# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _chemical_name_systematic ? _chemical_name_common '[Mn2(tpa)2(adc)2].6H2O' _chemical_formula_moiety 'C44 H36 N8 Mn2 O8, 6 (H2 O)' _chemical_formula_sum 'C44 H48 Mn2 N8 O14' _chemical_formula_iupac ? _chemical_formula_weight 1022.78 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_operation_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 19.8422(6) _cell_length_b 13.8805(4) _cell_length_c 17.2350(5) _cell_angle_alpha 90 _cell_angle_beta 101.4770(10) _cell_angle_gamma 90 _cell_volume 4651.9(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 432 _cell_measurement_theta_min 3.1707 _cell_measurement_theta_max 28.4981 _cell_measurement_temperature 100.(2) _exptl_crystal_description 'block shaped' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.300 _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2120 _exptl_absorpt_coefficient_mu 0.618 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.6935 _exptl_absorpt_correction_T_max 0.7452 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_source 'sealed tube' _diffrn_source_type 'fine focus' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEX II' _diffrn_measurement_method 'phi and Omega scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 29607 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0122 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.17 _diffrn_reflns_theta_full 25.17 _diffrn_measured_fraction_theta_max 0.971 _diffrn_measured_fraction_theta_full 0.971 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _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. ; _reflns_number_total 4060 _reflns_number_gt 3725 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_gt 0.0680 _refine_ls_wR_factor_ref 0.0710 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_number_reflns 4060 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+9.1631P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.402 _refine_diff_density_min -0.225 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' _computing_data_collection 'APEX2 V2011.4-1 (Bruker AXS)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Bruker AXS)' _computing_publication_material 'SHELXTL (Bruker AXS)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Mn Mn1 0.276152(12) 0.534644(17) 0.145436(14) 0.01781(9) Uani d . 1 . . N N4 0.36311(7) 0.61384(10) 0.23077(8) 0.0222(3) Uani d . 1 . . N N2 0.33644(7) 0.41813(10) 0.22938(8) 0.0183(3) Uani d . 1 . . N N1 0.21228(7) 0.51474(9) 0.23740(8) 0.0193(3) Uani d . 1 . . N N3 0.22842(7) 0.38821(10) 0.10056(8) 0.0201(3) Uani d . 1 . . O O2 0.23791(7) 0.67706(9) 0.11614(8) 0.0334(3) Uani d . 1 . . O O1 0.34553(6) 0.50899(8) 0.06839(7) 0.0249(3) Uani d . 1 . . O O3 0.15866(9) 0.59994(10) 0.02993(8) 0.0452(4) Uani d . 1 . . O O4 0.41295(6) 0.51803(8) -0.01936(7) 0.0268(3) Uani d . 1 . . O O5 0.48669(7) 0.36873(9) 0.07021(8) 0.0301(3) Uani d . 1 . . H H5A 0.5232(13) 0.3921(17) 0.0563(13) 0.045 Uiso d . 1 . . H H5B 0.4543(12) 0.4033(18) 0.0472(14) 0.045 Uiso d . 1 . . O O6 0.48076(11) 0.91667(17) 0.95739(16) 0.0956(8) Uani d . 1 . . O O7 0.01312(8) 0.71028(11) 0.17062(9) 0.0395(3) Uani d . 1 . . H H7B 0.0107(13) 0.667(2) 0.1272(15) 0.059 Uiso d . 1 . . H H7C 0.0013(13) 0.761(2) 0.1410(16) 0.059 Uiso d . 1 . . C C1 0.41098(8) 0.55797(12) 0.27507(9) 0.0208(3) Uani d . 1 . . C C2 0.40823(8) 0.45248(12) 0.25328(10) 0.0204(3) Uani d . 1 . . H H2A 0.4326 0.4423 0.2091 0.025 Uiso calc R 1 . . H H2B 0.4321 0.4144 0.2992 0.025 Uiso calc R 1 . . C C3 0.30512(8) 0.40578(12) 0.29990(9) 0.0219(4) Uani d . 1 . . H H3A 0.337 0.433 0.3463 0.026 Uiso calc R 1 . . H H3B 0.301 0.3359 0.3096 0.026 Uiso calc R 1 . . C C4 0.23519(8) 0.45143(11) 0.29543(9) 0.0190(3) Uani d . 1 . . C C5 0.15058(9) 0.55636(12) 0.23499(10) 0.0231(4) Uani d . 1 . . H H5 0.134 0.6005 0.1934 0.028 Uiso calc R 1 . . C C6 0.11048(9) 0.53803(13) 0.28984(11) 0.0271(4) Uani d . 1 . . H H6 0.0673 0.569 0.2864 0.033 Uiso calc R 1 . . C C7 0.13453(9) 0.47326(13) 0.35046(10) 0.0277(4) Uani d . 1 . . H H7 0.1082 0.4592 0.3894 0.033 Uiso calc R 1 . . C C8 0.19756(9) 0.42956(12) 0.35303(10) 0.0238(4) Uani d . 1 . . H H8 0.215 0.3849 0.3939 0.029 Uiso calc R 1 . . C C9 0.33426(8) 0.32854(11) 0.18235(10) 0.0215(3) Uani d . 1 . . H H9A 0.3465 0.2734 0.2188 0.026 Uiso calc R 1 . . H H9B 0.3691 0.3327 0.1485 0.026 Uiso calc R 1 . . C C10 0.26470(8) 0.31033(12) 0.13067(9) 0.0202(3) Uani d . 1 . . C C11 0.16822(9) 0.37388(12) 0.05020(9) 0.0228(4) Uani d . 