# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_compound3ba
_database_code_depnum_ccdc_archive 'CCDC 1544460'
_audit_update_record             
;
2017-04-17 deposited with the CCDC.
2019-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H24 S'
_chemical_formula_weight         260.42

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   10.7279(4)
_cell_length_b                   9.5705(3)
_cell_length_c                   14.6231(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.351(3)
_cell_angle_gamma                90.00
_cell_volume                     1494.83(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2324
_cell_measurement_theta_min      3.8150
_cell_measurement_theta_max      27.4330

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9055
_exptl_absorpt_correction_T_max  0.9632
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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       'ω scans'
_diffrn_detector_area_resol_mean 16.3990
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11755
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0629
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         28.04
_reflns_number_total             3225
_reflns_number_gt                2268
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_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)+(0.0456P)²+0.6036P] 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_number_reflns         3225
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.09748(5) 0.13750(6) 0.15700(4) 0.02872(18) Uani 1 1 d . . .
C1 C 0.19060(19) 0.1311(2) 0.33590(14) 0.0250(5) Uani 1 1 d . . .
C2 C 0.2902(2) 0.1808(3) 0.39492(15) 0.0335(6) Uani 1 1 d . . .
H2A H 0.3192 0.2735 0.3871 0.040 Uiso 1 1 calc R . .
C3 C 0.3479(2) 0.0993(3) 0.46446(16) 0.0382(6) Uani 1 1 d . . .
H3A H 0.4163 0.1351 0.5035 0.046 Uiso 1 1 calc R . .
C4 C 0.3049(2) -0.0353(3) 0.47643(16) 0.0389(6) Uani 1 1 d . . .
H4A H 0.3416 -0.0913 0.5254 0.047 Uiso 1 1 calc R . .
C5 C 0.2084(2) -0.0880(2) 0.41714(15) 0.0329(5) Uani 1 1 d . . .
H5A H 0.1808 -0.1809 0.4257 0.039 Uiso 1 1 calc R . .
C6 C 0.1499(2) -0.0084(2) 0.34460(14) 0.0259(5) Uani 1 1 d . . .
C7 C 0.1275(2) 0.2300(2) 0.26545(14) 0.0258(5) Uani 1 1 d . . .
H7A H 0.1924 0.3015 0.2545 0.031 Uiso 1 1 calc R . .
C8 C 0.0303(2) -0.0200(2) 0.19209(15) 0.0258(5) Uani 1 1 d . . .
C9 C 0.0544(2) -0.0728(2) 0.27745(15) 0.0261(5) Uani 1 1 d . . .
C10 C -0.0529(2) -0.0831(2) 0.11319(15) 0.0310(5) Uani 1 1 d . . .
H10A H -0.0721 -0.1810 0.1288 0.037 Uiso 1 1 calc R . .
H10B H -0.0063 -0.0850 0.0579 0.037 Uiso 1 1 calc R . .
C11 C -0.1760(2) -0.0045(3) 0.09028(17) 0.0389(6) Uani 1 1 d . . .
H11A H -0.2245 -0.0504 0.0386 0.058 Uiso 1 1 calc R . .
H11B H -0.1581 0.0921 0.0736 0.058 Uiso 1 1 calc R . .
H11C H -0.2243 -0.0049 0.1439 0.058 Uiso 1 1 calc R . .
C12 C -0.0122(2) -0.2024(2) 0.30752(16) 0.0364(6) Uani 1 1 d . . .
H12A H 0.0511 -0.2721 0.3310 0.044 Uiso 1 1 calc R . .
H12B H -0.0613 -0.2437 0.2535 0.044 Uiso 1 1 calc R . .
C13 C -0.0993(2) -0.1729(3) 0.38155(18) 0.0469(7) Uani 1 1 d . . .
H13A H -0.1382 -0.2603 0.3991 0.070 Uiso 1 1 calc R . .
H13B H -0.1645 -0.1071 0.3579 0.070 Uiso 1 1 calc R . .
H13C H -0.0512 -0.1323 0.4354 0.070 Uiso 1 1 calc R . .
C14 C 0.0147(2) 0.3145(2) 0.29704(15) 0.0288(5) Uani 1 1 d . . .
C15 C 0.0620(2) 0.4016(2) 0.38155(16) 0.0392(6) Uani 1 1 d . . .
H15A H -0.0064 0.4597 0.4003 0.059 Uiso 1 1 calc R . .
H15B H 0.1310 0.4616 0.3662 0.059 Uiso 1 1 calc R . .
H15C H 0.0915 0.3390 0.4320 0.059 Uiso 1 1 calc R . .
C16 C -0.0927(2) 0.2211(2) 0.32270(18) 0.0371(6) Uani 1 1 d . . .
H16A H -0.1589 0.2792 0.3448 0.056 Uiso 1 1 calc R . .
H16B H -0.0614 0.1559 0.3712 0.056 Uiso 1 1 calc R . .
H16C H -0.1266 0.1683 0.2685 0.056 Uiso 1 1 calc R . .
