# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_gsn-1
_database_code_depnum_ccdc_archive 'CCDC 1547136'
_audit_update_record             
;
2017-04-29 deposited with the CCDC.
2018-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 N4'
_chemical_formula_sum            'C14 H12 N4'
_chemical_formula_weight         236.28

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'

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

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                   12.7026(11)
_cell_length_b                   6.3568(5)
_cell_length_c                   16.2435(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.604(2)
_cell_angle_gamma                90.00
_cell_volume                     1250.20(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6103
_cell_measurement_theta_min      3.35
_cell_measurement_theta_max      27.47

_exptl_crystal_description       chunk
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9531
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_process_details   'Higashi, T. (1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11650
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2864
_reflns_number_gt                1534
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0391P)²+0.8228P] 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     SHELXL
_refine_ls_extinction_coef       0.033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2864
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1508
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.1680
_refine_ls_wR_factor_gt          0.1336
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
C1 C 0.1567(2) 0.4094(4) 0.44547(17) 0.0546(7) Uani 1 1 d . . .
C2 C 0.1084(2) 0.2964(4) 0.49295(17) 0.0585(7) Uani 1 1 d . . .
H2 H 0.0567 0.1983 0.4630 0.070 Uiso 1 1 calc R . .
C3 C 0.0884(3) 0.2305(5) 0.6976(2) 0.0771(9) Uani 1 1 d . . .
H3 H 0.0565 0.1710 0.7366 0.093 Uiso 1 1 calc R . .
C4 C 0.1711(3) 0.3771(5) 0.7200(2) 0.0799(9) Uani 1 1 d . . .
H4 H 0.2046 0.4328 0.7746 0.096 Uiso 1 1 calc R . .
C5 C 0.1937(2) 0.4236(5) 0.6458(2) 0.0760(9) Uani 1 1 d . . .
H5 H 0.2464 0.5188 0.6396 0.091 Uiso 1 1 calc R . .
C6 C 0.3968(2) 0.6856(6) 0.54755(19) 0.0799(9) Uani 1 1 d . . .
H6 H 0.4723 0.6968 0.5748 0.096 Uiso 1 1 calc R . .
C7 C 0.3259(3) 0.8550(5) 0.5322(2) 0.0777(9) Uani 1 1 d . . .
H7 H 0.3430 0.9954 0.5461 0.093 Uiso 1 1 calc R . .
C8 C 0.2254(2) 0.7697(4) 0.49223(19) 0.0682(8) Uani 1 1 d . . .
H8 H 0.1589 0.8424 0.4727 0.082 Uiso 1 1 calc R . .
C9 C 0.1294(2) 0.3906(4) 0.35051(17) 0.0565(7) Uani 1 1 d . . .
C10 C 0.1888(3) 0.5018(5) 0.3069(2) 0.0843(10) Uani 1 1 d . . .
H10 H 0.2472 0.5864 0.3376 0.101 Uiso 1 1 calc R . .
C11 C 0.1624(3) 0.4893(6) 0.2177(2) 0.0954(11) Uani 1 1 d . . .
H11 H 0.2037 0.5652 0.1894 0.114 Uiso 1 1 calc R . .
C12 C 0.0777(3) 0.3685(6) 0.1714(2) 0.0814(10) Uani 1 1 d . . .
H12 H 0.0605 0.3602 0.1116 0.098 Uiso 1 1 calc R . .
C13 C 0.0184(3) 0.2601(6) 0.2136(2) 0.0931(11) Uani 1 1 d . . .
H13 H -0.0402 0.1767 0.1823 0.112 Uiso 1 1 calc R . .
C14 C 0.0434(3) 0.2710(5) 0.3021(2) 0.0845(10) Uani 1 1 d . . .
H14 H 0.0009 0.1955 0.3295 0.101 Uiso 1 1 calc R . .
N1 N 0.12550(17) 0.3061(3) 0.58218(14) 0.0591(6) Uani 1 1 d . . .
N2 N 0.05882(19) 0.1826(4) 0.61440(16) 0.0734(7) Uani 1 1 d . . .
