# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_str1241
_database_code_depnum_ccdc_archive 'CCDC 882688'
_audit_update_record             
;
2012-05-17 deposited with the CCDC.
2015-02-09 downloaded from the CCDC.
;
#TrackingRef 'archive_Xv2m.cif'


_audit_creation_date             2011-11-14T23:22:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C11 H10 Br1 N3 O1'
_chemical_formula_sum            'C11 H10 Br1 N3 O1'
_chemical_formula_weight         280.12
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

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                   13.5334(6)
_cell_length_b                   12.3004(8)
_cell_length_c                   28.098(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.177(6)
_cell_angle_gamma                90
_cell_volume                     4572.1(5)
_cell_formula_units_Z            16
_cell_measurement_temperature    294(2)

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2240
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.578
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_av_unetI/netI     0.0923
_diffrn_reflns_number            50022
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         29.36
_diffrn_reflns_theta_full        29.36
_diffrn_measured_fraction_theta_full 0.91
_diffrn_measured_fraction_theta_max 0.91
_reflns_number_total             11446
_reflns_number_gt                5333
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0376P)²+8.9544P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         11446
_refine_ls_number_parameters     594
_refine_ls_number_restraints     246
_refine_ls_R_factor_all          0.1773
_refine_ls_R_factor_gt           0.0789
_refine_ls_wR_factor_ref         0.179
_refine_ls_wR_factor_gt          0.1448
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.094

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.28353(5) 0.26066(7) 0.48681(3) 0.0647(2) Uani 1 1 d D A .
C1 C -0.3132(4) 0.2527(6) 0.4940(2) 0.0541(18) Uani 1 1 d D . .
C2 C -0.3804(4) 0.3369(6) 0.4920(2) 0.0541(18) Uani 1 1 d D . .
O3 O -0.4715(3) 0.2991(4) 0.49425(17) 0.0666(14) Uani 1 1 d D . .
N4 N -0.4645(4) 0.1816(4) 0.49670(19) 0.0514(14) Uani 1 1 d D A .
C5 C -0.3693(5) 0.1570(5) 0.4972(2) 0.0535(18) Uani 1 1 d D A .
C6 C -0.057(2) 0.245(3) 0.489(5) 0.095(11) Uani 0.5 1 d PDU A 1
C7 C 0.0039(6) 0.1569(8) 0.5025(3) 0.089(3) Uani 1 1 d D . .
H7 H -0.0225 0.0935 0.5129 0.106 Uiso 1 1 calc R A 1
C8 C 0.1037(5) 0.1618(6) 0.5005(2) 0.064(2) Uani 1 1 d D A .
H8 H 0.1441 0.1001 0.5069 0.077 Uiso 1 1 calc R . .
C9 C 0.1443(4) 0.2585(6) 0.4890(2) 0.0506(17) Uani 1 1 d D . .
C10 C 0.0867(5) 0.3503(6) 0.4786(3) 0.067(2) Uani 1 1 d D A .
H10 H 0.1145 0.4153 0.4707 0.08 Uiso 1 1 calc R . .
C11 C -0.0146(6) 0.3427(9) 0.4803(3) 0.096(3) Uani 1 1 d D . .
H11 H -0.0546 0.4048 0.4753 0.115 Uiso 1 1 calc R A 1
C12 C -0.3661(6) 0.4564(6) 0.4898(3) 0.072(2) Uani 1 1 d D . .
H12A H -0.4141 0.4858 0.4628 0.108 Uiso 1 1 calc R A .
H12B H -0.2988 0.4716 0.4857 0.108 Uiso 1 1 calc R . .
H12C H -0.376 0.489 0.5195 0.108 Uiso 1 1 calc R . .
C13 C -0.3418(6) 0.0403(6) 0.4982(3) 0.074(2) Uani 1 1 d D . .
H13A H -0.4001 -0.003 0.4997 0.111 Uiso 1 1 calc R A .
H13B H -0.2894 0.026 0.5264 0.111 Uiso 1 1 calc R . .
H13C H -0.3181 0.0224 0.4693 0.111 Uiso 1 1 calc R . .
N1 N -0.2155(7) 0.2850(9) 0.4896(5) 0.045(3) Uani 0.5 1 d PD A 1
N2 N -0.1544(7) 0.2075(9) 0.4955(5) 0.049(2) Uani 0.5 1 d PD A 1
N2A N -0.1667(8) 0.3047(10) 0.4906(5) 0.049(2) Uani 0.5 1 d P A 2
N1A N -0.2068(9) 0.2152(10) 0.4963(5) 0.045(3) Uani 0.5 1 d P A 2
C6A C -0.054(3) 0.251(4) 0.496(5) 0.095(11) Uani 0.5 1 d P A 2
Br2 Br 0.17085(4) -0.00999(6) 0.61772(3) 0.0571(2) Uani 1 1 d D . .
