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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_7336
_database_code_depnum_ccdc_archive 'CCDC 1033418'
_audit_update_record             
;
2014-11-10 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;
_audit_creation_date             2014-07-08
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H18 N2 O3 S'
_chemical_formula_sum            'C23 H18 N2 O3 S'
_chemical_formula_weight         402.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.4496(6)
_cell_length_b                   10.2550(5)
_cell_length_c                   11.2370(6)
_cell_angle_alpha                102.651(4)
_cell_angle_beta                 93.971(5)
_cell_angle_gamma                114.471(5)
_cell_volume                     951.22(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4151
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      72.4540
_cell_measurement_theta_min      4.9120
_exptl_absorpt_coefficient_mu    1.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6105
_diffrn_reflns_theta_full        73.32
_diffrn_reflns_theta_max         73.32
_diffrn_reflns_theta_min         4.10
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9670
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3992   38.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3992   38.0000  -60.0000 85

#__ type_ start__ end____ width___ exp.time_
  3 omega  -81.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3992   19.0000 -120.0000 100

#__ type_ start__ end____ width___ exp.time_
  4 omega   25.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3992 -125.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
  5 omega   51.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -94.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  6 omega   91.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122 -125.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -45.0000   90.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega  119.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122   30.0000  150.0000 57

#__ type_ start__ end____ width___ exp.time_
  9 omega   93.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122   30.0000   90.0000 85

#__ type_ start__ end____ width___ exp.time_
 10 omega  138.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  125.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
 11 omega   97.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  125.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   77.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122   30.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   30.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -30.0000  150.0000 61

#__ type_ start__ end____ width___ exp.time_
 14 omega   39.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -77.0000  -30.0000 102

#__ type_ start__ end____ width___ exp.time_
 15 omega   40.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3992 -125.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 16 omega   25.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -94.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122 -125.0000  -30.0000 74

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -30.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   29.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9122  -30.0000  -30.0000 48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1240947000
_diffrn_orient_matrix_UB_12      0.0550931000
_diffrn_orient_matrix_UB_13      0.0361147000
_diffrn_orient_matrix_UB_21      0.0936896000
_diffrn_orient_matrix_UB_22      0.0734843000
_diffrn_orient_matrix_UB_23      0.1336079000
_diffrn_orient_matrix_UB_31      0.0947771000
_diffrn_orient_matrix_UB_32      0.1449042000
_diffrn_orient_matrix_UB_33      -0.0353497000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           n/a
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3536
_reflns_number_total             3694
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         1.200
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3694
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.152
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.7470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1273
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.18669(5) -0.08880(5) 0.22719(4) 0.02260(15) Uani 1 1 d . . .
C18 C 0.4711(2) 0.1331(2) 0.22073(17) 0.0249(4) Uani 1 1 d . . .
H18 H 0.5002 0.1357 0.3023 0.030 Uiso 1 1 calc R . .
O16 O -0.24740(17) 0.28647(17) 0.43356(13) 0.0346(4) Uani 1 1 d . . .
C6 C 0.1267(2) 0.02760(19) 0.33025(16) 0.0188(4) Uani 1 1 d . . .
C22 C 0.2800(2) 0.0229(2) 0.03021(17) 0.0261(4) Uani 1 1 d . . .
H22 H 0.1809 -0.0467 -0.0148 0.031 Uiso 1 1 calc R . .
O13 O 0.27109(18) -0.14418(16) 0.29810(13) 0.0313(3) Uani 1 1 d . . .
O12 O 0.05079(17) -0.19417(15) 0.13436(13) 0.0299(3) Uani 1 1 d . . .
C21 C 0.3872(2) 0.1201(2) -0.02464(18) 0.0276(4) Uani 1 1 d . . .
H21 H 0.3601 0.1137 -0.1076 0.033 Uiso 1 1 calc R . .
