# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_SawaTM347B
_database_code_depnum_ccdc_archive 'CCDC 2080098'
loop_
_audit_author_name
_audit_author_address
'Eri Ishikawa'
;Chubu University
Japan
;
_audit_update_record             
;
2021-04-26 deposited with the CCDC.	2021-09-01 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H10 F6 N2 O4'
_chemical_formula_moiety         'C12 H10 F6 N2 O4'
_chemical_formula_weight         360.21
_chemical_melting_point          328

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.449(5)
_cell_length_b                   10.164(8)
_cell_length_c                   11.085(6)
_cell_angle_alpha                115.47(2)
_cell_angle_beta                 98.08(2)
_cell_angle_gamma                92.02(3)
_cell_volume                     745.9(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4179
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      27.45
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364.00
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  0.967

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            7411
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_theta_max         27.462
_diffrn_reflns_theta_min         3.163
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3387
_reflns_number_gt                1618
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1356
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.2212
_refine_ls_wR_factor_gt          0.1853
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_reflns         3387
_refine_ls_number_parameters     257
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1140P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
F1 F 0.7482(4) 0.8771(3) 0.4856(3) 0.1334(11) Uani 1 1 d . . . . .
F2 F 1.0129(4) 0.8273(3) 0.4743(3) 0.1212(10) Uani 1 1 d . . . . .
F3 F 0.9328(5) 0.9341(3) 0.6647(2) 0.1273(11) Uani 1 1 d . . . . .
F4 F 0.6729(5) 0.0112(3) 0.1647(4) 0.1481(13) Uani 1 1 d . . . . .
F5 F 0.5643(5) 0.0798(3) 0.3433(3) 0.1412(13) Uani 1 1 d . . . . .
F6 F 0.4012(4) 0.0434(3) 0.1588(3) 0.1311(11) Uani 1 1 d . . . . .
O1 O 0.7861(6) 0.5855(3) 0.4207(2) 0.1414(16) Uani 1 1 d . . . . .
O2 O 0.8293(5) 0.6748(3) 0.6419(2) 0.1075(11) Uani 1 1 d . . . . .
O3 O 0.6811(5) 0.3352(3) 0.3800(2) 0.1088(12) Uani 1 1 d . . . . .
O4 O 0.5787(6) 0.2873(4) 0.1682(3) 0.1248(13) Uani 1 1 d . . . . .
N1 N 0.8724(3) 0.6931(3) 0.9960(2) 0.0571(7) Uani 1 1 d . . . . .
N2 N 0.7682(4) 0.5037(3) 0.7692(2) 0.0575(7) Uani 1 1 d . . . . .
C1 C 0.8670(5) 0.7001(4) 1.1244(3) 0.0631(9) Uani 1 1 d . . . . .
C2 C 0.7886(4) 0.5748(4) 1.1137(3) 0.0620(9) Uani 1 1 d . . . . .
C3 C 0.7383(4) 0.4787(3) 0.9713(3) 0.0531(7) Uani 1 1 d . . . . .
C4 C 0.6548(5) 0.3383(4) 0.8933(3) 0.0659(9) Uani 1 1 d . . . . .
C5 C 0.6335(5) 0.2831(5) 0.7531(4) 0.0711(9) Uani 1 1 d . . . . .
C6 C 0.6880(5) 0.3662(4) 0.6938(3) 0.0679(9) Uani 1 1 d . . . . .
C7 C 0.7955(4) 0.5599(3) 0.9051(3) 0.0490(7) Uani 1 1 d . . . . .
C8 C 0.9555(7) 0.8070(5) 0.9699(5) 0.0808(12) Uani 1 1 d . . . . .
C9 C 0.8257(5) 0.6825(4) 0.5364(3) 0.0663(9) Uani 1 1 d . . . . .
C10 C 0.8822(6) 0.8314(4) 0.5430(3) 0.0714(9) Uani 1 1 d . . . . .
C11 C 0.6107(5) 0.2536(4) 0.2582(3) 0.0681(9) Uani 1 1 d . . . . .
C12 C 0.5618(6) 0.0975(4) 0.2330(4) 0.0750(10) Uani 1 1 d . . . . .
H1 H 0.909(4) 0.779(4) 1.205(4) 0.067(9) Uiso 1 1 d . . . . .
