data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H25 Br N2 O5' _chemical_formula_sum 'C22 H25 Br N2 O5' _chemical_formula_weight 477.35 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' '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' 'Br' 'Br' -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca2(1) _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 22.975(4) _cell_length_b 12.4694(16) _cell_length_c 7.5472(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2162.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 435 _cell_measurement_theta_min 3.22 _cell_measurement_theta_max 68.12 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 2.897 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.3903 _exptl_absorpt_correction_T_max 0.5312 _exptl_absorpt_process_details 'NUMABS by T.Higashi Jun 3, 2003' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54186 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku raxis Rapid IP Area Detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9769 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.1443 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 68.19 _reflns_number_total 3574 _reflns_number_gt 3298 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto Ver 2.30(Rigaku 1998)' _computing_cell_refinement 'Rapid Auto Ver 2.30(Rigaku 1998)' _computing_data_reduction 'Rapid Auto Ver 2.30(Rigaku 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (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^)+(0.0315P)^2^+1.2214P] 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 SHELXL _refine_ls_extinction_coef 0.00082(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.005(19) _refine_ls_number_reflns 3574 _refine_ls_number_parameters 286 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0826 _refine_ls_wR_factor_gt 0.0798 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.088 _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 0.712738(19) 0.57358(3) 0.85656(8) 0.05758(16) Uani 1 1 d . . . O1 O 0.50991(11) 0.32658(19) 0.4543(4) 0.0464(7) Uani 1 1 d . . . O2 O 0.47572(10) -0.20420(19) 0.5509(4) 0.0442(7) Uani 1 1 d . . . O3 O 0.56394(11) -0.2427(2) 0.4477(4) 0.0521(7) Uani 1 1 d . A . O4 O 0.71549(9) 0.03870(19) 0.9168(3) 0.0333(6) Uani 1 1 d . . . O5 O 0.63564(9) -0.03589(17) 1.0383(3) 0.0264(5) Uani 1 1 d . . . N1 N 0.61261(10) 0.11646(19) 0.4606(3) 0.0244(5) Uani 1 1 d . . . N2 N 0.55848(11) 0.16792(19) 0.5023(3) 0.0264(6) Uani 1 1 d . . . C1 C 0.51099(13) 0.1102(3) 0.5657(4) 0.0299(7) Uani 1 1 d . . . H1A H 0.4762 0.1506 0.5793 0.036 Uiso 1 1 calc R . . C2 C 0.50670(15) 0.0068(3) 0.6106(5) 0.0287(7) Uani 1 1 d . . . H2A H 0.4695 -0.0151 0.6516 0.034 Uiso 1 1 calc R . . C3 C 0.55115(13) -0.0783(2) 0.6058(4) 0.0269(7) Uani 1 1 d . . . C4 C 0.60557(13) -0.0689(2) 0.6715(4) 0.0229(6) Uani 1 1 d . . . C5 C 0.62352(13) 0.0368(2) 