# Electronic Supplementary Material (ESI) for Chemical Communications # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H27 N O2' _chemical_formula_weight 361.47 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 9.925(2) _cell_length_b 14.231(3) _cell_length_c 29.217(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4126.7 _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8794 _exptl_absorpt_correction_T_max 0.9562 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _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 'Bruker-Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38485 _diffrn_reflns_av_R_equivalents 0.2177 _diffrn_reflns_av_sigmaI/netI 0.1518 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 5.01 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4705 _reflns_number_gt 1945 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2002) ' _computing_cell_refinement 'DIRAX (Duisenberg,1992)' _computing_data_reduction 'EVAL (Nonius, 2002)' _computing_structure_solution 'SIR2011, updated version of SIR2008 (Burla et al., 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0839P)^2^+0.0000P] 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 4705 _refine_ls_number_parameters 260 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1974 _refine_ls_R_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.1818 _refine_ls_wR_factor_gt 0.1393 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.947 _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 O1 O 0.43471(17) 0.13716(11) 0.33897(5) 0.0466(5) Uani 1 1 d . . . O2 O 0.18600(19) 0.10154(14) 0.37188(8) 0.0734(7) Uani 1 1 d . . . N1 N 0.3933(2) 0.44079(13) 0.32700(8) 0.0574(7) Uani 1 1 d . . . C2 C 0.6567(2) 0.19782(16) 0.34002(9) 0.0408(6) Uani 1 1 d . . . C3 C 0.4905(2) 0.23735(15) 0.40370(8) 0.0395(6) Uani 1 1 d . . . C4 C 0.5417(2) 0.16200(16) 0.36971(8) 0.0401(6) Uani 1 1 d . . . C5 C 0.7432(3) 0.26757(18) 0.35451(10) 0.0571(8) Uani 1 1 d . . . H5 H 0.7273 0.2973 0.3823 0.069 Uiso 1 1 calc R . . C6 C 0.4168(2) 0.31693(16) 0.38934(8) 0.0434(6) Uani 1 1 d . . . C7 C 0.5868(3) 0.07332(15) 0.39621(8) 0.0423(7) Uani 1 1 d . . . C8 C 0.5132(3) 0.22752(17) 0.45046(9) 0.0546(7) Uani 1 1 d . . . H8 H 0.5638 0.1766 0.4606 0.066 Uiso 1 1 calc R . . C9 C 0.3866(3) 0.33990(16) 0.34013(9) 0.0489(7) Uani 1 1 d . . . H9 H 0.4412 0.3013 0.3195 0.059 Uiso 1 1 calc R . . C10 C 0.3672(3) 0.37772(18) 0.42246(10) 0.0571(8) Uani 1 1 d . . . H10 H 0.3171 0.4294 0.4130 0.069 Uiso 1 1 calc R . . C11 C 0.7204(3) 0.05372(18) 0.40524(9) 0.0540(7) Uani 1 1 d . . . H11 H 