# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Aikawa, Haruo' _publ_contact_author_email yama@mail.pharm.tohoku.ac.jp _publ_section_title ; Synthesis of Chiral 1,8-Di(1-adamantyl)naphthalenes Stable at Ambient Temperatures ; loop_ _publ_author_name H.Aikawa Y.Takahira M.Yamaguchi # Attachment '- chiralnp.txt' data_100127 _database_code_depnum_ccdc_archive 'CCDC 777112' #TrackingRef '- chiralnp.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H52 Cl2 O4' _chemical_formula_weight 691.74 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' 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.664(4) _cell_length_b 12.144(4) _cell_length_c 14.023(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.547(4) _cell_angle_gamma 90.00 _cell_volume 1765.6(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9894 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 28.36 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9561 _exptl_absorpt_correction_T_max 0.9777 _exptl_absorpt_process_details ; SADABS (Sheldrick, 1997) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayered confocal mirror' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19483 _diffrn_reflns_av_R_equivalents 0.0466 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 27.49 _reflns_number_total 7942 _reflns_number_gt 7694 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SHELXD _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material ;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009) ; _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^)+(0.0990P)^2^+0.7158P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.039(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(9) _refine_ls_number_reflns 7942 _refine_ls_number_parameters 437 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1598 _refine_ls_wR_factor_gt 0.1578 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 0.7529(2) 0.06351(16) 0.17240(15) 0.0170(4) Uani 1 1 d . . . C2 C 0.8827(2) 0.04754(18) 0.18086(17) 0.0213(4) Uani 1 1 d . . . H1 H 0.9082 -0.0095 0.1431 0.026 Uiso 1 1 calc R . . C3 C 0.9798(2) 0.11008(19) 0.24167(17) 0.0226(4) Uani 1 1 d . . . H2 H 1.0675 0.0879 0.2532 0.027 Uiso 1 1 calc R . . C4 C 0.9464(2) 0.20326(18) 0.28399(16) 0.0190(4) Uani 1 1 d . . . C5 C 0.7679(2) 0.31727(17) 0.32506(14) 0.0161(4) Uani 1 1 d . . . C6 C 0.6431(2) 0.32760(17) 0.33115(15) 0.0184(4) Uani 1 1 d . . . H3 H 0.6110 0.3962 0.3478 0.022 Uiso 1 1 calc R . . C7 C 0.5627(2) 0.23475(18) 0.31240(16) 0.0195(4) Uani 1 1 d . . . H4 H 0.4786 0.2394 0.3240 0.023 Uiso 1 1 calc R . . C8 C 0.60096(19) 0.13732(17) 0.27789(15) 0.0161(4) Uani 1 1 d . . . C9 C 0.71912(19) 0.13835(16) 0.24363(14) 0.0151(4) Uani 1 1 d . . . C10 C 0.81277(19) 0.22191(16) 0.28453(14) 0.0153(4) Uani 1 1 d . . . C11 C 0.66274(19) 0.02904(17) 0.07281(15) 0.0161(4) Uani 1 1 d . . . C12 C 0.7068(2) 0.10025(18) -0.00666(17) 0.0222(4) Uani 1 1 d . . . H5 H 0.6966 0.1793 0.0072 0.027 Uiso 1 1 calc R . . H6 H 0.7993 0.0864 -0.0030 0.027 Uiso 1 1 calc R . . C13 C 0.6787(2) -0.09300(17) 0.04646(15) 0.0180(4) Uani 1 1 d . . . H7 H 0.7707 -0.1085 0.0497 0.022 Uiso 1 1 calc R . . H8 H 0.6508 -0.1410 0.0947 0.022 Uiso 1 1 calc R . . C14 C 0.5192(2) 0.05592(19) 0.06164(16) 0.0204(4) Uani 1 1 d . . . H9 H 0.4858 0.0137 0.1108 0.025 Uiso 1 1 calc R . . H10 H 0.5096 0.1353 0.0745 0.025 Uiso 1 1 calc R . . C15 C 0.6281(2) 0.0734(2) -0.11049(17) 0.0261(5) Uani 1 1 d . . . H11 