H2 H 0.776(4) 0.549(4) 1.186(3) 0.063(9) Uiso 1 1 d . . . . .
H3 H 0.618(4) 0.283(4) 0.935(3) 0.068(9) Uiso 1 1 d . . . . .
H4 H 0.577(5) 0.195(5) 0.698(4) 0.080(12) Uiso 1 1 d . . . . .
H5 H 0.676(4) 0.332(4) 0.598(3) 0.070(9) Uiso 1 1 d . . . . .
H6 H 0.785(4) 0.551(3) 0.731(3) 0.046(8) Uiso 1 1 d . . . . .
H7 H 1.054(7) 0.777(6) 0.924(5) 0.126(18) Uiso 1 1 d . . . . .
H8 H 0.896(8) 0.833(6) 0.903(6) 0.15(2) Uiso 1 1 d . . . . .
H9 H 0.999(7) 0.889(7) 1.046(6) 0.136(19) Uiso 1 1 d . . . . .
H10 H 0.722(7) 0.430(7) 0.389(5) 0.137(18) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C10 1.314(4) . ?
F2 C10 1.309(4) . ?
F3 C10 1.292(4) . ?
F4 C12 1.298(5) . ?
F5 C12 1.308(4) . ?
F6 C12 1.303(4) . ?
O1 C9 1.221(4) . ?
O2 C9 1.202(3) . ?
O3 C11 1.262(4) . ?
O3 H10 0.96(6) . ?
O4 C11 1.185(4) . ?
N1 C7 1.337(4) . ?
N1 C1 1.400(4) . ?
N1 C8 1.448(5) . ?
N2 C7 1.343(4) . ?
N2 C6 1.343(5) . ?
N2 H6 0.78(3) . ?
C1 C2 1.333(5) . ?
C1 H1 0.91(4) . ?
C2 C3 1.439(4) . ?
C2 H2 0.95(3) . ?
C3 C4 1.376(5) . ?
C3 C7 1.409(4) . ?
C4 C5 1.389(5) . ?
C4 H3 0.93(4) . ?
C5 C6 1.357(5) . ?
C5 H4 0.88(4) . ?
C6 H5 0.96(3) . ?
C8 H7 0.94(5) . ?
C8 H8 0.95(6) . ?
C8 H9 0.90(6) . ?
C9 C10 1.524(5) . ?
C11 C12 1.508(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
C11 O3 H10 110(3) . . ?
C7 N1 C1 106.8(3) . . ?
C7 N1 C8 127.6(3) . . ?
C1 N1 C8 125.6(3) . . ?
C7 N2 C6 119.7(3) . . ?
C7 N2 H6 122(2) . . ?
C6 N2 H6 117(2) . . ?
C2 C1 N1 110.8(3) . . ?
C2 C1 H1 123(2) . . ?
N1 C1 H1 126(2) . . ?
C1 C2 C3 107.1(3) . . ?
C1 C2 H2 127(2) . . ?
C3 C2 H2 126(2) . . ?
C4 C3 C7 118.5(3) . . ?
C4 C3 C2 136.5(3) . . ?
C7 C3 C2 105.1(3) . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 H3 120(2) . . ?
C5 C4 H3 122(2) . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H4 117(2) . . ?
C4 C5 H4 122(2) . . ?
N2 C6 C5 120.9(3) . . ?
N2 C6 H5 115(2) . . ?
C5 C6 H5 124(2) . . ?
N1 C7 N2 128.3(3) . . ?
N1 C7 C3 110.3(2) . . ?
N2 C7 C3 121.4(3) . . ?
N1 C8 H7 112(3) . . ?
N1 C8 H8 121(4) . . ?
H7 C8 H8 92(4) . . ?
N1 C8 H9 113(3) . . ?
H7 C8 H9 106(5) . . ?
H8 C8 H9 110(5) . . ?
O2 C9 O1 129.1(3) . . ?
O2 C9 C10 117.6(3) . . ?
O1 C9 C10 113.3(3) . . ?
F3 C10 F2 107.8(3) . . ?
F3 C10 F1 106.4(3) . . ?
F2 C10 F1 103.5(3) . . ?
F3 C10 C9 114.2(3) . . ?
