#------------------------------------------------------------------------------ #$Date: 2020-04-21 05:24:35 +0300 (Tue, 21 Apr 2020) $ #$Revision: 250975 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240365.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7240365 loop_ _publ_author_name 'Ibrahim, Hamada Mohamed' 'Behbehani, Haider' 'Ahmed Arafa, Wael Abdelgayed' _publ_section_title ; A facile, practical and metal-free microwave-assisted protocol for mono- and bis-[1,2,4]triazolo[1,5-a]pyridines synthesis utilizing 1-amino-2-imino-pyridine derivatives as versatile precursors ; _journal_issue 26 _journal_name_full 'RSC Advances' _journal_page_first 15554 _journal_paper_doi 10.1039/D0RA02256J _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C12 H8 Cl N3' _chemical_formula_sum 'C12 H8 Cl N3' _chemical_formula_weight 229.67 _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _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_block_doi 10.5517/ccdc.csd.cc24jtvc _audit_update_record ; 2020-02-06 deposited with the CCDC. 2020-04-13 downloaded from the CCDC. ; _cell_angle_alpha 90.0000 _cell_angle_beta 95.964(7) _cell_angle_gamma 90.0000 _cell_formula_units_Z 4 _cell_length_a 3.8851(9) _cell_length_b 19.350(4) _cell_length_c 14.116(3) _cell_measurement_reflns_used 2415 _cell_measurement_temperature 293 _cell_measurement_theta_max 24.98 _cell_measurement_theta_min 3.09 _cell_volume 1055.5(4) _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4' _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4' _computing_molecular_graphics 'CrystalStructure 4.0' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 293 _diffrn_detector_area_resol_mean 10.000 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0858 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5853 _diffrn_reflns_theta_full 25.01 _diffrn_reflns_theta_max 25.00 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.333 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_correction_T_min 0.037 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Needle _exptl_crystal_F_000 472.00 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.030 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.360 _refine_diff_density_min -0.370 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 145 _refine_ls_number_reflns 1863 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0782 _refine_ls_shift/su_max 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1382P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.2332 _reflns_number_gt 1153 _reflns_number_total 1863 _reflns_threshold_expression F^2^>2.0\s(F^2^) _cod_data_source_file d0ra02256j1.cif _cod_data_source_block User-defined_CCDC3 _cod_database_code 7240365 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.7195(4) -0.02363(6) 0.32993(8) 0.0676(6) Uani 1.0 4 d . . . N1 N 1.1163(11) 0.4056(2) 0.5227(3) 0.0562(11) Uani 1.0 4 d . . . N2 N 0.5371(13) 0.3201(2) 0.2331(3) 0.0723(13) Uani 1.0 4 d . . . N3 N 