H 0.6596 0.1196 -0.1592 0.031 Uiso 1 1 calc R . . C16 C 0.6448(2) -0.0484(2) -0.13239(17) 0.0272(5) Uani 1 1 d . . . H12 H 0.7368 -0.0642 -0.1292 0.033 Uiso 1 1 calc R . . H13 H 0.5944 -0.0663 -0.1993 0.033 Uiso 1 1 calc R . . C17 C 0.5981(2) -0.11900(18) -0.05707(16) 0.0222(4) Uani 1 1 d . . . H14 H 0.6085 -0.1986 -0.0718 0.027 Uiso 1 1 calc R . . C18 C 0.4558(2) -0.0952(2) -0.06226(16) 0.0243(4) Uani 1 1 d . . . H15 H 0.4259 -0.1405 -0.0132 0.029 Uiso 1 1 calc R . . H16 H 0.4031 -0.1144 -0.1281 0.029 Uiso 1 1 calc R . . C19 C 0.4397(2) 0.0276(2) -0.04167(16) 0.0228(4) Uani 1 1 d . . . H17 H 0.3467 0.0435 -0.0455 0.027 Uiso 1 1 calc R . . C20 C 0.4855(3) 0.0975(2) -0.11814(18) 0.0280(5) Uani 1 1 d . . . H18 H 0.4345 0.0793 -0.1848 0.034 Uiso 1 1 calc R . . H19 H 0.4734 0.1767 -0.1060 0.034 Uiso 1 1 calc R . . C21 C 0.5351(2) 0.03184(17) 0.30652(15) 0.0164(4) Uani 1 1 d . . . C22 C 0.5931(2) -0.07782(17) 0.28166(15) 0.0180(4) Uani 1 1 d . . . H20 H 0.5792 -0.0847 0.2096 0.022 Uiso 1 1 calc R . . H21 H 0.6872 -0.0779 0.3103 0.022 Uiso 1 1 calc R . . C23 C 0.3871(2) 0.03080(18) 0.26870(16) 0.0204(4) Uani 1 1 d . . . H22 H 0.3506 0.0994 0.2892 0.024 Uiso 1 1 calc R . . H23 H 0.3648 0.0281 0.1961 0.024 Uiso 1 1 calc R . . C24 C 0.5634(2) 0.03459(19) 0.42112(16) 0.0224(4) Uani 1 1 d . . . H24 H 0.6578 0.0342 0.4483 0.027 Uiso 1 1 calc R . . H25 H 0.5286 0.1036 0.4422 0.027 Uiso 1 1 calc R . . C25 C 0.5316(2) -0.17659(18) 0.32142(17) 0.0222(4) Uani 1 1 d . . . H26 H 0.5684 -0.2463 0.3014 0.027 Uiso 1 1 calc R . . C26 C 0.3849(2) -0.1749(2) 0.27868(18) 0.0258(5) Uani 1 1 d . . . H27 H 0.3665 -0.1794 0.2062 0.031 Uiso 1 1 calc R . . H28 H 0.3448 -0.2394 0.3030 0.031 Uiso 1 1 calc R . . C27 C 0.3281(2) -0.0690(2) 0.30923(17) 0.0242(4) Uani 1 1 d . . . H29 H 0.2326 -0.0691 0.2821 0.029 Uiso 1 1 calc R . . C28 C 0.3564(2) -0.0631(2) 0.42172(18) 0.0279(5) Uani 1 1 d . . . H30 H 0.3195 0.0054 0.4422 0.033 Uiso 1 1 calc R . . H31 H 0.3166 -0.1266 0.4476 0.033 Uiso 1 1 calc R . . C29 C 0.5028(2) -0.0645(2) 0.46223(16) 0.0256(5) Uani 1 1 d . . . H32 H 0.5223 -0.0592 0.5354 0.031 Uiso 1 1 calc R . . C30 C 0.5589(3) -0.1711(2) 0.43330(18) 0.0277(5) Uani 1 1 d . . . H33 H 0.5191 -0.2350 0.4588 0.033 Uiso 1 1 calc R . . H34 H 0.6531 -0.1733 0.4616 0.033 Uiso 1 1 calc R . . C31 C 1.1648(2) 0.2624(2) 0.3301(2) 0.0337(6) Uani 1 1 d . . . H35 H 1.1948 0.1972 0.3701 0.051 Uiso 1 1 calc R . . H36 H 1.2161 0.3265 0.3584 0.051 Uiso 1 1 calc R . . H37 H 1.1745 0.2502 0.2631 0.051 Uiso 1 1 calc R . . C32 C 0.87269(19) 0.47936(17) 0.29859(15) 0.0167(4) Uani 1 1 d . . . C33 C 0.9444(2) 0.57668(17) 0.34878(15) 0.0171(4) Uani 1 1 d . . . C34 C 1.0683(2) 0.55144(18) 0.42970(17) 0.0239(5) Uani 1 1 d . . . H38 H 1.1190 0.4915 0.4090 0.029 Uiso 1 1 calc R . . H39 H 1.0464 0.5304 0.4921 0.029 Uiso 1 1 calc R . . C35 C 1.1439(2) 0.66238(19) 0.44064(18) 0.0270(5) Uani 1 1 d . . . H40 H 1.1627 0.6892 0.5092 0.032 Uiso 1 1 calc R . . H41 H 1.2258 0.6548 0.4196 0.032 Uiso 1 1 calc R . . C36 C 1.0498(2) 0.73959(18) 0.37198(18) 0.0244(5) Uani 1 1 d . . . H42 H 1.0901 0.8085 0.3540 0.029 Uiso 1 1 calc R . . C37 C 0.9366(3) 0.75898(19) 0.4203(2) 0.0303(5) Uani 1 1 d . . . H43 H 0.9673 0.7751 0.4911 0.036 Uiso 1 1 calc R . . H44 H 0.8811 0.8203 0.3883 0.036 Uiso 1 1 calc R . . C38 C 0.8650(2) 0.64915(18) 0.40352(17) 0.0232(4) Uani 1 1 d . . . C39 C 0.9898(2) 0.66434(18) 0.28358(16) 0.0212(4) Uani 1 1 d . . . C40 