Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Hans-Conrad zur Loye' _publ_contact_author_address ; Department of Chemistry and Biochemistry University of South Carolina 631 Sumter Street Columbia SC 29208 U S A ; _publ_contact_author_email ZURLOYE@MAIL.CHEM.SC.EDU _publ_section_title ; A New 2-carboxylate-substituted 4,4'-bipyridine Ligand: Coordination Chemistry of 4,4'-bipyridine-2-carboxylic Acid and its Synthetic Intermediate 2-methyl-4,4'-bipyridine ; loop_ _publ_author_name 'Hans-Conrad Zur Loye' 'Chun-Long Chen.' 'Joseph M. Ellsworth' 'Andrea M. Gosforth' ; M.D.Smith ; 'Cheng-Yong Su.' data_mp _database_code_depnum_ccdc_archive 'CCDC 267236' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 Mn N4 O8' _chemical_formula_sum 'C11 H14 Mn N4 O8' _chemical_formula_weight 385.20 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' Mn Mn 0.3368 0.7283 '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/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 24.007(3) _cell_length_b 7.2451(9) _cell_length_c 19.331(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.671(2) _cell_angle_gamma 90.00 _cell_volume 3079.5(7) _cell_formula_units_Z 8 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 7482 _cell_measurement_theta_min 2.300 _cell_measurement_theta_max 25.122 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 0.908 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 29733 _diffrn_reflns_av_R_equivalents 0.0833 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 0.93 _diffrn_reflns_theta_max 25.15 _reflns_number_total 5505 _reflns_number_gt 5182 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART NT V5.625 (Bruker, 2000)' _computing_cell_refinement 'SAINT+ NT V6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT+ NT V6.22' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V6.1 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V6.1' _refine_special_details ; Crystal twinned by pseudo-merohedry True primitive monoclinic cell metrically consistent with C-centered orthorhombic cell of twice the volume. Crystal twinned to emulate the C-centered cell. Twin law applied: TWIN 1 0 1 0 -1 0 0 0 -1 BASF 0.44705 Twin fraction = BASF value. 28 "same-distance" (SHELX SADI) restraints used for the aqua O-H bonds. Water hydrogens refined with common Ueq. 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^)+(0.0452P)^2^+0.1310P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5505 _refine_ls_number_parameters 461 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0958 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.122 _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 Mn1 Mn 0.29557(3) 0.18741(8) 0.45043(4) 0.02316(16) Uani 1 1 d . . . Mn2 Mn 0.20669(3) 0.71043(8) 0.64524(4) 0.02550(17) Uani 1 1 d . . . C1 C 0.36374(17) 0.0892(6) 0.6230(2) 0.0249(9) Uani 1 1 d . . . H1 H 0.3247 0.0441 0.6160 0.030 Uiso 1 1 calc R . . C2 C 0.40907(16) 0.0859(5) 0.6944(2) 0.0221(9) Uani 1 1 d . . . H2 H 0.4012 0.0429 0.7360 0.026 Uiso 1 1 calc R . . C3 C 0.46690(16) 0.1469(5) 0.7047(2) 0.0239(9) Uani 1 1 d . . . C4 C 0.47674(17) 0.2051(5) 0.6422(2) 0.0237(9) Uani 1 1 d . . . H4 H 0.5162 0.2417 0.6472 0.028 Uiso 1 1 calc R . . C5 C 0.42854(18) 0.2088(6) 0.5731(3) 0.0293(10) Uani 1 1 d . . . H5 H 0.4353 0.2524 0.5307 0.035 Uiso 1 1 calc R . . C6 C 0.62037(18) 0.0917(6) 0.8636(3) 0.0299(10) Uani 1 1 d . . . H6 H 0.6601 0.0534 0.8705 0.036 Uiso 1 1 calc R . . C7 C 0.57582(16) 0.0979(6) 0.7911(2) 0.0256(9) Uani 1 1 d . . . H7 H 0.5850 0.0687 0.7489 0.031 Uiso 1 1 calc R . . C8 C 0.51713(17) 0.1482(5) 0.7815(2) 0.0226(9) Uani 1 1 d . . . C9 C 0.50662(18) 0.1959(5) 0.8442(2) 0.0254(9) Uani 1 1 d . . . H9 H 0.4671 0.2331 0.8388 0.031 Uiso 1 1 calc R . . C10 C 0.55361(19) 0.1895(5) 0.9149(3) 0.0301(10) Uani 1 1 d . . . C11 C 0.5445(2) 0.2434(8) 0.9852(3) 0.0484(13) Uani 1 1 d . . . H11A H 0.5462 0.1329 1.0151 0.073 Uiso 1 1 calc R . . H11B H 0.5047 0.3030 0.9707 0.073 Uiso 1 1 calc R . . H11C H 0.5766 0.3294 1.0152 0.073 Uiso 1 1 calc R . . C12 C 0.13781(17) 0.5724(5) 0.7456(2) 0.0274(9) Uani 1 1 d . . . H12 H 0.1769 0.5254 0.7763 0.033 Uiso 1 1 calc R . . C13 C 0.09327(16) 0.5640(5) 0.7731(2) 0.0252(9) Uani 1 1 d . . . H13 H 0.1021 0.5157 0.8221 0.030 Uiso 1 1 calc R . . C14 C 0.03489(17) 0.6271(5) 0.7283(2) 0.0243(9) Uani 1 1 d . . . C15 C 0.02480(18) 0.6930(6) 0.6565(2) 0.0289(10) Uani 1 1 d . . . H15 H -0.0147 0.7310 0.6230 0.035 Uiso 1 1 calc R . . C16 C 0.07293(17) 0.7024(6) 0.6347(2) 0.0280(10) Uani 1 1 d . . . H16 H 0.0657 0.7535 0.5866 0.034 Uiso 1 1 calc R . . C17 C -0.11722(17) 0.5772(5) 0.7413(3) 0.0276(9) Uani 1 1 d . . . H17 H -0.1574 0.5393 0.7100 0.033 Uiso 1 1 calc R . . C18 C -0.07410(16) 0.5788(5) 0.7105(2) 0.0266(9) Uani 1 1 d . . . H18 H -0.0849 0.5472 0.6590 0.032 Uiso 1 1 calc R . . C19 C -0.01406(16) 0.6282(5) 0.7571(2) 0.0231(9) Uani 1 1 d . . . C20 C -0.00202(19) 0.6761(5) 0.8311(3) 0.0296(10) Uani 1 1 d . . . H20 H 0.0382 0.7079 0.8645 0.036 Uiso 1 1 calc R . . C21 C -0.04898(19) 0.6777(6) 0.8568(3) 0.0315(10) Uani 1 1 d . . . C22 C -0.0380(2) 0.7345(8) 0.9350(3) 0.0445(12) Uani 1 1 d . . . H22A H -0.0713 0.8140 0.9341 0.067 Uiso 1 1 calc R . . H22B H 0.0005 0.8023 0.9571 0.067 Uiso 1 1 calc R . . H22C H -0.0359 0.6246 0.9656 0.067 Uiso 1 1 calc R . . N1 N 0.37202(15) 0.1533(5) 0.5626(2) 0.0255(8) Uani 1 1 d . . . N2 N 0.61028(14) 0.1370(5) 0.9246(2) 0.0303(8) Uani 1 1 d . . . N3 N 0.12945(14) 0.6433(5) 0.6778(2) 0.0282(8) Uani 1 1 d . . . N4 N -0.10588(15) 0.6253(5) 0.8120(2) 0.0304(8) Uani 1 1 d . . . N5 N 0.33201(16) 0.1624(5) 0.3332(2) 0.0316(9) Uani 1 1 d . . . N6 N 0.18694(15) 0.1957(5) 0.4665(2) 0.0290(8) Uani 1 1 d . . . N7 N 0.17610(16) 0.6914(5) 0.4930(2) 0.0351(9) Uani 1 1 d . . . N8 N 0.30344(15) 0.8241(5) 0.7741(2) 0.0281(8) Uani 1 1 d . . . O1 O 0.28217(15) -0.1076(5) 0.43707(19) 0.0372(8) Uani 1 1 d D . . H1A H 0.269(2) -0.165(7) 0.464(3) 0.067(6) Uiso 1 1 d D . . H1B H 0.263(2) -0.122(9) 0.3907(14) 0.067(6) Uiso 1 1 d D . . O2 O 0.31029(14) 0.4770(4) 0.44632(16) 0.0320(7) Uani 1 1 d D . . H2A H 0.332(2) 0.550(6) 0.479(3) 0.067(6) Uiso 1 1 d D . . H2B H 0.316(2) 0.512(8) 0.409(2) 0.067(6) Uiso 1 1 d D . . O3 O 0.23807(15) 0.4306(4) 0.65161(19) 0.0371(7) Uani 1 1 d D . . H3A H 0.263(2) 0.380(7) 0.690(2) 0.067(6) Uiso 1 1 d D . . H3B H 0.234(3) 0.371(7) 0.613(2) 0.067(6) Uiso 1 1 d D . . O4 O 0.18178(15) 0.9942(4) 0.6285(2) 0.0372(7) Uani 1 1 d D . . H4A H 0.154(2) 1.040(7) 0.638(3) 0.067(6) Uiso 1 1 d D . . H4B H 0.179(2) 1.037(8) 0.5871(19) 0.067(6) Uiso 1 1 d D . . O11 O 0.27754(12) 0.1914(4) 0.32570(18) 0.0328(7) Uani 1 1 d . . . O12 O 0.37163(14) 0.1486(5) 0.39893(18) 0.0396(8) Uani 1 1 d . . . O13 O 0.34455(15) 0.1501(5) 0.27763(18) 0.0416(8) Uani 1 1 d . . . O14 O 0.23597(13) 0.2192(5) 0.52457(17) 0.0365(8) Uani 1 1 d . . . O15 O 0.19079(13) 0.1951(4) 0.40424(18) 0.0367(7) Uani 1 1 d . . . O16 O 0.13840(14) 0.1740(5) 0.4734(2) 0.0513(10) Uani 1 1 d . . . O17 O 0.22837(12) 0.7501(4) 0.53816(17) 0.0324(7) Uani 1 1 d . . . O18 O 0.14075(14) 0.6398(5) 0.52274(19) 0.0434(8) Uani 1 1 d . . . O19 O 0.16269(16) 0.6891(5) 0.42504(19) 0.0516(9) Uani 1 1 d . . . O20 O 0.25789(14) 0.7585(5) 0.7831(2) 0.0428(8) Uani 1 1 d . . . O21 O 0.30322(13) 0.8147(4) 0.70926(17) 0.0334(7) Uani 1 1 d . . . O22 O 0.34656(12) 0.8943(5) 0.82677(17) 0.0379(8) Uani 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 