# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

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

data_s2533
_database_code_depnum_ccdc_archive 'CCDC 1442372'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;


_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H15 N3 O3'
_chemical_formula_weight         225.25

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   16.652(2)
_cell_length_b                   6.8992(9)
_cell_length_c                   18.610(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2138.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2152
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      25.48

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9397
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10825
_diffrn_reflns_av_R_equivalents  0.1050
_diffrn_reflns_av_sigmaI/netI    0.0662
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         26.50
_reflns_number_total             2207
_reflns_number_gt                1558
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0408P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2207
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0911
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_restrained_S_all      0.926
_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 0.19407(6) 0.17737(16) 0.65172(5) 0.0183(3) Uani 1 1 d . . .
O2 O 0.45386(7) 0.14920(17) 0.58106(6) 0.0236(3) Uani 1 1 d . . .
N1 N 0.28497(8) 0.1191(2) 0.56185(7) 0.0189(3) Uani 1 1 d . . .
N2 N 0.40364(8) 0.1761(2) 0.63538(7) 0.0182(3) Uani 1 1 d . . .
N3 N 0.14473(8) 0.1032(2) 0.53986(7) 0.0200(3) Uani 1 1 d . . .
C1 C 0.20856(10) 0.1311(2) 0.58047(8) 0.0176(4) Uani 1 1 d . . .
C2 C 0.32361(10) 0.1634(2) 0.62490(8) 0.0172(4) Uani 1 1 d . . .
C3 C 0.43038(10) 0.2222(2) 0.70356(8) 0.0189(4) Uani 1 1 d . . .
C4 C 0.37571(9) 0.2499(2) 0.75891(9) 0.0191(4) Uani 1 1 d . . .
H4 H 0.3961 0.2787 0.8054 0.023 Uiso 1 1 calc R . .
C5 C 0.29225(10) 0.2379(2) 0.75032(8) 0.0176(4) Uani 1 1 d . . .
C6 C 0.27045(9) 0.1967(2) 0.68056(8) 0.0169(4) Uani 1 1 d . . .
C7 C 0.15483(10) 0.0389(3) 0.46558(8) 0.0244(4) Uani 1 1 d . . .
H7A H 0.1372 0.1417 0.4329 0.037 Uiso 1 1 calc R . .
H7B H 0.1225 -0.0778 0.4574 0.037 Uiso 1 1 calc R . .
H7C H 0.2115 0.0095 0.4567 0.037 Uiso 1 1 calc R . .
C8 C 0.06322(10) 0.1434(3) 0.56479(9) 0.0242(4) Uani 1 1 d . . .
H8A H 0.0377 0.0223 0.5802 0.036 Uiso 1 1 calc R . .
H8B H 0.0320 0.2010 0.5256 0.036 Uiso 1 1 calc R . .
H8C H 0.0653 0.2339 0.6053 0.036 Uiso 1 1 calc R . .
C9 C 0.51896(9) 0.2416(3) 0.71211(9) 0.0231(4) Uani 1 1 d . . .
H9A H 0.5315 0.2744 0.7621 0.035 Uiso 1 1 calc R . .
H9B H 0.5387 0.3445 0.6804 0.035 Uiso 1 1 calc R . .
H9C H 0.5449 0.1188 0.6995 0.035 Uiso 1 1 calc R . .
C10 C 0.23398(10) 0.2637(3) 0.81102(8) 0.0207(4) Uani 1 1 d . . .
H10A H 0.1962 0.3679 0.7992 0.031 Uiso 1 1 calc R . .
H10B H 0.2633 0.2973 0.8549 0.031 Uiso 1 1 calc R . .
H10C H 0.2043 0.1427 0.8186 0.031 Uiso 1 1 calc R . .
O1S O 0.39464(9) 0.0390(2) 0.42491(7) 0.0298(3) Uani 1 1 d . . .
H1S H 0.4447(15) -0.009(3) 0.4252(10) 0.048(7) Uiso 1 1 d . . .
H2S H 0.3839(14) 0.054(4) 0.4708(14) 0.069(8) 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 C1 1.3850(18) . ?
O1 C6 1.3869(19) . ?
O2 N2 1.3252(16) . ?
N1 C1 1.321(2) . ?
N1 C2 1.3727(19) . ?
N2 C2 1.350(2) . ?
N2 C3 1.382(2) . ?
N3 C1 1.318(2) . ?
N3 C8 1.461(2) . ?
N3 C7 1.462(2) . ?
C2 C6 1.382(2) . ?
C3 C4 1.388(2) . ?
C3 C9 1.490(2) . ?
C4 C5 1.401(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(2) . ?
C5 C10 1.500(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O1S H1S 0.90(2) . ?
O1S H2S 0.88(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 O1 C6 103.47(12) . . ?
C1 N1 C2 102.31(13) . . ?
O2 N2 C2 120.25(13) . . ?
O2 N2 C3 121.97(13) . . ?
C2 N2 C3 117.77(13) . . ?
C1 N3 C8 122.62(14) . . ?
C1 N3 C7 119.60(14) . . ?
C8 N3 C7 117.71(13) . . ?
N3 C1 N1 128.08(14) . . ?
N3 C1 O1 116.24(14) . . ?
N1 C1 O1 115.67(14) . . ?
N2 C2 N1 126.93(14) . . ?
N2 C2 C6 120.89(14) . . ?
N1 C2 C6 112.18(14) . . ?
N2 C3 C4 120.12(15) . . ?
N2 C3 C9 115.97(14) . . ?
C4 C3 C9 123.90(15) . . ?
C3 C4 C5 123.89(15) . . ?
C3 C4 H4 118.1 . . ?
C5 C4 H4 118.1 . . ?
C6 C5 C4 112.39(14) . . ?
C6 C5 C10 124.33(15) . . ?
C4 C5 C10 123.27(14) . . ?
C5 C6 C2 124.89(15) . . ?
C5 C6 O1 128.76(15) . . ?
C2 C6 O1 106.35(13) . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H1S O1S H2S 103.1(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
C8 N3 C1 N1 -172.50(16) . . . . ?
C7 N3 C1 N1 4.3(3) . . . . ?
C8 N3 C1 O1 8.0(2) . . . . ?
C7 N3 C1 O1 -175.17(14) . . . . ?
C2 N1 C1 N3 179.58(17) . . . . ?
C2 N1 C1 O1 -0.94(19) . . . . ?
C6 O1 C1 N3 179.67(15) . . . . ?
C6 O1 C1 N1 0.13(18) . . . . ?
O2 N2 C2 N1 1.7(3) . . . . ?
C3 N2 C2 N1 -179.78(16) . . . . ?
O2 N2 C2 C6 -178.10(14) . . . . ?
C3 N2 C2 C6 0.4(2) . . . . ?
C1 N1 C2 N2 -178.41(16) . . . . ?
C1 N1 C2 C6 1.41(18) . . . . ?
O2 N2 C3 C4 179.78(15) . . . . ?
C2 N2 C3 C4 1.3(2) . . . . ?
O2 N2 C3 C9 0.6(2) . . . . ?
C2 N2 C3 C9 -177.92(15) . . . . ?
N2 C3 C4 C5 -1.3(3) . . . . ?
C9 C3 C4 C5 177.81(16) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C3 C4 C5 C10 178.56(16) . . . . ?
C4 C5 C6 C2 2.2(2) . . . . ?
C10 C5 C6 C2 -176.71(16) . . . . ?
C4 C5 C6 O1 -178.75(15) . . . . ?
C10 C5 C6 O1 2.3(3) . . . . ?
N2 C2 C6 C5 -2.3(3) . . . . ?
N1 C2 C6 C5 177.83(16) . . . . ?
N2 C2 C6 O1 178.43(14) . . . . ?
N1 C2 C6 O1 -1.40(18) . . . . ?
C1 O1 C6 C5 -178.44(17) . . . . ?
C1 O1 C6 C2 0.75(16) . . . . ?