1 . . H H11 0.1419 0.4286 0.0293 0.027 Uiso calc R 1 . . C C12 0.14278(9) 0.28349(13) 0.02740(10) 0.0268(4) Uani d . 1 . . H H12 0.1002 0.2763 -0.0087 0.032 Uiso calc R 1 . . C C13 0.18043(9) 0.20350(13) 0.05802(10) 0.0282(4) Uani d . 1 . . H H13 0.1644 0.1404 0.043 0.034 Uiso calc R 1 . . C C14 0.24192(9) 0.21717(12) 0.11090(10) 0.0243(4) Uani d . 1 . . H H14 0.2683 0.1634 0.1335 0.029 Uiso calc R 1 . . C C15 0.46249(9) 0.59538(13) 0.33398(10) 0.0251(4) Uani d . 1 . . H H15 0.4945 0.5538 0.366 0.03 Uiso calc R 1 . . C C16 0.46643(10) 0.69420(14) 0.34538(11) 0.0297(4) Uani d . 1 . . H H16 0.5015 0.7215 0.3849 0.036 Uiso calc R 1 . . C C17 0.41845(10) 0.75227(13) 0.29826(11) 0.0305(4) Uani d . 1 . . H H17 0.4206 0.8203 0.3039 0.037 Uiso calc R 1 . . C C18 0.36738(9) 0.70961(12) 0.24281(11) 0.0271(4) Uani d . 1 . . H H18 0.3337 0.7497 0.2117 0.032 Uiso calc R 1 . . C C19 0.18869(10) 0.67325(12) 0.05851(10) 0.0254(4) Uani d . 1 . . C C20 0.16464(9) 0.76696(12) 0.02338(9) 0.0225(4) Uani d . 1 . . C C21 0.35234(8) 0.65404(12) 0.00075(9) 0.0210(3) Uani d . 1 . . C C22 0.37155(8) 0.55294(12) 0.01894(9) 0.0191(3) Uani d . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Mn1 0.02021(14) 0.01486(14) 0.01759(13) 0.00130(9) 0.00191(10) 0.00201(9) N4 0.0253(8) 0.0179(7) 0.0232(7) -0.0001(6) 0.0045(6) 0.0013(6) N2 0.0184(7) 0.0168(7) 0.0190(7) 0.0000(5) 0.0023(5) 0.0006(5) N1 0.0213(7) 0.0169(7) 0.0187(7) 0.0008(6) 0.0014(5) -0.0010(5) N3 0.0230(7) 0.0182(7) 0.0189(7) 0.0004(6) 0.0033(6) 0.0001(5) O2 0.0328(7) 0.0307(7) 0.0361(7) 0.0105(6) 0.0054(6) 0.0136(6) O1 0.0301(7) 0.0204(6) 0.0254(6) 0.0031(5) 0.0087(5) 0.0037(5) O3 0.0829(12) 0.0206(7) 0.0336(7) -0.0030(7) 0.0148(7) -0.0015(6) O4 0.0299(7) 0.0233(6) 0.0293(6) 0.0061(5) 0.0109(5) 0.0048(5) O5 0.0282(7) 0.0265(7) 0.0337(7) 0.0009(6) 0.0015(6) 0.0086(5) O6 0.0602(13) 0.0853(15) 0.136(2) -0.0023(11) 0.0064(13) -0.0648(15) O7 0.0500(9) 0.0285(8) 0.0398(8) 0.0023(7) 0.0084(7) 0.0046(6) C1 0.0202(8) 0.0218(8) 0.0212(8) -0.0008(7) 0.0056(7) 0.0020(7) C2 0.0179(8) 0.0198(8) 0.0225(8) 0.0011(6) 0.0012(7) 0.0020(6) C3 0.0236(9) 0.0217(9) 0.0198(8) 0.0012(7) 0.0030(7) 0.0049(6) C4 0.0224(9) 0.0156(8) 0.0177(8) -0.0019(6) 0.0005(6) -0.0026(6) C5 0.0257(9) 0.0199(8) 0.0223(8) 0.0035(7) 0.0011(7) -0.0002(7) C6 0.0241(9) 0.0284(10) 0.0290(9) 0.0047(7) 0.0059(7) -0.0015(7) C7 0.0280(10) 0.0309(10) 0.0259(9) 0.0003(8) 0.0099(7) 0.0004(7) C8 0.0276(9) 0.0214(9) 0.0218(8) -0.0005(7) 0.0033(7) 0.0024(7) C9 0.0227(9) 0.0156(8) 0.0251(8) 0.0022(7) 0.0019(7) 0.0010(6) C10 0.0239(9) 0.0182(8) 0.0189(8) 0.0008(7) 0.0052(7) 0.0011(6) C11 0.0246(9) 0.0214(9) 0.0208(8) 0.0017(7) 0.0004(7) 0.0016(7) C12 0.0281(9) 0.0252(9) 0.0245(9) -0.0024(7) -0.0005(7) -0.0015(7) C13 0.0328(10) 0.0201(9) 0.0304(9) -0.0064(7) 0.0034(8) -0.0039(7) C14 0.0281(9) 0.0180(9) 0.0262(9) 0.0013(7) 0.0042(7) 0.0012(7) C15 0.0250(9) 0.0272(9) 0.0229(8) -0.0026(7) 0.0042(7) 0.0008(7) C16 0.0310(10) 0.0306(10) 0.0264(9) -0.0081(8) 0.0034(8) -0.0050(7) C17 0.0390(11) 0.0204(9) 0.0334(10) -0.0060(8) 0.0102(8) -0.0049(7) C18 0.0308(10) 0.0194(9) 0.0309(9) 0.0009(7) 0.0059(8) 0.0015(7) C19 0.0377(10) 0.0190(9) 0.0235(9) 0.0042(8) 0.0160(8) 0.0000(7) C20 0.0254(9) 0.0228(9) 0.0188(8) 0.0006(7) 0.0034(7) 0.0001(7) C21 0.0227(9) 0.0229(9) 0.0175(8) 0.0005(7) 0.0045(6) 0.0005(7) C22 0.0196(8) 0.0192(8) 0.0161(8) 0.0021(6) -0.0020(6) -0.0006(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. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Mn1 O1 . 2.1242(12) ? Mn1 O2 . 2.1415(13) ? Mn1 N1 . 2.2349(14) ? Mn1 N3 . 2.3097(13) ? Mn1 N4 . 2.3106(14) ? Mn1 N2 . 2.3346(13) ? N4 C1 . 1.341(2) ? N4 C18 . 1.346(2) ? N2 C9 . 1.480(2) ? N2 C2 . 1.481(2) ? N2 C3 . 1.481(2) ? N1 C4 . 1.341(2) ? N1 C5 . 1.347(2) ? N3 C11 . 1.344(2) ? N3 C10 . 1.344(2) ? O2 C19 . 1.248(2) ? O1 C22 . 1.241(2) ? O3 C19 . 1.232(2) ? O4 C22 . 1.249(2) ? O5 H5A . 0.87(2) ? O5 H5B . 0.84(3) ? O7 H7B . 0.96(3) ? O7 H7C . 0.88(3) ? C1 C15 . 1.390(2) ? C1 C2 . 1.510(2) ? C2 H2A . 0.99 ? C2 H2B . 0.99 ? C3 C4 . 1.513(2) ? C3 H3A . 0.99 ? C3 H3B . 0.99 ? C4 C8 . 1.389(2) ? C5 C6 . 1.375(3) ? C5 H5 . 0.95 ? C6 C7 . 1.389(3) ? C6 H6 . 0.95 ? C7 C8 . 1.383(3) ? C7 H7 . 0.95 ? C8 H8 . 0.95 ? C9 C10 . 1.508(2) ? C9 H9A . 0.99 ? C9 H9B . 0.99 ? C10 C14 . 1.390(2) ? C11 C12 . 1.380(2) ? C11 H11 . 0.95 ? C12 C13 . 1.383(3) ? C12 H12 . 0.95 ? C13 C14 . 1.383(3) ? C13 H13 . 0.95 ? C14 H14 . 0.95 ? C15 C16 . 1.386(3) ? C15 H15 . 0.95 ? C16 C17 . 1.381(3) ? C16 H16 . 0.95 ? C17 C18 . 1.380(3) ? C17 H17 . 0.95 ? C18 H18 . 0.95 ? C19 C20 . 1.474(2) ? C20 C21 7_565 1.197(2) ? C21 C20 7_565 1.197(2) ? C21 C22 . 