# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?

loop_
_publ_author_name
'Sergey Kurbatov'
'Vladimir Minkin'
'Artem Tatarov'
'Regis Goumont'
'Francois Terrier'

_publ_contact_author_name        'Francois Terrier'
_publ_contact_author_address     
;
Department of Chemistry
University of Versailles
45 avenue des Etats Unis
Batiment Lavoisier
Niveau -1
Versailles cedex
78035
FRANCE
;

_publ_contact_author_email       TERRIER@CHIMIE.UVSQ.FR

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Ring Opening and Ring Closure in an Indolizine Structure Activated
through SNAr Coupling with Superelectrophilic 4,6-Dinitrobenzofuroxan.
An Unusual Intramolecular Oxygen Transfer from a N-Oxide Functionality.
;

_publ_section_references         
;
North et al.(1968). North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968).
Acta Cryst. A24, 351--359.

Sheldrick G.M. (1998). SHELXTL v. 5.10, Structure Determination Software
Suite, Bruker AXS, Madison, Wisconsin, USA.

Harms, K. (1996). XCAD4: Program for the LP-correction of CAD4/Mach 3
Diffractometer Data, University of Marburg, Germany

Enraf-Nonius, 1984. Enraf Nonius Delft, Scientific Instrumenta Division,
Netherlands, 1984
;

data_cubas
_database_code_depnum_ccdc_archive 'CCDC 607710'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H10 Br N5 O6'
_chemical_formula_sum            'C20 H10 Br N5 O6'
_chemical_formula_weight         496.24

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'
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'
Br Br -0.2901 2.4595 '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'

_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                   7.1510(14)
_cell_length_b                   19.421(4)
_cell_length_c                   14.006(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.22(3)
_cell_angle_gamma                90.00
_cell_volume                     1901.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      11
_cell_measurement_theta_max      12

