# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_appp01_a
_database_code_depnum_ccdc_archive 'CCDC 2233103'
loop_
_audit_author_name
_audit_author_address
'Jayanta K. Nath'
;S B DEORAH COLLEGE ULUBARI GHY
India
;
_audit_update_record             
;
2022-12-28 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N2'
_chemical_formula_sum            'C18 H16 N2'
_chemical_formula_weight         260.33
_chemical_absolute_configuration ad

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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'

_cell_length_a                   6.607(2)
_cell_length_b                   10.064(2)
_cell_length_c                   21.600(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1436.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4197
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      19.23

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BROWN
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            44792
_diffrn_reflns_av_R_equivalents  0.1610
_diffrn_reflns_av_sigmaI/netI    0.0843
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         28.77
_reflns_number_total             3681
_reflns_number_gt                2145
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0400P)²+0.2277P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(5)
_refine_ls_number_reflns         3681
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1528
_refine_ls_wR_factor_gt          0.1339
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
N1 N 0.2279(4) 0.2385(3) 0.44888(11) 0.0689(7) Uani 1 1 d . . .
N2 N 0.5595(4) 0.6154(3) 0.25789(10) 0.0731(7) Uani 1 1 d . . .
C12 C 0.5407(4) 0.2615(2) 0.40876(10) 0.0483(6) Uani 1 1 d . . .
C4 C 0.7818(4) 0.6481(2) 0.33571(10) 0.0515(6) Uani 1 1 d . . .
C11 C 0.4709(4) 0.3904(3) 0.42905(10) 0.0525(6) Uani 1 1 d . . .
C3 C 0.6207(4) 0.5665(2) 0.35854(10) 0.0534(6) Uani 1 1 d . . .
C2 C 0.5948(4) 0.5179(3) 0.42522(10) 0.0550(6) Uani 1 1 d . . .
C17 C 0.3872(4) 0.1677(3) 0.42297(10) 0.0570(7) Uani 1 1 d . . .
C18 C 0.2810(5) 0.3714(3) 0.45347(12) 0.0638(7) Uani 1 1 d . . .
C13 C 0.7256(4) 0.2155(3) 0.38242(11) 0.0588(7) Uani 1 1 d . . .
C9 C 0.7397(4) 0.6787(3) 0.27222(10) 0.0566(6) Uani 1 1 d . . .
C10 C 0.4905(5) 0.5482(3) 0.30977(12) 0.0686(8) Uani 1 1 d . . .
