# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 
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data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1402381'
_audit_update_record             
;
2015-05-22 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 N2 O4 S'
_chemical_formula_sum            'C21 H20 N2 O4 S'
_chemical_formula_weight         396.45

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.979(4)
_cell_length_b                   10.358(5)
_cell_length_c                   12.109(6)
_cell_angle_alpha                68.918(5)
_cell_angle_beta                 67.153(4)
_cell_angle_gamma                88.425(6)
_cell_volume                     960.1(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      22.85
_cell_measurement_theta_max      42.53

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    1.757
_shelx_estimated_absorpt_T_min   0.547
_shelx_estimated_absorpt_T_max   0.830
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.6965
_exptl_absorpt_correction_T_max  0.8183
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   7
Theta correction was applied.
Weighted transmission curves were used.
No Fourier smoothing was applied.
;


_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 1 -5
-2 4 3
-4 -2 -1
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4133
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.281
_diffrn_reflns_theta_max         74.082
_diffrn_reflns_theta_full        67.684
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3877
_reflns_number_gt                3207
_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       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_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)+(0.0849P)²+0.1293P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0053(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3877
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1280
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.75005(5) -0.42130(4) 0.51948(4) 0.05747(17) Uani 1 1 d . . . . .
O1 O 0.79715(19) -0.55407(13) 0.57676(14) 0.0719(4) Uani 1 1 d . . . . .
O2 O 0.59594(18) -0.38494(16) 0.58693(15) 0.0785(4) Uani 1 1 d . . . . .
C1 C 0.7623(2) -0.40358(19) 0.36593(19) 0.0576(4) Uani 1 1 d . . . . .
C2 C 0.8855(3) -0.4541(2) 0.2883(2) 0.0739(6) Uani 1 1 d . . . . .
H2 H 0.9556 -0.5069 0.3204 0.089 Uiso 1 1 calc R U . . .
C3 C 0.9046(3) -0.4264(3) 0.1630(2) 0.0827(7) Uani 1 1 d . . . . .
H3 H 0.9885 -0.4609 0.1115 0.099 Uiso 1 1 calc R U . . .
C4 C 0.8031(3) -0.3493(2) 0.1123(2) 0.0687(5) Uani 1 1 d . . . . .
C5 C 0.6799(3) -0.3018(3) 0.1910(3) 0.0895(7) Uani 1 1 d . . . . .
H5 H 0.6088 -0.2504 0.1590 0.107 Uiso 1 1 calc R U . . .
C6 C 0.6578(3) -0.3280(3) 0.3169(2) 0.0842(7) Uani 1 1 d . . . . .
H6 H 0.5725 -0.2947 0.3685 0.101 Uiso 1 1 calc R U . . .
N1 N 0.8881(2) -0.30495(15) 0.49507(15) 0.0563(4) Uani 1 1 d . . . . .
C7 C 0.8778(3) -0.15818(17) 0.42402(17) 0.0587(4) Uani 1 1 d . . . . .
H7A H 0.8168 -0.1559 0.3726 0.070 Uiso 1 1 calc R U . . .
H7B H 0.9871 -0.1116 0.3647 0.070 Uiso 1 1 calc R U . . .
C8 C 0.7987(2) -0.07758(16) 0.50859(15) 0.0472(4) Uani 1 1 d . . . . .
C9 C 0.7817(3) -0.12131(19) 0.63626(17) 0.0598(4) Uani 1 1 d . . . . .
H9 H 0.8146 -0.2061 0.6733 0.072 Uiso 1 1 calc R U . . .
C10 C 0.7168(3) -0.0412(2) 0.70893(19) 0.0724(6) Uani 1 1 d . . . . .
H10 H 0.7041 -0.0731 0.7947 0.087 Uiso 1 1 calc R U . . .
C11 C 0.6710(4) 0.0851(3) 0.6547(2) 0.0841(7) Uani 1 1 d . . . . .
H11 H 0.6299 0.1401 0.7032 0.101 Uiso 1 1 calc R U . . .
C12 C 0.6857(3) 0.1312(2) 0.5286(2) 0.0766(6) Uani 1 1 d . . . . .
H12 H 0.6551 0.2174 0.4920 0.092 Uiso 1 1 calc R U . . .
C13 C 0.7460(2) 0.04917(17) 0.45610(15) 0.0504(4) Uani 1 1 d . . . . .
C14 C 0.6816(2) 0.18446(17) 0.27794(16) 0.0526(4) Uani 1 1 d . . . . .
H14 H 0.6170 0.2325 0.3269 0.063 Uiso 1 1 calc R U . A 2
C15 C 0.6929(2) 0.21705(17) 0.14918(15) 0.0485(4) Uani 1 1 d . . . . .
C20 C 0.7827(2) 0.14097(17) 0.07574(16) 0.0492(4) Uani 1 1 d . . . . .
C19 C 0.7841(2) 0.1699(2) -0.04756(17) 0.0583(4) Uani 1 1 d . . . . .
C18 C 0.7014(3) 0.2732(2) -0.09573(18) 0.0632(5) Uani 1 1 d . . . . .
H18 H 0.7038 0.2926 -0.1776 0.076 Uiso 1 1 calc R U . . .
C17 C 0.6140(3) 0.3493(2) -0.02347(19) 0.0674(5) Uani 1 1 d . . . . .
H17 H 0.5588 0.4192 -0.0575 0.081 Uiso 1 1 calc R U . . .
C16 C 0.6087(3) 0.3220(2) 0.09741(19) 0.0654(5) Uani 1 1 d . . . . .
H16 H 0.5493 0.3730 0.1454 0.078 Uiso 1 1 calc R U . . .
C40 C 0.8300(4) -0.3136(3) -0.0270(3) 0.0919(7) Uani 1 1 d . . . . .
