# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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data_m200

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 N3 O4 S V'
_chemical_formula_sum            'C17 H12 N3 O4 S V'
_chemical_formula_weight         405.30

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'
V V 0.3005 0.5294 '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
_symmetry_space_group_name_Hall  -P2ybc


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                   10.2017(8)
_cell_length_b                   10.1819(10)
_cell_length_c                   16.4706(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.582(5)
_cell_angle_gamma                90.00
_cell_volume                     1655.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    33750
_cell_measurement_theta_min      4.735
_cell_measurement_theta_max      38.612

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8761
_exptl_absorpt_correction_T_max  0.9284
_exptl_absorpt_process_details   'North et al., 1968'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30202
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         26.45
_reflns_number_total             3389
_reflns_number_gt                2369
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS Version 2008/1 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122) '
_computing_structure_refinement  
'XL Version 2008/4 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_iucr_refine-instructions_details 
;
TITL  m200 in P 1 21/c 1
CELL   0.71073  10.2017  10.1819  16.4706  90.000 104.582  90.000
ZERR     4       0.0008   0.0010   0.0015   0.000   0.005   0.000
LATT    1
SYMM   -X,1/2+Y,1/2-Z
SFAC  C    H    N    O    S    V
UNIT  68   48   12   16   4    4
TEMP    20
SIZE  0.100   0.160   0.180
 
MERG    2
L.S.    30
FMAP    2
PLAN    -10
SADI C8 C9A C9A C10A C10A C11A C11A C12A C12A C13A C13A C8
SADI C8 C9B C9B C10B C10B C11B C11B C12B C12B C13B C13B C8
SIMU C8 C9A C10A C11A C12A C13A C9B C10B C11B C12B C13B
FLAT 0.001 C8 C9A C10A C11A C12A C13A
FLAT 0.001 C8 C9B C10B C11B C12B C13B
SADI C4 C5A C4 C5B
SADI C4 S1A C4 S1B
SIMU C4 C5A C5B S1A S1B C6 C7
DELU C4 C5A C5B S1A S1B C6 C7
ACTA
CONF
WPDB -1
HTAB
BOND $H
WGHT    0.079200    2.265900
EXTI    0.002159
FVAR       0.08820   0.48745   0.51932
V1    6    0.344667    0.017342    0.432968    11.00000    0.03764    0.03219 =
         0.03606   -0.00317    0.01556   -0.00913
O1    4    0.378837    0.176619    0.371872    11.00000    0.03851    0.02469 =
         0.04448   -0.00242    0.01987   -0.00207
N1    3    0.272021   -0.061719    0.532484    11.00000    0.04259    0.06001 =
         0.03688   -0.00517    0.01134   -0.02287
C1    1    0.195882    0.018315    0.568417    11.00000    0.04895    0.08328 =
         0.04329   -0.02105    0.02211   -0.03589
PART   1
S1A   5    0.447469    0.398442    0.276610    31.00000    0.04270    0.02366 =
         0.04347   -0.00252    0.01121   -0.00097
PART   2
S1B   5    0.364089    0.557601    0.406039   -31.00000    0.12509    0.02625 =
         0.03866   -0.00193    0.01518    0.01228
PART   0
O2    4    0.473117   -0.117734    0.462530    11.00000    0.04928    0.03765 =
         0.03682    0.00290    0.01639   -0.00439
N2    3    0.255564    0.173122    0.482028    11.00000    0.03665    0.04726 =
         0.04844   -0.01144    0.01844   -0.01266
C2    1    0.194850    0.155174    0.542081    11.00000    0.03228    0.07516 =
         0.05307   -0.02533    0.02004   -0.02089
O3    4    0.213642   -0.039711    0.369148    11.00000    0.04135    0.04259 =
         0.03911    0.00117    0.01100   -0.01308
N3    3    0.269152    0.298295    0.454044    11.00000    0.03440    0.04201 =
         0.05506   -0.01015    0.01461   -0.00034
C3    1    0.339356    0.287805    0.396666    11.00000    0.02991    0.03196 =
         0.04331   -0.00473    0.00541    0.00204
O4    4    0.482337   -0.048496    0.388781    11.00000    0.04486    0.03315 =
         0.03732    0.00150    0.01663   -0.00440
C4    1    0.378269    0.407230    0.361037    11.00000    0.04041    0.02707 =
         0.04056   -0.00285    0.00148    0.00285
PART   1
C5A   1    0.367127    0.532779    0.383330    31.00000    0.09832    0.04412 =
         0.03209   -0.00544    0.01796    0.01928
AFIX  43
H5A   2    0.328052    0.556540    0.426468    31.00000   -1.20000
AFIX   0
PART   2
C5B   1    0.438610    0.421453    0.296346   -31.00000    0.07553    0.02656 =
         0.03961   -0.01315    0.00296   -0.00793
AFIX  43
H5B   2    0.462667    0.350810    0.267339   -31.00000   -1.20000
AFIX   0
PART   0
C6    1    0.461771    0.558402    0.277054    11.00000    0.11449    0.02884 =
         0.03620   -0.00153    0.01558   -0.00675
AFIX  43
H6    2    0.498062    0.600091    0.237428    11.00000   -1.20000
AFIX   0
C7    1    0.421041    0.629001    0.334663    11.00000    0.18939    0.02586 =
         0.03993   -0.00012    0.02925    0.00099
AFIX  43
H7    2    0.426006    0.719580    0.342068    11.00000   -1.20000
AFIX   0
C8    1    0.141158    0.256562    0.586464    11.00000    0.03558    0.09847 =
         0.07159   -0.04627    0.02862   -0.02651
PART   1
C9A   1    0.148139    0.287293    0.661310    21.00000    0.03080    0.04283 =
         0.02969    0.00057    0.00462    0.00063
AFIX  43
H9A   2    0.198396    0.230139    0.701276    21.00000   -1.20000
AFIX   0
PART   2
C9B   1    0.225253    0.347162    0.630415   -21.00000    0.04004    0.04682 =
         0.04474   -0.00744    0.01111   -0.00448
AFIX  43
H9B   2    0.313681    0.354143    0.625235   -21.00000   -1.20000
AFIX   0
PART   1
C10A  1    0.092921    0.392334    0.693099    21.00000    0.05687    0.07144 =
         0.05197   -0.02393    0.03683   -0.02182
AFIX  43
H10A  2    0.109095    0.399173    0.751086    21.00000   -1.20000
AFIX   0
PART   2
C10B  1    0.179674    0.428440    0.682494   -21.00000    0.06238    0.04020 =
         0.02858   -0.00370    0.01139   -0.00616
AFIX  43
H10B  2    0.237299    0.491552    0.713224   -21.00000   -1.20000
AFIX   0
PART   1
C11A  1    0.016726    0.486372    0.645865    21.00000    0.03203    0.03726 =
         0.07161   -0.01006    0.02769   -0.00915
AFIX  43
H11A  2   -0.018095    0.555370    0.670982    21.00000   -1.20000
AFIX   0
PART   2
C11B  1    0.050145    0.418464    0.690206   -21.00000    0.08029    0.04512 =
         0.05675   -0.01977    0.05213   -0.01498
AFIX  43
H11B  2    0.019598    0.474590    0.726052   -21.00000   -1.20000
AFIX   0
PART   1
C12A  1   -0.008643    0.478382    0.559606    21.00000    0.03377    0.03032 =
         0.05696    0.00013    0.01921   -0.00150
AFIX  43
H12A  2   -0.060674    0.541192    0.524888    21.00000   -1.20000
AFIX   0
PART   2
C12B  1   -0.035680    0.324792    0.644656   -21.00000    0.04073    0.06322 =
         0.04998    0.01237    0.02271    0.00579
AFIX  43
H12B  2   -0.123978    0.318481    0.650161   -21.00000   -1.20000
AFIX   0
PART   1
C13A  1    0.048188    0.370109    0.526304    21.00000    0.02709    0.03896 =
         0.03784    0.00064    0.01369    0.00358
AFIX  43
H13A  2    0.032634    0.362566    0.468385    21.00000   -1.20000
AFIX   0
PART   2
C13B  1    0.006725    0.241852    0.592025   -21.00000    0.02992    0.05711 =
         0.05626   -0.00680    0.01759   -0.01144
AFIX  43
H13B  2   -0.050316    0.178437    0.561170   -21.00000   -1.20000
AFIX   0
PART   0
C14   1    0.127918   -0.031074    0.624311    11.00000    0.09735    0.11258 =
         0.06689   -0.04640    0.05777   -0.07669
AFIX  43
H14   2    0.074702    0.024031    0.647796    11.00000   -1.20000
AFIX   0
C15   1    0.139029   -0.160849    0.644983    11.00000    0.12015    0.12842 =
         0.05411   -0.03496    0.05411   -0.09202
AFIX  43
H15   2    0.092184   -0.194657    0.681983    11.00000   -1.20000
AFIX   0
C16   1    0.219285   -0.241951    0.611306    11.00000    0.08221    0.08368 =
         0.04265    0.00072    0.01375   -0.05585
AFIX  43
H16   2    0.229428   -0.330279    0.625917    11.00000   -1.20000
AFIX   0
C17   1    0.284798   -0.187919    0.554762    11.00000    0.05749    0.06403 =
         0.03833   -0.00130    0.01050   -0.03540
AFIX  43
H17   2    0.339557   -0.241713    0.531602    11.00000   -1.20000
 
HKLF  4
 
REM   m200 in P 1 21/c 1
REM R1 =  0.0601 for   2369 Fo > 4sig(Fo)  and  0.0899 for all   3389 data
REM    301 parameters refined using    225 restraints
 