0.7871 0.0923 0.3931 0.065 Uiso 1 1 calc R . . C12 C 0.7568(3) -0.0224(2) 0.43203(10) 0.0619(8) Uani 1 1 d . . . H12 H 0.8473 -0.0344 0.4379 0.074 Uiso 1 1 calc R . . C13 C 0.6836(3) 0.15503(17) 0.29804(9) 0.0520(7) Uani 1 1 d . . . H13 H 0.6265 0.1082 0.2872 0.062 Uiso 1 1 calc R . . C14 C 0.4910(3) 0.01277(19) 0.41382(10) 0.0605(8) Uani 1 1 d . . . H14 H 0.4004 0.0230 0.4074 0.073 Uiso 1 1 calc R . . C15 C 0.3886(3) 0.3652(2) 0.46836(10) 0.0659(9) Uani 1 1 d . . . H15 H 0.3526 0.4068 0.4896 0.079 Uiso 1 1 calc R . . C16 C 0.7933(3) 0.1814(2) 0.27250(10) 0.0659(9) Uani 1 1 d . . . H16 H 0.8098 0.1523 0.2445 0.079 Uiso 1 1 calc R . . C17 C 0.8535(3) 0.2942(2) 0.32840(12) 0.0712(9) Uani 1 1 d . . . H17 H 0.9100 0.3420 0.3385 0.085 Uiso 1 1 calc R . . C18 C 0.4642(3) 0.28987(19) 0.48214(10) 0.0666(9) Uani 1 1 d . . . H18 H 0.4824 0.2810 0.5131 0.080 Uiso 1 1 calc R . . C19 C 0.5278(4) -0.06281(19) 0.44079(11) 0.0736(9) Uani 1 1 d . . . H19 H 0.4619 -0.1021 0.4528 0.088 Uiso 1 1 calc R . . C20 C 0.8789(3) 0.2501(2) 0.28775(13) 0.0698(9) Uani 1 1 d . . . H20 H 0.9540 0.2666 0.2705 0.084 Uiso 1 1 calc R . . C21 C 0.2355(3) 0.3421(2) 0.32419(11) 0.0729(9) Uani 1 1 d . . . H21A H 0.2092 0.2894 0.3052 0.088 Uiso 1 1 calc R . . H21B H 0.1713 0.3525 0.3487 0.088 Uiso 1 1 calc R . . C22 C 0.6603(4) -0.07998(19) 0.44984(10) 0.0660(8) Uani 1 1 d . . . H22 H 0.6848 -0.1307 0.4681 0.079 Uiso 1 1 calc R . . C23 C 0.1106(5) 0.1418(3) 0.40594(19) 0.1032(16) Uani 1 1 d . . . C24 C 0.2725(3) 0.42972(19) 0.29779(12) 0.0788(10) Uani 1 1 d . . . H24A H 0.2931 0.4181 0.2658 0.095 Uiso 1 1 calc R . . H24B H 0.2078 0.4803 0.3010 0.095 Uiso 1 1 calc R . . C25 C 0.5199(3) 0.4670(2) 0.30395(12) 0.0923(11) Uani 1 1 d . . . H25A H 0.5148 0.5313 0.2941 0.138 Uiso 1 1 calc R . . H25B H 0.5334 0.4271 0.2779 0.138 Uiso 1 1 calc R . . H25C H 0.5938 0.4597 0.3248 0.138 Uiso 1 1 calc R . . HO1 H 0.341(4) 0.132(2) 0.3565(14) 0.138 Uiso 1 1 d . . . HO2 H 0.157(4) 0.042(3) 0.3625(14) 0.138 Uiso 1 1 d . . . H23A H 0.080(4) 0.097(3) 0.4266(15) 0.138 Uiso 1 1 d . . . H23B H 0.156(4) 0.192(3) 0.4188(15) 0.138 Uiso 1 1 d . . . H23C H 0.038(4) 0.173(3) 0.3948(15) 0.138 Uiso 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 O1 0.0478(11) 0.0493(10) 0.0427(10) -0.0058(8) -0.0065(9) -0.0046(8) O2 0.0560(13) 0.0668(13) 0.0973(17) -0.0233(12) 0.0217(12) -0.0117(11) N1 0.0745(16) 0.0412(13) 0.0566(15) 0.0026(11) -0.0102(14) 0.0081(11) C2 0.0414(15) 0.0381(14) 0.0429(16) 0.0016(12) 0.0000(13) 0.0042(12) C3 0.0424(15) 0.0348(13) 0.0413(16) -0.0019(11) 0.0011(12) -0.0016(11) C4 