1.471(2) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 Mn1 O2 . . 104.52(5) ? O1 Mn1 N1 . . 162.20(5) ? O2 Mn1 N1 . . 93.27(5) ? O1 Mn1 N3 . . 85.22(5) ? O2 Mn1 N3 . . 129.12(5) ? N1 Mn1 N3 . . 82.88(5) ? O1 Mn1 N4 . . 89.02(5) ? O2 Mn1 N4 . . 84.01(5) ? N1 Mn1 N4 . . 93.69(5) ? N3 Mn1 N4 . . 146.75(5) ? O1 Mn1 N2 . . 87.44(5) ? O2 Mn1 N2 . . 154.07(5) ? N1 Mn1 N2 . . 76.57(5) ? N3 Mn1 N2 . . 73.94(5) ? N4 Mn1 N2 . . 73.11(5) ? C1 N4 C18 . . 117.90(15) ? C1 N4 Mn1 . . 116.23(11) ? C18 N4 Mn1 . . 125.75(12) ? C9 N2 C2 . . 110.15(12) ? C9 N2 C3 . . 112.38(13) ? C2 N2 C3 . . 110.27(12) ? C9 N2 Mn1 . . 106.68(9) ? C2 N2 Mn1 . . 107.18(9) ? C3 N2 Mn1 . . 109.99(9) ? C4 N1 C5 . . 118.38(14) ? C4 N1 Mn1 . . 117.00(11) ? C5 N1 Mn1 . . 124.43(11) ? C11 N3 C10 . . 117.96(14) ? C11 N3 Mn1 . . 126.79(11) ? C10 N3 Mn1 . . 115.21(10) ? C19 O2 Mn1 . . 109.45(12) ? C22 O1 Mn1 . . 139.18(11) ? H5A O5 H5B . . 105.(2) ? H7B O7 H7C . . 95.(2) ? N4 C1 C15 . . 122.31(16) ? N4 C1 C2 . . 115.64(14) ? C15 C1 C2 . . 121.93(15) ? N2 C2 C1 . . 111.50(13) ? N2 C2 H2A . . 109.3 ? C1 C2 H2A . . 109.3 ? N2 C2 H2B . . 109.3 ? C1 C2 H2B . . 109.3 ? H2A C2 H2B . . 108.0 ? N2 C3 C4 . . 116.10(13) ? N2 C3 H3A . . 108.3 ? C4 C3 H3A . . 108.3 ? N2 C3 H3B . . 108.3 ? C4 C3 H3B . . 108.3 ? H3A C3 H3B . . 107.4 ? N1 C4 C8 . . 121.69(15) ? N1 C4 C3 . . 118.93(14) ? C8 C4 C3 . . 119.33(14) ? N1 C5 C6 . . 123.11(16) ? N1 C5 H5 . . 118.4 ? C6 C5 H5 . . 118.4 ? C5 C6 C7 . . 118.53(16) ? C5 C6 H6 . . 120.7 ? C7 C6 H6 . . 120.7 ? C8 C7 C6 . . 118.78(16) ? C8 C7 H7 . . 120.6 ? C6 C7 H7 . . 120.6 ? C7 C8 C4 . . 119.50(16) ? C7 C8 H8 . . 120.2 ? C4 C8 H8 . . 120.2 ? N2 C9 C10 . . 112.83(13) ? N2 C9 H9A . . 109.0 ? C10 C9 H9A . . 109.0 ? N2 C9 H9B . . 109.0 ? C10 C9 H9B . . 109.0 ? H9A C9 H9B . . 107.8 ? N3 C10 C14 . . 122.04(15) ? N3 C10 C9 . . 116.75(14) ? C14 C10 C9 . . 121.05(15) ? N3 C11 C12 . . 123.10(16) ? N3 C11 H11 . . 118.5 ? C12 C11 H11 . . 118.5 ? C11 C12 C13 . . 118.82(16) ? C11 C12 H12 . . 120.6 ? C13 C12 H12 . . 120.6 ? C14 C13 C12 . . 118.69(16) ? C14 C13 H13 . . 120.7 ? C12 C13 H13 . . 120.7 ? C13 C14 C10 . . 119.37(16) ? C13 C14 H14 . . 120.3 ? C10 C14 H14 . . 120.3 ? C16 C15 C1 . . 119.06(17) ? C16 C15 H15 . . 120.5 ? C1 C15 H15 . . 120.5 ? C17 C16 C15 . . 118.79(17) ? C17 C16 H16 . . 120.6 ? C15 C16 H16 . . 120.6 ? C18 C17 C16 . . 118.81(17) ? C18 C17 H17 . . 120.6 ? C16 C17 H17 . . 120.6 ? N4 C18 C17 . . 123.06(17) ? N4 C18 H18 . . 118.5 ? C17 C18 H18 . . 118.5 ? O3 C19 O2 . . 126.39(17) ? O3 C19 C20 . . 118.27(16) ? O2 C19 C20 . . 115.34(16) ? C21 C20 C19 7_565 . 175.60(18) ? C20 C21 C22 7_565 . 172.15(17) ? O1 C22 O4 . . 125.40(15) ? O1 C22 C21 . . 119.31(15) ? O4 C22 C21 . . 115.27(14) ? _database_code_depnum_ccdc_archive 'CCDC 932447' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _chemical_name_systematic ? _chemical_name_common '[Mn2(tpa)2(fumarate)2].8H2O' _chemical_formula_moiety 'C44 H40 N8 Mn2 O8, 8(H2O)' _chemical_formula_sum 'C44 H56 Mn2 N8 O16' _chemical_formula_iupac ? _chemical_formula_weight 1062.85 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_operation_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 20.877(5) _cell_length_b 14.366(3) _cell_length_c 16.576(4) _cell_angle_alpha 90 _cell_angle_beta 106.014(3) _cell_angle_gamma 90 _cell_volume 4778.5(19) _cell_formula_units_Z 4 _cell_measurement_reflns_used 107 _cell_measurement_theta_min 4.7163 _cell_measurement_theta_max 23.5979 _cell_measurement_temperature 100.(2) _exptl_crystal_description 'block shaped' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2216 _exptl_absorpt_coefficient_mu 0.608 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.69 _exptl_absorpt_correction_T_max 0.75 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_source 'sealed tube' _diffrn_source_type 'fine focus' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEX 2' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 16298 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _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. ; _reflns_number_total 4199 _reflns_number_gt 3037 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_gt 0.1072 _refine_ls_wR_factor_ref 0.1186 _refine_ls_goodness_of_fit_ref 1.173 _refine_ls_restrained_S_all 1.173 _refine_ls_number_reflns 4199 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.536 _refine_diff_density_min -0.560 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' _computing_data_collection 'APEX2 V2011.4-1 (Bruker AXS)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Bruker AXS)' _computing_publication_material 'SHELXTL (Bruker AXS)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Mn Mn1 0.24158(2) 0.46622(4) 0.38410(3) 0.01731(16) Uani d . 