# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_20181003AR_0m
_database_code_depnum_ccdc_archive 'CCDC 2001038'
loop_
_audit_author_name
_audit_author_address
'Ryan T. VanderLinden '
;University of Utah
United States of America
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 N S'
_chemical_formula_sum            'C16 H15 N S'
_chemical_formula_weight         253.35

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'
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                   12.2588(10)
_cell_length_b                   7.5269(6)
_cell_length_c                   13.4609(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.275(2)
_cell_angle_gamma                90
_cell_volume                     1240.02(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      36.81

_exptl_crystal_description       'hexagonal prism'
_exptl_crystal_colour            'clear and colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.065
_exptl_absorpt_coefficient_mu    0.240
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7012
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_process_details   SADABS-2106/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine focused sealed tube'
_diffrn_measurement_device_type  'BRUKER APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31106
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.314
_diffrn_reflns_theta_max         35.631
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5713
_reflns_number_gt                4999
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0463P)²+0.3211P] 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         5713
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.33862(2) 0.51906(2) 0.56071(2) 0.01327(5) Uani 1 1 d . . . . .
N1 N 0.42405(5) 0.24145(8) 0.67786(4) 0.01154(10) Uani 1 1 d . . . . .
C1 C 0.44926(5) 0.41737(9) 0.64624(5) 0.01096(10) Uani 1 1 d . . . . .
H1 H 0.518645 0.413595 0.610685 0.013 Uiso 1 1 calc R U . . .
C2 C 0.46296(5) 0.54747(9) 0.73110(5) 0.01041(10) Uani 1 1 d . . . . .
C3 C 0.50989(6) 0.71322(9) 0.71415(5) 0.01338(11) Uani 1 1 d . . . . .
H3 H 0.536127 0.739563 0.650748 0.016 Uiso 1 1 calc R U . . .
C4 C 0.51841(6) 0.83965(10) 0.78936(6) 0.01629(12) Uani 1 1 d . . . . .
H4 H 0.549188 0.952878 0.777225 0.020 Uiso 1 1 calc R U . . .
C5 C 0.48146(7) 0.79922(10) 0.88285(6) 0.01724(13) Uani 1 1 d . . . . .
H5 H 0.487243 0.885034 0.934642 0.021 Uiso 1 1 calc R U . . .
C6 C 0.43622(6) 0.63367(10) 0.90035(5) 0.01450(12) Uani 1 1 d . . . . .
H6 H 0.412281 0.606644 0.964513 0.017 Uiso 1 1 calc R U . . .
C7 C 0.42542(5) 0.50609(9) 0.82468(5) 0.01136(11) Uani 1 1 d . . . . .
C8 C 0.37541(6) 0.32682(10) 0.84335(5) 0.01503(12) Uani 1 1 d . . . . .
H8A H 0.313130 0.341823 0.886279 0.018 Uiso 1 1 calc R U . . .
H8AB H 0.430344 0.250383 0.879194 0.018 Uiso 1 1 calc R U . . .
C9 C 0.33567(6) 0.23569(9) 0.74681(5) 0.01391(11) Uani 1 1 d . . . . .
H9A H 0.315662 0.110882 0.760164 0.017 Uiso 1 1 calc R U . . .
H9AB H 0.270298 0.297497 0.717300 0.017 Uiso 1 1 calc R U . . .
C10 C 0.41418(6) 0.11560(9) 0.59548(5) 0.01461(12) Uani 1 1 d . . . . .
H10A H 0.393997 -0.001364 0.622623 0.018 Uiso 1 1 calc R U . . .
H10B H 0.487113 0.102314 0.568352 0.018 Uiso 1 1 calc R U . . .
C11 C 0.33290(5) 0.15980(9) 0.50965(5) 0.01117(10) Uani 1 1 d . . . . .
C12 C 0.29397(6) 0.02137(9) 0.44763(5) 0.01320(11) Uani 1 1 d . . . . .
H12 H 0.316812 -0.096860 0.462205 0.016 Uiso 1 1 calc R U . . .
C13 C 0.22272(6) 0.05262(10) 0.36527(5) 0.01570(12) Uani 1 1 d . . . . .
H13 H 0.197288 -0.043099 0.324187 0.019 Uiso 1 1 calc R U . . .
