# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2008


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Min Shi'
_publ_contact_author_email       MSHI@MAIL.SIOC.AC.CN

_publ_section_title              
;
A Convenient Three-Component Reaction Leading to the
Synthesis of Polysubstituted Cyclohexene Derivatives
;
loop_
_publ_author_name
'Min Shi.'
'Xiao-Yang Guan.'

# Attachment 'cd28232.cif'

data_cd28232
_database_code_depnum_ccdc_archive 'CCDC 688759'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 N5 O2'
_chemical_formula_weight         369.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   13.2254(13)
_cell_length_b                   11.3377(12)
_cell_length_c                   14.1441(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.874(2)
_cell_angle_gamma                90.00
_cell_volume                     1874.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1714
_cell_measurement_theta_min      4.850
_cell_measurement_theta_max      42.785

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.051
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.86356
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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            10802
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         26.99
_reflns_number_total             4078
_reflns_number_gt                2733
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0363P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4078
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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
N1 N 0.22827(16) 0.42903(16) 0.30156(15) 0.0562(5) Uani 1 1 d . . .
N2 N 0.45894(16) 0.15244(17) 0.32992(15) 0.0640(6) Uani 1 1 d . . .
N3 N 0.12857(16) 0.17565(17) 0.15552(16) 0.0418(5) Uani 1 1 d . . .
N4 N 0.03163(15) 0.04085(16) -0.09619(14) 0.0529(5) Uani 1 1 d . . .
N5 N 0.44638(16) 0.34339(15) 0.02372(16) 0.0435(4) Uani 1 1 d . . .
O1 O 0.54836(13) 0.34564(15) 0.08301(14) 0.0703(5) Uani 1 1 d . . .
O2 O 0.39940(15) 0.38957(15) -0.06346(14) 0.0689(5) Uani 1 1 d . . .
C1 C 0.35623(15) 0.36552(15) 0.14026(14) 0.0320(4) Uani 1 1 d . . .
H1 H 0.4324 0.3869 0.1968 0.038 Uiso 1 1 calc R . .
C2 C 0.29821(15) 0.29178(16) 0.19520(14) 0.0319(4) Uani 1 1 d . . .
C3 C 0.19992(14) 0.21311(15) 0.11763(14) 0.0298(4) Uani 1 1 d . . .
C4 C 0.19105(15) 0.18441(15) 0.02152(14) 0.0311(4) Uani 1 1 d . . .
C5 C 0.26623(15) 0.23041(16) -0.02535(14) 0.0323(4) Uani 1 1 d . . .
H5 H 0.2255 0.2940 -0.0758 0.039 Uiso 1 1 calc R . .
C6 C 0.37486(15) 0.28042(16) 0.06516(14) 0.0326(4) Uani 1 1 d . . .
H6 H 0.4200 0.2138 0.1085 0.039 Uiso 1 1 calc R . .
C7 C 0.25873(16) 0.37094(17) 0.25460(15) 0.0371(5) Uani 1 1 d . . .
C8 C 0.38710(17) 0.21198(18) 0.27366(16) 0.0392(5) Uani 1 1 d . . .
C9 C 0.10235(17) 0.10492(17) -0.04405(15) 0.0357(5) Uani 1 1 d . . .
