# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_266HRM16
_audit_block_doi                 10.5517/ccdc.csd.cc1n4blq
_database_code_depnum_ccdc_archive 'CCDC 1523513'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7OB01853C 2017
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(R,R)-3-(2-methylpropane-2-sulfinylamino)-2,2-dimethyl-3-phenylpropanoic acid'
_chemical_name_common            ?
_chemical_melting_point          413-416
_chemical_formula_moiety         'C15 H23 N O3 S'
_chemical_formula_sum            'C15 H23 N O3 S'
_chemical_formula_weight         297.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   18.7982(16)
_cell_length_b                   6.0423(5)
_cell_length_c                   14.3040(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.908(4)
_cell_angle_gamma                90
_cell_volume                     1589.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      68.32

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    1.867
_shelx_estimated_absorpt_T_min   0.702
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.7874
_exptl_absorpt_correction_T_max  0.8892
_exptl_absorpt_process_details   'SHELXTL (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12570
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.0955
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.157
_diffrn_reflns_theta_max         68.311
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2874
_reflns_number_gt                2647
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_max     0.963
_reflns_Friedel_fraction_full    0.966

_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       'APEX3 v2016.1 (Bruker, 2014)'
_computing_cell_refinement       'APEX3 v2016.1 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.37A  (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2014 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_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)+(0.0252P)²+1.7462P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1028 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.01(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2874
_refine_ls_number_parameters     192
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_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 0.66019(4) 0.49569(14) 0.22708(5) 0.0252(2) Uani 1 1 d . . . . .
O1 O 0.78625(17) 0.4543(5) 0.48731(19) 0.0439(8) Uani 1 1 d . . . . .
O2 O 0.86993(16) 0.2027(5) 0.54617(19) 0.0388(7) Uani 1 1 d D . . . .
H2 H 0.859(2) 0.222(8) 0.6008(18) 0.047 Uiso 1 1 d D U . . .
O3 O 0.65470(15) 0.7061(5) 0.28044(19) 0.0345(7) Uani 1 1 d . . . . .
N1 N 0.71685(16) 0.3190(5) 0.2941(2) 0.0262(7) Uani 1 1 d D . . . .
H1 H 0.708(2) 0.310(7) 0.3533(14) 0.031 Uiso 1 1 d D U . . .
C1 C 0.8285(2) 0.3135(6) 0.4758(3) 0.0283(8) Uani 1 1 d . . . . .
C2 C 0.8445(2) 0.2454(7) 0.3787(3) 0.0268(8) Uani 1 1 d . . . . .
C3 C 0.79434(19) 0.3795(6) 0.2980(2) 0.0235(8) Uani 1 1 d . . . . .
H3 H 0.8004 0.5403 0.3143 0.028 Uiso 1 1 calc R U . . .
C4 C 0.8365(2) -0.0060(8) 0.3653(3) 0.0357(8) Uani 1 1 d . . . . .
H4A H 0.8683 -0.0812 0.4188 0.054 Uiso 1 1 calc R U . . .
H4B H 0.8500 -0.0488 0.3053 0.054 Uiso 1 1 calc R U . . .
H4C H 0.7859 -0.0486 0.3635 0.054 Uiso 1 1 calc R U . . .
C5 C 0.9239(2) 0.3133(8) 0.3811(3) 0.0390(10) Uani 1 1 d . . . . .
H5A H 0.9297 0.4722 0.3941 0.059 Uiso 1 1 calc R U . . .
H5B H 0.9363 0.2803 0.3193 0.059 Uiso 1 1 calc R U . . .
H5C H 0.9564 0.2305 0.4316 0.059 Uiso 1 1 calc R U . . .
C6 C 0.81219(19) 0.3455(6) 0.2003(3) 0.0253(8) Uani 1 1 d . . . . .
C7 C 0.85269(18) 0.5043(8) 0.1648(2) 0.0292(7) Uani 1 1 d . . . . .
H7 H 0.8673 0.6340 0.2012 0.035 Uiso 1 1 calc R U . . .
C8 C 0.8723(2) 0.4779(9) 0.0772(3) 0.0364(9) Uani 1 1 d . . . . .
H8 H 0.9002 0.5889 0.0542 0.044 Uiso 1 1 calc R U . . .
C9 C 0.8516(2) 0.2916(8) 0.0237(3) 0.0359(10) Uani 1 1 d . . . . .
H9 H 0.8656 0.2719 -0.0359 0.043 Uiso 1 1 calc R U . . .
C10 C 0.8099(2) 0.1318(7) 0.0573(3) 0.0344(9) Uani 1 1 d . . . . .
H10 H 0.7948 0.0033 0.0202 0.041 Uiso 1 1 calc R U . . .
