# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 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 
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#  data retrieval see:
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data_1
_database_code_depnum_ccdc_archive 'CCDC 933765'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 N4 O4'
_chemical_formula_weight         416.43
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a                   8.0290(3)
_cell_length_b                   18.9754(9)
_cell_length_c                   13.3607(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.218(4)
_cell_angle_gamma                90.00
_cell_volume                     1954.55(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    3935
_cell_measurement_theta_min      3.4422
_cell_measurement_theta_max      69.5828
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7576
_exptl_absorpt_correction_T_max  0.7859
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10835
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.16
_diffrn_reflns_theta_max         69.71
_reflns_number_total             3589
_reflns_number_gt                2761
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_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^)+(0.0896P)^2^+1.9323P] 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         3589
_refine_ls_number_parameters     291
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.2295
_refine_ls_wR_factor_gt          0.2162
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.142
_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
N4 N 0.1916(3) 0.04482(16) 0.0089(2) 0.0594(7) Uani 1 1 d . . .
H4 H 0.1087 0.0303 -0.0427 0.071 Uiso 1 1 calc R . .
N3 N 0.4412(3) 0.08742(15) 0.0997(2) 0.0564(7) Uani 1 1 d . . .
N2 N 0.5779(4) 0.06354(16) 0.3338(2) 0.0643(8) Uani 1 1 d . . .
C10 C 0.3442(4) 0.06927(19) 0.0013(3) 0.0576(8) Uani 1 1 d . . .
O1 O 0.0583(3) 0.02343(16) 0.14015(19) 0.0714(8) Uani 1 1 d D . .
C15 C 0.1632(5) 0.1475(2) 0.3189(3) 0.0679(10) Uani 1 1 d . . .
H15 H 0.1150 0.1516 0.2473 0.081 Uiso 1 1 calc R . .
C9 C 0.1861(4) 0.0462(2) 0.1120(3) 0.0575(8) Uani 1 1 d . . .
C7 C 0.4138(4) 0.08386(18) 0.2808(3) 0.0573(8) Uani 1 1 d . . .
C4 C 0.5892(5) 0.0746(2) 0.4349(3) 0.0656(10) Uani 1 1 d . . .
N1 N 0.4375(4) 0.10220(17) 0.4474(2) 0.0657(8) Uani 1 1 d . . .
C6 C 0.3230(5) 0.1104(2) 0.3477(3) 0.0617(9) Uani 1 1 d . . .
C5 C 0.7281(6) 0.0610(2) 0.5237(3) 0.0805(12) Uani 1 1 d . . .
H5 H 0.8323 0.0432 0.5169 0.097 Uiso 1 1 calc R . .
C11 C 0.4111(5) 0.0777(2) -0.0837(3) 0.0695(10) Uani 1 1 d . . .
H11 H 0.3457 0.0659 -0.1507 0.083 Uiso 1 1 calc R . .
C14 C 0.6039(5) 0.1146(2) 0.1166(3) 0.0692(10) Uani 1 1 d . . .
H14 H 0.6681 0.1274 0.1834 0.083 Uiso 1 1 calc R . .
C8 C 0.3445(4) 0.07469(19) 0.1696(3) 0.0568(8) Uani 1 1 d . . .
O2 O -0.1218(5) 0.2329(2) 0.2303(4) 0.1181(14) Uani 1 1 d . . .
C13 C 0.6710(5) 0.1226(3) 0.0348(4) 0.0815(12) Uani 1 1 d . . .
H13 H 0.7821 0.1409 0.0459 0.098 Uiso 1 1 calc R . .
C12 C 0.5759(6) 0.1038(3) -0.0656(4) 0.0811(12) Uani 1 1 d . . .
H12 H 0.6244 0.1091 -0.1207 0.097 Uiso 1 1 calc R . .
O3 O -0.1199(5) -0.0116(2) 0.3006(3) 0.1050(11) Uani 1 1 d D . .
C3 C 0.4188(7) 0.1156(3) 0.5445(3) 0.0875(13) Uani 1 1 d . . .
H3 H 0.3157 0.1340 0.5520 0.105 Uiso 1 1 calc R . .
C1 C 0.7077(7) 0.0741(3) 0.6192(4) 0.0945(15) Uani 1 1 d . . .
H1 H 0.7979 0.0649 0.6787 0.113 Uiso 1 1 calc R . .
C17 C -0.0862(6) 0.2183(3) 0.3236(5) 0.0909(14) Uani 1 1 d . . .
C18 C -0.2061(6) 0.2400(3) 0.3877(6) 0.1010(17) Uani 1 1 d U . .
C16 C 0.0703(5) 0.1773(3) 0.3746(4) 0.0791(12) Uani 1 1 d . . .
H16 H 0.1040 0.1725 0.4467 0.095 Uiso 1 1 calc R . .
C23 C -0.1597(8) 0.2372(3) 0.4944(6) 0.1098(18) Uani 1 1 d U . .
H23 H -0.0491 0.2217 0.5298 0.132 Uiso 1 1 calc R . .
