# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 914969'
#TrackingRef 'SK_ANO2Bm_M_0m.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 N3 O2, F6 P'
_chemical_formula_sum            'C28 H20 F6 N3 O2 P'
_chemical_formula_weight         575.44
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a                   22.5075(12)
_cell_length_b                   12.6461(7)
_cell_length_c                   20.6804(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.996(3)
_cell_angle_gamma                90.00
_cell_volume                     5148.5(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1792
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      20.04
_exptl_crystal_description       Needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2352
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6328
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30726
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_sigmaI/netI    0.1364
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         30.60
_reflns_number_total             7910
_reflns_number_gt                2545
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-92 (ALTOMARE, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.1614P)^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    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7910
_refine_ls_number_parameters     349
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2625
_refine_ls_R_factor_gt           0.0963
_refine_ls_wR_factor_ref         0.3421
_refine_ls_wR_factor_gt          0.2562
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.999
_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
C1 C 0.67920(16) 0.28077(16) 0.27541(16) 0.0502(11) Uani 1 1 d G . .
C2 C 0.64561(17) 0.3362(2) 0.30614(16) 0.0625(13) Uani 1 1 d G . .
H2 H 0.6356 0.3032 0.3399 0.075 Uiso 1 1 calc R . .
C3 C 0.62706(16) 0.4410(2) 0.28648(16) 0.0604(13) Uani 1 1 d G . .
H3 H 0.6046 0.4781 0.3070 0.072 Uiso 1 1 calc R . .
C4 C 0.64209(15) 0.49041(16) 0.23610(15) 0.0446(10) Uani 1 1 d G . .
C5 C 0.67567(15) 0.4350(2) 0.20537(15) 0.0534(12) Uani 1 1 d G . .
H5 H 0.6857 0.4680 0.1717 0.064 Uiso 1 1 calc R . .
C6 C 0.69423(15) 0.3302(2) 0.22503(16) 0.0555(12) Uani 1 1 d G . .
H6 H 0.7167 0.2931 0.2045 0.067 Uiso 1 1 calc R . .
C7 C 0.6478(2) 0.6790(3) 0.2700(2) 0.0480(11) Uani 1 1 d . . .
C8 C 0.6909(3) 0.6796(4) 0.3456(2) 0.0653(14) Uani 1 1 d . . .
H8 H 0.7089 0.6174 0.3719 0.078 Uiso 1 1 calc R . .
C9 C 0.7057(3) 0.7756(4) 0.3795(3) 0.0776(18) Uani 1 1 d . . .
H9 H 0.7356 0.7791 0.4300 0.093 Uiso 1 1 calc R . .
C10 C 0.6778(3) 0.8678(4) 0.3416(3) 0.0722(15) Uani 1 1 d . . .
H10 H 0.6885 0.9314 0.3674 0.087 Uiso 1 1 calc R . .
C11 C 0.6347(3) 0.8686(4) 0.2665(2) 0.0585(13) Uani 1 1 d . . .
H11 H 0.6162 0.9311 0.2409 0.070 Uiso 1 1 calc R . .
C12 C 0.6204(2) 0.7725(3) 0.2314(2) 0.0462(11) Uani 1 1 d . . .
C13 C 0.5347(2) 0.8052(3) 0.0920(2) 0.0496(11) Uani 1 1 d . . .
H13A H 0.4933 0.8174 0.0945 0.060 Uiso 1 1 calc RD . .
H13B H 0.5228 0.7655 0.0472 0.060 Uiso 1 1 calc R . .
C14 C 0.5641(2) 0.9107(3) 0.0873(2) 0.0454(11) Uani 1 1 d . . .
C15 C 0.6118(2) 0.9117(4) 0.0616(2) 0.0473(11) Uani 1 1 d . . .
C16 C 0.6368(2) 0.8186(4) 0.0451(3) 0.0588(13) Uani 1 1 d . . .
H16 H 0.6218 0.7532 0.0521 0.071 Uiso 1 1 calc R . .
C17 C 0.6819(3) 0.8221(5) 0.0194(3) 0.0744(16) Uani 1 1 d . . .
H17 H 0.6984 0.7595 0.0105 0.089 Uiso 1 1 calc R . .
C18 C 0.7040(3) 0.9194(6) 0.0061(3) 0.0803(18) Uani 1 1 d . . .
H18 H 0.7339 0.9208 -0.0129 0.096 Uiso 1 1 calc R . .
C19 C 0.6825(3) 1.0093(5) 0.0204(3) 0.0717(16) Uani 1 1 d . . .
H19 H 0.6979 1.0729 0.0114 0.086 Uiso 1 1 calc R . .
C20 C 0.6360(2) 1.0112(4) 0.0495(2) 0.0555(12) Uani 1 1 d . . .
C21 C 0.6123(2) 1.1044(4) 0.0640(2) 0.0575(13) Uani 1 1 d . . .
H21 H 0.6274 1.1686 0.0555 0.069 Uiso 1 1 calc R . .
C22 C 0.5670(2) 1.1044(4) 0.0908(2) 0.0556(13) Uani 1 1 d . . .
C23 C 0.5435(3) 1.2015(4) 0.1058(3) 0.0695(15) Uani 1 1 d . . .
H23 H 0.5588 1.2652 0.0968 0.083 Uiso 1 1 calc R . .
C24 C 0.4995(3) 1.2029(5) 0.1325(3) 0.0788(17) Uani 1 1 d . . .
H24 H 0.4853 1.2672 0.1422 0.095 Uiso 1 1 calc R . .
C25 C 0.4752(3) 1.1087(5) 0.1459(3) 0.0779(17) Uani 1 1 d . . .
H25 H 0.4449 1.1107 0.1645 0.094 Uiso 1 1 calc R . .
C26 C 0.4949(2) 1.0157(3) 0.1323(2) 0.0655(14) Uani 1 1 d . . .
H26 H 0.4779 0.9541 0.1418 0.079 Uiso 1 1 calc RD . .
C27 C 0.5416(2) 1.0068(4) 0.1037(2) 0.0487(11) Uani 1 1 d . . .
C28 C 0.5865(2) 0.6379(3) 0.1522(2) 0.0456(10) Uani 1 1 d . . .
H28 H 0.5654 0.5990 0.1086 0.055 Uiso 1 1 calc R . .
N1 N 0.6976(3) 0.1740(4) 0.2950(3) 0.0780(14) Uani 1 1 d . . .
N2 N 0.62576(18) 0.5969(2) 0.21912(19) 0.0447(9) Uani 1 1 d . . .
N3 N 0.58163(17) 0.7411(3) 0.15647(17) 0.0443(9) Uani 1 1 d . . .
O1 O 0.7333(3) 0.1314(4) 0.2751(3) 0.139(2) Uani 1 1 d . . .
O2 O 0.6766(3) 0.1296(3) 0.3309(3) 0.1206(18) Uani 1 1 d . . .
F1 F 0.4662(3) 0.4663(5) 0.0553(5) 0.226(4) Uani 1 1 d . . .
F2 F 0.3649(4) 0.4641(4) -0.0409(2) 0.181(3) Uani 1 1 d . . .
F3 F 0.3789(2) 0.4326(4) 0.0666(2) 0.1399(17) Uani 1 1 d . . .
F4 F 0.3351(2) 0.5790(4) 0.0173(4) 0.203(3) Uani 1 1 d . . .
F5 F 0.4290(4) 0.6087(4) 0.0010(3) 0.182(2) Uani 1 1 d . . .
F6 F 0.4364(3) 0.5850(5) 0.1055(3) 0.197(3) Uani 1 1 d . . .
