#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/70/2207039.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2207039 loop_ _publ_author_name 'Wang, Yu-Cheng' 'Wang, Xiang-Shan' 'Zeng, Zhao-Sen' 'Shi, Da-Qing' _publ_section_title ; Ethyl 5-cyano-4-(2,3-dimethoxyphenyl)-2-methyl-6-oxopyridine-3-carboxylate ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3261 _journal_page_last o3263 _journal_paper_doi 10.1107/S1600536805028679 _journal_volume 61 _journal_year 2005 _chemical_formula_moiety 'C18 H18 N2 O5' _chemical_formula_sum 'C18 H18 N2 O5' _chemical_formula_weight 342.34 _chemical_melting_point 514.0(10) _chemical_name_systematic ; Ethyl 2-methyl-4-(2,3-dimethoxylphenyl)-5-cyano-6-oxo- pyridin-3-carboxylate ; _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_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 100.143(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 15.2031(14) _cell_length_b 7.5946(7) _cell_length_c 15.1270(14) _cell_measurement_reflns_used 2339 _cell_measurement_temperature 292(2) _cell_measurement_theta_max 25.02 _cell_measurement_theta_min 2.72 _cell_volume 1719.3(3) _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 292(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _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 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 8803 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 2.72 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 720 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.265 _refine_diff_density_min -0.157 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 3379 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.070 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0466 _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^)+(0.0722P)^2^+0.1609P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1299 _refine_ls_wR_factor_ref 0.1372 _reflns_number_gt 2559 _reflns_number_total 3379 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob6584.cif _cod_data_source_block I _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 The following automatic conversions were performed: '_chemical_melting_point' value '513-515' was changed to '514.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '513-515' was changed to '514.0(10)' - the average value was taken and precision was estimated. '_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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M P21/c _cod_database_code 2207039 _cod_database_fobs_code 2207039 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_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol C1 0.40899(10) 1.3222(2) 0.43955(11) 0.0430(4) Uani d . 