# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Dr Cehpuri Ramana'
_publ_contact_author_email       VR.CHEPURI@NCL.RES.IN

_publ_section_title              
;
"Click" Synthesis of Isomeric Compounds for Assessing
the Efficiency of Bifurcated Br***NO2 Synthon
;
loop_
_publ_author_name
'Cehpuri Ramana'
'Soumitra Chatterjee'
'Kulbhushan A. Durugkar'
'Rajesh G. Gonnade'

# Attachment 'CIFS_B809985E.cif'

data_8
_database_code_depnum_ccdc_archive 'CCDC 679556'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 N4 O2'
_chemical_formula_sum            'C14 H10 N4 O2'
_chemical_formula_weight         266.26

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   12.180(4)
_cell_length_b                   7.501(3)
_cell_length_c                   14.277(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.286(7)
_cell_angle_gamma                90.00
_cell_volume                     1283.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1175
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      24.79

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9596
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_process_details   'bruker sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9605
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2513
_reflns_number_gt                1661
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'

_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)+(0.0581P)²+0.0999P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2513
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1475
_refine_ls_wR_factor_gt          0.1304
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_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
O1 O 0.69082(19) 0.1782(3) 0.32451(17) 0.0801(7) Uani 1 1 d . . .
O2 O 0.5724(2) 0.1838(3) 0.41958(16) 0.0791(7) Uani 1 1 d . . .
N1 N 0.58043(17) 0.0134(3) 0.15993(14) 0.0460(5) Uani 1 1 d . . .
N2 N 0.5140(2) 0.1600(3) 0.15057(17) 0.0620(7) Uani 1 1 d . . .
N3 N 0.5440(2) 0.2568(3) 0.08300(17) 0.0618(7) Uani 1 1 d . . .
N4 N 0.6154(2) 0.1130(3) 0.35831(16) 0.0539(6) Uani 1 1 d . . .
C1 C 0.6509(2) 0.0187(4) 0.09837(18) 0.0473(7) Uani 1 1 d . . .
C2 C 0.6286(2) 0.1748(3) 0.04925(18) 0.0465(6) Uani 1 1 d . . .
C3 C 0.6822(2) 0.2531(3) -0.02445(17) 0.0459(6) Uani 1 1 d . . .
C4 C 0.6785(3) 0.4383(4) -0.0400(2) 0.0552(8) Uani 1 1 d . . .
C5 C 0.7313(3) 0.5140(5) -0.1078(2) 0.0645(8) Uani 1 1 d . . .
C6 C 0.7896(3) 0.4089(5) -0.1604(2) 0.0697(9) Uani 1 1 d . . .
C7 C 0.7943(3) 0.2263(5) -0.1464(2) 0.0662(9) Uani 1 1 d . . .
C8 C 0.7402(3) 0.1501(4) -0.0793(2) 0.0575(7) Uani 1 1 d . . .
C9 C 0.5700(2) -0.1157(3) 0.23118(18) 0.0433(6) Uani 1 1 d . . .
C10 C 0.5469(2) -0.2919(3) 0.2055(2) 0.0516(7) Uani 1 1 d . . .
C11 C 0.5307(3) -0.4134(4) 0.2742(2) 0.0598(8) Uani 1 1 d . . .
C12 C 0.5345(3) -0.3625(4) 0.3666(2) 0.0638(8) Uani 1 1 d . . .
C13 C 0.5575(2) -0.1863(4) 0.3937(2) 0.0552(7) Uani 1 1 d . . .
C14 C 0.5776(2) -0.0674(3) 0.32556(18) 0.0435(6) Uani 1 1 d . . .
H1 H 0.705(2) -0.068(4) 0.0924(18) 0.064(8) Uiso 1 1 d . . .
H4 H 0.640(2) 0.504(4) -0.0042(19) 0.059(9) Uiso 1 1 d . . .
H5 H 0.729(3) 0.648(4) -0.118(2) 0.084(10) Uiso 1 1 d . . .
H6 H 0.826(2) 0.462(4) -0.204(2) 0.069(9) Uiso 1 1 d . . .
H7 H 0.831(3) 0.148(5) -0.182(2) 0.095(12) Uiso 1 1 d . . .
H8 H 0.742(2) 0.020(4) -0.0709(18) 0.060(8) Uiso 1 1 d . . .
H10 H 0.5418(19) -0.323(3) 0.1398(18) 0.042(7) Uiso 1 1 d . . .
H11 H 0.516(2) -0.535(4) 0.2523(19) 0.073(9) Uiso 1 1 d . . .
H12 H 0.521(2) -0.440(4) 0.414(2) 0.071(9) Uiso 1 1 d . . .
H13 H 0.562(2) -0.148(4) 0.459(2) 0.068(9) Uiso 1 1 d . . .


_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 N4 1.214(3) . ?
O2 N4 1.219(3) . ?
N1 C1 1.334(3) . ?
N1 N2 1.358(3) . ?
N1 C9 1.426(3) . ?
N2 N3 1.310(3) . ?
N3 C2 1.361(3) . ?
N4 C14 1.478(3) . ?
C1 C2 1.367(4) . ?
C2 C3 1.458(3) . ?
C3 C8 1.381(4) . ?
C3 C4 1.406(4) . ?
C4 C5 1.377(4) . ?
C5 C6 1.371(4) . ?
C6 C7 1.384(5) . ?
C7 C8 1.379(4) . ?
C9 C14 1.382(3) . ?
C9 C10 1.387(4) . ?
C10 C11 1.378(4) . ?
C11 C12 1.367(4) . ?
C12 C13 1.392(4) . ?
C13 C14 1.373(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
C1 N1 N2 110.7(2) . . ?
C1 N1 C9 129.8(2) . . ?
N2 N1 C9 119.5(2) . . ?
N3 N2 N1 106.4(2) . . ?
N2 N3 C2 109.8(2) . . ?
O1 N4 O2 124.2(2) . . ?
O1 N4 C14 117.3(2) . . ?
O2 N4 C14 118.4(2) . . ?
N1 C1 C2 105.7(2) . . ?
N3 C2 C1 107.4(2) . . ?
N3 C2 C3 122.6(2) . . ?
C1 C2 C3 130.0(2) . . ?
C8 C3 C4 117.9(3) . . ?
C8 C3 C2 121.6(3) . . ?
C4 C3 C2 120.4(2) . . ?
C5 C4 C3 120.8(3) . . ?
C6 C5 C4 120.0(3) . . ?
C5 C6 C7 120.1(3) . . ?
C8 C7 C6 119.9(3) . . ?
C7 C8 C3 121.2(3) . . ?
C14 C9 C10 118.8(2) . . ?
C14 C9 N1 121.2(2) . . ?
C10 C9 N1 119.9(2) . . ?
C11 C10 C9 119.4(3) . . ?
C12 C11 C10 121.2(3) . . ?
C11 C12 C13 120.3(3) . . ?
C14 C13 C12 118.2(3) . . ?
C13 C14 C9 122.0(2) . . ?
C13 C14 N4 117.1(2) . . ?
C9 C14 N4 120.7(2) . . ?

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
C1 N1 N2 N3 -0.2(3) . . . . ?
C9 N1 N2 N3 177.9(2) . . . . ?
N1 N2 N3 C2 -0.2(3) . . . . ?
N2 N1 C1 C2 0.5(3) . . . . ?
C9 N1 C1 C2 -177.3(2) . . . . ?
N2 N3 C2 C1 0.5(3) . . . . ?
N2 N3 C2 C3 -178.0(2) . . . . ?
N1 C1 C2 N3 -0.6(3) . . . . ?
N1 C1 C2 C3 177.7(3) . . . . ?
N3 C2 C3 C8 -158.7(3) . . . . ?
C1 C2 C3 C8 23.2(4) . . . . ?
N3 C2 C3 C4 23.0(4) . . . . ?
C1 C2 C3 C4 -155.2(3) . . . . ?
C8 C3 C4 C5 -0.1(4) . . . . ?
C2 C3 C4 C5 178.3(3) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C4 C5 C6 C7 0.8(5) . . . . ?
C5 C6 C7 C8 0.0(5) . . . . ?
C6 C7 C8 C3 -0.9(5) . . . . ?
C4 C3 C8 C7 0.9(4) . . . . ?
C2 C3 C8 C7 -177.5(3) . . . . ?
C1 N1 C9 C14 123.6(3) . . . . ?
N2 N1 C9 C14 -54.1(3) . . . . ?
C1 N1 C9 C10 -59.2(4) . . . . ?
N2 N1 C9 C10 123.1(3) . . . . ?
C14 C9 C10 C11 0.9(4) . . . . ?
N1 C9 C10 C11 -176.3(2) . . . . ?
C9 C10 C11 C12 1.4(5) . . . . ?
C10 C11 C12 C13 -1.4(5) . . . . ?
C11 C12 C13 C14 -0.9(5) . . . . ?
C12 C13 C14 C9 3.3(4) . . . . ?
C12 C13 C14 N4 -172.6(3) . . . . ?
C10 C9 C14 C13 -3.4(4) . . . . ?
N1 C9 C14 C13 173.8(2) . . . . ?
C10 C9 C14 N4 172.5(2) . . . . ?
N1 C9 C14 N4 -10.3(4) . . . . ?
O1 N4 C14 C13 136.9(3) . . . . ?
O2 N4 C14 C13 -40.4(3) . . . . ?
O1 N4 C14 C9 -39.2(3) . . . . ?
O2 N4 C14 C9 143.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O1 0.94(3) 2.47(3) 3.270(3) 143(2) 2_645
C11 H11 N2 0.97(3) 2.71(3) 3.642(4) 162(2) 1_545
C13 H13 O2 0.97(3) 2.59(3) 3.334(4) 133(2) 3_656

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.036

#===END

data_9
_database_code_depnum_ccdc_archive 'CCDC 679557'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Br N4 O2'
_chemical_formula_sum            'C14 H9 Br N4 O2'
_chemical_formula_weight         345.16

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           MONOCLINIC
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   12.388(13)
_cell_length_b                   8.051(9)
_cell_length_c                   14.256(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.305(18)
_cell_angle_gamma                90.00
_cell_volume                     1384(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1834
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      22.37

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ORANGE
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.68
_exptl_crystal_size_min          0.54
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.981
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.2074
_exptl_absorpt_correction_T_max  0.2959
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6344
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_sigmaI/netI    0.0648
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2419
_reflns_number_gt                1685
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0830P)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    RIDING
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2419
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1376
_refine_ls_wR_factor_gt          0.1245
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_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 0.78644(5) 1.01839(6) 0.43023(4) 0.0829(3) Uani 1 1 d . . .
O1 O 0.6820(3) 0.8034(5) 0.8341(2) 0.0966(10) Uani 1 1 d . . .
O2 O 0.5582(3) 0.8225(6) 0.9164(3) 0.1144(13) Uani 1 1 d . . .
N1 N 0.5919(3) 0.9578(4) 0.6590(2) 0.0592(8) Uani 1 1 d . . .
N2 N 0.5227(3) 0.8285(5) 0.6439(3) 0.0887(12) Uani 1 1 d . . .
N3 N 0.5497(3) 0.7372(5) 0.5769(3) 0.0823(11) Uani 1 1 d . . .
N4 N 0.6073(3) 0.8757(5) 0.8584(3) 0.0761(10) Uani 1 1 d . . .
C1 C 0.6632(3) 0.9479(5) 0.6007(3) 0.0552(9) Uani 1 1 d . . .
H1 H 0.7190 1.0231 0.5968 0.066 Uiso 1 1 calc R . .
C2 C 0.6375(3) 0.8074(5) 0.5491(2) 0.0559(9) Uani 1 1 d . . .
C3 C 0.6843(3) 0.7187(5) 0.4778(2) 0.0546(9) Uani 1 1 d . . .
C4 C 0.6628(4) 0.5499(5) 0.4635(3) 0.0653(11) Uani 1 1 d . . .
H4 H 0.6194 0.4973 0.4999 0.078 Uiso 1 1 calc R . .
C5 C 0.7027(4) 0.4584(6) 0.3988(4) 0.0791(14) Uani 1 1 d . . .
H5 H 0.6854 0.3462 0.3906 0.095 Uiso 1 1 calc R . .
C6 C 0.7689(4) 0.5329(6) 0.3452(4) 0.0797(14) Uani 1 1 d . . .
H6 H 0.7984 0.4704 0.3022 0.096 Uiso 1 1 calc R . .
C7 C 0.7908(4) 0.6981(6) 0.3555(3) 0.0707(11) Uani 1 1 d . . .
H7 H 0.8339 0.7494 0.3184 0.085 Uiso 1 1 calc R . .
C8 C 0.7492(3) 0.7897(5) 0.4210(2) 0.0595(10) Uani 1 1 d . . .
C9 C 0.5802(3) 1.0819(5) 0.7253(3) 0.0550(9) Uani 1 1 d . . .
C10 C 0.5635(3) 1.2447(5) 0.6959(3) 0.0673(11) Uani 1 1 d . . .
H10 H 0.5654 1.2735 0.6331 0.081 Uiso 1 1 calc R . .
C11 C 0.5438(3) 1.3654(6) 0.7585(4) 0.0806(13) Uani 1 1 d . . .
H11 H 0.5347 1.4754 0.7384 0.097 Uiso 1 1 calc R . .
C12 C 0.5378(3) 1.3234(7) 0.8497(4) 0.0866(14) Uani 1 1 d . . .
H12 H 0.5218 1.4047 0.8908 0.104 Uiso 1 1 calc R . .
C13 C 0.5554(3) 1.1608(7) 0.8820(3) 0.0767(13) Uani 1 1 d . . .
H13 H 0.5515 1.1327 0.9444 0.092 Uiso 1 1 calc R . .
C14 C 0.5784(3) 1.0429(5) 0.8206(3) 0.0601(10) Uani 1 1 d . . .


