data_2203334 loop_ _publ_author_name 'Wei, Chang-Mei' 'Jiang, Tao ' 'Li, Yi-Zhi' 'Zhu, Hong-Jun ' 'Wang, Jin-Tang ' _publ_section_title ; 5-(8-Hydroxyquinolyl)guanidinium dichloride ; _journal_issue 3 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o442 _journal_page_last o443 _journal_volume 60 _journal_year 2004 _chemical_formula_moiety 'C10 H12 N4 O 2+, 2Cl -' _chemical_formula_sum 'C10 H12 Cl2 N4 O' _chemical_formula_weight 275.14 _chemical_melting_point 542-543 _chemical_name_common ? _chemical_name_systematic ; 5-(8-hydroxyquinolyl)guanidine dihydrochloride ; _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 2/c ' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 103.30(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 10.715(2) _cell_length_b 11.333(2) _cell_length_c 22.720(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.34 _cell_measurement_theta_min 2.11 _cell_volume 2685.0(10) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Bruker, 2000)' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution SHELXTL _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _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 0.0117 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 2501 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_min 1.84 _diffrn_standards_decay_% 2.54 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.473 _exptl_absorpt_correction_T_max 0.9 _exptl_absorpt_correction_T_min 0.8 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(XPREP in SHELXTL; Bruker, 2000)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1136 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.713 _refine_diff_density_min -0.426 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 2366 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.165 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0453 _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^)+(0.09P)^2^+1.95P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1369 _refine_ls_wR_factor_ref 0.1386 _reflns_number_gt 1885 _reflns_number_total 2366 _reflns_threshold_expression I>2\s(I) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 1.2590(3) 1.0302(3) 0.42151(14) 0.0341(5) Uani d U 1 . . C H1 1.3457 1.0492 0.4295 0.041 Uiso calc R 1 . . H C2 1.1759(3) 1.0784(3) 0.37068(14) 0.0340(5) Uani d U 1 . . C H2 1.2050 1.1317 0.3457 0.041 Uiso calc R 1 . . H C3 1.0491(3) 1.0440(3) 0.35888(13) 0.0323(5) Uani d U 1 . . C H3 0.9932 1.0723 0.3242 0.039 Uiso calc R 1 . . H C4 1.0018(3) 0.9689(3) 0.39685(13) 0.0304(4) Uani d U 1 . . C C5 0.8718(3) 0.9363(3) 0.38835(13) 0.0325(4) Uani d U 1 . . C C6 0.8358(3) 0.8577(3) 0.42718(13) 0.0340(5) Uani d U 1 . . C H6 0.7508 0.8332 0.4200 0.041 Uiso calc R 1 . . H C7 0.9244(3) 0.8139(3) 0.47745(13) 0.0316(5) Uani d U 1 . . C H7 0.8974 0.7622 0.5038 0.038 Uiso calc R 1 . . H C8 1.0539(3) 0.8471(3) 0.48843(12) 0.0285(4) Uani d U 1 . . C C9 1.0878(3) 0.9217(3) 0.44814(12) 0.0282(4) Uani d U 1 . . C C10 0.7523(3) 0.9455(3) 0.28186(13) 0.0350(5) Uani d U 1 . . C Cl1 0.07744(8) 0.70303(7) 0.33352(3) 0.0428(3) Uani d . 1 . . Cl Cl2 0.46422(8) 0.84034(7) 0.37643(4) 0.0424(3) Uani d . 