# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013


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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
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data_19
_database_code_depnum_ccdc_archive 'CCDC 924454'
#TrackingRef 'compound 19.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3-bromo-N-(2-(3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl)-4
-chloro-6-methylphenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole
-5-carboxamide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H14 Br2 Cl2 N6 O2'
_chemical_formula_weight         649.13
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   9.2290(18)
_cell_length_b                   11.142(2)
_cell_length_c                   12.526(3)
_cell_angle_alpha                76.53(3)
_cell_angle_beta                 80.97(3)
_cell_angle_gamma                86.17(3)
_cell_volume                     1236.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      10
_cell_measurement_theta_max      14
_exptl_crystal_description       block
_exptl_crystal_colour            colourlrss
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    3.530
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.5387
_exptl_absorpt_correction_T_max  0.7191
_exptl_absorpt_process_details   '(M. Takahashi, et al., 1989)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius cad4'
_diffrn_measurement_method       \w/2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            4844
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_sigmaI/netI    0.0817
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.38
_reflns_number_total             4538
_reflns_number_gt                2523
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CAD4 Software(Enraf-Nonius,1985)'
_computing_cell_refinement       'CAD4 Software'
_computing_data_reduction        'XCAD4(Harms & Wocadlo,1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0900P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         4538
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1713
_refine_ls_wR_factor_gt          0.1490
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.49119(9) 0.51860(10) 0.82413(9) 0.0785(4) Uani 1 1 d . . .
Cl1 Cl 0.9543(2) 0.7139(2) 0.5333(2) 0.0752(7) Uani 1 1 d . . .
N1 N 0.9153(6) 0.5486(5) 0.7540(5) 0.0432(15) Uani 1 1 d . . .
O1 O 1.1470(5) 0.6663(5) 0.8131(4) 0.0519(14) Uani 1 1 d . . .
C1 C 1.0704(8) 0.5945(7) 0.5774(6) 0.0471(19) Uani 1 1 d . . .
N2 N 1.1297(7) 0.4277(6) 0.7244(5) 0.0526(17) Uani 1 1 d . . .
Br2 Br 0.15787(8) 0.94492(9) 0.57412(7) 0.0614(3) Uani 1 1 d . . .
Cl2 Cl 1.36854(19) 1.1760(2) 0.91422(17) 0.0572(6) Uani 1 1 d . . .
O2 O 0.8951(5) 1.1617(5) 0.7487(4) 0.0531(14) Uani 1 1 d . . .
C2 C 1.1964(9) 0.5672(8) 0.5086(6) 0.057(2) Uani 1 1 d . . .
H2B H 1.2194 0.6131 0.4363 0.068 Uiso 1 1 calc R . .
N3 N 0.7848(6) 0.5040(6) 0.7441(5) 0.0496(16) Uani 1 1 d . . .
C3 C 1.2831(9) 0.4724(9) 0.5508(8) 0.066(2) Uani 1 1 d . . .
H3B H 1.3684 0.4525 0.5072 0.079 Uiso 1 1 calc R . .
N4 N 0.9764(5) 0.7909(5) 0.8885(4) 0.0385(14) Uani 1 1 d . . .
H4A H 0.8849 0.7975 0.9145 0.046 Uiso 1 1 calc R . .
C4 C 1.2486(9) 0.4049(8) 0.6561(7) 0.061(2) Uani 1 1 d . . .
H4B H 1.3114 0.3394 0.6818 0.073 Uiso 1 1 calc R . .
N5 N 0.8031(5) 0.9788(5) 0.7842(4) 0.0354(13) Uani 1 1 d . . .
C5 C 1.0442(7) 0.5224(7) 0.6821(6) 0.0425(19) Uani 1 1 d . . .
C6 C 0.6877(8) 0.5540(7) 0.8115(6) 0.0491(19) Uani 1 1 d . . .
N6 N 0.7621(6) 1.1755(6) 0.7023(5) 0.0540(17) Uani 1 1 d . . .
C7 C 0.7479(7) 0.6296(7) 0.8670(6) 0.0436(18) Uani 1 1 d . . .
H7A H 0.7004 0.6722 0.9188 0.052 Uiso 1 1 calc R . .
C8 C 0.8976(7) 0.6251(6) 0.8252(6) 0.0383(17) Uani 1 1 d . . .
C9 C 1.0205(7) 0.6947(7) 0.8420(5) 0.0397(17) Uani 1 1 d . . .
