# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ch16265
_database_code_depnum_ccdc_archive 'CCDC 1050602'
_audit_update_record             
;
2015-02-19 deposited with the CCDC.
2015-06-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 N2'
_chemical_formula_sum            'C20 H14 N2'
_chemical_formula_weight         282.33

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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                   4.5670(10)
_cell_length_b                   11.716(3)
_cell_length_c                   26.496(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1417.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9501
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8126
_diffrn_reflns_av_R_equivalents  0.0965
_diffrn_reflns_av_sigmaI/netI    0.1203
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2515
_reflns_number_gt                1427
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1093P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(9)
_refine_ls_number_reflns         2515
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1344
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.2262
_refine_ls_wR_factor_gt          0.1596
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9779(10) 0.1839(4) 0.91454(19) 0.0320(12) Uani 1 1 d . . .
C2 C 1.1130(12) 0.1638(4) 0.9616(2) 0.0414(14) Uani 1 1 d . . .
H2 H 1.0839 0.2160 0.9885 0.050 Uiso 1 1 calc R . .
C3 C 1.2844(12) 0.0703(4) 0.9686(2) 0.0466(14) Uani 1 1 d . . .
H3 H 1.3714 0.0571 1.0006 0.056 Uiso 1 1 calc R . .
C4 C 1.3344(13) -0.0073(5) 0.9290(2) 0.0535(17) Uani 1 1 d . . .
H4 H 1.4563 -0.0719 0.9342 0.064 Uiso 1 1 calc R . .
C5 C 1.2079(12) 0.0104(4) 0.8833(2) 0.0486(15) Uani 1 1 d . . .
H5 H 1.2417 -0.0426 0.8568 0.058 Uiso 1 1 calc R . .
C6 C 1.0279(11) 0.1057(4) 0.87442(19) 0.0375(13) Uani 1 1 d . . .
C7 C 0.8895(11) 0.1294(4) 0.8279(2) 0.0450(14) Uani 1 1 d . . .
H7 H 0.9179 0.0793 0.8002 0.054 Uiso 1 1 calc R . .
C8 C 0.7150(11) 0.2236(4) 0.82227(18) 0.0360(13) Uani 1 1 d . . .
C9 C 0.6807(11) 0.2975(4) 0.86516(17) 0.0318(12) Uani 1 1 d . . .
C10 C 0.4885(11) 0.3984(4) 0.86006(17) 0.0321(12) Uani 1 1 d . . .
C11 C 0.3869(10) 0.4343(4) 0.81158(17) 0.0359(13) Uani 1 1 d . . .
C12 C 0.5110(13) 0.3767(4) 0.76554(19) 0.0518(16) Uani 1 1 d . . .
H12A H 0.7032 0.4110 0.7572 0.062 Uiso 1 1 calc R . .
H12B H 0.3783 0.3892 0.7365 0.062 Uiso 1 1 calc R . .
C13 C 0.5486(13) 0.2491(5) 0.77437(19) 0.0480(15) Uani 1 1 d . . .
H13A H 0.3531 0.2128 0.7762 0.058 Uiso 1 1 calc R . .
H13B H 0.6544 0.2154 0.7454 0.058 Uiso 1 1 calc R . .
C14 C 0.3950(10) 0.4592(4) 0.90227(17) 0.0337(12) Uani 1 1 d . . .
H14 H 0.4578 0.4373 0.9350 0.040 Uiso 1 1 calc R . .
C15 C 0.2074(11) 0.5531(4) 0.89609(18) 0.0355(12) Uani 1 1 d . . .
C16 C 0.1117(13) 0.6215(4) 0.9371(2) 0.0455(14) Uani 1 1 d . . .
H16 H 0.1800 0.6055 0.9702 0.055 Uiso 1 1 calc R . .
C17 C -0.0762(13) 0.7095(4) 0.9294(2) 0.0509(16) Uani 1 1 d . . .
