#------------------------------------------------------------------------------ #$Date: 2023-11-02 01:37:20 +0200 (Thu, 02 Nov 2023) $ #$Revision: 287227 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247628.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_7247628 loop_ _publ_author_name 'Wood, Oskar G.' 'Jones, Leanne' 'Hawes, Chris Samuel' _publ_section_title ; Supporting coordination through hydrogen bonding in lanthanide complexes of 7-azaindole-N-oxide ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00985H _journal_year 2023 _chemical_formula_moiety 'C16 H16 Cu2 N4 O4' _chemical_formula_sum 'C16 H16 Cu2 N4 O4' _chemical_formula_weight 455.41 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 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 104.761(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.4309(6) _cell_length_b 10.4129(5) _cell_length_c 13.1342(6) _cell_measurement_reflns_used 5121 _cell_measurement_temperature 150.00 _cell_measurement_theta_max 28.256 _cell_measurement_theta_min 2.530 _cell_volume 1644.00(14) _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 0.999 _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 0.1167 _diffrn_reflns_av_unetI/netI 0.0742 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 33543 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.285 _diffrn_reflns_theta_min 2.808 _diffrn_source_current 20.0 _diffrn_source_power 1.0 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.619 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6622 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0763 before and 0.0670 after correction. The Ratio of minimum to maximum transmission is 0.8880. The \l/2 correction factor is Not present. ; _exptl_crystal_colour blue _exptl_crystal_colour_primary blue _exptl_crystal_density_diffrn 1.840 _exptl_crystal_description block _exptl_crystal_F_000 920 _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.820 _refine_diff_density_min -0.586 _refine_diff_density_rms 0.127 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 237 _refine_ls_number_reflns 4084 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.102 _refine_ls_R_factor_all 0.1063 _refine_ls_R_factor_gt 0.0632 _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^)+(0.0302P)^2^+3.7936P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0991 _refine_ls_wR_factor_ref 0.1104 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2816 _reflns_number_total 4084 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00985h2.cif _cod_data_source_block Cu2L2OMe2 _cod_database_code 7247628 _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 0.949 _shelx_estimated_absorpt_t_min 0.859 