# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2005



data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Ming-Wu Ding'
_publ_contact_author_address     
;
College of Chemistry
Central China Normal University
Wuhan
Hubei
430079
CHINA
;

_publ_contact_author_email       MWDING@MAIL.CCNU.EDU.CN

_publ_section_title              
;
Iminophosphorane-Mediated Efficient Synthesis of New
Tricyclic
3,5-Dihydro-1,2,3-triazolo[4,5-d]-1,2,4-triazolo[1,5-a]pyrimidin-9-ones
;
loop_
_publ_author_name
'Ming-Wu Ding'
'Wen-Jing Xiao'
'Chang Xie'
'Jun-Feng Zhao'

# Attachment '0704am.cif'

data_0704am
_database_code_depnum_ccdc_archive 'CCDC 279775'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 N9 O2'
_chemical_formula_weight         507.56

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   P21/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                   12.902(3)
_cell_length_b                   12.479(3)
_cell_length_c                   15.918(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.206(4)
_cell_angle_gamma                90.00
_cell_volume                     2522.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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            15362
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0685
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         28.28
_reflns_number_total             6082
_reflns_number_gt                3363
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0724P)^2^+0.2601P] 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         6082
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1382
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_ref         0.1785
_refine_ls_wR_factor_gt          0.1508
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.58599(19) 0.15265(19) -0.01518(15) 0.0391(6) Uani 1 1 d . . .
C2 C 0.62775(19) 0.0592(2) -0.04239(15) 0.0389(6) Uani 1 1 d . . .
C3 C 0.65823(19) -0.0289(2) 0.01456(16) 0.0414(6) Uani 1 1 d . . .
C4 C 0.59346(19) 0.09615(19) 0.11423(15) 0.0368(6) Uani 1 1 d . . .
C5 C 0.6233(2) -0.0116(2) 0.22670(16) 0.0402(6) Uani 1 1 d . . .
C6 C 0.6371(2) -0.1468(2) 0.34117(16) 0.0418(6) Uani 1 1 d . . .
C7 C 0.6311(2) -0.2371(2) 0.28995(17) 0.0451(6) Uani 1 1 d . . .
H7 H 0.6236 -0.2297 0.2310 0.054 Uiso 1 1 calc R . .
C8 C 0.6361(2) -0.3380(2) 0.32605(18) 0.0497(7) Uani 1 1 d . . .
H8A H 0.6312 -0.3982 0.2912 0.060 Uiso 1 1 calc R . .
C9 C 0.6485(2) -0.3503(2) 0.41329(18) 0.0523(7) Uani 1 1 d . . .
H9 H 0.6512 -0.4184 0.4373 0.063 Uiso 1 1 calc R . .
C10 C 0.6566(2) -0.2612(2) 0.46426(18) 0.0593(8) Uani 1 1 d . . .
H10 H 0.6662 -0.2691 0.5232 0.071 Uiso 1 1 calc R . .
C11 C 0.6508(2) -0.1597(2) 0.42922(17) 0.0559(8) Uani 1 1 d . . .
H11 H 0.6559 -0.0998 0.4645 0.067 Uiso 1 1 calc R . .
C12 C 0.5463(2) 0.17374(19) 0.24607(14) 0.0372(6) Uani 1 1 d . . .
C13 C 0.4414(2) 0.1761(2) 0.25103(17) 0.0499(7) Uani 1 1 d . . .
H13 H 0.3965 0.1220 0.2265 0.060 Uiso 1 1 calc R . .
C14 C 0.4033(2) 0.2609(2) 0.29332(18) 0.0552(8) Uani 1 1 d . . .
H14 H 0.3323 0.2625 0.2975 0.066 Uiso 1 1 calc R . .
C15 C 0.4683(2) 0.3429(2) 0.32927(16) 0.0452(7) Uani 1 1 d . . .
C16 C 0.5736(2) 0.3373(2) 0.32352(17) 0.0498(7) Uani 1 1 d . . .
H16 H 0.6188 0.3915 0.3476 0.060 Uiso 1 1 calc R . .
C17 C 0.6134(2) 0.2530(2) 0.28269(17) 0.0474(7) Uani 1 1 d . . .
H17 H 0.6847 0.2499 0.2800 0.057 Uiso 1 1 calc R . .
C18 C 0.4252(3) 0.4380(2) 0.3702(2) 0.0682(9) Uani 1 1 d . . .
H18A H 0.4588 0.4429 0.4290 0.102 Uiso 1 1 calc R . .
