Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Gibson, S.' 'Jones, Jerome O.' 'Kalindjian, S. Barret' 'Knight, Jamie D.' 'Steed, Jonathan W.' 'Tozer, Matthew J.' _publ_contact_author_name 'Prof S Gibson' _publ_contact_author_address ; Department of Chemistry King's College London Strand London WC2R 2LS UK ; _publ_contact_author_email 'SUSAN.GIBSON@KCL.AC.UK' _publ_requested_journal 'Chemical Communications' _publ_section_title ; Synthesis and Structural Analysis of Dehydrophenylalanine Cyclophanes ; data_jk126 _database_code_CSD 188015 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H58 N2 O8' _chemical_formula_weight 718.90 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1007(7) _cell_length_b 9.9502(7) _cell_length_c 11.8468(8) _cell_angle_alpha 74.339(5) _cell_angle_beta 80.254(4) _cell_angle_gamma 81.103(4) _cell_volume 1011.31(13) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type Scalepack _exptl_absorpt_correction_T_min 0.9801 _exptl_absorpt_correction_T_max 0.9920 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 KappaCCD _diffrn_measurement_method '2o phi+omega frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5761 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0679 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 24.81 _reflns_number_total 3435 _reflns_number_gt 2577 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed (Barbour, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.1366P] 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_coef 0.027(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3435 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0659 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.30104(14) 0.71128(13) 0.08679(10) 0.0328(3) Uani 1 1 d . . . N1 N 0.48405(14) 0.71875(13) 0.19326(11) 0.0202(3) Uani 1 1 d . . . C1 C 1.16739(19) 0.96161(18) -0.24306(16) 0.0296(4) Uani 1 1 d . . . H1A H 1.1894 1.0386 -0.3143 0.036 Uiso 1 1 calc R . . H1B H 1.2210 0.9726 -0.1806 0.036 Uiso 1 1 calc R . . O2 O 0.30015(12) 0.58360(11) 0.27746(9) 0.0226(3) Uani 1 1 d . . . C2 C 0.99757(19) 0.97551(18) -0.20086(15) 0.0278(4) Uani 1 1 d . . . H2A H 0.9653 1.0718 -0.1909 0.033 Uiso 1 1 calc R . . H2B H 0.9445 0.9632 -0.2632 0.033 Uiso 1 1 calc R . . O3 O 0.57922(13) 0.81647(12) 0.44067(10) 0.0299(3) Uani 1 1 d . . . C3 C 0.94988(18) 0.87093(17) -0.08547(14) 0.0239(4) Uani 1 1 d . . . H3A H 1.0057 0.8794 -0.0234 0.029 Uiso 1 1 calc R . . H3B H 0.9756 0.7743 -0.0961 0.029 Uiso 1 1 calc R . . O4 O 0.40304(12) 0.90966(11) 0.32041(10) 0.0259(3) Uani 1 1 d . . . C4 C 0.78224(18) 0.89596(17) -0.04583(14) 0.0247(4) Uani 1 1 d . . . H4A H 0.7281 0.8976 -0.1120 0.030 Uiso 1 1 calc R . . H4B H 0.7594 0.9898 -0.0292 0.030 Uiso 1 1 calc R . . C5 C 0.72171(17) 0.78762(17) 0.06319(14) 0.0234(4) Uani 1 1 d . . . H5A H 0.7402 0.6934 0.0471 0.028 Uiso 1 1 calc R . . H5B H 0.7747 0.7845 0.1304 0.028 Uiso 1 1 calc R . . C6 C 0.55434(18) 0.82513(17) 0.09541(14) 0.0233(4) Uani 1 1 d . . . H6A H 0.5380 0.9158 0.1177 0.028 Uiso 1 1 calc R . . H6B H 0.5040 0.8380 0.0248 0.028 Uiso 1 1 calc R . . C7 C 0.35490(17) 0.67454(16) 0.17850(14) 0.0213(4) Uani 1 1 d . . . C8 C 0.17566(19) 0.50539(17) 0.27364(15) 0.0267(4) Uani 1 1 d . . . C9 C 0.1603(2) 0.40627(18) 0.39626(16) 0.0326(5) Uani 1 1 d . . . H9A H 0.2551 0.3459 0.4083 0.049 Uiso 1 1 calc R . . H9B H 0.0800 0.3479 0.4039 0.049 Uiso 1 1 calc R . . H9C H 0.1360 