# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013


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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_a
_database_code_depnum_ccdc_archive 'CCDC 847690'
#TrackingRef '101130a_0m.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 N2 O4 S'
_chemical_formula_weight         406.44
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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
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'
'-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                   10.427(2)
_cell_length_b                   19.086(4)
_cell_length_c                   19.748(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3929.9(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.49
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9730
_exptl_absorpt_correction_T_max  0.9787
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32048
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         27.53
_reflns_number_total             4512
_reflns_number_gt                3521
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0506P)^2^+1.4066P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4512
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 1.09085(5) 0.23122(2) 0.62425(3) 0.06232(16) Uani 1 1 d . . .
O1 O 0.51884(18) 0.41797(9) 0.75305(9) 0.0955(5) Uani 1 1 d . . .
O2 O 0.39718(14) 0.40608(8) 0.66644(9) 0.0833(5) Uani 1 1 d . . .
O3 O 0.85367(14) 0.19897(8) 0.51654(6) 0.0700(4) Uani 1 1 d . . .
O4 O 0.56947(13) -0.08351(8) 0.56899(8) 0.0731(4) Uani 1 1 d . . .
N1 N 1.08759(13) 0.06909(7) 0.63890(7) 0.0503(3) Uani 1 1 d . . .
H1 H 1.0701 0.0300 0.6585 0.060 Uiso 1 1 calc R . .
N2 N 0.49489(16) 0.39311(8) 0.69801(9) 0.0615(4) Uani 1 1 d . . .
C1 C 1.20327(15) 0.10178(8) 0.65214(8) 0.0443(3) Uani 1 1 d . . .
C2 C 1.30927(16) 0.06271(10) 0.67269(9) 0.0527(4) Uani 1 1 d . . .
H2 H 1.3016 0.0144 0.6773 0.063 Uiso 1 1 calc R . .
C3 C 1.42533(17) 0.09437(11) 0.68635(10) 0.0618(5) Uani 1 1 d . . .
H3 H 1.4947 0.0674 0.7005 0.074 Uiso 1 1 calc R . .
C4 C 1.43877(18) 0.16604(12) 0.67911(10) 0.0653(5) Uani 1 1 d . . .
H4 H 1.5174 0.1873 0.6875 0.078 Uiso 1 1 calc R . .
C5 C 1.33537(17) 0.20549(10) 0.65950(10) 0.0576(4) Uani 1 1 d . . .
H5 H 1.3444 0.2537 0.6548 0.069 Uiso 1 1 calc R . .
C6 C 1.21702(15) 0.17437(9) 0.64652(8) 0.0465(4) Uani 1 1 d . . .
C7 C 0.95532(16) 0.17118(9) 0.62104(8) 0.0473(4) Uani 1 1 d . . .
H7 H 0.9205 0.1650 0.6667 0.057 Uiso 1 1 calc R . .
C8 C 0.85683(16) 0.20832(9) 0.57707(8) 0.0482(4) Uani 1 1 d . . .
C9 C 0.76422(15) 0.25721(8) 0.61024(8) 0.0428(3) Uani 1 1 d . . .
C10 C 0.77783(16) 0.27847(9) 0.67704(8) 0.0519(4) Uani 1 1 d . . .
H10 H 0.8465 0.2621 0.7025 0.062 Uiso 1 1 calc R . .
C11 C 0.69058(17) 0.32368(9) 0.70598(9) 0.0537(4) Uani 1 1 d . . .
H11 H 0.7001 0.3387 0.7505 0.064 Uiso 1 1 calc R . .
C12 C 0.58937(15) 0.34582(8) 0.66716(9) 0.0467(4) Uani 1 1 d . . .
C13 C 0.57221(16) 0.32598(9) 0.60100(9) 0.0502(4) Uani 1 1 d . . .
H13 H 0.5023 0.3419 0.5762 0.060 Uiso 1 1 calc R . .
C14 C 0.66147(16) 0.28175(9) 0.57232(8) 0.0484(4) Uani 1 1 d . . .
