#------------------------------------------------------------------------------ #$Date: 2024-03-28 03:27:26 +0200 (Thu, 28 Mar 2024) $ #$Revision: 290691 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/31/7063113.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_7063113 loop_ _publ_author_name 'Kuang, Baolong' 'Lu, Zu-Jia' 'Zhao, Binshan' 'Wang, Tingwei' 'Sun, Mou' 'Zhang, Chao' 'Xu, Meiqi' 'Yu, Qiyao' 'Zhang, Jianguo' _publ_section_title ; Novel energetic pyridine-2-carbohydrazide copper perchlorate complex：synthesis, cationic ligand structure and properties ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D4NJ01095G _journal_year 2024 _chemical_absolute_configuration ad _chemical_formula_moiety '2(Cl O4), H2 O, C6 H9 N3 O' _chemical_formula_sum 'C6 H11 Cl2 N3 O10' _chemical_formula_weight 356.08 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2024-01-11 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _audit_update_record ; 2024-01-20 deposited with the CCDC. 2024-03-25 downloaded from the CCDC. ; _cell_angle_alpha 90.00 _cell_angle_beta 94.788(16) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 4.9151(6) _cell_length_b 10.5757(16) _cell_length_c 12.470(3) _cell_measurement_reflns_used 1546 _cell_measurement_temperature 115.45(10) _cell_measurement_theta_max 26.1740 _cell_measurement_theta_min 3.7990 _cell_volume 645.9(2) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 115.45(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0971 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.6286 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -45.00 45.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 15.9289 -19.0000 60.0000 90 #__ type_ start__ end____ width___ exp.time_ 2 omega -12.00 27.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -10.8508 -99.0000 -120.0000 39 #__ type_ start__ end____ width___ exp.time_ 3 omega -53.00 -27.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 15.9289 -37.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 4 omega -7.00 27.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 15.9289 -37.0000 -180.0000 34 #__ type_ start__ end____ width___ exp.time_ 5 omega 41.00 88.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 15.9289 178.0000 150.0000 47 #__ type_ start__ end____ width___ exp.time_ 6 omega -2.00 70.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 15.9289 37.0000 -90.0000 72 #__ type_ start__ end____ width___ exp.time_ 7 omega -12.00 40.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 15.9289 19.0000 -120.0000 52 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0005425000 _diffrn_orient_matrix_UB_12 0.0593187000 _diffrn_orient_matrix_UB_13 -0.0267753000 _diffrn_orient_matrix_UB_21 -0.0545521000 _diffrn_orient_matrix_UB_22 -0.0292767000 _diffrn_orient_matrix_UB_23 -0.0483675000 _diffrn_orient_matrix_UB_31 -0.1344372000 _diffrn_orient_matrix_UB_32 0.0116122000 _diffrn_orient_matrix_UB_33 0.0146129000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_unetI/netI 0.0737 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 3462 _diffrn_reflns_theta_full 25.99 _diffrn_reflns_theta_max 25.99 _diffrn_reflns_theta_min 3.28 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.562 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92710 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.831 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 