# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Stuart Batten' 'Sze Nee Pek.' 'David Turner' _publ_contact_author_name 'Stuart Batten' _publ_contact_author_email STUART.BATTEN@SCI.MONASH.EDU.AU _publ_section_title ; 2C or not 2C: The C2 Difference Between 2,2'-Bipyridine and 1,10-Phenanthroline Changes Bridging Species in [Cu(cdm)Cl(L)]2 Dimers ; # Attachment '2C_CIF.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 698651' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [Cu(2,2'-bipy)(cdm)Cl]2.2MeOH ; _chemical_name_common "[Cu(2,2'-bipy)(cdm)Cl]2.2MeOH" _chemical_melting_point ? _chemical_formula_moiety 'C28 H20 Cl2 Cu2 N10 O2, 2(C H4 O)' _chemical_formula_sum 'C30 H28 Cl2 Cu2 N10 O4' _chemical_formula_weight 790.60 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3016(8) _cell_length_b 8.8946(9) _cell_length_c 11.7703(13) _cell_angle_alpha 83.191(3) _cell_angle_beta 81.216(3) _cell_angle_gamma 67.746(3) _cell_volume 793.19(14) _cell_formula_units_Z 1 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 5658 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 27.50 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.655 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 402 _exptl_absorpt_coefficient_mu 1.564 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7348 _exptl_absorpt_correction_T_max 0.9259 _exptl_absorpt_process_details SADABS _exptl_special_details ; OH and NH protons located from Fourier map ; _diffrn_ambient_temperature 123(1) _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 'Bruker X8 Apex II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5658 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0659 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3610 _reflns_number_gt 2882 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker)' _computing_cell_refinement 'Bruker SMART (Bruker)' _computing_data_reduction 'Bruker SAINT (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.2000P)^2^+0.0000P] 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 3610 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 0.21607(4) 0.99350(4) -0.00694(3) 0.01436(12) Uani 1 1 d . . . Cl1 Cl 0.02824(9) 0.80725(8) 0.06880(7) 0.01595(17) Uani 1 1 d . . . O1 O 0.4090(3) 0.9962(2) 0.3684(2) 0.0197(5) Uani 1 1 d . . . N1 N 0.2911(4) 1.1877(3) 0.4986(3) 0.0211(6) Uani 1 1 d . . . C1 C 0.1600(4) 1.2226(4) 0.3244(3) 0.0166(7) Uani 1 1 d . . . H1N H 0.224(4) 1.279(4) 0.525(3) 0.024(10) Uiso 1 1 d . . . H1O H 0.385(5) 0.785(5) 0.382(4) 0.043(13) Uiso 1 1 d . . . O2 O 0.3592(3) 0.6995(3) 0.3935(2) 0.0292(6) Uani 1 1 d . . . N2 N 0.1818(3) 1.1030(3) 0.1349(3) 0.0184(6) Uani 1 1 d . . . C2 C 0.1695(4) 1.1589(4) 0.2200(3) 0.0170(7) Uani 1 1 d . . . H2N H 0.373(5) 1.136(5) 0.542(4) 0.040(12) Uiso 1 1 d . . . N3 N -0.0761(4) 1.4982(3) 0.3757(3) 0.0275(7) Uani 1 1 d . . . C3 C 0.0281(4) 1.3750(4) 0.3509(3) 0.0187(7) Uani 1 1 d . . . N4 N 0.4458(3) 0.8224(3) 0.0328(2) 0.0147(5) Uani 1 1 d . . . C4 C 0.2939(4) 1.1294(4) 0.3989(3) 0.0173(7) Uani 1 1 d . . . N5 N 0.2955(3) 0.8843(3) -0.1554(2) 0.0161(6) Uani 1 1 d . . . C5 C 0.5189(4) 0.8075(4) 0.1295(3) 0.0172(7) Uani 1 1 d . . . H5 H 0.4640 0.8868 0.1847 0.021 Uiso 1 1 calc R . . C6 C 0.6731(4) 0.6788(4) 0.1510(3) 0.0205(7) Uani 1 1 d . . . H6 H 0.7229 0.6698 0.2202 0.025 Uiso 1 1 calc R . . C7 C 0.7524(4) 0.5645(4) 0.0704(3) 0.0209(7) Uani 1 1 d . . . H7 H 0.8575 0.4754 0.0837 0.025 Uiso 1 1 calc R . . C8 C 0.6789(4) 0.5802(4) -0.0292(3) 0.0189(7) Uani 1 1 d . . . H8 H 0.7325 0.5023 -0.0855 0.023 Uiso 1 1 calc R . . C9 C 0.5243(4) 0.7119(4) -0.0466(3) 0.0161(7) Uani 1 1 d . . . C10 C 0.4374(4) 0.7430(4) -0.1513(3) 0.0164(7) Uani 1 1 d . . . C11 C 0.4900(4) 0.6399(4) -0.2403(3) 0.0203(7) Uani 1 1 d . . . H11 H 0.5871 0.5399 -0.2352 0.024 Uiso 1 1 calc R . . C12 C 0.4019(4) 0.6820(4) -0.3359(3) 0.0229(7) Uani 1 1 d . . . H12 H 0.4362 0.6115 -0.3971 0.028 Uiso 1 1 calc R . . C13 C 0.2616(4) 0.8297(4) -0.3415(3) 0.0219(7) Uani 1 1 d . . . H13 H 0.2007 0.8637 -0.4077 0.026 Uiso 1 1 calc R . . C14 C 0.2128(4) 0.9256(4) -0.2496(3) 0.0189(7) Uani 1 1 d . . . H14 H 0.1159 1.0258 -0.2533 0.023 Uiso 1 1 calc R . . C15 C 0.1864(5) 0.7434(5) 0.3669(4) 0.0341(9) Uani 1 1 d . . . H15A H 0.1479 0.6513 0.3881 0.051 Uiso 1 1 calc R . . H15B H 0.1830 0.7725 0.2841 0.051 Uiso 1 1 calc R . . H15C H 0.1082 0.8368 0.4101 0.051 Uiso 1 1 calc R . . 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 0.01125(18) 0.01189(19) 0.0196(2) -0.00392(15) -0.00382(15) -0.00226(13) Cl1 0.0135(3) 0.0121(3) 0.0219(4) -0.0025(3) -0.0044(3) -0.0031(3) O1 0.0160(10) 0.0144(11) 0.0278(14) -0.0065(10) -0.0067(10) -0.0017(8) N1 0.0195(14) 0.0162(14) 0.0249(17) -0.0069(13) -0.0067(13) -0.0003(11) C1 0.0154(14) 0.0160(15) 0.0205(18) -0.0035(13) -0.0064(13) -0.0057(11) O2 0.0304(13) 0.0219(13) 0.0356(17) -0.0009(12) -0.0097(12) -0.0083(11) N2 0.0194(13) 0.0143(13) 0.0222(16) -0.0036(12) -0.0102(12) -0.0032(10) C2 0.0101(13) 0.0122(14) 0.029(2) 0.0008(14) -0.0061(13) -0.0036(11) N3 0.0268(15) 0.0209(15) 0.0317(19) -0.0088(13) -0.0123(14) -0.0001(12) C3 0.0179(14) 0.0195(16) 0.0211(18) -0.0007(14) -0.0092(13) -0.0072(12) N4 0.0145(12) 0.0121(12) 0.0196(15) -0.0049(11) -0.0020(11) -0.0061(9) C4 0.0150(14) 0.0160(15) 0.0239(19) 0.0000(13) -0.0043(13) -0.0087(11) N5 0.0147(12) 0.0141(12) 0.0211(15) -0.0035(11) -0.0036(11) -0.0059(10) C5 0.0143(13) 0.0169(15) 0.0211(18) -0.0027(13) -0.0038(13) -0.0055(11) C6 0.0188(15) 0.0218(16) 0.0237(19) 0.0005(14) -0.0079(14) -0.0092(12) C7 0.0142(14) 0.0145(15) 0.032(2) -0.0008(14) -0.0030(14) -0.0035(12) C8 0.0164(14) 0.0128(15) 