H14 H 0.6528 0.2683 0.5273 0.058 Uiso 1 1 calc R . .
C15 C 0.99512(15) 0.09957(8) 0.59254(8) 0.0449(4) Uani 1 1 d . . .
H15 H 1.0356 0.1062 0.5482 0.054 Uiso 1 1 calc R . .
C16 C 0.88111(15) 0.05117(9) 0.58506(8) 0.0451(4) Uani 1 1 d . . .
C17 C 0.81279(17) 0.02792(10) 0.64108(9) 0.0516(4) Uani 1 1 d . . .
H17 H 0.8372 0.0426 0.6841 0.062 Uiso 1 1 calc R . .
C18 C 0.70928(17) -0.01650(10) 0.63405(9) 0.0547(4) Uani 1 1 d . . .
H18 H 0.6642 -0.0311 0.6722 0.066 Uiso 1 1 calc R . .
C19 C 0.67243(16) -0.03928(9) 0.57087(9) 0.0519(4) Uani 1 1 d . . .
C20 C 0.73914(18) -0.01678(10) 0.51438(9) 0.0569(4) Uani 1 1 d . . .
H20 H 0.7150 -0.0318 0.4714 0.068 Uiso 1 1 calc R . .
C21 C 0.84173(17) 0.02811(10) 0.52211(9) 0.0525(4) Uani 1 1 d . . .
H21 H 0.8857 0.0433 0.4838 0.063 Uiso 1 1 calc R . .
C22 C 0.5316(2) -0.11129(13) 0.50514(13) 0.0815(7) Uani 1 1 d . . .
H22A H 0.5111 -0.0735 0.4749 0.122 Uiso 1 1 calc R . .
H22B H 0.4575 -0.1406 0.5110 0.122 Uiso 1 1 calc R . .
H22C H 0.6005 -0.1385 0.4865 0.122 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0604(3) 0.0420(2) 0.0846(4) -0.0026(2) -0.0100(2) 0.00301(19)
O1 0.1029(13) 0.1020(12) 0.0817(11) -0.0262(10) 0.0179(10) 0.0357(10)
O2 0.0600(8) 0.0687(9) 0.1213(13) -0.0039(9) 0.0028(9) 0.0236(7)
O3 0.0848(10) 0.0832(10) 0.0420(7) -0.0041(6) 0.0039(6) 0.0311(8)
O4 0.0613(8) 0.0777(10) 0.0803(10) -0.0001(8) 0.0027(7) -0.0206(7)
N1 0.0469(7) 0.0423(7) 0.0616(9) 0.0066(6) -0.0018(6) 0.0000(6)
N2 0.0604(9) 0.0461(8) 0.0779(11) 0.0012(8) 0.0172(8) 0.0098(7)
C1 0.0445(8) 0.0487(9) 0.0398(8) 0.0002(6) 0.0050(6) 0.0018(7)
C2 0.0533(9) 0.0535(10) 0.0513(9) 0.0067(7) 0.0006(8) 0.0045(8)
C3 0.0479(9) 0.0758(13) 0.0618(11) 0.0048(9) -0.0024(8) 0.0063(9)
C4 0.0484(9) 0.0758(13) 0.0717(12) -0.0024(10) 0.0005(9) -0.0089(9)
C5 0.0537(10) 0.0558(10) 0.0634(11) -0.0021(8) 0.0056(8) -0.0076(8)
C6 0.0479(8) 0.0473(9) 0.0442(8) -0.0025(7) 0.0045(7) 0.0014(7)
C7 0.0491(8) 0.0467(9) 0.0461(8) -0.0020(7) 0.0028(7) 0.0068(7)
C8 0.0513(9) 0.0492(9) 0.0440(9) -0.0006(7) 0.0043(7) 0.0061(7)
C9 0.0449(8) 0.0415(8) 0.0418(8) 0.0010(6) 0.0028(6) 0.0018(6)
C10 0.0498(9) 0.0599(10) 0.0460(9) -0.0052(7) -0.0048(7) 0.0115(8)
C11 0.0584(10) 0.0564(10) 0.0463(9) -0.0081(7) 0.0013(8) 0.0068(8)
C12 0.0447(8) 0.0377(8) 0.0577(10) 0.0015(7) 0.0106(7) 0.0027(6)
C13 0.0458(8) 0.0473(9) 0.0576(10) 0.0054(8) -0.0045(7) 0.0044(7)