N3 N 0.23912(16) 0.5617(3) 0.48598(13) 0.0565(6) Uani 1 1 d . . .
N4 N 0.34631(18) 0.5046(4) 0.51940(16) 0.0729(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
C1 C2 1.331(4) . ?
C1 N3 1.432(3) . ?
C1 C9 1.480(4) . ?
C2 N1 1.401(3) . ?
C2 H2 0.9300 . ?
C3 N2 1.323(4) . ?
C3 C4 1.368(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.353(4) . ?
C4 H4 0.9300 . ?
C5 N1 1.355(3) . ?
C5 H5 0.9300 . ?
C6 N4 1.330(4) . ?
C6 C7 1.377(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.358(4) . ?
C7 H7 0.9300 . ?
C8 N3 1.341(3) . ?
C8 H8 0.9300 . ?
C9 C14 1.368(4) . ?
C9 C10 1.376(4) . ?
C10 C11 1.388(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.350(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.350(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
N1 N2 1.370(3) . ?
N3 N4 1.354(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N3 120.0(2) . . ?
C2 C1 C9 123.8(2) . . ?
N3 C1 C9 116.2(2) . . ?
C1 C2 N1 128.4(3) . . ?
C1 C2 H2 115.8 . . ?
N1 C2 H2 115.8 . . ?
N2 C3 C4 112.8(3) . . ?
N2 C3 H3 123.6 . . ?
C4 C3 H3 123.6 . . ?
C5 C4 C3 105.3(3) . . ?
C5 C4 H4 127.3 . . ?
C3 C4 H4 127.3 . . ?
C4 C5 N1 107.5(3) . . ?
C4 C5 H5 126.3 . . ?
N1 C5 H5 126.3 . . ?
N4 C6 C7 113.2(3) . . ?
N4 C6 H6 123.4 . . ?
C7 C6 H6 123.4 . . ?
C8 C7 C6 104.1(3) . . ?
C8 C7 H7 128.0 . . ?
C6 C7 H7 128.0 . . ?
N3 C8 C7 107.7(3) . . ?
N3 C8 H8 126.1 . . ?
C7 C8 H8 126.1 . . ?
C14 C9 C10 117.2(3) . . ?
C14 C9 C1 122.6(3) . . ?
C10 C9 C1 120.2(3) . . ?
C9 C10 C11 120.7(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 118.7(3) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12 C13 C14 121.1(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C9 C14 C13 121.3(3) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C5 N1 N2 110.6(2) . . ?
C5 N1 C2 132.6(3) . . ?
N2 N1 C2 116.8(2) . . ?
C3 N2 N1 103.9(2) . . ?
C8 N3 N4 111.9(2) . . ?
C8 N3 C1 127.4(2) . . ?
N4 N3 C1 120.6(2) . . ?
C6 N4 N3 103.1(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
N3 C1 C2 N1 1.2(4) . . . . ?
C9 C1 C2 N1 -177.9(2) . . . . ?
N2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 N1 -0.1(4) . . . . ?
N4 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 N3 0.4(3) . . . . ?
C2 C1 C9 C14 7.3(4) . . . . ?
N3 C1 C9 C14 -171.9(3) . . . . ?
C2 C1 C9 C10 -175.2(3) . . . . ?
N3 C1 C9 C10 5.7(4) . . . . ?
C14 C9 C10 C11 -0.8(5) . . . . ?
C1 C9 C10 C11 -178.5(3) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C11 C12 C13 0.3(6) . . . . ?
C11 C12 C13 C14 -0.2(6) . . . . ?
C10 C9 C14 C13 0.9(5) . . . . ?
C1 C9 C14 C13 178.6(3) . . . . ?
C12 C13 C14 C9 -0.5(6) . . . . ?
C4 C5 N1 N2 -0.2(3) . . . . ?
C4 C5 N1 C2 176.4(3) . . . . ?
C1 C2 N1 C5 -1.2(5) . . . . ?
C1 C2 N1 N2 175.2(3) . . . . ?
C4 C3 N2 N1 -0.4(3) . . . . ?