H17 H -0.1396 0.7544 0.9572 0.061 Uiso 1 1 calc R . .
C18 C -0.1774(14) 0.7343(5) 0.8807(2) 0.0550(17) Uani 1 1 d . . .
H18 H -0.3108 0.7955 0.8758 0.066 Uiso 1 1 calc R . .
C19 C -0.0874(11) 0.6720(4) 0.8404(2) 0.0472(15) Uani 1 1 d . . .
H19 H -0.1573 0.6906 0.8076 0.057 Uiso 1 1 calc R . .
C20 C 0.1094(11) 0.5798(4) 0.84664(19) 0.0387(13) Uani 1 1 d . . .
N1 N 0.8070(9) 0.2790(3) 0.90912(14) 0.0339(10) Uani 1 1 d . . .
N2 N 0.2027(9) 0.5204(4) 0.80482(16) 0.0414(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.368(6) . ?
C1 C2 1.410(7) . ?
C1 C6 1.422(6) . ?
C2 C3 1.359(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.406(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.359(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.412(7) . ?
C7 C8 1.369(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.438(6) . ?
C8 C13 1.510(7) . ?
C9 N1 1.318(5) . ?
C9 C10 1.478(6) . ?
C10 C14 1.393(6) . ?
C10 C11 1.429(6) . ?
C11 N2 1.326(6) . ?
C11 C12 1.505(6) . ?
C12 C13 1.523(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.404(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.419(7) . ?
C15 C20 1.419(6) . ?
C16 C17 1.357(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.402(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.357(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.416(6) . ?
C19 H19 0.9500 . ?
C20 N2 1.376(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
N1 C1 C2 118.6(4) . . ?
N1 C1 C6 122.6(5) . . ?
C2 C1 C6 118.8(4) . . ?
C3 C2 C1 120.5(5) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.8(5) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.9(5) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.2(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 124.3(5) . . ?
C5 C6 C1 118.8(5) . . ?
C7 C6 C1 117.0(4) . . ?
C8 C7 C6 121.0(5) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 117.6(5) . . ?
C7 C8 C13 123.0(5) . . ?
C9 C8 C13 119.4(4) . . ?
N1 C9 C8 123.5(4) . . ?
N1 C9 C10 118.2(4) . . ?
C8 C9 C10 118.3(4) . . ?
C14 C10 C11 118.1(4) . . ?
C14 C10 C9 121.2(4) . . ?
C11 C10 C9 120.7(4) . . ?
N2 C11 C10 123.5(4) . . ?
N2 C11 C12 118.1(4) . . ?
C10 C11 C12 118.3(4) . . ?
C11 C12 C13 111.0(4) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C8 C13 C12 112.4(4) . . ?
C8 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C8 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C10 C14 C15 119.6(4) . . ?
C10 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 122.7(5) . . ?
C14 C15 C20 118.2(5) . . ?
C16 C15 C20 119.1(5) . . ?
C17 C16 C15 120.6(5) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.3(5) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 120.9(5) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 120.7(5) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
N2 C20 C19 119.2(5) . . ?
N2 C20 C15 122.3(5) . . ?
C19 C20 C15 118.4(5) . . ?
C9 N1 C1 118.5(4) . . ?
C11 N2 C20 118.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.123
####################################################################### 
# 
# 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_a16933
_database_code_depnum_ccdc_archive 'CCDC 1052475'
_audit_update_record             
;
2015-03-06 deposited with the CCDC.
2015-06-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H13 Br N2'
_chemical_formula_sum            'C20 H13 Br N2'
_chemical_formula_weight         361.23

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P n'

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

_cell_length_a                   6.4502(5)
_cell_length_b                   10.8097(8)
_cell_length_c                   22.0781(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.457(4)
_cell_angle_gamma                90.00
_cell_volume                     1532.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    2.683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5774
_exptl_absorpt_correction_T_max  0.9239
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6473
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25.18
_reflns_number_total             3831
_reflns_number_gt                3197
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1379P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.19(3)
_refine_ls_number_reflns         3831
_refine_ls_number_parameters     391
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0747
_refine_ls_wR_factor_ref         0.1856
_refine_ls_wR_factor_gt          0.1724
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.004

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2574(18) 0.9489(10) 0.2501(5) 0.021(3) Uani 1 1 d . . .