C14 C 0.18907(6) 0.22622(11) 0.34373(5) 0.01710(13) Uani 1 1 d . . . . .
H14 H 0.140286 0.249186 0.287816 0.021 Uiso 1 1 calc R U . . .
C15 C 0.22696(6) 0.36549(10) 0.40410(5) 0.01517(12) Uani 1 1 d . . . . .
H15 H 0.203942 0.483480 0.389101 0.018 Uiso 1 1 calc R U . . .
C16 C 0.29890(5) 0.33338(9) 0.48701(5) 0.01145(11) 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
S1 C16 1.7661(7) . ?
S1 C1 1.8901(7) . ?
N1 C1 1.4300(9) . ?
N1 C10 1.4582(9) . ?
N1 C9 1.4669(9) . ?
C1 C2 1.5066(9) . ?
C1 H1 1.0000 . ?
C2 C3 1.3980(9) . ?
C2 C7 1.4006(9) . ?
C3 C4 1.3890(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.3952(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.3895(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.4006(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.5091(10) . ?
C8 C9 1.5245(10) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C11 1.5188(10) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.3997(9) . ?
C11 C12 1.4017(10) . ?
C12 C13 1.3916(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.3957(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.3899(11) . ?
C14 H14 0.9500 . ?
C15 C16 1.4034(10) . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 S1 C1 100.77(3) . . ?
C1 N1 C10 112.65(5) . . ?
C1 N1 C9 113.30(5) . . ?
C10 N1 C9 115.45(6) . . ?
N1 C1 C2 113.13(5) . . ?
N1 C1 S1 113.36(5) . . ?
C2 C1 S1 104.10(4) . . ?
N1 C1 H1 108.7 . . ?
C2 C1 H1 108.7 . . ?
S1 C1 H1 108.7 . . ?
C3 C2 C7 120.31(6) . . ?
C3 C2 C1 119.04(6) . . ?
C7 C2 C1 120.61(6) . . ?
C4 C3 C2 120.46(6) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.56(7) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.11(7) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.91(6) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C2 118.64(6) . . ?
C6 C7 C8 120.96(6) . . ?
C2 C7 C8 120.40(6) . . ?
C7 C8 C9 111.92(6) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8AB 109.2 . . ?
C9 C8 H8AB 109.2 . . ?
H8A C8 H8AB 107.9 . . ?
N1 C9 C8 108.32(6) . . ?
N1 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
N1 C9 H9AB 110.0 . . ?
C8 C9 H9AB 110.0 . . ?
H9A C9 H9AB 108.4 . . ?
N1 C10 C11 117.30(6) . . ?
N1 C10 H10A 108.0 . . ?
C11 C10 H10A 108.0 . . ?
N1 C10 H10B 108.0 . . ?
C11 C10 H10B 108.0 . . ?
H10A C10 H10B 107.2 . . ?
C16 C11 C12 118.51(6) . . ?
C16 C11 C10 122.98(6) . . ?
C12 C11 C10 118.45(6) . . ?
C13 C12 C11 121.71(7) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 119.24(7) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 119.98(7) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.59(7) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 119.98(6) . . ?
C11 C16 S1 123.18(5) . . ?
C15 C16 S1 116.81(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
C10 N1 C1 C2 -178.29(5) . . . . ?
C9 N1 C1 C2 48.34(7) . . . . ?
C10 N1 C1 S1 63.47(6) . . . . ?
C9 N1 C1 S1 -69.90(6) . . . . ?
C16 S1 C1 N1 -39.39(5) . . . . ?
C16 S1 C1 C2 -162.74(4) . . . . ?
N1 C1 C2 C3 166.60(6) . . . . ?
S1 C1 C2 C3 -69.90(7) . . . . ?
N1 C1 C2 C7 -15.89(9) . . . . ?
S1 C1 C2 C7 107.61(6) . . . . ?
C7 C2 C3 C4 -0.93(10) . . . . ?
C1 C2 C3 C4 176.59(6) . . . . ?
C2 C3 C4 C5 1.09(11) . . . . ?
C3 C4 C5 C6 -0.16(11) . . . . ?
C4 C5 C6 C7 -0.95(11) . . . . ?
C5 C6 C7 C2 1.10(10) . . . . ?