H40A H 0.9214 -0.3555 -0.0674 0.138 Uiso 0.50(4) 1 calc R U P B 1
H40B H 0.8515 -0.2141 -0.0722 0.138 Uiso 0.50(4) 1 calc R U P B 1
H40C H 0.7343 -0.3485 -0.0300 0.138 Uiso 0.50(4) 1 calc R U P B 1
H40D H 0.7501 -0.2566 -0.0457 0.138 Uiso 0.50(4) 1 calc R U P B 2
H40E H 0.8200 -0.3980 -0.0409 0.138 Uiso 0.50(4) 1 calc R U P B 2
H40F H 0.9371 -0.2636 -0.0830 0.138 Uiso 0.50(4) 1 calc R U P B 2
N2 N 0.75875(19) 0.09048(15) 0.32722(14) 0.0519(3) Uani 1 1 d . . . C 2
O3 O 0.86699(19) 0.04207(14) 0.11858(13) 0.0674(4) Uani 1 1 d . . . D 2
O4 O 0.8687(3) 0.0975(2) -0.11988(16) 0.0929(6) Uani 1 1 d . . . E 2
H1A H 0.980(3) -0.333(3) 0.474(2) 0.086(8) Uiso 1 1 d . . . F 2
H3P H 0.846(6) 0.044(4) 0.199(6) 0.103(19) Uiso 0.67(7) 1 d . . P G 3
H3P' H 0.803(6) 0.048(5) 0.288(6) 0.03(2) Uiso 0.33(7) 1 d . . P G 4
H4P H 0.937(5) 0.055(4) -0.092(4) 0.139(13) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4278(15) . ?
S1 O1 1.4355(13) . ?
S1 N1 1.6177(19) . ?
S1 C1 1.761(2) . ?
C1 C2 1.377(3) . ?
C1 C6 1.380(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(3) . ?
C4 C40 1.510(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N1 C7 1.474(2) . ?
N1 H1A 0.84(3) . ?
C7 C8 1.506(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.391(2) . ?
C8 C13 1.397(2) . ?
C9 C10 1.379(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9300 . ?
C13 N2 1.420(2) . ?
C14 N2 1.284(2) . ?
C14 C15 1.434(2) . ?
C14 H14 0.9300 . ?
C15 C20 1.405(2) . ?
C15 C16 1.407(2) . ?
C20 O3 1.3312(19) . ?
C20 C19 1.408(2) . ?
C19 O4 1.353(2) . ?
C19 C18 1.372(2) . ?
C18 C17 1.389(3) . ?
C18 H18 0.9300 . ?
C17 C16 1.369(3) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C40 H40D 0.9600 . ?
C40 H40E 0.9600 . ?
C40 H40F 0.9600 . ?
N2 H3P' 0.75(6) . ?
O3 H3P 0.93(6) . ?
O4 H4P 0.85(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 120.12(9) . . ?
O2 S1 N1 106.86(10) . . ?
O1 S1 N1 105.97(9) . . ?
O2 S1 C1 107.87(9) . . ?
O1 S1 C1 108.64(9) . . ?
N1 S1 C1 106.65(8) . . ?
C2 C1 C6 118.9(2) . . ?
C2 C1 S1 120.39(15) . . ?
C6 C1 S1 120.46(16) . . ?
C1 C2 C3 119.90(19) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C5 C4 C3 117.7(2) . . ?
C5 C4 C40 120.9(2) . . ?
C3 C4 C40 121.3(2) . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 119.9(2) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C7 N1 S1 117.00(13) . . ?
C7 N1 H1A 118.0(18) . . ?
S1 N1 H1A 110.0(17) . . ?
N1 C7 C8 114.60(14) . . ?
N1 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C13 118.17(15) . . ?
C9 C8 C7 122.62(15) . . ?
C13 C8 C7 119.15(14) . . ?
C10 C9 C8 121.18(17) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 119.99(18) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.25(18) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 120.08(18) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 120.24(16) . . ?
C12 C13 N2 122.05(16) . . ?
C8 C13 N2 117.71(14) . . ?
N2 C14 C15 121.51(15) . . ?
N2 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C20 C15 C16 119.51(15) . . ?
C20 C15 C14 120.37(14) . . ?
C16 C15 C14 120.08(15) . . ?
O3 C20 C15 122.27(15) . . ?
O3 C20 C19 118.56(14) . . ?
C15 C20 C19 119.17(14) . . ?
O4 C19 C18 119.64(16) . . ?
O4 C19 C20 120.34(15) . . ?
C18 C19 C20 120.00(16) . . ?
C19 C18 C17 120.71(17) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C16 C17 C18 120.49(16) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C16 C15 120.10(17) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C4 C40 H40A 109.5 . . ?
C4 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C4 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C4 C40 H40D 109.5 . . ?
C4 C40 H40E 109.5 . . ?
H40D C40 H40E 109.5 . . ?
C4 C40 H40F 109.5 . . ?
H40D C40 H40F 109.5 . . ?
H40E C40 H40F 109.5 . . ?
H3P' N2 C14 117(4) . . ?
H3P' N2 C13 119(4) . . ?
C14 N2 C13 123.96(15) . . ?
H3P O3 C20 101(3) . . ?
C19 O4 H4P 111(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C1 C2 -168.97(18) . . . . ?
O1 S1 C1 C2 -37.3(2) . . . . ?
N1 S1 C1 C2 76.55(19) . . . . ?
O2 S1 C1 C6 16.9(2) . . . . ?
O1 S1 C1 C6 148.61(19) . . . . ?
N1 S1 C1 C6 -97.6(2) . . . . ?
C6 C1 C2 C3 1.3(4) . . . . ?
S1 C1 C2 C3 -172.89(19) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C2 C3 C4 C40 177.0(2) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C40 C4 C5 C6 -177.0(3) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
S1 C1 C6 C5 172.9(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
O2 S1 N1 C7 -56.94(15) . . . . ?
O1 S1 N1 C7 173.86(12) . . . . ?
C1 S1 N1 C7 58.23(14) . . . . ?
S1 N1 C7 C8 98.67(17) . . . . ?
N1 C7 C8 C9 18.5(3) . . . . ?
N1 C7 C8 C13 -164.18(16) . . . . ?
C13 C8 C9 C10 -0.9(3) . . . . ?
C7 C8 C9 C10 176.4(2) . . . . ?
C8 C9 C10 C11 -1.4(4) . . . . ?
C9 C10 C11 C12 1.6(4) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 C8 -2.8(4) . . . . ?
