# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_MB-PVK-VV-27A
_database_code_depnum_ccdc_archive 'CCDC 1060438'
_audit_update_record             
;
2015-04-18 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;
_audit_creation_date             2015-04-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_formula_moiety         'C25 H22 N2 O5 S'
_chemical_formula_sum            'C25 H22 N2 O5 S'
_chemical_formula_weight         462.53
_chemical_oxdiff_formula         'C25 H22 N2 O5 S1'
_chemical_oxdiff_usercomment     '298K, COLORLESS, 0.35 0.2 0.2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.1205(7)
_cell_length_b                   22.1481(18)
_cell_length_c                   11.2162(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.140(8)
_cell_angle_gamma                90
_cell_volume                     2230.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4005
_cell_measurement_theta_max      29.1043
_cell_measurement_theta_min      3.5657
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.3774
_exptl_crystal_F_000             968.9877
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_av_unetI/netI     0.0985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15406
_diffrn_reflns_theta_full        29.1686
_diffrn_reflns_theta_max         29.17
_diffrn_reflns_theta_min         3.57
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.8760
_diffrn_measured_fraction_theta_max 0.8760
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00    5.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -88.00  -63.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -92.00  -33.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  178.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
  4 omega  -86.00   27.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -19.0000   60.0000 113

#__ type_ start__ end____ width___ exp.time_
  5 omega  -74.00  -48.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  178.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   -7.00   19.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  106.0000   66.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  -22.00    5.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega  -23.00   24.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000   90.0000 47

#__ type_ start__ end____ width___ exp.time_
  9 omega  -84.00  -58.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000 -180.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0170499000
_diffrn_orient_matrix_UB_12      -0.0299818000
_diffrn_orient_matrix_UB_13      -0.0200820000
_diffrn_orient_matrix_UB_21      0.0025509000
_diffrn_orient_matrix_UB_22      0.0088967000
_diffrn_orient_matrix_UB_23      -0.0603565000
_diffrn_orient_matrix_UB_31      0.0770765000
_diffrn_orient_matrix_UB_32      -0.0068913000
_diffrn_orient_matrix_UB_33      0.0091824000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -12
_reflns_limit_k_max              30
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              -7
_reflns_number_gt                3039
_reflns_number_total             5286
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.8194
_refine_diff_density_min         -0.6660
_refine_diff_density_rms         0.1232
_refine_ls_d_res_high            0.7291
_refine_ls_d_res_low             5.7024
_refine_ls_goodness_of_fit_ref   1.0250
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    39
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.0250
_refine_ls_shift/su_max          0.5249
_refine_ls_shift/su_mean         0.0104
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0581P)²+0.0423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1605
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b)
2.c Aromatic/amide H refined with riding coordinates:
 C32(H32), C9(H9), C31(H31), C8(H8), C7(H7), C15(H15), C28(H28), C6(H6),
 C29(H29), C16(H16), C18(H18), C19(H19), C17(H17)
2.d Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c), C33(H33a,H33b,H33c)
;
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_refinement_flags_posn
S20 S 0.12004(8) 0.61573(3) 0.73198(6) 0.0374(2) Uani 1.000000 .
O22 O 0.1994(2) 0.58125(9) 0.65622(19) 0.0521(5) Uani 1.000000 .
O21 O -0.03702(19) 0.62550(9) 0.69780(18) 0.0475(5) Uani 1.000000 .
O24 O 0.0839(2) 0.69428(9) 0.48478(18) 0.0471(5) Uani 1.000000 .
O26 O -0.1332(2) 0.74053(9) 0.49144(18) 0.0510(5) Uani 1.000000 .
O2 O 0.1178(2) 0.86826(9) 0.55276(19) 0.0511(5) Uani 1.000000 .
N11 N 0.1955(2) 0.68375(9) 0.74878(19) 0.0327(5) Uani 1.000000 .
N3 N 0.2580(3) 0.83817(11) 0.5674(2) 0.0472(6) Uani 1.000000 .
C23 C -0.0018(3) 0.73436(12) 0.5276(2) 0.0361(6) Uani 1.000000 .