364 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _refine_diff_density_max 0.371 _refine_diff_density_min -0.485 _refine_diff_density_rms 0.072 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.49(8) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 198 _refine_ls_number_reflns 3462 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 0.990 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0424 _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^)+(0.0510P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0948 _refine_ls_wR_factor_ref 0.0969 _reflns_number_gt 3044 _reflns_number_total 3462 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d4nj01095g2.cif _cod_data_source_block exp_8898_twin1_hklf5 _cod_original_cell_volume 645.93(19) _cod_database_code 7063113 _diffrn_oxdiff_twin_integration_method simultaneous loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, 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 -0.3811(2) -1.09885(10) -0.55665(9) 0.0219(3) Uani 1 1 d . . . O4 O -0.2388(7) -1.1987(3) -0.6119(3) 0.0394(10) Uani 1 1 d . . . O5 O -0.5112(6) -1.0183(3) -0.6370(3) 0.0267(8) Uani 1 1 d . . . O2 O -0.1757(6) -1.0334(3) -0.4912(3) 0.0376(9) Uani 1 1 d . . . O10 O -0.0237(7) -0.8117(3) -0.5998(2) 0.0205(7) Uani 1 1 d D . . O3 O -0.5705(6) -1.1563(4) -0.4939(3) 0.0394(10) Uani 1 1 d . . . Cl2 Cl -0.12540(18) -0.93177(10) -0.91053(8) 0.0145(2) Uani 1 1 d . . . O1 O -0.1995(5) -0.6031(3) -0.7599(2) 0.0216(7) Uani 1 1 d . . . O7 O -0.4132(5) -0.9320(3) -0.8917(2) 0.0178(6) Uani 1 1 d . . . N3 N -0.5703(7) -0.7763(3) -0.7140(3) 0.0150(8) Uani 1 1 d . . . H3A H -0.6913 -0.8045 -0.6681 0.018 Uiso 1 1 calc R . . H3B H -0.3994 -0.7756 -0.6798 0.018 Uiso 1 1 calc R . . H3C H -0.5737 -0.8284 -0.7722 0.018 Uiso 1 1 calc R . . O9 O -0.0512(6) -0.8082(3) -0.9441(3) 0.0242(8) Uani 1 1 d . . . C6 C -0.7246(8) -0.3747(4) -0.7379(4) 0.0161(10) Uani 1 1 d . . . H6 H -0.8238 -0.4173 -0.6866 0.019 Uiso 1 1 calc R . . N1 N -0.6338(7) -0.1918(3) -0.8350(3) 0.0187(9) Uani 1 1 d . . . H1 H -0.6678 -0.1114 -0.8485 0.022 Uiso 1 1 calc R . . C1 C -0.4408(8) -0.5722(4) -0.7655(3) 0.0148(10) Uani 1 1 d . . . C5 C -0.7753(9) -0.2494(4) -0.7620(4) 0.0178(11) Uani 1 1 d . . . H5 H -0.9097 -0.2042 -0.7271 0.021 Uiso 1 1 calc R . . C3 C -0.3843(8) -0.3733(4) -0.8673(3) 0.0146(10) Uani 1 1 d . . . H3 H -0.2491 -0.4156 -0.9041 0.018 Uiso 1 1 calc R . . N2 N -0.6427(7) -0.6522(3) -0.7483(3) 0.0167(9) Uani 1 1 d . . . H2 H -0.8147 -0.6286 -0.7580 0.020 Uiso 1 1 calc R . . O6 O 0.0315(5) -0.9674(3) -0.8124(2) 0.0221(8) Uani 1 1 d . . . O8 O -0.0792(5) -1.0225(3) -0.9929(2) 0.0204(7) Uani 1 1 d . . . C2 C -0.5246(7) -0.4381(4) -0.7904(3) 0.0125(8) Uani 1 1 d . . . C4 C -0.4439(9) -0.2487(4) -0.8889(4) 0.0181(11) Uani 1 1 d . . . H4 H -0.3521 -0.2036 -0.9411 0.022 Uiso 1 1 calc R . . H10A H -0.007(10) -0.760(3) -0.548(2) 0.027 Uiso 1 1 d D . . H10B H -0.053(9) -0.8845(18) -0.574(3) 0.027 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0235(6) 0.0230(6) 0.0186(6) 0.0064(6) -0.0020(5) -0.0051(5) O4 0.043(2) 0.030(2) 0.047(3) -0.0020(19) 0.011(2) 0.0191(19) O5 0.0364(18) 0.0197(17) 0.0223(18) 0.0063(15) -0.0073(16) 0.0026(16) O2 0.0299(18) 0.049(2) 0.032(2) 0.0091(18) -0.0105(17) -0.0143(18) O10 0.0221(16) 0.0197(17) 0.0204(18) -0.0047(15) 0.0062(16) -0.0091(17) O3 0.019(2) 0.064(3) 0.035(2) 0.024(2) 