# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2102023'
loop_
_audit_author_name
_audit_author_address
'Sherin Anto' ' Vellore Institute of Technology'
_audit_update_record             
;
2022-05-11 deposited with the CCDC.	2022-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 N4 O'
_chemical_formula_sum            'C17 H14 N4 O'
_chemical_formula_weight         290.32

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   10.9221(11)
_cell_length_b                   11.2501(11)
_cell_length_c                   12.3823(11)
_cell_angle_alpha                90
_cell_angle_beta                 112.920(3)
_cell_angle_gamma                90
_cell_volume                     1401.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)

_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      33.15
_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7064
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_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  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17593
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.039
_diffrn_reflns_theta_max         29.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2018
_reflns_number_gt                1712
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'

_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'




_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0666P)²+0.6403P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2018
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1272
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36443(15) 0.25576(14) 0.79126(11) 0.0509(4) Uani 1 1 d . . . . .
H1 H 0.345038 0.250681 0.711302 0.061 Uiso 1 1 calc R U . . .
C2 C 0.41739(16) 0.15538(13) 0.85898(12) 0.0509(3) Uani 1 1 d . . . . .
H2 H 0.431016 0.086380 0.823811 0.061 Uiso 1 1 calc R U . . .
C3 C 0.44979(14) 0.15823(11) 0.97872(11) 0.0415(3) Uani 1 1 d . . . . .
H3 H 0.487110 0.092688 1.025835 0.050 Uiso 1 1 calc R U . . .
C4 C 0.42429(10) 0.26297(10) 1.02565(9) 0.0325(2) Uani 1 1 d . . . . .
C5 C 0.36813(11) 0.35718(10) 0.94688(10) 0.0345(3) Uani 1 1 d . . . . .
C6 C 0.39440(12) 0.41989(10) 1.12494(10) 0.0367(3) Uani 1 1 d . . . . .
H6 H 0.392359 0.468680 1.184845 0.044 Uiso 1 1 calc R U . . .
C7 C 0.44333(11) 0.30530(10) 1.14037(9) 0.0332(2) Uani 1 1 d . . . . .
C8 C 0.500000 0.23803(14) 1.250000 0.0335(3) Uani 1 2 d S T P . .
C9 C 0.28565(16) 0.56233(13) 0.95850(14) 0.0535(4) Uani 1 1 d . . . . .
H9A H 0.286748 0.615358 1.019612 0.080 Uiso 1 1 calc R U . . .
H9B H 0.195353 0.547065 0.906573 0.080 Uiso 1 1 calc R U . . .
H9C H 0.332506 0.598008 0.915336 0.080 Uiso 1 1 calc R U . . .
N1 N 0.33928(12) 0.35875(10) 0.83200(9) 0.0441(3) Uani 1 1 d . . . . .
N2 N 0.34944(10) 0.45169(9) 1.00967(8) 0.0382(3) Uani 1 1 d . . . . .
O1 O 0.500000 0.12863(11) 1.250000 0.0468(3) Uani 1 2 d S T P . .


_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 N1 1.3343(18) . ?
C1 C2 1.391(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.3841(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.3892(16) . ?
C3 H3 0.9300 . ?
C4 C5 1.4088(15) . ?
C4 C7 1.4346(14) . ?
C5 N1 1.3319(15) . ?
C5 N2 1.3785(15) . ?
C6 N2 1.3639(14) . ?
C6 C7 1.3800(15) . ?
C6 H6 0.9300 . ?
C7 C8 1.4643(13) . ?
C8 O1 1.2307(19) . ?
C9 N2 1.4466(16) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
N1 C1 C2 125.13(12) . . ?
N1 C1 H1 117.4 . . ?
C2 C1 H1 117.4 . . ?
C3 C2 C1 119.99(12) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 117.28(12) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
C3 C4 C5 116.92(10) . . ?
C3 C4 C7 136.09(11) . . ?
C5 C4 C7 106.97(10) . . ?
N1 C5 N2 124.52(11) . . ?
N1 C5 C4 127.40(11) . . ?
N2 C5 C4 108.06(10) . . ?
N2 C6 C7 110.62(10) . . ?
N2 C6 H6 124.7 . . ?
C7 C6 H6 124.7 . . ?
C6 C7 C4 105.90(9) . . ?
C6 C7 C8 127.76(10) . . ?
C4 C7 C8 126.32(10) . . ?
O1 C8 C7 121.12(7) . . ?
O1 C8 C7 121.12(7) . 2_657 ?
C7 C8 C7 117.75(13) . 2_657 ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 N1 C1 113.23(11) . . ?
C6 N2 C5 108.41(9) . . ?
C6 N2 C9 126.86(11) . . ?
C5 N2 C9 124.64(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.8(2) . . . . ?
C1 C2 C3 C4 1.4(2) . . . . ?
C2 C3 C4 C5 -0.26(18) . . . . ?
C2 C3 C4 C7 -178.48(13) . . . . ?
C3 C4 C5 N1 -1.81(18) . . . . ?
C7 C4 C5 N1 176.90(11) . . . . ?
C3 C4 C5 N2 179.42(10) . . . . ?
C7 C4 C5 N2 -1.87(13) . . . . ?
N2 C6 C7 C4 -1.29(13) . . . . ?
N2 C6 C7 C8 -179.75(10) . . . . ?
C3 C4 C7 C6 -179.75(13) . . . . ?
C5 C4 C7 C6 1.91(12) . . . . ?
C3 C4 C7 C8 -1.3(2) . . . . ?
C5 C4 C7 C8 -179.59(9) . . . . ?
C6 C7 C8 O1 155.86(9) . . . . ?
C4 C7 C8 O1 -22.30(13) . . . . ?
C6 C7 C8 C7 -24.14(9) . . . 2_657 ?
C4 C7 C8 C7 157.70(13) . . . 2_657 ?
N2 C5 N1 C1 -179.04(12) . . . . ?
C4 C5 N1 C1 2.38(19) . . . . ?
C2 C1 N1 C5 -1.0(2) . . . . ?
C7 C6 N2 C5 0.14(14) . . . . ?
C7 C6 N2 C9 176.85(12) . . . . ?
N1 C5 N2 C6 -177.71(11) . . . . ?
C4 C5 N2 C6 1.10(13) . . . . ?
N1 C5 N2 C9 5.49(19) . . . . ?
C4 C5 N2 C9 -175.70(12) . . . . ?

