# Electronic Supplementary Material (ESI) for Green 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_SPAO40Twin
_database_code_depnum_ccdc_archive 'CCDC 1552986'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;

_audit_creation_date             2017-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled Mar 28 2017 19:26:29 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H8 Cl2 O2 S'
_chemical_formula_sum            'C9 H8 Cl2 O2 S'
_chemical_formula_weight         251.11
_chemical_absolute_configuration ad
_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'
Cl Cl 0.1484 0.1585 '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'

_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'

_cell_length_a                   7.3712(4)
_cell_length_b                   10.3338(6)
_cell_length_c                   13.8683(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.683(3)
_cell_angle_gamma                90.00
_cell_volume                     1054.20(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.80
_cell_measurement_theta_min      2.77
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0443 before and 0.0368 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0498 before and 0.0377 after correction.
 The Ratio of minimum to maximum transmission is 0.93.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 40912 reflections, Rint = 0.0302
 (31046 with I > 3sig(I), Rint = 0.0268)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4177
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         33.24
_diffrn_reflns_theta_min         1.47
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_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                   'sealed tube'
_diffrn_standards_number         0
_reflns_number_gt                4069
_reflns_number_total             4177
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ApexII
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4177
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0239
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0315P)²+0.1742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0580
_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., Twin
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5011(8)
 0.4989(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17)
3.b X=CH2 refined with riding coordinates:
 C9(H9A,H9B), C18(H18A,H18B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.01130(7) 0.75460(6) 1.04132(4) 0.02242(11) Uani 1 d . . .
Cl2 Cl 0.24282(7) 0.96493(5) 0.98733(4) 0.02084(10) Uani 1 d . . .
S1 S 0.40619(6) 0.71288(5) 1.04400(3) 0.01280(9) Uani 1 d . . .
O1 O 0.3645(2) 0.59941(17) 1.09811(11) 0.0198(3) Uani 1 d . . .
O2 O 0.5741(2) 0.78105(18) 1.06635(11) 0.0200(3) Uani 1 d . . .
C1 C 0.3863(3) 0.6766(2) 0.92075(14) 0.0130(3) Uani 1 d . . .
C2 C 0.2879(3) 0.5668(2) 0.88992(14) 0.0142(3) Uani 1 d . . .
H2 H 0.2278 0.5170 0.9337 0.017 Uiso 1 calc . . R
C3 C 0.2819(3) 0.5337(2) 0.79233(14) 0.0166(4) Uani 1 d . . .
H3 H 0.2173 0.4609 0.7705 0.020 Uiso 1 calc . . R
C4 C 0.3718(3) 0.6088(2) 0.72760(15) 0.0182(4) Uani 1 d . . .
H4 H 0.3670 0.5859 0.6626 0.022 Uiso 1 calc . . R
C5 C 0.4696(3) 0.7185(3) 0.75897(15) 0.0202(4) Uani 1 d . . .
H5 H 0.5293 0.7682 0.7149 0.024 Uiso 1 calc . . R
C6 C 0.4776(3) 0.7533(2) 0.85601(15) 0.0187(4) Uani 1 d . . .
H6 H 0.5423 0.8261 0.8776 0.022 Uiso 1 calc . . R
C7 C 0.2228(3) 0.8315(2) 1.06671(15) 0.0144(3) Uani 1 d . . .
C8 C 0.2550(3) 0.8770(2) 1.16926(16) 0.0202(4) Uani 1 d . . .
H8 H 0.3505 0.9344 1.1826 0.024 Uiso 1 calc . . R
C9 C 0.1588(4) 0.8421(3) 1.24189(17) 0.0293(5) Uani 1 d . . .
H9A H 0.0621 0.7849 1.2315 0.035 Uiso 1 calc . . R
H9B H 0.1875 0.8748 1.3035 0.035 Uiso 1 calc . . R
Cl3 Cl 0.50943(7) 0.24872(6) 0.52691(4) 0.02213(11) Uani 1 d . . .
