# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_2004uv01 _database_code_depnum_ccdc_archive 'CCDC 662956' _audit_creation_date 2004-03-26T19:48:31-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 2004uv01cj01 _chemical_formula_moiety 'C15 H14 O3, H2 O' _chemical_formula_sum 'C15 H16 O4' _chemical_formula_weight 260.28 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/n' _symmetry_space_group_name_Hall '-P 2yac' _symmetry_Int_Tables_number 13 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 14.2980(10) _cell_length_b 5.6536(5) _cell_length_c 17.4704(14) _cell_angle_alpha 90 _cell_angle_beta 111.057(4) _cell_angle_gamma 90 _cell_volume 1317.92(19) _cell_formula_units_Z 4 _cell_measurement_temperature 120.0(1) _cell_measurement_reflns_used 2351 _cell_measurement_theta_min 0.999 _cell_measurement_theta_max 68.251 _cell_measurement_wavelength 1.5418 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.782 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.543 _exptl_absorpt_correction_T_max 0.939 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120.0(1) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator 'multilayer graded optic' _diffrn_radiation_probe x-ray _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.0100519 _diffrn_orient_matrix_ub_12 0.1223683 _diffrn_orient_matrix_ub_13 -0.037656 _diffrn_orient_matrix_ub_21 0.0337393 _diffrn_orient_matrix_ub_22 0.105293 _diffrn_orient_matrix_ub_23 0.048017 _diffrn_orient_matrix_ub_31 0.0661607 _diffrn_orient_matrix_ub_32 -0.0722867 _diffrn_orient_matrix_ub_33 0.006197 _diffrn_measurement_device '135mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD2000 _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.046 _diffrn_reflns_av_unetI/netI 0.0289 _diffrn_reflns_number 11513 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.98 _diffrn_reflns_theta_max 68.36 _diffrn_reflns_theta_full 68.37 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _reflns_number_total 2376 _reflns_number_gt 2105 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^)+(0.0836P)^2^+0.3751P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0072(13) _refine_ls_number_reflns 2376 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1363 _refine_ls_wR_factor_gt 0.1312 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.206 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.051 #----------------------------------------------------------------------------# # 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 0.0181 0.0091 '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' O O 0.0492 0.0322 '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 O1 O 0.55530(8) 0.2869(2) 0.19791(7) 0.0328(3) Uani 1 1 d . . . C1 C 0.45516(11) 0.3268(3) 0.15586(9) 0.0278(4) Uani 1 1 d . . . C2 C 0.38617(11) 0.2064(3) 0.18126(9) 0.0274(4) Uani 1 1 d . . . C3 C 0.28445(12) 0.2399(3) 0.13531(9) 0.0308(4) Uani 1 1 d . . . C4 C 0.25289(12) 0.3912(3) 0.06851(9) 0.0318(4) Uani 1 1 d . . . C5 C 0.32237(11) 0.5145(3) 0.04495(9) 0.0289(4) Uani 1 1 d . . . C6 C 0.42395(11) 0.4800(3) 0.08885(9) 0.0285(4) Uani 1 1 d . . . C7 C 0.41679(11) 0.0491(3) 0.25473(9) 0.0273(4) Uani 1 1 d . . . C8 C 0.48791(11) 0.1208(3) 0.32967(9) 0.0298(4) Uani 1 1 d . . . C9 C 0.50960(12) -0.0217(3) 0.39860(10) 0.0343(4) Uani 1 1 d . . . C10 C 0.46132(12) -0.2379(3) 0.39366(10) 0.0356(4) Uani 1 1 d . . . C11 C 0.39183(12) -0.3114(3) 0.31947(10) 0.0347(4) Uani 1 1 d . . . C12 C 0.36998(12) -0.1696(3) 0.25026(10) 0.0310(4) Uani 1 1 d . . . C13 C 0.28601(12) 0.6775(3) -0.02980(9) 0.0320(4) Uani 1 1 d . . . C14 C 0.35817(14) 0.8740(3) -0.03106(11) 0.0375(4) Uani 1 1 d . . . C15 C 0.26074(11) 0.5181(3) -0.10464(9) 0.0294(4) Uani 1 1 d . . . O16 O 0.17216(8) 0.4215(2) -0.12528(7) 0.0364(3) Uani 1 1 d . . . O17 O 0.31924(8) 0.4757(2) -0.13971(7) 0.0365(3) Uani 1 1 d . . . O1W O 0.64441(15) -0.1514(3) 0.25081(10) 0.0679(5) Uani 1 1 d . . . H13 H 0.2197(14) 0.754(4) -0.0318(12) 0.039(5) Uiso 1 1 d . . . H14A H 0.3740(15) 0.978(4) 0.0181(13) 0.045(5) Uiso 1 1 d . . . H12 H 0.3203(14) -0.223(3) 0.1964(12) 0.036(5) Uiso 1 1 d . . . H3 H 0.2343(14) 0.153(4) 0.1524(11) 0.037(5) Uiso 1 1 d . . . H9 H 0.5609(14) 0.034(4) 0.4527(13) 0.039(5) Uiso 1 1 d . . . H6 H 0.4738(14) 0.565(3) 0.0719(11) 0.035(5) Uiso 1 1 d . . . H8 H 0.5217(14) 0.273(4) 0.3347(12) 0.039(5) Uiso 1 1 d . . . H14C H 0.4243(15) 0.809(3) -0.0339(12) 0.037(5) Uiso 1 1 d . . . H14B H 0.3264(15) 0.982(4) -0.0805(13) 0.049(6) Uiso 1 1 d . . . H4 H 0.1791(15) 0.409(4) 0.0363(11) 0.041(5) Uiso 1 1 d . . . H10 H 0.4772(15) -0.341(4) 0.4462(13) 0.046(5) Uiso 1 1 d . . . H11 H 0.3590(14) -0.464(4) 0.3136(11) 0.038(5) Uiso 1 1 d . . . H1WB H 0.612(2) -0.015(5) 0.2354(16) 0.071(8) Uiso 1 1 d . . . H1WA H 0.668(2) -0.199(6) 0.216(2) 0.094(10) Uiso 1 1 d . . . H16 H 0.1578(19) 0.327(5) -0.1749(17) 0.070(7) Uiso 1 1 d . . . H1O H 0.5906(17) 0.361(4) 0.1727(14) 0.057(6) 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 0.0263(6) 0.0383(7) 0.0366(6) 0.0077(5) 0.0148(5) 0.0006(5) C1 0.0255(7) 0.0303(8) 0.0298(7) -0.0015(6) 0.0126(6) 0.0007(6) C2 0.0297(8) 0.0287(8) 0.0281(7) -0.0021(6) 0.0155(6) -0.0009(6) C3 0.0284(8) 0.0369(9) 0.0310(8) -0.0018(6) 0.0155(6) -0.0021(7) C4 0.0279(8) 0.0392(9) 0.0301(8) -0.0004(6) 0.0128(6) 0.0013(7) C5 0.0315(8) 0.0303(8) 0.0274(7) -0.0021(6) 0.0136(6) 0.0017(6) C6 0.0294(8) 0.0292(8) 0.0303(8) -0.0009(6) 0.0148(6) -0.0018(6) C7 0.0257(7) 0.0296(8) 0.0323(8) 0.0000(6) 0.0173(6) 0.0019(6) C8 0.0290(8) 0.0322(9) 0.0329(8) -0.0011(6) 0.0165(6) 0.0003(7) C9 0.0315(8) 0.0409(10) 0.0332(8) 0.0029(7) 0.0147(7) 0.0031(7) C10 0.0358(9) 0.0383(10) 0.0382(9) 0.0089(7) 0.0201(7) 0.0055(7) C11 0.0359(8) 0.0304(9) 0.0453(9) 0.0026(7) 0.0237(7) 0.0011(7) C12 0.0308(8) 0.0322(9) 0.0346(8) -0.0013(6) 0.0174(7) 0.0004(6) C13 0.0329(8) 0.0327(9) 0.0316(8) 0.0016(6) 0.0129(6) 0.0031(7) C14 0.0459(10) 0.0325(9) 0.0352(9) 0.0007(7) 0.0160(7) -0.0018(8) C15 0.0264(7) 0.0325(9) 0.0291(8) 0.0064(6) 0.0098(6) 0.0014(6) O16 0.0272(6) 0.0475(8) 0.0362(6) -0.0035(5) 0.0135(5) -0.0055(5) O17 0.0344(6) 0.0449(7) 0.0368(6) -0.0049(5) 0.0208(5) -0.0071(5) O1W 0.1061(13) 0.0582(10) 0.0622(10) 0.0261(8) 0.0579(10) 0.0458(10) #----------------------------------------------------------------------------# # 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 1.3728(18) . ? O1 H1O 0.88(3) . ? C1 C6 1.394(2) . ? C1 C2 1.396(2) . ? C2 C3 1.399(2) . ? C2 C7 1.492(2) . ? C3 C4 1.385(2) . ? C3 H3 1.00(2) . ? C4 C5 1.391(2) . ? C4 H4 1.006(19) . ? C5 C6 1.391(2) . ? C5 C13 1.529(2) . ? C6 H6 0.99(2) . ? C7 C12 1.395(2) . ? C7 C8 