F2 C10 C9 112.8(3) . . ?
F1 C10 C9 111.4(3) . . ?
O4 C11 O3 127.5(4) . . ?
O4 C11 C12 119.8(3) . . ?
O3 C11 C12 112.7(3) . . ?
F4 C12 F6 104.6(4) . . ?
F4 C12 F5 106.6(4) . . ?
F6 C12 F5 107.2(3) . . ?
F4 C12 C11 111.2(3) . . ?
F6 C12 C11 112.4(3) . . ?
F5 C12 C11 114.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C1 C2 -0.1(4) . . . . ?
C8 N1 C1 C2 -176.9(4) . . . . ?
N1 C1 C2 C3 -0.2(4) . . . . ?
C1 C2 C3 C4 -179.7(4) . . . . ?
C1 C2 C3 C7 0.3(3) . . . . ?
C7 C3 C4 C5 0.9(5) . . . . ?
C2 C3 C4 C5 -179.0(3) . . . . ?
C3 C4 C5 C6 -2.1(5) . . . . ?
C7 N2 C6 C5 0.2(5) . . . . ?
C4 C5 C6 N2 1.5(6) . . . . ?
C1 N1 C7 N2 179.1(3) . . . . ?
C8 N1 C7 N2 -4.1(5) . . . . ?
C1 N1 C7 C3 0.3(3) . . . . ?
C8 N1 C7 C3 177.1(4) . . . . ?
C6 N2 C7 N1 180.0(3) . . . . ?
C6 N2 C7 C3 -1.3(4) . . . . ?
C4 C3 C7 N1 179.7(3) . . . . ?
C2 C3 C7 N1 -0.4(3) . . . . ?
C4 C3 C7 N2 0.7(4) . . . . ?
C2 C3 C7 N2 -179.3(3) . . . . ?
O2 C9 C10 F3 1.5(5) . . . . ?
O1 C9 C10 F3 -176.9(4) . . . . ?
O2 C9 C10 F2 125.1(4) . . . . ?
O1 C9 C10 F2 -53.4(5) . . . . ?
O2 C9 C10 F1 -119.0(4) . . . . ?
O1 C9 C10 F1 62.5(5) . . . . ?
O4 C11 C12 F4 74.0(5) . . . . ?
O3 C11 C12 F4 -107.2(4) . . . . ?
O4 C11 C12 F6 -42.8(5) . . . . ?
O3 C11 C12 F6 135.9(4) . . . . ?
O4 C11 C12 F5 -165.3(4) . . . . ?
O3 C11 C12 F5 13.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H10 O1 . . . 2.459(5) 0.99(7) 1.48(6) 170(5) no
N2 H6 O2 . . . 2.731(5) 0.80(4) 1.93(4) 178(2) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_SawaMari120C
_database_code_depnum_ccdc_archive 'CCDC 2080099'
loop_
_audit_author_name
_audit_author_address
'Eri Ishikawa'
;Chubu University
Japan
;
_audit_update_record             
;
2021-04-26 deposited with the CCDC.	2021-09-01 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C17 H15 Br N2'
_chemical_formula_moiety         'C17 H15 Br N2'
_chemical_formula_weight         327.22
_chemical_melting_point          405
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.928(5)
_cell_length_b                   17.983(10)
_cell_length_c                   9.771(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.34(2)
_cell_angle_gamma                90.0000
_cell_volume                     1566.1(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8141
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.36
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.800
_exptl_crystal_size_min          0.500
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664.00
_exptl_absorpt_coefficient_mu    2.624
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.188
_exptl_absorpt_correction_T_max  0.269

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            15324
_diffrn_reflns_av_unetI/netI     0.1017
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_theta_max         27.447
_diffrn_reflns_theta_min         3.005
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             7098
_reflns_number_gt                4128
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.989

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1400
_refine_ls_wR_factor_gt          0.1209
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         7098
_refine_ls_number_parameters     406
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0611P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(2)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1347 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(11)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.22693(10) 0.64980(6) 0.58275(11) 0.1059(4) Uani 1 1 d . . . . .
Br2 Br 0.99317(9) 0.36649(6) 0.75642(10) 0.0935(3) Uani 1 1 d . . . . .