C14 0.0508(9) 0.0504(9) 0.0440(8) -0.0003(7) -0.0030(7) 0.0019(7)
C15 0.0455(8) 0.0449(8) 0.0444(8) -0.0020(7) 0.0051(7) 0.0043(6)
C16 0.0428(8) 0.0457(8) 0.0468(9) -0.0017(7) 0.0046(7) 0.0057(6)
C17 0.0528(9) 0.0584(10) 0.0437(9) -0.0010(7) 0.0034(7) 0.0023(8)
C18 0.0514(9) 0.0594(10) 0.0532(10) 0.0050(8) 0.0118(8) 0.0011(8)
C19 0.0424(8) 0.0511(9) 0.0621(11) -0.0006(8) 0.0030(8) 0.0011(7)
C20 0.0567(10) 0.0644(11) 0.0496(10) -0.0085(8) 0.0017(8) -0.0025(9)
C21 0.0521(9) 0.0600(10) 0.0455(9) -0.0039(7) 0.0103(7) -0.0017(8)
C22 0.0757(14) 0.0712(14) 0.0976(17) -0.0043(12) -0.0173(13) -0.0179(11)
_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 C6 1.7610(17) . ?
S1 C7 1.8205(18) . ?
O1 N2 1.212(2) . ?
O2 N2 1.220(2) . ?
O3 C8 1.209(2) . ?
O4 C19 1.366(2) . ?
O4 C22 1.424(3) . ?
N1 C1 1.383(2) . ?
N1 C15 1.451(2) . ?
N1 H1 0.8600 . ?
N2 C12 1.469(2) . ?
C1 C2 1.394(2) . ?
C1 C6 1.397(2) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9300 . ?
C7 C8 1.520(2) . ?
C7 C15 1.535(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.494(2) . ?
C9 C10 1.387(2) . ?
C9 C14 1.389(2) . ?
C10 C11 1.378(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(2) . ?
C13 C14 1.378(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.513(2) . ?
C15 H15 0.9800 . ?
C16 C21 1.381(2) . ?
C16 C17 1.389(2) . ?
C17 C18 1.379(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(2) . ?
C20 C21 1.379(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C6 S1 C7 101.58(8) . . ?
C19 O4 C22 118.18(16) . . ?
C1 N1 C15 121.19(13) . . ?
C1 N1 H1 119.4 . . ?
C15 N1 H1 119.4 . . ?
O1 N2 O2 123.45(17) . . ?
O1 N2 C12 118.33(17) . . ?
O2 N2 C12 118.22(17) . . ?
N1 C1 C2 120.35(15) . . ?
N1 C1 C6 121.45(14) . . ?
C2 C1 C6 118.19(15) . . ?
C3 C2 C1 121.22(17) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 120.14(18) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.54(18) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.95(18) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.93(16) . . ?
C5 C6 S1 116.42(13) . . ?
C1 C6 S1 123.65(13) . . ?
C8 C7 C15 112.85(13) . . ?
C8 C7 S1 104.52(11) . . ?
C15 C7 S1 111.30(11) . . ?
C8 C7 H7 109.3 . . ?
C15 C7 H7 109.3 . . ?
S1 C7 H7 109.3 . . ?
O3 C8 C9 120.54(15) . . ?
O3 C8 C7 120.95(15) . . ?
C9 C8 C7 118.51(14) . . ?
C10 C9 C14 119.55(15) . . ?
C10 C9 C8 122.24(14) . . ?
C14 C9 C8 118.22(14) . . ?
