# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef '1.cif' _publ_section_acknowledgements ; ? ; #Added by publCIF _audit_update_record ; ? 2011-05-27 # Formatted by IUCr publCIF system 2011-06-21 # Formatted by publCIF ; # 1. SUBMISSION DETAILS _publ_contact_author_name 'Stanislav I, Gurskiy' _publ_contact_author_address ; Chemistry Department, Moscow State University, 119991 Moscow, Russia ; _publ_contact_author_email STANISLAV.GURSKIY@GMAIL.COM _publ_contact_author_fax '+ 7-495-9390998' _publ_contact_author_phone '+ 7-495-9393654' _publ_requested_category ? _publ_contact_letter ; Please consider this CIF submission for publication in CrystEngComm. ; #==================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic 2011-05-27 _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ? _journal_techeditor_code ? _iucr_compatibility_tag ? _journal_paper_category ? _journal_techeditor_notes ? _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #=================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; ? ; # loop_ _publ_author_name _publ_author_address S.I.Gurskiy ; Chemistry Department, Moscow State University, 119991 Moscow, Russia ; V.A.Tafeenko ; Chemistry Department, Moscow State University, 119991 Moscow, Russia ; #==================================================================== # 4. TEXT _publ_section_abstract ; ? ; _publ_section_related_literature ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; _exptl_special_details ; ? ; _publ_section_references ; ? ; _publ_section_figure_captions ; ? ; data_red _database_code_depnum_ccdc_archive 'CCDC 845136' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Poly[[diaquabis(\m~2~-3-cyano-4-dicyanomethylene-5-oxo- 4,5-dihydro-1H-pyrrol-2-olato-\k^2^N^3^:N^3'^)copper(II)] dihydrate] ; _chemical_name_common ? _chemical_melting_point 488 _chemical_formula_moiety 'C16 H6 Cu N8 O6, 2(H2 O)' _chemical_formula_sum 'C16 H10 Cu N8 O8' _chemical_formula_weight 505.86 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' Cu Cu -1.9646 0.5888 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.9657(19) _cell_length_b 10.8842(11) _cell_length_c 11.7477(12) _cell_angle_alpha 90.00 _cell_angle_beta 125.406(12) _cell_angle_gamma 90.00 _cell_volume 1976.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 32 _cell_measurement_theta_max 40 _exptl_crystal_description prism _exptl_crystal_colour 'black red' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.700 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1020 _exptl_absorpt_coefficient_mu 2.172 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometr' _diffrn_measurement_method 'non-profiled omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2057 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.97 _diffrn_reflns_theta_max 72.92 _reflns_number_total 1962 _reflns_number_gt 1780 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989' _computing_cell_refinement 'CAD-4 Software (Enraf-Nonius, 1989' _computing_data_reduction 'XCAD-4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2000; ' _computing_publication_material SHELXL-97 _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. ; _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^)+(0.0631P)^2^+1.8621P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00182(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1962 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1054 _refine_ls_wR_factor_gt 0.1026 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _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 Cu1 Cu 0.2500 0.7500 0.0000 0.02693(19) Uani 1 2 d S . . O1 O 0.05963(14) 1.36056(18) -0.33947(19) 0.0525(5) Uani 1 1 d . . . O2 O 0.18774(14) 1.39450(16) 0.12737(19) 0.0528(5) Uani 1 1 d . . . N1 N 0.12401(15) 1.41051(19) -0.1088(2) 0.0393(5) Uani 1 1 d . . . N2 N 0.06556(17) 1.0196(2) -0.3212(2) 0.0540(6) Uani 1 1 d . . . N3 N 0.20417(13) 0.90500(17) 0.02996(19) 0.0346(4) Uani 1 1 d . . . N4 N 0.23713(14) 1.17796(16) 0.33463(19) 0.0349(4) Uani 1 1 d . . . C2 C 0.09554(16) 1.3305(2) -0.2184(2) 0.0370(5) Uani 1 1 d . . . C3 C 0.11542(15) 1.2058(2) -0.1594(2) 0.0326(5) Uani 1 1 d . . . C4 C 0.15368(15) 1.21364(19) -0.0183(2) 0.0292(4) Uani 1 1 d . . . C5 C 0.15825(15) 1.34994(19) 0.0147(2) 0.0344(5) Uani 1 1 d . . . C6 C 0.08982(16) 1.1016(2) -0.2466(2) 0.0370(5) Uani 1 1 d . . . C7 C 0.18701(15) 1.12452(19) 0.0867(2) 0.0294(4) Uani 1 1 d . . . C8 C 0.19560(14) 1.00122(19) 0.0582(2) 0.0291(4) Uani 1 1 d . . . C9 C 0.21531(15) 1.15460(18) 0.2241(2) 0.0303(5) Uani 1 1 d . . . O3 O 0.38889(12) 0.82916(15) 0.14329(18) 0.0369(4) Uani 1 1 d . . . O4 O 0.50224(16) 0.7363(2) 0.0875(2) 0.0499(5) Uani 1 1 d . . . H1 H 0.114(2) 1.483(4) -0.122(4) 0.063(10) Uiso 1 1 d . . . H3 H 0.413(2) 0.808(4) 0.224(4) 0.064(10) Uiso 1 1 d . . . H31 H 0.418(2) 0.795(4) 0.119(4) 0.070(11) Uiso 1 1 d . . . H4 H 0.490(3) 0.764(3) 0.030(4) 0.056(12) Uiso 1 1 d . . . H41 H 0.513(4) 0.674(5) 0.100(6) 0.11(2) 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 Cu1 0.0455(3) 0.0162(2) 0.0221(3) 0.00143(14) 0.0213(2) 0.00271(16) O1 0.0766(13) 0.0397(10) 0.0376(10) 0.0099(8) 0.0311(10) 0.0064(9) O2 0.0830(14) 0.0275(9) 0.0386(10) -0.0085(8) 0.0300(10) -0.0019(9) N1 0.0570(13) 0.0214(9) 0.0403(11) 0.0022(8) 0.0287(10) 0.0018(9) N2 0.0741(16) 0.0400(12) 0.0373(12) -0.0093(10) 0.0262(11) 0.0037(11) N3 0.0542(11) 0.0231(9) 0.0281(9) 0.0002(7) 0.0247(9) 0.0039(8) N4 0.0563(12) 0.0224(8) 0.0296(9) -0.0027(7) 0.0270(9) -0.0012(8) C2 0.0464(13) 0.0312(12) 0.0351(12) 0.0037(9) 0.0246(10) 0.0024(10) C3 0.0461(12) 0.0237(10) 0.0306(11) -0.0007(8) 0.0238(10) 0.0006(9) C4 0.0406(11) 0.0203(9) 0.0308(10) -0.0018(8) 0.0231(9) 0.0000(8) C5 0.0463(12) 0.0207(10) 0.0360(12) -0.0019(8) 