C10 C 0.3422(3) 0.69489(11) 0.7229(2) 0.0330(6) Uani 1.000000 .
C5 C 0.3660(3) 0.74385(12) 0.6515(2) 0.0361(6) Uani 1.000000 .
C4 C 0.2425(3) 0.78539(12) 0.6101(2) 0.0363(6) Uani 1.000000 .
C32 C 0.0622(3) 0.59755(12) 0.9594(3) 0.0432(7) Uani 1.000000 .
H32 H -0.0151(3) 0.62506(12) 0.9384(3) 0.0519(8) Uiso 1.000000 R
C27 C 0.1515(3) 0.58259(11) 0.8769(3) 0.0356(6) Uani 1.000000 .
C9 C 0.4615(3) 0.65831(13) 0.7731(3) 0.0433(7) Uani 1.000000 .
H9 H 0.4469(3) 0.62656(13) 0.8240(3) 0.0520(9) Uiso 1.000000 R
C1 C 0.0241(3) 0.83723(12) 0.6255(3) 0.0400(7) Uani 1.000000 .
H1 H -0.0788(3) 0.83697(12) 0.5817(3) 0.0480(8) Uiso 1.000000 R
C12 C 0.1006(3) 0.73728(11) 0.7510(2) 0.0322(6) Uani 1.000000 .
H12a H 0.0026(3) 0.72490(11) 0.7639(2) 0.0386(7) Uiso 1.000000 R
H12b H 0.1434(3) 0.76340(11) 0.8175(2) 0.0386(7) Uiso 1.000000 R
C14 C 0.0290(3) 0.86750(12) 0.7472(3) 0.0390(7) Uani 1.000000 .
C13 C 0.0866(3) 0.77203(11) 0.6309(2) 0.0324(6) Uani 1.000000 .
C30 C 0.2012(3) 0.53034(13) 1.1070(3) 0.0480(8) Uani 1.000000 .
C31 C 0.0870(3) 0.57189(13) 1.0728(3) 0.0509(8) Uani 1.000000 .
H31 H 0.0262(3) 0.58253(13) 1.1279(3) 0.0611(9) Uiso 1.000000 R
C8 C 0.6008(3) 0.66928(15) 0.7472(3) 0.0535(8) Uani 1.000000 .
H8 H 0.6799(3) 0.64457(15) 0.7806(3) 0.0642(10) Uiso 1.000000 R
C7 C 0.6254(3) 0.71621(16) 0.6727(3) 0.0557(9) Uani 1.000000 .
H7 H 0.7196(3) 0.72251(16) 0.6540(3) 0.0669(10) Uiso 1.000000 R
C15 C -0.0762(3) 0.85288(13) 0.8173(3) 0.0489(8) Uani 1.000000 .
H15 H -0.1507(3) 0.82525(13) 0.7881(3) 0.0587(9) Uiso 1.000000 R
C28 C 0.2648(3) 0.54016(13) 0.9074(3) 0.0496(8) Uani 1.000000 .
H28 H 0.3243(3) 0.52903(13) 0.8517(3) 0.0596(9) Uiso 1.000000 R
C25 C 0.0082(4) 0.65010(15) 0.4001(3) 0.0650(10) Uani 1.000000 .
H25a H -0.025(2) 0.6691(3) 0.3232(6) 0.0974(15) Uiso 1.000000 GR
H25b H 0.0756(8) 0.6179(5) 0.3905(16) 0.0974(15) Uiso 1.000000 GR
H25c H -0.0758(15) 0.6341(7) 0.4306(10) 0.0974(15) Uiso 1.000000 GR
C6 C 0.5091(3) 0.75368(13) 0.6261(3) 0.0495(8) Uani 1.000000 .
H6 H 0.5257(3) 0.78598(13) 0.5772(3) 0.0594(9) Uiso 1.000000 R
C29 C 0.2870(3) 0.51500(13) 1.0216(3) 0.0569(9) Uani 1.000000 .
H29 H 0.3626(3) 0.48667(13) 1.0419(3) 0.0683(11) Uiso 1.000000 R
C16 C -0.0726(4) 0.87860(15) 0.9298(3) 0.0587(9) Uani 1.000000 .
