# 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_p093
_database_code_depnum_ccdc_archive 'CCDC 1494732'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;
_audit_creation_date             2016-06-22
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 N2 O2 S'
_chemical_formula_sum            'C15 H20 N2 O2 S'
_chemical_formula_weight         292.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H20 N2 O2 S'
_chemical_oxdiff_usercomment     'Meyer_Koenig_AM-1267 (AM-III-019),F.1.2'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2192(2)
_cell_length_b                   9.1506(2)
_cell_length_c                   13.4968(3)
_cell_angle_alpha                98.630(2)
_cell_angle_beta                 96.960(3)
_cell_angle_gamma                92.679(3)
_cell_volume                     752.15(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6786
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.3320
_cell_measurement_theta_min      5.4570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.937
_exptl_absorpt_correction_T_max  0.875
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.42b (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             312
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 9 0.0858
0 1 -9 0.1022
4 1 1 0.1263
-3 0 -4 0.1370
-4 -1 1 0.1289
-1 -6 4 0.0970
-3 3 -3 0.1207
4 -1 2 0.1154
-4 -1 0 0.1220
0 4 5 0.1110
0 0 -9 0.1003
-1 -5 -3 0.0917
4 -1 -1 0.1017
-3 4 3 0.0858
0 5 3 0.1011
1 -4 -6 0.1065
0 5 -5 0.0840
1 6 -1 0.0840
-1 6 -1 0.0742

_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.188
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0010 -1.0048 9.0009 0.0118 -1.0218 0.1650
-0.0010 1.0048 -9.0009 -0.0118 1.0218 -0.1650
4.0006 1.0009 0.9998 -0.0245 -0.0687 1.0477
-3.0007 0.0010 -3.9999 -0.0506 0.4225 -0.8305
-4.0003 -1.0020 1.0006 -0.0099 -0.1572 -1.0025
-1.0010 -6.0018 3.9968 0.8891 -0.4933 -0.3852
-2.9998 3.0000 -2.9976 -0.5665 0.3255 -0.6935
4.0002 -0.9994 1.9986 0.2909 -0.1922 0.9940
-4.0005 -1.0015 0.0004 0.0073 -0.0443 -1.0251
0.0017 3.9967 5.0037 -0.7508 -0.5436 0.2653
-0.0013 0.0049 -9.0016 0.1544 1.0165 -0.2031
-1.0017 -4.9981 -3.0038 0.8430 0.3026 -0.5051
3.9998 -0.9977 -1.0020 0.3424 0.1466 0.9263
-2.9987 3.9966 3.0042 -0.8357 -0.3469 -0.5200
0.0017 4.9977 3.0041 -0.8827 -0.3124 0.2583
0.9982 -3.9958 -6.0042 0.8077 0.6662 -0.0412
0.0006 5.0020 -4.9974 -0.7455 0.5912 0.0778
1.0014 6.0001 -0.9962 -0.9406 0.1544 0.4529
-0.9987 5.9993 -0.9957 -1.0201 0.1349 -0.0405

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9320
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         73.448
_diffrn_reflns_theta_min         3.340
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -11.00   1.00    1.00    --  -40.71 -57.00-150.00  104
  2  ω    -70.00  33.00   1.00    1.00    --  -40.71  57.00   0.00  103
  3  ω    -20.00  83.00   1.00    1.00    --   40.71 -99.00 120.00  103
  4  ω     32.00  77.00   1.00    2.00    --  106.98 -45.00  60.00   45
  5  ω     32.00  77.00   1.00    2.00    --  106.98 -45.00 -30.00   45
  6  ω     76.00 158.00   1.00    2.00    --  106.98  30.00-180.00   82
  7  ω     32.00 121.00   1.00    2.00    --  106.98-125.00-120.00   89
  8  ω     23.00 109.00   1.00    2.00    --  106.98 -94.00 -30.00   86
  9  ω     23.00 109.00   1.00    2.00    --  106.98 -94.00  60.00   86
 10  ω     23.00 109.00   1.00    2.00    --  106.98 -94.00 -90.00   86
 11  ω     46.00 158.00   1.00    2.00    --  106.98  15.00 -60.00  112
 12  ω     29.00  69.00   1.00    2.00    --  106.98 -30.00 -60.00   40
 13  ω     23.00 109.00   1.00    2.00    --  106.98 -94.00 150.00   86
 14  ω     29.00  69.00   1.00    2.00    --  106.98 -30.00  30.00   40
 15  ω     29.00  69.00   1.00    2.00    --  106.98 -30.00 -90.00   40
 16  ω     29.00  69.00   1.00    2.00    --  106.98 -30.00   0.00   40
 17  ω    -67.00  35.00   1.00    1.00    --  -40.71  37.00 -90.00  102
 18  ω   -119.00  -7.00   1.00    1.00    --  -40.71 -77.00 -30.00  112
 19  ω   -115.00 -11.00   1.00    1.00    --  -40.71 -57.00  30.00  104
 20  ω   -115.00 -11.00   1.00    1.00    --  -40.71 -57.00 120.00  104
 21  ω     77.00 158.00   1.00    2.00    --  106.98  61.00  90.00   81
 22  ω     73.00 158.00   1.00    2.00    --  106.98  77.00 -60.00   85
 23  ω     46.00 158.00   1.00    2.00    --  106.98  15.00  60.00  112
 24  ω     73.00 158.00   1.00    2.00    --  106.98  77.00   0.00   85
 25  ω     73.00 158.00   1.00    2.00    --  106.98  77.00-180.00   85
 26  ω     77.00 113.00   1.00    2.00    --  106.98  61.00 120.00   36
 27  ω     77.00 158.00   1.00    2.00    --  106.98  61.00  60.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0398002000
_diffrn_orient_matrix_UB_12      -0.1662747000
_diffrn_orient_matrix_UB_13      -0.0172522000
_diffrn_orient_matrix_UB_21      0.0097122000
_diffrn_orient_matrix_UB_22      0.0053684000
_diffrn_orient_matrix_UB_23      -0.1129205000
_diffrn_orient_matrix_UB_31      0.2467190000
_diffrn_orient_matrix_UB_32      0.0380544000
_diffrn_orient_matrix_UB_33      0.0225482000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2853
_reflns_number_total             2944
_reflns_odcompleteness_completeness 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2944
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0348P)²+0.3698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0764
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C6(H6), C7(H7), C15(H15), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.32202(5) 0.56038(3) 0.82203(2) 0.01888(10) Uani 1 1 d . . . . .
O1 O 0.24737(15) 0.66949(10) 0.76190(7) 0.0263(2) Uani 1 1 d . . . . .
O2 O 0.17200(15) 0.48815(10) 0.87492(7) 0.0263(2) Uani 1 1 d . . . . .
N2 N 0.33567(18) 0.17536(12) 0.77002(8) 0.0216(2) Uani 1 1 d . . . . .
N1 N 0.41562(17) 0.42809(11) 0.74505(8) 0.0186(2) Uani 1 1 d . . . . .
C10 C 0.4441(2) 0.35479(14) 0.56463(9) 0.0202(3) Uani 1 1 d . . . . .
C4 C 0.4762(2) 0.29967(13) 0.78541(9) 0.0182(2) Uani 1 1 d . . . . .
C2 C 0.7226(2) 0.71741(14) 0.86798(10) 0.0215(3) Uani 1 1 d . . . . .
H2A H 0.6633 0.7909 0.8294 0.026 Uiso 1 1 calc R . . . .
H2B H 0.7869 0.6446 0.8226 0.026 Uiso 1 1 calc R . . . .
C5 C 0.6657(2) 0.27098(14) 0.83968(10) 0.0219(3) Uani 1 1 d . . . . .
H5 H 0.7879 0.3359 0.8603 0.026 Uiso 1 1 calc R . . . .
C3 C 0.5419(2) 0.64218(14) 0.91230(9) 0.0214(3) Uani 1 1 d . . . . .
H3A H 0.4868 0.7148 0.9613 0.026 Uiso 1 1 calc R . . . .
H3B H 0.6024 0.5661 0.9480 0.026 Uiso 1 1 calc R . . . .
C9 C 0.5240(2) 0.46385(14) 0.65874(9) 0.0210(3) Uani 1 1 d . . . . .
H9A H 0.6799 0.4605 0.6747 0.025 Uiso 1 1 calc R . . . .
H9B H 0.4938 0.5633 0.6470 0.025 Uiso 1 1 calc R . . . .
C11 C 0.5792(2) 0.25155(15) 0.52468(10) 0.0281(3) Uani 1 1 d . . . . .
H11 H 0.7197 0.2485 0.5567 0.034 Uiso 1 1 calc R . . . .
C6 C 0.6402(2) 0.12351(15) 0.85851(10) 0.0262(3) Uani 1 1 d . . . . .
H6 H 0.7427 0.0734 0.8939 0.031 Uiso 1 1 calc R . . . .
C8 C 0.1199(2) 0.15781(16) 0.71327(12) 0.0315(3) Uani 1 1 d . . . . .
H8A H 0.0588 0.2525 0.7161 0.047 Uiso 1 1 calc GR . . . .
H8B H 0.0294 0.0920 0.7420 0.047 Uiso 1 1 calc GR . . . .
H8C H 0.1289 0.1173 0.6441 0.047 Uiso 1 1 calc GR . . . .
C7 C 0.4364(2) 0.06822(14) 0.81494(10) 0.0256(3) Uani 1 1 d . . . . .
H7 H 0.3767 -0.0266 0.8158 0.031 Uiso 1 1 calc R . . . .
C15 C 0.2341(2) 0.35729(17) 0.51659(10) 0.0290(3) Uani 1 1 d . . . . .
H15 H 0.1417 0.4257 0.5429 0.035 Uiso 1 1 calc R . . . .
C1 C 0.8962(2) 0.79192(15) 0.95216(11) 0.0278(3) Uani 1 1 d . . . . .
H1A H 1.0082 0.8405 0.9234 0.042 Uiso 1 1 calc GR . . . .
H1B H 0.9577 0.7186 0.9890 0.042 Uiso 1 1 calc GR . . . .
H1C H 0.8321 0.8636 0.9971 0.042 Uiso 1 1 calc GR . . . .
C12 C 0.5066(3) 0.15254(17) 0.43728(12) 0.0378(4) Uani 1 1 d . . . . .
H12 H 0.5986 0.0840 0.4107 0.045 Uiso 1 1 calc R . . . .
C13 C 0.2993(3) 0.15570(18) 0.39011(11) 0.0407(4) Uani 1 1 d . . . . .
H13 H 0.2509 0.0891 0.3317 0.049 Uiso 1 1 calc R . . . .
C14 C 0.1614(3) 0.2578(2) 0.42918(11) 0.0397(4) Uani 1 1 d . . . . .
H14 H 0.0208 0.2597 0.3971 0.048 Uiso 1 1 calc R . . . .