C16 C 0.4122(6) 0.0314(3) 0.41211(13) 0.0710(8) Uani 1 1 d . . .
C5 C 0.9622(4) 0.6994(3) 0.36174(14) 0.0672(8) Uani 1 1 d . . .
C15 C 0.5919(6) -0.0100(4) 0.38644(13) 0.0753(9) Uani 1 1 d . . .
C8 C 0.8646(5) 0.7584(3) 0.23613(14) 0.0723(8) Uani 1 1 d . . .
C1 C 0.5030(7) 0.6296(4) 0.46626(14) 0.0776(10) Uani 1 1 d . . .
C14 C 0.7470(5) 0.0807(3) 0.37126(12) 0.0713(8) Uani 1 1 d . . .
C6 C 1.0870(6) 0.7790(4) 0.32547(17) 0.0855(10) Uani 1 1 d . . .
C7 C 1.0384(6) 0.8093(4) 0.26308(16) 0.0847(10) Uani 1 1 d . . .
H18 H 0.177(5) 0.444(4) 0.4729(15) 0.104(11) Uiso 1 1 d . . .
H13 H 0.835(4) 0.281(3) 0.3726(12) 0.068(8) Uiso 1 1 d . . .
H14 H 0.874(5) 0.045(3) 0.3520(14) 0.091(10) Uiso 1 1 d . . .
H2 H 0.737(4) 0.493(3) 0.4401(12) 0.064(7) Uiso 1 1 d . . .
H6 H 1.214(6) 0.809(4) 0.3433(19) 0.133(14) Uiso 1 1 d . . .
H7 H 1.138(5) 0.869(4) 0.2413(15) 0.100(11) Uiso 1 1 d . . .
H10 H 0.359(5) 0.499(3) 0.3074(15) 0.095(11) Uiso 1 1 d . . .
H1A H 0.362(5) 0.652(3) 0.4461(15) 0.087(10) Uiso 1 1 d . . .
H1B H 0.592(5) 0.706(3) 0.4634(13) 0.081(10) Uiso 1 1 d . . .
H1C H 0.469(5) 0.592(3) 0.5085(17) 0.098(10) Uiso 1 1 d . . .
H5 H 0.988(5) 0.684(3) 0.4060(16) 0.101(11) Uiso 1 1 d . . .
H15 H 0.621(5) -0.099(4) 0.3782(14) 0.086(10) Uiso 1 1 d . . .
H16 H 0.290(6) -0.026(4) 0.4250(17) 0.115(13) Uiso 1 1 d . . .
H2D H 0.495(7) 0.615(4) 0.219(2) 0.144(15) Uiso 1 1 d . . .
H1D H 0.113(6) 0.200(4) 0.4637(16) 0.114(13) Uiso 1 1 d . . .
H8 H 0.835(6) 0.780(4) 0.1903(19) 0.127(13) 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
N1 C17 1.383(4) . ?
N1 C18 1.389(4) . ?
N1 H1D 0.91(4) . ?
N2 C10 1.387(3) . ?
N2 C9 1.391(3) . ?
N2 H2D 0.95(4) . ?
C12 C13 1.420(3) . ?
C12 C17 1.425(3) . ?
C12 C11 1.441(3) . ?
C4 C5 1.421(4) . ?
C4 C9 1.433(3) . ?
C4 C3 1.436(3) . ?
C11 C18 1.375(4) . ?
C11 C2 1.530(4) . ?
C3 C10 1.376(4) . ?
C3 C2 1.530(3) . ?
C2 C1 1.549(4) . ?
C2 H2 1.02(3) . ?
C17 C16 1.400(4) . ?
C18 H18 1.08(4) . ?
C13 C14 1.383(4) . ?
C13 H13 1.00(3) . ?
C9 C8 1.393(4) . ?
C10 H10 1.01(3) . ?
C16 C15 1.370(5) . ?
C16 H16 1.04(4) . ?
C5 C6 1.394(5) . ?
C5 H5 0.98(3) . ?
C15 C14 1.416(5) . ?
C15 H15 0.93(3) . ?
C8 C7 1.391(5) . ?
C8 H8 1.03(4) . ?
C1 H1A 1.05(3) . ?
C1 H1B 0.97(3) . ?
C1 H1C 1.01(4) . ?
C14 H14 1.00(3) . ?