C5 C6 C7 C8 -179.47(7) . . . . ?
C3 C2 C7 C6 -0.17(10) . . . . ?
C1 C2 C7 C6 -177.65(6) . . . . ?
C3 C2 C7 C8 -179.59(6) . . . . ?
C1 C2 C7 C8 2.93(10) . . . . ?
C6 C7 C8 C9 160.22(6) . . . . ?
C2 C7 C8 C9 -20.36(9) . . . . ?
C1 N1 C9 C8 -66.25(7) . . . . ?
C10 N1 C9 C8 161.74(6) . . . . ?
C7 C8 C9 N1 49.59(8) . . . . ?
C1 N1 C10 C11 -55.69(8) . . . . ?
C9 N1 C10 C11 76.63(8) . . . . ?
N1 C10 C11 C16 24.26(10) . . . . ?
N1 C10 C11 C12 -158.70(6) . . . . ?
C16 C11 C12 C13 -0.27(10) . . . . ?
C10 C11 C12 C13 -177.44(6) . . . . ?
C11 C12 C13 C14 0.01(11) . . . . ?
C12 C13 C14 C15 0.18(11) . . . . ?
C13 C14 C15 C16 -0.11(11) . . . . ?
C12 C11 C16 C15 0.34(10) . . . . ?
C10 C11 C16 C15 177.38(6) . . . . ?
C12 C11 C16 S1 178.19(5) . . . . ?
C10 C11 C16 S1 -4.78(9) . . . . ?
C14 C15 C16 C11 -0.16(11) . . . . ?
C14 C15 C16 S1 -178.14(6) . . . . ?
C1 S1 C16 C11 10.93(6) . . . . ?
C1 S1 C16 C15 -171.16(5) . . . . ?

_refine_diff_density_max         0.593
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.057



####################################################################### 
# 
# 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_20181010AR_P
_database_code_depnum_ccdc_archive 'CCDC 2001039'
loop_
_audit_author_name
_audit_author_address
'Ryan T. VanderLinden '
;University of Utah
United States of America
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 N O S'
_chemical_formula_sum            'C17 H17 N O S'
_chemical_formula_weight         283.37

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                   18.2786(14)
_cell_length_b                   5.5078(4)
_cell_length_c                   13.6680(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.902(2)
_cell_angle_gamma                90
_cell_volume                     1368.73(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    5782
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      33.91

_exptl_crystal_description       'Rhombic prism'
_exptl_crystal_colour            'clear and colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.231
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focused sealed tube'
_diffrn_measurement_device_type  'BRUKER APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24293
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.997
_diffrn_reflns_theta_max         34.877
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5960
_reflns_number_gt                4375
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0475P)²+0.5247P] 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         5960
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.34375(2) 0.75754(5) 0.48034(2) 0.01285(7) Uani 1 1 d . . . . .
O1 O 0.05954(5) 0.32765(17) 0.65734(7) 0.01816(18) Uani 1 1 d . . . . .
N1 N 0.24202(5) 0.69012(18) 0.31552(7) 0.01080(17) Uani 1 1 d . . . . .
C1 C 0.37789(6) 0.9468(2) 0.39136(8) 0.01154(19) Uani 1 1 d . . . . .
C2 C 0.42818(6) 1.1267(2) 0.42660(9) 0.0143(2) Uani 1 1 d . . . . .
H2 H 0.441769 1.141382 0.495321 0.017 Uiso 1 1 calc R U . . .
C3 C 0.45823(7) 1.2832(2) 0.36213(9) 0.0165(2) Uani 1 1 d . . . . .
H3 H 0.492891 1.402652 0.386582 0.020 Uiso 1 1 calc R U . . .
C4 C 0.43759(7) 1.2651(2) 0.26165(9) 0.0167(2) Uani 1 1 d . . . . .
H4 H 0.458673 1.369778 0.216973 0.020 Uiso 1 1 calc R U . . .
C5 C 0.38571(6) 1.0919(2) 0.22708(9) 0.0143(2) Uani 1 1 d . . . . .
H5 H 0.370775 1.083044 0.158515 0.017 Uiso 1 1 calc R U . . .