C 0.8786(3) 0.7194(2) 0.20947(19) 0.0321(5) Uani 1 1 d . . . H45 H 0.9057 0.7925 0.1925 0.048 Uiso 1 1 calc R . . H46 H 0.8038 0.7267 0.2385 0.048 Uiso 1 1 calc R . . H47 H 0.8552 0.6741 0.1501 0.048 Uiso 1 1 calc R . . C41 C 1.0879(3) 0.6209(2) 0.2288(2) 0.0316(5) Uani 1 1 d . . . H48 H 1.0444 0.5719 0.1757 0.047 Uiso 1 1 calc R . . H49 H 1.1556 0.5800 0.2744 0.047 Uiso 1 1 calc R . . H50 H 1.1264 0.6829 0.2011 0.047 Uiso 1 1 calc R . . O1 O 1.03213(15) 0.28178(15) 0.32819(14) 0.0268(4) Uani 1 1 d . . . O2 O 0.85005(14) 0.40484(12) 0.36455(10) 0.0180(3) Uani 1 1 d . . . O3 O 0.83752(18) 0.46706(15) 0.21130(12) 0.0294(4) Uani 1 1 d . . . O4 O 0.7682(2) 0.62509(17) 0.42752(17) 0.0399(5) Uani 1 1 d . . . C42 C 0.9519(5) 0.3312(5) 0.0615(3) 0.0756(14) Uani 1 1 d . . . H51 H 0.9962 0.3828 0.1131 0.091 Uiso 1 1 calc R . . H52 H 0.8857 0.2913 0.0871 0.091 Uiso 1 1 calc R . . Cl1 Cl 1.06052(13) 0.23941(13) 0.03928(9) 0.0780(4) Uani 1 1 d . . . Cl2 Cl 0.87486(18) 0.4073(2) -0.04181(14) 0.1211(7) 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 0.0189(9) 0.0148(9) 0.0172(9) -0.0028(7) 0.0043(7) -0.0012(7) C2 0.0204(10) 0.0194(10) 0.0244(10) -0.0045(8) 0.0058(8) 0.0023(8) C3 0.0159(9) 0.0260(11) 0.0258(11) -0.0045(9) 0.0043(8) 0.0025(8) C4 0.0171(9) 0.0204(10) 0.0185(9) -0.0026(8) 0.0023(7) -0.0019(7) C5 0.0208(9) 0.0150(9) 0.0123(8) -0.0006(7) 0.0035(7) -0.0022(7) C6 0.0216(10) 0.0156(9) 0.0188(9) -0.0018(7) 0.0059(8) 0.0006(7) C7 0.0176(9) 0.0198(10) 0.0225(10) -0.0018(8) 0.0078(7) -0.0005(7) C8 0.0174(9) 0.0150(9) 0.0158(9) -0.0009(7) 0.0038(7) -0.0027(7) C9 0.0167(8) 0.0138(8) 0.0146(8) 0.0009(7) 0.0031(7) -0.0001(7) C10 0.0164(9) 0.0148(9) 0.0143(8) 0.0023(7) 0.0026(7) -0.0010(7) C11 0.0172(9) 0.0156(9) 0.0152(9) -0.0010(7) 0.0032(7) 0.0009(7) C12 0.0280(10) 0.0168(9) 0.0238(10) 0.0014(8) 0.0097(8) -0.0019(8) C13 0.0231(9) 0.0143(9) 0.0170(9) -0.0001(7) 0.0056(7) 0.0015(7) C14 0.0205(10) 0.0231(10) 0.0168(10) -0.0010(8) 0.0026(7) 0.0014(8) C15 0.0343(12) 0.0260(11) 0.0195(11) 0.0042(8) 0.0096(9) -0.0022(9) C16 0.0358(12) 0.0296(12) 0.0169(10) -0.0029(8) 0.0076(9) 0.0003(9) C17 0.0299(11) 0.0176(10) 0.0185(10) -0.0049(8) 0.0045(8) -0.0012(8) C18 0.0259(10) 0.0265(11) 0.0185(10) -0.0023(8) 0.0010(8) -0.0050(9) C19 0.0216(10) 0.0265(11) 0.0189(10) 0.0010(8) 0.0019(8) 0.0039(8) C20 0.0365(12) 0.0256(11) 0.0196(10) 0.0063(8) 0.0018(9) 0.0058(10) C21 0.0180(9) 0.0158(9) 0.0166(9) -0.0036(7) 0.0065(7) -0.0023(7) C22 0.0206(9) 0.0148(9) 0.0201(9) 0.0006(7) 0.0080(7) 0.0004(7) C23 0.0180(9) 0.0206(10) 0.0237(10) -0.0003(8) 0.0071(8) -0.0007(8) C24 0.0294(11) 0.0218(10) 0.0168(10) -0.0042(8) 0.0071(8) -0.0076(9) C25 0.0298(11) 0.0165(9) 0.0220(10) 0.0014(8) 0.0094(9) -0.0025(8) C26 0.0281(11) 0.0228(10) 0.0266(11) -0.0041(9) 0.0067(9) -0.0108(9) C27 0.0195(9) 0.0279(11) 0.0267(11) -0.0033(9) 0.0083(8) -0.0091(8) C28 0.0311(11) 0.0300(12) 0.0273(11) -0.0017(9) 0.0165(9) -0.0098(9) C29 0.0325(11) 0.0303(12) 0.0157(9) -0.0007(9) 0.0091(8) -0.0077(9) C30 0.0361(13) 0.0244(11) 0.0235(11) 0.0075(9) 0.0086(9) -0.0038(9) C31 0.0158(10) 0.0399(15) 0.0441(15) -0.0158(12) 0.0043(9) -0.0038(10) C32 0.0174(9) 0.0156(9) 0.0172(9) 0.0002(7) 0.0042(7) -0.0006(7) C33 0.0181(9) 0.0163(9) 0.0159(9) 0.0020(7) 0.0017(7) -0.0008(7) C34 0.0259(10) 0.0173(10) 0.0228(10) 0.0029(8) -0.0056(8) -0.0017(8) C35 0.0239(10) 0.0238(11) 0.0270(11) 0.0006(9) -0.0065(9) -0.0039(9) C36 0.0258(10) 0.0141(9) 0.0297(11) 