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_EP3_66_010722_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2191474'
loop_
_audit_author_name
_audit_author_address
'Sherin Anto'
; Vellore Institute of Technology
India
;
_audit_update_record             
;
2022-07-20 deposited with the CCDC.	2022-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 Br2 N4'
_chemical_formula_sum            'C17 H14 Br2 N4'
_chemical_formula_weight         434.14

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8514(7)
_cell_length_b                   8.4149(7)
_cell_length_c                   13.4259(12)
_cell_angle_alpha                100.609(3)
_cell_angle_beta                 105.510(3)
_cell_angle_gamma                95.703(3)
_cell_volume                     829.71(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9566
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      26.50

_exptl_crystal_description       block
_exptl_crystal_colour            gold
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    4.889
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5449
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23280
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.493
_diffrn_reflns_theta_max         28.309
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4105
_reflns_number_gt                2985
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+0.7248P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4105
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.01206(5) -0.31031(5) -0.07076(3) 0.06672(15) Uani 1 1 d . . . . .
Br2 Br 0.63856(6) 0.16436(5) 0.67095(3) 0.06483(15) Uani 1 1 d . . . . .
N1 N 0.5531(4) -0.2677(3) 0.0725(2) 0.0496(7) Uani 1 1 d . . . . .
N2 N 0.7509(3) -0.0322(3) 0.1882(2) 0.0463(6) Uani 1 1 d . . . . .
N3 N 0.7823(4) 0.6501(3) 0.4266(2) 0.0505(7) Uani 1 1 d . . . . .
N4 N 0.8415(4) 0.5808(4) 0.5960(2) 0.0535(7) Uani 1 1 d . . . . .
C1 C 0.4626(4) -0.0023(3) 0.1292(2) 0.0341(6) Uani 1 1 d . . . . .
C2 C 0.2867(4) -0.0604(3) 0.0689(2) 0.0380(6) Uani 1 1 d . . . . .
H2 H 0.197988 0.005549 0.066096 0.046 Uiso 1 1 calc R U . . .
C3 C 0.2499(4) -0.2211(4) 0.0135(2) 0.0431(7) Uani 1 1 d . . . . .
C4 C 0.3809(5) -0.3201(4) 0.0169(3) 0.0519(8) Uani 1 1 d . . . . .
H4 H 0.348023 -0.428080 -0.021058 0.062 Uiso 1 1 calc R U . . .
C5 C 0.5867(4) -0.1121(4) 0.1257(2) 0.0398(6) Uani 1 1 d . . . . .
C6 C 0.7322(4) 0.1249(4) 0.2319(2) 0.0439(7) Uani 1 1 d . . . . .
H6 H 0.825108 0.203857 0.277720 0.053 Uiso 1 1 calc R U . . .
C7 C 0.5589(4) 0.1478(3) 0.1985(2) 0.0379(6) Uani 1 1 d . . . . .
C8 C 0.9197(5) -0.0941(5) 0.1989(3) 0.0653(10) Uani 1 1 d . . . . .
H8A H 1.015834 -0.003975 0.218234 0.098 Uiso 1 1 calc R U . . .
H8B H 0.916974 -0.162639 0.132647 0.098 Uiso 1 1 calc R U . . .
H8C H 0.937799 -0.156746 0.252758 0.098 Uiso 1 1 calc R U . . .
C9 C 0.4808(4) 0.3000(4) 0.2273(2) 0.0426(7) Uani 1 1 d . . . . .
H9A H 0.455105 0.351918 0.167288 0.051 Uiso 1 1 calc R U . . .
H9B H 0.368439 0.269064 0.241176 0.051 Uiso 1 1 calc R U . . .
C10 C 0.6013(4) 0.4210(4) 0.3220(2) 0.0403(6) Uani 1 1 d . . . . .
C11 C 0.6847(4) 0.5719(4) 0.3245(3) 0.0464(7) Uani 1 1 d . . . . .
H11 H 0.676969 0.616401 0.265248 0.056 Uiso 1 1 calc R U . . .
C12 C 0.7651(4) 0.5474(4) 0.4913(2) 0.0429(7) Uani 1 1 d . . . . .
C13 C 0.6516(4) 0.4015(3) 0.4293(2) 0.0374(6) Uani 1 1 d . . . . .
C14 C 0.8802(6) 0.8146(5) 0.4613(4) 0.0729(12) Uani 1 1 d . . . . .
H14A H 0.873444 0.861551 0.530708 0.109 Uiso 1 1 calc R U . . .
H14B H 0.829065 0.879632 0.412729 0.109 Uiso 1 1 calc R U . . .
H14C H 1.003126 0.811967 0.463654 0.109 Uiso 1 1 calc R U . . .
C15 C 0.8011(5) 0.4623(4) 0.6430(3) 0.0541(8) Uani 1 1 d . . . . .
H15 H 0.851249 0.478212 0.715819 0.065 Uiso 1 1 calc R U . . .
C16 C 0.6891(4) 0.3171(4) 0.5901(2) 0.0472(7) Uani 1 1 d . . . . .
C17 C 0.6108(4) 0.2824(4) 0.4819(2) 0.0416(7) Uani 1 1 d . . . . .
H17 H 0.534953 0.184708 0.446334 0.050 Uiso 1 1 calc R U . . .


