#------------------------------------------------------------------------------ #$Date: 2016-03-22 11:51:51 +0200 (Tue, 22 Mar 2016) $ #$Revision: 178920 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/11/49/4114990.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_4114990 loop_ _publ_author_name 'Ken Kokubo' 'Hiroshi Yamaguchi' 'Tatsuya Kawamoto' 'Takumi Oshima' _publ_section_title ; Substituent Effects on the Stereochemistry in the [2 + 2] Photocycloaddition Reaction of Homobenzoquinone Derivative with Variously Substituted Alkenes and Alkynes ; _journal_name_full 'Journal of the American Chemical Society' _journal_page_first 8912 _journal_page_last 8921 _journal_paper_doi 10.1021/ja025593n _journal_volume 124 _journal_year 2002 _chemical_compound_source 'Local laboratory' _chemical_formula_moiety 'C30 H28 O3' _chemical_formula_sum 'C30 H28 O3' _chemical_formula_weight 436.60 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_type_scat_source 'International Tables (1974)' _cell_angle_alpha 90.00 _cell_angle_beta 92.50(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 21.495(9) _cell_length_b 12.480(7) _cell_length_c 8.88(1) _cell_measurement_reflns_used 22 _cell_measurement_temperature 298 _cell_measurement_theta_max 12.4 _cell_measurement_theta_min 10.8 _cell_volume 2380(3) _computing_cell_refinement 'MXC(MAC Science)' _computing_data_collection 'MXC(MAC Science)' _computing_data_reduction Crystan _computing_molecular_graphics Crystan _computing_publication_material Crystan _computing_structure_refinement Crystan _computing_structure_solution Crystan _diffrn_measurement_device 'Mac Science MXC3' _diffrn_measurement_method theta/2theta _diffrn_orient_matrix_type standard _diffrn_orient_matrix_UB_11 0.04144 _diffrn_orient_matrix_UB_12 -0.03630 _diffrn_orient_matrix_UB_13 0.00918 _diffrn_orient_matrix_UB_21 0.02063 _diffrn_orient_matrix_UB_22 0.06705 _diffrn_orient_matrix_UB_23 -0.03368 _diffrn_orient_matrix_UB_31 0.00507 _diffrn_orient_matrix_UB_32 0.02465 _diffrn_orient_matrix_UB_33 0.10720 _diffrn_radiation_type 'Mo K-alpha' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.061 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 4853 _diffrn_reflns_theta_max 24.64 _diffrn_standards_decay_% 16.656 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.0721 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.218 _exptl_crystal_description Plate _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.28 _refine_diff_density_min -0.32 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.639 _refine_ls_hydrogen_treatment refall _refine_ls_number_parameters 