data_2003361 _journal_name_full 'Acta Crystallographica' _journal_year 1995 _journal_volume C51 _journal_page_first 743 _journal_page_last 744 _publ_section_title ; (Z)-12-Hydroxy-14,15-dinorlabda-8(17),11-dien-13-one ; _chemical_formula_sum 'C18 H28 O2' _chemical_formula_weight 276.4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _symmetry_space_group_name_H-M 'P21' _cell_length_a 7.353(9) _cell_length_b 10.805(7) _cell_length_c 9.959(11) _cell_angle_alpha 90.00 _cell_angle_beta 93.2(1) _cell_angle_gamma 90.00 _cell_volume 790(2) _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 31 _exptl_absorpt_coefficient_mu 0.073 _cell_measurement_temperature 148(2) _exptl_crystal_description 'rectangular plate' _exptl_crystal_size_max 0.82 _exptl_crystal_size_mid 0.56 _exptl_crystal_size_min 0.20 _exptl_crystal_colour colourless _chemical_compound_source 'slow evaporation from hexane' _diffrn_measurement_device 'Nicolet R3m diffractometer' _diffrn_measurement_method '\w scans' _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_reflns_number 2983 _reflns_number_total 2983 _reflns_number_observed 2361 _reflns_observed_criterion >2sigma(I) _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_theta_max 32.49 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_obs 0.0517 _refine_ls_wR_factor_obs 0.1357 _refine_ls_wR_factor_all 0.1464 _refine_ls_goodness_of_fit_obs 1.020 _refine_ls_goodness_of_fit_all 0.973 _refine_ls_number_reflns 2983 _refine_ls_number_parameters 184 _refine_ls_hydrogen_treatment noref _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] _refine_ls_shift/esd_max 0.020 _refine_diff_density_max 0.244 _refine_diff_density_min -0.243 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag 'C' 'C' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.001 'H' 'H' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000 'O' 'O' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0106 0.006 _refine_ls_abs_structure_details 'inferred from preparation' _refine_ls_abs_structure_Flack 1.30(182) loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv O1 1 0.7576(3) 0.6839(3) 0.6587(2) 0.0434(5) HO1 1 0.7910(3) 0.7445(3) 0.6171(2) 0.050 O2 1 0.9975(3) 0.7165(3) 0.4826(2) 0.0374(5) C1 1 0.9081(3) 0.4926(3) 0.9822(2) 0.0245(4) H1A 1 1.0154(3) 0.4847(3) 0.9304(2) 0.050 H1B 1 0.8646(3) 0.5771(3) 0.9729(2) 0.050 C2 1 0.9611(3) 0.4671(3) 1.1304(2) 0.0270(4) H2A 1 1.0115(3) 0.3844(3) 1.1401(2) 0.050 H2B 1 1.0535(3) 0.5257(3) 1.1625(2) 0.050 C3 1 0.7945(3) 0.4788(3) 1.2138(2) 0.0266(4) H3A 1 0.7518(3) 0.5638(3) 1.2092(2) 0.050 H3B 1 0.8305(3) 0.4610(3) 1.3070(2) 0.050 C4 1 0.6363(3) 0.3930(3) 1.1689(2) 0.0203(4) C5 1 0.5933(2) 0.4082(3) 1.0141(2) 0.0170(3) H5 1 0.5462(2) 0.4928(3) 1.0040(2) 0.050 C6 1 0.4375(3) 0.3259(3) 0.9567(2) 0.0231(4) H6A 