END  
     
WGHT      0.0791      2.2775 
REM Highest difference peak  0.820,  deepest hole -0.853,  1-sigma level  0.087
Q1    1   0.2378  0.3172  0.6445  11.00000  0.05    0.82
Q2    1   0.0179  0.2158  0.6098  11.00000  0.05    0.81
Q3    1   0.1242  0.2960  0.5672  11.00000  0.05    0.69
Q4    1   0.0595  0.4031  0.5214  11.00000  0.05    0.59
Q5    1   0.1192 -0.1156  0.6412  11.00000  0.05    0.44
Q6    1   0.2172 -0.1878  0.6510  11.00000  0.05    0.43
Q7    1   0.1687  0.3093  0.6430  11.00000  0.05    0.42
Q8    1   0.3837  0.6437  0.3313  11.00000  0.05    0.33
Q9    1   0.1104  0.0061  0.6069  11.00000  0.05    0.32
Q10   1   0.2031 -0.0353  0.6396  11.00000  0.05    0.29
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0792P)²+2.2659P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0022(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3389
_refine_ls_number_parameters     301
_refine_ls_number_restraints     225
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1682
_refine_ls_wR_factor_gt          0.1500
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.240
_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
V1 V 0.34467(8) 0.01734(8) 0.43297(5) 0.0342(3) Uani 1 1 d . . .
O1 O 0.3788(3) 0.1766(3) 0.37187(19) 0.0342(7) Uani 1 1 d . . .
N1 N 0.2720(4) -0.0617(5) 0.5325(2) 0.0463(11) Uani 1 1 d . . .
C1 C 0.1959(6) 0.0183(7) 0.5684(3) 0.0566(16) Uani 1 1 d . . .
S1A S 0.4475(6) 0.3984(4) 0.2766(3) 0.0365(10) Uani 0.519(6) 1 d PDU A 1
S1B S 0.3641(10) 0.5576(5) 0.4060(4) 0.0643(16) Uani 0.481(6) 1 d PDU A 2
O2 O 0.4731(3) -0.1177(3) 0.46253(19) 0.0403(8) Uani 1 1 d . . .
N2 N 0.2556(4) 0.1731(4) 0.4820(3) 0.0427(10) Uani 1 1 d . . .
C2 C 0.1949(5) 0.1552(6) 0.5421(3) 0.0518(15) Uani 1 1 d . C .
O3 O 0.2136(3) -0.0397(3) 0.3691(2) 0.0409(8) Uani 1 1 d . . .
N3 N 0.2692(4) 0.2983(4) 0.4540(3) 0.0432(10) Uani 1 1 d . . .
C3 C 0.3394(4) 0.2878(4) 0.3967(3) 0.0357(10) Uani 1 1 d . A .
O4 O 0.4823(3) -0.0485(3) 0.38878(19) 0.0373(8) Uani 1 1 d . . .
C4 C 0.3783(5) 0.4072(4) 0.3610(3) 0.0376(10) Uani 1 1 d DU . .
C5A C 0.367(3) 0.5328(19) 0.3833(13) 0.058(4) Uani 0.519(6) 1 d PDU A 1
H5A H 0.3281 0.5565 0.4265 0.069 Uiso 0.519(6) 1 calc PR A 1
C5B C 0.439(3) 0.421(2) 0.2963(14) 0.049(5) Uani 0.481(6) 1 d PDU A 2
H5B H 0.4627 0.3508 0.2673 0.059 Uiso 0.481(6) 1 calc PR A 2
C6 C 0.4618(7) 0.5584(5) 0.2771(3) 0.0604(16) Uani 1 1 d U . .
H6 H 0.4981 0.6001 0.2374 0.073 Uiso 1 1 calc R A 1
C7 C 0.4210(9) 0.6290(6) 0.3347(3) 0.085(2) Uani 1 1 d U A .
H7 H 0.4260 0.7196 0.3421 0.102 Uiso 1 1 calc R B 1
C8 C 0.1412(4) 0.2566(5) 0.5865(3) 0.0658(19) Uani 1 1 d DU . .
C9A C 0.1481(7) 0.2873(8) 0.6613(5) 0.035(2) Uani 0.487(6) 1 d PDU C 1
H9A H 0.1984 0.2301 0.7013 0.042 Uiso 0.487(6) 1 calc PR C 1
C9B C 0.2253(9) 0.3472(7) 0.6304(4) 0.044(2) Uani 0.513(6) 1 d PDU C 2
H9B H 0.3137 0.3541 0.6252 0.053 Uiso 0.513(6) 1 calc PR C 2
C10A C 0.0929(10) 0.3923(12) 0.6931(12) 0.056(5) Uani 0.487(6) 1 d PDU C 1
H10A H 0.1091 0.3992 0.7511 0.067 Uiso 0.487(6) 1 calc PR C 1
C10B C 0.1797(12) 0.4284(9) 0.6825(5) 0.044(2) Uani 0.513(6) 1 d PDU C 2
H10B H 0.2373 0.4916 0.7132 0.052 Uiso 0.513(6) 1 calc PR C 2
C11A C 0.0167(8) 0.4864(10) 0.6459(7) 0.044(3) Uani 0.487(6) 1 d PDU C 1
H11A H -0.0181 0.5554 0.6710 0.053 Uiso 0.487(6) 1 calc PR C 1
C11B C 0.0501(14) 0.4185(13) 0.6902(9) 0.054(4) Uani 0.513(6) 1 d PDU C 2
H11B H 0.0196 0.4746 0.7261 0.065 Uiso 0.513(6) 1 calc PR C 2
C12A C -0.0086(8) 0.4784(8) 0.5596(6) 0.039(2) Uani 0.487(6) 1 d PDU C 1
H12A H -0.0607 0.5412 0.5249 0.047 Uiso 0.487(6) 1 calc PR C 1
C12B C -0.0357(10) 0.3248(9) 0.6447(5) 0.049(3) Uani 0.513(6) 1 d PDU C 2
H12B H -0.1240 0.3185 0.6502 0.059 Uiso 0.513(6) 1 calc PR C 2
C13A C 0.0482(7) 0.3701(7) 0.5263(6) 0.034(2) Uani 0.487(6) 1 d PDU C 1
H13A H 0.0326 0.3626 0.4684 0.040 Uiso 0.487(6) 1 calc PR C 1
C13B C 0.0067(8) 0.2419(9) 0.5920(5) 0.047(3) Uani 0.513(6) 1 d PDU C 2
H13B H -0.0503 0.1784 0.5612 0.056 Uiso 0.513(6) 1 calc PR C 2
C14 C 0.1279(8) -0.0311(8) 0.6243(4) 0.086(3) Uani 1 1 d . . .
H14 H 0.0747 0.0240 0.6478 0.103 Uiso 1 1 calc R . .
C15 C 0.1390(8) -0.1608(9) 0.6450(4) 0.095(3) Uani 1 1 d . . .
H15 H 0.0922 -0.1947 0.6820 0.114 Uiso 1 1 calc R . .
C16 C 0.2193(7) -0.2420(7) 0.6113(3) 0.070(2) Uani 1 1 d . . .
H16 H 0.2294 -0.3303 0.6259 0.084 Uiso 1 1 calc R . .
C17 C 0.2848(6) -0.1879(6) 0.5548(3) 0.0536(15) Uani 1 1 d . . .
H17 H 0.3396 -0.2417 0.5316 0.064 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O3 1.588(3) . ?
V1 O4 1.862(3) . ?
V1 O2 1.877(3) . ?
V1 O1 1.985(3) . ?
V1 N2 2.089(4) . ?
V1 N1 2.120(4) . ?
V1 O2 2.419(3) 3_656 ?
O1 C3 1.301(5) . ?
N1 C17 1.334(7) . ?
N1 C1 1.360(7) . ?
C1 C14 1.379(7) . ?
C1 C2 1.459(9) . ?
S1A C6 1.635(7) . ?
S1A C4 1.713(6) . ?
S1B C7 1.610(9) . ?
S1B C4 1.723(6) . ?
O2 O4 1.428(4) . ?
O2 V1 2.419(3) 3_656 ?
N2 C2 1.305(6) . ?
N2 N3 1.374(6) . ?
C2 C8 1.450(7) . ?
N3 C3 1.326(6) . ?
C3 C4 1.448(7) . ?
C4 C5A 1.343(17) . ?
C4 C5B 1.366(18) . ?
C5A C7 1.46(2) . ?
C5A H5A 0.9300 . ?
C5B C6 1.46(2) . ?
C5B H5B 0.9300 . ?
C6 C7 1.337(8) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9A 1.256(9) . ?
C8 C9B 1.341(9) . ?
C8 C13B 1.405(8) . ?
C8 C13A 1.657(9) . ?
C9A C10A 1.373(14) . ?
C9A H9A 0.9300 . ?
C9B C10B 1.356(11) . ?
C9B H9B 0.9300 . ?
C10A C11A 1.350(14) . ?
C10A H10A 0.9300 . ?
C10B C11B 1.363(13) . ?
C10B H10B 0.9300 . ?
C11A C12A 1.381(12) . ?
C11A H11A 0.9300 . ?
C11B C12B 1.381(14) . ?
C11B H11B 0.9300 . ?
C12A C13A 1.419(10) . ?
C12A H12A 0.9300 . ?
C12B C13B 1.357(11) . ?
C12B H12B 0.9300 . ?
C13A H13A 0.9300 . ?
C13B H13B 0.9300 . ?
C14 C15 1.362(12) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 V1 O4 101.63(16) . . ?
O3 V1 O2 108.66(17) . . ?
O4 V1 O2 44.90(13) . . ?
O3 V1 O1 100.91(15) . . ?
O4 V1 O1 81.37(13) . . ?
O2 V1 O1 121.99(13) . . ?
O3 V1 N2 99.09(17) . . ?
O4 V1 N2 150.35(15) . . ?
O2 V1 N2 143.05(16) . . ?
O1 V1 N2 74.03(15) . . ?
O3 V1 N1 88.45(16) . . ?
O4 V1 N1 127.62(17) . . ?
O2 V1 N1 83.01(16) . . ?
O1 V1 N1 147.37(16) . . ?
N2 V1 N1 73.65(17) . . ?
O3 V1 O2 173.49(15) . 3_656 ?
O4 V1 O2 84.84(13) . 3_656 ?
O2 V1 O2 76.34(14) . 3_656 ?
O1 V1 O2 79.28(12) . 3_656 ?
N2 V1 O2 74.65(13) . 3_656 ?
N1 V1 O2 88.05(13) . 3_656 ?
C3 O1 V1 116.4(3) . . ?
C17 N1 C1 119.0(5) . . ?
C17 N1 V1 123.3(4) . . ?
C1 N1 V1 117.3(4) . . ?
N1 C1 C14 120.7(7) . . ?
N1 C1 C2 113.9(4) . . ?
C14 C1 C2 125.4(6) . . ?
C6 S1A C4 89.9(3) . . ?
C7 S1B C4 90.1(4) . . ?
O4 O2 V1 66.97(18) . . ?
O4 O2 V1 101.1(2) . 3_656 ?
V1 O2 V1 103.66(14) . 3_656 ?
C2 N2 N3 119.4(4) . . ?
C2 N2 V1 121.5(4) . . ?
N3 N2 V1 118.9(3) . . ?
N2 C2 C8 126.4(6) . . ?
N2 C2 C1 112.9(5) . . ?
C8 C2 C1 120.4(5) . . ?
C3 N3 N2 106.4(4) . . ?
O1 C3 N3 124.0(4) . . ?
O1 C3 C4 117.7(4) . . ?
N3 C3 C4 118.3(4) . . ?
O2 O4 V1 68.13(18) . . ?
C5A C4 C5B 101.4(14) . . ?
C5A C4 C3 129.6(10) . . ?
