data_dbred _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H29 N3 O5, 0.5(C6 H14)' _chemical_formula_sum 'C37 H36 N3 O5' _chemical_formula_weight 602.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 32.158(9) _cell_length_b 8.977(3) _cell_length_c 11.478(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3313.7(16) _cell_formula_units_Z 4 _cell_measurement_temperature 108(2) _cell_measurement_reflns_used 2315 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 15.86 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1276 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9731 _exptl_absorpt_correction_T_max 0.9984 _exptl_absorpt_process_details ; Blessing, R. Acta Cryst. (1995) A51 33-38. Sheldrick, G. SADABS (Version 2.10) Bruker/Siemens area detector absorption and other corrections, University of Gottingen, Germany 2003. ; _exptl_special_details ; 2513 frames x 90 sec. @ 4.969 cm; 0.5 deg. steps in omega & phi ; _diffrn_ambient_temperature 108(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20438 _diffrn_reflns_av_R_equivalents 0.1692 _diffrn_reflns_av_sigmaI/netI 0.0579 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 16.55 _reflns_number_total 1081 _reflns_number_gt 912 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART-1K' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; The equivalent of one-half hexane lattice solvate per molecule was modeled by the SQUEEZE subroutine of the PLATON program suite. Two solvent accessible cavities, each located at inversion centers were calculated to have a total volume of 772.6 A^3 and a contribution of 102 e- per lattice due to diffuse solvent scattering. This has ben included in all derived crystal quantities. - PLATON Reference : Spek, A.L. (1990), Acta Cryst. A46, C-34 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^)+(0.1476P)^2^+7.9767P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.020(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absoulte_configuration syn _refine_ls_abs_structure_Flack -4(10) _refine_ls_number_reflns 1081 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1054 _refine_ls_R_factor_gt 0.0928 _refine_ls_wR_factor_ref 0.2744 _refine_ls_wR_factor_gt 0.2662 _refine_ls_goodness_of_fit_ref 1.339 _refine_ls_restrained_S_all 1.339 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.002 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 0.2927(4) 1.1679(14) 0.9422(10) 0.035(4) Uani 1 1 d . . . H1A H 0.2767 1.2419 0.9407 0.052 Uiso 1 1 calc R . . O2 O 0.2470(4) 0.9309(15) 1.0343(10) 0.041(4) Uani 1 1 d . . . H2A H 0.2655 