N1 N 0.1806(6) 0.5460(3) 0.6422(6) 0.0604(13) Uani 1 1 d . . . . .
N2 N 0.3864(6) 0.5469(3) 0.4979(6) 0.0637(14) Uani 1 1 d . . . . .
H2A H 0.447896 0.519993 0.547556 0.076 Uiso 1 1 calc R U . . .
N3 N 0.3692(6) 0.4550(3) 0.8361(6) 0.0619(14) Uani 1 1 d . . . . .
H3A H 0.304071 0.479060 0.785131 0.074 Uiso 1 1 calc R U . . .
N4 N 0.5737(7) 0.4585(3) 0.6897(6) 0.0627(14) Uani 1 1 d . . . . .
C1 C 0.2825(8) 0.6635(4) 0.1926(7) 0.0630(16) Uani 1 1 d . . . . .
C2 C 0.4339(8) 0.6693(4) 0.1301(7) 0.0638(17) Uani 1 1 d . . . . .
C3 C 0.4630(11) 0.6291(4) 0.0172(9) 0.081(2) Uani 1 1 d . . . . .
C4 C 0.5991(12) 0.6312(6) -0.0430(11) 0.105(3) Uani 1 1 d . . . . .
H4A H 0.616441 0.602582 -0.119832 0.126 Uiso 1 1 calc R U . . .
C5 C 0.7064(14) 0.6766(7) 0.0144(15) 0.118(4) Uani 1 1 d . . . . .
H5A H 0.798066 0.680163 -0.025737 0.142 Uiso 1 1 calc R U . . .
C6 C 0.6841(11) 0.7166(6) 0.1276(14) 0.108(3) Uani 1 1 d . . . . .
H6A H 0.761285 0.746380 0.164746 0.129 Uiso 1 1 calc R U . . .
C7 C 0.5474(9) 0.7144(4) 0.1910(9) 0.076(2) Uani 1 1 d . . . . .
C8 C 0.5258(12) 0.7598(5) 0.3173(11) 0.101(3) Uani 1 1 d . . . . .
H8A H 0.426518 0.751821 0.347150 0.121 Uiso 1 1 calc R U . . .
H8B H 0.598243 0.745073 0.388656 0.121 Uiso 1 1 calc R U . . .
H8C H 0.538873 0.811530 0.296902 0.121 Uiso 1 1 calc R U . . .
C9 C 0.1601(10) 0.6375(6) 0.0909(8) 0.087(3) Uani 1 1 d . . . . .
C10 C 0.0916(11) 0.5742(7) 0.0910(9) 0.106(3) Uani 1 1 d . . . . .
H10A H 0.116686 0.539369 0.158899 0.127 Uiso 1 1 calc R U . . .
H10B H 0.017254 0.563495 0.023308 0.127 Uiso 1 1 calc R U . . .
C11 C 0.4147(9) 0.5782(4) 0.3737(7) 0.0650(17) Uani 1 1 d . . . . .
C12 C 0.2935(8) 0.6170(3) 0.3215(6) 0.0563(15) Uani 1 1 d . . . . .
C13 C 0.1824(8) 0.6102(3) 0.4211(6) 0.0522(14) Uani 1 1 d . . . . .
C14 C 0.0372(7) 0.6374(4) 0.4354(7) 0.0558(15) Uani 1 1 d . . . . .
C15 C -0.0302(8) 0.6176(3) 0.5540(7) 0.0583(16) Uani 1 1 d . . . . .
C16 C 0.0408(8) 0.5727(4) 0.6530(7) 0.0623(17) Uani 1 1 d . . . . .
C17 C 0.2466(7) 0.5654(3) 0.5287(6) 0.0523(14) Uani 1 1 d . . . . .
C18 C 0.4978(8) 0.3499(4) 1.1502(7) 0.0616(17) Uani 1 1 d . . . . .
H18 H 0.512810 0.297598 1.126773 0.074 Uiso 1 1 calc R U . . .
C19 C 0.6431(7) 0.3755(4) 1.2267(6) 0.0598(15) Uani 1 1 d . . . . .
C20 C 0.6838(9) 0.4502(5) 1.2235(8) 0.0714(19) Uani 1 1 d . . . . .
