 
data_161125f 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C49 H14 Br Cl2 F20 N5 O' 
_chemical_formula_weight          1219.46 
 
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' 
 'F'  'F'   0.0171   0.0103 
 '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                    12.6210(11) 
_cell_length_b                    14.2349(12) 
_cell_length_c                    14.4631(13) 
_cell_angle_alpha                 79.920(2) 
_cell_angle_beta                  65.9060(10) 
_cell_angle_gamma                 84.354(3) 
_cell_volume                      2334.4(4) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     298(2) 
_cell_measurement_reflns_used     3021 
_cell_measurement_theta_min       2.285 
_cell_measurement_theta_max       20.823 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.41 
_exptl_crystal_size_mid           0.40 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       1.735 
_exptl_crystal_density_diffrn     1.735 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1200 
_exptl_absorpt_coefficient_mu     1.121 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.6564 
_exptl_absorpt_correction_T_max   0.8068 
_exptl_absorpt_process_details    sadabs 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       298(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   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             11933 
_diffrn_reflns_av_R_equivalents   0.0904 
_diffrn_reflns_av_sigmaI/netI     0.1198 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        15 
_diffrn_reflns_limit_k_min        -16 
_diffrn_reflns_limit_k_max        16 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        17 
_diffrn_reflns_theta_min          2.28 
_diffrn_reflns_theta_max          25.02 
_reflns_number_total              8090 
_reflns_number_gt                 3908 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SHELXTL' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.1562P)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     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          8090 
_refine_ls_number_parameters      731 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1688 
_refine_ls_R_factor_gt            0.1003 
_refine_ls_wR_factor_ref          0.2913 
_refine_ls_wR_factor_gt           0.2568 
_refine_ls_goodness_of_fit_ref    1.033 
_refine_ls_restrained_S_all       1.033 
_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 
Br1 Br 0.47504(9) 0.51285(5) 0.34044(8) 0.0853(4) Uani 1 1 d . . . 
Cl1 Cl 0.758(4) 0.331(3) 0.045(3) 0.370(18) Uani 0.52(4) 1 d P A 1 
Cl2 Cl 0.935(3) 0.4148(18) 0.064(2) 0.299(17) Uani 0.52(4) 1 d P A 1 
Cl1' Cl 0.691(4) 0.383(3) 0.084(3) 0.352(18) Uani 0.48(4) 1 d P A 2 
Cl2' Cl 0.875(5) 0.493(3) -0.041(4) 0.37(2) Uani 0.48(4) 1 d P A 2 
F1 F 0.6972(5) 0.1261(5) 0.0586(4) 0.111(2) Uani 1 1 d . . . 
F2 F 0.7843(6) 0.0228(6) -0.0963(5) 0.136(3) Uani 1 1 d . . . 
F3 F 0.9278(5) -0.1306(5) -0.0863(5) 0.133(3) Uani 1 1 d . . . 
F4 F 0.9896(5) -0.1739(4) 0.0727(5) 0.116(2) Uani 1 1 d . . . 
F5 F 0.9023(5) -0.0696(4) 0.2278(4) 0.0995(17) Uani 1 1 d . . . 
F6 F 0.8205(4) 0.0358(3) 0.4847(4) 0.0903(15) Uani 1 1 d . . . 
F7 F 1.0411(5) -0.0112(5) 0.3745(5) 0.116(2) Uani 1 1 d . . . 
F8 F 1.1889(4) 0.1222(5) 0.2355(5) 0.121(2) Uani 1 1 d . . . 
F9 F 1.1084(5) 0.3017(5) 0.2047(5) 0.137(2) Uani 1 1 d . . . 
F10 F 0.8864(5) 0.3518(4) 0.3132(4) 0.0978(16) Uani 1 1 d . . . 
F11 F 0.4283(5) 0.0750(4) 0.9504(4) 0.0923(15) Uani 1 1 d . . . 
F12 F 0.4230(5) 0.0655(4) 1.1410(4) 0.1009(17) Uani 1 1 d . . . 
F13 F 0.4394(5) 0.2255(5) 1.2078(4) 0.116(2) Uani 1 1 d . . . 
F14 F 0.4595(7) 0.3959(5) 1.0857(5) 0.147(3) Uani 1 1 d . . . 
F15 F 0.4708(6) 0.4052(4) 0.8952(4) 0.119(2) Uani 1 1 d . . . 
F16 F -0.0611(5) 0.2403(4) 0.7675(6) 0.118(2) Uani 1 1 d . . . 
F17 F -0.2462(5) 0.3560(6) 0.7899(7) 0.162(3) Uani 1 1 d . . . 
F18 F -0.2171(6) 0.5416(5) 0.6874(6) 0.143(3) Uani 1 1 d . . . 
F19 F 0.0007(6) 0.6045(4) 0.5663(6) 0.124(2) Uani 1 1 d . . . 
F20 F 0.1836(5) 0.4885(4) 0.5511(5) 0.0971(16) Uani 1 1 d . . . 
N4 N 0.4499(4) 0.1054(3) 0.4137(4) 0.0427(13) Uani 1 1 d . . . 
