# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2001

data_nuc7

_database_code_CSD	161624

_journal_coden_Cambridge      207
_publ_requested_journal       'Perkin Transactions 1'

loop_
_publ_author_name
'Boyle, F. T.'
'Clegg, William'
'Curtin, Nicola J.'
'Edwards, Andrew J.'
'Golding, B.'
'Griffin, R.'
'Northen, Julian S.'

_publ_contact_author_name     	'Prof B Golding'  
_publ_contact_author_address 
;
Prof B Golding
Department of Chemistry
Bedson Building
University of Newcastle
Newcastle upon Tyne
NE1 7RU
UK
;         
_publ_contact_author_email       'B.T.GOLDING@NEWCASTLE.AC.UK'

_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_sum
'C16 H19 N7 O'
_chemical_formula_weight          325.38

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            orthorhombic
_symmetry_space_group_name_H-M    Pbcn

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

_cell_length_a                    38.754(8)
_cell_length_b                    7.9580(16)
_cell_length_c                    20.954(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      6462(2)
_cell_formula_units_Z             16
_cell_measurement_temperature     160(2)
_cell_measurement_reflns_used     63
_cell_measurement_theta_min       2.0
_cell_measurement_theta_max       27.0

_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.338
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              2752
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?

_exptl_special_details
;
?
;

_diffrn_ambient_temperature       160(2)
_diffrn_radiation_wavelength      0.6889
_diffrn_radiation_type            synchrotron
_diffrn_radiation_source          'Daresbury SRS station 9.8'
_diffrn_radiation_monochromator   'silicon 111'
_diffrn_measurement_device_type   'Siemens SMART CCD diffractometer'
_diffrn_measurement_method        '\w rotation with narrow frames'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          0
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         15
_diffrn_reflns_number             15409
_diffrn_reflns_av_R_equivalents   0.0678
_diffrn_reflns_av_sigmaI/netI     0.0966
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        51
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        25
_diffrn_reflns_theta_min          1.95
_diffrn_reflns_theta_max          27.03
_reflns_number_total              6638
_reflns_number_gt                 3737
_reflns_threshold_expression      >2sigma(I)

_computing_data_collection        'Siemens SMART'
_computing_cell_refinement        'Siemens SMART'
_computing_data_reduction         'Siemens SAINT'
_computing_structure_solution     'Siemens SHELXTL'
_computing_structure_refinement   'Siemens SHELXTL'
_computing_molecular_graphics     'Siemens SHELXTL'
_computing_publication_material   'SHELXTL and local programs'

