# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H8 Co N4 O5' _chemical_formula_weight 299.11 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 7.604(3) _cell_length_b 7.312(3) _cell_length_c 18.317(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1018.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1873 _cell_measurement_theta_min 3.74 _cell_measurement_theta_max 27.50 _exptl_crystal_description cube _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.951 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 1.708 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4652 _exptl_absorpt_correction_T_max 0.7527 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.5 _diffrn_reflns_number 5850 _diffrn_reflns_av_R_equivalents 0.0523 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 27.53 _reflns_number_total 1252 _reflns_number_gt 775 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The water hydrogen atoms were located from the difference Fourier map and refined with restrained O-H and H...H distances using the following instructions DFIX 0.86 O3 H3wa O3 H3wb DANG 1.39 H3wa H3wb ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1011P)^2^+2.4314P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1252 _refine_ls_number_parameters 102 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0921 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1750 _refine_ls_wR_factor_gt 0.1509 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.955 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 Co1 Co 0.5000 0.0000 0.5000 0.0243(3) Uani 1 2 d S . . C1 C 0.5445(10) 0.2500 0.6362(4) 0.0318(15) Uani 1 2 d S . . C2 C 0.5246(8) 0.2500 0.7192(3) 0.0298(15) Uani 1 2 d S . . C3 C 0.5151(7) 0.0895(6) 0.7573(3) 0.0434(14) Uani 1 1 d . . . H3A H 0.5200 -0.0212 0.7324 0.052 Uiso 1 1 calc R . . C4 C 0.4984(7) 0.0902(7) 0.8325(3) 0.0402(13) Uani 1 1 d . . . H4A H 0.4925 -0.0196 0.8580 0.048 Uiso 1 1 calc R . . C5 C 0.4838(8) 0.2500 0.9487(4) 0.0282(14) Uani 1 2 d S . . H5A H 0.4228 0.3567 0.9658 0.034 Uiso 1 1 d R . . C6 C 0.6753(9) 0.2500 0.9770(3) 0.0290(14) Uani 1 2 d S . . N1 N 0.5784(8) 0.2500 0.4535(3) 0.0320(13) Uani 1 2 d S . . N2 N 0.6667(9) 0.2500 0.3985(3) 0.0392(14) Uani 1 2 d S . . N3 N 0.7429(12) 0.2500 0.3449(4) 0.070(3) Uani 1 2 d S . . N4 N 0.4908(6) 0.2500 0.8685(3) 0.0275(12) Uani 1 2 d S . . O1 O 0.5510(6) 0.0976(5) 0.60686(17) 0.0473(10) Uani 1 1 d . . . O2 O 0.7418(5) 0.0970(5) 0.9857(2) 0.0486(10) Uani 1 1 d . . . O3 O 0.7549(12) 0.2500 0.1559(5) 0.100(3) Uani 1 2 d SD . . H3WA H 0.826(12) 0.2500 0.193(4) 0.150 Uiso 1 2 d SD . . H3WB H 0.819(13) 0.2500 0.1167092(3) 0.150 Uiso 1 2 d SD . . 