# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1494031'
_audit_update_record             
;
2016-07-16 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H27 N3 O3 S'
_chemical_formula_weight         389.50

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.474(6)
_cell_length_b                   11.835(5)
_cell_length_c                   26.509(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3914(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1806
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      19.99

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.191
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35897
_diffrn_reflns_av_unetI/netI     0.0738
_diffrn_reflns_av_R_equivalents  0.1485
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.536
_diffrn_reflns_theta_max         25.071
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3464
_reflns_number_gt                2283
_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-2013 (Sheldrick, 2013)'
_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)+(0.0569P)²+2.2487P] 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         3464
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1379
_refine_ls_wR_factor_gt          0.1146
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9981(2) 0.6791(3) 0.47519(11) 0.0240(7) Uani 1 1 d . . . . .
H1 H 1.0320 0.7362 0.4933 0.029 Uiso 1 1 calc R U . . .
C2 C 1.0588(2) 0.5966(3) 0.45182(11) 0.0249(8) Uani 1 1 d . . . . .
H2 H 1.1331 0.5971 0.4549 0.030 Uiso 1 1 calc R U . . .
C3 C 1.0083(2) 0.5129(3) 0.42368(11) 0.0226(7) Uani 1 1 d . . . . .
H3A H 1.0486 0.4575 0.4076 0.027 Uiso 1 1 calc R U . . .
C4 C 0.8976(2) 0.5127(3) 0.41979(11) 0.0187(7) Uani 1 1 d . . . . .
C5 C 0.8352(2) 0.5950(2) 0.44386(10) 0.0165(7) Uani 1 1 d . . . . .
C6 C 0.8873(2) 0.6776(3) 0.47196(11) 0.0221(7) Uani 1 1 d . . . . .
H6 H 0.8474 0.7323 0.4888 0.027 Uiso 1 1 calc R U . . .
C7 C 0.7149(2) 0.5914(3) 0.44618(11) 0.0188(7) Uani 1 1 d . . . . .
C8 C 0.7005(2) 0.5531(2) 0.35483(11) 0.0160(7) Uani 1 1 d . . . . .
C9 C 0.6887(2) 0.6139(3) 0.26649(11) 0.0198(7) Uani 1 1 d . . . . .
H9 H 0.7636 0.5895 0.2640 0.024 Uiso 1 1 calc R U . . .
C10 C 0.6182(2) 0.5268(3) 0.23939(11) 0.0223(7) Uani 1 1 d . . . . .
H10A H 0.6482 0.5115 0.2063 0.027 Uiso 1 1 calc R U . . .
H10B H 0.6188 0.4567 0.2584 0.027 Uiso 1 1 calc R U . . .
C11 C 0.5023(2) 0.5669(3) 0.23332(12) 0.0254(8) Uani 1 1 d . . . . .
H11A H 0.4623 0.5116 0.2140 0.030 Uiso 1 1 calc R U . . .
H11B H 0.4692 0.5733 0.2663 0.030 Uiso 1 1 calc R U . . .
C12 C 0.4975(3) 0.6806(3) 0.20672(12) 0.0260(8) Uani 1 1 d . . . . .
H12A H 0.4235 0.7053 0.2043 0.031 Uiso 1 1 calc R U . . .
H12B H 0.5257 0.6731 0.1728 0.031 Uiso 1 1 calc R U . . .
C13 C 0.5625(2) 0.7684(3) 0.23558(12) 0.0257(8) Uani 1 1 d . . . . .
H13A H 0.5303 0.7805 0.2684 0.031 Uiso 1 1 calc R U . . .
H13B H 0.5609 0.8396 0.2174 0.031 Uiso 1 1 calc R U . . .
C14 C 0.6786(2) 0.7308(3) 0.24228(11) 0.0241(8) Uani 1 1 d . . . . .
H14A H 0.7158 0.7855 0.2632 0.029 Uiso 1 1 calc R U . . .
H14B H 0.7135 0.7296 0.2096 0.029 Uiso 1 1 calc R U . . .
C15 C 0.5393(2) 0.5349(3) 0.41093(11) 0.0203(7) Uani 1 1 d . . . . .
H15 H 0.5309 0.5132 0.4464 0.024 Uiso 1 1 calc R U . . .
C16 C 0.4624(2) 0.6326(3) 0.40189(12) 0.0228(7) Uani 1 1 d . . . . .
H16A H 0.4668 0.6565 0.3670 0.027 Uiso 1 1 calc R U . . .
H16B H 0.4823 0.6961 0.4231 0.027 Uiso 1 1 calc R U . . .
C17 C 0.3474(2) 0.5959(3) 0.41409(13) 0.0278(8) Uani 1 1 d . . . . .
H17A H 0.3420 0.5769 0.4496 0.033 Uiso 1 1 calc R U . . .
H17B H 0.2985 0.6577 0.4073 0.033 Uiso 1 1 calc R U . . .
C18 C 0.3165(2) 0.4939(3) 0.38235(13) 0.0304(8) Uani 1 1 d . . . . .
H18A H 0.2446 0.4698 0.3912 0.037 Uiso 1 1 calc R U . . .
H18B H 0.3166 0.5147 0.3470 0.037 Uiso 1 1 calc R U . . .
C19 C 0.3943(2) 0.3971(3) 0.39080(12) 0.0243(8) Uani 1 1 d . . . . .
H19A H 0.3747 0.3344 0.3691 0.029 Uiso 1 1 calc R U . . .
H19B H 0.3888 0.3717 0.4255 0.029 Uiso 1 1 calc R U . . .
C20 C 0.5099(2) 0.4312(3) 0.37989(11) 0.0230(7) Uani 1 1 d . . . . .
H20A H 0.5576 0.3693 0.3883 0.028 Uiso 1 1 calc R U . . .
H20B H 0.5180 0.4478 0.3443 0.028 Uiso 1 1 calc R U . . .
N1 N 0.65570(18) 0.5654(2) 0.40407(9) 0.0162(6) Uani 1 1 d . . . . .
N2 N 0.77322(18) 0.4782(2) 0.34147(9) 0.0176(6) Uani 1 1 d . . . . .
N3 N 0.66013(19) 0.6218(2) 0.32020(9) 0.0179(6) Uani 1 1 d . . . . .
H3 H 0.6155 0.6731 0.3295 0.021 Uiso 1 1 calc R U . . .
O1 O 0.67051(16) 0.61064(18) 0.48629(7) 0.0240(5) Uani 1 1 d . . . . .
O2 O 0.76264(16) 0.34422(17) 0.41689(7) 0.0229(5) Uani 1 1 d . . . . .
O3 O 0.91477(16) 0.34223(17) 0.35858(8) 0.0229(5) Uani 1 1 d . . . . .
S1 S 0.83350(6) 0.40616(6) 0.38438(3) 0.0185(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(4) . ?
C1 C6 1.385(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.391(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.401(4) . ?
C4 S1 1.763(3) . ?
C5 C6 1.390(4) . ?
C5 C7 1.503(4) . ?
C6 H6 0.9300 . ?
C7 O1 1.220(3) . ?
C7 N1 1.373(4) . ?
C8 N2 1.316(4) . ?
C8 N3 1.326(4) . ?
C8 N1 1.428(4) . ?
C9 N3 1.470(4) . ?
C9 C14 1.530(4) . ?
C9 C10 1.533(4) . ?
C9 H9 0.9800 . ?
C10 C11 1.530(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.520(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.524(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.526(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N1 1.507(4) . ?
C15 C16 1.522(4) . ?
C15 C20 1.523(4) . ?
C15 H15 0.9800 . ?
C16 C17 1.534(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.521(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.518(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.525(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
N2 S1 1.608(2) . ?
N3 H3 0.8600 . ?
O2 S1 1.436(2) . ?
O3 S1 1.438(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.6(3) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 121.2(3) . . ?
C3 C4 S1 119.6(2) . . ?
C5 C4 S1 119.2(2) . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 C7 117.7(3) . . ?
C4 C5 C7 123.6(3) . . ?
C1 C6 C5 120.6(3) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O1 C7 N1 120.4(3) . . ?
O1 C7 C5 118.9(3) . . ?
N1 C7 C5 120.7(2) . . ?
N2 C8 N3 119.2(3) . . ?
N2 C8 N1 125.8(3) . . ?
N3 C8 N1 114.9(3) . . ?
N3 C9 C14 109.2(2) . . ?
N3 C9 C10 111.0(2) . . ?
C14 C9 C10 111.4(2) . . ?
N3 C9 H9 108.4 . . ?
C14 C9 H9 108.4 . . ?
C10 C9 H9 108.4 . . ?
C11 C10 C9 112.5(3) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 111.2(3) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 110.5(3) . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 111.4(3) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C9 113.0(3) . . ?
C13 C14 H14A 109.0 . . ?
C9 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C9 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
N1 C15 C16 114.0(3) . . ?
N1 C15 C20 111.1(2) . . ?
C16 C15 C20 112.1(2) . . ?
N1 C15 H15 106.4 . . ?
C16 C15 H15 106.4 . . ?
C20 C15 H15 106.4 . . ?
C15 C16 C17 109.9(3) . . ?
C15 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C18 C17 C16 110.2(3) . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C19 C18 C17 110.8(3) . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C18 C19 C20 112.1(3) . . ?
C18 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
C18 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C15 C20 C19 109.8(2) . . ?
C15 C20 H20A 109.7 . . ?
C19 C20 H20A 109.7 . . ?
C15 C20 H20B 109.7 . . ?
C19 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C7 N1 C8 123.8(2) . . ?
C7 N1 C15 118.2(2) . . ?
C8 N1 C15 117.6(2) . . ?
C8 N2 S1 119.3(2) . . ?
C8 N3 C9 122.6(2) . . ?
C8 N3 H3 118.7 . . ?
C9 N3 H3 118.7 . . ?
O2 S1 O3 116.79(13) . . ?
O2 S1 N2 114.04(13) . . ?
O3 S1 N2 105.81(13) . . ?
O2 S1 C4 108.93(13) . . ?
O3 S1 C4 108.05(14) . . ?
N2 S1 C4 102.08(14) . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1494032'
_audit_update_record             
;
2016-07-16 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H19 N3 O3 S'
_chemical_formula_weight         309.38

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.1911(9)
_cell_length_b                   11.3303(9)
_cell_length_c                   25.143(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3188.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    298
_cell_measurement_reflns_used    4142
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      21.04

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.216
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35978
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.620
_diffrn_reflns_theta_max         28.670
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3959
_reflns_number_gt                2255
_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-2013 (Sheldrick, 2013)'
_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+0.7784P] 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         3959
_refine_ls_number_parameters     223
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.025
_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 0.62736(5) 0.39832(4) 0.37325(2) 0.05512(18) Uani 1 1 d . . . . .
O2 O 0.70147(14) 0.32108(12) 0.40416(6) 0.0665(4) Uani 1 1 d . . . . .
O1 O 0.53090(14) 0.34383(13) 0.34503(7) 0.0740(5) Uani 1 1 d . . . . .
O3 O 0.83367(13) 0.56452(15) 0.48557(6) 0.0655(4) Uani 1 1 d . . . . .
N2 N 0.84489(13) 0.53484(13) 0.39702(6) 0.0441(4) Uani 1 1 d . . . . .
N1 N 0.69933(15) 0.47656(14) 0.33061(6) 0.0511(4) Uani 1 1 d . . . . .
N3 N 0.84770(15) 0.60674(14) 0.31133(6) 0.0526(4) Uani 1 1 d . . . . .
H3 H 0.9081 0.6494 0.3228 0.063 Uiso 1 1 calc R U . . .
C8 C 0.79250(17) 0.53765(16) 0.34598(7) 0.0443(4) Uani 1 1 d . . . . .
C5 C 0.57018(18) 0.50960(17) 0.41450(8) 0.0484(5) Uani 1 1 d . . . . .
C6 C 0.65106(17) 0.58280(17) 0.44089(7) 0.0445(5) Uani 1 1 d . . . . .
C7 C 0.78250(17) 0.55982(17) 0.44299(8) 0.0466(5) Uani 1 1 d . . . . .
C10 C 0.97052(18) 0.48956(19) 0.40294(9) 0.0569(6) Uani 1 1 d . . . . .
H10 H 0.9761 0.4543 0.4393 0.068 Uiso 1 1 calc R U . . .
C4 C 0.44774(19) 0.5250(2) 0.42036(9) 0.0612(6) Uani 1 1 d . . . . .
H4 H 0.3934 0.4736 0.4029 0.073 Uiso 1 1 calc R U . . .
C1 C 0.6058(2) 0.67331(19) 0.47201(8) 0.0556(5) Uani 1 1 d . . . . .
H1 H 0.6592 0.7242 0.4904 0.067 Uiso 1 1 calc R U . . .
C3 C 0.4062(2) 0.6154(2) 0.45170(10) 0.0685(7) Uani 1 1 d . . . . .
H3A H 0.3226 0.6261 0.4561 0.082 Uiso 1 1 calc R U . . .
C2 C 0.4841(2) 0.6904(2) 0.47663(9) 0.0661(6) Uani 1 1 d . . . . .
H2 H 0.4543 0.7543 0.4972 0.079 Uiso 1 1 calc R U . . .
C12 C 0.8147(3) 0.6167(3) 0.25516(9) 0.0733(7) Uani 1 1 d . . . . .
C11 C 0.9953(2) 0.3908(2) 0.36397(11) 0.0841(8) Uani 1 1 d . . . . .
H11A H 0.9325 0.3308 0.3668 0.126 Uiso 1 1 calc R U . . .
H11B H 1.0729 0.3549 0.3721 0.126 Uiso 1 1 calc R U . . .
H11C H 0.9967 0.4225 0.3277 0.126 Uiso 1 1 calc R U . . .
C9 C 1.0634(2) 0.5866(2) 0.40049(12) 0.0815(8) Uani 1 1 d . . . . .
H9A H 1.0712 0.6145 0.3637 0.122 Uiso 1 1 calc R U . . .
H9B H 1.1405 0.5560 0.4128 0.122 Uiso 1 1 calc R U . . .
H9C H 1.0386 0.6523 0.4233 0.122 Uiso 1 1 calc R U . . .
C13A C 0.7400(9) 0.7181(9) 0.2475(3) 0.120(3) Uani 0.679(14) 1 d . . P A 1
H13A H 0.6685 0.7111 0.2698 0.180 Uiso 0.679(14) 1 calc R U P A 1
H13B H 0.7162 0.7231 0.2100 0.180 Uiso 0.679(14) 1 calc R U P A 1
H13C H 0.7841 0.7896 0.2574 0.180 Uiso 0.679(14) 1 calc R U P A 1
C14A C 0.9347(7) 0.6291(10) 0.2228(2) 0.124(3) Uani 0.679(14) 1 d . . P A 1
H14A H 0.9782 0.6992 0.2349 0.186 Uiso 0.679(14) 1 calc R U P A 1
H14B H 0.9165 0.6370 0.1848 0.186 Uiso 0.679(14) 1 calc R U P A 1
H14C H 0.9842 0.5588 0.2285 0.186 Uiso 0.679(14) 1 calc R U P A 1
C14B C 0.8802(16) 0.5376(18) 0.2217(4) 0.118(7) Uani 0.321(14) 1 d . . P A 2
H14D H 0.9659 0.5531 0.2254 0.178 Uiso 0.321(14) 1 calc R U P A 2
H14E H 0.8562 0.5495 0.1846 0.178 Uiso 0.321(14) 1 calc R U P A 2
H14F H 0.8632 0.4560 0.2322 0.178 Uiso 0.321(14) 1 calc R U P A 2
C13B C 0.804(3) 0.7441(19) 0.2361(7) 0.184(14) Uani 0.321(14) 1 d . U P A 2
H13D H 0.8803 0.7850 0.2419 0.276 Uiso 0.321(14) 1 calc R U P A 2
H13E H 0.7408 0.7842 0.2561 0.276 Uiso 0.321(14) 1 calc R U P A 2
H13F H 0.7848 0.7451 0.1981 0.276 Uiso 0.321(14) 1 calc R U P A 2
H1A H 0.788(4) 0.542(3) 0.2452(15) 0.066(11) Uiso 0.679(14) 1 d . . P A 1
H1B H 0.719(5) 0.578(5) 0.250(2) 0.033(15) Uiso 0.321(14) 1 d . . P A 2