H1 H 0.2729 1.0282 0.2733 0.026 Uiso 1 1 calc R . .
C2 C 0.3639(18) 0.9641(10) 0.1934(6) 0.022(3) Uani 1 1 d . . .
C3 C 0.6208(19) 1.0614(10) 0.1425(6) 0.0166(18) Uani 1 1 d . . .
C4 C 0.780(2) 1.1517(11) 0.1427(7) 0.024(2) Uani 1 1 d . . .
H4 H 0.8091 1.2074 0.1757 0.029 Uiso 1 1 calc R . .
C5 C 0.8963(19) 1.1536(12) 0.0883(6) 0.024(3) Uani 1 1 d . . .
H5 H 1.0073 1.2108 0.0865 0.029 Uiso 1 1 calc R . .
C6 C 0.851(3) 1.0788(14) 0.0429(9) 0.041(4) Uani 1 1 d . . .
H6 H 0.9273 1.0862 0.0085 0.049 Uiso 1 1 calc R . .
C7 C 0.704(2) 0.9931(12) 0.0416(6) 0.024(2) Uani 1 1 d . . .
H7 H 0.6858 0.9384 0.0079 0.029 Uiso 1 1 calc R . .
C8 C 0.5705(18) 0.9808(11) 0.0906(6) 0.0166(18) Uani 1 1 d . . .
C9 C 0.4096(18) 0.8958(11) 0.0928(6) 0.027(3) Uani 1 1 d . . .
H9 H 0.3782 0.8407 0.0597 0.033 Uiso 1 1 calc R . .
C10 C 0.2966(17) 0.8902(10) 0.1417(6) 0.024(3) Uani 1 1 d . . .
C11 C 0.1200(18) 0.8052(9) 0.1438(6) 0.021(3) Uani 1 1 d . . .
C12 C -0.0136(17) 0.8198(9) 0.1918(6) 0.018(3) Uani 1 1 d . . .
C13 C 0.0359(19) 0.9224(10) 0.2388(6) 0.0248(15) Uani 1 1 d . . .
H13A H -0.0378 0.9988 0.2245 0.030 Uiso 1 1 calc R . .
H13B H -0.0178 0.8977 0.2776 0.030 Uiso 1 1 calc R . .
C14 C -0.1840(18) 0.7461(11) 0.1904(6) 0.025(3) Uani 1 1 d . . .
H14 H -0.2749 0.7535 0.2216 0.030 Uiso 1 1 calc R . .
C15 C -0.2289(18) 0.6598(10) 0.1442(6) 0.014(2) Uani 1 1 d . . .
C16 C -0.402(2) 0.5817(12) 0.1402(7) 0.024(3) Uani 1 1 d . . .
H16 H -0.4963 0.5864 0.1706 0.029 Uiso 1 1 calc R . .
C17 C -0.4400(19) 0.4961(12) 0.0924(6) 0.024(3) Uani 1 1 d . . .
H17 H -0.5622 0.4466 0.0891 0.028 Uiso 1 1 calc R . .
C18 C -0.2884(19) 0.4855(13) 0.0484(6) 0.025(3) Uani 1 1 d . . .
H18 H -0.3035 0.4245 0.0173 0.030 Uiso 1 1 calc R . .
C19 C -0.127(3) 0.5629(11) 0.0526(8) 0.033(4) Uani 1 1 d . . .
H19 H -0.0325 0.5553 0.0224 0.040 Uiso 1 1 calc R . .