C17 C -0.0342(2) 0.4151(2) 0.22037(16) 0.0380(6) Uani 1 1 d . . .
H17A H -0.0991 0.4751 0.2424 0.057 Uiso 1 1 calc R . .
H17B H -0.0696 0.3614 0.1671 0.057 Uiso 1 1 calc R . .
H17C H 0.0349 0.4731 0.2027 0.057 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 C8 1.767(2) . ?
S1 C7 1.818(2) . ?
C1 C2 1.393(3) . ?
C1 C6 1.414(3) . ?
C1 C7 1.512(3) . ?
C2 C3 1.382(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.385(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.405(3) . ?
C5 H5A 0.9500 . ?
C6 C9 1.485(3) . ?
C7 C14 1.561(3) . ?
C7 H7A 1.0000 . ?
C8 C9 1.349(3) . ?
C8 C10 1.517(3) . ?
C9 C12 1.516(3) . ?
C10 C11 1.530(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.521(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C16 1.533(3) . ?
C14 C17 1.533(3) . ?
C14 C15 1.537(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C8 S1 C7 101.86(10) . . ?
C2 C1 C6 119.5(2) . . ?
C2 C1 C7 118.52(19) . . ?
C6 C1 C7 121.99(19) . . ?
C3 C2 C1 121.9(2) . . ?
C3 C2 H2A 119.0 . . ?
C1 C2 H2A 119.0 . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 122.1(2) . . ?
C4 C5 H5A 118.9 . . ?
C6 C5 H5A 118.9 . . ?
C5 C6 C1 117.3(2) . . ?
C5 C6 C9 120.4(2) . . ?
C1 C6 C9 122.14(19) . . ?
C1 C7 C14 115.66(17) . . ?
C1 C7 S1 108.74(14) . . ?
C14 C7 S1 115.56(15) . . ?
C1 C7 H7A 105.3 . . ?
C14 C7 H7A 105.3 . . ?
S1 C7 H7A 105.3 . . ?
C9 C8 C10 127.0(2) . . ?
C9 C8 S1 122.69(17) . . ?
C10 C8 S1 110.25(15) . . ?
C8 C9 C6 121.13(19) . . ?
C8 C9 C12 121.3(2) . . ?
C6 C9 C12 117.52(19) . . ?
C8 C10 C11 113.91(19) . . ?
C8 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C8 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 C13 113.07(19) . . ?
C9 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C9 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
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 . . ?
C16 C14 C17 109.4(2) . . ?
C16 C14 C15 108.60(18) . . ?
C17 C14 C15 108.18(18) . . ?
C16 C14 C7 113.06(17) . . ?
C17 C14 C7 109.32(18) . . ?
C15 C14 C7 108.19(18) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C6 C1 C2 C3 -2.5(3) . . . . ?
C7 C1 C2 C3 176.2(2) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 2.3(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C1 -2.1(3) . . . . ?
C4 C5 C6 C9 174.5(2) . . . . ?
C2 C1 C6 C5 3.7(3) . . . . ?
C7 C1 C6 C5 -174.92(19) . . . . ?
C2 C1 C6 C9 -172.83(19) . . . . ?
C7 C1 C6 C9 8.5(3) . . . . ?
C2 C1 C7 C14 -90.3(2) . . . . ?
C6 C1 C7 C14 88.4(2) . . . . ?
C2 C1 C7 S1 137.79(17) . . . . ?
C6 C1 C7 S1 -43.5(2) . . . . ?
C8 S1 C7 C1 47.28(16) . . . . ?
C8 S1 C7 C14 -84.72(17) . . . . ?
C7 S1 C8 C9 -26.3(2) . . . . ?
C7 S1 C8 C10 154.65(15) . . . . ?
C10 C8 C9 C6 172.5(2) . . . . ?
S1 C8 C9 C6 -6.4(3) . . . . ?
C10 C8 C9 C12 -5.7(3) . . . . ?
S1 C8 C9 C12 175.39(16) . . . . ?
C5 C6 C9 C8 -155.8(2) . . . . ?
C1 C6 C9 C8 20.7(3) . . . . ?
C5 C6 C9 C12 22.5(3) . . . . ?
C1 C6 C9 C12 -161.00(19) . . . . ?
C9 C8 C10 C11 108.4(3) . . . . ?
S1 C8 C10 C11 -72.6(2) . . . . ?
C8 C9 C12 C13 -113.0(2) . . . . ?
C6 C9 C12 C13 68.6(3) . . . . ?
C1 C7 C14 C16 -61.0(2) . . . . ?
S1 C7 C14 C16 67.7(2) . . . . ?
C1 C7 C14 C17 176.92(18) . . . . ?
S1 C7 C14 C17 -54.4(2) . . . . ?
C1 C7 C14 C15 59.3(2) . . . . ?
S1 C7 C14 C15 -172.00(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.8918
_diffrn_reflns_theta_full        24.9737
_diffrn_measured_fraction_theta_full 0.9968
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.055