_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 O1 1.4318(15) . ?
S1 O2 1.4345(15) . ?
S1 N1 1.6074(17) . ?
S1 C5 1.754(2) . ?
O3 C7 1.215(2) . ?
N2 C7 1.380(2) . ?
N2 C8 1.411(2) . ?
N2 C10 1.504(2) . ?
N1 C8 1.310(2) . ?
N3 C8 1.324(2) . ?
N3 C12 1.464(3) . ?
N3 H3 0.8800 . ?
C5 C4 1.389(3) . ?
C5 C6 1.395(3) . ?
C6 C1 1.386(3) . ?
C6 C7 1.495(3) . ?
C10 C11 1.513(3) . ?
C10 C9 1.515(3) . ?
C10 H10 1.0000 . ?
C4 C3 1.374(3) . ?
C4 H4 0.9500 . ?
C1 C2 1.381(3) . ?
C1 H1 0.9500 . ?
C3 C2 1.369(3) . ?
C3 H3A 0.9500 . ?
C2 H2 0.9500 . ?
C12 C14B 1.432(11) . ?
C12 C13A 1.434(9) . ?
C12 C13B 1.525(19) . ?
C12 C14A 1.577(7) . ?
C12 H1A 0.93(4) . ?
C12 H1B 1.16(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 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
O1 S1 O2 116.19(9) . . ?
O1 S1 N1 106.57(10) . . ?
O2 S1 N1 114.09(9) . . ?
O1 S1 C5 109.14(10) . . ?
O2 S1 C5 109.22(10) . . ?
N1 S1 C5 100.42(9) . . ?
C7 N2 C8 123.15(16) . . ?
C7 N2 C10 117.39(16) . . ?
C8 N2 C10 119.09(15) . . ?
C8 N1 S1 119.57(14) . . ?
C8 N3 C12 124.25(19) . . ?
C8 N3 H3 117.9 . . ?
C12 N3 H3 117.9 . . ?
N1 C8 N3 119.32(18) . . ?
N1 C8 N2 125.95(18) . . ?
N3 C8 N2 114.69(17) . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 S1 120.86(17) . . ?
C6 C5 S1 118.16(15) . . ?
C1 C6 C5 118.13(18) . . ?
C1 C6 C7 117.93(18) . . ?
C5 C6 C7 123.47(17) . . ?
O3 C7 N2 120.56(18) . . ?
O3 C7 C6 119.16(18) . . ?
N2 C7 C6 120.27(17) . . ?
N2 C10 C11 111.08(18) . . ?
N2 C10 C9 112.94(18) . . ?
C11 C10 C9 112.6(2) . . ?
N2 C10 H10 106.6 . . ?
C11 C10 H10 106.6 . . ?
C9 C10 H10 106.6 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C2 C1 C6 120.8(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C14B C12 N3 112.9(5) . . ?
C13A C12 N3 109.8(4) . . ?
C14B C12 C13B 116.6(10) . . ?
N3 C12 C13B 113.3(9) . . ?
C13A C12 C14A 110.9(4) . . ?
N3 C12 C14A 106.9(3) . . ?
C13A C12 H1A 120(3) . . ?
N3 C12 H1A 106(2) . . ?
C14A C12 H1A 103(3) . . ?
C14B C12 H1B 100(3) . . ?
N3 C12 H1B 108(3) . . ?
C13B C12 H1B 104(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C13A H13A 109.5 . . ?
C12 C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C12 C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C12 C14A H14A 109.5 . . ?
C12 C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C12 C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C12 C14B H14D 109.5 . . ?
C12 C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C12 C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C12 C13B H13D 109.5 . . ?
C12 C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C12 C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1494033'
_audit_update_record             
;
2016-07-16 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H19 N3 O3 S'
_chemical_formula_weight         309.38

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                   11.537(7)
_cell_length_b                   14.933(9)
_cell_length_c                   9.438(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.304(7)
_cell_angle_gamma                90
_cell_volume                     1504.4(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2641
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      23.75

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.229
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13409
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.908
_diffrn_reflns_theta_max         25.185
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2686
_reflns_number_gt                1804
_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-2013 (Sheldrick, 2013)'
_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)+(0.1077P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2686
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1832
_refine_ls_wR_factor_gt          0.1629
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5829(4) 0.8095(2) 0.7719(4) 0.0536(9) Uani 1 1 d . . . . .
H1 H 0.6122 0.8602 0.7343 0.064 Uiso 1 1 calc R U . . .
C2 C 0.4634(4) 0.8104(2) 0.7741(4) 0.0644(11) Uani 1 1 d . . . . .
H2 H 0.4108 0.8611 0.7364 0.077 Uiso 1 1 calc R U . . .
C3 C 0.4204(4) 0.7374(3) 0.8313(4) 0.0672(11) Uani 1 1 d . . . . .
H3A H 0.3388 0.7385 0.8335 0.081 Uiso 1 1 calc R U . . .
C4 C 0.4966(4) 0.6624(2) 0.8856(4) 0.0569(10) Uani 1 1 d . . . . .
H4 H 0.4676 0.6127 0.9257 0.068 Uiso 1 1 calc R U . . .
C5 C 0.6152(3) 0.6613(2) 0.8804(3) 0.0452(8) Uani 1 1 d . . . . .
C6 C 0.6609(3) 0.73493(19) 0.8244(3) 0.0436(8) Uani 1 1 d . . . . .
C7 C 0.7902(3) 0.74086(19) 0.8296(3) 0.0424(8) Uani 1 1 d . . . . .
C8 C 0.9711(3) 0.6890(2) 0.7749(4) 0.0509(9) Uani 1 1 d . . . . .
H8A H 0.9872 0.7538 0.7711 0.061 Uiso 1 1 calc R U . . .
H8B H 0.9808 0.6604 0.6854 0.061 Uiso 1 1 calc R U . . .
C9 C 1.0656(4) 0.6502(3) 0.9191(5) 0.0894(14) Uani 1 1 d . . . . .
H9A H 1.0567 0.6787 1.0080 0.134 Uiso 1 1 calc R U . . .
H9B H 1.1502 0.6609 0.9217 0.134 Uiso 1 1 calc R U . . .
H9C H 1.0515 0.5856 0.9218 0.134 Uiso 1 1 calc R U . . .
C10 C 0.7846(3) 0.58955(18) 0.7134(3) 0.0392(8) Uani 1 1 d . . . . .
C11 C 0.7679(4) 0.4694(2) 0.5201(4) 0.0485(9) Uani 1 1 d . . . . .
C12 C 0.8174(4) 0.4641(3) 0.3889(5) 0.0797(14) Uani 1 1 d . . . . .
H12A H 0.7789 0.5116 0.3142 0.120 Uiso 1 1 calc R U . . .
H12B H 0.7959 0.4057 0.3383 0.120 Uiso 1 1 calc R U . . .
H12C H 0.9086 0.4715 0.4311 0.120 Uiso 1 1 calc R U . . .
C13 C 0.6319(4) 0.4511(3) 0.4637(5) 0.0742(12) Uani 1 1 d . . . . .
H13A H 0.6029 0.4574 0.5483 0.111 Uiso 1 1 calc R U . . .
H13B H 0.6156 0.3900 0.4232 0.111 Uiso 1 1 calc R U . . .
H13C H 0.5871 0.4937 0.3824 0.111 Uiso 1 1 calc R U . . .
C14 C 0.8421(4) 0.3994(2) 0.6368(5) 0.0784(13) Uani 1 1 d . . . . .
H14A H 0.9313 0.4150 0.6764 0.118 Uiso 1 1 calc R U . . .
H14B H 0.8300 0.3405 0.5876 0.118 Uiso 1 1 calc R U . . .
H14C H 0.8128 0.3978 0.7215 0.118 Uiso 1 1 calc R U . . .
N1 N 0.7278(3) 0.53897(15) 0.7815(3) 0.0429(7) Uani 1 1 d . . . . .
N2 N 0.8407(3) 0.67566(15) 0.7649(3) 0.0408(7) Uani 1 1 d . . . . .
N3 N 0.7970(3) 0.56109(15) 0.5857(3) 0.0434(7) Uani 1 1 d . . . . .
H3 H 0.8249 0.6000 0.5360 0.052 Uiso 1 1 calc R U . . .
O1 O 0.6496(3) 0.49668(15) 0.9799(3) 0.0636(7) Uani 1 1 d . . . . .
O2 O 0.8320(2) 0.59805(16) 1.0557(2) 0.0602(7) Uani 1 1 d . . . . .
O3 O 0.8545(2) 0.80758(13) 0.8871(2) 0.0529(7) Uani 1 1 d . . . . .
S1 S 0.71557(9) 0.56799(5) 0.94068(9) 0.0474(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.388(5) . ?
C1 C6 1.399(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.388(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(4) . ?
C5 S1 1.763(3) . ?
C6 C7 1.477(5) . ?
C7 O3 1.238(4) . ?
C7 N2 1.389(4) . ?
C8 N2 1.484(4) . ?
C8 C9 1.500(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N1 1.316(4) . ?
C10 N3 1.336(3) . ?
C10 N2 1.439(4) . ?
C11 C13 1.479(5) . ?
C11 N3 1.487(4) . ?
C11 C14 1.524(5) . ?
C11 C12 1.550(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N1 S1 1.621(2) . ?
N3 H3 0.8800 . ?
O1 S1 1.437(2) . ?
O2 S1 1.441(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.8(3) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 S1 122.2(3) . . ?
C6 C5 S1 116.4(3) . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 C7 118.0(3) . . ?
C5 C6 C7 123.6(3) . . ?
O3 C7 N2 118.4(3) . . ?
O3 C7 C6 119.5(3) . . ?
N2 C7 C6 122.0(3) . . ?
N2 C8 C9 112.1(3) . . ?
N2 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N2 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 N3 120.1(3) . . ?
N1 C10 N2 126.3(2) . . ?
N3 C10 N2 113.6(2) . . ?
C13 C11 N3 111.2(3) . . ?
C13 C11 C14 111.2(3) . . ?
N3 C11 C14 110.7(3) . . ?
C13 C11 C12 111.4(3) . . ?
N3 C11 C12 106.7(3) . . ?
C14 C11 C12 105.4(3) . . ?
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 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 N1 S1 122.3(2) . . ?
C7 N2 C10 124.4(3) . . ?
C7 N2 C8 117.5(2) . . ?
C10 N2 C8 117.1(2) . . ?
C10 N3 C11 125.7(2) . . ?
C10 N3 H3 117.1 . . ?
C11 N3 H3 117.1 . . ?
O1 S1 O2 118.06(15) . . ?
O1 S1 N1 106.34(13) . . ?
O2 S1 N1 113.41(14) . . ?
O1 S1 C5 108.79(16) . . ?
O2 S1 C5 107.88(15) . . ?
N1 S1 C5 100.94(13) . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.074

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1494034'
_audit_update_record             
;
2016-07-16 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H25 N3 O4 S2'
_chemical_formula_weight         483.59

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   26.324(2)
_cell_length_b                   14.6841(11)
_cell_length_c                   5.8835(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2274.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    5410
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      25.06

_exptl_crystal_description       Rod
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.272
_shelx_estimated_absorpt_T_min   0.854
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31390
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_av_R_equivalents  0.1240
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.704
_diffrn_reflns_theta_max         25.075
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             3896
_reflns_number_gt                3310
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_max     0.928
_reflns_Friedel_fraction_full    0.914

_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-2013 (Sheldrick, 2013)'
_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)+(0.0345P)²+0.9289P] 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_abs_structure_details 
;
 Flack x determined using 1261 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.04(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3896
_refine_ls_number_parameters     302
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0848
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.16007(15) 0.7026(3) 0.5290(7) 0.0135(9) Uani 1 1 d . . . . .
C2 C 0.10387(15) 0.7168(3) 0.5010(8) 0.0213(10) Uani 1 1 d . . . . .
H2A H 0.0876 0.7127 0.6466 0.032 Uiso 1 1 calc R U . . .
H2B H 0.0904 0.6709 0.4018 0.032 Uiso 1 1 calc R U . . .
H2C H 0.0978 0.7759 0.4367 0.032 Uiso 1 1 calc R U . . .
C3 C 0.18515(16) 0.7284(3) 0.7249(7) 0.0164(10) Uani 1 1 d . . . . .
H3 H 0.1665 0.7523 0.8452 0.020 Uiso 1 1 calc R U . . .
C4 C 0.23761(16) 0.7195(3) 0.7474(7) 0.0150(10) Uani 1 1 d . . . . .
H4 H 0.2538 0.7370 0.8809 0.018 Uiso 1 1 calc R U . . .
C5 C 0.26499(15) 0.6845(3) 0.5683(6) 0.0121(10) Uani 1 1 d . . . . .
C6 C 0.24118(16) 0.6571(3) 0.3706(7) 0.0150(10) Uani 1 1 d . . . . .
H6 H 0.2601 0.6333 0.2509 0.018 Uiso 1 1 calc R U . . .
C7 C 0.18890(17) 0.6654(3) 0.3522(7) 0.0188(10) Uani 1 1 d . . . . .
H7 H 0.1727 0.6460 0.2203 0.023 Uiso 1 1 calc R U . . .
C8 C 0.35130(15) 0.7192(2) 0.4540(7) 0.0108(9) Uani 1 1 d . . . . .
C9 C 0.41550(14) 0.6012(3) 0.5109(7) 0.0106(9) Uani 1 1 d . . . . .
C10 C 0.41973(16) 0.4556(3) 0.3345(7) 0.0150(10) Uani 1 1 d . . . . .
H10 H 0.4133 0.4183 0.2100 0.018 Uiso 1 1 calc R U . . .
C11 C 0.40631(15) 0.5463(3) 0.3247(7) 0.0128(9) Uani 1 1 d . . . . .
H11 H 0.3913 0.5701 0.1946 0.015 Uiso 1 1 calc R U . . .
C12 C 0.43748(15) 0.5664(3) 0.7054(7) 0.0118(9) Uani 1 1 d . . . . .
H12 H 0.4428 0.6036 0.8310 0.014 Uiso 1 1 calc R U . . .
C13 C 0.45156(16) 0.4752(3) 0.7116(7) 0.0133(9) Uani 1 1 d . . . . .
H13 H 0.4671 0.4518 0.8412 0.016 Uiso 1 1 calc R U . . .
C14 C 0.44279(15) 0.4185(3) 0.5270(7) 0.0122(9) Uani 1 1 d . . . . .
C15 C 0.45861(17) 0.3197(3) 0.5301(8) 0.0196(10) Uani 1 1 d . . . . .
H15A H 0.4785 0.3079 0.6638 0.029 Uiso 1 1 calc R U . . .
H15B H 0.4785 0.3066 0.3974 0.029 Uiso 1 1 calc R U . . .
H15C H 0.4289 0.2818 0.5313 0.029 Uiso 1 1 calc R U . . .
C16 C 0.44290(15) 0.7590(3) 0.5036(7) 0.0130(9) Uani 1 1 d . . . . .
C17 C 0.43258(14) 0.8592(3) 0.4856(7) 0.0119(9) Uani 1 1 d . . . . .
C18 C 0.45743(16) 0.9148(3) 0.6407(8) 0.0174(9) Uani 1 1 d . . . . .
H18 H 0.4775 0.8889 0.7534 0.021 Uiso 1 1 calc R U . . .
C19 C 0.45259(16) 1.0088(3) 0.6294(8) 0.0216(10) Uani 1 1 d . . . . .
H19 H 0.4687 1.0455 0.7361 0.026 Uiso 1 1 calc R U . . .
C20 C 0.42374(16) 1.0478(3) 0.4590(8) 0.0237(10) Uani 1 1 d . . . . .
H20 H 0.4207 1.1108 0.4508 0.028 Uiso 1 1 calc R U . . .
C21 C 0.39934(17) 0.9936(3) 0.3004(8) 0.0196(10) Uani 1 1 d . . . . .
H21 H 0.3802 1.0200 0.1849 0.024 Uiso 1 1 calc R U . . .
C22 C 0.40361(16) 0.9003(3) 0.3149(7) 0.0135(9) Uani 1 1 d . . . . .
C23 C 0.2949(2) 0.4260(4) 0.6654(9) 0.0431(15) Uani 1 1 d . . . . .
H23A H 0.2703 0.4640 0.5908 0.065 Uiso 1 1 calc R U . . .
H23B H 0.2842 0.3636 0.6568 0.065 Uiso 1 1 calc R U . . .
H23C H 0.3273 0.4326 0.5921 0.065 Uiso 1 1 calc R U . . .
C24 C 0.23462(18) 0.4554(3) 1.0161(9) 0.0340(13) Uani 1 1 d . . . . .
H24A H 0.2295 0.4670 1.1750 0.051 Uiso 1 1 calc R U . . .
H24B H 0.2214 0.3964 0.9784 0.051 Uiso 1 1 calc R U . . .
H24C H 0.2173 0.5011 0.9285 0.051 Uiso 1 1 calc R U . . .
N1 N 0.33367(13) 0.7760(2) 0.3025(6) 0.0117(8) Uani 1 1 d . . . . .
N2 N 0.31885(11) 0.6758(2) 0.5902(5) 0.0113(8) Uani 1 1 d . . . . .
H2 H 0.3308 0.6413 0.6954 0.014 Uiso 1 1 calc R U . . .
N3 N 0.40307(11) 0.6970(2) 0.4926(6) 0.0099(7) Uani 1 1 d . . . . .
O1 O 0.40700(10) 0.76726(18) 0.0214(5) 0.0172(7) Uani 1 1 d . . . . .
O2 O 0.33907(10) 0.88163(19) -0.0186(5) 0.0203(7) Uani 1 1 d . . . . .
O3 O 0.48584(10) 0.73312(19) 0.5338(5) 0.0164(7) Uani 1 1 d . . . . .
O4 O 0.31523(10) 0.55632(18) 0.9571(5) 0.0179(7) Uani 1 1 d . . . . .
S1 S 0.37088(4) 0.82734(7) 0.12617(18) 0.0136(2) Uani 1 1 d . . . . .
S2 S 0.30018(5) 0.45880(8) 0.9541(2) 0.0273(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.381(6) . ?
C1 C7 1.399(6) . ?
C1 C2 1.503(6) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.393(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(5) . ?
C5 N2 1.429(5) . ?
C6 C7 1.386(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.306(5) . ?
C8 N2 1.333(5) . ?
C8 N3 1.420(5) . ?
C9 C12 1.380(5) . ?
C9 C11 1.382(6) . ?
C9 N3 1.449(5) . ?
C10 C11 1.378(6) . ?
C10 C14 1.396(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.390(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.510(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O3 1.206(5) . ?
C16 N3 1.390(5) . ?
C16 C17 1.499(6) . ?
C17 C18 1.389(6) . ?
C17 C22 1.398(6) . ?
C18 C19 1.387(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.377(6) . ?
C21 H21 0.9300 . ?
C22 S1 1.767(4) . ?
C23 S2 1.771(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 S2 1.764(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 S1 1.614(3) . ?
N2 H2 0.8600 . ?
O1 S1 1.436(3) . ?
O2 S1 1.436(3) . ?
O4 S2 1.486(3) . ?