N14 N -0.02279(17) 0.31770(17) 0.54722(13) 0.0216(3) Uani 1 1 d . . .
H14 H 0.0424 0.3693 0.6159 0.026 Uiso 1 1 calc R . .
C4 C 0.3461(2) 0.1103(2) 0.51472(17) 0.0250(4) Uani 1 1 d . . .
H4 H 0.3878 0.0484 0.4749 0.030 Uiso 1 1 calc R . .
C20 C 0.5351(2) 0.2274(2) 0.04225(18) 0.0257(4) Uani 1 1 d . . .
C7 C -0.0060(2) 0.03774(19) 0.28355(15) 0.0192(4) Uani 1 1 d . . .
H7 H -0.0599 -0.0199 0.2039 0.023 Uiso 1 1 calc R . .
N1 N 0.22459(18) 0.29744(18) 0.63907(14) 0.0249(4) Uani 1 1 d . . .
C10 C 0.1544(2) 0.20880(19) 0.52166(15) 0.0193(4) Uani 1 1 d . . .
C17 C 0.3225(2) 0.0309(2) 0.15355(17) 0.0220(4) Uani 1 1 d . . .
C9 C 0.0166(2) 0.21826(19) 0.46962(15) 0.0183(4) Uani 1 1 d . . .
C5 C 0.2108(2) 0.1128(2) 0.45332(16) 0.0195(4) Uani 1 1 d . . .
C19 C 0.5754(2) 0.2310(2) 0.16525(18) 0.0269(4) Uani 1 1 d . . .
H19 H 0.6743 0.3006 0.2106 0.032 Uiso 1 1 calc R . .
C15 C -0.1512(2) 0.3452(2) 0.52965(17) 0.0233(4) Uani 1 1 d . . .
C24 C -0.1645(2) 0.4539(2) 0.6355(2) 0.0294(4) Uani 1 1 d . . .
C2 C 0.3502(2) 0.2915(2) 0.69087(17) 0.0294(4) Uani 1 1 d . . .
H2 H 0.3990 0.3521 0.7707 0.035 Uiso 1 1 calc R . .
C23 C 0.6491(3) 0.3377(3) -0.0158(2) 0.0343(5) Uani 1 1 d . . .
H23A H 0.6344 0.2928 -0.1030 0.051 Uiso 1 1 calc R . .
H23B H 0.7555 0.3663 0.0223 0.051 Uiso 1 1 calc R . .
H23C H 0.6298 0.4241 -0.0037 0.051 Uiso 1 1 calc R . .
C8 C -0.0624(2) 0.13178(19) 0.35178(15) 0.0183(3) Uani 1 1 d . . .
H8 H -0.1526 0.1358 0.3178 0.022 Uiso 1 1 calc R . .
C25 C -0.0745(3) 0.5030(2) 0.7539(2) 0.0366(5) Uani 1 1 d . . .
H25 H 0.0010 0.4701 0.7699 0.044 Uiso 1 1 calc R . .
C26 C -0.0976(4) 0.6012(2) 0.8479(3) 0.0539(8) Uani 1 1 d . . .
H26 H -0.0368 0.6347 0.9266 0.065 Uiso 1 1 calc R . .
C3 C 0.4144(2) 0.1990(2) 0.63228(18) 0.0294(4) Uani 1 1 d . . .
H3 H 0.5028 0.1981 0.6732 0.035 Uiso 1 1 calc R . .
C29 C -0.2785(3) 0.5035(2) 0.6127(3) 0.0404(6) Uani 1 1 d . . .
H29 H -0.3396 0.4714 0.5342 0.048 Uiso 1 1 calc R . .
C28 C -0.2993(4) 0.6013(3) 0.7090(3) 0.0584(9) Uani 1 1 d . . .
H28 H -0.3749 0.6345 0.6942 0.070 Uiso 1 1 calc R . .
C27 C -0.2108(4) 0.6494(3) 0.8248(3) 0.0681(11) Uani 1 1 d . . .