C11 C10 C9 120.66(16) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 117.98(16) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C11 C12 C13 123.22(15) . . ?
C11 C12 N2 118.28(16) . . ?
C13 C12 N2 118.51(15) . . ?
C12 C13 C14 118.18(15) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
C13 C14 C9 120.39(16) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
N1 C15 C16 109.81(13) . . ?
N1 C15 C7 107.78(13) . . ?
C16 C15 C7 111.53(13) . . ?
N1 C15 H15 109.2 . . ?
C16 C15 H15 109.2 . . ?
C7 C15 H15 109.2 . . ?
C21 C16 C17 117.56(16) . . ?
C21 C16 C15 121.07(14) . . ?
C17 C16 C15 121.36(15) . . ?
C18 C17 C16 121.17(16) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 120.26(16) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
O4 C19 C18 116.06(16) . . ?
O4 C19 C20 124.42(17) . . ?
C18 C19 C20 119.53(16) . . ?
C21 C20 C19 119.58(16) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C16 121.89(16) . . ?
C20 C21 H21 119.1 . . ?
C16 C21 H21 119.1 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C15 N1 C1 C2 -153.98(15) . . . . ?
C15 N1 C1 C6 27.1(2) . . . . ?
N1 C1 C2 C3 -179.78(16) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C4 C5 C6 S1 178.11(15) . . . . ?
N1 C1 C6 C5 -179.27(15) . . . . ?
C2 C1 C6 C5 1.8(2) . . . . ?
N1 C1 C6 S1 1.4(2) . . . . ?
C2 C1 C6 S1 -177.57(12) . . . . ?
C7 S1 C6 C5 -174.25(13) . . . . ?
C7 S1 C6 C1 5.11(16) . . . . ?
C6 S1 C7 C8 -158.80(11) . . . . ?
C6 S1 C7 C15 -36.69(13) . . . . ?
C15 C7 C8 O3 -29.7(2) . . . . ?
S1 C7 C8 O3 91.35(18) . . . . ?
C15 C7 C8 C9 150.69(14) . . . . ?
S1 C7 C8 C9 -88.22(15) . . . . ?
O3 C8 C9 C10 -168.92(18) . . . . ?
C7 C8 C9 C10 10.7(2) . . . . ?
O3 C8 C9 C14 11.1(2) . . . . ?
C7 C8 C9 C14 -169.32(15) . . . . ?
C14 C9 C10 C11 -0.1(3) . . . . ?
C8 C9 C10 C11 179.96(16) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
C10 C11 C12 C13 -1.0(3) . . . . ?
C10 C11 C12 N2 179.04(16) . . . . ?
O1 N2 C12 C11 9.7(2) . . . . ?
O2 N2 C12 C11 -171.35(17) . . . . ?
O1 N2 C12 C13 -170.30(18) . . . . ?
O2 N2 C12 C13 8.7(2) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
N2 C12 C13 C14 179.81(15) . . . . ?
C12 C13 C14 C9 1.2(2) . . . . ?
C10 C9 C14 C13 -1.1(2) . . . . ?
C8 C9 C14 C13 178.86(15) . . . . ?
C1 N1 C15 C16 177.19(14) . . . . ?
C1 N1 C15 C7 -61.13(18) . . . . ?
C8 C7 C15 N1 -179.37(13) . . . . ?
S1 C7 C15 N1 63.47(15) . . . . ?
C8 C7 C15 C16 -58.77(18) . . . . ?
S1 C7 C15 C16 -175.92(11) . . . . ?
N1 C15 C16 C21 -125.04(17) . . . . ?
C7 C15 C16 C21 115.56(17) . . . . ?
N1 C15 C16 C17 54.5(2) . . . . ?
C7 C15 C16 C17 -64.9(2) . . . . ?
C21 C16 C17 C18 -0.1(3) . . . . ?
C15 C16 C17 C18 -179.67(15) . . . . ?
C16 C17 C18 C19 0.7(3) . . . . ?
C22 O4 C19 C18 -176.94(18) . . . . ?