C11 C12 C13 N2 178.1(2) . . . . ?
C9 C8 C13 C12 3.0(3) . . . . ?
C7 C8 C13 C12 -174.4(2) . . . . ?
C9 C8 C13 N2 -177.87(16) . . . . ?
C7 C8 C13 N2 4.7(3) . . . . ?
N2 C14 C15 C20 3.4(3) . . . . ?
N2 C14 C15 C16 -179.07(18) . . . . ?
C16 C15 C20 O3 178.85(18) . . . . ?
C14 C15 C20 O3 -3.6(3) . . . . ?
C16 C15 C20 C19 -1.1(3) . . . . ?
C14 C15 C20 C19 176.42(17) . . . . ?
O3 C20 C19 O4 0.5(3) . . . . ?
C15 C20 C19 O4 -179.58(19) . . . . ?
O3 C20 C19 C18 -178.57(19) . . . . ?
C15 C20 C19 C18 1.4(3) . . . . ?
O4 C19 C18 C17 -179.8(2) . . . . ?
C20 C19 C18 C17 -0.8(3) . . . . ?
C19 C18 C17 C16 -0.2(4) . . . . ?
C18 C17 C16 C15 0.5(3) . . . . ?
C20 C15 C16 C17 0.2(3) . . . . ?
C14 C15 C16 C17 -177.33(19) . . . . ?
C15 C14 N2 H3P' -6(4) . . . . ?
C15 C14 N2 C13 -176.83(16) . . . . ?
C12 C13 N2 H3P' 172(4) . . . . ?
C8 C13 N2 H3P' -8(4) . . . . ?
C12 C13 N2 C14 -18.1(3) . . . . ?
C8 C13 N2 C14 162.72(17) . . . . ?
C15 C20 O3 H3P 0(3) . . . . ?
C19 C20 O3 H3P -180(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14 O2 0.93 2.59 3.492(2) 163.6 2_656
C18 H18 O1 0.93 2.61 3.464(3) 153.1 1_564
N1 H1A O1 0.84(3) 2.28(3) 3.107(2) 170(2) 2_746
O4 H4P O3 0.85(4) 1.98(4) 2.747(2) 150(3) 2_755

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-4


_chemical_properties_physical    Thermocromic
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1402382'
_audit_update_record             
;
2015-05-22 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H28 N4 O3 S'
_chemical_formula_sum            'C25 H28 N4 O3 S'
_chemical_formula_weight         464.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7401(12)
_cell_length_b                   10.3466(13)
_cell_length_c                   12.7780(18)
_cell_angle_alpha                91.204(6)
_cell_angle_beta                 91.180(6)
_cell_angle_gamma                91.168(5)
_cell_volume                     1154.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1972
_cell_measurement_theta_min      2.331
_cell_measurement_theta_max      24.592

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SADABS-2014 (Bruker, 2014)'

_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 X8 KappaAPEXII'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16285
_diffrn_reflns_av_unetI/netI     0.0882
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.594
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             4138
_reflns_number_gt                2668
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'BRUKER APEX2'
_computing_cell_refinement       'BRUKER APEX2'
_computing_data_reduction        ?
_computing_structure_solution    'SIR-2008 (bural, 2008)'
_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)+(0.0831P)²+0.9486P] 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         4138
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.1831
_refine_ls_wR_factor_gt          0.1565
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.19317(11) 0.08901(9) 0.67766(8) 0.0231(3) Uani 1 1 d . . . . .
O1 O 0.2455(3) 0.1771(2) 0.7591(2) 0.0261(6) Uani 1 1 d . . . . .
O2 O 0.1259(3) 0.1370(2) 0.5832(2) 0.0271(6) Uani 1 1 d . . . . .
O3 O -0.2950(3) 0.2595(2) 0.9661(2) 0.0270(6) Uani 1 1 d . . . . .
N1 N 0.0558(3) -0.0012(3) 0.7302(2) 0.0194(7) Uani 1 1 d . . . . .
N2 N 0.1881(3) -0.1482(3) 0.8411(3) 0.0213(7) Uani 1 1 d . . . . .
N3 N -0.3262(3) -0.0117(3) 0.9376(2) 0.0223(7) Uani 1 1 d . . . . .
N4 N -0.1749(4) 0.1339(3) 0.8461(3) 0.0232(8) Uani 1 1 d . . . . .
C1 C 0.3403(4) -0.0156(3) 0.6426(3) 0.0220(9) Uani 1 1 d . . . . .
C2 C 0.3320(4) -0.0791(4) 0.5463(3) 0.0259(9) Uani 1 1 d . . . . .
H2 H 0.2567 -0.0571 0.4954 0.031 Uiso 1 1 calc R U . . .
C3 C 0.4359(4) -0.1760(4) 0.5253(3) 0.0274(9) Uani 1 1 d . . . . .
H3 H 0.4318 -0.2197 0.4592 0.033 Uiso 1 1 calc R U . . .
C4 C 0.5449(4) -0.2095(4) 0.5991(3) 0.0276(9) Uani 1 1 d . . . . .
C40 C 0.6489(5) -0.3214(4) 0.5762(3) 0.0328(10) Uani 1 1 d . . . . .
H40A H 0.5874 -0.4013 0.5675 0.049 Uiso 1 1 calc R U . . .
H40B H 0.7223 -0.3302 0.6345 0.049 Uiso 1 1 calc R U . . .
H40C H 0.7044 -0.3051 0.5118 0.049 Uiso 1 1 calc R U . . .
C5 C 0.5549(4) -0.1414(4) 0.6937(3) 0.0264(9) Uani 1 1 d . . . . .
H5 H 0.6316 -0.1625 0.7439 0.032 Uiso 1 1 calc R U . . .
C6 C 0.4541(4) -0.0424(3) 0.7162(3) 0.0246(9) Uani 1 1 d . . . . .
H6 H 0.4630 0.0057 0.7803 0.030 Uiso 1 1 calc R U . . .
C7 C -0.0075(4) -0.1089(3) 0.6618(3) 0.0212(8) Uani 1 1 d . . . . .