H16 H -0.1435(4) 0.86795(15) 0.9764(3) 0.0704(11) Uiso 1.000000 R
C18 C 0.1397(4) 0.93614(15) 0.9039(4) 0.0665(10) Uani 1.000000 .
H18 H 0.2117(4) 0.96482(15) 0.9328(4) 0.0798(12) Uiso 1.000000 R
C33 C 0.2283(4) 0.50258(15) 1.2315(3) 0.0769(12) Uani 1.000000 .
H33a H 0.190(2) 0.5288(5) 1.2869(6) 0.1154(18) Uiso 1.000000 GR
H33b H 0.179(2) 0.4642(5) 1.2289(6) 0.1154(18) Uiso 1.000000 GR
H33c H 0.3333(5) 0.4970(10) 1.2582(9) 0.1154(18) Uiso 1.000000 GR
C19 C 0.1380(3) 0.90981(13) 0.7908(3) 0.0533(8) Uani 1.000000 .
H19 H 0.2094(3) 0.92048(13) 0.7448(3) 0.0640(10) Uiso 1.000000 R
C17 C 0.0358(5) 0.91996(16) 0.9727(3) 0.0694(10) Uani 1.000000 .
H17 H 0.0389(5) 0.93711(16) 1.0487(3) 0.0833(12) Uiso 1.000000 R


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
S20 O22 1.430(2) . ?
S20 O21 1.4326(18) . ?
S20 N11 1.653(2) . ?
S20 C27 1.760(3) . ?
O24 C23 1.327(3) . ?
O24 C25 1.451(3) . ?
O26 C23 1.204(3) . ?
O2 N3 1.426(3) . ?
O2 C1 1.453(3) . ?
N11 C10 1.439(3) . ?
N11 C12 1.471(3) . ?
N3 C4 1.280(3) . ?
C23 C13 1.536(3) . ?
C10 C5 1.388(4) . ?
C10 C9 1.393(4) . ?
C5 C4 1.465(4) . ?
C5 C6 1.401(3) . ?
C4 C13 1.510(3) . ?
C32 C27 1.376(4) . ?
C32 C31 1.376(4) . ?
C27 C28 1.394(4) . ?
C9 C8 1.374(4) . ?
C1 C14 1.515(4) . ?
C1 C13 1.550(3) . ?
C12 C13 1.538(3) . ?
C14 C15 1.382(4) . ?
C14 C19 1.391(4) . ?
C30 C31 1.392(4) . ?
C30 C29 1.382(4) . ?
C30 C33 1.506(4) . ?
C8 C7 1.377(4) . ?
C7 C6 1.375(4) . ?
C15 C16 1.380(4) . ?
C28 C29 1.379(4) . ?
C16 C17 1.372(5) . ?
C18 C19 1.393(5) . ?
C18 C17 1.371(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
O21 S20 O22 120.55(13) . . ?
N11 S20 O22 108.07(11) . . ?
N11 S20 O21 105.65(11) . . ?
C27 S20 O22 107.97(13) . . ?
C27 S20 O21 107.62(12) . . ?
C27 S20 N11 106.13(12) . . ?
C25 O24 C23 116.4(2) . . ?
C1 O2 N3 108.55(19) . . ?
C10 N11 S20 121.11(16) . . ?
C12 N11 S20 120.12(16) . . ?
C12 N11 C10 115.85(19) . . ?
C4 N3 O2 108.3(2) . . ?
O26 C23 O24 124.7(2) . . ?
C13 C23 O24 111.8(2) . . ?
C13 C23 O26 123.5(3) . . ?
C5 C10 N11 119.7(2) . . ?
C9 C10 N11 120.4(2) . . ?
C9 C10 C5 119.8(2) . . ?
C4 C5 C10 119.0(2) . . ?
C6 C5 C10 119.0(2) . . ?
C6 C5 C4 122.0(3) . . ?
C5 C4 N3 124.2(2) . . ?
C13 C4 N3 113.9(2) . . ?