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    2.215
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.5562
_exptl_absorpt_correction_T_max  0.8088
_exptl_absorpt_process_details   'North et al. (1968)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       '\q/5/3\q scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 98
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        3
_diffrn_reflns_number            4561
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0775
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         26.96
_reflns_number_total             4104
_reflns_number_gt                2291
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'CAD4 Enraf-Nonius (Enraf-Nonius, 1984)'
_computing_cell_refinement       'CAD4 Enraf-Nonius (Enraf-Nonius, 1984)'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1998)'
_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^)+(0.0607P)^2^+0.4250P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4104
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1274
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
Br1 Br -0.39244(7) 0.12457(3) 0.62155(4) 0.0619(2) Uani 1 1 d . . .
O1 O 0.0938(5) 0.05974(15) 0.2837(2) 0.0628(9) Uani 1 1 d . . .
O2 O 0.0615(4) 0.19173(16) 0.1255(2) 0.0533(8) Uani 1 1 d . . .
O3 O 0.0192(5) 0.13832(17) -0.0130(2) 0.0621(9) Uani 1 1 d . . .
O4 O 0.3130(6) -0.0764(2) -0.0321(3) 0.0902(14) Uani 1 1 d . . .
O5 O 0.5124(8) -0.11910(19) 0.0910(4) 0.1070(16) Uani 1 1 d . . .
O6 O 0.7062(4) 0.00071(15) 0.3411(2) 0.0624(9) Uani 1 1 d . . .
N1 N 0.4406(4) 0.18182(14) 0.2252(2) 0.0302(7) Uani 1 1 d . . .
N2 N 0.0978(5) 0.14399(18) 0.0739(3) 0.0430(8) Uani 1 1 d . . .
N3 N 0.4049(7) -0.0735(2) 0.0532(4) 0.0701(13) Uani 1 1 d . . .
N4 N 0.6472(6) -0.03794(18) 0.2561(3) 0.0605(11) Uani 1 1 d . . .
N5 N 0.5991(5) 0.05989(18) 0.3382(3) 0.0543(10) Uani 1 1 d . . .
C1 C 0.2806(5) 0.22455(18) 0.3505(3) 0.0334(8) Uani 1 1 d . . .
H1A H 0.2668 0.2612 0.3913 0.040 Uiso 1 1 calc R . .
C2 C 0.1795(5) 0.16748(18) 0.3575(3) 0.0321(8) Uani 1 1 d . . .
C3 C 0.1900(6) 0.11045(18) 0.2892(3) 0.0353(9) Uani 1 1 d . . .
C5 C 0.5693(5) 0.18868(19) 0.1681(3) 0.0347(9) Uani 1 1 d . . .
H5A H 0.5896 0.1520 0.1288 0.042 Uiso 1 1 calc R . .
C6 C 0.6703(5) 0.24782(19) 0.1665(3) 0.0377(9) Uani 1 1 d . . .
H6A H 0.7580 0.2517 0.1264 0.045 Uiso 1 1 calc R . .
C7 C 0.6408(5) 0.30173(19) 0.2251(3) 0.0366(9) Uani 1 1 d . . .
H7A H 0.7092 0.3425 0.2257 0.044 Uiso 1 1 calc R . .
C8 C 0.5088(6) 0.29452(19) 0.2828(3) 0.0380(9) Uani 1 1 d . . .
H8A H 0.4857 0.3313 0.3213 0.046 Uiso 1 1 calc R . .
C9 C 0.4099(5) 0.23381(18) 0.2847(2) 0.0295(8) Uani 1 1 d . . .
C1' C 0.0499(5) 0.15903(18) 0.4262(3) 0.0311(8) Uani 1 1 d . . .
C2' C -0.0863(5) 0.20921(18) 0.4316(3) 0.0349(9) Uani 1 1 d . . .
H2'A H -0.0893 0.2496 0.3955 0.042 Uiso 1 1 calc R . .
C3' C -0.2174(5) 0.19941(19) 0.4902(3) 0.0379(9) Uani 1 1 d . . .
H3'A H -0.3111 0.2323 0.4922 0.045 Uiso 1 1 calc R . .
C4' C -0.2075(5) 0.14049(19) 0.5456(3) 0.0356(9) Uani 1 1 d . . .
C5' C -0.0680(5) 0.09206(19) 0.5449(3) 0.0377(9) Uani 1 1 d . . .
H5'A H -0.0594 0.0534 0.5849 0.045 Uiso 1 1 calc R . .
C6' C 0.0592(5) 0.10108(18) 0.4846(3) 0.0339(9) Uani 1 1 d . . .
H6'A H 0.1523 0.0679 0.4830 0.041 Uiso 1 1 calc R . .
C4" C 0.3899(6) -0.01355(19) 0.1085(3) 0.0445(11) Uani 1 1 d . . .
C5" C 0.2635(6) 0.0376(2) 0.0697(3) 0.0424(10) Uani 1 1 d . . .
H5"A H 0.1909 0.0312 0.0069 0.051 Uiso 1 1 calc R . .
C6" C 0.2377(5) 0.09694(19) 0.1173(3) 0.0340(9) Uani 1 1 d . . .
C7" C 0.3353(5) 0.11344(16) 0.2209(3) 0.0305(8) Uani 1 1 d . . .
C8" C 0.4799(5) 0.05804(18) 0.2540(3) 0.0345(9) Uani 1 1 d . . .
C9" C 0.5072(6) -0.00220(19) 0.2031(3) 0.0419(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
Br1 0.0524(3) 0.0681(3) 0.0767(4) 0.0008(3) 0.0392(3) -0.0087(3)
O1 0.081(2) 0.0484(18) 0.074(2) -0.0250(16) 0.0507(18) -0.0343(18)
O2 0.0421(18) 0.0483(18) 0.069(2) 0.0021(16) 0.0109(16) 0.0121(14)
O3 0.0536(19) 0.092(3) 0.0354(18) 0.0177(16) -0.0021(15) -0.0054(18)
O4 0.099(3) 0.090(3) 0.099(3) -0.062(3) 0.060(3) -0.052(2)
O5 0.141(4) 0.037(2) 0.161(4) -0.022(2) 0.073(4) 0.013(2)
O6 0.053(2) 0.0476(19) 0.080(2) 0.0181(18) -0.0018(17) 0.0089(16)
N1 0.0326(17) 0.0256(16) 0.0342(17) -0.0031(13) 0.0109(14) -0.0027(13)
N2 0.0365(19) 0.050(2) 0.044(2) 0.0065(18) 0.0114(17) -0.0061(17)
N3 0.086(3) 0.040(2) 0.104(4) -0.031(3) 0.064(3) -0.019(2)
N4 0.058(3) 0.037(2) 0.092(3) 0.011(2) 0.027(2) 0.0075(19)
N5 0.047(2) 0.044(2) 0.065(3) 0.0144(19) -0.004(2) 0.0093(18)
C1 0.039(2) 0.0274(19) 0.035(2) -0.0023(16) 0.0118(17) 0.0002(17)
C2 0.036(2) 0.032(2) 0.029(2) -0.0024(16) 0.0092(16) 0.0069(17)
C3 0.041(2) 0.031(2) 0.038(2) 0.0006(17) 0.0168(18) -0.0022(18)
C5 0.034(2) 0.035(2) 0.039(2) -0.0036(17) 0.0158(18) 0.0026(17)
C6 0.032(2) 0.040(2) 0.044(2) 0.0040(18) 0.0151(18) -0.0020(18)
C7 0.037(2) 0.032(2) 0.038(2) 0.0046(17) -0.0002(18) -0.0100(17)
C8 0.052(3) 0.030(2) 0.033(2) -0.0032(16) 0.0115(19) -0.0027(18)
C9 0.035(2) 0.0291(19) 0.0248(19) 0.0014(15) 0.0061(16) -0.0003(16)
C1' 0.035(2) 0.0291(19) 0.0287(19) -0.0052(16) 0.0056(16) 0.0002(17)
C2' 0.042(2) 0.030(2) 0.035(2) 0.0016(16) 0.0130(18) 0.0021(17)
C3' 0.037(2) 0.037(2) 0.040(2) -0.0043(18) 0.0088(18) 0.0055(18)
C4' 0.032(2) 0.041(2) 0.036(2) -0.0083(17) 0.0120(17) -0.0089(17)
C5' 0.045(2) 0.0290(19) 0.040(2) 0.0002(17) 0.0100(19) -0.0053(18)
C6' 0.032(2) 0.0310(19) 0.040(2) 0.0031(17) 0.0098(17) 0.0055(16)
C4" 0.055(3) 0.026(2) 0.063(3) -0.012(2) 0.036(2) -0.010(2)
C5" 0.045(2) 0.050(2) 0.039(2) -0.017(2) 0.0234(19) -0.021(2)
C6" 0.033(2) 0.038(2) 0.031(2) 0.0005(17) 0.0070(17) -0.0054(17)
C7" 0.033(2) 0.0219(18) 0.039(2) -0.0021(15) 0.0136(17) -0.0022(15)
C8" 0.035(2) 0.028(2) 0.042(2) 0.0051(17) 0.0118(19) 0.0017(17)
C9" 0.041(2) 0.026(2) 0.066(3) 0.004(2) 0.027(2) 0.0017(18)