C5 N1 N2 C3 0.4(3) . . . . ?
C2 N1 N2 C3 -176.8(2) . . . . ?
C7 C8 N3 N4 -1.0(3) . . . . ?
C7 C8 N3 C1 -177.3(3) . . . . ?
C2 C1 N3 C8 -97.6(3) . . . . ?
C9 C1 N3 C8 81.5(3) . . . . ?
C2 C1 N3 N4 86.3(3) . . . . ?
C9 C1 N3 N4 -94.5(3) . . . . ?
C7 C6 N4 N3 -0.8(3) . . . . ?
C8 N3 N4 C6 1.1(3) . . . . ?
C1 N3 N4 C6 177.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_0108-2
_database_code_depnum_ccdc_archive 'CCDC 1562256'
_audit_update_record             
;
2017-07-14 deposited with the CCDC.
2018-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 Br N4 O2'
_chemical_formula_sum            'C16 H15 Br N4 O2'
_chemical_formula_weight         375.23

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'
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 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   9.0450(6)
_cell_length_b                   9.5660(5)
_cell_length_c                   18.9448(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.971(2)
_cell_angle_gamma                90.00
_cell_volume                     1638.95(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8708
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.4

_exptl_crystal_description       chunk
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.39
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    2.523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2582
_exptl_absorpt_correction_T_max  0.3795
_exptl_absorpt_process_details   'Higashi, T. (1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15653
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_sigmaI/netI    0.0595
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3741
_reflns_number_gt                2089
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0299P)²+3.4730P] 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     SHELXL
_refine_ls_extinction_coef       0.0232(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3741
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1168
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
C1 C 0.9419(5) 0.3878(4) 0.3239(2) 0.0534(11) Uani 1 1 d . . .
H1 H 1.0362 0.3615 0.3103 0.064 Uiso 1 1 calc R . .
C2 C 0.9073(5) 0.3730(4) 0.3989(2) 0.0505(10) Uani 1 1 d . . .
C3 C 0.8139(5) 0.4699(5) 0.4320(2) 0.0526(11) Uani 1 1 d . . .
H3 H 0.7715 0.5411 0.4051 0.063 Uiso 1 1 calc R . .
C4 C 0.7831(5) 0.4627(4) 0.5027(2) 0.0519(11) Uani 1 1 d . . .
C5 C 0.8469(5) 0.3567(5) 0.5444(2) 0.0537(11) Uani 1 1 d . . .
C6 C 0.9374(5) 0.2593(5) 0.5133(2) 0.0575(12) Uani 1 1 d . . .
H6 H 0.9789 0.1874 0.5400 0.069 Uiso 1 1 calc R . .
C7 C 0.9664(5) 0.2693(4) 0.4412(2) 0.0536(11) Uani 1 1 d . . .
C8 C 0.6217(6) 0.6576(5) 0.4973(3) 0.0703(14) Uani 1 1 d . . .
H8A H 0.6932 0.7180 0.4761 0.106 Uiso 1 1 calc R . .
H8B H 0.5589 0.7115 0.5273 0.106 Uiso 1 1 calc R . .
H8C H 0.5628 0.6137 0.4609 0.106 Uiso 1 1 calc R . .
C9 C 0.8903(7) 0.2694(6) 0.6615(2) 0.0781(16) Uani 1 1 d . . .
H9A H 0.8622 0.1747 0.6512 0.117 Uiso 1 1 calc R . .
H9B H 0.8648 0.2918 0.7091 0.117 Uiso 1 1 calc R . .
H9C H 0.9951 0.2797 0.6559 0.117 Uiso 1 1 calc R . .
C10 C 0.8526(5) 0.4346(4) 0.2745(2) 0.0496(10) Uani 1 1 d . . .
C11 C 1.0319(8) 0.4797(8) 0.1163(3) 0.103(2) Uani 1 1 d . . .
H11 H 1.1156 0.4827 0.0884 0.124 Uiso 1 1 calc R . .
C12 C 0.8923(7) 0.5005(7) 0.0903(3) 0.0854(18) Uani 1 1 d . . .