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
C3 C1 C7 117.9(4) . . ?
C3 C1 C2 121.6(4) . . ?
C7 C1 C2 120.4(4) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 C4 121.8(4) . . ?
C1 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 118.8(4) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.1(4) . . ?
C4 C5 N2 118.9(3) . . ?
C6 C5 N2 120.0(3) . . ?
C5 C6 C7 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C1 121.0(4) . . ?
C6 C7 H7 119.5 . . ?
C1 C7 H7 119.5 . . ?
N1 C8 N2 119.2(3) . . ?
N1 C8 N3 126.6(4) . . ?
N2 C8 N3 114.2(3) . . ?
C12 C9 C11 121.0(4) . . ?
C12 C9 N3 121.1(4) . . ?
C11 C9 N3 117.9(3) . . ?
C11 C10 C14 121.5(4) . . ?
C11 C10 H10 119.3 . . ?
C14 C10 H10 119.3 . . ?
C10 C11 C9 119.1(4) . . ?
C10 C11 H11 120.5 . . ?
C9 C11 H11 120.5 . . ?
C9 C12 C13 119.4(4) . . ?
C9 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C10 118.3(4) . . ?
C13 C14 C15 121.4(4) . . ?
C10 C14 C15 120.3(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 N3 120.5(4) . . ?
O3 C16 C17 119.3(4) . . ?
N3 C16 C17 120.2(3) . . ?
C18 C17 C22 118.3(4) . . ?
C18 C17 C16 116.5(4) . . ?
C22 C17 C16 125.0(4) . . ?
C19 C18 C17 120.7(4) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 119.8(4) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.4(4) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 119.5(4) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C17 121.3(4) . . ?
C21 C22 S1 121.6(3) . . ?
C17 C22 S1 117.0(3) . . ?
S2 C23 H23A 109.5 . . ?
S2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
S2 C24 H24A 109.5 . . ?
S2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
S2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C8 N1 S1 121.4(3) . . ?
C8 N2 C5 122.6(3) . . ?
C8 N2 H2 118.7 . . ?
C5 N2 H2 118.7 . . ?
C16 N3 C8 125.5(3) . . ?
C16 N3 C9 117.5(3) . . ?
C8 N3 C9 116.8(3) . . ?
O2 S1 O1 118.20(18) . . ?
O2 S1 N1 106.66(17) . . ?
O1 S1 N1 112.99(17) . . ?
O2 S1 C22 108.68(18) . . ?
O1 S1 C22 108.63(19) . . ?
N1 S1 C22 100.10(19) . . ?
O4 S2 C24 106.6(2) . . ?
O4 S2 C23 107.1(2) . . ?
C24 S2 C23 96.5(3) . . ?

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1494035'
_audit_update_record             
;
2016-07-16 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H29 N3 O3 S'
_chemical_formula_weight         415.54

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                   10.0595(10)
_cell_length_b                   20.175(2)
_cell_length_c                   11.1108(11)
_cell_angle_alpha                90
_cell_angle_beta                 107.837(4)
_cell_angle_gamma                90
_cell_volume                     2146.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9635
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.56

_exptl_crystal_description       Rod
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    0.179
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            65819
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.392
_diffrn_reflns_theta_max         27.639
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4971
_reflns_number_gt                4458
_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-2013 (Sheldrick, 2013)'
_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)+(0.0594P)²+0.8572P] 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         4971
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_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
C1 C 0.0036(2) 0.43878(10) 0.38119(18) 0.0400(5) Uani 1 1 d . . . . .
H1A H 0.0036 0.4863 0.3766 0.060 Uiso 1 1 calc R U . . .
H1B H 0.0106 0.4253 0.4658 0.060 Uiso 1 1 calc R U . . .
H1C H -0.0815 0.4219 0.3237 0.060 Uiso 1 1 calc R U . . .
C2 C 0.12644(16) 0.41183(8) 0.34584(14) 0.0245(3) Uani 1 1 d . . . . .
C3 C 0.15944(15) 0.34482(8) 0.36120(13) 0.0207(3) Uani 1 1 d . . . . .
H3 H 0.1049 0.3168 0.3931 0.025 Uiso 1 1 calc R U . . .
C4 C 0.27201(14) 0.31900(7) 0.32982(12) 0.0168(3) Uani 1 1 d . . . . .
H4 H 0.2918 0.2740 0.3402 0.020 Uiso 1 1 calc R U . . .
C5 C 0.35566(14) 0.35999(7) 0.28286(12) 0.0158(3) Uani 1 1 d . . . . .
C6 C 0.32069(15) 0.42687(7) 0.26372(14) 0.0217(3) Uani 1 1 d . . . . .
H6 H 0.3731 0.4546 0.2291 0.026 Uiso 1 1 calc R U . . .
C7 C 0.20812(17) 0.45218(8) 0.29608(14) 0.0261(3) Uani 1 1 d . . . . .
H7 H 0.1870 0.4970 0.2842 0.031 Uiso 1 1 calc R U . . .
C8 C 0.47773(14) 0.33641(7) 0.24463(13) 0.0167(3) Uani 1 1 d . . . . .
C9 C 0.63920(17) 0.19796(9) 0.18815(16) 0.0307(4) Uani 1 1 d . . . . .
H9A H 0.6312 0.1616 0.2412 0.046 Uiso 1 1 calc R U . . .
H9B H 0.7111 0.1885 0.1503 0.046 Uiso 1 1 calc R U . . .
H9C H 0.5519 0.2042 0.1230 0.046 Uiso 1 1 calc R U . . .
C10 C 0.67626(14) 0.26059(7) 0.26721(13) 0.0186(3) Uani 1 1 d . . . . .
H10 H 0.6955 0.2951 0.2127 0.022 Uiso 1 1 calc R U . . .
C11 C 0.80830(15) 0.25200(9) 0.37828(15) 0.0275(3) Uani 1 1 d . . . . .
H11A H 0.8298 0.2929 0.4244 0.041 Uiso 1 1 calc R U . . .
H11B H 0.8844 0.2400 0.3475 0.041 Uiso 1 1 calc R U . . .
H11C H 0.7941 0.2177 0.4330 0.041 Uiso 1 1 calc R U . . .
C12 C 0.54845(13) 0.25740(6) 0.42485(12) 0.0121(2) Uani 1 1 d . . . . .
C13 C 0.49147(14) 0.15639(6) 0.52290(12) 0.0132(3) Uani 1 1 d . . . . .
H13 H 0.5828 0.1589 0.5877 0.016 Uiso 1 1 calc R U . . .
C14 C 0.46473(16) 0.08481(7) 0.48025(14) 0.0210(3) Uani 1 1 d . . . . .
H14A H 0.3761 0.0816 0.4157 0.031 Uiso 1 1 calc R U . . .
H14B H 0.4639 0.0576 0.5509 0.031 Uiso 1 1 calc R U . . .
H14C H 0.5372 0.0700 0.4471 0.031 Uiso 1 1 calc R U . . .
C15 C 0.38139(14) 0.18199(7) 0.57970(13) 0.0171(3) Uani 1 1 d . . . . .
H15A H 0.3985 0.2280 0.6012 0.026 Uiso 1 1 calc R U . . .
H15B H 0.3859 0.1571 0.6544 0.026 Uiso 1 1 calc R U . . .
H15C H 0.2904 0.1771 0.5193 0.026 Uiso 1 1 calc R U . . .
C16 C 0.55966(13) 0.38856(6) 0.66024(12) 0.0135(3) Uani 1 1 d . . . . .
C17 C 0.45719(14) 0.43507(7) 0.60563(13) 0.0173(3) Uani 1 1 d . . . . .
H17 H 0.4411 0.4481 0.5221 0.021 Uiso 1 1 calc R U . . .
C18 C 0.37932(15) 0.46174(7) 0.67711(14) 0.0197(3) Uani 1 1 d . . . . .
H18 H 0.3102 0.4927 0.6407 0.024 Uiso 1 1 calc R U . . .
C19 C 0.40249(15) 0.44306(7) 0.80263(14) 0.0191(3) Uani 1 1 d . . . . .
C20 C 0.50477(15) 0.39547(7) 0.85513(13) 0.0209(3) Uani 1 1 d . . . . .
H20 H 0.5208 0.3821 0.9385 0.025 Uiso 1 1 calc R U . . .
C21 C 0.58234(15) 0.36813(7) 0.78431(13) 0.0189(3) Uani 1 1 d . . . . .
H21 H 0.6496 0.3361 0.8196 0.023 Uiso 1 1 calc R U . . .
C22 C 0.32108(17) 0.47407(9) 0.88101(16) 0.0293(4) Uani 1 1 d . . . . .
H22A H 0.3447 0.4526 0.9620 0.044 Uiso 1 1 calc R U . . .
H22B H 0.2229 0.4690 0.8387 0.044 Uiso 1 1 calc R U . . .
H22C H 0.3436 0.5204 0.8925 0.044 Uiso 1 1 calc R U . . .
N1 N 0.55701(11) 0.28435(6) 0.30906(10) 0.0139(2) Uani 1 1 d . . . . .
N2 N 0.49669(11) 0.19616(5) 0.41372(10) 0.0125(2) Uani 1 1 d . . . . .
H2 H 0.4650 0.1792 0.3394 0.015 Uiso 1 1 calc R U . . .
N3 N 0.59342(12) 0.28374(5) 0.53708(10) 0.0142(2) Uani 1 1 d . . . . .
O1 O 0.80205(10) 0.34410(5) 0.66391(9) 0.0188(2) Uani 1 1 d . . . . .
O2 O 0.65846(10) 0.39836(5) 0.46963(9) 0.0177(2) Uani 1 1 d . . . . .
O3 O 0.50423(12) 0.36212(6) 0.15515(10) 0.0269(3) Uani 1 1 d . . . . .
S1 S 0.66508(3) 0.35544(2) 0.57445(3) 0.01289(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.508(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.386(2) . ?
C2 C3 1.390(2) . ?
C3 C4 1.385(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3904(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(2) . ?
C5 C8 1.495(2) . ?
C6 C7 1.386(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O3 1.2211(17) . ?
C8 N1 1.3790(18) . ?
C9 C10 1.519(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N1 1.4923(17) . ?
C10 C11 1.521(2) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N3 1.3025(17) . ?
C12 N2 1.3318(17) . ?
C12 N1 1.4233(16) . ?
C13 N2 1.4687(16) . ?
C13 C14 1.5179(18) . ?
C13 C15 1.5229(18) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.3886(19) . ?
C16 C21 1.3890(19) . ?
C16 S1 1.7604(14) . ?
C17 C18 1.384(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.394(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.397(2) . ?
C19 C22 1.502(2) . ?
C20 C21 1.382(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N2 H2 0.8600 . ?
N3 S1 1.6128(11) . ?
O1 S1 1.4490(10) . ?
O2 S1 1.4364(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 118.14(14) . . ?
C7 C2 C1 121.68(15) . . ?
C3 C2 C1 120.18(16) . . ?
C4 C3 C2 121.19(14) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.43(13) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 118.64(13) . . ?
C4 C5 C8 124.17(12) . . ?
C6 C5 C8 117.10(13) . . ?
C7 C6 C5 120.32(14) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C2 121.21(14) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
O3 C8 N1 120.69(13) . . ?
O3 C8 C5 119.96(13) . . ?
N1 C8 C5 119.32(12) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C9 111.67(11) . . ?
N1 C10 C11 111.68(11) . . ?
C9 C10 C11 111.91(13) . . ?
N1 C10 H10 107.1 . . ?
C9 C10 H10 107.1 . . ?
C11 C10 H10 107.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 N2 118.60(11) . . ?
N3 C12 N1 127.59(12) . . ?
N2 C12 N1 113.62(11) . . ?
N2 C13 C14 108.04(11) . . ?
N2 C13 C15 111.81(11) . . ?
C14 C13 C15 111.73(11) . . ?
N2 C13 H13 108.4 . . ?
C14 C13 H13 108.4 . . ?
C15 C13 H13 108.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 120.56(13) . . ?
C17 C16 S1 120.63(10) . . ?
C21 C16 S1 118.80(10) . . ?
C18 C17 C16 119.14(13) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C19 121.24(13) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C20 118.66(13) . . ?
C18 C19 C22 120.91(13) . . ?
C20 C19 C22 120.43(13) . . ?
C21 C20 C19 120.57(13) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C16 119.81(13) . . ?
C20 C21 H21 120.1 . . ?
C16 C21 H21 120.1 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 N1 C12 125.08(11) . . ?
C8 N1 C10 118.37(11) . . ?
C12 N1 C10 115.84(11) . . ?
C12 N2 C13 122.83(11) . . ?
C12 N2 H2 118.6 . . ?
C13 N2 H2 118.6 . . ?
C12 N3 S1 127.53(10) . . ?
O2 S1 O1 116.71(6) . . ?
O2 S1 N3 115.21(6) . . ?
O1 S1 N3 106.93(6) . . ?
O2 S1 C16 108.92(6) . . ?
O1 S1 C16 107.00(6) . . ?
N3 S1 C16 100.60(6) . . ?

_refine_diff_density_max         0.365
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.119

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1494036'
_audit_update_record             
;
2016-07-16 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H37 N3 O3 S'
_chemical_formula_weight         495.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.0370(3)
_cell_length_b                   35.2714(10)
_cell_length_c                   12.5698(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.9780(10)
_cell_angle_gamma                90
_cell_volume                     5297.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      72.23

