# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12253 #TrackingRef '12253.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H18 Br N O3' _chemical_formula_sum 'C30 H18 Br N O3' _chemical_formula_weight 520.36 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 16.8022(2) _cell_length_b 14.5818(2) _cell_length_c 19.7887(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.4140(10) _cell_angle_gamma 90.00 _cell_volume 4839.75(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 37732 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2112 _exptl_absorpt_coefficient_mu 1.731 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4254 _exptl_absorpt_correction_T_max 0.474 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42574 _diffrn_reflns_av_R_equivalents 0.0818 _diffrn_reflns_av_sigmaI/netI 0.0624 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.02 _reflns_number_total 8519 _reflns_number_gt 5290 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1275P)^2^+20.1910P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8519 _refine_ls_number_parameters 631 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1141 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.2162 _refine_ls_wR_factor_gt 0.1638 _refine_ls_goodness_of_fit_ref 0.796 _refine_ls_restrained_S_all 0.796 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.60975(4) 0.18450(6) 0.33983(4) 0.0778(3) Uani 1 1 d . . . Br2 Br 0.86793(6) 0.47192(6) 0.16142(4) 0.0887(3) Uani 1 1 d . . . O1 O 0.7102(3) 0.3768(3) 0.0403(2) 0.0681(12) Uani 1 1 d . . . O2 O 0.6244(2) 0.4805(2) 0.07676(18) 0.0477(9) Uani 1 1 d . . . O3 O 0.8190(2) 0.6949(2) 0.15467(18) 0.0471(9) Uani 1 1 d . . . O4 O 0.7792(3) 0.2351(3) 0.4484(2) 0.0673(12) Uani 1 1 d . . . O5 O 0.8818(2) 0.1558(3) 0.40958(18) 0.0487(9) Uani 1 1 d . . . O6 O 0.6655(2) -0.0498(3) 0.35321(18) 0.0472(9) Uani 1 1 d . . . N1 N 0.5457(4) 0.6340(4) 0.1799(3) 0.0821(18) Uani 1 1 d . . . N2 N 0.9229(3) 0.0206(4) 0.2858(3) 0.0641(15) Uani 1 1 d . . . C1 C 0.6662(3) 0.4009(4) 0.0823(3) 0.0446(13) Uani 1 1 d . . . C2 C 0.6489(3) 0.3502(4) 0.1446(3) 0.0410(12) Uani 1 1 d . . . C3 C 0.6841(4) 0.2650(4) 0.1550(3) 0.0584(16) Uani 1 1 d . . . H3 H 0.7170 0.2416 0.1231 0.070 Uiso 1 1 calc R . . C4 C 0.6708(4) 0.2144(4) 0.2122(3) 0.0637(17) Uani 1 1 d . . . H4 H 0.6938 0.1569 0.2189 0.076 Uiso 1 1 calc R . . C5 C 0.6227(3) 0.2515(4) 0.2587(3) 0.0477(14) Uani 1 1 d . . . C6 C 0.5873(3) 0.3351(4) 0.2497(3) 0.0463(13) Uani 1 1 d . . . H6 H 0.5546 0.3582 0.2819 0.056 Uiso 1 1 calc R . . C7 C 0.6005(3) 0.3846(4) 0.1927(3) 0.0422(12) Uani 1 1 d . . . H7 H 0.5767 0.4418 0.1862 0.051 Uiso 1 1 calc R . . C8 C 0.6304(3) 0.5328(4) 0.0177(3) 0.0429(13) Uani 1 1 d . . . C9 C 0.5895(3) 0.5063(4) -0.0417(3) 0.0526(15) Uani 1 1 d . . . H9 H 0.5601 0.4522 -0.0432 0.063 Uiso 1 1 calc R . . C10 C 0.5925(3) 0.5601(5) -0.0988(3) 0.0588(17) Uani 1 1 d . . . H10 H 0.5659 0.5419 -0.1392 0.071 Uiso 1 1 calc R . . C11 C 0.6347(4) 0.6404(5) -0.0957(3) 0.0573(16) Uani 1 1 d . . . H11 H 0.6368 0.6768 -0.1342 0.069 Uiso 1 1 calc R . . C12 C 0.6742(3) 0.6679(4) -0.0361(3) 0.0495(14) Uani 1 1 d . . . H12 H 0.7015 0.7234 -0.0346 0.059 Uiso 1 1 calc R . . C13 C 0.6739(3) 0.6135(4) 0.0224(2) 0.0379(12) Uani 1 1 d . . . C14 C 0.7202(3) 0.6425(4) 0.0844(2) 0.0391(12) Uani 1 1 d . . . C15 C 0.7977(3) 0.6674(3) 0.0896(2) 0.0380(12) Uani 1 1 d . . . C16 C 0.8627(3) 0.6704(4) 0.0435(3) 0.0405(12) Uani 1 1 d . . . C17 C 0.8691(4) 0.6049(4) -0.0068(3) 0.0568(16) Uani 1 1 d . . . H17 H 0.8315 0.5582 -0.0119 0.068 Uiso 1 1 calc R . . C18 C 0.9311(4) 0.6091(5) -0.0490(3) 0.0678(18) Uani 1 1 d . . . H18 H 0.9348 0.5655 -0.0830 0.081 Uiso 1 1 calc R . . C19 C 0.9869(4) 0.6763(5) -0.0417(3) 0.0661(18) Uani 1 1 d . . . H19 H 1.0286 0.6783 -0.0705 0.079 Uiso 1 1 calc R . . C20 C 0.9822(4) 0.7408(5) 0.0077(3) 0.0638(17) Uani 1 1 d . . . H20 H 1.0205 0.7868 0.0123 0.077 Uiso 1 1 calc R . . C21 C 0.9204(3) 0.7381(4) 0.0512(3) 0.0505(14) Uani 1 1 d . . . H21 H 0.9178 0.7816 0.0854 0.061 Uiso 1 1 calc R . . C22 C 0.6918(3) 0.6546(4) 0.1518(3) 0.0452(13) Uani 1 1 d . . . C23 C 0.6115(4) 0.6429(4) 0.1690(3) 0.0547(15) Uani 1 1 d . . . C24 C 0.7545(4) 0.6861(4) 0.1927(3) 0.0469(14) Uani 1 1 d . . . C25 C 0.7683(4) 0.7092(4) 0.2638(3) 0.0567(16) Uani 1 1 d . . . C26 C 0.8400(5) 0.7476(5) 0.2871(3) 0.071(2) Uani 1 1 d . . . H26 H 0.8795 0.7588 0.2571 0.085 Uiso 1 1 calc R . . C27 C 0.8530(6) 0.7694(5) 0.3551(4) 0.090(3) Uani 1 1 d . . . H27 H 0.9012 0.7953 0.3708 0.109 Uiso 1 1 calc R . . C28 C 0.7950(7) 0.7526(5) 0.3989(3) 0.089(3) Uani 1 1 d . . . H28 H 0.8040 0.7669 0.4446 0.106 Uiso 1 1 calc R . . C29 C 0.7243(6) 0.7152(6) 0.3765(4) 0.086(2) Uani 1 1 d . . . H29 H 0.6850 0.7044 0.4068 0.103 Uiso 1 1 calc R . . C30 C 0.7105(5) 0.6932(5) 0.3098(3) 0.072(2) Uani 1 1 d . . . H30 H 0.6620 0.6672 0.2950 0.087 Uiso 1 1 calc R . . C31 C 0.8262(3) 0.2237(4) 0.4061(3) 0.0452(13) Uani 1 1 d . . . C32 C 0.8335(3) 0.2806(4) 0.3447(3) 0.0415(12) Uani 1 1 d . . . C33 C 0.7856(3) 0.3565(4) 0.3337(3) 0.0505(14) Uani 1 1 d . . . H33 H 0.7461 0.3691 0.3634 0.061 Uiso 1 1 calc R . . C34 C 0.7951(4) 0.4136(4) 0.2800(3) 0.0564(15) Uani 1 1 d . . . H34 H 0.7629 0.4651 0.2732 0.068 Uiso 1 1 calc R . . C35 C 0.8531(4) 0.3933(4) 0.2362(3) 0.0521(14) Uani 1 1 d . . . C36 C 0.9010(4) 0.3177(4) 0.2444(3) 0.0540(15) Uani 1 1 d . . . H36 H 0.9390 0.3046 0.2136 0.065 Uiso 1 1 calc R . . C37 C 0.8916(3) 0.2617(4) 0.2993(3) 0.0493(14) Uani 1 1 d . . . H37 H 0.9244 0.2107 0.3062 0.059 Uiso 1 1 calc R . . C38 C 0.8844(3) 0.0975(4) 0.4659(3) 0.0465(13) Uani 1 1 d . . . C39 C 0.9401(4) 0.1164(5) 0.5186(3) 0.0613(17) Uani 1 1 d . . . H39 H 0.9724 0.1680 0.5172 0.074 Uiso 1 1 calc R . . C40 C 0.9467(4) 0.0578(6) 0.5727(3) 0.075(2) Uani 1 1 d . . . H40 H 0.9827 0.0702 0.6090 0.090 Uiso 1 1 calc R . . C41 C 0.8999(4) -0.0193(5) 0.5733(3) 0.0662(18) Uani 1 1 d . . . H41 H 0.9053 -0.0595 0.6098 0.079 Uiso 1 1 calc R . . C42 C 0.8454(3) -0.0381(4) 0.5206(3) 0.0536(15) Uani 1 1 d . . . H42 H 0.8141 -0.0906 0.5220 0.064 Uiso 1 1 calc R . . C43 C 0.8365(3) 0.0207(4) 0.4653(3) 0.0417(12) Uani 1 1 d . . . C44 C 0.7775(3) -0.0003(4) 0.4093(3) 0.0423(13) Uani 1 1 d . . . C45 C 0.7001(3) -0.0263(4) 0.4159(3) 0.0436(13) Uani 1 1 d . . . C46 C 0.6494(3) -0.0318(4) 0.4729(3) 0.0466(14) Uani 1 1 d . . . C47 C 0.6569(3) 0.0330(4) 0.5244(3) 0.0531(15) Uani 1 1 d . . . H47 H 0.6936 0.0805 0.5219 0.064 Uiso 1 1 calc R . . C48 C 0.6103(4) 0.0270(5) 0.5791(3) 0.0633(17) Uani 1 1 d . . . H48 H 0.6167 0.0697 0.6139 0.076 Uiso 1 1 calc R . . C49 C 0.5545(4) -0.0411(5) 0.5828(3) 0.0657(19) Uani 1 1 d . . . H49 H 0.5227 -0.0438 0.6197 0.079 Uiso 1 1 calc R . . C50 C 0.5454(4) -0.1060(5) 0.5315(4) 0.0641(18) Uani 1 1 d . . . H50 H 0.5076 -0.1523 0.5338 0.077 Uiso 1 1 calc R . . C51 C 0.5932(3) -0.1013(4) 0.4769(3) 0.0547(15) Uani 1 1 d . . . H51 H 0.5876 -0.1449 0.4427 0.066 Uiso 1 1 calc R . . C52 C 0.7902(3) -0.0090(4) 0.3382(3) 0.0428(13) Uani 1 1 d . . . C53 C 0.8635(4) 0.0081(4) 0.3082(3) 0.0461(13) Uani 1 1 d . . . C54 C 0.7208(3) -0.0395(4) 0.3059(3) 0.0450(13) Uani 1 1 d . . . C55 C 0.6958(4) -0.0634(4) 0.2366(3) 0.0485(14) Uani 1 1 d . . . C56 C 0.6175(4) -0.0887(5) 0.2203(3) 0.0653(18) Uani 1 1 d . . . H56 H 0.5807 -0.0886 0.2536 0.078 Uiso 1 1 calc R . . C57 C 0.5937(5) -0.1141(5) 0.1550(4) 0.073(2) Uani 1 1 d . . . H57 H 0.5411 -0.1311 0.1446 0.088 Uiso 1 1 calc R . . C58 C 0.6470(5) -0.1145(5) 0.1056(3) 0.0676(19) Uani 1 1 d . . . H58 H 0.6311 -0.1326 0.0618 0.081 Uiso 1 1 calc R . . C59 C 0.7236(5) -0.0883(5) 0.1210(3) 0.0684(19) Uani 1 1 d . . . H59 H 0.7597 -0.0873 0.0871 0.082 Uiso 1 1 calc R . . C60 C 0.7486(4) -0.0631(5) 0.1860(3) 0.0620(17) Uani 1 1 d . . . H60 H 0.8014 -0.0459 0.1957 0.074 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 0.0697(5) 0.0890(6) 0.0749(5) 0.0419(4) 0.0048(4) -0.0036(4) Br2 0.1084(7) 0.0762(5) 0.0824(5) 0.0371(4) 0.0130(5) 0.0175(5) O1 0.080(3) 0.076(3) 0.051(2) 0.009(2) 0.020(2) 0.024(3) O2 0.056(2) 0.042(2) 0.047(2) 0.0084(17) 0.0135(18) -0.0007(18) O3 0.056(2) 0.046(2) 0.040(2) -0.0023(17) 0.0054(17) -0.0038(18) O4 0.062(3) 0.093(3) 0.049(2) 0.006(2) 0.015(2) 0.012(2) O5 