1 . . N N2 0.17183(13) 0.56645(19) 0.28578(15) 0.0217(7) Uani d . 1 . . N N4 0.16054(14) 0.37509(19) 0.29721(15) 0.0218(7) Uani d . 1 . . N N1 0.28883(13) 0.47105(19) 0.27786(14) 0.0203(6) Uani d . 1 . . N N3 0.28381(13) 0.61123(19) 0.41497(15) 0.0201(6) Uani d . 1 . . O O1 0.17508(11) 0.48324(15) 0.46029(12) 0.0220(5) Uani d . 1 . . O O4 0.07671(13) 0.44727(18) 0.47835(16) 0.0400(7) Uani d . 1 . . O O3 0.09949(12) 0.09614(17) 0.49903(13) 0.0286(6) Uani d . 1 . . O O5 0.01150(13) 0.61194(17) 0.43536(15) 0.0311(6) Uani d G 1 . . H H5A 0.0383 0.5644 0.4458 0.047 Uiso d G 1 . . H H5B -0.022 0.602 0.456 0.047 Uiso d G 1 . . C C1 0.10470(17) 0.5238(2) 0.26323(19) 0.0237(8) Uani d . 1 . . H H1A 0.0763 0.5546 0.2124 0.028 Uiso calc R 1 . . H H1B 0.0839 0.5335 0.3095 0.028 Uiso calc R 1 . . C C2 0.10835(17) 0.4210(2) 0.24685(18) 0.0214(8) Uani d . 1 . . C C3 0.05847(17) 0.3756(3) 0.18642(19) 0.0263(9) Uani d . 1 . . H H3 0.0228 0.4097 0.1507 0.032 Uiso calc R 1 . . C C4 0.06198(18) 0.2804(3) 0.1795(2) 0.0301(9) Uani d . 1 . . H H4 0.0283 0.2479 0.1391 0.036 Uiso calc R 1 . . C C5 0.11492(18) 0.2322(2) 0.23175(19) 0.0262(8) Uani d . 1 . . H H5 0.1178 0.1664 0.2282 0.031 Uiso calc R 1 . . C C6 0.16312(17) 0.2817(2) 0.28877(18) 0.0223(8) Uani d . 1 . . H H6 0.1999 0.2488 0.3238 0.027 Uiso calc R 1 . . C C7 0.19664(17) 0.5780(3) 0.21132(19) 0.0282(9) Uani d . 1 . . H H7A 0.2034 0.6453 0.2037 0.034 Uiso calc R 1 . . H H7B 0.1615 0.5565 0.1615 0.034 Uiso calc R 1 . . C C8 0.26071(16) 0.5276(2) 0.21309(17) 0.0205(8) Uani d . 1 . . C C9 0.28912(17) 0.5404(2) 0.14735(18) 0.0232(8) Uani d . 1 . . H H9 0.2686 0.5807 0.1021 0.028 Uiso calc R 1 . . C C10 0.34729(18) 0.4943(2) 0.14809(19) 0.0261(9) Uani d . 1 . . H H10 0.3672 0.5025 0.1035 0.031 Uiso calc R 1 . . C C11 0.37652(18) 0.4357(2) 0.21491(18) 0.0260(8) Uani d . 1 . . H H11 0.4166 0.4032 0.2171 0.031 Uiso calc R 1 . . C C12 0.34536(17) 0.4261(2) 0.27805(18) 0.0233(8) Uani d . 1 . . H H12 0.3648 0.386 0.3237 0.028 Uiso calc R 1 . . C C13 0.17209(17) 0.6551(2) 0.3317(2) 0.0255(8) Uani d . 1 . . H H13A 0.1438 0.6485 0.3705 0.031 Uiso calc R 1 . . H H13B 0.153 0.7052 0.2912 0.031 Uiso calc R 1 . . C C14 0.24231(17) 0.6816(2) 0.38129(18) 0.0219(8) Uani d . 1 . . C C15 0.26103(18) 0.7742(2) 0.39504(18) 0.0258(8) Uani d . 1 . . H H15 0.2309 0.8224 0.3701 0.031 Uiso calc R 1 . . C C16 0.32436(17) 0.7959(3) 0.44569(18) 0.0264(9) Uani d . 1 . . H H16 0.3375 0.8589 0.4571 0.032 Uiso calc R 1 . . C C17 0.36763(17) 0.7246(2) 0.47901(18) 0.0234(8) Uani d . 1 . . H H17 0.4114 0.7376 0.5131 0.028 Uiso calc R 1 . . C C18 0.34617(17) 0.6336(2) 0.46192(18) 0.0212(8) Uani d . 1 . . H H18 0.3765 0.5846 0.4841 0.025 Uiso calc R 1 . . C C19 0.13411(18) 0.4252(2) 0.47671(18) 0.0219(8) Uani d . 1 . . C C20 0.15716(17) 0.3271(2) 0.49505(17) 0.0197(8) Uani d . 1 . . H H20 0.2027 0.3136 0.5005 0.024 Uiso calc R 1 . . C C21 0.11798(16) 0.2581(2) 0.50417(17) 0.0193(8) Uani d . 1 . . H H21 0.0727 0.2716 0.5003 0.023 Uiso calc R 1 . . C C22 0.14137(18) 0.1596(2) 0.52026(18) 0.0210(8) Uani d . 1 . . O O7 1.00143(12) 0.09395(19) 0.91564(11) 0.0393(7) Uani d G 1 . . H H7C 0.9878 0.1446 0.8873 0.059 Uiso d G 1 . . H H7D 0.9753 0.0811 0.9469 0.059 Uiso d G 1 . . O O8 1.00220(13) 0.07141(19) 0.16589(11) 0.0472(8) Uani d G 1 . . H H8A 1.0068 0.0139 0.1521 0.071 Uiso d G 1 . . H H8B 0.9699 0.0975 0.1274 0.071 Uiso d G 1 . . O O2 0.20357(11) 0.14732(16) 0.55472(13) 0.0248(6) Uani d . 1 . . O O6 0.97265(13) 0.25176(18) 0.81730(14) 0.0395(7) Uiso d G 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Mn1 0.0150(3) 0.0177(3) 0.0187(2) 0.0021(2) 0.00373(19) 0.0027(2) N2 0.0176(16) 0.0234(17) 0.0240(13) -0.0007(13) 0.0054(12) 0.0011(12) N4 0.0208(17) 0.0213(18) 0.0232(13) 0.0027(14) 0.0060(12) 0.0025(12) N1 0.0183(16) 0.0228(17) 0.0181(13) 0.0012(13) 0.0021(11) 0.0015(11) N3 0.0192(17) 0.0210(17) 0.0203(13) 0.0029(13) 0.0059(12) 0.0040(12) O1 0.0208(14) 0.0191(14) 0.0264(11) -0.0005(11) 0.0070(10) 0.0000(10) O4 0.0246(16) 0.0327(17) 0.0700(18) 0.0111(13) 0.0256(14) 0.0163(13) O3 0.0274(15) 0.0204(15) 0.0381(13) -0.0023(12) 0.0095(11) -0.0059(11) O5 0.0289(16) 0.0269(16) 0.0404(14) 0.0072(12) 0.0146(12) 0.0084(11) C1 0.020(2) 0.022(2) 0.0253(16) 0.0004(17) 0.0005(14) 0.0018(14) C2 0.020(2) 0.023(2) 0.0202(15) 0.0001(16) 0.0047(14) 0.0015(14) C3 0.021(2) 0.030(2) 0.0254(17) 