# 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_1MeOH _audit_creation_date 2013-08-16T15:15:15-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C54 H58 N2 O10, 4(C H4 O)' _chemical_formula_sum 'C58 H74 N2 O14' _chemical_formula_weight 1023.19 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P b c n' _space_group_name_Hall '-P 2n 2ab' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 33.4782(19) _cell_length_b 9.1734(5) _cell_length_c 17.5749(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 5397.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 9907 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 29.08 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.259 _exptl_crystal_F_000 2192 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe X-ray _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bluker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_number 30513 _diffrn_reflns_limit_h_min -43 _diffrn_reflns_limit_h_max 45 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.302 _diffrn_reflns_theta_max 29.083 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.95 _reflns_number_total 6870 _reflns_number_gt 5673 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'SHELXS-2013 (Sheldrick, 2013)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 ; w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+3.4841P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 6870 _refine_ls_number_parameters 342 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.058 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1241 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.46 _refine_diff_density_min -0.34 _refine_diff_density_rms 0.049 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.04075(3) 0.16196(11) 0.30370(5) 0.0184(2) Uani 1 d . . O4 O 0.17200(3) 0.48143(11) 0.62107(5) 0.0205(2) Uani 1 d . . H4 H 0.1758 0.4568 0.6665 0.031 Uiso 1 calc . . O2 O -0.05849(3) 0.13116(10) 0.37563(5) 0.0165(2) Uani 1 d . . O5 O 0.21272(3) 0.61111(12) 0.73421(6) 0.0246(2) Uani 1 d . . H5A H 0.2236 0.6651 0.7668 0.037 Uiso 1 calc . . O3 O 0.18028(3) 0.63388(13) 0.40067(6) 0.0267(2) Uani 1 d . . C12 C -0.01950(4) 0.34610(15) 0.39845(7) 0.0148(2) Uani 1 d . . N1 N 0.13931(3) 0.51222(13) 0.48218(6) 0.0178(2) Uani 1 d . . H1 H 0.1338 0.5017 0.5308 0.021 Uiso 1 calc . . C3 C 0.07777(4) 0.38657(15) 0.46021(7) 0.0157(3) Uani 1 d . . H3 H 0.0696 0.418 0.5093 0.019 Uiso 1 calc . . O6 O 0.16586(4) 0.68268(14) 0.24617(6) 0.0360(3) Uani 1 d . . H6 H 0.1685 0.6607 0.2923 0.054 Uiso 1 calc . . C8 C 0.07845(4) 0.35671(15) 0.18293(7) 0.0151(3) Uani 1 d . . C14 C 0.01089(4) 0.25982(15) 0.44448(7) 0.0159(3) Uani 1 d . . H14A H 0.0081 0.2838 0.4991 0.019 Uiso 1 calc . . H14B H 0.006 0.1541 0.4381 0.019 Uiso 1 calc . . C7 C 0.11001(4) 0.27944(15) 0.23058(7) 0.0163(3) Uani 1 d . . H7A H 0.1098 0.1738 0.2192 0.02 Uiso 1 calc . . H7B H 0.1368 0.3183 0.2181 0.02 Uiso 1 calc . . C2 C 0.05277(4) 0.29654(14) 0.41793(7) 0.0149(2) Uani 1 d . . C5 C 0.12596(4) 0.39252(15) 0.35799(7) 0.0157(3) Uani 1 d . . H5 H 0.1506 0.4263 0.3377 0.019 Uiso 1 calc . . C6 C 0.10103(4) 0.30398(15) 0.31430(7) 0.0149(2) Uani 1 d . . C4 C 0.11462(4) 0.43130(14) 0.43159(7) 0.0154(3) Uani 1 d . . C13 C -0.05253(4) 0.27923(14) 0.36477(7) 0.0136(2) Uani 1 d . . C9 C 0.07255(4) 0.50591(16) 0.19213(8) 0.0193(3) Uani 1 d . . H9 H 0.0908 0.5609 0.222 0.023 Uiso 1 calc . . C16 C 0.19117(4) 0.60885(15) 0.60705(7) 0.0166(3) Uani 1 d . . C17 C 0.21250(4) 0.68024(16) 0.66538(8) 0.0196(3) Uani 1 d . . C33 C 0.16981(4) 0.60210(15) 0.46658(7) 0.0174(3) Uani 1 d . . C11 C -0.01366(4) 0.49428(15) 0.38542(8) 0.0184(3) Uani 1 d . . H11 H 0.009 0.5412 0.4067 0.022 Uiso 1 calc . . C10 C 0.04035(4) 0.57487(15) 0.15806(8) 0.0206(3) Uani 1 d . . H10 H 0.0365 0.6768 0.1644 0.025 Uiso 1 calc . . C1 C 0.06562(4) 0.25092(14) 0.34599(7) 0.0149(2) Uani 1 d . . C20 C 0.21041(5) 0.80073(17) 0.52053(9) 0.0256(3) Uani 1 d . . H20 H 0.2103 0.8419 0.4709 0.031 Uiso 1 calc . . C21 C 0.05416(5) 0.01326(17) 0.29760(9) 0.0261(3) Uani 1 d . . H21A H 0.0832 0.0128 0.287 0.031 Uiso 1 calc . . H21B H 0.0405 -0.0335 0.254 0.031 Uiso 1 calc . . C22 C 0.04628(5) -0.07516(17) 0.36838(9) 0.0274(3) Uani 1 d . . H22A H 0.0171 -0.0855 0.3758 0.033 Uiso 1 calc . . H22B H 0.0573 -0.0236 0.4132 0.033 Uiso 1 calc . . C18 C 0.23144(4) 0.81110(18) 0.65111(9) 0.0269(3) Uani 1 d . . H18 H 0.2453 0.8597 0.6909 0.032 Uiso 1 calc . . C24 C -0.09094(4) 0.10007(16) 0.42658(8) 0.0223(3) Uani 1 d . . H24A H -0.1153 0.1526 0.4101 0.027 Uiso 1 calc . . H24B H -0.0841 0.1324 0.4787 0.027 Uiso 1 calc . . C19 C 0.23027(5) 0.87183(19) 0.57868(10) 0.0317(4) Uani 1 d . . H19 H 0.2431 0.9623 0.5691 0.038 Uiso 1 calc . . C15 C 0.19054(4) 0.66910(16) 0.53376(8) 0.0175(3) Uani 1 d . . C25 C -0.09830(5) -0.06217(18) 0.42573(11) 0.0327(4) Uani 1 d . . H25A H -0.0744 -0.1133 0.4457 0.039 Uiso 1 calc . . H25B H -0.1027 -0.0948 0.3727 0.039 Uiso 1 calc . . C23 C 0.06531(6) -0.22614(18) 0.36226(11) 0.0369(4) Uani 1 d . . H23A H 0.0527 -0.2804 0.3207 0.055 Uiso 1 calc . . H23B H 0.0615 -0.279 0.4102 0.055 Uiso 1 calc . . H23C H 0.0939 -0.2159 0.352 0.055 Uiso 1 calc . . C27 C 0.17381(6) 0.8324(2) 0.23628(12) 0.0407(4) Uani 1 d . . H27A H 0.1518 0.8898 0.2578 0.061 Uiso 1 calc . . H27B H 0.1763 0.854 0.1819 0.061 Uiso 1 calc . . H27C H 0.1988 0.8577 0.2623 0.061 Uiso 1 calc . . C26 C -0.13448(5) -0.1021(2) 0.47374(14) 0.0462(5) Uani 1 d . . H26A H -0.1292 -0.078 0.5271 0.069 Uiso 1 calc . . H26B H -0.1397 -0.2068 0.4691 0.069 Uiso 1 calc . . H26C H -0.1578 -0.0473 0.4559 0.069 Uiso 1 calc . . O7 O 0.24409(3) 0.22576(16) 0.34673(7) 0.0369(3) Uani 1 d . . H7 H 0.2671 0.2038 0.3619 0.055 Uiso 1 calc . . C28 C 0.21553(6) 0.1491(3) 0.38961(14) 0.0579(7) Uani 1 d . . H28A H 0.2164 0.1823 0.4426 0.087 Uiso 1 calc . . H28B H 0.2214 0.0445 0.3876 0.087 Uiso 1 calc . . H28C H 0.1889 0.167 0.3686 0.087 Uiso 1 calc . . 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 0.0160(4) 0.0223(5) 0.0168(5) -0.0034(4) -0.0031(4) -0.0043(4) O4 0.0228(5) 0.0249(5) 0.0139(4) 0.0007(4) -0.0031(4) -0.0054(4) O2 0.0144(4) 0.0172(5) 0.0178(4) 0.0023(4) 0.0003(3) -0.0017(4) O5 0.0229(5) 0.0353(6) 0.0154(5) -0.0051(4) -0.0051(4) -0.0027(4) O3 0.0259(5) 0.0390(6) 0.0152(5) 0.0022(4) -0.0014(4) -0.0141(5) C12 0.0136(6) 0.0203(6) 0.0106(5) -0.0009(5) 0.0021(4) 0.0004(5) N1 0.0172(5) 0.0244(6) 0.0117(5) -0.0022(4) -0.0009(4) -0.0052(5) C3 0.0153(6) 0.0198(6) 0.0120(6) -0.0004(5) -0.0011(4) -0.0005(5) O6 0.0547(8) 0.0352(7) 0.0180(5) -0.0011(5) -0.0040(5) -0.0040(6) C8 0.0119(5) 0.0215(7) 0.0119(6) -0.0008(5) 0.0009(4) 0.0002(5) C14 0.0125(6) 0.0221(7) 0.0131(6) 0.0015(5) -0.0006(4) -0.0018(5) C7 0.0122(5) 0.0233(7) 0.0134(6) -0.0026(5) -0.0006(5) 0.0002(5) C2 0.0121(5) 0.0182(6) 0.0144(6) 0.0018(5) -0.0011(4) -0.0004(5) C5 0.0122(5) 0.0202(6) 0.0149(6) 0.0009(5) -0.0009(5) -0.0014(5) C6 0.0142(6) 0.0182(6) 0.0125(6) -0.0007(5) -0.0014(5) 0.0016(5) C4 0.0141(6) 0.0177(6) 0.0145(6) 0.0001(5) -0.0038(5) -0.0019(5) C13 0.0133(6) 0.0162(6) 0.0114(5) 0.0000(4) 0.0029(4) -0.0005(5) C9 