# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Xumu Zhang' _publ_contact_author_address ; Department of Chemistry The Pennsylvania State University 104 Chemistry Research Building University Park PA 16802 UNITED STATES OF AMERICA ; _publ_contact_author_email XUMU@CHEM.PSU.EDU _publ_section_title ; Practical Synthesis of Chiral 9,9'-Spirobixanthene-1,1'-diol ; loop_ _publ_author_name 'Xumu Zhang' 'Shulin Wu' 'Weicheng Zhang' 'Zhaoguo Zhang' # Attachment 'suw8s3.cif' data_suw8s _database_code_depnum_ccdc_archive 'CCDC 616446' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H29 N2 O, C25 H16 O4, C2 H3 N, Cl' _chemical_formula_sum 'C53 H48 Cl N3 O5' _chemical_formula_weight 842.39 _chemical_absolute_configuration rm 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 Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 14.322(4) _cell_length_b 8.975(2) _cell_length_c 17.157(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.742(5) _cell_angle_gamma 90.00 _cell_volume 2185.2(10) _cell_formula_units_Z 2 _cell_measurement_temperature 95(2) _cell_measurement_reflns_used 2524 _cell_measurement_theta_min 2.395 _cell_measurement_theta_max 28.125 _exptl_crystal_description flat-needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.969 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 95(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_reflns_number 13563 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.1260 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.20 _diffrn_reflns_theta_max 28.30 _reflns_number_total 9403 _reflns_number_gt 6628 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0443P)^2^+0.8947P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(8) _refine_ls_number_reflns 9403 _refine_ls_number_parameters 563 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1015 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1637 _refine_ls_wR_factor_gt 0.1314 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.002 _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 C1 C 0.7996(2) 0.6830(4) 0.2674(2) 0.0167(8) Uani 1 1 d . . . C2 C 0.8172(3) 0.7662(4) 0.3361(2) 0.0217(8) Uani 1 1 d . . . H2A H 0.7702 0.7755 0.3700 0.026 Uiso 1 1 calc R . . C3 C 0.9036(3) 0.8356(4) 0.3547(3) 0.0247(9) Uani 1 1 d . . . H3 H 0.9156 0.8928 0.4015 0.030 Uiso 1 1 calc R . . C4 C 0.9719(3) 0.8229(4) 0.3066(3) 0.0233(9) Uani 1 1 d . . . H4 H 1.0316 0.8690 0.3202 0.028 Uiso 1 1 calc R . . C5 C 0.9525(3) 0.7411(4) 0.2372(2) 0.0200(8) Uani 1 1 d . . . C6 C 0.8676(2) 0.6667(4) 0.2159(2) 0.0178(7) Uani 1 1 d . . . C7 C 0.8500(3) 0.5698(4) 0.1428(2) 0.0175(8) Uani 1 1 d . . . C8 C 0.9327(3) 0.5839(4) 0.0951(2) 0.0206(8) Uani 1 1 d . . . C9 C 0.9291(3) 0.5158(4) 0.0221(3) 0.0266(9) Uani 1 1 d . . . H9 H 0.8742 0.4617 0.0017 0.032 Uiso 1 1 calc R . . C10 C 1.0032(3) 0.5244(5) -0.0220(3) 0.0318(10) Uani 1 1 d . . . H10 H 0.9991 0.4770 -0.0718 0.038 Uiso 1 1 calc R . . C11 C 1.0834(3) 0.6031(5) 0.0077(3) 0.0339(11) Uani 1 1 d . . . H11 H 1.1348 0.6093 -0.0219 0.041 Uiso 1 1 calc R . . C12 C 1.0892(3) 0.6720(4) 0.0794(3) 0.0288(9) Uani 1 1 d . . . H12 H 1.1445 0.7252 0.0997 0.035 Uiso 1 1 calc R . . C13 C 1.0140(3) 0.6637(4) 0.1222(2) 0.0235(8) Uani 1 1 d . . . C14 C 0.7602(3) 0.6200(4) 0.0925(2) 0.0176(8) Uani 1 1 d . . . C15 C 0.7472(3) 0.7703(4) 0.0708(2) 0.0215(8) Uani 1 1 d . . . H15 H 0.7968 0.8392 0.0857 0.026 Uiso 1 1 calc R . . C16 C 0.6645(3) 0.8207(5) 0.0285(3) 0.0293(10) Uani 1 1 d . . . H16 H 0.6573 0.9229 0.0147 0.035 Uiso 1 1 calc R . . C17 C 0.5922(3) 0.7212(5) 0.0064(3) 0.0300(10) Uani 1 1 d . . . H17 H 0.5347 0.7556 -0.0219 0.036 Uiso 1 1 calc R . . C18 C 0.6030(3) 0.5720(5) 0.0253(2) 0.0267(9) Uani 1 1 d . . . H18 H 0.5535 0.5035 0.0097 0.032 Uiso 1 1 calc R . . C19 C 0.6867(3) 0.5237(4) 0.0672(2) 0.0209(8) Uani 1 1 d . . . C20 C 0.7659(3) 0.3169(4) 0.1328(2) 0.0181(8) Uani 1 1 d . . . C21 C 0.7604(2) 0.1655(4) 0.1484(2) 0.0202(8) Uani 1 1 d . . . H21 H 0.7089 0.1081 0.1240 0.024 Uiso 1 1 calc R . . C22 C 0.8306(3) 0.0997(4) 0.1998(2) 0.0209(8) Uani 1 1 d . . . H22 H 0.8268 -0.0033 0.2117 0.025 Uiso 1 1 calc R . . C23 C 0.9060(3) 0.1821(4) 0.2339(2) 0.0233(9) Uani 1 1 d . . . H23 H 0.9542 0.1363 0.2694 0.028 Uiso 1 1 calc R . . C24 C 0.9116(3) 0.3340(4) 0.2162(2) 0.0196(8) Uani 1 1 d . . . C25 C 0.8405(2) 0.4042(4) 0.1648(2) 0.0161(8) Uani 1 1 d . . . C26 C 0.9320(3) 0.2696(5) 0.4582(2) 0.0273(9) Uani 1 1 d . . . H26 H 0.9989 0.2727 0.4658 0.033 Uiso 1 1 calc R . . C27 C 0.8853(3) 0.1488(5) 0.4871(2) 0.0270(9) Uani 1 1 d . . . H27 H 0.9202 0.0713 0.5153 0.032 Uiso 1 1 calc R . . C28 C 0.7878(3) 0.1426(5) 0.4743(2) 0.0232(8) Uani 1 1 d . . . H28 H 0.7558 0.0595 0.4925 0.028 Uiso 1 1 calc R . . C29 C 0.7364(2) 0.2587(4) 0.4346(2) 0.0194(8) Uani 1 1 d . . . C30 C 0.7839(3) 0.3794(5) 0.4083(3) 0.0261(9) Uani 1 1 d . . . H30 H 0.7494 0.4601 0.3827 0.031 Uiso 1 1 calc R . . C31 C 0.8821(3) 0.3829(5) 0.4193(3) 0.0301(10) Uani 1 1 d . . . H31 H 0.9144 0.4643 0.3996 0.036 Uiso 1 1 calc R . . C32 C 0.6300(2) 0.2586(4) 0.4274(2) 0.0185(8) Uani 1 1 d . . . H32A H 0.6086 0.3625 0.4331 0.022 Uiso 1 1 calc R . . H32B H 0.6112 0.2007 0.4719 0.022 Uiso 1 1 calc R . . C33 C 0.5994(3) 0.0305(4) 0.3430(2) 0.0203(8) Uani 1 1 d . . . H37A H 0.6681 0.0133 0.3547 0.024 Uiso 1 1 calc R . . H37B H 0.5681 -0.0277 0.3811 0.024 Uiso 1 1 calc R . . C34 C 0.5641(3) -0.0211(5) 0.2597(2) 0.0255(9) Uani 1 1 d . . . H36A H 0.5375 -0.1228 0.2608 0.031 Uiso 1 1 calc R . . H36B H 0.6169 -0.0234 0.2279 0.031 Uiso 1 1 calc R . . C35 C 0.4886(3) 0.0875(5) 0.2237(2) 0.0262(9) Uani 1 1 d . . . H35 H 0.4532 0.0455 0.1743 0.031 Uiso 1 1 calc R . . C36 C 0.5354(3) 0.2357(5) 0.2070(2) 0.0236(9) Uani 1 1 d . . . H34 H 0.5735 0.2172 0.1633 0.028 Uiso 1 1 calc R . . C37 C 0.6054(3) 0.2767(4) 0.2804(2) 0.0193(8) Uani 1 1 d . . . H33A H 0.6701 0.2482 0.2721 0.023 Uiso 1 1 calc R . . H33B H 0.6042 0.3856 0.2893 0.023 Uiso 1 1 calc R . . C38 C 0.4712(2) 0.2200(4) 0.3476(2) 0.0193(8) Uani 1 1 d . . . H38 H 0.4589 0.3233 0.3268 0.023 Uiso 1 1 calc R . . C39 C 0.4224(3) 0.1160(5) 0.2848(2) 0.0242(9) Uani 1 1 d . . . H39A H 0.3631 0.1619 0.2594 0.029 Uiso 1 1 calc R . . H39B H 0.4067 0.0207 0.3091 0.029 Uiso 1 1 calc R . . C40 C 0.4301(2) 0.2139(4) 0.4251(2) 0.0187(8) Uani 1 1 d . . . H40 H 0.4624 0.2894 0.4622 0.022 Uiso 1 1 calc R . . C41 C 0.3269(2) 0.2549(4) 0.4055(2) 0.0194(8) Uani 1 1 d . . . C42 C 0.2584(3) 0.1502(5) 0.4074(2) 0.0232(8) Uani 1 1 d . . . H42 H 0.2743 0.0530 0.4268 0.028 Uiso 1 1 calc R . . C43 C 0.1639(3) 0.1869(4) 0.3807(2) 0.0245(9) Uani 1 1 d . . . H43 H 0.1174 0.1126 0.3840 0.029 Uiso 1 1 calc R . . C44 C 0.2032(2) 0.4272(4) 0.3509(2) 0.0198(8) Uani 1 1 d . . . C45 C 0.2992(3) 0.4018(4) 0.3792(2) 0.0195(8) Uani 1 1 d . . . C46 C 0.3622(3) 0.5239(4) 0.3792(2) 0.0209(8) Uani 1 1 d . . . H46 H 0.4265 0.5110 0.4001 0.025 Uiso 1 1 calc R . . C47 C 0.3319(3) 0.6601(5) 0.3496(3) 0.0264(9) Uani 