H27 H -0.2266 0.7146 0.8882 0.082 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
S11 C6 1.7702(18) . ?
S11 O13 1.4419(14) . ?
S11 O12 1.4408(15) . ?
S11 C17 1.7678(18) . ?
C18 C17 1.389(3) . ?
C18 C19 1.381(3) . ?
O16 C15 1.217(2) . ?
C6 C7 1.378(2) . ?
C6 C5 1.432(2) . ?
C22 C21 1.385(3) . ?
C22 C17 1.391(3) . ?
C21 C20 1.395(3) . ?
N14 C9 1.382(2) . ?
N14 C15 1.366(2) . ?
C4 C5 1.423(2) . ?
C4 C3 1.363(3) . ?
C20 C19 1.396(3) . ?
C20 C23 1.509(3) . ?
C7 C8 1.400(3) . ?
N1 C10 1.364(2) . ?
N1 C2 1.316(3) . ?
C10 C9 1.439(2) . ?
C10 C5 1.416(3) . ?
C9 C8 1.378(2) . ?
C15 C24 1.493(3) . ?
C24 C25 1.393(3) . ?
C24 C29 1.399(3) . ?
C2 C3 1.400(3) . ?
C25 C26 1.387(3) . ?
C26 C27 1.382(5) . ?
C29 C28 1.390(3) . ?
C28 C27 1.365(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O13 S11 C6 109.02(8) . . ?
O13 S11 C17 107.80(9) . . ?
O12 S11 C6 107.80(8) . . ?
O12 S11 O13 118.76(9) . . ?
O12 S11 C17 107.84(9) . . ?
C17 S11 C6 104.76(8) . . ?
C19 C18 C17 119.35(17) . . ?
C7 C6 S11 115.82(13) . . ?
C7 C6 C5 120.26(16) . . ?
C5 C6 S11 123.87(14) . . ?
C21 C22 C17 119.12(18) . . ?
C22 C21 C20 121.21(17) . . ?
C15 N14 C9 128.76(15) . . ?
C3 C4 C5 119.68(19) . . ?
C21 C20 C19 118.32(18) . . ?
C21 C20 C23 121.23(17) . . ?
C19 C20 C23 120.45(19) . . ?
C6 C7 C8 122.29(16) . . ?
C2 N1 C10 117.78(17) . . ?
N1 C10 C9 115.64(16) . . ?
N1 C10 C5 123.30(16) . . ?
C5 C10 C9 121.05(15) . . ?
C18 C17 S11 119.09(14) . . ?
C18 C17 C22 120.71(17) . . ?
C22 C17 S11 120.20(15) . . ?
N14 C9 C10 114.17(15) . . ?
C8 C9 N14 126.28(16) . . ?
C8 C9 C10 119.55(16) . . ?
C4 C5 C6 126.41(17) . . ?
C10 C5 C6 117.31(16) . . ?
C10 C5 C4 116.28(16) . . ?
C18 C19 C20 121.22(19) . . ?
O16 C15 N14 122.28(17) . . ?
O16 C15 C24 122.15(18) . . ?
N14 C15 C24 115.56(17) . . ?
C25 C24 C15 123.75(19) . . ?
C25 C24 C29 119.5(2) . . ?
C29 C24 C15 116.7(2) . . ?
N1 C2 C3 123.56(17) . . ?
C9 C8 C7 119.51(16) . . ?
C26 C25 C24 120.0(3) . . ?
C27 C26 C25 120.2(3) . . ?
C4 C3 C2 119.40(18) . . ?
C28 C29 C24 119.1(3) . . ?
C27 C28 C29 121.2(3) . . ?
C28 C27 C26 119.9(2) . . ?

