# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_30714hm
_database_code_depnum_ccdc_archive 'CCDC 1485805'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Br N4'
_chemical_formula_sum            'C12 H9 Br N4'
_chemical_formula_weight         289.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   10.8827(2)
_cell_length_b                   7.0798(2)
_cell_length_c                   15.4121(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.5296(12)
_cell_angle_gamma                90.00
_cell_volume                     1167.47(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    10354
_cell_measurement_theta_min      4.13
_cell_measurement_theta_max      68.20

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    4.652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2577
_exptl_absorpt_correction_T_max  0.6534
_exptl_absorpt_process_details   
;Higashi, T. (1995). 
 Program for Absorption Correction.
 Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11758
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_sigmaI/netI    0.1017
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.13
_diffrn_reflns_theta_max         65.48
_reflns_number_total             3739
_reflns_number_gt                3186
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0300P)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   -0.03(3)
_refine_ls_number_reflns         3739
_refine_ls_number_parameters     307
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.038
_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 0.5161(5) -0.3482(12) 1.1764(4) 0.0389(17) Uani 1 1 d . . .
H1 H 0.5533 -0.3882 1.2341 0.047 Uiso 1 1 calc R . .
C2 C 0.5591(6) -0.2110(12) 1.1280(4) 0.045(2) Uani 1 1 d . . .
H2 H 0.6323 -0.1377 1.1464 0.054 Uiso 1 1 calc R . .
C3 C 0.4786(6) -0.1951(12) 1.0470(4) 0.0423(18) Uani 1 1 d . . .
H3 H 0.4880 -0.1113 1.0005 0.051 Uiso 1 1 calc R . .
C4 C 0.3832(5) -0.3225(11) 1.0464(3) 0.0314(15) Uani 1 1 d . . .
C5 C 0.2813(5) -0.3846(10) 0.9782(4) 0.0343(16) Uani 1 1 d . . .
C6 C 0.2480(5) -0.2989(10) 0.8982(3) 0.0341(16) Uani 1 1 d . . .
H4 H 0.2870 -0.1841 0.8863 0.041 Uiso 1 1 calc R . .
C7 C 0.1574(5) -0.3795(11) 0.8345(4) 0.0339(16) Uani 1 1 d . . .
C8 C 0.1355(5) -0.6090(10) 0.9328(4) 0.0350(16) Uani 1 1 d . . .
C9 C 0.1189(5) -0.3067(10) 0.7461(4) 0.0346(16) Uani 1 1 d . . .
C10 C 0.1661(6) -0.1667(12) 0.7011(3) 0.0386(15) Uani 1 1 d . . .
H5 H 0.2342 -0.0867 0.7247 0.046 Uiso 1 1 calc R . .
C11 C 0.0985(6) -0.1593(13) 0.6147(4) 0.0446(17) Uani 1 1 d . . .
H6 H 0.1117 -0.0754 0.5692 0.053 Uiso 1 1 calc R . .
C12 C 0.0095(6) -0.2973(11) 0.6090(4) 0.0409(18) Uani 1 1 d . . .
H7 H -0.0508 -0.3266 0.5580 0.049 Uiso 1 1 calc R . .
C13 C 0.8327(5) 0.2362(11) 0.7425(4) 0.0409(18) Uani 1 1 d . . .
H8 H 0.8664 0.2540 0.8032 0.049 Uiso 1 1 calc R . .
C14 C 0.8971(5) 0.1808(12) 0.6797(4) 0.0414(17) Uani 1 1 d . . .
H9 H 0.9838 0.1520 0.6888 0.050 Uiso 1 1 calc R . .
C15 C 0.8133(5) 0.1732(11) 0.5984(4) 0.0359(15) Uani 1 1 d . . .
H10 H 0.8327 0.1387 0.5428 0.043 Uiso 1 1 calc R . .
C16 C 0.6984(6) 0.2251(10) 0.6149(4) 0.0358(18) Uani 1 1 d . . .
C17 C 0.5743(5) 0.2362(9) 0.5598(4) 0.0292(14) Uani 1 1 d . . .
C18 C 0.5497(5) 0.2243(10) 0.4685(3) 0.0301(15) Uani 1 1 d . . .
H11 H 0.6160 0.2090 0.4366 0.036 Uiso 1 1 calc R . .
C19 C 0.4278(5) 0.2349(9) 0.4249(3) 0.0324(15) Uani 1 1 d . . .
C20 C 0.3674(5) 0.2762(9) 0.5557(3) 0.0318(15) Uani 1 1 d . . .
C21 C 0.3892(5) 0.2166(10) 0.3302(4) 0.0356(16) Uani 1 1 d . . .
C22 C 0.4495(6) 0.1581(11) 0.2647(3) 0.0363(15) Uani 1 1 d . . .
H12 H 0.5352 0.1243 0.2713 0.044 Uiso 1 1 calc R . .
C23 C 0.3606(6) 0.1570(11) 0.1850(4) 0.0409(17) Uani 1 1 d . . .
H13 H 0.3754 0.1203 0.1286 0.049 Uiso 1 1 calc R . .
C24 C 0.2501(6) 0.2183(11) 0.2044(4) 0.0414(18) Uani 1 1 d . . .
H14 H 0.1742 0.2331 0.1634 0.050 Uiso 1 1 calc R . .
Br1 Br 0.05531(7) -0.83565(12) 0.95963(5) 0.0596(3) Uani 1 1 d . . .
Br2 Br 0.23612(5) 0.32908(11) 0.62008(4) 0.0384(2) Uani 1 1 d . . .
N1 N 0.4089(4) -0.4176(8) 1.1260(3) 0.0366(14) Uani 1 1 d . . .
H15 H 0.3631 -0.5093 1.1420 0.044 Uiso 1 1 calc R . .
N2 N 0.2210(4) -0.5439(9) 0.9980(3) 0.0369(14) Uani 1 1 d . . .
N3 N 0.0973(4) -0.5429(8) 0.8526(3) 0.0352(14) Uani 1 1 d . . .
N4 N 0.0217(4) -0.3858(9) 0.6886(3) 0.0363(14) Uani 1 1 d . . .
H16 H -0.0255 -0.4791 0.7011 0.044 Uiso 1 1 calc R . .
N5 N 0.7114(4) 0.2620(8) 0.7034(3) 0.0333(13) Uani 1 1 d . . .
H17 H 0.6508 0.2969 0.7307 0.040 Uiso 1 1 calc R . .
N6 N 0.4789(4) 0.2641(7) 0.6062(3) 0.0299(12) Uani 1 1 d . . .
N7 N 0.3324(4) 0.2606(7) 0.4705(3) 0.0301(12) Uani 1 1 d . . .
N8 N 0.2667(4) 0.2544(8) 0.2916(3) 0.0350(13) Uani 1 1 d . . .
H18 H 0.2085 0.2956 0.3197 0.042 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.359(10) . ?
C1 N1 1.369(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.392(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(9) . ?
C3 H3 0.9500 . ?
C4 N1 1.382(7) . ?
C4 C5 1.451(7) . ?
C5 C6 1.362(8) . ?
C5 N2 1.367(8) . ?
C6 C7 1.382(8) . ?
C6 H4 0.9500 . ?
C7 N3 1.382(9) . ?
C7 C9 1.445(8) . ?
C8 N3 1.316(7) . ?
C8 N2 1.321(7) . ?
C8 Br1 1.908(7) . ?
C9 C10 1.363(10) . ?
C9 N4 1.369(7) . ?
C10 C11 1.400(8) . ?
C10 H5 0.9500 . ?
C11 C12 1.367(9) . ?
C11 H6 0.9500 . ?
C12 N4 1.362(7) . ?
C12 H7 0.9500 . ?
C13 C14 1.352(9) . ?
C13 N5 1.360(7) . ?
C13 H8 0.9500 . ?
C14 C15 1.410(7) . ?
C14 H9 0.9500 . ?
C15 C16 1.372(8) . ?
C15 H10 0.9500 . ?
C16 N5 1.371(6) . ?
C16 C17 1.460(8) . ?
C17 N6 1.378(7) . ?
C17 C18 1.386(7) . ?
C18 C19 1.376(7) . ?
C18 H11 0.9500 . ?
C19 N7 1.368(7) . ?
C19 C21 1.449(7) . ?
C20 N7 1.304(6) . ?
C20 N6 1.319(7) . ?
C20 Br2 1.919(6) . ?
C21 C22 1.365(8) . ?
C21 N8 1.383(7) . ?
C22 C23 1.417(7) . ?
C22 H12 0.9500 . ?
C23 C24 1.362(8) . ?
C23 H13 0.9500 . ?
C24 N8 1.347(7) . ?
C24 H14 0.9500 . ?
N1 H15 0.8800 . ?
N4 H16 0.8800 . ?
N5 H17 0.8800 . ?
N8 H18 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 106.7(5) . . ?
C2 C1 H1 126.6 . . ?
N1 C1 H1 126.6 . . ?
C1 C2 C3 109.1(6) . . ?
C1 C2 H2 125.4 . . ?
C3 C2 H2 125.4 . . ?
C4 C3 C2 107.6(6) . . ?
C4 C3 H3 126.2 . . ?
C2 C3 H3 126.2 . . ?
C3 C4 N1 106.5(5) . . ?
C3 C4 C5 132.8(5) . . ?
N1 C4 C5 120.0(6) . . ?
C6 C5 N2 120.7(6) . . ?
C6 C5 C4 124.2(6) . . ?
N2 C5 C4 115.0(5) . . ?
C5 C6 C7 119.8(7) . . ?
C5 C6 H4 120.1 . . ?
C7 C6 H4 120.1 . . ?
N3 C7 C6 120.3(6) . . ?
N3 C7 C9 115.0(6) . . ?
C6 C7 C9 124.7(7) . . ?
N3 C8 N2 130.4(6) . . ?
N3 C8 Br1 115.1(5) . . ?
N2 C8 Br1 114.5(4) . . ?
C10 C9 N4 106.7(5) . . ?
C10 C9 C7 131.9(6) . . ?
N4 C9 C7 121.4(6) . . ?
C9 C10 C11 109.2(7) . . ?
C9 C10 H5 125.4 . . ?
C11 C10 H5 125.4 . . ?
C12 C11 C10 106.2(6) . . ?
C12 C11 H6 126.9 . . ?
C10 C11 H6 126.9 . . ?
N4 C12 C11 108.6(5) . . ?
N4 C12 H7 125.7 . . ?
C11 C12 H7 125.7 . . ?
C14 C13 N5 108.1(5) . . ?
C14 C13 H8 125.9 . . ?
N5 C13 H8 125.9 . . ?
C13 C14 C15 108.2(6) . . ?
C13 C14 H9 125.9 . . ?
C15 C14 H9 125.9 . . ?
C16 C15 C14 106.7(5) . . ?
C16 C15 H10 126.6 . . ?
C14 C15 H10 126.6 . . ?
N5 C16 C15 107.7(5) . . ?
N5 C16 C17 119.0(5) . . ?
C15 C16 C17 133.2(6) . . ?
N6 C17 C18 120.8(5) . . ?
N6 C17 C16 114.2(5) . . ?
C18 C17 C16 125.0(5) . . ?
C19 C18 C17 118.9(5) . . ?
C19 C18 H11 120.6 . . ?
C17 C18 H11 120.6 . . ?
N7 C19 C18 120.7(5) . . ?
N7 C19 C21 115.0(5) . . ?
C18 C19 C21 124.3(5) . . ?
N7 C20 N6 131.1(5) . . ?
N7 C20 Br2 115.4(4) . . ?
N6 C20 Br2 113.5(4) . . ?
C22 C21 N8 107.2(5) . . ?
C22 C21 C19 133.0(5) . . ?
N8 C21 C19 119.7(5) . . ?
C21 C22 C23 107.3(6) . . ?
C21 C22 H12 126.3 . . ?
C23 C22 H12 126.3 . . ?
C24 C23 C22 107.4(5) . . ?
C24 C23 H13 126.3 . . ?
C22 C23 H13 126.3 . . ?
N8 C24 C23 108.4(5) . . ?
N8 C24 H14 125.8 . . ?
C23 C24 H14 125.8 . . ?
C1 N1 C4 110.0(5) . . ?
C1 N1 H15 125.0 . . ?
C4 N1 H15 125.0 . . ?
C8 N2 C5 114.7(5) . . ?
C8 N3 C7 114.1(5) . . ?
C12 N4 C9 109.4(6) . . ?
C12 N4 H16 125.3 . . ?
C9 N4 H16 125.3 . . ?
C13 N5 C16 109.3(5) . . ?
C13 N5 H17 125.4 . . ?
C16 N5 H17 125.4 . . ?
C20 N6 C17 113.7(5) . . ?
C20 N7 C19 114.8(5) . . ?
C24 N8 C21 109.6(5) . . ?
C24 N8 H18 125.2 . . ?
C21 N8 H18 125.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.2(8) . . . . ?
C1 C2 C3 C4 1.1(9) . . . . ?
C2 C3 C4 N1 -1.6(8) . . . . ?
C2 C3 C4 C5 -172.1(7) . . . . ?
C3 C4 C5 C6 -11.3(12) . . . . ?
N1 C4 C5 C6 179.2(6) . . . . ?
C3 C4 C5 N2 166.3(7) . . . . ?
N1 C4 C5 N2 -3.1(9) . . . . ?
N2 C5 C6 C7 -3.8(9) . . . . ?
C4 C5 C6 C7 173.7(6) . . . . ?
C5 C6 C7 N3 2.3(9) . . . . ?
C5 C6 C7 C9 -176.8(6) . . . . ?
N3 C7 C9 C10 -170.6(7) . . . . ?
C6 C7 C9 C10 8.6(11) . . . . ?
N3 C7 C9 N4 6.0(9) . . . . ?
C6 C7 C9 N4 -174.9(6) . . . . ?
N4 C9 C10 C11 -0.5(8) . . . . ?
C7 C9 C10 C11 176.4(7) . . . . ?
C9 C10 C11 C12 0.3(8) . . . . ?
C10 C11 C12 N4 0.1(8) . . . . ?
N5 C13 C14 C15 0.5(9) . . . . ?
C13 C14 C15 C16 -0.1(9) . . . . ?
C14 C15 C16 N5 -0.4(8) . . . . ?
C14 C15 C16 C17 -176.6(8) . . . . ?
N5 C16 C17 N6 -6.7(9) . . . . ?
C15 C16 C17 N6 169.2(7) . . . . ?
N5 C16 C17 C18 172.1(6) . . . . ?
C15 C16 C17 C18 -12.1(13) . . . . ?
N6 C17 C18 C19 -2.0(10) . . . . ?
C16 C17 C18 C19 179.3(6) . . . . ?
C17 C18 C19 N7 1.3(10) . . . . ?
C17 C18 C19 C21 -177.4(6) . . . . ?
N7 C19 C21 C22 -166.6(8) . . . . ?
C18 C19 C21 C22 12.2(13) . . . . ?
N7 C19 C21 N8 9.8(9) . . . . ?
C18 C19 C21 N8 -171.4(7) . . . . ?
N8 C21 C22 C23 -1.1(9) . . . . ?
C19 C21 C22 C23 175.6(7) . . . . ?
C21 C22 C23 C24 1.2(9) . . . . ?
C22 C23 C24 N8 -0.7(9) . . . . ?
C2 C1 N1 C4 -0.9(8) . . . . ?
C3 C4 N1 C1 1.6(8) . . . . ?
C5 C4 N1 C1 173.6(6) . . . . ?
N3 C8 N2 C5 -1.6(10) . . . . ?
Br1 C8 N2 C5 178.2(4) . . . . ?
C6 C5 N2 C8 3.3(9) . . . . ?
C4 C5 N2 C8 -174.4(5) . . . . ?
N2 C8 N3 C7 0.2(10) . . . . ?
Br1 C8 N3 C7 -179.5(4) . . . . ?
C6 C7 N3 C8 -0.5(8) . . . . ?
C9 C7 N3 C8 178.7(5) . . . . ?
C11 C12 N4 C9 -0.4(7) . . . . ?
C10 C9 N4 C12 0.5(7) . . . . ?
C7 C9 N4 C12 -176.8(6) . . . . ?
C14 C13 N5 C16 -0.7(9) . . . . ?
C15 C16 N5 C13 0.7(8) . . . . ?
C17 C16 N5 C13 177.5(6) . . . . ?
N7 C20 N6 C17 2.3(10) . . . . ?
Br2 C20 N6 C17 -176.7(4) . . . . ?
C18 C17 N6 C20 0.4(9) . . . . ?
C16 C17 N6 C20 179.2(6) . . . . ?
N6 C20 N7 C19 -3.0(11) . . . . ?
Br2 C20 N7 C19 176.0(4) . . . . ?
C18 C19 N7 C20 0.9(9) . . . . ?
C21 C19 N7 C20 179.7(6) . . . . ?
C23 C24 N8 C21 0.0(8) . . . . ?
C22 C21 N8 C24 0.7(8) . . . . ?
C19 C21 N8 C24 -176.5(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        65.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.085
####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1485806'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C12 H10 N4'
_chemical_formula_sum            'C12 H10 N4'
_chemical_formula_weight         210.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0041 0.0020 '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 0.0078 0.0041 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   13.2500(7)
_cell_length_b                   4.9503(3)
_cell_length_c                   15.2995(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.893(4)
_cell_angle_gamma                90
_cell_volume                     978.22(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4933
_cell_measurement_theta_min      2.536
_cell_measurement_theta_max      27.958