C1B C -0.4271(4) 0.0109(5) 0.62500(19) 0.0403(14) Uani 1 1 d D . .
C2B C -0.4807(4) -0.0860(5) 0.6262(2) 0.0444(15) Uani 1 1 d D . .
O3B O -0.5762(3) -0.0632(4) 0.62574(19) 0.0767(16) Uani 1 1 d D . .
N4B N -0.5877(3) 0.0537(4) 0.62295(17) 0.0356(11) Uani 1 1 d D . .
C5B C -0.4966(4) 0.0928(5) 0.6220(2) 0.0430(15) Uani 1 1 d D . .
C6B C -0.1682(4) -0.0377(5) 0.6245(2) 0.0409(15) Uani 1 1 d D . .
C7B C -0.1253(4) 0.0638(5) 0.6217(2) 0.0481(17) Uani 1 1 d D . .
H7B H -0.1641 0.1263 0.6214 0.058 Uiso 1 1 calc R . .
C8B C -0.0246(4) 0.0717(5) 0.6194(2) 0.0505(17) Uani 1 1 d D . .
H8B H 0.0047 0.1395 0.6174 0.061 Uiso 1 1 calc R . .
C9B C 0.0322(4) -0.0215(5) 0.6199(2) 0.0420(15) Uani 1 1 d D . .
C10B C -0.0091(4) -0.1224(5) 0.6235(2) 0.0501(17) Uani 1 1 d D . .
H10B H 0.0304 -0.1846 0.6244 0.06 Uiso 1 1 calc R . .
C11B C -0.1091(4) -0.1306(5) 0.6257(2) 0.0457(16) Uani 1 1 d D . .
H11B H -0.1376 -0.1988 0.6279 0.055 Uiso 1 1 calc R . .
C12B C -0.4511(5) -0.2025(5) 0.6276(2) 0.0546(18) Uani 1 1 d D . .
H12D H -0.5097 -0.2471 0.6267 0.082 Uiso 1 1 calc R . .
H12E H -0.4022 -0.2168 0.6571 0.082 Uiso 1 1 calc R . .
H12F H -0.4222 -0.2189 0.6 0.082 Uiso 1 1 calc R . .
C13B C -0.4841(5) 0.2125(5) 0.6175(2) 0.0535(17) Uani 1 1 d D . .
H13D H -0.5098 0.2342 0.5843 0.08 Uiso 1 1 calc R . .
H13E H -0.4138 0.2309 0.6268 0.08 Uiso 1 1 calc R . .
H13F H -0.5208 0.2495 0.6384 0.08 Uiso 1 1 calc R . .
N1B N -0.3248(3) 0.0281(4) 0.62301(17) 0.0449(13) Uani 1 1 d D . .
N2B N -0.2714(4) -0.0564(4) 0.62703(17) 0.0433(12) Uani 1 1 d D . .
Br3 Br 0.03543(4) 0.25615(6) 0.73591(3) 0.0540(2) Uani 1 1 d D . .
C1C C -0.5626(4) 0.2442(5) 0.7459(2) 0.0375(14) Uani 1 1 d D . .
C2C C -0.6161(4) 0.3414(4) 0.7476(2) 0.0384(14) Uani 1 1 d D . .
O3C O -0.7119(3) 0.3187(4) 0.74762(19) 0.0717(15) Uani 1 1 d D . .
N4C N -0.7206(3) 0.2035(3) 0.74540(17) 0.0323(11) Uani 1 1 d D . .
C5C C -0.6318(4) 0.1619(5) 0.7436(2) 0.0422(15) Uani 1 1 d D . .
C6C C -0.3034(4) 0.2884(5) 0.7436(2) 0.0376(14) Uani 1 1 d D . .
C7C C -0.2649(4) 0.1884(5) 0.7359(2) 0.0491(17) Uani 1 1 d D . .
H7C H -0.3065 0.1275 0.7321 0.059 Uiso 1 1 calc R . .
C8C C -0.1634(4) 0.1782(5) 0.7338(3) 0.0572(19) Uani 1 1 d D . .
H8C H -0.1368 0.1102 0.7293 0.069 Uiso 1 1 calc R . .
C9C C -0.1030(4) 0.2681(5) 0.7385(2) 0.0377(14) Uani 1 1 d D . .
C10C C -0.1418(4) 0.3692(5) 0.7455(2) 0.0471(16) Uani 1 1 d D . .
H10C H -0.1007 0.4305 0.7486 0.056 Uiso 1 1 calc R . .
C11C C -0.2414(4) 0.3780(5) 0.7480(2) 0.0481(17) Uani 1 1 d D . .
H11C H -0.2678 0.4461 0.7526 0.058 Uiso 1 1 calc R . .
C12C C -0.5824(5) 0.4568(5) 0.7491(2) 0.0507(16) Uani 1 1 d D . .
H12G H -0.6381 0.5036 0.7511 0.076 Uiso 1 1 calc R . .