C20 C -0.0858(18) 0.6501(10) 0.0947(6) 0.017(3) Uani 1 1 d . . .
C21 C 0.2656(18) 0.3063(10) 0.2474(6) 0.026(3) Uani 1 1 d . . .
H21 H 0.2565 0.2267 0.2243 0.031 Uiso 1 1 calc R . .
C22 C 0.1593(17) 0.2910(10) 0.3033(6) 0.022(3) Uani 1 1 d . . .
C23 C -0.097(2) 0.1988(10) 0.3507(8) 0.029(3) Uani 1 1 d . . .
C24 C -0.263(2) 0.1107(11) 0.3526(7) 0.030(3) Uani 1 1 d . . .
H24 H -0.2806 0.0524 0.3203 0.036 Uiso 1 1 calc R . .
C25 C -0.385(2) 0.1040(12) 0.3931(6) 0.028(3) Uani 1 1 d . . .
H25 H -0.4936 0.0442 0.3895 0.033 Uiso 1 1 calc R . .
C26 C -0.365(2) 0.1895(10) 0.4482(7) 0.022(3) Uani 1 1 d . . .
H26 H -0.4565 0.1874 0.4793 0.026 Uiso 1 1 calc R . .
C27 C -0.195(2) 0.2721(12) 0.4483(7) 0.030(3) Uani 1 1 d . . .
H27 H -0.1664 0.3255 0.4823 0.036 Uiso 1 1 calc R . .
C28 C -0.072(2) 0.2785(11) 0.4022(7) 0.026(3) Uani 1 1 d . . .
C29 C 0.0969(16) 0.3617(11) 0.4032(5) 0.021(2) Uani 1 1 d . . .
H29 H 0.1295 0.4131 0.4377 0.026 Uiso 1 1 calc R . .
C30 C 0.2143(16) 0.3686(10) 0.3548(5) 0.021(2) Uani 1 1 d . . .
C31 C 0.3988(17) 0.4514(9) 0.3541(6) 0.017(2) Uani 1 1 d . . .
C32 C 0.536(2) 0.4386(10) 0.3071(6) 0.024(3) Uani 1 1 d . . .
C33 C 0.4919(18) 0.3427(11) 0.2593(6) 0.0248(15) Uani 1 1 d . . .
H33A H 0.5742 0.2679 0.2714 0.030 Uiso 1 1 calc R . .
H33B H 0.5404 0.3737 0.2209 0.030 Uiso 1 1 calc R . .
C34 C 0.7078(17) 0.5139(10) 0.3089(6) 0.023(3) Uani 1 1 d . . .
H34 H 0.7990 0.5093 0.2776 0.028 Uiso 1 1 calc R . .
C35 C 0.7495(19) 0.6003(11) 0.3586(7) 0.025(3) Uani 1 1 d . . .
C36 C 0.934(2) 0.6740(10) 0.3646(8) 0.031(3) Uani 1 1 d . . .
H36 H 1.0362 0.6673 0.3365 0.037 Uiso 1 1 calc R . .
C37 C 0.957(3) 0.7532(14) 0.4117(9) 0.047(3) Uani 1 1 d . . .
H37 H 1.0736 0.8076 0.4138 0.056 Uiso 1 1 calc R . .
C38 C 0.828(3) 0.7610(15) 0.4561(9) 0.047(3) Uani 1 1 d . . .
H38 H 0.8591 0.8161 0.4893 0.056 Uiso 1 1 calc R . .
C39 C 0.642(2) 0.6860(10) 0.4534(8) 0.027(3) Uani 1 1 d . . .
H39 H 0.5466 0.6893 0.4836 0.032 Uiso 1 1 calc R . .
C40 C 0.612(2) 0.6004(11) 0.3979(7) 0.027(3) Uani 1 1 d . . .
N1 N 0.5122(14) 1.0495(7) 0.1931(5) 0.023(2) Uani 1 1 d . . .