C10 C 0.29652(17) 0.47996(16) 0.09029(15) 0.0345(5) Uani 1 1 d . . .
C11 C 0.17974(18) 0.48957(18) 0.02456(16) 0.0447(5) Uani 1 1 d . . .
H11 H 0.1335 0.4231 0.0091 0.054 Uiso 1 1 calc R . .
C12 C 0.1316(2) 0.5976(2) -0.01808(18) 0.0579(6) Uani 1 1 d . . .
H12 H 0.0532 0.6033 -0.0625 0.070 Uiso 1 1 calc R . .
C13 C 0.1989(3) 0.6968(2) 0.0047(2) 0.0667(7) Uani 1 1 d . . .
H13 H 0.1661 0.7694 -0.0236 0.080 Uiso 1 1 calc R . .
C14 C 0.3143(3) 0.6879(2) 0.0693(2) 0.0625(7) Uani 1 1 d . . .
H14 H 0.3599 0.7549 0.0848 0.075 Uiso 1 1 calc R . .
C15 C 0.3635(2) 0.58071(18) 0.11149(17) 0.0467(6) Uani 1 1 d . . .
H15 H 0.4422 0.5756 0.1545 0.056 Uiso 1 1 calc R . .
C16 C 0.29476(16) 0.13400(17) -0.08442(15) 0.0359(5) Uani 1 1 d . . .
C17 C 0.33217(18) 0.02514(18) -0.03902(18) 0.0478(6) Uani 1 1 d . . .
H17 H 0.3378 0.0087 0.0277 0.057 Uiso 1 1 calc R . .
C18 C 0.3615(2) -0.0603(2) -0.0915(2) 0.0619(7) Uani 1 1 d . . .
H18 H 0.3868 -0.1338 -0.0599 0.074 Uiso 1 1 calc R . .
C19 C 0.3536(2) -0.0376(2) -0.1893(2) 0.0672(7) Uani 1 1 d . . .
H19 H 0.3740 -0.0950 -0.2242 0.081 Uiso 1 1 calc R . .
C20 C 0.3159(2) 0.0696(3) -0.2355(2) 0.0777(8) Uani 1 1 d . . .
H20 H 0.3102 0.0851 -0.3024 0.093 Uiso 1 1 calc R . .
C21 C 0.2859(2) 0.1553(2) -0.18413(17) 0.0598(7) Uani 1 1 d . . .
H21 H 0.2596 0.2281 -0.2168 0.072 Uiso 1 1 calc R . .
H3A H 0.0835(16) 0.1160(18) 0.1231(16) 0.044(6) Uiso 1 1 d . . .
H3B H 0.1458(17) 0.1846(19) 0.2230(18) 0.059(7) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0788(14) 0.0447(11) 0.0585(13) -0.0068(10) 0.0432(12) -0.0037(10)
N2 0.0594(12) 0.0599(13) 0.0519(13) 0.0119(11) 0.0087(10) 0.0051(11)
N3 0.0488(11) 0.0418(11) 0.0406(12) -0.0079(9) 0.0257(10) -0.0168(9)
N4 0.0521(12) 0.0553(12) 0.0466(12) -0.0103(10) 0.0192(10) -0.0202(10)
N5 0.0495(11) 0.0344(10) 0.0591(12) -0.0076(9) 0.0359(10) -0.0078(9)
O1 0.0411(10) 0.0735(12) 0.1008(14) -0.0010(11) 0.0369(10) -0.0122(9)
O2 0.0824(12) 0.0733(12) 0.0604(11) 0.0128(10) 0.0413(10) -0.0177(10)
C1 0.0312(10) 0.0296(10) 0.0329(11) -0.0026(9) 0.0130(9) -0.0067(8)
C2 0.0364(10) 0.0282(10) 0.0303(10) -0.0012(9) 0.0148(9) -0.0024(9)
C3 0.0308(10) 0.0252(10) 0.0321(10) 0.0017(8) 0.0136(9) -0.0018(8)
C4 0.0321(10) 0.0260(10) 0.0311(10) -0.0012(8) 0.0114(9) -0.0024(8)
C5 0.0372(10) 0.0293(10) 0.0298(10) 0.0017(9) 0.0151(9) -0.0001(9)
C6 0.0361(10) 0.0267(10) 0.0360(11) 0.0009(9) 0.0176(9) -0.0024(9)
C7 0.0455(12) 0.0314(11) 0.0354(11) -0.0027(9) 0.0197(10) -0.0080(10)
C8 0.0432(12) 0.0363(12) 0.0318(11) 0.0001(10) 0.0123(10) -0.0061(10)
C9 0.0380(11) 0.0373(11) 0.0309(11) 0.0010(9) 0.0153(9) -0.0029(9)
C10 0.0497(12) 0.0282(10) 0.0341(11) -0.0025(9) 0.0267(10) -0.0035(9)
C11 0.0518(13) 0.0360(12) 0.0462(13) 0.0013(10) 0.0228(11) 0.0025(10)
C12 0.0727(16) 0.0526(15) 0.0535(15) 0.0112(13) 0.0337(13) 0.0225(14)
C13 0.116(2) 0.0366(14) 0.0679(18) 0.0147(13) 0.0600(18) 0.0219(16)