C6 C7 1.419(5) . ?
C6 H6 0.98(4) . ?
C7 H7 1.01(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
C17 N1 C18 109.1(3) . . ?
C17 N1 H1D 123(2) . . ?
C18 N1 H1D 127(2) . . ?
C10 N2 C9 109.2(2) . . ?
C10 N2 H2D 125(3) . . ?
C9 N2 H2D 126(3) . . ?
C13 C12 C17 118.9(2) . . ?
C13 C12 C11 133.0(2) . . ?
C17 C12 C11 108.0(2) . . ?
C5 C4 C9 117.7(2) . . ?
C5 C4 C3 134.5(2) . . ?
C9 C4 C3 107.8(2) . . ?
C18 C11 C12 106.0(2) . . ?
C18 C11 C2 129.2(3) . . ?
C12 C11 C2 124.7(2) . . ?
C10 C3 C4 106.4(2) . . ?
C10 C3 C2 127.4(2) . . ?
C4 C3 C2 126.1(2) . . ?
C11 C2 C3 112.29(19) . . ?
C11 C2 C1 111.7(3) . . ?
C3 C2 C1 110.5(2) . . ?
C11 C2 H2 105.7(15) . . ?
C3 C2 H2 105.8(14) . . ?
C1 C2 H2 110.6(15) . . ?
N1 C17 C16 130.9(3) . . ?
N1 C17 C12 106.7(2) . . ?
C16 C17 C12 122.4(3) . . ?
C11 C18 N1 110.2(3) . . ?
C11 C18 H18 129.0(19) . . ?
N1 C18 H18 120.8(19) . . ?
C14 C13 C12 118.0(3) . . ?
C14 C13 H13 122.6(16) . . ?
C12 C13 H13 119.5(16) . . ?
N2 C9 C8 130.7(3) . . ?
N2 C9 C4 106.4(2) . . ?
C8 C9 C4 122.9(3) . . ?
C3 C10 N2 110.2(3) . . ?
C3 C10 H10 130.6(19) . . ?
N2 C10 H10 119.2(19) . . ?
C15 C16 C17 117.3(3) . . ?
C15 C16 H16 128(2) . . ?
C17 C16 H16 115(2) . . ?
C6 C5 C4 119.2(3) . . ?
C6 C5 H5 122(2) . . ?
C4 C5 H5 118(2) . . ?
C16 C15 C14 121.7(3) . . ?
C16 C15 H15 123(2) . . ?
C14 C15 H15 116(2) . . ?
C7 C8 C9 118.2(3) . . ?
C7 C8 H8 119(2) . . ?
C9 C8 H8 123(2) . . ?
C2 C1 H1A 104.8(18) . . ?
C2 C1 H1B 107.6(19) . . ?
H1A C1 H1B 110(3) . . ?
C2 C1 H1C 109.2(19) . . ?
H1A C1 H1C 105(3) . . ?
H1B C1 H1C 119(2) . . ?
C13 C14 C15 121.6(3) . . ?
C13 C14 H14 120(2) . . ?
C15 C14 H14 118(2) . . ?
C5 C6 C7 121.5(3) . . ?
C5 C6 H6 118(3) . . ?
C7 C6 H6 120(3) . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 124.6(19) . . ?
C6 C7 H7 114.9(19) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        28.77
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_kkb_ap03_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2233142'
loop_
_audit_author_name
_audit_author_address
'Jayanta K. Nath'
;S B DEORAH COLLEGE ULUBARI GHY
India
;
_audit_update_record             
;
2022-12-28 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 Cl2 N2'
_chemical_formula_sum            'C18 H14 Cl2 N2'
_chemical_formula_weight         329.21


