#------------------------------------------------------------------------------ #$Date: 2024-01-06 10:05:58 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288809 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247624.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_7247624 loop_ _publ_author_name 'Wood, Oskar G.' 'Jones, Leanne' 'Hawes, Chris S.' _publ_section_title ; Supporting coordination through hydrogen bonding in lanthanide complexes of 7-azaindole-N-oxide ; _journal_issue 45 _journal_name_full CrystEngComm _journal_page_first 6371 _journal_page_last 6378 _journal_paper_doi 10.1039/D3CE00985H _journal_volume 25 _journal_year 2023 _chemical_formula_moiety 'C14 H10 Cu N4 O2' _chemical_formula_sum 'C14 H10 Cu N4 O2' _chemical_formula_weight 329.80 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2023-08-02 _audit_creation_method ; Olex2 1.5 (compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748) ; _audit_update_record ; 2023-08-10 deposited with the CCDC. 2023-11-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.867(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.6982(5) _cell_length_b 11.0452(6) _cell_length_c 13.7542(8) _cell_measurement_reflns_used 4840 _cell_measurement_temperature 150.00 _cell_measurement_theta_max 27.477 _cell_measurement_theta_min 3.064 _cell_volume 1264.57(12) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 150.00 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker D8 Quest ECO' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_unetI/netI 0.0495 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 15000 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.534 _diffrn_reflns_theta_min 3.064 _diffrn_source_current 20.0 _diffrn_source_power 1.0 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.737 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6447 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0683 before and 0.0585 after correction. The Ratio of minimum to maximum transmission is 0.8647. The \l/2 correction factor is Not present. ; _exptl_crystal_colour green _exptl_crystal_colour_primary green _exptl_crystal_density_diffrn 1.732 _exptl_crystal_description plate _exptl_crystal_F_000 668 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.568 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.087 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 2911 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.0684 _refine_ls_R_factor_gt 0.0403 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0339P)^2^+1.2299P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0788 _refine_ls_wR_factor_ref 0.0892 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2173 _reflns_number_total 2911 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00985h2.cif _cod_data_source_block 1 _cod_depositor_comments 'Adding full bibliography for 7247622--7247628.cif.' _cod_database_code 7247624 _shelx_shelxl_version_number 