0.0413(15) 0.0387(13) 0.0403(14) -0.0043(12) -0.0041(13) -0.0010(12) C5 0.0546(18) 0.0580(17) 0.0588(18) -0.0078(15) 0.0058(16) -0.0087(15) C6 0.0449(15) 0.0413(14) 0.0440(15) -0.0042(12) 0.0058(13) -0.0015(12) C7 0.0501(17) 0.0359(14) 0.0408(15) -0.0041(11) 0.0007(13) 0.0005(12) C8 0.074(2) 0.0466(15) 0.0430(17) -0.0021(13) -0.0017(15) 0.0025(13) C9 0.0567(17) 0.0427(15) 0.0473(16) -0.0035(12) -0.0010(14) 0.0081(12) C10 0.0656(19) 0.0441(15) 0.062(2) -0.0046(14) 0.0105(16) 0.0068(13) C11 0.0501(19) 0.0507(16) 0.0612(19) 0.0048(14) -0.0040(15) 0.0023(14) C12 0.0605(19) 0.0587(18) 0.067(2) -0.0003(16) -0.0070(16) 0.0140(16) C13 0.0603(18) 0.0480(15) 0.0475(17) -0.0022(13) 0.0060(15) 0.0046(13) C14 0.0541(18) 0.0534(17) 0.074(2) 0.0159(16) 0.0015(16) -0.0003(14) C15 0.094(2) 0.0534(18) 0.0500(19) -0.0120(15) 0.0197(17) 0.0052(16) C16 0.075(2) 0.072(2) 0.0502(19) 0.0073(16) 0.0191(18) 0.0143(18) C17 0.055(2) 0.073(2) 0.085(3) 0.0099(19) 0.0045(19) -0.0171(16) C18 0.104(2) 0.0558(18) 0.0398(16) -0.0029(15) 0.0079(17) -0.0013(17) C19 0.081(2) 0.0554(19) 0.085(2) 0.0241(17) 0.0046(19) -0.0044(17) C20 0.058(2) 0.081(2) 0.071(2) 0.0235(19) 0.0207(18) 0.0047(18) C21 0.063(2) 0.083(2) 0.073(2) -0.0114(18) -0.0088(17) 0.0004(17) C22 0.089(2) 0.0477(16) 0.061(2) 0.0062(15) -0.0018(19) 0.0138(18) C23 0.090(3) 0.078(3) 0.142(4) -0.026(3) 0.045(3) -0.008(2) C24 0.106(3) 0.0597(19) 0.071(2) -0.0049(17) -0.025(2) 0.0239(18) C25 0.107(3) 0.084(2) 0.086(3) 0.011(2) 0.034(2) -0.024(2) _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 O1 C4 1.435(3) . ? O2 C23 1.371(4) . ? N1 C25 1.473(3) . ? N1 C24 1.480(3) . ? N1 C9 1.488(3) . ? C2 C5 1.379(3) . ? C2 C13 1.395(3) . ? C2 C4 1.522(3) . ? C3 C8 1.392(3) . ? C3 C6 1.412(3) . ? C3 C4 1.547(3) . ? C4 C7 1.547(3) . ? C5 C17 1.387(4) . ? C6 C10 1.388(3) . ? C6 C9 1.505(3) . ? C7 C11 1.381(3) . ? C7 C14 1.382(3) . ? C8 C18 1.371(3) . ? C9 C21 1.571(4) . ? C10 C15 1.369(4) . ? C11 C12 1.385(4) . ? C12 C22 1.363(4) . ? C13 C16 1.373(4) . ? C14 C19 1.383(4) . ? C15 C18 1.369(4) . ? C16 C20 1.369(4) . ? C17 C20 1.367(4) . ? C19 C22 1.364(4) . ? C21 C24 1.512(4) . ? 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 C25 N1 C24 117.0(3) . . ? C25 N1 C9 113.6(2) . . ? C24 N1 C9 90.54(19) . . ? C5 C2 C13 117.7(2) . . ? C5 C2 C4 122.2(2) . . ? C13 C2 C4 119.9(2) . . ? C8 C3 C6 117.2(2) . . ? C8 C3 C4 120.5(2) . . ? C6 C3 C4 122.4(2) . . ? O1 C4 C2 106.31(19) . . ? O1 C4 C7 109.05(18) . . ? C2 C4 C7 109.95(19) . . ? O1 C4 C3 109.24(18) . . ? C2 C4 C3 112.34(18) . . ? C7 C4 C3 109.84(19) . . ? C2 C5 C17 