_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 w=1/[\s^2^(Fo^2^)+(0.0666P)^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      SHELXL
_refine_ls_extinction_coef        0.0027(3)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns          6638
_refine_ls_number_parameters      460
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1088
_refine_ls_R_factor_gt            0.0558
_refine_ls_wR_factor_ref          0.1386
_refine_ls_wR_factor_gt           0.1206
_refine_ls_goodness_of_fit_ref    0.893
_refine_ls_restrained_S_all       0.893
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.16270(5) 0.8044(2) 0.03999(9) 0.0356(5) Uani 1 d . . .
H1 H 0.1809(7) 0.777(4) 0.0145(13) 0.043 Uiso 1 d . . .
N1 N 0.15017(5) 0.5887(3) 0.15090(10) 0.0253(5) Uani 1 d . . .
H1N H 0.1716(6) 0.605(3) 0.1680(12) 0.030 Uiso 1 d . . .
N2 N 0.13018(5) 0.7078(2) 0.24356(10) 0.0210(5) Uani 1 d . . .
N3 N 0.13670(5) 0.8665(3) 0.36173(10) 0.0276(5) Uani 1 d . . .
H3N H 0.1557(7) 0.858(3) 0.3318(13) 0.033 Uiso 1 d . . .
N4 N 0.07796(5) 0.8453(3) 0.37893(10) 0.0285(5) Uani 1 d . . .
N5 N 0.03958(5) 0.7362(3) 0.29882(10) 0.0267(5) Uani 1 d . . .
N6 N 0.09138(5) 0.6026(3) 0.16213(10) 0.0227(5) Uani 1 d . . .
N7 N 0.03259(5) 0.6100(3) 0.17365(10) 0.0260(5) Uani 1 d . . .
H7N H 0.0155(7) 0.643(3) 0.1950(12) 0.031 Uiso 1 d . . .
C1 C 0.13772(6) 0.6723(3) 0.03914(13) 0.0319(7) Uani 1 d . . .
H1A H 0.1361 0.6262 -0.0047 0.038 Uiso 1 calc R . .
H1B H 0.1149 0.7190 0.0506 0.038 Uiso 1 calc R . .
C2 C 0.14649(6) 0.5315(3) 0.08478(12) 0.0264(6) Uani 1 d . . .
H2A H 0.1281 0.4452 0.0828 0.032 Uiso 1 calc R . .
H2B H 0.1683 0.4782 0.0710 0.032 Uiso 1 calc R . .
C3 C 0.12311(6) 0.6356(3) 0.18712(12) 0.0204(5) Uani 1 d . . .
C4 C 0.10156(6) 0.7428(3) 0.27961(12) 0.0216(6) Uani 1 d . . .
C5 C 0.10533(6) 0.8192(3) 0.34161(12) 0.0231(6) Uani 1 d . . .
C6 C 0.14217(7) 0.9506(4) 0.42268(14) 0.0417(8) Uani 1 d . . .
H6A H 0.1276 1.0511 0.4249 0.063 Uiso 1 calc R . .
H6B H 0.1665 0.9832 0.4265 0.063 Uiso 1 calc R . .
H6C H 0.1361 0.8741 0.4576 0.063 Uiso 1 calc R . .
C7 C 0.04694(6) 0.8013(3) 0.35521(13) 0.0287(6) Uani 1 d . . .
H7A H 0.0278 0.8196 0.3827 0.034 Uiso 1 calc R . .
C8 C 0.06794(6) 0.7093(3) 0.26073(12) 0.0211(6) Uani 1 d . . .
C9 C 0.06394(6) 0.6397(3) 0.19769(12) 0.0213(6) Uani 1 d . . .
C10 C 0.02804(6) 0.5155(3) 0.11479(12) 0.0276(6) Uani 1 d . . .
H10A H 0.0034 0.4837 0.1111 0.033 Uiso 1 calc R . .
H10B H 0.0416 0.4104 0.1180 0.033 Uiso 1 calc R . .
C11 C 0.03852(6) 0.6056(3) 0.05430(12) 0.0252(6) Uani 1 d . . .
C12 C 0.03696(6) 0.7790(3) 0.04880(13) 0.0298(6) Uani 1 d . . .
H12 H 0.0296 0.8440 0.0843 0.036 Uiso 1 calc R . .
C13 C 0.04594(7) 0.8601(4) -0.00793(14) 0.0355(7) Uani 1 d . . .
H13 H 0.0445 0.9790 -0.0111 0.043 Uiso 1 calc R . .
C14 C 0.05702(7) 0.7650(4) -0.05964(14) 0.0358(7) Uani 1 d . . .