1 1 d . . . H47 H 0.3754 0.7402 0.3503 0.032 Uiso 1 1 calc R . . C48 C 0.2379(3) 0.6819(4) 0.3185(3) 0.0282(10) Uani 1 1 d . . . H48 H 0.2180 0.7755 0.2963 0.034 Uiso 1 1 calc R . . C49 C 0.1739(3) 0.5685(4) 0.3199(2) 0.0254(9) Uani 1 1 d . . . H49 H 0.1096 0.5847 0.2999 0.030 Uiso 1 1 calc R . . C50 C 0.4639(3) 0.3551(5) 0.1789(3) 0.0302(10) Uani 1 1 d . . . H50 H 0.4052 0.3192 0.1534 0.036 Uiso 1 1 calc R . . C51 C 0.4707(4) 0.4969(6) 0.1844(3) 0.0541(15) Uani 1 1 d . . . H51A H 0.5273 0.5410 0.2092 0.065 Uiso 1 1 calc R . . H51B H 0.4192 0.5581 0.1637 0.065 Uiso 1 1 calc R . . C52 C 0.1753(4) 0.1453(7) 0.1650(3) 0.0543(14) Uani 1 1 d . . . C53 C 0.1500(4) 0.2875(6) 0.1298(3) 0.0458(13) Uani 1 1 d . . . H53A H 0.0823 0.2888 0.1107 0.069 Uiso 1 1 calc R . . H53B H 0.1856 0.3043 0.0856 0.069 Uiso 1 1 calc R . . H53C H 0.1648 0.3664 0.1690 0.069 Uiso 1 1 calc R . . Cl1 Cl 0.58915(6) 0.65415(10) 0.37725(6) 0.0231(2) Uani 1 1 d . . . N1 N 0.5783(2) 0.1956(3) 0.35150(18) 0.0153(6) Uani 1 1 d . . . N2 N 0.1360(2) 0.3174(4) 0.3514(2) 0.0227(7) Uani 1 1 d . . . N3 N 0.1944(4) 0.0343(7) 0.1954(4) 0.097(2) Uani 1 1 d . . . O1 O 0.71574(18) 0.6111(3) 0.24737(16) 0.0222(6) Uani 1 1 d . . . H1 H 0.6774 0.6384 0.2775 0.033 Uiso 1 1 calc R . . O2 O 0.98648(18) 0.4181(3) 0.24650(17) 0.0240(6) Uani 1 1 d . . . H2 H 1.0221 0.3675 0.2793 0.036 Uiso 1 1 calc R . . O3 O 0.69098(18) 0.3724(3) 0.08289(17) 0.0236(6) Uani 1 1 d . . . O4 O 1.02560(17) 0.7372(3) 0.19304(16) 0.0222(6) Uani 1 1 d . . . O6 O 0.44407(18) 0.0706(3) 0.45855(16) 0.0210(6) Uani 1 1 d . . . H6A H 0.4373 0.0743 0.5064 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 C1 0.0230(18) 0.0092(17) 0.018(2) 0.0039(14) 0.0035(15) -0.0008(13) C2 0.032(2) 0.0150(19) 0.020(2) -0.0039(16) 0.0086(17) 0.0011(16) C3 0.033(2) 0.0141(19) 0.026(2) -0.0019(16) 0.0000(18) 0.0010(16) C4 0.026(2) 0.0115(18) 0.030(2) -0.0013(17) -0.0024(18) -0.0007(15) C5 0.0258(19) 0.0115(18) 0.023(2) 0.0025(16) 0.0044(16) 0.0009(15) C6 0.0256(18) 0.0085(17) 0.0194(19) 0.0033(15) 0.0035(15) -0.0004(15) C7 0.0229(19) 0.0119(18) 0.018(2) 0.0006(15) 0.0053(15) -0.0006(14) C8 0.028(2) 0.0131(18) 0.023(2) 0.0017(16) 0.0117(17) -0.0005(15) C9 0.038(2) 0.017(2) 0.027(2) -0.0033(17) 0.0120(19) 0.0018(17) C10 0.044(3) 0.023(2) 0.033(3) -0.0006(19) 0.021(2) -0.0011(19) C11 0.040(3) 0.024(2) 0.043(3) 0.002(2) 0.025(2) 0.0004(19) C12 0.029(2) 0.017(2) 0.043(3) 0.0041(19) 0.0133(19) -0.0006(17) C13 0.029(2) 0.0126(18) 0.030(2) 0.0034(18) 0.0091(17) 0.0030(17) C14 0.0244(19) 0.0141(19) 0.0149(19) 0.0019(14) 0.0053(15) 0.0022(14) C15 0.031(2) 0.0143(19) 0.018(2) 0.0015(16) 0.0011(17) 0.0011(16) C16 0.041(2) 0.018(2) 0.028(3) 0.0061(18) -0.0014(19) 0.0021(18) C17 0.036(2) 0.024(2) 0.028(2) 0.0047(18) -0.0017(19) 0.0064(18) C18 0.034(2) 0.020(2) 0.024(2) 0.0019(17) -0.0006(18) -0.0028(17) C19 0.026(2) 0.0114(18) 0.025(2) 0.0032(16) 0.0023(16) 0.0000(15) C20 0.0205(18) 0.0164(19) 0.018(2) -0.0002(15) 0.0057(15) 0.0019(14) C21 0.0225(18) 0.0141(18) 0.026(2) -0.0030(17) 0.0100(16) -0.0044(16) C22 0.029(2) 0.0080(17) 0.027(2) 0.0002(16) 0.0082(17) -0.0006(15) C23 0.028(2) 0.014(2) 0.028(2) 0.0078(16) 0.0057(17) 0.0033(15) C24 0.0216(19) 0.0118(18) 0.026(2) 0.0000(15) 0.0063(16) -0.0032(14) C25 0.0216(18) 0.0117(18) 0.016(2) -0.0002(14) 0.0075(15) 0.0016(14) C26 0.022(2) 0.036(2) 0.024(2) -0.0066(19) 0.0039(17) -0.0013(18) C27 0.0262(19) 0.027(2) 0.027(2) -0.0023(19) 0.0013(17) 0.0080(18) C28 0.0254(19) 0.021(2) 0.024(2) 0.0010(18) 0.0075(16) -0.0002(17) C29 0.0226(19) 0.0145(18) 0.021(2) -0.0042(16) 0.0044(16) 0.0011(15) C30 0.026(2) 0.023(2) 0.029(2) 0.0032(19) 0.0036(18) -0.0024(16) C31 0.025(2) 0.034(3) 0.031(3) 0.004(2) 0.0066(19) -0.0060(18) C32 0.0224(18) 0.0158(18) 0.018(2) -0.0013(15) 0.0033(15) 0.0010(15) C33 0.028(2) 0.0057(17) 0.027(2) 0.0013(15) 0.0047(17) 0.0046(14) C34 0.033(2) 0.0172(19) 0.027(2) -0.0031(17) 0.0043(18) 0.0036(16) C35 0.028(2) 0.028(2) 0.023(2) -0.0030(18) 0.0073(18) -0.0011(17) C36 0.031(2) 0.022(2) 0.019(2) -0.0004(17) 0.0079(17) 0.0027(17) C37 0.0251(19) 0.0157(19) 0.018(2) 0.0047(15) 0.0074(16) 0.0034(15) C38 0.0223(19) 0.0160(18) 0.021(2) 0.0045(16) 0.0077(16) 0.0037(14) C39 0.028(2) 0.026(2) 0.019(2) 0.0001(17) 0.0033(17) -0.0047(16) C40 0.0226(19) 0.0136(17) 0.020(2) 0.0035(15) 0.0040(16) 0.0023(14) C41 0.0203(18) 0.0185(19) 0.020(2) 0.0013(16) 0.0057(15) 0.0053(15) C42 0.0290(19) 0.0162(18) 0.024(2) 0.0038(18) 0.0037(16) 0.0027(17) C43 0.0223(19) 0.018(2) 0.034(2) 0.0032(17) 0.0059(17) -0.0011(15) C44 0.0207(19) 0.0151(18) 0.024(2) -0.0015(16) 0.0049(16) 0.0000(15) C45 0.0221(19) 0.018(2) 0.019(2) 0.0003(15) 0.0034(16) 0.0021(15) C46 0.0205(18) 0.0155(19) 0.027(2) -0.0024(16) 0.0039(16) 0.0012(15) C47 0.027(2) 0.0154(18) 0.038(2) 0.0002(19) 0.0062(18) -0.0015(17) C48 0.033(2) 0.014(2) 0.036(3) 0.0059(18) -0.0001(19) 0.0013(16) C49 0.026(2) 0.016(2) 0.033(2) 0.0019(17) 0.0005(18) 0.0018(16) C50 0.037(2) 0.029(2) 0.025(2) 0.0039(19) 0.0055(19) 0.0068(19) C51 0.071(4) 0.031(3) 0.053(4) -0.002(3) -0.016(3) 0.006(3) C52 0.058(3) 0.040(3) 0.056(4) 0.006(3) -0.025(3) -0.008(3) C53 0.064(3) 0.036(3) 0.040(3) -0.002(2) 0.012(3) 0.006(2) Cl1 0.0303(5) 0.0153(4) 0.0259(5) -0.0010(4) 0.0117(4) 0.0001(4) N1 0.0229(16) 0.0073(14) 0.0168(16) -0.0006(12) 0.0066(13) 0.0003(11) N2 0.0238(17) 0.0137(16) 0.029(2) -0.0007(14) -0.0009(14) -0.0016(13) N3 0.100(5) 0.047(3) 0.122(6) 0.018(4) -0.063(4) -0.018(3) O1 0.0263(14) 0.0172(13) 0.0252(16) -0.0027(11) 0.0109(12) -0.0026(11) O2 0.0236(14) 0.0126(13) 0.0338(18) 0.0057(12) -0.0034(12) -0.0005(11) O3 0.0271(14) 0.0111(13) 0.0310(17) 0.0040(12) -0.0019(12) -0.0042(10) O4 0.0233(13) 0.0170(14) 0.0274(16) -0.0005(12) 0.0076(12) -0.0028(11) O6 0.0288(14) 0.0161(14) 0.0194(15) 0.0037(11) 0.0077(12) 0.0027(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 C1 O1 1.366(4) . ? C1 C2 1.389(5) . ? C1 C6 1.407(5) . ? C2 C3 1.384(5) . ? C2 H2A 0.9500 . ? C3 C4 1.367(6) . ? C3 H3 0.9500 . ? C4 C5 1.395(6) . ? C4 H4 0.9500 . ? C5 O4 1.373(4) . ? C5 C6 1.393(5) . ? C6 C7 1.519(5) . ? C7 C14 1.518(5) . ? C7 C8 1.533(5) . ? C7 C25 1.544(5) . ? C8 C9 1.389(6) . ? C8 C13 1.392(5) . ? C9 C10 1.386(6) . ? C9 H9 0.9500 . ? C10 C11 1.386(6) . ? C10 H10 0.9500 . ? C11 C12 1.370(6) . ? C11 H11 0.9500 . ? C12 C13 1.384(5) . ? C12 H12 0.9500 . ? C13 O4 1.374(5) . ? C14 C19 1.386(5) . ? C14 C15 1.405(5) . ? C15 C16 1.380(5) . ? C15 H15 0.9500 . ? C16 C17 1.380(6) . ? C16 H16 0.9500 . ? C17 C18 1.382(6) . ? C17 H17 0.9500 . ? C18 C19 1.381(6) . ? C18 H18 0.9500 . ? C19 O3 1.384(4) . ? C20 O3 1.373(5) . ? C20 C25 1.379(5) . ? C20 C21 1.389(5) . ? C21 C22 1.377(6) . ? C21 H21 0.9500 . ? C22 C23 1.373(5) . ? C22 H22 0.9500 . ? C23 C24 1.401(5) . ? C23 H23 0.9500 . ? C24 O2 1.356(4) . ? C24 C25 1.403(5) . ? C26 C31 1.365(6) . ? C26 C27 1.399(6) . ? C26 H26 0.9500 . ? C27 C28 1.385(5) . ? C27 H27 0.9500 . ? C28 C29 1.399(5) . ? C28 H28 0.9500 . ? C29 C30 1.386(5) . ? C29 C32 1.512(5) . ? C30 C31 1.394(6) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C32 N1 1.518(5) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.523(6) . ? C33 N1 1.524(4) . ? C33 H37A 0.9900 . ? C33 H37B 0.9900 . ? C34 C35 1.525(6) . ? C34 H36A 0.9900 . ? C34 H36B 0.9900 . ? C35 C39 1.528(5) . ? C35 C36 1.534(6) . ? C35 H35 1.0000 . ? C36 C50 1.515(6) . ? C36 C37 1.544(6) . ? C36 H34 1.0000 . ? C37 N1 1.515(5) . ? C37 H33A 0.9900 . ? C37 H33B 0.9900 . ? C38 C39 1.522(5) . ? C38 C40 1.526(5) . ? C38 N1 1.542(4) . ? C38 H38 1.0000 . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 O6 1.412(4) . ? C40 C41 1.515(5) . ? C40 H40 1.0000 . ? C41 C42 1.363(5) . ? C41 C45 1.432(5) . ? C42 C43 1.408(5) . ? C42 H42 0.9500 . ? C43 N2 1.316(5) . ? C43 H43 0.9500 . ? C44 N2 1.378(5) . ? C44 C45 1.414(5) . ? C44 C49 1.417(5) . ? C45 C46 1.419(5) . ? C46 C47 1.372(6) . ? C46 H46 0.9500 . ? C47 C48 1.394(5) . ? C47 H47 0.9500 . ? C48 C49 1.372(5) . ? C48 H48 0.9500 . ? C49 H49 0.9500 . ? C50 C51 1.279(7) . ? C50 H50 0.9500 . ? C51 H51A 0.9500 . ? C51 H51B 0.9500 . ? C52 N3 1.141(7) . ? C52 C53 1.437(8) . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? O1 H1 0.8400 . ? O2 H2 0.8400 . ? O6 H6A 0.8400 . ? 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 O1 C1 C2 121.3(3) . . ? O1 C1 C6 116.9(3) . . ? C2 C1 C6 121.8(3) . . ? C3 C2 C1 119.4(3) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C4 C3 C2 121.0(4) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 118.8(4) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? O4 C5 C6 123.2(3) . . ? O4 C5 C4 113.9(3) . . ? C6 C5 C4 122.9(3) . . ? C5 C6 C1 116.1(3) . . ? C5 C6 C7 122.2(3) . . ? C1 C6 C7 121.8(3) . . ? C14 C7 C6 109.4(3) . . ? C14 C7 C8 109.1(3) . . ? C6 C7 C8 109.9(3) . . ? C14 C7 C25 109.2(3) . . ? C6 C7 C25 111.1(3) . . ? C8 C7 C25 108.0(3) . . ? C9 C8 C13 117.1(3) . . ? C9 C8 C7 120.5(3) . . ? C13 C8 C7 122.4(3) . . ? C10 C9 C8 122.0(4) . . ? C10 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? C11 C10 C9 119.1(4) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C12 C11 C10 120.5(4) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 119.6(4) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? O4 C13 C12 115.7(4) . . ? O4 C13 C8 122.6(3) . . ? C12 C13 C8 121.8(4) . . ? C19 C14 C15 116.6(3) . . ? C19 C14 C7 122.9(3) . . ? C15 C14 C7 120.5(3) . . ? C16 C15 C14 121.9(4) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C15 C16 C17 119.4(4) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C16 C17 C18 120.4(4) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 119.2(4) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 O3 115.0(3) . . ? C18 C19 C14 122.4(3) . . ? O3 C19 C14 122.6(3) . . ? O3 C20 C25 122.8(3) . . ? O3 C20 C21 114.6(3) . . ? C25 C20 C21 122.7(4) . . ? C22 C21 C20 119.2(4) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C23 C22 C21 120.4(4) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 119.7(4) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? O2 C24 C23 121.6(4) . . ? O2 C24 C25 117.4(3) . . ? C23 C24 C25 121.0(3) . . ? C20 C25 C24 117.0(3) . . ? C20 C25 C7 122.6(3) . . ? C24 C25 C7 120.3(3) . . ? C31 C26 C27 120.4(4) . . ? C31 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C28 C27 C26 119.7(4) . . ? C28 C27 H27 120.2 . . ? C26 C27 H27 120.2 . . ? C27 C28 C29 120.0(4) . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.0 . . ? C30 C29 C28 119.4(3) . . ? C30 C29 C32 120.5(3) . . ? C28 C29 C32 119.8(3) . . ? C29 C30 C31 120.3(4) . . ? C29 C30 H30 119.9 . . ? C31 C30 H30 119.9 . . ? C26 C31 C30 120.1(4) . . ? C26 C31 H31 119.9 . . ? C30 C31 H31 119.9 . . ? C29 C32 N1 116.1(3) . . ? C29 C32 H32A 108.3 . . ? N1 C32 H32A 108.3 . . ? C29 C32 H32B 108.3 . . ? N1 C32 H32B 108.3 . . ? H32A C32 H32B 107.4 . . ? C34 C33 N1 109.9(3) . . ? C34 C33 H37A 109.7 . . ? N1 C33 H37A 109.7 . . ? C34 C33 H37B 109.7 . . ? N1 C33 H37B 109.7 . . ? H37A C33 H37B 108.2 . . ? C33 C34 C35 108.3(3) . . ? C33 C34 H36A 110.0 . . ? C35 C34 H36A 110.0 . . ? C33 C34 H36B 110.0 . . ? C35 C34 H36B 110.0 . . ? H36A C34 H36B 108.4 . . ? C34 C35 C39 107.5(3) . . ? C34 C35 C36 109.0(3) . . ? C39 C35 C36 108.0(3) . . ? C34 C35 H35 110.7 . . ? C39 C35 H35 110.7 . . ? C36 C35 H35 110.7 . . ? C50 C36 C35 112.2(3) . . ? C50 C36 C37 115.4(3) . . ? C35 C36 C37 107.9(3) . . ? C50 C36 H34 107.0 . . ? C35 C36 H34 107.0 . . ? C37 C36 H34 107.0 . . ? N1 C37 C36 109.5(3) . . ? N1 C37 H33A 109.8 . . ? C36 C37 H33A 109.8 . . ? N1 C37 H33B 109.8 . . ? C36 C37 H33B 109.8 . . ? H33A C37 H33B 108.2 . . ? C39 C38 C40 113.6(3) . . ? C39 C38 N1 107.7(3) . . ? C40 C38 N1 117.1(3) . . ? C39 C38 H38 105.9 . . ? C40 C38 H38 105.9 . . ? N1 C38 H38 105.9 . . ? C38 C39 C35 108.7(3) . . ? C38 C39 H39A 110.0 . . ? C35 C39 H39A 110.0 . . ? C38 C39 H39B 110.0 . . ? C35 C39 H39B 110.0 . . ? H39A C39 H39B 108.3 . . ? O6 C40 C41 113.1(3) . . ? O6 C40 C38 109.7(3) . . ? C41 C40 C38 106.1(3) . . ? O6 C40 H40 109.3 . . ? C41 C40 H40 109.3 . . ? C38 C40 H40 109.3 . . ? C42 C41 C45 118.2(3) . . ? C42 C41 C40 120.7(3) . . ? C45 C41 C40 120.9(3) . . ? C41 C42 C43 119.6(4) . . ? C41 C42 H42 120.2 . . ? C43 C42 H42 120.2 . . ? N2 C43 C42 124.2(4) . . ? N2 C43 H43 117.9 . . ? C42 C43 H43 117.9 . . ? N2 C44 C45 122.1(3) . . ? N2 C44 C49 118.1(3) . . ? C45 C44 C49 119.8(3) . . ? C44 C45 C46 117.7(3) . . ? C44 C45 C41 118.1(3) . . ? C46 C45 C41 124.2(3) . . ? C47 C46 C45 121.3(4) . . ? C47 C46 H46 119.4 . . ? C45 C46 H46 119.4 . . ? C46 C47 C48 120.5(4) . . ? C46 C47 H47 119.7 . . ? C48 C47 H47 119.7 . . ? C49 C48 C47 120.1(4) . . ? C49 C48 H48 119.9 . . ? C47 C48 H48 119.9 . . ? C48 C49 C44 120.5(4) . . ? C48 C49 H49 119.8 . . ? C44 C49 H49 119.8 . . ? C51 C50 C36 129.6(5) . . ? C51 C50 H50 115.2 . . ? C36 C50 H50 115.2 . . ? C50 C51 H51A 120.0 . . ? C50 C51 H51B 120.0 . . ? H51A C51 H51B 120.0 . . ? N3 C52 C53 177.5(8) . . ? C52 C53 H53A 109.5 . . ? C52 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C52 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C37 N1 C32 111.3(3) . . ? C37 N1 C33 108.3(3) . . ? C32 N1 C33 111.3(3) . . ? C37 N1 C38 105.0(3) . . ? C32 N1 C38 110.6(3) . . ? C33 N1 C38 110.1(3) . . ? C43 N2 C44 117.5(3) . . ? C1 O1 H1 109.5 . . ? C24 O2 H2 109.5 . . ? C20 O3 C19 119.2(3) . . ? C5 O4 C13 119.4(3) . . ? C40 O6 H6A 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 O1 C1 C2 C3 179.1(4) . . . . ? C6 C1 C2 C3 0.1(6) . . . . ? C1 C2 C3 C4 -0.2(6) . . . . ? C2 C3 C4 C5 1.4(6) . . . . ? C3 C4 C5 O4 179.3(3) . . . . ? C3 C4 C5 C6 -2.5(6) . . . . ? O4 C5 C6 C1 -179.6(3) . . . . ? C4 C5 C6 C1 2.4(5) . . . . ? O4 C5 C6 C7 2.2(6) . . . . ? C4 C5 C6 C7 -175.8(4) . . . . ? O1 C1 C6 C5 179.8(3) . . . . ? C2 C1 C6 C5 -1.1(5) . . . . ? O1 C1 C6 C7 -2.0(5) . . . . ? C2 C1 C6 C7 177.1(3) . . . . ? C5 C6 C7 C14 -126.3(4) . . . . ? C1 C6 C7 C14 55.6(4) . . . . ? C5 C6 C7 C8 -6.5(5) . . . . ? C1 