# Electronic Supplementary Material (ESI) for Chemical Communications
# 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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#  fide research purposes only. It may contain copyright material 
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data_shelx
_database_code_depnum_ccdc_archive 'CCDC 913766'
#TrackingRef 'web_deposit_cif_file_0_ZhengjieHe_1354625575.3a.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 N4 O2'
_chemical_formula_weight         434.49
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'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
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                   11.699(5)
_cell_length_b                   15.495(7)
_cell_length_c                   12.654(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.201(8)
_cell_angle_gamma                90.00
_cell_volume                     2284.5(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    6375
_cell_measurement_theta_min      1.3
_cell_measurement_theta_max      26.1
_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9838
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_process_details   CrystalClear
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean 14.22
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            20084
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4030
_reflns_number_gt                3539
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'
_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^)+(0.0744P)^2^+0.3555P] 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         4030
_refine_ls_number_parameters     316
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1664
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.189
_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
O1 O 0.46548(17) 0.15825(13) 0.79856(15) 0.0394(5) Uani 1 1 d . . .
O2 O 0.30838(16) 0.12003(14) 0.87551(16) 0.0451(6) Uani 1 1 d . . .
N1 N 0.7902(2) 0.32957(15) 1.28209(19) 0.0355(6) Uani 1 1 d . . .
N2 N 0.9751(2) 0.38607(17) 1.0099(2) 0.0433(7) Uani 1 1 d . . .
N3 N 0.62665(19) 0.14919(15) 1.24068(19) 0.0340(6) Uani 1 1 d . . .
N4 N 0.6716(2) 0.02728(16) 0.94827(19) 0.0380(6) Uani 1 1 d . . .
C1 C 0.6267(2) 0.48578(17) 1.1541(2) 0.0283(6) Uani 1 1 d . . .
H1A H 0.5834 0.4434 1.1873 0.034 Uiso 1 1 calc R . .
C2 C 0.6325(2) 0.56909(17) 1.1935(2) 0.0326(7) Uani 1 1 d . . .
H2A H 0.5933 0.5833 1.2536 0.039 Uiso 1 1 calc R . .
C3 C 0.6945(2) 0.63150(18) 1.1466(2) 0.0353(7) Uani 1 1 d . . .
H3A H 0.6986 0.6884 1.1748 0.042 Uiso 1 1 calc R . .
C4 C 0.7510(2) 0.61102(18) 1.0579(2) 0.0349(7) Uani 1 1 d . . .
H4A H 0.7933 0.6539 1.0245 0.042 Uiso 1 1 calc R . .
C5 C 0.7452(2) 0.52755(17) 1.0186(2) 0.0314(6) Uani 1 1 d . . .
H5A H 0.7840 0.5137 0.9580 0.038 Uiso 1 1 calc R . .
C6 C 0.6841(2) 0.46376(16) 1.06584(19) 0.0245(6) Uani 1 1 d . . .
C7 C 0.6834(2) 0.37218(16) 1.02353(19) 0.0239(6) Uani 1 1 d . . .
H7A H 0.6917 0.3758 0.9457 0.029 Uiso 1 1 calc R . .
C8 C 0.7883(2) 0.31884(17) 1.07523(19) 0.0248(6) Uani 1 1 d . . .
C9 C 0.7874(2) 0.22240(16) 1.03604(19) 0.0244(6) Uani 1 1 d . . .
H9A H 0.7958 0.2264 0.9582 0.029 Uiso 1 1 calc R . .
C10 C 0.6683(2) 0.17770(16) 1.04340(19) 0.0236(6) Uani 1 1 d . . .
C11 C 0.5703(2) 0.23466(16) 0.98564(19) 0.0246(6) Uani 1 1 d . A .
H11A H 0.5893 0.2428 0.9108 0.030 Uiso 1 1 calc R . .
C12 C 0.5719(2) 0.32354(16) 1.0371(2) 0.0241(6) Uani 1 1 d . . .
H12A H 0.5628 0.3171 1.1138 0.029 Uiso 1 1 calc R . .
H12B H 0.5062 0.3577 1.0051 0.029 Uiso 1 1 calc R . .
C13 C 0.7913(2) 0.32466(17) 1.1919(2) 0.0262(6) Uani 1 1 d . . .
C14 C 0.8955(2) 0.35703(18) 1.0419(2) 0.0298(6) Uani 1 1 d . . .
C15 C 0.8909(2) 0.16978(17) 1.0808(2) 0.0279(6) Uani 1 1 d . . .
C16 C 0.9111(2) 0.14662(19) 1.1863(2) 0.0354(7) Uani 1 1 d . . .
H16A H 0.8585 0.1637 1.2353 0.042 Uiso 1 1 calc R . .
C17 C 1.0073(3) 0.0987(2) 1.2217(2) 0.0421(8) Uani 1 1 d . . .
H17A H 1.0200 0.0835 1.2946 0.051 Uiso 1 1 calc R . .
C18 C 1.0846(2) 0.0730(2) 1.1519(2) 0.0417(8) Uani 1 1 d . . .
H18A H 1.1503 0.0401 1.1762 0.050 Uiso 1 1 calc R . .