0.0020(8) -0.0004(9) -0.0035(8) C37 0.0362(12) 0.0167(10) 0.0369(13) -0.0038(9) 0.0066(10) -0.0019(9) C38 0.0269(10) 0.0196(10) 0.0230(11) -0.0014(8) 0.0054(8) -0.0004(8) C39 0.0205(10) 0.0216(10) 0.0200(10) 0.0032(8) 0.0018(8) -0.0051(8) C40 0.0338(12) 0.0274(12) 0.0297(12) 0.0130(10) -0.0033(10) -0.0024(10) C41 0.0285(11) 0.0381(14) 0.0305(12) -0.0008(10) 0.0117(10) -0.0061(10) O1 0.0148(7) 0.0277(8) 0.0364(9) -0.0121(7) 0.0031(6) -0.0027(6) O2 0.0234(7) 0.0146(7) 0.0148(7) -0.0010(5) 0.0019(5) -0.0042(6) O3 0.0379(9) 0.0316(9) 0.0157(8) -0.0004(6) 0.0004(7) -0.0137(7) O4 0.0401(11) 0.0315(10) 0.0570(13) -0.0041(9) 0.0294(10) -0.0006(8) C42 0.093(3) 0.086(3) 0.051(2) -0.015(2) 0.025(2) -0.030(3) Cl1 0.0905(8) 0.0934(8) 0.0604(6) -0.0071(6) 0.0387(6) -0.0231(7) Cl2 0.1027(11) 0.177(2) 0.0935(11) 0.0490(12) 0.0433(9) 0.0256(12) _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 C2 1.375(3) . ? C1 C9 1.457(3) . ? C1 C11 1.556(3) . ? C2 C3 1.400(3) . ? C2 H1 0.9500 . ? C3 C4 1.363(3) . ? C3 H2 0.9500 . ? C4 O1 1.365(3) . ? C4 C10 1.445(3) . ? C5 C6 1.359(3) . ? C5 O2 1.407(2) . ? C5 C10 1.422(3) . ? C6 C7 1.404(3) . ? C6 H3 0.9500 . ? C7 C8 1.376(3) . ? C7 H4 0.9500 . ? C8 C9 1.450(3) . ? C8 C21 1.558(3) . ? C9 C10 1.445(3) . ? C11 C14 1.537(3) . ? C11 C13 1.546(3) . ? C11 C12 1.567(3) . ? C12 C15 1.535(3) . ? C12 H5 0.9900 . ? C12 H6 0.9900 . ? C13 C17 1.536(3) . ? C13 H7 0.9900 . ? C13 H8 0.9900 . ? C14 C19 1.536(3) . ? C14 H9 0.9900 . ? C14 H10 0.9900 . ? C15 C20 1.528(4) . ? C15 C16 1.531(3) . ? C15 H11 1.0000 . ? C16 C17 1.531(3) . ? C16 H12 0.9900 . ? C16 H13 0.9900 . ? C17 C18 1.530(3) . ? C17 H14 1.0000 . ? C18 C19 1.537(3) . ? C18 H15 0.9900 . ? C18 H16 0.9900 . ? C19 C20 1.534(3) . ? C19 H17 1.0000 . ? C20 H18 0.9900 . ? C20 H19 0.9900 . ? C21 C22 1.542(3) . ? C21 C23 1.543(3) . ? C21 C24 1.564(3) . ? C22 C25 1.533(3) . ? C22 H20 0.9900 . ? C22 H21 0.9900 . ? C23 C27 1.535(3) . ? C23 H22 0.9900 . ? C23 H23 0.9900 . ? C24 C29 1.541(3) . ? C24 H24 0.9900 . ? C24 H25 0.9900 . ? C25 C30 1.529(3) . ? C25 C26 1.539(3) . ? C25 H26 1.0000 . ? C26 C27 1.525(3) . ? C26 H27 0.9900 . ? C26 H28 0.9900 . ? C27 C28 1.537(3) . ? C27 H29 1.0000 . ? C28 C29 1.531(3) . ? C28 H30 0.9900 . ? C28 H31 0.9900 . ? C29 C30 1.521(4) . ? C29 H32 1.0000 . ? C30 H33 0.9900 . ? C30 H34 0.9900 . ? C31 O1 1.428(3) . ? C31 H35 0.9800 . ? C31 H36 0.9800 . ? C31 H37 0.9800 . ? C32 O3 1.203(3) . ? C32 O2 1.355(2) . ? C32 C33 1.491(3) . ? C33 C38 1.544(3) . ? C33 C39 1.553(3) . ? C33 C34 1.557(3) . ? C34 C35 1.559(3) . ? C34 H38 0.9900 . ? C34 H39 0.9900 . ? C35 C36 1.536(3) . ? C35 H40 0.9900 . ? C35 H41 0.9900 . ? C36 C37 1.534(4) . ? C36 C39 1.552(3) . ? C36 H42 1.0000 . ? C37 C38 1.527(3) . ? C37 H43 0.9900 . ? C37 H44 0.9900 . ? C38 O4 1.195(3) . ? C39 C41 1.530(3) . ? C39 C40 1.535(3) . ? C40 H45 0.9800 . ? C40 H46 0.9800 . ? C40 H47 0.9800 . ? C41 H48 0.9800 . ? C41 H49 0.9800 . ? C41 H50 0.9800 . ? C42 Cl1 1.688(6) . ? C42 Cl2 1.752(6) . ? C42 H51 0.9900 . ? C42 H52 0.9900 . ? 