C14 0.106(2) 0.0323(13) 0.0719(18) -0.0016(13) 0.0610(18) -0.0087(14)
C15 0.0670(15) 0.0369(12) 0.0508(14) -0.0061(11) 0.0397(12) -0.0107(11)
C16 0.0405(11) 0.0338(11) 0.0342(11) -0.0049(9) 0.0182(9) -0.0044(9)
C17 0.0637(14) 0.0373(12) 0.0511(14) -0.0010(11) 0.0342(12) 0.0020(11)
C18 0.0763(17) 0.0426(14) 0.0759(18) -0.0069(13) 0.0433(15) 0.0057(13)
C19 0.0777(18) 0.0611(18) 0.0730(19) -0.0238(15) 0.0439(16) 0.0000(15)
C20 0.110(2) 0.086(2) 0.0485(16) -0.0104(16) 0.0466(16) 0.0126(19)
C21 0.0880(18) 0.0560(15) 0.0412(13) 0.0046(12) 0.0350(13) 0.0149(14)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.135(2) . ?
N2 C8 1.133(2) . ?
N3 C3 1.353(2) . ?
N3 H3A 0.88(2) . ?
N3 H3B 0.88(2) . ?
N4 C9 1.141(2) . ?
N5 O2 1.210(2) . ?
N5 O1 1.211(2) . ?
N5 C6 1.505(2) . ?
C1 C10 1.512(2) . ?
C1 C6 1.538(2) . ?
C1 C2 1.565(2) . ?
C1 H1 0.9800 . ?
C2 C7 1.481(3) . ?
C2 C8 1.487(3) . ?
C2 C3 1.535(2) . ?
C3 C4 1.349(2) . ?
C4 C9 1.425(3) . ?
C4 C5 1.522(2) . ?
C5 C6 1.518(2) . ?
C5 C16 1.526(2) . ?
C5 H5 0.9800 . ?
C6 H6 0.9800 . ?
C10 C11 1.385(3) . ?
C10 C15 1.389(2) . ?
C11 C12 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.372(3) . ?
C16 C21 1.381(3) . ?
C17 C18 1.382(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.362(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.359(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(3) . ?
C20 H20 0.9300 . ?
C21 H21 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
C3 N3 H3A 117.6(12) . . ?
C3 N3 H3B 121.4(14) . . ?
H3A N3 H3B 115.2(19) . . ?
O2 N5 O1 124.88(18) . . ?
O2 N5 C6 119.02(17) . . ?
O1 N5 C6 116.08(18) . . ?
C10 C1 C6 115.65(15) . . ?
C10 C1 C2 114.87(14) . . ?
C6 C1 C2 106.37(14) . . ?
C10 C1 H1 106.4 . . ?
C6 C1 H1 106.4 . . ?
C2 C1 H1 106.4 . . ?
C7 C2 C8 108.09(15) . . ?
C7 C2 C3 110.62(14) . . ?
C8 C2 C3 106.84(15) . . ?
C7 C2 C1 110.03(15) . . ?
C8 C2 C1 107.18(14) . . ?
C3 C2 C1 113.80(14) . . ?
C4 C3 N3 125.13(17) . . ?
C4 C3 C2 120.42(15) . . ?
N3 C3 C2 114.44(16) . . ?
C3 C4 C9 117.76(16) . . ?
C3 C4 C5 126.14(16) . . ?
C9 C4 C5 116.09(15) . . ?
C6 C5 C4 108.30(14) . . ?
C6 C5 C16 110.51(14) . . ?
C4 C5 C16 111.84(15) . . ?
C6 C5 H5 108.7 . . ?
C4 C5 H5 108.7 . . ?
C16 C5 H5 108.7 . . ?
N5 C6 C5 111.59(15) . . ?
N5 C6 C1 107.71(14) . . ?
C5 C6 C1 115.01(14) . . ?
N5 C6 H6 107.4 . . ?
C5 C6 H6 107.4 . . ?
C1 C6 H6 107.4 . . ?
N1 C7 C2 178.2(2) . . ?
N2 C8 C2 175.4(2) . . ?
N4 C9 C4 179.7(3) . . ?
C11 C10 C15 118.58(19) . . ?
C11 C10 C1 123.79(17) . . ?
C15 C10 C1 117.63(18) . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C17 C16 C21 118.38(19) . . ?
C17 C16 C5 121.01(17) . . ?
C21 C16 C5 120.59(18) . . ?
C16 C17 C18 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.7(2) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.5(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 120.5(2) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?