H12H H -0.5584 0.4733 0.7201 0.076 Uiso 1 1 calc R . .
H12I H -0.5288 0.468 0.777 0.076 Uiso 1 1 calc R . .
C13C C -0.6220(4) 0.0425(5) 0.7409(2) 0.0498(17) Uani 1 1 d D . .
H13G H -0.5528 0.0238 0.7416 0.075 Uiso 1 1 calc R . .
H13H H -0.6639 0.0165 0.7111 0.075 Uiso 1 1 calc R . .
H13I H -0.6431 0.0095 0.768 0.075 Uiso 1 1 calc R . .
N1C N -0.4602(3) 0.2234(4) 0.74372(17) 0.0394(12) Uani 1 1 d D . .
N2C N -0.4061(3) 0.3074(4) 0.74642(17) 0.0371(11) Uani 1 1 d D . .
Br4 Br -0.40221(4) 0.50166(6) 0.63215(3) 0.0593(2) Uani 1 1 d D . .
C1D C 0.1981(4) 0.5058(5) 0.6295(2) 0.0399(14) Uani 1 1 d D . .
C2D C 0.2679(4) 0.5893(5) 0.6330(2) 0.0431(15) Uani 1 1 d D . .
O3D O 0.3578(3) 0.5481(4) 0.62983(16) 0.0564(12) Uani 1 1 d D . .
N4D N 0.3465(3) 0.4323(4) 0.62534(18) 0.0443(13) Uani 1 1 d D . .
C5D C 0.2515(4) 0.4100(5) 0.6254(2) 0.0432(15) Uani 1 1 d D . .
C6D C -0.0614(4) 0.4662(4) 0.6274(2) 0.0364(14) Uani 1 1 d D . .
C7D C -0.1283(4) 0.3812(5) 0.6123(2) 0.0444(15) Uani 1 1 d D . .
H7D H -0.1051 0.3166 0.6014 0.053 Uiso 1 1 calc R . .
C8D C -0.2296(4) 0.3926(5) 0.6136(2) 0.0505(17) Uani 1 1 d D . .
H8D H -0.2746 0.3361 0.6031 0.061 Uiso 1 1 calc R . .
C9D C -0.2629(4) 0.4870(5) 0.6301(2) 0.0435(15) Uani 1 1 d D . .
C10D C -0.1974(4) 0.5722(5) 0.6454(2) 0.0455(16) Uani 1 1 d D . .
H10D H -0.221 0.6364 0.6565 0.055 Uiso 1 1 calc R . .
C11D C -0.0960(4) 0.5610(5) 0.6442(2) 0.0437(15) Uani 1 1 d D . .
H11D H -0.0513 0.6177 0.6547 0.052 Uiso 1 1 calc R . .
C12D C 0.2598(5) 0.7086(5) 0.6378(2) 0.0511(17) Uani 1 1 d D . .
H12J H 0.2822 0.7437 0.6115 0.077 Uiso 1 1 calc R . .
H12K H 0.3012 0.7316 0.6682 0.077 Uiso 1 1 calc R . .
H12L H 0.1907 0.7279 0.6369 0.077 Uiso 1 1 calc R . .
C13D C 0.2175(5) 0.2950(5) 0.6219(3) 0.0551(18) Uani 1 1 d D . .
H13J H 0.1684 0.2846 0.5922 0.083 Uiso 1 1 calc R . .
H13K H 0.1878 0.2779 0.6492 0.083 Uiso 1 1 calc R . .
H13L H 0.2744 0.2483 0.6222 0.083 Uiso 1 1 calc R . .
N1D N 0.0966(3) 0.5277(4) 0.63176(17) 0.0413(12) Uani 1 1 d D . .
N2D N 0.0407(3) 0.4445(4) 0.62402(17) 0.0413(12) Uani 1 1 d D . .



#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C9 1.899(5) . ?
C1 C2 1.372(8) . ?
C1 N1 1.411(10) . ?
C1 C5 1.413(8) . ?
C1 N1A 1.500(14) . ?
C2 O3 1.330(7) . ?
C2 C12 1.486(8) . ?
O3 N4 1.450(7) . ?
N4 C5 1.321(7) . ?
C5 C13 1.481(8) . ?
C6 C7 1.373(16) . ?
C6 C11 1.375(15) . ?
C6 N2 1.437(14) . ?
C7 C8 1.365(9) . ?
C7 C6A 1.39(3) . ?
C8 C9 1.378(8) . ?
C9 C10 1.368(8) . ?
C10 C11 1.385(9) . ?
C11 C6A 1.37(3) . ?
N1 N2 1.249(13) . ?
N2A N1A 1.253(16) . ?
N2A C6A 1.63(3) . ?
Br2 C9B 1.896(5) . ?
C1B C5B 1.368(7) . ?
C1B C2B 1.399(7) . ?
C1B N1B 1.413(6) . ?
