# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_publication_text _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef '- 4.cif' _publ_section_title_ ; Uncommon crystal motif of brucine in its diastereomeric salt with (11-oxo-11H-dibenzo[b,f][1,4]thiazepin-10-yl)- acetic acid. A case of possible crystallization-induced dynamic resolution ; _publ_contact_author_name 'Paola Paoli' _publ_contact_author_address ; Dept. of Energy Engineering University of Florence V. S. Marta, 3 - 50139 Florence - ITALY ; _publ_contact_author_email paolapaoli@unifi.it _publ_contact_author_phone '+39 055 4796240' _publ_contact_author_fax '+39 055 4796342' loop_ _publ_author_name _publ_author_address 'Altamura, Maria R.' ;Menarini Ricerche S.p.A. Via dei Sette Santi, 3 50131 Florence ITALY ; 'Guidi, Antonio' ;Menarini Ricerche S.p.A. Via dei Sette Santi, 3 50131 Florence ITALY ; 'Jierry, Loic' ;Menarini Ricerche S.p.A. Via dei Sette Santi, 3 50131 Florence ITALY ; 'Paoli, Paola' ;Dept of Energy Engineering Via S. Marta, 3 50139 Florence University of Florence ITALY ; 'Rossi, Patrizia' ;Dept of Energy Engineering Via S. Marta, 3 50139 Florence University of Florence ITALY ; data_4 _database_code_depnum_ccdc_archive 'CCDC 791397' #TrackingRef '- 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H43 N3 O8 S' _chemical_formula_weight 737.84 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.4100(10) _cell_length_b 13.0330(10) _cell_length_c 15.183(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.112(9) _cell_angle_gamma 90.00 _cell_volume 1813.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298 _cell_measurement_reflns_used 7070 _cell_measurement_theta_min 4.13 _cell_measurement_theta_max 28.47 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur3 4 circles diffractometer' _diffrn_measurement_method 'intensity from \w scans' _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13002 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0921 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 28.47 _reflns_number_total 7070 _reflns_number_gt 4214 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farruggia, 1997)' _computing_publication_material 'PARST97 (Nardelli, 1995)' _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^)+(0.0402P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'difmap geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration rm _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.09(7) _refine_ls_number_reflns 7070 _refine_ls_number_parameters 626 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.0834 _refine_ls_wR_factor_gt 0.0763 _refine_ls_goodness_of_fit_ref 0.840 _refine_ls_restrained_S_all 0.840 _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 S1 S 0.74122(9) 0.52999(6) 0.57700(5) 0.0414(2) Uani 1 1 d . . . O1 O 0.7146(2) 0.27613(15) 0.73934(13) 0.0385(5) Uani 1 1 d . . . O2 O 0.8179(2) 0.09866(14) 0.63013(14) 0.0389(5) Uani 1 1 d . . . O3 O 0.9809(2) 0.08483(15) 0.76122(13) 0.0348(5) Uani 1 1 d . . . N1 N 0.8415(3) 0.30928(17) 0.63299(15) 0.0310(6) Uani 1 1 d . . . C1 C 0.5833(3) 0.3627(2) 0.61056(18) 0.0345(7) Uani 1 1 d . . . C2 C 0.5773(3) 0.4610(2) 0.57310(18) 0.0350(8) Uani 1 1 d . . . C3 C 0.4435(4) 0.5055(3) 0.53445(19) 0.0420(9) Uani 1 1 d . . . C4 C 0.3150(4) 0.4505(3) 0.5301(2) 0.0518(10) Uani 1 1 d . . . C5 C 0.3198(4) 0.3519(3) 0.5642(2) 0.0548(10) Uani 1 1 d . . . C6 C 0.4527(4) 0.3092(3) 0.6049(2) 0.0463(9) Uani 1 1 d . . . C7 C 0.7170(3) 0.3137(2) 0.6655(2) 0.0324(7) Uani 1 1 d . . . C8 C 0.8565(3) 0.3415(2) 0.54579(18) 0.0285(7) Uani 1 1 d . . . C9 C 0.8225(3) 0.4410(2) 0.51550(19) 0.0329(7) Uani 1 1 d . . . C10 C 0.8570(4) 0.4725(2) 0.4343(2) 0.0365(8) Uani 1 1 d . . . C11 C 0.9195(3) 0.4049(3) 0.3845(2) 0.0391(8) Uani 1 1 d . . . C12 C 0.9467(3) 0.3050(3) 0.4127(2) 0.0379(8) Uani 1 1 d . . . C13 C 0.9139(3) 0.2721(3) 0.4935(2) 0.0343(7) Uani 1 1 d . . . C14 C 0.9578(3) 0.2461(2) 0.6882(2) 0.0303(7) Uani 1 1 d . . . C15 C 0.9122(3) 0.1340(2) 0.6920(2) 0.0318(7) Uani 1 1 d . . . O1B O 0.4429(2) -0.32440(14) 0.81029(13) 0.0367(5) Uani 1 1 d . . . O2B O 0.1670(2) 0.27675(13) 0.94601(12) 0.0323(5) Uani 1 1 d . . . O3B O 0.3789(2) 0.36161(14) 0.89001(12) 0.0346(5) Uani 1 1 d . . . O4B O 0.1793(2) -0.10505(14) 0.96244(14) 0.0358(5) Uani 1 1 d . . . N1B N 0.3922(2) -0.06182(16) 0.92412(15) 0.0247(5) Uani 1 1 d . . . N2B N 0.7820(3) -0.04074(17) 0.79130(15) 0.0277(6) Uani 1 1 d . . . C1B C 0.2713(3) 0.1055(2) 0.94558(19) 0.0273(7) Uani 1 1 d . . . C2B C 0.2735(3) 0.2099(2) 0.93112(18) 0.0253(7) Uani 1 1 d . . . C3B C 0.3870(3) 0.2565(2) 0.89840(17) 0.0256(6) Uani 1 1 d . . . C4B C 0.4946(3) 0.1960(2) 0.87614(18) 0.0261(7) Uani 1 1 d . . . C5B C 0.4906(3) 0.0894(2) 