#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/42/2204251.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_2204251 loop_ _publ_author_name 'Yudong, Shen' 'Haiqiang, Wu' 'Xianzhang, Bu' 'Lianquan, Gu' _publ_section_title ; 2-Amino-7-chloro-1,8-naphthyridine ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1641 _journal_page_last o1642 _journal_paper_doi 10.1107/S1600536804020884 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C8 H6 Cl N3' _chemical_formula_moiety 'C8 H6 Cl N3' _chemical_formula_sum 'C8 H6 Cl N3' _chemical_formula_weight 179.61 _chemical_melting_point .452E-305 _chemical_name_systematic ; 2-amino-7-chloro-1,8-naphthyridine ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 91.012(17) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.906(7) _cell_length_b 12.538(13) _cell_length_c 9.099(9) _cell_measurement_reflns_used 3155 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.22 _cell_measurement_theta_min 2.77 _cell_volume 787.7(14) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker,1998)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'SHELXTL (Bruker, 1998)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker SMART 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 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 4791 _diffrn_reflns_theta_full 27.22 _diffrn_reflns_theta_max 27.22 _diffrn_reflns_theta_min 2.77 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.423 _exptl_absorpt_correction_T_max 0.8661 _exptl_absorpt_correction_T_min 0.8164 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 368 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.287 _refine_diff_density_min -0.250 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 109 _refine_ls_number_reflns 1749 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.045 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0357 _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^)+(0.0589P)^2^+0.2069P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1026 _refine_ls_wR_factor_ref 0.1081 _reflns_number_gt 1498 _reflns_number_total 1749 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ww6272.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2204251 _cod_database_fobs_code 2204251 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 Cl1 1.14367(7) 0.81937(4) 0.55480(5) 0.06047(19) Uani d . 1 Cl N1 0.92935(19) 0.66304(10) 0.45997(13) 0.0409(3) Uani d . 1 N N2 0.71727(17) 0.52888(10) 0.39707(13) 0.0406(3) Uani d . 1 N C2 1.2349(2) 0.68261(13) 0.33712(19) 0.0507(4) Uani d . 1 C H2 1.3502 0.7204 0.3293 0.061 Uiso calc R 1 H N3 0.5031(2) 0.39486(12) 0.34545(16) 0.0556(4) Uani d . 1 N H3A 0.4302 0.4187 0.4137 0.067 Uiso calc R 1 H H3B 0.4684 0.3396 0.2956 0.067 Uiso calc R 1 H C5 0.8888(2) 0.57736(11) 0.37248(14) 0.0368(3) Uani d . 1 C C1 1.0958(2) 0.71003(13) 0.44037(16) 0.0434(3) Uani d . 1 C C4 1.0192(2) 0.54205(12) 0.26415(15) 0.0399(3) Uani d . 