Cl4 Cl 0.25903(7) 0.03494(6) 0.49619(4) 0.02406(11) Uani 1 d . . .
S2 S 0.11568(6) 0.29443(5) 0.53246(3) 0.01247(8) Uani 1 d . . .
O3 O 0.1598(2) 0.40746(17) 0.59062(11) 0.0198(3) Uani 1 d . . .
O4 O -0.0507(2) 0.22576(17) 0.54551(11) 0.0194(3) Uani 1 d . . .
C10 C 0.1266(3) 0.3354(2) 0.41015(13) 0.0126(3) Uani 1 d . . .
C11 C 0.2113(3) 0.4510(2) 0.38644(14) 0.0148(3) Uani 1 d . . .
H11 H 0.2667 0.5033 0.4343 0.018 Uiso 1 calc . . R
C12 C 0.2108(3) 0.4860(2) 0.28961(15) 0.0179(4) Uani 1 d . . .
H12 H 0.2668 0.5624 0.2723 0.022 Uiso 1 calc . . R
C13 C 0.1274(3) 0.4076(3) 0.21879(15) 0.0192(4) Uani 1 d . . .
H13 H 0.1271 0.4321 0.1542 0.023 Uiso 1 calc . . R
C14 C 0.0438(3) 0.2922(3) 0.24368(15) 0.0210(4) Uani 1 d . . .
H14 H -0.0114 0.2402 0.1956 0.025 Uiso 1 calc . . R
C15 C 0.0424(3) 0.2545(2) 0.33969(14) 0.0174(4) Uani 1 d . . .
H15 H -0.0129 0.1777 0.3568 0.021 Uiso 1 calc . . R
C16 C 0.3036(3) 0.1789(2) 0.56263(14) 0.0143(3) Uani 1 d . . .
C17 C 0.3175(3) 0.1604(3) 0.67033(16) 0.0212(4) Uani 1 d . . .
H17 H 0.3582 0.2302 0.7081 0.025 Uiso 1 calc . . R
C18 C 0.2768(4) 0.0535(3) 0.7153(2) 0.0322(6) Uani 1 d . . .
H18A H 0.2357 -0.0184 0.6800 0.039 Uiso 1 calc . . R
H18B H 0.2891 0.0498 0.7824 0.039 Uiso 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
Cl1 C7 1.765(2) . ?
Cl2 C7 1.776(2) . ?
S1 O1 1.4360(17) . ?
S1 O2 1.4405(17) . ?
S1 C1 1.747(2) . ?
S1 C7 1.867(2) . ?
C1 C2 1.398(3) . ?
C1 C6 1.401(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.394(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.502(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.319(3) . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?
Cl3 C16 1.779(2) . ?
Cl4 C16 1.769(2) . ?
S2 O3 1.4447(17) . ?
S2 O4 1.4383(16) . ?
S2 C10 1.7552(19) . ?
S2 C16 1.856(2) . ?
C10 C11 1.396(3) . ?
C10 C15 1.400(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.396(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.503(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.312(4) . ?
C18 H18A 0.9300 . ?
C18 H18B 0.9300 . ?

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
O1 S1 O2 119.77(10) . . ?
O1 S1 C1 109.20(10) . . ?
O1 S1 C7 105.46(10) . . ?
O2 S1 C1 109.42(10) . . ?
O2 S1 C7 105.31(10) . . ?
C1 S1 C7 106.85(10) . . ?
C2 C1 S1 118.85(16) . . ?
C2 C1 C6 121.56(18) . . ?
C6 C1 S1 119.48(16) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.69(19) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.71(19) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 H6 120.6 . . ?
Cl1 C7 Cl2 109.47(11) . . ?
Cl1 C7 S1 108.08(11) . . ?
Cl2 C7 S1 108.38(10) . . ?
C8 C7 Cl1 114.43(15) . . ?
C8 C7 Cl2 109.24(16) . . ?
C8 C7 S1 107.05(15) . . ?
C7 C8 H8 117.4 . . ?
C9 C8 C7 125.3(2) . . ?
