data_shelxl _audit_creation_method SHELXL-97 _publ_section_references ; CrystalClear, Rigaku Corp., (1999) Altomare, A., M. Burla, M. Camalli, G. Cascarano, C. Giacovazzo A. Guagliardi, A. Moliterni, G. Polidori & R. Spagna. (1999) J. Appl. Cryst. 32, 115-119. Sheldrick, G.M. SHELXL97. Program for crystal structure refinement. University of Gottingen, Germany, 1997. ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H24 Br N O2' _chemical_formula_weight 438.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 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' '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 ' _symmetry_Int_Tables_number 1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.5337(9) _cell_length_b 10.3702(6) _cell_length_c 13.3899(12) _cell_angle_alpha 69.135(8) _cell_angle_beta 82.489(10) _cell_angle_gamma 67.433(8) _cell_volume 1022.44(15) _cell_formula_units_Z 2 _cell_measurement_temperature 143(1) _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 2.030 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.7944 _diffrn_ambient_temperature 143(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method 'phi and omega rotations' _diffrn_reflns_number 13602 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5922 _reflns_number_gt 5465 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 1999)' _computing_data_reduction 'CrystalClear (Rigaku, 1999)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0552P)^2^+0.0833P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _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 0.000(9) _refine_ls_number_reflns 5922 _refine_ls_number_parameters 509 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 4.439 _refine_ls_shift/su_mean 0.009 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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1669(7) 1.2157(7) 0.4766(4) 0.0396(14) Uani 1 1 d . . . C2 C 0.0215(7) 1.2331(7) 0.5399(5) 0.0430(14) Uani 1 1 d . . . H2 H -0.0543 1.3271 0.5367 0.057 Uiso 1 1 calc R . . C3 C -0.0077(7) 1.1084(7) 0.6071(5) 0.0415(13) Uani 1 1 d . . . H3 H -0.1044 1.1189 0.6493 0.055 Uiso 1 1 calc R . . C4 C 0.1060(6) 0.9667(7) 0.6127(5) 0.0342(13) Uani 1 1 d . . . C5 C 0.2474(7) 0.9535(6) 0.5465(5) 0.0385(13) Uani 1 1 d . . . H5 H 0.3233 0.8599 0.5488 0.051 Uiso 1 1 calc R . . C6 C 0.2762(7) 1.0767(7) 0.4782(5) 0.0414(14) Uani 1 1 d . . . H6 H 0.3694 1.0665 0.4330 0.055 Uiso 1 1 calc R . . C7 C 0.0713(6) 0.8376(6) 0.6898(5) 0.0342(12) Uani 1 1 d . . . C8 C 0.1648(6) 0.5774(7) 0.7590(5) 0.0424(14) Uani 1 1 d . . . H8A H 0.0631 0.5742 