C19 C 1.0657(2) 0.0957(2) 1.0463(2) 0.0398(7) Uani 1 1 d . . .
H19A H 1.1185 0.0780 0.9978 0.048 Uiso 1 1 calc R . .
C20 C 0.9701(2) 0.14403(19) 1.0104(2) 0.0345(7) Uani 1 1 d . . .
H20A H 0.9583 0.1597 0.9376 0.041 Uiso 1 1 calc R . .
C21 C 0.6443(2) 0.16146(16) 1.1546(2) 0.0261(6) Uani 1 1 d . . .
C22 C 0.6706(2) 0.09256(18) 0.9902(2) 0.0279(6) Uani 1 1 d . . .
C23 C 0.4538(2) 0.19184(16) 0.98089(19) 0.0246(6) Uani 1 1 d . . .
C24 C 0.3880(2) 0.19179(18) 1.0608(2) 0.0298(6) Uani 1 1 d D A .
C25 C 0.4121(2) 0.15477(16) 0.8758(2) 0.0269(6) Uani 1 1 d . A .
C26 C 0.2578(3) 0.0847(2) 0.7762(3) 0.0536(9) Uani 0.684(14) 1 d PDU A 1
H26A H 0.2240 0.0274 0.7885 0.064 Uiso 0.684(14) 1 calc PR A 1
H26B H 0.3174 0.0776 0.7262 0.064 Uiso 0.684(14) 1 calc PR A 1
C27 C 0.1690(7) 0.1435(5) 0.7316(5) 0.061(2) Uani 0.684(14) 1 d PDU A 1
H27A H 0.1338 0.1200 0.6644 0.092 Uiso 0.684(14) 1 calc PR A 1
H27B H 0.2032 0.1999 0.7187 0.092 Uiso 0.684(14) 1 calc PR A 1
H27C H 0.1102 0.1502 0.7814 0.092 Uiso 0.684(14) 1 calc PR A 1
C26' C 0.2578(3) 0.0847(2) 0.7762(3) 0.0536(9) Uani 0.316(14) 1 d PDU A 2
H26C H 0.2761 0.0224 0.7741 0.064 Uiso 0.316(14) 1 calc PR A 2
H26D H 0.2936 0.1130 0.7173 0.064 Uiso 0.316(14) 1 calc PR A 2
C27' C 0.1304(8) 0.0955(14) 0.7584(12) 0.068(4) Uani 0.316(14) 1 d PDU A 2
H27D H 0.1026 0.0690 0.6906 0.101 Uiso 0.316(14) 1 calc PR A 2
H27E H 0.1114 0.1571 0.7568 0.101 Uiso 0.316(14) 1 calc PR A 2
H27F H 0.0939 0.0675 0.8161 0.101 Uiso 0.316(14) 1 calc PR A 2
H24A H 0.412(2) 0.2176(16) 1.1280(12) 0.037(8) Uiso 1 1 d D . .
H24B H 0.3151(13) 0.1620(15) 1.054(2) 0.033(7) Uiso 1 1 d 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
O1 0.0414(12) 0.0499(13) 0.0269(11) -0.0102(9) 0.0035(9) -0.0060(10)
O2 0.0323(11) 0.0614(14) 0.0407(13) -0.0149(10) -0.0010(9) -0.0131(10)
N1 0.0442(15) 0.0373(14) 0.0244(14) -0.0006(10) 0.0005(11) 0.0033(11)
N2 0.0307(14) 0.0480(16) 0.0524(17) 0.0020(13) 0.0100(12) -0.0062(12)
N3 0.0334(13) 0.0397(14) 0.0291(14) 0.0031(11) 0.0032(11) 0.0004(10)
N4 0.0429(15) 0.0340(14) 0.0374(14) -0.0026(11) 0.0051(11) 0.0029(11)
C1 0.0281(14) 0.0297(14) 0.0269(14) 0.0000(11) 0.0010(11) -0.0009(11)
C2 0.0341(15) 0.0314(15) 0.0318(16) -0.0046(12) -0.0006(12) 0.0040(12)
C3 0.0343(16) 0.0263(15) 0.0428(18) -0.0013(12) -0.0095(14) 0.0048(12)
C4 0.0313(15) 0.0289(15) 0.0439(18) 0.0085(13) 0.0004(13) -0.0012(12)
C5 0.0298(15) 0.0345(15) 0.0298(15) 0.0035(12) 0.0014(12) -0.0004(12)
C6 0.0242(13) 0.0274(14) 0.0210(13) 0.0015(10) -0.0027(10) 0.0003(11)
C7 0.0233(13) 0.0300(14) 0.0182(13) 0.0024(10) 0.0007(10) -0.0010(11)
C8 0.0225(13) 0.0317(14) 0.0204(14) -0.0015(11) 0.0021(11) -0.0029(11)
C9 0.0244(13) 0.0287(14) 0.0207(13) -0.0035(11) 0.0052(11) -0.0013(11)
C10 0.0255(13) 0.0255(13) 0.0197(13) -0.0027(10) 0.0017(11) 0.0000(11)
C11 0.0258(13) 0.0258(13) 0.0221(14) 0.0027(10) 0.0008(11) 0.0001(11)
C12 0.0214(13) 0.0278(14) 0.0226(14) 0.0005(11) -0.0001(11) 0.0011(11)
C13 0.0228(13) 0.0281(14) 0.0272(16) 0.0000(11) 0.0006(11) 0.0007(11)
C14 0.0255(14) 0.0354(15) 0.0282(15) -0.0040(12) 0.0010(12) -0.0001(12)