####################################################################### 
# 
# 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_ss
_database_code_depnum_ccdc_archive 'CCDC 1408003'
_audit_update_record             
;
2015-06-22 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 N2 O4 S'
_chemical_formula_weight         432.48

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_space_group_name_Hall           '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.261(5)
_cell_length_b                   9.440(5)
_cell_length_c                   15.434(5)
_cell_angle_alpha                92.805(5)
_cell_angle_beta                 95.279(5)
_cell_angle_gamma                96.848(5)
_cell_volume                     1044.0(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       CRYSR_01
_exptl_crystal_colour            'red color'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9488
_exptl_absorpt_correction_T_max  0.9631
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7454
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4496
_reflns_number_gt                3801
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0655P)²+0.1632P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4496
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.72266(6) 0.59313(4) 0.76798(2) 0.03874(13) Uani 1 1 d . . .
O2 O 0.81185(19) 0.73800(12) 0.77464(8) 0.0516(3) Uani 1 1 d . . .
O3 O 0.86274(17) 0.66178(12) 0.45031(7) 0.0475(3) Uani 1 1 d . . .
N2 N 0.5547(2) 0.30079(13) 0.68970(8) 0.0378(3) Uani 1 1 d . . .
O4 O 0.75208(17) 0.13184(14) 0.69496(9) 0.0536(3) Uani 1 1 d . . .
N1 N 0.56465(19) 0.20629(14) 0.51815(9) 0.0417(3) Uani 1 1 d . . .
O1 O 0.53672(16) 0.56496(13) 0.79318(8) 0.0489(3) Uani 1 1 d . . .
C11 C 0.7228(2) 0.43690(16) 0.48408(9) 0.0348(3) Uani 1 1 d . . .
C5 C 0.8663(2) 0.49005(17) 0.83002(9) 0.0395(3) Uani 1 1 d . . .
C19 C 0.4689(2) 0.08726(15) 0.76258(9) 0.0361(3) Uani 1 1 d . . .
C8 C 0.7234(2) 0.52777(15) 0.65755(9) 0.0342(3) Uani 1 1 d . . .
C9 C 0.7979(2) 0.62438(15) 0.59941(10) 0.0365(3) Uani 1 1 d . . .
H9 H 0.8472 0.7171 0.6190 0.044 Uiso 1 1 calc R . .
C12 C 0.6460(2) 0.34231(15) 0.54292(9) 0.0346(3) Uani 1 1 d . . .
C20 C 0.2791(2) 0.09437(17) 0.74859(11) 0.0435(4) Uani 1 1 d . . .
H20 H 0.2352 0.1586 0.7103 0.052 Uiso 1 1 calc R . .
C18 C 0.6063(2) 0.17277(16) 0.71268(10) 0.0374(3) Uani 1 1 d . . .
C10 C 0.7967(2) 0.57984(16) 0.51360(9) 0.0359(3) Uani 1 1 d . . .
C24 C 0.5331(3) -0.00752(18) 0.82084(11) 0.0453(4) Uani 1 1 d . . .
H24 H 0.6601 -0.0140 0.8306 0.054 Uiso 1 1 calc R . .
C13 C 0.6464(2) 0.39039(15) 0.63213(9) 0.0341(3) Uani 1 1 d . . .
C14 C 0.7186(2) 0.38505(19) 0.39618(10) 0.0440(4) Uani 1 1 d . . .
H14 H 0.7683 0.4435 0.3551 0.053 Uiso 1 1 calc R . .
C23 C 0.4073(3) -0.09243(19) 0.86440(12) 0.0537(4) Uani 1 1 d . . .
H23 H 0.4505 -0.1545 0.9043 0.064 Uiso 1 1 calc R . .
C16 C 0.5641(3) 0.16341(18) 0.43557(11) 0.0485(4) Uani 1 1 d . . .
H16 H 0.5096 0.0711 0.4179 0.058 Uiso 1 1 calc R . .
C21 C 0.1545(3) 0.0072(2) 0.79077(12) 0.0522(4) Uani 1 1 d . . .