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.008
_exptl_crystal_size_min          0.008
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.999
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'ABSCOR (T.Higashi, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.78201
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'synchrotron radiation SPring-8 BL40XU'
_diffrn_radiation_monochromator  'Si(111) Channel Cut'
_diffrn_measurement_device_type  'Rigaku Saturn 724'
_diffrn_measurement_method       'Oscillation Photograph'
_diffrn_detector_area_resol_mean 29
_diffrn_reflns_number            4932
_diffrn_reflns_av_unetI/netI     0.0810
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.536
_diffrn_reflns_theta_max         27.958
_diffrn_reflns_theta_full        27.958
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             1728
_reflns_number_gt                1143
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Rapid Auto(Rigaku)'
_computing_cell_refinement       'Rapid Auto(Rigaku)'
_computing_data_reduction        'Rapid Auto(Rigaku)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+1.7128P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1728
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1866
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3551(2) -0.2205(7) 0.1197(2) 0.0220(8) Uani 1 1 d . . . . .
H1 H 0.3058 -0.3574 0.0975 0.026 Uiso 1 1 calc R U . . .
C2 C 0.4406(2) -0.1572(7) 0.0865(2) 0.0235(8) Uani 1 1 d . . . . .
H2 H 0.4612 -0.2424 0.0376 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4920(2) 0.0585(7) 0.1388(2) 0.0229(8) Uani 1 1 d . . . . .
H3 H 0.5534 0.1451 0.1310 0.027 Uiso 1 1 calc R U . . .
C4 C 0.4378(2) 0.1208(7) 0.2026(2) 0.0186(7) Uani 1 1 d . . . . .
C5 C 0.4538(2) 0.3215(7) 0.2733(2) 0.0189(7) Uani 1 1 d . . . . .
C6 C 0.5406(2) 0.4857(7) 0.2931(2) 0.0198(7) Uani 1 1 d . . . . .
H4 H 0.5933 0.4691 0.2603 0.024 Uiso 1 1 calc R U . . .
C7 C 0.5496(2) 0.6745(7) 0.3612(2) 0.0200(7) Uani 1 1 d . . . . .
C8 C 0.3961(3) 0.5264(8) 0.3862(2) 0.0279(9) Uani 1 1 d . . . . .
H5 H 0.3448 0.5381 0.4205 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6378(2) 0.8551(6) 0.3835(2) 0.0185(7) Uani 1 1 d . . . . .
C10 C 0.7225(2) 0.8794(7) 0.3459(2) 0.0248(8) Uani 1 1 d . . . . .
H6 H 0.7361 0.7747 0.2977 0.030 Uiso 1 1 calc R U . . .
C11 C 0.7853(2) 1.0872(7) 0.3915(2) 0.0255(8) Uani 1 1 d . . . . .
H7 H 0.8491 1.1480 0.3798 0.031 Uiso 1 1 calc R U . . .
C12 C 0.7378(2) 1.1862(7) 0.4560(2) 0.0239(8) Uani 1 1 d . . . . .
H8 H 0.7627 1.3290 0.4966 0.029 Uiso 1 1 calc R U . . .
N1 N 0.35357(19) -0.0537(6) 0.18934(18) 0.0218(7) Uani 1 1 d . . . . .
H9 H 0.3062 -0.0554 0.2216 0.026 Uiso 1 1 calc R U . . .
N2 N 0.64802(19) 1.0422(5) 0.45157(17) 0.0202(7) Uani 1 1 d . . . . .
H10 H 0.6042 1.0658 0.4865 0.024 Uiso 1 1 calc R U . . .
N3 N 0.3789(2) 0.3424(6) 0.32095(19) 0.0275(7) Uani 1 1 d . . . . .
N4 N 0.4756(2) 0.6963(6) 0.40973(18) 0.0235(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.352(4) . ?
C1 C2 1.377(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.415(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.370(4) . ?
C3 H3 0.9500 . ?
C4 N1 1.390(4) . ?
C4 C5 1.450(5) . ?
C5 N3 1.360(4) . ?
C5 C6 1.386(4) . ?
C6 C7 1.386(5) . ?
C6 H4 0.9500 . ?
C7 N4 1.359(4) . ?
C7 C9 1.451(4) . ?
C8 N4 1.332(4) . ?
C8 N3 1.333(4) . ?
C8 H5 0.9500 . ?
C9 C10 1.377(4) . ?
C9 N2 1.377(4) . ?
C10 C11 1.407(5) . ?
C10 H6 0.9500 . ?
C11 C12 1.374(5) . ?
C11 H7 0.9500 . ?
C12 N2 1.376(4) . ?
C12 H8 0.9500 . ?
N1 H9 0.8800 . ?
N2 H10 0.8800 . ?

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 108.1(3) . . ?
N1 C1 H1 126.0 . . ?
C2 C1 H1 126.0 . . ?
C1 C2 C3 107.1(3) . . ?
C1 C2 H2 126.4 . . ?
C3 C2 H2 126.4 . . ?
C4 C3 C2 108.1(3) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
C3 C4 N1 106.8(3) . . ?
C3 C4 C5 132.4(3) . . ?
N1 C4 C5 120.9(3) . . ?
N3 C5 C6 120.6(3) . . ?
N3 C5 C4 116.7(3) . . ?
C6 C5 C4 122.7(3) . . ?
C7 C6 C5 119.1(3) . . ?
C7 C6 H4 120.4 . . ?
C5 C6 H4 120.4 . . ?
N4 C7 C6 120.9(3) . . ?
N4 C7 C9 117.7(3) . . ?
C6 C7 C9 121.4(3) . . ?
N4 C8 N3 128.8(3) . . ?
N4 C8 H5 115.6 . . ?
N3 C8 H5 115.6 . . ?
C10 C9 N2 107.8(3) . . ?
C10 C9 C7 130.2(3) . . ?
N2 C9 C7 122.0(3) . . ?
C9 C10 C11 107.7(3) . . ?
C9 C10 H6 126.2 . . ?
C11 C10 H6 126.2 . . ?
C12 C11 C10 107.6(3) . . ?
C12 C11 H7 126.2 . . ?
C10 C11 H7 126.2 . . ?
C11 C12 N2 108.0(3) . . ?
C11 C12 H8 126.0 . . ?
N2 C12 H8 126.0 . . ?
C1 N1 C4 110.0(3) . . ?
C1 N1 H9 125.0 . . ?
C4 N1 H9 125.0 . . ?
C12 N2 C9 108.9(3) . . ?
C12 N2 H10 125.5 . . ?
C9 N2 H10 125.5 . . ?
C8 N3 C5 115.4(3) . . ?
C8 N4 C7 115.1(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
N1 C1 C2 C3 -0.3(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 N1 -0.3(4) . . . . ?
C2 C3 C4 C5 -179.9(3) . . . . ?
C3 C4 C5 N3 174.8(3) . . . . ?
N1 C4 C5 N3 -4.7(4) . . . . ?
C3 C4 C5 C6 -5.4(6) . . . . ?
N1 C4 C5 C6 175.1(3) . . . . ?
N3 C5 C6 C7 -0.9(5) . . . . ?
C4 C5 C6 C7 179.4(3) . . . . ?
C5 C6 C7 N4 1.3(5) . . . . ?
C5 C6 C7 C9 -178.8(3) . . . . ?
N4 C7 C9 C10 -179.4(3) . . . . ?
C6 C7 C9 C10 0.7(5) . . . . ?
N4 C7 C9 N2 0.4(5) . . . . ?
C6 C7 C9 N2 -179.5(3) . . . . ?
N2 C9 C10 C11 -0.4(4) . . . . ?
C7 C9 C10 C11 179.4(3) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C10 C11 C12 N2 0.6(4) . . . . ?
C2 C1 N1 C4 0.1(4) . . . . ?
C3 C4 N1 C1 0.2(4) . . . . ?
C5 C4 N1 C1 179.8(3) . . . . ?
C11 C12 N2 C9 -0.9(4) . . . . ?
C10 C9 N2 C12 0.8(4) . . . . ?
C7 C9 N2 C12 -179.0(3) . . . . ?
N4 C8 N3 C5 1.6(6) . . . . ?
C6 C5 N3 C8 -0.4(5) . . . . ?
C4 C5 N3 C8 179.3(3) . . . . ?
N3 C8 N4 C7 -1.2(5) . . . . ?
C6 C7 N4 C8 -0.4(5) . . . . ?
C9 C7 N4 C8 179.7(3) . . . . ?

_refine_diff_density_max         0.465
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_40521m
_database_code_depnum_ccdc_archive 'CCDC 1485807'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H17 Br N4'
_chemical_formula_sum            'C24 H17 Br N4'
_chemical_formula_weight         441.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   13.262(5)
_cell_length_b                   5.685(2)
_cell_length_c                   25.480(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.5060(10)
_cell_angle_gamma                90.00
_cell_volume                     1882.4(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    2055
_cell_measurement_theta_min      25.4
_cell_measurement_theta_max      68.3

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    3.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5344
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12125
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         6.81
_diffrn_reflns_theta_max         65.99
_reflns_number_total             3228
_reflns_number_gt                3130
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0349P)²+0.8291P] 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_number_reflns         3228
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0215
_refine_ls_wR_factor_ref         0.0575
_refine_ls_wR_factor_gt          0.0569
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.21168(10) 0.4494(2) 0.04230(5) 0.0150(3) Uani 1 1 d . . .
H1 H 0.1888 0.3106 0.0498 0.018 Uiso 1 1 calc R . .
N2 N 0.30176(9) 0.2834(2) 0.14383(5) 0.0165(3) Uani 1 1 d . . .
N3 N 0.43271(9) 0.2991(2) 0.22392(5) 0.0149(3) Uani 1 1 d . . .
N4 N 0.61109(9) 0.4843(2) 0.28495(5) 0.0140(3) Uani 1 1 d . . .
H2 H 0.5934 0.3468 0.2962 0.017 Uiso 1 1 calc R . .
C1 C 0.09353(11) 0.4907(3) -0.04679(6) 0.0148(3) Uani 1 1 d . . .
C2 C 0.06801(12) 0.6267(3) -0.09349(6) 0.0190(3) Uani 1 1 d . . .
H3 H 0.1013 0.7735 -0.0955 0.023 Uiso 1 1 calc R . .
C3 C -0.00519(13) 0.5499(3) -0.13675(6) 0.0234(4) Uani 1 1 d . . .
H4 H -0.0214 0.6433 -0.1682 0.028 Uiso 1 1 calc R . .
C4 C -0.05502(12) 0.3361(3) -0.13416(6) 0.0229(4) Uani 1 1 d . . .
H5 H -0.1049 0.2826 -0.1638 0.028 Uiso 1 1 calc R . .
C5 C -0.03135(12) 0.2017(3) -0.08788(6) 0.0209(3) Uani 1 1 d . . .
H6 H -0.0657 0.0564 -0.0858 0.025 Uiso 1 1 calc R . .
C6 C 0.04218(11) 0.2779(3) -0.04466(6) 0.0171(3) Uani 1 1 d . . .
H7 H 0.0578 0.1841 -0.0132 0.020 Uiso 1 1 calc R . .
C7 C 0.17456(12) 0.5759(3) -0.00321(6) 0.0149(3) Uani 1 1 d . . .
C8 C 0.23057(11) 0.7832(3) 0.00036(6) 0.0173(3) Uani 1 1 d . . .
H8 H 0.2219 0.9056 -0.0255 0.021 Uiso 1 1 calc R . .
C9 C 0.30230(11) 0.7805(3) 0.04899(6) 0.0187(3) Uani 1 1 d . . .
H9 H 0.3506 0.9007 0.0620 0.022 Uiso 1 1 calc R . .
C10 C 0.28981(11) 0.5708(3) 0.07456(6) 0.0162(3) Uani 1 1 d . . .
C11 C 0.34233(12) 0.4789(3) 0.12571(6) 0.0157(3) Uani 1 1 d . . .
C12 C 0.42927(11) 0.5883(3) 0.15529(6) 0.0165(3) Uani 1 1 d . . .
H10 H 0.4583 0.7229 0.1419 0.020 Uiso 1 1 calc R . .
C13 C 0.47230(11) 0.4944(3) 0.20511(6) 0.0154(3) Uani 1 1 d . . .
C14 C 0.35049(11) 0.2120(3) 0.19161(6) 0.0155(3) Uani 1 1 d . . .
C15 C 0.56042(11) 0.5989(3) 0.23975(6) 0.0151(3) Uani 1 1 d . . .
C16 C 0.60999(11) 0.8108(3) 0.23667(6) 0.0162(3) Uani 1 1 d . . .
H11 H 0.5913 0.9276 0.2098 0.019 Uiso 1 1 calc R . .
C17 C 0.69297(11) 0.8220(3) 0.28037(5) 0.0153(3) Uani 1 1 d . . .
H12 H 0.7406 0.9480 0.2884 0.018 Uiso 1 1 calc R . .
C18 C 0.69320(11) 0.6167(3) 0.30988(6) 0.0136(3) Uani 1 1 d . . .
C19 C 0.76733(11) 0.5346(3) 0.35654(6) 0.0140(3) Uani 1 1 d . . .
C20 C 0.75552(11) 0.3218(3) 0.38210(6) 0.0152(3) Uani 1 1 d . . .
H13 H 0.6951 0.2308 0.3706 0.018 Uiso 1 1 calc R . .
C21 C 0.83126(12) 0.2416(3) 0.42413(6) 0.0175(3) Uani 1 1 d . . .
H14 H 0.8222 0.0965 0.4411 0.021 Uiso 1 1 calc R . .
C22 C 0.91998(12) 0.3724(3) 0.44141(6) 0.0190(3) Uani 1 1 d . . .
H15 H 0.9723 0.3159 0.4696 0.023 Uiso 1 1 calc R . .
C23 C 0.93166(12) 0.5873(3) 0.41700(6) 0.0190(3) Uani 1 1 d . . .
H16 H 0.9916 0.6791 0.4291 0.023 Uiso 1 1 calc R . .
C24 C 0.85647(11) 0.6676(3) 0.37519(6) 0.0159(3) Uani 1 1 d . . .
H17 H 0.8653 0.8145 0.3589 0.019 Uiso 1 1 calc R . .
Br1 Br 0.291836(11) -0.05199(3) 0.220183(6) 0.01849(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.370(2) . ?
N1 C10 1.373(2) . ?
N1 H1 0.8800 . ?
N2 C14 1.323(2) . ?
N2 C11 1.355(2) . ?
N3 C14 1.3245(19) . ?
N3 C13 1.356(2) . ?
N4 C18 1.371(2) . ?
N4 C15 1.376(2) . ?
N4 H2 0.8800 . ?
C1 C6 1.394(2) . ?
C1 C2 1.403(2) . ?
C1 C7 1.465(2) . ?
C2 C3 1.386(2) . ?
C2 H3 0.9500 . ?
C3 C4 1.391(3) . ?
C3 H4 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H5 0.9500 . ?
C5 C6 1.387(2) . ?
C5 H6 0.9500 . ?
C6 H7 0.9500 . ?
C7 C8 1.386(2) . ?
C8 C9 1.404(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.447(2) . ?
C11 C12 1.392(2) . ?
C12 C13 1.390(2) . ?
C12 H10 0.9500 . ?
C13 C15 1.444(2) . ?
C14 Br1 1.9007(16) . ?
C15 C16 1.382(2) . ?
C16 C17 1.402(2) . ?
C16 H11 0.9500 . ?
C17 C18 1.388(2) . ?
C17 H12 0.9500 . ?
C18 C19 1.460(2) . ?
C19 C20 1.398(2) . ?
C19 C24 1.404(2) . ?
C20 C21 1.391(2) . ?
C20 H13 0.9500 . ?
C21 C22 1.387(2) . ?
C21 H14 0.9500 . ?
C22 C23 1.393(2) . ?
C22 H15 0.9500 . ?
C23 C24 1.383(2) . ?
C23 H16 0.9500 . ?
C24 H17 0.9500 . ?

