# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 207/338 data_global _publ_contact_author ; Professor Akira Mori Institute of Advanced Material Study Kyushu University 6-1, Kasuga-koen, Kasuga Fukuoka 816-8580 Japan ; _publ_contact_author_email mori-a@cm.kyushu-u.ac.jp _publ_contact_author_fax '+81(92)583-7810' _publ_contact_author_phone '+81(92)58-7806' _publ_requested_journal 'Journal of the Chemical Society, Perkin Transaction 1' _publ_section_title ; Thermal Cycloaddition Reactions of 1,5-Azulenequinones and 1,7-Azulenequinones with Cyclic Dienes and Cycloheptatriene ; _publ_section_exptl_refinement ; All H atoms were located at ideal positions and were included in refinement, but restrained to ride on the atom to which they are bonded. Isotropic thermal factors of H atoms were held fixed to 1.2 times or 1.5 times (for methyl and hydroxyl groups) U~eq~ of the riding atoms. ; data_8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (5_a,7b_a,8_a,13_a,13a_a,16a_a,17_a)-7b-Bromo- 7b,8,13,13a,16a,17-hexahydro-5,8,13,17-tetraphenyl-5,17:8,13- diepoxynaphth[2',3'-2,3]azuleno[5,6-c][2]benzoxepin- 14(5H)-one ; _chemical_name_common ? _chemical_melting_point 99 _chemical_formula_moiety 'C50 H33 Br O4, C6 H6, 0.5(C6 H6), 0.5(C6 H6)' _chemical_formula_sum 'C62 H45 Br O4' _chemical_formula_weight 933.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.276(4) _cell_length_b 16.196(3) _cell_length_c 24.731(2) _cell_angle_alpha 90.00 _cell_angle_beta 112.660(10) _cell_angle_gamma 90.00 _cell_volume 9712(2) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 22 _cell_measurement_theta_max 45 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3872 _exptl_absorpt_coefficient_mu 1.534 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.571 _exptl_absorpt_correction_T_max 0.736 _exptl_absorpt_process_details ; empirical via \y scans (North, Phillips, & Mathews, 1968). Relative values of T max and T min are 0.9991 and 0.7747, respectively. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius FR590' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1.3 _diffrn_reflns_number 8470 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 65.03 _reflns_number_total 8254 _reflns_number_gt 6800 _reflns_threshold_expression >2_s(I) _computing_data_collection ; CAD-4 Software (Enraf-Nonius, 1989) ; _computing_cell_refinement ; CAD-4 Software (Enraf-Nonius, 1989) ; _computing_data_reduction ; MolEN (Fair, 1990) ; _computing_structure_solution ; SIR92 (Altomare, Burla, Camalli, Cascarano, Giacovazzo, Guagliardi & Polidori, 1994) ; _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_molecular_graphics 'Xtal_GX (Hall & du Boulay, 1995)' _computing_publication_material 'SHELXL93 (Sheldrick, 1993)' _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^)+(0.0781P)^2^+9.1308P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8254 _refine_ls_number_parameters 605 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1381 _refine_ls_wR_factor_gt 0.1292 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max .234 _refine_diff_density_min -.832 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 0.640901(13) 0.05514(2) 0.659099(12) 0.06629(13) Uani 1 1 d . . . O6 O 0.79437(7) -0.10892(11) 0.60260(7) 0.0517(4) Uani 1 1 d . . . O1 O 0.80542(7) -0.15902(10) 0.51995(7) 0.0481(4) Uani 1 1 d . . . O2 O 0.61132(7) 0.21053(11) 0.56427(8) 0.0505(4) Uani 1 1 d . . . O3 O 0.53068(7) -0.00750(14) 0.44974(8) 0.0626(5) Uani 1 1 d . . . C1 C 0.82362(12) 0.05275(17) 0.47973(14) 0.0609(7) Uani 1 1 d . . . H1 H 0.8009 0.0657 0.4413 0.073 Uiso 1 1 calc R . . C2 C 0.86378(14) 0.1070(2) 0.51387(18) 0.0782(9) Uani 1 1 d . . . H2 H 0.8682 0.1573 0.4981 0.094 Uiso 1 1 calc R . . C3 C 0.89787(15) 0.0879(2) 0.57160(18) 0.0837(11) Uani 1 1 d . . . H3 H 0.9243 0.1256 0.5937 0.100 Uiso 1 1 calc R . . C4 C 0.89260(13) 0.01355(19) 0.59598(15) 0.0709(9) Uani 1 1 d . . . H4 H 0.9153 0.0002 0.6343 0.085 Uiso 1 1 calc R . . C4a C 0.85249(11) -0.04041(16) 0.56157(12) 0.0526(6) Uani 1 1 d . . . C5 C 0.83415(10) -0.12301(15) 0.57581(10) 0.0492(6) Uani 1 1 d . . . C6a C 0.74735(10) -0.06960(14) 0.56801(10) 0.0442(5) Uani 1 1 d . . . C7 C 0.71688(10) -0.03145(15) 0.59335(10) 0.0454(6) Uani 1 1 d . . . H7 H 0.7316 -0.0250 0.6338 0.054 Uiso 1 1 calc R . . C7a C 0.66247(10) -0.00010(15) 0.56061(10) 0.0435(5) Uani 1 1 d . . . C7b C 0.63792(10) 0.07289(15) 0.57928(10) 0.0437(5) Uani 1 1 d . . . C8 C 0.66057(9) 0.16251(15) 0.57451(10) 0.0427(5) Uani 1 1 d . . . C8a C 0.66374(9) 0.16523(14) 0.51430(10) 0.0412(5) Uani 1 1 d . . . C9 C 0.70653(10) 0.16470(15) 0.49513(11) 0.0463(5) Uani 1 1 d . . . H9 H 0.7430 0.1609 0.5214 0.056 Uiso 1 1 calc R . . C10 C 0.69312(11) 0.17008(17) 0.43507(12) 0.0553(6) Uani 1 1 d . . . H10 H 0.7212 0.1709 0.4210 0.066 Uiso 1 1 calc R . . C11 C 0.63899(12) 0.17417(19) 0.39595(12) 0.0599(7) Uani 1 1 d . . . H11 H 0.6312 0.1771 0.3560 0.072 Uiso 1 1 calc R . . C12 C 0.59613(11) 0.17393(18) 0.41519(11) 0.0547(6) Uani 1 1 d . . . H12 H 0.5596 0.1762 0.3889 0.066 Uiso 1 1 calc R . . C12a C 0.60934(10) 0.17025(15) 0.47459(11) 0.0452(5) Uani 1 1 d . . . C13 C 0.57465(10) 0.16881(17) 0.51158(11) 0.0497(6) Uani 1 1 d . . . C13a C 0.57757(10) 0.07886(16) 0.53508(10) 0.0468(6) Uani 1 1 d . . . H13a H 0.5518 0.0712 0.5547 0.056 Uiso 1 1 calc R . . C14 C 0.57230(10) 0.00954(17) 0.49224(10) 0.0486(6) Uani 1 1 d . . . C14a C 0.62496(10) -0.03392(16) 0.50983(10) 0.0463(6) Uani 1 1 d . . . C15 C 0.63254(11) -0.10743(16) 0.48088(11) 0.0528(6) Uani 1 1 d . . . H15 H 0.6021 -0.1411 0.4622 0.063 Uiso 1 1 calc R . . C16 C 0.68074(11) -0.12952(16) 0.47961(10) 0.0508(6) Uani 1 1 d . . . H16 H 0.6848 -0.1811 0.4653 0.061 Uiso 1 1 calc R . . C16a C 0.72860(10) -0.07074(14) 0.50147(10) 0.0429(5) Uani 1 1 d . . . H16a H 0.7149 -0.0155 0.4868 0.051 Uiso 1 1 calc R . . C17 C 0.77651(10) -0.09066(15) 0.48320(10) 0.0462(5) Uani 1 1 d . . . C17a C 0.81845(10) -0.02137(16) 0.50470(11) 0.0490(6) Uani 1 1 d . . . C21 C 0.87771(11) -0.18207(16) 0.61296(11) 0.0548(7) Uani 1 1 d . . . C22 C 0.92276(13) -0.1944(2) 0.59882(15) 0.0719(8) Uani 1 1 d . . . H22 H 0.9263 -0.1641 0.5685 0.086 Uiso 1 1 calc R . . C23 C 0.96300(14) -0.2513(2) 0.62900(18) 0.0846(11) Uani 1 1 d . . . H23 H 0.9933 -0.2594 0.6189 0.102 Uiso 1 1 calc R . . C24 C 0.95785(16) -0.2956(2) 0.67376(19) 0.0916(13) Uani 1 1 d . . . H24 H 0.9850 -0.3334 0.6947 0.110 Uiso 1 1 calc R . . C25 C 0.91326(17) -0.2844(2) 0.68743(18) 0.0964(13) Uani 1 1 d . . . H25 H 0.9098 -0.3152 0.7175 0.116 Uiso 1 1 calc R . . C26 C 0.87241(14) -0.2275(2) 0.65725(14) 0.0749(9) Uani 1 1 d . . . H26 H 0.8419 -0.2205 0.6670 0.090 Uiso 1 1 calc R . . C27 C 0.70891(10) 0.19813(15) 0.62495(10) 0.0466(6) Uani 1 1 d . . . C28 C 0.76011(11) 0.16207(18) 0.64276(12) 0.0567(7) Uani 1 1 d . . . H28 H 0.7648 0.1140 0.6247 0.068 Uiso 1 1 calc R . . C29 C 0.80505(13) 0.1972(2) 0.68774(13) 0.0682(8) Uani 1 1 d . . . H29 H 0.8394 0.1718 0.7001 0.082 Uiso 1 1 calc R . . C30 C 0.79868(15) 0.2688(2) 0.71369(13) 0.0743(9) Uani 1 1 d . . . H30 H 0.8287 0.2927 0.7434 0.089 Uiso 1 1 calc R . . C31 C 0.74800(16) 0.3052(2) 0.69574(14) 0.0758(9) Uani 1 1 d . . . H31 H 0.7437 0.3539 0.7134 0.091 Uiso 1 1 calc R . . C32 C 0.70301(13) 0.27047(18) 0.65166(13) 0.0615(7) Uani 1 1 d . . . H32 H 0.6687 0.2958 0.6399 0.074 Uiso 1 1 calc R . . C33 C 0.51962(11) 0.2111(2) 0.48600(13) 0.0625(8) Uani 1 1 d . . . C34 C 0.51528(14) 0.2931(3) 0.4982(2) 0.0890(11) Uani 1 1 d . . . H34 H 0.5456 0.3208 0.5249 0.107 Uiso 1 1 calc R . . C35 C 0.46583(18) 0.3343(3) 0.4709(3) 0.1206(18) Uani 1 1 d . . . H35 H 0.4630 0.3897 0.4794 0.145 Uiso 1 1 calc R . . C36 C 0.42144(17) 0.2946(4) 0.4317(3) 0.124(2) Uani 1 1 d . . . H36 H 0.3887 0.3232 0.4127 0.149 Uiso 1 1 calc R . . C37 C 0.42457(15) 0.2123(4) 0.4201(2) 0.1155(18) Uani 1 1 d . . . H37 H 0.3939 0.1848 0.3940 0.139 Uiso 1 1 calc R . . C38 C 0.47393(13) 0.1704(3) 0.44766(17) 0.0855(11) Uani 1 1 d . . . H38 H 0.4762 0.1146 0.4402 0.103 Uiso 1 1 calc R . . C39 C 0.75887(10) -0.11417(16) 0.41915(10) 0.0489(6) Uani 1 1 d . . . C40 C 0.72508(13) -0.0620(2) 0.37647(12) 0.0648(8) Uani 1 1 d . . . H40 H 