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


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#
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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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#  fide research purposes only. It may contain copyright material 
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data_ba23
_database_code_depnum_ccdc_archive 'CCDC 900519'
#TrackingRef 'web_deposit_cif_file_0_Damir_1360705793.DDDS55.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 N O S'
_chemical_formula_sum            'C16 H13 N O S'
_chemical_formula_weight         267.33
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'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   9.8568(12)
_cell_length_b                   9.8036(10)
_cell_length_c                   13.8407(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.520(10)
_cell_angle_gamma                90.00
_cell_volume                     1268.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6779
_cell_measurement_theta_min      3.68
_cell_measurement_theta_max      26.12
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9619
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Genix 3D I\mS microfocus X-ray source'
_diffrn_radiation_monochromator  'Genix 3D multilayer optics'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7456
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_sigmaI/netI    0.0611
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.69
_diffrn_reflns_theta_max         25.59
_reflns_number_total             2354
_reflns_number_gt                1802
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL97
_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^)+(0.0851P)^2^+0.0442P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2354
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1318
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
O1 O 0.64540(17) 0.65605(19) 0.26735(14) 0.0338(5) Uani 1 1 d . . .
N1 N 0.3978(2) 0.5419(2) 0.18528(15) 0.0254(5) Uani 1 1 d . . .
H1 H 0.468(4) 0.602(4) 0.184(3) 0.054(10) Uiso 1 1 d . . .
C1 C 0.4325(2) 0.4660(2) 0.26718(17) 0.0229(5) Uani 1 1 d . . .
H1A H 0.3664 0.3977 0.2718 0.027 Uiso 1 1 calc R . .
C2 C 0.2646(2) 0.5249(3) 0.10000(18) 0.0309(6) Uani 1 1 d . A .
H2A H 0.2574 0.4289 0.0767 0.037 Uiso 1 1 calc R . .
H2B H 0.2690 0.5831 0.0426 0.037 Uiso 1 1 calc R . .
C11 C 0.5601(2) 0.4778(2) 0.34870(17) 0.0218(5) Uani 1 1 d . . .
C12 C 0.6641(2) 0.5771(2) 0.34268(18) 0.0240(5) Uani 1 1 d . . .
C13 C 0.7956(2) 0.5841(3) 0.42741(19) 0.0286(6) Uani 1 1 d . . .
H13 H 0.8673 0.6476 0.4250 0.034 Uiso 1 1 calc R . .
C14 C 0.8188(2) 0.5029(3) 0.50941(18) 0.0280(6) Uani 1 1 d . . .
H14 H 0.9065 0.5115 0.5634 0.034 Uiso 1 1 calc R . .
C15 C 0.7171(2) 0.4046(2) 0.51856(17) 0.0232(5) Uani 1 1 d . . .
C16 C 0.7445(2) 0.3228(3) 0.60637(18) 0.0271(5) Uani 1 1 d . . .
H16 H 0.8326 0.3328 0.6598 0.033 Uiso 1 1 calc R . .
C17 C 0.6475(3) 0.2297(3) 0.61631(19) 0.0322(6) Uani 1 1 d . . .
H17 H 0.6669 0.1754 0.6760 0.039 Uiso 1 1 calc R . .
C18 C 0.5185(3) 0.2155(3) 0.5369(2) 0.0315(6) Uani 1 1 d . . .
H18 H 0.4503 0.1503 0.5428 0.038 Uiso 1 1 calc R . .
C19 C 0.4885(2) 0.2937(3) 0.45062(17) 0.0255(5) Uani 1 1 d . . .
H19 H 0.3997 0.2820 0.3982 0.031 Uiso 1 1 calc R . .
C20 C 0.5863(2) 0.3908(2) 0.43810(16) 0.0204(5) Uani 1 1 d . . .
C21 C 0.1322(2) 0.5606(3) 0.12615(17) 0.0256(5) Uani 1 1 d . . .
S22 S 0.06735(11) 0.71283(11) 0.11964(8) 0.0378(4) Uani 0.546(4) 1 d P A 1
C22' C 0.06735(11) 0.71283(11) 0.11964(8) 0.0378(4) Uani 0.454(4) 1 d P A 2
H22' H 0.0998 0.7970 0.1009 0.045 Uiso 0.454(4) 1 calc PR A 2
C23 C -0.0638(3) 0.6789(4) 0.1534(3) 0.0550(10) Uani 1 1 d . . .
H23 H -0.1309 0.7465 0.1573 0.066 Uiso 1 1 calc R A 1
C24 C -0.0768(3) 0.5499(5) 0.1766(2) 0.0611(11) Uani 1 1 d . A .