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
C7 N1 C10 110.11(13) . . ?
C7 N1 H1 124.9 . . ?
C10 N1 H1 124.9 . . ?
C14 N2 C11 114.27(13) . . ?
C14 N3 C13 114.54(13) . . ?
C18 N4 C15 109.77(13) . . ?
C18 N4 H2 125.1 . . ?
C15 N4 H2 125.1 . . ?
C6 C1 C2 118.31(14) . . ?
C6 C1 C7 123.19(14) . . ?
C2 C1 C7 118.48(14) . . ?
C3 C2 C1 120.85(15) . . ?
C3 C2 H3 119.6 . . ?
C1 C2 H3 119.6 . . ?
C2 C3 C4 120.11(15) . . ?
C2 C3 H4 119.9 . . ?
C4 C3 H4 119.9 . . ?
C5 C4 C3 119.50(15) . . ?
C5 C4 H5 120.2 . . ?
C3 C4 H5 120.2 . . ?
C6 C5 C4 120.44(16) . . ?
C6 C5 H6 119.8 . . ?
C4 C5 H6 119.8 . . ?
C5 C6 C1 120.78(15) . . ?
C5 C6 H7 119.6 . . ?
C1 C6 H7 119.6 . . ?
N1 C7 C8 107.06(13) . . ?
N1 C7 C1 123.60(14) . . ?
C8 C7 C1 129.28(14) . . ?
C7 C8 C9 107.95(14) . . ?
C7 C8 H8 126.0 . . ?
C9 C8 H8 126.0 . . ?
C10 C9 C8 107.55(14) . . ?
C10 C9 H9 126.2 . . ?
C8 C9 H9 126.2 . . ?
N1 C10 C9 107.33(13) . . ?
N1 C10 C11 121.87(14) . . ?
C9 C10 C11 130.80(14) . . ?
N2 C11 C12 121.60(14) . . ?
N2 C11 C10 116.76(14) . . ?
C12 C11 C10 121.63(15) . . ?
C13 C12 C11 117.89(15) . . ?
C13 C12 H10 121.1 . . ?
C11 C12 H10 121.1 . . ?
N3 C13 C12 121.32(14) . . ?
N3 C13 C15 116.35(13) . . ?
C12 C13 C15 122.33(15) . . ?
N2 C14 N3 130.35(14) . . ?
N2 C14 Br1 115.65(11) . . ?
N3 C14 Br1 113.97(11) . . ?
N4 C15 C16 107.57(13) . . ?
N4 C15 C13 121.15(14) . . ?
C16 C15 C13 131.28(14) . . ?
C15 C16 C17 107.54(14) . . ?
C15 C16 H11 126.2 . . ?
C17 C16 H11 126.2 . . ?
C18 C17 C16 107.96(14) . . ?
C18 C17 H12 126.0 . . ?
C16 C17 H12 126.0 . . ?
N4 C18 C17 107.15(12) . . ?
N4 C18 C19 123.07(14) . . ?
C17 C18 C19 129.65(14) . . ?
C20 C19 C24 118.28(14) . . ?
C20 C19 C18 122.42(14) . . ?
C24 C19 C18 119.23(14) . . ?
C21 C20 C19 120.76(14) . . ?
C21 C20 H13 119.6 . . ?
C19 C20 H13 119.6 . . ?
C22 C21 C20 120.35(15) . . ?
C22 C21 H14 119.8 . . ?
C20 C21 H14 119.8 . . ?
C21 C22 C23 119.41(14) . . ?
C21 C22 H15 120.3 . . ?
C23 C22 H15 120.3 . . ?
C24 C23 C22 120.39(14) . . ?
C24 C23 H16 119.8 . . ?
C22 C23 H16 119.8 . . ?
C23 C24 C19 120.78(15) . . ?
C23 C24 H17 119.6 . . ?
C19 C24 H17 119.6 . . ?

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
C6 C1 C2 C3 -1.0(2) . . . . ?
C7 C1 C2 C3 177.45(15) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C7 C1 C6 C5 -177.65(14) . . . . ?
C10 N1 C7 C8 -0.09(16) . . . . ?
C10 N1 C7 C1 177.51(13) . . . . ?
C6 C1 C7 N1 3.9(2) . . . . ?
C2 C1 C7 N1 -174.49(14) . . . . ?
C6 C1 C7 C8 -179.05(15) . . . . ?
C2 C1 C7 C8 2.5(2) . . . . ?
N1 C7 C8 C9 -0.14(17) . . . . ?
C1 C7 C8 C9 -177.56(15) . . . . ?
C7 C8 C9 C10 0.32(17) . . . . ?
C7 N1 C10 C9 0.29(16) . . . . ?
C7 N1 C10 C11 179.26(13) . . . . ?
C8 C9 C10 N1 -0.37(17) . . . . ?
C8 C9 C10 C11 -179.22(15) . . . . ?
C14 N2 C11 C12 1.3(2) . . . . ?
C14 N2 C11 C10 -177.64(13) . . . . ?
N1 C10 C11 N2 -8.9(2) . . . . ?
C9 C10 C11 N2 169.79(15) . . . . ?
N1 C10 C11 C12 172.17(14) . . . . ?
C9 C10 C11 C12 -9.1(3) . . . . ?
N2 C11 C12 C13 -1.7(2) . . . . ?
C10 C11 C12 C13 177.19(14) . . . . ?
C14 N3 C13 C12 -1.1(2) . . . . ?
C14 N3 C13 C15 178.39(13) . . . . ?
C11 C12 C13 N3 1.6(2) . . . . ?
C11 C12 C13 C15 -177.91(14) . . . . ?
C11 N2 C14 N3 -0.9(2) . . . . ?
C11 N2 C14 Br1 176.83(10) . . . . ?
C13 N3 C14 N2 0.8(2) . . . . ?
C13 N3 C14 Br1 -176.93(10) . . . . ?
C18 N4 C15 C16 -1.44(16) . . . . ?
C18 N4 C15 C13 178.26(13) . . . . ?
N3 C13 C15 N4 10.4(2) . . . . ?
C12 C13 C15 N4 -170.05(14) . . . . ?
N3 C13 C15 C16 -169.97(15) . . . . ?
C12 C13 C15 C16 9.6(3) . . . . ?
N4 C15 C16 C17 0.94(16) . . . . ?
C13 C15 C16 C17 -178.71(15) . . . . ?
C15 C16 C17 C18 -0.13(16) . . . . ?
C15 N4 C18 C17 1.35(16) . . . . ?
C15 N4 C18 C19 -174.82(13) . . . . ?
C16 C17 C18 N4 -0.74(16) . . . . ?
C16 C17 C18 C19 175.09(14) . . . . ?
N4 C18 C19 C20 -5.3(2) . . . . ?
C17 C18 C19 C20 179.42(14) . . . . ?
N4 C18 C19 C24 171.55(13) . . . . ?
C17 C18 C19 C24 -3.7(2) . . . . ?
C24 C19 C20 C21 -1.4(2) . . . . ?
C18 C19 C20 C21 175.52(13) . . . . ?
C19 C20 C21 C22 0.0(2) . . . . ?
C20 C21 C22 C23 1.3(2) . . . . ?
C21 C22 C23 C24 -1.3(2) . . . . ?
C22 C23 C24 C19 -0.1(2) . . . . ?
C20 C19 C24 C23 1.4(2) . . . . ?
C18 C19 C24 C23 -175.59(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        65.99
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_31212m
_database_code_depnum_ccdc_archive 'CCDC 1485808'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Br N4, C16 H36 N, Cl, O'
_chemical_formula_sum            'C28 H45 Br Cl N5 O'
_chemical_formula_weight         583.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n '
_symmetry_Int_Tables_number      33

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'

_cell_length_a                   18.4725(3)
_cell_length_b                   8.38730(10)
_cell_length_c                   19.5557(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3029.85(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    18372
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      68.3