N2 N 0.0820(14) 0.7242(8) 0.0993(5) 0.022(2) Uani 1 1 d . . .
N3 N 0.0061(15) 0.2076(8) 0.3024(5) 0.026(2) Uani 1 1 d . . .
N4 N 0.4314(15) 0.5289(8) 0.4012(5) 0.027(2) Uani 1 1 d . . .
Br1 Br 0.40428(14) 0.81926(9) 0.29988(6) 0.0281(3) Uani 1 1 d . . .
Br2 Br 0.11407(13) 0.43734(10) 0.19688(6) 0.0280(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C13 1.455(17) . ?
C1 C2 1.493(16) . ?
C1 Br1 1.968(12) . ?
C1 H1 1.0000 . ?
C2 N1 1.329(14) . ?
C2 C10 1.427(16) . ?
C3 N1 1.380(16) . ?
C3 C4 1.414(17) . ?
C3 C8 1.452(17) . ?
C4 C5 1.477(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.30(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.32(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.451(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(17) . ?
C9 C10 1.359(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.467(16) . ?
C11 N2 1.321(15) . ?
C11 C12 1.436(17) . ?
C12 C14 1.356(16) . ?
C12 C13 1.532(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.393(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(17) . ?
C15 C20 1.499(16) . ?
C16 C17 1.41(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.447(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.330(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.334(19) . ?
C19 H19 0.9500 . ?
C20 N2 1.342(15) . ?
C21 C22 1.477(18) . ?
C21 C33 1.510(16) . ?
C21 Br2 2.000(11) . ?
C21 H21 1.0000 . ?
C22 N3 1.336(14) . ?
C22 C30 1.429(16) . ?
C23 N3 1.314(18) . ?
C23 C28 1.42(2) . ?
C23 C24 1.433(18) . ?
C24 C25 1.252(19) . ?
C24 H24 0.9500 . ?
C25 C26 1.523(19) . ?
C25 H25 0.9500 . ?
C26 C27 1.411(18) . ?
C26 H26 0.9500 . ?
C27 C28 1.351(19) . ?
C27 H27 0.9500 . ?
C28 C29 1.411(17) . ?
C29 C30 1.370(16) . ?
C29 H29 0.9500 . ?
C30 C31 1.490(15) . ?
C31 N4 1.335(15) . ?
C31 C32 1.432(17) . ?
C32 C34 1.374(17) . ?
C32 C33 1.487(17) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.448(19) . ?
C34 H34 0.9500 . ?
C35 C40 1.30(2) . ?
C35 C36 1.429(17) . ?
C36 C37 1.34(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.35(2) . ?
C37 H37 0.9500 . ?
C38 C39 1.44(2) . ?
C38 H38 0.9500 . ?
C39 C40 1.534(19) . ?
C39 H39 0.9500 . ?
C40 N4 1.404(17) . ?

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 C1 C2 113.7(11) . . ?
C13 C1 Br1 111.6(8) . . ?
C2 C1 Br1 108.2(8) . . ?
C13 C1 H1 107.7 . . ?
C2 C1 H1 107.7 . . ?
Br1 C1 H1 107.7 . . ?
N1 C2 C10 123.3(11) . . ?
N1 C2 C1 118.0(10) . . ?
C10 C2 C1 118.7(10) . . ?
N1 C3 C4 119.0(12) . . ?
N1 C3 C8 119.4(10) . . ?
C4 C3 C8 121.6(13) . . ?
C3 C4 C5 115.6(12) . . ?
C3 C4 H4 122.2 . . ?
C5 C4 H4 122.2 . . ?
C6 C5 C4 121.5(13) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 124.2(16) . . ?
C5 C6 H6 117.9 . . ?
C7 C6 H6 117.9 . . ?
C6 C7 C8 121.5(13) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 125.8(11) . . ?
C9 C8 C3 118.7(11) . . ?