_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 C8 1.895(4) . ?
O1 N4 1.209(4) . ?
O2 N4 1.212(4) . ?
N1 N2 1.334(5) . ?
N1 C1 1.348(5) . ?
N1 C9 1.405(5) . ?
N2 N3 1.308(5) . ?
N3 C2 1.363(5) . ?
N4 C14 1.463(6) . ?
C1 C2 1.347(5) . ?
C2 C3 1.467(5) . ?
C3 C8 1.388(5) . ?
C3 C4 1.391(5) . ?
C4 C5 1.359(6) . ?
C5 C6 1.381(7) . ?
C6 C7 1.358(6) . ?
C7 C8 1.380(5) . ?
C9 C10 1.377(6) . ?
C9 C14 1.400(6) . ?
C10 C11 1.378(6) . ?
C11 C12 1.363(7) . ?
C12 C13 1.388(7) . ?
C13 C14 1.365(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
N2 N1 C1 110.0(3) . . ?
N2 N1 C9 120.1(3) . . ?
C1 N1 C9 129.8(3) . . ?
N3 N2 N1 107.0(3) . . ?
N2 N3 C2 109.6(3) . . ?
O1 N4 O2 124.2(4) . . ?
O1 N4 C14 118.4(4) . . ?
O2 N4 C14 117.2(4) . . ?
C2 C1 N1 106.3(3) . . ?
C1 C2 N3 107.1(3) . . ?
C1 C2 C3 134.9(4) . . ?
N3 C2 C3 118.0(3) . . ?
C8 C3 C4 115.7(4) . . ?
C8 C3 C2 125.3(3) . . ?
C4 C3 C2 119.0(4) . . ?
C5 C4 C3 122.8(4) . . ?
C4 C5 C6 119.7(5) . . ?
C7 C6 C5 119.6(4) . . ?
C6 C7 C8 120.0(4) . . ?
C7 C8 C3 122.1(4) . . ?
C7 C8 Br1 116.3(3) . . ?
C3 C8 Br1 121.6(3) . . ?
C10 C9 C14 118.3(4) . . ?
C10 C9 N1 120.2(4) . . ?
C14 C9 N1 121.4(4) . . ?
C9 C10 C11 120.7(4) . . ?
C12 C11 C10 120.0(5) . . ?
C11 C12 C13 120.8(5) . . ?
C14 C13 C12 118.9(4) . . ?
C13 C14 C9 121.3(4) . . ?
C13 C14 N4 118.3(4) . . ?
C9 C14 N4 120.4(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5 Br1 0.93 2.92 3.690(6) 141.1 1_545
C13 H13 O2 0.93 2.68 3.482(6) 145.4 3_677
C1 H1 O1 0.93 2.65 3.451(6) 145.0 2_656

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.073

#===END

data_10
_database_code_depnum_ccdc_archive 'CCDC 679558'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Br N4 O2'
_chemical_formula_sum            'C14 H9 Br N4 O2'
_chemical_formula_weight         345.16

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           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                   9.2835(11)
_cell_length_b                   7.2943(9)
_cell_length_c                   20.794(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.444(2)
_cell_angle_gamma                90.00
_cell_volume                     1396.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2171
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      22.20

_exptl_crystal_description       PLATE
_exptl_crystal_colour            ORANGE
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.954
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.3142
_exptl_absorpt_correction_T_max  0.7001
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8147
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2448
_reflns_number_gt                1881
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0449P)²+0.6717P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2448
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_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 -0.35384(4) 0.67164(6) 0.017641(17) 0.08172(19) Uani 1 1 d . . .
O1 O 0.3640(3) 0.8414(4) 0.31455(17) 0.1016(10) Uani 1 1 d . . .
O2 O 0.4556(3) 0.8569(3) 0.41448(19) 0.0994(10) Uani 1 1 d . . .
N1 N 0.0863(2) 0.6940(3) 0.31547(11) 0.0459(5) Uani 1 1 d . . .
N2 N 0.0615(3) 0.8586(3) 0.34212(12) 0.0540(6) Uani 1 1 d . . .
N3 N -0.0251(3) 0.9486(3) 0.29872(12) 0.0544(6) Uani 1 1 d . . .
N4 N 0.3809(3) 0.7831(4) 0.36969(19) 0.0671(8) Uani 1 1 d . . .
C1 C 0.0155(3) 0.6812(4) 0.25556(14) 0.0493(7) Uani 1 1 d . . .
H1 H 0.0148 0.5822 0.2273 0.059 Uiso 1 1 calc R . .
C2 C -0.0559(3) 0.8441(4) 0.24450(13) 0.0454(6) Uani 1 1 d . . .
C3 C -0.1491(3) 0.9078(4) 0.18638(14) 0.0453(6) Uani 1 1 d . . .
C4 C -0.1827(3) 1.0923(4) 0.17716(16) 0.0536(7) Uani 1 1 d . . .
H4 H -0.1512 1.1769 0.2094 0.064 Uiso 1 1 calc R . .
C5 C -0.2632(3) 1.1503(4) 0.11997(17) 0.0615(8) Uani 1 1 d . . .
H5 H -0.2838 1.2744 0.1139 0.074 Uiso 1 1 calc R . .
C6 C -0.3129(3) 1.0275(5) 0.07226(16) 0.0610(8) Uani 1 1 d . . .
H6 H -0.3664 1.0674 0.0339 0.073 Uiso 1 1 calc R . .
C7 C -0.2821(3) 0.8436(4) 0.08212(14) 0.0543(7) Uani 1 1 d . . .
C8 C -0.2015(3) 0.7824(4) 0.13845(14) 0.0500(7) Uani 1 1 d . . .
H8 H -0.1823 0.6580 0.1444 0.060 Uiso 1 1 calc R . .
C9 C 0.1769(3) 0.5613(4) 0.35132(13) 0.0432(6) Uani 1 1 d . . .
C10 C 0.1269(3) 0.3857(4) 0.35846(15) 0.0532(7) Uani 1 1 d . . .
H10 H 0.0352 0.3524 0.3384 0.064 Uiso 1 1 calc R . .
C11 C 0.2115(4) 0.2590(4) 0.39510(16) 0.0600(8) Uani 1 1 d . . .
H11 H 0.1773 0.1403 0.3991 0.072 Uiso 1 1 calc R . .
C12 C 0.3467(4) 0.3071(4) 0.42597(15) 0.0572(8) Uani 1 1 d . . .
H12 H 0.4028 0.2218 0.4514 0.069 Uiso 1 1 calc R . .
C13 C 0.3981(3) 0.4816(4) 0.41901(14) 0.0539(7) Uani 1 1 d . . .
H13 H 0.4889 0.5153 0.4399 0.065 Uiso 1 1 calc R . .
C14 C 0.3151(3) 0.6055(4) 0.38121(14) 0.0459(7) Uani 1 1 d . . .


_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 C7 1.893(3) . ?
O1 N4 1.214(4) . ?
O2 N4 1.213(4) . ?
N1 C1 1.335(4) . ?
N1 N2 1.354(3) . ?
N1 C9 1.427(3) . ?
N2 N3 1.306(3) . ?
N3 C2 1.360(3) . ?
N4 C14 1.465(4) . ?
C1 C2 1.366(4) . ?
C2 C3 1.467(4) . ?
C3 C4 1.389(4) . ?
C3 C8 1.393(4) . ?
C4 C5 1.386(4) . ?
C5 C6 1.372(5) . ?
C6 C7 1.381(4) . ?
C7 C8 1.380(4) . ?
C9 C10 1.378(4) . ?
C9 C14 1.389(4) . ?
C10 C11 1.377(4) . ?
C11 C12 1.379(5) . ?
C12 C13 1.374(4) . ?
C13 C14 1.368(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
C1 N1 N2 110.8(2) . . ?
C1 N1 C9 128.7(2) . . ?
N2 N1 C9 120.5(2) . . ?
N3 N2 N1 106.6(2) . . ?
N2 N3 C2 109.6(2) . . ?
O2 N4 O1 124.2(3) . . ?
O2 N4 C14 118.4(3) . . ?
O1 N4 C14 117.3(3) . . ?
N1 C1 C2 105.4(2) . . ?
N3 C2 C1 107.6(2) . . ?
N3 C2 C3 122.9(2) . . ?
C1 C2 C3 129.4(3) . . ?
C4 C3 C8 119.0(3) . . ?
C4 C3 C2 121.2(3) . . ?
C8 C3 C2 119.7(3) . . ?
C5 C4 C3 120.1(3) . . ?
C6 C5 C4 121.0(3) . . ?
C5 C6 C7 118.9(3) . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 Br1 119.3(2) . . ?
C6 C7 Br1 119.4(2) . . ?
C7 C8 C3 119.7(3) . . ?
C10 C9 C14 118.2(3) . . ?
C10 C9 N1 120.2(3) . . ?
C14 C9 N1 121.6(2) . . ?
C11 C10 C9 120.5(3) . . ?
C10 C11 C12 120.5(3) . . ?
C13 C12 C11 119.6(3) . . ?
C14 C13 C12 119.7(3) . . ?
C13 C14 C9 121.5(3) . . ?
C13 C14 N4 117.6(3) . . ?
C9 C14 N4 120.8(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
C1 N1 N2 N3 0.0(3) . . . . ?
C9 N1 N2 N3 -179.4(2) . . . . ?
N1 N2 N3 C2 -0.2(3) . . . . ?
N2 N1 C1 C2 0.1(3) . . . . ?
C9 N1 C1 C2 179.5(2) . . . . ?
N2 N3 C2 C1 0.2(3) . . . . ?
N2 N3 C2 C3 -179.1(3) . . . . ?
N1 C1 C2 N3 -0.2(3) . . . . ?
N1 C1 C2 C3 179.0(3) . . . . ?
N3 C2 C3 C4 15.9(4) . . . . ?
C1 C2 C3 C4 -163.3(3) . . . . ?
N3 C2 C3 C8 -166.1(3) . . . . ?
C1 C2 C3 C8 14.7(4) . . . . ?
C8 C3 C4 C5 -2.2(4) . . . . ?
C2 C3 C4 C5 175.8(3) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C5 C6 C7 Br1 178.5(2) . . . . ?
C6 C7 C8 C3 -0.4(4) . . . . ?
Br1 C7 C8 C3 -179.6(2) . . . . ?
C4 C3 C8 C7 1.8(4) . . . . ?
C2 C3 C8 C7 -176.2(3) . . . . ?
C1 N1 C9 C10 -52.4(4) . . . . ?
N2 N1 C9 C10 126.9(3) . . . . ?
C1 N1 C9 C14 129.3(3) . . . . ?
N2 N1 C9 C14 -51.3(4) . . . . ?
C14 C9 C10 C11 0.9(4) . . . . ?
N1 C9 C10 C11 -177.4(3) . . . . ?
C9 C10 C11 C12 1.0(5) . . . . ?
C10 C11 C12 C13 -1.3(5) . . . . ?
C11 C12 C13 C14 -0.4(5) . . . . ?
C12 C13 C14 C9 2.4(4) . . . . ?
C12 C13 C14 N4 -173.6(3) . . . . ?
C10 C9 C14 C13 -2.6(4) . . . . ?
N1 C9 C14 C13 175.7(2) . . . . ?
C10 C9 C14 N4 173.2(3) . . . . ?
N1 C9 C14 N4 -8.5(4) . . . . ?
O2 N4 C14 C13 -40.6(4) . . . . ?
O1 N4 C14 C13 134.9(3) . . . . ?
O2 N4 C14 C9 143.4(3) . . . . ?
O1 N4 C14 C9 -41.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O1 0.93 2.32 3.153(4) 149.6 2_545
C11 H11 N2 0.93 2.54 3.360(4) 147.3 1_545

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.051

#===END

data_11
_database_code_depnum_ccdc_archive 'CCDC 679559'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Br N4 O2'
_chemical_formula_sum            'C14 H9 Br N4 O2'
_chemical_formula_weight         345.16

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           MONOCLINIC
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   5.4468(9)
_cell_length_b                   20.778(3)
_cell_length_c                   12.482(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.427(3)
_cell_angle_gamma                90.00
_cell_volume                     1379.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2192
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      23.75

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            ORANGE
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.989
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.2357
_exptl_absorpt_correction_T_max  0.5862
_exptl_absorpt_process_details   "BRUKER'S SADABS"

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6843
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         24.98
_reflns_number_total             2427
_reflns_number_gt                1896
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0368P)²+0.9060P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    REFALL
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2427
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.09857(8) 0.460922(19) 0.89370(3) 0.07820(18) Uani 1 1 d . . .
O1 O 0.2517(5) 0.24496(15) 0.2699(2) 0.0882(9) Uani 1 1 d . . .
O2 O 0.4529(5) 0.23384(14) 0.1406(2) 0.0833(8) Uani 1 1 d . . .
N1 N 0.0340(4) 0.36601(12) 0.24565(18) 0.0468(6) Uani 1 1 d . . .
N2 N 0.2754(5) 0.38603(15) 0.2731(2) 0.0631(8) Uani 1 1 d . . .
N3 N 0.3146(5) 0.40533(15) 0.3749(2) 0.0615(7) Uani 1 1 d . . .
N4 N 0.2784(5) 0.25457(13) 0.1766(2) 0.0579(7) Uani 1 1 d . . .
C1 C -0.0786(6) 0.37326(15) 0.3307(2) 0.0444(7) Uani 1 1 d . . .
C2 C 0.1012(5) 0.39805(14) 0.4135(2) 0.0441(7) Uani 1 1 d . . .
C3 C 0.0951(5) 0.41362(14) 0.5281(2) 0.0448(7) Uani 1 1 d . . .
C4 C 0.2834(7) 0.45110(15) 0.5900(3) 0.0526(8) Uani 1 1 d . . .
C5 C 0.2856(7) 0.46510(15) 0.6988(3) 0.0558(8) Uani 1 1 d . . .
C6 C 0.0962(6) 0.44130(14) 0.7446(2) 0.0510(7) Uani 1 1 d . . .
C7 C -0.0926(7) 0.40371(17) 0.6852(3) 0.0575(8) Uani 1 1 d . . .
C8 C -0.0930(6) 0.39040(17) 0.5770(3) 0.0537(8) Uani 1 1 d . . .
C9 C -0.0557(5) 0.33853(14) 0.1399(2) 0.0450(7) Uani 1 1 d . . .
C10 C -0.2678(6) 0.36273(16) 0.0705(3) 0.0540(8) Uani 1 1 d . . .
C11 C -0.3401(7) 0.33877(18) -0.0347(3) 0.0622(9) Uani 1 1 d . . .
C12 C -0.1981(7) 0.29362(18) -0.0729(3) 0.0640(9) Uani 1 1 d . . .
C13 C 0.0114(7) 0.26863(17) -0.0047(3) 0.0564(8) Uani 1 1 d . . .
C14 C 0.0771(5) 0.28958(14) 0.1022(2) 0.0459(7) Uani 1 1 d . . .
H1 H -0.233(6) 0.3620(13) 0.325(2) 0.038(7) Uiso 1 1 d . . .
H4 H 0.404(6) 0.4664(14) 0.560(3) 0.053(9) Uiso 1 1 d . . .
H5 H 0.414(7) 0.4931(18) 0.740(3) 0.075(11) Uiso 1 1 d . . .
H7 H -0.228(7) 0.3862(18) 0.718(3) 0.083(11) Uiso 1 1 d . . .
H8 H -0.214(6) 0.3651(16) 0.541(3) 0.061(10) Uiso 1 1 d . . .
H10 H -0.347(6) 0.3939(15) 0.095(2) 0.049(9) Uiso 1 1 d . . .
H11 H -0.483(7) 0.3549(17) -0.077(3) 0.075(11) Uiso 1 1 d . . .
H12 H -0.245(7) 0.2801(17) -0.147(3) 0.080(11) Uiso 1 1 d . . .
H13 H 0.109(6) 0.2364(16) -0.027(3) 0.058(9) Uiso 1 1 d . . .


_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 C6 1.903(3) . ?
O1 N4 1.220(3) . ?
O2 N4 1.215(3) . ?
N1 C1 1.344(4) . ?
N1 N2 1.351(3) . ?
N1 C9 1.425(3) . ?
N2 N3 1.306(3) . ?
N3 C2 1.359(4) . ?
N4 C14 1.469(4) . ?
C1 C2 1.362(4) . ?
C2 C3 1.475(4) . ?
C3 C4 1.383(4) . ?
C3 C8 1.387(4) . ?
C4 C5 1.386(4) . ?
C5 C6 1.374(5) . ?
C6 C7 1.374(5) . ?
C7 C8 1.378(4) . ?
C9 C10 1.381(4) . ?
C9 C14 1.387(4) . ?
C10 C11 1.380(5) . ?
C11 C12 1.365(5) . ?
C12 C13 1.370(5) . ?
C13 C14 1.376(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
C1 N1 N2 110.5(2) . . ?
C1 N1 C9 130.8(3) . . ?
N2 N1 C9 118.6(2) . . ?
N3 N2 N1 106.7(2) . . ?
N2 N3 C2 109.7(2) . . ?
O2 N4 O1 124.0(3) . . ?
O2 N4 C14 118.6(3) . . ?
O1 N4 C14 117.3(3) . . ?
N1 C1 C2 105.4(3) . . ?
N3 C2 C1 107.7(3) . . ?
N3 C2 C3 121.2(2) . . ?
C1 C2 C3 131.0(3) . . ?
C4 C3 C8 118.6(3) . . ?
C4 C3 C2 119.8(3) . . ?
C8 C3 C2 121.6(3) . . ?
C3 C4 C5 120.9(3) . . ?
C6 C5 C4 118.9(3) . . ?
C5 C6 C7 121.5(3) . . ?
C5 C6 Br1 118.8(2) . . ?
C7 C6 Br1 119.7(2) . . ?
C6 C7 C8 119.0(3) . . ?
C7 C8 C3 121.0(3) . . ?
C10 C9 C14 118.7(3) . . ?
C10 C9 N1 120.6(3) . . ?
C14 C9 N1 120.5(2) . . ?
C11 C10 C9 119.7(3) . . ?
C12 C11 C10 120.8(3) . . ?
C11 C12 C13 120.2(3) . . ?
C12 C13 C14 119.3(3) . . ?
C13 C14 C9 121.0(3) . . ?
C13 C14 N4 117.4(3) . . ?
C9 C14 N4 121.4(2) . . ?

