#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/06/2000645.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2000645 loop_ _publ_author_name 'Chiaroni, A.' 'Riche, C.' 'Benharref, A.' 'Chekroun, A.' 'Lavergne, J.-P.' _publ_contact_author ; Dr Claude Riche Institut de Chimie des Substances Naturelles C.N.R.S. 91198 Gif-sur-Yvette CEDEX France ; _publ_section_title ; Structure du 2\a,3\a,7\a,13\a-di\'epoxyhimachalane ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1720 _journal_page_last 1722 _journal_volume 48 _journal_year 1992 _chemical_formula_moiety 'C15 H24 O2' _chemical_formula_sum 'C15 H24 O2' _chemical_formula_weight 236.35 _chemical_name_systematic ; 2\a, 3\a,-7\a, 13\a-di\'epoxyhimachalane ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_type_scat_source International_Tables_Vol_IV_table_2.2B _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.548(2) _cell_length_b 9.685(2) _cell_length_c 21.282(8) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 28.65 _cell_measurement_theta_min 15.60 _cell_volume 1349.6(7) _computing_data_collection 'Nonius CAD4 Software 1987' _computing_data_reduction 'NONIUS (Riche, 1989)' _computing_molecular_graphics 'R3M (Riche, 1983) et ORTEP (Johnson, 1965)' _computing_publication_material 'ACTACIF (Riche, 1992)' _computing_structure_refinement 'SHELX76 (Sheldrick, 1976)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 293 _diffrn_measurement_device 'Nonius CAD4 diffractometer' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.064 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 4735 _diffrn_reflns_theta_max 66.75 _diffrn_reflns_theta_min 2.08 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.55 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.16 _exptl_crystal_description prism _exptl_crystal_F_000 520.00 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.28 _refine_diff_density_min -0.22 _refine_ls_abs_structure_details ; configuration absolue d\'eduite de celle de l'\acis-himachal\`ene ; _refine_ls_goodness_of_fit_obs 0.96 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 1384 _refine_ls_R_factor_obs 0.054 _refine_ls_shift/esd_max 0.14 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme ; w=1/[s^2^(F) + 0.0063F^2^] ; _refine_ls_wR_factor_obs 0.071 _reflns_number_observed 1390 _reflns_number_total 1408 _reflns_observed_criterion refl_observed_if_I_>_4.0_sigma(I) _[local]_cod_data_source_file pa1001.cif _[local]_cod_data_source_block diepoxyhimachalane _cod_database_code 2000645 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 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 -2 0 3 0 1 -1 0 10 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom C1 0.7620(3) 0.0776(2) 0.41210(10) 0.0420(10) Uani ? ? C2 0.8964(3) 0.1983(2) 0.43140(10) 0.0430(10) Uani ? ? C3 0.8646(3) 0.3395(2) 0.40850(10) 0.0470(10) Uani ? ? C4 0.6888(4) 0.3680(2) 0.36500(10) 0.0570(10) Uani ? ? C5 0.5302(3) 0.2533(3) 0.36520(10) 0.0580(10) Uani ? ? C6 0.6286(3) 0.1109(2) 0.35420(10) 0.0460(10) Uani ? ? C7 0.7316(3) 0.1010(2) 0.28970(10) 0.0500(10) Uani ? ? C8 0.9621(4) 0.1071(2) 0.28390(10) 0.0530(10) Uani ? ? C9 1.0667(4) -0.0277(2) 0.30220(10) 0.0590(10) Uani ? ? C10 1.0811(3) -0.0557(2) 0.37270(10) 0.0560(10) Uani ? ? C11 0.8808(3) -0.0624(2) 0.41080(10) 0.0490(10) Uani ? ? C12 1.0416(5) 0.4392(2) 0.40630(10) 0.065(2) Uani ? ? C13 0.6090(5) 0.1352(4) 0.23400(10) 0.075(2) Uani ? ? C14 0.7420(5) -0.1770(2) 0.3857(2) 0.068(2) Uani ? ? C15 0.9403(5) -0.0969(3) 0.47900(10) 0.067(2) Uani ? ? O16 0.8011(3) 0.3018(2) 0.47160(10) 0.0570(10) Uani ? ? O17 0.6472(3) -0.0060(2) 0.24890(10) 0.0710(10) Uani ? ? H1 0.675(4) 0.074(2) 0.4480(10) 0.046 Uiso ? ? H2 1.043(4) 0.183(3) 0.4460(10) 0.047 Uiso ? ? H4a 0.744(5) 0.376(3) 0.3230(10) 0.063 Uiso ? ? H4b 0.627(5) 0.450(4) 0.373(2) 0.063 Uiso ? ? H5a 0.428(5) 0.277(3) 0.3380(10) 0.064 Uiso ? ? H5b 0.455(5) 0.246(3) 0.4050(10) 0.064 Uiso ? ? H6 0.536(5) 0.045(3) 0.3510(10) 0.051 Uiso ? ? H8a 0.987(5) 0.127(3) 0.241(2) 0.058 Uiso ? ? H8b 1.017(4) 0.185(3) 0.3080(10) 0.058 Uiso ? ? H9a 1.194(5) -0.034(3) 0.2830(10) 0.065 Uiso ? ? H9b 0.995(5) -0.096(3) 0.2830(10) 0.065 Uiso ? ? H10a 1.189(4) 0.010(3) 0.3980(10) 0.061 Uiso ? ? H10b 1.160(4) -0.142(3) 0.3800(10) 0.061 Uiso ? ? H12a 1.077(5) 0.437(4) 0.372(2) 0.072 Uiso ? ? H12b 0.999(5) 0.536(4) 0.4250(10) 0.072 Uiso ? ? H12c 1.163(6) 0.411(3) 0.429(2) 0.072 Uiso ? ? H13a 0.454(6) 0.160(4) 0.241(2) 0.085 Uiso ? ? H13b 0.687(6) 0.167(4) 0.198(2) 0.085 Uiso ? ? H14a 0.722(5) -0.160(4) 0.342(2) 0.078 Uiso ? ? H14b 0.615(6) -0.186(4) 0.412(2) 0.078 Uiso ? ? H14c 0.836(5) -0.260(4) 0.395(2) 0.078 Uiso ? ? H15a 0.798(5) -0.114(4) 0.503(2) 0.075 Uiso ? ? H15b 1.026(5) -0.174(4) 0.4770(10) 0.075 Uiso ? ? H15c 1.039(6) -0.034(4) 0.499(2) 0.075 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 C1 0.0416(8) 0.0470(9) 0.0381(8) 0.0046(7) 0.0034(7) 0.0040(6) C2 0.0482(9) 0.0450(9) 0.0361(7) 0.0104(7) 0.0011(7) -0.0012(6) C3 0.0570(10) 0.0410(10) 0.0410(10) 0.0090(10) 0.0010(10) -0.0040(10) C4 0.0680(10) 0.0470(10) 0.0550(10) 0.0160(10) -0.0040(10) 0.0060(10) C5 0.0440(10) 0.0740(10) 0.0560(10) 0.0180(10) -0.0040(10) 0.0090(10) C6 0.0374(8) 0.0519(8) 0.0493(10) -0.0016(8) -0.0033(7) 