0.7119 -0.0139 0.3871 0.078 Uiso 1 1 calc R . . C41 C 0.71061(14) -0.0808(2) 0.31782(13) 0.0745(9) Uani 1 1 d . . . H41 H 0.6882 -0.0449 0.2892 0.089 Uiso 1 1 calc R . . C42 C 0.72916(13) -0.1520(2) 0.30165(12) 0.0738(9) Uani 1 1 d . . . H42 H 0.7196 -0.1643 0.2622 0.089 Uiso 1 1 calc R . . C43 C 0.76212(13) -0.2052(2) 0.34434(13) 0.0678(8) Uani 1 1 d . . . H43 H 0.7745 -0.2539 0.3336 0.081 Uiso 1 1 calc R . . C44 C 0.77689(11) -0.18650(18) 0.40306(12) 0.0560(6) Uani 1 1 d . . . H44 H 0.7990 -0.2227 0.4316 0.067 Uiso 1 1 calc R . . C45 C 0.8362(2) -0.0035(4) 0.7799(3) 0.1201(16) Uani 1 1 d . . . H45 H 0.8038 0.0225 0.7560 0.144 Uiso 1 1 calc R . . C46 C 0.8637(3) -0.0508(4) 0.7558(3) 0.144(2) Uani 1 1 d . . . H46 H 0.8504 -0.0578 0.7154 0.173 Uiso 1 1 calc R . . C47 C 0.9117(3) -0.0887(4) 0.7911(3) 0.147(2) Uani 1 1 d . . . H47 H 0.9306 -0.1226 0.7749 0.176 Uiso 1 1 calc R . . C48 C 0.9313(3) -0.0765(4) 0.8496(3) 0.138(2) Uani 1 1 d . . . H48 H 0.9647 -0.0999 0.8735 0.165 Uiso 1 1 calc R . . C49 C 0.9020(3) -0.0299(4) 0.8740(2) 0.1187(16) Uani 1 1 d . . . H49 H 0.9147 -0.0239 0.9144 0.142 Uiso 1 1 calc R . . C50 C 0.8552(2) 0.0068(3) 0.8391(2) 0.1125(15) Uani 1 1 d . . . H50 H 0.8356 0.0394 0.8553 0.135 Uiso 1 1 calc R . . C51 C 0.4482(2) 0.0143(3) 0.2458(4) 0.1196(17) Uani 1 1 d . . . H51 H 0.4117 0.0133 0.2425 0.144 Uiso 1 1 calc R . . C52 C 0.4885(3) 0.0151(3) 0.2985(2) 0.1113(16) Uani 1 1 d . . . H52 H 0.4803 0.0160 0.3319 0.134 Uiso 1 1 calc R . . C53 C 0.5407(3) 0.0147(3) 0.3035(2) 0.1157(18) Uani 1 1 d . . . H53 H 0.5693 0.0148 0.3403 0.139 Uiso 1 1 calc R . . C54 C 0.5000 0.2423(5) 0.2500 0.136(3) Uani 1 2 d S . . H54 H 0.5000 0.1849 0.2500 0.164 Uiso 1 2 calc SR . . C55 C 0.5252(3) 0.2826(6) 0.2198(3) 0.161(3) Uani 1 1 d . . . H55 H 0.5424 0.2536 0.1991 0.194 Uiso 1 1 calc R . . C56 C 0.4749(4) 0.3696(7) 0.2800(4) 0.184(4) Uani 1 1 d . . . H56 H 0.4579 0.3999 0.3003 0.221 Uiso 1 1 calc R . . C57 C 0.5000 0.4059(10) 0.2500 0.183(7) Uani 1 2 d S . . H57 H 0.5000 0.4633 0.2500 0.219 Uiso 1 2 calc SR . . 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 0.0747(2) 0.0886(2) 0.03869(17) 0.00242(13) 0.02531(14) -0.01744(16) O6 0.0548(10) 0.0519(10) 0.0351(8) 0.0045(7) 0.0026(7) 0.0013(8) O1 0.0516(9) 0.0413(9) 0.0368(8) -0.0004(7) 0.0009(7) 0.0002(7) O2 0.0452(9) 0.0582(10) 0.0495(10) 0.0012(8) 0.0197(8) -0.0013(8) O3 0.0454(10) 0.0894(14) 0.0440(10) -0.0015(9) 0.0070(8) -0.0218(10) C1 0.0613(17) 0.0546(16) 0.0669(18) 0.0127(13) 0.0248(14) 0.0017(13) C2 0.079(2) 0.0514(17) 0.104(3) 0.0085(17) 0.034(2) -0.0125(16) C3 0.076(2) 0.0572(18) 0.099(3) -0.0067(18) 0.0120(19) -0.0240(16) C4 0.0654(18) 0.0589(17) 0.0669(19) -0.0060(14) 0.0017(15) -0.0130(14) C4a 0.0516(14) 0.0444(13) 0.0517(15) -0.0025(11) 0.0087(12) -0.0034(11) C5 0.0522(14) 0.0442(13) 0.0378(12) -0.0006(10) 0.0025(11) -0.0042(11) C6a 0.0491(13) 0.0403(12) 0.0327(12) 0.0020(9) 0.0042(10) -0.0077(10) C7 0.0510(13) 0.0475(13) 0.0280(11) 0.0023(9) 0.0044(10) -0.0098(11) C7a 0.0493(13) 0.0466(13) 0.0317(11) 0.0050(9) 0.0124(10) -0.0145(10) C7b 0.0441(12) 0.0534(14) 0.0333(11) 0.0049(10) 0.0145(10) -0.0107(10) C8 0.0405(12) 0.0489(13) 0.0392(12) -0.0002(10) 0.0158(10) -0.0059(10) C8a 0.0430(12) 0.0412(12) 0.0395(12) 0.0032(9) 0.0160(10) -0.0084(10) C9 0.0438(12) 0.0467(13) 0.0497(14) 0.0019(11) 0.0195(11) -0.0104(10) C10 0.0595(15) 0.0615(16) 0.0548(15) 0.0030(12) 0.0328(13) -0.0138(13) C11 0.0647(17) 0.0743(18) 0.0426(14) 0.0060(13) 0.0227(13) -0.0160(14) C12 0.0496(14) 0.0664(16) 0.0432(13) 0.0092(12) 0.0123(11) -0.0126(12) C12a 0.0422(12) 0.0492(13) 0.0440(13) 0.0077(10) 0.0164(10) -0.0076(10) C13 0.0384(12) 0.0647(16) 0.0452(13) 0.0084(11) 0.0153(11) -0.0044(11) C13a 0.0384(12) 0.0629(15) 0.0398(12) 0.0069(11) 0.0160(10) -0.0113(11) C14 0.0444(13) 0.0625(15) 0.0379(12) 0.0060(11) 0.0147(11) -0.0191(11) C14a 0.0443(13) 0.0525(14) 0.0372(12) 0.0026(10) 0.0103(10) -0.0174(11) C15 0.0561(15) 0.0519(14) 0.0413(13) -0.0064(11) 0.0088(11) -0.0205(12) C16 0.0610(16) 0.0454(13) 0.0369(12) -0.0039(10) 0.0087(11) -0.0114(12) C16a 0.0486(13) 0.0409(12) 0.0305(11) 0.0012(9) 0.0059(10) -0.0045(10) C17 0.0513(14) 0.0437(12) 0.0350(12) 0.0025(10) 0.0071(10) 0.0008(11) C17a 0.0485(13) 0.0456(13) 0.0483(14) 0.0010(11) 0.0137(11) -0.0006(11) C21 0.0532(15) 0.0437(13) 0.0457(14) -0.0034(11) -0.0052(11) -0.0034(11) C22 0.0650(19) 0.0688(19) 0.0684(19) 0.0026(15) 0.0108(16) 0.0073(15) C23 0.0627(19) 0.072(2) 0.093(3) -0.010(2) 0.0015(18) 0.0097(16) C24 0.069(2) 0.067(2) 0.094(3) 0.006(2) -0.018(2) 0.0096(17) C25 0.088(3) 0.083(2) 0.087(3) 0.036(2) 0.000(2) 0.010(2) C26 0.0697(19) 0.072(2) 0.0653(19) 0.0208(16) 0.0059(15) 0.0040(16) C27 0.0500(14) 0.0500(13) 0.0386(12) 0.0012(10) 0.0158(11) -0.0117(11) C28 0.0497(14) 0.0594(16) 0.0535(15) -0.0015(12) 0.0118(12) -0.0106(12) C29 0.0559(16) 0.079(2) 0.0559(17) 0.0085(15) 0.0067(13) -0.0171(15) C30 0.080(2) 0.084(2) 0.0478(16) -0.0091(15) 0.0125(15) -0.0371(19) C31 0.093(2) 0.072(2) 0.0600(18) -0.0217(16) 0.0264(18) -0.0243(19) C32 0.0693(18) 0.0606(17) 0.0554(16) -0.0073(13) 0.0248(14) -0.0095(14) C33 0.0434(14) 0.082(2) 0.0660(18) 0.0227(15) 0.0251(13) 0.0040(14) C34 0.0589(19) 0.097(3) 0.112(3) 0.013(2) 0.033(2) 0.0167(18) C35 0.076(3) 0.115(4) 0.174(5) 0.036(3) 0.051(3) 0.033(3) C36 0.056(2) 0.150(5) 0.164(5) 0.073(4) 0.040(3) 0.034(3) C37 0.0480(19) 0.155(5) 0.121(4) 0.058(3) 0.008(2) -0.002(2) C38 0.0486(17) 0.104(3) 0.090(2) 0.029(2) 0.0102(16) -0.0010(17) C39 0.0481(13) 0.0571(14) 0.0358(12) -0.0006(11) 0.0099(10) 0.0006(11) C40 0.0714(19) 0.0761(19) 0.0408(14) 0.0035(13) 0.0147(13) 0.0204(15) C41 0.076(2) 0.100(2) 0.0368(14) 0.0066(15) 0.0112(14) 0.0262(18) C42 0.0725(19) 0.107(3) 0.0367(14) -0.0082(16) 0.0147(13) 0.0101(18) C43 0.0672(18) 0.079(2) 0.0543(17) -0.0128(15) 0.0203(14) 0.0095(15) C44 0.0527(15) 0.0641(16) 0.0453(14) -0.0030(12) 0.0121(12) 0.0049(13) C45 0.117(4) 0.123(4) 0.110(4) 0.007(3) 0.033(3) 0.003(3) C46 0.160(6) 0.174(6) 0.091(4) -0.019(4) 0.040(4) 0.010(5) C47 0.163(6) 0.145(5) 0.146(6) -0.029(4) 0.074(5) 0.026(4) C48 0.126(4) 0.114(4) 0.146(5) 0.009(4) 0.024(4) 0.033(3) C49 0.136(4) 0.115(4) 0.094(3) -0.004(3) 0.033(3) -0.004(3) C50 0.117(4) 0.100(3) 0.122(4) -0.009(3) 0.047(3) 0.006(3) C51 0.103(4) 0.096(3) 0.168(6) -0.001(4) 0.061(4) -0.019(3) C52 0.170(5) 0.090(3) 0.090(3) -0.004(3) 0.069(4) -0.019(4) C53 0.144(5) 0.079(3) 0.081(3) -0.001(2) -0.004(3) 0.000(3) C54 0.146(8) 0.091(5) 0.135(8) 0.000 0.011(6) 0.000 C55 0.127(5) 0.192(8) 0.124(6) -0.020(5) 0.003(4) -0.002(5) C56 0.159(8) 0.199(10) 0.128(7) -0.043(7) -0.018(5) 0.068(8) C57 0.185(16) 0.147(10) 0.139(13) 0.000 -0.021(10) 0.000 _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 C7b 1.966(2) . ? O6 C6a 1.360(3) . ? O6 C5 1.455(3) . ? O1 C5 1.419(3) . ? O1 C17 1.448(3) . ? O2 C8 1.446(3) . ? O2 C13 1.454(3) . ? O3 C14 1.221(3) . ? C1 C17a 1.380(4) . ? C1 C2 1.382(4) . ? C2 C3 1.397(5) . ? C3 C4 1.377(5) . ? C4 C4a 1.381(4) . ? C4a C17a 1.380(4) . ? C4a C5 1.509(4) . ? C5 C21 1.503(3) . ? C6a C7 1.343(4) . ? C6a C16a 1.525(3) . ? C7 C7a 1.437(3) . ? C7a C14a 1.377(3) . ? C7a C7b 1.502(4) . ? C7b C13a 1.544(3) . ? C7b C8 1.590(3) . ? C8 C27 1.510(3) . ? C8 C8a 1.524(3) . ? C8a C9 1.378(3) . ? C8a C12a 1.390(3) . ? C9 C10 1.391(4) . ? C10 C11 1.379(4) . ? C11 C12 1.381(4) . ? C12 C12a 1.374(4) . ? C12a C13 1.520(3) . ? C13 C33 1.502(4) . ? C13 C13a 1.559(4) . ? C13a C14 1.513(4) . ? C14 C14a 1.461(4) . ? C14a C15 1.442(4) . ? C15 C16 1.328(4) . ? C16 C16a 1.502(3) . ? C16a C17 1.527(4) . ? C17 C39 1.518(3) . ? C17 C17a 1.518(4) . ? C21 C26 1.371(4) . ? C21 C22 1.372(5) . ? C22 C23 1.385(5) . ? C23 C24 1.369(6) . ? C24 C25 1.351(6) . ? C25 C26 1.393(5) . ? C27 C28 1.374(4) . ? C27 C32 1.383(4) . ? C28 C29 1.394(4) . ? C29 C30 1.368(5) . ? C30 C31 1.364(5) . ? C31 C32 1.382(4) . ? C33 C34 1.377(5) . ? C33 C38 1.378(5) . ? C34 C35 1.383(5) . ? C35 C36 1.358(7) . ? C36 C37 1.372(8) . ? C37 C38 1.387(5) . ? C39 C40 1.376(4) . ? C39 C44 1.379(4) . ? C40 C41 1.384(4) . ? C41 C42 1.370(5) . ? C42 C43 1.380(4) . ? C43 C44 1.385(4) . ? C45 C46 1.340(8) . ? C45 C50 1.362(7) . ? C46 C47 1.371(8) . ? C47 C48 1.351(8) . ? C48 C49 1.369(8) . ? C49 C50 1.340(7) . ? C51 C52 1.326(8) . ? C51 C53 1.359(8) 2_655 ? C52 C53 1.329(7) . ? C53 C51 1.359(8) 2_655 ? C54 C55 1.343(9) 2_655 ? C54 C55 1.343(9) . ? C55 C56 1.409(12) 2_655 ? C56 C57 1.306(12) . ? C56 C55 1.409(12) 2_655 ? C57 C56 1.306(12) 2_655 ? 