# Electronic Supplementary Material (ESI) for Polymer 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_thiol-lactide
_database_code_depnum_ccdc_archive 'CCDC 1586334'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;
_audit_creation_date             2016-07-21
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2016.07.08 svn.r3311 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 O6 S2'
_chemical_formula_sum            'C22 H24 O6 S2'
_chemical_formula_weight         448.53
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5834(9)
_cell_length_b                   7.3620(11)
_cell_length_c                   12.537(2)
_cell_angle_alpha                91.1515(18)
_cell_angle_beta                 93.4047(17)
_cell_angle_gamma                100.6667(17)
_cell_volume                     505.29(14)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5170
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.817
_shelx_estimated_absorpt_T_max   0.849
_shelx_estimated_absorpt_T_min   0.826
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0731 before and 0.0389 after correction.
The Ratio of minimum to maximum transmission is 0.9224.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             236
_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.658
_exptl_crystal_size_mid          0.566
_exptl_crystal_size_min          0.559
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8401
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.573
_diffrn_reflns_theta_min         1.628
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           35
_diffrn_source_voltage           45
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2568
_reflns_number_total             2818
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2015)'
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2818
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0393P)²+0.3110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0871
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C7(H7), C6(H6)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.34478(5) 0.15406(4) 0.20403(2) 0.01422(9) Uani 1 1 d . . . . .
O2 O 0.47609(16) -0.16021(11) 0.06287(6) 0.01243(17) Uani 1 1 d . . . . .
O1 O 0.10934(16) -0.26105(13) -0.01398(7) 0.01682(19) Uani 1 1 d . . . . .
O3 O 1.18274(17) 0.82994(13) 0.42835(7) 0.0191(2) Uani 1 1 d . . . . .
C5 C 0.6133(2) 0.51429(15) 0.23632(9) 0.0112(2) Uani 1 1 d . . . . .
C1 C 0.2927(2) -0.14495(16) -0.00811(9) 0.0112(2) Uani 1 1 d . . . . .
C2 C 0.6724(2) -0.00659(15) 0.08863(9) 0.0106(2) Uani 1 1 d . . . . .
H2 H 0.8272 -0.0564 0.0958 0.013 Uiso 1 1 calc R . . . .
C10 C 0.8398(2) 0.58573(16) 0.19742(9) 0.0117(2) Uani 1 1 d . . . . .
H10 H 0.8682 0.5608 0.1251 0.014 Uiso 1 1 calc R . . . .
C9 C 1.0244(2) 0.69267(16) 0.26301(9) 0.0131(2) Uani 1 1 d . . . . .
H9 H 1.1767 0.7414 0.2351 0.016 Uiso 1 1 calc R . . . .
C3 C 0.6321(2) 0.07427(16) 0.19824(9) 0.0116(2) Uani 1 1 d . . . . .
H3A H 0.7673 0.1792 0.2175 0.014 Uiso 1 1 calc R . . . .
H3B H 0.6385 -0.0213 0.2523 0.014 Uiso 1 1 calc R . . . .
C7 C 0.7588(2) 0.66372(17) 0.40895(9) 0.0147(2) Uani 1 1 d . . . . .
H7 H 0.7291 0.6918 0.4807 0.018 Uiso 1 1 calc R . . . .
C6 C 0.5751(2) 0.55742(17) 0.34200(9) 0.0136(2) Uani 1 1 d . . . . .
H6 H 0.4203 0.5133 0.3690 0.016 Uiso 1 1 calc R . . . .
C8 C 0.9868(2) 0.72867(16) 0.36961(9) 0.0132(2) Uani 1 1 d . . . . .
C4 C 0.4190(2) 0.39479(16) 0.16433(10) 0.0131(2) Uani 1 1 d . . . . .
H4A H 0.4740 0.3973 0.0907 0.016 Uiso 1 1 calc R . . . .
H4B H 0.2687 0.4483 0.1633 0.016 Uiso 1 1 calc R . . . .
C11 C 1.1752(3) 0.8296(2) 0.54218(11) 0.0233(3) Uani 1 1 d . . . . .
H11A H 1.0472 0.8948 0.5638 0.035 Uiso 1 1 calc GR . . . .
