# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1585785'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
(2S,4S)-1-benzyl-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-(tosylamine)pyrrolidine 
;
_chemical_absolute_configuration rm
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H30 N2 O4 S'
_chemical_formula_weight         430.55

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'
N N 0.0061 0.0033 '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           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   9.7197(6)
_cell_length_b                   12.3037(5)
_cell_length_c                   19.6860(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2354.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3322
_cell_measurement_theta_min      3.4600
_cell_measurement_theta_max      21.2480

_exptl_crystal_description       prims
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89277
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27289
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0748
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         31.12
_reflns_number_total             6801
_reflns_number_gt                3460
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0333P)²+0.3580P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_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(9)
_refine_ls_number_reflns         6801
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1471
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_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
S1 S 0.62360(11) 0.52209(6) 0.91798(5) 0.0787(3) Uani 1 1 d . . .
O1 O 0.5743(4) 0.48210(19) 0.98204(12) 0.1218(11) Uani 1 1 d . . .
O2 O 0.7568(3) 0.4931(2) 0.89372(16) 0.1241(11) Uani 1 1 d . . .
O3 O 0.2514(2) 0.36001(13) 0.85482(9) 0.0584(5) Uani 1 1 d . . .
O4 O 0.2440(3) 0.18626(16) 0.82308(13) 0.1138(10) Uani 1 1 d . . .
N1 N 0.2997(2) 0.54821(14) 0.76912(10) 0.0461(5) Uani 1 1 d . . .
N2 N 0.5121(3) 0.48537(18) 0.86319(11) 0.0617(6) Uani 1 1 d . . .
HN2 H 0.4389 0.4540 0.8780 0.074 Uiso 1 1 calc R . .
C1 C 0.4373(3) 0.5938(2) 0.76461(14) 0.0509(7) Uani 1 1 d . . .
H1A H 0.4469 0.6575 0.7933 0.061 Uiso 1 1 calc R . .
H1B H 0.4605 0.6129 0.7182 0.061 Uiso 1 1 calc R . .
C2 C 0.5244(3) 0.5008(2) 0.79003(13) 0.0546(7) Uani 1 1 d . . .
H2 H 0.6209 0.5106 0.7769 0.065 Uiso 1 1 calc R . .
C3 C 0.4610(3) 0.4047(2) 0.75262(15) 0.0566(7) Uani 1 1 d . . .
H3A H 0.4715 0.3383 0.7786 0.068 Uiso 1 1 calc R . .
H3B H 0.5037 0.3950 0.7085 0.068 Uiso 1 1 calc R . .
C4 C 0.3074(3) 0.43519(18) 0.74506(13) 0.0482(7) Uani 1 1 d . . .
H4 H 0.2821 0.4327 0.6969 0.058 Uiso 1 1 calc R . .
C5 C 0.2101(3) 0.36385(19) 0.78498(14) 0.0524(7) Uani 1 1 d . . .
H5 H 0.1164 0.3927 0.7816 0.063 Uiso 1 1 calc R . .
C6 C 0.2115(4) 0.2442(2) 0.76342(16) 0.0691(9) Uani 1 1 d . . .
H6A H 0.1222 0.2225 0.7461 0.083 Uiso 1 1 calc R . .
H6B H 0.2802 0.2316 0.7286 0.083 Uiso 1 1 calc R . .
C7 C 0.2207(4) 0.2534(2) 0.87932(16) 0.0681(9) Uani 1 1 d . . .
C8 C 0.0769(4) 0.2469(3) 0.90601(19) 0.0945(12) Uani 1 1 d . . .
H8A H 0.0673 0.2948 0.9442 0.142 Uiso 1 1 calc R . .
H8B H 0.0577 0.1737 0.9199 0.142 Uiso 1 1 calc R . .
H8C H 0.0135 0.2680 0.8710 0.142 Uiso 1 1 calc R . .
C9 C 0.3255(4) 0.2263(4) 0.9334(2) 0.1254(16) Uani 1 1 d . . .
H9A H 0.3102 0.2713 0.9725 0.188 Uiso 1 1 calc R . .
H9B H 0.4164 0.2391 0.9160 0.188 Uiso 1 1 calc R . .
H9C H 0.3165 0.1512 0.9460 0.188 Uiso 1 1 calc R . .
C10 C 0.1933(3) 0.6156(2) 0.73776(14) 0.0580(8) Uani 1 1 d . . .
H10A H 0.1085 0.5743 0.7343 0.070 Uiso 1 1 calc R . .
H10B H 0.2216 0.6356 0.6922 0.070 Uiso 1 1 calc R . .
C11 C 0.1683(3) 0.7164(2) 0.77885(14) 0.0501(7) Uani 1 1 d . . .
C12 C 0.1748(3) 0.8189(2) 0.75032(15) 0.0579(7) Uani 1 1 d . . .
H12 H 0.1958 0.8261 0.7044 0.069 Uiso 1 1 calc R . .
C13 C 0.1506(3) 0.9113(2) 0.7890(2) 0.0718(9) Uani 1 1 d . . .
H13 H 0.1564 0.9797 0.7692 0.086 Uiso 1 1 calc R . .
C14 C 0.1185(4) 0.9017(3) 0.8558(2) 0.0843(10) Uani 1 1 d . . .
H14 H 0.1007 0.9635 0.8816 0.101 Uiso 1 1 calc R . .
C15 C 0.1122(4) 0.8007(3) 0.88533(17) 0.0802(9) Uani 1 1 d . . .
H15 H 0.0919 0.7943 0.9313 0.096 Uiso 1 1 calc R . .
C16 C 0.1359(3) 0.7089(2) 0.84718(15) 0.0660(8) Uani 1 1 d . . .
H16 H 0.1301 0.6408 0.8676 0.079 Uiso 1 1 calc R . .
C17 C 0.6196(3) 0.6650(2) 0.92298(12) 0.0524(7) Uani 1 1 d . . .
C18 C 0.7417(3) 0.7222(2) 0.92673(14) 0.0640(8) Uani 1 1 d . . .
H18 H 0.8253 0.6863 0.9215 0.077 Uiso 1 1 calc R . .
C19 C 0.7390(4) 0.8331(3) 0.93835(15) 0.0747(9) Uani 1 1 d . . .
H19 H 0.8216 0.8710 0.9410 0.090 Uiso 1 1 calc R . .
C20 C 0.6178(5) 0.8883(2) 0.94608(15) 0.0748(9) Uani 1 1 d . . .
C21 C 0.4959(4) 0.8300(3) 0.94012(14) 0.0713(9) Uani 1 1 d . . .
H21 H 0.4123 0.8663 0.9436 0.086 Uiso 1 1 calc R . .
C22 C 0.4969(3) 0.7199(2) 0.92917(13) 0.0616(8) Uani 1 1 d . . .
H22 H 0.4142 0.6822 0.9259 0.074 Uiso 1 1 calc R . .
C23 C 0.6154(6) 1.0092(3) 0.9613(2) 0.1330(17) Uani 1 1 d . . .
H23A H 0.7080 1.0362 0.9634 0.199 Uiso 1 1 calc R . .
H23B H 0.5707 1.0214 1.0041 0.199 Uiso 1 1 calc R . .
H23C H 0.5661 1.0465 0.9260 0.199 Uiso 1 1 calc R . .