P1 P 0.39968(7) 0.52577(12) 0.03124(8) 0.0655(5) 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
C1 0.060(3) 0.034(3) 0.053(3) 0.005(2) 0.025(2) 0.003(2)
C2 0.096(4) 0.040(3) 0.067(3) 0.013(2) 0.052(3) 0.004(3)
C3 0.091(4) 0.041(3) 0.063(3) 0.008(2) 0.049(3) 0.008(3)
C4 0.056(3) 0.033(2) 0.044(2) 0.0027(19) 0.023(2) 0.0027(19)
C5 0.070(3) 0.039(3) 0.058(3) 0.003(2) 0.037(3) 0.000(2)
C6 0.060(3) 0.042(3) 0.070(3) 0.003(2) 0.036(3) 0.010(2)
C7 0.066(3) 0.032(2) 0.042(2) 0.0031(19) 0.024(2) -0.001(2)
C8 0.099(4) 0.044(3) 0.039(3) 0.011(2) 0.022(3) 0.009(3)
C9 0.125(5) 0.049(3) 0.038(3) 0.000(2) 0.023(3) 0.001(3)
C10 0.116(4) 0.039(3) 0.048(3) -0.002(2) 0.029(3) 0.000(3)
C11 0.086(3) 0.034(3) 0.047(3) 0.003(2) 0.025(3) 0.005(2)
C12 0.058(3) 0.035(2) 0.041(2) 0.005(2) 0.021(2) 0.003(2)
C13 0.050(2) 0.044(3) 0.041(2) 0.015(2) 0.011(2) 0.000(2)
C14 0.044(2) 0.041(3) 0.040(2) 0.0127(19) 0.0114(19) 0.0018(19)
C15 0.042(2) 0.049(3) 0.037(2) 0.010(2) 0.009(2) -0.001(2)
C16 0.055(3) 0.056(3) 0.056(3) 0.003(2) 0.020(2) 0.002(2)
C17 0.065(3) 0.090(5) 0.068(4) -0.005(3) 0.031(3) 0.006(3)
C18 0.054(3) 0.117(6) 0.070(4) -0.007(4) 0.030(3) -0.005(3)
C19 0.055(3) 0.093(5) 0.058(3) 0.006(3) 0.020(3) -0.024(3)
C20 0.046(2) 0.062(3) 0.045(3) 0.006(2) 0.011(2) -0.009(2)
C21 0.057(3) 0.051(3) 0.050(3) 0.010(2) 0.014(2) -0.015(2)
C22 0.061(3) 0.040(3) 0.039(2) 0.007(2) 0.004(2) -0.001(2)
C23 0.074(4) 0.049(3) 0.058(3) 0.002(2) 0.010(3) 0.003(3)
C24 0.083(4) 0.062(4) 0.062(3) -0.006(3) 0.012(3) 0.021(3)
C25 0.074(4) 0.079(5) 0.069(4) 0.001(3) 0.025(3) 0.028(3)
C26 0.060(3) 0.073(4) 0.057(3) 0.016(3) 0.023(3) 0.006(3)
C27 0.047(2) 0.045(3) 0.037(2) 0.0106(19) 0.007(2) 0.005(2)
C28 0.058(3) 0.034(3) 0.045(2) 0.002(2) 0.025(2) -0.002(2)
N1 0.105(4) 0.043(3) 0.095(4) 0.026(3) 0.055(3) 0.019(3)
N2 0.060(2) 0.0266(19) 0.045(2) 0.0068(15) 0.0229(18) 0.0053(16)
N3 0.053(2) 0.036(2) 0.0375(19) 0.0077(15) 0.0170(17) 0.0051(16)
O1 0.199(5) 0.074(3) 0.217(6) 0.058(4) 0.158(5) 0.074(4)
O2 0.198(5) 0.052(3) 0.169(5) 0.043(3) 0.134(5) 0.034(3)
F1 0.132(4) 0.139(5) 0.432(11) 0.048(6) 0.156(6) 0.037(3)
F2 0.336(8) 0.131(4) 0.099(3) -0.042(3) 0.124(5) -0.089(5)
F3 0.171(4) 0.160(4) 0.104(3) 0.025(3) 0.079(3) -0.043(3)
F4 0.089(3) 0.162(5) 0.318(9) -0.054(5) 0.068(4) 0.027(3)
F5 0.295(7) 0.122(4) 0.181(5) 0.014(3) 0.154(5) -0.075(4)
F6 0.177(5) 0.281(8) 0.133(4) -0.110(5) 0.075(4) -0.116(5)
P1 0.0703(9) 0.0733(11) 0.0681(9) -0.0067(7) 0.0455(8) -0.0108(7)
_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
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 N1 1.413(5) . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 N2 1.395(4) . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.385(6) . ?
C7 N2 1.387(5) . ?
C7 C12 1.392(6) . ?
C8 C9 1.361(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(6) . ?
C11 H11 0.9300 . ?
C12 N3 1.417(5) . ?
C13 N3 1.478(5) . ?
C13 C14 1.512(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.410(6) . ?
C14 C27 1.420(6) . ?
C15 C16 1.416(6) . ?
C15 C20 1.441(6) . ?
C16 C17 1.356(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.403(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.323(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.438(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.385(7) . ?
C21 C22 1.374(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.430(7) . ?
C22 C27 1.439(6) . ?
C23 C24 1.347(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.394(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.335(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.439(6) . ?
C26 H26 0.9300 . ?
C28 N3 1.317(5) . ?
C28 N2 1.334(5) . ?
C28 H28 0.9300 . ?
N1 O1 1.194(6) . ?
N1 O2 1.197(6) . ?
F1 P1 1.527(5) . ?
F2 P1 1.521(4) . ?
F3 P1 1.573(4) . ?
F4 P1 1.497(4) . ?
F5 P1 1.526(4) . ?
F6 P1 1.540(4) . ?
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
C2 C1 C6 120.0 . . ?
C2 C1 N1 120.0(3) . . ?
C6 C1 N1 120.0(3) . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 N2 120.5(2) . . ?
C3 C4 N2 119.5(2) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C8 C7 N2 131.1(4) . . ?
C8 C7 C12 121.1(4) . . ?
N2 C7 C12 107.7(4) . . ?
C9 C8 C7 116.7(4) . . ?
C9 C8 H8 121.7 . . ?
C7 C8 H8 121.7 . . ?
C8 C9 C10 122.2(5) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C11 C10 C9 121.8(5) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C12 C11 C10 116.6(4) . . ?
C12 C11 H11 121.7 . . ?
C10 C11 H11 121.7 . . ?
C11 C12 C7 121.6(4) . . ?
C11 C12 N3 133.6(4) . . ?
C7 C12 N3 104.8(4) . . ?
N3 C13 C14 113.5(3) . . ?
N3 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
N3 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C27 120.4(4) . . ?
C15 C14 C13 118.0(4) . . ?
C27 C14 C13 121.5(4) . . ?
C14 C15 C16 123.1(4) . . ?
C14 C15 C20 119.7(4) . . ?
C16 C15 C20 117.2(4) . . ?
C17 C16 C15 121.8(5) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 120.6(6) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 120.4(5) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 121.8(5) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C21 C20 C19 122.8(5) . . ?
C21 C20 C15 119.1(4) . . ?
C19 C20 C15 118.1(5) . . ?
C22 C21 C20 121.8(4) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C23 120.8(5) . . ?
C21 C22 C27 120.8(5) . . ?
C23 C22 C27 118.3(5) . . ?
C24 C23 C22 121.6(5) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C25 120.6(6) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 120.5(6) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 122.7(5) . . ?
C25 C26 H26 118.7 . . ?
C27 C26 H26 118.7 . . ?
C14 C27 C26 125.5(4) . . ?
C14 C27 C22 118.1(4) . . ?
C26 C27 C22 116.4(4) . . ?
N3 C28 N2 110.4(4) . . ?
N3 C28 H28 124.8 . . ?
N2 C28 H28 124.8 . . ?
O1 N1 O2 122.5(5) . . ?
O1 N1 C1 119.0(5) . . ?
O2 N1 C1 118.5(5) . . ?
C28 N2 C7 108.1(3) . . ?
C28 N2 C4 126.7(3) . . ?
C7 N2 C4 125.3(3) . . ?
C28 N3 C12 109.0(3) . . ?