_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 1.4374(9) . ?
S1 O2 1.4361(10) . ?
S1 N1 1.6488(10) . ?
S1 C3 1.7724(13) . ?
N2 C4 1.3760(16) . ?
N2 C8 1.4514(18) . ?
N2 C7 1.3657(17) . ?
N1 C4 1.4154(16) . ?
N1 C9 1.4841(15) . ?
C10 C9 1.5088(17) . ?
C10 C11 1.3858(19) . ?
C10 C15 1.3891(19) . ?
C4 C5 1.3679(18) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.5196(18) . ?
C2 C1 1.5241(18) . ?
C5 H5 0.9300 . ?
C5 C6 1.4154(18) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 H11 0.9300 . ?
C11 C12 1.389(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.370(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.391(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C13 1.370(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(3) . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 106.73(5) . . ?
O1 S1 C3 108.59(6) . . ?
O2 S1 O1 119.48(6) . . ?
O2 S1 N1 106.20(5) . . ?
O2 S1 C3 107.51(6) . . ?
N1 S1 C3 107.83(6) . . ?
C4 N2 C8 126.43(11) . . ?
C7 N2 C4 108.22(11) . . ?
C7 N2 C8 125.32(11) . . ?
C4 N1 S1 116.85(8) . . ?
C4 N1 C9 117.11(10) . . ?
C9 N1 S1 120.50(8) . . ?
C11 C10 C9 120.58(12) . . ?
C11 C10 C15 119.15(13) . . ?
C15 C10 C9 120.27(12) . . ?
N2 C4 N1 120.54(11) . . ?
C5 C4 N2 108.83(11) . . ?
C5 C4 N1 130.61(12) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C3 C2 C1 110.21(11) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C4 C5 H5 126.6 . . ?
C4 C5 C6 106.87(12) . . ?
C6 C5 H5 126.6 . . ?
S1 C3 H3A 108.6 . . ?
S1 C3 H3B 108.6 . . ?
C2 C3 S1 114.44(9) . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
N1 C9 C10 110.36(10) . . ?
N1 C9 H9A 109.6 . . ?
N1 C9 H9B 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.54(14) . . ?
C12 C11 H11 119.7 . . ?
C5 C6 H6 126.3 . . ?
C7 C6 C5 107.36(12) . . ?
C7 C6 H6 126.3 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C7 C6 108.72(12) . . ?
N2 C7 H7 125.6 . . ?
C6 C7 H7 125.6 . . ?
C10 C15 H15 119.9 . . ?
C10 C15 C14 120.22(14) . . ?
C14 C15 H15 119.9 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.05(15) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.24(14) . . ?
C14 C13 H13 119.9 . . ?
C15 C14 H14 120.1 . . ?
C13 C14 C15 119.80(15) . . ?
C13 C14 H14 120.1 . . ?

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
S1 N1 C4 N2 97.72(12) . . . . ?
S1 N1 C4 C5 -84.07(15) . . . . ?
S1 N1 C9 C10 -135.74(10) . . . . ?
O1 S1 N1 C4 -173.13(9) . . . . ?
O1 S1 N1 C9 33.87(11) . . . . ?
O1 S1 C3 C2 -52.33(11) . . . . ?
O2 S1 N1 C4 -44.63(11) . . . . ?
O2 S1 N1 C9 162.36(9) . . . . ?
O2 S1 C3 C2 177.09(9) . . . . ?
N2 C4 C5 C6 -0.14(14) . . . . ?
N1 S1 C3 C2 62.96(10) . . . . ?
N1 C4 C5 C6 -178.51(12) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C10 C15 C14 C13 0.1(2) . . . . ?
C4 N2 C7 C6 -0.15(14) . . . . ?
C4 N1 C9 C10 71.32(14) . . . . ?
C4 C5 C6 C7 0.05(15) . . . . ?
C5 C6 C7 N2 0.06(15) . . . . ?
C3 S1 N1 C4 70.36(10) . . . . ?
C3 S1 N1 C9 -82.64(10) . . . . ?
C9 N1 C4 N2 -108.34(13) . . . . ?
C9 N1 C4 C5 69.87(17) . . . . ?
C9 C10 C11 C12 -179.12(12) . . . . ?
C9 C10 C15 C14 179.28(12) . . . . ?
C11 C10 C9 N1 -109.80(13) . . . . ?
C11 C10 C15 C14 -0.4(2) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C8 N2 C4 N1 0.58(19) . . . . ?
C8 N2 C4 C5 -177.98(12) . . . . ?
C8 N2 C7 C6 178.04(12) . . . . ?
C7 N2 C4 N1 178.75(10) . . . . ?
C7 N2 C4 C5 0.18(14) . . . . ?
C15 C10 C9 N1 70.56(15) . . . . ?
C15 C10 C11 C12 0.5(2) . . . . ?
C1 C2 C3 S1 176.54(9) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-06-22
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.380
_oxdiff_exptl_absorpt_empirical_full_min 0.816
####################################################################### 
# 
# 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_p094
_database_code_depnum_ccdc_archive 'CCDC 1494733'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;
_audit_creation_date             2016-06-27
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H24 N2 O2 S'
_chemical_formula_sum            'C18 H24 N2 O2 S'
_chemical_formula_weight         332.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H24 N2 O2 S'
_chemical_oxdiff_usercomment     Meyer_Koenig_AM-1274(AM-III-026)
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.79743(16)
_cell_length_b                   13.38129(20)
_cell_length_c                   11.85342(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.5156(12)
_cell_angle_gamma                90
_cell_volume                     1701.56(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8875
_cell_measurement_temperature    123.02(10)
_cell_measurement_theta_max      76.2670
_cell_measurement_theta_min      4.9590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.777
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.42b (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -7 4 0.0695
1 -1 8 0.0821
-2 -2 -7 0.0869
4 7 0 0.0712
0 9 -1 0.0269
0 -9 0 0.0812
5 0 5 0.0707
-1 9 -1 0.0223
-1 -6 -6 0.0962
-5 -2 -5 0.0759
3 3 -7 0.0886
5 5 -4 0.0800
-5 5 -2 0.0610
0 -8 -2 0.0802
6 -3 2 0.0986
-6 0 -2 0.0812
-4 7 1 0.0503
-6 0 4 0.0831
3 -7 -2 0.0726
-3 5 6 0.0755
0 7 -4 0.0415

_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.112
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.0000 -7.0000 4.0000 -0.1918 0.8491 -0.5483
1.0000 -1.0000 8.0000 -0.2266 0.9160 0.5216
-2.0000 -2.0000 -7.0000 0.1164 -0.6430 -0.7790
4.0000 7.0000 0.0000 0.0587 -0.4290 0.8907
-0.0000 9.0000 -1.0000 0.6547 -0.4894 0.6504
0.0000 -9.0000 -0.0000 -0.6494 0.3759 -0.7151
5.0000 0.0000 5.0000 -0.5847 0.3969 0.7416
-1.0000 9.0000 -1.0000 0.7663 -0.4553 0.5668
-1.0000 -6.0000 -6.0000 -0.2891 -0.3966 -0.9485
-5.0000 -2.0000 -5.0000 0.4404 -0.3134 -0.9005
3.0000 3.0000 -7.0000 -0.0808 -1.0227 0.0365
5.0000 5.0000 -4.0000 -0.1757 -0.8339 0.5567
-5.0000 5.0000 -2.0000 0.9294 -0.2651 -0.1502
0.0000 -8.0000 -2.0000 -0.5665 0.1070 -0.7650
6.0000 -3.0000 2.0000 -0.8967 0.1474 0.3928
-6.0000 -0.0000 -2.0000 0.6802 -0.0221 -0.6311
-4.0000 7.0000 1.0000 0.9460 -0.0421 0.2864
-6.0000 -0.0000 4.0000 0.6481 0.6593 -0.2430
3.0000 -7.0000 -2.0000 -0.8291 -0.0373 -0.4347
-3.0000 5.0000 6.0000 0.6633 0.5751 0.5345
-0.0000 7.0000 -4.0000 0.5265 -0.7466 0.2975

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13860
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         76.495
_diffrn_reflns_theta_min         5.003
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -14.00   1.00    1.50    --  -40.71 -37.00 -60.00  103
  2  ω     14.00 117.00   1.00    1.50    --   40.71  37.00 -90.00  103
  3  ω    -33.00  70.00   1.00    1.50    --   40.71 -57.00 120.00  103
  4  ω     35.00  69.00   1.00    3.00    --  113.00 -30.00-150.00   34
  5  ω     35.00  69.00   1.00    3.00    --  113.00 -30.00-180.00   34
  6  ω     85.00 158.00   1.00    3.00    --  113.00  45.00 150.00   73
  7  ω     35.00  69.00   1.00    3.00    --  113.00 -30.00 -90.00   34
  8  ω     24.00 158.00   1.00    3.00    --  113.00   0.00 150.00  134
  9  ω     35.00  69.00   1.00    3.00    --  113.00 -30.00 -60.00   34
 10  ω     83.00 158.00   1.00    3.00    --  113.00  61.00 120.00   75
 11  ω     38.00  77.00   1.00    3.00    --  113.00 -45.00  90.00   39
 12  ω     34.00 147.00   1.00    3.00    --  113.00 -77.00 -30.00  113
 13  ω     83.00 158.00   1.00    3.00    --  113.00  61.00  30.00   75
 14  ω     38.00  77.00   1.00    3.00    --  113.00 -45.00 -60.00   39
 15  ω     39.00 143.00   1.00    3.00    --  113.00 -61.00  90.00  104
 16  ω     52.00 158.00   1.00    3.00    --  113.00  15.00  90.00  106
 17  ω     35.00  69.00   1.00    3.00    --  113.00 -30.00-120.00   34
 18  ω     35.00 150.00   1.00    3.00    --  113.00 178.00 -90.00  115
 19  ω     61.00 147.00   1.00    3.00    --  113.00 -77.00 105.85   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1115857000
_diffrn_orient_matrix_UB_12      0.0721514000
_diffrn_orient_matrix_UB_13      -0.0053634000
_diffrn_orient_matrix_UB_21      -0.0341743000
_diffrn_orient_matrix_UB_22      -0.0417634000
_diffrn_orient_matrix_UB_23      0.1135576000
_diffrn_orient_matrix_UB_31      0.0836258000
_diffrn_orient_matrix_UB_32      0.0794569000
_diffrn_orient_matrix_UB_33      0.0646841000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3333
_reflns_number_total             3557
_reflns_odcompleteness_completeness 98.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3557
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0495P)²+0.6855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0894
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C18(H18A,H18B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C3(H3), C9(H9), C7(H7), C11(H11), C10(H10)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.73333(3) 0.40573(2) 0.24236(2) 0.01734(10) Uani 1 1 d . . . . .
O2 O 0.81666(8) 0.32194(7) 0.24806(8) 0.0241(2) Uani 1 1 d . . . . .
O1 O 0.71834(9) 0.46743(7) 0.14282(7) 0.0245(2) Uani 1 1 d . . . . .
N1 N 0.59384(9) 0.36141(8) 0.25798(9) 0.0168(2) Uani 1 1 d . . . . .
N2 N 0.42160(10) 0.42485(8) 0.12843(9) 0.0202(2) Uani 1 1 d . . . . .
C13 C 0.58314(11) 0.27838(9) 0.34046(10) 0.0177(2) Uani 1 1 d . . . . .
H13 H 0.6658 0.2480 0.3565 0.021 Uiso 1 1 calc R . . . .
C4 C 0.75027(12) 0.58455(10) 0.35426(11) 0.0202(3) Uani 1 1 d . . . . .
H4 H 0.7131 0.6127 0.2871 0.024 Uiso 1 1 calc R . . . .
C5 C 0.77802(11) 0.48320(9) 0.36001(10) 0.0173(2) Uani 1 1 d . . . . .
C6 C 0.83452(11) 0.44071(10) 0.46035(11) 0.0208(3) Uani 1 1 d . . . . .
H6 H 0.8544 0.3731 0.4633 0.025 Uiso 1 1 calc R . . . .
C3 C 0.77882(12) 0.64328(10) 0.45047(11) 0.0219(3) Uani 1 1 d . . . . .
H3 H 0.7618 0.7114 0.4468 0.026 Uiso 1 1 calc R . . . .
C2 C 0.83235(12) 0.60192(10) 0.55220(11) 0.0216(3) Uani 1 1 d . . . . .
C14 C 0.49532(12) 0.19822(9) 0.28651(11) 0.0196(2) Uani 1 1 d . . . . .
H14A H 0.5232 0.1763 0.2156 0.024 Uiso 1 1 calc R . . . .
H14B H 0.4120 0.2256 0.2702 0.024 Uiso 1 1 calc R . . . .
C9 C 0.44695(12) 0.50260(10) 0.29610(11) 0.0218(3) Uani 1 1 d . . . . .
H9 H 0.4776 0.5212 0.3696 0.026 Uiso 1 1 calc R . . . .
C8 C 0.49280(11) 0.42798(9) 0.23275(10) 0.0180(2) Uani 1 1 d . . . . .
C18 C 0.54290(12) 0.31309(10) 0.45360(10) 0.0215(3) Uani 1 1 d . . . . .
H18A H 0.4611 0.3437 0.4407 0.026 Uiso 1 1 calc R . . . .
H18B H 0.6011 0.3629 0.4873 0.026 Uiso 1 1 calc R . . . .
C7 C 0.86062(12) 0.50028(10) 0.55531(11) 0.0226(3) Uani 1 1 d . . . . .
H7 H 0.8977 0.4720 0.6225 0.027 Uiso 1 1 calc R . . . .
C15 C 0.49291(13) 0.10927(10) 0.36740(12) 0.0237(3) Uani 1 1 d . . . . .
H15A H 0.4346 0.0595 0.3338 0.028 Uiso 1 1 calc R . . . .
H15B H 0.5750 0.0789 0.3788 0.028 Uiso 1 1 calc R . . . .
C11 C 0.33165(12) 0.49651(10) 0.12664(12) 0.0248(3) Uani 1 1 d . . . . .
H11 H 0.2714 0.5099 0.0661 0.030 Uiso 1 1 calc R . . . .
C12 C 0.44298(13) 0.36069(11) 0.03328(11) 0.0262(3) Uani 1 1 d . . . . .
H12A H 0.5266 0.3700 0.0151 0.039 Uiso 1 1 calc GR . . . .
H12B H 0.3851 0.3777 -0.0314 0.039 Uiso 1 1 calc GR . . . .
H12C H 0.4313 0.2921 0.0535 0.039 Uiso 1 1 calc GR . . . .
C10 C 0.34460(13) 0.54562(10) 0.22861(12) 0.0254(3) Uani 1 1 d . . . . .
H10 H 0.2951 0.5978 0.2496 0.030 Uiso 1 1 calc R . . . .
C16 C 0.45437(13) 0.14210(10) 0.48206(12) 0.0261(3) Uani 1 1 d . . . . .
H16A H 0.3689 0.1658 0.4717 0.031 Uiso 1 1 calc R . . . .
H16B H 0.4582 0.0852 0.5331 0.031 Uiso 1 1 calc R . . . .
C17 C 0.53890(13) 0.22471(11) 0.53495(11) 0.0267(3) Uani 1 1 d . . . . .
H17A H 0.6225 0.1986 0.5539 0.032 Uiso 1 1 calc R . . . .
H17B H 0.5086 0.2473 0.6046 0.032 Uiso 1 1 calc R . . . .
C1 C 0.85910(14) 0.66485(12) 0.65764(13) 0.0312(3) Uani 1 1 d . . . . .
H1A H 0.8481 0.7342 0.6381 0.047 Uiso 1 1 calc GR . . . .
H1B H 0.9434 0.6537 0.6905 0.047 Uiso 1 1 calc GR . . . .
H1C H 0.8028 0.6468 0.7114 0.047 Uiso 1 1 calc GR . . . .