388 _refine_ls_number_reflns 2080 _refine_ls_R_factor_obs 0.088 _refine_ls_shift/esd_max 0.0380 _refine_ls_shift/esd_mean 0.0028 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'Count statistics' _refine_ls_wR_factor_obs 0.103 _reflns_number_observed 2080 _reflns_number_total 3341 _reflns_observed_criterion refl_observed_if_I_>_2.00_sigma(I) _cod_data_source_file ja025593n_s2_2.cif _cod_data_source_block compound_exo-3e _cod_original_cell_volume 2379(3) _cod_original_sg_symbol_H-M 'P 21/c ' _cod_database_code 4114990 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z -X,+Y+0.5,-Z+0.5 +X,-Y+0.5,+Z+0.5 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 O2 0.069(3) 0.054(3) 0.123(4) 0.009(2) -0.007(3) 0.011(3) O20 0.091(4) 0.064(3) 0.196(7) 0.020(3) -0.030(4) -0.018(4) O30 0.069(4) 0.100(4) 0.131(5) -0.010(3) -0.014(3) -0.016(3) C1 0.054(4) 0.062(4) 0.063(4) 0.008(3) 0.000(3) -0.011(3) C3 0.064(4) 0.075(4) 0.055(4) 0.006(4) 0.006(3) -0.005(4) C4 0.061(4) 0.066(4) 0.060(4) 0.005(3) 0.003(3) -0.001(3) C5 0.062(4) 0.049(4) 0.056(4) -0.001(3) -0.002(3) -0.001(3) C6 0.065(4) 0.058(4) 0.060(4) 0.001(3) -0.002(3) 0.009(3) C7 0.073(5) 0.076(5) 0.064(5) -0.003(4) 0.007(4) -0.004(4) C8 0.085(6) 0.085(6) 0.060(5) -0.013(5) 0.017(4) -0.001(5) C9 0.097(6) 0.061(5) 0.067(5) -0.011(4) -0.003(4) 0.007(4) C10 0.073(5) 0.061(4) 0.062(4) 0.007(4) -0.005(4) -0.002(4) C11 0.056(4) 0.086(5) 0.058(4) 0.003(4) 0.011(3) -0.012(4) C12 0.076(5) 0.078(5) 0.086(5) -0.002(4) -0.002(4) 0.018(4) C13 0.096(8) 0.122(9) 0.113(7) -0.036(6) 0.012(6) 0.008(6) C14 0.085(7) 0.110(8) 0.108(7) -0.022(6) 0.011(6) 0.005(6) C15 0.048(5) 0.147(9) 0.087(6) 0.004(5) 0.003(4) -0.020(6) C16 0.059(5) 0.092(6) 0.077(5) 0.005(4) 0.001(4) -0.002(4) C17 0.066(4) 0.073(5) 0.066(4) 0.015(4) 0.000(3) -0.012(4) C18 0.080(6) 0.131(8) 0.088(6) 0.012(6) 0.016(5) -0.027(6) C19 0.077(5) 0.061(5) 0.079(5) 0.016(4) -0.019(4) -0.015(4) C21 0.090(6) 0.058(4) 0.058(4) 0.006(4) -0.013(4) -0.001(4) C22 0.094(6) 0.060(5) 0.077(5) 0.007(5) 0.002(5) 0.004(4) C23 0.060(4) 0.055(4) 0.059(4) -0.003(3) 0.008(3) 0.006(3) C24 0.073(5) 0.058(4) 0.059(4) 0.000(3) 0.012(3) -0.005(3) C25 0.089(6) 0.074(6) 0.083(6) 0.001(5) 0.020(5) -0.009(5) C26 0.064(4) 0.057(4) 0.059(4) 0.001(3) 0.007(3) -0.012(3) C27 0.078(5) 0.075(5) 0.076(5) -0.011(4) 0.008(4) 0.008(4) C28 0.063(5) 0.078(6) 0.110(6) -0.026(4) 0.004(5) -0.001(5) C29 0.054(4) 0.078(5) 0.097(6) 0.000(4) 0.005(4) -0.025(5) C31 0.063(6) 0.145(10) 0.166(12) -0.015(7) -0.023(6) -0.036(8) C32 0.073(6) 0.074(5) 0.103(6) 0.008(4) -0.014(5) 0.001(5) C33 0.071(5) 0.058(4) 0.093(5) -0.008(4) 