1.398(2) . ? C8 C9 1.388(2) . ? C8 H8 0.97(2) . ? C9 C10 1.391(3) . ? C9 H9 1.01(2) . ? C10 C11 1.384(2) . ? C10 H10 1.04(2) . ? C11 C12 1.389(2) . ? C11 H11 0.97(2) . ? C12 H12 1.00(2) . ? C13 C15 1.521(2) . ? C13 C14 1.522(2) . ? C13 H13 1.03(2) . ? C14 H14A 1.00(2) . ? C14 H14C 1.03(2) . ? C14 H14B 1.02(2) . ? C15 O17 1.2249(19) . ? C15 O16 1.3053(19) . ? O16 H16 0.98(3) . ? O1W H1WB 0.89(3) . ? O1W H1WA 0.83(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 C1 O1 H1O 109.1(15) . . ? O1 C1 C6 120.59(13) . . ? O1 C1 C2 118.05(13) . . ? C6 C1 C2 121.35(14) . . ? C1 C2 C3 117.36(14) . . ? C1 C2 C7 122.81(13) . . ? C3 C2 C7 119.83(13) . . ? C4 C3 C2 121.59(14) . . ? C4 C3 H3 120.3(11) . . ? C2 C3 H3 118.1(11) . . ? C3 C4 C5 120.49(14) . . ? C3 C4 H4 119.4(11) . . ? C5 C4 H4 120.1(11) . . ? C6 C5 C4 118.80(14) . . ? C6 C5 C13 121.51(14) . . ? C4 C5 C13 119.66(13) . . ? C5 C6 C1 120.38(14) . . ? C5 C6 H6 119.3(11) . . ? C1 C6 H6 120.3(11) . . ? C12 C7 C8 118.83(14) . . ? C12 C7 C2 119.59(13) . . ? C8 C7 C2 121.49(14) . . ? C9 C8 C7 120.32(15) . . ? C9 C8 H8 119.0(11) . . ? C7 C8 H8 120.6(11) . . ? C8 C9 C10 120.31(15) . . ? C8 C9 H9 119.3(12) . . ? C10 C9 H9 120.3(11) . . ? C11 C10 C9 119.69(15) . . ? C11 C10 H10 121.0(12) . . ? C9 C10 H10 119.3(11) . . ? C10 C11 C12 120.21(16) . . ? C10 C11 H11 121.5(11) . . ? C12 C11 H11 118.2(11) . . ? C11 C12 C7 120.61(15) . . ? C11 C12 H12 120.5(11) . . ? C7 C12 H12 118.9(11) . . ? C15 C13 C14 111.91(13) . . ? C15 C13 C5 106.24(13) . . ? C14 C13 C5 115.36(13) . . ? C15 C13 H13 106.7(11) . . ? C14 C13 H13 108.3(11) . . ? C5 C13 H13 107.9(11) . . ? C13 C14 H14A 111.3(12) . . ? C13 C14 H14C 112.2(11) . . ? H14A C14 H14C 108.9(16) . . ? C13 C14 H14B 110.5(12) . . ? H14A C14 H14B 105.8(16) . . ? H14C C14 H14B 107.9(16) . . ? O17 C15 O16 123.32(15) . . ? O17 C15 C13 123.49(14) . . ? O16 C15 C13 113.11(13) . . ? C15 O16 H16 110.4(15) . . ? H1WB O1W H1WA 111(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -176.89(13) . . . . ? C6 C1 C2 C3 1.9(2) . . . . ? O1 C1 C2 C7 3.8(2) . . . . ? C6 C1 C2 C7 -177.38(13) . . . . ? C1 C2 C3 C4 -1.7(2) . . . . ? C7 C2 C3 C4 177.61(14) . . . . ? C2 C3 C4 C5 0.3(2) . . . . ? C3 C4 C5 C6 1.0(2) . . . . ? C3 C4 C5 C13 179.02(14) . . . . ? C4 C5 C6 C1 -0.8(2) . . . . ? C13 C5 C6 C1 -178.77(14) . . . . ? O1 C1 C6 C5 178.09(14) . . . . ? C2 C1 C6 C5 -0.7(2) . . . . ? C1 C2 C7 C12 -136.10(16) . . . . ? C3 C2 C7 C12 44.6(2) . . . . ? C1 C2 C7 C8 47.3(2) . . . . ? C3 C2 C7 C8 -131.97(16) . . . . ? C12 C7 C8 C9 -1.4(2) . . . . ? C2 C7 C8 C9 175.20(13) . . . . ? C7 C8 C9 C10 0.5(2) . . . . ? C8 C9 C10 C11 0.4(2) . . . . ? C9 C10 C11 C12 -0.3(2) . . . . ? C10 C11 C12 C7 -0.7(2) . . . . ? C8 C7 C12 C11 1.5(2) . . . . ? C2 C7 C12 C11 -175.15(14) . . . . ? C6 C5 C13 C15 98.66(16) . . . . ? C4 C5 C13 C15 -79.28(17) . . . . ? C6 C5 C13 C14 -26.0(2) . . . . ? C4 C5 C13 C14 156.10(15) . . . . ? C14 C13 C15 O17 31.6(2) . . . . ? C5 C13 C15 O17 -95.11(17) . . . . ? C14 C13 C15 O16 -151.58(14) . . . . ? C5 C13 C15 O16 81.69(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WB O1 0.89(3) 1.90(3) 2.7878(19) 173(2) . O1W H1WA O17 0.83(4) 2.11(4) 2.851(2) 148(3) 3_655 O16 H16 O1W 0.98(3) 1.59(3) 2.5610(18) 173(2) 4 O1 H1O O17 0.88(3) 1.84(3) 2.7134(16) 169(2) 3_665 data_uv02cja1n _database_code_depnum_ccdc_archive 'CCDC 910283' #TrackingRef '15321_web_deposit_cif_file_0_IgnacioVaya_1352455175.ccdc_deposit.cif' _audit_creation_date 2010-11-08T10:09:45-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common S-FBPOHMe _chemical_formula_moiety 'C16 H16 O3' _chemical_formula_sum 'C16 H16 O3' _chemical_formula_weight 256.29 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 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' _cell_length_a 8.0469(7) _cell_length_b 20.6366(15) _cell_length_c 32.852(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 5455.4(8) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1939 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 21.03 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.94 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7878 _exptl_absorpt_correction_T_max 0.9748 _exptl_absorpt_process_details 'BRUKER AXS - SADABS' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Bruker X8 kappa APEXII CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.1438 _diffrn_reflns_av_sigmaI/netI 0.0642 _diffrn_reflns_number 45355 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 20.81 _diffrn_reflns_theta_full 20.81 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3259 _reflns_number_gt 2479 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 v2010.9-1 (Bruker AXS, 2010)' _computing_cell_refinement 'APEX2 v2010.9-1 (Bruker AXS, 2010)' _computing_data_reduction 'APEX2 v2010.9-1 (Bruker AXS, 2010)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(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^)+(0.0474P)^2^+2.7006P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3259 _refine_ls_number_parameters 705 _refine_ls_number_restraints 470 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 0.962 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.210 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.050 #----------------------------------------------------------------------------# # 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' 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 C1 C 0.5345(7) 0.0189(3) 0.23731(17) 0.0153(15) Uani 1 1 d DU . . C2 C 0.5109(7) 0.0374(3) 0.27801(16) 0.0149(14) Uani 1 1 d DU . . C3 C 0.3484(7) 0.0500(3) 0.29012(17) 0.0180(15) Uani 1 1 d DU . . H3 H 0.3283 0.0640 0.3172 0.022 Uiso 1 1 calc R . . C4 C 0.2154(8) 0.0428(2) 0.26401(17) 0.0176(15) Uani 1 1 d DU . . H4 H 0.1061 0.0515 0.2734 0.021 Uiso 1 1 calc R . . C5 C 0.2399(7) 0.0227(3) 0.22380(17) 0.0169(15) Uani 1 1 d DU . . C6 C 0.4022(7) 0.0108(2) 0.21108(17) 0.0128(14) Uani 1 1 d DU . . H6 H 0.4220 -0.0032 0.1840 0.015 Uiso 1 1 calc R . . O7 O 0.6959(5) 0.0096(2) 0.22454(12) 0.0215(12) Uani 1 1 d DU . . H7 H 0.701(8) 0.004(3) 0.1998(16) 0.026 Uiso 1 1 d . . . C8 C 0.6527(7) 0.0449(3) 0.30664(17) 0.0175(15) Uani 1 1 d DU . . C9 C 0.7714(7) -0.0034(3) 0.31170(16) 0.0210(16) Uani 1 1 d DU . . H9 H 0.7633 -0.0421 0.2962 0.025 Uiso 1 1 calc R . . C10 C 0.9021(8) 0.0042(3) 0.33913(17) 0.0272(17) Uani 1 1 d DU . . H10 H 0.9817 -0.0293 0.3426 0.033 Uiso 1 1 calc R . . C11 C 0.9149(8) 0.0610(3) 0.36127(18) 0.0263(17) Uani 1 1 d DU . . H11 H 1.0039 0.0667 0.3800 0.032 Uiso 1 1 calc R . . C12 C 0.7989(9) 0.1091(3) 0.35621(18) 0.0300(18) Uani 1 1 d DU . . H12 H 0.8092 