#------------------------------------------------------------------------------ #$Date: 2014-03-15 13:45:36 +0200 (Sat, 15 Mar 2014) $ #$Revision: 106525 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/10/18/7101810.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7101810 loop_ _publ_author_name 'Cergol, Katie M' 'Jensen, Paul' 'Turner, Peter' 'Coster, Mark J' _publ_section_title ; Reversibility in the boron-mediated ketone-ketone aldol reaction. ; _journal_issue 13 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 1363 _journal_page_last 1365 _journal_year 2007 _chemical_formula_moiety 'C20 H36 O2' _chemical_formula_sum 'C20 H36 O2' _chemical_formula_weight 308.49 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 104.982(1) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.179(1) _cell_length_b 12.282(1) _cell_length_c 12.063(1) _cell_measurement_reflns_used 8700 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 28.2726 _cell_measurement_theta_min 2.3041 _cell_volume 1886.2(3) _computing_cell_refinement 'SAINT Ver. 6.45 (Bruker-AXS, 2003)' _computing_data_collection 'SMART Ver. 5.054 (Bruker-AXS, 1998)' _computing_data_reduction 'SAINT Ver. 6.45' _computing_molecular_graphics 'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)' _computing_publication_material 'modiCIFer-12162005 (Guzei, 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 150(2) _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.954 _diffrn_measurement_device_type 'Bruker CCD-1000 area detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 18394 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 28.32 _diffrn_reflns_theta_min 2.30 _diffrn_standards_decay_% 0.35 _diffrn_standards_number 207 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_T_max 0.972 _exptl_absorpt_correction_T_min 0.928 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS (Bruker-AXS, 2004) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.086 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 688 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.43 _refine_diff_density_max 0.367 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.037 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 4483 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0411 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0686P)^2^+0.3458P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1114 _refine_ls_wR_factor_ref 0.1230 _reflns_number_gt 3692 _reflns_number_total 4483 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file b617094c.txt _[local]_cod_data_source_block mc06pj4 _[local]_cod_cif_authors_sg_H-M 'P 1 21/c 1 ' _[local]_cod_cif_authors_sg_Hall '-P 2ybc ' _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 ; _cod_database_code 7101810 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags O1 O 0.37039(6) 0.02713(6) 0.26558(6) 0.03198(19) Uani 1 1 d . O2 O 0.37656(8) 0.24779(7) 0.30787(7) 0.0442(2) Uani 1 1 d . C1 C 0.04939(10) -0.28392(10) 0.08643(11) 