C9 C8 H8 117.4 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
O3 S2 C10 108.77(10) . . ?
O3 S2 C16 104.86(10) . . ?
O4 S2 O3 119.46(10) . . ?
O4 S2 C10 109.46(9) . . ?
O4 S2 C16 106.50(10) . . ?
C10 S2 C16 107.05(9) . . ?
C11 C10 S2 118.88(15) . . ?
C11 C10 C15 122.07(18) . . ?
C15 C10 S2 118.97(16) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.5(2) . . ?
C12 C11 H11 120.8 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.5(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 H15 120.9 . . ?
C14 C15 C10 118.1(2) . . ?
C14 C15 H15 120.9 . . ?
Cl3 C16 S2 108.27(11) . . ?
Cl4 C16 Cl3 109.22(11) . . ?
Cl4 C16 S2 108.22(10) . . ?
C17 C16 Cl3 108.85(15) . . ?
C17 C16 Cl4 114.17(17) . . ?
C17 C16 S2 107.95(15) . . ?
C16 C17 H17 117.4 . . ?
C18 C17 C16 125.2(2) . . ?
C18 C17 H17 117.4 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5011(8)
2 0.4989(8)

####################################################################### 
# 
# 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_SPEC01
_database_code_depnum_ccdc_archive 'CCDC 1552987'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;
_audit_creation_date             2017-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled Mar 28 2017 19:26:29 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 O2 S'
_chemical_formula_sum            'C14 H18 O2 S'
_chemical_formula_weight         250.34
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.8477(5)
_cell_length_b                   7.9550(5)
_cell_length_c                   20.8582(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.801(2)
_cell_angle_gamma                90.00
_cell_volume                     1292.98(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6652
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      2.68
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0540 before and 0.0369 after correction.
The Ratio of minimum to maximum transmission is 0.9494.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.4
_exptl_special_details           
;
Data were corrected for decay and absorption using the program SADABS
 based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995).
;
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11046
_diffrn_reflns_theta_full        26.73
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         2.68
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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                   'sealed tube'
_diffrn_standards_number         0
_reflns_number_gt                2510
_reflns_number_total             2733
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Apex II'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2733
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+0.5438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0755
_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.'
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.30487(4) 0.55696(4) 0.652653(14) 0.01798(10) Uani 1 d . . .
O1 O 0.66271(10) 0.73973(11) 0.54645(4) 0.01727(19) Uani 1 d . . .
H1 H 0.6031 0.7344 0.5103 0.026 Uiso 1 calc . . GR
C1 C 0.45619(14) 0.57313(14) 0.59227(5) 0.0135(2) Uani 1 d . . .
H1A H 0.3912 0.5618 0.5483 0.016 Uiso 1 calc . . R
O2 O 0.57151(11) 0.30626(11) 0.56794(4) 0.01966(19) Uani 1 d . . .
C2 C 0.55205(14) 0.74417(14) 0.59649(5) 0.0145(2) Uani 1 d . . .
C3 C 0.67226(14) 0.75660(14) 0.65955(5) 0.0149(2) Uani 1 d . . .
H3A H 0.6036 0.7512 0.6964 0.018 Uiso 1 calc . . R
H3B H 0.7314 0.8667 0.6613 0.018 Uiso 1 calc . . R
C4 C 0.80644(14) 0.61630(15) 0.66641(5) 0.0146(2) Uani 1 d . . .
H4 H 0.8798 0.6277 0.6306 0.017 Uiso 1 calc . . R
C5 C 0.71831(15) 0.44379(14) 0.66046(6) 0.0168(2) Uani 1 d . . .
H5A H 0.8065 0.3563 0.6571 0.020 Uiso 1 calc . . R
H5B H 0.6649 0.4217 0.7003 0.020 Uiso 1 calc . . R
C6 C 0.58264(14) 0.42908(14) 0.60310(5) 0.0142(2) Uani 1 d . . .
C7 C 0.43000(16) 0.89309(16) 0.58694(6) 0.0215(3) Uani 1 d . . .
