# Electronic Supplementary Material (ESI) for ChemComm.
# 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_mo_171124a_0m
_database_code_depnum_ccdc_archive 'CCDC 1588081'
_audit_update_record             
;
2017-12-21 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;
_audit_creation_date             2017-11-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 N O3 S'
_chemical_formula_sum            'C17 H19 N O3 S'
_chemical_formula_weight         317.39
_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'
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'

_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                   5.861(2)
_cell_length_b                   9.841(3)
_cell_length_c                   13.802(5)
_cell_angle_alpha                90.674(5)
_cell_angle_beta                 93.458(5)
_cell_angle_gamma                92.833(5)
_cell_volume                     793.5(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2223
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.09
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5719
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         1.478
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2283
_reflns_number_total             2907
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2907
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0548
_refine_ls_restrained_S_all      1.034
_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)+(0.1009P)²+0.1557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.1703
_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:
 C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 1.3161(6) 0.8254(4) 1.0711(2) 0.0784(9) Uani 1 1 d . . . . .
H1A H 1.2644 0.8561 1.1319 0.118 Uiso 1 1 calc GR . . . .
H1B H 1.4101 0.8962 1.0441 0.118 Uiso 1 1 calc GR . . . .
H1C H 1.4035 0.7463 1.0813 0.118 Uiso 1 1 calc GR . . . .
C2 C 1.1140(4) 0.7904(3) 1.00248(17) 0.0537(6) Uani 1 1 d . . . . .
C3 C 1.0633(5) 0.8693(2) 0.92280(18) 0.0549(6) Uani 1 1 d . . . . .
H3 H 1.1561 0.9463 0.9119 0.066 Uiso 1 1 calc R . . . .
C4 C 0.8789(4) 0.8365(2) 0.85935(17) 0.0500(6) Uani 1 1 d . . . . .
H4 H 0.8452 0.8919 0.8068 0.060 Uiso 1 1 calc R . . . .
C5 C 0.7437(4) 0.7205(2) 0.87438(17) 0.0445(5) Uani 1 1 d . . . . .
C6 C 0.7904(5) 0.6405(2) 0.95410(18) 0.0527(6) Uani 1 1 d . . . . .
H6 H 0.6984 0.5632 0.9650 0.063 Uiso 1 1 calc R . . . .
C7 C 0.9746(5) 0.6768(3) 1.01704(18) 0.0584(7) Uani 1 1 d . . . . .
H7 H 1.0057 0.6233 1.0708 0.070 Uiso 1 1 calc R . . . .
C8 C 0.7750(5) 0.6498(2) 0.64184(17) 0.0518(6) Uani 1 1 d . . . . .
H8 H 0.8580 0.7234 0.6798 0.062 Uiso 1 1 calc R . . . .
C9 C 0.9314(4) 0.5359(3) 0.62595(17) 0.0523(6) Uani 1 1 d . . . . .
H9A H 0.8825 0.4845 0.5673 0.063 Uiso 1 1 calc R . . . .
H9B H 1.0876 0.5711 0.6206 0.063 Uiso 1 1 calc R . . . .
C10 C 0.9134(4) 0.4484(2) 0.71387(16) 0.0447(5) Uani 1 1 d . . . . .
H10 H 1.0124 0.4874 0.7680 0.054 Uiso 1 1 calc R . . . .
C11 C 0.6669(7) 0.7057(3) 0.5497(2) 0.0853(10) Uani 1 1 d . . . . .
H11A H 0.5883 0.6329 0.5123 0.128 Uiso 1 1 calc GR . . . .
H11B H 0.7837 0.7476 0.5125 0.128 Uiso 1 1 calc GR . . . .
H11C H 0.5600 0.7720 0.5656 0.128 Uiso 1 1 calc GR . . . .
C12 C 0.9639(4) 0.3027(2) 0.69748(16) 0.0456(5) Uani 1 1 d . . . . .
C13 C 1.1701(4) 0.2545(3) 0.7317(2) 0.0578(7) Uani 1 1 d . . . . .
H13 H 1.2740 0.3111 0.7687 0.069 Uiso 1 1 calc R . . . .
C14 C 1.2230(5) 0.1229(3) 0.7112(2) 0.0680(8) Uani 1 1 d . . . . .
H14 H 1.3624 0.0911 0.7346 0.082 Uiso 1 1 calc R . . . .
C15 C 1.0724(5) 0.0387(3) 0.6569(2) 0.0681(8) Uani 1 1 d . . . . .
H15 H 1.1093 -0.0500 0.6431 0.082 Uiso 1 1 calc R . . . .
C16 C 0.8674(5) 0.0851(3) 0.6228(2) 0.0700(8) Uani 1 1 d . . . . .
H16 H 0.7645 0.0279 0.5858 0.084 Uiso 1 1 calc R . . . .
C17 C 0.8129(5) 0.2164(3) 0.64321(19) 0.0574(7) Uani 1 1 d . . . . .
H17 H 0.6726 0.2471 0.6201 0.069 Uiso 1 1 calc R . . . .
N1 N 0.5963(3) 0.58328(19) 0.70086(14) 0.0488(5) Uani 1 1 d . . . . .
O1 O 0.3577(3) 0.5865(2) 0.84324(15) 0.0716(6) Uani 1 1 d . . . . .
O2 O 0.4330(3) 0.7938(2) 0.74725(16) 0.0756(6) Uani 1 1 d . . . . .
O3 O 0.6749(3) 0.45561(16) 0.73519(13) 0.0530(5) Uani 1 1 d . . . . .
S1 S 0.51068(10) 0.67480(6) 0.79409(5) 0.0540(3) Uani 1 1 d . . . . .


