# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: data_CEFRAQ # 1. SUBMISSION DETAILS _publ_contact_autor ; Dr. R. de Gelder Crystallography Department University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; _publ_contact_author_phone '031 024 3652842' _publ_contact_author_fax '031 024 3553450' _publ_contact_author_email rdg@sci.kun.nl _publ_requested_journal 'Perkin Transactions 2' _publ_requested_coeditor_name ? _publ_contact_letter ; ; #============================================================================== # 3. AUTHOR LIST loop_ _publ_author_name _publ_author_address 'G.J. Kemperman' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'R. de Gelder' ; Department of Inorganic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'F.J. Dommerholt' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'P.C. Raemakers-Franken' ; DSM Research Department of Organic Chemistry and Biotechnology P.O. Box 18 6160 MD Geleen The Netherlands ; 'A.J.H. Klunder' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'B. Zwanenburg' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; #============================================================================== # 4. TEXT _publ_section_title ; Induced Fit Phenomena in Clathrate Structures of Cephalosporins ; _publ_section_abstract ; ; _publ_section_references ; Beurskens, P. T., Beurskens, G., Bosman, W. P., Gelder, R. de, Garc\'ia-Granda, S., Gould, R. O., Isra\"el, R. & Smits, J. M. M. (1996). DIRDIF-96, A computer program system for crystal structure determination by Patterson methods and direct methods applied to difference structure factors. Crystallography Laboratory, University of Nijmegen, The Netherlands. Beurskens, P. T., Beurskens, G., Strumpel, M. & Nordman, C. E. (1987). In Patterson and Pattersons, pp. 356--367. Glusker, J. P., Patterson, B. K. & Rossi, M., Eds. Oxford, England: Clarendon Press. CAD4 EXPRESS Enraf-Nonius diffractometer control software (1994). Release 5.1, Enraf-Nonius Delft, The Netherlands. Grant, D. F. & Gabe, E. J. (1978). J. Appl. Cryst. 11, 114--120. International Tables for X-ray Crystallography (1974). Vol. IV, Birmingham, England: Kynoch Press. Lehman, M. S. & Larsen, F. K. (1974). Acta Cryst. A30, 580--584. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351--359. Sheldrick, G. M. (1997). SHELXL-97, Program for the refinement of crystal structures. University of G\"ottingen, Germany. Smits, J. M. M., Behm, H., Bosman, W. P. & Beurskens, P. T. (1988). J. Crystallogr. Spectrosc. Res. 18, 447--450. Spek, A. L. (1990). Acta Cryst. A46, C-34. Spek, A. L. (1993). PLUTON, A program for plotting molecular and crystal structures. University of Utrecht, The Netherlands. Spek, A. L. (1995). PLATON-93, Program for display and analysis of crystal and molecular structures. University of Utrecht, The Netherlands. ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #============================================================================== _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 2000-01-17 _chemical_name_systematic ; Cephradine/quinoline complex ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H59 N7 O15 S2' _chemical_formula_weight 954.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 23.4127(9) _cell_length_b 7.1091(2) _cell_length_c 14.8060(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.146(3) _cell_angle_gamma 90.00 _cell_volume 2341.79(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 23.029 _cell_measurement_theta_max 52.473 _exptl_crystal_description 'irregular chunk' _exptl_crystal_colour 'colourless, pale purple hue' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1012 _exptl_absorpt_coefficient_mu 1.660 _exptl_absorpt_correction_type experimental #_exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.968 _exptl_absorpt_correction_T_max 1.070 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius CAD4' _diffrn_measurement_method \w/2\q-scan _diffrn_special_details ; \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.44 + 0.18tan\q)\%, range: 0.68\%-1.41\%, aperture (1.34 + 0.12tan\q)mm., range: 1.35-1.66mm. Maximum scan time: 30 sec/reflection. ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_time 6924 _diffrn_standards_decay_% 1.814 _diffrn_reflns_number 2468 _diffrn_reflns_av_R_equivalents 0.0096 _diffrn_reflns_av_sigmaI/netI 0.0091 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 69.88 _reflns_number_total 2402 _reflns_number_gt 2369 _reflns_number_observed 2369 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; CAD4 EXPRESS (Enraf-Nonius, 1994) ; #_computing_cell_refinement #; #CAD4 EXPRESS (Enraf-Nonius, 1994) #; _computing_data_reduction ; local programs (Smits et al., 1988), profile analysis (Lehman & Larsen, 1974, Grant & Gabe, 1978), EMPABS (North et al., 1968) ; _computing_structure_solution ; DIRDIF (Beurskens et al., 1996), PATTY (Beurskens et al., 1987) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLUTON (Spek, 1993), PLATON (Spek, 1990, 1995) ; _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 ; w=1/[\s^2^(Fo^2^)+(0.0672P)^2^+0.6519P] 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 0.0018(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_Flack -0.01(2) _refine_ls_number_reflns 2402 _refine_ls_number_parameters 395 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0332 _refine_ls_R_factor_gt 0.0329 _refine_ls_R_factor_obs 0.0329 _refine_ls_wR_factor_ref 0.0920 _refine_ls_wR_factor_all 0.0920 _refine_ls_wR_factor_gt 0.0915 _refine_ls_wR_factor_obs 0.0915 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_goodness_of_fit_all 1.061 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.014 _refine_ls_shift/esd_max 0.014 _refine_ls_shift/su_mean 0.001 _refine_ls_shift/esd_mean 0.001 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.16987(3) 0.00817(10) 0.67561(4) 0.0506(2) Uani 1 d . . . C2 C 0.09099(13) 0.0715(4) 0.62664(17) 0.0492(6) Uani 1 d . . . H2A H 0.0837(16) 0.196(6) 0.589(3) 0.067(11) Uiso 1 d . . . H2B H 0.0711(14) -0.017(6) 0.575(2) 0.053(8) Uiso 1 d . . . C3 C 0.05532(10) 0.0891(4) 0.69528(16) 0.0417(5) Uani 1 d . . . C4 C 0.07907(9) 0.1131(3) 0.78837(15) 0.0374(5) Uani 1 d . . . N5 N 0.14232(7) 0.1312(3) 0.82787(12) 0.0365(4) Uani 1 d . . . C6 C 0.18446(10) 0.1651(4) 0.77504(16) 0.0387(5) Uani 1 d . . . H6 H 0.1857(12) 0.300(5) 0.7560(19) 0.038(7) Uiso 1 d . . . C7 C 0.23568(10) 0.1044(4) 0.86616(17) 0.0378(5) Uani 1 d . . . H7 H 0.2608(11) 0.203(4) 0.8931(18) 0.028(6) Uiso 1 d . . . C8 C 0.18388(9) 0.0635(3) 0.90688(16) 0.0373(5) Uani 1 d . . . C9 C 0.04471(9) 0.1449(4) 0.85798(16) 0.0445(6) Uani 1 d . . . C10 C -0.01205(13) 0.0870(6) 0.6455(2) 0.0597(7) Uani 1 d . . . H10A H -0.027(2) -0.034(9) 0.620(3) 0.096(15) Uiso 1 d . . . H10B H -0.0232(18) 0.196(7) 0.587(3) 0.074(11) Uiso 1 d . . . H10C H -0.0396(16) 0.140(6) 0.683(2) 0.063(9) Uiso 1 d . . . O11 O -0.00106(8) 0.0467(4) 0.85005(17) 0.0672(7) Uani 1 d . . . O12 O 0.06341(8) 0.2725(4) 0.91763(12) 0.0544(5) Uani 1 d . . . O13 O 0.18041(7) -0.0050(3) 0.97996(11) 0.0481(4) Uani 1 d . . . N14 N 0.27153(8) -0.0565(3) 0.86143(16) 0.0409(4) Uani 1 d . . . H14 H 0.2547(17) -0.170(6) 0.855(3) 0.065(10) Uiso 1 d . . . C15 C 0.32927(9) -0.0379(4) 0.86697(16) 0.0391(5) Uani 1 d . . . O16 O 0.35516(9) 0.1126(3) 0.8768(2) 0.0705(7) Uani 1 d . . . C17 C 0.36143(9) -0.2220(4) 0.86059(16) 0.0393(5) Uani 1 d . . . H17 H 0.3545(11) -0.304(4) 0.9051(19) 0.031(6) Uiso 1 d . . . N18 N 0.42705(9) -0.1808(5) 0.89237(16) 0.0510(6) Uani 1 d . . . H18A H 0.4505(19) -0.297(8) 0.878(3) 0.084(13) Uiso 1 d . . . H18B H 0.4403(14) -0.173(5) 0.961(2) 0.052(8) Uiso 1 d . . . H18C H 0.4347(14) -0.082(5) 0.870(2) 0.043(9) Uiso 1 d . . . C19 C 0.34122(10) -0.3083(4) 0.76217(16) 0.0395(5) Uani 1 d . . . C20 C 0.33847(15) -0.1861(5) 0.67952(19) 0.0549(7) Uani 1 d . . . H20A H 0.375(2) -0.116(9) 0.688(3) 0.098(15) Uiso 1 d . . . H20B H 0.3050(18) -0.069(7) 0.678(3) 0.071(11) Uiso 1 d . . . C21 C 0.32127(17) -0.2916(7) 0.5871(2) 0.0687(9) Uani 1 d . . . H21 H 0.324(2) -0.212(10) 0.537(4) 0.116(18) Uiso 1 d . . . C22 C 0.30796(18) -0.4710(7) 0.5794(3) 0.0761(10) Uani 1 d . . . H22 H 0.2996(18) -0.537(7) 0.519(3) 0.083(12) Uiso 1 d . . . C23 C 0.3089(3) -0.5906(7) 0.6603(3) 0.0871(12) Uani 1 d . . . H23A H 0.340(2) -0.683(10) 0.664(4) 0.105(17) Uiso 1 d . . . H23B H 0.257(3) -0.638(10) 0.648(4) 0.13(2) Uiso 1 d . . . C24 C 0.32751(16) -0.4895(5) 0.7531(2) 0.0608(7) Uani 1 d . . . H24 H 0.3324(18) -0.562(7) 0.805(3) 0.082(13) Uiso 1 d . . . N30 N 0.5276(3) 0.0826(7) 0.6296(3) 0.1092(16) Uani 0.50 d P A 1 C30 C 0.5276(3) 0.0826(7) 0.6296(3) 0.1092(16) Uani 0.50 d P A 2 H30 H 0.5122 0.0826 0.6805 0.131 Uiso 0.50 calc PR A 2 C31 C 0.4903(2) 0.0821(5) 0.5407(2) 0.0715(9) Uani 1 d . . . C32 C 0.4257(3) 0.0832(6) 0.5246(4) 0.1000(14) Uani 1 d . . . H32 H 0.4090 0.0842 0.5739 0.120 Uiso 1 calc R . . C33 C 0.3893(3) 0.0826(7) 0.4248(6) 0.113(2) Uani 1 d . . . H33 H 0.3476 0.0818 0.4087 0.135 Uiso 1 calc R . . C34 C 0.5844(4) 0.0831(7) 0.6448(4) 0.115(2) Uani 1 d . . . H34 H 0.6092 0.0839 0.7076 0.138 Uiso 1 calc R B 1 O40 O 0.28243(11) 0.0886(4) 0.13731(17) 0.0592(5) Uani 1 d . . . H40A H 0.312(3) 0.093(12) 0.110(4) 0.13(2) Uiso 1 d . . . H40B H 0.2575(19) 0.037(7) 0.096(3) 0.067(12) Uiso 1 d . . . O50 O 0.39056(16) 0.1205(7) 0.1072(3) 0.0931(9) Uani 1 d . . . H50A H 0.386(2) 0.028(9) 0.076(4) 0.086(17) Uiso 1 d . . . H50B H 0.410(4) 0.222(18) 0.083(6) 0.19(4) Uiso 1 d . . . O60 O 0.0374(2) 0.6408(8) 0.2122(4) 0.1205(13) Uani 1 d . . . H60A H 0.014(2) 0.668(11) 0.137(5) 0.12(2) Uiso 1 d . . . H60B H 0.061(4) 0.764(17) 0.224(6) 0.18(4) Uiso 1 d . . . O70 O 0.0000 0.717(2) 0.0000 0.303(9) Uani 1 d S . . 