C21 C 0.8101(10) 0.4756(5) 1.2876(8) 0.087(2) Uani 1 1 d . . . . .
H21 H 0.831574 0.526202 1.286358 0.105 Uiso 1 1 calc R U . . .
C22 C 0.9068(11) 0.4282(7) 1.3544(10) 0.108(3) Uani 1 1 d . . . . .
H22 H 0.995961 0.445716 1.396552 0.129 Uiso 1 1 calc R U . . .
C23 C 0.8714(11) 0.3537(7) 1.3590(9) 0.104(3) Uani 1 1 d . . . . .
C24 C 0.7393(9) 0.3256(4) 1.2964(7) 0.073(2) Uani 1 1 d . . . . .
C25 C 0.7026(14) 0.2445(5) 1.3056(10) 0.111(3) Uani 1 1 d . . . . .
H25A H 0.782002 0.219337 1.357375 0.133 Uiso 1 1 calc R U . . .
H25B H 0.610452 0.238529 1.350415 0.133 Uiso 1 1 calc R U . . .
H25C H 0.691769 0.223757 1.215098 0.133 Uiso 1 1 calc R U . . .
C26 C 0.3644(10) 0.3520(7) 1.2367(9) 0.097(3) Uani 1 1 d . . . . .
H26 H 0.273582 0.340024 1.190419 0.117 Uiso 1 1 calc R U . . .
C27 C 0.3557(14) 0.3667(8) 1.3577(12) 0.127(4) Uani 1 1 d . . . . .
H27A H 0.441572 0.379190 1.411144 0.152 Uiso 1 1 calc R U . . .
H27B H 0.263088 0.365410 1.396651 0.152 Uiso 1 1 calc R U . . .
C28 C 0.3466(8) 0.4257(4) 0.9649(7) 0.0595(16) Uani 1 1 d . . . . .
C29 C 0.4723(8) 0.3907(3) 1.0159(7) 0.0570(16) Uani 1 1 d . . . . .
C30 C 0.5819(7) 0.3988(3) 0.9158(6) 0.0555(15) Uani 1 1 d . . . . .
C31 C 0.7281(7) 0.3767(4) 0.9030(7) 0.0603(16) Uani 1 1 d . . . . .
C32 C 0.7921(8) 0.3965(4) 0.7827(8) 0.0667(18) Uani 1 1 d . . . . .
C33 C 0.7148(9) 0.4364(4) 0.6793(8) 0.0678(18) Uani 1 1 d . . . . .
C34 C 0.5101(8) 0.4394(3) 0.8050(7) 0.0574(16) Uani 1 1 d . . . . .
H1 H 0.275(8) 0.713(5) 0.216(7) 0.07(2) Uiso 1 1 d . . . . .
H2 H 0.374(10) 0.597(5) -0.027(8) 0.10(3) Uiso 1 1 d . . . . .
H3 H 0.128(9) 0.665(4) -0.008(8) 0.09(2) Uiso 1 1 d . . . . .
H4 H 0.525(8) 0.571(4) 0.347(6) 0.058(17) Uiso 1 1 d . . . . .
H5 H -0.018(7) 0.672(3) 0.377(6) 0.043(15) Uiso 1 1 d . . . . .
H6 H -0.024(10) 0.571(6) 0.744(9) 0.11(3) Uiso 1 1 d . . . . .
H7 H 0.625(8) 0.480(4) 1.185(7) 0.06(2) Uiso 1 1 d . . . . .
H8 H 0.950(15) 0.316(7) 1.383(12) 0.15(4) Uiso 1 1 d . . . . .
H9 H 0.246(7) 0.430(3) 1.003(6) 0.052(16) Uiso 1 1 d . . . . .
H10 H 0.775(7) 0.348(3) 0.969(6) 0.052(17) Uiso 1 1 d . . . . .
H11 H 0.771(7) 0.452(4) 0.583(6) 0.063(19) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C15 1.887(7) . ?
Br2 C32 1.906(7) . ?
N1 C17 1.333(8) . ?
N1 C16 1.347(9) . ?
N2 C17 1.343(8) . ?
N2 C11 1.374(9) . ?
N2 H2A 0.8600 . ?
N3 C34 1.340(9) . ?
N3 C28 1.390(9) . ?