H24 H -0.1527 0.5196 0.1997 0.073 Uiso 1 1 calc R B 1
C25 C 0.03805(13) 0.45209(13) 0.16413(9) 0.0394(5) Uani 0.546(4) 1 d P A 1
H25 H 0.0498 0.3566 0.1754 0.047 Uiso 0.546(4) 1 calc PR A 1
S25' S 0.03805(13) 0.45209(13) 0.16413(9) 0.0394(5) Uani 0.454(4) 1 d P A 2
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
O1 0.0276(9) 0.0331(10) 0.0376(10) 0.0133(8) 0.0061(7) -0.0013(7)
N1 0.0202(9) 0.0311(12) 0.0231(10) 0.0001(8) 0.0044(7) 0.0037(9)
C1 0.0203(10) 0.0224(12) 0.0257(11) -0.0035(9) 0.0069(9) 0.0012(9)
C2 0.0221(11) 0.0462(16) 0.0218(11) -0.0032(11) 0.0034(9) 0.0037(11)
C11 0.0188(10) 0.0202(12) 0.0259(11) -0.0026(9) 0.0063(9) 0.0029(9)
C12 0.0217(11) 0.0218(12) 0.0280(12) 0.0005(9) 0.0073(9) 0.0030(9)
C13 0.0200(11) 0.0272(13) 0.0358(13) 0.0010(10) 0.0047(9) -0.0044(9)
C14 0.0189(11) 0.0272(13) 0.0309(12) -0.0024(10) -0.0019(9) 0.0006(9)
C15 0.0224(11) 0.0214(12) 0.0238(11) -0.0032(9) 0.0045(9) 0.0041(9)
C16 0.0266(11) 0.0300(13) 0.0218(11) -0.0003(9) 0.0035(9) 0.0076(10)
C17 0.0373(13) 0.0332(15) 0.0278(12) 0.0072(10) 0.0126(10) 0.0089(11)
C18 0.0321(12) 0.0299(14) 0.0364(13) 0.0016(11) 0.0167(10) -0.0028(11)
C19 0.0225(10) 0.0289(13) 0.0243(11) -0.0006(9) 0.0064(9) -0.0015(10)
C20 0.0195(10) 0.0202(12) 0.0224(10) -0.0046(9) 0.0079(8) 0.0047(9)
C21 0.0206(10) 0.0334(14) 0.0179(10) -0.0004(9) -0.0005(8) 0.0002(9)
S22 0.0345(6) 0.0386(7) 0.0348(6) 0.0059(4) 0.0032(4) 0.0121(4)
C22' 0.0345(6) 0.0386(7) 0.0348(6) 0.0059(4) 0.0032(4) 0.0121(4)
C23 0.0301(14) 0.076(3) 0.0481(17) -0.0201(17) -0.0030(13) 0.0206(16)
C24 0.0315(15) 0.117(4) 0.0359(16) -0.0190(19) 0.0132(12) -0.0309(18)
C25 0.0403(7) 0.0373(8) 0.0393(7) -0.0027(5) 0.0107(5) -0.0043(5)
S25' 0.0403(7) 0.0373(8) 0.0393(7) -0.0027(5) 0.0107(5) -0.0043(5)
_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
O1 C12 1.264(3) . ?
N1 C1 1.308(3) . ?
N1 C2 1.470(3) . ?
N1 H1 0.92(4) . ?
C1 C11 1.402(3) . ?
C1 H1A 0.9500 . ?
C2 C21 1.502(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C11 C12 1.436(3) . ?
C11 C20 1.456(3) . ?
C12 C13 1.447(3) . ?
C13 C14 1.345(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.425(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.409(3) . ?
C15 C20 1.417(3) . ?
C16 C17 1.360(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.399(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.369(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.405(3) . ?
C19 H19 0.9500 . ?
C21 C25 1.606(3) . ?
C21 S22 1.615(3) . ?
S22 C23 1.544(4) . ?
C23 C24 1.320(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.535(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
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
C1 N1 C2 123.5(2) . . ?
C1 N1 H1 113(2) . . ?
C2 N1 H1 123(2) . . ?
N1 C1 C11 124.9(2) . . ?
N1 C1 H1A 117.6 . . ?
C11 C1 H1A 117.6 . . ?
N1 C2 C21 113.77(19) . . ?
N1 C2 H2A 108.8 . . ?
C21 C2 H2A 108.8 . . ?
N1 C2 H2B 108.8 . . ?
C21 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C1 C11 C12 118.9(2) . . ?
C1 C11 C20 120.5(2) . . ?
C12 C11 C20 120.60(19) . . ?
O1 C12 C11 122.9(2) . . ?
O1 C12 C13 119.8(2) . . ?
C11 C12 C13 117.2(2) . . ?
C14 C13 C12 121.6(2) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 122.7(2) . . ?
C13 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C16 C15 C20 120.0(2) . . ?
C16 C15 C14 121.0(2) . . ?
C20 C15 C14 119.0(2) . . ?
C17 C16 C15 121.4(2) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 118.7(2) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C19 C18 C17 121.4(2) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 121.3(2) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C15 117.2(2) . . ?
C19 C20 C11 123.92(19) . . ?
C15 C20 C11 118.9(2) . . ?
C2 C21 C25 124.1(2) . . ?
C2 C21 S22 124.1(2) . . ?
C25 C21 S22 111.76(16) . . ?
C23 S22 C21 97.96(18) . . ?