Mn1 0.0236(3) 0.0221(3) 0.0219(3) 0.0006(3) 0.0072(3) 0.0034(2) Mn2 0.0208(3) 0.0289(4) 0.0264(3) -0.0035(3) 0.0091(3) -0.0034(3) C1 0.022(2) 0.026(2) 0.027(2) 0.0009(17) 0.0095(17) 0.0005(16) C2 0.0217(19) 0.0168(19) 0.028(2) 0.0050(16) 0.0107(17) 0.0018(15) C3 0.0215(19) 0.0149(18) 0.033(2) 0.0021(17) 0.0081(17) 0.0051(15) C4 0.023(2) 0.020(2) 0.028(2) -0.0014(18) 0.0103(18) -0.0028(16) C5 0.035(2) 0.023(2) 0.033(3) 0.0061(19) 0.017(2) 0.0087(18) C6 0.021(2) 0.027(2) 0.043(3) 0.008(2) 0.0139(19) 0.0008(17) C7 0.023(2) 0.026(2) 0.025(2) 0.0018(18) 0.0071(17) -0.0020(16) C8 0.025(2) 0.0114(18) 0.030(2) 0.0029(16) 0.0084(17) -0.0010(15) C9 0.025(2) 0.021(2) 0.032(2) 0.0015(18) 0.0141(19) -0.0009(16) C10 0.035(2) 0.020(2) 0.033(2) -0.0034(19) 0.012(2) -0.0074(18) C11 0.048(3) 0.054(3) 0.045(3) -0.004(3) 0.020(3) -0.001(3) C12 0.0196(19) 0.025(2) 0.032(2) 0.0009(18) 0.0046(17) -0.0016(16) C13 0.0224(19) 0.021(2) 0.029(2) 0.0019(17) 0.0075(17) -0.0031(16) C14 0.025(2) 0.0137(19) 0.028(2) -0.0018(17) 0.0053(17) -0.0024(15) C15 0.024(2) 0.030(2) 0.028(2) 0.001(2) 0.0057(18) -0.0017(17) C16 0.025(2) 0.026(2) 0.027(2) 0.0074(19) 0.0046(19) -0.0008(17) C17 0.0217(19) 0.019(2) 0.040(3) 0.004(2) 0.0098(19) -0.0016(15) C18 0.023(2) 0.025(2) 0.027(2) 0.0022(18) 0.0048(18) -0.0006(16) C19 0.022(2) 0.0161(18) 0.028(2) -0.0013(17) 0.0068(17) -0.0011(16) C20 0.030(2) 0.023(2) 0.032(2) 0.0027(19) 0.0084(19) -0.0009(17) C21 0.039(2) 0.025(2) 0.029(3) 0.0025(19) 0.012(2) -0.0043(19) C22 0.044(3) 0.051(3) 0.040(3) 0.005(3) 0.018(3) 0.003(2) N1 0.0234(17) 0.0258(19) 0.0268(19) 0.0014(15) 0.0095(15) 0.0043(14) N2 0.0271(19) 0.032(2) 0.028(2) 0.0061(16) 0.0080(16) -0.0059(15) N3 0.0238(17) 0.0247(19) 0.034(2) 0.0001(16) 0.0099(15) -0.0018(14) N4 0.0293(18) 0.0251(19) 0.037(2) 0.0019(17) 0.0139(17) 0.0017(15) N5 0.038(2) 0.031(2) 0.030(2) -0.0059(16) 0.0179(18) -0.0002(16) N6 0.0249(18) 0.030(2) 0.033(2) 0.0041(16) 0.0122(17) 0.0041(14) N7 0.032(2) 0.035(2) 0.030(2) -0.0058(17) 0.0037(17) -0.0059(16) N8 0.0293(19) 0.0268(18) 0.029(2) -0.0011(15) 0.0123(17) -0.0011(15) O1 0.0448(19) 0.0277(16) 0.040(2) 0.0041(15) 0.0184(16) 0.0010(14) O2 0.0400(17) 0.0247(16) 0.0267(18) -0.0005(13) 0.0087(14) -0.0021(13) O3 0.0488(19) 0.0288(17) 0.0294(18) -0.0027(14) 0.0111(16) 0.0063(14) O4 0.0451(18) 0.0351(17) 0.043(2) 0.0055(16) 0.0296(17) 0.0092(15) O11 0.0307(16) 0.0379(18) 0.0287(16) -0.0030(13) 0.0107(13) -0.0022(13) O12 0.0364(16) 0.048(2) 0.0273(18) -0.0004(15) 0.0053(15) 0.0051(14) O13 0.0519(19) 0.050(2) 0.0304(19) -0.0069(15) 0.0241(16) 0.0023(16) O14 0.0298(17) 0.049(2) 0.0228(17) -0.0030(14) 0.0027(15) 0.0089(14) O15 0.0360(16) 0.0472(19) 0.0257(17) -0.0027(14) 0.0111(14) -0.0001(13) O16 0.0332(18) 0.074(3) 0.055(2) 0.0008(19) 0.0257(17) 0.0018(16) O17 0.0247(15) 0.0398(17) 0.0271(17) -0.0074(14) 0.0045(13) -0.0032(13) O18 0.0371(18) 0.057(2) 0.036(2) 0.0017(16) 0.0148(15) -0.0130(16) O19 0.054(2) 0.074(3) 0.0233(19) -0.0081(18) 0.0116(16) -0.0154(18) O20 0.0303(17) 0.055(2) 0.043(2) 0.0059(17) 0.0137(16) -0.0131(15) O21 0.0292(15) 0.0423(17) 0.0305(17) -0.0063(13) 0.0139(13) -0.0075(13) O22 0.0296(16) 0.047(2) 0.0288(17) -0.0091(15) 0.0031(14) -0.0135(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 Mn1 O2 2.134(3) . ? Mn1 O1 2.162(3) . ? Mn1 N1 2.221(3) . ? Mn1 O11 2.272(3) . ? Mn1 O15 2.308(3) . ? Mn1 O14 2.409(3) . ? Mn1 O12 2.421(3) . ? Mn2 O4 2.130(3) . ? Mn2 O3 2.149(3) . ? Mn2 N3 2.238(3) . ? Mn2 O21 2.274(3) . ? Mn2 O18 2.316(3) . ? Mn2 O17 2.346(3) . ? Mn2 O20 2.470(4) . ? C1 N1 1.344(5) . ? C1 C2 1.373(5) . ? C1 H1 0.9500 . ? C2 C3 1.393(5) . ? C2 H2 0.9500 . ? C3 C4 1.385(6) . ? C3 C8 1.490(6) . ? C4 C5 1.373(6) . ? C4 H4 0.9500 . ? C5 N1 1.350(5) . ? C5 H5 0.9500 . ? C6 N2 1.335(6) . ? C6 C7 1.381(6) . ? C6 H6 0.9500 . ? C7 C8 1.394(5) . ? C7 H7 0.9500 . ? C8 C9 1.379(6) . ? C9 C10 1.380(6) . ? C9 H9 0.9500 . ? C10 N2 1.351(5) . ? C10 C11 1.512(7) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 N3 1.345(5) . ? C12 C13 1.374(6) . ? C12 H12 0.9500 . ? C13 C14 1.396(5) . ? C13 H13 0.9500 . ? C14 C15 1.393(6) . ? C14 C19 1.489(6) . ? C15 C16 1.381(6) . ? C15 H15 0.9500 . ? C16 N3 1.346(5) . ? C16 H16 0.9500 . ? C17 N4 1.327(6) . ? C17 C18 1.386(6) . ? C17 H17 0.9500 . ? C18 C19 1.405(5) . ? C18 H18 0.9500 . ? C19 C20 1.384(6) . ? C20 C21 1.403(6) . ? C20 H20 0.9500 . ? C21 N4 1.346(5) . ? C21 C22 1.485(7) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N5 O13 1.229(5) . ? N5 O12 1.249(5) . ? N5 O11 1.274(4) . ? N6 O16 1.235(4) . ? N6 O15 1.243(5) . ? N6 O14 1.271(4) . ? N7 O19 1.220(5) . ? N7 O18 1.259(5) . ? N7 O17 1.280(4) . ? N8 O22 1.233(4) . ? N8 O21 1.253(5) . ? N8 O20 1.267(5) . ? O1 H1A 0.83(2) . ? O1 H1B 0.83(2) . ? O2 H2A 0.83(2) . ? O2 H2B 0.83(2) . ? O3 H3A 0.83(2) . ? O3 H3B 0.83(2) . ? O4 H4A 0.83(2) . ? O4 H4B 0.84(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 O2 Mn1 O1 170.58(12) . . ? O2 Mn1 N1 93.52(12) . . ? O1 Mn1 N1 91.82(13) . . ? O2 Mn1 O11 84.94(11) . . ? O1 Mn1 O11 85.98(12) . . ? N1 Mn1 O11 140.15(12) . . ? O2 Mn1 O15 97.63(11) . . ? O1 Mn1 O15 83.73(12) . . ? N1 Mn1 O15 136.51(13) . . ? O11 Mn1 O15 82.84(11) . . ? O2 Mn1 O14 94.29(12) . . ? O1 Mn1 O14 94.03(12) . . ? N1 Mn1 O14 83.42(12) . . ? O11 Mn1 O14 136.43(10) . . ? O15 Mn1 O14 54.00(10) . . ? O2 Mn1 O12 86.30(11) . . ? O1 Mn1 O12 86.37(12) . . ? N1 Mn1 O12 85.67(11) . . ? O11 Mn1 O12 54.49(10) . . ? O15 Mn1 O12 136.76(11) . . ? O14 Mn1 O12 169.08(10) . . ? O4 Mn2 O3 171.95(13) . . ? O4 Mn2 N3 92.23(12) . . ? O3 Mn2 N3 95.16(13) . . ? O4 Mn2 O21 85.68(12) . . ? O3 Mn2 O21 91.42(12) . . ? N3 Mn2 O21 134.24(12) . . ? O4 Mn2 O18 91.30(13) . . ? O3 Mn2 O18 85.99(12) . . ? N3 Mn2 O18 86.35(12) . . ? O21 Mn2 O18 139.35(11) . . ? O4 Mn2 O17 84.01(12) . . ? O3 Mn2 O17 88.23(12) . . ? N3 Mn2 O17 141.01(12) . . ? O21 Mn2 O17 84.31(10) . . ? O18 Mn2 O17 55.08(10) . . ? O4 Mn2 O20 90.91(13) . . ? O3 Mn2 O20 93.44(12) . . ? N3 Mn2 O20 80.61(12) . . ? O21 Mn2 O20 53.78(10) . . ? O18 Mn2 O20 166.84(11) . . ? O17 Mn2 O20 138.07(10) . . ? N1 C1 C2 123.1(4) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 118.7(4) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 118.8(4) . . ? C4 C3 C8 120.9(3) . . ? C2 C3 C8 120.4(4) . . ? C5 C4 C3 118.9(4) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 122.9(4) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? N2 C6 C7 123.1(4) . . ? N2 C6 H6 118.4 . . ? C7 C6 H6 118.4 . . ? C6 C7 C8 118.2(4) . . ? C6 C7 H7 120.9 . . ? C8 C7 H7 120.9 . . ? C9 C8 C7 118.7(4) . . ? C9 C8 C3 121.2(3) . . ? C7 C8 C3 120.1(4) . . ? C8 C9 C10 119.8(4) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? N2 C10 C9 121.6(4) . . ? N2 C10 C11 116.7(4) . . ? C9 C10 C11 121.7(4) . . ? 