C19 C -0.3689(8) 0.2638(4) 0.3373(7) 0.146(3) Uani 1 1 d U . .
H19 H -0.4052 0.2669 0.2650 0.175 Uiso 1 1 calc R . .
C2 C 0.5514(8) 0.1016(3) 0.6284(4) 0.1000(16) Uani 1 1 d . . .
H2 H 0.5389 0.1105 0.6944 0.120 Uiso 1 1 calc R . .
C22 C -0.2710(10) 0.2564(3) 0.5504(7) 0.134(2) Uani 1 1 d U . .
H22 H -0.2356 0.2543 0.6228 0.161 Uiso 1 1 calc R . .
C20 C -0.4833(9) 0.2840(4) 0.3990(9) 0.154(3) Uani 1 1 d U . .
H20 H -0.5940 0.3010 0.3670 0.184 Uiso 1 1 calc R . .
C21 C -0.4284(12) 0.2780(4) 0.5015(9) 0.160(3) Uani 1 1 d U . .
H21 H -0.5039 0.2895 0.5406 0.191 Uiso 1 1 calc R . .
O4 O -0.1427(16) -0.1560(10) 0.3556(10) 0.355(6) Uani 1 1 d GD . .
H4A H -0.2355 -0.1772 0.3233 0.532 Uiso 1 1 d GD . .
H4B H -0.1417 -0.1151 0.3298 0.532 Uiso 1 1 d GD . .
H3A H -0.196(6) 0.016(3) 0.312(5) 0.13(2) Uiso 1 1 d D . .
H3B H -0.051(10) 0.011(3) 0.274(8) 0.25(5) Uiso 1 1 d D . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N4 0.0483(15) 0.0709(19) 0.0541(16) -0.0031(14) 0.0065(12) -0.0057(13)
N3 0.0456(14) 0.0600(17) 0.0601(16) 0.0005(13) 0.0088(12) -0.0025(12)
N2 0.0528(16) 0.0666(18) 0.0652(19) -0.0025(14) 0.0026(14) 0.0002(14)
C10 0.0526(18) 0.059(2) 0.058(2) 0.0030(15) 0.0108(15) 0.0009(15)
O1 0.0514(14) 0.099(2) 0.0612(15) -0.0089(13) 0.0120(11) -0.0171(13)
C15 0.057(2) 0.072(2) 0.067(2) -0.0057(18) 0.0057(17) -0.0016(18)
C9 0.0483(18) 0.065(2) 0.0557(19) -0.0030(16) 0.0086(15) -0.0035(15)
C7 0.0483(18) 0.059(2) 0.0580(19) -0.0011(15) 0.0037(15) -0.0049(15)
C4 0.062(2) 0.064(2) 0.060(2) -0.0014(17) -0.0002(17) -0.0029(17)
N1 0.0626(18) 0.0702(19) 0.0556(17) -0.0015(14) 0.0022(14) -0.0018(15)
C6 0.0542(19) 0.070(2) 0.0552(19) -0.0027(16) 0.0053(15) -0.0024(16)
C5 0.070(3) 0.075(3) 0.078(3) 0.003(2) -0.009(2) -0.002(2)
C11 0.069(2) 0.074(2) 0.064(2) 0.0037(18) 0.0172(18) 0.0008(19)
C14 0.053(2) 0.075(2) 0.076(2) 0.0020(19) 0.0109(18) -0.0125(18)
C8 0.0476(17) 0.063(2) 0.0562(19) -0.0026(15) 0.0087(15) -0.0036(15)
O2 0.090(3) 0.119(3) 0.123(3) 0.003(2) -0.006(2) 0.017(2)
C13 0.060(2) 0.096(3) 0.089(3) 0.009(2) 0.022(2) -0.017(2)
C12 0.073(3) 0.095(3) 0.081(3) 0.013(2) 0.030(2) -0.004(2)
O3 0.088(2) 0.113(3) 0.115(3) 0.009(2) 0.032(2) 0.021(2)
C3 0.091(3) 0.111(4) 0.057(2) -0.003(2) 0.013(2) 0.001(3)
C1 0.099(4) 0.100(4) 0.063(3) 0.005(2) -0.014(2) -0.006(3)
C17 0.064(3) 0.076(3) 0.119(4) -0.018(3) 0.003(3) -0.005(2)
C18 0.061(3) 0.066(3) 0.169(5) -0.031(3) 0.020(3) -0.001(2)
C16 0.061(2) 0.093(3) 0.080(3) -0.013(2) 0.013(2) 0.007(2)
C23 0.101(4) 0.079(3) 0.167(5) -0.012(3) 0.066(4) -0.003(3)
C19 0.087(4) 0.127(5) 0.204(6) -0.061(5) 0.009(4) 0.016(3)
C2 0.109(4) 0.121(4) 0.057(3) -0.001(2) 0.003(2) -0.003(3)
C22 0.122(5) 0.094(4) 0.215(7) -0.022(4) 0.093(5) 0.008(3)
C20 0.077(4) 0.147(6) 0.229(7) -0.056(6) 0.030(5) 0.023(4)
C21 0.129(6) 0.127(5) 0.237(8) -0.046(6) 0.075(6) -0.002(5)
O4 0.350(17) 0.42(2) 0.280(11) 0.005(12) 0.071(10) -0.017(13)
_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
N4 C10 1.340(4) . ?