0.1484 0.3711 0.036 Uiso 1 1 calc R . . C13 C 0.6677(8) 0.1008(3) 0.32974(17) 0.0245(17) Uani 1 1 d DU . . H13 H 0.5863 0.1340 0.3273 0.029 Uiso 1 1 calc R . . C14 C 0.0937(7) 0.0110(3) 0.19572(16) 0.0172(15) Uani 1 1 d DU . . H14 H -0.0009 0.0389 0.2048 0.021 Uiso 1 1 calc R . . C15 C 0.1413(8) 0.0303(3) 0.15319(18) 0.0204(16) Uani 1 1 d DU . . O16 O 0.1776(6) -0.0071(2) 0.12596(12) 0.0330(12) Uani 1 1 d DU . . O17 O 0.1470(6) 0.09426(19) 0.14871(12) 0.0355(13) Uani 1 1 d DU . . C18 C 0.2040(10) 0.1185(4) 0.10877(19) 0.060(3) Uani 1 1 d DU . . H18A H 0.3175 0.1033 0.1037 0.090 Uiso 1 1 calc R . . H18B H 0.2021 0.1659 0.1088 0.090 Uiso 1 1 calc R . . H18C H 0.1302 0.1022 0.0874 0.090 Uiso 1 1 calc R . . C19 C 0.0377(8) -0.0598(2) 0.19705(17) 0.0209(16) Uani 1 1 d DU . . H19A H 0.1310 -0.0880 0.1896 0.031 Uiso 1 1 calc R . . H19B H -0.0539 -0.0663 0.1778 0.031 Uiso 1 1 calc R . . H19C H 0.0003 -0.0706 0.2246 0.031 Uiso 1 1 calc R . . C21 C 0.0391(7) 0.2666(3) 0.35274(17) 0.0143(15) Uani 1 1 d DU . . C22 C 0.0692(7) 0.2461(2) 0.39252(16) 0.0119(14) Uani 1 1 d DU . . C23 C 0.2334(7) 0.2337(3) 0.40298(17) 0.0159(15) Uani 1 1 d DU . . H23 H 0.2569 0.2182 0.4296 0.019 Uiso 1 1 calc R . . C24 C 0.3644(8) 0.2430(3) 0.37630(16) 0.0197(16) Uani 1 1 d DU . . H24 H 0.4749 0.2336 0.3846 0.024 Uiso 1 1 calc R . . C25 C 0.3327(7) 0.2664(3) 0.33706(16) 0.0146(15) Uani 1 1 d DU . . C26 C 0.1688(7) 0.2778(3) 0.32577(18) 0.0155(15) Uani 1 1 d DU . . H26 H 0.1452 0.2935 0.2992 0.019 Uiso 1 1 calc R . . O27 O -0.1228(6) 0.2768(2) 0.34084(12) 0.0209(12) Uani 1 1 d DU . . H27 H -0.129(8) 0.283(3) 0.3175(17) 0.025 Uiso 1 1 d . . . C28 C -0.0647(7) 0.2372(3) 0.42302(17) 0.0166(15) Uani 1 1 d DU . . C29 C -0.1903(8) 0.2831(3) 0.42810(18) 0.0226(16) Uani 1 1 d DU . . H29 H -0.1925 0.3201 0.4108 0.027 Uiso 1 1 calc R . . C30 C -0.3119(9) 0.2763(3) 0.45765(17) 0.0261(17) Uani 1 1 d DU . . H30 H -0.3951 0.3085 0.4608 0.031 Uiso 1 1 calc R . . C31 C -0.3114(8) 0.2222(3) 0.48259(17) 0.0249(17) Uani 1 1 d DU . . H31 H -0.3957 0.2167 0.5025 0.030 Uiso 1 1 calc R . . C32 C -0.1882(8) 0.1765(3) 0.47832(17) 0.0219(16) Uani 1 1 d DU . . H32 H -0.1866 0.1396 0.4956 0.026 Uiso 1 1 calc R . . C33 C -0.0669(8) 0.1839(3) 0.44897(16) 0.0164(15) Uani 1 1 d DU . . H33 H 0.0172 0.1519 0.4464 0.020 Uiso 1 1 calc R . . C34 C 0.4753(7) 0.2854(3) 0.30944(16) 0.0173(15) Uani 1 1 d DU . . H34 H 0.5753 0.2595 0.3174 0.021 Uiso 1 1 calc R . . C35 C 0.4340(8) 0.2704(3) 0.26567(17) 0.0157(15) Uani 1 1 d DU . . O36 O 0.4009(5) 0.31016(18) 0.23949(12) 0.0227(11) Uani 1 1 d DU . . O37 O 0.4384(5) 0.20701(17) 0.25817(12) 0.0241(11) Uani 1 1 d DU . . C38 C 0.3921(9) 0.1869(3) 0.21746(16) 0.0277(18) Uani 1 1 d DU . . H38A H 0.2804 0.2029 0.2112 0.042 Uiso 1 1 calc R . . H38B H 0.3932 0.1395 0.2159 0.042 Uiso 1 1 calc R . . H38C H 0.4716 0.2047 0.1978 0.042 Uiso 1 1 calc R . . C39 C 0.5168(8) 0.3571(2) 0.31412(17) 0.0191(16) Uani 1 1 d DU . . H39A H 0.4173 0.3831 0.3087 0.029 Uiso 1 1 calc R . . H39B H 0.6043 0.3689 0.2947 0.029 Uiso 1 1 calc R . . H39C H 0.5555 0.3654 0.3419 0.029 Uiso 1 1 calc R . . C41 C 0.3705(7) -0.0271(3) 0.02983(17) 0.0163(15) Uani 1 1 d DU . . C42 C 0.3926(7) -0.0139(3) -0.01162(16) 0.0183(15) Uani 1 1 d DU . . C43 C 0.5548(7) -0.0014(3) -0.02460(17) 0.0183(15) Uani 1 1 d DU . . H43 H 0.5742 0.0082 -0.0525 0.022 Uiso 1 1 calc R . . C44 C 0.6882(8) -0.0025(3) 0.00208(16) 0.0163(15) Uani 1 1 d DU . . H44 H 0.7970 0.0062 -0.0077 0.020 Uiso 1 1 calc R . . C45 C 0.6640(7) -0.0163(3) 0.04300(17) 0.0180(15) Uani 1 1 d DU . . C46 C 0.5037(7) -0.0288(3) 0.05606(18) 0.0173(15) Uani 1 1 d DU . . H46 H 0.4851 -0.0390 0.0839 0.021 Uiso 1 1 calc R . . O47 O 0.2111(6) -0.0374(2) 0.04359(12) 0.0296(13) Uani 1 1 d DU . . H47 H 0.210(8) -0.032(3) 0.0683(18) 0.036 Uiso 1 1 d . . . C48 C 0.2503(7) -0.0106(3) -0.04007(16) 0.0157(15) Uani 1 1 d DU . . C49 C 0.1369(8) -0.0609(3) -0.04303(17) 0.0209(16) Uani 1 1 d DU . . H49 H 0.1506 -0.0983 -0.0265 0.025 Uiso 1 1 calc R . . C50 C 0.0041(8) -0.0575(3) -0.06970(17) 0.0234(17) Uani 1 1 d DU . . H50 H -0.0704 -0.0930 -0.0722 0.028 Uiso 1 1 calc R . . C51 C -0.0195(8) -0.0021(3) -0.09262(17) 0.0236(17) Uani 1 1 d DU . . H51 H -0.1126 0.0008 -0.1103 0.028 Uiso 1 1 calc R . . C52 C 0.0907(8) 0.0488(3) -0.09006(17) 0.0247(17) Uani 1 1 d DU . . H52 H 0.0739 0.0868 -0.1058 0.030 Uiso 1 1 calc R . . C53 C 0.2268(8) 0.0441(3) -0.06418(16) 0.0207(16) Uani 1 1 d DU . . H53 H 0.3047 0.0786 -0.0629 0.025 Uiso 1 1 calc R . . C54 C 0.8122(8) -0.0207(3) 0.07198(16) 0.0194(15) Uani 1 1 d DU . . H54 H 0.9132 -0.0037 0.0579 0.023 Uiso 1 1 calc R . . C55 C 0.7730(8) 0.0225(3) 0.10769(18) 0.0178(15) Uani 1 1 d DU . . O56 O 0.7211(5) 0.00414(19) 0.14059(12) 0.0238(11) Uani 1 1 d DU . . O57 O 0.7977(6) 0.08497(17) 0.09899(11) 0.0270(12) Uani 1 1 d DU . . C58 C 0.7527(9) 0.1313(3) 0.13099(19) 0.042(2) Uani 1 1 d DU . . H58A H 0.6348 0.1262 0.1378 0.063 Uiso 1 1 calc R . . H58B H 0.7728 0.1755 0.1213 0.063 Uiso 1 1 calc R . . H58C H 0.8203 0.1231 0.1553 0.063 Uiso 1 1 calc R . . C59 C 0.8452(9) -0.0909(2) 0.08543(17) 0.0249(17) Uani 1 1 d DU . . H59A H 0.7481 -0.1075 0.1001 0.037 Uiso 1 1 calc R . . H59B H 0.9426 -0.0921 0.1033 0.037 Uiso 1 1 calc R . . H59C H 0.8659 -0.1179 0.0614 0.037 Uiso 1 1 calc R . . C61 C 0.2215(7) 0.3150(3) 0.14083(17) 0.0160(15) Uani 1 1 d DU . . C62 C 0.1923(7) 0.3098(3) 0.09874(16) 0.0157(14) Uani 1 1 d DU . . C63 C 0.0289(8) 0.3079(3) 0.08667(18) 0.0185(15) Uani 1 1 d DU . . H63 H 0.0051 0.3056 0.0584 0.022 Uiso 1 1 calc R . . C64 C -0.1028(8) 0.3091(3) 0.11381(16) 0.0154(15) Uani 1 1 d DU . . H64 H -0.2138 0.3067 0.1041 0.018 Uiso 1 1 calc R . . C65 C -0.0720(7) 0.3138(3) 0.15549(16) 0.0128(14) Uani 1 1 d DU . . C66 C 0.0916(7) 0.3176(3) 0.16832(17) 0.0170(15) Uani 1 1 d DU . . H66 H 0.1150 0.3220 0.1965 0.020 Uiso 1 1 calc R . . O67 O 0.3841(6) 0.3188(2) 0.15354(12) 0.0231(12) Uani 1 1 d DU . . H67 H 0.391(9) 0.325(3) 0.1755(18) 0.028 Uiso 1 1 d . . . C68 C 0.3289(7) 0.3060(3) 0.06818(16) 0.0169(15) Uani 1 1 d DU . . C69 C 0.4614(8) 0.2637(3) 0.07194(18) 0.0227(16) Uani 1 1 d DU . . H69 H 0.4704 0.2375 0.0956 0.027 Uiso 1 1 calc R . . C70 C 0.5816(8) 0.2588(3) 0.04168(18) 0.0284(17) Uani 1 1 d DU . . H70 H 0.6703 0.2287 0.0446 0.034 Uiso 1 1 calc R . . C71 C 0.5724(8) 0.2975(3) 0.00742(19) 0.0286(17) Uani 1 1 d DU . . H71 H 0.6557 0.2947 -0.0130 0.034 Uiso 1 1 calc R . . C72 C 0.4421(8) 0.3398(3) 0.00314(18) 0.0279(17) Uani 1 1 d DU . . H72 H 0.4356 0.3665 -0.0204 0.034 Uiso 1 1 calc R . . C73 C 0.3191(8) 0.3440(3) 0.03296(16) 0.0209(16) Uani 1 1 d DU . . H73 H 0.2281 0.3728 0.0293 