_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 O2 1.425(3) . ?
S1 O1 1.436(3) . ?
S1 N2 1.594(2) . ?
S1 C17 1.762(3) . ?
O3 C7 1.429(3) . ?
O3 C5 1.433(3) . ?
O4 C7 1.400(3) . ?
O4 C6 1.410(3) . ?
N1 C1 1.453(3) . ?
N1 C10 1.462(3) . ?
N1 C4 1.471(3) . ?
N2 C2 1.457(3) . ?
N2 HN2 0.8600 . ?
C1 C2 1.509(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.522(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.547(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.511(4) . ?
C4 H4 0.9800 . ?
C5 C6 1.533(3) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.495(4) . ?
C7 C9 1.511(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.501(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.382(3) . ?
C11 C16 1.384(4) . ?
C12 C13 1.389(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.356(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.376(4) . ?
C17 C18 1.382(4) . ?
C18 C19 1.384(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.390(5) . ?
C20 C23 1.518(4) . ?
C21 C22 1.372(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
O2 S1 O1 120.8(2) . . ?
O2 S1 N2 108.65(14) . . ?
O1 S1 N2 105.68(16) . . ?
O2 S1 C17 106.77(17) . . ?
O1 S1 C17 106.59(14) . . ?
N2 S1 C17 107.80(13) . . ?
C7 O3 C5 107.2(2) . . ?
C7 O4 C6 108.9(2) . . ?
C1 N1 C10 114.0(2) . . ?
C1 N1 C4 107.4(2) . . ?
C10 N1 C4 115.8(2) . . ?
C2 N2 S1 125.2(2) . . ?
C2 N2 HN2 117.4 . . ?
S1 N2 HN2 117.4 . . ?
N1 C1 C2 101.7(2) . . ?
N1 C1 H1A 111.4 . . ?
C2 C1 H1A 111.4 . . ?
N1 C1 H1B 111.4 . . ?
C2 C1 H1B 111.4 . . ?
H1A C1 H1B 109.3 . . ?
N2 C2 C1 112.3(2) . . ?
N2 C2 C3 110.1(2) . . ?
C1 C2 C3 101.6(2) . . ?
N2 C2 H2 110.8 . . ?
C1 C2 H2 110.8 . . ?
C3 C2 H2 110.8 . . ?
C2 C3 C4 104.4(2) . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
N1 C4 C5 110.5(2) . . ?
N1 C4 C3 104.3(2) . . ?
C5 C4 C3 114.4(2) . . ?
N1 C4 H4 109.2 . . ?
C5 C4 H4 109.2 . . ?
C3 C4 H4 109.2 . . ?
O3 C5 C4 110.1(2) . . ?
O3 C5 C6 103.4(2) . . ?
C4 C5 C6 114.1(2) . . ?
O3 C5 H5 109.7 . . ?
C4 C5 H5 109.7 . . ?
C6 C5 H5 109.7 . . ?
O4 C6 C5 104.9(2) . . ?
O4 C6 H6A 110.8 . . ?
C5 C6 H6A 110.8 . . ?
O4 C6 H6B 110.8 . . ?
C5 C6 H6B 110.8 . . ?
H6A C6 H6B 108.8 . . ?
O4 C7 O3 104.0(2) . . ?
O4 C7 C8 113.4(3) . . ?
O3 C7 C8 111.3(3) . . ?
O4 C7 C9 108.5(3) . . ?
O3 C7 C9 107.5(3) . . ?
C8 C7 C9 111.8(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 110.8(2) . . ?
N1 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C16 117.8(3) . . ?
C12 C11 C10 121.9(2) . . ?
C16 C11 C10 120.3(2) . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.9(3) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C22 C17 C18 119.4(2) . . ?
C22 C17 S1 120.9(2) . . ?
C18 C17 S1 119.5(2) . . ?
C17 C18 C19 119.6(3) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 121.6(3) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 117.9(3) . . ?
C19 C20 C23 121.4(4) . . ?
C21 C20 C23 120.6(4) . . ?
C22 C21 C20 121.1(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C17 120.3(3) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
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 . . ?

_diffrn_measured_fraction_theta_max 0.924
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.033