C7 C8 C3 115.4(11) . . ?
C10 C9 C8 121.1(11) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C2 117.7(11) . . ?
C9 C10 C11 122.0(11) . . ?
C2 C10 C11 120.2(12) . . ?
N2 C11 C12 122.6(10) . . ?
N2 C11 C10 118.7(11) . . ?
C12 C11 C10 118.5(11) . . ?
C14 C12 C11 117.4(11) . . ?
C14 C12 C13 123.9(11) . . ?
C11 C12 C13 118.6(10) . . ?
C1 C13 C12 113.3(10) . . ?
C1 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C1 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C12 C14 C15 121.5(12) . . ?
C12 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 124.1(12) . . ?
C16 C15 C20 117.2(11) . . ?
C14 C15 C20 118.7(11) . . ?
C15 C16 C17 121.8(13) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C16 C17 C18 118.3(11) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C19 C18 C17 118.5(13) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C18 C19 C20 126.7(16) . . ?
C18 C19 H19 116.7 . . ?
C20 C19 H19 116.7 . . ?
N2 C20 C19 125.6(12) . . ?
N2 C20 C15 116.8(11) . . ?
C19 C20 C15 117.4(11) . . ?
C22 C21 C33 113.7(10) . . ?
C22 C21 Br2 107.7(8) . . ?
C33 C21 Br2 109.0(8) . . ?
C22 C21 H21 108.8 . . ?
C33 C21 H21 108.8 . . ?
Br2 C21 H21 108.8 . . ?
N3 C22 C30 122.4(11) . . ?
N3 C22 C21 117.6(10) . . ?
C30 C22 C21 119.9(10) . . ?
N3 C23 C28 125.2(12) . . ?
N3 C23 C24 120.5(14) . . ?
C28 C23 C24 114.1(14) . . ?
C25 C24 C23 125.6(14) . . ?
C25 C24 H24 117.2 . . ?
C23 C24 H24 117.2 . . ?
C24 C25 C26 121.5(12) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C27 C26 C25 113.3(13) . . ?
C27 C26 H26 123.4 . . ?
C25 C26 H26 123.4 . . ?
C28 C27 C26 122.7(13) . . ?
C28 C27 H27 118.6 . . ?
C26 C27 H27 118.6 . . ?
C27 C28 C23 122.7(12) . . ?
C27 C28 C29 121.9(12) . . ?
C23 C28 C29 115.3(12) . . ?
C30 C29 C28 120.4(11) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C22 118.3(10) . . ?
C29 C30 C31 122.8(10) . . ?
C22 C30 C31 118.9(10) . . ?
N4 C31 C32 124.2(10) . . ?
N4 C31 C30 115.9(11) . . ?
C32 C31 C30 119.8(10) . . ?
C34 C32 C31 118.3(11) . . ?
C34 C32 C33 122.1(12) . . ?
C31 C32 C33 119.6(11) . . ?
C32 C33 C21 114.9(10) . . ?
C32 C33 H33A 108.6 . . ?
C21 C33 H33A 108.6 . . ?
C32 C33 H33B 108.6 . . ?
C21 C33 H33B 108.6 . . ?
H33A C33 H33B 107.5 . . ?
C32 C34 C35 119.6(12) . . ?
C32 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C40 C35 C36 123.7(14) . . ?
C40 C35 C34 114.7(11) . . ?
C36 C35 C34 121.5(13) . . ?
C37 C36 C35 117.3(15) . . ?
C37 C36 H36 121.4 . . ?
C35 C36 H36 121.4 . . ?
C36 C37 C38 124.8(15) . . ?
C36 C37 H37 117.6 . . ?
C38 C37 H37 117.6 . . ?
C37 C38 C39 120.2(17) . . ?
C37 C38 H38 119.9 . . ?
C39 C38 H38 119.9 . . ?
C38 C39 C40 114.5(15) . . ?
C38 C39 H39 122.8 . . ?