C28 N3 C13 121.9(3) . . ?
C12 N3 C13 128.6(3) . . ?
F4 P1 F2 92.9(4) . . ?
F4 P1 F1 172.2(5) . . ?
F2 P1 F1 91.4(4) . . ?
F4 P1 F5 100.7(4) . . ?
F2 P1 F5 94.0(3) . . ?
F1 P1 F5 85.5(4) . . ?
F4 P1 F6 88.6(4) . . ?
F2 P1 F6 178.1(4) . . ?
F1 P1 F6 86.9(4) . . ?
F5 P1 F6 86.8(3) . . ?
F4 P1 F3 86.9(3) . . ?
F2 P1 F3 86.8(3) . . ?
F1 P1 F3 86.8(3) . . ?
F5 P1 F3 172.3(3) . . ?
F6 P1 F3 92.2(3) . . ?
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 0.0 . . . . ?
N1 C1 C2 C3 -179.5(4) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C2 C3 C4 N2 -177.3(3) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
N2 C4 C5 C6 177.3(3) . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
N1 C1 C6 C5 179.5(4) . . . . ?
N2 C7 C8 C9 176.2(5) . . . . ?
C12 C7 C8 C9 -1.0(8) . . . . ?
C7 C8 C9 C10 2.0(9) . . . . ?
C8 C9 C10 C11 -1.8(10) . . . . ?
C9 C10 C11 C12 0.5(9) . . . . ?
C10 C11 C12 C7 0.5(7) . . . . ?
C10 C11 C12 N3 -177.1(5) . . . . ?
C8 C7 C12 C11 -0.2(7) . . . . ?
N2 C7 C12 C11 -178.0(4) . . . . ?
C8 C7 C12 N3 177.9(4) . . . . ?
N2 C7 C12 N3 0.2(5) . . . . ?
N3 C13 C14 C15 77.0(5) . . . . ?
N3 C13 C14 C27 -106.9(4) . . . . ?
C27 C14 C15 C16 179.3(4) . . . . ?
C13 C14 C15 C16 -4.6(6) . . . . ?
C27 C14 C15 C20 -2.2(6) . . . . ?
C13 C14 C15 C20 174.0(4) . . . . ?
C14 C15 C16 C17 179.0(4) . . . . ?
C20 C15 C16 C17 0.4(7) . . . . ?
C15 C16 C17 C18 -2.0(8) . . . . ?
C16 C17 C18 C19 1.9(8) . . . . ?
C17 C18 C19 C20 -0.3(8) . . . . ?
C18 C19 C20 C21 -179.2(5) . . . . ?
C18 C19 C20 C15 -1.2(7) . . . . ?
C14 C15 C20 C21 0.6(6) . . . . ?
C16 C15 C20 C21 179.2(4) . . . . ?
C14 C15 C20 C19 -177.5(4) . . . . ?
C16 C15 C20 C19 1.1(6) . . . . ?
C19 C20 C21 C22 179.0(4) . . . . ?
C15 C20 C21 C22 1.0(6) . . . . ?
C20 C21 C22 C23 179.7(4) . . . . ?
C20 C21 C22 C27 -1.0(6) . . . . ?
C21 C22 C23 C24 -179.5(5) . . . . ?
C27 C22 C23 C24 1.2(7) . . . . ?
C22 C23 C24 C25 -0.5(8) . . . . ?
C23 C24 C25 C26 -0.1(8) . . . . ?
C24 C25 C26 C27 0.0(8) . . . . ?
C15 C14 C27 C26 -177.9(4) . . . . ?
C13 C14 C27 C26 6.0(6) . . . . ?
C15 C14 C27 C22 2.2(6) . . . . ?
C13 C14 C27 C22 -173.8(4) . . . . ?
C25 C26 C27 C14 -179.3(4) . . . . ?
C25 C26 C27 C22 0.6(7) . . . . ?
C21 C22 C27 C14 -0.6(6) . . . . ?
C23 C22 C27 C14 178.7(4) . . . . ?
C21 C22 C27 C26 179.5(4) . . . . ?
C23 C22 C27 C26 -1.2(6) . . . . ?
C2 C1 N1 O1 -171.2(5) . . . . ?
C6 C1 N1 O1 9.3(7) . . . . ?
C2 C1 N1 O2 8.9(7) . . . . ?
C6 C1 N1 O2 -170.6(5) . . . . ?
N3 C28 N2 C7 0.0(5) . . . . ?
N3 C28 N2 C4 179.6(4) . . . . ?
C8 C7 N2 C28 -177.6(5) . . . . ?
C12 C7 N2 C28 -0.1(5) . . . . ?
C8 C7 N2 C4 2.8(8) . . . . ?
C12 C7 N2 C4 -179.8(4) . . . . ?
C5 C4 N2 C28 59.8(5) . . . . ?
C3 C4 N2 C28 -122.8(4) . . . . ?
C5 C4 N2 C7 -120.6(4) . . . . ?
C3 C4 N2 C7 56.8(5) . . . . ?
N2 C28 N3 C12 0.1(5) . . . . ?
N2 C28 N3 C13 -172.6(3) . . . . ?
C11 C12 N3 C28 177.7(5) . . . . ?
C7 C12 N3 C28 -0.2(5) . . . . ?
C11 C12 N3 C13 -10.3(8) . . . . ?
C7 C12 N3 C13 171.9(4) . . . . ?
C14 C13 N3 C28 -141.2(4) . . . . ?
C14 C13 N3 C12 47.7(6) . . . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.60
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.819
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.071


data_shelxl2
_database_code_depnum_ccdc_archive 'CCDC 914970'
#TrackingRef 'sk_ano2bm_cn_0m.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H21 N3 O3'
_chemical_formula_sum            'C28 H21 N3 O3'
_chemical_formula_weight         447.48
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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                   8.718(3)
_cell_length_b                   12.036(4)
_cell_length_c                   12.296(4)
_cell_angle_alpha                65.498(16)
_cell_angle_beta                 86.432(17)
_cell_angle_gamma                78.223(15)
_cell_volume                     1149.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2827
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      21.67
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5812
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
SADABS-2008/1 - Bruker AXS area detector scaling and
absorption correction'
;
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17503
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_av_sigmaI/netI    0.0840
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         27.46
_reflns_number_total             5008
_reflns_number_gt                2623
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-92 (Altomare et al.,1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.2000P)^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    none
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.07(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         5008
_refine_ls_number_parameters     284
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.2083
_refine_ls_R_factor_gt           0.1450
_refine_ls_wR_factor_ref         0.4664
_refine_ls_wR_factor_gt          0.4332
_refine_ls_goodness_of_fit_ref   1.528
_refine_ls_restrained_S_all      1.548
_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
C1 C 0.2504(8) -0.0236(6) 1.0037(7) 0.0727(19) Uani 1 1 d . . .
C2 C 0.1769(8) 0.0698(6) 0.9069(7) 0.0709(18) Uani 1 1 d . . .
H2 H 0.1210 0.0527 0.8556 0.085 Uiso 1 1 calc R . .
C3 C 0.1831(7) 0.1900(5) 0.8826(6) 0.0626(16) Uani 1 1 d . . .
H3 H 0.1331 0.2541 0.8140 0.075 Uiso 1 1 calc R . .
C4 C 0.2638(6) 0.2181(5) 0.9599(5) 0.0500(13) Uani 1 1 d . . .
C5 C 0.3423(7) 0.1203(5) 1.0594(5) 0.0625(15) Uani 1 1 d . . .
H5 H 0.3988 0.1364 1.1112 0.075 Uiso 1 1 calc R . .
C6 C 0.3358(8) -0.0015(6) 1.0812(6) 0.079(2) Uani 1 1 d . . .
H6 H 0.3883 -0.0676 1.1474 0.095 Uiso 1 1 calc R . .
C7 C 0.1509(5) 0.4437(4) 0.8841(4) 0.0404(11) Uani 1 1 d . . .