0.050(2) 0.050(2) 0.047(2) 0.0098(18) 0.0050(17) -0.0014(19) O6 0.044(2) 0.054(2) 0.042(2) 0.0040(17) -0.0022(17) -0.0051(18) N1 0.069(4) 0.085(4) 0.096(5) 0.015(4) 0.036(4) 0.001(3) N2 0.059(4) 0.085(4) 0.050(3) -0.002(3) 0.015(3) -0.012(3) C1 0.043(3) 0.049(3) 0.041(3) -0.003(3) -0.001(2) 0.000(3) C2 0.040(3) 0.042(3) 0.040(3) 0.002(2) -0.001(2) -0.004(2) C3 0.071(4) 0.049(4) 0.057(4) 0.005(3) 0.016(3) 0.011(3) C4 0.076(5) 0.044(4) 0.071(4) 0.008(3) 0.007(4) 0.011(3) C5 0.044(3) 0.048(3) 0.051(3) 0.010(3) 0.000(3) -0.007(3) C6 0.042(3) 0.047(3) 0.051(3) 0.005(3) 0.008(2) -0.004(3) C7 0.037(3) 0.043(3) 0.046(3) 0.003(2) 0.003(2) -0.001(2) C8 0.043(3) 0.047(3) 0.039(3) 0.005(2) 0.007(2) 0.005(3) C9 0.041(3) 0.060(4) 0.057(4) -0.006(3) 0.007(3) -0.007(3) C10 0.044(3) 0.094(5) 0.039(3) 0.009(3) -0.003(3) 0.006(3) C11 0.054(4) 0.075(4) 0.044(3) 0.019(3) 0.003(3) 0.010(3) C12 0.047(3) 0.049(3) 0.053(3) 0.014(3) 0.010(3) 0.008(3) C13 0.034(3) 0.042(3) 0.039(3) 0.007(2) 0.008(2) 0.001(2) C14 0.037(3) 0.040(3) 0.041(3) 0.008(2) 0.005(2) 0.003(2) C15 0.043(3) 0.034(3) 0.037(3) 0.000(2) 0.003(2) 0.003(2) C16 0.037(3) 0.045(3) 0.039(3) 0.008(2) 0.002(2) 0.005(2) C17 0.052(4) 0.065(4) 0.055(4) -0.009(3) 0.014(3) -0.012(3) C18 0.070(4) 0.071(5) 0.063(4) -0.020(3) 0.020(3) -0.010(4) C19 0.059(4) 0.078(5) 0.064(4) -0.004(4) 0.024(3) -0.003(4) C20 0.041(3) 0.070(4) 0.081(5) -0.003(4) 0.012(3) -0.014(3) C21 0.044(3) 0.051(4) 0.057(3) 0.000(3) 0.002(3) -0.004(3) C22 0.055(4) 0.039(3) 0.043(3) 0.007(2) 0.017(3) 0.005(3) C23 0.071(5) 0.045(3) 0.050(3) 0.003(3) 0.020(3) 0.008(3) C24 0.060(4) 0.039(3) 0.042(3) 0.003(2) 0.008(3) 0.001(3) C25 0.091(5) 0.041(3) 0.039(3) 0.004(3) 0.012(3) 0.008(3) C26 0.106(6) 0.057(4) 0.048(4) 0.001(3) 0.000(4) -0.009(4) C27 0.148(8) 0.070(5) 0.052(4) -0.004(4) -0.006(5) -0.019(5) C28 0.170(9) 0.058(5) 0.038(4) -0.006(3) 0.007(5) 0.011(5) C29 0.133(8) 0.077(5) 0.050(4) 0.003(4) 0.026(5) 0.016(5) C30 0.102(6) 0.073(5) 0.043(4) 0.001(3) 0.016(4) 0.010(4) C31 0.045(3) 0.050(3) 0.040(3) -0.003(3) -0.005(3) -0.008(3) C32 0.034(3) 0.048(3) 0.042(3) -0.006(2) -0.007(2) -0.003(2) C33 0.046(3) 0.053(4) 0.051(3) -0.007(3) 0.001(3) 0.009(3) C34 0.056(4) 0.050(4) 0.062(4) 0.002(3) -0.001(3) 0.016(3) C35 0.051(4) 0.053(4) 0.051(3) 0.004(3) -0.004(3) 0.002(3) C36 0.053(4) 0.052(4) 0.057(4) 0.007(3) 0.007(3) 0.007(3) C37 0.049(3) 0.046(3) 0.053(3) 0.004(3) 0.006(3) 0.010(3) C38 0.042(3) 0.056(4) 0.041(3) 0.007(3) 0.003(2) -0.001(3) C39 0.056(4) 0.067(4) 0.060(4) -0.001(3) -0.009(3) -0.011(3) C40 0.070(5) 0.098(6) 0.053(4) 0.009(4) -0.025(3) -0.005(4) C41 0.069(4) 0.079(5) 0.050(4) 0.018(3) -0.007(3) 0.011(4) C42 0.047(3) 0.065(4) 0.049(3) 0.014(3) 0.001(3) 0.000(3) C43 0.039(3) 0.049(3) 0.037(3) 0.010(2) 0.001(2) -0.003(3) C44 0.042(3) 0.045(3) 0.039(3) 0.009(2) -0.003(2) 0.001(2) C45 0.043(3) 0.045(3) 0.042(3) 0.004(2) -0.002(2) -0.001(3) C46 0.041(3) 0.053(4) 0.046(3) 0.014(3) 0.000(2) 0.001(3) C47 0.045(3) 0.066(4) 0.049(3) 0.002(3) 0.007(3) -0.006(3) C48 0.058(4) 0.082(5) 0.050(4) 0.005(3) 0.008(3) 0.001(4) C49 0.056(4) 0.083(5) 0.060(4) 0.025(4) 0.017(3) 0.021(4) C50 0.042(3) 0.067(4) 0.084(5) 0.031(4) 0.013(3) 0.002(3) C51 0.050(4) 0.050(4) 0.064(4) 0.019(3) 0.004(3) 0.000(3) C52 0.046(3) 0.046(3) 0.036(3) 0.007(2) 0.002(2) 0.002(3) C53 0.048(4) 0.050(3) 0.040(3) 0.003(3) 0.001(3) -0.001(3) C54 0.046(3) 0.047(3) 0.042(3) 0.007(2) 0.002(3) -0.001(3) C55 0.057(4) 0.039(3) 0.047(3) 0.004(3) -0.010(3) -0.005(3) C56 0.068(4) 0.070(5) 0.057(4) -0.005(3) -0.006(3) 0.001(4) C57 0.077(5) 0.074(5) 0.066(5) -0.005(4) -0.022(4) -0.005(4) C58 0.094(6) 0.058(4) 0.048(4) -0.001(3) -0.022(4) -0.004(4) C59 0.091(5) 0.070(5) 0.044(4) 0.005(3) 0.005(3) -0.006(4) C60 0.073(4) 0.071(4) 0.041(3) 0.006(3) -0.001(3) -0.012(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C5 1.903(5) . ? Br2 C35 1.900(6) . ? O1 C1 1.196(6) . ? O2 C1 1.359(7) . ? O2 C8 1.404(6) . ? O3 C15 1.375(6) . ? O3 C24 1.362(7) . ? O4 C31 1.198(7) . ? O5 C31 1.360(7) . ? O5 C38 1.399(6) . ? O6 C54 1.366(6) . ? O6 C45 1.381(6) . ? N1 C23 1.146(8) . ? N2 C53 1.132(7) . ? C1 C2 1.481(7) . ? C2 C7 1.382(7) . ? C2 C3 1.386(8) . ? C3 C4 1.379(8) . ? C3 H3 0.9300 . ? C4 C5 1.373(8) . ? C4 H4 0.9300 . ? C5 C6 1.363(8) . ? C6 C7 1.369(7) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C13 1.386(7) . ? C8 C9 1.380(8) . ? C9 C10 1.380(8) . ? C9 H9 0.9300 . ? C10 C11 1.369(9) . ? C10 H10 0.9300 . ? C11 C12 1.378(8) . ? C11 H11 0.9300 . ? C12 C13 1.404(7) . ? C12 H12 0.9300 . ? C13 C14 1.474(7) . ? C14 C15 1.351(7) . ? C14 C22 1.453(7) . ? C15 C16 1.465(7) . ? C16 C17 1.388(8) . ? C16 C21 1.387(8) . ? C17 C18 1.375(8) . ? C17 H17 0.9300 . ? C18 C19 1.359(9) . ? C18 H18 0.9300 . ? C19 C20 1.363(9) . ? C19 H19 0.9300 . ? C20 C21 1.387(8) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C24 1.368(8) . ? C22 C23 1.421(9) . ? C24 C25 1.453(8) . ? C25 C26 1.382(10) . ? C25 C30 1.389(9) . ? C26 C27 1.388(9) . ? C26 H26 0.9300 . ? C27 C28 1.366(12) . ? C27 H27 0.9300 . ? C28 C29 1.357(12) . ? C28 H28 0.9300 . ? C29 C30 1.365(10) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 C32 1.483(8) . ? C32 C37 1.393(8) . ? C32 C33 1.378(8) . ? C33 C34 1.367(8) . ? C33 H33 0.9300 . ? C34 C35 1.374(8) . ? C34 H34 0.9300 . ? C35 C36 1.369(8) . ? C36 C37 1.376(8) . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? C38 C43 1.380(8) . ? C38 C39 1.386(8) . ? C39 C40 1.370(9) . ? C39 H39 0.9300 . ? C40 C41 1.372(10) . ? C40 H40 0.9300 . ? C41 C42 1.374(9) . ? C41 H41 0.9300 . ? C42 C43 1.392(7) . ? C42 H42 0.9300 . ? C43 C44 1.473(7) . ? C44 C45 1.369(7) . ? C44 C52 1.442(7) . ? C45 C46 1.456(8) . ? C46 C47 1.390(8) . ? C46 C51 1.390(8) . ? C47 C48 1.376(8) . ? C47 H47 0.9300 . ? C48 C49 1.371(10) . ? C48 H48 0.9300 . ? C49 C50 1.390(10) . ? C49 H49 0.9300 . ? C50 C51 1.386(9) . ? C50 H50 0.9300 . ? C51 H51 0.9300 . ? C52 C54 1.371(8) . ? C52 C53 1.420(8) . ? C54 C55 1.452(8) . ? C55 C60 1.377(8) . ? C55 C56 1.386(9) . ? C56 C57 1.380(9) . ? C56 H56 0.9300 . ? C57 C58 1.364(10) . ? C57 H57 0.9300 . ? C58 C59 1.359(10) . ? C58 H58 0.9300 . ? C59 C60 1.380(9) . ? C59 H59 0.9300 . ? C60 H60 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C8 118.0(4) . . ? C15 O3 C24 108.6(4) . . ? C31 O5 C38 118.1(4) . . ? C54 O6 C45 108.8(4) . . ? O1 C1 O2 122.2(5) . . ? O1 C1 C2 126.3(5) . . ? O2 C1 C2 111.5(5) . . ? C7 C2 C3 119.1(5) . . ? C7 C2 C1 123.0(5) . . ? C3 C2 C1 117.9(5) . . ? C2 C3 C4 120.9(6) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 118.0(6) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? C4 C5 C6 122.3(5) . . ? C4 C5 Br1 117.7(4) . . ? C6 C5 Br1 119.9(4) . . ? C5 C6 C7 119.3(5) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C2 C7 C6 120.4(5) . . ? C2 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C13 C8 C9 122.0(5) . . ? C13 C8 O2 117.9(5) . . ? C9 C8 O2 120.0(5) . . ? C8 C9 C10 119.8(6) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 119.6(6) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.6(5) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C13 121.1(6) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C8 C13 C12 116.8(5) . . ? C8 C13 C14 123.3(4) . . ? C12 C13 C14 119.8(5) . . ? C15 C14 C22 105.3(5) . . ? C15 C14 C13 126.8(5) . . ? C22 C14 C13 127.8(5) . . ? O3 C15 C14 110.2(4) . . ? O3 C15 C16 114.4(4) . . ? C14 C15 C16 135.4(5) . . ? C17 C16 C21 119.1(5) . . ? C17 C16 C15 121.3(5) . . ? C21 C16 C15 119.6(5) . . ? C16 C17 C18 119.9(6) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 120.7(6) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C20 C19 C18 120.3(6) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C21 120.2(6) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C16 C21 C20 119.7(6) . . ? C16 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C24 C22 C23 127.3(5) . . ? C24 C22 C14 107.5(5) . . ? C23 C22 C14 124.9(5) . . ? N1 C23 C22 177.1(7) . . ? C22 C24 O3 108.3(5) . . ? C22 C24 C25 136.4(6) . . ? O3 C24 C25 115.3(5) . . ? C26 C25 C30 118.7(6) . . ? C26 C25 C24 120.2(6) . . ? C30 C25 C24 121.2(6) . . ? C25 C26 C27 120.0(7) . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 120.0 . . ? C28 C27 C26 119.9(8) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C29 C28 C27 120.6(7) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C28 C29 C30 120.3(8) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? C29 C30 C25 120.6(8) . . ? C29 C30 H30 119.7 . . ? C25 C30 H30 119.7 . . ? O4 C31 O5 123.1(5) . . ? O4 C31 C32 125.8(6) . . ? O5 C31 C32 111.1(5) . . ? C37 C32 C33 118.9(5) . . ? C37 C32 C31 120.8(5) . . ? C33 C32 C31 120.2(5) . . ? C34 C33 C32 121.1(5) . . ? C34 C33 H33 119.5 . . ? C32 C33 H33 119.5 . . ? C35 C34 C33 118.7(5) . . ? C35 C34 H34 120.7 . . ? C33 C34 H34 120.7 . . ? C34 C35 C36 122.1(6) . . ? C34 C35 Br2 119.5(5) . . ? C36 C35 Br2 118.4(5) . . ? C37 C36 C35 118.6(6) . . ? C37 C36 H36 120.7 . . ? C35 C36 H36 120.7 . . ? C32 C37 C36 120.5(5) . . ? C32 C37 H37 119.7 . . ? C36 C37 H37 119.7 . . ? C43 C38 C39 122.3(5) . . ? C43 C38 O5 119.7(5) . . ? C39 C38 O5 117.8(5) . . ? C38 C39 C40 119.0(6) . . ? C38 C39 H39 120.5 . . ? C40 C39 H39 120.5 . . ? C41 C40 C39 119.9(6) . . ? C41 C40 H40 120.0 . . ? C39 C40 H40 120.0 . . ? C40 C41 C42 120.9(6) . . ? C40 C41 H41 119.6 . . ? C42 C41 H41 119.6 . . ? C41 C42 C43 120.6(6) . . ? C41 C42 H42 119.7 . . ? C43 C42 H42 119.7 . . ? C38 C43 C42 117.3(5) . . ? C38 C43 C44 122.7(5) . . ? C42 C43 C44 120.0(5) . . ? C45 C44 C52 105.3(5) . . ? C45 C44 C43 125.9(5) . . ? C52 C44 C43 128.4(5) . . ? O6 C45 C44 109.6(5) . . ? O6 C45 C46 116.6(5) . . ? C44 C45 C46 133.8(5) . . ? C47 C46 C51 119.1(5) . . ? C47 C46 C45 119.9(5) . . ? C51 C46 C45 121.0(5) . . ? C46 C47 C48 120.1(6) . . ? C46 C47 H47 119.9 . . ? C48 C47 H47 119.9 . . ? C49 C48 C47 120.8(7) . . ? C49 C48 H48 119.6 . . ? C47 C48 H48 119.6 . . ? C48 C49 C50 120.0(6) . . ? C48 C49 H49 120.0 . . ? C50 C49 H49 120.0 . . ? C49 C50 C51 119.4(6) . . ? C49 C50 H50 120.3 . . ? C51 C50 H50 120.3 . . ? C50 C51 C46 120.6(6) . . ? C50 C51 H51 119.7 . . ? C46 C51 H51 119.7 . . ? C54 C52 C53 126.7(5) . . ? C54 C52 C44 108.2(5) . . ? C53 C52 C44 125.1(5) . . ? N2 C53 C52 178.1(6) . . ? O6 C54 C52 108.1(4) . . ? O6 C54 C55 116.8(5) . . ? C52 C54 C55 135.1(5) . . ? C60 C55 C56 118.4(6) . . ? C60 C55 C54 121.6(5) . . ? C56 C55 C54 120.1(6) . . ? C57 C56 C55 120.5(7) . . ? C57 C56 H56 119.8 . . ? C55 C56 H56 119.8 . . ? C58 C57 C56 120.4(7) . . ? C58 C57 H57 119.8 . . ? C56 C57 H57 119.8 . . ? C57 C58 C59 119.4(6) . . ? C57 C58 H58 120.3 . . ? C59 C58 H58 120.3 . . ? C58 C59 C60 121.0(7) . . ? C58 C59 H59 119.5 . . ? C60 C59 H59 119.5 . . ? C55 C60 C59 120.3(6) . . ? C55 C60 H60 119.9 . . ? C59 C60 H60 119.9 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.413 _refine_diff_density_min -0.617 _refine_diff_density_rms 0.135 _database_code_depnum_ccdc_archive 'CCDC 881548' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12405 #TrackingRef '12405.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H42 Br Cl3 N O3 P' _chemical_formula_sum 'C36 H42 Br Cl3 N O3 P' _chemical_formula_weight 753.94 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' Br Br -0.2901 2.4595 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8458(2) _cell_length_b 27.2982(6) _cell_length_c 15.4284(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.0790(10) _cell_angle_gamma 90.00 _cell_volume 3723.11(14) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 16919 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 1.397 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6924 _exptl_absorpt_correction_T_max 0.8155 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22157 _diffrn_reflns_av_R_equivalents 0.0961 _diffrn_reflns_av_sigmaI/netI 0.0938 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 24.99 _reflns_number_total 6519 _reflns_number_gt 3953 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1204P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6519 _refine_ls_number_parameters 404 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1318 _refine_ls_R_factor_gt 0.0712 _refine_ls_wR_factor_ref 0.2346 _refine_ls_wR_factor_gt 0.1846 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7544(7) 0.1609(2) 0.1552(4) 0.0387(15) Uani 1 1 d . . . C2 C 0.7502(6) 0.1164(2) 0.0992(4) 0.0314(14) Uani 1 1 d . . . C3 C 0.8341(7) 0.1175(2) 0.0246(4) 0.0446(17) Uani 1 1 d . . . H3 H 0.8873 0.1464 0.0101 0.054 Uiso 1 1 calc R . . C4 C 0.8407(7) 0.0771(2) -0.0284(4) 0.0459(17) Uani 1 1 d . . . H4 H 0.8996 0.0779 -0.0787 0.055 Uiso 1 1 calc R . . C5 C 0.7614(7) 0.0355(2) -0.0080(4) 0.0378(15) Uani 1 1 d . . . C6 C 0.6722(8) 0.0341(2) 0.0646(4) 0.0449(16) Uani 1 1 d . . . H6 H 0.6144 0.0058 0.0771 0.054 Uiso 1 1 calc R . . C7 C 0.6694(7) 0.0744(2) 0.1175(4) 0.0422(16) Uani 1 1 d . . . H7 H 0.6107 0.0735 0.1678 0.051 Uiso 1 1 calc R . . C8 C 0.6800(6) 0.1906(2) 0.2913(4) 0.0329(14) Uani 1 1 d . . . C9 C 0.8064(7) 0.2035(3) 0.3408(4) 0.0476(18) Uani 1 1 d . . . H9 H 0.8994 0.1868 0.3338 0.057 Uiso 1 1 calc R . . C10 C 0.7973(7) 0.2405(3) 0.4005(4) 0.0462(18) Uani 1 1 d . . . H10 H 0.8838 0.2494 0.4353 0.055 Uiso 1 1 calc R . . C11 C 0.6628(7) 0.2649(2) 0.4098(4) 0.0419(16) Uani 1 1 d . . . H11 H 0.6562 0.2909 0.4504 0.050 Uiso 1 1 calc R . . C12 C 0.5363(6) 0.2511(2) 0.3591(4) 0.0350(15) Uani 1 1 d . . . H12 H 0.4438 0.2682 0.3652 0.042 Uiso 1 1 calc R . . C13 C 0.5425(6) 0.2128(2) 0.2999(3) 0.0267(13) Uani 1 1 d . . . C14 C 0.4034(6) 0.1937(2) 0.2489(3) 0.0258(12) Uani 1 1 d . . . H14 H 0.4427 0.1662 0.2133 0.031 Uiso 1 1 calc R . . C15 C 0.2175(6) 0.1979(2) 0.0912(3) 0.0315(14) Uani 1 1 d . . . H15A H 0.1513 0.1751 0.1222 0.038 Uiso 1 1 calc R . . H15B H 0.1517 0.2189 0.0536 0.038 Uiso 1 1 calc R . . C16 C 0.3213(7) 0.1680(2) 0.0338(4) 0.0380(15) Uani 1 1 d . . . H16A H 0.3987 0.1901 0.0103 0.046 Uiso 1 1 calc R . . H16B H 0.3746 0.1430 0.0700 0.046 Uiso 1 1 calc R . . C17 C 0.2389(8) 0.1429(2) -0.0403(4) 0.0477(18) Uani 1 1 d . . . H17A H 0.1837 0.1677 -0.0761 0.057 Uiso 1 1 calc R . . H17B H 0.1635 0.1200 -0.0172 0.057 Uiso 1 1 calc R . . C18 C 0.3458(9) 0.1147(3) -0.0971(5) 0.062(2) Uani 1 1 d . . . H18A H 0.2878 0.0989 -0.1446 0.094 Uiso 1 1 calc R . . H18B H 0.3991 0.0897 -0.0622 0.094 Uiso 1 1 calc R . . H18C H 0.4195 0.1374 -0.1209 0.094 Uiso 1 1 calc R . . C20 C 0.4556(7) 0.2701(2) 0.1110(4) 0.0382(15) Uani 1 1 d . . . H20A H 0.5423 0.2482 0.1009 0.046 Uiso 1 1 calc R . . H20B H 0.4101 0.2788 0.0535 0.046 Uiso 1 1 calc R . . C21 C 0.5164(8) 0.3168(2) 0.1533(4) 0.0471(17) Uani 1 1 d . . . H21A H 0.5689 0.3086 0.2092 0.057 Uiso 1 1 calc R . . H21B H 0.4311 0.3389 0.1654 0.057 Uiso 1 1 calc R . . C22 C 0.6271(8) 0.3431(3) 0.0941(5) 0.056(2) Uani 1 1 d . . . H22A H 0.6821 0.3684 0.1287 0.067 Uiso 1 1 calc R . . H22B H 0.7027 0.3190 0.0751 0.067 Uiso 1 1 calc R . . C23 C 0.5555(9) 0.3672(3) 0.0145(5) 0.074(3) Uani 1 1 d . . . H23A H 0.6342 0.3828 -0.0190 0.111 Uiso 1 1 calc R . . H23B H 0.4827 0.3920 0.0323 0.111 Uiso 1 1 calc R . . H23C H 0.5031 0.3424 -0.0213 0.111 Uiso 1 1 calc R . . C24 C 0.1866(6) 0.2777(2) 0.2180(4) 0.0327(14) Uani 1 1 d . . . H24A H 0.1163 0.2587 0.2534 0.039 Uiso 1 1 calc R . . H24B H 0.2442 0.3000 0.2574 0.039 Uiso 1 1 calc R . . C25 C 0.0942(7) 0.3083(2) 0.1522(4) 0.0423(16) Uani 1 1 d . . . H25A H 0.1611 0.3193 0.1060 0.051 Uiso 1 1 calc R . . H25B H 0.0141 0.2875 0.1250 0.051 Uiso 1 1 calc R . . C26 C 0.0221(8) 0.3525(3) 0.1926(5) 0.058(2) Uani 1 1 d . . . H26A H -0.0374 0.3705 0.1473 0.069 Uiso 1 1 calc R . . H26B H 0.1025 0.3747 0.2156 0.069 Uiso 1 1 calc R . . C27 C -0.0798(10) 0.3390(4) 0.2647(5) 0.088(3) Uani 1 1 d . . . H27A H -0.1218 0.3688 0.2896 0.132 Uiso 1 1 calc R . . H27B H -0.0216 0.3211 0.3097 0.132 Uiso 1 1 calc R . . H27C H -0.1623 0.3182 0.2417 0.132 Uiso 1 1 calc R . . C28 C 0.2821(6) 0.1703(2) 0.3025(3) 0.0260(13) Uani 1 1 d . . . C29 C 0.2246(6) 0.1966(2) 0.3725(4) 0.0259(13) Uani 1 1 d . . . C30 C 0.2325(6) 0.1227(2) 0.2794(3) 0.0276(13) Uani 1 1 d . . . C31 C 0.1146(6) 0.0973(2) 0.3295(4) 0.0300(13) Uani 1 1 d . . . C32 C -0.0011(7) 0.0733(2) 0.2842(4) 0.0437(17) Uani 1 1 d . . . H32 H -0.0037 0.0735 0.2226 0.052 Uiso 1 1 calc R . . C33 C -0.1127(7) 0.0493(3) 0.3276(5) 0.0538(19) Uani 1 1 d . . . H33 H -0.1931 0.0338 0.2956 0.065 Uiso 1 1 calc R . . C34 C -0.1085(8) 0.0474(3) 0.4171(5) 