C24 C23 S22 115.8(3) . . ?
C24 C23 H23 122.1 . . ?
S22 C23 H23 122.1 . . ?
C23 C24 C25 116.0(3) . . ?
C23 C24 H24 122.0 . . ?
C25 C24 H24 122.0 . . ?
C24 C25 C21 98.44(19) . . ?
C24 C25 H25 130.8 . . ?
C21 C25 H25 130.8 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 C11 178.6(2) . . . . ?
C1 N1 C2 C21 67.6(3) . . . . ?
N1 C1 C11 C12 -1.9(4) . . . . ?
N1 C1 C11 C20 178.0(2) . . . . ?
C1 C11 C12 O1 0.8(4) . . . . ?
C20 C11 C12 O1 -179.0(2) . . . . ?
C1 C11 C12 C13 -178.7(2) . . . . ?
C20 C11 C12 C13 1.4(3) . . . . ?
O1 C12 C13 C14 179.2(3) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C16 -179.1(2) . . . . ?
C13 C14 C15 C20 0.3(4) . . . . ?
C20 C15 C16 C17 -0.1(4) . . . . ?
C14 C15 C16 C17 179.3(2) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C20 0.4(4) . . . . ?
C18 C19 C20 C15 -0.1(3) . . . . ?
C18 C19 C20 C11 -179.4(2) . . . . ?
C16 C15 C20 C19 0.0(3) . . . . ?
C14 C15 C20 C19 -179.4(2) . . . . ?
C16 C15 C20 C11 179.3(2) . . . . ?
C14 C15 C20 C11 0.0(3) . . . . ?
C1 C11 C20 C19 -1.4(3) . . . . ?
C12 C11 C20 C19 178.5(2) . . . . ?
C1 C11 C20 C15 179.3(2) . . . . ?
C12 C11 C20 C15 -0.8(3) . . . . ?
N1 C2 C21 C25 -93.6(3) . . . . ?
N1 C2 C21 S22 86.3(3) . . . . ?
C2 C21 S22 C23 179.1(2) . . . . ?
C25 C21 S22 C23 -0.94(18) . . . . ?
C21 S22 C23 C24 1.4(3) . . . . ?
S22 C23 C24 C25 -1.5(4) . . . . ?
C23 C24 C25 C21 0.7(3) . . . . ?
C2 C21 C25 C24 -179.8(2) . . . . ?
S22 C21 C25 C24 0.29(18) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.92(4) 1.84(4) 2.596(3) 139(3) .
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.055


data_ba11
_database_code_depnum_ccdc_archive 'CCDC 924293'
#TrackingRef 'web_deposit_cif_file_1_Damir_1360705793.DDC5.cif'
# start Validation Reply Form
_vrf_PLAT355_I                   
;
PROBLEM: Long O-H Bond (0.82A) O1A - H1O ... 1.17 Ang.
RESPONSE: This H atom is almost in the middle of two O atoms.
It has been freely refined.
;
# end Validation Reply Form
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 N O S, C16 H14 N O S, Cl O4'
_chemical_formula_sum            'C32 H27 Cl N2 O6 S2'
_chemical_formula_weight         635.13
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'
Cl Cl 0.1484 0.1585 '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
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   10.5023(7)
_cell_length_b                   10.7351(7)
_cell_length_c                   13.3354(9)
_cell_angle_alpha                101.051(5)
_cell_angle_beta                 93.924(5)
_cell_angle_gamma                101.720(5)
_cell_volume                     1435.79(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    28003
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      26.0
_exptl_crystal_description       block
_exptl_crystal_colour            orange-brown
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9049
_exptl_absorpt_correction_T_max  0.9523
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Genix 3D I\mS microfocus X-ray source'
_diffrn_radiation_monochromator  'Genix 3D multilayer optics'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26146
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         25.65
_reflns_number_total             5392
_reflns_number_gt                4710
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  SHELXL97
_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^)+(0.0532P)^2^+0.7299P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5392
_refine_ls_number_parameters     402
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.37632(5) 0.06407(5) 0.77065(4) 0.03499(19) Uani 0.928(3) 1 d P A 1
C14' C 0.37632(5) 0.06407(5) 0.77065(4) 0.03499(19) Uani 0.072(3) 1 d P A 2
H14' H 0.4488 0.0236 0.7699 0.042 Uiso 0.072(3) 1 calc PR A 2
O1 O 0.51812(13) 0.27881(13) 0.50594(10) 0.0314(3) Uani 1 1 d . . .
N1 N 0.52583(16) 0.35051(16) 0.70267(12) 0.0299(3) Uani 1 1 d . . .
H1 H 0.499(2) 0.296(2) 0.650(2) 0.040(6) Uiso 1 1 d . . .
C1 C 0.59861(17) 0.38802(18) 0.50491(14) 0.0267(4) Uani 1 1 d . . .
C2 C 0.63809(18) 0.41822(19) 0.41035(14) 0.0312(4) Uani 1 1 d . . .
H2 H 0.6082 0.3565 0.3477 0.037 Uiso 1 1 calc R . .