C15 0.0249(14) 0.0320(15) 0.0266(15) -0.0027(11) 0.0012(11) 0.0015(11)
C16 0.0311(15) 0.0430(17) 0.0320(16) -0.0008(13) 0.0023(13) 0.0100(13)
C17 0.0396(17) 0.0507(19) 0.0343(17) -0.0020(14) -0.0063(14) 0.0122(15)
C18 0.0296(15) 0.0486(19) 0.0453(19) -0.0107(14) -0.0056(14) 0.0104(14)
C19 0.0275(15) 0.0524(19) 0.0395(18) -0.0122(14) 0.0025(13) 0.0072(14)
C20 0.0296(15) 0.0438(17) 0.0301(16) -0.0071(13) 0.0017(12) 0.0038(13)
C21 0.0254(14) 0.0288(14) 0.0239(15) 0.0027(11) 0.0011(11) 0.0015(11)
C22 0.0262(14) 0.0316(15) 0.0261(15) 0.0001(12) 0.0029(11) 0.0006(11)
C23 0.0262(13) 0.0239(13) 0.0231(14) 0.0018(10) -0.0010(11) 0.0003(11)
C24 0.0319(15) 0.0297(15) 0.0277(16) 0.0016(12) 0.0032(13) -0.0024(12)
C25 0.0243(13) 0.0245(13) 0.0311(16) -0.0001(11) -0.0017(12) 0.0020(11)
C26 0.0442(18) 0.065(2) 0.049(2) -0.0240(17) -0.0107(16) -0.0099(17)
C27 0.067(4) 0.072(4) 0.040(3) -0.014(3) -0.017(3) 0.011(3)
C26' 0.0442(18) 0.065(2) 0.049(2) -0.0240(17) -0.0107(16) -0.0099(17)
C27' 0.056(6) 0.090(9) 0.055(7) -0.016(6) -0.003(5) -0.017(6)
_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 C25 1.208(3) . ?
O2 C25 1.327(3) . ?
O2 C26 1.446(3) . ?
N1 C13 1.145(3) . ?
N2 C14 1.141(3) . ?
N3 C21 1.143(3) . ?
N4 C22 1.143(3) . ?
C1 C2 1.383(4) . ?
C1 C6 1.397(4) . ?
C1 H1A 0.9500 . ?
C2 C3 1.375(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.391(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.385(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.387(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.516(3) . ?
C7 C12 1.530(3) . ?
C7 C8 1.572(3) . ?
C7 H7A 1.0000 . ?
C8 C13 1.477(4) . ?
C8 C14 1.483(4) . ?
C8 C9 1.574(3) . ?
C9 C15 1.525(4) . ?
C9 C10 1.566(3) . ?
C9 H9A 1.0000 . ?
C10 C21 1.481(4) . ?
C10 C22 1.482(4) . ?
C10 C11 1.574(3) . ?
C11 C23 1.512(3) . ?
C11 C12 1.523(3) . ?
C11 H11A 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C15 C16 1.383(4) . ?
C15 C20 1.400(4) . ?
C16 C17 1.388(4) . ?
C16 H16A 0.9500 . ?
C17 C18 1.380(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.379(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.388(4) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?
C23 C24 1.325(4) . ?
C23 C25 1.489(4) . ?
C24 H24A 0.959(10) . ?
C24 H24B 0.967(10) . ?
C26 C27 1.457(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C27' H27D 0.9800 . ?
C27' H27E 0.9800 . ?
C27' H27F 0.9800 . ?
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
C25 O2 C26 117.3(2) . . ?
C2 C1 C6 120.3(2) . . ?
C2 C1 H1A 119.9 . . ?
C6 C1 H1A 119.9 . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 C7 120.1(2) . . ?
C1 C6 C7 121.6(2) . . ?
C6 C7 C12 113.5(2) . . ?
C6 C7 C8 111.5(2) . . ?
C12 C7 C8 109.6(2) . . ?
C6 C7 H7A 107.3 . . ?
C12 C7 H7A 107.3 . . ?
C8 C7 H7A 107.3 . . ?
C13 C8 C14 108.4(2) . . ?
C13 C8 C7 109.3(2) . . ?
C14 C8 C7 108.7(2) . . ?
C13 C8 C9 111.8(2) . . ?
C14 C8 C9 105.7(2) . . ?
C7 C8 C9 112.7(2) . . ?
C15 C9 C10 115.0(2) . . ?
C15 C9 C8 114.1(2) . . ?
C10 C9 C8 112.40(19) . . ?
C15 C9 H9A 104.7 . . ?
C10 C9 H9A 104.7 . . ?