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
C10 C1 C2 C7 -40.9(2) . . . . ?
C6 C1 C2 C7 -170.18(14) . . . . ?
C10 C1 C2 C8 -158.18(15) . . . . ?
C6 C1 C2 C8 72.51(17) . . . . ?
C10 C1 C2 C3 83.92(19) . . . . ?
C6 C1 C2 C3 -45.39(19) . . . . ?
C7 C2 C3 C4 143.89(17) . . . . ?
C8 C2 C3 C4 -98.68(19) . . . . ?
C1 C2 C3 C4 19.4(2) . . . . ?
C7 C2 C3 N3 -37.5(2) . . . . ?
C8 C2 C3 N3 79.96(19) . . . . ?
C1 C2 C3 N3 -161.95(16) . . . . ?
N3 C3 C4 C9 -2.5(3) . . . . ?
C2 C3 C4 C9 175.99(16) . . . . ?
N3 C3 C4 C5 176.55(17) . . . . ?
C2 C3 C4 C5 -5.0(3) . . . . ?
C3 C4 C5 C6 18.4(2) . . . . ?
C9 C4 C5 C6 -162.53(16) . . . . ?
C3 C4 C5 C16 140.43(18) . . . . ?
C9 C4 C5 C16 -40.5(2) . . . . ?
O2 N5 C6 C5 29.3(2) . . . . ?
O1 N5 C6 C5 -152.22(17) . . . . ?
O2 N5 C6 C1 -97.8(2) . . . . ?
O1 N5 C6 C1 80.6(2) . . . . ?
C4 C5 C6 N5 -171.84(14) . . . . ?
C16 C5 C6 N5 65.33(19) . . . . ?
C4 C5 C6 C1 -48.8(2) . . . . ?
C16 C5 C6 C1 -171.61(15) . . . . ?
C10 C1 C6 N5 59.6(2) . . . . ?
C2 C1 C6 N5 -171.57(15) . . . . ?
C10 C1 C6 C5 -65.5(2) . . . . ?
C2 C1 C6 C5 63.32(19) . . . . ?
C8 C2 C7 N1 -46(7) . . . . ?
C3 C2 C7 N1 70(7) . . . . ?
C1 C2 C7 N1 -163(7) . . . . ?
C7 C2 C8 N2 -137(3) . . . . ?
C3 C2 C8 N2 104(3) . . . . ?
C1 C2 C8 N2 -18(3) . . . . ?
C3 C4 C9 N4 -70(40) . . . . ?
C5 C4 C9 N4 111(40) . . . . ?
C6 C1 C10 C11 77.2(2) . . . . ?
C2 C1 C10 C11 -47.4(2) . . . . ?
C6 C1 C10 C15 -102.46(19) . . . . ?
C2 C1 C10 C15 132.98(17) . . . . ?
C15 C10 C11 C12 -0.4(3) . . . . ?
C1 C10 C11 C12 -179.99(18) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C10 -0.8(3) . . . . ?
C11 C10 C15 C14 1.0(3) . . . . ?
C1 C10 C15 C14 -179.37(18) . . . . ?
C6 C5 C16 C17 73.3(2) . . . . ?
C4 C5 C16 C17 -47.5(2) . . . . ?
C6 C5 C16 C21 -105.3(2) . . . . ?
C4 C5 C16 C21 133.99(19) . . . . ?
C21 C16 C17 C18 0.8(3) . . . . ?
C5 C16 C17 C18 -177.79(18) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C20 -0.5(4) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C19 C20 C21 C16 0.5(4) . . . . ?
C17 C16 C21 C20 -1.0(3) . . . . ?
C5 C16 C21 C20 177.5(2) . . . . ?