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    2.872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5456
_exptl_absorpt_correction_T_max  0.7621
_exptl_absorpt_process_details   
;Higashi, T. (1995). 
 Program for Absorption Correction.
 Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30843
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.52
_diffrn_reflns_theta_max         68.22
_reflns_number_total             5487
_reflns_number_gt                4946
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0600P)²+1.9434P] 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   -0.007(17)
_refine_ls_number_reflns         5487
_refine_ls_number_parameters     325
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.14445(16) 0.2424(4) -0.28472(16) 0.0265(7) Uani 1 1 d . . .
H1 H 0.0969 0.2374 -0.2851 0.032 Uiso 1 1 calc R . .
N2 N 0.20165(17) 0.4151(4) -0.12136(16) 0.0264(7) Uani 1 1 d . . .
N3 N 0.10183(16) 0.4647(4) -0.04482(16) 0.0260(7) Uani 1 1 d . . .
N4 N -0.0783(2) 0.3382(5) -0.1116(2) 0.0448(9) Uani 1 1 d . . .
H2 H -0.0768 0.2999 -0.1535 0.054 Uiso 1 1 calc R . .
N5 N -0.12876(16) -0.2472(4) -0.23700(15) 0.0216(6) Uani 1 1 d . . .
C1 C 0.1891(2) 0.1946(5) -0.3369(2) 0.0312(9) Uani 1 1 d . . .
H3 H 0.1741 0.1512 -0.3795 0.037 Uiso 1 1 calc R . .
C2 C 0.2595(2) 0.2207(5) -0.3168(2) 0.0302(9) Uani 1 1 d . . .
H4 H 0.3018 0.1978 -0.3427 0.036 Uiso 1 1 calc R . .
C3 C 0.2575(2) 0.2868(5) -0.2513(2) 0.0267(8) Uani 1 1 d . . .
H5 H 0.2984 0.3176 -0.2249 0.032 Uiso 1 1 calc R . .
C4 C 0.1864(2) 0.2997(4) -0.23140(18) 0.0253(8) Uani 1 1 d . . .
C5 C 0.1543(2) 0.3533(4) -0.16745(18) 0.0239(8) Uani 1 1 d . . .
C6 C 0.08118(19) 0.3444(4) -0.15397(18) 0.0237(8) Uani 1 1 d . . .
H6 H 0.0486 0.3016 -0.1868 0.028 Uiso 1 1 calc R . .
C7 C 0.05598(19) 0.3998(5) -0.0909(2) 0.0257(8) Uani 1 1 d . . .
C8 C 0.1711(2) 0.4653(4) -0.06464(18) 0.0248(8) Uani 1 1 d . . .
C9 C -0.02033(19) 0.3929(4) -0.07353(19) 0.0246(8) Uani 1 1 d . . .
C10 C -0.04623(17) 0.4432(4) -0.01076(17) 0.0184(7) Uani 1 1 d . . .
H7 H -0.0177 0.4856 0.0254 0.022 Uiso 1 1 calc R . .
C11 C -0.1186(2) 0.4223(5) -0.0093(2) 0.0340(10) Uani 1 1 d . . .
H8 H -0.1495 0.4491 0.0278 0.041 Uiso 1 1 calc R . .
C12 C -0.1407(2) 0.3558(5) -0.0702(2) 0.0326(9) Uani 1 1 d . . .
H9 H -0.1889 0.3271 -0.0822 0.039 Uiso 1 1 calc R . .
C13 C -0.15618(19) -0.1507(4) -0.29805(18) 0.0239(7) Uani 1 1 d . . .
H10 H -0.1997 -0.0908 -0.2835 0.029 Uiso 1 1 calc R . .
H11 H -0.1186 -0.0716 -0.3105 0.029 Uiso 1 1 calc R . .
C14 C -0.1752(2) -0.2461(5) -0.36159(19) 0.0271(8) Uani 1 1 d . . .
H12 H -0.2170 -0.3164 -0.3520 0.033 Uiso 1 1 calc R . .
H13 H -0.1336 -0.3138 -0.3750 0.033 Uiso 1 1 calc R . .
C15 C -0.1940(2) -0.1302(5) -0.42000(19) 0.0309(9) Uani 1 1 d . . .
H14 H -0.2203 -0.1892 -0.4561 0.037 Uiso 1 1 calc R . .
H15 H -0.2268 -0.0466 -0.4022 0.037 Uiso 1 1 calc R . .
C16 C -0.1281(3) -0.0512(6) -0.4514(2) 0.0472(12) Uani 1 1 d . . .
H16 H -0.1435 0.0214 -0.4879 0.071 Uiso 1 1 calc R . .
H17 H -0.0961 -0.1330 -0.4705 0.071 Uiso 1 1 calc R . .
H18 H -0.1021 0.0090 -0.4162 0.071 Uiso 1 1 calc R . .
C17 C -0.06294(19) -0.3460(4) -0.25749(19) 0.0242(8) Uani 1 1 d . . .
H19 H -0.0433 -0.3981 -0.2160 0.029 Uiso 1 1 calc R . .
H20 H -0.0790 -0.4313 -0.2890 0.029 Uiso 1 1 calc R . .
C18 C -0.00218(19) -0.2526(4) -0.2918(2) 0.0287(8) Uani 1 1 d . . .
H21 H -0.0189 -0.2126 -0.3367 0.034 Uiso 1 1 calc R . .
H22 H 0.0109 -0.1597 -0.2632 0.034 Uiso 1 1 calc R . .
C19 C 0.06388(19) -0.3582(5) -0.3018(2) 0.0294(8) Uani 1 1 d . . .
H23 H 0.0505 -0.4520 -0.3298 0.035 Uiso 1 1 calc R . .
H24 H 0.0809 -0.3971 -0.2568 0.035 Uiso 1 1 calc R . .
C20 C 0.1249(2) -0.2670(6) -0.3371(2) 0.0389(10) Uani 1 1 d . . .
H25 H 0.1668 -0.3374 -0.3429 0.058 Uiso 1 1 calc R . .
H26 H 0.1387 -0.1751 -0.3090 0.058 Uiso 1 1 calc R . .
H27 H 0.1084 -0.2299 -0.3820 0.058 Uiso 1 1 calc R . .
C21 C -0.10993(18) -0.1282(4) -0.18151(17) 0.0219(7) Uani 1 1 d . . .
H28 H -0.1536 -0.0637 -0.1716 0.026 Uiso 1 1 calc R . .
H29 H -0.0725 -0.0549 -0.1996 0.026 Uiso 1 1 calc R . .
C22 C -0.0825(2) -0.1982(4) -0.11477(18) 0.0245(8) Uani 1 1 d . . .
H30 H -0.0368 -0.2566 -0.1229 0.029 Uiso 1 1 calc R . .
H31 H -0.1185 -0.2745 -0.0964 0.029 Uiso 1 1 calc R . .
C23 C -0.0698(2) -0.0643(4) -0.06298(19) 0.0265(8) Uani 1 1 d . . .
H32 H -0.0319 0.0083 -0.0807 0.032 Uiso 1 1 calc R . .
H33 H -0.1149 -0.0019 -0.0576 0.032 Uiso 1 1 calc R . .
C24 C -0.0465(2) -0.1283(5) 0.0064(2) 0.0371(9) Uani 1 1 d . . .
H34 H -0.0392 -0.0392 0.0380 0.056 Uiso 1 1 calc R . .
H35 H -0.0012 -0.1878 0.0014 0.056 Uiso 1 1 calc R . .
H36 H -0.0842 -0.1992 0.0243 0.056 Uiso 1 1 calc R . .
C25 C -0.18571(19) -0.3635(4) -0.21280(19) 0.0248(8) Uani 1 1 d . . .
H37 H -0.1635 -0.4345 -0.1783 0.030 Uiso 1 1 calc R . .
H38 H -0.2003 -0.4307 -0.2521 0.030 Uiso 1 1 calc R . .
C26 C -0.2534(2) -0.2905(5) -0.1820(2) 0.0260(8) Uani 1 1 d . . .
H39 H -0.2749 -0.2139 -0.2147 0.031 Uiso 1 1 calc R . .
H40 H -0.2407 -0.2316 -0.1398 0.031 Uiso 1 1 calc R . .
C27 C -0.3081(2) -0.4199(5) -0.1653(2) 0.0302(9) Uani 1 1 d . . .
H41 H -0.2860 -0.4967 -0.1330 0.036 Uiso 1 1 calc R . .
H42 H -0.3204 -0.4785 -0.2077 0.036 Uiso 1 1 calc R . .
C28 C -0.3775(2) -0.3535(5) -0.1339(2) 0.0332(9) Uani 1 1 d . . .
H43 H -0.4109 -0.4414 -0.1239 0.050 Uiso 1 1 calc R . .
H44 H -0.4004 -0.2795 -0.1661 0.050 Uiso 1 1 calc R . .
H45 H -0.3659 -0.2971 -0.0914 0.050 Uiso 1 1 calc R . .
Br1 Br 0.234686(18) 0.56145(5) 0.00086(2) 0.03404(12) Uani 1 1 d . . .
Cl1 Cl -0.02870(4) 0.19480(10) -0.29268(4) 0.02492(18) Uani 1 1 d . . .
O1 O 0.44856(16) 0.0551(3) -0.40700(14) 0.0334(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.372(5) . ?
N1 C4 1.385(5) . ?
N1 H1 0.8800 . ?
N2 C8 1.314(5) . ?
N2 C5 1.358(5) . ?
N3 C8 1.337(5) . ?
N3 C7 1.351(5) . ?
N4 C9 1.384(5) . ?
N4 C12 1.417(5) . ?
N4 H2 0.8800 . ?
N5 C25 1.510(4) . ?
N5 C21 1.515(5) . ?
N5 C17 1.525(4) . ?
N5 C13 1.529(4) . ?
C1 C2 1.376(6) . ?
C1 H3 0.9500 . ?
C2 C3 1.397(5) . ?
C2 H4 0.9500 . ?
C3 C4 1.375(5) . ?
C3 H5 0.9500 . ?
C4 C5 1.455(5) . ?
C5 C6 1.379(5) . ?
C6 C7 1.397(5) . ?
C6 H6 0.9500 . ?
C7 C9 1.451(5) . ?
C8 Br1 1.916(4) . ?
C9 C10 1.383(5) . ?
C10 C11 1.349(5) . ?
C10 H7 0.9500 . ?
C11 C12 1.376(6) . ?
C11 H8 0.9500 . ?
C12 H9 0.9500 . ?
C13 C14 1.519(5) . ?
C13 H10 0.9900 . ?
C13 H11 0.9900 . ?
C14 C15 1.539(5) . ?
C14 H12 0.9900 . ?
C14 H13 0.9900 . ?
C15 C16 1.516(6) . ?
C15 H14 0.9900 . ?
C15 H15 0.9900 . ?
C16 H16 0.9800 . ?
C16 H17 0.9800 . ?
C16 H18 0.9800 . ?
C17 C18 1.525(5) . ?
C17 H19 0.9900 . ?
C17 H20 0.9900 . ?
C18 C19 1.520(5) . ?
C18 H21 0.9900 . ?
C18 H22 0.9900 . ?
C19 C20 1.528(6) . ?
C19 H23 0.9900 . ?
C19 H24 0.9900 . ?
C20 H25 0.9800 . ?
C20 H26 0.9800 . ?
C20 H27 0.9800 . ?
C21 C22 1.518(5) . ?
C21 H28 0.9900 . ?
C21 H29 0.9900 . ?
C22 C23 1.531(5) . ?
C22 H30 0.9900 . ?
C22 H31 0.9900 . ?
C23 C24 1.520(6) . ?
C23 H32 0.9900 . ?
C23 H33 0.9900 . ?
C24 H34 0.9800 . ?
C24 H35 0.9800 . ?
C24 H36 0.9800 . ?
C25 C26 1.517(5) . ?
C25 H37 0.9900 . ?
C25 H38 0.9900 . ?
C26 C27 1.519(5) . ?
C26 H39 0.9900 . ?
C26 H40 0.9900 . ?
C27 C28 1.527(5) . ?
C27 H41 0.9900 . ?
C27 H42 0.9900 . ?
C28 H43 0.9800 . ?
C28 H44 0.9800 . ?
C28 H45 0.9800 . ?

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
C1 N1 C4 109.0(3) . . ?
C1 N1 H1 125.5 . . ?
C4 N1 H1 125.5 . . ?
C8 N2 C5 113.9(3) . . ?
C8 N3 C7 114.1(3) . . ?
C9 N4 C12 106.7(4) . . ?
C9 N4 H2 126.6 . . ?
C12 N4 H2 126.6 . . ?
C25 N5 C21 111.1(3) . . ?
C25 N5 C17 106.7(3) . . ?
C21 N5 C17 111.3(3) . . ?
C25 N5 C13 110.8(3) . . ?
C21 N5 C13 106.7(3) . . ?
C17 N5 C13 110.3(3) . . ?
N1 C1 C2 108.0(3) . . ?
N1 C1 H3 126.0 . . ?
C2 C1 H3 126.0 . . ?
C1 C2 C3 107.5(4) . . ?
C1 C2 H4 126.3 . . ?
C3 C2 H4 126.3 . . ?
C4 C3 C2 108.4(4) . . ?
C4 C3 H5 125.8 . . ?
C2 C3 H5 125.8 . . ?
C3 C4 N1 107.1(3) . . ?
C3 C4 C5 131.0(3) . . ?
N1 C4 C5 121.8(3) . . ?
N2 C5 C6 121.6(3) . . ?
N2 C5 C4 115.2(3) . . ?
C6 C5 C4 123.1(3) . . ?
C5 C6 C7 118.5(3) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
N3 C7 C6 120.9(3) . . ?
N3 C7 C9 117.9(3) . . ?
C6 C7 C9 121.2(3) . . ?
N2 C8 N3 130.9(3) . . ?
N2 C8 Br1 115.8(3) . . ?
N3 C8 Br1 113.2(3) . . ?
C10 C9 N4 108.1(3) . . ?
C10 C9 C7 122.1(3) . . ?
N4 C9 C7 129.7(4) . . ?
C11 C10 C9 108.7(4) . . ?
C11 C10 H7 125.6 . . ?
C9 C10 H7 125.6 . . ?
C10 C11 C12 109.2(4) . . ?
C10 C11 H8 125.4 . . ?
C12 C11 H8 125.4 . . ?
C11 C12 N4 107.2(3) . . ?
C11 C12 H9 126.4 . . ?
N4 C12 H9 126.4 . . ?
C14 C13 N5 115.9(3) . . ?
C14 C13 H10 108.3 . . ?
N5 C13 H10 108.3 . . ?
C14 C13 H11 108.3 . . ?
N5 C13 H11 108.3 . . ?
H10 C13 H11 107.4 . . ?
C13 C14 C15 109.1(3) . . ?
C13 C14 H12 109.9 . . ?
C15 C14 H12 109.9 . . ?
C13 C14 H13 109.9 . . ?
C15 C14 H13 109.9 . . ?
H12 C14 H13 108.3 . . ?
C16 C15 C14 113.3(3) . . ?
C16 C15 H14 108.9 . . ?
C14 C15 H14 108.9 . . ?
C16 C15 H15 108.9 . . ?
C14 C15 H15 108.9 . . ?
H14 C15 H15 107.7 . . ?
C15 C16 H16 109.5 . . ?
C15 C16 H17 109.5 . . ?
H16 C16 H17 109.5 . . ?
C15 C16 H18 109.5 . . ?
H16 C16 H18 109.5 . . ?
H17 C16 H18 109.5 . . ?
C18 C17 N5 115.1(3) . . ?
C18 C17 H19 108.5 . . ?
N5 C17 H19 108.5 . . ?
C18 C17 H20 108.5 . . ?
N5 C17 H20 108.5 . . ?
H19 C17 H20 107.5 . . ?
C19 C18 C17 110.4(3) . . ?
C19 C18 H21 109.6 . . ?
C17 C18 H21 109.6 . . ?
C19 C18 H22 109.6 . . ?
C17 C18 H22 109.6 . . ?
H21 C18 H22 108.1 . . ?
C18 C19 C20 111.0(3) . . ?
C18 C19 H23 109.4 . . ?
C20 C19 H23 109.4 . . ?
C18 C19 H24 109.4 . . ?
C20 C19 H24 109.4 . . ?
H23 C19 H24 108.0 . . ?
C19 C20 H25 109.5 . . ?
C19 C20 H26 109.5 . . ?
H25 C20 H26 109.5 . . ?
C19 C20 H27 109.5 . . ?
H25 C20 H27 109.5 . . ?
H26 C20 H27 109.5 . . ?
N5 C21 C22 115.9(3) . . ?
N5 C21 H28 108.3 . . ?
C22 C21 H28 108.3 . . ?
N5 C21 H29 108.3 . . ?
C22 C21 H29 108.3 . . ?
H28 C21 H29 107.4 . . ?
C21 C22 C23 109.6(3) . . ?
C21 C22 H30 109.7 . . ?
C23 C22 H30 109.7 . . ?
C21 C22 H31 109.7 . . ?
C23 C22 H31 109.7 . . ?
H30 C22 H31 108.2 . . ?
C24 C23 C22 112.0(3) . . ?
C24 C23 H32 109.2 . . ?
C22 C23 H32 109.2 . . ?
C24 C23 H33 109.2 . . ?
C22 C23 H33 109.2 . . ?
H32 C23 H33 107.9 . . ?
C23 C24 H34 109.5 . . ?
C23 C24 H35 109.5 . . ?
H34 C24 H35 109.5 . . ?
C23 C24 H36 109.5 . . ?
H34 C24 H36 109.5 . . ?
H35 C24 H36 109.5 . . ?
N5 C25 C26 116.0(3) . . ?
N5 C25 H37 108.3 . . ?
C26 C25 H37 108.3 . . ?
N5 C25 H38 108.3 . . ?
C26 C25 H38 108.3 . . ?
H37 C25 H38 107.4 . . ?
C25 C26 C27 110.2(3) . . ?
C25 C26 H39 109.6 . . ?
C27 C26 H39 109.6 . . ?
C25 C26 H40 109.6 . . ?
C27 C26 H40 109.6 . . ?
H39 C26 H40 108.1 . . ?
C26 C27 C28 112.6(3) . . ?
C26 C27 H41 109.1 . . ?
C28 C27 H41 109.1 . . ?
C26 C27 H42 109.1 . . ?
C28 C27 H42 109.1 . . ?
H41 C27 H42 107.8 . . ?
C27 C28 H43 109.5 . . ?
C27 C28 H44 109.5 . . ?
H43 C28 H44 109.5 . . ?
C27 C28 H45 109.5 . . ?
H43 C28 H45 109.5 . . ?
H44 C28 H45 109.5 . . ?