N4 C9 1.390(4) . ?
N4 H4 0.8600 . ?
N3 C14 1.363(4) . ?
N3 C10 1.372(4) . ?
N3 C8 1.392(4) . ?
N2 C4 1.345(5) . ?
N2 C7 1.366(4) . ?
C10 C11 1.394(5) . ?
O1 C9 1.264(4) . ?
C15 C16 1.319(5) . ?
C15 C6 1.419(5) . ?
C15 H15 0.9300 . ?
C9 C8 1.399(5) . ?
C7 C6 1.396(5) . ?
C7 C8 1.444(5) . ?
C4 N1 1.378(5) . ?
C4 C5 1.407(5) . ?
N1 C3 1.370(5) . ?
N1 C6 1.399(4) . ?
C5 C1 1.355(7) . ?
C5 H5 0.9300 . ?
C11 C12 1.370(6) . ?
C11 H11 0.9300 . ?
C14 C13 1.355(6) . ?
C14 H14 0.9300 . ?
O2 C17 1.230(6) . ?
C13 C12 1.392(6) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
O3 H3A 0.849(11) . ?
O3 H3B 0.851(11) . ?
C3 C2 1.339(7) . ?
C3 H3 0.9300 . ?
C1 C2 1.396(8) . ?
C1 H1 0.9300 . ?
C17 C16 1.473(6) . ?
C17 C18 1.513(8) . ?
C18 C19 1.369(8) . ?
C18 C23 1.371(8) . ?
C16 H16 0.9300 . ?
C23 C22 1.365(8) . ?
C23 H23 0.9300 . ?
C19 C20 1.447(10) . ?
C19 H19 0.9300 . ?
C2 H2 0.9300 . ?
C22 C21 1.315(11) . ?
C22 H22 0.9300 . ?
C20 C21 1.320(11) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
O4 H4A 0.8500 . ?
O4 H4B 0.8501 . ?
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
C10 N4 C9 110.6(3) . . ?
C10 N4 H4 124.7 . . ?
C9 N4 H4 124.7 . . ?
C14 N3 C10 121.0(3) . . ?
C14 N3 C8 130.0(3) . . ?
C10 N3 C8 109.0(3) . . ?
C4 N2 C7 105.1(3) . . ?
N4 C10 N3 107.4(3) . . ?
N4 C10 C11 132.1(3) . . ?
N3 C10 C11 120.5(3) . . ?
C16 C15 C6 132.1(4) . . ?
C16 C15 H15 113.9 . . ?
C6 C15 H15 113.9 . . ?
O1 C9 N4 122.8(3) . . ?
O1 C9 C8 131.1(3) . . ?
N4 C9 C8 106.1(3) . . ?
N2 C7 C6 111.7(3) . . ?
N2 C7 C8 122.6(3) . . ?
C6 C7 C8 125.6(3) . . ?
N2 C4 N1 111.5(3) . . ?
N2 C4 C5 129.3(4) . . ?
N1 C4 C5 119.2(4) . . ?
C3 N1 C4 121.3(3) . . ?
C3 N1 C6 131.6(4) . . ?
C4 N1 C6 107.1(3) . . ?
C7 C6 N1 104.4(3) . . ?
C7 C6 C15 126.8(3) . . ?
N1 C6 C15 128.1(3) . . ?
C1 C5 C4 119.0(5) . . ?
C1 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C12 C11 C10 118.1(4) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C13 C14 N3 119.2(4) . . ?
C13 C14 H14 120.4 . . ?
N3 C14 H14 120.4 . . ?
N3 C8 C9 106.8(3) . . ?
N3 C8 C7 122.9(3) . . ?
C9 C8 C7 130.0(3) . . ?
C14 C13 C12 120.9(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C11 C12 C13 120.4(4) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
H3A O3 H3B 110(3) . . ?
C2 C3 N1 119.0(5) . . ?
C2 C3 H3 120.5 . . ?
N1 C3 H3 120.5 . . ?
C5 C1 C2 120.0(4) . . ?
C5 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
O2 C17 C16 120.9(5) . . ?
O2 C17 C18 120.5(5) . . ?
C16 C17 C18 118.5(5) . . ?
C19 C18 C23 118.0(6) . . ?
C19 C18 C17 118.9(7) . . ?
C23 C18 C17 123.2(5) . . ?
C15 C16 C17 120.7(5) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C22 C23 C18 122.0(7) . . ?
C22 C23 H23 119.0 . . ?
C18 C23 H23 119.0 . . ?
C18 C19 C20 118.6(8) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C3 C2 C1 121.6(5) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C21 C22 C23 119.8(9) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C21 C20 C19 119.1(8) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C22 C21 C20 122.5(9) . . ?