C13 C4 C5 121.3(2) . . ?
C31 C32 C27 120.1(3) . . ?
C32 C27 S20 120.0(2) . . ?
C28 C27 S20 120.1(2) . . ?
C28 C27 C32 119.9(3) . . ?
C8 C9 C10 119.8(3) . . ?
C14 C1 O2 111.7(2) . . ?
C13 C1 O2 102.4(2) . . ?
C13 C1 C14 115.2(2) . . ?
C13 C12 N11 110.3(2) . . ?
C15 C14 C1 119.7(2) . . ?
C19 C14 C1 121.4(3) . . ?
C19 C14 C15 118.9(3) . . ?
C4 C13 C23 111.9(2) . . ?
C1 C13 C23 109.6(2) . . ?
C1 C13 C4 99.3(2) . . ?
C12 C13 C23 109.9(2) . . ?
C12 C13 C4 107.4(2) . . ?
C12 C13 C1 118.3(2) . . ?
C29 C30 C31 117.3(3) . . ?
C33 C30 C31 121.2(3) . . ?
C33 C30 C29 121.5(3) . . ?
C30 C31 C32 121.4(3) . . ?
C7 C8 C9 121.2(3) . . ?
C6 C7 C8 119.3(3) . . ?
C16 C15 C14 121.1(3) . . ?
C29 C28 C27 118.8(3) . . ?
C7 C6 C5 120.9(3) . . ?
C28 C29 C30 122.4(3) . . ?
C17 C16 C15 119.7(3) . . ?
C17 C18 C19 120.3(3) . . ?
C18 C19 C14 119.7(3) . . ?
C18 C17 C16 120.3(3) . . ?

_olex2_date_sample_data_collection 2013-10-12
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1406080'
_audit_update_record             
;
2015-06-19 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'3-(2-chlorophenyl)-5-tosyl-3,3a,4,5-tetrahydroisoxazolo [4,3-c] quinoline - 3a- carbonitrile'
_chemical_name_common            
'3-(2-chlorophenyl)-5-tosyl-3,3a,4,5-tetrahydroisoxazolo [4,3-c] quinoline - 3a- carbonitrile'
_chemical_melting_point          435.15
_chemical_formula_moiety         'C24 H18 Cl N3 O3 S'
_chemical_formula_sum            'C24 H18 Cl N3 O3 S'
_chemical_formula_weight         463.92

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   9.398(2)
_cell_length_b                   9.776(2)
_cell_length_c                   24.059(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2210.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       strong
_exptl_crystal_colour            clourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    2.680
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            10416
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.67
_diffrn_reflns_theta_max         66.66
_reflns_number_total             3226
_reflns_number_gt                2703
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 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. 
;

_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)+(0.1427P)²+0.3352P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.41(3)
_refine_ls_number_reflns         3226
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1969
_refine_ls_wR_factor_gt          0.1529
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.74595(14) 0.73931(11) 0.58492(4) 0.0459(3) Uani 1 1 d . . .
Cl1 Cl 0.9725(2) 0.9313(2) 0.76633(7) 0.0876(6) Uani 1 1 d . . .
O1 O 0.6633(5) 0.8005(4) 0.54183(13) 0.0647(11) Uani 1 1 d . . .
O2 O 0.8691(4) 0.8094(4) 0.60425(14) 0.0589(9) Uani 1 1 d . . .
N1 N 0.6403(5) 0.7149(4) 0.63944(13) 0.0458(9) Uani 1 1 d . . .
O3 O 0.5152(5) 0.9105(4) 0.80644(15) 0.0708(11) Uani 1 1 d . . .
C6 C 0.4029(5) 0.7601(4) 0.67640(18) 0.0437(10) Uani 1 1 d . . .
N2 N 0.4134(5) 0.8551(5) 0.77000(18) 0.0591(12) Uani 1 1 d . . .
C19 C 0.7461(6) 0.4558(5) 0.58816(18) 0.0532(12) Uani 1 1 d . . .
H24 H 0.6840 0.4614 0.6182 0.064 Uiso 1 1 calc R . .
