# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1646 data_IAGO1 #----------- C20 H33 O Br -----------Compound 1 -------------------------- _audit_creation_date '1999-05-05' _audit_creation_method from_xtal_archive_file_using_CIFIO _audit_update_record '2000-03-16' _audit_conform_dict_name 'cif_core.dic' _audit_conform_dict_version '2.0.1' #--------------------------------------------------------------------------- _publ_requested_journal 'J. Chem. Soc. Chem. Commun.' _publ_contact_author ; Dr G\'erald Bernardinelli Laboratoire de Cristallographie Universit\'e de Gen\`eve 24, quai E. Ansermet CH - 1211 Gen\`eve 4 Switzerland ; _publ_contact_author_email gerald.bernardinelli@cryst.unige.ch _publ_contact_author_phone '41 (22) 702 62 02' _publ_contact_author_fax '41 (22) 702 61 08' loop_ _publ_author_name _publ_author_address 'Masayuki Kuniyoshi' ; Department of Chemistry, Biology and Marine Science University of the Ryukyus Nishihara Okinawa 903-0213 Japan ; 'Mong S. Marma' ; Department of Chemistry, Biology and Marine Science University of the Ryukyus Nishihara Okinawa 903-0213 Japan ; 'Tatsuo Higa' ; Department of Chemistry, Biology and Marine Science University of the Ryukyus Nishihara Okinawa 903-0213 Japan ; 'Bernardinelli, G\'erald' ; Laboratory of X-ray Crystallography University of Geneva 24, quai E. Ansermet CH - 1212 Geneva 4 Switzerland ; 'Charles W. Jefford' ; Department of Organic Chemistry University of Geneva 30, quai E. Ansermet CH - 1212 Geneva 4 Switzerland ; _publ_section_title ; 3-bromobarekoxide, an unusual diterpene from Laurenzia luzonensis ; _chemical_name_systematic ; 3-bromobarekoxide ; _chemical_formula_moiety 'C20 H33 O Br' _chemical_formula_sum 'C20 H33 O Br' _chemical_formula_weight 369.4 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 212121' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z _cell_length_a 7.6677(6) _cell_length_b 11.4190(10) _cell_length_c 21.0010(10) _cell_angle_alpha 90.00000 _cell_angle_beta 90.00000 _cell_angle_gamma 90.00000 _cell_volume 1838.8(3) _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_meas not_measured _diffrn_radiation_type 'CuK\a' _diffrn_radiation_wavelength 1.54183 _cell_measurement_reflns_used 38 _cell_measurement_theta_min 24 _cell_measurement_theta_max 26.5 _cell_measurement_temperature 200 _exptl_absorpt_coefficient_mu 3.029 _exptl_crystal_description prism _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_colour Colorless _diffrn_measurement_device_type Stoe_Stadi-4_4-circle_diffractometer _diffrn_measurement_method \w-2\q_scans _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min .446018 _exptl_absorpt_correction_T_max .526223 _diffrn_reflns_number 2757 _reflns_number_total 2248 _reflns_number_gt 2141 _reflns_threshold_expression 'refl observed if Fo > 4.0 \s(Fo)' _diffrn_reflns_theta_max 54.34 _diffrn_reflns_av_R_equivalents .022 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_standards_number 2 _diffrn_standards_interval_time 45 _diffrn_standards_decay_% 0 _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .031 _refine_ls_wR_factor_ref .030 _refine_ls_goodness_of_fit_ref 2.669 _refine_ls_number_reflns 2141 _refine_ls_number_parameters 255 _refine_ls_weighting_scheme calc _refine_ls_weighting_details '\w=1/[\s^2^(Fo)+0.00005(Fo^2^)]' _refine_ls_hydrogen_treatment ; Non -CH3 hydrogen atoms : observed and refined -CH3 hydrogen atoms: refined with restraints on bond lengths and bond angles and blocked in the last cycles ; _refine_ls_shift/su_max .458-3 _refine_diff_density_max .249 _refine_diff_density_min -.283 _refine_ls_extinction_method Zachariasen _refine_ls_extinction_coef 3949(300) _refine_ls_abs_structure_details Flack_xabs_refined _refine_ls_abs_structure_Flack .02(3) _computing_data_collection Stoe_Stadi-4 _computing_cell_refinement xtal_latcon _computing_data_reduction xtal_REFCAL_LSABS__SORTRF _computing_structure_solution multan_87 _computing_structure_refinement xtal_CRYLSQ _computing_molecular_graphics xtal_gx3 _computing_publication_material xtal_CIFIO loop_ _atom_type_symbol _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .017 .009 H Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 0 0 O Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .047 .032 Br Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 -.767 1.283 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type Br .56126(10) .15848(7) .41464(4) .0622(5) 1.00000 Uani O .2154(6) .9787(4) .24617(18) .053(3) 1.00000 Uani C1 .3244(7) .6727(6) .3462(3) .034(4) 1.00000 Uani C2 .3476(8) .5585(5) .3885(3) .034(4) 1.00000 Uani C3 .2688(9) .4535(6) .3514(3) .041(4) 1.00000 Uani C4 .3148(8) .3335(7) .3802(3) .046(4) 1.00000 Uani C5 .5091(8) .3205(6) .3856(3) .044(4) 1.00000 Uani C6 .6031(7) .4125(5) .4250(3) .037(4) 1.00000 Uani C7 .5464(9) .5335(5) .3944(3) .038(4) 1.00000 Uani C8 .6428(8) .6377(6) .4224(3) .043(4) 1.00000 Uani C9 .6229(8) .7422(6) .3782(4) .042(4) 1.00000 Uani C10 .4370(8) .7801(5) .3670(3) .038(4) 1.00000 Uani C11 .4432(9) .8722(5) .3120(3) .042(4) 1.00000 Uani C12 .2887(9) .9531(6) .3091(3) .043(4) 1.00000 Uani C13 .1153(8) .9110(6) .2922(3) .042(4) 1.00000 Uani C14 .0937(10) .7829(6) .2762(3) .045(4) 1.00000 Uani C15 .1308(8) .7011(6) .3333(3) .040(4) 1.00000 Uani C16 .2498(8) .5697(6) .4524(3) .043(4) 1.00000 Uani C17 .7990(8) .3983(5) .4164(3) .050(4) 1.00000 Uani C18 .5602(9) .4016(5) .4967(3) .046(4) 