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 . . ? N3 C12 C13 124.0(4) . . ? N3 C12 H12 118.0 . . ? C13 C12 H12 118.0 . . ? C12 C13 C14 119.2(4) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C15 C14 C13 117.4(4) . . ? C15 C14 C19 121.5(3) . . ? C13 C14 C19 121.1(4) . . ? C16 C15 C14 119.2(4) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? N3 C16 C15 123.7(4) . . ? N3 C16 H16 118.1 . . ? C15 C16 H16 118.1 . . ? N4 C17 C18 124.0(4) . . ? N4 C17 H17 118.0 . . ? C18 C17 H17 118.0 . . ? C17 C18 C19 118.5(4) . . ? C17 C18 H18 120.8 . . ? C19 C18 H18 120.8 . . ? C20 C19 C18 117.5(4) . . ? C20 C19 C14 121.2(3) . . ? C18 C19 C14 121.3(4) . . ? C19 C20 C21 120.3(4) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? N4 C21 C20 121.4(4) . . ? N4 C21 C22 117.0(4) . . ? C20 C21 C22 121.6(4) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C1 N1 C5 117.6(4) . . ? C1 N1 Mn1 122.3(3) . . ? C5 N1 Mn1 120.0(3) . . ? C6 N2 C10 118.4(4) . . ? C12 N3 C16 116.3(4) . . ? C12 N3 Mn2 122.7(3) . . ? C16 N3 Mn2 120.0(3) . . ? C17 N4 C21 118.2(4) . . ? O13 N5 O12 122.0(4) . . ? O13 N5 O11 120.9(4) . . ? O12 N5 O11 117.1(4) . . ? O16 N6 O15 123.0(4) . . ? O16 N6 O14 120.1(4) . . ? O15 N6 O14 117.0(3) . . ? O19 N7 O18 123.6(4) . . ? O19 N7 O17 120.1(4) . . ? O18 N7 O17 116.3(4) . . ? O22 N8 O21 120.9(4) . . ? O22 N8 O20 121.7(4) . . ? O21 N8 O20 117.4(4) . . ? Mn1 O1 H1A 120(4) . . ? Mn1 O1 H1B 104(4) . . ? H1A O1 H1B 115(6) . . ? Mn1 O2 H2A 132(4) . . ? Mn1 O2 H2B 115(4) . . ? H2A O2 H2B 102(6) . . ? Mn2 O3 H3A 125(4) . . ? Mn2 O3 H3B 122(4) . . ? H3A O3 H3B 111(6) . . ? Mn2 O4 H4A 124(4) . . ? Mn2 O4 H4B 114(4) . . ? H4A O4 H4B 108(5) . . ? N5 O11 Mn1 97.4(2) . . ? N5 O12 Mn1 91.0(2) . . ? N6 O14 Mn1 91.3(2) . . ? N6 O15 Mn1 96.8(2) . . ? N7 O17 Mn2 93.3(2) . . ? N7 O18 Mn2 95.3(2) . . ? N8 O20 Mn2 89.3(2) . . ? N8 O21 Mn2 99.0(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -1.9(6) . . . . ? C1 C2 C3 C4 -1.3(5) . . . . ? C1 C2 C3 C8 179.1(3) . . . . ? C2 C3 C4 C5 3.0(5) . . . . ? C8 C3 C4 C5 -177.3(3) . . . . ? C3 C4 C5 N1 -1.9(6) . . . . ? N2 C6 C7 C8 -2.1(6) . . . . ? C6 C7 C8 C9 2.4(6) . . . . ? C6 C7 C8 C3 -176.7(3) . . . . ? C4 C3 C8 C9 142.2(4) . . . . ? C2 C3 C8 C9 -38.2(5) . . . . ? C4 C3 C8 C7 -38.8(5) . . . . ? C2 C3 C8 C7 140.9(4) . . . . ? C7 C8 C9 C10 -1.3(6) . . . . ? C3 C8 C9 C10 177.7(3) . . . . ? C8 C9 C10 N2 -0.1(6) . . . . ? C8 C9 C10 C11 179.0(4) . . . . ? N3 C12 C13 C14 1.9(6) . . . . ? C12 C13 C14 C15 1.2(6) . . . . ? C12 C13 C14 C19 -177.3(3) . . . . ? C13 C14 C15 C16 -3.5(6) . . . . ? C19 C14 C15 C16 175.0(4) . . . . ? C14 C15 C16 N3 3.2(6) . . . . ? N4 C17 C18 C19 2.2(6) . . . . ? C17 C18 C19 C20 -1.2(6) . . . . ? C17 C18 C19 C14 178.1(3) . . . . ? C15 C14 C19 C20 -139.3(4) . . . . ? C13 C14 C19 C20 39.1(6) . . . . ? C15 C14 C19 C18 41.4(6) . . . . ? C13 C14 C19 C18 -140.1(4) . . . . ? C18 C19 C20 C21 -1.3(6) . . . . ? C14 C19 C20 C21 179.4(4) . . . . ? C19 C20 C21 N4 3.1(6) . . . . ? C19 C20 C21 C22 -177.9(4) . . . . ? C2 C1 N1 C5 3.0(6) . . . . ? C2 C1 N1 Mn1 -172.7(3) . . . . ? C4 C5 N1 C1 -1.1(6) . . . . ? C4 C5 N1 Mn1 174.8(3) . . . . ? O2 Mn1 N1 C1 120.1(3) . . . . ? O1 Mn1 N1 C1 -67.6(3) . . . . ? O11 Mn1 N1 C1 -153.5(3) . . . . ? O15 Mn1 N1 C1 15.2(4) . . . . ? O14 Mn1 N1 C1 26.2(3) . . . . ? O12 Mn1 N1 C1 -153.8(3) . . . . ? O2 Mn1 N1 C5 -55.5(3) . . . . ? O1 Mn1 N1 C5 116.7(3) . . . . ? O11 Mn1 N1 C5 30.8(4) . . . . ? O15 Mn1 N1 C5 -160.5(3) . . . . ? O14 Mn1 N1 C5 -149.5(3) . . . . ? O12 Mn1 N1 C5 30.5(3) . . . . ? C7 C6 N2 C10 0.7(6) . . . . ? C9 C10 N2 C6 0.4(6) . . . . ? C11 C10 N2 C6 -178.8(4) . . . . ? C13 C12 N3 C16 -2.4(6) . . . . ? C13 C12 N3 Mn2 166.5(3) . . . . ? C15 C16 N3 C12 -0.2(6) . . . . ? C15 C16 N3 Mn2 -169.3(3) . . . . ? O4 Mn2 N3 C12 -119.9(3) . . . . ? O3 Mn2 N3 C12 63.3(3) . . . . ? O21 Mn2 N3 C12 -33.7(4) . . . . ? O18 Mn2 N3 C12 149.0(3) . . . . ? O17 Mn2 N3 C12 156.9(3) . . . . ? O20 Mn2 N3 C12 -29.3(3) . . . . ? O4 Mn2 N3 C16 48.5(3) . . . . ? O3 Mn2 N3 C16 -128.3(3) . . . . ? O21 Mn2 N3 C16 134.7(3) . . . . ? O18 Mn2 N3 C16 -42.6(3) . . . . ? O17 Mn2 N3 C16 -34.7(4) . . . . ? O20 Mn2 N3 C16 139.1(3) . . . . ? C18 C17 N4 C21 -0.5(6) . . . . ? C20 C21 N4 C17 -2.2(6) . . . . ? C22 C21 N4 C17 178.8(4) . . . . ? O13 N5 O11 Mn1 178.9(3) . . . . ? O12 N5 O11 Mn1 -1.7(4) . . . . ? O2 Mn1 O11 N5 90.0(2) . . . . ? O1 Mn1 O11 N5 -87.5(2) . . . . ? N1 Mn1 O11 N5 0.6(3) . . . . ? O15 Mn1 O11 N5 -171.6(2) . . . . ? O14 Mn1 O11 N5 -179.1(2) . . . . ? O12 Mn1 O11 N5 0.9(2) . . . . ? O13 N5 O12 Mn1 -179.0(3) . . . . ? O11 N5 O12 Mn1 1.5(3) . . . . ? O2 Mn1 O12 N5 -87.4(2) . . . . ? O1 Mn1 O12 N5 86.7(2) . . . . ? N1 Mn1 O12 N5 178.8(3) . . . . ? O11 Mn1 O12 N5 -0.9(2) . . . . ? O15 Mn1 O12 N5 9.8(3) . . . . ? O14 Mn1 O12 N5 179.1(5) . . . . ? O16 N6 O14 Mn1 170.3(3) . . . . ? O15 N6 O14 Mn1 -9.4(3) . . . . ? O2 Mn1 O14 N6 101.9(2) . . . . ? O1 Mn1 O14 N6 -73.7(2) . . . . ? N1 Mn1 O14 N6 -165.0(2) . . . . ? O11 Mn1 O14 N6 14.7(3) . . . . ? O15 Mn1 O14 N6 5.6(2) . . . . ? O12 Mn1 O14 N6 -165.4(5) . . . . ? O16 N6 O15 Mn1 -169.8(3) . . . . ? O14 N6 O15 Mn1 9.9(4) . . . . ? O2 Mn1 O15 N6 -95.5(2) . . . . ? O1 Mn1 O15 N6 93.9(2) . . . . ? N1 Mn1 O15 N6 7.9(3) . . . . ? O11 Mn1 O15 N6 -179.4(2) . . . . ? O14 Mn1 O15 N6 -5.7(2) . . . . ? O12 Mn1 O15 N6 171.8(2) . . . . ? O19 N7 O17 Mn2 177.8(4) . . . . ? O18 N7 O17 Mn2 -1.6(4) . . . . ? O4 Mn2 O17 N7 -94.9(2) . . . . ? O3 Mn2 O17 N7 87.3(2) . . . . ? N3 Mn2 O17 N7 -8.7(3) . . . . ? O21 Mn2 O17 N7 178.9(2) . . . . ? O18 Mn2 O17 N7 1.0(2) . . . . ? O20 Mn2 O17 N7 -179.5(2) . . . . ? O19 N7 O18 Mn2 -177.8(4) . . . . ? O17 N7 O18 Mn2 1.6(4) . . . . ? O4 Mn2 O18 N7 80.8(3) . . . . ? O3 Mn2 O18 N7 -91.6(3) . . . . ? N3 Mn2 O18 N7 173.0(3) . . . . ? O21 Mn2 O18 N7 -4.1(3) . . . . ? O17 Mn2 O18 N7 -1.0(2) . . . . ? O20 Mn2 O18 N7 -179.6(5) . . . . ? O22 N8 O20 Mn2 173.2(3) . . . . ? O21 N8 O20 Mn2 -7.0(3) . . . . ? O4 Mn2 O20 N8 -79.7(2) . . . . ? O3 Mn2 O20 N8 93.5(2) . . . . ? N3 Mn2 O20 N8 -171.8(3) . . . . ? O21 Mn2 O20 N8 4.2(2) . . . . ? O18 Mn2 O20 N8 -179.4(5) . . . . ? O17 Mn2 O20 N8 2.3(3) . . . . ? O22 N8 O21 Mn2 -172.5(3) . . . . ? O20 N8 O21 Mn2 7.7(4) . . . . ? O4 Mn2 O21 N8 90.0(2) . . . . ? O3 Mn2 O21 N8 -97.6(2) . . . . ? N3 Mn2 O21 N8 1.0(3) . . . . ? O18 Mn2 O21 N8 176.9(2) . . . . ? O17 Mn2 O21 N8 174.4(2) . . . . ? O20 Mn2 O21 N8 -4.3(2) . . . . ? 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 O1 H1A O17 0.83(2) 2.11(3) 2.929(5) 167(6) 1_545 O1 H1A O19 0.83(2) 2.57(5) 3.149(5) 128(5) 1_545 O1 H1B O20 0.83(2) 2.26(4) 3.000(5) 147(5) 4_565 O2 H2A N2 0.83(2) 1.93(3) 2.718(4) 159(6) 2_656 O2 H2B O22 0.83(2) 2.11(2) 2.930(4) 170(5) 4_575 O3 H3A O13 0.83(2) 2.02(3) 2.795(5) 155(5) 4_566 O3 H3A O11 0.83(2) 2.56(4) 3.232(5) 140(5) 4_566 O3 H3A N5 0.83(2) 2.61(3) 3.392(5) 157(5) 4_566 O3 H3B O14 0.83(2) 2.05(2) 2.877(5) 173(6) . O4 H4A N4 0.83(2) 1.88(3) 2.689(5) 164(6) 2_556 O4 H4B O16 0.84(2) 2.25(3) 3.044(5) 159(5) 1_565 O4 H4B O14 0.84(2) 2.53(4) 3.237(5) 143(5) 1_565 O4 H4B N6 0.84(2) 2.67(2) 3.502(5) 171(5) 1_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.15 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.508 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.073 # Attachment '2.cif' data_cl44bt _database_code_depnum_ccdc_archive 'CCDC 267237' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H30 Mn N6 O2, 2(Cl O4)' _chemical_formula_sum 'C26 H30 Cl2 Mn N6 O10' _chemical_formula_weight 712.40 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.1520(8) _cell_length_b 13.1262(9) _cell_length_c 11.6168(8) _cell_angle_alpha 90.00 _cell_angle_beta 112.8550(10) _cell_angle_gamma 90.00 _cell_volume 1567.00(19) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 5526 _cell_measurement_theta_min 2.517 _cell_measurement_theta_max 26.397 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 734 _exptl_absorpt_coefficient_mu 0.656 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 16385 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.40 _reflns_number_total 