C22 O4 C19 C20 3.3(3) . . . . ?
C17 C18 C19 O4 179.56(16) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
O4 C19 C20 C21 179.86(17) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C19 C20 C21 C16 0.5(3) . . . . ?
C17 C16 C21 C20 -0.5(3) . . . . ?
C15 C16 C21 C20 179.09(16) . . . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.036


data_a
_database_code_depnum_ccdc_archive 'CCDC 847691'
#TrackingRef '101130b_0m.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 Cl2 N O S'
_chemical_formula_weight         414.33
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   10.1879(10)
_cell_length_b                   10.7179(10)
_cell_length_c                   11.0530(11)
_cell_angle_alpha                95.3630(10)
_cell_angle_beta                 109.8910(10)
_cell_angle_gamma                115.9520(10)
_cell_volume                     977.64(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4984
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.451
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9396
_exptl_absorpt_correction_T_max  0.9521
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7592
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3797
_reflns_number_gt                3255
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0490P)^2^+0.3262P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3797
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
Cl1 Cl 0.45658(8) 0.37770(7) -0.14149(7) 0.0789(2) Uani 1 1 d . . .
Cl2 Cl 0.11420(8) -0.07074(8) -0.58763(7) 0.0937(2) Uani 1 1 d . . .
S1 S 0.71387(6) 0.10675(5) 0.08208(5) 0.05645(16) Uani 1 1 d . . .
O1 O 0.94864(17) 0.47957(16) 0.18141(15) 0.0666(4) Uani 1 1 d . . .
N1 N 0.85520(19) 0.2868(2) -0.08610(17) 0.0596(4) Uani 1 1 d . . .
H1 H 0.8786 0.3136 -0.1505 0.072 Uiso 1 1 calc R . .
C1 C 0.9490(2) 0.24038(19) -0.00444(19) 0.0500(4) Uani 1 1 d . . .
C2 C 1.0961(2) 0.2713(2) -0.0080(2) 0.0586(5) Uani 1 1 d . . .
H2 H 1.1306 0.3262 -0.0627 0.070 Uiso 1 1 calc R . .
C3 C 1.1897(3) 0.2217(3) 0.0681(3) 0.0715(6) Uani 1 1 d . . .
H3 H 1.2861 0.2420 0.0632 0.086 Uiso 1 1 calc R . .
C4 C 1.1428(3) 0.1421(3) 0.1515(3) 0.0745(7) Uani 1 1 d . . .
H4 H 1.2064 0.1081 0.2023 0.089 Uiso 1 1 calc R . .
C5 C 1.0011(3) 0.1134(2) 0.1591(2) 0.0639(5) Uani 1 1 d . . .
H5 H 0.9707 0.0625 0.2175 0.077 Uiso 1 1 calc R . .
C6 C 0.9026(2) 0.15950(19) 0.08049(19) 0.0518(4) Uani 1 1 d . . .
C7 C 0.6989(2) 0.2648(2) 0.05139(18) 0.0483(4) Uani 1 1 d . . .
H7 H 0.5901 0.2441 0.0366 0.058 Uiso 1 1 calc R . .
C8 C 0.8174(2) 0.3939(2) 0.17503(19) 0.0499(4) Uani 1 1 d . . .
C9 C 0.7723(2) 0.41498(19) 0.28623(18) 0.0480(4) Uani 1 1 d . . .
C10 C 0.8761(2) 0.5423(2) 0.3912(2) 0.0598(5) Uani 1 1 d . . .
H10 H 0.9699 0.6116 0.3886 0.072 Uiso 1 1 calc R . .
C11 C 0.8431(3) 0.5682(2) 0.4989(2) 0.0645(5) Uani 1 1 d . . .
H11 H 0.9142 0.6545 0.5675 0.077 Uiso 1 1 calc R . .
C12 C 0.7047(3) 0.4665(2) 0.5058(2) 0.0578(5) Uani 1 1 d . . .