_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 1.4344(10) . ?
S1 O1 1.4341(9) . ?
S1 N1 1.6485(10) . ?
S1 C5 1.7606(12) . ?
N1 C13 1.4931(15) . ?
N1 C8 1.4139(16) . ?
N2 C8 1.3807(16) . ?
N2 C11 1.3633(17) . ?
N2 C12 1.4565(17) . ?
C13 H13 0.9800 . ?
C13 C14 1.5235(17) . ?
C13 C18 1.5282(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.3889(18) . ?
C4 C3 1.3904(18) . ?
C5 C6 1.3947(17) . ?
C6 H6 0.9300 . ?
C6 C7 1.3820(18) . ?
C3 H3 0.9300 . ?
C3 C2 1.3915(19) . ?
C2 C7 1.3935(19) . ?
C2 C1 1.5075(18) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.5304(17) . ?
C9 H9 0.9300 . ?
C9 C8 1.3749(18) . ?
C9 C10 1.4113(19) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.5296(18) . ?
C7 H7 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.5302(19) . ?
C11 H11 0.9300 . ?
C11 C10 1.369(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C10 H10 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.523(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 N1 106.84(5) . . ?
O2 S1 C5 107.99(6) . . ?
O1 S1 O2 120.03(6) . . ?
O1 S1 N1 106.28(5) . . ?
O1 S1 C5 107.93(6) . . ?
N1 S1 C5 107.14(5) . . ?
C13 N1 S1 118.74(8) . . ?
C8 N1 S1 116.26(8) . . ?
C8 N1 C13 119.48(9) . . ?
C8 N2 C12 126.18(11) . . ?
C11 N2 C8 108.41(11) . . ?
C11 N2 C12 125.30(11) . . ?
N1 C13 H13 107.4 . . ?
N1 C13 C14 109.87(10) . . ?
N1 C13 C18 113.53(10) . . ?
C14 C13 H13 107.4 . . ?
C14 C13 C18 110.91(10) . . ?
C18 C13 H13 107.4 . . ?
C5 C4 H4 120.5 . . ?
C5 C4 C3 119.02(12) . . ?
C3 C4 H4 120.5 . . ?
C4 C5 S1 119.86(10) . . ?
C4 C5 C6 120.73(11) . . ?
C6 C5 S1 119.31(10) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.24(12) . . ?
C7 C6 H6 120.4 . . ?
C4 C3 H3 119.4 . . ?
C4 C3 C2 121.17(12) . . ?
C2 C3 H3 119.4 . . ?
C3 C2 C7 118.64(12) . . ?
C3 C2 C1 121.20(12) . . ?
C7 C2 C1 120.17(12) . . ?
C13 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
C13 C14 C15 109.79(10) . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C8 C9 H9 126.5 . . ?
C8 C9 C10 107.09(12) . . ?
C10 C9 H9 126.5 . . ?
N2 C8 N1 120.54(11) . . ?
C9 C8 N1 131.23(12) . . ?
C9 C8 N2 108.23(11) . . ?
C13 C18 H18A 109.6 . . ?
C13 C18 H18B 109.6 . . ?
C13 C18 C17 110.45(11) . . ?
H18A C18 H18B 108.1 . . ?
C17 C18 H18A 109.6 . . ?
C17 C18 H18B 109.6 . . ?
C6 C7 C2 121.17(12) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C14 111.03(11) . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
N2 C11 H11 125.6 . . ?
N2 C11 C10 108.83(11) . . ?
C10 C11 H11 125.6 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C10 H10 126.3 . . ?
C11 C10 C9 107.44(12) . . ?
C11 C10 H10 126.3 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 C15 111.31(11) . . ?
C17 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C16 C17 C18 111.12(11) . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
S1 N1 C13 C14 -134.28(9) . . . . ?
S1 N1 C13 C18 100.87(11) . . . . ?
S1 N1 C8 N2 98.07(12) . . . . ?
S1 N1 C8 C9 -81.36(15) . . . . ?
S1 C5 C6 C7 -174.94(9) . . . . ?
O2 S1 N1 C13 38.46(10) . . . . ?
O2 S1 N1 C8 -167.84(9) . . . . ?
O2 S1 C5 C4 154.18(10) . . . . ?
O2 S1 C5 C6 -29.58(11) . . . . ?
O1 S1 N1 C13 167.73(9) . . . . ?
O1 S1 N1 C8 -38.57(10) . . . . ?
O1 S1 C5 C4 23.03(12) . . . . ?
O1 S1 C5 C6 -160.73(10) . . . . ?
N1 S1 C5 C4 -91.06(11) . . . . ?
N1 S1 C5 C6 85.18(11) . . . . ?
N1 C13 C14 C15 175.30(10) . . . . ?
N1 C13 C18 C17 -177.83(10) . . . . ?
N2 C11 C10 C9 0.11(15) . . . . ?
C13 N1 C8 N2 -108.44(13) . . . . ?
C13 N1 C8 C9 72.14(17) . . . . ?
C13 C14 C15 C16 57.07(14) . . . . ?
C13 C18 C17 C16 -55.82(14) . . . . ?
C4 C5 C6 C7 1.27(18) . . . . ?
C4 C3 C2 C7 1.90(19) . . . . ?
C4 C3 C2 C1 -177.79(12) . . . . ?
C5 S1 N1 C13 -77.07(10) . . . . ?
C5 S1 N1 C8 76.63(10) . . . . ?
C5 C4 C3 C2 -1.15(19) . . . . ?
C5 C6 C7 C2 -0.49(19) . . . . ?
C3 C4 C5 S1 175.73(9) . . . . ?
C3 C4 C5 C6 -0.46(18) . . . . ?
C3 C2 C7 C6 -1.07(19) . . . . ?
C14 C13 C18 C17 57.89(14) . . . . ?
C14 C15 C16 C17 -55.77(15) . . . . ?
C8 N1 C13 C14 72.88(13) . . . . ?
C8 N1 C13 C18 -51.97(14) . . . . ?
C8 N2 C11 C10 0.10(15) . . . . ?
C8 C9 C10 C11 -0.28(15) . . . . ?
C18 C13 C14 C15 -58.36(13) . . . . ?
C15 C16 C17 C18 54.97(15) . . . . ?
C11 N2 C8 N1 -179.82(11) . . . . ?
C11 N2 C8 C9 -0.28(14) . . . . ?
C12 N2 C8 N1 -3.47(19) . . . . ?
C12 N2 C8 C9 176.08(12) . . . . ?
C12 N2 C11 C10 -176.30(12) . . . . ?
C10 C9 C8 N1 179.82(12) . . . . ?
C10 C9 C8 N2 0.34(14) . . . . ?
C1 C2 C7 C6 178.62(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-06-27
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with inert oil'
_olex2_submission_original_sample_id AM-1274(AM-III-026)
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.374
_oxdiff_exptl_absorpt_empirical_full_min 0.696
####################################################################### 
# 
# 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_p088
_database_code_depnum_ccdc_archive 'CCDC 1494734'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;
_audit_creation_date             2016-06-21
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 N2 O2 S'
_chemical_formula_sum            'C19 H20 N2 O2 S'
_chemical_formula_weight         340.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H20 N2 O2 S'
_chemical_oxdiff_usercomment     'Meyer_Koenig_AM-1272 (AM-III-024)'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.7933(3)
_cell_length_b                   8.92836(18)
_cell_length_c                   12.9799(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.209(3)
_cell_angle_gamma                90
_cell_volume                     1717.60(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7210
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      76.1310
_cell_measurement_theta_min      5.7670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.780
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.42b (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             720
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-9 1 -1 0.0641
4 -3 5 0.0791
9 0 2 0.0721
4 4 -6 0.0590
7 -3 1 0.0683
-10 -1 2 0.0751
9 3 -5 0.0555
-6 -1 -5 0.1290
-4 -1 8 0.0701
-8 -3 0 0.0747
-4 5 -3 0.0886
9 2 1 0.0990
2 6 -2 0.1131
9 -3 -3 0.0892
-3 4 6 0.1349
10 -1 -4 0.0662