0.0191(6) 0.0220(7) 0.0169(6) -0.0036(5) 0.0009(5) -0.0031(5) C16 0.0117(5) 0.0213(7) 0.0168(6) -0.0041(5) -0.0004(5) 0.0003(5) C17 0.0135(6) 0.0283(7) 0.0170(6) -0.0055(5) -0.0013(5) 0.0006(5) C33 0.0152(6) 0.0214(7) 0.0155(6) -0.0012(5) -0.0025(5) -0.0016(5) C11 0.0167(6) 0.0209(7) 0.0176(6) -0.0028(5) 0.0012(5) -0.0030(5) C10 0.0237(7) 0.0168(6) 0.0213(7) -0.0007(5) 0.0026(5) 0.0008(5) C1 0.0131(6) 0.0177(6) 0.0138(6) -0.0002(5) -0.0042(4) -0.0007(5) C20 0.0256(7) 0.0287(8) 0.0224(7) 0.0011(6) -0.0030(6) -0.0086(6) C21 0.0312(8) 0.0230(7) 0.0242(7) -0.0052(6) 0.0025(6) -0.0060(6) C22 0.0314(8) 0.0254(8) 0.0253(7) -0.0022(6) 0.0021(6) -0.0031(6) C18 0.0228(7) 0.0324(8) 0.0256(7) -0.0091(6) -0.0055(6) -0.0066(6) C24 0.0214(7) 0.0267(7) 0.0188(6) 0.0064(5) 0.0031(5) -0.0017(6) C19 0.0321(8) 0.0304(8) 0.0326(8) -0.0016(7) -0.0049(7) -0.0142(7) C15 0.0136(6) 0.0224(7) 0.0166(6) -0.0027(5) -0.0011(5) -0.0025(5) C25 0.0239(7) 0.0264(8) 0.0477(10) 0.0154(7) 0.0037(7) -0.0008(6) C23 0.0444(10) 0.0223(8) 0.0440(10) -0.0005(7) 0.0068(8) -0.0025(7) C27 0.0395(10) 0.0376(10) 0.0449(11) 0.0061(8) -0.0016(8) 0.0080(8) C26 0.0284(9) 0.0400(10) 0.0703(14) 0.0281(10) 0.0090(9) -0.0023(8) O7 0.0236(6) 0.0584(8) 0.0287(6) 0.0197(6) -0.0014(5) 0.0081(6) C28 0.0360(10) 0.0776(17) 0.0600(14) 0.0379(12) -0.0035(10) -0.0072(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 1.3827(15) . ? O1 C21 1.4402(18) . ? O4 C16 1.3559(17) . ? O4 H4 0.84 . ? O2 C13 1.3860(16) . ? O2 C24 1.4365(16) . ? O5 C17 1.3658(18) . ? O5 H5A 0.84 . ? O3 C33 1.2449(17) . ? C12 C11 1.3923(19) . ? C12 C13 1.3962(17) . ? C12 C14 1.5220(18) . ? N1 C33 1.3406(17) . ? N1 C4 1.4230(16) . ? N1 H1 0.88 . ? C3 C2 1.3910(18) . ? C3 C4 1.3938(18) . ? C3 H3 0.95 . ? O6 C27 1.410(2) . ? O6 H6 0.84 . ? C8 C9 1.3922(19) . ? C8 C13 1.4002(18) 3 ? C8 C7 1.5232(18) . ? C14 C2 1.5155(17) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C7 C6 1.5185(17) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C2 C1 1.3996(18) . ? C5 C4 1.3942(18) . ? C5 C6 1.3948(18) . ? C5 H5 0.95 . ? C6 C1 1.3972(18) . ? C13 C8 1.4002(18) 3 ? C9 C10 1.386(2) . ? C9 H9 0.95 . ? C16 C15 1.4019(19) . ? C16 C17 1.4105(18) . ? C17 C18 1.381(2) . ? C33 C15 1.5011(18) . ? C11 C10 1.389(2) 3 ? C11 H11 0.95 . ? C10 C11 1.389(2) 3 ? C10 H10 0.95 . ? C20 C19 1.383(2) . ? C20 C15 1.398(2) . ? C20 H20 0.95 . ? C21 C22 1.508(2) . ? C21 H21A 0.99 . ? C21 H21B 0.99 . ? C22 C23 1.528(2) . ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? C18 C19 1.390(2) . ? C18 H18 0.95 . ? C24 C25 1.509(2) . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? C19 H19 0.95 . ? C25 C26 1.521(2) . ? C25 H25A 0.99 . ? C25 H25B 0.99 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? C27 H27A 0.98 . ? C27 H27B 0.98 . ? C27 H27C 0.98 . ? C26 H26A 0.98 . ? C26 H26B 0.98 . ? C26 H26C 0.98 . ? O7 C28 1.406(2) . ? O7 H7 0.84 . ? C28 H28A 0.98 . ? C28 H28B 0.98 . ? C28 H28C 0.98 . ? 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 C1 O1 C21 114.28(10) . . ? C16 O4 H4 109.5 . . ? C13 O2 C24 112.90(10) . . ? C17 O5 H5A 109.5 . . ? C11 C12 C13 118.07(12) . . ? C11 C12 C14 120.08(12) . . ? C13 C12 C14 121.76(12) . . ? C33 N1 C4 129.46(11) . . ? C33 N1 H1 115.3 . . ? C4 N1 H1 115.3 . . ? C2 C3 C4 120.97(12) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C27 O6 H6 109.5 . . ? C9 C8 C13 118.74(12) . 3 ? C9 C8 C7 119.47(12) . . ? C13 C8 C7 121.51(12) 3 . ? C2 C14 C12 109.84(10) . . ? C2 C14 H14A 109.7 . . ? C12 C14 H14A 109.7 . . ? C2 C14 H14B 109.7 . . ? C12 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C6 C7 C8 109.06(10) . . ? C6 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? C6 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C3 C2 C1 118.37(11) . . ? C3 C2 C14 121.61(12) . . ? C1 C2 C14 119.74(11) . . ? C4 C5 C6 119.76(12) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 119.41(12) . . ? C5 C6 C7 120.09(12) . . ? C1 C6 C7 120.16(11) . . ? C3 C4 C5 120.04(12) . . ? C3 C4 N1 116.25(11) . . ? C5 C4 N1 123.68(12) . . ? O2 C13 C12 119.08(11) . . ? O2 C13 C8 119.39(11) . 3 ? C12 C13 C8 121.43(12) . 3 ? C10 C9 C8 120.58(13) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? O4 C16 C15 119.98(11) . . ? O4 C16 C17 120.51(12) . . ? C15 C16 C17 119.49(13) . . ? O5 C17 C18 124.20(13) . . ? O5 C17 C16 115.52(13) . . ? C18 C17 C16 120.28(13) . . ? O3 C33 N1 123.29(12) . . ? O3 C33 C15 120.37(12) . . ? N1 C33 C15 116.31(12) . . ? C10 C11 C12 121.32(13) 3 . ? C10 C11 H11 119.3 3 . ? C12 C11 H11 119.3 . . ? C9 C10 C11 119.68(13) . 3 ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 3 . ? O1 C1 C6 120.15(11) . . ? O1 C1 C2 118.48(11) . . ? C6 C1 C2 121.11(12) . . ? C19 C20 C15 120.89(14) . . ? C19 C20 H20 119.6 . . ? C15 C20 H20 119.6 . . ? O1 C21 C22 113.17(12) . . ? O1 C21 H21A 108.9 . . ? C22 C21 H21A 108.9 . . ? O1 C21 H21B 108.9 . . ? C22 C21 H21B 108.9 . . ? H21A C21 H21B 107.8 . . ? C21 C22 C23 110.88(14) . . ? C21 C22 H22A 109.5 . . ? C23 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 108.1 . . ? C17 C18 C19 120.12(13) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? O2 C24 C25 108.25(12) . . ? O2 C24 H24A 110 . . ? C25 C24 H24A 110 . . ? O2 C24 H24B 110 . . ? C25 C24 H24B 110 . . ? H24A C24 H24B 108.4 . . ? C20 C19 C18 120.09(15) . . ? C20 C19 H19 120 . . ? C18 C19 H19 120 . . ? C20 C15 C16 119.09(12) . . ? C20 C15 C33 116.29(12) . . ? C16 C15 C33 124.62(12) . . ? C24 C25 C26 111.25(15) . . ? C24 C25 H25A 109.4 . . ? C26 C25 H25A 109.4 . . ? C24 C25 H25B 109.4 . . ? C26 C25 H25B 109.4 . . ? H25A C25 H25B 108 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O6 C27 H27A 109.5 . . ? O6 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O6 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 O7 H7 109.5 . . ? O7 C28 H28A 109.5 . . ? O7 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O7 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 956152' ####################################################################### # # 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_1EtOH _audit_creation_date 2013-05-14T11:14:04-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C54 H58 N2 O10, 4(C2 H6 O)' _chemical_formula_sum 'C62 H82 N2 O14' _chemical_formula_weight 1079.30 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'C 2/c' _space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z+1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 34.399(4) _cell_length_b 9.4442(11) _cell_length_c 17.646(2) _cell_angle_alpha 90 _cell_angle_beta 95.3700(10) _cell_angle_gamma 90 _cell_volume 5707.