#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/30/2013002.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_2013002 loop_ _publ_author_name 'Zheng, Xiang-Jun' 'Zhao, Hui-Chun' 'Jin, Lin-Pei' _publ_section_title ; Fleroxacin hydrochloride hydrate ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o596 _journal_page_last o597 _journal_paper_doi 10.1107/S0108270102014968 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C17 H19 F3 N3 O3 + , Cl - , H2 O' _chemical_formula_sum 'C17 H21 Cl F3 N3 O4' _chemical_formula_weight 423.82 _chemical_melting_point .552E-305 _chemical_name_common 'fleroxacin hydrochloride hydrate' _chemical_name_systematic ; 4-[3-carboxy-6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-7-quinolyl]- 1-methylpiperazinium chloride hydrate ; _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 _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 104.184(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.961(8) _cell_length_b 7.979(5) _cell_length_c 18.113(11) _cell_measurement_reflns_used 7320 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.03 _cell_measurement_theta_min 1.62 _cell_volume 1816.1(19) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, Year?)' _computing_data_reduction 'SHELXTL (Sheldrick, 1998)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Make Model CCD area-detector' _diffrn_measurement_method '\f and \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 0.032 _diffrn_reflns_av_sigmaI/netI 0.042 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 7320 _diffrn_reflns_theta_full 25.03 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 1.62 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_T_max 0.948 _exptl_absorpt_correction_T_min 0.923 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.32 _refine_diff_density_min -0.22 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 263 _refine_ls_number_reflns 3209 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.008 _refine_ls_R_factor_all 0.067 _refine_ls_R_factor_gt 0.038 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0490P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.089 _refine_ls_wR_factor_ref 0.100 _reflns_number_gt 2103 _reflns_number_total 3209 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ta1382.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: '_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 The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2013002 _cod_database_fobs_code 2013002 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol F1 0.30649(10) 0.42751(16) -0.03141(7) 0.0480(4) Uani d . 1 . . F F2 0.20227(9) 0.08553(15) 0.14874(7) 0.0392(3) Uani d . 1 . . F F3 -0.06282(11) 0.33299(18) 0.19962(8) 0.0578(4) Uani d . 1 . . F N1 -0.01656(13) 0.1435(2) 0.07711(9) 0.0287(4) Uani d . 1 . . N N2 0.36572(14) 0.2335(2) 0.09522(10) 0.0339(5) Uani d . 1 . . N N3 0.58899(14) 0.2668(2) 0.15901(10) 0.0357(5) Uani d . 1 . . N H3A 0.6081 0.1576 0.1682 0.043 Uiso calc R 1 . . H C1 -0.25737(18) 0.2444(3) -0.07653(13) 0.0362(6) Uani d . 