N5 N 0.5190(5) 0.3154(4) 0.3477(4) 0.0510(14) Uani 1 1 d . . . 
H5 H 0.4713 0.3119 0.3197 0.061 Uiso 1 1 calc R . . 
N1 N 0.5696(5) 0.2319(4) 0.6320(4) 0.0488(14) Uani 1 1 d . . . 
H1 H 0.5165 0.2509 0.6095 0.059 Uiso 1 1 calc R . . 
N2 N 0.3323(5) 0.2634(4) 0.7116(4) 0.0520(15) Uani 1 1 d . . . 
N3 N 0.3271(5) 0.1983(4) 0.5445(4) 0.0489(14) Uani 1 1 d . . . 
H3 H 0.3721 0.1938 0.5767 0.059 Uiso 1 1 calc R . . 
O1 O 0.8129(5) 0.1534(5) 0.2302(5) 0.094(2) Uani 1 1 d . . . 
C27 C 0.4565(6) 0.0191(5) 0.3824(6) 0.0539(18) Uani 1 1 d . . . 
H27 H 0.3938 -0.0202 0.4032 0.065 Uiso 1 1 calc R . . 
C28 C 0.5642(6) -0.0020(5) 0.3184(6) 0.0571(18) Uani 1 1 d . . . 
H28 H 0.5895 -0.0566 0.2873 0.068 Uiso 1 1 calc R . . 
C29 C 0.6332(6) 0.0772(5) 0.3073(5) 0.0519(17) Uani 1 1 d . . . 
C37 C 0.5618(6) 0.1431(4) 0.3660(5) 0.0466(16) Uani 1 1 d . . . 
C38 C 0.5826(6) 0.2400(5) 0.3755(5) 0.0490(17) Uani 1 1 d . . . 
C39 C 0.6447(6) 0.2747(5) 0.4186(5) 0.0467(16) Uani 1 1 d . . . 
C40 C 0.6224(6) 0.3738(5) 0.4133(5) 0.0514(17) Uani 1 1 d . . . 
H40 H 0.6558 0.4165 0.4347 0.062 Uiso 1 1 calc R . . 
C41 C 0.5437(6) 0.3954(5) 0.3715(5) 0.0503(17) Uani 1 1 d . . . 
C42 C 0.7212(6) 0.2236(5) 0.4688(6) 0.0506(17) Uani 1 1 d . . . 
C1 C 0.6822(6) 0.2099(5) 0.5707(6) 0.0497(17) Uani 1 1 d . . . 
C2 C 0.7376(7) 0.1781(5) 0.6400(6) 0.0595(19) Uani 1 1 d . . . 
H2 H 0.8145 0.1563 0.6209 0.071 Uiso 1 1 calc R . . 
C3 C 0.6636(6) 0.1841(5) 0.7354(6) 0.0588(19) Uani 1 1 d . . . 
H3A H 0.6802 0.1684 0.7933 0.071 Uiso 1 1 calc R . . 
C4 C 0.5515(6) 0.2198(5) 0.7341(5) 0.0511(17) Uani 1 1 d . . . 
C5 C 0.4512(6) 0.2432(5) 0.8125(5) 0.0536(18) Uani 1 1 d . . . 
C12 C 0.3469(6) 0.2757(5) 0.7964(6) 0.0562(19) Uani 1 1 d . . . 
C13 C 0.2482(6) 0.3277(6) 0.8606(6) 0.065(2) Uani 1 1 d . . . 
H13 H 0.2381 0.3447 0.9230 0.078 Uiso 1 1 calc R . . 
C14 C 0.1751(7) 0.3469(6) 0.8160(6) 0.065(2) Uani 1 1 d . . . 
H14 H 0.1046 0.3805 0.8407 0.078 Uiso 1 1 calc R . . 
C15 C 0.2234(6) 0.3066(5) 0.7217(6) 0.0573(19) Uani 1 1 d . . . 
C16 C 0.1746(6) 0.3021(5) 0.6537(6) 0.0563(19) Uani 1 1 d . . . 
C23 C 0.2220(6) 0.2503(5) 0.5692(6) 0.0493(17) Uani 1 1 d . . . 
C24 C 0.1773(6) 0.2349(5) 0.5011(6) 0.0564(19) Uani 1 1 d . . . 
H24 H 0.1062 0.2587 0.5005 0.068 Uiso 1 1 calc R . . 
C25 C 0.2571(6) 0.1772(5) 0.4323(6) 0.0582(19) Uani 1 1 d . . . 
H25 H 0.2497 0.1574 0.3773 0.070 Uiso 1 1 calc R . . 
C26 C 0.3468(6) 0.1561(4) 0.4619(5) 0.0465(16) Uani 1 1 d . . . 
C30 C 0.7535(6) 0.0930(6) 0.2315(6) 0.0587(19) Uani 1 1 d . . . 
C31 C 0.7964(6) 0.0299(6) 0.1483(6) 0.062(2) Uani 1 1 d . . . 