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3926 _cell_measurement_theta_min 2.237 _cell_measurement_theta_max 28.242 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.256 _exptl_crystal_F_000 2320 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe X-ray _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bluker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_number 16077 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 45 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.237 _diffrn_reflns_theta_max 28.242 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.962 _reflns_number_total 6802 _reflns_number_gt 4694 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'SHELXS-2013 (Sheldrick, 2013)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 ; w=1/[\s^2^(Fo^2^)+(0.0469P)^2^+3.1958P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 6802 _refine_ls_number_parameters 360 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0777 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1172 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_restrained_S_all 1.02 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.312 _refine_diff_density_min -0.25 _refine_diff_density_rms 0.046 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.05769(3) 0.13372(11) 0.38375(6) 0.0210(2) Uani 1 d . . C13 C 0.05207(4) 0.27780(16) 0.37161(8) 0.0186(3) Uani 1 d . . C11 C 0.07064(5) 0.49617(18) 0.31622(9) 0.0242(4) Uani 1 d . . H11 H 0.0878 0.5488 0.2879 0.029 Uiso 1 calc . . C12 C 0.07674(4) 0.35145(17) 0.32712(8) 0.0196(3) Uani 1 d . . C10 C 0.03998(5) 0.56399(18) 0.34607(10) 0.0267(4) Uani 1 d . . H10 H 0.0363 0.6629 0.3389 0.032 Uiso 1 calc . . C25 C 0.08846(5) 0.10329(18) 0.44199(9) 0.0267(4) Uani 1 d . . H25A H 0.0818 0.1411 0.4915 0.032 Uiso 1 calc . . H25B H 0.1131 0.1482 0.4295 0.032 Uiso 1 calc . . C9 C 0.01459(5) 0.48689(17) 0.38660(9) 0.0239(4) Uani 1 d . . H9 H -0.0072 0.533 0.405 0.029 Uiso 1 calc . . C26 C 0.09337(5) -0.05445(19) 0.44667(12) 0.0359(4) Uani 1 d . . H26A H 0.0976 -0.0919 0.3957 0.043 Uiso 1 calc . . H26B H 0.0692 -0.0975 0.4625 0.043 Uiso 1 calc . . C27 C 0.12748(6) -0.0960(2) 0.50267(15) 0.0561(7) Uani 1 d . . H27A H 0.1511 -0.0473 0.4896 0.084 Uiso 1 calc . . H27B H 0.1315 -0.1986 0.5005 0.084 Uiso 1 calc . . H27C H 0.122 -0.0691 0.5542 0.084 Uiso 1 calc . . O6 O 0.82080(4) 0.33121(13) 0.71645(6) 0.0298(3) Uani 1 d . . H6A H 0.8262 0.3501 0.7627 0.045 Uiso 1 calc . . O7 O 0.76035(4) 0.81034(15) 0.78256(7) 0.0367(3) Uani 1 d . . H7 H 0.7361 0.816 0.785 0.055 Uiso 1 calc . . C8 C 0.02043(4) 0.34331(17) 0.40086(8) 0.0197(3) Uani 1 d . . C29 C 0.83943(6) 0.2019(2) 0.69858(11) 0.0365(4) Uani 1 d . . H29A H 0.8681 0.2148 0.7058 0.044 Uiso 1 calc . . H29B H 0.8323 0.1786 0.6444 0.044 Uiso 1 calc . . C28 C 0.82815(6) 0.0803(2) 0.74715(13) 0.0440(5) Uani 1 d . . H28A H 0.7997 0.0703 0.7424 0.066 Uiso 1 calc . . H28B H 0.8374 0.0987 0.8004 0.066 Uiso 1 calc . . H28C H 0.84 -0.0072 0.7303 0.066 Uiso 1 calc . . C31 C 0.78000(6) 0.8252(2) 0.85678(11) 0.0377(5) Uani 1 d . . H31A H 0.771 0.9132 0.8802 0.045 Uiso 1 calc . . H31B H 0.8084 0.8342 0.8526 0.045 Uiso 1 calc . . C30 C 0.77296(7) 0.7031(3) 0.90698(13) 0.0537(6) Uani 1 d . . H30A H 0.745 0.6966 0.9134 0.081 Uiso 1 calc . . H30B H 0.7877 0.7166 0.9568 0.081 Uiso 1 calc . . H30C H 0.7816 0.6155 0.8838 0.081 Uiso 1 calc . . O1 O 0.03897(3) 0.16117(12) 0.20108(6) 0.0238(3) Uani 1 d . . O3 O 0.16688(4) 0.63933(14) 0.13046(7) 0.0372(3) Uani 1 d . . O5 O 0.20941(3) 0.63099(13) -0.18837(6) 0.0298(3) Uani 1 d . . H5 H 0.2209 0.6851 -0.2168 0.045 Uiso 1 calc . . O4 O 0.17057(3) 0.48978(12) -0.08933(6) 0.0265(3) Uani 1 d . . H4 H 0.1759 0.4704 -0.1336 0.04 Uiso 1 calc . . N1 N 0.13391(4) 0.50476(15) 0.04000(7) 0.0230(3) Uani 1 d . . H1 H 0.131 0.4877 -0.0092 0.028 Uiso 1 calc . . C16 C 0.18116(4) 0.67541(17) 0.00314(9) 0.0216(3) Uani 1 d . . C5 C 0.04989(4) 0.29332(17) 0.08963(9) 0.0204(3) Uani 1 d . . C6 C 0.07395(4) 0.38133(17) 0.05169(9) 0.0213(3) Uani 1 d . . H6 H 0.0655 0.4128 0.0017 0.026 Uiso 1 calc . . C7 C 0.00863(4) 0.26002(18) 0.05712(9) 0.0217(3) Uani 1 d . . H7A H 0.0036 0.1574 0.062 0.026 Uiso 1 calc . . H7B H 0.0054 0.2847 0.0024 0.026 Uiso 1 calc . . C21 C 0.18544(4) 0.61949(17) -0.06880(9) 0.0208(3) Uani 1 d . . C2 C 0.12175(4) 0.38552(17) 0.16024(9) 0.0210(3) Uani 1 d . . H2 H 0.146 0.4183 0.1843 0.025 Uiso 1 calc . . C4 C 0.06303(4) 0.24763(17) 0.16279(9) 0.0200(3) Uani 1 d . . C3 C 0.09785(4) 0.29857(17) 0.19988(9) 0.0197(3) Uani 1 d . . C17 C 0.19750(5) 0.80748(18) 0.02213(10) 0.0256(4) Uani 1 d . . H17 H 0.1953 0.8456 0.0714 0.031 Uiso 1 calc . . C14 C 0.10707(4) 0.27526(18) 0.28474(9) 0.0213(3) Uani 1 d . . H14A H 0.1334 0.3124 0.3012 0.026 Uiso 1 calc . . H14B H 0.1067 0.1727 0.2963 0.026 Uiso 1 calc . . C1 C 0.11012(4) 0.42416(17) 0.08557(9) 0.0213(3) Uani 1 d . . C20 C 0.20589(4) 0.69664(19) -0.12060(9) 0.0241(4) Uani 1 d . . C19 C 0.22112(5) 0.82793(19) -0.10099(10) 0.0278(4) Uani 1 d . . H19 H 0.2346 0.8803 -0.1363 0.033 Uiso 1 calc . . C18 C 0.21677(5) 0.88337(19) -0.02958(10) 0.0297(4) Uani 1 d . . H18 H 0.2271 0.9742 -0.0162 0.036 Uiso 1 calc . . C15 C 0.16032(5) 0.60379(17) 0.06314(9) 0.0229(3) Uani 1 d . . C22 C 0.05202(5) 0.01644(18) 0.20917(10) 0.0298(4) Uani 1 d . . H22A H 0.0401 -0.0272 0.2524 0.036 Uiso 1 calc . . H22B H 0.0807 0.0156 0.2214 0.036 Uiso 1 calc . . C24 C 0.05947(6) -0.2196(2) 0.14827(12) 0.0402(5) Uani 1 d . . H24A H 0.0878 -0.2122 0.1597 0.06 Uiso 1 calc . . H24B H 0.0536 -0.273 0.101 0.06 Uiso 1 calc . . H24C H 0.0482 -0.2685 0.19 0.06 Uiso 1 calc . . C23 C 0.04195(5) -0.07168(19) 0.13903(10) 0.0317(4) Uani 1 d . . H23A H 0.052 -0.0247 0.0946 0.038 Uiso 1 calc . . H23B H 0.0132 -0.0791 0.1292 0.038 Uiso 1 calc . . 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 O2 0.0202(5) 0.0211(6) 0.0214(6) 0.0023(5) 0.0007(4) 0.0017(4) C13 0.0195(7) 0.0206(8) 0.0149(8) 0.0003(6) -0.0022(6) 0.0000(6) C11 0.0269(8) 0.0251(9) 0.0203(8) 0.0036(7) 0.0005(7) -0.0035(7) C12 0.0188(7) 0.0249(8) 0.0144(7) 0.0004(6) -0.0015(6) -0.0006(6) C10 0.0331(9) 0.0198(8) 0.0264(9) -0.0001(7) -0.0007(7) 0.0015(7) C25 0.0271(8) 0.0319(10) 0.0208(9) 0.0065(7) 0.0003(7) 0.0030(7) C9 0.0250(8) 0.0254(9) 0.0211(8) -0.0020(7) 0.0011(7) 0.0045(7) C26 0.0302(9) 0.0294(10) 0.0481(12) 0.0129(9) 0.0034(8) 0.0032(8) C27 0.0345(11) 0.0460(13) 0.0862(18) 0.0363(13) -0.0032(11) 0.0031(10) O6 0.0406(7) 0.0306(7) 0.0185(6) 0.0003(5) 0.0044(5) 0.0032(5) O7 0.0342(7) 0.0494(8) 0.0276(7) -0.0070(6) 0.0087(5) 0.0030(6) C8 0.0199(7) 0.0259(8) 0.0127(7) -0.0017(6) -0.0011(6) -0.0002(6) C29 0.0381(10) 0.0389(11) 0.0330(10) -0.0040(9) 0.0061(8) 0.0055(9) C28 0.0443(12) 0.0316(11) 0.0562(14) -0.0022(10) 0.0048(10) 0.0031(9) C31 0.0408(11) 0.0378(11) 0.0341(11) -0.0054(9) 0.0015(9) -0.0048(9) C30 0.0497(13) 0.0598(15) 0.0510(14) 0.0165(12) 0.0019(11) -0.0032(11) O1 0.0225(6) 0.0285(6) 0.0209(6) 0.0035(5) 0.0056(5) -0.0053(5) O3 0.0555(8) 0.0392(8) 0.0176(6) -0.0041(5) 0.0072(6) -0.0191(6) O5 0.0322(7) 0.0379(7) 0.0207(6) 0.0001(5) 0.0106(5) -0.0070(5) O4 0.0325(6) 0.0296(7) 0.0185(6) -0.0038(5) 0.0078(5) -0.0075(5) N1 0.0240(7) 0.0315(8) 0.0139(6) 0.0006(6) 0.0034(5) -0.0063(6) C16 0.0198(7) 0.0256(9) 0.0195(8) 0.0021(7) 0.0020(6) -0.0011(6) C5 0.0185(7) 0.0237(8) 0.0193(8) -0.0027(7) 0.0030(6) 0.0002(6) C6 0.0225(8) 0.0267(9) 0.0147(8) 0.0001(6) 0.0021(6) 0.0006(7) C7 0.0209(7) 0.0289(9) 0.0156(8) -0.0010(6) 0.0023(6) -0.0028(6) C21 0.0170(7) 0.0240(8) 0.0213(8) 0.0006(7) 0.0013(6) -0.0011(6) C2 0.0174(7) 0.0261(9) 0.0195(8) -0.0005(7) 