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
N3 H3A N4 0.88(2) 2.26(2) 3.091(3) 159.6(17) 3

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036

# Attachment 'cd28234.cif'

data_cd28234
_database_code_depnum_ccdc_archive 'CCDC 688760'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 N5 O2.33'
_chemical_formula_weight         375.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Rhombohedral
_symmetry_space_group_name_H-M   R-3

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   23.2536(10)
_cell_length_b                   23.2536(10)
_cell_length_c                   17.7700(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     8321.4(7)
_cell_formula_units_Z            18
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3709
_cell_measurement_theta_min      5.011
_cell_measurement_theta_max      52.413

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.469
_exptl_crystal_size_mid          0.411
_exptl_crystal_size_min          0.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3522
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.75474
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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            16528
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4041
_reflns_number_gt                2779
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0730P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4041
_refine_ls_number_parameters     267
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1330
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.003
_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
N1 N -0.02012(9) 0.25265(9) 0.13883(10) 0.0556(5) Uani 1 1 d . . .
N2 N -0.06747(9) 0.26696(9) -0.09657(11) 0.0645(5) Uani 1 1 d . . .
N3 N -0.07325(8) 0.36373(10) 0.04624(12) 0.0545(5) Uani 1 1 d D . .
N4 N 0.01189(9) 0.53005(8) 0.10618(9) 0.0549(5) Uani 1 1 d . . .
N5 N 0.19753(7) 0.42961(7) 0.04304(10) 0.0443(4) Uani 1 1 d . . .
O1 O 0.23476(7) 0.45707(7) 0.09558(9) 0.0635(4) Uani 1 1 d . . .
O2 O 0.21525(7) 0.42389(7) -0.01920(9) 0.0617(4) Uani 1 1 d . . .
C1 C 0.08141(8) 0.35470(8) -0.00281(10) 0.0345(4) Uani 1 1 d . . .
H1 H 0.0899 0.3796 -0.0499 0.041 Uiso 1 1 calc R . .
C2 C 0.00684(8) 0.32812(8) 0.02018(9) 0.0335(4) Uani 1 1 d . . .
C3 C -0.00790(8) 0.38256(8) 0.04319(10) 0.0350(4) Uani 1 1 d . . .
C4 C 0.04159(8) 0.44202(8) 0.06490(9) 0.0349(4) Uani 1 1 d . . .
C5 C 0.11457(8) 0.46345(8) 0.06972(10) 0.0368(4) Uani 1 1 d . . .
H5 H 0.1283 0.4787 0.1215 0.044 Uiso 1 1 calc R . .
C6 C 0.12432(8) 0.40303(8) 0.05837(10) 0.0355(4) Uani 1 1 d . . .
H6 H 0.1134 0.3785 0.1060 0.043 Uiso 1 1 calc R . .
C7 C -0.01038(8) 0.28288(9) 0.08553(11) 0.0379(4) Uani 1 1 d . . .
C8 C -0.03537(9) 0.29190(9) -0.04529(11) 0.0401(4) Uani 1 1 d . . .
C9 C 0.02504(9) 0.49094(9) 0.08789(10) 0.0401(4) Uani 1 1 d . . .
C10 C 0.09291(8) 0.29631(8) -0.01719(10) 0.0379(4) Uani 1 1 d . . .
C11 C 0.08560(10) 0.27178(10) -0.08930(12) 0.0521(5) Uani 1 1 d . . .
H11 H 0.0752 0.2918 -0.1281 0.063 Uiso 1 1 calc R . .
C12 C 0.09351(11) 0.21773(11) -0.10489(15) 0.0664(6) Uani 1 1 d . . .
H12 H 0.0878 0.2015 -0.1538 0.080 Uiso 1 1 calc R . .