0.0034(7) C7 0.0563(10) 0.0518(9) 0.0423(10) -0.0031(9) -0.0075(8) -0.0018(8) C8 0.0620(10) 0.0560(10) 0.0420(10) -0.0090(10) 0.0070(10) -0.0030(10) C9 0.0590(10) 0.0610(10) 0.0570(10) 0.0060(10) 0.0110(10) -0.0170(10) C10 0.0490(10) 0.0570(10) 0.0610(10) 0.0110(10) 0.0030(10) -0.0100(10) C11 0.0560(10) 0.0420(10) 0.0510(10) 0.0040(10) 0.0000(10) 0.0020(10) C12 0.082(2) 0.0440(10) 0.0700(10) -0.0010(10) -0.0020(10) -0.0060(10) C13 0.090(2) 0.084(2) 0.0520(10) -0.007(2) -0.0230(10) 0.0030(10) C14 0.077(2) 0.0450(10) 0.083(2) -0.0100(10) -0.0030(10) 0.0050(10) C15 0.0790(10) 0.0590(10) 0.0630(10) 0.0160(10) -0.0080(10) 0.0150(10) O16 0.0763(10) 0.0554(7) 0.0400(7) 0.0152(7) 0.0074(6) -0.0064(5) O17 0.0830(10) 0.0700(10) 0.0580(10) -0.0170(10) -0.0170(10) -0.0080(10) 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 _geom_bond_publ_flag C1 C2 . . 1.520(3) yes C1 C6 . . 1.545(3) yes C1 C11 . . 1.563(3) yes C2 C3 . . 1.467(2) yes C2 O16 . . 1.458(2) yes C3 C4 . . 1.504(3) yes C3 C12 . . 1.509(4) yes C3 O16 . . 1.451(2) yes C4 C5 . . 1.521(3) yes C5 C6 . . 1.540(3) yes C6 C7 . . 1.531(3) yes C7 C8 . . 1.515(3) yes C7 C13 . . 1.471(4) yes C7 O17 . . 1.462(3) yes C8 C9 . . 1.525(3) yes C9 C10 . . 1.528(3) yes C10 C11 . . 1.543(3) yes C11 C14 . . 1.531(3) yes C11 C15 . . 1.539(3) yes C13 O17 . . 1.426(4) yes C1 H1 . . 0.95(3) ? C2 H2 . . 1.02(3) ? C4 H4a . . 0.97(3) ? C4 H4b . . 0.91(4) ? C5 H5a . . 0.92(3) ? C5 H5b . . 0.99(3) ? C6 H6 . . 0.88(3) ? C8 H8a . . 0.95(3) ? C8 H8b . . 0.98(3) ? C9 H9a . . 0.93(3) ? C9 H9b . . 0.91(3) ? C10 H10a . . 1.09(3) ? C10 H10b . . 0.99(3) ? C12 H12a . . 0.77(4) ? C12 H12b . . 1.06(4) ? C12 H12c . . 0.97(4) ? C13 H13a . . 1.06(4) ? C13 H13b . . 0.98(4) ? C14 H14a . . 0.96(4) ? C14 H14b . . 1.01(4) ? C14 H14c . . 1.03(4) ? C15 H15a . . 1.07(3) ? C15 H15b . . 0.94(4) ? C15 H15c . . 0.99(4) ? 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 _geom_angle_publ_flag C2 C1 C6 . . . 112.50(10) yes C2 C1 C11 . . . 112.50(10) yes C2 C1 H1 . . . 99.5(15) yes C6 C1 C11 . . . 116.6(2) yes C6 C1 H1 . . . 107.7(15) yes C11 C1 H1 . . . 106.2(15) yes C1 C2 C3 . . . 123.0(2) yes C1 C2 O16 . . . 116.10(10) yes C1 C2 H2 . . . 120.8(15) yes C3 C2 O16 . . . 59.50(10) yes C3 C2 H2 . . . 111.9(15) yes O16 C2 H2 . . . 109.4(15) yes C2 C3 C4 . . . 119.0(2) yes C2 C3 C12 . . . 119.9(2) yes C2 C3 O16 . . . 60.00(10) yes C4 C3 C12 . . . 116.8(2) yes C4 C3 O16 . . . 113.4(2) yes C12 C3 O16 . . . 114.2(2) yes C3 C4 C5 . . . 112.8(2) yes C3 C4 H4a . . . 107.6(18) yes C3 C4 H4b . . . 112.(2) yes C5 C4 H4a . . . 108.2(18) yes C5 C4 H4b . . . 110.(2) yes H4a C4 H4b . . . 