0.0259(19) -0.0045(13) -0.0007(14) -0.0034(11) C9 0.0146(13) 0.0126(14) 0.0234(18) -0.0013(13) 0.0005(13) -0.0084(11) C10 0.0167(14) 0.0119(14) 0.0227(18) -0.0038(13) 0.0007(13) -0.0080(11) C11 0.0194(15) 0.0162(15) 0.0256(19) -0.0059(14) 0.0011(14) -0.0070(12) C12 0.0263(16) 0.0177(16) 0.028(2) -0.0078(15) 0.0009(15) -0.0113(13) C13 0.0219(15) 0.0278(18) 0.0198(19) -0.0031(15) -0.0041(14) -0.0126(13) C14 0.0179(14) 0.0188(16) 0.0201(18) -0.0033(14) -0.0023(13) -0.0063(12) C15 0.0303(19) 0.044(2) 0.034(2) -0.0031(19) -0.0084(17) -0.0188(17) _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 1.962(3) . ? Cu1 N5 1.999(3) . ? Cu1 N4 2.019(2) . ? Cu1 Cl1 2.2819(8) 2_575 ? Cu1 Cl1 2.6743(8) . ? Cl1 Cu1 2.2819(8) 2_575 ? O1 C4 1.259(4) . ? N1 C4 1.331(4) . ? N1 H1N 0.86(4) . ? N1 H2N 0.87(4) . ? C1 C2 1.392(5) . ? C1 C3 1.417(4) . ? C1 C4 1.455(4) . ? O2 C15 1.411(4) . ? O2 H1O 0.86(4) . ? N2 C2 1.145(4) . ? N3 C3 1.147(4) . ? N4 C5 1.340(4) . ? N4 C9 1.347(4) . ? N5 C14 1.335(4) . ? N5 C10 1.360(4) . ? C5 C6 1.391(4) . ? C5 H5 0.9500 . ? C6 C7 1.377(5) . ? C6 H6 0.9500 . ? C7 C8 1.372(5) . ? C7 H7 0.9500 . ? C8 C9 1.395(4) . ? C8 H8 0.9500 . ? C9 C10 1.468(5) . ? C10 C11 1.383(5) . ? C11 C12 1.373(5) . ? C11 H11 0.9500 . ? C12 C13 1.389(4) . ? C12 H12 0.9500 . ? C13 C14 1.372(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 N5 169.27(10) . . ? N2 Cu1 N4 92.25(11) . . ? N5 Cu1 N4 80.94(11) . . ? N2 Cu1 Cl1 90.91(7) . 2_575 ? N5 Cu1 Cl1 95.21(7) . 2_575 ? N4 Cu1 Cl1 174.19(8) . 2_575 ? N2 Cu1 Cl1 98.10(8) . . ? N5 Cu1 Cl1 90.76(7) . . ? N4 Cu1 Cl1 94.66(7) . . ? Cl1 Cu1 Cl1 89.71(3) 2_575 . ? Cu1 Cl1 Cu1 90.29(3) 2_575 . ? C4 N1 H1N 129(3) . . ? C4 N1 H2N 120(3) . . ? H1N N1 H2N 111(4) . . ? C2 C1 C3 119.5(3) . . ? C2 C1 C4 117.0(3) . . ? C3 C1 C4 123.4(3) . . ? C15 O2 H1O 107(3) . . ? C2 N2 Cu1 176.0(2) . . ? N2 C2 C1 178.0(3) . . ? N3 C3 C1 177.6(4) . . ? C5 N4 C9 119.5(3) . . ? C5 N4 Cu1 126.5(2) . . ? C9 N4 Cu1 113.9(2) . . ? O1 C4 N1 121.4(3) . . ? O1 C4 C1 119.7(3) . . ? N1 C4 C1 118.8(3) . . ? C14 N5 C10 118.6(3) . . ? C14 N5 Cu1 126.7(2) . . ? C10 N5 Cu1 114.1(2) . . ? N4 C5 C6 121.6(3) . . ? N4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C7 C6 C5 118.9(3) . . ? C7 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C8 C7 C6 119.6(3) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 119.1(3) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? N4 C9 C8 121.2(3) . . ? N4 C9 C10 115.2(3) . . ? C8 C9 C10 123.7(3) . . ? N5 C10 C11 120.9(3) . . ? N5 C10 C9 114.6(3) . . ? C11 C10 C9 124.5(3) . . ? C12 C11 C10 120.0(3) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 118.8(3) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C14 C13 C12 118.7(3) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? N5 C14 C13 122.9(3) . . ? N5 C14 H14 118.5 . . ? C13 C14 H14 118.5 . . ? O2 C15 H15A 109.5 . . ? O2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 H1N N3 0.86(4) 2.25(4) 3.094(4) 169(3) 2_586 O2 H1O O1 0.86(4) 1.95(4) 2.799(3) 172(4) . C5 H5 O1 0.95 2.39 3.276(4) 156.0 . N1 H2N O1 0.87(4) 2.11(4) 2.970(4) 174(4) 2_676 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.664 _refine_diff_density_min -0.954 _refine_diff_density_rms 0.105 data_2 _database_code_depnum_ccdc_archive 'CCDC 698652' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [(carbamoyldicyanomethanide)(chloro)(1,10-phenanthroline)copper(II)] methanol solvate ; _chemical_name_common '[Cu(cdm)Cl(1,10-phen)]2.2MeOH' _chemical_melting_point ? _chemical_formula_moiety 'C32 H20 Cl2 Cu2 N10 O2, 2(C H4 O)' _chemical_formula_sum 'C34 H28 Cl2 Cu2 N10 O4' _chemical_formula_weight 838.64 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4044(7) _cell_length_b 9.9340(9) _cell_length_c 12.0617(13) _cell_angle_alpha 108.736(5) _cell_angle_beta 91.509(5) _cell_angle_gamma 99.329(5) _cell_volume 826.15(14) _cell_formula_units_Z 1 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 4985 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 25.00 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.686 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 426 _exptl_absorpt_coefficient_mu 1.507 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7328 _exptl_absorpt_correction_T_max 0.9150 _exptl_absorpt_process_details SADABS _exptl_special_details ; OH and NH protons located experimentally ; _diffrn_ambient_temperature 123(1) _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 'Bruker X8 Apex II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4985 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2864 _reflns_number_gt 2465 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker)' _computing_cell_refinement 'Bruker SMART (Bruker)' _computing_data_reduction 'Bruker SAINT (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.2000P)^2^+0.0000P] 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 2864 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0717 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.013 _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 0.57927(5) 0.66570(4) 0.80510(3) 0.01211(12) Uani 1 1 d . . . Cl1 Cl 0.49885(11) 0.87839(7) 0.82208(7) 0.0253(2) Uani 1 1 d . . . O1 O 0.0664(3) 0.7194(2) 0.40236(18) 0.0215(5) Uani 1 1 d . . . N1 N 0.2163(4) 0.8313(3) 0.5822(2) 0.0185(6) Uani 1 1 d . . . C1 C 0.2213(4) 0.5801(3) 0.4834(3) 0.0127(6) Uani 1 1 d . . . H1N H 0.195(4) 0.913(4) 0.582(3) 0.025(9) Uiso 1 1 d . . . H1O H -0.134(4) 0.839(3) 0.430(3) 0.010(9) Uiso 1 1 d . . . O2 O -0.2030(3) 0.8835(2) 0.43693(19) 0.0200(5) Uani 1 1 d . . . N2 N 0.4120(3) 0.5789(2) 0.6614(2) 0.0167(5) Uani 1 1 