N3 N 0.6654(7) 1.0734(5) 0.6554(3) 0.0829(17) Uani 1 1 d . . .
C7 C 0.4702(6) 0.8293(5) 0.72311(18) 0.0449(10) Uani 1 1 d . . .
C18 C 0.7985(6) 0.5733(5) 0.56345(16) 0.0469(12) Uani 1 1 d . . .
C20 C 0.7875(7) 0.3303(6) 0.5676(2) 0.0615(15) Uani 1 1 d . . .
H25 H 0.7521 0.2510 0.5838 0.074 Uiso 1 1 calc R . .
C8 C 0.6291(6) 0.8632(4) 0.72024(17) 0.0439(10) Uani 1 1 d . . .
C23 C 0.8938(8) 0.5661(6) 0.5204(2) 0.0655(16) Uani 1 1 d . . .
H28 H 0.9308 0.6454 0.5047 0.079 Uiso 1 1 calc R . .
C21 C 0.8814(7) 0.3200(6) 0.5228(2) 0.0622(14) Uani 1 1 d . . .
C17 C 0.7003(5) 0.7349(5) 0.69513(16) 0.0423(10) Uani 1 1 d . . .
H00A H 0.8025 0.7477 0.6928 0.051 Uiso 1 1 calc R . .
H00B H 0.6813 0.6556 0.7182 0.051 Uiso 1 1 calc R . .
C5 C 0.2541(6) 0.7452(5) 0.6728(2) 0.0538(11) Uani 1 1 d . . .
H6 H 0.1968 0.7791 0.7012 0.065 Uiso 1 1 calc R . .
C1 C 0.4876(5) 0.7056(5) 0.63445(16) 0.0436(10) Uani 1 1 d . . .
C10 C 0.7467(7) 0.7981(5) 0.81252(17) 0.0539(12) Uani 1 1 d . . .
C16 C 0.6501(6) 0.9812(5) 0.6837(2) 0.0564(13) Uani 1 1 d . . .
C22 C 0.9334(8) 0.4404(7) 0.5009(2) 0.0755(19) Uani 1 1 d . . .
H27 H 0.9980 0.4358 0.4717 0.091 Uiso 1 1 calc R . .
C3 C 0.2778(6) 0.6272(6) 0.5868(2) 0.0606(14) Uani 1 1 d . . .
H4 H 0.2357 0.5825 0.5569 0.073 Uiso 1 1 calc R . .
C2 C 0.4259(6) 0.6384(6) 0.58940(18) 0.0523(12) Uani 1 1 d . . .
H3 H 0.4825 0.6016 0.5614 0.063 Uiso 1 1 calc R . .
C4 C 0.1929(6) 0.6819(7) 0.6284(2) 0.0602(14) Uani 1 1 d . . .
H5 H 0.0944 0.6754 0.6259 0.072 Uiso 1 1 calc R . .
C9 C 0.6570(6) 0.9001(6) 0.7825(2) 0.0554(12) Uani 1 1 d . . .
H10 H 0.7033 0.9898 0.7844 0.066 Uiso 1 1 calc R . .
C14 C 0.9829(11) 0.7056(9) 0.8305(3) 0.091(2) Uani 1 1 d . . .
H15 H 1.0810 0.7115 0.8260 0.109 Uiso 1 1 calc R . .
C11 C 0.6868(9) 0.6936(7) 0.8442(2) 0.0743(18) Uani 1 1 d . . .
H18 H 0.5888 0.6893 0.8493 0.089 Uiso 1 1 calc R . .
C15 C 0.8937(7) 0.8020(7) 0.8066(2) 0.0663(16) Uani 1 1 d . . .
C13 C 0.9242(14) 0.6019(10) 0.8607(3) 0.106(3) Uani 1 1 d . . .
H16 H 0.9829 0.5356 0.8763 0.128 Uiso 1 1 calc R . .
C12 C 0.7768(15) 0.5938(8) 0.8686(3) 0.106(4) Uani 1 1 d . . .
H17 H 0.7381 0.5234 0.8897 0.127 Uiso 1 1 calc R . .