_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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.495(4) . ?
C2 C3 1.380(4) . ?
C2 C7 1.376(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(3) . ?
C5 C6 1.382(3) . ?
C5 S1 1.743(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.374(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9800 . ?
C8 C9 1.505(4) . ?
C8 C11 1.508(4) . ?
C8 N1 1.496(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.502(3) . ?
C10 H10 0.9800 . ?
C10 C12 1.495(3) . ?
C10 O3 1.451(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.379(3) . ?
C12 C17 1.377(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.364(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.365(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(4) . ?
C17 H17 0.9300 . ?
N1 O3 1.436(2) . ?
N1 S1 1.677(2) . ?
O1 S1 1.425(2) . ?
O2 S1 1.426(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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.4(3) . . ?
C7 C2 C1 120.4(2) . . ?
C7 C2 C3 118.2(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.3(2) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 S1 120.43(19) . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 S1 119.39(18) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.1(2) . . ?
C7 C6 H6 120.4 . . ?
C2 C7 H7 119.2 . . ?
C6 C7 C2 121.7(2) . . ?
C6 C7 H7 119.2 . . ?
C9 C8 H8 109.8 . . ?
C9 C8 C11 114.2(2) . . ?
C11 C8 H8 109.8 . . ?
N1 C8 H8 109.8 . . ?
N1 C8 C9 102.38(18) . . ?
N1 C8 C11 110.5(2) . . ?
C8 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
H9A C9 H9B 108.8 . . ?
C10 C9 C8 104.9(2) . . ?
C10 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
C9 C10 H10 110.1 . . ?
C12 C10 C9 114.4(2) . . ?
C12 C10 H10 110.1 . . ?
O3 C10 C9 103.02(19) . . ?
O3 C10 H10 110.1 . . ?
O3 C10 C12 108.85(17) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C10 120.2(2) . . ?
C17 C12 C10 121.0(2) . . ?
C17 C12 C13 118.6(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.1(3) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.7(2) . . ?
C16 C17 H17 119.6 . . ?
C8 N1 S1 116.55(15) . . ?
O3 N1 C8 108.99(17) . . ?
O3 N1 S1 109.71(14) . . ?
N1 O3 C10 108.09(15) . . ?
N1 S1 C5 110.10(11) . . ?
O1 S1 C5 108.12(12) . . ?
O1 S1 N1 105.89(11) . . ?
O1 S1 O2 121.08(13) . . ?
O2 S1 C5 108.99(12) . . ?
O2 S1 N1 102.21(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 O1 0.98 2.38 3.294(3) 155.3 1_655