0.7565(4) 0.0226(6) Uani 1 1 d . . . H5A H 0.5878 0.0725 0.8041 0.027 Uiso 1 1 calc R . . C6 C 0.65168(12) 0.1123(2) 0.6192(4) 0.0234(6) Uani 1 1 d . . . H6A H 0.6887 0.0773 0.5800 0.028 Uiso 1 1 calc R . . C7 C 0.63592(13) 0.1861(2) 0.3165(4) 0.0299(8) Uani 1 1 d . . . H7A H 0.6257 0.1559 0.1992 0.036 Uiso 1 1 calc R . . H7B H 0.6788 0.1911 0.3252 0.036 Uiso 1 1 calc R . . C8 C 0.60848(13) 0.2967(2) 0.3393(5) 0.0323(7) Uani 1 1 d . . . H8A H 0.6338 0.3447 0.4099 0.039 Uiso 1 1 calc R . . H8B H 0.6004 0.3306 0.2233 0.039 Uiso 1 1 calc R . . C9 C 0.55318(15) 0.2713(3) 0.4365(4) 0.0328(7) Uani 1 1 d . . . C10 C 0.52668(14) -0.1814(3) 0.5359(5) 0.0319(7) Uani 1 1 d . . . C11 C 0.54200(19) -0.3484(3) 0.3922(8) 0.0677(15) Uani 1 1 d D . . H11A H 0.5122 -0.3391 0.3043 0.081 Uiso 0.474(11) 1 d PR A . H11B H 0.5247 -0.3828 0.4931 0.081 Uiso 0.474(11) 1 d PR . . H11C H 0.5574 -0.3688 0.2788 0.081 Uiso 0.526(11) 1 d PR . . H11D H 0.5003 -0.3471 0.3848 0.081 Uiso 0.526(11) 1 d PR . . C12 C 0.5855(4) -0.4174(7) 0.331(2) 0.080(4) Uani 0.474(11) 1 d PDU A 1 H12A H 0.6156 -0.4249 0.4224 0.121 Uiso 0.474(11) 1 calc PR A 1 H12B H 0.6029 -0.3879 0.2232 0.121 Uiso 0.474(11) 1 calc PR A 1 H12C H 0.5686 -0.4879 0.3056 0.121 Uiso 0.474(11) 1 calc PR A 1 C12' C 0.5588(5) -0.4212(7) 0.5238(15) 0.080(4) Uani 0.526(11) 1 d PDU A 2 H12D H 0.5466 -0.4936 0.4898 0.120 Uiso 0.526(11) 1 calc PR A 2 H12E H 0.5403 -0.4015 0.6362 0.120 Uiso 0.526(11) 1 calc PR A 2 H12F H 0.6012 -0.4193 0.5375 0.120 Uiso 0.526(11) 1 calc PR A 2 C13 C 0.65253(13) -0.1529(3) 0.6643(5) 0.0311(7) Uani 1 1 d . . . H13A H 0.6413 -0.2091 0.5801 0.047 Uiso 1 1 calc R . . H13B H 0.6577 -0.1845 0.7822 0.047 Uiso 1 1 calc R . . H13C H 0.6891 -0.1199 0.6259 0.047 Uiso 1 1 calc R . . C14 C 0.66435(13) 0.0148(2) 0.9098(4) 0.0248(7) Uani 1 1 d . . . C15 C 0.66844(14) -0.0741(2) 1.1906(4) 0.0299(7) Uani 1 1 d . . . H15A H 0.6440 -0.0692 1.2984 0.036 Uiso 1 1 calc R . . H15B H 0.7032 -0.0284 1.2083 0.036 Uiso 1 1 calc R . . C16 C 0.68701(16) -0.1882(3) 1.1624(5) 0.0377(8) Uani 1 1 d . . . H16A H 0.7066 -0.2146 1.2692 0.057 Uiso 1 1 calc R . . H16B H 0.7138 -0.1919 1.0616 0.057 Uiso 1 1 calc R . . H16C H 0.6527 -0.2326 1.1381 0.057 Uiso 1 1 calc R . . C17 C 0.66809(12) 0.2212(2) 0.6919(4) 0.0241(6) Uani 1 1 d . . . C18 C 0.72123(12) 0.2671(3) 0.6454(4) 0.0273(7) Uani 1 1 d . . . H18A H 0.7485 0.2266 0.5784 0.033 Uiso 1 1 calc R . . C19 C 0.73501(14) 0.3716(3) 0.6960(5) 0.0333(8) Uani 1 1 d . . . H19A H 0.7716 0.4020 0.6656 0.040 Uiso 1 1 calc R . . C20 C 0.69465(17) 0.4299(3) 0.7908(5) 0.0375(8) Uani 1 1 d . . . C21 C 0.64232(14) 0.3866(2) 0.8426(6) 0.0354(7) Uani 1 1 d . . . H21A H 0.6155 0.4277 0.9100 0.042 Uiso 1 1 calc R . . C22 C 0.62931(14) 0.2816(3) 0.7948(4) 0.0306(7) Uani 1 1 d . . . H22A H 0.5937 0.2504 0.8323 0.037 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 0.0878(3) 0.02676(19) 