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
C1 N1 N2 N3 0.4(4) . . . . ?
C9 N1 N2 N3 -176.2(3) . . . . ?
N1 N2 N3 C2 -0.1(4) . . . . ?
N2 N1 C1 C2 -0.6(3) . . . . ?
C9 N1 C1 C2 175.5(3) . . . . ?
N2 N3 C2 C1 -0.3(4) . . . . ?
N2 N3 C2 C3 177.4(3) . . . . ?
N1 C1 C2 N3 0.5(3) . . . . ?
N1 C1 C2 C3 -176.9(3) . . . . ?
N3 C2 C3 C4 16.8(4) . . . . ?
C1 C2 C3 C4 -166.1(3) . . . . ?
N3 C2 C3 C8 -161.8(3) . . . . ?
C1 C2 C3 C8 15.2(5) . . . . ?
C8 C3 C4 C5 0.3(5) . . . . ?
C2 C3 C4 C5 -178.4(3) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C7 0.6(5) . . . . ?
C4 C5 C6 Br1 -179.7(2) . . . . ?
C5 C6 C7 C8 -0.9(5) . . . . ?
Br1 C6 C7 C8 179.4(2) . . . . ?
C6 C7 C8 C3 0.8(5) . . . . ?
C4 C3 C8 C7 -0.6(5) . . . . ?
C2 C3 C8 C7 178.1(3) . . . . ?
C1 N1 C9 C10 58.6(4) . . . . ?
N2 N1 C9 C10 -125.6(3) . . . . ?
C1 N1 C9 C14 -125.4(3) . . . . ?
N2 N1 C9 C14 50.4(4) . . . . ?
C14 C9 C10 C11 -1.2(5) . . . . ?
N1 C9 C10 C11 174.9(3) . . . . ?
C9 C10 C11 C12 -3.2(5) . . . . ?
C10 C11 C12 C13 3.9(6) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C12 C13 C14 C9 -4.3(5) . . . . ?
C12 C13 C14 N4 170.7(3) . . . . ?
C10 C9 C14 C13 4.9(4) . . . . ?
N1 C9 C14 C13 -171.2(3) . . . . ?
C10 C9 C14 N4 -169.9(3) . . . . ?
N1 C9 C14 N4 14.0(4) . . . . ?
O2 N4 C14 C13 36.0(4) . . . . ?
O1 N4 C14 C13 -139.9(3) . . . . ?
O2 N4 C14 C9 -149.0(3) . . . . ?
O1 N4 C14 C9 35.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 N2 0.86(3) 2.66(3) 3.447(4) 152(2) 1_455

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.052

#===END

data_12
_database_code_depnum_ccdc_archive 'CCDC 679560'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 N4 O2'
_chemical_formula_sum            'C14 H10 N4 O2'
_chemical_formula_weight         266.26

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.502(3)
_cell_length_b                   5.3559(18)
_cell_length_c                   27.363(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.564(6)
_cell_angle_gamma                90.00
_cell_volume                     1240.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2172
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9696
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_process_details   'bruker sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5402
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2170
_reflns_number_gt                1779
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'

_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)+(0.0564P)²+0.4985P] 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_extinction_coef       ?
_refine_ls_number_reflns         2170
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1260
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_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
O1 O 0.0029(2) 1.0378(3) 0.44121(6) 0.0626(5) Uani 1 1 d . . .
O2 O 0.0521(2) 0.9861(4) 0.36626(7) 0.0679(5) Uani 1 1 d . . .
N1 N 0.2947(2) 0.3584(3) 0.53720(7) 0.0434(5) Uani 1 1 d . . .
N2 N 0.3655(2) 0.1365(4) 0.54893(8) 0.0573(6) Uani 1 1 d . . .
N3 N 0.3657(2) 0.1069(4) 0.59611(8) 0.0573(6) Uani 1 1 d . . .
N4 N 0.0679(2) 0.9265(4) 0.40952(7) 0.0464(5) Uani 1 1 d . . .
C1 C 0.2507(2) 0.4711(4) 0.57811(8) 0.0421(5) Uani 1 1 d . . .
H1 H 0.2004 0.6245 0.5801 0.051 Uiso 1 1 calc R . .
C2 C 0.2963(2) 0.3098(4) 0.61595(8) 0.0438(5) Uani 1 1 d . . .
C3 C 0.2794(2) 0.3287(4) 0.66883(8) 0.0451(5) Uani 1 1 d . . .
C4 C 0.3532(3) 0.1575(5) 0.70171(10) 0.0612(7) Uani 1 1 d . . .
H4 H 0.4150 0.0316 0.6901 0.073 Uiso 1 1 calc R . .
C5 C 0.3365(4) 0.1709(6) 0.75107(10) 0.0730(8) Uani 1 1 d . . .
H5 H 0.3870 0.0548 0.7724 0.088 Uiso 1 1 calc R . .
C6 C 0.2456(3) 0.3548(6) 0.76895(10) 0.0671(7) Uani 1 1 d . . .
H6 H 0.2339 0.3632 0.8024 0.081 Uiso 1 1 calc R . .
C7 C 0.1716(3) 0.5273(6) 0.73707(10) 0.0693(8) Uani 1 1 d . . .
H7 H 0.1101 0.6526 0.7491 0.083 Uiso 1 1 calc R . .
C8 C 0.1885(3) 0.5148(5) 0.68750(10) 0.0614(7) Uani 1 1 d . . .
H8 H 0.1384 0.6322 0.6663 0.074 Uiso 1 1 calc R . .
C9 C 0.2794(2) 0.4419(4) 0.48744(8) 0.0403(5) Uani 1 1 d . . .
C10 C 0.3627(2) 0.3174(4) 0.45310(9) 0.0474(6) Uani 1 1 d . . .
H10 H 0.4283 0.1836 0.4628 0.057 Uiso 1 1 calc R . .
C11 C 0.3468(3) 0.3946(5) 0.40495(9) 0.0527(6) Uani 1 1 d . . .
H11 H 0.4023 0.3118 0.3822 0.063 Uiso 1 1 calc R . .
C12 C 0.2501(3) 0.5929(5) 0.38968(8) 0.0496(6) Uani 1 1 d . . .
H12 H 0.2392 0.6438 0.3570 0.060 Uiso 1 1 calc R . .
C13 C 0.1700(2) 0.7130(4) 0.42458(8) 0.0403(5) Uani 1 1 d . . .
C14 C 0.1825(2) 0.6417(4) 0.47330(8) 0.0413(5) Uani 1 1 d . . .
H14 H 0.1273 0.7259 0.4960 0.050 Uiso 1 1 calc R . .


_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 N4 1.227(2) . ?
O2 N4 1.221(2) . ?
N1 C1 1.356(3) . ?
N1 N2 1.357(3) . ?
N1 C9 1.427(3) . ?
N2 N3 1.300(3) . ?
N3 C2 1.373(3) . ?
N4 C13 1.471(3) . ?
C1 C2 1.375(3) . ?
C2 C3 1.471(3) . ?
C3 C8 1.389(3) . ?
C3 C4 1.391(3) . ?
C4 C5 1.374(4) . ?
C5 C6 1.371(4) . ?
C6 C7 1.380(4) . ?
C7 C8 1.379(4) . ?
C9 C14 1.383(3) . ?
C9 C10 1.399(3) . ?
C10 C11 1.375(3) . ?
C11 C12 1.383(3) . ?
C12 C13 1.384(3) . ?
C13 C14 1.381(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
C1 N1 N2 110.26(18) . . ?
C1 N1 C9 129.89(18) . . ?
N2 N1 C9 119.84(17) . . ?
N3 N2 N1 107.42(18) . . ?
N2 N3 C2 109.69(19) . . ?
O2 N4 O1 122.9(2) . . ?
O2 N4 C13 118.79(18) . . ?
O1 N4 C13 118.28(19) . . ?
N1 C1 C2 105.18(19) . . ?
N3 C2 C1 107.45(19) . . ?
N3 C2 C3 122.0(2) . . ?
C1 C2 C3 130.5(2) . . ?
C8 C3 C4 117.9(2) . . ?
C8 C3 C2 121.5(2) . . ?
C4 C3 C2 120.7(2) . . ?
C5 C4 C3 121.2(2) . . ?
C6 C5 C4 120.3(3) . . ?
C5 C6 C7 119.6(3) . . ?
C8 C7 C6 120.3(3) . . ?
C7 C8 C3 120.7(2) . . ?
C14 C9 C10 120.5(2) . . ?
C14 C9 N1 120.41(18) . . ?
C10 C9 N1 119.08(19) . . ?
C11 C10 C9 119.4(2) . . ?
C10 C11 C12 121.4(2) . . ?
C11 C12 C13 117.8(2) . . ?
C14 C13 C12 122.7(2) . . ?
C14 C13 N4 118.28(18) . . ?
C12 C13 N4 119.0(2) . . ?
C13 C14 C9 118.17(19) . . ?

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
C1 N1 N2 N3 0.5(2) . . . . ?
C9 N1 N2 N3 179.24(18) . . . . ?
N1 N2 N3 C2 -0.5(3) . . . . ?
N2 N1 C1 C2 -0.3(2) . . . . ?
C9 N1 C1 C2 -178.86(19) . . . . ?
N2 N3 C2 C1 0.3(3) . . . . ?
N2 N3 C2 C3 179.92(19) . . . . ?
N1 C1 C2 N3 0.0(2) . . . . ?
N1 C1 C2 C3 -179.6(2) . . . . ?
N3 C2 C3 C8 -170.1(2) . . . . ?
C1 C2 C3 C8 9.4(4) . . . . ?
N3 C2 C3 C4 9.1(3) . . . . ?
C1 C2 C3 C4 -171.4(2) . . . . ?
C8 C3 C4 C5 0.2(4) . . . . ?
C2 C3 C4 C5 -179.0(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C5 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 C3 0.2(4) . . . . ?
C4 C3 C8 C7 -0.4(4) . . . . ?
C2 C3 C8 C7 178.8(2) . . . . ?
C1 N1 C9 C14 -13.8(3) . . . . ?
N2 N1 C9 C14 167.76(19) . . . . ?
C1 N1 C9 C10 166.8(2) . . . . ?
N2 N1 C9 C10 -11.7(3) . . . . ?
C14 C9 C10 C11 -0.3(3) . . . . ?
N1 C9 C10 C11 179.08(19) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C11 C12 C13 N4 179.20(19) . . . . ?
O2 N4 C13 C14 -177.73(19) . . . . ?
O1 N4 C13 C14 2.6(3) . . . . ?
O2 N4 C13 C12 2.7(3) . . . . ?
O1 N4 C13 C12 -176.9(2) . . . . ?
C12 C13 C14 C9 0.0(3) . . . . ?
N4 C13 C14 C9 -179.58(18) . . . . ?
C10 C9 C14 C13 0.4(3) . . . . ?
N1 C9 C14 C13 -179.05(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O1 0.93 2.53 3.409(3) 157.6 3_576
C14 H14 O1 0.93 2.48 3.408(3) 176.2 3_576
C8 H8 O2 0.93 2.70 3.593(3) 160.1 3_576
C6 H6 O2 0.93 2.57 3.372(3) 144.2 4_576
C10 H10 N2 0.93 2.50 3.358(3) 154.4 3_656

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.038

#===END

data_13
_database_code_depnum_ccdc_archive 'CCDC 679561'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Br N4 O2'
_chemical_formula_sum            'C14 H9 Br N4 O2'
_chemical_formula_weight         345.16

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           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                   7.228(7)
_cell_length_b                   13.308(13)
_cell_length_c                   14.521(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.675(19)
_cell_angle_gamma                90.00
_cell_volume                     1394(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1537
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      19.18

_exptl_crystal_description       'thin needle'
_exptl_crystal_colour            ornage
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2120
_exptl_absorpt_correction_T_max  0.8518
_exptl_absorpt_process_details   'bruker sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9670
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2455
_reflns_number_gt                1522
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.1525P)²+25.1020P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2455
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1755
_refine_ls_R_factor_gt           0.1357
_refine_ls_wR_factor_ref         0.4175
_refine_ls_wR_factor_gt          0.3958
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.141
_refine_ls_shift/su_max          0.000
_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 1.1266(3) 0.89950(16) 0.35563(13) 0.0868(10) Uani 1 1 d . . .
O1 O 0.557(2) 1.1992(11) -0.1824(8) 0.084(4) Uani 1 1 d . . .
O2 O 0.566(2) 1.3534(12) -0.1436(9) 0.098(5) Uani 1 1 d . . .
N1 N 0.8338(16) 1.0121(9) 0.0898(7) 0.046(3) Uani 1 1 d . . .
N2 N 0.760(2) 0.9408(11) 0.0332(9) 0.073(4) Uani 1 1 d . . .
N3 N 0.797(2) 0.8547(11) 0.0711(10) 0.076(5) Uani 1 1 d . . .
N4 N 0.600(2) 1.2663(12) -0.1288(9) 0.065(4) Uani 1 1 d . . .
C1 C 0.916(2) 0.9677(12) 0.1646(10) 0.057(4) Uani 1 1 d . . .
H1 H 0.9757 1.0001 0.2149 0.069 Uiso 1 1 calc R . .
C2 C 0.898(2) 0.8693(12) 0.1539(10) 0.054(4) Uani 1 1 d . . .
C3 C 0.958(2) 0.7779(12) 0.2068(11) 0.057(4) Uani 1 1 d . . .
C4 C 0.916(3) 0.6844(13) 0.1694(13) 0.070(5) Uani 1 1 d . . .
H4 H 0.8520 0.6805 0.1119 0.084 Uiso 1 1 calc R . .
C5 C 0.968(3) 0.5947(15) 0.2162(16) 0.084(6) Uani 1 1 d . . .
H5 H 0.9323 0.5330 0.1908 0.100 Uiso 1 1 calc R . .
C6 C 1.068(3) 0.5986(19) 0.2973(17) 0.094(7) Uani 1 1 d . . .
H6 H 1.1106 0.5396 0.3257 0.113 Uiso 1 1 calc R . .
C7 C 1.108(3) 0.6921(18) 0.3392(14) 0.087(6) Uani 1 1 d . . .
H7 H 1.1692 0.6954 0.3974 0.104 Uiso 1 1 calc R . .
C8 C 1.055(2) 0.7773(13) 0.2936(11) 0.062(4) Uani 1 1 d . . .
C9 C 0.811(2) 1.1167(12) 0.0654(10) 0.052(4) Uani 1 1 d . . .
C10 C 0.887(2) 1.1892(13) 0.1246(11) 0.066(5) Uani 1 1 d . . .
H10 H 0.9516 1.1711 0.1796 0.079 Uiso 1 1 calc R . .
C11 C 0.866(3) 1.2886(14) 0.1005(11) 0.069(5) Uani 1 1 d . . .
H11 H 0.9137 1.3382 0.1404 0.083 Uiso 1 1 calc R . .
C12 C 0.772(2) 1.3166(13) 0.0157(11) 0.063(4) Uani 1 1 d . . .
H12 H 0.7607 1.3835 -0.0021 0.076 Uiso 1 1 calc R . .
C13 C 0.700(2) 1.2408(12) -0.0388(9) 0.053(4) Uani 1 1 d . . .
C14 C 0.718(2) 1.1411(13) -0.0173(10) 0.054(4) Uani 1 1 d . . .
H14 H 0.6696 1.0917 -0.0571 0.065 Uiso 1 1 calc R . .