1.00000 Uani C19 .3652(7) .8416(6) .4268(3) .045(4) 1.00000 Uani C20 -.0404(9) .9731(6) .3187(3) .055(4) 1.00000 Uani H1 .367(7) .651(5) .305(3) .05000 1.00000 Uiso H31 .133(8) .453(5) .350(3) .05000 1.00000 Uiso H32 .311(8) .459(5) .306(3) .05000 1.00000 Uiso H41 .262(7) .329(5) .424(3) .05000 1.00000 Uiso H42 .273(8) .272(5) .353(3) .05000 1.00000 Uiso H5 .570(7) .324(5) .343(3) .05000 1.00000 Uiso H7 .585(8) .532(5) .349(3) .05000 1.00000 Uiso H81 .596(7) .655(5) .467(3) .05000 1.00000 Uiso H82 .764(8) .617(5) .429(3) .05000 1.00000 Uiso H91 .670(8) .808(5) .396(3) .05000 1.00000 Uiso H92 .677(8) .722(5) .335(3) .05000 1.00000 Uiso H111 .548(8) .927(5) .318(3) .05000 1.00000 Uiso H112 .464(7) .834(5) .271(3) .05000 1.00000 Uiso H12 .290(9) 1.014(6) .337(3) .05000 1.00000 Uiso H141 -.033(8) .774(5) .261(3) .05000 1.00000 Uiso H142 .181(8) .749(5) .240(3) .05000 1.00000 Uiso H151 .063(8) .732(5) .369(3) .05000 1.00000 Uiso H152 .068(8) .628(5) .322(3) .05000 1.00000 Uiso H161 .32738 .61682 .48622 .05000 1.00000 Uiso H162 .13423 .61360 .44511 .05000 1.00000 Uiso H163 .22134 .48468 .47023 .05000 1.00000 Uiso H171 .86679 .45335 .44640 .05000 1.00000 Uiso H172 .83558 .31002 .42583 .05000 1.00000 Uiso H173 .83231 .41705 .36992 .05000 1.00000 Uiso H181 .63143 .33014 .51599 .05000 1.00000 Uiso H182 .59437 .47895 .51985 .05000 1.00000 Uiso H183 .42324 .38689 .50288 .05000 1.00000 Uiso H191 .38671 .79073 .46707 .05000 1.00000 Uiso H192 .42624 .92062 .43282 .05000 1.00000 Uiso H193 .22816 .85648 .42232 .05000 1.00000 Uiso H201 -.14150 .96950 .28666 .05000 1.00000 Uiso H202 -.08008 .93322 .36057 .05000 1.00000 Uiso H203 -.00955 1.06107 .32890 .05000 1.00000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br .0655(5) .0421(4) .0791(5) -.0001(5) -.0187(5) .0003(4) O .055(3) .063(3) .042(3) -.006(3) -.001(3) .018(3) C1 .031(3) .042(4) .028(3) -.000(3) .003(3) .002(3) C2 .036(4) .038(4) .030(3) -.009(3) .003(3) -.003(3) C3 .037(4) .038(4) .047(4) -.002(3) -.007(3) -.007(3) C4 .042(4) .042(4) .055(4) -.008(4) -.009(3) -.003(4) C5 .046(4) .043(4) .043(4) .003(3) -.004(3) -.002(3) C6 .036(4) .041(4) .033(3) -.003(3) -.001(3) .001(3) C7 .033(4) .048(4) .032(4) -.010(4) .000(3) .002(3) C8 .033(4) .053(5) .044(4) -.012(3) -.007(3) .004(4) C9 .040(4) .041(4) .045(4) -.013(3) -.002(3) .003(4) C10 .034(4) .047(4) .033(3) -.008(4) .003(3) .003(3) C11 .041(4) .045(5) .040(3) -.012(4) .004(3) .007(3) C12 .046(5) .049(5) .035(4) -.006(4) .000(3) .007(3) C13 .041(5) .053(5) .032(4) -.004(4) -.001(3) .014(3) C14 .039(5) .056(4) .040(4) -.007(4) -.011(4) .001(4) C15 .034(4) .045(4) .040(4) -.004(3) .002(3) .003(3) C16 .039(4) .053(4) .036(3) -.003(4) .011(3) .003(3) C17 .041(4) .058(4) .051(4) -.002(3) -.004(4) .006(4) C18 .050(4) .051(4) .037(3) -.005(4) -.003(4) -.001(3) C19 .055(4) .042(4) .037(3) -.013(4) -.003(3) -.006(4) C20 .046(4) .059(5) .059(4) -.003(4) -.003(4) .013(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance Br C5 . . 