#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/35/2003599.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_2003599 loop_ _publ_author_name 'Chiaroni, A.' 'Riche, C.' 'Benharref, A.' 'El Jamili, H.' 'Lassaba, E.' _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 ; 2\a,3\a:7\b,13\b-Di\'epoxy-trans-himachalane ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1171 _journal_page_last 1173 _journal_paper_doi 10.1107/S0108270194014125 _journal_volume 51 _journal_year 1995 _chemical_compound_source ; from chemical synthesis ; _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\b,13\b-di\'epoxy-trans-himachalane. ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_type_scat_source 'International Tables for X-ray Crystallography (Tome IV, Tableau 2,2B)' _cell_angle_alpha 90.00 _cell_angle_beta 111.53(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 8.017(2) _cell_length_b 11.103(3) _cell_length_c 8.263(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 12.4 _cell_measurement_theta_min 8.3 _cell_volume 684.2(4) _computing_data_collection 'Philips PW1100/20 software (1974)' _computing_data_reduction 'PHIL (Riche, 1981)' _computing_molecular_graphics 'R3M (Riche,1983); 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 'Philips PW100 diffractometer' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1348 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.65 _diffrn_standards_decay_% 3 _diffrn_standards_interval_time 180 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.07 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.15 _exptl_crystal_description prism _exptl_crystal_F_000 260.00 _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.70 _exptl_crystal_size_min 0.50 _refine_diff_density_max 0.26 _refine_diff_density_min -0.22 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.04 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 153 _refine_ls_number_reflns 1111 _refine_ls_R_factor_obs 0.057 _refine_ls_shift/esd_max 0.02 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0012F^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.075 _reflns_number_observed 1111 _reflns_number_total 1268 _reflns_observed_criterion refl_observed_if_I_>_3.0_sigma(I) _cod_data_source_file pa1152.cif _cod_data_source_block diepo _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(F) + 0.0012F^2^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(F) + 0.0012F^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 684.2(3) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2003599 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,1/2+y,-z 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 C1 0.0430(15) -0.0008(13) 0.0237(13) 0.0285(14) 0.0017(14) 0.0487(15) C2 0.0449(16) -0.0030(14) 0.0209(14) 0.0389(17) -0.0077(16) 0.0588(18) C3 0.0447(16) -0.0006(15) 0.0112(14) 0.0418(18) -0.0017(17) 0.0587(19) C4 0.0532(20) 0.0127(16) 0.0251(19) 0.0492(22) -0.0004(19) 0.0765(26) C5 0.0658(22) 0.0125(20) 0.0435(19) 0.0612(24) -0.0044(21) 0.0760(25) C6 0.0515(17) -0.0020(15) 0.0270(14) 0.0393(17) -0.0025(15) 0.0516(18) C7 0.0793(22) 0.0047(22) 0.0409(18) 0.0637(23) 0.0017(20) 0.0520(18) C8 0.0900(28) 0.0010(26) 0.0189(19) 0.0864(35) 0.0165(21) 0.0461(19) C9 0.0664(22) 0.0179(22) 0.0186(17) 0.0787(29) 0.0261(24) 0.0628(22) C10 0.0455(16) 0.0048(19) 0.0220(16) 0.0675(24) 0.0169(22) 0.0699(21) C11 0.0456(15) 0.0044(16) 0.0305(13) 0.0481(19) 0.0083(18) 0.0564(17) C12 0.0684(26) 0.0190(22) 0.0039(20) 0.0734(30) 0.0022(22) 0.0669(27) C13 0.1107(35) 0.0002(29) 0.0700(29) 0.0807(35) 0.0189(28) 0.0906(33) C14 0.0818(29) 0.0248(23) 0.0520(24) 0.0686(31) 0.0017(23) 0.0840(30) C15 0.0585(21) -0.0086(20) 0.0331(18) 0.0694(25) 0.0197(21) 0.0683(25) O16 0.0464(13) -0.0089(12) 0.0151(12) 0.0471(14) -0.0024(17) 0.0958(18) O17 0.1176(23) 0.0193(25) 0.0713(18) 0.1183(31) 0.0110(23) 0.0771(18) 