C32 C 0.7688(7) 0.0516(6) 0.0634(7) 0.072(2) Uani 1 1 d . . . 
C33 C 0.8105(8) -0.0014(8) -0.0134(7) 0.084(3) Uani 1 1 d . . . 
C34 C 0.8833(9) -0.0793(8) -0.0091(8) 0.087(3) Uani 1 1 d . . . 
C35 C 0.9145(8) -0.1022(7) 0.0707(8) 0.083(3) Uani 1 1 d . . . 
C36 C 0.8692(7) -0.0473(6) 0.1500(6) 0.068(2) Uani 1 1 d . . . 
C43 C 0.8449(6) 0.1971(6) 0.4059(6) 0.0576(19) Uani 1 1 d . . . 
C44 C 0.8889(7) 0.1047(6) 0.4178(6) 0.066(2) Uani 1 1 d . . . 
C45 C 1.0011(8) 0.0755(7) 0.3650(7) 0.076(2) Uani 1 1 d . . . 
C46 C 1.0718(8) 0.1432(9) 0.2933(8) 0.083(3) Uani 1 1 d . . . 
C47 C 1.0356(8) 0.2336(8) 0.2772(7) 0.087(3) Uani 1 1 d . . . 
C48 C 0.9213(7) 0.2621(7) 0.3309(7) 0.069(2) Uani 1 1 d . . . 
C6 C 0.4485(6) 0.2388(6) 0.9171(6) 0.0564(18) Uani 1 1 d . . . 
C11 C 0.4376(6) 0.1550(6) 0.9816(6) 0.0613(19) Uani 1 1 d . . . 
C10 C 0.4337(7) 0.1500(6) 1.0807(6) 0.067(2) Uani 1 1 d . . . 
C9 C 0.4441(8) 0.2307(8) 1.1104(7) 0.076(2) Uani 1 1 d . . . 
C8 C 0.4524(9) 0.3151(7) 1.0518(7) 0.087(3) Uani 1 1 d . . . 
C7 C 0.4574(8) 0.3190(7) 0.9544(7) 0.077(2) Uani 1 1 d . . . 
C17 C 0.0680(7) 0.3620(6) 0.6621(7) 0.065(2) Uani 1 1 d . . . 
C22 C -0.0450(8) 0.3302(7) 0.7208(8) 0.082(3) Uani 1 1 d . . . 
C21 C -0.1371(8) 0.3923(8) 0.7279(9) 0.095(3) Uani 1 1 d . . . 
C20 C -0.1237(9) 0.4819(8) 0.6776(9) 0.088(3) Uani 1 1 d . . . 
C19 C -0.0178(9) 0.5125(7) 0.6212(8) 0.083(3) Uani 1 1 d . . . 
C18 C 0.0754(8) 0.4517(6) 0.6137(7) 0.071(2) Uani 1 1 d . . . 
C49 C 0.849(16) 0.425(13) -0.005(13) 0.35(9) Uani 0.52(4) 1 d P A 1 
H49A H 0.8048 0.4846 0.0007 0.421 Uiso 0.52(4) 1 calc PR A 1 
H49B H 0.8967 0.4222 -0.0771 0.421 Uiso 0.52(4) 1 calc PR A 1 
C49' C 0.815(13) 0.420(9) 0.082(10) 0.33(6) Uani 0.48(4) 1 d P A 2 
H49C H 0.8667 0.3666 0.0887 0.390 Uiso 0.48(4) 1 calc PR A 2 
H49D H 0.7986 0.4572 0.1372 0.390 Uiso 0.48(4) 1 calc PR A 2 
 
 
_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 C41 1.876(7) . ? 
Cl1 C49 1.70(16) . ? 
Cl2 C49 1.7(2) . ? 
Cl1' C49' 1.69(17) . ? 
Cl2' C49' 1.80(15) . ? 
F1 C32 1.336(9) . ? 
F2 C33 1.349(10) . ? 
F3 C34 1.338(9) . ? 
F4 C35 1.328(10) . ? 
F5 C36 1.333(9) . ? 
F6 C44 1.340(9) . ? 
F7 C45 1.292(10) . ? 
F8 C46 1.402(10) . ? 
F9 C47 1.384(11) . ? 
F10 C48 1.325(10) . ? 
F11 C11 1.328(8) . ? 
F12 C10 1.339(9) . ? 
F13 C9 1.374(9) . ? 
F14 C8 1.351(10) . ? 
F15 C7 1.349(10) . ? 
F16 C22 1.331(11) . ? 
F17 C21 1.392(12) . ? 
F18 C20 1.357(10) . ? 
F19 C19 1.395(11) . ? 
F20 C18 1.387(10) . ? 
N4 C27 1.366(8) . ? 
N4 C26 1.396(8) . ? 
N4 C37 1.407(8) . ? 
N5 C41 1.344(8) . ? 
N5 C38 1.379(8) . ? 
N5 H5 0.8600 . ? 
N1 C1 1.373(8) . ? 
N1 C4 1.381(8) . ? 
N1 H1 0.8600 . ? 
N2 C12 1.355(8) . ? 