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'
Cl Cl 0.1484 0.1585 '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      MONOCLINIC
_space_group_IT_number           9
_space_group_name_H-M_alt        'I 1 c 1'
_space_group_name_Hall           'I -2yc'

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

_cell_length_a                   7.817(15)
_cell_length_b                   18.49(3)
_cell_length_c                   11.24(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.61(4)
_cell_angle_gamma                90.00
_cell_volume                     1614(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4036
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      22.44

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   'SADABS-2014/2 (Bruker,2014/2)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32008
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         28.42
_reflns_number_total             4036
_reflns_number_gt                3327
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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. 

DFIX 0.91 0.02 H2A N2
DFIX 0.91 0.02 H2A N2
DFIX 0.91 0.02 H2A N2
;

_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)+(0.0600P)²+0.6511P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_number_reflns         4036
_refine_ls_number_parameters     209
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1238
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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
Cl1 Cl 0.65711(12) 0.25730(4) 0.07795(11) 0.0760(3) Uani 1 1 d . . .
Cl2 Cl 1.23905(10) 0.21226(4) 0.69889(7) 0.0621(2) Uani 1 1 d . . .
N1 N 0.6353(3) -0.05984(14) 0.0733(3) 0.0547(6) Uani 1 1 d . . .
N2 N 1.1858(4) 0.03977(17) 0.2167(2) 0.0599(7) Uani 1 1 d D . .
C4 C 0.7500(4) -0.07466(15) 0.1745(3) 0.0500(7) Uani 1 1 d . . .
H4 H 0.7782 -0.1208 0.2033 0.060 Uiso 1 1 calc R . .
C5 C 0.6239(3) 0.01407(15) 0.0580(3) 0.0444(6) Uani 1 1 d . . .
C6 C 0.5250(3) 0.0555(2) -0.0294(3) 0.0538(7) Uani 1 1 d . . .
H6 H 0.4532 0.0336 -0.0908 0.065 Uiso 1 1 calc R . .
C7 C 0.5380(4) 0.1297(2) -0.0212(3) 0.0558(8) Uani 1 1 d . . .
H7 H 0.4743 0.1586 -0.0778 0.067 Uiso 1 1 calc R . .
C8 C 0.6473(3) 0.16231(15) 0.0727(3) 0.0472(6) Uani 1 1 d . . .
C9 C 0.7479(3) 0.12309(14) 0.1579(2) 0.0400(5) Uani 1 1 d . . .
H9 H 0.8214 0.1461 0.2170 0.048 Uiso 1 1 calc R . .
C10 C 0.7368(3) 0.04580(13) 0.1534(2) 0.0348(5) Uani 1 1 d . . .
C3 C 0.8162(3) -0.01151(13) 0.2260(2) 0.0383(5) Uani 1 1 d . . .
C2 C 0.9442(3) -0.00369(14) 0.3379(2) 0.0373(5) Uani 1 1 d . . .
H2 H 0.8847 0.0217 0.3976 0.045 Uiso 1 1 calc R . .
C1 C 0.9998(4) -0.07791(17) 0.3914(3) 0.0530(7) Uani 1 1 d . . .
H1A H 1.0674 -0.1028 0.3382 0.080 Uiso 1 1 calc R . .
H1B H 0.8994 -0.1061 0.4019 0.080 Uiso 1 1 calc R . .
H1C H 1.0672 -0.0711 0.4676 0.080 Uiso 1 1 calc R . .
C11 C 1.0970(3) 0.04221(13) 0.3150(2) 0.0356(5) Uani 1 1 d . . .
C18 C 1.1802(3) 0.09757(13) 0.3920(2) 0.0336(5) Uani 1 1 d . . .
C17 C 1.1550(3) 0.12424(13) 0.5061(2) 0.0358(5) Uani 1 1 d . . .
H17 H 1.0689 0.1057 0.5480 0.043 Uiso 1 1 calc R . .
C16 C 1.2625(3) 0.17901(13) 0.5539(3) 0.0423(6) Uani 1 1 d . . .
C15 C 1.3895(4) 0.21049(15) 0.4922(3) 0.0511(7) Uani 1 1 d . . .
H15 H 1.4549 0.2487 0.5267 0.061 Uiso 1 1 calc R . .
C14 C 1.4182(3) 0.18508(17) 0.3805(3) 0.0500(7) Uani 1 1 d . . .
H14 H 1.5018 0.2058 0.3387 0.060 Uiso 1 1 calc R . .
C13 C 1.3169(3) 0.12672(14) 0.3320(2) 0.0399(5) Uani 1 1 d . . .
C12 C 1.3176(3) 0.09016(15) 0.2260(2) 0.0380(5) Uani 1 1 d . . .
H12 H 1.3940 0.0979 0.1696 0.046 Uiso 1 1 calc R . .
H1 H 0.585(5) -0.0929(18) 0.022(3) 0.055(9) Uiso 1 1 d . . .
H2A H 1.159(6) 0.006(2) 0.154(3) 0.101(15) Uiso 1 1 d 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
Cl1 C8 1.759(4) . ?
Cl2 C16 1.771(4) . ?
N1 C5 1.379(4) . ?
N1 C4 1.392(5) . ?
N1 H1 0.90(4) . ?
N2 C11 1.372(4) . ?
N2 C12 1.384(4) . ?
N2 H2A 0.945(12) . ?
C4 C3 1.377(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(5) . ?
C5 C10 1.434(4) . ?
C6 C7 1.377(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.414(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(4) . ?
C9 C10 1.432(4) . ?
C9 H9 0.9300 . ?
C10 C3 1.434(4) . ?
C3 C2 1.521(4) . ?
C2 C11 1.511(4) . ?
C2 C1 1.541(4) . ?
C2 H2 0.9800 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C11 C18 1.445(4) . ?
C18 C17 1.409(4) . ?
C18 C13 1.434(4) . ?
C17 C16 1.384(4) . ?
C17 H17 0.9300 . ?
C16 C15 1.401(4) . ?
C15 C14 1.383(5) . ?
C15 H15 0.9300 . ?
C14 C13 1.411(4) . ?
C14 H14 0.9300 . ?
C13 C12 1.370(4) . ?
C12 H12 0.9300 . ?

