#------------------------------------------------------------------------------ #$Date: 2016-02-19 14:29:56 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176759 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/90/2009041.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_2009041 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 'C15 H22 O3' _chemical_formula_sum 'C15 H22 O3' _chemical_formula_weight 250.34 _chemical_name_common ; 7-Acetonyl-4-methylbicyclo[6.3.0]undecane-2,6-dione ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_type_scat_source 'International Tables Vol.IV(1974)' _cell_angle_alpha 90.00000 _cell_angle_beta 114.00(2) _cell_angle_gamma 90.00000 _cell_formula_units_Z 4 _cell_length_a 7.874(2) _cell_length_b 21.134(3) _cell_length_c 9.220(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 297 _cell_measurement_theta_max 14.9 _cell_measurement_theta_min 13.8 _cell_volume 1401.6(6) _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 0.017 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 2961 _diffrn_reflns_theta_max 26.0 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.20 _refine_diff_density_min -0.23 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.07 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 185 _refine_ls_number_reflns 2343 _refine_ls_R_factor_gt 0.053 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.0007 _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 0.063 _reflns_number_gt 1707 _reflns_number_total 2760 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file oa1088.cif _cod_data_source_block III _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 18 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 'Monoclinic' changed to 'monoclinic' 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 1401.7(7) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2009041 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,-y,-z -x+1/2,+y+1/2,-z+1/2 +x+1/2,-y+1/2,+z+1/2 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 O1 .0395(6) .0780(8) .0630(7) .0001(6) .0095(6) -.0112(6) O2 .0658(8) .0580(8) .1020(11) .0176(6) .0209(8) .0121(7) O3 .0802(9) .0525(7) .0617(7) -.0023(6) .0342(6) .0024(6) C4 .0441(8) .0317(7) .0542(9) -.0006(6) .0184(7) -.0032(7) C5 .0397(7) .0369(8) .0387(8) .0023(6) .0134(6) -.0016(6) C6 .0406(8) .0422(8) .0461(9) .0017(6) .0130(7) .0036(7) C7 .0580(10) .0580(10) .0640(10) .0000(10) .0340(10) .0030(10) C8 .0770(10) .0690(10) .117(2) -.0140(10) .0570(10) -.0020(10) C9 .0810(10) .0500(10) .110(2) -.0110(10) .0520(10) .0050(10) C10 .0469(9) .0406(9) .0602(10) -.0032(7) .0188(8) -.0001(7) C11 .0510(10) .0300(10) .0830(10) -.0030(10) .0230(10) -.0080(10) C12 .0481(9) .0495(10) .0875(13) .0004(8) .0276(9) -.0224(9) C13 .0436(9) .0657(11) .0575(10) .0020(8) .0238(8) -.0176(8) C14 .0525(9) .0526(10) .0595(10) -.0014(7) .0283(8) -.0086(8) C15 .0730(10) .114(2) .0670(10) .0050(10) .0300(10) -.0300(10) C16 .0479(9) .0421(9) .0516(9) .0028(7) .0212(8) -.0025(7) C17 .0397(8) .0389(8) .0549(9) .0043(6) .0163(7) -.0017(7) C18 .0800(10) .0470(10) .0750(10) -.0030(10) .0320(10) -.0140(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_occupancy O1 .47870(10) .05060(6) .19250(10) .0706(5) Uani 1.000 O2 .5904(2) .21630(6) .1994(2) .0824(6) Uani 1.000 O3 .7384(2) -.07340(5) .38540(10) .0734(5) Uani 1.000 C4 .6249(2) .05560(6) .3083(2) .0509(6) Uani 1.000 C5 .8076(2) .04600(6) .2912(2) .0441(5) Uani 1.000 C6 .8544(2) .10400(7) .2144(2) .0475(6) Uani 1.000 C7 1.0344(2) .09800(8) .1882(2) .0671(7) Uani 1.000 C8 1.0965(3) .16570(10) .1773(3) .1010(10) Uani 1.000 C9 .9750(3) .20920(9) .2256(3) .0910(10) Uani 1.000 C10 .8869(2) .16630(7) .3096(2) .0563(6) Uani 1.000 C11 .7117(2) .19250(7) .3164(2) .0664(7) Uani 1.000 C12 .6929(2) .18880(8) .4709(2) .0779(8) Uani 1.000 C13 .7470(2) .12590(8) .5605(2) .0680(7) Uani 1.000 C14 .6254(2) .07080(7) .4679(2) .0651(7) Uani 