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 0.0551(3) 0.0601(4) 0.0425(3) -0.0083(3) 0.0237(2) 0.0098(3) C2 0.0616(14) 0.0458(13) 0.0357(11) -0.0002(11) 0.0089(10) 0.0081(12) C3 0.0403(11) 0.0400(11) 0.0393(11) -0.0020(10) 0.0045(8) 0.0086(10) C4 0.0277(9) 0.0427(12) 0.0406(10) -0.0024(10) 0.0090(8) 0.0091(9) N5 0.0278(8) 0.0496(11) 0.0334(8) -0.0047(8) 0.0116(6) 0.0052(8) C6 0.0383(10) 0.0405(12) 0.0415(11) 0.0002(10) 0.0185(9) 0.0040(10) C7 0.0306(9) 0.0374(11) 0.0467(11) -0.0055(10) 0.0139(8) 0.0037(10) C8 0.0292(9) 0.0436(13) 0.0395(11) -0.0072(9) 0.0113(7) 0.0059(8) C9 0.0285(10) 0.0593(15) 0.0458(11) -0.0016(12) 0.0117(8) 0.0114(10) C10 0.0433(13) 0.0630(17) 0.0561(15) -0.0078(15) -0.0086(11) 0.0075(14) O11 0.0404(9) 0.0842(18) 0.0849(14) -0.0198(13) 0.0312(9) -0.0051(10) O12 0.0457(9) 0.0748(13) 0.0458(9) -0.0133(10) 0.0189(7) 0.0062(10) O13 0.0397(7) 0.0674(11) 0.0384(7) 0.0066(9) 0.0137(6) 0.0091(9) N14 0.0282(8) 0.0376(10) 0.0587(11) -0.0045(9) 0.0163(8) 0.0027(8) C15 0.0327(10) 0.0452(13) 0.0438(11) 0.0034(9) 0.0185(8) 0.0049(10) O16 0.0442(10) 0.0489(12) 0.130(2) 0.0022(13) 0.0432(12) -0.0032(9) C17 0.0320(10) 0.0495(13) 0.0402(10) 0.0086(11) 0.0167(8) 0.0117(10) N18 0.0310(9) 0.0791(19) 0.0431(11) -0.0011(12) 0.0119(8) 0.0131(11) C19 0.0336(10) 0.0474(13) 0.0419(11) 0.0067(10) 0.0182(8) 0.0092(10) C20 0.0664(17) 0.0561(17) 0.0433(12) 0.0075(12) 0.0184(11) -0.0023(14) C21 0.0735(19) 0.089(3) 0.0433(14) 0.0047(16) 0.0172(13) -0.0052(19) C22 0.084(2) 0.086(3) 0.0580(17) -0.0208(19) 0.0216(15) -0.017(2) C23 0.118(4) 0.064(2) 0.087(3) -0.017(2) 0.043(2) -0.016(2) C24 0.0762(18) 0.0518(15) 0.0627(16) 0.0069(15) 0.0338(14) 0.0017(16) N30 0.171(5) 0.0553(19) 0.080(2) 0.0042(19) 0.009(3) 0.006(3) C30 0.171(5) 0.0553(19) 0.080(2) 0.0042(19) 0.009(3) 0.006(3) C31 0.116(3) 0.0368(13) 0.0662(17) 0.0032(14) 0.0349(18) 0.0010(17) C32 0.133(4) 0.0477(18) 0.141(4) 0.015(2) 0.075(3) -0.004(2) C33 0.100(3) 0.0465(18) 0.174(6) 0.014(3) 0.018(4) -0.009(2) C34 0.168(6) 0.057(2) 0.091(3) -0.006(2) -0.001(4) 0.013(4) O40 0.0558(11) 0.0530(11) 0.0640(12) 0.0031(10) 0.0119(10) 0.0072(10) O50 0.0865(19) 0.104(3) 0.098(2) 0.006(2) 0.0416(16) 0.018(2) O60 0.123(3) 0.121(3) 0.138(3) -0.006(3) 0.070(3) 0.014(3) O70 0.47(2) 0.199(13) 0.153(7) 0.000 -0.024(10) 0.000 _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 C6 1.793(2) . Y S1 C2 1.818(3) . Y C2 C3 1.508(4) . Y C3 C4 1.327(3) . Y C3 C10 1.519(3) . Y C4 N5 1.419(2) . Y C4 C9 1.509(3) . Y N5 C8 1.356(3) . Y N5 C6 1.457(3) . Y C6 C7 1.561(3) . Y C7 N14 1.433(3) . Y C7 C8 1.541(3) . Y C8 O13 1.212(3) . Y C9 O12 1.246(3) . Y C9 O11 1.253(3) . Y N14 C15 1.335(3) . Y C15 O16 1.216(3) . Y C15 C17 1.527(3) . Y C17 N18 1.489(3) . Y C17 C19 1.515(3) . Y C19 C24 1.324(5) . Y C19 C20 1.486(4) . Y C20 C21 1.502(5) . Y C21 C22 1.309(6) . Y C22 C23 1.464(7) . Y C23 C24 1.491(6) . Y N30 C34 1.278(9) . Y N30 C31 1.334(6) . Y C31 C31 1.412(7) 2_656 Y C31 C32 1.457(7) . Y C32 C33 1.457(9) . Y C33 C34 1.355(9) 2_656 Y C34 C33 1.355(9) 2_656 Y 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 C6 S1 C2 94.79(11) . . Y C3 C2 S1 117.30(17) . . Y C4 C3 C2 124.7(2) . . Y C4 C3 C10 122.7(2) . . Y C2 C3 C10 112.4(2) . . Y C3 C4 N5 119.07(19) . . Y C3 C4 C9 126.06(19) . . Y N5 C4 C9 114.52(18) . . Y C8 N5 C4 134.4(2) . . Y C8 N5 C6 95.62(16) . . Y C4 N5 C6 126.02(17) . . Y N5 C6 C7 87.53(16) . . Y N5 C6 S1 110.51(16) . . Y C7 C6 S1 115.87(17) . . Y N14 C7 C8 114.4(2) . . Y N14 C7 C6 118.8(2) . . Y C8 C7 C6 84.48(16) . . Y O13 C8 N5 133.1(2) . . Y O13 C8 C7 134.8(2) . . Y N5 C8 C7 92.07(18) . . Y O12 C9 O11 125.0(2) . . Y O12 C9 C4 116.7(2) . . Y O11 C9 C4 118.3(2) . . Y C15 N14 C7 121.0(2) . . Y O16 C15 N14 123.5(2) . . Y O16 C15 C17 121.63(18) . . Y N14 C15 C17 114.9(2) . . Y N18 C17 C19 111.47(18) . . Y N18 C17 C15 107.0(2) . . Y C19 C17 C15 113.22(18) . . Y C24 C19 C20 122.6(3) . . Y C24 C19 C17 119.0(3) . . Y C20 C19 C17 118.4(2) . . Y C19 C20 C21 112.9(3) . . Y C22 C21 C20 123.7(3) . . Y C21 C22 C23 123.5(4) . . Y C22 C23 C24 113.6(4) . . Y C19 C24 C23 123.7(3) . . Y C34 N30 C31 119.9(6) . . Y N30 C31 C31 123.9(6) . 2_656 Y N30 C31 C32 119.2(5) . . Y C31 C31 C32 116.9(5) 2_656 . Y C33 C32 C31 114.5(5) . . Y C34 C33 C32 120.7(6) 2_656 . Y N30 C34 C33 124.1(6) . 2_656 Y _diffrn_reflns_theta_full 69.88 _refine_diff_density_max 0.288 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.036 _publ_section_experimental ; Crystal colour: colourless, pale purple hue, crystal shape: irregular chunk. Profile analysis combining the methods of Lehman & Larsen (1974) and Grant & Gabe (1978). Empirical absorption correction using EMPABS (North, Phillips & Mathews, 1968). Data collection parameters: \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.44 + 0.18tan\q)\%, range: 0.68\%-1.41\%, aperture (1.34 + 0.12tan\q)mm., range: 1.35-1.66mm. Maximum scan time: 30 sec/reflection. Least-squares refinement using calculated weights: w=1/[\s^2^(Fo^2^)+(0.0672P)^2^+0.6519P] where P=(Fo^2^+2Fc^2^)/3 ; #===END data_CEFRAA # 1. SUBMISSION DETAILS _publ_contact_autor ; Dr. R. de Gelder Crystallography Department University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; _publ_contact_author_phone '031 024 3652842' _publ_contact_author_fax '031 024 3553450' _publ_contact_author_email rdg@sci.kun.nl _publ_requested_journal 'Perkin Transactions 2' _publ_requested_coeditor_name ? _publ_contact_letter ; ; #============================================================================== # 3. AUTHOR LIST loop_ _publ_author_name _publ_author_address 'G.J. Kemperman' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'R. de Gelder' ; Department of Inorganic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'F.J. Dommerholt' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'P.C. Raemakers-Franken' ; DSM Research Department of Organic Chemistry and Biotechnology P.O. Box 18 6160 MD Geleen The Netherlands ; 'A.J.H. Klunder' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'B. Zwanenburg' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; #============================================================================== # 4. TEXT _publ_section_title ; Induced Fit Phenomena in Clathrate Structures of Cephalosporins ; _publ_section_abstract ; ; _publ_section_references ; Beurskens, P. T., Beurskens, G., Bosman, W. P., Gelder, R. de, Garc\'ia-Granda, S., Gould, R. O., Isra\"el, R. & Smits, J. M. M. (1996). DIRDIF-96, A computer program system for crystal structure determination by Patterson methods and direct methods applied to difference structure factors. Crystallography Laboratory, University of Nijmegen, The Netherlands. CAD4 EXPRESS Enraf-Nonius diffractometer control software (1994). Release 5.1, Enraf-Nonius Delft, The Netherlands. Grant, D. F. & Gabe, E. J. (1978). J. Appl. Cryst. 11, 114--120. International Tables for X-ray Crystallography (1974). Vol. IV, Birmingham, England: Kynoch Press. Lehman, M. S. & Larsen, F. K. (1974). Acta Cryst. A30, 580--584. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351--359. Sheldrick, G. M. (1997). SHELXL-97, Program for the refinement of crystal structures. University of G\"ottingen, Germany. Smits, J. M. M., Behm, H., Bosman, W. P. & Beurskens, P. T. (1988). J. Crystallogr. Spectrosc. Res. 18, 447--450. Spek, A. L. (1990). Acta Cryst. A46, C-34. Spek, A. L. (1993). PLUTON, A program for plotting molecular and crystal structures. University of Utrecht, The Netherlands. Spek, A. L. (1995). PLATON-93, Program for display and analysis of crystal and molecular structures. University of Utrecht, The Netherlands. ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #============================================================================== _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 1999-05-04 _chemical_name_systematic ; Cephradine/alpha-naphthol complex ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H58 N6 O15 S2' _chemical_formula_weight 951.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 23.471(2) _cell_length_b 7.1215(10) _cell_length_c 14.9304(19) _cell_angle_alpha 90.00 _cell_angle_beta 108.268(14) _cell_angle_gamma 90.00 _cell_volume 2369.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 21 _cell_measurement_theta_min 13.125 _cell_measurement_theta_max 20.888 _exptl_crystal_description 'regular platelet' _exptl_crystal_colour 'transparent light yellow-brown' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 1.633 _exptl_absorpt_correction_type experimental #_exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.976 _exptl_absorpt_correction_T_max 1.024 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius CAD4' _diffrn_measurement_method \w-scan _diffrn_special_details ; \w-scan with fixed scan width and variable scan speed. Scan width 1.80\%, aperture 4.00mm. Maximum scan time: 30 sec/reflection. ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_time 7200 _diffrn_standards_decay_% 6.414 _diffrn_reflns_number 4988 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0861 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.97 _diffrn_reflns_theta_max 69.90 _reflns_number_total 4411 _reflns_number_gt 2413 _reflns_number_observed 2413 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; CAD4 EXPRESS (Enraf-Nonius, 1994) ; #_computing_cell_refinement #; #CAD4 EXPRESS (Enraf-Nonius, 1994) #; _computing_data_reduction ; local programs (Smits et al., 1988), profile analysis (Lehman & Larsen, 1974, Grant & Gabe, 1978), EMPABS (North et al., 1968) ; _computing_structure_solution ; DIRDIF (Beurskens et al., 1996), ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLUTON (Spek, 1993), PLATON (Spek, 1990, 1995) ; _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 ; w=1/[\s^2^(Fo^2^)+(0.0947P)^2^+2.0329P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack 0.03(5) _refine_ls_number_reflns 4411 _refine_ls_number_parameters 299 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1431 _refine_ls_R_factor_gt 0.0756 _refine_ls_R_factor_obs 0.0756 _refine_ls_wR_factor_ref 0.2188 _refine_ls_wR_factor_all 0.2188 _refine_ls_wR_factor_gt 0.1792 _refine_ls_wR_factor_obs 0.1792 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_goodness_of_fit_all 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_shift/esd_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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.17131(8) 0.0682(3) 0.67666(12) 0.0642(5) Uani 1 d . . . C2 C 0.0937(3) 0.1329(11) 0.6288(4) 0.0589(19) Uani 1 d . . . H2A H 0.0919 0.2516 0.5961 0.071 Uiso 1 calc R . . H2B H 0.0742 0.0400 0.5816 0.071 