_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
Br1 C4' 1.890(4) . ?
O1 C3 1.195(4) . ?
O2 N2 1.236(4) . ?
O3 N2 1.233(4) . ?
O4 N3 1.238(6) . ?
O5 N3 1.218(6) . ?
O6 N5 1.377(4) . ?
O6 N4 1.395(5) . ?
N1 C5 1.348(4) . ?
N1 C9 1.356(4) . ?
N1 C7" 1.521(4) . ?
N2 C6" 1.396(5) . ?
N3 C4" 1.414(5) . ?
N4 C9" 1.312(5) . ?
N5 C8" 1.301(5) . ?
C1 C2 1.338(5) . ?
C1 C9 1.448(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.476(5) . ?
C2 C1' 1.480(5) . ?
C3 C7" 1.554(5) . ?
C5 C6 1.359(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.374(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.373(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.378(5) . ?
C8 H8A 0.9300 . ?
C1' C6' 1.384(5) . ?
C1' C2' 1.391(5) . ?
C2' C3' 1.385(5) . ?
C2' H2'A 0.9300 . ?
C3' C4' 1.376(5) . ?
C3' H3'A 0.9300 . ?
C4' C5' 1.373(5) . ?
C5' C6' 1.378(5) . ?
C5' H5'A 0.9300 . ?
C6' H6'A 0.9300 . ?
C4" C5" 1.374(6) . ?
C4" C9" 1.428(6) . ?
C5" C6" 1.364(5) . ?
C5" H5"A 0.9300 . ?
C6" C7" 1.506(5) . ?
C7" C8" 1.496(5) . ?
C8" C9" 1.405(5) . ?

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
N5 O6 N4 111.0(3) . . ?
C5 N1 C9 120.7(3) . . ?
C5 N1 C7" 117.2(3) . . ?
C9 N1 C7" 122.1(3) . . ?
O3 N2 O2 122.4(4) . . ?
O3 N2 C6" 120.4(4) . . ?
O2 N2 C6" 117.2(3) . . ?
O5 N3 O4 122.9(5) . . ?
O5 N3 C4" 118.4(6) . . ?
O4 N3 C4" 118.8(5) . . ?
C9" N4 O6 104.8(3) . . ?
C8" N5 O6 104.9(3) . . ?
C2 C1 C9 125.2(3) . . ?
C2 C1 H1A 117.4 . . ?
C9 C1 H1A 117.4 . . ?
C1 C2 C3 118.2(3) . . ?
C1 C2 C1' 124.1(3) . . ?
C3 C2 C1' 117.6(3) . . ?
O1 C3 C2 123.5(3) . . ?
O1 C3 C7" 116.3(3) . . ?
C2 C3 C7" 120.2(3) . . ?
N1 C5 C6 121.7(3) . . ?
N1 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C5 C6 C7 119.0(3) . . ?
C5 C6 H6A 120.5 . . ?
C7 C6 H6A 120.5 . . ?
C8 C7 C6 119.0(3) . . ?
C8 C7 H7A 120.5 . . ?
C6 C7 H7A 120.5 . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 H8A 119.4 . . ?
C9 C8 H8A 119.4 . . ?
N1 C9 C8 118.3(3) . . ?
N1 C9 C1 120.5(3) . . ?
C8 C9 C1 121.2(3) . . ?
C6' C1' C2' 119.0(3) . . ?
C6' C1' C2 121.1(3) . . ?
C2' C1' C2 119.9(3) . . ?
C3' C2' C1' 120.4(3) . . ?
C3' C2' H2'A 119.8 . . ?
C1' C2' H2'A 119.8 . . ?
C4' C3' C2' 119.2(3) . . ?
C4' C3' H3'A 120.4 . . ?
C2' C3' H3'A 120.4 . . ?
C5' C4' C3' 121.1(3) . . ?
C5' C4' Br1 119.2(3) . . ?
C3' C4' Br1 119.6(3) . . ?
C4' C5' C6' 119.5(4) . . ?
C4' C5' H5'A 120.2 . . ?
C6' C5' H5'A 120.2 . . ?
C5' C6' C1' 120.7(3) . . ?
C5' C6' H6'A 119.7 . . ?
C1' C6' H6'A 119.7 . . ?
C5" C4" N3 119.8(4) . . ?
C5" C4" C9" 117.6(3) . . ?
N3 C4" C9" 122.5(4) . . ?
C6" C5" C4" 124.3(4) . . ?
C6" C5" H5"A 117.9 . . ?
C4" C5" H5"A 117.9 . . ?
C5" C6" N2 120.0(4) . . ?
C5" C6" C7" 124.6(4) . . ?
N2 C6" C7" 115.0(3) . . ?
C8" C7" C6" 107.1(3) . . ?
C8" C7" N1 108.2(3) . . ?
C6" C7" N1 110.4(3) . . ?
C8" C7" C3 106.9(3) . . ?
C6" C7" C3 110.5(3) . . ?
N1 C7" C3 113.5(3) . . ?
N5 C8" C9" 110.4(4) . . ?
N5 C8" C7" 122.6(3) . . ?
C9" C8" C7" 127.1(4) . . ?
N4 C9" C8" 109.0(4) . . ?
N4 C9" C4" 132.2(4) . . ?
C8" C9" C4" 118.8(4) . . ?