C6 C 0.35512(6) 0.9314(2) 0.29032(8) 0.01164(19) Uani 1 1 d . . . . .
C7 C 0.29793(6) 0.7486(2) 0.24936(8) 0.01252(19) Uani 1 1 d . . . . .
H7A H 0.272920 0.813086 0.187056 0.015 Uiso 1 1 calc R U . . .
H7AB H 0.323329 0.596913 0.233700 0.015 Uiso 1 1 calc R U . . .
C8 C 0.19802(6) 0.9021(2) 0.33778(8) 0.0124(2) Uani 1 1 d . . . . .
H8A H 0.180340 0.986394 0.275849 0.015 Uiso 1 1 calc R U . . .
H8AB H 0.229075 1.016935 0.379461 0.015 Uiso 1 1 calc R U . . .
C9 C 0.13245(6) 0.8261(2) 0.39100(8) 0.0123(2) Uani 1 1 d . . . . .
H9A H 0.113842 0.969715 0.424257 0.015 Uiso 1 1 calc R U . . .
H9AB H 0.092659 0.768373 0.341902 0.015 Uiso 1 1 calc R U . . .
C10 C 0.15044(6) 0.6286(2) 0.46627(8) 0.01049(19) Uani 1 1 d . . . . .
C11 C 0.09949(6) 0.5631(2) 0.53046(8) 0.0128(2) Uani 1 1 d . . . . .
H11 H 0.054337 0.649152 0.528787 0.015 Uiso 1 1 calc R U . . .
C12 C 0.11358(6) 0.3736(2) 0.59710(8) 0.0126(2) Uani 1 1 d . . . . .
C13 C 0.17944(6) 0.2443(2) 0.60052(8) 0.01295(19) Uani 1 1 d . . . . .
H13 H 0.189273 0.114159 0.645560 0.016 Uiso 1 1 calc R U . . .
C14 C 0.23033(6) 0.3105(2) 0.53641(8) 0.01143(19) Uani 1 1 d . . . . .
H14 H 0.275376 0.223869 0.538012 0.014 Uiso 1 1 calc R U . . .
C15 C 0.21687(6) 0.5008(2) 0.46993(8) 0.01039(19) Uani 1 1 d . . . . .
C16 C 0.27349(6) 0.5683(2) 0.40248(8) 0.01100(19) Uani 1 1 d . . . . .
H16 H 0.297980 0.416461 0.382447 0.013 Uiso 1 1 calc R U . . .
C17 C 0.06988(7) 0.1221(2) 0.72084(10) 0.0189(2) Uani 1 1 d . . . . .
H17A H 0.027586 0.105871 0.758983 0.028 Uiso 1 1 calc R U . . .
H17B H 0.114757 0.143953 0.765741 0.028 Uiso 1 1 calc R U . . .
H17C H 0.074410 -0.024716 0.681396 0.028 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 C1 1.7638(12) . ?
S1 C16 1.8940(11) . ?
O1 C12 1.3729(14) . ?
O1 C17 1.4274(15) . ?
N1 C16 1.4328(14) . ?
N1 C8 1.4674(15) . ?
N1 C7 1.4684(14) . ?
C1 C2 1.4028(16) . ?
C1 C6 1.4032(16) . ?
C2 C3 1.3859(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3900(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3927(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3931(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.5164(16) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C9 1.5232(16) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.5100(16) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C11 1.3912(16) . ?
C10 C15 1.3997(15) . ?
C11 C12 1.3918(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3953(16) . ?
C13 C14 1.3907(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3923(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.5018(15) . ?
C16 H16 1.0000 . ?
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
C1 S1 C16 101.84(5) . . ?
C12 O1 C17 116.90(10) . . ?
C16 N1 C8 112.49(9) . . ?
C16 N1 C7 111.61(9) . . ?
C8 N1 C7 112.58(9) . . ?
C2 C1 C6 119.87(11) . . ?
C2 C1 S1 116.51(9) . . ?
C6 C1 S1 123.56(9) . . ?
C3 C2 C1 120.64(11) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.90(11) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 119.38(11) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 121.78(11) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 118.36(11) . . ?
C5 C6 C7 119.84(10) . . ?
C1 C6 C7 121.79(10) . . ?
N1 C7 C6 114.54(9) . . ?