_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.139
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-8.9977 0.9928 -0.9966 0.0834 0.1220 -0.9895
3.9997 -3.0000 4.9942 -0.5926 0.2748 0.7711
8.9964 0.0065 1.9997 0.0500 0.0350 1.0475
3.9971 4.0078 -5.9934 0.8844 -0.4746 -0.0368
7.0002 -2.9945 0.9917 -0.4350 -0.1927 0.8056
-9.9966 -1.0103 2.0000 -0.3466 0.3403 -0.8697
8.9961 3.0115 -4.9962 0.7520 -0.5208 0.5471
-5.9953 -1.0017 -5.0043 -0.0861 -0.4541 -0.9362
-4.0006 -1.0092 8.0022 -0.4542 0.8428 0.1433
-7.9946 -3.0071 -0.0065 -0.5887 -0.0115 -0.7829
-4.0023 4.9986 -2.9880 0.8592 0.0392 -0.6551
8.9949 2.0072 1.0043 0.4072 0.0409 0.9612
1.9945 6.0032 -1.9858 1.0662 0.0826 0.0113
9.0009 -2.9899 -3.0107 -0.2896 -0.6413 0.7386
-3.0049 3.9931 6.0139 0.4361 0.8900 0.0626
9.9991 -0.9883 -4.0062 0.0799 -0.6543 0.7537

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12915
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         76.324
_diffrn_reflns_theta_min         5.785
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -14.00   1.00    1.00    --  -40.71 -37.00 -60.00  103
  2  ω    -98.00  -2.00   1.00    1.00    --  -40.71 125.00  30.00   96
  3  ω      2.00  98.00   1.00    1.00    --   40.71-125.00  30.00   96
  4  ω    -35.00  67.00   1.00    1.00    --   40.71 -37.00  90.00  102
  5  ω     38.00  77.00   1.00    4.00    --  113.00 -45.00 120.00   39
  6  ω     29.00 109.00   1.00    4.00    --  113.00 -94.00  60.00   80
  7  ω     83.00 158.00   1.00    4.00    --  113.00  61.00  30.00   75
  8  ω     35.00 116.00   1.00    4.00    --  113.00-111.00 150.00   81
  9  ω     35.00 116.00   1.00    4.00    --  113.00-111.00  30.00   81
 10  ω     82.00 158.00   1.00    4.00    --  113.00  30.00-150.00   76
 11  ω     35.00 116.00   1.00    4.00    --  113.00-111.00 -90.00   81
 12  ω     39.00 131.00   1.00    4.00    --  113.00-142.00 170.00   92
 13  ω     35.00 116.00   1.00    4.00    --  113.00-111.00 -30.00   81
 14  ω     83.00 158.00   1.00    4.00    --  113.00  61.00  90.00   75
 15  ω     52.00 150.00   1.00    4.00    --  113.00 178.00 -60.00   98
 16  ω    108.00 134.00   1.00    4.00    --  113.00  61.00-120.00   26
 17  ω     46.00  81.00   1.00    4.00    --  113.00-111.00   0.00   35
 18  ω     84.00 115.00   1.00    4.00    --  113.00-111.00   0.00   31
 19  ω     85.00 152.00   1.00    4.00    --  113.00 111.00 -90.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0121180000
_diffrn_orient_matrix_UB_12      0.1636255000
_diffrn_orient_matrix_UB_13      -0.0300670000
_diffrn_orient_matrix_UB_21      -0.0189656000
_diffrn_orient_matrix_UB_22      0.0540128000
_diffrn_orient_matrix_UB_23      0.1026561000
_diffrn_orient_matrix_UB_31      0.1014538000
_diffrn_orient_matrix_UB_32      -0.0095248000
_diffrn_orient_matrix_UB_33      0.0674325000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3308
_reflns_number_total             3575
_reflns_odcompleteness_completeness 98.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+0.4807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0932
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C10(H10), C16(H16), C4(H4), C11(H11), C7(H7), C18(H18),
 C17(H17), C12(H12), C14(H14), C13(H13)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.21659(2) 0.50996(3) 0.25030(2) 0.02251(10) Uani 1 1 d . . . . .
O2 O 0.15833(6) 0.43572(12) 0.15443(7) 0.0303(2) Uani 1 1 d . . . . .
O1 O 0.27005(6) 0.63510(11) 0.23885(8) 0.0301(2) Uani 1 1 d . . . . .
N2 N 0.26031(7) 0.12021(12) 0.28143(9) 0.0261(2) Uani 1 1 d . . . . .
N1 N 0.28918(7) 0.38392(12) 0.32268(8) 0.0232(2) Uani 1 1 d . . . . .
C5 C 0.15162(8) 0.57054(14) 0.32907(10) 0.0217(2) Uani 1 1 d . . . . .
C15 C 0.25284(8) 0.24477(14) 0.33969(10) 0.0234(2) Uani 1 1 d . . . . .
C9 C 0.45191(8) 0.34120(15) 0.41342(10) 0.0246(3) Uani 1 1 d . . . . .
C6 C 0.05854(8) 0.55521(16) 0.28977(10) 0.0282(3) Uani 1 1 d . . . . .
H6 H 0.0294 0.5078 0.2231 0.034 Uiso 1 1 calc R . . . .
C3 C 0.14604(9) 0.69036(15) 0.49155(10) 0.0264(3) Uani 1 1 d . . . . .
H3 H 0.1757 0.7332 0.5599 0.032 Uiso 1 1 calc R . . . .
C10 C 0.48931(9) 0.35756(16) 0.33121(11) 0.0300(3) Uani 1 1 d . . . . .
H10 H 0.4651 0.4272 0.2755 0.036 Uiso 1 1 calc R . . . .
C16 C 0.21110(8) 0.20480(16) 0.41213(11) 0.0292(3) Uani 1 1 d . . . . .
H16 H 0.1976 0.2677 0.4615 0.035 Uiso 1 1 calc R . . . .
C8 C 0.37208(8) 0.43518(15) 0.41158(11) 0.0270(3) Uani 1 1 d . . . . .
H8A H 0.3634 0.4276 0.4818 0.032 Uiso 1 1 calc R . . . .
H8B H 0.3836 0.5394 0.3998 0.032 Uiso 1 1 calc R . . . .
C4 C 0.19560(8) 0.63886(15) 0.42945(10) 0.0254(3) Uani 1 1 d . . . . .
H4 H 0.2580 0.6499 0.4547 0.031 Uiso 1 1 calc R . . . .
C2 C 0.05200(9) 0.67891(16) 0.45314(11) 0.0276(3) Uani 1 1 d . . . . .
C11 C 0.56247(9) 0.27050(17) 0.33193(12) 0.0326(3) Uani 1 1 d . . . . .
H11 H 0.5867 0.2813 0.2764 0.039 Uiso 1 1 calc R . . . .
C7 C 0.00970(8) 0.61177(18) 0.35169(12) 0.0326(3) Uani 1 1 d . . . . .
H7 H -0.0529 0.6046 0.3246 0.039 Uiso 1 1 calc R . . . .
C18 C 0.22348(9) 0.00128(15) 0.31778(12) 0.0322(3) Uani 1 1 d . . . . .
H18 H 0.2202 -0.0966 0.2922 0.039 Uiso 1 1 calc R . . . .
C17 C 0.19235(9) 0.05041(17) 0.39788(12) 0.0335(3) Uani 1 1 d . . . . .
H17 H 0.1640 -0.0075 0.4360 0.040 Uiso 1 1 calc R . . . .
C12 C 0.59935(8) 0.16749(16) 0.41542(13) 0.0329(3) Uani 1 1 d . . . . .
H12 H 0.6482 0.1091 0.4159 0.039 Uiso 1 1 calc R . . . .
C14 C 0.48927(8) 0.23778(16) 0.49651(11) 0.0292(3) Uani 1 1 d . . . . .
H14 H 0.4648 0.2257 0.5516 0.035 Uiso 1 1 calc R . . . .
C13 C 0.56336(9) 0.15182(16) 0.49783(12) 0.0333(3) Uani 1 1 d . . . . .
H13 H 0.5886 0.0837 0.5544 0.040 Uiso 1 1 calc R . . . .
C19 C 0.30390(11) 0.11340(18) 0.19974(13) 0.0380(3) Uani 1 1 d . . . . .
H19A H 0.2958 0.2070 0.1612 0.057 Uiso 1 1 calc GR . . . .
H19B H 0.2776 0.0342 0.1487 0.057 Uiso 1 1 calc GR . . . .
H19C H 0.3672 0.0945 0.2353 0.057 Uiso 1 1 calc GR . . . .
C1 C -0.00081(10) 0.7402(2) 0.52040(12) 0.0396(3) Uani 1 1 d . . . . .
H1A H 0.0283 0.7125 0.5959 0.059 Uiso 1 1 calc GR . . . .
H1B H -0.0608 0.6997 0.4940 0.059 Uiso 1 1 calc GR . . . .
H1C H -0.0036 0.8473 0.5142 0.059 Uiso 1 1 calc GR . . . .


