#------------------------------------------------------------------------------ #$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/26/1502680.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_1502680 loop_ _publ_author_name 'Cao, Deng-Ke' 'Sreevidya, Thekku Veedu' 'Botoshansky, Mark' 'Golden, Gilad' 'Benedict, Jason Brown' 'Kaftory, Menahem' _publ_section_title ; Kinetics of solid state photodimerization of 1,4-dimethyl-2-pyridinone in its molecular compound. ; _journal_issue 27 _journal_name_full 'The journal of physical chemistry. A' _journal_page_first 7377 _journal_page_last 7381 _journal_paper_doi 10.1021/jp101703q _journal_volume 114 _journal_year 2010 _chemical_formula_moiety 'C30 H22 O2 : 2(C7 H9 N O)' _chemical_formula_sum 'C44 H40 N2 O4' _chemical_formula_weight 660.78 _chemical_name_systematic ; 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol : 2(1,4-dimethyl-2-pyridinone) ; _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_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 67.875(2) _cell_angle_beta 84.032(2) _cell_angle_gamma 67.981(2) _cell_formula_units_Z 1 _cell_length_a 8.4124(7) _cell_length_b 10.7275(10) _cell_length_c 11.4652(10) _cell_measurement_reflns_used 1943 _cell_measurement_temperature 280(2) _cell_measurement_theta_max 26.11 _cell_measurement_theta_min 2.22 _cell_volume 887.73(14) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 280(2) _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 8439 _diffrn_reflns_theta_full 28.36 _diffrn_reflns_theta_max 28.36 _diffrn_reflns_theta_min 1.92 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 350 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.169 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.035 _refine_ls_extinction_coef 0.029(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 232 _refine_ls_number_reflns 4421 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.001 _refine_ls_R_factor_all 0.0833 _refine_ls_R_factor_gt 0.0438 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+0.0460P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1089 _refine_ls_wR_factor_ref 0.1301 _reflns_number_gt 2670 _reflns_number_total 4421 _reflns_threshold_expression >2sigma(I) _cod_data_source_file jp101703q_si_004.cif _cod_data_source_block c:\Cao18(280K) _cod_original_sg_symbol_H-M P-1 _cod_database_code 1502680 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 0.63609(14) 0.73968(12) -0.33375(9) 0.0471(3) Uani 1 1 d . H1 H 0.705(2) 0.650(2) -0.3177(15) 0.056 Uiso 1 1 d . C1 C 0.52662(18) 0.55241(14) -0.04351(13) 0.0383(3) Uani 1 1 d . C2 C 0.57292(17) 0.64294(14) -0.11906(13) 0.0380(3) Uani 1 1 d . C3 C 0.62013(17) 0.75937(14) -0.21677(12) 0.0347(3) Uani 1 1 d . C4 C 0.78527(17) 0.76621(14) -0.17986(13) 0.0380(3) Uani 1 1 d . C5 C 0.86473(19) 0.68866(17) -0.06109(15) 0.0469(4) Uani 1 1 d . H5 H 0.8213 0.6244 -0.0007 0.056 Uiso 1 1 calc R C6 C 1.0093(2) 0.7063(2) -0.03138(19) 0.0645(5) Uani 1 1 d . H6 H 1.0622 0.6543 0.0487 0.077 Uiso 1 1 calc R C7 C 1.0732(2) 0.8005(2) -0.1206(2) 0.0773(6) Uani 1 1 d . H7 H 1.1692 0.8131 -0.1007 0.093 Uiso 1 1 