0.88775(18) 0.0252(6) Uani 1 1 d . . . C6B C 0.3804(3) 0.0468(2) 0.92306(17) 0.0248(6) Uani 1 1 d . . . C7B C 0.5917(3) 0.0069(2) 0.86841(16) 0.0236(6) Uani 1 1 d . . . C8B C 0.5001(3) -0.0924(2) 0.87196(19) 0.0239(7) Uani 1 1 d . . . C9B C 0.2820(3) -0.1287(2) 0.92935(18) 0.0281(7) Uani 1 1 d . . . C10B C 0.2997(4) -0.2346(2) 0.8918(2) 0.0307(7) Uani 1 1 d . . . C11B C 0.3458(3) -0.2381(2) 0.8013(2) 0.0310(7) Uani 1 1 d . . . C12B C 0.4955(4) -0.3486(3) 0.7314(3) 0.0450(9) Uani 1 1 d . . . C13B C 0.6339(4) -0.2911(2) 0.7321(2) 0.0389(8) Uani 1 1 d . . . C14B C 0.6333(3) -0.1885(2) 0.72210(19) 0.0310(7) Uani 1 1 d . . . C15B C 0.7711(4) -0.1297(2) 0.7273(2) 0.0332(7) Uani 1 1 d . . . C16B C 0.8264(4) -0.0713(2) 0.8888(2) 0.0328(7) Uani 1 1 d . . . C17B C 0.7387(3) -0.0005(2) 0.93629(19) 0.0284(7) Uani 1 1 d . . . C18B C 0.4120(3) -0.1341(2) 0.78259(18) 0.0270(7) Uani 1 1 d . . . C19B C 0.4946(3) -0.1274(2) 0.70581(19) 0.0291(7) Uani 1 1 d . . . C20B C 0.5296(4) -0.0141(2) 0.6958(2) 0.0283(7) Uani 1 1 d . . . C21B C 0.6393(3) 0.0212(2) 0.77856(17) 0.0246(6) Uani 1 1 d . . . C22B C 0.0379(4) 0.2296(3) 0.9631(3) 0.0381(8) Uani 1 1 d . . . C23B C 0.4897(4) 0.4112(2) 0.8545(2) 0.0343(8) Uani 1 1 d . . . O8 O -0.0026(2) -0.34768(17) 0.77773(17) 0.0543(6) Uani 1 1 d . . . C39 C 0.1219(4) -0.4908(3) 0.7326(3) 0.0782(13) Uani 1 1 d . . . H39A H 0.1602 -0.4406 0.6980 0.117 Uiso 1 1 calc R . . H39B H 0.0688 -0.5418 0.6927 0.117 Uiso 1 1 calc R . . H39C H 0.2008 -0.5229 0.7749 0.117 Uiso 1 1 calc R . . C40 C -0.0483(5) -0.5079(3) 0.8404(3) 0.0823(14) Uani 1 1 d . . . H40A H -0.1090 -0.4672 0.8698 0.123 Uiso 1 1 calc R . . H40B H 0.0258 -0.5412 0.8851 0.123 Uiso 1 1 calc R . . H40C H -0.1068 -0.5587 0.8030 0.123 Uiso 1 1 calc R . . C41 C 0.0222(4) -0.4398(3) 0.7827(2) 0.0531(10) Uani 1 1 d . . . H2NB H 0.862(4) 0.007(2) 0.775(2) 0.059(10) Uiso 1 1 d . . . H3 H 0.449(3) 0.5724(19) 0.5095(15) 0.016(7) Uiso 1 1 d . . . H4 H 0.226(3) 0.486(2) 0.5050(19) 0.042(9) Uiso 1 1 d . . . H5 H 0.226(3) 0.316(2) 0.5586(19) 0.046(9) Uiso 1 1 d . . . H6 H 0.458(3) 0.237(2) 0.6302(17) 0.027(8) Uiso 1 1 d . . . H10 H 0.833(3) 0.545(2) 0.4116(17) 0.030(7) Uiso 1 1 d . . . H11 H 0.953(3) 0.427(2) 0.334(2) 0.058(10) Uiso 1 1 d . . . H12 H 0.989(3) 0.256(2) 0.375(2) 0.045(8) Uiso 1 1 d . . . H13 H 0.926(3) 0.207(3) 0.5184(19) 0.045(9) Uiso 1 1 d . . . H14A H 