# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# 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_y0121m
_database_code_depnum_ccdc_archive 'CCDC 1046182'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;
_audit_creation_date             2015-02-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         '0.22(C13 H23 N O3 S)'
_chemical_formula_sum            'C2.889 H5.111 N0.222 O0.667 S0.222'
_chemical_formula_weight         60.76
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           ' P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   10.291(2)
_cell_length_b                   5.9808(12)
_cell_length_c                   12.068(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.531(3)
_cell_angle_gamma                90
_cell_volume                     722.1(3)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    4213
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.35
_cell_measurement_temperature    273(2)
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_min  0.845984
_exptl_absorpt_process_details   
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0532 before and 0.0281 after correction.
The Ratio of minimum to maximum transmission is 0.8460.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.2573
_exptl_crystal_density_meas      .
_exptl_crystal_F_000             296.3836
_exptl_crystal_description       pillar
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4174
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.74
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.9880
_diffrn_measured_fraction_theta_max 0.9880
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.784
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                2517
_reflns_number_total             2522
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.3993
_refine_diff_density_min         -0.3000
_refine_diff_density_rms         0.0707
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             11.7328
_refine_ls_goodness_of_fit_ref   1.0660
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2522
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.0660
_refine_ls_shift/su_max          0.0014
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0670P)²+0.0874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0880
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C16(H16a,H16b)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C10(H10)
2.d Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c), C8(H8a,H8b,H8c), C13(H13a,H13b,H13c), C15(H15a,H15b,H15c),
 C17(H17a,H17b,H17c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
S1 S -0.619319(3) -0.037804(3) -0.447119(3) 0.02109(8) Uani 1.000000 .
O0AA O -0.572465(3) 0.007992(3) -0.553855(3) 0.02656(15) Uani 1.000000 .
N3 N -0.526355(3) 0.106118(3) -0.338996(3) 0.02441(16) Uani 1.000000 .
H3 H -0.543894(3) 0.242958(3) -0.326131(3) 0.02929(19) Uiso 1.000000 R
O4 O -0.695603(3) 0.038524(3) -0.034600(3) 0.04299(16) Uani 1.000000 .
C5 C -0.411560(3) -0.014557(3) -0.266010(3) 0.02417(16) Uani 1.000000 .
H5 H -0.379868(3) -0.126468(3) -0.312867(3) 0.02901(19) Uiso 1.000000 R
C6 C -0.837635(3) 0.060333(3) -0.365468(3) 0.03509(18) Uani 1.000000 .
H6a H -0.845088(4) -0.099262(3) -0.361120(4) 0.0526(3) Uiso 1.000000 GR
H6b H -0.780922(4) 0.115378(4) -0.296074(3) 0.0526(3) Uiso 1.000000 GR
H6c H -0.924674(4) 0.126518(4) -0.376139(4) 0.0526(3) Uiso 1.000000 GR
C7 C -0.627934(3) -0.060557(3) -0.087758(3) 0.02877(17) Uani 1.000000 .
C8 C -0.755765(3) 0.371087(3) -0.472948(3) 0.02914(18) Uani 1.000000 .
H8a H -0.711083(4) 0.426971(3) -0.399311(3) 0.0437(3) Uiso 1.000000 GR
H8b H -0.701826(4) 0.399655(3) -0.526434(4) 0.0437(3) Uiso 1.000000 GR
H8c H -0.840474(3) 0.444722(3) -0.497859(4) 0.0437(3) Uiso 1.000000 GR
C9 C -0.298191(3) 0.152302(3) -0.221973(3) 0.03045(18) Uani 1.000000 .
H9a H -0.289150(3) 0.248743(3) -0.284358(3) 0.0365(2) Uiso 1.000000 R
H9b H -0.322358(3) 0.245618(3) -0.164181(3) 0.0365(2) Uiso 1.000000 R
C10 C -0.553140(3) -0.316026(3) -0.195732(3) 0.02859(18) Uani 1.000000 .
H10 H -0.546278(3) -0.439792(3) -0.240668(3) 0.0343(2) Uiso 1.000000 R
C11 C -0.777764(3) 0.121130(3) -0.465419(3) 0.02421(17) Uani 1.000000 .
C12 C -0.451543(3) -0.134792(3) -0.167112(3) 0.02632(17) Uani 1.000000 .