0.0015(6) -0.0019(6) C4 0.0198(7) 0.0225(8) 0.0188(8) 0.0005(6) 0.0072(6) 0.0002(6) C3 0.0200(7) 0.0219(8) 0.0175(8) -0.0007(6) 0.0027(6) 0.0028(6) C17 0.0286(8) 0.0261(9) 0.0222(9) -0.0021(7) 0.0035(7) -0.0032(7) C14 0.0181(7) 0.0276(9) 0.0183(8) 0.0031(7) 0.0017(6) 0.0007(6) C1 0.0211(7) 0.0237(8) 0.0199(8) -0.0008(7) 0.0062(6) -0.0017(6) C20 0.0195(7) 0.0338(10) 0.0194(8) 0.0016(7) 0.0038(6) 0.0009(7) C19 0.0270(8) 0.0322(10) 0.0249(9) 0.0065(7) 0.0059(7) -0.0049(7) C18 0.0320(9) 0.0279(9) 0.0293(10) -0.0003(8) 0.0028(7) -0.0084(7) C15 0.0245(8) 0.0251(9) 0.0193(8) 0.0003(7) 0.0027(7) 0.0000(7) C22 0.0347(9) 0.0279(9) 0.0262(9) 0.0051(7) 0.0000(7) -0.0074(8) C24 0.0480(12) 0.0291(10) 0.0418(12) 0.0007(9) -0.0043(9) -0.0068(9) C23 0.0347(9) 0.0324(10) 0.0274(9) 0.0021(8) -0.0003(8) -0.0063(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O2 C13 1.3882(18) . ? O2 C25 1.4337(19) . ? C13 C8 1.393(2) . ? C13 C12 1.395(2) . ? C11 C10 1.380(2) . ? C11 C12 1.393(2) . ? C11 H11 0.95 . ? C12 C14 1.520(2) . ? C10 C9 1.386(2) . ? C10 H10 0.95 . ? C25 C26 1.501(2) . ? C25 H25A 0.99 . ? C25 H25B 0.99 . ? C9 C8 1.390(2) . ? C9 H9 0.95 . ? C26 C27 1.513(3) . ? C26 H26A 0.99 . ? C26 H26B 0.99 . ? C27 H27A 0.98 . ? C27 H27B 0.98 . ? C27 H27C 0.98 . ? O6 C29 1.428(2) . ? O6 H6A 0.84 . ? O7 C31 1.423(2) . ? O7 H7 0.84 . ? C8 C7 1.519(2) 2 ? C29 C28 1.505(3) . ? C29 H29A 0.99 . ? C29 H29B 0.99 . ? C28 H28A 0.98 . ? C28 H28B 0.98 . ? C28 H28C 0.98 . ? C31 C30 1.488(3) . ? C31 H31A 0.99 . ? C31 H31B 0.99 . ? C30 H30A 0.98 . ? C30 H30B 0.98 . ? C30 H30C 0.98 . ? O1 C4 1.3830(18) . ? O1 C22 1.442(2) . ? O3 C15 1.2347(19) . ? O5 C20 1.363(2) . ? O5 H5 0.84 . ? O4 C21 1.3634(19) . ? O4 H4 0.84 . ? N1 C15 1.341(2) . ? N1 C1 1.421(2) . ? N1 H1 0.88 . ? C16 C21 1.395(2) . ? C16 C17 1.396(2) . ? C16 C15 1.495(2) . ? C5 C6 1.388(2) . ? C5 C4 1.396(2) . ? C5 C7 1.513(2) . ? C6 C1 1.389(2) . ? C6 H6 0.95 . ? C7 C8 1.519(2) 2 ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C21 C20 1.408(2) . ? C2 C1 1.389(2) . ? C2 C3 1.395(2) . ? C2 H2 0.95 . ? C4 C3 1.396(2) . ? C3 C14 1.517(2) . ? C17 C18 1.378(2) . ? C17 H17 0.95 . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C20 C19 1.378(2) . ? C19 C18 1.385(2) . ? C19 H19 0.95 . ? C18 H18 0.95 . ? C22 C23 1.505(2) . ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? C24 C23 1.524(3) . ? C24 H24A 0.98 . ? C24 H24B 0.98 . ? C24 H24C 0.98 . ? C23 H23A 0.99 . ? C23 H23B 0.99 . ? 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 C13 O2 C25 112.94(12) . . ? O2 C13 C8 118.73(13) . . ? O2 C13 C12 119.51(13) . . ? C8 C13 C12 121.66(14) . . ? C10 C11 C12 120.87(15) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C11 C12 C13 118.38(14) . . ? C11 C12 C14 119.84(14) . . ? C13 C12 C14 121.50(14) . . ? C11 C10 C9 119.62(16) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? O2 C25 C26 108.07(14) . . ? O2 C25 H25A 110.1 . . ? C26 C25 H25A 110.1 . . ? O2 C25 H25B 110.1 . . ? C26 C25 H25B 110.1 . . ? H25A C25 H25B 108.4 . . ? C10 C9 C8 121.23(15) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C25 C26 C27 111.71(17) . . ? C25 C26 H26A 109.3 . . ? C27 C26 H26A 109.3 . . ? C25 C26 H26B 109.3 . . ? C27 C26 H26B 109.3 . . ? H26A C26 H26B 107.9 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 O6 H6A 109.5 . . ? C31 O7 H7 109.5 . . ? C9 C8 C13 118.10(14) . . ? C9 C8 C7 120.19(14) . 2 ? C13 C8 C7 121.60(14) . 2 ? O6 C29 C28 112.44(16) . . ? O6 C29 H29A 109.1 . . ? C28 C29 H29A 109.1 . . ? O6 C29 H29B 109.1 . . ? C28 C29 H29B 109.1 . . ? H29A C29 H29B 107.8 . . ? C29 C28 H28A 109.5 . . ? C29 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C29 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O7 C31 C30 112.43(17) . . ? O7 C31 H31A 109.1 . . ? C30 C31 H31A 109.1 . . ? O7 C31 H31B 109.1 . . ? C30 C31 H31B 109.1 . . ? H31A C31 H31B 107.8 . . ? C31 C30 H30A 109.5 . . ? C31 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C31 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C4 O1 C22 114.40(12) . . ? C20 O5 H5 109.5 . . ? C21 O4 H4 109.5 . . ? C15 N1 C1 127.67(14) . . ? C15 N1 H1 116.2 . . ? C1 N1 H1 116.2 . . ? C21 C16 C17 118.82(15) . . ? C21 C16 C15 124.86(14) . . ? C17 C16 C15 116.32(14) . . ? C6 C5 C4 118.36(14) . . ? C6 C5 C7 121.45(14) . . ? C4 C5 C7 119.84(14) . . ? C5 C6 C1 121.13(14) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? C5 C7 C8 110.13(13) . 2 ? C5 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 2 . ? C5 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 2 . ? H7A C7 H7B 108.1 . . ? O4 C21 C16 120.86(14) . . ? O4 C21 C20 119.37(14) . . ? C16 C21 C20 119.77(15) . . ? C1 C2 C3 119.93(14) . . ? C1 C2 H2 120 . . ? C3 C2 H2 120 . . ? O1 C4 C3 120.07(14) . . ? O1 C4 C5 118.52(13) . . ? C3 C4 C5 121.11(14) . . ? C2 C3 C4 119.20(14) . . ? C2 C3 C14 120.10(14) . . ? C4 C3 C14 120.24(14) . . ? C18 C17 C16 120.90(16) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C3 C14 C12 109.09(12) . . ? C3 C14 H14A 109.9 . . ? C12 C14 H14A 109.9 . . ? C3 C14 H14B 109.9 . . ? C12 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? C6 C1 C2 119.90(14) . . ? C6 C1 N1 116.91(14) . . ? C2 C1 N1 123.18(14) . . ? O5 C20 C19 124.55(15) . . ? O5 C20 C21 115.17(15) . . ? C19 C20 C21 120.28(15) . . ? C20 C19 C18 119.85(16) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C17 C18 C19 120.35(16) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? O3 C15 N1 122.71(15) . . ? O3 C15 C16 120.12(15) . . ? N1 C15 C16 117.14(14) . . ? O1 C22 C23 113.41(14) . . ? O1 C22 H22A 108.9 . . ? C23 C22 H22A 108.9 . . ? O1 C22 H22B 108.9 . . ? C23 C22 H22B 108.9 . . ? H22A C22 H22B 107.7 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C23 C24 111.14(15) . . ? C22 C23 H23A 109.4 . . ? C24 C23 H23A 109.4 . . ? C22 C23 H23B 109.4 . . ? C24 C23 H23B 109.4 . . ? H23A C23 H23B 108 . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 939476' ####################################################################### # # 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_1PrOH _audit_creation_date 2013-05-15T22:15:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C54 H58 N2 O10, 4(C3 H8 O)' _chemical_formula_sum 'C66 H90 N2 O14' _chemical_formula_weight 1135.40 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'C 2/c' _space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 36.8591(18) _cell_length_b 9.2839(5) _cell_length_c 18.0544(9) _cell_angle_alpha 90 _cell_angle_beta 90.6340(10) _cell_angle_gamma 90 _cell_volume 6177.