0.980(3) 0.2673(19) 0.7461(18) 0.021(7) Uiso 1 1 d . . . H14B H 1.056(3) 0.260(2) 0.6626(18) 0.045(8) Uiso 1 1 d . . . H1B H 0.193(3) 0.0753(16) 0.9680(14) 0.029(6) Uiso 1 1 d . . . H4B H 0.577(3) 0.2238(17) 0.8518(16) 0.024(7) Uiso 1 1 d . . . H8B H 0.565(3) -0.144(2) 0.9078(16) 0.025(7) Uiso 1 1 d . . . H10A H 0.381(3) -0.268(2) 0.935(2) 0.048(10) Uiso 1 1 d . . . H10B H 0.207(3) -0.273(2) 0.8917(19) 0.056(10) Uiso 1 1 d . . . H11B H 0.259(3) -0.2548(19) 0.7496(17) 0.024(7) Uiso 1 1 d . . . H12A H 0.420(3) -0.334(2) 0.6753(19) 0.035(9) Uiso 1 1 d . . . H12B H 0.511(3) -0.426(2) 0.7341(16) 0.028(7) Uiso 1 1 d . . . H13B H 0.726(3) -0.335(2) 0.7521(19) 0.041(9) Uiso 1 1 d . . . H15A H 0.864(3) -0.173(2) 0.7484(19) 0.042(8) Uiso 1 1 d . . . H15B H 0.766(2) -0.1018(17) 0.6676(17) 0.016(6) Uiso 1 1 d . . . H16A H 0.794(3) -0.1446(19) 0.8890(15) 0.019(6) Uiso 1 1 d . . . H16B H 0.944(3) -0.065(2) 0.9041(19) 0.042(8) Uiso 1 1 d . . . H17B H 0.780(3) 0.063(2) 0.9442(16) 0.021(7) Uiso 1 1 d . . . H17A H 0.728(3) -0.030(2) 1.000(2) 0.044(8) Uiso 1 1 d . . . H18B H 0.326(3) -0.0899(18) 0.7607(16) 0.019(7) Uiso 1 1 d . . . H19B H 0.423(3) -0.152(2) 0.6535(19) 0.040(9) Uiso 1 1 d . . . H20B H 0.566(3) -0.0014(18) 0.6437(17) 0.021(7) Uiso 1 1 d . . . H20A H 0.450(3) 0.030(2) 0.6911(15) 0.018(7) Uiso 1 1 d . . . H21B H 0.669(3) 0.0937(19) 0.7726(16) 0.021(7) Uiso 1 1 d . . . H22A H -0.012(3) 0.182(2) 0.917(2) 0.048(9) Uiso 1 1 d . . . H22B H 0.059(3) 0.193(3) 1.029(3) 0.070(11) Uiso 1 1 d . . . H22C H -0.027(4) 0.291(3) 0.973(2) 0.079(12) Uiso 1 1 d . . . H23A H 0.600(3) 0.3962(18) 0.8953(17) 0.028(7) Uiso 1 1 d . . . H23B H 0.466(3) 0.489(2) 0.8553(16) 0.025(7) Uiso 1 1 d . . . H23C H 0.496(3) 0.391(2) 0.793(2) 0.053(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0515(5) 0.0327(4) 0.0399(5) -0.0030(4) 0.0104(4) 0.0006(4) O1 0.0455(14) 0.0405(12) 0.0319(12) 0.0055(10) 0.0140(11) -0.0018(11) O2 0.0426(13) 0.0360(11) 0.0367(12) -0.0034(10) 0.0059(11) -0.0088(11) O3 0.0321(12) 0.0353(11) 0.0378(12) 0.0070(10) 0.0096(10) 0.0001(10) N1 0.0324(15) 0.0328(13) 0.0297(14) 0.0015(11) 0.0110(12) -0.0041(12) C1 0.0330(19) 0.0440(19) 0.0281(16) -0.0026(16) 0.0106(15) 0.0000(16) C2 0.039(2) 0.0415(19) 0.0248(16) 0.0024(14) 0.0078(15) 0.0049(16) C3 0.053(3) 0.052(2) 0.0221(17) 0.0038(16) 0.0111(17) 0.015(2) C4 0.037(2) 0.090(3) 0.0308(19) 