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 C2 C1 C9 115.75(18) . . ? C2 C1 C11 115.94(18) . . ? C9 C1 C11 125.68(17) . . ? C1 C2 C3 124.1(2) . . ? C1 C2 H1 117.9 . . ? C3 C2 H1 117.9 . . ? C4 C3 C2 118.97(19) . . ? C4 C3 H2 120.5 . . ? C2 C3 H2 120.5 . . ? C3 C4 O1 124.19(19) . . ? C3 C4 C10 119.40(19) . . ? O1 C4 C10 116.40(18) . . ? C6 C5 O2 115.75(18) . . ? C6 C5 C10 121.79(18) . . ? O2 C5 C10 122.42(18) . . ? C5 C6 C7 118.57(19) . . ? C5 C6 H3 120.7 . . ? C7 C6 H3 120.7 . . ? C8 C7 C6 122.56(19) . . ? C8 C7 H4 118.7 . . ? C6 C7 H4 118.7 . . ? C7 C8 C9 117.48(18) . . ? C7 C8 C21 115.32(17) . . ? C9 C8 C21 124.86(17) . . ? C10 C9 C8 116.62(17) . . ? C10 C9 C1 116.83(17) . . ? C8 C9 C1 126.54(18) . . ? C5 C10 C4 123.70(18) . . ? C5 C10 C9 117.68(17) . . ? C4 C10 C9 118.60(18) . . ? C14 C11 C13 109.98(17) . . ? C14 C11 C1 115.19(17) . . ? C13 C11 C1 113.14(16) . . ? C14 C11 C12 105.54(17) . . ? C13 C11 C12 106.91(16) . . ? C1 C11 C12 105.34(16) . . ? C15 C12 C11 111.65(18) . . ? C15 C12 H5 109.3 . . ? C11 C12 H5 109.3 . . ? C15 C12 H6 109.3 . . ? C11 C12 H6 109.3 . . ? H5 C12 H6 108.0 . . ? C17 C13 C11 110.76(17) . . ? C17 C13 H7 109.5 . . ? C11 C13 H7 109.5 . . ? C17 C13 H8 109.5 . . ? C11 C13 H8 109.5 . . ? H7 C13 H8 108.1 . . ? C19 C14 C11 111.39(18) . . ? C19 C14 H9 109.3 . . ? C11 C14 H9 109.3 . . ? C19 C14 H10 109.3 . . ? C11 C14 H10 109.3 . . ? H9 C14 H10 108.0 . . ? C20 C15 C16 109.4(2) . . ? C20 C15 C12 109.9(2) . . ? C16 C15 C12 109.38(19) . . ? C20 C15 H11 109.4 . . ? C16 C15 H11 109.4 . . ? C12 C15 H11 109.4 . . ? C15 C16 C17 109.32(19) . . ? C15 C16 H12 109.8 . . ? C17 C16 H12 109.8 . . ? C15 C16 H13 109.8 . . ? C17 C16 H13 109.8 . . ? H12 C16 H13 108.3 . . ? C18 C17 C16 109.93(19) . . ? C18 C17 C13 109.57(18) . . ? C16 C17 C13 109.68(18) . . ? C18 C17 H14 109.2 . . ? C16 C17 H14 109.2 . . ? C13 C17 H14 109.2 . . ? C17 C18 C19 109.08(18) . . ? C17 C18 H15 109.9 . . ? C19 C18 H15 109.9 . . ? C17 C18 H16 109.9 . . ? C19 C18 H16 109.9 . . ? H15 C18 H16 108.3 . . ? C20 C19 C14 109.86(19) . . ? C20 C19 C18 109.78(19) . . ? C14 C19 C18 109.48(18) . . ? C20 C19 H17 109.2 . . ? C14 C19 H17 109.2 . . ? C18 C19 H17 109.2 . . ? C15 C20 C19 108.62(19) . . ? C15 C20 H18 110.0 . . ? C19 C20 H18 110.0 . . ? C15 C20 H19 110.0 . . ? C19 C20 H19 110.0 . . ? H18 C20 H19 108.3 . . ? C22 C21 C23 110.33(16) . . ? C22 C21 C8 115.01(16) . . ? C23 C21 C8 113.87(17) . . ? C22 C21 C24 105.05(17) . . ? C23 C21 C24 106.78(17) . . ? C8 C21 C24 104.90(16) . . ? C25 C22 C21 111.41(17) . . ? C25 C22 H20 109.3 . . ? C21 C22 H20 109.3 . . ? C25 C22 H21 109.3 . . ? C21 C22 H21 109.3 . . ? H20 C22 H21 108.0 . . ? C27 C23 C21 110.75(18) . . ? C27 C23 H22 109.5 . . ? C21 C23 H22 109.5 . . ? C27 C23 H23 109.5 . . ? C21 C23 H23 109.5 . . ? H22 C23 H23 108.1 . . ? C29 C24 C21 111.77(17) . . ? C29 C24 H24 109.3 . . ? C21 C24 H24 109.3 . . ? C29 C24 H25 109.3 . . ? C21 C24 H25 109.3 . . ? H24 C24 H25 107.9 . . ? C30 C25 C22 110.16(18) . . ? C30 C25 C26 109.32(19) . . ? C22 C25 C26 109.30(18) . . ? C30 C25 H26 109.4 . . ? C22 C25 H26 109.4 . . ? C26 C25 H26 109.4 . . ? C27 C26 C25 109.65(18) . . ? C27 C26 H27 109.7 . . ? C25 C26 H27 109.7 . . ? C27 C26 H28 109.7 . . ? C25 C26 H28 109.7 . . ? H27 C26 H28 108.2 . . ? C26 C27 C23 109.73(18) . . ? C26 C27 C28 109.4(2) . . ? C23 C27 C28 110.11(18) . . ? C26 C27 H29 109.2 . . ? C23 C27 H29 109.2 . . ? C28 C27 H29 109.2 . . ? C29 C28 C27 108.55(18) . . ? C29 C28 H30 110.0 . . ? C27 C28 H30 110.0 . . ? C29 C28 H31 110.0 . . ? C27 C28 H31 110.0 . . ? H30 C28 H31 108.4 . . ? C30 C29 C28 110.0(2) . . ? C30 C29 C24 109.83(19) . . ? C28 C29 C24 109.4(2) . . ? C30 C29 H32 109.2 . . ? C28 C29 H32 109.2 . . ? C24 C29 H32 109.2 . . ? C29 C30 C25 108.57(19) . . ? C29 C30 H33 110.0 . . ? C25 C30 H33 110.0 . . ? C29 C30 H34 110.0 . . ? C25 C30 H34 110.0 . . ? H33 