3214 _reflns_number_gt 2918 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART NT V5.625 (Bruker, 1998)' _computing_cell_refinement 'SAINT+ NT V6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT+ NT V6.22' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V6.1 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0540P)^2^+0.9746P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3214 _refine_ls_number_parameters 215 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1032 _refine_ls_wR_factor_gt 0.1008 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.052 _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 0.0000 0.0000 0.5000 0.02360(13) Uani 1 2 d S . . C1 C 0.2875(2) 0.08481(17) 0.63548(18) 0.0313(5) Uani 1 1 d . . . H1 H 0.2863 0.0783 0.5536 0.038 Uiso 1 1 calc R . . C2 C 0.40466(19) 0.10569(17) 0.73208(18) 0.0305(4) Uani 1 1 d . . . H2 H 0.4814 0.1126 0.7158 0.037 Uiso 1 1 calc R . . C3 C 0.41077(18) 0.11659(14) 0.85342(17) 0.0228(4) Uani 1 1 d . . . C4 C 0.29296(19) 0.10924(15) 0.86831(18) 0.0269(4) Uani 1 1 d . . . H4 H 0.2904 0.1189 0.9484 0.032 Uiso 1 1 calc R . . C5 C 0.18007(19) 0.08784(16) 0.76664(18) 0.0285(4) Uani 1 1 d . . . H5 H 0.1012 0.0832 0.7795 0.034 Uiso 1 1 calc R . . C6 C 0.6623(2) 0.15775(16) 1.17877(19) 0.0322(5) Uani 1 1 d . . . H6 H 0.6646 0.1693 1.2603 0.039 Uiso 1 1 calc R . . C7 C 0.5421(2) 0.14925(16) 1.08169(18) 0.0305(4) Uani 1 1 d . . . H7 H 0.4645 0.1554 1.0966 0.037 Uiso 1 1 calc R . . C8 C 0.53665(18) 0.13146(14) 0.96101(17) 0.0235(4) Uani 1 1 d . . . C9 C 0.6539(2) 0.12480(16) 0.94668(18) 0.0307(4) Uani 1 1 d . . . H9 H 0.6544 0.1130 0.8662 0.037 Uiso 1 1 calc R . . C10 C 0.7713(2) 0.13528(17) 1.0494(2) 0.0342(5) Uani 1 1 d . . . C11 C 0.8983(2) 0.1288(3) 1.0351(3) 0.0589(8) Uani 1 1 d . . . H11A H 0.9695 0.1295 1.1178 0.088 Uiso 1 1 calc R . . H11B H 0.9072 0.1871 0.9864 0.088 Uiso 1 1 calc R . . H11C H 0.9017 0.0654 0.9918 0.088 Uiso 1 1 calc R . . C12 C -0.2282(2) 0.13390(17) 0.5558(2) 0.0336(5) Uani 1 1 d . . . C13 C -0.3449(2) 0.1795(2) 0.5606(3) 0.0468(6) Uani 1 1 d . . . H13A H -0.3578 0.2474 0.5225 0.070 Uiso 1 1 calc R . . H13B H -0.3355 0.1854 0.6478 0.070 Uiso 1 1 calc R . . H13C H -0.4203 0.1366 0.5146 0.070 Uiso 1 1 calc R . . N1 N 0.17545(15) 0.07324(13) 0.65082(14) 0.0263(4) Uani 1 1 d . . . N2 N 0.77508(16) 0.15067(13) 1.16504(15) 0.0318(4) Uani 1 1 d . . . N3 N -0.13907(18) 0.09736(15) 0.54949(18) 0.0375(4) Uani 1 1 d . . . O1 O -0.00030(15) 0.11280(12) 0.36653(14) 0.0341(4) Uani 1 1 d D . . H1A H 0.062(2) 0.127(2) 0.354(3) 0.053(9) Uiso 1 1 d D . . H1B H -0.064(2) 0.126(2) 0.306(2) 0.061(9) Uiso 1 1 d D . . Cl1 Cl 0.31355(5) 0.12251(5) 0.28408(5) 0.03930(16) Uani 1 1 d . . . O11 O 0.21988(17) 0.17246(14) 0.32128(17) 0.0480(4) Uani 1 1 d . . . O12 O 0.3794(2) 0.04629(18) 0.3739(2) 0.0705(6) Uani 1 1 d . . . O13 O 0.40607(18) 0.19786(16) 0.28107(19) 0.0582(5) Uani 1 1 d . . . O14 O 0.2509(2) 0.08103(19) 0.1626(2) 0.0733(6) Uani 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 Mn1 0.0165(2) 0.0305(2) 0.0207(2) -0.00079(16) 0.00383(15) -0.00074(15) C1 0.0278(10) 0.0448(12) 0.0201(9) -0.0013(8) 0.0078(8) -0.0087(9) C2 0.0224(10) 0.0453(12) 0.0241(9) -0.0021(9) 0.0092(8) -0.0072(9) C3 0.0224(9) 0.0211(9) 0.0223(9) 0.0010(7) 0.0058(7) -0.0011(7) C4 0.0261(10) 0.0312(10) 0.0237(9) -0.0036(8) 0.0100(8) -0.0007(8) C5 0.0215(9) 0.0326(10) 0.0310(10) -0.0033(8) 0.0096(8) -0.0008(8) C6 0.0338(11) 0.0325(11) 0.0232(9) -0.0037(8) 0.0032(8) 0.0019(9) C7 0.0275(10) 0.0364(11) 0.0249(9) -0.0034(8) 0.0071(8) 0.0033(8) C8 0.0227(9) 0.0206(9) 0.0227(9) 0.0016(7) 0.0040(7) -0.0012(7) C9 0.0250(10) 0.0402(11) 0.0241(9) 0.0041(8) 0.0066(8) -0.0031(8) C10 0.0244(10) 0.0413(12) 0.0311(10) 0.0077(9) 0.0044(8) -0.0055(9) C11 0.0252(12) 0.104(2) 0.0443(14) 0.0111(15) 0.0095(11) -0.0068(13) C12 0.0274(11) 0.0366(11) 0.0353(11) -0.0068(9) 0.0104(9) -0.0023(9) C13 0.0304(12) 0.0474(14) 0.0642(16) -0.0096(12) 0.0201(11) 0.0040(10) N1 0.0214(8) 0.0295(8) 0.0236(8) 0.0016(6) 0.0039(6) -0.0023(7) N2 0.0276(9) 0.0301(9) 0.0269(8) 0.0035(7) -0.0011(7) -0.0047(7) N3 0.0304(10) 0.0410(10) 0.0407(10) -0.0074(8) 0.0135(8) -0.0005(8) O1 0.0214(7) 0.0459(9) 0.0277(8) 0.0089(6) 0.0017(6) -0.0044(7) Cl1 0.0352(3) 0.0502(3) 0.0359(3) 0.0042(2) 0.0175(2) 0.0051(2) O11 0.0433(10) 0.0544(11) 0.0584(11) -0.0039(9) 0.0331(9) -0.0035(8) O12 0.0590(13) 0.0722(14) 0.0798(15) 0.0354(12) 0.0264(11) 0.0149(11) O13 0.0481(11) 0.0729(13) 0.0650(12) 0.0088(10) 0.0343(10) -0.0070(10) O14 0.0760(15) 0.0839(16) 0.0554(12) -0.0254(11) 0.0203(11) 0.0031(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 Mn1 O1 2.1430(15) 3_556 ? Mn1 O1 2.1430(16) . ? Mn1 N3 2.2498(19) 3_556 ? Mn1 N3 2.2498(19) . ? Mn1 N1 2.2714(16) . ? Mn1 N1 2.2714(15) 3_556 ? C1 N1 1.338(3) . ? C1 C2 1.379(3) . ? C1 H1 0.9500 . ? C2 C3 1.392(3) . ? C2 H2 0.9500 . ? C3 C4 1.394(3) . ? C3 C8 1.486(2) . ? C4 C5 1.380(3) . ? C4 H4 0.9500 . ? C5 N1 1.340(3) . ? C5 H5 0.9500 . ? C6 N2 1.331(3) . ? C6 C7 1.381(3) . ? C6 H6 0.9500 . ? C7 C8 1.399(3) . ? C7 H7 0.9500 . ? C8 C9 1.383(3) . ? C9 C10 1.394(3) . ? C9 H9 0.9500 . ? C10 N2 1.343(3) . ? C10 C11 1.491(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 N3 1.131(3) . ? C12 C13 1.453(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? O1 H1A 0.79(2) . ? O1 H1B 0.81(2) . ? Cl1 O14 1.418(2) . ? Cl1 O12 1.426(2) . ? Cl1 O11 1.4348(17) . ? Cl1 O13 1.4395(19) . ? 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 O1 180.0 3_556 . ? O1 Mn1 N3 89.14(7) 3_556 3_556 ? O1 Mn1 N3 90.86(7) . 3_556 ? O1 Mn1 N3 90.86(7) 3_556 . ? O1 Mn1 N3 89.14(7) . . ? N3 Mn1 N3 180.0 3_556 . ? O1 Mn1 N1 88.60(6) 3_556 . ? O1 Mn1 N1 91.40(6) . . ? N3 Mn1 N1 87.98(6) 3_556 . ? N3 Mn1 N1 92.02(6) . . ? O1 Mn1 N1 91.40(6) 3_556 3_556 ? O1 Mn1 N1 88.60(6) . 3_556 ? N3 Mn1 N1 92.02(6) 3_556 3_556 ? N3 Mn1 N1 87.98(6) . 3_556 ? N1 Mn1 N1 180.0 . 3_556 ? N1 C1 C2 123.57(18) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C1 C2 C3 120.18(19) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C4 116.16(17) . . ? C2 C3 C8 121.60(17) . . ? C4 C3 C8 122.20(17) . . ? C5 C4 C3 119.91(18) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? N1 C5 C4 123.72(18) . . ? N1 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? N2 C6 C7 123.98(19) . . ? N2 C6 H6 118.0 . . ? C7 C6 H6 118.0 . . ? C6 C7 C8 118.88(19) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? C9 C8 C7 117.11(17) . . ? C9 C8 C3 121.25(17) . . ? C7 C8 C3 121.61(17) . . ? C8 C9 C10 120.54(19) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? N2 C10 C9 121.7(2) . . ? N2 C10 C11 117.23(19) . . ? C9 C10 C11 121.1(2) . . ? 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 . . ? N3 C12 C13 178.4(2) . . ? 