_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 C8 1.913(18) . ?
O1 N4 1.211(19) . ?
O2 N4 1.20(2) . ?
N1 N2 1.341(17) . ?
N1 C1 1.343(18) . ?
N1 C9 1.443(19) . ?
N2 N3 1.29(2) . ?
N3 C2 1.379(19) . ?
N4 C13 1.493(18) . ?
C1 C2 1.32(2) . ?
C2 C3 1.49(2) . ?
C3 C4 1.38(2) . ?
C3 C8 1.41(2) . ?
C4 C5 1.41(3) . ?
C5 C6 1.34(3) . ?
C6 C7 1.41(3) . ?
C7 C8 1.35(3) . ?
C9 C14 1.37(2) . ?
C9 C10 1.38(2) . ?
C10 C11 1.37(2) . ?
C11 C12 1.42(2) . ?
C12 C13 1.36(2) . ?
C13 C14 1.37(2) . ?

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
N2 N1 C1 108.7(12) . . ?
N2 N1 C9 119.8(11) . . ?
C1 N1 C9 131.4(12) . . ?
N3 N2 N1 107.8(12) . . ?
N2 N3 C2 109.2(14) . . ?
O2 N4 O1 123.7(15) . . ?
O2 N4 C13 117.2(16) . . ?
O1 N4 C13 119.1(14) . . ?
C2 C1 N1 107.7(13) . . ?
C1 C2 N3 106.5(14) . . ?
C1 C2 C3 136.4(14) . . ?
N3 C2 C3 117.1(14) . . ?
C4 C3 C8 115.5(15) . . ?
C4 C3 C2 119.0(14) . . ?
C8 C3 C2 125.5(15) . . ?
C3 C4 C5 121.9(18) . . ?
C6 C5 C4 120(2) . . ?
C5 C6 C7 119.8(19) . . ?
C8 C7 C6 119.1(19) . . ?
C7 C8 C3 123.5(18) . . ?
C7 C8 Br1 115.0(14) . . ?
C3 C8 Br1 121.5(12) . . ?
C14 C9 C10 122.0(15) . . ?
C14 C9 N1 119.0(13) . . ?
C10 C9 N1 119.0(13) . . ?
C11 C10 C9 118.6(14) . . ?
C10 C11 C12 120.9(15) . . ?
C13 C12 C11 117.0(15) . . ?
C12 C13 C14 123.9(14) . . ?
C12 C13 N4 119.1(14) . . ?
C14 C13 N4 116.9(14) . . ?
C13 C14 C9 117.5(15) . . ?

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
C1 N1 N2 N3 0(2) . . . . ?
C9 N1 N2 N3 -178.7(14) . . . . ?
N1 N2 N3 C2 -1(2) . . . . ?
N2 N1 C1 C2 1.3(19) . . . . ?
C9 N1 C1 C2 179.3(15) . . . . ?
N1 C1 C2 N3 -2(2) . . . . ?
N1 C1 C2 C3 178.1(18) . . . . ?
N2 N3 C2 C1 1(2) . . . . ?
N2 N3 C2 C3 -178.4(15) . . . . ?
C1 C2 C3 C4 -177(2) . . . . ?
N3 C2 C3 C4 2(2) . . . . ?
C1 C2 C3 C8 3(3) . . . . ?
N3 C2 C3 C8 -177.6(17) . . . . ?
C8 C3 C4 C5 0(3) . . . . ?
C2 C3 C4 C5 -179.7(17) . . . . ?
C3 C4 C5 C6 -3(3) . . . . ?
C4 C5 C6 C7 5(3) . . . . ?
C5 C6 C7 C8 -5(3) . . . . ?
C6 C7 C8 C3 2(3) . . . . ?
C6 C7 C8 Br1 -177.6(16) . . . . ?
C4 C3 C8 C7 0(3) . . . . ?
C2 C3 C8 C7 -179.7(18) . . . . ?
C4 C3 C8 Br1 179.6(13) . . . . ?
C2 C3 C8 Br1 0(2) . . . . ?
N2 N1 C9 C14 -2(2) . . . . ?
C1 N1 C9 C14 -179.9(16) . . . . ?
N2 N1 C9 C10 179.9(16) . . . . ?
C1 N1 C9 C10 2(3) . . . . ?
C14 C9 C10 C11 1(3) . . . . ?
N1 C9 C10 C11 179.4(16) . . . . ?
C9 C10 C11 C12 -2(3) . . . . ?
C10 C11 C12 C13 2(3) . . . . ?
C11 C12 C13 C14 -2(3) . . . . ?
C11 C12 C13 N4 179.8(15) . . . . ?
O2 N4 C13 C12 -9(2) . . . . ?
O1 N4 C13 C12 170.6(17) . . . . ?
O2 N4 C13 C14 172.2(16) . . . . ?
O1 N4 C13 C14 -8(2) . . . . ?
C12 C13 C14 C9 2(3) . . . . ?
N4 C13 C14 C9 179.9(14) . . . . ?
C10 C9 C14 C13 -1(3) . . . . ?
N1 C9 C14 C13 -179.3(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 N3 0.93 2.71 3.61(2) 161.3 4_676
C10 H10 O2 0.93 2.67 3.57(2) 165.0 4_686

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         2.445
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.188

#===END

data_14
_database_code_depnum_ccdc_archive 'CCDC 679562'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Br N4 O2'
_chemical_formula_sum            'C14 H9 Br N4 O2'
_chemical_formula_weight         345.16

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4402(6)
_cell_length_b                   12.4535(10)
_cell_length_c                   14.6016(12)
_cell_angle_alpha                91.2720(10)
_cell_angle_beta                 98.9940(10)
_cell_angle_gamma                96.3090(10)
_cell_volume                     1327.14(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3070
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      22.83

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    3.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4270
_exptl_absorpt_correction_T_max  0.7673
_exptl_absorpt_process_details   'bruker sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12926
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4654
_reflns_number_gt                3565
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0437P)²+0.1079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4654
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.92978(5) 0.14785(3) 1.41562(2) 0.06378(13) Uani 1 1 d . . .
N1 N 0.7855(3) 0.06145(17) 0.90669(15) 0.0416(5) Uani 1 1 d . . .
N2 N 0.8915(4) 0.15037(19) 0.94790(17) 0.0542(7) Uani 1 1 d . . .
N3 N 0.8994(4) 0.1414(2) 1.03725(17) 0.0555(7) Uani 1 1 d . . .
N4 N 0.5601(3) -0.1641(2) 0.62607(18) 0.0527(6) Uani 1 1 d . . .
O1 O 0.5054(3) -0.23470(17) 0.67432(16) 0.0698(6) Uani 1 1 d . . .
O2 O 0.5451(4) -0.1736(2) 0.54156(17) 0.0807(7) Uani 1 1 d . . .
C1 C 0.7270(4) -0.0028(2) 0.97081(19) 0.0447(7) Uani 1 1 d . . .
H1 H 0.6524 -0.0683 0.9604 0.054 Uiso 1 1 calc R . .
C2 C 0.7991(4) 0.0474(2) 1.05452(19) 0.0424(7) Uani 1 1 d . . .
C3 C 0.7835(4) 0.0136(2) 1.14885(19) 0.0424(7) Uani 1 1 d . . .
C4 C 0.7112(4) -0.0917(2) 1.1636(2) 0.0530(8) Uani 1 1 d . . .
H4 H 0.6687 -0.1399 1.1134 0.064 Uiso 1 1 calc R . .
C5 C 0.7028(4) -0.1241(3) 1.2530(2) 0.0583(8) Uani 1 1 d . . .
H5 H 0.6532 -0.1942 1.2622 0.070 Uiso 1 1 calc R . .
C6 C 0.7667(4) -0.0545(3) 1.3287(2) 0.0569(8) Uani 1 1 d . . .
H6 H 0.7622 -0.0773 1.3886 0.068 Uiso 1 1 calc R . .
C7 C 0.8371(4) 0.0490(2) 1.31376(19) 0.0482(7) Uani 1 1 d . . .
C8 C 0.8457(4) 0.0843(2) 1.22476(19) 0.0461(7) Uani 1 1 d . . .
H8 H 0.8929 0.1550 1.2161 0.055 Uiso 1 1 calc R . .
C9 C 0.7548(4) 0.0469(2) 0.80784(18) 0.0400(6) Uani 1 1 d . . .
C10 C 0.8066(4) 0.1312(2) 0.7547(2) 0.0504(7) Uani 1 1 d . . .
H10 H 0.8587 0.1973 0.7832 0.060 Uiso 1 1 calc R . .
C11 C 0.7813(4) 0.1180(2) 0.6590(2) 0.0549(8) Uani 1 1 d . . .
H11 H 0.8188 0.1748 0.6235 0.066 Uiso 1 1 calc R . .
C12 C 0.7011(4) 0.0214(2) 0.6163(2) 0.0488(7) Uani 1 1 d . . .
H12 H 0.6830 0.0117 0.5521 0.059 Uiso 1 1 calc R . .
C13 C 0.6484(4) -0.0603(2) 0.67122(19) 0.0411(6) Uani 1 1 d . . .
C14 C 0.6732(4) -0.0511(2) 0.76674(19) 0.0433(7) Uani 1 1 d . . .
H14 H 0.6366 -0.1084 0.8020 0.052 Uiso 1 1 calc R . .
Br1' Br 0.15469(5) 0.34673(3) 0.17677(2) 0.05838(12) Uani 1 1 d . . .
O1' O 0.4704(3) 0.75528(18) 0.91475(17) 0.0750(7) Uani 1 1 d . . .
O2' O 0.4251(4) 0.6924(2) 1.04611(17) 0.0841(8) Uani 1 1 d . . .
N1' N 0.2094(3) 0.45830(18) 0.67869(14) 0.0402(5) Uani 1 1 d . . .
N2' N 0.1364(4) 0.35989(19) 0.63845(17) 0.0540(7) Uani 1 1 d . . .
N3' N 0.1432(4) 0.36546(19) 0.55021(17) 0.0544(7) Uani 1 1 d . . .
N4' N 0.4116(4) 0.6848(2) 0.96165(19) 0.0555(7) Uani 1 1 d . . .
C1' C 0.2621(4) 0.5246(2) 0.61428(18) 0.0441(7) Uani 1 1 d . . .
H1' H 0.3157 0.5958 0.6237 0.053 Uiso 1 1 calc R . .
C2' C 0.2211(4) 0.4662(2) 0.53211(18) 0.0412(6) Uani 1 1 d . . .
C3' C 0.2521(4) 0.4954(2) 0.43892(19) 0.0421(6) Uani 1 1 d . . .
C4' C 0.3368(4) 0.5970(2) 0.4237(2) 0.0491(7) Uani 1 1 d . . .
H4' H 0.3724 0.6475 0.4729 0.059 Uiso 1 1 calc R . .
C5' C 0.3684(4) 0.6234(3) 0.3361(2) 0.0549(8) Uani 1 1 d . . .
H5' H 0.4266 0.6915 0.3270 0.066 Uiso 1 1 calc R . .
C6' C 0.3154(4) 0.5509(3) 0.2614(2) 0.0514(8) Uani 1 1 d . . .
H6' H 0.3354 0.5693 0.2022 0.062 Uiso 1 1 calc R . .
C7' C 0.2317(4) 0.4501(2) 0.27730(19) 0.0445(7) Uani 1 1 d . . .
C8' C 0.2000(4) 0.4213(2) 0.36454(18) 0.0431(7) Uani 1 1 d . . .
H8' H 0.1442 0.3526 0.3735 0.052 Uiso 1 1 calc R . .
C9' C 0.2234(4) 0.4759(2) 0.77687(18) 0.0408(6) Uani 1 1 d . . .
C10' C 0.1478(4) 0.3952(2) 0.8276(2) 0.0542(8) Uani 1 1 d . . .
H10' H 0.0902 0.3309 0.7979 0.065 Uiso 1 1 calc R . .
C11' C 0.1575(5) 0.4100(3) 0.9222(2) 0.0616(9) Uani 1 1 d . . .
H11' H 0.1064 0.3558 0.9563 0.074 Uiso 1 1 calc R . .
C12' C 0.2433(4) 0.5054(3) 0.9662(2) 0.0552(8) Uani 1 1 d . . .
H12' H 0.2498 0.5166 1.0298 0.066 Uiso 1 1 calc R . .
C13' C 0.3182(4) 0.5829(2) 0.91445(19) 0.0436(7) Uani 1 1 d . . .
C14' C 0.3108(4) 0.5717(2) 0.81978(19) 0.0426(7) Uani 1 1 d . . .
H14' H 0.3623 0.6263 0.7862 0.051 Uiso 1 1 calc R . .