106.(3) yes C4 C5 C6 . . . 111.6(2) yes C4 C5 H5a . . . 108.4(19) yes C4 C5 H5b . . . 113.3(18) yes C6 C5 H5a . . . 115.6(19) yes C6 C5 H5b . . . 106.0(18) yes H5a C5 H5b . . . 102.(3) yes C1 C6 C5 . . . 107.6(2) yes C1 C6 C7 . . . 116.9(2) yes C1 C6 H6 . . . 107.6(18) yes C5 C6 C7 . . . 112.2(2) yes C5 C6 H6 . . . 111.9(18) yes C7 C6 H6 . . . 100.5(18) yes C6 C7 C8 . . . 120.6(2) yes C6 C7 C13 . . . 117.9(2) yes C6 C7 O17 . . . 114.3(2) yes C8 C7 C13 . . . 118.0(2) yes C8 C7 O17 . . . 110.8(2) yes C13 C7 O17 . . . 58.2(2) yes C7 C8 C9 . . . 113.2(2) yes C7 C8 H8a . . . 104.8(19) yes C7 C8 H8b . . . 110.6(17) yes C9 C8 H8a . . . 110.3(19) yes C9 C8 H8b . . . 111.4(17) yes H8a C8 H8b . . . 106.(3) yes C8 C9 C10 . . . 115.5(2) yes C8 C9 H9a . . . 110.(2) yes C8 C9 H9b . . . 106.(2) yes C10 C9 H9a . . . 111.(2) yes C10 C9 H9b . . . 110.(2) yes H9a C9 H9b . . . 103.(3) yes C9 C10 C11 . . . 118.1(2) yes C9 C10 H10a . . . 114.8(15) yes C9 C10 H10b . . . 109.1(18) yes C11 C10 H10a . . . 108.5(15) yes C11 C10 H10b . . . 109.1(18) yes H10a C10 H10b . . . 95.(2) yes C1 C11 C10 . . . 113.4(2) yes C1 C11 C14 . . . 109.8(2) yes C1 C11 C15 . . . 107.3(2) yes C10 C11 C14 . . . 110.6(2) yes C10 C11 C15 . . . 106.8(2) yes C14 C11 C15 . . . 108.7(2) yes C3 C12 H12a . . . 104.(3) yes C3 C12 H12b . . . 110.7(19) yes C3 C12 H12c . . . 116.(2) yes H12a C12 H12b . . . 118.(4) yes H12a C12 H12c . . . 103.(4) yes H12b C12 H12c . . . 106.(3) yes C7 C13 O17 . . . 60.6(2) yes C7 C13 H13a . . . 117.(2) yes C7 C13 H13b . . . 115.(3) yes O17 C13 H13a . . . 111.(2) yes O17 C13 H13b . . . 113.(3) yes H13a C13 H13b . . . 123.(3) yes C11 C14 H14a . . . 107.(2) yes C11 C14 H14b . . . 111.(2) yes C11 C14 H14c . . . 99.(2) yes H14a C14 H14b . . . 117.(3) yes H14a C14 H14c . . . 114.(3) yes H14b C14 H14c . . . 108.(3) yes C11 C15 H15a . . . 105.4(18) yes C11 C15 H15b . . . 106.(2) yes C11 C15 H15c . . . 117.(2) yes H15a C15 H15b . . . 115.(3) yes H15a C15 H15c . . . 117.(3) yes H15b C15 H15c . . . 97.(3) yes C2 O16 C3 . . . 60.60(10) yes C7 O17 C13 . . . 61.2(2) yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C6 C1 C2 C3 14.90(10) yes C1 C2 C3 C4 1.20(10) yes C2 C3 C4 C5 16.70(10) yes C3 C4 C5 C6 -51.60(10) yes C4 C5 C6 C1 67.30(10) yes C5 C6 C1 C2 -46.80(10) yes C1 C2 C3 C12 -154.6(2) yes C1 C2 C3 O16 103.0(2) yes C11 C1 C6 C7 -51.80(10) yes C1 C6 C7 C8 -20.20(10) yes C6 C7 C8 C9 77.0(2) yes C7 C8 C9 C10 -76.4(2) yes C8 C9 C10 C11 58.6(2) yes C9 C10 C11 C1 -64.1(2) yes C10 C11 C1 C6 81.20(10) yes C5 C6 C7 C13 -53.8(2) yes C9 C8 C7 O17 -60.4(2) yes _journal_paper_doi 10.1107/S0108270192005316