0.004(2) 0.0117(17) 0.020(2) C5 0.035(2) 0.091(3) 0.038(2) 0.011(2) 0.0069(18) -0.003(2) C6 0.040(2) 0.065(2) 0.0349(19) 0.0087(18) 0.0107(17) 0.001(2) C7 0.0360(19) 0.0317(16) 0.0304(17) -0.0031(14) 0.0092(15) -0.0043(15) C8 0.0269(17) 0.0326(18) 0.0265(16) -0.0047(13) 0.0069(14) -0.0074(14) C9 0.0332(18) 0.0327(17) 0.0322(17) -0.0017(14) 0.0061(15) -0.0047(15) C10 0.0344(19) 0.035(2) 0.0380(19) 0.0049(16) 0.0049(16) -0.0070(15) C11 0.0291(19) 0.054(2) 0.0349(19) 0.0086(17) 0.0079(16) -0.0063(17) C12 0.0320(19) 0.051(2) 0.0332(18) -0.0083(17) 0.0127(15) -0.0070(17) C13 0.0304(18) 0.0387(19) 0.0342(18) -0.0001(16) 0.0079(15) -0.0081(16) C14 0.0302(18) 0.0329(18) 0.0272(18) -0.0013(14) 0.0053(16) -0.0010(15) C15 0.0338(19) 0.0327(17) 0.0323(18) -0.0023(15) 0.0149(16) -0.0017(16) O1B 0.0460(13) 0.0291(12) 0.0390(12) 0.0007(9) 0.0179(11) -0.0015(10) O2B 0.0321(12) 0.0244(10) 0.0459(12) -0.0051(9) 0.0203(10) 0.0003(10) O3B 0.0386(12) 0.0252(11) 0.0443(12) -0.0012(10) 0.0186(10) 0.0007(10) O4B 0.0302(12) 0.0343(11) 0.0481(12) -0.0001(10) 0.0198(11) -0.0035(10) N1B 0.0230(13) 0.0225(12) 0.0308(13) 0.0017(10) 0.0103(11) -0.0015(11) N2B 0.0276(14) 0.0266(13) 0.0320(14) 0.0023(11) 0.0134(12) 0.0036(11) C1B 0.0237(17) 0.0285(17) 0.0331(17) 0.0000(13) 0.0133(14) -0.0005(14) C2B 0.0259(17) 0.0233(15) 0.0280(16) -0.0040(13) 0.0087(14) -0.0006(14) C3B 0.0304(16) 0.0220(15) 0.0262(15) 0.0028(13) 0.0103(14) 0.0023(14) C4B 0.0244(17) 0.0313(16) 0.0252(15) -0.0022(13) 0.0107(14) -0.0080(14) C5B 0.0211(16) 0.0285(16) 0.0266(15) -0.0036(13) 0.0070(13) -0.0012(14) C6B 0.0233(16) 0.0252(16) 0.0254(15) 0.0006(13) 0.0041(13) -0.0010(13) C7B 0.0218(15) 0.0278(16) 0.0217(14) 0.0011(12) 0.0060(12) 0.0009(13) C8B 0.0257(16) 0.0227(15) 0.0244(16) 0.0015(13) 0.0077(13) 0.0029(14) C9B 0.0231(16) 0.0303(16) 0.0301(16) 0.0054(14) 0.0043(14) -0.0002(15) C10B 0.0305(18) 0.0269(16) 0.0371(18) 0.0004(15) 0.0127(16) -0.0035(15) C11B 0.0308(17) 0.0279(16) 0.0326(17) -0.0041(15) 0.0038(15) -0.0006(15) C12B 0.067(3) 0.0266(18) 0.048(2) -0.0101(17) 0.028(2) -0.0049(19) C13B 0.051(2) 0.0294(18) 0.0433(19) -0.0028(15) 0.0246(18) 0.0023(17) C14B 0.043(2) 0.0269(16) 0.0278(16) -0.0017(13) 0.0173(15) 0.0019(15) C15B 0.038(2) 0.0296(17) 0.0355(18) 0.0027(15) 0.0161(16) 0.0104(16) C16B 0.0286(19) 0.0356(19) 0.0350(18) 0.0114(14) 0.0088(15) 0.0025(15) C17B 0.0288(18) 