d . . . C2 C 0.3255(4) 0.5733(3) 0.5783(3) 0.0133(6) Uani 1 1 d . . . H2N H 0.283(5) 0.831(4) 0.639(3) 0.030(10) Uiso 1 1 d . . . N3 N 0.1481(3) 0.3565(3) 0.2998(2) 0.0177(5) Uani 1 1 d . . . C3 C 0.1762(4) 0.4572(3) 0.3831(3) 0.0141(6) Uani 1 1 d . . . N4 N 0.5921(3) 0.4757(2) 0.8280(2) 0.0113(5) Uani 1 1 d . . . C4 C 0.1630(4) 0.7146(3) 0.4868(3) 0.0152(6) Uani 1 1 d . . . N5 N 0.7279(3) 0.7435(2) 0.9614(2) 0.0123(5) Uani 1 1 d . . . C5 C 0.5239(4) 0.3432(3) 0.7574(3) 0.0143(6) Uani 1 1 d . . . H5 H 0.4584 0.3310 0.6850 0.017 Uiso 1 1 calc R . . C6 C 0.5453(4) 0.2210(3) 0.7861(3) 0.0155(6) Uani 1 1 d . . . H6 H 0.4953 0.1272 0.7337 0.019 Uiso 1 1 calc R . . C7 C 0.6388(4) 0.2372(3) 0.8902(3) 0.0158(6) Uani 1 1 d . . . H7 H 0.6530 0.1545 0.9106 0.019 Uiso 1 1 calc R . . C8 C 0.7138(4) 0.3757(3) 0.9668(3) 0.0136(6) Uani 1 1 d . . . C9 C 0.8152(4) 0.4061(3) 1.0774(3) 0.0152(6) Uani 1 1 d . . . H9 H 0.8329 0.3283 1.1036 0.018 Uiso 1 1 calc R . . C10 C 0.8859(4) 0.5422(3) 1.1452(3) 0.0156(6) Uani 1 1 d . . . H10 H 0.9532 0.5584 1.2178 0.019 Uiso 1 1 calc R . . C11 C 0.8617(3) 0.6634(3) 1.1098(2) 0.0127(6) Uani 1 1 d . . . C12 C 0.9346(4) 0.8086(3) 1.1743(3) 0.0159(6) Uani 1 1 d . . . H12 H 1.0063 0.8323 1.2467 0.019 Uiso 1 1 calc R . . C13 C 0.9015(4) 0.9153(3) 1.1319(3) 0.0162(6) Uani 1 1 d . . . H13 H 0.9496 1.0136 1.1750 0.019 Uiso 1 1 calc R . . C14 C 0.7967(4) 0.8789(3) 1.0252(3) 0.0140(6) Uani 1 1 d . . . H1 H 0.7738 0.9543 0.9972 0.017 Uiso 1 1 calc R . . C15 C 0.7609(3) 0.6366(3) 1.0028(2) 0.0117(6) Uani 1 1 d . . . C16 C 0.6866(3) 0.4919(3) 0.9307(2) 0.0107(6) Uani 1 1 d . . . C17 C -0.2770(5) 0.8871(4) 0.5453(3) 0.0291(8) Uani 1 1 d . . . H17A H -0.1766 0.9071 0.6061 0.044 Uiso 1 1 calc R . . H17B H -0.3541 0.7936 0.5361 0.044 Uiso 1 1 calc R . . H17C H -0.3514 0.9632 0.5683 0.044 Uiso 1 1 calc R . . 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 0.01522(19) 0.01074(18) 0.0107(2) 0.00422(14) -0.00286(13) 0.00248(13) Cl1 0.0391(5) 0.0120(4) 0.0234(4) 0.0038(3) -0.0133(3) 0.0076(3) O1 0.0271(12) 0.0242(11) 0.0148(12) 0.0065(10) -0.0073(9) 0.0107(9) N1 0.0221(14) 0.0175(14) 0.0166(15) 0.0055(12) -0.0059(12) 0.0071(11) C1 0.0111(13) 0.0140(14) 0.0132(15) 0.0047(12) -0.0006(11) 0.0025(11) O2 0.0225(12) 0.0220(12) 0.0205(13) 0.0098(10) 0.0032(10) 0.0122(10) N2 0.0193(13) 0.0126(12) 0.0179(15) 0.0038(11) -0.0028(11) 0.0049(10) C2 0.0105(14) 0.0104(14) 0.0188(17) 0.0047(13) 0.0013(13) 0.0012(11) N3 0.0215(13) 0.0203(14) 0.0135(14) 0.0078(12) 0.0012(11) 0.0054(11) C3 0.0114(14) 0.0203(16) 0.0168(17) 0.0132(15) 0.0026(12) 0.0055(12) N4 0.0093(11) 0.0133(12) 0.0120(13) 0.0049(10) 0.0008(9) 0.0023(9) C4 0.0146(14) 0.0210(16) 0.0129(16) 0.0078(13) 0.0041(12) 0.0062(12) N5 0.0117(11) 0.0138(12) 0.0125(13) 0.0056(10) 0.0008(10) 0.0027(9) C5 0.0127(14) 0.0150(14) 0.0150(16) 0.0055(13) -0.0002(12) 0.0013(11) C6 0.0145(14) 0.0104(14) 0.0205(17) 0.0038(12) 0.0027(12) 0.0017(11) C7 0.0130(14) 0.0151(15) 0.0244(18) 0.0118(13) 0.0050(12) 0.0050(11) C8 0.0101(13) 0.0169(14) 0.0161(16) 0.0069(13) 0.0038(12) 0.0049(11) C9 0.0125(14) 0.0203(15) 0.0187(16) 0.0123(13) 0.0012(12) 0.0071(12) C10 0.0121(14) 0.0259(16) 0.0129(16) 0.0100(13) 0.0009(12) 0.0072(12) C11 0.0078(13) 0.0199(15) 0.0109(15) 0.0044(12) 0.0022(11) 0.0050(11) C12 0.0110(14) 0.0239(16) 0.0107(16) 0.0031(13) -0.0009(12) 0.0030(12) C13 0.0170(15) 0.0142(15) 0.0133(16) 0.0004(12) 0.0000(12) 0.0003(12) C14 0.0165(14) 0.0119(14) 0.0144(16) 0.0056(12) 0.0016(12) 0.0018(11) C15 0.0081(13) 0.0153(14) 0.0131(15) 0.0064(12) 0.0044(11) 0.0024(11) C16 0.0057(12) 0.0150(14) 0.0129(15) 0.0062(12) 0.0028(11) 0.0023(10) C17 0.0281(18) 0.036(2) 0.0259(19) 0.0122(16) 0.0058(15) 0.0079(15) _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 1.965(3) . ? Cu1 N4 2.010(2) . ? Cu1 N5 2.010(2) . ? Cu1 Cl1 2.2354(8) . ? Cu1 N3 2.413(2) 2_666 ? O1 C4 1.247(3) . ? N1 C4 1.340(4) . ? N1 H1N 0.86(3) . ? N1 H2N 0.83(4) . ? C1 C2 1.389(4) . ? C1 C3 1.401(4) . ? C1 C4 1.459(4) . ? O2 C17 1.423(4) . ? O2 H1O 0.72(3) . ? N2 C2 1.156(4) . ? N3 C3 1.153(4) . ? N3 Cu1 2.413(2) 2_666 ? N4 C5 1.324(4) . ? N4 C16 1.357(4) . ? N5 C14 1.324(4) . ? N5 C15 1.361(3) . ? C5 C6 1.396(4) . ? C5 H5 0.9500 . ? C6 C7 1.368(4) . ? C6 H6 0.9500 . ? C7 C8 1.401(4) . ? C7 H7 0.9500 . ? C8 C16 1.398(4) . ? C8 C9 1.432(4) . ? C9 C10 1.344(4) . ? C9 H9 0.9500 . ? C10 C11 1.435(4) . ? C10 H10 0.9500 . ? C11 C15 1.400(4) . ? C11 C12 1.408(4) . ? C12 C13 1.367(4) . ? C12 H12 0.9500 . ? C13 C14 1.396(4) . ? C13 H13 0.9500 . ? C14 H1 0.9500 . ? C15 C16 1.429(4) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? 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 N4 94.29(10) . . ? N2 Cu1 N5 173.30(10) . . ? N4 Cu1 N5 82.14(9) . . ? N2 Cu1 Cl1 88.51(7) . . ? N4 Cu1 Cl1 161.56(7) . . ? N5 Cu1 Cl1 93.13(7) . . ? N2 Cu1 N3 93.65(9) . 2_666 ? N4 Cu1 N3 88.58(8) . 2_666 ? N5 Cu1 N3 91.93(9) . 2_666 ? Cl1 Cu1 N3 109.46(6) . 2_666 ? C4 N1 H1N 119(2) . . ? C4 N1 H2N 123(2) . . ? H1N N1 H2N 117(3) . . ? C2 C1 C3 119.4(2) . . ? C2 C1 C4 120.5(3) . . ? C3 C1 C4 120.1(3) . . ? C17 O2 H1O 106(3) . . ? C2 N2 Cu1 158.1(2) . . ? N2 C2 C1 174.7(3) . . ? C3 N3 Cu1 110.2(2) . 