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 . . ? C1 N1 C5 116.35(16) . . ? C1 N1 Mn1 120.98(13) . . ? C5 N1 Mn1 121.38(13) . . ? C6 N2 C10 117.79(17) . . ? C12 N3 Mn1 165.36(18) . . ? Mn1 O1 H1A 123(2) . . ? Mn1 O1 H1B 123(2) . . ? H1A O1 H1B 109(3) . . ? O14 Cl1 O12 111.92(15) . . ? O14 Cl1 O11 109.89(13) . . ? O12 Cl1 O11 109.20(13) . . ? O14 Cl1 O13 108.70(14) . . ? O12 Cl1 O13 109.22(13) . . ? O11 Cl1 O13 107.81(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.5(3) . . . . ? C1 C2 C3 C4 -2.5(3) . . . . ? C1 C2 C3 C8 175.41(19) . . . . ? C2 C3 C4 C5 2.7(3) . . . . ? C8 C3 C4 C5 -175.16(18) . . . . ? C3 C4 C5 N1 -0.1(3) . . . . ? N2 C6 C7 C8 0.4(3) . . . . ? C6 C7 C8 C9 -0.8(3) . . . . ? C6 C7 C8 C3 177.01(18) . . . . ? C2 C3 C8 C9 -6.6(3) . . . . ? C4 C3 C8 C9 171.13(19) . . . . ? C2 C3 C8 C7 175.63(19) . . . . ? C4 C3 C8 C7 -6.6(3) . . . . ? C7 C8 C9 C10 0.2(3) . . . . ? C3 C8 C9 C10 -177.66(19) . . . . ? C8 C9 C10 N2 0.9(3) . . . . ? C8 C9 C10 C11 -179.7(2) . . . . ? C2 C1 N1 C5 3.1(3) . . . . ? C2 C1 N1 Mn1 -164.09(17) . . . . ? C4 C5 N1 C1 -2.8(3) . . . . ? C4 C5 N1 Mn1 164.29(16) . . . . ? O1 Mn1 N1 C1 121.55(16) 3_556 . . . ? O1 Mn1 N1 C1 -58.46(16) . . . . ? N3 Mn1 N1 C1 32.36(16) 3_556 . . . ? N3 Mn1 N1 C1 -147.64(16) . . . . ? O1 Mn1 N1 C5 -45.00(15) 3_556 . . . ? O1 Mn1 N1 C5 135.00(15) . . . . ? N3 Mn1 N1 C5 -134.18(16) 3_556 . . . ? N3 Mn1 N1 C5 45.82(16) . . . . ? C7 C6 N2 C10 0.6(3) . . . . ? C9 C10 N2 C6 -1.3(3) . . . . ? C11 C10 N2 C6 179.3(2) . . . . ? O1 Mn1 N3 C12 -86.8(8) 3_556 . . . ? O1 Mn1 N3 C12 93.2(8) . . . . ? N1 Mn1 N3 C12 -175.5(8) . . . . ? N1 Mn1 N3 C12 4.5(8) 3_556 . . . ? 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 O1 H1A O11 0.79(2) 2.02(2) 2.814(2) 176(3) . O1 H1B N2 0.81(2) 1.92(2) 2.729(2) 175(3) 1_454 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.582 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.063 # Attachment '3.cif' data_mn44coot _database_code_depnum_ccdc_archive 'CCDC 267238' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 Mn N4 O6, 2(H2 O)' _chemical_formula_sum 'C22 H22 Mn N4 O8' _chemical_formula_weight 525.38 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'I 2/a' _symmetry_space_group_name_Hall '-I 2ya' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 19.3775(10) _cell_length_b 7.6358(4) _cell_length_c 15.1202(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.3050(10) _cell_angle_gamma 90.00 _cell_volume 2233.50(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 7099 _cell_measurement_theta_min 2.698 _cell_measurement_theta_max 26.357 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 0.649 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 11586 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2292 _reflns_number_gt 2060 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART NT V5.625 (Bruker, 1998)' _computing_cell_refinement 'SAINT+ NT V6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT+ NT V6.22' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V6.1 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V6.1' _refine_special_details ; 6 same O-H distance restraints (SHELX SADI) for waters. 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^)+(0.0493P)^2^+0.6720P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2292 _refine_ls_number_parameters 182 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0391 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0860 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.044 _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 0.2500 0.30503(5) 0.5000 0.02257(13) Uani 1 2 d S . . C1 C 0.33547(9) 0.2023(2) 0.34549(11) 0.0218(4) Uani 1 1 d . . . C2 C 0.38400(9) 0.2037(2) 0.28171(11) 0.0228(4) Uani 1 1 d . . . H2 H 0.3739 0.1503 0.2257 0.023(5) Uiso 1 1 calc R . . C3 C 0.44748(9) 0.2838(2) 0.30041(11) 0.0237(4) Uani 1 1 d . . . C4 C 0.45928(9) 0.3619(2) 0.38295(12) 0.0289(4) Uani 1 1 d . . . H4 H 0.5026 0.4147 0.3989 0.037(5) Uiso 1 1 calc R . . C5 C 0.40714(9) 0.3618(2) 0.44150(12) 0.0294(4) Uani 1 1 d . . . H5 H 0.4149 0.4202 0.4967 0.030(5) Uiso 1 1 calc R . . C6 C 0.26701(9) 0.1064(2) 0.33154(11) 0.0224(4) Uani 1 1 d . . . C7 C 0.61837(10) 0.2534(2) 0.19476(13) 0.0298(4) Uani 1 1 d . . . H7 H 0.6648 0.2236 0.2118 0.024(5) Uiso 1 1 calc R . . C8 C 0.56977(9) 0.2485(2) 0.25852(12) 0.0279(4) Uani 1 1 d . . . H8 H 0.5831 0.2188 0.3181 0.027(5) Uiso 1 1 calc R . . C9 C 0.50127(9) 0.2876(2) 0.23419(12) 0.0245(4) Uani 1 1 d . . . C10 C 0.48433(10) 0.3306(2) 0.14632(12) 0.0283(4) Uani 1 1 d . . . H10 H 0.4380 0.3560 0.1267 0.024(5) Uiso 1 1 calc R . . C11 C 0.53710(10) 0.3353(2) 0.08795(13) 0.0314(4) Uani 1 1 d . . . H11 H 0.5255 0.3670 0.0282 0.036(5) Uiso 1 1 calc R . . N1 N 0.34627(8) 0.28326(18) 0.42410(9) 0.0237(3) Uani 1 1 d . . . N2 N 0.60304(8) 0.2980(2) 0.11059(11) 0.0312(4) Uani 1 1 d . . . O1 O 0.22685(6) 0.11722(16) 0.39515(8) 0.0268(3) Uani 1 1 d . . . O2 O 0.25509(6) 0.02407(16) 0.26193(7) 0.0269(3) Uani 1 1 d . . . O3 O 0.20491(8) 0.49890(18) 0.40918(9) 0.0345(3) Uani 1 1 d D . . H3A H 0.1984(15) 0.600(2) 0.4227(18) 0.070(9) Uiso 1 1 d D . . H3B H 0.2153(11) 0.499(3) 0.3590(10) 0.041(6) Uiso 1 1 d D . . O4 O 0.15948(7) 0.81736(17) 0.44599(10) 0.0328(3) Uani 1 1 d D . . H4A H 0.1805(11) 0.904(2) 0.4332(15) 0.049(7) Uiso 1 1 d D . . H4B H 0.1562(14) 0.824(3) 0.4987(10) 0.057(8) 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 Mn1 0.0285(2) 0.0238(2) 0.0161(2) 0.000 0.00778(14) 0.000 C1 0.0254(9) 0.0209(8) 0.0194(8) 0.0026(6) 0.0035(6) 0.0036(7) C2 0.0277(9) 0.0229(8) 0.0183(8) 0.0008(6) 0.0044(7) 0.0033(7) C3 0.0274(9) 0.0221(8) 0.0219(9) 0.0031(7) 0.0047(7) 0.0021(7) C4 0.0281(9) 0.0324(9) 0.0262(9) -0.0013(8) 0.0022(7) -0.0050(8) C5 0.0343(10) 0.0339(9) 0.0200(9) -0.0044(7) 0.0011(7) -0.0020(8) C6 0.0274(9) 0.0214(8) 0.0188(8) 0.0028(7) 0.0040(7) 0.0028(7) C7 0.0245(9) 0.0288(9) 0.0364(11) -0.0017(8) 0.0056(8) -0.0037(7) C8 0.0278(9) 0.0271(9) 0.0290(10) -0.0003(7) 0.0030(7) -0.0039(7) C9 0.0279(9) 0.0214(9) 0.0248(9) -0.0011(7) 0.0064(7) -0.0027(7) C10 0.0286(9) 0.0295(9) 0.0271(9) 0.0002(7) 0.0042(7) 0.0010(7) C11 0.0400(11) 0.0299(10) 0.0250(10) 0.0011(7) 0.0077(8) -0.0016(8) N1 0.0292(8) 0.0250(7) 0.0171(7) 0.0000(6) 0.0039(6) 0.0016(6) N2 0.0325(8) 0.0284(8) 0.0339(9) -0.0031(7) 0.0119(7) -0.0043(7) O1 0.0311(6) 0.0285(6) 0.0220(6) -0.0031(5) 0.0110(5) -0.0047(5) O2 0.0284(6) 0.0321(6) 0.0206(6) -0.0052(5) 0.0048(5) -0.0026(5) O3 0.0550(9) 0.0306(7) 0.0189(7) 0.0023(6) 0.0101(6) 0.0104(7) O4 0.0416(8) 0.0292(7) 0.0289(8) -0.0028(6) 0.0116(6) -0.0067(6) _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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 6.7471 (0.0125) x - 6.5313 (0.0030) y + 5.4865 (0.0098) z = 2.8188 (0.0066) * -0.0058 (0.0011) N1 * 0.0186 (0.0011) C1 * -0.0127 (0.0011) C2 * -0.0048 (0.0012) C3 * 0.0172 (0.0013) C4 * -0.0124 (0.0013) C5 Rms deviation of fitted atoms = 0.0130 - 0.9857 (0.0100) x + 7.1746 (0.0026) y + 5.1536 (0.0146) z = 2.4188 (0.0072) Angle to previous plane (with approximate esd) = 46.24 ( 0.05 ) * -0.3050 (0.0012) N2 * -0.2102 (0.0006) C6 * -0.2063 (0.0014) C7 * 0.1348 (0.0013) C8 * 0.3572 (0.0015) C9 * 0.2295 (0.0012) C10 Rms deviation of fitted atoms = 0.2511 6.7471 (0.0125) x - 6.5313 (0.0030) y + 5.4865 (0.0098) z = 2.8188 (0.0066) Angle to previous plane (with approximate esd) = 46.24 ( 0.05 ) * -0.0058 (0.0011) N1 * 0.0186 (0.0011) C1 * -0.0127 (0.0011) C2 * -0.0048 (0.0012) C3 * 0.0172 (0.0013) C4 * -0.0124 (0.0013) C5 Rms deviation of fitted atoms = 0.0130 6.7471 (0.0126) x + 6.5313 (0.0030) y + 5.4865 (0.0098) z = 6.0412 (0.0057) Angle to previous plane (with approximate esd) = 62.40 ( 0.04 ) * 0.0058 (0.0011) N1_$4 * -0.0186 (0.0011) C1_$4 * 0.0127 (0.0011) C2_$4 * 0.0048 (0.0012) C3_$4 * -0.0172 (0.0013) C4_$4 * 0.0124 (0.0013) C5_$4 Rms deviation of fitted atoms = 0.0130 ; 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 2.1654(12) . ? Mn1 O1 2.1655(12) 2_556 ? Mn1 O3 2.1684(14) . ? Mn1 O3 2.1684(14) 2_556 ? Mn1 N1 2.2520(14) 2_556 ? Mn1 N1 2.2520(14) . ? C1 N1 1.345(2) . ? C1 C2 1.385(2) . ? C1 C6 1.520(2) . ? C2 C3 1.388(2) . ? C2 H2 0.9500 . ? C3 C4 1.390(3) . ? C3 C9 1.487(2) . ? C4 C5 1.381(3) . ? C4 H4 0.9500 . ? C5 N1 1.336(2) . ? C5 H5 0.9500 . ? C6 O2 1.236(2) . ? C6 O1 1.274(2) . ? C7 N2 1.334(3) . ? C7 C8 1.387(3) . ? C7 H7 0.9500 . ? C8 C9 1.389(3) . ? C8 H8 0.9500 . ? C9 C10 1.389(3) . ? C10 C11 1.389(3) . ? C10 H10 0.9500 . ? C11 N2 1.334(3) . ? C11 H11 0.9500 . ? O3 H3A 0.809(14) . ? O3 H3B 0.796(13) . ? O4 H4A 0.808(14) . ? O4 H4B 0.805(14) . ? 