C10 C 1.0706(6) 0.8816(7) 0.8972(5) 0.0320(16) Uani 1 1 d . . .
C11 C 1.0381(6) 1.0049(7) 0.8506(5) 0.0330(16) Uani 1 1 d . . .
C12 C 1.1307(7) 1.0972(7) 0.8566(5) 0.0358(16) Uani 1 1 d . . .
H12A H 1.1116 1.1799 0.8254 0.043 Uiso 1 1 calc R . .
C13 C 1.2503(7) 1.0610(7) 0.9103(5) 0.0376(17) Uani 1 1 d . . .
C14 C 1.2784(7) 0.9423(7) 0.9577(6) 0.0407(18) Uani 1 1 d . . .
H14A H 1.3612 0.9225 0.9928 0.049 Uiso 1 1 calc R . .
C15 C 1.1890(7) 0.8493(7) 0.9560(5) 0.0376(17) Uani 1 1 d . . .
C16 C 1.2182(8) 0.7216(8) 1.0184(6) 0.057(2) Uani 1 1 d . . .
H16A H 1.1467 0.6679 1.0085 0.086 Uiso 1 1 calc R . .
H16B H 1.2119 0.7206 1.0959 0.086 Uiso 1 1 calc R . .
H16C H 1.3146 0.6938 0.9913 0.086 Uiso 1 1 calc R . .
C17 C 0.9106(6) 1.0422(7) 0.7954(5) 0.0319(15) Uani 1 1 d . . .
C18 C 0.7165(7) 1.0647(7) 0.7254(5) 0.0346(16) Uani 1 1 d . . .
C19 C 0.5806(7) 1.0350(7) 0.6902(5) 0.0383(17) Uani 1 1 d . . .
C20 C 0.5283(7) 0.9172(7) 0.7228(6) 0.0465(19) Uani 1 1 d . . .
H20A H 0.5783 0.8559 0.7684 0.056 Uiso 1 1 calc R . .
C21 C 0.4025(7) 0.8893(7) 0.6884(6) 0.0487(19) Uani 1 1 d . . .
H21A H 0.3671 0.8097 0.7101 0.058 Uiso 1 1 calc R . .
C22 C 0.3305(7) 0.9817(8) 0.6213(5) 0.0405(18) Uani 1 1 d . . .
C23 C 0.3787(7) 1.0977(8) 0.5884(6) 0.052(2) Uani 1 1 d . . .
H23A H 0.3279 1.1584 0.5428 0.063 Uiso 1 1 calc R . .
C24 C 0.5080(8) 1.1262(7) 0.6241(6) 0.051(2) Uani 1 1 d . . .
H24A H 0.5427 1.2060 0.6027 0.061 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0371(5) 0.1033(8) 0.1044(8) -0.0380(6) -0.0101(5) -0.0165(5)
Cl1 0.0655(13) 0.0777(17) 0.0823(17) -0.0017(13) -0.0327(12) -0.0091(12)
N1 0.037(3) 0.058(4) 0.040(4) -0.024(3) -0.001(3) -0.008(3)
O1 0.027(2) 0.077(4) 0.061(3) -0.039(3) -0.002(2) 0.001(2)
C1 0.057(5) 0.048(5) 0.040(5) -0.010(4) -0.014(4) -0.013(4)
N2 0.044(4) 0.059(4) 0.056(4) -0.021(4) -0.002(3) 0.013(3)
Br2 0.0317(4) 0.1122(8) 0.0511(5) -0.0319(5) -0.0153(3) -0.0091(4)
Cl2 0.0362(9) 0.0830(15) 0.0641(13) -0.0307(11) -0.0154(9) -0.0159(9)
O2 0.045(3) 0.056(4) 0.064(4) -0.009(3) -0.030(3) -0.008(3)
C2 0.057(5) 0.081(7) 0.033(4) -0.019(4) 0.010(4) -0.023(5)
N3 0.042(3) 0.063(4) 0.053(4) -0.024(3) -0.013(3) -0.013(3)
C3 0.046(5) 0.089(7) 0.068(7) -0.036(6) 0.008(5) -0.012(5)
N4 0.022(3) 0.053(4) 0.043(4) -0.017(3) -0.004(2) 0.001(3)
C4 0.058(5) 0.075(6) 0.057(6) -0.032(5) -0.013(5) 0.014(5)
N5 0.025(3) 0.055(4) 0.029(3) -0.012(3) -0.009(2) -0.001(3)