N2 C15 1.410(8) . ? 
N3 C26 1.354(8) . ? 
N3 C23 1.396(8) . ? 
N3 H3 0.8600 . ? 
O1 C30 1.188(8) . ? 
C27 C28 1.336(10) . ? 
C27 H27 0.9300 . ? 
C28 C29 1.438(9) . ? 
C28 H28 0.9300 . ? 
C29 C37 1.378(9) . ? 
C29 C30 1.476(10) . ? 
C37 C38 1.469(9) . ? 
C38 C39 1.352(9) . ? 
C39 C40 1.407(9) . ? 
C39 C42 1.496(9) . ? 
C40 C41 1.346(9) . ? 
C40 H40 0.9300 . ? 
C42 C1 1.334(10) . ? 
C42 C43 1.501(10) . ? 
C1 C2 1.432(9) . ? 
C2 C3 1.326(10) . ? 
C2 H2 0.9300 . ? 
C3 C4 1.462(9) . ? 
C3 H3A 0.9300 . ? 
C4 C5 1.370(10) . ? 
C5 C12 1.447(9) . ? 
C5 C6 1.489(10) . ? 
C12 C13 1.441(10) . ? 
C13 C14 1.310(10) . ? 
C13 H13 0.9300 . ? 
C14 C15 1.445(10) . ? 
C14 H14 0.9300 . ? 
C15 C16 1.369(9) . ? 
C16 C23 1.424(9) . ? 
C16 C17 1.492(10) . ? 
C23 C24 1.375(9) . ? 
C24 C25 1.408(10) . ? 
C24 H24 0.9300 . ? 
C25 C26 1.355(9) . ? 
C25 H25 0.9300 . ? 
C30 C31 1.516(10) . ? 
C31 C36 1.364(11) . ? 
C31 C32 1.386(11) . ? 
C32 C33 1.348(12) . ? 
C33 C34 1.379(13) . ? 
C34 C35 1.343(14) . ? 
C35 C36 1.394(11) . ? 
C43 C44 1.387(11) . ? 
C43 C48 1.391(11) . ? 
C44 C45 1.368(11) . ? 
C45 C46 1.366(13) . ? 
C46 C47 1.336(13) . ? 
C47 C48 1.389(12) . ? 
C6 C11 1.361(10) . ? 
C6 C7 1.377(11) . ? 
C11 C10 1.403(11) . ? 
C10 C9 1.331(11) . ? 
C9 C8 1.330(12) . ? 
C8 C7 1.377(12) . ? 
C17 C18 1.337(11) . ? 
C17 C22 1.401(12) . ? 
C22 C21 1.370(12) . ? 
C21 C20 1.343(14) . ? 
C20 C19 1.320(14) . ? 
C19 C18 1.368(11) . ? 
C49 H49A 0.9700 . ? 
C49 H49B 0.9700 . ? 
C49' H49C 0.9700 . ? 
C49' H49D 0.9700 . ? 
 
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 
C27 N4 C26 124.8(5) . . ? 
C27 N4 C37 107.4(5) . . ? 
C26 N4 C37 126.0(5) . . ? 
C41 N5 C38 108.8(6) . . ? 
C41 N5 H5 125.6 . . ? 
C38 N5 H5 125.6 . . ? 
C1 N1 C4 112.0(5) . . ? 
C1 N1 H1 124.0 . . ? 
C4 N1 H1 124.0 . . ? 
C12 N2 C15 105.7(6) . . ? 
C26 N3 C23 108.9(5) . . ? 
C26 N3 H3 125.5 . . ? 
C23 N3 H3 125.5 . . ? 
C28 C27 N4 111.7(6) . . ? 
C28 C27 H27 124.2 . . ? 
N4 C27 H27 124.2 . . ? 
C27 C28 C29 105.9(6) . . ? 
C27 C28 H28 127.0 . . ? 
C29 C28 H28 127.0 . . ? 
C37 C29 C28 108.2(6) . . ? 
C37 C29 C30 125.6(6) . . ? 
C28 C29 C30 125.3(6) . . ? 
C29 C37 N4 106.9(5) . . ? 
C29 C37 C38 131.6(6) . . ? 
N4 C37 C38 121.2(5) . . ? 
C39 C38 N5 107.4(6) . . ? 
C39 C38 C37 133.4(6) . . ? 
N5 C38 C37 118.7(5) . . ? 
C38 C39 C40 107.6(6) . . ? 
C38 C39 C42 130.1(6) . . ? 
C40 C39 C42 122.2(6) . . ? 
C41 C40 C39 107.2(6) . . ? 
C41 C40 H40 126.4 . . ? 
C39 C40 H40 126.4 . . ? 
N5 C41 C40 109.0(6) . . ? 
N5 C41 Br1 120.1(5) . . ? 
C40 C41 Br1 130.8(5) . . ? 
C1 C42 C39 119.3(6) . . ? 
C1 C42 C43 119.7(6) . . ? 
C39 C42 C43 120.7(6) . . ? 
C42 C1 N1 122.2(6) . . ? 