C5B C4 C3 128.9(10) . . ?
C5A C4 S1A 110.6(10) . . ?
C5B C4 S1A 9.4(10) . . ?
C3 C4 S1A 119.7(4) . . ?
C5A C4 S1B 9.7(10) . . ?
C5B C4 S1B 110.2(10) . . ?
C3 C4 S1B 120.7(4) . . ?
S1A C4 S1B 119.5(4) . . ?
C4 C5A C7 114.8(13) . . ?
C4 C5A H5A 122.6 . . ?
C7 C5A H5A 122.6 . . ?
C4 C5B C6 113.6(13) . . ?
C4 C5B H5B 123.2 . . ?
C6 C5B H5B 123.2 . . ?
C7 C6 C5B 105.2(8) . . ?
C7 C6 S1A 119.7(5) . . ?
C5B C6 S1A 14.6(7) . . ?
C7 C6 H6 120.2 . . ?
C5B C6 H6 134.6 . . ?
S1A C6 H6 120.2 . . ?
C6 C7 C5A 104.9(8) . . ?
C6 C7 S1B 120.6(5) . . ?
C5A C7 S1B 16.2(6) . . ?
C6 C7 H7 127.6 . . ?
C5A C7 H7 127.6 . . ?
S1B C7 H7 111.7 . . ?
C9A C8 C9B 55.1(4) . . ?
C9A C8 C13B 77.2(5) . . ?
C9B C8 C13B 122.7(7) . . ?
C9A C8 C2 137.5(7) . . ?
C9B C8 C2 119.4(5) . . ?
C13B C8 C2 117.1(5) . . ?
C9A C8 C13A 107.2(6) . . ?
C9B C8 C13A 92.0(4) . . ?
C13B C8 C13A 72.1(3) . . ?
C2 C8 C13A 115.3(5) . . ?
C8 C9A C10A 129.9(11) . . ?
C8 C9A H9A 115.1 . . ?
C10A C9A H9A 115.1 . . ?
C8 C9B C10B 119.1(8) . . ?
C8 C9B H9B 120.4 . . ?
C10B C9B H9B 120.4 . . ?
C11A C10A C9A 124.4(15) . . ?
C11A C10A H10A 117.8 . . ?
C9A C10A H10A 117.8 . . ?
C9B C10B C11B 120.6(12) . . ?
C9B C10B H10B 119.7 . . ?
C11B C10B H10B 119.7 . . ?
C10A C11A C12A 118.9(11) . . ?
C10A C11A H11A 120.6 . . ?
C12A C11A H11A 120.6 . . ?
C10B C11B C12B 119.8(15) . . ?
C10B C11B H11B 120.1 . . ?
C12B C11B H11B 120.1 . . ?
C11A C12A C13A 117.0(9) . . ?
C11A C12A H12A 121.5 . . ?
C13A C12A H12A 121.5 . . ?
C13B C12B C11B 121.1(11) . . ?
C13B C12B H12B 119.5 . . ?
C11B C12B H12B 119.5 . . ?
C12A C13A C8 122.6(7) . . ?
C12A C13A H13A 118.7 . . ?
C8 C13A H13A 118.7 . . ?
C12B C13B C8 116.7(8) . . ?
C12B C13B H13B 121.7 . . ?
C8 C13B H13B 121.7 . . ?
C15 C14 C1 119.8(7) . . ?
C15 C14 H14 120.1 . . ?
C1 C14 H14 120.1 . . ?
C14 C15 C16 120.2(6) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 117.9(7) . . ?
C15 C16 H16 121.0 . . ?
C17 C16 H16 121.0 . . ?
N1 C17 C16 122.4(6) . . ?
N1 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 V1 O1 C3 100.9(3) . . . . ?
O4 V1 O1 C3 -158.8(3) . . . . ?
O2 V1 O1 C3 -138.8(3) . . . . ?
N2 V1 O1 C3 4.5(3) . . . . ?
N1 V1 O1 C3 -3.6(5) . . . . ?
O2 V1 O1 C3 -72.5(3) 3_656 . . . ?
O3 V1 N1 C17 79.8(4) . . . . ?
O4 V1 N1 C17 -23.7(5) . . . . ?
O2 V1 N1 C17 -29.2(4) . . . . ?
O1 V1 N1 C17 -172.2(3) . . . . ?
N2 V1 N1 C17 179.7(4) . . . . ?
O2 V1 N1 C17 -105.7(4) 3_656 . . . ?
O3 V1 N1 C1 -92.7(4) . . . . ?
O4 V1 N1 C1 163.8(3) . . . . ?
O2 V1 N1 C1 158.3(4) . . . . ?
O1 V1 N1 C1 15.3(5) . . . . ?
N2 V1 N1 C1 7.2(3) . . . . ?
O2 V1 N1 C1 81.8(4) 3_656 . . . ?
C17 N1 C1 C14 -2.8(8) . . . . ?
V1 N1 C1 C14 170.0(4) . . . . ?
C17 N1 C1 C2 177.2(4) . . . . ?
V1 N1 C1 C2 -10.0(6) . . . . ?
O3 V1 O2 O4 87.9(2) . . . . ?
O1 V1 O2 O4 -28.7(2) . . . . ?
N2 V1 O2 O4 -135.6(2) . . . . ?
N1 V1 O2 O4 173.8(2) . . . . ?
O2 V1 O2 O4 -96.5(2) 3_656 . . . ?
O3 V1 O2 V1 -175.67(14) . . . 3_656 ?
O4 V1 O2 V1 96.5(2) . . . 3_656 ?
O1 V1 O2 V1 67.82(17) . . . 3_656 ?
N2 V1 O2 V1 -39.1(3) . . . 3_656 ?
N1 V1 O2 V1 -89.68(15) . . . 3_656 ?
O2 V1 O2 V1 0.0 3_656 . . 3_656 ?
O3 V1 N2 C2 82.3(4) . . . . ?
O4 V1 N2 C2 -143.8(4) . . . . ?
O2 V1 N2 C2 -56.5(5) . . . . ?
O1 V1 N2 C2 -178.9(4) . . . . ?
N1 V1 N2 C2 -3.4(4) . . . . ?
O2 V1 N2 C2 -95.9(4) 3_656 . . . ?
O3 V1 N2 N3 -102.0(3) . . . . ?
O4 V1 N2 N3 31.9(5) . . . . ?
O2 V1 N2 N3 119.2(4) . . . . ?
O1 V1 N2 N3 -3.2(3) . . . . ?
N1 V1 N2 N3 172.3(4) . . . . ?
O2 V1 N2 N3 79.8(3) 3_656 . . . ?
N3 N2 C2 C8 -2.0(8) . . . . ?
V1 N2 C2 C8 173.6(4) . . . . ?
N3 N2 C2 C1 -176.4(4) . . . . ?
V1 N2 C2 C1 -0.7(6) . . . . ?
N1 C1 C2 N2 6.9(7) . . . . ?
C14 C1 C2 N2 -173.1(5) . . . . ?
N1 C1 C2 C8 -167.8(4) . . . . ?
C14 C1 C2 C8 12.2(8) . . . . ?
C2 N2 N3 C3 177.1(4) . . . . ?
V1 N2 N3 C3 1.3(5) . . . . ?
V1 O1 C3 N3 -5.9(6) . . . . ?
V1 O1 C3 C4 172.1(3) . . . . ?
N2 N3 C3 O1 2.9(6) . . . . ?
N2 N3 C3 C4 -175.1(4) . . . . ?
V1 O2 O4 V1 -100.24(14) 3_656 . . . ?
O3 V1 O4 O2 -104.8(2) . . . . ?
O1 V1 O4 O2 155.7(2) . . . . ?
N2 V1 O4 O2 121.7(3) . . . . ?
N1 V1 O4 O2 -7.7(3) . . . . ?
O2 V1 O4 O2 75.8(2) 3_656 . . . ?
O1 C3 C4 C5A -170.1(17) . . . . ?
N3 C3 C4 C5A 8.1(18) . . . . ?
O1 C3 C4 C5B 8.6(18) . . . . ?
N3 C3 C4 C5B -173.2(17) . . . . ?
O1 C3 C4 S1A 11.1(6) . . . . ?
N3 C3 C4 S1A -170.7(4) . . . . ?
O1 C3 C4 S1B -165.4(5) . . . . ?
N3 C3 C4 S1B 12.7(7) . . . . ?
C6 S1A C4 C5A 1.5(14) . . . . ?
C6 S1A C4 C5B -11(9) . . . . ?
C6 S1A C4 C3 -179.4(4) . . . . ?
C6 S1A C4 S1B -2.8(6) . . . . ?
C7 S1B C4 C5A -21(9) . . . . ?
C7 S1B C4 C5B 5.3(16) . . . . ?
C7 S1B C4 C3 -179.6(5) . . . . ?
C7 S1B C4 S1A 3.9(7) . . . . ?
C5B C4 C5A C7 -1(3) . . . . ?
C3 C4 C5A C7 178.2(10) . . . . ?
S1A C4 C5A C7 -3(2) . . . . ?
S1B C4 C5A C7 154(11) . . . . ?
C5A C4 C5B C6 -2(2) . . . . ?
C3 C4 C5B C6 179.5(10) . . . . ?
S1A C4 C5B C6 166(11) . . . . ?
S1B C4 C5B C6 -6(2) . . . . ?
C4 C5B C6 C7 3(2) . . . . ?
C4 C5B C6 S1A -171(7) . . . . ?
C4 S1A C6 C7 0.2(7) . . . . ?
C4 S1A C6 C5B 7(5) . . . . ?
C5B C6 C7 C5A -3.4(19) . . . . ?
S1A C6 C7 C5A -1.7(15) . . . . ?
C5B C6 C7 S1B 1.0(15) . . . . ?
S1A C6 C7 S1B 2.7(11) . . . . ?
C4 C5A C7 C6 3(2) . . . . ?
C4 C5A C7 S1B -164(7) . . . . ?
C4 S1B C7 C6 -3.7(9) . . . . ?
C4 S1B C7 C5A 12(5) . . . . ?
N2 C2 C8 C9A -130.1(6) . . . . ?
C1 C2 C8 C9A 43.8(7) . . . . ?
N2 C2 C8 C9B -61.0(7) . . . . ?
C1 C2 C8 C9B 112.9(5) . . . . ?
N2 C2 C8 C13B 129.0(5) . . . . ?
C1 C2 C8 C13B -57.1(6) . . . . ?
N2 C2 C8 C13A 47.1(6) . . . . ?
C1 C2 C8 C13A -139.0(5) . . . . ?
C9B C8 C9A C10A 80.2(5) . . . . ?
C13B C8 C9A C10A -66.3(4) . . . . ?
C2 C8 C9A C10A 177.4(5) . . . . ?
C13A C8 C9A C10A 0.03(3) . . . . ?
C9A C8 C9B C10B -39.8(6) . . . . ?
C13B C8 C9B C10B -0.04(4) . . . . ?
C2 C8 C9B C10B -169.4(6) . . . . ?
C13A C8 C9B C10B 69.9(4) . . . . ?
C8 C9A C10A C11A 0.02(5) . . . . ?
C8 C9B C10B C11B -0.01(4) . . . . ?
C9A C10A C11A C12A -0.03(10) . . . . ?
C9B C10B C11B C12B 0.02(8) . . . . ?
C10A C11A C12A C13A -0.01(12) . . . . ?
C10B C11B C12B C13B 0.03(11) . . . . ?
C11A C12A C13A C8 0.06(12) . . . . ?
C9A C8 C13A C12A -0.07(9) . . . . ?
C9B C8 C13A C12A -54.1(5) . . . . ?
C13B C8 C13A C12A 69.8(5) . . . . ?
C2 C8 C13A C12A -178.1(4) . . . . ?
C11B C12B C13B C8 -0.08(11) . . . . ?
C9A C8 C13B C12B 32.6(5) . . . . ?
C9B C8 C13B C12B 0.08(8) . . . . ?
C2 C8 C13B C12B 169.7(5) . . . . ?
C13A C8 C13B C12B -80.5(4) . . . . ?
N1 C1 C14 C15 1.2(10) . . . . ?
C2 C1 C14 C15 -178.8(6) . . . . ?
C1 C14 C15 C16 1.0(11) . . . . ?
C14 C15 C16 C17 -1.5(10) . . . . ?
C1 N1 C17 C16 2.3(7) . . . . ?
V1 N1 C17 C16 -170.1(4) . . . . ?
C15 C16 C17 N1 -0.1(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.45
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.820
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.087
_database_code_depnum_ccdc_archive 'CCDC 1018365'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_manar196