C8 C9 H9A 104.7 . . ?
C21 C10 C22 107.0(2) . . ?
C21 C10 C9 112.2(2) . . ?
C22 C10 C9 108.28(19) . . ?
C21 C10 C11 110.1(2) . . ?
C22 C10 C11 109.3(2) . . ?
C9 C10 C11 109.8(2) . . ?
C23 C11 C12 113.0(2) . . ?
C23 C11 C10 112.9(2) . . ?
C12 C11 C10 109.1(2) . . ?
C23 C11 H11A 107.2 . . ?
C12 C11 H11A 107.2 . . ?
C10 C11 H11A 107.2 . . ?
C11 C12 C7 112.0(2) . . ?
C11 C12 H12A 109.2 . . ?
C7 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C7 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N1 C13 C8 178.0(3) . . ?
N2 C14 C8 175.8(3) . . ?
C16 C15 C20 118.4(2) . . ?
C16 C15 C9 123.9(2) . . ?
C20 C15 C9 117.7(2) . . ?
C15 C16 C17 120.9(3) . . ?
C15 C16 H16A 119.5 . . ?
C17 C16 H16A 119.5 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C19 C18 C17 119.3(3) . . ?
C19 C18 H18A 120.3 . . ?
C17 C18 H18A 120.3 . . ?
C18 C19 C20 120.6(3) . . ?
C18 C19 H19A 119.7 . . ?
C20 C19 H19A 119.7 . . ?
C19 C20 C15 120.3(3) . . ?
C19 C20 H20A 119.8 . . ?
C15 C20 H20A 119.8 . . ?
N3 C21 C10 179.5(3) . . ?
N4 C22 C10 179.2(3) . . ?
C24 C23 C25 121.0(2) . . ?
C24 C23 C11 123.6(2) . . ?
C25 C23 C11 115.2(2) . . ?
C23 C24 H24A 121.9(17) . . ?
C23 C24 H24B 119.8(16) . . ?
H24A C24 H24B 118(2) . . ?
O1 C25 O2 123.7(2) . . ?
O1 C25 C23 123.6(2) . . ?
O2 C25 C23 112.7(2) . . ?
O2 C26 C27 108.8(3) . . ?
O2 C26 H26A 109.9 . . ?
C27 C26 H26A 109.9 . . ?
O2 C26 H26B 109.9 . . ?
C27 C26 H26B 109.9 . . ?
H26A C26 H26B 108.3 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
H27D C27' H27E 109.5 . . ?
H27D C27' H27F 109.5 . . ?
H27E C27' H27F 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
C6 C1 C2 C3 0.1(4) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C4 C5 C6 C7 -177.5(2) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
C2 C1 C6 C7 177.4(2) . . . . ?
C5 C6 C7 C12 -148.7(2) . . . . ?
C1 C6 C7 C12 33.1(3) . . . . ?
C5 C6 C7 C8 86.9(3) . . . . ?
C1 C6 C7 C8 -91.3(3) . . . . ?
C6 C7 C8 C13 52.8(3) . . . . ?
C12 C7 C8 C13 -73.7(2) . . . . ?
C6 C7 C8 C14 -65.4(3) . . . . ?
C12 C7 C8 C14 168.2(2) . . . . ?
C6 C7 C8 C9 177.85(19) . . . . ?
C12 C7 C8 C9 51.4(3) . . . . ?
C13 C8 C9 C15 -59.0(3) . . . . ?
C14 C8 C9 C15 58.8(3) . . . . ?
C7 C8 C9 C15 177.4(2) . . . . ?
C13 C8 C9 C10 74.2(3) . . . . ?
C14 C8 C9 C10 -168.0(2) . . . . ?
C7 C8 C9 C10 -49.4(3) . . . . ?
C15 C9 C10 C21 62.3(3) . . . . ?
C8 C9 C10 C21 -70.5(3) . . . . ?
C15 C9 C10 C22 -55.6(3) . . . . ?
C8 C9 C10 C22 171.6(2) . . . . ?
C15 C9 C10 C11 -174.9(2) . . . . ?
C8 C9 C10 C11 52.3(3) . . . . ?
C21 C10 C11 C23 -61.1(3) . . . . ?
C22 C10 C11 C23 56.2(3) . . . . ?
C9 C10 C11 C23 174.85(19) . . . . ?
C21 C10 C11 C12 65.4(3) . . . . ?
C22 C10 C11 C12 -177.29(19) . . . . ?
C9 C10 C11 C12 -58.6(2) . . . . ?
C23 C11 C12 C7 -169.8(2) . . . . ?
C10 C11 C12 C7 63.7(3) . . . . ?
C6 C7 C12 C11 175.2(2) . . . . ?
C8 C7 C12 C11 -59.4(3) . . . . ?
C14 C8 C13 N1 145(8) . . . . ?
C7 C8 C13 N1 26(8) . . . . ?
C9 C8 C13 N1 -99(8) . . . . ?
C13 C8 C14 N2 -171(4) . . . . ?
C7 C8 C14 N2 -52(4) . . . . ?
C9 C8 C14 N2 69(4) . . . . ?