C22 C21 H21 118.7 . . ?
C20 C21 H21 118.7 . . ?
H4A O4 H4B 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N4 C10 N3 -0.2(4) . . . . ?
C9 N4 C10 C11 179.5(4) . . . . ?
C14 N3 C10 N4 -179.6(3) . . . . ?
C8 N3 C10 N4 -0.9(4) . . . . ?
C14 N3 C10 C11 0.6(5) . . . . ?
C8 N3 C10 C11 179.3(3) . . . . ?
C10 N4 C9 O1 -177.3(3) . . . . ?
C10 N4 C9 C8 1.2(4) . . . . ?
C4 N2 C7 C6 2.3(4) . . . . ?
C4 N2 C7 C8 -174.7(3) . . . . ?
C7 N2 C4 N1 -0.7(4) . . . . ?
C7 N2 C4 C5 178.1(4) . . . . ?
N2 C4 N1 C3 178.0(4) . . . . ?
C5 C4 N1 C3 -0.9(6) . . . . ?
N2 C4 N1 C6 -1.0(4) . . . . ?
C5 C4 N1 C6 -180.0(4) . . . . ?
N2 C7 C6 N1 -2.9(4) . . . . ?
C8 C7 C6 N1 174.0(3) . . . . ?
N2 C7 C6 C15 167.8(4) . . . . ?
C8 C7 C6 C15 -15.3(6) . . . . ?
C3 N1 C6 C7 -176.6(4) . . . . ?
C4 N1 C6 C7 2.3(4) . . . . ?
C3 N1 C6 C15 12.9(7) . . . . ?
C4 N1 C6 C15 -168.2(4) . . . . ?
C16 C15 C6 C7 -176.6(4) . . . . ?
C16 C15 C6 N1 -8.0(7) . . . . ?
N2 C4 C5 C1 -177.5(4) . . . . ?
N1 C4 C5 C1 1.2(6) . . . . ?
N4 C10 C11 C12 -179.2(4) . . . . ?
N3 C10 C11 C12 0.6(6) . . . . ?
C10 N3 C14 C13 -1.0(6) . . . . ?
C8 N3 C14 C13 -179.5(4) . . . . ?
C14 N3 C8 C9 -179.8(4) . . . . ?
C10 N3 C8 C9 1.6(4) . . . . ?
C14 N3 C8 C7 -5.6(6) . . . . ?
C10 N3 C8 C7 175.7(3) . . . . ?
O1 C9 C8 N3 176.7(4) . . . . ?
N4 C9 C8 N3 -1.7(4) . . . . ?
O1 C9 C8 C7 3.1(7) . . . . ?
N4 C9 C8 C7 -175.3(4) . . . . ?
N2 C7 C8 N3 -41.2(5) . . . . ?
C6 C7 C8 N3 142.3(4) . . . . ?
N2 C7 C8 C9 131.5(4) . . . . ?
C6 C7 C8 C9 -45.0(6) . . . . ?
N3 C14 C13 C12 0.3(7) . . . . ?
C10 C11 C12 C13 -1.3(7) . . . . ?
C14 C13 C12 C11 0.9(7) . . . . ?
C4 N1 C3 C2 0.2(7) . . . . ?
C6 N1 C3 C2 179.0(5) . . . . ?
C4 C5 C1 C2 -0.7(7) . . . . ?
O2 C17 C18 C19 12.3(8) . . . . ?
C16 C17 C18 C19 -165.6(5) . . . . ?
O2 C17 C18 C23 -167.5(5) . . . . ?
C16 C17 C18 C23 14.6(7) . . . . ?
C6 C15 C16 C17 174.7(4) . . . . ?
O2 C17 C16 C15 -9.0(7) . . . . ?
C18 C17 C16 C15 168.8(4) . . . . ?
C19 C18 C23 C22 0.8(9) . . . . ?
C17 C18 C23 C22 -179.4(5) . . . . ?
C23 C18 C19 C20 -0.6(9) . . . . ?
C17 C18 C19 C20 179.6(6) . . . . ?
N1 C3 C2 C1 0.2(8) . . . . ?
C5 C1 C2 C3 0.0(9) . . . . ?
C18 C23 C22 C21 0.5(10) . . . . ?
C18 C19 C20 C21 -0.9(12) . . . . ?
C23 C22 C21 C20 -2.1(13) . . . . ?
C19 C20 C21 C22 2.3(14) . . . . ?
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
N4 H4 O1 0.86 1.89 2.728(4) 165.8 3
O4 H4A O2 0.85 2.07 2.850(17) 152.6 2_445
O4 H4B O3 0.85 2.02 2.857(18) 167.9 .
O3 H3A N2 0.849(11) 2.121(18) 2.953(5) 166(6) 1_455
O3 H3B O1 0.851(11) 2.21(6) 2.966(5) 147(10) .
