# 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_a61108a
_database_code_depnum_ccdc_archive 'CCDC 1555192'
_audit_update_record             
;
2017-06-09 deposited with the CCDC.
2017-07-28 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            'C23 H22 Br N O4 S'
_chemical_formula_weight         488.38

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'
Br Br -0.2901 2.4595 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.723(16)
_cell_length_b                   9.856(15)
_cell_length_c                   20.94(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.205(17)
_cell_angle_gamma                90
_cell_volume                     2178(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2177
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      22.70

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    2.013
_shelx_estimated_absorpt_T_min   0.613
_shelx_estimated_absorpt_T_max   0.701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.378
_exptl_absorpt_correction_T_max  0.837
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            10093
_diffrn_reflns_av_unetI/netI     0.1125
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.976
_diffrn_reflns_theta_max         26.009
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             4148
_reflns_number_gt                1861
_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 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)+(0.2000P)²] 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       0.027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4148
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1743
_refine_ls_R_factor_gt           0.0976
_refine_ls_wR_factor_ref         0.3288
_refine_ls_wR_factor_gt          0.2577
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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
Br1 Br 0.35253(12) 0.23372(11) 1.11333(5) 0.0834(6) Uani 1 1 d . . . . .
S1 S 0.2828(2) 0.80015(19) 0.85051(11) 0.0601(8) Uani 1 1 d . . . . .
N1 N 0.1302(8) 0.7826(5) 0.8306(4) 0.062(2) Uani 1 1 d . . . . .
H1 H 0.0830 0.8524 0.8198 0.074 Uiso 1 1 calc R U . . .
O1 O 0.3060(7) 0.9407(5) 0.8425(3) 0.077(2) Uani 1 1 d . . . . .
O2 O 0.3405(7) 0.7007(5) 0.8165(3) 0.0708(19) Uani 1 1 d . . . . .
O3 O -0.1664(6) 0.2308(5) 0.7756(3) 0.0577(16) Uani 1 1 d . . . . .
O4 O -0.0321(5) 0.0167(5) 0.8445(3) 0.0533(15) Uani 1 1 d . . . . .
C1 C 0.0740(8) 0.6496(6) 0.8311(4) 0.050(2) Uani 1 1 d . . . . .
C2 C 0.0810(7) 0.5609(7) 0.7823(4) 0.050(2) Uani 1 1 d . . . . .
H2 H 0.1208 0.5864 0.7481 0.060 Uiso 1 1 calc R U . . .
C3 C 0.0298(8) 0.4347(7) 0.7832(4) 0.051(2) Uani 1 1 d . . . . .
H3 H 0.0367 0.3740 0.7500 0.061 Uiso 1 1 calc R U . . .
C4 C -0.0325(8) 0.3954(7) 0.8329(4) 0.0443(18) Uani 1 1 d . . . . .
C5 C -0.0382(8) 0.4868(7) 0.8820(4) 0.056(2) Uani 1 1 d . . . . .
H5 H -0.0791 0.4623 0.9160 0.068 Uiso 1 1 calc R U . . .
C6 C 0.0154(9) 0.6139(7) 0.8818(4) 0.063(2) Uani 1 1 d . . . . .
H6 H 0.0119 0.6744 0.9155 0.075 Uiso 1 1 calc R U . . .
C7 C -0.0820(8) 0.2552(6) 0.8351(4) 0.0435(19) Uani 1 1 d . . . . .
H7 H -0.1299 0.2492 0.8707 0.052 Uiso 1 1 calc R U . . .
C8 C 0.0210(7) 0.1504(6) 0.8455(4) 0.046(2) Uani 1 1 d . . . . .
H8 H 0.0713 0.1579 0.8109 0.055 Uiso 1 1 calc R U . . .
C9 C -0.1138(9) -0.0043(8) 0.7835(4) 0.067(3) Uani 1 1 d . . . . .
H9A H -0.1498 -0.0948 0.7822 0.080 Uiso 1 1 calc R U . . .
H9B H -0.0653 0.0030 0.7487 0.080 Uiso 1 1 calc R U . . .
C10 C -0.2167(9) 0.0973(8) 0.7740(5) 0.069(3) Uani 1 1 d . . . . .
H10A H -0.2714 0.0818 0.7325 0.082 Uiso 1 1 calc R U . . .