Uiso 1 calc R . . C3 C 0.0568(3) 0.1531(11) 0.6937(4) 0.0523(16) Uani 1 d . . . C4 C 0.0802(2) 0.1808(11) 0.7860(4) 0.0486(16) Uani 1 d . . . N5 N 0.1433(2) 0.1943(8) 0.8268(3) 0.0476(14) Uani 1 d . . . C6 C 0.1859(3) 0.2244(11) 0.7739(5) 0.0511(17) Uani 1 d . . . H6 H 0.1891 0.3560 0.7569 0.061 Uiso 1 calc R . . C7 C 0.2365(3) 0.1618(12) 0.8656(5) 0.0539(17) Uani 1 d . . . H7 H 0.2614 0.2679 0.8971 0.065 Uiso 1 calc R . . C8 C 0.1840(2) 0.1260(11) 0.9047(4) 0.0503(19) Uani 1 d . . . C9 C 0.0453(3) 0.2105(12) 0.8548(5) 0.0555(19) Uani 1 d . . . C10 C -0.0095(3) 0.1509(14) 0.6437(5) 0.076(2) Uani 1 d . . . H10A H -0.0166 0.1282 0.5777 0.113 Uiso 1 calc R . . H10B H -0.0264 0.2700 0.6518 0.113 Uiso 1 calc R . . H10C H -0.0278 0.0533 0.6694 0.113 Uiso 1 calc R . . O11 O -0.0008(2) 0.1191(8) 0.8466(4) 0.0797(19) Uani 1 d . . . O12 O 0.0649(2) 0.3380(8) 0.9150(3) 0.0672(15) Uani 1 d . . . O13 O 0.17966(18) 0.0537(8) 0.9768(3) 0.0602(13) Uani 1 d . . . N14 N 0.2716(2) 0.0009(9) 0.8624(4) 0.0530(15) Uani 1 d . . . H14 H 0.2553 -0.1085 0.8557 0.064 Uiso 1 calc R . . C15 C 0.3296(3) 0.0171(11) 0.8696(5) 0.0514(18) Uani 1 d . . . O16 O 0.3558(2) 0.1670(9) 0.8792(5) 0.0849(18) Uani 1 d . . . C17 C 0.3608(3) -0.1648(11) 0.8616(5) 0.0506(17) Uani 1 d . . . H17 H 0.3511 -0.2566 0.9036 0.061 Uiso 1 calc R . . N18 N 0.4263(2) -0.1281(10) 0.8978(4) 0.0600(16) Uani 1 d . . . H18A H 0.4459 -0.2198 0.8793 0.090 Uiso 1 calc R . . H18B H 0.4381 -0.1235 0.9605 0.090 Uiso 1 calc R . . H18C H 0.4343 -0.0189 0.8752 0.090 Uiso 1 calc R . . C19 C 0.3427(3) -0.2471(11) 0.7645(5) 0.0489(17) Uani 1 d . . . C20 C 0.3419(4) -0.1259(13) 0.6850(5) 0.071(2) Uani 1 d . . . H20A H 0.3815 -0.0720 0.6964 0.085 Uiso 1 calc R . . H20B H 0.3140 -0.0235 0.6816 0.085 Uiso 1 calc R . . C21 C 0.3237(4) -0.2290(18) 0.5897(6) 0.087(3) Uani 1 d . . . H21 H 0.3234 -0.1627 0.5359 0.105 Uiso 1 calc R . . C22 C 0.3090(4) -0.404(2) 0.5817(6) 0.096(4) Uani 1 d . . . H22 H 0.2984 -0.4564 0.5217 0.115 Uiso 1 calc R . . C23 C 0.3075(6) -0.5257(16) 0.6587(8) 0.110(4) Uani 1 d . . . H23A H 0.3336 -0.6325 0.6614 0.131 Uiso 1 calc R . . H23B H 0.2670 -0.5727 0.6471 0.131 Uiso 1 calc R . . C24 C 0.3272(4) -0.4241(15) 0.7523(6) 0.076(2) Uani 1 d . . . H24 H 0.3285 -0.4933 0.8057 0.091 Uiso 1 calc R . . O30 O 0.4833(10) 0.153(3) 0.2960(13) 0.165(8) Uani 0.50 d P A 1 H30 H 0.4548 0.1576 0.2473 0.247 Uiso 0.50 calc PR A 1 C31 C 0.3865(6) 0.1451(16) 0.4386(12) 0.123(4) Uani 1 d . . . H31 H 0.3459 0.1391 0.4322 0.147 Uiso 1 calc R . . C32 C 0.4039(7) 0.1472(18) 0.3619(9) 0.120(4) Uani 1 d . . . H32 H 0.3754 0.1498 0.3024 0.144 Uiso 1 calc R . . C33 C 0.4632(7) 0.1456(16) 0.3700(8) 0.101(3) Uani 1 d . . . H33 H 0.4743 0.1445 0.3155 0.121 Uiso 0.50 calc PR B 2 C34 C 0.5093(5) 0.1456(14) 0.4603(7) 0.092(3) Uani 1 d . . . C35 C 0.5711(7) 0.1518(16) 0.4704(10) 0.126(4) Uani 1 d . . . H35 H 0.5838 0.1602 0.4175 0.151 Uiso 1 calc R . . O40 O 0.7190(2) 0.1475(8) 0.8660(4) 0.0735(15) Uani 1 d . . . O50 O 0.6085(3) 0.1763(12) 0.8901(5) 0.112(2) Uani 1 d . . . O60 O 0.4691(6) 0.2181(19) 0.8254(13) 0.267(8) Uani 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 0.0586(10) 0.0829(14) 0.0567(10) -0.0080(11) 0.0261(8) 0.0108(10) C2 0.063(4) 0.061(5) 0.046(4) -0.011(4) 0.008(3) 0.005(4) C3 0.047(3) 0.055(4) 0.050(4) -0.001(4) 0.010(3) 0.012(3) C4 0.034(3) 0.056(5) 0.055(4) -0.008(3) 0.012(3) 0.002(3) N5 0.037(2) 0.063(4) 0.047(3) -0.007(3) 0.018(2) 0.005(3) C6 0.043(3) 0.056(5) 0.058(4) -0.002(3) 0.021(3) 0.001(3) C7 0.033(3) 0.068(5) 0.063(4) -0.003(4) 0.018(3) 0.010(3) C8 0.027(3) 0.074(6) 0.050(4) -0.004(4) 0.013(3) 0.007(3) C9 0.040(3) 0.077(6) 0.050(4) -0.006(4) 0.015(3) 0.008(4) C10 0.059(4) 0.079(6) 0.079(5) 0.003(5) 0.008(4) 0.021(4) O11 0.047(2) 0.098(5) 0.106(4) -0.019(4) 0.041(3) -0.013(3) O12 0.054(3) 0.094(4) 0.059(3) -0.010(3) 0.025(2) 0.003(3) O13 0.046(2) 0.079(4) 0.056(3) 0.010(3) 0.018(2) 0.008(3) N14 0.033(2) 0.061(4) 0.069(4) -0.012(3) 0.023(3) 0.002(3) C15 0.037(3) 0.066(6) 0.053(4) -0.003(3) 0.018(3) -0.007(3) O16 0.050(3) 0.060(4) 0.153(5) 0.005(4) 0.044(3) 0.004(3) C17 0.035(3) 0.066(5) 0.056(4) 0.008(4) 0.022(3) 0.004(3) N18 0.040(3) 0.090(5) 0.055(3) 0.002(3) 0.021(2) 0.016(3) C19 0.038(3) 0.059(5) 0.055(4) 0.001(3) 0.020(3) 0.004(3) C20 0.071(5) 0.080(6) 0.059(5) 0.013(5) 0.017(4) 0.014(5) C21 0.100(7) 0.110(9) 0.059(5) 0.010(5) 0.036(5) -0.002(6) C22 0.086(6) 0.136(11) 0.067(5) -0.027(7) 0.024(4) -0.037(7) C23 0.146(10) 0.082(8) 0.109(8) -0.019(7) 0.051(8) -0.021(7) C24 0.083(5) 0.078(6) 0.074(5) 0.006(5) 0.035(4) 0.000(5) O30 0.23(2) 0.121(15) 0.121(14) 0.006(12) 0.030(13) 0.028(16) C31 0.106(8) 0.068(7) 0.165(12) 0.038(9) 0.001(9) 0.002(7) C32 0.146(12) 0.084(8) 0.103(9) 0.008(7) 0.001(8) -0.011(9) C33 0.142(10) 0.069(7) 0.083(7) -0.007(6) 0.024(7) 0.012(7) C34 0.123(8) 0.057(6) 0.091(7) -0.007(5) 0.028(6) -0.001(6) C35 0.168(13) 0.071(7) 0.160(12) -0.015(8) 0.081(11) -0.001(9) O40 0.067(3) 0.074(4) 0.074(3) -0.002(3) 0.014(2) -0.011(3) O50 0.095(4) 0.136(6) 0.116(5) 0.010(5) 0.048(4) 0.000(5) O60 0.235(13) 0.150(11) 0.48(2) 0.109(14) 0.204(15) 0.024(10) _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 C6 1.775(7) . Y S1 C2 1.797(7) . Y C2 C3 1.494(9) . Y C3 C4 1.329(8) . Y C3 C10 1.500(9) . Y C4 N5 1.417(7) . Y C4 C9 1.515(8) . Y N5 C8 1.343(8) . Y N5 C6 1.471(7) . Y C6 C7 1.570(9) . Y C7 N14 1.421(9) . Y C7 C8 1.542(8) . Y C8 O13 1.225(7) . Y C9 O11 1.235(8) . Y C9 O12 1.259(9) . Y N14 C15 1.336(7) . Y C15 O16 1.218(9) . Y C15 C17 1.511(10) . Y C17 N18 1.486(8) . Y C17 C19 1.498(9) . Y C19 C24 1.309(11) . Y C19 C20 1.462(10) . Y C20 C21 1.538(13) . Y C21 C22 1.289(15) . Y C22 C23 1.449(15) . Y C23 C24 1.511(13) . Y O30 C33 1.33(2) . Y C31 C32 1.332(17) . Y C31 C35 1.410(17) 2_656 Y C32 C33 1.357(17) . Y C33 C34 1.440(15) . Y C34 C34 1.387(19) 2_656 Y C34 C35 1.410(15) . Y C35 C31 1.410(17) 2_656 Y 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 C6 S1 C2 94.4(3) . . Y C3 C2 S1 119.2(5) . . Y C4 C3 C2 123.5(6) . . Y C4 C3 C10 123.0(6) . . Y C2 C3 C10 113.4(6) . . Y C3 C4 N5 119.5(5) . . Y C3 C4 C9 126.1(5) . . Y N5 C4 C9 114.4(5) . . Y C8 N5 C4 135.2(6) . . Y C8 N5 C6 95.8(4) . . Y C4 N5 C6 125.0(5) . . Y N5 C6 C7 86.9(5) . . Y N5 C6 S1 111.0(5) . . Y C7 C6 S1 115.8(5) . . Y N14 C7 C8 114.9(6) . . Y N14 C7 C6 119.2(6) . . Y C8 C7 C6 84.3(4) . . Y O13 C8 N5 133.0(5) . . Y O13 C8 C7 134.3(5) . . Y N5 C8 C7 92.7(5) . . Y O11 C9 O12 124.3(6) . . Y O11 C9 C4 120.1(7) . . Y O12 C9 C4 115.5(6) . . Y C15 N14 C7 121.0(6) . . Y O16 C15 N14 123.4(7) . . Y O16 C15 C17 121.4(5) . . Y N14 C15 C17 115.2(6) . . Y N18 C17 C19 111.6(5) . . Y N18 C17 C15 107.0(6) . . Y C19 C17 C15 114.5(6) . . Y C24 C19 C20 121.6(7) . . Y C24 C19 C17 119.5(7) . . Y C20 C19 C17 118.9(7) . . Y C19 C20 C21 113.5(8) . . Y C22 C21 C20 122.4(9) . . Y C21 C22 C23 125.3(10) . . Y C22 C23 C24 111.8(9) . . Y C19 C24 C23 125.5(8) . . Y C32 C31 C35 120.9(13) . 2_656 Y C31 C32 C33 120.3(12) . . Y O30 C33 C32 123.0(15) . . Y O30 C33 C34 114.7(15) . . Y C32 C33 C34 122.2(11) . . Y C34 C34 C35 119.8(13) 2_656 . Y C34 C34 C33 117.0(14) 2_656 . Y C35 C34 C33 123.1(11) . . Y C34 C35 C31 119.6(12) . 2_656 Y _diffrn_reflns_theta_full 69.90 _refine_diff_density_max 0.353 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.063 _publ_section_experimental ; Crystal colour: transparent light yellow-brown, crystal shape: regular platelet. Profile analysis combining the methods of Lehman & Larsen (1974) and Grant & Gabe (1978). Empirical absorption correction using EMPABS (North, Phillips & Mathews, 1968). Data collection parameters: \w-scan with fixed scan width and variable scan speed. Scan width 1.80%, aperture 4.00mm. Maximum scan time: 30 sec/reflection. Least-squares refinement using calculated weights: w=1/[\s^2^(Fo^2^)+(0.0947P)^2^+2.0329P] where P=(Fo^2^+2Fc^2^)/3 ; #===END data_CFBIPI # 1. SUBMISSION DETAILS _publ_contact_autor ; Dr. R. de Gelder Crystallography Department University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; _publ_contact_author_phone '031 024 3652842' _publ_contact_author_fax '031 024 3553450' _publ_contact_author_email rdg@sci.kun.nl _publ_requested_journal 'Perkin Transactions 2' _publ_requested_coeditor_name ? _publ_contact_letter ; ; #============================================================================== # 3. AUTHOR LIST loop_ _publ_author_name _publ_author_address 'G.J. Kemperman' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'R. de Gelder' ; Department of Inorganic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'F.J. Dommerholt' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'P.C. Raemakers-Franken' ; DSM Research Department of Organic Chemistry and Biotechnology P.O. Box 18 6160 MD Geleen The Netherlands ; 'A.J.H. Klunder' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'B. Zwanenburg' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; #============================================================================== # 4. TEXT _publ_section_title ; Induced Fit Phenomena in Clathrate Structures of Cephalosporins ; _publ_section_abstract ; ; _publ_section_references ; Beurskens, P. T., Beurskens, G., Bosman, W. P., Gelder, R. de, Garc\'ia-Granda, S., Gould, R. O., Isra\"el, R. & Smits, J. M. M. (1996). DIRDIF-96, A computer program system for crystal structure determination by Patterson methods and direct methods applied to difference structure factors. Crystallography Laboratory, University of Nijmegen, The Netherlands. Beurskens, P. T., Beurskens, G., Strumpel, M. & Nordman, C. E. (1987). In Patterson and Pattersons, pp. 356--367. Glusker, J. P., Patterson, B. K. & Rossi, M., Eds. Oxford, England: Clarendon Press. CAD4 EXPRESS Enraf-Nonius diffractometer control software (1994). Release 5.1, Enraf-Nonius Delft, The Netherlands. Grant, D. F. & Gabe, E. J. (1978). J. Appl. Cryst. 11, 114--120. International Tables for X-ray Crystallography (1974). Vol. IV, Birmingham, England: Kynoch Press. Lehman, M. S. & Larsen, F. K. (1974). Acta Cryst. A30, 580--584. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351--359. Sheldrick, G. M. (1997). SHELXL-97, Program for the refinement of crystal structures. University of G\"ottingen, Germany. Smits, J. M. M., Behm, H., Bosman, W. P. & Beurskens, P. T. (1988). J. Crystallogr. Spectrosc. Res. 18, 447--450. Spek, A. L. (1990). Acta Cryst. A46, C-34. Spek, A. L. (1993). PLUTON, A program for plotting molecular and crystal structures. University of Utrecht, The Netherlands. Spek, A. L. (1995). PLATON-93, Program for display and analysis of crystal and molecular structures. University of Utrecht, The Netherlands. ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #============================================================================== _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 1999-05-04 _chemical_name_systematic ; Cephradine/2,2'-bipyridyl complex ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H60 N8 O15 S2' _chemical_formula_weight 981.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 23.0227(8) _cell_length_b 7.1467(4) _cell_length_c 14.5544(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.644(3) _cell_angle_gamma 90.00 _cell_volume 2316.94(16) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 40.106 _cell_measurement_theta_max 45.680 _exptl_crystal_description 'regular platelet' _exptl_crystal_colour 'transparent colourless' _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.09 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 1.700 _exptl_absorpt_correction_type experimental #_exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.950 _exptl_absorpt_correction_T_max 1.115 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius CAD4' _diffrn_measurement_method \w/2\q-scan _diffrn_special_details ; \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.77 + 0.23tan\q)\%, range: 1.17\%-2.09\%, aperture (2.30 + 0.26tan\q)mm., range: 2.31-3.02mm. Maximum scan time: 30 sec/reflection. ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_time 7200 _diffrn_standards_decay_% 1.337 _diffrn_reflns_number 2453 _diffrn_reflns_av_R_equivalents 0.0102 _diffrn_reflns_av_sigmaI/netI 0.0176 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 69.95 _reflns_number_total 2387 _reflns_number_gt 2263 _reflns_number_observed 2263 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; CAD4 EXPRESS (Enraf-Nonius, 1994) ; #_computing_cell_refinement #; #CAD4 EXPRESS (Enraf-Nonius, 1994) #; _computing_data_reduction ; local programs (Smits et al., 1988), profile analysis (Lehman & Larsen, 1974, Grant & Gabe, 1978), EMPABS (North et al., 1968) ; _computing_structure_solution ; DIRDIF (Beurskens et al., 1996), PATTY (Beurskens et al., 1987) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLUTON (Spek, 1993), PLATON (Spek, 1990, 1995) ; _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 ; w=1/[\s^2^(Fo^2^)+(0.0694P)^2^+1.4272P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack -0.01(2) _refine_ls_number_reflns 2387 _refine_ls_number_parameters 384 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0370 _refine_ls_R_factor_obs 0.0370 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_all 0.1036 _refine_ls_wR_factor_gt 0.1005 _refine_ls_wR_factor_obs 0.1005 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_goodness_of_fit_all 1.095 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.001 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_shift/esd_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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.18312(3) 0.01254(12) 0.67631(5) 0.02620(19) Uani 1 d . . . C2 C 0.10433(14) 0.0653(5) 0.6267(2) 0.0264(6) Uani 1 d . . . H2A H 0.0980(19) 0.186(7) 0.598(3) 0.040(12) Uiso 1 d . . . H2B H 0.0915(18) -0.036(7) 0.580(3) 0.042(12) Uiso 1 d . . . C3 C 0.06315(13) 0.0653(5) 0.6934(2) 0.0283(7) Uani 1 d . . . C4 C 0.08281(12) 0.0779(6) 0.7880(2) 0.0283(7) Uani 1 d . . . N5 N 0.14473(10) 0.1019(4) 0.82984(16) 0.0259(6) Uani 1 d . . . C6 C 0.19082(13) 0.1520(5) 0.7810(2) 0.0220(6) Uani 1 d . . . H6 H 0.1911(15) 0.274(6) 0.766(2) 0.018(8) Uiso 1 d . . . C7 C 0.23838(12) 0.0857(5) 0.8720(2) 0.0219(6) Uani 1 d . . . H7 H 0.2624(15) 0.184(5) 0.906(2) 0.017(8) Uiso 1 d . . . C8 C 0.18367(12) 0.0351(5) 0.90954(18) 0.0228(7) Uani 1 d . . . C9 C 0.04392(14) 0.0893(8) 0.8579(2) 0.0428(10) Uani 1 d . . . C10 C -0.00228(14) 0.0611(7) 0.6420(3) 0.0365(8) Uani 1 d . . . H10A H -0.013(2) -0.083(8) 0.610(4) 0.058(15) Uiso 1 d . . . H10B H -0.006(2) 0.166(9) 0.602(4) 0.057(14) Uiso 1 d . . . H10C H -0.027(2) 0.054(8) 0.688(3) 0.053(13) Uiso 1 d . . . O11 O 0.00056(11) -0.0200(8) 0.8474(2) 0.0705(13) Uani 1 d . . . O12 O 0.05640(12) 0.2161(5) 0.91853(17) 0.0497(8) Uani 1 d . . . O13 O 0.17644(9) -0.0390(4) 0.98057(14) 0.0314(6) Uani 1 d . . . N14 N 0.27547(11) -0.0710(4) 0.86477(18) 0.0245(5) Uani 1 d . . . H14 H 0.260(2) -0.201(8) 0.861(3) 0.059(15) Uiso 1 d . . . C15 C 0.33394(14) -0.0445(5) 0.8657(2) 0.0292(8) Uani 1 d . . . O16 O 0.35752(11) 0.1092(5) 0.8697(2) 0.0478(7) Uani 1 d . . . C17 C 0.36855(17) -0.2240(7) 0.8610(2) 0.0430(11) Uani 1 d . . . H17 H 0.366(2) -0.300(8) 0.914(4) 0.055(13) Uiso 1 d . . . N18 N 0.43343(14) -0.1671(9) 0.8830(2) 0.0732(18) Uani 1 d . . . H18A H 0.4568 -0.2707 0.8860 0.110 Uiso 1 calc R . . H18B H 0.4435 -0.1065 0.9398 0.110 Uiso 1 calc R . . H18C H 0.4393 -0.0895 0.8366 0.110 Uiso 1 calc R . . C19 C 0.34954(17) -0.3237(6) 0.7663(2) 0.0374(9) Uani 1 d . . . C20 C 0.34218(18) -0.2109(6) 0.6774(3) 0.0349(8) Uani 1 d . . . H20A H 0.319(2) -0.107(8) 0.677(3) 0.046(13) Uiso 1 d . . . H20B H 0.384(2) -0.151(7) 0.677(3) 0.043(12) Uiso 1 d . . . C21 C 0.32218(17) -0.3246(6) 0.5891(3) 0.0371(8) Uani 1 d . . . H21 H 0.319(2) -0.261(8) 0.525(3) 0.048(13) Uiso 1 d . . . C22 C 0.31346(18) -0.5075(7) 0.5889(3) 0.0455(9) Uani 1 d . . . H22 H 0.300(2) -0.570(8) 0.526(4) 0.056(14) Uiso 1 d . . . C23 C 0.3236(3) -0.6199(7) 0.6772(4) 0.0630(15) Uani 1 d . . . H23A H 0.353(2) -0.714(10) 0.678(4) 0.064(16) Uiso 1 d . . . H23B H 0.286(3) -0.687(10) 0.675(4) 0.075(18) Uiso 1 d . . . C24 C 0.3404(2) -0.5073(7) 0.7647(3) 0.0580(13) Uani 1 d . . . H24 H 0.348(2) -0.586(8) 0.818(4) 0.062(15) Uiso 1 d . . . N30 N 0.54333(12) 0.0649(5) 0.62253(18) 0.0294(6) Uani 1 d . . . C31 C 0.53224(12) 0.0672(5) 0.5270(2) 0.0246(6) Uani 1 d . . . C32 C 0.57823(14) 0.0734(5) 0.4810(2) 0.0293(6) Uani 1 d . . . H32 H 0.5675(18) 0.084(8) 0.411(3) 0.049(12) Uiso 1 d . . . C33 C 0.63715(15) 0.0735(6) 0.5347(2) 0.0328(7) Uani 1 d . . . H33 H 0.6673(18) 0.072(7) 0.505(3) 0.037(10) Uiso 1 d . . . C34 C 0.64909(15) 0.0700(5) 0.6324(2) 0.0327(7) Uani 1 d . . . H34 H 0.687(2) 0.057(8) 0.671(3) 0.056(14) Uiso 1 d . . . C35 C 0.60093(15) 0.0658(6) 0.6726(2) 0.0332(7) Uani 1 d . . . H35 H 0.603(2) 0.061(9) 0.751(3) 0.066(15) Uiso 1 d . . . O40 O 0.72391(11) 0.0712(4) 0.86974(17) 0.0377(6) Uani 1 d . . . O50 O 0.61591(13) 0.0469(7) 0.9128(2) 0.0696(12) Uani 1 d . . . O60 O 0.47138(12) 0.1106(7) 0.76260(19) 0.0644(10) Uani 1 d . . . O70 O 0.5000 0.1945(10) 1.0000 0.098(2) Uani 1 d S . . 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 0.0248(3) 0.0329(4) 0.0219(3) -0.0057(3) 0.0078(2) 0.0027(3) C2 0.0292(14) 0.0284(17) 0.0205(13) -0.0018(12) 0.0040(11) 0.0018(13) C3 0.0238(14) 0.0339(17) 0.0247(14) -0.0024(13) 0.0019(11) 0.0060(13) C4 0.0167(12) 0.0418(18) 0.0254(14) -0.0024(14) 0.0037(11) 0.0081(14) N5 0.0187(11) 0.0392(16) 0.0191(11) -0.0026(11) 0.0033(9) 0.0093(11) C6 0.0224(13) 0.0221(15) 0.0207(13) -0.0026(12) 0.0038(11) 0.0038(12) C7 0.0183(13) 0.0244(14) 0.0228(13) -0.0029(12) 0.0046(10) 0.0023(13) C8 0.0182(12) 0.0293(19) 0.0205(13) -0.0047(13) 0.0040(10) 0.0064(12) C9 0.0242(16) 0.080(3) 0.0231(15) -0.0003(18) 0.0035(12) 0.020(2) C10 0.0252(15) 0.048(2) 0.0311(16) -0.0017(16) -0.0019(13) 0.0054(16) O11 0.0259(12) 0.140(4) 0.0513(15) -0.025(2) 0.0196(11) -0.0211(19) O12 0.0437(14) 0.079(2) 0.0272(12) -0.0064(14) 0.0111(10) 0.0255(15) O13 0.0258(10) 0.0455(16) 0.0238(10) 0.0047(10) 0.0078(8) 0.0040(10) N14 0.0198(12) 0.0258(13) 0.0278(12) -0.0020(11) 0.0058(9) 0.0051(11) C15 0.0213(14) 0.046(2) 0.0213(13) 0.0094(14) 0.0080(11) 0.0103(14) O16 0.0258(12) 0.058(2) 0.0622(17) 0.0115(15) 0.0162(12) -0.0046(13) C17 0.0397(19) 0.068(3) 0.0262(16) 0.0166(18) 0.0173(14) 0.037(2) N18 0.0272(15) 0.168(5) 0.0234(13) 0.003(2) 0.0042(12) 0.044(3) C19 0.0428(18) 0.045(2) 0.0330(17) 0.0169(16) 0.0255(15) 0.0268(17) C20 0.043(2) 0.037(2) 0.0273(16) 0.0087(15) 0.0137(14) 0.0078(17) C21 0.0419(19) 0.039(2) 0.0329(18) 0.0049(16) 0.0145(15) 0.0018(17) C22 0.048(2) 0.039(2) 0.057(2) -0.002(2) 0.0259(18) -0.001(2) C23 0.084(4) 0.036(2) 0.089(4) 0.013(2) 0.059(3) 0.011(2) C24 0.087(3) 0.046(3) 0.059(2) 0.029(2) 0.052(2) 0.034(3) N30 0.0315(13) 0.0335(15) 0.0218(11) 0.0015(11) 0.0039(9) 0.0016(12) C31 0.0267(15) 0.0224(14) 0.0239(13) 0.0007(12) 0.0051(11) 0.0017(13) C32 0.0323(15) 0.0301(15) 0.0270(14) 0.0004(13) 0.0105(12) 0.0002(14) C33 0.0309(15) 0.0290(16) 0.0395(17) 0.0000(15) 0.0111(13) 0.0020(15) C34 0.0292(15) 0.0251(15) 0.0383(17) 0.0027(15) -0.0014(13) 0.0005(14) C35 0.0363(16) 0.0326(18) 0.0268(15) 0.0014(13) 0.0008(12) 0.0014(15) O40 0.0424(13) 0.0305(12) 0.0340(12) -0.0036(10) -0.0020(10) 0.0003(11) O50 0.0512(16) 0.111(4) 0.0457(15) -0.023(2) 0.0101(12) -0.002(2) O60 0.0417(14) 0.112(3) 0.0422(14) -0.0005(19) 0.0159(11) -0.0043(19) O70 0.145(6) 0.080(4) 0.049(3) 0.000 -0.013(3) 0.000 _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 C6 1.792(3) . Y S1 C2 1.814(3) . Y C2 C3 1.519(4) . Y C3 C4 1.339(4) . Y C3 C10 1.503(4) . Y C4 N5 1.412(4) . Y C4 C9 1.518(4) . Y N5 C8 1.361(4) . Y N5 C6 1.463(4) . Y C6 C7 1.563(4) . Y C7 N14 1.428(4) . Y C7 C8 1.538(4) . Y C8 O13 1.210(4) . Y C9 O11 1.246(6) . Y C9 O12 1.247(6) . Y N14 C15 1.356(4) . Y C15 O16 1.221(5) . Y C15 C17 1.521(5) . Y C17 N18 1.502(6) . Y C17 C19 1.515(6) . Y C19 C24 1.329(7) . Y C19 C20 1.497(5) . Y C20 C21 1.492(6) . Y C21 C22 1.323(6) . Y C22 C23 1.483(7) . Y C23 C24 1.473(8) . Y N30 C35 1.342(4) . Y N30 C31 1.348(4) . Y C31 C32 1.389(4) . Y C31 C31 1.494(5) 2_656 Y C32 C33 1.384(4) . Y C33 C34 1.379(5) . Y C34 C35 1.379(5) . Y 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 C6 S1 C2 95.56(14) . . Y C3 C2 S1 117.9(2) . . Y C4 C3 C10 123.3(3) . . Y C4 C3 C2 123.6(3) . . Y C10 C3 C2 113.0(3) . . Y C3 C4 N5 119.6(3) . . Y C3 C4 C9 126.1(3) . . Y N5 C4 C9 114.0(3) . . Y C8 N5 C4 134.5(3) . . Y C8 N5 C6 95.6(2) . . Y C4 N5 C6 126.7(2) . . Y N5 C6 C7 87.3(2) . . Y N5 C6 S1 110.4(2) . . Y C7 C6 S1 116.7(2) . . Y N14 C7 C8 113.6(3) . . Y N14 C7 C6 118.6(2) . . Y C8 C7 C6 84.9(2) . . Y O13 C8 N5 132.7(3) . . Y O13 C8 C7 135.1(2) . . Y N5 C8 C7 92.1(2) . . Y O11 C9 O12 125.2(3) . . Y O11 C9 C4 118.3(4) . . Y O12 C9 C4 116.3(4) . . Y C15 N14 C7 120.0(3) . . Y O16 C15 N14 123.7(3) . . Y O16 C15 C17 122.0(3) . . Y N14 C15 C17 114.3(3) . . Y N18 C17 C19 111.4(3) . . Y N18 C17 C15 105.4(4) . . Y C19 C17 C15 113.8(3) . . Y C24 C19 C20 122.3(4) . . Y C24 C19 C17 119.2(4) . . Y C20 C19 C17 118.5(4) . . Y C21 C20 C19 113.2(4) . . Y C22 C21 C20 123.6(4) . . Y C21 C22 C23 122.9(5) . . Y C24 C23 C22 113.7(4) . . Y C19 C24 C23 124.1(4) . . Y C35 N30 C31 117.6(3) . . Y N30 C31 C32 121.9(3) . . Y N30 C31 C31 116.5(3) . 