1.000 C15 .7372(3) .13150(10) .7224(2) .1030(10) Uani 1.000 C16 .7920(2) -.01320(7) .1910(2) .0546(6) Uani 1.000 C17 .7479(2) -.07260(6) .2570(2) .0513(6) Uani 1.000 C18 .7161(3) -.13140(8) .1579(2) .0818(9) Uani 1.000 H5 .90520 .04080 .39510 .030(3) Uiso 1.000 H6 .75270 .11000 .11300 .041(4) Uiso 1.000 H7A 1.01160 .07530 .09190 .075(5) Uiso 1.000 H7B 1.12680 .07580 .27570 .080(6) Uiso 1.000 H8A 1.08390 .17460 .07140 .160(10) Uiso 1.000 H8B 1.22420 .17120 .24930 .104(7) Uiso 1.000 H9A .87830 .22710 .13310 .095(7) Uiso 1.000 H9B 1.04570 .24290 .29300 .093(7) Uiso 1.000 H10 .97470 .15900 .41670 .037(4) Uiso 1.000 H12A .56530 .19670 .45140 .064(5) Uiso 1.000 H12B .76890 .22150 .53870 .091(6) Uiso 1.000 H13 .87200 .11660 .57440 .041(4) Uiso 1.000 H14A .66420 .03360 .53280 .071(5) Uiso 1.000 H14B .50010 .08090 .45180 .060(5) Uiso 1.000 H15A .77350 .09170 .77660 .091(7) Uiso 1.000 H15B .61200 .14130 .70680 .085(6) Uiso 1.000 H15C .81840 .16430 .78450 .108(7) Uiso 1.000 H16A .90790 -.01920 .18150 .067(5) Uiso 1.000 H16B .69580 -.00580 .08750 .059(5) Uiso 1.000 H18A .72350 -.13050 .05660 .140(10) Uiso 1.000 H18B .59350 -.14600 .13900 .160(10) Uiso 1.000 H18C .80520 -.16220 .22100 .170(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 O1 C4 C5 119.6(2) no O1 C4 C14 120.2(2) no C5 C4 C14 120.2(2) no C4 C5 C6 110.8(2) no C4 C5 C16 108.9(2) no C6 C5 C16 110.5(2) no C5 C6 C7 114.6(2) no C5 C6 C10 115.7(2) no C7 C6 C10 102.1(2) no C6 C7 C8 105.9(2) no C7 C8 C9 106.9(2) no C8 C9 C10 105.0(2) no C6 C10 C9 102.8(2) no C6 C10 C11 113.1(2) no C9 C10 C11 114.4(2) no O2 C11 C10 120.9(2) no O2 C11 C12 121.3(2) no C10 C11 C12 117.8(2) no C11 C12 C13 116.5(2) no C12 C13 C14 112.7(2) no C12 C13 C15 110.2(2) no C14 C13 C15 109.6(2) no C4 C14 C13 117.4(2) no C5 C16 C17 114.5(2) no O3 C17 C16 121.6(2) no O3 C17 C18 121.3(2) no C16 C17 C18 117.1(2) no C4 C5 H5 108.6 no C6 C5 H5 107.9 no C16 C5 H5 110.1 no C5 C6 H6 107.0 no C7 C6 H6 108.4 no C10 C6 H6 108.7 no C6 C7 H7A 110.4 no C6 C7 H7B 109.9 no C8 C7 H7A 110.6 no C8 C7 H7B 111.0 no H7A C7 H7B 109.0 no C7 C8 H8A 110.3 no C7 C8 H8B 109.9 no C9 C8 H8A 111.3 no C9 C8 H8B 109.4 no H8A C8 H8B 109.0 no C8 C9 H9A 110.2 no C8 C9 H9B 111.7 no C10 C9 H9A 108.9 no C10 C9 H9B 112.0 no H9A C9 H9B 108.9 no C6 C10 H10 109.3 no C9 C10 H10 109.3 no C11 C10 H10 107.7 no C11 C12 H12A 108.3 no C11 C12 H12B 107.8 no C13 C12 H12A 107.0 no C13 C12 H12B 108.1 no H12A C12 H12B 108.9 no C12 C13 H13 107.2 no C14 C13 H13 107.1 no C15 C13 H13 110.0 no C4 C14 H14A 108.0 no C4 C14 H14B 107.6 no C13 C14 H14A 107.9 no C13 C14 H14B 106.7 no H14A C14 H14B 109.0 no C13 C15 H15A 108.5 no C13 C15 H15B 109.1 no C13 C15 H15C 110.6 no H15A C15 H15B 109.7 no H15A C15 H15C 109.7 no H15B C15 H15C 109.2 no C5 C16 H16A 108.5 no C5 C16 H16B 107.7 no C17 C16 H16A 108.2 no C17 C16 H16B 108.7 no H16A C16 H16B 109.0 no C17 C18 H18A 121.0 no C17 C18 H18B 106.4 no C17 C18 H18C 107.0 no H18A C18 H18B 106.5 no H18A C18 H18C 106.5 no H18B C18 H18C 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 O1 C4 . . 1.215(2) yes O2 C11 . . 1.221(3) yes O3 C17 . . 1.216(2) yes C4 C5 . . 1.523(3) yes C4 C14 . . 1.505(3) yes C5 C6 . . 1.534(3) yes C5 C16 . . 1.530(3) yes C6 C7 . . 1.537(3) yes C6 C10 . . 1.545(3) yes C7 C8 . . 1.528(3) yes C8 C9 . . 1.518(4) yes C9 C10 . . 1.530(3) yes C10 C11 . . 1.511(3) yes C11 C12 . . 1.493(3) yes C12 C13 . . 1.531(3) yes C13 C14 . . 1.529(3) yes C13 C15 . . 1.530(3) yes C16 C17 . . 1.496(3) yes C17 C18 . . 1.502(3) yes C5 H5 . . .960 no C6 H6 . . .960 no C7 H7A . . .960 no C7 H7B . . .961 no C8 H8A . . .959 no C8 H8B . . .960 no C9 H9A . . .960 no C9 H9B . . .960 no C10 H10 . . .960 no C12 H12A . . .961 no C12 H12B . . .960 no C13 H13 . . .960 no C14 H14A . . .960 no C14 H14B . . .960 no C15 H15A . . .961 no C15 H15B . . .959 no C15 H15C . . .959 no C16 H16A . . .960 no C16 H16B . . .960 no C18 H18A . . .959 no C18 H18B . . .959 no C18 H18C . . .960 no