2_666 ? N3 C3 C1 176.7(3) . . ? C5 N4 C16 118.5(2) . . ? C5 N4 Cu1 128.93(19) . . ? C16 N4 Cu1 112.53(18) . . ? O1 C4 N1 121.5(3) . . ? O1 C4 C1 120.2(3) . . ? N1 C4 C1 118.2(3) . . ? C14 N5 C15 118.2(2) . . ? C14 N5 Cu1 129.50(19) . . ? C15 N5 Cu1 112.33(18) . . ? N4 C5 C6 122.0(3) . . ? N4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C7 C6 C5 119.5(3) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 120.0(3) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C16 C8 C7 116.6(3) . . ? C16 C8 C9 118.3(3) . . ? C7 C8 C9 125.1(3) . . ? C10 C9 C8 121.6(3) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C9 C10 C11 121.3(3) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C15 C11 C12 117.0(3) . . ? C15 C11 C10 118.3(3) . . ? C12 C11 C10 124.7(3) . . ? C13 C12 C11 119.5(3) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 119.7(3) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? N5 C14 C13 122.5(3) . . ? N5 C14 H1 118.8 . . ? C13 C14 H1 118.8 . . ? N5 C15 C11 123.1(3) . . ? N5 C15 C16 116.5(2) . . ? C11 C15 C16 120.4(2) . . ? N4 C16 C8 123.3(3) . . ? N4 C16 C15 116.5(2) . . ? C8 C16 C15 120.2(3) . . ? O2 C17 H17A 109.5 . . ? O2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 H1N O2 0.86(3) 2.09(4) 2.932(4) 166(3) 2_576 O2 H1O O1 0.72(3) 2.02(3) 2.733(3) 177(3) . N1 H2N Cl1 0.83(4) 2.56(4) 3.386(3) 170(3) . _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.355 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.075 data_3 _database_code_depnum_ccdc_archive 'CCDC 698653' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [Cu(cdm)(acac)(H2O)]2.4H2O ; _chemical_name_common '[Cu(cdm)(acac)(H2O)]2.4H2O' _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 Cu2 N6 O8, 4(H2 O)' _chemical_formula_sum 'C18 H30 Cu2 N6 O12' _chemical_formula_weight 649.56 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' Cu Cu 0.3201 1.2651 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1154(10) _cell_length_b 8.9932(9) _cell_length_c 11.1540(11) _cell_angle_alpha 113.154(6) _cell_angle_beta 101.507(6) _cell_angle_gamma 101.847(6) _cell_volume 696.12(13) _cell_formula_units_Z 1 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 5208 _cell_measurement_theta_min 2.09 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 334 _exptl_absorpt_coefficient_mu 1.594 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7411 _exptl_absorpt_correction_T_max 0.9246 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _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 'Bruker X8 Apex II CCD' _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_% ? _diffrn_reflns_number 5208 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3042 _reflns_number_gt 2607 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker)' _computing_cell_refinement 'Bruker SMART (Bruker)' _computing_data_reduction 'Bruker SAINT (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.2000P)^2^+0.0000P] 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_extinction_expression ? _refine_ls_number_reflns 3042 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1105 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 0.26136(5) 0.42103(4) 0.07985(4) 0.01908(13) Uani 1 1 d . . . O1 O 0.3034(3) -0.1184(3) 0.3562(2) 0.0247(5) Uani 1 1 d . . . O2 O 0.2454(3) 0.5455(3) -0.0268(2) 0.0212(5) Uani 1 1 d . . . O3 O 0.4858(3) 0.5778(3) 0.2084(2) 0.0216(5) Uani 1 1 d . . . O4 O 0.0997(4) 0.5461(3) 0.2113(3) 0.0229(5) Uani 1 1 d . . . O5 O 0.9276(7) 0.5857(8) 0.5902(5) 0.122(2) Uani 1 1 d . . . O6 O 0.6014(6) 0.4823(4) 0.4224(4) 0.0791(13) Uani 1 1 d . . . N1 N 0.4896(4) 0.1386(3) 0.4118(3) 0.0287(6) Uani 1 1 d . . . H1A H 0.5628 0.1372 0.4808 0.034 Uiso 1 1 calc R . . H1B H 0.5140 0.2264 0.3941 0.034 Uiso 1 1 calc R . . N2 N 0.2790(4) 0.2627(3) 0.1617(3) 0.0248(6) Uani 1 1 d . . . N3 N -0.0513(4) -0.2360(3) 0.0651(3) 0.0227(6) Uani 1 1 d . . . C1 C 0.2252(4) 0.0158(4) 0.2216(3) 0.0198(6) Uani 1 1 d . . . C2 C 0.2562(4) 0.1531(4) 0.1906(3) 0.0188(6) Uani 1 1 d . . . C3 C 0.0728(4) -0.1223(4) 0.1366(3) 0.0188(6) Uani 1 1 d . . . C4 C 0.3425(4) 0.0085(4) 0.3343(3) 0.0215(6) Uani 1 1 d . . . C5 C 0.3168(5) 0.7540(4) -0.1006(4) 0.0280(7) Uani 1 1 d . . . H5A H 0.2065 0.7814 -0.0973 0.042 Uiso 1 1 calc R . . H5B H 0.3016 0.6698 -0.1938 0.042 Uiso 1 1 calc R . . H5C H 0.4128 0.8577 -0.0749 0.042 Uiso 1 1 calc R . . C6 C 0.3623(4) 0.6821(4) -0.0022(3) 0.0205(6) Uani 1 1 d . . . C7 C 0.5191(4) 0.7629(4) 0.1051(3) 0.0231(7) Uani 1 1 d . . . H7 H 0.5971 0.8620 0.1111 0.028 Uiso 1 1 calc R . . C8 C 0.5731(4) 0.7116(4) 0.2057(3) 0.0217(6) Uani 1 1 d . . . C9 C 0.7434(5) 0.8157(4) 0.3196(3) 0.0293(7) Uani 1 1 d . . . H9A H 0.8242 0.7476 0.3150 0.044 Uiso 1 1 calc R . . H9B H 0.7201 0.8507 0.4079 0.044 Uiso 1 1 calc R . . H9C H 0.7976 0.9170 0.3104 0.044 Uiso 1 1 calc R . . H1O H 0.008(5) 0.525(5) 0.160(4) 0.023(11) Uiso 1 1 d . . . H2O H 0.149(5) 0.635(5) 0.246(4) 0.023(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 Cu1 0.0203(2) 0.0183(2) 0.0200(2) 0.01288(16) 0.00209(16) 0.00428(15) O1 0.0313(12) 0.0192(11) 0.0183(11) 0.0109(9) -0.0044(10) 0.0045(9) O2 0.0215(11) 0.0211(11) 0.0245(12) 0.0156(9) 0.0042(9) 0.0058(9) O3 0.0232(11) 0.0202(11) 0.0230(11) 0.0129(9) 0.0043(9) 0.0061(9) O4 0.0238(13) 0.0211(13) 0.0224(13) 0.0118(10) 0.0009(11) 0.0066(11) O5 0.109(4) 0.163(5) 0.098(4) 0.079(4) 0.026(3) 0.018(4) O6 0.112(3) 0.0441(19) 0.052(2) 0.0266(17) -0.018(2) -0.002(2) N1 0.0326(16) 0.0218(14) 0.0227(14) 0.0141(12) -0.0096(12) 0.0000(12) N2 0.0239(14) 0.0226(14) 0.0251(15) 0.0144(12) -0.0011(12) 0.0031(11) N3 0.0241(14) 0.0222(13) 0.0252(14) 0.0171(12) 0.0028(12) 0.0056(11) C1 0.0256(16) 0.0171(14) 0.0179(15) 0.0117(12) 0.0029(13) 0.0054(12) C2 0.0174(14) 0.0226(15) 0.0141(14) 0.0088(12) -0.0012(12) 0.0067(12) C3 0.0238(16) 0.0222(15) 0.0181(15) 0.0151(13) 0.0053(13) 0.0114(13) C4 0.0288(17) 0.0174(14) 0.0147(15) 0.0068(12) 0.0022(13) 0.0059(12) C5 0.0288(18) 0.0269(17) 0.0307(18) 0.0200(15) 0.0049(15) 0.0037(14) C6 0.0254(16) 0.0185(14) 0.0220(16) 0.0104(12) 0.0106(13) 0.0098(12) C7 