0.056(2) Uani 1 1 d . . . H34 H -0.1851 0.0306 0.4469 0.067 Uiso 1 1 calc R . . C35 C 0.0072(8) 0.0700(2) 0.4620(5) 0.0520(19) Uani 1 1 d . . . H35 H 0.0127 0.0682 0.5236 0.062 Uiso 1 1 calc R . . C36 C 0.1163(7) 0.0955(2) 0.4192(4) 0.0413(16) Uani 1 1 d . . . H36 H 0.1938 0.1122 0.4517 0.050 Uiso 1 1 calc R . . C37 C 0.3739(7) -0.0027(3) 0.3029(4) 0.0451(17) Uani 1 1 d . . . H37 H 0.3414 0.0243 0.2626 0.054 Uiso 1 1 calc R . . Br1 Br 0.77033(9) -0.02053(3) -0.08033(4) 0.0521(3) Uani 1 1 d . . . N1 N 0.1821(5) 0.2200(2) 0.4290(3) 0.0401(13) Uani 1 1 d . . . O1 O 0.6891(4) 0.15087(15) 0.2323(3) 0.0365(10) Uani 1 1 d . . . O2 O 0.8061(6) 0.19923(19) 0.1359(3) 0.0661(15) Uani 1 1 d . . . O3 O 0.2836(5) 0.09987(15) 0.2145(3) 0.0403(11) Uani 1 1 d . . . P1 P 0.31692(16) 0.23590(6) 0.16942(9) 0.0279(4) Uani 1 1 d . . . Cl1 Cl 0.4690(3) 0.02304(11) 0.3906(2) 0.1184(10) Uani 1 1 d . . . Cl2 Cl 0.2134(3) -0.03283(8) 0.33523(17) 0.0862(6) Uani 1 1 d . . . Cl3 Cl 0.4923(3) -0.04150(9) 0.24789(16) 0.0909(8) 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 0.035(3) 0.042(4) 0.039(4) -0.006(3) 0.005(3) 0.009(3) C2 0.029(3) 0.034(4) 0.031(3) -0.006(3) 0.002(3) 0.004(3) C3 0.047(4) 0.045(4) 0.043(4) 0.000(3) 0.012(3) -0.003(3) C4 0.055(4) 0.046(4) 0.038(4) -0.007(3) 0.019(3) 0.000(3) C5 0.048(4) 0.038(4) 0.028(3) -0.006(3) -0.002(3) 0.004(3) C6 0.059(4) 0.036(4) 0.040(4) -0.005(3) 0.008(3) -0.005(3) C7 0.051(4) 0.047(4) 0.030(4) -0.002(3) 0.011(3) 0.000(3) C8 0.032(3) 0.034(4) 0.032(3) -0.006(3) 0.001(3) 0.004(3) C9 0.024(3) 0.061(5) 0.056(5) -0.008(4) -0.007(3) 0.006(3) C10 0.033(4) 0.058(5) 0.047(4) -0.020(4) -0.006(3) 0.000(3) C11 0.041(4) 0.046(4) 0.039(4) -0.012(3) 0.003(3) -0.008(3) C12 0.033(3) 0.038(4) 0.034(4) -0.005(3) 0.004(3) -0.004(3) C13 0.025(3) 0.033(3) 0.022(3) 0.000(3) 0.002(2) 0.001(2) C14 0.027(3) 0.026(3) 0.024(3) -0.002(2) 0.006(2) 0.005(2) C15 0.037(3) 0.032(3) 0.025(3) 0.007(3) -0.003(3) -0.004(3) C16 0.048(4) 0.040(4) 0.026(3) -0.002(3) 0.003(3) 0.002(3) C17 0.061(4) 0.041(4) 0.041(4) -0.006(3) -0.006(3) 0.003(3) C18 0.086(6) 0.058(5) 0.045(5) -0.015(4) 0.014(4) 0.002(4) C20 0.043(4) 0.036(4) 0.035(4) 0.001(3) 0.005(3) 0.001(3) C21 0.058(4) 0.044(4) 0.040(4) -0.004(3) 0.003(3) -0.014(3) C22 0.065(5) 0.044(4) 0.058(5) 0.010(4) 0.000(4) -0.018(4) C23 0.079(6) 0.082(6) 0.060(5) 0.007(5) -0.008(4) -0.028(5) C24 0.037(3) 0.036(4) 0.026(3) 0.001(3) 0.006(3) 0.009(3) C25 0.048(4) 0.040(4) 0.038(4) 0.002(3) -0.003(3) 0.014(3) C26 0.059(5) 0.054(5) 0.060(5) 0.000(4) 0.002(4) 0.029(4) C27 0.084(6) 0.126(9) 0.056(5) -0.004(5) 0.015(5) 0.054(6) C28 0.028(3) 0.033(3) 0.017(3) -0.003(2) 0.003(2) -0.001(2) C29 0.021(3) 0.029(3) 0.027(3) 0.003(3) -0.002(2) -0.003(2) C30 0.034(3) 0.032(3) 0.016(3) 0.002(3) -0.003(2) 0.005(3) C31 0.034(3) 0.021(3) 0.035(3) 0.003(3) 0.007(3) 0.005(2) C32 0.044(4) 0.041(4) 0.046(4) 0.007(3) -0.004(3) -0.002(3) C33 0.033(4) 0.057(5) 0.071(6) 0.005(4) -0.001(4) -0.008(3) C34 0.046(4) 0.042(4) 0.081(6) 0.012(4) 0.021(4) -0.007(3) C35 0.065(5) 0.049(5) 0.042(4) 0.008(3) 0.021(4) -0.002(4) C36 0.047(4) 0.044(4) 0.033(4) 0.001(3) 0.008(3) -0.006(3) C37 0.052(4) 0.042(4) 0.042(4) 0.006(3) 0.008(3) 0.005(3) Br1 0.0736(5) 0.0440(5) 0.0391(4) -0.0108(3) 0.0078(3) 0.0045(4) N1 0.037(3) 0.052(4) 0.031(3) -0.012(3) 0.005(2) -0.002(3) O1 0.031(2) 0.038(3) 0.041(3) -0.009(2) 0.0069(19) 0.0041(18) O2 0.098(4) 0.040(3) 0.062(3) -0.009(3) 0.029(3) -0.017(3) O3 0.061(3) 0.031(2) 0.030(2) -0.007(2) 0.014(2) -0.008(2) P1 0.0297(8) 0.0294(9) 0.0247(8) 0.0008(7) 0.0030(6) 0.0016(6) Cl1 0.109(2) 0.111 0.131(2) -0.0542(17) -0.0497(19) 0.0284(17) Cl2 0.0864(16) 0.0614(14) 0.113 0.0257(13) 0.0419(13) 0.0054(11) Cl3 0.1120(19) 0.0822(17) 0.0819(16) 0.0082(13) 0.0477(14) 0.0418(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.186(7) . ? C1 O1 1.369(7) . ? C1 C2 1.489(8) . ? C2 C7 1.386(8) . ? C2 C3 1.393(8) . ? C3 C4 1.374(9) . ? C3 H3 0.9500 . ? C4 C5 1.377(9) . ? C4 H4 0.9500 . ? C5 C6 1.394(9) . ? C5 Br1 1.897(6) . ? C6 C7 1.369(8) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.369(8) . ? C8 C9 1.378(8) . ? C8 O1 1.419(7) . ? C9 C10 1.372(9) . ? C9 H9 0.9500 . ? C10 C11 1.374(8) . ? C10 H10 0.9500 . ? C11 C12 1.393(8) . ? C11 H11 0.9500 . ? C12 C13 1.391(8) . ? C12 H12 0.9500 . ? C13 C14 1.528(7) . ? C14 C28 1.521(7) . ? C14 P1 1.829(5) . ? C14 H14 1.0000 . ? C15 C16 1.534(8) . ? C15 P1 1.797(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.499(8) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.521(9) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C20 C21 1.521(8) . ? C20 P1 1.808(6) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.540(9) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.512(9) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.527(8) . ? C24 P1 1.804(6) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.511(9) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.502(11) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C29 1.408(8) . ? C28 C30 1.412(7) . ? C29 N1 1.154(7) . ? C30 O3 1.276(6) . ? C30 C31 1.492(8) . ? C31 C32 1.382(8) . ? C31 C36 1.384(8) . ? C32 C33 1.380(9) . ? C32 H32 0.9500 . ? C33 C34 1.381(10) . ? C33 H33 0.9500 . ? C34 C35 1.363(9) . ? C34 H34 0.9500 . ? C35 C36 1.378(9) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 Cl1 1.717(7) . ? C37 Cl2 1.729(7) . ? C37 Cl3 1.734(7) . ? C37 H37 1.0000 . ? 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 O2 C1 O1 125.0(6) . . ? O2 C1 C2 125.2(6) . . ? O1 C1 C2 109.8(6) . . ? C7 C2 C3 118.7(6) . . ? C7 C2 C1 123.9(6) . . ? C3 C2 C1 117.4(6) . . ? C4 C3 C2 120.6(6) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 119.5(6) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C4 C5 C6 120.9(6) . . ? C4 C5 Br1 119.8(5) . . ? C6 C5 Br1 119.2(5) . . ? C7 C6 C5 118.7(6) . . ? C7 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C6 C7 C2 121.5(6) . . ? C6 C7 H7 119.3 . . ? C2 C7 H7 119.3 . . ? C13 C8 C9 122.6(6) . . ? C13 C8 O1 118.1(5) . . ? C9 C8 O1 119.2(5) . . ? C10 C9 C8 119.6(6) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C11 C10 C9 119.9(6) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 119.5(6) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C13 C12 C11 121.4(6) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C8 C13 C12 116.9(5) . . ? C8 C13 C14 120.0(5) . . ? C12 C13 C14 123.0(5) . . ? C28 C14 C13 115.7(4) . . ? C28 C14 P1 110.1(4) . . ? C13 C14 P1 116.2(4) . . ? C28 C14 H14 104.4 . . ? C13 C14 H14 104.4 . . ? P1 C14 H14 104.4 . . ? C16 C15 P1 114.0(4) . . ? C16 C15 H15A 108.8 . . ? P1 C15 H15A 108.8 . . ? C16 C15 H15B 108.8 . . ? P1 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C15 113.5(5) . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16B 108.9 . . ? C15 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C16 C17 C18 112.0(6) . . ? C16 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? C16 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C21 C20 P1 117.0(4) . . ? C21 C20 H20A 108.0 . . ? P1 C20 H20A 108.0 . . ? C21 C20 H20B 108.0 . . ? P1 C20 H20B 108.0 . . ? H20A C20 H20B 107.3 . . ? C20 C21 C22 111.0(5) . . ? C20 C21 H21A 109.4 . . ? C22 C21 H21A 109.4 . . ? C20 C21 H21B 109.4 . . ? C22 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? C23 C22 C21 115.3(6) . . ? C23 C22 H22A 108.5 . . ? C21 C22 H22A 108.5 . . ? C23 C22 H22B 108.5 . . ? C21 C22 H22B 108.5 . . ? H22A C22 H22B 107.5 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 P1 113.9(4) . . ? C25 C24 H24A 108.8 . . ? P1 C24 H24A 108.8 . . ? C25 C24 H24B 108.8 . . ? P1 C24 H24B 108.8 . . ? H24A C24 H24B 107.7 . . ? C26 C25 C24 112.8(5) . . ? C26 C25 H25A 109.0 . . ? C24 C25 H25A 109.0 . . ? C26 C25 H25B 109.0 . . ? C24 C25 H25B 109.0 . . ? H25A C25 H25B 107.8 . . ? C25 C26 C27 112.5(7) . . ? C25 C26 H26A 109.1 . . ? C27 C26 H26A 109.1 . . ? C25 C26 H26B 109.1 . . ? C27 C26 H26B 109.1 . . ? H26A C26 H26B 107.8 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 C30 123.1(5) . . ? C29 C28 C14 118.9(5) . . ? C30 C28 C14 117.9(5) . . ? N1 C29 C28 176.8(6) . . ? O3 C30 C28 122.1(5) . . ? O3 C30 C31 116.9(5) . . ? C28 C30 C31 120.9(5) . . ? C32 C31 C36 118.1(6) . . ? C32 C31 C30 118.5(5) . . ? C36 C31 C30 123.4(5) . . ? C31 C32 C33 120.6(6) . . ? C31 C32 H32 119.7 . . ? C33 C32 H32 119.7 . . ? C34 C33 C32 120.6(6) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C33 C34 C35 119.0(7) . . ? C33 C34 H34 120.5 . . ? C35 C34 H34 120.5 . . ? C36 C35 C34 120.7(7) . . ? C36 C35 H35 119.6 . . ? C34 C35 H35 119.6 . . ? C35 C36 C31 120.9(6) . . ? C35 C36 H36 119.5 . . ? C31 C36 H36 119.5 . . ? Cl1 C37 Cl2 110.6(4) . . ? Cl1 C37 Cl3 110.4(4) . . ? Cl2 C37 Cl3 111.5(4) . . ? Cl1 C37 H37 108.1 . . ? Cl2 C37 H37 108.1 . . ? Cl3 C37 H37 108.1 . . ? C1 O1 C8 116.1(5) . . ? C24 P1 C15 109.8(3) . . ? C24 P1 C20 109.7(3) . . ? C15 P1 C20 106.7(3) . . ? C24 P1 C14 112.2(3) . . ? C15 P1 C14 105.6(3) . . ? C20 P1 C14 112.6(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.159 _refine_diff_density_min -1.430 _refine_diff_density_rms 0.171 _database_code_depnum_ccdc_archive 'CCDC 881549' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a12767 #TrackingRef 'a12767.