0.000(4) 0.001(4) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type O2 0.6998(2) 0.1212(4) 0.4962(6) 0.082(3) 1.000 Uij O20 0.8420(3) -0.2184(4) 0.6634(9) 0.118(4) 1.000 Uij O30 0.4590(3) -0.1464(4) 0.1306(7) 0.101(4) 1.000 Uij C1 0.7311(3) 0.0505(6) 0.5503(7) 0.060(4) 1.000 Uij C3 0.7997(3) 0.0566(6) 0.5506(8) 0.065(4) 1.000 Uij C4 0.8411(3) 0.0561(5) 0.6937(7) 0.062(4) 1.000 Uij C5 0.8122(3) 0.0503(5) 0.8456(7) 0.056(4) 1.000 Uij C6 0.7683(3) 0.1270(5) 0.8843(8) 0.061(4) 1.000 Uij C7 0.7449(4) 0.1275(7) 1.0277(8) 0.071(5) 1.000 Uij C8 0.7646(4) 0.0516(7) 1.1290(9) 0.077(5) 1.000 Uij C9 0.8085(4) -0.0235(6) 1.0929(9) 0.075(5) 1.000 Uij C10 0.8315(4) -0.0236(6) 0.9506(8) 0.066(4) 1.000 Uij C11 0.8977(3) 0.1299(6) 0.7006(7) 0.066(4) 1.000 Uij C12 0.8951(4) 0.2339(6) 0.6442(9) 0.080(5) 1.000 Uij C13 0.9470(5) 0.3000(9) 0.6573(11) 0.110(7) 1.000 Uij C14 1.0015(5) 0.2628(9) 0.7211(12) 0.101(7) 1.000 Uij C15 1.0042(3) 0.1618(10) 0.7793(10) 0.094(6) 1.000 Uij C16 0.9531(3) 0.0935(7) 0.7692(8) 0.076(5) 1.000 Uij C17 0.8418(3) -0.0371(6) 0.5885(7) 0.069(4) 1.000 Uij C18 0.8973(5) -0.0600(9) 0.4918(12) 0.099(7) 1.000 Uij C19 0.8110(4) -0.1391(6) 0.6455(8) 0.073(5) 1.000 Uij C21 0.7429(4) -0.1398(5) 0.6769(8) 0.069(4) 1.000 Uij C22 0.7074(5) -0.2219(6) 0.5830(10) 0.077(5) 1.000 Uij C23 0.6869(3) -0.1322(5) 0.4718(7) 0.058(4) 1.000 Uij C24 0.7007(3) -0.0510(5) 0.6058(7) 0.063(4) 1.000 Uij C25 0.6434(5) -0.0263(8) 0.6939(12) 0.081(6) 1.000 Uij C26 0.6249(3) -0.1345(5) 0.3903(7) 0.060(4) 1.000 Uij C27 0.5828(4) -0.2196(6) 0.4045(9) 0.077(5) 1.000 Uij C28 0.5275(4) -0.2241(7) 0.3252(10) 0.084(5) 1.000 Uij C29 0.5111(3) -0.1470(6) 0.2195(10) 0.076(5) 1.000 Uij C31 0.4182(5) -0.2345(10) 0.1353(16) 0.125(8) 1.000 Uij C32 0.5523(4) -0.0601(7) 0.2052(11) 0.084(5) 1.000 Uij C33 0.6063(4) -0.0560(6) 0.2840(9) 0.074(5) 1.000 Uij H3 0.815(3) 0.101(5) 0.452(7) 0.07(2) 1.000 Uiso H6 0.755(2) 0.179(4) 0.806(6) 0.05(2) 1.000 Uiso H7 0.712(3) 0.184(5) 1.043(7) 0.07(2) 1.000 Uiso H8 0.754(3) 0.049(5) 1.229(8) 0.08(2) 1.000 Uiso H9 0.821(3) -0.076(6) 1.175(9) 0.10(2) 1.000 Uiso H10 0.867(3) -0.073(4) 0.930(6) 0.05(2) 1.000 Uiso H12 0.857(3) 0.259(5) 0.596(7) 0.13(3) 1.000 Uiso H13 0.944(4) 0.372(7) 0.621(9) 0.18(5) 1.000 Uiso H14 1.047(4) 0.294(6) 0.761(9) 0.11(3) 1.000 Uiso H15 1.042(3) 0.138(6) 0.830(9) 0.09(2) 1.000 Uiso H16 0.956(3) 0.022(5) 0.809(8) 0.12(3) 1.000 Uiso H18A 0.912(5) 0.002(7) 0.467(10) 0.10(4) 1.000 Uiso H18B 0.883(3) -0.105(6) 0.390(9) 0.09(2) 1.000 Uiso H18C 0.943(5) -0.046(8) 0.545(12) 0.15(4) 1.000 Uiso H21 0.746(2) -0.152(4) 0.782(6) 0.04(1) 1.000 Uiso H22A 