H7A H -0.0009 -0.0841 0.5876 0.025 Uiso 1 1 calc R U . . .
H7B H -0.1168 -0.1236 0.6775 0.025 Uiso 1 1 calc R U . . .
C8 C 0.0783(4) -0.2329(3) 0.6779(3) 0.0211(8) Uani 1 1 d . . . . .
C9 C 0.0694(4) -0.3311(4) 0.6016(3) 0.0263(9) Uani 1 1 d . . . . .
H9 H 0.0081 -0.3199 0.5404 0.032 Uiso 1 1 calc R U . . .
C10 C 0.1484(5) -0.4448(4) 0.6134(3) 0.0308(10) Uani 1 1 d . . . . .
H10 H 0.1416 -0.5112 0.5609 0.037 Uiso 1 1 calc R U . . .
C11 C 0.2369(4) -0.4598(4) 0.7027(3) 0.0294(10) Uani 1 1 d . . . . .
H11 H 0.2900 -0.5382 0.7116 0.035 Uiso 1 1 calc R U . . .
C12 C 0.2506(4) -0.3638(3) 0.7797(3) 0.0273(9) Uani 1 1 d . . . . .
H12 H 0.3139 -0.3753 0.8400 0.033 Uiso 1 1 calc R U . . .
C13 C 0.1688(4) -0.2483(3) 0.7672(3) 0.0215(9) Uani 1 1 d . . . . .
C19 C -0.1934(4) 0.0110(3) 0.8934(3) 0.0213(8) Uani 1 1 d . . . . .
C16 C -0.1018(4) -0.1972(3) 0.9309(3) 0.0218(9) Uani 1 1 d . . . . .
H16 H -0.0258 -0.2615 0.9286 0.026 Uiso 1 1 calc R U . . .
C17 C -0.2390(4) -0.2231(3) 0.9778(3) 0.0243(9) Uani 1 1 d . . . . .
H17 H -0.2583 -0.3048 1.0081 0.029 Uiso 1 1 calc R U . . .
C18 C -0.3484(4) -0.1283(3) 0.9802(3) 0.0229(9) Uani 1 1 d . . . . .
H18 H -0.4428 -0.1462 1.0131 0.027 Uiso 1 1 calc R U . . .
C14 C 0.0808(4) -0.0436(3) 0.8389(3) 0.0199(8) Uani 1 1 d . . . . .
H14 H 0.1273 0.0309 0.8802 0.024 Uiso 1 1 calc R U . . .
C15 C -0.0736(4) -0.0777(3) 0.8868(3) 0.0196(8) Uani 1 1 d . . . . .
C20 C -0.2352(4) 0.2475(3) 0.8807(3) 0.0222(9) Uani 1 1 d . . . . .
C21 C -0.2212(5) 0.3626(4) 0.8075(3) 0.0276(9) Uani 1 1 d . . . . .
C22 C -0.3816(6) 0.4184(5) 0.8001(5) 0.074(2) Uani 1 1 d . . . . .
H22A H -0.4516 0.3549 0.7655 0.111 Uiso 1 1 calc R U . . .
H22B H -0.3785 0.4976 0.7593 0.111 Uiso 1 1 calc R U . . .
H22C H -0.4176 0.4384 0.8706 0.111 Uiso 1 1 calc R U . . .
C23 C -0.1658(5) 0.3291(4) 0.6989(3) 0.0376(11) Uani 1 1 d . . . . .
H23A H -0.0589 0.3024 0.7035 0.056 Uiso 1 1 calc R U . . .
H23B H -0.1733 0.4050 0.6547 0.056 Uiso 1 1 calc R U . . .
H23C H -0.2292 0.2582 0.6684 0.056 Uiso 1 1 calc R U . . .
C24 C -0.1091(7) 0.4594(4) 0.8606(4) 0.0572(15) Uani 1 1 d . . . . .
H24A H -0.1464 0.4836 0.9300 0.086 Uiso 1 1 calc R U . . .
H24B H -0.1003 0.5368 0.8180 0.086 Uiso 1 1 calc R U . . .
H24C H -0.0085 0.4201 0.8681 0.086 Uiso 1 1 calc R U . . .
H4A H -0.120(4) 0.139(4) 0.789(3) 0.020(10) Uiso 1 1 d . . . . .
H2A H 0.237(4) -0.160(4) 0.905(3) 0.027(11) Uiso 1 1 d . . . 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 1.430(3) . ?
S1 O2 1.435(3) . ?
S1 N1 1.666(3) . ?
S1 C1 1.757(4) . ?
O3 C20 1.224(4) . ?
N1 C14 1.479(5) . ?
N1 C7 1.491(4) . ?
N2 C13 1.392(5) . ?
N2 C14 1.447(4) . ?
N2 H2A 0.92(4) . ?
N3 C19 1.320(5) . ?
N3 C18 1.347(4) . ?
N4 C20 1.367(5) . ?
N4 C19 1.427(4) . ?
N4 H4A 0.88(4) . ?
C1 C2 1.382(5) . ?
C1 C6 1.391(5) . ?
C2 C3 1.392(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(6) . ?
C4 C40 1.514(5) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C5 C6 1.394(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.515(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.389(5) . ?
C8 C9 1.393(5) . ?
C9 C10 1.385(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.415(5) . ?
C12 H12 0.9500 . ?
C19 C15 1.410(5) . ?
C16 C17 1.377(5) . ?
C16 C15 1.389(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C14 C15 1.531(5) . ?
C14 H14 1.0000 . ?
C20 C21 1.535(5) . ?
C21 C23 1.514(6) . ?
C21 C24 1.526(6) . ?
C21 C22 1.529(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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 120.12(15) . . ?
O1 S1 N1 105.65(15) . . ?
O2 S1 N1 105.01(15) . . ?
O1 S1 C1 110.25(17) . . ?
O2 S1 C1 107.91(17) . . ?
N1 S1 C1 107.08(16) . . ?
C14 N1 C7 111.3(3) . . ?
C14 N1 S1 117.5(2) . . ?
C7 N1 S1 115.4(2) . . ?
C13 N2 C14 118.1(3) . . ?
C13 N2 H2A 122(2) . . ?
