#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/66/2206655.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_2206655 loop_ _publ_author_name 'Xian-Wen Li' 'Feng Zhi' 'Jian-Hua Shen' 'Yi-Qiao Hu' _publ_section_title ;1-Cyclopropyl-6-fluoro-7-(4-formylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid. Corrigendum ; _journal_coeditor_code CI6625 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first e3 _journal_page_last e3 _journal_paper_doi 10.1107/S1600536805024426 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C18 H18 F N3 O4' _chemical_formula_moiety 'C18 H18 F N3 O4' _chemical_formula_sum 'C18 H18 F N3 O4' _chemical_formula_weight 359.35 _chemical_name_systematic ;1-Cyclopropyl-6-fluoro-7-(4-formylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3- carboxylic acid ; _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 102.57(3) _cell_angle_beta 96.58(3) _cell_angle_gamma 97.08(3) _cell_formula_units_Z 2 _cell_length_a 8.414(2) _cell_length_b 9.513(2) _cell_length_c 10.497(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 13 _cell_measurement_theta_min 9 _cell_volume 805.1(3) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf--Nonius, 1989)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Enraf--Nonius CAD-4' _diffrn_measurement_method \w/2\q _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 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0587 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 3379 _diffrn_reflns_theta_full 25.97 _diffrn_reflns_theta_max 25.97 _diffrn_reflns_theta_min 2.22 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_T_max 0.9787 _exptl_absorpt_correction_T_min 0.9474 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(XCAD4; Harms & Wocadlo, 1995)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 376 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _refine_diff_density_max 0.185 _refine_diff_density_min -0.226 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 238 _refine_ls_number_reflns 3154 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.011 _refine_ls_R_factor_all 0.1092 _refine_ls_R_factor_gt 0.0498 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.06P)^2^+0.035P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1160 _refine_ls_wR_factor_ref 0.1400 _reflns_number_gt 1822 _reflns_number_total 3154 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6625.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: '_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 2206655 _cod_database_fobs_code 2206655 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_type_symbol F1 0.52063(18) 0.74819(15) -0.07309(14) 0.0470(4) Uani d . 1 F O1 0.7511(3) 1.3189(2) 0.4184(2) 0.0826(8) Uani d . 1 O O2 0.0708(2) 0.32798(18) -0.24166(17) 0.0451(5) Uani d . 1 O O3 -0.1250(3) 0.1022(2) -0.25234(19) 0.0545(5) Uani d D 1 O O4 -0.1734(2) 0.0351(2) -0.06989(19) 0.0544(5) Uani d . 1 O N1 0.7420(3) 1.0744(2) 0.36587(19) 0.0403(5) Uani d . 1 N N2 0.5558(2) 0.8162(2) 0.20153(19) 0.0362(5) Uani d . 1 N N3 0.1515(2) 0.38818(19) 0.16083(18) 0.0316(5) Uani d . 1 N C1 0.7561(4) 1.2033(3) 0.4492(3) 0.0548(8) Uani d . 