0.4610 0.4558 0.049 Uiso 1 1 calc R . . C10 C 0.2206(3) 0.4225(2) 0.18059(18) 0.0447(6) Uani 1 1 d . . . H10A H 0.2253 0.4873 0.1017 0.067 Uiso 1 1 calc R . . H10B H 0.1463 0.3578 0.1889 0.067 Uiso 1 1 calc R . . H10C H 0.3193 0.3689 0.1910 0.067 Uiso 1 1 calc R . . C11 C 0.0334(2) 0.6060(2) 0.25445(19) 0.0433(6) Uani 1 1 d . . . H11A H 0.0148 0.6627 0.3125 0.065 Uiso 1 1 calc R . . H11B H -0.0515 0.5524 0.2641 0.065 Uiso 1 1 calc R . . H11C H 0.0452 0.6679 0.1744 0.065 Uiso 1 1 calc R . . C12 C 0.53593(17) 0.69089(17) 0.30534(13) 0.0196(4) Uani 1 1 d . . . C13 C 0.51075(18) 0.80963(17) 0.36356(14) 0.0221(4) Uani 1 1 d . . . C14 C 0.3804(2) 1.03242(18) 0.36715(16) 0.0310(4) Uani 1 1 d . . . H14A H 0.3623 1.0035 0.4537 0.046 Uiso 1 1 calc R . . H14B H 0.2935 1.0949 0.3373 0.046 Uiso 1 1 calc R . . H14C H 0.4700 1.0821 0.3421 0.046 Uiso 1 1 calc R . . C15 C 0.60961(17) 0.56991(17) 0.36005(14) 0.0206(4) Uani 1 1 d . . . H15 H 0.6337 0.5698 0.4350 0.025 Uiso 1 1 calc R . . C16 C 0.65972(17) 0.43798(17) 0.32564(14) 0.0208(4) Uani 1 1 d . . . C17 C 0.73903(18) 0.33065(17) 0.40390(14) 0.0230(4) Uani 1 1 d . . . H17 H 0.7544 0.3454 0.4768 0.028 Uiso 1 1 calc R . . C18 C 0.79514(18) 0.20430(17) 0.37708(15) 0.0261(4) Uani 1 1 d . . . H18 H 0.8495 0.1343 0.4314 0.031 Uiso 1 1 calc R . . C19 C 0.77363(18) 0.17736(17) 0.27196(15) 0.0250(4) Uani 1 1 d . . . C20 C 0.69547(18) 0.28393(18) 0.19357(15) 0.0271(4) Uani 1 1 d . . . H20 H 0.6801 0.2686 0.1209 0.033 Uiso 1 1 calc R . . C21 C 0.64015(18) 0.41071(18) 0.21934(14) 0.0247(4) Uani 1 1 d . . . H21 H 0.5877 0.4811 0.1640 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 O1 0.0351(7) 0.0399(8) 0.0252(7) -0.0008(6) -0.0150(5) -0.0111(6) N1 0.0180(7) 0.0238(7) 0.0187(7) -0.0033(6) -0.0047(5) -0.0038(6) C1 0.0265(10) 0.0251(9) 0.0360(10) -0.0070(8) 0.0026(8) -0.0078(8) O2 0.0198(6) 0.0257(6) 0.0240(6) -0.0043(5) -0.0056(5) -0.0084(5) C2 0.0258(10) 0.0233(9) 0.0327(10) -0.0080(8) 0.0013(7) -0.0020(7) O3 0.0314(7) 0.0298(7) 0.0340(7) -0.0119(6) -0.0142(6) -0.0021(5) C3 0.0232(9) 0.0219(9) 0.0279(9) -0.0086(7) -0.0021(7) -0.0037(7) O4 0.0270(7) 0.0232(6) 0.0302(6) -0.0106(5) -0.0089(5) 0.0016(5) C4 0.0222(9) 0.0255(9) 0.0256(9) -0.0060(8) -0.0031(7) -0.0012(7) C5 0.0200(9) 0.0240(9) 0.0256(9) -0.0061(7) -0.0023(7) -0.0018(7) C6 0.0219(9) 0.0245(9) 0.0218(8) -0.0026(7) -0.0035(7) -0.0030(7) C7 0.0203(9) 0.0227(9) 0.0218(9) -0.0068(7) -0.0036(7) -0.0021(7) C8 0.0228(9) 0.0256(9) 0.0350(10) -0.0044(8) -0.0119(7) -0.0097(7) C9 0.0284(10) 0.0296(10) 0.0394(10) 0.0006(9) -0.0114(8) -0.0111(8) C10 0.0599(14) 0.0388(12) 0.0446(12) -0.0137(10) -0.0152(10) -0.0188(10) C11 0.0236(10) 0.0395(11) 0.0598(13) 0.0097(10) -0.0165(9) -0.0102(8) C12 0.0148(8) 0.0246(9) 0.0204(8) -0.0051(7) -0.0035(6) -0.0052(7) C13 0.0206(9) 0.0224(9) 0.0231(9) -0.0034(7) -0.0032(7) -0.0053(7) C14 0.0339(11) 0.0246(9) 0.0372(10) -0.0124(8) -0.0060(8) -0.0015(8) C15 0.0168(9) 0.0264(9) 0.0202(8) -0.0064(7) -0.0025(6) -0.0066(7) C16 0.0157(8) 0.0246(9) 0.0226(8) -0.0054(7) -0.0010(6) -0.0062(7) C17 0.0224(9) 0.0248(9) 0.0218(8) -0.0036(7) -0.0046(7) -0.0053(7) C18 0.0227(9) 0.0240(9) 0.0294(9) -0.0028(8) -0.0040(7) -0.0027(7) C19 0.0188(9) 0.0256(9) 0.0300(9) -0.0079(8) 0.0043(7) -0.0073(7) C20 0.0240(10) 0.0334(10) 0.0259(9) -0.0121(8) -0.0016(7) -0.0030(8) C21 0.0217(9) 0.0278(9) 0.0243(9) -0.0062(8) -0.0040(7) -0.0014(7) _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 