0.8201(13) 0.4520(2) 0.3887(3) 0.0703(13) Uani 1.0 4 d . . . C1 C 0.9352(12) 0.1975(3) 0.4185(3) 0.0480(11) Uani 1.0 4 d . . . C2 C 0.9760(13) 0.1760(3) 0.3268(3) 0.0531(12) Uani 1.0 4 d . . . C3 C 0.9111(13) 0.1078(3) 0.2988(3) 0.0559(12) Uani 1.0 4 d . . . C4 C 0.8030(12) 0.0617(3) 0.3636(3) 0.0502(11) Uani 1.0 4 d . . . C5 C 0.7666(13) 0.0813(3) 0.4570(3) 0.0555(12) Uani 1.0 4 d . . . C6 C 0.8320(13) 0.1490(3) 0.4828(3) 0.0557(13) Uani 1.0 4 d . . . C7 C 1.0046(12) 0.2698(2) 0.4518(3) 0.0458(11) Uani 1.0 4 d . . . C8 C 0.8846(12) 0.3276(3) 0.3992(3) 0.0503(12) Uani 1.0 4 d . . . C9 C 0.9407(13) 0.3949(3) 0.4365(3) 0.0520(12) Uani 1.0 4 d . . . C10 C 1.2320(13) 0.3492(3) 0.5708(3) 0.0572(13) Uani 1.0 4 d . . . C11 C 1.1812(13) 0.2819(3) 0.5414(3) 0.0547(12) Uani 1.0 4 d . . . C12 C 0.6904(14) 0.3219(3) 0.3061(3) 0.0563(13) Uani 1.0 4 d . . . H2 H 1.0477 0.2076 0.2832 0.0637 Uiso 1.0 4 calc R . . H3A H 0.8572 0.4922 0.4136 0.0844 Uiso 1.0 4 calc R . . H3B H 0.7063 0.4481 0.3334 0.0844 Uiso 1.0 4 calc R . . H3 H 0.9406 0.0936 0.2372 0.0670 Uiso 1.0 4 calc R . . H5 H 0.6996 0.0495 0.5009 0.0667 Uiso 1.0 4 calc R . . H6 H 0.8067 0.1627 0.5448 0.0668 Uiso 1.0 4 calc R . . H10 H 1.3586 0.3562 0.6296 0.0686 Uiso 1.0 4 calc R . . H11 H 1.2625 0.2453 0.5803 0.0656 Uiso 1.0 4 calc R . . 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 0.0854(11) 0.0556(8) 0.0595(8) -0.0095(6) -0.0040(6) -0.0027(6) N1 0.071(3) 0.055(3) 0.0407(19) -0.0035(19) -0.0003(18) -0.0040(17) N2 0.099(4) 0.060(3) 0.052(3) -0.004(3) -0.015(3) 0.001(2) N3 0.107(4) 0.050(3) 0.050(3) -0.004(3) -0.013(3) 0.0011(19) C1 0.054(3) 0.050(3) 0.040(2) 0.0016(19) 0.0017(19) 0.002(2) C2 0.063(3) 0.056(3) 0.040(3) -0.002(3) 0.0057(19) 0.008(2) C3 0.068(4) 0.059(3) 0.041(2) 0.003(3) 0.003(2) -0.000(3) C4 0.050(3) 0.051(3) 0.048(3) -0.002(2) -0.0048(19) -0.001(2) C5 0.063(4) 0.055(3) 0.048(3) -0.004(3) 0.003(2) 0.007(3) C6 0.065(4) 0.057(3) 0.044(3) 0.003(3) 0.004(2) -0.001(3) C7 0.055(3) 0.049(3) 0.0340(19) 0.0001(19) 0.0070(19) 0.0020(18) C8 0.059(3) 0.053(3) 0.037(2) -0.008(2) -0.000(2) -0.002(2) C9 0.062(4) 0.051(3) 0.042(3) -0.002(2) 0.002(2) 0.000(2) C10 0.060(4) 0.071(4) 0.039(3) -0.000(3) -0.001(2) -0.005(3) C11 0.066(4) 0.055(3) 0.042(3) 0.006(3) -0.003(2) 0.001(3) C12 0.077(4) 0.045(3) 0.045(3) -0.005(3) -0.001(3) 0.001(2) 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.1484 0.1585 ; International Tables for Crystallography (1992, 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C9 N1 C10 116.4(4) yes . . . C2 C1 C6 118.4(4) yes . . . C2 C1 C7 122.8(4) yes . . . C6 C1 C7 118.8(4) yes . . . C1 C2 C3 120.9(4) yes . . . C2 C3 C4 119.0(4) yes . . . Cl1 C4 C3 119.6(4) yes . . . Cl1 C4 C5 118.9(4) yes . . . C3 C4 C5 121.4(4) yes . . . C4 C5 C6 118.4(5) yes . . . C1 C6 C5 121.8(4) yes . . . C1 C7 C8 123.0(4) yes . . . C1 C7 C11 119.9(4) yes . . . C8 C7 C11 117.0(4) yes . . . C7 C8 C9 120.6(4) yes . . . C7 C8 C12 122.4(4) yes . . . C9 C8 C12 116.9(4) yes . . . N1 