1 . . C C2 -0.14409(17) 0.2377(3) -0.03491(12) 0.0306(5) Uani d . 1 . . C C3 -0.06400(17) 0.3163(3) -0.06467(12) 0.0317(5) Uani d . 1 . . C C4 0.04459(16) 0.2960(2) -0.02017(11) 0.0279(5) Uani d . 1 . . C C5 0.06800(16) 0.2083(2) 0.04974(12) 0.0264(5) Uani d . 1 . . C C6 -0.11704(17) 0.1594(3) 0.03428(12) 0.0307(5) Uani d . 1 . . C H6 -0.1716 0.1140 0.0531 0.037 Uiso calc R 1 . . H C7 -0.00443(18) 0.0801(3) 0.15613(12) 0.0349(5) Uani d . 1 . . C H7A 0.0521 -0.0027 0.1674 0.042 Uiso calc R 1 . . H H7B -0.0699 0.0256 0.1598 0.042 Uiso calc R 1 . . H C8 0.02102(19) 0.2194(3) 0.21361(13) 0.0441(6) Uani d . 1 . . C H8A 0.0317 0.1741 0.2646 0.053 Uiso calc R 1 . . H H8B 0.0860 0.2755 0.2099 0.053 Uiso calc R 1 . . H C9 0.17591(17) 0.1851(2) 0.08573(11) 0.0283(5) Uani d . 1 . . C C10 0.25941(16) 0.2518(2) 0.05999(12) 0.0282(5) Uani d . 1 . . C C11 0.22898(17) 0.3470(3) -0.00770(12) 0.0320(5) Uani d . 1 . . C C12 0.12699(17) 0.3653(3) -0.04726(12) 0.0324(5) Uani d . 1 . . C H12 0.1115 0.4245 -0.0929 0.039 Uiso calc R 1 . . H C13 0.44228(17) 0.1808(3) 0.05222(13) 0.0354(6) Uani d . 1 . . C H13A 0.4110 0.1940 -0.0019 0.042 Uiso calc R 1 . . H H13B 0.4597 0.0634 0.0621 0.042 Uiso calc R 1 . . H C14 0.54216(17) 0.2852(3) 0.07522(12) 0.0372(6) Uani d . 1 . . C H14A 0.5932 0.2485 0.0474 0.045 Uiso calc R 1 . . H H14B 0.5255 0.4019 0.0630 0.045 Uiso calc R 1 . . H C15 0.50829(17) 0.3076(3) 0.20329(13) 0.0386(6) Uani d . 1 . . C H15A 0.4920 0.4263 0.1984 0.046 Uiso calc R 1 . . H H15B 0.5386 0.2841 0.2568 0.046 Uiso calc R 1 . . H C16 0.40651(17) 0.2090(3) 0.17677(12) 0.0377(6) Uani d . 1 . . C H16A 0.4201 0.0909 0.1877 0.045 Uiso calc R 1 . . H H16B 0.3544 0.2468 0.2035 0.045 Uiso calc R 1 . . H C17 0.68666(18) 0.3709(3) 0.18475(14) 0.0481(7) Uani d . 1 . . C H17A 0.7372 0.3414 0.1560 0.072 Uiso calc R 1 . . H H17B 0.7173 0.3511 0.2379 0.072 Uiso calc R 1 . . H H17C 0.6684 0.4873 0.1769 0.072 Uiso calc R 1 . . H Cl 0.71815(6) 0.94195(9) 0.16859(5) 0.0677(3) Uani d . 1 . . Cl O1 -0.27944(12) 0.3331(2) -0.14036(9) 0.0495(5) Uani d . 1 . . O H1 -0.2241 0.3702 -0.1482 0.074 Uiso calc R 1 . . H O2 -0.32762(12) 0.1736(2) -0.05476(9) 0.0494(5) Uani d . 1 . . O O3 -0.08495(12) 0.3971(2) -0.12663(9) 0.0475(5) Uani d . 1 . . O O4 -0.52917(16) 0.3095(2) -0.12869(11) 0.0608(5) Uani d D 1 . . O H42 -0.4610(12) 0.261(3) -0.104(2) 0.126(14) Uiso d D 1 . . H H41 -0.5883(16) 0.230(3) -0.138(2) 0.158(18) 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 0.0353(8) 0.0612(9) 0.0485(9) -0.0116(6) 0.0124(6) 0.0168(7) F2 0.0330(7) 0.0490(8) 0.0354(8) 0.0010(6) 0.0078(6) 0.0150(6) F3 0.0535(10) 0.0592(10) 0.0628(10) 0.0079(7) 0.0180(8) -0.0104(7) N1 0.0275(10) 0.0311(10) 0.0282(11) -0.0044(8) 0.0085(8) -0.0006(8) N2 0.0256(10) 0.0527(12) 0.0241(10) -0.0004(9) 0.0075(8) -0.0008(8) N3 0.0291(11) 0.0408(11) 0.0364(12) -0.0020(8) 0.0063(9) 0.0039(9) C1 0.0333(14) 0.0389(14) 0.0353(15) -0.0015(11) 0.0061(11) -0.0080(11) C2 0.0293(12) 0.0318(12) 0.0296(13) -0.0005(10) 0.0050(10) -0.0046(10) C3 