# 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_mnvrlb _nottingham_internal_coll_name MNVRLB _nottingham_internal_coll_number 9490 _nottingham_internal_coll_client VJR/NRC _nottingham_internal_coll_type hemisphere _nottingham_internal_coll_frame_time '120 s' _nottingham_internal_coll_frame_width '0.3 degrees' _nottingham_internal_coll_frame_method \w _nottingham_internal_coll_user VJR/AJB _nottingham_internal_coll_date 25/06/10 _nottingham_internal_process_user WL _nottingham_internal_process_date 29/06/2010 _nottingham_internal_solution_user WL _nottingham_internal_solution_date 29/06/2010 _nottingham_internal_refinement_user VJR _nottingham_internal_refinement_date 14/09/2010 _nottingham_internal_validation_user AJB _nottingham_internal_validation_date 21/10/2010 _nottingham_internal_archive_date ? _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H22 N6 O4' _chemical_formula_sum 'C26 H22 N6 O4' _chemical_formula_weight 482.50 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' _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 12.2465(18) _cell_length_b 8.9751(13) _cell_length_c 21.857(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.809(6) _cell_angle_gamma 90.00 _cell_volume 2144.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 2666 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.008 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method ? _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.606 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details 'SADABS 2007/2' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10773 _diffrn_reflns_av_R_equivalents 0.046 _diffrn_reflns_av_sigmaI/netI 0.059 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3804 _reflns_number_gt 3272 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36A (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'Bruker SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics ' ?' _computing_publication_material 'enCIFer (Allen et al., 2004); PLATON (Spek, 2009)' _refine_special_details ; ; _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^)+(0.028P)^2^+5.568P] 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 3804 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.110 _refine_ls_R_factor_gt 0.0957 _refine_ls_wR_factor_ref 0.173 _refine_ls_wR_factor_gt 0.167 _refine_ls_goodness_of_fit_ref 1.29 _refine_ls_restrained_S_all 1.29 _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 C11 C 0.7474(4) 0.1523(5) 0.4580(2) 0.0176(9) Uani 1 1 d . . . C12 C 0.7280(4) 0.0486(5) 0.4075(2) 0.0197(9) Uani 1 1 d . . . H12A H 0.6519 -0.0023 0.3862 0.024 Uiso 1 1 calc R . . C13 C 0.8188(4) 0.0170(5) 0.3870(2) 0.0179(9) Uani 1 1 d . . . H13A H 0.8043 -0.0563 0.3528 0.021 Uiso 1 1 calc R . . C14 C 0.9289(4) 0.0914(5) 0.4161(2) 0.0189(9) Uani 1 1 d . . . C15 C 1.0646(4) 0.2730(5) 0.4995(2) 0.0169(9) Uani 1 1 d . . . C16 C 1.0877(4) 0.3684(5) 0.5536(2) 0.0192(9) Uani 1 1 d . . . H16A H 1.1646 0.4175 0.5755 0.023 Uiso 1 1 calc R . . C17 C 1.0001(4) 0.3938(5) 0.5766(2) 0.0180(9) Uani 1 1 d . . . H17A H 1.0182 0.4589 0.6142 0.022 Uiso 1 1 calc R . . C18 C 0.8876(4) 0.3254(5) 0.5451(2) 0.0168(9) Uani 1 1 d . . . C19 C 0.8614(4) 0.2271(5) 0.4896(2) 0.0177(9) Uani 1 1 d . . . C20 C 0.9514(4) 0.1986(5) 0.4678(2) 0.0173(9) Uani 1 1 d . . . C21 C 0.6512(4) 0.1835(5) 0.4792(2) 0.0182(9) Uani 1 1 d . . . O22 O 0.5516(3) 0.1231(3) 0.45307(15) 0.0215(7) Uani 1 1 d . . . N23 N 0.6793(3) 0.2874(4) 0.53123(17) 0.0176(8) Uani 1 1 d . . . C24 C 0.7947(4) 0.3541(5) 0.5693(2) 0.0182(9) Uani 1 1 d . . . O25 O 0.8148(3) 0.4286(3) 0.61926(15) 0.0214(7) Uani 1 1 d . . . C26 C 1.0250(4) 0.0571(4) 0.3948(2) 0.0152(9) Uani 1 1 d . . . O27 O 1.0125(3) -0.0410(3) 0.35386(15) 0.0223(7) Uani 1 1 d . . . N28 N 1.1347(3) 0.1389(4) 0.42599(17) 0.0177(8) Uani 1 1 d . . . C29 C 1.1586(4) 0.2476(5) 0.4755(2) 0.0176(9) Uani 1 1 d . . . O30 O 1.2555(2) 0.3155(3) 0.49949(14) 0.0211(7) Uani 1 1 d . . . C31 C 0.5858(4) 0.3208(5) 0.5545(2) 0.0176(9) Uani 1 1 d . . . H31A H 0.5034 0.3080 0.5157 0.021 Uiso 1 1 calc R . . H31B H 0.5941 0.4259 0.5696 0.021 Uiso 1 1 calc R . . C32 C 0.5980(4) 0.2202(5) 0.6132(2) 0.0172(9) Uani 1 1 d . . . H32A H 0.5812 0.1160 0.5966 0.021 Uiso 1 1 calc R . . H32B H 0.6832 0.2248 0.6500 0.021 Uiso 1 1 calc R . . C33 C 0.5115(4) 0.2637(5) 0.6424(2) 0.0180(9) Uani 1 1 d . . . H33A H 0.4262 0.2546 0.6061 0.022 Uiso 1 1 calc R . . H33B H 0.5221 0.1938 0.6797 0.022 Uiso 1 1 calc R . . N41 N 0.5324(3) 0.4160(4) 0.66916(17) 0.0165(8) Uani 1 1 d . . . C42 C 0.6340(4) 0.4685(5) 0.7231(2) 0.0233(10) Uani 1 1 d . . . H42A H 0.7046 0.4098 0.7487 0.028 Uiso 1 1 calc R . . N43 N 0.6241(3) 0.6097(4) 0.73600(18) 0.0218(8) Uani 1 1 d . . . C44 C 0.5103(4) 0.6510(5) 0.6871(2) 0.0236(10) Uani 1 1 d . . . H44A H 0.4762 0.7478 0.6827 0.028 Uiso 1 1 calc R . . C45 C 0.4533(4) 0.5336(5) 0.6459(2) 0.0219(10) Uani 1 1 d . . . H45A H 0.3739 0.5333 0.6083 0.026 Uiso 1 1 calc R . . C51 C 1.2336(4) 0.1029(5) 0.4075(2) 0.0210(10) Uani 1 1 d . . . H51A H 1.2202 0.0010 0.3881 0.025 Uiso 1 1 calc R . . H51B H 1.3125 0.1030 0.4497 0.025 Uiso 1 1 calc R . . C52 C 1.2423(4) 0.2111(5) 0.3558(2) 0.0175(9) Uani 1 1 d . . . H52A H 1.2358 0.3142 0.3700 0.021 Uiso 1 1 calc R . . H52B H 1.3239 0.2004 0.3573 0.021 Uiso 1 1 calc R . . C53 C 1.1450(4) 0.1884(5) 0.2825(2) 0.0156(9) Uani 1 1 d . . . H53A H 1.0636 0.1859 0.2817 0.019 Uiso 1 1 calc R . . H53B H 1.1464 0.2742 0.2544 0.019 Uiso 1 1 calc R . . N61 N 1.1624(3) 0.0509(4) 0.25186(16) 0.0130(7) Uani 1 1 d . . . C62 C 1.0923(4) -0.0732(5) 0.2371(2) 0.0172(9) Uani 1 1 d . . . H62A H 1.0253 -0.0848 0.2474 0.021 Uiso 1 1 calc R . . N63 N 1.1276(3) -0.1766(4) 0.20670(17) 0.0207(8) Uani 1 1 d . . . C64 C 1.2259(4) -0.1138(5) 0.2023(2) 0.0173(9) Uani 1 1 d . . . H64A H 1.2720 -0.1614 0.1827 0.021 Uiso 1 1 calc R . . C65 C 1.2487(4) 0.0255(5) 0.2298(2) 0.0173(9) Uani 1 1 d . . . H65A H 1.3118 0.0914 0.2330 0.021 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C11 0.020(2) 0.012(2) 0.018(2) 0.0037(17) 0.0063(18) -0.0001(17) C12 0.020(2) 0.020(2) 0.013(2) 0.0064(18) 0.0027(18) -0.0027(18) C13 0.025(2) 0.015(2) 0.011(2) 0.0050(17) 0.0058(18) 0.0002(18) C14 0.022(2) 0.013(2) 0.019(2) 0.0062(17) 0.0063(19) -0.0007(17) C15 0.017(2) 0.015(2) 0.012(2) 0.0034(17) 0.0011(17) 0.0056(17) C16 0.019(2) 0.019(2) 0.016(2) 0.0008(18) 0.0057(18) -0.0029(18) C17 0.024(2) 0.010(2) 0.017(2) -0.0013(17) 0.0063(19) -0.0011(17) C18 0.020(2) 0.013(2) 0.017(2) 0.0047(17) 0.0073(18) 0.0015(17) C19 0.021(2) 0.015(2) 0.014(2) 0.0070(17) 0.0062(18) 0.0062(17) C20 0.020(2) 0.011(2) 0.016(2) 0.0052(17) 0.0047(18) 0.0012(17) C21 0.019(2) 0.014(2) 0.017(2) 0.0030(18) 0.0049(18) -0.0023(18) O22 0.0192(16) 0.0236(17) 0.0217(16) -0.0007(13) 0.0091(13) -0.0060(13) N23 0.0176(18) 0.0173(19) 0.0169(19) 0.0018(15) 0.0069(15) 0.0020(15) C24 0.024(2) 0.017(2) 0.012(2) 0.0026(18) 0.0070(18) 0.0018(18) O25 0.0244(16) 0.0212(17) 0.0187(16) -0.0034(14) 0.0097(13) -0.0022(13) C26 0.020(2) 0.013(2) 0.0077(19) 0.0035(17) 0.0019(17) 0.0025(17) O27 0.0267(17) 0.0197(17) 0.0202(16) -0.0035(14) 0.0104(14) -0.0006(13) N28 0.0160(18) 0.0191(19) 0.0178(19) -0.0001(15) 0.0075(15) 0.0011(15) C29 0.018(2) 0.018(2) 0.013(2) 0.0056(17) 0.0029(18) 0.0061(18) O30 0.0124(15) 0.0285(18) 0.0179(16) -0.0041(13) 0.0030(12) -0.0016(13) C31 0.018(2) 0.016(2) 0.016(2) 0.0022(17) 0.0048(18) -0.0005(17) C32 0.017(2) 0.015(2) 0.017(2) -0.0023(17) 0.0059(18) -0.0032(17) C33 0.016(2) 0.016(2) 0.018(2) -0.0007(17) 0.0042(18) -0.0040(17) N41 0.0145(17) 0.0179(19) 0.0177(19) 0.0008(15) 0.0080(15) 0.0008(14) C42 0.024(2) 0.024(2) 0.014(2) -0.0022(18) 0.0011(19) 0.0021(19) N43 0.024(2) 0.020(2) 0.0172(19) -0.0014(15) 0.0056(16) 0.0015(16) C44 0.020(2) 0.021(2) 0.029(3) 0.005(2) 0.010(2) 0.0065(19) C45 0.012(2) 0.023(2) 0.026(2) 0.001(2) 0.0047(19) 0.0044(18) C51 0.020(2) 0.022(2) 0.019(2) -0.0015(19) 0.0063(19) 0.0033(18) C52 0.015(2) 0.020(2) 0.017(2) -0.0043(18) 0.0066(17) 0.0004(18) C53 0.018(2) 0.013(2) 0.019(2) -0.0008(17) 0.0110(18) 0.0001(17) N61 0.0150(17) 0.0134(18) 0.0121(17) 0.0022(14) 0.0076(14) -0.0004(14) C62 0.017(2) 0.018(2) 0.020(2) 0.0016(18) 0.0115(18) -0.0016(17) N63 0.028(2) 0.020(2) 0.0142(18) 0.0002(15) 0.0095(16) -0.0027(16) C64 0.017(2) 0.023(2) 0.013(2) 0.0053(18) 0.0079(18) 0.0048(18) C65 0.015(2) 0.021(2) 0.014(2) 0.0024(18) 0.0046(17) 0.0004(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 C12 1.380(6) . ? C11 C19 1.417(6) . ? C11 C21 1.475(6) . ? C12 C13 1.403(6) . ? C12 H12A 0.9500 . ? C13 C14 1.377(6) . ? C13 H13A 0.9500 . ? C14 C20 1.414(6) . ? C14 C26 1.481(6) . ? C15 C16 1.381(6) . ? C15 C20 1.407(6) . ? C15 C29 1.482(6) . ? C16 C17 1.393(6) . ? C16 H16A 0.9500 . ? C17 C18 1.377(6) . ? C17 H17A 0.9500 . ? C18 C19 1.415(6) . ? C18 C24 1.478(6) . ? C19 C20 1.407(6) . ? C21 O22 1.216(5) . ? C21 N23 1.388(5) . ? N23 C24 1.409(5) . ? N23 C31 1.478(5) . ? C24 O25 1.207(5) . ? C26 O27 1.214(5) . ? C26 N28 1.408(5) . ? N28 C29 1.387(5) . ? N28 C51 1.474(5) . ? C29 O30 1.222(5) . ? C31 C32 1.519(6) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.514(6) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 N41 1.463(5) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? N41 C42 1.355(5) . ? N41 C45 1.366(5) . ? C42 N43 1.316(6) . ? C42 H42A 0.9500 . ? N43 C44 1.370(5) . ? C44 C45 1.356(6) . ? C44 H44A 0.9500 . ? C45 H45A 0.9500 . ? C51 C52 1.530(6) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 C53 1.519(5) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 N61 1.464(5) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? N61 C62 1.353(5) . ? N61 C65 1.365(5) . ? C62 N63 1.322(5) . ? C62 H62A 0.9500 . ? N63 C64 1.371(5) . ? C64 C65 1.360(6) . ? C64 H64A 0.9500 . ? C65 H65A 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 C12 C11 C19 119.1(4) . . ? C12 C11 C21 120.4(4) . . ? C19 C11 C21 120.5(4) . . ? C11 C12 C13 121.1(4) . . ? C11 C12 H12A 119.4 . . ? C13 C12 H12A 119.4 . . ? C14 C13 C12 120.4(4) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C13 C14 C20 119.8(4) . . ? C13 C14 C26 120.3(4) . . ? C20 C14 C26 119.8(4) . . ? C16 C15 C20 119.4(4) . . ? C16 C15 C29 120.4(4) . . ? C20 C15 C29 120.2(4) . . ? C15 C16 C17 121.0(4) . . ? C15 C16 H16A 119.5 . . ? C17 C16 H16A 119.5 . . ? C18 C17 C16 120.5(4) . . ? C18 C17 H17A 119.8 . . ? C16 C17 H17A 119.8 . . ? C17 C18 C19 119.7(4) . . ? C17 C18 C24 120.2(4) . . ? C19 C18 C24 120.2(4) . . ? C20 C19 C18 119.6(4) . . ? C20 C19 C11 119.9(4) . . ? C18 C19 C11 120.4(4) . . ? C15 C20 C19 119.7(4) . . ? C15 C20 C14 120.6(4) . . ? C19 C20 C14 119.6(4) . . ? O22 C21 N23 120.7(4) . . ? O22 C21 C11 122.8(4) . . ? N23 C21 C11 116.6(4) . . ? C21 N23 C24 125.5(3) . . ? C21 N23 C31 118.3(3) . . ? C24 N23 C31 115.9(3) . . ? O25 C24 N23 120.7(4) . . ? O25 C24 C18 123.0(4) . . ? N23 C24 C18 116.3(4) . . ? O27 C26 N28 120.8(4) . . ? O27 C26 C14 121.9(4) . . ? N28 C26 C14 117.3(4) . . ? C29 N28 C26 124.4(3) . . ? C29 N28 C51 117.2(3) . . ? C26 N28 C51 118.3(3) . . ? O30 C29 N28 120.5(4) . . ? O30 C29 C15 122.0(4) . . ? N28 C29 C15 117.4(4) . . ? N23 C31 C32 111.9(3) . . ? N23 C31 H31A 109.2 . . ? C32 C31 H31A 109.2 . . ? N23 C31 H31B 109.2 . . ? C32 C31 H31B 109.2 . . ? H31A C31 H31B 107.9 . . ? C33 C32 C31 112.4(3) . . ? C33 C32 H32A 109.1 . . ? C31 C32 H32A 109.1 . . ? C33 C32 H32B 109.1 . . ? C31 C32 H32B 109.1 . . ? H32A C32 H32B 107.9 . . ? N41 C33 C32 112.3(3) . . ? N41 C33 H33A 109.1 . . ? C32 C33 H33A 109.1 . . ? N41 C33 H33B 109.1 . . ? C32 C33 H33B 109.1 . . ? H33A C33 H33B 107.9 . . ? C42 N41 C45 105.8(4) . . ? C42 N41 C33 126.8(4) . . ? C45 N41 C33 127.4(4) . . ? N43 C42 N41 112.6(4) . . ? N43 C42 H42A 123.7 . . ? N41 C42 H42A 123.7 . . ? C42 N43 C44 104.6(4) . . ? C45 C44 N43 110.2(4) . . ? C45 C44 H44A 124.9 . . ? N43 C44 H44A 124.9 . . ? C44 C45 N41 106.7(4) . . ? C44 C45 H45A 126.7 . . ? N41 C45 H45A 126.7 . . ? N28 C51 C52 113.7(3) . . ? N28 C51 H51A 108.8 . . ? C52 C51 H51A 108.8 . . ? N28 C51 H51B 108.8 . . ? C52 C51 H51B 108.8 . . ? H51A C51 H51B 107.7 . . ? C53 C52 C51 114.3(3) . . ? C53 C52 H52A 108.7 . . ? C51 C52 H52A 108.7 . . ? C53 C52 H52B 108.7 . . ? C51 C52 H52B 108.7 . . ? H52A C52 H52B 107.6 . . ? N61 C53 C52 112.9(3) . . ? N61 C53 H53A 109.0 . . ? C52 C53 H53A 109.0 . . ? N61 C53 H53B 109.0 . . ? C52 C53 H53B 109.0 . . ? H53A C53 H53B 107.8 . . ? C62 N61 C65 106.7(3) . . ? C62 N61 C53 126.6(3) . . ? C65 N61 C53 126.7(3) . . ? N63 C62 N61 112.4(3) . . ? N63 C62 H62A 123.8 . . ? N61 C62 H62A 123.8 . . ? C62 N63 C64 104.1(3) . . ? C65 C64 N63 111.0(4) . . ? C65 C64 H64A 124.5 . . ? N63 C64 H64A 124.5 . . ? C64 C65 N61 105.8(4) . . ? C64 C65 H65A 127.1 . . ? N61 C65 H65A 127.1 . . ? 