C2B O3B 1.320(6) . ?
C2B C12B 1.487(8) . ?
O3B N4B 1.446(6) . ?
N4B C5B 1.330(6) . ?
C5B C13B 1.490(8) . ?
C6B C7B 1.386(8) . ?
C6B C11B 1.392(7) . ?
C6B N2B 1.432(6) . ?
C7B C8B 1.381(7) . ?
C8B C9B 1.378(7) . ?
C9B C10B 1.374(7) . ?
C10B C11B 1.371(7) . ?
N1B N2B 1.258(6) . ?
Br3 C9C 1.896(5) . ?
C1C C5C 1.370(7) . ?
C1C C2C 1.403(7) . ?
C1C N1C 1.424(6) . ?
C2C O3C 1.326(6) . ?
C2C C12C 1.489(7) . ?
O3C N4C 1.423(6) . ?
N4C C5C 1.317(6) . ?
C5C C13C 1.479(7) . ?
C6C C7C 1.370(7) . ?
C6C C11C 1.375(7) . ?
C6C N2C 1.427(6) . ?
C7C C8C 1.393(7) . ?
C8C C9C 1.365(7) . ?
C9C C10C 1.380(7) . ?
C10C C11C 1.369(7) . ?
N1C N2C 1.259(6) . ?
Br4 C9D 1.907(5) . ?
C1D C2D 1.385(7) . ?
C1D C5D 1.399(7) . ?
C1D N1D 1.414(6) . ?
C2D O3D 1.338(6) . ?
C2D C12D 1.480(7) . ?
O3D N4D 1.435(6) . ?
N4D C5D 1.314(6) . ?
C5D C13D 1.484(8) . ?
C6D C11D 1.377(7) . ?
C6D C7D 1.389(7) . ?
C6D N2D 1.430(6) . ?
C7D C8D 1.385(7) . ?
C8D C9D 1.362(7) . ?
C9D C10D 1.382(7) . ?
C10D C11D 1.386(7) . ?
N1D N2D 1.264(6) . ?

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
C2 C1 N1 114.2(7) . . ?
C2 C1 C5 105.7(5) . . ?
N1 C1 C5 140.0(7) . . ?
C2 C1 N1A 148.8(7) . . ?
C5 C1 N1A 105.4(7) . . ?
O3 C2 C1 110.3(6) . . ?
O3 C2 C12 118.6(6) . . ?
C1 C2 C12 131.1(6) . . ?
C2 O3 N4 107.4(5) . . ?
C5 N4 O3 106.4(5) . . ?
N4 C5 C1 110.1(6) . . ?
N4 C5 C13 117.5(6) . . ?
C1 C5 C13 132.2(6) . . ?
C7 C6 C11 119.0(14) . . ?
C7 C6 N2 103.0(13) . . ?
C11 C6 N2 137.3(19) . . ?
C8 C7 C6 120.1(10) . . ?
C8 C7 C6A 120.0(12) . . ?
C7 C8 C9 119.6(7) . . ?
C10 C9 C8 121.7(6) . . ?
C10 C9 Br1 120.4(5) . . ?
C8 C9 Br1 117.8(5) . . ?
C9 C10 C11 117.4(7) . . ?
C6A C11 C10 121.9(12) . . ?
C6 C11 C10 121.6(10) . . ?
N2 N1 C1 112.3(10) . . ?
N1 N2 C6 109.4(12) . . ?
N1A N2A C6A 92.9(15) . . ?
N2A N1A C1 99.4(11) . . ?
C11 C6A C7 118(3) . . ?
C11 C6A N2A 93.2(18) . . ?
C7 C6A N2A 147(2) . . ?
C5B C1B C2B 106.0(5) . . ?
C5B C1B N1B 123.6(5) . . ?
C2B C1B N1B 130.2(5) . . ?
O3B C2B C1B 109.3(5) . . ?
O3B C2B C12B 117.6(5) . . ?
C1B C2B C12B 133.2(5) . . ?
C2B O3B N4B 107.8(5) . . ?
C5B N4B O3B 105.7(4) . . ?
N4B C5B C1B 111.1(5) . . ?
N4B C5B C13B 118.8(5) . . ?
C1B C5B C13B 130.1(5) . . ?
C7B C6B C11B 119.7(5) . . ?
C7B C6B N2B 124.9(5) . . ?
C11B C6B N2B 115.4(5) . . ?
C8B C7B C6B 119.7(6) . . ?
C9B C8B C7B 119.7(6) . . ?
C10B C9B C8B 121.2(5) . . ?
C10B C9B Br2 119.4(4) . . ?
C8B C9B Br2 119.4(4) . . ?
C11B C10B C9B 119.4(6) . . ?
C10B C11B C6B 120.4(6) . . ?
N2B N1B C1B 114.9(5) . . ?
N1B N2B C6B 114.2(5) . . ?
C5C C1C C2C 106.2(4) . . ?