H21 H 0.0272 0.0111 0.7799 0.063 Uiso 1 1 calc R . .
C7 C 1.1702(3) 0.4375(3) 0.87896(13) 0.0612(5) Uani 1 1 d . . .
H7 H 1.2987 0.4546 0.8777 0.073 Uiso 1 1 calc R . .
C2 C 1.0969(3) 0.3344(2) 0.93144(11) 0.0569(5) Uani 1 1 d . . .
C17 C 0.9341(3) 0.8078(2) 0.47409(14) 0.0513(4) Uani 1 1 d . . .
C4 C 0.7894(3) 0.38770(19) 0.88198(11) 0.0496(4) Uani 1 1 d . . .
H4 H 0.6609 0.3707 0.8833 0.060 Uiso 1 1 calc R . .
C15 C 0.6411(3) 0.2488(2) 0.37261(11) 0.0505(4) Uani 1 1 d . . .
H15 H 0.6391 0.2124 0.3154 0.061 Uiso 1 1 calc R . .
C22 C 0.2196(3) -0.08567(19) 0.84909(12) 0.0535(4) Uani 1 1 d . . .
H22 H 0.1361 -0.1439 0.8781 0.064 Uiso 1 1 calc R . .
C6 C 1.0574(3) 0.5154(2) 0.82851(11) 0.0517(4) Uani 1 1 d . . .
H6 H 1.1093 0.5843 0.7938 0.062 Uiso 1 1 calc R . .
C3 C 0.9058(3) 0.3109(2) 0.93198(11) 0.0579(5) Uani 1 1 d . . .
H3 H 0.8541 0.2420 0.9667 0.069 Uiso 1 1 calc R . .
C1 C 1.2237(4) 0.2517(3) 0.98665(14) 0.0810(7) Uani 1 1 d . . .
H1A H 1.3510 0.2824 0.9777 0.121 Uiso 1 1 calc R . .
H1B H 1.1947 0.1515 0.9704 0.121 Uiso 1 1 calc R . .
H1C H 1.2061 0.2685 1.0470 0.121 Uiso 1 1 calc R . .
H2 H 0.472(3) 0.334(2) 0.7131(14) 0.059(6) Uiso 1 1 d . . .
H25 H 1.035(3) 0.816(2) 0.5242(14) 0.057(6) Uiso 1 1 d . . .
H26 H 0.998(3) 0.837(2) 0.4254(15) 0.069(6) Uiso 1 1 d . . .
H27 H 0.833(3) 0.861(2) 0.4874(13) 0.055(5) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.4363(14) . ?
S1 O1 1.4374(15) . ?
S1 C5 1.7611(17) . ?
S1 C8 1.7847(15) . ?
O3 C10 1.3616(18) . ?
O3 C17 1.431(2) . ?
N2 C18 1.361(2) . ?
N2 C13 1.4130(19) . ?
N2 H2 0.81(2) . ?
O4 C18 1.218(2) . ?
N1 C16 1.318(2) . ?
N1 C12 1.369(2) . ?
C11 C12 1.410(2) . ?
C11 C14 1.416(2) . ?
C11 C10 1.428(2) . ?
C5 C6 1.382(3) . ?
C5 C4 1.385(2) . ?
C19 C20 1.385(2) . ?
C19 C24 1.388(2) . ?
C19 C18 1.500(2) . ?
C8 C13 1.373(2) . ?
C8 C9 1.408(2) . ?
C9 C10 1.369(2) . ?
C9 H9 0.9300 . ?
C12 C13 1.428(2) . ?
C20 C21 1.379(2) . ?
C20 H20 0.9300 . ?
C24 C23 1.386(3) . ?
C24 H24 0.9300 . ?
C14 C15 1.359(2) . ?
C14 H14 0.9300 . ?
C23 C22 1.371(3) . ?
C23 H23 0.9300 . ?
C16 C15 1.406(3) . ?