0.0238(10) -0.0011(9) C6 0.0511(13) 0.0314(12) 0.0281(10) 0.0013(9) 0.0228(10) 0.0053(10) C7 0.0460(12) 0.0201(9) 0.0266(10) -0.0034(8) 0.0236(9) -0.0005(8) C8 0.0424(11) 0.0233(10) 0.0236(9) 0.0007(8) 0.0204(9) 0.0008(8) C9 0.0439(12) 0.0195(9) 0.0313(11) -0.0018(8) 0.0239(10) 0.0000(8) O3 0.0472(10) 0.0299(8) 0.0302(8) 0.0028(7) 0.0205(8) 0.0040(7) O4 0.0665(14) 0.0432(12) 0.0360(11) -0.0013(9) 0.0274(10) 0.0024(10) _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 Cu1 N4 1.9746(17) 4_545 ? Cu1 N4 1.9746(17) 6_575 ? Cu1 N3 2.0199(18) . ? Cu1 N3 2.0199(18) 7_565 ? Cu1 O3 2.3188(18) 7_565 ? Cu1 O3 2.3188(18) . ? O1 C2 1.213(3) . ? O2 C5 1.201(3) . ? N1 C5 1.366(3) . ? N1 C2 1.379(3) . ? N1 H1 0.80(4) . ? N2 C6 1.144(3) . ? N3 C8 1.138(3) . ? N4 C9 1.140(3) . ? N4 Cu1 1.9746(17) 4 ? C2 C3 1.470(3) . ? C3 C4 1.374(3) . ? C3 C6 1.413(3) . ? C4 C7 1.399(3) . ? C4 C5 1.523(3) . ? C7 C9 1.414(3) . ? C7 C8 1.415(3) . ? O3 H3 0.81(4) . ? O3 H31 0.84(4) . ? O4 H4 0.65(4) . ? O4 H41 0.71(5) . ? 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 N4 Cu1 N4 180.00(9) 4_545 6_575 ? N4 Cu1 N3 88.89(7) 4_545 . ? N4 Cu1 N3 91.11(7) 6_575 . ? N4 Cu1 N3 91.11(7) 4_545 7_565 ? N4 Cu1 N3 88.89(7) 6_575 7_565 ? N3 Cu1 N3 180.0 . 7_565 ? N4 Cu1 O3 90.43(8) 4_545 7_565 ? N4 Cu1 O3 89.57(8) 6_575 7_565 ? N3 Cu1 O3 90.82(7) . 7_565 ? N3 Cu1 O3 89.18(7) 7_565 7_565 ? N4 Cu1 O3 89.57(8) 4_545 . ? N4 Cu1 O3 90.43(8) 6_575 . ? N3 Cu1 O3 89.18(7) . . ? N3 Cu1 O3 90.82(7) 7_565 . ? O3 Cu1 O3 180.0 7_565 . ? C5 N1 C2 111.99(19) . . ? C5 N1 H1 126(3) . . ? C2 N1 H1 121(3) . . ? C8 N3 Cu1 165.4(2) . . ? C9 N4 Cu1 164.94(19) . 4 ? O1 C2 N1 125.1(2) . . ? O1 C2 C3 128.1(2) . . ? N1 C2 C3 106.73(19) . . ? C4 C3 C6 130.1(2) . . ? C4 C3 C2 108.9(2) . . ? C6 C3 C2 120.9(2) . . ? C3 C4 C7 132.3(2) . . ? C3 C4 C5 106.24(19) . . ? C7 C4 C5 121.40(19) . . ? O2 C5 N1 127.3(2) . . ? O2 C5 C4 126.5(2) . . ? N1 C5 C4 106.15(19) . . ? N2 C6 C3 176.9(3) . . ? C4 C7 C9 121.65(19) . . ? C4 C7 C8 120.27(18) . . ? C9 C7 C8 118.05(19) . . ? N3 C8 C7 175.5(2) . . ? N4 C9 C7 179.0(3) . . ? Cu1 O3 H3 112(3) . . ? Cu1 O3 H31 106(3) . . ? H3 O3 H31 103(4) . . ? H4 O4 H41 124(5) . . ? 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 O3 H31 O4 0.84(4) 1.95(4) 2.776(3) 169(4) . O3 H3 O4 0.81(4) 1.99(4) 2.779(3) 163(4) 2_655 O4 H4 O1 0.65(4) 2.13(4) 2.781(3) 175(5) 4_544 O4 H41 N2 0.71(5) 2.28(5) 2.976(4) 170(6) 8_566 N1 H1 O3 0.80(4) 2.06(4) 2.853(3) 170(3) 7_575 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 72.92 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.396 _refine_diff_density_min -0.552 _refine_diff_density_rms 0.111 data_bronze _database_code_depnum_ccdc_archive 'CCDC 845137' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tetraaquabis(3-cyano-4-dicyanomethylene-5-oxo-4,5-dihydro-1H-pyrrol-2- olato)copper(II) ; _chemical_name_common ? _chemical_melting_point 460 _chemical_formula_moiety 'C16 H6 Cu N8 O6, 2(H2 O)' _chemical_formula_sum 'C16 H10 Cu N8 O8' _chemical_formula_weight 505.86 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' _symmetry_cell_setting TRICLINIC _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9985(9) _cell_length_b 8.0047(11) _cell_length_c 9.5314(14) _cell_angle_alpha 88.986(11) _cell_angle_beta 68.710(13) _cell_angle_gamma 84.342(13) _cell_volume 495.00(12) _cell_formula_units_Z 1 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 14 _cell_measurement_theta_max 18 _exptl_crystal_description PRISM _exptl_crystal_colour BROWN _exptl_crystal_size_max .2 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.697 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 255 _exptl_absorpt_coefficient_mu 1.169 _exptl_absorpt_correction_type NONE _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 'Enraf-Nonius CAD-4 diffractometr' _diffrn_measurement_method 'non-profiled omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% ? _diffrn_reflns_number 2523 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.96 _reflns_number_total 2383 _reflns_number_gt 1764 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989' _computing_cell_refinement 'CAD-4 Software (Enraf-Nonius, 1989' _computing_data_reduction 'XCAD-4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2000; ' _computing_publication_material SHELXL-97 _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. ; _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^)+(0.0564P)^2^+0.0476P] 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 2383 _refine_ls_number_parameters 171 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1157 _refine_ls_wR_factor_gt 0.1044 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 Cu1 Cu 0.5000 0.0000 0.0000 0.0308(2) Uani 1 2 d S . . O1 O -0.2055(4) 0.9088(3) 0.3127(3) 0.0431(6) Uani 1 1 d . . . O2 O 0.2142(4) 0.4657(3) 0.0437(3) 0.0464(7) Uani 1 1 d . . . O3 O 0.7059(4) 0.1353(4) 0.1144(3) 0.0380(6) Uani 1 1 d . . . O4 O 0.5091(5) -0.2013(3) 0.1152(3) 0.0469(8) Uani 1 1 d . . . N1 N 0.0250(5) 0.7116(3) 0.1468(3) 0.0366(7) Uani 1 1 d . . . N2 N -0.4473(5) 0.6356(4) 0.6415(3) 0.0463(8) Uani 1 1 d . . . N3 N -0.2552(5) 0.2127(4) 0.5918(3) 0.0467(8) Uani 1 1 d . . . N4 N 0.2421(4) 0.0981(3) 0.1577(3) 0.0336(7) Uani 1 1 d . . . C2 C -0.1308(5) 0.7647(4) 0.2830(4) 0.0309(7) Uani 1 1 d . . . C3 C -0.1791(5) 0.6164(4) 0.3743(3) 0.0291(7) Uani 1 1 d . . . C4 C -0.0537(5) 0.4788(4) 0.2963(3) 0.0267(7) Uani 1 1 d . . . C5 C 0.0827(5) 0.5447(4) 0.1453(4) 0.0310(7) Uani 1 1 d . . . C6 C -0.3290(5) 0.6252(4) 0.5219(4) 0.0312(7) Uani 1 1 d . . . C7 C -0.0342(5) 0.3096(4) 0.3322(3) 0.0268(7) Uani 1 1 d . . . C8 C -0.1574(5) 0.2524(4) 0.4753(3) 0.0297(7) Uani 1 1 d . . . C9 C 0.1180(5) 0.1934(4) 0.2345(3) 0.0288(7) Uani 1 1 d . . . H1 H 0.088(7) 0.769(5) 0.072(5) 