C10 C9 C15 C16 -63.8(3) . . . . ?
C8 C9 C15 C16 68.2(3) . . . . ?
C10 C9 C15 C20 116.6(3) . . . . ?
C8 C9 C15 C20 -111.4(3) . . . . ?
C20 C15 C16 C17 -0.3(4) . . . . ?
C9 C15 C16 C17 -179.9(3) . . . . ?
C15 C16 C17 C18 -0.2(5) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C17 C18 C19 C20 0.2(5) . . . . ?
C18 C19 C20 C15 -0.6(5) . . . . ?
C16 C15 C20 C19 0.7(4) . . . . ?
C9 C15 C20 C19 -179.7(3) . . . . ?
C22 C10 C21 N3 116(33) . . . . ?
C9 C10 C21 N3 -2(33) . . . . ?
C11 C10 C21 N3 -125(33) . . . . ?
C21 C10 C22 N4 130(24) . . . . ?
C9 C10 C22 N4 -109(24) . . . . ?
C11 C10 C22 N4 11(24) . . . . ?
C12 C11 C23 C24 -43.5(3) . . . . ?
C10 C11 C23 C24 81.0(3) . . . . ?
C12 C11 C23 C25 131.8(2) . . . . ?
C10 C11 C23 C25 -103.8(2) . . . . ?
C26 O2 C25 O1 -0.1(4) . . . . ?
C26 O2 C25 C23 177.9(2) . . . . ?
C24 C23 C25 O1 174.9(3) . . . . ?
C11 C23 C25 O1 -0.4(4) . . . . ?
C24 C23 C25 O2 -3.0(4) . . . . ?
C11 C23 C25 O2 -178.4(2) . . . . ?
C25 O2 C26 C27 -105.1(5) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.050


data_r120531a1
_database_code_depnum_ccdc_archive 'CCDC 913769'
#TrackingRef 'web_deposit_cif_file_0_ZhengjieHe_1354625738.5a.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 N O5 S'
_chemical_formula_weight         423.47
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   7.8575(16)
_cell_length_b                   8.2529(17)
_cell_length_c                   17.024(3)
_cell_angle_alpha                100.47(3)
_cell_angle_beta                 92.60(3)
_cell_angle_gamma                108.88(3)
_cell_volume                     1020.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2992
_cell_measurement_theta_min      2.6666
_cell_measurement_theta_max      27.9024
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9622
_exptl_absorpt_correction_T_max  0.9733
_exptl_absorpt_process_details   crystalclear
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10574
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0935
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         27.91
_reflns_number_total             4800
_reflns_number_gt                2613
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_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^)+(0.0400P)^2^+0.0000P] 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       0.080(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4800
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_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 0.83680(6) 0.83813(6) 0.29948(3) 0.04138(17) Uani 1 1 d . . .
O1 O 0.48618(18) 0.3458(2) 0.05068(9) 0.0702(5) Uani 1 1 d . . .
O2 O 0.09673(15) 0.45595(16) 0.17340(8) 0.0452(4) Uani 1 1 d . . .
O3 O 0.3447(2) 1.05382(18) 0.37638(9) 0.0595(4) Uani 1 1 d . . .
O4 O 0.86265(18) 1.00614(16) 0.34763(9) 0.0557(4) Uani 1 1 d . . .
O5 O 0.95705(16) 0.81434(16) 0.24144(8) 0.0488(4) Uani 1 1 d . . .
N1 N 0.63296(18) 0.77521(19) 0.24786(9) 0.0389(4) Uani 1 1 d . . .
C1 C 0.3720(2) 0.4028(2) 0.07973(11) 0.0437(5) Uani 1 1 d . . .
C2 C 0.1788(2) 0.3267(2) 0.04822(11) 0.0374(4) Uani 1 1 d . . .
C3 C 0.1205(3) 0.2197(3) -0.02796(12) 0.0492(5) Uani 1 1 d . . .
H3 H 0.2053 0.1975 -0.0608 0.059 Uiso 1 1 calc R . .
C4 C -0.0603(3) 0.1466(3) -0.05514(13) 0.0567(6) Uani 1 1 d . . .
H4 H -0.0980 0.0762 -0.1063 0.068 Uiso 1 1 calc R . .
C5 C -0.1860(3) 0.1783(3) -0.00591(13) 0.0578(6) Uani 1 1 d . . .
H5 H -0.3087 0.1281 -0.0240 0.069 Uiso 1 1 calc R . .
C6 C -0.1322(3) 0.2826(3) 0.06902(13) 0.0518(5) Uani 1 1 d . . .
H6 H -0.2181 0.3029 0.1017 0.062 Uiso 1 1 calc R . .
C7 C 0.0492(2) 0.3576(2) 0.09627(11) 0.0391(5) Uani 1 1 d . . .
C8 C 0.2622(2) 0.6024(2) 0.18293(11) 0.0354(4) Uani 1 1 d . . .
H8 H 0.2428 0.6904 0.1553 0.042 Uiso 1 1 calc R . .
C9 C 0.3118(2) 0.6799(2) 0.27162(10) 0.0363(4) Uani 1 1 d . . .