C14 N2 H2A 116(2) . . ?
C19 N3 C18 117.4(3) . . ?
C20 N4 C19 126.0(3) . . ?
C20 N4 H4A 115(2) . . ?
C19 N4 H4A 119(2) . . ?
C2 C1 C6 121.4(3) . . ?
C2 C1 S1 119.1(3) . . ?
C6 C1 S1 119.1(3) . . ?
C1 C2 C3 118.8(4) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 C40 119.5(4) . . ?
C5 C4 C40 121.3(4) . . ?
C4 C40 H40A 109.5 . . ?
C4 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C4 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C4 C5 C6 121.0(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.4(4) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
N1 C7 C8 111.7(3) . . ?
N1 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C13 C8 C9 119.6(3) . . ?
C13 C8 C7 120.4(3) . . ?
C9 C8 C7 119.9(3) . . ?
C10 C9 C8 121.3(4) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 118.7(4) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 121.8(4) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C13 119.0(4) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C8 C13 N2 120.8(3) . . ?
C8 C13 C12 119.6(3) . . ?
N2 C13 C12 119.5(3) . . ?
N3 C19 C15 125.0(3) . . ?
N3 C19 N4 116.2(3) . . ?
C15 C19 N4 118.8(3) . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 118.9(3) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
N3 C18 C17 122.5(3) . . ?
N3 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
N2 C14 N1 110.2(3) . . ?
N2 C14 C15 113.6(3) . . ?
N1 C14 C15 109.4(3) . . ?
N2 C14 H14 107.8 . . ?
N1 C14 H14 107.8 . . ?
C15 C14 H14 107.8 . . ?
C16 C15 C19 115.6(3) . . ?
C16 C15 C14 121.7(3) . . ?
C19 C15 C14 122.6(3) . . ?
O3 C20 N4 122.8(3) . . ?
O3 C20 C21 120.8(3) . . ?
N4 C20 C21 116.4(3) . . ?
C23 C21 C24 109.3(4) . . ?
C23 C21 C22 109.9(4) . . ?
C24 C21 C22 110.8(4) . . ?
C23 C21 C20 114.7(3) . . ?
C24 C21 C20 106.7(3) . . ?
C22 C21 C20 105.4(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C14 -40.5(3) . . . . ?
O2 S1 N1 C14 -168.4(2) . . . . ?
C1 S1 N1 C14 77.0(3) . . . . ?
O1 S1 N1 C7 -174.9(2) . . . . ?
O2 S1 N1 C7 57.2(3) . . . . ?
C1 S1 N1 C7 -57.4(3) . . . . ?
O1 S1 C1 C2 -159.8(3) . . . . ?
O2 S1 C1 C2 -26.9(3) . . . . ?
N1 S1 C1 C2 85.7(3) . . . . ?
O1 S1 C1 C6 26.6(3) . . . . ?
O2 S1 C1 C6 159.5(3) . . . . ?
N1 S1 C1 C6 -87.9(3) . . . . ?
C6 C1 C2 C3 3.0(6) . . . . ?
S1 C1 C2 C3 -170.5(3) . . . . ?
C1 C2 C3 C4 0.6(6) . . . . ?
C2 C3 C4 C5 -3.0(6) . . . . ?
C2 C3 C4 C40 175.9(3) . . . . ?
C3 C4 C5 C6 1.8(6) . . . . ?
C40 C4 C5 C6 -177.0(3) . . . . ?
C2 C1 C6 C5 -4.1(5) . . . . ?
S1 C1 C6 C5 169.4(3) . . . . ?
C4 C5 C6 C1 1.6(5) . . . . ?
C14 N1 C7 C8 -46.2(4) . . . . ?
S1 N1 C7 C8 90.9(3) . . . . ?
N1 C7 C8 C13 18.1(5) . . . . ?
N1 C7 C8 C9 -160.4(3) . . . . ?
C13 C8 C9 C10 0.5(5) . . . . ?
C7 C8 C9 C10 179.0(3) . . . . ?
C8 C9 C10 C11 0.0(6) . . . . ?
C9 C10 C11 C12 -1.0(6) . . . . ?
C10 C11 C12 C13 1.3(6) . . . . ?
C9 C8 C13 N2 175.5(3) . . . . ?
C7 C8 C13 N2 -3.0(5) . . . . ?
C9 C8 C13 C12 -0.1(5) . . . . ?
C7 C8 C13 C12 -178.7(3) . . . . ?
C14 N2 C13 C8 17.2(5) . . . . ?
C14 N2 C13 C12 -167.2(3) . . . . ?
C11 C12 C13 C8 -0.8(5) . . . . ?
C11 C12 C13 N2 -176.4(3) . . . . ?
C18 N3 C19 C15 0.4(6) . . . . ?
C18 N3 C19 N4 178.1(3) . . . . ?
C20 N4 C19 N3 34.2(5) . . . . ?
C20 N4 C19 C15 -148.0(4) . . . . ?
C15 C16 C17 C18 0.1(6) . . . . ?
C19 N3 C18 C17 -0.7(5) . . . . ?
C16 C17 C18 N3 0.5(6) . . . . ?
C13 N2 C14 N1 -45.5(4) . . . . ?
C13 N2 C14 C15 77.6(4) . . . . ?
C7 N1 C14 N2 60.2(4) . . . . ?
S1 N1 C14 N2 -76.0(3) . . . . ?
C7 N1 C14 C15 -65.4(3) . . . . ?
S1 N1 C14 C15 158.5(2) . . . . ?
C17 C16 C15 C19 -0.4(5) . . . . ?
C17 C16 C15 C14 176.9(3) . . . . ?
N3 C19 C15 C16 0.1(6) . . . . ?
N4 C19 C15 C16 -177.5(3) . . . . ?
N3 C19 C15 C14 -177.1(3) . . . . ?
N4 C19 C15 C14 5.2(5) . . . . ?
N2 C14 C15 C16 2.2(5) . . . . ?
N1 C14 C15 C16 125.7(4) . . . . ?
N2 C14 C15 C19 179.2(3) . . . . ?
N1 C14 C15 C19 -57.2(4) . . . . ?