2_656 Y C32 C31 C31 121.5(3) . 2_656 Y C33 C32 C31 119.1(3) . . Y C34 C33 C32 119.6(3) . . Y C33 C34 C35 117.8(3) . . Y N30 C35 C34 124.1(3) . . Y _diffrn_reflns_theta_full 69.95 _refine_diff_density_max 0.322 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.058 _publ_section_experimental ; Crystal colour: transparent colourless, crystal shape: regular platelet. Special experimental condition: measurements were performed at -100 degrees C. Profile analysis combining the methods of Lehman & Larsen (1974) and Grant & Gabe (1978). Empirical absorption correction using EMPABS (North, Phillips & Mathews, 1968). Data collection parameters: \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.77 + 0.23tan\q)\%, range: 1.17\%-2.09\%, aperture (2.30 + 0.26tan\q)mm., range: 2.31-3.02mm. Maximum scan time: 30 sec/reflection. Least-squares refinement using calculated weights: w=1/[\s^2^(Fo^2^)+(0.0694P)^2^+1.4272P] where P=(Fo^2^+2Fc^2^)/3 ; #===END data_CEFRNA # 1. SUBMISSION DETAILS _publ_contact_autor ; Dr. R. de Gelder Crystallography Department University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; _publ_contact_author_phone '031 024 3652842' _publ_contact_author_fax '031 024 3553450' _publ_contact_author_email rdg@sci.kun.nl _publ_requested_journal 'Perkin Transactions 2' _publ_requested_coeditor_name ? _publ_contact_letter ; ; #============================================================================== # 3. AUTHOR LIST loop_ _publ_author_name _publ_author_address 'G.J. Kemperman' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'R. de Gelder' ; Department of Inorganic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'F.J. Dommerholt' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'P.C. Raemakers-Franken' ; DSM Research Department of Organic Chemistry and Biotechnology P.O. Box 18 6160 MD Geleen The Netherlands ; 'A.J.H. Klunder' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'B. Zwanenburg' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; #============================================================================== # 4. TEXT _publ_section_title ; Induced Fit Phenomena in Clathrate Structures of Cephalosporins ; _publ_section_abstract ; ; _publ_section_references ; Beurskens, P. T., Beurskens, G., Bosman, W. P., Gelder, R. de, Garc\'ia-Granda, S., Gould, R. O., Isra\"el, R. & Smits, J. M. M. (1996). DIRDIF-96, A computer program system for crystal structure determination by Patterson methods and direct methods applied to difference structure factors. Crystallography Laboratory, University of Nijmegen, The Netherlands. CAD4 EXPRESS Enraf-Nonius diffractometer control software (1994). Release 5.1, Enraf-Nonius Delft, The Netherlands. Grant, D. F. & Gabe, E. J. (1978). J. Appl. Cryst. 11, 114--120. International Tables for X-ray Crystallography (1974). Vol. IV, Birmingham, England: Kynoch Press. Lehman, M. S. & Larsen, F. K. (1974). Acta Cryst. A30, 580--584. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351--359. Sheldrick, G. M. (1997). SHELXL-97, Program for the refinement of crystal structures. University of G\"ottingen, Germany. Smits, J. M. M., Behm, H., Bosman, W. P. & Beurskens, P. T. (1988). J. Crystallogr. Spectrosc. Res. 18, 447--450. Spek, A. L. (1990). Acta Cryst. A46, C-34. Spek, A. L. (1993). PLUTON, A program for plotting molecular and crystal structures. University of Utrecht, The Netherlands. Spek, A. L. (1995). PLATON-93, Program for display and analysis of crystal and molecular structures. University of Utrecht, The Netherlands. ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #============================================================================== _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 1999-05-04 _chemical_name_systematic ; Cephradine/naphthalene complex ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H58 N6 O14.50 S2' _chemical_formula_weight 943.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 23.4584(6) _cell_length_b 7.1179(2) _cell_length_c 14.8922(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.571(2) _cell_angle_gamma 90.00 _cell_volume 2357.12(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 40.492 _cell_measurement_theta_max 46.469 _exptl_crystal_description 'regular platelet' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 1.629 _exptl_absorpt_correction_type experimental #_exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.932 _exptl_absorpt_correction_T_max 1.072 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius CAD4' _diffrn_measurement_method \w/2\q-scan _diffrn_special_details ; \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.40 + 0.19tan\q)\%, range: 0.61\%-1.38\%, aperture (1.30 + 0.15tan\q)mm., range: 1.31-1.70mm. Maximum scan time: 30 sec/reflection. ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_time 7200 _diffrn_standards_decay_% 2.366 _diffrn_reflns_number 2522 _diffrn_reflns_av_R_equivalents 0.0149 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 69.91 _reflns_number_total 2425 _reflns_number_gt 2236 _reflns_number_observed 2236 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; CAD4 EXPRESS (Enraf-Nonius, 1994) ; #_computing_cell_refinement #; #CAD4 EXPRESS (Enraf-Nonius, 1994) #; _computing_data_reduction ; local programs (Smits et al., 1988), profile analysis (Lehman & Larsen, 1974, Grant & Gabe, 1978), EMPABS (North et al., 1968) ; _computing_structure_solution ; DIRDIF (Beurskens et al., 1996), ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLUTON (Spek, 1993), PLATON (Spek, 1990, 1995) ; _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 ; w=1/[\s^2^(Fo^2^)+(0.0814P)^2^+1.5154P] 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 0.0015(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 2425 _refine_ls_number_parameters 297 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0435 _refine_ls_R_factor_obs 0.0435 _refine_ls_wR_factor_ref 0.1389 _refine_ls_wR_factor_all 0.1389 _refine_ls_wR_factor_gt 0.1229 _refine_ls_wR_factor_obs 0.1229 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_goodness_of_fit_all 1.149 _refine_ls_restrained_S_all 1.149 _refine_ls_shift/su_max 0.001 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_shift/esd_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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.17083(5) 1.06906(17) 0.67615(7) 0.0492(3) Uani 1 d . . . C2 C 0.09196(19) 1.1328(7) 0.6269(3) 0.0466(10) Uani 1 d . . . H2A H 0.0897 1.2524 0.5947 0.056 Uiso 1 calc R . . H2B H 0.0725 1.0402 0.5792 0.056 Uiso 1 calc R . . C3 C 0.05593(17) 1.1493(7) 0.6942(3) 0.0414(8) Uani 1 d . . . C4 C 0.07985(14) 1.1743(6) 0.7870(2) 0.0353(8) Uani 1 d . . . N5 N 0.14308(12) 1.1925(5) 0.8272(2) 0.0355(7) Uani 1 d . . . C6 C 0.18560(16) 1.2261(6) 0.7752(3) 0.0387(8) Uani 1 d . . . H6 H 0.1883 1.3583 0.7585 0.046 Uiso 1 calc R . . C7 C 0.23652(15) 1.1634(6) 0.8663(3) 0.0368(8) Uani 1 d . . . H7 H 0.2615 1.2693 0.8985 0.044 Uiso 1 calc R . . C8 C 0.18433(15) 1.1237(6) 0.9059(2) 0.0366(9) Uani 1 d . . . C9 C 0.04528(15) 1.2080(6) 0.8559(3) 0.0391(9) Uani 1 d . . . C10 C -0.01114(19) 1.1478(9) 0.6433(3) 0.0583(12) Uani 1 d . . . H10A H -0.0232 1.0253 0.6172 0.088 Uiso 1 calc R . . H10B H -0.0207 1.2390 0.5932 0.088 Uiso 1 calc R . . H10C H -0.0321 1.1782 0.6873 0.088 Uiso 1 calc R . . O11 O -0.00069(12) 1.1134(5) 0.8472(2) 0.0597(10) Uani 1 d . . . O12 O 0.06497(12) 1.3360(5) 0.91590(19) 0.0501(8) Uani 1 d . . . O13 O 0.18061(11) 1.0543(6) 0.97836(18) 0.0482(7) Uani 1 d . . . N14 N 0.27174(13) 1.0023(5) 0.8615(2) 0.0405(8) Uani 1 d . . . H14 H 0.2552 0.8931 0.8543 0.049 Uiso 1 calc R . . C15 C 0.32973(16) 1.0170(6) 0.8680(3) 0.0377(8) Uani 1 d . . . O16 O 0.35640(14) 1.1665(5) 0.8795(3) 0.0659(10) Uani 1 d . . . C17 C 0.36092(15) 0.8317(6) 0.8617(3) 0.0368(8) Uani 1 d . . . H17 H 0.3516 0.7414 0.9047 0.044 Uiso 1 calc R . . N18 N 0.42723(13) 0.8707(6) 0.8969(2) 0.0449(8) Uani 1 d . . . H18A H 0.4468 0.7772 0.8798 0.067 Uiso 1 calc R . . H18B H 0.4395 0.8801 0.9598 0.067 Uiso 1 calc R . . H18C H 0.4347 0.9779 0.8720 0.067 Uiso 1 calc R . . C19 C 0.34131(16) 0.7486(6) 0.7633(3) 0.0395(9) Uani 1 d . . . C20 C 0.3408(2) 0.8717(8) 0.6828(3) 0.0548(11) Uani 1 d . . . H20A H 0.3806 0.9246 0.6943 0.066 Uiso 1 calc R . . H20B H 0.3131 0.9747 0.6789 0.066 Uiso 1 calc R . . C21 C 0.3227(3) 0.7687(10) 0.5902(4) 0.0664(15) Uani 1 d . . . H21 H 0.3223 0.8356 0.5363 0.080 Uiso 1 calc R . . C22 C 0.3074(3) 0.5892(11) 0.5798(4) 0.0729(17) Uani 1 d . . . H22 H 0.2966 0.5367 0.5195 0.088 Uiso 1 calc R . . C23 C 0.3069(4) 0.4709(11) 0.6593(5) 0.0875(19) Uani 1 d . . . H23A H 0.3336 0.3652 0.6630 0.105 Uiso 1 calc R . . H23B H 0.2666 0.4215 0.6475 0.105 Uiso 1 calc R . . C24 C 0.3255(2) 0.5706(8) 0.7522(3) 0.0572(11) Uani 1 d . . . H24 H 0.3261 0.5026 0.8058 0.069 Uiso 1 calc R . . C30 C 0.4930(3) 0.1450(8) 0.5427(4) 0.0717(15) Uani 1 d . . . C31 C 0.4319(4) 0.1458(10) 0.5380(7) 0.102(3) Uani 1 d . . . H31 H 0.4220 0.1449 0.5937 0.122 Uiso 1 calc R . . C32 C 0.3872(4) 0.1478(12) 0.4529(11) 0.129(4) Uani 1 d . . . H32 H 0.3472 0.1488 0.4508 0.154 Uiso 1 calc R . . C33 C 0.4014(6) 0.1483(13) 0.3706(8) 0.131(4) Uani 1 d . . . H33 H 0.3708 0.1518 0.3127 0.158 Uiso 1 calc R . . C34 C 0.5406(5) 0.1438(11) 0.6277(5) 0.097(2) Uani 1 d . . . H34 H 0.5322 0.1399 0.6847 0.117 Uiso 1 calc R . . O40 O 0.21718(14) 0.6485(6) 0.8631(2) 0.0573(8) Uani 1 d . . . O50 O 0.10781(18) 0.6832(8) 0.8930(3) 0.0818(12) Uani 1 d . . . O60 O 0.4684(3) 0.2044(10) 0.8135(4) 0.1155(19) Uani 1 d . . . O70 O 0.0000 0.835(11) 1.0000 0.48(5) Uani 0.50 d SP . . 