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 C19 C11 C12 C13 -0.3(6) . . . . ? C21 C11 C12 C13 -179.6(4) . . . . ? C11 C12 C13 C14 -1.3(6) . . . . ? C12 C13 C14 C20 1.1(6) . . . . ? C12 C13 C14 C26 179.5(4) . . . . ? C20 C15 C16 C17 -1.0(6) . . . . ? C29 C15 C16 C17 179.8(4) . . . . ? C15 C16 C17 C18 -0.8(6) . . . . ? C16 C17 C18 C19 0.8(6) . . . . ? C16 C17 C18 C24 -179.4(4) . . . . ? C17 C18 C19 C20 1.0(6) . . . . ? C24 C18 C19 C20 -178.9(4) . . . . ? C17 C18 C19 C11 178.1(4) . . . . ? C24 C18 C19 C11 -1.7(6) . . . . ? C12 C11 C19 C20 2.0(6) . . . . ? C21 C11 C19 C20 -178.6(4) . . . . ? C12 C11 C19 C18 -175.1(4) . . . . ? C21 C11 C19 C18 4.3(6) . . . . ? C16 C15 C20 C19 2.8(6) . . . . ? C29 C15 C20 C19 -178.0(4) . . . . ? C16 C15 C20 C14 -174.9(4) . . . . ? C29 C15 C20 C14 4.3(6) . . . . ? C18 C19 C20 C15 -2.8(6) . . . . ? C11 C19 C20 C15 -179.9(4) . . . . ? C18 C19 C20 C14 174.9(4) . . . . ? C11 C19 C20 C14 -2.2(6) . . . . ? C13 C14 C20 C15 178.3(4) . . . . ? C26 C14 C20 C15 -0.1(6) . . . . ? C13 C14 C20 C19 0.7(6) . . . . ? C26 C14 C20 C19 -177.8(4) . . . . ? C12 C11 C21 O22 -1.4(6) . . . . ? C19 C11 C21 O22 179.3(4) . . . . ? C12 C11 C21 N23 178.8(4) . . . . ? C19 C11 C21 N23 -0.5(6) . . . . ? O22 C21 N23 C24 173.9(4) . . . . ? C11 C21 N23 C24 -6.3(6) . . . . ? O22 C21 N23 C31 0.9(6) . . . . ? C11 C21 N23 C31 -179.3(3) . . . . ? C21 N23 C24 O25 -170.5(4) . . . . ? C31 N23 C24 O25 2.7(6) . . . . ? C21 N23 C24 C18 8.7(6) . . . . ? C31 N23 C24 C18 -178.1(3) . . . . ? C17 C18 C24 O25 -5.1(6) . . . . ? C19 C18 C24 O25 174.8(4) . . . . ? C17 C18 C24 N23 175.8(4) . . . . ? C19 C18 C24 N23 -4.4(6) . . . . ? C13 C14 C26 O27 -3.4(6) . . . . ? C20 C14 C26 O27 175.0(4) . . . . ? C13 C14 C26 N28 179.2(4) . . . . ? C20 C14 C26 N28 -2.4(6) . . . . ? O27 C26 N28 C29 -176.8(4) . . . . ? C14 C26 N28 C29 0.7(6) . . . . ? O27 C26 N28 C51 0.3(6) . . . . ? C14 C26 N28 C51 177.7(4) . . . . ? C26 N28 C29 O30 -178.8(4) . . . . ? C51 N28 C29 O30 4.1(6) . . . . ? C26 N28 C29 C15 3.3(6) . . . . ? C51 N28 C29 C15 -173.7(4) . . . . ? C16 C15 C29 O30 -4.5(6) . . . . ? C20 C15 C29 O30 176.4(4) . . . . ? C16 C15 C29 N28 173.3(4) . . . . ? C20 C15 C29 N28 -5.8(6) . . . . ? C21 N23 C31 C32 90.6(4) . . . . ? C24 N23 C31 C32 -83.1(4) . . . . ? N23 C31 C32 C33 174.0(3) . . . . ? C31 C32 C33 N41 -59.8(5) . . . . ? C32 C33 N41 C42 -64.9(5) . . . . ? C32 C33 N41 C45 116.3(4) . . . . ? C45 N41 C42 N43 0.8(5) . . . . ? C33 N41 C42 N43 -178.2(4) . . . . ? N41 C42 N43 C44 -0.8(5) . . . . ? C42 N43 C44 C45 0.4(5) . . . . ? N43 C44 C45 N41 0.0(5) . . . . ? C42 N41 C45 C44 -0.5(5) . . . . ? C33 N41 C45 C44 178.5(4) . . . . ? C29 N28 C51 C52 -81.9(4) . . . . ? C26 N28 C51 C52 100.8(4) . . . . ? N28 C51 C52 C53 -76.4(5) . . . . ? C51 C52 C53 N61 -70.1(4) . . . . ? C52 C53 N61 C62 109.0(4) . . . . ? C52 C53 N61 C65 -74.2(5) . . . . ? C65 N61 C62 N63 -0.3(5) . . . . ? C53 N61 C62 N63 177.0(3) . . . . ? N61 C62 N63 C64 0.2(5) . . . . ? C62 N63 C64 C65 -0.1(5) . . . . ? N63 C64 C65 N61 -0.1(5) . . . . ? C62 N61 C65 C64 0.2(4) . . . . ? C53 N61 C65 C64 -177.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.29 _refine_diff_density_min -0.27 _refine_diff_density_rms 0.07 _database_code_depnum_ccdc_archive 'CCDC 942763' ####################################################################### # # 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_mnvrln _nottingham_internal_coll_name MNVRLN _nottingham_internal_coll_number 10877 _nottingham_internal_coll_client VJR/NRC _nottingham_internal_coll_type custom _nottingham_internal_coll_frame_time 12s _nottingham_internal_coll_frame_width '0.3 degrees' _nottingham_internal_coll_frame_method \w _nottingham_internal_coll_user 'Peter N. Horton @ NCS' _nottingham_internal_coll_date 27/11/2011 _nottingham_internal_process_user 'Peter N. Horton @ NCS' _nottingham_internal_process_date 28/11/2011 _nottingham_internal_solution_user VJR _nottingham_internal_solution_date 30/11/2011 _nottingham_internal_refinement_user VJR _nottingham_internal_refinement_date 30/11/2011 _nottingham_internal_validation_user AJB _nottingham_internal_validation_date 31/1/2012 _nottingham_internal_archive_date ? # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.500 0.500 46 14 'C H4 O ' _platon_squeeze_details ; ; _refine_special_details ; PLATON SQUEEZE (see above) has been applied to the data to remove the scattering contributions from a region of diffuse solvent which could not be modelled as discrete atoms. A set of solvent-free diffraction intensities was produced and this was used for the final cycles of refinement. 14 electrons were removed from a void spanning the inversion centre; this corresponds to half a molecule of methanol per asymmetric unit and has been included in the formula sum. ; _audit_creation_date 2012-01-27 _audit_creation_method ; Olex2 1.1 (compiled Nov 1 2011 20:42:30, GUI svn.r3906) ; _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C78 H66 Mn N18 O12, 2(N O3), (C H4 O)' _chemical_formula_sum 'C79 H70 Mn N20 O19' _chemical_formula_weight 1658.49 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.959(10) _cell_length_b 12.244(10) _cell_length_c 14.385(17) _cell_angle_alpha 87.42(5) _cell_angle_beta 88.82(5) _cell_angle_gamma 68.55(5) _cell_volume 1795(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4068 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 31.2 _exptl_crystal_description rhombus _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method ? _exptl_crystal_F_000 861 _exptl_absorpt_coefficient_mu 0.278 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.973 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_source_power 2.5 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type 'Mo K\a' _diffrn_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_specimen_support Mitegen _diffrn_detector CCD _diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle' _diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_reflns_av_R_equivalents 0.075 _diffrn_reflns_av_unetI/netI 0.119 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 14007 _diffrn_reflns_theta_full 25.10 _diffrn_reflns_theta_max 25.10 _diffrn_reflns_theta_min 2.45 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_gt 3800 _reflns_number_total 6369 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.33 _refine_diff_density_min -0.36 _refine_diff_density_rms 0.07 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 529 _refine_ls_number_reflns 6369 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.164 _refine_ls_R_factor_gt 0.0977 _refine_ls_restrained_S_all 1.12 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.084P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.207 _refine_ls_wR_factor_ref 0.241 _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 C11A C 1.6496(5) 0.5906(5) -0.1177(4) 0.0427(14) Uani 1 1 d . . . C11B C 1.1207(7) 0.5601(5) -0.0549(5) 0.0579(17) Uani 1 1 d . . . C12A C 1.5690(5) 0.6231(5) -0.0407(4) 0.0439(14) Uani 1 1 d . . . H12A H 1.5163 0.5792 -0.0220 0.053 Uiso 1 1 calc R . . C12B C 1.0993(7) 0.6578(5) -0.0043(5) 0.0571(18) Uani 1 1 d . . . H12B H 1.1468 0.7076 -0.0187 0.068 Uiso 1 1 calc R . . C13A C 1.5635(5) 0.7199(5) 0.0103(4) 0.0413(13) Uani 1 1 d . . . H13A H 1.5087 0.7398 0.0637 0.050 Uiso 1 1 calc R . . C14A C 1.6375(5) 0.7865(5) -0.0167(4) 0.0391(13) Uani 1 1 d . . . C15A C 1.7957(5) 0.8235(5) -0.1262(4) 0.0368(13) Uani 1 1 d . . . C16A C 1.8682(5) 0.7964(5) -0.2067(4) 0.0458(14) Uani 1 1 d . . . H16A H 1.9180 0.8424 -0.2269 0.055 Uiso 1 1 calc R . . C17A C 1.8703(5) 0.7019(5) -0.2597(4) 0.0434(14) Uani 1 1 d . . . H17A H 1.9205 0.6853 -0.3154 0.052 Uiso 1 1 calc R . . C17B C 0.9915(7) 0.3158(5) -0.0678(5) 0.0604(19) Uani 1 1 d . . . H17B H 1.0048 0.2483 -0.1027 0.072 Uiso 1 1 calc R . . C18A C 1.8001(5) 0.6335(4) -0.2311(4) 0.0380(13) Uani 1 1 d . . . C18B C 1.0638(6) 0.3871(5) -0.0900(5) 0.0560(18) Uani 1 1 d . . . C19A C 1.7225(5) 0.6597(5) -0.1487(4) 0.0371(13) Uani 1 1 d . . . C19B C 1.0477(6) 0.4875(5) -0.0383(4) 0.063(2) Uani 1 1 d . . . C20A C 1.7185(5) 0.7576(5) -0.0967(4) 0.0405(14) Uani 1 1 d . . . C21A C 1.6601(5) 0.4848(5) -0.1683(4) 0.0445(15) Uani 1 1 d . . . C21B C 1.2232(7) 0.5260(5) -0.1291(5) 0.065(2) Uani 1 1 d . . . C24A C 1.8033(5) 0.5337(5) -0.2862(4) 0.0441(14) Uani 1 1 d . . . C24B C 1.1617(7) 0.3571(5) -0.1665(5) 0.0589(18) Uani 1 1 d . . . C26A C 1.6306(5) 0.8892(5) 0.0366(4) 0.0439(14) Uani 1 1 d . . . C29A C 1.7989(5) 0.9205(5) -0.0699(4) 0.0421(14) Uani 1 1 d . . . C31A C 1.7412(5) 0.3604(5) -0.3043(4) 0.0446(14) Uani 1 1 d . . . H31A H 1.7565 0.3745 -0.3711 0.053 Uiso 1 1 calc R . . H31B H 1.6577 0.3466 -0.2985 0.053 Uiso 1 1 calc R . . C31B C 1.3437(7) 0.3922(6) -0.2501(5) 0.069(2) Uani 1 1 d . . . H31C H 1.3649 0.3087 -0.2637 0.082 Uiso 1 1 calc R . . H31D H 1.4227 0.3993 -0.2231 0.082 Uiso 1 1 calc R . . C32A C 1.8529(6) 0.2528(5) -0.2668(4) 0.0560(17) Uani 1 1 d . . . H32A H 1.9340 0.2706 -0.2659 0.067 Uiso 1 1 calc R . . H32B H 1.8325 0.2344 -0.2020 0.067 Uiso 1 1 calc R . . C32B C 1.3091(7) 0.4668(6) -0.3412(5) 0.070(2) Uani 1 1 d . . . H32C H 1.2912 0.5496 -0.3271 0.084 Uiso 1 1 calc R . . H32D H 1.3864 0.4410 -0.3830 0.084 Uiso 1 1 calc R . . C33A C 1.8767(6) 0.1462(5) -0.3247(5) 0.0595(18) Uani 1 1 d . . . H33A H 1.9056 0.1620 -0.3878 0.071 Uiso 1 1 calc R . . H33B H 1.9483 0.0784 -0.2962 0.071 Uiso 1 1 calc R . . C33B C 1.1911(7) 0.4611(5) -0.3932(4) 0.0644(19) Uani 1 1 d . . . H33C H 1.1148 0.4812 -0.3505 0.077 Uiso 1 1 calc R . . H33D H 1.1687 0.5203 -0.4455 0.077 Uiso 1 1 calc R . . C42A C 1.7159(6) 0.0886(5) -0.4121(4) 0.0478(15) Uani 1 1 d . . . H42A H 1.7552 0.0899 -0.4714 0.057 Uiso 1 1 calc R . . C42B C 1.3343(6) 0.2581(5) -0.4459(4) 0.0529(16) Uani 1 1 d . . . H42B H 1.4160 0.2650 -0.4335 0.064 Uiso 1 1 calc R . . C44A C 1.5873(6) 0.0716(5) -0.3031(4) 0.0524(16) Uani 1 1 d . . . H44A H 1.5177 0.0571 -0.2710 0.063 Uiso 1 1 calc R . . C44B C 1.1870(6) 0.1937(5) -0.4887(4) 0.0500(15) Uani 1 1 d . . . H44B H 1.1466 0.1443 -0.5126 0.060 Uiso 1 1 calc R . . C45A C 1.6773(7) 0.1066(5) -0.2635(5) 0.0594(18) Uani 1 1 d . . . H45A H 1.6819 0.1218 -0.1997 0.071 Uiso 1 1 calc R . . C45B C 1.1212(6) 0.3029(6) -0.4578(4) 0.0549(17) Uani 1 1 d . . . H45B H 1.0288 0.3431 -0.4558 0.066 Uiso 1 1 