# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_wh11
_database_code_depnum_ccdc_archive 'CCDC 1923345'
loop_
_audit_author_name
_audit_author_address
'He Wang'
;School of Chemistry and Materials Science, Liaoning Shihua University
China
;
_audit_update_record             
;
2019-06-17 deposited with the CCDC.	2019-10-25 downloaded from the CCDC.
;
_chemical_name_systematic        diphenyl(1-tosylcyclopropyl)methanol
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 O3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         378.46

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3828(19)
_cell_length_b                   11.548(2)
_cell_length_c                   14.490(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.392(10)
_cell_angle_gamma                90
_cell_volume                     1904.1(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4259
_cell_measurement_theta_min      2.2604
_cell_measurement_theta_max      24.0970
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.230
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800

_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            14632
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         25.12
_diffrn_reflns_theta_full        25.12
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             3376
_reflns_number_gt                2216
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1198
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_number_reflns         3376
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+0.4169P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.306
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.41686(5) 0.48660(5) 0.74423(5) 0.0505(2) Uani d . . . 1 . .
O O1 0.58872(14) 0.37657(15) 0.59971(12) 0.0564(5) Uani d . . . 1 . .
H H1 0.596085 0.43076 0.635961 0.085 Uiso calc U . R 1 . .
O O2 0.53092(15) 0.53685(14) 0.72874(13) 0.0628(5) Uani d . . . 1 . .
O O3 0.31751(16) 0.56300(15) 0.74648(14) 0.0713(6) Uani d . . . 1 . .
C C1 0.3968(2) 0.1307(2) 0.54575(17) 0.0527(7) Uani d . . . 1 . .
H H1A 0.370483 0.10511 0.602464 0.063 Uiso calc U . R 1 . .
C C2 0.3698(2) 0.0680(2) 0.4671(2) 0.0627(8) Uani d . . . 1 . .
H H2 0.323903 0.001674 0.471364 0.075 Uiso calc U . R 1 . .
C C3 0.4097(3) 0.1019(3) 0.3828(2) 0.0672(8) Uani d . . . 1 . .
H H3 0.391853 0.058836 0.330072 0.081 Uiso calc U . R 1 . .
C C4 0.4761(3) 0.2002(3) 0.37782(19) 0.0681(8) Uani d . . . 1 . .
H H4 0.504254 0.223916 0.321151 0.082 Uiso calc U . R 1 . .
C C5 0.5018(2) 0.2644(2) 0.45578(18) 0.0573(7) Uani d . . . 1 . .
H H5 0.546376 0.331494 0.450739 0.069 Uiso calc U . R 1 . .
C C6 0.4625(2) 0.2312(2) 0.54149(16) 0.0429(6) Uani d . . . 1 . .
C C7 0.53381(18) 0.22680(19) 0.70753(15) 0.0382(6) Uani d . . . 1 . .
C C8 0.6525(2) 0.2125(2) 0.72775(18) 0.0544(7) Uani d . . . 1 . .
H H8 0.707357 0.250731 0.69226 0.065 Uiso calc U . R 1 . .
C C9 0.6908(2) 0.1425(3) 0.7998(2) 0.0643(8) Uani d . . . 1 . .
H H9 0.770835 0.134511 0.812491 0.077 Uiso calc U . R 1 . .
C C10 0.6120(3) 0.0851(2) 0.8524(2) 0.0628(8) Uani d . . . 1 . .
H H10 0.637895 0.0379 0.900754 0.075 Uiso calc U . R 1 . .
C C11 0.4941(2) 0.0975(2) 0.83318(18) 0.0532(7) Uani d . . . 1 . .
H H11 0.439939 0.058209 0.868568 0.064 Uiso calc U . R 1 . .
C C12 0.4553(2) 0.16772(19) 0.76206(16) 0.0414(6) Uani d . . . 1 . .
H H12 0.374973 0.175676 0.750346 0.05 Uiso calc U . R 1 . .
C C13 0.49430(18) 0.3043(2) 0.62727(16) 0.0416(6) Uani d . . . 1 . .