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 N4 O5 V, 0.5(C H4 O)'
_chemical_formula_sum            'C18.50 H17 N4 O5.50 V'
_chemical_formula_weight         434.30

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'
V V 0.3005 0.5294 '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
_symmetry_space_group_name_Hall  -P2ybc

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                   10.2637(12)
_cell_length_b                   22.806(3)
_cell_length_c                   8.1173(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.364(7)
_cell_angle_gamma                90.00
_cell_volume                     1832.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    34859
_cell_measurement_theta_min      4.485
_cell_measurement_theta_max      31.241

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             892
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9226
_exptl_absorpt_correction_T_max  0.9602
_exptl_absorpt_process_details   'North et al., 1968'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            34088
_diffrn_reflns_av_R_equivalents  0.1672
_diffrn_reflns_av_sigmaI/netI    0.1090
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         26.52
_reflns_number_total             3757
_reflns_number_gt                2188
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
' SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite.'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS Version 2008/1 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122) '
_computing_structure_refinement  
'XL Version 2008/4 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1087P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3757
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1257
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.2028
_refine_ls_wR_factor_gt          0.1601
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
V1 V 0.38380(8) 0.61361(4) 0.42778(10) 0.0234(3) Uani 1 1 d . . .
O1 O 0.2787(3) 0.58245(14) 0.1980(4) 0.0244(8) Uani 1 1 d . . .
N1 N 0.3725(4) 0.64997(17) 0.6676(5) 0.0246(9) Uani 1 1 d . . .
C1 C 0.2510(5) 0.6705(2) 0.6781(6) 0.0235(11) Uani 1 1 d . . .
N2 N 0.1809(4) 0.63796(17) 0.3997(5) 0.0221(9) Uani 1 1 d . . .
O2 O 0.3027(3) 0.53492(14) 0.5368(4) 0.0244(8) Uani 1 1 d . . .
C2 C 0.1418(5) 0.6645(2) 0.5193(6) 0.0248(11) Uani 1 1 d . . .
O3 O 0.4215(3) 0.67583(14) 0.3638(4) 0.0260(8) Uani 1 1 d . . .
N3 N 0.0906(4) 0.62732(17) 0.2448(5) 0.0228(9) Uani 1 1 d . . .
C3 C 0.1529(5) 0.5968(2) 0.1525(6) 0.0246(11) Uani 1 1 d . . .
O4 O 0.5168(3) 0.56304(15) 0.3890(4) 0.0276(8) Uani 1 1 d . . .
N4 N -0.0931(4) 0.52627(18) -0.3155(5) 0.0268(10) Uani 1 1 d . . .
C4 C 0.0681(5) 0.5759(2) -0.0163(6) 0.0228(10) Uani 1 1 d . . .
O5 O 0.5477(3) 0.58554(15) 0.5606(4) 0.0290(8) Uani 1 1 d . . .
C5 C 0.1241(5) 0.5483(2) -0.1331(6) 0.0258(11) Uani 1 1 d . . .
H5 H 0.2194 0.5459 -0.1131 0.031 Uiso 1 1 calc R . .
C6 C 0.0405(5) 0.5243(2) -0.2779(6) 0.0280(12) Uani 1 1 d . . .
H6 H 0.0809 0.5052 -0.3560 0.034 Uiso 1 1 calc R . .
C7 C -0.1470(5) 0.5544(2) -0.2039(6) 0.0304(12) Uani 1 1 d . . .
H7 H -0.236(5) 0.559(2) -0.234(6) 0.028(14) Uiso 1 1 d . . .
C8 C -0.0709(5) 0.5794(2) -0.0538(6) 0.0274(11) Uani 1 1 d . . .
H8 H -0.110(5) 0.602(2) 0.026(6) 0.034(14) Uiso 1 1 d . . .
C9 C 0.0029(5) 0.6847(2) 0.5051(6) 0.0240(11) Uani 1 1 d . . .
C10 C -0.0217(5) 0.7413(2) 0.5543(6) 0.0295(12) Uani 1 1 d . . .
H10 H 0.050(4) 0.7690(19) 0.586(5) 0.013(11) Uiso 1 1 d . . .
C11 C -0.1526(5) 0.7592(2) 0.5448(7) 0.0367(13) Uani 1 1 d . . .
H11 H -0.147(6) 0.802(3) 0.587(8) 0.061(19) Uiso 1 1 d . . .
C12 C -0.2582(6) 0.7210(3) 0.4841(8) 0.0413(15) Uani 1 1 d . . .
H12 H -0.329(5) 0.733(2) 0.479(6) 0.028(15) Uiso 1 1 d . . .
C13 C -0.2357(5) 0.6653(3) 0.4349(7) 0.0327(13) Uani 1 1 d . . .
H13 H -0.300(5) 0.641(2) 0.396(6) 0.035(16) Uiso 1 1 d . . .
C14 C -0.1057(4) 0.6469(2) 0.4424(6) 0.0264(11) Uani 1 1 d . . .
H14 H -0.0906 0.6087 0.4048 0.032 Uiso 1 1 calc R . .
C15 C 0.2320(5) 0.6921(2) 0.8305(6) 0.0288(12) Uani 1 1 d . . .
H15 H 0.132(5) 0.705(2) 0.832(6) 0.034(14) Uiso 1 1 d . . .
C16 C 0.3396(5) 0.6936(2) 0.9733(7) 0.0313(12) Uani 1 1 d . . .
H16 H 0.3289 0.7081 1.0786 0.038 Uiso 1 1 calc R . .
C17 C 0.4638(6) 0.6735(2) 0.9611(7) 0.0333(13) Uani 1 1 d . . .
H17 H 0.541(5) 0.672(2) 1.057(6) 0.035(14) Uiso 1 1 d . . .
C18 C 0.4760(4) 0.6520(2) 0.8078(6) 0.0313(12) Uani 1 1 d . . .
H18 H 0.5616 0.6380 0.8013 0.038 Uiso 1 1 calc R . .
H2OA H 0.2168 0.5171 0.4582 0.038 Uiso 1 1 d R . .
H2OB H 0.3700 0.5021 0.5524 0.038 Uiso 1 1 d R . .
O1M O 0.3631(4) 0.4430(2) -0.1025(6) 0.074(3) Uiso 0.50 1 d PR A -1
H1M H 0.3525 0.4144 -0.0421 0.111 Uiso 0.50 1 calc PR B -1
C1M C 0.4660(12) 0.4838(5) 0.0024(17) 0.048(3) Uiso 0.50 1 d P A -1
H1M1 H 0.4725 0.5189 -0.0649 0.072 Uiso 0.50 1 calc PR A -1
H1M2 H 0.5540 0.4642 0.0358 0.072 Uiso 0.50 1 calc PR A -1
H1M3 H 0.4390 0.4952 0.1050 0.072 Uiso 0.50 1 calc PR A -1


_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
V1 O3 1.593(3) . ?
V1 O5 1.855(3) . ?
V1 O4 1.876(3) . ?
V1 O1 2.021(3) . ?
V1 N2 2.108(4) . ?
V1 N1 2.147(4) . ?
V1 O2 2.256(3) . ?
O1 C3 1.288(5) . ?
N1 C18 1.336(5) . ?
N1 C1 1.356(6) . ?
C1 C15 1.393(7) . ?
C1 C2 1.473(6) . ?
N2 C2 1.295(6) . ?
N2 N3 1.372(5) . ?
O2 H2OA 1.0253 . ?
O2 H2OB 1.0044 . ?
C2 C9 1.473(7) . ?
N3 C3 1.307(6) . ?
C3 C4 1.494(6) . ?
O4 O5 1.439(4) . ?
N4 C6 1.324(6) . ?
N4 C7 1.343(6) . ?
C4 C8 1.379(6) . ?
C4 C5 1.384(7) . ?
C5 C6 1.372(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.385(7) . ?
C7 H7 0.89(5) . ?
C8 H8 0.99(5) . ?
C9 C10 1.393(7) . ?
C9 C14 1.395(6) . ?
C10 C11 1.387(7) . ?
C10 H10 0.95(4) . ?
C11 C12 1.376(8) . ?
C11 H11 1.02(6) . ?
C12 C13 1.369(8) . ?
C12 H12 0.77(5) . ?
C13 C14 1.384(7) . ?
C13 H13 0.86(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(7) . ?
C15 H15 1.07(5) . ?
C16 C17 1.382(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.373(7) . ?
C17 H17 0.95(5) . ?
C18 H18 0.9500 . ?
O1M C1M 1.493(12) . ?
O1M H1M 0.8400 . ?
C1M H1M1 0.9800 . ?
C1M H1M2 0.9800 . ?
C1M H1M3 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
O3 V1 O5 103.64(16) . . ?
O3 V1 O4 104.05(16) . . ?
O5 V1 O4 45.36(13) . . ?
O3 V1 O1 97.40(15) . . ?
O5 V1 O1 126.54(14) . . ?
O4 V1 O1 82.13(13) . . ?
O3 V1 N2 92.76(16) . . ?
O5 V1 N2 150.60(15) . . ?
O4 V1 N2 152.30(15) . . ?
O1 V1 N2 73.89(13) . . ?
O3 V1 N1 91.57(15) . . ?
O5 V1 N1 82.23(14) . . ?
O4 V1 N1 127.30(14) . . ?
O1 V1 N1 146.00(14) . . ?
N2 V1 N1 72.97(14) . . ?
O3 V1 O2 169.43(15) . . ?
O5 V1 O2 82.50(13) . . ?
O4 V1 O2 86.40(13) . . ?
O1 V1 O2 85.42(12) . . ?
N2 V1 O2 78.18(13) . . ?
N1 V1 O2 80.64(13) . . ?
C3 O1 V1 115.1(3) . . ?
C18 N1 C1 118.1(4) . . ?
C18 N1 V1 124.4(3) . . ?
C1 N1 V1 117.5(3) . . ?
N1 C1 C15 121.7(4) . . ?
N1 C1 C2 114.3(4) . . ?
C15 C1 C2 123.9(4) . . ?
C2 N2 N3 120.1(4) . . ?
C2 N2 V1 122.4(3) . . ?
N3 N2 V1 117.4(3) . . ?
V1 O2 H2OA 114.7 . . ?
V1 O2 H2OB 109.3 . . ?
H2OA O2 H2OB 103.4 . . ?
N2 C2 C9 125.0(4) . . ?
N2 C2 C1 112.6(4) . . ?
C9 C2 C1 122.4(4) . . ?
C3 N3 N2 107.8(4) . . ?
O1 C3 N3 125.2(4) . . ?
O1 C3 C4 118.5(4) . . ?
N3 C3 C4 116.2(4) . . ?
O5 O4 V1 66.54(18) . . ?
C6 N4 C7 116.6(4) . . ?
C8 C4 C5 117.9(4) . . ?
C8 C4 C3 120.1(4) . . ?
C5 C4 C3 121.8(4) . . ?
O4 O5 V1 68.10(18) . . ?
C6 C5 C4 119.3(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
N4 C6 C5 123.9(5) . . ?
N4 C6 H6 118.0 . . ?
C5 C6 H6 118.0 . . ?
N4 C7 C8 123.6(5) . . ?
N4 C7 H7 117(3) . . ?
C8 C7 H7 120(3) . . ?
C4 C8 C7 118.7(5) . . ?
C4 C8 H8 117(3) . . ?
C7 C8 H8 124(3) . . ?
C10 C9 C14 119.3(5) . . ?
C10 C9 C2 120.8(4) . . ?
C14 C9 C2 120.0(4) . . ?
C11 C10 C9 120.2(5) . . ?
C11 C10 H10 119(3) . . ?
C9 C10 H10 120(3) . . ?
C12 C11 C10 119.5(5) . . ?
C12 C11 H11 134(3) . . ?
C10 C11 H11 107(3) . . ?
C13 C12 C11 120.9(5) . . ?
C13 C12 H12 124(4) . . ?
C11 C12 H12 115(4) . . ?
C12 C13 C14 120.2(5) . . ?
C12 C13 H13 123(4) . . ?
C14 C13 H13 117(4) . . ?
C13 C14 C9 119.8(5) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
C16 C15 C1 119.2(5) . . ?
C16 C15 H15 123(3) . . ?
C1 C15 H15 118(3) . . ?
C15 C16 C17 118.8(5) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C18 C17 C16 119.4(5) . . ?
C18 C17 H17 118(3) . . ?
C16 C17 H17 122(3) . . ?
N1 C18 C17 122.8(4) . . ?
N1 C18 H18 118.6 . . ?
C17 C18 H18 118.6 . . ?