H18B H 0.3506 0.4295 0.3671 0.102 Uiso 1 1 calc R . .
H18C H 0.4386 0.5022 0.3408 0.102 Uiso 1 1 calc R . .
C19 C 0.5292(2) 0.3241(2) -0.09438(15) 0.0474(7) Uani 1 1 d . . .
C20 C 0.4324(2) 0.3426(2) -0.07328(17) 0.0559(8) Uani 1 1 d . . .
H20 H 0.3956 0.2877 -0.0521 0.067 Uiso 1 1 calc R . .
C21 C 0.3902(3) 0.4454(3) -0.08417(19) 0.0716(10) Uani 1 1 d . . .
H21 H 0.3246 0.4596 -0.0701 0.086 Uiso 1 1 calc R . .
C22 C 0.4446(4) 0.5257(3) -0.1154(2) 0.0841(12) Uani 1 1 d . . .
H22 H 0.4159 0.5941 -0.1228 0.101 Uiso 1 1 calc R . .
C23 C 0.5417(4) 0.5055(3) -0.1359(2) 0.0879(12) Uani 1 1 d . . .
H23 H 0.5786 0.5605 -0.1568 0.105 Uiso 1 1 calc R . .
C24 C 0.5855(3) 0.4033(3) -0.12586(19) 0.0678(9) Uani 1 1 d . . .
H24 H 0.6510 0.3891 -0.1401 0.081 Uiso 1 1 calc R . .
C25 C 0.3661(3) 0.8333(3) 0.4990(2) 0.0775(10) Uani 1 1 d . . .
H25 H 0.3642 0.7679 0.5268 0.093 Uiso 1 1 calc R . .
C26 C 0.3563(3) 0.7283(3) 0.3714(2) 0.0810(11) Uani 1 1 d . . .
H26A H 0.3606 0.6705 0.4117 0.122 Uiso 1 1 calc R . .
H26B H 0.4144 0.7240 0.3413 0.122 Uiso 1 1 calc R . .
H26C H 0.2913 0.7232 0.3314 0.122 Uiso 1 1 calc R . .
C27 C 0.3639(3) 0.9287(3) 0.3695(2) 0.0939(12) Uani 1 1 d . . .
H27A H 0.2938 0.9563 0.3527 0.141 Uiso 1 1 calc R . .
H27B H 0.3940 0.9147 0.3196 0.141 Uiso 1 1 calc R . .
H27C H 0.4064 0.9803 0.4048 0.141 Uiso 1 1 calc R . .
N1 N 0.57293(17) 0.21775(17) -0.08429(13) 0.0455(5) Uani 1 1 d . . .
N2 N 0.60598(19) 0.16621(19) -0.15137(14) 0.0525(6) Uani 1 1 d . . .
N3 N 0.63901(18) 0.07084(18) -0.12595(13) 0.0499(6) Uani 1 1 d . . .
N4 N 0.56676(16) 0.17801(16) 0.06380(12) 0.0407(5) Uani 1 1 d . . .
N5 N 0.63332(15) -0.00083(15) 0.09515(12) 0.0384(5) Uani 1 1 d . . .
N6 N 0.65351(17) -0.06886(16) 0.16637(13) 0.0435(5) Uani 1 1 d . . .
N7 N 0.58720(16) 0.08948(15) 0.19899(12) 0.0399(5) Uani 1 1 d . . .
N8 N 0.62484(18) -0.04137(17) 0.30827(13) 0.0474(6) Uani 1 1 d . . .
H8 H 0.6176 0.0087 0.3439 0.057 Uiso 1 1 calc R . .
N9 N 0.36009(19) 0.83058(19) 0.41669(15) 0.0561(6) Uani 1 1 d . . .
O1 O 0.69934(15) -0.11368(15) 0.00306(12) 0.0568(5) Uani 1 1 d . . .