C6 C7 C8 175.4(3) . . . . ? C5 C6 C7 C25 113.0(4) . . . . ? C1 C6 C7 C25 -65.1(4) . . . . ? C14 C7 C8 C9 -54.3(4) . . . . ? C6 C7 C8 C9 -174.3(3) . . . . ? C25 C7 C8 C9 64.3(5) . . . . ? C14 C7 C8 C13 126.0(4) . . . . ? C6 C7 C8 C13 5.9(5) . . . . ? C25 C7 C8 C13 -115.4(4) . . . . ? C13 C8 C9 C10 0.8(6) . . . . ? C7 C8 C9 C10 -178.9(4) . . . . ? C8 C9 C10 C11 0.1(7) . . . . ? C9 C10 C11 C12 -0.3(7) . . . . ? C10 C11 C12 C13 -0.5(6) . . . . ? C11 C12 C13 O4 -179.4(4) . . . . ? C11 C12 C13 C8 1.5(6) . . . . ? C9 C8 C13 O4 179.3(4) . . . . ? C7 C8 C13 O4 -1.0(6) . . . . ? C9 C8 C13 C12 -1.6(6) . . . . ? C7 C8 C13 C12 178.2(4) . . . . ? C6 C7 C14 C19 -126.3(4) . . . . ? C8 C7 C14 C19 113.4(4) . . . . ? C25 C7 C14 C19 -4.5(5) . . . . ? C6 C7 C14 C15 52.1(4) . . . . ? C8 C7 C14 C15 -68.2(4) . . . . ? C25 C7 C14 C15 173.9(3) . . . . ? C19 C14 C15 C16 1.9(6) . . . . ? C7 C14 C15 C16 -176.7(3) . . . . ? C14 C15 C16 C17 -0.2(6) . . . . ? C15 C16 C17 C18 -1.1(7) . . . . ? C16 C17 C18 C19 0.6(7) . . . . ? C17 C18 C19 O3 -179.7(4) . . . . ? C17 C18 C19 C14 1.2(6) . . . . ? C15 C14 C19 C18 -2.4(6) . . . . ? C7 C14 C19 C18 176.1(4) . . . . ? C15 C14 C19 O3 178.5(4) . . . . ? C7 C14 C19 O3 -2.9(6) . . . . ? O3 C20 C21 C22 -178.0(3) . . . . ? C25 C20 C21 C22 2.0(6) . . . . ? C20 C21 C22 C23 -1.3(5) . . . . ? C21 C22 C23 C24 -0.1(6) . . . . ? C22 C23 C24 O2 -177.7(3) . . . . ? C22 C23 C24 C25 0.9(6) . . . . ? O3 C20 C25 C24 178.7(3) . . . . ? C21 C20 C25 C24 -1.2(5) . . . . ? O3 C20 C25 C7 -4.5(5) . . . . ? C21 C20 C25 C7 175.6(3) . . . . ? O2 C24 C25 C20 178.4(3) . . . . ? C23 C24 C25 C20 -0.2(5) . . . . ? O2 C24 C25 C7 1.5(5) . . . . ? C23 C24 C25 C7 -177.1(4) . . . . ? C14 C7 C25 C20 8.1(5) . . . . ? C6 C7 C25 C20 128.9(4) . . . . ? C8 C7 C25 C20 -110.5(4) . . . . ? C14 C7 C25 C24 -175.2(3) . . . . ? C6 C7 C25 C24 -54.4(4) . . . . ? C8 C7 C25 C24 66.2(4) . . . . ? C31 C26 C27 C28 1.5(6) . . . . ? C26 C27 C28 C29 -1.7(6) . . . . ? C27 C28 C29 C30 0.0(6) . . . . ? C27 C28 C29 C32 -174.3(4) . . . . ? C28 C29 C30 C31 1.9(6) . . . . ? C32 C29 C30 C31 176.1(4) . . . . ? C27 C26 C31 C30 0.3(7) . . . . ? C29 C30 C31 C26 -2.1(7) . . . . ? C30 C29 C32 N1 89.5(4) . . . . ? C28 C29 C32 N1 -96.3(4) . . . . ? N1 C33 C34 C35 -21.7(4) . . . . ? C33 C34 C35 C39 -45.7(4) . . . . ? C33 C34 C35 C36 71.2(4) . . . . ? C34 C35 C36 C50 -174.1(3) . . . . ? C39 C35 C36 C50 -57.5(4) . . . . ? C34 C35 C36 C37 -45.9(4) . . . . ? C39 C35 C36 C37 70.6(4) . . . . ? C50 C36 C37 N1 104.8(4) . . . . ? C35 C36 C37 N1 -21.6(4) . . . . ? C40 C38 C39 C35 -159.4(3) . . . . ? N1 C38 C39 C35 -28.0(4) . . . . ? C34 C35 C39 C38 75.6(4) . . . . ? C36 C35 C39 C38 -41.9(4) . . . . ? C39 C38 C40 O6 63.9(4) . . . . ? N1 C38 C40 O6 -62.5(4) . . . . ? C39 C38 C40 C41 -58.5(4) . . . . ? N1 C38 C40 C41 175.0(3) . . . . ? O6 C40 C41 C42 -11.3(5) . . . . ? C38 C40 C41 C42 109.0(4) . . . . ? O6 C40 C41 C45 173.1(3) . . . . ? C38 C40 C41 C45 -66.7(4) . . . . ? C45 C41 C42 C43 2.8(6) . . . . ? C40 C41 C42 C43 -173.0(3) . . . . ? C41 C42 C43 N2 1.6(6) . . . . ? N2 C44 C45 C46 -177.4(4) . . . . ? C49 C44 C45 C46 3.5(5) . . . . ? N2 C44 C45 C41 3.0(6) . . . . ? C49 C44 C45 C41 -176.1(4) . . . . ? C42 C41 C45 C44 -4.9(5) . . . . ? C40 C41 C45 C44 170.9(3) . . . . ? C42 C41 C45 C46 175.6(4) . . . . ? C40 C41 C45 C46 -8.6(6) . . . . ? C44 C45 C46 C47 -2.8(6) . . . . ? C41 C45 C46 C47 176.7(4) . . . . ? C45 C46 C47 C48 -0.1(6) . . . . ? C46 C47 C48 C49 2.4(6) . . . . ? C47 C48 C49 C44 -1.7(6) . . . . ? N2 C44 C49 C48 179.6(4) . . . . ? C45 C44 C49 C48 -1.3(6) . . . . ? C35 C36 C50 C51 153.7(6) . . . . ? C37 C36 C50 C51 29.6(7) . . . . ? C36 C37 N1 C32 -166.8(3) . . . . ? C36 C37 N1 C33 70.5(4) . . . . ? C36 C37 N1 C38 -47.1(4) . . . . ? C29 C32 N1 C37 -56.7(4) . . . . ? C29 C32 N1 C33 64.3(4) . . . . ? C29 C32 N1 C38 -173.0(3) . . . . ? C34 C33 N1 C37 -45.2(4) . . . . ? C34 C33 N1 C32 -168.0(3) . . . . ? C34 C33 N1 C38 69.0(4) . . . . ? C39 C38 N1 C37 76.8(3) . . . . ? C40 C38 N1 C37 -153.9(3) . . . . ? C39 C38 N1 C32 -163.0(3) . . . . ? C40 C38 N1 C32 -33.7(4) . . . . ? C39 C38 N1 C33 -39.6(4) . . . . ? C40 C38 N1 C33 89.8(4) . . . . ? C42 C43 N2 C44 -3.6(6) . . . . ? C45 C44 N2 C43 1.2(6) . . . . ? C49 C44 N2 C43 -179.7(4) . . . . ? C25 C20 O3 C19 -3.8(5) . . . . ? C21 C20 O3 C19 176.1(3) . . . . ? C18 C19 O3 C20 -171.5(3) . . . . ? C14 C19 O3 C20 7.6(6) . . . . ? C6 C5 O4 C13 3.6(5) . . . . ? C4 C5 O4 C13 -178.2(3) . . . . ? C12 C13 O4 C5 176.6(3) . . . . ? C8 C13 O4 C5 -4.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.470 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.080 # Attachment 'wuz1o_new.cif' data_wuz1o _database_code_depnum_ccdc_archive 'CCDC 616447' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration rm _chemical_formula_moiety 'C27 H31 N2 O2, C25 H16 O4, 5(C2 H3 N), 0.764(C2 H3 N), Cl' _chemical_formula_sum 'C63.53 H64.29 Cl N7.76 O6' _chemical_formula_weight 1068.0 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.2512(15) _cell_length_b 19.807(3) _cell_length_c 34.048(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6238.7(17) _cell_formula_units_Z 4 _cell_measurement_temperature 98(2) _cell_measurement_reflns_used 9251 _cell_measurement_theta_min 2.281 _cell_measurement_theta_max 25.820 _exptl_crystal_description brick _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.136 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2258 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 98(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 40270 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_sigmaI/netI 0.0644 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 28.31 _reflns_number_total 14773 _reflns_number_gt 12467 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0788P)^2^+3.6591P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.29(8) _refine_ls_number_reflns 14773 _refine_ls_number_parameters 723 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0670 _refine_ls_wR_factor_ref 0.1690 _refine_ls_wR_factor_gt 0.1627 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.006 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 0.9290(3) 0.10293(13) 0.92387(7) 0.0155(5) Uani 1 1 d . . . C2 C 1.0734(3) 0.09422(14) 0.91432(7) 0.0185(6) Uani 1 1 d . . . H2A H 1.1235 0.1283 0.9002 0.022 Uiso 1 1 calc R . . C3 C 1.1448(3) 0.03555(14) 0.92550(7) 0.0192(6) Uani 1 1 d . . . H3 H 1.2442 0.0299 0.9193 0.023 Uiso 1 1 calc R . . C4 C 1.0728(3) -0.01423(15) 0.94545(8) 0.0218(6) Uani 1 1 d . . . H4 H 1.1216 -0.0544 0.9530 0.026 Uiso 1 1 calc R . . C5 C 0.9263(3) -0.00536(14) 0.95457(7) 0.0196(6) Uani 1 1 d . . . C6 C 0.8508(3) 0.05359(13) 0.94450(7) 0.0163(5) Uani 1 1 d . . . C7 C 0.6934(3) 0.06408(13) 0.95640(7) 0.0157(5) Uani 1 1 d . . . C8 C 0.6366(3) 0.00187(14) 0.97875(7) 0.0187(6) Uani 1 1 d . . . C9 C 0.4940(3) 0.00065(15) 0.99251(8) 0.0218(6) Uani 1 1 d . . . H9 H 0.4339 0.0390 0.9887 