_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 1.4295(9) . ?
S1 O1 1.4389(10) . ?
S1 N1 1.6490(10) . ?
S1 C5 1.7649(12) . ?
N2 C15 1.3726(16) . ?
N2 C18 1.3703(18) . ?
N2 C19 1.4514(18) . ?
N1 C15 1.4175(16) . ?
N1 C8 1.4871(15) . ?
C5 C6 1.3864(17) . ?
C5 C4 1.3882(17) . ?
C15 C16 1.3691(19) . ?
C9 C10 1.3943(19) . ?
C9 C8 1.5078(17) . ?
C9 C14 1.3872(19) . ?
C6 H6 0.9300 . ?
C6 C7 1.3871(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.3819(18) . ?
C3 C2 1.3976(18) . ?
C10 H10 0.9300 . ?
C10 C11 1.3900(19) . ?
C16 H16 0.9300 . ?
C16 C17 1.409(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C4 H4 0.9300 . ?
C2 C7 1.390(2) . ?
C2 C1 1.5032(19) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(2) . ?
C7 H7 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.367(2) . ?
C17 H17 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.381(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.394(2) . ?
C13 H13 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.62(6) . . ?
O2 S1 N1 106.93(6) . . ?
O2 S1 C5 108.56(6) . . ?
O1 S1 N1 105.75(5) . . ?
O1 S1 C5 107.53(6) . . ?
N1 S1 C5 107.94(5) . . ?
C15 N2 C19 126.09(12) . . ?
C18 N2 C15 108.11(11) . . ?
C18 N2 C19 125.72(12) . . ?
C15 N1 S1 116.59(8) . . ?
C15 N1 C8 116.38(10) . . ?
C8 N1 S1 118.98(9) . . ?
C6 C5 S1 120.75(10) . . ?
C6 C5 C4 120.78(12) . . ?
C4 C5 S1 118.42(9) . . ?
N2 C15 N1 120.52(11) . . ?
C16 C15 N2 108.70(12) . . ?
C16 C15 N1 130.72(12) . . ?
C10 C9 C8 120.17(12) . . ?
C14 C9 C10 119.07(12) . . ?
C14 C9 C8 120.76(12) . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C7 118.82(12) . . ?
C7 C6 H6 120.6 . . ?
C4 C3 H3 119.5 . . ?
C4 C3 C2 120.92(12) . . ?
C2 C3 H3 119.5 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.48(13) . . ?
C11 C10 H10 119.8 . . ?
C15 C16 H16 126.4 . . ?
C15 C16 C17 107.10(13) . . ?
C17 C16 H16 126.4 . . ?
N1 C8 C9 110.38(10) . . ?
N1 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.55(11) . . ?
C3 C4 H4 120.2 . . ?
C3 C2 C1 120.04(12) . . ?
C7 C2 C3 118.24(12) . . ?
C7 C2 C1 121.71(12) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.99(13) . . ?
C12 C11 H11 120.0 . . ?
C6 C7 C2 121.63(12) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
N2 C18 H18 125.7 . . ?
C17 C18 N2 108.67(12) . . ?
C17 C18 H18 125.7 . . ?
C16 C17 H17 126.3 . . ?
C18 C17 C16 107.42(13) . . ?
C18 C17 H17 126.3 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.89(13) . . ?
C13 C12 H12 120.1 . . ?
C9 C14 H14 119.8 . . ?
C9 C14 C13 120.37(13) . . ?
C13 C14 H14 119.8 . . ?
C12 C13 C14 120.19(13) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
S1 N1 C15 N2 104.05(11) . . . . ?
S1 N1 C15 C16 -79.13(15) . . . . ?
S1 N1 C8 C9 -140.54(10) . . . . ?
S1 C5 C6 C7 -176.50(11) . . . . ?
S1 C5 C4 C3 178.54(10) . . . . ?
O2 S1 N1 C15 -47.80(10) . . . . ?
O2 S1 N1 C8 164.51(9) . . . . ?
O2 S1 C5 C6 -5.74(13) . . . . ?
O2 S1 C5 C4 176.59(10) . . . . ?
O1 S1 N1 C15 -176.31(9) . . . . ?
O1 S1 N1 C8 36.00(11) . . . . ?
O1 S1 C5 C6 125.02(11) . . . . ?
O1 S1 C5 C4 -52.66(11) . . . . ?
N2 C15 C16 C17 0.03(14) . . . . ?
N2 C18 C17 C16 -0.40(15) . . . . ?
N1 S1 C5 C6 -121.31(11) . . . . ?
N1 S1 C5 C4 61.02(11) . . . . ?
N1 C15 C16 C17 -177.08(12) . . . . ?
C5 S1 N1 C15 68.84(10) . . . . ?
C5 S1 N1 C8 -78.85(10) . . . . ?
C5 C6 C7 C2 -2.0(2) . . . . ?
C15 N2 C18 C17 0.43(14) . . . . ?
C15 N1 C8 C9 71.71(14) . . . . ?
C15 C16 C17 C18 0.23(15) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C9 C14 C13 C12 -0.9(2) . . . . ?
C6 C5 C4 C3 0.9(2) . . . . ?
C3 C2 C7 C6 0.9(2) . . . . ?
C10 C9 C8 N1 72.45(15) . . . . ?
C10 C9 C14 C13 0.2(2) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C8 N1 C15 N2 -107.42(13) . . . . ?
C8 N1 C15 C16 69.41(16) . . . . ?
C8 C9 C10 C11 -179.51(12) . . . . ?
C8 C9 C14 C13 -179.71(12) . . . . ?
C4 C5 C6 C7 1.1(2) . . . . ?
C4 C3 C2 C7 1.2(2) . . . . ?
C4 C3 C2 C1 -178.02(13) . . . . ?
C2 C3 C4 C5 -2.0(2) . . . . ?
C11 C12 C13 C14 0.9(2) . . . . ?
C18 N2 C15 N1 177.18(10) . . . . ?
C18 N2 C15 C16 -0.28(14) . . . . ?
C14 C9 C10 C11 0.6(2) . . . . ?
C14 C9 C8 N1 -107.65(14) . . . . ?
C19 N2 C15 N1 0.22(18) . . . . ?
C19 N2 C15 C16 -177.24(12) . . . . ?
C19 N2 C18 C17 177.40(13) . . . . ?
C1 C2 C7 C6 -179.95(14) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-06-20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.238
_oxdiff_exptl_absorpt_empirical_full_min 0.711
####################################################################### 
# 
# 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_p089
_database_code_depnum_ccdc_archive 'CCDC 1494735'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;
_audit_creation_date             2016-07-21
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C15 H20 N2 O2 S)'
_chemical_formula_sum            'C30 H40 N4 O4 S2'
_chemical_formula_weight         584.78
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H20 N2 O2 S'
_chemical_oxdiff_usercomment     'Meyer_Koenig_AM-1273 (AM-III-025)'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   18.0343(3)
_cell_length_b                   7.58100(10)
_cell_length_c                   23.5816(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.174(2)
_cell_angle_gamma                90
_cell_volume                     3045.18(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    23477
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.4040
_cell_measurement_theta_min      3.6700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.914
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.42b (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1248
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
10 2 -8 0.0264
9 3 -5 0.0242
2 3 11 0.0521
5 4 -2 0.0514
1 -2 -13 0.0493
11 2 -4 0.0221
-11 -1 3 0.0518
-4 -4 9 0.0728
11 1 1 0.0213
-7 -2 12 0.0638
8 -2 -11 0.0545
-10 1 12 0.0403
9 2 -11 0.0282
10 -3 -3 0.0460
-12 1 6 0.0648
5 2 -14 0.0332

_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.08
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
9.9982 1.9982 -7.9823 0.1089 0.5460 0.8059
8.9995 2.9970 -4.9837 0.2978 0.3457 0.8716
1.9980 2.9944 10.9984 0.9557 -0.2771 0.2863
5.0035 3.9966 -1.9878 0.3298 -0.0596 0.8544
1.0020 -1.9953 -12.9927 -0.8778 0.3953 0.0124
10.9953 1.9968 -3.9843 0.4171 0.5783 0.7356
-10.9930 -0.9971 2.9867 -0.4320 -0.6741 -0.5443
-4.0080 -3.9989 8.9835 0.1703 0.0649 -0.9982
10.9910 0.9960 1.0104 0.6879 0.6381 0.4464
-7.0031 -2.0002 11.9819 0.3038 -0.3770 -0.8210
7.9944 -1.9978 -10.9881 -0.3841 0.8558 0.1569
-9.9949 0.9988 11.9841 0.2944 -0.8967 -0.4035
9.0007 1.9993 -10.9809 -0.1353 0.5047 0.8518
9.9867 -3.0001 -2.9939 0.1832 1.0252 -0.1505
-11.9900 1.0010 5.9868 -0.1940 -0.9793 -0.3118
5.0059 2.0013 -13.9822 -0.5363 0.2583 0.8147