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
O3 V1 O1 C3 -85.9(3) . . . . ?
O5 V1 O1 C3 161.0(3) . . . . ?
O4 V1 O1 C3 170.8(3) . . . . ?
N2 V1 O1 C3 4.8(3) . . . . ?
N1 V1 O1 C3 18.1(5) . . . . ?
O2 V1 O1 C3 83.8(3) . . . . ?
O3 V1 N1 C18 -91.7(4) . . . . ?
O5 V1 N1 C18 11.9(4) . . . . ?
O4 V1 N1 C18 17.4(4) . . . . ?
O1 V1 N1 C18 162.6(3) . . . . ?
N2 V1 N1 C18 175.9(4) . . . . ?
O2 V1 N1 C18 95.5(4) . . . . ?
O3 V1 N1 C1 90.4(3) . . . . ?
O5 V1 N1 C1 -166.0(4) . . . . ?
O4 V1 N1 C1 -160.5(3) . . . . ?
O1 V1 N1 C1 -15.3(5) . . . . ?
N2 V1 N1 C1 -2.0(3) . . . . ?
O2 V1 N1 C1 -82.4(3) . . . . ?
C18 N1 C1 C15 -1.4(7) . . . . ?
V1 N1 C1 C15 176.6(4) . . . . ?
C18 N1 C1 C2 -177.9(4) . . . . ?
V1 N1 C1 C2 0.2(5) . . . . ?
O3 V1 N2 C2 -86.7(4) . . . . ?
O5 V1 N2 C2 37.8(6) . . . . ?
O4 V1 N2 C2 145.3(4) . . . . ?
O1 V1 N2 C2 176.4(4) . . . . ?
N1 V1 N2 C2 4.1(4) . . . . ?
O2 V1 N2 C2 87.8(4) . . . . ?
O3 V1 N2 N3 90.0(3) . . . . ?
O5 V1 N2 N3 -145.5(3) . . . . ?
O4 V1 N2 N3 -37.9(5) . . . . ?
O1 V1 N2 N3 -6.9(3) . . . . ?
N1 V1 N2 N3 -179.2(3) . . . . ?
O2 V1 N2 N3 -95.5(3) . . . . ?
N3 N2 C2 C9 0.8(7) . . . . ?
V1 N2 C2 C9 177.5(3) . . . . ?
N3 N2 C2 C1 178.2(4) . . . . ?
V1 N2 C2 C1 -5.2(6) . . . . ?
N1 C1 C2 N2 3.0(6) . . . . ?
C15 C1 C2 N2 -173.3(4) . . . . ?
N1 C1 C2 C9 -179.5(4) . . . . ?
C15 C1 C2 C9 4.1(7) . . . . ?
C2 N2 N3 C3 -175.8(4) . . . . ?
V1 N2 N3 C3 7.4(5) . . . . ?
V1 O1 C3 N3 -2.5(6) . . . . ?
V1 O1 C3 C4 179.6(3) . . . . ?
N2 N3 C3 O1 -3.3(6) . . . . ?
N2 N3 C3 C4 174.6(4) . . . . ?
O3 V1 O4 O5 95.4(2) . . . . ?
O1 V1 O4 O5 -168.9(2) . . . . ?
N2 V1 O4 O5 -138.9(3) . . . . ?
N1 V1 O4 O5 -7.7(3) . . . . ?
O2 V1 O4 O5 -83.01(19) . . . . ?
O1 C3 C4 C8 166.1(4) . . . . ?
N3 C3 C4 C8 -12.0(7) . . . . ?
O1 C3 C4 C5 -8.4(7) . . . . ?
N3 C3 C4 C5 173.5(4) . . . . ?
O3 V1 O5 O4 -96.4(2) . . . . ?
O1 V1 O5 O4 13.8(3) . . . . ?
N2 V1 O5 O4 141.5(3) . . . . ?
N1 V1 O5 O4 173.9(2) . . . . ?
O2 V1 O5 O4 92.3(2) . . . . ?
C8 C4 C5 C6 -1.6(7) . . . . ?
C3 C4 C5 C6 173.0(4) . . . . ?
C7 N4 C6 C5 1.0(7) . . . . ?
C4 C5 C6 N4 0.6(8) . . . . ?
C6 N4 C7 C8 -1.6(7) . . . . ?
C5 C4 C8 C7 1.0(7) . . . . ?
C3 C4 C8 C7 -173.7(5) . . . . ?
N4 C7 C8 C4 0.6(8) . . . . ?
N2 C2 C9 C10 -131.9(5) . . . . ?
C1 C2 C9 C10 51.0(7) . . . . ?
N2 C2 C9 C14 48.3(7) . . . . ?
C1 C2 C9 C14 -128.8(5) . . . . ?
C14 C9 C10 C11 1.6(7) . . . . ?
C2 C9 C10 C11 -178.2(5) . . . . ?
C9 C10 C11 C12 -1.0(8) . . . . ?
C10 C11 C12 C13 0.9(9) . . . . ?
C11 C12 C13 C14 -1.4(9) . . . . ?
C12 C13 C14 C9 2.0(8) . . . . ?
C10 C9 C14 C13 -2.1(7) . . . . ?
C2 C9 C14 C13 177.7(4) . . . . ?
N1 C1 C15 C16 1.2(7) . . . . ?
C2 C1 C15 C16 177.3(4) . . . . ?
C1 C15 C16 C17 0.0(7) . . . . ?
C15 C16 C17 C18 -0.8(8) . . . . ?
C1 N1 C18 C17 0.5(7) . . . . ?
V1 N1 C18 C17 -177.3(4) . . . . ?
C16 C17 C18 N1 0.6(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2OA N4 1.03 1.78 2.784(5) 167.2 3_565
O2 H2OB O4 1.00 1.87 2.863(4) 170.5 3_666
O2 H2OB O5 1.00 2.44 3.343(5) 149.1 3_666

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.123
_database_code_depnum_ccdc_archive 'CCDC 1018366'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_manar195

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 N3 O3 S V'
_chemical_formula_sum            'C17 H12 N3 O3 S V'
_chemical_formula_weight         389.30

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'
V V 0.3005 0.5294 '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  -P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3281(6)
_cell_length_b                   9.6580(8)
_cell_length_c                   22.010(2)
_cell_angle_alpha                81.235(6)
_cell_angle_beta                 87.348(6)
_cell_angle_gamma                68.383(5)
_cell_volume                     1626.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    55712
_cell_measurement_theta_min      4.581
_cell_measurement_theta_max      40.962

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8506
_exptl_absorpt_correction_T_max  0.9558
_exptl_absorpt_process_details   'North et al., 1968'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            55659
_diffrn_reflns_av_R_equivalents  0.1076
_diffrn_reflns_av_sigmaI/netI    0.0716
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         0.94
_diffrn_reflns_theta_max         27.57
_reflns_number_total             7484
_reflns_number_gt                5018
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
' SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite.'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS Version 2008/1 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122) '
_computing_structure_refinement  
'XL Version 2008/4 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0811P)²+0.2192P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7484
_refine_ls_number_parameters     547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
V1 V 0.44391(7) 0.46555(6) 0.93814(3) 0.01891(15) Uani 1 1 d . . .
S1 S -0.13736(12) 0.98189(10) 0.88814(5) 0.0291(2) Uani 1 1 d . . .
O1 O 0.2005(3) 0.5822(2) 0.95151(10) 0.0207(5) Uani 1 1 d . . .
N1 N 0.6807(3) 0.4664(3) 0.90071(12) 0.0195(6) Uani 1 1 d . . .
C1 C 0.6812(4) 0.5859(4) 0.85995(15) 0.0191(7) Uani 1 1 d . . .
V2 V 0.64157(7) 0.84381(6) 0.49063(3) 0.01940(16) Uani 1 1 d . . .
S2 S 0.98934(12) 0.81542(11) 0.70260(4) 0.0274(2) Uani 1 1 d . . .
O2 O 0.5171(3) 0.3607(3) 1.00506(10) 0.0230(5) Uani 1 1 d . . .
N2 N 0.3882(3) 0.6701(3) 0.87728(12) 0.0188(6) Uani 1 1 d . . .
C2 C 0.5091(4) 0.7046(4) 0.84686(14) 0.0187(7) Uani 1 1 d . . .
O3 O 0.4181(3) 0.3569(2) 0.89375(10) 0.0218(5) Uani 1 1 d . . .
N3 N 0.2194(3) 0.7679(3) 0.87377(12) 0.0203(6) Uani 1 1 d . . .
C3 C 0.1339(4) 0.7117(4) 0.91585(15) 0.0212(7) Uani 1 1 d . . .
O4 O 0.8201(3) 0.8828(3) 0.53263(10) 0.0214(5) Uani 1 1 d . . .
N4 N 0.4474(3) 0.7507(3) 0.50010(12) 0.0196(6) Uani 1 1 d . . .
C4 C -0.0464(4) 0.7994(4) 0.92469(15) 0.0206(7) Uani 1 1 d . . .
O5 O 0.7647(3) 0.7249(3) 0.44834(11) 0.0261(5) Uani 1 1 d . . .
N5 N 0.6805(3) 0.7066(3) 0.57772(12) 0.0201(6) Uani 1 1 d . . .
C5 C -0.1640(4) 0.7571(4) 0.96094(16) 0.0222(7) Uani 1 1 d . . .
H5 H -0.138(5) 0.660(5) 0.9870(19) 0.042(12) Uiso 1 1 d . . .
O6 O 0.5393(3) 1.0013(2) 0.44343(10) 0.0208(5) Uani 1 1 d . . .
N6 N 0.7998(4) 0.7145(3) 0.61708(12) 0.0211(6) Uani 1 1 d . . .
C6 C -0.3275(5) 0.8739(4) 0.95950(17) 0.0251(8) Uani 1 1 d . . .
H6 H -0.425(5) 0.876(4) 0.9814(18) 0.039(12) Uiso 1 1 d . . .
C7 C -0.3310(5) 1.0025(4) 0.92250(18) 0.0294(8) Uani 1 1 d . . .
H7 H -0.424(6) 1.096(5) 0.9162(19) 0.046(12) Uiso 1 1 d . . .
C8 C 0.4816(4) 0.8475(4) 0.80576(15) 0.0182(7) Uani 1 1 d . . .
C9 C 0.3836(5) 0.9842(4) 0.82573(17) 0.0241(8) Uani 1 1 d . . .
H9 H 0.346(5) 0.986(4) 0.8664(19) 0.035(11) Uiso 1 1 d . . .
C10 C 0.3586(5) 1.1173(4) 0.78683(17) 0.0283(8) Uani 1 1 d . . .
H10 H 0.291(5) 1.218(5) 0.8038(19) 0.043(12) Uiso 1 1 d . . .
C11 C 0.4249(5) 1.1159(4) 0.72797(17) 0.0278(8) Uani 1 1 d . . .
H11 H 0.402(5) 1.209(4) 0.7038(17) 0.032(10) Uiso 1 1 d . . .
C12 C 0.5198(5) 0.9814(4) 0.70797(16) 0.0252(8) Uani 1 1 d . . .
H12 H 0.568(4) 0.982(4) 0.6672(15) 0.013(8) Uiso 1 1 d . . .
C13 C 0.5491(4) 0.8476(4) 0.74666(15) 0.0215(7) Uani 1 1 d . . .
H13 H 0.608(4) 0.758(4) 0.7329(15) 0.016(9) Uiso 1 1 d . . .
C14 C 0.8335(5) 0.5952(4) 0.83582(16) 0.0236(8) Uani 1 1 d . . .
H14 H 0.836(4) 0.677(4) 0.8083(14) 0.010(8) Uiso 1 1 d . . .
C15 C 0.9884(5) 0.4776(4) 0.85144(16) 0.0247(8) Uani 1 1 d . . .
H15 H 1.103(5) 0.486(4) 0.8342(17) 0.036(11) Uiso 1 1 d . . .
C16 C 0.9868(5) 0.3539(4) 0.89245(16) 0.0263(8) Uani 1 1 d . . .
H16 H 1.094(4) 0.266(4) 0.9058(15) 0.018(9) Uiso 1 1 d . . .
C17 C 0.8314(5) 0.3528(4) 0.91650(16) 0.0244(8) Uani 1 1 d . . .
H17 H 0.831(5) 0.272(4) 0.9448(17) 0.031(11) Uiso 1 1 d . . .
C18 C 0.4512(4) 0.6496(3) 0.55074(15) 0.0194(7) Uani 1 1 d . . .
C19 C 0.5866(4) 0.6267(4) 0.59614(15) 0.0201(7) Uani 1 1 d . . .
C20 C 0.8602(4) 0.8152(4) 0.58888(15) 0.0216(7) Uani 1 1 d . . .
C21 C 0.9742(4) 0.8580(4) 0.62370(15) 0.0211(7) Uani 1 1 d . . .
C22 C 1.0696(4) 0.9433(4) 0.60188(17) 0.0224(7) Uani 1 1 d . . .
H22 H 1.079(5) 0.973(4) 0.5617(17) 0.026(10) Uiso 1 1 d . . .
C23 C 1.1538(5) 0.9747(4) 0.64897(17) 0.0260(8) Uani 1 1 d . . .
H23 H 1.219(4) 1.032(4) 0.6455(14) 0.011(8) Uiso 1 1 d . . .
C24 C 1.1209(5) 0.9139(4) 0.70572(17) 0.0276(8) Uani 1 1 d . . .
H24 H 1.167(5) 0.918(4) 0.7423(17) 0.025(10) Uiso 1 1 d . . .
C25 C 0.6053(5) 0.5300(4) 0.65603(15) 0.0224(7) Uani 1 1 d . . .
C26 C 0.7679(5) 0.4236(4) 0.67525(17) 0.0250(8) Uani 1 1 d . . .
H26 H 0.864(4) 0.415(4) 0.6514(15) 0.017(9) Uiso 1 1 d . . .
C27 C 0.7840(6) 0.3300(4) 0.73080(17) 0.0319(9) Uani 1 1 d . . .
H27 H 0.897(5) 0.258(4) 0.7437(17) 0.032(11) Uiso 1 1 d . . .
C28 C 0.6433(6) 0.3443(4) 0.76793(17) 0.0320(9) Uani 1 1 d . . .
H28 H 0.659(5) 0.283(4) 0.8055(18) 0.031(10) Uiso 1 1 d . . .
C29 C 0.4833(6) 0.4525(4) 0.74996(17) 0.0315(9) Uani 1 1 d . . .
H29 H 0.389(5) 0.458(4) 0.7778(16) 0.022(9) Uiso 1 1 d . . .
C30 C 0.4643(5) 0.5442(4) 0.69398(16) 0.0253(8) Uani 1 1 d . . .
H30 H 0.355(6) 0.623(6) 0.685(2) 0.066(16) Uiso 1 1 d . . .
C31 C 0.3354(5) 0.5755(4) 0.55701(17) 0.0223(7) Uani 1 1 d . . .
H31 H 0.341(4) 0.514(4) 0.5870(15) 0.013(9) Uiso 1 1 d . . .
C32 C 0.2079(5) 0.6109(4) 0.51301(17) 0.0246(8) Uani 1 1 d . . .
H32 H 0.124(4) 0.557(4) 0.5196(14) 0.013(8) Uiso 1 1 d . . .
C33 C 0.2026(5) 0.7154(4) 0.46253(18) 0.0263(8) Uani 1 1 d . . .
H33 H 0.125(5) 0.744(4) 0.4314(17) 0.028(10) Uiso 1 1 d . . .
C34 C 0.3260(4) 0.7821(4) 0.45664(16) 0.0219(7) Uani 1 1 d . . .
H34 H 0.328(4) 0.858(3) 0.4212(14) 0.009(8) Uiso 1 1 d . . .