C5C C1C N1C 121.8(5) . . ?
C2C C1C N1C 131.9(5) . . ?
O3C C2C C1C 109.4(5) . . ?
O3C C2C C12C 119.6(5) . . ?
C1C C2C C12C 131.0(5) . . ?
C2C O3C N4C 106.3(4) . . ?
C5C N4C O3C 108.7(4) . . ?
N4C C5C C1C 109.3(5) . . ?
N4C C5C C13C 118.7(5) . . ?
C1C C5C C13C 132.0(5) . . ?
C7C C6C C11C 119.2(5) . . ?
C7C C6C N2C 124.2(5) . . ?
C11C C6C N2C 116.5(5) . . ?
C6C C7C C8C 119.9(5) . . ?
C9C C8C C7C 119.9(6) . . ?
C8C C9C C10C 120.4(5) . . ?
C8C C9C Br3 120.7(4) . . ?
C10C C9C Br3 119.0(4) . . ?
C11C C10C C9C 119.2(5) . . ?
C10C C11C C6C 121.4(6) . . ?
N2C N1C C1C 114.2(5) . . ?
N1C N2C C6C 115.0(4) . . ?
C2D C1D C5D 105.9(4) . . ?
C2D C1D N1D 120.6(5) . . ?
C5D C1D N1D 133.4(5) . . ?
O3D C2D C1D 109.3(5) . . ?
O3D C2D C12D 117.9(5) . . ?
C1D C2D C12D 132.8(5) . . ?
C2D O3D N4D 107.5(4) . . ?
C5D N4D O3D 107.1(4) . . ?
N4D C5D C1D 110.3(5) . . ?
N4D C5D C13D 119.2(5) . . ?
C1D C5D C13D 130.5(5) . . ?
C11D C6D C7D 119.7(5) . . ?
C11D C6D N2D 125.7(5) . . ?
C7D C6D N2D 114.6(5) . . ?
C8D C7D C6D 120.0(5) . . ?
C9D C8D C7D 119.7(5) . . ?
C8D C9D C10D 121.0(5) . . ?
C8D C9D Br4 119.5(4) . . ?
C10D C9D Br4 119.5(4) . . ?
C9D C10D C11D 119.4(5) . . ?
C6D C11D C10D 120.2(5) . . ?
N2D N1D C1D 113.0(5) . . ?
N1D N2D C6D 112.9(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O3 177.2(7) . . . . ?
C5 C1 C2 O3 0.7(7) . . . . ?
N1A C1 C2 O3 -175.7(13) . . . . ?
N1 C1 C2 C12 -5.4(12) . . . . ?
C5 C1 C2 C12 178.1(7) . . . . ?
N1A C1 C2 C12 1.8(19) . . . . ?
C1 C2 O3 N4 -1.5(7) . . . . ?
C12 C2 O3 N4 -179.3(6) . . . . ?
C2 O3 N4 C5 1.7(7) . . . . ?
O3 N4 C5 C1 -1.3(7) . . . . ?
O3 N4 C5 C13 -178.4(5) . . . . ?
C2 C1 C5 N4 0.5(7) . . . . ?
N1 C1 C5 N4 -174.5(10) . . . . ?
N1A C1 C5 N4 178.5(7) . . . . ?
C2 C1 C5 C13 176.9(7) . . . . ?
N1 C1 C5 C13 1.9(16) . . . . ?
N1A C1 C5 C13 -5.0(11) . . . . ?
C11 C6 C7 C8 -9(14) . . . . ?
N2 C6 C7 C8 179(4) . . . . ?
N2 C6 C7 C6A -90(15) . . . . ?
C6 C7 C8 C9 5(7) . . . . ?
C6A C7 C8 C9 -5(7) . . . . ?
C7 C8 C9 C10 -1.0(11) . . . . ?
C7 C8 C9 Br1 179.9(6) . . . . ?
C8 C9 C10 C11 0.2(11) . . . . ?
Br1 C9 C10 C11 179.3(5) . . . . ?
C7 C6 C11 C6A -87(15) . . . . ?
N2 C6 C11 C6A 82(16) . . . . ?
C7 C6 C11 C10 8(14) . . . . ?
N2 C6 C11 C10 177(12) . . . . ?
C9 C10 C11 C6A 6(7) . . . . ?
C9 C10 C11 C6 -4(7) . . . . ?
C2 C1 N1 N2 174.6(10) . . . . ?
C5 C1 N1 N2 -10.7(19) . . . . ?
N1A C1 N1 N2 1.1(13) . . . . ?
C1 N1 N2 C6 179(6) . . . . ?
C7 C6 N2 N1 173(6) . . . . ?
C11 C6 N2 N1 3(17) . . . . ?
C6A N2A N1A C1 178(5) . . . . ?
C2 C1 N1A N2A -7(2) . . . . ?
N1 C1 N1A N2A 4.5(12) . . . . ?