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 C6a O6 C5 115.14(18) . . ? C5 O1 C17 104.49(17) . . ? C8 O2 C13 98.41(18) . . ? C17a C1 C2 117.5(3) . . ? C1 C2 C3 121.4(3) . . ? C4 C3 C2 120.6(3) . . ? C3 C4 C4a 117.7(3) . . ? C17a C4a C4 121.8(3) . . ? C17a C4a C5 107.2(2) . . ? C4 C4a C5 130.8(3) . . ? O1 C5 O6 107.55(19) . . ? O1 C5 C21 109.1(2) . . ? O6 C5 C21 109.4(2) . . ? O1 C5 C4a 103.6(2) . . ? O6 C5 C4a 108.5(2) . . ? C21 C5 C4a 118.1(2) . . ? C7 C6a O6 118.8(2) . . ? C7 C6a C16a 120.4(2) . . ? O6 C6a C16a 120.7(2) . . ? C6a C7 C7a 122.8(2) . . ? C14a C7a C7 125.5(2) . . ? C14a C7a C7b 110.6(2) . . ? C7 C7a C7b 123.8(2) . . ? C7a C7b C13a 106.1(2) . . ? C7a C7b C8 118.57(19) . . ? C13a C7b C8 101.65(19) . . ? C7a C7b Br1 109.74(15) . . ? C13a C7b Br1 110.65(15) . . ? C8 C7b Br1 109.67(15) . . ? O2 C8 C27 110.5(2) . . ? O2 C8 C8a 101.27(18) . . ? C27 C8 C8a 116.80(19) . . ? O2 C8 C7b 99.71(17) . . ? C27 C8 C7b 120.46(19) . . ? C8a C8 C7b 105.17(18) . . ? C9 C8a C12a 120.7(2) . . ? C9 C8a C8 134.0(2) . . ? C12a C8a C8 105.29(19) . . ? C8a C9 C10 117.5(2) . . ? C11 C10 C9 121.4(2) . . ? C10 C11 C12 121.0(2) . . ? C12a C12 C11 117.7(2) . . ? C12 C12a C8a 121.7(2) . . ? C12 C12a C13 132.9(2) . . ? C8a C12a C13 105.4(2) . . ? O2 C13 C33 111.3(2) . . ? O2 C13 C12a 100.85(18) . . ? C33 C13 C12a 116.3(2) . . ? O2 C13 C13a 100.35(18) . . ? C33 C13 C13a 119.0(2) . . ? C12a C13 C13a 106.5(2) . . ? C14 C13a C7b 104.0(2) . . ? C14 C13a C13 117.0(2) . . ? C7b C13a C13 102.24(18) . . ? O3 C14 C14a 125.4(3) . . ? O3 C14 C13a 125.5(3) . . ? C14a C14 C13a 109.2(2) . . ? C7a C14a C15 126.4(2) . . ? C7a C14a C14 110.1(2) . . ? C15 C14a C14 123.1(2) . . ? C16 C15 C14a 123.3(2) . . ? C15 C16 C16a 119.6(2) . . ? C16 C16a C6a 105.88(19) . . ? C16 C16a C17 115.5(2) . . ? C6a C16a C17 111.18(19) . . ? O1 C17 C39 109.8(2) . . ? O1 C17 C17a 102.17(18) . . ? C39 C17 C17a 116.1(2) . . ? O1 C17 C16a 105.60(19) . . ? C39 C17 C16a 114.0(2) . . ? C17a C17 C16a 108.1(2) . . ? C4a C17a C1 120.9(2) . . ? C4a C17a C17 106.8(2) . . ? C1 C17a C17 132.0(2) . . ? C26 C21 C22 119.3(3) . . ? C26 C21 C5 122.8(3) . . ? C22 C21 C5 117.7(3) . . ? C21 C22 C23 120.9(4) . . ? C24 C23 C22 119.5(4) . . ? C25 C24 C23 119.8(3) . . ? C24 C25 C26 121.2(4) . . ? C21 C26 C25 119.3(4) . . ? C28 C27 C32 118.9(2) . . ? C28 C27 C8 120.7(2) . . ? C32 C27 C8 120.3(2) . . ? C27 C28 C29 120.4(3) . . ? C30 C29 C28 120.1(3) . . ? C31 C30 C29 119.6(3) . . ? C30 C31 C32 120.8(3) . . ? C31 C32 C27 120.1(3) . . ? C34 C33 C38 119.2(3) . . ? C34 C33 C13 119.7(3) . . ? C38 C33 C13 120.9(3) . . ? C33 C34 C35 120.0(4) . . ? C36 C35 C34 120.5(5) . . ? C35 C36 C37 120.4(4) . . ? C36 C37 C38 119.5(4) . . ? C33 C38 C37 120.4(4) . . ? C40 C39 C44 119.5(2) . . ? C40 C39 C17 119.6(2) . . ? C44 C39 C17 120.9(2) . . ? C39 C40 C41 120.3(3) . . ? C42 C41 C40 120.4(3) . . ? C41 C42 C43 119.4(3) . . ? C42 C43 C44 120.4(3) . . ? C39 C44 C43 120.0(3) . . ? C46 C45 C50 120.7(6) . . ? C45 C46 C47 119.6(6) . . ? C48 C47 C46 119.6(6) . . ? C47 C48 C49 120.3(6) . . ? C50 C49 C48 119.6(5) . . ? C49 C50 C45 120.2(5) . . ? C52 C51 C53 121.1(5) . 2_655 ? C51 C52 C53 119.8(5) . . ? C52 C53 C51 119.2(5) . 2_655 ? C55 C54 C55 121.8(10) 2_655 . ? C54 C55 C56 118.9(9) . 2_655 ? C57 C56 C55 117.0(13) . 2_655 ? C56 C57 C56 126.6(19) . 2_655 ? 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 C17a C1 C2 C3 -0.2(5) . . . . ? C1 C2 C3 C4 0.6(6) . . . . ? C2 C3 C4 C4a -0.4(6) . . . . ? C3 C4 C4a C17a -0.1(5) . . . . ? C3 C4 C4a C5 -176.0(3) . . . . ? C17 O1 C5 O6 77.2(2) . . . . ? C17 O1 C5 C21 -164.2(2) . . . . ? C17 O1 C5 C4a -37.6(2) . . . . ? C6a O6 C5 O1 -49.4(2) . . . . ? C6a O6 C5 C21 -167.84(19) . . . . ? C6a O6 C5 C4a 62.0(2) . . . . ? C17a C4a C5 O1 21.7(3) . . . . ? C4 C4a C5 O1 -162.0(3) . . . . ? C17a C4a C5 O6 -92.4(2) . . . . ? C4 C4a C5 O6 84.0(4) . . . . ? C17a C4a C5 C21 142.4(3) . . . . ? C4 C4a C5 C21 -41.2(4) . . . . ? C5 O6 C6a C7 -159.4(2) . . . . ? C5 O6 C6a C16a 22.3(3) . . . . ? O6 C6a C7 C7a -169.5(2) . . . . ? C16a C6a C7 C7a 8.8(4) . . . . ? C6a C7 C7a C14a 32.4(4) . . . . ? C6a C7 C7a C7b -150.6(2) . . . . ? C14a C7a C7b C13a 3.2(2) . . . . ? C7 C7a C7b C13a -174.3(2) . . . . ? C14a C7a C7b C8 -110.2(2) . . . . ? C7 C7a C7b C8 72.3(3) . . . . ? C14a C7a C7b Br1 122.73(18) . . . . ? C7 C7a C7b Br1 -54.7(3) . . . . ? C13 O2 C8 C27 174.41(18) . . . . ? C13 O2 C8 C8a 49.98(19) . . . . ? C13 O2 C8 C7b -57.77(19) . . . . ? C7a C7b C8 O2 150.06(19) . . . . ? C13a C7b C8 O2 34.3(2) . . . . ? Br1 C7b C8 O2 -82.85(17) . . . . ? C7a C7b C8 C27 -89.1(3) . . . . ? C13a C7b C8 C27 155.1(2) . . . . ? Br1 C7b C8 C27 38.0(3) . . . . ? C7a C7b C8 C8a 45.5(3) . . . . ? C13a C7b C8 C8a -70.3(2) . . . . ? Br1 C7b C8 C8a 172.56(15) . . . . ? O2 C8 C8a C9 148.4(3) . . . . ? C27 C8 C8a C9 28.4(4) . . . . ? C7b C8 C8a C9 -108.1(3) . . . . ? O2 C8 C8a C12a -30.6(2) . . . . ? C27 C8 C8a C12a -150.7(2) . . . . ? C7b C8 C8a C12a 72.8(2) . . . . ? C12a C8a C9 C10 0.5(4) . . . . ? C8 C8a C9 C10 -178.4(2) . . . . ? C8a C9 C10 C11 -1.2(4) . . . . ? C9 C10 C11 C12 0.7(4) . . . . ? C10 C11 C12 C12a 0.6(4) . . . . ? C11 C12 C12a C8a -1.3(4) . . . . ? C11 C12 C12a C13 -180.0(3) . . . . ? C9 C8a C12a C12 0.7(4) . . . . ? C8 C8a C12a C12 179.9(2) . . . . ? C9 C8a C12a C13 179.7(2) . . . . ? C8 C8a C12a C13 -1.0(3) . . . . ? C8 O2 C13 C33 -174.5(2) . . . . ? C8 O2 C13 C12a -50.5(2) . . . . ? C8 O2 C13 C13a 58.7(2) . . . . ? C12 C12a C13 O2 -149.0(3) . . . . ? C8a C12a C13 O2 32.2(2) . . . . ? C12 C12a C13 C33 -28.5(4) . . . . ? C8a C12a C13 C33 152.6(2) . . . . ? C12 C12a C13 C13a 106.7(3) . . . . ? C8a C12a C13 C13a -72.2(2) . . . . ? C7a C7b C13a C14 -2.0(2) . . . . ? C8 C7b C13a C14 122.64(19) . . . . ? Br1 C7b C13a C14 -120.94(17) . . . . ? C7a C7b C13a C13 -124.2(2) . . . . ? C8 C7b C13a C13 0.4(2) . . . . ? Br1 C7b C13a C13 116.86(17) . . . . ? O2 C13 C13a C14 -147.7(2) . . . . ? C33 C13 C13a C14 90.7(3) . . . . ? C12a C13 C13a C14 -43.0(3) . . . . ? O2 C13 C13a C7b -34.9(2) . . . . ? C33 C13 C13a C7b -156.4(2) . . . . ? C12a C13 C13a C7b 69.8(2) . . . . ? C7b C13a C14 O3 -179.8(2) . . . . ? C13 C13a C14 O3 -68.0(3) . . . . ? C7b C13a C14 C14a 0.3(2) . . . . ? C13 C13a C14 C14a 112.1(2) . . . . ? C7 C7a C14a C15 1.5(4) . . . . ? C7b C7a C14a C15 -175.9(2) . . . . ? C7 C7a C14a C14 174.4(2) . . . . ? C7b C7a C14a C14 -3.1(3) . . . . ? O3 C14 C14a C7a -178.2(2) . . . . ? C13a C14 C14a C7a 1.7(3) . . . . ? O3 C14 C14a C15 -5.1(4) . . . . ? C13a C14 C14a C15 174.8(2) . . . . ? C7a C14a C15 C16 -34.8(4) . . . . ? C14 C14a C15 C16 153.2(3) . . . . ? C14a C15 C16 C16a -9.0(4) . . . . ? C15 C16 C16a C6a 72.6(3) . . . . ? C15 C16 C16a C17 -163.9(2) . . . . ? C7 C6a C16a C16 -72.7(3) . . . . ? O6 C6a C16a C16 105.5(2) . . . . ? C7 C6a C16a C17 161.0(2) . . . . ? O6 C6a C16a C17 -20.7(3) . . . . ? C5 O1 C17 C39 162.4(2) . . . . ? C5 O1 C17 C17a 38.6(2) . . . . ? C5 O1 C17 C16a -74.3(2) . . . . ? C16 C16a C17 O1 -76.0(2) . . . . ? C6a C16a C17 O1 44.7(2) . . . . ? C16 C16a C17 C39 44.6(3) . . . . ? C6a C16a C17 C39 165.3(2) . . . . ? C16 C16a C17 C17a 175.3(2) . . . . ? C6a C16a C17 C17a -64.0(2) . . . . ? C4 C4a C17a C1 0.5(4) . . . . ? C5 C4a C17a C1 177.3(3) . . . . ? C4 C4a C17a C17 -174.5(3) . . . . ? C5 C4a C17a C17 2.3(3) . . . . ? C2 C1 C17a C4a -0.4(4) . . . . ? C2 C1 C17a C17 173.2(3) . . . . ? O1 C17 C17a C4a -24.8(3) . . . . ? C39 C17 C17a C4a -144.3(2) . . . . ? C16a C17 C17a C4a 86.2(2) . . . . ? O1 C17 C17a C1 160.9(3) . . . . ? C39 C17 C17a C1 41.5(4) . . . . ? C16a C17 C17a C1 -88.0(3) . . . . ? O1 C5 C21 C26 -104.6(3) . . . . ? O6 C5 C21 C26 12.9(3) . . . . ? C4a C5 C21 C26 137.6(3) . . . . ? O1 C5 C21 C22 71.0(3) . . . . ? O6 C5 C21 C22 -171.6(2) . . . . ? C4a C5 C21 C22 -46.9(3) . . . . ? C26 C21 C22 C23 -0.7(5) . . . . ? C5 C21 C22 C23 -176.3(3) . . . . ? C21 C22 