H14 H 0.0633 0.8186 -0.0984 0.043 Uiso 1 calc R . .
C15 C 0.05885(7) 0.5918(4) -0.05439(14) 0.0368(7) Uani 1 d . . .
H15 H 0.0664 0.5269 -0.0897 0.044 Uiso 1 calc R . .
C16 C 0.04972(6) 0.5124(4) 0.00186(13) 0.0314(6) Uani 1 d . . .
H16 H 0.0511 0.3934 0.0048 0.038 Uiso 1 calc R . .
O2 O 0.27880(5) 1.2446(3) -0.02818(10) 0.0515(7) Uani 1 d . . .
H2 H 0.2757(9) 1.210(4) -0.0605(16) 0.062 Uiso 1 d . . .
N8 N 0.26910(5) 1.2672(2) 0.10971(10) 0.0208(5) Uani 1 d . . .
H8N H 0.2920(6) 1.279(3) 0.1122(12) 0.025 Uiso 1 d . . .
N9 N 0.27578(5) 1.1177(2) 0.20215(9) 0.0183(4) Uani 1 d . . .
N10 N 0.31330(5) 0.9966(3) 0.30798(10) 0.0236(5) Uani 1 d . . .
H10N H 0.3224(6) 1.068(3) 0.2816(12) 0.028 Uiso 1 d . . .
N11 N 0.26336(5) 0.8888(2) 0.35185(10) 0.0215(5) Uani 1 d . . .
N12 N 0.20806(5) 0.9211(2) 0.30169(10) 0.0220(5) Uani 1 d . . .
N13 N 0.21939(5) 1.1618(2) 0.15456(9) 0.0185(5) Uani 1 d . . .
N14 N 0.17126(5) 1.0287(3) 0.19641(11) 0.0259(5) Uani 1 d . . .
H14N H 0.1629(6) 0.954(3) 0.2224(12) 0.031 Uiso 1 d . . .
C17 C 0.24627(7) 1.2905(4) -0.00146(13) 0.0338(7) Uani 1 d . . .
H17A H 0.2314 1.1895 0.0019 0.041 Uiso 1 calc R . .
H17B H 0.2346 1.3719 -0.0300 0.041 Uiso 1 calc R . .
C18 C 0.25074(7) 1.3663(3) 0.06260(12) 0.0280(6) Uani 1 d . . .
H18A H 0.2631 1.4743 0.0574 0.034 Uiso 1 calc R . .
H18B H 0.2276 1.3924 0.0799 0.034 Uiso 1 calc R . .
C19 C 0.25415(6) 1.1803(3) 0.15794(11) 0.0170(5) Uani 1 d . . .
C20 C 0.25971(6) 1.0333(3) 0.25059(12) 0.0188(5) Uani 1 d . . .
C21 C 0.27927(6) 0.9715(3) 0.30463(12) 0.0194(5) Uani 1 d . . .
C22 C 0.33362(6) 0.9450(4) 0.36320(13) 0.0310(7) Uani 1 d . . .
H22A H 0.3252 1.0036 0.4013 0.046 Uiso 1 calc R . .
H22B H 0.3579 0.9733 0.3561 0.046 Uiso 1 calc R . .
H22C H 0.3314 0.8234 0.3693 0.046 Uiso 1 calc R . .
C23 C 0.22874(6) 0.8695(3) 0.34728(12) 0.0238(6) Uani 1 d . . .
H23 H 0.2180 0.8110 0.3815 0.029 Uiso 1 calc R . .
C24 C 0.22466(6) 1.0040(3) 0.25281(12) 0.0185(5) Uani 1 d . . .
C25 C 0.20468(6) 1.0675(3) 0.19957(12) 0.0197(5) Uani 1 d . . .
C26 C 0.14660(6) 1.0962(3) 0.15012(12) 0.0276(6) Uani 1 d . . .
H26A H 0.1427 1.0133 0.1157 0.033 Uiso 1 calc R . .
H26B H 0.1560 1.2001 0.1307 0.033 Uiso 1 calc R . .
C27 C 0.11284(6) 1.1344(3) 0.18380(12) 0.0244(6) Uani 1 d . . .
C28 C 0.08183(6) 1.0698(3) 0.16206(14) 0.0334(7) Uani 1 d . . .
H28 H 0.0814 1.0020 0.1248 0.040 Uiso 1 calc R . .
C29 C 0.05136(7) 1.1037(4) 0.19453(16) 0.0450(8) Uani 1 d . . .
H29 H 0.0302 1.0585 0.1795 0.054 Uiso 1 calc R . .
C30 C 0.05178(8) 1.2026(4) 0.24839(16) 0.0441(8) Uani 1 d . . .
H30 H 0.0309 1.2255 0.2706 0.053 Uiso 1 calc R . .
C31 C 0.08234(7) 1.2679(4) 0.26989(14) 0.0387(7) Uani 1 d . . .
H31 H 0.0826 1.3370 0.3069 0.046 Uiso 1 calc R . .
C32 C 0.11275(7) 1.2340(3) 0.23814(14) 0.0338(7) Uani 1 d . . .
H32 H 0.1338 1.2793 0.2536 0.041 Uiso 1 calc R . .