0.0260(16) 0.0182(15) 0.0255(17) 0.0118(13) 0.0078(14) 0.0042(13) C8 0.0238(16) 0.0210(15) 0.0204(16) 0.0082(12) 0.0080(13) 0.0086(12) C9 0.0283(17) 0.0300(18) 0.0228(17) 0.0101(14) 0.0040(14) 0.0035(14) _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 1.917(2) . ? Cu1 O2 1.931(2) . ? Cu1 N3 1.977(3) 2 ? Cu1 N2 1.984(3) . ? Cu1 O4 2.283(2) . ? O1 C4 1.251(4) . ? O2 C6 1.279(3) . ? O3 C8 1.279(4) . ? O3 O6 2.892(4) . ? O4 H1O 0.77(4) . ? O4 H2O 0.71(4) . ? O5 O6 2.649(7) . ? O5 O5 2.655(12) 2_766 ? O5 O4 2.917(5) 2_666 ? N1 C4 1.327(4) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 C2 1.144(4) . ? N3 C3 1.145(4) . ? N3 Cu1 1.977(3) 2 ? C1 C3 1.395(4) . ? C1 C2 1.397(4) . ? C1 C4 1.451(4) . ? C5 C6 1.501(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.382(5) . ? C7 C8 1.399(4) . ? C7 H7 0.9500 . ? C8 C9 1.494(5) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? 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 O2 93.81(9) . . ? O3 Cu1 N3 171.07(10) . 2 ? O2 Cu1 N3 88.25(10) . 2 ? O3 Cu1 N2 90.35(10) . . ? O2 Cu1 N2 170.56(10) . . ? N3 Cu1 N2 86.38(11) 2 . ? O3 Cu1 O4 94.53(10) . . ? O2 Cu1 O4 94.89(9) . . ? N3 Cu1 O4 93.95(11) 2 . ? N2 Cu1 O4 93.21(10) . . ? C6 O2 Cu1 125.3(2) . . ? C8 O3 Cu1 125.8(2) . . ? C8 O3 O6 123.0(2) . . ? Cu1 O3 O6 111.09(11) . . ? Cu1 O4 H1O 106(3) . . ? Cu1 O4 H2O 105(3) . . ? H1O O4 H2O 114(4) . . ? O6 O5 O5 98.3(3) . 2_766 ? O6 O5 O4 105.91(18) . 2_666 ? O5 O5 O4 111.8(3) 2_766 2_666 ? O5 O6 O3 126.80(18) . . ? C4 N1 H1A 120.0 . . ? C4 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C2 N2 Cu1 166.4(3) . . ? C3 N3 Cu1 171.3(2) . 2 ? C3 C1 C2 117.1(3) . . ? C3 C1 C4 119.0(2) . . ? C2 C1 C4 123.9(3) . . ? N2 C2 C1 178.2(3) . . ? N3 C3 C1 178.9(3) . . ? O1 C4 N1 121.8(3) . . ? O1 C4 C1 119.8(3) . . ? N1 C4 C1 118.4(3) . . ? C6 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C6 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O2 C6 C7 125.0(3) . . ? O2 C6 C5 114.6(3) . . ? C7 C6 C5 120.4(3) . . ? C6 C7 C8 125.6(3) . . ? C6 C7 H7 117.2 . . ? C8 C7 H7 117.2 . . ? O3 C8 C7 124.4(3) . . ? O3 C8 C9 115.7(3) . . ? C7 C8 C9 119.9(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 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 H1A O1 0.88 2.01 2.883(3) 171.3 2_656 N1 H1B O6 0.88 2.14 2.985(4) 161.3 . O4 H1O O2 0.77(4) 2.09(4) 2.860(4) 176(4) 2_565 O4 H2O O1 0.71(4) 2.03(4) 2.738(3) 175(4) 1_565 _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.745 _refine_diff_density_min -0.610 _refine_diff_density_rms 0.095 data_4 _database_code_depnum_ccdc_archive 'CCDC 698654' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [Cu(cdm)2(NH2(CH2)3NH2)2] ; _chemical_name_common '[Cu(cdm)2(NH2(CH2)3NH2)2]' _chemical_melting_point ? _chemical_formula_moiety 'C14 H24 Cu1 N10 O2' _chemical_formula_sum 'C14 H24 Cu1 N10 O2' _chemical_formula_weight 427.97 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+1/4, -y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+1/4, -y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+3/4, -y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' _cell_length_a 17.8128(12) _cell_length_b 28.8740(30) _cell_length_c 7.1606(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3682.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 5531 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1784 _exptl_absorpt_coefficient_mu 1.220 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7583 _exptl_absorpt_correction_T_max 0.9760 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _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 'Bruker X8 Apex II CCD' _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_% ? _diffrn_reflns_number 5531 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2092 _reflns_number_gt 1866 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker)' _computing_cell_refinement 'Bruker SMART (Bruker)' _computing_data_reduction 'Bruker SAINT (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.2000P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_extinction_expression ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.000(15) _refine_ls_number_reflns 2092 _refine_ls_number_parameters 123 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0650 _refine_ls_wR_factor_gt 0.0628 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0.027 _refine_ls_shift/su_mean 0.001 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 0.5000 0.45904(6) 0.01350(11) Uani 1 2 d S . . O1 O 0.40685(7) 0.49813(7) 0.4554(5) 0.0161(3) Uani 1 1 d . . . N1 N 0.31100(11) 0.45058(8) 0.5288(3) 0.0183(5) Uani 1 1 d . . . C1 C 0.28493(13) 0.52981(8) 0.4519(5) 0.0153(5) Uani 1 1 d . . . N2 N 0.14349(12) 0.51529(7) 0.4821(4) 0.0216(5) Uani 1 1 d . . . C2 C 0.20648(14) 0.52250(8) 0.4701(4) 0.0161(5) Uani 1 1 d . . . N3 N 0.33290(13) 0.61013(8) 0.3581(3) 0.0228(5) Uani 1 1 d . . . C3 C 0.31126(14) 0.57381(10) 0.4000(4) 0.0168(6) Uani 1 1 d . . . H3N H 0.0488 0.4500 0.7210 0.050 Uiso 1 1 d . . . H4N H -0.0329 0.4611 0.7661 0.050 Uiso 1 1 d . . . H6N H 0.0332 0.4652 0.1613 0.050 Uiso 1 1 d . . . H1N H 0.2665 0.4497 0.5564 0.050 Uiso 1 1 d . . . H5N H -0.0312 0.4373 0.2161 0.050 Uiso 1 1 d . . . H2N H 0.3406 0.4270 0.5471 0.050 Uiso 1 1 d . . . N4 N 0.00410(11) 0.45138(9) 0.6625(4) 0.0116(6) Uani 1 1 d . . . C4 C 0.33781(13) 0.49256(8) 0.4793(5) 0.0139(6) Uani 1 1 d . . . N5 N 0.01475(13) 0.45116(8) 0.2601(3) 0.0133(6) Uani 1 1 d . . . C5 C -0.01265(14) 0.40420(9) 0.5983(4) 0.0157(5) Uani 1 1 d . . . H5A H -0.0607 0.4044 0.5289 0.019 Uiso 1 1 calc R . . H5B H -0.0188 0.3837 0.7081 0.019 Uiso 1 1 calc R . . C6 C 0.04850(14) 0.38481(8) 0.4733(4) 0.0180(5) Uani 1 1 d . . . H6A H 0.0314 0.3546 0.4238 0.022 Uiso 1 1 calc R . . H6B H 0.0936 0.3790 0.5505 0.022 Uiso 1 1 calc R . . C7 C 0.07105(14) 0.41556(9) 0.3086(4) 0.0177(6) Uani 1 1 d . . . H7A H 0.1191 0.4311 0.3388 0.021 Uiso 1 1 calc R . . H7B H 0.0797 0.3957 0.1980 0.021 Uiso 1 1 calc R . . 