C42 C1 C2 132.8(7) . . ? 
N1 C1 C2 104.9(6) . . ? 
C3 C2 C1 110.2(6) . . ? 
C3 C2 H2 124.9 . . ? 
C1 C2 H2 124.9 . . ? 
C2 C3 C4 108.5(6) . . ? 
C2 C3 H3A 125.8 . . ? 
C4 C3 H3A 125.8 . . ? 
C5 C4 N1 125.7(6) . . ? 
C5 C4 C3 129.9(6) . . ? 
N1 C4 C3 104.3(6) . . ? 
C4 C5 C12 121.8(6) . . ? 
C4 C5 C6 120.1(6) . . ? 
C12 C5 C6 118.1(6) . . ? 
N2 C12 C13 109.9(6) . . ? 
N2 C12 C5 122.2(6) . . ? 
C13 C12 C5 127.8(6) . . ? 
C14 C13 C12 108.2(6) . . ? 
C14 C13 H13 125.9 . . ? 
C12 C13 H13 125.9 . . ? 
C13 C14 C15 107.9(6) . . ? 
C13 C14 H14 126.0 . . ? 
C15 C14 H14 126.0 . . ? 
C16 C15 N2 122.6(6) . . ? 
C16 C15 C14 129.1(7) . . ? 
N2 C15 C14 108.2(6) . . ? 
C15 C16 C23 125.4(6) . . ? 
C15 C16 C17 118.4(6) . . ? 
C23 C16 C17 116.0(6) . . ? 
C24 C23 N3 106.1(6) . . ? 
C24 C23 C16 130.5(6) . . ? 
N3 C23 C16 123.3(5) . . ? 
C23 C24 C25 108.7(6) . . ? 
C23 C24 H24 125.7 . . ? 
C25 C24 H24 125.7 . . ? 
C26 C25 C24 106.7(6) . . ? 
C26 C25 H25 126.7 . . ? 
C24 C25 H25 126.7 . . ? 
N3 C26 C25 109.6(6) . . ? 
N3 C26 N4 122.4(5) . . ? 
C25 C26 N4 127.8(6) . . ? 
O1 C30 C29 124.1(6) . . ? 
O1 C30 C31 120.5(7) . . ? 
C29 C30 C31 115.2(6) . . ? 
C36 C31 C32 116.7(7) . . ? 
C36 C31 C30 122.1(7) . . ? 
C32 C31 C30 121.1(7) . . ? 
F1 C32 C33 119.2(8) . . ? 
F1 C32 C31 118.9(7) . . ? 
C33 C32 C31 121.8(9) . . ? 
C32 C33 F2 120.5(10) . . ? 
C32 C33 C34 120.0(9) . . ? 
F2 C33 C34 119.5(9) . . ? 
F3 C34 C35 119.2(10) . . ? 
F3 C34 C33 120.4(10) . . ? 
C35 C34 C33 120.4(8) . . ? 
F4 C35 C34 120.8(9) . . ? 
F4 C35 C36 120.5(10) . . ? 
C34 C35 C36 118.7(9) . . ? 
F5 C36 C31 119.4(7) . . ? 
F5 C36 C35 118.2(8) . . ? 
C31 C36 C35 122.3(9) . . ? 
C44 C43 C48 115.9(7) . . ? 
C44 C43 C42 121.5(8) . . ? 
C48 C43 C42 122.6(7) . . ? 
F6 C44 C45 114.7(8) . . ? 
F6 C44 C43 120.4(7) . . ? 
C45 C44 C43 124.9(9) . . ? 
F7 C45 C46 119.1(8) . . ? 
F7 C45 C44 124.7(10) . . ? 
C46 C45 C44 116.0(9) . . ? 
C47 C46 C45 122.5(9) . . ? 
C47 C46 F8 116.2(11) . . ? 
C45 C46 F8 121.3(10) . . ? 
C46 C47 F9 121.9(10) . . ? 
C46 C47 C48 120.8(10) . . ? 
F9 C47 C48 117.3(10) . . ? 
F10 C48 C47 120.1(9) . . ? 
F10 C48 C43 120.2(7) . . ? 
C47 C48 C43 119.7(9) . . ? 
C11 C6 C7 115.8(7) . . ? 
C11 C6 C5 121.9(7) . . ? 
C7 C6 C5 122.3(7) . . ? 
F11 C11 C6 118.8(7) . . ? 
F11 C11 C10 118.6(7) . . ? 
C6 C11 C10 122.5(7) . . ? 
C9 C10 F12 122.1(8) . . ? 
C9 C10 C11 117.8(8) . . ? 
F12 C10 C11 120.0(8) . . ? 
C8 C9 C10 122.5(8) . . ? 
C8 C9 F13 119.8(9) . . ? 
C10 C9 F13 117.6(8) . . ? 
C9 C8 F14 120.8(8) . . ? 
C9 C8 C7 119.1(8) . . ? 
F14 C8 C7 120.1(9) . . ? 
F15 C7 C8 117.7(8) . . ? 
F15 C7 C6 120.1(7) . . ? 
C8 C7 C6 122.2(8) . . ? 