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,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) 2.b Idealised Me refined as rotating group: C15(H15A,H15B,H15C), C16(H16A,H16B,H16C) ; _shelx_res_file ; TITL ow5f_blue_0m_a.res in P2(1)/c ow5f_blue_0m.res created by SHELXL-2018/3 at 15:06:12 on 02-Aug-2023 REM Old TITL OW5F_Blue_0m in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.111, Rweak 0.014, Alpha 0.053, Orientation as input REM Formula found by SHELXT: C18 N3 O3 Cu2 CELL 0.71073 12.4309 10.4129 13.1342 90 104.761 90 ZERR 4 0.0006 0.0005 0.0006 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cu N O UNIT 64 64 8 16 16 L.S. 4 PLAN 5 SIZE 0.02 0.05 0.06 TEMP -123.15 CONF CONN 12 1.2 $Cu BOND $H list 4 MORE -1 fmap 2 acta OMIT 0 1 1 OMIT 1 1 0 REM REM REM WGHT 0.030200 3.793600 FVAR 0.34201 CU1 3 0.549926 0.553042 0.706965 11.00000 0.01972 0.02175 = 0.02323 0.00179 0.00775 0.00113 CU2 3 0.385918 0.573317 0.496767 11.00000 0.01836 0.01719 = 0.02368 0.00310 0.00759 0.00028 O1 5 0.540080 0.480587 0.844411 11.00000 0.02605 0.04396 = 0.02490 0.00268 0.00445 -0.00296 O2 5 0.393677 0.661927 0.363142 11.00000 0.02220 0.02469 = 0.03528 0.00839 0.00575 -0.00216 O3 5 0.540765 0.615573 0.564979 11.00000 0.01748 0.01861 = 0.02395 0.00257 0.00612 -0.00325 O4 5 0.398565 0.518707 0.638542 11.00000 0.02225 0.02288 = 0.02406 0.00529 0.00945 -0.00323 N1 4 0.699326 0.602897 0.782763 11.00000 0.03020 0.01770 = 0.03250 -0.00337 0.01273 -0.00050 N2 4 0.638960 0.491507 0.912864 11.00000 0.02953 0.02588 = 0.03130 -0.00190 0.01049 0.00321 N3 4 0.225900 0.558249 0.427901 11.00000 0.02274 0.01787 = 0.03665 -0.00346 0.01430 -0.00197 N4 4 0.289232 0.681051 0.304679 11.00000 0.02238 0.01869 = 0.03430 0.00139 0.00924 0.00496 C1 1 0.799675 0.657194 0.780663 11.00000 0.03231 0.02317 = 0.04307 -0.00065 0.02043 -0.00192 AFIX 43 H1 2 0.812815 0.699807 0.721017 11.00000 -1.20000 AFIX 0 C2 1 0.878957 0.642881 0.874674 11.00000 0.01842 0.02842 = 0.05043 -0.00550 0.00750 -0.00272 AFIX 43 H2 2 0.953405 0.673383 0.890523 11.00000 -1.20000 AFIX 0 C3 1 0.828406 0.574020 0.943280 11.00000 0.03359 0.01706 = 0.03929 -0.00386 0.00770 0.00036 C4 1 0.718892 0.553108 0.879476 11.00000 0.03194 0.01735 = 0.02661 -0.00501 0.00974 0.00375 C5 1 0.852490 0.520310 1.042942 11.00000 0.03150 0.02846 = 0.03298 -0.00325 -0.00562 0.00339 AFIX 43 H5 2 0.925144 0.527144 1.088405 11.00000 -1.20000 AFIX 0 C6 1 0.769561 0.456619 1.075510 11.00000 0.04444 0.02984 = 0.03058 0.00004 0.00272 0.00022 AFIX 43 H6 2 0.786255 0.420873 1.144305 11.00000 -1.20000 AFIX 0 C7 1 0.662454 0.443070 1.010967 11.00000 0.03840 0.02492 = 0.02666 0.00071 0.00712 -0.00095 AFIX 43 H7 2 0.606687 0.400186 1.035870 11.00000 -1.20000 AFIX 0 C8 1 0.121480 0.521422 0.432645 11.00000 0.02815 0.02438 = 0.03774 -0.00680 