H11B H 1.3335 0.8921 0.5751 0.035 Uiso 1 1 calc GR . . . .
H11C H 1.1400 0.7018 0.5656 0.035 Uiso 1 1 calc GR . . . .


_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 C3 1.8122(12) . ?
S1 C4 1.8299(12) . ?
O2 C1 1.3383(14) . ?
O2 C2 1.4383(14) . ?
O1 C1 1.2037(14) . ?
O3 C8 1.3696(15) . ?
O3 C11 1.4303(16) . ?
C5 C10 1.3972(16) . ?
C5 C6 1.3940(15) . ?
C5 C4 1.5047(16) . ?
C1 C2 1.5133(16) 2_655 ?
C2 C1 1.5133(16) 2_655 ?
C2 H2 1.0000 . ?
C2 C3 1.5319(15) . ?
C10 H10 0.9500 . ?
C10 C9 1.3894(16) . ?
C9 H9 0.9500 . ?
C9 C8 1.3929(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C7 H7 0.9500 . ?
C7 C6 1.3937(17) . ?
C7 C8 1.3969(17) . ?
C6 H6 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
C3 S1 C4 103.53(5) . . ?
C1 O2 C2 121.08(9) . . ?
C8 O3 C11 117.27(11) . . ?
C10 C5 C4 119.84(10) . . ?
C6 C5 C10 118.15(11) . . ?
C6 C5 C4 122.01(10) . . ?
O2 C1 C2 119.68(10) . 2_655 ?
O1 C1 O2 119.91(11) . . ?
O1 C1 C2 120.07(10) . 2_655 ?
O2 C2 C1 116.16(9) . 2_655 ?
O2 C2 H2 107.5 . . ?
O2 C2 C3 107.88(9) . . ?
C1 C2 H2 107.5 2_655 . ?
C1 C2 C3 109.92(9) 2_655 . ?
C3 C2 H2 107.5 . . ?
C5 C10 H10 119.5 . . ?
C9 C10 C5 120.96(10) . . ?
C9 C10 H10 119.5 . . ?
C10 C9 H9 119.9 . . ?
C10 C9 C8 120.23(11) . . ?
C8 C9 H9 119.9 . . ?
S1 C3 H3A 108.8 . . ?
S1 C3 H3B 108.8 . . ?
C2 C3 S1 113.94(8) . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.43(10) . . ?
C8 C7 H7 120.3 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.55(11) . . ?
C7 C6 H6 119.2 . . ?
O3 C8 C9 115.66(11) . . ?
O3 C8 C7 124.75(11) . . ?
C9 C8 C7 119.59(11) . . ?
S1 C4 H4A 108.7 . . ?
S1 C4 H4B 108.7 . . ?
C5 C4 S1 114.06(8) . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
O2 C2 C3 S1 -59.29(10) . . . . ?
C5 C10 C9 C8 0.75(17) . . . . ?
C1 O2 C2 C1 -19.89(15) . . . 2_655 ?
C1 O2 C2 C3 103.99(11) . . . . ?
C1 C2 C3 S1 68.28(11) 2_655 . . . ?
C2 O2 C1 O1 -166.06(10) . . . . ?
C2 O2 C1 C2 20.57(16) . . . 2_655 ?
C10 C5 C6 C7 -2.04(17) . . . . ?
C10 C5 C4 S1 113.17(11) . . . . ?
C10 C9 C8 O3 177.81(10) . . . . ?
C10 C9 C8 C7 -2.90(17) . . . . ?
C3 S1 C4 C5 -60.13(9) . . . . ?
C6 C5 C10 C9 1.70(17) . . . . ?
C6 C5 C4 S1 -66.94(13) . . . . ?
C6 C7 C8 O3 -178.22(11) . . . . ?
C6 C7 C8 C9 2.56(17) . . . . ?
C8 C7 C6 C5 -0.08(18) . . . . ?
C4 S1 C3 C2 -89.00(9) . . . . ?
C4 C5 C10 C9 -178.41(10) . . . . ?
C4 C5 C6 C7 178.08(11) . . . . ?
C11 O3 C8 C9 -164.19(11) . . . . ?
C11 O3 C8 C7 16.56(17) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id thiol-lactide
_olex2_submission_special_instructions 'No special instructions were received'