_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        69.71
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.064



data_2
_database_code_depnum_ccdc_archive 'CCDC 931977'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 N5 O4'
_chemical_formula_weight         417.42
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
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                   32.6356(16)
_cell_length_b                   8.5232(3)
_cell_length_c                   15.4600(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.224(5)
_cell_angle_gamma                90.00
_cell_volume                     3857.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    8231
_cell_measurement_theta_min      3.0164
_cell_measurement_theta_max      62.6767
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744
_exptl_absorpt_coefficient_mu    0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7397
_exptl_absorpt_correction_T_max  0.7858
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18919
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         62.76
_reflns_number_total             3085
_reflns_number_gt                2703
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_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^)+(0.0555P)^2^+1.6128P] 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         3085
_refine_ls_number_parameters     296
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.051
_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
O2 O 0.06081(4) 0.32258(12) 0.43649(9) 0.0521(3) Uani 1 1 d . . .
N1 N 0.13134(4) -0.07856(14) 0.34436(9) 0.0363(3) Uani 1 1 d . . .
C3 C 0.12741(6) -0.3523(2) 0.24746(12) 0.0505(4) Uani 1 1 d . . .
H3 H 0.1267 -0.4445 0.2147 0.061 Uiso 1 1 calc R . .
N5 N 0.04005(4) 0.20901(14) 0.54889(9) 0.0417(3) Uani 1 1 d . . .
H5 H 0.0256 0.2880 0.5567 0.050 Uiso 1 1 calc R . .
N4 N 0.06961(4) -0.02549(14) 0.56253(9) 0.0366(3) Uani 1 1 d . . .
N2 N 0.08569(4) -0.16980(14) 0.40740(9) 0.0399(3) Uani 1 1 d . . .
O1 O 0.20270(5) 0.46501(17) 0.50543(10) 0.0710(4) Uani 1 1 d . . .
C12 C 0.29177(6) 0.6427(2) 0.40199(15) 0.0561(5) Uani 1 1 d . . .
H12 H 0.3142 0.7152 0.4379 0.067 Uiso 1 1 calc R . .
C1 C 0.10634(5) -0.20461(17) 0.35184(11) 0.0387(4) Uani 1 1 d . . .
N3 N 0.28732(6) 0.60533(18) 0.31471(13) 0.0614(4) Uani 1 1 d . . .
C2 C 0.10488(6) -0.34424(19) 0.30282(12) 0.0469(4) Uani 1 1 d . . .
H2 H 0.0886 -0.4303 0.3082 0.056 Uiso 1 1 calc R . .
C11 C 0.26525(6) 0.58089(19) 0.44263(13) 0.0482(4) Uani 1 1 d . . .
H11 H 0.2695 0.6131 0.5035 0.058 Uiso 1 1 calc R . .
C15 C 0.09799(5) -0.01965(17) 0.43754(10) 0.0355(3) Uani 1 1 d . . .
C22 C 0.08168(5) -0.17375(18) 0.59925(11) 0.0435(4) Uani 1 1 d . . .
H22 H 0.0990 -0.2377 0.5792 0.052 Uiso 1 1 calc R . .
C16 C 0.08038(5) 0.05782(17) 0.49682(11) 0.0371(3) Uani 1 1 d . . .
C10 C 0.23229(5) 0.47047(17) 0.39189(12) 0.0415(4) Uani 1 1 d . . .
C7 C 0.15101(5) 0.18718(17) 0.42584(11) 0.0395(4) Uani 1 1 d . . .
H7 H 0.1460 0.2461 0.4709 0.047 Uiso 1 1 calc R . .
C4 C 0.15173(6) -0.2222(2) 0.23947(12) 0.0490(4) Uani 1 1 d . . .
H4 H 0.1670 -0.2289 0.2010 0.059 Uiso 1 1 calc R . .
C21 C 0.06802(6) -0.2257(2) 0.66523(12) 0.0501(4) Uani 1 1 d . . .
H21 H 0.0759 -0.3267 0.6899 0.060 Uiso 1 1 calc R . .
C14 C 0.22664(6) 0.4332(2) 0.30012(13) 0.0511(4) Uani 1 1 d . . .
H14 H 0.2045 0.3613 0.2626 0.061 Uiso 1 1 calc R . .
C18 C 0.04511(5) 0.06986(18) 0.59397(11) 0.0391(4) Uani 1 1 d . . .
C17 C 0.06126(5) 0.20796(17) 0.48777(11) 0.0400(4) Uani 1 1 d . . .
C19 C 0.03095(5) 0.0176(2) 0.66140(11) 0.0459(4) Uani 1 1 d . . .
H19 H 0.0140 0.0822 0.6820 0.055 Uiso 1 1 calc R . .
C9 C 0.20384(6) 0.39926(19) 0.43605(12) 0.0443(4) Uani 1 1 d . . .
C8 C 0.17959(6) 0.25399(19) 0.39533(12) 0.0449(4) Uani 1 1 d . . .
H8 H 0.1840 0.2054 0.3463 0.054 Uiso 1 1 calc R . .
C6 C 0.12711(5) 0.04250(17) 0.40132(10) 0.0358(3) Uani 1 1 d . . .