0.026 Uiso 1 1 calc R . . C10 C 0.4396(4) -0.05539(16) 1.01149(8) 0.0282(7) Uani 1 1 d . . . H10 H 0.3429 -0.0552 1.0209 0.034 Uiso 1 1 calc R . . C11 C 0.5254(4) -0.11209(16) 1.01692(9) 0.0304(7) Uani 1 1 d . . . H11 H 0.4871 -0.1510 1.0295 0.037 Uiso 1 1 calc R . . C12 C 0.6660(4) -0.11157(16) 1.00395(10) 0.0324(8) Uani 1 1 d . . . H12 H 0.7259 -0.1500 1.0078 0.039 Uiso 1 1 calc R . . C13 C 0.7201(4) -0.05479(15) 0.98523(8) 0.0239(6) Uani 1 1 d . . . C14 C 0.6852(3) 0.12510(13) 0.98421(7) 0.0155(5) Uani 1 1 d . . . C15 C 0.7733(3) 0.12794(14) 1.01730(7) 0.0184(6) Uani 1 1 d . . . H15 H 0.8396 0.0922 1.0221 0.022 Uiso 1 1 calc R . . C16 C 0.7669(4) 0.18132(15) 1.04332(8) 0.0220(6) Uani 1 1 d . . . H16 H 0.8293 0.1826 1.0655 0.026 Uiso 1 1 calc R . . C17 C 0.6686(4) 0.23311(14) 1.03695(8) 0.0231(6) Uani 1 1 d . . . H17 H 0.6617 0.2694 1.0551 0.028 Uiso 1 1 calc R . . C18 C 0.5810(3) 0.23182(14) 1.00414(8) 0.0215(6) Uani 1 1 d . . . H18 H 0.5147 0.2676 0.9995 0.026 Uiso 1 1 calc R . . C19 C 0.5895(3) 0.17842(14) 0.97782(7) 0.0175(5) Uani 1 1 d . . . C20 C 0.5068(3) 0.13218(13) 0.91772(8) 0.0169(5) Uani 1 1 d . . . C21 C 0.4157(3) 0.14360(15) 0.88576(8) 0.0212(6) Uani 1 1 d . . . H21 H 0.3566 0.1827 0.8846 0.025 Uiso 1 1 calc R . . C22 C 0.4136(3) 0.09625(15) 0.85550(8) 0.0210(6) Uani 1 1 d . . . H22 H 0.3533 0.1033 0.8333 0.025 Uiso 1 1 calc R . . C23 C 0.4993(3) 0.03885(15) 0.85768(8) 0.0219(6) Uani 1 1 d . . . H23 H 0.4962 0.0065 0.8371 0.026 Uiso 1 1 calc R . . C24 C 0.5896(3) 0.02829(15) 0.88974(7) 0.0185(6) Uani 1 1 d . . . C25 C 0.5955(3) 0.07658(14) 0.92103(7) 0.0161(5) Uani 1 1 d . . . C26 C -0.3272(4) 0.40655(17) 0.97107(8) 0.0271(7) Uani 1 1 d . . . H26 H -0.3785 0.4005 0.9950 0.033 Uiso 1 1 calc R . . C27 C -0.2216(4) 0.36039(18) 0.96041(9) 0.0293(7) Uani 1 1 d . . . H27 H -0.2015 0.3227 0.9767 0.035 Uiso 1 1 calc R . . C28 C -0.1450(3) 0.36982(16) 0.92541(8) 0.0247(6) Uani 1 1 d . . . H28 H -0.0726 0.3383 0.9179 0.030 Uiso 1 1 calc R . . C29 C -0.1746(3) 0.42533(15) 0.90151(8) 0.0216(6) Uani 1 1 d . . . C30 C -0.2811(4) 0.47061(17) 0.91214(9) 0.0269(7) Uani 1 1 d . . . H30 H -0.3021 0.5082 0.8957 0.032 Uiso 1 1 calc R . . C31 C -0.3585(4) 0.46103(17) 0.94740(8) 0.0276(7) Uani 1 1 d . . . H31 H -0.4320 0.4920 0.9548 0.033 Uiso 1 1 calc R . . C32 C -0.0965(3) 0.43168(16) 0.86245(8) 0.0209(6) Uani 1 1 d . . . H32A H -0.1600 0.4565 0.8440 0.025 Uiso 1 1 calc R . . H32B H -0.0821 0.3858 0.8516 0.025 Uiso 1 1 calc R . . C33 C 0.1476(3) 0.43463(16) 0.89418(8) 0.0238(6) Uani 1 1 d . . . H33A H 0.1515 0.3853 0.8897 0.029 Uiso 1 1 calc R . . H33B H 0.1079 0.4426 0.9208 0.029 Uiso 1 1 calc R . . C34 C 0.2998(4) 0.46455(19) 0.89126(9) 0.0332(8) Uani 1 1 d . . . H34A H 0.3360 0.4758 0.9178 0.040 Uiso 1 1 calc R . . H34B H 0.3662 0.4311 0.8794 0.040 Uiso 1 1 calc R . . C35 C 0.2955(4) 0.52823(17) 0.86598(8) 0.0269(7) Uani 1 1 d . . . H35 H 0.3914 0.5515 0.8671 0.032 Uiso 1 1 calc R . . C36 C 0.1763(4) 0.57598(17) 0.88234(8) 0.0291(7) Uani 1 1 d . . . H36 H 0.1905 0.5800 0.9114 0.035 Uiso 1 1 calc R . . C37 C 0.0294(4) 0.54128(16) 0.87508(8) 0.0260(7) Uani 1 1 d . . . H37A H -0.0302 0.5439 0.8992 0.031 Uiso 1 1 calc R . . H37B H -0.0228 0.5651 0.8538 0.031 Uiso 1 1 calc R . . C38 C 0.1167(3) 0.46814(15) 0.82201(7) 0.0204(6) Uani 1 1 d . . . H38 H 0.0503 0.4952 0.8050 0.024 Uiso 1 1 calc R . . C39 C 0.2632(4) 0.50711(16) 0.82391(8) 0.0258(7) Uani 1 1 d . . . H39A H 0.3420 0.4779 0.8140 0.031 Uiso 1 1 calc R . . H39B H 0.2581 0.5476 0.8069 0.031 Uiso 1 1 calc R . . C40 C 0.1314(3) 0.39818(14) 0.80284(8) 0.0186(6) Uani 1 1 d . . . H40 H 0.0362 0.3745 0.8042 0.022 Uiso 1 1 calc R . . C41 C 0.1732(3) 0.40743(14) 0.75971(8) 0.0189(6) Uani 1 1 d . . . C42 C 0.3083(3) 0.39104(15) 0.74679(8) 0.0221(6) Uani 1 1 d . . . H42 H 0.3763 0.3716 0.7644 0.026 Uiso 1 1 calc R . . C43 C 0.3471(4) 0.40285(15) 0.70754(8) 0.0230(6) Uani 1 1 d . . . H43 H 0.4418 0.3907 0.6995 0.028 Uiso 1 1 calc R . . C44 C 0.1217(3) 0.44565(14) 0.69294(7) 0.0204(6) Uani 1 1 d . . . C45 C 0.0718(3) 0.43481(14) 0.73207(7) 0.0197(6) Uani 1 1 d . . . C46 C -0.0739(3) 0.45044(14) 0.74134(7) 0.0177(5) Uani 1 1 d . . . H46 H -0.1104 0.4408 0.7668 0.021 Uiso 1 1 calc R . . C47 C -0.1628(3) 0.47945(15) 0.71365(8) 0.0212(6) Uani 1 1 d . . . C48 C -0.1101(4) 0.49071(17) 0.67483(8) 0.0282(7) Uani 1 1 d . . . H48 H -0.1718 0.5101 0.6556 0.034 Uiso 1 1 calc R . . C49 C 0.0269(4) 0.47396(17) 0.66528(8) 0.0263(7) Uani 1 1 d . . . H49 H 0.0599 0.4815 0.6392 0.032 Uiso 1 1 calc R . . C50 C 0.1783(4) 0.64525(17) 0.86531(9) 0.0332(8) Uani 1 1 d . . . H50 H 0.1577 0.6502 0.8381 0.040 Uiso 1 1 calc R . . C51 C 0.2068(5) 0.6995(2) 0.88561(11) 0.0459(10) Uani 1 1 d . . . H51A H 0.2278 0.6961 0.9128 0.055 Uiso 1 1 calc R . . H51B H 0.2065 0.7424 0.8731 0.055 Uiso 1 1 calc R . . C52 C -0.3592(4) 0.49348(19) 0.75843(9) 0.0303(7) Uani 1 1 d . . . H52A H -0.3623 0.4457 0.7659 0.046 Uiso 1 1 calc R . . H52B H -0.4571 0.5123 0.7591 0.046 Uiso 1 1 calc R . . H52C H -0.2974 0.5182 0.7769 0.046 Uiso 1 1 calc R . . C53 C 0.6190(10) 0.6869(3) 0.9897(2) 0.100(2) Uani 1 1 d . . . C54 C 0.5481(12) 0.6575(4) 0.9572(2) 0.129(4) Uani 1 1 d . . . H54A H 0.6145 0.6558 0.9348 0.194 Uiso 1 1 calc R . . H54B H 0.4633 0.6846 0.9502 0.194 Uiso 1 1 calc R . . H54C H 0.5173 0.6116 0.9640 0.194 Uiso 1 1 calc R . . C55 C 0.9104(5) 0.63929(18) 0.75644(10) 0.0385(9) Uani 1 1 d . . . C56 C 0.8018(5) 0.6796(2) 0.73599(11) 0.0462(10) Uani 1 1 d . . . H56A H 0.8256 0.6817 0.7080 0.069 Uiso 1 1 calc R . . H56B H 0.8005 0.7254 0.7469 0.069 Uiso 1 1 calc R . . H56C H 0.7065 0.6588 0.7393 0.069 Uiso 1 1 calc R . . C57 C 0.3264(5) 0.6368(2) 0.71675(11) 0.0509(11) Uani 1 1 d . . . C58 C 0.2203(5) 0.6363(2) 0.68479(11) 0.0444(10) Uani 1 1 d . . . H58A H 0.2684 0.6241 0.6601 0.067 Uiso 1 1 calc R . . H58B H 0.1770 0.6812 0.6822 0.067 Uiso 1 1 calc R . . H58C H 0.1445 0.6032 0.6906 0.067 Uiso 1 1 calc R . . C59 C 0.5611(6) 0.3013(2) 0.87234(12) 0.0557(12) Uani 1 1 d . . . H59A H 0.4585 0.2927 0.8672 0.084 Uiso 1 1 calc R . . H59B H 0.5704 0.3359 0.8928 0.084 Uiso 1 1 calc R . . H59C H 0.6076 0.2595 0.8812 0.084 Uiso 1 1 calc R . . C60 C 0.6298(4) 0.32459(18) 0.83682(11) 0.0365(8) Uani 1 1 d . . . C61 C 0.6290(4) 0.6484(2) 0.83556(10) 0.0401(9) Uani 1 1 d . . . C62 C 0.5666(7) 0.7112(3) 0.82368(14) 0.0684(15) Uani 1 1 d . . . H62A H 0.6437 0.7432 0.8172 0.103 Uiso 1 1 calc R . . H62B H 0.5077 0.7294 0.8451 0.103 Uiso 1 1 calc R . . H62C H 0.5056 0.7039 0.8005 0.103 Uiso 1 1 calc R . . C63 C 0.8557(18) 0.7810(11) 0.9101(3) 0.157(7) Uani 0.764(9) 1 d P . . C64 C 0.9260(8) 0.8298(3) 0.89883(19) 0.0515(17) Uani 0.764(9) 1 d P . . H64A H 0.9382 0.8274 0.8703 0.077 Uiso 0.764(9) 1 calc PR . . H64B H 1.0211 0.8295 0.9115 0.077 Uiso 0.764(9) 1 calc PR . . H64C H 0.8749 0.8715 0.9057 0.077 Uiso 0.764(9) 1 calc PR . . Cl1 Cl 0.04879(9) 0.25015(4) 0.85824(2) 0.02882(17) Uani 1 1 d . . . N1 N 