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
O1 0.0306(10) 0.0452(12) 0.0309(12) 0.0057(10) 0.0055(9) 0.0035(9)
N1 0.0156(10) 0.0424(13) 0.0180(13) -0.0004(11) 0.0001(9) 0.0044(9)
N2 0.0159(10) 0.0295(11) 0.0175(12) -0.0003(10) 0.0003(8) 0.0004(8)
N3 0.0197(11) 0.0416(13) 0.0214(13) -0.0095(11) 0.0037(9) -0.0049(9)
N4 0.0214(11) 0.0384(13) 0.0255(13) -0.0041(11) 0.0032(9) -0.0033(9)
N5 0.0191(10) 0.0361(13) 0.0249(13) -0.0021(11) 0.0019(9) -0.0002(9)
N6 0.0196(10) 0.0304(12) 0.0183(12) 0.0018(10) -0.0029(9) 0.0013(8)
N7 0.0172(10) 0.0401(13) 0.0208(13) -0.0046(11) -0.0011(9) 0.0004(9)
C1 0.0227(13) 0.0504(18) 0.0227(16) -0.0005(14) -0.0008(11) 0.0039(12)
C2 0.0226(13) 0.0377(16) 0.0189(15) -0.0038(12) 0.0003(11) 0.0036(11)
C3 0.0182(12) 0.0244(13) 0.0186(15) 0.0056(11) 0.0011(10) 0.0016(10)
C4 0.0202(12) 0.0251(13) 0.0194(15) 0.0035(11) -0.0009(10) -0.0011(10)
C5 0.0242(13) 0.0245(13) 0.0206(15) 0.0020(12) 0.0001(11) 0.0008(10)
C6 0.0330(15) 0.060(2) 0.0317(19) -0.0173(16) -0.0021(13) -0.0095(14)
C7 0.0208(13) 0.0397(16) 0.0255(16) -0.0049(13) 0.0066(11) -0.0008(11)
C8 0.0186(12) 0.0244(13) 0.0202(15) 0.0010(11) 0.0002(10) 0.0019(9)
C9 0.0185(12) 0.0243(13) 0.0212(15) 0.0025(12) 0.0013(10) 0.0011(10)
C10 0.0235(13) 0.0350(15) 0.0242(16) -0.0014(13) -0.0022(11) -0.0055(11)
C11 0.0162(11) 0.0350(15) 0.0243(15) -0.0026(13) -0.0049(11) -0.0033(10)
C12 0.0248(13) 0.0351(16) 0.0293(17) -0.0031(13) -0.0006(11) -0.0021(11)
C13 0.0351(15) 0.0354(16) 0.0359(19) 0.0063(15) -0.0034(13) -0.0018(12)
C14 0.0404(16) 0.0453(18) 0.0218(16) 0.0044(15) -0.0006(13) -0.0092(13)
C15 0.0382(16) 0.0464(18) 0.0258(18) -0.0085(15) -0.0008(13) -0.0076(13)
C16 0.0340(15) 0.0322(15) 0.0280(17) -0.0033(14) -0.0031(13) -0.0045(12)
O2 0.0281(11) 0.103(2) 0.0233(13) -0.0239(13) -0.0055(10) 0.0047(11)
N8 0.0227(11) 0.0241(11) 0.0156(12) 0.0029(9) -0.0006(9) -0.0026(9)
N9 0.0202(10) 0.0214(10) 0.0134(12) 0.0005(9) -0.0003(8) -0.0016(8)
N10 0.0192(10) 0.0319(12) 0.0197(13) 0.0082(10) -0.0014(9) -0.0024(9)
N11 0.0229(11) 0.0276(11) 0.0141(12) 0.0027(10) 0.0010(8) -0.0025(8)
N12 0.0226(10) 0.0268(11) 0.0166(12) 0.0019(10) 0.0008(9) -0.0035(9)
N13 0.0230(10) 0.0209(11) 0.0117(11) 0.0003(9) 0.0000(8) 0.0000(8)
N14 0.0194(11) 0.0338(13) 0.0246(14) 0.0105(11) -0.0029(9) -0.0030(9)
C17 0.0387(16) 0.0365(16) 0.0261(17) -0.0004(13) -0.0039(13) 0.0097(13)
C18 0.0361(14) 0.0273(14) 0.0206(15) 0.0053(12) 0.0012(12) 0.0075(11)
C19 0.0234(12) 0.0159(11) 0.0116(13) -0.0021(10) 0.0024(10) -0.0004(9)
C20 0.0218(12) 0.0175(12) 0.0171(14) -0.0030(11) 0.0021(10) 0.0008(9)
C21 0.0235(12) 0.0201(12) 0.0145(14) -0.0024(11) 0.0005(10) 0.0017(10)
C22 0.0208(13) 0.0445(17) 0.0276(17) 0.0086(14) -0.0037(11) -0.0003(11)
C23 0.0247(13) 0.0311(14) 0.0155(15) 0.0038(12) 0.0015(11) -0.0033(10)
C24 0.0218(12) 0.0206(12) 0.0130(14) -0.0026(11) -0.0002(10) -0.0010(9)
C25 0.0207(12) 0.0182(12) 0.0202(15) -0.0026(11) 0.0028(10) -0.0001(10)
C26 0.0232(13) 0.0361(15) 0.0236(16) 0.0072(13) -0.0046(11) 0.0016(11)
C27 0.0269(13) 0.0245(14) 0.0219(16) 0.0044(12) -0.0031(11) 0.0009(10)
C28 0.0270(14) 0.0338(15) 0.0394(18) -0.0022(14) -0.0051(13) 0.0013(11)
C29 0.0221(14) 0.0479(19) 0.065(2) -0.0001(18) 0.0002(15) -0.0020(13)
C30 0.0380(17) 0.0476(19) 0.047(2) 0.0099(17) 0.0160(15) 0.0115(14)
C31 0.0456(18) 0.0421(17) 0.0286(18) -0.0010(15) 0.0058(14) 0.0042(14)
C32 0.0333(15) 0.0342(15) 0.0339(18) -0.0013(14) -0.0030(13) -0.0046(12)