0.0274(16) 0.0295(17) 0.0010(14) 0.0077(15) -0.0093(15) C18B 0.0270(17) 0.0277(16) 0.0274(16) 0.0055(13) 0.0083(14) 0.0028(15) C19B 0.0346(18) 0.0266(16) 0.0257(16) -0.0019(14) 0.0057(15) -0.0040(15) C20B 0.0321(19) 0.0265(16) 0.0289(17) 0.0051(13) 0.0127(15) 0.0074(15) C21B 0.0233(16) 0.0204(15) 0.0329(16) 0.0019(13) 0.0122(14) 0.0017(13) C22B 0.0343(19) 0.0348(19) 0.051(2) -0.0077(18) 0.0222(18) -0.0013(17) C23B 0.046(2) 0.0209(17) 0.041(2) 0.0041(15) 0.0209(18) -0.0021(15) O8 0.0498(15) 0.0300(13) 0.0763(17) -0.0042(12) -0.0001(13) -0.0023(12) C39 0.043(2) 0.054(2) 0.132(4) -0.018(3) 0.005(3) 0.002(2) C40 0.136(4) 0.051(2) 0.052(2) 0.004(2) 0.005(3) -0.022(3) C41 0.045(2) 0.040(2) 0.056(2) -0.0033(19) -0.0249(19) -0.0055(18) _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 S1 C9 1.768(3) . ? S1 C2 1.775(3) . ? O1 C7 1.229(3) . ? O2 C15 1.227(3) . ? O3 C15 1.275(3) . ? N1 C7 1.372(3) . ? N1 C8 1.426(3) . ? N1 C14 1.470(4) . ? C1 C2 1.398(4) . ? C1 C6 1.398(4) . ? C1 C7 1.487(4) . ? C2 C3 1.389(4) . ? C3 C4 1.395(5) . ? C4 C5 1.381(5) . ? C5 C6 1.380(5) . ? C8 C13 1.391(4) . ? C8 C9 1.389(4) . ? C9 C10 1.406(4) . ? C10 C11 1.376(4) . ? C11 C12 1.377(4) . ? C12 C13 1.398(4) . ? C14 C15 1.527(4) . ? O1B C12B 1.431(4) . ? O1B C11B 1.435(3) . ? O2B C2B 1.384(3) . ? O2B C22B 1.437(4) . ? O3B C3B 1.376(3) . ? O3B C23B 1.432(3) . ? O4B C9B 1.226(3) . ? N1B C9B 1.370(3) . ? N1B C6B 1.419(3) . ? N1B C8B 1.478(3) . ? N2B C16B 1.498(4) . ? N2B C15B 1.501(4) . ? N2B C21B 1.540(3) . ? C1B C2B 1.379(4) . ? C1B C6B 1.385(4) . ? C2B C3B 1.413(4) . ? C3B C4B 1.385(4) . ? C4B C5B 1.401(4) . ? C5B C6B 1.387(4) . ? C5B C7B 1.509(4) . ? C7B C17B 1.528(4) . ? C7B C21B 1.540(3) . ? C7B C8B 1.562(4) . ? C8B C18B 1.521(4) . ? C9B C10B 1.517(4) . ? C10B C11B 1.534(4) . ? C11B C18B 1.544(4) . ? C12B C13B 1.501(5) . ? C13B C14B 1.346(4) . ? C14B C15B 1.493(4) . ? C14B C19B 1.500(4) . ? C16B C17B 1.524(4) . ? C18B C19B 1.544(4) . ? C19B C20B 1.528(4) . ? C20B C21B 1.505(4) . ? O8 C41 1.222(4) . ? C39 C41 1.492(5) . ? C40 C41 1.503(5) . ? 