C7 1.2103(18) . ? N1 C7 1.370(2) . ? N1 C12 1.4268(19) . ? N1 C6 1.4729(19) . ? C1 C19 1.510(2) 2_765 ? C1 C2 1.539(2) . ? O2 C7 1.3455(18) . ? O2 C8 1.4834(19) . ? C2 C3 1.520(2) . ? O3 C13 1.2111(19) . ? C3 C4 1.521(2) . ? O4 C13 1.3439(19) . ? O4 C14 1.446(2) . ? C4 C5 1.525(2) . ? C5 C6 1.520(2) . ? C8 C10 1.515(3) . ? C8 C9 1.517(2) . ? C8 C11 1.519(2) . ? C12 C15 1.340(2) . ? C12 C13 1.492(2) . ? C15 C16 1.462(2) . ? C16 C21 1.402(2) . ? C16 C17 1.405(2) . ? C17 C18 1.380(2) . ? C18 C19 1.393(2) . ? C19 C20 1.397(2) . ? C19 C1 1.510(2) 2_765 ? C20 C21 1.378(2) . ? 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 C7 N1 C12 123.18(12) . . ? C7 N1 C6 118.13(12) . . ? C12 N1 C6 117.29(13) . . ? C19 C1 C2 113.17(14) 2_765 . ? C7 O2 C8 119.34(12) . . ? C3 C2 C1 114.39(14) . . ? C2 C3 C4 111.47(13) . . ? C13 O4 C14 115.10(13) . . ? C3 C4 C5 115.12(13) . . ? C6 C5 C4 110.26(13) . . ? N1 C6 C5 113.76(12) . . ? O1 C7 O2 125.45(15) . . ? O1 C7 N1 123.48(14) . . ? O2 C7 N1 111.05(12) . . ? O2 C8 C10 110.14(14) . . ? O2 C8 C9 102.28(12) . . ? C10 C8 C9 110.17(15) . . ? O2 C8 C11 109.90(14) . . ? C10 C8 C11 112.96(16) . . ? C9 C8 C11 110.88(15) . . ? C15 C12 N1 125.75(15) . . ? C15 C12 C13 117.65(14) . . ? N1 C12 C13 116.55(13) . . ? O3 C13 O4 123.31(16) . . ? O3 C13 C12 124.38(15) . . ? O4 C13 C12 112.31(13) . . ? C12 C15 C16 131.86(15) . . ? C21 C16 C17 116.97(16) . . ? C21 C16 C15 125.70(14) . . ? C17 C16 C15 117.30(15) . . ? C18 C17 C16 121.40(16) . . ? C17 C18 C19 121.28(15) . . ? C18 C19 C20 117.57(16) . . ? C18 C19 C1 121.51(15) . 2_765 ? C20 C19 C1 120.92(16) . 2_765 ? C21 C20 C19 121.46(16) . . ? C20 C21 C16 121.31(15) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 24.81 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.214 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.061 data_jj291 _database_code_CSD 188016 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H25 N O4' _chemical_formula_weight 331.40 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.068(2) _cell_length_b 10.189(3) _cell_length_c 11.317(3) _cell_angle_alpha 68.324(15) _cell_angle_beta 75.548(16) _cell_angle_gamma 77.333(15) _cell_volume 931.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type Scalepack _exptl_absorpt_correction_T_min 0.9837 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method '2o phi+omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4700 _diffrn_reflns_av_R_equivalents 0.1335 _diffrn_reflns_av_sigmaI/netI 0.1977 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3015 _reflns_number_gt 1970 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed (Barbour, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+1.6841P] 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_coef 0.025(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3015 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2153 _refine_ls_R_factor_gt 0.1500 _refine_ls_wR_factor_ref 0.2361 _refine_ls_wR_factor_gt 0.2157 _refine_ls_goodness_of_fit_ref 1.278 _refine_ls_restrained_S_all 1.278 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C19 C -0.2510(7) 0.3426(8) 0.2293(8) 0.050(2) Uani 1 1 d . . . H19A H -0.2845 0.3346 0.3207 0.075 Uiso 1 1 calc R . . H19B H -0.3248 0.3067 0.2028 0.075 Uiso 1 1 calc R . . H19C H -0.2452 0.4429 0.1764 0.075 Uiso 1 1 calc R . . O2 O 0.1412(4) 0.6327(4) 0.2424(4) 0.0258(10) Uani 1 1 d . . . O4 O 