C8 C -0.0052(5) 0.4339(5) 0.8903(4) 0.0457(12) Uani 1 1 d . . .
H8 H -0.0316 0.3557 0.9259 0.055 Uiso 1 1 calc R . .
C9 C -0.1213(6) 0.5384(5) 0.8446(5) 0.0522(14) Uani 1 1 d . . .
H9 H -0.2250 0.5297 0.8449 0.063 Uiso 1 1 calc R . .
C10 C -0.0867(6) 0.6553(5) 0.7985(5) 0.0564(14) Uani 1 1 d . . .
H10 H -0.1666 0.7255 0.7727 0.068 Uiso 1 1 calc R . .
C11 C 0.0667(6) 0.6676(5) 0.7908(4) 0.0508(13) Uani 1 1 d . . .
H11 H 0.0911 0.7465 0.7566 0.061 Uiso 1 1 calc R . .
C12 C 0.1851(5) 0.5640(4) 0.8333(4) 0.0377(11) Uani 1 1 d . . .
C13 C 0.4468(6) 0.5587(5) 0.7360(5) 0.0549(14) Uani 1 1 d . . .
H13A H 0.4902 0.4705 0.7622 0.066 Uiso 1 1 calc RD . .
H13B H 0.5330 0.6018 0.7250 0.066 Uiso 1 1 calc R . .
C14 C 0.3561(6) 0.6071(4) 0.6157(4) 0.0718(19) Uani 1 1 d D . .
C15 C 0.3202(6) 0.5211(5) 0.5767(4) 0.096(3) Uani 1 1 d GD . .
C16 C 0.3584(7) 0.3918(5) 0.6291(5) 0.119(4) Uani 1 1 d G . .
H16 H 0.4174 0.3509 0.7001 0.142 Uiso 1 1 calc RD . .
C17 C 0.3083(8) 0.3236(7) 0.5754(6) 0.181(7) Uani 1 1 d G . .
H17 H 0.3338 0.2371 0.6104 0.217 Uiso 1 1 calc R . .
C18 C 0.2201(8) 0.3848(9) 0.4693(6) 0.223(11) Uani 1 1 d G . .
H18 H 0.1866 0.3391 0.4333 0.267 Uiso 1 1 calc R . .
C19 C 0.1820(7) 0.5141(9) 0.4169(5) 0.222(11) Uani 1 1 d G . .
H19 H 0.1230 0.5550 0.3459 0.267 Uiso 1 1 calc R . .
C20 C 0.2321(7) 0.5823(7) 0.4706(5) 0.176(7) Uani 1 1 d GD . .
C21 C 0.1766(14) 0.7087(7) 0.4034(8) 0.230(12) Uani 1 1 d D . .
H21 H 0.1162 0.7398 0.3335 0.276 Uiso 1 1 calc R . .
C22 C 0.2212(9) 0.7836(8) 0.4520(5) 0.182(8) Uani 1 1 d GD . .
C23 C 0.1712(10) 0.9114(8) 0.3901(6) 0.238(12) Uani 1 1 d G . .
H23 H 0.1089 0.9427 0.3211 0.286 Uiso 1 1 calc R . .
C24 C 0.2144(12) 0.9925(5) 0.4312(8) 0.253(11) Uani 1 1 d G . .
H24 H 0.1809 1.0780 0.3898 0.304 Uiso 1 1 calc R . .
C25 C 0.3075(11) 0.9457(5) 0.5343(8) 0.206(7) Uani 1 1 d G . .
H25 H 0.3363 0.9999 0.5618 0.248 Uiso 1 1 calc R . .
C26 C 0.3575(8) 0.8179(5) 0.5962(5) 0.133(4) Uani 1 1 d G . .
H26 H 0.4198 0.7866 0.6652 0.160 Uiso 1 1 calc R . .
C27 C 0.3144(7) 0.7369(4) 0.5550(4) 0.098(3) Uani 1 1 d GD . .
C29 C 0.3932(6) 0.6256(4) 0.8956(5) 0.0489(13) Uani 1 1 d . . .
H29 H 0.3234 0.6407 0.9505 0.059 Uiso 1 1 calc R . .
N1 N 0.2452(9) -0.1542(7) 1.0316(9) 0.106(3) Uani 1 1 d . . .
N2 N 0.2710(4) 0.3392(3) 0.9367(4) 0.0462(11) Uani 1 1 d . . .
H2A H 0.3569 0.3519 0.9562 0.055 Uiso 1 1 calc R . .
N3 N 0.3441(4) 0.5785(3) 0.8269(3) 0.0407(10) Uani 1 1 d . . .
O1 O 0.3141(10) -0.2379(5) 1.1169(7) 0.145(3) Uani 1 1 d . . .
O2 O 0.1658(8) -0.1695(5) 0.9581(8) 0.137(3) Uani 1 1 d . . .
O3 O 0.5236(4) 0.6509(4) 0.8926(4) 0.0639(12) 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
C1 0.077(4) 0.056(4) 0.104(5) -0.046(4) 0.037(4) -0.035(3)
C2 0.069(4) 0.061(4) 0.104(5) -0.051(4) 0.011(4) -0.024(3)
C3 0.069(4) 0.055(3) 0.078(4) -0.039(3) 0.000(3) -0.017(3)
C4 0.049(3) 0.041(3) 0.064(3) -0.025(2) 0.006(2) -0.011(2)
C5 0.065(4) 0.046(3) 0.070(4) -0.018(3) 0.004(3) -0.009(3)
C6 0.087(5) 0.045(3) 0.075(4) -0.006(3) 0.023(4) 0.005(3)
C7 0.041(3) 0.042(3) 0.041(3) -0.020(2) -0.002(2) -0.009(2)
C8 0.043(3) 0.052(3) 0.049(3) -0.023(2) 0.002(2) -0.019(2)
C9 0.034(3) 0.072(4) 0.052(3) -0.026(3) -0.003(2) -0.010(2)
C10 0.044(3) 0.060(3) 0.056(3) -0.019(3) -0.011(2) 0.001(3)
C11 0.045(3) 0.049(3) 0.050(3) -0.013(2) -0.005(2) -0.007(2)
C12 0.032(2) 0.041(2) 0.041(2) -0.017(2) -0.0020(19) -0.0092(19)
C13 0.039(3) 0.073(4) 0.058(3) -0.031(3) 0.005(2) -0.014(3)
C14 0.042(3) 0.127(6) 0.037(3) -0.022(3) 0.010(2) -0.026(3)
C15 0.057(4) 0.204(10) 0.070(4) -0.085(6) 0.025(3) -0.063(5)
C16 0.126(7) 0.186(10) 0.117(7) -0.110(7) 0.062(6) -0.100(7)
C17 0.209(13) 0.265(16) 0.196(13) -0.186(13) 0.136(11) -0.157(13)
C18 0.161(12) 0.53(3) 0.166(12) -0.271(19) 0.087(10) -0.205(17)
C19 0.097(8) 0.48(4) 0.144(11) -0.173(19) 0.043(8) -0.083(14)
C20 0.065(6) 0.42(2) 0.091(7) -0.154(12) 0.016(5) -0.060(9)
C21 0.085(8) 0.51(4) 0.082(8) -0.132(16) -0.017(6) -0.002(13)
C22 0.098(7) 0.252(16) 0.058(5) 0.032(7) 0.002(5) 0.052(9)
C23 0.175(14) 0.33(3) 0.106(10) -0.025(15) 0.007(9) 0.035(16)
C24 0.28(2) 0.155(14) 0.129(11) 0.092(11) 0.013(11) 0.051(12)
C25 0.209(14) 0.103(8) 0.182(13) 0.046(9) 0.051(11) -0.006(8)
C26 0.139(8) 0.084(6) 0.104(7) 0.026(5) 0.034(6) -0.019(6)
C27 0.074(5) 0.120(7) 0.051(4) 0.002(4) 0.008(3) 0.004(5)
C29 0.043(3) 0.044(3) 0.060(3) -0.023(2) -0.006(2) -0.005(2)
N1 0.115(6) 0.068(4) 0.148(7) -0.060(5) 0.067(5) -0.031(4)
N2 0.043(2) 0.037(2) 0.060(3) -0.0186(19) -0.0089(19) -0.0099(18)
N3 0.035(2) 0.041(2) 0.046(2) -0.0167(18) -0.0019(16) -0.0110(16)
O1 0.215(8) 0.044(3) 0.148(6) -0.019(4) 0.046(5) -0.022(4)
O2 0.130(5) 0.091(4) 0.241(8) -0.110(5) 0.042(5) -0.053(4)
O3 0.049(2) 0.070(2) 0.083(3) -0.036(2) -0.0130(19) -0.0181(18)
_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
C1 C2 1.335(10) . ?