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 Co1 0.0345(5) 0.0170(5) 0.0214(5) -0.0009(3) 0.0030(4) -0.0001(4) C1 0.046(4) 0.025(3) 0.024(3) 0.000 0.001(3) 0.000 C2 0.039(4) 0.028(3) 0.022(3) 0.000 -0.003(3) 0.000 C3 0.081(4) 0.023(2) 0.027(2) -0.002(2) -0.003(2) 0.002(3) C4 0.069(4) 0.026(3) 0.025(2) 0.002(2) 0.000(2) -0.001(3) C5 0.033(4) 0.023(3) 0.028(3) 0.000 0.003(3) 0.000 C6 0.041(4) 0.024(3) 0.022(3) 0.000 0.002(3) 0.000 N1 0.049(3) 0.020(3) 0.027(3) 0.000 0.010(3) 0.000 N2 0.049(4) 0.027(3) 0.041(3) 0.000 0.012(3) 0.000 N3 0.103(7) 0.044(4) 0.063(5) 0.000 0.056(5) 0.000 N4 0.035(3) 0.026(3) 0.022(3) 0.000 0.001(2) 0.000 O1 0.089(3) 0.032(2) 0.0213(16) -0.0048(15) -0.0024(18) -0.007(2) O2 0.044(2) 0.030(2) 0.073(3) -0.0035(18) -0.0123(19) 0.0028(18) O3 0.110(7) 0.080(5) 0.110(6) 0.000 -0.003(5) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Co1 O2 2.104(4) 2_654 ? Co1 O2 2.104(4) 6_557 ? Co1 N1 2.103(3) . ? Co1 N1 2.103(3) 5_656 ? Co1 O1 2.119(3) . ? Co1 O1 2.119(3) 5_656 ? C1 O1 1.238(4) 7_565 ? C1 O1 1.238(4) . ? C1 C2 1.528(9) . ? C2 C3 1.367(6) . ? C2 C3 1.367(6) 7_565 ? C3 C4 1.383(7) . ? C4 N4 1.343(6) . ? C5 N4 1.470(8) . ? C5 C6 1.546(9) . ? C6 O2 1.238(5) . ? C6 O2 1.238(5) 7_565 ? N1 N2 1.211(8) . ? N1 Co1 2.103(3) 3_656 ? N2 N3 1.140(8) . ? N4 C4 1.343(6) 7_565 ? O2 Co1 2.104(4) 2_655 ? 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 O2 Co1 O2 180 2_654 6_557 ? O2 Co1 N1 88.74(19) 2_654 . ? O2 Co1 N1 91.27(19) 6_557 . ? O2 Co1 N1 91.27(19) 2_654 5_656 ? O2 Co1 N1 88.73(19) 6_557 5_656 ? N1 Co1 N1 180 . 5_656 ? O2 Co1 O1 93.30(16) 2_654 . ? O2 Co1 O1 86.70(16) 6_557 . ? N1 Co1 O1 91.70(17) . . ? N1 Co1 O1 88.30(17) 5_656 . ? O2 Co1 O1 86.70(16) 2_654 5_656 ? O2 Co1 O1 93.30(16) 6_557 5_656 ? N1 Co1 O1 88.30(17) . 5_656 ? N1 Co1 O1 91.70(17) 5_656 5_656 ? O1 Co1 O1 180 . 5_656 ? O1 C1 O1 128.3(6) 7_565 . ? O1 C1 C2 115.9(3) 7_565 . ? O1 C1 C2 115.9(3) . . ? C3 C2 C3 118.3(6) . 7_565 ? C3 C2 C1 120.8(3) . . ? C3 C2 C1 120.9(3) 7_565 . ? C2 C3 C4 120.6(5) . . ? N4 C4 C3 119.8(4) . . ? N4 C5 C6 107.5(5) . . ? O2 C6 O2 129.3(7) . 7_565 ? O2 C6 C5 115.3(3) . . ? O2 C6 C5 115.3(3) 7_565 . ? N2 N1 Co1 119.64(13) . . ? N2 N1 Co1 119.64(13) . 3_656 ? Co1 N1 Co1 120.7(3) . 3_656 ? N3 N2 N1 176.8(9) . . ? C4 N4 C4 120.9(6) . 7_565 ? C4 N4 C5 119.5(3) . . ? C4 N4 C5 119.5(3) 7_565 . ? C1 O1 Co1 134.2(4) . . ? C6 O2 Co1 134.6(4) . 