C18 C17 C22 115.4(8) . . ? 
C18 C17 C16 121.0(8) . . ? 
C22 C17 C16 123.6(8) . . ? 
F16 C22 C21 121.2(9) . . ? 
F16 C22 C17 119.7(7) . . ? 
C21 C22 C17 119.1(9) . . ? 
C20 C21 C22 122.5(10) . . ? 
C20 C21 F17 122.0(9) . . ? 
C22 C21 F17 115.5(10) . . ? 
C19 C20 C21 119.0(9) . . ? 
C19 C20 F18 120.3(10) . . ? 
C21 C20 F18 120.7(10) . . ? 
C20 C19 C18 119.4(10) . . ? 
C20 C19 F19 121.2(9) . . ? 
C18 C19 F19 119.4(10) . . ? 
C17 C18 C19 124.6(10) . . ? 
C17 C18 F20 119.6(7) . . ? 
C19 C18 F20 115.8(8) . . ? 
Cl1 C49 Cl2 107(10) . . ? 
Cl1 C49 H49A 110.4 . . ? 
Cl2 C49 H49A 110.4 . . ? 
Cl1 C49 H49B 110.4 . . ? 
Cl2 C49 H49B 110.4 . . ? 
H49A C49 H49B 108.6 . . ? 
Cl1' C49' Cl2' 102(10) . . ? 
Cl1' C49' H49C 111.3 . . ? 
Cl2' C49' H49C 111.3 . . ? 
Cl1' C49' H49D 111.3 . . ? 
Cl2' C49' H49D 111.3 . . ? 
H49C C49' H49D 109.2 . . ? 
 
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 
C26 N4 C27 C28 165.4(6) . . . . ? 
C37 N4 C27 C28 0.1(8) . . . . ? 
N4 C27 C28 C29 0.1(8) . . . . ? 
C27 C28 C29 C37 -0.3(8) . . . . ? 
C27 C28 C29 C30 -169.8(7) . . . . ? 
C28 C29 C37 N4 0.4(7) . . . . ? 
C30 C29 C37 N4 169.8(6) . . . . ? 
C28 C29 C37 C38 -173.1(7) . . . . ? 
C30 C29 C37 C38 -3.7(11) . . . . ? 
C27 N4 C37 C29 -0.3(7) . . . . ? 
C26 N4 C37 C29 -165.4(6) . . . . ? 
C27 N4 C37 C38 174.0(6) . . . . ? 
C26 N4 C37 C38 8.9(9) . . . . ? 
C41 N5 C38 C39 1.3(8) . . . . ? 
C41 N5 C38 C37 174.2(6) . . . . ? 
C29 C37 C38 C39 -71.7(11) . . . . ? 
N4 C37 C38 C39 115.6(9) . . . . ? 
C29 C37 C38 N5 117.5(8) . . . . ? 
N4 C37 C38 N5 -55.2(9) . . . . ? 
N5 C38 C39 C40 -2.4(8) . . . . ? 
C37 C38 C39 C40 -173.9(7) . . . . ? 
N5 C38 C39 C42 175.1(6) . . . . ? 
C37 C38 C39 C42 3.6(13) . . . . ? 
C38 C39 C40 C41 2.7(8) . . . . ? 
C42 C39 C40 C41 -175.0(6) . . . . ? 
C38 N5 C41 C40 0.5(8) . . . . ? 
C38 N5 C41 Br1 178.3(5) . . . . ? 
C39 C40 C41 N5 -1.9(7) . . . . ? 
C39 C40 C41 Br1 -179.4(5) . . . . ? 
C38 C39 C42 C1 -103.5(9) . . . . ? 
C40 C39 C42 C1 73.7(9) . . . . ? 
C38 C39 C42 C43 82.9(9) . . . . ? 
C40 C39 C42 C43 -100.0(8) . . . . ? 
C39 C42 C1 N1 7.0(10) . . . . ? 
C43 C42 C1 N1 -179.2(6) . . . . ? 
C39 C42 C1 C2 -168.9(7) . . . . ? 
C43 C42 C1 C2 4.8(12) . . . . ? 
C4 N1 C1 C42 -174.5(6) . . . . ? 
C4 N1 C1 C2 2.4(7) . . . . ? 
C42 C1 C2 C3 174.4(8) . . . . ? 
N1 C1 C2 C3 -2.1(8) . . . . ? 
C1 C2 C3 C4 1.0(9) . . . . ? 
C1 N1 C4 C5 174.5(7) . . . . ? 
C1 N1 C4 C3 -1.9(7) . . . . ? 
C2 C3 C4 C5 -175.6(7) . . . . ? 
C2 C3 C4 N1 0.5(8) . . . . ? 
N1 C4 C5 C12 6.1(11) . . . . ? 
C3 C4 C5 C12 -178.5(7) . . . . ? 
N1 C4 C5 C6 -171.7(6) . . . . ? 
C3 C4 C5 C6 3.7(12) . . . . ? 
C15 N2 C12 C13 -0.7(8) . . . . ? 