0.7365 0.056 Uiso 1 1 calc R . . H8B H 0.1511 0.5750 0.8326 0.056 Uiso 1 1 calc R . . C9 C 0.3198(6) 0.4468(6) 0.7484(4) 0.0308(12) Uani 1 1 d . . . H9 H 0.3417 0.4634 0.6720 0.041 Uiso 1 1 calc R . . C10 C 0.4749(5) 0.4406(5) 0.7980(4) 0.0358(10) Uani 1 1 d . . . H10A H 0.4523 0.4316 0.8726 0.048 Uiso 1 1 calc R . . H10B H 0.4935 0.5329 0.7621 0.048 Uiso 1 1 calc R . . C11 C 0.6362(5) 0.3118(5) 0.7904(4) 0.0385(10) Uani 1 1 d . . . H11A H 0.6716 0.3301 0.7164 0.051 Uiso 1 1 calc R . . H11B H 0.7263 0.3058 0.8311 0.051 Uiso 1 1 calc R . . C12 C 0.6083(6) 0.1652(6) 0.8329(4) 0.0343(12) Uani 1 1 d . . . H12A H 0.5897 0.1401 0.9093 0.046 Uiso 1 1 calc R . . H12B H 0.7100 0.0880 0.8210 0.046 Uiso 1 1 calc R . . C13 C 0.4551(6) 0.1695(6) 0.7791(4) 0.0289(11) Uani 1 1 d . . . C14 C 0.4293(6) 0.0228(6) 0.8252(4) 0.0302(11) Uani 1 1 d . . . C15 C 0.5683(6) -0.1098(6) 0.8380(4) 0.0340(11) Uani 1 1 d . . . H15 H 0.6759 -0.1064 0.8197 0.045 Uiso 1 1 calc R . . C16 C 0.5494(6) -0.2459(6) 0.8774(4) 0.0354(11) Uani 1 1 d . . . C17 C 0.3870(7) -0.2533(7) 0.9019(4) 0.0420(13) Uani 1 1 d . . . H17 H 0.3731 -0.3442 0.9273 0.056 Uiso 1 1 calc R . . C18 C 0.2500(6) -0.1241(7) 0.8877(5) 0.0355(12) Uani 1 1 d . . . H18 H 0.1422 -0.1282 0.9031 0.047 Uiso 1 1 calc R . . C19 C 0.2674(6) 0.0120(6) 0.8513(4) 0.0344(12) Uani 1 1 d . . . C20 C 0.1120(6) 0.1495(6) 0.8397(5) 0.0471(14) Uani 1 1 d . . . H20A H 0.0792 0.1578 0.9099 0.063 Uiso 1 1 calc R . . H20B H 0.0199 0.1387 0.8120 0.063 Uiso 1 1 calc R . . C21 C 0.1340(5) 0.2917(5) 0.7670(4) 0.0391(10) Uani 1 1 d . . . H21A H 0.0373 0.3764 0.7739 0.052 Uiso 1 1 calc R . . H21B H 0.1401 0.2955 0.6932 0.052 Uiso 1 1 calc R . . C22 C 0.2959(6) 0.2977(6) 0.7976(4) 0.0330(12) Uani 1 1 d . . . H22 H 0.2900 0.2776 0.8750 0.044 Uiso 1 1 calc R . . C23 C 0.4937(7) 0.1940(7) 0.6591(4) 0.0392(13) Uani 1 1 d . . . H23A H 0.5935 0.1138 0.6514 0.059 Uiso 1 1 calc R . . H23B H 0.5123 0.2857 0.6265 0.059 Uiso 1 1 calc R . . H23C H 0.3993 0.1978 0.6247 0.059 Uiso 1 1 calc R . . C24 C 0.6959(6) -0.3831(5) 0.8954(4) 0.0394(11) Uani 1 1 d . . . N1 N 0.8118(6) -0.4905(5) 0.9123(4) 0.0542(11) Uani 1 1 d . . . O1 O -0.0520(5) 0.8468(5) 0.7461(4) 0.0502(11) Uani 1 1 d . . . O2 O 0.1939(4) 0.7088(4) 0.6914(3) 0.0400(9) Uani 1 1 d . . . Br1 Br 0.21570(5) 1.38402(4) 0.39049(4) 0.05183(17) Uani 1 1 d . . . C1' C 0.8109(7) -0.2135(7) 0.5083(5) 0.0371(13) Uani 1 1 d . . . C2' C 0.9432(7) -0.2281(7) 0.4357(5) 0.0484(16) Uani 1 1 d . . . H2' H 1.0116 -0.3210 0.4322 0.064 Uiso 1 1 calc R . . C3' C 0.9713(7) -0.1047(7) 0.3699(5) 0.0426(14) Uani 1 1 d . . . H3' H 1.0596 -0.1140 0.3210 0.057 Uiso 1 1 calc R . . C4' C 0.8696(7) 0.0363(7) 0.3742(5) 0.0350(13) Uani 1 1 d . . . C5' C 0.7389(7) 0.0470(7) 0.4480(5) 0.0423(14) Uani 1 1 d . . . H5' H 0.6693 0.1397 0.4514 0.056 Uiso 1 1 calc R . . C6' C 0.7103(7) -0.0769(7) 0.5159(5) 0.0420(14) Uani 1 1 d . . . H6' H 0.6243 -0.0687 0.5662 0.056 Uiso 1 1 calc R . . C7' C 0.9098(7) 0.1656(7) 0.3031(5) 0.0386(14) Uani 1 1 d . . . C8' C 0.8189(7) 0.4304(6) 0.2451(5) 0.0402(13) Uani 1 1 d . . . H8'1 H 0.8451 0.4361 0.1713 0.053 Uiso 1 1 calc R . . H8'2 H 0.9143 0.4321 0.2761 0.053 Uiso 1 1 calc R . . C9' C 0.6589(6) 0.5600(6) 0.2509(4) 0.0354(13) Uani 1 1 d . . . H9' H 0.5737 0.5718 0.2025 0.047 Uiso 1 1 calc R . . C10' C 0.5834(6) 0.5374(5) 0.3640(4) 0.0426(11) Uani 1 1 d . . . H10C H 0.5509 0.4513 0.3865 0.057 Uiso 1 1 calc R . . H10D H 0.6682 0.5197 0.4139 0.057 Uiso 1 1 calc R . . C11' C 0.4272(6) 0.6751(5) 0.3655(4) 0.0438(12) Uani 1 1 d . . . H11C H 0.3373 0.6839 0.3231 0.058 Uiso 1 1 calc R . . H11D H 0.3870 0.6617 0.4383 0.058 Uiso 1 1 calc R . . C12' C 0.4629(7) 0.8172(6) 0.3224(4) 0.0365(12) Uani 1 1 d . . . H12C H 0.5440 0.8134 0.3688 0.049 Uiso 1 1 calc R . . H12D H 0.3589 0.9003 0.3220 0.049 Uiso 1 1 calc R . . C13' C 0.5346(6) 0.8408(6) 0.2077(4) 0.0329(12) Uani 1 1 d . . . C14' C 0.5818(7) 0.9813(6) 0.1698(4) 0.0340(12) Uani 1 1 d . . . C15' C 0.4582(7) 1.1169(6) 0.1712(4) 0.0435(14) Uani 1 1 d . . . H15' H 0.3509 1.1201 0.1976 0.058 Uiso 1 1 calc R . . C16' C 0.4925(7) 1.2458(6) 0.1343(4) 0.0453(14) Uani 1 1 d . . . C17' C 0.6528(7) 1.2434(7) 0.0962(4) 0.0471(14) Uani 1 1 d . . . H17' H 0.6772 1.3294 0.0731 0.063 Uiso 1 1 calc R . . C18' C 0.7756(8) 1.1102(9) 0.0933(5) 0.0450(14) Uani 1 1 d . . . H18' H 0.8833 1.1075 0.0681 0.060 Uiso 1 1 calc R . . C19' C 0.7410(7) 0.9796(6) 0.1273(4) 0.0368(12) Uani 1 1 d . . . C20' C 0.8767(7) 0.8434(7) 0.1105(5) 0.0557(16) Uani 1 1 d . . . H20C H 0.9625 0.7989 0.1661 0.074 Uiso 1 1 calc R . . H20D H 0.9311 0.8723 0.0423 0.074 Uiso 1 1 calc R . . C21' C 0.8038(6) 0.7301(6) 0.1127(4) 0.0480(12) Uani 1 1 d . . . H21C H 0.7333 0.7670 0.0499 0.064 Uiso 1 1 calc R . . H21D H 0.8949 0.6386 0.1124 0.064 Uiso 1 1 calc R . . C22' C 0.6992(6) 0.7023(6) 0.2126(4) 0.0349(12) Uani 1 1 d . . . H22' H 0.7684 0.6921 0.2699 0.046 Uiso 1 1 calc R . . C23' C 0.4021(7) 0.8669(6) 0.1287(4) 0.0424(13) Uani 1 1 d . . . H23D H 0.3738 0.7801 0.1474 0.064 Uiso 1 1 calc R . . H23E H 0.4476 0.8871 0.0577 0.064 Uiso 1 1 calc R . . H23F H 0.3020 0.9499 0.1314 0.064 Uiso 1 1 calc R . . C24' C 0.3621(8) 1.3871(7) 0.1297(4) 0.0612(16) Uani 1 1 d . . . N1' N 0.2618(8) 1.5021(6) 0.1210(5) 0.093(2) Uani 1 1 d . . . O1' O 1.0376(5) 0.1592(5) 0.2510(3) 0.0486(11) Uani 1 1 d . . . O2' O 0.7868(4) 0.2940(4) 0.3050(3) 0.0382(9) Uani 1 1 d . . . Br1' Br 0.76426(5) -0.38251(4) 0.59919(3) 0.05068(17) Uani 1 1 d . . . 