# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo_170508aa
_database_code_depnum_ccdc_archive 'CCDC 1548828'
_audit_update_record             
;
2017-05-09 deposited with the CCDC.
2017-09-22 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 H17 N O3 S'
_chemical_formula_weight         327.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.5580(12)
_cell_length_b                   9.3310(6)
_cell_length_c                   9.8891(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.367(2)
_cell_angle_gamma                90
_cell_volume                     1619.71(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9852
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      27.40

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   0.6791
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.214
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31427
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.002
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3719
_reflns_number_gt                2888
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX3'
_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)+(0.0614P)²+0.7110P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3719
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1158
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_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
S1 S 0.65246(2) 0.34747(5) 0.43346(5) 0.03471(15) Uani 1 1 d . . . . .
C1 C 0.83833(11) 0.5349(2) 0.62499(17) 0.0344(4) Uani 1 1 d . . . . .
O1 O 0.85517(9) 0.21291(17) 0.69956(13) 0.0505(4) Uani 1 1 d . . . . .
N1 N 0.82845(8) 0.30890(17) 0.49522(14) 0.0327(4) Uani 1 1 d . . . . .
H1 H 0.8332 0.3007 0.4092 0.039 Uiso 1 1 calc R U . . .
O2 O 0.69127(8) 0.22640(14) 0.37777(15) 0.0463(4) Uani 1 1 d . . . . .
C2 C 0.91740(12) 0.5346(2) 0.6175(2) 0.0471(5) Uani 1 1 d . . . . .
H2 H 0.9414 0.4662 0.5650 0.057 Uiso 1 1 calc R U . . .
O3 O 0.58950(8) 0.32299(17) 0.52063(15) 0.0499(4) Uani 1 1 d . . . . .
C3 C 0.96036(15) 0.6354(3) 0.6877(3) 0.0646(7) Uani 1 1 d . . . . .
H3 H 1.0132 0.6350 0.6819 0.078 Uiso 1 1 calc R U . . .
C6 C 0.80230(13) 0.6374(2) 0.70515(19) 0.0430(5) Uani 1 1 d . . . . .
C5 C 0.84683(16) 0.7376(3) 0.7742(3) 0.0639(7) Uani 1 1 d . . . . .
H5 H 0.8236 0.8067 0.8270 0.077 Uiso 1 1 calc R U . . .
C4 C 0.92534(17) 0.7361(3) 0.7656(3) 0.0750(8) Uani 1 1 d . . . . .
H4 H 0.9544 0.8035 0.8129 0.090 Uiso 1 1 calc R U . . .
C8 C 0.68164(12) 0.5953(2) 0.5766(2) 0.0451(5) Uani 1 1 d . . . . .
H8A H 0.6272 0.5820 0.5851 0.054 Uiso 1 1 calc R U . . .
H8B H 0.6898 0.6737 0.5142 0.054 Uiso 1 1 calc R U . . .
C7 C 0.71725(13) 0.6316(2) 0.7138(2) 0.0498(5) Uani 1 1 d . . . . .
H7A H 0.6983 0.7236 0.7441 0.060 Uiso 1 1 calc R U . . .
H7B H 0.7030 0.5596 0.7793 0.060 Uiso 1 1 calc R U . . .
C9 C 0.71703(10) 0.45995(19) 0.52266(17) 0.0323(4) Uani 1 1 d . . . . .
C10 C 0.79103(10) 0.43110(19) 0.54678(16) 0.0292(4) Uani 1 1 d . . . . .
C11 C 0.85691(10) 0.2048(2) 0.57692(18) 0.0346(4) Uani 1 1 d . . . . .
C12 C 0.89050(15) 0.0790(3) 0.5046(2) 0.0626(7) Uani 1 1 d . . . . .
H12A H 0.8822 0.0901 0.4089 0.094 Uiso 1 1 calc R U . . .
H12B H 0.8666 -0.0076 0.5342 0.094 Uiso 1 1 calc R U . . .
H12C H 0.9442 0.0743 0.5246 0.094 Uiso 1 1 calc R U . . .
C13 C 0.61893(10) 0.4560(2) 0.29837(19) 0.0354(4) Uani 1 1 d . . . . .
C14 C 0.65746(13) 0.4588(2) 0.1799(2) 0.0478(5) Uani 1 1 d . . . . .
H14 H 0.7029 0.4088 0.1712 0.057 Uiso 1 1 calc R U . . .
C15 C 0.62676(17) 0.5386(3) 0.0725(2) 0.0617(7) Uani 1 1 d . . . . .
H15 H 0.6516 0.5404 -0.0095 0.074 Uiso 1 1 calc R U . . .
C16 C 0.56078(15) 0.6140(2) 0.0860(3) 0.0595(7) Uani 1 1 d . . . . .
H16 H 0.5412 0.6669 0.0134 0.071 Uiso 1 1 calc R U . . .
C17 C 0.52348(14) 0.6125(3) 0.2049(3) 0.0656(7) Uani 1 1 d . . . . .
H17 H 0.4789 0.6653 0.2139 0.079 Uiso 1 1 calc R U . . .
C18 C 0.55175(12) 0.5327(3) 0.3119(2) 0.0548(6) Uani 1 1 d . . . . .
H18 H 0.5260 0.5302 0.3930 0.066 Uiso 1 1 calc R U . . .