0.01630 -0.00439 AFIX 43 H8 2 0.107331 0.468839 0.486905 11.00000 -1.20000 AFIX 0 C9 1 0.039554 0.568697 0.350556 11.00000 0.02525 0.03094 = 0.03573 -0.00487 0.01227 0.00045 AFIX 43 H9 2 -0.038228 0.555324 0.338981 11.00000 -1.20000 AFIX 0 C10 1 0.093242 0.641695 0.285908 11.00000 0.02430 0.02134 = 0.03257 -0.00494 0.00764 0.00339 C11 1 0.206962 0.629100 0.339915 11.00000 0.02198 0.01639 = 0.02034 -0.00244 0.00928 0.00448 C12 1 0.068064 0.713858 0.194913 11.00000 0.02310 0.02658 = 0.03482 -0.00367 -0.00370 0.00272 AFIX 43 H12 2 -0.006945 0.727997 0.156994 11.00000 -1.20000 AFIX 0 C13 1 0.155782 0.765402 0.160222 11.00000 0.03690 0.02657 = 0.03063 0.00499 -0.00349 0.00418 AFIX 43 H13 2 0.139614 0.813887 0.096867 11.00000 -1.20000 AFIX 0 C14 1 0.265997 0.748367 0.215027 11.00000 0.03059 0.01762 = 0.02592 0.00274 0.00733 -0.00186 AFIX 43 H14 2 0.324230 0.784070 0.189195 11.00000 -1.20000 AFIX 0 C15 1 0.595874 0.727443 0.543717 11.00000 0.03325 0.01903 = 0.03072 0.00444 0.01353 -0.00182 AFIX 137 H15A 2 0.567200 0.751334 0.469573 11.00000 -1.50000 H15B 2 0.675926 0.710662 0.558278 11.00000 -1.50000 H15C 2 0.582667 0.797821 0.588574 11.00000 -1.50000 AFIX 0 C16 1 0.332367 0.426539 0.672358 11.00000 0.03977 0.03521 = 0.03070 0.00512 0.02235 -0.00697 AFIX 137 H16A 2 0.294712 0.466493 0.721384 11.00000 -1.50000 H16B 2 0.379558 0.356086 0.707865 11.00000 -1.50000 H16C 2 0.276747 0.392875 0.611367 11.00000 -1.50000 AFIX 0 HKLF 4 REM ow5f_blue_0m_a.res in P2(1)/c REM wR2 = 0.110383, GooF = S = 1.10217, Restrained GooF = 1.10217 for all data REM R1 = 0.063241 for 2816 Fo > 4sig(Fo) and 0.106272 for all 4084 data REM 237 parameters refined using 0 restraints END WGHT 0.0302 3.8105 REM Highest difference peak 0.820, deepest hole -0.586, 1-sigma level 0.127 Q1 1 0.7189 0.6401 0.7369 11.00000 0.05 0.82 Q2 1 0.5643 0.5175 0.5276 11.00000 0.05 0.63 Q3 1 0.3531 0.4464 0.7830 11.00000 0.05 0.58 Q4 1 0.1576 0.5806 0.3907 11.00000 0.05 0.57 Q5 1 0.9221 0.5623 0.9828 11.00000 0.05 0.53 ; _shelx_res_checksum 3877 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 0.54993(5) 0.55304(5) 0.70696(4) 0.02115(16) Uani 1 1 d . . . . . Cu2 Cu 0.38592(5) 0.57332(5) 0.49677(4) 0.01934(15) Uani 1 1 d . . . . . O1 O 0.5401(3) 0.4806(3) 0.8444(3) 0.0320(8) Uani 1 1 d . . . . . O2 O 0.3937(3) 0.6619(3) 0.3631(3) 0.0277(8) Uani 1 1 d . . . . . O3 O 0.5408(3) 0.6156(3) 0.5650(2) 0.0199(7) Uani 1 1 d . . . . . O4 O 0.3986(3) 0.5187(3) 0.6385(2) 0.0224(7) Uani 1 1 d . . . . . N1 N 0.6993(3) 0.6029(4) 0.7828(3) 0.0259(9) Uani 1 1 d . . . . . N2 N 0.6390(4) 0.4915(4) 0.9129(3) 0.0284(10) Uani 1 1 d . . . . . N3 N 0.2259(3) 0.5582(4) 0.4279(3) 0.0245(9) Uani 1 1 d . . . . . N4 N 0.2892(3) 0.6811(4) 0.3047(3) 0.0248(9) Uani 1 1 d . . . . . C1 