calc R . . C51A C 1.7149(5) 1.0460(5) 0.0644(4) 0.0461(14) Uani 1 1 d . . . H51A H 1.6295 1.0789 0.0969 0.055 Uiso 1 1 calc R . . H51B H 1.7246 1.1088 0.0225 0.055 Uiso 1 1 calc R . . C52A C 1.8252(5) 1.0071(5) 0.1360(4) 0.0399(13) Uani 1 1 d . . . H52A H 1.8240 0.9361 0.1713 0.048 Uiso 1 1 calc R . . H52B H 1.9106 0.9862 0.1033 0.048 Uiso 1 1 calc R . . C53A C 1.8117(5) 1.1028(5) 0.2035(4) 0.0445(14) Uani 1 1 d . . . H53A H 1.8927 1.0802 0.2409 0.053 Uiso 1 1 calc R . . H53B H 1.8019 1.1766 0.1677 0.053 Uiso 1 1 calc R . . C62A C 1.6820(6) 1.0451(5) 0.3298(4) 0.0471(15) Uani 1 1 d . . . H62A H 1.7417 0.9663 0.3375 0.057 Uiso 1 1 calc R . . C64A C 1.5192(6) 1.2052(6) 0.3455(4) 0.0570(17) Uani 1 1 d . . . H64A H 1.4398 1.2616 0.3673 0.068 Uiso 1 1 calc R . . C65A C 1.5938(6) 1.2259(6) 0.2778(4) 0.0596(18) Uani 1 1 d . . . H65A H 1.5771 1.2982 0.2437 0.072 Uiso 1 1 calc R . . N23A N 1.7314(4) 0.4655(4) -0.2518(3) 0.0435(12) Uani 1 1 d . . . N23B N 1.2355(5) 0.4282(4) -0.1809(4) 0.0603(15) Uani 1 1 d . . . N28A N 1.7157(4) 0.9476(4) 0.0083(3) 0.0415(11) Uani 1 1 d . . . N41A N 1.7597(5) 0.1156(4) -0.3324(4) 0.0524(14) Uani 1 1 d . . . N41B N 1.2164(5) 0.3437(4) -0.4299(4) 0.0570(14) Uani 1 1 d . . . N43A N 1.6122(4) 0.0604(4) -0.3972(3) 0.0481(13) Uani 1 1 d . . . N43B N 1.3229(4) 0.1638(4) -0.4806(3) 0.0439(11) Uani 1 1 d . . . N61A N 1.6988(4) 1.1239(4) 0.2663(3) 0.0411(11) Uani 1 1 d . . . N63A N 1.5737(4) 1.0896(4) 0.3797(3) 0.0425(12) Uani 1 1 d . . . O22A O 1.6133(4) 0.4128(3) -0.1378(3) 0.0549(11) Uani 1 1 d . . . O22B O 1.2949(5) 0.5818(4) -0.1444(3) 0.0676(13) Uani 1 1 d . . . O25A O 1.8679(4) 0.5069(4) -0.3576(3) 0.0535(11) Uani 1 1 d . . . O25B O 1.1782(4) 0.2739(4) -0.2149(3) 0.0684(13) Uani 1 1 d . . . O27A O 1.5546(4) 0.9227(3) 0.1019(3) 0.0487(10) Uani 1 1 d . . . O30A O 1.8694(3) 0.9764(3) -0.0873(3) 0.0456(10) Uani 1 1 d . . . Mn1 Mn 1.5000 0.0000 -0.5000 0.0422(4) Uani 1 2 d S . . N1C N 0.8790(5) 0.2166(5) 0.4078(4) 0.0570(14) Uani 1 1 d . . . O2C O 0.8873(5) 0.2656(5) 0.3316(4) 0.0913(18) Uani 1 1 d . . . O3C O 0.9247(5) 0.1086(4) 0.4189(4) 0.0902(18) Uani 1 1 d . . . O4C O 0.8199(5) 0.2806(4) 0.4735(3) 0.0756(14) 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 C11A 0.047(3) 0.036(3) 0.054(4) 0.009(3) -0.017(3) -0.025(3) C11B 0.066(4) 0.042(4) 0.065(4) -0.001(3) -0.026(4) -0.017(4) C12A 0.045(3) 0.039(4) 0.055(4) 0.007(3) -0.008(3) -0.024(3) C12B 0.076(5) 0.031(4) 0.063(4) -0.003(3) -0.032(4) -0.017(3) C13A 0.045(3) 0.038(3) 0.045(3) 0.005(3) -0.001(3) -0.022(3) C14A 0.040(3) 0.037(3) 0.042(3) 0.003(3) -0.009(3) -0.016(3) C15A 0.036(3) 0.036(3) 0.042(3) -0.002(2) -0.003(2) -0.017(3) C16A 0.047(3) 0.041(4) 0.056(4) -0.001(3) -0.009(3) -0.024(3) C17A 0.050(3) 0.038(3) 0.046(3) -0.004(3) 0.000(3) -0.021(3) C17B 0.079(5) 0.035(4) 0.069(5) 0.001(3) -0.033(4) -0.023(4) C18A 0.039(3) 0.030(3) 0.050(3) 0.005(2) -0.010(3) -0.019(3) C18B 0.060(4) 0.032(4) 0.068(4) -0.003(3) -0.038(4) -0.006(3) C19A 0.037(3) 0.032(3) 0.047(3) 0.005(2) -0.010(3) -0.018(3) C19B 0.079(5) 0.032(3) 0.076(5) 0.003(4) -0.051(4) -0.017(4) C20A 0.041(3) 0.033(3) 0.048(3) 0.009(3) -0.015(3) -0.015(3) C21A 0.049(3) 0.042(4) 0.054(4) 0.007(3) -0.020(3) -0.031(3) C21B 0.086(5) 0.036(4) 0.075(5) 0.008(3) -0.046(4) -0.024(4) C24A 0.046(3) 0.037(3) 0.052(4) 0.003(3) -0.013(3) -0.019(3) C24B 0.070(4) 0.036(4) 0.075(5) -0.001(3) -0.037(4) -0.023(4) C26A 0.045(3) 0.036(3) 0.052(4) 0.006(3) -0.012(3) -0.016(3) C29A 0.038(3) 0.039(3) 0.049(4) -0.001(3) -0.010(3) -0.013(3) C31A 0.050(3) 0.037(3) 0.052(4) -0.004(3) -0.011(3) -0.021(3) C31B 0.073(5) 0.048(4) 0.083(5) -0.006(4) -0.032(4) -0.019(4) C32A 0.061(4) 0.040(4) 0.073(4) -0.009(3) -0.028(3) -0.024(3) C32B 0.094(5) 0.044(4) 0.078(5) 0.001(3) -0.032(4) -0.031(4) C33A 0.058(4) 0.046(4) 0.079(5) -0.004(3) -0.029(3) -0.023(3) C33B 0.089(5) 0.042(4) 0.064(4) -0.005(3) -0.032(4) -0.025(4) C42A 0.057(4) 0.034(3) 0.057(4) -0.002(3) -0.015(3) -0.022(3) C42B 0.058(4) 0.042(4) 0.059(4) -0.002(3) -0.013(3) -0.019(3) C44A 0.081(4) 0.043(4) 0.045(4) 0.005(3) -0.012(3) -0.037(4) C44B 0.061(4) 0.051(4) 0.045(4) 0.005(3) -0.017(3) -0.029(3) C45A 0.085(5) 0.051(4) 0.055(4) 0.017(3) -0.029(4) -0.041(4) C45B 0.059(4) 0.050(4) 0.061(4) 0.003(3) -0.020(3) -0.025(4) C51A 0.050(3) 0.036(3) 0.055(4) 0.000(3) -0.005(3) -0.018(3) C52A 0.038(3) 0.041(3) 0.046(3) -0.005(3) 0.000(2) -0.021(3) C53A 0.044(3) 0.041(4) 0.054(4) -0.001(3) 0.000(3) -0.023(3) C62A 0.057(4) 0.038(4) 0.053(4) 0.008(3) -0.004(3) -0.026(3) C64A 0.050(4) 0.061(4) 0.055(4) 0.022(3) 0.000(3) -0.016(3) C65A 0.051(4) 0.054(4) 0.068(4) 0.024(3) -0.008(3) -0.015(3) N23A 0.048(3) 0.036(3) 0.050(3) 0.002(2) -0.011(2) -0.020(2) N23B 0.074(4) 0.030(3) 0.077(4) -0.004(3) -0.030(3) -0.017(3) N28A 0.042(3) 0.036(3) 0.053(3) -0.001(2) -0.005(2) -0.022(2) N41A 0.060(3) 0.028(3) 0.072(4) 0.004(2) -0.031(3) -0.017(3) N41B 0.065(3) 0.042(3) 0.064(4) -0.004(3) -0.016(3) -0.018(3) N43A 0.055(3) 0.043(3) 0.056(3) 0.005(2) -0.016(2) -0.030(3) N43B 0.054(3) 0.034(3) 0.049(3) -0.004(2) -0.008(2) -0.021(2) N61A 0.042(3) 0.037(3) 0.049(3) 0.004(2) -0.008(2) -0.020(2) N63A 0.047(3) 0.046(3) 0.044(3) 0.002(2) -0.009(2) -0.028(3) O22A 0.068(3) 0.052(3) 0.063(3) 0.004(2) -0.007(2) -0.045(2) O22B 0.090(3) 0.048(3) 0.076(3) 0.002(2) -0.027(3) -0.037(3) O25A 0.068(3) 0.053(3) 0.050(3) -0.013(2) 0.003(2) -0.034(2) O25B 0.080(3) 0.039(3) 0.087(3) -0.015(2) -0.028(3) -0.020(2) O27A 0.054(2) 0.051(3) 0.048(3) 0.001(2) 0.001(2) -0.026(2) O30A 0.050(2) 0.046(2) 0.054(2) 0.0016(19) -0.0045(18) -0.033(2) Mn1 0.0517(7) 0.0401(8) 0.0438(7) -0.0008(6) -0.0078(6) -0.0272(6) N1C 0.048(3) 0.051(4) 0.075(4) -0.018(3) 0.000(3) -0.020(3) O2C 0.123(4) 0.083(4) 0.099(4) -0.036(3) 0.053(4) -0.075(4) O3C 0.101(4) 0.043(3) 0.109(4) -0.026(3) -0.036(3) -0.002(3) O4C 0.101(4) 0.055(3) 0.067(3) -0.011(3) 0.006(3) -0.024(3) _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 C11A C12A 1.380(8) . ? C11A C19A 1.413(7) . ? C11A C21A 1.482(7) . ? C11B C12B 1.372(8) . ? C11B C19B 1.408(9) . ? C11B C21B 1.490(10) . ? C12A H12A 0.9500 . ? C12A C13A 1.405(7) . ? C12B H12B 0.9500 . ? C12B C17B 1.386(9) 2_765 ? C13A H13A 0.9500 . ? C13A C14A 1.384(7) . ? C14A C20A 1.415(8) . ? C14A C26A 1.479(7) . ? C15A C16A 1.372(7) . ? C15A C20A 1.415(7) . ? C15A C29A 1.479(7) . ? C16A H16A 0.9500 . ? C16A C17A 1.407(7) . ? C17A H17A 0.9500 . ? C17A C18A 1.375(7) . ? C17B C12B 1.386(9) 2_765 ? C17B H17B 0.9500 . ? C17B C18B 1.401(9) . ? C18A C19A 1.423(8) . ? C18A C24A 1.476(7) . ? C18B C19B 1.420(8) . ? C18B C24B 1.482(9) . ? C19A C20A 1.428(7) . ? C19B C19B 1.465(14) 2_765 ? C21A N23A 1.400(7) . ? C21A O22A 1.232(6) . ? C21B N23B 1.402(8) . ? C21B O22B 1.227(7) . ? C24A N23A 1.411(7) . ? C24A O25A 1.223(7) . ? C24B N23B 1.394(8) . ? C24B O25B 1.217(7) . ? C26A N28A 1.412(7) . ? C26A O27A 1.224(7) . ? C29A N28A 1.407(7) . ? C29A O30A 1.220(6) . ? C31A H31A 0.9900 . ? C31A H31B 0.9900 . ? C31A C32A 1.520(8) . ? C31A N23A 1.490(6) . ? C31B H31C 0.9900 . ? C31B H31D 0.9900 . ? C31B C32B 1.535(9) . ? C31B N23B 1.483(9) . ? C32A H32A 0.9900 . ? C32A H32B 0.9900 . ? C32A C33A 1.518(8) . ? C32B H32C 0.9900 . ? C32B H32D 0.9900 . ? C32B C33B 1.532(8) . ? C33A H33A 0.9900 . ? C33A H33B 0.9900 . ? C33A N41A 1.469(7) . ? C33B H33C 0.9900 . ? C33B H33D 0.9900 . ? C33B N41B 1.480(7) . ? C42A H42A 0.9500 . ? C42A N41A 1.352(7) . ? C42A N43A 1.315(7) . ? C42B H42B 0.9500 . ? C42B N41B 1.356(7) . ? C42B N43B 1.327(7) . ? C44A H44A 0.9500 . ? C44A C45A 1.355(7) . ? C44A N43A 1.378(7) . ? C44B H44B 0.9500 . ? C44B C45B 1.356(8) . ? C44B N43B 1.404(7) . ? C45A H45A 0.9500 . ? C45A N41A 1.354(8) . ? C45B H45B 0.9500 . ? C45B N41B 1.385(7) . ? C51A H51A 0.9900 . ? C51A H51B 0.9900 . ? C51A C52A 1.529(7) . ? C51A N28A 1.477(6) . ? C52A H52A 0.9900 . ? C52A H52B 0.9900 . ? C52A C53A 1.519(7) . ? C53A H53A 0.9900 . ? C53A H53B 0.9900 . ? C53A N61A 1.468(7) . ? C62A H62A 0.9500 . ? C62A N61A 1.357(7) . ? C62A N63A 1.322(7) . ? C64A H64A 0.9500 . ? C64A C65A 1.333(8) . ? C64A N63A 1.390(7) . ? C65A H65A 0.9500 . ? C65A N61A 1.367(7) . ? N43A Mn1 2.255(5) . ? N43B Mn1 2.246(5) . ? N63A Mn1 2.296(5) 1_566 ? Mn1 N43A 2.255(5) 2_854 ? Mn1 N43B 2.246(5) 2_854 ? Mn1 N63A 2.296(5) 1_544 ? Mn1 N63A 2.296(5) 2_865 ? N1C O2C 1.244(7) . ? N1C O3C 1.236(7) . ? N1C O4C 1.264(7) . ? 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 C12A C11A C19A 119.5(5) . . ? C12A C11A C21A 120.8(5) . . ? C19A C11A C21A 119.7(6) . . ? C12B C11B C19B 121.3(7) . . ? C12B C11B C21B 121.3(6) . . ? C19B C11B C21B 117.4(6) . . ? C11A C12A H12A 119.5 . . ? C11A C12A C13A 121.1(5) . . ? C13A C12A H12A 119.5 . . ? C11B C12B H12B 119.8 . . ? C11B C12B C17B 120.3(7) . 2_765 ? C17B C12B H12B 119.8 2_765 . ? C12A C13A H13A 119.7 . . ? C14A C13A C12A 120.5(5) . . ? C14A C13A H13A 119.7 . . ? C13A C14A C20A 119.9(5) . . ? C13A C14A C26A 120.4(5) . . ? C20A C14A C26A 119.7(5) . . ? C16A C15A C20A 119.8(5) . . ? C16A C15A C29A 120.3(5) . . ? C20A C15A C29A 119.9(5) . . ? C15A C16A H16A 119.3 . . ? C15A C16A C17A 121.3(5) . . ? C17A C16A H16A 119.3 . . ? C16A C17A H17A 119.8 . . ? C18A C17A C16A 120.3(6) . . ? C18A C17A H17A 119.8 . . ? C12B C17B H17B 119.5 2_765 . ? C12B C17B C18B 121.1(6) 2_765 . ? C18B C17B H17B 119.5 . . ? C17A C18A C19A 120.0(5) . . ? C17A C18A C24A 120.4(5) . . ? C19A C18A C24A 119.7(5) . . ? C17B C18B C19B 120.9(7) . . ? C17B C18B C24B 120.6(6) . . ? C19B C18B C24B 118.5(6) . . ? C11A C19A C18A 121.2(5) . . ? C11A C19A C20A 119.6(5) . . ? C18A C19A C20A 119.2(4) . . ? C11B C19B C18B 123.6(7) . . ? C11B C19B C19B 119.5(7) . 2_765 ? C18B C19B C19B 116.9(7) . 2_765 ? C14A C20A C19A 119.3(5) . . ? C15A C20A C14A 121.4(5) . . ? C15A C20A C19A 119.3(5) . . ? N23A C21A C11A 117.3(5) . . ? O22A C21A C11A 122.5(6) . . ? O22A C21A N23A 120.1(5) . . ? N23B C21B C11B 118.1(6) . . ? O22B C21B C11B 121.0(6) . . ? O22B C21B N23B 120.8(8) . . ? N23A C24A C18A 117.4(5) . . ? O25A C24A C18A 122.7(5) . . ? O25A C24A N23A 120.0(5) . . ? N23B C24B C18B 117.3(6) . . ? O25B C24B C18B 121.8(6) . . ? O25B C24B N23B 120.9(7) . . ? N28A C26A C14A 116.8(5) . . ? O27A C26A C14A 122.0(5) . . ? O27A C26A N28A 121.2(5) . . ? N28A C29A C15A 116.8(5) . . ? O30A C29A C15A 123.9(5) . . ? O30A C29A N28A 119.3(5) . . ? H31A C31A H31B 108.1 . . ? C32A C31A H31A 109.6 . . ? C32A C31A H31B 109.6 . . ? N23A C31A H31A 109.6 . . ? N23A C31A H31B 109.6 . . ? N23A C31A C32A 110.3(4) . . ? H31C C31B H31D 107.8 . . ? C32B C31B H31C 109.1 . . ? C32B C31B H31D 109.1 . . ? N23B C31B H31C 109.1 . . ? N23B C31B H31D 109.1 . . ? N23B C31B C32B 112.5(6) . . ? C31A C32A H32A 109.1 . . ? C31A C32A H32B 109.1 . . ? H32A C32A H32B 107.9 . . ? C33A C32A C31A 112.4(5) . . ? C33A C32A H32A 109.1 . . ? C33A C32A H32B 109.1 . . ? C31B C32B H32C 108.5 . . ? C31B C32B H32D 108.5 . . ? H32C C32B H32D 107.5 . . ? C33B C32B C31B 115.2(6) . . ? C33B C32B H32C 108.5 . . ? C33B C32B H32D 108.5 . . ? C32A C33A H33A 109.0 . . ? C32A C33A H33B 109.0 . . ? H33A C33A H33B 107.8 . . ? N41A C33A C32A 112.9(5) . . ? N41A C33A H33A 109.0 . . ? N41A C33A H33B 109.0 . . ? C32B C33B H33C 109.1 . . ? C32B C33B H33D 109.1 . . ? H33C C33B H33D 107.8 . . ? N41B C33B C32B 112.5(5) . . ? N41B C33B H33C 109.1 . . ? N41B C33B H33D 109.1 . . ? N41A C42A H42A 124.3 . . ? N43A C42A H42A 124.3 . . ? N43A C42A N41A 111.5(6) . . ? N41B C42B H42B 123.7 . . ? N43B C42B H42B 123.7 . . ? N43B C42B N41B 112.5(5) . . ? C45A C44A H44A 125.3 . . ? C45A C44A N43A 109.5(6) . . ? N43A C44A H44A 125.3 . . ? C45B