C23 C24 -0.3(5) . . . . ? C22 C23 C24 C25 1.1(6) . . . . ? C23 C24 C25 C26 -0.8(6) . . . . ? C22 C21 C26 C25 0.9(5) . . . . ? C5 C21 C26 C25 176.3(3) . . . . ? C24 C25 C26 C21 -0.1(6) . . . . ? O2 C8 C27 C28 179.6(2) . . . . ? C8a C8 C27 C28 -65.4(3) . . . . ? C7b C8 C27 C28 64.2(3) . . . . ? O2 C8 C27 C32 -4.2(3) . . . . ? C8a C8 C27 C32 110.8(3) . . . . ? C7b C8 C27 C32 -119.6(3) . . . . ? C32 C27 C28 C29 1.2(4) . . . . ? C8 C27 C28 C29 177.3(2) . . . . ? C27 C28 C29 C30 -1.3(4) . . . . ? C28 C29 C30 C31 0.7(5) . . . . ? C29 C30 C31 C32 0.0(5) . . . . ? C30 C31 C32 C27 -0.2(5) . . . . ? C28 C27 C32 C31 -0.4(4) . . . . ? C8 C27 C32 C31 -176.6(3) . . . . ? O2 C13 C33 C34 23.4(4) . . . . ? C12a C13 C33 C34 -91.3(4) . . . . ? C13a C13 C33 C34 139.3(3) . . . . ? O2 C13 C33 C38 -160.4(3) . . . . ? C12a C13 C33 C38 84.9(3) . . . . ? C13a C13 C33 C38 -44.6(4) . . . . ? C38 C33 C34 C35 -1.8(6) . . . . ? C13 C33 C34 C35 174.5(4) . . . . ? C33 C34 C35 C36 -0.3(7) . . . . ? C34 C35 C36 C37 2.0(8) . . . . ? C35 C36 C37 C38 -1.6(8) . . . . ? C34 C33 C38 C37 2.2(6) . . . . ? C13 C33 C38 C37 -174.0(3) . . . . ? C36 C37 C38 C33 -0.5(7) . . . . ? O1 C17 C39 C40 172.4(2) . . . . ? C17a C17 C39 C40 -72.4(3) . . . . ? C16a C17 C39 C40 54.1(3) . . . . ? O1 C17 C39 C44 -8.6(3) . . . . ? C17a C17 C39 C44 106.6(3) . . . . ? C16a C17 C39 C44 -126.9(3) . . . . ? C44 C39 C40 C41 -1.9(5) . . . . ? C17 C39 C40 C41 177.2(3) . . . . ? C39 C40 C41 C42 0.8(5) . . . . ? C40 C41 C42 C43 0.5(6) . . . . ? C41 C42 C43 C44 -0.7(5) . . . . ? C40 C39 C44 C43 1.6(4) . . . . ? C17 C39 C44 C43 -177.4(3) . . . . ? C42 C43 C44 C39 -0.3(5) . . . . ? C50 C45 C46 C47 -0.4(10) . . . . ? C45 C46 C47 C48 -1.5(11) . . . . ? C46 C47 C48 C49 3.3(11) . . . . ? C47 C48 C49 C50 -3.2(10) . . . . ? C48 C49 C50 C45 1.3(9) . . . . ? C46 C45 C50 C49 0.5(9) . . . . ? C53 C51 C52 C53 -1.4(7) 2_655 . . . ? C51 C52 C53 C51 0.6(7) . . . 2_655 ? C55 C54 C55 C56 0.0(5) 2_655 . . 2_655 ? C55 C56 C57 C56 0.0(5) 2_655 . . 2_655 ? data_11 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (5_a,6_b,8b_b,9_a,14_a,14a_b,16_b,17_a)-8b-Bromo- 5,6,8b,9,14,14a,16,17-octahydro-5,9,14,17-tetraphenyl-5,17:9,14- diepoxybenzo[5',6']cyclodeca[1',2'-3,4]cyclopenta[1,2-b] naphthalene-15,18-dione ; _chemical_name_common ? _chemical_melting_point 167--168 _chemical_formula_moiety 'C50 H33 Br O4, C6 H6, C6 H6' _chemical_formula_sum 'C62 H45 Br O4' _chemical_formula_weight 933.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 41.133(9) _cell_length_b 12.545(2) _cell_length_c 18.353(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.29(2) _cell_angle_gamma 90.00 _cell_volume 9346(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 15 _cell_measurement_theta_min 21 _cell_measurement_theta_max 42 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3872 _exptl_absorpt_coefficient_mu 1.594 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.785 _exptl_absorpt_correction_T_max 0.923 _exptl_absorpt_process_details ; empirical via \y scans (North, Phillips, & Mathews, 1968). Relative values of T max and T min are 0.9987 and 0.8492, respectively. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius FR590' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 15.4 _diffrn_reflns_number 8232 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.0782 _diffrn_reflns_limit_h_min -47 _diffrn_reflns_limit_h_max 48 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 65.03 _reflns_number_total 7951 _reflns_number_gt 4697 _reflns_threshold_expression >2_s(I) _computing_data_collection ; CAD-4 Software (Enraf-Nonius, 1989) ; _computing_cell_refinement ; CAD-4 Software (Enraf-Nonius, 1989) ; _computing_data_reduction ; MolEN (Fair, 1990) ; _computing_structure_solution ; SIR92 (Altomare, Burla, Camalli, Cascarano, Giacovazzo, Guagliardi & Polidori, 1994) ; _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_molecular_graphics 'Xtal_GX (Hall & du Boulay, 1995)' _computing_publication_material 'SHELXL93 (Sheldrick, 1993)' _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^)+(0.1020P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7951 _refine_ls_number_parameters 604 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1307 _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.1820 _refine_ls_wR_factor_gt 0.1464 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max .931 _refine_diff_density_min -.823 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 0.715365(13) 0.26782(4) 0.14665(3) 0.04912(19) Uani 1 1 d . . . O1 O 0.66603(7) -0.0388(2) -0.09066(16) 0.0376(7) Uani 1 1 d . . . O2 O 0.62323(7) 0.2247(2) 0.03438(16) 0.0391(7) Uani 1 1 d . . . O3 O 0.62926(9) -0.0176(3) 0.1498(2) 0.0533(9) Uani 1 1 d . . . O4 O 0.71225(10) -0.2052(3) 0.07887(19) 0.0589(10) Uani 1 1 d . . . C1 C 0.63398(15) -0.3061(5) -0.0780(3) 0.0597(15) Uani 1 1 d . . . H1 H 0.6153 -0.3087 -0.0556 0.072 Uiso 1 1 calc R . . C2 C 0.64511(19) -0.3965(5) -0.1118(4) 0.0749(19) Uani 1 1 d . . . H2 H 0.6336 -0.4603 -0.1116 0.090 Uiso 1 1 calc R . . C3 C 0.67222(19) -0.3923(5) -0.1447(4) 0.0746(19) Uani 1 1 d . . . H3 H 0.6786 -0.4528 -0.1680 0.090 Uiso 1 1 calc R . . C4 C 0.69051(16) -0.3006(4) -0.1443(3) 0.0584(15) Uani 1 1 d . . . H4 H 0.7094 -0.2986 -0.1660 0.070 Uiso 1 1 calc R . . C4a C 0.68000(13) -0.2125(4) -0.1112(3) 0.0440(12) Uani 1 1 d . . . C5 C 0.69440(11) -0.1012(4) -0.1006(2) 0.0372(10) Uani 1 1 d . . . C6 C 0.71838(11) -0.0965(4) -0.0247(2) 0.0398(11) Uani 1 1 d . . . H6 H 0.7374 -0.1424 -0.0273 0.048 Uiso 1 1 calc R . . C7 C 0.72988(12) 0.0165(4) -0.0128(3) 0.0445(12) Uani 1 1 d . . . H7 H 0.7495 0.0332 -0.0291 0.053 Uiso 1 1 calc R . . C8 C 0.71554(12) 0.0961(4) 0.0182(3) 0.0424(11) Uani 1 1 d . . . H8 H 0.7254 0.1625 0.0157 0.051 Uiso 1 1 calc R . . C8a C 0.68693(10) 0.0947(4) 0.0552(2) 0.0353(10) Uani 1 1 d . . . C8b C 0.67700(11) 0.1965(4) 0.0912(2) 0.0366(10) Uani 1 1 d . . . C9 C 0.65459(10) 0.2740(4) 0.0355(2) 0.0381(10) Uani 1 1 d . . . C9a C 0.65060(12) 0.3755(4) 0.0782(3) 0.0444(12) Uani 1 1 d . . . C10 C 0.66253(14) 0.4785(4) 0.0761(3) 0.0558(14) Uani 1 1 d . . . H10 H 0.6761 0.4986 0.0425 0.067 Uiso 1 1 calc R . . C11 C 0.65318(17) 0.5512(5) 0.1274(4) 0.0688(17) Uani 1 1 d . . . H11 H 0.6605 0.6213 0.1273 0.083 Uiso 1 1 calc R . . C12 C 0.63390(17) 0.5211(5) 0.1765(4) 0.0749(19) Uani 1 1 d . . . H12 H 0.6284 0.5715 0.2096 0.090 Uiso 1 1 calc R . . C13 C 0.62199(14) 0.4184(5) 0.1797(3) 0.0580(14) Uani 1 1 d . . . H13 H 0.6090 0.3985 0.2146 0.070 Uiso 1 1 calc R . . C13a C 0.63035(12) 0.3467(4) 0.1284(3) 0.0485(12) Uani 1 1 d . . . C14 C 0.62135(12) 0.2298(4) 0.1129(3) 0.0444(11) Uani 1 1 d . . . C14a C 0.65192(11) 0.1605(4) 0.1414(3) 0.0397(11) Uani 1 1 d . . . H14a H 0.6602 0.1717 0.1940 0.048 Uiso 1 1 calc R . . C15 C 0.64624(11) 0.0427(4) 0.1219(3) 0.0409(11) Uani 1 1 d . . . C15a C 0.66696(11) 0.0127(4) 0.0655(2) 0.0360(10) Uani 1 1 d . . . C16 C 0.66588(11) -0.0976(4) 0.0341(2) 0.0385(10) Uani 1 1 d . . . H16 H 0.6546 -0.1444 0.0647 0.046 Uiso 1 1 calc R . . C17 C 0.64720(11) -0.1037(4) -0.0489(2) 0.0391(11) Uani 1 1 d . . . C17a C 0.65185(13) -0.2135(4) -0.0793(3) 0.0454(12) Uani 1 1 d . . . C18 C 0.70010(12) -0.1383(4) 0.0348(3) 0.0416(11) Uani 1 1 d . . . C19 C 0.71040(11) -0.0566(4) -0.1627(2) 0.0385(11) Uani 1 1 d . . . C20 C 0.74181(13) -0.0883(5) -0.1716(3) 0.0544(14) Uani 1 1 d . . . H20 H 0.7529 -0.1393 -0.1402 0.065 Uiso 1 1 calc R . . C21 C 0.75671(14) -0.0444(5) -0.2271(3) 0.0603(15) Uani 1 1 d . . . H21 H 0.7777 -0.0665 -0.2329 0.072 Uiso 1 1 calc R . . C22 C 0.74080(14) 0.0313(5) -0.2734(3) 0.0567(14) Uani 1 1 d . . . H22 H 0.7510 0.0606 -0.3105 0.068 Uiso 1 1 calc R . . C23 C 0.71014(14) 0.0632(4) -0.2649(3) 0.0545(13) Uani 1 1 d . . . H23 H 0.6993 0.1144 -0.2965 0.065 Uiso 1 1 calc R . . C24 C 0.69475(12) 0.0203(4) -0.2095(3) 0.0466(12) Uani 1 1 d . . . H24 H 0.6738 0.0435 -0.2040 0.056 Uiso 1 1 calc R . . C25 C 0.66267(11) 0.2836(4) -0.0417(2) 0.0375(10) Uani 1 1 d . . . C26 C 0.64141(12) 0.2444(4) -0.1006(3) 0.0458(12) Uani 1 1 d . . . H26 H 0.6218 0.2123 -0.0933 0.055 Uiso 1 1 calc R . . C27 C 0.64907(15) 0.2525(5) -0.1711(3) 