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 108.8(2) . . ?
C5 N1 H1 125(2) . . ?
C4 N1 H1 126(2) . . ?
C11 N2 C12 111.0(3) . . ?
C11 N2 H2A 122(3) . . ?
C12 N2 H2A 127(3) . . ?
C3 C4 N1 110.6(3) . . ?
C3 C4 H4 124.7 . . ?
N1 C4 H4 124.7 . . ?
N1 C5 C6 130.5(3) . . ?
N1 C5 C10 106.7(2) . . ?
C6 C5 C10 122.8(3) . . ?
C7 C6 C5 117.8(3) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C8 120.5(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 122.9(3) . . ?
C9 C8 Cl1 119.0(2) . . ?
C7 C8 Cl1 118.1(2) . . ?
C8 C9 C10 118.3(2) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C9 C10 C5 117.7(2) . . ?
C9 C10 C3 134.2(2) . . ?
C5 C10 C3 108.2(2) . . ?
C4 C3 C10 105.7(3) . . ?
C4 C3 C2 127.4(3) . . ?
C10 C3 C2 126.9(2) . . ?
C11 C2 C3 111.8(2) . . ?
C11 C2 C1 111.9(2) . . ?
C3 C2 C1 111.6(2) . . ?
C11 C2 H2 107.1 . . ?
C3 C2 H2 107.1 . . ?
C1 C2 H2 107.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C11 C18 105.7(2) . . ?
N2 C11 C2 127.0(2) . . ?
C18 C11 C2 127.3(2) . . ?
C17 C18 C13 119.1(2) . . ?
C17 C18 C11 133.8(2) . . ?
C13 C18 C11 107.0(2) . . ?
C16 C17 C18 117.8(2) . . ?
C16 C17 H17 121.1 . . ?
C18 C17 H17 121.1 . . ?
C17 C16 C15 123.1(3) . . ?
C17 C16 Cl2 119.2(2) . . ?
C15 C16 Cl2 117.7(2) . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C14 C13 118.0(3) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C12 C13 C14 131.0(3) . . ?
C12 C13 C18 107.6(2) . . ?
C14 C13 C18 121.4(3) . . ?
C13 C12 N2 108.7(2) . . ?
C13 C12 H12 125.7 . . ?
N2 C12 H12 125.7 . . ?