121.3(3) . . ? C10 C6 C3 118.5(2) . . ? C10 C6 C9 117.4(2) . . ? C3 C6 C9 124.2(2) . . ? C11 C7 C14 117.6(2) . . ? C11 C7 C4 122.6(2) . . ? C14 C7 C4 119.7(2) . . ? C18 C8 C3 122.7(2) . . ? N1 C9 C6 116.6(2) . . ? N1 C9 C21 86.98(19) . . ? C6 C9 C21 118.6(2) . . ? C15 C10 C6 123.1(3) . . ? C7 C11 C12 121.1(3) . . ? C22 C12 C11 120.2(3) . . ? C16 C13 C2 120.7(3) . . ? C7 C14 C19 121.0(3) . . ? C18 C15 C10 118.4(3) . . ? C20 C16 C13 120.7(3) . . ? C20 C17 C5 119.8(3) . . ? C15 C18 C8 120.2(3) . . ? C22 C19 C14 120.3(3) . . ? C17 C20 C16 119.8(3) . . ? C24 C21 C9 86.3(2) . . ? C12 C22 C19 119.7(3) . . ? N1 C24 C21 89.5(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.251 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 969537' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H29 Ho0 N O3' _chemical_formula_weight 415.51 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' Ho Ho -0.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.246(2) _cell_length_b 6.725(5) _cell_length_c 14.229(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.04(11) _cell_angle_gamma 90.00 _cell_volume 1171.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 5.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8794 _exptl_absorpt_correction_T_max 0.9562 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _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 'Bruker-Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10833 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0451 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 5.15 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4939 _reflns_number_gt 3682 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2002)' _computing_cell_refinement 'DIRAX (Duisenberg,1992)' _computing_data_reduction 'EVAL (Nonius, 2002)' _computing_structure_solution 'SIR2011, updated version of SIR2008 (Burla et al., 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0537P)^2^+0.1257P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(10) _refine_ls_number_reflns 4939 _refine_ls_number_parameters 286 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1070 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration unk 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 O1 O 0.23165(12) 0.23916(18) 0.24011(10) 0.0474(3) Uani 1 1 d . . . O2 O 0.52031(10) 0.62497(19) 0.19924(9) 0.0500(3) Uani 1 1 d . . . N1 N 0.35675(12) 0.6157(2) 0.25809(11) 0.0402(3) Uani 1 1 d . . . O3 O 0.44809(12) 0.3270(2) 0.24233(11) 0.0563(4) Uani 1 1 d . . . C2 C 0.44266(14) 0.5083(3) 0.23370(12) 0.0410(4) Uani 1 1 d . . . C3 C 0.30319(14) 0.4834(3) 0.41282(13) 0.0402(4) Uani 1 1 d . . . C4 C 0.26287(14) 0.5603(2) 0.31668(13) 0.0377(4) Uani 1 1 d . . . C5 C 0.17954(14) 0.4248(2) 0.25996(13) 0.0380(4) Uani 1 1 d . . . C6 C 0.23418(16) 0.7894(2) 0.31633(14) 0.0448(4) Uani 1 1 d . . . H6A H 0.1642 0.8202 0.2856 0.054 Uiso 1 1 calc R . . H6B H 0.2405 0.8509 0.3780 0.054 Uiso 1 1 calc R . . C7 C 0.07688(15) 0.3741(3) 0.31280(14) 0.0435(4) Uani 1 1 d . . . C8 C 0.20962(18) 0.5043(3) 0.08761(14) 0.0532(5) Uani 1 1 d . . . H8 H 0.2701 0.4207 0.0909 0.064 Uiso 1 1 calc R . . C9 C 0.33219(17) 0.8294(3) 0.25479(15) 0.0485(5) Uani 1 1 d . . . H9A H 0.3122 0.8782 0.1924 0.058 Uiso 1 1 calc R . . H9B H 0.3883 0.9120 0.2848 0.058 Uiso 1 1 calc R . . C10 C 0.14607(16) 0.5262(3) 0.16551(14) 0.0434(4) Uani 1 1 d . . . C11 C 0.37404(17) 0.6021(3) 0.46698(15) 0.0522(5) Uani 1 1 d . . . H11 H 0.3967 0.7228 0.4425 0.063 Uiso 1 1 calc R . . C12 C 0.27422(17) 0.3009(3) 0.45114(15) 0.0541(5) Uani 1 1 d . . . H12 H 0.2286 0.2155 0.4166 0.065 Uiso 1 1 calc R . . C13 C 0.03740(17) 0.4893(4) 0.38484(16) 0.0575(5) Uani 1 1 d . . . H13 H 0.0747 0.6036 0.4040 0.069 Uiso 1 1 calc R . . C14 C 0.41187(19) 0.5472(4) 0.55577(17) 0.0633(6) Uani 1 1 d . . . H14 H 0.4588 0.6303 0.5903 0.076 Uiso 1 1 calc R . . C15 C 0.01837(18) 0.2052(3) 0.28500(16) 0.0552(5) Uani 1 1 d . . . H15 H 0.0429 0.1269 0.2362 0.066 Uiso 1 1 calc R . . C16 C 0.37946(19) 0.3682(4) 0.59269(17) 0.0703(7) Uani 1 1 d . . . H16 H 0.4028 0.3308 0.6531 0.084 Uiso 1 1 calc R . . C17 C 0.05366(18) 0.6452(3) 0.15681(17) 0.0581(5) Uani 1 1 d . . . H17 H 0.0082 0.6582 0.2074 0.070 Uiso 1 1 calc R . . C18 C 0.31233(19) 0.2453(4) 0.53948(17) 0.0700(7) Uani 1 1 d . . . H18 H 0.2923 0.1226 0.5635 0.084 Uiso 1 1 calc R . . C19 C 0.1843(2) 0.6051(4) 0.00502(17) 0.0685(7) Uani 1 1 d . . . H19 H 0.2289 0.5905 -0.0461 0.082 Uiso 1 1 calc R . . C20 C 0.6826(2) 0.4101(5) 0.21672(18) 0.0764(7) Uani 1 1 d . . . H20A H 0.6991 0.4840 0.2732 0.115 Uiso 1 1 calc R . . H20B H 0.7494 0.3752 0.1874 0.115 Uiso 1 1 calc R . . H20C H 0.6436 0.2912 0.2320 0.115 Uiso 1 1 calc R . . C21 C -0.0759(2) 0.1533(4) 0.3295(2) 0.0732(7) Uani 1 1 d . . . H21 H -0.1138 0.0392 0.3109 0.088 Uiso 1 1 calc R . . C22 C -0.0579(2) 0.4346(5) 0.42869(18) 0.0754(7) Uani 1 1 d . . . H22 H -0.0834 0.5122 0.4774 0.090 Uiso 1 1 calc R . . C23 C 0.61343(17) 0.5350(4) 0.15041(15) 0.0568(5) Uani 1 1 d . . . C24 C -0.1142(2) 0.2682(5) 0.4009(2) 0.0765(8) Uani 1 1 d . . . H24 H -0.1782 0.2331 0.4301 0.092 Uiso 1 1 calc R . . C25 C 0.5701(2) 0.4207(5) 0.06547(18) 0.0863(8) Uani 