C5 C1 N1A N2A 176.7(9) . . . . ?
C6 C11 C6A C7 79(13) . . . . ?
C10 C11 C6A C7 -12(14) . . . . ?
C10 C11 C6A N2A 177.2(18) . . . . ?
C8 C7 C6A C11 11(14) . . . . ?
C6 C7 C6A C11 -83(17) . . . . ?
C8 C7 C6A N2A 174(15) . . . . ?
C6 C7 C6A N2A 80(18) . . . . ?
N1A N2A C6A C11 168(6) . . . . ?
N1A N2A C6A C7 0E1(2) . . . . ?
C5B C1B C2B O3B -2.3(7) . . . . ?
N1B C1B C2B O3B -177.2(6) . . . . ?
C5B C1B C2B C12B 177.7(7) . . . . ?
N1B C1B C2B C12B 2.7(11) . . . . ?
C1B C2B O3B N4B 1.5(7) . . . . ?
C12B C2B O3B N4B -178.4(5) . . . . ?
C2B O3B N4B C5B -0.1(7) . . . . ?
O3B N4B C5B C1B -1.3(7) . . . . ?
O3B N4B C5B C13B 178.0(5) . . . . ?
C2B C1B C5B N4B 2.2(7) . . . . ?
N1B C1B C5B N4B 177.6(5) . . . . ?
C2B C1B C5B C13B -177.0(6) . . . . ?
N1B C1B C5B C13B -1.6(10) . . . . ?
C11B C6B C7B C8B 0.9(9) . . . . ?
N2B C6B C7B C8B -179.8(6) . . . . ?
C6B C7B C8B C9B -0.1(10) . . . . ?
C7B C8B C9B C10B -1.0(10) . . . . ?
C7B C8B C9B Br2 -179.0(5) . . . . ?
C8B C9B C10B C11B 1.2(10) . . . . ?
Br2 C9B C10B C11B 179.2(5) . . . . ?
C9B C10B C11B C6B -0.4(10) . . . . ?
C7B C6B C11B C10B -0.7(9) . . . . ?
N2B C6B C11B C10B 180.0(5) . . . . ?
C5B C1B N1B N2B 179.1(5) . . . . ?
C2B C1B N1B N2B -6.8(9) . . . . ?
C1B N1B N2B C6B 179.5(5) . . . . ?
C7B C6B N2B N1B 4.8(8) . . . . ?
C11B C6B N2B N1B -175.9(5) . . . . ?
C5C C1C C2C O3C 1.6(7) . . . . ?
N1C C1C C2C O3C 177.8(6) . . . . ?
C5C C1C C2C C12C -178.2(6) . . . . ?
N1C C1C C2C C12C -2.0(11) . . . . ?
C1C C2C O3C N4C -0.6(7) . . . . ?
C12C C2C O3C N4C 179.2(5) . . . . ?
C2C O3C N4C C5C -0.7(7) . . . . ?
O3C N4C C5C C1C 1.7(7) . . . . ?
O3C N4C C5C C13C -179.7(5) . . . . ?
C2C C1C C5C N4C -2.0(7) . . . . ?
N1C C1C C5C N4C -178.7(5) . . . . ?
C2C C1C C5C C13C 179.6(6) . . . . ?
N1C C1C C5C C13C 3.0(10) . . . . ?
C11C C6C C7C C8C 1.7(9) . . . . ?
N2C C6C C7C C8C -179.9(6) . . . . ?
C6C C7C C8C C9C -1.4(10) . . . . ?
C7C C8C C9C C10C 0.5(10) . . . . ?
C7C C8C C9C Br3 179.9(5) . . . . ?
C8C C9C C10C C11C 0.1(10) . . . . ?
Br3 C9C C10C C11C -179.3(5) . . . . ?
C9C C10C C11C C6C 0.2(10) . . . . ?
C7C C6C C11C C10C -1.1(9) . . . . ?
N2C C6C C11C C10C -179.6(6) . . . . ?
C5C C1C N1C N2C -179.8(5) . . . . ?
C2C C1C N1C N2C 4.4(9) . . . . ?
C1C N1C N2C C6C -179.2(4) . . . . ?
C7C C6C N2C N1C 3.5(8) . . . . ?
C11C C6C N2C N1C -178.1(5) . . . . ?
C5D C1D C2D O3D 1.6(7) . . . . ?
N1D C1D C2D O3D -180.0(5) . . . . ?
C5D C1D C2D C12D 179.7(7) . . . . ?
N1D C1D C2D C12D -1.8(10) . . . . ?
C1D C2D O3D N4D -1.5(7) . . . . ?
C12D C2D O3D N4D -179.9(5) . . . . ?
C2D O3D N4D C5D 0.7(7) . . . . ?
O3D N4D C5D C1D 0.3(7) . . . . ?
O3D N4D C5D C13D -179.1(5) . . . . ?