H12 H -0.370590(3) -0.198077(3) -0.117699(3) 0.0316(2) Uiso 1.000000 R
C13 C -0.864309(3) 0.032529(3) -0.577692(3) 0.03438(18) Uani 1.000000 .
H13a H -0.822239(4) 0.066336(4) -0.638803(3) 0.0516(3) Uiso 1.000000 GR
H13b H -0.874246(4) -0.126456(3) -0.572453(4) 0.0516(3) Uiso 1.000000 GR
H13c H -0.950697(4) 0.102162(4) -0.592203(4) 0.0516(3) Uiso 1.000000 GR
C14 C -0.654529(3) -0.276458(3) -0.148332(3) 0.02841(17) Uani 1.000000 .
C15 C -0.776904(3) -0.408454(3) -0.146870(3) 0.04210(19) Uani 1.000000 .
H15a H -0.760317(4) -0.502075(4) -0.080423(4) 0.0632(3) Uiso 1.000000 GR
H15b H -0.849408(4) -0.308465(3) -0.145236(4) 0.0632(3) Uiso 1.000000 GR
H15c H -0.799837(4) -0.499871(4) -0.214009(4) 0.0632(3) Uiso 1.000000 GR
C16 C -0.163941(3) 0.043425(3) -0.171680(3) 0.04054(19) Uani 1.000000 .
H16a H -0.172713(3) -0.056536(3) -0.110552(3) 0.0487(2) Uiso 1.000000 R
H16b H -0.137147(3) -0.044999(3) -0.229949(3) 0.0487(2) Uiso 1.000000 R
C17 C -0.056158(3) 0.216980(3) -0.125456(3) 0.0512(2) Uani 1.000000 .
H17a H -0.052769(4) 0.324081(4) -0.183965(4) 0.0768(3) Uiso 1.000000 GR
H17b H -0.076838(4) 0.292049(4) -0.061389(4) 0.0768(3) Uiso 1.000000 GR
H17c H 0.028928(3) 0.143976(3) -0.101937(4) 0.0768(3) Uiso 1.000000 GR
O1 O -0.508925(3) 0.021185(3) -0.100489(3) 0.03143(15) Uani 1.000000 .


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 O0AA 1.5024(3) . ?
S1 N3 1.6657(2) . ?
S1 C11 1.8554(3) . ?
N3 C5 1.4850(2) . ?
O4 C7 1.20691(15) . ?
C5 C9 1.5327(2) . ?
C5 C12 1.5299(2) . ?
C6 C11 1.5213(2) . ?
C7 C14 1.4775(2) . ?
C7 O1 1.3604(2) . ?
C8 C11 1.5179(3) . ?
C9 C16 1.5194(2) . ?
C10 C12 1.4894(2) . ?
C10 C14 1.3233(2) . ?
C11 C13 1.5314(2) . ?
C12 O1 1.44482(18) . ?
C14 C15 1.4899(2) . ?
C16 C17 1.5262(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
N3 S1 O0AA 109.673(3) . . ?
C11 S1 O0AA 104.711(2) . . ?
C11 S1 N3 98.985(2) . . ?
C5 N3 S1 116.413(2) . . ?
C9 C5 N3 108.939(2) . . ?
C12 C5 N3 111.672(3) . . ?
C12 C5 C9 110.939(3) . . ?
C14 C7 O4 128.973(3) . . ?
O1 C7 O4 122.022(3) . . ?
O1 C7 C14 109.004(3) . . ?
C16 C9 C5 113.9947(19) . . ?
C14 C10 C12 110.568(3) . . ?
C6 C11 S1 106.908(2) . . ?
C8 C11 S1 111.868(3) . . ?
C8 C11 C6 112.123(3) . . ?
C13 C11 S1 103.947(3) . . ?
C13 C11 C6 111.050(3) . . ?
C13 C11 C8 110.601(3) . . ?
C10 C12 C5 117.613(3) . . ?
O1 C12 C5 110.497(2) . . ?
O1 C12 C10 104.052(3) . . ?
C10 C14 C7 107.256(3) . . ?
C15 C14 C7 121.094(3) . . ?
C15 C14 C10 131.643(3) . . ?
C17 C16 C9 111.6938(19) . . ?
C12 O1 C7 109.073(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