1 1 d . . . H25A H 0.5214 0.5039 0.0287 0.129 Uiso 1 1 calc R . . H25B H 0.5315 0.3051 0.0858 0.129 Uiso 1 1 calc R . . H25C H 0.6300 0.3806 0.0280 0.129 Uiso 1 1 calc R . . C26 C 0.0283(2) 0.7450(4) 0.0735(2) 0.0783(8) Uani 1 1 d . . . H26 H -0.0336 0.8251 0.0688 0.094 Uiso 1 1 calc R . . C27 C 0.0951(3) 0.7256(4) -0.00252(19) 0.0796(8) Uani 1 1 d . . . H27 H 0.0791 0.7940 -0.0581 0.096 Uiso 1 1 calc R . . C30 C 0.6741(2) 0.7212(5) 0.1204(2) 0.0954(9) Uani 1 1 d . . . H30A H 0.6263 0.8021 0.0815 0.143 Uiso 1 1 calc R . . H30B H 0.7366 0.6837 0.0856 0.143 Uiso 1 1 calc R . . H30C H 0.6976 0.7952 0.1752 0.143 Uiso 1 1 calc R . . HO1 H 0.307(3) 0.252(5) 0.243(2) 0.114 Uiso 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 O1 0.0443(8) 0.0251(6) 0.0729(9) -0.0033(5) 0.0039(7) 0.0050(5) O2 0.0397(7) 0.0462(8) 0.0648(9) 0.0016(6) 0.0124(6) -0.0016(6) N1 0.0375(8) 0.0252(7) 0.0582(9) 0.0038(6) 0.0066(7) 0.0033(6) O3 0.0460(9) 0.0341(8) 0.0894(10) 0.0016(7) 0.0120(7) 0.0091(6) C2 0.0365(10) 0.0368(10) 0.0496(10) 0.0004(7) 0.0025(8) 0.0012(8) C3 0.0302(9) 0.0381(9) 0.0526(10) 0.0003(7) 0.0065(8) 0.0055(7) C4 0.0317(9) 0.0272(8) 0.0544(10) 0.0005(7) 0.0047(8) 0.0034(6) C5 0.0363(9) 0.0242(8) 0.0534(10) 0.0008(7) 0.0024(8) 0.0050(7) C6 0.0433(11) 0.0258(9) 0.0653(12) -0.0054(7) 0.0002(9) 0.0048(7) C7 0.0325(10) 0.0425(11) 0.0553(11) 0.0094(8) -0.0018(8) 0.0026(7) C8 0.0572(13) 0.0457(11) 0.0568(12) -0.0043(9) -0.0001(10) -0.0067(10) C9 0.0505(12) 0.0253(9) 0.0697(13) 0.0018(8) 0.0007(10) 0.0018(8) C10 0.0441(11) 0.0308(9) 0.0552(11) -0.0010(8) -0.0010(9) -0.0034(8) C11 0.0421(11) 0.0534(12) 0.0611(12) -0.0004(9) 0.0024(9) -0.0043(9) C12 0.0447(12) 0.0491(12) 0.0682(13) 0.0139(10) -0.0036(10) -0.0017(9) C13 0.0411(11) 0.0654(14) 0.0664(13) -0.0030(10) 0.0060(10) 0.0000(10) C14 0.0427(12) 0.0847(17) 0.0620(13) -0.0055(12) -0.0046(10) -0.0013(11) C15 0.0452(12) 0.0479(12) 0.0723(13) 0.0105(10) -0.0023(10) -0.0072(9) C16 0.0472(14) 0.102(2) 0.0616(13) 0.0214(13) -0.0039(11) 0.0067(13) C17 0.0518(12) 0.0507(12) 0.0711(14) 0.0058(10) -0.0060(11) 0.0083(10) C18 0.0564(15) 0.0758(16) 0.0770(15) 0.0300(13) -0.0086(12) -0.0039(13) C19 0.0868(19) 0.0616(14) 0.0570(14) 0.0040(11) 0.0000(12) -0.0160(14) C20 0.0494(13) 0.110(2) 0.0697(15) 0.0034(14) 0.0043(11) 0.0223(14) C21 0.0498(14) 0.0675(16) 0.102(2) 0.0220(14) -0.0090(14) -0.0167(12) C22 0.0450(13) 0.110(2) 0.0714(15) 0.0023(14) 0.0113(11) 0.0054(14) C23 0.0394(11) 0.0776(15) 0.0541(12) 0.0011(10) 0.0098(9) 0.0066(10) C24 0.0393(13) 0.109(2) 0.0816(17) 0.0318(16) 0.0035(12) -0.0069(14) C25 