0.0582(3) -0.0054(2) -0.0032(3) -0.01260(18) O1 0.0481(15) 0.0334(13) 0.0578(17) 0.0063(12) 0.0036(13) 0.0168(11) O2 0.0340(13) 0.0501(16) 0.0486(17) -0.0099(13) -0.0008(12) -0.0194(12) O3 0.0400(13) 0.0342(14) 0.082(2) -0.0214(14) -0.0085(13) -0.0005(11) O4 0.0243(11) 0.0407(13) 0.0350(15) 0.0025(10) -0.0036(9) -0.0054(9) O5 0.0237(11) 0.0307(12) 0.0248(12) 0.0031(9) 0.0009(9) 0.0004(9) N1 0.0197(12) 0.0259(13) 0.0275(14) -0.0002(11) 0.0040(11) 0.0022(10) N2 0.0252(13) 0.0226(13) 0.0313(15) 0.0036(11) 0.0014(11) 0.0047(10) C1 0.0218(15) 0.0375(17) 0.0303(19) 0.0002(15) 0.0008(13) 0.0037(13) C2 0.0214(15) 0.0353(16) 0.0292(16) 0.0001(13) 0.0000(12) 0.0010(13) C3 0.0266(16) 0.0249(16) 0.0291(18) 0.0015(13) -0.0028(13) -0.0029(13) C4 0.0234(15) 0.0231(15) 0.0223(16) 0.0011(12) -0.0006(13) -0.0013(12) C5 0.0216(14) 0.0207(14) 0.0254(16) 0.0008(12) 0.0009(12) 0.0005(12) C6 0.0206(14) 0.0254(16) 0.0242(17) 0.0005(12) -0.0026(12) 0.0015(12) C7 0.0311(17) 0.0329(17) 0.026(2) 0.0015(13) 0.0012(13) -0.0033(13) C8 0.0426(18) 0.0261(15) 0.0281(18) 0.0021(16) -0.0001(16) -0.0011(12) C9 0.0399(19) 0.0278(16) 0.0308(18) 0.0018(14) -0.0020(15) 0.0050(14) C10 0.0333(18) 0.0285(17) 0.034(2) 0.0015(14) -0.0040(15) -0.0029(14) C11 0.069(3) 0.039(2) 0.095(4) -0.023(2) -0.029(3) 0.0043(19) C12 0.073(6) 0.039(5) 0.129(9) -0.018(5) -0.004(6) -0.006(4) C12' 0.099(7) 0.055(5) 0.087(7) 0.000(5) -0.031(6) -0.004(5) C13 0.0290(17) 0.0326(18) 0.0317(19) -0.0070(14) -0.0051(14) 0.0067(14) C14 0.0241(16) 0.0240(15) 0.0263(18) -0.0034(12) 0.0008(12) 0.0003(12) C15 0.0307(17) 0.0392(18) 0.0196(17) 0.0021(14) -0.0010(13) 0.0068(13) C16 0.044(2) 0.0352(19) 0.034(2) 0.0030(15) -0.0033(16) 0.0087(15) C17 0.0261(15) 0.0232(15) 0.0230(17) 0.0014(13) -0.0029(12) -0.0009(12) C18 0.0257(15) 0.0301(17) 0.0260(17) 0.0031(13) -0.0018(13) -0.0029(13) C19 0.0346(18) 0.0313(17) 0.034(2) 0.0043(15) -0.0017(15) -0.0085(14) C20 0.055(2) 0.0224(18) 0.035(2) 0.0031(13) -0.0059(17) -0.0046(15) C21 0.0487(19) 0.0299(15) 0.0275(18) -0.0011(17) 0.0060(17) 0.0037(13) C22 0.0353(17) 0.0292(17) 0.0273(19) 0.0000(12) 0.0045(13) -0.0003(14) _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 C20 1.904(3) . ? O1 C9 1.217(4) . ? O2 C10 1.210(4) . ? O3 C10 1.327(4) . ? O3 C11 1.473(4) . ? O4 C14 1.213(3) . ? O5 C14 1.332(3) . ? O5 C15 1.455(4) . ? N1 N2 1.435(3) . ? N1 C7 1.491(4) . ? N1 C6 1.497(4) . ? N2 C9 1.387(4) . ? N2 C1 1.392(4) . ? C1 C2 1.338(5) . ? C1 H1A 0.9500 . ? C2 C3 1.473(5) . ? C2 H2A 0.9500 . ? C3 C4 1.350(4) . ? C3 C10 1.499(4) . ? C4 C13 1.505(4) . ? C4 C5 1.522(4) . ? C5 C14 1.515(4) . ? C5 C6 1.542(4) . ? C5 H5A 1.0000 . ? C6 C17 1.511(4) . ? C6 H6A 1.0000 . ? C7 C8 1.527(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.501(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C11 C12 1.397(9) . ? C11 C12' 1.399(9) . ? C11 H11A 0.9601 