C16 H16 0.9300 . ?
C21 C22 1.379(3) . ?
C21 H21 0.9300 . ?
C7 C6 1.378(3) . ?
C7 C2 1.386(3) . ?
C7 H7 0.9300 . ?
C2 C3 1.379(3) . ?
C2 C1 1.509(3) . ?
C17 H25 1.01(2) . ?
C17 H26 0.95(2) . ?
C17 H27 0.97(2) . ?
C4 C3 1.384(3) . ?
C4 H4 0.9300 . ?
C15 H15 0.9300 . ?
C22 H22 0.9300 . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
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 118.73(8) . . ?
O2 S1 C5 107.91(9) . . ?
O1 S1 C5 108.14(8) . . ?
O2 S1 C8 107.02(7) . . ?
O1 S1 C8 108.82(7) . . ?
C5 S1 C8 105.46(7) . . ?
C10 O3 C17 117.90(13) . . ?
C18 N2 C13 124.44(14) . . ?
C18 N2 H2 119.8(15) . . ?
C13 N2 H2 115.5(15) . . ?
C16 N1 C12 117.16(14) . . ?
C12 C11 C14 117.40(14) . . ?
C12 C11 C10 119.96(13) . . ?
C14 C11 C10 122.62(14) . . ?
C6 C5 C4 120.22(16) . . ?
C6 C5 S1 119.29(13) . . ?
C4 C5 S1 120.46(14) . . ?
C20 C19 C24 119.14(15) . . ?
C20 C19 C18 121.86(14) . . ?
C24 C19 C18 118.90(15) . . ?
C13 C8 C9 123.07(14) . . ?
C13 C8 S1 119.81(11) . . ?
C9 C8 S1 117.07(11) . . ?
C10 C9 C8 119.01(14) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
N1 C12 C11 122.99(13) . . ?
N1 C12 C13 117.71(13) . . ?
C11 C12 C13 119.27(13) . . ?
C21 C20 C19 120.74(16) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
O4 C18 N2 122.95(14) . . ?
O4 C18 C19 122.99(14) . . ?
N2 C18 C19 114.05(14) . . ?
O3 C10 C9 125.29(14) . . ?
O3 C10 C11 114.46(13) . . ?
C9 C10 C11 120.25(13) . . ?
C23 C24 C19 119.74(17) . . ?
C23 C24 H24 120.1 . . ?
C19 C24 H24 120.1 . . ?
C8 C13 N2 121.83(13) . . ?
C8 C13 C12 118.41(13) . . ?
N2 C13 C12 119.54(13) . . ?
C15 C14 C11 119.15(15) . . ?
C15 C14 H14 120.4 . . ?
C11 C14 H14 120.4 . . ?
C22 C23 C24 120.51(17) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
N1 C16 C15 123.92(16) . . ?
N1 C16 H16 118.0 . . ?
C15 C16 H16 118.0 . . ?
C22 C21 C20 119.72(18) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C6 C7 C2 121.64(19) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
C3 C2 C7 118.07(17) . . ?
C3 C2 C1 121.4(2) . . ?
C7 C2 C1 120.5(2) . . ?
O3 C17 H25 111.7(11) . . ?
O3 C17 H26 103.6(14) . . ?
H25 C17 H26 104.5(18) . . ?
O3 C17 H27 109.9(12) . . ?
H25 C17 H27 111.3(17) . . ?
H26 C17 H27 115.5(18) . . ?
C3 C4 C5 119.31(18) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C14 C15 C16 119.35(15) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C23 C22 C21 120.12(17) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C7 C6 C5 119.32(18) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C2 C3 C4 121.45(18) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C5 C6 -39.77(15) . . . . ?
O1 S1 C5 C6 -169.38(13) . . . . ?
C8 S1 C5 C6 74.34(14) . . . . ?
O2 S1 C5 C4 138.19(14) . . . . ?