C3 C 0.71744(19) 0.5335(2) 0.40915(14) 0.0320(4) Uani 1 1 d . . .
H3 H 0.7397 0.5519 0.3449 0.038 Uiso 1 1 calc R . .
C4 C 0.76945(17) 0.62931(18) 0.50065(14) 0.0281(4) Uani 1 1 d . . .
C5 C 0.85174(19) 0.7489(2) 0.49657(16) 0.0337(4) Uani 1 1 d . . .
H5 H 0.8688 0.7687 0.4317 0.040 Uiso 1 1 calc R . .
C6 C 0.9075(2) 0.8370(2) 0.58459(16) 0.0365(4) Uani 1 1 d . . .
H6 H 0.9627 0.9177 0.5811 0.044 Uiso 1 1 calc R . .
C7 C 0.8822(2) 0.80688(19) 0.67964(16) 0.0357(4) Uani 1 1 d . . .
H7 H 0.9227 0.8666 0.7410 0.043 Uiso 1 1 calc R . .
C8 C 0.79969(19) 0.69240(18) 0.68587(14) 0.0313(4) Uani 1 1 d . . .
H8 H 0.7837 0.6746 0.7515 0.038 Uiso 1 1 calc R . .
C9 C 0.73831(17) 0.60077(17) 0.59666(13) 0.0261(4) Uani 1 1 d . . .
C10 C 0.64823(17) 0.47959(17) 0.59810(13) 0.0252(4) Uani 1 1 d . . .
C11 C 0.60684(17) 0.45450(18) 0.69173(14) 0.0276(4) Uani 1 1 d . . .
H11 H 0.6410 0.5191 0.7521 0.033 Uiso 1 1 calc R . .
C12 C 0.4794(2) 0.3305(2) 0.80109(15) 0.0391(5) Uani 1 1 d . A .
H12A H 0.4582 0.4116 0.8381 0.047 Uiso 1 1 calc R . .
H12B H 0.5497 0.3101 0.8442 0.047 Uiso 1 1 calc R . .
C13 C 0.36094(19) 0.22222(18) 0.78454(13) 0.0306(4) Uani 1 1 d . . .
C14 C 0.23138(18) 0.23344(19) 0.78067(13) 0.0418(6) Uani 0.928(3) 1 d P A 1
H14 H 0.2027 0.3127 0.7872 0.050 Uiso 0.928(3) 1 calc PR A 1
S1' S 0.23138(18) 0.23344(19) 0.78067(13) 0.0418(6) Uani 0.072(3) 1 d P A 2
C15 C 0.1469(2) 0.1051(2) 0.76517(15) 0.0361(4) Uani 1 1 d . . .
H15 H 0.0541 0.0908 0.7600 0.043 Uiso 1 1 calc R A 1
C16 C 0.2110(2) 0.0078(2) 0.75865(15) 0.0367(4) Uani 1 1 d . A .
H16 H 0.1691 -0.0815 0.7486 0.044 Uiso 1 1 calc R B 1
S1A S 0.10678(7) 0.17114(7) 0.03640(5) 0.0427(2) Uani 0.781(3) 1 d P C 1
C14" C 0.10678(7) 0.17114(7) 0.03640(5) 0.0427(2) Uani 0.219(3) 1 d P C 2
H14" H 0.0364 0.0996 0.0357 0.051 Uiso 0.219(3) 1 calc PR C 2
O1A O 0.42409(13) 0.12394(13) 0.34528(10) 0.0326(3) Uani 1 1 d . . .
H1O H 0.468(4) 0.198(4) 0.422(3) 0.098(12) Uiso 1 1 d . . .
N1A N 0.34853(18) 0.05241(17) 0.14669(13) 0.0341(4) Uani 1 1 d . . .
H1A H 0.397(3) 0.108(3) 0.191(2) 0.050(7) Uiso 1 1 d . . .
C1A C 0.34925(18) 0.01599(18) 0.35847(14) 0.0286(4) Uani 1 1 d . . .
C2A C 0.33527(19) -0.00902(19) 0.45841(15) 0.0335(4) Uani 1 1 d . . .
H2A H 0.3807 0.0534 0.5168 0.040 Uiso 1 1 calc R . .
C3A C 0.2581(2) -0.1206(2) 0.47133(16) 0.0355(4) Uani 1 1 d . . .
H3A H 0.2508 -0.1345 0.5391 0.043 Uiso 1 1 calc R . .
C4A C 0.18736(18) -0.21828(19) 0.38704(16) 0.0335(4) Uani 1 1 d . . .
C5A C 0.1084(2) -0.3343(2) 0.40329(19) 0.0414(5) Uani 1 1 d . . .
H5A H 0.1033 -0.3481 0.4713 0.050 Uiso 1 1 calc R . .
C6A C 0.0394(2) -0.4271(2) 0.3225(2) 0.0466(6) Uani 1 1 d . . .
H6A H -0.0145 -0.5043 0.3342 0.056 Uiso 1 1 calc R . .