0.0398(3) Uani 1 1 d . H1A H 0.0077 -0.3427 0.1075 0.060 Uiso 1 1 calc R H1B H 0.1171 -0.3129 0.0805 0.060 Uiso 1 1 calc R H1C H 0.0115 -0.2530 0.0124 0.060 Uiso 1 1 calc R C2 C -0.03956(10) -0.15887(12) 0.19180(14) 0.0504(3) Uani 1 1 d . H2A H -0.0801 -0.2230 0.2029 0.076 Uiso 1 1 calc R H2B H -0.0774 -0.1199 0.1225 0.076 Uiso 1 1 calc R H2C H -0.0300 -0.1106 0.2584 0.076 Uiso 1 1 calc R C3 C 0.13157(11) -0.24347(10) 0.29216(11) 0.0423(3) Uani 1 1 d . H3A H 0.1410 -0.1884 0.3527 0.064 Uiso 1 1 calc R H3B H 0.2004 -0.2669 0.2843 0.064 Uiso 1 1 calc R H3C H 0.0939 -0.3062 0.3123 0.064 Uiso 1 1 calc R C4 C 0.06809(8) -0.19495(9) 0.17857(10) 0.0320(2) Uani 1 1 d . C5 C 0.12502(8) -0.09592(8) 0.14042(9) 0.0274(2) Uani 1 1 d . H5 H 0.0782 -0.0688 0.0666 0.033 Uiso 1 1 calc R C6 C 0.14133(9) -0.00089(9) 0.22554(10) 0.0330(2) Uani 1 1 d . H6A H 0.0725 0.0216 0.2367 0.040 Uiso 1 1 calc R H6B H 0.1858 -0.0254 0.3006 0.040 Uiso 1 1 calc R C7 C 0.19316(8) 0.09674(8) 0.18417(10) 0.0303(2) Uani 1 1 d . H7A H 0.2033 0.1552 0.2425 0.036 Uiso 1 1 calc R H7B H 0.1459 0.1250 0.1123 0.036 Uiso 1 1 calc R C8 C 0.29970(7) 0.06797(8) 0.16236(8) 0.0240(2) Uani 1 1 d . C9 C 0.28349(8) -0.02594(8) 0.07648(9) 0.0265(2) Uani 1 1 d . H9A H 0.3524 -0.0484 0.0655 0.032 Uiso 1 1 calc R H9B H 0.2394 -0.0006 0.0015 0.032 Uiso 1 1 calc R C10 C 0.23074(8) -0.12443(8) 0.11646(9) 0.0276(2) Uani 1 1 d . H10A H 0.2783 -0.1544 0.1872 0.033 Uiso 1 1 calc R H10B H 0.2195 -0.1817 0.0567 0.033 Uiso 1 1 calc R C11 C 0.34790(7) 0.16896(8) 0.11942(8) 0.0236(2) Uani 1 1 d . H11 H 0.2944 0.1974 0.0510 0.028 Uiso 1 1 calc R C12 C 0.44947(8) 0.14568(8) 0.08074(9) 0.0297(2) Uani 1 1 d . H12A H 0.4912 0.0895 0.1315 0.036 Uiso 1 1 calc R H12B H 0.4299 0.1163 0.0016 0.036 Uiso 1 1 calc R C13 C 0.51733(9) 0.24792(9) 0.08406(11) 0.0355(3) Uani 1 1 d . H13A H 0.5689 0.2529 0.1598 0.043 Uiso 1 1 calc R H13B H 0.5567 0.2419 0.0247 0.043 Uiso 1 1 calc R C14 C 0.45044(9) 0.35092(9) 0.06316(9) 0.0308(2) Uani 1 1 d . H14A H 0.3941 0.3433 -0.0088 0.037 Uiso 1 1 calc R H14B H 0.4945 0.4141 0.0549 0.037 Uiso 1 1 calc R C15 C 0.40176(8) 0.36997(8) 0.16410(8) 0.0252(2) Uani 1 1 d . H15 H 0.4583 0.4018 0.2275 0.030 Uiso 1 1 calc R C16 C 0.37342(8) 0.26107(8) 0.20701(8) 0.0266(2) Uani 1 1 d . C17 C 0.30801(8) 0.45200(8) 0.14052(9) 0.0274(2) Uani 1 1 d . C18 C 0.20919(8) 0.40669(9) 0.05613(10) 0.0358(3) Uani 1 1 d . H18A H 0.1834 0.3436 0.0905 0.054 Uiso 1 1 calc R H18B H 0.2263 0.3845 -0.0149 0.054 Uiso 1 1 calc R H18C H 0.1548 0.4631 0.0389 0.054 Uiso 1 1 calc R C19 C 0.28080(9) 0.47964(10) 0.25331(10) 0.0366(3) Uani 1 1 d . H19A H 0.2212 0.5301 0.2380 0.055 Uiso 1 1 calc R H19B H 0.3416 0.5138 0.3062 0.055 Uiso 1 1 calc R H19C H 0.2622 0.4128 0.2879 0.055 Uiso 1 1 calc R C20 C 0.34162(9) 0.55678(9) 0.09036(11) 0.0357(3) Uani 1 1 d . H20A H 0.2878 0.6129 0.0857 0.054 Uiso 1 1 calc R H20B H 0.3500 0.5420 0.0134 0.054 Uiso 1 1 calc R H20C H 0.4085 0.5823 0.1400 0.054 Uiso 1 1 calc R H1 H 0.3801(11) 0.0797(12) 0.3118(13) 0.043 Uiso 1 1 d . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0381(4) 0.0277(4) 0.0263(4) 0.0047(3) 0.0016(3) 0.0019(3) O2 0.0769(7) 0.0330(4) 0.0219(4) 0.0006(3) 0.0112(4) -0.0077(4) C1 0.0359(6) 0.0375(6) 0.0448(7) -0.0011(5) 0.0083(5) -0.0106(5) C2 0.0371(6) 0.0468(7) 0.0759(9) 0.0059(7) 0.0301(7) -0.0028(5) C3 0.0558(7) 0.0344(6) 0.0373(6) 0.0077(5) 0.0130(5) -0.0060(5) C4 0.0290(5) 0.0302(5) 0.0385(6) 0.0039(4) 0.0119(4) -0.0023(4) C5 0.0249(5) 0.0269(5) 0.0310(5) 0.0044(4) 0.0086(4) 0.0010(4) C6 0.0370(6) 0.0276(5) 0.0411(6) 0.0008(4) 0.0222(5) 0.0018(4) C7 0.0324(5) 0.0240(5) 0.0385(6) 0.0007(4) 0.0166(4) 0.0035(4) C8 0.0257(5) 0.0229(4) 0.0232(4) 0.0025(3) 0.0060(4) 0.0025(4) C9 0.0270(5) 0.0260(5) 0.0287(5) -0.0013(4) 0.0110(4) 0.0000(4) C10 0.0282(5) 0.0236(5) 0.0323(5) -0.0013(4) 0.0105(4) 0.0005(4) C11 0.0244(5) 0.0245(5) 0.0215(4) 0.0014(3) 0.0053(3) 0.0006(3) C12 0.0275(5) 0.0289(5) 0.0339(5) -0.0007(4) 0.0102(4) 0.0012(4) C13 0.0286(5) 0.0355(6) 0.0449(6) -0.0037(5) 0.0144(5) -0.0029(4) C14 0.0331(5) 0.0293(5) 0.0333(5) -0.0009(4) 0.0146(4) -0.0057(4) C15 0.0256(5) 0.0253(5) 0.0238(4) -0.0012(4) 0.0047(4) -0.0038(4) C16 0.0295(5) 0.0264(5) 0.0228(5) 0.0007(4) 0.0048(4) 0.0000(4) C17 0.0260(5) 0.0248(5) 0.0318(5) 0.0008(4) 0.0080(4) -0.0030(4) C18 0.0284(5) 0.0329(6) 0.0414(6) 0.0038(5) 0.0002(4) -0.0022(4) C19 0.0362(6) 0.0358(6) 0.0418(6) -0.0047(5) 0.0174(5) -0.0036(5) C20 0.0352(6) 0.0274(5) 0.0461(6) 0.0058(5) 0.0132(5) -0.0024(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C8 O1 H1 105.1(10) C4 C1 H1A 109.5 C4 C1 H1B 109.5 H1A C1 H1B 109.5 C4 C1 H1C 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 C4 C2 H2A 109.5 C4 C2 H2B 109.5 H2A C2 H2B 109.5 C4 C2 H2C 109.5 H2A C2 H2C 109.5 H2B C2 H2C 109.5 C4 C3 H3A 109.5 C4 C3 H3B 109.5 H3A C3 H3B 109.5 C4 C3 H3C 109.5 H3A C3 H3C 109.5 H3B C3 H3C 109.5 C3 C4 C1 108.67(10) C3 C4 C2 109.01(11) C1 C4 C2 107.57(10) C3 C4 C5 112.01(9) C1 C4 C5 109.97(9) C2 C4 C5 109.51(9) C6 C5 C10 108.84(8) C6 C5 C4 113.02(9) C10 C5 C4 114.02(8) C6 C5 H5 106.8 C10 C5 H5 106.8 C4 C5 H5 106.8 C7 C6 C5 112.11(9) C7 C6 H6A 109.2 C5 C6 H6A 109.2 C7 C6 H6B 109.2 C5 C6 H6B 109.2 H6A C6 H6B 107.9 C6 C7 C8 112.44(8) C6 C7 H7A 109.1 C8 C7 H7A 109.1 C6 C7 H7B 109.1 C8 C7 H7B 109.1 H7A C7 H7B 107.8 O1 C8 C9 105.63(8) O1 C8 C7 110.37(8) C9 C8 C7 108.43(8) O1 C8 C11 109.88(8) C9 C8 C11 112.14(8) C7 C8 C11 110.28(8) C8 C9 C10 112.18(8) C8 C9 H9A 109.2 C10 C9 H9A 109.2 C8 C9 H9B 109.2 C10 C9 H9B 109.2 H9A C9 H9B 107.9 C9 C10 C5 112.75(8) C9 C10 H10A 109.0 C5 C10 H10A 109.0 C9 C10 H10B 109.0 C5 C10 H10B 109.0 H10A C10 H10B 107.8 C16 C11 C8 113.58(8) C16 C11 C12 106.97(8) C8 C11 C12 114.47(8) C16 C11 H11 107.1 C8 C11 H11 107.1 C12 C11 H11 107.1 C13 C12 C11 112.50(8) C13 C12 H12A 109.1 C11 C12 H12A 109.1 C13 C12 H12B 109.1 C11 C12 H12B 109.1 H12A C12 H12B 107.8 C14 C13 C12 111.46(9) C14 C13 H13A 109.3 C12 C13 H13A 109.3 C14 C13 H13B 109.3 C12 C13 H13B 109.3 H13A C13 H13B 108.0 C13 C14 C15 109.74(9) C13 C14 H14A 