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 0.0504(5) 0.0615(7) 0.0412(5) -0.0080(5) 0.0223(4) 0.0087(5) C2 0.053(2) 0.052(3) 0.0324(18) -0.0025(18) 0.0106(16) 0.008(2) C3 0.0364(18) 0.043(2) 0.0393(18) -0.0034(17) 0.0037(14) 0.0061(17) C4 0.0248(15) 0.041(2) 0.0389(17) -0.0005(16) 0.0083(13) 0.0083(15) N5 0.0251(13) 0.050(2) 0.0331(14) -0.0045(14) 0.0117(11) 0.0034(13) C6 0.0355(17) 0.043(2) 0.0426(18) 0.0010(17) 0.0190(15) 0.0024(16) C7 0.0266(15) 0.040(2) 0.0446(19) -0.0058(17) 0.0129(14) 0.0024(16) C8 0.0264(15) 0.048(2) 0.0361(17) -0.0022(16) 0.0109(13) 0.0087(15) C9 0.0289(16) 0.049(2) 0.0403(18) -0.0002(18) 0.0128(14) 0.0100(16) C10 0.041(2) 0.069(3) 0.051(2) -0.005(2) -0.0051(17) 0.008(2) O11 0.0367(14) 0.069(3) 0.082(2) -0.0170(18) 0.0310(14) -0.0068(15) O12 0.0421(14) 0.071(2) 0.0414(14) -0.0132(15) 0.0192(11) 0.0006(15) O13 0.0363(13) 0.070(2) 0.0389(13) 0.0082(16) 0.0137(10) 0.0104(15) N14 0.0245(13) 0.0411(18) 0.0588(19) -0.0060(15) 0.0173(13) 0.0010(13) C15 0.0297(16) 0.042(2) 0.0462(19) 0.0032(17) 0.0191(14) 0.0013(16) O16 0.0402(15) 0.0469(19) 0.121(3) 0.005(2) 0.0403(17) 0.0014(15) C17 0.0269(16) 0.045(2) 0.0416(18) 0.0051(17) 0.0155(14) 0.0052(16) N18 0.0271(14) 0.065(2) 0.0437(16) 0.0038(17) 0.0127(12) 0.0092(15) C19 0.0303(17) 0.048(2) 0.0438(19) 0.0087(18) 0.0173(15) 0.0076(16) C20 0.062(3) 0.059(3) 0.043(2) 0.006(2) 0.0161(19) -0.001(2) C21 0.070(3) 0.086(4) 0.042(2) 0.005(3) 0.017(2) -0.004(3) C22 0.079(3) 0.094(5) 0.046(2) -0.018(3) 0.020(2) -0.021(4) C23 0.116(5) 0.069(4) 0.080(4) -0.018(3) 0.034(4) -0.017(4) C24 0.074(3) 0.049(2) 0.056(2) 0.002(2) 0.030(2) -0.004(3) C30 0.110(4) 0.040(2) 0.067(3) 0.004(3) 0.031(3) 0.001(3) C31 0.126(6) 0.053(3) 0.154(7) 0.019(5) 0.082(6) -0.002(4) C32 0.092(5) 0.055(4) 0.213(12) 0.027(7) 0.012(7) -0.008(4) C33 0.161(10) 0.057(4) 0.124(8) 0.010(5) -0.029(7) -0.018(6) C34 0.147(7) 0.056(4) 0.073(4) 0.007(3) 0.013(4) 0.003(5) O40 0.0550(17) 0.0529(18) 0.0607(18) -0.0045(16) 0.0136(14) -0.0086(16) O50 0.073(2) 0.093(3) 0.085(3) -0.002(3) 0.0327(19) -0.014(2) O60 0.119(4) 0.108(5) 0.137(4) 0.004(4) 0.066(3) -0.021(4) O70 0.82(13) 0.34(8) 0.15(3) 0.000 -0.04(5) 0.000 _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 C6 1.794(4) . Y S1 C2 1.817(4) . Y C2 C3 1.508(6) . Y C3 C4 1.328(5) . Y C3 C10 1.513(5) . Y C4 N5 1.418(4) . Y C4 C9 1.515(5) . Y N5 C8 1.352(5) . Y N5 C6 1.465(4) . Y C6 C7 1.561(5) . Y C7 N14 1.428(5) . Y C7 C8 1.545(5) . Y C8 O13 1.215(5) . Y C9 O11 1.243(5) . Y C9 O12 1.257(5) . Y N14 C15 1.337(4) . Y C15 O16 1.219(5) . Y C15 C17 1.525(6) . Y C17 N18 1.501(4) . Y C17 C19 1.511(6) . Y C19 C24 1.315(7) . Y C19 C20 1.482(6) . Y C20 C21 1.499(7) . Y C21 C22 1.323(10) . Y C22 C23 1.457(10) . Y C23 C24 1.491(8) . Y C30 C34 1.396(10) . Y C30 C30 1.410(12) 2_656 Y C30 C31 1.413(10) . Y C31 C32 1.363(14) . Y C32 C33 1.369(16) . Y C33 C34 1.352(15) 2_656 Y C34 C33 1.352(15) 2_656 Y 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 C6 S1 C2 94.67(18) . . Y C3 C2 S1 117.7(3) . . Y C4 C3 C2 124.2(3) . . Y C4 C3 C10 123.3(4) . . Y C2 C3 C10 112.3(3) . . Y C3 C4 N5 119.4(3) . . Y C3 C4 C9 125.8(3) . . Y N5 C4 C9 114.4(3) . . Y C8 N5 C4 134.2(3) . . Y C8 N5 C6 95.6(3) . . Y C4 N5 C6 126.1(3) . . Y N5 C6 C7 87.4(3) . . Y N5 C6 S1 110.3(3) . . Y C7 C6 S1 115.5(3) . . Y N14 C7 C8 114.4(3) . . Y N14 C7 C6 118.7(3) . . Y C8 C7 C6 84.5(2) . . Y O13 C8 N5 133.1(3) . . Y O13 C8 C7 134.7(3) . . Y N5 C8 C7 92.2(3) . . Y O11 C9 O12 125.2(3) . . Y O11 C9 C4 118.5(4) . . Y O12 C9 C4 116.2(3) . . Y C15 N14 C7 121.7(3) . . Y O16 C15 N14 122.9(4) . . Y O16 C15 C17 121.9(3) . . Y N14 C15 C17 115.2(3) . . Y N18 C17 C19 111.9(3) . . Y N18 C17 C15 106.4(3) . . Y C19 C17 C15 113.2(3) . . Y C24 C19 C20 122.6(4) . . Y C24 C19 C17 119.0(4) . . Y C20 C19 C17 118.4(4) . . Y C19 C20 C21 112.5(5) . . Y C22 C21 C20 124.5(5) . . Y C21 C22 C23 122.4(5) . . Y C22 C23 C24 113.8(6) . . Y C19 C24 C23 124.2(5) . . Y C34 C30 C30 118.0(9) . 2_656 Y C34 C30 C31 123.4(7) . . Y C30 C30 C31 118.6(8) 2_656 . Y C32 C31 C30 120.9(9) . . Y C31 C32 C33 119.8(10) . . Y C34 C33 C32 120.9(9) 2_656 . Y C33 C34 C30 121.7(9) 2_656 . Y _diffrn_reflns_theta_full 69.91 _refine_diff_density_max 0.355 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.058 _publ_section_experimental ; Crystal colour: colourless, crystal shape: regular platelet. Profile analysis combining the methods of Lehman & Larsen (1974) and Grant & Gabe (1978). Empirical absorption correction using EMPABS (North, Phillips & Mathews, 1968). Data collection parameters: \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.40 + 0.19tan\q)\%, range: 0.61\%-1.38\%, aperture (1.30 + 0.15tan\q)mm., range: 1.31-1.70mm. Maximum scan time: 30 sec/reflection. Least-squares refinement using calculated weights: w=1/[\s^2^(Fo^2^)+(0.0814P)^2^+1.5154P] where P=(Fo^2^+2Fc^2^)/3 ; #===END data_CF2ACN # 1. SUBMISSION DETAILS _publ_contact_autor ; Dr. R. de Gelder Crystallography Department University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; _publ_contact_author_phone '031 024 3652842' _publ_contact_author_fax '031 024 3553450' _publ_contact_author_email rdg@sci.kun.nl _publ_requested_journal 'Perkin Transactions 2' _publ_requested_coeditor_name ? _publ_contact_letter ; ; #============================================================================== # 3. AUTHOR LIST loop_ _publ_author_name _publ_author_address 'G.J. Kemperman' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'R. de Gelder' ; Department of Inorganic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'F.J. Dommerholt' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'P.C. Raemakers-Franken' ; DSM Research Department of Organic Chemistry and Biotechnology P.O. Box 18 6160 MD Geleen The Netherlands ; 'A.J.H. Klunder' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'B. Zwanenburg' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; #============================================================================== # 4. TEXT _publ_section_title ; Induced Fit Phenomena in Clathrate Structures of Cephalosporins ; _publ_section_abstract ; ; _publ_section_references ; Beurskens, P. T., Beurskens, G., Bosman, W. P., Gelder, R. de, Garc\'ia-Granda, S., Gould, R. O., Isra\"el, R. & Smits, J. M. M. (1996). DIRDIF-96, A computer program system for crystal structure determination by Patterson methods and direct methods applied to difference structure factors. Crystallography Laboratory, University of Nijmegen, The Netherlands. CAD4 EXPRESS Enraf-Nonius diffractometer control software (1994). Release 5.1, Enraf-Nonius Delft, The Netherlands. Grant, D. F. & Gabe, E. J. (1978). J. Appl. Cryst. 11, 114--120. International Tables for X-ray Crystallography (1974). Vol. IV, Birmingham, England: Kynoch Press. Lehman, M. S. & Larsen, F. K. (1974). Acta Cryst. A30, 580--584. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351--359. Sheldrick, G. M. (1997). SHELXL-97, Program for the refinement of crystal structures. University of G\"ottingen, Germany. Smits, J. M. M., Behm, H., Bosman, W. P. & Beurskens, P. T. (1988). J. Crystallogr. Spectrosc. Res. 18, 447--450. Spek, A. L. (1990). Acta Cryst. A46, C-34. Spek, A. L. (1993). PLUTON, A program for plotting molecular and crystal structures. University of Utrecht, The Netherlands. Spek, A. L. (1995). PLATON-93, Program for display and analysis of crystal and molecular structures. University of Utrecht, The Netherlands. ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #============================================================================== _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 1999-05-04 _chemical_name_systematic ; Cephradine/2-acetonaphthone complex ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H57 N6 O13.50 S2' _chemical_formula_weight 950.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 23.3855(5) _cell_length_b 7.1965(3) _cell_length_c 14.7588(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.580(3) _cell_angle_gamma 90.00 _cell_volume 2354.36(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 39.960 _cell_measurement_theta_max 46.191 _exptl_crystal_description 'regular thick needle' _exptl_crystal_colour 'transparent colourless' _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1006 _exptl_absorpt_coefficient_mu 1.620 _exptl_absorpt_correction_type experimental #_exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 1.030 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius CAD4' _diffrn_measurement_method \w/2\q-scan _diffrn_special_details ; \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.48 + 0.17tan\q)\%, range: 0.74\%-1.43\%, aperture (1.51 + 0.09tan\q)mm., range: 1.52-1.75mm. Maximum scan time: 30 sec/reflection. ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_time 900 _diffrn_standards_decay_% 2.010 _diffrn_reflns_number 2507 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0120 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 69.88 _reflns_number_total 2410 _reflns_number_gt 2329 _reflns_number_observed 2329 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; CAD4 EXPRESS (Enraf-Nonius, 1994) ; #_computing_cell_refinement #; #CAD4 EXPRESS (Enraf-Nonius, 1994) #; _computing_data_reduction ; local programs (Smits et al., 1988), profile analysis (Lehman & Larsen, 1974, Grant & Gabe, 1978), EMPABS (North et al., 1968) ; _computing_structure_solution ; DIRDIF (Beurskens et al., 1996), ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLUTON (Spek, 1993), PLATON (Spek, 1990, 1995) ; _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 ; w=1/[\s^2^(Fo^2^)+(0.0697P)^2^+0.4696P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack 0.04(2) _refine_ls_number_reflns 2410 _refine_ls_number_parameters 445 _refine_ls_number_restraints 71 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0329 _refine_ls_R_factor_obs 0.0329 _refine_ls_wR_factor_ref 0.0914 _refine_ls_wR_factor_all 0.0914 _refine_ls_wR_factor_gt 0.0899 _refine_ls_wR_factor_obs 0.0899 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_goodness_of_fit_all 1.029 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_shift/esd_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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.17453(3) 0.10077(11) 0.67852(4) 0.0591(2) Uani 1 d . . . C2 C 0.09633(14) 0.1698(5) 0.62657(18) 0.0554(6) Uani 1 d . . . H2A H 0.0940(18) 0.287(7) 0.588(3) 0.084(12) Uiso 1 d . . . H2B H 0.0799(13) 0.083(5) 0.584(2) 0.049(7) Uiso 1 d . . . C3 C 0.05883(11) 0.1837(4) 0.69290(16) 0.0474(5) Uani 1 d . . . C4 C 0.08196(9) 0.2030(4) 0.78779(15) 0.0425(5) Uani 1 d . . . N5 N 0.14502(8) 0.2187(3) 0.83029(12) 0.0426(4) Uani 1 d . . . C6 C 0.18889(11) 0.2501(4) 0.78036(18) 0.0467(5) Uani 1 d . . . H6 H 0.1899(11) 0.369(4) 0.7600(18) 0.038(6) Uiso 1 d . . . C7 C 0.23840(10) 0.1856(4) 0.87248(19) 0.0473(5) Uani 1 d . . . H7 H 0.2665(13) 0.288(5) 0.904(2) 0.055(8) Uiso 1 d . . . C8 C 0.18539(9) 0.1482(4) 0.91064(15) 0.0457(6) Uani 1 d . . . C9 C 0.04544(9) 0.2310(4) 0.85483(16) 0.0461(5) Uani 1 d . . . C10 C -0.00775(13) 0.1850(6) 0.6399(2) 0.0665(8) Uani 1 d . . . H10A H -0.0207(18) 0.068(7) 0.615(3) 0.080(12) Uiso 1 d . . . H10B H -0.0157(18) 0.274(7) 0.578(3) 0.085(12) Uiso 1 d . . . H10C H -0.0309(18) 0.224(8) 0.681(3) 0.093(13) Uiso 1 d . . . O11 O -0.00119(8) 0.1377(4) 0.84215(16) 0.0702(6) Uani 1 d . . . O12 O 0.06451(8) 0.3534(4) 0.91760(12) 0.0603(5) Uani 1 d . . . O13 O 0.18048(7) 0.0791(4) 0.98253(11) 0.0584(5) Uani 1 d . . . N14 N 0.27311(8) 0.0229(3) 0.86825(17) 0.0492(5) Uani 1 d . . . H14 H 0.2560(17) -0.083(6) 0.860(3) 0.074(11) Uiso 1 d . . . C15 C 0.33012(9) 0.0366(4) 0.86912(15) 0.0412(5) Uani 1 d . . . O16 O 0.35632(9) 0.1845(3) 0.87609(19) 0.0721(6) Uani 1 d . . . C17 C 0.36088(9) -0.1465(4) 0.86153(15) 0.0400(5) Uani 1 d . . . H17 H 0.3531(11) -0.239(4) 0.9022(19) 0.042(7) Uiso 1 d . . . N18 N 0.42723(8) -0.1111(4) 0.89655(14) 0.0496(5) Uani 1 d . . . H18A H 0.4548(18) -0.214(7) 0.880(3) 0.087(12) Uiso 1 d . . . H18B H 0.4397(12) -0.104(4) 0.964(2) 0.047(7) Uiso 1 d . . . H18C H 0.4395(15) 0.005(6) 0.875(2) 0.060(9) Uiso 1 d . . . C19 C 0.34049(9) -0.2264(3) 0.76145(15) 0.0412(5) Uani 1 d . . . C20 C 0.34217(14) -0.1036(5) 0.68151(18) 0.0580(6) Uani 1 d . . . H20A H 0.3878(18) -0.061(7) 0.697(3) 0.087(12) Uiso 1 d . . . H20B H 0.3128(19) 0.006(8) 0.683(3) 0.087(12) Uiso 1 d . . . C21 C 0.32349(15) -0.2024(7) 0.5868(2) 0.0733(9) Uani 1 d . . . H21 H 0.327(2) -0.110(9) 0.527(4) 0.121(17) Uiso 1 d . . . C22 C 0.30606(17) -0.3754(7) 0.5750(2) 0.0803(11) Uani 1 d . . . H22 H 0.2975(18) -0.413(8) 0.513(3) 0.090(12) Uiso 1 d . . . C23 C 0.3020(3) -0.4953(7) 0.6533(3) 0.0893(11) Uani 1 d . . . H23A H 0.338(2) -0.574(8) 0.660(3) 0.103(15) Uiso 1 d . . . H23B H 0.255(3) -0.555(12) 0.634(4) 0.17(3) Uiso 1 d . . . C24 C 0.32282(14) -0.4026(5) 0.7490(2) 0.0604(6) Uani 1 d . . . H24 H 0.3210(15) -0.469(6) 0.800(3) 0.072(10) Uiso 1 d . . . C30 C 0.5958(3) 0.1918(9) 0.6835(6) 0.0668(15) Uani 0.50 d PD . . C31 C 0.5339(3) 0.1902(9) 0.6606(5) 0.0593(14) Uani 0.50 d PD . . H31 H 0.5168 0.1953 0.7095 0.071 Uiso 0.50 calc PR . . C32 C 0.4954(3) 0.1811(19) 0.5643(6) 0.068(3) Uani 0.50 d PD . . C33 C 0.4325(4) 0.1841(16) 0.5430(7) 0.084(3) Uani 0.50 d PD . . H33 H 0.4153 0.1881 0.5918 0.101 Uiso 0.50 calc PR . . C34 C 0.3965(6) 0.181(3) 0.4481(8) 0.113(6) Uani 0.50 d PD . . H34 H 0.3548 0.1826 0.4335 0.136 Uiso 0.50 calc PR . . C35 C 0.4214(6) 0.1753(14) 0.3745(7) 0.116(6) Uani 0.50 d PD . . H35 H 0.3967 0.1722 0.3111 0.140 Uiso 0.50 calc PR . . C36 C 0.4836(6) 0.174(2) 0.3970(9) 0.103(5) Uani 0.50 d PD . . H36 H 0.5004 0.1723 0.3477 0.123 Uiso 0.50 calc PR . . C37 C 0.5217(5) 0.1760(12) 0.4910(6) 0.084(3) Uani 0.50 d PD . . C38 C 0.5847(5) 0.173(2) 0.5147(8) 0.100(6) Uani 0.50 d PD . . H38 H 0.6021 0.1638 0.4664 0.120 Uiso 0.50 calc PR . . C39 C 0.6213(4) 0.1839(13) 0.6092(8) 0.091(3) Uani 0.50 d PD . . H39 H 0.6630 0.1860 0.6236 0.109 Uiso 0.50 calc PR . . C40 C 0.6358(3) 0.2069(8) 0.7862(6) 0.0759(19) Uani 0.50 d P A 1 O41 O 0.6897(3) 0.2031(9) 0.8022(6) 0.107(2) Uani 0.50 d P A 1 C41 C 0.6073(11) 0.226(2) 0.8687(18) 0.079(5) Uani 0.50 d P A 1 H41A H 0.5993 0.1050 0.8888 0.118 Uiso 0.50 calc PR A 1 H41B H 0.5704 0.2952 0.8460 0.118 Uiso 0.50 calc PR A 1 H41C H 0.6350 0.2905 0.9217 0.118 Uiso 0.50 calc PR A 1 O40 O 0.7167(2) 0.1721(7) 0.8622(3) 0.0639(10) Uani 0.50 d P B 2 O50 O 0.6070(8) 0.216(2) 0.8872(14) 0.102(5) Uani 0.50 d P C 2 O60 O 0.4585(2) 0.2550(8) 0.8049(4) 0.163(2) Uani 1 d . . . O70 O 0.5000 0.264(7) 1.0000 0.330(19) Uani 0.50 d SP . . 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 0.0649(4) 0.0701(4) 0.0530(3) -0.0079(3) 0.0337(3) 0.0114(3) C2 0.0691(15) 0.0586(15) 0.0382(11) 0.0011(12) 0.0166(11) 0.0120(14) C3 0.0486(11) 0.0490(12) 0.0412(10) 0.0003(10) 0.0094(9) 0.0111(11) C4 0.0331(9) 0.0523(13) 0.0431(10) 0.0010(10) 0.0133(8) 0.0115(10) N5 0.0331(8) 0.0585(12) 0.0402(8) -0.0036(9) 0.0172(7) 0.0069(8) C6 0.0452(11) 0.0480(13) 0.0568(13) -0.0032(11) 0.0302(10) 0.0033(10) C7 0.0332(10) 0.0483(12) 0.0650(13) -0.0102(11) 0.0220(9) 0.0028(10) C8 0.0303(9) 0.0605(16) 0.0473(11) -0.0098(10) 0.0139(8) 0.0080(9) C9 0.0331(9) 0.0602(14) 0.0469(11) 0.0044(11) 0.0154(8) 0.0142(10) C10 0.0546(14) 0.0721(19) 0.0562(15) -0.0043(15) -0.0060(12) 0.0134(15) O11 0.0453(9) 0.0801(16) 0.0974(14) -0.0156(12) 0.0398(9) -0.0010(10) O12 0.0479(8) 0.0909(15) 0.0460(8) -0.0123(10) 0.0205(7) 0.0038(10) O13 0.0464(8) 0.0854(14) 0.0451(8) 0.0071(10) 0.0170(6) 0.0179(9) N14 0.0293(8) 0.0467(11) 0.0755(13) -0.0125(10) 0.0224(8) 0.0004(8) C15 0.0305(9) 0.0512(12) 0.0450(10) 0.0022(9) 0.0164(8) 0.0035(9) O16 0.0477(9) 0.0575(11) 0.1243(19) 0.0032(13) 0.0460(11) -0.0026(9) C17 0.0308(9) 0.0523(13) 0.0400(10) 0.0062(10) 0.0155(8) 0.0078(9) N18 0.0296(8) 0.0779(16) 0.0422(10) 0.0010(10) 0.0126(7) 0.0111(10) C19 0.0330(9) 0.0537(13) 0.0399(10) 0.0039(9) 0.0160(8) 0.0081(9) C20 0.0659(16) 0.0659(17) 0.0441(12) 0.0068(12) 0.0202(11) 0.0002(14) C21 0.0733(18) 0.105(3) 0.0417(13) 0.0054(16) 0.0183(12) -0.0079(19) C22 0.085(2) 0.105(3) 0.0516(15) -0.0212(19) 0.0219(14) -0.019(2) C23 0.110(3) 0.081(3) 0.077(2) -0.019(2) 0.030(2) -0.018(3) C24 0.0713(16) 0.0580(15) 0.0563(14) 0.0009(14) 0.0264(12) -0.0046(15) C30 0.073(4) 0.036(3) 0.097(5) -0.003(3) 0.034(4) -0.005(3) C31 0.062(3) 0.043(3) 0.074(4) 0.002(3) 0.024(3) -0.004(3) C32 0.086(5) 0.043(4) 0.071(8) -0.007(8) 0.019(6) -0.010(5) C33 0.084(4) 0.060(4) 0.095(6) 0.011(6) 0.009(5) -0.015(4) C34 0.140(10) 0.059(6) 0.102(10) 0.019(8) -0.015(8) -0.018(6) C35 0.199(16) 0.053(4) 0.066(6) -0.005(4) -0.001(9) -0.011(8) C36 0.182(17) 0.053(4) 0.069(9) 0.002(8) 0.035(9) 0.000(11) C37 0.143(11) 0.036(3) 0.089(5) -0.006(5) 0.057(7) -0.006(4) C38 0.163(16) 0.052(5) 0.119(13) -0.014(11) 0.094(14) -0.004(11) C39 0.108(7) 0.047(3) 0.148(10) -0.013(6) 0.084(7) -0.009(5) C40 0.057(3) 0.038(3) 0.124(6) 0.007(3) 0.017(3) -0.003(2) O41 0.062(3) 0.068(3) 0.174(7) 0.008(4) 0.015(4) 0.002(3) C41 0.084(10) 0.050(5) 0.083(7) -0.001(4) 0.001(6) -0.007(5) O40 0.058(2) 0.056(2) 0.074(2) -0.007(2) 0.0163(19) -0.009(2) O50 0.074(7) 0.121(9) 0.116(10) -0.009(6) 0.036(6) -0.016(6) O60 0.187(4) 0.155(4) 0.171(4) -0.028(3) 0.091(3) -0.086(4) O70 0.183(17) 0.37(5) 0.40(4) 0.000 0.04(2) 0.000 _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 C6 1.790(3) . Y S1 C2 1.813(3) . Y C2 C3 1.511(4) . Y C3 C4 1.338(3) . Y C3 C10 1.503(3) . Y C4 N5 1.411(3) . Y C4 C9 1.512(3) . Y N5 C8 1.357(3) . Y N5 C6 1.459(3) . Y C6 C7 1.550(4) . Y C7 N14 1.437(3) . Y C7 C8 1.540(3) . Y C8 O13 1.210(3) . Y C9 O11 1.243(3) . Y C9 O12 1.253(3) . Y N14 C15 1.333(3) . Y C15 O16 1.216(3) . Y C15 C17 1.523(3) . Y C17 N18 1.493(3) . Y C17 C19 1.513(3) . Y C19 C24 1.328(4) . Y C19 C20 1.485(4) . Y C20 C21 1.504(4) . Y C21 C22 1.304(6) . Y C22 C23 1.470(6) . Y C23 C24 1.496(5) . Y C30 C31 1.379(8) . Y C30 C39 1.406(10) . Y C30 C40 1.510(11) . Y C30 C34 2.009(15) 2_656 Y C31 C32 1.421(9) . Y C32 C33 1.403(10) . Y C32 C37 1.406(11) . Y C32 C32 1.977(18) 2_656 Y C33 C34 1.385(11) . Y C34 C35 1.387(12) . Y C34 C30 2.009(15) 2_656 Y C35 C36 1.386(13) . Y C35 C37 2.007(13) 2_656 Y C36 C37 1.390(10) . Y C37 C38 1.400(11) . Y C37 C35 2.007(13) 2_656 Y C38 C39 1.387(13) . Y C40 O41 1.206(8) . Y C40 C41 1.57(3) . Y 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 C6 S1 C2 94.86(12) . . Y C3 C2 S1 117.36(17) . . Y C4 C3 C10 123.4(2) . . Y C4 C3 C2 124.1(2) . . Y C10 C3 C2 112.5(2) . . Y C3 C4 N5 119.34(19) . . Y C3 C4 C9 125.06(19) . . Y N5 C4 C9 115.25(18) . . Y C8 N5 C4 134.1(2) . . Y C8 N5 C6 95.40(17) . . Y C4 N5 C6 126.26(18) . . Y N5 C6 C7 87.67(17) . . Y N5 C6 S1 110.90(17) . . Y C7 C6 S1 116.38(18) . . Y N14 C7 C8 113.9(2) . . Y N14 C7 C6 118.7(2) . . Y C8 C7 C6 84.82(16) . . Y O13 C8 N5 133.32(19) . . Y O13 C8 C7 134.8(2) . . Y N5 C8 C7 91.83(18) . . Y O11 C9 O12 125.4(2) . . Y O11 C9 C4 118.7(2) . . Y O12 C9 C4 115.8(2) . . Y C15 N14 C7 121.1(2) . . Y O16 C15 N14 122.8(2) . . Y O16 C15 C17 121.78(17) . . Y N14 C15 C17 115.5(2) . . Y N18 C17 C19 111.86(16) . . Y N18 C17 C15 106.9(2) . . Y C19 C17 C15 113.02(18) . . Y C24 C19 C20 122.9(2) . . Y C24 C19 C17 119.0(2) . . Y C20 C19 C17 118.0(2) . . Y C19 C20 C21 112.6(3) . . Y C22 C21 C20 124.2(3) . . Y C21 C22 C23 123.4(3) . . Y C22 C23 C24 113.4(4) . . Y C19 C24 C23 123.4(3) . . Y C31 C30 C39 118.8(8) . . Y C31 C30 C40 120.9(6) . . Y C39 C30 C40 120.3(7) . . Y C31 C30 C34 100.0(7) . 2_656 Y C39 C30 C34 18.9(5) . 2_656 Y C40 C30 C34 139.1(6) . 2_656 Y C30 C31 C32 121.8(7) . . Y C33 C32 C37 120.9(9) . . Y C33 C32 C31 120.5(7) . . Y C37 C32 C31 118.6(8) . . Y C33 C32 C32 102.3(7) . 2_656 Y C37 C32 C32 18.7(5) . 2_656 Y C31 C32 C32 137.1(8) . 2_656 Y C34 C33 C32 118.8(11) . . Y C33 C34 C35 121.4(12) . . Y C33 C34 C30 139.9(11) . 2_656 Y C35 C34 C30 19.0(6) . 2_656 Y C36 C35 C34 118.9(10) . . Y C36 C35 C37 56.6(6) . 2_656 Y C34 C35 C37 62.4(7) . 