C13 C 0.6007(3) 0.3414(2) 0.4006(2) 0.0600(5) Uani 1 1 d . . .
H13 H 0.5066 0.2728 0.4030 0.072 Uiso 1 1 calc R . .
C14 C 0.6317(2) 0.3149(2) 0.2919(2) 0.0545(5) Uani 1 1 d . . .
H14 H 0.5584 0.2298 0.2221 0.065 Uiso 1 1 calc R . .
C15 C 0.6725(3) 0.4912(3) 0.6268(2) 0.0802(7) Uani 1 1 d . . .
H15A H 0.7391 0.4729 0.6997 0.120 Uiso 1 1 calc R . .
H15B H 0.5610 0.4267 0.6050 0.120 Uiso 1 1 calc R . .
H15C H 0.6970 0.5896 0.6526 0.120 Uiso 1 1 calc R . .
C16 C 0.7212(2) 0.2954(2) -0.07575(18) 0.0488(4) Uani 1 1 d . . .
H16 H 0.7452 0.3954 -0.0704 0.059 Uiso 1 1 calc R . .
C17 C 0.5649(2) 0.19937(19) -0.20023(18) 0.0464(4) Uani 1 1 d . . .
C18 C 0.4398(2) 0.2290(2) -0.2389(2) 0.0521(4) Uani 1 1 d . . .
C19 C 0.3008(2) 0.1480(2) -0.3567(2) 0.0609(5) Uani 1 1 d . . .
H19 H 0.2203 0.1725 -0.3818 0.073 Uiso 1 1 calc R . .
C20 C 0.2843(2) 0.0307(2) -0.4357(2) 0.0597(5) Uani 1 1 d . . .
C21 C 0.4022(3) -0.0062(2) -0.3994(2) 0.0615(5) Uani 1 1 d . . .
H21 H 0.3884 -0.0875 -0.4525 0.074 Uiso 1 1 calc R . .
C22 C 0.5410(2) 0.0783(2) -0.2835(2) 0.0557(5) Uani 1 1 d . . .
H22 H 0.6215 0.0537 -0.2600 0.067 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0779(4) 0.0779(4) 0.0894(4) 0.0077(3) 0.0319(3) 0.0519(3)
Cl2 0.0753(4) 0.0783(4) 0.0768(4) 0.0099(3) 0.0019(3) 0.0229(3)
S1 0.0542(3) 0.0525(3) 0.0665(3) 0.0279(2) 0.0314(2) 0.0234(2)
O1 0.0524(8) 0.0675(9) 0.0661(9) 0.0213(7) 0.0313(7) 0.0139(7)
N1 0.0505(9) 0.0838(12) 0.0617(10) 0.0386(9) 0.0341(8) 0.0364(9)
C1 0.0429(9) 0.0475(9) 0.0537(10) 0.0105(8) 0.0192(8) 0.0197(8)
C2 0.0484(10) 0.0530(11) 0.0699(12) 0.0106(9) 0.0268(10) 0.0220(9)
C3 0.0507(11) 0.0652(13) 0.0918(17) 0.0086(12) 0.0244(12) 0.0307(10)
C4 0.0649(13) 0.0663(14) 0.0867(16) 0.0171(12) 0.0164(12) 0.0411(12)
C5 0.0656(13) 0.0523(11) 0.0689(13) 0.0190(10) 0.0205(10) 0.0314(10)
C6 0.0486(10) 0.0459(9) 0.0567(10) 0.0135(8) 0.0204(8) 0.0222(8)
C7 0.0453(9) 0.0539(10) 0.0533(10) 0.0234(8) 0.0271(8) 0.0247(8)
C8 0.0483(10) 0.0520(10) 0.0548(10) 0.0259(8) 0.0254(8) 0.0248(8)
C9 0.0482(10) 0.0483(9) 0.0525(10) 0.0209(8) 0.0235(8) 0.0255(8)
C10 0.0546(11) 0.0533(11) 0.0668(12) 0.0194(9) 0.0275(10) 0.0216(9)
C11 0.0656(13) 0.0568(11) 0.0611(12) 0.0092(9) 0.0237(10) 0.0267(10)
C12 0.0669(12) 0.0647(12) 0.0586(11) 0.0239(10) 0.0316(10) 0.0416(11)
C13 0.0588(11) 0.0599(12) 0.0708(13) 0.0234(10) 0.0385(10) 0.0283(10)
C14 0.0522(10) 0.0517(10) 0.0598(11) 0.0169(9) 0.0288(9) 0.0223(9)
