#------------------------------------------------------------------------------ #$Date: 2015-12-03 13:26:14 +0200 (Thu, 03 Dec 2015) $ #$Revision: 170678 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/80/7118073.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_7118073 loop_ _publ_author_name 'Shivakrishna Kallepu' 'Krishna Kumar Gollapelli' 'Jagadeesh Babu Nanubolu' 'Rambabu Chegondi' _publ_section_title ; Synthesis of highly strained bicyclic[3.n.1]alkenes by a metal-catalyzed Conia-ene reaction ; _journal_name_full Chem.Commun. _journal_page_first 16840 _journal_paper_doi 10.1039/C5cc05926G _journal_volume 51 _journal_year 2015 _chemical_formula_moiety 'C15 H14 O2' _chemical_formula_sum 'C15 H14 O2' _chemical_formula_weight 226.26 _chemical_name_systematic 5-methyl-2-phenylbicyclo[3.2.1]oct-2-ene-6,8-dione _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2015-07-10 deposited with the CCDC. 2015-09-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.0820(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.4961(8) _cell_length_b 6.0394(4) _cell_length_c 16.0699(10) _cell_measurement_reflns_used 7252 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.22 _cell_measurement_theta_min 2.61 _cell_volume 1176.33(13) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_unetI/netI 0.0162 _diffrn_reflns_laue_measured_fraction_full 0.998 _diffrn_reflns_laue_measured_fraction_max 0.973 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 13090 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.973 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.284 _diffrn_reflns_theta_min 1.861 _diffrn_source 'sealed tube' _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.278 _exptl_crystal_description plate _exptl_crystal_F_000 480 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Dichloromethane/Hexane' _exptl_crystal_size_max 0.490 _exptl_crystal_size_mid 0.380 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.284 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.046 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 2830 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0443 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0749P)^2^+0.2197P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1218 _refine_ls_wR_factor_ref 0.1270 _reflns_Friedel_coverage 0.000 _reflns_friedel_fraction_full . _reflns_friedel_fraction_max . _reflns_number_gt 2535 _reflns_number_total 2830 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c5cc05926g2.cif _cod_data_source_block BA38M _cod_database_code 7118073 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.960 _shelx_estimated_absorpt_t_max 0.992 _exptl_absorpt_special_details 'Sheldrick,G.M.,(2003),University of gottingen,Germany' _shelx_res_file ; BA38M.res created by SHELXL-2014/7 TITL BA38M in