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
C4 N1 C1 C2 0.3(4) . . . . ?
N1 C1 C2 C3 -0.5(5) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C2 C3 C4 N1 -0.3(4) . . . . ?
C2 C3 C4 C5 176.8(4) . . . . ?
C1 N1 C4 C3 0.0(4) . . . . ?
C1 N1 C4 C5 -177.5(3) . . . . ?
C8 N2 C5 C6 -0.6(5) . . . . ?
C8 N2 C5 C4 178.8(3) . . . . ?
C3 C4 C5 N2 6.9(6) . . . . ?
N1 C4 C5 N2 -176.3(3) . . . . ?
C3 C4 C5 C6 -173.7(4) . . . . ?
N1 C4 C5 C6 3.1(6) . . . . ?
N2 C5 C6 C7 -0.4(5) . . . . ?
C4 C5 C6 C7 -179.8(3) . . . . ?
C8 N3 C7 C6 -1.9(5) . . . . ?
C8 N3 C7 C9 179.5(3) . . . . ?
C5 C6 C7 N3 1.8(5) . . . . ?
C5 C6 C7 C9 -179.7(4) . . . . ?
C5 N2 C8 N3 0.5(6) . . . . ?
C5 N2 C8 Br1 -177.6(2) . . . . ?
C7 N3 C8 N2 0.8(6) . . . . ?
C7 N3 C8 Br1 178.9(3) . . . . ?
C12 N4 C9 C10 -0.2(4) . . . . ?
C12 N4 C9 C7 179.0(4) . . . . ?
N3 C7 C9 C10 -3.1(5) . . . . ?
C6 C7 C9 C10 178.3(3) . . . . ?
N3 C7 C9 N4 177.7(4) . . . . ?
C6 C7 C9 N4 -0.9(6) . . . . ?
N4 C9 C10 C11 -0.5(4) . . . . ?
C7 C9 C10 C11 -179.8(4) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C10 C11 C12 N4 -1.2(5) . . . . ?
C9 N4 C12 C11 0.9(4) . . . . ?
C25 N5 C13 C14 -61.6(4) . . . . ?
C21 N5 C13 C14 177.3(3) . . . . ?
C17 N5 C13 C14 56.3(4) . . . . ?
N5 C13 C14 C15 -174.1(3) . . . . ?
C13 C14 C15 C16 75.8(4) . . . . ?
C25 N5 C17 C18 172.8(3) . . . . ?
C21 N5 C17 C18 -65.8(4) . . . . ?
C13 N5 C17 C18 52.3(4) . . . . ?
N5 C17 C18 C19 172.9(3) . . . . ?
C17 C18 C19 C20 179.2(3) . . . . ?
C25 N5 C21 C22 58.0(4) . . . . ?
C17 N5 C21 C22 -60.8(4) . . . . ?
C13 N5 C21 C22 178.9(3) . . . . ?
N5 C21 C22 C23 -177.0(3) . . . . ?
C21 C22 C23 C24 176.6(3) . . . . ?
C21 N5 C25 C26 51.8(4) . . . . ?
C17 N5 C25 C26 173.2(3) . . . . ?
C13 N5 C25 C26 -66.7(4) . . . . ?
N5 C25 C26 C27 175.4(3) . . . . ?
C25 C26 C27 C28 179.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Cl1 0.88 2.35 3.227(3) 173.2 .
N4 H2 Cl1 0.88 3.00 3.850(4) 164.2 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        68.22
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.066
####################################################################### 
# 
# 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_40306m
_database_code_depnum_ccdc_archive 'CCDC 1485809'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' 2(C28 H30 N3), 2(C12 H9 Br N4), 2(Cl), O'
_chemical_formula_sum            'C80 H78 Br2 Cl2 N14 O'
_chemical_formula_weight         1482.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_Int_Tables_number      1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   11.2758(2)
_cell_length_b                   13.2794(2)
_cell_length_c                   14.0394(3)
_cell_angle_alpha                65.8676(7)
_cell_angle_beta                 83.1022(9)
_cell_angle_gamma                65.9622(7)
_cell_volume                     1749.38(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    2.632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5157
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16737
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_sigmaI/netI    0.1094
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         65.00
_reflns_number_total             8979
_reflns_number_gt                6079
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1003P)²+0.1174P] 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   0.00(3)
_refine_ls_number_reflns         8979
_refine_ls_number_parameters     892
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0716
_refine_ls_wR_factor_ref         0.2119
_refine_ls_wR_factor_gt          0.1647
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.008
_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 0.8003(10) 0.4558(8) 0.9259(7) 0.055(3) Uani 1 1 d . . .
H1 H 0.7318 0.4395 0.9272 0.066 Uiso 1 1 calc R . .
N2 N 1.0906(10) 0.2110(8) 0.8978(7) 0.051(2) Uani 1 1 d . . .
N3 N 1.0422(9) 0.0651(7) 0.8704(6) 0.043(2) Uani 1 1 d . . .
N4 N 0.7111(10) 0.0841(7) 0.9214(7) 0.050(2) Uani 1 1 d . . .
H2 H 0.6778 0.1282 0.9583 0.060 Uiso 1 1 calc R . .
N5 N 0.7402(9) 0.7854(7) 0.2415(6) 0.046(2) Uani 1 1 d . . .
H3 H 0.7017 0.8461 0.2606 0.056 Uiso 1 1 calc R . .
N6 N 0.7653(9) 0.5027(7) 0.4656(6) 0.043(2) Uani 1 1 d . . .
N7 N 0.6790(9) 0.5326(8) 0.6204(6) 0.046(2) Uani 1 1 d . . .
C81 C 0.5523(12) 0.8509(10) 0.5974(10) 0.050(3) Uani 1 1 d . . .
H79 H 0.5650 0.9057 0.5319 0.060 Uiso 1 1 calc R . .
N9 N 1.5662(9) 0.3987(7) 0.2898(6) 0.044(2) Uani 1 1 d . . .
N10 N 1.4231(11) 0.4283(7) 0.6190(7) 0.062(3) Uani 1 1 d . . .
N11 N 1.3905(9) 0.7846(7) 0.3169(7) 0.045(2) Uani 1 1 d . . .
N12 N 1.2024(9) 0.3270(7) 0.4575(6) 0.046(2) Uani 1 1 d . . .
N13 N 0.9694(9) 0.7360(7) 0.4278(6) 0.041(2) Uani 1 1 d . . .
N14 N 1.1910(9) 0.6593(7) 0.1315(6) 0.041(2) Uani 1 1 d . . .
Br1 Br 1.29820(12) 0.03306(10) 0.86152(9) 0.0602(4) Uani 1 1 d . . .
Br2 Br 0.78180(11) 0.30157(8) 0.63368(8) 0.0545(4) Uani 1 1 d . . .
Cl1 Cl 0.5190(3) 0.4669(2) 0.9349(2) 0.0511(8) Uani 1 1 d . . .
Cl2 Cl 0.5983(3) 1.0256(2) 0.29851(19) 0.0475(7) Uani 1 1 d . . .
C1 C 0.7964(16) 0.5604(12) 0.9275(10) 0.064(4) Uani 1 1 d . . .
H5 H 0.7215 0.6260 0.9313 0.076 Uiso 1 1 calc R . .
C2 C 0.9220(15) 0.5502(12) 0.9224(11) 0.072(4) Uani 1 1 d . . .
H6 H 0.9485 0.6100 0.9214 0.087 Uiso 1 1 calc R . .
C3 C 1.0064(14) 0.4409(11) 0.9191(10) 0.062(4) Uani 1 1 d . . .
H7 H 1.0982 0.4131 0.9155 0.075 Uiso 1 1 calc R . .
C4 C 0.9286(13) 0.3797(10) 0.9219(8) 0.048(3) Uani 1 1 d . . .
C5 C 0.9612(13) 0.2696(10) 0.9075(9) 0.045(3) Uani 1 1 d . . .
C6 C 0.8737(13) 0.2224(9) 0.9057(8) 0.051(3) Uani 1 1 d . . .
H8 H 0.7853 0.2603 0.9187 0.061 Uiso 1 1 calc R . .
C7 C 0.9126(11) 0.1210(8) 0.8855(7) 0.038(2) Uani 1 1 d . . .
C8 C 1.1193(12) 0.1168(9) 0.8792(8) 0.049(3) Uani 1 1 d . . .
C9 C 0.8300(12) 0.0666(9) 0.8768(8) 0.046(3) Uani 1 1 d . . .
C10 C 0.8480(12) -0.0079(9) 0.8273(8) 0.047(3) Uani 1 1 d . . .
H9 H 0.9233 -0.0386 0.7928 0.056 Uiso 1 1 calc R . .
C11 C 0.7339(14) -0.0310(11) 0.8365(9) 0.061(3) Uani 1 1 d . . .
H10 H 0.7171 -0.0751 0.8048 0.073 Uiso 1 1 calc R . .
C12 C 0.6512(14) 0.0215(10) 0.8993(9) 0.059(3) Uani 1 1 d . . .
H11 H 0.5705 0.0162 0.9226 0.070 Uiso 1 1 calc R . .
C13 C 0.7847(12) 0.7928(11) 0.1462(8) 0.051(3) Uani 1 1 d . . .
H12 H 0.7790 0.8647 0.0885 0.061 Uiso 1 1 calc R . .
C14 C 0.8399(12) 0.6792(10) 0.1460(8) 0.052(3) Uani 1 1 d . . .
H13 H 0.8789 0.6597 0.0886 0.063 Uiso 1 1 calc R . .
C15 C 0.8286(13) 0.5972(11) 0.2451(8) 0.055(3) Uani 1 1 d . . .
H14 H 0.8575 0.5127 0.2679 0.065 Uiso 1 1 calc R . .
C16 C 0.7649(11) 0.6675(9) 0.3034(8) 0.044(3) Uani 1 1 d . . .
C17 C 0.7317(11) 0.6252(9) 0.4131(9) 0.046(3) Uani 1 1 d . . .
C18 C 0.6706(11) 0.7012(9) 0.4632(7) 0.040(3) Uani 1 1 d . . .
H15 H 0.6444 0.7855 0.4261 0.048 Uiso 1 1 calc R . .
C19 C 0.6471(11) 0.6536(9) 0.5697(8) 0.041(2) Uani 1 1 d . . .
C20 C 0.7365(12) 0.4708(10) 0.5627(9) 0.048(3) Uani 1 1 d . . .
C21 C 0.5867(10) 0.7276(9) 0.6282(8) 0.040(2) Uani 1 1 d . . .
N15 N 0.5546(10) 0.6797(8) 0.7293(7) 0.046(2) Uani 1 1 d . . .
H80 H 0.5686 0.6036 0.7661 0.055 Uiso 1 1 calc R . .
C23 C 0.4975(11) 0.7701(9) 0.7626(8) 0.049(3) Uani 1 1 d . . .
H17 H 0.4645 0.7616 0.8297 0.059 Uiso 1 1 calc R . .
C24 C 0.4945(12) 0.8766(10) 0.6845(9) 0.052(3) Uani 1 1 d . . .
H18 H 0.4600 0.9530 0.6884 0.063 Uiso 1 1 calc R . .
C25 C 1.5781(12) 0.2170(9) 0.4405(8) 0.051(3) Uani 1 1 d . . .
H19 H 1.6168 0.1680 0.4021 0.061 Uiso 1 1 calc R . .
C26 C 1.5525(12) 0.1675(10) 0.5471(9) 0.051(3) Uani 1 1 d . . .
H20 H 1.5741 0.0834 0.5795 0.061 Uiso 1 1 calc R . .
C27 C 1.4972(13) 0.2353(11) 0.6074(10) 0.059(3) Uani 1 1 d . . .
H21 H 1.4794 0.1982 0.6782 0.071 Uiso 1 1 calc R . .
C28 C 1.4684(13) 0.3595(10) 0.5614(9) 0.055(3) Uani 1 1 d . . .
C29 C 1.4872(11) 0.4132(9) 0.4538(7) 0.040(2) Uani 1 1 d . . .
C30 C 1.5439(11) 0.3413(9) 0.3941(8) 0.042(3) Uani 1 1 d . . .
C31 C 1.3994(11) 0.6073(9) 0.4677(8) 0.040(2) Uani 1 1 d . . .
C32 C 1.3809(11) 0.5513(9) 0.5751(9) 0.047(3) Uani 1 1 d . . .
C33 C 1.3273(12) 0.6213(10) 0.6352(9) 0.052(3) Uani 1 1 d . . .
H22 H 1.3147 0.5852 0.7075 0.062 Uiso 1 1 calc R . .
C34 C 1.2933(12) 0.7452(11) 0.5852(10) 0.051(3) Uani 1 1 d . . .
H23 H 1.2572 0.7933 0.6245 0.061 Uiso 1 1 calc R . .
C35 C 1.3109(12) 0.8007(9) 0.4786(9) 0.052(3) Uani 1 1 d . . .
H24 H 1.2848 0.8854 0.4467 0.062 Uiso 1 1 calc R . .
C36 C 1.3655(11) 0.7335(10) 0.4202(8) 0.047(3) Uani 1 1 d . . .
C37 C 1.5504(12) 0.5791(9) 0.1356(8) 0.048(3) Uani 1 1 d . . .
H25 H 1.5897 0.5338 0.0942 0.057 Uiso 1 1 calc R . .
C38 C 1.5315(11) 0.5230(9) 0.2399(8) 0.045(3) Uani 1 1 d . . .
C39 C 1.4745(11) 0.5913(9) 0.3022(8) 0.044(3) Uani 1 1 d . . .
C40 C 1.4396(11) 0.7192(9) 0.2550(8) 0.043(3) Uani 1 1 d . . .
C41 C 1.4589(12) 0.7725(10) 0.1472(8) 0.052(3) Uani 1 1 d . . .
H26 H 1.4354 0.8568 0.1134 0.062 Uiso 1 1 calc R . .
C42 C 1.5115(12) 0.7013(9) 0.0930(8) 0.049(3) Uani 1 1 d . . .
H27 H 1.5219 0.7390 0.0205 0.059 Uiso 1 1 calc R . .
C43 C 1.4539(12) 0.5375(9) 0.4072(8) 0.044(3) Uani 1 1 d . . .