C 0.7997(4) 0.6572(5) 0.7807(4) 0.0309(12) Uani 1 1 d . . . . . H1 H 0.812815 0.699807 0.721017 0.037 Uiso 1 1 calc R U . . . C2 C 0.8790(4) 0.6429(5) 0.8747(4) 0.0327(13) Uani 1 1 d . . . . . H2 H 0.953405 0.673383 0.890523 0.039 Uiso 1 1 calc R U . . . C3 C 0.8284(4) 0.5740(5) 0.9433(4) 0.0303(12) Uani 1 1 d . . . . . C4 C 0.7189(4) 0.5531(4) 0.8795(4) 0.0249(11) Uani 1 1 d . . . . . C5 C 0.8525(5) 0.5203(5) 1.0429(4) 0.0335(13) Uani 1 1 d . . . . . H5 H 0.925144 0.527144 1.088405 0.040 Uiso 1 1 calc R U . . . C6 C 0.7696(5) 0.4566(5) 1.0755(4) 0.0362(13) Uani 1 1 d . . . . . H6 H 0.786255 0.420873 1.144305 0.043 Uiso 1 1 calc R U . . . C7 C 0.6625(5) 0.4431(5) 1.0110(4) 0.0302(11) Uani 1 1 d . . . . . H7 H 0.606687 0.400186 1.035870 0.036 Uiso 1 1 calc R U . . . C8 C 0.1215(4) 0.5214(5) 0.4326(4) 0.0287(12) Uani 1 1 d . . . . . H8 H 0.107331 0.468839 0.486905 0.034 Uiso 1 1 calc R U . . . C9 C 0.0396(4) 0.5687(5) 0.3506(4) 0.0298(11) Uani 1 1 d . . . . . H9 H -0.038228 0.555324 0.338981 0.036 Uiso 1 1 calc R U . . . C10 C 0.0932(4) 0.6417(4) 0.2859(4) 0.0260(11) Uani 1 1 d . . . . . C11 C 0.2070(4) 0.6291(4) 0.3399(4) 0.0189(10) Uani 1 1 d . . . . . C12 C 0.0681(4) 0.7139(5) 0.1949(4) 0.0302(12) Uani 1 1 d . . . . . H12 H -0.006945 0.727997 0.156994 0.036 Uiso 1 1 calc R U . . . C13 C 0.1558(5) 0.7654(5) 0.1602(4) 0.0336(13) Uani 1 1 d . . . . . H13 H 0.139614 0.813887 0.096867 0.040 Uiso 1 1 calc R U . . . C14 C 0.2660(4) 0.7484(4) 0.2150(4) 0.0247(11) Uani 1 1 d . . . . . H14 H 0.324230 0.784070 0.189195 0.030 Uiso 1 1 calc R U . . . C15 C 0.5959(4) 0.7274(4) 0.5437(4) 0.0267(11) Uani 1 1 d . . . . . H15A H 0.567200 0.751334 0.469573 0.040 Uiso 1 1 calc R U . . . H15B H 0.675926 0.710662 0.558278 0.040 Uiso 1 1 calc R U . . . H15C H 0.582667 0.797821 0.588574 0.040 Uiso 1 1 calc R U . . . C16 C 0.3324(5) 0.4265(5) 0.6724(4) 0.0328(12) Uani 1 1 d . . . . . H16A H 0.294712 0.466493 0.721384 0.049 Uiso 1 1 calc R U . . . H16B H 0.379558 0.356086 0.707865 0.049 Uiso 1 1 calc R U . . . H16C H 0.276747 0.392875 0.611367 0.049 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 0.0197(3) 0.0218(3) 0.0232(3) 0.0018(2) 0.0078(2) 0.0011(2) Cu2 0.0184(3) 0.0172(3) 0.0237(3) 0.0031(2) 0.0076(2) 0.0003(2) O1 0.026(2) 0.044(2) 0.025(2) 0.0027(16) 0.0044(16) -0.0030(17) O2 0.0222(19) 0.0247(18) 0.035(2) 0.0084(15) 0.0057(16) -0.0022(15) O3 0.0175(17) 0.0186(15) 0.0239(18) 0.0026(13) 0.0061(14) -0.0032(13) O4 0.0223(18) 0.0229(17) 0.0241(18) 0.0053(13) 0.0095(15) -0.0032(14) N1 0.030(3) 0.018(2) 0.033(2) -0.0034(17) 0.013(2) -0.0005(17) N2 0.030(3) 0.026(2) 0.031(2) -0.0019(18) 0.010(2) 0.0032(19) N3 0.023(2) 0.0179(19) 0.037(2) -0.0035(18) 0.0143(18) -0.0020(17) N4 0.022(2) 0.019(2) 0.034(2) 0.0014(17) 