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             2128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.351
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            89740
_diffrn_reflns_av_unetI/netI     0.1046
_diffrn_reflns_av_R_equivalents  0.1279
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.542
_diffrn_reflns_theta_max         72.591
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             20864
_reflns_number_gt                14988
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.967
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0747P)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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.36(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         20864
_refine_ls_number_parameters     1270
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1531
_refine_ls_wR_factor_gt          0.1357
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9977(7) 0.4475(2) -0.2541(6) 0.0373(19) Uani 1 1 d . . . . .
H1A H 0.9603 0.4405 -0.3231 0.056 Uiso 1 1 calc R U . . .
H1B H 0.9967 0.4265 -0.2057 0.056 Uiso 1 1 calc R U . . .
H1C H 1.0737 0.4543 -0.2606 0.056 Uiso 1 1 calc R U . . .
C2 C 0.9380(6) 0.4810(2) -0.2110(5) 0.0295(17) Uani 1 1 d . . . . .
C3 C 0.8232(6) 0.4786(2) -0.1989(5) 0.0282(17) Uani 1 1 d . . . . .
H3 H 0.7847 0.4561 -0.2146 0.034 Uiso 1 1 calc R U . . .
C4 C 0.7681(6) 0.5093(2) -0.1642(5) 0.0264(16) Uani 1 1 d . . . . .
H4 H 0.6921 0.5076 -0.1577 0.032 Uiso 1 1 calc R U . . .
C5 C 0.8244(6) 0.54283(19) -0.1387(5) 0.0193(14) Uani 1 1 d . . . . .
C6 C 0.9376(6) 0.5457(2) -0.1480(5) 0.0257(16) Uani 1 1 d . . . . .
H6 H 0.9762 0.5681 -0.1302 0.031 Uiso 1 1 calc R U . . .
C7 C 0.9921(6) 0.5147(2) -0.1842(5) 0.0273(16) Uani 1 1 d . . . . .
H7A H 1.0680 0.5166 -0.1907 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6230(6) 0.6729(2) -0.0068(4) 0.0226(15) Uani 1 1 d . . . . .
H8A H 0.6157 0.6556 -0.0672 0.027 Uiso 1 1 calc R U . . .
H8B H 0.6898 0.6880 -0.0097 0.027 Uiso 1 1 calc R U . . .
C9 C 0.5205(6) 0.6986(2) -0.0128(5) 0.0265(16) Uani 1 1 d . . . . .
H9A H 0.4536 0.6832 -0.0152 0.032 Uiso 1 1 calc R U . . .
H9B H 0.5154 0.7135 -0.0782 0.032 Uiso 1 1 calc R U . . .
C10 C 0.5268(6) 0.72537(19) 0.0836(5) 0.0238(15) Uani 1 1 d . . . . .
H10X H 0.5893 0.7427 0.0821 0.029 Uiso 1 1 calc R U . . .
H10Y H 0.4587 0.7402 0.0800 0.029 Uiso 1 1 calc R U . . .
C11 C 0.5419(6) 0.7026(2) 0.1877(5) 0.0258(16) Uani 1 1 d . . . . .
H11I H 0.5499 0.7199 0.2481 0.031 Uiso 1 1 calc R U . . .
H11J H 0.4756 0.6873 0.1923 0.031 Uiso 1 1 calc R U . . .
C12 C 0.6438(6) 0.6770(2) 0.1941(5) 0.0235(15) Uani 1 1 d . . . . .
H12A H 0.6497 0.6622 0.2597 0.028 Uiso 1 1 calc R U . . .
H12B H 0.7111 0.6922 0.1950 0.028 Uiso 1 1 calc R U . . .
C13 C 0.6329(5) 0.65052(19) 0.0976(4) 0.0190(14) Uani 1 1 d . . . . .
H13 H 0.5626 0.6365 0.0983 0.023 Uiso 1 1 calc R U . . .
C14 C 0.8174(5) 0.62727(19) 0.0462(5) 0.0200(14) Uani 1 1 d . . . . .
C15 C 0.9837(6) 0.66762(19) 0.0319(5) 0.0220(15) Uani 1 1 d . . . . .
H15 H 0.9682 0.6632 -0.0455 0.026 Uiso 1 1 calc R U . . .
C16 C 1.0881(6) 0.6458(2) 0.0747(5) 0.0275(16) Uani 1 1 d . . . . .
H16A H 1.1001 0.6480 0.1522 0.033 Uiso 1 1 calc R U . . .
H16B H 1.0775 0.6191 0.0570 0.033 Uiso 1 1 calc R U . . .
C17 C 1.1899(6) 0.6603(2) 0.0283(6) 0.0298(17) Uani 1 1 d . . . . .
H17A H 1.1813 0.6557 -0.0483 0.036 Uiso 1 1 calc R U . . .
H17B H 1.2557 0.6467 0.0601 0.036 Uiso 1 1 calc R U . . .
C18 C 1.2063(6) 0.7029(2) 0.0495(5) 0.0268(17) Uani 1 1 d . . . . .
H18A H 1.2216 0.7074 0.1260 0.032 Uiso 1 1 calc R U . . .
H18B H 1.2699 0.7119 0.0160 0.032 Uiso 1 1 calc R U . . .
C19 C 1.1012(6) 0.7247(2) 0.0042(6) 0.0278(16) Uani 1 1 d . . . . .
H19A H 1.1114 0.7515 0.0204 0.033 Uiso 1 1 calc R U . . .
H19B H 1.0897 0.7219 -0.0731 0.033 Uiso 1 1 calc R U . . .
C21 C 0.9987(6) 0.7102(2) 0.0514(5) 0.0249(16) Uani 1 1 d . . . . .
H21A H 0.9327 0.7235 0.0189 0.030 Uiso 1 1 calc R U . . .
H21B H 1.0070 0.7152 0.1279 0.030 Uiso 1 1 calc R U . . .
C22 C 0.7069(6) 0.5877(2) 0.1551(5) 0.0229(15) Uani 1 1 d . . . . .
C23 C 0.8007(6) 0.5592(2) 0.1642(5) 0.0221(15) Uani 1 1 d . . . . .
C24 C 0.9104(6) 0.5686(2) 0.2040(5) 0.0273(16) Uani 1 1 d . . . . .
H24 H 0.9293 0.5935 0.2231 0.033 Uiso 1 1 calc R U . . .
C25 C 0.9920(7) 0.5399(2) 0.2148(6) 0.0347(19) Uani 1 1 d . . . . .
H25 H 1.0655 0.5461 0.2403 0.042 Uiso 1 1 calc R U . . .
C26 C 0.9655(7) 0.5024(2) 0.1882(5) 0.0318(18) Uani 1 1 d . . . . .
C27 C 1.0540(7) 0.4718(2) 0.2032(6) 0.042(2) Uani 1 1 d . . . . .
H27A H 1.1048 0.4748 0.1506 0.063 Uiso 1 1 calc R U . . .
H27B H 1.0188 0.4474 0.1949 0.063 Uiso 1 1 calc R U . . .
H27C H 1.0944 0.4738 0.2737 0.063 Uiso 1 1 calc R U . . .
C28 C 0.8555(7) 0.4937(2) 0.1509(5) 0.0319(18) Uani 1 1 d . . . . .
H28 H 0.8363 0.4688 0.1336 0.038 Uiso 1 1 calc R U . . .
C29 C 0.7725(6) 0.5219(2) 0.1388(5) 0.0265(16) Uani 1 1 d . . . . .
H29 H 0.6990 0.5156 0.1138 0.032 Uiso 1 1 calc R U . . .
C30 C 0.7760(5) 0.70216(19) 0.6197(5) 0.0205(14) Uani 1 1 d . . . . .
H30 H 0.7959 0.7287 0.6358 0.025 Uiso 1 1 calc R U . . .
C31 C 0.7144(5) 0.7008(2) 0.5055(5) 0.0219(16) Uani 1 1 d . . . . .
H31A H 0.7621 0.7109 0.4555 0.026 Uiso 1 1 calc R U . . .
H31B H 0.6966 0.6747 0.4857 0.026 Uiso 1 1 calc R U . . .
C32 C 0.6065(6) 0.7241(2) 0.4998(5) 0.0234(16) Uani 1 1 d . . . . .
H32A H 0.6252 0.7505 0.5142 0.028 Uiso 1 1 calc R U . . .
H32B H 0.5669 0.7224 0.4280 0.028 Uiso 1 1 calc R U . . .
C33 C 0.5309(6) 0.7102(2) 0.5799(5) 0.0274(16) Uani 1 1 d . . . . .
H33A H 0.5085 0.6842 0.5633 0.033 Uiso 1 1 calc R U . . .
H33B H 0.4639 0.7257 0.5749 0.033 Uiso 1 1 calc R U . . .
C34 C 0.7011(6) 0.6891(2) 0.7013(5) 0.0228(15) Uani 1 1 d . . . . .
H34A H 0.7408 0.6917 0.7728 0.027 Uiso 1 1 calc R U . . .
H34B H 0.6832 0.6625 0.6896 0.027 Uiso 1 1 calc R U . . .
C35 C 0.5920(5) 0.7122(2) 0.6933(5) 0.0215(14) Uani 1 1 d . . . . .
H35A H 0.5443 0.7023 0.7436 0.026 Uiso 1 1 calc R U . . .
H35B H 0.6092 0.7384 0.7119 0.026 Uiso 1 1 calc R U . . .
C36 C 0.9781(5) 0.6956(2) 0.6817(4) 0.0192(14) Uani 1 1 d . . . . .
C37 C 1.0816(5) 0.67114(19) 0.6978(5) 0.0192(14) Uani 1 1 d . . . . .
C38 C 1.0810(6) 0.6337(2) 0.7285(5) 0.0258(16) Uani 1 1 d . . . . .
H38 H 1.0132 0.6217 0.7345 0.031 Uiso 1 1 calc R U . . .
C39 C 1.1805(6) 0.6134(2) 0.7508(6) 0.0322(18) Uani 1 1 d . . . . .
H39 H 1.1784 0.5882 0.7727 0.039 Uiso 1 1 calc R U . . .
C40 C 1.2830(6) 0.6304(2) 0.7407(6) 0.0317(18) Uani 1 1 d . . . . .
C41 C 1.3925(7) 0.6086(3) 0.7672(8) 0.053(3) Uani 1 1 d . . . . .
H41A H 1.4288 0.6061 0.7037 0.079 Uiso 1 1 calc R U . . .
H41B H 1.3771 0.5839 0.7938 0.079 Uiso 1 1 calc R U . . .
H41C H 1.4406 0.6222 0.8208 0.079 Uiso 1 1 calc R U . . .
C42 C 1.1842(6) 0.6886(2) 0.6882(6) 0.0268(16) Uani 1 1 d . . . . .
H42 H 1.1866 0.7140 0.6680 0.032 Uiso 1 1 calc R U . . .
C43 C 1.2809(6) 0.6682(2) 0.7089(6) 0.0353(19) Uani 1 1 d . . . . .
H43 H 1.3484 0.6801 0.7013 0.042 Uiso 1 1 calc R U . . .
C44 C 0.8061(5) 0.58327(19) 0.5270(5) 0.0189(14) Uani 1 1 d . . . . .
H44 H 0.7973 0.5905 0.4512 0.023 Uiso 1 1 calc R U . . .
C45 C 0.9062(6) 0.5559(2) 0.5477(5) 0.0291(17) Uani 1 1 d . . . . .
H45A H 0.9188 0.5495 0.6232 0.035 Uiso 1 1 calc R U . . .
H45B H 0.9732 0.5680 0.5284 0.035 Uiso 1 1 calc R U . . .
C46 C 0.8829(7) 0.5194(2) 0.4809(6) 0.0365(19) Uani 1 1 d . . . . .
H46A H 0.8793 0.5254 0.4053 0.044 Uiso 1 1 calc R U . . .
H46B H 0.9436 0.5015 0.4987 0.044 Uiso 1 1 calc R U . . .
C47 C 0.7734(7) 0.5015(2) 0.5031(6) 0.037(2) Uani 1 1 d . . . . .
H47A H 0.7579 0.4796 0.4572 0.045 Uiso 1 1 calc R U . . .
H47B H 0.7802 0.4930 0.5769 0.045 Uiso 1 1 calc R U . . .
C48 C 0.6772(6) 0.5293(2) 0.4833(5) 0.0295(17) Uani 1 1 d . . . . .
H48A H 0.6089 0.5172 0.4996 0.035 Uiso 1 1 calc R U . . .
H48B H 0.6670 0.5364 0.4081 0.035 Uiso 1 1 calc R U . . .
C49 C 0.6985(6) 0.5648(2) 0.5517(5) 0.0263(16) Uani 1 1 d . . . . .
H49A H 0.6366 0.5824 0.5362 0.032 Uiso 1 1 calc R U . . .
H49B H 0.7044 0.5582 0.6270 0.032 Uiso 1 1 calc R U . . .
C50 C 1.1236(6) 0.6584(2) 0.4035(4) 0.0189(15) Uani 1 1 d . . . . .
C51 C 1.1423(6) 0.6200(2) 0.3905(5) 0.0262(16) Uani 1 1 d . . . . .
H51 H 1.0836 0.6029 0.3921 0.031 Uiso 1 1 calc R U . . .
C52 C 1.2466(6) 0.6069(2) 0.3754(6) 0.0335(18) Uani 1 1 d . . . . .
H52 H 1.2576 0.5810 0.3665 0.040 Uiso 1 1 calc R U . . .
C53 C 1.4504(6) 0.6170(2) 0.3578(6) 0.039(2) Uani 1 1 d . . . . .
H53A H 1.5062 0.6351 0.3851 0.058 Uiso 1 1 calc R U . . .
H53B H 1.4545 0.6129 0.2828 0.058 Uiso 1 1 calc R U . . .
H53C H 1.4634 0.5934 0.3956 0.058 Uiso 1 1 calc R U . . .
C54 C 1.3364(6) 0.6317(2) 0.3730(5) 0.0292(17) Uani 1 1 d . . . . .
C55 C 1.3163(6) 0.6705(2) 0.3854(5) 0.0298(17) Uani 1 1 d . . . . .
H55 H 1.3741 0.6879 0.3830 0.036 Uiso 1 1 calc R U . . .
C56 C 1.2116(6) 0.6830(2) 0.4010(5) 0.0234(15) Uani 1 1 d . . . . .
H56 H 1.1998 0.7088 0.4100 0.028 Uiso 1 1 calc R U . . .
C57 C 0.8839(5) 0.64668(19) 0.5631(5) 0.0197(14) Uani 1 1 d . . . . .
C58 C -0.1958(6) 0.3799(2) 0.4437(7) 0.040(2) Uani 1 1 d . . . . .
H58A H -0.1925 0.3858 0.5185 0.061 Uiso 1 1 calc R U . . .
H58B H -0.2495 0.3600 0.4258 0.061 Uiso 1 1 calc R U . . .
H58C H -0.2177 0.4020 0.4021 0.061 Uiso 1 1 calc R U . . .
C59 C -0.0815(6) 0.3668(2) 0.4193(5) 0.0247(15) Uani 1 1 d . . . . .
C60 C -0.0547(5) 0.3284(2) 0.4166(5) 0.0230(15) Uani 1 1 d . . . . .
H60 H -0.1079 0.3104 0.4297 0.028 Uiso 1 1 calc R U . . .
C61 C 0.0504(5) 0.31646(19) 0.3944(5) 0.0196(14) Uani 1 1 d . . . . .
H61 H 0.0669 0.2908 0.3914 0.024 Uiso 1 1 calc R U . . .
C62 C 0.1292(5) 0.34322(19) 0.3771(4) 0.0175(14) Uani 1 1 d . . . . .
C63 C 0.1061(6) 0.3817(2) 0.3793(5) 0.0261(16) Uani 1 1 d . . . . .
H63 H 0.1599 0.3996 0.3673 0.031 Uiso 1 1 calc R U . . .
C64 C -0.0005(7) 0.3927(2) 0.4002(6) 0.0332(19) Uani 1 1 d . . . . .
H64 H -0.0175 0.4184 0.4012 0.040 Uiso 1 1 calc R U . . .
C65 C 0.3699(5) 0.35642(18) 0.2146(4) 0.0147(13) Uani 1 1 d . . . . .
C66 C 0.2877(5) 0.30503(19) 0.1005(4) 0.0182(14) Uani 1 1 d . . . . .
C67 C 0.1817(5) 0.3276(2) 0.0816(4) 0.0186(14) Uani 1 1 d . . . . .
C68 C 0.0829(5) 0.3102(2) 0.0996(5) 0.0226(15) Uani 1 1 d . . . . .
H68 H 0.0836 0.2854 0.1250 0.027 Uiso 1 1 calc R U . . .
C69 C -0.0181(6) 0.3299(2) 0.0796(5) 0.0284(16) Uani 1 1 d . . . . .
H69 H -0.0841 0.3183 0.0937 0.034 Uiso 1 1 calc R U . . .
C70 C -0.1327(7) 0.3874(3) 0.0141(8) 0.050(2) Uani 1 1 d . . . . .
H70A H -0.1216 0.4139 0.0288 0.074 Uiso 1 1 calc R U . . .
H70B H -0.1857 0.3774 0.0580 0.074 Uiso 1 1 calc R U . . .
H70C H -0.1607 0.3840 -0.0601 0.074 Uiso 1 1 calc R U . . .
C71 C -0.0215(6) 0.3665(2) 0.0389(5) 0.0294(17) Uani 1 1 d . . . . .
C72 C 0.0784(6) 0.3836(2) 0.0198(5) 0.0254(16) Uani 1 1 d . . . . .
H72 H 0.0771 0.4081 -0.0076 0.031 Uiso 1 1 calc R U . . .
C73 C 0.1791(6) 0.3648(2) 0.0408(5) 0.0229(15) Uani 1 1 d . . . . .
H73 H 0.2452 0.3767 0.0281 0.028 Uiso 1 1 calc R U . . .
C74 C 0.4894(5) 0.30216(19) 0.1702(4) 0.0159(13) Uani 1 1 d . . . . .
H74 H 0.4713 0.2752 0.1600 0.019 Uiso 1 1 calc R U . . .
C75 C 0.5662(5) 0.31290(19) 0.0864(4) 0.0180(14) Uani 1 1 d . . . . .
H75A H 0.5279 0.3085 0.0151 0.022 Uiso 1 1 calc R U . . .
H75B H 0.5851 0.3396 0.0929 0.022 Uiso 1 1 calc R U . . .
C76 C 0.6731(5) 0.2890(2) 0.1034(5) 0.0200(14) Uani 1 1 d . . . . .
H76A H 0.6541 0.2625 0.0912 0.024 Uiso 1 1 calc R U . . .
H76B H 0.7224 0.2965 0.0515 0.024 Uiso 1 1 calc R U . . .
C77 C 0.7341(6) 0.2936(2) 0.2151(5) 0.0225(15) Uani 1 1 d . . . . .
H77A H 0.7588 0.3197 0.2259 0.027 Uiso 1 1 calc R U . . .
H77B H 0.7996 0.2774 0.2238 0.027 Uiso 1 1 calc R U . . .
C78 C 0.6563(5) 0.2831(2) 0.2980(5) 0.0221(15) Uani 1 1 d . . . . .
H78A H 0.6375 0.2564 0.2910 0.026 Uiso 1 1 calc R U . . .
H78B H 0.6949 0.2872 0.3694 0.026 Uiso 1 1 calc R U . . .
C79 C 0.5490(5) 0.3065(2) 0.2839(4) 0.0200(14) Uani 1 1 d . . . . .
H79A H 0.5668 0.3330 0.2978 0.024 Uiso 1 1 calc R U . . .
H79B H 0.4999 0.2982 0.3351 0.024 Uiso 1 1 calc R U . . .
C80 C 0.4433(6) 0.42079(19) 0.2480(4) 0.0217(15) Uani 1 1 d . . . . .
H80 H 0.4480 0.4141 0.3241 0.026 Uiso 1 1 calc R U . . .
C81 C 0.5524(6) 0.4399(2) 0.2286(5) 0.0259(17) Uani 1 1 d . . . . .
H81A H 0.6146 0.4228 0.2478 0.031 Uiso 1 1 calc R U . . .
H81B H 0.5504 0.4462 0.1532 0.031 Uiso 1 1 calc R U . . .
C82 C 0.5685(6) 0.4756(2) 0.2955(5) 0.0321(18) Uani 1 1 d . . . . .
H82A H 0.6376 0.4879 0.2824 0.039 Uiso 1 1 calc R U . . .
H82B H 0.5746 0.4690 0.3709 0.039 Uiso 1 1 calc R U . . .
C83 C 0.4709(7) 0.5031(2) 0.2690(6) 0.036(2) Uani 1 1 d . . . . .
H83A H 0.4678 0.5112 0.1950 0.043 Uiso 1 1 calc R U . . .
H83B H 0.4823 0.5254 0.3144 0.043 Uiso 1 1 calc R U . . .
C84 C 0.3601(7) 0.4838(2) 0.2866(6) 0.035(2) Uani 1 1 d . . . . .
H84A H 0.2982 0.5009 0.2649 0.042 Uiso 1 1 calc R U . . .
H84B H 0.3601 0.4782 0.3622 0.042 Uiso 1 1 calc R U . . .
C85 C 0.3447(6) 0.4469(2) 0.2213(5) 0.0288(17) Uani 1 1 d . . . . .
H85A H 0.2769 0.4342 0.2366 0.035 Uiso 1 1 calc R U . . .
