#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/68/2206847.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_2206847 loop_ _publ_author_name 'Yu, Chen-Xia' 'Shi, Da-Qing' 'Yao, Chang-Sheng' 'Wang, Xiang-Shan' 'Zhuang, Qi-Ya' _publ_section_title ; Methyl 2-methyl-5-oxo-4-p-tolyl-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate ; _journal_coeditor_code BH6021 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3224 _journal_page_last o3225 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C19 H21 N O3' _chemical_formula_moiety 'C19 H21 N O3' _chemical_formula_sum 'C19 H21 N O3' _chemical_formula_weight 311.37 _chemical_name_systematic ; Methyl 2-methyl-5-oxo-4-p-tolyl-1,4,5,6,7,8-hexahydroquinoline-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 105.436(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.8338(15) _cell_length_b 15.095(3) _cell_length_c 13.962(3) _cell_measurement_reflns_used 7332 _cell_measurement_temperature 193(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3.0 _cell_volume 1591.5(6) _computing_cell_refinement CrystalClear _computing_data_collection 'CrystalClear (Rigaku, 1999)' _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _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 193(2) _diffrn_detector_area_resol_mean 7.31 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71070 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 17357 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 3.02 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 0.9784 _exptl_absorpt_correction_T_min 0.9388 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Jacobson, 1998)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.73 _exptl_crystal_size_mid 0.62 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.249 _refine_diff_density_min -0.238 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 216 _refine_ls_number_reflns 3637 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0456 _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^)+(0.0636P)^2^+0.5891P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1209 _refine_ls_wR_factor_ref 0.1239 _reflns_number_gt 3378 _reflns_number_total 3637 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bh6021.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_original_cell_volume 1591.5(5) _cod_database_code 2206847 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_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_ _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 O1 0.39522(14) 0.21452(7) 0.09977(7) 0.0346(2) Uani d . 1 O O2 0.96668(14) 0.41203(9) 0.41562(8) 0.0441(3) Uani d . 