O1 S1 C5 C4 8.58(15) . . . . ?
C8 S1 C5 C4 -107.70(14) . . . . ?
O2 S1 C8 C13 179.90(12) . . . . ?
O1 S1 C8 C13 -50.64(14) . . . . ?
C5 S1 C8 C13 65.18(15) . . . . ?
O2 S1 C8 C9 -2.68(14) . . . . ?
O1 S1 C8 C9 126.77(12) . . . . ?
C5 S1 C8 C9 -117.41(13) . . . . ?
C13 C8 C9 C10 -1.0(2) . . . . ?
S1 C8 C9 C10 -178.29(11) . . . . ?
C16 N1 C12 C11 1.7(2) . . . . ?
C16 N1 C12 C13 179.62(14) . . . . ?
C14 C11 C12 N1 -1.8(2) . . . . ?
C10 C11 C12 N1 176.73(14) . . . . ?
C14 C11 C12 C13 -179.70(13) . . . . ?
C10 C11 C12 C13 -1.2(2) . . . . ?
C24 C19 C20 C21 -1.0(2) . . . . ?
C18 C19 C20 C21 175.36(15) . . . . ?
C13 N2 C18 O4 10.2(2) . . . . ?
C13 N2 C18 C19 -170.39(13) . . . . ?
C20 C19 C18 O4 -148.85(16) . . . . ?
C24 C19 C18 O4 27.5(2) . . . . ?
C20 C19 C18 N2 31.8(2) . . . . ?
C24 C19 C18 N2 -151.89(15) . . . . ?
C17 O3 C10 C9 -2.1(2) . . . . ?
C17 O3 C10 C11 178.17(15) . . . . ?
C8 C9 C10 O3 179.55(14) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C12 C11 C10 O3 -178.48(13) . . . . ?
C14 C11 C10 O3 0.0(2) . . . . ?
C12 C11 C10 C9 1.8(2) . . . . ?
C14 C11 C10 C9 -179.79(14) . . . . ?
C20 C19 C24 C23 -0.5(2) . . . . ?
C18 C19 C24 C23 -176.90(15) . . . . ?
C9 C8 C13 N2 -173.03(14) . . . . ?
S1 C8 C13 N2 4.2(2) . . . . ?
C9 C8 C13 C12 1.5(2) . . . . ?
S1 C8 C13 C12 178.78(11) . . . . ?
C18 N2 C13 C8 -120.75(17) . . . . ?
C18 N2 C13 C12 64.7(2) . . . . ?
N1 C12 C13 C8 -178.44(13) . . . . ?
C11 C12 C13 C8 -0.4(2) . . . . ?
N1 C12 C13 N2 -3.8(2) . . . . ?
C11 C12 C13 N2 174.26(13) . . . . ?
C12 C11 C14 C15 0.3(2) . . . . ?
C10 C11 C14 C15 -178.15(15) . . . . ?
C19 C24 C23 C22 1.3(3) . . . . ?
C12 N1 C16 C15 -0.1(3) . . . . ?
C19 C20 C21 C22 1.5(3) . . . . ?
C6 C7 C2 C3 0.1(3) . . . . ?
C6 C7 C2 C1 -179.43(18) . . . . ?
C6 C5 C4 C3 -0.3(3) . . . . ?
S1 C5 C4 C3 -178.19(13) . . . . ?
C11 C14 C15 C16 1.1(3) . . . . ?
N1 C16 C15 C14 -1.3(3) . . . . ?
C24 C23 C22 C21 -0.8(3) . . . . ?
C20 C21 C22 C23 -0.7(3) . . . . ?
C2 C7 C6 C5 -0.2(3) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
S1 C5 C6 C7 178.19(14) . . . . ?
C7 C2 C3 C4 -0.1(3) . . . . ?
C1 C2 C3 C4 179.40(18) . . . . ?
C5 C4 C3 C2 0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.939
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.939
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.038