1 C C8 0.6709(2) 0.44386(13) 0.31670(16) 0.0425(3) Uani d . 1 C C3 1.1932(2) 0.59769(14) 0.24847(18) 0.0484(4) Uani d . 1 C H3 1.2805 0.5767 0.1774 0.058 Uiso calc R 1 H C6 0.9629(2) 0.45210(13) 0.17916(16) 0.0465(4) Uani d . 1 C H6 1.0436 0.4267 0.1063 0.056 Uiso calc R 1 H C7 0.7931(3) 0.40338(14) 0.20357(17) 0.0477(4) Uani d . 1 C H7 0.7554 0.3444 0.1481 0.057 Uiso calc R 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 Cl1 0.0608(3) 0.0563(3) 0.0647(3) -0.01606(19) 0.0119(2) -0.01139(19) N1 0.0409(6) 0.0425(7) 0.0395(6) 0.0004(5) 0.0062(5) 0.0014(5) N2 0.0381(6) 0.0451(7) 0.0387(6) 0.0002(5) 0.0059(5) -0.0019(5) C2 0.0427(8) 0.0528(9) 0.0571(9) -0.0042(7) 0.0129(7) 0.0069(7) N3 0.0478(7) 0.0600(9) 0.0593(8) -0.0114(7) 0.0097(6) -0.0190(7) C5 0.0371(7) 0.0403(7) 0.0331(6) 0.0045(5) 0.0043(5) 0.0057(5) C1 0.0453(8) 0.0423(8) 0.0428(7) -0.0013(6) 0.0054(6) 0.0040(6) C4 0.0416(7) 0.0427(8) 0.0358(7) 0.0075(6) 0.0076(5) 0.0068(6) C8 0.0419(8) 0.0468(8) 0.0388(7) 0.0017(6) 0.0020(6) -0.0003(6) C3 0.0464(8) 0.0525(9) 0.0469(8) 0.0044(7) 0.0178(7) 0.0060(7) C6 0.0540(9) 0.0485(9) 0.0375(7) 0.0104(7) 0.0121(6) 0.0007(6) C7 0.0564(9) 0.0463(9) 0.0405(8) 0.0022(7) 0.0047(6) -0.0066(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' 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 C1 N1 C5 116.60(13) C8 N2 C5 118.18(12) C3 C2 C1 116.66(15) C3 C2 H2 121.7 C1 C2 H2 121.7 C8 N3 H3A 120.0 C8 N3 H3B 120.0 H3A N3 H3B 120.0 N2 C5 N1 115.39(12) N2 C5 C4 122.91(14) N1 C5 C4 121.70(14) N1 C1 C2 126.68(16) N1 C1 Cl1 115.45(12) C2 C1 Cl1 117.87(13) C3 C4 C5 118.20(15) C3 C4 C6 124.69(14) C5 C4 C6 117.11(14) N2 C8 N3 117.42(14) N2 C8 C7 122.66(15) N3 C8 C7 119.92(15) C2 C3 C4 120.14(14) C2 C3 H3 119.9 C4 C3 H3 119.9 C7 C6 C4 120.22(14) C7 C6 H6 119.9 C4 C6 H6 119.9 C6 C7 C8 118.91(16) C6 C7 H7 120.5 C8 C7 H7 120.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C1 1.749(2) ? N1 C1 1.307(2) yes N1 C5 1.363(2) yes N2 C8 1.329(2) yes N2 C5 1.354(2) yes C2 C3 1.363(3) yes C2 C1 1.399(2) yes C2 H2 0.9300 ? N3 C8 1.342(2) ? N3 H3A 0.8600 ? N3 H3B 0.8600 ? C5 C4 1.418(2) yes C4 C3 1.398(2) yes C4 C6 1.418(2) yes C8 C7 1.435(2) yes C3 H3 0.9300 ? C6 C7 1.344(3) yes C6 H6 0.9300 ? C7 H7 0.9300 ? 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 N3 H3A N2 3_666 0.86 2.12 2.974(3) 172 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 C8 N2 C5 N1 -178.99(13) C8 N2 C5 C4 0.7(2) C1 N1 C5 N2 178.74(13) C1 N1 C5 C4 -1.0(2) C5 N1 C1 C2 1.2(2) C5 N1 C1 Cl1 -179.78(10) C3 C2 C1 N1 -0.5(3) C3 C2 C1 Cl1 -179.43(12) N2 C5 C4 C3 -179.67(13) N1 C5 C4 C3 0.0(2) N2 C5 C4 C6 0.3(2) N1 C5 C4 C6 179.98(13) C5 N2 C8 N3 178.06(14) C5 N2 C8 C7 -1.4(2) C1 C2 C3 C4 -0.6(2) C5 C4 C3 C2 0.8(2) C6 C4 C3 C2 -179.18(15) C3 C4 C6 C7 179.37(15) C5 C4 C6 C7 -0.6(2) C4 C6 C7 C8 -0.1(2) N2 C8 C7 C6 1.1(2) N3 C8 C7 C6 -178.33(15) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 76834 2 PubChem 85199