C19 N4 C20 O3 10.8(6) . . . . ?
C19 N4 C20 C21 -170.6(3) . . . . ?
O3 C20 C21 C23 -171.7(4) . . . . ?
N4 C20 C21 C23 9.7(5) . . . . ?
O3 C20 C21 C24 67.1(5) . . . . ?
N4 C20 C21 C24 -111.5(4) . . . . ?
O3 C20 C21 C22 -50.7(5) . . . . ?
N4 C20 C21 C22 130.7(4) . . . . ?

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
C7 H7A O2 0.99 2.47 3.282(4) 139.4 2_556
C18 H18 O3 0.95 2.57 3.461(4) 155.6 2_457
C18 H18 N3 0.95 2.70 3.393(5) 130.4 2_457
N4 H4A N1 0.88(4) 2.26(4) 2.892(4) 128(3) .
N2 H2A O3 0.92(4) 2.02(4) 2.887(4) 155(3) 2_557

_refine_diff_density_max         0.389
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.086

_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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1402383'
_audit_update_record             
;
2015-05-22 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H28 N4 O3 S, C H Cl3'
_chemical_formula_sum            'C26 H29 Cl3 N4 O3 S'
_chemical_formula_weight         583.94

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0744(8)
_cell_length_b                   11.5179(8)
_cell_length_c                   13.2903(9)
_cell_angle_alpha                64.902(4)
_cell_angle_beta                 84.007(5)
_cell_angle_gamma                87.326(5)
_cell_volume                     1388.91(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1977
_cell_measurement_theta_min      2.714
_cell_measurement_theta_max      25.686

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.440
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.801
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_process_details   'SABABS-2014 (Bruker 2014)'

_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 X8 KappaAPEXII'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_reflns_number            29871
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.699
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5483
_reflns_number_gt                4105
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'BRUKER APEX2'
_computing_cell_refinement       'BRUKER APEX2'
_computing_data_reduction        ?
_computing_structure_solution    'SIR-2008 (Burla., 2008)'
_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)+(0.0542P)²+1.1269P] 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         5483
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
H4A H 0.368(3) 0.266(3) 0.877(2) 0.015(7) Uiso 1 1 d . . . . .
H2A H 0.688(3) 0.010(3) 0.813(2) 0.025(8) Uiso 1 1 d . . . . .
S1 S 0.44061(6) 0.25213(6) 0.63672(5) 0.01805(15) Uani 1 1 d . . . . .
O1 O 0.34633(16) 0.14945(16) 0.69012(14) 0.0224(4) Uani 1 1 d . . . . .
O2 O 0.39438(18) 0.37996(16) 0.57433(14) 0.0242(4) Uani 1 1 d . . . . .
C1 C 0.5601(2) 0.2121(2) 0.55035(19) 0.0176(5) Uani 1 1 d . . . . .
C2 C 0.6421(2) 0.3070(2) 0.4700(2) 0.0202(5) Uani 1 1 d . . . . .
H2 H 0.6304 0.3939 0.4585 0.024 Uiso 1 1 calc R U . . .
C3 C 0.7414(3) 0.2731(2) 0.4070(2) 0.0236(6) Uani 1 1 d . . . . .
H3 H 0.7982 0.3376 0.3524 0.028 Uiso 1 1 calc R U . . .
C4 C 0.7594(3) 0.1462(2) 0.4223(2) 0.0238(6) Uani 1 1 d . . . . .
C40 C 0.8674(3) 0.1097(3) 0.3542(3) 0.0372(7) Uani 1 1 d . . . . .
H40A H 0.9402 0.0669 0.4003 0.056 Uiso 1 1 calc R U . . .
H40B H 0.9016 0.1870 0.2901 0.056 Uiso 1 1 calc R U . . .
H40C H 0.8311 0.0514 0.3276 0.056 Uiso 1 1 calc R U . . .
C5 C 0.6748(3) 0.0531(2) 0.5030(2) 0.0245(6) Uani 1 1 d . . . . .
H5 H 0.6855 -0.0338 0.5141 0.029 Uiso 1 1 calc R U . . .
C6 C 0.5761(2) 0.0846(2) 0.5669(2) 0.0209(5) Uani 1 1 d . . . . .
H6 H 0.5195 0.0201 0.6218 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6255(2) 0.3540(2) 0.7064(2) 0.0183(5) Uani 1 1 d . . . . .
H7A H 0.6289 0.3846 0.7653 0.022 Uiso 1 1 calc R U . . .
H7B H 0.6055 0.4286 0.6370 0.022 Uiso 1 1 calc R U . . .
N1 N 0.51662(19) 0.25835(17) 0.74006(16) 0.0160(4) Uani 1 1 d . . . . .
C8 C 0.7597(2) 0.2992(2) 0.68733(19) 0.0166(5) Uani 1 1 d . . . . .
C9 C 0.8675(3) 0.3793(2) 0.6319(2) 0.0225(6) Uani 1 1 d . . . . .
H9 H 0.8569 0.4691 0.6085 0.027 Uiso 1 1 calc R U . . .
C10 C 0.9897(3) 0.3317(3) 0.6098(2) 0.0270(6) Uani 1 1 d . . . . .
H10 H 1.0629 0.3880 0.5729 0.032 Uiso 1 1 calc R U . . .
C11 C 1.0048(3) 0.2002(3) 0.6421(2) 0.0253(6) Uani 1 1 d . . . . .
H11 H 1.0878 0.1670 0.6248 0.030 Uiso 1 1 calc R U . . .
C12 C 0.8999(2) 0.1179(2) 0.6991(2) 0.0203(5) Uani 1 1 d . . . . .
H12 H 0.9113 0.0283 0.7216 0.024 Uiso 1 1 calc R U . . .
C13 C 0.7769(2) 0.1660(2) 0.72402(19) 0.0160(5) Uani 1 1 d . . . . .
N2 N 0.6701(2) 0.0840(2) 0.77994(17) 0.0161(4) Uani 1 1 d . . . . .
C14 C 0.5577(2) 0.1321(2) 0.82612(19) 0.0150(5) Uani 1 1 d . . . . .