C20 C 0.04251(6) -0.1314(2) 0.69689(12) 0.0510(4) Uani 1 1 d . . .
H20 H 0.0334 -0.1695 0.7420 0.061 Uiso 1 1 calc R . .
C5 C 0.15344(6) -0.08693(19) 0.28673(11) 0.0434(4) Uani 1 1 d . . .
H5A H 0.1694 -0.0008 0.2803 0.052 Uiso 1 1 calc R . .
C13 C 0.25414(7) 0.5035(2) 0.26484(15) 0.0601(5) Uani 1 1 d . . .
H13 H 0.2493 0.4785 0.2025 0.072 Uiso 1 1 calc R . .
O4 O 0.13383(6) 0.47802(17) 0.06562(11) 0.0682(4) Uani 1 1 d D . .
O3 O 0.01429(5) 0.60537(16) 0.39902(12) 0.0677(4) Uani 1 1 d D . .
H3A H 0.0250(8) 0.508(2) 0.4093(17) 0.089(8) Uiso 1 1 d D . .
H4A H 0.1559(8) 0.494(3) 0.047(2) 0.111(10) Uiso 1 1 d D . .
H3B H 0.0363(8) 0.667(3) 0.400(2) 0.121(11) Uiso 1 1 d D . .
H4B H 0.1092(9) 0.532(4) 0.023(2) 0.149(13) Uiso 1 1 d D . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0580(7) 0.0374(6) 0.0716(8) 0.0073(5) 0.0385(6) 0.0054(5)
N1 0.0367(7) 0.0375(7) 0.0398(7) 0.0007(5) 0.0215(6) 0.0026(5)
C3 0.0576(11) 0.0445(9) 0.0539(10) -0.0098(7) 0.0287(9) 0.0039(8)
N5 0.0407(7) 0.0379(7) 0.0524(8) -0.0055(6) 0.0260(6) 0.0041(5)
N4 0.0350(7) 0.0389(7) 0.0405(7) -0.0034(5) 0.0207(6) -0.0007(5)
N2 0.0453(7) 0.0342(7) 0.0481(7) -0.0017(5) 0.0278(6) -0.0013(5)
O1 0.0826(10) 0.0801(10) 0.0732(9) -0.0306(7) 0.0552(8) -0.0313(8)
C12 0.0473(10) 0.0461(10) 0.0723(12) 0.0057(8) 0.0240(9) -0.0082(8)
C1 0.0399(8) 0.0373(8) 0.0428(8) 0.0018(6) 0.0219(7) 0.0021(6)
N3 0.0634(10) 0.0558(9) 0.0773(11) 0.0085(8) 0.0424(9) -0.0052(8)
C2 0.0537(10) 0.0373(8) 0.0559(10) -0.0041(7) 0.0299(8) -0.0012(7)
C11 0.0456(10) 0.0420(9) 0.0552(10) 0.0013(7) 0.0208(8) -0.0028(7)
C15 0.0355(8) 0.0345(8) 0.0395(8) 0.0015(6) 0.0193(7) 0.0030(6)
C22 0.0459(9) 0.0404(8) 0.0492(9) 0.0024(7) 0.0255(8) 0.0032(7)
C16 0.0379(8) 0.0374(8) 0.0428(8) -0.0009(6) 0.0241(7) -0.0014(6)
C10 0.0400(9) 0.0368(8) 0.0522(9) 0.0025(7) 0.0244(7) 0.0027(6)
C7 0.0405(8) 0.0398(8) 0.0427(8) -0.0003(6) 0.0225(7) 0.0013(6)
C4 0.0527(10) 0.0561(10) 0.0483(9) -0.0045(8) 0.0316(8) 0.0057(8)
C21 0.0520(10) 0.0514(10) 0.0502(10) 0.0077(7) 0.0258(8) 0.0004(8)
C14 0.0550(11) 0.0499(10) 0.0587(10) -0.0081(8) 0.0344(9) -0.0088(8)
C18 0.0328(8) 0.0445(9) 0.0416(8) -0.0081(7) 0.0180(7) -0.0019(6)
C17 0.0379(8) 0.0368(8) 0.0488(9) -0.0027(7) 0.0224(7) -0.0007(6)
C19 0.0386(9) 0.0606(10) 0.0449(9) -0.0094(7) 0.0242(7) -0.0038(7)
C9 0.0445(9) 0.0459(9) 0.0493(9) -0.0025(7) 0.0270(8) -0.0019(7)
C8 0.0498(10) 0.0426(9) 0.0515(9) -0.0035(7) 0.0309(8) -0.0044(7)
C6 0.0366(8) 0.0355(8) 0.0392(8) 0.0005(6) 0.0201(7) 0.0026(6)
C20 0.0473(10) 0.0667(11) 0.0459(9) -0.0003(8) 0.0269(8) -0.0084(8)
C5 0.0435(9) 0.0488(9) 0.0474(9) -0.0004(7) 0.0287(8) 0.0005(7)
C13 0.0662(12) 0.0640(12) 0.0655(12) -0.0021(9) 0.0432(10) -0.0072(9)
O4 0.0767(10) 0.0635(9) 0.0779(10) 0.0069(7) 0.0465(9) 0.0035(7)
O3 0.0663(9) 0.0472(8) 0.1101(12) 0.0015(7) 0.0577(9) 0.0093(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
O2 C17 1.2541(18) . ?