C44B H44B 124.6 . . ? C45B C44B N43B 110.8(5) . . ? N43B C44B H44B 124.6 . . ? C44A C45A H45A 126.6 . . ? N41A C45A C44A 106.7(6) . . ? N41A C45A H45A 126.6 . . ? C44B C45B H45B 127.1 . . ? C44B C45B N41B 105.8(6) . . ? N41B C45B H45B 127.1 . . ? H51A C51A H51B 107.9 . . ? C52A C51A H51A 109.3 . . ? C52A C51A H51B 109.3 . . ? N28A C51A H51A 109.3 . . ? N28A C51A H51B 109.3 . . ? N28A C51A C52A 111.8(4) . . ? C51A C52A H52A 109.3 . . ? C51A C52A H52B 109.3 . . ? H52A C52A H52B 107.9 . . ? C53A C52A C51A 111.8(5) . . ? C53A C52A H52A 109.3 . . ? C53A C52A H52B 109.3 . . ? C52A C53A H53A 109.1 . . ? C52A C53A H53B 109.1 . . ? H53A C53A H53B 107.8 . . ? N61A C53A C52A 112.4(4) . . ? N61A C53A H53A 109.1 . . ? N61A C53A H53B 109.1 . . ? N61A C62A H62A 123.6 . . ? N63A C62A H62A 123.6 . . ? N63A C62A N61A 112.8(5) . . ? C65A C64A H64A 124.7 . . ? C65A C64A N63A 110.7(6) . . ? N63A C64A H64A 124.7 . . ? C64A C65A H65A 126.3 . . ? C64A C65A N61A 107.4(5) . . ? N61A C65A H65A 126.3 . . ? C21A N23A C24A 124.4(5) . . ? C21A N23A C31A 118.0(4) . . ? C24A N23A C31A 117.3(5) . . ? C21B N23B C31B 116.7(6) . . ? C24B N23B C21B 125.0(7) . . ? C24B N23B C31B 118.0(6) . . ? C26A N28A C51A 117.2(5) . . ? C29A N28A C26A 124.9(5) . . ? C29A N28A C51A 117.8(4) . . ? C42A N41A C33A 125.0(6) . . ? C42A N41A C45A 107.1(5) . . ? C45A N41A C33A 128.0(5) . . ? C42B N41B C33B 127.6(5) . . ? C42B N41B C45B 107.0(5) . . ? C45B N41B C33B 125.3(6) . . ? C42A N43A C44A 105.3(5) . . ? C42A N43A Mn1 128.5(4) . . ? C44A N43A Mn1 126.2(4) . . ? C42B N43B C44B 103.9(5) . . ? C42B N43B Mn1 120.8(4) . . ? C44B N43B Mn1 135.0(4) . . ? C62A N61A C53A 125.9(5) . . ? C62A N61A C65A 105.6(5) . . ? C65A N61A C53A 128.4(5) . . ? C62A N63A C64A 103.5(5) . . ? C62A N63A Mn1 128.1(4) . 1_566 ? C64A N63A Mn1 128.3(4) . 1_566 ? N43A Mn1 N43A 180.000(1) . 2_854 ? N43A Mn1 N63A 89.50(17) 2_854 1_544 ? N43A Mn1 N63A 90.50(17) . 1_544 ? N43A Mn1 N63A 89.50(17) . 2_865 ? N43A Mn1 N63A 90.50(17) 2_854 2_865 ? N43B Mn1 N43A 89.74(18) 2_854 . ? N43B Mn1 N43A 90.26(18) . . ? N43B Mn1 N43A 89.74(18) . 2_854 ? N43B Mn1 N43A 90.26(18) 2_854 2_854 ? N43B Mn1 N43B 180.0(2) 2_854 . ? N43B Mn1 N63A 91.18(18) . 1_544 ? N43B Mn1 N63A 91.18(18) 2_854 2_865 ? N43B Mn1 N63A 88.82(18) . 2_865 ? N43B Mn1 N63A 88.82(18) 2_854 1_544 ? N63A Mn1 N63A 180.000(1) 2_865 1_544 ? O2C N1C O4C 118.0(6) . . ? O3C N1C O2C 121.2(6) . . ? O3C N1C O4C 120.7(6) . . ? 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 C11A C12A C13A C14A 1.2(8) . . . . ? C11A C19A C20A C14A -2.4(7) . . . . ? C11A C19A C20A C15A 177.6(5) . . . . ? C11A C21A N23A C24A 6.1(7) . . . . ? C11A C21A N23A C31A -179.1(4) . . . . ? C11B C21B N23B C24B -2.2(8) . . . . ? C11B C21B N23B C31B -176.3(5) . . . . ? C12A C11A C19A C18A -175.9(5) . . . . ? C12A C11A C19A C20A 4.1(8) . . . . ? C12A C11A C21A N23A 172.6(5) . . . . ? C12A C11A C21A O22A -10.3(8) . . . . ? C12A C13A C14A C20A 0.5(8) . . . . ? C12A C13A C14A C26A 179.3(5) . . . . ? C12B C11B C19B C18B 178.5(5) . . . . ? C12B C11B C19B C19B -3.7(10) . . . 2_765 ? C12B C11B C21B N23B -177.1(5) . . . . ? C12B C11B C21B O22B 3.0(9) . . . . ? C12B C17B C18B C19B 1.0(9) 2_765 . . . ? C12B C17B C18B C24B 179.2(5) 2_765 . . . ? C13A C14A C20A C15A -179.9(5) . . . . ? C13A C14A C20A C19A 0.1(7) . . . . ? C13A C14A C26A N28A 175.8(5) . . . . ? C13A C14A C26A O27A -4.4(8) . . . . ? C14A C26A N28A C29A 4.7(7) . . . . ? C14A C26A N28A C51A -176.6(4) . . . . ? C15A C16A C17A C18A -0.7(8) . . . . ? C15A C29A N28A C26A 0.1(7) . . . . ? C15A C29A N28A C51A -178.6(4) . . . . ? C16A C15A C20A C14A -176.9(5) . . . . ? C16A C15A C20A C19A 3.2(7) . . . . ? C16A C15A C29A N28A 176.1(5) . . . . ? C16A C15A C29A O30A -4.4(8) . . . . ? C16A C17A C18A C19A 1.4(8) . . . . ? C16A C17A C18A C24A -179.4(5) . . . . ? C17A C18A C19A C11A -179.8(5) . . . . ? C17A C18A C19A C20A 0.1(7) . . . . ? C17A C18A C24A N23A 178.6(5) . . . . ? C17A C18A C24A O25A 0.8(8) . . . . ? C17B C18B C19B C11B 177.6(5) . . . . ? C17B C18B C19B C19B -0.2(9) . . . 2_765 ? C17B C18B C24B N23B -176.2(5) . . . . ? C17B C18B C24B O25B 3.5(9) . . . . ? C18A C19A C20A C14A 177.6(5) . . . . ? C18A C19A C20A C15A -2.4(7) . . . . ? C18A C24A N23A C21A -1.4(7) . . . . ? C18A C24A N23A C31A -176.3(4) . . . . ? C18B C24B N23B C21B -0.6(8) . . . . ? C18B C24B N23B C31B 173.5(5) . . . . ? C19A C11A C12A C13A -3.5(8) . . . . ? C19A C11A C21A N23A -7.1(7) . . . . ? C19A C11A C21A O22A 170.0(5) . . . . ? C19A C18A C24A N23A -2.3(7) . . . . ? C19A C18A C24A O25A 179.9(5) . . . . ? C19B C11B C12B C17B 3.0(9) . . . 2_765 ? C19B C11B C21B N23B 3.5(8) . . . . ? C19B C11B C21B O22B -176.4(5) . . . . ? C19B C18B C24B N23B 2.0(8) . . . . ? C19B C18B C24B O25B -178.2(5) . . . . ? C20A C14A C26A N28A -5.4(7) . . . . ? C20A C14A C26A O27A 174.4(5) . . . . ? C20A C15A C16A C17A -1.7(8) . . . . ? C20A C15A C29A N28A -4.4(7) . . . . ? C20A C15A C29A O30A 175.0(5) . . . . ? C21A C11A C12A C13A 176.8(5) . . . . ? C21A C11A C19A C18A 3.8(7) . . . . ? C21A C11A C19A C20A -176.2(4) . . . . ? C21B C11B C12B C17B -176.4(5) . . . 2_765 ? C21B C11B C19B C18B -2.1(9) . . . . ? C21B C11B C19B C19B 175.7(6) . . . 2_765 ? C24A C18A C19A C11A 1.0(7) . . . . ? C24A C18A C19A C20A -179.0(4) . . . . ? C24B C18B C19B C11B -0.6(8) . . . . ? C24B C18B C19B C19B -178.5(6) . . . 2_765 ? C26A C14A C20A C15A 1.3(7) . . . . ? C26A C14A C20A C19A -178.7(4) . . . . ? C29A C15A C16A C17A 177.8(5) . . . . ? C29A C15A C20A C14A 3.7(7) . . . . ? C29A C15A C20A C19A -176.3(4) . . . . ? C31A C32A C33A N41A -57.0(7) . . . . ? C31B C32B C33B N41B -67.0(8) . . . . ? C32A C31A N23A C21A -84.6(6) . . . . ? C32A C31A N23A C24A 90.6(6) . . . . ? C32A C33A N41A C42A 134.4(6) . . . . ? C32A C33A N41A C45A -47.0(8) . . . . ? C32B C31B N23B C21B -80.8(6) . . . . ? C32B C31B N23B C24B 104.7(6) . . . . ? C32B C33B N41B C42B -20.3(9) . . . . ? C32B C33B N41B C45B 162.3(6) . . . . ? C42A N43A Mn1 N43B 65.0(5) . . . 2_854 ? C42A N43A Mn1 N43B -115.0(5) . . . . ? C42A N43A Mn1 N63A 156.2(5) . . . 2_865 ? C42A N43A Mn1 N63A -23.8(5) . . . 1_544 ? C42B N43B Mn1 N43A 19.9(4) . . . . ? C42B N43B Mn1 N43A -160.1(4) . . . 2_854 ? C42B N43B Mn1 N63A 109.4(4) . . . 2_865 ? C42B N43B Mn1 N63A -70.6(4) . . . 1_544 ? C44A C45A N41A C33A -177.5(5) . . . . ? C44A C45A N41A C42A 1.4(7) . . . . ? C44A N43A Mn1 N43B -112.7(5) . . . 2_854 ? C44A N43A Mn1 N43B 67.3(5) . . . . ? C44A N43A Mn1 N63A 158.5(5) . . . 1_544 ? C44A N43A Mn1 N63A -21.5(5) . . . 2_865 ? C44B C45B N41B C33B 178.3(5) . . . . ? C44B C45B N41B C42B 0.5(7) . . . . ? C44B N43B Mn1 N43A -152.7(5) . . . . ? C44B N43B Mn1 N43A 27.3(5) . . . 2_854 ? C44B N43B Mn1 N63A 116.8(5) . . . 1_544 ? C44B N43B Mn1 N63A -63.2(5) . . . 2_865 ? C45A C44A N43A C42A 0.0(7) . . . . ? C45A C44A N43A Mn1 178.1(4) . . . . ? C45B C44B N43B C42B -0.9(6) . . . . ? C45B C44B N43B Mn1 172.6(4) . . . . ? C51A C52A C53A N61A 69.1(6) . . . . ? C52A C51A N28A C26A 96.7(5) . . . . ? C52A C51A N28A C29A -84.5(6) . . . . ? C52A C53A N61A C62A 62.8(7) . . . . ? C52A C53A N61A C65A -121.2(6) . . . . ? C64A C65A N61A C53A -177.0(5) . . . . ? C64A C65A N61A C62A -0.3(7) . . . . ? C65A C64A N63A C62A 0.2(7) . . . . ? C65A C64A N63A Mn1 177.1(4) . . . 1_566 ? N23A C31A C32A C33A -173.7(5) . . . . ? N23B C31B C32B C33B -60.9(8) . . . . ? N28A C51A C52A C53A -171.0(4) . . . . ? N41A C42A N43A C44A 0.9(7) . . . . ? N41A C42A N43A Mn1 -177.2(3) . . . . ? N41B C42B N43B C44B 1.2(6) . . . . ? N41B C42B N43B Mn1 -173.4(4) . . . . ? N43A C42A N41A C33A 177.5(5) . . . . ? N43A C42A N41A C45A -1.5(7) . . . . ? N43A C44A C45A N41A -0.8(7) . . . . ? N43B C42B N41B C33B -178.9(5) . . . . ? N43B C42B N41B C45B -1.1(7) . . . . ? N43B C44B C45B N41B 0.2(7) . . . . ? N61A C62A N63A C64A -0.5(6) . . . . ? N61A C62A N63A Mn1 -177.3(3) . . . 1_566 ? N63A C62A N61A C53A 177.3(4) . . . . ? N63A C62A N61A C65A 0.5(6) . . . . ? N63A C64A C65A N61A 0.1(7) . . . . ? O22A C21A N23A C24A -171.2(5) . . . . ? O22A C21A N23A C31A 3.7(7) . . . . ? O22B C21B N23B C24B 177.7(5) . . . . ? O22B C21B N23B C31B 3.6(8) . . . . ? O25A C24A N23A C21A 176.4(5) . . . . ? O25A C24A N23A C31A 1.5(7) . . . . ? O25B C24B N23B C21B 179.7(5) . . . . ? O25B C24B N23B C31B -6.3(8) . . . . ? O27A C26A N28A C29A -175.1(5) . . . . ? O27A C26A N28A C51A 3.6(7) . . . . ? O30A C29A N28A C26A -179.4(5) . . . . ? O30A C29A N28A C51A 1.9(7) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 942764' ####################################################################### # # 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_mnvrla _nottingham_internal_coll_name MNVRLA _nottingham_internal_coll_number 9489 _nottingham_internal_coll_client VJR/NRC _nottingham_internal_coll_type custom _nottingham_internal_coll_frame_time 1.0 _nottingham_internal_coll_frame_width 0.5 _nottingham_internal_coll_frame_method omega _nottingham_internal_coll_user AJB _nottingham_internal_coll_date 01/07/2010 _nottingham_internal_process_user AJB _nottingham_internal_process_date 01/07/2010 _nottingham_internal_solution_user VJR/SPA _nottingham_internal_solution_date 08/07/2010 _nottingham_internal_refinement_user VJR/SPA _nottingham_internal_refinement_date 31/01/2012 _nottingham_internal_validation_user AJB _nottingham_internal_validation_date 12/2/2012 _nottingham_internal_archive_date ? _refine_special_details ; PLATON SQUEEZE (see below) has been applied to the data to remove the scattering contributions from regions of diffuse solvent which could not be modelled as discrete atoms. A set of solvent-free diffraction intensities was produced and this was used for the final cycles of refinement. A total of 292 electrons were removed from the P1 cell equating to two nitrate anions and four chloroform solvent molecules per formula unit;these have been included in the formula sum. ; # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.028 0.083 0.583 594 292 '(N O3)2,(C H Cl3)4' _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C78 H66 Mn N18 O12, (N O3)2 (C H Cl3)4' _chemical_formula_sum 'C82 H70 Cl12 Mn N20 O18' _chemical_formula_weight 2103.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Mn Mn 0.3400 0.6912 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0032 0.0015 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0108 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1418 0.1507 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.861(5) _cell_length_b 13.585(7) _cell_length_c 19.115(9) _cell_angle_alpha 97.849(4) _cell_angle_beta 94.829(6) _cell_angle_gamma 106.464(10) _cell_volume 2167.4(19) _cell_formula_units_Z 1 _cell_measurement_reflns_used 3730 _cell_measurement_temperature 110 _cell_measurement_theta_max 31.5 _cell_measurement_theta_min 1.7 _exptl_absorpt_coefficient_mu 0.217 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.578 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _exptl_crystal_colour yellow _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method ? _exptl_crystal_description prism _exptl_crystal_F_000 781 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.213 _diffrn_reflns_av_unetI/netI 0.178 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 17738 _diffrn_reflns_theta_full 24.84 _diffrn_reflns_theta_max 24.84 _diffrn_reflns_theta_min 1.54 _diffrn_ambient_temperature 110.0 _diffrn_detector CCD _diffrn_detector_area_resol_mean 28.5714 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measurement_details ; scan: Number of images: 206 Slice: -35.0000 - 68.0000 Image width: 0.5000 Exp time: 1.