H14 H 0.4821 0.0707 0.8458 0.018 Uiso 1 1 calc R U . . .
C15 C 0.5833(2) 0.1481(2) 0.93116(19) 0.0156(5) Uani 1 1 d . . . . .
C16 C 0.7024(2) 0.1092(2) 0.9788(2) 0.0172(5) Uani 1 1 d . . . . .
H16 H 0.7723 0.0777 0.9434 0.021 Uiso 1 1 calc R U . . .
C17 C 0.7202(2) 0.1159(2) 1.0782(2) 0.0205(5) Uani 1 1 d . . . . .
H17 H 0.8013 0.0885 1.1121 0.025 Uiso 1 1 calc R U . . .
C18 C 0.6169(2) 0.1636(2) 1.1268(2) 0.0199(5) Uani 1 1 d . . . . .
H18 H 0.6291 0.1686 1.1948 0.024 Uiso 1 1 calc R U . . .
N3 N 0.5004(2) 0.20327(18) 1.08290(16) 0.0178(4) Uani 1 1 d . . . . .
C19 C 0.4845(2) 0.1950(2) 0.98771(19) 0.0156(5) Uani 1 1 d . . . . .
N4 N 0.3629(2) 0.2393(2) 0.94152(19) 0.0178(4) Uani 1 1 d . . . . .
C20 C 0.2398(2) 0.2301(2) 0.9982(2) 0.0166(5) Uani 1 1 d . . . . .
O3 O 0.22138(16) 0.17050(15) 1.09997(14) 0.0193(4) Uani 1 1 d . . . . .
C21 C 0.1242(2) 0.2917(2) 0.9278(2) 0.0196(5) Uani 1 1 d . . . . .
C22 C 0.1665(3) 0.4076(3) 0.8190(2) 0.0337(7) Uani 1 1 d . . . . .
H22A H 0.2134 0.4691 0.8356 0.051 Uiso 1 1 calc R U . . .
H22B H 0.0872 0.4486 0.7812 0.051 Uiso 1 1 calc R U . . .
H22C H 0.2259 0.3793 0.7705 0.051 Uiso 1 1 calc R U . . .
C23 C 0.0656(3) 0.1876(2) 0.9020(2) 0.0253(6) Uani 1 1 d . . . . .
H23A H -0.0131 0.2215 0.8609 0.038 Uiso 1 1 calc R U . . .
H23B H 0.0399 0.1132 0.9720 0.038 Uiso 1 1 calc R U . . .
H23C H 0.1327 0.1615 0.8567 0.038 Uiso 1 1 calc R U . . .
C24 C 0.0197(3) 0.3338(3) 0.9979(2) 0.0302(6) Uani 1 1 d . . . . .
H24A H 0.0574 0.4005 1.0138 0.045 Uiso 1 1 calc R U . . .
H24B H -0.0064 0.2600 1.0683 0.045 Uiso 1 1 calc R U . . .
H24C H -0.0589 0.3678 0.9567 0.045 Uiso 1 1 calc R U . . .
C1S C 0.6876(3) 0.6570(3) 0.7945(2) 0.0310(6) Uani 1 1 d . . . . .
H1S H 0.6828 0.7289 0.8180 0.037 Uiso 1 1 calc R U . . .
Cl1 Cl 0.55853(9) 0.67599(8) 0.70971(7) 0.0465(2) Uani 1 1 d . . . . .
Cl2 Cl 0.67077(8) 0.51107(7) 0.91459(7) 0.0429(2) Uani 1 1 d . . . . .
Cl3 Cl 0.84307(9) 0.66258(10) 0.71894(9) 0.0625(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
S1 O2 1.4330(17) . ?
S1 O1 1.4340(18) . ?
S1 N1 1.669(2) . ?
S1 C1 1.757(2) . ?
C1 C2 1.388(3) . ?
C1 C6 1.394(3) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(4) . ?
C4 C40 1.501(4) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C5 C6 1.376(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.486(3) . ?
C7 C8 1.509(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
N1 C14 1.492(3) . ?
C8 C9 1.386(3) . ?
C8 C13 1.407(3) . ?
C9 C10 1.379(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.399(3) . ?
C12 H12 0.9500 . ?
C13 N2 1.391(3) . ?
N2 C14 1.432(3) . ?
N2 H2A 0.80(3) . ?
C14 C15 1.532(3) . ?
C14 H14 1.0000 . ?
C15 C16 1.382(3) . ?
C15 C19 1.409(3) . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 N3 1.339(3) . ?
C18 H18 0.9500 . ?
N3 C19 1.335(3) . ?
C19 N4 1.404(3) . ?
N4 C20 1.366(3) . ?
N4 H4A 0.77(3) . ?
C20 O3 1.228(3) . ?
C20 C21 1.524(3) . ?
C21 C22 1.530(3) . ?
C21 C24 1.530(3) . ?
C21 C23 1.537(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C1S Cl1 1.754(3) . ?
C1S Cl3 1.758(3) . ?
C1S Cl2 1.759(3) . ?
C1S H1S 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.76(11) . . ?
O2 S1 N1 105.51(10) . . ?
O1 S1 N1 105.25(10) . . ?
O2 S1 C1 108.48(11) . . ?
O1 S1 C1 108.97(11) . . ?
N1 S1 C1 108.33(10) . . ?
C2 C1 C6 120.7(2) . . ?
C2 C1 S1 119.56(18) . . ?
C6 C1 S1 119.68(19) . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 C40 121.1(2) . . ?
C5 C4 C40 120.5(2) . . ?
C4 C40 H40A 109.5 . . ?
C4 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C4 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 119.3(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N1 C7 C8 112.21(18) . . ?
N1 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 N1 C14 110.91(18) . . ?
C7 N1 S1 116.24(15) . . ?
C14 N1 S1 115.49(15) . . ?
C9 C8 C13 118.9(2) . . ?
C9 C8 C7 120.6(2) . . ?
C13 C8 C7 120.4(2) . . ?
C10 C9 C8 121.6(2) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 119.3(2) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
N2 C13 C12 120.6(2) . . ?
N2 C13 C8 119.9(2) . . ?
