# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_2 _database_code_depnum_ccdc_archive 'CCDC 879340' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C55 H50 N5 O10' _chemical_formula_weight 941.00 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P2(1)/c 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 14.3345(8) _cell_length_b 9.0779(4) _cell_length_c 9.9141(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.758(6) _cell_angle_gamma 90.00 _cell_volume 1271.43(12) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour 0.3 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 495 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4670 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2214 _reflns_number_gt 1538 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+0.0461P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2214 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 C4 C 0.34225(10) 0.01942(16) 0.39840(16) 0.0485(4) Uani 1 1 d . . . O1 O 0.13701(9) 0.28231(16) 0.55521(15) 0.0829(5) Uani 1 1 d . . . C8 C 0.17402(11) 0.09801(18) 0.40361(17) 0.0546(4) Uani 1 1 d . . . H8A H 0.1628 0.1105 0.3050 0.066 Uiso 1 1 calc R . . H8B H 0.1598 -0.0036 0.4226 0.066 Uiso 1 1 calc R . . C11 C 0.00436(12) 0.18975(18) 0.40600(17) 0.0541(4) Uani 1 1 d . . . C7 C 0.27891(10) 0.12675(18) 0.45806(17) 0.0539(4) Uani 1 1 d . . . H7 H 0.2899 0.1146 0.5577 0.065 Uiso 1 1 calc R . . C9 C 0.10695(12) 0.19669(19) 0.46349(18) 0.0565(5) Uani 1 1 d . . . C1 C 0.45872(12) -0.17405(19) 0.2884(2) 0.0640(5) Uani 1 1 d . . . H1 H 0.4983 -0.2384 0.2518 0.077 Uiso 1 1 calc R . . C10 C 0.30459(12) 0.2789(2) 0.42637(19) 0.0595(5) Uani 1 1 d . . . C6 C 0.44401(13) -0.1913(2) 0.4198(2) 0.0686(5) Uani 1 1 d . . . H6 H 0.4732 -0.2685 0.4724 0.082 Uiso 1 1 calc R . . C3 C 0.35642(12) 0.03414(17) 0.26503(17) 0.0584(5) Uani 1 1 d . . . H3 H 0.3260 0.1096 0.2112 0.070 Uiso 1 1 calc R . . C5 C 0.38593(11) -0.0950(2) 0.47562(19) 0.0620(5) Uani 1 1 d . . . H5 H 0.3765 -0.1077 0.5654 0.074 Uiso 1 1 calc R . . C2 C 0.41442(13) -0.0604(2) 0.21030(19) 0.0671(5) Uani 1 1 d . . . H2 H 0.4239 -0.0480 0.1205 0.080 Uiso 1 1 calc R . . C16 C -0.05635(14) 0.2941(2) 0.4453(2) 0.0729(6) Uani 1 1 d . . . H16 H -0.0325 0.3659 0.5087 0.087 Uiso 1 1 calc R . . N1 N 0.32666(12) 0.3929(2) 0.39671(19) 0.0840(5) Uani 1 1 d . . . C12 C -0.03309(12) 0.0826(2) 0.31378(19) 0.0707(5) Uani 1 1 d . . . H12 H 0.0062 0.0106 0.2872 0.085 Uiso 1 1 calc R . . C15 C -0.15159(15) 0.2927(3) 0.3915(3) 0.0880(7) Uani 1 1 d . . . H15 H -0.1915 0.3636 0.4184 0.106 Uiso 1 1 calc R . . C13 C -0.12908(14) 0.0817(3) 0.2604(2) 0.0863(7) Uani 1 1 d . . . H13 H -0.1538 0.0090 0.1984 0.104 Uiso 1 1 calc R . . C14 C -0.18726(14) 0.1872(3) 0.2988(2) 0.0859(7) Uani 1 1 d . . . H14 H -0.2514 0.1872 0.2616 0.103 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 C4 0.0393(9) 0.0515(9) 0.0535(10) 0.0017(8) 0.0045(7) -0.0008(7) O1 0.0638(9) 0.0999(10) 0.0849(10) -0.0377(8) 0.0125(7) -0.0009(7) C8 0.0474(9) 0.0582(10) 0.0579(10) -0.0045(8) 0.0081(8) 0.0000(8) C11 0.0495(10) 0.0606(11) 0.0543(10) 0.0022(8) 0.0148(8) 0.0010(8) C7 0.0494(10) 0.0607(10) 0.0504(9) -0.0025(8) 0.0046(8) 0.0027(8) C9 0.0537(11) 0.0617(11) 0.0555(11) -0.0054(9) 0.0133(9) -0.0011(8) C1 0.0536(11) 0.0578(11) 0.0816(14) -0.0059(9) 0.0141(10) 0.0062(8) C10 0.0474(10) 0.0601(12) 0.0685(12) -0.0097(9) 0.0029(9) 0.0045(9) C6 0.0562(11) 0.0642(12) 0.0843(14) 0.0164(9) 0.0091(10) 0.0127(9) C3 0.0676(11) 0.0505(10) 0.0562(11) 0.0043(8) 0.0082(9) 0.0078(8) C5 0.0518(10) 0.0716(12) 0.0626(11) 0.0146(9) 0.0099(9) 0.0044(9) C2 0.0781(13) 0.0639(11) 0.0628(11) -0.0014(9) 0.0223(10) 0.0077(10) C16 0.0642(13) 0.0717(13) 0.0851(14) -0.0022(10) 0.0193(11) 0.0060(10) N1 0.0718(11) 0.0636(11) 0.1144(15) -0.0066(10) 0.0098(10) -0.0022(9) C12 0.0509(11) 0.0886(14) 0.0733(13) -0.0130(11) 0.0125(10) -0.0032(9) C15 0.0602(14) 0.1021(18) 0.1046(18) 0.0112(14) 0.0219(13) 0.0210(12) C13 0.0581(13) 0.1228(19) 0.0770(14) -0.0154(12) 0.0087(11) -0.0174(12) C14 0.0475(12) 0.132(2) 0.0781(15) 0.0199(14) 0.0095(11) 0.0042(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C4 C5 1.376(2) . ? C4 C3 1.378(2) . ? C4 C7 1.518(2) . ? O1 C9 1.2181(19) . ? C8 C9 1.508(2) . ? C8 C7 1.531(2) . ? C11 C12 1.380(2) . ? C11 C16 1.386(2) . ? C11 C9 1.486(2) . ? C7 C10 1.477(3) . ? C1 C6 1.363(3) . ? C1 C2 1.379(2) . ? C10 N1 1.136(2) . ? C6 C5 1.386(2) . ? C3 C2 1.370(2) . ? C16 C15 1.379(3) . ? C12 C13 1.388(3) . ? C15 C14 1.365(3) . ? C13 C14 1.366(3) . ? 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 C5 C4 C3 118.67(15) . . ? C5 C4 C7 120.88(15) . . ? C3 C4 C7 120.45(14) . . ? C9 C8 C7 114.43(13) . . ? C12 C11 C16 118.39(17) . . ? C12 C11 C9 122.19(15) . . ? C16 C11 C9 119.42(16) . . ? C10 C7 C4 109.27(14) . . ? C10 C7 C8 110.47(13) . . ? C4 C7 C8 111.69(13) . . ? O1 C9 C11 121.02(15) . . ? O1 C9 C8 120.31(15) . . ? C11 C9 C8 118.66(14) . . ? C6 C1 C2 119.45(17) . . ? N1 C10 C7 176.4(2) . . ? C1 C6 C5 120.66(16) . . ? C2 C3 C4 121.17(16) . . ? C4 C5 C6 120.09(17) . . ? C3 C2 C1 119.94(17) . . ? C15 C16 C11 120.9(2) . . ? C11 C12 C13 120.42(19) . . ? C14 C15 C16 120.0(2) . . ? C14 C13 C12 120.1(2) . . ? C15 C14 C13 120.2(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.104 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.030