H9A H 0.3227 0.5906 0.2996 0.044 Uiso 1 1 calc R . .
H9B H 0.2167 0.7203 0.2927 0.044 Uiso 1 1 calc R . .
C10 C 0.4906(2) 0.8329(2) 0.28668(11) 0.0355(4) Uani 1 1 d . . .
H10 H 0.5270 0.8681 0.3448 0.043 Uiso 1 1 calc R . .
C11 C 0.5836(2) 0.6330(2) 0.18382(11) 0.0382(5) Uani 1 1 d . . .
H11 H 0.6744 0.5944 0.1631 0.046 Uiso 1 1 calc R . .
C12 C 0.4140(2) 0.5481(2) 0.14996(10) 0.0348(4) Uani 1 1 d . . .
C13 C 0.5324(3) 1.0378(3) 0.19176(13) 0.0567(6) Uani 1 1 d . . .
H13A H 0.5162 1.1355 0.1771 0.068 Uiso 1 1 calc R . .
H13B H 0.5929 0.9751 0.1602 0.068 Uiso 1 1 calc R . .
C14 C 0.4696(2) 0.9883(2) 0.25743(11) 0.0367(4) Uani 1 1 d . . .
C15 C 0.3718(2) 1.0843(2) 0.31012(13) 0.0431(5) Uani 1 1 d . . .
C16 C 0.3096(3) 1.2197(3) 0.28120(14) 0.0640(7) Uani 1 1 d . . .
H16A H 0.2302 1.2530 0.3170 0.096 Uiso 1 1 calc R . .
H16B H 0.2463 1.1719 0.2281 0.096 Uiso 1 1 calc R . .
H16C H 0.4127 1.3207 0.2800 0.096 Uiso 1 1 calc R . .
C17 C 0.8170(2) 0.6871(2) 0.36150(11) 0.0358(4) Uani 1 1 d . . .
C18 C 0.8376(2) 0.5282(2) 0.33106(11) 0.0393(5) Uani 1 1 d . . .
H18 H 0.8689 0.5048 0.2792 0.047 Uiso 1 1 calc R . .
C19 C 0.8115(2) 0.4049(2) 0.37830(12) 0.0441(5) Uani 1 1 d . . .
H19 H 0.8260 0.2984 0.3578 0.053 Uiso 1 1 calc R . .
C20 C 0.7640(3) 0.4357(3) 0.45554(12) 0.0491(5) Uani 1 1 d . . .
C21 C 0.7464(3) 0.5957(3) 0.48422(13) 0.0599(6) Uani 1 1 d . . .
H21 H 0.7162 0.6196 0.5362 0.072 Uiso 1 1 calc R . .
C22 C 0.7720(3) 0.7216(3) 0.43873(13) 0.0533(6) Uani 1 1 d . . .
H22 H 0.7591 0.8286 0.4597 0.064 Uiso 1 1 calc R . .
C23 C 0.7340(3) 0.2990(3) 0.50562(13) 0.0713(7) Uani 1 1 d . . .
H23A H 0.7667 0.2029 0.4781 0.107 Uiso 1 1 d R . .
H23B H 0.6088 0.2578 0.5144 0.107 Uiso 1 1 d R . .
H23C H 0.8076 0.3488 0.5564 0.107 Uiso 1 1 d 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 0.0299(2) 0.0397(3) 0.0565(4) 0.0113(3) 0.0023(2) 0.0140(2)
O1 0.0454(8) 0.0887(11) 0.0737(11) -0.0152(9) 0.0084(8) 0.0359(8)
O2 0.0340(7) 0.0477(8) 0.0493(9) 0.0053(7) 0.0141(6) 0.0090(6)
O3 0.0749(11) 0.0622(10) 0.0518(9) 0.0092(8) 0.0155(8) 0.0374(8)
O4 0.0482(8) 0.0317(8) 0.0815(11) -0.0008(8) -0.0058(8) 0.0143(6)
O5 0.0322(7) 0.0597(9) 0.0619(9) 0.0225(7) 0.0132(6) 0.0192(6)
N1 0.0294(8) 0.0440(10) 0.0460(10) 0.0048(8) 0.0014(7) 0.0190(7)
C1 0.0366(10) 0.0527(13) 0.0474(12) 0.0113(11) 0.0089(9) 0.0216(9)
C2 0.0372(9) 0.0382(11) 0.0410(11) 0.0109(9) 0.0060(8) 0.0167(8)
C3 0.0530(12) 0.0546(13) 0.0412(12) 0.0088(11) 0.0055(10) 0.0205(11)
C4 0.0608(14) 0.0599(14) 0.0436(13) 0.0085(11) -0.0039(11) 0.0152(12)
C5 0.0405(11) 0.0648(15) 0.0623(15) 0.0125(13) -0.0043(11) 0.0116(11)
C6 0.0361(10) 0.0581(13) 0.0591(14) 0.0080(12) 0.0079(10) 0.0151(10)
C7 0.0373(10) 0.0394(11) 0.0426(12) 0.0093(10) 0.0058(9) 0.0152(9)
C8 0.0305(9) 0.0334(10) 0.0446(11) 0.0114(9) 0.0084(8) 0.0117(8)
C9 0.0363(9) 0.0368(10) 0.0424(11) 0.0134(9) 0.0110(8) 0.0177(8)
C10 0.0344(9) 0.0372(11) 0.0401(11) 0.0094(9) 0.0066(8) 0.0180(8)
C11 0.0333(9) 0.0435(12) 0.0460(12) 0.0131(10) 0.0099(9) 0.0212(8)