N1 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
N1 C7 H7AB 108.6 . . ?
C6 C7 H7AB 108.6 . . ?
H7A C7 H7AB 107.6 . . ?
N1 C8 C9 110.80(9) . . ?
N1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N1 C8 H8AB 109.5 . . ?
C9 C8 H8AB 109.5 . . ?
H8A C8 H8AB 108.1 . . ?
C10 C9 C8 113.36(9) . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9AB 108.9 . . ?
C8 C9 H9AB 108.9 . . ?
H9A C9 H9AB 107.7 . . ?
C11 C10 C15 118.79(10) . . ?
C11 C10 C9 120.23(10) . . ?
C15 C10 C9 120.91(10) . . ?
C10 C11 C12 121.09(10) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
O1 C12 C11 115.76(10) . . ?
O1 C12 C13 123.87(10) . . ?
C11 C12 C13 120.37(10) . . ?
C14 C13 C12 118.41(10) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 121.59(10) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C10 119.75(10) . . ?
C14 C15 C16 120.01(10) . . ?
C10 C15 C16 120.24(10) . . ?
N1 C16 C15 112.45(9) . . ?
N1 C16 S1 113.55(8) . . ?
C15 C16 S1 105.16(7) . . ?
N1 C16 H16 108.5 . . ?
C15 C16 H16 108.5 . . ?
S1 C16 H16 108.5 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 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
C16 S1 C1 C2 175.10(9) . . . . ?
C16 S1 C1 C6 -2.24(11) . . . . ?
C6 C1 C2 C3 -2.87(17) . . . . ?
S1 C1 C2 C3 179.68(9) . . . . ?
C1 C2 C3 C4 1.08(18) . . . . ?
C2 C3 C4 C5 1.17(18) . . . . ?
C3 C4 C5 C6 -1.68(18) . . . . ?
C4 C5 C6 C1 -0.10(17) . . . . ?
C4 C5 C6 C7 179.05(11) . . . . ?
C2 C1 C6 C5 2.35(16) . . . . ?
S1 C1 C6 C5 179.60(9) . . . . ?
C2 C1 C6 C7 -176.78(10) . . . . ?
S1 C1 C6 C7 0.48(15) . . . . ?
C16 N1 C7 C6 -65.48(12) . . . . ?
C8 N1 C7 C6 62.13(12) . . . . ?
C5 C6 C7 N1 -147.29(10) . . . . ?
C1 C6 C7 N1 31.83(15) . . . . ?
C16 N1 C8 C9 -62.99(12) . . . . ?
C7 N1 C8 C9 169.87(9) . . . . ?
N1 C8 C9 C10 39.89(13) . . . . ?
C8 C9 C10 C11 171.02(10) . . . . ?
C8 C9 C10 C15 -11.91(15) . . . . ?
C15 C10 C11 C12 -0.30(17) . . . . ?
C9 C10 C11 C12 176.83(10) . . . . ?
C17 O1 C12 C11 175.09(11) . . . . ?
C17 O1 C12 C13 -5.38(17) . . . . ?
C10 C11 C12 O1 179.31(10) . . . . ?
C10 C11 C12 C13 -0.23(17) . . . . ?
O1 C12 C13 C14 -179.14(11) . . . . ?
C11 C12 C13 C14 0.37(17) . . . . ?
C12 C13 C14 C15 0.02(17) . . . . ?
C13 C14 C15 C10 -0.55(17) . . . . ?
C13 C14 C15 C16 179.47(10) . . . . ?
C11 C10 C15 C14 0.68(16) . . . . ?
C9 C10 C15 C14 -176.43(10) . . . . ?
C11 C10 C15 C16 -179.34(10) . . . . ?
C9 C10 C15 C16 3.55(16) . . . . ?
C8 N1 C16 C15 53.88(12) . . . . ?
C7 N1 C16 C15 -178.46(9) . . . . ?
C8 N1 C16 S1 -65.38(11) . . . . ?
C7 N1 C16 S1 62.27(10) . . . . ?
C14 C15 C16 N1 156.11(10) . . . . ?
C10 C15 C16 N1 -23.87(14) . . . . ?
C14 C15 C16 S1 -79.84(11) . . . . ?
C10 C15 C16 S1 100.18(10) . . . . ?