0.0336(13) 0.0327(12) 0.0275(13) -0.0006(10) 0.0048(10) -0.0042(10) C4 0.0299(12) 0.0284(12) 0.0249(12) -0.0009(9) 0.0057(9) -0.0018(9) C5 0.0288(12) 0.0242(11) 0.0276(12) -0.0022(9) 0.0094(9) -0.0046(9) C6 0.0279(13) 0.0312(12) 0.0345(13) -0.0037(9) 0.0105(10) -0.0058(10) C7 0.0326(13) 0.0428(14) 0.0319(13) -0.0016(10) 0.0127(10) 0.0076(10) C8 0.0401(15) 0.0616(17) 0.0310(14) 0.0041(13) 0.0092(11) 0.0031(12) C9 0.0320(13) 0.0292(12) 0.0233(12) -0.0004(9) 0.0062(9) 0.0035(9) C10 0.0290(12) 0.0282(12) 0.0269(12) -0.0025(9) 0.0058(10) -0.0040(9) C11 0.0327(13) 0.0341(13) 0.0318(13) -0.0081(10) 0.0130(10) 0.0000(10) C12 0.0349(14) 0.0368(13) 0.0248(12) -0.0022(10) 0.0059(10) 0.0036(10) C13 0.0325(13) 0.0442(14) 0.0306(13) 0.0008(10) 0.0098(10) -0.0035(10) C14 0.0313(13) 0.0505(15) 0.0317(14) -0.0003(11) 0.0112(10) 0.0024(11) C15 0.0343(13) 0.0539(15) 0.0272(13) -0.0046(11) 0.0066(10) 0.0010(11) C16 0.0333(13) 0.0512(15) 0.0292(13) -0.0028(11) 0.0091(10) 0.0043(11) C17 0.0293(14) 0.0618(17) 0.0493(16) -0.0108(12) 0.0025(11) 0.0040(13) Cl 0.0456(4) 0.0556(5) 0.0988(6) 0.0038(3) 0.0116(4) 0.0026(4) O1 0.0355(10) 0.0679(12) 0.0409(11) -0.0031(9) 0.0014(8) 0.0087(9) O2 0.0295(10) 0.0636(12) 0.0533(11) -0.0059(8) 0.0069(8) 0.0027(9) O3 0.0387(10) 0.0653(12) 0.0351(10) -0.0003(8) 0.0025(8) 0.0152(8) O4 0.0493(12) 0.0639(13) 0.0685(14) 0.0028(10) 0.0131(10) 0.0075(10) 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' Cl Cl 0.1484 0.1585 '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 C6 N1 C5 119.25(18) y C6 N1 C7 116.37(18) y C5 N1 C7 123.74(17) y C10 N2 C16 123.92(18) y C10 N2 C13 121.02(18) y C16 N2 C13 112.10(17) y C17 N3 C14 111.39(17) y C17 N3 C15 111.20(18) y C14 N3 C15 110.97(17) y C17 N3 H3A 107.7 ? C14 N3 H3A 107.7 ? C15 N3 H3A 107.7 ? O2 C1 O1 120.8(2) y O2 C1 C2 123.1(2) y O1 C1 C2 116.1(2) y C6 C2 C3 120.0(2) ? C6 C2 C1 118.9(2) ? C3 C2 C1 121.0(2) ? O3 C3 C2 122.8(2) ? O3 C3 C4 121.2(2) ? C2 C3 C4 115.96(19) ? C12 C4 C5 119.80(19) ? C12 C4 C3 118.88(19) ? C5 C4 C3 121.3(2) ? C9 C5 N1 124.17(19) ? C9 C5 C4 116.90(19) ? N1 C5 C4 118.86(18) ? N1 C6 C2 124.4(2) ? N1 C6 H6 117.8 ? C2 C6 H6 117.8 ? N1 C7 C8 111.55(18) ? N1 C7 H7A 109.3 ? C8 C7 H7A 109.3 ? N1 C7 H7B 109.3 ? C8 C7 H7B 109.3 ? H7A C7 H7B 108.0 ? F3 C8 C7 109.08(18) ? F3 C8 H8A 109.9 ? C7 C8 H8A 109.9 ? F3 C8 H8B 109.9 ? C7 C8 H8B 109.9 ? H8A C8 H8B 108.3 ? F2 C9 C10 116.70(18) ? F2 C9 C5 118.85(18) ? C10 C9 C5 124.41(19) ? N2 C10 C9 125.38(19) ? N2 C10 C11 119.58(19) ? C9 C10 C11 115.04(18) ? F1 C11 C12 119.3(2) ? F1 C11 C10 117.45(18) ? C12 C11 C10 123.2(2) ? C11 C12 C4 120.4(2) ? C11 C12 H12 119.8 ? C4 C12 H12 119.8 ? N2 C13 C14 109.99(18) ? N2 C13 H13A 109.7 ? C14 C13 H13A 109.7 ? N2 C13 H13B 109.7 ? C14 C13 H13B 109.7 ? H13A C13 H13B 108.2 ? N3 C14 C13 109.45(18) ? N3 C14 H14A 109.8 ? C13 C14 H14A 109.8 ? N3 C14 H14B 109.8 ? C13 C14 H14B 109.8 ? H14A C14 H14B 108.2 ? N3 C15 C16 112.71(19) ? N3 C15 H15A 109.0 ? C16 C15 H15A 109.0 ? N3 C15 H15B 109.0 ? C16 C15 H15B 109.0 ? H15A C15 H15B 107.8 ? N2 C16 C15 108.96(18) ? N2 C16 H16A 109.9 ? C15 C16 H16A 109.9 ? N2 C16 H16B 109.9 ? C15 C16 H16B 109.9 ? H16A C16 H16B 108.3 ? N3 C17 H17A 109.5 ? N3 C17 H17B 109.5 ? H17A C17 H17B 109.5 ? N3 C17 H17C 109.5 ? H17A C17 H17C 109.5 ? H17B C17 H17C 109.5 ? C1 O1 H1 109.5 ? H42 O4 H41 113.9(15) ? 