C13 C 0.10963(11) 0.18835(11) -0.04848(16) 0.0650(7) Uani 1 1 d . . .
H13 H 0.1149 0.1520 -0.0588 0.078 Uiso 1 1 calc R . .
C14 C 0.11800(10) 0.21261(11) 0.02308(14) 0.0607(6) Uani 1 1 d . . .
H14 H 0.1297 0.1930 0.0612 0.073 Uiso 1 1 calc R . .
C15 C 0.10934(9) 0.26623(9) 0.03975(12) 0.0478(5) Uani 1 1 d . . .
H15 H 0.1145 0.2819 0.0889 0.057 Uiso 1 1 calc R . .
C16 C 0.15516(8) 0.52333(8) 0.01909(11) 0.0403(5) Uani 1 1 d . . .
C17 C 0.14935(10) 0.52057(10) -0.05832(12) 0.0560(5) Uani 1 1 d . . .
H17 H 0.1205 0.4805 -0.0815 0.067 Uiso 1 1 calc R . .
C18 C 0.18558(12) 0.57616(12) -0.10140(15) 0.0705(7) Uani 1 1 d . . .
H18 H 0.1816 0.5728 -0.1535 0.085 Uiso 1 1 calc R . .
C19 C 0.22692(12) 0.63582(13) -0.0699(2) 0.0785(8) Uani 1 1 d . . .
H19 H 0.2513 0.6730 -0.0999 0.094 Uiso 1 1 calc R . .
C20 C 0.23230(11) 0.64063(11) 0.0068(2) 0.0791(9) Uani 1 1 d . . .
H20 H 0.2597 0.6816 0.0292 0.095 Uiso 1 1 calc R . .
C21 C 0.19677(10) 0.58415(10) 0.05201(14) 0.0593(6) Uani 1 1 d . . .
H21 H 0.2012 0.5876 0.1041 0.071 Uiso 1 1 calc R . .
H3A H -0.0999(9) 0.3324(9) 0.0211(11) 0.054(7) Uiso 1 1 d D . .
H3B H -0.0817(11) 0.3946(10) 0.0589(13) 0.073(8) Uiso 1 1 d D . .
O3 O 1.0000 1.0000 0.9509(7) 0.165(7) Uiso 1 3 d SD . .
H3C H 0.9649(11) 0.9530(11) 0.9249(14) 0.093(8) 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
N1 0.0656(12) 0.0552(11) 0.0487(11) 0.0101(8) 0.0090(9) 0.0322(9)
N2 0.0509(11) 0.0714(13) 0.0531(12) -0.0090(9) -0.0135(9) 0.0170(9)
N3 0.0316(9) 0.0453(11) 0.0850(14) -0.0093(10) -0.0012(9) 0.0179(9)
N4 0.0659(12) 0.0573(11) 0.0525(11) -0.0068(8) 0.0008(8) 0.0389(10)
N5 0.0337(9) 0.0375(9) 0.0603(12) 0.0055(8) -0.0025(8) 0.0167(7)
O1 0.0395(8) 0.0631(10) 0.0760(11) -0.0013(8) -0.0226(7) 0.0167(7)
O2 0.0427(8) 0.0667(10) 0.0687(11) 0.0012(8) 0.0124(7) 0.0220(7)
C1 0.0318(9) 0.0348(9) 0.0361(10) 0.0028(7) 0.0017(7) 0.0162(8)
C2 0.0303(9) 0.0330(9) 0.0345(9) -0.0005(7) -0.0023(7) 0.0136(7)
C3 0.0305(9) 0.0372(10) 0.0381(10) 0.0037(7) 0.0014(7) 0.0175(8)
C4 0.0349(9) 0.0364(9) 0.0346(10) 0.0002(7) 0.0027(7) 0.0188(8)
C5 0.0353(9) 0.0368(10) 0.0355(10) -0.0064(7) -0.0050(7) 0.0159(8)
C6 0.0280(9) 0.0377(10) 0.0386(10) 0.0019(7) -0.0018(7) 0.0147(8)
C7 0.0355(10) 0.0362(10) 0.0403(11) -0.0023(8) 0.0009(8) 0.0166(8)
C8 0.0320(9) 0.0410(10) 0.0412(11) 0.0014(8) -0.0002(8) 0.0137(8)
C9 0.0411(10) 0.0412(10) 0.0380(10) -0.0002(8) 0.0021(8) 0.0204(9)
C10 0.0298(9) 0.0353(9) 0.0479(11) -0.0019(8) 0.0016(7) 0.0157(8)
C11 0.0593(13) 0.0534(12) 0.0494(13) -0.0038(9) 0.0006(9) 0.0325(11)
C12 0.0728(16) 0.0617(14) 0.0709(16) -0.0158(12) 0.0062(12) 0.0384(13)
C13 0.0597(14) 0.0510(13) 0.094(2) -0.0023(13) 0.0164(13) 0.0347(12)
C14 0.0545(13) 0.0558(13) 0.0842(18) 0.0167(12) 0.0107(12) 0.0370(11)
C15 0.0450(11) 0.0491(11) 0.0549(13) 0.0030(9) 0.0027(9) 0.0277(10)
C16 0.0301(9) 0.0318(10) 0.0605(13) -0.0041(8) 0.0012(8) 0.0165(8)
C17 0.0591(13) 0.0419(11) 0.0607(14) 0.0078(10) 0.0023(10) 0.0205(10)
C18 0.0679(16) 0.0602(15) 0.0837(18) 0.0263(13) 0.0153(13) 0.0323(13)
C19 0.0510(15) 0.0553(16) 0.133(3) 0.0355(16) 0.0268(15) 0.0294(13)
C20 0.0414(13) 0.0316(12) 0.153(3) -0.0099(15) 0.0041(15) 0.0101(10)
C21 0.0406(11) 0.0448(12) 0.0881(17) -0.0155(11) -0.0013(11) 0.0181(10)

