# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_iw0205n8
_database_code_depnum_ccdc_archive 'CCDC 1565482'
_audit_update_record             
;
2017-07-28 deposited with the CCDC.
2017-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'1-(((1R, 2R)-2-(tert-butoxy)cyclopropyl)sulfonyl)-4-methylbenzene'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 O3 S'
_chemical_formula_weight         268.36

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2'

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

_cell_length_a                   16.720(7)
_cell_length_b                   9.987(4)
_cell_length_c                   8.832(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.306(9)
_cell_angle_gamma                90.00
_cell_volume                     1474.7(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    6948
_cell_measurement_theta_min      2.3059
_cell_measurement_theta_max      28.6970

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.9154
_exptl_absorpt_correction_T_max  0.9732
_exptl_absorpt_process_details   
;
CrystalClear-SM 1.3.6 SP3 r6 (Rigaku/MSC, Inc., 2006)
;
_exptl_special_details           
;
????
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_device_type  
;
AFC7R, 4-circle diffractometer with Mercury CCD camera(Rigaku Corp.)
;
_diffrn_measurement_method       
;
Oscillation method with Fine-Slice process
;
_diffrn_detector_area_resol_mean 14.7059
_diffrn_reflns_number            13131
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         28.46
_reflns_number_total             3152
_reflns_number_gt                2455
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_structure_solution    'SIR2004 (Burla, Caliandro et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0894P)²+0.1485P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_number_reflns         3152
_refine_ls_number_parameters     167
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.31046(15) 0.1806(3) 0.5962(3) 0.0606(7) Uani 1 1 d . . .
H1 H 0.3033 0.2677 0.6454 0.073 Uiso 1 1 calc R . .
C2 C 0.35668(15) 0.0776(3) 0.6860(3) 0.0634(7) Uani 1 1 d . . .
H2 H 0.3413 -0.0166 0.6749 0.076 Uiso 1 1 calc R . .
C3 C 0.39560(15) 0.1446(5) 0.5546(3) 0.0816(10) Uani 1 1 d . . .
H3 H 0.4038 0.0920 0.4636 0.098 Uiso 1 1 calc R . .
H3A H 0.4371 0.2099 0.5759 0.098 Uiso 1 1 calc R . .
C4 C 0.14846(14) 0.1141(3) 0.5781(3) 0.0564(6) Uani 1 1 d . . .
C5 C 0.10392(19) 0.2234(4) 0.6154(4) 0.0744(8) Uani 1 1 d . . .
H5 H 0.1194 0.3086 0.5847 0.089 Uiso 1 1 calc R . .
C6 C 0.0348(2) 0.2054(5) 0.7003(4) 0.0852(11) Uani 1 1 d . . .
H6 H 0.0047 0.2796 0.7283 0.102 Uiso 1 1 calc R . .
C7 C 0.01016(16) 0.0794(4) 0.7434(3) 0.0712(9) Uani 1 1 d . . .
C8 C 0.05593(18) -0.0287(4) 0.7059(4) 0.0716(8) Uani 1 1 d . . .
H8 H 0.0400 -0.1139 0.7356 0.086 Uiso 1 1 calc R . .
C9 C 0.12606(16) -0.0129(3) 0.6238(3) 0.0626(7) Uani 1 1 d . . .
H9 H 0.1574 -0.0868 0.5999 0.075 Uiso 1 1 calc R . .
C10 C -0.06661(18) 0.0607(6) 0.8318(4) 0.0991(14) Uani 1 1 d . . .
H10 H -0.1104 0.0480 0.7626 0.149 Uiso 1 1 calc R . .
H10A H -0.0763 0.1387 0.8926 0.149 Uiso 1 1 calc R . .
H10B H -0.0617 -0.0164 0.8961 0.149 Uiso 1 1 calc R . .
C11 C 0.34587(17) 0.0750(4) 0.9605(3) 0.0681(8) Uani 1 1 d . . .
C12 C 0.2595(2) 0.1008(9) 0.9485(5) 0.160(3) Uani 1 1 d . . .
H12 H 0.2509 0.1917 0.9172 0.240 Uiso 1 1 calc R . .
H12A H 0.2350 0.0864 1.0452 0.240 Uiso 1 1 calc R . .
H12B H 0.2363 0.0411 0.8753 0.240 Uiso 1 1 calc R . .
C13 C 0.3662(6) -0.0693(6) 0.9775(7) 0.163(3) Uani 1 1 d . . .
H13 H 0.3714 -0.1093 0.8792 0.244 Uiso 1 1 calc R . .
H13A H 0.3246 -0.1138 1.0324 0.244 Uiso 1 1 calc R . .
H13B H 0.4158 -0.0778 1.0319 0.244 Uiso 1 1 calc R . .
C14 C 0.3854(3) 0.1515(8) 1.0830(4) 0.129(2) Uani 1 1 d . . .
H14 H 0.4400 0.1229 1.0927 0.193 Uiso 1 1 calc R . .
H14A H 0.3580 0.1360 1.1766 0.193 Uiso 1 1 calc R . .
H14B H 0.3839 0.2453 1.0592 0.193 Uiso 1 1 calc R . .
S1 S 0.23532(3) 0.13364(7) 0.46743(6) 0.0575(2) Uani 1 1 d . . .
O1 O 0.38743(10) 0.1189(3) 0.82459(18) 0.0703(5) Uani 1 1 d . . .
O2 O 0.25629(12) 0.0060(2) 0.4041(2) 0.0686(6) Uani 1 1 d . . .
O3 O 0.22227(13) 0.2429(2) 0.3645(2) 0.0730(6) Uani 1 1 d . . .