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
O1S H1S O2 0.90(2) 1.95(3) 2.8394(19) 171(2) 5_656
O1S H2S N1 0.88(3) 2.41(3) 3.184(2) 148(2) .
O1S H2S O2 0.88(3) 2.45(3) 3.1616(17) 138(2) .

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.044
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s2508m
_database_code_depnum_ccdc_archive 'CCDC 1442373'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 N3 O2'
_chemical_formula_weight         207.23

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)

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

_cell_length_a                   7.6207(7)
_cell_length_b                   12.3266(12)
_cell_length_c                   11.1367(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.726(2)
_cell_angle_gamma                90.00
_cell_volume                     1024.32(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3369
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.21

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9670
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8195
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         26.40
_reflns_number_total             2197
_reflns_number_gt                1928
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0537P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2.0(12)
_refine_ls_number_reflns         2197
_refine_ls_number_parameters     279
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9998(2) 0.17075(13) 0.69956(15) 0.0217(4) Uani 1 1 d . . .
O2 O 1.2640(2) -0.10546(14) 0.90500(18) 0.0294(4) Uani 1 1 d . . .
H2 H 1.2071 -0.1515 0.9377 0.044 Uiso 1 1 calc R . .
N1 N 0.9048(3) 0.31823(18) 0.5790(2) 0.0279(5) Uani 1 1 d . . .
N2 N 0.8840(3) 0.31348(18) 0.78876(19) 0.0241(5) Uani 1 1 d . . .
N3 N 0.9200(3) 0.23382(17) 0.99156(19) 0.0225(5) Uani 1 1 d . . .
C1 C 0.9264(3) 0.2732(2) 0.6891(2) 0.0217(5) Uani 1 1 d . . .
C2 C 0.9328(3) 0.23172(19) 0.8747(2) 0.0206(5) Uani 1 1 d . . .
C3 C 1.0033(3) 0.14493(19) 0.8205(2) 0.0198(5) Uani 1 1 d . . .
C4 C 1.0665(3) 0.05219(18) 0.8829(2) 0.0204(5) Uani 1 1 d . . .
C5 C 1.0525(3) 0.0539(2) 1.0064(2) 0.0227(6) Uani 1 1 d . . .
H5 H 1.0930 -0.0069 1.0568 0.027 Uiso 1 1 calc R . .
C6 C 0.9806(3) 0.14298(19) 1.0571(2) 0.0215(5) Uani 1 1 d . . .
C7 C 0.8234(5) 0.4245(2) 0.5578(3) 0.0420(8) Uani 1 1 d . . .
H7A H 0.7675 0.4439 0.6267 0.063 Uiso 1 1 calc R . .
H7B H 0.7321 0.4233 0.4819 0.063 Uiso 1 1 calc R . .
H7C H 0.9156 0.4781 0.5504 0.063 Uiso 1 1 calc R . .
C8 C 0.9650(4) 0.2658(2) 0.4776(2) 0.0304(6) Uani 1 1 d . . .
H8A H 1.0421 0.3156 0.4433 0.046 Uiso 1 1 calc R . .
H8B H 0.8608 0.2464 0.4140 0.046 Uiso 1 1 calc R . .
H8C H 1.0325 0.2001 0.5071 0.046 Uiso 1 1 calc R . .
C9 C 1.1425(3) -0.0415(2) 0.8223(2) 0.0243(6) Uani 1 1 d . . .
H9A H 1.0426 -0.0879 0.7805 0.029 Uiso 1 1 calc R . .
H9B H 1.2041 -0.0126 0.7589 0.029 Uiso 1 1 calc R . .
C10 C 0.9706(4) 0.1453(2) 1.1895(2) 0.0291(6) Uani 1 1 d . . .
H10A H 1.0034 0.0740 1.2261 0.044 Uiso 1 1 calc R . .
H10B H 0.8482 0.1634 1.1974 0.044 Uiso 1 1 calc R . .
H10C H 1.0537 0.2002 1.2321 0.044 Uiso 1 1 calc R . .