H12 H 0.8639 0.5202 0.0439 0.103 Uiso 1 1 calc R . .
C13 C 0.8043(6) 0.4862(6) 0.1467(3) 0.0713(14) Uani 1 1 d . . .
H13 H 0.7017 0.4934 0.1467 0.086 Uiso 1 1 calc R . .
C14 C 0.5102(7) 0.5836(7) 0.3007(3) 0.0772(16) Uani 1 1 d . . .
H14 H 0.4457 0.6588 0.3046 0.093 Uiso 1 1 calc R . .
C15 C 0.4705(6) 0.4460(7) 0.3120(3) 0.0751(16) Uani 1 1 d . . .
H15 H 0.3778 0.4127 0.3243 0.090 Uiso 1 1 calc R . .
C16 C 0.5952(5) 0.3692(5) 0.3014(2) 0.0622(12) Uani 1 1 d . . .
H16 H 0.6051 0.2727 0.3051 0.075 Uiso 1 1 calc R . .
N1 N 0.8937(4) 0.4593(4) 0.20346(19) 0.0566(10) Uani 1 1 d . . .
N2 N 1.0370(5) 0.4546(6) 0.1855(2) 0.0908(16) Uani 1 1 d . . .
N3 N 0.7011(4) 0.4616(4) 0.28448(18) 0.0515(9) Uani 1 1 d . . .
N4 N 0.6501(5) 0.5957(4) 0.2837(2) 0.0683(11) Uani 1 1 d . . .
O1 O 0.6954(4) 0.5540(3) 0.53784(16) 0.0640(9) Uani 1 1 d . . .
O2 O 0.8145(4) 0.3614(4) 0.61419(16) 0.0707(9) Uani 1 1 d . . .
Br1 Br 1.09121(7) 0.13120(6) 0.40174(3) 0.0794(3) 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
C1 C10 1.305(6) . ?
C1 C2 1.467(6) . ?
C1 H1 0.9300 . ?
C2 C7 1.377(6) . ?
C2 C3 1.409(6) . ?
C3 C4 1.375(6) . ?
C3 H3 0.9300 . ?
C4 O1 1.361(5) . ?
C4 C5 1.403(6) . ?
C5 O2 1.360(5) . ?
C5 C6 1.379(6) . ?
C6 C7 1.398(6) . ?
C6 H6 0.9300 . ?
C7 Br1 1.900(4) . ?
C8 O1 1.414(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O2 1.424(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N3 1.411(5) . ?
C10 N1 1.422(5) . ?
C11 N2 1.332(7) . ?
C11 C12 1.362(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.351(7) . ?
C12 H12 0.9300 . ?
C13 N1 1.359(6) . ?
C13 H13 0.9300 . ?
C14 N4 1.316(7) . ?
C14 C15 1.382(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.365(7) . ?
C15 H15 0.9300 . ?
C16 N3 1.347(6) . ?
C16 H16 0.9300 . ?
N1 N2 1.347(5) . ?
N3 N4 1.363(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
C10 C1 C2 126.0(4) . . ?
C10 C1 H1 117.0 . . ?
C2 C1 H1 117.0 . . ?
C7 C2 C3 116.4(4) . . ?
C7 C2 C1 123.1(4) . . ?
C3 C2 C1 120.5(4) . . ?
C4 C3 C2 122.2(4) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
O1 C4 C3 125.0(4) . . ?
O1 C4 C5 115.3(4) . . ?
C3 C4 C5 119.8(4) . . ?
O2 C5 C6 125.3(4) . . ?
O2 C5 C4 115.4(4) . . ?
C6 C5 C4 119.3(4) . . ?
C5 C6 C7 119.6(4) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C2 C7 C6 122.7(4) . . ?
C2 C7 Br1 120.0(3) . . ?
C6 C7 Br1 117.3(3) . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C10 N3 123.9(4) . . ?
C1 C10 N1 124.6(4) . . ?
N3 C10 N1 111.5(4) . . ?
N2 C11 C12 113.5(5) . . ?
N2 C11 H11 123.3 . . ?