0.0092(19) 0.0050(17) C1 0.032(3) 0.023(3) 0.043(3) -0.001(2) 0.020(3) -0.002(2) C2 0.018(3) 0.028(3) 0.050(4) -0.006(2) 0.007(3) -0.003(2) C3 0.034(3) 0.017(2) 0.039(3) -0.004(2) 0.008(2) 0.000(2) C4 0.032(3) 0.017(2) 0.027(3) -0.005(2) 0.010(2) 0.004(2) C5 0.032(3) 0.028(3) 0.033(3) -0.003(2) -0.006(2) 0.003(2) C6 0.044(4) 0.030(3) 0.031(3) 0.000(2) 0.003(3) 0.000(3) C7 0.038(3) 0.025(3) 0.027(3) 0.001(2) 0.007(2) -0.001(2) C8 0.028(3) 0.024(2) 0.038(3) -0.007(2) 0.016(2) -0.004(2) C9 0.025(3) 0.031(3) 0.036(3) -0.005(2) 0.012(2) 0.000(2) C10 0.024(3) 0.021(2) 0.033(3) -0.005(2) 0.008(2) 0.003(2) C11 0.022(3) 0.016(2) 0.020(2) -0.0024(18) 0.009(2) 0.0045(19) C12 0.023(3) 0.027(3) 0.035(3) -0.004(2) -0.004(2) 0.003(2) C13 0.037(3) 0.027(3) 0.031(3) 0.005(2) -0.003(3) 0.004(2) C14 0.031(3) 0.018(2) 0.026(3) 0.0027(19) 0.007(2) -0.002(2) C15 0.033(3) 0.019(2) 0.031(3) 0.004(2) 0.014(2) -0.002(2) C16 0.040(3) 0.035(3) 0.031(3) 0.005(2) 0.022(3) -0.007(3) 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 O3 Cu1 O1 172.79(14) . . ? O4 Cu1 O1 94.32(14) . . ? O4 Cu1 O3 78.53(13) . . ? O4 Cu1 N1 174.36(15) . . ? N1 Cu1 O1 84.72(16) . . ? N1 Cu1 O3 102.49(15) . . ? O3 Cu2 O2 92.07(13) . . ? O3 Cu2 N3 171.54(15) . . ? O4 Cu2 O2 167.61(14) . . ? O4 Cu2 O3 78.11(13) . . ? O4 Cu2 N3 104.24(15) . . ? N3 Cu2 O2 84.43(15) . . ? N2 O1 Cu1 108.7(3) . . ? N4 O2 Cu2 108.2(3) . . ? Cu1 O3 Cu2 100.01(13) . . ? C15 O3 Cu1 123.4(3) . . ? C15 O3 Cu2 124.4(3) . . ? Cu1 O4 Cu2 103.30(14) . . ? C16 O4 Cu1 124.5(3) . . ? C16 O4 Cu2 126.8(3) . . ? C1 N1 Cu1 148.6(4) . . ? C4 N1 Cu1 107.6(3) . . ? C4 N1 C1 103.4(4) . . ? O1 N2 C4 116.9(4) . . ? O1 N2 C7 123.6(4) . . ? C7 N2 C4 119.5(5) . . ? C8 N3 Cu2 149.2(4) . . ? C11 N3 Cu2 106.7(3) . . ? C11 N3 C8 103.5(4) . . ? C11 N4 O2 117.0(4) . . ? C14 N4 O2 122.8(4) . . ? C14 N4 C11 120.2(4) . . ? N1 C1 H1 123.8 . . ? N1 C1 C2 112.5(5) . . ? C2 C1 H1 123.8 . . ? C1 C2 H2 126.5 . . ? C1 C2 C3 107.0(5) . . ? C3 C2 H2 126.5 . . ? C2 C3 C4 102.5(5) . . ? C5 C3 C2 141.4(5) . . ? C5 C3 C4 116.1(5) . . ? N1 C4 N2 121.6(5) . . ? N1 C4 C3 114.6(4) . . ? N2 C4 C3 123.8(5) . . ? C3 C5 H5 120.4 . . ? C6 C5 C3 119.2(5) . . ? C6 C5 H5 120.4 . . ? C5 C6 H6 118.9 . . ? C5 C6 C7 122.2(5) . . ? C7 C6 H6 118.9 . . ? N2 C7 C6 119.1(5) . . ? N2 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? N3 C8 H8 123.6 . . ? N3 C8 C9 112.7(5) . . ? C9 C8 H8 123.6 . . ? C8 C9 H9 126.5 . . ? C8 C9 C10 107.0(5) . . ? C10 C9 H9 126.5 . . ? C11 C10 C9 102.2(4) . . ? C12 C10 C9 140.3(5) . . ? C12 C10 C11 117.5(4) . . ? N3 C11 C10 114.6(4) . . ? N4 C11 N3 122.6(4) . . ? N4 C11 C10 122.8(4) . . ? C10 C12 H12 121.0 . . ? C10 C12 C13 118.0(5) . . ? C13 C12 H12 121.0 . . ? C12 C13 H13 118.9 . . ? C14 C13 C12 