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5318 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 28.96 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2448 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe X-ray _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bluker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_unetI/netI 0.036 _diffrn_reflns_number 17560 _diffrn_reflns_limit_h_min -49 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 28.96 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.915 _reflns_number_total 7502 _reflns_number_gt 5563 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'SHELXS-2013 (Sheldrick, 2013)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0486P)^2^+7.1624P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7502 _refine_ls_number_parameters 409 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1283 _refine_ls_wR_factor_gt 0.1152 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.8 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O4 O -0.20781(3) 0.24378(14) 0.33264(6) 0.0279(3) Uani 1 1 d . . . H4 H -0.2284 0.2563 0.3134 0.042 Uiso 1 1 calc R . . C1 C -0.12171(4) 0.47695(17) 0.36153(9) 0.0214(3) Uani 1 1 d . . . C2 C -0.12236(4) 0.51764(17) 0.28702(9) 0.0215(3) Uani 1 1 d . . . H2 H -0.1409 0.4816 0.2552 0.026 Uiso 1 1 calc R . . C3 C -0.09632(4) 0.60983(17) 0.25877(9) 0.0215(3) Uani 1 1 d . . . C4 C -0.06982(4) 0.66477(17) 0.30720(9) 0.0216(3) Uani 1 1 d . A . C5 C -0.06766(4) 0.61922(17) 0.38078(9) 0.0212(3) Uani 1 1 d . . . C6 C -0.09404(4) 0.52619(17) 0.40802(9) 0.0219(3) Uani 1 1 d . . . H6 H -0.0931 0.4964 0.4584 0.026 Uiso 1 1 calc R . . C7 C -0.03451(4) 0.65605(18) 0.42730(9) 0.0225(3) Uani 1 1 d . . . H7A H -0.039 0.6319 0.4798 0.027 Uiso 1 1 calc R . . H7B H -0.0295 0.7606 0.424 0.027 Uiso 1 1 calc R . . C8 C -0.00193(4) 0.57178(17) 0.39980(8) 0.0199(3) Uani 1 1 d . . . C9 C -0.00498(4) 0.42400(17) 0.38763(9) 0.0231(3) Uani 1 1 d . . . H9 H -0.0272 0.3767 0.3984 0.028 Uiso 1 1 calc R . . C10 C 0.02369(5) 0.34492(17) 0.36012(9) 0.0250(3) Uani 1 1 d . . . H10 H 0.0214 0.2438 0.3536 0.03 Uiso 1 1 calc R . . C11 C 0.05569(4) 0.41384(18) 0.34212(9) 0.0238(3) Uani 1 1 d . . . H11 H 0.0752 0.3595 0.3225 0.029 Uiso 1 1 calc R . . C12 C 0.05973(4) 0.56177(17) 0.35230(8) 0.0203(3) Uani 1 1 d . . . C13 C 0.03089(4) 0.63860(16) 0.38260(8) 0.0194(3) Uani 1 1 d . . . C14 C 0.09354(4) 0.63643(18) 0.32375(9) 0.0226(3) Uani 1 1 d . . . H14A H 0.0921 0.7412 0.3336 0.027 Uiso 1 1 calc R . . H14B H 0.1153 0.5981 0.3495 0.027 Uiso 1 1 calc R . . C15 C -0.15651(4) 0.33011(17) 0.45215(9) 0.0223(3) Uani 1 1 d . . . C16 C -0.18712(4) 0.22512(17) 0.45913(9) 0.0212(3) Uani 1 1 d . . . C17 C -0.19211(4) 0.16583(18) 0.52978(9) 0.0244(3) Uani 1 1 d . . . H17 H -0.1757 0.19 0.5688 0.029 Uiso 1 1 calc R . . C18 C -0.22042(5) 0.07320(19) 0.54334(10) 0.0273(4) Uani 1 1 d . . . H18 H -0.2238 0.0362 0.5918 0.033 Uiso 1 1 calc R . . C19 C -0.24404(4) 0.03348(18) 0.48636(10) 0.0254(4) Uani 1 1 d . . . H19 H -0.2634 -0.0316 0.4957 0.03 Uiso 1 1 calc R . . C20 C -0.23935(4) 0.08899(17) 0.41597(9) 0.0228(3) Uani 1 1 d . . . C21 C -0.21150(4) 0.18737(17) 0.40204(9) 0.0216(3) Uani 1 1 d . . . C25 C 0.04564(5) 0.82348(19) 0.46622(10) 0.0304(4) Uani 1 1 d . . . H25A H 0.0686 0.7736 0.4792 0.036 Uiso 1 1 calc R . . H25B H 0.0269 0.7937 0.5019 0.036 Uiso 1 1 calc R . . C26 C 0.05100(6) 0.9850(2) 0.46942(12) 0.0411(5) Uani 1 1 d . . . H26A H 0.029 1.0328 0.4495 0.049 Uiso 1 1 calc R . . H26B H 0.0539 1.0146 0.5218 0.049 Uiso 1 1 calc R . . C27 C 0.08327(6) 1.0363(2) 0.42680(19) 0.0690(9) Uani 1 1 d . . . H27A H 0.1051 0.986 0.4445 0.104 Uiso 1 1 calc R . . H27B H 0.0863 1.1402 0.4341 0.104 Uiso 1 1 calc R . . H27C H 0.0795 1.0162 0.374 0.104 Uiso 1 1 calc R . . N1 N -0.14926(4) 0.37977(15) 0.38379(8) 0.0232(3) Uani 1 1 d . . . H1 H -0.1635 0.3476 0.3481 0.028 Uiso 1 1 calc R . . O1 O -0.04346(3) 0.75454(13) 0.27934(7) 0.0291(3) Uani 1 1 d . . . O2 O 0.03451(3) 0.78638(12) 0.39247(6) 0.0219(2) Uani 1 1 d . . . O3 O -0.13910(3) 0.36827(14) 0.50765(6) 0.0285(3) Uani 1 1 d . . . O5 O -0.26097(3) 0.05257(13) 0.35630(6) 0.0274(3) Uani 1 1 d . . . H5 H -0.2807 0.0186 0.3714 0.041 Uiso 1 1 calc R . . C28 C 0.15827(5) 0.3191(2) 0.40861(10) 0.0316(4) Uani 1 1 d . . . H28 H 0.1313 0.3294 0.4067 0.038 Uiso 1 1 calc R . . C29 C 0.16889(6) 0.2654(2) 0.48416(11) 0.0392(5) Uani 1 1 d . . . H29A H 0.1952 0.2513 0.4866 0.059 Uiso 1 1 calc R . . H29B H 0.1567 0.1736 0.4937 0.059 Uiso 1 1 calc R . . H29C H 0.1617 0.3362 0.5215 0.059 Uiso 1 1 calc R . . C30 C 0.16933(6) 0.2192(2) 0.34733(11) 0.0412(5) Uani 1 1 d . . . H30A H 0.1597 0.2551 0.3 0.062 Uiso 1 1 calc R . . H30B H 0.1597 0.1227 0.3568 0.062 Uiso 1 1 calc R . . H30C H 0.1959 0.2148 0.3452 0.062 Uiso 1 1 calc R . . O7 O 0.17406(3) 0.45801(13) 0.39416(7) 0.0283(3) Uani 1 1 d . . . H7 H 0.1648 0.5197 0.4223 0.042 Uiso 1 1 calc R . . C31 C 0.21744(6) 0.6728(2) 0.16646(12) 0.0398(5) Uani 1 1 d . . . H31A H 0.2269 0.7314 0.1259 0.06 Uiso 1 1 calc R . . H31B H 0.1972 0.6138 0.148 0.06 Uiso 1 1 calc R . . H31C H 0.2367 0.61 0.1858 0.06 Uiso 1 1 calc R . . C32 C 0.20432(5) 0.7699(2) 0.22731(10) 0.0304(4) Uani 1 1 d . . . H32 H 0.1942 0.7078 0.2673 0.036 Uiso 1 1 calc R . . C33 C 0.17457(5) 0.8706(2) 0.20127(14) 0.0463(5) Uani 1 1 d . . . H33A H 0.1677 0.9343 0.242 0.069 Uiso 1 1 calc R . . H33B H 0.1534 0.8142 0.1851 0.069 Uiso 1 1 calc R . . H33C H 0.1833 0.9286 0.1598 0.069 Uiso 1 1 calc R . . O6 O 0.23437(3) 0.84998(15) 0.25835(7) 0.0345(3) Uani 1 1 d . . . H6A H 0.2422 0.9081 0.2266 0.052 Uiso 1 1 calc R . . C22A C -0.04081(18) 0.8965(5) 0.2949(4) 0.0375(15) Uani 0.427(8) 1 d P A 1 H22A H -0.0291 0.9471 0.2532 0.045 Uiso 0.427(8) 1 calc PR A 1 H22B H -0.0255 0.9103 0.3397 0.045 Uiso 0.427(8) 1 calc PR A 1 C23A C -0.07639(19) 0.9570(7) 0.3072(3) 0.0449(16) Uani 0.427(8) 1 d P A 1 H23A H -0.0873 0.9103 0.351 0.054 Uiso 0.427(8) 1 calc PR A 1 H23B H -0.0922 0.9366 0.2638 0.054 Uiso 0.427(8) 1 calc PR A 1 C24A C -0.0747(3) 1.1309(13) 0.3208(7) 0.038(3) Uani 0.427(8) 1 d P A 1 H24A H -0.0607 1.1511 0.3661 0.057 Uiso 0.427(8) 1 calc PR A 1 H24B H -0.0993 1.1687 0.3257 0.057 Uiso 0.427(8) 1 calc PR A 1 H24C H -0.0629 1.177 0.2786 0.057 Uiso 0.427(8) 1 calc PR A 1 C22B C -0.05733(13) 0.9050(4) 0.2651(3) 0.0336(11) Uani 0.573(8) 1 d P A 2 H22C H -0.0407 0.9548 0.2309 0.04 Uiso 0.573(8) 1 calc PR A 2 H22D H -0.0814 0.8993 0.2406 0.04 Uiso 0.573(8) 1 calc PR A 2 C23B C -0.06046(13) 0.9912(4) 0.3342(2) 0.0354(11) Uani 0.573(8) 1 d P A 2 H23C H -0.0367 0.9949 0.3603 0.042 Uiso 0.573(8) 1 calc PR A 2 H23D H -0.0783 0.9462 0.3676 0.042 Uiso 0.573(8) 1 calc PR A 2 C24B C -0.0727(3) 1.1437(11) 0.3135(7) 0.075(4) Uani 0.573(8) 1 d P A 2 H24D H -0.053 1.1936 0.2881 0.112 Uiso 0.573(8) 1 calc PR A 2 H24E H -0.079 1.1966 0.3585 0.112 Uiso 0.573(8) 1 calc PR A 2 H24F H -0.094 1.1383 0.2806 0.112 Uiso 0.573(8) 1 calc PR A 2 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 O4 0.0235(6) 0.0377(7) 0.0226(6) 0.0045(5) -0.0008(5) -0.0087(5) C1 0.0173(7) 0.0204(8) 0.0264(8) -0.0015(6) 0.0030(6) 0.0000(6) C2 0.0165(7) 0.0227(8) 0.0253(8) -0.0030(6) -0.0011(6) 0.0003(6) C3 0.0193(7) 0.0208(8) 0.0244(8) -0.0015(6) 0.0015(6) 0.0032(6) C4 0.0182(7) 0.0206(8) 0.0260(8) -0.0029(6) 0.0031(6) -0.0011(6) C5 0.0187(7) 0.0199(7) 0.0251(8) -0.0052(6) 0.0014(6) 0.0010(6) C6 0.0192(7) 0.0241(8) 0.0225(8) -0.0006(6) 0.0009(6) 0.0008(6) C7 0.0201(8) 0.0235(8) 0.0238(8) -0.0041(6) 0.0013(6) -0.0028(6) C8 0.0207(7) 0.0223(8) 0.0167(7) -0.0003(6) -0.0013(6) -0.0008(6) C9 0.0236(8) 0.0225(8) 0.0232(8) 0.0019(6) -0.0012(6) -0.0047(6) C10 0.0318(9) 