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
C1 C2 C3 C4 179.4(2) . . . . ?
C1 C2 C7 C6 -178.6(2) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C3 C2 C7 C6 0.7(4) . . . . ?
C3 C4 C5 C6 1.8(4) . . . . ?
C3 C4 C5 S1 -179.07(18) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C4 C5 S1 N1 86.1(2) . . . . ?
C4 C5 S1 O1 -158.7(2) . . . . ?
C4 C5 S1 O2 -25.3(2) . . . . ?
C5 C6 C7 C2 -0.2(4) . . . . ?
C6 C5 S1 N1 -94.8(2) . . . . ?
C6 C5 S1 O1 20.4(2) . . . . ?
C6 C5 S1 O2 153.8(2) . . . . ?
C7 C2 C3 C4 0.1(4) . . . . ?
C8 C9 C10 C12 154.00(19) . . . . ?
C8 C9 C10 O3 36.0(2) . . . . ?
C8 N1 O3 C10 9.4(2) . . . . ?
C8 N1 S1 C5 -58.40(19) . . . . ?
C8 N1 S1 O1 -175.05(17) . . . . ?
C8 N1 S1 O2 57.31(19) . . . . ?
C9 C8 N1 O3 13.1(2) . . . . ?
C9 C8 N1 S1 137.90(17) . . . . ?
C9 C10 C12 C13 104.1(3) . . . . ?
C9 C10 C12 C17 -71.9(3) . . . . ?
C9 C10 O3 N1 -27.9(2) . . . . ?
C10 C12 C13 C14 -175.7(2) . . . . ?
C10 C12 C17 C16 175.5(2) . . . . ?
C11 C8 C9 C10 -149.3(2) . . . . ?
C11 C8 N1 O3 135.1(2) . . . . ?
C11 C8 N1 S1 -100.1(2) . . . . ?
C12 C10 O3 N1 -149.78(17) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C13 C12 C17 C16 -0.5(4) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C16 C17 C12 0.4(4) . . . . ?
C17 C12 C13 C14 0.3(4) . . . . ?
N1 C8 C9 C10 -29.9(2) . . . . ?
O3 C10 C12 C13 -141.3(2) . . . . ?
O3 C10 C12 C17 42.8(3) . . . . ?
O3 N1 S1 C5 66.04(16) . . . . ?
O3 N1 S1 O1 -50.61(17) . . . . ?
O3 N1 S1 O2 -178.26(13) . . . . ?
S1 C5 C6 C7 179.86(19) . . . . ?
S1 N1 O3 C10 -119.31(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cu_171221D_0m
_database_code_depnum_ccdc_archive 'CCDC 1813075'
_audit_update_record             
;
2017-12-22 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H21 N O4 S'
_chemical_formula_weight         347.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

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

_cell_length_a                   8.13820(10)
_cell_length_b                   11.2235(2)
_cell_length_c                   19.4636(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1777.79(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8970
_cell_measurement_theta_min      4.54
_cell_measurement_theta_max      70.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.798
_shelx_estimated_absorpt_T_min   0.813
_shelx_estimated_absorpt_T_max   0.841
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11341
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.543
_diffrn_reflns_theta_max         70.258
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3168
_reflns_number_gt                3088
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_max     0.901
_reflns_Friedel_fraction_full    0.945