C9 N3 116.2(4) yes . . . N1 C9 C8 121.5(4) yes . . . N3 C9 C8 122.3(4) yes . . . N1 C10 C11 126.1(4) yes . . . C7 C11 C10 118.3(4) yes . . . N2 C12 C8 177.5(5) yes . . . C9 N3 H3A 119.999 no . . . C9 N3 H3B 119.991 no . . . H3A N3 H3B 120.010 no . . . C1 C2 H2 119.527 no . . . C3 C2 H2 119.547 no . . . C2 C3 H3 120.504 no . . . C4 C3 H3 120.506 no . . . C4 C5 H5 120.778 no . . . C6 C5 H5 120.783 no . . . C1 C6 H6 119.113 no . . . C5 C6 H6 119.121 no . . . N1 C10 H10 116.948 no . . . C11 C10 H10 116.943 no . . . C7 C11 H11 120.864 no . . . C10 C11 H11 120.871 no . . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Cl1 C4 1.740(5) yes . . N1 C9 1.347(6) yes . . N1 C10 1.338(6) yes . . N2 C12 1.135(6) yes . . N3 C9 1.353(6) yes . . C1 C2 1.384(6) yes . . C1 C6 1.393(7) yes . . C1 C7 1.493(6) yes . . C2 C3 1.394(7) yes . . C3 C4 1.374(7) yes . . C4 C5 1.393(6) yes . . C5 C6 1.375(7) yes . . C7 C8 1.395(6) yes . . C7 C11 1.395(6) yes . . C8 C9 1.413(6) yes . . C8 C12 1.449(6) yes . . C10 C11 1.375(7) yes . . N3 H3A 0.860 no . . N3 H3B 0.860 no . . C2 H2 0.930 no . . C3 H3 0.930 no . . C5 H5 0.930 no . . C6 H6 0.930 no . . C10 H10 0.930 no . . C11 H11 0.930 no . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 N1 C7 2.829(6) no . . N2 N3 3.471(6) no . . N2 C2 3.458(7) no . . N2 C7 3.551(6) no . . N2 C9 3.444(6) no . . N3 C10 3.502(6) no . . N3 C12 2.797(6) no . . C1 C4 2.772(6) no . . C1 C12 2.985(6) no . . C2 C5 2.776(7) no . . C2 C8 3.138(7) no . . C2 C12 3.037(7) no . . C3 C6 2.764(7) no . . C6 C11 2.985(7) no . . C8 C10 2.681(6) no . . C9 C11 2.749(7) no . . Cl1 N2 3.279(5) no . 2_645 Cl1 N3 3.577(5) no . 2_645 N1 N3 3.597(7) no . 1_655 N1 N3 3.026(6) no . 3_766 N1 C9 3.549(7) no . 1_655 N2 Cl1 3.279(5) no . 2_655 N2 C11 3.514(6) no . 4_454 N2 C12 3.548(8) no . 1_455 N3 Cl1 3.577(5) no . 2_655 N3 N1 3.597(7) no . 1_455 N3 N1 3.026(6) no . 3_766 C7 C11 3.568(7) no . 1_455 C8 C12 3.520(7) no . 1_655 C9 N1 3.549(7) no . 1_455 C11 N2 3.514(6) no . 4_655 C11 C7 3.568(7) no . 1_655 C12 N2 3.548(8) no . 1_655 C12 C8 3.520(7) no . 1_455 Cl1 H3 2.7981 no . . Cl1 H5 2.8047 no . . N1 H3A 2.4225 no . . N1 H3B 3.0773 no . . N1 H11 3.2407 no . . N2 H2 2.9795 no . . N2 H3B 2.8939 no . . C1 H3 3.2556 no . . C1 H5 3.2575 no . . C1 H11 2.6623 no . . C2 H6 3.2235 no . . C3 H5 3.2506 no . . C4 H2 3.2232 no . . C4 H6 3.2174 no . . C5 H3 3.2516 no . . C6 H2 3.2275 no . . C6 H11 2.7735 no . . C7 H2 2.6870 no . . C7 H6 2.6123 no . . C7 H10 3.2047 no . . C8 H2 2.9466 no . . C8 H3A 3.1941 no . . C8 H3B 2.5773 no . . C8 H11 3.2322 no . . C9 H10 3.1155 no . . C11 H6 2.7302 no . . C12 H2 2.6490 no . . C12 H3B 2.4702 no . . H2 H3 2.3252 no . . H5 H6 2.3032 no . . H6 H11 2.4002 no . . H10 H11 2.2745 no . . Cl1 H3B 2.7493 no . 2_645 Cl1 H3B 3.4144 no . 2_745 Cl1 H5 3.0685 no . 3_656 Cl1 H5 3.1509 no . 3_756 N1 H3A 2.1710 no . 3_766 N1 H3B 3.5120 no . 3_766 N1 H3 3.1729 no . 4_555 N1 H10 3.5746 no . 1_455 N2 H2 3.0215 no . 1_455 N2 H6 2.9753 no . 