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C11 H11D 0.9600 . ? C12 H11C 0.9706 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C12' H11B 0.9449 . ? C12' H12D 0.9800 . ? C12' H12E 0.9800 . ? C12' H12F 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C15 C16 1.501(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.393(4) . ? C17 C22 1.401(4) . ? C18 C19 1.394(4) . ? C18 H18A 0.9500 . ? C19 C20 1.379(5) . ? C19 H19A 0.9500 . ? C20 C21 1.375(5) . ? C21 C22 1.391(4) . ? C21 H21A 0.9500 . ? C22 H22A 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 C10 O3 C11 116.0(3) . . ? C14 O5 C15 118.3(2) . . ? N2 N1 C7 102.2(2) . . ? N2 N1 C6 111.1(2) . . ? C7 N1 C6 112.8(2) . . ? C9 N2 C1 122.3(3) . . ? C9 N2 N1 114.4(2) . . ? C1 N2 N1 121.6(2) . . ? C2 C1 N2 130.0(3) . . ? C2 C1 H1A 115.0 . . ? N2 C1 H1A 115.0 . . ? C1 C2 C3 129.6(3) . . ? C1 C2 H2A 115.2 . . ? C3 C2 H2A 115.2 . . ? C4 C3 C2 124.8(3) . . ? C4 C3 C10 123.5(3) . . ? C2 C3 C10 111.5(3) . . ? C3 C4 C13 126.1(3) . . ? C3 C4 C5 118.8(3) . . ? C13 C4 C5 115.1(2) . . ? C14 C5 C4 109.4(2) . . ? C14 C5 C6 111.4(2) . . ? C4 C5 C6 111.1(2) . . ? C14 C5 H5A 108.3 . . ? C4 C5 H5A 108.3 . . ? C6 C5 H5A 108.3 . . ? N1 C6 C17 114.1(2) . . ? N1 C6 C5 107.9(2) . . ? C17 C6 C5 114.1(3) . . ? N1 C6 H6A 106.7 . . ? C17 C6 H6A 106.7 . . ? C5 C6 H6A 106.7 . . ? N1 C7 C8 107.2(2) . . ? N1 C7 H7A 110.3 . . ? C8 C7 H7A 110.3 . . ? N1 C7 H7B 110.3 . . ? C8 C7 H7B 110.3 . . ? H7A C7 H7B 108.5 . . ? C9 C8 C7 102.3(2) . . ? C9 C8 H8A 111.3 . . ? C7 C8 H8A 111.3 . . ? C9 C8 H8B 111.3 . . ? C7 C8 H8B 111.3 . . ? H8A C8 H8B 109.2 . . ? O1 C9 N2 123.9(3) . . ? O1 C9 C8 128.8(3) . . ? N2 C9 C8 107.3(3) . . ? O2 C10 O3 122.4(3) . . ? O2 C10 C3 122.1(3) . . ? O3 C10 C3 115.4(3) . . ? C12 C11 C12' 68.7(8) . . ? C12 C11 O3 113.6(5) . . ? C12' C11 O3 106.5(5) . . ? C12 C11 H11A 111.0 . . ? C12' C11 H11A 139.9 . . ? O3 C11 H11A 109.4 . . ? C12 C11 H11B 106.3 . . ? C12' C11 H11B 42.3 . . ? O3 C11 H11B 108.4 . . ? H11A C11 H11B 107.9 . . ? C12 C11 H11C 43.9 . . ? C12' C11 H11C 111.1 . . ? O3 C11 H11C 111.4 . . ? H11A C11 H11C 71.3 . . ? H11B C11 H11C 137.8 . . ? C12 C11 H11D 134.9 . . ? C12' C11 H11D 109.0 . . ? O3 C11 H11D 110.1 . . ? H11A C11 H11D 41.1 . . ? H11B C11 H11D 69.0 . . ? H11C C11 H11D 108.7 . . ? C11 C12 H11C 43.3 . . ? C11 C12 H12A 109.5 . . ? H11C C12 H12A 144.7 . . ? C11 C12 H12B 109.5 . . ? H11C C12 H12B 72.3 . . ? C11 C12 H12C 109.5 . . ? H11C C12 H12C 102.4 . . ? C11 C12' H11B 43.1 . . ? C11 C12' H12D 109.5 . . ? H11B C12' H12D 99.6 . . ? C11 C12' H12E 109.5 . . ? H11B C12' H12E 74.2 . . ? H12D C12' H12E 109.5 . . ? C11 C12' H12F 109.5 . . ? H11B C12' H12F 146.7 . . ? H12D C12' H12F 109.5 . . ? H12E C12' H12F 109.5 . . ? C4 C13 H13A 109.5 . . ? C4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O4 C14 O5 124.4(3) . . ? O4 C14 C5 126.0(3) . . ? O5 C14 C5 109.6(2) . . ? O5 C15 C16 110.2(3) . . ? O5 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? O5 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? 