_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
V1 O3 1.613(2) . ?
V1 O2 1.655(2) . ?
V1 O1 1.956(2) . ?
V1 N1 2.104(3) . ?
V1 N2 2.119(3) . ?
V1 O2 2.358(2) 2_667 ?
S1 C7 1.706(4) . ?
S1 C4 1.723(3) . ?
O1 C3 1.311(4) . ?
N1 C17 1.345(4) . ?
N1 C1 1.351(4) . ?
C1 C14 1.381(5) . ?
C1 C2 1.476(5) . ?
V2 O5 1.615(2) . ?
V2 O6 1.662(2) . ?
V2 O4 1.963(2) . ?
V2 N4 2.110(3) . ?
V2 N5 2.122(3) . ?
V2 O6 2.327(2) 2_676 ?
S2 C24 1.704(4) . ?
S2 C21 1.722(3) . ?
O2 V1 2.358(2) 2_667 ?
N2 C2 1.300(4) . ?
N2 N3 1.372(4) . ?
C2 C8 1.477(4) . ?
N3 C3 1.315(4) . ?
C3 C4 1.448(5) . ?
O4 C20 1.305(4) . ?
N4 C34 1.343(4) . ?
N4 C18 1.358(4) . ?
C4 C5 1.373(5) . ?
N5 C19 1.300(4) . ?
N5 N6 1.378(4) . ?
C5 C6 1.410(5) . ?
C5 H5 0.98(4) . ?
O6 V2 2.327(2) 2_676 ?
N6 C20 1.315(4) . ?
C6 C7 1.369(5) . ?
C6 H6 0.92(4) . ?
C7 H7 0.95(4) . ?
C8 C13 1.393(5) . ?
C8 C9 1.397(5) . ?
C9 C10 1.383(5) . ?
C9 H9 0.94(4) . ?
C10 C11 1.385(5) . ?
C10 H10 1.05(4) . ?
C11 C12 1.375(5) . ?
C11 H11 0.93(4) . ?
C12 C13 1.381(5) . ?
C12 H12 0.96(3) . ?
C13 H13 0.92(3) . ?
C14 C15 1.384(5) . ?
C14 H14 0.92(3) . ?
C15 C16 1.387(5) . ?
C15 H15 1.04(4) . ?
C16 C17 1.379(5) . ?
C16 H16 0.99(3) . ?
C17 H17 0.92(4) . ?
C18 C31 1.388(5) . ?
C18 C19 1.474(4) . ?
C19 C25 1.473(4) . ?
C20 C21 1.454(5) . ?
C21 C22 1.367(5) . ?
C22 C23 1.406(5) . ?
C22 H22 0.90(4) . ?
C23 C24 1.358(5) . ?
C23 H23 0.89(3) . ?
C24 H24 0.92(4) . ?
C25 C30 1.386(5) . ?
C25 C26 1.401(5) . ?
C26 C27 1.385(5) . ?
C26 H26 0.92(3) . ?
C27 C28 1.374(6) . ?
C27 H27 0.97(4) . ?
C28 C29 1.386(6) . ?
C28 H28 0.93(4) . ?
C29 C30 1.382(5) . ?
C29 H29 0.96(4) . ?
C30 H30 0.95(5) . ?
C31 C32 1.381(5) . ?
C31 H31 0.81(3) . ?
C32 C33 1.373(5) . ?
C32 H32 1.01(3) . ?
C33 C34 1.393(5) . ?
C33 H33 0.90(4) . ?
C34 H34 0.99(3) . ?

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
O3 V1 O2 107.21(12) . . ?
O3 V1 O1 98.48(11) . . ?
O2 V1 O1 105.34(11) . . ?
O3 V1 N1 95.78(11) . . ?
O2 V1 N1 98.47(11) . . ?
O1 V1 N1 147.06(10) . . ?
O3 V1 N2 101.60(11) . . ?
O2 V1 N2 150.73(11) . . ?
O1 V1 N2 74.86(10) . . ?
N1 V1 N2 73.26(10) . . ?
O3 V1 O2 174.81(10) . 2_667 ?
O2 V1 O2 77.63(11) . 2_667 ?
O1 V1 O2 81.79(9) . 2_667 ?
N1 V1 O2 81.46(9) . 2_667 ?
N2 V1 O2 73.42(9) . 2_667 ?
C7 S1 C4 91.43(17) . . ?
C3 O1 V1 116.1(2) . . ?
C17 N1 C1 119.0(3) . . ?
C17 N1 V1 122.2(2) . . ?
C1 N1 V1 118.8(2) . . ?
N1 C1 C14 121.2(3) . . ?
N1 C1 C2 114.3(3) . . ?
C14 C1 C2 124.4(3) . . ?
O5 V2 O6 106.55(12) . . ?
O5 V2 O4 98.91(11) . . ?
O6 V2 O4 105.87(10) . . ?
O5 V2 N4 95.11(11) . . ?
O6 V2 N4 99.38(11) . . ?
O4 V2 N4 146.09(10) . . ?
O5 V2 N5 100.73(12) . . ?
O6 V2 N5 152.29(11) . . ?
O4 V2 N5 74.06(10) . . ?
N4 V2 N5 73.07(10) . . ?
O5 V2 O6 175.32(10) . 2_676 ?
O6 V2 O6 77.28(10) . 2_676 ?
O4 V2 O6 82.39(9) . 2_676 ?
N4 V2 O6 81.49(9) . 2_676 ?
N5 V2 O6 75.25(9) . 2_676 ?
C24 S2 C21 91.57(17) . . ?
V1 O2 V1 102.37(11) . 2_667 ?
C2 N2 N3 121.5(3) . . ?
C2 N2 V1 121.7(2) . . ?
N3 N2 V1 116.78(19) . . ?
N2 C2 C1 112.0(3) . . ?
N2 C2 C8 124.8(3) . . ?
C1 C2 C8 123.1(3) . . ?
C3 N3 N2 107.2(3) . . ?
O1 C3 N3 124.8(3) . . ?
O1 C3 C4 116.9(3) . . ?
N3 C3 C4 118.3(3) . . ?
C20 O4 V2 117.0(2) . . ?
C34 N4 C18 119.1(3) . . ?
C34 N4 V2 122.4(2) . . ?
C18 N4 V2 118.4(2) . . ?
C5 C4 C3 128.1(3) . . ?
C5 C4 S1 111.6(3) . . ?
C3 C4 S1 120.3(2) . . ?
C19 N5 N6 120.1(3) . . ?
C19 N5 V2 122.1(2) . . ?
N6 N5 V2 117.59(19) . . ?
C4 C5 C6 112.3(3) . . ?
C4 C5 H5 125(2) . . ?
C6 C5 H5 123(2) . . ?
V2 O6 V2 102.72(10) . 2_676 ?
C20 N6 N5 106.6(3) . . ?
C7 C6 C5 112.4(3) . . ?
C7 C6 H6 118(3) . . ?
C5 C6 H6 129(3) . . ?
C6 C7 S1 112.2(3) . . ?
C6 C7 H7 127(3) . . ?
S1 C7 H7 120(3) . . ?
C13 C8 C9 119.5(3) . . ?
C13 C8 C2 120.7(3) . . ?
C9 C8 C2 119.8(3) . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120(2) . . ?
C8 C9 H9 120(2) . . ?
C9 C10 C11 120.7(4) . . ?
C9 C10 H10 118(2) . . ?
C11 C10 H10 121(2) . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 123(2) . . ?
C10 C11 H11 117(2) . . ?
C11 C12 C13 119.9(3) . . ?
C11 C12 H12 119.4(19) . . ?
C13 C12 H12 120.7(19) . . ?
C12 C13 C8 120.5(3) . . ?
C12 C13 H13 120(2) . . ?
C8 C13 H13 119(2) . . ?
C1 C14 C15 119.8(3) . . ?
C1 C14 H14 122(2) . . ?
C15 C14 H14 118(2) . . ?
C14 C15 C16 118.7(3) . . ?
C14 C15 H15 120(2) . . ?
C16 C15 H15 122(2) . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 H16 118.2(19) . . ?
C15 C16 H16 122.8(19) . . ?
N1 C17 C16 122.2(3) . . ?
N1 C17 H17 119(2) . . ?
C16 C17 H17 119(2) . . ?
N4 C18 C31 120.9(3) . . ?
N4 C18 C19 114.5(3) . . ?
C31 C18 C19 124.6(3) . . ?
N5 C19 C25 125.1(3) . . ?
N5 C19 C18 111.7(3) . . ?
C25 C19 C18 123.1(3) . . ?
O4 C20 N6 124.5(3) . . ?
O4 C20 C21 117.9(3) . . ?
N6 C20 C21 117.6(3) . . ?
C22 C21 C20 127.5(3) . . ?
C22 C21 S2 111.1(3) . . ?
C20 C21 S2 121.2(2) . . ?
C21 C22 C23 112.7(3) . . ?
C21 C22 H22 123(2) . . ?
C23 C22 H22 124(2) . . ?
C24 C23 C22 112.6(3) . . ?
C24 C23 H23 119(2) . . ?
C22 C23 H23 128(2) . . ?
C23 C24 S2 112.1(3) . . ?
C23 C24 H24 126(2) . . ?
S2 C24 H24 122(2) . . ?
C30 C25 C26 119.5(3) . . ?
C30 C25 C19 120.8(3) . . ?
C26 C25 C19 119.7(3) . . ?
C27 C26 C25 119.5(4) . . ?
C27 C26 H26 120(2) . . ?
C25 C26 H26 121(2) . . ?
C28 C27 C26 120.5(4) . . ?
C28 C27 H27 121(2) . . ?
C26 C27 H27 118(2) . . ?
C27 C28 C29 120.2(4) . . ?
C27 C28 H28 119(2) . . ?
C29 C28 H28 121(2) . . ?
C30 C29 C28 120.0(4) . . ?
C30 C29 H29 123(2) . . ?
C28 C29 H29 117(2) . . ?
C29 C30 C25 120.3(4) . . ?
C29 C30 H30 118(3) . . ?
C25 C30 H30 122(3) . . ?
C32 C31 C18 119.8(3) . . ?
C32 C31 H31 121(2) . . ?
C18 C31 H31 119(2) . . ?
C33 C32 C31 118.9(3) . . ?
C33 C32 H32 123.3(18) . . ?
C31 C32 H32 117.7(18) . . ?
C32 C33 C34 119.4(3) . . ?
C32 C33 H33 125(2) . . ?
C34 C33 H33 116(2) . . ?
N4 C34 C33 121.8(3) . . ?
N4 C34 H34 115.6(17) . . ?
C33 C34 H34 122.6(17) . . ?