1 O O3 0.86076(12) 0.42985(7) 0.25115(7) 0.0309(2) Uani d . 1 O N1 0.43779(14) 0.33862(7) 0.41278(8) 0.0251(2) Uani d . 1 N C1 0.35039(16) 0.28794(8) 0.33350(9) 0.0220(2) Uani d . 1 C C2 0.40187(15) 0.28928(8) 0.24778(8) 0.0210(2) Uani d . 1 C C3 0.53959(15) 0.35590(8) 0.23502(8) 0.0221(3) Uani d . 1 C H3 0.6117 0.3276 0.1941 0.027 Uiso calc R 1 H C4 0.66256(16) 0.37812(8) 0.33611(9) 0.0230(3) Uani d . 1 C C5 0.60375(16) 0.37424(8) 0.41910(9) 0.0238(3) Uani d . 1 C C6 0.33129(16) 0.22424(8) 0.17099(9) 0.0244(3) Uani d . 1 C C7 0.18101(18) 0.16599(9) 0.18145(11) 0.0319(3) Uani d . 1 C H7A 0.2293 0.1081 0.2093 0.038 Uiso calc R 1 H H7B 0.1000 0.1552 0.1148 0.038 Uiso calc R 1 H C8 0.07639(18) 0.20670(9) 0.24836(10) 0.0309(3) Uani d . 1 C H8A 0.0133 0.2603 0.2164 0.037 Uiso calc R 1 H H8B -0.0128 0.1638 0.2585 0.037 Uiso calc R 1 H C9 0.20191(18) 0.23118(9) 0.34801(10) 0.0294(3) Uani d . 1 C H9A 0.1361 0.2636 0.3885 0.035 Uiso calc R 1 H H9B 0.2511 0.1766 0.3843 0.035 Uiso calc R 1 H C10 0.44748(16) 0.43728(8) 0.17868(9) 0.0240(3) Uani d . 1 C C11 0.3751(3) 0.43195(11) 0.07656(11) 0.0461(4) Uani d . 1 C H11 0.3873 0.3787 0.0427 0.055 Uiso calc R 1 H C12 0.2854(3) 0.50304(12) 0.02328(12) 0.0546(5) Uani d . 1 C H12 0.2369 0.4974 -0.0464 0.065 Uiso calc R 1 H C13 0.2648(2) 0.58212(10) 0.06909(11) 0.0367(3) Uani d . 1 C C14 0.33865(18) 0.58778(9) 0.17087(10) 0.0303(3) Uani d . 1 C H14 0.3277 0.6414 0.2044 0.036 Uiso calc R 1 H C15 0.42844(16) 0.51653(9) 0.22486(9) 0.0266(3) Uani d . 1 C H15 0.4775 0.5223 0.2945 0.032 Uiso calc R 1 H C16 0.84361(17) 0.40792(9) 0.34183(9) 0.0258(3) Uani d . 1 C C17 1.03324(17) 0.46132(10) 0.24855(11) 0.0332(3) Uani d . 1 C H17A 1.0679 0.5111 0.2947 0.050 Uiso calc R 1 H H17B 1.0292 0.4809 0.1811 0.050 Uiso calc R 1 H H17C 1.1198 0.4133 0.2681 0.050 Uiso calc R 1 H C18 0.69805(19) 0.40596(10) 0.52161(10) 0.0333(3) Uani d . 1 C H18A 0.7600 0.3562 0.5609 0.050 Uiso calc R 1 H H18B 0.6117 0.4306 0.5538 0.050 Uiso calc R 1 H H18C 0.7840 0.4518 0.5169 0.050 Uiso calc R 1 H C19 0.1671(3) 0.65923(12) 0.00988(14) 0.0545(5) Uani d . 1 C H19A 0.1741 0.7107 0.0536 0.082 Uiso calc R 1 H H19B 0.0427 0.6431 -0.0184 0.082 Uiso calc R 1 H H19C 0.2212 0.6739 -0.0439 0.082 Uiso calc R 1 H H1 0.404(2) 0.3317(12) 0.4656(13) 0.036(4) Uiso d . 