C2D C1D C5D N4D -1.2(7) . . . . ?
N1D C1D C5D N4D -179.3(6) . . . . ?
C2D C1D C5D C13D 178.1(7) . . . . ?
N1D C1D C5D C13D 0.0(11) . . . . ?
C11D C6D C7D C8D 0.9(9) . . . . ?
N2D C6D C7D C8D -179.6(6) . . . . ?
C6D C7D C8D C9D -0.7(10) . . . . ?
C7D C8D C9D C10D 0.5(10) . . . . ?
C7D C8D C9D Br4 -179.5(5) . . . . ?
C8D C9D C10D C11D -0.4(10) . . . . ?
Br4 C9D C10D C11D 179.6(5) . . . . ?
C7D C6D C11D C10D -0.9(9) . . . . ?
N2D C6D C11D C10D 179.7(6) . . . . ?
C9D C10D C11D C6D 0.6(9) . . . . ?
C2D C1D N1D N2D 174.4(5) . . . . ?
C5D C1D N1D N2D -7.6(9) . . . . ?
C1D N1D N2D C6D 178.7(4) . . . . ?
C11D C6D N2D N1D -9.4(8) . . . . ?
C7D C6D N2D N1D 171.2(5) . . . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xv3
_database_code_depnum_ccdc_archive 'CCDC 882689'
_audit_update_record             
;
2012-05-17 deposited with the CCDC.
2015-02-09 downloaded from the CCDC.
;
#TrackingRef 'archive_xv3.cif'


_audit_creation_date             2010-04-28T19:12:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C11 H10 N4 O3'
_chemical_formula_sum            'C11 H10 N4 O3'
_chemical_formula_weight         246.23
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.765(4)
_cell_length_b                   11.314(6)
_cell_length_c                   17.774(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.75(4)
_cell_angle_gamma                90
_cell_volume                     2354(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      6.8
_cell_measurement_theta_max      13.7
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_crystal_density_diffrn    1.39
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.5991
_exptl_absorpt_correction_T_max  0.9802

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      0.000741
_diffrn_orient_matrix_ub_12      0.012945
_diffrn_orient_matrix_ub_13      0.055739
_diffrn_orient_matrix_ub_21      0.079821
_diffrn_orient_matrix_ub_22      0.030997
_diffrn_orient_matrix_ub_23      0.001861
_diffrn_orient_matrix_ub_31      -0.030356
_diffrn_orient_matrix_ub_32      0.081742
_diffrn_orient_matrix_ub_33      -0.009612
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_standards_number         1
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
3 1 3

_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_number            2703
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.3
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             2303
_reflns_number_gt                1102
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/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_number_reflns         2303
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1615
_refine_ls_wR_factor_gt          0.1374
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.15
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.9720(3) 0.1401(3) 0.43730(17) 0.0564(8) Uani 1 1 d . . .
C2 C 0.9755(3) 0.0695(3) 0.3763(2) 0.0632(9) Uani 1 1 d . . .
C5 C 1.0641(3) 0.2214(3) 0.43315(19) 0.0655(9) Uani 1 1 d . . .
C6 C 0.8197(2) 0.1833(3) 0.59509(17) 0.0513(7) Uani 1 1 d . . .
C7 C 0.8245(2) 0.2611(3) 0.65592(16) 0.0500(8) Uani 1 1 d . . .
C8 C 0.7531(2) 0.2552(3) 0.71216(17) 0.0582(8) Uani 1 1 d . . .
H8 H 0.7591 0.3094 0.7517 0.07 Uiso 1 1 calc R . .
C9 C 0.6726(3) 0.1671(3) 0.7084(2) 0.0703(10) Uani 1 1 d . . .
H9 H 0.6233 0.1605 0.746 0.084 Uiso 1 1 calc R . .
C10 C 0.6649(3) 0.0885(3) 0.6491(2) 0.0767(11) Uani 1 1 d . . .
H10 H 0.6101 0.029 0.6471 0.092 Uiso 1 1 calc R . .
C11 C 0.7370(3) 0.0960(3) 0.59210(19) 0.0675(9) Uani 1 1 d . . .
H11 H 0.7298 0.0426 0.5521 0.081 Uiso 1 1 calc R . .
C21 C 0.9044(3) -0.0303(3) 0.34632(18) 0.0813(11) Uani 1 1 d . . .
H21A H 0.8624 -0.0076 0.2994 0.122 Uiso 1 1 calc R . .
H21B H 0.852 -0.0517 0.3821 0.122 Uiso 1 1 calc R . .
H21C H 0.9525 -0.0965 0.3379 0.122 Uiso 1 1 calc R . .
C51 C 1.1034(3) 0.3216(3) 0.4832(2) 0.0835(11) Uani 1 1 d . . .
H51A H 1.1676 0.3593 0.4638 0.125 Uiso 1 1 calc R . .
H51B H 1.1256 0.2926 0.5333 0.125 Uiso 1 1 calc R . .