C12 C13 C8 119.4(2) . . ?
C13 N2 C14 118.33(19) . . ?
C13 N2 H2A 117(2) . . ?
C14 N2 H2A 116(2) . . ?
N2 C14 N1 109.22(18) . . ?
N2 C14 C15 113.99(19) . . ?
N1 C14 C15 108.90(17) . . ?
N2 C14 H14 108.2 . . ?
N1 C14 H14 108.2 . . ?
C15 C14 H14 108.2 . . ?
C16 C15 C19 116.8(2) . . ?
C16 C15 C14 121.0(2) . . ?
C19 C15 C14 122.0(2) . . ?
C15 C16 C17 120.3(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 118.3(2) . . ?
C18 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
N3 C18 C17 123.3(2) . . ?
N3 C18 H18 118.4 . . ?
C17 C18 H18 118.4 . . ?
C19 N3 C18 117.6(2) . . ?
N3 C19 N4 116.9(2) . . ?
N3 C19 C15 123.7(2) . . ?
N4 C19 C15 119.3(2) . . ?
C20 N4 C19 127.0(2) . . ?
C20 N4 H4A 118(2) . . ?
C19 N4 H4A 114(2) . . ?
O3 C20 N4 122.1(2) . . ?
O3 C20 C21 121.3(2) . . ?
N4 C20 C21 116.5(2) . . ?
C20 C21 C22 113.1(2) . . ?
C20 C21 C24 107.9(2) . . ?
C22 C21 C24 109.3(2) . . ?
C20 C21 C23 106.70(19) . . ?
C22 C21 C23 109.9(2) . . ?
C24 C21 C23 109.8(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
Cl1 C1S Cl3 109.94(16) . . ?
Cl1 C1S Cl2 110.71(16) . . ?
Cl3 C1S Cl2 110.08(15) . . ?
Cl1 C1S H1S 108.7 . . ?
Cl3 C1S H1S 108.7 . . ?
Cl2 C1S H1S 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C1 C2 32.6(2) . . . . ?
O1 S1 C1 C2 164.52(18) . . . . ?
N1 S1 C1 C2 -81.5(2) . . . . ?
O2 S1 C1 C6 -150.64(19) . . . . ?
O1 S1 C1 C6 -18.7(2) . . . . ?
N1 S1 C1 C6 95.3(2) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
S1 C1 C2 C3 176.11(18) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C2 C3 C4 C40 -179.7(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C40 C4 C5 C6 179.4(3) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
S1 C1 C6 C5 -176.47(19) . . . . ?
C8 C7 N1 C14 44.5(2) . . . . ?
C8 C7 N1 S1 -90.1(2) . . . . ?
O2 S1 N1 C7 -55.38(18) . . . . ?
O1 S1 N1 C7 177.06(15) . . . . ?
C1 S1 N1 C7 60.62(18) . . . . ?
O2 S1 N1 C14 172.11(15) . . . . ?
O1 S1 N1 C14 44.55(18) . . . . ?
C1 S1 N1 C14 -71.89(18) . . . . ?
N1 C7 C8 C9 165.3(2) . . . . ?
N1 C7 C8 C13 -13.6(3) . . . . ?
C13 C8 C9 C10 1.4(4) . . . . ?
C7 C8 C9 C10 -177.5(2) . . . . ?
C8 C9 C10 C11 1.2(4) . . . . ?
C9 C10 C11 C12 -2.3(4) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C11 C12 C13 N2 179.0(2) . . . . ?
C11 C12 C13 C8 2.0(4) . . . . ?
C9 C8 C13 N2 179.9(2) . . . . ?
C7 C8 C13 N2 -1.1(3) . . . . ?
C9 C8 C13 C12 -3.0(3) . . . . ?
C7 C8 C13 C12 175.9(2) . . . . ?
C12 C13 N2 C14 165.7(2) . . . . ?
C8 C13 N2 C14 -17.3(3) . . . . ?
C13 N2 C14 N1 48.4(3) . . . . ?
C13 N2 C14 C15 -73.6(3) . . . . ?
C7 N1 C14 N2 -62.0(2) . . . . ?
S1 N1 C14 N2 72.9(2) . . . . ?
C7 N1 C14 C15 63.0(2) . . . . ?
S1 N1 C14 C15 -162.01(15) . . . . ?
N2 C14 C15 C16 -4.6(3) . . . . ?
N1 C14 C15 C16 -126.8(2) . . . . ?
N2 C14 C15 C19 179.7(2) . . . . ?
N1 C14 C15 C19 57.4(3) . . . . ?
C19 C15 C16 C17 0.6(3) . . . . ?
C14 C15 C16 C17 -175.4(2) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C16 C17 C18 N3 0.2(4) . . . . ?
C17 C18 N3 C19 0.4(3) . . . . ?
C18 N3 C19 N4 -178.7(2) . . . . ?
C18 N3 C19 C15 -0.5(3) . . . . ?
C16 C15 C19 N3 0.0(3) . . . . ?
C14 C15 C19 N3 176.0(2) . . . . ?
C16 C15 C19 N4 178.2(2) . . . . ?
C14 C15 C19 N4 -5.9(3) . . . . ?
N3 C19 N4 C20 -35.6(3) . . . . ?
C15 C19 N4 C20 146.1(2) . . . . ?
C19 N4 C20 O3 -5.9(4) . . . . ?
C19 N4 C20 C21 177.3(2) . . . . ?
O3 C20 C21 C22 153.3(2) . . . . ?
N4 C20 C21 C22 -29.9(3) . . . . ?
O3 C20 C21 C24 32.2(3) . . . . ?
N4 C20 C21 C24 -150.9(2) . . . . ?
O3 C20 C21 C23 -85.7(3) . . . . ?
N4 C20 C21 C23 91.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O3 0.80(3) 2.12(3) 2.904(3) 167(3) 2_657
C2 H2 O2 0.95 2.46 3.406(3) 178.5 2_666
C7 H7A Cl2 0.99 2.99 3.965(2) 170.2 .
C1S H1S O3 1.00 2.20 3.092(3) 147.2 2_667

_refine_diff_density_max         0.568
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-4