C15 N2 C12 C5 -178.1(7) . . . . ? 
C4 C5 C12 N2 16.4(11) . . . . ? 
C6 C5 C12 N2 -165.8(7) . . . . ? 
C4 C5 C12 C13 -160.6(8) . . . . ? 
C6 C5 C12 C13 17.3(11) . . . . ? 
N2 C12 C13 C14 -0.1(9) . . . . ? 
C5 C12 C13 C14 177.1(8) . . . . ? 
C12 C13 C14 C15 0.8(9) . . . . ? 
C12 N2 C15 C16 -174.9(7) . . . . ? 
C12 N2 C15 C14 1.1(8) . . . . ? 
C13 C14 C15 C16 174.5(8) . . . . ? 
C13 C14 C15 N2 -1.3(9) . . . . ? 
N2 C15 C16 C23 3.8(12) . . . . ? 
C14 C15 C16 C23 -171.4(8) . . . . ? 
N2 C15 C16 C17 -171.0(7) . . . . ? 
C14 C15 C16 C17 13.8(12) . . . . ? 
C26 N3 C23 C24 2.2(8) . . . . ? 
C26 N3 C23 C16 178.9(7) . . . . ? 
C15 C16 C23 C24 174.6(8) . . . . ? 
C17 C16 C23 C24 -10.5(12) . . . . ? 
C15 C16 C23 N3 -1.2(12) . . . . ? 
C17 C16 C23 N3 173.7(6) . . . . ? 
N3 C23 C24 C25 -2.5(8) . . . . ? 
C16 C23 C24 C25 -178.8(8) . . . . ? 
C23 C24 C25 C26 1.9(9) . . . . ? 
C23 N3 C26 C25 -1.1(8) . . . . ? 
C23 N3 C26 N4 174.6(6) . . . . ? 
C24 C25 C26 N3 -0.5(8) . . . . ? 
C24 C25 C26 N4 -175.9(7) . . . . ? 
C27 N4 C26 N3 135.7(7) . . . . ? 
C37 N4 C26 N3 -61.8(9) . . . . ? 
C27 N4 C26 C25 -49.5(10) . . . . ? 
C37 N4 C26 C25 113.0(8) . . . . ? 
C37 C29 C30 O1 20.2(12) . . . . ? 
C28 C29 C30 O1 -172.1(8) . . . . ? 
C37 C29 C30 C31 -156.0(7) . . . . ? 
C28 C29 C30 C31 11.6(11) . . . . ? 
O1 C30 C31 C36 81.0(11) . . . . ? 
C29 C30 C31 C36 -102.6(9) . . . . ? 
O1 C30 C31 C32 -95.0(10) . . . . ? 
C29 C30 C31 C32 81.4(10) . . . . ? 
C36 C31 C32 F1 179.5(7) . . . . ? 
C30 C31 C32 F1 -4.3(13) . . . . ? 
C36 C31 C32 C33 0.8(13) . . . . ? 
C30 C31 C32 C33 177.1(8) . . . . ? 
F1 C32 C33 F2 2.9(14) . . . . ? 
C31 C32 C33 F2 -178.4(8) . . . . ? 
F1 C32 C33 C34 -179.1(9) . . . . ? 
C31 C32 C33 C34 -0.5(15) . . . . ? 
C32 C33 C34 F3 -178.0(9) . . . . ? 
F2 C33 C34 F3 0.0(15) . . . . ? 
C32 C33 C34 C35 -0.9(16) . . . . ? 
F2 C33 C34 C35 177.1(9) . . . . ? 
F3 C34 C35 F4 0.8(15) . . . . ? 
C33 C34 C35 F4 -176.3(9) . . . . ? 
F3 C34 C35 C36 178.9(8) . . . . ? 
C33 C34 C35 C36 1.8(15) . . . . ? 
C32 C31 C36 F5 177.5(8) . . . . ? 
C30 C31 C36 F5 1.3(12) . . . . ? 
C32 C31 C36 C35 0.2(13) . . . . ? 
C30 C31 C36 C35 -176.0(8) . . . . ? 
F4 C35 C36 F5 -0.7(13) . . . . ? 
C34 C35 C36 F5 -178.8(9) . . . . ? 
F4 C35 C36 C31 176.7(8) . . . . ? 
C34 C35 C36 C31 -1.5(14) . . . . ? 
C1 C42 C43 C44 58.0(9) . . . . ? 
C39 C42 C43 C44 -128.3(7) . . . . ? 
C1 C42 C43 C48 -123.4(8) . . . . ? 
C39 C42 C43 C48 50.2(9) . . . . ? 
C48 C43 C44 F6 -176.9(7) . . . . ? 
C42 C43 C44 F6 1.7(11) . . . . ? 
C48 C43 C44 C45 2.8(12) . . . . ? 
C42 C43 C44 C45 -178.5(7) . . . . ? 
F6 C44 C45 F7 1.6(12) . . . . ? 
C43 C44 C45 F7 -178.2(8) . . . . ? 
F6 C44 C45 C46 177.5(7) . . . . ? 