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 C1 0.048(3) 0.035(4) 0.034(3) -0.009(3) -0.007(3) -0.013(3) C2 0.043(3) 0.023(3) 0.057(3) -0.015(3) -0.005(3) -0.003(2) C3 0.039(3) 0.034(3) 0.052(3) -0.019(3) 0.001(2) -0.009(2) C4 0.027(2) 0.030(3) 0.044(3) -0.016(3) -0.007(2) -0.002(2) C5 0.039(3) 0.027(3) 0.045(3) -0.013(3) -0.002(3) -0.006(3) C6 0.036(3) 0.037(4) 0.048(3) -0.019(3) 0.001(3) -0.007(3) C7 0.030(3) 0.023(3) 0.047(3) -0.012(3) -0.004(2) -0.005(2) C8 0.029(2) 0.030(3) 0.069(4) -0.022(3) 0.000(3) -0.007(2) C9 0.029(2) 0.025(3) 0.038(3) -0.015(3) 0.000(2) -0.006(2) C10 0.031(2) 0.027(2) 0.050(3) -0.016(2) -0.0020(19) -0.0071(18) C11 0.029(2) 0.033(2) 0.056(3) -0.017(2) 0.001(2) -0.0132(19) C12 0.032(2) 0.024(3) 0.042(3) -0.010(2) -0.005(2) -0.005(2) C13 0.026(2) 0.023(3) 0.037(3) -0.012(2) -0.004(2) -0.006(2) C14 0.030(2) 0.034(3) 0.031(2) -0.015(2) 0.005(2) -0.013(2) C15 0.038(2) 0.024(2) 0.038(2) -0.008(2) 0.004(2) -0.014(2) C16 0.040(2) 0.032(3) 0.034(2) -0.012(2) 0.003(2) -0.014(2) C17 0.057(3) 0.041(3) 0.041(3) -0.020(3) 0.009(3) -0.028(3) C18 0.038(3) 0.042(3) 0.037(2) -0.019(2) 0.007(2) -0.022(3) C19 0.028(2) 0.040(3) 0.040(3) -0.020(2) -0.001(2) -0.011(2) C20 0.031(2) 0.042(3) 0.074(4) -0.026(3) 0.008(3) -0.015(2) C21 0.029(2) 0.036(3) 0.056(3) -0.022(2) -0.002(2) -0.0082(18) C22 0.026(2) 0.028(3) 0.044(3) -0.013(2) -0.004(2) -0.006(2) C23 0.045(3) 0.034(3) 0.034(3) -0.011(3) 0.001(2) -0.011(2) C24 0.051(3) 0.028(3) 0.046(3) -0.013(2) 0.005(2) -0.022(2) N1 0.055(3) 0.035(3) 0.068(3) -0.011(2) 0.003(2) -0.017(2) O1 0.0331(19) 0.036(3) 0.075(3) -0.021(2) 0.011(2) -0.0074(18) O2 0.0350(18) 0.024(2) 0.056(2) -0.015(2) 0.0005(18) -0.0048(16) Br1 0.0560(3) 0.0376(4) 0.0567(3) -0.0069(3) -0.0074(3) -0.0173(3) C1' 0.036(3) 0.030(3) 0.045(3) -0.014(3) -0.006(2) -0.009(3) C2' 0.043(3) 0.033(4) 0.067(4) -0.024(3) 0.000(3) -0.005(3) C3' 0.033(3) 0.030(3) 0.059(3) -0.019(3) 0.004(3) -0.003(2) C4' 0.035(3) 0.033(3) 0.040(3) -0.016(3) -0.003(2) -0.011(2) C5' 0.039(3) 0.040(4) 0.047(3) -0.026(3) -0.001(3) -0.003(3) C6' 0.043(3) 0.034(4) 0.046(3) -0.015(3) 0.000(3) -0.010(3) C7' 0.033(3) 0.042(4) 0.048(3) -0.026(3) -0.007(3) -0.009(3) C8' 0.040(3) 0.030(3) 0.048(3) -0.007(3) -0.005(2) -0.014(2) C9' 0.031(2) 0.031(3) 0.046(3) -0.014(3) 0.000(2) -0.012(2) C10' 