H10B H -0.2671 0.0875 0.8078 0.082 Uiso 1 1 calc R U . . .
C11 C 0.1080(7) 0.1682(6) 0.9111(3) 0.0395(18) Uani 1 1 d . . . . .
C12 C 0.2270(8) 0.2216(7) 0.9162(4) 0.049(2) Uani 1 1 d . . . . .
H12 H 0.2586 0.2446 0.8790 0.059 Uiso 1 1 calc R U . . .
C13 C 0.2995(10) 0.2411(7) 0.9760(5) 0.057(2) Uani 1 1 d . . . . .
H13 H 0.3805 0.2771 0.9791 0.069 Uiso 1 1 calc R U . . .
C14 C 0.2548(8) 0.2083(7) 1.0320(4) 0.049(2) Uani 1 1 d . . . . .
C15 C 0.1362(9) 0.1547(7) 1.0267(4) 0.055(2) Uani 1 1 d . . . . .
H15 H 0.1057 0.1303 1.0640 0.066 Uiso 1 1 calc R U . . .
C16 C 0.0601(8) 0.1361(7) 0.9663(4) 0.0472(19) Uani 1 1 d . . . . .
H16 H -0.0218 0.1025 0.9630 0.057 Uiso 1 1 calc R U . . .
C17 C 0.3213(9) 0.7624(7) 0.9325(4) 0.054(2) Uani 1 1 d . . . . .
C18 C 0.3387(10) 0.8655(8) 0.9784(4) 0.066(3) Uani 1 1 d . . . . .
H18 H 0.3268 0.9552 0.9649 0.079 Uiso 1 1 calc R U . . .
C19 C 0.3731(10) 0.8370(9) 1.0431(4) 0.073(3) Uani 1 1 d . . . . .
H19 H 0.3897 0.9072 1.0731 0.087 Uiso 1 1 calc R U . . .
C20 C 0.3830(10) 0.7042(9) 1.0637(5) 0.066(3) Uani 1 1 d . . . . .
C21 C 0.3646(10) 0.6033(9) 1.0193(5) 0.080(3) Uani 1 1 d . . . . .
H21 H 0.3722 0.5135 1.0332 0.096 Uiso 1 1 calc R U . . .
C22 C 0.3354(9) 0.6304(8) 0.9551(5) 0.067(3) Uani 1 1 d . . . . .
H22 H 0.3246 0.5591 0.9256 0.081 Uiso 1 1 calc R U . . .
C23 C 0.4232(12) 0.6739(13) 1.1350(5) 0.096(4) Uani 1 1 d . . . . .
H23A H 0.3508 0.6462 1.1529 0.144 Uiso 1 1 calc R U . . .
H23B H 0.4596 0.7538 1.1570 0.144 Uiso 1 1 calc R U . . .
H23C H 0.4850 0.6023 1.1404 0.144 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
Br1 C14 1.853(9) . ?
S1 O2 1.417(6) . ?
S1 O1 1.422(5) . ?
S1 N1 1.625(9) . ?
S1 C17 1.734(10) . ?
N1 C1 1.444(9) . ?
O3 C10 1.420(9) . ?
O3 C7 1.425(10) . ?
O4 C9 1.430(10) . ?
O4 C8 1.434(8) . ?
C1 C2 1.358(10) . ?
C1 C6 1.372(11) . ?
C2 C3 1.361(9) . ?
C3 C4 1.387(10) . ?
C4 C5 1.377(10) . ?
C4 C7 1.484(9) . ?
C5 C6 1.379(11) . ?
C7 C8 1.500(11) . ?
C8 C11 1.527(10) . ?
C9 C10 1.477(12) . ?
C11 C12 1.368(11) . ?
C11 C16 1.382(10) . ?
C12 C13 1.366(13) . ?
C13 C14 1.380(12) . ?
C14 C15 1.363(12) . ?
C15 C16 1.391(11) . ?
C17 C22 1.383(10) . ?
C17 C18 1.387(11) . ?
C18 C19 1.370(12) . ?
C19 C20 1.376(12) . ?
C20 C21 1.352(13) . ?
C20 C23 1.508(14) . ?
C21 C22 1.352(13) . ?

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 120.9(4) . . ?
O2 S1 N1 107.9(4) . . ?