0.8652 1.0295 0.061 Uiso 1 1 calc R . . O3 O 0.3521(4) 1.1426(15) 0.5336(12) 0.048(4) Uani 1 1 d . . . O4 O 0.2104(4) 1.2451(17) 0.7486(12) 0.055(5) Uani 1 1 d . . . O5 O 0.2177(4) 1.3386(16) 0.5253(12) 0.052(5) Uani 1 1 d . . . N1 N 0.3824(5) 0.855(2) 0.9190(14) 0.041(5) Uani 1 1 d . . . N2 N 0.3359(4) 0.9975(17) 0.7441(12) 0.025(5) Uani 1 1 d . . . N3 N 0.2857(5) 0.677(2) 0.8193(14) 0.040(5) Uani 1 1 d . . . C1 C 0.4089(6) 0.787(2) 1.0170(17) 0.030(6) Uiso 1 1 d . . . C2 C 0.3918(6) 0.636(2) 1.0462(18) 0.031(6) Uiso 1 1 d . . . C3 C 0.3947(6) 0.575(2) 1.1572(19) 0.036(6) Uiso 1 1 d . . . H3A H 0.4063 0.6333 1.2183 0.043 Uiso 1 1 calc R . . C4 C 0.3809(5) 0.433(2) 1.1806(19) 0.034(6) Uiso 1 1 d . . . H4A H 0.3822 0.3933 1.2573 0.041 Uiso 1 1 calc R . . C5 C 0.3650(6) 0.348(2) 1.0886(18) 0.040(6) Uiso 1 1 d . . . H5A H 0.3570 0.2477 1.1013 0.048 Uiso 1 1 calc R . . C6 C 0.3609(6) 0.410(3) 0.981(2) 0.044(7) Uiso 1 1 d . . . H6A H 0.3480 0.3537 0.9206 0.053 Uiso 1 1 calc R . . C7 C 0.3750(6) 0.552(2) 0.956(2) 0.047(7) Uiso 1 1 d . . . H7A H 0.3733 0.5917 0.8794 0.056 Uiso 1 1 calc R . . C8 C 0.4523(6) 0.762(2) 0.9688(18) 0.032(6) Uiso 1 1 d . . . C9 C 0.4623(7) 0.778(2) 0.851(2) 0.052(7) Uiso 1 1 d . . . H9A H 0.4412 0.8093 0.7980 0.062 Uiso 1 1 calc R . . C10 C 0.5010(8) 0.751(3) 0.8085(19) 0.059(7) Uiso 1 1 d . . . H10A H 0.5070 0.7684 0.7287 0.071 Uiso 1 1 calc R . . C11 C 0.5317(7) 0.697(2) 0.8821(19) 0.048(7) Uiso 1 1 d . . . H11A H 0.5588 0.6763 0.8533 0.058 Uiso 1 1 calc R . . C12 C 0.5224(6) 0.675(2) 0.9958(18) 0.042(7) Uiso 1 1 d . . . H12A H 0.5428 0.6328 1.0457 0.050 Uiso 1 1 calc R . . C13 C 0.4833(6) 0.712(2) 1.0416(19) 0.039(6) Uiso 1 1 d . . . H13A H 0.4783 0.7034 1.1229 0.047 Uiso 1 1 calc R . . C14 C 0.4102(6) 0.898(2) 1.1262(17) 0.033(6) Uiso 1 1 d . . . C15 C 0.3764(7) 0.900(3) 1.2017(19) 0.045(7) Uiso 1 1 d . . . H15A H 0.3532 0.8370 1.1879 0.054 Uiso 1 1 calc R . . C16 C 0.3765(7) 0.993(2) 1.2955(18) 0.044(6) Uiso 1 1 d . . . H16A H 0.3543 0.9905 1.3502 0.053 Uiso 1 1 calc R . . C17 C 0.4087(6) 1.089(2) 1.3098(19) 0.045(7) Uiso 1 1 d . . . H17A H 0.4091 1.1555 1.3742 0.054 Uiso 1 1 calc R . . C18 C 0.4410(7) 1.089(3) 1.2290(19) 0.051(7) Uiso 1 1 d . . . H18A H 0.4629 1.1595 1.2385 0.061 Uiso 1 1 calc R . . C19 C 0.4428(6) 0.994(2) 1.1378(16) 0.030(6) Uiso 1 1 d . . . H19A H 0.4654 0.9947 1.0846 0.036 Uiso 1 1 calc R . . C20 C 0.3861(6) 1.006(3) 0.8919(17) 0.035(6) Uiso 1 1 d . . . H20A H 0.4051 1.0689 0.9399 0.042 Uiso 1 1 calc R . . C21 C 0.3786(6) 1.048(2) 0.7696(17) 0.038(6) Uiso 1 1 d . . . H21A H 0.3811 1.1570 0.7595 