_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 C7 1.901(3) . ?
N1 C1 1.338(3) . ?
N1 N2 1.357(3) . ?
N1 C9 1.430(3) . ?
N2 N3 1.305(3) . ?
N3 C2 1.368(4) . ?
N4 O1 1.214(3) . ?
N4 O2 1.223(3) . ?
N4 C13 1.475(4) . ?
C1 C2 1.364(4) . ?
C2 C3 1.467(4) . ?
C3 C8 1.387(4) . ?
C3 C4 1.396(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.379(4) . ?
C6 C7 1.373(4) . ?
C7 C8 1.390(4) . ?
C9 C10 1.376(4) . ?
C9 C14 1.381(4) . ?
C10 C11 1.384(4) . ?
C11 C12 1.373(4) . ?
C12 C13 1.370(4) . ?
C13 C14 1.379(4) . ?
Br1' C7' 1.906(3) . ?
O1' N4' 1.211(3) . ?
O2' N4' 1.222(3) . ?
N1' C1' 1.341(3) . ?
N1' N2' 1.365(3) . ?
N1' C9' 1.431(3) . ?
N2' N3' 1.300(3) . ?
N3' C2' 1.372(3) . ?
N4' C13' 1.479(4) . ?
C1' C2' 1.364(4) . ?
C2' C3' 1.462(4) . ?
C3' C8' 1.388(4) . ?
C3' C4' 1.390(4) . ?
C4' C5' 1.377(4) . ?
C5' C6' 1.380(4) . ?
C6' C7' 1.379(4) . ?
C7' C8' 1.380(4) . ?
C9' C14' 1.381(4) . ?
C9' C10' 1.383(4) . ?
C10' C11' 1.379(4) . ?
C11' C12' 1.379(4) . ?
C12' C13' 1.363(4) . ?
C13' C14' 1.378(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
C1 N1 N2 110.3(2) . . ?
C1 N1 C9 129.7(2) . . ?
N2 N1 C9 120.0(2) . . ?
N3 N2 N1 106.9(2) . . ?
N2 N3 C2 109.6(2) . . ?
O1 N4 O2 123.7(3) . . ?
O1 N4 C13 118.5(2) . . ?
O2 N4 C13 117.7(3) . . ?
N1 C1 C2 105.9(2) . . ?
C1 C2 N3 107.3(2) . . ?
C1 C2 C3 130.1(3) . . ?
N3 C2 C3 122.6(2) . . ?
C8 C3 C4 119.0(3) . . ?
C8 C3 C2 120.7(2) . . ?
C4 C3 C2 120.2(3) . . ?
C5 C4 C3 119.9(3) . . ?
C6 C5 C4 121.2(3) . . ?
C7 C6 C5 118.6(3) . . ?
C6 C7 C8 121.5(3) . . ?
C6 C7 Br1 120.4(2) . . ?
C8 C7 Br1 118.1(2) . . ?
C3 C8 C7 119.7(3) . . ?
C10 C9 C14 120.8(3) . . ?
C10 C9 N1 119.4(2) . . ?
C14 C9 N1 119.9(2) . . ?
C9 C10 C11 120.2(3) . . ?
C12 C11 C10 120.2(3) . . ?
C13 C12 C11 118.0(3) . . ?
C12 C13 C14 123.6(3) . . ?
C12 C13 N4 118.5(2) . . ?
C14 C13 N4 117.9(3) . . ?
C13 C14 C9 117.1(3) . . ?
C1' N1' N2' 110.1(2) . . ?
C1' N1' C9' 130.2(2) . . ?
N2' N1' C9' 119.7(2) . . ?
N3' N2' N1' 106.9(2) . . ?
N2' N3' C2' 109.7(2) . . ?
O1' N4' O2' 124.0(3) . . ?
O1' N4' C13' 118.4(2) . . ?
O2' N4' C13' 117.6(3) . . ?
N1' C1' C2' 106.0(2) . . ?
C1' C2' N3' 107.4(2) . . ?
C1' C2' C3' 130.5(2) . . ?
N3' C2' C3' 122.1(2) . . ?
C8' C3' C4' 119.0(3) . . ?
C8' C3' C2' 120.5(2) . . ?
C4' C3' C2' 120.5(3) . . ?
C5' C4' C3' 120.3(3) . . ?
C4' C5' C6' 121.2(3) . . ?
C7' C6' C5' 118.0(3) . . ?
C6' C7' C8' 121.9(3) . . ?
C6' C7' Br1' 119.8(2) . . ?
C8' C7' Br1' 118.2(2) . . ?
C7' C8' C3' 119.6(3) . . ?
C14' C9' C10' 120.9(3) . . ?
C14' C9' N1' 120.4(2) . . ?
C10' C9' N1' 118.7(2) . . ?
C11' C10' C9' 120.1(3) . . ?
C10' C11' C12' 119.8(3) . . ?
C13' C12' C11' 118.7(3) . . ?
C12' C13' C14' 123.4(3) . . ?
C12' C13' N4' 118.7(3) . . ?
C14' C13' N4' 117.9(3) . . ?
C13' C14' C9' 117.1(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
C1 N1 N2 N3 0.2(3) . . . . ?
C9 N1 N2 N3 -178.5(2) . . . . ?
N1 N2 N3 C2 -0.1(3) . . . . ?
N2 N1 C1 C2 -0.2(3) . . . . ?
C9 N1 C1 C2 178.3(3) . . . . ?
N1 C1 C2 N3 0.1(3) . . . . ?
N1 C1 C2 C3 -178.9(3) . . . . ?
N2 N3 C2 C1 0.0(3) . . . . ?
N2 N3 C2 C3 179.1(3) . . . . ?
C1 C2 C3 C8 -170.5(3) . . . . ?
N3 C2 C3 C8 10.7(4) . . . . ?
C1 C2 C3 C4 11.7(5) . . . . ?
N3 C2 C3 C4 -167.2(3) . . . . ?
C8 C3 C4 C5 -0.2(4) . . . . ?
C2 C3 C4 C5 177.8(3) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C4 C5 C6 C7 0.9(5) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C5 C6 C7 Br1 -179.2(2) . . . . ?
C4 C3 C8 C7 0.8(4) . . . . ?
C2 C3 C8 C7 -177.1(3) . . . . ?
C6 C7 C8 C3 -0.6(4) . . . . ?
Br1 C7 C8 C3 178.4(2) . . . . ?
C1 N1 C9 C10 170.6(3) . . . . ?
N2 N1 C9 C10 -11.0(4) . . . . ?
C1 N1 C9 C14 -9.1(4) . . . . ?
N2 N1 C9 C14 169.2(3) . . . . ?
C14 C9 C10 C11 -1.5(4) . . . . ?
N1 C9 C10 C11 178.7(3) . . . . ?
C9 C10 C11 C12 1.3(5) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C11 C12 C13 N4 179.3(3) . . . . ?
O1 N4 C13 C12 -176.5(3) . . . . ?
O2 N4 C13 C12 3.0(4) . . . . ?
O1 N4 C13 C14 3.5(4) . . . . ?
O2 N4 C13 C14 -177.0(3) . . . . ?
C12 C13 C14 C9 0.5(4) . . . . ?
N4 C13 C14 C9 -179.5(2) . . . . ?
C10 C9 C14 C13 0.7(4) . . . . ?
N1 C9 C14 C13 -179.6(2) . . . . ?
C1' N1' N2' N3' -0.3(3) . . . . ?
C9' N1' N2' N3' -178.8(2) . . . . ?
N1' N2' N3' C2' 0.5(3) . . . . ?
N2' N1' C1' C2' 0.0(3) . . . . ?
C9' N1' C1' C2' 178.3(2) . . . . ?
N1' C1' C2' N3' 0.3(3) . . . . ?
N1' C1' C2' C3' -178.2(3) . . . . ?
N2' N3' C2' C1' -0.5(3) . . . . ?
N2' N3' C2' C3' 178.1(3) . . . . ?
C1' C2' C3' C8' 179.2(3) . . . . ?
N3' C2' C3' C8' 1.0(4) . . . . ?
C1' C2' C3' C4' 0.3(5) . . . . ?
N3' C2' C3' C4' -177.9(3) . . . . ?
C8' C3' C4' C5' 0.0(4) . . . . ?
C2' C3' C4' C5' 178.9(3) . . . . ?
C3' C4' C5' C6' 0.8(5) . . . . ?
C4' C5' C6' C7' -0.9(5) . . . . ?
C5' C6' C7' C8' 0.3(4) . . . . ?
C5' C6' C7' Br1' 179.8(2) . . . . ?
C6' C7' C8' C3' 0.5(4) . . . . ?
Br1' C7' C8' C3' -179.0(2) . . . . ?
C4' C3' C8' C7' -0.6(4) . . . . ?
C2' C3' C8' C7' -179.5(2) . . . . ?
C1' N1' C9' C14' -3.7(4) . . . . ?
N2' N1' C9' C14' 174.5(3) . . . . ?
C1' N1' C9' C10' 176.3(3) . . . . ?
N2' N1' C9' C10' -5.6(4) . . . . ?
C14' C9' C10' C11' 0.5(5) . . . . ?
N1' C9' C10' C11' -179.4(3) . . . . ?
C9' C10' C11' C12' -0.1(5) . . . . ?
C10' C11' C12' C13' -0.6(5) . . . . ?
C11' C12' C13' C14' 0.9(5) . . . . ?
C11' C12' C13' N4' -179.5(3) . . . . ?
O1' N4' C13' C12' -176.6(3) . . . . ?
O2' N4' C13' C12' 3.6(4) . . . . ?
O1' N4' C13' C14' 3.0(4) . . . . ?
O2' N4' C13' C14' -176.8(3) . . . . ?
C12' C13' C14' C9' -0.6(4) . . . . ?
N4' C13' C14' C9' 179.8(2) . . . . ?
C10' C9' C14' C13' -0.2(4) . . . . ?
N1' C9' C14' C13' 179.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8' H8' Br1 0.93 2.98 3.908(3) 172.1 1_454
C8 H8 Br1' 0.93 3.04 3.926(3) 160.8 1_656
C14' H14' O1 0.93 2.66 3.584(4) 173.4 1_565
C4' H4' O2 0.93 2.55 3.391(4) 150.9 1_565
C1' H1' O1 0.93 2.44 3.351(4) 167.1 1_565
C4 H4 O2' 0.93 2.67 3.478(4) 145.8 1_545
C1 H1 O1' 0.93 2.47 3.395(3) 172.8 1_545

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.058

#===END

data_15
_database_code_depnum_ccdc_archive 'CCDC 679563'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Br N4 O2'
_chemical_formula_sum            'C14 H9 Br N4 O2'
_chemical_formula_weight         345.16

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           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                   8.667(3)
_cell_length_b                   5.2323(18)
_cell_length_c                   30.304(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.248(6)
_cell_angle_gamma                90.00
_cell_volume                     1366.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1536
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      22.18

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    3.019
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.4013
_exptl_absorpt_correction_T_max  0.9149
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6524
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2403
_reflns_number_gt                1718
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0536P)²+0.8225P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    REFALL
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2403
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_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 0.41429(6) 0.60503(13) 0.198319(15) 0.1014(3) Uani 1 1 d . . .
O1 O 0.5458(3) -0.0305(5) 0.55246(9) 0.0634(7) Uani 1 1 d . . .
O2 O 0.6556(3) 0.0169(6) 0.61895(9) 0.0702(8) Uani 1 1 d . . .
N1 N 0.7654(3) 0.6420(5) 0.46216(9) 0.0449(7) Uani 1 1 d . . .
N2 N 0.8255(4) 0.8674(5) 0.45012(11) 0.0584(8) Uani 1 1 d . . .
N3 N 0.7884(4) 0.8931(6) 0.40738(10) 0.0590(8) Uani 1 1 d . . .
N4 N 0.6364(3) 0.0780(5) 0.58010(10) 0.0507(7) Uani 1 1 d . . .
C1 C 0.6902(4) 0.5279(7) 0.42642(11) 0.0453(8) Uani 1 1 d . . .
C2 C 0.7042(4) 0.6861(6) 0.39176(12) 0.0471(8) Uani 1 1 d . . .
C3 C 0.6396(4) 0.6623(6) 0.34477(11) 0.0477(8) Uani 1 1 d . . .
C4 C 0.5360(6) 0.4728(9) 0.33145(14) 0.0710(13) Uani 1 1 d . . .
C5 C 0.4709(6) 0.4555(11) 0.28808(15) 0.0783(13) Uani 1 1 d . . .
C6 C 0.5083(5) 0.6278(9) 0.25769(13) 0.0637(11) Uani 1 1 d . . .
C7 C 0.6127(6) 0.8163(10) 0.26996(16) 0.0788(14) Uani 1 1 d . . .
C8 C 0.6777(6) 0.8330(9) 0.31329(15) 0.0706(12) Uani 1 1 d . . .
C9 C 0.7879(4) 0.5634(6) 0.50744(11) 0.0438(8) Uani 1 1 d . . .
C10 C 0.8956(4) 0.6891(7) 0.53709(12) 0.0491(9) Uani 1 1 d . . .
C11 C 0.9149(4) 0.6146(7) 0.58101(13) 0.0543(10) Uani 1 1 d . . .
C12 C 0.8314(4) 0.4153(7) 0.59597(13) 0.0513(9) Uani 1 1 d . . .
C13 C 0.7270(4) 0.2922(6) 0.56537(11) 0.0430(8) Uani 1 1 d . . .
C14 C 0.7023(4) 0.3623(6) 0.52129(11) 0.0416(8) Uani 1 1 d . . .
H1 H 0.644(4) 0.376(6) 0.4279(10) 0.041(9) Uiso 1 1 d . . .
H4 H 0.514(5) 0.367(7) 0.3514(14) 0.068(13) Uiso 1 1 d . . .
H5 H 0.408(7) 0.319(11) 0.2822(19) 0.13(2) Uiso 1 1 d . . .
H7 H 0.638(5) 0.927(9) 0.2500(16) 0.089(16) Uiso 1 1 d . . .
H8 H 0.740(4) 0.955(7) 0.3218(12) 0.055(11) Uiso 1 1 d . . .
H10 H 0.948(4) 0.830(7) 0.5272(11) 0.049(10) Uiso 1 1 d . . .
H11 H 0.986(4) 0.699(7) 0.5991(12) 0.055(10) Uiso 1 1 d . . .
H12 H 0.844(4) 0.361(6) 0.6247(13) 0.055(10) Uiso 1 1 d . . .
H14 H 0.633(4) 0.276(6) 0.5017(11) 0.049(9) Uiso 1 1 d . . .


_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 C6 1.896(4) . ?
O1 N4 1.224(4) . ?
O2 N4 1.214(4) . ?
N1 C1 1.342(4) . ?
N1 N2 1.356(4) . ?
N1 C9 1.425(4) . ?
N2 N3 1.307(4) . ?
N3 C2 1.362(4) . ?
N4 C13 1.465(4) . ?
C1 C2 1.353(5) . ?
C2 C3 1.478(5) . ?
C3 C4 1.369(5) . ?
C3 C8 1.373(5) . ?
C4 C5 1.376(6) . ?
C5 C6 1.353(6) . ?
C6 C7 1.363(6) . ?
C7 C8 1.374(6) . ?
C9 C14 1.379(5) . ?
C9 C10 1.389(5) . ?
C10 C11 1.380(5) . ?
C11 C12 1.374(5) . ?
C12 C13 1.382(5) . ?
C13 C14 1.379(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
C1 N1 N2 109.7(3) . . ?
C1 N1 C9 130.7(3) . . ?
N2 N1 C9 119.6(3) . . ?
N3 N2 N1 107.2(3) . . ?
N2 N3 C2 109.1(3) . . ?
O2 N4 O1 123.5(3) . . ?
O2 N4 C13 118.4(3) . . ?
O1 N4 C13 118.1(3) . . ?
N1 C1 C2 106.1(3) . . ?
C1 C2 N3 107.9(3) . . ?
C1 C2 C3 129.8(3) . . ?
N3 C2 C3 122.3(3) . . ?
C4 C3 C8 117.8(4) . . ?
C4 C3 C2 120.8(3) . . ?
C8 C3 C2 121.4(3) . . ?
C3 C4 C5 121.1(4) . . ?
C6 C5 C4 120.2(4) . . ?
C5 C6 C7 119.9(4) . . ?
C5 C6 Br1 119.6(3) . . ?
C7 C6 Br1 120.5(3) . . ?
C6 C7 C8 119.9(4) . . ?
C3 C8 C7 121.2(4) . . ?
C14 C9 C10 120.7(3) . . ?
C14 C9 N1 119.4(3) . . ?
C10 C9 N1 119.9(3) . . ?
C11 C10 C9 119.5(4) . . ?
C12 C11 C10 121.3(4) . . ?
C11 C12 C13 117.5(4) . . ?
C14 C13 C12 123.1(3) . . ?
C14 C13 N4 117.8(3) . . ?
C12 C13 N4 119.0(3) . . ?
C9 C14 C13 117.8(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
C1 N1 N2 N3 -0.1(4) . . . . ?
C9 N1 N2 N3 -179.9(3) . . . . ?
N1 N2 N3 C2 0.2(4) . . . . ?
N2 N1 C1 C2 0.0(4) . . . . ?
C9 N1 C1 C2 179.7(3) . . . . ?
N1 C1 C2 N3 0.2(4) . . . . ?
N1 C1 C2 C3 -177.5(3) . . . . ?
N2 N3 C2 C1 -0.2(4) . . . . ?
N2 N3 C2 C3 177.6(3) . . . . ?
C1 C2 C3 C4 7.6(6) . . . . ?
N3 C2 C3 C4 -169.8(4) . . . . ?
C1 C2 C3 C8 -174.3(4) . . . . ?
N3 C2 C3 C8 8.3(6) . . . . ?
C8 C3 C4 C5 -0.7(7) . . . . ?
C2 C3 C4 C5 177.5(4) . . . . ?
C3 C4 C5 C6 -0.2(8) . . . . ?
C4 C5 C6 C7 1.1(7) . . . . ?
C4 C5 C6 Br1 -178.8(4) . . . . ?
C5 C6 C7 C8 -1.0(7) . . . . ?
Br1 C6 C7 C8 178.8(4) . . . . ?
C4 C3 C8 C7 0.8(7) . . . . ?
C2 C3 C8 C7 -177.4(4) . . . . ?
C6 C7 C8 C3 0.1(7) . . . . ?
C1 N1 C9 C14 -12.5(5) . . . . ?
N2 N1 C9 C14 167.2(3) . . . . ?
C1 N1 C9 C10 167.3(3) . . . . ?
N2 N1 C9 C10 -12.9(5) . . . . ?
C14 C9 C10 C11 -1.2(5) . . . . ?
N1 C9 C10 C11 179.0(3) . . . . ?
C9 C10 C11 C12 1.1(6) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C11 C12 C13 N4 179.7(3) . . . . ?
O2 N4 C13 C14 -179.0(3) . . . . ?
O1 N4 C13 C14 1.3(4) . . . . ?
O2 N4 C13 C12 0.5(5) . . . . ?
O1 N4 C13 C12 -179.2(3) . . . . ?
C10 C9 C14 C13 0.3(5) . . . . ?
N1 C9 C14 C13 -179.8(3) . . . . ?
C12 C13 C14 C9 0.7(5) . . . . ?
N4 C13 C14 C9 -179.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 N2 0.93(4) 2.56(4) 3.342(5) 142(3) 3_776
C4 H4 O2 0.86(4) 2.70(4) 3.482(5) 153(3) 3_656
C14 H14 O1 0.92(3) 2.49(3) 3.404(4) 177(3) 3_656
C1 H1 O1 0.89(3) 2.56(3) 3.413(5) 161(3) 3_656