O1 S1 N1 105.2(4) . . ?
O2 S1 C17 107.5(4) . . ?
O1 S1 C17 108.1(4) . . ?
N1 S1 C17 106.4(4) . . ?
C1 N1 S1 119.8(5) . . ?
C10 O3 C7 110.9(6) . . ?
C9 O4 C8 109.0(6) . . ?
C2 C1 C6 120.8(7) . . ?
C2 C1 N1 120.0(7) . . ?
C6 C1 N1 119.2(7) . . ?
C1 C2 C3 120.1(7) . . ?
C2 C3 C4 121.0(7) . . ?
C5 C4 C3 118.0(7) . . ?
C5 C4 C7 121.4(7) . . ?
C3 C4 C7 120.4(6) . . ?
C4 C5 C6 121.2(7) . . ?
C1 C6 C5 118.9(7) . . ?
O3 C7 C4 107.8(6) . . ?
O3 C7 C8 110.4(6) . . ?
C4 C7 C8 112.8(7) . . ?
O4 C8 C7 110.5(6) . . ?
O4 C8 C11 107.3(6) . . ?
C7 C8 C11 111.6(6) . . ?
O4 C9 C10 110.3(7) . . ?
O3 C10 C9 110.7(8) . . ?
C12 C11 C16 120.1(7) . . ?
C12 C11 C8 121.9(6) . . ?
C16 C11 C8 117.9(7) . . ?
C13 C12 C11 119.8(8) . . ?
C12 C13 C14 121.3(9) . . ?
C15 C14 C13 118.8(8) . . ?
C15 C14 Br1 119.6(7) . . ?
C13 C14 Br1 121.6(7) . . ?
C14 C15 C16 120.8(7) . . ?
C11 C16 C15 119.1(7) . . ?
C22 C17 C18 117.3(9) . . ?
C22 C17 S1 122.2(7) . . ?
C18 C17 S1 120.5(6) . . ?
C19 C18 C17 121.0(8) . . ?
C18 C19 C20 119.8(8) . . ?
C21 C20 C19 119.4(9) . . ?
C21 C20 C23 121.1(9) . . ?
C19 C20 C23 119.4(9) . . ?
C20 C21 C22 121.2(8) . . ?
C21 C22 C17 121.2(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C1 47.6(7) . . . . ?
O1 S1 N1 C1 177.8(6) . . . . ?
C17 S1 N1 C1 -67.6(7) . . . . ?
S1 N1 C1 C2 -76.6(10) . . . . ?
S1 N1 C1 C6 102.6(9) . . . . ?
C6 C1 C2 C3 -0.2(14) . . . . ?
N1 C1 C2 C3 179.0(8) . . . . ?
C1 C2 C3 C4 1.4(13) . . . . ?
C2 C3 C4 C5 -1.5(13) . . . . ?
C2 C3 C4 C7 -176.8(8) . . . . ?
C3 C4 C5 C6 0.4(13) . . . . ?
C7 C4 C5 C6 175.7(8) . . . . ?
C2 C1 C6 C5 -0.9(14) . . . . ?
N1 C1 C6 C5 179.9(8) . . . . ?
C4 C5 C6 C1 0.8(14) . . . . ?
C10 O3 C7 C4 179.4(7) . . . . ?
C10 O3 C7 C8 55.8(8) . . . . ?
C5 C4 C7 O3 127.9(8) . . . . ?
C3 C4 C7 O3 -57.0(10) . . . . ?
C5 C4 C7 C8 -110.0(9) . . . . ?
C3 C4 C7 C8 65.2(10) . . . . ?
C9 O4 C8 C7 58.5(8) . . . . ?
C9 O4 C8 C11 -179.6(6) . . . . ?
O3 C7 C8 O4 -56.9(8) . . . . ?
C4 C7 C8 O4 -177.5(6) . . . . ?
O3 C7 C8 C11 -176.2(6) . . . . ?
C4 C7 C8 C11 63.1(8) . . . . ?
C8 O4 C9 C10 -59.6(9) . . . . ?
C7 O3 C10 C9 -57.2(10) . . . . ?
O4 C9 C10 O3 59.3(10) . . . . ?
O4 C8 C11 C12 133.7(7) . . . . ?
C7 C8 C11 C12 -105.0(8) . . . . ?