_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 C3 1.900(3) . ?
Br2 C16 1.906(3) . ?
N1 C5 1.334(4) . ?
N1 C4 1.342(4) . ?
N2 C5 1.364(4) . ?
N2 C6 1.384(4) . ?
N2 C8 1.453(4) . ?
N3 C12 1.355(4) . ?
N3 C11 1.381(4) . ?
N3 C14 1.444(4) . ?
N4 C15 1.330(5) . ?
N4 C12 1.336(4) . ?
C1 C2 1.387(4) . ?
C1 C5 1.412(4) . ?
C1 C7 1.427(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.383(5) . ?
C6 C7 1.358(4) . ?
C7 C9 1.505(4) . ?
C9 C10 1.496(4) . ?
C10 C11 1.360(4) . ?
C10 C13 1.433(4) . ?
C12 C13 1.416(4) . ?
C13 C17 1.387(4) . ?
C15 C16 1.379(5) . ?
C16 C17 1.379(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
C5 N1 C4 114.1(3) . . ?
C5 N2 C6 108.1(2) . . ?
C5 N2 C8 126.3(3) . . ?
C6 N2 C8 125.3(3) . . ?
C12 N3 C11 108.0(2) . . ?
C12 N3 C14 124.9(3) . . ?
C11 N3 C14 127.0(3) . . ?
C15 N4 C12 114.2(3) . . ?
C2 C1 C5 116.8(3) . . ?
C2 C1 C7 136.1(3) . . ?
C5 C1 C7 107.0(3) . . ?
C3 C2 C1 116.6(3) . . ?
C2 C3 C4 122.2(3) . . ?
C2 C3 Br1 119.3(2) . . ?
C4 C3 Br1 118.6(2) . . ?
N1 C4 C3 123.1(3) . . ?
N1 C5 N2 124.8(3) . . ?
N1 C5 C1 127.2(3) . . ?
N2 C5 C1 108.0(3) . . ?
C7 C6 N2 110.5(3) . . ?
C6 C7 C1 106.4(3) . . ?
C6 C7 C9 127.7(3) . . ?
C1 C7 C9 125.9(3) . . ?
C10 C9 C7 113.4(2) . . ?
C11 C10 C13 105.9(3) . . ?
C11 C10 C9 127.4(3) . . ?
C13 C10 C9 126.8(3) . . ?
C10 C11 N3 111.0(3) . . ?
N4 C12 N3 125.2(3) . . ?
N4 C12 C13 126.4(3) . . ?
N3 C12 C13 108.4(3) . . ?
C17 C13 C12 117.4(3) . . ?
C17 C13 C10 135.8(3) . . ?
C12 C13 C10 106.8(3) . . ?
N4 C15 C16 123.9(3) . . ?
C17 C16 C15 121.9(3) . . ?
C17 C16 Br2 119.8(2) . . ?
C15 C16 Br2 118.2(2) . . ?
C16 C17 C13 116.2(3) . . ?

_refine_diff_density_max         1.117
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.067