0.0028(17) 0.0023(15) 0.0036(15) C4 0.029(2) 0.031(2) 0.0285(18) -0.0066(18) 0.0039(16) -0.0052(16) C5 0.034(2) 0.019(2) 0.0268(17) 0.0008(18) 0.0107(16) 0.0026(15) C6 0.021(2) 0.024(2) 0.0221(16) 0.0000(17) 0.0068(14) -0.0004(14) C7 0.026(2) 0.032(2) 0.0266(17) 0.0035(18) 0.0063(15) 0.0082(15) C8 0.0199(19) 0.019(2) 0.0196(15) -0.0035(16) 0.0010(13) -0.0027(14) C9 0.028(2) 0.022(2) 0.0169(15) -0.0069(18) 0.0027(14) -0.0005(14) C10 0.028(2) 0.033(2) 0.0182(16) -0.0073(18) 0.0089(15) -0.0056(14) C11 0.024(2) 0.032(2) 0.0241(17) 0.0033(17) 0.0097(15) -0.0037(15) C12 0.020(2) 0.028(2) 0.0216(16) 0.0036(17) 0.0043(14) 0.0002(14) C13 0.022(2) 0.017(2) 0.0343(18) 0.0042(16) 0.0029(15) 0.0018(15) C14 0.022(2) 0.021(2) 0.0211(15) 0.0008(17) 0.0045(14) 0.0020(14) C15 0.029(2) 0.019(2) 0.0273(17) 0.0026(17) 0.0045(16) 0.0016(14) C16 0.032(2) 0.021(2) 0.0264(17) -0.0060(17) 0.0087(16) -0.0008(15) C17 0.022(2) 0.023(2) 0.0236(16) -0.0040(17) 0.0032(14) -0.0022(14) C18 0.018(2) 0.027(2) 0.0190(15) 0.0016(16) 0.0054(14) 0.0027(14) C19 0.024(2) 0.022(2) 0.0189(15) 0.0019(17) 0.0051(15) -0.0010(14) C20 0.0174(19) 0.023(2) 0.0183(15) 0.0054(16) 0.0041(13) 0.0001(14) C21 0.0148(19) 0.023(2) 0.0199(15) 0.0029(16) 0.0041(14) 0.0003(13) C22 0.023(2) 0.024(2) 0.0187(15) 0.0004(18) 0.0105(15) -0.0004(14) O7 0.0304(16) 0.0439(18) 0.0424(14) -0.0046(14) 0.0081(12) 0.0010(12) O8 0.0448(19) 0.0385(18) 0.0536(16) 0.0000(15) 0.0055(14) 0.0000(13) O2 0.0198(15) 0.0260(15) 0.0292(12) 0.0071(11) 0.0079(11) 0.0101(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Mn1 O2 7_556 2.088(2) ? Mn1 O1 . 2.133(2) ? Mn1 N1 . 2.244(3) ? Mn1 N3 . 2.265(3) ? Mn1 N4 . 2.303(3) ? Mn1 N2 . 2.354(3) ? N2 C7 . 1.474(4) ? N2 C1 . 1.480(4) ? N2 C13 . 1.483(4) ? N4 C2 . 1.348(4) ? N4 C6 . 1.352(4) ? N1 C12 . 1.344(4) ? N1 C8 . 1.345(4) ? N3 C14 . 1.349(4) ? N3 C18 . 1.358(4) ? O1 C19 . 1.277(4) ? O4 C19 . 1.247(4) ? O3 C22 . 1.245(4) ? O5 H5A . 0.8701 ? O5 H5B . 0.8701 ? C1 C2 . 1.508(5) ? C1 H1A . 0.99 ? C1 H1B . 0.99 ? C2 C3 . 1.391(5) ? C3 C4 . 1.376(5) ? C3 H3 . 0.95 ? C4 C5 . 1.387(5) ? C4 H4 . 0.95 ? C5 C6 . 1.374(5) ? C5 H5 . 0.95 ? C6 H6 . 0.95 ? C7 C8 . 1.515(5) ? C7 H7A . 0.99 ? C7 H7B . 0.99 ? C8 C9 . 1.389(4) ? C9 C10 . 1.380(5) ? C9 H9 . 0.95 ? C10 C11 . 1.391(5) ? C10 H10 . 0.95 ? C11 C12 . 1.383(4) ? C11 H11 . 0.95 ? C12 H12 . 0.95 ? C13 C14 . 1.518(5) ? C13 H13A . 0.99 ? C13 H13B . 0.99 ? C14 C15 . 1.387(5) ? C15 C16 . 1.392(5) ? C15 H15 . 0.95 ? C16 C17 . 1.376(5) ? C16 H16 . 0.95 ? C17 C18 . 1.386(5) ? C17 H17 . 0.95 ? C18 H18 . 0.95 ? C19 C20 . 1.492(4) ? C20 C21 . 1.321(4) ? C20 H20 . 0.95 ? C21 C22 . 1.496(4) ? C21 H21 . 0.95 ? C22 O2 . 1.279(4) ? O7 H7C . 0.87 ? O7 H7D . 0.8701 ? O8 H8A . 0.8701 ? O8 H8B . 0.8753 ? O2 Mn1 7_556 2.088(2) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 Mn1 O1 7_556 . 99.28(8) ? O2 Mn1 N1 7_556 . 95.99(9) ? O1 Mn1 N1 . . 163.69(9) ? O2 Mn1 N3 7_556 . 118.79(10) ? O1 Mn1 N3 . . 92.13(9) ? N1 Mn1 N3 . . 85.46(9) ? O2 Mn1 N4 7_556 . 93.98(10) ? O1 Mn1 N4 . . 87.12(9) ? N1 Mn1 N4 . . 86.16(9) ? N3 Mn1 N4 . . 146.82(9) ? O2 Mn1 N2 7_556 . 164.98(9) ? O1 Mn1 N2 . . 87.74(9) ? N1 Mn1 N2 . . 76.09(9) ? N3 Mn1 N2 . . 73.84(9) ? N4 Mn1 N2 . . 72.99(10) ? C7 N2 C1 . . 111.2(2) ? C7 N2 C13 . . 112.4(3) ? C1 N2 C13 . . 110.7(3) ? C7 N2 Mn1 . . 110.8(2) ? C1 N2 Mn1 . . 106.46(18) ? C13 N2 Mn1 . . 104.84(18) ? C2 N4 C6 . . 118.0(3) ? C2 N4 Mn1 . . 116.0(2) ? C6 N4 Mn1 . . 125.8(2) ? C12 N1 C8 . . 118.8(3) ? C12 N1 Mn1 . . 123.99(19) ? C8 N1 Mn1 . . 117.1(2) ? C14 N3 C18 . . 117.7(3) ? C14 N3 Mn1 . . 115.5(2) ? C18 N3 Mn1 . . 126.8(2) ? C19 O1 Mn1 . . 129.4(2) ? H5A O5 H5B . . 109.6 ? N2 C1 C2 . . 111.1(3) ? N2 C1 H1A . . 109.4 ? C2 C1 H1A . . 109.4 ? N2 C1 H1B . . 109.4 ? C2 C1 H1B . . 109.4 ? H1A C1 H1B . . 108.0 ? N4 C2 C3 . . 122.3(3) ? N4 C2 C1 . . 116.1(3) ? C3 C2 C1 . . 121.5(3) ? C4 C3 C2 . . 118.6(3) ? C4 C3 H3 . . 120.7 ? C2 C3 H3 . . 120.7 ? C3 C4 C5 . . 119.8(3) ? C3 C4 H4 . . 120.1 ? C5 C4 H4 . . 120.1 ? C6 C5 C4 . . 118.5(3) ? C6 C5 H5 . . 120.8 ? C4 C5 H5 . . 120.8 ? N4 C6 C5 . . 122.9(3) ? N4 C6 H6 . . 118.6 ? C5 C6 H6 . . 118.6 ? N2 C7 C8 . . 116.2(3) ? N2 C7 H7A . . 108.2 ? C8 C7 H7A . . 108.2 ? N2 C7 H7B . . 108.2 ? C8 C7 H7B . . 108.2 ? H7A C7 H7B . . 107.4 ? N1 C8 C9 . . 121.3(3) ? N1 C8 C7 . . 119.5(3) ? C9 C8 C7 . . 119.2(3) ? C10 C9 C8 . . 119.6(3) ? C10 C9 H9 . . 120.2 ? C8 C9 H9 . . 120.2 ? C9 C10 C11 . . 119.3(3) ? C9 C10 H10 . . 120.4 ? C11 C10 H10 . . 120.4 ? C12 C11 C10 . . 117.9(3) ? C12 C11 H11 . . 121.1 ? C10 C11 H11 . . 121.1 ? N1 C12 C11 . . 