C7A C 0.0489(2) -0.4073(2) 0.2228(2) 0.0481(6) Uani 1 1 d . . .
H7A H 0.0005 -0.4716 0.1667 0.058 Uiso 1 1 calc R . .
C8A C 0.1266(2) -0.2969(2) 0.20420(18) 0.0413(5) Uani 1 1 d . . .
H8A H 0.1328 -0.2868 0.1353 0.050 Uiso 1 1 calc R . .
C9A C 0.19785(18) -0.19749(18) 0.28638(15) 0.0313(4) Uani 1 1 d . . .
C10A C 0.27947(18) -0.07667(18) 0.27187(14) 0.0293(4) Uani 1 1 d . . .
C11A C 0.28149(19) -0.04934(19) 0.17217(15) 0.0318(4) Uani 1 1 d . . .
H11A H 0.2276 -0.1128 0.1181 0.038 Uiso 1 1 calc R . .
C12A C 0.3386(2) 0.0783(2) 0.04289(15) 0.0386(5) Uani 1 1 d . C .
H12C H 0.2876 -0.0006 -0.0056 0.046 Uiso 1 1 calc R . .
H12D H 0.4273 0.0990 0.0210 0.046 Uiso 1 1 calc R . .
C13A C 0.2736(2) 0.1893(2) 0.03909(14) 0.0344(4) Uani 1 1 d . . .
C14A C 0.3469(2) 0.32885(17) 0.04133(11) 0.0596(6) Uani 0.781(3) 1 d P C 1
H14A H 0.4383 0.3627 0.0444 0.071 Uiso 0.781(3) 1 calc PR C 1
S1" S 0.3469(2) 0.32885(17) 0.04133(11) 0.0596(6) Uani 0.219(3) 1 d P C 2
C15A C 0.2381(3) 0.3970(2) 0.03750(16) 0.0456(5) Uani 1 1 d . . .
H15A H 0.2540 0.4871 0.0365 0.055 Uiso 1 1 calc R C 1
C16A C 0.1165(3) 0.3272(3) 0.03551(17) 0.0506(6) Uani 1 1 d . C .
H16A H 0.0416 0.3641 0.0337 0.061 Uiso 1 1 calc R D 1
Cl1 Cl 0.29524(5) 0.70488(5) 0.88968(4) 0.03845(14) Uani 1 1 d . . .
O11 O 0.2909(3) 0.57217(17) 0.84909(15) 0.0764(7) Uani 1 1 d . . .
O12 O 0.37646(17) 0.78470(17) 0.83452(13) 0.0536(4) Uani 1 1 d . . .
O13 O 0.1702(2) 0.7325(3) 0.8856(3) 0.1179(11) Uani 1 1 d . . .
O14 O 0.3507(2) 0.7366(2) 0.99539(13) 0.0696(6) Uani 1 1 d . . .
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 0.0352(3) 0.0286(3) 0.0406(3) 0.0078(2) 0.0070(2) 0.0043(2)
C14' 0.0352(3) 0.0286(3) 0.0406(3) 0.0078(2) 0.0070(2) 0.0043(2)
O1 0.0331(7) 0.0280(7) 0.0272(7) 0.0012(5) 0.0002(5) -0.0014(5)
N1 0.0336(8) 0.0286(8) 0.0228(8) 0.0031(7) 0.0011(6) -0.0011(7)
C1 0.0239(8) 0.0276(9) 0.0273(9) 0.0034(7) 0.0008(7) 0.0058(7)
C2 0.0311(10) 0.0365(10) 0.0232(9) 0.0015(7) 0.0008(7) 0.0065(8)
C3 0.0313(10) 0.0405(11) 0.0244(9) 0.0081(8) 0.0039(7) 0.0070(8)
C4 0.0253(9) 0.0314(10) 0.0294(9) 0.0081(7) 0.0046(7) 0.0082(7)
C5 0.0317(10) 0.0354(10) 0.0359(10) 0.0122(8) 0.0085(8) 0.0054(8)
C6 0.0334(10) 0.0303(10) 0.0448(11) 0.0093(8) 0.0100(9) 0.0011(8)
C7 0.0343(10) 0.0301(10) 0.0367(10) -0.0002(8) 0.0059(8) -0.0004(8)
C8 0.0327(10) 0.0294(10) 0.0284(9) 0.0027(7) 0.0051(7) 0.0019(8)
C9 0.0242(8) 0.0272(9) 0.0272(9) 0.0042(7) 0.0042(7) 0.0074(7)
C10 0.0233(8) 0.0266(9) 0.0249(8) 0.0036(7) 0.0022(7) 0.0058(7)
C11 0.0270(9) 0.0263(9) 0.0261(9) 0.0025(7) -0.0007(7) 0.0021(7)
C12 0.0465(12) 0.0383(11) 0.0242(9) 0.0062(8) 0.0021(8) -0.0086(9)
C13 0.0391(10) 0.0277(9) 0.0220(8) 0.0061(7) 0.0040(7) -0.0004(8)
C14 0.0471(11) 0.0443(11) 0.0315(10) 0.0087(7) 0.0050(7) 0.0034(8)
S1' 0.0471(11) 0.0443(11) 0.0315(10) 0.0087(7) 0.0050(7) 0.0034(8)
C15 0.0330(10) 0.0390(11) 0.0341(10) 0.0078(8) 0.0056(8) 0.0021(8)
C16 0.0386(11) 0.0295(10) 0.0370(10) 0.0054(8) 0.0060(8) -0.0035(8)
S1A 0.0459(4) 0.0405(4) 0.0343(4) -0.0009(3) -0.0024(3) 0.0029(3)