O3 O 0.4923(2) 0.15446(13) 0.80505(15) 0.0206(4) Uani 1 1 d . . .
O4 O 0.7379(2) -0.13452(14) 0.67571(16) 0.0253(4) Uani 1 1 d . . .
H4 H 0.6721 -0.1672 0.6172 0.038 Uiso 1 1 calc R . .
N4 N 0.3810(3) 0.29915(17) 0.8949(2) 0.0241(5) Uani 1 1 d . . .
N5 N 0.3998(3) 0.30247(18) 0.68420(19) 0.0223(5) Uani 1 1 d . . .
N6 N 0.4598(3) 0.22543(16) 0.49533(19) 0.0216(5) Uani 1 1 d . . .
C11 C 0.4217(3) 0.25840(19) 0.7937(2) 0.0208(5) Uani 1 1 d . . .
C12 C 0.4595(3) 0.22220(19) 0.6147(2) 0.0199(5) Uani 1 1 d . . .
C13 C 0.5169(3) 0.13256(18) 0.6887(2) 0.0186(5) Uani 1 1 d . . .
C14 C 0.5821(3) 0.0394(2) 0.6453(2) 0.0200(5) Uani 1 1 d . . .
C15 C 0.5860(3) 0.0442(2) 0.5202(2) 0.0228(5) Uani 1 1 d . . .
H15 H 0.6323 -0.0156 0.4827 0.027 Uiso 1 1 calc R . .
C16 C 0.5237(3) 0.1343(2) 0.4496(2) 0.0233(6) Uani 1 1 d . . .
C17 C 0.4126(3) 0.2396(2) 1.0105(2) 0.0260(6) Uani 1 1 d . . .
H17A H 0.4116 0.1615 0.9938 0.039 Uiso 1 1 calc R . .
H17B H 0.3182 0.2570 1.0554 0.039 Uiso 1 1 calc R . .
H17C H 0.5294 0.2602 1.0599 0.039 Uiso 1 1 calc R . .
C18 C 0.3242(4) 0.4121(2) 0.8964(3) 0.0278(6) Uani 1 1 d . . .
H18A H 0.4252 0.4567 0.9374 0.042 Uiso 1 1 calc R . .
H18B H 0.2259 0.4178 0.9407 0.042 Uiso 1 1 calc R . .
H18C H 0.2833 0.4377 0.8120 0.042 Uiso 1 1 calc R . .
C19 C 0.6350(3) -0.0590(2) 0.7261(2) 0.0225(5) Uani 1 1 d . . .
H19A H 0.7042 -0.0347 0.8066 0.027 Uiso 1 1 calc R . .
H19B H 0.5250 -0.0953 0.7402 0.027 Uiso 1 1 calc R . .
C20 C 0.5161(4) 0.1346(2) 0.3140(3) 0.0298(6) Uani 1 1 d . . .
H20A H 0.3908 0.1363 0.2703 0.045 Uiso 1 1 calc R . .
H20B H 0.5740 0.0689 0.2910 0.045 Uiso 1 1 calc R . .
H20C H 0.5787 0.1987 0.2919 0.045 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 C1 1.377(3) . ?
O1 C3 1.379(3) . ?
O2 C9 1.408(3) . ?
O2 H2 0.8400 . ?
N1 C1 1.325(3) . ?
N1 C7 1.448(3) . ?
N1 C8 1.454(3) . ?
N2 C1 1.315(3) . ?
N2 C2 1.388(3) . ?
N3 C2 1.325(3) . ?
N3 C6 1.365(3) . ?
C2 C3 1.389(3) . ?
C3 C4 1.373(3) . ?
C4 C5 1.401(4) . ?
C4 C9 1.511(4) . ?
C5 C6 1.396(4) . ?
C5 H5 0.9500 . ?
C6 C10 1.493(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O3 C13 1.374(3) . ?
O3 C11 1.385(3) . ?
O4 C19 1.405(3) . ?
O4 H4 0.8400 . ?
N4 C11 1.328(3) . ?
N4 C17 1.459(3) . ?
N4 C18 1.460(3) . ?
N5 C11 1.314(3) . ?
N5 C12 1.388(3) . ?
N6 C12 1.331(3) . ?
N6 C16 1.363(3) . ?
C12 C13 1.394(3) . ?
C13 C14 1.377(3) . ?
C14 C15 1.402(4) . ?
C14 C19 1.515(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 C20 1.500(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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 O1 C3 102.77(18) . . ?
C9 O2 H2 109.5 . . ?
C1 N1 C7 119.9(2) . . ?
C1 N1 C8 122.2(2) . . ?
C7 N1 C8 117.9(2) . . ?
C1 N2 C2 103.3(2) . . ?
C2 N3 C6 115.1(2) . . ?
N2 C1 N1 128.1(2) . . ?
N2 C1 O1 116.1(2) . . ?
N1 C1 O1 115.8(2) . . ?
N3 C2 N2 126.9(2) . . ?
N3 C2 C3 123.6(2) . . ?
N2 C2 C3 109.5(2) . . ?
C4 C3 O1 128.4(2) . . ?
C4 C3 C2 123.3(2) . . ?
O1 C3 C2 108.3(2) . . ?
C3 C4 C5 113.2(2) . . ?
C3 C4 C9 122.5(2) . . ?
C5 C4 C9 124.3(2) . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
N3 C6 C5 123.1(2) . . ?
N3 C6 C10 115.6(2) . . ?