0.0506(3) 0.46742(13) 0.86366(6) 0.0211(5) Uani 1 1 d . . . N2 N 0.2601(3) 0.42977(12) 0.68118(7) 0.0212(5) Uani 1 1 d . . . N3 N 0.6781(9) 0.7113(3) 1.01792(18) 0.109(2) Uani 1 1 d . . . N4 N 0.9964(5) 0.60823(17) 0.77224(10) 0.0514(10) Uani 1 1 d . . . N5 N 0.4087(5) 0.6368(3) 0.74069(12) 0.0827(16) Uani 1 1 d . . . N6 N 0.6834(5) 0.3432(2) 0.80892(10) 0.0631(11) Uani 1 1 d . . . N7 N 0.6770(5) 0.5976(2) 0.84434(14) 0.0712(12) Uani 1 1 d . . . N8 N 0.780(2) 0.7249(14) 0.9165(6) 0.319(16) Uani 0.764(9) 1 d P . . O1 O 0.8558(2) 0.16033(10) 0.91394(6) 0.0205(4) Uani 1 1 d . . . H1 H 0.9119 0.1870 0.9023 0.031 Uiso 1 1 calc R . . O2 O 0.6732(2) -0.02739(10) 0.89266(5) 0.0213(4) Uani 1 1 d . . . H2 H 0.6803 -0.0458 0.8705 0.032 Uiso 1 1 calc R . . O3 O 0.5005(2) 0.18231(10) 0.94586(6) 0.0222(4) Uani 1 1 d . . . O4 O 0.8643(3) -0.05871(10) 0.97400(6) 0.0296(5) Uani 1 1 d . . . O5 O -0.3017(2) 0.49965(13) 0.71954(6) 0.0307(5) Uani 1 1 d . . . O6 O 0.2376(2) 0.35844(11) 0.82260(6) 0.0243(5) Uani 1 1 d . . . H6 H 0.1983 0.3238 0.8320 0.037 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 0.0198(14) 0.0191(13) 0.0077(10) -0.0019(9) -0.0006(10) 0.0021(11) C2 0.0197(14) 0.0245(14) 0.0112(11) -0.0022(10) 0.0018(10) -0.0088(11) C3 0.0151(14) 0.0260(14) 0.0165(12) -0.0052(10) -0.0010(10) -0.0001(11) C4 0.0252(16) 0.0225(14) 0.0177(12) -0.0009(10) -0.0024(11) 0.0043(12) C5 0.0232(15) 0.0214(13) 0.0141(11) 0.0013(10) 0.0025(11) 0.0032(12) C6 0.0204(14) 0.0183(13) 0.0102(10) -0.0047(9) 0.0000(10) -0.0010(11) C7 0.0216(14) 0.0161(13) 0.0092(10) -0.0002(9) -0.0008(10) -0.0003(11) C8 0.0267(15) 0.0201(13) 0.0093(10) -0.0010(10) 0.0014(10) -0.0044(12) C9 0.0289(16) 0.0204(14) 0.0160(12) -0.0027(10) 0.0034(11) -0.0018(12) C10 0.0347(18) 0.0314(16) 0.0184(13) -0.0015(11) 0.0097(13) -0.0074(14) C11 0.046(2) 0.0225(15) 0.0232(14) 0.0053(12) 0.0096(14) -0.0054(14) C12 0.041(2) 0.0232(16) 0.0327(16) 0.0067(13) 0.0144(15) 0.0020(14) C13 0.0320(17) 0.0198(14) 0.0199(13) 0.0020(11) 0.0087(12) 0.0017(12) C14 0.0174(13) 0.0179(13) 0.0111(11) 0.0006(9) 0.0054(10) -0.0013(10) C15 0.0186(14) 0.0214(14) 0.0151(12) 0.0004(10) 0.0035(10) -0.0023(11) C16 0.0280(16) 0.0248(15) 0.0131(12) -0.0001(10) 0.0032(11) -0.0059(12) C17 0.0367(18) 0.0183(14) 0.0145(12) -0.0055(10) 0.0069(12) -0.0026(12) C18 0.0250(16) 0.0159(13) 0.0237(13) -0.0016(10) 0.0070(12) 0.0011(11) C19 0.0188(14) 0.0199(13) 0.0138(11) 0.0014(10) 0.0028(10) -0.0027(11) C20 0.0174(14) 0.0180(13) 0.0152(11) -0.0015(10) 0.0027(10) -0.0054(11) C21 0.0166(14) 0.0232(14) 0.0238(13) 0.0082(11) 0.0017(11) 0.0017(11) C22 0.0183(14) 0.0291(15) 0.0155(11) 0.0040(11) -0.0035(11) -0.0076(12) C23 0.0235(15) 0.0305(15) 0.0118(11) -0.0004(11) 0.0018(11) -0.0074(12) C24 0.0187(14) 0.0258(14) 0.0112(11) -0.0021(10) 0.0043(10) -0.0065(11) C25 0.0177(14) 0.0206(13) 0.0098(10) 0.0001(9) 0.0028(10) -0.0030(11) C26 0.0197(15) 0.0445(19) 0.0173(13) -0.0019(12) 0.0011(12) -0.0061(14) C27 0.0275(17) 0.0365(18) 0.0239(14) 0.0089(13) 0.0005(13) -0.0067(14) C28 0.0189(15) 0.0314(16) 0.0239(14) 0.0026(12) 0.0045(12) -0.0005(13) C29 0.0204(15) 0.0272(15) 0.0172(12) 0.0005(11) -0.0011(11) -0.0037(12) C30 0.0260(17) 0.0310(17) 0.0237(14) -0.0015(12) -0.0005(12) -0.0055(13) C31 0.0203(16) 0.0388(18) 0.0237(14) -0.0082(13) 0.0029(12) -0.0005(14) C32 0.0182(14) 0.0308(15) 0.0139(11) 0.0037(11) -0.0015(11) -0.0067(12) C33 0.0247(16) 0.0331(16) 0.0135(12) 0.0074(11) -0.0057(11) -0.0038(13) C34 0.0282(18) 0.045(2) 0.0260(15) 0.0121(14) -0.0100(13) -0.0092(15) C35 0.0261(17) 0.0354(17) 0.0193(13) 0.0040(12) -0.0072(12) -0.0125(13) C36 0.0366(19) 0.0354(17) 0.0152(12) -0.0011(12) -0.0043(13) -0.0119(15) C37 0.0331(18) 0.0284(15) 0.0166(12) 0.0003(11) -0.0013(12) -0.0050(14) C38 0.0203(15) 0.0295(15) 0.0112(11) 0.0072(11) -0.0015(10) -0.0024(12) C39 0.0278(17) 0.0302(16) 0.0192(13) 0.0083(12) -0.0013(12) -0.0082(13) C40 0.0165(14) 0.0225(14) 0.0169(12) 0.0059(10) -0.0010(10) -0.0047(11) C41 0.0238(15) 0.0176(13) 0.0153(12) 0.0020(10) 0.0005(11) -0.0034(11) C42 0.0220(15) 0.0262(15) 0.0180(13) 0.0092(11) -0.0071(11) -0.0015(12) C43 0.0230(16) 0.0273(15) 0.0185(13) 0.0045(11) 0.0032(12) 0.0012(12) C44 0.0238(15) 0.0243(14) 0.0130(11) 0.0006(10) 0.0010(11) -0.0005(12) C45 0.0255(16) 0.0214(14) 0.0123(11) 0.0034(10) -0.0018(11) -0.0040(12) C46 0.0204(14) 0.0229(14) 0.0098(10) 0.0019(9) 0.0009(10) -0.0021(11) C47 0.0183(15) 0.0287(15) 0.0167(12) 0.0019(11) -0.0051(11) 0.0023(12) C48 0.0289(17) 0.0417(18) 0.0141(12) 0.0051(12) -0.0016(12) 0.0103(14) C49 0.0269(17) 0.0393(17) 0.0128(11) 0.0063(12) 0.0032(11) 0.0021(14) C50 0.041(2) 0.0336(17) 0.0247(15) 0.0003(13) 0.0018(14) -0.0127(15) C51 0.061(3) 0.039(2) 0.0374(19) 0.0037(16) 0.0005(19) -0.0130(19) C52 0.0219(16) 0.0465(19) 0.0227(14) 0.0020(13) 0.0034(12) 0.0062(15) C53 0.143(7) 0.060(4) 0.095(5) 0.025(3) -0.036(5) 0.003(4) C54 0.190(10) 0.100(5) 0.097(5) 0.035(4) -0.056(6) -0.062(6) C55 0.057(3) 0.0311(18) 0.0271(16) 0.0010(14) -0.0016(16) -0.0111(18) C56 0.042(2) 0.061(3) 0.0351(19) 0.0065(18) -0.0111(17) -0.007(2) C57 0.050(3) 0.068(3) 0.0347(19) -0.0084(19) -0.0015(19) 0.031(2) C58 0.042(2) 0.057(2) 0.0342(18) -0.0088(17) -0.0069(16) 0.0232(19) C59 0.070(3) 0.055(3) 0.042(2) 0.0079(19) -0.001(2) -0.029(2) C60 0.041(2) 0.0311(18) 0.0371(18) 0.0067(14) -0.0070(16) -0.0109(16) C61 0.039(2) 0.049(2) 0.0320(17) 0.0025(16) 0.0061(16) -0.0067(18) C62 0.079(4) 0.071(3) 0.055(3) 0.012(2) 0.014(3) 0.036(3) C63 0.138(12) 0.28(2) 0.050(5) -0.006(8) 0.000(6) 0.086(13) C64 0.060(4) 0.043(3) 0.052(3) 0.000(3) 0.006(3) 0.000(3) Cl1 0.0409(5) 0.0236(3) 0.0219(3) 0.0034(3) 0.0077(3) -0.0075(3) N1 0.0205(13) 0.0305(13) 0.0125(9) 0.0068(9) -0.0048(9) -0.0068(11) N2 0.0217(13) 0.0233(12) 0.0186(11) 0.0027(9) 0.0016(10) -0.0012(10) N3 0.169(7) 0.063(3) 0.094(4) 0.010(3) -0.023(4) 0.025(4) N4 0.080(3) 0.0349(17) 0.0389(17) 0.0018(14) -0.0155(18) 0.0026(18) N5 0.070(3) 0.137(4) 0.042(2) -0.019(2) -0.013(2) 0.049(3) N6 0.076(3) 0.075(3) 0.0387(19) 0.0085(18) -0.0052(19) -0.022(2) N7 0.073(3) 0.049(2) 0.092(3) 0.032(2) -0.001(3) 0.010(2) N8 0.27(2) 0.46(3) 0.232(19) 0.08(2) 0.052(16) -0.20(2) O1 0.0218(11) 0.0187(10) 0.0211(9) 0.0083(8) 0.0036(8) 0.0005(8) O2 0.0301(12) 0.0219(10) 0.0121(8) -0.0057(7) 0.0003(8) 0.0032(9) O3 0.0239(11) 0.0199(10) 0.0228(10) -0.0048(8) -0.0059(8) 0.0047(8) O4 0.0329(13) 0.0228(11) 0.0332(11) 0.0093(9) 0.0141(10) 0.0072(10) O5 0.0243(12) 0.0513(14) 0.0166(9) 0.0041(9) -0.0014(9) 0.0115(11) O6 0.0235(11) 0.0274(11) 0.0221(10) 0.0136(9) -0.0020(8) 0.0003(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.366(3) . ? C1 C2 1.385(4) . ? C1 C6 1.405(4) . ? C2 C3 1.390(4) . ? C2 H2A 0.9500 . ? C3 C4 1.370(4) . ? C3 H3 0.9500 . ? C4 C5 1.401(4) . ? C4 H4 0.9500 . ? C5 O4 1.373(3) . ? C5 C6 1.403(4) . ? C6 C7 1.525(4) . ? C7 C25 1.527(4) . ? C7 C14 1.537(4) . ? C7 C8 1.540(4) . ? C8 C13 1.380(4) . ? C8 C9 1.400(4) . ? C9 C10 1.380(4) . ? C9 