calc R C8 C 0.9965(3) 0.8765(2) -0.2390(2) 0.0810(6) Uani 1 1 d . H8 H 1.0409 0.9402 -0.2992 0.097 Uiso 1 1 calc R C9 C 0.8540(2) 0.85911(19) -0.26912(17) 0.0608(5) Uani 1 1 d . H9 H 0.8036 0.9101 -0.3500 0.073 Uiso 1 1 calc R C10 C 0.47313(17) 0.90318(14) -0.23253(12) 0.0361(3) Uani 1 1 d . C11 C 0.3820(2) 0.99138(16) -0.34574(14) 0.0460(4) Uani 1 1 d . H11 H 0.4100 0.9641 -0.4154 0.055 Uiso 1 1 calc R C12 C 0.2491(2) 1.12033(18) -0.35619(16) 0.0588(4) Uani 1 1 d . H12 H 0.1897 1.1798 -0.4332 0.071 Uiso 1 1 calc R C13 C 0.2047(2) 1.16064(18) -0.25355(18) 0.0599(5) Uani 1 1 d . H13 H 0.1145 1.2465 -0.2604 0.072 Uiso 1 1 calc R C14 C 0.2951(2) 1.07280(18) -0.13992(17) 0.0582(4) Uani 1 1 d . H14 H 0.2655 1.0995 -0.0700 0.070 Uiso 1 1 calc R C15 C 0.4287(2) 0.94597(17) -0.12992(14) 0.0469(4) Uani 1 1 d . H15 H 0.4900 0.8882 -0.0534 0.056 Uiso 1 1 calc R O2 O 0.18891(17) 0.54615(12) 0.29525(11) 0.0684(4) Uani 1 1 d . N1 N 0.29170(19) 0.69846(16) 0.32708(14) 0.0604(4) Uani 1 1 d . C16 C 0.2290(2) 0.58858(17) 0.37177(16) 0.0510(4) Uani 1 1 d . C17 C 0.2117(2) 0.53389(18) 0.50356(16) 0.0574(4) Uani 1 1 d . H17 H 0.1667 0.4612 0.5369 0.069 Uiso 1 1 calc R C18 C 0.2570(2) 0.58152(19) 0.58374(16) 0.0618(5) Uani 1 1 d . C19 C 0.3267(3) 0.6904(2) 0.5320(2) 0.0738(6) Uani 1 1 d . H19 H 0.3623 0.7243 0.5842 0.089 Uiso 1 1 calc R C20 C 0.3416(3) 0.7452(2) 0.4067(2) 0.0763(6) Uani 1 1 d . H20 H 0.3874 0.8174 0.3735 0.092 Uiso 1 1 calc R C21 C 0.3023(3) 0.7662(3) 0.19021(19) 0.0965(7) Uani 1 1 d . H21A H 0.1888 0.8235 0.1525 0.145 Uiso 1 1 calc R H21B H 0.3568 0.6925 0.1554 0.145 Uiso 1 1 calc R H21C H 0.3682 0.8268 0.1732 0.145 Uiso 1 1 calc R C22 C 0.2360(4) 0.5204(3) 0.72344(18) 0.0998(8) Uani 1 1 d . H22A H 0.2637 0.4181 0.7502 0.150 Uiso 1 1 calc R H22B H 0.1194 0.5656 0.7422 0.150 Uiso 1 1 calc R H22C H 0.3115 0.5385 0.7670 0.150 Uiso 1 1 calc R 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 0.0611(7) 0.0422(6) 0.0423(6) -0.0198(5) 0.0042(5) -0.0196(5) C1 0.0374(8) 0.0339(7) 0.0462(8) -0.0146(6) 0.0036(6) -0.0161(6) C2 0.0383(8) 0.0339(7) 0.0442(7) -0.0140(6) 0.0029(6) -0.0162(6) C3 0.0387(7) 0.0330(7) 0.0353(7) -0.0120(5) 0.0044(5) -0.0174(6) C4 0.0352(8) 0.0327(7) 0.0496(8) -0.0182(6) 0.0067(6) -0.0141(6) C5 0.0418(9) 0.0481(9) 0.0558(9) -0.0250(7) 0.0027(7) -0.0157(7) C6 0.0439(10) 0.0739(13) 0.0876(13) -0.0489(11) -0.0092(9) -0.0116(9) C7 0.0398(10) 0.0768(14) 0.140(2) -0.0616(14) 0.0042(11) -0.0262(10) C8 0.0562(12) 0.0714(13) 0.1240(18) -0.0273(13) 0.0135(12) -0.0434(11) C9 0.0532(10) 0.0538(10) 0.0742(11) -0.0116(8) 0.0068(8) -0.0314(9) C10 0.0367(8) 0.0321(7) 0.0422(7) -0.0112(6) 0.0041(6) -0.0186(6) C11 0.0477(9) 0.0425(8) 0.0445(8) -0.0086(6) 0.0011(6) -0.0197(7) C12 0.0541(10) 0.0436(9) 0.0625(10) -0.0018(8) -0.0084(8) -0.0155(8) C13 0.0469(10) 0.0386(9) 0.0858(13) -0.0192(9) 0.0003(9) -0.0098(8) C14 0.0552(10) 0.0524(10) 0.0737(11) -0.0355(9) 0.0093(8) -0.0160(8) C15 0.0479(9) 0.0429(8) 0.0506(8) -0.0198(7) -0.0003(7) -0.0142(7) O2 0.0857(9) 0.0538(7) 0.0702(8) -0.0343(6) -0.0133(6) -0.0144(7) N1 0.0620(9) 0.0576(9) 0.0687(9) -0.0303(7) 0.0096(7) -0.0240(8) C16 