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.057

#===END

data_16
_database_code_depnum_ccdc_archive 'CCDC 679564'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 N4 O2'
_chemical_formula_sum            'C14 H10 N4 O2'
_chemical_formula_weight         266.26

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.757(2)
_cell_length_b                   7.198(3)
_cell_length_c                   14.862(6)
_cell_angle_alpha                101.081(6)
_cell_angle_beta                 99.217(6)
_cell_angle_gamma                90.859(6)
_cell_volume                     595.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2295
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.74

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9315
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_process_details   'bruker sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4652
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2296
_reflns_number_gt                2006
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'

_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)+(0.0543P)²+0.1231P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2296
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_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
O1 O 0.0476(2) -0.2112(2) 0.00540(8) 0.0689(4) Uani 1 1 d . . .
O2 O -0.2953(2) -0.1897(2) 0.04544(8) 0.0776(4) Uani 1 1 d . . .
N1 N 0.32113(18) 0.18190(15) 0.42594(7) 0.0320(3) Uani 1 1 d . . .
N2 N 0.55834(19) 0.19502(17) 0.45150(8) 0.0393(3) Uani 1 1 d . . .
N3 N 0.60249(19) 0.27687(17) 0.53911(8) 0.0391(3) Uani 1 1 d . . .
N4 N -0.0818(2) -0.16618(18) 0.06263(8) 0.0465(3) Uani 1 1 d . . .
C1 C 0.2148(2) 0.25638(18) 0.49866(9) 0.0329(3) Uani 1 1 d . . .
C2 C 0.3947(2) 0.31752(17) 0.57052(9) 0.0312(3) Uani 1 1 d . . .
C3 C 0.3868(2) 0.40877(17) 0.66732(8) 0.0312(3) Uani 1 1 d . . .
C4 C 0.5798(2) 0.40535(19) 0.73656(9) 0.0358(3) Uani 1 1 d . . .
C5 C 0.5715(3) 0.4882(2) 0.82794(10) 0.0413(3) Uani 1 1 d . . .
C6 C 0.3714(3) 0.5752(2) 0.85153(10) 0.0421(3) Uani 1 1 d . . .
C7 C 0.1791(2) 0.5797(2) 0.78347(10) 0.0403(3) Uani 1 1 d . . .
C8 C 0.1858(2) 0.49702(19) 0.69168(10) 0.0361(3) Uani 1 1 d . . .
C9 C 0.2188(2) 0.09372(17) 0.33377(8) 0.0308(3) Uani 1 1 d . . .
C10 C -0.0036(2) 0.00526(19) 0.31776(9) 0.0352(3) Uani 1 1 d . . .
C11 C -0.1025(2) -0.07915(19) 0.22806(9) 0.0361(3) Uani 1 1 d . . .
C12 C 0.0256(2) -0.07538(18) 0.15746(9) 0.0348(3) Uani 1 1 d . . .
C13 C 0.2481(2) 0.01044(19) 0.17242(9) 0.0373(3) Uani 1 1 d . . .
C14 C 0.3444(2) 0.09852(19) 0.26166(9) 0.0348(3) Uani 1 1 d . . .
H1 H 0.050(3) 0.2583(19) 0.4931(10) 0.038(4) Uiso 1 1 d . . .
H4 H 0.722(3) 0.344(2) 0.7209(10) 0.038(4) Uiso 1 1 d . . .
H5 H 0.708(3) 0.486(2) 0.8741(12) 0.049(4) Uiso 1 1 d . . .
H6 H 0.361(3) 0.631(2) 0.9145(12) 0.052(4) Uiso 1 1 d . . .
H7 H 0.036(3) 0.643(2) 0.7998(11) 0.046(4) Uiso 1 1 d . . .
H8 H 0.049(3) 0.499(2) 0.6445(11) 0.039(4) Uiso 1 1 d . . .
H10 H -0.090(3) 0.001(2) 0.3681(11) 0.046(4) Uiso 1 1 d . . .
H11 H -0.257(3) -0.141(2) 0.2156(11) 0.045(4) Uiso 1 1 d . . .
H13 H 0.334(3) 0.012(2) 0.1211(11) 0.048(4) Uiso 1 1 d . . .
H14 H 0.498(3) 0.163(2) 0.2743(11) 0.043(4) Uiso 1 1 d . . .


_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 N4 1.2195(17) . ?
O2 N4 1.2172(18) . ?
N1 C1 1.3524(16) . ?
N1 N2 1.3542(16) . ?
N1 C9 1.4221(16) . ?
N2 N3 1.3045(16) . ?
N3 C2 1.3680(17) . ?
N4 C12 1.4663(18) . ?
C1 C2 1.3631(18) . ?
C2 C3 1.4704(18) . ?
C3 C4 1.3925(19) . ?
C3 C8 1.3931(18) . ?
C4 C5 1.383(2) . ?
C5 C6 1.382(2) . ?
C6 C7 1.380(2) . ?
C7 C8 1.386(2) . ?
C9 C10 1.3862(18) . ?
C9 C14 1.3905(18) . ?
C10 C11 1.3804(19) . ?
C11 C12 1.3795(19) . ?
C12 C13 1.380(2) . ?
C13 C14 1.3781(19) . ?

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
C1 N1 N2 110.54(10) . . ?
C1 N1 C9 129.40(11) . . ?
N2 N1 C9 120.03(10) . . ?
N3 N2 N1 107.05(10) . . ?
N2 N3 C2 109.30(11) . . ?
O2 N4 O1 123.90(13) . . ?
O2 N4 C12 117.94(12) . . ?
O1 N4 C12 118.15(13) . . ?
N1 C1 C2 104.96(11) . . ?
C1 C2 N3 108.14(11) . . ?
C1 C2 C3 129.73(12) . . ?
N3 C2 C3 122.12(11) . . ?
C4 C3 C8 118.91(12) . . ?
C4 C3 C2 120.23(12) . . ?
C8 C3 C2 120.86(12) . . ?
C5 C4 C3 120.39(13) . . ?
C6 C5 C4 120.34(13) . . ?
C7 C6 C5 119.78(13) . . ?
C6 C7 C8 120.29(13) . . ?
C7 C8 C3 120.30(13) . . ?
C10 C9 C14 121.49(12) . . ?
C10 C9 N1 119.35(11) . . ?
C14 C9 N1 119.16(11) . . ?
C11 C10 C9 119.06(12) . . ?
C12 C11 C10 118.75(13) . . ?
C11 C12 C13 122.86(12) . . ?
C11 C12 N4 118.04(12) . . ?
C13 C12 N4 119.11(12) . . ?
C14 C13 C12 118.35(12) . . ?
C13 C14 C9 119.46(12) . . ?

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
C1 N1 N2 N3 -0.10(14) . . . . ?
C9 N1 N2 N3 -178.47(10) . . . . ?
N1 N2 N3 C2 -0.18(14) . . . . ?
N2 N1 C1 C2 0.33(14) . . . . ?
C9 N1 C1 C2 178.50(12) . . . . ?
N1 C1 C2 N3 -0.43(14) . . . . ?
N1 C1 C2 C3 -179.28(12) . . . . ?
N2 N3 C2 C1 0.39(15) . . . . ?
N2 N3 C2 C3 179.34(11) . . . . ?
C1 C2 C3 C4 159.14(13) . . . . ?
N3 C2 C3 C4 -19.57(18) . . . . ?
C1 C2 C3 C8 -19.8(2) . . . . ?
N3 C2 C3 C8 161.51(12) . . . . ?
C8 C3 C4 C5 0.0(2) . . . . ?
C2 C3 C4 C5 -178.90(12) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C7 -0.1(2) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 C3 0.0(2) . . . . ?
C4 C3 C8 C7 0.0(2) . . . . ?
C2 C3 C8 C7 178.89(12) . . . . ?
C1 N1 C9 C10 -26.69(19) . . . . ?
N2 N1 C9 C10 151.33(12) . . . . ?
C1 N1 C9 C14 153.21(13) . . . . ?
N2 N1 C9 C14 -28.76(17) . . . . ?
C14 C9 C10 C11 -0.3(2) . . . . ?
N1 C9 C10 C11 179.64(11) . . . . ?
C9 C10 C11 C12 1.1(2) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C10 C11 C12 N4 179.83(12) . . . . ?
O2 N4 C12 C11 21.4(2) . . . . ?
O1 N4 C12 C11 -159.63(14) . . . . ?
O2 N4 C12 C13 -158.33(15) . . . . ?
O1 N4 C12 C13 20.7(2) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
N4 C12 C13 C14 178.67(12) . . . . ?
C12 C13 C14 C9 1.8(2) . . . . ?
C10 C9 C14 C13 -1.2(2) . . . . ?
N1 C9 C14 C13 178.85(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O1 0.956(17) 2.575(17) 3.342(2) 137.3(13) 1_566
C6 H6 O2 0.956(17) 2.660(17) 3.333(2) 127.7(12) 1_666

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.035

#===END

data_17
_database_code_depnum_ccdc_archive 'CCDC 679565'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Br N4 O2'
_chemical_formula_sum            'C14 H9 Br N4 O2'
_chemical_formula_weight         345.16

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   29.52(2)
_cell_length_b                   7.057(5)
_cell_length_c                   13.022(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.405(12)
_cell_angle_gamma                90.00
_cell_volume                     2690(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1795
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      23.17

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      red
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    3.066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2296
_exptl_absorpt_correction_T_max  0.5791
_exptl_absorpt_process_details   'bruker sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6468
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2377
_reflns_number_gt                1764
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'

_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)+(0.0577P)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_extinction_coef       ?
_refine_ls_number_reflns         2377
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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 0.43035(6) 0.18927(18) 0.27418(14) 0.0710(3) Uani 0.80 1 d P A 1
Br1' Br 0.4353(3) 0.2702(9) 0.2774(6) 0.103(2) Uani 0.20 1 d P A 2
O1 O 0.09916(9) 0.3109(4) 0.0456(2) 0.0885(8) Uani 1 1 d . . .
O2 O 0.14396(9) 0.3681(4) -0.06779(19) 0.0954(8) Uani 1 1 d . . .
N1 N 0.28795(7) 0.3591(3) 0.33043(15) 0.0413(5) Uani 1 1 d . . .
N2 N 0.28230(8) 0.3975(4) 0.42944(16) 0.0541(6) Uani 1 1 d . . .
N3 N 0.32249(8) 0.3865(4) 0.48381(16) 0.0577(6) Uani 1 1 d . . .
N4 N 0.13677(9) 0.3428(4) 0.0213(2) 0.0625(7) Uani 1 1 d . . .
C1 C 0.33215(9) 0.3245(4) 0.32299(19) 0.0451(7) Uani 1 1 d . . .
H1 H 0.3448 0.2952 0.2631 0.054 Uiso 1 1 calc R . .
C2 C 0.35481(9) 0.3409(4) 0.42078(19) 0.0442(6) Uani 1 1 d . . .
C3 C 0.40237(10) 0.3166(4) 0.4678(2) 0.0495(7) Uani 1 1 d . A .
C4 C 0.41215(12) 0.3527(5) 0.5733(2) 0.0776(11) Uani 1 1 d . . .
H4 H 0.3889 0.3934 0.6099 0.093 Uiso 1 1 calc R . .
C5 C 0.45566(15) 0.3295(6) 0.6251(3) 0.0989(14) Uani 1 1 d . . .
H5 H 0.4613 0.3552 0.6956 0.119 Uiso 1 1 calc R . .
C6 C 0.49054(13) 0.2691(6) 0.5733(3) 0.0886(12) Uani 1 1 d . . .
H6 H 0.5196 0.2504 0.6089 0.106 Uiso 1 1 calc R . .
C7 C 0.48234(12) 0.2365(5) 0.4692(3) 0.0727(10) Uani 1 1 d . A .
H7 H 0.5061 0.1997 0.4330 0.087 Uiso 1 1 calc R . .
C8 C 0.43861(11) 0.2584(4) 0.4175(2) 0.0556(7) Uani 1 1 d . . .
C9 C 0.24925(8) 0.3599(4) 0.25256(18) 0.0387(6) Uani 1 1 d . . .
C10 C 0.25549(9) 0.3902(4) 0.15035(18) 0.0455(6) Uani 1 1 d . . .
H10 H 0.2845 0.4127 0.1326 0.055 Uiso 1 1 calc R . .
C11 C 0.21827(9) 0.3867(4) 0.07559(19) 0.0477(7) Uani 1 1 d . . .
H11 H 0.2218 0.4076 0.0066 0.057 Uiso 1 1 calc R . .
C12 C 0.17576(9) 0.3522(4) 0.1033(2) 0.0471(7) Uani 1 1 d . . .
C13 C 0.16879(9) 0.3252(4) 0.2052(2) 0.0502(7) Uani 1 1 d . . .
H13 H 0.1396 0.3051 0.2226 0.060 Uiso 1 1 calc R . .
C14 C 0.20610(9) 0.3286(4) 0.2802(2) 0.0469(7) Uani 1 1 d . . .
H14 H 0.2024 0.3101 0.3494 0.056 Uiso 1 1 calc R . .