0.0223(4) 0.3182(4) 0.2372(4) 0.0278(10) Uani 1 1 d . . . O1 O 0.3619(4) 0.6173(4) 0.1008(4) 0.0275(10) Uani 1 1 d . . . N1 N 0.1533(5) 0.3549(4) 0.3622(4) 0.0187(11) Uani 1 1 d . . . O3 O -0.0827(4) 0.2806(4) 0.4509(4) 0.0290(11) Uani 1 1 d . . . C15 C 0.0193(6) 0.3152(5) 0.3579(6) 0.0211(13) Uani 1 1 d . . . C6 C 0.5423(7) -0.0390(6) 0.1631(6) 0.0290(15) Uani 1 1 d . . . H6 H 0.6160 -0.0743 0.1020 0.035 Uiso 1 1 calc R . . C12 C 0.2642(6) 0.4028(5) 0.2480(5) 0.0192(13) Uani 1 1 d . . . C8 C 0.3958(6) 0.1632(5) 0.2233(5) 0.0207(13) Uani 1 1 d . . . C5 C 0.4751(7) -0.1346(6) 0.2769(5) 0.0235(13) Uani 1 1 d . . . C7 C 0.5043(7) 0.1060(6) 0.1371(5) 0.0256(14) Uani 1 1 d . . . H7 H 0.5531 0.1687 0.0586 0.031 Uiso 1 1 calc R . . C4 C 0.5225(7) -0.2945(6) 0.3098(6) 0.0312(15) Uani 1 1 d . . . H4A H 0.5300 -0.3206 0.2323 0.037 Uiso 1 1 calc R . . H4B H 0.4419 -0.3441 0.3784 0.037 Uiso 1 1 calc R . . C13 C 0.2647(6) 0.5616(6) 0.1869(5) 0.0206(13) Uani 1 1 d . . . C11 C 0.3661(6) 0.3193(6) 0.1883(5) 0.0209(13) Uani 1 1 d . . . H11 H 0.4294 0.3692 0.1109 0.025 Uiso 1 1 calc R . . C10 C 0.3668(6) -0.0774(6) 0.3636(6) 0.0279(15) Uani 1 1 d . . . H10 H 0.3188 -0.1402 0.4425 0.033 Uiso 1 1 calc R . . C1 C 0.8331(6) -0.3782(6) 0.5205(5) 0.0245(14) Uani 1 1 d . . . H1A H 0.8482 -0.4822 0.5366 0.029 Uiso 1 1 calc R . . H1B H 0.9165 -0.3374 0.4493 0.029 Uiso 1 1 calc R . . C3 C 0.6769(7) -0.3456(6) 0.3562(5) 0.0250(14) Uani 1 1 d . . . H3A H 0.7022 -0.4499 0.3744 0.030 Uiso 1 1 calc R . . H3B H 0.7580 -0.3000 0.2854 0.030 Uiso 1 1 calc R . . C9 C 0.3281(6) 0.0677(6) 0.3377(6) 0.0252(14) Uani 1 1 d . . . H9 H 0.2542 0.1030 0.3988 0.030 Uiso 1 1 calc R . . C14 C 0.1357(7) 0.7851(5) 0.2050(6) 0.0296(15) Uani 1 1 d . . . H14A H 0.2246 0.8155 0.1371 0.044 Uiso 1 1 calc R . . H14B H 0.1383 0.8099 0.2803 0.044 Uiso 1 1 calc R . . H14C H 0.0407 0.8335 0.1724 0.044 Uiso 1 1 calc R . . C16 C -0.0933(7) 0.2554(7) 0.2105(7) 0.0366(17) Uani 1 1 d . . . C17 C -0.0935(8) 0.1017(7) 0.2962(7) 0.048(2) Uani 1 1 d . . . H17A H 0.0116 0.0509 0.2883 0.072 Uiso 1 1 calc R . . H17B H -0.1594 0.0572 0.2698 0.072 Uiso 1 1 calc R . . H17C H -0.1329 0.0971 0.3863 0.072 Uiso 1 1 calc R . . C18 C -0.0340(8) 0.2689(9) 0.0692(7) 0.058(2) Uani 1 1 d . . . H18A H -0.0290 0.3695 0.0172 0.087 Uiso 1 1 calc R . . H18B H -0.1036 0.2317 0.0394 0.087 Uiso 1 1 calc R . . H18C H 0.0690 0.2141 0.0598 0.087 Uiso 1 1 calc R . . C2 C 0.6797(6) -0.3132(6) 0.4769(5) 0.0265(14) Uani 1 1 d . . . H2A H 0.6644 -0.2087 0.4577 0.032 Uiso 1 1 calc R . . H2B H 0.5950 -0.3530 0.5471 0.032 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 C19 0.031(4) 0.055(5) 0.088(6) -0.044(4) -0.024(4) -0.004(3) O2 0.028(2) 0.022(2) 0.025(2) -0.0108(17) 0.0032(19) -0.0015(17) O4 0.019(2) 0.043(3) 0.026(2) -0.0163(19) -0.0019(19) -0.0082(19) O1 0.028(2) 0.025(2) 0.023(2) -0.0035(17) 0.003(2) -0.0054(19) N1 0.015(2) 0.025(3) 0.017(3) -0.010(2) 0.000(2) -0.003(2) O3 0.018(2) 0.037(2) 0.034(3) -0.0165(19) 0.009(2) -0.0158(18) C15 0.017(3) 0.013(3) 0.029(4) -0.005(2) -0.004(3) 0.001(2) C6 0.032(3) 0.027(3) 0.031(4) -0.016(3) -0.006(3) -0.001(3) C12 0.013(3) 0.022(3) 0.019(3) -0.002(2) -0.003(3) -0.004(2) C8 0.020(3) 0.020(3) 0.020(3) -0.001(2) -0.008(3) -0.004(2) C5 0.026(3) 0.023(3) 0.022(3) -0.004(2) -0.012(3) -0.002(2) C7 0.034(3) 0.026(3) 0.017(3) -0.010(2) 0.002(3) -0.006(3) C4 0.035(4) 0.025(3) 0.036(4) -0.012(3) -0.013(3) 0.001(3) C13 