C44 C 1.6317(11) 0.3255(9) 0.2273(8) 0.045(3) Uani 1 1 d . . .
H28 H 1.5875 0.3677 0.1567 0.054 Uiso 1 1 calc R . .
H29 H 1.6224 0.2476 0.2610 0.054 Uiso 1 1 calc R . .
C45 C 1.7744(13) 0.3021(11) 0.2166(9) 0.059(3) Uani 1 1 d . . .
H30 H 1.8088 0.2617 0.1676 0.071 Uiso 1 1 calc R . .
H31 H 1.7829 0.3803 0.1849 0.071 Uiso 1 1 calc R . .
C46 C 1.8572(14) 0.2268(13) 0.3170(10) 0.074(4) Uani 1 1 d . . .
H32 H 1.9475 0.2175 0.3027 0.112 Uiso 1 1 calc R . .
H33 H 1.8530 0.1476 0.3476 0.112 Uiso 1 1 calc R . .
H34 H 1.8251 0.2664 0.3660 0.112 Uiso 1 1 calc R . .
C47 C 1.4491(16) 0.3604(13) 0.7476(13) 0.089(5) Uani 1 1 d . . .
H35 H 1.5240 0.2818 0.7686 0.107 Uiso 1 1 calc R . .
H36 H 1.4637 0.4109 0.7770 0.107 Uiso 1 1 calc R . .
C48 C 1.3322(15) 0.3468(13) 0.7777(15) 0.103(6) Uani 1 1 d . . .
H37 H 1.3192 0.2930 0.7515 0.123 Uiso 1 1 calc R . .
H38 H 1.2566 0.4250 0.7544 0.123 Uiso 1 1 calc R . .
C49 C 1.3607(15) 0.2834(11) 0.9094(9) 0.069(4) Uani 1 1 d . . .
H39 H 1.2853 0.2675 0.9432 0.103 Uiso 1 1 calc R . .
H40 H 1.3754 0.3384 0.9319 0.103 Uiso 1 1 calc R . .
H41 H 1.4377 0.2078 0.9290 0.103 Uiso 1 1 calc R . .
C50 C 1.3703(13) 0.9153(9) 0.2692(9) 0.054(3) Uani 1 1 d . . .
H42 H 1.4347 0.9274 0.2158 0.064 Uiso 1 1 calc R . .
H43 H 1.3839 0.9389 0.3241 0.064 Uiso 1 1 calc R . .
C51 C 1.2335(13) 0.9935(9) 0.2190(9) 0.051(3) Uani 1 1 d . . .
H44 H 1.2202 0.9707 0.1635 0.061 Uiso 1 1 calc R . .
H45 H 1.1691 0.9808 0.2721 0.061 Uiso 1 1 calc R . .
C52 C 1.2136(16) 1.1245(10) 0.1725(10) 0.074(5) Uani 1 1 d . . .
H46 H 1.1244 1.1744 0.1422 0.110 Uiso 1 1 calc R . .
H47 H 1.2750 1.1374 0.1178 0.110 Uiso 1 1 calc R . .
H48 H 1.2285 1.1464 0.2274 0.110 Uiso 1 1 calc R . .
C53 C 1.3302(12) 0.3340(9) 0.2009(8) 0.046(3) Uani 1 1 d . . .
H49 H 1.3759 0.2785 0.1696 0.055 Uiso 1 1 calc R . .
C54 C 1.3010(12) 0.2896(10) 0.3039(9) 0.052(3) Uani 1 1 d . . .
H50 H 1.3262 0.2055 0.3418 0.062 Uiso 1 1 calc R . .
C55 C 1.2357(11) 0.3666(9) 0.3517(8) 0.040(2) Uani 1 1 d . . .
C56 C 1.1958(11) 0.4916(9) 0.2942(8) 0.043(3) Uani 1 1 d . . .
C57 C 1.2297(11) 0.5344(8) 0.1885(8) 0.043(3) Uani 1 1 d . . .
C58 C 1.2964(12) 0.4547(9) 0.1408(8) 0.049(3) Uani 1 1 d . . .
H51 H 1.3177 0.4825 0.0698 0.059 Uiso 1 1 calc R . .
C59 C 1.1318(12) 0.4056(9) 0.5034(7) 0.045(3) Uani 1 1 d . . .
C60 C 1.0916(12) 0.3678(10) 0.6048(8) 0.052(3) Uani 1 1 d . . .
H52 H 1.1117 0.2846 0.6442 0.062 Uiso 1 1 calc R . .
C61 C 1.0236(12) 0.4481(10) 0.6491(8) 0.050(3) Uani 1 1 d . . .
H53 H 1.0015 0.4189 0.7198 0.060 Uiso 1 1 calc R . .
C62 C 0.9861(12) 0.5703(11) 0.5938(9) 0.052(3) Uani 1 1 d . . .
H54 H 0.9388 0.6246 0.6259 0.062 Uiso 1 1 calc R . .
C63 C 1.0192(11) 0.6134(9) 0.4890(7) 0.040(3) Uani 1 1 d . . .
C64 C 1.0921(12) 0.5308(9) 0.4453(8) 0.047(3) Uani 1 1 d . . .
C65 C 1.0821(11) 0.6987(9) 0.2812(8) 0.043(3) Uani 1 1 d . . .
C66 C 1.0063(11) 0.7808(9) 0.3229(8) 0.041(2) Uani 1 1 d . . .
C67 C 0.9569(12) 0.9037(9) 0.2629(8) 0.048(3) Uani 1 1 d . . .
H55 H 0.9041 0.9598 0.2918 0.058 Uiso 1 1 calc R . .
C68 C 0.9879(12) 0.9410(9) 0.1592(8) 0.046(3) Uani 1 1 d . . .
H56 H 0.9552 1.0249 0.1177 0.055 Uiso 1 1 calc R . .
C69 C 1.0636(12) 0.8641(9) 0.1120(8) 0.049(3) Uani 1 1 d . . .
H57 H 1.0806 0.8943 0.0401 0.059 Uiso 1 1 calc R . .
C70 C 1.1148(11) 0.7396(9) 0.1739(8) 0.040(3) Uani 1 1 d . . .
C71 C 1.1261(10) 0.5745(9) 0.3384(8) 0.037(2) Uani 1 1 d . . .
C72 C 1.2372(12) 0.1984(9) 0.5163(9) 0.053(3) Uani 1 1 d . . .
H58 H 1.2564 0.1769 0.5908 0.064 Uiso 1 1 calc R . .
H59 H 1.3164 0.1528 0.4889 0.064 Uiso 1 1 calc R . .
C73 C 1.1248(14) 0.1639(10) 0.5074(9) 0.062(4) Uani 1 1 d . . .
H60 H 1.0412 0.2260 0.5135 0.074 Uiso 1 1 calc R . .
H61 H 1.1231 0.1628 0.4375 0.074 Uiso 1 1 calc R . .
C74 C 1.1368(17) 0.0468(13) 0.5875(12) 0.084(5) Uani 1 1 d . . .
H62 H 1.0624 0.0302 0.5794 0.127 Uiso 1 1 calc R . .
H63 H 1.1387 0.0473 0.6569 0.127 Uiso 1 1 calc R . .
H64 H 1.2175 -0.0156 0.5797 0.127 Uiso 1 1 calc R . .
C75 C 0.8879(11) 0.8195(9) 0.4744(8) 0.046(3) Uani 1 1 d . . .
H65 H 0.8320 0.7836 0.5240 0.056 Uiso 1 1 calc R . .
H66 H 0.8303 0.8940 0.4185 0.056 Uiso 1 1 calc R . .
C76 C 0.9624(12) 0.8523(10) 0.5313(8) 0.051(3) Uani 1 1 d . . .
H67 H 1.0062 0.9016 0.4803 0.061 Uiso 1 1 calc R . .
H68 H 1.0301 0.7783 0.5799 0.061 Uiso 1 1 calc R . .
C77 C 0.8700(14) 0.9230(11) 0.5929(10) 0.066(4) Uani 1 1 d . . .
H69 H 0.9194 0.9449 0.6284 0.099 Uiso 1 1 calc R . .
H70 H 0.8288 0.8731 0.6448 0.099 Uiso 1 1 calc R . .
H71 H 0.8028 0.9961 0.5447 0.099 Uiso 1 1 calc R . .
C78 C 1.2273(11) 0.7012(10) 0.0224(7) 0.045(3) Uani 1 1 d . . .
H72 H 1.3139 0.6431 0.0157 0.054 Uiso 1 1 calc R . .
H73 H 1.2331 0.7796 0.0023 0.054 Uiso 1 1 calc R . .
C79 C 1.1277(12) 0.7142(10) -0.0507(8) 0.049(3) Uani 1 1 d . . .
H74 H 1.1178 0.6370 -0.0276 0.059 Uiso 1 1 calc R . .
H75 H 1.0423 0.7759 -0.0470 0.059 Uiso 1 1 calc R . .
C80 C 1.1682(12) 0.7500(10) -0.1631(8) 0.055(3) Uani 1 1 d . . .
H76 H 1.1017 0.7585 -0.2081 0.082 Uiso 1 1 calc R . .
H77 H 1.2514 0.6879 -0.1673 0.082 Uiso 1 1 calc R . .
H78 H 1.1774 0.8267 -0.1863 0.082 Uiso 1 1 calc R . .
O1 O 0.6478(9) 0.1811(7) 1.0711(5) 0.063(2) 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
N1 C1 1.381(14) . ?
N1 C4 1.397(15) . ?
N1 H1 0.8800 . ?
N2 C8 1.287(13) . ?
N2 C5 1.366(14) . ?
N3 C8 1.349(14) . ?
N3 C7 1.379(13) . ?
N4 C9 1.381(14) . ?
N4 C12 1.401(14) . ?
N4 H2 0.8800 . ?
N5 C13 1.351(13) . ?
N5 C16 1.369(12) . ?
N5 H3 0.8800 . ?
N6 C20 1.295(12) . ?
N6 C17 1.384(12) . ?
N7 C20 1.317(13) . ?
N7 C19 1.368(12) . ?
C81 C21 1.401(14) . ?
C81 C24 1.415(15) . ?
C81 H79 0.9500 . ?
N9 C30 1.394(12) . ?
N9 C38 1.400(12) . ?
N9 C44 1.490(12) . ?
N10 C28 1.369(13) . ?
N10 C32 1.374(13) . ?
N10 C47 1.654(18) . ?
N11 C36 1.377(13) . ?
N11 C40 1.387(12) . ?
N11 C50 1.509(12) . ?
N12 C59 1.374(12) . ?
N12 C55 1.420(12) . ?
N12 C72 1.460(12) . ?
N13 C63 1.389(12) . ?
N13 C66 1.426(12) . ?
N13 C75 1.456(12) . ?
N14 C70 1.371(12) . ?
N14 C57 1.411(12) . ?
N14 C78 1.470(11) . ?
Br1 C8 1.909(12) . ?
Br2 C20 1.914(11) . ?
C1 C2 1.362(19) . ?
C1 H5 0.9500 . ?
C2 C3 1.391(16) . ?
C2 H6 0.9500 . ?
C3 C4 1.406(15) . ?
C3 H7 0.9500 . ?
C4 C5 1.449(14) . ?
C5 C6 1.375(15) . ?
C6 C7 1.374(13) . ?
C6 H8 0.9500 . ?
C7 C9 1.432(14) . ?
C9 C10 1.367(13) . ?
C10 C11 1.420(16) . ?
C10 H9 0.9500 . ?
C11 C12 1.381(17) . ?
C11 H10 0.9500 . ?
C12 H11 0.9500 . ?
C13 C14 1.378(15) . ?
C13 H12 0.9500 . ?
C14 C15 1.402(15) . ?
C14 H13 0.9500 . ?
C15 C16 1.413(14) . ?
C15 H14 0.9500 . ?
C16 C17 1.467(14) . ?
C17 C18 1.373(14) . ?
C18 C19 1.405(13) . ?
C18 H15 0.9500 . ?
C19 C21 1.443(13) . ?
C21 N15 1.370(12) . ?
N15 C23 1.353(12) . ?
N15 H80 0.8800 . ?
C23 C24 1.380(14) . ?
C23 H17 0.9500 . ?
C24 H18 0.9500 . ?
C25 C30 1.401(14) . ?
C25 C26 1.414(15) . ?
C25 H19 0.9500 . ?
C26 C27 1.398(15) . ?
C26 H20 0.9500 . ?
C27 C28 1.410(15) . ?
C27 H21 0.9500 . ?
C28 C29 1.414(14) . ?
C29 C43 1.402(13) . ?
C29 C30 1.432(13) . ?
C31 C32 1.416(14) . ?
C31 C43 1.419(13) . ?
C31 C36 1.422(13) . ?
C32 C33 1.416(14) . ?
C33 C34 1.397(15) . ?
C33 H22 0.9500 . ?
C34 C35 1.403(15) . ?
C34 H23 0.9500 . ?
C35 C36 1.370(14) . ?
C35 H24 0.9500 . ?
C37 C42 1.368(13) . ?
C37 C38 1.382(14) . ?
C37 H25 0.9500 . ?
C38 C39 1.427(13) . ?
C39 C43 1.389(13) . ?
C39 C40 1.441(13) . ?
C40 C41 1.418(14) . ?
C41 C42 1.360(14) . ?
C41 H26 0.9500 . ?
C42 H27 0.9500 . ?
C44 C45 1.510(16) . ?
C44 H28 0.9900 . ?
C44 H29 0.9900 . ?
C45 C46 1.504(16) . ?
C45 H30 0.9900 . ?
C45 H31 0.9900 . ?
C46 H32 0.9800 . ?
C46 H33 0.9800 . ?
C46 H34 0.9800 . ?
C47 C48 1.40(2) . ?
C47 H35 0.9900 . ?
C47 H36 0.9900 . ?
C48 C49 1.70(2) . ?
C48 H37 0.9900 . ?
C48 H38 0.9900 . ?
C49 H39 0.9800 . ?
C49 H40 0.9800 . ?
C49 H41 0.9800 . ?
C50 C51 1.521(17) . ?
C50 H42 0.9900 . ?
C50 H43 0.9900 . ?
C51 C52 1.513(14) . ?
C51 H44 0.9900 . ?
C51 H45 0.9900 . ?
C52 H46 0.9800 . ?
C52 H47 0.9800 . ?
C52 H48 0.9800 . ?
C53 C54 1.377(14) . ?
C53 C58 1.379(14) . ?
C53 H49 0.9500 . ?
C54 C55 1.365(14) . ?
C54 H50 0.9500 . ?
C55 C56 1.412(13) . ?
C56 C71 1.397(13) . ?
C56 C57 1.422(13) . ?
C57 C58 1.395(14) . ?
C58 H51 0.9500 . ?
C59 C60 1.390(13) . ?
C59 C64 1.414(14) . ?
C60 C61 1.369(14) . ?
C60 H52 0.9500 . ?
C61 C62 1.381(14) . ?
C61 H53 0.9500 . ?
C62 C63 1.408(13) . ?
C62 H54 0.9500 . ?
C63 C64 1.396(14) . ?
C64 C71 1.437(13) . ?
C65 C66 1.380(14) . ?
C65 C71 1.399(13) . ?
C65 C70 1.435(13) . ?
C66 C67 1.391(14) . ?
C67 C68 1.383(14) . ?
C67 H55 0.9500 . ?
C68 C69 1.385(14) . ?
C68 H56 0.9500 . ?
C69 C70 1.410(14) . ?
C69 H57 0.9500 . ?
C72 C73 1.545(16) . ?
C72 H58 0.9900 . ?
C72 H59 0.9900 . ?
C73 C74 1.461(16) . ?
C73 H60 0.9900 . ?
C73 H61 0.9900 . ?
C74 H62 0.9800 . ?
C74 H63 0.9800 . ?
C74 H64 0.9800 . ?
C75 C76 1.509(14) . ?
C75 H65 0.9900 . ?
C75 H66 0.9900 . ?
C76 C77 1.539(14) . ?
C76 H67 0.9900 . ?
C76 H68 0.9900 . ?
C77 H69 0.9800 . ?
C77 H70 0.9800 . ?
C77 H71 0.9800 . ?
C78 C79 1.523(15) . ?
C78 H72 0.9900 . ?
C78 H73 0.9900 . ?
C79 C80 1.522(14) . ?
C79 H74 0.9900 . ?
C79 H75 0.9900 . ?
C80 H76 0.9800 . ?
C80 H77 0.9800 . ?
C80 H78 0.9800 . ?