2_655 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.896 _refine_diff_density_min -0.556 _refine_diff_density_rms 0.116 _database_code_depnum_ccdc_archive 'CCDC 653470' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2powder _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C8 H6 N4 Ni O4, H2 O' _chemical_formula_sum 'C8 H8 N4 Ni O5' _chemical_formula_weight 298.89 _chemical_melting_point ? _space_group_crystal_system orthorhombic _space_group_name_H-M_alt Pnma _space_group_name_Hall '-P 2ac 2n' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,1/2-z 4 -x,1/2+y,-z 5 -x,-y,-z 6 1/2+x,y,1/2-z 7 1/2-x,1/2+y,1/2+z 8 x,1/2-y,z _cell_length_a 7.6031(6) _cell_length_b 7.2312(6) _cell_length_c 18.195(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1000.35(16) _cell_formula_units_Z 4 _cell_measurement_temperature 295 _cell_special_details ? _exptl_crystal_density_diffrn 1.9843 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu ? _exptl_special_details ? _pd_spec_mounting ; packed powder pellet ; _pd_spec_mount_mode reflection _pd_spec_shape flat_sheet _pd_char_particle_morphology ? _pd_char_colour green _diffrn_ambient_temperature 295 _diffrn_source 'sealed X-ray tube' _diffrn_source_target Cu _diffrn_source_type ? _diffrn_measurement_device_type 'Rigaku Ultima IV' _diffrn_detector 'Scintillation counter (NaI)' _diffrn_detector_type ? _pd_meas_scan_method step _pd_meas_number_of_points 2751 _pd_meas_2theta_range_min 5 _pd_meas_2theta_range_max 60 _pd_meas_2theta_range_inc 0.02 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_monochromator None _computing_data_collection 'local program' _computing_cell_refinement 'Reflex module (Materials Studiao)' _computing_data_reduction 'local program' _computing_structure_solution 'DMOL (Materials Studiao)' _computing_structure_refinement 'Reflex module (Materials Studiao)' _computing_molecular_graphics ? _computing_publication_material ? _pd_proc_ls_profile_function pseudo-Voigt _pd_proc_ls_background_function ; 20-term polynomial background parameters ; _pd_proc_ls_pref_orient_corr 'March-Dollase (Dollase, 1986)' _pd_proc_ls_prof_R_factor 0.0510 _pd_proc_ls_prof_wR_factor 0.0667 _pd_proc_ls_prof_wR_expected ? _pd_proc_2theta_range_min 5 _pd_proc_2theta_range_max 60 _pd_proc_2theta_range_inc 0.02 loop_ _pd_proc_wavelength 1.54056 1.54439 _refine_ls_structure_factor_coef Inet _refine_ls_matrix_type fullcycle _refine_ls_weighting_scheme sigma _refine_ls_weighting_details "w~i~ = 1/ I~exp~(2\q~i~) '" _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_parameters 21 _refine_ls_number_restraints ? _refine_ls_number_constraints ? _refine_ls_goodness_of_fit_all ? _refine_ls_R_I_factor ? _refine_ls_restrained_S_all ? _refine_ls_shift/su_max ? _refine_ls_shift/su_mean ? loop_ _restr_rigid_body_id _restr_rigid_body_atom_site_label _restr_rigid_body_site_symmetry _restr_rigid_body_class_id _restr_rigid_body_details 1 C1 1_555 1 ? 2 C2 1_555 1 ? 3 C3 1_555 1 ? 4 C4 1_555 1 ? 5 C5 1_555 1 ? 6 C6 1_555 1 ? 7 O1 1_555 1 ? 8 O2 1_555 1 ? 