C5 0.037(4) 0.065(5) 0.034(4) -0.027(4) 0.000(3) -0.014(4)
C6 0.040(4) 0.055(5) 0.057(5) -0.020(4) -0.010(4) -0.004(4)
N6 0.044(3) 0.052(4) 0.071(5) -0.003(3) -0.041(3) -0.001(3)
C7 0.033(4) 0.048(5) 0.050(5) -0.014(4) -0.005(3) 0.000(3)
C8 0.033(4) 0.040(4) 0.043(4) -0.010(3) -0.009(3) 0.005(3)
C9 0.031(4) 0.061(5) 0.031(4) -0.016(4) -0.007(3) -0.007(3)
C10 0.023(3) 0.056(5) 0.020(3) -0.013(3) -0.004(3) -0.007(3)
C11 0.023(3) 0.058(5) 0.019(3) -0.013(3) -0.002(3) 0.001(3)
C12 0.031(3) 0.052(5) 0.026(4) -0.013(3) -0.002(3) -0.006(3)
C13 0.027(3) 0.065(6) 0.028(4) -0.022(4) -0.004(3) -0.010(3)
C14 0.027(3) 0.062(6) 0.037(4) -0.018(4) -0.009(3) 0.004(3)
C15 0.032(3) 0.055(5) 0.030(4) -0.018(4) -0.006(3) 0.002(3)
C16 0.049(4) 0.081(7) 0.047(5) -0.022(5) -0.017(4) 0.012(4)
C17 0.026(3) 0.043(5) 0.031(4) -0.016(3) -0.006(3) 0.002(3)
C18 0.030(3) 0.046(5) 0.031(4) -0.011(3) -0.007(3) -0.003(3)
C19 0.030(3) 0.059(5) 0.029(4) -0.012(4) -0.012(3) 0.005(3)
C20 0.032(4) 0.059(5) 0.046(5) -0.003(4) -0.015(3) 0.003(4)
C21 0.042(4) 0.061(5) 0.046(5) -0.014(4) -0.011(4) -0.011(4)
C22 0.025(3) 0.074(6) 0.028(4) -0.023(4) -0.006(3) 0.004(4)
C23 0.032(4) 0.075(6) 0.056(5) -0.020(4) -0.021(4) 0.010(4)
C24 0.047(4) 0.052(5) 0.055(5) -0.014(4) -0.011(4) 0.001(4)
_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C6 1.856(7) . ?
Cl1 C1 1.696(8) . ?
N1 C8 1.356(8) . ?
N1 N3 1.367(7) . ?
N1 C5 1.433(8) . ?
O1 C9 1.211(7) . ?
C1 C5 1.364(10) . ?
C1 C2 1.395(10) . ?
N2 C4 1.330(9) . ?
N2 C5 1.332(9) . ?
Br2 C22 1.884(6) . ?
Cl2 C13 1.752(7) . ?
O2 C17 1.333(8) . ?
O2 N6 1.423(7) . ?
C2 C3 1.340(11) . ?
C2 H2B 0.9300 . ?
N3 C6 1.320(9) . ?
C3 C4 1.358(11) . ?
C3 H3B 0.9300 . ?
N4 C9 1.346(9) . ?
N4 C10 1.410(8) . ?
N4 H4A 0.8600 . ?
C4 H4B 0.9300 . ?
N5 C17 1.298(8) . ?
N5 C18 1.361(8) . ?
C6 C7 1.399(10) . ?
N6 C18 1.284(9) . ?
C7 C8 1.400(9) . ?
C7 H7A 0.9300 . ?
C8 C9 1.483(9) . ?
C10 C15 1.394(9) . ?
C10 C11 1.394(9) . ?
C11 C12 1.403(9) . ?
C11 C17 1.446(8) . ?
C12 C13 1.371(9) . ?
C12 H12A 0.9300 . ?
C13 C14 1.344(10) . ?
C14 C15 1.373(9) . ?
C14 H14A 0.9300 . ?
C15 C16 1.485(10) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 C19 1.474(9) . ?
C19 C24 1.364(10) . ?
C19 C20 1.378(10) . ?
C20 C21 1.377(9) . ?
C20 H20A 0.9300 . ?
C21 C22 1.374(10) . ?
C21 H21A 0.9300 . ?
C22 C23 1.345(11) . ?
C23 C24 1.417(10) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 N3 112.0(5) . . ?
C8 N1 C5 129.1(6) . . ?
N3 N1 C5 118.4(5) . . ?