C14" 0.0459(4) 0.0405(4) 0.0343(4) -0.0009(3) -0.0024(3) 0.0029(3)
O1A 0.0365(7) 0.0273(7) 0.0280(7) 0.0009(5) 0.0001(5) -0.0010(6)
N1A 0.0418(10) 0.0292(9) 0.0267(8) 0.0004(7) -0.0005(7) 0.0038(7)
C1A 0.0279(9) 0.0257(9) 0.0299(9) 0.0015(7) 0.0011(7) 0.0058(7)
C2A 0.0348(10) 0.0331(10) 0.0300(10) 0.0028(8) -0.0001(8) 0.0063(8)
C3A 0.0368(11) 0.0371(11) 0.0348(10) 0.0100(8) 0.0058(8) 0.0102(9)
C4A 0.0266(9) 0.0312(10) 0.0441(11) 0.0078(8) 0.0065(8) 0.0091(8)
C5A 0.0314(10) 0.0376(11) 0.0595(14) 0.0156(10) 0.0116(9) 0.0106(9)
C6A 0.0297(10) 0.0297(11) 0.0808(17) 0.0109(11) 0.0143(11) 0.0050(8)
C7A 0.0347(11) 0.0320(11) 0.0674(16) -0.0059(10) 0.0053(10) -0.0003(9)
C8A 0.0373(11) 0.0318(11) 0.0470(12) -0.0039(9) 0.0033(9) 0.0015(9)
C9A 0.0250(9) 0.0277(9) 0.0389(10) 0.0011(8) 0.0034(8) 0.0063(7)
C10A 0.0271(9) 0.0268(9) 0.0310(9) -0.0001(7) 0.0016(7) 0.0056(7)
C11A 0.0306(9) 0.0295(10) 0.0300(9) -0.0039(7) 0.0002(7) 0.0053(8)
C12A 0.0530(13) 0.0350(11) 0.0246(9) 0.0009(8) 0.0043(8) 0.0074(9)
C13A 0.0432(11) 0.0350(10) 0.0209(8) 0.0018(7) 0.0022(8) 0.0035(9)
C14A 0.0921(14) 0.0631(11) 0.0303(8) 0.0072(6) 0.0115(7) 0.0337(9)
S1" 0.0921(14) 0.0631(11) 0.0303(8) 0.0072(6) 0.0115(7) 0.0337(9)
C15A 0.0679(16) 0.0356(11) 0.0306(10) 0.0048(9) 0.0021(10) 0.0081(11)
C16A 0.0560(15) 0.0592(15) 0.0341(11) -0.0004(10) -0.0032(10) 0.0196(12)
Cl1 0.0409(3) 0.0290(3) 0.0444(3) 0.0099(2) 0.0098(2) 0.0017(2)
O11 0.139(2) 0.0273(9) 0.0548(11) 0.0039(8) 0.0131(12) 0.0038(10)
O12 0.0579(10) 0.0469(9) 0.0532(10) 0.0204(8) 0.0115(8) -0.0055(8)
O13 0.0440(12) 0.124(2) 0.210(3) 0.083(2) 0.0264(16) 0.0257(13)
O14 0.1020(16) 0.0656(12) 0.0348(9) 0.0047(8) 0.0140(9) 0.0074(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 C16 1.704(2) . ?
S1 C13 1.714(2) . ?
O1 C1 1.302(2) . ?
O1 H1O 1.29(4) . ?
N1 C11 1.298(2) . ?
N1 C12 1.470(2) . ?
N1 H1 0.81(3) . ?
C1 C10 1.420(2) . ?
C1 C2 1.429(3) . ?
C2 C3 1.348(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.430(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.407(3) . ?
C4 C9 1.417(3) . ?
C5 C6 1.368(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.410(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.449(3) . ?
C10 C11 1.406(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.492(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.389(3) . ?
C14 C15 1.448(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.345(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
S1A C16A 1.660(3) . ?
S1A C13A 1.720(2) . ?
O1A C1A 1.311(2) . ?
O1A H1O 1.17(4) . ?
N1A C11A 1.291(3) . ?
N1A C12A 1.464(3) . ?
N1A H1A 0.82(3) . ?
C1A C10A 1.417(3) . ?
C1A C2A 1.421(3) . ?
C2A C3A 1.351(3) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.426(3) . ?
C3A H3A 0.9500 . ?
C4A C9A 1.410(3) . ?
C4A C5A 1.412(3) . ?
C5A C6A 1.366(3) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.392(4) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.371(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.420(3) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.457(3) . ?