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 0.0198(2) 0.01218(18) 0.00852(18) 0.000 0.000 0.0008(2) O1 0.0099(7) 0.0238(8) 0.0146(7) -0.0029(7) 0.0031(14) 0.0015(9) N1 0.0167(11) 0.0163(11) 0.0221(13) -0.0019(9) 0.0009(10) 0.0013(10) C1 0.0120(12) 0.0180(12) 0.0159(12) -0.0019(13) 0.0006(12) 0.0027(10) N2 0.0143(10) 0.0245(11) 0.0260(15) 0.0016(12) 0.0021(11) 0.0018(8) C2 0.0194(13) 0.0172(12) 0.0118(13) -0.0017(13) 0.0011(12) 0.0040(10) N3 0.0190(12) 0.0221(12) 0.0271(14) 0.0035(10) 0.0038(10) 0.0006(10) C3 0.0102(13) 0.0255(15) 0.0147(14) -0.0023(11) 0.0005(10) 0.0045(11) N4 0.0131(11) 0.0142(13) 0.0075(14) -0.0016(10) -0.0001(8) -0.0008(8) C4 0.0155(11) 0.0212(14) 0.0049(15) -0.0064(13) 0.0008(11) 0.0016(10) N5 0.0151(10) 0.0142(13) 0.0106(15) -0.0010(10) -0.0008(9) 0.0023(9) C5 0.0168(13) 0.0146(13) 0.0158(14) 0.0022(10) 0.0009(11) -0.0020(10) C6 0.0231(13) 0.0157(12) 0.0154(14) -0.0010(12) -0.0030(12) 0.0044(10) C7 0.0160(13) 0.0172(13) 0.0199(14) 0.0026(11) -0.0008(11) 0.0035(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 N5 2.021(3) 2_565 ? Cu1 N5 2.021(3) . ? Cu1 N4 2.025(3) 2_565 ? Cu1 N4 2.025(3) . ? Cu1 N2 2.599(2) . ? Cu1 N2 2.599(2) 2_565 ? O1 C4 1.252(3) . ? N1 C4 1.350(3) . ? N1 H1N 0.8173 . ? N1 H2N 0.8712 . ? C1 C3 1.404(4) . ? C1 C2 1.419(4) . ? C1 C4 1.443(3) . ? N2 C2 1.145(3) . ? N3 C3 1.157(3) . ? N4 C5 1.469(3) . ? N4 H3N 0.9005 . ? N4 H4N 1.0310 . ? N5 C7 1.477(3) . ? N5 H6N 0.8794 . ? N5 H5N 0.9641 . ? C5 C6 1.517(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.530(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? 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 N5 Cu1 N5 90.41(14) 2_565 . ? N5 Cu1 N4 91.07(7) 2_565 2_565 ? N5 Cu1 N4 174.54(9) . 2_565 ? N5 Cu1 N4 174.54(9) 2_565 . ? N5 Cu1 N4 91.07(7) . . ? N4 Cu1 N4 87.94(14) 2_565 . ? N5 Cu1 N2 93.10(9) 2_565 . ? N5 Cu1 N2 92.03(8) . . ? N4 Cu1 N2 82.64(8) 2_565 . ? N4 Cu1 N2 92.09(8) . . ? N5 Cu1 N2 92.03(8) 2_565 2_565 ? N5 Cu1 N2 93.10(9) . 2_565 ? N4 Cu1 N2 92.09(8) 2_565 2_565 ? N4 Cu1 N2 82.64(8) . 2_565 ? N2 Cu1 N2 172.71(13) . 2_565 ? C4 N1 H1N 115.8 . . ? C4 N1 H2N 121.8 . . ? H1N N1 H2N 121.7 . . ? C3 C1 C2 119.2(2) . . ? C3 C1 C4 119.5(2) . . ? C2 C1 C4 121.3(2) . . ? C2 N2 Cu1 172.0(3) . . ? N2 C2 C1 177.9(3) . . ? N3 C3 C1 179.7(3) . . ? C5 N4 Cu1 114.23(19) . . ? C5 N4 H3N 106.5 . . ? Cu1 N4 H3N 113.4 . . ? C5 N4 H4N 110.4 . . ? Cu1 N4 H4N 107.8 . . ? H3N N4 H4N 104.1 . . ? O1 C4 N1 119.9(2) . . ? O1 C4 C1 121.8(2) . . ? N1 C4 C1 118.3(2) . . ? C7 N5 Cu1 114.10(18) . . ? C7 N5 H6N 104.8 . . ? Cu1 N5 H6N 107.1 . . ? C7 N5 H5N 111.4 . . ? Cu1 N5 H5N 114.2 . . ? H6N N5 H5N 104.2 . . ? N4 C5 C6 112.4(2) . . ? N4 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? N4 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? C5 C6 C7 115.4(2) . . ? C5 C6 H6A 108.4 . . ? C7 C6 H6A 108.4 . . ? C5 C6 H6B 108.4 . . ? C7 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? N5 C7 C6 114.0(2) . . ? N5 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? N5 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? 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 N4 H3N O1 0.90 2.38 3.007(4) 126.3 10_565 N4 H4N O1 1.03 2.03 3.037(4) 163.8 9_455 N5 H6N O1 0.88 2.11 2.976(4) 170.0 10_564 N5 H5N N3 0.96 2.53 3.335(3) 140.7 7_544 N1 H2N N3 0.87 2.40 3.274(3) 176.9 15_545 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.374 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.061 data_5 _database_code_depnum_ccdc_archive 'CCDC 698655' _audit_creation_method SHELXL-97 _chemical_name_systematic ; MnPhenCl ; _chemical_name_common MnPhenCl _chemical_melting_point ? _chemical_formula_moiety 'C28 H19 Cl1 Mn1 N7 O1.50, C1 O1 H4' _chemical_formula_sum 'C29 H23 Cl1 Mn1 N7 O2.50' _chemical_formula_weight 599.93 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5476(7) _cell_length_b 11.5860(7) _cell_length_c 12.2153(7) _cell_angle_alpha 88.998(3) _cell_angle_beta 67.186(2) _cell_angle_gamma 84.951(3) _cell_volume 1370.42(15) _cell_formula_units_Z 2 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 21186 _cell_measurement_theta_min 2.10 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 614 _exptl_absorpt_coefficient_mu 0.622 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8353 _exptl_absorpt_correction_T_max 0.8856 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _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 'Bruker X8 Apex II CCD' _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_% ? _diffrn_reflns_number 21186 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6270 _reflns_number_gt 5152 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker)' _computing_cell_refinement 'Bruker SMART (Bruker)' _computing_data_reduction 'Bruker SAINT (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.2000P)^2^+0.0000P] 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_extinction_expression ? _refine_ls_number_reflns 6270 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1089 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 Mn1 Mn 0.36462(3) 0.19778(2) 0.26708(3) 0.01762(10) Uani 1 1 d . . . Cl1 Cl 0.38510(5) -0.00110(4) 0.18791(5) 0.02302(13) Uani 1 1 d . . . O1 O 0.57829(15) 0.21548(12) 0.19990(13) 0.0238(3) Uani 1 1 d . . . N5 