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            45303
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         73.550
_diffrn_reflns_theta_min         3.749
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -14.00   1.00    3.50    --  -40.71 -37.00-120.00  103
  2  ω    -98.00  -2.00   1.00    3.50    --  -40.71 125.00-150.00   96
  3  ω   -115.00 -11.00   1.00    3.50    --  -40.71 -57.00-180.00  104
  4  ω    -34.00  68.00   1.00    3.50    --   40.71 -46.00  40.00  102
  5  ω     32.00  77.00   1.00   14.00    --  106.98 -45.00-180.00   45
  6  ω     73.00 158.00   1.00   14.00    --  106.98 125.00  30.00   85
  7  ω     46.00 158.00   1.00   14.00    --  106.98  15.00-120.00  112
  8  ω     32.00  77.00   1.00   14.00    --  106.98 -45.00   0.00   45
  9  ω     77.00 158.00   1.00   14.00    --  106.98  61.00  90.00   81
 10  ω     73.00 158.00   1.00   14.00    --  106.98  77.00-120.00   85
 11  ω     32.00  77.00   1.00   14.00    --  106.98 -45.00 -90.00   45
 12  ω     77.00 158.00   1.00   14.00    --  106.98  61.00 120.00   81
 13  ω     29.00  69.00   1.00   14.00    --  106.98 -30.00 -60.00   40
 14  ω     29.00  69.00   1.00   14.00    --  106.98 -30.00 -30.00   40
 15  ω     77.00 158.00   1.00   14.00    --  106.98  61.00 -30.00   81
 16  ω     73.00 158.00   1.00   14.00    --  106.98  77.00 -90.00   85
 17  ω     77.00 158.00   1.00   14.00    --  106.98  61.00-120.00   81
 18  ω     75.00 158.00   1.00   14.00    --  106.98  68.00 -59.96   83
 19  ω    -98.00  -2.00   1.00    3.50    --  -40.71 125.00 120.00   96
 20  ω   -119.00  -7.00   1.00    3.50    --  -40.71 -77.00  60.00  112
 21  ω   -119.00  -7.00   1.00    3.50    --  -40.71 -77.00 150.00  112
 22  ω      2.00  98.00   1.00    3.50    --   40.71-125.00  30.00   96
 23  ω      7.00 119.00   1.00    3.50    --   40.71  77.00  60.00  112
 24  ω      7.00 119.00   1.00    3.50    --   40.71  77.00 -30.00  112
 25  ω     32.00 121.00   1.00   14.00    --  106.98-125.00-120.00   89
 26  ω     73.00 158.00   1.00   14.00    --  106.98  77.00-180.00   85
 27  ω     32.00  77.00   1.00   14.00    --  106.98 -45.00  90.00   45
 28  ω     23.00 109.00   1.00   14.00    --  106.98 -94.00 -60.00   86
 29  ω     77.00 158.00   1.00   14.00    --  106.98  61.00  60.00   81
 30  ω     28.00 141.00   1.00   14.00    --  106.98 -77.00   0.00  113
 31  ω     23.00 109.00   1.00   14.00    --  106.98 -94.00  90.00   86
 32  ω     77.00 102.00   1.00   14.00    --  106.98  61.00 150.00   25
 33  ω     79.00 158.00   1.00   14.00    --  106.98  45.00  30.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0522636000
_diffrn_orient_matrix_UB_12      0.0489643000
_diffrn_orient_matrix_UB_13      0.0640734000
_diffrn_orient_matrix_UB_21      0.0684020000
_diffrn_orient_matrix_UB_22      -0.1050398000
_diffrn_orient_matrix_UB_23      -0.0090197000
_diffrn_orient_matrix_UB_31      0.0277355000
_diffrn_orient_matrix_UB_32      0.1668986000
_diffrn_orient_matrix_UB_33      -0.0244476000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5586
_reflns_number_total             6102
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         6102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0547P)²+1.6355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1086
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C29(H29)
2.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C2(H2), C6(H6), C3(H3), C26(H26), C23(H23), C38(H38), C16(H16),
 C25(H25), C5(H5), C17(H17), C18(H18), C37(H37), C36(H36)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C30(H30A,H30B,H30C), C20(H20A,H20B,H20C), C34(H34A,H34B,
 H34C), C14(H14A,H14B,H14C), C40(H40A,H40B,H40C), C31(H31A,H31B,H31C), C11(H11A,
 H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
S7 S 0.21816(2) 0.49535(5) 0.36703(2) 0.02443(11) Uani 1 1 d . . . . .
S27 S 0.28897(2) 0.60886(5) 0.64215(2) 0.02267(11) Uani 1 1 d . . . . .
O33 O 0.29844(7) 0.43770(15) 0.61963(5) 0.0287(2) Uani 1 1 d . . . . .
O32 O 0.21302(6) 0.69028(16) 0.62404(5) 0.0294(3) Uani 1 1 d . . . . .
O13 O 0.29417(6) 0.57636(18) 0.38446(5) 0.0326(3) Uani 1 1 d . . . . .
O12 O 0.20876(7) 0.32223(16) 0.38826(5) 0.0317(3) Uani 1 1 d . . . . .
N28 N 0.34718(7) 0.74205(18) 0.62125(6) 0.0238(3) Uani 1 1 d . . . . .
N8 N 0.16146(7) 0.62648(18) 0.39034(6) 0.0242(3) Uani 1 1 d . . . . .
N19 N 0.08257(8) 0.47472(19) 0.44032(6) 0.0289(3) Uani 1 1 d . . . . .
N35 N 0.43473(8) 0.5886(2) 0.57943(6) 0.0323(3) Uani 1 1 d . . . . .
C39 C 0.42260(9) 0.6749(2) 0.62679(7) 0.0250(3) Uani 1 1 d . . . . .
C22 C 0.38599(9) 0.4834(2) 0.74960(7) 0.0252(3) Uani 1 1 d . . . . .
H22 H 0.4103 0.4191 0.7271 0.030 Uiso 1 1 calc R . . . .
C1 C 0.18314(9) 0.4878(2) 0.28772(7) 0.0238(3) Uani 1 1 d . . . . .
C15 C 0.08835(9) 0.5572(2) 0.38999(7) 0.0247(3) Uani 1 1 d . . . . .
C21 C 0.32278(9) 0.5933(2) 0.72126(7) 0.0234(3) Uani 1 1 d . . . . .
C2 C 0.11901(9) 0.3824(2) 0.25800(7) 0.0259(3) Uani 1 1 d . . . . .
H2 H 0.0941 0.3161 0.2796 0.031 Uiso 1 1 calc R . . . .
C6 C 0.22138(9) 0.5852(2) 0.25569(7) 0.0279(3) Uani 1 1 d . . . . .
H6 H 0.2647 0.6541 0.2757 0.034 Uiso 1 1 calc R . . . .
C4 C 0.12928(10) 0.4761(2) 0.16274(7) 0.0292(3) Uani 1 1 d . . . . .
C3 C 0.09270(9) 0.3772(2) 0.19574(7) 0.0284(3) Uani 1 1 d . . . . .
H3 H 0.0499 0.3066 0.1757 0.034 Uiso 1 1 calc R . . . .
C24 C 0.37629(10) 0.5672(2) 0.84584(7) 0.0291(3) Uani 1 1 d . . . . .
C26 C 0.28587(9) 0.6892(2) 0.75447(7) 0.0280(3) Uani 1 1 d . . . . .
H26 H 0.2434 0.7617 0.7353 0.034 Uiso 1 1 calc R . . . .
C23 C 0.41219(9) 0.4708(2) 0.81159(7) 0.0271(3) Uani 1 1 d . . . . .
H23 H 0.4542 0.3972 0.8307 0.032 Uiso 1 1 calc R . . . .
C9 C 0.17266(9) 0.8214(2) 0.39034(8) 0.0296(3) Uani 1 1 d . . . . .
H9 H 0.2283 0.8439 0.3966 0.036 Uiso 1 1 calc R . . . .
C29 C 0.33513(9) 0.9370(2) 0.62196(8) 0.0302(4) Uani 1 1 d . . . . .
H29 H 0.2789 0.9582 0.6135 0.036 Uiso 1 1 calc R . . . .
C38 C 0.49216(9) 0.6769(2) 0.67389(8) 0.0293(3) Uani 1 1 d . . . . .
H38 H 0.5006 0.7269 0.7115 0.035 Uiso 1 1 calc R . . . .
C16 C 0.01548(9) 0.5581(2) 0.34691(8) 0.0297(3) Uani 1 1 d . . . . .
H16 H 0.0027 0.6058 0.3086 0.036 Uiso 1 1 calc R . . . .
C25 C 0.31303(10) 0.6755(2) 0.81646(8) 0.0304(4) Uani 1 1 d . . . . .
H25 H 0.2886 0.7399 0.8389 0.037 Uiso 1 1 calc R . . . .
C5 C 0.19409(10) 0.5783(2) 0.19357(7) 0.0303(4) Uani 1 1 d . . . . .
H5 H 0.2196 0.6432 0.1720 0.036 Uiso 1 1 calc R . . . .
C10 C 0.12513(11) 0.9078(2) 0.33154(9) 0.0372(4) Uani 1 1 d . . . . .
H10A H 0.1381 0.8543 0.2991 0.056 Uiso 1 1 calc GR . . . .
H10B H 0.1371 1.0314 0.3331 0.056 Uiso 1 1 calc GR . . . .
H10C H 0.0702 0.8922 0.3252 0.056 Uiso 1 1 calc GR . . . .
C17 C -0.03652(10) 0.4733(2) 0.37164(9) 0.0348(4) Uani 1 1 d . . . . .
H17 H -0.0900 0.4551 0.3527 0.042 Uiso 1 1 calc R . . . .
C18 C 0.00649(10) 0.4230(2) 0.42856(8) 0.0345(4) Uani 1 1 d . . . . .
H18 H -0.0130 0.3630 0.4551 0.041 Uiso 1 1 calc R . . . .
C37 C 0.54831(10) 0.5888(2) 0.65441(9) 0.0365(4) Uani 1 1 d . . . . .
H37 H 0.6007 0.5699 0.6768 0.044 Uiso 1 1 calc R . . . .
C30 C 0.37857(11) 1.0210(2) 0.68217(9) 0.0376(4) Uani 1 1 d . . . . .
H30A H 0.3625 0.9659 0.7129 0.056 Uiso 1 1 calc GR . . . .
H30B H 0.3666 1.1446 0.6806 0.056 Uiso 1 1 calc GR . . . .
H30C H 0.4341 1.0055 0.6910 0.056 Uiso 1 1 calc GR . . . .
C20 C 0.14646(11) 0.4421(3) 0.49579(8) 0.0359(4) Uani 1 1 d . . . . .
H20A H 0.1746 0.3383 0.4914 0.054 Uiso 1 1 calc GR . . . .
H20B H 0.1256 0.4251 0.5280 0.054 Uiso 1 1 calc GR . . . .
H20C H 0.1815 0.5414 0.5047 0.054 Uiso 1 1 calc GR . . . .
C36 C 0.51144(11) 0.5363(3) 0.59673(9) 0.0397(4) Uani 1 1 d . . . . .
H36 H 0.5348 0.4748 0.5729 0.048 Uiso 1 1 calc R . . . .
C34 C 0.40627(12) 0.5548(3) 0.91321(8) 0.0402(4) Uani 1 1 d . . . . .
H34A H 0.4324 0.4439 0.9250 0.060 Uiso 1 1 calc GR . . . .
H34B H 0.3630 0.5634 0.9283 0.060 Uiso 1 1 calc GR . . . .
H34C H 0.4425 0.6493 0.9293 0.060 Uiso 1 1 calc GR . . . .
C14 C 0.09886(12) 0.4755(3) 0.09515(8) 0.0408(4) Uani 1 1 d . . . . .
H14A H 0.0767 0.3620 0.0811 0.061 Uiso 1 1 calc GR . . . .
H14B H 0.1413 0.4994 0.0801 0.061 Uiso 1 1 calc GR . . . .
H14C H 0.0592 0.5646 0.0811 0.061 Uiso 1 1 calc GR . . . .
C40 C 0.37627(12) 0.5573(3) 0.52088(8) 0.0453(5) Uani 1 1 d . . . . .
H40A H 0.3279 0.5204 0.5260 0.068 Uiso 1 1 calc GR . . . .
H40B H 0.3946 0.4667 0.5003 0.068 Uiso 1 1 calc GR . . . .
H40C H 0.3677 0.6640 0.4977 0.068 Uiso 1 1 calc GR . . . .
C31 C 0.35837(12) 1.0203(3) 0.57156(10) 0.0451(5) Uani 1 1 d . . . . .
H31A H 0.4136 1.0034 0.5792 0.068 Uiso 1 1 calc GR . . . .
H31B H 0.3469 1.1442 0.5696 0.068 Uiso 1 1 calc GR . . . .
H31C H 0.3293 0.9657 0.5341 0.068 Uiso 1 1 calc GR . . . .
C11 C 0.15345(13) 0.9004(3) 0.44310(9) 0.0442(5) Uani 1 1 d . . . . .
H11A H 0.0993 0.8786 0.4384 0.066 Uiso 1 1 calc GR . . . .
H11B H 0.1627 1.0253 0.4445 0.066 Uiso 1 1 calc GR . . . .
H11C H 0.1862 0.8473 0.4797 0.066 Uiso 1 1 calc GR . . . .