C C14 0.39026(19) 0.38426(19) 0.65369(16) 0.0414(6) Uani d . . . 1 . .
C C15 0.2641(2) 0.3480(2) 0.64254(19) 0.0569(7) Uani d . . . 1 . .
H H15A 0.248157 0.270669 0.619251 0.068 Uiso calc U . R 1 . .
H H15B 0.209328 0.375495 0.687878 0.068 Uiso calc U . R 1 . .
C C16 0.3123(2) 0.4339(3) 0.5776(2) 0.0643(8) Uani d . . . 1 . .
H H16A 0.287174 0.513789 0.583539 0.077 Uiso calc U . R 1 . .
H H16B 0.326021 0.408915 0.51488 0.077 Uiso calc U . R 1 . .
C C17 0.4248(2) 0.41366(19) 0.85034(17) 0.0439(6) Uani d . . . 1 . .
C C18 0.3244(2) 0.3723(2) 0.89066(19) 0.0541(7) Uani d . . . 1 . .
H H18 0.251214 0.384052 0.862248 0.065 Uiso calc U . R 1 . .
C C19 0.3334(2) 0.3138(2) 0.97301(19) 0.0580(7) Uani d . . . 1 . .
H H19 0.265954 0.284447 0.999342 0.07 Uiso calc U . R 1 . .
C C20 0.4413(2) 0.2977(2) 1.01762(17) 0.0520(7) Uani d . . . 1 . .
C C21 0.5398(2) 0.3421(2) 0.97685(18) 0.0532(7) Uani d . . . 1 . .
H H21 0.612761 0.332985 1.006262 0.064 Uiso calc U . R 1 . .
C C22 0.5328(2) 0.3993(2) 0.89399(18) 0.0489(7) Uani d . . . 1 . .
H H22 0.600347 0.428142 0.867426 0.059 Uiso calc U . R 1 . .
C C23 0.4498(3) 0.2330(3) 1.1075(2) 0.0790(9) Uani d . . . 1 . .
H H23A 0.518541 0.184876 1.108266 0.119 Uiso calc U . R 1 . .
H H23B 0.381187 0.18557 1.113965 0.119 Uiso calc U . R 1 . .
H H23C 0.454953 0.287221 1.15763 0.119 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O3 . 1.4354(17) ?
S1 O2 . 1.4446(17) ?
S1 C17 . 1.754(3) ?
S1 C14 . 1.786(2) ?
O1 C13 . 1.425(2) ?
O1 H1 . 0.82 ?
C1 C2 . 1.379(3) ?
C1 C6 . 1.383(3) ?
C1 H1A . 0.93 ?
C2 C3 . 1.370(4) ?
C2 H2 . 0.93 ?
C3 C4 . 1.367(4) ?
C3 H3 . 0.93 ?
C4 C5 . 1.377(4) ?
C4 H4 . 0.93 ?
C5 C6 . 1.384(3) ?
C5 H5 . 0.93 ?
C6 C13 . 1.538(3) ?
C7 C8 . 1.385(3) ?
C7 C12 . 1.387(3) ?
C7 C13 . 1.527(3) ?
C8 C9 . 1.383(4) ?
C8 H8 . 0.93 ?
C9 C10 . 1.363(4) ?
C9 H9 . 0.93 ?
C10 C11 . 1.371(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.376(3) ?
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
C13 C14 . 1.557(3) ?
C14 C15 . 1.501(3) ?
C14 C16 . 1.511(3) ?
C15 C16 . 1.482(4) ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 C22 . 1.379(3) ?
C17 C18 . 1.381(3) ?
C18 C19 . 1.373(4) ?
C18 H18 . 0.93 ?
C19 C20 . 1.386(3) ?
C19 H19 . 0.93 ?
C20 C21 . 1.379(3) ?
C20 C23 . 1.502(4) ?
C21 C22 . 1.371(3) ?
C21 H21 . 0.93 ?
C22 H22 . 0.93 ?
C23 H23A . 0.96 ?
