#------------------------------------------------------------------------------ #$Date: 2016-09-10 02:30:30 +0300 (Sat, 10 Sep 2016) $ #$Revision: 186393 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/03/99/7039954.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_7039954 loop_ _publ_author_name 'Voitekhovich, Sergei V.' 'Grigoriev, Yuri V.' 'Lyakhov, Alexander S.' 'Ivashkevich, Ludmila S.' 'Ivashkevich, Oleg A.' _publ_section_title ; The first organocopper tetrazole derivative: synthesis and characterization. ; _journal_issue 34 _journal_name_full 'Dalton transactions (Cambridge, England : 2003)' _journal_page_first 13406 _journal_page_last 13414 _journal_paper_doi 10.1039/c6dt02306a _journal_volume 45 _journal_year 2016 _chemical_formula_moiety 'C5 H14 N6, 2(Cl)' _chemical_formula_sum 'C5 H14 Cl2 N6' _chemical_formula_weight 229.12 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2016-06-08 deposited with the CCDC. 2016-07-20 downloaded from the CCDC. ; _cell_angle_alpha 74.7992(14) _cell_angle_beta 79.8889(14) _cell_angle_gamma 89.0669(15) _cell_formula_units_Z 2 _cell_length_a 7.4185(10) _cell_length_b 7.9458(10) _cell_length_c 9.3820(12) _cell_measurement_reflns_used 2338 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 28.06 _cell_measurement_theta_min 2.29 _cell_volume 525.14(12) _computing_cell_refinement 'SAINT (Bruker, 2010)' _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_data_reduction 'SAINT (Bruker, 2010)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material ; SHELXL-2014/7 (Sheldrick, 2015), PLATON (Spek, 2009) ; _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2015)' _computing_structure_solution 'SIR2014 (Burla et al., 2015)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_unetI/netI 0.0216 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 4787 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.997 _diffrn_reflns_theta_min 2.286 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.586 _exptl_absorpt_correction_T_max 0.7458 _exptl_absorpt_correction_T_min 0.6860 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.449 _exptl_crystal_description lamina _exptl_crystal_F_000 240 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.193 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.037 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 2051 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.020 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0262 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0431P)^2^+0.0479P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0678 _refine_ls_wR_factor_ref 0.0718 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1746 _reflns_number_total 2051 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6dt02306a2.cif _cod_data_source_block I _cod_depositor_comments 'Adding full bibliography for 7039954--7039958.cif.' _cod_database_code 