2018/3 _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_max 0.966 _shelx_estimated_absorpt_t_min 0.745 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14) ; _shelx_res_file ; TITL ow5f_green_0m_a.res in P2(1)/n ow5f_green_0m.res created by SHELXL-2018/3 at 15:49:19 on 22-Jul-2022 REM Old TITL OW5F_Green_0m in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.106, Rweak 0.005, Alpha 0.029, Orientation as input REM Formula found by SHELXT: C15 N3 O2 Cu CELL 0.71073 8.6982 11.0452 13.7542 90 106.867 90 ZERR 4 0.0005 0.0006 0.0008 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Cu N O UNIT 56 40 4 16 8 L.S. 4 PLAN 5 SIZE 0.02 0.04 0.18 TEMP -123.15 CONF BOND $H list 4 MORE -1 fmap 2 ACTA OMIT 0 1 1 OMIT -1 0 1 REM REM REM WGHT 0.033900 1.229900 FVAR 0.42016 CU1 3 0.433607 0.386732 0.557148 11.00000 0.02296 0.01865 = 0.02696 0.00322 0.00869 0.00201 O1 5 0.538900 0.281498 0.675885 11.00000 0.03660 0.02740 = 0.03275 0.00388 0.01151 0.00263 O2 5 0.315877 0.486148 0.435872 11.00000 0.02676 0.02172 = 0.02767 0.00145 0.00772 0.00395 N1 4 0.502253 0.266370 0.478229 11.00000 0.02733 0.02009 = 0.03192 -0.00191 0.00944 0.00015 N2 4 0.607897 0.187616 0.642070 11.00000 0.02336 0.02395 = 0.03670 0.00465 0.00725 -0.00083 N3 4 0.329759 0.492595 0.630714 11.00000 0.02128 0.02929 = 0.02777 0.00254 0.00956 0.00172 N4 4 0.210497 0.558605 0.464366 11.00000 0.02074 0.02000 = 0.03414 0.00266 0.00722 -0.00125 C1 1 0.515612 0.232229 0.385518 11.00000 0.03068 0.02842 = 0.03411 -0.00273 0.00781 -0.00258 AFIX 43 H1 2 0.467465 0.274719 0.324173 11.00000 -1.20000 AFIX 0 C2 1 0.607466 0.128505 0.391281 11.00000 0.03267 0.03087 = 0.04244 -0.01231 0.01810 -0.00089 AFIX 43 H2 2 0.632736 0.088742 0.336613 11.00000 -1.20000 AFIX 0 C3 1 0.656038 0.093629 0.494413 11.00000 0.02561 0.02264 = 0.05310 -0.00372 0.01013 -0.00170 C4 1 0.588234 0.182193 0.542379 11.00000 0.01930 0.01736 = 0.03787 0.00117 0.00725 -0.00289 C5 1 0.748039 0.004730 0.557513 11.00000 0.03084 0.02421 = 0.06248 0.00448 0.01408 0.00546 AFIX 43 H5 2 0.798347 -0.057771 0.530350 11.00000 -1.20000 AFIX 0 C6 1 0.763906 0.009969 0.659726 11.00000 0.02563 0.02797 = 0.07401 0.01636 0.00454 0.00430 AFIX 43 H6 2 0.823887 -0.051515 0.702594 11.00000 -1.20000 AFIX 0 C7 1 0.695544 0.101907 0.703264 11.00000 0.02377 0.02935 = 0.04351 0.01685 0.00082 -0.00015 AFIX 43 H7 2 0.710534 0.103944 0.774466 11.00000 -1.20000 AFIX 0 C8 1 0.303589 0.520870 0.722208 11.00000 0.03238 0.04102 = 0.02852 -0.00045 0.01731 -0.00223 AFIX 43 H8 2 0.362755 0.487161 0.785560 11.00000 -1.20000 AFIX 0 C9 1 0.181558 0.603738 0.710849 11.00000 0.03477 0.03844 = 0.04587 -0.00826 0.02483 -0.00447 AFIX 43 H9 2 0.143436 0.636219 0.763503 11.00000 -1.20000 AFIX 0 C10 1 0.123617 0.631477 0.606516 11.00000 0.02503 0.02323 = 0.05514 -0.00331 0.02133 -0.00184 C11 1 0.221526 0.559620 0.563394 11.00000 0.01960 0.01895 = 0.03468 0.00224 0.00858 0.00009 C12 1 0.007937 0.701900 0.538593 