# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email m.k.whittlesey@bath.ac.uk _publ_contact_author_name M.Whittlesey loop_ _publ_author_name 'Madeeha Batool' 'Thomas Martin' 'Abu Naser' 'Michael W.George' 'Stuart Macgregor' 'Mary Mahon' M.Whittlesey data_c:\x-ray\helix\h07mkw03\maxus\h07mkw03 _database_code_depnum_ccdc_archive 'CCDC 690701' #TrackingRef '- h07mkw03.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H23 Mn N2 O2' _chemical_formula_weight 342.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.2920(2) _cell_length_b 9.0680(2) _cell_length_c 14.0950(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.209(1) _cell_angle_gamma 90.00 _cell_volume 1685.47(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 33606 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.103 _exptl_crystal_description Block _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.791 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 0.87 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15484 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 27.10 _reflns_number_total 3665 _reflns_number_gt 2612 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0641P)^2^+1.5396P] 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 SHELXL _refine_ls_extinction_coef 0.011(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3665 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1423 _refine_ls_wR_factor_gt 0.1174 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.02130(3) 0.36785(5) 0.68616(3) 0.0368(2) Uani 1 1 d . . . O1 O 0.0621(2) 0.6827(3) 0.7117(2) 0.0735(8) Uani 1 1 d . . . O2 O -0.18829(17) 0.4382(3) 0.61310(17) 0.0578(6) Uani 1 1 d . . . N1 N 0.07353(16) 0.3629(2) 0.90412(16) 0.0341(5) Uani 1 1 d . . . N2 N -0.06560(16) 0.2481(3) 0.86113(16) 0.0348(5) Uani 1 1 d . . . C1 C 0.0470(2) 0.5566(4) 0.7041(2) 0.0476(8) Uani 1 1 d . . . C2 C -0.1056(2) 0.4101(4) 0.6477(2) 0.0420(7) Uani 1 1 d . . . C3 C 0.0075(2) 0.3279(3) 0.82449(19) 0.0335(6) Uani 1 1 d . . . C4 C 0.0417(2) 0.3063(3) 0.9873(2) 0.0394(7) Uani 1 1 d . . . C5 C -0.0459(2) 0.2335(3) 0.9597(2) 0.0383(6) Uani 1 1 d . . . C6 C -0.1588(2) 0.1918(4) 0.8076(2) 0.0459(7) Uani 1 1 d . . . H6A H -0.1717 0.0909 0.8301 0.055 Uiso 1 1 calc R . . H6B H -0.1500 0.1857 0.7390 0.055 Uiso 1 1 calc R . . C7 C -0.2495(2) 0.2877(5) 0.8186(3) 0.0612(10) Uani 1 1 d . . . H7A H -0.2601 0.2914 0.8861 0.092 Uiso 1 1 calc R . . H7B H -0.3099 0.2464 0.7808 0.092 Uiso 1 1 calc R . . H7C H -0.2374 0.3876 0.7960 0.092 Uiso 1 1 calc R . . C8 C 0.1679(2) 0.4468(4) 0.9057(2) 0.0482(8) Uani 1 1 d . . . H8A H 0.1690 0.5254 0.9546 0.058 Uiso 1 1 calc R . . H8B H 0.1688 0.4952 0.8428 0.058 Uiso 1 1 calc R . . C9 C 0.2621(2) 0.3542(5) 0.9270(3) 0.0661(11) Uani 1 1 d . . . H9A H 0.2645 0.3116 0.9912 0.099 Uiso 1 1 calc R . . H9B H 0.3221 0.4160 0.9240 0.099 Uiso 1 1 calc R . . H9C H 0.2610 0.2747 0.8798 0.099 Uiso 1 1 calc R . . C10 C 