_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 O2 1.4359(14) . ?
S1 O3 1.4363(15) . ?
S1 C9 1.7656(18) . ?
S1 C13 1.7664(19) . ?
C1 C2 1.392(3) . ?
C1 C6 1.403(3) . ?
C1 C10 1.481(2) . ?
O1 C11 1.216(2) . ?
N1 C11 1.352(2) . ?
N1 C10 1.417(2) . ?
N1 H1 0.8600 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(4) . ?
C3 H3 0.9300 . ?
C6 C5 1.388(3) . ?
C6 C7 1.499(3) . ?
C5 C4 1.383(4) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C8 C9 1.511(3) . ?
C8 C7 1.518(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.343(2) . ?
C11 C12 1.502(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.367(3) . ?
C13 C18 1.389(3) . ?
C14 C15 1.395(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.365(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.359(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(3) . ?
C17 H17 0.9300 . ?
C18 H18 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
O2 S1 O3 118.96(9) . . ?
O2 S1 C9 110.76(8) . . ?
O3 S1 C9 106.79(9) . . ?
O2 S1 C13 108.29(9) . . ?
O3 S1 C13 107.32(9) . . ?
C9 S1 C13 103.62(8) . . ?
C2 C1 C6 119.68(18) . . ?
C2 C1 C10 121.22(18) . . ?
C6 C1 C10 119.08(17) . . ?
C11 N1 C10 122.09(14) . . ?
C11 N1 H1 119.0 . . ?
C10 N1 H1 119.0 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 123.1(2) . . ?
C1 C6 C7 118.12(18) . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C9 C8 C7 109.75(16) . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C6 C7 C8 110.27(17) . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C10 C9 C8 120.62(16) . . ?
C10 C9 S1 125.22(14) . . ?
C8 C9 S1 114.13(13) . . ?
C9 C10 N1 123.53(16) . . ?
C9 C10 C1 119.33(16) . . ?
N1 C10 C1 117.06(15) . . ?
O1 C11 N1 122.24(17) . . ?
O1 C11 C12 122.88(18) . . ?
N1 C11 C12 114.88(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 120.81(19) . . ?
C14 C13 S1 119.73(16) . . ?
C18 C13 S1 119.40(16) . . ?
C13 C14 C15 118.2(2) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.9(2) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 119.7(2) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?

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 -0.5(3) . . . . ?
C10 C1 C2 C3 177.79(19) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C10 C1 C6 C5 -177.66(18) . . . . ?
C2 C1 C6 C7 -178.29(19) . . . . ?
C10 C1 C6 C7 3.4(3) . . . . ?
C1 C6 C5 C4 -0.6(4) . . . . ?
C7 C6 C5 C4 178.3(2) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C6 C5 C4 C3 0.4(4) . . . . ?
C5 C6 C7 C8 141.6(2) . . . . ?
C1 C6 C7 C8 -39.5(3) . . . . ?
C9 C8 C7 C6 53.4(2) . . . . ?
C7 C8 C9 C10 -35.2(3) . . . . ?
C7 C8 C9 S1 143.07(16) . . . . ?
O2 S1 C9 C10 -5.78(19) . . . . ?
O3 S1 C9 C10 125.15(17) . . . . ?
C13 S1 C9 C10 -121.70(17) . . . . ?
O2 S1 C9 C8 176.09(14) . . . . ?
O3 S1 C9 C8 -52.97(16) . . . . ?
C13 S1 C9 C8 60.18(16) . . . . ?
C8 C9 C10 N1 -177.66(16) . . . . ?
S1 C9 C10 N1 4.3(3) . . . . ?
C8 C9 C10 C1 -1.1(3) . . . . ?
S1 C9 C10 C1 -179.14(13) . . . . ?
C11 N1 C10 C9 -115.1(2) . . . . ?
C11 N1 C10 C1 68.3(2) . . . . ?
C2 C1 C10 C9 -159.66(18) . . . . ?
C6 C1 C10 C9 18.7(3) . . . . ?
C2 C1 C10 N1 17.1(2) . . . . ?
C6 C1 C10 N1 -164.58(16) . . . . ?
C10 N1 C11 O1 -3.4(3) . . . . ?
C10 N1 C11 C12 176.50(18) . . . . ?
O2 S1 C13 C14 -29.33(18) . . . . ?
O3 S1 C13 C14 -158.91(16) . . . . ?
C9 S1 C13 C14 88.32(17) . . . . ?
O2 S1 C13 C18 147.84(17) . . . . ?
O3 S1 C13 C18 18.3(2) . . . . ?
C9 S1 C13 C18 -94.51(18) . . . . ?
C18 C13 C14 C15 -1.1(3) . . . . ?
S1 C13 C14 C15 176.02(16) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C15 C16 C17 C18 -0.9(4) . . . . ?
C16 C17 C18 C13 1.0(4) . . . . ?
C14 C13 C18 C17 0.0(3) . . . . ?
S1 C13 C18 C17 -177.10(19) . . . . ?