0.0834(19) 0.115(2) 0.0602(15) -0.0164(15) -0.0005(13) 0.0172(18) C26 0.0785(18) 0.0612(15) 0.0935(19) 0.0235(13) -0.0219(15) 0.0107(13) C27 0.105(2) 0.0648(15) 0.0675(16) 0.0227(13) -0.0203(16) -0.0157(15) C30 0.0613(17) 0.118(2) 0.109(2) 0.0227(19) 0.0306(16) -0.0149(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 O1 C5 1.435(2) . ? O2 C2 1.339(2) . ? O2 C23 1.485(2) . ? N1 C2 1.332(2) . ? N1 C9 1.469(2) . ? N1 C4 1.491(2) . ? O3 C2 1.227(2) . ? C3 C11 1.391(3) . ? C3 C12 1.394(3) . ? C3 C4 1.528(3) . ? C4 C5 1.570(2) . ? C4 C6 1.581(2) . ? C5 C7 1.526(3) . ? C5 C10 1.549(3) . ? C6 C9 1.534(3) . ? C7 C13 1.385(3) . ? C7 C15 1.393(3) . ? C8 C19 1.382(3) . ? C8 C10 1.385(3) . ? C10 C17 1.388(3) . ? C11 C14 1.380(3) . ? C12 C18 1.377(3) . ? C13 C22 1.392(3) . ? C14 C16 1.378(4) . ? C15 C21 1.382(3) . ? C16 C18 1.374(4) . ? C17 C26 1.387(3) . ? C19 C27 1.362(4) . ? C20 C23 1.502(3) . ? C21 C24 1.372(4) . ? C22 C24 1.366(4) . ? C23 C25 1.512(3) . ? C23 C30 1.525(4) . ? C26 C27 1.386(4) . ? 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 O2 C23 119.98(15) . . ? C2 N1 C9 133.22(16) . . ? C2 N1 C4 129.92(14) . . ? C9 N1 C4 95.83(13) . . ? O3 C2 N1 123.58(18) . . ? O3 C2 O2 125.59(17) . . ? N1 C2 O2 110.83(15) . . ? C11 C3 C12 116.79(18) . . ? C11 C3 C4 118.50(16) . . ? C12 C3 C4 124.70(17) . . ? N1 C4 C3 110.74(14) . . ? N1 C4 C5 110.96(14) . . ? C3 C4 C5 116.58(14) . . ? N1 C4 C6 85.99(12) . . ? C3 C4 C6 113.41(15) . . ? C5 C4 C6 115.09(14) . . ? O1 C5 C7 106.42(13) . . ? O1 C5 C10 108.54(14) . . ? C7 C5 C10 109.18(14) . . ? O1 C5 C4 108.71(13) . . ? C7 C5 C4 114.09(14) . . ? C10 C5 C4 109.73(14) . . ? C9 C6 C4 89.67(13) . . ? C13 C7 C15 118.45(19) . . ? C13 C7 C5 123.71(17) . . ? C15 C7 C5 117.81(18) . . ? C19 C8 C10 120.9(2) . . ? N1 C9 C6 88.50(13) . . ? C8 C10 C17 118.00(19) . . ? C8 C10 C5 120.58(17) . . ? C17 C10 C5 121.39(18) . . ? C14 C11 C3 122.4(2) . . ? C18 C12 C3 120.9(2) . . ? C7 C13 C22 120.3(2) . . ? C16 C14 C11 119.4(2) . . ? C21 C15 C7 120.4(2) . . ? C18 C16 C14 119.4(2) . . ? C26 C17 C10 120.8(2) . . ? C16 C18 C12 121.1(2) . . ? C27 C19 C8 120.9(2) . . ? C24 C21 C15 120.7(2) . . ? C24 C22 C13 120.6(3) . . ? O2 C23 C20 111.05(16) . . ? O2 C23 C25 109.13(18) . . ? C20 C23 C25 113.1(2) . . ? O2 C23 C30 100.7(2) . . ? C20 C23 C30 111.4(2) . . ? C25 C23 C30 110.7(2) . . ? C22 C24 C21 119.6(2) . . ? C27 C26 C17 120.1(2) . . ? C19 C27 C26 119.3(2) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.156 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.032 _database_code_depnum_ccdc_archive 'CCDC 969538'