#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/90/2009039.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_2009039 loop_ _publ_author_name 'Umehara, Misao' 'Hosomi, Hiroyuki' 'Ohba, Shigeru' _publ_section_title ; 4-Methylbicyclo[6.3.0]undecane-2,6-dione, (I), 7-bromo-4-methylbicyclo[6.3.0]undecane-2,6-dione, (II), 7-acetonyl-4-methylbicyclo[6.3.0]undecane-2,6-dione, (III), and 8-methyltricyclo[9.3.0.0^2,6^]tetradec-5-ene-4,10-dione, (IV) ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1721 _journal_page_last 1725 _journal_paper_doi 10.1107/S0108270199007088 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C12 H17 Br1 O2' _chemical_formula_sum 'C12 H17 Br O2' _chemical_formula_weight 273.17 _chemical_name_systematic ; 7-Bromo-4-methylbicyclo[6.3.0]undecane-2,6-dione ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_type_scat_source 'International Tables Vol.IV(1974)' _cell_angle_alpha 92.84(2) _cell_angle_beta 101.39(2) _cell_angle_gamma 87.87(2) _cell_formula_units_Z 2 _cell_length_a 7.4420(10) _cell_length_b 14.747(3) _cell_length_c 5.586(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298 _cell_measurement_theta_max 15.0 _cell_measurement_theta_min 14.7 _cell_volume 600.0(3) _computing_cell_refinement ' AFC/MSC Diffractometer Control System' _computing_data_collection ; AFC/MSC Diffractometer Control System (Rigaku Corporation, 1993) ; _computing_data_reduction 'local programs' _computing_molecular_graphics CRYSTAN-GM _computing_publication_material CRYSTAN-GM _computing_structure_refinement CRYSTAN-GM _computing_structure_solution ' CRYSTAN-GM (Edwards et al., 1996)' _diffrn_measurement_device_type 'Rigaku AFC-5' _diffrn_measurement_method \q-2\q _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.015 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 2286 _diffrn_reflns_theta_max 25.0 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 3.405 _exptl_absorpt_correction_T_max 0.605 _exptl_absorpt_correction_T_min 0.175 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(Coppens et al., 1965)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Plate-like _exptl_crystal_F_000 280 _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.37 _refine_diff_density_min -0.59 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.07 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 153 _refine_ls_number_reflns 1908 _refine_ls_R_factor_gt 0.042 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.0003 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0009F^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.049 _reflns_number_gt 1542 _reflns_number_total 2107 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file oa1088.cif _cod_data_source_block II _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_atom_site_thermal_displace_type' tag value 'Uij' was replaced with 'Uani' value 15 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 600.1(3) _cod_original_sg_symbol_H-M 'P -1 ' _cod_original_formula_sum 'C12 H17 Br1 O2' _cod_database_code 2009039 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,-y,-z 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 Br1 .0808(3) .0536(2) .0847(3) -.0256(2) .0119(2) .0050(2) O2 .0750(10) .071(2) .0740(10) -.0090(10) .0400(10) .0230(10) O3 .0710(10) .081(2) .0350(10) -.0030(10) .0130(10) .0020(10) C4 .058(2) .044(2) .049(2) -.0040(10) .0190(10) -.0060(10) C5 .0460(10) .041(2) .044(2) .0050(10) .0180(10) .0040(10) C6 .075(2) .052(2) .072(2) .014(2) .018(2) .017(2) C7 .061(2) .088(3) .070(3) .017(2) .008(2) .016(2) C8 .038(2) .082(2) .063(2) -.0040(10) .0090(10) .010(2) C9 .0420(10) .059(2) .045(2) .0010(10) .0210(10) .0000(10) C10 .0400(10) .049(2) .044(2) -.0090(10) .0090(10) .0040(10) C11 .053(2) .040(2) .047(2) -.0050(10) .0140(10) -.0020(10) C12 .049(2) .043(2) .045(2) .0020(10) .0140(10) .0090(10) C13 .0380(10) .058(2) .040(2) .0010(10) .0060(10) .0100(10) C14 .0430(10) .055(2) .030(2) -.0130(10) .0060(10) -.0010(10) C15 .060(2) .053(2) .066(2) .011(2) .021(2) .007(2) 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_occupancy Br1 1.29550(5) .42710(2) .38620(7) .07370(10) Uani 1.000 O2 .8555(3) .1222(2) .5221(4) .0707(9) Uani 1.000 O3 1.2308(3) .2483(2) .7860(3) .0630(8) Uani 1.000 C4 1.1175(4) .3421(2) .4575(5) .0520(10) Uani 1.000 C5 .9790(3) .3165(2) .2324(5) .0437(9) Uani 1.000 C6 .8592(4) .3937(2) .1065(6) .0660(10) Uani 1.000 C7 .6862(4) .3479(3) -.0409(6) .0730(10) Uani 1.000 C8 .6988(4) .2495(2) .0376(6) .0610(10) Uani 1.000 C9 .8382(3) .2496(2) .2792(5) .0490(10) Uani 1.000 C10 .9074(3) .1563(2) .3561(5) .0444(9) Uani 1.000 C11 1.0413(3) .1057(2) .2252(5) .0480(10) Uani 1.000 C12 1.2409(3) .1051(2) .3638(5) .0450(10) Uani 1.000 C13 1.3238(3) .1990(2) .4177(5) .0450(10) Uani 1.000 C14 1.2279(3) .2622(2) .5729(5) .0440(10) Uani 1.000 C15 1.3581(4) .0447(2) .2212(6) .0600(10) Uani 1.000 H4 1.05250 .37080 .57430 .056(8) Uiso 1.000 H5 1.04710 .28980 .11640 .020(5) Uiso 1.000 H6A .92190 .42490 .00190 .070(9) Uiso 1.000 H6B .82680 .43630 .22760 .090(10) Uiso 1.000 H7A .68480 .35010 -.21280 .110(10) Uiso 1.000 H7B .57710 .37790 -.00570 .110(10) Uiso 1.000 H8A .74230 .20970 -.08120 .067(9) Uiso 1.000 H8B .58130 .22990 .05760 .056(8) Uiso 1.000 H9 .78190 .27260 .41130 .051(8) Uiso 1.000 H11A 1.03870 .13390 .07320 .052(8) Uiso 1.000 H11B 1.00300 .04420 .19180 .054(8) Uiso 1.000 H12 1.24170 .07940 .51860 .035(6) Uiso 1.000 H13A 1.32020 .22600 .26380 .030(6) Uiso 1.000 H13B 1.44930 .19180 .49960 .042(7) Uiso 1.000 H15A 1.48170 .04410 .31270 .070(10) Uiso 1.000 H15B 1.35380 .06880 .06360 .080(10) Uiso 1.000 H15C 1.31280 -.01590 .19970 .080(10) Uiso 1.000 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 Br1 C4 C5 111.6(2) no Br1 C4 C14 106.3(2) no C5 C4 C14 113.6(3) no C4 C5 C6 116.8(3) no C4 C5 C9 113.4(3) no C6 C5 C9 103.1(2) no C5 C6 C7 105.3(3) no C6 C7 C8 105.9(3) no C7 C8 C9 105.2(3) no C5 C9 C8 101.9(3) no C5 C9 C10 117.5(2) no C8 C9 C10 113.7(3) no O2 C10 C9 120.1(3) no O2 C10 C11 120.3(3) no C9 C10 C11 119.6(3) no C10 C11 C12 114.9(3) no C11 C12 C13 114.7(3) no C11 C12 C15 109.2(3) no C13 C12 C15 110.0(3) no C12 C13 C14 114.8(3) no O3 C14 C4 119.4(3) no O3 C14 C13 121.5(3) no C4 C14 C13 119.0(3) no Br1 C4 H4 108.9 no C5 C4 H4 107.8 no C14 C4 H4 108.6 no C4 C5 H5 106.4 no C6 C5 H5 107.1 no C9 C5 H5 109.9 no C5 C6 H6A 111.3 no C5 C6 H6B 109.6 no C7 C6 H6A 111.3 no C7 C6 H6B 110.3 no H6A C6 H6B 109.0 no C6 C7 H7A 109.9 no C6 C7 H7B 110.8 no C8 C7 H7A 110.7 no C8 C7 H7B 110.5 no H7A C7 H7B 109.0 no C7 C8 H8A 110.8 no C7 C8 H8B 110.7 no C9 C8 H8A 109.6 no C9 C8 H8B 111.5 no H8A C8 H8B 109.0 no C5 C9 H9 110.1 no C8 C9 H9 110.4 no C10 C9 H9 103.4 no C10 C11 H11A 108.4 no C10 C11 H11B 108.6 no C12 C11 H11A 107.0 no C12 C11 H11B 108.9 no H11A C11 H11B 109.0 no C11 C12 H12 106.6 no C13 C12 H12 107.0 no C15 C12 H12 109.2 no C12 C13 H13A 107.6 no C12 C13 H13B 108.7 no C14 C13 H13A 108.7 no C14 C13 H13B 108.1 no H13A C13 H13B 108.9 no C12 C15 H15A 107.9 no C12 C15 H15B 109.6 no C12 C15 H15C 110.2 no H15A C15 H15B 110.1 no H15A C15 H15C 110.0 no H15B C15 H15C 109.0 no 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 Br1 C4 . . 1.966(3) yes O2 C10 . . 1.210(4) yes O3 C14 . . 1.214(4) yes C4 C5 . . 1.502(4) yes C4 C14 . . 1.508(5) yes C5 C6 . . 1.530(5) yes C5 C9 . . 1.533(4) yes C6 C7 . . 1.544(5) yes C7 C8 . . 1.531(6) yes C8 C9 . . 1.531(5) yes C9 C10 . . 1.504(5) yes C10 C11 . . 1.504(4) yes C11 C12 . . 1.533(4) yes C12 C13 . . 1.529(4) yes C12 C15 . . 1.528(5) yes C13 C14 . . 1.498(4) yes C4 H4 . . .960 no C5 H5 . . .960 no C6 H6A . . .960 no C6 H6B . . .960 no C7 H7A . . .960 no C7 H7B . . .960 no C8 H8A . . .960 no C8 H8B . . .960 no C9 H9 . . .960 no C11 H11A . . .960 no C11 H11B . . .959 no C12 H12 . . .960 no C13 H13A . . .960 no C13 H13B . . .960 no C15 H15A . . .960 no C15 H15B . . .960 no C15 H15C . . .960 no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 100992226