C1 S1 C16 N1 -28.24(9) . . . . ?
C1 S1 C16 C15 -151.58(7) . . . . ?

_refine_diff_density_max         0.598
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.071



####################################################################### 
# 
# 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_20181011AR_0m
_database_code_depnum_ccdc_archive 'CCDC 2001040'
loop_
_audit_author_name
_audit_author_address
'Ryan T. VanderLinden '
;University of Utah
United States of America
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 N2 O3 S'
_chemical_formula_sum            'C17 H16 N2 O3 S'
_chemical_formula_weight         328.38

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.2999(3)
_cell_length_b                   8.7882(3)
_cell_length_c                   12.8272(5)
_cell_angle_alpha                70.7810(10)
_cell_angle_beta                 74.6590(10)
_cell_angle_gamma                80.3970(10)
_cell_volume                     746.48(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    9847
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      39.65

_exptl_crystal_description       'rhombic prism'
_exptl_crystal_colour            'clear and colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7122
_exptl_absorpt_correction_T_max  0.7480
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focused sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52965
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.464
_diffrn_reflns_theta_max         37.784
_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             7991
_reflns_number_gt                6454
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0493P)²+0.1762P] 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         7991
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.62664(3) 0.54997(2) 0.20377(2) 0.01347(5) Uani 1 1 d . . . . .
O1 O 0.82946(9) 0.92720(8) 0.48824(5) 0.01674(11) Uani 1 1 d . . . . .
O2 O 0.00488(10) 0.24633(9) 0.04584(7) 0.02276(14) Uani 1 1 d . . . . .
O3 O 0.24476(10) 0.06559(8) 0.03751(6) 0.01970(12) Uani 1 1 d . . . . .
N1 N 0.27126(9) 0.70936(8) 0.26364(6) 0.01214(11) Uani 1 1 d . . . . .
N2 N 0.16689(10) 0.19170(9) 0.05763(6) 0.01371(11) Uani 1 1 d . . . . .
C1 C 0.48031(10) 0.45210(9) 0.16282(6) 0.01116(12) Uani 1 1 d . . . . .
C2 C 0.56253(11) 0.30914(9) 0.13699(7) 0.01310(12) Uani 1 1 d . . . . .
H2 H 0.690284 0.271430 0.142794 0.016 Uiso 1 1 calc R U . . .
C3 C 0.46004(11) 0.22261(9) 0.10324(7) 0.01322(12) Uani 1 1 d . . . . .
H3 H 0.515414 0.125807 0.085547 0.016 Uiso 1 1 calc R U . . .
C4 C 0.27361(11) 0.28111(9) 0.09589(6) 0.01148(12) Uani 1 1 d . . . . .
C5 C 0.18701(11) 0.42001(9) 0.12353(6) 0.01176(12) Uani 1 1 d . . . . .
H5 H 0.058331 0.455330 0.118881 0.014 Uiso 1 1 calc R U . . .
C6 C 0.28961(11) 0.50753(9) 0.15817(6) 0.01088(11) Uani 1 1 d . . . . .
C7 C 0.19278(11) 0.66027(10) 0.18697(7) 0.01360(13) Uani 1 1 d . . . . .
H7A H 0.199482 0.750193 0.115470 0.016 Uiso 1 1 calc R U . . .
H7AB H 0.056329 0.644373 0.221508 0.016 Uiso 1 1 calc R U . . .
C8 C 0.23352(12) 0.60571(10) 0.38126(7) 0.01423(13) Uani 1 1 d . . . . .
H8A H 0.310134 0.500407 0.386459 0.017 Uiso 1 1 calc R U . . .
H8AB H 0.097070 0.585251 0.406987 0.017 Uiso 1 1 calc R U . . .
C9 C 0.28397(12) 0.68640(10) 0.45758(7) 0.01525(13) Uani 1 1 d . . . . .
H9A H 0.181714 0.771685 0.471203 0.018 Uiso 1 1 calc R U . . .
H9AB H 0.289440 0.604874 0.531656 0.018 Uiso 1 1 calc R U . . .
C10 C 0.47187(11) 0.76076(9) 0.40792(6) 0.01204(12) Uani 1 1 d . . . . .