_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
O1 C1 1.430(3) . ?
N1 C3 1.347(3) . ?
N1 C2 1.465(3) . ?
N2 C3 1.343(3) . ?
N2 C4 1.371(3) . ?
N3 C5 1.341(3) . ?
N3 C6 1.458(3) . ?
N4 C5 1.334(3) . ?
N4 C7 1.347(3) . ?
N5 C7 1.321(3) . ?
N5 C8 1.375(3) . ?
N6 C9 1.332(3) . ?
N6 C3 1.362(3) . ?
N7 C9 1.336(3) . ?
N7 C10 1.455(3) . ?
C1 C2 1.512(3) . ?
C4 C8 1.387(3) . ?
C4 C5 1.442(3) . ?
C8 C9 1.441(3) . ?
C10 C11 1.512(4) . ?
C11 C12 1.386(4) . ?
C11 C16 1.395(4) . ?
C12 C13 1.397(4) . ?
C13 C14 1.390(4) . ?
C14 C15 1.384(4) . ?
C15 C16 1.383(4) . ?
O2 C17 1.427(3) . ?
N8 C19 1.355(3) . ?
N8 C18 1.450(3) . ?
N9 C19 1.345(3) . ?
N9 C20 1.367(3) . ?
N10 C21 1.336(3) . ?
N10 C22 1.459(3) . ?
N11 C21 1.339(3) . ?
N11 C23 1.354(3) . ?
N12 C23 1.313(3) . ?
N12 C24 1.378(3) . ?
N13 C25 1.333(3) . ?
N13 C19 1.357(3) . ?
N14 C25 1.333(3) . ?
N14 C26 1.464(3) . ?
C17 C18 1.482(4) . ?
C20 C24 1.379(3) . ?
C20 C21 1.449(3) . ?
C24 C25 1.449(3) . ?
C26 C27 1.517(3) . ?
C27 C28 1.384(3) . ?
C27 C32 1.388(4) . ?
C28 C29 1.389(4) . ?
C29 C30 1.376(4) . ?
C30 C31 1.369(4) . ?
C31 C32 1.380(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C2 122.9(2) . . ?
C3 N2 C4 114.02(19) . . ?
C5 N3 C6 122.4(2) . . ?
C5 N4 C7 116.9(2) . . ?
C7 N5 C8 114.0(2) . . ?
C9 N6 C3 117.6(2) . . ?
C9 N7 C10 121.4(2) . . ?
O1 C1 C2 112.6(2) . . ?
N1 C2 C1 112.9(2) . . ?
N2 C3 N1 117.1(2) . . ?
N2 C3 N6 127.2(2) . . ?
N1 C3 N6 115.6(2) . . ?
N2 C4 C8 124.3(2) . . ?
N2 C4 C5 120.0(2) . . ?
C8 C4 C5 115.7(2) . . ?
N4 C5 N3 119.5(2) . . ?
N4 C5 C4 120.9(2) . . ?
N3 C5 C4 119.6(2) . . ?
N5 C7 N4 128.7(2) . . ?
N5 C8 C4 123.7(2) . . ?
N5 C8 C9 120.4(2) . . ?
C4 C8 C9 115.9(2) . . ?
N6 C9 N7 118.4(2) . . ?
N6 C9 C8 120.8(2) . . ?
N7 C9 C8 120.8(2) . . ?
N7 C10 C11 115.7(2) . . ?
C12 C11 C16 118.5(3) . . ?
C12 C11 C10 122.0(2) . . ?
C16 C11 C10 119.5(2) . . ?
C11 C12 C13 121.3(3) . . ?
C14 C13 C12 119.3(3) . . ?
C15 C14 C13 119.7(3) . . ?
C14 C15 C16 120.6(3) . . ?
C15 C16 C11 120.5(3) . . ?
C19 N8 C18 125.1(2) . . ?