_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
S7 O13 1.4335(12) . ?
S7 O12 1.4345(12) . ?
S7 N8 1.6448(13) . ?
S7 C1 1.7675(16) . ?
S27 O33 1.4334(12) . ?
S27 O32 1.4336(11) . ?
S27 N28 1.6445(13) . ?
S27 C21 1.7658(16) . ?
N28 C39 1.4177(19) . ?
N28 C29 1.495(2) . ?
N8 C15 1.4167(19) . ?
N8 C9 1.491(2) . ?
N19 C15 1.375(2) . ?
N19 C18 1.365(2) . ?
N19 C20 1.453(2) . ?
N35 C39 1.373(2) . ?
N35 C36 1.366(2) . ?
N35 C40 1.455(2) . ?
C39 C38 1.376(2) . ?
C22 H22 0.9300 . ?
C22 C21 1.393(2) . ?
C22 C23 1.384(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.391(2) . ?
C15 C16 1.372(2) . ?
C21 C26 1.388(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.385(2) . ?
C4 C3 1.393(2) . ?
C4 C5 1.392(2) . ?
C4 C14 1.506(2) . ?
C3 H3 0.9300 . ?
C24 C23 1.396(2) . ?
C24 C25 1.392(2) . ?
C24 C34 1.504(2) . ?
C26 H26 0.9300 . ?
C26 C25 1.385(2) . ?
C23 H23 0.9300 . ?
C9 H9 0.9800 . ?
C9 C10 1.518(2) . ?
C9 C11 1.520(2) . ?
C29 H29 0.9800 . ?
C29 C30 1.518(3) . ?
C29 C31 1.521(3) . ?
C38 H38 0.9300 . ?
C38 C37 1.410(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.411(2) . ?
C25 H25 0.9300 . ?
C5 H5 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C17 H17 0.9300 . ?
C17 C18 1.366(3) . ?
C18 H18 0.9300 . ?
C37 H37 0.9300 . ?
C37 C36 1.362(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C36 H36 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O13 S7 O12 120.22(8) . . ?
O13 S7 N8 106.63(7) . . ?
O13 S7 C1 107.04(7) . . ?
O12 S7 N8 106.17(7) . . ?
O12 S7 C1 107.31(7) . . ?
N8 S7 C1 109.15(7) . . ?
O33 S27 O32 119.86(7) . . ?
O33 S27 N28 106.21(7) . . ?
O33 S27 C21 106.81(7) . . ?
O32 S27 N28 106.73(7) . . ?
O32 S27 C21 107.95(7) . . ?
N28 S27 C21 108.94(7) . . ?
C39 N28 S27 116.08(11) . . ?
C39 N28 C29 119.51(12) . . ?
C29 N28 S27 119.62(10) . . ?
C15 N8 S7 116.97(11) . . ?
C15 N8 C9 119.55(13) . . ?
C9 N8 S7 119.98(11) . . ?
C15 N19 C20 126.30(14) . . ?
C18 N19 C15 108.14(14) . . ?
C18 N19 C20 125.53(15) . . ?
C39 N35 C40 126.18(15) . . ?
C36 N35 C39 108.16(15) . . ?
C36 N35 C40 125.66(16) . . ?
N35 C39 N28 120.05(14) . . ?
N35 C39 C38 108.38(14) . . ?
C38 C39 N28 131.57(15) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C23 C22 C21 119.34(14) . . ?
C2 C1 S7 120.06(12) . . ?
C6 C1 S7 119.27(12) . . ?
C6 C1 C2 120.67(15) . . ?
N19 C15 N8 119.85(14) . . ?
C16 C15 N8 131.73(15) . . ?
C16 C15 N19 108.40(14) . . ?
C22 C21 S27 119.42(12) . . ?
C26 C21 S27 119.86(12) . . ?
C26 C21 C22 120.72(15) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.22(15) . . ?
C3 C2 H2 120.4 . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.15(15) . . ?
C5 C6 H6 120.4 . . ?
C3 C4 C14 120.99(16) . . ?
C5 C4 C3 118.58(15) . . ?
C5 C4 C14 120.42(16) . . ?
C2 C3 C4 121.06(15) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C23 C24 C34 120.31(16) . . ?
C25 C24 C23 118.75(15) . . ?
C25 C24 C34 120.94(15) . . ?
C21 C26 H26 120.4 . . ?
C25 C26 C21 119.19(15) . . ?
C25 C26 H26 120.4 . . ?
C22 C23 C24 120.84(15) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
N8 C9 H9 107.8 . . ?
N8 C9 C10 113.05(14) . . ?
N8 C9 C11 108.87(14) . . ?
C10 C9 H9 107.8 . . ?
C10 C9 C11 111.42(16) . . ?
C11 C9 H9 107.8 . . ?
N28 C29 H29 107.7 . . ?
N28 C29 C30 113.13(14) . . ?
N28 C29 C31 108.85(15) . . ?
C30 C29 H29 107.7 . . ?
C30 C29 C31 111.52(16) . . ?
C31 C29 H29 107.7 . . ?
C39 C38 H38 126.5 . . ?
C39 C38 C37 107.09(16) . . ?
C37 C38 H38 126.5 . . ?
C15 C16 H16 126.4 . . ?
C15 C16 C17 107.25(16) . . ?
C17 C16 H16 126.4 . . ?
C24 C25 H25 119.4 . . ?
C26 C25 C24 121.16(15) . . ?
C26 C25 H25 119.4 . . ?
C6 C5 C4 121.30(15) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C17 H17 126.5 . . ?
C18 C17 C16 107.07(15) . . ?
C18 C17 H17 126.5 . . ?
N19 C18 C17 109.14(15) . . ?
N19 C18 H18 125.4 . . ?
C17 C18 H18 125.4 . . ?
C38 C37 H37 126.4 . . ?
C36 C37 C38 107.23(15) . . ?
C36 C37 H37 126.4 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N19 C20 H20A 109.5 . . ?
N19 C20 H20B 109.5 . . ?
N19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N35 C36 H36 125.4 . . ?
C37 C36 N35 109.13(16) . . ?
C37 C36 H36 125.4 . . ?
C24 C34 H34A 109.5 . . ?
C24 C34 H34B 109.5 . . ?
C24 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N35 C40 H40A 109.5 . . ?
N35 C40 H40B 109.5 . . ?
N35 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
S7 N8 C15 N19 91.45(16) . . . . ?
S7 N8 C15 C16 -90.3(2) . . . . ?
S7 N8 C9 C10 89.02(16) . . . . ?
S7 N8 C9 C11 -146.59(13) . . . . ?
S7 C1 C2 C3 -179.57(12) . . . . ?
S7 C1 C6 C5 179.66(12) . . . . ?
S27 N28 C39 N35 91.40(16) . . . . ?
S27 N28 C39 C38 -87.9(2) . . . . ?
S27 N28 C29 C30 87.64(15) . . . . ?
S27 N28 C29 C31 -147.79(13) . . . . ?
S27 C21 C26 C25 179.96(12) . . . . ?
O33 S27 N28 C39 -41.98(13) . . . . ?
O33 S27 N28 C29 162.64(12) . . . . ?
O33 S27 C21 C22 34.86(14) . . . . ?
O33 S27 C21 C26 -144.58(13) . . . . ?
O32 S27 N28 C39 -170.94(11) . . . . ?
O32 S27 N28 C29 33.67(14) . . . . ?
O32 S27 C21 C22 165.00(12) . . . . ?
O32 S27 C21 C26 -14.45(15) . . . . ?
O13 S7 N8 C15 -166.72(11) . . . . ?
O13 S7 N8 C9 34.47(14) . . . . ?
O13 S7 C1 C2 165.81(13) . . . . ?
O13 S7 C1 C6 -12.85(15) . . . . ?
O12 S7 N8 C15 -37.40(13) . . . . ?
O12 S7 N8 C9 163.79(12) . . . . ?
O12 S7 C1 C2 35.50(14) . . . . ?
O12 S7 C1 C6 -143.17(13) . . . . ?
N28 S27 C21 C22 -79.47(13) . . . . ?
N28 S27 C21 C26 101.09(13) . . . . ?
N28 C39 C38 C37 179.38(16) . . . . ?
N8 S7 C1 C2 -79.15(14) . . . . ?
N8 S7 C1 C6 102.19(13) . . . . ?
N8 C15 C16 C17 -178.50(16) . . . . ?
N19 C15 C16 C17 -0.08(19) . . . . ?
N35 C39 C38 C37 -0.01(19) . . . . ?
C39 N28 C29 C30 -66.90(19) . . . . ?
C39 N28 C29 C31 57.67(19) . . . . ?
C39 N35 C36 C37 -0.2(2) . . . . ?
C39 C38 C37 C36 -0.1(2) . . . . ?
C22 C21 C26 C25 0.5(2) . . . . ?
C1 S7 N8 C15 77.97(13) . . . . ?
C1 S7 N8 C9 -80.83(13) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C1 C6 C5 C4 0.0(3) . . . . ?
C15 N8 C9 C10 -69.24(19) . . . . ?
C15 N8 C9 C11 55.1(2) . . . . ?
C15 N19 C18 C17 -0.7(2) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C21 S27 N28 C39 72.74(13) . . . . ?
C21 S27 N28 C29 -82.64(13) . . . . ?
C21 C22 C23 C24 -0.2(2) . . . . ?
C21 C26 C25 C24 -0.3(2) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C23 C22 C21 S27 -179.72(12) . . . . ?
C23 C22 C21 C26 -0.3(2) . . . . ?
C23 C24 C25 C26 -0.3(2) . . . . ?
C9 N8 C15 N19 -109.65(17) . . . . ?
C9 N8 C15 C16 68.6(2) . . . . ?
C29 N28 C39 N35 -113.19(17) . . . . ?
C29 N28 C39 C38 67.5(2) . . . . ?
C38 C37 C36 N35 0.2(2) . . . . ?
C16 C17 C18 N19 0.7(2) . . . . ?
C25 C24 C23 C22 0.5(2) . . . . ?
C5 C4 C3 C2 1.2(2) . . . . ?
C18 N19 C15 N8 179.13(14) . . . . ?
C18 N19 C15 C16 0.49(19) . . . . ?
C20 N19 C15 N8 -2.9(2) . . . . ?
C20 N19 C15 C16 178.50(16) . . . . ?
C20 N19 C18 C17 -178.76(16) . . . . ?
C36 N35 C39 N28 -179.36(15) . . . . ?
C36 N35 C39 C38 0.10(19) . . . . ?
C34 C24 C23 C22 -178.88(16) . . . . ?
C34 C24 C25 C26 179.12(16) . . . . ?
C14 C4 C3 C2 -177.77(15) . . . . ?
C14 C4 C5 C6 177.85(16) . . . . ?
C40 N35 C39 N28 0.5(3) . . . . ?
C40 N35 C39 C38 179.98(17) . . . . ?
C40 N35 C36 C37 179.96(18) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-07-19
_olex2_date_sample_submission    2016-06-15
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a Lindemann tube with inert oil'
_olex2_submission_original_sample_id AM-1273(AM-III-025)
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.395
_oxdiff_exptl_absorpt_empirical_full_min 0.701
####################################################################### 
# 
# 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_mp_nc
_database_code_depnum_ccdc_archive 'CCDC 1494736'
_audit_update_record             
;
2016-07-21 deposited with the CCDC.
2016-08-12 downloaded from the CCDC.
;
_audit_creation_date             2016-06-29
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H16 N2 O2 S2'
_chemical_formula_sum            'C12 H16 N2 O2 S2'
_chemical_formula_weight         284.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H16 N2 O2 S2'
_chemical_oxdiff_usercomment     'Meyer_Koenig_AM-1269 (AM-III-021),F.3-5'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.6626(5)
_cell_length_b                   5.39440(16)
_cell_length_c                   18.2386(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.435(4)
_cell_angle_gamma                90
_cell_volume                     1323.60(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6561
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.1540
_cell_measurement_theta_min      4.9490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.621
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.42b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-9 0 1 0.0469
2 0 -12 0.0283
-6 0 11 0.0148
6 0 -11 0.0216
-5 -3 2 0.1651
-1 3 -2 0.2088
9 0 -1 0.0155

_exptl_crystal_size_max          0.431
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.036
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-9.0120 -0.0039 1.0222 -0.1916 -0.7752 0.6005
1.9843 -0.0051 -11.9962 -0.9853 0.2425 0.2046
-5.9919 0.0027 11.0071 0.7741 -0.5784 0.1037
5.9919 -0.0027 -11.0071 -0.7741 0.5784 -0.1037
-5.0006 -2.9990 2.0168 -0.2350 -0.8998 -0.3823
-1.0084 2.9961 -2.0015 0.0491 0.3870 0.8018
9.0120 0.0039 -1.0222 0.1916 0.7752 -0.6005