H51C H 1.0425 0.3777 0.4848 0.125 Uiso 1 1 calc R . .
N1 N 0.8932(2) 0.1246(2) 0.48937(15) 0.0579(7) Uani 1 1 d . . .
N2 N 0.89835(19) 0.2019(2) 0.54042(14) 0.0548(7) Uani 1 1 d . . .
O3 O 1.0613(2) 0.1026(2) 0.33682(13) 0.0844(8) Uani 1 1 d . . .
N7 N 0.9132(3) 0.3528(2) 0.66119(15) 0.0600(7) Uani 1 1 d . . .
O1 O 1.0128(2) 0.3231(2) 0.66607(14) 0.0804(8) Uani 1 1 d . . .
O2 O 0.8824(2) 0.4530(2) 0.66238(18) 0.1103(11) Uani 1 1 d . . .
N4 N 1.1184(3) 0.2006(3) 0.37431(17) 0.0820(9) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C2 1.351(4) . ?
C1 N1 1.385(4) . ?
C1 C5 1.429(4) . ?
C2 O3 1.339(4) . ?
C2 C21 1.472(5) . ?
C5 N4 1.300(4) . ?
C5 C51 1.485(4) . ?
C6 C11 1.384(4) . ?
C6 C7 1.391(4) . ?
C6 N2 1.423(4) . ?
C7 C8 1.370(4) . ?
C7 N7 1.468(4) . ?
C8 C9 1.372(4) . ?
C9 C10 1.376(5) . ?
C10 C11 1.387(5) . ?
N1 N2 1.257(3) . ?
O3 N4 1.426(4) . ?
N7 O2 1.191(3) . ?
N7 O1 1.214(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
C2 C1 N1 122.5(3) . . ?
C2 C1 C5 104.8(3) . . ?
N1 C1 C5 132.7(3) . . ?
O3 C2 C1 109.9(3) . . ?
O3 C2 C21 117.1(3) . . ?
C1 C2 C21 133.0(3) . . ?
N4 C5 C1 111.2(3) . . ?
N4 C5 C51 118.1(3) . . ?
C1 C5 C51 130.7(3) . . ?
C11 C6 C7 117.1(3) . . ?
C11 C6 N2 125.6(3) . . ?
C7 C6 N2 117.3(3) . . ?
C8 C7 C6 123.8(3) . . ?
C8 C7 N7 118.1(3) . . ?
C6 C7 N7 118.1(2) . . ?
C7 C8 C9 118.1(3) . . ?
C8 C9 C10 119.9(3) . . ?
C9 C10 C11 121.5(3) . . ?
C6 C11 C10 119.7(3) . . ?
N2 N1 C1 114.0(3) . . ?
N1 N2 C6 113.7(3) . . ?
C2 O3 N4 108.5(3) . . ?
O2 N7 O1 123.7(3) . . ?
O2 N7 C7 117.3(3) . . ?
O1 N7 C7 119.0(3) . . ?
C5 N4 O3 105.7(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 O3 -178.5(3) . . . . ?
C5 C1 C2 O3 -0.1(3) . . . . ?
N1 C1 C2 C21 2.8(5) . . . . ?
C5 C1 C2 C21 -178.8(3) . . . . ?
C2 C1 C5 N4 -0.2(4) . . . . ?
N1 C1 C5 N4 178.0(3) . . . . ?
C2 C1 C5 C51 179.0(3) . . . . ?
N1 C1 C5 C51 -2.9(6) . . . . ?
C11 C6 C7 C8 0.4(4) . . . . ?
N2 C6 C7 C8 178.9(3) . . . . ?
C11 C6 C7 N7 178.7(3) . . . . ?
N2 C6 C7 N7 -2.8(4) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
N7 C7 C8 C9 -178.0(3) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C7 C6 C11 C10 -0.9(4) . . . . ?
N2 C6 C11 C10 -179.4(3) . . . . ?
C9 C10 C11 C6 0.8(5) . . . . ?
C2 C1 N1 N2 -176.5(3) . . . . ?
C5 C1 N1 N2 5.6(5) . . . . ?
C1 N1 N2 C6 -178.1(2) . . . . ?
C11 C6 N2 N1 -5.2(4) . . . . ?
C7 C6 N2 N1 176.4(3) . . . . ?
C1 C2 O3 N4 0.4(3) . . . . ?
C21 C2 O3 N4 179.3(2) . . . . ?
C8 C7 N7 O2 -59.9(4) . . . . ?
C6 C7 N7 O2 121.7(3) . . . . ?
C8 C7 N7 O1 118.2(3) . . . . ?
C6 C7 N7 O1 -60.2(4) . . . . ?
C1 C5 N4 O3 0.4(4) . . . . ?
C51 C5 N4 O3 -178.9(3) . . . . ?
C2 O3 N4 C5 -0.5(3) . . . . ?