11.00000 0.02460 0.02429 = 0.07652 0.00075 0.01925 0.00214 AFIX 43 H12 2 -0.063567 0.751144 0.562000 11.00000 -1.20000 AFIX 0 C13 1 -0.000960 0.698843 0.436406 11.00000 0.02341 0.02242 = 0.06964 0.01266 0.00487 0.00223 AFIX 43 H13 2 -0.079372 0.747211 0.390238 11.00000 -1.20000 AFIX 0 C14 1 0.100350 0.627813 0.399212 11.00000 0.02582 0.02402 = 0.03732 0.00902 -0.00055 -0.00061 AFIX 43 H14 2 0.092190 0.627963 0.328822 11.00000 -1.20000 AFIX 0 HKLF 4 REM ow5f_green_0m_a.res in P2(1)/n REM wR2 = 0.089208, GooF = S = 1.02886, Restrained GooF = 1.02886 for all data REM R1 = 0.040299 for 2173 Fo > 4sig(Fo) and 0.068425 for all 2911 data REM 190 parameters refined using 0 restraints END WGHT 0.0339 1.2298 REM Highest difference peak 0.568, deepest hole -0.402, 1-sigma level 0.087 Q1 1 0.5433 0.2690 0.6080 11.00000 0.05 0.57 Q2 1 0.6350 0.2146 0.7278 11.00000 0.05 0.48 Q3 1 0.4257 0.3326 0.4964 11.00000 0.05 0.46 Q4 1 0.7447 0.0200 0.4772 11.00000 0.05 0.45 Q5 1 0.4674 0.2866 0.4203 11.00000 0.05 0.41 ; _shelx_res_checksum 77562 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_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_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 _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.43361(4) 0.38673(3) 0.55715(3) 0.02255(12) Uani 1 1 d . . . . . O1 O 0.5389(3) 0.28150(19) 0.67588(17) 0.0319(5) Uani 1 1 d . . . . . O2 O 0.3159(2) 0.48615(18) 0.43587(16) 0.0254(5) Uani 1 1 d . . . . . N1 N 0.5023(3) 0.2664(2) 0.4782(2) 0.0263(6) Uani 1 1 d . . . . . N2 N 0.6079(3) 0.1876(2) 0.6421(2) 0.0283(6) Uani 1 1 d . . . . . N3 N 0.3298(3) 0.4926(2) 0.6307(2) 0.0256(6) Uani 1 1 d . . . . . N4 N 0.2105(3) 0.5586(2) 0.4644(2) 0.0251(6) Uani 1 1 d . . . . . C1 C 0.5156(4) 0.2322(3) 0.3855(3) 0.0314(7) Uani 1 1 d . . . . . H1 H 0.467465 0.274719 0.324173 0.038 Uiso 1 1 calc R U . . . C2 C 0.6075(4) 0.1285(3) 0.3913(3) 0.0338(8) Uani 1 1 d . . . . . H2 H 0.632736 0.088742 0.336613 0.041 Uiso 1 1 calc R U . . . C3 C 0.6560(4) 0.0936(3) 0.4944(3) 0.0341(8) Uani 1 1 d . . . . . C4 C 0.5882(3) 0.1822(3) 0.5424(3) 0.0251(7) Uani 1 1 d . . . . . C5 C 0.7480(4) 0.0047(3) 0.5575(3) 0.0391(9) Uani 1 1 d . . . . . H5 H 0.798347 -0.057771 0.530350 0.047 Uiso 1 1 calc R U . . . C6 C 0.7639(4) 0.0100(3) 0.6597(3) 0.0446(10) Uani 1 1 d . . . . . H6 H 0.823887 -0.051515 0.702594 0.054 Uiso 1 1 calc R U . . . C7 C 0.6955(4) 0.1019(3) 0.7033(3) 0.0341(8) Uani 1 1 d . . . . . H7 H 0.710534 0.103944 0.774466 0.041 Uiso 1 1 calc R U . . . C8 C 0.3036(4) 0.5209(3) 0.7222(3) 0.0322(8) Uani 1 1 d . . . . . H8 H 0.362755 0.487161 0.785560 0.039 Uiso 1 1 calc R U . . . C9 C 0.1816(4) 0.6037(3) 0.7108(3) 0.0369(8) Uani 1 1 d . . . . . H9 H 0.143436 0.636219 0.763503 0.044 Uiso 1 1 calc R U . . . C10 C 0.1236(4) 0.6315(3) 0.6065(3) 0.0324(8) Uani 1 1 d . . . . . C11 C 0.2215(3) 0.5596(3) 0.5634(2) 0.0243(7) Uani 1 1 d . . . . . C12 C 0.0079(4) 0.7019(3) 0.5386(3) 0.0408(9) Uani 1 1 d . . . . . H12 H -0.063567 0.751144 0.562000 0.049 Uiso 1 1 calc R U . . . C13 C -0.0010(4) 0.6988(3) 0.4364(3) 0.0403(9) Uani 1 1 d . . . . . H13 H -0.079372 0.747211 0.390238 0.048 Uiso 1 1 calc R U . . . C14 C 0.1004(4) 0.6278(3) 0.3992(3) 0.0311(7) Uani 1 1 d . . . . . H14 H 0.092190 0.627963 0.328822 0.037 Uiso 1 1 calc R U . . . 