109.7 C15 C14 H14A 109.7 C13 C14 H14B 109.7 C15 C14 H14B 109.7 H14A C14 H14B 108.2 C16 C15 C14 109.10(8) C16 C15 C17 112.22(8) C14 C15 C17 115.29(8) C16 C15 H15 106.6 C14 C15 H15 106.6 C17 C15 H15 106.6 O2 C16 C15 120.79(9) O2 C16 C11 122.50(9) C15 C16 C11 116.60(8) C19 C17 C18 108.42(9) C19 C17 C20 108.78(9) C18 C17 C20 108.92(9) C19 C17 C15 109.69(8) C18 C17 C15 112.48(8) C20 C17 C15 108.49(8) C17 C18 H18A 109.5 C17 C18 H18B 109.5 H18A C18 H18B 109.5 C17 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 C17 C19 H19A 109.5 C17 C19 H19B 109.5 H19A C19 H19B 109.5 C17 C19 H19C 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 C17 C20 H20A 109.5 C17 C20 H20B 109.5 H20A C20 H20B 109.5 C17 C20 H20C 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C8 1.4388(12) O1 H1 0.842(15) O2 C16 1.2177(13) C1 C4 1.5325(17) C1 H1A 0.9800 C1 H1B 0.9800 C1 H1C 0.9800 C2 C4 1.5336(16) C2 H2A 0.9800 C2 H2B 0.9800 C2 H2C 0.9800 C3 C4 1.5297(17) C3 H3A 0.9800 C3 H3B 0.9800 C3 H3C 0.9800 C4 C5 1.5595(14) C5 C6 1.5325(15) C5 C10 1.5348(14) C5 H5 1.0000 C6 C7 1.5264(14) C6 H6A 0.9900 C6 H6B 0.9900 C7 C8 1.5352(14) C7 H7A 0.9900 C7 H7B 0.9900 C8 C9 1.5279(13) C8 C11 1.5428(13) C9 C10 1.5338(14) C9 H9A 0.9900 C9 H9B 0.9900 C10 H10A 0.9900 C10 H10B 0.9900 C11 C16 1.5250(13) C11 C12 1.5537(13) C11 H11 1.0000 C12 C13 1.5362(15) C12 H12A 0.9900 C12 H12B 0.9900 C13 C14 1.5252(15) C13 H13A 0.9900 C13 H13B 0.9900 C14 C15 1.5339(14) C14 H14A 0.9900 C14 H14B 0.9900 C15 C16 1.5153(13) C15 C17 1.5624(14) C15 H15 1.0000 C17 C19 1.5320(15) C17 C18 1.5350(14) C17 C20 1.5353(14) C18 H18A 0.9800 C18 H18B 0.9800 C18 H18C 0.9800 C19 H19A 0.9800 C19 H19B 0.9800 C19 H19C 0.9800 C20 H20A 0.9800 C20 H20B 0.9800 C20 H20C 0.9800 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O1 H1 O2 0.842(15) 2.065(15) 2.7550(12) 138.9(13) 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 C3 C4 C5 C6 -62.08(12) C1 C4 C5 C6 176.98(9) C2 C4 C5 C6 58.98(13) C3 C4 C5 C10 62.91(12) C1 C4 C5 C10 -58.03(12) C2 C4 C5 C10 -176.02(10) C10 C5 C6 C7 54.54(11) C4 C5 C6 C7 -177.71(8) C5 C6 C7 C8 -57.69(12) C6 C7 C8 O1 -59.07(11) C6 C7 C8 C9 56.18(11) C6 C7 C8 C11 179.32(8) O1 C8 C9 C10 63.06(10) C7 C8 C9 C10 -55.25(10) C11 C8 C9 C10 -177.27(8) C8 C9 C10 C5 56.52(11) C6 C5 C10 C9 -54.14(11) C4 C5 C10 C9 178.67(8) O1 C8 C11 C16 -58.17(10) C9 C8 C11 C16 -175.33(8) C7 C8 C11 C16 63.73(11) O1 C8 C11 C12 65.09(10) C9 C8 C11 C12 -52.06(11) C7 C8 C11 C12 -173.01(8) C16 C11 C12 C13 -30.83(11) C8 C11 C12 C13 -157.59(9) C11 C12 C13 C14 -29.40(13) C12 C13 C14 C15 67.27(12) C13 C14 C15 C16 -36.38(11) C13 C14 C15 C17 -163.70(8) C14 C15 C16 O2 148.50(10) C17 C15 C16 O2 -82.46(12) C14 C15 C16 C11 -27.85(12) C17 C15 C16 C11 101.18(10) C8 C11 C16 O2 14.74(14) C12 C11 C16 O2 -112.54(11) C8 C11 C16 C15 -168.98(8) C12 C11 C16 C15 63.74(11) C16 C15 C17 C19 64.87(10) C14 C15 C17 C19 -169.40(8) C16 C15 C17 C18 -55.88(11) C14 C15 C17 C18 69.84(11) C16 C15 C17 C20 -176.44(8) C14 C15 C17 C20 -50.71(11) _journal_paper_doi 10.1039/b617094c