0.0959(3) 0.3293(4) 1.0852(2) 0.0519(8) Uani 1 1 d . . . H10A H 0.0512 0.3025 1.1326 0.078 Uiso 1 1 calc R . . H10B H 0.1155 0.4332 1.0933 0.078 Uiso 1 1 calc R . . H10C H 0.1569 0.2674 1.0940 0.078 Uiso 1 1 calc R . . C11 C -0.1096(3) 0.1442(4) 1.0190(3) 0.0562(9) Uani 1 1 d . . . H11A H -0.0856 0.1590 1.0870 0.084 Uiso 1 1 calc R . . H11B H -0.1043 0.0395 1.0030 0.084 Uiso 1 1 calc R . . H11C H -0.1805 0.1757 1.0058 0.084 Uiso 1 1 calc R . . C12 C 0.1672(3) 0.2745(4) 0.6687(3) 0.0567(9) Uani 1 1 d . . . H12 H 0.2286 0.3012 0.7067 0.068 Uiso 1 1 calc R . . C13 C 0.1244(3) 0.3452(5) 0.5838(3) 0.0627(11) Uani 1 1 d . . . H13 H 0.1521 0.4276 0.5544 0.075 Uiso 1 1 calc R . . C14 C 0.0346(3) 0.2728(5) 0.5506(3) 0.0676(11) Uani 1 1 d . . . H14 H -0.0098 0.2977 0.4948 0.081 Uiso 1 1 calc R . . C15 C 0.0205(3) 0.1574(5) 0.6134(3) 0.0661(11) Uani 1 1 d . . . H15 H -0.0348 0.0903 0.6075 0.079 Uiso 1 1 calc R . . C16 C 0.1028(3) 0.1576(4) 0.6871(3) 0.0573(10) Uani 1 1 d . . . C17 C 0.1150(5) 0.0486(6) 0.7627(4) 0.1057(19) Uani 1 1 d . . . H17A H 0.1466 -0.0402 0.7400 0.159 Uiso 1 1 calc R . . H17B H 0.0485 0.0234 0.7813 0.159 Uiso 1 1 calc R . . H17C H 0.1583 0.0888 0.8181 0.159 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 0.0337(3) 0.0476(3) 0.0314(3) 0.00171(18) 0.01233(17) 0.00167(19) O1 0.093(2) 0.0509(15) 0.0773(19) 0.0091(14) 0.0119(16) -0.0187(15) O2 0.0421(12) 0.0753(17) 0.0557(14) 0.0045(12) 0.0050(11) 0.0116(12) N1 0.0292(11) 0.0412(13) 0.0329(12) 0.0002(10) 0.0082(9) -0.0018(10) N2 0.0331(12) 0.0402(13) 0.0329(12) 0.0000(10) 0.0106(9) -0.0039(10) C1 0.0478(17) 0.059(2) 0.0381(16) 0.0090(14) 0.0119(13) -0.0056(15) C2 0.0464(18) 0.0470(17) 0.0350(15) -0.0019(13) 0.0148(13) 0.0021(14) C3 0.0299(13) 0.0380(14) 0.0342(14) -0.0022(11) 0.0103(11) 0.0010(11) C4 0.0372(15) 0.0505(17) 0.0321(14) 0.0014(12) 0.0109(12) 0.0069(13) C5 0.0373(15) 0.0448(16) 0.0350(15) 0.0048(12) 0.0131(12) 0.0019(12) C6 0.0433(16) 0.0521(18) 0.0430(17) -0.0029(14) 0.0080(13) -0.0143(14) C7 0.0367(17) 0.095(3) 0.052(2) 0.0013(19) 0.0053(15) -0.0051(18) C8 0.0368(15) 0.060(2) 0.0473(18) 0.0026(15) 0.0051(13) -0.0118(14) C9 0.0314(16) 0.106(3) 0.061(2) 0.021(2) 0.0059(15) 0.0014(18) C10 0.0450(17) 0.077(2) 0.0339(16) 0.0012(15) 0.0057(13) 0.0055(16) C11 0.0545(19) 0.070(2) 0.0479(19) 0.0134(16) 0.0195(16) -0.0077(17) C12 0.0410(17) 0.081(3) 0.052(2) 0.0019(18) 0.0176(15) 0.0146(17) C13 0.062(2) 0.085(3) 0.049(2) 0.0150(18) 0.0361(18) 0.020(2) C14 0.063(2) 0.106(3) 0.0346(18) -0.0083(19) 0.0128(16) 0.026(2) C15 0.063(2) 0.073(3) 0.066(3) -0.030(2) 0.022(2) 0.0032(19) C16 0.071(2) 0.055(2) 0.052(2) 0.0011(16) 0.0300(18) 0.0217(18) C17 0.150(5) 0.085(4) 0.088(4) 0.014(3) 0.039(3) 0.041(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 C2 1.748(3) . ? Mn1 C1 1.757(4) . ? Mn1 C3 2.014(3) . ? Mn1 C13 2.121(3) . ? Mn1 C14 2.123(3) . ? Mn1 C12 2.158(3) . ? Mn1 C15 2.166(4) . ? Mn1 C16 2.192(3) . ? O1 C1 