H85B H 0.3366 0.4528 0.1454 0.035 Uiso 1 1 calc R U . . .
C86 C 0.2384(7) 0.5521(2) 1.0227(6) 0.038(2) Uani 1 1 d . . . . .
H86A H 0.1601 0.5462 1.0186 0.058 Uiso 1 1 calc R U . . .
H86B H 0.2483 0.5742 0.9802 0.058 Uiso 1 1 calc R U . . .
H86C H 0.2676 0.5570 1.0959 0.058 Uiso 1 1 calc R U . . .
C87 C 0.3000(7) 0.5190(2) 0.9808(5) 0.0285(17) Uani 1 1 d . . . . .
C88 C 0.4129(7) 0.5217(2) 0.9726(5) 0.0308(18) Uani 1 1 d . . . . .
H88 H 0.4500 0.5444 0.9896 0.037 Uiso 1 1 calc R U . . .
C89 C 0.4723(6) 0.4906(2) 0.9391(5) 0.0267(16) Uani 1 1 d . . . . .
H89 H 0.5488 0.4924 0.9349 0.032 Uiso 1 1 calc R U . . .
C90 C 0.4152(6) 0.45715(18) 0.9121(5) 0.0191(14) Uani 1 1 d . . . . .
C91 C 0.3006(6) 0.45413(19) 0.9156(5) 0.0229(15) Uani 1 1 d . . . . .
H91 H 0.2625 0.4319 0.8946 0.027 Uiso 1 1 calc R U . . .
C92 C 0.2443(6) 0.4852(2) 0.9514(5) 0.0281(17) Uani 1 1 d . . . . .
H92 H 0.1679 0.4834 0.9558 0.034 Uiso 1 1 calc R U . . .
C93 C 0.1906(7) 0.5268(2) 0.5647(7) 0.044(2) Uani 1 1 d . . . . .
H93A H 0.2250 0.5512 0.5759 0.066 Uiso 1 1 calc R U . . .
H93B H 0.1383 0.5230 0.6156 0.066 Uiso 1 1 calc R U . . .
H93C H 0.1520 0.5254 0.4933 0.066 Uiso 1 1 calc R U . . .
C94 C 0.2799(7) 0.4963(2) 0.5793(5) 0.0313(18) Uani 1 1 d . . . . .
C95 C 0.2537(6) 0.4588(2) 0.5534(5) 0.0280(16) Uani 1 1 d . . . . .
H95 H 0.1807 0.4523 0.5267 0.034 Uiso 1 1 calc R U . . .
C96 C 0.3347(6) 0.4310(2) 0.5668(5) 0.0242(15) Uani 1 1 d . . . . .
H96 H 0.3154 0.4060 0.5492 0.029 Uiso 1 1 calc R U . . .
C97 C 0.4444(6) 0.43961(19) 0.6063(5) 0.0210(15) Uani 1 1 d . . . . .
C98 C 0.4724(6) 0.4773(2) 0.6311(5) 0.0285(17) Uani 1 1 d . . . . .
H98 H 0.5458 0.4836 0.6569 0.034 Uiso 1 1 calc R U . . .
C99 C 0.3917(7) 0.5052(2) 0.6176(6) 0.0308(18) Uani 1 1 d . . . . .
H99 H 0.4114 0.5302 0.6341 0.037 Uiso 1 1 calc R U . . .
C100 C 0.5375(6) 0.41097(19) 0.6199(5) 0.0202(14) Uani 1 1 d . . . . .
C101 C 0.4242(5) 0.37220(18) 0.7286(4) 0.0160(13) Uani 1 1 d . . . . .
C102 C 0.6211(6) 0.3300(2) 0.7932(5) 0.0260(17) Uani 1 1 d . . . . .
H10I H 0.5535 0.3163 0.8040 0.031 Uiso 1 1 calc R U . . .
H10J H 0.6331 0.3495 0.8476 0.031 Uiso 1 1 calc R U . . .
C103 C 0.6074(5) 0.34807(19) 0.6825(5) 0.0179(14) Uani 1 1 d . . . . .
H103 H 0.6775 0.3614 0.6751 0.021 Uiso 1 1 calc R U . . .
C104 C 0.5935(6) 0.3179(2) 0.5959(5) 0.0266(16) Uani 1 1 d . . . . .
H10G H 0.5875 0.3299 0.5259 0.032 Uiso 1 1 calc R U . . .
H10H H 0.5250 0.3038 0.6007 0.032 Uiso 1 1 calc R U . . .
C105 C 0.6926(6) 0.2908(2) 0.6078(5) 0.0264(16) Uani 1 1 d . . . . .
H10E H 0.6797 0.2708 0.5546 0.032 Uiso 1 1 calc R U . . .
H10F H 0.7596 0.3044 0.5945 0.032 Uiso 1 1 calc R U . . .
C106 C 0.7108(6) 0.2732(2) 0.7189(5) 0.0256(16) Uani 1 1 d . . . . .
H10C H 0.6484 0.2566 0.7283 0.031 Uiso 1 1 calc R U . . .
H10D H 0.7783 0.2579 0.7254 0.031 Uiso 1 1 calc R U . . .
C107 C 0.7211(6) 0.3026(2) 0.8041(5) 0.0311(18) Uani 1 1 d . . . . .
H10K H 0.7894 0.3169 0.8006 0.037 Uiso 1 1 calc R U . . .
H10L H 0.7266 0.2903 0.8735 0.037 Uiso 1 1 calc R U . . .
C108 C 0.2471(6) 0.28930(19) 0.7219(5) 0.0229(15) Uani 1 1 d . . . . .
H10A H 0.3150 0.2769 0.7537 0.027 Uiso 1 1 calc R U . . .
H10B H 0.2382 0.2841 0.6455 0.027 Uiso 1 1 calc R U . . .
C109 C 0.2577(5) 0.33182(19) 0.7402(4) 0.0182(14) Uani 1 1 d . . . . .
H109 H 0.2723 0.3366 0.8175 0.022 Uiso 1 1 calc R U . . .
C110 C 0.1465(6) 0.2731(2) 0.7712(5) 0.0261(16) Uani 1 1 d . . . . .
H11G H 0.1393 0.2463 0.7553 0.031 Uiso 1 1 calc R U . . .
H11H H 0.1586 0.2761 0.8485 0.031 Uiso 1 1 calc R U . . .
C111 C 0.0389(6) 0.2935(2) 0.7266(6) 0.0282(18) Uani 1 1 d . . . . .
H11A H 0.0225 0.2882 0.6506 0.034 Uiso 1 1 calc R U . . .
H11B H -0.0228 0.2841 0.7620 0.034 Uiso 1 1 calc R U . . .
C112 C 0.1504(6) 0.3525(2) 0.6960(5) 0.0242(15) Uani 1 1 d . . . . .
H11C H 0.1392 0.3502 0.6186 0.029 Uiso 1 1 calc R U . . .
H11D H 0.1576 0.3792 0.7137 0.029 Uiso 1 1 calc R U . . .
C113 C 0.0489(6) 0.3360(2) 0.7430(6) 0.0321(18) Uani 1 1 d . . . . .
H11E H 0.0556 0.3415 0.8191 0.038 Uiso 1 1 calc R U . . .
H11F H -0.0186 0.3482 0.7092 0.038 Uiso 1 1 calc R U . . .
N1 N 0.8342(5) 0.60898(16) -0.0405(4) 0.0211(12) Uani 1 1 d . . . . .
N2 N 0.8870(5) 0.65472(15) 0.0831(4) 0.0202(12) Uani 1 1 d . . . . .
H2 H 0.8745 0.6658 0.1415 0.024 Uiso 1 1 calc R U . . .
N3 N 0.7252(4) 0.62180(16) 0.1070(4) 0.0180(12) Uani 1 1 d . . . . .
N4 N 0.9349(5) 0.64339(16) 0.4770(4) 0.0204(12) Uani 1 1 d . . . . .
N5 N 0.8253(4) 0.61781(15) 0.5923(4) 0.0181(12) Uani 1 1 d . . . . .
H5 H 0.7971 0.6192 0.6519 0.022 Uiso 1 1 calc R U . . .
N6 N 0.8820(4) 0.67988(16) 0.6284(4) 0.0167(11) Uani 1 1 d . . . . .
N7 N 0.4288(4) 0.38593(16) 0.1854(4) 0.0176(12) Uani 1 1 d . . . . .
H7 H 0.4594 0.3843 0.1272 0.021 Uiso 1 1 calc R U . . .
N8 N 0.3145(4) 0.36054(15) 0.2969(4) 0.0166(11) Uani 1 1 d . . . . .
N9 N 0.3810(4) 0.32343(15) 0.1534(4) 0.0149(11) Uani 1 1 d . . . . .
N10 N 0.5166(4) 0.37698(15) 0.6697(4) 0.0158(11) Uani 1 1 d . . . . .
N11 N 0.3529(4) 0.34572(15) 0.6894(4) 0.0175(12) Uani 1 1 d . . . . .
H11 H 0.3633 0.3358 0.6288 0.021 Uiso 1 1 calc R U . . .
N12 N 0.4064(4) 0.39095(16) 0.8152(4) 0.0184(12) Uani 1 1 d . . . . .
O1 O 0.6191(4) 0.58093(15) 0.1910(4) 0.0316(12) Uani 1 1 d . . . . .
O2 O 0.7150(4) 0.60241(14) -0.2133(3) 0.0263(12) Uani 1 1 d . . . . .
O3 O 0.6492(4) 0.57062(14) -0.0608(3) 0.0249(11) Uani 1 1 d . . . . .
O4 O 0.9289(4) 0.67712(14) 0.3077(3) 0.0243(10) Uani 1 1 d . . . . .
O5 O 1.0011(4) 0.71282(14) 0.4668(3) 0.0233(11) Uani 1 1 d . . . . .
O6 O 0.9791(4) 0.72716(14) 0.7201(3) 0.0266(11) Uani 1 1 d . . . . .
O7 O 0.2939(4) 0.27300(13) 0.0650(3) 0.0241(11) Uani 1 1 d . . . . .
O8 O 0.3286(4) 0.32668(14) 0.4681(3) 0.0228(10) Uani 1 1 d . . . . .
O9 O 0.2555(4) 0.29057(13) 0.3093(3) 0.0198(10) Uani 1 1 d . . . . .
O10 O 0.6252(4) 0.41700(15) 0.5850(4) 0.0302(11) Uani 1 1 d . . . . .
O11 O 0.5256(4) 0.39825(13) 0.9871(3) 0.0242(11) Uani 1 1 d . . . . .
O12 O 0.5902(4) 0.42980(13) 0.8346(3) 0.0217(10) Uani 1 1 d . . . . .
S1 S 0.74327(14) 0.58309(5) -0.11167(11) 0.0199(4) Uani 1 1 d . . . . .
S2 S 0.98906(13) 0.67679(5) 0.41376(11) 0.0186(3) Uani 1 1 d . . . . .
S3 S 0.26528(13) 0.32659(4) 0.36229(10) 0.0155(3) Uani 1 1 d . . . . .
S4 S 0.49689(13) 0.41710(5) 0.88572(11) 0.0177(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.515(10) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.378(10) . ?
C2 C3 1.411(10) . ?
C3 C4 1.369(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(9) . ?
C5 S1 1.780(7) . ?
C6 C7 1.380(10) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C13 1.523(8) . ?
C8 C9 1.526(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.530(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.527(8) . ?
C10 H10X 0.9700 . ?
C10 H10Y 0.9700 . ?
C11 C12 1.519(9) . ?
C11 H11I 0.9700 . ?
C11 H11J 0.9700 . ?
C12 C13 1.523(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N3 1.498(8) . ?
C13 H13 0.9800 . ?
C14 N1 1.303(8) . ?
C14 N2 1.326(8) . ?
C14 N3 1.434(8) . ?
C15 N2 1.470(8) . ?
C15 C16 1.516(9) . ?
C15 C21 1.529(9) . ?
C15 H15 0.9800 . ?
C16 C17 1.510(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.535(9) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.529(10) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C21 1.521(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 O1 1.222(8) . ?
C22 N3 1.377(8) . ?
C22 C23 1.505(9) . ?
C23 C29 1.386(10) . ?
C23 C24 1.395(10) . ?
C24 C25 1.408(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.389(11) . ?
C25 H25 0.9300 . ?
C26 C28 1.384(11) . ?
C26 C27 1.513(10) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.405(10) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 N6 1.492(8) . ?
C30 C34 1.517(8) . ?
C30 C31 1.534(8) . ?
C30 H30 0.9800 . ?
C31 C32 1.530(9) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.519(9) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C35 1.525(9) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.539(9) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 O6 1.213(8) . ?
C36 N6 1.381(8) . ?
C36 C37 1.509(9) . ?
C37 C38 1.378(9) . ?
C37 C42 1.398(9) . ?
C38 C39 1.394(10) . ?
C38 H38 0.9300 . ?
C39 C40 1.391(10) . ?
C39 H39 0.9300 . ?
C40 C43 1.392(11) . ?
C40 C41 1.528(10) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 C43 1.367(10) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C44 N5 1.471(8) . ?
C44 C49 1.515(9) . ?
C44 C45 1.542(9) . ?
C44 H44 0.9800 . ?
C45 C46 1.543(10) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 C47 1.516(11) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C47 C48 1.515(11) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 C49 1.523(9) . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 C56 1.373(9) . ?
C50 C51 1.386(10) . ?
C50 S2 1.764(7) . ?
C51 C52 1.372(10) . ?
C51 H51 0.9300 . ?
C52 C54 1.395(10) . ?
C52 H52 0.9300 . ?
C53 C54 1.501(10) . ?
C53 H53A 0.9600 . ?
C53 H53B 0.9600 . ?
C53 H53C 0.9600 . ?
C54 C55 1.402(10) . ?
C55 C56 1.372(10) . ?
C55 H55 0.9300 . ?
C56 H56 0.9300 . ?
C57 N4 1.313(8) . ?
C57 N5 1.316(8) . ?
C57 N6 1.432(8) . ?
C58 C59 1.517(10) . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C59 C64 1.378(10) . ?
C59 C60 1.394(10) . ?
C60 C61 1.393(9) . ?
C60 H60 0.9300 . ?
C61 C62 1.374(9) . ?
C61 H61 0.9300 . ?
C62 C63 1.385(9) . ?
C62 S3 1.771(6) . ?
C63 C64 1.397(10) . ?
C63 H63 0.9300 . ?
C64 H64 0.9300 . ?
C65 N8 1.304(7) . ?
C65 N7 1.336(8) . ?
C65 N9 1.410(7) . ?
C66 O7 1.221(8) . ?
C66 N9 1.394(8) . ?
C66 C67 1.498(9) . ?
C67 C68 1.383(9) . ?
C67 C73 1.407(9) . ?
C68 C69 1.396(9) . ?
C68 H68 0.9300 . ?
C69 C71 1.388(10) . ?
C69 H69 0.9300 . ?
C70 C71 1.526(10) . ?
C70 H70A 0.9600 . ?
C70 H70B 0.9600 . ?
C70 H70C 0.9600 . ?
C71 C72 1.392(10) . ?
C72 C73 1.380(9) . ?
C72 H72 0.9300 . ?
C73 H73 0.9300 . ?
C74 N9 1.497(8) . ?
C74 C79 1.527(8) . ?
C74 C75 1.531(8) . ?
C74 H74 0.9800 . ?
C75 C76 1.531(9) . ?
C75 H75A 0.9700 . ?
C75 H75B 0.9700 . ?
C76 C77 1.512(8) . ?
C76 H76A 0.9700 . ?
C76 H76B 0.9700 . ?
C77 C78 1.528(8) . ?
C77 H77A 0.9700 . ?
C77 H77B 0.9700 . ?
C78 C79 1.526(9) . ?
C78 H78A 0.9700 . ?
C78 H78B 0.9700 . ?
C79 H79A 0.9700 . ?
C79 H79B 0.9700 . ?
C80 N7 1.459(8) . ?
C80 C85 1.507(10) . ?
C80 C81 1.523(9) . ?
C80 H80 0.9800 . ?
C81 C82 1.514(9) . ?
C81 H81A 0.9700 . ?
C81 H81B 0.9700 . ?
C82 C83 1.528(11) . ?
C82 H82A 0.9700 . ?
C82 H82B 0.9700 . ?
C83 C84 1.537(11) . ?
C83 H83A 0.9700 . ?
C83 H83B 0.9700 . ?
C84 C85 1.540(9) . ?
C84 H84A 0.9700 . ?
C84 H84B 0.9700 . ?
C85 H85A 0.9700 . ?
C85 H85B 0.9700 . ?
C86 C87 1.514(10) . ?
C86 H86A 0.9600 . ?
C86 H86B 0.9600 . ?
C86 H86C 0.9600 . ?
C87 C88 1.378(10) . ?
C87 C92 1.395(10) . ?
C88 C89 1.402(10) . ?
C88 H88 0.9300 . ?
C89 C90 1.388(9) . ?
C89 H89 0.9300 . ?
C90 C91 1.389(9) . ?
C90 S4 1.775(7) . ?
C91 C92 1.393(10) . ?
C91 H91 0.9300 . ?
C92 H92 0.9300 . ?
C93 C94 1.514(10) . ?
C93 H93A 0.9600 . ?
C93 H93B 0.9600 . ?
C93 H93C 0.9600 . ?
C94 C95 1.390(11) . ?
C94 C99 1.409(11) . ?
C95 C96 1.378(10) . ?
C95 H95 0.9300 . ?
C96 C97 1.387(9) . ?
C96 H96 0.9300 . ?
C97 C98 1.397(10) . ?
C97 C100 1.503(9) . ?
C98 C99 1.378(11) . ?
C98 H98 0.9300 . ?
C99 H99 0.9300 . ?
C100 O10 1.210(8) . ?
C100 N10 1.390(8) . ?
C101 N12 1.313(7) . ?
C101 N11 1.323(8) . ?
C101 N10 1.419(8) . ?
C102 C103 1.522(8) . ?
C102 C107 1.537(9) . ?
C102 H10I 0.9700 . ?
C102 H10J 0.9700 . ?
C103 N10 1.489(8) . ?
C103 C104 1.517(9) . ?
C103 H103 0.9800 . ?
C104 C105 1.522(9) . ?
C104 H10G 0.9700 . ?
C104 H10H 0.9700 . ?
C105 C106 1.519(8) . ?
C105 H10E 0.9700 . ?
C105 H10F 0.9700 . ?
C106 C107 1.484(9) . ?
C106 H10C 0.9700 . ?
C106 H10D 0.9700 . ?
C107 H10K 0.9700 . ?
C107 H10L 0.9700 . ?
C108 C109 1.520(9) . ?
C108 C110 1.536(9) . ?
C108 H10A 0.9700 . ?
C108 H10B 0.9700 . ?
C109 N11 1.462(7) . ?
C109 C112 1.528(9) . ?
C109 H109 0.9800 . ?
C110 C111 1.528(10) . ?
C110 H11G 0.9700 . ?
C110 H11H 0.9700 . ?
C111 C113 1.515(10) . ?
C111 H11A 0.9700 . ?
C111 H11B 0.9700 . ?
C112 C113 1.534(9) . ?
C112 H11C 0.9700 . ?
C112 H11D 0.9700 . ?
C113 H11E 0.9700 . ?
C113 H11F 0.9700 . ?
N1 S1 1.611(5) . ?
N2 H2 0.8600 . ?
N4 S2 1.603(6) . ?
N5 H5 0.8600 . ?
N7 H7 0.8600 . ?
N8 S3 1.606(5) . ?
N11 H11 0.8600 . ?
N12 S4 1.609(5) . ?
O2 S1 1.451(5) . ?
O3 S1 1.435(5) . ?
O4 S2 1.437(4) . ?
O5 S2 1.434(5) . ?
O8 S3 1.450(4) . ?
O9 S3 1.433(5) . ?
O11 S4 1.442(4) . ?
O12 S4 1.432(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 117.6(7) . . ?
C7 C2 C1 122.0(7) . . ?
C3 C2 C1 120.4(7) . . ?
C4 C3 C2 120.5(7) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.5(7) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.2(6) . . ?
C4 C5 S1 117.5(5) . . ?
C6 C5 S1 121.8(5) . . ?
C7 C6 C5 118.8(7) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C2 C7 C6 122.4(7) . . ?
C2 C7 H7A 118.8 . . ?
C6 C7 H7A 118.8 . . ?
C13 C8 C9 109.2(5) . . ?
C13 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
C13 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C8 C9 C10 111.4(5) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 110.2(6) . . ?