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
N5 O6 N4 C9" 0.2(4) . . . . ?
N4 O6 N5 C8" -0.6(4) . . . . ?
C9 C1 C2 C3 -3.8(6) . . . . ?
C9 C1 C2 C1' 179.3(4) . . . . ?
C1 C2 C3 O1 -173.6(4) . . . . ?
C1' C2 C3 O1 3.5(6) . . . . ?
C1 C2 C3 C7" 7.9(5) . . . . ?
C1' C2 C3 C7" -175.0(3) . . . . ?
C9 N1 C5 C6 -1.2(6) . . . . ?
C7" N1 C5 C6 179.8(3) . . . . ?
N1 C5 C6 C7 0.4(6) . . . . ?
C5 C6 C7 C8 -0.7(6) . . . . ?
C6 C7 C8 C9 1.7(6) . . . . ?
C5 N1 C9 C8 2.1(5) . . . . ?
C7" N1 C9 C8 -178.9(3) . . . . ?
C5 N1 C9 C1 -176.0(3) . . . . ?
C7" N1 C9 C1 3.0(5) . . . . ?
C7 C8 C9 N1 -2.5(5) . . . . ?
C7 C8 C9 C1 175.6(4) . . . . ?
C2 C1 C9 N1 -1.8(6) . . . . ?
C2 C1 C9 C8 -179.8(4) . . . . ?
C1 C2 C1' C6' -131.3(4) . . . . ?
C3 C2 C1' C6' 51.8(5) . . . . ?
C1 C2 C1' C2' 50.0(5) . . . . ?
C3 C2 C1' C2' -127.0(4) . . . . ?
C6' C1' C2' C3' -3.6(5) . . . . ?
C2 C1' C2' C3' 175.2(4) . . . . ?
C1' C2' C3' C4' 2.1(6) . . . . ?
C2' C3' C4' C5' 1.2(6) . . . . ?
C2' C3' C4' Br1 -177.2(3) . . . . ?
C3' C4' C5' C6' -2.9(6) . . . . ?
Br1 C4' C5' C6' 175.5(3) . . . . ?
C4' C5' C6' C1' 1.3(6) . . . . ?
C2' C1' C6' C5' 1.9(6) . . . . ?
C2 C1' C6' C5' -176.8(3) . . . . ?
O5 N3 C4" C5" -177.0(4) . . . . ?
O4 N3 C4" C5" 5.1(6) . . . . ?
O5 N3 C4" C9" 5.4(6) . . . . ?
O4 N3 C4" C9" -172.5(4) . . . . ?
N3 C4" C5" C6" 179.6(3) . . . . ?
C9" C4" C5" C6" -2.8(6) . . . . ?
C4" C5" C6" N2 -176.2(3) . . . . ?
C4" C5" C6" C7" -3.6(6) . . . . ?
O3 N2 C6" C5" -12.2(5) . . . . ?
O2 N2 C6" C5" 169.8(3) . . . . ?
O3 N2 C6" C7" 174.5(3) . . . . ?
O2 N2 C6" C7" -3.6(5) . . . . ?
C5" C6" C7" C8" 7.4(5) . . . . ?
N2 C6" C7" C8" -179.6(3) . . . . ?
C5" C6" C7" N1 125.0(4) . . . . ?
N2 C6" C7" N1 -62.0(4) . . . . ?
C5" C6" C7" C3 -108.7(4) . . . . ?
N2 C6" C7" C3 64.3(4) . . . . ?
C5 N1 C7" C8" 61.6(4) . . . . ?
C9 N1 C7" C8" -117.4(3) . . . . ?
C5 N1 C7" C6" -55.3(4) . . . . ?
C9 N1 C7" C6" 125.7(3) . . . . ?
C5 N1 C7" C3 -180.0(3) . . . . ?
C9 N1 C7" C3 1.0(5) . . . . ?
O1 C3 C7" C8" -65.9(5) . . . . ?
C2 C3 C7" C8" 112.7(4) . . . . ?
O1 C3 C7" C6" 50.4(5) . . . . ?
C2 C3 C7" C6" -131.0(4) . . . . ?
O1 C3 C7" N1 175.0(3) . . . . ?
C2 C3 C7" N1 -6.4(5) . . . . ?
O6 N5 C8" C9" 0.8(4) . . . . ?
O6 N5 C8" C7" 180.0(3) . . . . ?
C6" C7" C8" N5 174.7(3) . . . . ?
N1 C7" C8" N5 55.7(4) . . . . ?
C3 C7" C8" N5 -66.8(4) . . . . ?
C6" C7" C8" C9" -6.3(5) . . . . ?
N1 C7" C8" C9" -125.3(4) . . . . ?
C3 C7" C8" C9" 112.2(4) . . . . ?
O6 N4 C9" C8" 0.3(4) . . . . ?
O6 N4 C9" C4" 179.1(4) . . . . ?
N5 C8" C9" N4 -0.8(5) . . . . ?
C7" C8" C9" N4 -179.9(3) . . . . ?
N5 C8" C9" C4" -179.7(3) . . . . ?
C7" C8" C9" C4" 1.2(6) . . . . ?
C5" C4" C9" N4 -174.8(4) . . . . ?
N3 C4" C9" N4 2.8(7) . . . . ?
C5" C4" C9" C8" 3.9(5) . . . . ?
N3 C4" C9" C8" -178.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.96
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.075