C5 C1 C2 117.7(7) . . ?
C5 C1 Cl1 120.9(6) . . ?
C2 C1 Cl1 121.4(6) . . ?
C4 N2 C5 115.2(7) . . ?
C17 O2 N6 106.3(5) . . ?
C3 C2 C1 117.4(8) . . ?
C3 C2 H2B 121.3 . . ?
C1 C2 H2B 121.3 . . ?
C6 N3 N1 103.6(5) . . ?
C2 C3 C4 121.1(8) . . ?
C2 C3 H3B 119.4 . . ?
C4 C3 H3B 119.4 . . ?
C9 N4 C10 124.1(5) . . ?
C9 N4 H4A 117.9 . . ?
C10 N4 H4A 117.9 . . ?
N2 C4 C3 123.4(8) . . ?
N2 C4 H4B 118.3 . . ?
C3 C4 H4B 118.3 . . ?
C17 N5 C18 103.7(6) . . ?
N2 C5 C1 125.2(7) . . ?
N2 C5 N1 116.2(6) . . ?
C1 C5 N1 118.6(7) . . ?
N3 C6 C7 114.3(6) . . ?
N3 C6 Br1 118.6(5) . . ?
C7 C6 Br1 127.0(6) . . ?
C18 N6 O2 103.2(5) . . ?
C6 C7 C8 102.7(6) . . ?
C6 C7 H7A 128.6 . . ?
C8 C7 H7A 128.6 . . ?
N1 C8 C7 107.3(6) . . ?
N1 C8 C9 122.4(6) . . ?
C7 C8 C9 130.2(6) . . ?
O1 C9 N4 125.1(6) . . ?
O1 C9 C8 121.3(6) . . ?
N4 C9 C8 113.6(6) . . ?
C15 C10 C11 120.8(6) . . ?
C15 C10 N4 120.7(6) . . ?
C11 C10 N4 118.4(5) . . ?
C10 C11 C12 119.8(6) . . ?
C10 C11 C17 122.2(6) . . ?
C12 C11 C17 118.0(6) . . ?
C13 C12 C11 117.5(7) . . ?
C13 C12 H12A 121.2 . . ?
C11 C12 H12A 121.2 . . ?
C14 C13 C12 122.2(6) . . ?
C14 C13 Cl2 120.4(5) . . ?
C12 C13 Cl2 117.4(6) . . ?
C13 C14 C15 122.3(6) . . ?
C13 C14 H14A 118.9 . . ?
C15 C14 H14A 118.9 . . ?
C14 C15 C10 117.2(7) . . ?
C14 C15 C16 119.7(6) . . ?
C10 C15 C16 123.0(6) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N5 C17 O2 112.1(5) . . ?
N5 C17 C11 131.0(7) . . ?
O2 C17 C11 116.8(6) . . ?
N6 C18 N5 114.7(6) . . ?
N6 C18 C19 121.8(6) . . ?
N5 C18 C19 123.5(6) . . ?
C24 C19 C20 120.4(6) . . ?
C24 C19 C18 118.8(7) . . ?
C20 C19 C18 120.7(6) . . ?
C21 C20 C19 120.6(7) . . ?
C21 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
C22 C21 C20 118.5(7) . . ?
C22 C21 H21A 120.7 . . ?
C20 C21 H21A 120.7 . . ?
C23 C22 C21 122.3(6) . . ?
C23 C22 Br2 118.8(5) . . ?
C21 C22 Br2 118.9(6) . . ?
C22 C23 C24 119.1(7) . . ?
C22 C23 H23A 120.4 . . ?
C24 C23 H23A 120.4 . . ?
C19 C24 C23 119.1(7) . . ?
C19 C24 H24A 120.5 . . ?
C23 C24 H24A 120.5 . . ?
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
C5 C1 C2 C3 -0.3(10) . . . . ?
Cl1 C1 C2 C3 179.0(6) . . . . ?
C8 N1 N3 C6 -0.6(8) . . . . ?
C5 N1 N3 C6 -173.6(7) . . . . ?
C1 C2 C3 C4 0.6(12) . . . . ?
C5 N2 C4 C3 0.4(12) . . . . ?
C2 C3 C4 N2 -0.6(13) . . . . ?
C4 N2 C5 C1 -0.1(11) . . . . ?
C4 N2 C5 N1 179.9(6) . . . . ?
C2 C1 C5 N2 0.1(11) . . . . ?