C15 0.0921(18) 0.0924(18) 0.0696(14) 0.0204(13) 0.0446(14) 0.0502(15)
C16 0.0468(9) 0.0540(10) 0.0532(10) 0.0228(8) 0.0262(8) 0.0263(8)
C17 0.0485(9) 0.0502(9) 0.0512(10) 0.0231(8) 0.0274(8) 0.0269(8)
C18 0.0513(10) 0.0523(10) 0.0600(11) 0.0179(9) 0.0270(9) 0.0291(9)
C19 0.0511(11) 0.0631(12) 0.0703(13) 0.0235(10) 0.0242(10) 0.0306(10)
C20 0.0546(11) 0.0563(11) 0.0573(11) 0.0209(9) 0.0198(9) 0.0211(9)
C21 0.0725(13) 0.0547(11) 0.0599(12) 0.0160(9) 0.0315(11) 0.0316(10)
C22 0.0616(12) 0.0612(11) 0.0613(11) 0.0256(9) 0.0318(10) 0.0386(10)
_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
Cl1 C18 1.7451(19) . ?
Cl2 C20 1.742(2) . ?
S1 C6 1.7581(19) . ?
S1 C7 1.8184(19) . ?
O1 C8 1.219(2) . ?
N1 C1 1.374(2) . ?
N1 C16 1.449(2) . ?
N1 H1 0.8600 . ?
C1 C6 1.397(3) . ?
C1 C2 1.402(3) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.517(3) . ?
C7 C16 1.540(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.482(3) . ?
C9 C10 1.390(3) . ?
C9 C14 1.391(3) . ?
C10 C11 1.378(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(3) . ?
C12 C15 1.508(3) . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.516(3) . ?
C16 H16 0.9800 . ?
C17 C18 1.385(3) . ?
C17 C22 1.392(3) . ?
C18 C19 1.383(3) . ?
C19 C20 1.372(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.370(3) . ?
C21 C22 1.375(3) . ?
C21 H21 0.9300 . ?
C22 H22 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
C6 S1 C7 98.55(8) . . ?
C1 N1 C16 127.18(16) . . ?
C1 N1 H1 116.4 . . ?
C16 N1 H1 116.4 . . ?
N1 C1 C6 122.93(17) . . ?
N1 C1 C2 119.26(18) . . ?
C6 C1 C2 117.79(18) . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.3(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 120.42(19) . . ?
C5 C6 S1 119.26(16) . . ?
C1 C6 S1 120.23(14) . . ?
C8 C7 C16 112.48(14) . . ?
C8 C7 S1 109.74(12) . . ?
C16 C7 S1 111.74(13) . . ?
C8 C7 H7 107.5 . . ?
C16 C7 H7 107.5 . . ?
S1 C7 H7 107.5 . . ?
O1 C8 C9 120.74(18) . . ?
O1 C8 C7 119.43(17) . . ?
C9 C8 C7 119.84(15) . . ?
C10 C9 C14 117.88(18) . . ?
C10 C9 C8 118.25(17) . . ?
C14 C9 C8 123.86(17) . . ?
C11 C10 C9 121.38(19) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 117.90(19) . . ?
C13 C12 C15 121.4(2) . . ?
C11 C12 C15 120.7(2) . . ?
C14 C13 C12 122.08(19) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C9 120.16(19) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C17 111.80(15) . . ?
N1 C16 C7 113.96(15) . . ?
C17 C16 C7 110.51(14) . . ?