C43 C44 C45 C46 -2.2(12) . . . . ? 
F7 C45 C46 C47 178.2(8) . . . . ? 
C44 C45 C46 C47 2.0(14) . . . . ? 
F7 C45 C46 F8 -4.8(13) . . . . ? 
C44 C45 C46 F8 179.0(7) . . . . ? 
C45 C46 C47 F9 179.6(8) . . . . ? 
F8 C46 C47 F9 2.4(13) . . . . ? 
C45 C46 C47 C48 -2.5(15) . . . . ? 
F8 C46 C47 C48 -179.7(7) . . . . ? 
C46 C47 C48 F10 -179.2(8) . . . . ? 
F9 C47 C48 F10 -1.2(12) . . . . ? 
C46 C47 C48 C43 3.1(13) . . . . ? 
F9 C47 C48 C43 -179.0(7) . . . . ? 
C44 C43 C48 F10 179.2(7) . . . . ? 
C42 C43 C48 F10 0.5(11) . . . . ? 
C44 C43 C48 C47 -3.1(11) . . . . ? 
C42 C43 C48 C47 178.3(7) . . . . ? 
C4 C5 C6 C11 -79.8(10) . . . . ? 
C12 C5 C6 C11 102.3(9) . . . . ? 
C4 C5 C6 C7 99.9(9) . . . . ? 
C12 C5 C6 C7 -78.0(10) . . . . ? 
C7 C6 C11 F11 179.8(7) . . . . ? 
C5 C6 C11 F11 -0.5(11) . . . . ? 
C7 C6 C11 C10 1.0(12) . . . . ? 
C5 C6 C11 C10 -179.3(7) . . . . ? 
F11 C11 C10 C9 179.4(7) . . . . ? 
C6 C11 C10 C9 -1.7(12) . . . . ? 
F11 C11 C10 F12 1.2(11) . . . . ? 
C6 C11 C10 F12 -180.0(7) . . . . ? 
F12 C10 C9 C8 -178.6(9) . . . . ? 
C11 C10 C9 C8 3.2(14) . . . . ? 
F12 C10 C9 F13 -2.2(13) . . . . ? 
C11 C10 C9 F13 179.6(7) . . . . ? 
C10 C9 C8 F14 178.1(9) . . . . ? 
F13 C9 C8 F14 1.8(15) . . . . ? 
C10 C9 C8 C7 -3.9(16) . . . . ? 
F13 C9 C8 C7 179.8(8) . . . . ? 
C9 C8 C7 F15 -177.2(9) . . . . ? 
F14 C8 C7 F15 0.8(15) . . . . ? 
C9 C8 C7 C6 3.1(15) . . . . ? 
F14 C8 C7 C6 -178.8(9) . . . . ? 
C11 C6 C7 F15 178.7(8) . . . . ? 
C5 C6 C7 F15 -1.0(13) . . . . ? 
C11 C6 C7 C8 -1.7(13) . . . . ? 
C5 C6 C7 C8 178.6(8) . . . . ? 
C15 C16 C17 C18 87.9(10) . . . . ? 
C23 C16 C17 C18 -87.4(9) . . . . ? 
C15 C16 C17 C22 -91.3(9) . . . . ? 
C23 C16 C17 C22 93.5(10) . . . . ? 
C18 C17 C22 F16 176.6(8) . . . . ? 
C16 C17 C22 F16 -4.2(13) . . . . ? 
C18 C17 C22 C21 -2.6(13) . . . . ? 
C16 C17 C22 C21 176.6(8) . . . . ? 
F16 C22 C21 C20 -176.7(10) . . . . ? 
C17 C22 C21 C20 2.5(16) . . . . ? 
F16 C22 C21 F17 2.6(15) . . . . ? 
C17 C22 C21 F17 -178.3(8) . . . . ? 
C22 C21 C20 C19 -1.8(17) . . . . ? 
F17 C21 C20 C19 179.0(9) . . . . ? 
C22 C21 C20 F18 -179.4(9) . . . . ? 
F17 C21 C20 F18 1.4(16) . . . . ? 
C21 C20 C19 C18 1.3(15) . . . . ? 
F18 C20 C19 C18 178.9(8) . . . . ? 
C21 C20 C19 F19 179.0(9) . . . . ? 
F18 C20 C19 F19 -3.4(14) . . . . ? 
C22 C17 C18 C19 2.3(12) . . . . ? 
C16 C17 C18 C19 -176.9(7) . . . . ? 
C22 C17 C18 F20 -177.9(7) . . . . ? 
C16 C17 C18 F20 2.8(11) . . . . ? 
C20 C19 C18 C17 -1.7(14) . . . . ? 
F19 C19 C18 C17 -179.4(8) . . . . ? 
C20 C19 C18 F20 178.5(8) . . . . ? 
F19 C19 C18 F20 0.8(11) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.982 
_diffrn_reflns_theta_full              25.02 
_diffrn_measured_fraction_theta_full   0.982 
_refine_diff_density_max    0.717 
_refine_diff_density_min   -1.068 
_refine_diff_density_rms    0.121 