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 C9 S1 C2 97.30(13) . . ? C7 N1 C8 126.5(2) . . ? C7 N1 C14 113.8(2) . . ? C8 N1 C14 118.5(2) . . ? C2 C1 C6 118.5(3) . . ? C2 C1 C7 124.9(3) . . ? C6 C1 C7 116.2(3) . . ? C3 C2 C1 120.2(3) . . ? C3 C2 S1 120.0(2) . . ? C1 C2 S1 119.7(2) . . ? C2 C3 C4 119.9(3) . . ? C5 C4 C3 120.4(4) . . ? C6 C5 C4 119.5(4) . . ? C5 C6 C1 121.4(4) . . ? O1 C7 N1 120.4(3) . . ? O1 C7 C1 119.6(3) . . ? N1 C7 C1 120.0(2) . . ? C13 C8 C9 120.5(3) . . ? C13 C8 N1 118.1(3) . . ? C9 C8 N1 121.2(2) . . ? C8 C9 C10 118.8(3) . . ? C8 C9 S1 122.2(2) . . ? C10 C9 S1 119.0(2) . . ? C11 C10 C9 120.5(3) . . ? C10 C11 C12 120.4(3) . . ? C11 C12 C13 120.0(3) . . ? C8 C13 C12 119.5(3) . . ? N1 C14 C15 112.2(3) . . ? O2 C15 O3 125.9(3) . . ? O2 C15 C14 119.4(3) . . ? O3 C15 C14 114.7(3) . . ? C12B O1B C11B 115.2(2) . . ? C2B O2B C22B 115.7(2) . . ? C3B O3B C23B 117.0(2) . . ? C9B N1B C6B 125.2(2) . . ? C9B N1B C8B 118.7(2) . . ? C6B N1B C8B 108.9(2) . . ? C16B N2B C15B 113.4(2) . . ? C16B N2B C21B 107.7(2) . . ? C15B N2B C21B 113.2(2) . . ? C2B C1B C6B 117.9(3) . . ? C1B C2B O2B 123.8(2) . . ? C1B C2B C3B 121.3(3) . . ? O2B C2B C3B 114.8(2) . . ? O3B C3B C4B 124.9(2) . . ? O3B C3B C2B 115.5(2) . . ? C4B C3B C2B 119.6(3) . . ? C3B C4B C5B 119.4(3) . . ? C6B C5B C4B 119.3(3) . . ? C6B C5B C7B 110.5(2) . . ? C4B C5B C7B 130.2(3) . . ? C1B C6B C5B 122.4(2) . . ? C1B C6B N1B 127.5(2) . . ? C5B C6B N1B 109.9(2) . . ? C5B C7B C17B 115.3(2) . . ? C5B C7B C21B 114.2(2) . . ? C17B C7B C21B 101.8(2) . . ? C5B C7B C8B 101.9(2) . . ? C17B C7B C8B 110.2(2) . . ? C21B C7B C8B 113.8(2) . . ? N1B C8B C18B 105.8(2) . . ? N1B C8B C7B 104.3(2) . . ? C18B C8B C7B 117.3(2) . . ? O4B C9B N1B 122.8(3) . . ? O4B C9B C10B 123.1(3) . . ? N1B C9B C10B 114.1(2) . . ? C9B C10B C11B 116.2(2) . . ? O1B C11B C10B 103.9(2) . . ? O1B C11B C18B 115.5(2) . . ? C10B C11B C18B 110.2(2) . . ? O1B C12B C13B 110.4(3) . . ? C14B C13B C12B 120.9(3) . . ? C13B C14B C15B 121.5(3) . . ? C13B C14B C19B 121.8(3) . . ? C15B C14B C19B 116.7(3) . . ? C14B C15B N2B 111.2(2) . . ? N2B C16B C17B 104.3(2) . . ? C16B C17B C7B 102.9(2) . . ? C8B C18B C19B 112.8(2) . . ? C8B C18B C11B 108.1(2) . . ? C19B C18B C11B 118.8(2) . . ? C14B C19B C20B 109.3(3) . . ? C14B C19B C18B 114.4(2) . . ? C20B C19B C18B 106.7(2) . . ? C21B C20B C19B 109.6(2) . . ? C20B C21B C7B 114.8(2) . . ? C20B C21B N2B 111.0(2) . . ? C7B C21B N2B 104.2(2) . . ? O8 C41 C39 122.6(4) . . ? O8 C41 C40 120.9(4) . . ? C39 C41 C40 116.5(3) . . ? _diffrn_measured_fraction_theta_max 0.880 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.503 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.045