#------------------------------------------------------------------------------ #$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/26/1502683.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_1502683 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 : C14 H18 N2 O2' _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 : dimer of 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 65.5020(10) _cell_angle_beta 86.0650(10) _cell_angle_gamma 66.7450(10) _cell_formula_units_Z 1 _cell_length_a 8.3944(2) _cell_length_b 10.8552(3) _cell_length_c 11.3656(3) _cell_measurement_reflns_used 2421 _cell_measurement_temperature 230(2) _cell_measurement_theta_max 27.15 _cell_measurement_theta_min 2.29 _cell_volume 860.25(4) _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 230(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_max 11 _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 -15 _diffrn_reflns_number 16883 _diffrn_reflns_theta_full 28.07 _diffrn_reflns_theta_max 28.07 _diffrn_reflns_theta_min 1.98 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 350 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.260 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.038 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 232 _refine_ls_number_reflns 4185 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.937 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0419 _refine_ls_shift/su_max 0.081 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0786P)^2^+0.2206P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1156 _refine_ls_wR_factor_ref 0.1287 _reflns_number_gt 3347 _reflns_number_total 4185 _reflns_threshold_expression >2sigma(I) _cod_data_source_file jp101703q_si_007.cif _cod_data_source_block c:\Cao18(230K)(100) _cod_original_sg_symbol_H-M P-1 _cod_database_code 1502683 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 0.60799(13) 0.76735(11) -0.34098(8) 0.0337(2) Uani 1 1 d . C1 C 0.52153(15) 0.55603(13) -0.04393(12) 0.0278(2) Uani 1 1 d . C2 C 0.56033(15) 0.65284(13) -0.12039(11) 0.0270(2) Uani 1 1 d . C3 C 0.59712(15) 0.77699(12) -0.21944(11) 0.0242(2) Uani 1 1 d . C4 C 0.76530(15) 0.78062(13) -0.17909(12) 0.0269(2) Uani 1 1 d . C5 C 0.86188(16) 0.68740(15) -0.05881(13) 0.0340(3) Uani 1 1 d . H5 H 0.8278 0.6156 0.0014 0.041 Uiso 1 1 calc R C6 C 1.01062(19) 0.70047(19) -0.02712(18) 0.0486(4) Uani 1 1 d . H6 H 1.0750 0.6376 0.0541 0.058 Uiso 1 1 calc R C7 C 1.0616(2) 0.8059(2) -0.1157(2) 0.0587(5) Uani 1 1 d . H7 H 1.1601 0.8150 -0.0945 0.070 Uiso 1 1 calc R C8 C 0.9664(2) 0.8984(2) -0.2365(2) 0.0603(5) Uani 1 1 d . H8 H 1.0018 0.9693 -0.2967 0.072 Uiso 1 1 calc R C9 C 0.8187(2) 0.88654(17) -0.26901(16) 0.0435(3) Uani 1 1 d . H9 H 0.7553 0.9492 -0.3506 0.052 Uiso 1 1 calc R C10 C 0.44305(15) 0.92148(12) -0.23604(12) 0.0276(2) Uani 1 1 d . C11 C 0.33878(18) 1.01636(15) -0.35362(14) 0.0383(3) Uani 1 1 d . H11 H 0.3634 0.9947 -0.4256 0.046 Uiso 1 1 calc R C12 C 0.1970(2) 