C5 C6 C10 121.2(2) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C4 113.4(2) . . ?
O2 C9 H9A 108.9 . . ?
C4 C9 H9A 108.9 . . ?
O2 C9 H9B 108.9 . . ?
C4 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 O3 C11 102.73(18) . . ?
C19 O4 H4 109.5 . . ?
C11 N4 C17 122.3(2) . . ?
C11 N4 C18 119.5(2) . . ?
C17 N4 C18 117.8(2) . . ?
C11 N5 C12 103.2(2) . . ?
C12 N6 C16 115.0(2) . . ?
N5 C11 N4 128.6(2) . . ?
N5 C11 O3 116.2(2) . . ?
N4 C11 O3 115.2(2) . . ?
N6 C12 N5 127.1(2) . . ?
N6 C12 C13 123.3(2) . . ?
N5 C12 C13 109.6(2) . . ?
O3 C13 C14 128.5(2) . . ?
O3 C13 C12 108.3(2) . . ?
C14 C13 C12 123.1(2) . . ?
C13 C14 C15 113.3(2) . . ?
C13 C14 C19 122.1(2) . . ?
C15 C14 C19 124.6(2) . . ?
C16 C15 C14 121.6(2) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
N6 C16 C15 123.7(2) . . ?
N6 C16 C20 115.5(2) . . ?
C15 C16 C20 120.7(2) . . ?
N4 C17 H17A 109.5 . . ?
N4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 C14 113.3(2) . . ?
O4 C19 H19A 108.9 . . ?
C14 C19 H19A 108.9 . . ?
O4 C19 H19B 108.9 . . ?
C14 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C1 N1 179.0(2) . . . . ?
C2 N2 C1 O1 0.1(3) . . . . ?
C7 N1 C1 N2 -0.8(4) . . . . ?
C8 N1 C1 N2 177.5(2) . . . . ?
C7 N1 C1 O1 178.0(2) . . . . ?
C8 N1 C1 O1 -3.7(3) . . . . ?
C3 O1 C1 N2 -0.1(3) . . . . ?
C3 O1 C1 N1 -179.1(2) . . . . ?
C6 N3 C2 N2 -179.0(2) . . . . ?
C6 N3 C2 C3 -0.4(3) . . . . ?
C1 N2 C2 N3 178.6(2) . . . . ?
C1 N2 C2 C3 -0.1(3) . . . . ?
C1 O1 C3 C4 -178.7(2) . . . . ?
C1 O1 C3 C2 0.1(2) . . . . ?
N3 C2 C3 C4 0.2(4) . . . . ?
N2 C2 C3 C4 178.9(2) . . . . ?
N3 C2 C3 O1 -178.7(2) . . . . ?
N2 C2 C3 O1 0.0(3) . . . . ?
O1 C3 C4 C5 178.8(2) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
O1 C3 C4 C9 -1.4(4) . . . . ?
C2 C3 C4 C9 179.9(2) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C9 C4 C5 C6 -179.9(2) . . . . ?
C2 N3 C6 C5 0.5(3) . . . . ?
C2 N3 C6 C10 178.7(2) . . . . ?
C4 C5 C6 N3 -0.3(4) . . . . ?
C4 C5 C6 C10 -178.4(2) . . . . ?
C3 C4 C9 O2 154.9(2) . . . . ?
C5 C4 C9 O2 -25.3(3) . . . . ?
C12 N5 C11 N4 -177.9(2) . . . . ?
C12 N5 C11 O3 0.2(3) . . . . ?
C17 N4 C11 N5 179.6(2) . . . . ?
C18 N4 C11 N5 -8.4(4) . . . . ?
C17 N4 C11 O3 1.5(3) . . . . ?
C18 N4 C11 O3 173.4(2) . . . . ?
C13 O3 C11 N5 0.2(2) . . . . ?
C13 O3 C11 N4 178.59(19) . . . . ?
C16 N6 C12 N5 -179.0(2) . . . . ?
C16 N6 C12 C13 -0.9(3) . . . . ?
C11 N5 C12 N6 177.7(2) . . . . ?
C11 N5 C12 C13 -0.6(3) . . . . ?
C11 O3 C13 C14 -179.1(2) . . . . ?
C11 O3 C13 C12 -0.6(2) . . . . ?
N6 C12 C13 O3 -177.63(19) . . . . ?
N5 C12 C13 O3 0.7(3) . . . . ?
N6 C12 C13 C14 1.0(4) . . . . ?
N5 C12 C13 C14 179.4(2) . . . . ?
O3 C13 C14 C15 178.8(2) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
O3 C13 C14 C19 1.5(4) . . . . ?
C12 C13 C14 C19 -176.9(2) . . . . ?
C13 C14 C15 C16 -1.9(3) . . . . ?
C19 C14 C15 C16 175.3(2) . . . . ?
C12 N6 C16 C15 -0.6(3) . . . . ?
C12 N6 C16 C20 177.0(2) . . . . ?
C14 C15 C16 N6 2.1(4) . . . . ?
C14 C15 C16 C20 -175.4(2) . . . . ?
C13 C14 C19 O4 -165.2(2) . . . . ?
C15 C14 C19 O4 17.8(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
O4 H4 N6 0.84 1.95 2.777(3) 166.0 2_646
O2 H2 N3 0.84 1.97 2.806(3) 176.5 2_747