P2(1)/n CELL 0.71073 12.4961 6.0394 16.0699 90.000 104.082 90.000 ZERR 4.00 0.0008 0.0004 0.0010 0.000 0.001 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H O UNIT 60 56 8 L.S. 20 ACTA BOND $H FMAP 2 PLAN 5 SIZE 0.49 0.38 0.10 TEMP 20 WGHT 0.074900 0.219700 FVAR 0.80612 MOLE 1 C1 1 1.058576 0.797390 0.154725 11.00000 0.03155 0.03183 = 0.03734 -0.00198 0.00724 0.00142 C2 1 1.054330 0.708387 0.242491 11.00000 0.03838 0.03031 = 0.04390 0.00292 0.01417 0.00223 AFIX 23 H2A 2 1.115467 0.608671 0.264676 11.00000 -1.20000 H2B 2 0.985640 0.630551 0.239678 11.00000 -1.20000 AFIX 0 C3 1 1.062745 0.917178 0.298629 11.00000 0.03166 0.03707 = 0.03083 0.00180 0.00753 0.00143 AFIX 13 H3 2 1.098367 0.888798 0.359066 11.00000 -1.20000 AFIX 0 C4 1 1.128239 1.074647 0.256527 11.00000 0.02998 0.03298 = 0.03423 -0.00202 0.00760 0.00176 C5 1 1.081756 1.045658 0.160983 11.00000 0.03451 0.03113 = 0.03128 0.00015 0.00876 -0.00172 C6 1 1.150532 1.132124 0.102427 11.00000 0.04508 0.04817 = 0.03924 0.00494 0.01539 -0.00487 AFIX 137 H6A 2 1.171734 1.282438 0.117475 11.00000 -1.50000 H6B 2 1.108079 1.126404 0.044007 11.00000 -1.50000 H6C 2 1.215411 1.042379 0.108653 11.00000 -1.50000 AFIX 0 C7 1 0.966524 1.161380 0.143083 11.00000 0.03840 0.03318 = 0.03526 0.00254 0.00562 0.00398 AFIX 23 H7A 2 0.976509 1.318905 0.135918 11.00000 -1.20000 H7B 2 0.921060 1.105088 0.089536 11.00000 -1.20000 AFIX 0 C8 1 0.906505 1.128258 0.212350 11.00000 0.03284 0.03856 = 0.04303 -0.00069 0.00862 0.00592 AFIX 43 H8 2 0.835393 1.184812 0.203444 11.00000 -1.20000 AFIX 0 C9 1 0.948795 1.022523 0.286117 11.00000 0.03230 0.03518 = 0.03745 -0.00414 0.01105 0.00039 C10 1 0.888291 0.989745 0.353927 11.00000 0.03522 0.04746 = 0.03911 -0.00633 0.01300 -0.00226 C11 1 0.908155 0.807559 0.407818 11.00000 0.05373 0.06100 = 0.05112 0.00681 0.02388 0.00356 AFIX 43 H11 2 0.961828 0.705525 0.402484 11.00000 -1.20000 AFIX 0 C12 1 0.849017 0.774825 0.469844 11.00000 0.06871 0.08158 = 0.05208 0.00720 0.02668 -0.01101 AFIX 43 H12 2 0.863351 0.650962 0.505197 11.00000 -1.20000 AFIX 0 C13 1 0.770257 0.922527 0.479318 11.00000 0.05453 0.09650 = 0.04743 -0.01993 0.02681 -0.02071 AFIX 43 H13 2 0.731194 0.900428 0.521040 11.00000 -1.20000 AFIX 0 C14 1 0.749331 1.104473 0.426428 11.00000 0.05357 0.09026 = 0.06283 -0.02072 0.03027 0.00422 AFIX 43 H14 2 0.695265 1.205143 0.432164 11.00000 -1.20000 AFIX 0 C15 1 0.807971 1.139453 0.364640 11.00000 0.05187 0.06161 = 0.05669 -0.00688 0.02408 0.00872 AFIX 43 H15 2 0.793485 1.264452 0.329916 11.00000 -1.20000 AFIX 0 O1 3 1.044557 0.690747 0.089918 11.00000 0.06621 0.04043 = 0.04350 -0.01037 0.01116 -0.00102 O2 3 1.199143 1.201955 0.291622 11.00000 0.03910 0.04774 = 0.04573 -0.00802 0.00615 -0.01145 HKLF 4 REM BA38M in P2(1)/n REM R1 = 0.0443 for 2535 Fo > 4sig(Fo) and 0.0487 for all 2830 data REM 155 