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12291
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         73.425
_diffrn_reflns_theta_min         4.992
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  33.00   1.00    2.00    --  -40.71  57.00  30.00  103
  2  ω     14.00 117.00   1.00    2.00    --   40.71  37.00   0.00  103
  3  ω     14.00 117.00   1.00    2.00    --   40.71  37.00  90.00  103
  4  ω      2.00  98.00   1.00    2.00    --   40.71-125.00 -90.00   96
  5  ω     23.00 109.00   1.00    8.00    --  106.98 -94.00  30.00   86
  6  ω     77.00 158.00   1.00    8.00    --  106.98  61.00 -90.00   81
  7  ω     79.00 158.00   1.00    8.00    --  106.98  50.00 -45.00   79
  8  ω     29.00  69.00   1.00    8.00    --  106.98 -30.00  90.00   40
  9  ω     23.00 109.00   1.00    8.00    --  106.98 -94.00-150.00   86
 10  ω     73.00 158.00   1.00    8.00    --  106.98  77.00  30.00   85
 11  ω     77.00 158.00   1.00    8.00    --  106.98  61.00   0.00   81
 12  ω     73.00 158.00   1.00    8.00    --  106.98  77.00  60.00   85
 13  ω     23.00 109.00   1.00    8.00    --  106.98 -94.00-120.00   86
 14  ω     77.00 158.00   1.00    8.00    --  106.98  61.00  30.00   81
 15  ω     77.00 158.00   1.00    8.00    --  106.98  61.00  90.00   81
 16  ω     32.00 121.00   1.00    8.00    --  106.98-125.00-150.00   89
 17  ω     29.00  69.00   1.00    8.00    --  106.98 -30.00  30.00   40
 18  ω    -67.00  35.00   1.00    2.00    --  -40.71  37.00 150.00  102
 19  ω     11.00 115.00   1.00    2.00    --   40.71  57.00 150.00  104
 20  ω      7.00  71.00   1.00    2.00    --   40.71  77.00  30.00   64
 21  ω     11.00 115.00   1.00    2.00    --   40.71  57.00-120.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0311192000
_diffrn_orient_matrix_UB_12      0.0851407000
_diffrn_orient_matrix_UB_13      0.0872451000
_diffrn_orient_matrix_UB_21      0.0852498000
_diffrn_orient_matrix_UB_22      0.1537439000
_diffrn_orient_matrix_UB_23      -0.0061805000
_diffrn_orient_matrix_UB_31      -0.0699919000
_diffrn_orient_matrix_UB_32      0.2248545000
_diffrn_orient_matrix_UB_33      -0.0287328000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2442
_reflns_number_total             2655
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+0.6307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0860
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9-C10
 1.374 with sigma of 0.001
 C9-C10A
 1.374 with sigma of 0.001
 C9-S2 \\sim S2-C12
 with sigma of 0.001
 C9-S2A \\sim S2A-C12A
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
C12 \\sim C11A \\sim C12A \\sim C11 \\sim C10 \\sim C10A: within 1.7A with
sigma of 0.005 and sigma for terminal atoms of 0.005
S2A \\sim S2: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.005
4. Others
 Sof(S2A)=Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(H11A)=Sof(C10A)=Sof(H10A)=1-FVAR(1)
 Sof(S2)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C2(H2A,H2B), C3(H3A,H3B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C12A(H12A),
 C11A(H11A), C10A(H10A)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.77835(3) 0.81124(7) 0.75117(2) 0.01831(12) Uani 1 1 d . . . . .
S2 S 0.97413(10) 0.5574(4) 0.80769(14) 0.0247(3) Uani 0.618(2) 1 d D U P A 1
O2 O 0.83206(8) 0.9803(2) 0.72252(6) 0.0238(3) Uani 1 1 d . . . . .
O1 O 0.72152(9) 0.9015(2) 0.79378(6) 0.0260(3) Uani 1 1 d . . . . .
N2 N 0.78051(10) 0.3884(2) 0.61019(7) 0.0214(3) Uani 1 1 d . . . . .
H2 H 0.7993 0.2792 0.6476 0.026 Uiso 1 1 calc R . . . .
N1 N 0.70046(9) 0.6630(2) 0.67279(7) 0.0185(3) Uani 1 1 d . . . . .
C5 C 0.73108(11) 0.6031(3) 0.61033(8) 0.0179(3) Uani 1 1 d . . . . .
C6 C 0.71416(11) 0.7290(3) 0.54060(8) 0.0211(3) Uani 1 1 d . . . . .
H6 H 0.6818 0.8803 0.5251 0.025 Uiso 1 1 calc R . . . .
C4 C 0.62766(11) 0.4942(3) 0.68514(9) 0.0210(3) Uani 1 1 d . . . . .
H4A H 0.6163 0.5474 0.7316 0.025 Uiso 1 1 calc R . . . .
H4B H 0.6544 0.3273 0.6950 0.025 Uiso 1 1 calc R . . . .
C2 C 0.47833(11) 0.7462(3) 0.59165(9) 0.0215(3) Uani 1 1 d . . . . .
H2A H 0.5236 0.8654 0.5845 0.026 Uiso 1 1 calc R . . . .
H2B H 0.4209 0.7330 0.5414 0.026 Uiso 1 1 calc R . . . .
C7 C 0.75559(12) 0.5834(3) 0.49689(9) 0.0239(3) Uani 1 1 d . . . . .
H7 H 0.7557 0.6223 0.4473 0.029 Uiso 1 1 calc R . . . .
C8 C 0.79531(12) 0.3756(3) 0.54075(9) 0.0240(3) Uani 1 1 d . . . . .
H8 H 0.8270 0.2475 0.5260 0.029 Uiso 1 1 calc R . . . .
C9 C 0.86484(11) 0.6015(3) 0.81325(8) 0.0200(3) Uani 1 1 d D . . . .
C3 C 0.52976(11) 0.4946(3) 0.61213(9) 0.0214(3) Uani 1 1 d . . . . .
H3A H 0.4850 0.3775 0.6210 0.026 Uiso 1 1 calc R . . . .
H3B H 0.5420 0.4366 0.5665 0.026 Uiso 1 1 calc R . . . .
C1 C 0.44477(13) 0.8422(3) 0.65544(10) 0.0266(4) Uani 1 1 d . . . . .
H1A H 0.4066 0.9910 0.6368 0.040 Uiso 1 1 calc GR . . . .
H1B H 0.5020 0.8771 0.7035 0.040 Uiso 1 1 calc GR . . . .
H1C H 0.4046 0.7189 0.6663 0.040 Uiso 1 1 calc GR . . . .
C10 C 0.8458(9) 0.4517(18) 0.8665(5) 0.0283(17) Uani 0.618(2) 1 d D U P A 1
H10 H 0.7888 0.4552 0.8771 0.034 Uiso 0.618(2) 1 calc R . P A 1
C11 C 0.9321(4) 0.2829(13) 0.9041(5) 0.0307(9) Uani 0.618(2) 1 d . U P A 1
H11 H 0.9360 0.1578 0.9403 0.037 Uiso 0.618(2) 1 calc R . P A 1
C12 C 1.0050(12) 0.3385(19) 0.8776(6) 0.0325(15) Uani 0.618(2) 1 d D U P A 1
H12 H 1.0666 0.2604 0.8971 0.039 Uiso 0.618(2) 1 calc R . P A 1
S2A S 0.8484(4) 0.4393(8) 0.8838(2) 0.0293(6) Uani 0.382(2) 1 d D U P A 2
C12A C 0.9577(5) 0.302(2) 0.9121(9) 0.0305(16) Uani 0.382(2) 1 d D U P A 2
H12A H 0.9816 0.1978 0.9563 0.037 Uiso 0.382(2) 1 calc R . P A 2
C11A C 1.010(2) 0.348(3) 0.8682(10) 0.0290(14) Uani 0.382(2) 1 d . U P A 2
H11A H 1.0690 0.2715 0.8733 0.035 Uiso 0.382(2) 1 calc R . P A 2
C10A C 0.9533(6) 0.555(3) 0.8066(9) 0.031(2) Uani 0.382(2) 1 d D U P A 2
H10A H 0.9758 0.6325 0.7714 0.037 Uiso 0.382(2) 1 calc R . 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 O2 1.4327(12) . ?
S1 O1 1.4320(11) . ?
S1 N1 1.6399(13) . ?
S1 C9 1.7403(15) . ?
S2 C9 1.663(2) . ?
S2 C12 1.663(2) . ?
N2 H2 0.8600 . ?
N2 C5 1.367(2) . ?
N2 C8 1.3690(19) . ?
N1 C5 1.4178(18) . ?
N1 C4 1.4866(19) . ?
C5 C6 1.374(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.417(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.521(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.525(2) . ?
C2 C1 1.523(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.366(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.3743(10) . ?
C9 S2A 1.651(3) . ?
C9 C10A 1.3742(11) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C11 1.486(11) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(14) . ?
C12 H12 0.9300 . ?
S2A C12A 1.652(3) . ?
C12A H12A 0.9300 . ?
C12A C11A 1.33(2) . ?
C11A H11A 0.9300 . ?
C11A C10A 1.567(15) . ?
C10A H10A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 N1 106.61(6) . . ?
O2 S1 C9 106.69(7) . . ?
O1 S1 O2 120.29(7) . . ?
O1 S1 N1 106.57(7) . . ?
O1 S1 C9 107.38(7) . . ?
N1 S1 C9 108.95(7) . . ?
C9 S2 C12 91.7(6) . . ?
C5 N2 H2 125.6 . . ?
C5 N2 C8 108.89(13) . . ?
C8 N2 H2 125.6 . . ?
C5 N1 S1 118.57(10) . . ?
C5 N1 C4 117.27(12) . . ?
C4 N1 S1 117.36(10) . . ?
N2 C5 N1 122.16(13) . . ?
N2 C5 C6 108.51(13) . . ?
C6 C5 N1 129.24(14) . . ?
C5 C6 H6 126.7 . . ?
C5 C6 C7 106.68(14) . . ?
C7 C6 H6 126.7 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 C3 110.56(12) . . ?
H4A C4 H4B 108.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C1 C2 C3 113.20(13) . . ?
C6 C7 H7 126.2 . . ?
C8 C7 C6 107.68(13) . . ?
C8 C7 H7 126.2 . . ?
N2 C8 H8 125.9 . . ?
C7 C8 N2 108.24(14) . . ?
C7 C8 H8 125.9 . . ?
S2 C9 S1 121.59(12) . . ?
C10 C9 S1 122.8(5) . . ?
C10 C9 S2 115.5(6) . . ?
S2A C9 S1 123.8(2) . . ?
C10A C9 S1 122.1(7) . . ?
C10A C9 S2A 114.1(8) . . ?
C4 C3 C2 114.71(13) . . ?
C4 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C9 C10 H10 125.9 . . ?
C9 C10 C11 108.1(8) . . ?
C11 C10 H10 125.9 . . ?
C10 C11 H11 124.9 . . ?
C12 C11 C10 110.1(8) . . ?
C12 C11 H11 124.9 . . ?
S2 C12 H12 122.8 . . ?
C11 C12 S2 114.4(10) . . ?
C11 C12 H12 122.8 . . ?
C9 S2A C12A 93.2(6) . . ?
S2A C12A H12A 121.7 . . ?
C11A C12A S2A 116.6(13) . . ?
C11A C12A H12A 121.7 . . ?
C12A C11A H11A 126.4 . . ?
C12A C11A C10A 107.2(17) . . ?
C10A C11A H11A 126.4 . . ?
C9 C10A C11A 108.4(14) . . ?
C9 C10A H10A 125.8 . . ?
C11A C10A H10A 125.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C5 N2 88.03(16) . . . . ?
S1 N1 C5 C6 -95.92(17) . . . . ?
S1 N1 C4 C3 145.93(11) . . . . ?
S1 C9 C10 C11 175.2(4) . . . . ?
S1 C9 S2A C12A -179.4(4) . . . . ?
S1 C9 C10A C11A -177.1(11) . . . . ?
S2 C9 C10 C11 -1.1(8) . . . . ?
O2 S1 N1 C5 36.06(13) . . . . ?
O2 S1 N1 C4 -173.57(11) . . . . ?
O2 S1 C9 S2 -20.39(15) . . . . ?
O2 S1 C9 C10 163.5(6) . . . . ?
O2 S1 C9 S2A 157.2(2) . . . . ?
O2 S1 C9 C10A -23.7(8) . . . . ?
O1 S1 N1 C5 165.70(11) . . . . ?
O1 S1 N1 C4 -43.93(12) . . . . ?
O1 S1 C9 S2 -150.61(13) . . . . ?
O1 S1 C9 C10 33.3(6) . . . . ?
O1 S1 C9 S2A 27.0(2) . . . . ?
O1 S1 C9 C10A -153.9(8) . . . . ?
N2 C5 C6 C7 -0.19(17) . . . . ?
N1 S1 C9 S2 94.34(14) . . . . ?
N1 S1 C9 C10 -81.8(6) . . . . ?
N1 S1 C9 S2A -88.0(2) . . . . ?
N1 S1 C9 C10A 91.1(8) . . . . ?
N1 C5 C6 C7 -176.66(14) . . . . ?
N1 C4 C3 C2 -60.88(17) . . . . ?
C5 N2 C8 C7 0.30(18) . . . . ?
C5 N1 C4 C3 -63.31(17) . . . . ?
C5 C6 C7 C8 0.37(17) . . . . ?
C6 C7 C8 N2 -0.41(18) . . . . ?
C4 N1 C5 N2 -62.36(18) . . . . ?
C4 N1 C5 C6 113.69(17) . . . . ?
C8 N2 C5 N1 176.71(13) . . . . ?
C8 N2 C5 C6 -0.06(17) . . . . ?
C9 S1 N1 C5 -78.73(13) . . . . ?
C9 S1 N1 C4 71.64(12) . . . . ?
C9 S2 C12 C11 3.3(10) . . . . ?
C9 C10 C11 C12 3.4(11) . . . . ?
C9 S2A C12A C11A -5.5(14) . . . . ?
C1 C2 C3 C4 -64.93(17) . . . . ?
C10 C11 C12 S2 -4.4(12) . . . . ?
C12 S2 C9 S1 -177.5(5) . . . . ?
C12 S2 C9 C10 -1.1(8) . . . . ?
S2A C9 C10A C11A 2.1(16) . . . . ?
S2A C12A C11A C10A 7(2) . . . . ?
C12A C11A C10A C9 -6(2) . . . . ?
C10A C9 S2A C12A 1.5(9) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-06-21
_olex2_date_sample_submission    2016-06-15
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with inert oil'
_olex2_submission_original_sample_id AM-1269(AM-III-021),F.3-5
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.056
_oxdiff_exptl_absorpt_empirical_full_min 0.641