C1 C6 1.383(10) . ?
C1 N1 1.473(9) . ?
C2 C3 1.363(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(7) . ?
C3 H3 0.9300 . ?
C4 N2 1.378(6) . ?
C4 C5 1.390(8) . ?
C5 C6 1.390(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.384(6) . ?
C7 N2 1.404(6) . ?
C7 C12 1.407(6) . ?
C8 C9 1.374(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.368(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(7) . ?
C11 H11 0.9300 . ?
C12 N3 1.425(5) . ?
C13 N3 1.456(6) . ?
C13 C14 1.547(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.401(8) . ?
C14 C27 1.402(7) . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 C17 1.3900 . ?
C16 H16 0.9300 . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C18 C19 1.3900 . ?
C18 H18 0.9300 . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 C21 1.392(12) . ?
C21 C22 1.393(13) . ?
C21 H21 0.9300 . ?
C22 C23 1.3900 . ?
C22 C27 1.3900 . ?
C23 C24 1.3900 . ?
C23 H23 0.9300 . ?
C24 C25 1.3900 . ?
C24 H24 0.9300 . ?
C25 C26 1.3900 . ?
C25 H25 0.9300 . ?
C26 C27 1.3900 . ?
C26 H26 0.9300 . ?
C29 O3 1.230(6) . ?
C29 N3 1.326(6) . ?
C29 H29 0.9300 . ?
N1 O1 1.197(10) . ?
N1 O2 1.263(10) . ?
N2 H2A 0.8600 . ?
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
C2 C1 C6 121.2(5) . . ?
C2 C1 N1 121.4(7) . . ?
C6 C1 N1 117.4(8) . . ?
C1 C2 C3 120.6(6) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 120.7(6) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
N2 C4 C5 120.1(5) . . ?
N2 C4 C3 121.4(5) . . ?
C5 C4 C3 118.4(5) . . ?
C4 C5 C6 119.7(6) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 119.4(6) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 N2 121.8(4) . . ?
C8 C7 C12 117.7(4) . . ?
N2 C7 C12 120.2(4) . . ?
C9 C8 C7 120.7(4) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 121.0(5) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 119.3(5) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 120.6(5) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 120.7(4) . . ?
C11 C12 N3 119.8(4) . . ?
C7 C12 N3 119.5(4) . . ?
N3 C13 C14 110.8(4) . . ?
N3 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C15 C14 C27 125.2(5) . . ?
C15 C14 C13 119.1(4) . . ?
C27 C14 C13 115.7(4) . . ?
C16 C15 C20 120.0 . . ?
C16 C15 C14 129.5(3) . . ?
C20 C15 C14 110.5(3) . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 120.0 . . ?
C19 C20 C21 109.3(5) . . ?
C15 C20 C21 130.7(5) . . ?
C20 C21 C22 112.8(6) . . ?
C20 C21 H21 123.6 . . ?
C22 C21 H21 123.6 . . ?
C23 C22 C27 120.0 . . ?
C23 C22 C21 116.6(6) . . ?
C27 C22 C21 123.4(6) . . ?
C22 C23 C24 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C27 C26 C25 120.0 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C22 120.0 . . ?
C26 C27 C14 122.7(4) . . ?
C22 C27 C14 117.2(5) . . ?
O3 C29 N3 125.4(5) . . ?
O3 C29 H29 117.3 . . ?
N3 C29 H29 117.3 . . ?
O1 N1 O2 123.8(7) . . ?
O1 N1 C1 121.2(9) . . ?
O2 N1 C1 115.0(9) . . ?
C4 N2 C7 125.8(4) . . ?
C4 N2 H2A 117.1 . . ?
C7 N2 H2A 117.1 . . ?
C29 N3 C12 119.0(4) . . ?
C29 N3 C13 119.2(4) . . ?
C12 N3 C13 121.3(4) . . ?
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 -0.6(10) . . . . ?
N1 C1 C2 C3 180.0(6) . . . . ?
C1 C2 C3 C4 -1.3(9) . . . . ?
C2 C3 C4 N2 -179.9(5) . . . . ?
C2 C3 C4 C5 2.3(9) . . . . ?
N2 C4 C5 C6 -179.2(5) . . . . ?
C3 C4 C5 C6 -1.5(9) . . . . ?
C2 C1 C6 C5 1.4(10) . . . . ?
N1 C1 C6 C5 -179.1(6) . . . . ?
C4 C5 C6 C1 -0.4(9) . . . . ?
N2 C7 C8 C9 175.9(4) . . . . ?
C12 C7 C8 C9 2.2(7) . . . . ?
C7 C8 C9 C10 -4.2(8) . . . . ?
C8 C9 C10 C11 4.4(8) . . . . ?
C9 C10 C11 C12 -2.7(8) . . . . ?
C10 C11 C12 C7 0.8(7) . . . . ?
C10 C11 C12 N3 -178.7(4) . . . . ?
C8 C7 C12 C11 -0.5(7) . . . . ?
N2 C7 C12 C11 -174.4(4) . . . . ?
C8 C7 C12 N3 178.9(4) . . . . ?
N2 C7 C12 N3 5.1(6) . . . . ?
N3 C13 C14 C15 -107.5(5) . . . . ?
N3 C13 C14 C27 71.7(5) . . . . ?
C27 C14 C15 C16 178.8(4) . . . . ?
C13 C14 C15 C16 -2.2(7) . . . . ?
C27 C14 C15 C20 -2.1(6) . . . . ?
C13 C14 C15 C20 177.0(4) . . . . ?
C20 C15 C16 C17 0.0 . . . . ?
C14 C15 C16 C17 179.0(5) . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C15 0.0 . . . . ?
C18 C19 C20 C21 -178.6(8) . . . . ?
C16 C15 C20 C19 0.0 . . . . ?
C14 C15 C20 C19 -179.2(4) . . . . ?
C16 C15 C20 C21 178.3(10) . . . . ?
C14 C15 C20 C21 -0.9(9) . . . . ?
C19 C20 C21 C22 179.6(7) . . . . ?
C15 C20 C21 C22 1.2(15) . . . . ?
C20 C21 C22 C23 179.8(7) . . . . ?
C20 C21 C22 C27 1.5(14) . . . . ?
C27 C22 C23 C24 0.0 . . . . ?
C21 C22 C23 C24 -178.4(9) . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 C22 0.0 . . . . ?
C25 C26 C27 C14 -177.6(6) . . . . ?
C23 C22 C27 C26 0.0 . . . . ?
C21 C22 C27 C26 178.2(10) . . . . ?
C23 C22 C27 C14 177.7(5) . . . . ?
C21 C22 C27 C14 -4.0(10) . . . . ?
C15 C14 C27 C26 -177.9(5) . . . . ?
C13 C14 C27 C26 3.0(7) . . . . ?
C15 C14 C27 C22 4.5(7) . . . . ?
C13 C14 C27 C22 -174.6(4) . . . . ?
C2 C1 N1 O1 178.3(7) . . . . ?
C6 C1 N1 O1 -1.1(10) . . . . ?
C2 C1 N1 O2 -0.6(10) . . . . ?
C6 C1 N1 O2 180.0(6) . . . . ?