parameters refined using 0 restraints END WGHT 0.0752 0.2196 REM Highest difference peak 0.284, deepest hole -0.223, 1-sigma level 0.046 Q1 1 1.1042 1.0691 0.2025 11.00000 0.05 0.28 Q2 1 1.0982 0.9938 0.2827 11.00000 0.05 0.27 Q3 1 0.9399 1.1308 0.1792 11.00000 0.05 0.25 Q4 1 0.9191 1.0058 0.3203 11.00000 0.05 0.25 Q5 1 1.0727 0.9248 0.1569 11.00000 0.05 0.24 ; _shelx_res_checksum 14818 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.05858(8) 0.79739(17) 0.15472(7) 0.0338(2) Uani 1 1 d . . . . . C2 C 1.05433(9) 0.70839(17) 0.24249(7) 0.0368(2) Uani 1 1 d . . . . . H2A H 1.1155 0.6087 0.2647 0.044 Uiso 1 1 calc R U . . . H2B H 0.9856 0.6306 0.2397 0.044 Uiso 1 1 calc R U . . . C3 C 1.06275(8) 0.91718(18) 0.29863(6) 0.0332(2) Uani 1 1 d . . . . . H3 H 1.0984 0.8888 0.3591 0.040 Uiso 1 1 calc R U . . . C4 C 1.12824(8) 1.07465(17) 0.25653(7) 0.0324(2) Uani 1 1 d . . . . . C5 C 1.08176(8) 1.04566(17) 0.16098(6) 0.0322(2) Uani 1 1 d . . . . . C6 C 1.15053(10) 1.1321(2) 0.10243(8) 0.0433(3) Uani 1 1 d . . . . . H6A H 1.1717 1.2824 0.1175 0.065 Uiso 1 1 calc R U . . . H6B H 1.1081 1.1264 0.0440 0.065 Uiso 1 1 calc R U . . . H6C H 1.2154 1.0424 0.1087 0.065 Uiso 1 1 calc R U . . . C7 C 0.96652(9) 1.16138(18) 0.14308(7) 0.0362(2) Uani 1 1 d . . . . . H7A H 0.9765 1.3189 0.1359 0.043 Uiso 1 1 calc R U . . . H7B H 0.9211 1.1051 0.0895 0.043 Uiso 1 1 calc R U . . . C8 C 0.90650(9) 1.12826(19) 0.21235(7) 0.0382(3) Uani 1 1 d . . . . . H8 H 0.8354 1.1848 0.2034 0.046 Uiso 1 1 calc R U . . . C9 C 0.94880(9) 1.02252(18) 0.28612(7) 0.0345(2) Uani 1 1 d . . . . . C10 C 0.88829(9) 0.9897(2) 0.35393(7) 0.0399(3) Uani 1 1 d . . . . . C11 C 0.90815(12) 0.8076(3) 0.40782(9) 0.0534(3) Uani 1 1 d . . . . . H11 H 0.9618 0.7055 0.4025 0.064 Uiso 1 1 calc R U . . . C12 C 0.84902(13) 0.7748(3) 0.46984(10) 0.0654(4) Uani 1 1 d . . . . . H12 H 0.8634 0.6510 0.5052 0.078 Uiso 1 1 calc R U . . . C13 C 0.77026(12) 0.9225(3) 0.47932(10) 0.0637(4) Uani 1 1 d . . . . . H13 H 0.7312 0.9004 0.5210 0.076 Uiso 1 1 calc R U . . . C14 C 0.74933(12) 1.1045(3) 0.42643(10) 0.0661(4) Uani 1 1 d . . . . . H14 H 0.6953 1.2051 0.4322 0.079 Uiso 1 1 calc R U . . . C15 C 0.80797(11) 1.1395(3) 0.36464(9) 0.0548(3) Uani 1 1 d . . . . . H15 H 0.7935 1.2645 0.3299 0.066 Uiso 1 1 calc R U . . . O1 O 1.04456(8) 0.69075(15) 0.08992(6) 0.0504(3) Uani 1 1 d . . . . . O2 O 1.19914(7) 1.20196(15) 0.29162(6) 0.0449(2) Uani 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 C1 0.0315(5) 0.0318(5) 0.0373(5) -0.0020(4) 0.0072(4) 0.0014(4) C2 0.0384(5) 0.0303(5) 0.0439(6) 0.0029(4) 0.0142(4) 0.0022(4) C3 0.0317(5) 0.0371(5) 0.0308(5) 0.0018(4) 0.0075(4) 0.0014(4) C4 0.0300(5) 0.0330(5) 0.0342(5) -0.0020(4) 0.0076(4) 0.0018(4) C5 0.0345(5) 0.0311(5) 0.0313(5) 0.0002(4) 0.0088(4) -0.0017(4) C6 0.0451(6) 0.0482(6) 0.0392(6) 0.0049(5) 