1.163(4) . ? O2 C2 1.173(4) . ? N1 C3 1.372(4) . ? N1 C4 1.393(4) . ? N1 C8 1.465(4) . ? N2 C3 1.364(3) . ? N2 C5 1.388(3) . ? N2 C6 1.460(4) . ? C4 C5 1.353(4) . ? C4 C10 1.489(4) . ? C5 C11 1.500(4) . ? C6 C7 1.510(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.507(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C16 1.407(5) . ? C12 C13 1.413(5) . ? C12 H12 0.9500 . ? C13 C14 1.390(6) . ? C13 H13 0.9500 . ? C14 C15 1.398(6) . ? C14 H14 0.9500 . ? C15 C16 1.410(6) . ? C15 H15 0.9500 . ? C16 C17 1.448(6) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 Mn1 C1 89.63(15) . . ? C2 Mn1 C3 97.97(12) . . ? C1 Mn1 C3 94.33(13) . . ? C2 Mn1 C13 119.36(14) . . ? C1 Mn1 C13 93.55(16) . . ? C3 Mn1 C13 141.85(13) . . ? C2 Mn1 C14 89.74(14) . . ? C1 Mn1 C14 119.22(17) . . ? C3 Mn1 C14 145.70(16) . . ? C13 Mn1 C14 38.25(16) . . ? C2 Mn1 C12 153.67(14) . . ? C1 Mn1 C12 103.73(15) . . ? C3 Mn1 C12 103.41(12) . . ? C13 Mn1 C12 38.56(14) . . ? C14 Mn1 C12 63.96(14) . . ? C2 Mn1 C15 95.70(15) . . ? C1 Mn1 C15 156.29(16) . . ? C3 Mn1 C15 107.71(15) . . ? C13 Mn1 C15 63.74(17) . . ? C14 Mn1 C15 38.04(16) . . ? C12 Mn1 C15 63.34(15) . . ? C2 Mn1 C16 130.48(16) . . ? C1 Mn1 C16 139.42(16) . . ? C3 Mn1 C16 86.71(12) . . ? C13 Mn1 C16 63.83(14) . . ? C14 Mn1 C16 63.61(15) . . ? C12 Mn1 C16 37.74(14) . . ? C15 Mn1 C16 37.74(15) . . ? C3 N1 C4 111.9(2) . . ? C3 N1 C8 126.2(2) . . ? C4 N1 C8 121.9(2) . . ? C3 N2 C5 112.1(2) . . ? C3 N2 C6 126.1(2) . . ? C5 N2 C6 121.7(2) . . ? O1 C1 Mn1 176.9(3) . . ? O2 C2 Mn1 173.6(3) . . ? N2 C3 N1 103.1(2) . . ? N2 C3 Mn1 128.1(2) . . ? N1 C3 Mn1 128.59(19) . . ? C5 C4 N1 106.2(2) . . ? C5 C4 C10 129.3(3) . . ? N1 C4 C10 124.4(3) . . ? C4 C5 N2 106.8(2) . . ? C4 C5 C11 129.0(3) . . ? N2 C5 C11 124.1(3) . . ? N2 C6 C7 112.5(3) . . ? N2 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? N2 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 C9 113.7(3) . . ? N1 C8 H8A 108.8 . . ? C9 C8 H8A 108.8 . . ? N1 C8 H8B 108.8 . . ? C9 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C16 C12 C13 107.9(3) . . ? C16 C12 Mn1 72.45(18) . . ? C13 C12 Mn1 69.31(18) . . ? C16 C12 H12 126.0 . . ? C13 C12 H12 126.0 . . ? Mn1 C12 H12 123.8 . . ? C14 C13 C12 107.9(4) . . ? C14 C13 Mn1 70.95(19) . . ? C12 C13 Mn1 72.13(18) . . ? C14 C13 H13 126.0 . . ? C12 C13 H13 126.0 . . ? Mn1 C13 H13 122.6 . . ? C13 C14 C15 108.5(3) . . ? C13 C14 Mn1 70.8(2) . . ? C15 C14 Mn1 72.6(2) . . ? C13 C14 H14 125.7 . . ? C15 C14 H14 125.7 . . ? Mn1 C14 H14 122.5 . . ? C14 C15 C16 108.2(4) . . ? C14 C15 Mn1 69.3(2) . . ? C16 C15 Mn1 72.1(2) . . ? C14 C15 H15 125.9 . . ? C16 C15 H15 125.9 . . ? Mn1 C15 H15 124.3 . . ? C12 C16 C15 107.4(3) . . ? C12 C16 C17 129.4(4) . . ? C15 C16 C17 123.1(4) . . ? C12 C16 Mn1 69.81(19) . . ? C15 C16 Mn1 70.1(2) . . ? C17 C16 Mn1 127.4(3) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.113 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.093