C5 C4 N2 C7 -146.6(5) . . . . ?
C3 C4 N2 C7 35.7(8) . . . . ?
C8 C7 N2 C4 25.1(7) . . . . ?
C12 C7 N2 C4 -161.3(5) . . . . ?
O3 C29 N3 C12 -174.6(4) . . . . ?
O3 C29 N3 C13 -2.8(7) . . . . ?
C11 C12 N3 C29 69.0(6) . . . . ?
C7 C12 N3 C29 -110.5(5) . . . . ?
C11 C12 N3 C13 -102.6(5) . . . . ?
C7 C12 N3 C13 77.9(6) . . . . ?
C14 C13 N3 C29 -134.1(4) . . . . ?
C14 C13 N3 C12 37.5(5) . . . . ?
_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.132


data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 916000'
#TrackingRef 'py_cn_0m.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H21 N3 O3, C2 H6 O S'
_chemical_formula_sum            'C32 H27 N3 O4 S'
_chemical_formula_weight         549.63
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                   12.604(8)
_cell_length_b                   9.138(4)
_cell_length_c                   23.915(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.91(2)
_cell_angle_gamma                90.00
_cell_volume                     2728(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3627
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      23.39
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.600
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17751
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0693
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         27.26
_reflns_number_total             5828
_reflns_number_gt                3120
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-92 (Altomare et al.,1992)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0984P)^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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5828
_refine_ls_number_parameters     369
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1377
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.1955
_refine_ls_wR_factor_gt          0.1574
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_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
C1 C 0.3912(3) 0.1742(5) 0.98078(14) 0.0728(10) Uani 1 1 d . A .
C2 C 0.3157(3) 0.0773(4) 0.99450(14) 0.0744(10) Uani 1 1 d . . .
H2 H 0.2857 0.0090 0.9681 0.089 Uiso 1 1 calc R . .
C3 C 0.2843(3) 0.0814(4) 1.04765(13) 0.0595(8) Uani 1 1 d . . .
H3 H 0.2348 0.0139 1.0574 0.071 Uiso 1 1 calc R . .
C4 C 0.3268(2) 0.1867(3) 1.08658(11) 0.0434(7) Uani 1 1 d . . .
C5 C 0.4004(2) 0.2863(4) 1.07077(12) 0.0531(7) Uani 1 1 d . . .
H5 H 0.4287 0.3578 1.0962 0.064 Uiso 1 1 calc R . .
C6 C 0.4321(3) 0.2810(4) 1.01809(14) 0.0682(10) Uani 1 1 d . . .
H6 H 0.4808 0.3490 1.0078 0.082 Uiso 1 1 calc R . .
C7 C 0.2348(2) 0.1000(3) 1.16522(10) 0.0392(6) Uani 1 1 d . . .
C8 C 0.2557(2) -0.0492(3) 1.16514(12) 0.0500(7) Uani 1 1 d . . .
H8 H 0.3115 -0.0837 1.1470 0.060 Uiso 1 1 calc R . .
C9 C 0.1957(3) -0.1467(3) 1.19120(12) 0.0562(8) Uani 1 1 d . . .
H9 H 0.2103 -0.2463 1.1902 0.067 Uiso 1 1 calc R . .
C10 C 0.1146(3) -0.0974(4) 1.21865(12) 0.0604(8) Uani 1 1 d . . .
H10 H 0.0739 -0.1634 1.2362 0.073 Uiso 1 1 calc R . .
C11 C 0.0932(2) 0.0499(3) 1.22031(11) 0.0523(7) Uani 1 1 d . . .
H11 H 0.0379 0.0828 1.2391 0.063 Uiso 1 1 calc R . .
C12 C 0.1532(2) 0.1500(3) 1.19425(11) 0.0409(6) Uani 1 1 d . . .
C13 C 0.0331(2) 0.3544(4) 1.15723(12) 0.0572(8) Uani 1 1 d . . .
H13A H 0.0260 0.4592 1.1618 0.069 Uiso 1 1 calc R . .
H13B H -0.0305 0.3084 1.1679 0.069 Uiso 1 1 calc R . .
C14 C 0.0391(2) 0.3219(3) 1.09625(12) 0.0514(7) Uani 1 1 d . . .
C15 C -0.0259(3) 0.2116(4) 1.07033(14) 0.0637(9) Uani 1 1 d . . .
H15 H -0.0700 0.1594 1.0913 0.076 Uiso 1 1 calc R . .
C16 C -0.0263(3) 0.1784(4) 1.01416(15) 0.0678(9) Uani 1 1 d . . .
H16 H -0.0706 0.1039 0.9980 0.081 Uiso 1 1 calc R . .
C17 C 0.0370(3) 0.2524(4) 0.98162(13) 0.0615(9) Uani 1 1 d . . .
C18 C 0.0395(3) 0.2212(5) 0.92315(16) 0.0801(12) Uani 1 1 d . . .
H18 H -0.0034 0.1464 0.9061 0.096 Uiso 1 1 calc R . .
C19 C 0.1010(3) 0.2954(5) 0.89262(15) 0.0837(13) Uani 1 1 d . . .
H19 H 0.1008 0.2696 0.8550 0.100 Uiso 1 1 calc R . .
C20 C 0.1677(3) 0.4136(5) 0.91523(14) 0.0740(11) Uani 1 1 d . . .
C21 C 0.2301(4) 0.4984(7) 0.88474(17) 0.0978(16) Uani 1 1 d . . .
H21 H 0.2305 0.4774 0.8467 0.117 Uiso 1 1 calc R . .
C22 C 0.2913(4) 0.6122(6) 0.9083(2) 0.0999(15) Uani 1 1 d . . .
H22 H 0.3318 0.6669 0.8861 0.120 Uiso 1 1 calc R . .
C23 C 0.2933(3) 0.6467(5) 0.96519(17) 0.0831(12) Uani 1 1 d . . .
H23 H 0.3350 0.7242 0.9809 0.100 Uiso 1 1 calc R . .
C24 C 0.2329(3) 0.5651(4) 0.99845(14) 0.0634(9) Uani 1 1 d . . .
C25 C 0.2330(3) 0.5956(4) 1.05767(14) 0.0605(8) Uani 1 1 d . . .
H25 H 0.2760 0.6703 1.0747 0.073 Uiso 1 1 calc R . .
C26 C 0.1723(2) 0.5184(3) 1.08835(12) 0.0524(8) Uani 1 1 d . . .
H26 H 0.1741 0.5410 1.1264 0.063 Uiso 1 1 calc R . .
C27 C 0.1046(2) 0.4018(3) 1.06474(11) 0.0464(7) Uani 1 1 d . . .
C28 C 0.1047(2) 0.3678(3) 1.00664(11) 0.0508(8) Uani 1 1 d . . .
C29 C 0.1688(3) 0.4490(4) 0.97402(12) 0.0570(8) Uani 1 1 d . . .
C30 C 0.1762(2) 0.3905(3) 1.23621(12) 0.0472(7) Uani 1 1 d . . .
H30 H 0.2308 0.3499 1.2616 0.057 Uiso 1 1 calc R . .
C31 C 0.4207(3) 0.6305(4) 1.28451(14) 0.0800(11) Uani 1 1 d D . .
H31A H 0.3493 0.6188 1.2936 0.120 Uiso 1 1 calc R . .
H31B H 0.4436 0.7297 1.2916 0.120 Uiso 1 1 calc R . .
H31C H 0.4683 0.5656 1.3075 0.120 Uiso 1 1 calc R . .
C32 C 0.5591(3) 0.6185(4) 1.20998(15) 0.0744(10) Uani 1 1 d D . .
H32A H 0.5750 0.6001 1.1725 0.112 Uiso 1 1 calc R . .
H32B H 0.6006 0.5538 1.2360 0.112 Uiso 1 1 calc R . .
H32C H 0.5766 0.7181 1.2202 0.112 Uiso 1 1 calc R . .