0.018(3) 0.032(3) 0.012(3) -0.007(2) -0.002(3) -0.007(3) C11 0.014(3) 0.027(3) 0.022(3) -0.007(2) -0.001(3) -0.009(2) C10 0.025(3) 0.032(4) 0.023(3) -0.004(3) -0.002(3) -0.007(3) C1 0.024(3) 0.027(3) 0.021(3) -0.011(3) -0.004(3) 0.005(3) C3 0.031(3) 0.019(3) 0.024(3) -0.009(2) -0.006(3) 0.002(3) C9 0.023(3) 0.019(3) 0.029(3) -0.007(3) -0.004(3) 0.005(2) C14 0.038(4) 0.016(3) 0.034(4) -0.013(3) -0.003(3) 0.002(3) C16 0.025(3) 0.044(4) 0.054(5) -0.030(3) -0.008(3) -0.007(3) C17 0.039(4) 0.045(4) 0.070(5) -0.037(4) 0.004(4) -0.010(3) C18 0.044(4) 0.089(6) 0.064(6) -0.046(5) -0.019(4) -0.008(4) C2 0.027(3) 0.024(3) 0.025(3) -0.006(3) -0.008(3) 0.005(3) _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 C19 C16 1.520(9) . ? O2 C13 1.343(6) . ? O2 C14 1.444(6) . ? O4 C15 1.349(7) . ? O4 C16 1.482(7) . ? O1 C13 1.196(6) . ? N1 C15 1.378(7) . ? N1 C12 1.422(7) . ? N1 C1 1.471(7) 2_656 ? O3 C15 1.213(6) . ? C6 C7 1.377(8) . ? C6 C5 1.386(8) . ? C12 C11 1.343(7) . ? C12 C13 1.507(7) . ? C8 C9 1.391(7) . ? C8 C7 1.395(7) . ? C8 C11 1.470(7) . ? C5 C10 1.399(8) . ? C5 C4 1.518(8) . ? C4 C3 1.534(8) . ? C10 C9 1.377(7) . ? C1 N1 1.471(7) 2_656 ? C1 C2 1.521(7) . ? C3 C2 1.527(8) . ? C16 C17 1.507(9) . ? C16 C18 1.519(9) . ? 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 C14 117.1(4) . . ? C15 O4 C16 121.0(4) . . ? C15 N1 C12 121.1(5) . . ? C15 N1 C1 119.3(4) . 2_656 ? C12 N1 C1 118.3(4) . 2_656 ? O3 C15 O4 126.3(5) . . ? O3 C15 N1 123.9(5) . . ? O4 C15 N1 109.8(5) . . ? C7 C6 C5 121.2(5) . . ? C11 C12 N1 125.8(5) . . ? C11 C12 C13 117.2(5) . . ? N1 C12 C13 117.0(5) . . ? C9 C8 C7 117.4(5) . . ? C9 C8 C11 125.1(5) . . ? C7 C8 C11 117.5(5) . . ? C6 C5 C10 117.2(5) . . ? C6 C5 C4 121.6(5) . . ? C10 C5 C4 121.1(5) . . ? C6 C7 C8 121.6(5) . . ? C5 C4 C3 112.6(5) . . ? O1 C13 O2 124.3(5) . . ? O1 C13 C12 124.8(5) . . ? O2 C13 C12 110.8(5) . . ? C12 C11 C8 130.5(5) . . ? C9 C10 C5 121.8(5) . . ? N1 C1 C2 114.2(4) 2_656 . ? C2 C3 C4 114.2(5) . . ? C10 C9 C8 120.8(5) . . ? O4 C16 C17 110.0(5) . . ? O4 C16 C18 101.9(5) . . ? C17 C16 C18 111.7(6) . . ? O4 C16 C19 109.8(5) . . ? C17 C16 C19 111.6(6) . . ? C18 C16 C19 111.4(6) . . ? C1 C2 C3 109.9(4) . . ? 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 C16 O4 C15 O3 -10.0(8) . . . . ? C16 O4 C15 N1 168.7(4) . . . . ? C12 N1 C15 O3 -176.0(5) . . . . ? C1 N1 C15 O3 -9.5(7) 2_656 . . . ? C12 N1 C15 O4 5.3(6) . . . . ? C1 N1 C15 O4 171.8(4) 2_656 . . . ? C15 N1 C12 C11 -78.1(7) . . . . ? C1 N1 C12 C11 115.3(6) 2_656 . . . ? C15 N1 C12 C13 100.4(6) . . . . ? C1 N1 C12 C13 -66.2(6) 2_656 . . . ? C7 C6 C5 C10 0.2(9) . . . . ? C7 C6 C5 C4 -176.6(5) . . . . ? C5 C6 C7 C8 -0.6(9) . . . . ? C9 C8 C7 C6 0.6(8) . . . . ? C11 C8 C7 C6 178.4(5) . . . . ? C6 C5 C4 C3 76.3(7) . . . . ? C10 C5 C4 C3 -100.4(6) . . . . ? C14 O2 C13 O1 -7.3(8) . . . . ? C14 O2 C13 C12 172.5(5) . . . . ? C11 C12 C13 O1 -11.1(8) . . . . ? N1 C12 C13 O1 170.3(5) . . . . ? C11 C12 C13 O2 169.1(5) . . . . ? N1 C12 C13 O2 -9.6(7) . . . . ? N1 C12 C11 C8 -2.4(10) . . . . ? C13 C12 C11 C8 179.1(5) . . . . ? C9 C8 C11 C12 -6.3(9) . . . . ? C7 C8 C11 C12 176.1(6) . . . . ? C6 C5 C10 C9 0.0(9) . . . . ? C4 C5 C10 C9 176.9(6) . . . . ? C5 C4 C3 C2 59.5(7) . . . . ? C5 C10 C9 C8 0.1(9) . . . . ? C7 C8 C9 C10 -0.4(8) . . . . ? C11 C8 C9 C10 -178.0(5) . . . . ? C15 O4 C16 C17 -55.3(7) . . . . ? C15 O4 C16 C18 -173.9(5) . . . . ? C15 O4 C16 C19 67.9(7) . . . . ? N1 C1 C2 C3 -179.1(5) 2_656 . . . ? C4 C3 C2 C1 175.