C11 C10 H10X 109.6 . . ?
C9 C10 H10X 109.6 . . ?
C11 C10 H10Y 109.6 . . ?
C9 C10 H10Y 109.6 . . ?
H10X C10 H10Y 108.1 . . ?
C12 C11 C10 111.7(5) . . ?
C12 C11 H11I 109.3 . . ?
C10 C11 H11I 109.3 . . ?
C12 C11 H11J 109.3 . . ?
C10 C11 H11J 109.3 . . ?
H11I C11 H11J 107.9 . . ?
C11 C12 C13 109.3(5) . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
N3 C13 C8 113.4(5) . . ?
N3 C13 C12 111.1(5) . . ?
C8 C13 C12 111.0(6) . . ?
N3 C13 H13 107.0 . . ?
C8 C13 H13 107.0 . . ?
C12 C13 H13 107.0 . . ?
N1 C14 N2 119.9(6) . . ?
N1 C14 N3 126.0(6) . . ?
N2 C14 N3 114.1(5) . . ?
N2 C15 C16 110.7(5) . . ?
N2 C15 C21 108.6(5) . . ?
C16 C15 C21 111.4(6) . . ?
N2 C15 H15 108.7 . . ?
C16 C15 H15 108.7 . . ?
C21 C15 H15 108.7 . . ?
C17 C16 C15 111.5(6) . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 C18 111.1(6) . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C17 110.1(6) . . ?
C19 C18 H18A 109.6 . . ?
C17 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.2 . . ?
C21 C19 C18 111.1(6) . . ?
C21 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
C21 C19 H19B 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C19 C21 C15 110.7(6) . . ?
C19 C21 H21A 109.5 . . ?
C15 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C15 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
O1 C22 N3 121.6(6) . . ?
O1 C22 C23 121.1(6) . . ?
N3 C22 C23 117.3(6) . . ?
C29 C23 C24 120.3(7) . . ?
C29 C23 C22 117.1(6) . . ?
C24 C23 C22 122.5(6) . . ?
C23 C24 C25 118.8(7) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
C26 C25 C24 121.7(8) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C28 C26 C25 118.3(7) . . ?
C28 C26 C27 120.9(8) . . ?
C25 C26 C27 120.7(8) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 C29 121.2(7) . . ?
C26 C28 H28 119.4 . . ?
C29 C28 H28 119.4 . . ?
C23 C29 C28 119.7(7) . . ?
C23 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
N6 C30 C34 111.3(5) . . ?
N6 C30 C31 111.3(5) . . ?
C34 C30 C31 111.3(6) . . ?
N6 C30 H30 107.6 . . ?
C34 C30 H30 107.6 . . ?
C31 C30 H30 107.6 . . ?
C32 C31 C30 109.8(5) . . ?
C32 C31 H31A 109.7 . . ?
C30 C31 H31A 109.7 . . ?
C32 C31 H31B 109.7 . . ?
C30 C31 H31B 109.7 . . ?
H31A C31 H31B 108.2 . . ?
C33 C32 C31 111.6(6) . . ?
C33 C32 H32A 109.3 . . ?
C31 C32 H32A 109.3 . . ?
C33 C32 H32B 109.3 . . ?
C31 C32 H32B 109.3 . . ?
H32A C32 H32B 108.0 . . ?
C32 C33 C35 110.1(6) . . ?
C32 C33 H33A 109.6 . . ?
C35 C33 H33A 109.6 . . ?
C32 C33 H33B 109.6 . . ?
C35 C33 H33B 109.6 . . ?
H33A C33 H33B 108.1 . . ?
C30 C34 C35 111.5(5) . . ?
C30 C34 H34A 109.3 . . ?
C35 C34 H34A 109.3 . . ?
C30 C34 H34B 109.3 . . ?
C35 C34 H34B 109.3 . . ?
H34A C34 H34B 108.0 . . ?
C33 C35 C34 110.3(5) . . ?
C33 C35 H35A 109.6 . . ?
C34 C35 H35A 109.6 . . ?
C33 C35 H35B 109.6 . . ?
C34 C35 H35B 109.6 . . ?
H35A C35 H35B 108.1 . . ?
O6 C36 N6 122.0(6) . . ?
O6 C36 C37 120.2(6) . . ?
N6 C36 C37 117.7(6) . . ?
C38 C37 C42 118.8(6) . . ?
C38 C37 C36 123.6(6) . . ?
C42 C37 C36 117.4(6) . . ?
C37 C38 C39 121.0(7) . . ?
C37 C38 H38 119.5 . . ?
C39 C38 H38 119.5 . . ?
C40 C39 C38 120.7(7) . . ?
C40 C39 H39 119.7 . . ?
C38 C39 H39 119.7 . . ?
C39 C40 C43 117.0(7) . . ?
C39 C40 C41 121.0(8) . . ?
C43 C40 C41 121.9(8) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C43 C42 C37 119.4(7) . . ?
C43 C42 H42 120.3 . . ?
C37 C42 H42 120.3 . . ?
C42 C43 C40 123.0(7) . . ?
C42 C43 H43 118.5 . . ?
C40 C43 H43 118.5 . . ?
N5 C44 C49 108.7(5) . . ?
N5 C44 C45 111.0(5) . . ?
C49 C44 C45 111.5(6) . . ?
N5 C44 H44 108.5 . . ?
C49 C44 H44 108.5 . . ?
C45 C44 H44 108.5 . . ?
C44 C45 C46 110.1(6) . . ?
C44 C45 H45A 109.6 . . ?
C46 C45 H45A 109.6 . . ?
C44 C45 H45B 109.6 . . ?
C46 C45 H45B 109.6 . . ?
H45A C45 H45B 108.1 . . ?
C47 C46 C45 110.6(6) . . ?
C47 C46 H46A 109.5 . . ?
C45 C46 H46A 109.5 . . ?
C47 C46 H46B 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 108.1 . . ?
C48 C47 C46 111.4(7) . . ?
C48 C47 H47A 109.4 . . ?
C46 C47 H47A 109.4 . . ?
C48 C47 H47B 109.4 . . ?
C46 C47 H47B 109.4 . . ?
H47A C47 H47B 108.0 . . ?
C47 C48 C49 111.5(6) . . ?
C47 C48 H48A 109.3 . . ?
C49 C48 H48A 109.3 . . ?
C47 C48 H48B 109.3 . . ?
C49 C48 H48B 109.3 . . ?
H48A C48 H48B 108.0 . . ?
C44 C49 C48 109.0(6) . . ?
C44 C49 H49A 109.9 . . ?
C48 C49 H49A 109.9 . . ?
C44 C49 H49B 109.9 . . ?
C48 C49 H49B 109.9 . . ?
H49A C49 H49B 108.3 . . ?
C56 C50 C51 118.7(6) . . ?
C56 C50 S2 119.1(6) . . ?
C51 C50 S2 122.1(6) . . ?
C52 C51 C50 120.6(7) . . ?
C52 C51 H51 119.7 . . ?
C50 C51 H51 119.7 . . ?
C51 C52 C54 121.1(8) . . ?
C51 C52 H52 119.5 . . ?
C54 C52 H52 119.5 . . ?
C54 C53 H53A 109.5 . . ?
C54 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C54 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C52 C54 C55 117.8(7) . . ?
C52 C54 C53 120.5(7) . . ?
C55 C54 C53 121.7(7) . . ?
C56 C55 C54 120.3(7) . . ?
C56 C55 H55 119.9 . . ?
C54 C55 H55 119.9 . . ?
C55 C56 C50 121.6(7) . . ?
C55 C56 H56 119.2 . . ?
C50 C56 H56 119.2 . . ?
N4 C57 N5 118.8(6) . . ?
N4 C57 N6 125.9(6) . . ?
N5 C57 N6 115.2(5) . . ?
C59 C58 H58A 109.5 . . ?
C59 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C59 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C64 C59 C60 118.0(7) . . ?
C64 C59 C58 120.8(7) . . ?
C60 C59 C58 121.2(7) . . ?
C61 C60 C59 121.1(6) . . ?
C61 C60 H60 119.4 . . ?
C59 C60 H60 119.4 . . ?
C62 C61 C60 119.0(6) . . ?
C62 C61 H61 120.5 . . ?
C60 C61 H61 120.5 . . ?
C61 C62 C63 121.7(6) . . ?
C61 C62 S3 117.0(5) . . ?
C63 C62 S3 121.1(5) . . ?
C62 C63 C64 117.9(7) . . ?
C62 C63 H63 121.0 . . ?
C64 C63 H63 121.0 . . ?
C59 C64 C63 122.2(7) . . ?
C59 C64 H64 118.9 . . ?
C63 C64 H64 118.9 . . ?
N8 C65 N7 118.1(6) . . ?
N8 C65 N9 128.0(6) . . ?
N7 C65 N9 113.8(5) . . ?
O7 C66 N9 121.6(6) . . ?
O7 C66 C67 121.5(6) . . ?
N9 C66 C67 116.7(6) . . ?
C68 C67 C73 119.5(6) . . ?
C68 C67 C66 118.1(6) . . ?
C73 C67 C66 122.3(6) . . ?
C67 C68 C69 119.8(7) . . ?
C67 C68 H68 120.1 . . ?
C69 C68 H68 120.1 . . ?
C71 C69 C68 121.1(7) . . ?
C71 C69 H69 119.5 . . ?
C68 C69 H69 119.5 . . ?
C71 C70 H70A 109.5 . . ?
C71 C70 H70B 109.5 . . ?
H70A C70 H70B 109.5 . . ?
C71 C70 H70C 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
C69 C71 C72 118.7(7) . . ?
C69 C71 C70 120.7(7) . . ?
C72 C71 C70 120.6(7) . . ?
C73 C72 C71 121.0(7) . . ?
C73 C72 H72 119.5 . . ?
C71 C72 H72 119.5 . . ?
C72 C73 C67 119.9(6) . . ?
C72 C73 H73 120.0 . . ?
C67 C73 H73 120.0 . . ?
N9 C74 C79 112.5(5) . . ?
N9 C74 C75 111.6(5) . . ?
C79 C74 C75 111.4(5) . . ?
N9 C74 H74 107.0 . . ?
C79 C74 H74 107.0 . . ?
C75 C74 H74 107.0 . . ?
C76 C75 C74 109.6(5) . . ?
C76 C75 H75A 109.7 . . ?
C74 C75 H75A 109.7 . . ?
C76 C75 H75B 109.7 . . ?
C74 C75 H75B 109.7 . . ?
H75A C75 H75B 108.2 . . ?
C77 C76 C75 112.0(5) . . ?
C77 C76 H76A 109.2 . . ?
C75 C76 H76A 109.2 . . ?
C77 C76 H76B 109.2 . . ?
C75 C76 H76B 109.2 . . ?
H76A C76 H76B 107.9 . . ?
C76 C77 C78 109.8(5) . . ?
C76 C77 H77A 109.7 . . ?
C78 C77 H77A 109.7 . . ?
C76 C77 H77B 109.7 . . ?
C78 C77 H77B 109.7 . . ?
H77A C77 H77B 108.2 . . ?
C79 C78 C77 111.7(5) . . ?
C79 C78 H78A 109.3 . . ?
C77 C78 H78A 109.3 . . ?
C79 C78 H78B 109.3 . . ?
C77 C78 H78B 109.3 . . ?
H78A C78 H78B 107.9 . . ?
C78 C79 C74 110.4(5) . . ?
C78 C79 H79A 109.6 . . ?
C74 C79 H79A 109.6 . . ?
C78 C79 H79B 109.6 . . ?
C74 C79 H79B 109.6 . . ?
H79A C79 H79B 108.1 . . ?
N7 C80 C85 110.8(5) . . ?
N7 C80 C81 109.7(5) . . ?
C85 C80 C81 111.4(6) . . ?
N7 C80 H80 108.3 . . ?
C85 C80 H80 108.3 . . ?
C81 C80 H80 108.3 . . ?
C82 C81 C80 109.5(6) . . ?
C82 C81 H81A 109.8 . . ?
C80 C81 H81A 109.8 . . ?
C82 C81 H81B 109.8 . . ?
C80 C81 H81B 109.8 . . ?
H81A C81 H81B 108.2 . . ?
C81 C82 C83 111.3(6) . . ?
C81 C82 H82A 109.4 . . ?
C83 C82 H82A 109.4 . . ?
C81 C82 H82B 109.4 . . ?
C83 C82 H82B 109.4 . . ?
H82A C82 H82B 108.0 . . ?
C82 C83 C84 110.2(6) . . ?
C82 C83 H83A 109.6 . . ?
C84 C83 H83A 109.6 . . ?
C82 C83 H83B 109.6 . . ?
C84 C83 H83B 109.6 . . ?
H83A C83 H83B 108.1 . . ?
C83 C84 C85 110.4(6) . . ?
C83 C84 H84A 109.6 . . ?
C85 C84 H84A 109.6 . . ?
C83 C84 H84B 109.6 . . ?
C85 C84 H84B 109.6 . . ?
H84A C84 H84B 108.1 . . ?
C80 C85 C84 110.9(6) . . ?
C80 C85 H85A 109.5 . . ?
C84 C85 H85A 109.5 . . ?
C80 C85 H85B 109.5 . . ?
C84 C85 H85B 109.5 . . ?
H85A C85 H85B 108.0 . . ?
C87 C86 H86A 109.5 . . ?
C87 C86 H86B 109.5 . . ?
H86A C86 H86B 109.5 . . ?
C87 C86 H86C 109.5 . . ?
H86A C86 H86C 109.5 . . ?
H86B C86 H86C 109.5 . . ?
C88 C87 C92 119.1(7) . . ?
C88 C87 C86 120.1(7) . . ?
C92 C87 C86 120.7(7) . . ?
C87 C88 C89 120.8(7) . . ?
C87 C88 H88 119.6 . . ?
C89 C88 H88 119.6 . . ?
C90 C89 C88 118.9(7) . . ?
C90 C89 H89 120.6 . . ?
C88 C89 H89 120.6 . . ?
C89 C90 C91 121.5(6) . . ?
C89 C90 S4 117.0(5) . . ?
C91 C90 S4 121.3(5) . . ?
C90 C91 C92 118.3(7) . . ?
C90 C91 H91 120.8 . . ?
C92 C91 H91 120.8 . . ?
C91 C92 C87 121.4(7) . . ?
C91 C92 H92 119.3 . . ?
C87 C92 H92 119.3 . . ?
C94 C93 H93A 109.5 . . ?
C94 C93 H93B 109.5 . . ?
H93A C93 H93B 109.5 . . ?
C94 C93 H93C 109.5 . . ?
H93A C93 H93C 109.5 . . ?
H93B C93 H93C 109.5 . . ?
C95 C94 C99 118.1(7) . . ?
C95 C94 C93 120.7(7) . . ?
C99 C94 C93 121.2(8) . . ?
C96 C95 C94 120.8(7) . . ?
C96 C95 H95 119.6 . . ?
C94 C95 H95 119.6 . . ?
C95 C96 C97 121.1(7) . . ?
C95 C96 H96 119.5 . . ?
C97 C96 H96 119.5 . . ?
C96 C97 C98 118.8(7) . . ?
C96 C97 C100 123.9(6) . . ?
C98 C97 C100 117.2(6) . . ?
C99 C98 C97 120.3(7) . . ?
C99 C98 H98 119.9 . . ?
C97 C98 H98 119.9 . . ?
C98 C99 C94 120.9(7) . . ?
C98 C99 H99 119.6 . . ?
C94 C99 H99 119.6 . . ?
O10 C100 N10 121.9(6) . . ?
O10 C100 C97 120.8(6) . . ?
N10 C100 C97 117.2(6) . . ?
N12 C101 N11 120.1(6) . . ?
N12 C101 N10 126.1(6) . . ?
N11 C101 N10 113.8(5) . . ?
C103 C102 C107 110.0(5) . . ?
C103 C102 H10I 109.7 . . ?
C107 C102 H10I 109.7 . . ?
C103 C102 H10J 109.7 . . ?
C107 C102 H10J 109.7 . . ?
H10I C102 H10J 108.2 . . ?
N10 C103 C104 112.8(5) . . ?
N10 C103 C102 112.5(5) . . ?
C104 C103 C102 110.6(6) . . ?
N10 C103 H103 106.8 . . ?
C104 C103 H103 106.8 . . ?
C102 C103 H103 106.8 . . ?
C103 C104 C105 110.7(5) . . ?
C103 C104 H10G 109.5 . . ?
C105 C104 H10G 109.5 . . ?
C103 C104 H10H 109.5 . . ?
C105 C104 H10H 109.5 . . ?
H10G C104 H10H 108.1 . . ?
C106 C105 C104 111.8(5) . . ?
C106 C105 H10E 109.3 . . ?
C104 C105 H10E 109.3 . . ?
C106 C105 H10F 109.3 . . ?
C104 C105 H10F 109.3 . . ?
H10E C105 H10F 107.9 . . ?
C107 C106 C105 111.6(6) . . ?
C107 C106 H10C 109.3 . . ?
C105 C106 H10C 109.3 . . ?
C107 C106 H10D 109.3 . . ?
C105 C106 H10D 109.3 . . ?
H10C C106 H10D 108.0 . . ?
C106 C107 C102 112.3(6) . . ?
C106 C107 H10K 109.2 . . ?
C102 C107 H10K 109.2 . . ?
C106 C107 H10L 109.2 . . ?
C102 C107 H10L 109.2 . . ?
H10K C107 H10L 107.9 . . ?
C109 C108 C110 111.1(5) . . ?
C109 C108 H10A 109.4 . . ?
C110 C108 H10A 109.4 . . ?
C109 C108 H10B 109.4 . . ?
C110 C108 H10B 109.4 . . ?
H10A C108 H10B 108.0 . . ?
N11 C109 C108 108.7(5) . . ?
N11 C109 C112 110.7(5) . . ?
C108 C109 C112 111.3(6) . . ?
N11 C109 H109 108.7 . . ?
C108 C109 H109 108.7 . . ?
C112 C109 H109 108.7 . . ?
C111 C110 C108 110.6(6) . . ?
C111 C110 H11G 109.5 . . ?
C108 C110 H11G 109.5 . . ?
C111 C110 H11H 109.5 . . ?
C108 C110 H11H 109.5 . . ?
H11G C110 H11H 108.1 . . ?
C113 C111 C110 111.4(6) . . ?
C113 C111 H11A 109.3 . . ?
C110 C111 H11A 109.3 . . ?
C113 C111 H11B 109.3 . . ?
C110 C111 H11B 109.3 . . ?
H11A C111 H11B 108.0 . . ?
C109 C112 C113 110.9(6) . . ?
C109 C112 H11C 109.5 . . ?
C113 C112 H11C 109.5 . . ?
C109 C112 H11D 109.5 . . ?
C113 C112 H11D 109.5 . . ?
H11C C112 H11D 108.1 . . ?
C111 C113 C112 112.2(6) . . ?
C111 C113 H11E 109.2 . . ?
C112 C113 H11E 109.2 . . ?
C111 C113 H11F 109.2 . . ?
C112 C113 H11F 109.2 . . ?
H11E C113 H11F 107.9 . . ?
C14 N1 S1 125.5(5) . . ?
C14 N2 C15 124.9(5) . . ?
C14 N2 H2 117.5 . . ?
C15 N2 H2 117.5 . . ?
C22 N3 C14 121.8(6) . . ?
C22 N3 C13 117.9(5) . . ?
C14 N3 C13 118.8(5) . . ?
C57 N4 S2 127.1(5) . . ?
C57 N5 C44 122.5(5) . . ?
C57 N5 H5 118.7 . . ?
C44 N5 H5 118.7 . . ?
C36 N6 C57 122.4(5) . . ?
C36 N6 C30 118.9(5) . . ?
C57 N6 C30 117.5(5) . . ?
C65 N7 C80 122.8(5) . . ?
C65 N7 H7 118.6 . . ?
C80 N7 H7 118.6 . . ?
C65 N8 S3 125.3(5) . . ?
C66 N9 C65 121.3(5) . . ?
C66 N9 C74 118.1(5) . . ?
C65 N9 C74 118.4(5) . . ?
C100 N10 C101 122.3(5) . . ?
C100 N10 C103 117.9(5) . . ?
C101 N10 C103 118.3(5) . . ?
C101 N11 C109 125.5(5) . . ?
C101 N11 H11 117.2 . . ?
C109 N11 H11 117.2 . . ?
C101 N12 S4 125.3(5) . . ?
O3 S1 O2 115.0(3) . . ?
O3 S1 N1 116.5(3) . . ?
O2 S1 N1 107.1(3) . . ?
O3 S1 C5 108.8(3) . . ?
O2 S1 C5 106.4(3) . . ?
N1 S1 C5 101.9(3) . . ?
O5 S2 O4 115.8(3) . . ?
O5 S2 N4 116.4(3) . . ?
O4 S2 N4 106.0(3) . . ?
O5 S2 C50 108.6(3) . . ?
O4 S2 C50 107.4(3) . . ?
N4 S2 C50 101.4(3) . . ?
O9 S3 O8 115.6(3) . . ?
O9 S3 N8 116.0(3) . . ?
O8 S3 N8 106.4(3) . . ?
O9 S3 C62 108.5(3) . . ?
O8 S3 C62 107.0(3) . . ?
N8 S3 C62 102.2(3) . . ?
O12 S4 O11 115.1(3) . . ?
O12 S4 N12 116.6(3) . . ?
O11 S4 N12 107.2(3) . . ?
O12 S4 C90 108.5(3) . . ?
O11 S4 C90 106.3(3) . . ?
N12 S4 C90 101.9(3) . . ?