O2 O 0.3741(3) 0.91349(19) 0.54306(15) 0.1053(10) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0444(15) 0.0340(14) 0.0395(14) 0.0010(11) 0.0094(11) -0.0014(11)
C2 0.0451(15) 0.0355(14) 0.0378(14) -0.0053(11) 0.0119(11) -0.0017(11)
C3 0.0468(16) 0.0346(15) 0.0444(15) -0.0069(12) 0.0129(12) -0.0012(12)
C4 0.0470(15) 0.0286(13) 0.0367(13) -0.0040(11) 0.0129(11) -0.0004(11)
C5 0.0495(15) 0.0303(14) 0.0419(14) 0.0014(11) 0.0110(12) 0.0007(11)
C6 0.0503(16) 0.0326(14) 0.0440(15) 0.0034(12) 0.0121(12) 0.0038(12)
C7 0.0558(17) 0.0354(15) 0.0447(15) 0.0020(12) 0.0109(13) 0.0014(12)
C8 0.0579(18) 0.0334(15) 0.0582(18) 0.0011(13) 0.0112(14) 0.0008(13)
C9 0.0580(18) 0.0327(15) 0.0649(19) 0.0126(14) 0.0076(14) 0.0026(13)
C10 0.084(2) 0.0497(19) 0.0428(16) 0.0121(14) 0.0063(15) 0.0010(16)
C11 0.088(2) 0.0353(16) 0.0444(16) -0.0012(13) 0.0109(15) -0.0014(15)
C12 0.0533(16) 0.0267(12) 0.0336(13) 0.0016(10) 0.0134(11) 0.0048(11)
C13 0.0528(18) 0.0395(15) 0.0588(17) -0.0137(13) 0.0137(13) -0.0085(13)
C14 0.0507(17) 0.0525(18) 0.0659(19) -0.0140(15) 0.0192(14) -0.0005(14)
C15 0.0636(19) 0.0329(15) 0.0426(15) -0.0042(11) 0.0186(13) 0.0010(13)
C16 0.0620(19) 0.0367(15) 0.0536(17) -0.0107(13) 0.0180(14) -0.0100(13)
C17 0.0475(16) 0.0404(16) 0.0565(16) -0.0057(13) 0.0149(13) -0.0015(12)
C18 0.089(2) 0.0458(18) 0.078(2) -0.0167(16) 0.0374(18) 0.0000(16)
C19 0.0705(19) 0.0373(15) 0.0326(13) 0.0027(11) 0.0038(13) 0.0042(14)
C20 0.073(2) 0.0430(17) 0.0502(17) 0.0017(13) 0.0078(15) 0.0106(15)
C21 0.096(3) 0.059(2) 0.0562(19) -0.0015(17) 0.0043(18) 0.0288(19)
C22 0.149(4) 0.044(2) 0.053(2) 0.0090(16) 0.000(2) 0.024(2)
C23 0.144(4) 0.050(2) 0.068(2) 0.0227(18) 0.014(2) -0.008(2)
C24 0.095(3) 0.053(2) 0.0561(19) 0.0119(16) 0.0164(17) -0.0070(18)
C25 0.130(3) 0.048(2) 0.057(2) 0.0022(17) 0.025(2) 0.008(2)
C26 0.100(3) 0.069(2) 0.076(2) -0.0245(19) 0.022(2) -0.004(2)
C27 0.138(4) 0.075(3) 0.074(2) 0.019(2) 0.035(2) 0.014(2)
N1 0.0613(14) 0.0394(13) 0.0361(12) 0.0021(10) 0.0097(10) 0.0018(11)
N2 0.0724(16) 0.0487(15) 0.0385(12) 0.0007(11) 0.0151(11) 0.0062(12)
N3 0.0637(15) 0.0470(14) 0.0408(13) -0.0033(11) 0.0139(11) 0.0030(12)
N4 0.0556(13) 0.0312(11) 0.0369(11) 0.0012(9) 0.0126(9) 0.0057(10)
N5 0.0491(12) 0.0272(11) 0.0411(12) -0.0010(9) 0.0143(10) 0.0028(9)
N6 0.0589(14) 0.0335(12) 0.0406(12) 0.0051(10) 0.0156(10) 0.0061(10)
N7 0.0567(14) 0.0275(11) 0.0380(12) 0.0013(9) 0.0150(10) 0.0059(10)
N8 0.0774(16) 0.0294(12) 0.0371(12) 0.0002(9) 0.0147(11) 0.0051(11)
N9 0.0731(17) 0.0495(15) 0.0481(14) 0.0007(12) 0.0171(12) 0.0073(12)
O1 0.0770(14) 0.0392(11) 0.0585(12) -0.0041(9) 0.0236(10) 0.0152(10)
O2 0.208(3) 0.0533(15) 0.0605(15) -0.0151(13) 0.0390(17) 0.0026(17)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.354(3) . ?
C1 N4 1.361(3) . ?
C1 C2 1.386(3) . ?
C2 N3 1.371(3) . ?
C2 C3 1.435(3) . ?
C3 O1 1.211(3) . ?
C3 N5 1.420(3) . ?
C4 N4 1.307(3) . ?
C4 N7 1.368(3) . ?
C4 N5 1.370(3) . ?
C5 N6 1.311(3) . ?