0.056(13) Uiso 1 1 d . . . H3 H 0.731(7) 0.074(5) 0.167(5) 0.047(14) Uiso 1 1 d . . . H31 H 0.640(7) 0.202(5) 0.157(5) 0.043(13) Uiso 1 1 d . . . H4 H 0.433(7) -0.197(5) 0.203(5) 0.057(13) Uiso 1 1 d . . . H41 H 0.564(7) -0.264(6) 0.086(5) 0.048(15) 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 Cu1 0.0326(3) 0.0244(3) 0.0228(3) 0.0014(2) 0.0035(2) 0.0032(2) O1 0.0499(15) 0.0265(12) 0.0456(15) -0.0014(10) -0.0104(12) 0.0031(10) O2 0.0486(15) 0.0342(13) 0.0334(13) 0.0015(10) 0.0100(11) 0.0046(11) O3 0.0459(16) 0.0297(13) 0.0302(13) -0.0016(11) -0.0060(12) 0.0040(12) O4 0.0585(19) 0.0283(14) 0.0298(14) 0.0053(11) 0.0084(13) 0.0121(13) N1 0.0417(17) 0.0271(14) 0.0306(15) 0.0049(12) -0.0008(13) -0.0035(12) N2 0.0419(18) 0.0496(19) 0.0339(16) -0.0132(14) 0.0021(14) -0.0009(14) N3 0.0510(19) 0.0473(18) 0.0274(15) 0.0049(13) 0.0020(14) -0.0017(15) N4 0.0341(15) 0.0256(13) 0.0279(13) 0.0002(11) 0.0036(12) 0.0012(11) C2 0.0318(17) 0.0266(15) 0.0321(17) -0.0011(13) -0.0092(14) -0.0013(13) C3 0.0292(16) 0.0277(15) 0.0250(15) -0.0033(12) -0.0035(13) -0.0018(12) C4 0.0248(15) 0.0287(15) 0.0229(14) -0.0012(12) -0.0038(12) -0.0043(12) C5 0.0315(17) 0.0278(15) 0.0278(16) 0.0010(12) -0.0034(13) -0.0043(13) C6 0.0284(17) 0.0267(15) 0.0358(18) -0.0057(13) -0.0089(14) 0.0007(13) C7 0.0261(15) 0.0271(15) 0.0220(14) -0.0012(11) -0.0028(12) -0.0017(12) C8 0.0292(16) 0.0265(15) 0.0275(16) -0.0021(12) -0.0047(13) 0.0039(12) C9 0.0314(17) 0.0251(15) 0.0236(15) 0.0054(12) -0.0020(13) -0.0052(13) _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 Cu1 O4 1.943(3) 2_655 ? Cu1 O4 1.943(3) . ? Cu1 N4 1.982(2) . ? Cu1 N4 1.982(2) 2_655 ? Cu1 O3 2.435(3) . ? Cu1 O3 2.435(3) 2_655 ? O1 C2 1.212(4) . ? O2 C5 1.202(4) . ? O3 H3 0.75(4) . ? O3 H31 0.69(4) . ? O4 H4 0.81(5) . ? O4 H41 0.61(4) . ? N1 C5 1.356(4) . ? N1 C2 1.398(4) . ? N1 H1 0.85(4) . ? N2 C6 1.139(4) . ? N3 C8 1.132(4) . ? N4 C9 1.139(4) . ? C2 C3 1.452(4) . ? C3 C4 1.379(4) . ? C3 C6 1.415(4) . ? C4 C7 1.396(4) . ? C4 C5 1.528(4) . ? C7 C9 1.408(4) . ? C7 C8 1.420(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 O4 Cu1 O4 180.00(16) 2_655 . ? O4 Cu1 N4 87.75(12) 2_655 . ? O4 Cu1 N4 92.25(12) . . ? O4 Cu1 N4 92.25(12) 2_655 2_655 ? O4 Cu1 N4 87.75(12) . 2_655 ? N4 Cu1 N4 180.0(2) . 2_655 ? O4 Cu1 O3 88.93(13) 2_655 . ? O4 Cu1 O3 91.07(13) . . ? N4 Cu1 O3 90.91(11) . . ? N4 Cu1 O3 89.09(11) 2_655 . ? O4 Cu1 O3 91.07(13) 2_655 2_655 ? O4 Cu1 O3 88.93(13) . 2_655 ? N4 Cu1 O3 89.09(11) . 2_655 ? N4 Cu1 O3 90.91(11) 2_655 2_655 ? O3 Cu1 O3 180.00(10) . 2_655 ? Cu1 O3 H3 108(3) . . ? Cu1 O3 H31 105(4) . . ? H3 O3 H31 108(5) . . ? Cu1 O4 H4 116(3) . . ? Cu1 O4 H41 121(5) . . ? H4 O4 H41 122(6) . . ? C5 N1 C2 111.7(3) . . ? C5 N1 H1 119(3) . . ? C2 N1 H1 129(3) . . ? C9 N4 Cu1 161.4(3) . . ? O1 C2 N1 124.2(3) . . ? O1 C2 C3 129.2(3) . . ? N1 C2 C3 106.7(3) . . ? C4 C3 C6 128.7(3) . . ? C4 C3 C2 109.4(3) . . ? C6 C3 C2 121.8(3) . . ? C3 C4 C7 132.8(3) . . ? C3 C4 C5 105.8(3) . . ? C7 C4 C5 121.4(3) . . ? O2 C5 N1 126.1(3) . . ? O2 C5 C4 127.5(3) . . ? N1 C5 C4 106.4(3) . . ? N2 C6 C3 178.2(4) . . ? C4 C7 C9 121.8(3) . . ? C4 C7 C8 120.4(3) . . ? C9 C7 C8 117.6(3) . . ? N3 C8 C7 177.2(4) . . ? N4 C9 C7 178.7(4) . . ? 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 N1 H1 O3 0.85(4) 2.03(4) 2.862(4) 166(4) 2_665 O4 H4 N3 0.81(5) 1.91(5) 2.717(4) 174(4) 2_556 O4 H41 O2 0.61(4) 2.17(5) 2.775(4) 171(6) 2_655 O3 H3 O1 0.75(4) 2.03(5) 2.785(4) 179(5) 1_645 O3 H31 N2 0.69(4) 2.25(4) 2.914(4) 160(5) 2_566 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.96 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.506 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.084 data_cu15 _database_code_depnum_ccdc_archive 'CCDC 845138' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tetraaquabis(3-cyano-4-dicyanomethylene-5-oxo-4,5-dihydro-1H-pyrrol-2- olato)copper(II) half-hydrate ; _chemical_name_common ? _chemical_melting_point 430 _chemical_formula_moiety 'C16 H10 Cu N8 O8, O' _chemical_formula_sum 'C16 H10 Cu N8 O9' _chemical_formula_weight 521.86 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' Cu Cu -1.9646 0.5888 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.400(2) _cell_length_b 8.849(3) _cell_length_c 11.531(5) _cell_angle_alpha 88.24(2) _cell_angle_beta 77.28(2) _cell_angle_gamma 82.33(3) _cell_volume 532.7(4) _cell_formula_units_Z 1 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 33 _cell_measurement_theta_max 45 _exptl_crystal_description prism _exptl_crystal_colour 'DARK GREEN' _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 263 _exptl_absorpt_coefficient_mu 2.072 _exptl_absorpt_correction_type refdelf _exptl_absorpt_factor_muR 0.084 _exptl_absorpt_process_details ; Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166 ; _exptl_absorpt_correction_T_min 0.4499 _exptl_absorpt_correction_T_max 0.9191 _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometr' _diffrn_measurement_method 'non-profiled omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% ? _diffrn_reflns_number 2049 _diffrn_reflns_av_R_equivalents 0.03 _diffrn_reflns_av_sigmaI/netI 0.0141 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.93 _diffrn_reflns_theta_max 72.90 _reflns_number_total 2049 _reflns_number_gt 1867 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989' _computing_cell_refinement 'CAD-4 Software (Enraf-Nonius, 1989' _computing_data_reduction 'XCAD-4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2000; ' _computing_publication_material SHELXL-97 _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. ; _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^)+(0.0812P)^2^+0.3087P] 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 2049 _refine_ls_number_parameters 