N1 C5 1.373(2) . ?
N1 C1 1.3844(19) . ?
N1 C6 1.4024(18) . ?
C3 C2 1.354(2) . ?
C3 C4 1.401(3) . ?
C3 H3 0.9300 . ?
N5 C18 1.348(2) . ?
N5 C17 1.397(2) . ?
N5 H5 0.8600 . ?
N4 C22 1.370(2) . ?
N4 C18 1.3710(19) . ?
N4 C16 1.4056(18) . ?
N2 C1 1.3385(19) . ?
N2 C15 1.3604(19) . ?
O1 C9 1.225(2) . ?
C12 N3 1.331(3) . ?
C12 C11 1.379(3) . ?
C12 H12 0.9300 . ?
C1 C2 1.400(2) . ?
N3 C13 1.335(3) . ?
C2 H2 0.9300 . ?
C11 C10 1.383(2) . ?
C11 H11 0.9300 . ?
C15 C6 1.403(2) . ?
C15 C16 1.439(2) . ?
C22 C21 1.356(2) . ?
C22 H22 0.9300 . ?
C16 C17 1.403(2) . ?
C10 C14 1.385(2) . ?
C10 C9 1.502(2) . ?
C7 C8 1.343(2) . ?
C7 C6 1.418(2) . ?
C7 H7 0.9300 . ?
C4 C5 1.353(2) . ?
C4 H4 0.9300 . ?
C21 C20 1.392(2) . ?
C21 H21 0.9300 . ?
C14 C13 1.376(3) . ?
C14 H14 0.9300 . ?
C18 C19 1.387(2) . ?
C19 C20 1.369(2) . ?
C19 H19 0.9300 . ?
C9 C8 1.454(2) . ?
C8 H8 0.9300 . ?
C20 H20 0.9300 . ?
C5 H5A 0.9300 . ?
C13 H13 0.9300 . ?
O4 H4A 0.899(17) . ?
O4 H4B 0.911(19) . ?
O3 H3A 0.887(17) . ?
O3 H3B 0.886(18) . ?
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
C5 N1 C1 120.77(13) . . ?
C5 N1 C6 132.16(13) . . ?
C1 N1 C6 107.05(12) . . ?
C2 C3 C4 120.19(15) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C18 N5 C17 111.10(12) . . ?
C18 N5 H5 124.5 . . ?
C17 N5 H5 124.5 . . ?
C22 N4 C18 120.39(13) . . ?
C22 N4 C16 130.35(12) . . ?
C18 N4 C16 109.16(12) . . ?
C1 N2 C15 105.80(12) . . ?
N3 C12 C11 124.14(17) . . ?
N3 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
N2 C1 N1 111.35(12) . . ?
N2 C1 C2 128.99(14) . . ?
N1 C1 C2 119.66(14) . . ?
C12 N3 C13 116.01(16) . . ?
C3 C2 C1 119.13(15) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C12 C11 C10 119.29(17) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
N2 C15 C6 111.59(12) . . ?
N2 C15 C16 120.61(13) . . ?
C6 C15 C16 127.77(13) . . ?
C21 C22 N4 118.90(15) . . ?
C21 C22 H22 120.5 . . ?
N4 C22 H22 120.5 . . ?
C17 C16 N4 106.89(12) . . ?
C17 C16 C15 129.79(13) . . ?
N4 C16 C15 121.75(13) . . ?
C11 C10 C14 117.09(15) . . ?
C11 C10 C9 119.95(15) . . ?
C14 C10 C9 122.95(15) . . ?
C8 C7 C6 131.29(15) . . ?
C8 C7 H7 114.4 . . ?
C6 C7 H7 114.4 . . ?
C5 C4 C3 121.11(15) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C22 C21 C20 121.49(16) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C13 C14 C10 119.44(17) . . ?
C13 C14 H14 120.3 . . ?
C10 C14 H14 120.3 . . ?
N5 C18 N4 107.20(13) . . ?
N5 C18 C19 131.72(14) . . ?
N4 C18 C19 121.08(14) . . ?
O2 C17 N5 123.50(14) . . ?
O2 C17 C16 130.83(14) . . ?
N5 C17 C16 105.66(12) . . ?
C20 C19 C18 118.34(15) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
O1 C9 C8 123.16(15) . . ?
O1 C9 C10 118.49(15) . . ?
C8 C9 C10 118.34(14) . . ?
C7 C8 C9 122.57(15) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
N1 C6 C15 104.18(12) . . ?
N1 C6 C7 127.75(13) . . ?
C15 C6 C7 127.69(13) . . ?
C19 C20 C21 119.78(15) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C4 C5 N1 119.11(15) . . ?