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
C5 N1 C4 C3 -0.5(4) . . . . ?
C4 N1 C5 C6 -179.3(3) . . . . ?
C4 N1 C5 C10 0.3(3) . . . . ?
N1 C5 C6 C7 179.0(3) . . . . ?
C10 C5 C6 C7 -0.5(4) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C9 1.5(5) . . . . ?
C6 C7 C8 Cl1 -179.8(2) . . . . ?
C7 C8 C9 C10 -2.1(4) . . . . ?
Cl1 C8 C9 C10 179.16(18) . . . . ?
C8 C9 C10 C5 1.5(4) . . . . ?
C8 C9 C10 C3 -178.4(3) . . . . ?
N1 C5 C10 C9 -179.8(2) . . . . ?
C6 C5 C10 C9 -0.2(4) . . . . ?
N1 C5 C10 C3 0.1(3) . . . . ?
C6 C5 C10 C3 179.7(2) . . . . ?
N1 C4 C3 C10 0.6(3) . . . . ?
N1 C4 C3 C2 179.5(2) . . . . ?
C9 C10 C3 C4 179.5(3) . . . . ?
C5 C10 C3 C4 -0.4(3) . . . . ?
C9 C10 C3 C2 0.5(4) . . . . ?
C5 C10 C3 C2 -179.4(2) . . . . ?
C4 C3 C2 C11 127.1(3) . . . . ?
C10 C3 C2 C11 -54.1(3) . . . . ?
C4 C3 C2 C1 1.0(4) . . . . ?
C10 C3 C2 C1 179.7(2) . . . . ?
C12 N2 C11 C18 -0.6(3) . . . . ?
C12 N2 C11 C2 179.5(2) . . . . ?
C3 C2 C11 N2 -42.6(4) . . . . ?
C1 C2 C11 N2 83.4(3) . . . . ?
C3 C2 C11 C18 137.6(3) . . . . ?
C1 C2 C11 C18 -96.5(3) . . . . ?
N2 C11 C18 C17 -177.6(3) . . . . ?
C2 C11 C18 C17 2.3(4) . . . . ?
N2 C11 C18 C13 0.9(3) . . . . ?
C2 C11 C18 C13 -179.2(2) . . . . ?
C13 C18 C17 C16 1.4(3) . . . . ?
C11 C18 C17 C16 179.7(2) . . . . ?
C18 C17 C16 C15 2.5(4) . . . . ?
C18 C17 C16 Cl2 -178.20(17) . . . . ?
C17 C16 C15 C14 -3.0(4) . . . . ?
Cl2 C16 C15 C14 177.6(2) . . . . ?
C16 C15 C14 C13 -0.4(4) . . . . ?
C15 C14 C13 C12 -179.1(3) . . . . ?
C15 C14 C13 C18 4.3(4) . . . . ?
C17 C18 C13 C12 177.8(2) . . . . ?
C11 C18 C13 C12 -0.9(3) . . . . ?
C17 C18 C13 C14 -4.8(3) . . . . ?
C11 C18 C13 C14 176.4(2) . . . . ?
C14 C13 C12 N2 -176.5(3) . . . . ?
C18 C13 C12 N2 0.6(3) . . . . ?
C11 N2 C12 C13 0.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.42
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_app4_a
_database_code_depnum_ccdc_archive 'CCDC 2235034'
loop_
_audit_author_name
_audit_author_address
'Jayanta K. Nath'
;S B DEORAH COLLEGE ULUBARI GHY
India
;
_audit_update_record             
;
2023-01-08 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 Br2 N2'
_chemical_formula_sum            'C18 H14 Br2 N2'
_chemical_formula_weight         418.11

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 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   12.960(5)
_cell_length_b                   18.557(10)
_cell_length_c                   7.814(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.687(9)
_cell_angle_gamma                90.00
_cell_volume                     1616.2(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4496
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      19.23

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    5.013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.228
_exptl_absorpt_correction_T_max  0.332
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27969
_diffrn_reflns_av_R_equivalents  0.1464
_diffrn_reflns_av_sigmaI/netI    0.1514
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         28.23
_reflns_number_total             3876
_reflns_number_gt                2185
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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.