0.729(4) -0.280(6) 0.538(8) 0.10(3) 1.000 Uiso H22B 0.673(3) -0.260(5) 0.637(7) 0.08(2) 1.000 Uiso H23 0.719(2) -0.119(4) 0.390(5) 0.03(1) 1.000 Uiso H25A 0.654(3) -0.002(5) 0.795(8) 0.07(2) 1.000 Uiso H25B 0.613(4) 0.014(7) 0.633(9) 0.11(3) 1.000 Uiso H25C 0.620(5) -0.093(8) 0.696(10) 0.14(4) 1.000 Uiso H27 0.595(3) -0.274(5) 0.487(7) 0.06(2) 1.000 Uiso H28 0.503(4) -0.288(6) 0.331(8) 0.10(3) 1.000 Uiso H31A 0.381(3) -0.234(5) 0.072(7) 0.13(3) 1.000 Uiso H31B 0.406(5) -0.240(8) 0.238(13) 0.18(6) 1.000 Uiso H31C 0.441(5) -0.297(8) 0.110(13) 0.14(4) 1.000 Uiso H32 0.536(3) -0.018(5) 0.125(7) 0.07(2) 1.000 Uiso H33 0.638(3) 0.001(6) 0.267(7) 0.08(2) 1.000 Uiso loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -4 10 6 3 1 6 4 2 1 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 C29 O30 C31 118.6(8) yes O2 C1 C3 120.4(7) yes O2 C1 C24 120.4(6) yes C3 C1 C24 119.0(6) yes C1 C3 C4 123.3(6) yes C1 C3 C17 123.4(7) yes C4 C3 C17 58.8(5) yes C3 C4 C5 119.9(6) yes C3 C4 C11 117.7(6) yes C3 C4 C17 60.3(5) yes C5 C4 C11 110.8(6) yes C5 C4 C17 122.4(6) yes C11 C4 C17 117.6(6) yes C4 C5 C6 119.4(6) yes C4 C5 C10 121.4(6) yes C6 C5 C10 119.0(6) yes C5 C6 C7 120.0(7) yes C6 C7 C8 119.4(8) yes C7 C8 C9 121.1(8) yes C8 C9 C10 119.2(8) yes C5 C10 C9 121.2(7) yes C4 C11 C12 121.9(7) yes C4 C11 C16 119.0(7) yes C12 C11 C16 119.1(7) yes C11 C12 C13 120.3(8) yes C12 C13 C14 120.3(10) yes C13 C14 C15 119.8(10) yes C14 C15 C16 121.4(9) yes C11 C16 C15 119.0(8) yes C3 C17 C4 60.9(5) yes C3 C17 C18 119.6(7) yes C3 C17 C19 117.1(6) yes C4 C17 C18 121.8(7) yes C4 C17 C19 115.0(6) yes C18 C17 C19 113.1(7) yes O20 C19 C17 119.0(7) yes O20 C19 C21 120.7(7) yes C17 C19 C21 120.3(7) yes C19 C21 C22 112.1(7) yes C19 C21 C24 118.5(6) yes C22 C21 C24 89.3(6) yes C21 C22 C23 89.1(6) yes C22 C23 C24 86.8(6) yes C22 C23 C26 121.5(6) yes C24 C23 C26 120.9(6) yes C1 C24 C21 118.7(6) yes C1 C24 C23 111.0(5) yes C1 C24 C25 111.6(6) yes C21 C24 C23 86.4(5) yes C21 C24 C25 114.0(7) yes C23 C24 C25 112.7(7) yes C23 C26 C27 122.4(6) yes C23 C26 C33 122.4(7) yes C27 C26 C33 115.0(7) yes C26 C27 C28 122.4(8) yes C27 C28 C29 121.2(8) yes O30 C29 C28 126.0(8) yes O30 C29 C32 116.8(8) yes C28 C29 C32 117.2(8) yes C29 C32 C33 121.1(8) yes C26 C33 C32 122.9(8) yes C1 C3 H3 110.8(32) yes C4 C3 H3 119.0(32) yes C17 C3 H3 112.2(32) yes C5 C6 H6 117.4(32) yes C7 C6 H6 122.6(32) yes C6 C7 H7 113.8(35) yes C8 C7 H7 126.7(35) yes C7 C8 H8 124.7(41) yes C9 C8 H8 113.9(41) yes C8 C9 H9 116.1(43) yes C10 C9 H9 124.7(43) yes C5 C10 H10 120.3(31) yes C9 C10 H10 118.1(31) yes C11 C12 H12 119.2(40) yes C13 C12 H12 120.5(40) yes C12 C13 