0.025 Uiso 1 1 calc R . . C74 C -0.2144(7) 0.3177(2) 0.18546(15) 0.0150(15) Uani 1 1 d DU . . H74 H -0.3155 0.2995 0.1719 0.018 Uiso 1 1 calc R . . C75 C -0.1782(7) 0.2770(3) 0.22248(18) 0.0142(15) Uani 1 1 d DU . . O76 O -0.1475(5) 0.29751(18) 0.25591(13) 0.0227(11) Uani 1 1 d DU . . O77 O -0.1829(6) 0.21387(17) 0.21378(11) 0.0224(11) Uani 1 1 d DU . . C78 C -0.1418(9) 0.1700(3) 0.24742(18) 0.0333(19) Uani 1 1 d DU . . H78A H -0.0244 0.1751 0.2547 0.050 Uiso 1 1 calc R . . H78B H -0.1624 0.1251 0.2390 0.050 Uiso 1 1 calc R . . H78C H -0.2112 0.1804 0.2711 0.050 Uiso 1 1 calc R . . C79 C -0.2521(8) 0.3881(2) 0.19723(17) 0.0197(16) Uani 1 1 d DU . . H79A H -0.3408 0.3890 0.2177 0.030 Uiso 1 1 calc R . . H79B H -0.2878 0.4122 0.1730 0.030 Uiso 1 1 calc R . . H79C H -0.1518 0.4082 0.2085 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.013(4) 0.016(3) 0.018(4) -0.006(3) 0.002(3) -0.002(3) C2 0.017(4) 0.011(3) 0.016(4) -0.001(3) 0.001(3) -0.004(3) C3 0.025(4) 0.016(3) 0.013(4) -0.005(3) 0.007(3) -0.002(3) C4 0.019(4) 0.014(3) 0.020(4) 0.004(3) 0.000(3) -0.003(3) C5 0.019(4) 0.013(3) 0.019(3) 0.001(3) -0.002(3) 0.001(3) C6 0.017(4) 0.011(3) 0.010(3) -0.003(3) 0.000(3) 0.004(3) O7 0.017(3) 0.036(3) 0.011(2) -0.005(2) -0.004(2) 0.000(2) C8 0.021(4) 0.017(3) 0.015(4) 0.001(3) 0.004(3) -0.005(3) C9 0.028(4) 0.023(3) 0.012(4) -0.003(3) 0.000(3) 0.000(3) C10 0.018(4) 0.049(4) 0.015(4) -0.003(3) 0.001(3) 0.008(4) C11 0.017(4) 0.045(4) 0.016(4) 0.000(3) -0.004(3) -0.011(4) C12 0.046(5) 0.026(4) 0.017(4) 0.004(3) -0.002(4) -0.019(4) C13 0.031(5) 0.025(4) 0.018(4) -0.001(3) -0.003(3) -0.003(3) C14 0.013(4) 0.020(3) 0.019(3) 0.003(3) -0.003(3) 0.006(3) C15 0.009(4) 0.029(4) 0.024(4) 0.008(3) -0.008(3) -0.002(4) O16 0.031(3) 0.050(3) 0.018(3) -0.003(2) 0.001(2) -0.006(3) O17 0.041(3) 0.026(3) 0.040(3) 0.016(2) -0.012(3) -0.012(3) C18 0.054(6) 0.083(6) 0.043(5) 0.046(4) -0.012(5) -0.032(5) C19 0.019(4) 0.020(3) 0.024(4) 0.001(3) 0.002(3) -0.004(3) C21 0.010(4) 0.011(3) 0.022(4) -0.003(3) -0.005(3) 0.001(3) C22 0.017(4) 0.005(3) 0.013(3) -0.004(3) -0.004(3) -0.005(3) C23 0.019(4) 0.021(3) 0.008(3) 0.004(3) -0.007(3) 0.001(3) C24 0.014(4) 0.030(4) 0.015(4) 0.002(3) -0.001(3) 0.004(3) C25 0.017(4) 0.008(3) 0.019(4) -0.006(3) 0.002(3) -0.005(3) C26 0.017(4) 0.017(3) 0.012(4) 0.006(3) -0.004(3) -0.004(3) O27 0.016(3) 0.034(3) 0.012(2) 0.006(2) -0.004(2) -0.002(2) C28 0.015(4) 0.016(3) 0.019(4) -0.003(3) 0.000(3) 0.000(3) C29 0.024(4) 0.025(4) 0.019(4) 0.002(3) -0.006(3) -0.002(3) C30 0.031(5) 0.022(4) 0.026(4) -0.008(3) 0.005(4) 0.000(3) C31 0.021(4) 0.034(4) 0.019(4) -0.004(3) 0.009(3) -0.008(3) C32 0.029(5) 0.021(3) 0.016(4) 0.003(3) -0.001(3) -0.012(3) C33 0.023(4) 0.010(3) 0.016(4) -0.003(3) -0.003(3) 0.002(3) C34 0.014(4) 0.019(3) 0.019(3) -0.003(3) -0.003(3) -0.004(3) C35 0.010(4) 0.016(3) 0.022(4) 0.001(3) 0.002(3) 0.000(3) O36 0.030(3) 0.017(2) 0.021(3) 0.002(2) -0.001(2) -0.001(2) O37 0.037(3) 0.014(2) 0.022(3) -0.0024(19) -0.004(2) 0.003(2) C38 0.042(5) 0.016(3) 0.025(4) -0.002(3) -0.003(4) -0.005(4) C39 0.020(4) 0.028(3) 0.009(4) 0.000(3) -0.001(3) -0.004(3) C41 0.009(4) 0.020(3) 0.020(4) -0.002(3) 0.000(3) 0.001(3) C42 0.023(4) 0.018(4) 0.014(3) -0.004(3) -0.004(3) 0.002(3) C43 0.020(4) 0.022(4) 0.012(4) -0.004(3) 0.002(3) 0.004(3) C44 0.013(4) 0.017(3) 0.019(3) 0.004(3) 0.002(3) -0.002(3) C45 0.016(4) 0.020(4) 0.018(3) -0.010(3) 0.002(3) -0.004(3) C46 0.019(4) 0.025(4) 0.007(4) 0.005(3) 0.002(3) 0.000(3) O47 0.018(3) 0.061(3) 0.010(2) -0.001(2) -0.003(2) -0.002(3) C48 0.016(4) 0.021(3) 0.010(3) -0.005(3) 0.000(3) -0.003(3) C49 0.032(4) 0.019(3) 0.012(4) 0.000(3) -0.001(3) 0.003(3) C50 0.025(4) 0.031(4) 0.015(4) -0.010(3) 0.002(3) -0.007(3) C51 0.022(4) 0.037(4) 0.012(4) -0.003(3) -0.006(3) 0.003(4) C52 0.029(5) 0.029(4) 0.017(4) 0.004(3) 0.000(3) 0.001(3) C53 0.021(4) 0.026(4) 0.015(4) 0.000(3) 0.000(3) -0.003(3) C54 0.018(4) 0.027(3) 0.014(3) -0.001(3) 0.001(3) 0.004(3) C55 0.007(4) 0.025(3) 0.021(4) -0.003(3) -0.009(3) 0.005(3) O56 0.023(3) 0.032(3) 0.016(3) -0.001(2) -0.001(2) 0.005(2) O57 0.036(3) 0.019(2) 0.026(3) -0.002(2) 0.000(2) 0.002(2) C58 0.057(6) 0.026(4) 0.042(5) -0.019(3) -0.008(5) 0.013(4) C59 0.029(5) 0.025(3) 0.021(4) -0.005(3) -0.003(3) 0.003(3) C61 0.012(4) 0.015(3) 0.021(4) 0.002(3) -0.001(3) -0.006(3) C62 0.015(4) 0.017(3) 0.014(3) 0.001(3) 0.001(3) -0.002(3) C63 0.023(4) 0.020(3) 0.013(4) 0.003(3) -0.004(3) 0.000(4) C64 0.012(4) 0.015(3) 0.019(4) 0.007(3) -0.004(3) -0.004(3) C65 0.015(4) 0.008(3) 0.015(3) 0.000(3) -0.002(3) 0.001(3) C66 0.018(4) 0.020(4) 0.013(4) -0.004(3) 0.002(3) 0.001(3) O67 0.013(3) 0.040(3) 0.016(3) -0.001(3) 0.001(3) -0.003(2) C68 0.016(4) 0.020(3) 0.014(3) -0.005(3) -0.001(3) -0.005(3) C69 0.021(4) 0.027(4) 0.020(4) -0.001(3) 0.000(3) 0.001(3) C70 0.022(4) 0.037(4) 0.026(4) -0.011(3) -0.003(3) 0.005(4) C71 0.021(4) 0.043(4) 0.022(4) -0.011(3) 0.006(4) -0.006(4) C72 0.028(5) 0.041(4) 0.015(4) -0.003(3) -0.001(3) -0.008(4) C73 0.022(4) 0.024(4) 0.017(4) -0.001(3) 0.002(3) 0.001(3) C74 0.016(4) 0.017(3) 0.012(3) -0.002(3) 0.002(3) -0.001(3) C75 0.004(4) 0.019(3) 0.019(4) -0.002(3) 0.003(3) -0.004(3) O76 0.027(3) 0.024(2) 0.017(3) -0.002(2) -0.005(2) 0.001(2) O77 0.033(3) 0.015(2) 0.020(2) 0.0020(18) 0.003(2) 0.000(2) C78 0.049(5) 0.016(3) 0.035(4) 0.008(3) 0.009(4) 0.005(4) C79 0.016(4) 0.025(3) 0.018(4) -0.002(3) 0.000(3) 0.003(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O7 1.378(6) . ? C1 C6 1.380(7) . ? C1 C2 1.404(7) . ? C2 C3 1.392(7) . ? C2 C8 1.487(7) . ? C3 C4 1.379(7) . ? C3 H3 0.9500 . ? C4 C5 1.398(7) . ? C4 H4 0.9500 . ? C5 C6 1.393(7) . ? C5 C14 1.514(7) . ? C6 H6 0.9500 . ? O7 H7 0.82(5) . ? C8 C13 1.387(7) . ? C8 C9 1.390(7) . ? C9 C10 1.394(7) . ? C9 H9 0.9500 . ? C10 C11 1.383(7) . ? C10 H10 0.9500 . ? C11 C12 1.373(8) . ? C11 H11 0.9500 . ? C12 C13 1.378(8) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.503(7) . ? C14 C19 1.530(7) . ? C14 H14 1.0000 . ? C15 O16 1.217(6) . ? C15 O17 1.328(6) . ? O17 C18 1.477(7) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C21 O27 1.376(7) . ? C21 C26 1.389(7) . ? C21 C22 1.395(7) . ? C22 C23 1.390(7) . ? C22 C28 1.482(7) . ? C23 C24 1.384(7) . ? C23 H23 0.9500 . ? C24 C25 1.400(7) . ? C24 H24 0.9500 . ? C25 C26 1.390(7) . ? C25 C34 1.514(7) . ? C26 H26 0.9500 . ? O27 H27 0.78(6) . ? C28 C33 1.391(7) . ? C28 C29 1.396(7) . ? C29 C30 1.385(8) . ? C29 H29 0.9500 . ? C30 C31 1.385(7) . ? C30 H30 0.9500 . ? C31 C32 1.376(7) . ? C31 H31 0.9500 . ? C32 C33 1.381(7) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 C35 1.508(7) . ? C34 C39 1.525(7) . ? C34 H34 