DFIX 0.90 0.02 H1 N1 
;

_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)+(0.0000P)²+2.1667P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_number_reflns         3876
_refine_ls_number_parameters     208
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1278
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.920
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.86700(7) 0.53637(5) 0.77964(9) 0.0512(3) Uani 1 1 d . . .
Br2 Br 0.23091(11) 0.49043(5) 0.73045(15) 0.0651(3) Uani 1 1 d . . .
C12 C 0.3141(6) 0.7050(4) 0.7289(10) 0.0266(15) Uani 1 1 d . . .
N1 N 0.3861(6) 0.6618(4) 0.2194(10) 0.0395(16) Uani 1 1 d D . .
C4 C 0.5496(6) 0.6529(4) 0.5214(10) 0.0248(14) Uani 1 1 d . . .
N2 N 0.2401(7) 0.8115(4) 0.7516(12) 0.0476(19) Uani 1 1 d . . .
C17 C 0.2229(8) 0.7390(4) 0.7497(11) 0.0348(18) Uani 1 1 d . . .
C9 C 0.4918(7) 0.6253(4) 0.3260(11) 0.0325(17) Uani 1 1 d . . .
C13 C 0.3163(7) 0.6302(4) 0.7236(10) 0.0319(17) Uani 1 1 d . . .
H13 H 0.3755 0.6062 0.7123 0.038 Uiso 1 1 calc R . .
C3 C 0.4753(6) 0.7071(4) 0.5305(10) 0.0286(15) Uani 1 1 d . . .
C5 C 0.6627(7) 0.6256(4) 0.6594(10) 0.0301(16) Uani 1 1 d . . .
H5 H 0.7048 0.6434 0.7887 0.036 Uiso 1 1 calc R . .
C2 C 0.4998(7) 0.7514(4) 0.7084(10) 0.0310(17) Uani 1 1 d . . .
H2 H 0.5584 0.7250 0.8273 0.037 Uiso 1 1 calc R . .
C6 C 0.7099(6) 0.5718(4) 0.5994(11) 0.0331(16) Uani 1 1 d . . .
C11 C 0.3879(6) 0.7609(4) 0.7215(10) 0.0311(17) Uani 1 1 d . . .
C18 C 0.3388(7) 0.8239(4) 0.7376(11) 0.041(2) Uani 1 1 d . . .
H18 H 0.3692 0.8694 0.7387 0.049 Uiso 1 1 calc R . .
C16 C 0.1336(8) 0.7010(6) 0.7571(12) 0.051(2) Uani 1 1 d . . .
H16 H 0.0729 0.7244 0.7656 0.061 Uiso 1 1 calc R . .
C7 C 0.6481(7) 0.5422(4) 0.4068(12) 0.0429(19) Uani 1 1 d . . .
H7 H 0.6819 0.5045 0.3736 0.051 Uiso 1 1 calc R . .
C10 C 0.3774(7) 0.7114(4) 0.3429(10) 0.038(2) Uani 1 1 d . . .
H10 H 0.3138 0.7432 0.3039 0.046 Uiso 1 1 calc R . .
C15 C 0.1385(8) 0.6258(5) 0.7511(11) 0.044(2) Uani 1 1 d . . .
H15 H 0.0810 0.5978 0.7576 0.053 Uiso 1 1 calc R . .
C8 C 0.5386(8) 0.5689(5) 0.2687(12) 0.041(2) Uani 1 1 d . . .
H8 H 0.4967 0.5501 0.1405 0.050 Uiso 1 1 calc R . .
C14 C 0.2299(9) 0.5931(4) 0.7353(12) 0.0394(18) Uani 1 1 d . . .
C1 C 0.5560(8) 0.8234(5) 0.7086(14) 0.048(2) Uani 1 1 d . . .
H1A H 0.6272 0.8153 0.7025 0.072 Uiso 1 1 calc R . .
H1B H 0.5763 0.8492 0.8283 0.072 Uiso 1 1 calc R . .
H1C H 0.4998 0.8511 0.5953 0.072 Uiso 1 1 calc R . .
H1 H 0.332(5) 0.653(4) 0.093(5) 0.04(2) Uiso 1 1 d D . .
H2A H 0.202(8) 0.845(5) 0.773(13) 0.05(3) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C6 1.906(7) . ?