1 C H1A 0.7711 1.2056 0.5389 0.066 Uiso calc R 1 H C2 0.7396(3) 0.9372(3) 0.4054(2) 0.0435(7) Uani d . 1 C H2B 0.7486 0.9556 0.5008 0.052 Uiso calc R 1 H H2C 0.8322 0.8929 0.3790 0.052 Uiso calc R 1 H C3 0.5846(3) 0.8319(3) 0.3435(2) 0.0440(7) Uani d . 1 C H3A 0.5932 0.7375 0.3623 0.053 Uiso calc R 1 H H3B 0.4937 0.8678 0.3822 0.053 Uiso calc R 1 H C4 0.5543(3) 0.9592(3) 0.1686(3) 0.0491(7) Uani d . 1 C H4A 0.4662 1.0040 0.2039 0.059 Uiso calc R 1 H H4B 0.5366 0.9459 0.0735 0.059 Uiso calc R 1 H C5 0.7127(3) 1.0574(3) 0.2252(2) 0.0458(7) Uani d . 1 C H5A 0.8001 1.0157 0.1856 0.055 Uiso calc R 1 H H5B 0.7093 1.1519 0.2051 0.055 Uiso calc R 1 H C6 0.4412(3) 0.6999(2) 0.1267(2) 0.0329(6) Uani d . 1 C C7 0.4207(3) 0.6684(2) -0.0128(2) 0.0341(6) Uani d . 1 C C8 0.3098(3) 0.5589(2) -0.0912(2) 0.0342(6) Uani d . 1 C H8A 0.2966 0.5468 -0.1823 0.041 Uiso calc R 1 H C9 0.2149(3) 0.4638(2) -0.0344(2) 0.0318(6) Uani d . 1 C C10 0.0981(3) 0.3454(2) -0.1176(2) 0.0335(6) Uani d . 1 C C11 0.0169(3) 0.2494(2) -0.0500(2) 0.0343(6) Uani d . 1 C C12 -0.1022(3) 0.1194(3) -0.1222(3) 0.0391(6) Uani d . 1 C C13 0.0465(3) 0.2758(2) 0.0842(2) 0.0340(6) Uani d . 1 C H13A -0.0094 0.2120 0.1251 0.041 Uiso calc R 1 H C14 0.2387(3) 0.4863(2) 0.1032(2) 0.0298(5) Uani d . 1 C C15 0.3470(3) 0.6054(2) 0.1819(2) 0.0328(6) Uani d . 1 C H15A 0.3561 0.6216 0.2732 0.039 Uiso calc R 1 H C16 0.1684(3) 0.4125(3) 0.3041(2) 0.0364(6) Uani d . 1 C H16A 0.1203 0.4948 0.3491 0.044 Uiso calc R 1 H C17 0.1618(4) 0.2866(3) 0.3656(3) 0.0519(8) Uani d . 1 C H17A 0.1490 0.1901 0.3079 0.062 Uiso calc R 1 H H17B 0.1088 0.2922 0.4435 0.062 Uiso calc R 1 H C18 0.3182(3) 0.3848(3) 0.3778(3) 0.0487(7) Uani d . 1 C H18A 0.3599 0.4500 0.4631 0.058 Uiso calc R 1 H H18B 0.4001 0.3479 0.3274 0.058 Uiso calc R 1 H H3 -0.066(3) 0.174(3) -0.277(3) 0.080 Uiso d 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 F1 0.0499(10) 0.0444(9) 0.0495(9) -0.0030(7) 0.0129(7) 0.0197(7) O1 0.110(2) 0.0391(12) 0.0880(18) 0.0120(13) 0.0026(15) -0.0020(11) O2 0.0506(12) 0.0433(10) 0.0369(10) 0.0042(9) -0.0016(9) 0.0053(8) O3 0.0563(13) 0.0474(12) 0.0469(12) -0.0068(10) -0.0070(10) -0.0012(9) O4 0.0480(12) 0.0434(11) 0.0616(13) -0.0125(9) -0.0044(10) 0.0075(10) N1 0.0481(14) 0.0320(11) 0.0355(12) -0.0028(10) 0.0015(10) 0.0041(9) N2 0.0397(13) 0.0290(10) 0.0375(12) -0.0045(9) -0.0032(9) 0.0128(9) N3 0.0324(12) 0.0250(10) 0.0346(11) -0.0003(8) 0.0035(9) 0.0046(8) C1 0.0558(19) 0.0458(17) 0.0520(18) -0.0011(14) 0.0053(15) -0.0054(14) C2 0.0512(17) 0.0388(14) 0.0351(14) -0.0024(13) -0.0029(12) 0.0074(11) C3 0.0490(17) 0.0368(14) 0.0435(16) -0.0042(12) 0.0013(13) 0.0127(11) C4 0.0552(18) 0.0328(14) 0.0544(17) -0.0023(13) -0.0128(14) 0.0157(12) C5 0.0565(18) 0.0326(14) 0.0466(16) -0.0039(13) 0.0041(13) 0.0135(12) C6 0.0328(14) 0.0262(12) 0.0392(14) 0.0052(10) 0.0005(11) 0.0085(10) C7 0.0351(14) 0.0297(12) 0.0403(14) 0.0046(11) 0.0058(11) 0.0144(11) C8 0.0423(15) 0.0316(12) 0.0296(13) 0.0092(11) 0.0043(11) 0.0074(10) C9 0.0334(14) 0.0258(12) 0.0359(13) 0.0069(10) 0.0030(11) 0.0064(10) C10 0.0322(14) 0.0293(12) 0.0380(15) 0.0095(10) 0.0022(11) 0.0049(10) C11 0.0296(13) 0.0286(12) 