N3 H3A 0.8600 . ?
N4 C33 1.330(10) . ?
N4 C34 1.336(9) . ?
C1 C9 1.508(11) . ?
C1 C12 1.511(9) . ?
C1 C2 1.519(10) . ?
C1 H1 0.92(8) . ?
C2 C3 1.357(11) . ?
C2 C7 1.402(10) . ?
C3 C4 1.381(13) . ?
C3 H2 1.05(9) . ?
C4 C5 1.355(17) . ?
C4 H4A 0.9300 . ?
C5 C6 1.344(16) . ?
C5 H5A 0.9300 . ?
C6 C7 1.401(14) . ?
C6 H6A 0.9300 . ?
C7 C8 1.502(13) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.292(14) . ?
C9 H3 1.10(8) . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C11 C12 1.361(9) . ?
C11 H4 1.04(7) . ?
C12 C13 1.434(9) . ?
C13 C14 1.401(9) . ?
C13 C17 1.418(8) . ?
C14 C15 1.382(9) . ?
C14 H5 0.96(6) . ?
C15 C16 1.385(9) . ?
C16 H6 1.08(9) . ?
C18 C26 1.500(12) . ?
C18 C29 1.509(9) . ?
C18 C19 1.530(9) . ?
C18 H18 0.9800 . ?
C19 C24 1.392(9) . ?
C19 C20 1.391(11) . ?
C20 C21 1.339(11) . ?
C20 H7 0.83(7) . ?
C21 C22 1.353(13) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(16) . ?
C22 H22 0.9300 . ?
C23 C24 1.391(12) . ?
C23 H8 0.99(13) . ?
C24 C25 1.498(12) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.219(13) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9300 . ?
C27 H27B 0.9300 . ?
C28 C29 1.357(9) . ?
C28 H9 0.99(7) . ?
C29 C30 1.431(10) . ?
C30 C31 1.377(9) . ?
C30 C34 1.427(8) . ?
C31 C32 1.383(10) . ?
C31 H10 0.91(7) . ?
C32 C33 1.390(9) . ?
C33 H11 1.12(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 N1 C16 115.3(6) . . ?
C17 N2 C11 108.5(5) . . ?
C17 N2 H2A 125.8 . . ?
C11 N2 H2A 125.8 . . ?
C34 N3 C28 108.3(5) . . ?
C34 N3 H3A 125.9 . . ?
C28 N3 H3A 125.9 . . ?
C33 N4 C34 116.1(6) . . ?
C9 C1 C12 112.8(7) . . ?
C9 C1 C2 112.6(6) . . ?
C12 C1 C2 111.0(5) . . ?
C9 C1 H1 113(5) . . ?
C12 C1 H1 109(4) . . ?
C2 C1 H1 97(5) . . ?
C3 C2 C7 119.0(8) . . ?
C3 C2 C1 120.5(7) . . ?
C7 C2 C1 120.5(7) . . ?
C2 C3 C4 123.2(9) . . ?
C2 C3 H2 117(5) . . ?
C4 C3 H2 120(5) . . ?
C5 C4 C3 117.3(11) . . ?
C5 C4 H4A 121.4 . . ?
C3 C4 H4A 121.4 . . ?
C6 C5 C4 121.9(11) . . ?
C6 C5 H5A 119.1 . . ?
C4 C5 H5A 119.1 . . ?
C5 C6 C7 121.5(10) . . ?
C5 C6 H6A 119.2 . . ?
C7 C6 H6A 119.2 . . ?
C6 C7 C2 117.1(9) . . ?
C6 C7 C8 120.3(9) . . ?
C2 C7 C8 122.6(8) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C1 126.7(9) . . ?
C10 C9 H3 107(4) . . ?
C1 C9 H3 125(4) . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C12 C11 N2 111.0(7) . . ?
C12 C11 H4 136(4) . . ?
N2 C11 H4 113(3) . . ?
C11 C12 C13 105.6(6) . . ?
C11 C12 C1 127.4(7) . . ?
C13 C12 C1 126.8(6) . . ?
C14 C13 C17 117.4(6) . . ?
C14 C13 C12 135.9(6) . . ?
C17 C13 C12 106.6(6) . . ?
C15 C14 C13 116.3(6) . . ?