0.0159(7) 0.0272(9) 0.0001(6) -0.0022(7) -0.0008(7) C11 0.0248(8) 0.0233(8) 0.0232(8) -0.0015(6) -0.0019(6) 0.0037(7) C12 0.0200(7) 0.0231(8) 0.0178(7) 0.0005(6) -0.0025(6) 0.0007(6) C13 0.0228(8) 0.0179(7) 0.0176(7) -0.0007(6) -0.0019(6) -0.0007(6) C14 0.0181(7) 0.0241(8) 0.0257(8) -0.0023(7) -0.0003(6) 0.0004(6) C15 0.0183(7) 0.0232(8) 0.0253(8) -0.0004(6) 0.0002(6) 0.0028(6) C16 0.0189(7) 0.0206(7) 0.0244(8) 0.0001(6) 0.0029(6) 0.0018(6) C17 0.0240(8) 0.0245(8) 0.0245(8) 0.0009(7) -0.0007(6) 0.0020(7) C18 0.0266(8) 0.0286(9) 0.0268(9) 0.0061(7) 0.0030(7) 0.0012(7) C19 0.0210(8) 0.0228(8) 0.0325(9) 0.0038(7) 0.0035(7) -0.0019(7) C20 0.0184(7) 0.0223(8) 0.0277(9) -0.0014(7) 0.0012(6) 0.0006(6) C21 0.0204(7) 0.0224(8) 0.0220(8) 0.0012(6) 0.0035(6) 0.0009(6) C25 0.0371(10) 0.0232(8) 0.0306(9) -0.0053(7) -0.0066(7) -0.0038(7) C26 0.0491(12) 0.0233(9) 0.0507(13) -0.0104(9) -0.0102(10) -0.0032(8) C27 0.0398(13) 0.0298(11) 0.137(3) 0.0013(14) -0.0013(15) -0.0132(10) N1 0.0197(6) 0.0267(7) 0.0233(7) 0.0002(6) -0.0006(5) -0.0053(6) O1 0.0275(6) 0.0306(6) 0.0293(6) 0.0026(5) -0.0001(5) -0.0114(5) O2 0.0235(6) 0.0178(5) 0.0244(6) -0.0018(4) -0.0004(4) -0.0026(4) O3 0.0256(6) 0.0362(7) 0.0237(6) -0.0016(5) -0.0022(5) -0.0072(5) O5 0.0217(6) 0.0324(7) 0.0281(6) 0.0000(5) 0.0001(5) -0.0083(5) C28 0.0289(9) 0.0307(9) 0.0352(10) 0.0009(8) -0.0010(7) -0.0067(7) C29 0.0531(12) 0.0313(10) 0.0329(10) 0.0017(8) -0.0017(9) 0.0006(9) C30 0.0579(13) 0.0338(10) 0.0320(10) -0.0013(8) -0.0019(9) 0.0027(9) O7 0.0242(6) 0.0275(6) 0.0332(7) -0.0006(5) 0.0027(5) -0.0045(5) C31 0.0391(11) 0.0396(11) 0.0407(11) -0.0030(9) -0.0044(9) -0.0037(9) C32 0.0264(9) 0.0305(9) 0.0342(10) 0.0045(8) -0.0024(7) -0.0063(7) C33 0.0301(10) 0.0372(11) 0.0714(16) 0.0069(11) -0.0044(10) -0.0014(9) O6 0.0354(7) 0.0381(7) 0.0297(7) 0.0036(6) -0.0054(5) -0.0101(6) C22A 0.040(3) 0.033(3) 0.039(3) 0.005(2) -0.003(3) -0.008(2) C23A 0.048(4) 0.054(3) 0.033(3) -0.004(3) -0.002(3) -0.022(3) C24A 0.038(4) 0.034(5) 0.041(5) 0.017(3) -0.002(3) -0.015(4) C22B 0.038(2) 0.0223(16) 0.041(2) 0.0040(15) -0.0049(19) -0.0024(15) C23B 0.043(2) 0.0264(18) 0.037(2) -0.0025(15) -0.0022(18) -0.0020(16) C24B 0.127(8) 0.036(4) 0.060(6) -0.021(4) -0.032(5) 0.031(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O4 C21 1.3663(19) . ? O4 H4 0.84 . ? C1 C6 1.391(2) . ? C1 C2 1.397(2) . ? C1 N1 1.420(2) . ? C2 C3 1.387(2) . ? C2 H2 0.95 . ? C3 C4 1.400(2) . ? C3 C14 1.515(2) 2 ? C4 O1 1.3793(19) . ? C4 C5 1.396(2) . ? C5 C6 1.394(2) . ? C5 C7 1.514(2) . ? C6 H6 0.95 . ? C7 C8 1.521(2) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 C9 1.394(2) . ? C8 C13 1.397(2) . ? C9 C10 1.384(2) . ? C9 H9 0.95 . ? C10 C11 1.384(2) . ? C10 H10 0.95 . ? C11 C12 1.393(2) . ? C11 H11 0.95 . ? C12 C13 1.397(2) . ? C12 C14 1.521(2) . ? C13 O2 1.3898(18) . ? C14 C3 1.515(2) 2 ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 O3 1.236(2) . ? C15 N1 1.347(2) . ? C15 C16 1.498(2) . ? C16 C17 1.403(2) . ? C16 C21 1.404(2) . ? C17 C18 1.376(2) . ? C17 H17 0.95 . ? C18 C19 1.390(2) . ? C18 H18 0.95 . ? C19 C20 1.384(2) . ? C19 H19 0.95 . ? C20 O5 1.375(2) . ? C20 C21 1.399(2) . ? C25 O2 1.431(2) . ? C25 C26 1.514(2) . ? C25 H25A 0.99 . ? C25 H25B 0.99 . ? C26 C27 1.501(3) . ? C26 H26A 0.99 . ? C26 H26B 0.99 . ? C27 H27A 0.98 . ? C27 H27B 0.98 . ? C27 H27C 0.98 . ? N1 H1 0.88 . ? O1 C22A 1.351(5) . ? O1 C22B 1.509(4) . ? O5 H5 0.84 . ? C28 O7 1.440(2) . ? C28 C29 1.500(3) . ? C28 C30 1.503(3) . ? C28 H28 1 . ? C29 H29A 0.98 . ? C29 H29B 0.98 . ? C29 H29C 0.98 . ? C30 H30A 0.98 . ? C30 H30B 0.98 . ? C30 H30C 0.98 . ? O7 H7 0.84 . ? C31 C32 1.505(3) . ? C31 H31A 0.98 . ? C31 H31B 0.98 . ? C31 H31C 0.98 . ? C32 O6 1.442(2) . ? C32 C33 1.512(3) . ? C32 H32 1 . ? C33 H33A 0.98 . ? C33 H33B 0.98 . ? C33 H33C 0.98 . ? O6 H6A 0.84 . ? C22A C23A 1.446(10) . ? C22A H22A 0.99 . ? C22A H22B 0.99 . ? C23A C24A 1.633(14) . ? C23A H23A 0.99 . ? C23A H23B 0.99 . ? C24A H24A 0.98 . ? C24A H24B 0.98 . ? C24A H24C 0.98 . ? C22B C23B 1.487(7) . ? C22B H22C 0.99 . ? C22B H22D 0.99 . ? C23B C24B 1.531(11) . ? C23B H23C 0.99 . ? C23B H23D 0.99 . ? C24B H24D 0.98 . ? C24B H24E 0.98 . ? C24B H24F 0.98 . ? 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 C21 O4 H4 109.5 . . ? C6 C1 C2 119.79(14) . . ? C6 C1 N1 124.04(15) . . ? C2 C1 N1 116.09(14) . . ? C3 C2 C1 121.08(15) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 118.42(15) . . ? C2 C3 C14 121.12(14) . 2 ? C4 C3 C14 120.03(14) . 2 ? O1 C4 C5 119.81(14) . . ? O1 C4 C3 118.81(14) . . ? C5 C4 C3 121.08(14) . . ? C6 C5 C4 119.40(15) . . ? C6 C5 C7 120.38(15) . . ? C4 C5 C7 119.79(14) . . ? C1 C6 C5 120.01(15) . . ? C1 C6 H6 120 . . ? C5 C6 H6 120 . . ? C5 C7 C8 109.75(13) . . ? C5 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? C5 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C9 C8 C13 118.07(14) . . ? C9 C8 C7 119.66(14) . . ? C13 C8 C7 122.19(14) . . ? C10 C9 C8 121.20(15) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 119.71(15) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C12 120.99(15) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C11 C12 C13 118.32(14) . . ? C11 C12 C14 119.42(14) . . ? C13 C12 C14 122.01(14) . . ? O2 C13 C12 118.82(14) . . ? O2 C13 C8 119.46(13) . . ? C12 C13 C8 121.65(14) . . ? C3 C14 C12 108.89(13) 2 . ? C3 C14 H14A 109.9 2 . ? C12 C14 H14A 109.9 . . ? C3 C14 H14B 109.9 2 . ? C12 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? O3 C15 N1 122.58(15) . . ? O3 C15 C16 120.21(15) . . ? N1 C15 C16 117.21(14) . . ? C17 C16 C21 118.69(15) . . ? C17 C16 C15 116.00(14) . . ? C21 C16 C15 125.26(14) . . ? C18 C17 C16 120.93(16) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 120.28(16) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C20 C19 C18 119.80(15) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? O5 C20 C19 123.40(14) . . ? O5 C20 C21 116.08(14) . . ? C19 C20 C21 120.51(15) . . ? O4 C21 C20 119.74(14) . . ? O4 C21 C16 120.53(14) . . ? C20 C21 C16 119.72(15) . . ? O2 C25 C26 108.05(15) . . ? O2 C25 H25A 110.1 . . ? C26 C25 H25A 110.1 . . ? O2 C25 H25B 110.1 . . ? C26 C25 H25B 110.1 . . ? H25A C25 H25B 108.4 . . ? C27 C26 C25 113.48(18) . . ? C27 C26 H26A 108.9 . . ? C25 C26 H26A 108.9 . . ? C27 C26 H26B 108.9 . . ? C25 C26 H26B 108.9 . . ? H26A C26 H26B 107.7 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C15 N1 C1 128.81(14) . . ? C15 N1 H1 115.6 . . ? C1 N1 H1 115.6 . . ? C22A O1 C4 124.3(3) . . ? C22A O1 C22B 32.4(3) . . ? C4 O1 C22B 112.51(19) . . ? C13 O2 C25 112.52(12) . . ? C20 O5 H5 109.5 . . ? O7 C28 C29 111.13(15) . . ? O7 C28 C30 107.79(15) . . ? C29 C28 C30 113.20(17) . . ? O7 C28 H28 108.2 . . ? C29 C28 H28 108.2 . . ? C30 C28 H28 108.2 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C28 O7 H7 109.5 . . ? C32 C31 H31A 109.5 . . ? C32 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C32 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O6 C32 C31 109.93(15) . . ? O6 C32 C33 110.70(15) . . ? C31 C32 C33 112.41(17) . . ? O6 C32 H32 107.9 . . ? C31 C32 H32 107.9 . . ? C33 C32 H32 107.9 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 O6 H6A 109.5 . . ? O1 C22A C23A 110.3(6) . . ? O1 C22A H22A 109.6 . . ? C23A C22A H22A 109.6 . . ? O1 C22A H22B 109.6 . . ? C23A C22A H22B 109.6 . . ? H22A C22A H22B 108.1 . . ? C22A C23A C24A 111.9(6) . . ? C22A C23A H23A 109.2 . . ? C24A C23A H23A 109.2 . . ? C22A C23A H23B 109.2 . . ? C24A C23A H23B 109.2 . . ? H23A C23A H23B 107.9 . . ? C23B C22B O1 112.6(4) . . ? C23B C22B H22C 109.1 . . ? O1 C22B H22C 109.1 . . ? C23B C22B H22D 109.1 . . ? O1 C22B H22D 109.1 . . ? H22C C22B H22D 107.8 . . ? C22B C23B C24B 108.5(6) . . ? C22B C23B H23C 110 . . ? C24B C23B H23C 110 . . ? C22B C23B H23D 110 . . ? C24B C23B H23D 110 . . ? H23C C23B H23D 108.4 . . ? C23B C24B H24D 109.5 . . ? C23B C24B H24E 109.5 . . ? H24D C24B H24E 109.5 . . ? C23B C24B H24F 109.5 . . ? H24D C24B H24F 109.5 . . ? H24E C24B H24F 109.5 . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 939477' ####################################################################### # # 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_1BuOH2 _audit_creation_date 2013-08-16T15:39:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C54 H58 N2 O10, 2(C4 H10 O2)' _chemical_formula_sum 'C62 H78 N2 O14' _chemical_formula_weight 1075.26 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'C 2/c' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 36.162(12) _cell_length_b 9.347(3) _cell_length_c 17.877(6) _cell_angle_alpha 90 _cell_angle_beta 112.125(4) _cell_angle_gamma 90 _cell_volume 5597(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 1558 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 17.86 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.005 _exptl_crystal_density_diffrn 1.276 _exptl_crystal_F_000 2304 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.09 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe X-ray _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bluker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_number 5842 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.262 _diffrn_reflns_theta_max 17.863 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.381 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 1881 _reflns_number_gt 1507 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'SHELXS-2013 (Sheldrick, 2013)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. EADP restraint was applied to the disordered atoms. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+12.6348P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1881 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.059 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1173 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.211 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.035 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.61638(16) 0.1106(5) 1.0112(3) 0.0259(12) Uani 1 d . . C2 C 0.62430(14) 0.1567(5) 0.9453(3) 0.0295(13) Uani 1 d . . H2 H 0.6485 0.1292 0.9399 0.035 Uiso 1 calc . . C3 C 0.59737(16) 0.2424(5) 0.8874(3) 0.0253(12) Uani 1 d . . C4 C 0.56307(16) 0.2841(5) 0.8980(3) 0.0273(12) Uani 1 d . . C5 C 0.55297(14) 0.2328(5) 0.9606(3) 0.0268(12) Uani 1 d . . C6 C 0.58029(18) 0.1456(5) 1.0174(3) 0.0286(12) Uani 1 d . . H6A H 0.5743 0.1092 1.0611 0.034 Uiso 1 calc . . C7 C 0.51187(14) 0.2565(5) 0.9625(3) 0.0317(13) Uani 1 d . . H7A H 0.5061 0.3602 0.9602 0.038 Uiso 1 calc . . H7B H 0.511 0.2181 1.0134 0.038 Uiso 1 calc . . C8 C 0.48064(14) 0.1818(6) 0.8910(3) 0.0253(12) Uani 1 d . . C9 C 0.48375(14) 0.0378(7) 0.8800(3) 0.0346(13) Uani 1 d . . H9 H 0.5041 -0.0151 0.9201 0.042 Uiso 1 calc . . C10 C 0.45829(18) -0.0326(6) 0.8126(4) 0.0435(14) Uani 1 d . . H10 H 0.4601 -0.1333 0.8076 0.052 Uiso 1 calc . . C11 C 0.43028(16) 0.0453(7) 0.7527(3) 0.0378(13) Uani 1 d . . H11 H 0.4135 -0.0021 0.705 0.045 Uiso 1 calc . . C12 C 0.57416(13) 0.1902(6) 0.7400(3) 0.0274(13) Uani 1 d . . C13 C 0.45029(15) 0.2562(6) 0.8319(3) 0.0250(12) Uani 1 d . . C14 C 0.60305(13) 0.2758(5) 0.8099(3) 0.0327(13) Uani 1 d . . H14A H 0.6308 0.2529 0.8163 0.039 Uiso 1 calc . . H14B H 0.5987 0.3793 0.7981 0.039 Uiso 1 calc . . C15 C 0.67652(19) -0.0395(5) 1.0795(3) 0.0330(14) Uani 1 d . . C16 C 0.69910(15) -0.1209(5) 1.1552(3) 0.0294(13) Uani 1 d . . C17 C 0.73111(18) -0.2042(6) 1.1553(3) 0.0465(15) Uani 1 d . . H17 H 0.7374 -0.2074 1.1083 0.056 Uiso 1 calc . . C18 C 0.75393(17) -0.2823(6) 1.2226(4) 0.0605(17) Uani 1 d . . H18 H 0.7754 -0.3392 1.2212 0.073 Uiso 1 calc . . C19 C 0.74569(17) -0.2778(6) 1.2915(4) 0.0488(15) Uani 1 d . . H19 H 0.7614 -0.3315 1.3377 0.059 Uiso 1 calc . . C20 C 0.71468(17) -0.1957(6) 1.2936(3) 0.0362(14) Uani 1 d . . C21 C 0.69168(15) -0.1164(5) 1.2260(4) 0.0288(13) Uani 1 d . . C28 C 0.65098(17) 0.7618(6) 0.8477(3) 0.0658(17) Uani 1 d . . H28A H 0.6357 0.7566 0.7887 0.079 Uiso 1 calc . . H28B H 0.6316 0.7751 0.8741 0.079 Uiso 1 calc . . C29 C 0.67221(16) 0.6220(6) 0.8753(3) 0.0629(17) Uani 1 d . . H29A H 0.6522 0.5442 0.8605 0.075 Uiso 1 calc . . H29B H 0.6902 0.6052 0.8459 0.075 Uiso 1 calc . . C30 C 0.69595(16) 0.6140(6) 0.9630(3) 0.0568(16) Uani 1 d . . H30A H 0.6792 0.6492 0.9921 0.068 Uiso 1 calc . . H30B H 0.719 0.6798 0.9758 0.068 Uiso 1 calc . . C31 C 0.71165(16) 0.4667(6) 0.9956(3) 0.0514(15) Uani 1 d . . H31A H 0.728 0.4742 1.054 0.062 Uiso 1 calc . . H31B H 0.6888 0.4026 0.9891 0.062 Uiso 1 calc . . N1 N 0.64262(14) 0.0257(4) 1.0742(2) 0.0333(11) Uani 1 d . . H1 H 0.6357 0.0138 1.116 0.04 Uiso 1 calc . . O1 O 0.53570(9) 0.3706(3) 0.83907(18) 0.0377(8) Uani 1 d . . O2 O 0.44520(9) 0.4010(4) 0.84104(17) 0.0427(8) Uani 1 d . . O3 O 0.69032(9) -0.0341(3) 1.0246(2) 0.0422(10) Uani 1 d . . O4 O 0.66128(10) -0.0337(4) 1.22966(17) 0.0399(9) Uani 1 d . . H4 H 0.6661 -0.0112 1.2779 0.06 Uiso 1 calc . . O5 O 0.70511(9) -0.1819(3) 1.3601(2) 0.0454(10) Uani 1 d . . H5 H 0.7152 -0.2498 1.3921 0.068 Uiso 1 calc . . O6 O 0.67593(11) 0.8817(4) 0.86383(18) 0.0525(10) Uani 1 d . . H6 H 0.6802 0.9115 0.9107 0.079 Uiso 1 calc . . O7 O 0.73510(10) 0.4059(4) 0.9554(2) 0.0576(10) Uani 1 d . . H7 H 0.7564 0.4524 0.9671 0.086 Uiso 1 calc . . C22A C 0.5297(3) 0.5155(8) 0.8623(5) 0.0377(8) Uani 0.664(5) d A 1 H22A H 0.5277 0.5134 0.916 0.045 Uiso 0.664(5) calc A 1 H22B H 0.5042 0.5535 0.823 0.045 Uiso 0.664(5) calc A 1 C23A C 0.5635(2) 0.6133(8) 0.8651(4) 0.0377(8) Uani 0.664(5) d A 1 H23A H 0.589 0.5778 0.9055 0.045 Uiso 0.664(5) calc A 1 H23B H 0.5659 0.6153 0.8117 0.045 Uiso 0.664(5) calc A 1 C24A C 0.5550(2) 0.7607(8) 0.8876(5) 0.0377(8) Uani 0.664(5) d A 1 H24A H 0.5331 0.8031 0.8421 0.057 Uiso 0.664(5) calc A 1 H24B H 0.5789 0.8202 0.9006 0.057 Uiso 0.664(5) calc A 1 H24C H 0.5475 0.7551 0.9347 0.057 Uiso 0.664(5) calc A 1 C22B C 0.5505(5) 0.5157(17) 0.8426(9) 0.0377(8) Uani 0.336(5) d A 2 H22C H 0.5371 0.5631 0.7897 0.045 Uiso 0.336(5) calc A 2 H22D H 0.5796 0.5137 0.8545 0.045 Uiso 0.336(5) calc A 2 C23B C 0.5429(4) 0.5958(16) 0.9052(9) 0.0377(8) Uani 0.336(5) d A 2 H23C H 0.5512 0.5362 0.9546 0.045 Uiso 0.336(5) calc A 2 H23D H 0.5137 0.6111 0.8874 0.045 Uiso 0.336(5) calc A 2 C24B