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
C1 N1 C4 110.3(11) . . ?
C1 N1 H1 124.8 . . ?
C4 N1 H1 124.8 . . ?
C8 N2 C5 114.8(10) . . ?
C8 N3 C7 114.9(8) . . ?
C9 N4 C12 110.1(10) . . ?
C9 N4 H2 125.0 . . ?
C12 N4 H2 125.0 . . ?
C13 N5 C16 108.5(9) . . ?
C13 N5 H3 125.8 . . ?
C16 N5 H3 125.8 . . ?
C20 N6 C17 113.7(9) . . ?
C20 N7 C19 114.4(9) . . ?
C21 C81 C24 105.5(10) . . ?
C21 C81 H79 127.2 . . ?
C24 C81 H79 127.2 . . ?
C30 N9 C38 123.4(8) . . ?
C30 N9 C44 119.1(8) . . ?
C38 N9 C44 117.5(8) . . ?
C28 N10 C32 122.8(9) . . ?
C28 N10 C47 118.4(9) . . ?
C32 N10 C47 117.5(8) . . ?
C36 N11 C40 122.5(8) . . ?
C36 N11 C50 119.5(8) . . ?
C40 N11 C50 117.9(9) . . ?
C59 N12 C55 122.3(8) . . ?
C59 N12 C72 119.5(9) . . ?
C55 N12 C72 118.0(8) . . ?
C63 N13 C66 120.5(8) . . ?
C63 N13 C75 119.4(8) . . ?
C66 N13 C75 119.8(8) . . ?
C70 N14 C57 121.3(8) . . ?
C70 N14 C78 120.8(9) . . ?
C57 N14 C78 117.8(8) . . ?
C2 C1 N1 105.9(13) . . ?
C2 C1 H5 127.1 . . ?
N1 C1 H5 127.1 . . ?
C1 C2 C3 111.2(12) . . ?
C1 C2 H6 124.4 . . ?
C3 C2 H6 124.4 . . ?
C2 C3 C4 106.3(12) . . ?
C2 C3 H7 126.9 . . ?
C4 C3 H7 126.9 . . ?
N1 C4 C3 106.3(10) . . ?
N1 C4 C5 122.5(11) . . ?
C3 C4 C5 130.5(12) . . ?
N2 C5 C6 120.5(9) . . ?
N2 C5 C4 114.5(11) . . ?
C6 C5 C4 125.0(11) . . ?
C7 C6 C5 120.8(11) . . ?
C7 C6 H8 119.6 . . ?
C5 C6 H8 119.6 . . ?
C6 C7 N3 118.6(10) . . ?
C6 C7 C9 126.0(11) . . ?
N3 C7 C9 115.4(9) . . ?
N2 C8 N3 130.2(11) . . ?
N2 C8 Br1 116.7(9) . . ?
N3 C8 Br1 113.1(8) . . ?
C10 C9 N4 107.6(11) . . ?
C10 C9 C7 129.9(11) . . ?
N4 C9 C7 122.6(9) . . ?
C9 C10 C11 107.7(11) . . ?
C9 C10 H9 126.1 . . ?
C11 C10 H9 126.1 . . ?
C12 C11 C10 108.6(10) . . ?
C12 C11 H10 125.7 . . ?
C10 C11 H10 125.7 . . ?
C11 C12 N4 105.8(12) . . ?
C11 C12 H11 127.1 . . ?
N4 C12 H11 127.1 . . ?
N5 C13 C14 109.1(10) . . ?
N5 C13 H12 125.5 . . ?
C14 C13 H12 125.5 . . ?
C13 C14 C15 108.4(10) . . ?
C13 C14 H13 125.8 . . ?
C15 C14 H13 125.8 . . ?
C14 C15 C16 105.2(10) . . ?
C14 C15 H14 127.4 . . ?
C16 C15 H14 127.4 . . ?
N5 C16 C15 108.9(9) . . ?
N5 C16 C17 123.7(9) . . ?
C15 C16 C17 127.4(10) . . ?
C18 C17 N6 120.4(10) . . ?
C18 C17 C16 122.9(10) . . ?
N6 C17 C16 116.7(9) . . ?
C17 C18 C19 119.6(9) . . ?
C17 C18 H15 120.2 . . ?
C19 C18 H15 120.2 . . ?
N7 C19 C18 119.3(9) . . ?
N7 C19 C21 118.0(9) . . ?
C18 C19 C21 122.7(9) . . ?
N6 C20 N7 132.4(10) . . ?
N6 C20 Br2 113.1(8) . . ?
N7 C20 Br2 114.4(8) . . ?
N15 C21 C81 109.5(9) . . ?
N15 C21 C19 121.2(9) . . ?
C81 C21 C19 129.4(10) . . ?
C23 N15 C21 107.8(9) . . ?
C23 N15 H80 126.1 . . ?
C21 N15 H80 126.1 . . ?
N15 C23 C24 109.9(9) . . ?
N15 C23 H17 125.1 . . ?
C24 C23 H17 125.1 . . ?
C23 C24 C81 107.3(9) . . ?
C23 C24 H18 126.4 . . ?
C81 C24 H18 126.4 . . ?
C30 C25 C26 117.0(10) . . ?
C30 C25 H19 121.5 . . ?
C26 C25 H19 121.5 . . ?
C27 C26 C25 123.8(10) . . ?
C27 C26 H20 118.1 . . ?
C25 C26 H20 118.1 . . ?
C26 C27 C28 118.8(11) . . ?
C26 C27 H21 120.6 . . ?
C28 C27 H21 120.6 . . ?
N10 C28 C27 121.2(10) . . ?
N10 C28 C29 119.9(9) . . ?
C27 C28 C29 119.0(10) . . ?
C43 C29 C28 119.0(9) . . ?
C43 C29 C30 120.3(9) . . ?
C28 C29 C30 120.7(9) . . ?
N9 C30 C25 121.5(9) . . ?
N9 C30 C29 117.9(9) . . ?
C25 C30 C29 120.5(9) . . ?
C32 C31 C43 120.1(9) . . ?
C32 C31 C36 120.3(9) . . ?
C43 C31 C36 119.7(9) . . ?
N10 C32 C31 118.2(9) . . ?
N10 C32 C33 121.9(10) . . ?
C31 C32 C33 119.8(10) . . ?
C34 C33 C32 118.0(11) . . ?
C34 C33 H22 121.0 . . ?
C32 C33 H22 121.0 . . ?
C33 C34 C35 122.0(11) . . ?
C33 C34 H23 119.0 . . ?
C35 C34 H23 119.0 . . ?
C36 C35 C34 120.4(10) . . ?
C36 C35 H24 119.8 . . ?
C34 C35 H24 119.8 . . ?
C35 C36 N11 121.7(10) . . ?
C35 C36 C31 119.3(10) . . ?
N11 C36 C31 118.9(9) . . ?
C42 C37 C38 118.7(9) . . ?
C42 C37 H25 120.6 . . ?
C38 C37 H25 120.6 . . ?
C37 C38 N9 122.7(9) . . ?
C37 C38 C39 120.4(9) . . ?
N9 C38 C39 116.8(9) . . ?
C43 C39 C38 121.8(9) . . ?
C43 C39 C40 119.2(9) . . ?
C38 C39 C40 119.0(9) . . ?
N11 C40 C41 122.8(9) . . ?
N11 C40 C39 118.9(9) . . ?
C41 C40 C39 118.3(9) . . ?
C42 C41 C40 119.1(10) . . ?
C42 C41 H26 120.5 . . ?
C40 C41 H26 120.5 . . ?
C41 C42 C37 124.5(10) . . ?
C41 C42 H27 117.8 . . ?
C37 C42 H27 117.8 . . ?
C39 C43 C29 119.7(9) . . ?
C39 C43 C31 120.5(9) . . ?
C29 C43 C31 119.7(9) . . ?
N9 C44 C45 113.0(9) . . ?
N9 C44 H28 109.0 . . ?
C45 C44 H28 109.0 . . ?
N9 C44 H29 109.0 . . ?
C45 C44 H29 109.0 . . ?
H28 C44 H29 107.8 . . ?
C46 C45 C44 115.2(10) . . ?
C46 C45 H30 108.5 . . ?
C44 C45 H30 108.5 . . ?
C46 C45 H31 108.5 . . ?
C44 C45 H31 108.5 . . ?
H30 C45 H31 107.5 . . ?
C45 C46 H32 109.5 . . ?
C45 C46 H33 109.5 . . ?
H32 C46 H33 109.5 . . ?
C45 C46 H34 109.5 . . ?
H32 C46 H34 109.5 . . ?
H33 C46 H34 109.5 . . ?
C48 C47 N10 101.0(13) . . ?
C48 C47 H35 111.6 . . ?
N10 C47 H35 111.6 . . ?
C48 C47 H36 111.6 . . ?
N10 C47 H36 111.6 . . ?
H35 C47 H36 109.4 . . ?
C47 C48 C49 99.2(14) . . ?
C47 C48 H37 111.9 . . ?
C49 C48 H37 111.9 . . ?
C47 C48 H38 111.9 . . ?
C49 C48 H38 111.9 . . ?
H37 C48 H38 109.6 . . ?
C48 C49 H39 109.5 . . ?
C48 C49 H40 109.5 . . ?
H39 C49 H40 109.5 . . ?
C48 C49 H41 109.5 . . ?
H39 C49 H41 109.5 . . ?
H40 C49 H41 109.5 . . ?
N11 C50 C51 110.3(9) . . ?
N11 C50 H42 109.6 . . ?
C51 C50 H42 109.6 . . ?
N11 C50 H43 109.6 . . ?
C51 C50 H43 109.6 . . ?
H42 C50 H43 108.1 . . ?
C52 C51 C50 110.0(10) . . ?
C52 C51 H44 109.7 . . ?
C50 C51 H44 109.7 . . ?
C52 C51 H45 109.7 . . ?
C50 C51 H45 109.7 . . ?
H44 C51 H45 108.2 . . ?
C51 C52 H46 109.5 . . ?
C51 C52 H47 109.5 . . ?
H46 C52 H47 109.5 . . ?
C51 C52 H48 109.5 . . ?
H46 C52 H48 109.5 . . ?
H47 C52 H48 109.5 . . ?
C54 C53 C58 123.4(10) . . ?
C54 C53 H49 118.3 . . ?
C58 C53 H49 118.3 . . ?
C55 C54 C53 119.9(10) . . ?
C55 C54 H50 120.0 . . ?
C53 C54 H50 120.0 . . ?
C54 C55 C56 119.7(10) . . ?
C54 C55 N12 122.9(9) . . ?
C56 C55 N12 117.4(9) . . ?
C71 C56 C55 122.1(9) . . ?
C71 C56 C57 119.0(9) . . ?
C55 C56 C57 118.9(9) . . ?
C58 C57 N14 120.4(9) . . ?
C58 C57 C56 120.6(9) . . ?
N14 C57 C56 118.9(9) . . ?
C53 C58 C57 117.3(10) . . ?
C53 C58 H51 121.3 . . ?
C57 C58 H51 121.3 . . ?
N12 C59 C60 122.5(10) . . ?
N12 C59 C64 120.0(9) . . ?
C60 C59 C64 117.4(10) . . ?
C61 C60 C59 121.2(10) . . ?
C61 C60 H52 119.4 . . ?
C59 C60 H52 119.4 . . ?
C60 C61 C62 121.8(10) . . ?
C60 C61 H53 119.1 . . ?
C62 C61 H53 119.1 . . ?
C61 C62 C63 119.1(10) . . ?
C61 C62 H54 120.5 . . ?
C63 C62 H54 120.5 . . ?
N13 C63 C64 120.7(9) . . ?
N13 C63 C62 120.2(10) . . ?
C64 C63 C62 118.9(10) . . ?
C63 C64 C59 121.6(10) . . ?
C63 C64 C71 119.0(9) . . ?
C59 C64 C71 119.4(9) . . ?
C66 C65 C71 122.6(9) . . ?
C66 C65 C70 120.0(9) . . ?
C71 C65 C70 117.3(9) . . ?
C65 C66 C67 121.7(10) . . ?
C65 C66 N13 118.0(9) . . ?
C67 C66 N13 120.0(9) . . ?
C68 C67 C66 117.2(10) . . ?
C68 C67 H55 121.4 . . ?
C66 C67 H55 121.4 . . ?
C67 C68 C69 124.3(10) . . ?
C67 C68 H56 117.9 . . ?
C69 C68 H56 117.9 . . ?
C68 C69 C70 118.1(10) . . ?
C68 C69 H57 121.0 . . ?
C70 C69 H57 121.0 . . ?
N14 C70 C69 120.6(9) . . ?
N14 C70 C65 120.7(9) . . ?
C69 C70 C65 118.6(9) . . ?
C56 C71 C65 122.5(9) . . ?
C56 C71 C64 118.8(9) . . ?
C65 C71 C64 118.6(9) . . ?
N12 C72 C73 110.5(10) . . ?
N12 C72 H58 109.5 . . ?
C73 C72 H58 109.5 . . ?
N12 C72 H59 109.5 . . ?
C73 C72 H59 109.5 . . ?
H58 C72 H59 108.1 . . ?
C74 C73 C72 112.7(12) . . ?
C74 C73 H60 109.0 . . ?
C72 C73 H60 109.0 . . ?
C74 C73 H61 109.0 . . ?
C72 C73 H61 109.0 . . ?
H60 C73 H61 107.8 . . ?
C73 C74 H62 109.5 . . ?
C73 C74 H63 109.5 . . ?
H62 C74 H63 109.5 . . ?
C73 C74 H64 109.5 . . ?
H62 C74 H64 109.5 . . ?
H63 C74 H64 109.5 . . ?
N13 C75 C76 114.4(10) . . ?
N13 C75 H65 108.7 . . ?
C76 C75 H65 108.7 . . ?
N13 C75 H66 108.7 . . ?
C76 C75 H66 108.7 . . ?
H65 C75 H66 107.6 . . ?
C75 C76 C77 110.4(10) . . ?
C75 C76 H67 109.6 . . ?
C77 C76 H67 109.6 . . ?
C75 C76 H68 109.6 . . ?
C77 C76 H68 109.6 . . ?
H67 C76 H68 108.1 . . ?
C76 C77 H69 109.5 . . ?
C76 C77 H70 109.5 . . ?
H69 C77 H70 109.5 . . ?
C76 C77 H71 109.5 . . ?
H69 C77 H71 109.5 . . ?
H70 C77 H71 109.5 . . ?
N14 C78 C79 110.9(9) . . ?
N14 C78 H72 109.5 . . ?
C79 C78 H72 109.5 . . ?
N14 C78 H73 109.5 . . ?
C79 C78 H73 109.5 . . ?
H72 C78 H73 108.1 . . ?
C80 C79 C78 111.5(10) . . ?
C80 C79 H74 109.3 . . ?
C78 C79 H74 109.3 . . ?
C80 C79 H75 109.3 . . ?
C78 C79 H75 109.3 . . ?
H74 C79 H75 108.0 . . ?
C79 C80 H76 109.5 . . ?
C79 C80 H77 109.5 . . ?
H76 C80 H77 109.5 . . ?
C79 C80 H78 109.5 . . ?
H76 C80 H78 109.5 . . ?
H77 C80 H78 109.5 . . ?