N1 N 0.4263(4) 0.1648(6) 0.92537(16) 0.1144(14) Uani 1 1 d . . .
N2 N 0.29637(18) 0.2002(3) 1.13922(9) 0.0444(6) Uani 1 1 d D . .
H2A H 0.318(2) 0.280(2) 1.1563(11) 0.053 Uiso 1 1 d D . .
N3 N 0.12751(17) 0.3030(2) 1.19551(9) 0.0424(6) Uani 1 1 d . . .
O1 O 0.5006(3) 0.2451(5) 0.91633(13) 0.1441(16) Uani 1 1 d . A .
O2 O 0.3626(14) 0.1004(18) 0.8867(5) 0.132(3) Uani 0.608(19) 1 d P A 1
O2' O 0.411(2) 0.057(3) 0.8976(8) 0.132(3) Uani 0.392(19) 1 d P A 2
O3 O 0.15461(18) 0.5192(3) 1.24261(9) 0.0661(6) Uani 1 1 d . . .
O4 O 0.40568(18) 0.4275(2) 1.20655(10) 0.0693(7) Uani 1 1 d D . .
S1 S 0.42245(6) 0.58835(9) 1.21225(3) 0.0539(3) Uani 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
C1 0.075(2) 0.096(3) 0.0505(19) 0.0022(19) 0.0218(17) 0.013(2)
C2 0.091(3) 0.077(3) 0.053(2) -0.0182(17) 0.0041(18) 0.005(2)
C3 0.064(2) 0.060(2) 0.0540(18) -0.0083(15) 0.0062(15) -0.0091(16)
C4 0.0373(15) 0.0473(18) 0.0456(15) -0.0006(12) 0.0054(11) 0.0064(12)
C5 0.0473(17) 0.057(2) 0.0564(18) 0.0009(14) 0.0114(13) -0.0005(14)
C6 0.060(2) 0.084(3) 0.063(2) 0.0117(19) 0.0181(16) 0.0046(19)
C7 0.0380(14) 0.0399(17) 0.0379(14) -0.0020(11) -0.0012(11) -0.0002(11)
C8 0.0517(17) 0.0422(19) 0.0553(17) -0.0073(13) 0.0044(13) 0.0038(13)
C9 0.078(2) 0.0350(18) 0.0530(17) -0.0006(13) -0.0002(15) -0.0016(15)
C10 0.082(2) 0.047(2) 0.0538(18) 0.0064(14) 0.0124(16) -0.0159(17)
C11 0.0568(19) 0.054(2) 0.0476(17) 0.0012(14) 0.0140(13) -0.0047(15)
C12 0.0416(15) 0.0388(17) 0.0412(14) -0.0006(11) 0.0022(11) 0.0023(12)
C13 0.0521(18) 0.063(2) 0.0566(18) 0.0053(15) 0.0087(14) 0.0209(15)
C14 0.0465(17) 0.049(2) 0.0564(18) 0.0035(14) -0.0020(13) 0.0149(14)
C15 0.053(2) 0.060(2) 0.074(2) 0.0045(17) -0.0031(16) 0.0044(16)
C16 0.055(2) 0.063(2) 0.079(2) -0.0080(18) -0.0144(17) 0.0018(16)
C17 0.060(2) 0.067(2) 0.0509(18) -0.0139(16) -0.0153(15) 0.0207(17)
C18 0.081(3) 0.091(3) 0.061(2) -0.020(2) -0.015(2) 0.019(2)
C19 0.085(3) 0.117(4) 0.0419(19) -0.023(2) -0.0157(19) 0.041(3)
C20 0.062(2) 0.109(3) 0.0494(19) 0.004(2) 0.0027(16) 0.040(2)
C21 0.069(3) 0.168(5) 0.058(2) 0.016(3) 0.015(2) 0.046(3)
C22 0.068(3) 0.145(5) 0.092(3) 0.041(3) 0.031(2) 0.021(3)
C23 0.063(2) 0.105(3) 0.083(3) 0.027(2) 0.0186(19) 0.013(2)
C24 0.054(2) 0.072(3) 0.064(2) 0.0110(17) 0.0074(16) 0.0228(17)
C25 0.063(2) 0.053(2) 0.064(2) -0.0017(15) 0.0022(15) 0.0068(15)
C26 0.068(2) 0.0443(18) 0.0421(16) -0.0056(13) -0.0022(14) 0.0097(15)
C27 0.0465(16) 0.0458(18) 0.0436(15) -0.0024(12) -0.0056(12) 0.0178(13)
C28 0.0501(17) 0.054(2) 0.0441(16) -0.0041(14) -0.0063(13) 0.0219(14)
C29 0.0532(19) 0.070(2) 0.0452(17) 0.0012(15) -0.0014(14) 0.0269(17)
C30 0.0488(17) 0.044(2) 0.0506(17) 0.0012(13) 0.0134(13) 0.0006(13)
C31 0.100(3) 0.084(3) 0.061(2) -0.0223(18) 0.0253(19) -0.029(2)
C32 0.067(2) 0.080(3) 0.079(2) -0.0085(19) 0.0163(18) -0.0143(19)
N1 0.135(4) 0.152(4) 0.064(2) -0.002(2) 0.039(2) 0.013(3)
N2 0.0446(14) 0.0408(15) 0.0494(14) -0.0096(10) 0.0121(10) -0.0065(11)
N3 0.0429(13) 0.0416(14) 0.0431(13) 0.0027(10) 0.0071(10) 0.0088(10)
O1 0.132(3) 0.229(5) 0.081(2) 0.022(2) 0.052(2) -0.006(3)
O2 0.189(12) 0.149(9) 0.061(5) -0.026(5) 0.030(6) 0.029(6)
O2' 0.189(12) 0.149(9) 0.061(5) -0.026(5) 0.030(6) 0.029(6)
O3 0.0731(16) 0.0447(16) 0.0822(16) -0.0088(11) 0.0161(12) 0.0035(11)
O4 0.0777(16) 0.0482(16) 0.0811(16) -0.0192(11) 0.0078(12) -0.0150(11)
S1 0.0572(5) 0.0504(6) 0.0533(5) -0.0024(3) 0.0050(3) 0.0011(4)
_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
C1 C2 1.372(5) . ?
C1 C6 1.374(5) . ?
C1 N1 1.456(5) . ?
C2 C3 1.383(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(4) . ?
C3 H3 0.9300 . ?
C4 N2 1.371(3) . ?
C4 C5 1.389(4) . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.389(4) . ?
C7 C12 1.394(4) . ?
C7 N2 1.400(3) . ?
C8 C9 1.372(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(4) . ?
C11 H11 0.9300 . ?
C12 N3 1.436(3) . ?
C13 N3 1.474(4) . ?
C13 C14 1.500(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.390(5) . ?
C14 C27 1.397(4) . ?
C15 C16 1.376(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.432(5) . ?
C17 C28 1.434(5) . ?
C18 C19 1.322(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.428(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.382(6) . ?
C20 C29 1.441(4) . ?
C21 C22 1.369(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.394(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.391(5) . ?
C23 H23 0.9300 . ?
C24 C29 1.410(5) . ?
C24 C25 1.443(5) . ?
C25 C26 1.332(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.432(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.424(4) . ?
C28 C29 1.409(5) . ?
C30 O3 1.222(4) . ?
C30 N3 1.341(4) . ?
C30 H30 0.9300 . ?
C31 S1 1.773(3) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 S1 1.753(4) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
N1 O2' 1.19(2) . ?
N1 O1 1.232(5) . ?
N1 O2 1.281(16) . ?
N2 H2A 0.860(18) . ?
O4 S1 1.488(2) . ?
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
C2 C1 C6 120.9(3) . . ?
C2 C1 N1 119.2(4) . . ?
C6 C1 N1 119.9(4) . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
N2 C4 C5 118.2(3) . . ?
N2 C4 C3 123.0(3) . . ?
C5 C4 C3 118.7(3) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C8 C7 C12 118.4(3) . . ?