122.2(5) . . ? C14 C13 H13 118.9 . . ? N4 C14 C13 119.2(5) . . ? N4 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? O3 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? O3 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O4 C16 H16A 109.5 . . ? O4 C16 H16B 109.5 . . ? O4 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 1.989(3) . ? Cu1 O3 1.951(3) . ? Cu1 O4 1.901(3) . ? Cu1 N1 1.941(4) . ? Cu2 O2 2.007(3) . ? Cu2 O3 1.955(3) . ? Cu2 O4 1.915(3) . ? Cu2 N3 1.970(4) . ? O1 N2 1.330(5) . ? O2 N4 1.344(5) . ? O3 C15 1.415(5) . ? O4 C16 1.408(5) . ? N1 C1 1.376(6) . ? N1 C4 1.336(6) . ? N2 C4 1.347(6) . ? N2 C7 1.345(6) . ? N3 C8 1.370(6) . ? N3 C11 1.340(6) . ? N4 C11 1.339(6) . ? N4 C14 1.337(6) . ? C1 H1 0.9500 . ? C1 C2 1.378(7) . ? C2 H2 0.9500 . ? C2 C3 1.418(7) . ? C3 C4 1.422(7) . ? C3 C5 1.384(7) . ? C5 H5 0.9500 . ? C5 C6 1.382(7) . ? C6 H6 0.9500 . ? C6 C7 1.391(7) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C8 C9 1.372(7) . ? C9 H9 0.9500 . ? C9 C10 1.426(7) . ? C10 C11 1.417(6) . ? C10 C12 1.379(7) . ? C12 H12 0.9500 . ? C12 C13 1.392(7) . ? C13 H13 0.9500 . ? C13 C14 1.387(7) . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 4.0(5) . . . . ? Cu1 O1 N2 C7 -174.9(4) . . . . ? Cu1 N1 C1 C2 -171.7(5) . . . . ? Cu1 N1 C4 N2 -5.6(5) . . . . ? Cu1 N1 C4 C3 176.1(3) . . . . ? Cu2 O2 N4 C11 -6.2(4) . . . . ? Cu2 O2 N4 C14 173.8(3) . . . . ? Cu2 N3 C8 C9 167.3(5) . . . . ? Cu2 N3 C11 N4 8.5(5) . . . . ? Cu2 N3 C11 C10 -173.1(3) . . . . ? O1 N2 C4 N1 1.1(6) . . . . ? O1 N2 C4 C3 179.3(4) . . . . ? O1 N2 C7 C6 178.2(4) . . . . ? O2 N4 C11 N3 -1.6(6) . . . . ? O2 N4 C11 C10 -179.9(4) . . . . ? O2 N4 C14 C13 -179.0(4) . . . . ? N1 C1 C2 C3 0.4(6) . . . . ? N3 C8 C9 C10 0.4(6) . . . . ? C1 N1 C4 N2 179.4(4) . . . . ? C1 N1 C4 C3 1.1(5) . . . . ? C1 C2 C3 C4 0.2(5) . . . . ? C1 C2 C3 C5 176.3(6) . . . . ? C2 C3 C4 N1 -0.9(5) . . . . ? C2 C3 C4 N2 -179.1(4) . . . . ? C2 C3 C5 C6 -178.7(6) . . . . ? C3 C5 C6 C7 0.8(8) . . . . ? C4 N1 C1 C2 -0.9(5) . . . . ? C4 N2 C7 C6 -0.7(7) . . . . ? C4 C3 C5 C6 -3.0(7) . . . . ? C5 C3 C4 N1 -178.1(4) . . . . ? C5 C3 C4 N2 3.6(7) . . . . ? C5 C6 C7 N2 1.2(8) . . . . ? C7 N2 C4 N1 -179.9(4) . . . . ? C7 N2 C4 C3 -1.8(7) . . . . ? C8 N3 C11 N4 -178.0(4) . . . . ? C8 N3 C11 C10 0.4(5) . . . . ? C8 C9 C10 C11 -0.1(5) . . . . ? C8 C9 C10 C12 179.9(6) . . . . ? C9 C10 C11 N3 -0.2(5) . . . . ? C9 C10 C11 N4 178.3(4) . . . . ? C9 C10 C12 C13 -177.8(6) . . . . ? C10 C12 C13 C14 -1.2(8) . . . . ? C11 N3 C8 C9 -0.5(5) . . . . ? C11 N4 C14 C13 1.1(7) . . . . ? C11 C10 C12 C13 2.3(7) . . . . ? C12 C10 C11 N3 179.8(4) . . . . ? C12 C10 C11 N4 -1.8(7) . . . . ? C12 C13 C14 N4 -0.5(7) . . . . ? C14 N4 C11 N3 178.4(4) . . . . ? C14 N4 C11 C10 0.1(7) . . . . ?