data_tat
_database_code_depnum_ccdc_archive 'CCDC 607711'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H10 Br N5 O5'
_chemical_formula_weight         480.24

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   'I 41/a'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   30.5756(10)
_cell_length_b                   30.5756(10)
_cell_length_c                   7.8321(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7322.0(5)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    987
_cell_measurement_theta_min      5.26
_cell_measurement_theta_max      57.4

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3840
_exptl_absorpt_coefficient_mu    2.294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.550
_exptl_absorpt_correction_T_max  0.635
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1998a)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_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            35505
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_av_sigmaI/netI    0.0670
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         0.94
_diffrn_reflns_theta_max         29.36
_reflns_number_total             5019
_reflns_number_gt                4082
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART (Bruker, 1998b)'
_computing_cell_refinement       'SAINTPlus (Bruker, 1998a)'
_computing_data_reduction        'SAINTPlus (Bruker, 1998a)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'

_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^)+(0.0000P)^2^+0.9000P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5019
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0502
_refine_ls_wR_factor_gt          0.0484
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.327356(8) 1.004930(9) 0.00989(4) 0.02260(6) Uani 1 1 d . . .
C2' C 0.26397(8) 1.09898(8) 0.2977(3) 0.0192(6) Uani 1 1 d . . .
H2'A H 0.2368 1.1019 0.3500 0.023 Uiso 1 1 calc R . .
O2 O 0.35829(6) 1.27033(6) 0.3311(2) 0.0276(5) Uani 1 1 d . . .
N5 N 0.33975(7) 1.12138(7) 0.6487(3) 0.0195(5) Uani 1 1 d . . .
N2 N 0.38559(7) 1.26677(7) 0.4451(3) 0.0215(5) Uani 1 1 d . . .
C1' C 0.29408(8) 1.13303(8) 0.3082(3) 0.0172(6) Uani 1 1 d . . .
O6 O 0.36478(6) 1.09139(5) 0.7334(2) 0.0230(4) Uani 1 1 d . . .
O4 O 0.51251(6) 1.19790(6) 0.7253(3) 0.0326(5) Uani 1 1 d . . .
O5 O 0.48928(6) 1.13700(6) 0.8364(2) 0.0266(5) Uani 1 1 d . . .
N4 N 0.40703(7) 1.10623(7) 0.7631(3) 0.0214(5) Uani 1 1 d . . .
C5 C 0.29649(9) 1.27519(8) 0.6243(3) 0.0192(6) Uani 1 1 d . . .
H5B H 0.3241 1.2770 0.6735 0.023 Uiso 1 1 calc R . .
C9" C 0.40749(9) 1.14566(8) 0.6936(3) 0.0180(6) Uani 1 1 d . . .
C3 C 0.31001(8) 1.20267(7) 0.4869(3) 0.0163(6) Uani 1 1 d . . .
C9 C 0.24378(8) 1.23574(8) 0.4568(3) 0.0185(6) Uani 1 1 d . . .
C6" C 0.38916(9) 1.22517(8) 0.5362(3) 0.0174(6) Uani 1 1 d . . .
O3 O 0.41130(6) 1.29611(6) 0.4840(3) 0.0331(5) Uani 1 1 d . . .
C5" C 0.43081(8) 1.21659(8) 0.6071(3) 0.0185(6) Uani 1 1 d . . .
H5"A H 0.4522 1.2382 0.6014 0.022 Uiso 1 1 calc R . .
N1 N 0.28602(6) 1.24032(7) 0.5225(3) 0.0173(5) Uani 1 1 d . . .