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.918 _refine_diff_density_max 0.271 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.059 data_jk150a _database_code_CSD 189757 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H78.10 Cl3.90 N2 O8.70' _chemical_formula_weight 1008.72 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1987(4) _cell_length_b 8.8260(6) _cell_length_c 20.8707(13) _cell_angle_alpha 101.52(4) _cell_angle_beta 91.999(4) _cell_angle_gamma 113.079(3) _cell_volume 1350.58(14) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 0.268 _exptl_absorpt_correction_type Scalepack _exptl_absorpt_correction_T_min 0.9484 _exptl_absorpt_correction_T_max 0.9737 _exptl_absorpt_process_details 'Otwinowski & Minor, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7441 _diffrn_reflns_av_R_equivalents 0.0937 _diffrn_reflns_av_sigmaI/netI 0.1472 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4708 _reflns_number_gt 3141 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed (Barbour, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+10.5529P] 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_coef 0.011(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4708 _refine_ls_number_parameters 302 _refine_ls_number_restraints 180 _refine_ls_R_factor_all 0.1836 _refine_ls_R_factor_gt 0.1299 _refine_ls_wR_factor_ref 0.2976 _refine_ls_wR_factor_gt 0.2724 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.9802(6) 0.8122(6) 0.2134(2) 0.0275(11) Uani 1 1 d U A . O2 O 1.0496(6) 0.7425(5) 0.3054(2) 0.0222(10) Uani 1 1 d U A . O3 O 0.7153(6) 0.3616(6) 0.3694(2) 0.0299(12) Uani 1 1 d U . . O4 O 0.6311(6) 0.5389(5) 0.32450(19) 0.0201(10) Uani 1 1 d U . . N1 N 0.8029(6) 0.4262(6) 0.2726(2) 0.0153(11) Uani 1 1 d U . . C1 C -0.9292(8) -1.3439(8) -0.2694(3) 0.0210(14) Uani 1 1 d U . . H1A H -1.0480 -1.4258 -0.2634 0.025 Uiso 1 1 calc R . . H1B H -0.9414 -1.3131 -0.3118 0.025 Uiso 1 1 calc R . . C2 C -0.8712(8) -1.1864(8) -0.2140(3) 0.0213(14) Uani 1 1 d U . . H2A H -0.8452 -1.2150 -0.1724 0.026 Uiso 1 1 calc R . . H2B H -0.9718 -1.1514 -0.2091 0.026 Uiso 1 1 calc R . . C3 C -0.7070(8) -1.0369(7) -0.2241(3) 0.0184(13) Uani 1 1 d U . . H3A H -0.6178 -1.0783 -0.2419 0.022 Uiso 1 1 calc R . . H3B H -0.7423 -0.9845 -0.2568 0.022 Uiso 1 1 calc R . . C4 C -0.6223(8) -0.9035(8) -0.1597(3) 0.0202(14) Uani 1 1 d U . . H4A H -0.5904 -0.9583 -0.1272 0.024 Uiso 1 1 calc R . . H4B H -0.7131 -0.8638 -0.1423 0.024 Uiso 1 1 calc R . . C5 C -0.4553(8) -0.7486(8) -0.1645(3) 0.0203(14) Uani 1 1 d U . . H5A H -0.3660 -0.7863 -0.1847 0.024 Uiso 1 1 calc R . . H5B H -0.4875 -0.6851 -0.1931 0.024 Uiso 1 1 calc R . . C6 C -0.3748(8) -0.6335(8) -0.0964(3) 0.0210(14) Uani 1 1 d U . . H6A H -0.3489 -0.7009 -0.0681 0.025 Uiso 1 1 calc R . . H6B H -0.4661 -0.5972 -0.0773 0.025 Uiso 1 1 calc R . . C7 C -0.2043(8) -0.4753(7) -0.0932(3) 0.0171(13) Uani 1 1 d U . . H7A H -0.1116 -0.5085 -0.1129 0.021 Uiso 1 1 calc R . . H7B H -0.2290 -0.4023 -0.1191 0.021 Uiso 1 1 calc R . . C8 C -0.1364(8) -0.3775(8) -0.0222(3) 0.0181(13) Uani 1 1 d U . . H8A H -0.1185 -0.4548 0.0030 0.022 Uiso 1 1 calc R . . H8B H -0.2311 -0.3456 -0.0038 0.022 Uiso 1 1 calc R . . C9 C 0.0369(8) -0.2172(7) -0.0103(3) 0.0160(13) Uani 1 1 d U . . H9A H 0.1357 -0.2462 -0.0263 0.019 Uiso 1 1 calc R . . H9B H 0.0227 -0.1369 -0.0348 0.019 Uiso 