H9 0.9500 . ? C10 C11 1.387(5) . ? C10 H10 0.9500 . ? C11 C12 1.374(5) . ? C11 H11 0.9500 . ? C12 C13 1.386(4) . ? C12 H12 0.9500 . ? C13 O4 1.390(4) . ? C14 C15 1.392(4) . ? C14 C19 1.395(4) . ? C15 C16 1.381(4) . ? C15 H15 0.9500 . ? C16 C17 1.387(4) . ? C16 H16 0.9500 . ? C17 C18 1.381(4) . ? C17 H17 0.9500 . ? C18 C19 1.388(4) . ? C18 H18 0.9500 . ? C19 O3 1.367(3) . ? C20 C25 1.378(4) . ? C20 O3 1.381(3) . ? C20 C21 1.395(4) . ? C21 C22 1.393(4) . ? C21 H21 0.9500 . ? C22 C23 1.388(4) . ? C22 H22 0.9500 . ? C23 C24 1.390(4) . ? C23 H23 0.9500 . ? C24 O2 1.350(4) . ? C24 C25 1.433(4) . ? C26 C31 1.378(5) . ? C26 C27 1.386(5) . ? C26 H26 0.9500 . ? C27 C28 1.399(4) . ? C27 H27 0.9500 . ? C28 C29 1.395(4) . ? C28 H28 0.9500 . ? C29 C30 1.380(5) . ? C29 C32 1.519(4) . ? C30 C31 1.411(4) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C32 N1 1.535(4) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 N1 1.519(4) . ? C33 C34 1.531(5) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.528(4) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C39 1.522(4) . ? C35 C36 1.555(5) . ? C35 H35 1.0000 . ? C36 C50 1.489(5) . ? C36 C37 1.543(5) . ? C36 H36 1.0000 . ? C37 N1 1.527(4) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 C40 1.538(4) . ? C38 N1 1.544(3) . ? C38 C39 1.561(4) . ? C38 H38 1.0000 . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 O6 1.427(3) . ? C40 C41 1.530(4) . ? C40 H40 1.0000 . ? C41 C42 1.364(4) . ? C41 C45 1.435(4) . ? C42 C43 1.403(4) . ? C42 H42 0.9500 . ? C43 N2 1.318(4) . ? C43 H43 0.9500 . ? C44 N2 1.378(4) . ? C44 C49 1.404(4) . ? C44 C45 1.426(4) . ? C45 C46 1.418(4) . ? C46 C47 1.377(4) . ? C46 H46 0.9500 . ? C47 O5 1.360(4) . ? C47 C48 1.426(4) . ? C48 C49 1.350(5) . ? C48 H48 0.9500 . ? C49 H49 0.9500 . ? C50 C51 1.305(5) . ? C50 H50 0.9500 . ? C51 H51A 0.9500 . ? C51 H51B 0.9500 . ? C52 O5 1.432(4) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 N3 1.206(9) . ? C53 C54 1.414(10) . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? C55 N4 1.141(5) . ? C55 C56 1.460(6) . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? C57 N5 1.115(6) . ? C57 C58 1.466(6) . ? C58 H58A 0.9800 . ? C58 H58B 0.9800 . ? C58 H58C 0.9800 . ? C59 C60 1.442(5) . ? C59 H59A 0.9800 . ? C59 H59B 0.9800 . ? C59 H59C 0.9800 . ? C60 N6 1.133(5) . ? C61 N7 1.140(5) . ? C61 C62 1.428(6) . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? C63 C64 1.23(2) . ? C63 N8 1.33(2) . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? O1 H1 0.8400 . ? O2 H2 0.8400 . ? O6 H6 0.8400 . ? 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 O1 C1 C2 121.6(2) . . ? O1 C1 C6 116.6(2) . . ? C2 C1 C6 121.9(3) . . ? C1 C2 C3 119.9(3) . . ? C1 C2 H2A 120.1 . . ? C3 C2 H2A 120.1 . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.3(3) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? O4 C5 C4 114.5(3) . . ? O4 C5 C6 123.4(3) . . ? C4 C5 C6 122.2(3) . . ? C5 C6 C1 116.4(3) . . ? C5 C6 C7 121.6(2) . . ? C1 C6 C7 122.0(2) . . ? C6 C7 C25 112.2(2) . . ? C6 C7 C14 108.5(2) . . ? C25 C7 C14 109.2(2) . . ? C6 C7 C8 110.3(2) . . ? C25 C7 C8 108.5(2) . . ? C14 C7 C8 107.93(19) . . ? C13 C8 C9 117.4(3) . . ? C13 C8 C7 122.6(3) . . ? C9 C8 C7 120.0(3) . . ? C10 C9 C8 121.0(3) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 120.3(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 119.5(3) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 119.7(3) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C8 C13 C12 122.1(3) . . ? C8 C13 O4 122.6(3) . . ? C12 C13 O4 115.3(3) . . ? C15 C14 C19 117.9(2) . . ? C15 C14 C7 120.1(2) . . ? C19 C14 C7 122.0(2) . . ? C16 C15 C14 121.7(3) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C15 C16 C17 119.6(3) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C18 C17 C16 119.8(3) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C17 C18 C19 120.2(3) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? O3 C19 C18 115.9(3) . . ? O3 C19 C14 123.3(2) . . ? C18 C19 C14 120.8(3) . . ? C25 C20 O3 122.9(2) . . ? C25 C20 C21 123.6(3) . . ? O3 C20 C21 113.5(2) . . ? C22 C21 C20 118.4(3) . . ? C22 C21 H21 120.8 . . ? C20 C21 H21 120.8 . . ? C23 C22 C21 120.2(3) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C24 120.6(3) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? O2 C24 C23 121.6(2) . . ? O2 C24 C25 117.9(2) . . ? C23 C24 C25 120.4(3) . . ? C20 C25 C24 116.7(2) . . ? C20 C25 C7 123.2(2) . . ? C24 C25 C7 120.1(2) . . ? C31 C26 C27 120.8(3) . . ? C31 C26 H26 119.6 . . ? C27 C26 H26 119.6 . . ? C26 C27 C28 119.5(3) . . ? C26 C27 H27 120.3 . . ? C28 C27 H27 120.3 . . ? C29 C28 C27 120.2(3) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? C30 C29 C28 120.0(3) . . ? C30 C29 C32 121.0(3) . . ? C28 C29 C32 118.9(3) . . ? C29 C30 C31 119.9(3) . . ? C29 C30 H30 120.1 . . ? C31 C30 H30 120.1 . . ? C26 C31 C30 119.7(3) . . ? C26 C31 H31 120.1 . . ? C30 C31 H31 120.1 . . ? C29 C32 N1 115.9(2) . . ? C29 C32 H32A 108.3 . . ? N1 C32 H32A 108.3 . . ? C29 C32 H32B 108.3 . . ? N1 C32 H32B 108.3 . . ? H32A C32 H32B 107.4 . . ? N1 C33 C34 109.5(2) . . ? N1 C33 H33A 109.8 . . ? C34 C33 H33A 109.8 . . ? N1 C33 H33B 109.8 . . ? C34 C33 H33B 109.8 . . ? H33A C33 H33B 108.2 . . ? C35 C34 C33 109.4(3) . . ? C35 C34 H34A 109.8 . . ? C33 C34 H34A 109.8 . . ? C35 C34 H34B 109.8 . . ? C33 C34 H34B 109.8 . . ? H34A C34 H34B 108.2 . . ? C39 C35 C34 108.0(3) . . ? C39 C35 C36 111.4(3) . . ? C34 C35 C36 108.6(3) . . ? C39 C35 H35 109.6 . . ? C34 C35 H35 109.6 . . ? C36 C35 H35 109.6 . . ? C50 C36 C37 111.0(3) . . ? C50 C36 C35 114.3(3) . . ? C37 C36 C35 107.2(2) . . ? C50 C36 H36 108.0 . . ? C37 C36 H36 108.0 . . ? C35 C36 H36 108.0 . . ? N1 C37 C36 110.7(3) . . ? N1 C37 H37A 109.5 . . ? C36 C37 H37A 109.5 . . ? N1 C37 H37B 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 108.1 . . ? C40 C38 N1 114.6(2) . . ? C40 C38 C39 112.7(2) . . ? N1 C38 C39 108.1(2) . . ? C40 C38 H38 107.0 . . ? N1 C38 H38 107.0 . . ? C39 C38 H38 107.0 . . ? C35 C39 C38 110.2(2) . . ? C35 C39 H39A 109.6 . . ? C38 C39 H39A 109.6 . . ? C35 C39 H39B 109.6 . . ? C38 C39 H39B 109.6 . . ? H39A C39 H39B 108.1 . . ? O6 C40 C41 110.2(2) . . ? O6 C40 C38 111.0(2) . . ? C41 C40 C38 108.8(2) . . ? O6 C40 H40 109.0 . . ? C41 C40 H40 109.0 . . ? C38 C40 H40 109.0 . . ? C42 C41 C45 118.5(2) . . ? C42 C41 C40 120.8(3) . . ? C45 C41 C40 120.6(3) . . ? C41 C42 C43 120.1(3) . . ? C41 C42 H42 120.0 . . ? C43 C42 H42 120.0 . . ? N2 C43 C42 124.1(3) . . ? N2 C43 H43 118.0 . . ? C42 C43 H43 118.0 . . ? N2 C44 C49 118.5(2) . . ? N2 C44 C45 122.6(3) . . ? C49 C44 C45 119.0(3) . . ? C46 C45 C44 118.9(2) . . ? C46 C45 C41 123.9(2) . . ? C44 C45 C41 117.2(3) . . ? C47 C46 C45 120.4(2) . . ? C47 C46 H46 119.8 . . ? C45 C46 H46 119.8 . . ? O5 C47 C46 125.9(3) . . ? O5 C47 C48 114.4(2) . . ? C46 C47 C48 119.7(3) . . ? C49 C48 C47 120.4(3) . . ? C49 C48 H48 119.8 . . ? C47 C48 H48 119.8 . . ? C48 C49 C44 121.6(3) . . ? C48 C49 H49 119.2 . . ? C44 C49 H49 119.2 . . ? C51 C50 C36 123.7(3) . . ? C51 C50 H50 118.1 . . ? C36 C50 H50 118.1 . . ? C50 C51 H51A 120.0 . . ? C50 C51 H51B 120.0 . . ? H51A C51 H51B 120.0 . . ? O5 C52 H52A 109.5 . . ? O5 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? O5 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? N3 C53 C54 178.8(8) . . ? C53 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? N4 C55 C56 179.2(5) . . ? C55 C56 H56A 109.5 . . ? C55 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C55 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? N5 C57 C58 179.0(5) . . ? C57 C58 H58A 109.5 . . ? C57 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C57 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C60 C59 H59A 109.5 . . ? C60 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C60 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? N6 C60 C59 179.6(6) . . ? N7 C61 C62 178.3(5) . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C64 C63 N8 170.9(14) . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C33 N1 C37 108.2(2) . . ? C33 N1 C32 110.2(2) . . ? C37 N1 C32 109.6(2) . . ? C33 N1 C38 113.5(2) . . ? C37 N1 C38 106.0(2) . . ? C32 N1 C38 109.3(2) . . ? C43 N2 C44 117.5(2) . . ? C1 O1 H1 109.5 . . ? C24 O2 H2 109.5 . . ? C19 O3 C20 119.1(2) . . ? C5 O4 C13 119.4(2) . . ? C47 O5 C52 117.5(2) . . ? C40 O6 H6 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 O1 C1 C2 C3 178.9(2) . . . . ? C6 C1 C2 C3 -0.5(4) . . . . ? C1 C2 C3 C4 0.9(4) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C3 C4 C5 O4 179.0(2) . . . . ? C3 C4 C5 C6 -1.1(4) . . . . ? O4 C5 C6 C1 -178.6(2) . . . . ? C4 C5 C6 C1 1.4(4) . . . . ? O4 C5 C6 C7 3.0(4) . . . . ? C4 C5 C6 C7 -176.9(2) . . . . ? O1 C1 C6 C5 179.9(2) . . . . ? C2 C1 C6 C5 -0.7(4) . . . . ? O1 C1 C6 C7 -1.8(3) . . . . ? C2 C1 C6 C7 177.7(2) . . . . ? C5 C6 C7 C25 -122.6(3) . . . . ? C1 C6 C7 C25 59.2(3) . . . . ? C5 C6 C7 C14 116.6(3) . . . . ? C1 C6 C7 C14 -61.6(3) . . . . ? C5 C6 C7 C8 -1.5(3) . . . . ? C1 C6 C7 C8 -179.7(2) . . . . ? C6 C7 C8 C13 -1.7(3) . . . . ? C25 C7 C8 C13 121.6(3) . . . . ? C14 C7 C8 C13 -120.2(3) . . . . ? C6 C7 C8 C9 179.9(2) . . . . ? C25 C7 C8 C9 -56.7(3) . . . . ? C14 C7 C8 C9 61.5(3) . . . . ? C13 C8 C9 C10 -0.5(4) . . . . ? C7 C8 C9 C10 177.9(2) . . . . ? C8 C9 C10 C11 -0.7(4) . . . . ? C9 C10 C11 C12 1.3(5) . . . . ? C10 C11 C12 C13 -0.7(5) . . . . ? C9 C8 C13 C12 1.1(4) . . . . ? C7 C8 C13 C12 -177.3(3) . . . . ? C9 C8 C13 O4 -178.0(3) . . . . ? C7 C8 C13 O4 3.6(4) . . . . ? C11 C12 C13 C8 -0.5(5) . . . . ? C11 C12 C13 O4 178.6(3) . . . . ? C6 C7 C14 C15 -52.6(3) . . . . ? C25 C7 C14 C15 -175.3(2) . . . . ? C8 C7 C14 C15 67.0(3) . . . . ? C6 C7 C14 C19 128.3(3) . . . . ? C25 C7 C14 C19 5.7(3) . . . . ? C8 C7 C14 C19 -112.1(3) . . . . ? C19 C14 C15 C16 0.4(4) . . . . ? C7 C14 C15 C16 -178.7(3) . . . . ? C14 C15 C16 C17 1.1(4) . . . . ? C15 C16 C17 C18 -1.8(4) . . . . ? C16 C17 C18 C19 0.9(4) . . . . ? C17 C18 C19 O3 -178.8(3) . . . . ? C17 C18 C19 C14 0.6(4) . . . . ? C15 C14 C19 O3 178.1(3) . . . . ? C7 C14 C19 O3 -2.8(4) . . . . ? C15 C14 C19 C18 -1.2(4) . . . . ? C7 C14 C19 C18 177.8(3) . . . . ? C25 C20 C21 C22 0.2(4) . . . . ? O3 C20 C21 C22 179.9(2) . . . . ? C20 C21 C22 C23 0.8(4) . . . . ? C21 C22 C23 C24 -0.9(4) . . . . ? C22 C23 C24 O2 179.5(3) . . . . ? C22 C23 C24 C25 0.0(4) . . . . ? O3 C20 C25 C24 179.3(2) . . . . ? C21 C20 C25 C24 -1.0(4) . . . . ? O3 C20 C25 C7 1.2(4) . . . . ? C21 C20 C25 C7 -179.2(3) . . . . ? O2 C24 C25 C20 -178.6(2) . . . . ? C23 C24 C25 C20 0.9(4) . . . . ? O2 C24 C25 C7 -0.4(4) . . . . ? C23 C24 C25 C7 179.1(3) . . . . ? C6 C7 C25 C20 -125.4(3) . . . . ? C14 C7 C25 C20 -5.0(4) . . . . ? C8 C7 C25 C20 112.4(3) . . . . ? C6 C7 C25 C24 56.6(3) . . . . ? C14 C7 C25 C24 177.0(2) . . . . ? C8 C7 C25 C24 -65.6(3) . . . . ? C31 C26 C27 C28 0.8(5) . . . . ? C26 C27 C28 C29 0.1(5) . . . . ? C27 C28 C29 C30 -0.9(5) . . . . ? C27 C28 C29 C32 -176.1(3) . . . . ? C28 C29 C30 C31 0.7(5) . . . . ? C32 C29 C30 C31 175.8(3) . . . . ? C27 C26 C31 C30 -0.9(5) . . . . ? C29 C30 C31 C26 0.1(5) . . . . ? C30 C29 C32 N1 97.6(3) . . . . ? C28 C29 C32 N1 -87.3(3) . . . . ? N1 C33 C34 C35 13.5(4) . . . . ? C33 C34 C35 C39 -68.5(4) . . . . ? C33 C34 C35 C36 52.4(3) . . . . ? C39 C35 C36 C50 -72.1(3) . . . . ? C34 C35 C36 C50 169.1(3) . . . . ? C39 C35 C36 C37 51.5(3) . . . . ? C34 C35 C36 C37 -67.3(3) . . . . ? C50 C36 C37 N1 138.6(3) . . . . ? C35 C36 C37 N1 13.1(3) . . . . ? C34 C35 C39 C38 58.3(3) . . . . ? C36 C35 C39 C38 -60.8(3) . . . . ? C40 C38 C39 C35 -125.0(3) . . . . ? N1 C38 C39 C35 2.7(3) . . . . ? N1 C38 C40 O6 -68.2(3) . . . . ? C39 C38 C40 O6 55.9(3) . . . . ? N1 C38 C40 C41 170.4(2) . . . . ? C39 C38 C40 C41 -65.4(3) . . . . ? O6 C40 C41 C42 -12.6(4) . . . . ? C38 C40 C41 C42 109.2(3) . . . . ? O6 C40 C41 C45 168.6(2) . . . . ? C38 C40 C41 C45 -69.6(3) . . . . ? C45 C41 C42 C43 1.9(4) . . . . ? C40 C41 C42 C43 -176.9(3) . . . . ? C41 C42 C43 N2 0.2(5) . . . . ? N2 C44 C45 C46 -177.8(3) . . . . ? C49 C44 C45 C46 2.6(4) . . . . ? N2 C44 C45 C41 1.2(4) . . . . ? C49 C44 C45 C41 -178.4(3) . . . . ? C42 C41 C45 C46 176.5(3) . . . . ? C40 C41 C45 C46 -4.7(4) . . . . ? C42 C41 C45 C44 -2.5(4) . . . . ? C40 C41 C45 C44 176.3(3) . . . . ? C44 C45 C46 C47 -4.0(4) . . . . ? C41 C45 C46 C47 177.1(3) . . . . ? C45 C46 C47 O5 -176.6(3) . . . . ? C45 C46 C47 C48 3.2(4) . . . . ? O5 C47 C48 C49 178.9(3) . . . . ? C46 C47 C48 C49 -0.9(5) . . . . ? C47 C48 C49 C44 -0.4(5) . . . . ? N2 C44 C49 C48 180.0(3) . . . . ? C45 C44 C49 C48 -0.4(5) . . . . ? C37 C36 C50 C51 123.6(4) . . . . ? C35 C36 C50 C51 -114.9(4) . . . . ? C34 C33 N1 C37 -67.7(3) . . . . ? C34 C33 N1 C32 172.6(3) . . . . ? C34 C33 N1 C38 49.6(3) . . . . ? C36 C37 N1 C33 51.8(3) . . . . ? C36 C37 N1 C32 171.9(2) . . . . ? C36 C37 N1 C38 -70.2(3) . . . . ? C29 C32 N1 C33 53.3(3) . . . . ? C29 C32 N1 C37 -65.5(3) . . . . ? C29 C32 N1 C38 178.7(2) . . . . ? C40 C38 N1 C33 67.9(3) . . . . ? C39 C38 N1 C33 -58.7(3) . . . . ? C40 C38 N1 C37 -173.5(2) . . . . ? C39 C38 N1 C37 59.9(3) . . . . ? C40 C38 N1 C32 -55.5(3) . . . . ? C39 C38 N1 C32 177.9(2) . . . . ? C42 C43 N2 C44 -1.6(4) . . . . ? C49 C44 N2 C43 -179.6(3) . . . . ? C45 C44 N2 C43 0.8(4) . . . . ? C18 C19 O3 C20 177.7(2) . . . . ? C14 C19 O3 C20 -1.7(4) . . . . ? C25 C20 O3 C19 2.5(4) . . . . ? C21 C20 O3 C19 -177.1(2) . . . . ? C4 C5 O4 C13 178.7(2) . . . . ? C6 C5 O4 C13 -1.2(4) . . . . ? C8 C13 O4 C5 -2.1(4) . . . . ? C12 C13 O4 C5 178.7(3) . . . . ? C46 C47 O5 C52 3.3(5) . . . . ? C48 C47 O5 C52 -176.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 1.364 _refine_diff_density_min -0.902 _refine_diff_density_rms 0.078 # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 -0.264 0.182 0.160 160.4 55.7 2 0.264 0.682 0.340 160.5 55.7 3 -0.236 0.818 0.660 160.5 55.7 4 0.236 0.318 0.840 160.5 55.7