C24 C 0.9229(12) 0.1806(8) 0.5001(3) 0.101(3) Uani 1 1 d . . .
H29A H 0.9045 0.1778 0.4609 0.151 Uiso 1 1 calc R . .
H29B H 0.8681 0.1110 0.5184 0.151 Uiso 1 1 calc R . .
H29C H 1.0223 0.1649 0.5067 0.151 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 O2 1.423(4) . ?
S1 O1 1.427(4) . ?
S1 N1 1.662(4) . ?
S1 C18 1.773(5) . ?
Cl1 C15 1.757(7) . ?
N1 C1 1.444(6) . ?
N1 C17 1.466(5) . ?
O3 N2 1.407(6) . ?
O3 C9 1.455(7) . ?
C6 C1 1.391(6) . ?
C6 C5 1.409(7) . ?
C6 C7 1.456(7) . ?
N2 C7 1.273(6) . ?
C19 C20 1.378(8) . ?
C19 C18 1.384(7) . ?
C19 H24 0.9300 . ?
N3 C16 1.139(7) . ?
C7 C8 1.532(7) . ?
C18 C23 1.372(7) . ?
C20 C21 1.396(8) . ?
C20 H25 0.9300 . ?
C8 C16 1.463(7) . ?
C8 C17 1.545(6) . ?
C8 C9 1.562(6) . ?
C23 C22 1.367(9) . ?
C23 H28 0.9300 . ?
C21 C22 1.379(9) . ?
C21 C24 1.519(8) . ?
C17 H00A 0.9700 . ?
C17 H00B 0.9700 . ?
C5 C4 1.363(8) . ?
C5 H6 0.9300 . ?
C1 C2 1.393(7) . ?
C10 C15 1.390(9) . ?
C10 C11 1.394(9) . ?
C10 C9 1.492(8) . ?
C22 H27 0.9300 . ?
C3 C4 1.386(8) . ?
C3 C2 1.398(8) . ?
C3 H4 0.9300 . ?
C2 H3 0.9300 . ?
C4 H5 0.9300 . ?
C9 H10 0.9800 . ?
C14 C13 1.364(14) . ?
C14 C15 1.386(10) . ?
C14 H15 0.9300 . ?
C11 C12 1.418(12) . ?
C11 H18 0.9300 . ?
C13 C12 1.400(14) . ?
C13 H16 0.9300 . ?
C12 H17 0.9300 . ?
C24 H29A 0.9600 . ?
C24 H29B 0.9600 . ?
C24 H29C 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 118.6(3) . . ?
O2 S1 N1 107.3(2) . . ?
O1 S1 N1 108.0(2) . . ?
O2 S1 C18 108.0(2) . . ?
O1 S1 C18 108.9(2) . . ?
N1 S1 C18 105.4(2) . . ?
C1 N1 C17 117.8(3) . . ?
C1 N1 S1 122.5(3) . . ?
C17 N1 S1 118.2(3) . . ?
N2 O3 C9 110.4(3) . . ?
C1 C6 C5 118.9(4) . . ?
C1 C6 C7 119.3(4) . . ?
C5 C6 C7 121.7(4) . . ?
C7 N2 O3 110.0(5) . . ?
C20 C19 C18 119.0(4) . . ?
C20 C19 H24 120.5 . . ?
C18 C19 H24 120.5 . . ?
N2 C7 C6 126.4(5) . . ?
N2 C7 C8 114.0(4) . . ?
C6 C7 C8 119.3(4) . . ?
C23 C18 C19 120.9(5) . . ?
C23 C18 S1 116.7(4) . . ?
C19 C18 S1 122.4(4) . . ?
C19 C20 C21 121.3(5) . . ?
C19 C20 H25 119.3 . . ?
C21 C20 H25 119.3 . . ?
C16 C8 C7 109.2(4) . . ?
C16 C8 C17 110.3(4) . . ?
C7 C8 C17 105.3(4) . . ?
C16 C8 C9 111.8(4) . . ?
C7 C8 C9 99.8(4) . . ?
C17 C8 C9 119.3(4) . . ?
C18 C23 C22 118.9(5) . . ?