1 C C2 0.34531(10) 1.1906(2) 0.40264(11) 0.0412(4) Uani d . 1 C C3 0.32290(10) 1.0534(2) 0.45385(11) 0.0405(4) Uani d . 1 C C4 0.36887(11) 1.0329(2) 0.54334(11) 0.0456(4) Uani d . 1 C C5 0.43235(11) 1.1546(2) 0.57887(12) 0.0464(4) Uani d . 1 C C6 0.30640(11) 1.2085(2) 0.30983(12) 0.0441(4) Uani d . 1 C C7 0.35129(12) 0.8795(3) 0.59942(12) 0.0541(5) Uani d . 1 C C8 0.23996(17) 0.7002(3) 0.64431(16) 0.0776(7) Uani d . 1 C H8A 0.2571 0.7082 0.7091 0.093 Uiso calc R 1 H H8B 0.2694 0.5987 0.6237 0.093 Uiso calc R 1 H C9 0.14130(17) 0.6825(3) 0.61880(18) 0.0881(8) Uani d . 1 C H9A 0.1221 0.5777 0.6454 0.132 Uiso calc R 1 H H9B 0.1252 0.6751 0.5546 0.132 Uiso calc R 1 H H9C 0.1129 0.7832 0.6399 0.132 Uiso calc R 1 H C10 0.48522(13) 1.1515(3) 0.67227(13) 0.0631(5) Uani d . 1 C H10A 0.5248 1.2509 0.6807 0.095 Uiso calc R 1 H H10B 0.5195 1.0448 0.6812 0.095 Uiso calc R 1 H H10C 0.4453 1.1569 0.7148 0.095 Uiso calc R 1 H C11 0.25205(10) 0.9258(2) 0.41475(10) 0.0405(4) Uani d . 1 C C12 0.16453(10) 0.9831(2) 0.39121(10) 0.0384(4) Uani d . 1 C C13 0.09645(11) 0.8634(2) 0.35838(11) 0.0444(4) Uani d . 1 C C14 0.11747(13) 0.6886(2) 0.34890(13) 0.0551(5) Uani d . 1 C H14A 0.0727 0.6083 0.3269 0.066 Uiso calc R 1 H C15 0.20513(14) 0.6326(3) 0.37206(14) 0.0597(5) Uani d . 1 C H15A 0.2188 0.5145 0.3654 0.072 Uiso calc R 1 H C16 0.27223(12) 0.7487(2) 0.40471(13) 0.0524(5) Uani d . 1 C H16A 0.3309 0.7094 0.4201 0.063 Uiso calc R 1 H C17 0.11538(15) 1.1994(3) 0.48155(16) 0.0698(6) Uani d . 1 C H17A 0.1024 1.3230 0.4830 0.105 Uiso calc R 1 H H17B 0.1618 1.1702 0.5311 0.105 Uiso calc R 1 H H17C 0.0626 1.1330 0.4859 0.105 Uiso calc R 1 H C18 -0.05858(13) 0.8161(3) 0.30424(15) 0.0657(6) Uani d . 1 C H18A -0.1137 0.8807 0.2921 0.099 Uiso calc R 1 H H18B -0.0627 0.7266 0.3481 0.099 Uiso calc R 1 H H18C -0.0475 0.7622 0.2498 0.099 Uiso calc R 1 H N1 0.44813(9) 1.29320(19) 0.52732(10) 0.0477(4) Uani d . 1 N H1A 0.4862 1.3702 0.5519 0.057 Uiso calc R 1 H N2 0.27760(11) 1.2211(2) 0.23497(12) 0.0656(5) Uani d . 1 N O1 0.42765(8) 1.45469(16) 0.39909(8) 0.0525(3) Uani d . 1 O O2 0.40881(11) 0.7845(2) 0.63687(13) 0.0896(6) Uani d . 1 O O3 0.26547(9) 0.85995(17) 0.60199(9) 0.0570(4) Uani d . 1 O O4 0.14408(7) 1.15804(14) 0.39973(8) 0.0461(3) Uani d . 1 O O5 0.01266(8) 0.93290(17) 0.33772(9) 0.0571(4) Uani d . 