1.989(7) O C12 . . 1.465(7) O C13 . . 1.456(7) C1 C2 . . 1.588(8) C1 C10 . . 1.562(8) C1 C15 . . 1.544(8) C1 H1 . . .97(5) C2 C3 . . 1.551(9) C2 C7 . . 1.555(9) C2 C16 . . 1.543(8) C3 C4 . . 1.539(10) C3 H31 . . 1.04(6) C3 H32 . . 1.01(6) C4 C5 . . 1.501(9) C4 H41 . . 1.01(5) C4 H42 . . .95(6) C5 C6 . . 1.520(8) C5 H5 . . 1.01(5) C6 C7 . . 1.585(8) C6 C17 . . 1.522(8) C6 C18 . . 1.546(7) C7 C8 . . 1.519(9) C7 H7 . . .99(6) C8 C9 . . 1.519(9) C8 H81 . . 1.02(5) C8 H82 . . .97(6) C9 C10 . . 1.508(9) C9 H91 . . .91(6) C9 H92 . . 1.03(6) C10 C11 . . 1.564(8) C10 C19 . . 1.540(8) C11 C12 . . 1.504(9) C11 H111 . . 1.02(6) C11 H112 . . .98(5) C12 C13 . . 1.458(9) C12 H12 . . .91(6) C13 C14 . . 1.509(9) C13 C20 . . 1.496(9) C14 C15 . . 1.546(9) C14 H141 . . 1.03(6) C14 H142 . . 1.09(6) C15 H151 . . .99(6) C15 H152 . . .99(6) C16 H161 . . 1.071(6) C16 H162 . . 1.030(6) C16 H163 . . 1.063(6) C17 H171 . . 1.031(6) C17 H172 . . 1.065(6) C17 H173 . . 1.031(6) C18 H181 . . 1.062(6) C18 H182 . . 1.042(6) C18 H183 . . 1.071(7) C19 H191 . . 1.039(6) C19 H192 . . 1.024(6) C19 H193 . . 1.069(6) C20 H201 . . 1.027(7) C20 H202 . . 1.037(7) C20 H203 . . 1.054(7) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle C12 O C13 . . . 59.9(4) C2 C1 C10 . . . 115.2(5) C2 C1 C15 . . . 112.2(5) C2 C1 H1 . . . 105(4) C10 C1 C15 . . . 114.6(5) C10 C1 H1 . . . 105(4) C15 C1 H1 . . . 103(3) C1 C2 C3 . . . 108.1(5) C1 C2 C7 . . . 107.8(5) C1 C2 C16 . . . 111.4(5) C3 C2 C7 . . . 106.3(5) C3 C2 C16 . . . 108.1(5) C7 C2 C16 . . . 115.0(5) C2 C3 C4 . . . 113.7(5) C2 C3 H31 . . . 114(3) C2 C3 H32 . . . 107(4) C4 C3 H31 . . . 104(3) C4 C3 H32 . . . 111(4) H31 C3 H32 . . . 107(5) C3 C4 C5 . . . 110.2(6) C3 C4 H41 . . . 108(4) C3 C4 H42 . . . 110(4) C5 C4 H41 . . . 109(3) C5 C4 H42 . . . 108(4) H41 C4 H42 . . . 112(5) Br C5 C4 . . . 108.3(5) Br C5 C6 . . . 112.3(4) Br C5 H5 . . . 102(4) C4 C5 C6 . . . 116.3(6) C4 C5 H5 . . . 113(3) C6 C5 H5 . . . 104(3) C5 C6 C7 . . . 104.5(5) C5 C6 C17 . . . 109.2(5) C5 C6 C18 . . . 112.0(5) C7 C6 C17 . . . 108.4(5) C7 C6 C18 . . . 114.1(5) C17 C6 C18 . . . 108.5(5) C2 C7 C6 . . . 117.4(5) C2 C7 C8 . . . 111.4(5) C2 C7 H7 . . . 103(4) C6 C7 C8 . . . 113.1(5) C6 C7 H7 . . . 107(4) C8 C7 H7 . . . 103(4) C7 C8 C9 . . . 109.2(5) C7 C8 H81 . . . 109(3) C7 C8 H82 . . . 109(3) C9 C8 H81 . . . 112(4) C9 C8 H82 . . . 112(3) H81 C8 H82 . . . 105(4) C8 C9 C10 . . . 114.5(5) C8 C9 H91 . . . 