7039954 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.844 _shelx_estimated_absorpt_t_max 0.971 _shelx_res_file ; 01.res created by SHELXL-2014/7 TITL 01 in P-1 CELL 0.71073 7.4185 7.9458 9.3820 74.7992 79.8889 89.0669 ZERR 2.00 0.0010 0.0010 0.0012 0.0014 0.0014 0.0015 LATT 1 SFAC C H N CL UNIT 10 28 12 4 TEMP 23.000 SIZE 0.05 0.25 0.30 omit -3 52 eqiv $1 -x, -y, -z eqiv $2 -x+1, -y, -z+1 eqiv $3 -x, -y, -z+1 eqiv $4 x, y-1, z eqiv $5 x,y,-1+z eqiv $6 1-x,1-y,1-z acta conf bond $H L.S. 6 mpla 5 N1 > C5 C6 htab N8 N4_$1 htab N8 CL1 htab N11 CL2_$2 htab N11 CL1_$3 htab N11 CL2_$4 htab C5 CL2_$5 htab C7 CL2_$6 rem htab C6 CL2_$5 small DHA angle! WGHT 0.043100 0.047900 FVAR 0.38281 CL1 4 0.121708 0.225386 0.536639 11.00000 0.03164 0.04852 = 0.03784 -0.01756 -0.00298 0.00046 CL2 4 0.428086 0.466157 0.767459 11.00000 0.04611 0.03924 = 0.03619 -0.00841 -0.00172 -0.00432 rem Tz Dianion N1 3 0.012841 0.252570 0.052509 11.00000 0.03375 0.02937 = 0.02882 -0.00566 -0.00343 0.00457 N2 3 -0.148315 0.180035 0.135967 11.00000 0.04039 0.04725 = 0.03952 -0.00938 0.00657 0.00460 N3 3 -0.233299 0.125548 0.046835 11.00000 0.03399 0.05324 = 0.05368 -0.01304 0.00031 -0.00011 N4 3 -0.131293 0.160179 -0.093783 11.00000 0.03493 0.04165 = 0.04150 -0.01075 -0.00549 -0.00006 C5 1 0.019501 0.237361 -0.085987 11.00000 0.03437 0.03550 = 0.03050 -0.00582 -0.00207 -0.00184 H5 2 0.112780 0.274754 -0.158034 11.00000 0.03196 C6 1 0.149489 0.323853 0.118036 11.00000 0.05340 0.02927 = 0.03182 -0.00975 -0.00937 0.00255 H6A 2 0.198462 0.428599 0.048055 11.00000 0.03895 H6B 2 0.086401 0.348276 0.203425 11.00000 0.03541 C7 1 0.304946 0.203180 0.149602 11.00000 0.03785 0.03201 = 0.02995 -0.00504 -0.00503 -0.00498 H7A 2 0.353298 0.160387 0.065433 11.00000 0.03375 H7B 2 0.399039 0.267892 0.178280 11.00000 0.04720 N8 3 0.247661 0.046863 0.278297 11.00000 0.02849 0.03013 = 0.02810 -0.00794 -0.00574 -0.00151 H8A 2 0.165845 -0.017010 0.256297 11.00000 0.03761 H8B 2 0.199179 0.084897 0.359044 11.00000 0.04772 C9 1 0.408222 -0.060939 0.316114 11.00000 0.02601 0.03636 = 0.03631 -0.00944 -0.00359 0.00132 H9A 2 0.450288 -0.111102 0.241134 11.00000 0.03958 H9B 2 0.500998 0.019681 0.314761 11.00000 0.03979 C10 1 0.372142 -0.191801 0.466533 11.00000 0.03050 0.03829 = 0.03364 -0.00768 -0.00987 0.00320 H10A 2 0.489107 -0.225064 0.493183 11.00000 0.03497 H10B 2 0.299956 -0.145538 0.537471 11.00000 0.03812 N11 3 0.278459 -0.355073 0.467112 11.00000 0.03230 0.03528 = 0.04235 -0.00381 -0.00303 0.00091 H11A 2 0.341946 -0.397104 0.392988 11.00000 0.05238 H11B 2 0.156784 -0.342127 0.460939 11.00000 0.05182 H11C 2 0.285545 -0.431579 0.550982 11.00000 0.05119 HKLF 4 REM 01 in P-1 REM R1 = 0.0262 for 1746 Fo > 4sig(Fo) and 0.0345 for all 2051 data REM 174 parameters refined using 0 restraints END WGHT 0.0389 0.0622 REM Highest difference peak 0.193, deepest hole -0.176, 1-sigma level 0.037 Q1 