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -60.0000 Phi: 240.0000 XTD: 59.3661 2theta: 30.2337 scan: Number of images: 206 Slice: -35.0000 - 68.0000 Image width: 0.5000 Exp time: 1.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -60.0000 Phi: 0.0000 XTD: 59.3661 2theta: 30.2337 scan: Number of images: 206 Slice: -35.0000 - 68.0000 Image width: 0.5000 Exp time: 1.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -60.0000 Phi: 90.0000 XTD: 59.3661 2theta: 30.2337 scan: Number of images: 188 Slice: -35.0000 - 59.0000 Image width: 0.5000 Exp time: 1.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -60.0000 Phi: 180.0000 XTD: 59.3661 2theta: 30.2337 scan: Number of images: 78 Slice: -35.0000 - 4.0000 Image width: 0.5000 Exp time: 1.0000 Rotation axis: Omega Omega: 0.0000 Kappa: -60.0000 Phi: 120.0000 XTD: 59.3661 2theta: 30.2337 scan: Number of images: 76 Slice: -42.0000 - -4.0000 Image width: 0.5000 Exp time: 1.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 0.0000 Phi: 120.0000 XTD: 59.3661 2theta: 30.2337 scan: Number of images: 76 Slice: -32.0000 - 6.0000 Image width: 0.5000 Exp time: 1.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 0.0000 Phi: 0.0000 XTD: 59.3661 2theta: 30.2337 ; _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support MicroMount _diffrn_orient_matrix_type d*Trek _diffrn_orient_matrix_UB_11 0.117205 _diffrn_orient_matrix_UB_12 -0.017314 _diffrn_orient_matrix_UB_13 0.006978 _diffrn_orient_matrix_UB_21 0.013589 _diffrn_orient_matrix_UB_22 -0.041487 _diffrn_orient_matrix_UB_23 0.064474 _diffrn_orient_matrix_UB_31 0.000988 _diffrn_orient_matrix_UB_32 -0.048968 _diffrn_orient_matrix_UB_33 -0.020920 _diffrn_radiation_monochromator 'silicon double crystal' _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_source 'Diamond Light Source Beamline I19' _diffrn_source_current . _diffrn_source_power . _diffrn_source_voltage . _diffrn_special_details ; ? ; _reflns_number_gt 5875 _reflns_number_total 8111 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_data_collection ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _refine_diff_density_max 1.25 _refine_diff_density_min -0.77 _refine_diff_density_rms 0.12 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 493 _refine_ls_number_reflns 8111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.137 _refine_ls_R_factor_gt 0.119 _refine_ls_restrained_S_all 1.08 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.176P)^2^+3.944P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.338 _refine_ls_wR_factor_ref 0.355 _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 1.0000 0.5000 0.5000 0.0252(3) Uani 1 2 d S . . C11A C 0.7613(5) 0.2441(3) 0.9854(2) 0.0274(9) Uani 1 1 d . . . C12A C 0.8650(6) 0.2736(4) 1.0475(3) 0.0327(10) Uani 1 1 d . . . H12A H 0.9723 0.2744 1.0465 0.039 Uiso 1 1 calc R . . C13A C 0.8138(5) 0.3020(4) 1.1111(3) 0.0289(10) Uani 1 1 d . . . H13A H 0.8867 0.3220 1.1536 0.035 Uiso 1 1 calc R . . C14A C 0.6589(5) 0.3019(3) 1.1143(2) 0.0242(9) Uani 1 1 d . . . C15A C 0.3959(5) 0.2822(3) 1.0519(2) 0.0274(9) Uani 1 1 d . . . C16A C 0.2952(5) 0.2619(4) 0.9890(3) 0.0304(10) Uani 1 1 d . . . H16A H 0.1923 0.2701 0.9895 0.036 Uiso 1 1 calc R . . C17A C 0.3452(6) 0.2290(4) 0.9239(3) 0.0320(10) Uani 1 1 d . . . H17A H 0.2739 0.2115 0.8810 0.038 Uiso 1 1 calc R . . C18A C 0.4951(5) 0.2223(3) 0.9226(2) 0.0270(9) Uani 1 1 d . . . C19A C 0.6030(5) 0.2477(3) 0.9859(2) 0.0247(9) Uani 1 1 d . . . C20A C 0.5520(5) 0.2772(3) 1.0512(2) 0.0254(9) Uani 1 1 d . . . C21A C 0.8121(6) 0.2063(3) 0.9178(2) 0.0283(10) Uani 1 1 d . . . O22A O 0.9443(4) 0.1966(3) 0.91430(19) 0.0382(8) Uani 1 1 d . . . N23A N 0.6998(4) 0.1759(3) 0.8570(2) 0.0267(8) Uani 1 1 d . . . C24A C 0.5489(5) 0.1876(3) 0.8537(2) 0.0278(10) Uani 1 1 d . . . O25A O 0.4651(4) 0.1709(3) 0.79732(16) 0.0292(7) Uani 1 1 d . . . C26A C 0.6030(5) 0.3242(3) 1.1828(2) 0.0284(10) Uani 1 1 d . . . O27A O 0.6839(4) 0.3367(3) 1.23984(18) 0.0347(8) Uani 1 1 d . . . N28A N 0.4467(5) 0.3289(3) 1.1814(2) 0.0298(9) Uani 1 1 d . . . C29A C 0.3426(6) 0.3142(4) 1.1200(2) 0.0303(10) Uani 1 1 d . . . O30A O 0.2095(4) 0.3232(3) 1.12386(19) 0.0378(8) Uani 1 1 d . . . C31A C 0.7499(6) 0.1322(4) 0.7903(3) 0.0321(10) Uani 1 1 d . . . H31A H 0.6543 0.0888 0.7577 0.038 Uiso 1 1 calc R . . H31B H 0.8147 0.0866 0.8018 0.038 Uiso 1 1 calc R . . C32A C 0.8455(6) 0.2161(4) 0.7522(3) 0.0336(10) Uani 1 1 d . . . H32A H 0.9328 0.2654 0.7866 0.040 Uiso 1 1 calc R . . H32B H 0.8935 0.1831 0.7142 0.040 Uiso 1 1 calc R . . C33A C 0.7450(6) 0.2754(4) 0.7197(3) 0.0344(11) Uani 1 1 d . . . H33A H 0.6614 0.2271 0.6832 0.041 Uiso 1 1 calc R . . H33B H 0.6924 0.3056 0.7571 0.041 Uiso 1 1 calc R . . N41A N 0.8433(5) 0.3599(3) 0.6867(2) 0.0317(9) Uani 1 1 d . . . C42A C 0.8546(6) 0.3579(4) 0.6168(2) 0.0297(10) Uani 1 1 d . . . H42A H 0.8034 0.2997 0.5807 0.036 Uiso 1 1 calc R . . N43A N 0.9454(4) 0.4469(3) 0.6050(2) 0.0299(8) Uani 1 1 d . . . C44A C 0.9965(6) 0.5077(4) 0.6705(3) 0.0341(11) Uani 1 1 d . . . H44A H 1.0649 0.5772 0.6790 0.041 Uiso 1 1 calc R . . C45A C 0.9344(6) 0.4533(4) 0.7222(3) 0.0368(11) Uani 1 1 d . . . H45A H 0.9519 0.4765 0.7722 0.044 Uiso 1 1 calc R . . C51A C 0.3953(6) 0.3620(4) 1.2503(3) 0.0329(10) Uani 1 1 d . . . H51A H 0.4410 0.3321 1.2883 0.039 Uiso 1 1 calc R . . H51B H 0.2782 0.3362 1.2469 0.039 Uiso 1 1 calc R . . C52A C 0.4502(6) 0.4797(4) 1.2686(3) 0.0358(11) Uani 1 1 d . . . H52A H 0.3886 0.5083 1.2355 0.043 Uiso 1 1 calc R . . H52B H 0.5634 0.5056 1.2619 0.043 Uiso 1 1 calc R . . C53A C 0.4310(6) 0.5192(4) 1.3448(3) 0.0377(12) Uani 1 1 d . . . H53A H 0.4631 0.5962 1.3533 0.045 Uiso 1 1 calc R . . H53B H 0.3181 0.4935 1.3520 0.045 Uiso 1 1 calc R . . N61A N 0.5286(5) 0.4833(3) 1.3956(2) 0.0301(9) Uani 1 1 d . . . C62A C 0.6862(6) 0.5249(4) 1.4142(2) 0.0326(10) Uani 1 1 d . . . H62A H 0.7499 0.5822 1.3960 0.039 Uiso 1 1 calc R . . N63A N 0.7413(4) 0.4762(3) 1.4607(2) 0.0285(8) Uani 1 1 d . . . C64A C 0.6098(5) 0.3989(4) 1.4726(2) 0.0316(10) Uani 1 1 d . . . H64A H 0.6110 0.3501 1.5036 0.038 Uiso 1 1 calc R . . C65A C 0.4796(6) 0.4043(4) 1.4326(3) 0.0338(11) Uani 1 1 d . . . H65A H 0.3739 0.3610 1.4309 0.041 Uiso 1 1 calc R . . C11B C 1.0925(6) 0.0524(3) 0.0941(2) 0.0279(10) Uani 1 1 d . . . C12B C 1.2460(5) 0.0529(3) 0.0889(2) 0.0275(9) Uani 1 1 d . . . H12B H 1.3227 0.0756 0.1301 0.033 Uiso 1 1 calc R . . C17B C 0.7092(6) -0.0196(4) -0.0224(3) 0.0304(10) Uani 1 1 d . . . H17B H 0.6022 -0.0210 -0.0193 0.037 Uiso 1 1 calc R . . C18B C 0.8178(5) 0.0142(3) 0.0368(2) 0.0258(9) Uani 1 1 d . . . C19B C 0.9779(5) 0.0169(3) 0.0330(2) 0.0233(9) Uani 1 1 d . . . C31B C 0.8448(6) 0.1279(4) 0.2322(3) 0.0325(10) Uani 1 1 d . . . H31C H 0.7521 0.1534 0.2228 0.039 Uiso 1 1 calc R . . H31D H 0.9335 0.1874 0.2579 0.039 Uiso 1 1 calc R . . C32B C 0.8034(6) 0.0444(4) 0.2792(3) 0.0340(11) Uani 1 1 d . . . H32C H 0.7254 -0.0190 0.2512 0.041 Uiso 1 1 calc R . . H32D H 0.9002 0.0262 0.2944 0.041 Uiso 1 1 calc R . . C33B C 0.7348(7) 0.0804(4) 0.3444(3) 0.0390(12) Uani 1 1 d . . . H33C H 0.6392 0.1000 0.3292 0.047 Uiso 1 1 calc R . . H33D H 0.7018 0.0221 0.3713 0.047 Uiso 1 1 calc R . . C21B C 1.0475(6) 0.0892(3) 0.1638(2) 0.0278(10) Uani 1 1 d . . . O22B O 1.1409(4) 0.1198(3) 0.21705(18) 0.0372(8) Uani 1 1 d . . . N23B N 0.8898(5) 0.0892(3) 0.1645(2) 0.0265(8) Uani 1 1 d . . . C24B C 0.7697(5) 0.0494(3) 0.1063(2) 0.0276(10) Uani 1 1 d . . . O25B O 0.6335(4) 0.0441(3) 0.11357(19) 0.0343(8) Uani 1 1 d . . . N41B N 0.8487(5) 0.1693(3) 0.3912(2) 0.0317(9) Uani 1 1 d . . . C42B C 0.8352(6) 0.2658(4) 0.4054(3) 0.0320(10) Uani 1 1 d . . . H42B H 0.7488 0.2861 0.3857 0.038 Uiso 1 1 calc R . . N43B N 0.9575(5) 0.3297(3) 0.4504(2) 0.0302(9) Uani 1 1 d . . . C44B C 1.0524(6) 0.2682(4) 0.4640(3) 0.0373(11) Uani 1 1 d . . . H44B H 1.1507 0.2914 0.4942 0.045 Uiso 1 1 calc R . . C45B C 0.9860(7) 0.1700(5) 0.4281(3) 0.0445(13) Uani 1 1 d . . . H45B H 1.0277 0.1129 0.4287 0.053 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0261(5) 0.0301(6) 0.0196(5) 0.0034(4) 0.0048(4) 0.0083(4) C11A 0.035(2) 0.021(2) 0.028(2) 0.0076(17) 0.0014(18) 0.0099(18) C12A 0.026(2) 0.038(3) 0.034(3) 0.005(2) 0.0020(19) 0.013(2) C13A 0.028(2) 0.029(2) 0.028(2) 0.0036(18) -0.0018(18) 0.0081(18) C14A 0.027(2) 0.0181(19) 0.027(2) 0.0012(16) 0.0000(17) 0.0080(16) C15A 0.032(2) 0.024(2) 0.027(2) 0.0049(17) 0.0013(18) 0.0106(18) C16A 0.027(2) 0.035(2) 0.028(2) 0.0008(19) -0.0002(18) 0.0103(19) C17A 0.031(2) 0.036(3) 0.030(2) 0.0071(19) 0.0000(19) 0.010(2) C18A 0.030(2) 0.023(2) 0.030(2) 0.0082(17) 0.0073(18) 0.0086(17) C19A 0.026(2) 0.021(2) 0.028(2) 0.0071(17) 0.0014(17) 0.0086(17) C20A 0.029(2) 0.0177(19) 0.029(2) 0.0023(16) 0.0015(18) 0.0073(17) C21A 0.034(2) 0.025(2) 0.029(2) 0.0074(18) 0.0036(19) 0.0138(18) O22A 0.0364(19) 0.050(2) 0.0345(19) 0.0093(16) 0.0075(15) 0.0218(16) N23A 0.032(2) 0.0237(18) 0.0257(19) 0.0059(15) 0.0042(15) 0.0100(15) C24A 0.034(2) 0.020(2) 0.030(2) 0.0095(17) 0.0063(19) 0.0039(17) O25A 0.0278(16) 0.0321(17) 0.0236(16) 0.0050(13) -0.0036(13) 0.0040(13) C26A 0.032(2) 0.024(2) 0.025(2) -0.0004(17) -0.0010(18) 0.0058(18) O27A 0.0364(18) 0.0390(19) 0.0279(18) 0.0011(14) -0.0038(14) 0.0143(15) N28A 0.0284(19) 0.035(2) 0.027(2) 0.0007(16) 0.0042(16) 0.0127(16) C29A 0.031(2) 0.035(2) 0.024(2) 0.0019(18) 0.0018(18) 0.0106(19) O30A 0.0324(18) 0.054(2) 0.0299(18) -0.0004(15) 0.0016(14) 0.0214(16) C31A 0.049(3) 0.027(2) 0.028(2) 0.0106(18) 0.013(2) 0.020(2) C32A 0.039(3) 0.037(3) 0.032(2) 0.013(2) 0.011(2) 0.017(2) C33A 0.030(2) 0.048(3) 0.034(3) 0.027(2) 0.0103(19) 0.014(2) N41A 0.036(2) 0.035(2) 0.026(2) 0.0088(16) 0.0050(16) 0.0118(17) C42A 0.036(2) 0.032(2) 0.022(2) 0.0050(18) 0.0045(18) 0.0129(19) N43A 0.0298(19) 0.036(2) 0.0239(19) 0.0072(16) 0.0078(15) 0.0076(16) C44A 0.035(2) 0.041(3) 0.026(2) 0.012(2) 0.0021(19) 0.008(2) C45A 0.042(3) 0.047(3) 0.020(2) 0.009(2) 0.003(2) 0.010(2) C51A 0.033(2) 0.038(3) 0.028(2) 0.0002(19) 0.0055(19) 0.012(2) C52A 0.048(3) 0.039(3) 0.025(2) 0.0030(19) 0.001(2) 0.023(2) C53A 0.040(3) 0.045(3) 0.032(3) -0.003(2) 0.002(2) 0.026(2) N61A 0.0304(19) 0.038(2) 0.0213(19) -0.0041(16) 0.0030(15) 0.0139(17) C62A 0.030(2) 0.043(3) 0.023(2) -0.0019(19) 0.0013(18) 0.014(2) N63A 0.0287(19) 0.031(2) 0.0234(19) -0.0006(15) 0.0033(15) 0.0072(16) C64A 0.032(2) 0.042(3) 0.023(2) 0.0043(19) 0.0082(18) 0.013(2) C65A 0.030(2) 0.043(3) 0.027(2) -0.003(2) 0.0092(19) 0.012(2) C11B 0.038(2) 0.019(2) 0.029(2) 0.0057(17) 0.0040(19) 0.0092(18) C12B 0.029(2) 0.027(2) 0.027(2) 0.0025(17) -0.0005(18) 0.0119(18) C17B 0.030(2) 0.031(2) 0.032(2) 0.0022(19) 0.0022(19) 0.0142(19) C18B 0.031(2) 0.025(2) 0.024(2) 0.0019(17) 0.0040(17) 0.0120(18) C19B 0.026(2) 0.0164(19) 0.029(2) 0.0059(16) 0.0008(17) 0.0095(17) C31B 0.045(3) 0.024(2) 0.032(3) 0.0015(18) 0.013(2) 0.015(2) C32B 0.041(3) 0.030(2) 0.030(2) 0.0020(19) 0.008(2) 0.009(2) C33B 0.048(3) 0.031(3) 0.029(2) 0.000(2) 0.009(2) -0.001(2) C21B 0.036(2) 0.023(2) 0.025(2) 0.0036(17) 0.0010(19) 0.0101(18) O22B 0.0379(18) 0.043(2) 0.0272(18) 0.0010(14) 0.0005(15) 0.0099(15) N23B 0.034(2) 0.0260(19) 0.0217(18) 0.0023(14) 0.0043(15) 0.0137(16) C24B 0.032(2) 0.025(2) 0.027(2) -0.0025(17) 0.0029(18) 0.0130(18) O25B 0.0347(18) 0.0396(19) 0.0342(18) 0.0048(15) 0.0094(14) 0.0190(15) N41B 0.037(2) 0.032(2) 0.0233(19) -0.0009(15) 0.0048(16) 0.0083(17) C42B 0.040(3) 0.026(2) 0.029(2) 0.0021(18) 0.009(2) 0.009(2) N43B 0.032(2) 0.035(2) 0.0244(19) 0.0008(16) 0.0085(16) 