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H22 Br N O3' _chemical_formula_sum 'C28 H22 Br N O3' _chemical_formula_weight 500.38 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.4196(15) _cell_length_b 13.915(2) _cell_length_c 17.027(2) _cell_angle_alpha 67.414(12) _cell_angle_beta 89.449(9) _cell_angle_gamma 67.009(8) _cell_volume 2466.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 1.695 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4613 _exptl_absorpt_correction_T_max 0.8763 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18122 _diffrn_reflns_av_R_equivalents 0.0757 _diffrn_reflns_av_sigmaI/netI 0.1658 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.03 _reflns_number_total 8323 _reflns_number_gt 3485 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1355P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8323 _refine_ls_number_parameters 599 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2041 _refine_ls_R_factor_gt 0.0821 _refine_ls_wR_factor_ref 0.2642 _refine_ls_wR_factor_gt 0.2058 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 C1 C 1.1926(6) 0.6421(7) 0.4905(5) 0.046(2) Uani 1 1 d . . . C2 C 1.1600(7) 0.6985(7) 0.5443(5) 0.050(2) Uani 1 1 d . . . H2 H 1.2150 0.7171 0.5669 0.060 Uiso 1 1 calc R . . C3 C 1.0473(7) 0.7276(7) 0.5649(5) 0.047(2) Uani 1 1 d . . . H3 H 1.0249 0.7669 0.6015 0.056 Uiso 1 1 calc R . . C4 C 0.9673(7) 0.7004(6) 0.5333(5) 0.0407(19) Uani 1 1 d . C . C5 C 0.9992(7) 0.6444(7) 0.4784(5) 0.051(2) Uani 1 1 d . . . H5 H 0.9444 0.6261 0.4553 0.061 Uiso 1 1 calc R . . C6 C 1.1133(7) 0.6161(7) 0.4582(5) 0.054(2) Uani 1 1 d . . . H6 H 1.1361 0.5777 0.4211 0.065 Uiso 1 1 calc R . . C7 C 0.8445(7) 0.7368(7) 0.5513(5) 0.043(2) Uani 1 1 d . . . C8 C 0.7741(6) 0.8212(7) 0.5754(4) 0.0370(19) Uani 1 1 d . C . C9 C 0.6614(6) 0.8129(7) 0.5819(5) 0.044(2) Uani 1 1 d . . . C10 C 0.5561(7) 0.8734(8) 0.6032(5) 0.055(2) Uani 1 1 d . C . H10 H 0.5475 0.9350 0.6179 0.066 Uiso 1 1 calc R . . C11 C 0.4641(8) 0.8417(9) 0.6025(6) 0.064(3) Uani 1 1 d . . . H11 H 0.3902 0.8831 0.6154 0.077 Uiso 1 1 calc R C . C12 C 0.4795(8) 0.7486(11) 0.5828(6) 0.086(4) Uani 1 1 d . C . H12 H 0.4151 0.7277 0.5836 0.103 Uiso 1 1 calc R . . C13 C 0.5839(9) 0.6858(9) 0.5624(6) 0.076(3) Uani 1 1 d . . . H13 H 0.5936 0.6226 0.5494 0.091 Uiso 1 1 calc R C . C14 C 0.6739(7) 0.7218(8) 0.5621(5) 0.054(2) Uani 1 1 d . C . C15 C 0.8042(6) 0.9059(7) 0.5877(5) 0.0363(19) Uani 1 1 d . . . C16 C 0.8266(6) 0.9850(8) 0.5131(5) 0.043(2) Uani 1 1 d . C . C17 C 0.8074(6) 0.9127(7) 0.6653(5) 0.043(2) Uani 1 1 d . A . C18 C 0.8452(6) 0.9862(7) 0.6899(5) 0.044(2) Uani 1 1 d . . . C19 C 0.9271(7) 1.0241(7) 0.6531(5) 0.049(2) Uani 1 1 d . C . H19 H 0.9608 1.0033 0.6086 0.059 Uiso 1 1 calc R . . C20 C 0.9627(7) 1.0913(7) 0.6783(5) 0.056(2) Uani 1 1 d . . . H20 H 1.0184 1.1182 0.6507 0.067 Uiso 1 1 calc R C . C21 C 0.9166(8) 1.1186(8) 0.7435(6) 0.069(3) Uani 1 1 d . C . H21 H 0.9413 1.1640 0.7622 0.083 Uiso 1 1 calc R . . C22 C 0.8334(9) 1.0806(8) 0.7833(6) 0.075(3) Uani 1 1 d . . . H22 H 0.8013 1.1008 0.8284 0.090 Uiso 1 1 calc R C . C23 C 0.7979(7) 1.0143(8) 0.7575(5) 0.060(2) Uani 1 1 d . C . H23 H 0.7419 0.9876 0.7849 0.073 Uiso 1 1 calc R . . C24 C 0.8580(10) 0.7337(9) 0.7801(5) 0.056(2) Uani 1 1 d . A . C25 C 0.8125(9) 0.6615(9) 0.8504(6) 0.069(3) Uani 1 1 d . . . C26 C 0.7256(10) 0.6369(10) 0.8090(7) 0.112(4) Uani 1 1 d . A . H26A H 0.6554 0.7085 0.7772 0.168 Uiso 1 1 calc R . . H26B H 0.7019 0.5829 0.8537 0.168 Uiso 1 1 calc R . . H26C H 0.7628 0.6035 0.7691 0.168 Uiso 1 1 calc R . . C27 C 0.9158(12) 0.5463(12) 0.9015(8) 0.153(6) Uani 1 1 d . A . H27A H 0.9502 0.5098 0.8626 0.229 Uiso 1 1 calc R . . H27B H 0.8875 0.4969 0.9463 0.229 Uiso 1 1 calc R . . H27C H 0.9763 0.5580 0.9284 0.229 Uiso 1 1 calc R . . C28 C 0.788(3) 0.702(2) 0.9154(15) 0.083(9) Uiso 0.56(4) 1 d P A 1 H28A H 0.7586 0.6532 0.9605 0.124 Uiso 0.56(4) 1 calc PR A 1 H28B H 0.7269 0.7808 0.8908 0.124 Uiso 0.56(4) 1 calc PR A 1 H28C H 0.8600 0.6990 0.9405 0.124 Uiso 0.56(4) 1 calc PR A 1 C28' C 0.711(4) 0.745(3) 0.887(2) 0.096(12) Uiso 0.44(4) 1 d P A 2 H28D H 0.6813 0.6989 0.9334 0.145 Uiso 0.44(4) 1 calc PR A 2 H28E H 0.6456 0.8036 0.8405 0.145 Uiso 0.44(4) 1 calc PR A 2 H28F H 0.7469 0.7827 0.9104 0.145 Uiso 0.44(4) 1 calc PR A 2 C29 C 0.6958(7) 0.6374(7) 1.2353(6) 0.056(2) Uani 1 1 d . . . C30 C 0.6651(7) 0.6927(7) 1.1480(5) 0.056(2) Uani 1 1 d . . . H30 H 0.7220 0.7088 1.1139 0.068 Uiso 1 1 calc R . . C31 C 0.5540(7) 0.7251(7) 1.1088(5) 0.052(2) Uani 1 1 d . . . H31 H 0.5342 0.7633 1.0477 0.062 Uiso 1 1 calc R . . C32 C 0.4686(7) 0.7024(6) 1.1581(5) 0.043(2) Uani 1 1 d . . . C33 C 0.5022(8) 0.6429(7) 1.2477(5) 0.054(2) Uani 1 1 d . . . H33 H 0.4468 0.6235 1.2820 0.065 Uiso 1 1 calc R . . C34 C 0.6123(9) 0.6125(8) 1.2864(5) 0.062(2) Uani 1 1 d . . . H34 H 0.6331 0.5746 1.3474 0.074 Uiso 1 1 calc R . . C35 C 0.3490(7) 0.7365(7) 1.1177(5) 0.050(2) Uani 1 1 d . . . C36 C 0.2838(7) 0.8160(7) 1.0413(5) 0.047(2) Uani 1 1 d . . . C37 C 0.1686(7) 0.8113(8) 1.0399(6) 0.054(2) Uani 1 1 d . . . C38 C 0.0621(8) 0.8730(8) 0.9790(6) 0.066(3) Uani 1 1 d . . . H38 H 0.0553 0.9314 0.9242 0.079 Uiso 1 1 calc R . . C39 C -0.0312(8) 0.8437(10) 1.0034(8) 0.079(3) Uani 1 1 d . . . H39 H -0.1045 0.8824 0.9652 0.095 Uiso 1 1 calc R . . C40 C -0.0180(10) 0.7586(11) 1.0830(10) 0.092(4) Uani 1 1 d . . . H40 H -0.0833 0.7392 1.0964 0.111 Uiso 1 1 calc R . . C41 C 0.0842(10) 0.6977(9) 1.1463(8) 0.080(3) Uani 1 1 d . . . H41 H 0.0896 0.6423 1.2022 0.096 Uiso 1 1 calc R . . C42 C 0.1761(8) 0.7276(8) 1.1178(6) 0.057(2) Uani 1 1 d . . . C43 C 0.3151(6) 0.9011(7) 0.9713(5) 0.046(2) Uani 1 1 d . . . C44 C 0.3336(7) 0.9844(7) 0.9944(5) 0.046(2) Uani 1 1 d . . . C45 C 0.3163(6) 0.9092(7) 0.8898(5) 0.047(2) Uani 1 1 d . B . C46 C 0.3502(7) 0.9840(7) 0.8177(5) 0.047(2) Uani 1 1 d . . . C47 C 0.4326(7) 1.0224(7) 0.8286(5) 0.047(2) Uani 1 1 d . . . H47 H 0.4704 0.9992 0.8851 0.056 Uiso 1 1 calc R . . C48 C 0.4615(7) 1.0946(8) 0.7585(6) 0.062(2) Uani 1 1 d . . . H48 H 0.5197 1.1195 0.7674 0.074 Uiso 1 1 calc R . . C49 C 0.4072(9) 1.1306(8) 0.6766(6) 0.069(3) Uani 1 1 d . . . H49 H 0.4259 1.1816 0.6287 0.082 Uiso 1 1 calc R . . C50 C 0.3236(9) 1.0910(9) 0.6642(6) 0.078(3) Uani 1 1 d . . . H50 H 0.2863 1.1139 0.6076 0.093 Uiso 1 1 calc R . . C51 C 0.2958(7) 1.0195(7) 0.7337(5) 0.058(2) Uani 1 1 d . . . H51 H 0.2386 0.9934 0.7249 0.069 Uiso 1 1 calc R . . C52 C 0.3648(8) 0.7301(8) 0.8839(5) 0.051(2) Uani 1 1 d . B . C53 C 0.3172(8) 0.6616(8) 0.8559(5) 0.057(2) Uani 1 1 d . . . C54 C 0.273(3) 0.599(3) 0.9310(13) 0.083(7) Uiso 0.71(6) 1 d P B 3 H54A H 0.2097 0.6542 0.9468 0.124 Uiso 0.71(6) 1 calc PR B 3 H54B H 0.3379 0.5488 0.9799 0.124 Uiso 0.71(6) 1 calc PR B 3 H54C H 0.2413 0.5528 0.9158 0.124 Uiso 0.71(6) 1 calc PR B 3 C54' C 0.215(6) 0.650(6) 0.908(3) 0.072(16) Uiso 0.29(6) 1 d P B 4 H54D H 0.1635 0.7250 0.9071 0.109 Uiso 0.29(6) 1 calc PR B 4 H54E H 0.2489 0.5945 0.9675 0.109 Uiso 0.29(6) 1 calc PR B 4 H54F H 0.1684 0.6244 0.8813 0.109 Uiso 0.29(6) 1 calc PR B 4 C55 C 0.4043(12) 0.5766(10) 0.8402(8) 0.129(5) Uani 1 1 d . B . H55A H 0.3690 0.5350 0.8221 0.193 Uiso 1 1 calc R . . H55B H 