1 H 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 O1 0.0417(6) 0.0396(6) 0.0250(5) -0.0066(4) 0.0132(4) -0.0112(4) O2 0.0264(5) 0.0687(8) 0.0327(6) -0.0094(5) -0.0001(4) 0.0002(5) O3 0.0225(4) 0.0420(6) 0.0297(5) -0.0061(4) 0.0096(4) -0.0002(4) N1 0.0271(5) 0.0338(6) 0.0162(5) -0.0025(4) 0.0088(4) -0.0009(4) C1 0.0220(5) 0.0234(6) 0.0204(5) 0.0018(4) 0.0052(4) 0.0019(4) C2 0.0200(5) 0.0234(6) 0.0197(5) -0.0001(4) 0.0053(4) 0.0002(4) C3 0.0225(6) 0.0271(6) 0.0179(5) -0.0031(5) 0.0072(4) -0.0024(4) C4 0.0216(6) 0.0260(6) 0.0208(6) -0.0009(5) 0.0048(4) -0.0018(4) C5 0.0242(6) 0.0264(6) 0.0198(6) 0.0012(5) 0.0041(4) -0.0011(4) C6 0.0260(6) 0.0249(6) 0.0216(6) 0.0008(5) 0.0052(5) -0.0013(4) C7 0.0308(7) 0.0294(7) 0.0344(7) -0.0070(5) 0.0068(5) -0.0066(5) C8 0.0258(6) 0.0313(7) 0.0360(7) -0.0062(5) 0.0089(5) -0.0009(5) C9 0.0302(6) 0.0329(7) 0.0276(6) -0.0050(5) 0.0120(5) 0.0030(5) C10 0.0248(6) 0.0281(6) 0.0195(6) -0.0060(5) 0.0064(5) 0.0009(4) C11 0.0779(12) 0.0317(8) 0.0219(7) 0.0030(8) 0.0013(7) -0.0022(6) C12 0.0893(14) 0.0386(9) 0.0232(7) 0.0040(9) -0.0070(8) 0.0028(6) C13 0.0424(8) 0.0316(7) 0.0323(7) -0.0039(6) 0.0034(6) 0.0079(6) C14 0.0280(6) 0.0288(7) 0.0342(7) -0.0044(5) 0.0084(5) -0.0016(5) C15 0.0247(6) 0.0323(7) 0.0228(6) -0.0041(5) 0.0064(5) -0.0028(5) C16 0.0238(6) 0.0274(6) 0.0261(6) -0.0006(5) 0.0063(5) -0.0034(5) C17 0.0244(6) 0.0352(7) 0.0428(8) -0.0043(5) 0.0141(6) 0.0005(6) C18 0.0339(7) 0.0440(8) 0.0199(6) -0.0041(6) 0.0037(5) -0.0058(5) C19 0.0690(12) 0.0375(9) 0.0482(10) 0.0043(8) 0.0000(9) 0.0112(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C6 1.2354(16) yes O2 C16 1.2108(16) yes O3 C16 1.3495(16) yes O3 C17 1.4418(15) yes N1 C1 1.3696(16) yes N1 C5 1.3878(16) yes N1 H1 0.854(18) ? C1 C2 1.3610(16) ? C1 C9 1.5012(17) ? C2 C6 1.4503(17) ? C2 C3 1.5196(16) ? C3 C4 1.5195(16) ? C3 C10 1.5318(17) ? C3 H3 1.0000 ? C4 C5 1.3573(17) ? C4 C16 1.4697(17) ? C5 C18 1.5035(17) ? C6 C7 1.5074(18) ? C7 C8 1.526(2) ? C7 H7A 0.9900 ? C7 H7B 0.9900 ? C8 C9 1.5201(19) ? C8 H8A 0.9900 ? C8 H8B 0.9900 ? C9 H9A 0.9900 ? C9 H9B 0.9900 ? C10 C15 1.3858(18) ? C10 C11 1.3893(19) ? C11 C12 1.386(2) ? C11 H11 0.9500 ? C12 C13 1.384(2) ? C12 H12 0.9500 ? C13 C14 1.387(2) ? C13 C19 1.512(2) ? C14 C15 1.3920(19) ? C14 H14 0.9500 ? C15 H15 0.9500 ? C17 H17A 0.9800 ? C17 H17B 0.9800 ? C17 H17C 0.9800 ? C18 H18A 0.9800 ? C18 H18B 0.9800 ? C18 H18C 0.9800 ? C19 H19A 0.9800 ? C19 H19B 0.9800 ? C19 H19C 0.9800 ? 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 C16 O3 C17 115.62(10) yes C1 N1 C5 121.74(10) yes C1 N1 H1 115.3(12) ? C5 N1 H1 119.6(11) ? C2 C1 N1 120.07(11) ? C2 C1 C9 123.28(11) ? N1 C1 C9 116.64(10) ? C1 C2 C6 119.74(11) ? C1 C2 C3 119.91(10) ? C6 C2 C3 120.28(10) ? C4 C3 C2 109.36(9) ? C4 C3 C10 113.30(10) ? C2 C3 C10 109.80(10) ? C4 C3 H3 108.1 ? C2 C3 H3 108.1 ? C10 C3 H3 108.1 ? C5 C4 C16 120.58(11) ? C5 C4 C3 120.53(11) ? C16 C4 C3 118.82(10) ? C4 C5 N1 119.18(11) ? C4 C5 C18 127.33(12) ? N1 C5 C18 113.49(11) ? O1 C6 C2 121.26(11) ? O1 