1 . . Cl N1 1.2178(2) 0.9594(2) 0.45793(11) 0.0320(4) Uani d U 1 . . N H1A 1.2717 0.9341 0.4895 0.038 Uiso calc R 1 . . H N2 0.7795(2) 0.9870(2) 0.33973(11) 0.0336(5) Uani d U 1 . . N H2A 0.7381 1.0479 0.3474 0.040 Uiso calc R 1 . . H N3 0.6642(2) 1.0026(3) 0.24133(12) 0.0418(6) Uani d U 1 . . N H3A 0.6461 0.9800 0.2042 0.050 Uiso calc R 1 . . H H3B 0.6252 1.0623 0.2522 0.050 Uiso calc R 1 . . H N4 0.8161(3) 0.8536(3) 0.26882(13) 0.0481(7) Uani d U 1 . . N H4A 0.8015 0.8276 0.2323 0.058 Uiso calc R 1 . . H H4B 0.8724 0.8197 0.2968 0.058 Uiso calc R 1 . . H O1 1.14419(19) 0.8084(2) 0.53612(9) 0.0366(5) Uani d U 1 . . O H1C 1.1056 0.7553 0.5597 0.055 Uiso d 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 C1 0.0259(9) 0.0360(9) 0.0391(9) 0.0030(8) 0.0047(8) -0.0011(8) C2 0.0262(9) 0.0367(10) 0.0378(9) 0.0021(8) 0.0045(8) 0.0004(8) C3 0.0272(9) 0.0333(9) 0.0346(9) 0.0010(8) 0.0036(8) -0.0008(8) C4 0.0259(8) 0.0326(8) 0.0309(8) 0.0037(7) 0.0032(7) -0.0042(7) C5 0.0287(8) 0.0355(8) 0.0314(8) 0.0034(7) 0.0028(7) -0.0051(7) C6 0.0292(9) 0.0397(9) 0.0323(9) -0.0013(8) 0.0058(8) -0.0023(8) C7 0.0274(9) 0.0375(9) 0.0295(9) -0.0010(8) 0.0056(8) -0.0006(8) C8 0.0258(8) 0.0330(9) 0.0262(8) 0.0015(7) 0.0047(7) -0.0018(7) C9 0.0224(7) 0.0324(8) 0.0285(7) 0.0047(7) 0.0032(6) -0.0032(7) C10 0.0322(9) 0.0394(10) 0.0307(9) 0.0059(9) 0.0014(8) -0.0037(8) Cl1 0.0510(5) 0.0403(5) 0.0358(4) 0.0149(4) 0.0072(3) 0.0044(3) Cl2 0.0532(5) 0.0367(5) 0.0358(4) 0.0022(4) 0.0071(3) 0.0054(3) N1 0.0249(8) 0.0343(9) 0.0351(8) 0.0050(7) 0.0036(7) -0.0020(7) N2 0.0311(8) 0.0365(9) 0.0308(8) 0.0060(8) 0.0021(7) -0.0068(7) N3 0.0345(12) 0.0497(14) 0.0356(12) 0.0115(11) -0.0036(10) -0.0003(11) N4 0.0510(14) 0.0502(14) 0.0364(12) 0.0137(12) -0.0037(11) -0.0160(11) O1 0.0337(10) 0.0428(11) 0.0296(10) 0.0031(9) -0.0007(8) 0.0072(8) 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' 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N1 C1 C2 . . 121.5(3) ? N1 C1 H1 . . 119.3 ? C2 C1 H1 . . 119.3 ? C3 C2 C1 . . 117.6(3) ? C3 C2 H2 . . 121.2 ? C1 C2 H2 . . 121.2 ? C2 C3 C4 . . 122.4(3) ? C2 C3 H3 . . 118.8 ? C4 C3 H3 . . 118.8 ? C3 C4 C5 . . 124.4(3) yes C3 C4 C9 . . 118.8(3) ? C5 C4 C9 . . 116.7(3) ? C6 C5 C4 . . 119.9(3) ? C6 C5 N2 . . 120.9(3) ? C4 C5 N2 . . 119.3(3) yes C5 C6 C7 . . 121.2(3) ? C5 C6 H6 . . 119.4 ? C7 C6 H6 . . 119.4 ? C6 C7 C8 . . 120.5(3) ? C6 C7 H7 . . 119.7 ? C8 C7 H7 . . 119.7 ? O1 C8 C9 . . 119.4(2) ? O1 C8 C7 . . 123.6(3) yes C9 C8 C7 . . 117.1(3) ? C8 C9 C4 . . 124.5(3) yes C8 C9 N1 . . 119.1(2) yes C4 C9 N1 . . 116.4(3) ? N4 C10 N3 . . 123.6(3) ? N4 C10 N2 . . 118.8(3) yes N3 C10 N2 . . 117.5(3) ? C1 N1 C9 . . 123.3(3) ? C1 N1 H1A . . 118.4 ? C9 N1 H1A . . 118.4 ? C10 N2 C5 . . 124.5(3) ? C10 N2 H2A . . 117.8 ? C5 N2 H2A . . 117.8 ? C10 N3 H3A . . 120.0 ? C10 N3 H3B . . 120.0 ? H3A N3 H3B . . 120.0 ? C10 N4 H4A . . 120.0 ? C10 N4 H4B . . 120.0 ? H4A N4 H4B . . 120.0 ? C8 O1 H1C . . 109.2 ? 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 C1 N1 . 1.300(4) yes C1 C2 . 1.397(4) ? C1 H1 . 0.9300 ? C2 C3 . 1.380(4) ? C2 H2 . 0.9300 ? C3 C4 . 1.388(4) yes C3 H3 . 0.9300 ? C4 C5 . 1.412(4) ? C4 C9 . 1.413(4) yes C5 C6 . 1.370(4) ? C5 N2 . 1.423(4) yes C6 C7 . 1.398(4) ? C6 H6 . 0.9300 ? C7 C8 . 1.404(4) ? C7 H7 . 0.9300 ? C8 O1 . 1.349(3) yes C8 C9 . 1.356(4) ? C9 N1 . 1.426(4) yes C10 N4 . 1.316(4) yes C10 N3 . 1.326(4) yes C10 N2 . 1.363(4) yes N1 H1A . 0.8600 ? N2 H2A . 0.8600 ? N3 H3A . 0.8600 ? N3 H3B . 0.8600 ? N4 H4A . 0.8600 ? N4 H4B . 0.8600 ? O1 H1C . 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 N2 H2A Cl1 3 0.86 2.43 3.250(3) 159.7 N3 H3B Cl1 3 0.86 2.58 3.362(3) 151.7 N3 H3A Cl2 2_655 0.86 2.50 3.277(3) 150.3 N4 H4A Cl1 2_655 0.86 2.61 3.293(3) 137.3 N4 H4B Cl1 1_655 0.86 2.54 3.320(3) 152.1 O1 H1C Cl2 7_666 0.96 2.08 3.033(2) 169.9