C5 N8 1.347(3) . ?
C5 N7 1.389(3) . ?
C6 C7 1.385(3) . ?
C6 C11 1.391(4) . ?
C6 N8 1.414(3) . ?
C7 C8 1.381(3) . ?
C8 C9 1.378(4) . ?
C9 C10 1.369(4) . ?
C10 C11 1.381(4) . ?
C12 C13 1.370(4) . ?
C12 C17 1.374(3) . ?
C12 N7 1.444(3) . ?
C13 C14 1.390(4) . ?
C14 C15 1.381(4) . ?
C15 C16 1.380(4) . ?
C15 C18 1.507(4) . ?
C16 C17 1.383(4) . ?
C19 C20 1.370(4) . ?
C19 C24 1.373(4) . ?
C19 N1 1.439(3) . ?
C20 C21 1.392(4) . ?
C21 C22 1.367(5) . ?
C22 C23 1.373(5) . ?
C23 C24 1.393(5) . ?
C25 O2 1.216(4) . ?
C25 N9 1.300(4) . ?
C26 N9 1.463(4) . ?
C27 N9 1.441(4) . ?
N1 N2 1.377(3) . ?
N2 N3 1.304(3) . ?
N5 N6 1.403(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
N1 C1 N4 126.5(2) . . ?
N1 C1 C2 104.5(2) . . ?
N4 C1 C2 129.0(2) . . ?
N3 C2 C1 109.1(2) . . ?
N3 C2 C3 129.0(2) . . ?
C1 C2 C3 121.7(2) . . ?
O1 C3 N5 121.8(2) . . ?
O1 C3 C2 130.7(2) . . ?
N5 C3 C2 107.5(2) . . ?
N4 C4 N7 126.7(2) . . ?
N4 C4 N5 128.5(2) . . ?
N7 C4 N5 104.8(2) . . ?
N6 C5 N8 126.9(2) . . ?
N6 C5 N7 112.9(2) . . ?
N8 C5 N7 120.2(2) . . ?
C7 C6 C11 118.9(2) . . ?
C7 C6 N8 123.2(2) . . ?
C11 C6 N8 117.8(2) . . ?
C8 C7 C6 120.2(2) . . ?
C9 C8 C7 120.6(3) . . ?
C10 C9 C8 119.3(3) . . ?
C9 C10 C11 120.8(3) . . ?
C10 C11 C6 120.1(3) . . ?
C13 C12 C17 121.0(2) . . ?
C13 C12 N7 120.1(2) . . ?
C17 C12 N7 118.9(2) . . ?
C12 C13 C14 118.9(2) . . ?
C15 C14 C13 121.6(3) . . ?
C16 C15 C14 117.9(2) . . ?
C16 C15 C18 120.8(3) . . ?
C14 C15 C18 121.3(3) . . ?
C15 C16 C17 121.4(3) . . ?
C12 C17 C16 119.3(3) . . ?
C20 C19 C24 122.1(3) . . ?
C20 C19 N1 119.0(2) . . ?
C24 C19 N1 118.8(3) . . ?
C19 C20 C21 118.6(3) . . ?
C22 C21 C20 120.4(4) . . ?
C21 C22 C23 120.1(3) . . ?
C22 C23 C24 120.7(3) . . ?
C19 C24 C23 118.1(4) . . ?
O2 C25 N9 125.9(3) . . ?
C1 N1 N2 109.8(2) . . ?
C1 N1 C19 129.3(2) . . ?
N2 N1 C19 120.9(2) . . ?
N3 N2 N1 108.3(2) . . ?
N2 N3 C2 108.2(2) . . ?
C4 N4 C1 108.3(2) . . ?
C4 N5 N6 112.23(18) . . ?
C4 N5 C3 124.9(2) . . ?
N6 N5 C3 122.75(19) . . ?
C5 N6 N5 103.03(19) . . ?
C4 N7 C5 107.0(2) . . ?
C4 N7 C12 123.9(2) . . ?
C5 N7 C12 129.0(2) . . ?
C5 N8 C6 126.5(2) . . ?
C25 N9 C27 120.1(3) . . ?
C25 N9 C26 120.7(3) . . ?
C27 N9 C26 119.0(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
N1 C1 C2 N3 0.3(3) . . . . ?
N4 C1 C2 N3 -176.5(2) . . . . ?
N1 C1 C2 C3 176.7(2) . . . . ?
N4 C1 C2 C3 -0.1(4) . . . . ?
N3 C2 C3 O1 -1.0(5) . . . . ?