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
O3 V1 O1 C3 -96.2(2) . . . . ?
O2 V1 O1 C3 153.3(2) . . . . ?
N1 V1 O1 C3 18.5(3) . . . . ?
N2 V1 O1 C3 3.6(2) . . . . ?
O2 V1 O1 C3 78.6(2) 2_667 . . . ?
O3 V1 N1 C17 -80.3(3) . . . . ?
O2 V1 N1 C17 28.1(3) . . . . ?
O1 V1 N1 C17 164.3(2) . . . . ?
N2 V1 N1 C17 179.3(3) . . . . ?
O2 V1 N1 C17 104.1(3) 2_667 . . . ?
O3 V1 N1 C1 100.4(2) . . . . ?
O2 V1 N1 C1 -151.2(2) . . . . ?
O1 V1 N1 C1 -15.0(3) . . . . ?
N2 V1 N1 C1 0.0(2) . . . . ?
O2 V1 N1 C1 -75.2(2) 2_667 . . . ?
C17 N1 C1 C14 -2.0(5) . . . . ?
V1 N1 C1 C14 177.4(2) . . . . ?
C17 N1 C1 C2 -179.1(3) . . . . ?
V1 N1 C1 C2 0.3(4) . . . . ?
O3 V1 O2 V1 178.04(10) . . . 2_667 ?
O1 V1 O2 V1 -77.77(11) . . . 2_667 ?
N1 V1 O2 V1 79.26(11) . . . 2_667 ?
N2 V1 O2 V1 8.5(3) . . . 2_667 ?
O2 V1 O2 V1 0.0 2_667 . . 2_667 ?
O3 V1 N2 C2 -92.9(3) . . . . ?
O2 V1 N2 C2 76.9(3) . . . . ?
O1 V1 N2 C2 171.3(3) . . . . ?
N1 V1 N2 C2 -0.3(2) . . . . ?
O2 V1 N2 C2 85.6(3) 2_667 . . . ?
O3 V1 N2 N3 90.2(2) . . . . ?
O2 V1 N2 N3 -100.0(3) . . . . ?
O1 V1 N2 N3 -5.5(2) . . . . ?
N1 V1 N2 N3 -177.1(2) . . . . ?
O2 V1 N2 N3 -91.3(2) 2_667 . . . ?
N3 N2 C2 C1 177.2(3) . . . . ?
V1 N2 C2 C1 0.5(4) . . . . ?
N3 N2 C2 C8 -0.5(5) . . . . ?
V1 N2 C2 C8 -177.2(2) . . . . ?
N1 C1 C2 N2 -0.5(4) . . . . ?
C14 C1 C2 N2 -177.5(3) . . . . ?
N1 C1 C2 C8 177.3(3) . . . . ?
C14 C1 C2 C8 0.3(5) . . . . ?
C2 N2 N3 C3 -170.9(3) . . . . ?
V1 N2 N3 C3 6.0(3) . . . . ?
V1 O1 C3 N3 -1.6(4) . . . . ?
V1 O1 C3 C4 179.6(2) . . . . ?
N2 N3 C3 O1 -3.1(4) . . . . ?
N2 N3 C3 C4 175.8(3) . . . . ?
O5 V2 O4 C20 -101.8(2) . . . . ?
O6 V2 O4 C20 148.0(2) . . . . ?
N4 V2 O4 C20 11.4(3) . . . . ?
N5 V2 O4 C20 -3.1(2) . . . . ?
O6 V2 O4 C20 73.6(2) 2_676 . . . ?
O5 V2 N4 C34 -81.4(3) . . . . ?
O6 V2 N4 C34 26.4(3) . . . . ?
O4 V2 N4 C34 164.3(2) . . . . ?
N5 V2 N4 C34 179.0(3) . . . . ?
O6 V2 N4 C34 101.9(3) 2_676 . . . ?
O5 V2 N4 C18 95.3(2) . . . . ?
O6 V2 N4 C18 -157.0(2) . . . . ?
O4 V2 N4 C18 -19.0(3) . . . . ?
N5 V2 N4 C18 -4.4(2) . . . . ?
O6 V2 N4 C18 -81.5(2) 2_676 . . . ?
O1 C3 C4 C5 -8.4(5) . . . . ?
N3 C3 C4 C5 172.7(3) . . . . ?
O1 C3 C4 S1 170.6(2) . . . . ?
N3 C3 C4 S1 -8.3(4) . . . . ?
C7 S1 C4 C5 1.1(3) . . . . ?
C7 S1 C4 C3 -178.1(3) . . . . ?
O5 V2 N5 C19 -88.5(3) . . . . ?
O6 V2 N5 C19 81.3(4) . . . . ?
O4 V2 N5 C19 175.2(3) . . . . ?
N4 V2 N5 C19 3.6(3) . . . . ?
O6 V2 N5 C19 89.0(3) 2_676 . . . ?
O5 V2 N5 N6 97.1(2) . . . . ?
O6 V2 N5 N6 -93.1(3) . . . . ?
O4 V2 N5 N6 0.8(2) . . . . ?
N4 V2 N5 N6 -170.8(2) . . . . ?
O6 V2 N5 N6 -85.4(2) 2_676 . . . ?
C3 C4 C5 C6 178.4(3) . . . . ?
S1 C4 C5 C6 -0.7(4) . . . . ?
O5 V2 O6 V2 177.22(10) . . . 2_676 ?
O4 V2 O6 V2 -78.15(11) . . . 2_676 ?
N4 V2 O6 V2 78.99(11) . . . 2_676 ?
N5 V2 O6 V2 7.7(3) . . . 2_676 ?
O6 V2 O6 V2 0.0 2_676 . . 2_676 ?
C19 N5 N6 C20 -172.9(3) . . . . ?
V2 N5 N6 C20 1.5(3) . . . . ?
C4 C5 C6 C7 -0.2(5) . . . . ?
C5 C6 C7 S1 1.1(4) . . . . ?
C4 S1 C7 C6 -1.2(3) . . . . ?
N2 C2 C8 C13 -130.7(4) . . . . ?
C1 C2 C8 C13 51.8(4) . . . . ?
N2 C2 C8 C9 47.8(5) . . . . ?
C1 C2 C8 C9 -129.6(3) . . . . ?
C13 C8 C9 C10 -1.4(5) . . . . ?
C2 C8 C9 C10 -179.9(3) . . . . ?
C8 C9 C10 C11 2.0(5) . . . . ?
C9 C10 C11 C12 -1.3(6) . . . . ?
C10 C11 C12 C13 0.0(5) . . . . ?
C11 C12 C13 C8 0.7(5) . . . . ?
C9 C8 C13 C12 0.0(5) . . . . ?
C2 C8 C13 C12 178.6(3) . . . . ?
N1 C1 C14 C15 2.8(5) . . . . ?
C2 C1 C14 C15 179.6(3) . . . . ?
C1 C14 C15 C16 -1.5(5) . . . . ?
C14 C15 C16 C17 -0.4(5) . . . . ?
C1 N1 C17 C16 0.0(5) . . . . ?
V1 N1 C17 C16 -179.3(3) . . . . ?
C15 C16 C17 N1 1.2(5) . . . . ?
C34 N4 C18 C31 2.1(5) . . . . ?
V2 N4 C18 C31 -174.7(2) . . . . ?
C34 N4 C18 C19 -178.4(3) . . . . ?
V2 N4 C18 C19 4.8(4) . . . . ?
N6 N5 C19 C25 -5.3(5) . . . . ?
V2 N5 C19 C25 -179.5(2) . . . . ?
N6 N5 C19 C18 172.0(3) . . . . ?
V2 N5 C19 C18 -2.2(4) . . . . ?
N4 C18 C19 N5 -1.7(4) . . . . ?
C31 C18 C19 N5 177.8(3) . . . . ?
N4 C18 C19 C25 175.7(3) . . . . ?
C31 C18 C19 C25 -4.8(5) . . . . ?
V2 O4 C20 N6 5.8(4) . . . . ?
V2 O4 C20 C21 -171.8(2) . . . . ?
N5 N6 C20 O4 -4.6(4) . . . . ?
N5 N6 C20 C21 172.9(3) . . . . ?
O4 C20 C21 C22 -12.0(5) . . . . ?
N6 C20 C21 C22 170.3(3) . . . . ?
O4 C20 C21 S2 162.4(2) . . . . ?
N6 C20 C21 S2 -15.3(5) . . . . ?
C24 S2 C21 C22 0.7(3) . . . . ?
C24 S2 C21 C20 -174.6(3) . . . . ?
C20 C21 C22 C23 174.5(3) . . . . ?
S2 C21 C22 C23 -0.3(4) . . . . ?
C21 C22 C23 C24 -0.3(5) . . . . ?
C22 C23 C24 S2 0.8(4) . . . . ?
C21 S2 C24 C23 -0.9(3) . . . . ?
N5 C19 C25 C30 127.6(4) . . . . ?
C18 C19 C25 C30 -49.4(5) . . . . ?
N5 C19 C25 C26 -51.6(5) . . . . ?
C18 C19 C25 C26 131.4(3) . . . . ?
C30 C25 C26 C27 2.6(5) . . . . ?
C19 C25 C26 C27 -178.2(3) . . . . ?
C25 C26 C27 C28 -2.2(5) . . . . ?
C26 C27 C28 C29 0.3(6) . . . . ?
C27 C28 C29 C30 1.3(6) . . . . ?
C28 C29 C30 C25 -0.9(5) . . . . ?
C26 C25 C30 C29 -1.1(5) . . . . ?
C19 C25 C30 C29 179.8(3) . . . . ?
N4 C18 C31 C32 -3.8(5) . . . . ?
C19 C18 C31 C32 176.8(3) . . . . ?
C18 C31 C32 C33 2.4(5) . . . . ?
C31 C32 C33 C34 0.5(5) . . . . ?
C18 N4 C34 C33 0.9(5) . . . . ?
V2 N4 C34 C33 177.6(3) . . . . ?
C32 C33 C34 N4 -2.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.142
_database_code_depnum_ccdc_archive 'CCDC 1018367'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_manar180

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 N4 O3 V'
_chemical_formula_sum            'C18 H13 N4 O3 V'
_chemical_formula_weight         384.26

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'
V V 0.3005 0.5294 '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
_symmetry_space_group_name_Hall  -P2ybc

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                   14.6312(5)
_cell_length_b                   8.2122(3)
_cell_length_c                   14.4503(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.765(2)
_cell_angle_gamma                90.00
_cell_volume                     1623.48(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    63735
_cell_measurement_theta_min      5.691
_cell_measurement_theta_max      42.873