C15 C14 H5 116(4) . . ?
C13 C14 H5 128(4) . . ?
C14 C15 C16 122.2(6) . . ?
C14 C15 Br1 120.0(5) . . ?
C16 C15 Br1 117.8(5) . . ?
N1 C16 C15 122.8(7) . . ?
N1 C16 H6 127(5) . . ?
C15 C16 H6 110(5) . . ?
N1 C17 N2 125.6(6) . . ?
N1 C17 C13 125.9(6) . . ?
N2 C17 C13 108.4(6) . . ?
C26 C18 C29 113.2(6) . . ?
C26 C18 C19 113.3(6) . . ?
C29 C18 C19 111.1(6) . . ?
C26 C18 H18 106.2 . . ?
C29 C18 H18 106.2 . . ?
C19 C18 H18 106.2 . . ?
C24 C19 C20 118.6(7) . . ?
C24 C19 C18 121.8(7) . . ?
C20 C19 C18 119.6(6) . . ?
C21 C20 C19 122.2(8) . . ?
C21 C20 H7 119(5) . . ?
C19 C20 H7 119(5) . . ?
C20 C21 C22 120.5(9) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C23 119.2(8) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C22 C23 C24 122.0(9) . . ?
C22 C23 H8 120(7) . . ?
C24 C23 H8 115(7) . . ?
C19 C24 C23 117.6(8) . . ?
C19 C24 C25 121.7(7) . . ?
C23 C24 C25 120.7(8) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C18 130.5(10) . . ?
C27 C26 H26 114.8 . . ?
C18 C26 H26 114.8 . . ?
C26 C27 H27A 120.0 . . ?
C26 C27 H27B 120.0 . . ?
H27A C27 H27B 120.0 . . ?
C29 C28 N3 110.4(7) . . ?
C29 C28 H9 130(4) . . ?
N3 C28 H9 119(4) . . ?
C28 C29 C30 106.6(5) . . ?
C28 C29 C18 128.7(7) . . ?
C30 C29 C18 124.7(6) . . ?
C31 C30 C34 117.8(6) . . ?
C31 C30 C29 136.2(6) . . ?
C34 C30 C29 106.0(6) . . ?
C30 C31 C32 116.3(6) . . ?
C30 C31 H10 120(4) . . ?
C32 C31 H10 123(4) . . ?
C31 C32 C33 122.6(7) . . ?
C31 C32 Br2 118.7(5) . . ?
C33 C32 Br2 118.7(6) . . ?
N4 C33 C32 122.1(7) . . ?
N4 C33 H11 117(3) . . ?
C32 C33 H11 120(3) . . ?
N4 C34 N3 126.0(6) . . ?
N4 C34 C30 125.2(6) . . ?
N3 C34 C30 108.8(6) . . ?

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
C9 C1 C2 C3 -23.4(10) . . . . ?
C12 C1 C2 C3 104.0(7) . . . . ?
C9 C1 C2 C7 158.8(7) . . . . ?
C12 C1 C2 C7 -73.7(8) . . . . ?
C7 C2 C3 C4 -1.2(11) . . . . ?
C1 C2 C3 C4 -179.0(7) . . . . ?
C2 C3 C4 C5 -0.7(13) . . . . ?
C3 C4 C5 C6 1.9(15) . . . . ?
C4 C5 C6 C7 -1.1(15) . . . . ?
C5 C6 C7 C2 -0.8(12) . . . . ?
C5 C6 C7 C8 -179.9(8) . . . . ?
C3 C2 C7 C6 1.9(10) . . . . ?
C1 C2 C7 C6 179.7(6) . . . . ?
C3 C2 C7 C8 -179.0(7) . . . . ?
C1 C2 C7 C8 -1.2(10) . . . . ?
C12 C1 C9 C10 -15.6(13) . . . . ?
C2 C1 C9 C10 110.9(10) . . . . ?
C17 N2 C11 C12 -0.5(8) . . . . ?
N2 C11 C12 C13 0.8(8) . . . . ?
N2 C11 C12 C1 175.6(6) . . . . ?
C9 C1 C12 C11 121.5(8) . . . . ?
C2 C1 C12 C11 -5.9(10) . . . . ?
C9 C1 C12 C13 -64.8(9) . . . . ?