C10A C11A 1.416(3) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.496(3) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C13A C14A 1.533(3) . ?
C14A C15A 1.480(3) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.339(4) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
Cl1 O13 1.404(2) . ?
Cl1 O11 1.4141(18) . ?
Cl1 O12 1.4260(16) . ?
Cl1 O14 1.4372(19) . ?
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
C16 S1 C13 91.99(10) . . ?
C1 O1 H1O 120.8(16) . . ?
C11 N1 C12 123.98(17) . . ?
C11 N1 H1 115.5(17) . . ?
C12 N1 H1 120.5(17) . . ?
O1 C1 C10 120.38(16) . . ?
O1 C1 C2 120.76(16) . . ?
C10 C1 C2 118.86(16) . . ?
C3 C2 C1 120.60(17) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 122.72(17) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C5 C4 C9 120.17(17) . . ?
C5 C4 C3 121.22(17) . . ?
C9 C4 C3 118.60(17) . . ?
C6 C5 C4 121.04(18) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.06(18) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 121.12(19) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 121.22(18) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C4 117.27(17) . . ?
C8 C9 C10 123.86(16) . . ?
C4 C9 C10 118.87(16) . . ?
C11 C10 C1 119.96(16) . . ?
C11 C10 C9 119.81(16) . . ?
C1 C10 C9 120.21(16) . . ?
N1 C11 C10 125.48(17) . . ?
N1 C11 H11 117.3 . . ?
C10 C11 H11 117.3 . . ?
N1 C12 C13 110.98(16) . . ?
N1 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
N1 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 126.83(19) . . ?
C14 C13 S1 112.67(14) . . ?
C12 C13 S1 120.49(16) . . ?
C13 C14 C15 109.23(17) . . ?
C13 C14 H14 125.4 . . ?
C15 C14 H14 125.4 . . ?
C16 C15 C14 114.19(18) . . ?
C16 C15 H15 122.9 . . ?
C14 C15 H15 122.9 . . ?
C15 C16 S1 111.92(15) . . ?
C15 C16 H16 124.0 . . ?
S1 C16 H16 124.0 . . ?
C16A S1A C13A 92.12(12) . . ?
C1A O1A H1O 114.0(18) . . ?
C11A N1A C12A 123.96(18) . . ?
C11A N1A H1A 118.7(19) . . ?
C12A N1A H1A 117.2(19) . . ?
O1A C1A C10A 119.62(17) . . ?
O1A C1A C2A 121.11(16) . . ?
C10A C1A C2A 119.27(17) . . ?
C3A C2A C1A 120.73(18) . . ?
C3A C2A H2A 119.6 . . ?
C1A C2A H2A 119.6 . . ?
C2A C3A C4A 122.47(19) . . ?
C2A C3A H3A 118.8 . . ?
C4A C3A H3A 118.8 . . ?
C9A C4A C5A 120.22(19) . . ?
C9A C4A C3A 118.80(18) . . ?
C5A C4A C3A 121.0(2) . . ?
C6A C5A C4A 120.9(2) . . ?
C6A C5A H5A 119.6 . . ?
C4A C5A H5A 119.6 . . ?
C5A C6A C7A 119.3(2) . . ?
C5A C6A H6A 120.3 . . ?
C7A C6A H6A 120.3 . . ?
C8A C7A C6A 121.3(2) . . ?
C8A C7A H7A 119.4 . . ?
C6A C7A H7A 119.4 . . ?
C7A C8A C9A 120.9(2) . . ?
C7A C8A H8A 119.6 . . ?
C9A C8A H8A 119.6 . . ?
C4A C9A C8A 117.36(19) . . ?
C4A C9A C10A 119.07(17) . . ?
C8A C9A C10A 123.57(19) . . ?
C11A C10A C1A 120.63(17) . . ?
C11A C10A C9A 119.61(17) . . ?
C1A C10A C9A 119.63(17) . . ?
N1A C11A C10A 127.09(18) . . ?
N1A C11A H11A 116.5 . . ?
C10A C11A H11A 116.5 . . ?
N1A C12A C13A 111.15(16) . . ?
N1A C12A H12C 109.4 . . ?
C13A C12A H12C 109.4 . . ?
N1A C12A H12D 109.4 . . ?
C13A C12A H12D 109.4 . . ?
H12C C12A H12D 108.0 . . ?
C12A C13A C14A 124.28(18) . . ?
C12A C13A S1A 121.92(16) . . ?
C14A C13A S1A 113.75(15) . . ?
C15A C14A C13A 101.79(17) . . ?
C15A C14A H14A 129.1 . . ?
C13A C14A H14A 129.1 . . ?
C16A C15A C14A 117.6(2) . . ?
C16A C15A H15A 121.2 . . ?
C14A C15A H15A 121.2 . . ?
C15A C16A S1A 114.7(2) . . ?
C15A C16A H16A 122.6 . . ?
S1A C16A H16A 122.6 . . ?
O13 Cl1 O11 112.01(18) . . ?
O13 Cl1 O12 109.30(14) . . ?