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 0.7137(4) 0.5470 0.2759(4) 0.042(3) Uani ? ? C2 0.8522(4) 0.5238(4) 0.4545(4) 0.051(3) Uani ? ? C3 0.9783(5) 0.4226(5) 0.4943(5) 0.053(3) Uani ? ? C4 0.9779(5) 0.3434(5) 0.3485(5) 0.064(4) Uani ? ? C5 0.9237(5) 0.4113(5) 0.1782(5) 0.071(5) Uani ? ? C6 0.7391(4) 0.4701(4) 0.1298(4) 0.050(3) Uani ? ? C7 0.6922(5) 0.5486(5) -0.0342(5) 0.068(4) Uani ? ? C8 0.4955(6) 0.5632(6) -0.1404(5) 0.079(5) Uani ? ? C9 0.3846(6) 0.6124(6) -0.0404(5) 0.074(5) Uani ? ? C10 0.3736(4) 0.5278(5) 0.1014(5) 0.065(4) Uani ? ? C11 0.5216(4) 0.5368(5) 0.2833(4) 0.052(3) Uani ? ? C12 1.0457(6) 0.3671(5) 0.6719(6) 0.076(5) Uani ? ? C13 0.8183(7) 0.6397(6) -0.0451(6) 0.097(7) Uani ? ? C14 0.4852(6) 0.6484(5) 0.3743(6) 0.081(6) Uani ? ? C15 0.5083(5) 0.4240(5) 0.3845(6) 0.069(5) Uani ? ? O16 1.0399(3) 0.5446(4) 0.4826(4) 0.069(3) Uani ? ? O17 0.7971(5) 0.5297(5) -0.1416(4) 0.107(5) Uani ? ? H1 0.73062 0.63119 0.24166 0.047 Uiso calc C1 H2 0.76399 0.55191 0.50601 0.056 Uiso calc C2 H4a 0.89161 0.27577 0.33574 0.070 Uiso calc C4 H4b 1.10101 0.30965 0.37662 0.070 Uiso calc C4 H5a 0.92068 0.35387 0.08392 0.078 Uiso calc C5 H5b 1.01473 0.47538 0.18855 0.078 Uiso calc C5 H6 0.65576 0.39986 0.10820 0.055 Uiso calc C6 H8a 0.44617 0.48254 -0.18843 0.087 Uiso calc C8 H8b 0.48291 0.61936 -0.23879 0.087 Uiso calc C8 H9a 0.26017 0.62787 -0.12472 0.081 Uiso calc C9 H9b 0.43921 0.69013 0.01528 0.081 Uiso calc C9 H10a 0.37462 0.44350 0.05925 0.071 Uiso calc C10 H10b 0.25656 0.54349 0.11479 0.071 Uiso calc C10 H12a 1.01616 0.42089 0.75473 0.084 Uiso calc C12 H12b 1.16174 0.32481 0.69188 0.084 Uiso calc C12 H12c 0.95565 0.30788 0.68116 0.084 Uiso calc C12 H13a 0.93119 0.65526 0.05702 0.107 Uiso calc C13 H13b 0.77322 0.71732 -0.10714 0.107 Uiso calc C13 H14a 0.36283 0.64239 0.37946 0.089 Uiso calc C14 H14b 0.57671 0.65350 0.49509 0.089 Uiso calc C14 H14c 0.49239 0.72220 0.30782 0.089 Uiso calc C14 H15a 0.38523 0.41858 0.38825 0.075 Uiso calc C15 H15b 0.53205 0.35093 0.32555 0.075 Uiso calc C15 H15c 0.59875 0.42874 0.50577 0.075 Uiso calc C15 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 4 1 -4 1 1 -1 1 4 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 C1 C6 114.1(3) yes C2 C1 C11 109.3(2) yes C6 C1 C11 113.7(2) yes C1 C2 C3 123.4(3) yes C1 C2 O16 118.4(3) yes C3 C2 O16 59.9(3) yes C2 C3 C4 118.3(4) yes C2 C3 C12 120.4(4) yes C2 C3 O16 59.7(3) yes C4 C3 C12 116.3(4) yes C4 C3 O16 113.3(4) yes C12 C3 O16 116.0(4) yes C3 C4 C5 111.9(4) yes C4 C5 C6 112.1(4) yes C1 C6 C5 115.0(3) yes C1 C6 C7 108.3(3) yes C5 C6 C7 111.9(3) yes C6 C7 C8 116.1(4) yes C6 C7 C13 119.8(4) yes C6 C7 O17 116.7(4) yes C8 C7 C13 119.5(4) yes C8 C7 O17 112.3(4) yes C13 C7 O17 59.3(3) yes C7 C8 C9 114.7(4) yes C8 C9 C10 113.9(4) yes C9 C10 C11 117.9(4) yes C1 C11 C10 112.5(3) yes C1 C11 C14 109.1(3) yes C1 C11 C15 110.3(3) yes C10 C11 C14 108.3(4) yes C10 C11 C15 107.3(3) yes C14 C11 C15 109.2(4) yes C7 C13 O17 59.9(3) yes C2 O16 C3 60.4(3) yes C7 O17 C13 60.7(3) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.508(4) yes C1 C6 1.552(4) yes C1 C11 1.568(5) yes C2 C3 1.466(6) yes C2 O16 1.454(4) yes C3 C4 1.490(6) yes C3 C12 1.498(6) yes C3 O16 1.457(7) yes C4 C5 1.513(6) yes C5 C6 1.531(6) yes C6 C7 1.537(6) yes C7 C8 1.506(7) yes C7 C13 1.456(8) yes C7 O17 1.444(6) yes C8 C9 1.521(7) yes C9 C10 1.529(7) yes C10 C11 1.539(5) yes C11 C14 1.532(7) yes C11 C15 1.531(7) yes C13 O17 1.435(8) 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 C1 C2 C3 C4 4.3(3) yes C2 C3 C4 C5 30.2(4) yes C3 C4 C5 C6 -57.2(4) yes C4 C5 C6 C1 50.6(4) yes C5 C6 C1 C2 -16.3(3) yes C6 C1 C2 C3 -11.3(3) yes C11 C1 C6 C7 91.5(3) yes C1 C6 C7 C8 -79.7(4) yes C6 C7 C8 C9 56.0(4) yes C7 C8 C9 C10 -65.9(5) yes C8 C9 C10 C11 87.8(5) yes C9 C10 C11 C1 -44.0(4) yes C10 C11 C1 C6 -37.1(3) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 101924093