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 . . ? C18 C17 C22 118.4(3) . . ? C18 C17 C6 119.8(3) . . ? C22 C17 C6 121.7(3) . . ? C17 C18 C19 121.0(3) . . ? C17 C18 H18A 119.5 . . ? C19 C18 H18A 119.5 . . ? C20 C19 C18 118.9(3) . . ? C20 C19 H19A 120.6 . . ? C18 C19 H19A 120.6 . . ? C21 C20 C19 121.9(3) . . ? C21 C20 Br1 119.1(3) . . ? C19 C20 Br1 119.0(3) . . ? C20 C21 C22 119.0(3) . . ? C20 C21 H21A 120.5 . . ? C22 C21 H21A 120.5 . . ? C21 C22 C17 120.9(3) . . ? C21 C22 H22A 119.6 . . ? C17 C22 H22A 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 C7 N1 N2 C9 -15.4(3) . . . . ? C6 N1 N2 C9 105.2(3) . . . . ? C7 N1 N2 C1 150.3(3) . . . . ? C6 N1 N2 C1 -89.2(3) . . . . ? C9 N2 C1 C2 169.9(4) . . . . ? N1 N2 C1 C2 5.3(5) . . . . ? N2 C1 C2 C3 -0.3(6) . . . . ? C1 C2 C3 C4 48.1(6) . . . . ? C1 C2 C3 C10 -137.9(4) . . . . ? C2 C3 C4 C13 -178.2(3) . . . . ? C10 C3 C4 C13 8.6(5) . . . . ? C2 C3 C4 C5 -0.4(5) . . . . ? C10 C3 C4 C5 -173.7(3) . . . . ? C3 C4 C5 C14 145.1(3) . . . . ? C13 C4 C5 C14 -36.9(3) . . . . ? C3 C4 C5 C6 -91.5(3) . . . . ? C13 C4 C5 C6 86.5(3) . . . . ? N2 N1 C6 C17 -61.1(3) . . . . ? C7 N1 C6 C17 53.0(3) . . . . ? N2 N1 C6 C5 66.9(3) . . . . ? C7 N1 C6 C5 -179.0(2) . . . . ? C14 C5 C6 N1 171.5(2) . . . . ? C4 C5 C6 N1 49.3(3) . . . . ? C14 C5 C6 C17 -60.6(3) . . . . ? C4 C5 C6 C17 177.2(2) . . . . ? N2 N1 C7 C8 24.5(3) . . . . ? C6 N1 C7 C8 -94.8(3) . . . . ? N1 C7 C8 C9 -24.9(3) . . . . ? C1 N2 C9 O1 12.5(5) . . . . ? N1 N2 C9 O1 178.0(3) . . . . ? C1 N2 C9 C8 -165.8(3) . . . . ? N1 N2 C9 C8 -0.2(4) . . . . ? C7 C8 C9 O1 -162.8(4) . . . . ? C7 C8 C9 N2 15.4(3) . . . . ? C11 O3 C10 O2 -9.1(5) . . . . ? C11 O3 C10 C3 174.7(3) . . . . ? C4 C3 C10 O2 146.4(3) . . . . ? C2 C3 C10 O2 -27.6(5) . . . . ? C4 C3 C10 O3 -37.3(5) . . . . ? C2 C3 C10 O3 148.6(3) . . . . ? C10 O3 C11 C12 -168.2(8) . . . . ? C10 O3 C11 C12' -94.7(7) . . . . ? C15 O5 C14 O4 -5.9(4) . . . . ? C15 O5 C14 C5 174.0(2) . . . . ? C4 C5 C14 O4 113.0(3) . . . . ? C6 C5 C14 O4 -10.1(4) . . . . ? C4 C5 C14 O5 -66.8(3) . . . . ? C6 C5 C14 O5 170.0(2) . . . . ? C14 O5 C15 C16 -92.9(3) . . . . ? N1 C6 C17 C18 -97.8(3) . . . . ? C5 C6 C17 C18 137.6(3) . . . . ? N1 C6 C17 C22 77.2(3) . . . . ? C5 C6 C17 C22 -47.4(4) . . . . ? C22 C17 C18 C19 -1.6(5) . . . . ? C6 C17 C18 C19 173.6(3) . . . . ? C17 C18 C19 C20 -1.0(5) . . . . ? C18 C19 C20 C21 2.6(5) . . . . ? C18 C19 C20 Br1 -178.9(2) . . . . ? C19 C20 C21 C22 -1.3(6) . . . . ? Br1 C20 C21 C22 -179.8(3) . . . . ? C20 C21 C22 C17 -1.5(5) . . . . ? C18 C17 C22 C21 2.9(5) . . . . ? C6 C17 C22 C21 -172.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 68.19 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.340 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.048