1.14429(16) -0.36361(18) 0.0519(4) Uani 1 1 d . H12 H 0.1272 1.2081 -0.4426 0.062 Uiso 1 1 calc R C13 C 0.1593(2) 1.17698(17) -0.2575(2) 0.0547(5) Uani 1 1 d . H13 H 0.0632 1.2616 -0.2644 0.066 Uiso 1 1 calc R C14 C 0.2650(2) 1.08351(17) -0.14054(19) 0.0507(4) Uani 1 1 d . H14 H 0.2405 1.1058 -0.0689 0.061 Uiso 1 1 calc R C15 C 0.40704(18) 0.95678(15) -0.13006(14) 0.0370(3) Uani 1 1 d . H15 H 0.4787 0.8950 -0.0517 0.044 Uiso 1 1 calc R O2 O 0.23336(12) 0.52131(11) 0.30753(10) 0.0404(2) Uani 1 1 d . N1 N 0.36460(15) 0.65419(12) 0.33833(10) 0.0342(2) Uani 1 1 d . C16 C 0.30836(16) 0.54518(14) 0.38055(13) 0.0318(3) Uani 1 1 d . C17B C 0.34244(17) 0.45202(14) 0.52725(12) 0.0322(3) Uani 1 1 d . H17 H 0.2655 0.3991 0.5515 0.039 Uiso 1 1 calc R C18 C 0.29569(17) 0.55447(15) 0.59492(13) 0.0348(3) Uani 1 1 d . C19 C 0.35680(17) 0.65912(14) 0.54876(13) 0.0337(3) Uani 1 1 d . H19 H 0.3376 0.7246 0.5863 0.040 Uiso 1 1 calc R C20B C 0.45909(17) 0.66816(14) 0.43257(12) 0.0324(3) Uani 1 1 d . H20 H 0.4610 0.7667 0.3921 0.039 Uiso 1 1 calc R C21 C 0.3528(2) 0.74392(18) 0.19945(14) 0.0485(4) Uani 1 1 d . H21A H 0.2323 0.8018 0.1645 0.073 Uiso 1 1 calc R H21B H 0.4076 0.6806 0.1565 0.073 Uiso 1 1 calc R H21C H 0.4107 0.8086 0.1858 0.073 Uiso 1 1 calc R C22 C 0.1887(2) 0.5301(2) 0.70678(16) 0.0521(4) Uani 1 1 d . H22A H 0.2465 0.4311 0.7727 0.078 Uiso 1 1 calc R H22B H 0.0760 0.5440 0.6770 0.078 Uiso 1 1 calc R H22C H 0.1751 0.5995 0.7423 0.078 Uiso 1 1 calc R H1 H 0.673(3) 0.673(2) -0.3255(19) 0.063 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 0.0466(5) 0.0341(5) 0.0266(4) -0.0146(4) 0.0064(4) -0.0208(4) C1 0.0265(5) 0.0245(5) 0.0327(6) -0.0113(5) 0.0057(4) -0.0119(5) C2 0.0260(5) 0.0245(5) 0.0303(6) -0.0103(5) 0.0045(4) -0.0115(4) C3 0.0283(5) 0.0232(5) 0.0234(5) -0.0087(4) 0.0047(4) -0.0140(4) C4 0.0261(5) 0.0279(6) 0.0344(6) -0.0178(5) 0.0086(5) -0.0141(4) C5 0.0296(6) 0.0377(7) 0.0375(7) -0.0205(5) 0.0037(5) -0.0115(5) C6 0.0292(7) 0.0593(9) 0.0653(10) -0.0424(8) -0.0037(6) -0.0071(6) C7 0.0301(7) 0.0714(11) 0.1050(15) -0.0604(11) 0.0118(8) -0.0260(8) C8 0.0470(9) 0.0576(10) 0.0972(15) -0.0368(10) 0.0234(9) -0.0393(8) C9 0.0421(8) 0.0408(8) 0.0526(8) -0.0154(7) 0.0113(6) -0.0270(6) C10 0.0271(5) 0.0229(5) 0.0331(6) -0.0080(5) 0.0053(5) -0.0147(4) C11 0.0361(7) 0.0330(7) 0.0387(7) -0.0051(5) -0.0007(5) -0.0172(5) C12 0.0355(7) 0.0300(7) 0.0681(10) 0.0008(7) -0.0092(7) -0.0125(6) C13 0.0315(7) 0.0295(7) 0.0954(13) -0.0220(8) 0.0106(8) -0.0101(6) C14 0.0444(8) 0.0407(8) 0.0741(11) -0.0339(8) 0.0204(8) -0.0160(7) C15 0.0372(7) 0.0323(6) 0.0419(7) -0.0171(6) 0.0089(5) -0.0136(5) O2 0.0379(5) 0.0414(5) 0.0473(6) -0.0276(5) -0.0046(4) -0.0103(4) N1 0.0417(6) 0.0321(5) 0.0282(5) -0.0112(4) 0.0005(4) -0.0154(5) C16 0.0310(6) 0.0315(6) 0.0364(6) -0.0199(5) 0.0021(5) -0.0099(5) C17B 0.0353(6) 0.0329(6) 0.0364(6) -0.0173(5) 0.0072(5) -0.0191(5) C18 0.0362(7) 0.0380(7) 0.0345(6) -0.0196(5) 0.0071(5) -0.0153(5) C19 0.0359(6) 0.0334(6) 0.0381(7) -0.0223(5) 0.0041(5) -0.0123(5) C20B 0.0399(7) 0.0265(6) 0.0347(6) -0.0141(5) 0.0029(5) -0.0158(5) C21 0.0622(10) 0.0444(8) 0.0309(7) -0.0095(6) 0.0012(6) -0.0200(7) C22 0.0567(9) 0.0604(10) 0.0496(9) -0.0314(8) 0.0247(8) -0.0280(8) 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_1 _geom_angle_site_symmetry_3 C3 O1 H1 107.6(13) . . C2 C1 C1 179.49(17) . 