_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 C8 1.914(4) . ?
Br1' C8 1.817(8) . ?
O1 N4 1.214(4) . ?
O2 N4 1.219(3) . ?
N1 C1 1.343(3) . ?
N1 N2 1.349(3) . ?
N1 C9 1.426(3) . ?
N2 N3 1.303(3) . ?
N3 C2 1.374(3) . ?
N4 C12 1.467(4) . ?
C1 C2 1.365(4) . ?
C2 C3 1.467(4) . ?
C3 C8 1.387(4) . ?
C3 C4 1.391(4) . ?
C4 C5 1.381(5) . ?
C5 C6 1.369(6) . ?
C6 C7 1.366(5) . ?
C7 C8 1.385(5) . ?
C9 C10 1.384(3) . ?
C9 C14 1.385(4) . ?
C10 C11 1.371(4) . ?
C11 C12 1.371(4) . ?
C12 C13 1.382(4) . ?
C13 C14 1.375(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
C1 N1 N2 110.3(2) . . ?
C1 N1 C9 130.2(2) . . ?
N2 N1 C9 119.5(2) . . ?
N3 N2 N1 106.9(2) . . ?
N2 N3 C2 110.0(2) . . ?
O1 N4 O2 123.5(3) . . ?
O1 N4 C12 118.5(3) . . ?
O2 N4 C12 118.0(3) . . ?
N1 C1 C2 106.3(2) . . ?
C1 C2 N3 106.4(2) . . ?
C1 C2 C3 135.0(2) . . ?
N3 C2 C3 118.6(2) . . ?
C8 C3 C4 116.5(3) . . ?
C8 C3 C2 126.3(3) . . ?
C4 C3 C2 117.2(3) . . ?
C5 C4 C3 121.5(3) . . ?
C6 C5 C4 120.5(4) . . ?
C7 C6 C5 119.5(3) . . ?
C6 C7 C8 119.9(3) . . ?
C7 C8 C3 122.1(3) . . ?
C7 C8 Br1' 114.8(4) . . ?
C3 C8 Br1' 121.0(3) . . ?
C7 C8 Br1 116.0(3) . . ?
C3 C8 Br1 121.8(2) . . ?
Br1' C8 Br1 17.9(2) . . ?
C10 C9 C14 121.0(2) . . ?
C10 C9 N1 119.4(2) . . ?
C14 C9 N1 119.6(2) . . ?
C11 C10 C9 119.1(2) . . ?
C10 C11 C12 119.5(2) . . ?
C11 C12 C13 122.1(3) . . ?
C11 C12 N4 118.4(3) . . ?
C13 C12 N4 119.5(3) . . ?
C14 C13 C12 118.4(3) . . ?
C13 C14 C9 119.8(2) . . ?

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
C1 N1 N2 N3 -0.2(3) . . . . ?
C9 N1 N2 N3 179.7(2) . . . . ?
N1 N2 N3 C2 0.0(3) . . . . ?
N2 N1 C1 C2 0.3(3) . . . . ?
C9 N1 C1 C2 -179.6(3) . . . . ?
N1 C1 C2 N3 -0.3(3) . . . . ?
N1 C1 C2 C3 177.9(3) . . . . ?
N2 N3 C2 C1 0.1(3) . . . . ?
N2 N3 C2 C3 -178.4(2) . . . . ?
C1 C2 C3 C8 -2.7(5) . . . . ?
N3 C2 C3 C8 175.3(3) . . . . ?
C1 C2 C3 C4 178.3(3) . . . . ?
N3 C2 C3 C4 -3.7(4) . . . . ?
C8 C3 C4 C5 -0.7(5) . . . . ?
C2 C3 C4 C5 178.5(4) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
C4 C5 C6 C7 1.8(7) . . . . ?
C5 C6 C7 C8 -2.3(6) . . . . ?
C6 C7 C8 C3 1.3(5) . . . . ?
C6 C7 C8 Br1' 165.0(4) . . . . ?
C6 C7 C8 Br1 -175.2(3) . . . . ?
C4 C3 C8 C7 0.2(5) . . . . ?
C2 C3 C8 C7 -178.9(3) . . . . ?
C4 C3 C8 Br1' -162.5(3) . . . . ?
C2 C3 C8 Br1' 18.4(5) . . . . ?
C4 C3 C8 Br1 176.4(2) . . . . ?
C2 C3 C8 Br1 -2.6(4) . . . . ?
C1 N1 C9 C10 -23.7(4) . . . . ?
N2 N1 C9 C10 156.4(2) . . . . ?
C1 N1 C9 C14 155.8(3) . . . . ?
N2 N1 C9 C14 -24.2(4) . . . . ?
C14 C9 C10 C11 -0.8(4) . . . . ?
N1 C9 C10 C11 178.6(2) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C13 1.6(4) . . . . ?
C10 C11 C12 N4 -177.9(2) . . . . ?
O1 N4 C12 C11 179.5(3) . . . . ?
O2 N4 C12 C11 -0.7(4) . . . . ?
O1 N4 C12 C13 -0.1(4) . . . . ?
O2 N4 C12 C13 179.7(3) . . . . ?
C11 C12 C13 C14 -1.6(4) . . . . ?
N4 C12 C13 C14 177.9(2) . . . . ?
C12 C13 C14 C9 0.4(4) . . . . ?
C10 C9 C14 C13 0.8(4) . . . . ?
N1 C9 C14 C13 -178.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 N2 0.93 2.56 3.231(4) 129.5 6_565
C6 H6 O1 0.93 2.62 3.321(5) 132.3 8_556

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.068

#===END

data_18
_database_code_depnum_ccdc_archive 'CCDC 679566'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Br N4 O2'
_chemical_formula_sum            'C14 H9 Br N4 O2'
_chemical_formula_weight         345.16

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           Monoclinic
_symmetry_space_group_name_H-M   'p 21/c'

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

_cell_length_a                   7.5222(8)
_cell_length_b                   14.1697(15)
_cell_length_c                   13.0479(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.391(2)
_cell_angle_gamma                90.00
_cell_volume                     1390.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2112
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      23.88

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.88
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1800
_exptl_absorpt_correction_T_max  0.7888
_exptl_absorpt_process_details   'bruker sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7835
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2434
_reflns_number_gt                1859
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'

_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)+(0.0487P)²+0.6891P] 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_extinction_coef       ?
_refine_ls_number_reflns         2434
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1033
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.73011(7) 0.08413(3) 0.54878(3) 0.0877(2) Uani 1 1 d . . .
O1 O 0.9805(4) 0.95279(19) 0.6997(2) 0.0882(8) Uani 1 1 d . . .
O2 O 1.0472(3) 0.85450(18) 0.81932(18) 0.0741(7) Uani 1 1 d . . .
N1 N 0.7483(3) 0.57385(15) 0.48822(17) 0.0396(5) Uani 1 1 d . . .
N2 N 0.6644(4) 0.59087(17) 0.39803(18) 0.0534(7) Uani 1 1 d . . .
N3 N 0.6213(3) 0.50940(18) 0.35888(18) 0.0544(6) Uani 1 1 d . . .
N4 N 0.9887(4) 0.8730(2) 0.7343(2) 0.0594(7) Uani 1 1 d . . .
C1 C 0.7567(4) 0.48031(19) 0.5053(2) 0.0424(6) Uani 1 1 d . . .
H1 H 0.8071 0.4502 0.5618 0.051 Uiso 1 1 calc R . .
C2 C 0.6765(4) 0.43896(19) 0.4234(2) 0.0408(6) Uani 1 1 d . . .
C3 C 0.6475(3) 0.3385(2) 0.4005(2) 0.0432(7) Uani 1 1 d . . .
C4 C 0.5778(4) 0.3104(2) 0.3063(2) 0.0555(8) Uani 1 1 d . . .
H4 H 0.5481 0.3554 0.2573 0.067 Uiso 1 1 calc R . .
C5 C 0.5527(4) 0.2157(3) 0.2855(3) 0.0646(9) Uani 1 1 d . . .
H5 H 0.5058 0.1977 0.2223 0.078 Uiso 1 1 calc R . .
C6 C 0.5955(4) 0.1476(2) 0.3562(3) 0.0624(9) Uani 1 1 d . . .
H6 H 0.5785 0.0840 0.3417 0.075 Uiso 1 1 calc R . .
C7 C 0.6645(4) 0.1759(2) 0.4497(2) 0.0548(8) Uani 1 1 d . . .
C8 C 0.6896(4) 0.2702(2) 0.4726(2) 0.0465(7) Uani 1 1 d . . .
H8 H 0.7347 0.2877 0.5364 0.056 Uiso 1 1 calc R . .
C9 C 0.8093(3) 0.64938(18) 0.55042(19) 0.0388(6) Uani 1 1 d . . .
C10 C 0.8796(4) 0.6309(2) 0.6466(2) 0.0465(7) Uani 1 1 d . . .
H10 H 0.8867 0.5691 0.6705 0.056 Uiso 1 1 calc R . .
C11 C 0.9392(4) 0.7045(2) 0.7071(2) 0.0502(7) Uani 1 1 d . . .
H11 H 0.9880 0.6931 0.7716 0.060 Uiso 1 1 calc R . .
C12 C 0.9251(4) 0.7948(2) 0.6701(2) 0.0460(7) Uani 1 1 d . . .
C13 C 0.8557(4) 0.8144(2) 0.5744(2) 0.0518(7) Uani 1 1 d . . .
H13 H 0.8484 0.8763 0.5510 0.062 Uiso 1 1 calc R . .
C14 C 0.7978(4) 0.7414(2) 0.5145(2) 0.0471(7) Uani 1 1 d . . .
H14 H 0.7506 0.7533 0.4497 0.057 Uiso 1 1 calc R . .


_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 C7 1.897(3) . ?
O1 N4 1.218(4) . ?
O2 N4 1.220(3) . ?
N1 C1 1.346(3) . ?
N1 N2 1.353(3) . ?
N1 C9 1.418(3) . ?
N2 N3 1.303(3) . ?
N3 C2 1.368(4) . ?
N4 C12 1.467(4) . ?
C1 C2 1.357(4) . ?
C2 C3 1.470(4) . ?
C3 C8 1.386(4) . ?
C3 C4 1.391(4) . ?
C4 C5 1.382(5) . ?
C5 C6 1.372(5) . ?
C6 C7 1.382(4) . ?
C7 C8 1.381(4) . ?
C9 C10 1.384(4) . ?
C9 C14 1.388(4) . ?
C10 C11 1.381(4) . ?
C11 C12 1.372(4) . ?
C12 C13 1.378(4) . ?
C13 C14 1.366(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
C1 N1 N2 109.9(2) . . ?
C1 N1 C9 129.3(2) . . ?
N2 N1 C9 120.7(2) . . ?
N3 N2 N1 107.3(2) . . ?
N2 N3 C2 109.4(2) . . ?
O1 N4 O2 123.6(3) . . ?
O1 N4 C12 118.3(3) . . ?
O2 N4 C12 118.1(3) . . ?
N1 C1 C2 105.9(2) . . ?
C1 C2 N3 107.5(2) . . ?
C1 C2 C3 130.0(2) . . ?
N3 C2 C3 122.5(2) . . ?
C8 C3 C4 118.8(3) . . ?
C8 C3 C2 120.4(2) . . ?
C4 C3 C2 120.8(3) . . ?
C5 C4 C3 120.2(3) . . ?
C6 C5 C4 121.3(3) . . ?
C5 C6 C7 118.3(3) . . ?
C8 C7 C6 121.5(3) . . ?
C8 C7 Br1 118.7(2) . . ?
C6 C7 Br1 119.8(2) . . ?
C7 C8 C3 119.9(3) . . ?
C10 C9 C14 120.5(2) . . ?
C10 C9 N1 119.8(2) . . ?
C14 C9 N1 119.8(2) . . ?
C11 C10 C9 119.7(3) . . ?
C12 C11 C10 118.7(3) . . ?
C11 C12 C13 122.3(3) . . ?
C11 C12 N4 118.7(3) . . ?
C13 C12 N4 119.0(3) . . ?
C14 C13 C12 118.9(3) . . ?
C13 C14 C9 119.9(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
C1 N1 N2 N3 -0.2(3) . . . . ?
C9 N1 N2 N3 -178.9(2) . . . . ?
N1 N2 N3 C2 0.1(3) . . . . ?
N2 N1 C1 C2 0.2(3) . . . . ?
C9 N1 C1 C2 178.8(3) . . . . ?
N1 C1 C2 N3 -0.2(3) . . . . ?
N1 C1 C2 C3 179.8(3) . . . . ?
N2 N3 C2 C1 0.1(3) . . . . ?
N2 N3 C2 C3 -179.9(3) . . . . ?
C1 C2 C3 C8 6.5(5) . . . . ?
N3 C2 C3 C8 -173.5(3) . . . . ?
C1 C2 C3 C4 -173.3(3) . . . . ?
N3 C2 C3 C4 6.7(4) . . . . ?
C8 C3 C4 C5 -0.4(4) . . . . ?
C2 C3 C4 C5 179.4(3) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
C5 C6 C7 Br1 -178.7(2) . . . . ?
C6 C7 C8 C3 -0.9(5) . . . . ?
Br1 C7 C8 C3 178.2(2) . . . . ?
C4 C3 C8 C7 0.9(4) . . . . ?
C2 C3 C8 C7 -178.9(3) . . . . ?
C1 N1 C9 C10 -4.5(4) . . . . ?
N2 N1 C9 C10 173.9(3) . . . . ?
C1 N1 C9 C14 175.6(3) . . . . ?
N2 N1 C9 C14 -5.9(4) . . . . ?
C14 C9 C10 C11 -0.2(4) . . . . ?
N1 C9 C10 C11 179.9(3) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C10 C11 C12 N4 -179.9(3) . . . . ?
O1 N4 C12 C11 177.9(3) . . . . ?
O2 N4 C12 C11 -2.0(4) . . . . ?
O1 N4 C12 C13 -1.2(4) . . . . ?
O2 N4 C12 C13 178.9(3) . . . . ?
C11 C12 C13 C14 0.5(5) . . . . ?
N4 C12 C13 C14 179.5(3) . . . . ?
C12 C13 C14 C9 0.0(5) . . . . ?
C10 C9 C14 C13 -0.1(5) . . . . ?
N1 C9 C14 C13 179.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5 N2 0.93 2.52 3.387(4) 154.6 2_645
C1 H1 O2 0.93 2.33 3.247(3) 169.3 2_746
C8 H8 O2 0.93 2.66 3.556(4) 161.2 2_746
C10 H10 O1 0.93 2.56 3.387(4) 148.0 2_746

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.057

#===END

data_19
_database_code_depnum_ccdc_archive 'CCDC 679567'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9 Br N4 O2'
_chemical_formula_sum            'C14 H9 Br N4 O2'
_chemical_formula_weight         345.16

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6141(15)
_cell_length_b                   12.0915(19)
_cell_length_c                   12.900(2)
_cell_angle_alpha                87.535(2)
_cell_angle_beta                 71.407(2)
_cell_angle_gamma                76.183(2)
_cell_volume                     1379.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3651
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      23.53

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1930
_exptl_absorpt_correction_T_max  0.7155
_exptl_absorpt_process_details   'bruker sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13109
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4834
_reflns_number_gt                3401
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'