0.4625 0.5234 0.8929 0.193 Uiso 1 1 calc R . . H55C H 0.4437 0.6106 0.7945 0.193 Uiso 1 1 calc R . . C56 C 0.2273(11) 0.7385(10) 0.7731(7) 0.114(4) Uani 1 1 d . B . H56A H 0.1621 0.7993 0.7822 0.171 Uiso 1 1 calc R . . H56B H 0.1960 0.6928 0.7568 0.171 Uiso 1 1 calc R . . H56C H 0.2659 0.7728 0.7268 0.171 Uiso 1 1 calc R . . O1 O 0.7847(5) 0.6745(5) 0.5428(3) 0.0505(14) Uani 1 1 d . C . O2 O 0.7709(4) 0.8409(5) 0.7296(3) 0.0457(14) Uani 1 1 d . . . O3 O 0.9576(6) 0.7084(6) 0.7666(4) 0.083(2) Uani 1 1 d . . . O4 O 0.2875(5) 0.6784(5) 1.1677(4) 0.0590(15) Uani 1 1 d . . . O5 O 0.2790(5) 0.8352(5) 0.8723(3) 0.0472(14) Uani 1 1 d . . . O6 O 0.4626(6) 0.7010(6) 0.9143(5) 0.095(2) Uani 1 1 d . . . Br1 Br 1.34551(8) 0.60824(9) 0.46037(6) 0.0748(4) Uani 1 1 d . . . Br2 Br 0.85041(9) 0.59436(11) 1.28975(7) 0.0919(5) Uani 1 1 d . . . N1 N 0.8405(5) 1.0480(6) 0.4501(5) 0.0533(19) Uani 1 1 d . . . N2 N 0.3450(6) 1.0485(7) 1.0168(4) 0.062(2) 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 0.044(5) 0.049(6) 0.051(5) -0.027(5) 0.013(4) -0.019(4) C2 0.040(5) 0.046(6) 0.065(6) -0.021(5) -0.002(4) -0.020(4) C3 0.042(5) 0.058(6) 0.050(5) -0.032(5) 0.011(4) -0.022(5) C4 0.050(5) 0.039(5) 0.045(5) -0.022(4) 0.011(4) -0.026(4) C5 0.056(6) 0.050(6) 0.059(6) -0.032(5) 0.006(4) -0.026(5) C6 0.064(6) 0.060(6) 0.053(5) -0.039(5) 0.018(4) -0.025(5) C7 0.050(5) 0.043(6) 0.040(5) -0.010(4) -0.001(4) -0.031(5) C8 0.029(4) 0.044(5) 0.044(5) -0.022(4) 0.006(3) -0.017(4) C9 0.038(5) 0.063(6) 0.038(5) -0.020(5) 0.006(4) -0.028(5) C10 0.044(5) 0.084(7) 0.046(5) -0.027(5) 0.008(4) -0.036(5) C11 0.052(6) 0.082(8) 0.067(6) -0.039(6) 0.007(4) -0.029(6) C12 0.041(6) 0.146(11) 0.088(8) -0.049(8) 0.029(5) -0.055(7) C13 0.087(8) 0.090(8) 0.087(7) -0.048(7) 0.010(6) -0.063(7) C14 0.041(5) 0.082(7) 0.057(5) -0.036(5) 0.013(4) -0.038(5) C15 0.025(4) 0.050(5) 0.035(4) -0.013(4) 0.006(3) -0.021(4) C16 0.036(5) 0.062(6) 0.039(5) -0.026(5) 0.004(4) -0.025(5) C17 0.040(5) 0.055(6) 0.035(5) -0.015(4) 0.009(3) -0.025(4) C18 0.042(5) 0.054(6) 0.047(5) -0.030(5) 0.016(4) -0.022(4) C19 0.053(5) 0.066(6) 0.039(5) -0.023(5) 0.010(4) -0.035(5) C20 0.060(6) 0.059(6) 0.058(6) -0.023(5) 0.006(4) -0.035(5) C21 0.082(7) 0.083(8) 0.071(7) -0.042(6) 0.008(5) -0.052(6) C22 0.107(8) 0.086(8) 0.076(7) -0.058(7) 0.040(6) -0.061(7) C23 0.059(6) 0.081(7) 0.058(6) -0.037(6) 0.029(4) -0.037(5) C24 0.075(7) 0.073(8) 0.044(5) -0.024(6) 0.016(5) -0.054(7) C25 0.100(8) 0.072(8) 0.057(6) -0.016(6) 0.017(6) -0.068(7) C26 0.124(10) 0.132(11) 0.091(8) -0.012(8) -0.005(7) -0.097(9) C27 0.172(14) 0.144(14) 0.091(9) 0.051(9) -0.021(9) -0.114(12) C29 0.056(6) 0.056(6) 0.057(6) -0.021(5) 0.003(4) -0.026(5) C30 0.060(6) 0.068(7) 0.038(5) -0.010(5) 0.011(4) -0.035(5) C31 0.056(6) 0.056(6) 0.045(5) -0.014(5) 0.010(4) -0.032(5) C32 0.049(5) 0.037(5) 0.045(5) -0.019(4) 0.013(4) -0.016(4) C33 0.064(6) 0.053(6) 0.041(5) -0.015(5) 0.007(4) -0.025(5) C34 0.087(7) 0.069(7) 0.031(5) -0.010(5) 0.007(5) -0.044(6) C35 0.059(6) 0.053(6) 0.042(5) -0.018(5) 0.016(5) -0.028(5) C36 0.050(5) 0.053(6) 0.057(6) -0.030(5) 0.015(4) -0.032(5) C37 0.060(6) 0.067(7) 0.061(6) -0.040(6) 0.025(5) -0.040(5) C38 0.062(6) 0.078(7) 0.075(7) -0.040(6) 0.014(5) -0.040(6) C39 0.056(7) 0.100(9) 0.102(9) -0.047(8) 0.018(6) -0.049(7) C40 0.079(9) 0.101(10) 0.140(12) -0.071(10) 0.042(8) -0.059(8) C41 0.086(8) 0.089(9) 0.103(9) -0.049(7) 0.048(7) -0.064(7) C42 0.070(7) 0.056(7) 0.067(7) -0.035(6) 0.023(5) -0.037(6) C43 0.046(5) 0.052(6) 0.048(5) -0.023(5) 0.009(4) -0.028(4) C44 0.050(5) 0.054(6) 0.041(5) -0.019(5) 0.009(4) -0.027(5) C45 0.038(5) 0.057(6) 0.050(5) -0.025(5) 0.005(4) -0.020(4) C46 0.047(5) 0.055(6) 0.046(5) -0.027(5) 0.011(4) -0.020(5) C47 0.050(5) 0.054(6) 0.049(5) -0.027(5) 0.014(4) -0.029(5) C48 0.066(6) 0.069(7) 0.072(7) -0.034(6) 0.021(5) -0.044(5) C49 0.094(7) 0.074(7) 0.040(6) -0.017(5) 0.020(5) -0.043(6) C50 0.109(8) 0.081(8) 0.029(5) 0.003(5) -0.008(5) -0.052(7) C51 0.066(6) 0.064(7) 0.048(6) -0.027(5) -0.002(4) -0.028(5) C52 0.047(6) 0.057(7) 0.055(5) -0.027(5) 0.003(4) -0.026(5) C53 0.074(6) 0.052(6) 0.057(6) -0.015(5) 0.006(5) -0.045(5) C55 0.210(15) 0.082(9) 0.161(13) -0.096(10) 0.033(10) -0.080(10) C56 0.168(11) 0.116(10) 0.085(8) -0.028(8) -0.027(8) -0.097(9) O1 0.053(4) 0.061(4) 0.055(3) -0.032(3) 0.009(3) -0.033(3) O2 0.046(3) 0.058(4) 0.038(3) -0.013(3) 0.010(3) -0.034(3) O3 0.066(5) 0.081(5) 0.075(5) -0.004(4) 0.013(4) -0.033(4) O4 0.069(4) 0.078(5) 0.055(4) -0.034(3) 0.027(3) -0.049(4) O5 0.049(3) 0.052(4) 0.055(3) -0.028(3) 0.004(3) -0.029(3) O6 0.056(4) 0.087(6) 0.152(7) -0.072(5) -0.012(4) -0.018(4) Br1 0.0563(6) 0.0949(9) 0.0856(8) -0.0483(7) 0.0303(5) -0.0334(6) Br2 0.0780(8) 0.1127(10) 0.0675(7) -0.0173(7) -0.0129(5) -0.0417(7) N1 0.051(4) 0.062(5) 0.046(4) -0.018(4) 0.015(3) -0.027(4) N2 0.068(5) 0.074(6) 0.066(5) -0.038(5) 0.014(4) -0.043(5) _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 C1 C6 1.358(10) . ? C1 C2 1.385(10) . ? C1 Br1 1.886(7) . ? C2 C3 1.379(10) . ? C2 H2 0.9500 . ? C3 C4 1.371(10) . ? C3 H3 0.9500 . ? C4 C5 1.397(10) . ? C4 C7 1.477(10) . ? C5 C6 1.392(10) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.370(10) . ? C7 O1 1.388(8) . ? C8 C9 1.448(9) . ? C8 C15 1.451(10) . ? C9 C10 1.384(10) . ? C9 C14 1.386(11) . ? C10 C11 1.377(11) . ? C10 H10 0.9500 . ? C11 C12 1.403(13) . ? C11 H11 0.9500 . ? C12 C13 1.381(12) . ? C12 H12 0.9500 . ? C13 C14 1.391(11) . ? C13 H13 0.9500 . ? C14 O1 1.373(9) . ? C15 C17 1.363(9) . ? C15 C16 1.435(11) . ? C16 N1 1.158(9) . ? C17 O2 1.381(9) . ? C17 C18 1.466(10) . ? C18 C19 1.363(10) . ? C18 C23 1.405(10) . ? C19 C20 1.374(11) . ? C19 H19 0.9500 . ? C20 C21 1.358(11) . ? C20 H20 0.9500 . ? C21 C22 1.393(12) . ? C21 H21 0.9500 . ? C22 C23 1.368(11) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 O3 1.192(9) . ? C24 O2 1.380(10) . ? C24 C25 1.507(11) . ? C25 C28 1.404(18) . ? C25 C26 1.505(12) . ? C25 C27 1.522(15) . ? C25 C28' 1.66(3) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C28' H28D 0.9800 . ? C28' H28E 0.9800 . ? C28' H28F 0.9800 . ? C29 C30 1.361(11) . ? C29 C34 1.408(11) . ? C29 Br2 1.901(8) . ? C30 C31 1.361(10) . ? C30 H30 0.9500 . ? C31 C32 1.404(10) . ? C31 H31 0.9500 . ? C32 C33 1.400(10) . ? C32 C35 1.457(11) . ? C33 C34 1.355(11) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? C35 C36 1.337(11) . ? C35 O4 1.379(9) . ? C36 C37 1.458(11) . ? C36 C43 1.497(11) . ? C37 C42 1.361(11) . ? C37 C38 1.421(11) . ? C38 C39 1.382(12) . ? C38 H38 0.9500 . ? C39 C40 1.373(14) . ? C39 H39 0.9500 . ? C40 C41 1.405(14) . ? C40 H40 0.9500 . ? C41 C42 1.385(12) . ? C41 H41 0.9500 . ? C42 O4 1.394(10) . ? C43 C45 1.350(10) . ? C43 C44 1.453(11) . ? C44 N2 1.150(9) . ? C45 O5 1.404(9) . ? C45 C46 1.457(11) . ? C46 C47 1.369(10) . ? C46 C51 1.400(10) . ? C47 C48 1.384(11) . ? C47 H47 0.9500 . ? C48 C49 1.367(11) . ? C48 H48 0.9500 . ? C49 C50 1.402(12) . ? C49 H49 0.9500 . ? C50 C51 1.366(12) . ? C50 H50 0.9500 . ? C51 H51 0.9500 . ? C52 O6 1.173(9) . ? C52 O5 1.370(9) . ? C52 C53 1.509(11) . ? C53 C55 1.370(13) . ? C53 C54 1.485(16) . ? C53 C56 1.523(13) . ? C53 C54' 1.56(4) . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? C54' H54D 0.9800 . ? C54' H54E 0.9800 . ? C54' H54F 0.9800 . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C55 H55C 0.9800 . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? 