C40 C39 H39 122.8 . . ?
C35 C40 N4 131.0(12) . . ?
C35 C40 C39 119.4(12) . . ?
N4 C40 C39 109.5(13) . . ?
C2 N1 C3 119.3(10) . . ?
C11 N2 C20 122.9(11) . . ?
C23 N3 C22 117.9(11) . . ?
C31 N4 C40 112.0(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
C13 C1 C2 N1 142.6(11) . . . . ?
Br1 C1 C2 N1 -92.9(10) . . . . ?
C13 C1 C2 C10 -35.0(15) . . . . ?
Br1 C1 C2 C10 89.5(11) . . . . ?
N1 C3 C4 C5 176.6(10) . . . . ?
C8 C3 C4 C5 -3.0(18) . . . . ?
C3 C4 C5 C6 1.7(19) . . . . ?
C4 C5 C6 C7 -2(2) . . . . ?
C5 C6 C7 C8 4(2) . . . . ?
C6 C7 C8 C9 178.5(14) . . . . ?
C6 C7 C8 C3 -4.9(19) . . . . ?
N1 C3 C8 C9 1.8(16) . . . . ?
C4 C3 C8 C9 -178.6(12) . . . . ?
N1 C3 C8 C7 -175.1(10) . . . . ?
C4 C3 C8 C7 4.5(17) . . . . ?
C7 C8 C9 C10 178.5(12) . . . . ?
C3 C8 C9 C10 2.0(17) . . . . ?
C8 C9 C10 C2 -7.2(17) . . . . ?
C8 C9 C10 C11 177.1(11) . . . . ?
N1 C2 C10 C9 9.4(17) . . . . ?
C1 C2 C10 C9 -173.1(11) . . . . ?
N1 C2 C10 C11 -174.8(10) . . . . ?
C1 C2 C10 C11 2.7(16) . . . . ?
C9 C10 C11 N2 6.2(16) . . . . ?
C2 C10 C11 N2 -169.4(10) . . . . ?
C9 C10 C11 C12 -169.2(11) . . . . ?
C2 C10 C11 C12 15.2(16) . . . . ?
N2 C11 C12 C14 0.2(17) . . . . ?
C10 C11 C12 C14 175.4(10) . . . . ?
N2 C11 C12 C13 -175.9(10) . . . . ?
C10 C11 C12 C13 -0.6(15) . . . . ?
C2 C1 C13 C12 47.9(14) . . . . ?
Br1 C1 C13 C12 -74.8(12) . . . . ?
C14 C12 C13 C1 153.1(12) . . . . ?
C11 C12 C13 C1 -31.1(15) . . . . ?
C11 C12 C14 C15 -0.2(18) . . . . ?
C13 C12 C14 C15 175.6(11) . . . . ?
C12 C14 C15 C16 -179.9(12) . . . . ?
C12 C14 C15 C20 -0.8(18) . . . . ?
C14 C15 C16 C17 179.9(12) . . . . ?
C20 C15 C16 C17 0.8(17) . . . . ?
C15 C16 C17 C18 3.4(18) . . . . ?
C16 C17 C18 C19 -4.7(18) . . . . ?
C17 C18 C19 C20 2(2) . . . . ?
C18 C19 C20 N2 177.3(13) . . . . ?
C18 C19 C20 C15 3(2) . . . . ?
C16 C15 C20 N2 -179.0(11) . . . . ?
C14 C15 C20 N2 1.9(16) . . . . ?
C16 C15 C20 C19 -3.8(16) . . . . ?
C14 C15 C20 C19 177.1(13) . . . . ?
C33 C21 C22 N3 -148.7(10) . . . . ?
Br2 C21 C22 N3 90.4(11) . . . . ?
C33 C21 C22 C30 34.6(15) . . . . ?
Br2 C21 C22 C30 -86.3(11) . . . . ?
N3 C23 C24 C25 -171.6(14) . . . . ?