123.1(3) ? N1 C12 H12 . . 118.4 ? C11 C12 H12 . . 118.4 ? N2 C13 C14 . . 111.1(3) ? N2 C13 H13A . . 109.4 ? C14 C13 H13A . . 109.4 ? N2 C13 H13B . . 109.4 ? C14 C13 H13B . . 109.4 ? H13A C13 H13B . . 108.0 ? N3 C14 C15 . . 122.1(3) ? N3 C14 C13 . . 116.7(3) ? C15 C14 C13 . . 121.0(3) ? C14 C15 C16 . . 119.4(3) ? C14 C15 H15 . . 120.3 ? C16 C15 H15 . . 120.3 ? C17 C16 C15 . . 119.0(3) ? C17 C16 H16 . . 120.5 ? C15 C16 H16 . . 120.5 ? C16 C17 C18 . . 118.7(3) ? C16 C17 H17 . . 120.6 ? C18 C17 H17 . . 120.6 ? N3 C18 C17 . . 123.0(3) ? N3 C18 H18 . . 118.5 ? C17 C18 H18 . . 118.5 ? O4 C19 O1 . . 122.9(3) ? O4 C19 C20 . . 119.6(3) ? O1 C19 C20 . . 117.6(3) ? C21 C20 C19 . . 123.9(3) ? C21 C20 H20 . . 118.1 ? C19 C20 H20 . . 118.1 ? C20 C21 C22 . . 123.3(3) ? C20 C21 H21 . . 118.4 ? C22 C21 H21 . . 118.4 ? O3 C22 O2 . . 124.9(3) ? O3 C22 C21 . . 118.2(3) ? O2 C22 C21 . . 116.9(3) ? H7C O7 H7D . . 109.5 ? H8A O8 H8B . . 109.6 ? C22 O2 Mn1 . 7_556 132.7(2) ? _database_code_depnum_ccdc_archive 'CCDC 932448' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 _chemical_name_systematic ? _chemical_name_common '[Mn2(tpa)2(succinate)2].6H2O' _chemical_formula_moiety 'C44 H44 Mn2 N8 O8, 6 (H2 O)' _chemical_formula_sum 'C44 H56 Mn2 N8 O14' _chemical_formula_iupac ? _chemical_formula_weight 1030.85 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_operation_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 19.7966(15) _cell_length_b 13.7795(11) _cell_length_c 17.1799(13) _cell_angle_alpha 90 _cell_angle_beta 101.871(3) _cell_angle_gamma 90 _cell_volume 4586.2(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9845 _cell_measurement_theta_min 2.8485 _cell_measurement_theta_max 25.1322 _cell_measurement_temperature 100.(2) _exptl_crystal_description 'block shaped' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.160 _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2152 _exptl_absorpt_coefficient_mu 0.627 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.6899 _exptl_absorpt_correction_T_max 0.7452 _exptl_special_details ; ; _diffrn_ambient_temperature 100.(2) _diffrn_source 'sealed tube' _diffrn_source_type 'fine focus' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEX II' _diffrn_measurement_method 'phi and Omega scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 26788 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0100 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.14 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _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. ; _reflns_number_total 4094 _reflns_number_gt 3995 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_gt 0.1167 _refine_ls_wR_factor_ref 0.1174 _refine_ls_goodness_of_fit_ref 0.919 _refine_ls_restrained_S_all 0.919 _refine_ls_number_reflns 4094 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+26.5215P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.503 _refine_diff_density_min -0.955 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' _computing_data_collection 'APEX2 V2011.4-1 (Bruker AXS)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Bruker AXS)' _computing_publication_material 'SHELXTL (Bruker AXS)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Mn Mn1 0.237364(19) 0.03823(3) 0.86012(2) 0.01877(14) Uani d . 1 . . N N1 0.29568(12) 0.01755(17) 0.76159(12) 0.0226(5) Uani d . 1 . . N N2 0.16939(11) -0.07540(15) 0.77293(13) 0.0196(5) Uani d . 1 . . N N3 0.14968(11) 0.12300(15) 0.77146(12) 0.0211(5) Uani d . 1 . . N N4 0.27810(11) -0.11624(16) 0.90074(12) 0.0196(4) Uani d . 1 . . O O1 0.27716(13) 0.1904(2) 0.88498(14) 0.0519(7) Uani d . 1 . . O O2 0.16687(9) 0.02232(14) 0.93632(11) 0.0244(4) Uani d . 1 . . O O3 0.08937(10) 0.04692(14) 1.00975(13) 0.0292(5) Uani d . 1 . . O O4 0.35051(18) 0.08511(18) 0.94996(14) 0.0617(9) Uani d . 1 . . O O5 0.01028(9) 0.27493(15) 0.17036(13) 0.0362(5) Uani d G 1 . . H H5A -0.0024 0.2213 0.1448 0.054 Uiso d G 1 . . H H5B 0.0035 0.3235 0.1373 0.054 Uiso d G 1 . . O O7 0.47967(9) 0.61274(14) 0.07167(12) 0.0257(4) Uani d G 1 . . C C1 0.35752(15) 0.0578(2) 0.76048(16) 0.0285(6) Uani d . 1 . . H H1 0.3769 0.1008 0.8024 0.034 Uiso calc R 1 . . C C2 0.39401(16) 0.0400(2) 0.70196(17) 0.0305(7) Uani d . 1 . . H H2 0.4377 0.0694 0.7038 0.037 Uiso calc R 1 . . C C3 0.36556(15) -0.0218(2) 0.64019(17) 0.0281(6) Uani d . 1 . . H H3 0.3892 -0.0354 0.5986 0.034 Uiso calc R 1 . . C C4 0.30215(15) -0.06311(19) 0.64062(16) 0.0249(6) Uani d . 1 . . H H4 0.2815 -0.1054 0.5988 0.03 Uiso calc R 1 . . C C5 0.26838(14) -0.04291(18) 0.70229(15) 0.0207(5) Uani d . 