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 O1 97.05(7) . 2_556 ? O1 Mn1 O3 85.96(5) . . ? O1 Mn1 O3 167.06(5) 2_556 . ? O1 Mn1 O3 167.07(5) . 2_556 ? O1 Mn1 O3 85.96(5) 2_556 2_556 ? O3 Mn1 O3 93.90(8) . 2_556 ? O1 Mn1 N1 100.46(5) . 2_556 ? O1 Mn1 N1 73.78(5) 2_556 2_556 ? O3 Mn1 N1 93.31(5) . 2_556 ? O3 Mn1 N1 92.46(5) 2_556 2_556 ? O1 Mn1 N1 73.78(5) . . ? O1 Mn1 N1 100.46(5) 2_556 . ? O3 Mn1 N1 92.47(5) . . ? O3 Mn1 N1 93.31(5) 2_556 . ? N1 Mn1 N1 171.53(7) 2_556 . ? N1 C1 C2 122.31(16) . . ? N1 C1 C6 115.73(14) . . ? C2 C1 C6 121.96(15) . . ? C1 C2 C3 119.39(16) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C2 C3 C4 118.02(16) . . ? C2 C3 C9 121.26(15) . . ? C4 C3 C9 120.72(16) . . ? C5 C4 C3 119.12(16) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? N1 C5 C4 122.97(16) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? O2 C6 O1 125.69(16) . . ? O2 C6 C1 118.82(14) . . ? O1 C6 C1 115.48(14) . . ? N2 C7 C8 123.18(17) . . ? N2 C7 H7 118.4 . . ? C8 C7 H7 118.4 . . ? C7 C8 C9 119.15(17) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C8 C9 C10 118.25(16) . . ? C8 C9 C3 120.92(16) . . ? C10 C9 C3 120.83(16) . . ? C11 C10 C9 118.15(17) . . ? C11 C10 H10 120.9 . . ? C9 C10 H10 120.9 . . ? N2 C11 C10 124.09(18) . . ? N2 C11 H11 118.0 . . ? C10 C11 H11 118.0 . . ? C5 N1 C1 118.08(14) . . ? C5 N1 Mn1 127.91(11) . . ? C1 N1 Mn1 113.14(11) . . ? C7 N2 C11 117.16(16) . . ? C6 O1 Mn1 119.07(11) . . ? Mn1 O3 H3A 124(2) . . ? Mn1 O3 H3B 119.2(16) . . ? H3A O3 H3B 107(2) . . ? H4A O4 H4B 105(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 3.1(2) . . . . ? C6 C1 C2 C3 -175.77(15) . . . . ? C1 C2 C3 C4 -0.8(2) . . . . ? C1 C2 C3 C9 179.66(15) . . . . ? C2 C3 C4 C5 -2.0(3) . . . . ? C9 C3 C4 C5 177.50(16) . . . . ? C3 C4 C5 N1 2.9(3) . . . . ? N1 C1 C6 O2 -177.40(14) . . . . ? C2 C1 C6 O2 1.6(2) . . . . ? N1 C1 C6 O1 1.7(2) . . . . ? C2 C1 C6 O1 -179.32(15) . . . . ? N2 C7 C8 C9 1.6(3) . . . . ? C7 C8 C9 C10 -0.1(3) . . . . ? C7 C8 C9 C3 179.97(16) . . . . ? C2 C3 C9 C8 -134.57(18) . . . . ? C4 C3 C9 C8 45.9(2) . . . . ? C2 C3 C9 C10 45.5(2) . . . . ? C4 C3 C9 C10 -133.99(19) . . . . ? C8 C9 C10 C11 -1.2(3) . . . . ? C3 C9 C10 C11 178.73(16) . . . . ? C9 C10 C11 N2 1.2(3) . . . . ? C4 C5 N1 C1 -0.6(3) . . . . ? C4 C5 N1 Mn1 -169.23(14) . . . . ? C2 C1 N1 C5 -2.4(2) . . . . ? C6 C1 N1 C5 176.56(15) . . . . ? C2 C1 N1 Mn1 167.82(12) . . . . ? C6 C1 N1 Mn1 -13.20(17) . . . . ? O1 Mn1 N1 C5 -176.84(16) . . . . ? O1 Mn1 N1 C5 -82.46(15) 2_556 . . . ? O3 Mn1 N1 C5 98.09(15) . . . . ? O3 Mn1 N1 C5 4.04(15) 2_556 . . . ? O1 Mn1 N1 C1 14.09(11) . . . . ? O1 Mn1 N1 C1 108.47(11) 2_556 . . . ? O3 Mn1 N1 C1 -70.98(12) . . . . ? O3 Mn1 N1 C1 -165.03(11) 2_556 . . . ? C8 C7 N2 C11 -1.5(3) . . . . ? C10 C11 N2 C7 0.1(3) . . . . ? O2 C6 O1 Mn1 -169.17(13) . . . . ? C1 C6 O1 Mn1 11.81(18) . . . . ? O1 Mn1 O1 C6 -113.09(13) 2_556 . . . ? O3 Mn1 O1 C6 79.56(12) . . . . ? O3 Mn1 O1 C6 -10.3(3) 2_556 . . . ? N1 Mn1 O1 C6 172.18(12) 2_556 . . . ? N1 Mn1 O1 C6 -14.20(12) . . . . ? 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 H3A O4 0.809(14) 1.866(16) 2.6560(19) 165(3) . O3 H3B O2 0.796(13) 1.956(14) 2.7490(18) 174(2) 7 O4 H4A O1 0.808(14) 1.960(14) 2.7665(18) 176(2) 1_565 O4 H4B N2 0.805(14) 2.041(17) 2.780(2) 152(3) 3_455 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.321 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.058 # Attachment '4.cif' data_c12171m _database_code_depnum_ccdc_archive 'CCDC 267239' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 N4 O6 Zn, 2(H2 O)' _chemical_formula_sum 'C22 H22 N4 O8 Zn' _chemical_formula_weight 535.81 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'I 2/a' _symmetry_space_group_name_Hall '-I 2ya' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 19.4456(12) _cell_length_b 7.6438(4) _cell_length_c 14.8027(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.5820(10) _cell_angle_gamma 90.00 _cell_volume 2195.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 6439 _cell_measurement_theta_min 2.758 _cell_measurement_theta_max 26.358 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.621 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 1.178 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 8881 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2263 _reflns_number_gt 2063 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART NT V5.625 (Bruker, 1998)' _computing_cell_refinement 'SAINT+ NT V6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT+ NT V6.22' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V6.1 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0461P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2263 _refine_ls_number_parameters 182 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0302 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0753 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 1.077 _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 Zn1 Zn 0.2500 0.30577(3) 0.5000 0.01988(11) Uani 1 2 d S . . C1 C 0.33109(9) 0.20437(19) 0.34908(11) 0.0198(3) Uani 1 1 d . . . C2 C 0.38022(9) 0.20345(19) 0.28527(11) 0.0205(3) Uani 1 1 d . . . H2 H 0.3713 0.1461 0.2288 0.020(4) Uiso 1 1 calc R . . C3 C 0.44286(9) 0.2878(2) 0.30503(12) 0.0212(3) Uani 1 1 d . . . C4 C 0.45317(9) 0.3703(2) 0.38831(11) 0.0263(4) Uani 1 1 d . . . H4 H 0.4958 0.4258 0.4048 0.034(5) Uiso 1 1 calc R . . C5 C 0.40060(9) 0.3709(2) 0.44700(11) 0.0260(4) Uani 1 1 d . . . H5 H 0.4074 0.4317 0.5028 0.036(5) Uiso 1 1 calc R . . C6 C 0.26303(8) 0.1065(2) 0.33467(10) 0.0205(3) Uani 1 1 d . . . C7 C 0.61484(9) 0.2596(2) 0.20178(13) 0.0287(4) Uani 1 1 d . . . H7 H 0.6612 0.2319 0.2205 0.017(4) Uiso 1 1 calc R . . C8 C 0.56531(9) 0.2556(2) 0.26554(12) 0.0263(4) Uani 1 1 d . . . H8 H 0.5780 0.2289 0.3270 0.027(5) Uiso 1 1 calc R . . C9 C 0.49718(9) 0.2910(2) 0.23859(12) 0.0225(4) Uani 1 1 d . . . C10 C 0.48065(10) 0.3303(2) 0.14833(12) 0.0269(4) Uani 1 1 d . . . H10 H 0.4345 0.3537 0.1271 0.021(4) Uiso 1 1 calc R . . C11 C 0.53415(10) 0.3344(2) 0.08982(12) 0.0295(4) Uani 1 1 d . . . H11 H 0.5231 0.3630 0.0282 0.034(5) Uiso 1 1 calc R . . N1 N 0.34055(7) 0.28918(16) 0.42834(9) 0.0207(3) Uani 1 1 d . . . N2 N 0.59970(8) 0.30077(18) 0.11513(11) 0.0299(4) Uani 1 1 d . . . O1 O 0.22240(6) 0.12110(15) 0.39829(7) 0.0231(3) Uani 1 1 d . . . O2 O 0.25236(6) 0.01996(14) 0.26484(8) 0.0252(3) Uani 1 1 d . . . O3 O 0.20747(7) 0.49714(16) 0.41024(8) 0.0294(3) Uani 1 1 d D . . H3A H 0.2019(13) 0.5953(14) 0.4267(15) 0.056(7) Uiso 1 1 d D . . H3B H 0.2183(10) 0.504(3) 0.3597(7) 0.037(6) Uiso 1 1 d D . . O4 O 0.16108(7) 0.81259(16) 0.45079(10) 0.0300(3) Uani 1 1 d D . . H4A H 0.1822(10) 0.8968(18) 0.4413(14) 0.040(6) Uiso 1 1 d D . . H4B H 0.1529(13) 0.824(3) 0.5020(7) 0.046(7) 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 