C8" C 0.36595(8) 1.15448(8) 0.6202(3) 0.0163(6) Uani 1 1 d . . .
C7" C 0.35405(8) 1.19579(8) 0.5407(3) 0.0164(6) Uani 1 1 d . . .
C4" C 0.44052(9) 1.17814(8) 0.6828(3) 0.0173(6) Uani 1 1 d . . .
C3' C 0.27397(8) 1.06101(8) 0.2107(3) 0.0198(6) Uani 1 1 d . . .
H3'A H 0.2537 1.0384 0.2038 0.024 Uiso 1 1 calc R . .
C6' C 0.33483(8) 1.12791(8) 0.2303(3) 0.0191(6) Uani 1 1 d . . .
H6'A H 0.3553 1.1503 0.2368 0.023 Uiso 1 1 calc R . .
N3 N 0.48368(7) 1.17078(7) 0.7525(3) 0.0214(5) Uani 1 1 d . . .
C7 C 0.22498(9) 1.30494(9) 0.5776(4) 0.0235(6) Uani 1 1 d . . .
H7A H 0.2053 1.3279 0.5921 0.028 Uiso 1 1 calc R . .
C2 C 0.28178(8) 1.17423(8) 0.3941(3) 0.0171(6) Uani 1 1 d . . .
C6 C 0.26698(9) 1.30671(8) 0.6530(3) 0.0217(6) Uani 1 1 d . . .
H6A H 0.2742 1.3301 0.7235 0.026 Uiso 1 1 calc R . .
C4' C 0.31441(8) 1.05688(8) 0.1340(3) 0.0175(6) Uani 1 1 d . . .
C1 C 0.24191(9) 1.19492(8) 0.3750(3) 0.0193(6) Uani 1 1 d . . .
H1A H 0.2178 1.1837 0.3174 0.023 Uiso 1 1 calc R . .
C8 C 0.21368(9) 1.26919(8) 0.4836(4) 0.0223(6) Uani 1 1 d . . .
H8A H 0.1858 1.2671 0.4372 0.027 Uiso 1 1 calc R . .
C5' C 0.34510(8) 1.08982(8) 0.1435(3) 0.0199(6) Uani 1 1 d . . .
H5'A H 0.3723 1.0865 0.0924 0.024 Uiso 1 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
Br1 0.02478(13) 0.01961(13) 0.02341(13) -0.00407(12) 0.00070(13) -0.00011(13)
C2' 0.0163(15) 0.0233(15) 0.0181(16) 0.0008(11) -0.0011(11) 0.0012(11)
O2 0.0238(11) 0.0334(12) 0.0255(12) 0.0121(9) -0.0050(9) -0.0044(9)
N5 0.0237(13) 0.0167(12) 0.0180(13) 0.0001(10) 0.0016(10) 0.0001(10)
N2 0.0242(13) 0.0228(13) 0.0174(13) 0.0033(10) 0.0043(10) -0.0008(10)
C1' 0.0181(14) 0.0201(14) 0.0133(14) 0.0004(11) -0.0023(11) -0.0002(11)
O6 0.0249(10) 0.0181(10) 0.0261(11) 0.0021(9) 0.0024(9) -0.0022(8)
O4 0.0198(12) 0.0338(11) 0.0444(13) 0.0112(10) -0.0055(10) -0.0056(9)
O5 0.0296(12) 0.0209(10) 0.0293(11) 0.0028(9) -0.0099(9) 0.0018(9)
N4 0.0215(12) 0.0219(12) 0.0210(13) 0.0008(11) 0.0014(11) 0.0007(9)
C5 0.0216(15) 0.0176(14) 0.0184(16) 0.0023(11) 0.0004(12) -0.0034(12)
C9" 0.0242(15) 0.0153(14) 0.0146(15) -0.0040(11) 0.0030(11) 0.0033(11)
C3 0.0196(13) 0.0135(13) 0.0159(14) 0.0017(11) 0.0024(12) 0.0000(10)
C9 0.0185(13) 0.0225(15) 0.0144(13) 0.0036(10) 0.0035(11) -0.0003(12)
C6" 0.0207(15) 0.0155(13) 0.0161(15) -0.0017(11) 0.0029(12) 0.0010(11)
O3 0.0404(13) 0.0212(11) 0.0378(14) 0.0073(10) -0.0105(11) -0.0123(10)
C5" 0.0193(15) 0.0185(15) 0.0176(15) -0.0051(12) 0.0033(12) -0.0039(11)
N1 0.0193(11) 0.0160(12) 0.0168(12) 0.0027(10) 0.0037(9) -0.0018(9)
C8" 0.0178(14) 0.0181(14) 0.0130(14) -0.0044(11) 0.0050(11) 0.0006(11)
C7" 0.0202(14) 0.0169(13) 0.0120(14) -0.0033(11) 0.0045(11) 0.0003(11)
C4" 0.0155(14) 0.0216(15) 0.0147(14) -0.0010(11) 0.0007(11) 0.0003(11)
C3' 0.0166(13) 0.0199(14) 0.0230(16) 0.0040(11) -0.0061(11) -0.0052(11)
C6' 0.0229(14) 0.0154(13) 0.0189(15) -0.0012(11) -0.0003(12) -0.0051(11)
N3 0.0207(13) 0.0234(13) 0.0202(13) -0.0063(11) -0.0012(11) 0.0015(10)
C7 0.0292(16) 0.0225(15) 0.0188(15) 0.0052(12) 0.0067(13) 0.0081(13)
C2 0.0186(15) 0.0172(15) 0.0154(15) 0.0028(11) 0.0055(12) -0.0005(11)
C6 0.0309(17) 0.0155(14) 0.0187(15) -0.0014(12) 0.0071(12) -0.0035(12)
