#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/25/2202598.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_2202598 loop_ _publ_author_name 'Xue-Mei Li' 'Lei Wang' 'Jian-Hua Xu' 'Shu-Sheng Zhang' 'Hoong-Kun Fun' _publ_section_title ; Ethyl 2-(acetylamino)-2-(9-hydroxy-10-oxo-9,10-dihydro-9-phenanthrenyl)acetate ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1907 _journal_page_last o1908 _journal_paper_doi 10.1107/S1600536803024590 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C20 H19 N O5' _chemical_formula_moiety 'C20 H19 N O5' _chemical_formula_sum 'C20 H19 N O5' _chemical_formula_weight 353.36 _chemical_melting_point 436.1(10) _chemical_name_systematic ;Ethyl 2-(acetylamino)-2-(9-hydroxy-10-oxo-9,10-dihydro-9-phenanthrenyl)acetate ; _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 82.7950(10) _cell_angle_beta 80.2410(10) _cell_angle_gamma 64.4150(10) _cell_formula_units_Z 2 _cell_length_a 7.7205(5) _cell_length_b 8.8797(6) _cell_length_c 14.1801(10) _cell_measurement_reflns_used 3047 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.26 _cell_measurement_theta_min 2.55 _cell_volume 862.63(10) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method \w _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 0.0113 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 4335 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.55 _diffrn_standards_decay_% negligible _diffrn_standards_interval_count none _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_T_max 0.9825 _exptl_absorpt_correction_T_min 0.9543 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 372 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.293 _refine_diff_density_min -0.189 _refine_ls_extinction_coef none _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 248 _refine_ls_number_reflns 2990 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.078 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0421 _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^)+(0.0553P)^2^+0.2776P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1096 _refine_ls_wR_factor_ref 0.1168 _reflns_number_gt 2553 _reflns_number_total 2990 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cv6250.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 '162-164\%' was changed to '436.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K), 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 '162-164\%' was changed to '436.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K), the average value was taken and precision was estimated. '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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_database_code 2202598 _cod_database_fobs_code 2202598 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.68509(19) 0.03669(17) 0.13722(9) 0.0430(3) Uani d . 1 . . O O2 0.6399(2) -0.10534(18) 0.31295(10) 0.0559(4) Uani d . 