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+0.1714P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0049(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1228 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.034(6)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         3168
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0807
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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_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
C1 C 0.6904(5) 0.3036(4) 0.99149(17) 0.0976(11) Uani 1 1 d . . . . .
H1A H 0.7491 0.2331 0.9782 0.146 Uiso 1 1 calc R U . . .
H1B H 0.5815 0.2822 1.0060 0.146 Uiso 1 1 calc R U . . .
H1C H 0.7471 0.3419 1.0287 0.146 Uiso 1 1 calc R U . . .
C2 C 0.6800(3) 0.3874(2) 0.93127(12) 0.0657(6) Uani 1 1 d . . . . .
C3 C 0.7775(4) 0.4881(3) 0.92812(13) 0.0743(7) Uani 1 1 d . . . . .
H3 H 0.8503 0.5033 0.9639 0.089 Uiso 1 1 calc R U . . .
C4 C 0.7707(3) 0.5662(3) 0.87410(12) 0.0654(6) Uani 1 1 d . . . . .
H4 H 0.8374 0.6335 0.8734 0.078 Uiso 1 1 calc R U . . .
C5 C 0.6626(3) 0.5433(2) 0.82046(11) 0.0535(5) Uani 1 1 d . . . . .
C6 C 0.5644(3) 0.4429(2) 0.82151(12) 0.0596(5) Uani 1 1 d . . . . .
H6 H 0.4930 0.4270 0.7853 0.072 Uiso 1 1 calc R U . . .
C7 C 0.5735(3) 0.3663(2) 0.87699(13) 0.0656(6) Uani 1 1 d . . . . .
H7 H 0.5067 0.2990 0.8779 0.079 Uiso 1 1 calc R U . . .
C8 C 0.9603(3) 0.6040(2) 0.70830(12) 0.0612(6) Uani 1 1 d . . . . .
H8 H 0.9723 0.6145 0.7580 0.073 Uiso 1 1 calc R U . . .
C9 C 1.0118(4) 0.4790(3) 0.6884(2) 0.1007(12) Uani 1 1 d . . . . .
H9A H 1.0751 0.4800 0.6462 0.121 Uiso 1 1 calc R U . . .
H9B H 1.0780 0.4432 0.7244 0.121 Uiso 1 1 calc R U . . .
C10 C 0.8549(3) 0.4109(2) 0.67879(13) 0.0626(6) Uani 1 1 d . . . . .
H10 H 0.8187 0.3791 0.7232 0.075 Uiso 1 1 calc R U . . .
C11 C 1.0556(4) 0.6988(4) 0.67143(17) 0.0973(11) Uani 1 1 d . . . . .
H11A H 1.0545 0.6829 0.6230 0.146 Uiso 1 1 calc R U . . .
H11B H 1.1669 0.6992 0.6877 0.146 Uiso 1 1 calc R U . . .
H11C H 1.0063 0.7751 0.6800 0.146 Uiso 1 1 calc R U . . .
C12 C 0.8522(3) 0.3134(2) 0.62609(11) 0.0556(5) Uani 1 1 d . . . . .
C13 C 0.9244(3) 0.3267(2) 0.56231(14) 0.0677(6) Uani 1 1 d . . . . .
H13 H 0.9799 0.3970 0.5523 0.081 Uiso 1 1 calc R U . . .
C14 C 0.9164(3) 0.2388(3) 0.51312(13) 0.0666(6) Uani 1 1 d . . . . .
H14 H 0.9651 0.2505 0.4704 0.080 Uiso 1 1 calc R U . . .
C15 C 0.8360(3) 0.1335(2) 0.52723(11) 0.0567(5) Uani 1 1 d . . . . .
C16 C 0.7640(3) 0.1182(2) 0.59121(13) 0.0654(6) Uani 1 1 d . . . . .
H16 H 0.7100 0.0474 0.6014 0.078 Uiso 1 1 calc R U . . .
C17 C 0.7720(3) 0.2069(2) 0.63953(12) 0.0603(6) Uani 1 1 d . . . . .
H17 H 0.7227 0.1954 0.6821 0.072 Uiso 1 1 calc R U . . .
C18 C 0.9004(4) 0.0501(4) 0.41760(14) 0.0872(10) Uani 1 1 d . . . . .
H18A H 1.0158 0.0637 0.4243 0.131 Uiso 1 1 calc R U . . .
H18B H 0.8540 0.1156 0.3925 0.131 Uiso 1 1 calc R U . . .
H18C H 0.8850 -0.0223 0.3922 0.131 Uiso 1 1 calc R U . . .
N1 N 0.7817(2) 0.61050(17) 0.68918(10) 0.0560(5) Uani 1 1 d . . . . .
O1 O 0.7043(3) 0.75807(15) 0.77460(10) 0.0778(6) Uani 1 1 d . . . . .
O2 O 0.4888(2) 0.63196(17) 0.72169(10) 0.0708(5) Uani 1 1 d . . . . .
O3 O 0.73984(19) 0.50188(15) 0.65595(8) 0.0568(4) Uani 1 1 d . . . . .
O4 O 0.8212(3) 0.04033(18) 0.48266(9) 0.0747(5) Uani 1 1 d . . . . .
S1 S 0.64812(7) 0.64441(5) 0.75161(3) 0.05742(18) Uani 1 1 d . . . . .