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.043
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s3495b-29
_database_code_depnum_ccdc_archive 'CCDC 1442374'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 Br N3 O4'
_chemical_formula_sum            'C15 H16 Br N3 O4'
_chemical_formula_weight         382.22

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pca21
_symmetry_space_group_name_Hall  P2c-2ac

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

_cell_length_a                   27.5444(14)
_cell_length_b                   4.0773(4)
_cell_length_c                   26.9996(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3032.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7560
_cell_measurement_theta_min      1.6283
_cell_measurement_theta_max      25.6266

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    2.736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66861
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.68890
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Station I19, Diamond'
_diffrn_radiation_monochromator  silicon
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18225
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         24.21
_reflns_number_total             5167
_reflns_number_gt                4672
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0764P)²+9.9278P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.012(14)
_refine_ls_number_reflns         5167
_refine_ls_number_parameters     423
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1520
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.65779(3) -1.0608(2) 0.83790(3) 0.0312(2) Uani 1 1 d . . .
O1 O 0.7594(2) -0.6958(16) 0.80925(19) 0.0292(14) Uani 1 1 d . . .
O2 O 0.7212(2) -0.3845(16) 0.6472(2) 0.0301(14) Uani 1 1 d . . .
O3 O 0.6936(2) -0.476(2) 0.5446(2) 0.0499(19) Uani 1 1 d . . .
O4 O 0.5823(2) -0.7963(17) 0.6609(2) 0.0377(15) Uani 1 1 d . . .
H4 H 0.5707 -0.7137 0.6859 0.057 Uiso 1 1 calc RD . .
N1 N 0.7856(3) -0.4391(19) 0.7391(2) 0.0291(16) Uani 1 1 d . . .
N2 N 0.6953(3) -0.363(3) 0.4941(3) 0.052(3) Uani 1 1 d . . .
N3 N 0.8355(3) -0.455(2) 0.8107(3) 0.0326(18) Uani 1 1 d . . .
C1 C 0.6776(3) -0.857(2) 0.7783(3) 0.0279(19) Uani 1 1 d . . .
C2 C 0.7218(3) -0.714(2) 0.7743(3) 0.0284(19) Uani 1 1 d . . .
C3 C 0.7953(3) -0.518(2) 0.7852(3) 0.0271(19) Uani 1 1 d . . .
C4 C 0.7386(3) -0.551(2) 0.7314(3) 0.0269(18) Uani 1 1 d . . .
C5 C 0.7076(3) -0.542(2) 0.6907(3) 0.0285(19) Uani 1 1 d . . .
C6 C 0.7463(4) -0.610(2) 0.6135(3) 0.032(2) Uani 1 1 d . . .
H6A H 0.7329 -0.8289 0.6167 0.038 Uiso 1 1 calc R . .
H6B H 0.7806 -0.6188 0.6216 0.038 Uiso 1 1 calc R . .
C7 C 0.7397(3) -0.488(2) 0.5610(3) 0.031(2) Uani 1 1 d . . .
C8 C 0.7408(3) -0.327(3) 0.4844(3) 0.035(2) Uani 1 1 d . . .
C9 C 0.7709(3) -0.402(2) 0.5258(3) 0.032(2) Uani 1 1 d . . .
H9 H 0.8046 -0.3940 0.5278 0.039 Uiso 1 1 calc R . .
C10 C 0.7576(4) -0.215(3) 0.4343(3) 0.045(3) Uani 1 1 d . . .
H10A H 0.7837 -0.0610 0.4381 0.068 Uiso 1 1 calc R . .
H10B H 0.7312 -0.1119 0.4171 0.068 Uiso 1 1 calc R . .
H10C H 0.7688 -0.4006 0.4156 0.068 Uiso 1 1 calc R . .
C11 C 0.6617(3) -0.678(2) 0.6941(3) 0.0265(18) Uani 1 1 d . . .
C12 C 0.6274(3) -0.647(3) 0.6502(3) 0.034(2) Uani 1 1 d . . .
H12A H 0.6223 -0.4173 0.6426 0.041 Uiso 1 1 calc R . .
H12B H 0.6418 -0.7514 0.6215 0.041 Uiso 1 1 calc R . .
C13 C 0.6465(3) -0.843(2) 0.7378(3) 0.0268(18) Uani 1 1 d . . .
H13 H 0.6161 -0.9413 0.7393 0.032 Uiso 1 1 calc R . .