0.0115(17) C44B 0.039(3) 0.039(3) 0.030(3) -0.004(2) -0.001(2) 0.011(2) C45B 0.056(3) 0.043(3) 0.033(3) -0.002(2) -0.001(2) 0.019(3) _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 N43A 2.268(4) . ? Mn1 N63A 2.269(4) 1_554 ? Mn1 N43B 2.290(4) . ? C11A C12A 1.375(7) . ? C11A C19A 1.418(6) . ? C11A C21A 1.478(6) . ? C12A C13A 1.378(7) . ? C12A H12A 0.9500 . ? C13A C14A 1.379(6) . ? C13A H13A 0.9500 . ? C14A C20A 1.408(6) . ? C14A C26A 1.462(6) . ? C15A C16A 1.380(7) . ? C15A C20A 1.405(6) . ? C15A C29A 1.473(6) . ? C16A C17A 1.414(7) . ? C16A H16A 0.9500 . ? C17A C18A 1.358(7) . ? C17A H17A 0.9500 . ? C18A C19A 1.415(6) . ? C18A C24A 1.500(6) . ? C19A C20A 1.408(6) . ? C21A O22A 1.222(6) . ? C21A N23A 1.397(6) . ? N23A C24A 1.388(6) . ? N23A C31A 1.487(6) . ? C24A O25A 1.211(6) . ? C26A O27A 1.216(6) . ? C26A N28A 1.403(6) . ? N28A C29A 1.384(6) . ? N28A C51A 1.484(6) . ? C29A O30A 1.227(6) . ? C31A C32A 1.525(6) . ? C31A H31A 0.9900 . ? C31A H31B 0.9900 . ? C32A C33A 1.510(6) . ? C32A H32A 0.9900 . ? C32A H32B 0.9900 . ? C33A N41A 1.483(6) . ? C33A H33A 0.9900 . ? C33A H33B 0.9900 . ? N41A C42A 1.345(6) . ? N41A C45A 1.346(7) . ? C42A N43A 1.308(6) . ? C42A H42A 0.9500 . ? N43A C44A 1.366(6) . ? C44A C45A 1.373(7) . ? C44A H44A 0.9500 . ? C45A H45A 0.9500 . ? C51A C52A 1.514(7) . ? C51A H51A 0.9900 . ? C51A H51B 0.9900 . ? C52A C53A 1.522(7) . ? C52A H52A 0.9900 . ? C52A H52B 0.9900 . ? C53A N61A 1.469(6) . ? C53A H53A 0.9900 . ? C53A H53B 0.9900 . ? N61A C62A 1.345(6) . ? N61A C65A 1.354(7) . ? C62A N63A 1.317(7) . ? C62A H62A 0.9500 . ? N63A C64A 1.389(6) . ? N63A Mn1 2.269(4) 1_556 ? C64A C65A 1.355(7) . ? C64A H64A 0.9500 . ? C65A H65A 0.9500 . ? C11B C12B 1.370(7) . ? C11B C19B 1.413(6) . ? C11B C21B 1.485(6) . ? C12B C17B 1.416(6) 2_755 ? C12B H12B 0.9500 . ? C17B C18B 1.357(7) . ? C17B C12B 1.416(6) 2_755 ? C17B H17B 0.9500 . ? C18B C19B 1.417(6) . ? C18B C24B 1.488(6) . ? C19B C19B 1.408(9) 2_755 ? C31B N23B 1.460(6) . ? C31B C32B 1.524(7) . ? C31B H31C 0.9900 . ? C31B H31D 0.9900 . ? C32B C33B 1.515(7) . ? C32B H32C 0.9900 . ? C32B H32D 0.9900 . ? C33B N41B 1.462(6) . ? C33B H33C 0.9900 . ? C33B H33D 0.9900 . ? C21B O22B 1.201(6) . ? C21B N23B 1.398(6) . ? N23B C24B 1.405(6) . ? C24B O25B 1.210(6) . ? N41B C42B 1.344(6) . ? N41B C45B 1.351(7) . ? C42B N43B 1.332(6) . ? C42B H42B 0.9500 . ? N43B C44B 1.376(7) . ? C44B C45B 1.354(8) . ? C44B H44B 0.9500 . ? C45B H45B 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 N43A Mn1 N63A 93.44(14) 2_766 2_767 ? N43A Mn1 N63A 86.56(14) . 2_767 ? N43A Mn1 N63A 86.56(14) 2_766 1_554 ? N43A Mn1 N63A 93.44(14) . 1_554 ? N43A Mn1 N43B 88.68(14) 2_766 2_766 ? N43A Mn1 N43B 91.32(14) . 2_766 ? N63A Mn1 N43B 86.70(14) 2_767 2_766 ? N63A Mn1 N43B 93.30(14) 1_554 2_766 ? N43A Mn1 N43B 91.32(14) 2_766 . ? N43A Mn1 N43B 88.68(14) . . ? N63A Mn1 N43B 93.30(14) 2_767 . ? N63A Mn1 N43B 86.70(14) 1_554 . ? C12A C11A C19A 120.2(4) . . ? C12A C11A C21A 120.6(4) . . ? C19A C11A C21A 119.2(4) . . ? C11A C12A C13A 120.3(4) . . ? C11A C12A H12A 119.9 . . ? C13A C12A H12A 119.9 . . ? C12A C13A C14A 121.3(4) . . ? C12A C13A H13A 119.4 . . ? C14A C13A H13A 119.4 . . ? C13A C14A C20A 119.8(4) . . ? C13A C14A C26A 120.7(4) . . ? C20A C14A C26A 119.5(4) . . ? C16A C15A C20A 120.3(4) . . ? C16A C15A C29A 120.1(4) . . ? C20A C15A C29A 119.5(4) . . ? C15A C16A C17A 120.1(4) . . ? C15A C16A H16A 120.0 . . ? C17A C16A H16A 120.0 . . ? C18A C17A C16A 120.1(4) . . ? C18A C17A H17A 120.0 . . ? C16A C17A H17A 120.0 . . ? C17A C18A C19A 120.9(4) . . ? C17A C18A C24A 120.4(4) . . ? C19A C18A C24A 118.8(4) . . ? C20A C19A C18A 119.2(4) . . ? C20A C19A C11A 119.0(4) . . ? C18A C19A C11A 121.8(4) . . ? C15A C20A C19A 119.3(4) . . ? C15A C20A C14A 121.4(4) . . ? C19A C20A C14A 119.3(4) . . ? O22A C21A N23A 119.8(4) . . ? O22A C21A C11A 122.5(4) . . ? N23A C21A C11A 117.6(4) . . ? C24A N23A C21A 125.0(4) . . ? C24A N23A C31A 118.0(4) . . ? C21A N23A C31A 116.9(4) . . ? O25A C24A N23A 121.1(4) . . ? O25A C24A C18A 121.7(4) . . ? N23A C24A C18A 117.2(4) . . ? O27A C26A N28A 119.5(4) . . ? O27A C26A C14A 123.3(4) . . ? N28A C26A C14A 117.2(4) . . ? C29A N28A C26A 124.7(4) . . ? C29A N28A C51A 117.8(4) . . ? C26A N28A C51A 117.1(4) . . ? O30A C29A N28A 120.1(4) . . ? O30A C29A C15A 122.6(4) . . ? N28A C29A C15A 117.2(4) . . ? N23A C31A C32A 113.0(4) . . ? N23A C31A H31A 109.0 . . ? C32A C31A H31A 109.0 . . ? N23A C31A H31B 109.0 . . ? C32A C31A H31B 109.0 . . ? H31A C31A H31B 107.8 . . ? C33A C32A C31A 112.3(4) . . ? C33A C32A H32A 109.1 . . ? C31A C32A H32A 109.1 . . ? C33A C32A H32B 109.1 . . ? C31A C32A H32B 109.1 . . ? H32A C32A H32B 107.9 . . ? N41A C33A C32A 110.9(4) . . ? N41A C33A H33A 109.5 . . ? C32A C33A H33A 109.5 . . ? N41A C33A H33B 109.5 . . ? C32A C33A H33B 109.5 . . ? H33A C33A H33B 108.1 . . ? C42A N41A C45A 108.4(4) . . ? C42A N41A C33A 126.4(4) . . ? C45A N41A C33A 125.2(4) . . ? N43A C42A N41A 111.1(4) . . ? N43A C42A H42A 124.5 . . ? N41A C42A H42A 124.5 . . ? C42A N43A C44A 105.6(4) . . ? C42A N43A Mn1 129.3(3) . . ? C44A N43A Mn1 125.0(3) . . ? N43A C44A C45A 109.8(5) . . ? N43A C44A H44A 125.1 . . ? C45A C44A H44A 125.1 . . ? N41A C45A C44A 105.2(4) . . ? N41A C45A H45A 127.4 . . ? C44A C45A H45A 127.4 . . ? N28A C51A C52A 109.6(4) . . ? N28A C51A H51A 109.7 . . ? C52A C51A H51A 109.7 . . ? N28A C51A H51B 109.7 . . ? C52A C51A H51B 109.7 . . ? H51A C51A H51B 108.2 . . ? C51A C52A C53A 112.7(4) . . ? C51A C52A H52A 109.0 . . ? C53A C52A H52A 109.0 . . ? C51A C52A H52B 109.0 . . ? C53A C52A H52B 109.0 . . ? H52A C52A H52B 107.8 . . ? N61A C53A C52A 110.5(4) . . ? N61A C53A H53A 109.5 . . ? C52A C53A H53A 109.5 . . ? N61A C53A H53B 109.5 . . ? C52A C53A H53B 109.5 . . ? H53A C53A H53B 108.1 . . ? C62A N61A C65A 107.2(4) . . ? C62A N61A C53A 125.3(5) . . ? C65A N61A C53A 127.5(4) . . ? N63A C62A N61A 111.6(5) . . ? N63A C62A H62A 124.2 . . ? N61A C62A H62A 124.2 . . ? C62A N63A C64A 105.2(4) . . ? C62A N63A Mn1 126.6(3) . 1_556 ? C64A N63A Mn1 127.6(3) . 1_556 ? C65A C64A N63A 108.9(4) . . ? C65A C64A H64A 125.6 . . ? N63A C64A H64A 125.6 . . ? N61A C65A C64A 107.1(4) . . ? N61A C65A H65A 126.5 . . ? C64A C65A H65A 126.5 . . ? C12B C11B C19B 119.8(4) . . ? C12B C11B C21B 119.9(4) . . ? C19B C11B C21B 120.4(4) . . ? C11B C12B C17B 120.4(4) . 2_755 ? C11B C12B H12B 119.8 . . ? C17B C12B H12B 119.8 2_755 . ? C18B C17B C12B 120.5(4) . 2_755 ? C18B C17B H17B 119.7 . . ? C12B C17B H17B 119.7 2_755 . ? C17B C18B C19B 120.5(4) . . ? C17B C18B C24B 120.1(4) . . ? C19B C18B C24B 119.4(4) . . ? C19B C19B C11B 119.9(5) 2_755 . ? C19B C19B C18B 118.9(5) 2_755 . ? C11B C19B C18B 121.1(4) . . ? N23B C31B C32B 112.3(4) . . ? N23B C31B H31C 109.1 . . ? C32B C31B H31C 109.1 . . ? N23B C31B H31D 109.1 . . ? C32B C31B H31D 109.1 . . ? H31C C31B H31D 107.9 . . ? C33B C32B C31B 111.9(4) . . ? C33B C32B H32C 109.2 . . ? C31B C32B H32C 109.2 . . ? C33B C32B H32D 109.2 . . ? C31B C32B H32D 109.2 . . ? H32C C32B H32D 107.9 . . ? N41B C33B C32B 112.1(4) . . ? N41B C33B H33C 109.2 . . ? C32B C33B H33C 109.2 . . ? N41B C33B H33D 109.2 . . ? C32B C33B H33D 109.2 . . ? H33C C33B H33D 107.9 . . ? O22B C21B N23B 120.8(4) . . ? O22B C21B C11B 122.6(4) . . ? N23B C21B C11B 116.6(4) . . ? C21B N23B C24B 125.1(4) . . ? C21B N23B C31B 117.3(4) . . ? C24B N23B C31B 117.6(4) . . ? O25B C24B N23B 120.4(4) . . ? O25B C24B C18B 122.4(4) . . ? N23B C24B C18B 117.2(4) . . ? C42B N41B C45B 107.3(4) . . ? C42B N41B C33B 125.9(5) . . ? C45B N41B C33B 126.8(5) . . ? N43B C42B N41B 111.8(4) . . ? N43B C42B H42B 124.1 . . ? N41B C42B H42B 124.1 . . ? C42B N43B C44B 104.0(4) . . ? C42B N43B Mn1 129.2(3) . . ? C44B N43B Mn1 126.7(3) . . ? C45B C44B N43B 110.4(5) . . ? C45B C44B H44B 124.8 . . ? N43B C44B H44B 124.8 . . ? N41B C45B C44B 106.4(5) . . ? N41B C45B H45B 126.8 . . ? C44B C45B H45B 126.8 . . ? 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 C19A C11A C12A C13A 3.2(7) . . . . ? C21A C11A C12A C13A -175.6(4) . . . . ? C11A C12A C13A C14A -0.2(7) . . . . ? C12A C13A C14A C20A -3.1(7) . . . . ? C12A C13A C14A C26A 175.2(4) . . . . ? C20A C15A C16A C17A 4.3(7) . . . . ? C29A C15A C16A C17A -178.6(4) . . . . ? C15A C16A C17A C18A -3.3(7) . . . . ? C16A C17A C18A C19A 0.2(7) . . . . ? C16A C17A C18A C24A -179.9(4) . . . . ? C17A C18A C19A C20A 1.8(7) . . . . ? C24A C18A C19A C20A -178.0(4) . . . . ? C17A C18A C19A C11A -178.2(4) . . . . ? C24A C18A C19A C11A 2.0(6) . . . . ? C12A C11A C19A C20A -2.9(6) . . . . ? C21A C11A C19A C20A 175.9(4) . . . . ? C12A C11A C19A C18A 177.2(4) . . . . ? C21A C11A C19A C18A -4.1(6) . . . . ? C16A C15A C20A C19A -2.2(7) . . . . ? C29A C15A C20A C19A -179.3(4) . . . . ? C16A C15A C20A C14A 177.3(4) . . . . ? C29A C15A C20A C14A 0.1(7) . . . . ? C18A C19A C20A C15A -0.9(6) . . . . ? C11A C19A C20A C15A 179.2(4) . . . . ? C18A C19A C20A C14A 179.6(4) . . . . ? C11A C19A C20A C14A -0.3(6) . . . . ? C13A C14A C20A C15A -176.2(4) . . . . ? C26A C14A C20A C15A 5.5(6) . . . . ? C13A C14A C20A C19A 3.3(6) . . . . ? C26A C14A C20A C19A -175.0(4) . . . . ? C12A C11A C21A O22A 2.3(7) . . . . ? C19A C11A C21A O22A -176.4(4) . . . . ? C12A C11A C21A N23A 178.9(4) . . . . ? C19A C11A C21A N23A 0.1(6) . . . . ? O22A C21A N23A C24A -176.9(4) . . . . ? C11A C21A N23A C24A 6.4(6) . . . . ? O22A C21A N23A C31A 0.2(6) . . . . ? C11A C21A N23A C31A -176.5(4) . . . . ? C21A N23A C24A O25A 171.0(4) . . . . ? C31A N23A C24A O25A -6.0(6) . . . . ? C21A N23A C24A C18A -8.5(6) . . . . ? C31A N23A C24A C18A 174.5(4) . . . . ? C17A C18A C24A O25A 4.7(7) . . . . ? C19A C18A C24A O25A -175.5(4) . . . . ? C17A C18A C24A N23A -175.8(4) . . . . ? C19A C18A C24A N23A 4.1(6) . . . . ? C13A C14A C26A O27A -5.3(7) . . . . ? C20A C14A C26A O27A 173.0(4) . . . . ? C13A C14A C26A N28A 176.3(4) . . . . ? C20A C14A C26A N28A -5.5(6) . . . . ? O27A C26A N28A C29A -178.8(4) . . . . ? C14A C26A N28A C29A -0.2(7) . . . . ? O27A C26A N28A C51A 7.5(6) . . . . ? C14A C26A N28A C51A -174.0(4) . . . . ? C26A N28A C29A O30A -177.5(4) . . . . ? C51A N28A C29A O30A -3.8(7) . . . . ? C26A N28A C29A C15A 5.7(7) . . . . ? C51A N28A C29A C15A 179.4(4) . . . . ? C16A C15A C29A O30A 0.5(7) . . . . ? C20A C15A C29A O30A 177.7(5) . . . . ? C16A C15A C29A N28A 177.2(4) . . . . ? C20A C15A C29A N28A -5.7(6) . . . . ? C24A N23A C31A C32A 95.9(5) . . . . ? C21A N23A C31A C32A -81.3(5) . . . . ? N23A C31A C32A C33A -70.2(6) . . . . ? C31A C32A C33A N41A 176.9(4) . . . . ? C32A C33A N41A C42A 101.7(6) . . . . ? C32A C33A N41A C45A -79.9(6) . . . . ? C45A N41A C42A N43A -1.8(6) . . . . ? C33A N41A C42A N43A 176.9(4) . . . . ? N41A C42A N43A C44A 1.0(5) . . . . ? N41A C42A N43A Mn1 -175.1(3) . . . . ? N63A Mn1 N43A C42A -121.5(4) 2_767 . . . ? N63A Mn1 N43A C42A 58.5(4) 1_554 . . . ? N43B Mn1 N43A C42A 151.8(4) 2_766 . . . ? N43B Mn1 N43A C42A -28.2(4) . . . . ? N63A Mn1 N43A C44A 63.0(4) 2_767 . . . ? N63A Mn1 N43A C44A -117.0(4) 1_554 . . . ? N43B Mn1 N43A C44A -23.6(4) 2_766 . . . ? N43B Mn1 N43A C44A 156.4(4) . . . . ? C42A N43A C44A C45A 0.0(6) . . . . ? Mn1 N43A C44A C45A 176.4(3) . . . . ? C42A N41A C45A C44A 1.7(6) . . . . ? C33A N41A C45A C44A -177.0(4) . . . . ? N43A C44A C45A N41A -1.1(6) . . . . ? C29A N28A C51A C52A -92.1(5) . . . . ? C26A N28A C51A C52A 82.1(5) . . . . ? N28A C51A C52A C53A -168.7(4) . . . . ? C51A C52A C53A N61A 62.1(6) . . . . ? C52A C53A N61A C62A 78.1(6) . . . . ? C52A C53A N61A C65A -102.3(5) . . . . ? C65A N61A C62A N63A 0.6(5) . . . . ? C53A N61A C62A N63A -179.8(4) . . . . ? N61A C62A N63A C64A -0.2(5) . . . . ? N61A C62A N63A Mn1 172.0(3) . . . 