_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
C1 C2 1.509(4) . ?
C1 C3 1.515(4) . ?
C1 S1 1.754(3) . ?
C1 H1 0.9800 . ?
C2 O1 1.388(3) . ?
C2 C3 1.492(4) . ?
C2 H2 0.9800 . ?
C3 H3 0.9700 . ?
C3 H3A 0.9700 . ?
C4 C5 1.363(5) . ?
C4 C9 1.383(4) . ?
C4 S1 1.766(3) . ?
C5 C6 1.393(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.365(5) . ?
C7 C10 1.517(4) . ?
C8 C9 1.391(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C11 O1 1.458(3) . ?
C11 C12 1.470(5) . ?
C11 C14 1.477(5) . ?
C11 C13 1.488(7) . ?
C12 H12 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C13 H13 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C14 H14 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
S1 O3 1.436(2) . ?
S1 O2 1.436(2) . ?

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
C2 C1 C3 59.1(2) . . ?
C2 C1 S1 121.4(2) . . ?
C3 C1 S1 116.7(2) . . ?
C2 C1 H1 115.8 . . ?
C3 C1 H1 115.8 . . ?
S1 C1 H1 115.8 . . ?
O1 C2 C3 113.1(3) . . ?
O1 C2 C1 116.6(3) . . ?
C3 C2 C1 60.7(2) . . ?
O1 C2 H2 117.9 . . ?
C3 C2 H2 117.9 . . ?
C1 C2 H2 117.9 . . ?
C2 C3 C1 60.24(17) . . ?
C2 C3 H3 117.7 . . ?
C1 C3 H3 117.7 . . ?
C2 C3 H3A 117.7 . . ?
C1 C3 H3A 117.7 . . ?
H3 C3 H3A 114.9 . . ?
C5 C4 C9 121.0(3) . . ?
C5 C4 S1 119.8(2) . . ?
C9 C4 S1 119.2(2) . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 C10 120.3(4) . . ?
C6 C7 C10 120.6(3) . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C8 119.1(3) . . ?
C4 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C7 C10 H10 109.5 . . ?
C7 C10 H10A 109.5 . . ?
H10 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C11 C12 111.1(3) . . ?
O1 C11 C14 103.5(3) . . ?
C12 C11 C14 113.4(4) . . ?
O1 C11 C13 105.3(4) . . ?
C12 C11 C13 113.7(5) . . ?
C14 C11 C13 109.0(5) . . ?
C11 C12 H12 109.5 . . ?
C11 C12 H12A 109.5 . . ?
H12 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C13 H13 109.5 . . ?
C11 C13 H13A 109.5 . . ?
H13 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C14 H14 109.5 . . ?
C11 C14 H14A 109.5 . . ?
H14 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 S1 O2 117.68(12) . . ?
O3 S1 C1 108.25(14) . . ?
O2 S1 C1 108.31(14) . . ?
O3 S1 C4 108.17(14) . . ?
O2 S1 C4 108.70(13) . . ?
C1 S1 C4 105.01(11) . . ?
C2 O1 C11 117.5(2) . . ?

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
C3 C1 C2 O1 102.8(3) . . . . ?
S1 C1 C2 O1 -152.79(19) . . . . ?
S1 C1 C2 C3 104.4(3) . . . . ?
O1 C2 C3 C1 -108.6(3) . . . . ?
S1 C1 C3 C2 -112.3(2) . . . . ?
C9 C4 C5 C6 -0.3(5) . . . . ?
S1 C4 C5 C6 178.7(3) . . . . ?
C4 C5 C6 C7 -1.5(5) . . . . ?
C5 C6 C7 C8 2.0(5) . . . . ?
C5 C6 C7 C10 -178.1(3) . . . . ?
C6 C7 C8 C9 -0.7(5) . . . . ?
C10 C7 C8 C9 179.4(3) . . . . ?
C5 C4 C9 C8 1.5(4) . . . . ?
S1 C4 C9 C8 -177.5(2) . . . . ?
C7 C8 C9 C4 -1.0(5) . . . . ?
C2 C1 S1 O3 -160.3(2) . . . . ?
C3 C1 S1 O3 -91.7(3) . . . . ?
C2 C1 S1 O2 -31.6(2) . . . . ?
C3 C1 S1 O2 36.9(3) . . . . ?
C2 C1 S1 C4 84.4(2) . . . . ?
C3 C1 S1 C4 152.9(3) . . . . ?
C5 C4 S1 O3 -32.9(3) . . . . ?
C9 C4 S1 O3 146.1(2) . . . . ?
C5 C4 S1 O2 -161.7(2) . . . . ?
C9 C4 S1 O2 17.3(3) . . . . ?
C5 C4 S1 C1 82.5(3) . . . . ?
C9 C4 S1 C1 -98.4(2) . . . . ?
C3 C2 O1 C11 171.1(3) . . . . ?
C1 C2 O1 C11 103.6(3) . . . . ?
C12 C11 O1 C2 -49.6(5) . . . . ?
C14 C11 O1 C2 -171.7(4) . . . . ?
C13 C11 O1 C2 73.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        28.46
_diffrn_measured_fraction_theta_full 0.947
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.043
_chemical_absolute_configuration ad

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