Br2 C14 1.906(8) . ?
C12 C13 1.389(11) . ?
C12 C17 1.420(10) . ?
C12 C11 1.432(11) . ?
N1 C9 1.366(11) . ?
N1 C10 1.379(10) . ?
N1 H1 0.89(2) . ?
C4 C5 1.398(10) . ?
C4 C9 1.410(10) . ?
C4 C3 1.420(10) . ?
N2 H2A 0.86(10) . ?
N2 C18 1.358(12) . ?
N2 C17 1.363(11) . ?
N2 H2A 0.86(10) . ?
C17 C16 1.382(12) . ?
C9 C8 1.393(11) . ?
C13 C14 1.357(11) . ?
C13 H13 0.9300 . ?
C3 C10 1.366(10) . ?
C3 C2 1.503(9) . ?
C5 C6 1.373(10) . ?
C5 H5 0.9300 . ?
C2 C11 1.516(10) . ?
C2 C1 1.521(11) . ?
C2 H2 0.9800 . ?
C6 C7 1.406(10) . ?
C11 C18 1.366(10) . ?
C18 H18 0.9300 . ?
C16 C15 1.400(14) . ?
C16 H16 0.9300 . ?
C7 C8 1.364(12) . ?
C7 H7 0.9300 . ?
C10 H10 0.9300 . ?
C15 C14 1.391(12) . ?
C15 H15 0.9300 . ?
C8 H8 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C13 C12 C17 118.6(7) . . ?
C13 C12 C11 134.2(7) . . ?
C17 C12 C11 107.1(7) . . ?
C9 N1 C10 108.6(6) . . ?
C9 N1 H1 124(5) . . ?
C10 N1 H1 127(5) . . ?
C5 C4 C9 118.2(6) . . ?
C5 C4 C3 133.6(6) . . ?
C9 C4 C3 108.2(6) . . ?
H2A N2 C18 124(6) . . ?
H2A N2 C17 127(6) . . ?
C18 N2 C17 108.7(7) . . ?
H2A N2 H2A 0(10) . . ?
C18 N2 H2A 124(6) . . ?
C17 N2 H2A 127(6) . . ?
N2 C17 C16 129.7(8) . . ?
N2 C17 C12 107.4(8) . . ?
C16 C17 C12 122.8(7) . . ?
N1 C9 C8 130.0(7) . . ?
N1 C9 C4 107.1(6) . . ?
C8 C9 C4 122.9(7) . . ?
C14 C13 C12 118.3(7) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C10 C3 C4 105.6(6) . . ?
C10 C3 C2 127.1(7) . . ?
C4 C3 C2 127.3(6) . . ?
C6 C5 C4 118.3(6) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C3 C2 C11 111.6(6) . . ?
C3 C2 C1 110.9(6) . . ?
C11 C2 C1 111.8(6) . . ?
C3 C2 H2 107.4 . . ?
C11 C2 H2 107.4 . . ?
C1 C2 H2 107.4 . . ?
C5 C6 C7 122.7(7) . . ?
C5 C6 Br1 119.5(6) . . ?
C7 C6 Br1 117.8(6) . . ?
C18 C11 C12 105.3(7) . . ?
C18 C11 C2 127.7(7) . . ?
C12 C11 C2 126.9(6) . . ?
N2 C18 C11 111.4(7) . . ?
N2 C18 H18 124.3 . . ?
C11 C18 H18 124.3 . . ?
C17 C16 C15 117.0(8) . . ?
C17 C16 H16 121.5 . . ?
C15 C16 H16 121.5 . . ?
C8 C7 C6 119.9(7) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C3 C10 N1 110.5(7) . . ?
C3 C10 H10 124.8 . . ?
N1 C10 H10 124.8 . . ?
C14 C15 C16 119.5(8) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C7 C8 C9 117.8(7) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
C13 C14 C15 123.7(7) . . ?
C13 C14 Br2 119.4(7) . . ?
C15 C14 Br2 116.9(6) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        28.23
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.527
_refine_diff_density_min         -1.086
_refine_diff_density_rms         0.111