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
C4 N1 C1 C2 1.1(14) . . . . ?
N1 C1 C2 C3 -0.8(16) . . . . ?
C1 C2 C3 C4 0.1(15) . . . . ?
C1 N1 C4 C3 -1.1(13) . . . . ?
C1 N1 C4 C5 -172.7(10) . . . . ?
C2 C3 C4 N1 0.6(13) . . . . ?
C2 C3 C4 C5 171.3(12) . . . . ?
C8 N2 C5 C6 5.2(15) . . . . ?
C8 N2 C5 C4 -176.3(9) . . . . ?
N1 C4 C5 N2 175.4(10) . . . . ?
C3 C4 C5 N2 5.9(17) . . . . ?
N1 C4 C5 C6 -6.2(17) . . . . ?
C3 C4 C5 C6 -175.7(11) . . . . ?
N2 C5 C6 C7 -5.5(16) . . . . ?
C4 C5 C6 C7 176.2(11) . . . . ?
C5 C6 C7 N3 2.1(15) . . . . ?
C5 C6 C7 C9 -176.9(10) . . . . ?
C8 N3 C7 C6 1.1(13) . . . . ?
C8 N3 C7 C9 -179.7(9) . . . . ?
C5 N2 C8 N3 -1.9(16) . . . . ?
C5 N2 C8 Br1 178.6(7) . . . . ?
C7 N3 C8 N2 -1.3(16) . . . . ?
C7 N3 C8 Br1 178.3(6) . . . . ?
C12 N4 C9 C10 -0.7(12) . . . . ?
C12 N4 C9 C7 179.3(9) . . . . ?
C6 C7 C9 C10 157.4(12) . . . . ?
N3 C7 C9 C10 -21.6(16) . . . . ?
C6 C7 C9 N4 -22.6(16) . . . . ?
N3 C7 C9 N4 158.4(10) . . . . ?
N4 C9 C10 C11 3.4(13) . . . . ?
C7 C9 C10 C11 -176.6(11) . . . . ?
C9 C10 C11 C12 -5.0(14) . . . . ?
C10 C11 C12 N4 4.4(13) . . . . ?
C9 N4 C12 C11 -2.4(12) . . . . ?
C16 N5 C13 C14 -0.6(13) . . . . ?
N5 C13 C14 C15 0.5(14) . . . . ?
C13 C14 C15 C16 -0.2(14) . . . . ?
C13 N5 C16 C15 0.4(13) . . . . ?
C13 N5 C16 C17 179.0(11) . . . . ?
C14 C15 C16 N5 -0.1(14) . . . . ?
C14 C15 C16 C17 -178.6(11) . . . . ?
C20 N6 C17 C18 -1.6(15) . . . . ?
C20 N6 C17 C16 178.3(10) . . . . ?
N5 C16 C17 C18 1.0(18) . . . . ?
C15 C16 C17 C18 179.3(11) . . . . ?
N5 C16 C17 N6 -178.9(10) . . . . ?
C15 C16 C17 N6 -0.6(18) . . . . ?
N6 C17 C18 C19 2.7(16) . . . . ?
C16 C17 C18 C19 -177.2(10) . . . . ?
C20 N7 C19 C18 3.3(15) . . . . ?
C20 N7 C19 C21 -178.4(10) . . . . ?
C17 C18 C19 N7 -3.6(16) . . . . ?
C17 C18 C19 C21 178.2(10) . . . . ?
C17 N6 C20 N7 1.7(18) . . . . ?
C17 N6 C20 Br2 179.3(7) . . . . ?
C19 N7 C20 N6 -2.6(18) . . . . ?
C19 N7 C20 Br2 179.8(8) . . . . ?
C24 C81 C21 N15 -1.3(13) . . . . ?
C24 C81 C21 C19 179.0(11) . . . . ?
N7 C19 C21 N15 -4.1(16) . . . . ?
C18 C19 C21 N15 174.1(10) . . . . ?
N7 C19 C21 C81 175.6(11) . . . . ?
C18 C19 C21 C81 -6.2(19) . . . . ?
C81 C21 N15 C23 1.6(13) . . . . ?
C19 C21 N15 C23 -178.7(10) . . . . ?
C21 N15 C23 C24 -1.3(14) . . . . ?
N15 C23 C24 C81 0.4(14) . . . . ?
C21 C81 C24 C23 0.6(14) . . . . ?
C30 C25 C26 C27 -0.8(19) . . . . ?
C25 C26 C27 C28 -2(2) . . . . ?
C32 N10 C28 C27 -172.9(12) . . . . ?
C47 N10 C28 C27 20.6(19) . . . . ?
C32 N10 C28 C29 7(2) . . . . ?
C47 N10 C28 C29 -159.3(12) . . . . ?
C26 C27 C28 N10 -175.2(12) . . . . ?
C26 C27 C28 C29 5(2) . . . . ?
N10 C28 C29 C43 -2.5(19) . . . . ?
C27 C28 C29 C43 177.5(11) . . . . ?
N10 C28 C29 C30 175.2(11) . . . . ?
C27 C28 C29 C30 -4.7(19) . . . . ?
C38 N9 C30 C25 178.9(11) . . . . ?
C44 N9 C30 C25 -1.9(16) . . . . ?
C38 N9 C30 C29 -2.6(16) . . . . ?
C44 N9 C30 C29 176.7(9) . . . . ?
C26 C25 C30 N9 179.4(10) . . . . ?
C26 C25 C30 C29 0.9(17) . . . . ?
C43 C29 C30 N9 1.1(16) . . . . ?
C28 C29 C30 N9 -176.7(11) . . . . ?
C43 C29 C30 C25 179.6(11) . . . . ?
C28 C29 C30 C25 1.9(18) . . . . ?
C28 N10 C32 C31 -7.5(18) . . . . ?
C47 N10 C32 C31 159.1(11) . . . . ?
C28 N10 C32 C33 176.2(12) . . . . ?
C47 N10 C32 C33 -17.2(18) . . . . ?
C43 C31 C32 N10 3.2(17) . . . . ?
C36 C31 C32 N10 -175.7(11) . . . . ?
C43 C31 C32 C33 179.6(10) . . . . ?
C36 C31 C32 C33 0.6(17) . . . . ?
N10 C32 C33 C34 176.7(11) . . . . ?
C31 C32 C33 C34 0.4(17) . . . . ?
C32 C33 C34 C35 0.0(18) . . . . ?
C33 C34 C35 C36 -1.5(19) . . . . ?
C34 C35 C36 N11 -176.4(11) . . . . ?
C34 C35 C36 C31 2.6(18) . . . . ?
C40 N11 C36 C35 -176.6(11) . . . . ?
C50 N11 C36 C35 6.4(17) . . . . ?
C40 N11 C36 C31 4.4(17) . . . . ?
C50 N11 C36 C31 -172.6(10) . . . . ?
C32 C31 C36 C35 -2.1(17) . . . . ?
C43 C31 C36 C35 178.9(11) . . . . ?
C32 C31 C36 N11 176.9(10) . . . . ?
C43 C31 C36 N11 -2.1(16) . . . . ?
C42 C37 C38 N9 178.9(11) . . . . ?
C42 C37 C38 C39 -1.1(18) . . . . ?
C30 N9 C38 C37 -177.9(11) . . . . ?
C44 N9 C38 C37 2.9(17) . . . . ?
C30 N9 C38 C39 2.1(16) . . . . ?
C44 N9 C38 C39 -177.1(10) . . . . ?
C37 C38 C39 C43 179.8(11) . . . . ?
N9 C38 C39 C43 -0.2(17) . . . . ?
C37 C38 C39 C40 -1.3(17) . . . . ?
N9 C38 C39 C40 178.7(10) . . . . ?
C36 N11 C40 C41 176.5(11) . . . . ?
C50 N11 C40 C41 -6.4(17) . . . . ?
C36 N11 C40 C39 -4.5(17) . . . . ?
C50 N11 C40 C39 172.5(10) . . . . ?
C43 C39 C40 N11 2.3(17) . . . . ?
C38 C39 C40 N11 -176.7(10) . . . . ?
C43 C39 C40 C41 -178.7(11) . . . . ?
C38 C39 C40 C41 2.4(17) . . . . ?
N11 C40 C41 C42 177.8(11) . . . . ?
C39 C40 C41 C42 -1.2(18) . . . . ?
C40 C41 C42 C37 -1(2) . . . . ?
C38 C37 C42 C41 2(2) . . . . ?
C38 C39 C43 C29 -1.2(18) . . . . ?
C40 C39 C43 C29 179.9(10) . . . . ?
C38 C39 C43 C31 178.7(11) . . . . ?
C40 C39 C43 C31 -0.2(17) . . . . ?
C28 C29 C43 C39 178.5(11) . . . . ?
C30 C29 C43 C39 0.7(17) . . . . ?
C28 C29 C43 C31 -1.4(18) . . . . ?
C30 C29 C43 C31 -179.2(10) . . . . ?
C32 C31 C43 C39 -178.9(11) . . . . ?
C36 C31 C43 C39 0.1(17) . . . . ?
C32 C31 C43 C29 1.0(17) . . . . ?
C36 C31 C43 C29 -180.0(10) . . . . ?
C30 N9 C44 C45 -100.5(11) . . . . ?
C38 N9 C44 C45 78.8(12) . . . . ?
N9 C44 C45 C46 64.9(13) . . . . ?
C28 N10 C47 C48 -95.9(13) . . . . ?
C32 N10 C47 C48 96.9(13) . . . . ?
N10 C47 C48 C49 -177.4(8) . . . . ?
C36 N11 C50 C51 -92.1(12) . . . . ?
C40 N11 C50 C51 90.8(12) . . . . ?
N11 C50 C51 C52 179.3(9) . . . . ?
C58 C53 C54 C55 -0.3(19) . . . . ?
C53 C54 C55 C56 1.5(17) . . . . ?
C53 C54 C55 N12 179.9(10) . . . . ?
C59 N12 C55 C54 -177.0(11) . . . . ?
C72 N12 C55 C54 -1.5(16) . . . . ?
C59 N12 C55 C56 1.4(16) . . . . ?
C72 N12 C55 C56 176.9(10) . . . . ?
C54 C55 C56 C71 178.4(11) . . . . ?
N12 C55 C56 C71 -0.1(16) . . . . ?
C54 C55 C56 C57 -2.7(17) . . . . ?
N12 C55 C56 C57 178.8(10) . . . . ?
C70 N14 C57 C58 173.7(10) . . . . ?
C78 N14 C57 C58 -2.1(15) . . . . ?
C70 N14 C57 C56 -4.2(15) . . . . ?
C78 N14 C57 C56 180.0(9) . . . . ?
C71 C56 C57 C58 -178.3(10) . . . . ?
C55 C56 C57 C58 2.8(17) . . . . ?
C71 C56 C57 N14 -0.4(16) . . . . ?
C55 C56 C57 N14 -179.3(9) . . . . ?
C54 C53 C58 C57 0.3(18) . . . . ?
N14 C57 C58 C53 -179.4(10) . . . . ?
C56 C57 C58 C53 -1.5(17) . . . . ?
C55 N12 C59 C60 175.7(11) . . . . ?
C72 N12 C59 C60 0.2(17) . . . . ?
C55 N12 C59 C64 -1.4(17) . . . . ?
C72 N12 C59 C64 -176.9(10) . . . . ?
N12 C59 C60 C61 178.7(11) . . . . ?
C64 C59 C60 C61 -4.2(18) . . . . ?
C59 C60 C61 C62 3.3(19) . . . . ?
C60 C61 C62 C63 -0.1(18) . . . . ?
C66 N13 C63 C64 -8.6(15) . . . . ?
C75 N13 C63 C64 176.7(10) . . . . ?
C66 N13 C63 C62 177.6(10) . . . . ?
C75 N13 C63 C62 2.8(15) . . . . ?
C61 C62 C63 N13 172.1(10) . . . . ?
C61 C62 C63 C64 -1.8(17) . . . . ?
N13 C63 C64 C59 -173.2(10) . . . . ?
C62 C63 C64 C59 0.8(17) . . . . ?
N13 C63 C64 C71 6.1(16) . . . . ?
C62 C63 C64 C71 -179.9(10) . . . . ?
N12 C59 C64 C63 179.4(10) . . . . ?
C60 C59 C64 C63 2.2(18) . . . . ?
N12 C59 C64 C71 0.1(17) . . . . ?
C60 C59 C64 C71 -177.1(10) . . . . ?
C71 C65 C66 C67 -176.0(10) . . . . ?
C70 C65 C66 C67 1.7(16) . . . . ?
C71 C65 C66 N13 -1.6(16) . . . . ?
C70 C65 C66 N13 176.1(9) . . . . ?
C63 N13 C66 C65 6.2(14) . . . . ?
C75 N13 C66 C65 -179.1(9) . . . . ?
C63 N13 C66 C67 -179.3(9) . . . . ?
C75 N13 C66 C67 -4.6(15) . . . . ?
C65 C66 C67 C68 -0.6(16) . . . . ?
N13 C66 C67 C68 -174.9(10) . . . . ?
C66 C67 C68 C69 0.4(18) . . . . ?
C67 C68 C69 C70 -1.3(18) . . . . ?
C57 N14 C70 C69 -172.2(9) . . . . ?
C78 N14 C70 C69 3.5(15) . . . . ?
C57 N14 C70 C65 5.9(15) . . . . ?
C78 N14 C70 C65 -178.5(9) . . . . ?
C68 C69 C70 N14 -179.6(10) . . . . ?
C68 C69 C70 C65 2.3(16) . . . . ?
C66 C65 C70 N14 179.4(9) . . . . ?
C71 C65 C70 N14 -2.8(15) . . . . ?
C66 C65 C70 C69 -2.5(16) . . . . ?
C71 C65 C70 C69 175.3(10) . . . . ?
C55 C56 C71 C65 -177.7(10) . . . . ?
C57 C56 C71 C65 3.5(16) . . . . ?
C55 C56 C71 C64 -1.1(16) . . . . ?
C57 C56 C71 C64 180.0(10) . . . . ?
C66 C65 C71 C56 175.9(10) . . . . ?
C70 C65 C71 C56 -1.9(16) . . . . ?
C66 C65 C71 C64 -0.7(16) . . . . ?
C70 C65 C71 C64 -178.4(10) . . . . ?
C63 C64 C71 C56 -178.2(10) . . . . ?
C59 C64 C71 C56 1.1(16) . . . . ?
C63 C64 C71 C65 -1.5(16) . . . . ?
C59 C64 C71 C65 177.8(10) . . . . ?
C59 N12 C72 C73 84.4(12) . . . . ?
C55 N12 C72 C73 -91.2(12) . . . . ?
N12 C72 C73 C74 -163.0(11) . . . . ?
C63 N13 C75 C76 83.9(12) . . . . ?
C66 N13 C75 C76 -90.9(12) . . . . ?
N13 C75 C76 C77 -170.5(9) . . . . ?
C70 N14 C78 C79 -90.3(11) . . . . ?
C57 N14 C78 C79 85.5(12) . . . . ?
N14 C78 C79 C80 -176.5(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Cl1 0.88 2.27 3.105(11) 157.9 .
N4 H2 O1 0.88 1.92 2.773(11) 161.5 .
N5 H3 Cl2 0.88 2.44 3.316(9) 175.1 .
N15 H80 Cl1 0.88 2.49 3.233(9) 142.1 .

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        65.00
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.831
_refine_diff_density_min         -1.342
_refine_diff_density_rms         0.096