0.0412(15) 0.0056(10) 0.0005(11) 0.0023(11) C12 0.0335(15) 0.0319(13) 0.0469(16) 0.0051(11) -0.0017(12) 0.0024(11) C13 0.0312(14) 0.0258(12) 0.0435(15) -0.0003(10) 0.0040(11) 0.0082(10) C14 0.0308(13) 0.0233(11) 0.0354(13) 0.0056(10) 0.0061(10) 0.0057(9) C15 0.0370(14) 0.0275(12) 0.0330(13) 0.0036(10) 0.0039(11) 0.0065(10) C16 0.0401(15) 0.0322(13) 0.0346(13) -0.0007(11) 0.0058(11) 0.0064(10) C17 0.0624(19) 0.0425(15) 0.0472(16) -0.0100(14) -0.0013(14) 0.0176(13) C18 0.0450(17) 0.0559(17) 0.0414(15) 0.0025(14) -0.0017(13) 0.0102(13) 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' F F 0.0171 0.0103 '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 C12 O3 H3 112(2) C1 N1 C5 122.0(2) C1 N1 C2 124.3(2) C5 N1 C2 113.53(19) C6 N2 C3 117.8(2) C6 N2 C4 117.43(19) C3 N2 C4 111.2(2) C13 N3 C14 119.8(2) C13 N3 C16 120.2(2) C14 N3 C16 119.98(18) O1 C1 N1 125.5(3) O1 C1 H1A 117.2 N1 C1 H1A 117.2 N1 C2 C3 111.7(2) N1 C2 H2B 109.3 C3 C2 H2B 109.3 N1 C2 H2C 109.3 C3 C2 H2C 109.3 H2B C2 H2C 107.9 N2 C3 C2 111.0(2) N2 C3 H3A 109.4 C2 C3 H3A 109.4 N2 C3 H3B 109.4 C2 C3 H3B 109.4 H3A C3 H3B 108.0 N2 C4 C5 110.4(2) N2 C4 H4A 109.6 C5 C4 H4A 109.6 N2 C4 H4B 109.6 C5 C4 H4B 109.6 H4A C4 H4B 108.1 N1 C5 C4 109.9(2) N1 C5 H5A 109.7 C4 C5 H5A 109.7 N1 C5 H5B 109.7 C4 C5 H5B 109.7 H5A C5 H5B 108.2 C15 C6 N2 123.4(2) C15 C6 C7 116.0(2) N2 C6 C7 120.6(2) C8 C7 F1 117.5(2) C8 C7 C6 123.6(2) F1 C7 C6 118.9(2) C7 C8 C9 119.9(2) C7 C8 H8A 120.1 C9 C8 H8A 120.1 C14 C9 C8 118.1(2) C14 C9 C10 121.8(2) C8 C9 C10 120.2(2) O2 C10 C11 122.5(2) O2 C10 C9 122.2(2) C11 C10 C9 115.4(2) C13 C11 C10 120.2(2) C13 C11 C12 118.1(2) C10 C11 C12 121.7(2) O4 C12 O3 121.4(2) O4 C12 C11 124.3(2) O3 C12 C11 114.3(2) N3 C13 C11 124.1(2) N3 C13 H13A 118.0 C11 C13 H13A 118.0 N3 C14 C9 118.8(2) N3 C14 C15 120.5(2) C9 C14 C15 120.7(2) C6 C15 C14 121.6(2) C6 C15 H15A 119.2 C14 C15 H15A 119.2 N3 C16 C17 119.7(2) N3 C16 C18 119.6(2) C17 C16 C18 60.49(18) N3 C16 H16A 115.4 C17 C16 H16A 115.4 C18 C16 H16A 115.4 C16 C17 C18 60.02(17) C16 C17 H17A 117.8 C18 C17 H17A 117.8 C16 C17 H17B 117.8 C18 C17 H17B 117.8 H17A C17 H17B 114.9 C16 C18 C17 59.49(17) C16 C18 H18A 117.8 C17 C18 H18A 117.8 C16 C18 H18B 117.8 C17 C18 H18B 117.8 H18A C18 H18B 115.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1 C7 1.363(3) O1 C1 1.216(3) O2 C10 1.267(3) O3 C12 1.328(3) O3 H3 0.900(10) O4 C12 1.206(3) N1 C1 1.326(3) N1 C5 1.439(3) N1 C2 1.452(3) N2 C6 1.398(3) N2 C3 1.454(3) N2 C4 1.475(3) N3 C13 1.341(3) N3 C14 1.398(3) N3 C16 1.459(3) C1 H1A 0.93 C2 C3 1.525(3) C2 H2B 0.97 C2 H2C 0.97 C3 H3A 0.97 C3 H3B 0.97 C4 C5 1.508(4) C4 H4A 0.97 C4 H4B 0.97 C5 H5A 0.97 C5 H5B 0.97 C6 C15 1.388(3) C6 C7 1.415(3) C7 C8 1.359(3) C8 C9 1.406(3) C8 H8A 0.93 C9 C14 1.400(3) C9 C10 1.449(3) C10 C11 1.429(3) C11 C13 1.363(3) C11 C12 1.490(3) C13 H13A 0.93 C14 C15 1.401(3) C15 H15A 0.93 C16 C17 1.477(3) C16 C18 1.485(4) C16 H16A 0.98 C17 C18 1.492(4) C17 H17A 0.97 C17 H17B 0.97 C18 H18A 0.97 C18 H18B 0.97 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O3 H3 O2 0.900(10) 1.687(18) 2.514(3) 151(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 3393929 2 PubChem 4182953