0.0154(5) -0.0049(5) C7 0.0384(5) 0.0332(5) 0.0353(5) 0.0025(4) 0.0056(4) 0.0040(4) C8 0.0328(5) 0.0386(6) 0.0430(6) -0.0007(4) 0.0086(4) 0.0059(4) C9 0.0323(5) 0.0352(5) 0.0375(5) -0.0041(4) 0.0111(4) 0.0004(4) C10 0.0352(5) 0.0475(6) 0.0391(5) -0.0063(5) 0.0130(4) -0.0023(5) C11 0.0537(7) 0.0610(8) 0.0511(7) 0.0068(6) 0.0239(6) 0.0036(6) C12 0.0687(10) 0.0816(11) 0.0521(8) 0.0072(8) 0.0267(7) -0.0110(8) C13 0.0545(8) 0.0965(12) 0.0474(7) -0.0199(8) 0.0268(6) -0.0207(8) C14 0.0536(8) 0.0903(12) 0.0628(9) -0.0207(9) 0.0303(7) 0.0042(8) C15 0.0519(7) 0.0616(8) 0.0567(8) -0.0069(6) 0.0241(6) 0.0087(6) O1 0.0662(6) 0.0404(5) 0.0435(5) -0.0104(4) 0.0112(4) -0.0010(4) O2 0.0391(4) 0.0477(5) 0.0457(5) -0.0080(4) 0.0061(3) -0.0114(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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 O1 C1 C2 125.71(10) . . O1 C1 C5 124.73(10) . . C2 C1 C5 109.56(8) . . C1 C2 C3 103.94(8) . . C1 C2 H2A 111.0 . . C3 C2 H2A 111.0 . . C1 C2 H2B 111.0 . . C3 C2 H2B 111.0 . . H2A C2 H2B 109.0 . . C4 C3 C9 105.48(8) . . C4 C3 C2 102.68(8) . . C9 C3 C2 109.60(8) . . C4 C3 H3 112.8 . . C9 C3 H3 112.8 . . C2 C3 H3 112.8 . . O2 C4 C5 127.28(10) . . O2 C4 C3 127.33(10) . . C5 C4 C3 105.33(8) . . C6 C5 C4 117.06(9) . . C6 C5 C1 115.18(9) . . C4 C5 C1 101.56(8) . . C6 C5 C7 111.62(9) . . C4 C5 C7 104.12(8) . . C1 C5 C7 106.00(8) . . C5 C6 H6A 109.5 . . C5 C6 H6B 109.5 . . H6A C6 H6B 109.5 . . C5 C6 H6C 109.5 . . H6A C6 H6C 109.5 . . H6B C6 H6C 109.5 . . C8 C7 C5 114.12(9) . . C8 C7 H7A 108.7 . . C5 C7 H7A 108.7 . . C8 C7 H7B 108.7 . . C5 C7 H7B 108.7 . . H7A C7 H7B 107.6 . . C9 C8 C7 124.11(10) . . C9 C8 H8 117.9 . . C7 C8 H8 117.9 . . C8 C9 C10 123.58(10) . . C8 C9 C3 118.06(9) . . C10 C9 C3 118.25(9) . . C11 C10 C15 117.62(12) . . C11 C10 C9 121.32(11) . . C15 C10 C9 121.06(12) . . C10 C11 C12 121.01(14) . . C10 C11 H11 119.5 . . C12 C11 H11 119.5 . . C13 C12 C11 120.68(16) . . C13 C12 H12 119.7 . . C11 C12 H12 119.7 . . C12 C13 C14 119.18(13) . . C12 C13 H13 120.4 . . C14 C13 H13 120.4 . . C13 C14 C15 120.69(15) . . C13 C14 H14 119.7 . . C15 C14 H14 119.7 . . C14 C15 C10 120.81(15) . . C14 C15 H15 119.6 . . C10 C15 H15 119.6 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 O1 1.2005(13) . C1 C2 1.5223(15) . C1 C5 1.5258(14) . C2 C3 1.5391(15) . C2 H2A 0.9700 . C2 H2B 0.9700 . C3 C4 1.5171(14) . C3 C9 1.5276(14) . C3 H3 0.9800 . C4 O2 1.2046(13) . C4 C5 1.5138(14) . C5 C6 1.5134(14) . C5 C7 1.5630(14) . C6 H6A 0.9600 . C6 H6B 0.9600 . C6 H6C 0.9600 . C7 C8 1.4993(15) . C7 H7A 0.9700 . C7 H7B 0.9700 . C8 C9 1.3370(16) . C8 H8 0.9300 . C9 C10 1.4830(15) . C10 C11 1.3848(19) . C10 C15 1.3923(17) . C11 C12 1.3918(18) . C11 H11 0.9300 . C12 C13 1.364(2) . C12 H12 0.9300 . C13 C14 1.375(3) . C13 H13 0.9300 . C14 C15 1.3862(19) . C14 H14 0.9300 . C15 H15 0.9300 .