C 0.5649(5) 0.7500(17) 0.9288(9) 0.0377(8) Uani 0.336(5) d A 2 H24D H 0.5895 0.7491 0.9178 0.057 Uiso 0.336(5) calc A 2 H24E H 0.5714 0.769 0.9862 0.057 Uiso 0.336(5) calc A 2 H24F H 0.5471 0.825 0.8965 0.057 Uiso 0.336(5) calc A 2 C25A C 0.4062(4) 0.3989(14) 0.8626(8) 0.0427(8) Uani 0.451(5) d B 3 H25A H 0.3853 0.3368 0.8248 0.051 Uiso 0.451(5) calc B 3 H25B H 0.4125 0.3646 0.9185 0.051 Uiso 0.451(5) calc B 3 C26A C 0.3930(3) 0.5528(13) 0.8538(6) 0.0427(8) Uani 0.451(5) d B 3 H26A H 0.3885 0.5852 0.7983 0.051 Uiso 0.451(5) calc B 3 H26B H 0.4147 0.612 0.8917 0.051 Uiso 0.451(5) calc B 3 C27A C 0.3551(3) 0.5767(14) 0.8702(7) 0.0427(8) Uani 0.451(5) d B 3 H27A H 0.335 0.5056 0.8405 0.064 Uiso 0.451(5) calc B 3 H27B H 0.3447 0.673 0.8524 0.064 Uiso 0.451(5) calc B 3 H27C H 0.3611 0.567 0.9282 0.064 Uiso 0.451(5) calc B 3 C25B C 0.4256(3) 0.4533(11) 0.8877(6) 0.0427(8) Uani 0.549(5) d B 4 H25C H 0.4321 0.5558 0.8992 0.051 Uiso 0.549(5) calc B 4 H25D H 0.4346 0.4013 0.9398 0.051 Uiso 0.549(5) calc B 4 C26B C 0.3823(3) 0.4367(12) 0.8466(5) 0.0427(8) Uani 0.549(5) d B 4 H26C H 0.3761 0.3354 0.8307 0.051 Uiso 0.549(5) calc B 4 H26D H 0.3731 0.4952 0.7967 0.051 Uiso 0.549(5) calc B 4 C27B C 0.3599(3) 0.4828(11) 0.9006(6) 0.0427(8) Uani 0.549(5) d B 4 H27D H 0.3664 0.417 0.9465 0.064 Uiso 0.549(5) calc B 4 H27E H 0.3311 0.4806 0.8692 0.064 Uiso 0.549(5) calc B 4 H27F H 0.3679 0.5801 0.9205 0.064 Uiso 0.549(5) calc B 4 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 C1 0.023(4) 0.030(3) 0.015(4) 0.010(3) -0.004(3) 0.003(3) C2 0.030(4) 0.035(3) 0.020(3) 0.006(3) 0.005(3) -0.004(3) C3 0.024(4) 0.033(3) 0.017(4) 0.001(3) 0.006(3) -0.007(3) C4 0.034(4) 0.026(3) 0.014(4) 0.004(3) 0.000(3) -0.004(3) C5 0.019(4) 0.035(3) 0.022(3) 0.004(3) 0.002(3) 0.003(3) C6 0.029(4) 0.036(3) 0.018(3) 0.005(3) 0.006(3) -0.001(3) C7 0.039(4) 0.037(3) 0.013(3) 0.005(3) 0.004(3) 0.005(3) C8 0.025(4) 0.033(4) 0.023(4) 0.006(3) 0.015(3) 0.005(3) C9 0.033(4) 0.039(5) 0.031(4) 0.013(3) 0.010(3) 0.002(3) C10 0.049(4) 0.031(4) 0.045(4) 0.002(4) 0.011(3) -0.005(4) C11 0.036(4) 0.034(4) 0.037(4) -0.009(4) 0.006(3) -0.004(3) C12 0.026(3) 0.037(5) 0.023(4) 0.001(4) 0.013(3) -0.002(3) C13 0.028(3) 0.031(4) 0.022(4) -0.001(4) 0.016(3) 0.003(3) C14 0.030(3) 0.042(3) 0.026(3) 0.002(3) 0.010(3) -0.006(3) C15 0.048(5) 0.035(3) 0.012(4) -0.004(3) 0.007(4) -0.009(3) C16 0.033(4) 0.037(4) 0.022(5) -0.004(3) 0.016(4) 0.005(3) C17 0.061(4) 0.055(4) 0.030(4) -0.001(4) 0.024(4) 0.006(4) C18 0.070(4) 0.072(5) 0.048(4) 0.019(4) 0.031(4) 0.038(4) C19 0.046(4) 0.061(4) 0.040(5) 0.023(3) 0.016(3) 0.029(4) C20 0.041(4) 0.047(4) 0.022(4) 0.011(3) 0.014(4) 0.004(3) C21 0.023(3) 0.030(3) 0.034(5) -0.001(3) 0.011(4) 0.005(3) C28 0.072(4) 0.051(4) 0.065(4) 0.005(4) 0.015(3) -0.009(4) C29 0.054(4) 0.060(5) 0.062(5) 0.003(4) 0.007(3) -0.014(4) C30 0.060(4) 0.061(5) 0.053(4) 0.001(3) 0.024(3) 0.000(3) C31 0.065(4) 0.050(4) 0.047(4) -0.005(3) 0.029(3) 0.005(3) N1 0.027(3) 0.047(3) 0.029(3) 0.005(3) 0.015(3) 0.006(3) O1 0.0465(18) 0.0394(16) 0.0272(17) 0.0031(16) 0.0138(15) 0.0035(15) O2 0.046(2) 0.043(2) 0.0335(18) -0.0078(15) 0.0088(14) 0.0185(16) O3 0.051(2) 0.056(2) 0.021(2) 0.0033(18) 0.014(2) 0.0110(18) O4 0.045(2) 0.054(2) 0.024(2) 0.0075(19) 0.0170(18) 0.013(2) O5 0.051(2) 0.056(3) 0.033(2) 0.0210(19) 0.019(2) 0.0185(18) O6 0.078(3) 0.051(3) 0.032(2) -0.0096(19) 0.025(2) -0.021(2) O7 0.062(3) 0.060(3) 0.054(2) -0.020(2) 0.025(2) -0.009(2) C22A 0.0465(18) 0.0394(16) 0.0272(17) 0.0031(16) 0.0138(15) 0.0035(15) C23A 0.0465(18) 0.0394(16) 0.0272(17) 0.0031(16) 0.0138(15) 0.0035(15) C24A 0.0465(18) 0.0394(16) 0.0272(17) 0.0031(16) 0.0138(15) 0.0035(15) C22B 0.0465(18) 0.0394(16) 0.0272(17) 0.0031(16) 0.0138(15) 0.0035(15) C23B 0.0465(18) 0.0394(16) 0.0272(17) 0.0031(16) 0.0138(15) 0.0035(15) C24B 0.0465(18) 0.0394(16) 0.0272(17) 0.0031(16) 0.0138(15) 0.0035(15) C25A 0.046(2) 0.043(2) 0.0335(18) -0.0078(15) 0.0088(14) 0.0185(16) C26A 0.046(2) 0.043(2) 0.0335(18) -0.0078(15) 0.0088(14) 0.0185(16) C27A 0.046(2) 0.043(2) 0.0335(18) -0.0078(15) 0.0088(14) 0.0185(16) C25B 0.046(2) 0.043(2) 0.0335(18) -0.0078(15) 0.0088(14) 0.0185(16) C26B 0.046(2) 0.043(2) 0.0335(18) -0.0078(15) 0.0088(14) 0.0185(16) C27B 0.046(2) 0.043(2) 0.0335(18) -0.0078(15) 0.0088(14) 0.0185(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C2 1.381(6) . ? C1 C6 1.389(6) . ? C1 N1 1.412(6) . ? C2 C3 1.379(6) . ? C3 C4 1.380(6) . ? C3 C14 1.507(6) . ? C4 C5 1.387(6) . ? C4 O1 1.399(5) . ? C5 C6 1.384(6) . ? C5 C7 1.515(6) . ? C7 C8 1.519(6) . ? C8 C9 1.371(6) . ? C8 C13 1.390(6) . ? C9 C10 1.377(6) . ? C10 C11 1.373(6) . ? C11 C12 1.375(6) 2_656 ? C12 C11 1.376(6) 2_656 ? C12 C13 1.399(6) 2_656 ? C12 C14 1.521(6) . ? C13 O2 1.384(5) . ? C13 C12 1.399(6) 2_656 ? C15 O3 1.259(5) . ? C15 N1 1.340(6) . ? C15 C16 1.498(6) . ? C16 C21 1.390(6) . ? C16 C17 1.394(6) . ? C17 C18 1.384(7) . ? C18 C19 1.373(6) . ? C19 C20 1.371(7) . ? C20 O5 1.364(5) . ? C20 C21 1.395(6) . ? C21 O4 1.365(5) . ? C28 O6 1.399(6) . ? C28 C29 1.502(7) . ? C29 C30 1.479(7) . ? C30 C31 1.519(7) . ? C31 O7 1.420(5) . ? O1 C22B 1.450(16) . ? O1 C22A 1.456(8) . ? O2 C25B 1.372(8) . ? O2 C25A 1.597(13) . ? C22A C23A 1.513(12) . ? C23A C24A 1.499(10) . ? C22B C23B 1.46(2) . ? C23B C24B 1.62(2) . ? C25A C26A 1.505(17) . ? C26A C27A 1.525(13) . ? C25B C26B 1.464(14) . ? C26B C27B 1.539(11) . ? 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 C1 C6 119.8(4) . . ? C2 C1 N1 124.2(5) . . ? C6 C1 N1 116.0(5) . . ? C3 C2 C1 120.4(4) . . ? C2 C3 C4 118.6(4) . . ? C2 C3 C14 120.5(5) . . ? C4 C3 C14 120.5(5) . . ? C3 C4 C5 122.4(4) . . ? C3 C4 O1 118.5(5) . . ? C5 C4 O1 118.7(5) . . ? C6 C5 C4 117.6(4) . . ? C6 C5 C7 120.3(5) . . ? C4 C5 C7 121.7(5) . . ? C5 C6 C1 120.8(4) . . ? C5 C7 C8 109.8(4) . . ? C9 C8 C13 117.8(4) . . ? C9 C8 C7 119.8(5) . . ? C13 C8 C7 122.2(5) . . ? C8 C9 C10 122.0(5) . . ? C11 C10 C9 118.9(5) . . ? C10 C11 C12 121.7(5) . 2_656 ? C11 C12 C13 117.8(4) 2_656 2_656 ? C11 C12 C14 120.6(5) 2_656 . ? C13 C12 C14 121.6(5) 2_656 . ? O2 C13 C8 120.1(5) . . ? O2 C13 C12 118.3(5) . 2_656 ? C8 C13 C12 121.5(4) . 2_656 ? C3 C14 C12 110.9(4) . . ? O3 C15 N1 123.2(5) . . ? O3 C15 C16 118.9(6) . . ? N1 C15 C16 117.9(5) . . ? C21 C16 C17 117.4(5) . . ? C21 C16 C15 125.5(5) . . ? C17 C16 C15 117.1(6) . . ? C18 C17 C16 121.3(5) . . ? C19 C18 C17 120.3(5) . . ? C20 C19 C18 119.8(5) . . ? O5 C20 C19 123.7(5) . . ? O5 C20 C21 116.2(5) . . ? C19 C20 C21 120.1(5) . . ? O4 C21 C16 119.7(5) . . ? O4 C21 C20 119.2(5) . . ? C16 C21 C20 121.1(5) . . ? O6 C28 C29 114.8(4) . . ? C30 C29 C28 114.4(5) . . ? C29 C30 C31 115.9(5) . . ? O7 C31 C30 112.2(4) . . ? C15 N1 C1 129.4(4) . . ? C4 O1 C22B 111.2(7) . . ? C4 O1 C22A 117.5(4) . . ? C25B O2 C13 122.8(5) . . ? C13 O2 C25A 100.7(5) . . ? O1 C22A C23A 111.4(6) . . ? C24A C23A C22A 108.6(6) . . ? O1 C22B C23B 109.9(13) . . ? C22B C23B C24B 116.1(13) . . ? C26A C25A O2 103.6(9) . . ? C25A C26A C27A 113.1(11) . . ? O2 C25B C26B 110.9(8) . . ? C25B C26B C27B 111.8(8) . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 956153'