1 1 calc R . . C10 C 0.0798(8) -0.1361(8) 0.0633(3) 0.0177(13) Uani 1 1 d U A . H10A H 0.0858 -0.2220 0.0863 0.021 Uiso 1 1 calc R . . H10B H -0.0222 -0.1102 0.0776 0.021 Uiso 1 1 calc R . . C11 C 0.2501(7) 0.0246(7) 0.0876(3) 0.0145(13) Uani 1 1 d U . . C12 C 0.2894(8) 0.0936(7) 0.1553(3) 0.0158(13) Uani 1 1 d U A 1 H12 H 0.2102 0.0392 0.1838 0.019 Uiso 1 1 calc R . . C13 C 0.4386(8) 0.2370(7) 0.1820(3) 0.0165(13) Uani 1 1 d U . . H13 H 0.4620 0.2787 0.2284 0.020 Uiso 1 1 calc R A 1 C14 C 0.5575(8) 0.3238(7) 0.1420(3) 0.0162(13) Uani 1 1 d U A . C15 C 0.5160(8) 0.2577(8) 0.0740(3) 0.0184(14) Uani 1 1 d U . . H15 H 0.5919 0.3156 0.0454 0.022 Uiso 1 1 calc R A . C16 C 0.3673(7) 0.1103(7) 0.0472(3) 0.0148(13) Uani 1 1 d U A . H16 H 0.3446 0.0668 0.0008 0.018 Uiso 1 1 calc R . . C17 C 0.7140(8) 0.4826(8) 0.1694(3) 0.0188(14) Uani 1 1 d U . . H17 H 0.7475 0.5612 0.1420 0.023 Uiso 1 1 calc R A . C18 C 0.8158(8) 0.5319(7) 0.2274(3) 0.0149(13) Uani 1 1 d U A . C19 C 0.9565(8) 0.7090(8) 0.2466(3) 0.0179(13) Uani 1 1 d U . . C20 C 1.1820(9) 0.9149(8) 0.3276(3) 0.0305(17) Uani 1 1 d U . . H20A H 1.2760 0.9355 0.2986 0.046 Uiso 1 1 calc R A . H20B H 1.2347 0.9324 0.3728 0.046 Uiso 1 1 calc R . . H20C H 1.1251 0.9936 0.3265 0.046 Uiso 1 1 calc R . . C21 C 0.7170(8) 0.4360(8) 0.3268(3) 0.0176(13) Uani 1 1 d U . . C22 C 0.5147(9) 0.5610(9) 0.3746(3) 0.0273(16) Uani 1 1 d U . . C23 C 0.4452(10) 0.6782(9) 0.3506(3) 0.0318(17) Uani 1 1 d U . . H23A H 0.5457 0.7848 0.3501 0.048 Uiso 1 1 calc R . . H23B H 0.3633 0.7013 0.3803 0.048 Uiso 1 1 calc R . . H23C H 0.3816 0.6245 0.3060 0.048 Uiso 1 1 calc R . . C24 C 0.6244(11) 0.6443(10) 0.4425(3) 0.0381(19) Uani 1 1 d U . . H24A H 0.6656 0.5650 0.4571 0.057 Uiso 1 1 calc R . . H24B H 0.5501 0.6746 0.4740 0.057 Uiso 1 1 calc R . . H24C H 0.7278 0.7466 0.4399 0.057 Uiso 1 1 calc R . . C25 C 0.3617(9) 0.3903(9) 0.3736(3) 0.0332(17) Uani 1 1 d U . . H25A H 0.2943 0.3418 0.3294 0.050 Uiso 1 1 calc R . . H25B H 0.2821 0.4070 0.4056 0.050 Uiso 1 1 calc R . . H25C H 0.4108 0.3130 0.3852 0.050 Uiso 1 1 calc R . . Cl1S Cl 0.6089(5) 0.0518(5) 0.48748(17) 0.0555(10) Uiso 0.65 1 d P . 1 Cl3S Cl 0.9345(6) 0.0973(5) 0.4277(2) 0.0681(11) Uiso 0.65 1 d P B 1 Cl2S Cl 0.9364(6) 0.3440(5) 0.5411(2) 0.0681(11) Uiso 0.65 1 d P B 1 C1S C 0.792(3) 0.185(2) 0.4666(9) 0.065(5) Uiso 0.65 1 d P B 1 H1S H 0.7581 0.2461 0.4367 0.078 Uiso 0.65 1 calc PR B 1 O1S O 0.717(2) 0.238(2) 0.4844(9) 0.058(5) Uiso 0.35 1 d P C 2 H1S1 H 0.7313 0.3266 0.5123 0.070 Uiso 0.35 1 calc PR C 2 C2S C 0.873(4) 0.221(3) 0.4828(13) 0.040(6) Uiso 0.35 1 d P C 2 H2S1 H 0.9717 0.3332 0.4969 0.060 Uiso 0.35 1 calc PR C 2 H2S2 H 0.8810 0.1683 0.4379 0.060 Uiso 0.35 1 calc PR C 2 H2S3 H 0.8786 0.1503 0.5127 0.060 Uiso 0.35 1 calc PR C 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 O1 0.021(2) 0.023(3) 0.030(3) 0.012(2) -0.002(2) -0.002(2) O2 0.023(2) 0.014(2) 0.023(2) 0.0033(18) -0.0047(19) 0.0017(19) O3 0.042(3) 0.032(3) 0.022(2) 0.017(2) 0.005(2) 0.017(2) O4 0.025(2) 0.023(2) 0.015(2) 0.0047(18) 0.0052(18) 0.012(2) N1 0.014(2) 0.011(3) 0.020(3) 0.006(2) 0.000(2) 0.003(2) C1 0.015(3) 0.016(3) 0.031(4) 0.010(3) -0.003(3) 0.003(3) C2 0.021(3) 0.022(3) 0.022(3) 0.005(3) 0.004(3) 0.010(3) C3 0.018(3) 0.014(3) 0.022(3) -0.001(3) 0.001(3) 0.008(3) C4 0.022(3) 0.020(3) 0.020(3) 0.007(3) 0.006(3) 0.010(3) C5 0.024(3) 0.018(3) 0.017(3) 0.003(3) 0.002(3) 0.006(3) C6 0.023(3) 0.018(3) 