1 . . O O3 1.10098(19) -0.23422(17) 0.08638(9) 0.0506(4) Uani d . 1 . . O O4 1.05710(18) -0.27846(15) 0.24610(9) 0.0458(3) Uani d . 1 . . O O5 1.2970(2) 0.0683(2) 0.17956(10) 0.0672(5) Uani d . 1 . . O N1 1.0457(2) 0.09081(19) 0.11072(10) 0.0362(3) Uani d . 1 . . N H2A 0.995(3) 0.117(2) 0.0649(15) 0.046(6) Uiso d . 1 . . H C1 0.6804(2) 0.2663(2) 0.21683(12) 0.0356(4) Uani d . 1 . . C C2 0.6261(3) 0.3703(2) 0.13518(13) 0.0444(4) Uani d . 1 . . C H2 0.6297 0.3247 0.0789 0.053 Uiso calc R 1 . . H C3 0.5665(3) 0.5410(3) 0.13691(15) 0.0538(5) Uani d . 1 . . C H3 0.5285 0.6098 0.0822 0.065 Uiso calc R 1 . . H C4 0.5635(3) 0.6091(3) 0.21974(17) 0.0572(5) Uani d . 1 . . C H4 0.5257 0.7236 0.2207 0.069 Uiso calc R 1 . . H C5 0.6167(3) 0.5071(2) 0.30100(15) 0.0509(5) Uani d . 1 . . C H5 0.6137 0.5541 0.3566 0.061 Uiso calc R 1 . . H C6 0.6751(2) 0.3343(2) 0.30192(12) 0.0380(4) Uani d . 1 . . C C7 0.7175(2) 0.2252(2) 0.39107(12) 0.0401(4) Uani d . 1 . . C C8 0.7401(3) 0.2795(3) 0.47484(14) 0.0531(5) Uani d . 1 . . C H8 0.7392 0.3848 0.4741 0.064 Uiso calc R 1 . . H C9 0.7638(3) 0.1786(3) 0.55865(14) 0.0610(6) Uani d . 1 . . C H9 0.7804 0.2163 0.6133 0.073 Uiso calc R 1 . . H C10 0.7633(3) 0.0233(3) 0.56239(14) 0.0585(6) Uani d . 1 . . C H10 0.7767 -0.0425 0.6195 0.070 Uiso calc R 1 . . H C11 0.7427(3) -0.0338(3) 0.48122(13) 0.0510(5) Uani d . 1 . . C H11 0.7420 -0.1387 0.4833 0.061 Uiso calc R 1 . . H C12 0.7228(2) 0.0656(2) 0.39500(12) 0.0390(4) Uani d . 1 . . C C13 0.6995(2) 0.0010(2) 0.30906(12) 0.0369(4) Uani d . 1 . . C C14 0.7539(2) 0.0774(2) 0.21178(11) 0.0333(4) Uani d . 1 . . C C15 0.9808(2) -0.0016(2) 0.18820(11) 0.0325(4) Uani d . 1 . . C C16 1.0538(2) -0.1834(2) 0.16553(12) 0.0362(4) Uani d . 1 . . C C17 1.0969(3) -0.4524(3) 0.23745(17) 0.0608(6) Uani d . 1 . . C H17A 1.2166 -0.5063 0.1954 0.073 Uiso calc R 1 . . H H17B 0.9928 -0.4589 0.2108 0.073 Uiso calc R 1 . . H C18 1.1133(5) -0.5366(4) 0.3353(2) 0.0935(9) Uani d . 1 . . C H18A 1.1286 -0.6493 0.3328 0.140 Uiso calc R 1 . . H H18B 0.9982 -0.4767 0.3775 0.140 Uiso calc R 1 . . H H18C 1.2237 -0.5380 0.3587 0.140 Uiso calc R 1 . . H C19 1.1999(3) 0.1214(2) 0.11252(12) 0.0402(4) Uani d . 1 . . C C20 1.2471(3) 0.2251(3) 0.02954(14) 0.0538(5) Uani d . 1 . . C H20A 1.3672 0.2293 0.0350 0.081 Uiso calc R 1 . . H H20B 1.1456 0.3364 0.0296 0.081 Uiso calc R 1 . . H H20C 1.2587 0.1763 -0.0292 0.081 Uiso calc R 1 . . H H15 1.034(2) -0.0015(19) 0.2411(12) 0.028(4) Uiso d . 1 . . H H1A 0.574(4) 0.041(3) 0.1590(18) 0.077(8) 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 0.0351(7) 0.0632(8) 0.0372(7) -0.0242(6) -0.0057(5) -0.0118(6) O2 0.0594(9) 0.0673(9) 0.0558(9) -0.0435(8) 0.0028(7) -0.0053(7) O3 0.0500(8) 0.0562(8) 0.0369(7) -0.0127(6) -0.0039(6) -0.0111(6) O4 0.0485(7) 0.0439(7) 0.0413(7) -0.0183(6) -0.0026(6) 0.0019(5) O5 0.0558(9) 0.1136(13) 0.0530(9) -0.0562(9) -0.0238(7) 0.0226(8) N1 0.0322(7) 0.0527(9) 0.0274(8) -0.0217(7) -0.0075(6) 0.0042(6) C1 