1 O 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 C1 0.0337(8) 0.0416(10) 0.0515(10) 0.0016(7) 0.0009(7) -0.0033(7) C2 0.0352(8) 0.0389(9) 0.0471(9) 0.0025(7) 0.0007(7) -0.0018(7) C3 0.0353(8) 0.0369(9) 0.0475(9) 0.0036(7) 0.0023(7) -0.0021(7) C4 0.0407(8) 0.0455(10) 0.0476(9) 0.0006(8) -0.0004(7) 0.0012(7) C5 0.0371(8) 0.0499(10) 0.0497(10) 0.0023(8) 0.0005(7) -0.0015(8) C6 0.0411(9) 0.0394(9) 0.0496(10) -0.0029(7) 0.0022(7) 0.0005(7) C7 0.0530(10) 0.0551(11) 0.0489(10) -0.0004(9) -0.0057(8) 0.0055(8) C8 0.0975(18) 0.0661(14) 0.0700(14) -0.0113(13) 0.0170(12) 0.0216(11) C9 0.1015(19) 0.0786(18) 0.0890(18) -0.0343(15) 0.0305(15) 0.0021(13) C10 0.0518(11) 0.0794(15) 0.0523(11) -0.0077(10) -0.0065(9) -0.0041(10) C11 0.0442(9) 0.0362(9) 0.0390(8) -0.0020(7) 0.0016(7) -0.0003(6) C12 0.0442(9) 0.0322(8) 0.0365(8) -0.0023(7) 0.0006(7) 0.0000(6) C13 0.0448(9) 0.0448(10) 0.0410(9) -0.0053(8) 0.0005(7) -0.0010(7) C14 0.0629(12) 0.0437(11) 0.0563(11) -0.0152(9) 0.0036(9) -0.0104(8) C15 0.0705(12) 0.0350(10) 0.0718(13) 0.0013(9) 0.0080(10) -0.0099(9) C16 0.0518(10) 0.0399(10) 0.0639(12) 0.0060(8) 0.0057(9) -0.0036(8) C17 0.0818(15) 0.0545(13) 0.0757(14) 0.0071(11) 0.0214(11) -0.0120(10) C18 0.0517(11) 0.0715(15) 0.0681(13) -0.0222(10) -0.0058(9) -0.0032(10) N1 0.0385(7) 0.0473(9) 0.0532(9) -0.0067(6) -0.0029(6) -0.0051(7) N2 0.0654(10) 0.0727(12) 0.0546(10) -0.0046(9) -0.0010(8) 0.0033(8) O1 0.0480(7) 0.0434(7) 0.0619(8) -0.0079(6) -0.0017(6) 0.0047(6) O2 0.0730(10) 0.0874(12) 0.0991(12) 0.0109(9) -0.0103(9) 0.0411(10) O3 0.0605(8) 0.0515(8) 0.0581(8) -0.0057(6) 0.0082(6) 0.0114(6) O4 0.0456(6) 0.0347(7) 0.0553(7) 0.0011(5) 0.0016(5) 0.0005(5) O5 0.0409(6) 0.0525(8) 0.0718(9) -0.0097(6) -0.0072(6) -0.0029(6) 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' N N 0.0061 0.0033 '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_publ_flag O1 C1 N1 120.73(14) ? O1 C1 C2 124.92(15) ? N1 C1 C2 114.33(15) y C3 C2 C6 121.57(14) ? C3 C2 C1 121.70(15) y C6 C2 C1 116.73(15) ? C2 C3 C4 119.42(14) y C2 C3 C11 120.11(14) ? C4 C3 C11 120.46(14) ? C5 C4 C3 119.53(16) y C5 C4 C7 119.07(15) ? C3 C4 C7 121.39(15) ? N1 C5 C4 118.67(15) y N1 C5 C10 115.76(15) ? C4 C5 C10 125.54(16) ? N2 C6 C2 178.00(18) ? O2 C7 O3 124.17(19) ? O2 C7 C4 123.41(18) ? O3 C7 C4 112.41(15) ? O3 C8 C9 107.19(19) ? O3 C8 H8A 110.3 ? C9 C8 H8A 110.3 ? O3 C8 H8B 110.3 ? C9 C8 H8B 110.3 ? H8A C8 H8B 108.5 ? C8 C9 H9A 109.5 ? C8 C9 H9B 109.5 ? H9A C9 H9B 109.5 ? C8 C9 H9C 109.5 ? H9A C9 H9C 109.5 ? H9B C9 H9C 109.5 ? C5 C10 H10A 109.5 ? C5 C10 H10B 109.5 ? H10A C10 H10B 109.5 ? C5 C10 H10C 109.5 ? H10A C10 H10C 109.5 ? H10B C10 H10C 109.5 ? C12 C11 C16 119.65(15) ? C12 C11 C3 119.47(14) ? C16 C11 C3 120.84(15) ? O4 C12 C11 120.10(13) ? O4 C12 C13 119.65(14) ? C11 C12 C13 120.25(15) ? O5 C13 C14 124.99(15) ? O5 C13 C12 115.60(15) ? C14 C13 C12 119.41(16) ? C13 C14 C15 120.02(17) ? C13 C14 H14A 120.0 ? C15 C14 H14A 120.0 ? C16 C15 C14 121.00(18) ? C16 C15 H15A 119.5 ? C14 C15 H15A 119.5 ? C15 C16 C11 119.68(17) ? C15 