0.0502(9) 0.0391(8) 0.0629(10) -0.0254(8) -0.0072(7) -0.0061(7) C17 0.0732(12) 0.0415(9) 0.0588(10) -0.0179(7) -0.0068(8) -0.0204(9) C18 0.0696(12) 0.0469(10) 0.0645(11) -0.0258(8) -0.0132(9) -0.0071(9) C19 0.0770(14) 0.0711(13) 0.0916(15) -0.0456(12) -0.0172(11) -0.0250(11) C20 0.0747(14) 0.0746(14) 0.1026(16) -0.0436(12) 0.0073(11) -0.0415(12) C21 0.120(2) 0.0958(18) 0.0765(14) -0.0295(13) 0.0311(13) -0.0514(16) C22 0.147(2) 0.0804(16) 0.0628(13) -0.0287(11) -0.0160(13) -0.0243(16) 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' 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_3 C3 O1 H1 105.5(10) . C2 C1 C1 179.8(2) 2_665 C1 C2 C3 176.56(15) . O1 C3 C2 109.73(10) . O1 C3 C4 110.54(11) . C2 C3 C4 112.15(11) . O1 C3 C10 107.91(11) . C2 C3 C10 107.67(11) . C4 C3 C10 108.70(10) . C5 C4 C9 118.87(14) . C5 C4 C3 123.29(12) . C9 C4 C3 117.80(13) . C4 C5 C6 120.38(16) . C4 C5 H5 119.8 . C6 C5 H5 119.8 . C7 C6 C5 119.66(18) . C7 C6 H6 120.2 . C5 C6 H6 120.2 . C6 C7 C8 120.34(17) . C6 C7 H7 119.8 . C8 C7 H7 119.8 . C7 C8 C9 120.29(18) . C7 C8 H8 119.9 . C9 C8 H8 119.9 . C8 C9 C4 120.44(17) . C8 C9 H9 119.8 . C4 C9 H9 119.8 . C11 C10 C15 118.72(14) . C11 C10 C3 122.06(12) . C15 C10 C3 119.22(12) . C10 C11 C12 120.42(15) . C10 C11 H11 119.8 . C12 C11 H11 119.8 . C13 C12 C11 120.35(15) . C13 C12 H12 119.8 . C11 C12 H12 119.8 . C12 C13 C14 119.54(16) . C12 C13 H13 120.2 . C14 C13 H13 120.2 . C15 C14 C13 120.17(16) . C15 C14 H14 119.9 . C13 C14 H14 119.9 . C14 C15 C10 120.79(15) . C14 C15 H15 119.6 . C10 C15 H15 119.6 . C20 N1 C16 121.20(16) . C20 N1 C21 120.29(18) . C16 N1 C21 118.51(15) . O2 C16 N1 119.08(15) . O2 C16 C17 125.00(16) . N1 C16 C17 115.91(14) . C18 C17 C16 123.56(17) . C18 C17 H17 118.2 . C16 C17 H17 118.2 . C17 C18 C19 117.46(17) . C17 C18 C22 121.77(19) . C19 C18 C22 120.77(17) . C20 C19 C18 119.80(16) . C20 C19 H19 120.1 . C18 C19 H19 120.1 . C19 C20 N1 121.99(18) . C19 C20 H20 119.0 . N1 C20 H20 119.0 . N1 C21 H21A 109.5 . N1 C21 H21B 109.5 . H21A C21 H21B 109.5 . N1 C21 H21C 109.5 . H21A C21 H21C 109.5 . H21B C21 H21C 109.5 . C18 C22 H22A 109.5 . C18 C22 H22B 109.5 . H22A C22 H22B 109.5 . C18 C22 H22C 109.5 . H22A C22 H22C 109.5 . H22B C22 H22C 109.5 . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C3 1.4199(15) . O1 H1 0.872(18) . C1 C2 1.1938(18) . C1 C1 1.378(3) 2_665 C2 C3 1.4826(18) . C3 C4 1.5286(19) . C3 C10 1.5323(19) . C4 C5 1.383(2) . C4 C9 1.384(2) . C5 C6 1.393(2) . C5 H5 0.9300 . C6 C7 1.368(3) . C6 H6 0.9300 . C7 C8 1.371(3) . C7 H7 0.9300 . C8 C9 1.376(2) . C8 H8 0.9300 . C9 H9 0.9300 . C10 C11 1.3803(19) . C10 C15 1.3861(19) . C11 C12 1.386(2) . C11 H11 0.9300 . C12 C13 1.372(2) . C12 H12 0.9300 . C13 C14 1.381(2) . C13 H13 0.9300 . C14 C15 1.375(2) . C14 H14 0.9300 . C15 H15 0.9300 . O2 C16 1.2522(17) . N1 C20 1.358(2) . N1 C16 1.373(2) . N1 C21 1.469(2) . C16 C17 1.414(2) . C17 C18 1.351(2) . C17 H17 0.9300 . C18 C19 1.406(3) . C18 C22 1.505(3) . C19 C20 1.344(3) . C19 H19 0.9300 . C20 H20 0.9300 . C21 H21A 0.9600 . C21 H21B 0.9600 . C21 H21C 0.9600 . C22 H22A 0.9600 . C22 H22B 0.9600 . C22 H22C 0.9600 .