N 0.35142(19) 0.39488(15) 0.30797(16) 0.0220(4) Uani 1 1 d . . . C4 C 0.6946(2) 0.16477(17) 0.13984(18) 0.0190(4) Uani 1 1 d . . . N4 N 0.32251(18) 0.29251(14) 0.12127(15) 0.0205(4) Uani 1 1 d . . . N1 N 0.7088(2) 0.07879(16) 0.06314(17) 0.0238(4) Uani 1 1 d . . . C2 C 0.9486(2) 0.15290(17) 0.08914(18) 0.0208(4) Uani 1 1 d . . . C16 C 0.3255(2) 0.40990(18) 0.12118(19) 0.0217(4) Uani 1 1 d . . . C1 C 0.8140(2) 0.20330(17) 0.15244(18) 0.0197(4) Uani 1 1 d . . . C15 C 0.3436(2) 0.46367(18) 0.21883(19) 0.0223(4) Uani 1 1 d . . . C3 C 0.7929(2) 0.29895(18) 0.22844(19) 0.0231(4) Uani 1 1 d . . . C14 C 0.3695(3) 0.4445(2) 0.3967(2) 0.0294(5) Uani 1 1 d . . . H14 H 0.3735 0.3973 0.4598 0.035 Uiso 1 1 calc R . . C8 C 0.3144(3) 0.4785(2) 0.0289(2) 0.0290(5) Uani 1 1 d . . . C10 C 0.3428(3) 0.6512(2) 0.1225(2) 0.0368(6) Uani 1 1 d . . . H10 H 0.3494 0.7325 0.1224 0.044 Uiso 1 1 calc R . . C5 C 0.3079(2) 0.2429(2) 0.0303(2) 0.0275(5) Uani 1 1 d . . . H5 H 0.3085 0.1609 0.0285 0.033 Uiso 1 1 calc R . . C11 C 0.3534(2) 0.58407(19) 0.2182(2) 0.0287(5) Uani 1 1 d . . . C12 C 0.3760(3) 0.6322(2) 0.3135(2) 0.0370(6) Uani 1 1 d . . . H12 H 0.3864 0.7126 0.3155 0.044 Uiso 1 1 calc R . . C9 C 0.3238(3) 0.6009(2) 0.0326(2) 0.0384(6) Uani 1 1 d . . . H9 H 0.3163 0.6474 -0.0298 0.046 Uiso 1 1 calc R . . C13 C 0.3830(3) 0.5631(2) 0.4026(2) 0.0388(6) Uani 1 1 d . . . H13 H 0.3968 0.5949 0.4679 0.047 Uiso 1 1 calc R . . N6 N 0.37304(18) 0.16318(14) 0.44731(15) 0.0203(4) Uani 1 1 d . . . N7 N 0.14381(18) 0.18253(15) 0.39633(15) 0.0208(4) Uani 1 1 d . . . C7 C 0.2961(3) 0.4227(2) -0.0644(2) 0.0355(6) Uani 1 1 d . . . H7 H 0.2871 0.4663 -0.1279 0.043 Uiso 1 1 calc R . . C6 C 0.2915(3) 0.3054(2) -0.0630(2) 0.0355(6) Uani 1 1 d . . . H6 H 0.2773 0.2667 -0.1246 0.043 Uiso 1 1 calc R . . C28 C 0.2515(2) 0.14001(16) 0.53468(18) 0.0193(4) Uani 1 1 d . . . C27 C 0.1299(2) 0.15017(17) 0.50797(18) 0.0203(4) Uani 1 1 d . . . C18 C 0.4841(3) 0.12364(18) 0.5833(2) 0.0267(5) Uani 1 1 d . . . H18 H 0.5671 0.1186 0.5971 0.032 Uiso 1 1 calc R . . C17 C 0.4851(2) 0.15627(18) 0.4722(2) 0.0243(5) Uani 1 1 d . . . H17 H 0.5698 0.1743 0.4119 0.029 Uiso 1 1 calc R . . C20 C 0.2413(2) 0.10736(17) 0.64940(19) 0.0237(5) Uani 1 1 d . . . C19 C 0.3627(3) 0.09908(18) 0.6716(2) 0.0271(5) Uani 1 1 d . . . H19 H 0.3606 0.0766 0.7474 0.033 Uiso 1 1 calc R . . C26 C 0.0320(2) 0.1926(2) 0.3720(2) 0.0271(5) Uani 1 1 d . . . H26 H 0.0406 0.2166 0.2949 0.032 Uiso 1 1 calc R . . C21 C 0.1092(3) 0.0846(2) 0.7372(2) 0.0305(5) Uani 1 1 d . . . H21 H 0.1019 0.0632 0.8147 0.037 Uiso 1 1 calc R . . C22 C -0.0043(3) 0.0930(2) 0.7120(2) 0.0319(5) Uani 1 1 d . . . H22 H -0.0903 0.0766 0.7716 0.038 Uiso 1 1 calc R . . C23 C 0.0025(2) 0.12643(18) 0.5960(2) 0.0259(5) Uani 1 1 d . . . C24 C -0.1126(2) 0.1365(2) 0.5655(2) 0.0324(5) Uani 1 1 d . . . H24 H -0.2004 0.1202 0.6221 0.039 Uiso 1 1 calc R . . C25 C -0.0984(2) 0.1699(2) 0.4541(2) 0.0329(5) Uani 1 1 d . . . H25 H -0.1761 0.1777 0.4325 0.040 Uiso 1 1 calc R . . N2 N 1.05751(19) 0.10881(16) 0.03792(17) 0.0279(4) Uani 1 1 d . . . N3 N 0.7737(2) 0.37725(18) 0.29152(18) 0.0349(5) Uani 1 1 d . . . O2 O 0.8264(3) 0.61202(19) 0.3001(3) 0.0820(9) Uani 1 1 d . . . H2 H 0.7951 0.5469 0.3074 0.098 Uiso 1 1 calc R . . H2N H 0.787(3) 0.040(2) 0.026(2) 0.031(7) Uiso 1 1 d . . . H1N H 0.637(3) 0.055(2) 0.062(2) 0.034(7) Uiso 1 1 d . . . O3 O -0.0151(9) 0.4667(11) 0.5523(7) 0.171(5) Uani 0.50 1 d P A -1 C29 C 0.9590(5) 0.6062(4) 0.2081(5) 0.0971(16) Uani 1 1 d . . . H29A H 0.9692 0.6774 0.1621 0.146 Uiso 1 1 calc R . . H29B H 0.9706 0.5394 0.1559 0.146 Uiso 1 1 calc R . . H29C H 1.0292 0.5978 0.2425 0.146 Uiso 1 1 calc R . . 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 Mn1 0.01569(17) 0.01940(16) 0.01695(17) 0.00270(12) -0.00536(13) -0.00237(12) Cl1 0.0223(3) 0.0213(2) 0.0239(3) 0.00053(19) -0.0066(2) -0.0053(2) O1 0.0158(8) 0.0227(7) 0.0294(8) -0.0004(6) -0.0050(7) -0.0015(6) N5 0.0199(9) 0.0214(8) 0.0220(9) -0.0022(7) -0.0054(8) 0.0009(7) C4 0.0180(10) 0.0203(9) 0.0182(10) 0.0055(8) -0.0063(8) -0.0024(8) N4 0.0192(9) 0.0210(8) 0.0210(9) 0.0021(7) -0.0071(8) -0.0040(7) N1 0.0147(9) 0.0288(10) 0.0268(10) -0.0046(8) -0.0064(8) -0.0029(8) C2 0.0209(11) 0.0227(10) 0.0214(10) 0.0007(8) -0.0101(9) -0.0072(8) C16 0.0198(11) 0.0226(10) 0.0217(11) 0.0042(8) -0.0068(9) -0.0027(8) C1 0.0182(10) 0.0211(10) 0.0195(10) 0.0012(8) -0.0067(9) -0.0027(8) C15 0.0186(11) 0.0211(10) 0.0226(11) 0.0005(8) -0.0037(9) 0.0002(8) C3 0.0212(11) 0.0273(11) 0.0217(11) 0.0042(9) -0.0088(9) -0.0047(9) C14 0.0342(13) 0.0280(11) 0.0242(12) -0.0052(9) -0.0103(10) 0.0023(10) C8 0.0318(13) 0.0286(11) 0.0263(12) 0.0071(9) -0.0105(10) -0.0049(10) C10 0.0399(15) 0.0200(11) 0.0445(15) 0.0063(10) -0.0104(13) -0.0014(10) C5 0.0303(13) 0.0293(11) 0.0264(12) 0.0022(9) -0.0138(10) -0.0070(10) C11 0.0286(13) 0.0212(10) 0.0300(12) -0.0004(9) -0.0047(10) -0.0011(9) C12 0.0420(15) 0.0210(11) 0.0417(15) -0.0084(10) -0.0092(12) -0.0015(10) C9 0.0469(16) 0.0280(12) 0.0398(15) 0.0136(11) -0.0167(13) -0.0037(11) C13 0.0488(17) 0.0333(13) 0.0328(14) -0.0143(11) -0.0145(13) 0.0002(12) N6 0.0212(9) 0.0196(8) 0.0207(9) 0.0025(7) -0.0087(8) -0.0020(7) N7 0.0186(9) 0.0232(9) 0.0186(9) 0.0037(7) -0.0056(7) -0.0007(7) C7 0.0430(15) 0.0410(14) 0.0273(13) 0.0136(11) -0.0191(12) -0.0048(12) C6 0.0442(16) 0.0418(14) 0.0274(13) 0.0034(10) -0.0205(12) -0.0083(12) C28 0.0225(11) 0.0150(9) 0.0189(10) 0.0004(8) -0.0067(9) 0.0004(8) C27 0.0192(11) 0.0202(9) 0.0189(10) 0.0028(8) -0.0051(9) -0.0006(8) C18 0.0345(13) 0.0222(10) 0.0326(12) 0.0000(9) -0.0231(11) -0.0022(9) C17 0.0266(12) 0.0214(10) 0.0288(12) 