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
N1 H1 O1 0.86 2.12 2.9791(19) 174.8 4_565

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.058



####################################################################### 
# 
# 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_170714a_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1568727'
_audit_update_record             
;
2017-08-14 deposited with the CCDC.
2017-09-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 N O3 S'
_chemical_formula_weight         265.32

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.8995(14)
_cell_length_b                   8.3725(8)
_cell_length_c                   9.9537(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.406(3)
_cell_angle_gamma                90
_cell_volume                     1303.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      27.17

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   0.6660
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.248
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13133
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.202
_diffrn_reflns_theta_max         26.016
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2537
_reflns_number_gt                1908
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0004P)²+1.9268P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0147(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2537
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0708
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_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
S1 S 0.60755(5) 0.33124(13) 0.33103(8) 0.0580(3) Uani 1 1 d . . . . .
O1 O 0.65557(16) 0.2756(5) 0.2317(2) 0.0907(11) Uani 1 1 d . . . . .
O2 O 0.52781(16) 0.4089(4) 0.2823(3) 0.0937(10) Uani 1 1 d . . . . .
O3 O 0.84370(14) 0.2046(3) 0.6594(2) 0.0498(6) Uani 1 1 d . . . . .
N1 N 0.79645(15) 0.3042(3) 0.4483(3) 0.0410(6) Uani 1 1 d . . . . .
C1 C 0.80609(19) 0.5530(4) 0.5811(3) 0.0405(7) Uani 1 1 d . . . . .
C2 C 0.8946(2) 0.5547(4) 0.5987(3) 0.0474(8) Uani 1 1 d . . . . .
H2 H 0.922595 0.479471 0.553999 0.057 Uiso 1 1 calc R U . . .
C3 C 0.9414(2) 0.6669(5) 0.6820(4) 0.0633(10) Uani 1 1 d . . . . .
H3 H 1.000832 0.666480 0.694362 0.076 Uiso 1 1 calc R U . . .
C4 C 0.9000(3) 0.7787(5) 0.7462(4) 0.0742(12) Uani 1 1 d . . . . .
H4 H 0.931612 0.854293 0.802567 0.089 Uiso 1 1 calc R U . . .
C5 C 0.8132(3) 0.7806(5) 0.7286(4) 0.0722(12) Uani 1 1 d . . . . .
H5 H 0.786208 0.858017 0.772690 0.087 Uiso 1 1 calc R U . . .
C6 C 0.7644(2) 0.6694(4) 0.6463(3) 0.0544(9) Uani 1 1 d . . . . .
C7 C 0.6685(2) 0.6640(5) 0.6281(4) 0.0708(11) Uani 1 1 d . . . . .
H7A H 0.647295 0.769276 0.645348 0.085 Uiso 1 1 calc R U . . .
H7B H 0.652067 0.590909 0.694344 0.085 Uiso 1 1 calc R U . . .
C8 C 0.6280(2) 0.6112(5) 0.4863(4) 0.0691(11) Uani 1 1 d . . . . .
H8A H 0.567804 0.589673 0.483663 0.083 Uiso 1 1 calc R U . . .
H8B H 0.632602 0.696266 0.421905 0.083 Uiso 1 1 calc R U . . .
C9 C 0.67064(19) 0.4642(4) 0.4455(3) 0.0465(8) Uani 1 1 d . . . . .
C10 C 0.75400(18) 0.4373(4) 0.4913(3) 0.0384(7) Uani 1 1 d . . . . .
C11 C 0.5873(3) 0.1689(5) 0.4273(4) 0.0761(12) Uani 1 1 d . . . . .
H11A H 0.560523 0.204511 0.501080 0.114 Uiso 1 1 calc R U . . .
H11B H 0.640057 0.116058 0.463563 0.114 Uiso 1 1 calc R U . . .
H11C H 0.549907 0.095979 0.370766 0.114 Uiso 1 1 calc R U . . .
C12 C 0.83909(17) 0.1951(4) 0.5363(3) 0.0390(7) Uani 1 1 d . . . . .
C13 C 0.8803(3) 0.0640(5) 0.4690(4) 0.0665(11) Uani 1 1 d . . . . .
H13A H 0.937921 0.048839 0.516323 0.100 Uiso 1 1 calc R U . . .
H13B H 0.880751 0.092102 0.375676 0.100 Uiso 1 1 calc R U . . .
H13C H 0.848584 -0.033187 0.471965 0.100 Uiso 1 1 calc R U . . .
H1 H 0.7896(18) 0.289(4) 0.365(3) 0.040(9) Uiso 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
S1 O2 1.429(3) . ?
S1 O1 1.431(3) . ?
S1 C11 1.726(4) . ?
S1 C9 1.769(3) . ?
O3 C12 1.217(3) . ?
N1 C12 1.359(4) . ?
N1 C10 1.409(4) . ?
N1 H1 0.82(3) . ?
C1 C2 1.386(4) . ?
C1 C6 1.402(4) . ?
C1 C10 1.468(4) . ?
C2 C3 1.379(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.503(5) . ?
C7 C8 1.507(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.496(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.340(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.497(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
O2 S1 O1 117.69(18) . . ?
O2 S1 C11 107.6(2) . . ?
O1 S1 C11 107.7(2) . . ?
O2 S1 C9 107.31(18) . . ?
O1 S1 C9 109.76(16) . . ?
C11 S1 C9 106.18(16) . . ?
C12 N1 C10 123.1(2) . . ?
C12 N1 H1 120(2) . . ?
C10 N1 H1 116(2) . . ?
C2 C1 C6 119.2(3) . . ?
C2 C1 C10 122.1(3) . . ?
C6 C1 C10 118.6(3) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.1(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 C7 122.7(3) . . ?
C1 C6 C7 118.5(3) . . ?
C6 C7 C8 112.0(3) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 111.0(3) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 S1 121.6(3) . . ?
C8 C9 S1 117.4(2) . . ?
C9 C10 N1 121.8(3) . . ?
C9 C10 C1 120.7(3) . . ?
N1 C10 C1 117.3(2) . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N1 122.5(3) . . ?
O3 C12 C13 123.1(3) . . ?
N1 C12 C13 114.4(3) . . ?
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 . . ?