1.0000 . ? C35 O36 1.218(6) . ? C35 O37 1.332(6) . ? O37 C38 1.449(6) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C41 C46 1.375(7) . ? C41 O47 1.377(7) . ? C41 C42 1.400(7) . ? C42 C43 1.397(7) . ? C42 C48 1.480(7) . ? C43 C44 1.386(7) . ? C43 H43 0.9500 . ? C44 C45 1.388(7) . ? C44 H44 0.9500 . ? C45 C46 1.384(7) . ? C45 C54 1.529(7) . ? C46 H46 0.9500 . ? O47 H47 0.82(6) . ? C48 C49 1.385(7) . ? C48 C53 1.392(7) . ? C49 C50 1.384(7) . ? C49 H49 0.9500 . ? C50 C51 1.381(7) . ? C50 H50 0.9500 . ? C51 C52 1.379(7) . ? C51 H51 0.9500 . ? C52 C53 1.390(7) . ? C52 H52 0.9500 . ? C53 H53 0.9500 . ? C54 C55 1.507(7) . ? C54 C59 1.538(7) . ? C54 H54 1.0000 . ? C55 O56 1.219(6) . ? C55 O57 1.336(6) . ? O57 C58 1.467(6) . ? C58 H58A 0.9800 . ? C58 H58B 0.9800 . ? C58 H58C 0.9800 . ? C59 H59A 0.9800 . ? C59 H59B 0.9800 . ? C59 H59C 0.9800 . ? C61 O67 1.376(7) . ? C61 C66 1.382(7) . ? C61 C62 1.406(7) . ? C62 C63 1.374(7) . ? C62 C68 1.490(7) . ? C63 C64 1.385(7) . ? C63 H63 0.9500 . ? C64 C65 1.395(7) . ? C64 H64 0.9500 . ? C65 C66 1.384(7) . ? C65 C74 1.513(7) . ? C66 H66 0.9500 . ? O67 H67 0.74(6) . ? C68 C69 1.384(7) . ? C68 C73 1.400(7) . ? C69 C70 1.391(7) . ? C69 H69 0.9500 . ? C70 C71 1.382(7) . ? C70 H70 0.9500 . ? C71 C72 1.372(8) . ? C71 H71 0.9500 . ? C72 C73 1.396(7) . ? C72 H72 0.9500 . ? C73 H73 0.9500 . ? C74 C75 1.506(7) . ? C74 C79 1.535(6) . ? C74 H74 1.0000 . ? C75 O76 1.202(6) . ? C75 O77 1.335(6) . ? O77 C78 1.467(6) . ? C78 H78A 0.9800 . ? C78 H78B 0.9800 . ? C78 H78C 0.9800 . ? C79 H79A 0.9800 . ? C79 H79B 0.9800 . ? C79 H79C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 C1 C6 121.4(5) . . ? O7 C1 C2 117.0(5) . . ? C6 C1 C2 121.6(5) . . ? C3 C2 C1 116.7(5) . . ? C3 C2 C8 121.4(5) . . ? C1 C2 C8 121.8(5) . . ? C4 C3 C2 122.1(5) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 120.7(6) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 117.9(5) . . ? C6 C5 C14 121.2(5) . . ? C4 C5 C14 120.9(5) . . ? C1 C6 C5 121.0(5) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C1 O7 H7 112(5) . . ? C13 C8 C9 118.1(5) . . ? C13 C8 C2 119.9(5) . . ? C9 C8 C2 121.9(5) . . ? C8 C9 C10 121.0(5) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C11 C10 C9 119.5(6) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C12 C11 C10 119.9(6) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 120.5(6) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 121.0(6) . . ? C12 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? C15 C14 C5 109.0(5) . . ? C15 C14 C19 110.8(5) . . ? C5 C14 C19 111.3(4) . . ? C15 C14 H14 108.5 . . ? C5 C14 H14 108.5 . . ? C19 C14 H14 108.5 . . ? O16 C15 O17 122.7(5) . . ? O16 C15 C14 125.2(5) . . ? O17 C15 C14 112.0(5) . . ? C15 O17 C18 116.4(5) . . ? O17 C18 H18A 109.5 . . ? O17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O27 C21 C26 120.3(5) . . ? O27 C21 C22 118.5(5) . . ? C26 C21 C22 121.2(5) . . ? C23 C22 C21 116.9(5) . . ? C23 C22 C28 120.1(5) . . ? C21 C22 C28 123.0(5) . . ? C24 C23 C22 122.8(5) . . ? C24 C23 H23 118.6 . . ? C22 C23 H23 118.6 . . ? C23 C24 C25 119.5(6) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C26 C25 C24 118.5(5) . . ? C26 C25 C34 121.0(5) . . ? C24 C25 C34 120.2(5) . . ? C21 C26 C25 121.0(5) . . ? C21 C26 H26 119.5 . . ? C25 C26 H26 119.5 . . ? C21 O27 H27 111(5) . . ? C33 C28 C29 117.0(5) . . ? C33 C28 C22 121.5(5) . . ? C29 C28 C22 121.5(5) . . ? C30 C29 C28 121.7(5) . . ? C30 C29 H29 119.1 . . ? C28 C29 H29 119.1 . . ? C29 C30 C31 119.7(6) . . ? C29 C30 H30 120.2 . . ? C31 C30 H30 120.2 . . ? C32 C31 C30 119.6(6) . . ? C32 C31 H31 120.2 . . ? C30 C31 H31 120.2 . . ? C31 C32 C33 120.3(5) . . ? C31 C32 H32 119.9 . . ? C33 C32 H32 119.9 . . ? C32 C33 C28 121.7(5) . . ? C32 C33 H33 119.2 . . ? C28 C33 H33 119.2 . . ? C35 C34 C25 110.6(5) . . ? C35 C34 C39 110.1(5) . . ? C25 C34 C39 110.9(5) . . ? C35 C34 H34 108.4 . . ? C25 C34 H34 108.4 . . ? C39 C34 H34 108.4 . . ? O36 C35 O37 122.5(5) . . ? O36 C35 C34 125.7(5) . . ? O37 C35 C34 111.8(5) . . ? C35 O37 C38 116.4(4) . . ? O37 C38 H38A 109.5 . . ? O37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C34 C39 H39A 109.5 . . ? C34 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C34 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C46 C41 O47 121.1(5) . . ? C46 C41 C42 121.1(5) . . ? O47 C41 C42 117.9(5) . . ? C43 C42 C41 116.8(5) . . ? C43 C42 C48 121.4(5) . . ? C41 C42 C48 121.7(5) . . ? C44 C43 C42 121.8(5) . . ? C44 C43 H43 119.1 . . ? C42 C43 H43 119.1 . . ? C43 C44 C45 120.5(5) . . ? C43 C44 H44 119.8 . . ? C45 C44 H44 119.8 . . ? C46 C45 C44 118.0(5) . . ? C46 C45 C54 121.5(5) . . ? C44 C45 C54 120.4(5) . . ? C41 C46 C45 121.8(5) . . ? C41 C46 H46 119.1 . . ? C45 C46 H46 119.1 . . ? C41 O47 H47 109(5) . . ? C49 C48 C53 118.6(5) . . ? C49 C48 C42 121.3(5) . . ? C53 C48 C42 120.1(5) . . ? C50 C49 C48 121.0(5) . . ? C50 C49 H49 119.5 . . ? C48 C49 H49 119.5 . . ? C51 C50 C49 119.6(6) . . ? C51 C50 H50 120.2 . . ? C49 C50 H50 120.2 . . ? C52 C51 C50 120.6(6) . . ? C52 C51 H51 119.7 . . ? C50 C51 H51 119.7 . . ? C51 C52 C53 119.3(6) . . ? C51 C52 H52 120.3 . . ? C53 C52 H52 120.3 . . ? C52 C53 C48 120.9(5) . . ? C52 C53 H53 119.6 . . ? C48 C53 H53 119.6 . . ? C55 C54 C45 106.6(5) . . ? C55 C54 C59 111.7(5) . . ? C45 C54 C59 111.8(5) . . ? C55 C54 H54 108.9 . . ? C45 C54 H54 108.9 . . ? C59 C54 H54 108.9 . . ? O56 C55 O57 122.7(5) . . ? O56 C55 C54 125.4(5) . . ? O57 C55 C54 111.9(5) . . ? C55 O57 C58 116.1(5) . . ? O57 C58 H58A 109.5 . . ? O57 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? O57 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C54 C59 H59A 109.5 . . ? C54 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C54 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? O67 C61 C66 121.2(5) . . ? O67 C61 C62 117.5(5) . . ? C66 C61 C62 121.3(5) . . ? C63 C62 C61 116.4(5) . . ? C63 C62 C68 120.6(5) . . ? C61 C62 C68 122.9(5) . . ? C62 C63 C64 123.1(5) . . ? C62 C63 H63 118.4 . . ? C64 C63 H63 118.4 . . ? C63 C64 C65 119.8(5) . . ? C63 C64 H64 120.1 . . ? C65 C64 H64 120.1 . . ? C66 C65 C64 118.2(5) . . ? C66 C65 C74 121.3(5) . . ? C64 C65 C74 120.5(5) . . ? C61 C66 C65 121.2(5) . . ? C61 C66 H66 119.4 . . ? C65 C66 H66 119.4 . . ? C61 O67 H67 113(6) . . ? C69 C68 C73 118.1(5) . . ? C69 C68 C62 122.7(5) . . ? C73 C68 C62 119.1(5) . . ? C68 C69 C70 121.2(6) . . ? C68 C69 H69 119.4 . . ? C70 C69 H69 119.4 . . ? C71 C70 C69 120.2(6) . . ? C71 C70 H70 119.9 . . ? C69 C70 H70 119.9 . . ? C72 C71 C70 119.5(6) . . ? C72 C71 H71 120.3 . . ? C70 C71 H71 120.3 . . ? C71 C72 C73 120.7(6) . . ? C71 C72 H72 119.7 . . ? C73 C72 