C23 H23B . 0.96 ?
C23 H23C . 0.96 ?

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
_geom_angle_publ_flag
O3 S1 O2 . . 117.92(12) ?
O3 S1 C17 . . 107.39(12) ?
O2 S1 C17 . . 107.58(11) ?
O3 S1 C14 . . 107.69(11) ?
O2 S1 C14 . . 106.78(11) ?
C17 S1 C14 . . 109.29(11) ?
C13 O1 H1 . . 109.5 ?
C2 C1 C6 . . 120.9(3) ?
C2 C1 H1A . . 119.5 ?
C6 C1 H1A . . 119.5 ?
C3 C2 C1 . . 121.0(3) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C4 C3 C2 . . 118.7(3) ?
C4 C3 H3 . . 120.7 ?
C2 C3 H3 . . 120.7 ?
C3 C4 C5 . . 120.7(3) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C4 C5 C6 . . 121.4(3) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C1 C6 C5 . . 117.3(2) ?
C1 C6 C13 . . 122.8(2) ?
C5 C6 C13 . . 119.9(2) ?
C8 C7 C12 . . 117.4(2) ?
C8 C7 C13 . . 119.9(2) ?
C12 C7 C13 . . 122.71(19) ?
C9 C8 C7 . . 121.1(3) ?
C9 C8 H8 . . 119.4 ?
C7 C8 H8 . . 119.4 ?
C10 C9 C8 . . 120.5(2) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C9 C10 C11 . . 119.3(3) ?
C9 C10 H10 . . 120.4 ?
C11 C10 H10 . . 120.4 ?
C10 C11 C12 . . 120.6(3) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C11 C12 C7 . . 121.1(2) ?
C11 C12 H12 . . 119.4 ?
C7 C12 H12 . . 119.4 ?
O1 C13 C7 . . 110.27(18) ?
O1 C13 C6 . . 105.00(18) ?
C7 C13 C6 . . 110.67(19) ?
O1 C13 C14 . . 107.76(18) ?
C7 C13 C14 . . 111.85(18) ?
C6 C13 C14 . . 111.03(18) ?
C15 C14 C16 . . 58.96(16) ?
C15 C14 C13 . . 122.7(2) ?
C16 C14 C13 . . 118.8(2) ?
C15 C14 S1 . . 114.10(18) ?
C16 C14 S1 . . 111.75(18) ?
C13 C14 S1 . . 117.17(15) ?
C16 C15 C14 . . 60.86(16) ?
C16 C15 H15A . . 117.7 ?
C14 C15 H15A . . 117.7 ?
C16 C15 H15B . . 117.7 ?
C14 C15 H15B . . 117.7 ?
H15A C15 H15B . . 114.8 ?
C15 C16 C14 . . 60.18(16) ?
C15 C16 H16A . . 117.8 ?
C14 C16 H16A . . 117.8 ?
C15 C16 H16B . . 117.8 ?
C14 C16 H16B . . 117.8 ?
H16A C16 H16B . . 114.9 ?
C22 C17 C18 . . 120.1(2) ?
C22 C17 S1 . . 119.1(2) ?
C18 C17 S1 . . 120.78(19) ?
C19 C18 C17 . . 119.5(2) ?
C19 C18 H18 . . 120.3 ?
C17 C18 H18 . . 120.3 ?
C18 C19 C20 . . 121.2(3) ?
C18 C19 H19 . . 119.4 ?
C20 C19 H19 . . 119.4 ?
C21 C20 C19 . . 118.1(3) ?
C21 C20 C23 . . 121.4(2) ?
C19 C20 C23 . . 120.6(3) ?
C22 C21 C20 . . 121.6(2) ?
C22 C21 H21 . . 119.2 ?
C20 C21 H21 . . 119.2 ?
C21 C22 C17 . . 119.5(2) ?
C21 C22 H22 . . 120.3 ?
C17 C22 H22 . . 120.3 ?
C20 C23 H23A . . 109.5 ?
C20 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C20 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?