O4 C8 C11 C16 -50.1(8) . . . . ?
C7 C8 C11 C16 71.1(8) . . . . ?
C16 C11 C12 C13 1.1(11) . . . . ?
C8 C11 C12 C13 177.2(6) . . . . ?
C11 C12 C13 C14 -0.3(11) . . . . ?
C12 C13 C14 C15 0.5(11) . . . . ?
C12 C13 C14 Br1 179.7(6) . . . . ?
C13 C14 C15 C16 -1.5(11) . . . . ?
Br1 C14 C15 C16 179.2(5) . . . . ?
C12 C11 C16 C15 -2.1(10) . . . . ?
C8 C11 C16 C15 -178.3(6) . . . . ?
C14 C15 C16 C11 2.3(11) . . . . ?
O2 S1 C17 C22 -33.8(9) . . . . ?
O1 S1 C17 C22 -165.9(8) . . . . ?
N1 S1 C17 C22 81.6(8) . . . . ?
O2 S1 C17 C18 146.4(8) . . . . ?
O1 S1 C17 C18 14.4(9) . . . . ?
N1 S1 C17 C18 -98.2(8) . . . . ?
C22 C17 C18 C19 2.4(16) . . . . ?
S1 C17 C18 C19 -177.9(8) . . . . ?
C17 C18 C19 C20 -4.1(16) . . . . ?
C18 C19 C20 C21 3.2(16) . . . . ?
C18 C19 C20 C23 178.9(10) . . . . ?
C19 C20 C21 C22 -0.7(17) . . . . ?
C23 C20 C21 C22 -176.3(10) . . . . ?
C20 C21 C22 C17 -1.0(16) . . . . ?
C18 C17 C22 C21 0.2(15) . . . . ?
S1 C17 C22 C21 -179.6(8) . . . . ?

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 O4 0.86 2.15 2.935(9) 150.9 1_565

_refine_diff_density_max         0.884
_refine_diff_density_min         -2.011
_refine_diff_density_rms         0.176



####################################################################### 
# 
# 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_70427a
_database_code_depnum_ccdc_archive 'CCDC 1555194'
_audit_update_record             
;
2017-06-09 deposited with the CCDC.
2017-07-28 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            'C17 H21 N O4 S'
_chemical_formula_weight         335.41

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   13.746(2)
_cell_length_b                   8.2548(13)
_cell_length_c                   15.646(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.468(2)
_cell_angle_gamma                90
_cell_volume                     1719.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4846
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      28.64

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.330
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            12064
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.275
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3930
_reflns_number_gt                3210
_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 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)+(0.0827P)²+0.4166P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3930
_refine_ls_number_parameters     215
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.003
_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 0.44040(3) 1.27994(5) 1.07005(3) 0.03496(16) Uani 1 1 d . . . . .
O1 O 0.44698(11) 1.45211(17) 1.08023(11) 0.0504(4) Uani 1 1 d . . . . .
O2 O 0.52317(11) 1.1823(2) 1.11473(12) 0.0558(4) Uani 1 1 d . . . . .
O3 O 0.19899(10) 0.48467(14) 1.10842(8) 0.0347(3) Uani 1 1 d . . . . .
O4 O 0.09287(11) 0.40938(17) 0.93627(10) 0.0435(4) Uani 1 1 d . . . . .
N1 N 0.34112(12) 1.22989(18) 1.10317(11) 0.0333(3) Uani 1 1 d D . . . .
H1 H 0.3027(14) 1.309(2) 1.1017(14) 0.035(5) Uiso 1 1 d D . . . .
C1 C 0.41479(17) 1.2325(3) 0.95721(14) 0.0452(5) Uani 1 1 d . . . . .
H1A H 0.3554 1.2907 0.9256 0.068 Uiso 1 1 calc R U . . .
H1B H 0.4033 1.1169 0.9493 0.068 Uiso 1 1 calc R U . . .
H1C H 0.4715 1.2636 0.9344 0.068 Uiso 1 1 calc R U . . .
C2 C 0.29678(13) 1.07283(19) 1.09073(11) 0.0274(3) Uani 1 1 d . . . . .
C3 C 0.19250(13) 1.0617(2) 1.06724(12) 0.0324(4) Uani 1 1 d . . . . .