_refine_diff_density_max         0.567
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1494037'
_audit_update_record             
;
2016-07-16 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H20 N2 O5 S'
_chemical_formula_weight         340.39

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.7492(7)
_cell_length_b                   7.2139(7)
_cell_length_c                   31.441(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1530.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9972
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      37.57

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    0.240
_shelx_estimated_absorpt_T_min   0.730
_shelx_estimated_absorpt_T_max   0.831
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60042
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         2.591
_diffrn_reflns_theta_max         37.839
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8232
_reflns_number_gt                7166
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+0.3197P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8232
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1030
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
C1 C 0.6915(2) 0.74216(19) 0.45499(4) 0.0129(2) Uani 1 1 d . . . . .
H1 H 0.6915 0.6164 0.4484 0.015 Uiso 1 1 calc R U . . .
C2 C 0.6931(3) 0.8763(2) 0.42300(4) 0.0144(2) Uani 1 1 d . . . . .
H2A H 0.6950 0.8394 0.3947 0.017 Uiso 1 1 calc R U . . .
C3 C 0.6917(3) 1.0649(2) 0.43287(4) 0.0152(2) Uani 1 1 d . . . . .
H3 H 0.6925 1.1514 0.4109 0.018 Uiso 1 1 calc R U . . .
C4 C 0.6892(3) 1.12660(19) 0.47492(4) 0.0142(2) Uani 1 1 d . . . . .
H4 H 0.6875 1.2521 0.4817 0.017 Uiso 1 1 calc R U . . .
C5 C 0.6902(2) 0.80269(18) 0.49700(4) 0.0107(2) Uani 1 1 d . . . . .
C6 C 0.6892(2) 0.99094(18) 0.50606(4) 0.0112(2) Uani 1 1 d . . . . .
C7 C 0.6901(2) 0.68350(18) 0.53533(4) 0.0110(2) Uani 1 1 d . . . . .
C8 C 0.6854(3) 0.74506(18) 0.61556(4) 0.0127(2) Uani 1 1 d . . . . .
C9 C 0.6925(3) 0.49453(19) 0.66760(4) 0.0148(2) Uani 1 1 d . . . . .
H9 H 0.6636 0.5980 0.6868 0.018 Uiso 1 1 calc R U . . .
C10 C 0.5327(3) 0.3474(2) 0.67353(5) 0.0171(3) Uani 1 1 d . . . . .
H10A H 0.5522 0.2487 0.6530 0.021 Uiso 1 1 calc R U . . .
H10B H 0.4034 0.4019 0.6685 0.021 Uiso 1 1 calc R U . . .
C11 C 0.5401(3) 0.2669(2) 0.71876(5) 0.0179(3) Uani 1 1 d . . . . .
H11A H 0.5063 0.3631 0.7391 0.022 Uiso 1 1 calc R U . . .
H11B H 0.4427 0.1687 0.7213 0.022 Uiso 1 1 calc R U . . .
C12 C 0.7447(3) 0.1902(2) 0.72917(5) 0.0175(3) Uani 1 1 d . . . . .
H12A H 0.7738 0.0863 0.7106 0.021 Uiso 1 1 calc R U . . .
H12B H 0.7466 0.1460 0.7583 0.021 Uiso 1 1 calc R U . . .
C13 C 0.9022(3) 0.3400(3) 0.72344(5) 0.0200(3) Uani 1 1 d . . . . .
H13A H 1.0320 0.2877 0.7291 0.024 Uiso 1 1 calc R U . . .
H13B H 0.8794 0.4389 0.7438 0.024 Uiso 1 1 calc R U . . .
C14 C 0.8981(3) 0.4197(3) 0.67829(5) 0.0194(3) Uani 1 1 d . . . . .
H14A H 0.9947 0.5188 0.6760 0.023 Uiso 1 1 calc R U . . .
H14B H 0.9338 0.3237 0.6581 0.023 Uiso 1 1 calc R U . . .
C15 C 0.1639(3) 0.9747(3) 0.65825(7) 0.0304(4) Uani 1 1 d . . . . .
H15A H 0.1837 1.0770 0.6773 0.046 Uiso 1 1 calc R U . . .
H15B H 0.0280 0.9358 0.6594 0.046 Uiso 1 1 calc R U . . .
H15C H 0.1960 1.0121 0.6298 0.046 Uiso 1 1 calc R U . . .
N1 N 0.6892(2) 0.79692(16) 0.57155(4) 0.01146(18) Uani 1 1 d . . . . .
N2 N 0.6888(2) 0.56461(16) 0.62364(4) 0.0154(2) Uani 1 1 d . . . . .
H2 H 0.6889 0.4872 0.6028 0.018 Uiso 1 1 calc R U . . .
O1 O 0.49860(19) 1.10672(17) 0.57384(4) 0.0176(2) Uani 1 1 d . . . . .
O2 O 0.86373(19) 1.11453(18) 0.57544(4) 0.0185(2) Uani 1 1 d . . . . .
O3 O 0.6768(2) 0.87116(16) 0.64151(4) 0.0193(2) Uani 1 1 d . . . . .
O4 O 0.2875(3) 0.8262(2) 0.67040(5) 0.0333(3) Uani 1 1 d . . . . .
H4A H 0.4036 0.8547 0.6664 0.050 Uiso 1 1 calc R U . . .
O5 O 0.6919(2) 0.51553(14) 0.53620(3) 0.01562(18) Uani 1 1 d . . . . .
S1 S 0.68456(6) 1.03021(4) 0.56100(2) 0.01108(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C5 1.3913(19) . ?
C1 C2 1.396(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.396(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.395(2) . ?
C3 H3 0.9300 . ?
C4 C6 1.3843(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.3876(18) . ?
C5 C7 1.4805(18) . ?
C6 S1 1.7506(13) . ?
C7 O5 1.2121(16) . ?
C7 N1 1.4023(17) . ?
C8 O3 1.2233(17) . ?
C8 N2 1.3266(18) . ?
C8 N1 1.4336(17) . ?
C9 N2 1.4720(18) . ?
C9 C10 1.525(2) . ?
C9 C14 1.527(2) . ?
C9 H9 0.9800 . ?
C10 C11 1.537(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.523(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.527(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.532(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O4 1.410(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N1 S1 1.7156(12) . ?
N2 H2 0.8600 . ?
O1 S1 1.4293(13) . ?
O2 S1 1.4278(12) . ?
O4 H4A 0.8200 . ?

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
C5 C1 C2 117.81(12) . . ?
C5 C1 H1 121.1 . . ?
C2 C1 H1 121.1 . . ?
C3 C2 C1 121.05(13) . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 H2A 119.5 . . ?
C4 C3 C2 121.44(13) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C6 C4 C3 116.42(13) . . ?
C6 C4 H4 121.8 . . ?
C3 C4 H4 121.8 . . ?
C6 C5 C1 120.14(12) . . ?
C6 C5 C7 113.66(11) . . ?
C1 C5 C7 126.20(12) . . ?
C4 C6 C5 123.14(12) . . ?
C4 C6 S1 125.69(10) . . ?
C5 C6 S1 111.16(9) . . ?
O5 C7 N1 124.41(12) . . ?
O5 C7 C5 126.79(12) . . ?
N1 C7 C5 108.80(10) . . ?
O3 C8 N2 127.07(13) . . ?
O3 C8 N1 116.78(12) . . ?
N2 C8 N1 116.15(12) . . ?
N2 C9 C10 110.00(13) . . ?
N2 C9 C14 110.08(13) . . ?
C10 C9 C14 111.72(13) . . ?
N2 C9 H9 108.3 . . ?
C10 C9 H9 108.3 . . ?
C14 C9 H9 108.3 . . ?
C9 C10 C11 110.68(13) . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C10 111.44(14) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 110.44(14) . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 111.24(14) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C9 C14 C13 110.68(14) . . ?
C9 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C8 129.17(11) . . ?
C7 N1 S1 114.54(9) . . ?
C8 N1 S1 116.26(9) . . ?
C8 N2 C9 121.15(12) . . ?
C8 N2 H2 119.4 . . ?
C9 N2 H2 119.4 . . ?
C15 O4 H4A 109.5 . . ?
O2 S1 O1 119.30(7) . . ?
O2 S1 N1 109.93(7) . . ?
O1 S1 N1 109.90(8) . . ?
O2 S1 C6 111.56(8) . . ?
O1 S1 C6 110.91(7) . . ?
N1 S1 C6 91.82(6) . . ?