C19 N9 C20 114.16(19) . . ?
C21 N10 C22 122.2(2) . . ?
C21 N11 C23 117.4(2) . . ?
C23 N12 C24 113.93(19) . . ?
C25 N13 C19 116.65(19) . . ?
C25 N14 C26 125.6(2) . . ?
O2 C17 C18 110.9(2) . . ?
N8 C18 C17 116.9(2) . . ?
N9 C19 N8 115.9(2) . . ?
N9 C19 N13 127.9(2) . . ?
N8 C19 N13 116.2(2) . . ?
N9 C20 C24 123.8(2) . . ?
N9 C20 C21 120.58(19) . . ?
C24 C20 C21 115.6(2) . . ?
N10 C21 N11 119.3(2) . . ?
N10 C21 C20 120.5(2) . . ?
N11 C21 C20 120.2(2) . . ?
N12 C23 N11 128.4(2) . . ?
N12 C24 C20 124.5(2) . . ?
N12 C24 C25 119.33(19) . . ?
C20 C24 C25 116.2(2) . . ?
N13 C25 N14 120.7(2) . . ?
N13 C25 C24 120.8(2) . . ?
N14 C25 C24 118.5(2) . . ?
N14 C26 C27 109.2(2) . . ?
C28 C27 C32 118.7(2) . . ?
C28 C27 C26 121.4(2) . . ?
C32 C27 C26 119.9(2) . . ?
C27 C28 C29 120.3(3) . . ?
C30 C29 C28 120.2(3) . . ?
C31 C30 C29 119.8(3) . . ?
C30 C31 C32 120.4(3) . . ?
C31 C32 C27 120.6(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
C3 N1 C2 C1 72.3(3) . . . . ?
O1 C1 C2 N1 57.5(3) . . . . ?
C4 N2 C3 N1 -176.2(2) . . . . ?
C4 N2 C3 N6 3.3(3) . . . . ?
C2 N1 C3 N2 -170.8(2) . . . . ?
C2 N1 C3 N6 9.6(3) . . . . ?
C9 N6 C3 N2 -2.6(4) . . . . ?
C9 N6 C3 N1 176.9(2) . . . . ?
C3 N2 C4 C8 -0.4(3) . . . . ?
C3 N2 C4 C5 179.5(2) . . . . ?
C7 N4 C5 N3 177.5(2) . . . . ?
C7 N4 C5 C4 -1.8(4) . . . . ?
C6 N3 C5 N4 -1.8(4) . . . . ?
C6 N3 C5 C4 177.4(2) . . . . ?
N2 C4 C5 N4 -176.1(2) . . . . ?
C8 C4 C5 N4 3.8(4) . . . . ?
N2 C4 C5 N3 4.7(4) . . . . ?
C8 C4 C5 N3 -175.4(2) . . . . ?
C8 N5 C7 N4 0.9(4) . . . . ?
C5 N4 C7 N5 -0.7(4) . . . . ?
C7 N5 C8 C4 1.6(4) . . . . ?
C7 N5 C8 C9 -179.6(2) . . . . ?
N2 C4 C8 N5 176.1(2) . . . . ?
C5 C4 C8 N5 -3.7(4) . . . . ?
N2 C4 C8 C9 -2.7(4) . . . . ?
C5 C4 C8 C9 177.4(2) . . . . ?
C3 N6 C9 N7 179.2(2) . . . . ?
C3 N6 C9 C8 -1.1(3) . . . . ?
C10 N7 C9 N6 9.7(4) . . . . ?
C10 N7 C9 C8 -170.0(2) . . . . ?
N5 C8 C9 N6 -175.4(2) . . . . ?
C4 C8 C9 N6 3.5(3) . . . . ?
N5 C8 C9 N7 4.2(4) . . . . ?
C4 C8 C9 N7 -176.9(2) . . . . ?
C9 N7 C10 C11 -72.0(3) . . . . ?
N7 C10 C11 C12 -29.0(3) . . . . ?