H3 H 0.1529 1.1560 1.0585 0.039 Uiso 1 1 calc R U . . .
C4 C 0.14743(13) 0.9101(2) 1.05677(12) 0.0318(4) Uani 1 1 d . . . . .
H4 H 0.0770 0.9026 1.0427 0.038 Uiso 1 1 calc R U . . .
C5 C 0.20445(13) 0.76954(19) 1.06665(11) 0.0273(3) Uani 1 1 d . . . . .
C6 C 0.30816(13) 0.7826(2) 1.09133(12) 0.0296(4) Uani 1 1 d . . . . .
H6 H 0.3476 0.6882 1.0993 0.036 Uiso 1 1 calc R U . . .
C7 C 0.35476(13) 0.9332(2) 1.10452(12) 0.0308(4) Uani 1 1 d . . . . .
H7 H 0.4252 0.9404 1.1227 0.037 Uiso 1 1 calc R U . . .
C8 C 0.15402(13) 0.60613(19) 1.04586(12) 0.0292(4) Uani 1 1 d . . . . .
H8 H 0.0822 0.6167 1.0456 0.035 Uiso 1 1 calc R U . . .
C9 C 0.16192(13) 0.5409(2) 0.95600(12) 0.0315(4) Uani 1 1 d . . . . .
H9 H 0.2306 0.4981 0.9623 0.038 Uiso 1 1 calc R U . . .
C10 C 0.14227(14) 0.6706(2) 0.88556(12) 0.0345(4) Uani 1 1 d . . . . .
C11 C 0.04617(17) 0.7302(3) 0.85028(16) 0.0504(5) Uani 1 1 d . . . . .
H11 H -0.0089 0.6851 0.8674 0.060 Uiso 1 1 calc R U . . .
C12 C 0.0314(2) 0.8561(3) 0.78980(17) 0.0661(8) Uani 1 1 d . . . . .
H12 H -0.0338 0.8964 0.7663 0.079 Uiso 1 1 calc R U . . .
C13 C 0.1118(3) 0.9233(3) 0.76356(16) 0.0682(8) Uani 1 1 d . . . . .
H13 H 0.1012 1.0078 0.7220 0.082 Uiso 1 1 calc R U . . .
C14 C 0.2072(2) 0.8652(3) 0.79886(16) 0.0626(7) Uani 1 1 d . . . . .
H14 H 0.2624 0.9121 0.7828 0.075 Uiso 1 1 calc R U . . .
C15 C 0.22183(17) 0.7385(3) 0.85771(14) 0.0451(5) Uani 1 1 d . . . . .
H15 H 0.2869 0.6967 0.8796 0.054 Uiso 1 1 calc R U . . .
C16 C 0.19258(17) 0.5182(2) 1.19651(13) 0.0429(5) Uani 1 1 d . . . . .
H16A H 0.2311 0.6148 1.2180 0.064 Uiso 1 1 calc R U . . .
H16B H 0.2194 0.4273 1.2344 0.064 Uiso 1 1 calc R U . . .
H16C H 0.1229 0.5352 1.1969 0.064 Uiso 1 1 calc R U . . .
C17 C 0.10159(19) 0.3146(3) 0.86269(17) 0.0562(6) Uani 1 1 d . . . . .
H17A H 0.0882 0.3820 0.8102 0.084 Uiso 1 1 calc R U . . .
H17B H 0.0534 0.2265 0.8540 0.084 Uiso 1 1 calc R U . . .
H17C H 0.1690 0.2708 0.8736 0.084 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 1.4268(16) . ?
S1 O1 1.4304(14) . ?
S1 N1 1.6295(16) . ?
S1 C1 1.756(2) . ?
O3 C8 1.429(2) . ?
O3 C16 1.430(2) . ?
O4 C17 1.422(2) . ?
O4 C9 1.424(2) . ?
N1 C2 1.425(2) . ?
N1 H1 0.838(15) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C7 1.387(2) . ?
C2 C3 1.391(2) . ?
C3 C4 1.388(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.385(2) . ?
C5 C8 1.514(2) . ?
C6 C7 1.390(2) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C8 C9 1.535(2) . ?
C8 H8 0.9900 . ?
C9 C10 1.512(3) . ?
C9 H9 0.9900 . ?
C10 C11 1.388(3) . ?
C10 C15 1.392(3) . ?