183 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1430 _refine_ls_wR_factor_gt 0.1401 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.092 _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 Cu1 Cu 0.0000 0.0000 0.0000 0.0577(3) Uani 1 2 d SD . . O1 O 0.5319(5) 0.3984(3) 0.1598(2) 0.0749(7) Uani 1 1 d . . . O2 O 0.2292(4) 0.3966(2) 0.56019(19) 0.0584(5) Uani 1 1 d . . . O3 O 0.3280(6) -0.2031(3) 0.0472(2) 0.0842(8) Uani 1 1 d D . . O4 O 0.2700(6) 0.0779(4) -0.1202(2) 0.0838(8) Uani 1 1 d D . . N1 N 0.4229(5) 0.4207(3) 0.3633(2) 0.0521(6) Uani 1 1 d . . . N2 N 0.0771(5) 0.1281(3) 0.1180(2) 0.0628(7) Uani 1 1 d . . . N3 N -0.3378(5) 0.0385(3) 0.3624(2) 0.0606(6) Uani 1 1 d . . . N4 N -0.2398(7) 0.2149(4) 0.6977(3) 0.0759(8) Uani 1 1 d . . . C2 C 0.3979(5) 0.3680(3) 0.2546(3) 0.0533(6) Uani 1 1 d . . . C3 C 0.1917(5) 0.2739(3) 0.2807(2) 0.0465(6) Uani 1 1 d . . . C4 C 0.0955(5) 0.2703(3) 0.4029(2) 0.0430(5) Uani 1 1 d . . . C5 C 0.2512(5) 0.3688(3) 0.4562(3) 0.0485(6) Uani 1 1 d . . . C6 C 0.1267(5) 0.1955(3) 0.1927(2) 0.0488(6) Uani 1 1 d . . . C7 C -0.0961(5) 0.1978(3) 0.4717(2) 0.0461(6) Uani 1 1 d . . . C8 C -0.2351(5) 0.1084(3) 0.4144(2) 0.0484(6) Uani 1 1 d . . . C9 C -0.1694(6) 0.2088(3) 0.5980(3) 0.0536(6) Uani 1 1 d . . . O10 O 0.815(6) 0.612(3) 0.086(3) 0.126(6) Uiso 0.165(10) 1 d P . . O10A O 0.916(5) 0.608(3) 0.156(3) 0.126(6) Uiso 0.170(11) 1 d P . . O10B O 0.953(6) 0.547(4) 0.092(3) 0.126(6) Uiso 0.165(12) 1 d P . . H1 H 0.516(7) 0.473(4) 0.371(3) 0.065(11) Uiso 1 1 d . . . H3 H 0.260(7) -0.271(4) 0.099(4) 0.127(10) Uiso 1 1 d D . . H31 H 0.382(9) -0.278(4) -0.005(4) 0.127(10) Uiso 1 1 d D . . H4 H 0.304(11) 0.046(7) -0.190(3) 0.127(10) Uiso 1 1 d D . . H41 H 0.377(9) 0.132(6) -0.104(5) 0.127(10) 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 Cu1 0.0599(4) 0.0699(4) 0.0430(4) -0.0055(3) 0.0024(2) -0.0285(3) O1 0.0754(15) 0.0860(16) 0.0607(14) -0.0085(12) 0.0073(11) -0.0366(12) O2 0.0616(12) 0.0607(12) 0.0531(12) -0.0081(9) -0.0115(9) -0.0087(9) O3 0.111(2) 0.0812(17) 0.0551(14) -0.0029(12) -0.0002(13) -0.0230(15) O4 0.0910(18) 0.115(2) 0.0489(13) -0.0111(13) 0.0065(12) -0.0609(16) N1 0.0482(12) 0.0488(12) 0.0585(15) -0.0059(10) -0.0062(10) -0.0109(10) N2 0.0605(15) 0.0727(16) 0.0519(15) 0.0008(13) 0.0045(11) -0.0256(12) N3 0.0557(14) 0.0598(14) 0.0655(16) 0.0016(12) -0.0067(12) -0.0164(11) N4 0.088(2) 0.082(2) 0.0528(17) 0.0004(14) -0.0021(14) -0.0125(16) C2 0.0516(14) 0.0503(14) 0.0555(16) -0.0068(12) -0.0040(12) -0.0089(11) C3 0.0445(13) 0.0452(13) 0.0477(14) -0.0041(11) -0.0035(10) -0.0078(10) C4 0.0403(12) 0.0363(11) 0.0499(14) -0.0023(10) -0.0087(10) 0.0026(9) C5 0.0447(13) 0.0405(12) 0.0564(16) -0.0025(11) -0.0078(11) 0.0039(10) C6 0.0493(14) 0.0487(13) 0.0453(14) -0.0007(12) 0.0006(11) -0.0130(11) C7 0.0469(13) 0.0399(12) 0.0474(14) 0.0019(10) -0.0060(10) 0.0006(10) C8 0.0448(13) 0.0428(13) 0.0522(15) 0.0067(11) -0.0012(11) -0.0032(10) C9 0.0568(15) 0.0483(14) 0.0524(16) 0.0021(12) -0.0069(12) -0.0034(11) _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 Cu1 N2 1.944(3) 2 ? Cu1 N2 1.944(3) . ? Cu1 O4 1.960(2) . ? Cu1 O4 1.960(2) 2 ? O1 C2 1.215(4) . ? O2 C5 1.209(4) . ? O3 H3 0.89(3) . ? O3 H31 0.88(3) . ? O4 H4 0.84(3) . ? O4 H41 0.85(3) . ? N1 C5 1.365(4) . ? N1 C2 1.390(4) . ? N1 H1 0.75(4) . ? N2 C6 1.161(4) . ? N3 C8 1.145(4) . ? N4 C9 1.130(4) . ? C2 C3 1.452(4) . ? C3 C6 1.378(4) . ? C3 C4 1.391(4) . ? C4 C7 1.377(4) . ? C4 C5 1.517(4) . ? C7 C9 1.425(4) . ? C7 C8 1.426(4) . ? O10 O10B 0.89(3) . ? O10 O10A 1.07(4) . ? O10A O10B 0.89(3) . ? 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 N2 Cu1 N2 180.00(17) 2 . ? N2 Cu1 O4 90.77(11) 2 . ? N2 Cu1 O4 89.23(11) . . ? N2 Cu1 O4 89.23(11) 2 2 ? N2 Cu1 O4 90.77(11) . 2 ? O4 Cu1 O4 180.0(2) . 2 ? H3 O3 H31 88(4) . . ? Cu1 O4 H4 121(4) . . ? Cu1 O4 H41 123(4) . . ? H4 O4 H41 115(6) . . ? C5 N1 C2 112.0(3) . . ? C5 N1 H1 123(3) . . ? C2 N1 H1 125(3) . . ? C6 N2 Cu1 175.3(3) . . ? O1 C2 N1 123.6(3) . . ? O1 C2 C3 129.9(3) . . ? N1 C2 C3 106.5(2) . . ? C6 C3 C4 128.6(2) . . ? C6 C3 C2 121.7(2) . . ? C4 C3 C2 109.5(2) . . ? C7 C4 C3 132.1(3) . . ? C7 C4 C5 122.4(2) . . ? C3 C4 C5 105.5(2) . . ? O2 C5 N1 126.3(3) . . ? O2 C5 C4 127.2(3) . . ? N1 C5 C4 106.5(2) . . ? N2 C6 C3 178.6(3) . . ? C4 C7 C9 123.9(3) . . ? C4 C7 C8 118.9(2) . . ? C9 C7 C8 117.2(2) . . ? N3 C8 C7 176.1(3) . . ? N4 C9 C7 176.2(4) . . ? O10B O10 O10A 53(3) . . ? O10B O10A O10 53(3) . . ? O10 O10B O10A 73(3) . . ? 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 N1 H1 O2 0.75(4) 2.19(4) 2.924(4) 165(4) 2_666 O4 H41 O3 0.85(3) 2.03(3) 2.855(4) 164(6) 2_655 O4 H4 N3 0.84(3) 2.10(3) 2.935(4) 172(6) 2 O3 H31 O1 0.88(3) 2.04(3) 2.893(4) 162(3) 2_655 _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 72.90 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.483 _refine_diff_density_min -0.630 _refine_diff_density_rms 0.063 data_cu_yel _database_code_depnum_ccdc_archive 'CCDC 845139' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tetraaquabis(3-cyano-4-dicyanomethylene-5-oxo-4,5-dihydro-1H-pyrrol-2- olato)copper(II) hydrate ; _chemical_name_common ? _chemical_melting_point 440 _chemical_formula_moiety 'C16 H10 Cu N8 O8, H2 O' _chemical_formula_sum 'C16 H12 Cu N8 O9' _chemical_formula_weight 523.88 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' Cu Cu -1.9646 0.5888 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.753(1) _cell_length_b 11.707(2) _cell_length_c 14.382(2) _cell_angle_alpha 103.56(1) _cell_angle_beta 97.73(1) _cell_angle_gamma 101.01(1) _cell_volume 1065.