O11 Cl1 O12 109.98(12) . . ?
O13 Cl1 O14 108.27(19) . . ?
O11 Cl1 O14 108.85(13) . . ?
O12 Cl1 O14 108.34(12) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 177.41(17) . . . . ?
C10 C1 C2 C3 -2.3(3) . . . . ?
C1 C2 C3 C4 2.0(3) . . . . ?
C2 C3 C4 C5 -179.82(18) . . . . ?
C2 C3 C4 C9 1.2(3) . . . . ?
C9 C4 C5 C6 2.8(3) . . . . ?
C3 C4 C5 C6 -176.09(19) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 -1.9(3) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C7 C8 C9 C4 2.5(3) . . . . ?
C7 C8 C9 C10 -178.67(18) . . . . ?
C5 C4 C9 C8 -4.1(3) . . . . ?
C3 C4 C9 C8 174.84(17) . . . . ?
C5 C4 C9 C10 177.01(16) . . . . ?
C3 C4 C9 C10 -4.0(2) . . . . ?
O1 C1 C10 C11 -2.2(3) . . . . ?
C2 C1 C10 C11 177.47(16) . . . . ?
O1 C1 C10 C9 179.70(15) . . . . ?
C2 C1 C10 C9 -0.6(3) . . . . ?
C8 C9 C10 C11 6.9(3) . . . . ?
C4 C9 C10 C11 -174.32(16) . . . . ?
C8 C9 C10 C1 -175.06(17) . . . . ?
C4 C9 C10 C1 3.7(2) . . . . ?
C12 N1 C11 C10 -176.66(19) . . . . ?
C1 C10 C11 N1 1.3(3) . . . . ?
C9 C10 C11 N1 179.33(17) . . . . ?
C11 N1 C12 C13 163.69(18) . . . . ?
N1 C12 C13 C14 -96.5(2) . . . . ?
N1 C12 C13 S1 85.0(2) . . . . ?
C16 S1 C13 C14 0.27(15) . . . . ?
C16 S1 C13 C12 178.99(15) . . . . ?
C12 C13 C14 C15 -178.93(17) . . . . ?
S1 C13 C14 C15 -0.31(19) . . . . ?
C13 C14 C15 C16 0.2(2) . . . . ?
C14 C15 C16 S1 0.0(2) . . . . ?
C13 S1 C16 C15 -0.14(16) . . . . ?
O1A C1A C2A C3A -179.88(18) . . . . ?
C10A C1A C2A C3A 1.1(3) . . . . ?
C1A C2A C3A C4A 0.0(3) . . . . ?
C2A C3A C4A C9A -0.2(3) . . . . ?
C2A C3A C4A C5A 179.47(19) . . . . ?
C9A C4A C5A C6A -1.1(3) . . . . ?
C3A C4A C5A C6A 179.18(19) . . . . ?
C4A C5A C6A C7A 1.0(3) . . . . ?
C5A C6A C7A C8A 0.3(3) . . . . ?
C6A C7A C8A C9A -1.5(3) . . . . ?
C5A C4A C9A C8A 0.0(3) . . . . ?
C3A C4A C9A C8A 179.72(18) . . . . ?
C5A C4A C9A C10A 179.72(17) . . . . ?
C3A C4A C9A C10A -0.6(3) . . . . ?
C7A C8A C9A C4A 1.2(3) . . . . ?
C7A C8A C9A C10A -178.43(19) . . . . ?
O1A C1A C10A C11A -5.1(3) . . . . ?
C2A C1A C10A C11A 174.00(17) . . . . ?
O1A C1A C10A C9A 179.08(16) . . . . ?
C2A C1A C10A C9A -1.8(3) . . . . ?
C4A C9A C10A C11A -174.27(17) . . . . ?
C8A C9A C10A C11A 5.4(3) . . . . ?
C4A C9A C10A C1A 1.6(3) . . . . ?
C8A C9A C10A C1A -178.71(18) . . . . ?
C12A N1A C11A C10A -175.51(19) . . . . ?
C1A C10A C11A N1A 4.5(3) . . . . ?
C9A C10A C11A N1A -179.70(19) . . . . ?
C11A N1A C12A C13A 109.8(2) . . . . ?
N1A C12A C13A C14A 99.8(2) . . . . ?
N1A C12A C13A S1A -77.7(2) . . . . ?
C16A S1A C13A C12A 178.85(16) . . . . ?
C16A S1A C13A C14A 1.04(15) . . . . ?
C12A C13A C14A C15A -179.16(17) . . . . ?
S1A C13A C14A C15A -1.41(17) . . . . ?
C13A C14A C15A C16A 1.3(2) . . . . ?
C14A C15A C16A S1A -0.6(3) . . . . ?
C13A S1A C16A C15A -0.26(19) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.81(3) 1.93(3) 2.579(2) 137(2) .
N1A H1A O1A 0.82(3) 2.02(3) 2.630(2) 131(2) .
O1A H1O O1 1.17(4) 1.29(4) 2.4511(17) 179(3) .
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.047