0.0590(15) Uani 1 1 d . . . H27 H 0.6343 0.2275 -0.2112 0.071 Uiso 1 1 calc R . . C28 C 0.67844(15) 0.2973(4) -0.1824(3) 0.0600(15) Uani 1 1 d . . . H28 H 0.6838 0.3004 -0.2297 0.072 Uiso 1 1 calc R . . C29 C 0.69967(14) 0.3371(5) -0.1239(3) 0.0590(15) Uani 1 1 d . . . H29 H 0.7193 0.3686 -0.1314 0.071 Uiso 1 1 calc R . . C30 C 0.69201(12) 0.3306(4) -0.0532(3) 0.0506(13) Uani 1 1 d . . . H30 H 0.7065 0.3578 -0.0135 0.061 Uiso 1 1 calc R . . C31 C 0.58854(13) 0.1978(4) 0.1301(3) 0.0520(13) Uani 1 1 d . . . C32 C 0.58491(15) 0.1793(5) 0.2032(3) 0.0694(17) Uani 1 1 d . . . H32 H 0.6032 0.1801 0.2404 0.083 Uiso 1 1 calc R . . C33 C 0.55405(18) 0.1598(6) 0.2200(4) 0.085(2) Uani 1 1 d . . . H33 H 0.5516 0.1489 0.2689 0.101 Uiso 1 1 calc R . . C34 C 0.52707(18) 0.1563(6) 0.1661(5) 0.092(2) Uani 1 1 d . . . H34 H 0.5063 0.1422 0.1779 0.110 Uiso 1 1 calc R . . C35 C 0.53090(16) 0.1737(7) 0.0942(5) 0.093(2) Uani 1 1 d . . . H35 H 0.5126 0.1716 0.0571 0.112 Uiso 1 1 calc R . . C36 C 0.56144(14) 0.1941(5) 0.0764(4) 0.0664(16) Uani 1 1 d . . . H36 H 0.5637 0.2055 0.0274 0.080 Uiso 1 1 calc R . . C37 C 0.61227(12) -0.0647(4) -0.0582(3) 0.0450(12) Uani 1 1 d . . . C38 C 0.59944(13) 0.0013(4) -0.1160(3) 0.0534(13) Uani 1 1 d . . . H38 H 0.6128 0.0231 -0.1496 0.064 Uiso 1 1 calc R . . C39 C 0.56727(14) 0.0351(5) -0.1245(4) 0.0685(17) Uani 1 1 d . . . H39 H 0.5591 0.0810 -0.1629 0.082 Uiso 1 1 calc R . . C40 C 0.54749(14) 0.0016(6) -0.0773(4) 0.077(2) Uani 1 1 d . . . H40 H 0.5257 0.0241 -0.0838 0.093 Uiso 1 1 calc R . . C41 C 0.55891(14) -0.0644(7) -0.0205(4) 0.080(2) Uani 1 1 d . . . H41 H 0.5451 -0.0872 0.0118 0.096 Uiso 1 1 calc R . . C42 C 0.59151(13) -0.0975(5) -0.0110(3) 0.0645(16) Uani 1 1 d . . . H42 H 0.5995 -0.1427 0.0281 0.077 Uiso 1 1 calc R . . C43 C 0.5768(2) -0.2404(8) 0.1529(4) 0.092(2) Uani 1 1 d . . . H43 H 0.5994 -0.2410 0.1529 0.110 Uiso 1 1 calc R . . C44 C 0.5621(2) -0.1525(7) 0.1746(4) 0.089(2) Uani 1 1 d . . . H44 H 0.5746 -0.0922 0.1895 0.107 Uiso 1 1 calc R . . C45 C 0.5292(2) -0.1519(7) 0.1749(5) 0.092(2) Uani 1 1 d . . . H45 H 0.5192 -0.0906 0.1890 0.111 Uiso 1 1 calc R . . C46 C 0.5106(2) -0.2407(8) 0.1546(6) 0.108(3) Uani 1 1 d . . . H46 H 0.4881 -0.2402 0.1561 0.130 Uiso 1 1 calc R . . C47 C 0.5250(2) -0.3289(8) 0.1325(5) 0.114(3) Uani 1 1 d . . . H47 H 0.5127 -0.3898 0.1184 0.137 Uiso 1 1 calc R . . C48 C 0.5586(2) -0.3272(9) 0.1310(5) 0.108(3) Uani 1 1 d . . . H48 H 0.5687 -0.3869 0.1147 0.129 Uiso 1 1 calc R . . C49 C 0.4411(3) -0.4905(12) 0.0461(6) 0.141(4) Uani 1 1 d . . . H49 H 0.4370 -0.4795 -0.0047 0.169 Uiso 1 1 calc R . . C50 C 0.4303(3) -0.4196(10) 0.0883(8) 0.130(4) Uani 1 1 d . . . H50 H 0.4186 -0.3609 0.0673 0.156 Uiso 1 1 calc R . . C51 C 0.4362(2) -0.4313(11) 0.1617(8) 0.128(3) Uani 1 1 d . . . H51 H 0.4289 -0.3799 0.1919 0.154 Uiso 1 1 calc R . . C52 C 0.4529(3) -0.5190(14) 0.1921(7) 0.150(5) Uani 1 1 d . . . H52 H 0.4568 -0.5287 0.2430 0.179 Uiso 1 1 calc R . . C53 C 0.4640(4) -0.5937(10) 0.1453(11) 0.169(6) Uani 1 1 d . . . H53 H 0.4757 -0.6534 0.1648 0.203 Uiso 1 1 calc R . . C54 C 0.4577(4) -0.5785(11) 0.0717(8) 0.170(5) Uani 1 1 d . . . H54 H 0.4647 -0.6276 0.0395 0.204 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 0.0472(3) 0.0524(3) 0.0441(3) -0.0103(3) -0.0038(2) -0.0002(3) O1 0.0435(17) 0.0357(17) 0.0343(17) 0.0030(13) 0.0086(14) -0.0005(14) O2 0.0388(16) 0.0465(18) 0.0324(16) -0.0017(15) 0.0073(13) -0.0011(14) O3 0.058(2) 0.056(2) 0.050(2) 0.0002(18) 0.0211(18) -0.0039(18) O4 0.077(3) 0.059(2) 0.040(2) 0.0112(18) 0.0067(18) 0.0202(19) C1 0.076(4) 0.051(3) 0.050(3) 0.003(3) 0.003(3) -0.015(3) C2 0.110(5) 0.039(3) 0.070(4) -0.004(3) -0.002(4) -0.019(3) C3 0.113(6) 0.045(4) 0.063(4) -0.011(3) 0.007(4) 0.001(4) C4 0.081(4) 0.046(3) 0.048(3) -0.003(3) 0.009(3) 0.004(3) C4a 0.061(3) 0.039(3) 0.031(2) -0.005(2) 0.003(2) -0.004(2) C5 0.045(3) 0.035(2) 0.031(2) -0.0016(19) 0.006(2) 0.007(2) C6 0.043(3) 0.043(3) 0.033(2) -0.002(2) 0.004(2) 0.005(2) C7 0.042(3) 0.050(3) 0.040(3) -0.008(2) 0.001(2) -0.002(2) C8 0.050(3) 0.038(3) 0.039(3) -0.005(2) 0.009(2) -0.001(2) C8a 0.038(2) 0.041(3) 0.027(2) -0.001(2) 0.0055(19) 0.004(2) C8b 0.038(2) 0.035(2) 0.034(2) -0.0098(19) -0.0016(19) -0.0034(19) C9 0.036(2) 0.044(3) 0.033(2) -0.003(2) -0.0002(18) 0.001(2) C9a 0.047(3) 0.043(3) 0.040(3) -0.003(2) -0.004(2) 0.011(2) C10 0.062(3) 0.049(3) 0.052(3) -0.004(3) -0.001(3) 0.003(3) C11 0.085(4) 0.044(3) 0.073(4) -0.013(3) -0.002(4) 0.010(3) C12 0.090(5) 0.059(4) 0.072(5) -0.023(3) 0.003(4) 0.018(3) C13 0.065(4) 0.059(4) 0.050(3) -0.009(3) 0.013(3) 0.016(3) C13a 0.048(3) 0.053(3) 0.044(3) -0.005(2) 0.005(2) 0.011(2) C14 0.048(3) 0.051(3) 0.036(3) -0.004(2) 0.010(2) 0.003(2) C14a 0.048(3) 0.042(3) 0.031(2) 0.001(2) 0.011(2) 0.005(2) C15 0.041(3) 0.049(3) 0.033(3) 0.004(2) 0.006(2) 0.003(2) C15a 0.041(2) 0.038(3) 0.029(2) 0.003(2) 0.0044(19) 0.002(2) C16 0.043(3) 0.039(3) 0.032(2) 0.000(2) 0.003(2) -0.002(2) C17 0.047(3) 0.040(3) 0.029(2) 0.003(2) 0.002(2) -0.008(2) C17a 0.056(3) 0.037(3) 0.038(3) -0.002(2) -0.006(2) -0.005(2) C18 0.053(3) 0.038(3) 0.032(2) -0.004(2) 0.002(2) -0.002(2) C19 0.049(3) 0.040(3) 0.027(2) 0.000(2) 0.007(2) 0.000(2) C20 0.055(3) 0.065(4) 0.044(3) 0.000(3) 0.013(3) 0.012(3) C21 0.056(3) 0.078(4) 0.051(3) -0.013(3) 0.022(3) 0.000(3) C22 0.065(4) 0.071(4) 0.038(3) -0.008(3) 0.019(3) -0.013(3) C23 0.069(4) 0.054(3) 0.041(3) 0.006(2) 0.011(3) -0.001(3) C24 0.051(3) 0.053(3) 0.037(3) -0.002(2) 0.011(2) 0.000(2) C25 0.038(2) 0.038(3) 0.037(2) 0.001(2) 0.0064(19) 0.006(2) C26 0.050(3) 0.049(3) 0.038(3) 0.005(2) 0.008(2) -0.004(2) C27 0.075(4) 0.063(4) 0.037(3) -0.005(3) 0.005(3) -0.007(3) C28 0.082(4) 0.057(4) 0.044(3) 0.010(3) 0.018(3) 0.006(3) C29 0.062(3) 0.059(4) 0.060(4) 0.020(3) 0.021(3) 0.002(3) C30 0.048(3) 0.050(3) 0.052(3) 0.004(3) 0.004(2) -0.003(2) C31 0.051(3) 0.055(3) 0.056(3) 0.001(3) 0.026(3) 0.008(2) C32 0.062(4) 0.092(5) 0.060(4) 0.008(3) 0.027(3) 0.012(3) C33 0.081(5) 0.097(5) 0.088(5) 0.021(4) 0.052(4) 0.018(4) C34 0.066(4) 0.102(6) 0.120(7) 0.013(5) 0.055(5) 0.001(4) C35 0.046(4) 0.132(7) 0.105(6) -0.001(5) 0.022(4) -0.010(4) C36 0.051(3) 0.086(4) 0.064(4) -0.004(3) 0.016(3) -0.007(3) C37 0.045(3) 0.047(3) 0.042(3) -0.004(2) 0.005(2) -0.010(2) C38 0.050(3) 0.059(3) 0.049(3) 0.005(3) 0.003(2) 0.003(3) C39 0.056(4) 0.080(4) 0.066(4) 0.000(3) 0.000(3) 0.006(3) C40 0.040(3) 0.106(5) 0.083(5) -0.016(4) 0.003(3) 0.004(3) C41 0.045(3) 0.137(7) 0.059(4) 0.008(4) 0.010(3) -0.007(4) C42 0.052(3) 0.095(5) 0.045(3) 0.012(3) 0.004(3) -0.008(3) C43 0.078(5) 0.135(8) 0.061(4) 0.017(5) 0.007(4) 0.004(5) C44 0.092(6) 0.103(6) 0.074(5) 0.019(4) 0.015(4) -0.010(5) C45 0.084(5) 0.092(6) 0.102(6) 0.000(5) 0.017(4) 0.008(4) C46 0.077(5) 0.114(7) 0.132(8) 0.004(6) 0.013(5) 0.004(5) C47 0.099(6) 0.093(6) 0.141(8) -0.013(6) -0.005(6) -0.002(5) C48 0.102(6) 0.125(8) 0.091(6) -0.014(6) -0.002(5) 0.034(6) C49 0.172(11) 0.157(11) 0.089(7) -0.010(8) 0.009(7) 0.026(9) C50 0.113(8) 0.124(9) 0.150(11) 0.031(8) 0.014(8) 0.009(6) C51 0.102(7) 0.153(10) 0.131(10) -0.010(8) 0.022(7) 0.011(7) C52 0.131(10) 0.201(15) 0.109(9) 0.028(10) -0.003(7) -0.015(10) C53 0.193(14) 0.101(9) 0.200(16) 0.034(10) -0.010(13) 0.024(8) C54 0.241(16) 0.121(10) 0.144(12) -0.018(9) 0.024(11) 0.054(10) _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 C8b 1.952(4) . ? O1 C17 1.429(5) . ? O1 C5 1.441(5) . ? O2 C9 1.428(5) . ? O2 C14 1.457(5) . ? O3 C15 1.199(6) . ? O4 C18 1.216(6) . ? C1 C17a 1.377(7) . ? C1 C2 1.404(9) . ? C2 C3 1.352(9) . ? C3 C4 1.375(8) . ? C4 C4a 1.364(7) . ? C4a C17a 1.380(7) . ? C4a C5 1.517(6) . ? C5 C19 1.512(6) . ? C5 C6 1.574(6) . ? C6 C7 1.499(7) . ? C6 C18 1.515(7) . ? C7 C8 1.333(7) . ? C8 C8a 1.450(6) . ? C8a C15a 1.349(6) . ? C8a C8b 1.524(6) . ? C8b C14a 1.557(6) . ? C8b C9 1.593(6) . ? C9 C25 1.511(6) . ? C9 C9a 1.519(7) . ? C9a C10 1.384(7) . ? C9a C13a 1.386(7) . ? C10 C11 1.407(8) . ? C11 C12 1.347(9) . ? C12 C13 1.384(9) . ? C13 C13a 1.385(7) . ? C13a C14 1.527(7) . ? C14 C31 1.490(7) . ? C14 C14a 1.549(7) . ? C14a C15 1.530(7) . ? C15 C15a 1.491(6) . ? C15a C16 1.497(6) . ? C16 C18 1.495(6) . ? C16 C17 1.593(6) . ? C17 C37 1.501(7) . ? C17 C17a 1.509(7) . ? C19 C24 1.380(7) . ? C19 C20 1.387(7) . ? C20 C21 1.384(7) . ? C21 C22 1.369(8) . ? C22 C23 1.356(7) . ? C23 C24 1.390(7) . ? C25 C26 1.367(7) . ? C25 C30 1.390(7) . ? C26 C27 1.385(7) . ? C27 C28 1.378(8) . ? C28 C29 1.365(8) . ? C29 C30 1.385(7) . ? C31 C36 1.364(8) . ? C31 C32 1.394(8) . ? C32 C33 1.376(8) . ? C33 C34 1.363(10) . ? C34 C35 1.371(10) . ? C35 C36 1.372(8) . ? C37 C42 1.374(7) . ? C37 C38 1.381(7) . ? C38 C39 1.374(8) . ? C39 C40 1.348(9) . ? C40 C41 1.355(10) . ? C41 C42 1.388(8) . ? C43 C48 1.346(12) . ? C43 C44 1.348(11) . ? C44 C45 1.354(10) . ? C45 C46 1.368(11) . ? C46 C47 1.350(12) . ? C47 C48 1.384(12) . ? C49 C50 1.302(14) . ? C49 C54 1.343(15) . ? C50 C51 1.338(14) . ? C51 C52 1.368(16) . ? C52 C53 1.397(17) . ? C53 C54 1.347(17) . ? 