0.0259(8) 0.0451(10) 0.0342(9) -0.0145(7) -0.0029(6) 0.0003(7) C2 0.0377(10) 0.0555(12) 0.0389(10) -0.0195(9) -0.0063(7) 0.0026(8) C3 0.0452(11) 0.0549(12) 0.0584(13) -0.0223(9) -0.0105(9) 0.0171(10) C4 0.0499(12) 0.0436(11) 0.0780(15) -0.0208(9) -0.0107(10) 0.0043(10) C5 0.0456(11) 0.0491(11) 0.0582(12) -0.0181(9) -0.0068(9) -0.0107(9) C6 0.0290(8) 0.0423(10) 0.0418(9) -0.0139(7) -0.0018(7) -0.0077(7) C7 0.0306(9) 0.0518(11) 0.0333(9) -0.0126(8) -0.0008(7) -0.0091(8) C8 0.0505(11) 0.0624(13) 0.0418(11) -0.0158(10) -0.0061(9) -0.0169(9) C9 0.0496(12) 0.0876(17) 0.0338(10) -0.0139(11) -0.0058(8) -0.0164(10) C10 0.0467(11) 0.0843(16) 0.0300(10) -0.0171(11) -0.0027(8) 0.0059(10) C11 0.0410(10) 0.0648(13) 0.0410(10) -0.0202(9) -0.0007(8) 0.0049(9) C12 0.0299(8) 0.0535(11) 0.0299(9) -0.0155(8) 0.0012(6) -0.0035(7) C13 0.0275(8) 0.0418(9) 0.0402(9) -0.0151(7) 0.0012(7) -0.0033(7) C14 0.0280(8) 0.0462(10) 0.0289(8) -0.0172(7) -0.0046(6) -0.0061(7) C15 0.0293(8) 0.0464(10) 0.0243(8) -0.0178(7) -0.0053(6) -0.0008(7) C16 0.0261(8) 0.0483(10) 0.0327(9) -0.0136(7) -0.0055(6) -0.0023(7) C17 0.0543(12) 0.0456(11) 0.0811(16) -0.0227(10) -0.0016(11) -0.0015(10) C18 0.107(2) 0.0690(17) 0.112(2) -0.0477(17) -0.0316(18) 0.0341(16) C19 0.0385(9) 0.0519(11) 0.0354(9) -0.0240(8) -0.0052(7) -0.0019(8) C20 0.0641(13) 0.0691(13) 0.0453(11) -0.0457(11) -0.0072(9) 0.0035(9) 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 C14 O1 H1A 106.9(17) ? C16 O4 C17 117.47(15) ? C19 N1 C15 121.97(14) ? C19 N1 H2A 118.8(15) ? C15 N1 H2A 119.0(15) ? C2 C1 C6 120.02(17) ? C2 C1 C14 119.45(15) ? C6 C1 C14 120.48(15) ? C3 C2 C1 120.54(18) ? C3 C2 H2 119.7 ? C1 C2 H2 119.7 ? C4 C3 C2 120.02(18) ? C4 C3 H3 120.0 ? C2 C3 H3 120.0 ? C5 C4 C3 119.81(19) ? C5 C4 H4 120.1 ? C3 C4 H4 120.1 ? C4 C5 C6 121.54(19) ? C4 C5 H5 119.2 ? C6 C5 H5 119.2 ? C5 C6 C1 118.06(17) ? C5 C6 C7 121.89(16) ? C1 C6 C7 119.91(15) ? C12 C7 C8 117.66(17) ? C12 C7 C6 119.51(15) ? C8 C7 C6 122.69(18) ? C9 C8 C7 120.8(2) ? C9 C8 H8 119.6 ? C7 C8 H8 119.6 ? C10 C9 C8 121.01(19) ? C10 C9 H9 119.5 ? C8 C9 H9 119.5 ? C11 C10 C9 119.50(19) ? C11 C10 H10 120.2 ? C9 C10 H10 120.2 ? C10 C11 C12 120.2(2) ? C10 C11 H11 119.9 ? C12 C11 H11 119.9 ? C7 C12 C11 120.77(17) ? C7 C12 C13 120.28(15) ? C11 C12 C13 118.90(17) ? O2 C13 C12 123.19(16) ? O2 C13 C14 120.32(16) ? C12 C13 C14 116.49(14) ? O1 C14 C1 112.05(13) yes O1 C14 C13 111.47(13) yes C1 C14 C13 109.74(13) yes O1 C14 C15 106.05(13) yes C1 C14 C15 108.84(12) yes C13 C14 C15 108.54(13) yes N1 C15 C16 110.91(13) ? N1 C15 C14 111.97(13) ? C16 C15 C14 109.64(13) ? N1 C15 H15 107.9(10) ? C16 C15 H15 106.7(10) ? C14 C15 H15 109.5(10) ? O3 C16 O4 124.74(17) ? O3 C16 C15 125.09(15) ? O4 C16 C15 110.18(14) ? O4 C17 C18 107.5(2) ? O4 C17 H17A 110.2 ? C18 C17 H17A 110.2 ? O4 C17 H17B 110.2 ? C18 C17 H17B 110.2 ? H17A C17 H17B 108.5 ? C17 C18 H18A 109.5 ? C17 C18 H18B 109.5 ? H18A C18 H18B 109.5 ? C17 C18 H18C 109.5 ? H18A C18 H18C 109.5 ? H18B C18 H18C 109.5 ? O5 C19 N1 121.59(16) ? O5 C19 C20 121.71(16) ? N1 C19 C20 116.69(15) ? C19 C20 H20A 109.5 ? C19 C20 H20B 109.5 ? H20A C20 H20B 109.5 ? C19 C20 H20C 109.5 ? H20A C20 H20C 109.5 ? H20B C20 H20C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C14 . 