1 0.1218 0.1150 0.5718 11.00000 0.05 0.19 Q2 1 0.2150 0.2487 0.1457 11.00000 0.05 0.19 Q3 1 0.0863 0.2748 0.0767 11.00000 0.05 0.18 Q4 1 -0.0003 0.2960 -0.0233 11.00000 0.05 0.17 Q5 1 -0.0663 0.2245 0.0868 11.00000 0.05 0.16 Q6 1 0.0539 0.2016 0.0062 11.00000 0.05 0.16 Q7 1 -0.1896 0.1529 -0.0410 11.00000 0.05 0.15 Q8 1 0.1008 0.2595 0.4457 11.00000 0.05 0.15 Q9 1 -0.2197 0.1904 0.0830 11.00000 0.05 0.15 Q10 1 0.3662 0.5609 0.7794 11.00000 0.05 0.14 Q11 1 0.3739 -0.1335 0.3846 11.00000 0.05 0.14 Q12 1 0.2814 0.1277 0.2156 11.00000 0.05 0.14 Q13 1 0.0005 0.2222 0.5043 11.00000 0.05 0.13 Q14 1 0.4079 0.4460 0.6819 11.00000 0.05 0.13 Q15 1 -0.1696 0.2024 -0.1629 11.00000 0.05 0.13 Q16 1 -0.3098 0.0776 0.0594 11.00000 0.05 0.12 Q17 1 0.5284 0.3879 0.7068 11.00000 0.05 0.12 Q18 1 -0.0396 0.1678 -0.0806 11.00000 0.05 0.12 Q19 1 0.1853 0.2201 0.6207 11.00000 0.05 0.12 Q20 1 0.0837 0.3012 0.6030 11.00000 0.05 0.11 ; _shelx_res_checksum 20209 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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_site_symmetry_order _atom_site_calc_flag Cl1 Cl 0.12171(5) 0.22539(6) 0.53664(5) 0.03854(13) Uani 1 1 d Cl2 Cl 0.42809(6) 0.46616(5) 0.76746(5) 0.04144(14) Uani 1 1 d N1 N 0.01284(17) 0.25257(17) 0.05251(14) 0.0313(3) Uani 1 1 d N2 N -0.14831(19) 0.1800(2) 0.13597(17) 0.0445(4) Uani 1 1 d N3 N -0.23330(19) 0.1255(2) 0.04684(19) 0.0482(4) Uani 1 1 d N4 N -0.13129(18) 0.16018(19) -0.09378(16) 0.0395(3) Uani 1 1 d C5 C 0.0195(2) 0.2374(2) -0.08599(19) 0.0344(4) Uani 1 1 d H5 H 0.113(2) 0.275(2) -0.1580(19) 0.032(4) Uiso 1 1 d C6 C 0.1495(3) 0.3239(2) 0.1180(2) 0.0376(4) Uani 1 1 d H6A H 0.198(2) 0.429(2) 0.048(2) 0.039(5) Uiso 1 1 d H6B H 0.086(2) 0.348(2) 0.203(2) 0.035(5) Uiso 1 1 d C7 C 0.3049(2) 0.2032(2) 0.14960(19) 0.0339(4) Uani 1 1 d H7A H 0.353(2) 0.160(2) 0.065(2) 0.034(4) Uiso 1 1 d H7B H 0.399(2) 0.268(2) 0.178(2) 0.047(5) Uiso 1 1 d N8 N 0.24766(17) 0.04686(17) 0.27830(15) 0.0287(3) Uani 1 1 d H8A H 0.166(2) -0.017(2) 0.2563(19) 0.038(5) Uiso 1 1 d H8B H 0.199(2) 0.085(3) 0.359(2) 0.048(5) Uiso 1 1 d C9 C 0.4082(2) -0.0609(2) 0.31611(19) 0.0332(4) Uani 1 1 d H9A H 0.450(2) -0.111(2) 0.241(2) 0.040(5) Uiso 1 1 d H9B H 0.501(2) 0.020(2) 0.315(2) 0.040(5) Uiso 1 1 d C10 C 0.3721(2) -0.1918(2) 0.46653(19) 0.0340(4) Uani 1 1 d H10A H 0.489(2) -0.225(2) 0.4932(18) 0.035(4) Uiso 1 1 d H10B H 0.300(2) -0.146(2) 0.537(2) 0.038(5) Uiso 1 1 d N11 N 0.2785(2) -0.35507(19) 0.46711(19) 0.0383(3) Uani 1 1 d H11A H 0.342(3) -0.397(3) 0.393(2) 0.052(6) Uiso 1 1 d H11B H 0.157(3) -0.342(3) 0.461(2) 0.052(5) Uiso 1 1 d H11C H 0.286(3) -0.432(3) 0.551(2) 0.051(6) Uiso 1 1 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 0.0316(2) 0.0485(3) 0.0378(2) -0.01756(18) -0.00298(16) 0.00046(17) Cl2 0.0461(2) 0.0392(2) 0.0362(2) -0.00841(18) -0.00172(18) -0.00432(18) N1 0.0337(7) 0.0294(7) 0.0288(7) -0.0057(5) -0.0034(5) 