C4' 0.0242(15) 0.0169(14) 0.0114(14) -0.0007(11) 0.0002(11) 0.0037(11)
C1 0.0187(14) 0.0243(14) 0.0150(14) 0.0010(11) 0.0029(12) -0.0042(12)
C8 0.0203(14) 0.0268(15) 0.0199(15) 0.0060(13) 0.0039(12) 0.0029(11)
C5' 0.0172(14) 0.0240(15) 0.0184(15) 0.0002(12) 0.0025(11) 0.0037(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
Br1 C4' 1.904(2) . ?
C2' C3' 1.381(3) . ?
C2' C1' 1.392(3) . ?
C2' H2'A 0.9300 . ?
O2 N2 1.227(3) . ?
N5 C8" 1.310(3) . ?
N5 O6 1.366(3) . ?
N2 O3 1.231(3) . ?
N2 C6" 1.463(3) . ?
C1' C6' 1.396(3) . ?
C1' C2 1.477(3) . ?
O6 N4 1.389(3) . ?
O4 N3 1.229(2) . ?
O5 N3 1.236(2) . ?
N4 C9" 1.323(3) . ?
C5 C6 1.339(3) . ?
C5 N1 1.370(3) . ?
C5 H5B 0.9300 . ?
C9" C4" 1.419(4) . ?
C9" C8" 1.420(3) . ?
C3 N1 1.393(3) . ?
C3 C2 1.424(3) . ?
C3 C7" 1.427(3) . ?
C9 C8 1.392(3) . ?
C9 N1 1.397(3) . ?
C9 C1 1.404(3) . ?
C6" C7" 1.400(3) . ?
C6" C5" 1.414(4) . ?
C5" C4" 1.350(3) . ?
C5" H5"A 0.9300 . ?
C8" C7" 1.455(4) . ?
C4" N3 1.446(3) . ?
C3' C4' 1.381(3) . ?
C3' H3'A 0.9300 . ?
C6' C5' 1.384(3) . ?
C6' H6'A 0.9300 . ?
C7 C8 1.362(4) . ?
C7 C6 1.414(4) . ?
C7 H7A 0.9300 . ?
C2 C1 1.382(4) . ?
C6 H6A 0.9300 . ?
C4' C5' 1.379(3) . ?
C1 H1A 0.9300 . ?
C8 H8A 0.9300 . ?
C5' H5'A 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' C2' C1' 120.8(2) . . ?
C3' C2' H2'A 119.6 . . ?
C1' C2' H2'A 119.6 . . ?
C8" N5 O6 105.0(2) . . ?
O2 N2 O3 123.3(2) . . ?
O2 N2 C6" 118.9(2) . . ?
O3 N2 C6" 117.8(2) . . ?
C2' C1' C6' 118.7(2) . . ?
C2' C1' C2 119.8(2) . . ?
C6' C1' C2 121.5(2) . . ?
N5 O6 N4 112.53(17) . . ?
C9" N4 O6 103.8(2) . . ?
C6 C5 N1 120.0(2) . . ?
C6 C5 H5B 120.0 . . ?
N1 C5 H5B 120.0 . . ?
N4 C9" C4" 132.1(3) . . ?
N4 C9" C8" 109.3(2) . . ?
C4" C9" C8" 118.6(2) . . ?
N1 C3 C2 106.7(2) . . ?
N1 C3 C7" 124.0(2) . . ?
C2 C3 C7" 129.2(2) . . ?
C8 C9 N1 118.8(2) . . ?
C8 C9 C1 134.1(3) . . ?
N1 C9 C1 107.1(2) . . ?
C7" C6" C5" 124.2(2) . . ?
C7" C6" N2 120.9(2) . . ?
C5" C6" N2 114.8(2) . . ?
C4" C5" C6" 122.2(2) . . ?
C4" C5" H5"A 118.9 . . ?
C6" C5" H5"A 118.9 . . ?
C5 N1 C3 129.6(2) . . ?
C5 N1 C9 120.6(2) . . ?
C3 N1 C9 109.3(2) . . ?
N5 C8" C9" 109.3(2) . . ?
N5 C8" C7" 126.2(2) . . ?
C9" C8" C7" 124.2(2) . . ?
C6" C7" C3 128.4(2) . . ?
C6" C7" C8" 112.1(2) . . ?
C3 C7" C8" 119.4(2) . . ?
C5" C4" C9" 118.6(3) . . ?
C5" C4" N3 120.2(2) . . ?
C9" C4" N3 121.2(2) . . ?
C4' C3' C2' 119.3(2) . . ?
C4' C3' H3'A 120.3 . . ?
C2' C3' H3'A 120.3 . . ?
C5' C6' C1' 120.7(2) . . ?
C5' C6' H6'A 119.6 . . ?
C1' C6' H6'A 119.6 . . ?
O4 N3 O5 123.8(2) . . ?
O4 N3 C4" 119.0(2) . . ?
O5 N3 C4" 117.2(2) . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 H7A 120.4 . . ?
C6 C7 H7A 120.4 . . ?
C1 C2 C3 108.1(2) . . ?
C1 C2 C1' 124.4(2) . . ?
C3 C2 C1' 126.8(2) . . ?
C5 C6 C7 120.9(3) . . ?
C5 C6 H6A 119.5 . . ?
C7 C6 H6A 119.5 . . ?
C5' C4' C3' 121.3(2) . . ?
C5' C4' Br1 119.72(19) . . ?
C3' C4' Br1 119.0(2) . . ?
C2 C1 C9 108.8(2) . . ?
C2 C1 H1A 125.6 . . ?
C9 C1 H1A 125.6 . . ?
C7 C8 C9 120.2(3) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C4' C5' C6' 119.1(2) . . ?
C4' C5' H5'A 120.4 . . ?
C6' C5' H5'A 120.4 . . ?