C14 C 0.8751(3) -0.276(3) 0.7859(3) 0.036(2) Uani 1 1 d . . .
H14A H 0.8624 -0.0821 0.7706 0.054 Uiso 1 1 calc R . .
H14B H 0.8895 -0.4144 0.7611 0.054 Uiso 1 1 calc R . .
H14C H 0.8993 -0.2165 0.8099 0.054 Uiso 1 1 calc R . .
C15 C 0.8445(4) -0.596(3) 0.8599(3) 0.036(2) Uani 1 1 d . . .
H15A H 0.8733 -0.7278 0.8589 0.054 Uiso 1 1 calc R . .
H15B H 0.8173 -0.7300 0.8694 0.054 Uiso 1 1 calc R . .
H15C H 0.8486 -0.4226 0.8836 0.054 Uiso 1 1 calc R . .
Br2 Br 0.88489(3) 0.1768(2) 0.46677(3) 0.0332(2) Uani 1 1 d . . .
O5 O 0.9798(2) 0.5823(15) 0.50590(18) 0.0277(13) Uani 1 1 d . . .
O6 O 0.9583(2) 0.4444(16) 0.67586(19) 0.0300(14) Uani 1 1 d . . .
O7 O 0.9647(2) 0.1514(17) 0.7757(2) 0.0372(15) Uani 1 1 d . . .
O8 O 0.8328(2) -0.1145(18) 0.6513(2) 0.0377(16) Uani 1 1 d . . .
H8 H 0.8172 -0.1661 0.6759 0.057 Uiso 1 1 calc R . .
N4 N 1.0107(2) 0.6807(19) 0.5828(2) 0.0284(16) Uani 1 1 d . . .
N5 N 0.9750(3) 0.231(2) 0.8258(2) 0.0388(19) Uani 1 1 d . . .
N6 N 1.0494(3) 0.902(2) 0.5110(2) 0.0320(17) Uani 1 1 d . . .
C16 C 0.9072(3) 0.260(2) 0.5316(3) 0.0276(19) Uani 1 1 d . . .
C17 C 0.9494(3) 0.436(2) 0.5400(3) 0.0283(19) Uani 1 1 d . . .
C18 C 1.0157(3) 0.727(2) 0.5351(3) 0.0275(18) Uani 1 1 d . . .
C19 C 0.9686(3) 0.490(2) 0.5869(3) 0.0246(17) Uani 1 1 d . . .
C20 C 0.9434(3) 0.377(2) 0.6280(3) 0.0248(18) Uani 1 1 d . . .
C21 C 0.9962(3) 0.223(2) 0.6928(3) 0.0282(19) Uani 1 1 d . . .
H21A H 1.0266 0.2719 0.6762 0.034 Uiso 1 1 calc R . .
H21B H 0.9874 -0.0023 0.6857 0.034 Uiso 1 1 calc R . .
C22 C 1.0014(3) 0.272(2) 0.7472(3) 0.0257(18) Uani 1 1 d . . .
C23 C 1.0166(3) 0.384(3) 0.8250(3) 0.034(2) Uani 1 1 d . . .
C24 C 1.0348(3) 0.417(2) 0.7752(3) 0.031(2) Uani 1 1 d . . .
H24 H 1.0634 0.5170 0.7650 0.037 Uiso 1 1 calc R . .
C25 C 1.0396(3) 0.508(3) 0.8717(3) 0.035(2) Uani 1 1 d . . .
H25A H 1.0643 0.3566 0.8822 0.052 Uiso 1 1 calc R . .
H25B H 1.0154 0.5269 0.8970 0.052 Uiso 1 1 calc R . .
H25C H 1.0540 0.7186 0.8657 0.052 Uiso 1 1 calc R . .
C26 C 0.9002(3) 0.192(2) 0.6209(3) 0.0296(19) Uani 1 1 d . . .
C27 C 0.8738(3) 0.072(2) 0.6658(3) 0.0296(19) Uani 1 1 d . . .
H27A H 0.8953 -0.0632 0.6856 0.035 Uiso 1 1 calc R . .
H27B H 0.8635 0.2565 0.6858 0.035 Uiso 1 1 calc R . .
C28 C 0.8828(3) 0.136(2) 0.5729(3) 0.0276(19) Uani 1 1 d . . .
H28 H 0.8546 0.0145 0.5684 0.033 Uiso 1 1 calc R . .
C29 C 1.0891(3) 1.043(3) 0.5380(3) 0.035(2) Uani 1 1 d . . .
H29A H 1.1147 0.8846 0.5411 0.053 Uiso 1 1 calc R . .
H29B H 1.0782 1.1072 0.5703 0.053 Uiso 1 1 calc R . .
H29C H 1.1009 1.2322 0.5206 0.053 Uiso 1 1 calc R . .
C30 C 1.0536(4) 0.887(3) 0.4571(3) 0.041(2) Uani 1 1 d . . .
H30A H 1.0648 1.0948 0.4448 0.062 Uiso 1 1 calc R . .
H30B H 1.0224 0.8384 0.4429 0.062 Uiso 1 1 calc R . .
H30C H 1.0763 0.7188 0.4480 0.062 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 C1 1.893(8) . ?
O1 C3 1.389(10) . ?
O1 C2 1.401(9) . ?
O2 C5 1.391(10) . ?
O2 C6 1.466(11) . ?
O3 C7 1.345(12) . ?
O3 N2 1.441(10) . ?
O4 C12 1.412(11) . ?
O4 H4 0.8200 . ?
N1 C3 1.313(10) . ?
N1 C4 1.388(11) . ?
N2 C8 1.287(13) . ?
N3 C3 1.329(11) . ?
N3 C15 1.467(10) . ?
N3 C14 1.473(12) . ?
C1 C2 1.354(12) . ?
C1 C13 1.390(11) . ?
C2 C4 1.413(11) . ?
C4 C5 1.394(11) . ?
C5 C11 1.380(12) . ?
C6 C7 1.514(11) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C9 1.327(12) . ?
C8 C9 1.427(12) . ?
C8 C10 1.502(11) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C13 1.422(11) . ?
C11 C12 1.522(11) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
Br2 C16 1.887(8) . ?