C2 C1 C12 C13 167.8(6) . . . . ?
C11 C12 C13 C14 177.5(7) . . . . ?
C1 C12 C13 C14 2.7(12) . . . . ?
C11 C12 C13 C17 -0.8(7) . . . . ?
C1 C12 C13 C17 -175.6(6) . . . . ?
C17 C13 C14 C15 -0.2(8) . . . . ?
C12 C13 C14 C15 -178.4(6) . . . . ?
C13 C14 C15 C16 -0.5(9) . . . . ?
C13 C14 C15 Br1 -179.0(5) . . . . ?
C17 N1 C16 C15 -0.2(9) . . . . ?
C14 C15 C16 N1 0.8(10) . . . . ?
Br1 C15 C16 N1 179.3(5) . . . . ?
C16 N1 C17 N2 178.2(6) . . . . ?
C16 N1 C17 C13 -0.6(9) . . . . ?
C11 N2 C17 N1 -179.0(6) . . . . ?
C11 N2 C17 C13 -0.1(7) . . . . ?
C14 C13 C17 N1 0.8(9) . . . . ?
C12 C13 C17 N1 179.5(6) . . . . ?
C14 C13 C17 N2 -178.1(5) . . . . ?
C12 C13 C17 N2 0.5(7) . . . . ?
C26 C18 C19 C24 91.4(9) . . . . ?
C29 C18 C19 C24 -139.9(7) . . . . ?
C26 C18 C19 C20 -90.8(8) . . . . ?
C29 C18 C19 C20 38.0(9) . . . . ?
C24 C19 C20 C21 -1.6(12) . . . . ?
C18 C19 C20 C21 -179.5(7) . . . . ?
C19 C20 C21 C22 2.6(14) . . . . ?
C20 C21 C22 C23 -2.0(15) . . . . ?
C21 C22 C23 C24 0.4(16) . . . . ?
C20 C19 C24 C23 0.0(11) . . . . ?
C18 C19 C24 C23 177.9(8) . . . . ?
C20 C19 C24 C25 179.4(8) . . . . ?
C18 C19 C24 C25 -2.8(11) . . . . ?
C22 C23 C24 C19 0.6(14) . . . . ?
C22 C23 C24 C25 -178.8(10) . . . . ?
C29 C18 C26 C27 -132.0(13) . . . . ?
C19 C18 C26 C27 -4.4(17) . . . . ?
C34 N3 C28 C29 -0.6(7) . . . . ?
N3 C28 C29 C30 0.8(7) . . . . ?
N3 C28 C29 C18 -178.7(6) . . . . ?
C26 C18 C29 C28 -1.9(10) . . . . ?
C19 C18 C29 C28 -130.7(7) . . . . ?
C26 C18 C29 C30 178.6(7) . . . . ?
C19 C18 C29 C30 49.8(8) . . . . ?
C28 C29 C30 C31 -179.4(7) . . . . ?
C18 C29 C30 C31 0.2(11) . . . . ?
C28 C29 C30 C34 -0.7(6) . . . . ?
C18 C29 C30 C34 178.9(5) . . . . ?
C34 C30 C31 C32 0.2(9) . . . . ?
C29 C30 C31 C32 178.8(6) . . . . ?
C30 C31 C32 C33 -0.1(10) . . . . ?
C30 C31 C32 Br2 -179.1(5) . . . . ?
C34 N4 C33 C32 -0.6(10) . . . . ?
C31 C32 C33 N4 0.2(11) . . . . ?
Br2 C32 C33 N4 179.2(6) . . . . ?
C33 N4 C34 N3 -179.2(7) . . . . ?
C33 N4 C34 C30 0.8(9) . . . . ?
C28 N3 C34 N4 -179.9(6) . . . . ?
C28 N3 C34 C30 0.1(7) . . . . ?
C31 C30 C34 N4 -0.6(9) . . . . ?
C29 C30 C34 N4 -179.6(6) . . . . ?
C31 C30 C34 N3 179.3(6) . . . . ?
C29 C30 C34 N3 0.4(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2A N4 . . . 2.911(8) 0.860 2.058 171.4 no
N3 H3A N1 . . . 2.955(8) 0.860 2.106 169.0 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