111(4) C8 C9 H92 . . . 109(3) C10 C9 H91 . . . 102(4) C10 C9 H92 . . . 108(4) H91 C9 H92 . . . 113(5) C1 C10 C9 . . . 109.9(5) C1 C10 C11 . . . 109.7(5) C1 C10 C19 . . . 112.9(5) C9 C10 C11 . . . 106.2(5) C9 C10 C19 . . . 110.0(5) C11 C10 C19 . . . 107.8(5) C10 C11 C12 . . . 114.8(5) C10 C11 H111 . . . 111(3) C10 C11 H112 . . . 111(4) C12 C11 H111 . . . 104(4) C12 C11 H112 . . . 111(3) H111 C11 H112 . . . 104(5) O C12 C11 . . . 117.5(5) O C12 C13 . . . 59.8(4) O C12 H12 . . . 116(4) C11 C12 C13 . . . 121.7(6) C11 C12 H12 . . . 116(4) C13 C12 H12 . . . 115(5) O C13 C12 . . . 60.4(4) O C13 C14 . . . 115.2(5) O C13 C20 . . . 114.5(5) C12 C13 C14 . . . 118.3(6) C12 C13 C20 . . . 118.7(6) C14 C13 C20 . . . 117.0(6) C13 C14 C15 . . . 113.2(5) C13 C14 H141 . . . 106(3) C13 C14 H142 . . . 115(3) C15 C14 H141 . . . 111(3) C15 C14 H142 . . . 103(3) H141 C14 H142 . . . 109(5) C1 C15 C14 . . . 116.1(5) C1 C15 H151 . . . 117(4) C1 C15 H152 . . . 109(4) C14 C15 H151 . . . 107(4) C14 C15 H152 . . . 104(3) H151 C15 H152 . . . 103(5) C2 C16 H161 . . . 110.4(5) C2 C16 H162 . . . 109.2(5) C2 C16 H163 . . . 109.3(5) H161 C16 H162 . . . 109.4(6) H161 C16 H163 . . . 109.9(5) H162 C16 H163 . . . 108.7(6) C6 C17 H171 . . . 111.1(5) C6 C17 H172 . . . 109.8(5) C6 C17 H173 . . . 109.6(5) H171 C17 H172 . . . 109.3(6) H171 C17 H173 . . . 109.1(6) H172 C17 H173 . . . 107.9(6) C6 C18 H181 . . . 108.9(5) C6 C18 H182 . . . 109.4(5) C6 C18 H183 . . . 109.8(5) H181 C18 H182 . . . 110.2(6) H181 C18 H183 . . . 109.8(5) H182 C18 H183 . . . 108.8(6) C10 C19 H191 . . . 110.6(5) C10 C19 H192 . . . 109.8(5) C10 C19 H193 . . . 110.6(5) H191 C19 H192 . . . 108.7(5) H191 C19 H193 . . . 108.5(5) H192 C19 H193 . . . 108.7(6) C13 C20 H201 . . . 109.9(6) C13 C20 H202 . . . 110.0(6) C13 C20 H203 . . . 110.4(6) H201 C20 H202 . . . 108.4(6) H201 C20 H203 . . . 110.0(6) H202 C20 H203 . . . 108.1(6) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion C13 O C12 C11 . . . . 112.5(7) C13 O C12 C13 . . . . .0(4) C13 O C12 H12 . . . . -105(5) C12 O C13 C12 . . . . -.0(4) C12 O C13 C14 . . . . -109.6(6) C12 O C13 C20 . . . . 110.4(6) C10 C1 C2 C3 . . . . -164.8(5) C10 C1 C2 C7 . . . . -50.4(6) C10 C1 C2 C16 . . . . 76.5(6) C15 C1 C2 C3 . . . . 61.6(6) C15 C1 C2 C7 . . . . 176.1(5) C15 C1 C2 C16 . . . . -57.0(6) H1 C1 C2 C3 . . . . -49(4) H1 C1 C2 C7 . . . . 65(4) H1 C1 C2 C16 . . . . -168(4) C2 C1 C10 C9 . . . . 47.7(6) C2 C1 C10 C11 . . . . 164.1(5) C2 C1 C10 C19 . . . . -75.6(6) C15 C1 C10 C9 . . . . -179.9(5) C15 C1 C10 C11 . . . . -63.5(6) C15 C1 C10 C19 . . . . 56.8(6) H1 C1 C10 C9 . . . . -68(4) H1 C1 C10 C11 . . . . 49(4) H1 C1 C10 C19 . . . . 169(4) C2 C1 C15 C14 . . . . -160.7(5) C2 C1 C15 H151 . . . . 