1 . . C C6 0.19832(13) -0.08741(19) 0.70055(15) 0.0222(5) Uani d . 1 . . H H6A 0.1653 -0.0591 0.6551 0.027 Uiso calc R 1 . . H H6B 0.2014 -0.1578 0.69 0.027 Uiso calc R 1 . . O O6 1.01428(19) 0.4412(2) 0.06785(19) 0.0719(9) Uani d G 1 . . C C7 0.33724(13) -0.1361(2) 0.95273(15) 0.0225(5) Uani d . 1 . . H H7 0.3664 -0.0837 0.9742 0.027 Uiso calc R 1 . . C C8 0.35743(14) -0.2296(2) 0.97626(16) 0.0265(6) Uani d . 1 . . H H8 0.3993 -0.2407 1.0136 0.032 Uiso calc R 1 . . C C9 0.31600(15) -0.3064(2) 0.94478(16) 0.0264(6) Uani d . 1 . . H H9 0.3286 -0.3712 0.9602 0.032 Uiso calc R 1 . . C C10 0.25569(14) -0.2870(2) 0.89027(16) 0.0239(6) Uani d . 1 . . H H10 0.2265 -0.3385 0.8669 0.029 Uiso calc R 1 . . C C11 0.23820(13) -0.19103(19) 0.87000(15) 0.0200(5) Uani d . 1 . . C C12 0.16914(14) -0.16676(19) 0.81771(17) 0.0260(6) Uani d . 1 . . H H12A 0.1552 -0.2205 0.7795 0.031 Uiso calc R 1 . . H H12B 0.1342 -0.1618 0.8513 0.031 Uiso calc R 1 . . C C13 0.09845(13) -0.03642(18) 0.75149(16) 0.0211(5) Uani d . 1 . . H H13A 0.0754 -0.0446 0.797 0.025 Uiso calc R 1 . . H H13B 0.0719 -0.0737 0.706 0.025 Uiso calc R 1 . . C C14 0.09833(13) 0.06926(19) 0.72951(15) 0.0195(5) Uani d . 1 . . C C15 0.04547(14) 0.1094(2) 0.67270(16) 0.0245(6) Uani d . 1 . . H H15 0.0111 0.0691 0.6419 0.029 Uiso calc R 1 . . C C16 0.04375(16) 0.2089(2) 0.66182(17) 0.0291(6) Uani d . 1 . . H H16 0.0076 0.2381 0.6242 0.035 Uiso calc R 1 . . C C17 0.09539(16) 0.2652(2) 0.70643(17) 0.0291(6) Uani d . 1 . . H H17 0.0948 0.3338 0.701 0.035 Uiso calc R 1 . . C C18 0.14773(15) 0.21944(19) 0.75904(16) 0.0255(6) Uani d . 1 . . H H18 0.1842 0.258 0.788 0.031 Uiso calc R 1 . . C C19 0.13502(13) 0.07720(19) 0.97539(14) 0.0201(5) Uani d . 1 . . C C20 0.15549(14) 0.1836(2) 0.98138(16) 0.0242(6) Uani d . 1 . . H H20A 0.1468 0.2111 0.927 0.029 Uiso calc R 1 . . H H20B 0.2058 0.1876 1.0029 0.029 Uiso calc R 1 . . C C21 0.38097(14) 0.2526(2) 0.96749(15) 0.0247(6) Uani d . 1 . . H H21A 0.424 0.2261 1.0003 0.03 Uiso calc R 1 . . H H21B 0.3933 0.2917 0.9242 0.03 Uiso calc R 1 . . C C22 0.3333(2) 0.1694(2) 0.93222(18) 0.0415(9) Uani d . 1 . . H H7A 0.450(2) 0.574(3) 0.050(3) 0.063(13) Uiso d . 1 . . H H7B 0.513(2) 0.600(3) 0.051(2) 0.047(11) Uiso d . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Mn1 0.0185(2) 0.0221(2) 0.0147(2) -0.00491(15) 0.00110(15) -0.00002(14) N1 0.0256(11) 0.0263(12) 0.0146(10) -0.0063(9) 0.0013(9) 0.0009(9) N2 0.0190(11) 0.0165(11) 0.0212(11) -0.0007(8) -0.0006(8) 0.0025(9) N3 0.0278(12) 0.0180(11) 0.0174(10) -0.0049(9) 0.0044(9) -0.0017(8) N4 0.0212(11) 0.0216(11) 0.0162(10) -0.0007(9) 0.0043(8) 0.0014(8) O1 0.0404(13) 0.0807(19) 0.0347(13) -0.0373(13) 0.0083(11) -0.0230(13) O2 0.0252(10) 0.0243(10) 0.0252(10) -0.0009(8) 0.0088(8) 0.0034(8) O3 0.0292(10) 0.0245(10) 0.0383(11) -0.0111(8) 0.0172(9) -0.0076(8) O4 0.126(3) 0.0330(14) 0.0335(13) -0.0327(15) 0.0328(15) -0.0073(10) O5 0.0471(13) 0.0243(11) 0.0415(12) -0.0047(9) 0.0189(10) -0.0060(9) O7 0.0218(10) 0.0222(10) 0.0318(11) -0.0008(8) 0.0025(9) -0.0071(8) C1 0.0295(15) 0.0364(16) 0.0188(13) -0.0128(12) 0.0035(11) -0.0022(12) C2 0.0312(15) 0.0381(17) 0.0229(14) -0.0102(12) 0.0073(12) 0.0017(12) C3 0.0356(15) 0.0282(15) 0.0224(14) -0.0001(12) 0.0102(12) 0.0032(11) C4 0.0348(15) 0.0183(13) 0.0202(13) 0.0002(11) 0.0024(11) -0.0010(10) C5 0.0259(13) 0.0166(12) 0.0168(12) 0.0002(10) -0.0019(10) 0.0043(10) C6 0.0233(13) 0.0189(13) 0.0219(13) -0.0004(10) -0.0013(10) -0.0043(10) O6 0.096(2) 0.0582(18) 0.0602(19) 0.0179(17) 0.0127(17) 0.0146(15) C7 0.0223(13) 0.0279(14) 0.0166(12) 0.0008(11) 0.0027(10) 0.0002(10) C8 0.0263(14) 0.0331(15) 0.0196(13) 0.0070(12) 0.0032(11) 0.0037(11) C9 0.0333(15) 0.0234(14) 0.0233(14) 0.0078(11) 0.0078(12) 0.0060(11) C10 0.0290(14) 0.0211(13) 0.0228(13) -0.0003(11) 0.0082(11) 0.0028(11) C11 0.0212(13) 0.0214(13) 0.0180(12) 0.0005(10) 0.0051(10) 0.0036(10) C12 0.0246(14) 0.0189(13) 0.0319(15) -0.0038(11) -0.0002(11) 0.0059(11) C13 0.0181(12) 0.0187(13) 0.0241(13) -0.0025(10) -0.0017(10) 0.0003(10) C14 0.0213(13) 0.0196(13) 0.0177(12) -0.0020(10) 0.0039(10) -0.0017(10) C15 0.0251(13) 0.0256(14) 0.0220(13) 0.0016(11) 0.0027(11) -0.0004(11) C16 0.0350(16) 0.0270(15) 0.0247(14) 0.0078(12) 0.0048(12) 0.0057(11) C17 0.0456(17) 0.0182(13) 0.0268(14) 0.0030(12) 0.0150(13) 0.0036(11) C18 0.0391(16) 0.0181(13) 0.0210(13) -0.0079(11) 0.0105(12) -0.0043(10) C19 0.0172(12) 0.0262(14) 0.0145(12) -0.0045(10) -0.0026(10) 0.0022(10) C20 0.0257(13) 0.0256(14) 0.0206(13) -0.0091(11) 0.0031(10) 0.0025(11) C21 0.0308(14) 0.0252(14) 0.0175(12) -0.0114(11) 0.0033(11) -0.0024(11) C22 0.072(2) 0.0380(19) 0.0231(15) -0.0264(17) 0.0308(17) -0.0074(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Mn1 O2 . 