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 C17 O1 C5 106.1(3) . . ? C9 O2 C14 99.1(3) . . ? C17a C1 C2 117.4(6) . . ? C3 C2 C1 121.2(6) . . ? C2 C3 C4 121.4(6) . . ? C4a C4 C3 117.9(6) . . ? C4 C4a C17a 122.0(5) . . ? C4 C4a C5 131.1(5) . . ? C17a C4a C5 106.8(4) . . ? O1 C5 C19 110.7(4) . . ? O1 C5 C4a 102.1(4) . . ? C19 C5 C4a 116.9(4) . . ? O1 C5 C6 105.8(3) . . ? C19 C5 C6 111.5(4) . . ? C4a C5 C6 108.9(4) . . ? C7 C6 C18 113.9(4) . . ? C7 C6 C5 107.6(4) . . ? C18 C6 C5 108.2(4) . . ? C8 C7 C6 128.3(5) . . ? C7 C8 C8a 129.7(5) . . ? C15a C8a C8 129.4(4) . . ? C15a C8a C8b 111.5(4) . . ? C8 C8a C8b 119.1(4) . . ? C8a C8b C14a 105.3(4) . . ? C8a C8b C9 113.7(4) . . ? C14a C8b C9 100.8(3) . . ? C8a C8b Br1 111.1(3) . . ? C14a C8b Br1 112.4(3) . . ? C9 C8b Br1 113.0(3) . . ? O2 C9 C25 110.9(3) . . ? O2 C9 C9a 101.4(4) . . ? C25 C9 C9a 118.4(4) . . ? O2 C9 C8b 99.9(3) . . ? C25 C9 C8b 117.3(4) . . ? C9a C9 C8b 106.3(3) . . ? C10 C9a C13a 121.1(5) . . ? C10 C9a C9 134.4(5) . . ? C13a C9a C9 104.5(4) . . ? C9a C10 C11 116.7(6) . . ? C12 C11 C10 121.3(6) . . ? C11 C12 C13 122.7(6) . . ? C12 C13 C13a 116.5(6) . . ? C13 C13a C9a 121.6(5) . . ? C13 C13a C14 132.1(5) . . ? C9a C13a C14 106.3(4) . . ? O2 C14 C31 113.1(4) . . ? O2 C14 C13a 100.2(4) . . ? C31 C14 C13a 114.8(4) . . ? O2 C14 C14a 98.0(3) . . ? C31 C14 C14a 119.4(4) . . ? C13a C14 C14a 108.5(4) . . ? C15 C14a C14 112.2(4) . . ? C15 C14a C8b 103.4(4) . . ? C14 C14a C8b 102.5(4) . . ? O3 C15 C15a 125.1(5) . . ? O3 C15 C14a 125.9(4) . . ? C15a C15 C14a 108.9(4) . . ? C8a C15a C15 109.6(4) . . ? C8a C15a C16 129.1(4) . . ? C15 C15a C16 121.1(4) . . ? C18 C16 C15a 110.1(4) . . ? C18 C16 C17 107.5(4) . . ? C15a C16 C17 113.1(4) . . ? O1 C17 C37 110.2(4) . . ? O1 C17 C17a 102.1(4) . . ? C37 C17 C17a 115.6(4) . . ? O1 C17 C16 105.4(3) . . ? C37 C17 C16 113.4(4) . . ? C17a C17 C16 109.1(4) . . ? C1 C17a C4a 120.1(5) . . ? C1 C17a C17 131.6(5) . . ? C4a C17a C17 108.3(4) . . ? O4 C18 C16 121.8(4) . . ? O4 C18 C6 121.3(5) . . ? C16 C18 C6 116.8(4) . . ? C24 C19 C20 118.4(4) . . ? C24 C19 C5 120.8(4) . . ? C20 C19 C5 120.7(4) . . ? C21 C20 C19 120.3(5) . . ? C22 C21 C20 120.6(5) . . ? C23 C22 C21 119.6(5) . . ? C22 C23 C24 120.8(5) . . ? C19 C24 C23 120.3(5) . . ? C26 C25 C30 119.5(4) . . ? C26 C25 C9 120.2(4) . . ? C30 C25 C9 120.3(4) . . ? C25 C26 C27 120.0(5) . . ? C28 C27 C26 120.5(5) . . ? C29 C28 C27 119.8(5) . . ? C28 C29 C30 120.1(5) . . ? C29 C30 C25 120.1(5) . . ? C36 C31 C32 119.2(5) . . ? C36 C31 C14 121.3(5) . . ? C32 C31 C14 119.3(5) . . ? C33 C32 C31 119.4(6) . . ? C34 C33 C32 121.1(7) . . ? C33 C34 C35 119.1(6) . . ? C34 C35 C36 120.7(7) . . ? C31 C36 C35 120.5(6) . . ? C42 C37 C38 117.7(5) . . ? C42 C37 C17 120.8(5) . . ? C38 C37 C17 121.5(4) . . ? C39 C38 C37 121.0(5) . . ? C40 C39 C38 120.0(6) . . ? C39 C40 C41 121.0(6) . . ? C40 C41 C42 119.2(6) . . ? C37 C42 C41 121.1(6) . . ? C48 C43 C44 119.7(8) . . ? C43 C44 C45 120.1(8) . . ? C44 C45 C46 120.7(8) . . ? C47 C46 C45 119.7(8) . . ? C46 C47 C48 118.7(9) . . ? C43 C48 C47 121.1(9) . . ? C50 C49 C54 123.7(12) . . ? C49 C50 C51 120.1(12) . . ? C50 C51 C52 119.7(12) . . ? C51 C52 C53 118.8(12) . . ? C54 C53 C52 119.5(13) . . ? C49 C54 C53 118.2(13) . . ? 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 C17a C1 C2 C3 -0.3(9) . . . . ? C1 C2 C3 C4 2.0(10) . . . . ? C2 C3 C4 C4a -1.6(9) . . . . ? C3 C4 C4a C17a -0.5(8) . . . . ? C3 C4 C4a C5 179.2(5) . . . . ? C17 O1 C5 C19 162.4(4) . . . . ? C17 O1 C5 C4a 37.2(4) . . . . ? C17 O1 C5 C6 -76.7(4) . . . . ? C4 C4a C5 O1 157.4(5) . . . . ? C17a C4a C5 O1 -22.9(5) . . . . ? C4 C4a C5 C19 36.4(7) . . . . ? C17a C4a C5 C19 -143.9(4) . . . . ? C4 C4a C5 C6 -91.1(6) . . . . ? C17a C4a C5 C6 88.7(5) . . . . ? O1 C5 C6 C7 -66.1(4) . . . . ? C19 C5 C6 C7 54.3(5) . . . . ? C4a C5 C6 C7 -175.2(4) . . . . ? O1 C5 C6 C18 57.3(5) . . . . ? C19 C5 C6 C18 177.7(4) . . . . ? C4a C5 C6 C18 -51.8(5) . . . . ? C18 C6 C7 C8 -32.8(7) . . . . ? C5 C6 C7 C8 87.1(6) . . . . ? C6 C7 C8 C8a 6.5(9) . . . . ? C7 C8 C8a C15a -2.3(9) . . . . ? C7 C8 C8a C8b 175.4(5) . . . . ? C15a C8a C8b C14a 12.2(5) . . . . ? C8 C8a C8b C14a -166.0(4) . . . . ? C15a C8a C8b C9 -97.2(5) . . . . ? C8 C8a C8b C9 84.7(5) . . . . ? C15a C8a C8b Br1 134.1(3) . . . . ? C8 C8a C8b Br1 -44.0(5) . . . . ? C14 O2 C9 C25 -177.8(4) . . . . ? C14 O2 C9 C9a -51.1(4) . . . . ? C14 O2 C9 C8b 57.9(4) . . . . ? C8a C8b C9 O2 81.5(4) . . . . ? C14a C8b C9 O2 -30.6(4) . . . . ? Br1 C8b C9 O2 -150.8(3) . . . . ? C8a C8b C9 C25 -38.3(5) . . . . ? C14a C8b C9 C25 -150.5(4) . . . . ? Br1 C8b C9 C25 89.4(4) . . . . ? C8a C8b C9 C9a -173.4(4) . . . . ? C14a C8b C9 C9a 74.5(4) . . . . ? Br1 C8b C9 C9a -45.6(4) . . . . ? O2 C9 C9a C10 -147.2(5) . . . . ? C25 C9 C9a C10 -25.7(8) . . . . ? C8b C9 C9a C10 108.7(6) . . . . ? O2 C9 C9a C13a 33.4(4) . . . . ? C25 C9 C9a C13a 154.9(4) . . . . ? C8b C9 C9a C13a -70.6(4) . . . . ? C13a C9a C10 C11 0.3(8) . . . . ? C9 C9a C10 C11 -179.0(5) . . . . ? C9a C10 C11 C12 0.8(9) . . . . ? C10 C11 C12 C13 -0.3(10) . . . . ? C11 C12 C13 C13a -1.2(9) . . . . ? C12 C13 C13a C9a 2.3(8) . . . . ? C12 C13 C13a C14 -177.8(5) . . . . ? C10 C9a C13a C13 -1.9(8) . . . . ? C9 C9a C13a C13 177.6(5) . . . . ? C10 C9a C13a C14 178.2(4) . . . . ? C9 C9a C13a C14 -2.3(5) . . . . ? C9 O2 C14 C31 171.7(4) . . . . ? C9 O2 C14 C13a 49.0(4) . . . . ? C9 O2 C14 C14a -61.5(4) . . . . ? C13 C13a C14 O2 151.5(5) . . . . ? C9a C13a C14 O2 -28.7(5) . . . . ? C13 C13a C14 C31 30.0(8) . . . . ? C9a C13a C14 C31 -150.1(4) . . . . ? C13 C13a C14 C14a -106.5(6) . . . . ? C9a C13a C14 C14a 73.4(5) . . . . ? O2 C14 C14a C15 -71.1(4) . . . . ? C31 C14 C14a C15 51.1(6) . . . . ? C13a C14 C14a C15 -174.7(4) . . . . ? O2 C14 C14a C8b 39.2(4) . . . . ? C31 C14 C14a C8b 161.4(4) . . . . ? C13a C14 C14a C8b -64.4(5) . . . . ? C8a C8b C14a C15 -7.2(4) . . . . ? C9 C8b C14a C15 111.2(4) . . . . ? Br1 C8b C14a C15 -128.3(3) . . . . ? C8a C8b C14a C14 -124.0(4) . . . . ? C9 C8b C14a C14 -5.6(4) . . . . ? Br1 C8b C14a C14 114.9(3) . . . . ? C14 C14a C15 O3 -72.9(6) . . . . ? C8b C14a C15 O3 177.4(5) . . . . ? C14 C14a C15 C15a 110.6(4) . . . . ? C8b C14a C15 C15a 0.9(5) . . . . ? C8 C8a C15a C15 166.1(4) . . . . ? C8b C8a C15a C15 -11.8(5) . . . . ? C8 C8a C15a C16 -8.3(8) . . . . ? C8b C8a C15a C16 173.8(4) . . . . ? O3 C15 C15a C8a -169.8(5) . . . . ? C14a C15 C15a C8a 6.7(5) . . . . ? O3 C15 C15a C16 5.2(7) . . . . ? C14a C15 C15a C16 -178.3(4) . . . . ? C8a C15a C16 C18 41.1(6) . . . . ? C15 C15a C16 C18 -132.7(4) . . . . ? C8a C15a C16 C17 -79.1(6) . . . . ? C15 C15a C16 C17 107.1(5) . . . . ? C5 O1 C17 C37 -159.9(4) . . . . ? C5 O1 C17 C17a -36.5(4) . . . . ? C5 O1 C17 C16 77.4(4) . . . . ? C18 C16 C17 O1 -59.2(4) . . . . ? C15a C16 C17 O1 62.5(5) . . . . ? C18 C16 C17 C37 -179.8(4) . . . . ? C15a C16 C17 C37 -58.1(5) . . . . ? C18 C16 C17 C17a 49.8(5) . . . . ? C15a C16 C17 C17a 171.5(4) . . . . ? C2 C1 C17a C4a -1.7(8) . . . . ? C2 C1 C17a C17 -179.9(5) . . . . ? C4 C4a C17a C1 2.1(8) . . . . ? C5 C4a C17a C1 -177.6(5) . . . . ? C4 C4a C17a C17 -179.3(5) . . . . ? C5 C4a C17a C17 1.0(5) . . . . ? O1 C17 C17a C1 -160.1(5) . . . . ? C37 C17 C17a C1 -40.5(8) . . . . ? C16 C17 C17a C1 88.7(6) . . . . ? O1 C17 C17a C4a 21.5(5) . . . . ? C37 C17 C17a C4a 141.1(4) . . . . ? C16 C17 C17a C4a -89.7(5) . . . . ? C15a C16 C18 O4 105.8(5) . . . . ? C17 C16 C18 O4 -130.6(5) . . . . ? C15a C16 C18 C6 -77.3(5) . . . . ? C17 C16 C18 C6 46.3(5) . . . . ? C7 C6 C18 O4 -109.4(5) . . . . ? C5 C6 C18 O4 131.1(5) . . . . ? C7 C6 C18 C16 73.7(5) . . . . ? C5 C6 C18 C16 -45.9(5) . . . . ? O1 C5 C19 C24 -11.3(6) . . . . ? C4a C5 C19 C24 105.0(5) . . . . ? C6 C5 C19 C24 -128.8(5) . . . . ? O1 C5 C19 C20 165.6(4) . . . . ? C4a C5 C19 C20 -78.1(6) . . . . ? C6 C5 C19 C20 48.1(6) . . . . ? C24 C19 C20 C21 -0.8(8) . . . . ? C5 C19 C20 C21 -177.8(5) . . . . ? C19 C20 C21 C22 0.5(9) . . . . ? C20 C21 C22 C23 -0.2(9) . . . . ? C21 C22 C23 C24 0.3(8) . . . . ? C20 C19 C24 C23 0.9(7) . . . . ? C5 C19 C24 C23 177.9(5) . . . . ? C22 C23 C24 C19 -0.7(8) . . . . ? O2 C9 C25 C26 -1.9(6) . . . . ? C9a C9 C25 C26 -118.5(5) . . . . ? C8b C9 C25 C26 111.9(5) . . . . ? O2 C9 C25 C30 179.3(4) . . . . ? C9a C9 C25 C30 62.7(6) . . . . ? C8b C9 C25 C30 -66.9(6) . . . . ? C30 C25 C26 C27 -0.6(7) . . . . ? C9 C25 C26 C27 -179.4(5) . . . . ? C25 C26 C27 C28 1.8(8) . . . . ? C26 C27 C28 C29 -2.1(9) . . . . ? C27 C28 C29 C30 1.2(9) . . . . ? C28 C29 C30 C25 0.0(8) . . . . ? C26 C25 C30 C29 -0.3(7) . . . . ? C9 C25 C30 C29 178.5(5) . . . . ? O2 C14 C31 C36 -17.1(7) . . . . ? C13a C14 C31 C36 97.0(6) . . . . ? C14a C14 C31 C36 -131.6(6) . . . . ? O2 C14 C31 C32 167.9(5) . . . . ? C13a C14 C31 C32 -78.0(6) . . . . ? C14a C14 C31 C32 53.5(7) . . . . ? C36 C31 C32 C33 -1.3(9) . . . . ? C14 C31 C32 C33 173.8(6) . . . . ? C31 C32 C33 C34 1.3(11) . . . . ? C32 C33 C34 C35 -0.7(13) . . . . ? C33 C34 C35 C36 0.2(13) . . . . ? C32 C31 C36 C35 0.8(10) . . . . ? C14 C31 C36 C35 -174.2(6) . . . . ? C34 C35 C36 C31 -0.2(12) . . . . ? O1 C17 C37 C42 -164.8(5) . . . . ? C17a C17 C37 C42 80.2(6) . . . . ? C16 C17 C37 C42 -46.9(6) . . . . ? O1 C17 C37 C38 18.1(6) . . . . ? C17a C17 C37 C38 -97.0(6) . . . . ? C16 C17 C37 C38 136.0(5) . . . . ? C42 C37 C38 C39 1.7(8) . . . . ? C17 C37 C38 C39 178.9(5) . . . . ? C37 C38 C39 C40 -1.8(9) . . . . ? C38 C39 C40 C41 0.8(11) . . . . ? C39 C40 C41 C42 0.1(11) . . . . ? C38 C37 C42 C41 -0.8(9) . . . . ? C17 C37 C42 C41 -178.0(6) . . . . ? C40 C41 C42 C37 -0.1(11) . . . . ? C48 C43 C44 C45 0.4(12) . . . . ? C43 C44 C45 C46 1.3(13) . . . . ? C44 C45 C46 C47 -1.6(15) . . . . ? C45 C46 C47 C48 0.1(15) . . . . ? C44 C43 C48 C47 -1.8(13) . . . . ? C46 C47 C48 C43 1.6(15) . . . . ? C54 C49 C50 C51 1(2) . . . . ? C49 C50 C51 C52 -1.4(19) . . . . ? C50 C51 C52 C53 1.2(19) . . . . ? C51 C52 C53 C54 -1(2) . . . . ? C50 C49 C54 C53 -1(2) . . . . ? C52 C53 C54 C49 1(2) . . . . ? data_13 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (5_a,6_b,9a_a,10_a,15_a,16_b,17_a)-15a-Bromo- 5,6,9a,10,15,15a,16,17-octahydro-5,17:10,15-diepoxy- 6,16-methanobenzo[5',6']cyclodeca[2',1'-3,4]cyclopenta [1,2-b]naphthaleno-9,18-dione ; _chemical_name_common ? _chemical_melting_point 195 _chemical_formula_moiety 'C26 H17 Br O4' _chemical_formula_sum 'C26 H17 Br O4' _chemical_formula_weight 473.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -.6763 1.2805 '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 1 21/n 1' 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 12.699(2) _cell_length_b 16.985(2) _cell_length_c 9.715(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.750(10) _cell_angle_gamma 90.00 _cell_volume 2051.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 22 _cell_measurement_theta_max 42 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 2.996 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.345 _exptl_absorpt_correction_T_max 0.407 _exptl_absorpt_process_details ; empirical via \y scans (North, Phillips, & Mathews, 1968). Relative values of T max and T min are 0.9998 and 0.8464, respectively. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius FR590' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0.5 _diffrn_reflns_number 3706 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 4.41 _diffrn_reflns_theta_max 64.95 _reflns_number_total 3487 _reflns_number_gt 3289 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CAD-4 Software (Enraf-Nonius, 1989) ; _computing_cell_refinement ; CAD-4 Software (Enraf-Nonius, 1989) ; _computing_data_reduction ; MolEN (Fair, 1990) ; _computing_structure_solution ; SIR92 (Altomare, Burla, Camalli, Cascarano, Giacovazzo, Guagliardi & Polidori, 1994) ; _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_molecular_graphics 'Xtal_GX (Hall & du Boulay, 1995)' _computing_publication_material 'SHELXL93 (Sheldrick, 1993)' _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^)+(0.0463P)^2^+1.8952P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3487 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.161 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max .231 _refine_diff_density_min -.809 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 0.98201(3) 0.111539(19) 0.19877(3) 0.04892(14) Uani 1 1 d . . . O1 O 1.00028(15) 0.10715(11) 0.6579(2) 0.0378(4) Uani 1 1 d . . . O2 O 0.93222(16) 0.28878(12) 0.06536(18) 0.0422(5) Uani 1 1 d . . . O3 O 1.17022(16) 0.33952(13) 0.4655(2) 0.0504(5) Uani 1 1 d . . . O4 O 0.72847(18) 0.23000(15) 0.5519(2) 0.0577(6) Uani 1 1 d . . . C1 C 0.7728(3) -0.0218(2) 0.5417(3) 0.0543(8) Uani 1 1 d . . . H1 H 0.7652 -0.0368 0.4482 0.065 Uiso 1 1 calc R . . C2 C 0.7127(3) -0.0579(2) 0.6294(4) 0.0633(10) Uani 1 1 d . . . H2 H 0.6651 -0.0981 0.5942 0.076 Uiso 1 1 calc R . . C3 C 0.7229(3) -0.0348(2) 0.7665(3) 0.0540(8) Uani 1 1 d . . . H3 H 0.6822 -0.0599 0.8230 0.065 Uiso 1 1 calc R . . C4 C 0.7924(2) 0.02499(17) 0.8226(3) 0.0425(6) Uani 1 1 d . . . H4 H 0.7978 0.0413 0.9152 0.051 Uiso 1 1 calc R . . C4a C 0.8534(2) 0.05949(16) 0.7372(3) 0.0353(6) Uani 1 1 d . . . C5 C 0.9372(2) 0.12317(17) 0.7626(3) 0.0373(6) Uani 1 1 d . . . H5 H 0.9809 0.1208 0.8581 0.045 Uiso 1 1 calc R . . C6 C 0.8862(2) 0.20614(16) 0.7280(3) 0.0396(6) Uani 1 1 d . . . H6 H 0.8396 0.2178 0.7943 0.048 Uiso 1 1 calc R . . C7 C 0.9735(3) 0.26671(18) 0.7451(3) 0.0457(7) Uani 1 1 d . . . H7 H 0.9899 0.2918 0.8319 0.055 Uiso 1 1 calc R . . C8 C 1.0304(2) 0.28891(17) 0.6507(3) 0.0408(6) Uani 1 1 d . . . H8 H 1.0848 0.3252 0.6822 0.049 Uiso 1 1 calc R . . C8a C 1.01915(19) 0.26409(15) 0.5046(3) 0.0311(5) Uani 1 1 d . . . C9 C 1.0936(2) 0.29787(16) 0.4205(3) 0.0349(6) Uani 1 1 d . . . C9a C 1.0587(2) 0.27114(17) 0.2703(3) 0.0350(6) Uani 1 1 d . . . H9a H 1.1164 0.2433 0.2372 0.042 Uiso 1 1 calc R . . C10 C 1.0067(2) 0.33610(18) 0.1646(3) 0.0394(6) Uani 1 1 d . . . H10 H 1.0576 0.3672 0.1235 0.047 Uiso 1 1 calc R . . C10a C 0.9307(2) 0.38389(16) 0.2334(3) 0.0365(6) Uani 1 1 d . . . C11 C 0.9353(3) 0.45699(19) 0.2964(3) 0.0503(7) Uani 1 1 d . . . H11 H 0.9944 0.4898 0.3000 0.060 Uiso 1 1 calc R . . C12 C 0.8487(3) 0.4799(2) 0.3543(4) 0.0570(8) Uani 1 1 d . . . H12 H 0.8494 0.5292 0.3960 0.068 Uiso 1 1 calc R . . C13 C 0.7619(3) 0.4308(2) 0.3510(3) 0.0524(8) Uani 1 1 d . . . H13 H 0.7044 0.4481 0.3890 0.063 Uiso 1 1 calc R . . C14 C 0.7584(2) 0.35630(18) 0.2924(3) 0.0403(6) Uani 1 1 d . . . H14 H 0.7008 0.3226 0.2931 0.048 Uiso 1 1 calc R . . C14a C 0.8440(2) 0.33403(16) 0.2328(2) 0.0332(6) Uani 1 1 d . . . C15 C 0.8707(2) 0.25911(16) 0.1647(3) 0.0337(6) Uani 1 1 d . . . H15 H 0.8089 0.2260 0.1244 0.040 Uiso 1 1 calc R . . C15a C 0.9618(2) 0.21722(15) 0.2721(2) 0.0303(5) Uani 1 1 d . . . C15b C 0.95005(19) 0.21434(15) 0.4235(2) 0.0281(5) Uani 1 1 d . . . C16 C 0.8683(2) 0.16254(15) 0.4690(2) 0.0296(5) Uani 1 1 d . . . H16 H 0.8118 0.1494 0.3875 0.036 Uiso 1 1 calc R . . C17 C 0.9222(2) 0.08496(16) 0.5365(3) 0.0349(6) Uani 1 1 d . . . H17 H 0.9544 0.0546 0.4698 0.042 Uiso 1 1 calc R . . C17a C 0.8432(2) 0.03633(16) 0.5974(3) 0.0376(6) Uani 1 1 d . . . C18 C 0.8180(2) 0.20362(16) 0.5806(3) 0.0345(6) 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 Br1 0.0707(3) 0.0445(2) 0.0353(2) -0.00610(12) 0.01951(15) 0.01366(14) O1 0.0364(10) 0.0444(11) 0.0323(10) 0.0035(8) 0.0067(8) 0.0015(8) O2 0.0516(11) 0.0560(12) 0.0206(9) 0.0051(8) 0.0111(8) 0.0065(9) O3 0.0408(11) 0.0602(14) 0.0468(12) 0.0105(10) 0.0011(9) -0.0142(10) O4 0.0477(12) 0.0784(16) 