C12 C11 H11 123.3 . . ?
C13 C12 C11 104.7(5) . . ?
C13 C12 H12 127.6 . . ?
C11 C12 H12 127.6 . . ?
C12 C13 N1 107.1(5) . . ?
C12 C13 H13 126.4 . . ?
N1 C13 H13 126.4 . . ?
N4 C14 C15 112.0(5) . . ?
N4 C14 H14 124.0 . . ?
C15 C14 H14 124.0 . . ?
C16 C15 C14 105.8(5) . . ?
C16 C15 H15 127.1 . . ?
C14 C15 H15 127.1 . . ?
N3 C16 C15 105.9(5) . . ?
N3 C16 H16 127.0 . . ?
C15 C16 H16 127.0 . . ?
N2 N1 C13 111.6(4) . . ?
N2 N1 C10 120.1(4) . . ?
C13 N1 C10 128.2(4) . . ?
C11 N2 N1 103.0(5) . . ?
C16 N3 N4 112.2(4) . . ?
C16 N3 C10 127.5(4) . . ?
N4 N3 C10 120.0(4) . . ?
C14 N4 N3 104.0(4) . . ?
C4 O1 C8 117.3(4) . . ?
C5 O2 C9 118.8(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C7 147.6(5) . . . . ?
C10 C1 C2 C3 -34.7(7) . . . . ?
C7 C2 C3 C4 0.3(6) . . . . ?
C1 C2 C3 C4 -177.5(4) . . . . ?
C2 C3 C4 O1 179.1(4) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
O1 C4 C5 O2 -1.2(6) . . . . ?
C3 C4 C5 O2 177.6(4) . . . . ?
O1 C4 C5 C6 180.0(4) . . . . ?
C3 C4 C5 C6 -1.3(7) . . . . ?
O2 C5 C6 C7 -177.5(4) . . . . ?
C4 C5 C6 C7 1.3(7) . . . . ?
C3 C2 C7 C6 -0.4(6) . . . . ?
C1 C2 C7 C6 177.4(4) . . . . ?
C3 C2 C7 Br1 178.9(3) . . . . ?
C1 C2 C7 Br1 -3.3(6) . . . . ?
C5 C6 C7 C2 -0.4(7) . . . . ?
C5 C6 C7 Br1 -179.7(3) . . . . ?
C2 C1 C10 N3 -8.5(7) . . . . ?
C2 C1 C10 N1 174.1(4) . . . . ?
N2 C11 C12 C13 -0.6(9) . . . . ?
C11 C12 C13 N1 0.6(7) . . . . ?
N4 C14 C15 C16 0.2(6) . . . . ?
C14 C15 C16 N3 -0.2(5) . . . . ?
C12 C13 N1 N2 -0.5(6) . . . . ?
C12 C13 N1 C10 -179.1(5) . . . . ?
C1 C10 N1 N2 -9.9(7) . . . . ?
N3 C10 N1 N2 172.4(4) . . . . ?
C1 C10 N1 C13 168.6(5) . . . . ?
N3 C10 N1 C13 -9.1(6) . . . . ?
C12 C11 N2 N1 0.3(8) . . . . ?
C13 N1 N2 C11 0.1(7) . . . . ?
C10 N1 N2 C11 178.9(5) . . . . ?
C15 C16 N3 N4 0.1(5) . . . . ?
C15 C16 N3 C10 174.2(4) . . . . ?
C1 C10 N3 C16 -62.8(6) . . . . ?
N1 C10 N3 C16 114.9(5) . . . . ?
C1 C10 N3 N4 110.9(5) . . . . ?
N1 C10 N3 N4 -71.5(5) . . . . ?
C15 C14 N4 N3 -0.2(6) . . . . ?
C16 N3 N4 C14 0.0(5) . . . . ?
C10 N3 N4 C14 -174.5(4) . . . . ?
C3 C4 O1 C8 5.0(7) . . . . ?
C5 C4 O1 C8 -176.3(4) . . . . ?
C6 C5 O2 C9 7.2(7) . . . . ?
C4 C5 O2 C9 -171.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.093