Zn1 0.02345(17) 0.02151(16) 0.01517(16) 0.000 0.00524(11) 0.000 C1 0.0216(9) 0.0196(8) 0.0182(8) 0.0016(6) 0.0012(6) 0.0036(6) C2 0.0231(9) 0.0217(8) 0.0168(8) 0.0002(6) 0.0022(6) 0.0026(6) C3 0.0230(9) 0.0207(8) 0.0203(9) 0.0033(6) 0.0033(7) 0.0016(6) C4 0.0240(9) 0.0299(9) 0.0248(9) -0.0012(7) 0.0016(7) -0.0047(7) C5 0.0277(9) 0.0303(9) 0.0201(9) -0.0037(7) 0.0008(7) -0.0026(7) C6 0.0236(8) 0.0192(8) 0.0188(8) 0.0023(6) 0.0020(6) 0.0017(6) C7 0.0237(9) 0.0267(9) 0.0363(11) -0.0036(8) 0.0054(8) -0.0036(7) C8 0.0253(9) 0.0262(8) 0.0274(10) -0.0001(7) 0.0027(7) -0.0032(7) C9 0.0247(9) 0.0189(8) 0.0244(9) -0.0011(6) 0.0051(7) -0.0021(6) C10 0.0280(10) 0.0277(9) 0.0252(9) -0.0002(7) 0.0026(7) 0.0010(7) C11 0.0372(11) 0.0285(9) 0.0234(10) 0.0013(7) 0.0077(8) -0.0019(7) N1 0.0237(8) 0.0220(7) 0.0166(7) 0.0005(5) 0.0022(6) 0.0005(5) N2 0.0307(9) 0.0266(8) 0.0336(9) -0.0040(6) 0.0116(7) -0.0042(6) O1 0.0252(6) 0.0250(6) 0.0199(6) -0.0029(5) 0.0083(5) -0.0030(5) O2 0.0263(6) 0.0292(6) 0.0204(6) -0.0050(5) 0.0035(5) -0.0032(5) O3 0.0456(8) 0.0261(7) 0.0172(7) 0.0030(5) 0.0080(6) 0.0088(6) O4 0.0376(8) 0.0256(7) 0.0280(8) -0.0020(5) 0.0112(6) -0.0048(5) _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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 6.8686 (0.0121) x - 6.4173 (0.0030) y + 5.7720 (0.0090) z = 2.9618 (0.0063) * -0.0060 (0.0010) N1 * 0.0158 (0.0010) C1 * -0.0092 (0.0011) C2 * -0.0063 (0.0011) C3 * 0.0158 (0.0012) C4 * -0.0100 (0.0012) C5 Rms deviation of fitted atoms = 0.0112 - 1.3282 (0.0093) x + 7.2239 (0.0023) y + 4.7859 (0.0138) z = 2.2300 (0.0068) Angle to previous plane (with approximate esd) = 46.72 ( 0.05 ) * -0.3028 (0.0011) N2 * -0.2085 (0.0005) C6 * -0.2060 (0.0014) C7 * 0.1364 (0.0013) C8 * 0.3534 (0.0014) C9 * 0.2276 (0.0011) C10 Rms deviation of fitted atoms = 0.2493 6.8686 (0.0121) x - 6.4173 (0.0030) y + 5.7720 (0.0090) z = 2.9618 (0.0063) Angle to previous plane (with approximate esd) = 46.72 ( 0.05 ) * -0.0060 (0.0010) N1 * 0.0158 (0.0010) C1 * -0.0092 (0.0011) C2 * -0.0063 (0.0011) C3 * 0.0158 (0.0012) C4 * -0.0100 (0.0012) C5 Rms deviation of fitted atoms = 0.0112 6.8686 (0.0121) x + 6.4173 (0.0031) y + 5.7720 (0.0090) z = 6.2445 (0.0052) Angle to previous plane (with approximate esd) = 65.82 ( 0.04 ) * 0.0060 (0.0010) N1_$4 * -0.0158 (0.0010) C1_$4 * 0.0092 (0.0011) C2_$4 * 0.0063 (0.0011) C3_$4 * -0.0158 (0.0012) C4_$4 * 0.0100 (0.0012) C5_$4 Rms deviation of fitted atoms = 0.0112 ; 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 Zn1 O1 2.1086(11) . ? Zn1 O1 2.1086(11) 2_556 ? Zn1 O3 2.1099(12) 2_556 ? Zn1 O3 2.1099(12) . ? Zn1 N1 2.1155(14) 2_556 ? Zn1 N1 2.1155(14) . ? C1 N1 1.343(2) . ? C1 C2 1.385(2) . ? C1 C6 1.524(2) . ? C2 C3 1.393(2) . ? C2 H2 0.9500 . ? C3 C4 1.388(2) . ? C3 C9 1.488(2) . ? C4 C5 1.382(2) . ? C4 H4 0.9500 . ? C5 N1 1.338(2) . ? C5 H5 0.9500 . ? C6 O2 1.2337(19) . ? C6 O1 1.2716(19) . ? C7 N2 1.336(2) . ? C7 C8 1.390(2) . ? C7 H7 0.9500 . ? C8 C9 1.386(3) . ? C8 H8 0.9500 . ? C9 C10 1.388(2) . ? C10 C11 1.395(2) . ? C10 H10 0.9500 . ? C11 N2 1.331(3) . ? C11 H11 0.9500 . ? O3 H3A 0.799(8) . ? O3 H3B 0.792(8) . ? O4 H4A 0.781(8) . ? O4 H4B 0.789(8) . ? 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 Zn1 O1 95.96(6) . 2_556 ? O1 Zn1 O3 170.40(4) . 2_556 ? O1 Zn1 O3 86.69(5) 2_556 2_556 ? O1 Zn1 O3 86.69(5) . . ? O1 Zn1 O3 170.40(4) 2_556 . ? O3 Zn1 O3 92.21(7) 2_556 . ? O1 Zn1 N1 97.77(5) . 2_556 ? O1 Zn1 N1 77.56(5) 2_556 2_556 ? O3 Zn1 N1 91.81(5) 2_556 2_556 ? O3 Zn1 N1 92.95(5) . 2_556 ? O1 Zn1 N1 77.56(5) . . ? O1 Zn1 N1 97.77(5) 2_556 . ? O3 Zn1 N1 92.95(5) 2_556 . ? O3 Zn1 N1 91.81(5) . . ? N1 Zn1 N1 173.13(7) 2_556 . ? N1 C1 C2 122.39(15) . . ? N1 C1 C6 115.45(13) . . ? C2 C1 C6 122.15(14) . . ? C1 C2 C3 119.07(15) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 118.21(15) . . ? C4 C3 C9 120.71(15) . . ? C2 C3 C9 121.08(15) . . ? C5 C4 C3 119.21(16) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? N1 C5 C4 122.63(16) . . ? N1 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? O2 C6 O1 126.01(15) . . ? O2 C6 C1 118.67(14) . . ? O1 C6 C1 115.32(14) . . ? N2 C7 C8 122.45(17) . . ? N2 C7 H7 118.8 . . ? C8 C7 H7 118.8 . . ? C9 C8 C7 119.38(17) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 118.63(16) . . ? C8 C9 C3 120.79(16) . . ? C10 C9 C3 120.58(16) . . ? C9 C10 C11 117.77(17) . . ? C9 C10 H10 121.1 . . ? C11 C10 H10 121.1 . . ? N2 C11 C10 123.99(17) . . ? N2 C11 H11 118.0 . . ? C10 C11 H11 118.0 . . ? C5 N1 C1 118.41(14) . . ? C5 N1 Zn1 127.71(11) . . ? C1 N1 Zn1 113.21(11) . . ? C11 N2 C7 117.76(15) . . ? C6 O1 Zn1 116.45(10) . . ? Zn1 O3 H3A 120.9(18) . . ? Zn1 O3 H3B 121.5(15) . . ? H3A O3 H3B 106(2) . . ? H4A O4 H4B 103(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 2.5(2) . . . . ? C6 C1 C2 C3 -176.49(14) . . . . ? C1 C2 C3 C4 -0.3(2) . . . . ? C1 C2 C3 C9 -179.80(14) . . . . ? C2 C3 C4 C5 -2.1(2) . . . . ? C9 C3 C4 C5 177.43(15) . . . . ? C3 C4 C5 N1 2.5(3) . . . . ? N1 C1 C6 O2 -177.06(14) . . . . ? C2 C1 C6 O2 2.0(2) . . . . ? N1 C1 C6 O1 2.0(2) . . . . ? C2 C1 C6 O1 -178.95(14) . . . . ? N2 C7 C8 C9 1.8(3) . . . . ? C7 C8 C9 C10 -0.3(2) . . . . ? C7 C8 C9 C3 179.98(15) . . . . ? C4 C3 C9 C8 46.2(2) . . . . ? C2 C3 C9 C8 -134.25(17) . . . . ? C4 C3 C9 C10 -133.43(18) . . . . ? C2 C3 C9 C10 46.1(2) . . . . ? C8 C9 C10 C11 -0.9(2) . . . . ? C3 C9 C10 C11 178.78(14) . . . . ? C9 C10 C11 N2 0.9(3) . . . . ? C4 C5 N1 C1 -0.4(2) . . . . ? C4 C5 N1 Zn1 -170.40(13) . . . . ? C2 C1 N1 C5 -2.1(2) . . . . ? C6 C1 N1 C5 176.90(14) . . . . ? C2 C1 N1 Zn1 169.27(12) . . . . ? C6 C1 N1 Zn1 -11.70(16) . . . . ? O1 Zn1 N1 C5 -177.27(15) . . . . ? O1 Zn1 N1 C5 -82.84(14) 2_556 . . . ? O3 Zn1 N1 C5 4.21(14) 2_556 . . . ? O3 Zn1 N1 C5 96.53(14) . . . . ? O1 Zn1 N1 C1 12.31(10) . . . . ? O1 Zn1 N1 C1 106.73(11) 2_556 . . . ? O3 Zn1 N1 C1 -166.21(11) 2_556 . . . ? O3 Zn1 N1 C1 -73.90(11) . . . . ? C10 C11 N2 C7 0.4(3) . . . . ? C8 C7 N2 C11 -1.8(3) . . . . ? O2 C6 O1 Zn1 -171.98(12) . . . . ? C1 C6 O1 Zn1 9.01(17) . . . . ? O1 Zn1 O1 C6 -108.43(12) 2_556 . . . ? O3 Zn1 O1 C6 80.83(12) . . . . ? N1 Zn1 O1 C6 173.36(11) 2_556 . . . ? N1 Zn1 O1 C6 -11.76(11) . . . . ? 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 H3A O4 0.799(8) 1.884(11) 2.6562(17) 162(3) . O3 H3B O2 0.792(8) 1.971(9) 2.7564(17) 171(2) 7 O4 H4A O1 0.781(8) 2.004(9) 2.7753(17) 169(2) 1_565 O4 H4B N2 0.789(8) 2.031(12) 2.777(2) 158(2) 3_455 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.456 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.064 # Attachment '5.cif' data_je1095ms _database_code_depnum_ccdc_archive 'CCDC 601017' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H14 Cu Hg I2 N4 O4' _chemical_formula_sum 'C22 H14 Cu Hg I2 N4 O4' _chemical_formula_weight 916.30 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Hg Hg -2.3894 9.2266 '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 30.3812(18) _cell_length_b 5.0478(3) _cell_length_c 16.3401(9) _cell_angle_alpha 90.00 _cell_angle_beta 108.2680(10) _cell_angle_gamma 90.00 _cell_volume 2379.