H72 119.7 . . ? C72 C73 C68 120.3(6) . . ? C72 C73 H73 119.8 . . ? C68 C73 H73 119.8 . . ? C75 C74 C65 110.4(5) . . ? C75 C74 C79 111.2(4) . . ? C65 C74 C79 111.3(5) . . ? C75 C74 H74 107.9 . . ? C65 C74 H74 107.9 . . ? C79 C74 H74 107.9 . . ? O76 C75 O77 123.0(5) . . ? O76 C75 C74 125.5(5) . . ? O77 C75 C74 111.4(5) . . ? C75 O77 C78 115.8(4) . . ? O77 C78 H78A 109.5 . . ? O77 C78 H78B 109.5 . . ? H78A C78 H78B 109.5 . . ? O77 C78 H78C 109.5 . . ? H78A C78 H78C 109.5 . . ? H78B C78 H78C 109.5 . . ? C74 C79 H79A 109.5 . . ? C74 C79 H79B 109.5 . . ? H79A C79 H79B 109.5 . . ? C74 C79 H79C 109.5 . . ? H79A C79 H79C 109.5 . . ? H79B C79 H79C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O7 C1 C2 C3 176.7(5) . . . . ? C6 C1 C2 C3 -2.7(8) . . . . ? O7 C1 C2 C8 -1.9(8) . . . . ? C6 C1 C2 C8 178.7(5) . . . . ? C1 C2 C3 C4 2.0(8) . . . . ? C8 C2 C3 C4 -179.4(5) . . . . ? C2 C3 C4 C5 -0.4(9) . . . . ? C3 C4 C5 C6 -0.4(8) . . . . ? C3 C4 C5 C14 176.5(5) . . . . ? O7 C1 C6 C5 -177.4(5) . . . . ? C2 C1 C6 C5 2.0(8) . . . . ? C4 C5 C6 C1 -0.4(8) . . . . ? C14 C5 C6 C1 -177.2(5) . . . . ? C3 C2 C8 C13 -48.5(8) . . . . ? C1 C2 C8 C13 130.0(6) . . . . ? C3 C2 C8 C9 130.4(6) . . . . ? C1 C2 C8 C9 -51.1(8) . . . . ? C13 C8 C9 C10 -0.1(9) . . . . ? C2 C8 C9 C10 -179.1(5) . . . . ? C8 C9 C10 C11 -0.8(9) . . . . ? C9 C10 C11 C12 0.3(9) . . . . ? C10 C11 C12 C13 1.2(9) . . . . ? C11 C12 C13 C8 -2.2(9) . . . . ? C9 C8 C13 C12 1.6(9) . . . . ? C2 C8 C13 C12 -179.4(5) . . . . ? C6 C5 C14 C15 -37.8(7) . . . . ? C4 C5 C14 C15 145.5(5) . . . . ? C6 C5 C14 C19 84.8(6) . . . . ? C4 C5 C14 C19 -92.0(6) . . . . ? C5 C14 C15 O16 103.0(7) . . . . ? C19 C14 C15 O16 -19.8(9) . . . . ? C5 C14 C15 O17 -74.1(6) . . . . ? C19 C14 C15 O17 163.1(5) . . . . ? O16 C15 O17 C18 -1.3(9) . . . . ? C14 C15 O17 C18 175.9(5) . . . . ? O27 C21 C22 C23 177.4(5) . . . . ? C26 C21 C22 C23 -3.8(8) . . . . ? O27 C21 C22 C28 -2.4(8) . . . . ? C26 C21 C22 C28 176.4(5) . . . . ? C21 C22 C23 C24 2.3(8) . . . . ? C28 C22 C23 C24 -178.0(5) . . . . ? C22 C23 C24 C25 0.5(9) . . . . ? C23 C24 C25 C26 -1.9(8) . . . . ? C23 C24 C25 C34 171.8(5) . . . . ? O27 C21 C26 C25 -178.6(5) . . . . ? C22 C21 C26 C25 2.6(8) . . . . ? C24 C25 C26 C21 0.3(8) . . . . ? C34 C25 C26 C21 -173.3(5) . . . . ? C23 C22 C28 C33 -42.3(8) . . . . ? C21 C22 C28 C33 137.5(6) . . . . ? C23 C22 C28 C29 135.1(6) . . . . ? C21 C22 C28 C29 -45.2(8) . . . . ? C33 C28 C29 C30 0.1(9) . . . . ? C22 C28 C29 C30 -177.4(5) . . . . ? C28 C29 C30 C31 -1.0(9) . . . . ? C29 C30 C31 C32 1.3(9) . . . . ? C30 C31 C32 C33 -0.9(9) . . . . ? C31 C32 C33 C28 0.0(9) . . . . ? C29 C28 C33 C32 0.4(9) . . . . ? C22 C28 C33 C32 177.9(5) . . . . ? C26 C25 C34 C35 -40.5(7) . . . . ? C24 C25 C34 C35 146.0(5) . . . . ? C26 C25 C34 C39 81.9(7) . . . . ? C24 C25 C34 C39 -91.6(6) . . . . ? C25 C34 C35 O36 107.3(7) . . . . ? C39 C34 C35 O36 -15.6(9) . . . . ? C25 C34 C35 O37 -73.0(6) . . . . ? C39 C34 C35 O37 164.1(5) . . . . ? O36 C35 O37 C38 -3.4(9) . . . . ? C34 C35 O37 C38 176.9(5) . . . . ? C46 C41 C42 C43 -1.4(8) . . . . ? O47 C41 C42 C43 177.8(5) . . . . ? C46 C41 C42 C48 -178.8(5) . . . . ? O47 C41 C42 C48 0.4(8) . . . . ? C41 C42 C43 C44 0.7(9) . . . . ? C48 C42 C43 C44 178.1(5) . . . . ? C42 C43 C44 C45 0.0(9) . . . . ? C43 C44 C45 C46 0.1(8) . . . . ? C43 C44 C45 C54 177.0(5) . . . . ? O47 C41 C46 C45 -177.6(6) . . . . ? C42 C41 C46 C45 1.6(9) . . . . ? C44 C45 C46 C41 -0.9(9) . . . . ? C54 C45 C46 C41 -177.7(5) . . . . ? C43 C42 C48 C49 129.3(6) . . . . ? C41 C42 C48 C49 -53.4(8) . . . . ? C43 C42 C48 C53 -51.6(8) . . . . ? C41 C42 C48 C53 125.7(6) . . . . ? C53 C48 C49 C50 0.8(9) . . . . ? C42 C48 C49 C50 180.0(5) . . . . ? C48 C49 C50 C51 -2.4(9) . . . . ? C49 C50 C51 C52 2.0(9) . . . . ? C50 C51 C52 C53 0.1(9) . . . . ? C51 C52 C53 C48 -1.8(9) . . . . ? C49 C48 C53 C52 1.3(9) . . . . ? C42 C48 C53 C52 -177.8(5) . . . . ? C46 C45 C54 C55 -54.4(7) . . . . ? C44 C45 C54 C55 128.8(5) . . . . ? C46 C45 C54 C59 67.9(7) . . . . ? C44 C45 C54 C59 -108.9(6) . . . . ? C45 C54 C55 O56 100.2(7) . . . . ? C59 C54 C55 O56 -22.1(9) . . . . ? C45 C54 C55 O57 -78.2(6) . . . . ? C59 C54 C55 O57 159.5(5) . . . . ? O56 C55 O57 C58 -2.2(9) . . . . ? C54 C55 O57 C58 176.2(5) . . . . ? O67 C61 C62 C63 -178.2(5) . . . . ? C66 C61 C62 C63 0.5(9) . . . . ? O67 C61 C62 C68 2.1(8) . . . . ? C66 C61 C62 C68 -179.1(5) . . . . ? C61 C62 C63 C64 -1.8(9) . . . . ? C68 C62 C63 C64 177.9(5) . . . . ? C62 C63 C64 C65 1.4(9) . . . . ? C63 C64 C65 C66 0.4(8) . . . . ? C63 C64 C65 C74 177.7(5) . . . . ? O67 C61 C66 C65 179.9(5) . . . . ? C62 C61 C66 C65 1.2(9) . . . . ? C64 C65 C66 C61 -1.7(8) . . . . ? C74 C65 C66 C61 -178.9(5) . . . . ? C63 C62 C68 C69 -130.5(7) . . . . ? C61 C62 C68 C69 49.2(8) . . . . ? C63 C62 C68 C73 45.8(8) . . . . ? C61 C62 C68 C73 -134.5(6) . . . . ? C73 C68 C69 C70 -0.1(9) . . . . ? C62 C68 C69 C70 176.2(5) . . . . ? C68 C69 C70 C71 1.4(9) . . . . ? C69 C70 C71 C72 -1.3(9) . . . . ? C70 C71 C72 C73 -0.1(9) . . . . ? C71 C72 C73 C68 1.4(9) . . . . ? C69 C68 C73 C72 -1.3(9) . . . . ? C62 C68 C73 C72 -177.7(5) . . . . ? C66 C65 C74 C75 -43.6(7) . . . . ? C64 C65 C74 C75 139.2(5) . . . . ? C66 C65 C74 C79 80.5(7) . . . . ? C64 C65 C74 C79 -96.7(6) . . . . ? C65 C74 C75 O76 109.5(7) . . . . ? C79 C74 C75 O76 -14.7(9) . . . . ? C65 C74 C75 O77 -70.1(6) . . . . ? C79 C74 C75 O77 165.8(5) . . . . ? O76 C75 O77 C78 -2.2(9) . . . . ? C74 C75 O77 C78 177.4(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H7 O56 0.82(5) 1.95(5) 2.768(5) 172(6) . O27 H27 O76 0.78(6) 2.05(6) 2.830(6) 180(8) . O47 H47 O16 0.82(6) 1.98(6) 2.791(6) 169(6) . O67 H67 O36 0.74(6) 2.13(6) 2.832(6) 161(7) . # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF data_uv03cja1n _database_code_depnum_ccdc_archive 'CCDC 910284' #TrackingRef '15322_web_deposit_cif_file_0_IgnacioVaya_1352455375.ccdc_deposit.cif' _audit_creation_date 2010-11-09T10:51:30-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common S-FBPOH/R-Trp _chemical_formula_moiety 'C27 H26 N2 O4' _chemical_formula_sum 'C27 H26 N2 O4' _chemical_formula_weight 442.5 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 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' _cell_length_a 10.6549(4) _cell_length_b 12.0512(5) _cell_length_c 17.2822(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2219.11(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3379 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 28.28 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.37 _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8610 _exptl_absorpt_correction_T_max 