_refine_diff_density_max         0.503
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1494038'
_audit_update_record             
;
2016-07-16 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 Cl N2 O4 S'
_chemical_formula_weight         288.70

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'
Cl Cl 0.1484 0.1585 '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                   11.8316(16)
_cell_length_b                   14.0713(19)
_cell_length_c                   7.0351(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.718(2)
_cell_angle_gamma                90
_cell_volume                     1163.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3505
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      25.18

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.516
_shelx_estimated_absorpt_T_min   0.745
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11594
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.733
_diffrn_reflns_theta_max         25.426
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2137
_reflns_number_gt                1808
_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-2013 (Sheldrick, 2013)'
_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)+(0.0375P)²+0.6644P] 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         2137
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
C1 C 0.32533(19) 0.36404(16) 0.7737(3) 0.0293(5) Uani 1 1 d . . . . .
H1 H 0.2669 0.3600 0.8552 0.035 Uiso 1 1 calc R U . . .
C2 C 0.43752(19) 0.37120(15) 0.8537(3) 0.0267(5) Uani 1 1 d . . . . .
H4 H 0.4574 0.3722 0.9885 0.032 Uiso 1 1 calc R U . . .
C3 C 0.51931(17) 0.37679(13) 0.7293(3) 0.0193(4) Uani 1 1 d . . . . .
C4 C 0.80703(18) 0.40213(14) 0.5146(3) 0.0249(5) Uani 1 1 d . . . . .
C5 C 0.9295(2) 0.42216(18) 0.2609(4) 0.0394(6) Uani 1 1 d . . . . .
H7 H 0.9870 0.4422 0.3670 0.047 Uiso 1 1 calc R U . . .
H8 H 0.9272 0.4705 0.1583 0.047 Uiso 1 1 calc R U . . .
C6 C 0.96194(19) 0.32888(17) 0.1862(4) 0.0367(6) Uani 1 1 d . . . . .
H2 H 0.9062 0.3101 0.0767 0.044 Uiso 1 1 calc R U . . .
H9 H 0.9612 0.2800 0.2872 0.044 Uiso 1 1 calc R U . . .
C7 C 0.49188(17) 0.37623(13) 0.5324(3) 0.0183(4) Uani 1 1 d . . . . .
C8 C 0.37977(17) 0.36909(14) 0.4529(3) 0.0223(4) Uani 1 1 d . . . . .
H6 H 0.3604 0.3686 0.3180 0.027 Uiso 1 1 calc R U . . .
C9 C 0.29628(18) 0.36265(15) 0.5751(3) 0.0259(5) Uani 1 1 d . . . . .
H5 H 0.2187 0.3572 0.5236 0.031 Uiso 1 1 calc R U . . .
C10 C 0.59195(17) 0.38735(13) 0.4267(3) 0.0206(4) Uani 1 1 d . . . . .
N1 N 0.69044(14) 0.39355(12) 0.5560(2) 0.0202(4) Uani 1 1 d . . . . .
N2 N 0.81803(15) 0.41554(14) 0.3297(3) 0.0310(5) Uani 1 1 d . . . . .
H3 H 0.7564 0.4205 0.2471 0.037 Uiso 1 1 calc R U . . .
O1 O 0.88144(13) 0.39886(11) 0.6475(2) 0.0344(4) Uani 1 1 d . . . . .
O2 O 0.69786(12) 0.47334(10) 0.8862(2) 0.0271(4) Uani 1 1 d . . . . .
O3 O 0.71312(13) 0.29956(11) 0.8738(2) 0.0305(4) Uani 1 1 d . . . . .
O4 O 0.58955(13) 0.39216(11) 0.2538(2) 0.0298(4) Uani 1 1 d . . . . .
S1 S 0.66734(4) 0.38588(4) 0.79129(7) 0.02048(16) Uani 1 1 d . . . . .
Cl1 Cl 1.10155(5) 0.33600(5) 0.11084(9) 0.0435(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(3) . ?
C1 C9 1.399(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.381(3) . ?
C2 H4 0.9500 . ?
C3 C7 1.385(3) . ?
C3 S1 1.759(2) . ?
C4 O1 1.208(3) . ?
C4 N2 1.335(3) . ?
C4 N1 1.448(3) . ?
C5 N2 1.460(3) . ?
C5 C6 1.481(3) . ?
C5 H7 0.9900 . ?
C5 H8 0.9900 . ?
C6 Cl1 1.796(2) . ?
C6 H2 0.9900 . ?
C6 H9 0.9900 . ?
C7 C8 1.381(3) . ?
C7 C10 1.478(3) . ?
C8 C9 1.387(3) . ?
C8 H6 0.9500 . ?
C9 H5 0.9500 . ?
C10 O4 1.215(2) . ?
C10 N1 1.395(3) . ?
N1 S1 1.7124(17) . ?
N2 H3 0.8800 . ?
O2 S1 1.4262(15) . ?
O3 S1 1.4256(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 121.3(2) . . ?
C2 C1 H1 119.4 . . ?
C9 C1 H1 119.4 . . ?
C3 C2 C1 117.16(19) . . ?
C3 C2 H4 121.4 . . ?
C1 C2 H4 121.4 . . ?
C2 C3 C7 122.27(19) . . ?
C2 C3 S1 126.73(16) . . ?
C7 C3 S1 111.00(15) . . ?
O1 C4 N2 127.9(2) . . ?
O1 C4 N1 117.80(19) . . ?
N2 C4 N1 114.29(18) . . ?
N2 C5 C6 110.04(19) . . ?
N2 C5 H7 109.7 . . ?
C6 C5 H7 109.7 . . ?
N2 C5 H8 109.7 . . ?
C6 C5 H8 109.7 . . ?
H7 C5 H8 108.2 . . ?
C5 C6 Cl1 109.94(17) . . ?
C5 C6 H2 109.7 . . ?
Cl1 C6 H2 109.7 . . ?
C5 C6 H9 109.7 . . ?
Cl1 C6 H9 109.7 . . ?
H2 C6 H9 108.2 . . ?
C8 C7 C3 120.44(18) . . ?
C8 C7 C10 126.28(18) . . ?
C3 C7 C10 113.24(18) . . ?
C7 C8 C9 118.27(19) . . ?
C7 C8 H6 120.9 . . ?
C9 C8 H6 120.9 . . ?
C8 C9 C1 120.6(2) . . ?
C8 C9 H5 119.7 . . ?
C1 C9 H5 119.7 . . ?
O4 C10 N1 124.70(19) . . ?
O4 C10 C7 125.66(19) . . ?
N1 C10 C7 109.63(16) . . ?
C10 N1 C4 128.09(17) . . ?
C10 N1 S1 114.26(13) . . ?
C4 N1 S1 117.61(14) . . ?
C4 N2 C5 121.8(2) . . ?
C4 N2 H3 119.1 . . ?
C5 N2 H3 119.1 . . ?
O3 S1 O2 118.77(9) . . ?
O3 S1 N1 110.56(9) . . ?
O2 S1 N1 109.74(9) . . ?
O3 S1 C3 111.03(9) . . ?
O2 S1 C3 111.65(9) . . ?
N1 S1 C3 91.82(9) . . ?

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
C9 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C7 0.6(3) . . . . ?
C1 C2 C3 S1 -179.74(16) . . . . ?
N2 C5 C6 Cl1 -177.64(17) . . . . ?
C2 C3 C7 C8 -0.6(3) . . . . ?
S1 C3 C7 C8 179.69(15) . . . . ?
C2 C3 C7 C10 177.31(18) . . . . ?
S1 C3 C7 C10 -2.4(2) . . . . ?
C3 C7 C8 C9 0.1(3) . . . . ?
C10 C7 C8 C9 -177.54(18) . . . . ?
C7 C8 C9 C1 0.4(3) . . . . ?
C2 C1 C9 C8 -0.4(3) . . . . ?
C8 C7 C10 O4 0.3(3) . . . . ?
C3 C7 C10 O4 -177.44(19) . . . . ?
C8 C7 C10 N1 179.07(18) . . . . ?
C3 C7 C10 N1 1.3(2) . . . . ?
O4 C10 N1 C4 -3.1(3) . . . . ?
C7 C10 N1 C4 178.09(17) . . . . ?
O4 C10 N1 S1 179.20(16) . . . . ?
C7 C10 N1 S1 0.4(2) . . . . ?
O1 C4 N1 C10 -174.18(19) . . . . ?
N2 C4 N1 C10 7.6(3) . . . . ?
O1 C4 N1 S1 3.4(2) . . . . ?
N2 C4 N1 S1 -174.82(14) . . . . ?
O1 C4 N2 C5 4.3(3) . . . . ?
N1 C4 N2 C5 -177.68(18) . . . . ?
C6 C5 N2 C4 97.1(3) . . . . ?
C10 N1 S1 O3 111.77(14) . . . . ?
C4 N1 S1 O3 -66.16(16) . . . . ?
C10 N1 S1 O2 -115.32(14) . . . . ?
C4 N1 S1 O2 66.75(16) . . . . ?
C10 N1 S1 C3 -1.51(15) . . . . ?
C4 N1 S1 C3 -179.45(14) . . . . ?
C2 C3 S1 O3 69.6(2) . . . . ?
C7 C3 S1 O3 -110.64(15) . . . . ?
C2 C3 S1 O2 -65.4(2) . . . . ?
C7 C3 S1 O2 114.34(15) . . . . ?
C2 C3 S1 N1 -177.48(19) . . . . ?
C7 C3 S1 N1 2.24(15) . . . . ?

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
N2 H3 O2 0.88 2.66 3.374(2) 139.1 1_554
N2 H3 O4 0.88 2.02 2.714(2) 134.8 .
C2 H4 O4 0.95 2.31 3.172(3) 151.0 1_556
C6 H2 O3 0.99 2.55 3.486(3) 157.2 1_554
N2 H3 O2 0.88 2.66 3.374(2) 139.1 1_554
N2 H3 O4 0.88 2.02 2.714(2) 134.8 .
C2 H4 O4 0.95 2.31 3.172(3) 151.0 1_556
C6 H2 O3 0.99 2.55 3.486(3) 157.2 1_554

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1494039'
_audit_update_record             
;
2016-07-16 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 N2 O4 S'
_chemical_formula_weight         302.30

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                   6.4988(6)
_cell_length_b                   15.6631(14)
_cell_length_c                   12.8234(14)
_cell_angle_alpha                90
_cell_angle_beta                 100.670(4)
_cell_angle_gamma                90
_cell_volume                     1282.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5577
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      25.04

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    0.271
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18893
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.062
_diffrn_reflns_theta_max         25.042
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             2262
_reflns_number_gt                1842
_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-2013 (Sheldrick, 2013)'
_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)+(0.0397P)²+0.5277P] 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         2262
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0790
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
C1 C -0.1510(3) 0.81061(12) 0.59882(16) 0.0126(4) Uani 1 1 d . . . . .
H1 H -0.2053 0.8144 0.5266 0.015 Uiso 1 1 calc R U . . .
C2 C -0.2546(3) 0.84607(12) 0.67432(16) 0.0143(4) Uani 1 1 d . . . . .
H2A H -0.3814 0.8740 0.6521 0.017 Uiso 1 1 calc R U . . .
C3 C -0.1721(3) 0.84057(12) 0.78282(16) 0.0147(5) Uani 1 1 d . . . . .
H3 H -0.2439 0.8654 0.8314 0.018 Uiso 1 1 calc R U . . .
C4 C 0.0162(3) 0.79839(12) 0.81920(16) 0.0131(4) Uani 1 1 d . . . . .
H4 H 0.0712 0.7945 0.8914 0.016 Uiso 1 1 calc R U . . .
C5 C 0.1192(3) 0.76228(12) 0.74432(15) 0.0102(4) Uani 1 1 d . . . . .
C6 C 0.0368(3) 0.76942(12) 0.63652(15) 0.0107(4) Uani 1 1 d . . . . .
C7 C 0.5541(3) 0.63881(12) 0.65658(16) 0.0128(4) Uani 1 1 d . . . . .
C8 C 0.8712(3) 0.56937(12) 0.75955(16) 0.0128(4) Uani 1 1 d . . . . .
C008 C 0.3170(3) 0.71338(12) 0.76788(15) 0.0103(4) Uani 1 1 d . . . . .
C9 C 0.9430(3) 0.53152(13) 0.67464(16) 0.0158(5) Uani 1 1 d . . . . .
H9 H 0.8655 0.5354 0.6061 0.019 Uiso 1 1 calc R U . . .
C10 C 1.1335(3) 0.48770(13) 0.69442(17) 0.0180(5) Uani 1 1 d . . . . .
H10 H 1.1829 0.4624 0.6383 0.022 Uiso 1 1 calc R U . . .
C11 C 1.2507(3) 0.48126(13) 0.79667(17) 0.0188(5) Uani 1 1 d . . . . .
H11 H 1.3777 0.4522 0.8087 0.023 Uiso 1 1 calc R U . . .
C12 C 1.1759(3) 0.51856(13) 0.88016(17) 0.0180(5) Uani 1 1 d . . . . .
H12 H 1.2523 0.5138 0.9488 0.022 Uiso 1 1 calc R U . . .
C13 C 0.9875(3) 0.56303(13) 0.86209(17) 0.0164(5) Uani 1 1 d . . . . .
H13 H 0.9390 0.5885 0.9184 0.020 Uiso 1 1 calc R U . . .
N1 N 0.3736(2) 0.68729(10) 0.67249(12) 0.0112(4) Uani 1 1 d . . . . .
N2 N 0.6802(2) 0.61619(10) 0.74809(13) 0.0134(4) Uani 1 1 d . . . . .
H2 H 0.6413 0.6317 0.8058 0.016 Uiso 1 1 calc R U . . .
O1 O 0.3116(2) 0.78472(9) 0.51010(10) 0.0142(3) Uani 1 1 d . . . . .
O2 O 0.1098(2) 0.65053(9) 0.50121(10) 0.0153(3) Uani 1 1 d . . . . .
O3 O 0.4165(2) 0.69703(9) 0.85526(10) 0.0146(3) Uani 1 1 d . . . . .
O4 O 0.5749(2) 0.62400(9) 0.56627(11) 0.0186(3) Uani 1 1 d . . . . .
S1 S 0.20511(7) 0.72167(3) 0.56045(4) 0.01060(15) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.386(3) . ?
C1 C2 1.393(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.398(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(3) . ?
C5 C008 1.479(3) . ?
C6 S1 1.7615(19) . ?
C7 O4 1.213(2) . ?
C7 N2 1.349(3) . ?
C7 N1 1.443(2) . ?
C8 C13 1.394(3) . ?
C8 C9 1.394(3) . ?
C8 N2 1.425(2) . ?
C008 O3 1.213(2) . ?
C008 N1 1.402(2) . ?
C9 C10 1.397(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.393(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N1 S1 1.7236(16) . ?
N2 H2 0.8600 . ?
O1 S1 1.4271(14) . ?
O2 S1 1.4241(14) . ?

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
C6 C1 C2 116.79(18) . . ?
C6 C1 H1 121.6 . . ?
C2 C1 H1 121.6 . . ?
C1 C2 C3 121.44(19) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
C4 C3 C2 120.92(18) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 117.88(18) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C4 C5 C6 120.53(18) . . ?
C4 C5 C008 125.58(18) . . ?
C6 C5 C008 113.89(17) . . ?
C1 C6 C5 122.43(18) . . ?
C1 C6 S1 126.98(15) . . ?
C5 C6 S1 110.59(14) . . ?
O4 C7 N2 128.57(18) . . ?
O4 C7 N1 118.21(18) . . ?
N2 C7 N1 113.22(16) . . ?
C13 C8 C9 120.35(19) . . ?
C13 C8 N2 116.33(18) . . ?
C9 C8 N2 123.31(18) . . ?
O3 C008 N1 124.28(18) . . ?
O3 C008 C5 126.36(17) . . ?
N1 C008 C5 109.36(16) . . ?
C8 C9 C10 118.73(19) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 121.22(19) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C12 C11 C10 119.24(19) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 119.99(19) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C008 N1 C7 128.93(16) . . ?
C008 N1 S1 114.03(13) . . ?
C7 N1 S1 117.01(13) . . ?
C7 N2 C8 127.04(16) . . ?
C7 N2 H2 116.5 . . ?
C8 N2 H2 116.5 . . ?
O2 S1 O1 119.97(8) . . ?
O2 S1 N1 110.29(8) . . ?
O1 S1 N1 107.87(8) . . ?
O2 S1 C6 111.97(9) . . ?
O1 S1 C6 111.08(9) . . ?
N1 S1 C6 92.00(9) . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-4