C12 0.0327(9) 0.0404(11) 0.0376(11) 0.0111(9) 0.0081(8) 0.0186(8)
C13 0.0648(14) 0.0518(13) 0.0687(15) 0.0280(12) 0.0213(12) 0.0299(11)
C14 0.0309(9) 0.0332(10) 0.0471(12) 0.0096(9) 0.0020(8) 0.0118(8)
C15 0.0385(10) 0.0324(11) 0.0549(13) 0.0025(10) -0.0003(10) 0.0117(8)
C16 0.0721(15) 0.0475(13) 0.0879(18) 0.0195(13) 0.0150(13) 0.0371(12)
C17 0.0301(9) 0.0394(11) 0.0389(11) 0.0038(9) 0.0019(8) 0.0159(8)
C18 0.0389(10) 0.0407(11) 0.0381(11) 0.0048(9) 0.0047(8) 0.0149(9)
C19 0.0479(11) 0.0366(11) 0.0466(12) 0.0080(10) -0.0002(9) 0.0139(9)
C20 0.0439(11) 0.0588(14) 0.0437(13) 0.0159(11) 0.0007(9) 0.0139(10)
C21 0.0723(15) 0.0763(17) 0.0366(12) 0.0111(12) 0.0107(11) 0.0320(13)
C22 0.0612(14) 0.0547(14) 0.0474(13) -0.0005(12) 0.0051(11) 0.0303(11)
C23 0.0738(16) 0.0848(18) 0.0581(15) 0.0367(14) 0.0065(12) 0.0188(14)
_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 O4 1.4231(14) . ?
S1 O5 1.4289(13) . ?
S1 N1 1.6659(16) . ?
S1 C17 1.7496(19) . ?
O1 C1 1.2243(19) . ?
O2 C7 1.376(2) . ?
O2 C8 1.439(2) . ?
O3 C15 1.213(2) . ?
N1 C11 1.385(2) . ?
N1 C10 1.4874(19) . ?
C1 C12 1.471(3) . ?
C1 C2 1.475(2) . ?
C2 C7 1.392(2) . ?
C2 C3 1.393(3) . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(3) . ?
C6 H6 0.9300 . ?
C8 C12 1.501(2) . ?
C8 C9 1.508(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.528(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C14 1.510(2) . ?
C10 H10 0.9800 . ?
C11 C12 1.334(2) . ?
C11 H11 0.9300 . ?
C13 C14 1.322(2) . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
C14 C15 1.490(2) . ?
C15 C16 1.504(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C22 1.381(3) . ?
C17 C18 1.382(2) . ?
C18 C19 1.380(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(3) . ?
C20 C23 1.500(3) . ?
C21 C22 1.375(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
O4 S1 O5 121.05(9) . . ?
O4 S1 N1 105.82(8) . . ?
O5 S1 N1 105.73(8) . . ?
O4 S1 C17 109.40(9) . . ?
O5 S1 C17 108.97(8) . . ?
N1 S1 C17 104.54(9) . . ?
C7 O2 C8 113.81(13) . . ?
C11 N1 C10 119.63(14) . . ?
C11 N1 S1 119.33(12) . . ?
C10 N1 S1 118.04(12) . . ?
O1 C1 C12 123.30(17) . . ?
O1 C1 C2 122.31(18) . . ?
C12 C1 C2 114.36(15) . . ?
C7 C2 C3 118.49(18) . . ?
C7 C2 C1 119.65(17) . . ?
C3 C2 C1 121.84(17) . . ?
C4 C3 C2 120.79(19) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 119.95(19) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
O2 C7 C6 117.89(17) . . ?
O2 C7 C2 121.53(16) . . ?
C6 C7 C2 120.50(19) . . ?
O2 C8 C12 111.77(14) . . ?
O2 C8 C9 107.74(14) . . ?
C12 C8 C9 109.14(15) . . ?
O2 C8 H8 109.4 . . ?
C12 C8 H8 109.4 . . ?
C9 C8 H8 109.4 . . ?
C8 C9 C10 110.72(14) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N1 C10 C14 111.51(14) . . ?
N1 C10 C9 109.61(14) . . ?
C14 C10 C9 111.17(14) . . ?
N1 C10 H10 108.1 . . ?
C14 C10 H10 108.1 . . ?
C9 C10 H10 108.1 . . ?
C12 C11 N1 124.12(16) . . ?
C12 C11 H11 117.9 . . ?
N1 C11 H11 117.9 . . ?
C11 C12 C1 121.28(16) . . ?
C11 C12 C8 119.83(17) . . ?
C1 C12 C8 118.89(16) . . ?
C14 C13 H13A 120.0 . . ?