2_665 C1 C2 C3 176.38(12) . . O1 C3 C2 109.91(9) . . O1 C3 C10 108.17(9) . . C2 C3 C10 107.59(9) . . O1 C3 C4 109.80(9) . . C2 C3 C4 112.40(9) . . C10 C3 C4 108.85(9) . . C5 C4 C9 119.37(12) . . C5 C4 C3 123.47(10) . . C9 C4 C3 117.15(11) . . C4 C5 C6 120.32(13) . . C4 C5 H5 119.8 . . C6 C5 H5 119.8 . . C7 C6 C5 120.00(15) . . C7 C6 H6 120.0 . . C5 C6 H6 120.0 . . C6 C7 C8 119.89(13) . . C6 C7 H7 120.1 . . C8 C7 H7 120.1 . . C9 C8 C7 120.64(16) . . C9 C8 H8 119.7 . . C7 C8 H8 119.7 . . C8 C9 C4 119.79(15) . . C8 C9 H9 120.1 . . C4 C9 H9 120.1 . . C11 C10 C15 119.51(12) . . C11 C10 C3 121.53(11) . . C15 C10 C3 118.96(11) . . C10 C11 C12 119.75(15) . . C10 C11 H11 120.1 . . C12 C11 H11 120.1 . . C13 C12 C11 120.53(15) . . C13 C12 H12 119.7 . . C11 C12 H12 119.7 . . C12 C13 C14 119.79(14) . . C12 C13 H13 120.1 . . C14 C13 H13 120.1 . . C13 C14 C15 120.05(16) . . C13 C14 H14 120.0 . . C15 C14 H14 120.0 . . C14 C15 C10 120.34(14) . . C14 C15 H15 119.8 . . C10 C15 H15 119.8 . . C16 N1 C21 120.26(12) . . C16 N1 C20B 118.73(10) . . C21 N1 C20B 120.49(11) . . O2 C16 N1 123.31(12) . . O2 C16 C17B 121.99(12) . . N1 C16 C17B 114.70(10) . . C18 C17B C16 108.76(10) . . C18 C17B C20B 112.91(10) . 2_666 C16 C17B C20B 110.34(10) . 2_666 C18 C17B H17 108.2 . . C16 C17B H17 108.2 . . C20B C17B H17 108.2 2_666 . C19 C18 C22 125.42(13) . . C19 C18 C17B 115.58(11) . . C22 C18 C17B 118.99(12) . . C18 C19 C20B 117.56(11) . . C18 C19 H19 121.2 . . C20B C19 H19 121.2 . . N1 C20B C19 107.97(10) . . N1 C20B C17B 112.50(10) . 2_666 C19 C20B C17B 112.49(10) . 2_666 N1 C20B H20 107.9 . . C19 C20B H20 107.9 . . C17B C20B H20 107.9 2_666 . 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 1.4221(14) . O1 H1 0.90(2) . C1 C2 1.1999(16) . C1 C1 1.378(2) 2_665 C2 C3 1.4838(15) . C3 C10 1.5344(16) . C3 C4 1.5338(15) . C4 C5 1.3810(18) . C4 C9 1.3917(17) . C5 C6 1.3974(19) . C5 H5 0.9300 . C6 C7 1.370(3) . C6 H6 0.9300 . C7 C8 1.381(3) . C7 H7 0.9300 . C8 C9 1.385(2) . C8 H8 0.9300 . C9 H9 0.9300 . C10 C11 1.3856(18) . C10 C15 1.3894(18) . C11 C12 1.393(2) . C11 H11 0.9300 . C12 C13 1.376(3) . C12 H12 0.9300 . C13 C14 1.384(3) . C13 H13 0.9300 . C14 C15 1.385(2) . C14 H14 0.9300 . C15 H15 0.9300 . O2 C16 1.2374(15) . N1 C16 1.3389(17) . N1 C21 1.4561(17) . N1 C20B 1.4648(16) . C16 C17B 1.5242(18) . C17B C18 1.5185(18) . C17B C20B 1.6063(18) 2_666 C17B H17 0.9800 . C18 C19 1.3257(19) . C18 C22 1.4983(19) . C19 C20B 1.5147(18) . C19 H19 0.9300 . C20B C17B 1.6063(18) 2_666 C20B H20 0.9800 . C21 H21A 0.9600 . C21 H21B 0.9600 . C21 H21C 0.9600 . C22 H22A 0.9600 . C22 H22B 0.9600 . C22 H22C 0.9600 .