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 29 _cell_measurement_theta_max 38 _exptl_crystal_description PRISM _exptl_crystal_colour 'LIGHT GREEN' _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 530 _exptl_absorpt_coefficient_mu 2.071 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_absorpt_correction_T_min 0.0390 _exptl_absorpt_correction_T_max 0.4430 _diffrn_ambient_temperature 290(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometr' _diffrn_measurement_method 'non-profiled omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4166 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0520 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 69.97 _reflns_number_total 4006 _reflns_number_gt 2781 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989' _computing_cell_refinement 'CAD-4 Software (Enraf-Nonius, 1989' _computing_data_reduction 'XCAD-4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2000; ' _computing_publication_material SHELXL-97 _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. ; _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^)+(0.0688P)^2^+0.8437P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4006 _refine_ls_number_parameters 354 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0922 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1533 _refine_ls_wR_factor_gt 0.1331 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _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 Cu1 Cu 0.22527(12) 0.14401(6) 0.16651(4) 0.0468(2) Uani 1 1 d . . . O3 O 0.1713(7) 0.2921(3) 0.2391(3) 0.0635(11) Uani 1 1 d D . . O4 O 0.2621(7) -0.0085(3) 0.0894(3) 0.0623(11) Uani 1 1 d . . . O5 O 0.6029(7) 0.2193(4) 0.2217(3) 0.0636(11) Uani 1 1 d . . . O6 O -0.1552(6) 0.0606(4) 0.1112(3) 0.0529(9) Uani 1 1 d . . . O1 O 0.2194(5) 0.1223(3) -0.2156(2) 0.0486(8) Uani 1 1 d . . . O2 O 0.2394(6) 0.5104(3) -0.2286(2) 0.0556(9) Uani 1 1 d . . . N1 N 0.2295(6) 0.3078(3) -0.2471(3) 0.0437(9) Uani 1 1 d . . . N2 N 0.2344(6) 0.2069(3) 0.0522(3) 0.0456(9) Uani 1 1 d . . . N3 N 0.2618(7) 0.5003(4) 0.1556(3) 0.0556(11) Uani 1 1 d . . . N4 N 0.2434(8) 0.7332(4) -0.0386(3) 0.0616(12) Uani 1 1 d . . . C2 C 0.2293(7) 0.2312(4) -0.1869(3) 0.0390(9) Uani 1 1 d . . . C3 C 0.2383(7) 0.3016(4) -0.0901(3) 0.0367(9) Uani 1 1 d . . . C4 C 0.2422(6) 0.4215(4) -0.0911(3) 0.0356(9) Uani 1 1 d . . . C5 C 0.2372(7) 0.4248(4) -0.1960(3) 0.0394(10) Uani 1 1 d . . . C6 C 0.2355(7) 0.2504(4) -0.0116(3) 0.0378(9) Uani 1 1 d . . . C7 C 0.2481(6) 0.5219(4) -0.0180(3) 0.0367(9) Uani 1 1 d . . . C8 C 0.2553(7) 0.5125(3) 0.0794(3) 0.0384(9) Uani 1 1 d . . . C9 C 0.2457(7) 0.6386(4) -0.0327(3) 0.0435(10) Uani 1 1 d . . . O1A O 0.2132(5) 0.1824(3) 0.5507(2) 0.0481(8) Uani 1 1 d . . . O2A O 0.2860(6) -0.1849(3) 0.5868(2) 0.0557(9) Uani 1 1 d . . . N1A N 0.2525(6) 0.0084(3) 0.5936(3) 0.0423(9) Uani 1 1 d . . . N2A N 0.2228(6) 0.0829(3) 0.2834(2) 0.0459(9) Uani 1 1 d . . . N3A N 0.2778(8) -0.1953(4) 0.2008(3) 0.0619(12) Uani 1 1 d . . . N4A N 0.3188(13) -0.4090(5) 0.4121(4) 0.116(3) Uani 1 1 d . . . C2A C 0.2347(6) 0.0789(4) 0.5279(3) 0.0380(9) Uani 1 1 d . . . C3A C 0.2467(6) 0.0057(4) 0.4350(3) 0.0358(9) Uani 1 1 d . . . C4A C 0.2645(6) -0.1094(4) 0.4429(3) 0.0366(9) Uani 1 1 d . . . C5A C 0.2688(7) -0.1054(4) 0.5486(3) 0.0418(10) Uani 1 1 d . . . C6A C 0.2338(6) 0.0476(3) 0.3511(3) 0.0353(9) Uani 1 1 d . . . C7A C 0.2793(7) -0.2100(4) 0.3755(3) 0.0424(10) Uani 1 1 d . . . C8A C 0.2788(7) -0.2062(4) 0.2777(3) 0.0443(10) Uani 1 1 d . . . C9A C 0.2991(10) -0.3204(4) 0.3983(4) 0.0641(15) Uani 1 1 d . . . O7 O 0.2079(15) 0.3471(4) 0.4248(4) 0.150(3) Uani 1 1 d D . . H1 H 0.222(8) 0.287(4) -0.302(4) 0.055(15) Uiso 1 1 d . . . H11 H 0.244(7) 0.035(4) 0.651(3) 0.040(12) Uiso 1 1 d . . . H3 H 0.179(9) 0.347(5) 0.226(4) 0.063(19) Uiso 1 1 d . . . H31 H 0.190(12) 0.301(7) 0.3005(17) 0.12(3) Uiso 1 1 d D . . H4 H 0.275(8) -0.059(5) 0.105(4) 0.046(16) Uiso 1 1 d . . . H41 H 0.235(13) -0.022(8) 0.035(6) 0.14(4) Uiso 1 1 d . . . H5 H 0.631(12) 0.213(6) 0.271(5) 0.10(3) Uiso 1 1 d . . . H51 H 0.616(14) 0.288(8) 0.219(6) 0.15(4) Uiso 1 1 d . . . H6 H -0.190(10) 0.014(6) 0.133(4) 0.08(2) Uiso 1 1 d . . . H61 H -0.206(10) 0.121(6) 0.136(5) 0.09(2) Uiso 1 1 d . . . H7 H 0.211(16) 0.313(8) 0.472(5) 0.17(3) Uiso 1 1 d D . . H71 H 0.276(13) 0.420(4) 0.453(6) 0.17(3) 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 Cu1 0.0547(5) 0.0455(4) 0.0433(3) 0.0147(3) 0.0102(3) 0.0145(3) O3 0.089(3) 0.052(2) 0.057(2) 0.0187(17) 0.020(2) 0.025(2) O4 0.092(3) 0.048(2) 0.0513(19) 0.0134(16) 0.011(2) 0.026(2) O5 0.058(3) 0.071(3) 0.057(2) 0.0246(18) -0.0020(18) 0.003(2) O6 0.055(3) 0.0481(19) 0.0572(19) 0.0142(16) 0.0125(17) 0.0143(18) O1 0.052(2) 0.0433(16) 0.0475(15) 0.0080(12) 0.0120(15) 0.0065(15) O2 0.063(3) 0.0569(19) 0.0531(17) 0.0229(15) 0.0107(16) 0.0175(18) N1 0.042(3) 0.048(2) 0.0386(18) 0.0136(15) 0.0061(17) 0.0025(17) N2 0.044(3) 0.0437(19) 0.0486(19) 0.0111(15) 0.0088(17) 0.0105(18) N3 0.060(3) 0.054(2) 0.052(2) 0.0126(17) 0.008(2) 0.013(2) N4 0.070(3) 0.053(2) 0.066(2) 0.0172(19) 0.018(2) 0.020(2) C2 0.026(2) 0.044(2) 0.044(2) 0.0112(17) 0.0074(17) 0.0021(18) C3 0.028(3) 0.044(2) 0.0368(18) 0.0091(16) 0.0050(17) 0.0066(18) C4 0.017(2) 0.044(2) 0.0428(19) 0.0117(16) 0.0005(16) 0.0035(17) C5 0.026(3) 0.049(2) 0.043(2) 0.0141(17) 0.0037(18) 0.0078(19) C6 0.028(3) 0.038(2) 0.045(2) 0.0074(16) 0.0046(17) 0.0070(18) C7 0.019(2) 0.042(2) 0.048(2) 0.0146(17) 0.0006(17) 0.0045(17) C8 0.027(2) 0.0355(19) 0.049(2) 0.0071(16) 0.0039(18) 0.0057(17) C9 0.032(3) 0.048(2) 0.052(2) 0.0135(18) 0.0097(19) 0.010(2) O1A 0.046(2) 0.0517(17) 0.0482(15) 0.0109(13) 0.0113(14) 0.0153(15) O2A 0.057(2) 0.0582(19) 0.0539(17) 0.0246(15) 0.0045(16) 0.0096(17) N1A 0.035(2) 0.055(2) 0.0375(17) 0.0127(15) 0.0094(16) 0.0083(17) N2A 0.044(3) 0.049(2) 0.0448(18) 0.0135(16) 0.0063(17) 0.0100(18) N3A 0.068(3) 0.062(3) 0.057(2) 0.0130(19) 0.012(2) 0.020(2) N4A 0.200(8) 0.051(3) 