1.4080(19) yes O1 H1A . 0.85(3) ? O2 C13 . 1.209(2) yes O3 C16 . 1.201(2) ? O4 C16 . 1.330(2) ? O4 C17 . 1.456(2) ? O5 C19 . 1.230(2) ? N1 C19 . 1.335(2) ? N1 C15 . 1.440(2) ? N1 H2A . 0.77(2) ? C1 C2 . 1.389(2) ? C1 C6 . 1.402(2) ? C1 C14 . 1.529(2) yes C2 C3 . 1.383(3) ? C2 H2 . 0.9300 ? C3 C4 . 1.379(3) ? C3 H3 . 0.9300 ? C4 C5 . 1.376(3) ? C4 H4 . 0.9300 ? C5 C6 . 1.399(3) ? C5 H5 . 0.9300 ? C6 C7 . 1.484(2) ? C7 C12 . 1.395(3) ? C7 C8 . 1.400(3) ? C8 C9 . 1.384(3) ? C8 H8 . 0.9300 ? C9 C10 . 1.375(3) ? C9 H9 . 0.9300 ? C10 C11 . 1.373(3) ? C10 H10 . 0.9300 ? C11 C12 . 1.405(3) ? C11 H11 . 0.9300 ? C12 C13 . 1.478(2) ? C13 C14 . 1.534(2) yes C14 C15 . 1.572(2) yes C15 C16 . 1.520(2) ? C15 H15 . 0.916(17) ? C17 C18 . 1.490(4) ? C17 H17A . 0.9700 ? C17 H17B . 0.9700 ? C18 H18A . 0.9600 ? C18 H18B . 0.9600 ? C18 H18C . 0.9600 ? C19 C20 . 1.496(2) ? C20 H20A . 0.9600 ? C20 H20B . 0.9600 ? C20 H20C . 0.9600 ? 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 O1 H1A O5 1_455 0.85(3) 2.02(3) 2.850(2) 167(2) yes N1 H2A O3 2_755 0.77(2) 2.36(2) 3.106(2) 164(2) yes C20 H20C O1 2_755 0.96 2.43 3.343(3) 159 yes 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 C6 C1 C2 C3 0.1(3) C14 C1 C2 C3 -177.39(15) C1 C2 C3 C4 1.0(3) C2 C3 C4 C5 -1.1(3) C3 C4 C5 C6 0.3(3) C4 C5 C6 C1 0.7(3) C4 C5 C6 C7 -175.00(17) C2 C1 C6 C5 -0.9(2) C14 C1 C6 C5 176.52(15) C2 C1 C6 C7 174.93(15) C14 C1 C6 C7 -7.6(2) C5 C6 C7 C12 162.48(16) C1 C6 C7 C12 -13.2(2) C5 C6 C7 C8 -13.1(3) C1 C6 C7 C8 171.21(16) C12 C7 C8 C9 -1.0(3) C6 C7 C8 C9 174.70(17) C7 C8 C9 C10 -0.9(3) C8 C9 C10 C11 1.3(3) C9 C10 C11 C12 0.1(3) C8 C7 C12 C11 2.4(2) C6 C7 C12 C11 -173.42(15) C8 C7 C12 C13 179.90(16) C6 C7 C12 C13 4.1(2) C10 C11 C12 C7 -2.0(3) C10 C11 C12 C13 -179.55(16) C7 C12 C13 O2 -154.82(18) C11 C12 C13 O2 22.7(3) C7 C12 C13 C14 24.7(2) C11 C12 C13 C14 -157.76(15) C2 C1 C14 O1 -24.4(2) C6 C1 C14 O1 158.16(14) C2 C1 C14 C13 -148.80(15) C6 C1 C14 C13 33.76(19) C2 C1 C14 C15 92.55(17) C6 C1 C14 C15 -84.88(17) O2 C13 C14 O1 13.2(2) C12 C13 C14 O1 -166.31(14) O2 C13 C14 C1 137.96(16) C12 C13 C14 C1 -41.58(18) O2 C13 C14 C15 -103.22(18) C12 C13 C14 C15 77.25(17) C19 N1 C15 C16 -98.40(18) C19 N1 C15 C14 138.77(16) O1 C14 C15 N1 74.20(17) C1 C14 C15 N1 -46.52(17) C13 C14 C15 N1 -165.92(13) O1 C14 C15 C16 -49.35(16) C1 C14 C15 C16 -170.07(12) C13 C14 C15 C16 70.53(16) C17 O4 C16 O3 -8.3(2) C17 O4 C16 C15 171.44(14) N1 C15 C16 O3 -23.2(2) C14 C15 C16 O3 100.97(18) N1 C15 C16 O4 157.11(13) C14 C15 C16 O4 -78.72(16) C16 O4 C17 C18 174.21(18) C15 N1 C19 O5 1.9(3) C15 N1 C19 C20 -177.39(16) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139066122