4_554 N2 H11 2.6297 no . 4_454 N3 H3A 3.1301 no . 3_766 N3 H3 3.4465 no . 2_755 C2 H10 3.5360 no . 4_454 C2 H10 3.3479 no . 4_554 C3 H10 3.1199 no . 4_454 C3 H10 3.1746 no . 4_554 C4 H5 3.5881 no . 3_656 C4 H5 3.3543 no . 3_756 C5 H5 3.2038 no . 3_656 C5 H5 3.2871 no . 3_756 C6 H11 3.3016 no . 1_455 C7 H11 3.5936 no . 1_455 C9 H3A 3.0857 no . 3_766 C9 H3B 3.5952 no . 1_655 C10 H2 3.3410 no . 4_555 C10 H3A 3.0989 no . 3_766 C10 H3 2.9289 no . 4_555 C10 H10 3.5786 no . 1_455 C11 H2 3.5115 no . 4_555 C11 H6 3.3472 no . 1_655 C12 H2 3.3265 no . 1_455 H2 N2 3.0215 no . 1_655 H2 C10 3.3410 no . 4_554 H2 C11 3.5115 no . 4_554 H2 C12 3.3265 no . 1_655 H2 H10 3.4912 no . 4_454 H2 H10 2.8694 no . 4_554 H2 H11 3.1982 no . 4_554 H3A N1 2.1710 no . 3_766 H3A N3 3.1301 no . 3_766 H3A C9 3.0857 no . 3_766 H3A C10 3.0989 no . 3_766 H3A H3A 2.5893 no . 3_766 H3A H3 3.0580 no . 2_755 H3A H10 3.0944 no . 3_766 H3B Cl1 2.7493 no . 2_655 H3B Cl1 3.4144 no . 2_755 H3B N1 3.5120 no . 3_766 H3B C9 3.5952 no . 1_455 H3B H3 3.3304 no . 2_755 H3 N1 3.1729 no . 4_554 H3 N3 3.4465 no . 2_745 H3 C10 2.9289 no . 4_554 H3 H3A 3.0580 no . 2_745 H3 H3B 3.3304 no . 2_745 H3 H10 2.7656 no . 4_454 H3 H10 2.5301 no . 4_554 H5 Cl1 3.0685 no . 3_656 H5 Cl1 3.1509 no . 3_756 H5 C4 3.5881 no . 3_656 H5 C4 3.3543 no . 3_756 H5 C5 3.2038 no . 3_656 H5 C5 3.2871 no . 3_756 H5 H5 2.4621 no . 3_656 H5 H5 3.0207 no . 3_756 H6 N2 2.9753 no . 4_555 H6 C11 3.3472 no . 1_455 H6 H11 2.7384 no . 1_455 H10 N1 3.5746 no . 1_655 H10 C2 3.3479 no . 4_555 H10 C2 3.5360 no . 4_655 H10 C3 3.1746 no . 4_555 H10 C3 3.1199 no . 4_655 H10 C10 3.5786 no . 1_655 H10 H2 2.8694 no . 4_555 H10 H2 3.4912 no . 4_655 H10 H3A 3.0944 no . 3_766 H10 H3 2.5301 no . 4_555 H10 H3 2.7656 no . 4_655 H11 N2 2.6297 no . 4_655 H11 C6 3.3016 no . 1_655 H11 C7 3.5936 no . 1_655 H11 H2 3.1982 no . 4_555 H11 H6 2.7384 no . 1_655 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N3 H3A N1 . . 3_766 3.026(6) 0.860 2.171 173.1 no 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 _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C9 N1 C10 C11 -1.6(7) no . . . . C10 N1 C9 N3 179.1(4) no . . . . C10 N1 C9 C8 -0.4(7) no . . . . C2 C1 C6 C5 -0.8(7) no . . . . C6 C1 C2 C3 0.8(7) no . . . . C2 C1 C7 C8 46.2(7) no . . . . C2 C1 C7 C11 -137.3(4) no . . . . C7 C1 C2 C3 179.4(4) no . . . . C6 C1 C7 C8 -135.2(5) no . . . . C6 C1 C7 C11 41.3(6) no . . . . C7 C1 C6 C5 -179.5(4) no . . . . C1 C2 C3 C4 0.5(7) no . . . . C2 C3 C4 Cl1 179.8(4) no . . . . C2 C3 C4 C5 -1.8(7) no . . . . Cl1 C4 C5 C6 -179.8(3) no . . . . C3 C4 C5 C6 1.8(7) no . . . . C4 C5 C6 C1 -0.5(7) no . . . . C1 C7 C8 C9 176.3(4) no . . . . C1 C7 C8 C12 -1.9(7) no . . . . C1 C7 C11 C10 -178.2(4) no . . . . C8 C7 C11 C10 -1.5(7) no . . . . C11 C7 C8 C9 -0.3(7) no . . . . C11 C7 C8 C12 -178.5(4) no . . . . C7 C8 C9 N1 1.3(7) no . . . . C7 C8 C9 N3 -178.2(4) no . . . . C12 C8 C9 N1 179.6(4) no . . . . C12 C8 C9 N3 0.1(7) no . . . . N1 C10 C11 C7 2.6(8) no . . . .