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8567
_exptl_absorpt_correction_T_max  0.9507
_exptl_absorpt_process_details   'North et al., 1968'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            60921
_diffrn_reflns_av_R_equivalents  0.0951
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         27.58
_reflns_number_total             3733
_reflns_number_gt                2965
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
' SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite.'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS Version 2008/1 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122) '
_computing_structure_refinement  
'XL Version 2008/4 (George M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1294P)²+0.9086P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3733
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.2035
_refine_ls_wR_factor_gt          0.1837
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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
V1 V 0.42602(4) 0.06263(6) 0.39879(4) 0.0196(2) Uani 1 1 d . . .
O1 O 0.39152(15) 0.2530(2) 0.46281(16) 0.0221(5) Uani 1 1 d . . .
O2 O 0.54727(15) 0.0526(2) 0.44569(16) 0.0226(5) Uani 1 1 d . . .
O3 O 0.39668(16) 0.1342(3) 0.28791(16) 0.0254(5) Uani 1 1 d . . .
N1 N 0.39250(18) -0.1799(3) 0.34956(19) 0.0208(5) Uani 1 1 d . . .
N2 N 0.28328(18) 0.0132(3) 0.39894(18) 0.0202(5) Uani 1 1 d . . .
N3 N 0.23985(19) 0.1357(3) 0.4338(2) 0.0222(6) Uani 1 1 d . . .
N4 N 0.2179(2) 0.6579(3) 0.6037(2) 0.0309(7) Uani 1 1 d . . .
C1 C 0.3004(2) -0.2354(3) 0.3353(2) 0.0206(6) Uani 1 1 d . . .
C2 C 0.2371(2) -0.1185(4) 0.3610(2) 0.0202(6) Uani 1 1 d . . .
C3 C 0.3045(2) 0.2528(3) 0.4667(2) 0.0200(6) Uani 1 1 d . . .
C4 C 0.2752(2) 0.3938(4) 0.5147(2) 0.0217(6) Uani 1 1 d . . .
C5 C 0.3327(2) 0.5327(4) 0.5409(2) 0.0238(7) Uani 1 1 d . . .
H5 H 0.3913 0.5404 0.5296 0.029 Uiso 1 1 calc R . .
C6 C 0.3000(2) 0.6602(4) 0.5847(2) 0.0268(7) Uani 1 1 d . . .
H6 H 0.3385 0.7533 0.6018 0.032 Uiso 1 1 calc R . .
C7 C 0.1633(3) 0.5235(4) 0.5772(3) 0.0356(8) Uani 1 1 d . . .
H7 H 0.1050 0.5196 0.5894 0.043 Uiso 1 1 calc R . .
C8 C 0.1880(3) 0.3899(4) 0.5327(3) 0.0300(8) Uani 1 1 d . . .
H8 H 0.1472 0.2995 0.5152 0.036 Uiso 1 1 calc R . .
C9 C 0.1326(2) -0.1524(4) 0.3439(2) 0.0227(7) Uani 1 1 d . . .
C10 C 0.0725(2) -0.2122(4) 0.2520(2) 0.0257(7) Uani 1 1 d . . .
H10 H 0.0985 -0.2337 0.2032 0.031 Uiso 1 1 calc R . .
C11 C -0.0261(2) -0.2396(4) 0.2334(3) 0.0313(8) Uani 1 1 d . . .
H11 H -0.0662 -0.2795 0.1722 0.038 Uiso 1 1 calc R . .
C12 C -0.0644(2) -0.2074(4) 0.3060(3) 0.0340(8) Uani 1 1 d . . .
H12 H -0.1305 -0.2255 0.2936 0.041 Uiso 1 1 calc R . .
C13 C -0.0047(3) -0.1479(4) 0.3978(3) 0.0342(8) Uani 1 1 d . . .
H13 H -0.0309 -0.1265 0.4465 0.041 Uiso 1 1 calc R . .
C14 C 0.0929(2) -0.1207(4) 0.4167(2) 0.0255(7) Uani 1 1 d . . .
H14 H 0.1325 -0.0811 0.4781 0.031 Uiso 1 1 calc R . .
C15 C 0.2736(2) -0.3930(4) 0.3027(2) 0.0228(7) Uani 1 1 d . . .
H15 H 0.2117 -0.4314 0.2956 0.027 Uiso 1 1 calc R . .
C16 C 0.3388(2) -0.4925(4) 0.2808(2) 0.0267(7) Uani 1 1 d . . .
H16 H 0.3210 -0.5978 0.2578 0.032 Uiso 1 1 calc R . .
C17 C 0.4311(2) -0.4341(3) 0.2933(2) 0.0244(7) Uani 1 1 d . . .
H17 H 0.4761 -0.4991 0.2786 0.029 Uiso 1 1 calc R . .
C18 C 0.4551(2) -0.2770(4) 0.3283(2) 0.0229(7) Uani 1 1 d . . .
H18 H 0.5173 -0.2380 0.3373 0.028 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O3 1.615(2) . ?
V1 O2 1.662(2) . ?
V1 O1 1.972(2) . ?
V1 N1 2.113(3) . ?
V1 N2 2.128(3) . ?
V1 O2 2.340(2) 3_656 ?
O1 C3 1.294(4) . ?
O2 V1 2.340(2) 3_656 ?
N1 C18 1.330(4) . ?
N1 C1 1.367(4) . ?
N2 C2 1.290(4) . ?
N2 N3 1.377(3) . ?
N3 C3 1.314(4) . ?
N4 C6 1.325(4) . ?
N4 C7 1.336(5) . ?
C1 C15 1.386(4) . ?
C1 C2 1.471(4) . ?
C2 C9 1.485(4) . ?
C3 C4 1.489(4) . ?
C4 C5 1.389(4) . ?
C4 C8 1.389(4) . ?
C5 C6 1.393(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.383(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C14 1.395(4) . ?
C9 C10 1.396(4) . ?
C10 C11 1.389(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.393(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.375(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 V1 O2 107.01(11) . . ?
O3 V1 O1 98.89(10) . . ?
O2 V1 O1 105.19(10) . . ?
O3 V1 N1 93.48(10) . . ?
O2 V1 N1 100.21(10) . . ?
O1 V1 N1 146.93(9) . . ?
O3 V1 N2 98.89(11) . . ?
O2 V1 N2 153.68(11) . . ?
O1 V1 N2 74.70(9) . . ?
N1 V1 N2 73.14(9) . . ?
O3 V1 O2 174.22(10) . 3_656 ?
O2 V1 O2 78.32(10) . 3_656 ?
O1 V1 O2 81.57(8) . 3_656 ?
N1 V1 O2 83.23(9) . 3_656 ?
N2 V1 O2 75.63(8) . 3_656 ?
C3 O1 V1 116.03(18) . . ?
V1 O2 V1 101.68(10) . 3_656 ?
C18 N1 C1 119.2(3) . . ?
C18 N1 V1 123.1(2) . . ?
C1 N1 V1 117.65(19) . . ?
C2 N2 N3 121.8(3) . . ?
C2 N2 V1 121.7(2) . . ?
N3 N2 V1 116.19(18) . . ?
C3 N3 N2 107.5(2) . . ?
C6 N4 C7 116.5(3) . . ?
N1 C1 C15 120.6(3) . . ?
N1 C1 C2 114.8(3) . . ?
C15 C1 C2 124.6(3) . . ?
N2 C2 C1 111.9(3) . . ?
N2 C2 C9 125.5(3) . . ?
C1 C2 C9 122.6(3) . . ?
O1 C3 N3 125.3(3) . . ?
O1 C3 C4 118.0(3) . . ?
N3 C3 C4 116.6(3) . . ?
C5 C4 C8 118.4(3) . . ?
C5 C4 C3 121.2(3) . . ?
C8 C4 C3 120.3(3) . . ?
C4 C5 C6 117.9(3) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
N4 C6 C5 124.5(3) . . ?
N4 C6 H6 117.7 . . ?
C5 C6 H6 117.7 . . ?
N4 C7 C8 124.1(3) . . ?
N4 C7 H7 118.0 . . ?
C8 C7 H7 118.0 . . ?
C7 C8 C4 118.5(3) . . ?
C7 C8 H8 120.7 . . ?
C4 C8 H8 120.7 . . ?
C14 C9 C10 119.4(3) . . ?
C14 C9 C2 121.2(3) . . ?
C10 C9 C2 119.3(3) . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 120.1(3) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
C16 C15 C1 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C1 C15 H15 120.1 . . ?
C15 C16 C17 119.3(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C18 118.7(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
N1 C18 C17 122.4(3) . . ?
N1 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 V1 O1 C3 93.6(2) . . . . ?
O2 V1 O1 C3 -155.9(2) . . . . ?
N1 V1 O1 C3 -17.0(3) . . . . ?
N2 V1 O1 C3 -3.2(2) . . . . ?
O2 V1 O1 C3 -80.5(2) 3_656 . . . ?
O3 V1 O2 V1 -177.69(10) . . . 3_656 ?
O1 V1 O2 V1 77.80(10) . . . 3_656 ?
N1 V1 O2 V1 -80.82(10) . . . 3_656 ?
N2 V1 O2 V1 -8.3(3) . . . 3_656 ?
O2 V1 O2 V1 0.0 3_656 . . 3_656 ?
O3 V1 N1 C18 84.4(3) . . . . ?
O2 V1 N1 C18 -23.6(3) . . . . ?
O1 V1 N1 C18 -163.4(2) . . . . ?
N2 V1 N1 C18 -177.3(3) . . . . ?
O2 V1 N1 C18 -100.3(2) 3_656 . . . ?
O3 V1 N1 C1 -92.8(2) . . . . ?
O2 V1 N1 C1 159.2(2) . . . . ?
O1 V1 N1 C1 19.4(3) . . . . ?
N2 V1 N1 C1 5.5(2) . . . . ?
O2 V1 N1 C1 82.4(2) 3_656 . . . ?
O3 V1 N2 C2 82.3(2) . . . . ?
O2 V1 N2 C2 -87.4(3) . . . . ?
O1 V1 N2 C2 179.2(3) . . . . ?
N1 V1 N2 C2 -8.6(2) . . . . ?
O2 V1 N2 C2 -95.8(2) 3_656 . . . ?
O3 V1 N2 N3 -92.2(2) . . . . ?
O2 V1 N2 N3 98.1(3) . . . . ?
O1 V1 N2 N3 4.69(19) . . . . ?
N1 V1 N2 N3 176.9(2) . . . . ?
O2 V1 N2 N3 89.7(2) 3_656 . . . ?
C2 N2 N3 C3 -179.5(3) . . . . ?
V1 N2 N3 C3 -5.0(3) . . . . ?
C18 N1 C1 C15 2.4(4) . . . . ?
V1 N1 C1 C15 179.7(2) . . . . ?
C18 N1 C1 C2 -180.0(3) . . . . ?
V1 N1 C1 C2 -2.6(3) . . . . ?
N3 N2 C2 C1 -176.2(2) . . . . ?
V1 N2 C2 C1 9.7(3) . . . . ?
N3 N2 C2 C9 4.0(5) . . . . ?
V1 N2 C2 C9 -170.2(2) . . . . ?
N1 C1 C2 N2 -4.3(4) . . . . ?
C15 C1 C2 N2 173.3(3) . . . . ?
N1 C1 C2 C9 175.5(3) . . . . ?
C15 C1 C2 C9 -6.9(5) . . . . ?
V1 O1 C3 N3 1.6(4) . . . . ?
V1 O1 C3 C4 179.8(2) . . . . ?
N2 N3 C3 O1 2.4(4) . . . . ?
N2 N3 C3 C4 -175.8(2) . . . . ?
O1 C3 C4 C5 9.8(4) . . . . ?
N3 C3 C4 C5 -171.9(3) . . . . ?
O1 C3 C4 C8 -171.4(3) . . . . ?
N3 C3 C4 C8 6.9(4) . . . . ?
C8 C4 C5 C6 0.6(5) . . . . ?
C3 C4 C5 C6 179.4(3) . . . . ?
C7 N4 C6 C5 -0.9(5) . . . . ?
C4 C5 C6 N4 0.4(5) . . . . ?
C6 N4 C7 C8 0.5(6) . . . . ?
N4 C7 C8 C4 0.5(6) . . . . ?
C5 C4 C8 C7 -1.0(5) . . . . ?
C3 C4 C8 C7 -179.8(3) . . . . ?
N2 C2 C9 C14 -46.1(5) . . . . ?
C1 C2 C9 C14 134.1(3) . . . . ?
N2 C2 C9 C10 131.8(3) . . . . ?
C1 C2 C9 C10 -48.0(4) . . . . ?
C14 C9 C10 C11 0.1(4) . . . . ?
C2 C9 C10 C11 -177.9(3) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C12 C13 C14 C9 0.1(5) . . . . ?
C10 C9 C14 C13 -0.2(5) . . . . ?
C2 C9 C14 C13 177.7(3) . . . . ?
N1 C1 C15 C16 -2.5(4) . . . . ?
C2 C1 C15 C16 -179.9(3) . . . . ?
C1 C15 C16 C17 1.1(5) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C1 N1 C18 C17 -0.9(5) . . . . ?
V1 N1 C18 C17 -178.0(2) . . . . ?
C16 C17 C18 N1 -0.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         2.055
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.167
_database_code_depnum_ccdc_archive 'CCDC 1018368'