0.046 Uiso 1 1 calc R . . H21B H 0.3989 0.9981 0.7175 0.046 Uiso 1 1 calc R . . C22 C 0.3133(6) 0.939(2) 0.8530(18) 0.029(6) Uiso 1 1 d . . . C23 C 0.3473(6) 0.954(2) 0.9434(19) 0.041(7) Uiso 1 1 d . . . H23A H 0.3402 0.9812 1.0256 0.049 Uiso 1 1 calc R . . C24 C 0.2991(7) 0.792(3) 0.8335(18) 0.030(7) Uiso 1 1 d . . . C25 C 0.2763(6) 1.053(2) 0.8709(16) 0.025(6) Uiso 1 1 d . . . C26 C 0.2719(6) 1.115(2) 0.7416(15) 0.021(6) Uiso 1 1 d . . . C27 C 0.3074(6) 1.086(2) 0.6908(18) 0.033(6) Uiso 1 1 d . . . C28 C 0.2419(7) 1.205(2) 0.6919(19) 0.029(6) Uiso 1 1 d . . . C29 C 0.2499(8) 1.254(3) 0.577(2) 0.051(7) Uiso 1 1 d . . . C30 C 0.2836(7) 1.239(2) 0.5169(18) 0.036(6) Uiso 1 1 d . . . C31 C 0.3175(8) 1.156(2) 0.577(2) 0.041(7) Uiso 1 1 d . . . C32 C 0.2381(5) 0.987(2) 0.9222(16) 0.026(6) Uiso 1 1 d . . . H32A H 0.2160 1.0635 0.9274 0.031 Uiso 1 1 calc R . . H32B H 0.2279 0.9054 0.8716 0.031 Uiso 1 1 calc R . . C33 C 0.1821(7) 1.259(3) 0.500(2) 0.060(8) Uiso 1 1 d . . . H33A H 0.1887 1.1802 0.4439 0.091 Uiso 1 1 calc R . . H33B H 0.1612 1.3260 0.4667 0.091 Uiso 1 1 calc R . . H33C H 0.1712 1.2142 0.5716 0.091 Uiso 1 1 calc R . . C34 C 0.2930(6) 1.303(2) 0.3967(18) 0.051(7) Uiso 1 1 d . . . H34A H 0.2704 1.3699 0.3734 0.077 Uiso 1 1 calc R . . H34B H 0.2954 1.2216 0.3401 0.077 Uiso 1 1 calc R . . H34C H 0.3192 1.3584 0.3995 0.077 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 O1 0.041(8) 0.034(9) 0.030(9) -0.016(8) -0.004(7) 0.009(8) O2 0.032(8) 0.056(11) 0.035(10) 0.006(9) -0.001(7) 0.008(8) O3 0.044(10) 0.051(10) 0.047(9) -0.004(8) 0.015(9) 0.012(8) O4 0.036(10) 0.082(12) 0.046(10) 0.001(10) -0.004(9) 0.006(10) O5 0.046(10) 0.057(11) 0.052(10) -0.003(9) 0.009(9) -0.008(9) N1 0.023(11) 0.067(15) 0.034(12) 0.017(12) -0.002(9) 0.003(10) N2 0.018(10) 0.029(10) 0.027(11) 0.007(10) 0.007(8) -0.001(9) N3 0.036(12) 0.037(14) 0.046(13) 0.003(11) -0.005(10) -0.015(11) _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 C25 1.42(2) . ? O2 C32 1.41(2) . ? O3 C31 1.23(2) . ? O4 C28 1.26(2) . ? O5 C33 1.38(2) . ? O5 C29 1.42(3) . ? N1 C20 1.40(3) . ? N1 C23 1.47(2) . ? N1 C1 1.54(2) . ? N2 C27 1.35(2) . ? N2 C21 1.48(2) . ? N2 C22 1.54(2) . ? N3 C24 1.13(2) . ? C1 C2 1.50(3) . ? C1 C8 1.52(3) . ? C1 C14 1.60(3) . ? C2 C7 1.39(3) . ? C2 C3 1.39(3) . ? C3 C4 1.38(2) . ? C4 C5 1.40(3) . ? C5 C6 1.36(3) . ? C6 C7 1.39(3) . ? C8 C9 1.40(3) . ? C8 C13 1.38(2) . ? C9 C10 1.36(3) . ? C10 C11 1.39(3) . ? C11 C12 1.35(3) . ? C12 C13 1.40(2) . ? C14 C19 1.37(2) . ? C14 C15 1.39(3) . ? C15 C16 1.36(3) . ? C16 C17 1.36(3) . ? C17 C18 1.39(3) . ? C18 C19 1.35(2) . ? C20 