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 119.7(7) . . ? C6 C1 Br1 121.6(6) . . ? C2 C1 Br1 118.7(6) . . ? C3 C2 C1 119.8(7) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C4 C3 C2 120.8(7) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.8(7) . . ? C3 C4 C7 121.1(7) . . ? C5 C4 C7 119.0(7) . . ? C6 C5 C4 118.6(7) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C1 C6 C5 121.4(7) . . ? C1 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C8 C7 O1 110.9(6) . . ? C8 C7 C4 133.4(7) . . ? O1 C7 C4 115.7(7) . . ? C7 C8 C9 106.3(7) . . ? C7 C8 C15 126.8(6) . . ? C9 C8 C15 126.8(7) . . ? C10 C9 C14 120.6(7) . . ? C10 C9 C8 133.7(8) . . ? C14 C9 C8 105.7(7) . . ? C11 C10 C9 118.1(8) . . ? C11 C10 H10 120.9 . . ? C9 C10 H10 120.9 . . ? C10 C11 C12 120.1(8) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 123.0(9) . . ? C13 C12 H12 118.5 . . ? C11 C12 H12 118.5 . . ? C12 C13 C14 115.2(9) . . ? C12 C13 H13 122.4 . . ? C14 C13 H13 122.4 . . ? O1 C14 C9 110.9(7) . . ? O1 C14 C13 126.1(8) . . ? C9 C14 C13 123.0(8) . . ? C17 C15 C16 121.4(7) . . ? C17 C15 C8 121.9(7) . . ? C16 C15 C8 116.7(6) . . ? N1 C16 C15 176.1(8) . . ? C15 C17 O2 116.1(7) . . ? C15 C17 C18 128.5(7) . . ? O2 C17 C18 115.4(6) . . ? C19 C18 C23 118.8(7) . . ? C19 C18 C17 123.3(6) . . ? C23 C18 C17 117.8(7) . . ? C18 C19 C20 122.2(7) . . ? C18 C19 H19 118.9 . . ? C20 C19 H19 118.9 . . ? C21 C20 C19 118.8(8) . . ? C21 C20 H20 120.6 . . ? C19 C20 H20 120.6 . . ? C20 C21 C22 120.7(8) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C23 C22 C21 120.2(8) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C18 119.2(8) . . ? C22 C23 H23 120.4 . . ? C18 C23 H23 120.4 . . ? O3 C24 O2 119.9(8) . . ? O3 C24 C25 127.1(10) . . ? O2 C24 C25 113.0(9) . . ? C28 C25 C26 122.6(15) . . ? C28 C25 C24 111.0(10) . . ? C26 C25 C24 108.4(8) . . ? C28 C25 C27 99.1(15) . . ? C26 C25 C27 106.3(9) . . ? C24 C25 C27 108.2(9) . . ? C28 C25 C28' 33.4(10) . . ? C26 C25 C28' 94.7(16) . . ? C24 C25 C28' 108.8(12) . . ? C27 C25 C28' 128.3(15) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C25 C28' H28D 109.5 . . ? C25 C28' H28E 109.5 . . ? H28D C28' H28E 109.5 . . ? C25 C28' H28F 109.5 . . ? H28D C28' H28F 109.5 . . ? H28E C28' H28F 109.5 . . ? C30 C29 C34 120.0(8) . . ? C30 C29 Br2 120.7(7) . . ? C34 C29 Br2 119.4(7) . . ? C31 C30 C29 121.0(8) . . ? C31 C30 H30 119.5 . . ? C29 C30 H30 119.5 . . ? C30 C31 C32 120.3(8) . . ? C30 C31 H31 119.8 . . ? C32 C31 H31 119.8 . . ? C33 C32 C31 118.2(8) . . ? C33 C32 C35 120.4(7) . . ? C31 C32 C35 121.4(7) . . ? C34 C33 C32 121.1(8) . . ? C34 C33 H33 119.5 . . ? C32 C33 H33 119.5 . . ? C33 C34 C29 119.4(8) . . ? C33 C34 H34 120.3 . . ? C29 C34 H34 120.3 . . ? C36 C35 O4 111.9(8) . . ? C36 C35 C32 132.9(8) . . ? O4 C35 C32 115.2(7) . . ? C35 C36 C37 106.7(8) . . ? C35 C36 C43 128.5(8) . . ? C37 C36 C43 124.7(8) . . ? C42 C37 C38 120.5(8) . . ? C42 C37 C36 105.2(8) . . ? C38 C37 C36 134.3(9) . . ? C39 C38 C37 116.5(9) . . ? C39 C38 H38 121.7 . . ? C37 C38 H38 121.7 . . ? C40 C39 C38 120.1(10) . . ? C40 C39 H39 120.0 . . ? C38 C39 H39 120.0 . . ? C39 C40 C41 125.4(10) . . ? C39 C40 H40 117.3 . . ? C41 C40 H40 117.3 . . ? C42 C41 C40 112.2(10) . . ? C42 C41 H41 123.9 . . ? C40 C41 H41 123.9 . . ? C37 C42 C41 125.1(10) . . ? C37 C42 O4 111.3(8) . . ? C41 C42 O4 123.6(10) . . ? C45 C43 C44 120.7(8) . . ? C45 C43 C36 123.9(7) . . ? C44 C43 C36 115.2(6) . . ? N2 C44 C43 176.0(8) . . ? C43 C45 O5 115.2(7) . . ? C43 C45 C46 129.0(8) . . ? O5 C45 C46 115.8(6) . . ? C47 C46 C51 118.4(8) . . ? C47 C46 C45 122.6(7) . . ? C51 C46 C45 119.0(8) . . ? C46 C47 C48 121.0(8) . . ? C46 C47 H47 119.5 . . ? C48 C47 H47 119.5 . . ? C49 C48 C47 120.7(8) . . ? C49 C48 H48 119.7 . . ? C47 C48 H48 119.7 . . ? C48 C49 C50 119.1(8) . . ? C48 C49 H49 120.5 . . ? C50 C49 H49 120.5 . . ? C51 C50 C49 119.9(8) . . ? C51 C50 H50 120.1 . . ? C49 C50 H50 120.1 . . ? C50 C51 C46 121.0(8) . . ? C50 C51 H51 119.5 . . ? C46 C51 H51 119.5 . . ? O6 C52 O5 120.3(8) . . ? O6 C52 C53 126.9(9) . . ? O5 C52 C53 112.8(7) . . ? C55 C53 C54 104.2(14) . . ? C55 C53 C52 112.7(8) . . ? C54 C53 C52 106.6(9) . . ? C55 C53 C56 107.0(9) . . ? C54 C53 C56 115.6(14) . . ? C52 C53 C56 110.7(8) . . ? C55 C53 C54' 127(2) . . ? C54 C53 C54' 28.5(18) . . ? C52 C53 C54' 107.1(15) . . ? C56 C53 C54' 90(3) . . ? C53 C54 H54A 109.5 . . ? C53 C54 H54B 109.4 . . ? H54A C54 H54B 109.5 . . ? C53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C53 C54' H54D 109.6 . . ? C53 C54' H54E 109.4 . . ? H54D C54' H54E 109.5 . . ? C53 C54' H54F 109.5 . . ? H54D C54' H54F 109.5 . . ? H54E C54' H54F 109.5 . . ? C53 C55 H55A 109.5 . . ? C53 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? C53 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? C53 C56 H56A 109.5 . . ? C53 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C53 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? C14 O1 C7 106.2(6) . . ? C24 O2 C17 115.9(6) . . ? C35 O4 C42 104.9(7) . . ? C52 O5 C45 117.1(6) . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.950 _refine_diff_density_min -0.736 _refine_diff_density_rms 0.098 _database_code_depnum_ccdc_archive 'CCDC 881553' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a13131 #TrackingRef 'a13131.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H22 Br2 O4' _chemical_formula_sum 'C36 H22 Br2 O4' _chemical_formula_weight 678.36 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' 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.6326(7) _cell_length_b 18.9665(8) _cell_length_c 9.2524(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.506(2) _cell_angle_gamma 90.00 _cell_volume 2893.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 2.842 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5487 _exptl_absorpt_correction_T_max 0.8710 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12941 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0606 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5013 _reflns_number_gt 3351 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0320P)^2^+2.8759P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5013 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0803 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.0977 _refine_ls_wR_factor_gt 0.0825 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3438(2) 0.0405(2) 0.3852(4) 0.0344(9) Uani 1 1 d . . . C2 C 0.4034(2) 0.0894(2) 0.4245(4) 0.0383(10) Uani 1 1 d . . . H2 H 0.3946 0.1271 0.4883 0.046 Uiso 1 1 calc R . . C3 C 0.4768(2) 0.0831(2) 0.3699(4) 0.0395(10) Uani 1 1 d . . . H3 H 0.5188 0.1162 0.3977 0.047 Uiso 1 1 calc R . . C4 C 0.4895(2) 0.0287(2) 0.2748(4) 0.0300(9) Uani 1 1 d . . . C5 C 0.4283(2) -0.0208(2) 0.2405(4) 0.0329(9) Uani 1 1 d . . . H5 H 0.4368 -0.0591 0.1781 0.039 Uiso 1 1 calc R . . C6 C 0.3558(2) -0.0152(2) 0.2959(4) 0.0366(10) Uani 1 1 d . . . H6 H 0.3145 -0.0494 0.2726 0.044 Uiso 1 1 calc R . . C7 C 0.5649(2) 0.0262(2) 0.2095(4) 0.0312(9) Uani 1 1 d . . . C8 C 0.6126(2) 0.0769(2) 0.1613(4) 0.0301(9) Uani 1 1 d . . . C9 C 0.6820(2) 0.0408(2) 0.1169(4) 0.0294(9) Uani 1 1 d . . . C10 C 0.6694(2) -0.0295(2) 0.1355(4) 0.0308(9) Uani 1 1 d . . . C11 C 0.7076(2) -0.0951(2) 0.0979(4) 0.0307(9) Uani 1 1 d . . . C12 C 0.6914(2) -0.1574(2) 0.1672(4) 0.0369(10) Uani 1 1 d . . . H12 H 0.6585 -0.1563 0.2437 0.044 Uiso 1 1 calc R . . C13 C 0.7221(2) -0.2207(2) 0.1271(5) 0.0428(11) Uani 1 1 d . . . H13 H 0.7098 -0.2629 0.1748 0.051 Uiso 1 1 calc R . . C14 C 0.7709(3) -0.2227(2) 0.0176(5) 0.0485(12) Uani 1 1 d . . . H14 H 0.7925 -0.2664 -0.0098 0.058 Uiso 1 1 calc R . . C15 C 0.7882(3) -0.1617(2) -0.0520(5) 0.0490(12) Uani 1 1 d . . . H15 H 0.8218 -0.1634 -0.1275 0.059 Uiso 1 1 calc R . . C16 C 0.7571(2) -0.0977(2) -0.0127(4) 0.0406(10) Uani 1 1 d . . . H16 H 0.7695 -0.0557 -0.0611 0.049 Uiso 1 1 calc R . . C17 C 0.7483(2) 0.0786(2) 0.0547(4) 0.0307(9) Uani 1 1 d . . . C18 C 0.8347(2) 0.0679(2) 0.1162(4) 0.0347(9) Uani 1 1 d . . . C19 C 0.8587(2) 0.0258(2) 0.2352(4) 0.0432(11) Uani 1 1 d . . . H19 H 0.8192 0.0011 0.2807 0.052 Uiso 1 1 calc R . . C20 C 0.9403(3) 0.0190(3) 0.2893(5) 0.0589(13) Uani 1 1 d . . . H20 H 0.9565 -0.0101 0.3715 0.071 Uiso 1 1 calc R . . C21 C 0.9972(3) 0.0546(3) 0.2232(6) 0.0742(16) Uani 1 1 d . . . H21 H 1.0531 0.0492 0.2588 0.089 Uiso 1 1 calc R . . C22 C 0.9744(3) 0.0979(4) 0.1062(6) 0.0859(19) Uani 1 1 d . . . H22 H 1.0142 0.1230 0.0618 0.103 Uiso 1 1 calc R . . C23 C 0.8931(3) 0.1048(3) 0.0534(5) 0.0607(14) Uani 1 1 d . . . H23 H 0.8772 0.1352 -0.0269 0.073 Uiso 1 1 calc R . . C24 C 0.5896(2) 0.15212(19) 0.1525(4) 0.0285(9) Uani 1 1 d . . . C25 C 0.5128(2) 0.1709(2) 0.0850(4) 0.0350(10) Uani 1 1 d . . . H25 H 0.4794 0.1361 0.0334 0.042 Uiso 1 1 calc R . . C26 C 0.4843(2) 0.2390(2) 0.0913(4) 0.0426(11) Uani 1 1 d . . . H26 H 0.4314 0.2504 0.0458 0.051 Uiso 1 1 calc R . . C27 C 0.5322(3) 0.2901(2) 0.1634(4) 0.0458(11) Uani 1 1 d . . . H27 H 0.5122 0.3368 0.1693 0.055 Uiso 1 1 calc R . . C28 C 0.6098(2) 0.2733(2) 0.2275(4) 0.0412(10) Uani 1 1 d . . . H28 H 0.6436 0.3085 0.2768 0.049 Uiso 1 1 calc R . . C29 C 0.6374(2) 0.2058(2) 0.2193(4) 0.0309(9) Uani 1 1 d . . . C30 C 0.7316(2) 0.1656(2) 0.4157(4) 0.0347(9) Uani 1 1 d . . . C31 C 0.8190(2) 0.1683(2) 0.4759(4) 0.0319(9) Uani 1 1 d . . . C32 C 0.8425(2) 0.1385(2) 0.6101(4) 0.0423(11) Uani 1 1 d . . . H32 H 0.8034 0.1165 0.6614 0.051 Uiso 1 1 calc R . . C33 C 0.9230(2) 0.1406(2) 0.6708(4) 0.0438(11) Uani 1 1 d . . . H33 H 0.9396 0.1192 0.7627 0.053 Uiso 1 1 calc R . . C34 C 0.9785(2) 0.1737(2) 0.5976(4) 0.0384(10) Uani 1 1 d . . . C35 C 0.9572(2) 0.2026(2) 0.4631(5) 0.0481(12) Uani 1 1 d . . . H35 H 0.9967 0.2243 0.4123 0.058 Uiso 1 1 calc R . . C36 C 0.8762(2) 0.1998(2) 0.4019(4) 0.0420(11) Uani 1 1 d . . . H36 H 0.8602 0.2198 0.3084 0.050 Uiso 1 1 calc R . . O1 O 0.59803(14) -0.03904(13) 0.1921(3) 0.0318(6) Uani 1 1 d . . . O2 O 0.73041(16) 0.12133(15) -0.0426(3) 0.0436(7) Uani 1 1 d . . . O3 O 0.71878(14) 0.19270(13) 0.2790(3) 0.0351(6) Uani 1 1 d . . . O4 O 0.67899(16) 0.14249(18) 0.4783(3) 0.0527(8) Uani 1 1 d . . . Br1 Br 0.24161(3) 0.05278(3) 0.45307(5) 0.05526(16) Uani 1 1 d . . . Br2 Br 1.08740(3) 0.17786(3) 0.68831(6) 0.06491(19) 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 0.034(2) 0.038(2) 0.031(2) -0.0016(19) 0.0044(17) 0.0004(19) C2 0.040(2) 0.036(2) 0.040(2) -0.010(2) 0.0077(19) -0.005(2) C3 0.035(2) 0.038(2) 0.045(2) -0.009(2) 0.0033(19) -0.0081(19) C4 0.027(2) 0.028(2) 0.033(2) 0.0012(18) 0.0019(17) -0.0001(17) C5 0.038(2) 0.025(2) 0.035(2) -0.0010(18) 0.0014(18) -0.0022(18) C6 0.035(2) 0.036(2) 0.039(2) 0.002(2) 0.0009(18) -0.0087(19) C7 0.029(2) 0.027(2) 0.037(2) -0.0037(18) 0.0005(17) 0.0006(18) C8 0.027(2) 0.031(2) 0.031(2) -0.0019(18) -0.0033(16) 0.0022(17) C9 0.025(2) 0.033(2) 0.029(2) -0.0001(18) -0.0017(16) 0.0012(17) C10 0.025(2) 0.035(2) 0.032(2) -0.0004(19) 0.0023(17) 0.0020(17) C11 0.025(2) 0.032(2) 0.033(2) -0.0025(18) -0.0062(16) 0.0030(17) C12 0.037(2) 0.035(2) 0.037(2) -0.001(2) -0.0019(18) 0.0000(19) C13 0.042(3) 0.032(2) 0.050(3) 0.002(2) -0.010(2) 0.003(2) C14 0.043(3) 0.042(3) 0.056(3) -0.015(2) -0.007(2) 0.017(2) C15 0.048(3) 0.054(3) 0.046(3) -0.013(2) 0.007(2) 0.009(2) C16 0.041(2) 0.039(3) 0.042(2) -0.001(2) 0.0042(19) 0.003(2) C17 0.035(2) 0.032(2) 0.025(2) -0.0011(19) 0.0021(17) -0.0004(18) C18 0.030(2) 0.039(2) 0.035(2) -0.0018(19) 0.0039(18) 0.0006(19) C19 0.038(2) 0.043(3) 0.046(3) 0.005(2) -0.002(2) -0.001(2) C20 0.047(3) 0.060(3) 0.063(3) 0.006(3) -0.017(2) 0.006(3) C21 0.031(3) 0.099(5) 0.090(4) 0.006(4) -0.003(3) 0.003(3) C22 0.034(3) 0.133(6) 0.091(4) 0.030(4) 0.012(3) -0.013(3) C23 0.040(3) 0.089(4) 0.054(3) 0.019(3) 0.008(2) -0.006(3) C24 0.029(2) 0.026(2) 0.029(2) -0.0005(17) 0.0002(16) -0.0007(17) C25 0.032(2) 0.032(2) 0.038(2) -0.0050(19) -0.0063(17) -0.0026(19) C26 0.038(2) 0.035(2) 0.050(3) -0.003(2) -0.013(2) 0.007(2) C27 0.052(3) 0.028(2) 0.052(3) -0.003(2) -0.010(2) 0.009(2) C28 0.044(2) 0.030(2) 0.046(3) -0.006(2) -0.010(2) -0.0076(19) C29 0.030(2) 0.030(2) 0.031(2) 0.0025(18) -0.0032(17) -0.0001(18) C30 0.031(2) 0.038(2) 0.034(2) 0.0012(19) 0.0007(18) -0.0028(19) C31 0.029(2) 0.035(2) 0.032(2) -0.0017(19) 0.0017(16) 0.0008(18) C32 0.029(2) 0.058(3) 0.039(2) 0.009(2) 0.0046(18) -0.004(2) C33 0.035(2) 0.061(3) 0.033(2) 0.010(2) -0.0019(18) -0.002(2) C34 0.025(2) 0.044(3) 0.044(2) 0.004(2) -0.0028(18) -0.0041(19) C35 0.034(2) 0.056(3) 0.054(3) 0.014(2) 0.005(2) -0.008(2) C36 0.037(2) 0.048(3) 0.039(2) 0.011(2) -0.0017(19) -0.006(2) O1 0.0288(14) 0.0271(15) 0.0395(15) -0.0008(12) 0.0039(12) 0.0009(11) O2 0.0444(17) 0.0453(18) 0.0395(16) 0.0123(15) -0.0005(13) 0.0006(14) O3 0.0281(14) 0.0400(16) 0.0349(15) 0.0040(13) -0.0044(11) -0.0050(12) O4 0.0310(16) 0.083(2) 0.0433(17) 0.0171(17) 0.0020(13) -0.0064(16) Br1 0.0386(3) 0.0706(4) 0.0600(3) -0.0092(3) 0.0193(2) -0.0069(2) Br2 0.0290(2) 0.0851(4) 0.0756(4) 0.0200(3) -0.0122(2) -0.0101(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.372(5) . ? C1 C2 1.372(5) . ? C1 Br1 1.901(4) . ? C2 C3 1.386(5) . ? C2 H2 0.9500 . ? C3 C4 1.389(5) . ? C3 H3 0.9500 . ? C4 C5 1.391(5) . ? C4 C7 1.463(5) . ? C5 C6 1.375(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.357(5) . ? C7 O1 1.372(4) . ? C8 C9 1.446(5) . ? C8 C24 1.477(5) . ? C9 C10 1.364(5) . ? C9 C17 1.493(5) . ? C10 O1 1.371(4) . ? C10 C11 1.459(5) . ? C11 C12 1.389(5) . ? C11 C16 1.396(5) . ? C12 C13 1.373(5) . ? C12 H12 0.9500 . ? C13 C14 1.379(6) . ? C13 H13 0.9500 . ? C14 C15 1.373(6) . ? C14 H14 0.9500 . ? C15 C16 1.386(6) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O2 1.219(4) . ? C17 C18 1.488(5) . ? C18 C19 1.377(5) . ? C18 C23 1.386(5) . ? C19 C20 1.389(5) . ? C19 H19 0.9500 . ? C20 C21 1.371(7) . ? C20 H20 0.9500 . ? C21 C22 1.373(7) . ? C21 H21 0.9500 . ? C22 C23 1.382(6) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C29 1.387(5) . ? C24 C25 1.392(5) . ? C25 C26 1.379(5) . ? C25 H25 0.9500 . ? C26 C27 1.372(5) . ? C26 H26 0.9500 . ? C27 C28 1.386(5) . ? C27 H27 0.9500 . ? C28 C29 1.366(5) . ? C28 H28 0.9500 . ? C29 O3 1.415(4) . ? C30 O4 1.193(4) . ? C30 O3 1.357(4) . ? C30 C31 1.489(5) . ? C31 C32 1.374(5) . ? C31 C36 1.379(5) . ? C32 C33 1.383(5) . ? C32 H32 0.9500 . ? C33 C34 1.367(5) . ? C33 H33 0.9500 . ? C34 C35 1.364(5) . ? C34 Br2 1.896(4) . ? C35 C36 1.392(5) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.5(4) . . ? C6 C1 Br1 120.0(3) . . ? C2 C1 Br1 118.5(3) . . ? C1 C2 C3 119.0(4) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 120.6(4) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 118.6(3) . . ? C3 C4 C7 119.7(3) . . ? C5 C4 C7 121.6(3) . . ? C6 C5 C4 120.9(4) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C1 C6 C5 119.3(4) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C8 C7 O1 109.9(3) . . ? C8 C7 C4 132.9(4) . . ? O1 C7 C4 117.2(3) . . ? C7 C8 C9 106.3(3) . . ? C7 C8 C24 123.0(3) . . ? C9 C8 C24 130.7(3) . . ? C10 C9 C8 106.6(3) . . ? C10 C9 C17 130.6(3) . . ? C8 C9 C17 122.7(3) . . ? C9 C10 O1 109.4(3) . . ? C9 C10 C11 136.4(4) . . ? O1 C10 C11 113.8(3) . . ? C12 C11 C16 118.5(4) . . ? C12 C11 C10 119.9(3) . . ? C16 C11 C10 121.5(4) . . ? C13 C12 C11 121.2(4) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 119.9(4) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 120.1(4) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.4(4) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 120.0(4) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? O2 C17 C18 120.3(3) . . ? O2 C17 C9 118.8(3) . . ? C18 C17 C9 120.8(3) . . ? C19 C18 C23 118.8(4) . . ? C19 C18 C17 123.4(4) . . ? C23 C18 C17 117.7(4) . . ? C18 C19 C20 120.7(4) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C21 C20 C19 119.5(5) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C22 C21 C20 120.7(4) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C21 C22 C23 119.5(5) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C22 C23 C18 120.8(5) . . ? C22 C23 H23 119.6 . . ? C18 C23 H23 119.6 . . ? C29 C24 C25 116.8(3) . . ? C29 C24 C8 123.7(3) . . ? C25 C24 C8 119.2(3) . . ? C26 C25 C24 121.4(3) . . ? C26 C25 H25 119.3 . . ? C24 C25 H25 119.3 . . ? C27 C26 C25 120.1(4) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C26 C27 C28 119.7(4) . . ? C26 C27 H27 120.2 . . ? C28 C27 H27 120.2 . . ? C29 C28 C27 119.5(4) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C28 C29 C24 122.4(3) . . ? C28 C29 O3 117.0(3) . . ? C24 C29 O3 120.6(3) . . ? O4 C30 O3 123.8(3) . . ? O4 C30 C31 124.9(4) . . ? O3 C30 C31 111.2(3) . . ? C32 C31 C36 119.6(3) . . ? C32 C31 C30 118.3(3) . . ? C36 C31 C30 122.2(3) . . ? C31 C32 C33 120.1(4) . . ? C31 C32 H32 119.9 . . ? C33 C32 H32 119.9 . . ? C34 C33 C32 119.5(4) . . ? C34 C33 H33 120.3 . . ? C32 C33 H33 120.3 . . ? C35 C34 C33 121.7(4) . . ? C35 C34 Br2 120.4(3) . . ? C33 C34 Br2 117.9(3) . . ? C34 C35 C36 118.6(4) . . ? C34 C35 H35 120.7 . . ? C36 C35 H35 120.7 . . ? C31 C36 C35 120.5(4) . . ? C31 C36 H36 119.7 . . ? C35 C36 H36 119.7 . . ? C10 O1 C7 107.8(3) . . ? C30 O3 C29 117.1(3) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.859 _refine_diff_density_min -0.856 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 865912'