1 0.3344(3) 0.3330(3) 1.0129(2) 0.050 H6B 1 0.4770(3) 0.2402(3) 0.9584(2) 0.050 C7 1 0.3778(3) 0.3621(3) 0.8121(2) 0.0264(5) H7A 1 0.2907(3) 0.3020(3) 0.7752(2) 0.050 H7B 1 0.3181(3) 0.4422(3) 0.8122(2) 0.050 C8 1 0.5385(3) 0.3681(3) 0.7247(2) 0.0237(4) C9 1 0.6885(3) 0.4527(3) 0.7816(2) 0.0197(4) H9 1 0.6316(3) 0.5332(3) 0.7963(2) 0.050 C10 1 0.7600(2) 0.4044 0.9241(2) 0.0174(3) C11 1 0.8373(3) 0.4749(3) 0.6874(2) 0.0213(4) H11 1 0.9132(3) 0.4095(3) 0.6671(2) 0.050 C12 1 0.8646(3) 0.5851(3) 0.6315(2) 0.0224(4) C13 1 1.0032(3) 0.6136(3) 0.5339(2) 0.0231(4) C16 1 1.1478(3) 0.5228(3) 0.5024(2) 0.0274(5) H16A 1 1.0982(9) 0.4406(4) 0.5023(22) 0.050 H16B 1 1.2467(14) 0.5284(15) 0.5693(13) 0.050 H16C 1 1.1915(22) 0.5409(13) 0.4155(10) 0.050 C17 1 0.5465(4) 0.3016(3) 0.6135(3) 0.0354(6) H17A 1 0.4509(4) 0.2490(3) 0.5871(3) 0.050 H17B 1 0.6477(4) 0.3074(3) 0.5618(3) 0.050 C18 1 0.4705(3) 0.4353(3) 1.2435(2) 0.0275(5) H18A 1 0.3722(10) 0.3779(11) 1.2264(18) 0.050 H18B 1 0.4336(18) 0.5161(9) 1.2125(16) 0.050 H18C 1 0.5018(9) 0.4383(20) 1.3383(3) 0.050 C19 1 0.6801(3) 0.2596(3) 1.2123(2) 0.0268(4) H19A 1 0.7925(15) 0.2344(7) 1.1761(18) 0.050 H19B 1 0.5838(14) 0.2058(4) 1.1792(18) 0.050 H19C 1 0.6913(28) 0.2552(5) 1.3086(2) 0.050 C20 1 0.8414(3) 0.2745(3) 0.9087(2) 0.0235(4) H20A 1 0.7460(5) 0.2171(5) 0.8829(21) 0.050 H20B 1 0.8999(26) 0.2489(9) 0.9927(6) 0.050 H20C 1 0.9291(22) 0.2762(5) 0.8408(16) 0.050 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 O1 0.0517(12) 0.0153(9) 0.0324(10) 0.0238(9) 0.0141(9) 0.0581(12) O2 0.0421(10) 0.0014(8) 0.0173(9) 0.0277(9) 0.0134(8) 0.0441(11) C1 0.0166(9) -0.0040(8) 0.0047(8) 0.0260(10) 0.0013(8) 0.0314(10) C2 0.0190(9) -0.0078(9) -0.0001(8) 0.0313(11) -0.0003(9) 0.0306(10) C3 0.0244(10) -0.0040(9) 0.0012(8) 0.0285(11) -0.0028(9) 0.0269(10) C4 0.0178(8) 0.0005(7) 0.0043(7) 0.0208(9) 0.0033(7) 0.0227(9) C5 0.0140(7) 0.0006(7) 0.0039(6) 0.0163(8) 0.0027(7) 0.0211(8) C6 0.0176(9) -0.0042(8) 0.0052(7) 0.0264(10) 0.0033(8) 0.0257(9) C7 0.0165(9) -0.0017(9) 0.0018(8) 0.0360(12) 0.0012(9) 0.0267(10) C8 0.0187(9) 0.0008(8) 0.0019(7) 0.0288(10) 0.0031(8) 0.0237(9) C9 0.0159(8) 0.0036(7) 0.0065(7) 0.0196(9) 0.0033(7) 0.0242(9) C10 0.0122(7) 0.0009(7) 0.0046(6) 0.0155(8) 0.0019(7) 0.0247(8) C11 0.0189(8) 0.0043(8) 0.0072(7) 0.0210(9) 0.0003(8) 0.0247(9) C12 0.0215(9) 0.0029(8) 0.0076(8) 0.0207(9) 0.0010(8) 0.0257(9) C13 0.0216(9) -0.0017(8) 0.0061(8) 0.0246(10) 0.0023(8) 0.0235(10) C16 0.0230(10) 0.0010(9) 0.0118(8) 0.0305(11) 0.0017(9) 0.0299(11) C17 0.0317(12) -0.0012(11) 0.0013(10) 0.045(2) -0.0044(10) 0.0298(11) C18 0.0244(10) 0.0042(9) 0.0089(8) 0.0342(12) 0.0031(9) 0.0247(10) C19 0.0260(10) 0.0013(9) 0.0033(8) 0.0274(10) 0.0096(9) 0.0273(10) C20 0.0215(9) 0.0051(8) 0.0063(8) 0.0186(9) 0.0028(8) 0.0311(10)