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 1.6(5) . . . . ?
C10 C1 C2 C3 178.8(3) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C4 C5 C6 C1 0.3(6) . . . . ?
C4 C5 C6 C7 177.8(4) . . . . ?
C2 C1 C6 C5 -1.3(5) . . . . ?
C10 C1 C6 C5 -178.6(3) . . . . ?
C2 C1 C6 C7 -178.9(3) . . . . ?
C10 C1 C6 C7 3.7(4) . . . . ?
C5 C6 C7 C8 146.3(4) . . . . ?
C1 C6 C7 C8 -36.2(5) . . . . ?
C6 C7 C8 C9 48.3(5) . . . . ?
C7 C8 C9 C10 -31.6(5) . . . . ?
C7 C8 C9 S1 150.2(3) . . . . ?
O2 S1 C9 C10 -168.9(3) . . . . ?
O1 S1 C9 C10 -39.9(3) . . . . ?
C11 S1 C9 C10 76.2(3) . . . . ?
O2 S1 C9 C8 9.3(3) . . . . ?
O1 S1 C9 C8 138.3(3) . . . . ?
C11 S1 C9 C8 -105.6(3) . . . . ?
C8 C9 C10 N1 -176.5(3) . . . . ?
S1 C9 C10 N1 1.6(4) . . . . ?
C8 C9 C10 C1 -1.0(5) . . . . ?
S1 C9 C10 C1 177.1(2) . . . . ?
C12 N1 C10 C9 -123.4(3) . . . . ?
C12 N1 C10 C1 61.0(4) . . . . ?
C2 C1 C10 C9 -161.0(3) . . . . ?
C6 C1 C10 C9 16.2(4) . . . . ?
C2 C1 C10 N1 14.7(4) . . . . ?
C6 C1 C10 N1 -168.1(3) . . . . ?
C10 N1 C12 O3 0.0(5) . . . . ?
C10 N1 C12 C13 -179.5(3) . . . . ?

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
C11 H11A O1 0.96 2.52 3.064(4) 116.3 4_566
C11 H11C O2 0.96 2.37 3.326(5) 172.9 2_645
N1 H1 O1 0.82(3) 2.30(3) 2.824(3) 122(2) .
N1 H1 O3 0.82(3) 2.36(3) 3.101(3) 150(3) 4_565

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.050