O5 C17 1.382(10) . ?
O5 C18 1.397(10) . ?
O6 C20 1.385(9) . ?
O6 C21 1.454(10) . ?
O7 C22 1.362(10) . ?
O7 N5 1.419(9) . ?
O8 C27 1.415(11) . ?
O8 H8 0.8200 . ?
N4 C18 1.309(10) . ?
N4 C19 1.399(11) . ?
N5 C23 1.307(12) . ?
N6 C18 1.336(11) . ?
N6 C29 1.435(11) . ?
N6 C30 1.462(10) . ?
C16 C17 1.381(12) . ?
C16 C28 1.396(12) . ?
C17 C19 1.390(11) . ?
C19 C20 1.389(11) . ?
C20 C26 1.419(13) . ?
C21 C22 1.488(10) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C24 1.329(12) . ?
C23 C24 1.440(11) . ?
C23 C25 1.497(11) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C28 1.401(11) . ?
C26 C27 1.496(11) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 103.8(6) . . ?
C5 O2 C6 111.2(7) . . ?
C7 O3 N2 107.0(7) . . ?
C12 O4 H4 109.5 . . ?
C3 N1 C4 104.6(7) . . ?
C8 N2 O3 105.1(7) . . ?
C3 N3 C15 122.2(8) . . ?
C3 N3 C14 118.4(7) . . ?
C15 N3 C14 118.7(7) . . ?
C2 C1 C13 118.4(7) . . ?
C2 C1 Br1 121.1(6) . . ?
C13 C1 Br1 120.5(6) . . ?
C1 C2 O1 129.2(7) . . ?
C1 C2 C4 124.1(7) . . ?
O1 C2 C4 106.7(7) . . ?
N1 C3 N3 127.9(8) . . ?
N1 C3 O1 115.2(7) . . ?
N3 C3 O1 116.9(7) . . ?
N1 C4 C5 133.0(7) . . ?
N1 C4 C2 109.6(7) . . ?
C5 C4 C2 117.3(8) . . ?
C11 C5 O2 119.3(7) . . ?
C11 C5 C4 119.9(7) . . ?
O2 C5 C4 120.7(8) . . ?
O2 C6 C7 108.6(7) . . ?
O2 C6 H6A 110.0 . . ?
C7 C6 H6A 110.0 . . ?
O2 C6 H6B 110.0 . . ?
C7 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
C9 C7 O3 111.5(8) . . ?
C9 C7 C6 132.6(9) . . ?
O3 C7 C6 115.7(7) . . ?
N2 C8 C9 112.5(8) . . ?
N2 C8 C10 121.2(8) . . ?
C9 C8 C10 126.3(9) . . ?
C7 C9 C8 103.9(8) . . ?
C7 C9 H9 128.1 . . ?
C8 C9 H9 128.1 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 C13 121.0(7) . . ?
C5 C11 C12 119.0(7) . . ?
C13 C11 C12 120.1(8) . . ?
O4 C12 C11 110.7(7) . . ?
O4 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C1 C13 C11 119.3(8) . . ?
C1 C13 H13 120.4 . . ?
C11 C13 H13 120.4 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 O5 C18 103.7(6) . . ?
C20 O6 C21 112.5(6) . . ?
C22 O7 N5 107.9(6) . . ?
C27 O8 H8 109.5 . . ?
C18 N4 C19 104.3(7) . . ?
C23 N5 O7 105.6(6) . . ?
C18 N6 C29 119.7(7) . . ?
C18 N6 C30 121.2(7) . . ?
C29 N6 C30 117.5(7) . . ?
C17 C16 C28 117.4(7) . . ?
C17 C16 Br2 121.3(6) . . ?
C28 C16 Br2 121.2(6) . . ?
C16 C17 O5 128.6(7) . . ?
C16 C17 C19 123.6(8) . . ?
O5 C17 C19 107.8(7) . . ?
N4 C18 N6 129.1(8) . . ?
N4 C18 O5 114.7(7) . . ?
N6 C18 O5 116.2(7) . . ?
C17 C19 C20 118.9(8) . . ?
C17 C19 N4 109.4(7) . . ?
C20 C19 N4 131.5(7) . . ?
O6 C20 C19 122.1(8) . . ?
O6 C20 C26 118.7(7) . . ?
C19 C20 C26 119.2(7) . . ?
O6 C21 C22 107.3(7) . . ?
O6 C21 H21A 110.3 . . ?
C22 C21 H21A 110.3 . . ?
O6 C21 H21B 110.3 . . ?
C22 C21 H21B 110.3 . . ?
H21A C21 H21B 108.5 . . ?
C24 C22 O7 110.6(7) . . ?
C24 C22 C21 133.4(8) . . ?
O7 C22 C21 115.9(7) . . ?
N5 C23 C24 111.3(7) . . ?
N5 C23 C25 121.2(7) . . ?
C24 C23 C25 127.4(8) . . ?
C22 C24 C23 104.5(8) . . ?
C22 C24 H24 127.8 . . ?
C23 C24 H24 127.8 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C28 C26 C20 119.8(7) . . ?
C28 C26 C27 122.0(8) . . ?
C20 C26 C27 118.2(7) . . ?
O8 C27 C26 109.9(7) . . ?
O8 C27 H27A 109.7 . . ?
C26 C27 H27A 109.7 . . ?
O8 C27 H27B 109.7 . . ?
C26 C27 H27B 109.7 . . ?
H27A C27 H27B 108.2 . . ?
C16 C28 C26 121.0(8) . . ?
C16 C28 H28 119.5 . . ?
C26 C28 H28 119.5 . . ?
N6 C29 H29A 109.5 . . ?
N6 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N6 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N6 C30 H30A 109.5 . . ?