Cl1 C1 C5 N2 -179.2(6) . . . . ?
C2 C1 C5 N1 -179.9(6) . . . . ?
Cl1 C1 C5 N1 0.8(9) . . . . ?
C8 N1 C5 N2 90.6(9) . . . . ?
N3 N1 C5 N2 -97.8(8) . . . . ?
C8 N1 C5 C1 -89.4(9) . . . . ?
N3 N1 C5 C1 82.2(8) . . . . ?
N1 N3 C6 C7 -0.5(9) . . . . ?
N1 N3 C6 Br1 179.7(5) . . . . ?
C17 O2 N6 C18 -0.7(7) . . . . ?
N3 C6 C7 C8 1.3(9) . . . . ?
Br1 C6 C7 C8 -178.9(6) . . . . ?
N3 N1 C8 C7 1.4(8) . . . . ?
C5 N1 C8 C7 173.5(7) . . . . ?
N3 N1 C8 C9 -174.1(6) . . . . ?
C5 N1 C8 C9 -2.0(12) . . . . ?
C6 C7 C8 N1 -1.6(8) . . . . ?
C6 C7 C8 C9 173.4(7) . . . . ?
C10 N4 C9 O1 8.5(11) . . . . ?
C10 N4 C9 C8 -169.9(6) . . . . ?
N1 C8 C9 O1 -16.9(11) . . . . ?
C7 C8 C9 O1 168.7(7) . . . . ?
N1 C8 C9 N4 161.5(6) . . . . ?
C7 C8 C9 N4 -12.9(11) . . . . ?
C9 N4 C10 C15 -60.2(9) . . . . ?
C9 N4 C10 C11 123.0(7) . . . . ?
C15 C10 C11 C12 4.0(9) . . . . ?
N4 C10 C11 C12 -179.2(5) . . . . ?
C15 C10 C11 C17 -175.9(6) . . . . ?
N4 C10 C11 C17 0.9(9) . . . . ?
C10 C11 C12 C13 -0.7(9) . . . . ?
C17 C11 C12 C13 179.2(6) . . . . ?
C11 C12 C13 C14 -1.2(9) . . . . ?
C11 C12 C13 Cl2 178.2(4) . . . . ?
C12 C13 C14 C15 -0.3(10) . . . . ?
Cl2 C13 C14 C15 -179.7(5) . . . . ?
C13 C14 C15 C10 3.5(10) . . . . ?
C13 C14 C15 C16 -174.5(6) . . . . ?
C11 C10 C15 C14 -5.3(9) . . . . ?
N4 C10 C15 C14 177.9(6) . . . . ?
C11 C10 C15 C16 172.6(6) . . . . ?
N4 C10 C15 C16 -4.1(9) . . . . ?
C18 N5 C17 O2 0.9(7) . . . . ?
C18 N5 C17 C11 179.5(6) . . . . ?
N6 O2 C17 N5 -0.1(7) . . . . ?
N6 O2 C17 C11 -178.9(5) . . . . ?
C10 C11 C17 N5 5.0(10) . . . . ?
C12 C11 C17 N5 -174.9(6) . . . . ?
C10 C11 C17 O2 -176.5(6) . . . . ?
C12 C11 C17 O2 3.7(8) . . . . ?
O2 N6 C18 N5 1.3(8) . . . . ?
O2 N6 C18 C19 -178.8(6) . . . . ?
C17 N5 C18 N6 -1.4(8) . . . . ?
C17 N5 C18 C19 178.7(6) . . . . ?
N6 C18 C19 C24 5.2(10) . . . . ?
N5 C18 C19 C24 -174.9(6) . . . . ?
N6 C18 C19 C20 -175.3(7) . . . . ?
N5 C18 C19 C20 4.7(10) . . . . ?
C24 C19 C20 C21 0.5(11) . . . . ?
C18 C19 C20 C21 -179.0(6) . . . . ?
C19 C20 C21 C22 -0.2(11) . . . . ?
C20 C21 C22 C23 0.0(11) . . . . ?
C20 C21 C22 Br2 -179.7(5) . . . . ?
C21 C22 C23 C24 -0.1(11) . . . . ?
Br2 C22 C23 C24 179.6(5) . . . . ?
C20 C19 C24 C23 -0.6(11) . . . . ?
C18 C19 C24 C23 178.9(6) . . . . ?
C22 C23 C24 C19 0.4(11) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.118
_refine_diff_density_min         -0.875
_refine_diff_density_rms         0.107