N7 C10 C11 C16 151.8(2) . . . . ?
C16 C11 C12 C13 0.7(4) . . . . ?
C10 C11 C12 C13 -178.4(2) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C15 C16 C11 0.0(4) . . . . ?
C12 C11 C16 C15 -0.4(4) . . . . ?
C10 C11 C16 C15 178.8(2) . . . . ?
C19 N8 C18 C17 -102.5(3) . . . . ?
O2 C17 C18 N8 -55.9(3) . . . . ?
C20 N9 C19 N8 178.95(19) . . . . ?
C20 N9 C19 N13 -3.7(3) . . . . ?
C18 N8 C19 N9 -170.2(2) . . . . ?
C18 N8 C19 N13 12.1(3) . . . . ?
C25 N13 C19 N9 -1.5(3) . . . . ?
C25 N13 C19 N8 175.9(2) . . . . ?
C19 N9 C20 C24 4.0(3) . . . . ?
C19 N9 C20 C21 -174.6(2) . . . . ?
C22 N10 C21 N11 -3.5(4) . . . . ?
C22 N10 C21 C20 176.4(2) . . . . ?
C23 N11 C21 N10 178.5(2) . . . . ?
C23 N11 C21 C20 -1.4(3) . . . . ?
N9 C20 C21 N10 0.2(3) . . . . ?
C24 C20 C21 N10 -178.4(2) . . . . ?
N9 C20 C21 N11 -179.9(2) . . . . ?
C24 C20 C21 N11 1.4(3) . . . . ?
C24 N12 C23 N11 0.5(4) . . . . ?
C21 N11 C23 N12 0.4(4) . . . . ?
C23 N12 C24 C20 -0.4(3) . . . . ?
C23 N12 C24 C25 -179.9(2) . . . . ?
N9 C20 C24 N12 -179.1(2) . . . . ?
C21 C20 C24 N12 -0.5(3) . . . . ?
N9 C20 C24 C25 0.4(3) . . . . ?
C21 C20 C24 C25 179.04(19) . . . . ?
C19 N13 C25 N14 -173.3(2) . . . . ?
C19 N13 C25 C24 6.4(3) . . . . ?
C26 N14 C25 N13 -7.3(4) . . . . ?
C26 N14 C25 C24 173.1(2) . . . . ?
N12 C24 C25 N13 173.6(2) . . . . ?
C20 C24 C25 N13 -5.9(3) . . . . ?
N12 C24 C25 N14 -6.7(3) . . . . ?
C20 C24 C25 N14 173.7(2) . . . . ?
C25 N14 C26 C27 -138.7(2) . . . . ?
N14 C26 C27 C28 -126.3(3) . . . . ?
N14 C26 C27 C32 52.7(3) . . . . ?
C32 C27 C28 C29 -0.4(4) . . . . ?
C26 C27 C28 C29 178.6(3) . . . . ?
C27 C28 C29 C30 0.4(4) . . . . ?
C28 C29 C30 C31 0.1(5) . . . . ?
C29 C30 C31 C32 -0.5(5) . . . . ?
C30 C31 C32 C27 0.5(4) . . . . ?
C28 C27 C32 C31 0.0(4) . . . . ?
C26 C27 C32 C31 -179.0(2) . . . . ?

_diffrn_measured_fraction_theta_max    0.768
_diffrn_reflns_theta_full              27.03
_diffrn_measured_fraction_theta_full   0.768
_refine_diff_density_max    0.710
_refine_diff_density_min   -0.261
_refine_diff_density_rms    0.071