C14 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C13 C14 C15 122.12(18) . . ?
C13 C14 C10 124.06(17) . . ?
C15 C14 C10 113.81(16) . . ?
O3 C15 C14 119.70(17) . . ?
O3 C15 C16 120.50(17) . . ?
C14 C15 C16 119.80(18) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 120.01(19) . . ?
C22 C17 S1 120.60(15) . . ?
C18 C17 S1 119.31(14) . . ?
C19 C18 C17 119.39(17) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 121.62(18) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C21 C20 C19 117.5(2) . . ?
C21 C20 C23 121.7(2) . . ?
C19 C20 C23 120.8(2) . . ?
C20 C21 C22 122.3(2) . . ?
C20 C21 H21 118.8 . . ?
C22 C21 H21 118.8 . . ?
C21 C22 C17 119.18(18) . . ?
C21 C22 H22 120.4 . . ?
C17 C22 H22 120.4 . . ?
C20 C23 H23A 109.4 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O4 S1 N1 C11 167.05(13) . . . . ?
O5 S1 N1 C11 37.50(16) . . . . ?
C17 S1 N1 C11 -77.47(15) . . . . ?
O4 S1 N1 C10 -32.59(15) . . . . ?
O5 S1 N1 C10 -162.14(12) . . . . ?
C17 S1 N1 C10 82.89(14) . . . . ?
O1 C1 C2 C7 160.36(18) . . . . ?
C12 C1 C2 C7 -17.9(3) . . . . ?
O1 C1 C2 C3 -17.7(3) . . . . ?
C12 C1 C2 C3 164.06(17) . . . . ?
C7 C2 C3 C4 0.1(3) . . . . ?
C1 C2 C3 C4 178.23(19) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C8 O2 C7 C6 -145.96(17) . . . . ?
C8 O2 C7 C2 37.3(2) . . . . ?
C5 C6 C7 O2 -177.43(17) . . . . ?
C5 C6 C7 C2 -0.6(3) . . . . ?
C3 C2 C7 O2 177.20(17) . . . . ?
C1 C2 C7 O2 -0.9(3) . . . . ?
C3 C2 C7 C6 0.5(3) . . . . ?
C1 C2 C7 C6 -177.63(18) . . . . ?
C7 O2 C8 C12 -51.4(2) . . . . ?
C7 O2 C8 C9 -171.30(14) . . . . ?
O2 C8 C9 C10 178.01(12) . . . . ?
C12 C8 C9 C10 56.48(19) . . . . ?
C11 N1 C10 C14 -99.85(18) . . . . ?
S1 N1 C10 C14 99.85(16) . . . . ?
C11 N1 C10 C9 23.7(2) . . . . ?
S1 N1 C10 C9 -136.61(14) . . . . ?
C8 C9 C10 N1 -54.03(19) . . . . ?
C8 C9 C10 C14 69.71(18) . . . . ?
C10 N1 C11 C12 4.6(3) . . . . ?
S1 N1 C11 C12 164.60(15) . . . . ?
N1 C11 C12 C1 177.25(16) . . . . ?
N1 C11 C12 C8 -1.8(3) . . . . ?
O1 C1 C12 C11 3.6(3) . . . . ?
C2 C1 C12 C11 -178.22(17) . . . . ?
O1 C1 C12 C8 -177.32(18) . . . . ?
C2 C1 C12 C8 0.9(2) . . . . ?
O2 C8 C12 C11 -148.09(17) . . . . ?
C9 C8 C12 C11 -29.0(2) . . . . ?
O2 C8 C12 C1 32.8(2) . . . . ?
C9 C8 C12 C1 151.86(16) . . . . ?
N1 C10 C14 C13 16.6(3) . . . . ?
C9 C10 C14 C13 -106.0(2) . . . . ?
N1 C10 C14 C15 -162.82(15) . . . . ?
C9 C10 C14 C15 74.5(2) . . . . ?
C13 C14 C15 O3 -167.11(19) . . . . ?
C10 C14 C15 O3 12.4(3) . . . . ?
C13 C14 C15 C16 12.1(3) . . . . ?
C10 C14 C15 C16 -168.42(17) . . . . ?
O4 S1 C17 C22 19.87(18) . . . . ?
O5 S1 C17 C22 154.25(15) . . . . ?
N1 S1 C17 C22 -93.09(17) . . . . ?
O4 S1 C17 C18 -163.47(13) . . . . ?
O5 S1 C17 C18 -29.09(16) . . . . ?
N1 S1 C17 C18 83.57(15) . . . . ?
C22 C17 C18 C19 0.5(3) . . . . ?
S1 C17 C18 C19 -176.17(14) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 C21 -1.0(3) . . . . ?
C18 C19 C20 C23 179.28(18) . . . . ?
C19 C20 C21 C22 0.8(3) . . . . ?
C23 C20 C21 C22 -179.4(2) . . . . ?
C20 C21 C22 C17 0.0(3) . . . . ?
C18 C17 C22 C21 -0.6(3) . . . . ?
S1 C17 C22 C21 175.99(15) . . . . ?
_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        27.91
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.048