N6 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N6 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 O3 N2 C8 1.8(12) . . . . ?
C13 C1 C2 O1 -179.5(8) . . . . ?
Br1 C1 C2 O1 2.1(13) . . . . ?
C13 C1 C2 C4 -0.2(14) . . . . ?
Br1 C1 C2 C4 -178.5(7) . . . . ?
C3 O1 C2 C1 -179.3(9) . . . . ?
C3 O1 C2 C4 1.3(9) . . . . ?
C4 N1 C3 N3 -177.9(9) . . . . ?
C4 N1 C3 O1 3.9(10) . . . . ?
C15 N3 C3 N1 -171.4(9) . . . . ?
C14 N3 C3 N1 -0.2(15) . . . . ?
C15 N3 C3 O1 6.8(13) . . . . ?
C14 N3 C3 O1 178.0(8) . . . . ?
C2 O1 C3 N1 -3.4(10) . . . . ?
C2 O1 C3 N3 178.2(8) . . . . ?
C3 N1 C4 C5 179.9(10) . . . . ?
C3 N1 C4 C2 -2.9(10) . . . . ?
C1 C2 C4 N1 -178.6(8) . . . . ?
O1 C2 C4 N1 0.9(10) . . . . ?
C1 C2 C4 C5 -0.9(14) . . . . ?
O1 C2 C4 C5 178.6(8) . . . . ?
C6 O2 C5 C11 -93.2(10) . . . . ?
C6 O2 C5 C4 90.1(10) . . . . ?
N1 C4 C5 C11 179.8(10) . . . . ?
C2 C4 C5 C11 2.8(13) . . . . ?
N1 C4 C5 O2 -3.5(16) . . . . ?
C2 C4 C5 O2 179.5(8) . . . . ?
C5 O2 C6 C7 154.0(7) . . . . ?
N2 O3 C7 C9 -1.7(12) . . . . ?
N2 O3 C7 C6 -178.5(9) . . . . ?
O2 C6 C7 C9 122.0(12) . . . . ?
O2 C6 C7 O3 -62.0(11) . . . . ?
O3 N2 C8 C9 -1.2(12) . . . . ?
O3 N2 C8 C10 179.1(10) . . . . ?
O3 C7 C9 C8 1.0(12) . . . . ?
C6 C7 C9 C8 177.1(10) . . . . ?
N2 C8 C9 C7 0.2(13) . . . . ?
C10 C8 C9 C7 179.9(10) . . . . ?
O2 C5 C11 C13 179.5(8) . . . . ?
C4 C5 C11 C13 -3.8(14) . . . . ?
O2 C5 C11 C12 -0.4(13) . . . . ?
C4 C5 C11 C12 176.3(9) . . . . ?
C5 C11 C12 O4 -179.3(8) . . . . ?
C13 C11 C12 O4 0.7(12) . . . . ?
C2 C1 C13 C11 -0.7(13) . . . . ?
Br1 C1 C13 C11 177.7(6) . . . . ?
C5 C11 C13 C1 2.7(14) . . . . ?
C12 C11 C13 C1 -177.3(8) . . . . ?
C22 O7 N5 C23 -1.3(10) . . . . ?
C28 C16 C17 O5 -179.9(8) . . . . ?
Br2 C16 C17 O5 2.5(14) . . . . ?
C28 C16 C17 C19 0.8(14) . . . . ?
Br2 C16 C17 C19 -176.8(7) . . . . ?
C18 O5 C17 C16 179.1(9) . . . . ?
C18 O5 C17 C19 -1.5(9) . . . . ?
C19 N4 C18 N6 177.9(9) . . . . ?
C19 N4 C18 O5 0.2(10) . . . . ?
C29 N6 C18 N4 5.8(15) . . . . ?
C30 N6 C18 N4 170.9(9) . . . . ?
C29 N6 C18 O5 -176.5(8) . . . . ?
C30 N6 C18 O5 -11.5(12) . . . . ?
C17 O5 C18 N4 0.9(10) . . . . ?
C17 O5 C18 N6 -177.1(8) . . . . ?
C16 C17 C19 C20 -3.0(14) . . . . ?
O5 C17 C19 C20 177.6(7) . . . . ?
C16 C17 C19 N4 -178.8(8) . . . . ?
O5 C17 C19 N4 1.7(10) . . . . ?
C18 N4 C19 C17 -1.2(10) . . . . ?
C18 N4 C19 C20 -176.3(9) . . . . ?
C21 O6 C20 C19 -82.3(10) . . . . ?
C21 O6 C20 C26 99.4(9) . . . . ?
C17 C19 C20 O6 -174.8(8) . . . . ?
N4 C19 C20 O6 0.0(15) . . . . ?
C17 C19 C20 C26 3.5(12) . . . . ?
N4 C19 C20 C26 178.2(9) . . . . ?
C20 O6 C21 C22 -168.0(7) . . . . ?
N5 O7 C22 C24 1.2(10) . . . . ?
N5 O7 C22 C21 -177.9(7) . . . . ?
O6 C21 C22 C24 -106.5(11) . . . . ?
O6 C21 C22 O7 72.4(10) . . . . ?
O7 N5 C23 C24 0.9(11) . . . . ?
O7 N5 C23 C25 -179.9(8) . . . . ?
O7 C22 C24 C23 -0.6(11) . . . . ?
C21 C22 C24 C23 178.3(10) . . . . ?
N5 C23 C24 C22 -0.2(12) . . . . ?
C25 C23 C24 C22 -179.3(10) . . . . ?
O6 C20 C26 C28 176.4(8) . . . . ?
C19 C20 C26 C28 -1.9(13) . . . . ?
O6 C20 C26 C27 -1.9(12) . . . . ?
C19 C20 C26 C27 179.8(8) . . . . ?
C28 C26 C27 O8 3.6(12) . . . . ?
C20 C26 C27 O8 -178.1(8) . . . . ?
C17 C16 C28 C26 0.9(13) . . . . ?
Br2 C16 C28 C26 178.5(7) . . . . ?
C20 C26 C28 C16 -0.3(13) . . . . ?
C27 C26 C28 C16 177.9(8) . . . . ?

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
O8 H8 N1 0.82 2.21 3.010(9) 163.7 .

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        24.21
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         1.607
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.133