C30 H34 108.4 . . ? O1 C31 H35 109.5 . . ? O1 C31 H36 109.5 . . ? H35 C31 H36 109.5 . . ? O1 C31 H37 109.5 . . ? H35 C31 H37 109.5 . . ? H36 C31 H37 109.5 . . ? O3 C32 O2 123.28(19) . . ? O3 C32 C33 125.58(19) . . ? O2 C32 C33 111.14(17) . . ? C32 C33 C38 113.97(18) . . ? C32 C33 C39 117.48(17) . . ? C38 C33 C39 100.65(17) . . ? C32 C33 C34 116.19(17) . . ? C38 C33 C34 102.73(17) . . ? C39 C33 C34 103.62(17) . . ? C33 C34 C35 103.44(17) . . ? C33 C34 H38 111.1 . . ? C35 C34 H38 111.1 . . ? C33 C34 H39 111.1 . . ? C35 C34 H39 111.1 . . ? H38 C34 H39 109.0 . . ? C36 C35 C34 102.66(17) . . ? C36 C35 H40 111.2 . . ? C34 C35 H40 111.2 . . ? C36 C35 H41 111.2 . . ? C34 C35 H41 111.2 . . ? H40 C35 H41 109.1 . . ? C37 C36 C35 106.4(2) . . ? C37 C36 C39 102.88(18) . . ? C35 C36 C39 103.16(18) . . ? C37 C36 H42 114.4 . . ? C35 C36 H42 114.4 . . ? C39 C36 H42 114.4 . . ? C38 C37 C36 102.39(19) . . ? C38 C37 H43 111.3 . . ? C36 C37 H43 111.3 . . ? C38 C37 H44 111.3 . . ? C36 C37 H44 111.3 . . ? H43 C37 H44 109.2 . . ? O4 C38 C37 127.2(2) . . ? O4 C38 C33 127.7(2) . . ? C37 C38 C33 105.18(19) . . ? C41 C39 C40 108.7(2) . . ? C41 C39 C36 113.70(19) . . ? C40 C39 C36 113.1(2) . . ? C41 C39 C33 113.80(19) . . ? C40 C39 C33 113.53(18) . . ? C36 C39 C33 93.47(17) . . ? C39 C40 H45 109.5 . . ? C39 C40 H46 109.5 . . ? H45 C40 H46 109.5 . . ? C39 C40 H47 109.5 . . ? H45 C40 H47 109.5 . . ? H46 C40 H47 109.5 . . ? C39 C41 H48 109.5 . . ? C39 C41 H49 109.5 . . ? H48 C41 H49 109.5 . . ? C39 C41 H50 109.5 . . ? H48 C41 H50 109.5 . . ? H49 C41 H50 109.5 . . ? C4 O1 C31 116.66(18) . . ? C32 O2 C5 115.49(15) . . ? Cl1 C42 Cl2 113.9(3) . . ? Cl1 C42 H51 108.8 . . ? Cl2 C42 H51 108.8 . . ? Cl1 C42 H52 108.8 . . ? Cl2 C42 H52 108.8 . . ? H51 C42 H52 107.7 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.778 _refine_diff_density_min -0.757 _refine_diff_density_rms 0.113 _publ_section_references ;Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses. \nRele ; _chemical_absolute_configuration rmad #===END data_brtest _database_code_depnum_ccdc_archive 'CCDC 777113' #TrackingRef '- chiralnp.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H38 Br2 O2' _chemical_formula_weight 614.44 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 43 2 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, -z+1/2' '-x, y, -z' '-y, -x, -z+3/4' 'y, x, -z+1/4' 'y, -x, z+1/4' '-y, x, z+3/4' _cell_length_a 12.8196(4) _cell_length_b 12.8196(4) _cell_length_c 16.7042(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2745.20(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 18738 _cell_measurement_theta_min 3.18 _cell_measurement_theta_max 27.41 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 2.981 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6946 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed Xray tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device_type ? _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26043 _diffrn_reflns_av_R_equivalents 0.0596 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 27.41 _reflns_number_total 3132 _reflns_number_gt 2570 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material ;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009) ; _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^)+(0.0662P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.025(15) _refine_ls_number_reflns 3132 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1275 