1_556 ? C62A N63A C64A C65A -0.2(5) . . . . ? Mn1 N63A C64A C65A -172.3(3) 1_556 . . . ? C62A N61A C65A C64A -0.7(5) . . . . ? C53A N61A C65A C64A 179.7(4) . . . . ? N63A C64A C65A N61A 0.6(5) . . . . ? C19B C11B C12B C17B 1.1(7) . . . 2_755 ? C21B C11B C12B C17B -179.0(4) . . . 2_755 ? C12B C17B C18B C19B 0.1(7) 2_755 . . . ? C12B C17B C18B C24B 179.7(4) 2_755 . . . ? C12B C11B C19B C19B -0.6(7) . . . 2_755 ? C21B C11B C19B C19B 179.5(4) . . . 2_755 ? C12B C11B C19B C18B 179.2(4) . . . . ? C21B C11B C19B C18B -0.8(6) . . . . ? C17B C18B C19B C19B -0.6(7) . . . 2_755 ? C24B C18B C19B C19B 179.8(4) . . . 2_755 ? C17B C18B C19B C11B 179.7(4) . . . . ? C24B C18B C19B C11B 0.1(6) . . . . ? N23B C31B C32B C33B -171.9(4) . . . . ? C31B C32B C33B N41B -63.3(6) . . . . ? C12B C11B C21B O22B -0.1(7) . . . . ? C19B C11B C21B O22B 179.9(4) . . . . ? C12B C11B C21B N23B 178.3(4) . . . . ? C19B C11B C21B N23B -1.8(6) . . . . ? O22B C21B N23B C24B -176.0(4) . . . . ? C11B C21B N23B C24B 5.5(6) . . . . ? O22B C21B N23B C31B 0.1(6) . . . . ? C11B C21B N23B C31B -178.3(4) . . . . ? C32B C31B N23B C21B -83.9(5) . . . . ? C32B C31B N23B C24B 92.6(5) . . . . ? C21B N23B C24B O25B 173.3(4) . . . . ? C31B N23B C24B O25B -2.9(6) . . . . ? C21B N23B C24B C18B -6.3(6) . . . . ? C31B N23B C24B C18B 177.6(4) . . . . ? C17B C18B C24B O25B 4.1(7) . . . . ? C19B C18B C24B O25B -176.3(4) . . . . ? C17B C18B C24B N23B -176.4(4) . . . . ? C19B C18B C24B N23B 3.3(6) . . . . ? C32B C33B N41B C42B 114.4(5) . . . . ? C32B C33B N41B C45B -65.8(7) . . . . ? C45B N41B C42B N43B -0.3(6) . . . . ? C33B N41B C42B N43B 179.5(4) . . . . ? N41B C42B N43B C44B 0.5(5) . . . . ? N41B C42B N43B Mn1 -176.5(3) . . . . ? N43A Mn1 N43B C42B -73.6(4) 2_766 . . . ? N43A Mn1 N43B C42B 106.4(4) . . . . ? N63A Mn1 N43B C42B -167.1(4) 2_767 . . . ? N63A Mn1 N43B C42B 12.9(4) 1_554 . . . ? N43A Mn1 N43B C44B 110.0(4) 2_766 . . . ? N43A Mn1 N43B C44B -70.0(4) . . . . ? N63A Mn1 N43B C44B 16.4(4) 2_767 . . . ? N63A Mn1 N43B C44B -163.6(4) 1_554 . . . ? C42B N43B C44B C45B -0.6(6) . . . . ? Mn1 N43B C44B C45B 176.6(4) . . . . ? C42B N41B C45B C44B 0.0(6) . . . . ? C33B N41B C45B C44B -179.9(5) . . . . ? N43B C44B C45B N41B 0.4(6) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 942765' ####################################################################### # # 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_mnvrld _nottingham_internal_coll_name MNVRLD _nottingham_internal_coll_number 9929 _nottingham_internal_coll_client VJR/NRC _nottingham_internal_coll_type hemisphere _nottingham_internal_coll_frame_time '40 s' _nottingham_internal_coll_frame_width '0.3 degrees' _nottingham_internal_coll_frame_method \w _nottingham_internal_coll_user VJR _nottingham_internal_coll_date 30/11/10 _nottingham_internal_process_user VJR/WL _nottingham_internal_process_date 01/12/2010 _nottingham_internal_solution_user VJR _nottingham_internal_solution_date 02/12/2010 _nottingham_internal_refinement_user VJR/SPA _nottingham_internal_refinement_date 28/01/2012 _nottingham_internal_validation_user AJB _nottingham_internal_validation_date 31/1/2012 _nottingham_internal_archive_date ? _refine_special_details ; The DMF solvent molecule is disordered over a symmetry axis and each component is of 0.5 occupancy. All inappropriate bonds between symmetry generated atoms were removed from the connectivity list by means of a PART -1 instructions. The entire molecule was refined isotropically and bond distances were refined and restrained to be O1A-C2A 1.25(1) \%A, C2A-N3A 1.35(1) \%A, C4A...C5A 2.55(1) \%A. Chemically equivalent 1,3- distances C2A...C4A and C2A..C5A were restrained to be approximately equal and chemically equivalent 1,2-distances C2A-N3A and C4A-C5A were also restrained to be approximately equal. All NON-hatoms of the DMF molecule are restrained to be coplanar by means of a FLAT instruction. Rigid bond and similarity restraints were applied to the atomic displacement parameters of atoms C52 and C53. ; _audit_creation_date 2012-01-28 _audit_creation_method ; Olex2 1.1 (compiled Nov 1 2011 20:42:30, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C52 H44 Mn N14 O14, C3 H7 N O' _chemical_formula_sum 'C55 H51 Mn N15 O15' _chemical_formula_weight 1217.05 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 35.385(11) _cell_length_b 8.383(3) _cell_length_c 20.831(6) _cell_angle_alpha 90.00 _cell_angle_beta 122.313(5) _cell_angle_gamma 90.00 _cell_volume 5222(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3537 _cell_measurement_temperature 90(2) _cell_measurement_theta_max 27.558 _cell_measurement_theta_min 2.313 _exptl_absorpt_coefficient_mu 0.342 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_correction_T_min 0.558 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2007/2 (Bruker,2007) was used for absorption correction. R(int) was 0.0909 before and 0.0621 after correction. The Ratio of minimum to maximum transmission is 0.7488. The \l/2 correction factor is 0.0015. ; _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_min 0.04 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_max 0.48 _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_F_000 2524 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.071 _diffrn_reflns_av_unetI/netI 0.098 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 12082 _diffrn_reflns_theta_full 25.10 _diffrn_reflns_theta_max 25.10 _diffrn_reflns_theta_min 1.36 _diffrn_measured_fraction_theta_full 0.960 _diffrn_measured_fraction_theta_max 0.960 _diffrn_detector_area_resol_mean 8.192 _diffrn_ambient_temperature 90(2) _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method \w _diffrn_radiation_wavelength 0.71073 _reflns_number_gt 2905 _reflns_number_total 4445 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36A (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _refine_diff_density_max 0.58 _refine_diff_density_min -0.60 _refine_diff_density_rms 0.11 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 390 _refine_ls_number_reflns 4445 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.127 _refine_ls_R_factor_gt 0.0839 _refine_ls_restrained_S_all 1.08 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.018P)^2^+94.96P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.182 _refine_ls_wR_factor_ref 0.199 _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 C11 C 0.5221(2) 0.3356(8) 0.4198(4) 0.0170(15) Uani 1 1 d . . . C12 C 0.5616(2) 0.2546(9) 0.4656(4) 0.0224(15) Uani 1 1 d . . . H12 H 0.5640 0.1458 0.4554 0.027 Uiso 1 1 calc R . . C13 C 0.5980(2) 0.3314(8) 0.5266(4) 0.0187(15) Uani 1 1 d . . . H13 H 0.6250 0.2745 0.5582 0.022 Uiso 1 1 calc R . . C14 C 0.5950(2) 0.4904(8) 0.5416(3) 0.0172(15) Uani 1 1 d . . . C15 C 0.5514(2) 0.7371(9) 0.5085(3) 0.0185(14) Uani 1 1 d . . . C16 C 0.5133(2) 0.8197(8) 0.4605(4) 0.0194(15) Uani 1 1 d . . . H16 H 0.5118 0.9305 0.4687 0.023 Uiso 1 1 calc R . . C17 C 0.4759(2) 0.7432(9) 0.3990(3) 0.0209(15) Uani 1 1 d . . . H17 H 0.4492 0.8016 0.3667 0.025 Uiso 1 1 calc R . . C18 C 0.4782(2) 0.5827(9) 0.3862(3) 0.0178(15) Uani 1 1 d . . . C19 C 0.5182(2) 0.4983(8) 0.4334(3) 0.0172(15) Uani 1 1 d . . . C20 C 0.5553(2) 0.5734(8) 0.4952(3) 0.0155(14) Uani 1 1 d . . . C21 C 0.4829(2) 0.2541(9) 0.3559(4) 0.0204(14) Uani 1 1 d . . . C24 C 0.4390(2) 0.5025(9) 0.3222(4) 0.0213(16) Uani 1 1 d . . . C26 C 0.6337(2) 0.5695(9) 0.6062(4) 0.0197(15) Uani 1 1 d . . . C29 C 0.5893(2) 0.8183(8) 0.5744(4) 0.0192(15) Uani 1 1 d . . . C31 C 0.4042(2) 0.2584(10) 0.2511(3) 0.0238(15) Uani 1 1 d . . . H31A H 0.3768 0.3113 0.2427 0.029 Uiso 1 1 calc R . . H31B H 0.4037 0.1465 0.2659 0.029 Uiso 1 1 calc R . . C32 C 0.4030(2) 0.2594(9) 0.1769(3) 0.0231(15) Uani 1 1 d . . . H32A H 0.4065 0.3702 0.1644 0.028 Uiso 1 1 calc R . . H32B H 0.4282 0.1956 0.1830 0.028 Uiso 1 1 calc R . . C33 C 0.3593(2) 0.1912(8) 0.1123(4) 0.0232(16) Uani 1 1 d . . . H33A H 0.3614 0.1759 0.0673 0.028 Uiso 1 1 calc R . . H33B H 0.3540 0.0856 0.1275 0.028 Uiso 1 1 calc R . . C42 C 0.3134(2) 0.4396(8) 0.0571(3) 0.0192(15) Uani 1 1 d . . . H42 H 0.3322 0.4874 0.0429 0.023 Uiso 1 1 calc R . . C44 C 0.2588(2) 0.3977(9) 0.0717(4) 0.0211(16) Uani 1 1 d . . . H44 H 0.2316 0.4114 0.0700 0.025 Uiso 1 1 calc R . . C45 C 0.2864(2) 0.2693(9) 0.1016(4) 0.0228(16) Uani 1 1 d . . . H45 H 0.2822 0.1784 0.1243 0.027 Uiso 1 1 calc R . . C51 C 0.6657(2) 0.8094(8) 0.6851(4) 0.0190(15) Uani 1 1 d . . . H51A H 0.6864 0.7282 0.7214 0.023 Uiso 1 1 calc R . . H51B H 0.6547 0.8747 0.7113 0.023 Uiso 1 1 calc R . . C52 C 0.6912(2) 0.9164(9) 0.6615(4) 0.0205(15) Uani 1 1 d U . . H52A H 0.7012 0.8518 0.6334 0.025 Uiso 1 1 calc R . . H52B H 0.6708 1.0001 0.6267 0.025 Uiso 1 1 calc R . . C53 C 0.7315(2) 0.9950(9) 0.7288(4) 0.0248(17) Uani 1 1 d U . . H53A H 0.7537 0.9118 0.7602 0.030 Uiso 1 1 calc R . . H53B H 0.7456 1.0675 0.7100 0.030 Uiso 1 1 calc R . . C62 C 0.7457(2) 1.0943(8) 0.8535(3) 0.0173(15) Uani 1 1 d . . . H62 H 0.7733 1.0400 0.8840 0.021 Uiso 1 1 calc R . . C64 C 0.6883(2) 1.2407(9) 0.8176(3) 0.0236(15) Uani 1 1 d . . . H64 H 0.6677 1.3108 0.8192 0.028 Uiso 1 1 calc R . . C65 C 0.6833(2) 1.1804(9) 0.7532(4) 0.0250(16) Uani 1 1 d . . . H65 H 0.6593 1.1991 0.7025 0.030 Uiso 1 1 calc R . . N1 N 0.34668(19) 0.8175(7) 0.0173(3) 0.0198(13) Uani 1 1 d . . . N23 N 0.44338(18) 0.3386(7) 0.3138(3) 0.0178(12) Uani 1 1 d . . . N28 N 0.62781(16) 0.7290(7) 0.6203(3) 0.0151(12) Uani 1 1 d . . . N41 N 0.32154(18) 0.2967(6) 0.0925(3) 0.0168(12) Uani 1 1 d . . . N43 N 0.27638(17) 0.5037(6) 0.0447(3) 0.0147(12) Uani 1 1 d . . . N61 N 0.72009(18) 1.0868(7) 0.7768(3) 0.0174(12) Uani 1 1 d . . . N63 N 0.72710(17) 1.1870(7) 0.8801(3) 0.0172(12) Uani 1 1 d . . . O1 O 0.31614(15) 0.8552(6) 0.0275(3) 0.0259(12) Uani 1 1 d . . . O2 O 0.37416(17) 0.9199(7) 0.0241(3) 0.0336(13) Uani 1 1 d . . . O3 O 0.3487(2) 0.6801(6) -0.0026(3) 0.0435(16) Uani 1 1 d . . . O22 O 0.48417(16) 0.1133(6) 0.3414(3) 0.0261(12) Uani 1 1 d . . . O25 O 0.40392(16) 0.5706(6) 0.2800(3) 0.0278(12) Uani 1 1 d . . . O27 O 0.66924(15) 0.5038(6) 0.6471(3) 0.0218(11) Uani 1 1 d . . . O30 O 0.58748(16) 0.9563(6) 0.5910(3) 0.0235(11) Uani 1 1 d . . . Mn1 Mn 0.2500 0.7500 0.0000 0.0141(3) Uani 1 2 d S . . C2A C 0.4800(4) 0.5854(16) 0.2206(7) 0.019(3) Uiso 0.50 1 d PD A -1 H2A H 0.4505 0.5628 0.1794 0.023 Uiso 0.50 1 calc PR A -1 C4A C 0.5358(5) 0.781(2) 0.2993(9) 0.034(4) Uiso 0.50 1 d PD A -1 H4AA H 0.5511 0.6882 0.3312 0.052 Uiso 0.50 1 calc PR A -1 H4AB H 0.5340 0.8654 0.3304 0.052 Uiso 0.50 1 calc PR A -1 H4AC H 0.5525 0.8208 0.2773 0.052 Uiso 0.50 1 calc PR A -1 C5A C 0.4588(5) 0.864(2) 0.2001(9) 0.033(4) Uiso 0.50 1 d PD A -1 H5AA H 0.4689 0.9344 0.1747 0.050 Uiso 0.50 1 calc PR A -1 H5AB H 0.4555 0.9257 0.2368 0.050 Uiso 0.50 1 calc PR A -1 H5AC H 0.4299 0.8170 0.1622 0.050 Uiso 0.50 1 calc PR A -1 N3A N 0.4915(4) 0.7372(12) 0.2395(7) 0.023(3) Uiso 0.50 1 d PD A -1 O1A O 0.5059(5) 0.4704(10) 0.2544(10) 0.030(3) Uiso 0.50 1 d PD A -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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C11 0.020(4) 0.016(4) 0.019(3) 0.002(3) 0.013(3) -0.001(3) C12 0.026(4) 0.018(4) 0.024(3) 0.001(3) 0.014(3) -0.002(4) C13 0.020(4) 0.015(4) 0.023(4) 0.001(3) 0.012(3) 0.000(3) C14 0.024(4) 0.016(4) 0.016(3) 0.002(3) 0.013(3) 0.000(3) C15 0.024(4) 0.020(4) 0.019(3) 0.002(3) 0.016(3) 0.000(3) C16 0.028(4) 0.014(4) 0.023(4) -0.005(3) 