N1 C16 H16 106.7 . . ?
C17 C16 H16 106.7 . . ?
C7 C16 H16 106.7 . . ?
C18 C17 C22 116.41(17) . . ?
C18 C17 C16 121.91(16) . . ?
C22 C17 C16 121.67(16) . . ?
C19 C18 C17 122.62(18) . . ?
C19 C18 Cl1 117.09(15) . . ?
C17 C18 Cl1 120.24(15) . . ?
C20 C19 C18 118.47(19) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C21 C20 C19 121.10(19) . . ?
C21 C20 Cl2 118.89(17) . . ?
C19 C20 Cl2 119.98(17) . . ?
C20 C21 C22 119.28(19) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C17 122.04(18) . . ?
C21 C22 H22 119.0 . . ?
C17 C22 H22 119.0 . . ?
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
C16 N1 C1 C6 17.1(3) . . . . ?
C16 N1 C1 C2 -164.69(18) . . . . ?
N1 C1 C2 C3 -177.33(19) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 2.2(3) . . . . ?
C4 C5 C6 C1 -2.2(3) . . . . ?
C4 C5 C6 S1 174.37(17) . . . . ?
N1 C1 C6 C5 178.86(18) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
N1 C1 C6 S1 2.3(3) . . . . ?
C2 C1 C6 S1 -175.91(14) . . . . ?
C7 S1 C6 C5 149.21(16) . . . . ?
C7 S1 C6 C1 -34.21(17) . . . . ?
C6 S1 C7 C8 -71.38(14) . . . . ?
C6 S1 C7 C16 54.09(14) . . . . ?
C16 C7 C8 O1 -28.5(2) . . . . ?
S1 C7 C8 O1 96.52(18) . . . . ?
C16 C7 C8 C9 151.16(16) . . . . ?
S1 C7 C8 C9 -83.78(18) . . . . ?
O1 C8 C9 C10 6.6(3) . . . . ?
C7 C8 C9 C10 -173.07(17) . . . . ?
O1 C8 C9 C14 -173.51(19) . . . . ?
C7 C8 C9 C14 6.8(3) . . . . ?
C14 C9 C10 C11 1.2(3) . . . . ?
C8 C9 C10 C11 -178.97(19) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C13 -1.5(3) . . . . ?
C10 C11 C12 C15 176.9(2) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C15 C12 C13 C14 -177.4(2) . . . . ?
C12 C13 C14 C9 0.6(3) . . . . ?
C10 C9 C14 C13 -1.7(3) . . . . ?
C8 C9 C14 C13 178.47(18) . . . . ?
C1 N1 C16 C17 -118.7(2) . . . . ?
C1 N1 C16 C7 7.5(3) . . . . ?
C8 C7 C16 N1 78.7(2) . . . . ?
S1 C7 C16 N1 -45.29(19) . . . . ?
C8 C7 C16 C17 -154.46(15) . . . . ?
S1 C7 C16 C17 81.59(16) . . . . ?
N1 C16 C17 C18 -153.82(17) . . . . ?
C7 C16 C17 C18 78.1(2) . . . . ?
N1 C16 C17 C22 24.7(2) . . . . ?
C7 C16 C17 C22 -103.33(19) . . . . ?
C22 C17 C18 C19 -2.9(3) . . . . ?
C16 C17 C18 C19 175.69(17) . . . . ?
C22 C17 C18 Cl1 179.69(14) . . . . ?
C16 C17 C18 Cl1 -1.7(2) . . . . ?
C17 C18 C19 C20 2.3(3) . . . . ?
Cl1 C18 C19 C20 179.78(16) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C18 C19 C20 Cl2 -177.88(15) . . . . ?
C19 C20 C21 C22 -1.8(3) . . . . ?
Cl2 C20 C21 C22 176.26(16) . . . . ?
C20 C21 C22 C17 1.1(3) . . . . ?
C18 C17 C22 C21 1.2(3) . . . . ?
C16 C17 C22 C21 -177.43(17) . . . . ?
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.037