0.022(3) 0.006(3) 0.004(3) 0.008(3) C7 0.014(3) 0.015(3) 0.022(3) 0.002(3) -0.001(2) 0.008(3) C8 0.020(3) 0.022(3) 0.015(3) 0.002(3) 0.002(2) 0.013(3) C9 0.018(3) 0.017(3) 0.016(3) 0.006(2) 0.004(2) 0.009(3) C10 0.016(3) 0.018(3) 0.019(3) 0.006(3) 0.003(2) 0.006(3) C11 0.011(3) 0.015(3) 0.020(3) 0.002(2) -0.001(2) 0.008(2) C12 0.016(3) 0.016(3) 0.016(3) 0.010(2) 0.002(2) 0.005(3) C13 0.016(3) 0.017(3) 0.015(3) 0.003(2) -0.001(2) 0.005(3) C14 0.012(3) 0.016(3) 0.022(3) 0.008(3) 0.001(2) 0.006(3) C15 0.018(3) 0.022(3) 0.019(3) 0.013(3) 0.009(3) 0.008(3) C16 0.015(3) 0.015(3) 0.014(3) 0.002(2) -0.002(2) 0.006(3) C17 0.016(3) 0.023(3) 0.022(3) 0.007(3) 0.005(3) 0.011(3) C18 0.015(3) 0.014(3) 0.019(3) 0.007(2) 0.005(2) 0.007(3) C19 0.020(3) 0.018(3) 0.017(3) 0.004(3) 0.004(3) 0.009(3) C20 0.030(4) 0.017(4) 0.028(4) -0.003(3) -0.012(3) -0.003(3) C21 0.017(3) 0.016(3) 0.017(3) 0.004(3) 0.001(2) 0.004(3) C22 0.032(4) 0.042(4) 0.017(3) 0.013(3) 0.012(3) 0.021(3) C23 0.038(4) 0.041(4) 0.022(4) 0.006(3) 0.006(3) 0.022(4) C24 0.053(5) 0.046(5) 0.021(4) 0.001(3) 0.005(3) 0.030(4) C25 0.025(4) 0.041(4) 0.029(4) 0.008(3) 0.006(3) 0.008(3) _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 C19 1.212(7) . ? O2 C19 1.338(7) . ? O2 C20 1.448(7) . ? O3 C21 1.203(7) . ? O4 C21 1.356(7) . ? O4 C22 1.475(7) . ? N1 C21 1.360(7) . ? N1 C18 1.432(7) . ? N1 C1 1.476(8) 2_545 ? C1 N1 1.476(8) 2_545 ? C1 C2 1.516(9) . ? C2 C3 1.529(8) . ? C3 C4 1.529(8) . ? C4 C5 1.533(8) . ? C5 C6 1.523(9) . ? C6 C7 1.528(8) . ? C7 C8 1.519(8) . ? C8 C9 1.530(8) . ? C9 C10 1.525(8) . ? C10 C11 1.526(8) . ? C11 C12 1.393(8) . ? C11 C16 1.396(8) . ? C12 C13 1.365(8) . ? C13 C14 1.399(8) . ? C14 C15 1.397(8) . ? C14 C17 1.468(9) . ? C15 C16 1.382(8) . ? C17 C18 1.337(8) . ? C18 C19 1.496(8) . ? C22 C23 1.515(9) . ? C22 C24 1.527(10) . ? C22 C25 1.532(10) . ? Cl1S C1S 1.642(19) . ? Cl1S Cl1S 1.809(7) 2_656 ? Cl3S C1S 1.77(2) . ? Cl2S C1S 1.867(19) . ? O1S C2S 1.34(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 C19 O2 C20 114.6(5) . . ? C21 O4 C22 120.9(5) . . ? C21 N1 C18 121.8(5) . . ? C21 N1 C1 119.2(5) . 2_545 ? C18 N1 C1 116.5(5) . 2_545 ? N1 C1 C2 113.1(5) 2_545 . ? C1 C2 C3 114.3(5) . . ? C4 C3 C2 111.7(5) . . ? C3 C4 C5 115.7(5) . . ? C6 C5 C4 110.5(5) . . ? C5 C6 C7 116.4(5) . . ? C8 C7 C6 110.3(5) . . ? C7 C8 C9 116.9(5) . . ? C10 C9 C8 108.8(5) . . ? C9 C10 C11 118.5(5) . . ? C12 C11 C16 117.4(5) . . ? C12 C11 C10 117.5(5) . . ? C16 C11 C10 125.0(5) . . ? C13 C12 C11 122.0(5) . . ? C12 C13 C14 121.2(5) . . ? C15 C14 C13 117.0(5) . . ? C15 C14 C17 120.8(5) . . ? C13 C14 C17 122.1(5) . . ? C16 C15 C14 121.7(5) . . ? C15 C16 C11 120.7(5) . . ? C18 C17 C14 129.0(6) . . ? C17 C18 N1 124.8(5) . . ? C17 C18 C19 118.2(5) . . ? N1 C18 C19 117.0(5) . . ? O1 C19 O2 123.7(6) . . ? O1 C19 C18 123.8(6) . . ? O2 C19 C18 112.4(5) . . ? O3 C21 O4 125.7(6) . . ? O3 C21 N1 124.7(6) . . ? O4 C21 N1 109.5(5) . . ? O4 C22 C23 101.9(5) . . ? O4 C22 C24 110.2(5) . . ? C23 C22 C24 111.2(6) . . ? O4 C22 C25 110.0(5) . . ? C23 C22 C25 110.9(6) . . ? C24 C22 C25 112.1(6) . . ? C1S Cl1S Cl1S 165.9(8) . 2_656 ? Cl1S C1S Cl3S 116.6(11) . . ? Cl1S C1S Cl2S 110.4(10) . . ? Cl3S C1S Cl2S 104.3(10) . . ? 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 C1S H1S O3 1.00 1.99 2.98(2) 171.8 . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.680 _refine_diff_density_min -0.954 _refine_diff_density_rms 0.122