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 Cu1 0.02296(19) 0.01865(18) 0.0270(2) 0.00322(17) 0.00869(15) 0.00201(15) O1 0.0366(12) 0.0274(11) 0.0327(13) 0.0039(10) 0.0115(11) 0.0026(10) O2 0.0268(11) 0.0217(10) 0.0277(12) 0.0014(9) 0.0077(9) 0.0039(8) N1 0.0273(13) 0.0201(12) 0.0319(16) -0.0019(11) 0.0094(12) 0.0002(10) N2 0.0234(13) 0.0239(13) 0.0367(17) 0.0046(12) 0.0073(12) -0.0008(10) N3 0.0213(12) 0.0293(14) 0.0278(15) 0.0025(12) 0.0096(11) 0.0017(11) N4 0.0207(12) 0.0200(12) 0.0341(16) 0.0027(12) 0.0072(11) -0.0013(10) C1 0.0307(17) 0.0284(17) 0.034(2) -0.0027(15) 0.0078(15) -0.0026(14) C2 0.0327(17) 0.0309(18) 0.042(2) -0.0123(16) 0.0181(16) -0.0009(14) C3 0.0256(16) 0.0226(16) 0.053(2) -0.0037(16) 0.0101(16) -0.0017(13) C4 0.0193(15) 0.0174(14) 0.038(2) 0.0012(13) 0.0072(14) -0.0029(11) C5 0.0308(18) 0.0242(17) 0.062(3) 0.0045(18) 0.0141(18) 0.0055(14) C6 0.0256(17) 0.0280(18) 0.074(3) 0.0164(19) 0.0045(18) 0.0043(14) C7 0.0238(16) 0.0294(17) 0.044(2) 0.0168(16) 0.0008(15) -0.0001(13) C8 0.0324(17) 0.0410(19) 0.0285(19) -0.0004(15) 0.0173(15) -0.0022(14) C9 0.0348(18) 0.0384(19) 0.046(2) -0.0083(18) 0.0248(17) -0.0045(15) C10 0.0250(16) 0.0232(16) 0.055(2) -0.0033(15) 0.0213(16) -0.0018(13) C11 0.0196(14) 0.0189(14) 0.0347(19) 0.0022(14) 0.0086(13) 0.0001(11) C12 0.0246(17) 0.0243(17) 0.077(3) 0.0008(18) 0.0192(19) 0.0021(13) C13 0.0234(16) 0.0224(16) 0.070(3) 0.0127(18) 0.0049(17) 0.0022(13) C14 0.0258(16) 0.0240(16) 0.037(2) 0.0090(14) -0.0005(14) -0.0006(13) 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' Cu Cu 0.3201 1.2651 '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 O1 Cu1 O2 176.54(8) . . ? N1 Cu1 O1 85.13(10) . . ? N1 Cu1 O2 94.37(10) . . ? N1 Cu1 N3 170.05(10) . . ? N3 Cu1 O1 95.57(10) . . ? N3 Cu1 O2 84.32(9) . . ? N2 O1 Cu1 108.08(17) . . ? N4 O2 Cu1 107.84(16) . . ? C1 N1 Cu1 147.6(2) . . ? C4 N1 Cu1 108.2(2) . . ? C4 N1 C1 103.8(2) . . ? C4 N2 O1 116.9(2) . . ? C4 N2 C7 119.5(3) . . ? C7 N2 O1 123.6(3) . . ? C8 N3 Cu1 147.3(2) . . ? C11 N3 Cu1 108.3(2) . . ? C11 N3 C8 103.7(3) . . ? C11 N4 O2 116.4(2) . . ? C11 N4 C14 120.1(3) . . ? C14 N4 O2 123.6(3) . . ? N1 C1 H1 123.9 . . ? N1 C1 C2 112.2(3) . . ? C2 C1 H1 123.9 . . ? C1 C2 H2 126.8 . . ? C1 C2 C3 106.4(3) . . ? C3 C2 H2 126.8 . . ? C4 C3 C2 103.8(3) . . ? C5 C3 C2 140.0(3) . . ? C5 C3 C4 116.2(3) . . ? N1 C4 C3 113.7(3) . . ? N2 C4 N1 121.5(3) . . ? N2 C4 C3 124.7(3) . . ? C3 C5 H5 120.8 . . ? C6 C5 C3 118.4(3) . . ? C6 C5 H5 120.8 . . ? C5 C6 H6 118.6 . . ? C5 C6 C7 122.7(3) . . ? C7 C6 H6 118.6 . . ? N2 C7 C6 118.5(3) . . ? N2 