C18 C23 H28 120.6 . . ?
C22 C23 H28 120.6 . . ?
C22 C21 C20 117.2(5) . . ?
C22 C21 C24 122.5(5) . . ?
C20 C21 C24 120.3(6) . . ?
N1 C17 C8 107.4(4) . . ?
N1 C17 H00A 110.2 . . ?
C8 C17 H00A 110.2 . . ?
N1 C17 H00B 110.2 . . ?
C8 C17 H00B 110.2 . . ?
H00A C17 H00B 108.5 . . ?
C4 C5 C6 120.9(5) . . ?
C4 C5 H6 119.5 . . ?
C6 C5 H6 119.5 . . ?
C6 C1 C2 120.5(5) . . ?
C6 C1 N1 118.9(4) . . ?
C2 C1 N1 120.5(4) . . ?
C15 C10 C11 118.5(6) . . ?
C15 C10 C9 119.6(5) . . ?
C11 C10 C9 121.8(6) . . ?
N3 C16 C8 179.5(7) . . ?
C23 C22 C21 122.6(5) . . ?
C23 C22 H27 118.7 . . ?
C21 C22 H27 118.7 . . ?
C4 C3 C2 120.7(5) . . ?
C4 C3 H4 119.6 . . ?
C2 C3 H4 119.6 . . ?
C3 C2 C1 119.1(5) . . ?
C3 C2 H3 120.5 . . ?
C1 C2 H3 120.5 . . ?
C5 C4 C3 119.9(5) . . ?
C5 C4 H5 120.1 . . ?
C3 C4 H5 120.1 . . ?
O3 C9 C10 111.8(5) . . ?
O3 C9 C8 104.0(4) . . ?
C10 C9 C8 113.9(4) . . ?
O3 C9 H10 109.0 . . ?
C10 C9 H10 109.0 . . ?
C8 C9 H10 109.0 . . ?
C13 C14 C15 118.8(9) . . ?
C13 C14 H15 120.6 . . ?
C15 C14 H15 120.6 . . ?
C10 C11 C12 119.4(9) . . ?
C10 C11 H18 120.3 . . ?
C12 C11 H18 120.3 . . ?
C14 C15 C10 122.7(7) . . ?
C14 C15 Cl1 117.6(7) . . ?
C10 C15 Cl1 119.7(5) . . ?
C14 C13 C12 121.0(8) . . ?
C14 C13 H16 119.5 . . ?
C12 C13 H16 119.5 . . ?
C13 C12 C11 119.7(9) . . ?
C13 C12 H17 120.2 . . ?
C11 C12 H17 120.2 . . ?
C21 C24 H29A 109.5 . . ?
C21 C24 H29B 109.5 . . ?
H29A C24 H29B 109.5 . . ?
C21 C24 H29C 109.5 . . ?
H29A C24 H29C 109.5 . . ?
H29B C24 H29C 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 N1 C1 151.4(4) . . . . ?
O1 S1 N1 C1 22.5(4) . . . . ?
C18 S1 N1 C1 -93.7(4) . . . . ?
O2 S1 N1 C17 -14.4(4) . . . . ?
O1 S1 N1 C17 -143.2(4) . . . . ?
C18 S1 N1 C17 100.6(4) . . . . ?
C9 O3 N2 C7 -9.4(6) . . . . ?
O3 N2 C7 C6 174.0(4) . . . . ?
O3 N2 C7 C8 0.8(6) . . . . ?
C1 C6 C7 N2 -162.1(5) . . . . ?
C5 C6 C7 N2 17.1(7) . . . . ?
C1 C6 C7 C8 10.8(6) . . . . ?
C5 C6 C7 C8 -170.0(4) . . . . ?
C20 C19 C18 C23 -2.2(8) . . . . ?
C20 C19 C18 S1 177.3(4) . . . . ?
O2 S1 C18 C23 -62.0(5) . . . . ?
O1 S1 C18 C23 68.0(5) . . . . ?
N1 S1 C18 C23 -176.4(4) . . . . ?
O2 S1 C18 C19 118.5(4) . . . . ?
O1 S1 C18 C19 -111.5(4) . . . . ?