0.0037(17) -0.0062(17) Cl2 0.0136(5) 0.0141(5) 0.0163(5) 0.0021(5) 0.0038(5) 0.0000(5) O1 0.0119(15) 0.0203(16) 0.0332(18) 0.0062(18) 0.0054(15) 0.0031(15) O7 0.0087(11) 0.0227(15) 0.0219(17) -0.0019(16) 0.0012(13) -0.0017(16) N3 0.0137(17) 0.0088(19) 0.023(2) 0.0007(16) 0.0020(17) -0.0008(16) O9 0.0247(17) 0.0156(17) 0.033(2) 0.0051(15) 0.0059(15) -0.0018(15) C6 0.013(2) 0.018(2) 0.018(3) 0.001(2) 0.0032(19) -0.004(2) N1 0.0157(19) 0.013(2) 0.026(2) 0.0008(18) -0.0039(19) 0.0018(17) C1 0.018(2) 0.019(3) 0.009(2) 0.0001(18) 0.005(2) -0.002(2) C5 0.017(2) 0.017(2) 0.019(3) -0.003(2) 0.003(2) -0.002(2) C3 0.015(2) 0.017(2) 0.012(2) -0.002(2) 0.0040(19) 0.004(2) N2 0.013(2) 0.0128(19) 0.025(2) 0.0024(16) 0.0045(16) -0.0038(16) O6 0.0157(14) 0.029(2) 0.0210(18) 0.0023(15) -0.0007(14) 0.0025(14) O8 0.0228(16) 0.0213(17) 0.0188(17) -0.0065(14) 0.0116(14) 0.0003(15) C2 0.0124(18) 0.009(2) 0.016(2) -0.002(2) -0.0002(17) -0.003(2) C4 0.021(2) 0.018(3) 0.015(2) 0.003(2) 0.001(2) -0.003(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 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' Cl Cl 0.1484 0.1585 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Cl1 O4 107.7(2) . . ? O2 Cl1 O4 106.0(2) . . ? O2 Cl1 O5 111.6(2) . . ? O3 Cl1 O4 108.3(2) . . ? O3 Cl1 O5 111.76(19) . . ? O3 Cl1 O2 111.3(2) . . ? H10A O10 H10B 108(2) . . ? O9 Cl2 O7 108.93(18) . . ? O9 Cl2 O6 110.86(18) . . ? O9 Cl2 O8 110.0(2) . . ? O6 Cl2 O7 108.76(16) . . ? O8 Cl2 O7 109.18(18) . . ? O8 Cl2 O6 109.12(18) . . ? H3A N3 H3B 109.5 . . ? H3A N3 H3C 109.5 . . ? H3B N3 H3C 109.5 . . ? N2 N3 H3A 109.5 . . ? N2 N3 H3B 109.5 . . ? N2 N3 H3C 109.5 . . ? C5 C6 H6 120.6 . . ? C5 C6 C2 118.8(4) . . ? C2 C6 H6 120.6 . . ? C5 N1 H1 117.9 . . ? C5 N1 C4 124.2(4) . . ? C4 N1 H1 117.9 . . ? O1 C1 N2 123.4(4) . . ? O1 C1 C2 120.7(4) . . ? N2 C1 C2 115.9(3) . . ? C6 C5 H5 120.3 . . ? N1 C5 C6 119.4(4) . . ? N1 C5 H5 120.3 . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C4 C3 C2 119.5(4) . . ? N3 N2 H2 121.2 . . ? C1 N2 N3 117.7(3) . . ? C1 N2 H2 121.2 . . ? C6 C2 C1 123.2(4) . . ? C6 C2 C3 119.4(4) . . ? C3 C2 C1 117.3(4) . . ? N1 C4 C3 118.7(4) . . ? N1 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 O4 1.469(3) . ? Cl1 O5 1.425(3) . ? Cl1 O2 1.424(3) . ? Cl1 O3 1.404(3) . ? O10 H10A 0.847(10) . ? O10 H10B 0.852(10) . ? Cl2 O7 1.453(3) . ? Cl2 O9 1.428(3) . ? Cl2 O6 1.441(3) . ? Cl2 O8 1.438(3) . ? O1 C1 1.227(5) . ? N3 H3A 0.9100 . ? N3 H3B 0.9100 . ? N3 H3C 0.9100 . ? N3 N2 1.417(5) . ? C6 H6 0.9500 . ? C6 C5 1.378(6) . ? C6 C2 1.396(6) . ? N1 H1 0.8800 . ? N1 C5 1.337(6) . ? N1 C4 1.337(6) . ? C1 N2 1.335(5) . ? C1 C2 1.501(6) . ? C5 H5 0.9500 . ? C3 H3 0.9500 . ? C3 C2 1.406(6) . ? C3 C4 1.373(6) . ? N2 H2 0.8800 . ? C4 H4 0.9500 . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 N2 N3 4.9(6) . . . . ? O1 C1 C2 C6 -138.2(4) . . . . ? O1 C1 C2 C3 39.0(5) . . . . ? C5 C6 C2 C1 176.1(4) . . . . ? C5 C6 C2 C3 -1.1(6) . . . . ? C5 N1 C4 C3 -1.3(6) . . . . ? N2 C1 C2 C6 40.5(6) . . . . ? N2 C1 C2 C3 -142.2(4) . . . . ? C2 C6 C5 N1 0.3(6) . . . . ? C2 C1 N2 N3 -173.8(3) . . . . ? C2 C3 C4 N1 0.5(6) . . . . ? C4 N1 C5 C6 0.9(6) . . . . ? C4 C3 C2 C6 0.6(6) . . . . ? C4 C3 C2 C1 -176.7(4) . . . . ? loop_ _diffrn_oxdiff_twin_id _diffrn_oxdiff_twin_ratio _diffrn_oxdiff_twin_reflns_isolated _diffrn_oxdiff_twin_reflns_overlapped 1 0.5310 1381 3460 2 0.4690 1355 3460