0.9708 _exptl_absorpt_process_details 'BRUKER AXS - SADABS' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Bruker X8 kappa APEXII CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_unetI/netI 0.0413 _diffrn_reflns_number 19302 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.29 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 3096 _reflns_number_gt 2684 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 v2010.9-1 (Bruker AXS, 2010)' _computing_cell_refinement 'APEX2 v2010.9-1 (Bruker AXS, 2010)' _computing_data_reduction 'APEX2 v2010.9-1 (Bruker AXS, 2010)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(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^)+(0.0290P)^2^+1.6434P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3096 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.0996 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.275 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.058 #----------------------------------------------------------------------------# # 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 C1 C 0.3184(3) 0.3191(2) 0.16235(16) 0.0165(6) Uani 1 1 d . . . C2 C 0.3565(3) 0.3541(2) 0.23627(16) 0.0154(6) Uani 1 1 d . . . C3 C 0.4591(3) 0.4261(3) 0.24025(16) 0.0184(6) Uani 1 1 d . . . H3 H 0.4884 0.449 0.2896 0.022 Uiso 1 1 calc R . . C4 C 0.5194(3) 0.4650(3) 0.17506(16) 0.0188(6) Uani 1 1 d . . . H4 H 0.5885 0.5144 0.18 0.023 Uiso 1 1 calc R . . C5 C 0.4789(3) 0.4321(2) 0.10185(16) 0.0146(6) Uani 1 1 d . . . C6 C 0.3788(3) 0.3584(2) 0.09656(16) 0.0160(6) Uani 1 1 d . . . H6 H 0.3512 0.3345 0.047 0.019 Uiso 1 1 calc R . . O7 O 0.2210(2) 0.24589(18) 0.15683(12) 0.0234(5) Uani 1 1 d . . . H7 H 0.211(4) 0.229(3) 0.112(2) 0.028 Uiso 1 1 d . . . C8 C 0.2900(3) 0.3190(2) 0.30799(16) 0.0158(6) Uani 1 1 d . . . C9 C 0.1591(3) 0.3148(2) 0.31055(16) 0.0176(6) Uani 1 1 d . . . H9 H 0.1121 0.3343 0.2658 0.021 Uiso 1 1 calc R . . C10 C 0.0962(3) 0.2827(3) 0.37744(16) 0.0191(6) Uani 1 1 d . . . H10 H 0.0072 0.2782 0.3777 0.023 Uiso 1 1 calc R . . C11 C 0.1633(3) 0.2574(3) 0.44346(17) 0.0222(7) Uani 1 1 d . . . H11 H 0.1206 0.236 0.4893 0.027 Uiso 1 1 calc R . . C12 C 0.2935(3) 0.2634(3) 0.44270(18) 0.0234(7) Uani 1 1 d . . . H12 H 0.3398 0.2473 0.4883 0.028 Uiso 1 1 calc R . . C13 C 0.3559(3) 0.2928(3) 0.37508(17) 0.0206(6) Uani 1 1 d . . . H13 H 0.445 0.2951 0.3747 0.025 Uiso 1 1 calc R . . C14 C 0.5438(3) 0.4778(2) 0.02913(16) 0.0161(6) Uani 1 1 d . . . H14 H 0.5574 0.5592 0.0368 0.019 Uiso 1 1 calc R . . C15 C 0.6720(3) 0.4229(2) 0.02090(15) 0.0148(6) Uani 1 1 d . . . O16 O 0.6856(2) 0.33473(17) -0.01422(11) 0.0212(5) Uani 1 1 d . . . N17 N 0.7691(2) 0.4720(2) 0.05588(13) 0.0144(5) Uani 1 1 d . . . H17 H 0.756(3) 0.531(3) 0.0815(17) 0.017 Uiso 1 1 d . . . C18 C 0.8920(3) 0.4210(2) 0.05724(15) 0.0150(6) Uani 1 1 d . . . H18 H 0.8793 0.3393 0.064 0.018 Uiso 1 1 calc R . . C19 C 0.4691(3) 0.4620(3) -0.04536(16) 0.0230(7) Uani 1 1 d . . . H19A H 0.459 0.3826 -0.0557 0.034 Uiso 1 1 calc R . . H19B H 0.514 0.4969 -0.0885 0.034 Uiso 1 1 calc R . . H19C H 0.3863 0.4965 -0.0397 0.034 Uiso 1 1 calc R . . C20 C 0.9580(3) 0.4381(2) -0.02006(16) 0.0164(6) Uani 1 1 d . . . O21 O 0.9198(2) 0.49399(19) -0.07262(11) 0.0245(5) Uani 1 1 d . . . O22 O 1.0631(2) 0.37905(19) -0.02229(12) 0.0261(5) Uani 1 1 d . . . C23 C 1.1293(3) 0.3776(3) -0.09540(18) 0.0276(8) Uani 1 1 d . . . H23A H 1.1589 0.4526 -0.1076 0.041 Uiso 1 1 calc R . . H23B H 1.0725 0.3521 -0.1363 0.041 Uiso 1 1 calc R . . H23C H 1.2012 0.3271 -0.0918 0.041 Uiso 1 1 calc R . . C24 C 0.9690(3) 0.4625(3) 0.12718(15) 0.0173(6) Uani 1 1 d . . . H24A H 1.0497 0.4218 0.1297 0.021 Uiso 1 1 calc R . . H24B H 0.9878 0.5424 0.1208 0.021 Uiso 1 1 calc R . . C25 C 0.8972(3) 0.4448(2) 0.20094(15) 0.0154(6) Uani 1 1 d . . . C26 C 0.8465(3) 0.5252(3) 0.24673(16) 0.0191(6) Uani 1 1 d . . . H26 H 0.8567 0.6027 0.239 0.023 Uiso 1 1 calc R . . N27 N 0.7788(3) 0.4779(2) 0.30554(14) 0.0211(6) Uani 1 1 d . . . H27 H 0.738(3) 0.514(3) 0.3398(19) 0.025 Uiso 1 1 d . . . C28 C 0.7835(3) 0.3646(3) 0.29821(16) 0.0187(6) Uani 1 1 d . . . C29 C 0.7298(3) 0.2819(3) 0.34363(18) 0.0244(7) Uani 1 1 d . . . H29 H 0.6796 0.3 0.3873 0.029 Uiso 1 1 calc R . . C30 C 0.7518(3) 0.1729(3) 0.32320(19) 0.0286(8) Uani 1 1 d . . . H30 H 0.7152 0.1149 0.3529 0.034 Uiso 1 1 calc R . . C31 C 0.8273(3) 0.1465(3) 0.25924(18) 0.0256(7) Uani 1 1 d . . . H31 H 0.8416 0.0709 0.2466 0.031 Uiso 1 1 calc R . . C32 C 0.8813(3) 0.2285(2) 0.21430(16) 0.0182(6) Uani 1 1 d . . . H32 H 0.9331 0.2096 0.1715 0.022 Uiso 1 1 calc R . . C33 C 0.8583(3) 0.3403(2) 0.23287(15) 0.0147(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0159(14) 0.0168(14) 0.0167(14) -0.0015(11) -0.0006(12) -0.0006(12) C2 0.0146(14) 0.0188(14) 0.0128(13) -0.0018(11) 0.0000(11) 0.0026(12) C3 0.0146(14) 0.0278(15) 0.0128(13) -0.0052(12) -0.0031(12) -0.0011(13) C4 0.0121(14) 0.0244(15) 0.0200(14) -0.0056(12) -0.0002(12) -0.0041(12) C5 0.0127(13) 0.0181(14) 0.0131(13) -0.0017(11) 0.0007(12) 0.0017(12) C6 0.0155(14) 0.0211(14) 0.0116(13) -0.0015(11) -0.0018(12) 0.0002(12) O7 0.0300(12) 0.0287(12) 0.0116(9) -0.0029(9) 0.0012(10) -0.0148(11) C8 0.0179(14) 0.0171(14) 0.0124(13) -0.0030(11) 0.0016(11) -0.0001(12) C9 0.0185(15) 0.0202(14) 0.0142(14) -0.0029(12) -0.0039(12) 0.0010(12) C10 0.0174(15) 0.0233(15) 0.0167(15) -0.0012(12) 0.0005(12) 0.0001(13) C11 0.0272(17) 0.0247(16) 0.0146(15) 0.0024(13) 0.0072(14) -0.0002(14) C12 0.0266(18) 0.0281(17) 0.0154(15) 0.0003(13) -0.0045(13) 0.0050(14) C13 0.0169(15) 0.0265(16) 0.0183(15) -0.0001(13) -0.0019(13) 0.0020(13) C14 0.0140(14) 0.0184(14) 0.0160(13) -0.0002(11) -0.0004(11) -0.0020(12) C15 0.0167(14) 0.0183(13) 0.0094(12) 0.0034(11) 0.0031(11) -0.0008(12) O16 0.0240(11) 0.0224(11) 0.0173(10) -0.0069(9) 0.0036(9) -0.0004(10) N17 0.0134(11) 0.0174(12) 0.0125(11) -0.0040(10) 0.0026(10) 0.0020(10) C18 0.0156(14) 0.0176(13) 0.0119(13) 0.0028(11) 0.0022(12) 0.0016(12) C19 0.0204(16) 0.0358(18) 0.0127(14) 0.0078(13) -0.0028(12) -0.0056(15) C20 0.0158(14) 0.0189(14) 0.0144(13) -0.0014(12) -0.0006(12) -0.0002(12) O21 0.0191(11) 0.0373(13) 0.0171(10) 0.0123(10) -0.0005(9) 0.0039(10) O22 0.0255(12) 0.0361(13) 0.0168(11) 0.0092(10) 0.0091(10) 0.0152(10) C23 0.0251(17) 0.0379(19) 0.0199(15) 0.0042(14) 0.0081(15) 0.0096(15) C24 0.0155(15) 0.0202(15) 0.0164(14) 0.0014(12) -0.0013(12) 0.0003(12) C25 0.0148(14) 0.0209(14) 0.0104(13) -0.0002(11) -0.0029(11) 0.0003(12) C26 0.0182(15) 0.0223(14) 0.0167(14) -0.0005(12) -0.0033(12) 0.0008(13) N27 0.0191(13) 0.0307(14) 0.0134(12) -0.0049(11) 0.0014(11) 0.0037(12) C28 0.0133(14) 0.0289(16) 