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 1.215 _refine_ls_restrained_S_all 1.215 _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 C1 C 0.3067(3) 0.1665(3) 0.6369(2) 0.0286(8) Uani 1 1 d . . . C2 C 0.3981(3) 0.1512(3) 0.6788(2) 0.0331(9) Uani 1 1 d . . . H1 H 0.4166 0.0827 0.6951 0.040 Uiso 1 1 calc R . . C3 C 0.4645(3) 0.2347(3) 0.6982(2) 0.0335(9) Uani 1 1 d . . . C4 C 0.4481(3) 0.3312(3) 0.6660(2) 0.0361(9) Uani 1 1 d . . . C5 C 0.3519(3) 0.3519(3) 0.6250 0.0309(12) Uani 1 2 d S . . C6 C 0.2724(3) 0.2724(3) 0.6250 0.0268(11) Uani 1 2 d S . . C7 C 0.2719(3) 0.0720(3) 0.5847(2) 0.0280(8) Uani 1 1 d . . . C8 C 0.1756(3) 0.0888(3) 0.5313(2) 0.0302(8) Uani 1 1 d . . . H2 H 0.1134 0.0998 0.5655 0.036 Uiso 1 1 calc R . . H3 H 0.1857 0.1522 0.4983 0.036 Uiso 1 1 calc R . . C9 C 0.2584(3) -0.0305(3) 0.6333(2) 0.0302(8) Uani 1 1 d . . . H4 H 0.3217 -0.0432 0.6658 0.036 Uiso 1 1 calc R . . H5 H 0.1985 -0.0233 0.6703 0.036 Uiso 1 1 calc R . . C10 C 0.3653(3) 0.0549(3) 0.5258(2) 0.0327(9) Uani 1 1 d . . . H6 H 0.3751 0.1186 0.4931 0.039 Uiso 1 1 calc R . . H7 H 0.4299 0.0434 0.5571 0.039 Uiso 1 1 calc R . . C11 C 0.1571(3) -0.0049(3) 0.4766(2) 0.0315(8) Uani 1 1 d . . . H8 H 0.0930 0.0080 0.4439 0.038 Uiso 1 1 calc R . . C12 C 0.1409(3) -0.1035(3) 0.5263(2) 0.0350(9) Uani 1 1 d . . . H9 H 0.1276 -0.1637 0.4906 0.042 Uiso 1 1 calc R . . H10 H 0.0797 -0.0947 0.5619 0.042 Uiso 1 1 calc R . . C13 C 0.2398(3) -0.1237(3) 0.5770(2) 0.0336(9) Uani 1 1 d . . . H11 H 0.2302 -0.1887 0.6094 0.040 Uiso 1 1 calc R . . C14 C 0.3340(3) -0.1369(3) 0.5208(2) 0.0362(9) Uani 1 1 d . . . H12 H 0.3978 -0.1495 0.5528 0.043 Uiso 1 1 calc R . . H13 H 0.3229 -0.1977 0.4853 0.043 Uiso 1 1 calc R . . C15 C 0.3476(3) -0.0379(3) 0.4703(2) 0.0346(9) Uani 1 1 d . . . H14 H 0.4091 -0.0463 0.4341 0.041 Uiso 1 1 calc R . . C16 C 0.2496(3) -0.0201(3) 0.4203(2) 0.0354(9) Uani 1 1 d . . . H15 H 0.2585 0.0425 0.3862 0.042 Uiso 1 1 calc R . . H16 H 0.2370 -0.0809 0.3850 0.042 Uiso 1 1 calc R . . C17 C 0.6054(4) 0.4111(6) 0.6253(5) 0.092(2) Uani 1 1 d . . . H17 H 0.6387 0.3422 0.6242 0.138 Uiso 1 1 calc R . . H18 H 0.6562 0.4634 0.6429 0.138 Uiso 1 1 calc R . . H19 H 0.5806 0.4288 0.5715 0.138 Uiso 1 1 calc R . . O1 O 0.5190(3) 0.4093(3) 0.6796(2) 0.0559(9) Uani 1 1 d . . . Br1 Br 0.58339(4) 0.20512(4) 0.76148(3) 0.05097(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 0.0222(19) 0.028(2) 0.0351(18) 0.0010(15) 0.0028(15) -0.0001(15) C2 0.030(2) 0.031(2) 0.038(2) 0.0030(16) -0.0007(16) 0.0042(17) C3 0.030(2) 0.033(2) 0.037(2) -0.0037(16) 0.0027(16) -0.0043(17) C4 0.029(2) 0.038(2) 0.042(2) 0.0007(18) -0.0033(17) -0.0100(17) C5 0.0280(18) 0.0280(18) 0.037(3) 0.0003(17) -0.0003(17) -0.008(2) C6 0.0258(17) 0.0258(17) 0.029(2) -0.0009(14) 0.0009(14) -0.001(2) C7 0.0231(19) 0.0251(19) 0.0358(18) -0.0013(14) -0.0006(15) 0.0010(15) C8 0.0232(19) 0.028(2) 0.040(2) 0.0016(16) 0.0029(15) 0.0012(16) C9 0.025(2) 0.027(2) 0.0387(19) 0.0019(15) -0.0009(15) 0.0007(15) C10 0.025(2) 0.031(2) 0.042(2) -0.0043(16) 0.0020(16) -0.0005(15) C11 0.0308(19) 0.029(2) 0.034(2) -0.0016(16) -0.0048(15) 0.0030(17) C12 0.031(2) 0.031(2) 0.043(2) -0.0070(16) 0.0022(17) -0.0047(17) C13 0.033(2) 0.0228(19) 0.045(2) 0.0006(16) 0.0000(17) 0.0000(16) C14 0.033(2) 0.028(2) 0.048(2) -0.0054(17) 0.0014(18) 0.0023(17) C15 0.024(2) 0.031(2) 0.048(2) -0.0075(17) 0.0066(17) 0.0006(16) C16 0.032(2) 0.032(2) 0.042(2) -0.0055(17) 