72(4) C2 C1 C15 H152 . . . . -44(4) C10 C1 C15 C14 . . . . 65.5(7) C10 C1 C15 H151 . . . . -61(4) C10 C1 C15 H152 . . . . -178(3) H1 C1 C15 C14 . . . . -48(4) H1 C1 C15 H151 . . . . -175(5) H1 C1 C15 H152 . . . . 68(5) C1 C2 C3 C4 . . . . 168.2(5) C1 C2 C3 H31 . . . . -73(4) C1 C2 C3 H32 . . . . 45(4) C7 C2 C3 C4 . . . . 52.8(6) C7 C2 C3 H31 . . . . 171(4) C7 C2 C3 H32 . . . . -70(4) C16 C2 C3 C4 . . . . -71.2(6) C16 C2 C3 H31 . . . . 48(4) C16 C2 C3 H32 . . . . 166(4) C1 C2 C7 C6 . . . . -170.4(5) C1 C2 C7 C8 . . . . 57.0(6) C1 C2 C7 H7 . . . . -53(4) C3 C2 C7 C6 . . . . -54.7(6) C3 C2 C7 C8 . . . . 172.6(5) C3 C2 C7 H7 . . . . 63(4) C16 C2 C7 C6 . . . . 64.8(7) C16 C2 C7 C8 . . . . -67.8(7) C16 C2 C7 H7 . . . . -178(4) C1 C2 C16 H161 . . . . -83.0(6) C1 C2 C16 H162 . . . . 37.3(7) C1 C2 C16 H163 . . . . 156.1(5) C3 C2 C16 H161 . . . . 158.4(5) C3 C2 C16 H162 . . . . -81.3(6) C3 C2 C16 H163 . . . . 37.5(6) C7 C2 C16 H161 . . . . 39.9(7) C7 C2 C16 H162 . . . . 160.2(5) C7 C2 C16 H163 . . . . -81.0(6) C2 C3 C4 C5 . . . . -55.5(7) C2 C3 C4 H41 . . . . 63(4) C2 C3 C4 H42 . . . . -174(4) H31 C3 C4 C5 . . . . 180(3) H31 C3 C4 H41 . . . . -61(5) H31 C3 C4 H42 . . . . 61(5) H32 C3 C4 C5 . . . . 66(4) H32 C3 C4 H41 . . . . -175(5) H32 C3 C4 H42 . . . . -53(6) C3 C4 C5 Br . . . . -174.4(4) C3 C4 C5 C6 . . . . 58.0(7) C3 C4 C5 H5 . . . . -62(4) H41 C4 C5 Br . . . . 67(4) H41 C4 C5 C6 . . . . -60(4) H41 C4 C5 H5 . . . . 180(5) H42 C4 C5 Br . . . . -54(4) H42 C4 C5 C6 . . . . 178(4) H42 C4 C5 H5 . . . . 58(5) Br C5 C6 C7 . . . . 179.6(4) Br C5 C6 C17 . . . . 63.8(5) Br C5 C6 C18 . . . . -56.5(6) C4 C5 C6 C7 . . . . -54.8(7) C4 C5 C6 C17 . . . . -170.6(5) C4 C5 C6 C18 . . . . 69.1(7) H5 C5 C6 C7 . . . . 70(4) H5 C5 C6 C17 . . . . -46(4) H5 C5 C6 C18 . . . . -166(4) C5 C6 C7 C2 . . . . 54.6(6) C5 C6 C7 C8 . . . . -173.5(5) C5 C6 C7 H7 . . . . -60(4) C17 C6 C7 C2 . . . . 171.0(5) C17 C6 C7 C8 . . . . -57.1(6) C17 C6 C7 H7 . . . . 56(4) C18 C6 C7 C2 . . . . -68.0(6) C18 C6 C7 C8 . . . . 63.9(7) C18 C6 C7 H7 . . . . 177(4) C5 C6 C17 H171 . . . . -173.7(5) C5 C6 C17 H172 . . . . -52.6(7) C5 C6 C17 H173 . . . . 65.7(6) C7 C6 C17 H171 . . . . 73.0(6) C7 C6 C17 H172 . . . . -165.9(5) C7 C6 C17 H173 . . . . -47.6(6) C18 C6 C17 H171 . . . . -51.3(7) C18 C6 C17 H172 . . . . 69.7(6) C18 C6 C17 H173 . . . . -171.9(5) C5 C6 C18 H181 . . . . 76.8(7) C5 C6 C18 H182 . . . . -162.8(5) C5 C6 C18 H183 . . . . -43.4(7) C7 C6 C18 H181 . . . . -164.8(5) C7 C6 C18 H182 . . . . -44.3(7) C7 C6 C18 H183 . . . . 75.0(6) C17 C6 C18 H181 . . . . -43.9(7) C17 C6 C18 H182 . . . . 76.6(6) C17 C6 C18 H183 . . . . -164.1(5) C2 C7 C8 C9 . . . . -62.1(6) C2 C7 C8 H81 . . . . 61(4) C2 C7 C8 H82 . . . . 