C1 C2 C3 O1 -176.6(3) . . . . ?
N3 C2 C3 N5 177.8(2) . . . . ?
C1 C2 C3 N5 2.2(3) . . . . ?
C11 C6 C7 C8 1.4(4) . . . . ?
N8 C6 C7 C8 -175.2(2) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C8 C9 C10 C11 1.2(4) . . . . ?
C9 C10 C11 C6 -0.5(5) . . . . ?
C7 C6 C11 C10 -0.8(4) . . . . ?
N8 C6 C11 C10 176.0(3) . . . . ?
C17 C12 C13 C14 0.5(4) . . . . ?
N7 C12 C13 C14 -177.0(2) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
C13 C14 C15 C16 -1.3(4) . . . . ?
C13 C14 C15 C18 176.2(3) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C18 C15 C16 C17 -177.0(3) . . . . ?
C13 C12 C17 C16 -1.4(4) . . . . ?
N7 C12 C17 C16 176.2(2) . . . . ?
C15 C16 C17 C12 0.9(4) . . . . ?
C24 C19 C20 C21 -0.1(4) . . . . ?
N1 C19 C20 C21 -179.3(2) . . . . ?
C19 C20 C21 C22 0.1(5) . . . . ?
C20 C21 C22 C23 -0.3(5) . . . . ?
C21 C22 C23 C24 0.5(6) . . . . ?
C20 C19 C24 C23 0.3(5) . . . . ?
N1 C19 C24 C23 179.5(3) . . . . ?
C22 C23 C24 C19 -0.5(5) . . . . ?
N4 C1 N1 N2 176.7(2) . . . . ?
C2 C1 N1 N2 -0.3(3) . . . . ?
N4 C1 N1 C19 -5.2(4) . . . . ?
C2 C1 N1 C19 177.8(3) . . . . ?
C20 C19 N1 C1 -51.9(4) . . . . ?
C24 C19 N1 C1 128.9(3) . . . . ?
C20 C19 N1 N2 126.0(3) . . . . ?
C24 C19 N1 N2 -53.2(3) . . . . ?
C1 N1 N2 N3 0.1(3) . . . . ?
C19 N1 N2 N3 -178.2(2) . . . . ?
N1 N2 N3 C2 0.1(3) . . . . ?
C1 C2 N3 N2 -0.3(3) . . . . ?
C3 C2 N3 N2 -176.3(2) . . . . ?
N7 C4 N4 C1 179.4(2) . . . . ?
N5 C4 N4 C1 -0.6(3) . . . . ?
N1 C1 N4 C4 -177.1(2) . . . . ?
C2 C1 N4 C4 -0.9(4) . . . . ?
N4 C4 N5 N6 179.5(2) . . . . ?
N7 C4 N5 N6 -0.5(3) . . . . ?
N4 C4 N5 C3 3.1(4) . . . . ?
N7 C4 N5 C3 -176.9(2) . . . . ?
O1 C3 N5 C4 175.4(2) . . . . ?
C2 C3 N5 C4 -3.6(3) . . . . ?
O1 C3 N5 N6 -0.6(4) . . . . ?
C2 C3 N5 N6 -179.5(2) . . . . ?
N8 C5 N6 N5 178.9(2) . . . . ?
N7 C5 N6 N5 -1.3(3) . . . . ?
C4 N5 N6 C5 1.1(3) . . . . ?
C3 N5 N6 C5 177.5(2) . . . . ?
N4 C4 N7 C5 179.8(2) . . . . ?
N5 C4 N7 C5 -0.2(3) . . . . ?
N4 C4 N7 C12 1.7(4) . . . . ?
N5 C4 N7 C12 -178.3(2) . . . . ?
N6 C5 N7 C4 1.0(3) . . . . ?
N8 C5 N7 C4 -179.2(2) . . . . ?
N6 C5 N7 C12 178.9(2) . . . . ?
N8 C5 N7 C12 -1.2(4) . . . . ?
C13 C12 N7 C4 90.6(3) . . . . ?
C17 C12 N7 C4 -87.0(3) . . . . ?
C13 C12 N7 C5 -87.0(3) . . . . ?
C17 C12 N7 C5 95.4(3) . . . . ?
N6 C5 N8 C6 -14.8(4) . . . . ?
N7 C5 N8 C6 165.3(2) . . . . ?
C7 C6 N8 C5 -11.7(4) . . . . ?
C11 C6 N8 C5 171.6(3) . . . . ?
O2 C25 N9 C27 0.7(6) . . . . ?
O2 C25 N9 C26 176.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.041