C6 C7 120.20(11) ? C2 C6 C7 118.51(11) ? C6 C7 C8 112.63(11) ? C6 C7 H7A 109.1 ? C8 C7 H7A 109.1 ? C6 C7 H7B 109.1 ? C8 C7 H7B 109.1 ? H7A C7 H7B 107.8 ? C9 C8 C7 109.64(11) ? C9 C8 H8A 109.7 ? C7 C8 H8A 109.7 ? C9 C8 H8B 109.7 ? C7 C8 H8B 109.7 ? H8A C8 H8B 108.2 ? C1 C9 C8 110.55(10) ? C1 C9 H9A 109.5 ? C8 C9 H9A 109.5 ? C1 C9 H9B 109.5 ? C8 C9 H9B 109.5 ? H9A C9 H9B 108.1 ? C15 C10 C11 117.55(12) ? C15 C10 C3 123.21(11) ? C11 C10 C3 119.23(12) ? C12 C11 C10 121.07(15) ? C12 C11 H11 119.5 ? C10 C11 H11 119.5 ? C13 C12 C11 121.65(14) ? C13 C12 H12 119.2 ? C11 C12 H12 119.2 ? C12 C13 C14 117.29(13) ? C12 C13 C19 121.04(14) ? C14 C13 C19 121.67(15) ? C13 C14 C15 121.34(13) ? C13 C14 H14 119.3 ? C15 C14 H14 119.3 ? C10 C15 C14 121.10(12) ? C10 C15 H15 119.5 ? C14 C15 H15 119.5 ? O2 C16 O3 122.02(12) ? O2 C16 C4 126.88(12) ? O3 C16 C4 111.09(10) ? O3 C17 H17A 109.5 ? O3 C17 H17B 109.5 ? H17A C17 H17B 109.5 ? O3 C17 H17C 109.5 ? H17A C17 H17C 109.5 ? H17B C17 H17C 109.5 ? C5 C18 H18A 109.5 ? C5 C18 H18B 109.5 ? H18A C18 H18B 109.5 ? C5 C18 H18C 109.5 ? H18A C18 H18C 109.5 ? H18B C18 H18C 109.5 ? C13 C19 H19A 109.5 ? C13 C19 H19B 109.5 ? H19A C19 H19B 109.5 ? C13 C19 H19C 109.5 ? H19A C19 H19C 109.5 ? H19B C19 H19C 109.5 ? 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 C5 N1 C1 C2 -16.61(18) C5 N1 C1 C9 162.02(11) N1 C1 C2 C6 168.83(11) C9 C1 C2 C6 -9.71(18) N1 C1 C2 C3 -8.18(17) C9 C1 C2 C3 173.28(11) C1 C2 C3 C4 28.90(15) C6 C2 C3 C4 -148.09(11) C1 C2 C3 C10 -95.99(13) C6 C2 C3 C10 87.01(13) C2 C3 C4 C5 -29.11(16) C10 C3 C4 C5 93.73(14) C2 C3 C4 C16 153.75(11) C10 C3 C4 C16 -83.41(14) C16 C4 C5 N1 -174.45(11) C3 C4 C5 N1 8.46(18) C16 C4 C5 C18 6.4(2) C3 C4 C5 C18 -170.67(13) C1 N1 C5 C4 16.47(18) C1 N1 C5 C18 -164.29(12) C1 C2 C6 O1 -168.41(12) C3 C2 C6 O1 8.59(18) C1 C2 C6 C7 9.54(18) C3 C2 C6 C7 -173.46(11) O1 C6 C7 C8 -159.19(12) C2 C6 C7 C8 22.84(17) C6 C7 C8 C9 -53.74(15) C2 C1 C9 C8 -22.58(17) N1 C1 C9 C8 158.83(11) C7 C8 C9 C1 52.88(15) C4 C3 C10 C15 -20.61(16) C2 C3 C10 C15 101.99(13) C4 C3 C10 C11 160.92(13) C2 C3 C10 C11 -76.49(16) C15 C10 C11 C12 -0.8(3) C3 C10 C11 C12 177.79(16) C10 C11 C12 C13 0.3(3) C11 C12 C13 C14 0.4(3) C11 C12 C13 C19 179.79(19) C12 C13 C14 C15 -0.6(2) C19 C13 C14 C15 -179.97(15) C11 C10 C15 C14 0.6(2) C3 C10 C15 C14 -177.92(11) C13 C14 C15 C10 0.1(2) C17 O3 C16 O2 -2.07(19) C17 O3 C16 C4 179.13(11) C5 C4 C16 O2 17.9(2) C3 C4 C16 O2 -164.94(14) C5 C4 C16 O3 -163.35(12) C3 C4 C16 O3 13.79(16) 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 _geom_hbond_publ_flag N1 H1 O1 4_566 0.854(18) 2.017(18) 2.8343(15) 159.9(16) yes _cod_database_fobs_code 2206847