2.1122(18) ? Mn1 O1 . 2.249(3) ? Mn1 N1 . 2.255(2) ? Mn1 N4 . 2.332(2) ? Mn1 N3 . 2.369(2) ? Mn1 N2 . 2.383(2) ? Mn1 O4 . 2.529(3) ? N1 C5 . 1.341(3) ? N1 C1 . 1.348(4) ? N2 C12 . 1.476(3) ? N2 C13 . 1.478(3) ? N2 C6 . 1.482(3) ? N3 C14 . 1.342(3) ? N3 C18 . 1.345(3) ? N4 C11 . 1.339(3) ? N4 C7 . 1.347(3) ? O1 C22 . 1.267(5) ? O2 C19 . 1.263(3) ? O3 C19 . 1.248(3) ? O4 C22 . 1.231(5) ? O5 H5A . 0.87 ? O5 H5B . 0.87 ? O7 H7A . 0.83(5) ? O7 H7B . 0.84(4) ? C1 C2 . 1.375(4) ? C1 H1 . 0.95 ? C2 C3 . 1.387(4) ? C2 H2 . 0.95 ? C3 C4 . 1.380(4) ? C3 H3 . 0.95 ? C4 C5 . 1.392(4) ? C4 H4 . 0.95 ? C5 C6 . 1.511(4) ? C6 H6A . 0.99 ? C6 H6B . 0.99 ? C7 C8 . 1.383(4) ? C7 H7 . 0.95 ? C8 C9 . 1.380(4) ? C8 H8 . 0.95 ? C9 C10 . 1.384(4) ? C9 H9 . 0.95 ? C10 C11 . 1.393(4) ? C10 H10 . 0.95 ? C11 C12 . 1.511(4) ? C12 H12A . 0.99 ? C12 H12B . 0.99 ? C13 C14 . 1.504(4) ? C13 H13A . 0.99 ? C13 H13B . 0.99 ? C14 C15 . 1.390(4) ? C15 C16 . 1.383(4) ? C15 H15 . 0.95 ? C16 C17 . 1.383(4) ? C16 H16 . 0.95 ? C17 C18 . 1.379(4) ? C17 H17 . 0.95 ? C18 H18 . 0.95 ? C19 C20 . 1.519(4) ? C20 C21 7_557 1.525(4) ? C20 H20A . 0.99 ? C20 H20B . 0.99 ? C21 C20 7_557 1.525(4) ? C21 C22 . 1.529(4) ? C21 H21A . 0.99 ? C21 H21B . 0.99 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 Mn1 O1 . . 103.25(8) ? O2 Mn1 N1 . . 163.31(8) ? O1 Mn1 N1 . . 92.69(8) ? O2 Mn1 N4 . . 87.23(7) ? O1 Mn1 N4 . . 135.06(9) ? N1 Mn1 N4 . . 84.86(8) ? O2 Mn1 N3 . . 87.68(7) ? O1 Mn1 N3 . . 81.04(9) ? N1 Mn1 N3 . . 90.01(8) ? N4 Mn1 N3 . . 143.64(8) ? O2 Mn1 N2 . . 87.81(8) ? O1 Mn1 N2 . . 149.58(9) ? N1 Mn1 N2 . . 75.83(8) ? N4 Mn1 N2 . . 72.79(7) ? N3 Mn1 N2 . . 71.06(7) ? O2 Mn1 O4 . . 105.27(8) ? O1 Mn1 O4 . . 54.15(9) ? N1 Mn1 O4 . . 87.97(8) ? N4 Mn1 O4 . . 80.91(8) ? N3 Mn1 O4 . . 134.95(8) ? N2 Mn1 O4 . . 150.05(9) ? C5 N1 C1 . . 118.1(2) ? C5 N1 Mn1 . . 117.42(18) ? C1 N1 Mn1 . . 124.43(18) ? C12 N2 C13 . . 109.6(2) ? C12 N2 C6 . . 112.7(2) ? C13 N2 C6 . . 110.1(2) ? C12 N2 Mn1 . . 107.15(15) ? C13 N2 Mn1 . . 107.63(15) ? C6 N2 Mn1 . . 109.59(15) ? C14 N3 C18 . . 117.8(2) ? C14 N3 Mn1 . . 116.58(17) ? C18 N3 Mn1 . . 125.63(18) ? C11 N4 C7 . . 117.8(2) ? C11 N4 Mn1 . . 116.42(16) ? C7 N4 Mn1 . . 125.77(18) ? C22 O1 Mn1 . . 97.8(2) ? C19 O2 Mn1 . . 137.17(17) ? C22 O4 Mn1 . . 85.7(2) ? H5A O5 H5B . . 109.6 ? H7A O7 H7B . . 103.(4) ? N1 C1 C2 . . 123.5(3) ? N1 C1 H1 . . 118.2 ? C2 C1 H1 . . 118.2 ? C1 C2 C3 . . 118.5(3) ? C1 C2 H2 . . 120.7 ? C3 C2 H2 . . 120.7 ? C4 C3 C2 . . 118.4(3) ? C4 C3 H3 . . 120.8 ? C2 C3 H3 . . 120.8 ? C3 C4 C5 . . 120.1(3) ? C3 C4 H4 . . 120.0 ? C5 C4 H4 . . 120.0 ? N1 C5 C4 . . 121.4(2) ? N1 C5 C6 . . 119.5(2) ? C4 C5 C6 . . 119.1(2) ? N2 C6 C5 . . 116.7(2) ? N2 C6 H6A . . 108.1 ? C5 C6 H6A . . 108.1 ? N2 C6 H6B . . 108.1 ? C5 C6 H6B . . 108.1 ? H6A C6 H6B . . 107.3 ? N4 C7 C8 . . 122.9(3) ? N4 C7 H7 . . 118.6 ? C8 C7 H7 . . 118.6 ? C9 C8 C7 . . 119.1(3) ? C9 C8 H8 . . 120.4 ? C7 C8 H8 . . 120.4 ? C8 C9 C10 . . 118.5(3) ? C8 C9 H9 . . 120.7 ? C10 C9 H9 . . 120.7 ? C9 C10 C11 . . 119.2(3) ? C9 C10 H10 . . 120.4 ? C11 C10 H10 . . 120.4 ? N4 C11 C10 . . 122.4(2) ? N4 C11 C12 . . 116.9(2) ? C10 C11 C12 . . 120.4(2) ? N2 C12 C11 . . 113.5(2) ? N2 C12 H12A . . 108.9 ? C11 C12 H12A . . 108.9 ? N2 C12 H12B . . 108.9 ? C11 C12 H12B . . 108.9 ? H12A C12 H12B . . 107.7 ? N2 C13 C14 . . 111.5(2) ? N2 C13 H13A . . 109.3 ? C14 C13 H13A . . 109.3 ? N2 C13 H13B . . 109.3 ? C14 C13 H13B . . 109.3 ? H13A C13 H13B . . 108.0 ? N3 C14 C15 . . 122.4(2) ? N3 C14 C13 . . 115.9(2) ? C15 C14 C13 . . 121.5(2) ? C16 C15 C14 . . 118.9(3) ? C16 C15 H15 . . 120.6 ? C14 C15 H15 . . 120.6 ? C17 C16 C15 . . 119.1(3) ? C17 C16 H16 . . 120.5 ? C15 C16 H16 . . 120.5 ? C18 C17 C16 . . 118.5(3) ? C18 C17 H17 . . 120.7 ? C16 C17 H17 . . 120.7 ? N3 C18 C17 . . 123.3(3) ? N3 C18 H18 . . 118.4 ? C17 C18 H18 . . 118.4 ? O3 C19 O2 . . 122.7(2) ? O3 C19 C20 . . 120.0(2) ? O2 C19 C20 . . 117.3(2) ? C19 C20 C21 . 7_557 116.4(2) ? C19 C20 H20A . . 108.2 ? C21 C20 H20A 7_557 . 108.2 ? C19 C20 H20B . . 108.2 ? C21 C20 H20B 7_557 . 108.2 ? H20A C20 H20B . . 107.4 ? C20 C21 C22 7_557 . 109.5(2) ? C20 C21 H21A 7_557 . 109.8 ? C22 C21 H21A . . 109.8 ? C20 C21 H21B 7_557 . 109.8 ? C22 C21 H21B . . 109.8 ? H21A C21 H21B . . 108.2 ? O4 C22 O1 . . 122.4(3) ? O4 C22 C21 . . 119.5(3) ? O1 C22 C21 . . 118.1(3) ? #===END _database_code_depnum_ccdc_archive 'CCDC 932449'