_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)+(0.0748P)²+0.1560P] 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_extinction_coef       ?
_refine_ls_number_reflns         4834
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 -0.29941(5) 0.01074(4) 0.49306(4) 0.0885(2) Uani 1 1 d . . .
O1 O 0.9720(4) 0.2627(3) -0.3609(3) 0.1067(11) Uani 1 1 d . . .
O2 O 1.0098(4) 0.2847(3) -0.2122(3) 0.1015(10) Uani 1 1 d . . .
N1 N 0.3989(3) 0.1325(2) -0.0348(2) 0.0492(7) Uani 1 1 d . . .
N2 N 0.3133(4) 0.1042(3) -0.0900(3) 0.0741(9) Uani 1 1 d . . .
N3 N 0.1946(4) 0.0827(3) -0.0175(3) 0.0742(9) Uani 1 1 d . . .
N4 N 0.9383(4) 0.2610(3) -0.2660(4) 0.0756(9) Uani 1 1 d . . .
C1 C 0.3311(4) 0.1288(3) 0.0732(3) 0.0508(8) Uani 1 1 d . . .
H1 H 0.3661 0.1448 0.1289 0.061 Uiso 1 1 calc R . .
C2 C 0.2003(4) 0.0968(3) 0.0848(3) 0.0484(8) Uani 1 1 d . . .
C3 C 0.0807(4) 0.0786(3) 0.1831(3) 0.0496(8) Uani 1 1 d . . .
C4 C -0.0345(4) 0.0315(3) 0.1737(3) 0.0631(10) Uani 1 1 d . . .
H4 H -0.0357 0.0133 0.1047 0.076 Uiso 1 1 calc R . .
C5 C -0.1463(4) 0.0116(3) 0.2658(3) 0.0681(10) Uani 1 1 d . . .
H5 H -0.2221 -0.0201 0.2588 0.082 Uiso 1 1 calc R . .
C6 C -0.1455(4) 0.0388(3) 0.3675(3) 0.0598(9) Uani 1 1 d . . .
C7 C -0.0329(4) 0.0867(3) 0.3791(3) 0.0613(9) Uani 1 1 d . . .
H7 H -0.0328 0.1059 0.4481 0.074 Uiso 1 1 calc R . .
C8 C 0.0779(4) 0.1051(3) 0.2869(3) 0.0574(9) Uani 1 1 d . . .
H8 H 0.1536 0.1366 0.2946 0.069 Uiso 1 1 calc R . .
C9 C 0.5361(4) 0.1631(3) -0.0929(3) 0.0482(8) Uani 1 1 d . . .
C10 C 0.6137(4) 0.2037(3) -0.0358(3) 0.0597(9) Uani 1 1 d . . .
H10 H 0.5774 0.2099 0.0402 0.072 Uiso 1 1 calc R . .
C11 C 0.7466(4) 0.2354(3) -0.0926(3) 0.0656(10) Uani 1 1 d . . .
H11 H 0.8004 0.2624 -0.0551 0.079 Uiso 1 1 calc R . .
C12 C 0.7970(4) 0.2264(3) -0.2037(3) 0.0605(9) Uani 1 1 d . . .
C13 C 0.7203(4) 0.1851(3) -0.2625(3) 0.0594(9) Uani 1 1 d . . .
H13 H 0.7566 0.1795 -0.3385 0.071 Uiso 1 1 calc R . .
C14 C 0.5894(4) 0.1526(3) -0.2057(3) 0.0572(9) Uani 1 1 d . . .
H14 H 0.5371 0.1236 -0.2433 0.069 Uiso 1 1 calc R . .
Br1' Br -0.00865(5) 0.41132(4) 1.38440(3) 0.08024(19) Uani 1 1 d . . .
O1' O 0.6719(4) 0.2692(3) 0.2096(3) 0.0960(10) Uani 1 1 d . . .
O2' O 0.4691(5) 0.2081(4) 0.2520(3) 0.1208(13) Uani 1 1 d . . .
N1' N 0.4036(3) 0.3961(2) 0.7148(2) 0.0498(7) Uani 1 1 d . . .
N2' N 0.4932(4) 0.4508(3) 0.7460(3) 0.0654(8) Uani 1 1 d . . .
N3' N 0.4374(4) 0.4659(3) 0.8520(3) 0.0649(8) Uani 1 1 d . . .
N4' N 0.5546(5) 0.2550(3) 0.2756(3) 0.0793(10) Uani 1 1 d . . .
C1' C 0.2920(4) 0.3770(3) 0.8026(3) 0.0520(8) Uani 1 1 d . . .
H1' H 0.2163 0.3411 0.8031 0.062 Uiso 1 1 calc R . .
C2' C 0.3126(4) 0.4211(3) 0.8908(3) 0.0501(8) Uani 1 1 d . . .
C3' C 0.2313(4) 0.4204(3) 1.0084(3) 0.0497(8) Uani 1 1 d . . .
C4' C 0.2924(4) 0.4509(3) 1.0841(3) 0.0590(9) Uani 1 1 d . . .
H4' H 0.3831 0.4734 1.0595 0.071 Uiso 1 1 calc R . .
C5' C 0.2213(4) 0.4484(3) 1.1943(3) 0.0638(10) Uani 1 1 d . . .
H5' H 0.2633 0.4695 1.2440 0.077 Uiso 1 1 calc R . .
C6' C 0.0873(4) 0.4146(3) 1.2312(3) 0.0564(9) Uani 1 1 d . . .
C7' C 0.0237(4) 0.3837(3) 1.1571(3) 0.0559(9) Uani 1 1 d . . .
H7' H -0.0672 0.3615 1.1821 0.067 Uiso 1 1 calc R . .
C8' C 0.0962(4) 0.3863(3) 1.0472(3) 0.0542(8) Uani 1 1 d . . .
H8' H 0.0544 0.3648 0.9977 0.065 Uiso 1 1 calc R . .
C9' C 0.4415(4) 0.3622(3) 0.6034(3) 0.0513(8) Uani 1 1 d . . .
C10' C 0.3370(4) 0.3260(3) 0.5685(3) 0.0649(10) Uani 1 1 d . . .
H10' H 0.2422 0.3253 0.6173 0.078 Uiso 1 1 calc R . .
C11' C 0.3750(5) 0.2908(4) 0.4604(3) 0.0692(10) Uani 1 1 d . . .
H11' H 0.3060 0.2663 0.4359 0.083 Uiso 1 1 calc R . .
C12' C 0.5151(4) 0.2925(3) 0.3899(3) 0.0626(9) Uani 1 1 d . . .
C13' C 0.6193(4) 0.3297(3) 0.4226(3) 0.0619(9) Uani 1 1 d . . .
H13' H 0.7129 0.3322 0.3729 0.074 Uiso 1 1 calc R . .
C14' C 0.5825(4) 0.3634(3) 0.5310(3) 0.0609(9) Uani 1 1 d . . .
H14' H 0.6525 0.3868 0.5553 0.073 Uiso 1 1 calc R . .


_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 C6 1.895(4) . ?
O1 N4 1.163(5) . ?
O2 N4 1.206(5) . ?
N1 C1 1.340(4) . ?
N1 N2 1.353(4) . ?
N1 C9 1.421(4) . ?
N2 N3 1.299(4) . ?
N3 C2 1.357(4) . ?
N4 C12 1.488(5) . ?
C1 C2 1.365(4) . ?
C2 C3 1.465(5) . ?
C3 C8 1.380(5) . ?
C3 C4 1.400(5) . ?
C4 C5 1.383(5) . ?
C5 C6 1.369(6) . ?
C6 C7 1.394(5) . ?
C7 C8 1.371(5) . ?
C9 C10 1.376(5) . ?
C9 C14 1.380(5) . ?
C10 C11 1.389(5) . ?
C11 C12 1.359(5) . ?
C12 C13 1.389(5) . ?
C13 C14 1.377(5) . ?
Br1' C6' 1.898(4) . ?
O1' N4' 1.222(5) . ?
O2' N4' 1.219(5) . ?
N1' C1' 1.345(4) . ?
N1' N2' 1.363(4) . ?
N1' C9' 1.419(4) . ?
N2' N3' 1.303(4) . ?
N3' C2' 1.375(4) . ?
N4' C12' 1.464(5) . ?
C1' C2' 1.365(5) . ?
C2' C3' 1.469(5) . ?
C3' C8' 1.390(5) . ?
C3' C4' 1.392(5) . ?
C4' C5' 1.369(5) . ?
C5' C6' 1.378(5) . ?
C6' C7' 1.393(5) . ?
C7' C8' 1.368(5) . ?
C9' C14' 1.382(5) . ?
C9' C10' 1.385(5) . ?
C10' C11' 1.382(5) . ?
C11' C12' 1.369(5) . ?
C12' C13' 1.373(5) . ?
C13' C14' 1.382(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
C1 N1 N2 109.8(3) . . ?
C1 N1 C9 130.1(3) . . ?
N2 N1 C9 120.0(3) . . ?
N3 N2 N1 107.0(3) . . ?
N2 N3 C2 110.1(3) . . ?
O1 N4 O2 125.2(4) . . ?
O1 N4 C12 118.9(4) . . ?
O2 N4 C12 116.0(4) . . ?
N1 C1 C2 106.1(3) . . ?
N3 C2 C1 107.0(3) . . ?
N3 C2 C3 122.2(3) . . ?
C1 C2 C3 130.8(3) . . ?
C8 C3 C4 117.9(3) . . ?
C8 C3 C2 122.1(3) . . ?
C4 C3 C2 120.0(3) . . ?
C5 C4 C3 120.6(4) . . ?
C6 C5 C4 119.9(4) . . ?
C5 C6 C7 120.5(3) . . ?
C5 C6 Br1 119.4(3) . . ?
C7 C6 Br1 120.1(3) . . ?
C8 C7 C6 118.8(3) . . ?
C7 C8 C3 122.2(3) . . ?
C10 C9 C14 120.9(3) . . ?
C10 C9 N1 119.4(3) . . ?
C14 C9 N1 119.7(3) . . ?
C9 C10 C11 119.5(4) . . ?
C12 C11 C10 119.2(3) . . ?
C11 C12 C13 121.9(3) . . ?
C11 C12 N4 120.0(4) . . ?
C13 C12 N4 118.1(4) . . ?
C14 C13 C12 118.6(3) . . ?
C13 C14 C9 119.8(3) . . ?
C1' N1' N2' 110.3(3) . . ?
C1' N1' C9' 129.8(3) . . ?
N2' N1' C9' 119.8(3) . . ?
N3' N2' N1' 106.8(3) . . ?
N2' N3' C2' 109.9(3) . . ?
O2' N4' O1' 123.4(4) . . ?
O2' N4' C12' 117.5(4) . . ?
O1' N4' C12' 119.2(4) . . ?
N1' C1' C2' 105.9(3) . . ?
C1' C2' N3' 107.2(3) . . ?
C1' C2' C3' 130.9(3) . . ?
N3' C2' C3' 121.8(3) . . ?
C8' C3' C4' 118.3(3) . . ?
C8' C3' C2' 121.9(3) . . ?
C4' C3' C2' 119.7(3) . . ?
C5' C4' C3' 121.2(3) . . ?
C4' C5' C6' 119.6(3) . . ?
C5' C6' C7' 120.3(3) . . ?
C5' C6' Br1' 118.8(3) . . ?
C7' C6' Br1' 120.9(3) . . ?
C8' C7' C6' 119.4(3) . . ?
C7' C8' C3' 121.2(3) . . ?
C14' C9' C10' 120.5(3) . . ?
C14' C9' N1' 120.1(3) . . ?
C10' C9' N1' 119.4(3) . . ?
C11' C10' C9' 119.4(4) . . ?
C12' C11' C10' 119.4(4) . . ?
C11' C12' C13' 122.1(4) . . ?
C11' C12' N4' 119.1(4) . . ?
C13' C12' N4' 118.9(4) . . ?
C12' C13' C14' 118.7(3) . . ?
C9' C14' C13' 120.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 N3 -0.4(4) . . . . ?
C9 N1 N2 N3 -178.7(3) . . . . ?
N1 N2 N3 C2 0.3(4) . . . . ?
N2 N1 C1 C2 0.3(4) . . . . ?
C9 N1 C1 C2 178.4(3) . . . . ?
N2 N3 C2 C1 -0.1(4) . . . . ?
N2 N3 C2 C3 179.8(3) . . . . ?
N1 C1 C2 N3 -0.1(4) . . . . ?
N1 C1 C2 C3 180.0(3) . . . . ?
N3 C2 C3 C8 -172.6(3) . . . . ?
C1 C2 C3 C8 7.3(6) . . . . ?
N3 C2 C3 C4 8.3(5) . . . . ?
C1 C2 C3 C4 -171.9(4) . . . . ?
C8 C3 C4 C5 -0.5(5) . . . . ?
C2 C3 C4 C5 178.7(3) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C4 C5 C6 C7 0.2(6) . . . . ?
C4 C5 C6 Br1 -179.8(3) . . . . ?
C5 C6 C7 C8 -0.6(6) . . . . ?
Br1 C6 C7 C8 179.4(3) . . . . ?
C6 C7 C8 C3 0.5(5) . . . . ?
C4 C3 C8 C7 0.1(5) . . . . ?
C2 C3 C8 C7 -179.1(3) . . . . ?
C1 N1 C9 C10 -5.1(5) . . . . ?
N2 N1 C9 C10 172.9(3) . . . . ?
C1 N1 C9 C14 175.3(3) . . . . ?
N2 N1 C9 C14 -6.7(5) . . . . ?
C14 C9 C10 C11 0.6(5) . . . . ?
N1 C9 C10 C11 -179.0(3) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C10 C11 C12 C13 -0.7(6) . . . . ?
C10 C11 C12 N4 179.4(3) . . . . ?
O1 N4 C12 C11 -172.9(4) . . . . ?
O2 N4 C12 C11 7.6(5) . . . . ?
O1 N4 C12 C13 7.2(6) . . . . ?
O2 N4 C12 C13 -172.3(4) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
N4 C12 C13 C14 179.9(3) . . . . ?
C12 C13 C14 C9 1.0(5) . . . . ?
C10 C9 C14 C13 -1.3(5) . . . . ?
N1 C9 C14 C13 178.3(3) . . . . ?
C1' N1' N2' N3' -0.3(4) . . . . ?
C9' N1' N2' N3' -176.5(3) . . . . ?
N1' N2' N3' C2' 0.4(4) . . . . ?
N2' N1' C1' C2' 0.1(4) . . . . ?
C9' N1' C1' C2' 175.8(3) . . . . ?
N1' C1' C2' N3' 0.2(4) . . . . ?
N1' C1' C2' C3' -176.4(3) . . . . ?
N2' N3' C2' C1' -0.4(4) . . . . ?
N2' N3' C2' C3' 176.6(3) . . . . ?
C1' C2' C3' C8' -10.8(5) . . . . ?
N3' C2' C3' C8' 173.1(3) . . . . ?
C1' C2' C3' C4' 167.0(3) . . . . ?
N3' C2' C3' C4' -9.1(5) . . . . ?
C8' C3' C4' C5' -0.5(5) . . . . ?
C2' C3' C4' C5' -178.4(3) . . . . ?
C3' C4' C5' C6' 0.3(6) . . . . ?
C4' C5' C6' C7' -0.4(5) . . . . ?
C4' C5' C6' Br1' 179.8(3) . . . . ?
C5' C6' C7' C8' 0.6(5) . . . . ?
Br1' C6' C7' C8' -179.6(3) . . . . ?
C6' C7' C8' C3' -0.7(5) . . . . ?
C4' C3' C8' C7' 0.7(5) . . . . ?
C2' C3' C8' C7' 178.5(3) . . . . ?
C1' N1' C9' C14' -162.4(3) . . . . ?
N2' N1' C9' C14' 12.9(5) . . . . ?
C1' N1' C9' C10' 16.4(5) . . . . ?
N2' N1' C9' C10' -168.2(3) . . . . ?
C14' C9' C10' C11' 0.1(6) . . . . ?
N1' C9' C10' C11' -178.8(3) . . . . ?
C9' C10' C11' C12' -0.1(6) . . . . ?
C10' C11' C12' C13' -0.9(6) . . . . ?
C10' C11' C12' N4' 179.9(3) . . . . ?
O2' N4' C12' C11' -10.5(6) . . . . ?
O1' N4' C12' C11' 171.2(4) . . . . ?
O2' N4' C12' C13' 170.3(4) . . . . ?
O1' N4' C12' C13' -8.0(6) . . . . ?
C11' C12' C13' C14' 1.8(6) . . . . ?
N4' C12' C13' C14' -179.0(3) . . . . ?
C10' C9' C14' C13' 0.9(5) . . . . ?
N1' C9' C14' C13' 179.7(3) . . . . ?
C12' C13' C14' C9' -1.8(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O2' 0.93 2.36 3.279(5) 170.9 .
C10 H10 O2' 0.93 2.60 3.523(5) 174.4 .
C4 H4 N3 0.93 2.65 3.401(5) 138.8 2
C1' H1' O2 0.93 2.31 3.230(5) 168.4 1_456
C10' H10' O2 0.93 2.71 3.620(5) 164.7 1_456
C4' H4' N3' 0.93 2.60 3.334(5) 136.5 2_667

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.856
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.065

#===END