0.0046(5) N2 0.0404(8) 0.0472(9) 0.0395(8) -0.0094(7) 0.0066(6) 0.0046(7) N3 0.0340(7) 0.0532(9) 0.0537(10) -0.0130(8) 0.0003(7) -0.0001(7) N4 0.0349(7) 0.0417(8) 0.0415(8) -0.0108(6) -0.0055(6) -0.0001(6) C5 0.0344(8) 0.0355(9) 0.0305(9) -0.0058(7) -0.0021(7) -0.0018(7) C6 0.0534(10) 0.0293(9) 0.0318(9) -0.0098(7) -0.0094(8) 0.0026(8) C7 0.0379(8) 0.0320(9) 0.0300(9) -0.0050(7) -0.0050(7) -0.0050(7) N8 0.0285(6) 0.0301(7) 0.0281(7) -0.0079(6) -0.0057(5) -0.0015(5) C9 0.0260(8) 0.0364(9) 0.0363(9) -0.0094(7) -0.0036(6) 0.0013(7) C10 0.0305(8) 0.0383(9) 0.0336(9) -0.0077(7) -0.0099(7) 0.0032(7) N11 0.0323(8) 0.0353(8) 0.0423(9) -0.0038(7) -0.0030(7) 0.0009(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 C5 N1 N2 107.94(13) C5 N1 C6 130.23(14) N2 N1 C6 121.77(14) N3 N2 N1 106.25(13) N2 N3 N4 110.75(13) C5 N4 N3 105.48(14) N4 C5 N1 109.57(15) N4 C5 H5 127.4(11) N1 C5 H5 123.0(11) N1 C6 C7 113.19(14) N1 C6 H6A 107.3(10) C7 C6 H6A 108.3(10) N1 C6 H6B 105.9(10) C7 C6 H6B 112.3(10) H6A C6 H6B 109.7(15) N8 C7 C6 112.56(14) N8 C7 H7A 106.5(10) C6 C7 H7A 111.5(10) N8 C7 H7B 106.8(11) C6 C7 H7B 107.7(11) H7A C7 H7B 111.8(14) C7 N8 C9 111.19(12) C7 N8 H8A 109.9(11) C9 N8 H8A 109.7(11) C7 N8 H8B 107.9(12) C9 N8 H8B 107.8(11) H8A N8 H8B 110.3(16) N8 C9 C10 114.24(13) N8 C9 H9A 109.2(11) C10 C9 H9A 112.1(11) N8 C9 H9B 105.3(10) C10 C9 H9B 109.4(11) H9A C9 H9B 106.0(16) N11 C10 C9 114.08(14) N11 C10 H10A 105.9(10) C9 C10 H10A 106.9(10) N11 C10 H10B 107.0(11) C9 C10 H10B 111.0(11) H10A C10 H10B 111.9(15) C10 N11 H11A 108.2(13) C10 N11 H11B 113.3(13) H11A N11 H11B 112.8(18) C10 N11 H11C 108.0(13) H11A N11 H11C 106.5(19) H11B N11 H11C 107.6(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C5 1.329(2) N1 N2 1.3534(18) N1 C6 1.465(2) N2 N3 1.292(2) N3 N4 1.362(2) N4 C5 1.307(2) C5 H5 0.872(17) C6 C7 1.507(2) C6 H6A 0.946(19) C6 H6B 0.919(18) C7 N8 1.494(2) C7 H7A 0.951(17) C7 H7B 0.987(19) N8 C9 1.495(2) N8 H8A 0.882(18) N8 H8B 0.90(2) C9 C10 1.500(2) C9 H9A 0.904(19) C9 H9B 0.944(18) C10 N11 1.480(2) C10 H10A 0.959(17) C10 H10B 0.928(19) N11 H11A 0.90(2) N11 H11B 0.92(2) N11 H11C 0.87(2) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N8 H8A N4 0.882(18) 2.177(19) 2.918(2) 141.2(15) 2 N8 H8B Cl1 0.90(2) 2.23(2) 3.1184(15) 168.0(17) . N11 H11A Cl2 0.90(2) 2.23(2) 3.1041(17) 161.9(17) 2_656 N11 H11B Cl1 0.92(2) 2.25(2) 3.1295(16) 160.6(17) 2_556 N11 H11C Cl2 0.87(2) 2.40(2) 3.1840(18) 150.2(17) 1_545 C5 H5 Cl2 0.872(17) 2.694(17) 3.4334(17) 143.3(14) 1_554 C7 H7B Cl2 0.987(19) 2.69(2) 3.6351(18) 159.8(14) 2_666 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 C5 N1 N2 N3 -0.53(17) C6 N1 N2 N3 -177.89(14) N1 N2 N3 N4 0.17(18) N2 N3 N4 C5 0.25(19) N3 N4 C5 N1 -0.58(18) N2 N1 C5 N4 0.71(18) C6 N1 C5 N4 177.76(15) C5 N1 C6 C7 -75.5(2) N2 N1 C6 C7 101.17(18) N1 C6 C7 N8 -71.19(19) C6 C7 N8 C9 -174.49(14) C7 N8 C9 C10 164.72(14) N8 C9 C10 N11 81.73(19)