H13 119.6(55) yes C14 C13 H13 120.1(55) yes C13 C14 H14 138.4(44) yes C15 C14 H14 100.8(43) yes C14 C15 H15 119.1(44) yes C16 C15 H15 119.5(45) yes C11 C16 H16 120.7(41) yes C15 C16 H16 120.2(41) yes C17 C18 H18A 106.4(64) yes C17 C18 H18B 111.4(37) yes C17 C18 H18C 116.0(56) yes H18A C18 H18B 109.2(72) yes H18A C18 H18C 68.9(82) yes H18B C18 H18C 131.0(66) yes C19 C21 H21 98.8(30) yes C22 C21 H21 116.3(30) yes C24 C21 H21 122.8(30) yes C21 C22 H22A 119.4(47) yes C21 C22 H22B 114.8(38) yes C23 C22 H22A 114.4(46) yes C23 C22 H22B 116.2(39) yes H22A C22 H22B 103.4(61) yes C22 C23 H23 112.7(26) yes C24 C23 H23 108.1(26) yes C26 C23 H23 105.9(27) yes C24 C25 H25A 112.7(39) yes C24 C25 H25B 110.9(51) yes C24 C25 H25C 105.9(58) yes H25A C25 H25B 118.3(62) yes H25A C25 H25C 110.3(67) yes H25B C25 H25C 96.9(77) yes C26 C27 H27 115.1(32) yes C28 C27 H27 122.2(32) yes C27 C28 H28 118.1(47) yes C29 C28 H28 119.9(47) yes O30 C31 H31A 118.7(39) yes O30 C31 H31B 106.1(65) yes O30 C31 H31C 107.6(65) yes H31A C31 H31B 107.5(77) yes H31A C31 H31C 107.6(78) yes H31B C31 H31C 109.1(94) yes C29 C32 H32 106.7(41) yes C33 C32 H32 131.6(42) yes C26 C33 H33 115.4(40) yes C32 C33 H33 121.6(40) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O2 C1 1.200(9) yes O20 C19 1.201(10) yes O30 C29 1.342(10) yes O30 C31 1.407(13) yes C1 C3 1.477(10) yes C1 C24 1.519(10) yes C3 C4 1.519(10) yes C3 C17 1.510(10) yes C4 C5 1.510(9) yes C4 C11 1.525(10) yes C4 C17 1.488(10) yes C5 C6 1.397(10) yes C5 C10 1.367(10) yes C6 C7 1.389(11) yes C7 C8 1.363(12) yes C8 C9 1.377(12) yes C9 C10 1.376(11) yes C11 C12 1.394(11) yes C11 C16 1.390(10) yes C12 C13 1.388(14) yes C13 C14 1.363(16) yes C14 C15 1.365(17) yes C15 C16 1.391(13) yes C17 C18 1.526(13) yes C17 C19 1.534(11) yes C19 C21 1.502(11) yes C21 C22 1.503(12) yes C21 C24 1.551(10) yes C22 C23 1.548(11) yes C23 C24 1.577(9) yes C23 C26 1.488(10) yes C24 C25 1.518(13) yes C26 C27 1.404(11) yes C26 C33 1.410(10) yes C27 C28 1.355(12) yes C28 C29 1.383(13) yes C29 C32 1.409(12) yes C32 C33 1.331(12) yes C3 H3 1.10(7) yes C6 H6 0.99(6) yes C7 H7 1.01(7) yes C8 H8 0.93(8) yes C9 H9 1.01(8) yes C10 H10 1.00(6) yes C12 H12 0.96(7) yes C13 H13 0.96(9) yes C14 H14 1.09(9) yes C15 H15 0.96(7) yes C16 H16 0.96(7) yes C18 H18A 0.87(9) yes C18 H18B 1.09(8) yes C18 H18C 1.09(12) yes C21 H21 0.94(6) yes C22 H22A 0.96(8) yes C22 H22B 1.02(7) yes C23 H23 1.04(5) yes C25 H25A 0.97(8) yes C25 H25B 0.97(9) yes C25 H25C 0.98(11) yes C27 H27 1.03(6) yes C28 H28 0.95(8) yes C31 H31A 0.96(7) yes C31 H31B 0.96(12) yes C31 H31C 0.96(11) yes C32 H32 0.95(7) yes C33 H33 1.00(8) yes