C11 C 0.56202(11) 0.80385(10) 0.47659(7) 0.01296(12) Uani 1 1 d . . . . .
H11 H 0.508347 0.780901 0.555579 0.016 Uiso 1 1 calc R U . . .
C12 C 0.72998(11) 0.88018(9) 0.42933(7) 0.01270(12) Uani 1 1 d . . . . .
C13 C 0.80889(11) 0.91604(10) 0.31310(7) 0.01408(13) Uani 1 1 d . . . . .
H13 H 0.922496 0.969770 0.280788 0.017 Uiso 1 1 calc R U . . .
C14 C 0.72038(11) 0.87272(10) 0.24542(7) 0.01282(12) Uani 1 1 d . . . . .
H14 H 0.774180 0.896176 0.166422 0.015 Uiso 1 1 calc R U . . .
C15 C 0.55234(11) 0.79468(9) 0.29232(6) 0.01146(12) Uani 1 1 d . . . . .
C16 C 0.46714(11) 0.73851(9) 0.21852(6) 0.01163(12) Uani 1 1 d . . . . .
H16 H 0.480431 0.821580 0.142399 0.014 Uiso 1 1 calc R U . . .
C17 C 0.77666(15) 0.87010(11) 0.60875(7) 0.01939(16) Uani 1 1 d . . . . .
H17A H 0.646384 0.914037 0.634978 0.029 Uiso 1 1 calc R U . . .
H17B H 0.864462 0.905291 0.640550 0.029 Uiso 1 1 calc R U . . .
H17C H 0.782801 0.751668 0.633644 0.029 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 C1 1.7487(8) . ?
S1 C16 1.8929(8) . ?
O1 C12 1.3658(9) . ?
O1 C17 1.4242(11) . ?
O2 N2 1.2286(10) . ?
O3 N2 1.2323(9) . ?
N1 C16 1.4255(10) . ?
N1 C8 1.4633(11) . ?
N1 C7 1.4633(10) . ?
N2 C4 1.4579(10) . ?
C1 C2 1.4020(11) . ?
C1 C6 1.4061(10) . ?
C2 C3 1.3796(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.3884(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.3872(11) . ?
C5 C6 1.3940(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.5198(11) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C9 1.5270(11) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.5090(11) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C15 1.3925(11) . ?
C10 C11 1.4007(11) . ?
C11 C12 1.3907(11) . ?
C11 H11 0.9500 . ?
C12 C13 1.3966(11) . ?
C13 C14 1.3829(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.3984(11) . ?
C14 H14 0.9500 . ?
C15 C16 1.4994(10) . ?
C16 H16 1.0000 . ?
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
C1 S1 C16 101.16(3) . . ?
C12 O1 C17 117.52(7) . . ?
C16 N1 C8 113.02(6) . . ?
C16 N1 C7 111.75(6) . . ?
C8 N1 C7 114.93(6) . . ?
O2 N2 O3 123.18(7) . . ?
O2 N2 C4 118.60(7) . . ?
O3 N2 C4 118.22(7) . . ?
C2 C1 C6 120.59(7) . . ?
C2 C1 S1 115.94(6) . . ?
C6 C1 S1 123.45(6) . . ?
C3 C2 C1 120.76(7) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 118.07(7) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C5 C4 C3 122.45(7) . . ?
C5 C4 N2 119.51(7) . . ?
C3 C4 N2 118.04(7) . . ?
C4 C5 C6 119.72(7) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 118.37(7) . . ?
C5 C6 C7 118.91(6) . . ?
C1 C6 C7 122.71(7) . . ?
N1 C7 C6 115.97(6) . . ?
N1 C7 H7A 108.3 . . ?
C6 C7 H7A 108.3 . . ?
N1 C7 H7AB 108.3 . . ?
C6 C7 H7AB 108.3 . . ?
H7A C7 H7AB 107.4 . . ?
N1 C8 C9 110.30(6) . . ?
N1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N1 C8 H8AB 109.6 . . ?
C9 C8 H8AB 109.6 . . ?
H8A C8 H8AB 108.1 . . ?
C10 C9 C8 113.06(7) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9AB 109.0 . . ?
C8 C9 H9AB 109.0 . . ?
H9A C9 H9AB 107.8 . . ?
C15 C10 C11 119.37(7) . . ?