C8 C7 N2 121.6(2) . . ?
C12 C7 N2 119.9(3) . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C7 119.5(3) . . ?
C11 C12 N3 119.6(2) . . ?
C7 C12 N3 120.9(2) . . ?
N3 C13 C14 113.3(2) . . ?
N3 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
N3 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C27 119.6(3) . . ?
C15 C14 C13 118.1(3) . . ?
C27 C14 C13 122.2(3) . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 121.5(3) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 123.4(4) . . ?
C16 C17 C28 119.1(3) . . ?
C18 C17 C28 117.5(4) . . ?
C19 C18 C17 122.1(4) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C18 C19 C20 122.5(3) . . ?
C18 C19 H19 118.7 . . ?
C20 C19 H19 118.7 . . ?
C21 C20 C19 124.9(4) . . ?
C21 C20 C29 117.3(4) . . ?
C19 C20 C29 117.7(4) . . ?
C22 C21 C20 122.6(4) . . ?
C22 C21 H21 118.7 . . ?
C20 C21 H21 118.7 . . ?
C21 C22 C23 120.4(4) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 120.0(4) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C29 119.6(3) . . ?
C23 C24 C25 122.0(4) . . ?
C29 C24 C25 118.4(3) . . ?
C26 C25 C24 121.0(3) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 122.2(3) . . ?
C25 C26 H26 118.9 . . ?
C27 C26 H26 118.9 . . ?
C14 C27 C28 119.5(3) . . ?
C14 C27 C26 122.7(3) . . ?
C28 C27 C26 117.8(3) . . ?
C29 C28 C27 120.2(3) . . ?
C29 C28 C17 120.6(3) . . ?
C27 C28 C17 119.1(3) . . ?
C28 C29 C24 120.4(3) . . ?
C28 C29 C20 119.5(3) . . ?
C24 C29 C20 120.1(3) . . ?
O3 C30 N3 125.2(3) . . ?
O3 C30 H30 117.4 . . ?
N3 C30 H30 117.4 . . ?
S1 C31 H31A 109.5 . . ?
S1 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
S1 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
S1 C32 H32A 109.5 . . ?
S1 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
S1 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O2' N1 O1 117.7(13) . . ?
O1 N1 O2 124.2(7) . . ?
O2' N1 C1 120.7(13) . . ?
O1 N1 C1 117.3(5) . . ?
O2 N1 C1 116.5(8) . . ?
C4 N2 C7 126.2(2) . . ?
C4 N2 H2A 114(2) . . ?
C7 N2 H2A 120(2) . . ?
C30 N3 C12 120.9(2) . . ?
C30 N3 C13 120.7(2) . . ?
C12 N3 C13 117.5(2) . . ?
O4 S1 C32 106.26(17) . . ?
O4 S1 C31 106.43(16) . . ?
C32 S1 C31 98.05(18) . . ?
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 -3.6(6) . . . . ?
N1 C1 C2 C3 177.7(4) . . . . ?
C1 C2 C3 C4 2.0(5) . . . . ?
C2 C3 C4 N2 177.6(3) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
N2 C4 C5 C6 -178.3(3) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
C2 C1 C6 C5 3.0(6) . . . . ?
N1 C1 C6 C5 -178.3(3) . . . . ?
C12 C7 C8 C9 2.2(4) . . . . ?
N2 C7 C8 C9 179.3(2) . . . . ?
C7 C8 C9 C10 -1.0(4) . . . . ?
C8 C9 C10 C11 -0.2(5) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C10 C11 C12 C7 1.2(4) . . . . ?
C10 C11 C12 N3 178.6(3) . . . . ?
C8 C7 C12 C11 -2.2(4) . . . . ?
N2 C7 C12 C11 -179.4(2) . . . . ?
C8 C7 C12 N3 -179.6(2) . . . . ?
N2 C7 C12 N3 3.2(4) . . . . ?
N3 C13 C14 C15 106.9(3) . . . . ?
N3 C13 C14 C27 -75.4(4) . . . . ?
C27 C14 C15 C16 0.7(5) . . . . ?
C13 C14 C15 C16 178.5(3) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C15 C16 C17 C18 179.7(3) . . . . ?
C15 C16 C17 C28 -0.4(5) . . . . ?
C16 C17 C18 C19 179.5(4) . . . . ?
C28 C17 C18 C19 -0.4(5) . . . . ?
C17 C18 C19 C20 -1.2(6) . . . . ?
C18 C19 C20 C21 -177.3(4) . . . . ?
C18 C19 C20 C29 1.6(5) . . . . ?
C19 C20 C21 C22 178.9(4) . . . . ?
C29 C20 C21 C22 -0.1(6) . . . . ?
C20 C21 C22 C23 0.4(7) . . . . ?
C21 C22 C23 C24 0.1(6) . . . . ?
C22 C23 C24 C29 -0.8(5) . . . . ?
C22 C23 C24 C25 179.5(3) . . . . ?
C23 C24 C25 C26 178.2(3) . . . . ?
C29 C24 C25 C26 -1.5(5) . . . . ?
C24 C25 C26 C27 0.2(5) . . . . ?
C15 C14 C27 C28 -0.7(4) . . . . ?
C13 C14 C27 C28 -178.5(2) . . . . ?
C15 C14 C27 C26 179.0(3) . . . . ?
C13 C14 C27 C26 1.2(4) . . . . ?
C25 C26 C27 C14 -178.7(3) . . . . ?
C25 C26 C27 C28 1.0(4) . . . . ?
C14 C27 C28 C29 178.9(3) . . . . ?
C26 C27 C28 C29 -0.8(4) . . . . ?
C14 C27 C28 C17 0.3(4) . . . . ?
C26 C27 C28 C17 -179.5(3) . . . . ?
C16 C17 C28 C29 -178.3(3) . . . . ?
C18 C17 C28 C29 1.6(4) . . . . ?
C16 C17 C28 C27 0.3(4) . . . . ?
C18 C17 C28 C27 -179.8(3) . . . . ?
C27 C28 C29 C24 -0.4(4) . . . . ?
C17 C28 C29 C24 178.2(3) . . . . ?
C27 C28 C29 C20 -179.8(3) . . . . ?
C17 C28 C29 C20 -1.2(4) . . . . ?
C23 C24 C29 C28 -178.1(3) . . . . ?
C25 C24 C29 C28 1.6(4) . . . . ?
C23 C24 C29 C20 1.2(5) . . . . ?
C25 C24 C29 C20 -179.1(3) . . . . ?
C21 C20 C29 C28 178.6(3) . . . . ?
C19 C20 C29 C28 -0.4(4) . . . . ?
C21 C20 C29 C24 -0.7(5) . . . . ?
C19 C20 C29 C24 -179.7(3) . . . . ?
C2 C1 N1 O2' -17.8(14) . . . . ?
C6 C1 N1 O2' 163.5(13) . . . . ?
C2 C1 N1 O1 -173.9(4) . . . . ?
C6 C1 N1 O1 7.3(7) . . . . ?
C2 C1 N1 O2 21.6(10) . . . . ?
C6 C1 N1 O2 -157.1(9) . . . . ?
C5 C4 N2 C7 -171.0(3) . . . . ?
C3 C4 N2 C7 11.6(4) . . . . ?
C8 C7 N2 C4 46.0(4) . . . . ?
C12 C7 N2 C4 -136.9(3) . . . . ?
O3 C30 N3 C12 -175.1(3) . . . . ?
O3 C30 N3 C13 -6.3(4) . . . . ?
C11 C12 N3 C30 92.8(3) . . . . ?
C7 C12 N3 C30 -89.8(3) . . . . ?
C11 C12 N3 C13 -76.3(3) . . . . ?
C7 C12 N3 C13 101.0(3) . . . . ?
C14 C13 N3 C30 133.3(3) . . . . ?
C14 C13 N3 C12 -57.5(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.955
_diffrn_reflns_theta_full        27.26
_diffrn_measured_fraction_theta_full 0.955
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.060