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 F1 C11 . 1.348(2) y F2 C9 . 1.364(2) y F3 C8 . 1.390(3) y N1 C6 . 1.349(3) y N1 C5 . 1.407(3) y N1 C7 . 1.490(3) y N2 C10 . 1.377(3) y N2 C16 . 1.455(3) y N2 C13 . 1.465(3) y N3 C17 . 1.490(3) y N3 C14 . 1.497(3) y N3 C15 . 1.501(3) y N3 H3A . 0.9100 ? C1 O2 . 1.216(3) y C1 O1 . 1.326(3) y C1 C2 . 1.478(3) ? C2 C6 . 1.367(3) ? C2 C3 . 1.427(3) ? C3 O3 . 1.265(3) y C3 C4 . 1.449(3) ? C4 C12 . 1.394(3) ? C4 C5 . 1.413(3) ? C5 C9 . 1.403(3) ? C6 H6 . 0.9300 ? C7 C8 . 1.504(3) ? C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? C8 H8A . 0.9700 ? C8 H8B . 0.9700 ? C9 C10 . 1.385(3) ? C10 C11 . 1.414(3) ? C11 C12 . 1.348(3) ? C12 H12 . 0.9300 ? C13 C14 . 1.509(3) ? C13 H13A . 0.9700 ? C13 H13B . 0.9700 ? C14 H14A . 0.9700 ? C14 H14B . 0.9700 ? C15 C16 . 1.509(3) ? C15 H15A . 0.9700 ? C15 H15B . 0.9700 ? C16 H16A . 0.9700 ? C16 H16B . 0.9700 ? C17 H17A . 0.9600 ? C17 H17B . 0.9600 ? C17 H17C . 0.9600 ? O1 H1 . 0.8200 ? O4 H42 . 0.969(10) ? O4 H41 . 0.980(10) ? 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 N3 H3A Cl 1_545 0.91 2.234 3.067(3) 152 yes O1 H1 O3 1_555 0.82 1.762 2.524(3) 154 yes O4 H42 O2 1_555 0.97(2) 1.87(2) 2.842(3) 178.11(18) yes O4 H42 O1 1_555 0.97(2) 2.66(2) 3.300(3) 123.94(18) yes O4 H41 Cl 3_565 0.98(2) 2.13(2) 3.111(3) 175.55(17) 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 O2 C1 C2 C6 -5.2(3) O1 C1 C2 C6 174.9(2) O2 C1 C2 C3 177.0(2) O1 C1 C2 C3 -2.8(3) C6 C2 C3 O3 -176.7(2) C1 C2 C3 O3 1.1(3) C6 C2 C3 C4 4.4(3) C1 C2 C3 C4 -177.83(19) O3 C3 C4 C12 -0.9(3) C2 C3 C4 C12 178.02(19) O3 C3 C4 C5 178.87(19) C2 C3 C4 C5 -2.2(3) C6 N1 C5 C9 -173.59(19) C7 N1 C5 C9 15.9(3) C6 N1 C5 C4 3.3(3) C7 N1 C5 C4 -167.17(18) C12 C4 C5 C9 -4.7(3) C3 C4 C5 C9 175.53(18) C12 C4 C5 N1 178.18(18) C3 C4 C5 N1 -1.6(3) C5 N1 C6 C2 -1.1(3) C7 N1 C6 C2 170.08(19) C3 C2 C6 N1 -3.0(3) C1 C2 C6 N1 179.24(19) C6 N1 C7 C8 -102.7(2) C5 N1 C7 C8 68.0(3) N1 C7 C8 F3 62.1(2) N1 C5 C9 F2 4.2(3) C4 C5 C9 F2 -172.79(17) N1 C5 C9 C10 -178.45(19) C4 C5 C9 C10 4.6(3) C16 N2 C10 C9 -28.1(3) C13 N2 C10 C9 130.9(2) C16 N2 C10 C11 151.1(2) C13 N2 C10 C11 -49.9(3) F2 C9 C10 N2 -4.0(3) C5 C9 C10 N2 178.60(19) F2 C9 C10 C11 176.79(17) C5 C9 C10 C11 -0.7(3) N2 C10 C11 F1 -5.3(3) C9 C10 C11 F1 174.02(18) N2 C10 C11 C12 177.3(2) C9 C10 C11 C12 -3.4(3) F1 C11 C12 C4 -174.13(19) C10 C11 C12 C4 3.3(3) C5 C4 C12 C11 1.0(3) C3 C4 C12 C11 -179.2(2) C10 N2 C13 C14 136.7(2) C16 N2 C13 C14 -62.0(2) C17 N3 C14 C13 -178.69(19) C15 N3 C14 C13 -54.2(2) N2 C13 C14 N3 58.3(2) C17 N3 C15 C16 177.85(18) C14 N3 C15 C16 53.3(2) C10 N2 C16 C15 -140.8(2) C13 N2 C16 C15 58.6(2) N3 C15 C16 N2 -54.1(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21107383 2 PubChem 139058694