0.018(3) -0.002(3) C17 0.023(3) 0.026(4) 0.017(3) 0.004(3) 0.013(3) 0.008(4) C18 0.018(4) 0.028(4) 0.014(3) -0.003(3) 0.013(3) -0.002(3) C19 0.019(4) 0.021(4) 0.014(3) 0.004(3) 0.010(3) 0.001(3) C20 0.020(4) 0.015(4) 0.016(3) 0.003(3) 0.013(3) 0.001(3) C21 0.026(4) 0.020(4) 0.022(3) 0.002(3) 0.018(3) -0.002(4) C24 0.021(4) 0.028(4) 0.017(3) 0.001(3) 0.011(3) 0.001(3) C26 0.021(4) 0.024(4) 0.019(3) 0.007(3) 0.013(3) -0.001(3) C29 0.026(4) 0.020(4) 0.022(4) 0.005(3) 0.020(3) 0.002(3) C31 0.026(4) 0.024(4) 0.019(3) -0.001(3) 0.011(3) -0.007(4) C32 0.029(4) 0.020(4) 0.020(3) 0.000(3) 0.014(3) 0.004(4) C33 0.033(4) 0.016(4) 0.021(4) -0.002(3) 0.015(3) 0.004(3) C42 0.020(4) 0.022(4) 0.017(3) -0.003(3) 0.012(3) 0.001(3) C44 0.021(4) 0.027(4) 0.016(3) -0.010(3) 0.011(3) -0.005(3) C45 0.034(4) 0.015(4) 0.021(3) -0.006(3) 0.016(3) -0.009(3) C51 0.020(4) 0.019(4) 0.022(3) -0.005(3) 0.014(3) -0.008(3) C52 0.024(4) 0.021(4) 0.021(3) -0.005(3) 0.015(3) 0.000(3) C53 0.022(4) 0.038(5) 0.025(4) -0.017(3) 0.020(3) -0.010(3) C62 0.019(4) 0.020(4) 0.017(3) -0.002(3) 0.012(3) -0.004(3) C64 0.027(4) 0.023(4) 0.019(3) 0.000(3) 0.011(3) 0.005(4) C65 0.034(4) 0.023(4) 0.013(3) -0.003(3) 0.009(3) -0.001(4) N1 0.027(3) 0.024(3) 0.014(3) -0.004(3) 0.015(3) -0.003(3) N23 0.020(3) 0.020(3) 0.017(3) 0.006(3) 0.013(2) 0.002(3) N28 0.016(3) 0.014(3) 0.014(3) 0.001(2) 0.007(2) 0.000(2) N41 0.022(3) 0.010(3) 0.012(3) 0.000(2) 0.005(2) 0.000(2) N43 0.022(3) 0.016(3) 0.011(3) -0.001(2) 0.012(2) -0.003(3) N61 0.023(3) 0.020(3) 0.015(3) -0.005(2) 0.014(3) -0.002(3) N63 0.023(3) 0.018(3) 0.013(3) -0.006(2) 0.011(3) -0.004(3) O1 0.022(3) 0.029(3) 0.036(3) -0.006(2) 0.021(2) -0.001(2) O2 0.037(3) 0.039(3) 0.041(3) -0.013(3) 0.031(3) -0.015(3) O3 0.089(5) 0.017(3) 0.067(4) 0.001(3) 0.071(4) 0.004(3) O22 0.029(3) 0.014(3) 0.029(3) 0.000(2) 0.011(2) 0.001(2) O25 0.020(3) 0.032(3) 0.024(3) 0.000(2) 0.006(2) 0.006(2) O27 0.019(3) 0.021(3) 0.024(3) 0.000(2) 0.010(2) -0.002(2) O30 0.032(3) 0.016(3) 0.027(3) -0.008(2) 0.019(2) 0.000(2) Mn1 0.0204(7) 0.0128(7) 0.0134(7) -0.0017(6) 0.0119(6) 0.0005(7) _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 C11 C12 1.378(9) . ? C11 C19 1.414(9) . ? C11 C21 1.481(9) . ? C12 C13 1.392(9) . ? C12 H12 0.9500 . ? C13 C14 1.386(9) . ? C13 H13 0.9500 . ? C14 C20 1.392(9) . ? C14 C26 1.469(9) . ? C15 C16 1.363(9) . ? C15 C20 1.421(10) . ? C15 C29 1.475(9) . ? C16 C17 1.412(9) . ? C16 H16 0.9500 . ? C17 C18 1.382(10) . ? C17 H17 0.9500 . ? C18 C19 1.410(9) . ? C18 C24 1.476(9) . ? C19 C20 1.404(9) . ? C21 O22 1.225(9) . ? C21 N23 1.383(9) . ? C24 O25 1.213(8) . ? C24 N23 1.405(9) . ? C26 O27 1.211(8) . ? C26 N28 1.408(9) . ? C29 O30 1.220(8) . ? C29 N28 1.393(8) . ? C31 N23 1.465(8) . ? C31 C32 1.525(8) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.518(9) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 N41 1.465(8) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C42 N43 1.307(8) . ? C42 N41 1.355(8) . ? C42 H42 0.9500 . ? C44 C45 1.360(10) . ? C44 N43 1.366(8) . ? C44 H44 0.9500 . ? C45 N41 1.372(8) . ? C45 H45 0.9500 . ? C51 N28 1.462(8) . ? C51 C52 1.528(9) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 C53 1.516(9) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 N61 1.479(8) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C62 N63 1.317(8) . ? C62 N61 1.353(8) . ? C62 H62 0.9500 . ? C64 C65 1.355(9) . ? C64 N63 1.368(8) . ? C64 H64 0.9500 . ? C65 N61 1.367(9) . ? C65 H65 0.9500 . ? N1 O3 1.239(7) . ? N1 O2 1.248(7) . ? N1 O1 1.248(7) . ? N43 Mn1 2.252(5) . ? N63 Mn1 2.238(5) 3_556 ? O1 Mn1 2.269(4) . ? Mn1 N63 2.238(5) 5_676 ? Mn1 N63 2.238(5) 3_444 ? Mn1 N43 2.252(5) 7_565 ? Mn1 O1 2.269(4) 7_565 ? C2A O1A 1.257(17) . ? C2A N3A 1.330(16) . ? C2A H2A 0.9500 . ? C4A N3A 1.43(2) . ? C4A H4AA 0.9800 . ? C4A H4AB 0.9800 . ? C4A H4AC 0.9800 . ? C5A N3A 1.458(18) . ? C5A H5AA 0.9800 . ? C5A H5AB 0.9800 . ? C5A H5AC 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 C11 C19 120.5(6) . . ? C12 C11 C21 120.7(6) . . ? C19 C11 C21 118.8(6) . . ? C11 C12 C13 120.3(7) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 120.4(7) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C20 119.6(6) . . ? C13 C14 C26 119.7(6) . . ? C20 C14 C26 120.7(6) . . ? C16 C15 C20 120.6(6) . . ? C16 C15 C29 119.9(7) . . ? C20 C15 C29 119.5(6) . . ? C15 C16 C17 121.0(7) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C18 C17 C16 119.6(6) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 119.7(6) . . ? C17 C18 C24 119.6(6) . . ? C19 C18 C24 120.7(6) . . ? C20 C19 C18 120.8(6) . . ? C20 C19 C11 118.3(6) . . ? C18 C19 C11 120.9(6) . . ? C14 C20 C19 120.9(6) . . ? C14 C20 C15 121.0(6) . . ? C19 C20 C15 118.2(6) . . ? O22 C21 N23 119.7(6) . . ? O22 C21 C11 121.7(6) . . ? N23 C21 C11 118.5(6) . . ? O25 C24 N23 120.6(6) . . ? O25 C24 C18 122.9(7) . . ? N23 C24 C18 116.4(6) . . ? O27 C26 N28 119.9(6) . . ? O27 C26 C14 123.3(7) . . ? N28 C26 C14 116.8(6) . . ? O30 C29 N28 119.7(6) . . ? O30 C29 C15 122.8(6) . . ? N28 C29 C15 117.4(6) . . ? N23 C31 C32 113.6(5) . . ? N23 C31 H31A 108.8 . . ? C32 C31 H31A 108.8 . . ? N23 C31 H31B 108.8 . . ? C32 C31 H31B 108.8 . . ? H31A C31 H31B 107.7 . . ? C33 C32 C31 111.0(6) . . ? C33 C32 H32A 109.4 . . ? C31 C32 H32A 109.4 . . ? C33 C32 H32B 109.4 . . ? C31 C32 H32B 109.4 . . ? H32A C32 H32B 108.0 . . ? N41 C33 C32 111.4(6) . . ? N41 C33 H33A 109.3 . . ? C32 C33 H33A 109.3 . . ? N41 C33 H33B 109.3 . . ? C32 C33 H33B 109.3 . . ? H33A C33 H33B 108.0 . . ? N43 C42 N41 111.7(6) . . ? N43 C42 H42 124.1 . . ? N41 C42 H42 124.1 . . ? C45 C44 N43 109.3(6) . . ? C45 C44 H44 125.4 . . ? N43 C44 H44 125.4 . . ? C44 C45 N41 106.7(6) . . ? C44 C45 H45 126.7 . . ? N41 C45 H45 126.7 . . ? N28 C51 C52 112.5(5) . . ? N28 C51 H51A 109.1 . . ? C52 C51 H51A 109.1 . . ? N28 C51 H51B 109.1 . . ? C52 C51 H51B 109.1 . . ? H51A C51 H51B 107.8 . . ? C53 C52 C51 112.6(5) . . ? C53 C52 H52A 109.1 . . ? C51 C52 H52A 109.1 . . ? C53 C52 H52B 109.1 . . ? C51 C52 H52B 109.1 . . ? H52A C52 H52B 107.8 . . ? N61 C53 C52 112.8(5) . . ? N61 C53 H53A 109.0 . . ? C52 C53 H53A 109.0 . . ? N61 C53 H53B 109.0 . . ? C52 C53 H53B 109.0 . . ? H53A C53 H53B 107.8 . . ? N63 C62 N61 110.8(6) . . ? N63 C62 H62 124.6 . . ? N61 C62 H62 124.6 . . ? C65 C64 N63 110.7(6) . . ? C65 C64 H64 124.7 . . ? N63 C64 H64 124.7 . . ? C64 C65 N61 105.2(6) . . ? C64 C65 H65 127.4 . . ? N61 C65 H65 127.4 . . ? O3 N1 O2 119.8(6) . . ? O3 N1 O1 120.1(6) . . ? O2 N1 O1 120.0(6) . . ? C21 N23 C24 124.3(6) . . ? C21 N23 C31 119.0(6) . . ? C24 N23 C31 116.4(6) . . ? C29 N28 C26 124.5(6) . . ? C29 N28 C51 117.7(6) . . ? C26 N28 C51 117.7(5) . . ? C42 N41 C45 106.1(5) . . ? C42 N41 C33 125.7(6) . . ? C45 N41 C33 128.0(6) . . ? C42 N43 C44 106.2(6) . . ? C42 N43 Mn1 127.5(4) . . ? C44 N43 Mn1 126.0(4) . . ? C62 N61 C65 107.8(5) . . ? C62 N61 C53 124.7(6) . . ? C65 N61 C53 127.4(5) . . ? C62 N63 C64 105.5(5) . . ? C62 N63 Mn1 130.2(4) . 3_556 ? C64 N63 Mn1 124.4(4) . 3_556 ? N1 O1 Mn1 136.8(4) . . ? N63 Mn1 N63 180.0 5_676 3_444 ? N63 Mn1 N43 86.10(19) 5_676 . ? N63 Mn1 N43 93.90(19) 3_444 . ? N63 Mn1 N43 93.90(19) 5_676 7_565 ? N63 Mn1 N43 86.10(19) 3_444 7_565 ? N43 Mn1 N43 180.0(3) . 7_565 ? N63 Mn1 O1 94.76(18) 5_676 7_565 ? N63 Mn1 O1 85.24(18) 3_444 7_565 ? N43 Mn1 O1 83.79(18) . 7_565 ? N43 Mn1 O1 96.21(18) 7_565 7_565 ? N63 Mn1 O1 85.24(18) 5_676 . ? N63 Mn1 O1 94.76(18) 3_444 . ? N43 Mn1 O1 96.21(18) . . ? N43 Mn1 O1 83.79(18) 7_565 . ? O1 Mn1 O1 180.0(2) 7_565 . ? O1A C2A N3A 123.5(13) . . ? C2A N3A C4A 121.6(12) . . ? C2A N3A C5A 120.3(13) . . ? C4A N3A C5A 118.1(13) . . ? 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 C19 C11 C12 C13 1.0(9) . . . . ? C21 C11 C12 C13 -178.5(6) . . . . ? C11 C12 C13 C14 -0.5(9) . . . . ? C12 C13 C14 C20 0.1(9) . . . . ? C12 C13 C14 C26 -180.0(6) . . . . ? C20 C15 C16 C17 3.4(9) . . . . ? C29 C15 C16 C17 -177.1(5) . . . . ? C15 C16 C17 C18 -1.3(9) . . . . ? C16 C17 C18 C19 -1.7(9) . . . . ? C16 C17 C18 C24 179.6(5) . . . . ? C17 C18 C19 C20 2.6(9) . . . . ? C24 C18 C19 C20 -178.7(6) . . . . ? C17 C18 C19 C11 -177.5(6) . . . . ? C24 C18 C19 C11 1.2(9) . . . . ? C12 C11 C19 C20 -1.0(9) . . . . ? C21 C11 C19 C20 178.5(5) . . . . ? C12 C11 C19 C18 179.1(6) . . . . ? C21 C11 C19 C18 -1.4(9) . . . . ? C13 C14 C20 C19 -0.1(9) . . . . ? C26 C14 C20 C19 180.0(6) . . . . ? C13 C14 C20 C15 -179.1(6) . . . . ? C26 C14 C20 C15 1.0(9) . . . . ? C18 C19 C20 C14 -179.6(6) . . . . ? C11 C19 C20 C14 0.5(9) . . . . ? C18 C19 C20 C15 -0.5(8) . . . . ? C11 C19 C20 C15 179.5(6) . . . . ? C16 C15 C20 C14 176.6(6) . . . . ? C29 C15 C20 C14 -2.9(9) . . . . ? C16 C15 C20 C19 -2.4(9) . . . . ? C29 C15 C20 C19 178.1(5) . . . . ? C12 C11 C21 O22 -0.3(9) . . . . ? C19 C11 C21 O22 -179.8(6) . . . . ? C12 C11 C21 N23 177.0(6) . . . . ? C19 C11 C21 N23 -2.5(8) . . . . ? C17 C18 C24 O25 -1.0(9) . . . . ? C19 C18 C24 O25 -179.7(6) . . . . ? C17 C18 C24 N23 -178.4(6) . . . . ? C19 C18 C24 N23 2.9(8) . . . . ? C13 C14 C26 O27 1.8(9) . . . . ? C20 C14 C26 O27 -178.2(6) . . . . ? C13 C14 C26 N28 -177.2(6) . . . . ? C20 C14 C26 N28 2.8(8) . . . . ? C16 C15 C29 O30 4.0(9) . . . . ? C20 C15 C29 O30 -176.5(6) . . . . ? C16 C15 C29 N28 -178.5(5) . . . . ? C20 C15 C29 N28 1.0(8) . . . . ? N23 C31 C32 C33 -173.7(6) . . . . ? C31 C32 C33 N41 68.7(8) . . . . ? N43 C44 C45 N41 -0.2(7) . . . . ? N28 C51 C52 C53 -177.8(6) . . . . ? C51 C52 C53 N61 -55.4(8) . . . . ? N63 C64 C65 N61 0.0(8) . . . . ? O22 C21 N23 C24 -175.5(6) . . . . ? C11 C21 N23 C24 7.1(9) . . . . ? O22 C21 N23 C31 -1.8(8) . . . . ? C11 C21 N23 C31 -179.1(5) . . . . ? O25 C24 N23 C21 175.3(6) . . . . ? C18 C24 N23 C21 -7.2(9) . . . . ? O25 C24 N23 C31 1.4(9) . . . . ? C18 C24 N23 C31 178.9(5) . . . . ? C32 C31 N23 C21 -84.4(8) . . . . ? C32 C31 N23 C24 89.9(7) . . . . ? O30 C29 N28 C26 -179.4(5) . . . . ? C15 C29 N28 C26 3.0(8) . . . . ? O30 C29 N28 C51 -3.3(8) . . . . ? C15 C29 N28 C51 179.1(5) . . . . ? O27 C26 N28 C29 176.1(6) . . . . ? C14 C26 N28 C29 -4.8(8) . . . . ? O27 C26 N28 C51 0.0(8) . . . . ? C14 C26 N28 C51 179.1(5) . . . . ? C52 C51 N28 C29 -76.9(7) . . . . ? C52 C51 N28 C26 99.4(7) . . . . ? N43 C42 N41 C45 1.1(7) . . . . ? N43 C42 N41 C33 177.9(5) . . . . ? C44 C45 N41 C42 -0.5(7) . . . . ? C44 C45 N41 C33 -177.2(6) . . . . ? C32 C33 N41 C42 71.1(8) . . . . ? C32 C33 N41 C45 -112.9(7) . . . . ? N41 C42 N43 C44 -1.2(7) . . . . ? N41 C42 N43 Mn1 172.7(4) . . . . ? C45 C44 N43 C42 0.9(7) . . . . ? C45 C44 N43 Mn1 -173.2(4) . . . . ? N63 C62 N61 C65 0.3(8) . . . . ? N63 C62 N61 C53 179.1(6) . . . . ? C64 C65 N61 C62 -0.2(8) . . . . ? C64 C65 N61 C53 -178.9(6) . . . . ? C52 C53 N61 C62 141.9(7) . . . . ? C52 C53 N61 C65 -39.6(10) . . . . ? N61 C62 N63 C64 -0.3(7) . . . . ? N61 C62 N63 Mn1 178.9(4) . . . 3_556 ? C65 C64 N63 C62 0.2(8) . . . . ? C65 C64 N63 Mn1 -179.1(5) . . . 3_556 ? O3 N1 O1 Mn1 -13.7(10) . . . . ? O2 N1 O1 Mn1 163.2(5) . . . . ? C42 N43 Mn1 N63 -104.0(5) . . . 5_676 ? C44 N43 Mn1 N63 68.7(5) . . . 5_676 ? C42 N43 Mn1 N63 76.0(5) . . . 3_444 ? C44 N43 Mn1 N63 -111.3(5) . . . 3_444 ? C42 N43 Mn1 O1 160.7(5) . . . 7_565 ? C44 N43 Mn1 O1 -26.5(5) . . . 7_565 ? C42 N43 Mn1 O1 -19.3(5) . . . . ? C44 N43 Mn1 O1 153.5(5) . . . . ? N1 O1 Mn1 N63 134.7(6) . . . 5_676 ? N1 O1 Mn1 N63 -45.3(6) . . . 3_444 ? N1 O1 Mn1 N43 49.1(6) . . . . ? N1 O1 Mn1 N43 -130.9(6) . . . 7_565 ? O1A C2A N3A C4A 2(2) . . . . ? O1A C2A N3A C5A -176.9(13) . . . . ? #=== END OF CIF _database_code_depnum_ccdc_archive 'CCDC 942766'