C23 1.45(3) . ? C20 C21 1.47(3) . ? C22 C24 1.41(3) . ? C22 C23 1.51(3) . ? C22 C25 1.59(3) . ? C25 C32 1.49(2) . ? C25 C26 1.59(3) . ? C26 C27 1.31(2) . ? C26 C28 1.38(2) . ? C27 C31 1.48(3) . ? C28 C29 1.41(3) . ? C29 C30 1.29(3) . ? C30 C31 1.49(3) . ? C30 C34 1.53(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C33 O5 C29 114.7(17) . . ? C20 N1 C23 61.0(12) . . ? C20 N1 C1 120.2(17) . . ? C23 N1 C1 121.9(15) . . ? C27 N2 C21 122.7(15) . . ? C27 N2 C22 104.4(15) . . ? C21 N2 C22 112.4(14) . . ? C2 C1 C8 106.9(15) . . ? C2 C1 N1 108.6(15) . . ? C8 C1 N1 107.5(15) . . ? C2 C1 C14 113.3(16) . . ? C8 C1 C14 110.6(15) . . ? N1 C1 C14 109.8(14) . . ? C7 C2 C3 119.9(19) . . ? C7 C2 C1 117.7(18) . . ? C3 C2 C1 122.2(19) . . ? C4 C3 C2 121(2) . . ? C3 C4 C5 118(2) . . ? C6 C5 C4 120(2) . . ? C5 C6 C7 122(2) . . ? C2 C7 C6 118(2) . . ? C9 C8 C13 117.1(19) . . ? C9 C8 C1 123.2(18) . . ? C13 C8 C1 119.5(17) . . ? C10 C9 C8 122(2) . . ? C9 C10 C11 120(2) . . ? C12 C11 C10 119(2) . . ? C11 C12 C13 122(2) . . ? C8 C13 C12 120(2) . . ? C19 C14 C15 122(2) . . ? C19 C14 C1 119.3(16) . . ? C15 C14 C1 118.7(17) . . ? C16 C15 C14 120(2) . . ? C17 C16 C15 119(2) . . ? C16 C17 C18 119(2) . . ? C19 C18 C17 123(2) . . ? C18 C19 C14 116.4(19) . . ? N1 C20 C23 61.9(14) . . ? N1 C20 C21 116.6(19) . . ? C23 C20 C21 109.2(17) . . ? N2 C21 C20 105.2(16) . . ? C24 C22 C23 115.3(17) . . ? C24 C22 N2 110.0(17) . . ? C23 C22 N2 100.7(15) . . ? C24 C22 C25 112.5(17) . . ? C23 C22 C25 113.2(17) . . ? N2 C22 C25 103.8(15) . . ? C20 C23 N1 57.1(13) . . ? C20 C23 C22 111.7(18) . . ? N1 C23 C22 111.6(17) . . ? N3 C24 C22 176(2) . . ? O1 C25 C32 111.8(15) . . ? O1 C25 C22 105.3(14) . . ? C32 C25 C22 114.3(16) . . ? O1 C25 C26 108.8(14) . . ? C32 C25 C26 115.8(15) . . ? C22 C25 C26 99.8(14) . . ? C27 C26 C28 123(2) . . ? C27 C26 C25 105.7(17) . . ? C28 C26 C25 130.6(17) . . ? C26 C27 N2 120.2(19) . . ? C26 C27 C31 120(2) . . ? N2 C27 C31 119.9(19) . . ? O4 C28 C26 121.0(19) . . ? O4 C28 C29 123(2) . . ? C26 C28 C29 116(2) . . ? C30 C29 C28 128(2) . . ? C30 C29 O5 117(2) . . ? C28 C29 O5 115(2) . . ? C29 C30 C31 115(2) . . ? C29 C30 C34 127(2) . . ? C31 C30 C34 117.8(19) . . ? O3 C31 C30 121(2) . . ? O3 C31 C27 121(2) . . ? C30 C31 C27 118(2) . . ? O2 C32 C25 109.8(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 O1 H1A O2 0.84 1.88 2.697(18) 163.2 3_557 O2 H2A O4 0.84 2.87 3.297(18) 113.3 3_547 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 16.55 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.509 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.074