0.0007(16) -0.0029(17) C17 0.036(3) 0.105(6) 0.134(5) 0.064(5) -0.006(3) -0.025(3) O1 0.047(2) 0.049(2) 0.072(2) 0.0138(17) -0.0222(17) -0.0267(17) Br1 0.0371(3) 0.0542(3) 0.0615(3) 0.0034(2) -0.0174(2) -0.0023(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 C2 1.378(5) . ? C1 C6 1.441(5) . ? C1 C7 1.558(5) . ? C2 C3 1.405(6) . ? C2 H1 0.9500 . ? C3 C4 1.366(6) . ? C3 Br1 1.894(4) . ? C4 O1 1.370(5) . ? C4 C5 1.435(5) . ? C5 C4 1.435(5) 6_556 ? C5 C6 1.441(7) . ? C6 C1 1.441(5) 6_556 ? C7 C8 1.539(5) . ? C7 C9 1.555(5) . ? C7 C10 1.565(5) . ? C8 C11 1.529(5) . ? C8 H2 0.9900 . ? C8 H3 0.9900 . ? C9 C13 1.539(5) . ? C9 H4 0.9900 . ? C9 H5 0.9900 . ? C10 C15 1.525(5) . ? C10 H6 0.9900 . ? C10 H7 0.9900 . ? C11 C16 1.525(6) . ? C11 C12 1.526(6) . ? C11 H8 1.0000 . ? C12 C13 1.547(6) . ? C12 H9 0.9900 . ? C12 H10 0.9900 . ? C13 C14 1.538(6) . ? C13 H11 1.0000 . ? C14 C15 1.533(6) . ? C14 H12 0.9900 . ? C14 H13 0.9900 . ? C15 C16 1.527(6) . ? C15 H14 1.0000 . ? C16 H15 0.9900 . ? C16 H16 0.9900 . ? C17 O1 1.433(7) . ? C17 H17 0.9800 . ? C17 H18 0.9800 . ? C17 H19 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 C2 C1 C6 117.6(4) . . ? C2 C1 C7 114.7(3) . . ? C6 C1 C7 124.6(3) . . ? C1 C2 C3 121.6(4) . . ? C1 C2 H1 119.2 . . ? C3 C2 H1 119.2 . . ? C4 C3 C2 120.4(4) . . ? C4 C3 Br1 121.7(3) . . ? C2 C3 Br1 117.6(3) . . ? C3 C4 O1 119.6(4) . . ? C3 C4 C5 119.2(4) . . ? O1 C4 C5 121.0(4) . . ? C4 C5 C4 123.0(5) . 6_556 ? C4 C5 C6 118.5(3) . . ? C4 C5 C6 118.5(3) 6_556 . ? C5 C6 C1 116.8(2) . 6_556 ? C5 C6 C1 116.8(2) . . ? C1 C6 C1 126.5(5) 6_556 . ? C8 C7 C9 109.3(3) . . ? C8 C7 C1 116.4(3) . . ? C9 C7 C1 113.4(3) . . ? C8 C7 C10 105.6(3) . . ? C9 C7 C10 107.2(3) . . ? C1 C7 C10 104.0(3) . . ? C11 C8 C7 111.1(3) . . ? C11 C8 H2 109.4 . . ? C7 C8 H2 109.4 . . ? C11 C8 H3 109.4 . . ? C7 C8 H3 109.4 . . ? H2 C8 H3 108.0 . . ? C13 C9 C7 110.8(3) . . ? C13 C9 H4 109.5 . . ? C7 C9 H4 109.5 . . ? C13 C9 H5 109.5 . . ? C7 C9 H5 109.5 . . ? H4 C9 H5 108.1 . . ? C15 C10 C7 112.2(3) . . ? C15 C10 H6 109.2 . . ? C7 C10 H6 109.2 . . ? C15 C10 H7 109.2 . . ? C7 C10 H7 109.2 . . ? H6 C10 H7 107.9 . . ? C16 C11 C12 109.6(3) . . ? C16 C11 C8 110.4(3) . . ? C12 C11 C8 110.3(3) . . ? C16 C11 H8 108.8 . . ? C12 C11 H8 108.8 . . ? C8 C11 H8 108.8 . . ? C11 C12 C13 109.0(3) . . ? C11 C12 H9 109.9 . . ? C13 C12 H9 109.9 . . ? C11 C12 H10 109.9 . . ? C13 C12 H10 109.9 . . ? H9 C12 H10 108.3 . . ? C14 C13 C9 109.6(3) . . ? C14 C13 C12 109.2(3) . . ? C9 C13 C12 109.3(3) . . ? C14 C13 H11 109.6 . . ? C9 C13 H11 109.6 . . ? C12 C13 H11 109.6 . . ? C15 C14 C13 109.5(3) . . ? C15 C14 H12 109.8 . . ? C13 C14 H12 109.8 . . ? C15 C14 H13 109.8 . . ? C13 C14 H13 109.8 . . ? H12 C14 H13 108.2 . . ? C10 C15 C16 109.8(3) . . ? C10 C15 C14 109.2(3) . . ? C16 C15 C14 109.4(3) . . ? C10 C15 H14 109.5 . . ? C16 C15 H14 109.5 . . ? C14 C15 H14 109.5 . . ? C11 C16 C15 108.7(3) . . ? C11 C16 H15 109.9 . . ? C15 C16 H15 109.9 . . ? C11 C16 H16 109.9 . . ? C15 C16 H16 109.9 . . ? H15 C16 H16 108.3 . . ? O1 C17 H17 109.5 . . ? O1 C17 H18 109.5 . . ? H17 C17 H18 109.5 . . ? O1 C17 H19 109.5 . . ? H17 C17 H19 109.5 . . ? H18 C17 H19 109.5 . . ? C4 O1 C17 114.8(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.912 _refine_diff_density_min -0.639 _refine_diff_density_rms 0.188 _publ_section_references ;Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses. \nRele ; _chemical_absolute_configuration ad