0.0140(13) 0.0004(12) -0.0050(12) 0.0023(13) C29 0.0142(14) 0.0437(19) 0.0153(14) 0.0084(14) -0.0011(12) -0.0008(15) C30 0.0229(18) 0.0369(19) 0.0259(16) 0.0153(15) -0.0069(14) -0.0104(15) C31 0.0253(17) 0.0238(16) 0.0278(17) 0.0044(14) -0.0104(15) -0.0039(14) C32 0.0199(15) 0.0238(15) 0.0110(13) 0.0008(11) -0.0039(12) 0.0007(13) C33 0.0111(13) 0.0244(15) 0.0086(12) 0.0000(11) -0.0021(10) 0.0003(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O7 1.366(4) . ? C1 C6 1.389(4) . ? C1 C2 1.405(4) . ? C2 C3 1.397(4) . ? C2 C8 1.490(4) . ? C3 C4 1.379(4) . ? C3 H3 0.95 . ? C4 C5 1.394(4) . ? C4 H4 0.95 . ? C5 C6 1.391(4) . ? C5 C14 1.537(4) . ? C6 H6 0.95 . ? O7 H7 0.80(4) . ? C8 C13 1.392(4) . ? C8 C9 1.396(4) . ? C9 C10 1.391(4) . ? C9 H9 0.95 . ? C10 C11 1.381(4) . ? C10 H10 0.95 . ? C11 C12 1.388(4) . ? C11 H11 0.95 . ? C12 C13 1.391(4) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 C15 1.524(4) . ? C14 C19 1.525(4) . ? C14 H14 1 . ? C15 O16 1.232(3) . ? C15 N17 1.337(4) . ? N17 C18 1.447(4) . ? N17 H17 0.85(3) . ? C18 C20 1.524(4) . ? C18 C24 1.544(4) . ? C18 H18 1 . ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C19 H19C 0.98 . ? C20 O21 1.202(3) . ? C20 O22 1.327(3) . ? O22 C23 1.447(4) . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? C24 C25 1.502(4) . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? C25 C26 1.362(4) . ? C25 C33 1.436(4) . ? C26 N27 1.370(4) . ? C26 H26 0.95 . ? N27 C28 1.373(4) . ? N27 H27 0.85(4) . ? C28 C29 1.392(4) . ? C28 C33 1.413(4) . ? C29 C30 1.381(5) . ? C29 H29 0.95 . ? C30 C31 1.404(5) . ? C30 H30 0.95 . ? C31 C32 1.382(4) . ? C31 H31 0.95 . ? C32 C33 1.407(4) . ? C32 H32 0.95 . ? 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 O7 C1 C6 121.0(3) . . ? O7 C1 C2 118.5(2) . . ? C6 C1 C2 120.5(3) . . ? C3 C2 C1 117.2(3) . . ? C3 C2 C8 120.5(2) . . ? C1 C2 C8 122.2(3) . . ? C4 C3 C2 122.4(3) . . ? C4 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? C3 C4 C5 120.0(3) . . ? C3 C4 H4 120 . . ? C5 C4 H4 120 . . ? C6 C5 C4 118.6(3) . . ? C6 C5 C14 121.4(2) . . ? C4 C5 C14 120.1(3) . . ? C1 C6 C5 121.3(3) . . ? C1 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C1 O7 H7 109(3) . . ? C13 C8 C9 118.0(3) . . ? C13 C8 C2 121.2(3) . . ? C9 C8 C2 120.8(3) . . ? C10 C9 C8 121.2(3) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C11 C10 C9 119.9(3) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 119.9(3) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C11 C12 C13 119.9(3) . . ? C11 C12 H12 120 . . ? C13 C12 H12 120 . . ? C12 C13 C8 121.1(3) . . ? C12 C13 H13 119.4 . . ? C8 C13 H13 119.4 . . ? C15 C14 C19 109.5(2) . . ? C15 C14 C5 108.9(2) . . ? C19 C14 C5 114.2(2) . . ? C15 C14 H14 108 . . ? C19 C14 H14 108 . . ? C5 C14 H14 108 . . ? O16 C15 N17 120.9(3) . . ? O16 C15 C14 121.8(3) . . ? N17 C15 C14 117.3(2) . . ? C15 N17 C18 121.3(2) . . ? C15 N17 H17 119(2) . . ? C18 N17 H17 119(2) . . ? N17 C18 C20 110.3(2) . . ? N17 C18 C24 110.9(2) . . ? C20 C18 C24 113.4(2) . . ? N17 C18 H18 107.4 . . ? C20 C18 H18 107.4 . . ? C24 C18 H18 107.4 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O21 C20 O22 124.4(3) . . ? O21 C20 C18 125.6(3) . . ? O22 C20 C18 110.0(2) . . ? C20 O22 C23 116.3(2) . . ? O22 C23 H23A 109.5 . . ? O22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C18 110.3(2) . . ? C25 C24 H24A 109.6 . . ? C18 C24 H24A 109.6 . . ? C25 C24 H24B 109.6 . . ? C18 C24 H24B 109.6 . . ? H24A C24 H24B 108.1 . . ? C26 C25 C33 106.6(2) . . ? C26 C25 C24 126.5(3) . . ? C33 C25 C24 126.7(3) . . ? C25 C26 N27 110.2(3) . . ? C25 C26 H26 124.9 . . ? N27 C26 H26 124.9 . . ? C26 N27 C28 109.0(3) . . ? C26 N27 H27 125(2) . . ? C28 N27 H27 126(2) . . ? N27 C28 C29 130.2(3) . . ? N27 C28 C33 107.5(3) . . ? C29 C28 C33 122.3(3) . . ? C30 C29 C28 117.9(3) . . ? C30 C29 H29 121.1 . . ? C28 C29 H29 121.1 . . ? C29 C30 C31 120.9(3) . . ? C29 C30 H30 119.5 . . ? C31 C30 H30 119.5 . . ? C32 C31 C30 121.3(3) . . ? C32 C31 H31 119.4 . . ? C30 C31 H31 119.4 . . ? C31 C32 C33 119.0(3) . . ? C31 C32 H32 120.5 . . ? C33 C32 H32 120.5 . . ? C32 C33 C28 118.6(3) . . ? C32 C33 C25 134.6(3) . . ? C28 C33 C25 106.7(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O7 C1 C2 C3 177.9(3) . . . . ? C6 C1 C2 C3 -2.1(4) . . . . ? O7 C1 C2 C8 -3.5(4) . . . . ? C6 C1 C2 C8 176.6(3) . . . . ? C1 C2 C3 C4 2.0(4) . . . . ? C8 C2 C3 C4 -176.6(3) . . . . ? C2 C3 C4 C5 -0.5(5) . . . . ? C3 C4 C5 C6 -1.0(4) . . . . ? C3 C4 C5 C14 178.4(3) . . . . ? O7 C1 C6 C5 -179.3(3) . . . . ? C2 C1 C6 C5 0.6(4) . . . . ? C4 C5 C6 C1 0.9(4) . . . . ? C14 C5 C6 C1 -178.5(3) . . . . ? C3 C2 C8 C13 -40.8(4) . . . . ? C1 C2 C8 C13 140.6(3) . . . . ? C3 C2 C8 C9 137.1(3) . . . . ? C1 C2 C8 C9 -41.5(4) . . . . ? C13 C8 C9 C10 -1.7(5) . . . . ? C2 C8 C9 C10 -179.6(3) . . . . ? C8 C9 C10 C11 1.9(5) . . . . ? C9 C10 C11 C12 -0.4(5) . . . . ? C10 C11 C12 C13 -1.2(5) . . . . ? C11 C12 C13 C8 1.4(5) . . . . ? C9 C8 C13 C12 0.0(5) . . . . ? C2 C8 C13 C12 178.0(3) . . . . ? C6 C5 C14 C15 -106.9(3) . . . . ? C4 C5 C14 C15 73.6(3) . . . . ? C6 C5 C14 C19 15.9(4) . . . . ? C4 C5 C14 C19 -163.6(3) . . . . ? C19 C14 C15 O16 -37.3(4) . . . . ? C5 C14 C15 O16 88.3(3) . . . . ? C19 C14 C15 N17 145.2(3) . . . . ? C5 C14 C15 N17 -89.3(3) . . . . ? O16 C15 N17 C18 -3.2(4) . . . . ? C14 C15 N17 C18 174.4(2) . . . . ? C15 N17 C18 C20 78.6(3) . . . . ? C15 N17 C18 C24 -155.0(2) . . . . ? N17 C18 C20 O21 6.2(4) . . . . ? C24 C18 C20 O21 -118.8(3) . . . . ? N17 C18 C20 O22 -171.8(2) . . . . ? C24 C18 C20 O22 63.3(3) . . . . ? O21 C20 O22 C23 -4.4(4) . . . . ? C18 C20 O22 C23 173.6(3) . . . . ? N17 C18 C24 C25 54.3(3) . . . . ? C20 C18 C24 C25 179.0(2) . . . . ? C18 C24 C25 C26 -110.8(3) . . . . ? C18 C24 C25 C33 62.7(4) . . . . ? C33 C25 C26 N27 0.3(3) . . . . ? C24 C25 C26 N27 174.9(3) . . . . ? C25 C26 N27 C28 -0.6(4) . . . . ? C26 N27 C28 C29 180.0(3) . . . . ? C26 N27 C28 C33 0.7(3) . . . . ? N27 C28 C29 C30 -179.0(3) . . . . ? C33 C28 C29 C30 0.2(5) . . . . ? C28 C29 C30 C31 0.8(5) . . . . ? C29 C30 C31 C32 -0.5(5) . . . . ? C30 C31 C32 C33 -0.8(5) . . . . ? C31 C32 C33 C28 1.7(4) . . . . ? C31 C32 C33 C25 179.6(3) . . . . ? N27 C28 C33 C32 177.9(3) . . . . ? C29 C28 C33 C32 -1.5(4) . . . . ? N27 C28 C33 C25 -0.5(3) . . . . ? C29 C28 C33 C25 -179.9(3) . . . . ? C26 C25 C33 C32 -177.9(3) . . . . ? C24 C25 C33 C32 7.5(5) . . . . ? C26 C25 C33 C28 0.2(3) . . . . ? C24 C25 C33 C28 -174.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H7 O16 0.80(4) 1.88(4) 2.676(3) 170(4) 3_455 N27 H27 O21 0.85(4) 2.26(4) 3.004(3) 146(3) 2_665 # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF