9 H9 117.2 . . ?
C1 C2 C3 122.15(14) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C3 C4 C5 117.47(14) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 H4 121.3 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C7 C8 C9 -0.9(2) . . . . ?
C4 C5 C6 C1 0.16(19) . . . . ?
C4 C5 C6 S1 178.53(9) . . . . ?
O1 S1 C6 C1 -154.29(10) . . . . ?
O2 S1 C6 C1 -20.56(12) . . . . ?
C12 S1 C6 C1 95.88(11) . . . . ?
O1 S1 C6 C5 27.25(12) . . . . ?
O2 S1 C6 C5 160.98(10) . . . . ?
C12 S1 C6 C5 -82.57(11) . . . . ?
C12 C11 C10 C9 -0.9(2) . . . . ?
C5 C6 C1 C2 -0.40(18) . . . . ?
S1 C6 C1 C2 -178.84(9) . . . . ?
C10 C11 C12 C7 1.3(2) . . . . ?
C10 C11 C12 S1 -178.77(11) . . . . ?
C8 C7 C12 C11 -0.4(2) . . . . ?
C8 C7 C12 S1 179.72(11) . . . . ?
O1 S1 C12 C11 142.54(11) . . . . ?
O2 S1 C12 C11 12.84(12) . . . . ?
C6 S1 C12 C11 -105.40(12) . . . . ?
O1 S1 C12 C7 -37.53(12) . . . . ?
O2 S1 C12 C7 -167.23(10) . . . . ?
C6 S1 C12 C7 74.53(13) . . . . ?
C7 C8 C9 C10 1.3(2) . . . . ?
C11 C10 C9 C8 -0.4(2) . . . . ?
C6 C1 C2 C3 0.18(19) . . . . ?
C4 C3 C2 C1 0.3(2) . . . . ?
C2 C3 C4 C5 -0.53(19) . . . . ?
C6 C5 C4 C3 0.31(18) . . . . ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.067