0.096(4) 0.019(3) 0.013(4) 0.035(4) C2A 0.019(2) 0.052(2) 0.043(2) 0.0143(17) 0.0047(17) 0.0057(18) C3A 0.021(2) 0.045(2) 0.0418(19) 0.0140(16) 0.0051(16) 0.0065(18) C4A 0.021(2) 0.045(2) 0.0429(19) 0.0124(16) 0.0037(16) 0.0053(18) C5A 0.023(3) 0.054(2) 0.047(2) 0.0171(19) 0.0022(18) 0.004(2) C6A 0.022(2) 0.039(2) 0.043(2) 0.0082(16) 0.0068(17) 0.0064(17) C7A 0.033(3) 0.043(2) 0.047(2) 0.0102(17) -0.0001(19) 0.0056(19) C8A 0.036(3) 0.043(2) 0.050(2) 0.0063(18) 0.004(2) 0.011(2) C9A 0.075(4) 0.045(3) 0.065(3) 0.008(2) 0.004(3) 0.011(3) O7 0.310(10) 0.061(3) 0.066(3) 0.015(2) 0.021(4) 0.022(4) _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 Cu1 O3 1.930(4) . ? Cu1 O4 1.949(4) . ? Cu1 N2 1.956(4) . ? Cu1 N2A 1.976(3) . ? O3 H3 0.71(5) . ? O3 H31 0.85(2) . ? O4 H4 0.69(5) . ? O4 H41 0.75(8) . ? O5 H5 0.73(7) . ? O5 H51 0.80(9) . ? O6 H6 0.71(6) . ? O6 H61 0.86(7) . ? O1 C2 1.230(5) . ? O2 C5 1.200(5) . ? N1 C5 1.383(5) . ? N1 C2 1.385(5) . ? N1 H1 0.77(5) . ? N2 C6 1.149(5) . ? N3 C8 1.133(5) . ? N4 C9 1.134(6) . ? C2 C3 1.430(5) . ? C3 C6 1.397(5) . ? C3 C4 1.403(5) . ? C4 C7 1.371(6) . ? C4 C5 1.516(5) . ? C7 C8 1.426(5) . ? C7 C9 1.433(5) . ? O1A C2A 1.221(5) . ? O2A C5A 1.203(5) . ? N1A C5A 1.370(6) . ? N1A C2A 1.401(5) . ? N1A H11 0.82(4) . ? N2A C6A 1.143(5) . ? N3A C8A 1.142(6) . ? N4A C9A 1.129(7) . ? C2A C3A 1.430(6) . ? C3A C6A 1.403(5) . ? C3A C4A 1.404(5) . ? C4A C7A 1.369(6) . ? C4A C5A 1.506(5) . ? C7A C8A 1.417(6) . ? C7A C9A 1.432(6) . ? O7 H7 0.86(2) . ? O7 H71 0.86(2) . ? 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 O4 176.5(2) . . ? O3 Cu1 N2 90.51(16) . . ? O4 Cu1 N2 88.83(16) . . ? O3 Cu1 N2A 89.19(16) . . ? O4 Cu1 N2A 91.55(17) . . ? N2 Cu1 N2A 178.62(17) . . ? Cu1 O3 H3 127(5) . . ? Cu1 O3 H31 114(5) . . ? H3 O3 H31 114(7) . . ? Cu1 O4 H4 128(4) . . ? Cu1 O4 H41 118(7) . . ? H4 O4 H41 113(7) . . ? H5 O5 H51 114(8) . . ? H6 O6 H61 107(6) . . ? C5 N1 C2 111.9(4) . . ? C5 N1 H1 124(4) . . ? C2 N1 H1 124(4) . . ? C6 N2 Cu1 175.4(4) . . ? O1 C2 N1 124.1(4) . . ? O1 C2 C3 128.4(4) . . ? N1 C2 C3 107.5(4) . . ? C6 C3 C4 128.8(4) . . ? C6 C3 C2 122.0(4) . . ? C4 C3 C2 109.2(3) . . ? C7 C4 C3 131.5(4) . . ? C7 C4 C5 122.5(4) . . ? C3 C4 C5 106.0(3) . . ? O2 C5 N1 126.9(4) . . ? O2 C5 C4 127.7(4) . . ? N1 C5 C4 105.4(3) . . ? N2 C6 C3 179.0(5) . . ? C4 C7 C8 119.5(3) . . ? C4 C7 C9 124.0(4) . . ? C8 C7 C9 116.4(4) . . ? N3 C8 C7 177.1(4) . . ? N4 C9 C7 175.9(5) . . ? C5A N1A C2A 111.9(3) . . ? C5A N1A H11 127(3) . . ? C2A N1A H11 121(3) . . ? C6A N2A Cu1 175.8(4) . . ? O1A C2A N1A 123.7(4) . . ? O1A C2A C3A 129.8(4) . . ? N1A C2A C3A 106.5(4) . . ? C6A C3A C4A 128.1(4) . . ? C6A C3A C2A 122.2(4) . . ? C4A C3A C2A 109.6(3) . . ? C7A C4A C3A 131.8(4) . . ? C7A C4A C5A 122.4(4) . . ? C3A C4A C5A 105.8(3) . . ? O2A C5A N1A 126.5(4) . . ? O2A C5A C4A 127.4(4) . . ? N1A C5A C4A 106.1(3) . . ? N2A C6A C3A 179.2(4) . . ? C4A C7A C8A 119.3(4) . . ? C4A C7A C9A 123.5(4) . . ? C8A C7A C9A 117.2(4) . . ? N3A C8A C7A 175.5(5) . . ? N4A C9A C7A 176.5(7) . . ? H7 O7 H71 103(8) . . ? 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 O4 H41 O6 0.75(8) 2.01(8) 2.768(5) 179(10) 2 O4 H4 N3A 0.69(5) 2.34(5) 3.008(6) 161(5) . O3 H31 O7 0.85(2) 1.72(3) 2.561(6) 168(8) . O3 H3 N3 0.71(5) 2.27(6) 2.961(6) 164(6) . N1 H1 O1A 0.77(5) 2.16(5) 2.911(5) 164(5) 1_554 N1A H11 O1 0.82(4) 2.00(4) 2.816(5) 171(4) 1_556 O7 H7 O1A 0.86(2) 2.12(4) 2.941(6) 162(9) . O6 H6 O1 0.71(6) 2.19(6) 2.890(5) 167(7) 2 O6 H61 O5 0.86(7) 2.20(7) 3.020(6) 158(6) 1_455 O7 H71 N4A 0.86(2) 2.19(7) 2.865(7) 135(8) 1_565 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 69.97 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.359 _refine_diff_density_min -0.599 _refine_diff_density_rms 0.069 data_cu3r _database_code_depnum_ccdc_archive 'CCDC 845140' #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; diacetonitrile(3-cyano-4-dicyanomethylene-5-oxo-4,5-dihydro-1H-pyrrol-2- olato)copper(I) ; _chemical_name_common ? _chemical_melting_point 380 _chemical_formula_moiety 'C12 H7 Cu N6 O2' _chemical_formula_sum 'C12 H7 Cu N6 O2' _chemical_formula_weight 330.78 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' Cu Cu -1.9646 0.5888 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.3101(7) _cell_length_b 15.741(1) _cell_length_c 8.5060(1) _cell_angle_alpha 90.00 _cell_angle_beta 105.20(1) _cell_angle_gamma 90.00 _cell_volume 686.11(10) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 31 _cell_measurement_theta_max 38 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_coefficient_mu 2.390 _exptl_absorpt_factor_muR 0.000 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.8854 _exptl_absorpt_correction_T_max 0.9988 _exptl_absorpt_correction_T_ave 0.9454 _exptl_absorpt_Rmerge_before 0.0325 _exptl_absorpt_Rmerge_after 0.0292 _exptl_absorpt_theta_corr_max 1.0000 _exptl_absorpt_theta_corr_min 0.9966 _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometr' _diffrn_measurement_method 'non-profiled omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% ? _diffrn_reflns_number 5512 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 5.39 _diffrn_reflns_theta_max 74.96 _reflns_number_total 2820 _reflns_number_gt 2665 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989' _computing_cell_refinement 'CAD-4 Software (Enraf-Nonius, 1989' _computing_data_reduction 'XCAD-4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2000; ' _computing_publication_material SHELXL-97 _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. ; _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^)+(0.0521P)^2^+0.0910P] 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 SHELXL _refine_ls_extinction_coef 0.0135(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 2820 _refine_ls_number_parameters 197 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0854 _refine_ls_wR_factor_gt 0.0836 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _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 Cu Cu 0.38328(6) 0.57852(3) 0.07261(4) 0.03967(13) Uani 1 1 d . . . O1 O 0.9344(5) 0.94684(16) -0.5255(3) 0.0548(5) Uani 1 1 d . . . O2 O 0.4628(4) 0.74775(16) -0.3385(3) 0.0577(6) Uani 1 1 d . . . N1 N 0.6509(5) 0.84689(16) -0.4701(3) 0.0446(5) Uani 1 1 d . . . N2 N 1.3844(5) 0.97855(16) -0.1291(3) 0.0455(5) Uani 1 1 d . . . N3 N 1.2600(6) 0.83147(19) 0.2007(3) 0.0583(7) Uani 1 1 d . . . N4 N 0.5848(5) 0.67609(16) 0.0246(3) 0.0446(5) Uani 1 1 d . . . N5 N 0.0650(5) 0.55574(17) -0.1041(3) 0.0497(6) Uani 1 1 d . . . N6 N 0.2422(5) 0.60794(16) 0.2642(3) 0.0464(5) Uani 1 1 d . . . C2 C 0.8681(5) 0.90023(19) -0.4303(3) 0.0399(6) Uani 1 1 d . . . C3 C 0.9885(5) 0.88706(16) -0.2570(3) 0.0337(5) Uani 1 1 d . . . C4 C 0.8502(5) 0.82688(16) -0.1968(3) 0.0318(5) Uani 1 1 d . . . C5 C 0.6271(5) 0.80023(17) -0.3390(3) 0.0399(5) Uani 1 1 d . . . C6 C 1.2085(5) 0.93553(16) -0.1802(3) 0.0360(5) Uani 1 1 d . . . C8 C 1.0936(6) 0.81500(17) 0.0913(3) 0.0405(6) Uani 1 1 d . . . C7 C 0.8809(5) 0.79132(16) -0.0438(3) 0.0345(5) Uani 1 1 d . . . C9 C 0.7125(5) 0.72796(16) -0.0104(3) 0.0372(5) Uani 1 1 d . . . C10 C -0.1328(5) 0.54458(19) -0.1906(3) 0.0405(5) Uani 1 1 d . . . C11 C -0.3896(6) 0.5323(2) -0.2992(4) 0.0511(7) Uani 1 1 d . . . H11A H -0.4920 0.4976 -0.2467 0.077 Uiso 1 1 calc R . . H11B H -0.3741 0.5048 -0.3970 0.077 Uiso 1 1 calc R . . H11C H -0.4731 0.5864 -0.3261 0.077 Uiso 1 1 calc R . . C12 C 0.1160(6) 0.62927(18) 0.3437(3) 0.0425(6) Uani 1 1 d . . . C13 C -0.0487(7) 0.6570(3) 0.4447(4) 0.0649(10) Uani 1 1 d . . . H13A H -0.0466 0.7179 0.4508 0.097 Uiso 1 1 calc R . . H13B H 0.0151 0.6337 0.5521 0.097 Uiso 1 1 calc R . . H13C H -0.2240 0.6377 0.3983 0.097 Uiso 1 1 calc R . . H1 H 0.547(8) 0.841(3) -0.563(5) 0.058(11) 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 Cu 0.03226(18) 0.0446(2) 0.04145(19) 0.00212(18) 0.00840(13) 0.00198(17) O1 0.0586(12) 0.0655(13) 0.0394(10) 0.0146(9) 0.0112(9) -0.0078(11) O2 0.0513(12) 0.0622(13) 0.0481(11) 0.0070(10) -0.0072(9) -0.0259(11) N1 0.0456(12) 0.0513(13) 0.0279(10) 0.0026(9) -0.0065(9) -0.0064(11) N2 0.0386(12) 0.0468(12) 0.0495(13) -0.0032(10) 0.0086(10) -0.0085(10) N3 0.0669(18) 0.0544(15) 0.0388(13) 0.0020(11) -0.0122(12) -0.0101(14) N4 0.0462(12) 0.0453(12) 0.0421(12) 0.0033(10) 0.0115(10) -0.0049(10) N5 0.0397(12) 0.0618(18) 0.0441(12) -0.0071(10) 0.0048(10) -0.0006(10) N6 0.0467(12) 0.0543(13) 0.0413(11) -0.0019(9) 0.0168(10) -0.0001(10) C2 0.0374(13) 0.0447(14) 0.0349(13) 0.0031(10) 0.0045(11) 0.0011(10) C3 0.0328(11) 0.0350(11) 0.0312(11) 0.0018(9) 0.0047(9) -0.0008(9) C4 0.0286(11) 0.0353(11) 0.0276(10) -0.0015(9) 0.0008(8) 0.0011(9) C5 0.0384(13) 0.0403(12) 0.0353(12) 0.0013(9) -0.0006(10) -0.0038(11) C6 0.0379(12) 0.0369(11) 0.0317(11) 0.0000(9) 0.0066(9) -0.0032(10) C8 0.0476(15) 0.0379(13) 0.0320(12) 0.0061(10) 0.0032(11) -0.0041(11) C7 0.0382(12) 0.0355(12) 0.0264(10) 0.0011(8) 0.0026(9) -0.0063(9) C9 0.0387(12) 0.0384(12) 0.0325(11) 0.0016(9) 0.0058(10) -0.0020(10) C10 0.0372(14) 0.0479(12) 0.0353(12) -0.0024(10) 0.0073(11) 0.0009(11) C11 0.0390(15) 0.0562(18) 0.0515(16) -0.0061(13) 0.0003(12) -0.0037(12) C12 0.0417(14) 0.0466(14) 0.0374(12) -0.0020(10) 0.0074(11) -0.0027(11) C13 0.0472(17) 0.097(3) 0.0554(18) -0.0188(19) 0.0219(15) -0.0049(18) _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 Cu N4 1.975(2) . ? Cu N5 1.978(3) . ? Cu N2 1.980(2) 2_745 ? Cu N6 2.018(2) . ? O1 C2 1.211(3) . ? O2 C5 1.202(3) . ? N1 C5 1.369(3) . ? N1 C2 1.395(3) . ? N1 H1 0.84(4) . ? N2 C6 1.143(4) . ? N2 Cu 1.980(2) 2_755 ? N3 C8 1.133(4) . ? N4 C9 1.150(4) . ? N5 C10 1.127(4) . ? N6 C12 1.121(4) . ? C2 C3 1.460(3) . ? C3 C4 1.377(4) . ? C3 C6 1.405(3) . ? C4 C7 1.387(3) . ? C4 C5 1.514(3) . ? C8 C7 1.433(3) . ? C7 C9 1.417(3) . ? C10 C11 1.445(4) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.444(4) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? 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 N4 Cu N5 112.67(11) . . ? N4 Cu N2 109.35(10) . 2_745 ? N5 Cu N2 113.22(11) . 2_745 ? N4 Cu N6 108.93(10) . . ? N5 Cu N6 103.36(11) . . ? N2 Cu N6 109.04(11) 2_745 . ? C5 N1 C2 111.8(2) . . ? C5 N1 H1 122(3) . . ? C2 N1 H1 127(3) . . ? C6 N2 Cu 163.4(2) . 2_755 ? C9 N4 Cu 174.0(2) . . ? C10 N5 Cu 171.4(2) . . ? C12 N6 Cu 164.4(3) . . ? O1 C2 N1 124.7(2) . . ? O1 C2 C3 129.4(3) . . ? N1 C2 C3 106.0(2) . . ? C4 C3 C6 131.4(2) . . ? C4 C3 C2 109.8(2) . . ? C6 C3 C2 118.9(2) . . ? C3 C4 C7 133.1(2) . . ? C3 C4 C5 106.0(2) . . ? C7 C4 C5 120.9(2) . . ? O2 C5 N1 126.4(2) . . ? O2 C5 C4 127.2(3) . . ? N1 C5 C4 106.4(2) . . ? N2 C6 C3 174.6(3) . . ? N3 C8 C7 177.8(3) . . ? C4 C7 C9 123.2(2) . . ? C4 C7 C8 121.4(2) . . ? C9 C7 C8 115.4(2) . . ? N4 C9 C7 176.4(3) . . ? N5 C10 C11 178.3(3) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N6 C12 C13 179.4(3) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 N1 H1 N3 0.84(4) 2.19(4) 3.027(3) 176(4) 1_454 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 74.96 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.236 _refine_diff_density_min -0.631 _refine_diff_density_rms 0.056 data_cu_x _database_code_depnum_ccdc_archive 'CCDC 845141' #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; acetonitrile(3-cyano-4-dicyanomethylene-5-oxo-4,5-dihydro-1H-pyrrol-2- olato)copper(I) ; _chemical_name_common ? _chemical_melting_point 390 _chemical_formula_moiety 'C10 H4 Cu N5 O2' _chemical_formula_sum 'C10 H4 Cu N5 O2' _chemical_formula_weight 289.72 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.378(2) _cell_length_b 8.246(3) _cell_length_c 9.217(2) _cell_angle_alpha 84.82(2) _cell_angle_beta 74.28(2) _cell_angle_gamma 88.30(2) _cell_volume 537.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13 _cell_measurement_theta_max 16 _exptl_crystal_description PLATE _exptl_crystal_colour RED _exptl_crystal_size_max .2 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.790 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 2.032 _exptl_absorpt_correction_type none _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 'Enraf-Nonius CAD-4 diffractometr' _diffrn_measurement_method 'non-profiled omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2746 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 27.96 _reflns_number_total 2586 _reflns_number_gt 2056 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989' _computing_cell_refinement 'CAD-4 Software (Enraf-Nonius, 1989' _computing_data_reduction 'XCAD-4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2000; ' _computing_publication_material SHELXL-97 _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. ; _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^)+(0.0427P)^2^+0.2160P] 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 2586 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0864 _refine_ls_wR_factor_gt 0.0792 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.002 _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 Cu1 Cu 0.16432(4) 0.68639(4) 0.64530(3) 0.03005(11) Uani 1 1 d . . . O1 O -0.0196(2) 0.8488(3) 0.1597(2) 0.0395(5) Uani 1 1 d . . . O2 O 0.5447(2) 0.9101(2) -0.1960(2) 0.0338(4) Uani 1 1 d . . . N1 N 0.2395(3) 0.9019(3) -0.0442(2) 0.0290(4) Uani 1 1 d . . . N2 N 0.2023(3) 0.6223(3) 0.4313(2) 0.0310(4) Uani 1 1 d . . . N3 N 0.6919(3) 0.4576(3) 0.2383(2) 0.0316(5) Uani 1 1 d . . . N4 N 0.9156(3) 0.6856(3) -0.2009(2) 0.0346(5) Uani 1 1 d . . . C2 C 0.1468(3) 0.8302(3) 0.0981(3) 0.0265(5) Uani 1 1 d . . . C3 C 0.2864(3) 0.7314(3) 0.1530(2) 0.0227(4) Uani 1 1 d . . . C4 C 0.4562(3) 0.7397(2) 0.0425(2) 0.0201(4) Uani 1 1 d . . . C5 C 0.4264(3) 0.8593(3) -0.0847(2) 0.0226(4) Uani 1 1 d . . . C6 C 0.2437(3) 0.6644(3) 0.3047(3) 0.0239(4) Uani 1 1 d . . . C7 C 0.6301(3) 0.6642(3) 0.0318(2) 0.0224(4) Uani 1 1 d . . . C8 C 0.6612(3) 0.5511(3) 0.1485(3) 0.0241(4) Uani 1 1 d . . . C9 C 0.7855(3) 0.6830(3) -0.0995(3) 0.0253(5) Uani 1 1 d . . . N5 N 0.2417(3) 0.9204(3) 0.5878(3) 0.0391(5) Uani 1 1 d . . . C10 C 0.2661(4) 1.0546(3) 0.5541(3) 0.0327(5) Uani 1 1 d . . . C11 C 0.2956(4) 1.2278(3) 0.5143(3) 0.0411(6) Uani 1 1 d . . . H11A H 0.2162 1.2873 0.5925 0.062 Uiso 1 1 calc R . . H11B H 0.2652 1.2578 0.4205 0.062 Uiso 1 1 calc R . . H11C H 0.4250 1.2531 0.5034 0.062 Uiso 1 1 calc R . . H1 H 0.194(5) 0.972(4) -0.091(4) 0.049(10) 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 Cu1 0.02966(16) 0.03392(18) 0.02173(16) 0.00581(11) -0.00191(11) 0.00527(11) O1 0.0253(9) 0.0534(12) 0.0314(9) 0.0077(8) 0.0012(7) 0.0175(8) O2 0.0313(9) 0.0382(10) 0.0260(9) 0.0096(7) -0.0017(7) 0.0014(7) N1 0.0270(10) 0.0355(11) 0.0209(9) 0.0055(8) -0.0042(8) 0.0114(8) N2 0.0327(10) 0.0349(11) 0.0221(10) 0.0023(8) -0.0038(8) 0.0049(9) N3 0.0295(10) 0.0354(11) 0.0280(10) 0.0027(9) -0.0074(8) 0.0083(8) N4 0.0258(10) 0.0446(13) 0.0280(11) 0.0053(9) -0.0012(8) 0.0054(9) C2 0.0260(11) 0.0299(11) 0.0213(11) 0.0016(9) -0.0046(8) 0.0093(9) C3 0.0232(10) 0.0247(10) 0.0182(10) 0.0010(8) -0.0039(8) 0.0067(8) C4 0.0232(10) 0.0188(10) 0.0182(10) -0.0014(8) -0.0059(8) 0.0026(8) C5 0.0247(10) 0.0226(10) 0.0198(10) -0.0002(8) -0.0058(8) 0.0033(8) C6 0.0221(10) 0.0229(10) 0.0244(11) 0.0002(8) -0.0038(8) 0.0047(8) C7 0.0200(10) 0.0250(11) 0.0203(10) 0.0013(8) -0.0033(8) 0.0028(8) C8 0.0208(10) 0.0258(11) 0.0250(11) -0.0016(9) -0.0055(8) 0.0055(8) C9 0.0216(10) 0.0276(11) 0.0248(11) 0.0008(9) -0.0044(9) 0.0038(8) N5 0.0437(13) 0.0315(12) 0.0364(12) 0.0017(9) -0.0028(10) 0.0025(10) C10 0.0339(13) 0.0332(14) 0.0274(12) -0.0010(10) -0.0028(10) 0.0039(10) C11 0.0487(16) 0.0298(13) 0.0361(14) 0.0000(11) 0.0026(12) -0.0002(12) _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 Cu1 N4 1.992(2) 1_456 ? Cu1 N3 2.000(2) 2_666 ? Cu1 N5 2.011(2) . ? Cu1 N2 2.032(2) . ? O1 C2 1.217(3) . ? O2 C5 1.203(3) . ? N1 C5 1.371(3) . ? N1 C2 1.391(3) . ? N1 H1 0.80(4) . ? N2 C6 1.146(3) . ? N3 C8 1.143(3) . ? N3 Cu1 2.000(2) 2_666 ? N4 C9 1.143(3) . ? N4 Cu1 1.992(2) 1_654 ? C2 C3 1.462(3) . ? C3 C4 1.383(3) . ? C3 C6 1.412(3) . ? C4 C7 1.392(3) . ? C4 C5 1.521(3) . ? C7 C8 1.421(3) . ? C7 C9 1.425(3) . ? N5 C10 1.129(3) . ? C10 C11 1.450(4) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? 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 N4 Cu1 N3 99.13(9) 1_456 2_666 ? N4 Cu1 N5 107.24(10) 1_456 . ? N3 Cu1 N5 119.10(10) 2_666 . ? N4 Cu1 N2 123.88(10) 1_456 . ? N3 Cu1 N2 112.33(9) 2_666 . ? N5 Cu1 N2 96.60(10) . . ? C5 N1 C2 111.67(19) . . ? C5 N1 H1 123(2) . . ? C2 N1 H1 124(3) . . ? C6 N2 Cu1 146.5(2) . . ? C8 N3 Cu1 160.3(2) . 2_666 ? C9 N4 Cu1 171.4(2) . 1_654 ? O1 C2 N1 124.5(2) . . ? O1 C2 C3 128.7(2) . . ? N1 C2 C3 106.80(19) . . ? C4 C3 C6 130.1(2) . . ? C4 C3 C2 108.95(19) . . ? C6 C3 C2 120.3(2) . . ? C3 C4 C7 133.0(2) . . ? C3 C4 C5 106.22(18) . . ? C7 C4 C5 120.77(19) . . ? O2 C5 N1 127.1(2) . . ? O2 C5 C4 126.7(2) . . ? N1 C5 C4 106.17(18) . . ? N2 C6 C3 174.3(2) . . ? C4 C7 C8 121.9(2) . . ? C4 C7 C9 123.5(2) . . ? C8 C7 C9 114.46(19) . . ? N3 C8 C7 177.3(2) . . ? N4 C9 C7 174.2(2) . . ? C10 N5 Cu1 172.6(2) . . ? N5 C10 C11 178.7(3) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 N1 H1 O1 0.80(4) 2.10(4) 2.887(3) 165(3) 2_575 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.96 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.384 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.077