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? N3 C8 H8 124.0 . . ? C9 C8 N3 111.9(3) . . ? C9 C8 H8 124.0 . . ? C8 C9 H9 126.4 . . ? C8 C9 C10 107.2(3) . . ? C10 C9 H9 126.4 . . ? C9 C10 C11 102.9(3) . . ? C12 C10 C9 141.1(3) . . ? C12 C10 C11 115.9(3) . . ? N3 C11 N4 121.9(3) . . ? N3 C11 C10 114.2(3) . . ? N4 C11 C10 123.9(3) . . ? C10 C12 H12 120.6 . . ? C13 C12 C10 118.9(3) . . ? C13 C12 H12 120.6 . . ? C12 C13 H13 118.8 . . ? C14 C13 C12 122.3(3) . . ? C14 C13 H13 118.8 . . ? N4 C14 C13 118.9(3) . . ? N4 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? 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 Cu1 O1 1.997(2) . ? Cu1 O2 2.011(2) . ? Cu1 N1 1.918(2) . ? Cu1 N3 1.933(2) . ? O1 N2 1.347(3) . ? O2 N4 1.357(3) . ? N1 C1 1.367(4) . ? N1 C4 1.349(4) . ? N2 C4 1.333(4) . ? N2 C7 1.347(4) . ? N3 C8 1.378(4) . ? N3 C11 1.336(4) . ? N4 C11 1.337(4) . ? N4 C14 1.344(4) . ? C1 H1 0.9500 . ? C1 C2 1.386(4) . ? C2 H2 0.9500 . ? C2 C3 1.411(5) . ? C3 C4 1.402(4) . ? C3 C5 1.398(5) . ? C5 H5 0.9500 . ? C5 C6 1.373(5) . ? C6 H6 0.9500 . ? C6 C7 1.396(5) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C8 C9 1.376(4) . ? C9 H9 0.9500 . ? C9 C10 1.410(5) . ? C10 C11 1.414(4) . ? C10 C12 1.395(5) . ? C12 H12 0.9500 . ? C12 C13 1.385(5) . ? C13 H13 0.9500 . ? C13 C14 1.384(5) . ? C14 H14 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 Cu1 O1 N2 C4 -2.2(3) . . . . ? Cu1 O1 N2 C7 176.9(2) . . . . ? Cu1 O2 N4 C11 7.9(3) . . . . ? Cu1 O2 N4 C14 -172.8(2) . . . . ? Cu1 N1 C1 C2 171.0(3) . . . . ? Cu1 N1 C4 N2 2.9(3) . . . . ? Cu1 N1 C4 C3 -175.4(2) . . . . ? Cu1 N3 C8 C9 -168.2(3) . . . . ? Cu1 N3 C11 N4 -7.8(3) . . . . ? Cu1 N3 C11 C10 173.1(2) . . . . ? O1 N2 C4 N1 -0.5(4) . . . . ? O1 N2 C4 C3 177.6(3) . . . . ? O1 N2 C7 C6 -178.8(3) . . . . ? O2 N4 C11 N3 -0.3(4) . . . . ? O2 N4 C11 C10 178.7(2) . . . . ? O2 N4 C14 C13 -179.7(3) . . . . ? N1 C1 C2 C3 0.1(4) . . . . ? N3 C8 C9 C10 0.2(4) . . . . ? C1 N1 C4 N2 177.7(3) . . . . ? C1 N1 C4 C3 -0.5(3) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C1 C2 C3 C5 -178.6(4) . . . . ? C2 C3 C4 N1 0.6(3) . . . . ? C2 C3 C4 N2 -177.6(3) . . . . ? C2 C3 C5 C6 178.5(4) . . . . ? C3 C5 C6 C7 -1.7(5) . . . . ? C4 N1 C1 C2 0.3(3) . . . . ? C4 N2 C7 C6 0.3(4) . . . . ? C4 C3 C5 C6 0.5(4) . . . . ? C5 C3 C4 N1 179.3(3) . . . . ? C5 C3 C4 N2 1.1(4) . . . . ? C5 C6 C7 N2 1.3(5) . . . . ? C7 N2 C4 N1 -179.6(3) . . . . ? C7 N2 C4 C3 -1.5(4) . . . . ? C8 N3 C11 N4 179.0(3) . . . . ? C8 N3 C11 C10 -0.2(3) . . . . ? C8 C9 C10 C11 -0.3(3) . . . . ? C8 C9 C10 C12 179.2(4) . . . . ? C9 C10 C11 N3 0.3(3) . . . . ? C9 C10 C11 N4 -178.8(3) . . . . ? C9 C10 C12 C13 179.2(4) . . . . ? C10 C12 C13 C14 0.4(5) . . . . ? C11 N3 C8 C9 0.0(3) . . . . ? C11 N4 C14 C13 -0.4(4) . . . . ? C11 C10 C12 C13 -1.3(4) . . . . ? C12 C10 C11 N3 -179.4(3) . . . . ? C12 C10 C11 N4 1.5(4) . . . . ? C12 C13 C14 N4 0.5(5) . . . . ? C14 N4 C11 N3 -179.7(3) . . . . ? C14 N4 C11 C10 -0.7(4) . . . . ?