0.046(2) 0.032(3) 0.045(3) -0.008(2) -0.002(2) -0.014(2) C11' 0.047(3) 0.036(3) 0.047(3) -0.013(2) 0.015(2) -0.020(2) C12' 0.048(3) 0.028(3) 0.034(3) -0.009(2) 0.005(2) -0.018(2) C13' 0.036(3) 0.032(3) 0.028(3) -0.006(2) 0.003(2) -0.014(2) C14' 0.042(3) 0.028(3) 0.032(2) -0.007(2) -0.002(2) -0.015(2) C15' 0.055(3) 0.035(3) 0.037(3) -0.008(2) 0.010(2) -0.020(2) C16' 0.062(3) 0.032(3) 0.040(3) -0.010(2) 0.005(3) -0.019(3) C17' 0.065(3) 0.047(4) 0.035(3) -0.009(3) 0.008(3) -0.034(3) C18' 0.048(3) 0.054(4) 0.041(3) -0.017(3) 0.006(2) -0.029(3) C19' 0.043(3) 0.035(3) 0.038(3) -0.011(2) 0.003(2) -0.021(2) C20' 0.047(3) 0.044(3) 0.074(4) -0.016(3) 0.013(3) -0.022(3) C21' 0.047(3) 0.047(3) 0.053(3) -0.020(3) 0.011(2) -0.021(2) C22' 0.036(3) 0.034(3) 0.035(3) -0.013(2) 0.004(2) -0.013(2) C23' 0.042(3) 0.039(3) 0.046(3) -0.018(3) -0.006(2) -0.009(2) C24' 0.083(4) 0.045(4) 0.050(3) -0.007(3) 0.020(3) -0.031(3) N1' 0.109(5) 0.032(3) 0.104(5) -0.010(3) 0.047(4) -0.018(3) O1' 0.037(2) 0.044(3) 0.060(3) -0.018(2) 0.0087(19) -0.0120(19) O2' 0.0346(18) 0.025(2) 0.050(2) -0.0125(19) 0.0000(17) -0.0061(16) Br1' 0.0597(3) 0.0350(3) 0.0520(3) -0.0094(3) -0.0046(3) -0.0148(3) 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 C6 1.378(8) . ? C1 C2 1.398(7) . ? C1 Br1 1.884(6) . ? C2 C3 1.380(9) . ? C3 C4 1.397(8) . ? C4 C5 1.393(7) . ? C4 C7 1.479(8) . ? C5 C6 1.371(9) . ? C7 O1 1.205(6) . ? C7 O2 1.339(6) . ? C8 O2 1.436(7) . ? C8 C9 1.522(7) . ? C9 C10 1.527(7) . ? C9 C22 1.532(7) . ? C10 C11 1.529(5) . ? C11 C12 1.523(7) . ? C12 C13 1.553(7) . ? C13 C14 1.515(7) . ? C13 C23 1.545(7) . ? C13 C22 1.561(7) . ? C14 C15 1.400(7) . ? C14 C19 1.417(6) . ? C15 C16 1.386(7) . ? C16 C17 1.406(7) . ? C16 C24 1.454(7) . ? C17 C18 1.368(9) . ? C18 C19 1.380(9) . ? C19 C20 1.503(7) . ? C20 C21 1.517(7) . ? C21 C22 1.521(6) . ? C24 N1 1.142(6) . ? C1' C6' 1.378(8) . ? C1' C2' 1.389(8) . ? C1' Br1' 1.898(6) . ? C2' C3' 1.360(9) . ? C3' C4' 1.403(8) . ? C4' C5' 1.388(7) . ? C4' C7' 1.476(8) . ? C5' C6' 1.373(9) . ? C7' O1' 1.208(6) . ? C7' O2' 1.349(7) . ? C8' O2' 1.466(6) . ? C8' C9' 1.521(8) . ? C9' C22' 1.538(7) . ? C9' C10' 1.540(6) . ? C10' C11' 1.539(6) . ? C11' C12' 1.514(7) . ? C12' C13' 1.547(6) . ? C13' C23' 1.531(8) . ? C13' C14' 1.553(7) . ? C13' C22' 1.565(7) . ? C14' C19' 1.398(7) . ? C14' C15' 1.402(8) . ? C15' C16' 1.382(8) . ? C16' C17' 1.390(7) . ? C16' C24' 1.446(8) . ? C17' C18' 1.388(10) . ? C18' C19' 1.400(9) . ? C19' C20' 1.513(8) . ? C20' C21' 1.517(7) . ? C21' C22' 1.510(6) . ? C24' N1' 1.146(7) . ? 