H7A H 0.4963 0.9974 0.5868 0.032 Uiso 1 calc . . GR
H7B H 0.3579 0.8964 0.6222 0.032 Uiso 1 calc . . GR
H7C H 0.3571 0.8813 0.5457 0.032 Uiso 1 calc . . GR
C8 C 0.92181(15) 0.62820(16) 0.73054(6) 0.0190(3) Uani 1 d . . .
H8A H 0.8517 0.6189 0.7663 0.029 Uiso 1 calc . . GR
H8B H 0.9817 0.7365 0.7331 0.029 Uiso 1 calc . . GR
H8C H 1.0061 0.5368 0.7334 0.029 Uiso 1 calc . . GR
C9 C 0.18731(14) 0.37230(15) 0.62754(5) 0.0148(2) Uani 1 d . . .
C10 C 0.16486(15) 0.24950(16) 0.67321(6) 0.0198(3) Uani 1 d . . .
H10 H 0.2191 0.2611 0.7162 0.024 Uiso 1 calc . . R
C11 C 0.06309(16) 0.10960(17) 0.65607(7) 0.0262(3) Uani 1 d . . .
H11 H 0.0467 0.0268 0.6876 0.031 Uiso 1 calc . . R
C12 C -0.01435(17) 0.09034(17) 0.59334(7) 0.0284(3) Uani 1 d . . .
H12 H -0.0835 -0.0054 0.5817 0.034 Uiso 1 calc . . R
C13 C 0.00985(17) 0.21184(19) 0.54773(6) 0.0274(3) Uani 1 d . . .
H13 H -0.0416 0.1981 0.5045 0.033 Uiso 1 calc . . R
C14 C 0.10842(15) 0.35350(17) 0.56447(6) 0.0204(3) Uani 1 d . . .
H14 H 0.1221 0.4374 0.5331 0.024 Uiso 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 C1 1.8350(11) . ?
S1 C9 1.7802(12) . ?
O1 H1 0.8400 . ?
O1 C2 1.4350(13) . ?
C1 H1A 1.0000 . ?
C1 C2 1.5522(15) . ?
C1 C6 1.5152(15) . ?
O2 C6 1.2186(14) . ?
C2 C3 1.5284(15) . ?
C2 C7 1.5216(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5295(16) . ?
C4 H4 1.0000 . ?
C4 C5 1.5351(16) . ?
C4 C8 1.5269(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5090(15) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.3902(17) . ?
C9 C14 1.3940(16) . ?
C10 H10 0.9500 . ?
C10 C11 1.3916(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.3879(18) . ?
C14 H14 0.9500 . ?

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
C9 S1 C1 102.17(5) . . ?
C2 O1 H1 109.5 . . ?
S1 C1 H1A 108.8 . . ?
C2 C1 S1 111.80(8) . . ?
C2 C1 H1A 108.8 . . ?
C6 C1 S1 108.08(8) . . ?
C6 C1 H1A 108.8 . . ?
C6 C1 C2 110.49(9) . . ?
O1 C2 C1 105.56(9) . . ?
O1 C2 C3 105.22(9) . . ?
O1 C2 C7 110.48(9) . . ?
C3 C2 C1 110.55(9) . . ?
C7 C2 C1 112.44(9) . . ?
C7 C2 C3 112.15(9) . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C2 C3 C4 112.41(9) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C3 C4 H4 108.3 . . ?
C3 C4 C5 110.25(9) . . ?
C5 C4 H4 108.3 . . ?
C8 C4 C3 111.53(9) . . ?
C8 C4 H4 108.3 . . ?
C8 C4 C5 109.93(10) . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 C4 113.72(9) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
O2 C6 C1 121.18(10) . . ?
O2 C6 C5 122.20(10) . . ?
C5 C6 C1 116.59(9) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 S1 118.78(9) . . ?
C10 C9 C14 119.55(11) . . ?
C14 C9 S1 121.54(9) . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.09(12) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.38(12) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.44(12) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.77(12) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.77(12) . . ?
C13 C14 H14 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