0.0539(13) 0.0154(12) 0.0266(10) 0.0231(11) C1 0.073(2) 0.0551(19) 0.0343(15) -0.0046(14) 0.0095(15) -0.0208(17) C2 0.074(2) 0.064(2) 0.0492(19) 0.0005(16) 0.0077(17) -0.0335(19) C3 0.0583(19) 0.058(2) 0.0492(18) 0.0091(15) 0.0192(15) -0.0122(15) C4 0.0541(17) 0.0419(15) 0.0349(14) 0.0035(12) 0.0172(13) 0.0000(13) C4a 0.0434(14) 0.0347(14) 0.0282(13) 0.0030(11) 0.0079(11) 0.0011(11) C5 0.0448(15) 0.0438(15) 0.0226(12) 0.0007(11) 0.0052(11) -0.0038(12) C6 0.0576(17) 0.0393(15) 0.0266(13) -0.0053(11) 0.0197(12) -0.0025(13) C7 0.073(2) 0.0418(16) 0.0245(13) -0.0097(12) 0.0149(13) -0.0113(14) C8 0.0540(16) 0.0402(15) 0.0269(13) -0.0035(11) 0.0052(12) -0.0123(13) C8a 0.0324(13) 0.0367(13) 0.0243(12) 0.0030(10) 0.0057(10) -0.0005(10) C9 0.0303(13) 0.0415(15) 0.0317(13) 0.0088(11) 0.0033(10) 0.0010(11) C9a 0.0305(13) 0.0484(16) 0.0285(13) 0.0036(11) 0.0118(10) 0.0046(11) C10 0.0403(14) 0.0502(16) 0.0304(13) 0.0081(12) 0.0132(11) 0.0010(12) C10a 0.0408(14) 0.0420(15) 0.0261(13) 0.0062(11) 0.0056(11) 0.0042(11) C11 0.0568(18) 0.0451(17) 0.0463(17) 0.0020(14) 0.0039(14) -0.0069(14) C12 0.076(2) 0.0476(18) 0.0465(18) -0.0126(14) 0.0097(16) 0.0071(17) C13 0.0553(18) 0.060(2) 0.0443(17) -0.0078(15) 0.0149(14) 0.0148(16) C14 0.0362(14) 0.0503(17) 0.0344(14) 0.0008(12) 0.0070(11) 0.0062(12) C14a 0.0363(13) 0.0393(14) 0.0223(12) 0.0029(10) 0.0021(10) 0.0062(11) C15 0.0355(13) 0.0439(15) 0.0212(12) 0.0009(10) 0.0047(10) 0.0029(11) C15a 0.0344(13) 0.0357(13) 0.0222(12) -0.0015(10) 0.0093(10) 0.0054(10) C15b 0.0295(12) 0.0348(13) 0.0209(11) 0.0016(10) 0.0071(9) 0.0058(10) C16 0.0325(12) 0.0364(13) 0.0206(11) -0.0020(10) 0.0068(9) -0.0011(10) C17 0.0438(14) 0.0347(13) 0.0275(12) -0.0031(11) 0.0106(11) 0.0013(11) C17a 0.0474(15) 0.0352(14) 0.0309(13) -0.0001(11) 0.0094(11) -0.0027(12) C18 0.0399(14) 0.0360(14) 0.0319(13) 0.0039(11) 0.0173(11) 0.0014(11) _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 Br11 C15a 1.967(3) . ? O1 C17 1.428(3) . ? O1 C5 1.443(3) . ? O2 C10 1.449(4) . ? O2 C15 1.451(3) . ? O3 C9 1.210(3) . ? O4 C18 1.201(3) . ? C1 C17a 1.367(4) . ? C1 C2 1.396(5) . ? C2 C3 1.368(5) . ? C3 C4 1.383(4) . ? C4 C4a 1.376(4) . ? C4a C17a 1.395(4) . ? C4a C5 1.502(4) . ? C5 C6 1.559(4) . ? C6 C7 1.496(4) . ? C6 C18 1.516(4) . ? C7 C8 1.333(4) . ? C8 C8a 1.459(4) . ? C8a C15b 1.350(4) . ? C8a C9 1.485(4) . ? C9 C9a 1.507(4) . ? C9a C15a 1.537(4) . ? C9a C10 1.559(4) . ? C10 C10a 1.517(4) . ? C10a C11 1.380(4) . ? C10a C14a 1.388(4) . ? C11 C12 1.388(5) . ? C12 C13 1.377(5) . ? C13 C14 1.385(5) . ? C14 C14a 1.385(4) . ? C14a C15 1.504(4) . ? C15 C15a 1.563(3) . ? C15a C15b 1.509(3) . ? C15b C16 1.495(3) . ? C16 C18 1.534(3) . ? C16 C17 1.566(4) . ? C17 C17a 1.510(4) . ? 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 C17 O1 C5 103.9(2) . . ? C10 O2 C15 96.75(18) . . ? C17a C1 C2 118.1(3) . . ? C3 C2 C1 120.9(3) . . ? C2 C3 C4 121.3(3) . . ? C4a C4 C3 117.9(3) . . ? C4 C4a C17a 121.0(3) . . ? C4 C4a C5 132.4(2) . . ? C17a C4a C5 106.5(2) . . ? O1 C5 C4a 103.0(2) . . ? O1 C5 C6 106.5(2) . . ? C4a C5 C6 111.5(2) . . ? C7 C6 C18 113.1(2) . . ? C7 C6 C5 109.4(2) . . ? C18 C6 C5 108.1(2) . . ? C8 C7 C6 127.7(3) . . ? C7 C8 C8a 128.9(3) . . ? C15b C8a C8 132.2(2) . . ? C15b C8a C9 109.4(2) . . ? C8 C8a C9 118.4(2) . . ? O3 C9 C8a 125.6(2) . . ? O3 C9 C9a 125.6(2) . . ? C8a C9 C9a 108.8(2) . . ? C9 C9a C15a 104.3(2) . . ? C9 C9a C10 115.2(2) . . ? C15a C9a C10 101.3(2) . . ? O2 C10 C10a 101.6(2) . . ? O2 C10 C9a 100.2(2) . . ? C10a C10 C9a 108.1(2) . . ? C11 C10a C14a 120.8(3) . . ? C11 C10a C10 134.7(3) . . ? C14a C10a C10 104.3(2) . . ? C10a C11 C12 117.8(3) . . ? C13 C12 C11 121.1(3) . . ? C12 C13 C14 121.4(3) . . ? C14a C14 C13 117.3(3) . . ? C14 C14a C10a 121.4(3) . . ? C14 C14a C15 132.9(3) . . ? C10a C14a C15 105.6(2) . . ? O2 C15 C14a 101.5(2) . . ? O2 C15 C15a 100.14(19) . . ? C14a C15 C15a 107.1(2) . . ? C15b C15a C9a 105.6(2) . . ? C15b C15a C15 117.3(2) . . ? C9a C15a C15 101.9(2) . . ? C15b C15a Br1 111.69(17) . . ? C9a C15a Br1 112.07(17) . . ? C15 C15a Br1 107.89(17) . . ? C8a C15b C16 127.1(2) . . ? C8a C15b C15a 111.5(2) . . ? C16 C15b C15a 121.3(2) . . ? C15b C16 C18 110.8(2) . . ? C15b C16 C17 110.4(2) . . ? C18 C16 C17 107.25(19) . . ? O1 C17 C17a 103.0(2) . . ? O1 C17 C16 107.1(2) . . ? C17a C17 C16 110.8(2) . . ? C1 C17a C4a 120.8(3) . . ? C1 C17a C17 132.3(3) . . ? C4a C17a C17 106.9(2) . . ? O4 C18 C6 122.7(2) . . ? O4 C18 C16 121.1(2) . . ? C6 C18 C16 116.1(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 C17a C1 C2 C3 1.0(6) . . . . ? C1 C2 C3 C4 0.3(6) . . . . ? C2 C3 C4 C4a -1.6(5) . . . . ? C3 C4 C4a C17a 1.7(4) . . . . ? C3 C4 C4a C5 -178.4(3) . . . . ? C17 O1 C5 C4a 39.6(2) . . . . ? C17 O1 C5 C6 -77.9(2) . . . . ? C4 C4a C5 O1 155.4(3) . . . . ? C17a C4a C5 O1 -24.6(3) . . . . ? C4 C4a C5 C6 -90.7(4) . . . . ? C17a C4a C5 C6 89.3(3) . . . . ? O1 C5 C6 C7 -64.4(3) . . . . ? C4a C5 C6 C7 -176.1(2) . . . . ? O1 C5 C6 C18 59.2(3) . . . . ? C4a C5 C6 C18 -52.5(3) . . . . ? C18 C6 C7 C8 -35.0(5) . . . . ? C5 C6 C7 C8 85.5(4) . . . . ? C6 C7 C8 C8a 4.0(6) . . . . ? C7 C8 C8a C15b 1.1(5) . . . . ? C7 C8 C8a C9 -179.9(3) . . . . ? C15b C8a C9 O3 -173.8(3) . . . . ? C8 C8a C9 O3 7.0(4) . . . . ? C15b C8a C9 C9a 5.7(3) . . . . ? C8 C8a C9 C9a -173.5(2) . . . . ? O3 C9 C9a C15a 177.5(3) . . . . ? C8a C9 C9a C15a -2.0(3) . . . . ? O3 C9 C9a C10 -72.4(3) . . . . ? C8a C9 C9a C10 108.2(3) . . . . ? C15 O2 C10 C10a -51.2(2) . . . . ? C15 O2 C10 C9a 59.8(2) . . . . ? C9 C9a C10 O2 -148.6(2) . . . . ? C15a C9a C10 O2 -36.7(2) . . . . ? C9 C9a C10 C10a -42.6(3) . . . . ? C15a C9a C10 C10a 69.2(3) . . . . ? O2 C10 C10a C11 -152.1(3) . . . . ? C9a C10 C10a C11 103.0(4) . . . . ? O2 C10 C10a C14a 32.4(3) . . . . ? C9a C10 C10a C14a -72.5(3) . . . . ? C14a C10a C11 C12 -2.3(4) . . . . ? C10 C10a C11 C12 -177.3(3) . . . . ? C10a C11 C12 C13 1.0(5) . . . . ? C11 C12 C13 C14 1.2(5) . . . . ? C12 C13 C14 C14a -2.2(5) . . . . ? C13 C14 C14a C10a 0.9(4) . . . . ? C13 C14 C14a C15 177.8(3) . . . . ? C11 C10a C14a C14 1.4(4) . . . . ? C10 C10a C14a C14 177.7(2) . . . . ? C11 C10a C14a C15 -176.2(2) . . . . ? C10 C10a C14a C15 0.0(3) . . . . ? C10 O2 C15 C14a 51.2(2) . . . . ? C10 O2 C15 C15a -58.8(2) . . . . ? C14 C14a C15 O2 150.4(3) . . . . ? C10a C14a C15 O2 -32.4(2) . . . . ? C14 C14a C15 C15a -105.1(3) . . . . ? C10a C14a C15 C15a 72.1(2) . . . . ? C9 C9a C15a C15b -1.9(3) . . . . ? C10 C9a C15a C15b -121.9(2) . . . . ? C9 C9a C15a C15 121.1(2) . . . . ? C10 C9a C15a C15 1.1(2) . . . . ? C9 C9a C15a Br1 -123.74(18) . . . . ? C10 C9a C15a Br1 116.27(19) . . . . ? O2 C15 C15a C15b 149.4(2) . . . . ? C14a C15 C15a C15b 43.9(3) . . . . ? O2 C15 C15a C9a 34.6(2) . . . . ? C14a C15 C15a C9a -70.8(2) . . . . ? O2 C15 C15a Br1 -83.51(19) . . . . ? C14a C15 C15a Br1 171.06(17) . . . . ? C8 C8a C15b C16 -6.7(5) . . . . ? C9 C8a C15b C16 174.2(2) . . . . ? C8 C8a C15b C15a 172.0(3) . . . . ? C9 C8a C15b C15a -7.1(3) . . . . ? C9a C15a C15b C8a 5.7(3) . . . . ? C15 C15a C15b C8a -107.0(3) . . . . ? Br1 C15a C15b C8a 127.8(2) . . . . ? C9a C15a C15b C16 -175.5(2) . . . . ? C15 C15a C15b C16 71.8(3) . . . . ? Br1 C15a C15b C16 -53.5(3) . . . . ? C8a C15b C16 C18 36.8(3) . . . . ? C15a C15b C16 C18 -141.8(2) . . . . ? C8a C15b C16 C17 -81.9(3) . . . . ? C15a C15b C16 C17 99.5(3) . . . . ? C5 O1 C17 C17a -38.9(2) . . . . ? C5 O1 C17 C16 78.0(2) . . . . ? C15b C16 C17 O1 62.0(2) . . . . ? C18 C16 C17 O1 -58.9(3) . . . . ? C15b C16 C17 C17a 173.7(2) . . . . ? C18 C16 C17 C17a 52.9(3) . . . . ? C2 C1 C17a C4a -0.9(5) . . . . ? C2 C1 C17a C17 177.5(3) . . . . ? C4 C4a C17a C1 -0.4(4) . . . . ? C5 C4a C17a C1 179.6(3) . . . . ? C4 C4a C17a C17 -179.2(3) . . . . ? C5 C4a C17a C17 0.8(3) . . . . ? O1 C17 C17a C1 -155.1(3) . . . . ? C16 C17 C17a C1 90.6(4) . . . . ? O1 C17 C17a C4a 23.5(3) . . . . ? C16 C17 C17a C4a -90.8(3) . . . . ? C7 C6 C18 O4 -105.1(3) . . . . ? C5 C6 C18 O4 133.6(3) . . . . ? C7 C6 C18 C16 76.9(3) . . . . ? C5 C6 C18 C16 -44.4(3) . . . . ? C15b C16 C18 O4 105.2(3) . . . . ? C17 C16 C18 O4 -134.2(3) . . . . ? C15b C16 C18 C6 -76.8(3) . . . . ? C17 C16 C18 C6 43.8(3) . . . . ?