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 4397 _cell_measurement_theta_min 2.562 _cell_measurement_theta_max 26.316 _exptl_crystal_description bar _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.558 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1684 _exptl_absorpt_coefficient_mu 9.970 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6390 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details '(SADABS, Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 12484 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0261 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 26.39 _reflns_number_total 2444 _reflns_number_gt 2223 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0354P)^2^+24.9787P] 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_number_reflns 2444 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0806 _refine_ls_wR_factor_gt 0.0782 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 Hg1 Hg 0.0000 0.93486(7) 0.2500 0.02627(11) Uani 1 2 d S . . I1 I 0.053152(16) 1.09397(10) 0.40414(3) 0.03898(14) Uani 1 1 d . . . Cu1 Cu 0.2500 -0.2500 0.0000 0.0258(2) Uani 1 2 d S . . C1 C 0.1867(2) 0.1165(12) 0.0196(4) 0.0233(12) Uani 1 1 d . . . C2 C 0.1556(2) 0.2542(12) 0.0476(4) 0.0238(12) Uani 1 1 d . . . H2 H 0.1392 0.3993 0.0149 0.029 Uiso 1 1 calc R . . C3 C 0.1477(2) 0.1822(13) 0.1242(4) 0.0255(12) Uani 1 1 d . . . C4 C 0.1732(2) -0.0307(13) 0.1699(4) 0.0277(13) Uani 1 1 d . . . H4 H 0.1698 -0.0833 0.2234 0.033 Uiso 1 1 calc R . . C5 C 0.2036(2) -0.1648(13) 0.1364(4) 0.0282(13) Uani 1 1 d . . . H5 H 0.2206 -0.3106 0.1675 0.034 Uiso 1 1 calc R . . C6 C 0.1993(2) 0.1959(13) -0.0596(4) 0.0275(13) Uani 1 1 d . . . C7 C 0.0447(2) 0.5943(14) 0.1236(4) 0.0343(15) Uani 1 1 d . . . H7 H 0.0178 0.6655 0.0825 0.041 Uiso 1 1 calc R . . C8 C 0.0743(2) 0.4403(14) 0.0947(4) 0.0329(15) Uani 1 1 d . . . H8 H 0.0679 0.4082 0.0348 0.039 Uiso 1 1 calc R . . C9 C 0.1140(2) 0.3312(13) 0.1545(4) 0.0257(12) Uani 1 1 d . . . C10 C 0.1211(2) 0.3823(13) 0.2412(4) 0.0294(14) Uani 1 1 d . . . H10 H 0.1470 0.3083 0.2840 0.035 Uiso 1 1 calc R . . C11 C 0.0899(2) 0.5430(13) 0.2643(4) 0.0288(13) Uani 1 1 d . . . H11 H 0.0955 0.5804 0.3237 0.035 Uiso 1 1 calc R . . N1 N 0.20974(17) -0.0957(9) 0.0617(3) 0.0228(10) Uani 1 1 d . . . N2 N 0.05232(17) 0.6476(11) 0.2073(3) 0.0271(11) Uani 1 1 d . . . O1 O 0.22538(15) 0.0285(9) -0.0829(3) 0.0272(9) Uani 1 1 d . . . O2 O 0.18639(15) 0.4096(9) -0.0933(3) 0.0326(10) Uani 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 Hg1 0.02558(18) 0.0295(2) 0.02719(18) 0.000 0.01328(13) 0.000 I1 0.0436(3) 0.0381(3) 0.0351(3) -0.00182(19) 0.0121(2) -0.00431(19) Cu1 0.0286(5) 0.0234(5) 0.0304(5) 0.0027(4) 0.0165(4) 0.0059(4) C1 0.020(3) 0.024(3) 0.026(3) 0.000(2) 0.008(2) -0.003(2) C2 0.024(3) 0.022(3) 0.028(3) 0.000(2) 0.012(2) 0.000(2) C3 0.022(3) 0.026(3) 0.029(3) -0.007(3) 0.009(2) -0.001(2) C4 0.032(3) 0.026(3) 0.028(3) -0.002(3) 0.014(3) -0.003(3) C5 0.031(3) 0.028(3) 0.031(3) 0.001(3) 0.016(3) 0.001(3) C6 0.025(3) 0.027(3) 0.031(3) -0.001(3) 0.010(3) 0.000(3) C7 0.032(3) 0.042(4) 0.029(3) -0.005(3) 0.010(3) 0.003(3) C8 0.024(3) 0.047(4) 0.028(3) -0.009(3) 0.007(3) 0.006(3) C9 0.023(3) 0.027(3) 0.028(3) -0.004(3) 0.010(2) -0.006(2) C10 0.030(3) 0.032(4) 0.028(3) 0.000(3) 0.012(3) 0.003(3) C11 0.029(3) 0.033(3) 0.026(3) -0.004(3) 0.011(3) 0.001(3) N1 0.021(2) 0.020(3) 0.029(3) 0.001(2) 0.011(2) 0.0011(19) N2 0.024(3) 0.032(3) 0.030(3) 0.001(2) 0.015(2) 0.001(2) O1 0.032(2) 0.027(2) 0.026(2) 0.0019(18) 0.0142(18) 0.0064(19) O2 0.027(2) 0.033(3) 0.039(3) 0.011(2) 0.013(2) 0.0108(19) _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 Hg1 N2 2.411(5) . ? Hg1 N2 2.411(5) 2 ? Hg1 I1 2.6545(5) 2 ? Hg1 I1 2.6545(5) . ? Cu1 O1 1.933(4) . ? Cu1 O1 1.933(4) 7_545 ? Cu1 N1 1.972(5) 7_545 ? Cu1 N1 1.972(5) . ? Cu1 O2 2.677(5) 7 ? Cu1 O2 2.677(5) 1_545 ? C1 N1 1.344(8) . ? C1 C2 1.363(8) . ? C1 C6 1.513(8) . ? C2 C3 1.393(8) . ? C2 H2 0.9500 . ? C3 C4 1.396(9) . ? C3 C9 1.476(8) . ? C4 C5 1.389(9) . ? C4 H4 0.9500 . ? C5 N1 1.338(8) . ? C5 H5 0.9500 . ? C6 O2 1.219(8) . ? C6 O1 1.295(7) . ? C7 N2 1.340(8) . ? C7 C8 1.380(9) . ? C7 H7 0.9500 . ? C8 C9 1.404(9) . ? C8 H8 0.9500 . ? C9 C10 1.389(9) . ? C10 C11 1.388(9) . ? C10 H10 0.9500 . ? C11 N2 1.335(8) . ? C11 H11 0.9500 . ? 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 Hg1 N2 106.1(3) . 2 ? N2 Hg1 I1 99.64(12) . 2 ? N2 Hg1 I1 101.33(13) 2 2 ? N2 Hg1 I1 101.34(13) . . ? N2 Hg1 I1 99.64(12) 2 . ? I1 Hg1 I1 144.78(3) 2 . ? O1 Cu1 O1 180.0 . 7_545 ? O1 Cu1 N1 95.43(19) . 7_545 ? O1 Cu1 N1 84.57(19) 7_545 7_545 ? O1 Cu1 N1 84.57(19) . . ? O1 Cu1 N1 95.43(19) 7_545 . ? N1 Cu1 N1 179.998(1) 7_545 . ? O1 Cu1 O2 89.09(16) . 7 ? O1 Cu1 O2 90.91(16) 7_545 7 ? N1 Cu1 O2 95.28(17) 7_545 7 ? N1 Cu1 O2 84.73(17) . 7 ? O1 Cu1 O2 90.91(16) . 1_545 ? O1 Cu1 O2 89.09(16) 7_545 1_545 ? N1 Cu1 O2 84.72(17) 7_545 1_545 ? N1 Cu1 O2 95.27(17) . 1_545 ? O2 Cu1 O2 180.0(3) 7 1_545 ? N1 C1 C2 122.6(5) . . ? N1 C1 C6 114.7(5) . . ? C2 C1 C6 122.6(5) . . ? C1 C2 C3 120.0(6) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C2 C3 C4 117.4(5) . . ? C2 C3 C9 120.0(6) . . ? C4 C3 C9 122.6(6) . . ? C5 C4 C3 119.3(6) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? N1 C5 C4 122.3(6) . . ? N1 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? O2 C6 O1 125.7(6) . . ? O2 C6 C1 119.3(6) . . ? O1 C6 C1 114.9(5) . . ? N2 C7 C8 122.6(6) . . ? N2 C7 H7 118.7 . . ? C8 C7 H7 118.7 . . ? C7 C8 C9 119.6(6) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 117.5(6) . . ? C10 C9 C3 122.3(6) . . ? C8 C9 C3 120.1(5) . . ? C11 C10 C9 119.0(6) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? N2 C11 C10 123.3(6) . . ? N2 C11 H11 118.4 . . ? C10 C11 H11 118.4 . . ? C5 N1 C1 118.3(5) . . ? C5 N1 Cu1 130.5(4) . . ? C1 N1 Cu1 111.1(4) . . ? C11 N2 C7 118.0(6) . . ? C11 N2 Hg1 122.2(4) . . ? C7 N2 Hg1 119.8(4) . . ? C6 O1 Cu1 113.9(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 2.3(9) . . . . ? C6 C1 C2 C3 -175.7(6) . . . . ? C1 C2 C3 C4 0.7(9) . . . . ? C1 C2 C3 C9 -180.0(6) . . . . ? C2 C3 C4 C5 -2.1(9) . . . . ? C9 C3 C4 C5 178.6(6) . . . . ? C3 C4 C5 N1 0.6(10) . . . . ? N1 C1 C6 O2 -167.6(6) . . . . ? C2 C1 C6 O2 10.5(9) . . . . ? N1 C1 C6 O1 9.2(8) . . . . ? C2 C1 C6 O1 -172.7(6) . . . . ? N2 C7 C8 C9 0.6(11) . . . . ? C7 C8 C9 C10 0.8(10) . . . . ? C7 C8 C9 C3 -175.6(6) . . . . ? C2 C3 C9 C10 -143.0(6) . . . . ? C4 C3 C9 C10 36.2(9) . . . . ? C2 C3 C9 C8 33.3(9) . . . . ? C4 C3 C9 C8 -147.5(6) . . . . ? C8 C9 C10 C11 -1.9(10) . . . . ? C3 C9 C10 C11 174.5(6) . . . . ? C9 C10 C11 N2 1.6(10) . . . . ? C4 C5 N1 C1 2.3(9) . . . . ? C4 C5 N1 Cu1 -179.9(5) . . . . ? C2 C1 N1 C5 -3.7(8) . . . . ? C6 C1 N1 C5 174.4(5) . . . . ? C2 C1 N1 Cu1 178.0(5) . . . . ? C6 C1 N1 Cu1 -3.9(6) . . . . ? O1 Cu1 N1 C5 -178.8(6) . . . . ? O1 Cu1 N1 C5 1.2(6) 7_545 . . . ? O2 Cu1 N1 C5 -89.2(5) 7 . . . ? O2 Cu1 N1 C5 90.8(5) 1_545 . . . ? O1 Cu1 N1 C1 -0.8(4) . . . . ? O1 Cu1 N1 C1 179.1(4) 7_545 . . . ? O2 Cu1 N1 C1 88.7(4) 7 . . . ? O2 Cu1 N1 C1 -91.3(4) 1_545 . . . ? C10 C11 N2 C7 -0.2(10) . . . . ? C10 C11 N2 Hg1 -178.4(5) . . . . ? C8 C7 N2 C11 -1.0(10) . . . . ? C8 C7 N2 Hg1 177.3(5) . . . . ? N2 Hg1 N2 C11 -83.6(5) 2 . . . ? I1 Hg1 N2 C11 171.5(5) 2 . . . ? I1 Hg1 N2 C11 20.0(5) . . . . ? N2 Hg1 N2 C7 98.2(5) 2 . . . ? I1 Hg1 N2 C7 -6.7(5) 2 . . . ? I1 Hg1 N2 C7 -158.2(5) . . . . ? O2 C6 O1 Cu1 166.9(5) . . . . ? C1 C6 O1 Cu1 -9.8(6) . . . . ? N1 Cu1 O1 C6 -173.8(4) 7_545 . . . ? N1 Cu1 O1 C6 6.2(4) . . . . ? O2 Cu1 O1 C6 -78.6(4) 7 . . . ? O2 Cu1 O1 C6 101.4(4) 1_545 . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.949 _refine_diff_density_min -1.014 _refine_diff_density_rms 0.160