9 N4 1_555 1 ? 10 H3A 1_555 1 ? 11 H4A 1_555 1 ? 12 H5A 1_555 1 ? 13 C3 8_555 1 ? 14 C4 8_555 1 ? 15 O1 8_555 1 ? 16 O2 8_555 1 ? 17 H3A 8_555 1 ? 18 H4A 8_555 1 ? 19 H5A 8_555 1 ? 20 N1 1_555 2 ? 21 N2 1_555 2 ? 22 N3 1_555 2 ? 23 O3 1_555 3 ? 24 H3wa 1_555 3 ? 25 H3wb 1_555 3 ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_adp_type _atom_site_occupancy Ni1 Ni 0.50000 0.00000 0.50000 Uiso 1.00 C1 C 0.5267(6) 0.25000 0.6403(3) Uiso 1.00 C2 C 0.5152(6) 0.25000 0.7225(3) Uiso 1.00 C3 C 0.5091(6) 0.08434 0.7616(3) Uiso 1.00 H3A H 0.5093(6) -0.04725 0.7340(3) Uiso 1.00 C4 C 0.4970(6) 0.08686 0.8380(3) Uiso 1.00 H4A H 0.4851(6) -0.03800 0.8704(3) Uiso 1.00 H5A H 0.4162(6) 0.37390 0.9742(3) Uiso 1.00 C5 C 0.4851(6) 0.25000 0.9556(3) Uiso 1.00 C6 C 0.6779(6) 0.25000 0.9827(3) Uiso 1.00 N1 N 0.5886(9) 0.25000 0.4577(5) Uiso 1.00 N2 N 0.6691(9) 0.25000 0.4013(5) Uiso 1.00 N3 N 0.7431(9) 0.25000 0.3461(5) Uiso 1.00 N4 N 0.4896(6) 0.25000 0.8749(7) Uiso 1.00 O1 O 0.5336(6) 0.09142 0.6102(3) Uiso 1.00 O2 O 0.7452(6) 0.09160 0.9907(3) Uiso 1.00 O3 O 0.7092(14) 0.25000 0.1563(7) Uiso 1.00 H3WA H 0.7598(14) 0.25000 0.2056(7) Uiso 1.00 H3WB H 0.8076(14) 0.25000 0.1216(7) Uiso 1.00 _atom_site_U_iso_or_equiv 0.00268 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ni1 N1 . . 2.077(4) no Ni1 O1 . . 2.127(5) no Ni1 O2 . 6_456 2.054(4) no C1 O1 . 8_555 1.2719(33) no C1 C2 . . 1.4982(77) no C2 C3 . 8_555 1.3940(39) no C3 C2 . . 1.3940(39) no C3 C4 . . 1.3933(77) no C3 H3A . . 1.0759(36) no C4 N4 . . 1.3585(69) no C4 H4A . . 1.0821(42) no C5 C6 . . 1.5466(66) no C5 N4 . . 1.4687(139) no C5 H5A . . 1.0916(39) no C6 O2 . 8_555 1.2629(28) no O1 C1 . . 1.2719(33) no O2 C6 . . 1.2629(28) no N1 N2 . . 1.1949(121) no N2 N3 . . 1.1512(122) no N4 C4 . 8_555 1.3585(69) no O3 H3WA . . 0.9760(176) no O3 H3WB . . 0.9790(163) no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 Ni1 O1 . . 5_656 180 no N1 Ni1 N1 . . 4_646 180 no O1 Ni1 N1 . . 4_646 87.716(3) no N1 Ni1 O2 . . 6_456 93.195(3) no O1 Ni1 N1 . . . 92.284(4) no N1 Ni1 O2 . . 2_654 86.805(3) no O1 Ni1 O2 . . 2_654 93.704(4) no O2 Ni1 O2 6_456 . 2_654 180 no O1 Ni1 O2 . . 6_456 86.296(4) no N2 N1 Ni1 . . . 118.971(4) no C1 O1 Ni1 . . . 132.945(4) no C6 O2 Ni1 . . 2_655 133.156(4) no O1 C1 O1 . . 8_555 128.738(3) no O2 C6 O2 . . 8_555 130.175(3) no O1 C1 C2 . . . 115.612(6) no O2 C6 C5 . . . 114.883(6) no C3 C2 C3 . . 8_555 118.483(3) no C3 C2 C1 . . . 120.758(6) no C4 C3 C2 . . . 120.009(6) no N3 N2 N1 . . . 178.4(10) no N4 C4 C3 . . . 120.476(6) no N4 C5 C6 . . . 107.3(4) no C4 N4 C4 . . 8_555 120.537(3) no C4 N4 C5 . . . 119.672(6) no Ni1 N1 Ni1 . . 4_656 121.000(2) no _database_code_depnum_ccdc_archive 'CCDC 943089'