_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
N1 C7 1.133(2) . ?
N2 C8 1.136(2) . ?
N3 C3 1.356(2) . ?
N3 H3A 0.814(15) . ?
N3 H3B 0.863(16) . ?
N4 C9 1.142(2) . ?
N5 O2 1.211(2) . ?
N5 O1 1.215(2) . ?
N5 C6 1.517(2) . ?
C1 C6 1.523(2) . ?
C1 C10 1.531(2) . ?
C1 C2 1.576(2) . ?
C1 H1 0.9800 . ?
C2 C7 1.481(2) . ?
C2 C8 1.483(2) . ?
C2 C3 1.524(2) . ?
C3 C4 1.339(2) . ?
C4 C9 1.431(2) . ?
C4 C5 1.513(2) . ?
C5 C16 1.525(2) . ?
C5 C6 1.544(2) . ?
C5 H5 0.9800 . ?
C6 H6 0.9800 . ?
C10 C11 1.378(3) . ?
C10 C15 1.388(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.381(3) . ?
C16 C21 1.382(3) . ?
C17 C18 1.370(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.353(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.402(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
O3 O3 1.75(3) 10_777 ?
O3 H3C 1.086(17) . ?

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
C3 N3 H3A 119.8(15) . . ?
C3 N3 H3B 115.2(15) . . ?
H3A N3 H3B 120(2) . . ?
O2 N5 O1 124.57(16) . . ?
O2 N5 C6 119.57(15) . . ?
O1 N5 C6 115.84(17) . . ?
C6 C1 C10 115.68(14) . . ?
C6 C1 C2 106.89(13) . . ?
C10 C1 C2 109.95(13) . . ?
C6 C1 H1 108.0 . . ?
C10 C1 H1 108.0 . . ?
C2 C1 H1 108.0 . . ?
C7 C2 C8 110.15(14) . . ?
C7 C2 C3 106.65(13) . . ?
C8 C2 C3 108.81(14) . . ?
C7 C2 C1 109.60(13) . . ?
C8 C2 C1 107.78(14) . . ?
C3 C2 C1 113.84(13) . . ?
C4 C3 N3 124.58(17) . . ?
C4 C3 C2 120.06(14) . . ?
N3 C3 C2 115.08(16) . . ?
C3 C4 C9 117.98(15) . . ?
C3 C4 C5 126.84(15) . . ?
C9 C4 C5 115.16(15) . . ?
C4 C5 C16 110.34(14) . . ?
C4 C5 C6 110.09(13) . . ?
C16 C5 C6 116.63(14) . . ?
C4 C5 H5 106.4 . . ?
C16 C5 H5 106.4 . . ?
C6 C5 H5 106.4 . . ?
N5 C6 C1 111.10(14) . . ?
N5 C6 C5 107.34(13) . . ?
C1 C6 C5 115.13(13) . . ?
N5 C6 H6 107.7 . . ?
C1 C6 H6 107.7 . . ?
C5 C6 H6 107.7 . . ?
N1 C7 C2 174.4(2) . . ?
N2 C8 C2 176.7(2) . . ?
N4 C9 C4 179.9(3) . . ?
C11 C10 C15 118.51(17) . . ?
C11 C10 C1 118.83(16) . . ?
C15 C10 C1 122.65(17) . . ?
C10 C11 C12 121.1(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.9(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C10 C15 C14 119.8(2) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C21 118.13(19) . . ?
C17 C16 C5 122.96(16) . . ?
C21 C16 C5 118.80(18) . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 121.5(3) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 119.1(2) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C19 C20 C21 120.5(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 119.9(2) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