C4 C5 H5A 120.4 . . ?
N1 C5 H5A 120.4 . . ?
N3 C13 C14 123.96(18) . . ?
N3 C13 H13 118.0 . . ?
C14 C13 H13 118.0 . . ?
H4A O4 H4B 105(3) . . ?
H3A O3 H3B 108(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
C15 N2 C1 N1 -0.85(17) . . . . ?
C15 N2 C1 C2 -179.84(16) . . . . ?
C5 N1 C1 N2 -176.81(13) . . . . ?
C6 N1 C1 N2 1.69(17) . . . . ?
C5 N1 C1 C2 2.3(2) . . . . ?
C6 N1 C1 C2 -179.22(14) . . . . ?
C11 C12 N3 C13 1.4(3) . . . . ?
C4 C3 C2 C1 -0.1(3) . . . . ?
N2 C1 C2 C3 177.78(16) . . . . ?
N1 C1 C2 C3 -1.1(2) . . . . ?
N3 C12 C11 C10 1.3(3) . . . . ?
C1 N2 C15 C6 -0.32(17) . . . . ?
C1 N2 C15 C16 177.92(14) . . . . ?
C18 N4 C22 C21 1.7(2) . . . . ?
C16 N4 C22 C21 177.63(15) . . . . ?
C22 N4 C16 C17 -176.95(15) . . . . ?
C18 N4 C16 C17 -0.62(16) . . . . ?
C22 N4 C16 C15 16.1(2) . . . . ?
C18 N4 C16 C15 -167.61(13) . . . . ?
N2 C15 C16 C17 -132.51(17) . . . . ?
C6 C15 C16 C17 45.4(3) . . . . ?
N2 C15 C16 N4 31.2(2) . . . . ?
C6 C15 C16 N4 -150.85(15) . . . . ?
C12 C11 C10 C14 -2.6(2) . . . . ?
C12 C11 C10 C9 178.62(15) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
N4 C22 C21 C20 -0.6(3) . . . . ?
C11 C10 C14 C13 1.4(3) . . . . ?
C9 C10 C14 C13 -179.93(17) . . . . ?
C17 N5 C18 N4 -0.37(17) . . . . ?
C17 N5 C18 C19 178.61(16) . . . . ?
C22 N4 C18 N5 177.37(13) . . . . ?
C16 N4 C18 N5 0.61(16) . . . . ?
C22 N4 C18 C19 -1.7(2) . . . . ?
C16 N4 C18 C19 -178.50(13) . . . . ?
C18 N5 C17 O2 178.82(14) . . . . ?
C18 N5 C17 C16 -0.02(17) . . . . ?
N4 C16 C17 O2 -178.34(16) . . . . ?
C15 C16 C17 O2 -12.8(3) . . . . ?
N4 C16 C17 N5 0.39(16) . . . . ?
C15 C16 C17 N5 165.96(15) . . . . ?
N5 C18 C19 C20 -178.08(16) . . . . ?
N4 C18 C19 C20 0.8(2) . . . . ?
C11 C10 C9 O1 16.8(2) . . . . ?
C14 C10 C9 O1 -161.87(17) . . . . ?
C11 C10 C9 C8 -162.17(15) . . . . ?
C14 C10 C9 C8 19.2(2) . . . . ?
C6 C7 C8 C9 -174.67(16) . . . . ?
O1 C9 C8 C7 5.5(3) . . . . ?
C10 C9 C8 C7 -175.55(15) . . . . ?
C5 N1 C6 C15 176.52(15) . . . . ?
C1 N1 C6 C15 -1.75(15) . . . . ?
C5 N1 C6 C7 -10.2(3) . . . . ?
C1 N1 C6 C7 171.56(15) . . . . ?
N2 C15 C6 N1 1.31(16) . . . . ?
C16 C15 C6 N1 -176.78(14) . . . . ?
N2 C15 C6 C7 -172.00(14) . . . . ?
C16 C15 C6 C7 9.9(3) . . . . ?
C8 C7 C6 N1 7.6(3) . . . . ?
C8 C7 C6 C15 179.37(17) . . . . ?
C18 C19 C20 C21 0.2(2) . . . . ?
C22 C21 C20 C19 -0.3(3) . . . . ?
C3 C4 C5 N1 0.8(3) . . . . ?
C1 N1 C5 C4 -2.1(2) . . . . ?
C6 N1 C5 C4 179.82(15) . . . . ?
C12 N3 C13 C14 -2.8(3) . . . . ?
C10 C14 C13 N3 1.4(3) . . . . ?
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
N5 H5 O3 0.86 1.94 2.7492(17) 155.3 5_566
O3 H3A O2 0.887(17) 1.899(18) 2.7700(17) 167(2) .
O4 H4A O1 0.899(17) 1.930(18) 2.829(2) 178(3) 6_565
O3 H3B N2 0.886(18) 2.092(18) 2.9753(19) 175(3) 1_565
O4 H4B O2 0.911(19) 1.984(19) 2.889(2) 172(3) 6_565
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        62.76
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.035
#===END