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' C2' C1' C6' -0.6(4) . . . . ?
C3' C2' C1' C2 176.8(2) . . . . ?
C8" N5 O6 N4 1.7(2) . . . . ?
N5 O6 N4 C9" -0.6(3) . . . . ?
O6 N4 C9" C4" 178.9(3) . . . . ?
O6 N4 C9" C8" -0.7(3) . . . . ?
O2 N2 C6" C7" -22.6(3) . . . . ?
O3 N2 C6" C7" 159.6(2) . . . . ?
O2 N2 C6" C5" 153.7(2) . . . . ?
O3 N2 C6" C5" -24.1(3) . . . . ?
C7" C6" C5" C4" 1.7(4) . . . . ?
N2 C6" C5" C4" -174.5(2) . . . . ?
C6 C5 N1 C3 -174.3(2) . . . . ?
C6 C5 N1 C9 -4.2(4) . . . . ?
C2 C3 N1 C5 171.8(2) . . . . ?
C7" C3 N1 C5 -6.9(4) . . . . ?
C2 C3 N1 C9 0.8(3) . . . . ?
C7" C3 N1 C9 -177.9(2) . . . . ?
C8 C9 N1 C5 5.8(3) . . . . ?
C1 C9 N1 C5 -173.5(2) . . . . ?
C8 C9 N1 C3 177.7(2) . . . . ?
C1 C9 N1 C3 -1.5(3) . . . . ?
O6 N5 C8" C9" -2.1(3) . . . . ?
O6 N5 C8" C7" -176.7(2) . . . . ?
N4 C9" C8" N5 1.9(3) . . . . ?
C4" C9" C8" N5 -177.8(2) . . . . ?
N4 C9" C8" C7" 176.6(2) . . . . ?
C4" C9" C8" C7" -3.1(4) . . . . ?
C5" C6" C7" C3 173.9(3) . . . . ?
N2 C6" C7" C3 -10.2(4) . . . . ?
C5" C6" C7" C8" -2.6(4) . . . . ?
N2 C6" C7" C8" 173.3(2) . . . . ?
N1 C3 C7" C6" -43.7(4) . . . . ?
C2 C3 C7" C6" 137.9(3) . . . . ?
N1 C3 C7" C8" 132.6(3) . . . . ?
C2 C3 C7" C8" -45.8(4) . . . . ?
N5 C8" C7" C6" 177.2(2) . . . . ?
C9" C8" C7" C6" 3.3(3) . . . . ?
N5 C8" C7" C3 0.3(4) . . . . ?
C9" C8" C7" C3 -173.5(2) . . . . ?
C6" C5" C4" C9" -1.0(4) . . . . ?
C6" C5" C4" N3 179.6(2) . . . . ?
N4 C9" C4" C5" -177.9(3) . . . . ?
C8" C9" C4" C5" 1.7(4) . . . . ?
N4 C9" C4" N3 1.5(4) . . . . ?
C8" C9" C4" N3 -178.9(2) . . . . ?
C1' C2' C3' C4' 0.3(4) . . . . ?
C2' C1' C6' C5' 0.3(4) . . . . ?
C2 C1' C6' C5' -177.0(2) . . . . ?
C5" C4" N3 O4 -7.9(4) . . . . ?
C9" C4" N3 O4 172.7(2) . . . . ?
C5" C4" N3 O5 172.3(2) . . . . ?
C9" C4" N3 O5 -7.0(3) . . . . ?
N1 C3 C2 C1 0.2(3) . . . . ?
C7" C3 C2 C1 178.9(2) . . . . ?
N1 C3 C2 C1' 171.1(2) . . . . ?
C7" C3 C2 C1' -10.3(4) . . . . ?
C2' C1' C2 C1 -42.5(4) . . . . ?
C6' C1' C2 C1 134.9(3) . . . . ?
C2' C1' C2 C3 148.1(3) . . . . ?
C6' C1' C2 C3 -34.6(4) . . . . ?
N1 C5 C6 C7 -0.8(4) . . . . ?
C8 C7 C6 C5 4.2(4) . . . . ?
C2' C3' C4' C5' 0.4(4) . . . . ?
C2' C3' C4' Br1 -178.59(18) . . . . ?
C3 C2 C1 C9 -1.2(3) . . . . ?
C1' C2 C1 C9 -172.3(2) . . . . ?
C8 C9 C1 C2 -177.4(3) . . . . ?
N1 C9 C1 C2 1.7(3) . . . . ?
C6 C7 C8 C9 -2.5(4) . . . . ?
N1 C9 C8 C7 -2.3(4) . . . . ?
C1 C9 C8 C7 176.7(3) . . . . ?
C3' C4' C5' C6' -0.7(4) . . . . ?
Br1 C4' C5' C6' 178.28(19) . . . . ?
C1' C6' C5' C4' 0.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.36
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.073