C15 C10 C9 120.26(7) . . ?
C11 C10 C9 120.30(7) . . ?
C12 C11 C10 120.10(7) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
O1 C12 C11 124.95(7) . . ?
O1 C12 C13 114.66(7) . . ?
C11 C12 C13 120.38(7) . . ?
C14 C13 C12 119.49(7) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.54(7) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C14 120.10(7) . . ?
C10 C15 C16 120.41(7) . . ?
C14 C15 C16 119.37(7) . . ?
N1 C16 C15 113.76(6) . . ?
N1 C16 S1 113.00(5) . . ?
C15 C16 S1 102.94(5) . . ?
N1 C16 H16 109.0 . . ?
C15 C16 H16 109.0 . . ?
S1 C16 H16 109.0 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 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
C16 S1 C1 C2 175.93(6) . . . . ?
C16 S1 C1 C6 -5.78(7) . . . . ?
C6 C1 C2 C3 1.96(12) . . . . ?
S1 C1 C2 C3 -179.70(6) . . . . ?
C1 C2 C3 C4 -0.12(12) . . . . ?
C2 C3 C4 C5 -1.48(12) . . . . ?
C2 C3 C4 N2 178.57(7) . . . . ?
O2 N2 C4 C5 3.33(11) . . . . ?
O3 N2 C4 C5 -177.44(7) . . . . ?
O2 N2 C4 C3 -176.72(8) . . . . ?
O3 N2 C4 C3 2.51(11) . . . . ?
C3 C4 C5 C6 1.22(12) . . . . ?
N2 C4 C5 C6 -178.83(7) . . . . ?
C4 C5 C6 C1 0.64(11) . . . . ?
C4 C5 C6 C7 179.41(7) . . . . ?
C2 C1 C6 C5 -2.19(11) . . . . ?
S1 C1 C6 C5 179.60(6) . . . . ?
C2 C1 C6 C7 179.09(7) . . . . ?
S1 C1 C6 C7 0.88(11) . . . . ?
C16 N1 C7 C6 59.47(9) . . . . ?
C8 N1 C7 C6 -71.06(9) . . . . ?
C5 C6 C7 N1 156.10(7) . . . . ?
C1 C6 C7 N1 -25.19(11) . . . . ?
C16 N1 C8 C9 61.95(8) . . . . ?
C7 N1 C8 C9 -168.14(6) . . . . ?
N1 C8 C9 C10 -44.31(9) . . . . ?
C8 C9 C10 C15 18.98(11) . . . . ?
C8 C9 C10 C11 -164.28(7) . . . . ?
C15 C10 C11 C12 0.18(12) . . . . ?
C9 C10 C11 C12 -176.58(7) . . . . ?
C17 O1 C12 C11 11.29(12) . . . . ?
C17 O1 C12 C13 -169.33(8) . . . . ?
C10 C11 C12 O1 -179.95(7) . . . . ?
C10 C11 C12 C13 0.70(12) . . . . ?
O1 C12 C13 C14 179.55(7) . . . . ?
C11 C12 C13 C14 -1.03(12) . . . . ?
C12 C13 C14 C15 0.48(12) . . . . ?
C11 C10 C15 C14 -0.73(11) . . . . ?
C9 C10 C15 C14 176.03(7) . . . . ?
C11 C10 C15 C16 175.27(7) . . . . ?
C9 C10 C15 C16 -7.96(11) . . . . ?
C13 C14 C15 C10 0.40(12) . . . . ?
C13 C14 C15 C16 -175.64(7) . . . . ?
C8 N1 C16 C15 -50.47(9) . . . . ?
C7 N1 C16 C15 178.03(6) . . . . ?
C8 N1 C16 S1 66.44(7) . . . . ?
C7 N1 C16 S1 -65.06(7) . . . . ?
C10 C15 C16 N1 22.98(10) . . . . ?
C14 C15 C16 N1 -160.99(7) . . . . ?
C10 C15 C16 S1 -99.65(7) . . . . ?
C14 C15 C16 S1 76.38(8) . . . . ?
C1 S1 C16 N1 36.96(6) . . . . ?
C1 S1 C16 C15 160.09(5) . . . . ?

_refine_diff_density_max         0.670
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.068