C11 C 0.7904(2) 0.1596(7) 0.1446(3) 0.0290(8) Uani 1 1 d . . . . .
H11 H 0.7616 0.0500 0.1668 0.035 Uiso 1 1 calc R U . . .
C12 C 0.5741(2) 0.3440(7) 0.2212(3) 0.0297(8) Uani 1 1 d . . . . .
C13 C 0.5775(2) 0.1498(8) 0.1556(3) 0.0425(11) Uani 1 1 d . . . . .
H13A H 0.6161 0.0483 0.1858 0.064 Uiso 1 1 calc R U . . .
H13B H 0.5878 0.2033 0.0951 0.064 Uiso 1 1 calc R U . . .
H13C H 0.5308 0.0718 0.1433 0.064 Uiso 1 1 calc R U . . .
C14 C 0.5637(2) 0.2693(8) 0.3185(3) 0.0446(11) Uani 1 1 d . . . . .
H14A H 0.5153 0.2036 0.3125 0.067 Uiso 1 1 calc R U . . .
H14B H 0.5683 0.3968 0.3617 0.067 Uiso 1 1 calc R U . . .
H14C H 0.6008 0.1590 0.3444 0.067 Uiso 1 1 calc R U . . .
C15 C 0.5157(2) 0.5092(9) 0.1751(3) 0.0440(10) Uani 1 1 d . . . . .
H15A H 0.5248 0.5556 0.1130 0.066 Uiso 1 1 calc R U . . .
H15B H 0.5170 0.6388 0.2166 0.066 Uiso 1 1 calc R U . . .
H15C H 0.4677 0.4390 0.1661 0.066 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 O3 1.497(3) . ?
S1 N1 1.665(3) . ?
S1 C12 1.846(4) . ?
O1 C1 1.198(5) . ?
O2 C1 1.321(5) . ?
O2 H2 0.858(14) . ?
N1 C3 1.492(4) . ?
N1 H1 0.899(13) . ?
C1 C2 1.537(5) . ?
C2 C4 1.534(6) . ?
C2 C5 1.543(5) . ?
C2 C3 1.558(5) . ?
C3 C6 1.516(5) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.385(5) . ?
C6 C11 1.390(5) . ?
C7 C8 1.387(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.371(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C14 1.513(6) . ?
C12 C13 1.513(6) . ?
C12 C15 1.530(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
O3 S1 N1 110.75(16) . . ?
O3 S1 C12 107.02(17) . . ?
N1 S1 C12 99.11(17) . . ?
C1 O2 H2 114(3) . . ?
C3 N1 S1 111.6(2) . . ?
C3 N1 H1 110(3) . . ?
S1 N1 H1 111(3) . . ?
O1 C1 O2 123.9(4) . . ?
O1 C1 C2 125.0(3) . . ?
O2 C1 C2 111.0(3) . . ?
C4 C2 C1 110.2(3) . . ?
C4 C2 C5 109.6(3) . . ?
C1 C2 C5 106.1(3) . . ?
C4 C2 C3 113.2(3) . . ?
C1 C2 C3 109.2(3) . . ?
C5 C2 C3 108.3(3) . . ?
N1 C3 C6 109.4(3) . . ?
N1 C3 C2 109.7(3) . . ?
C6 C3 C2 113.4(3) . . ?
N1 C3 H3 108.1 . . ?
C6 C3 H3 108.1 . . ?
C2 C3 H3 108.1 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 117.9(3) . . ?
C7 C6 C3 119.1(3) . . ?
C11 C6 C3 122.9(3) . . ?
C6 C7 C8 121.4(4) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 120.0(4) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 119.5(4) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C6 121.0(4) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C14 C12 C13 111.7(4) . . ?
C14 C12 C15 112.0(4) . . ?
C13 C12 C15 110.9(3) . . ?
C14 C12 S1 112.6(3) . . ?
C13 C12 S1 105.3(3) . . ?
C15 C12 S1 103.9(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
O3 S1 N1 C3 -77.5(3) . . . . ?
C12 S1 N1 C3 170.3(2) . . . . ?
O1 C1 C2 C4 -127.8(4) . . . . ?
O2 C1 C2 C4 54.9(4) . . . . ?
O1 C1 C2 C5 113.7(4) . . . . ?
O2 C1 C2 C5 -63.7(4) . . . . ?
O1 C1 C2 C3 -2.8(5) . . . . ?
O2 C1 C2 C3 179.8(3) . . . . ?
S1 N1 C3 C6 -68.0(3) . . . . ?
S1 N1 C3 C2 167.1(2) . . . . ?
C4 C2 C3 N1 58.7(4) . . . . ?
C1 C2 C3 N1 -64.5(4) . . . . ?
C5 C2 C3 N1 -179.6(3) . . . . ?
C4 C2 C3 C6 -64.0(4) . . . . ?
C1 C2 C3 C6 172.9(3) . . . . ?
C5 C2 C3 C6 57.8(4) . . . . ?
N1 C3 C6 C7 136.8(3) . . . . ?
C2 C3 C6 C7 -100.4(4) . . . . ?
N1 C3 C6 C11 -44.0(5) . . . . ?
C2 C3 C6 C11 78.8(4) . . . . ?
C11 C6 C7 C8 -1.2(6) . . . . ?
C3 C6 C7 C8 178.0(4) . . . . ?
C6 C7 C8 C9 0.0(6) . . . . ?
C7 C8 C9 C10 1.0(6) . . . . ?
C8 C9 C10 C11 -0.8(6) . . . . ?
C9 C10 C11 C6 -0.4(6) . . . . ?
C7 C6 C11 C10 1.4(5) . . . . ?
C3 C6 C11 C10 -177.8(4) . . . . ?
O3 S1 C12 C14 -65.7(3) . . . . ?
N1 S1 C12 C14 49.4(3) . . . . ?
O3 S1 C12 C13 172.4(3) . . . . ?
N1 S1 C12 C13 -72.5(3) . . . . ?
O3 S1 C12 C15 55.7(3) . . . . ?
N1 S1 C12 C15 170.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 S1 0.858(14) 2.90(3) 3.628(3) 143(4) 4_646
O2 H2 O3 0.858(14) 1.772(18) 2.615(4) 167(5) 4_646
N1 H1 O1 0.899(13) 2.33(3) 2.919(4) 123(3) .

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.052



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/Hexane '
_chemical_compound_source        'Organic synthesis'