O3 O3 H3C 115.1(19) 10_777 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C7 -71.35(17) . . . . ?
C10 C1 C2 C7 54.95(18) . . . . ?
C6 C1 C2 C8 168.77(14) . . . . ?
C10 C1 C2 C8 -64.93(17) . . . . ?
C6 C1 C2 C3 47.99(18) . . . . ?
C10 C1 C2 C3 174.29(13) . . . . ?
C7 C2 C3 C4 100.52(18) . . . . ?
C8 C2 C3 C4 -140.68(16) . . . . ?
C1 C2 C3 C4 -20.5(2) . . . . ?
C7 C2 C3 N3 -73.70(19) . . . . ?
C8 C2 C3 N3 45.1(2) . . . . ?
C1 C2 C3 N3 165.30(16) . . . . ?
N3 C3 C4 C9 -4.7(3) . . . . ?
C2 C3 C4 C9 -178.37(15) . . . . ?
N3 C3 C4 C5 173.75(18) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C16 120.80(19) . . . . ?
C9 C4 C5 C16 -60.68(19) . . . . ?
C3 C4 C5 C6 -9.3(2) . . . . ?
C9 C4 C5 C6 169.18(15) . . . . ?
O2 N5 C6 C1 16.6(2) . . . . ?
O1 N5 C6 C1 -165.06(14) . . . . ?
O2 N5 C6 C5 -110.09(17) . . . . ?
O1 N5 C6 C5 68.26(18) . . . . ?
C10 C1 C6 N5 54.97(19) . . . . ?
C2 C1 C6 N5 177.77(13) . . . . ?
C10 C1 C6 C5 177.25(14) . . . . ?
C2 C1 C6 C5 -59.95(18) . . . . ?
C4 C5 C6 N5 165.20(14) . . . . ?
C16 C5 C6 N5 38.51(19) . . . . ?
C4 C5 C6 C1 40.9(2) . . . . ?
C16 C5 C6 C1 -85.76(18) . . . . ?
C8 C2 C7 N1 -173.7(19) . . . . ?
C3 C2 C7 N1 -56(2) . . . . ?
C1 C2 C7 N1 68(2) . . . . ?
C7 C2 C8 N2 150(4) . . . . ?
C3 C2 C8 N2 33(4) . . . . ?
C1 C2 C8 N2 -91(4) . . . . ?
C3 C4 C9 N4 -134(100) . . . . ?
C5 C4 C9 N4 47(98) . . . . ?
C6 C1 C10 C11 -146.71(17) . . . . ?
C2 C1 C10 C11 92.12(19) . . . . ?
C6 C1 C10 C15 34.4(2) . . . . ?
C2 C1 C10 C15 -86.8(2) . . . . ?
C15 C10 C11 C12 0.9(3) . . . . ?
C1 C10 C11 C12 -178.06(18) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 1.0(3) . . . . ?
C11 C10 C15 C14 0.0(3) . . . . ?
C1 C10 C15 C14 178.89(16) . . . . ?
C13 C14 C15 C10 -0.9(3) . . . . ?
C4 C5 C16 C17 -65.3(2) . . . . ?
C6 C5 C16 C17 61.2(2) . . . . ?
C4 C5 C16 C21 110.64(18) . . . . ?
C6 C5 C16 C21 -122.80(18) . . . . ?
C21 C16 C17 C18 2.2(3) . . . . ?
C5 C16 C17 C18 178.19(18) . . . . ?
C16 C17 C18 C19 -1.6(3) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C18 C19 C20 C21 1.7(4) . . . . ?
C17 C16 C21 C20 -0.9(3) . . . . ?
C5 C16 C21 C20 -177.02(17) . . . . ?
C19 C20 C21 C16 -1.1(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
N3 H3A O2 0.814(15) 2.632(17) 3.346(2) 147.3(19) 12

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.042