C11 C12 1.386(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.387(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.376(4) . ?
C13 H13 0.9400 . ?
C14 C15 1.375(3) . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?

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 119.10(10) . . ?
O2 S1 N1 109.25(9) . . ?
O1 S1 N1 104.55(8) . . ?
O2 S1 C1 107.55(11) . . ?
O1 S1 C1 108.95(10) . . ?
N1 S1 C1 106.84(10) . . ?
C8 O3 C16 113.83(14) . . ?
C17 O4 C9 114.11(16) . . ?
C2 N1 S1 123.43(12) . . ?
C2 N1 H1 117.6(15) . . ?
S1 N1 H1 111.3(15) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 120.03(15) . . ?
C7 C2 N1 121.67(15) . . ?
C3 C2 N1 118.26(15) . . ?
C4 C3 C2 119.39(15) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 121.20(16) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C4 118.65(15) . . ?
C6 C5 C8 120.89(15) . . ?
C4 C5 C8 120.37(15) . . ?
C5 C6 C7 121.01(15) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C6 119.63(15) . . ?
C2 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
O3 C8 C5 112.41(14) . . ?
O3 C8 C9 105.29(13) . . ?
C5 C8 C9 112.09(14) . . ?
O3 C8 H8 109.0 . . ?
C5 C8 H8 109.0 . . ?
C9 C8 H8 109.0 . . ?
O4 C9 C10 113.19(15) . . ?
O4 C9 C8 105.68(13) . . ?
C10 C9 C8 112.25(14) . . ?
O4 C9 H9 108.5 . . ?
C10 C9 H9 108.5 . . ?
C8 C9 H9 108.5 . . ?
C11 C10 C15 118.5(2) . . ?
C11 C10 C9 121.33(18) . . ?
C15 C10 C9 120.13(17) . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 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
O2 S1 N1 C2 -62.23(18) . . . . ?
O1 S1 N1 C2 169.25(15) . . . . ?
C1 S1 N1 C2 53.84(18) . . . . ?
S1 N1 C2 C7 42.5(2) . . . . ?
S1 N1 C2 C3 -139.80(15) . . . . ?
C7 C2 C3 C4 -0.8(3) . . . . ?
N1 C2 C3 C4 -178.49(15) . . . . ?
C2 C3 C4 C5 -2.0(3) . . . . ?
C3 C4 C5 C6 2.9(3) . . . . ?
C3 C4 C5 C8 -173.72(16) . . . . ?
C4 C5 C6 C7 -1.1(3) . . . . ?
C8 C5 C6 C7 175.51(16) . . . . ?
C3 C2 C7 C6 2.5(3) . . . . ?
N1 C2 C7 C6 -179.83(16) . . . . ?
C5 C6 C7 C2 -1.6(3) . . . . ?
C16 O3 C8 C5 61.90(19) . . . . ?
C16 O3 C8 C9 -175.79(14) . . . . ?
C6 C5 C8 O3 44.0(2) . . . . ?
C4 C5 C8 O3 -139.44(16) . . . . ?
C6 C5 C8 C9 -74.4(2) . . . . ?
C4 C5 C8 C9 102.19(18) . . . . ?
C17 O4 C9 C10 67.1(2) . . . . ?
C17 O4 C9 C8 -169.61(17) . . . . ?
O3 C8 C9 O4 70.72(16) . . . . ?
C5 C8 C9 O4 -166.77(14) . . . . ?
O3 C8 C9 C10 -165.45(13) . . . . ?
C5 C8 C9 C10 -42.94(19) . . . . ?
O4 C9 C10 C11 46.8(2) . . . . ?
C8 C9 C10 C11 -72.7(2) . . . . ?
O4 C9 C10 C15 -136.27(18) . . . . ?
C8 C9 C10 C15 104.2(2) . . . . ?
C15 C10 C11 C12 -1.0(3) . . . . ?
C9 C10 C11 C12 176.0(2) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C12 C13 C14 C15 1.9(4) . . . . ?
C13 C14 C15 C10 -2.6(4) . . . . ?
C11 C10 C15 C14 2.1(3) . . . . ?
C9 C10 C15 C14 -174.9(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
N1 H1 O3 0.838(15) 2.053(16) 2.886(2) 172(2) 1_565

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.084