175(4) C6 C7 C8 C9 . . . . 163.1(5) C6 C7 C8 H81 . . . . -74(4) C6 C7 C8 H82 . . . . 40(4) H7 C7 C8 C9 . . . . 48(4) H7 C7 C8 H81 . . . . 170(5) H7 C7 C8 H82 . . . . -75(5) C7 C8 C9 C10 . . . . 59.8(7) C7 C8 C9 H91 . . . . 174(4) C7 C8 C9 H92 . . . . -61(4) H81 C8 C9 C10 . . . . -62(4) H81 C8 C9 H91 . . . . 53(5) H81 C8 C9 H92 . . . . 177(5) H82 C8 C9 C10 . . . . -179(4) H82 C8 C9 H91 . . . . -65(5) H82 C8 C9 H92 . . . . 60(5) C8 C9 C10 C1 . . . . -51.7(7) C8 C9 C10 C11 . . . . -170.3(5) C8 C9 C10 C19 . . . . 73.3(7) H91 C9 C10 C1 . . . . -171(4) H91 C9 C10 C11 . . . . 70(4) H91 C9 C10 C19 . . . . -46(4) H92 C9 C10 C1 . . . . 70(4) H92 C9 C10 C11 . . . . -48(4) H92 C9 C10 C19 . . . . -165(4) C1 C10 C11 C12 . . . . 82.9(6) C1 C10 C11 H111 . . . . -160(4) C1 C10 C11 H112 . . . . -45(4) C9 C10 C11 C12 . . . . -158.4(5) C9 C10 C11 H111 . . . . -41(4) C9 C10 C11 H112 . . . . 74(4) C19 C10 C11 C12 . . . . -40.5(7) C19 C10 C11 H111 . . . . 77(4) C19 C10 C11 H112 . . . . -168(4) C1 C10 C19 H191 . . . . 72.5(6) C1 C10 C19 H192 . . . . -167.6(5) C1 C10 C19 H193 . . . . -47.7(7) C9 C10 C19 H191 . . . . -50.7(7) C9 C10 C19 H192 . . . . 69.2(6) C9 C10 C19 H193 . . . . -170.9(5) C11 C10 C19 H191 . . . . -166.1(5) C11 C10 C19 H192 . . . . -46.2(7) C11 C10 C19 H193 . . . . 73.7(7) C10 C11 C12 O . . . . -137.7(5) C10 C11 C12 C13 . . . . -67.9(7) C10 C11 C12 H12 . . . . 80(5) H111 C11 C12 O . . . . 101(3) H111 C11 C12 C13 . . . . 171(3) H111 C11 C12 H12 . . . . -41(5) H112 C11 C12 O . . . . -10(4) H112 C11 C12 C13 . . . . 59(4) H112 C11 C12 H12 . . . . -153(6) O C12 C13 O . . . . .0(3) O C12 C13 C14 . . . . 104.4(6) O C12 C13 C20 . . . . -103.5(6) C11 C12 C13 O . . . . -105.5(6) C11 C12 C13 C14 . . . . -1.1(8) C11 C12 C13 C20 . . . . 151.0(6) H12 C12 C13 O . . . . 106(4) H12 C12 C13 C14 . . . . -149(4) H12 C12 C13 C20 . . . . 3(4) O C13 C14 C15 . . . . 133.3(6) O C13 C14 H141 . . . . -105(3) O C13 C14 H142 . . . . 15(4) C12 C13 C14 C15 . . . . 64.9(7) C12 C13 C14 H141 . . . . -174(3) C12 C13 C14 H142 . . . . -53(4) C20 C13 C14 C15 . . . . -87.7(7) C20 C13 C14 H141 . . . . 34(4) C20 C13 C14 H142 . . . . 154(4) O C13 C20 H201 . . . . 79.5(7) O C13 C20 H202 . . . . -161.2(5) O C13 C20 H203 . . . . -42.0(7) C12 C13 C20 H201 . . . . 147.8(6) C12 C13 C20 H202 . . . . -92.9(7) C12 C13 C20 H203 . . . . 26.3(8) C14 C13 C20 H201 . . . . -59.8(7) C14 C13 C20 H202 . . . . 59.5(7) C14 C13 C20 H203 . . . . 178.8(5) C13 C14 C15 C1 . . . . -82.0(7) C13 C14 C15 H151 . . . . 50(4) C13 C14 C15 H152 . . . . 158(4) H141 C14 C15 C1 . . . . 160(4) H141 C14 C15 H151 . . . . -69(5) H141 C14 C15 H152 . . . . 40(5) H142 C14 C15 C1 . . . . 43(4) H142 C14 C15 H151 . . . . 175(5) H142 C14 C15 H152 . . . . -77(5)