0.0012(9) -0.0146(10) -0.0041(9) C20 0.0321(12) 0.0190(10) 0.0188(10) 0.0011(8) -0.0088(10) -0.0008(9) C19 0.0429(14) 0.0205(10) 0.0238(11) 0.0003(9) -0.0198(11) -0.0006(9) C26 0.0199(11) 0.0344(12) 0.0258(12) 0.0067(9) -0.0082(10) -0.0012(9) C21 0.0403(15) 0.0300(12) 0.0168(11) 0.0051(9) -0.0070(10) -0.0003(10) C22 0.0302(13) 0.0344(12) 0.0201(11) 0.0074(9) 0.0016(10) -0.0012(10) C23 0.0236(12) 0.0239(10) 0.0232(11) 0.0046(9) -0.0021(9) -0.0002(9) C24 0.0180(11) 0.0372(13) 0.0323(13) 0.0074(10) 0.0005(10) -0.0019(10) C25 0.0170(11) 0.0443(14) 0.0368(14) 0.0101(11) -0.0099(10) -0.0033(10) N2 0.0189(10) 0.0325(10) 0.0327(11) -0.0059(8) -0.0100(9) -0.0026(8) N3 0.0378(12) 0.0346(11) 0.0323(11) -0.0067(9) -0.0133(10) -0.0023(9) O2 0.095(2) 0.0398(13) 0.0863(19) -0.0218(13) -0.0048(16) -0.0182(13) O3 0.091(6) 0.296(15) 0.138(8) -0.075(10) -0.066(7) 0.036(7) C29 0.070(3) 0.061(2) 0.169(5) 0.000(3) -0.055(3) -0.013(2) _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 Mn1 O1 2.1062(15) . ? Mn1 N4 2.2436(18) . ? Mn1 N6 2.2649(17) . ? Mn1 N7 2.2715(18) . ? Mn1 N5 2.3268(17) . ? Mn1 Cl1 2.4738(6) . ? O1 C4 1.256(2) . ? N5 C14 1.320(3) . ? N5 C15 1.362(3) . ? C4 N1 1.338(3) . ? C4 C1 1.436(3) . ? N4 C5 1.326(3) . ? N4 C16 1.363(3) . ? N1 H2N 0.86(3) . ? N1 H1N 0.84(3) . ? C2 N2 1.150(3) . ? C2 C1 1.404(3) . ? C16 C8 1.405(3) . ? C16 C15 1.439(3) . ? C1 C3 1.404(3) . ? C15 C11 1.407(3) . ? C3 N3 1.153(3) . ? C14 C13 1.400(3) . ? C14 H14 0.9500 . ? C8 C7 1.403(3) . ? C8 C9 1.433(3) . ? C10 C9 1.341(4) . ? C10 C11 1.428(3) . ? C10 H10 0.9500 . ? C5 C6 1.398(3) . ? C5 H5 0.9500 . ? C11 C12 1.409(3) . ? C12 C13 1.361(4) . ? C12 H12 0.9500 . ? C9 H9 0.9500 . ? C13 H13 0.9500 . ? N6 C17 1.325(3) . ? N6 C28 1.358(3) . ? N7 C26 1.319(3) . ? N7 C27 1.363(3) . ? C7 C6 1.363(3) . ? C7 H7 0.9500 . ? C6 H6 0.9500 . ? C28 C20 1.411(3) . ? C28 C27 1.436(3) . ? C27 C23 1.404(3) . ? C18 C19 1.366(3) . ? C18 C17 1.399(3) . ? C18 H18 0.9500 . ? C17 H17 0.9500 . ? C20 C19 1.404(3) . ? C20 C21 1.434(3) . ? C19 H19 0.9500 . ? C26 C25 1.397(3) . ? C26 H26 0.9500 . ? C21 C22 1.342(4) . ? C21 H21 0.9500 . ? C22 C23 1.438(3) . ? C22 H22 0.9500 . ? C23 C24 1.398(3) . ? C24 C25 1.363(3) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? O2 C29 1.411(5) . ? O2 H2 0.8400 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 N4 96.59(6) . . ? O1 Mn1 N6 88.29(6) . . ? N4 Mn1 N6 159.58(6) . . ? O1 Mn1 N7 161.21(6) . . ? N4 Mn1 N7 99.23(6) . . ? N6 Mn1 N7 73.41(6) . . ? O1 Mn1 N5 82.44(6) . . ? N4 Mn1 N5 73.02(6) . . ? N6 Mn1 N5 88.07(6) . . ? N7 Mn1 N5 92.51(6) . . ? O1 Mn1 Cl1 95.83(4) . . ? N4 Mn1 Cl1 97.46(5) . . ? N6 Mn1 Cl1 101.77(4) . . ? N7 Mn1 Cl1 92.13(5) . . ? N5 Mn1 Cl1 169.98(5) . . ? C4 O1 Mn1 143.46(13) . . ? C14 N5 C15 117.83(18) . . ? C14 N5 Mn1 127.87(15) . . ? C15 N5 Mn1 113.58(13) . . ? O1 C4 N1 121.37(19) . . ? O1 C4 C1 118.49(18) . . ? N1 C4 C1 120.11(19) . . ? C5 N4 C16 117.88(18) . . ? C5 N4 Mn1 125.28(15) . . ? C16 N4 Mn1 116.54(13) . . ? C4 N1 H2N 121.8(17) . . ? C4 N1 H1N 117.9(18) . . ? H2N N1 H1N 119(2) . . ? N2 C2 C1 178.2(2) . . ? N4 C16 C8 122.43(19) . . ? N4 C16 C15 117.95(18) . . ? C8 C16 C15 119.61(19) . . ? C3 C1 C2 119.72(18) . . ? C3 C1 C4 117.22(18) . . ? C2 C1 C4 123.01(18) . . ? N5 C15 C11 122.8(2) . . ? N5 C15 C16 118.09(18) . . ? C11 C15 C16 119.1(2) . . ? N3 C3 C1 179.0(3) . . ? N5 C14 C13 123.4(2) . . ? N5 C14 H14 118.3 . . ? C13 C14 H14 118.3 . . ? C7 C8 C16 117.8(2) . . ? C7 C8 C9 123.0(2) . . ? C16 C8 C9 119.2(2) . . ? C9 C10 C11 120.7(2) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? N4 C5 C6 123.2(2) . . ? N4 C5 H5 118.4 . . ? C6 C5 H5 118.4 . . ? C15 C11 C12 117.1(2) . . ? C15 C11 C10 119.9(2) . . ? C12 C11 C10 123.0(2) . . ? C13 C12 C11 119.8(2) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C10 C9 C8 121.4(2) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C12 C13 C14 119.0(2) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C17 N6 C28 118.29(18) . . ? C17 N6 Mn1 126.33(15) . . ? C28 N6 Mn1 115.23(13) . . ? C26 N7 C27 117.86(19) . . ? C26 N7 Mn1 127.00(15) . . ? C27 N7 Mn1 114.91(14) . . ? C6 C7 C8 119.5(2) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C7 C6 C5 119.2(2) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? N6 C28 C20 122.4(2) . . ? N6 C28 C27 118.04(18) . . ? C20 C28 C27 119.60(19) . . ? N7 C27 C23 122.6(2) . . ? N7 C27 C28 117.86(19) . . ? C23 C27 C28 119.58(19) . . ? C19 C18 C17 119.3(2) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? N6 C17 C18 123.0(2) . . ? N6 C17 H17 118.5 . . ? C18 C17 H17 118.5 . . ? C19 C20 C28 117.6(2) . . ? C19 C20 C21 123.2(2) . . ? C28 C20 C21 119.2(2) . . ? C18 C19 C20 119.5(2) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? N7 C26 C25 123.3(2) . . ? N7 C26 H26 118.4 . . ? C25 C26 H26 118.4 . . ? C22 C21 C20 121.3(2) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C23 120.9(2) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C24 C23 C27 117.5(2) . . ? C24 C23 C22 123.1(2) . . ? C27 C23 C22 119.4(2) . . ? C25 C24 C23 119.8(2) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C26 119.0(2) . . ? C24 C25 H25 120.5 . . ? C26 C25 H25 120.5 . . ? C29 O2 H2 109.5 . . ? O2 C29 H29A 109.5 . . ? O2 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O2 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 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 O2 H2 N3 0.84 2.02 2.835(3) 163.9 . N1 H2N N2 0.86(3) 2.20(3) 3.019(3) 159(2) 2_755 N1 H1N Cl1 0.84(3) 2.64(3) 3.363(2) 146(2) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.687 _refine_diff_density_min -0.561 _refine_diff_density_rms 0.069