N1 S1 C18 C19 4.1(5) . . . . ?
C18 C19 C20 C21 0.5(9) . . . . ?
N2 C7 C8 C16 -110.3(5) . . . . ?
C6 C7 C8 C16 75.9(5) . . . . ?
N2 C7 C8 C17 131.3(4) . . . . ?
C6 C7 C8 C17 -42.5(5) . . . . ?
N2 C7 C8 C9 7.1(5) . . . . ?
C6 C7 C8 C9 -166.7(4) . . . . ?
C19 C18 C23 C22 2.0(10) . . . . ?
S1 C18 C23 C22 -177.5(5) . . . . ?
C19 C20 C21 C22 1.3(9) . . . . ?
C19 C20 C21 C24 -178.7(6) . . . . ?
C1 N1 C17 C8 -54.9(5) . . . . ?
S1 N1 C17 C8 111.6(4) . . . . ?
C16 C8 C17 N1 -56.3(5) . . . . ?
C7 C8 C17 N1 61.4(4) . . . . ?
C9 C8 C17 N1 172.2(4) . . . . ?
C1 C6 C5 C4 -1.8(7) . . . . ?
C7 C6 C5 C4 179.0(5) . . . . ?
C5 C6 C1 C2 0.5(6) . . . . ?
C7 C6 C1 C2 179.8(4) . . . . ?
C5 C6 C1 N1 -177.0(4) . . . . ?
C7 C6 C1 N1 2.2(6) . . . . ?
C17 N1 C1 C6 21.6(6) . . . . ?
S1 N1 C1 C6 -144.3(3) . . . . ?
C17 N1 C1 C2 -156.0(4) . . . . ?
S1 N1 C1 C2 38.2(6) . . . . ?
C7 C8 C16 N3 31(80) . . . . ?
C17 C8 C16 N3 146(80) . . . . ?
C9 C8 C16 N3 -78(80) . . . . ?
C18 C23 C22 C21 0.0(11) . . . . ?
C20 C21 C22 C23 -1.6(11) . . . . ?
C24 C21 C22 C23 178.4(8) . . . . ?
C4 C3 C2 C1 0.0(8) . . . . ?
C6 C1 C2 C3 0.3(7) . . . . ?
N1 C1 C2 C3 177.8(4) . . . . ?
C6 C5 C4 C3 2.1(8) . . . . ?
C2 C3 C4 C5 -1.2(9) . . . . ?
N2 O3 C9 C10 -110.1(4) . . . . ?
N2 O3 C9 C8 13.3(5) . . . . ?
C15 C10 C9 O3 -161.5(4) . . . . ?
C11 C10 C9 O3 22.1(6) . . . . ?
C15 C10 C9 C8 80.9(6) . . . . ?
C11 C10 C9 C8 -95.5(5) . . . . ?
C16 C8 C9 O3 103.9(5) . . . . ?
C7 C8 C9 O3 -11.5(5) . . . . ?
C17 C8 C9 O3 -125.4(5) . . . . ?
C16 C8 C9 C10 -134.1(5) . . . . ?
C7 C8 C9 C10 110.5(5) . . . . ?
C17 C8 C9 C10 -3.3(7) . . . . ?
C15 C10 C11 C12 -0.9(7) . . . . ?
C9 C10 C11 C12 175.5(5) . . . . ?
C13 C14 C15 C10 0.5(9) . . . . ?
C13 C14 C15 Cl1 -178.2(5) . . . . ?
C11 C10 C15 C14 0.6(7) . . . . ?
C9 C10 C15 C14 -176.0(5) . . . . ?
C11 C10 C15 Cl1 179.3(4) . . . . ?
C9 C10 C15 Cl1 2.8(6) . . . . ?
C15 C14 C13 C12 -1.3(11) . . . . ?
C14 C13 C12 C11 0.9(11) . . . . ?
C10 C11 C12 C13 0.2(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.877
_diffrn_reflns_theta_full        66.66
_diffrn_measured_fraction_theta_full 0.877
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.148
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethonal'
_chemical_compound_source        synthatic