C28 C23 C24 C25 3(2) . . . . ?
C23 C24 C25 C26 -2(2) . . . . ?
C24 C25 C26 C27 -1.0(19) . . . . ?
C25 C26 C27 C28 3.6(19) . . . . ?
C26 C27 C28 C23 -3(2) . . . . ?
C26 C27 C28 C29 -179.9(12) . . . . ?
N3 C23 C28 C27 174.0(13) . . . . ?
C24 C23 C28 C27 -0.7(19) . . . . ?
N3 C23 C28 C29 -9(2) . . . . ?
C24 C23 C28 C29 176.6(11) . . . . ?
C27 C28 C29 C30 -177.8(12) . . . . ?
C23 C28 C29 C30 4.8(17) . . . . ?
C28 C29 C30 C22 0.8(16) . . . . ?
C28 C29 C30 C31 -177.8(10) . . . . ?
N3 C22 C30 C29 -3.9(17) . . . . ?
C21 C22 C30 C29 172.7(10) . . . . ?
N3 C22 C30 C31 174.8(10) . . . . ?
C21 C22 C30 C31 -8.6(16) . . . . ?
C29 C30 C31 N4 -6.8(16) . . . . ?
C22 C30 C31 N4 174.6(10) . . . . ?
C29 C30 C31 C32 169.0(11) . . . . ?
C22 C30 C31 C32 -9.6(15) . . . . ?
N4 C31 C32 C34 -2.7(18) . . . . ?
C30 C31 C32 C34 -178.1(10) . . . . ?
N4 C31 C32 C33 175.5(11) . . . . ?
C30 C31 C32 C33 0.1(16) . . . . ?
C34 C32 C33 C21 -155.7(11) . . . . ?
C31 C32 C33 C21 26.2(16) . . . . ?
C22 C21 C33 C32 -42.6(14) . . . . ?
Br2 C21 C33 C32 77.6(12) . . . . ?
C31 C32 C34 C35 2.0(17) . . . . ?
C33 C32 C34 C35 -176.1(11) . . . . ?
C32 C34 C35 C40 -1.5(18) . . . . ?
C32 C34 C35 C36 175.5(11) . . . . ?
C40 C35 C36 C37 -4(2) . . . . ?
C34 C35 C36 C37 178.8(13) . . . . ?
C35 C36 C37 C38 5(2) . . . . ?
C36 C37 C38 C39 -4(3) . . . . ?
C37 C38 C39 C40 1(2) . . . . ?
C36 C35 C40 N4 -175.3(12) . . . . ?
C34 C35 C40 N4 2(2) . . . . ?
C36 C35 C40 C39 2(2) . . . . ?
C34 C35 C40 C39 178.6(11) . . . . ?
C38 C39 C40 C35 0.3(19) . . . . ?
C38 C39 C40 N4 177.8(12) . . . . ?
C10 C2 N1 C3 -5.7(17) . . . . ?
C1 C2 N1 C3 176.7(10) . . . . ?
C4 C3 N1 C2 -179.5(11) . . . . ?
C8 C3 N1 C2 0.1(15) . . . . ?
C12 C11 N2 C20 1.1(17) . . . . ?
C10 C11 N2 C20 -174.2(10) . . . . ?
C19 C20 N2 C11 -176.8(13) . . . . ?
C15 C20 N2 C11 -2.0(16) . . . . ?
C28 C23 N3 C22 6(2) . . . . ?
C24 C23 N3 C22 -179.7(12) . . . . ?
C30 C22 N3 C23 0.6(17) . . . . ?
C21 C22 N3 C23 -176.0(11) . . . . ?
C32 C31 N4 C40 2.5(16) . . . . ?
C30 C31 N4 C40 178.1(10) . . . . ?
C35 C40 N4 C31 -2(2) . . . . ?
C39 C40 N4 C31 -179.3(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.18
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         5.225
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.178