_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
C1 C2 1.505(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.382(4) . ?
C2 C7 1.387(4) . ?
C3 C4 1.370(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 S1 1.760(2) . ?
C6 C7 1.383(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C11 1.500(4) . ?
C8 N1 1.502(3) . ?
C8 C9 1.515(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.500(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O3 1.455(3) . ?
C10 C12 1.501(3) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.381(3) . ?
C12 C17 1.387(3) . ?
C13 C14 1.376(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(4) . ?
C14 H14 0.9300 . ?
C15 O4 1.364(3) . ?
C15 C16 1.387(3) . ?
C16 C17 1.371(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O4 1.425(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 O3 1.422(2) . ?
N1 S1 1.674(2) . ?
O1 S1 1.4272(18) . ?
O2 S1 1.4280(18) . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.7(2) . . ?
C3 C2 C1 120.9(3) . . ?
C7 C2 C1 121.4(3) . . ?
C4 C3 C2 122.3(2) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 S1 119.89(18) . . ?
C4 C5 S1 119.71(19) . . ?
C5 C6 C7 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C2 121.5(2) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
C11 C8 N1 110.3(2) . . ?
C11 C8 C9 113.1(3) . . ?
N1 C8 C9 104.5(2) . . ?
C11 C8 H8 109.6 . . ?
N1 C8 H8 109.6 . . ?
C9 C8 H8 109.6 . . ?
C10 C9 C8 105.5(2) . . ?
C10 C9 H9A 110.6 . . ?
C8 C9 H9A 110.6 . . ?
C10 C9 H9B 110.6 . . ?
C8 C9 H9B 110.6 . . ?
H9A C9 H9B 108.8 . . ?
O3 C10 C9 103.2(2) . . ?
O3 C10 C12 107.09(18) . . ?
C9 C10 C12 118.0(3) . . ?
O3 C10 H10 109.4 . . ?
C9 C10 H10 109.4 . . ?
C12 C10 H10 109.4 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 117.6(2) . . ?
C13 C12 C10 122.0(2) . . ?
C17 C12 C10 120.5(2) . . ?
C14 C13 C12 121.9(2) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
O4 C15 C14 124.9(2) . . ?
O4 C15 C16 116.1(2) . . ?
C14 C15 C16 119.0(2) . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 121.2(2) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 N1 C8 107.65(17) . . ?
O3 N1 S1 111.68(14) . . ?
C8 N1 S1 117.35(15) . . ?
N1 O3 C10 107.96(15) . . ?
C15 O4 C18 117.8(2) . . ?
O1 S1 O2 120.42(12) . . ?
O1 S1 N1 102.86(11) . . ?
O2 S1 N1 105.74(10) . . ?
O1 S1 C5 108.42(11) . . ?
O2 S1 C5 107.96(11) . . ?
N1 S1 C5 111.27(10) . . ?

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
C7 C2 C3 C4 0.5(4) . . . . ?
C1 C2 C3 C4 -179.9(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C3 C4 C5 S1 178.4(2) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
S1 C5 C6 C7 -178.00(18) . . . . ?
C5 C6 C7 C2 -0.6(4) . . . . ?
C3 C2 C7 C6 -0.1(4) . . . . ?
C1 C2 C7 C6 -179.7(3) . . . . ?
C11 C8 C9 C10 -136.0(3) . . . . ?
N1 C8 C9 C10 -16.0(4) . . . . ?
C8 C9 C10 O3 30.1(4) . . . . ?
C8 C9 C10 C12 147.9(2) . . . . ?
O3 C10 C12 C13 73.3(3) . . . . ?
C9 C10 C12 C13 -42.4(4) . . . . ?
O3 C10 C12 C17 -104.8(3) . . . . ?
C9 C10 C12 C17 139.4(3) . . . . ?
C17 C12 C13 C14 0.7(4) . . . . ?
C10 C12 C13 C14 -177.5(2) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
C13 C14 C15 O4 -179.7(2) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
O4 C15 C16 C17 -179.9(2) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C12 -0.3(4) . . . . ?
C13 C12 C17 C16 -0.3(4) . . . . ?
C10 C12 C17 C16 178.0(2) . . . . ?
C11 C8 N1 O3 117.3(2) . . . . ?
C9 C8 N1 O3 -4.5(3) . . . . ?
C11 C8 N1 S1 -115.8(2) . . . . ?
C9 C8 N1 S1 122.4(2) . . . . ?
C8 N1 O3 C10 24.3(2) . . . . ?
S1 N1 O3 C10 -105.87(18) . . . . ?
C9 C10 O3 N1 -33.9(3) . . . . ?
C12 C10 O3 N1 -159.14(18) . . . . ?
C14 C15 O4 C18 2.8(4) . . . . ?
C16 C15 O4 C18 -177.0(2) . . . . ?
O3 N1 S1 O1 -176.11(14) . . . . ?
C8 N1 S1 O1 58.94(19) . . . . ?
O3 N1 S1 O2 -48.96(16) . . . . ?
C8 N1 S1 O2 -173.91(17) . . . . ?
O3 N1 S1 C5 68.00(16) . . . . ?
C8 N1 S1 C5 -56.95(19) . . . . ?
C6 C5 S1 O1 156.17(19) . . . . ?
C4 C5 S1 O1 -22.7(2) . . . . ?
C6 C5 S1 O2 24.2(2) . . . . ?
C4 C5 S1 O2 -154.67(19) . . . . ?
C6 C5 S1 N1 -91.42(19) . . . . ?
C4 C5 S1 N1 89.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C18 H18A O3 0.96 2.51 3.165(3) 125.3 4_556

_refine_diff_density_max         0.133
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.026