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 C6 C1 C2 120.7(6) . . ? C6 C1 Br1 119.9(4) . . ? C2 C1 Br1 119.5(4) . . ? C3 C2 C1 118.9(5) . . ? C2 C3 C4 120.9(5) . . ? C5 C4 C3 118.7(6) . . ? C5 C4 C7 123.1(5) . . ? C3 C4 C7 118.3(5) . . ? C6 C5 C4 120.9(5) . . ? C5 C6 C1 119.9(5) . . ? O1 C7 O2 123.7(5) . . ? O1 C7 C4 124.0(5) . . ? O2 C7 C4 112.4(4) . . ? O2 C8 C9 106.5(4) . . ? C8 C9 C10 110.0(4) . . ? C8 C9 C22 113.5(4) . . ? C10 C9 C22 110.0(4) . . ? C9 C10 C11 113.1(4) . . ? C12 C11 C10 111.5(3) . . ? C11 C12 C13 112.9(4) . . ? C14 C13 C23 106.6(4) . . ? C14 C13 C12 111.2(4) . . ? C23 C13 C12 108.7(4) . . ? C14 C13 C22 111.0(4) . . ? C23 C13 C22 112.3(5) . . ? C12 C13 C22 107.1(4) . . ? C15 C14 C19 117.0(5) . . ? C15 C14 C13 119.8(4) . . ? C19 C14 C13 123.0(5) . . ? C16 C15 C14 121.6(4) . . ? C15 C16 C17 120.1(5) . . ? C15 C16 C24 121.0(4) . . ? C17 C16 C24 118.9(5) . . ? C18 C17 C16 118.7(5) . . ? C17 C18 C19 121.8(5) . . ? C18 C19 C14 120.7(5) . . ? C18 C19 C20 119.1(4) . . ? C14 C19 C20 120.2(5) . . ? C19 C20 C21 114.5(4) . . ? C20 C21 C22 109.4(4) . . ? C21 C22 C9 116.4(4) . . ? C21 C22 C13 110.9(4) . . ? C9 C22 C13 111.1(4) . . ? N1 C24 C16 178.0(6) . . ? C7 O2 C8 116.0(4) . . ? C6' C1' C2' 121.1(6) . . ? C6' C1' Br1' 118.5(4) . . ? C2' C1' Br1' 120.3(4) . . ? C3' C2' C1' 119.1(5) . . ? C2' C3' C4' 121.2(5) . . ? C5' C4' C3' 118.2(6) . . ? C5' C4' C7' 123.0(5) . . ? C3' C4' C7' 118.7(5) . . ? C6' C5' C4' 121.2(5) . . ? C5' C6' C1' 119.1(5) . . ? O1' C7' O2' 123.4(6) . . ? O1' C7' C4' 125.1(5) . . ? O2' C7' C4' 111.5(5) . . ? O2' C8' C9' 107.3(4) . . ? C8' C9' C22' 109.2(4) . . ? C8' C9' C10' 113.0(5) . . ? C22' C9' C10' 109.5(4) . . ? C11' C10' C9' 110.3(4) . . ? C12' C11' C10' 113.2(4) . . ? C11' C12' C13' 111.2(4) . . ? C23' C13' C12' 111.2(4) . . ? C23' C13' C14' 107.0(5) . . ? C12' C13' C14' 109.5(4) . . ? C23' C13' C22' 112.9(4) . . ? C12' C13' C22' 107.2(4) . . ? C14' C13' C22' 109.0(4) . . ? C19' C14' C15' 118.4(5) . . ? C19' C14' C13' 122.1(5) . . ? C15' C14' C13' 119.4(5) . . ? C16' C15' C14' 121.4(5) . . ? C15' C16' C17' 120.4(5) . . ? C15' C16' C24' 121.4(5) . . ? C17' C16' C24' 118.2(5) . . ? C18' C17' C16' 118.8(6) . . ? C17' C18' C19' 121.4(5) . . ? C14' C19' C18' 119.6(5) . . ? C14' C19' C20' 122.7(5) . . ? C18' C19' C20' 117.6(5) . . ? C19' C20' C21' 111.7(4) . . ? C22' C21' C20' 108.6(4) . . ? C21' C22' C9' 117.9(4) . . ? C21' C22' C13' 111.5(4) . . ? C9' C22' C13' 110.9(4) . . ? N1' C24' C16' 176.5(6) . . ? C7' O2' C8' 116.7(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.451 _refine_diff_density_min -0.658 _refine_diff_density_rms 0.065