C16 H16A 120.2 ? C11 C16 H16A 120.2 ? O4 C17 H17A 109.5 ? O4 C17 H17B 109.5 ? H17A C17 H17B 109.5 ? O4 C17 H17C 109.5 ? H17A C17 H17C 109.5 ? H17B C17 H17C 109.5 ? O5 C18 H18A 109.5 ? O5 C18 H18B 109.5 ? H18A C18 H18B 109.5 ? O5 C18 H18C 109.5 ? H18A C18 H18C 109.5 ? H18B C18 H18C 109.5 ? C5 N1 C1 126.15(14) y C5 N1 H1A 116.9 ? C1 N1 H1A 116.9 ? C7 O3 C8 116.59(16) ? C12 O4 C17 113.89(14) ? C13 O5 C18 117.53(14) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 O1 1.236(2) ? C1 N1 1.374(2) y C1 C2 1.435(2) y C2 C3 1.376(2) y C2 C6 1.431(2) ? C3 C4 1.419(2) y C3 C11 1.492(2) ? C4 C5 1.376(2) y C4 C7 1.493(3) ? C5 N1 1.356(2) y C5 C10 1.497(2) ? C6 N2 1.144(2) ? C7 O2 1.196(2) ? C7 O3 1.321(2) ? C8 O3 1.456(2) ? C8 C9 1.488(3) ? C8 H8A 0.9700 ? C8 H8B 0.9700 ? C9 H9A 0.9600 ? C9 H9B 0.9600 ? C9 H9C 0.9600 ? C10 H10A 0.9600 ? C10 H10B 0.9600 ? C10 H10C 0.9600 ? C11 C12 1.385(2) ? C11 C16 1.394(2) ? C12 O4 1.3761(19) ? C12 C13 1.401(2) ? C13 O5 1.363(2) ? C13 C14 1.379(3) ? C14 C15 1.384(3) ? C14 H14A 0.9300 ? C15 C16 1.373(3) ? C15 H15A 0.9300 ? C16 H16A 0.9300 ? C17 O4 1.418(2) ? C17 H17A 0.9600 ? C17 H17B 0.9600 ? C17 H17C 0.9600 ? C18 O5 1.422(2) ? C18 H18A 0.9600 ? C18 H18B 0.9600 ? C18 H18C 0.9600 ? N1 H1A 0.8600 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C16 H16A O1 1_545 0.93 2.48 3.2630(10) 141 N1 H1A O1 3_686 0.86 1.92 2.780(2) 177 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 _geom_torsion_publ_flag O1 C1 C2 C3 -174.95(16) ? N1 C1 C2 C3 3.4(2) y O1 C1 C2 C6 5.2(2) ? N1 C1 C2 C6 -176.37(14) ? C6 C2 C3 C4 174.61(15) ? C1 C2 C3 C4 -5.2(2) y C6 C2 C3 C11 -4.2(2) ? C1 C2 C3 C11 175.96(14) ? C2 C3 C4 C5 2.8(2) y C11 C3 C4 C5 -178.31(15) ? C2 C3 C4 C7 -175.82(16) ? C11 C3 C4 C7 3.0(2) ? C3 C4 C5 N1 1.1(2) y C7 C4 C5 N1 179.75(16) ? C3 C4 C5 C10 179.17(16) ? C7 C4 C5 C10 -2.1(3) ? C5 C4 C7 O2 -51.8(3) ? C3 C4 C7 O2 126.9(2) ? C5 C4 C7 O3 128.92(17) ? C3 C4 C7 O3 -52.4(2) yes C2 C3 C11 C12 -65.9(2) yes C4 C3 C11 C12 115.23(17) ? C2 C3 C11 C16 116.45(18) ? C4 C3 C11 C16 -62.4(2) ? C16 C11 C12 O4 -179.13(15) ? C3 C11 C12 O4 3.2(2) ? C16 C11 C12 C13 0.7(2) ? C3 C11 C12 C13 -176.97(14) ? O4 C12 C13 O5 -0.6(2) ? C11 C12 C13 O5 179.60(14) ? O4 C12 C13 C14 179.18(15) ? C11 C12 C13 C14 -0.6(2) ? O5 C13 C14 C15 179.99(17) ? C12 C13 C14 C15 0.2(3) ? C13 C14 C15 C16 0.1(3) ? C14 C15 C16 C11 0.0(3) ? C12 C11 C16 C15 -0.3(3) ? C3 C11 C16 C15 177.27(17) ? C4 C5 N1 C1 -2.9(3) y C10 C5 N1 C1 178.79(16) ? O1 C1 N1 C5 179.16(16) ? C2 C1 N1 C5 0.7(2) y O2 C7 O3 C8 -7.7(3) ? C4 C7 O3 C8 171.60(17) ? C9 C8 O3 C7 -165.37(19) ? C11 C12 O4 C17 -95.16(18) ? C13 C12 O4 C17 85.03(19) ? C14 C13 O5 C18 0.3(3) ? C12 C13 O5 C18 -179.93(15) ?