2_656 Y C35 C36 C37 122.0(11) . . Y C36 C37 C38 122.6(9) . . Y C36 C37 C32 118.0(10) . . Y C38 C37 C32 119.4(9) . . Y C36 C37 C35 178.4(9) . 2_656 Y C38 C37 C35 56.0(6) . 2_656 Y C32 C37 C35 63.5(6) . 2_656 Y C39 C38 C37 120.9(8) . . Y C38 C39 C30 120.4(8) . . Y O41 C40 C30 118.0(8) . . Y O41 C40 C41 121.7(11) . . Y C30 C40 C41 120.3(10) . . Y _diffrn_reflns_theta_full 69.88 _refine_diff_density_max 0.240 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.037 _publ_section_experimental ; Crystal colour: transparent colourless, crystal shape: regular thick needle. Profile analysis combining the methods of Lehman & Larsen (1974) and Grant & Gabe (1978). Empirical absorption correction using EMPABS (North, Phillips & Mathews, 1968). Data collection parameters: \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.48 + 0.17tan\q)\%, range: 0.74\%-1.43\%, aperture (1.51 + 0.09tan\q)mm., range: 1.52-1.75mm. Maximum scan time: 30 sec/reflection. Least-squares refinement using calculated weights: w=1/[\s^2^(Fo^2^)+(0.0697P)^2^+0.4696P] where P=(Fo^2^+2Fc^2^)/3 ; #===END data_CODI27 # 1. SUBMISSION DETAILS _publ_contact_autor ; Dr. R. de Gelder Crystallography Department University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; _publ_contact_author_phone '031 024 3652842' _publ_contact_author_fax '031 024 3553450' _publ_contact_author_email rdg@sci.kun.nl _publ_requested_journal 'Perkin Transactions 2' _publ_requested_coeditor_name ? _publ_contact_letter ; ; #============================================================================== # 3. AUTHOR LIST loop_ _publ_author_name _publ_author_address 'G.J. Kemperman' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'R. de Gelder' ; Department of Inorganic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'F.J. Dommerholt' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'P.C. Raemakers-Franken' ; DSM Research Department of Organic Chemistry and Biotechnology P.O. Box 18 6160 MD Geleen The Netherlands ; 'A.J.H. Klunder' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'B. Zwanenburg' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; #============================================================================== # 4. TEXT _publ_section_title ; Induced Fit Phenomena in Clathrate Structures of Cephalosporins ; _publ_section_abstract ; ; _publ_section_references ; Beurskens, P. T., Beurskens, G., Bosman, W. P., Gelder, R. de, Garc\'ia-Granda, S., Gould, R. O., Isra\"el, R. & Smits, J. M. M. (1996). DIRDIF-96, A computer program system for crystal structure determination by Patterson methods and direct methods applied to difference structure factors. Crystallography Laboratory, University of Nijmegen, The Netherlands. Beurskens, P. T., Beurskens, G., Strumpel, M. & Nordman, C. E. (1987). In Patterson and Pattersons, pp. 356--367. Glusker, J. P., Patterson, B. K. & Rossi, M., Eds. Oxford, England: Clarendon Press. CAD4 EXPRESS Enraf-Nonius diffractometer control software (1994). Release 5.1, Enraf-Nonius Delft, The Netherlands. Grant, D. F. & Gabe, E. J. (1978). J. Appl. Cryst. 11, 114--120. International Tables for X-ray Crystallography (1974). Vol. IV, Birmingham, England: Kynoch Press. Lehman, M. S. & Larsen, F. K. (1974). Acta Cryst. A30, 580--584. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351--359. Sheldrick, G. M. (1997). SHELXL-97, Program for the refinement of crystal structures. University of G\"ottingen, Germany. Smits, J. M. M., Behm, H., Bosman, W. P. & Beurskens, P. T. (1988). J. Crystallogr. Spectrosc. Res. 18, 447--450. Spek, A. L. (1990). Acta Cryst. A46, C-34. Spek, A. L. (1993). PLUTON, A program for plotting molecular and crystal structures. University of Utrecht, The Netherlands. Spek, A. L. (1995). PLATON-93, Program for display and analysis of crystal and molecular structures. University of Utrecht, The Netherlands. ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #============================================================================== _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 1999-05-04 _chemical_name_systematic ; Cefadroxil/2,7-dihydroxynaphthalene ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H56 N6 O19 S2' _chemical_formula_weight 1013.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 7.0902(7) _cell_length_b 21.273(3) _cell_length_c 31.004(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4676.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 208(2) _cell_measurement_reflns_used 15 _cell_measurement_theta_min 20.890 _cell_measurement_theta_max 23.058 _exptl_crystal_description 'regular thin needle' _exptl_crystal_colour 'transparent colourless' _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2136 _exptl_absorpt_coefficient_mu 1.759 _exptl_absorpt_correction_type experimental #_exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_T_max 1.033 _exptl_special_details ; ? ; _diffrn_ambient_temperature 208(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius CAD4' _diffrn_measurement_method \w/2\q-scan _diffrn_special_details ; \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.53 + 0.22tan\q)\%, range: 0.81\%-1.72\%, aperture (1.50 + 0.25tan\q)mm., range: 1.51-2.19mm. Maximum scan time: 30 sec/reflection. ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_time 7200 _diffrn_standards_decay_% 5.832 _diffrn_reflns_number 5017 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 70.05 _reflns_number_total 5017 _reflns_number_gt 3705 _reflns_number_observed 3705 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; CAD4 EXPRESS (Enraf-Nonius, 1994) ; #_computing_cell_refinement #; #CAD4 EXPRESS (Enraf-Nonius, 1994) #; _computing_data_reduction ; local programs (Smits et al., 1988), profile analysis (Lehman & Larsen, 1974, Grant & Gabe, 1978), EMPABS (North et al., 1968) ; _computing_structure_solution ; DIRDIF (Beurskens et al., 1996), PATTY (Beurskens et al., 1987) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLUTON (Spek, 1993), PLATON (Spek, 1990, 1995) ; _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 ; w=1/[\s^2^(Fo^2^)+(0.1866P)^2^+10.9705P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack -0.12(6) _refine_ls_number_reflns 5017 _refine_ls_number_parameters 630 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1394 _refine_ls_R_factor_gt 0.1085 _refine_ls_R_factor_obs 0.1085 _refine_ls_wR_factor_ref 0.3064 _refine_ls_wR_factor_all 0.3064 _refine_ls_wR_factor_gt 0.2737 _refine_ls_wR_factor_obs 0.2737 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_goodness_of_fit_all 1.092 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_shift/esd_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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1A S -0.0110(4) -0.21051(10) 0.35630(7) 0.0346(5) Uani 1 d . . . C2A C -0.0691(15) -0.1273(4) 0.3604(3) 0.038(2) Uani 1 d . . . H2A H -0.1894 -0.1233 0.3758 0.045 Uiso 1 calc R . . H2B H 0.0276 -0.1067 0.3781 0.045 Uiso 1 calc R . . C3A C -0.0848(14) -0.0918(4) 0.3180(3) 0.033(2) Uani 1 d . . . C4A C -0.1172(16) -0.1187(4) 0.2798(3) 0.036(2) Uani 1 d . . . N5A N -0.1483(12) -0.1850(3) 0.2783(2) 0.0320(17) Uani 1 d . . . C6A C -0.1816(14) -0.2268(4) 0.3145(3) 0.0301(19) Uani 1 d . . . H6A H -0.3139 -0.2271 0.3247 0.036 Uiso 1 calc R . . C7A C -0.1320(14) -0.2817(4) 0.2837(3) 0.032(2) Uani 1 d . . . H7A H -0.2455 -0.3061 0.2756 0.038 Uiso 1 calc R . . C8A C -0.0888(14) -0.2310(4) 0.2506(3) 0.034(2) Uani 1 d . . . C9A C -0.1405(17) -0.0856(4) 0.2381(3) 0.041(2) Uani 1 d . . . C10A C -0.0757(18) -0.0211(4) 0.3249(4) 0.048(3) Uani 1 d . . . H10A H -0.1760 -0.0083 0.3443 0.072 Uiso 1 calc R . . H10B H -0.0906 0.0002 0.2974 0.072 Uiso 1 calc R . . H10C H 0.0453 -0.0100 0.3374 0.072 Uiso 1 calc R . . O11A O -0.0328(13) -0.0399(3) 0.2298(3) 0.055(2) Uani 1 d . . . O12A O -0.2683(15) -0.1046(4) 0.2137(2) 0.062(3) Uani 1 d . . . O13A O -0.0252(15) -0.2296(3) 0.2145(2) 0.054(2) Uani 1 d . . . N14A N 0.0249(12) -0.3224(3) 0.2941(2) 0.0326(17) Uani 1 d . . . H14A H 0.1388 -0.3098 0.2882 0.039 Uiso 1 calc R . . C15A C 0.0012(15) -0.3781(4) 0.3123(3) 0.0326(19) Uani 1 d . . . O16A O -0.1511(11) -0.4038(3) 0.3177(3) 0.049(2) Uani 1 d . . . C17A C 0.1844(16) -0.4098(5) 0.3272(3) 0.040(2) Uani 1 d . . . H17A H 0.2739 -0.4116 0.3027 0.048 Uiso 1 calc R . . N18A N 0.1341(18) -0.4757(4) 0.3408(3) 0.064(3) Uani 1 d . . . H18A H 0.2369 -0.4948 0.3517 0.096 Uiso 1 calc R . . H18B H 0.0922 -0.4974 0.3178 0.096 Uiso 1 calc R . . H18C H 0.0433 -0.4743 0.3610 0.096 Uiso 1 calc R . . C19A C 0.2738(14) -0.3754(4) 0.3637(3) 0.032(2) Uani 1 d . . . C20A C 0.1683(16) -0.3564(4) 0.3992(3) 0.037(2) Uani 1 d . . . H20A H 0.0375 -0.3637 0.3997 0.045 Uiso 1 calc R . . C21A C 0.2547(15) -0.3266(5) 0.4342(3) 0.039(2) Uani 1 d . . . H21A H 0.1823 -0.3139 0.4580 0.046 Uiso 1 calc R . . C22A C 0.4494(14) -0.3158(4) 0.4336(3) 0.032(2) Uani 1 d . . . C23A C 0.5526(14) -0.3330(5) 0.3975(3) 0.041(2) Uani 1 d . . . H23A H 0.6828 -0.3249 0.3964 0.049 Uiso 1 calc R . . C24A C 0.4635(13) -0.3622(5) 0.3630(3) 0.038(2) Uani 1 d . . . H24A H 0.5348 -0.3731 0.3386 0.046 Uiso 1 calc R . . O25A O 0.5385(11) -0.2891(4) 0.4675(2) 0.0476(18) Uani 1 d . . . H25A H 0.4718 -0.2924 0.4894 0.071 Uiso 1 calc R . . S1B S 0.5189(5) -0.08447(12) 0.91826(8) 0.0513(8) Uani 1 d . . . C2B C 0.5792(19) -0.0135(5) 0.9465(3) 0.050(3) Uani 1 d . . . H2C H 0.7027 0.0002 0.9359 0.060 Uiso 1 calc R . . H2D H 0.4878 0.0187 0.9380 0.060 Uiso 1 calc R . . C3B C 0.588(2) -0.0140(5) 0.9953(3) 0.052(3) Uani 1 d . . . C4B C 0.598(2) -0.0669(5) 1.0205(3) 0.054(3) Uani 1 d . . . N5B N 0.5950(18) -0.1246(4) 0.9997(3) 0.053(3) Uani 1 d . . . C6B C 0.635(2) -0.1385(5) 0.9532(3) 0.047(3) Uani 1 d . . . H6B H 0.7714 -0.1433 0.9468 0.056 Uiso 1 calc R . . C7B C 0.533(2) -0.2021(5) 0.9612(4) 0.053(3) Uani 1 d . . . H7B H 0.6183 -0.2388 0.9605 0.064 Uiso 1 calc R . . C8B C 0.496(2) -0.1783(5) 1.0058(4) 0.056(3) Uani 1 d . . . C9B C 0.639(2) -0.0677(6) 1.0692(3) 0.053(3) Uani 1 d . . . C10B C 0.592(3) 0.0519(5) 1.0133(4) 0.072(5) Uani 1 d . . . H10D H 0.4658 0.0692 1.0134 0.108 Uiso 1 calc R . . H10E H 0.6736 0.0779 0.9956 0.108 Uiso 1 calc R . . H10F H 0.6407 0.0509 1.0426 0.108 Uiso 1 calc R . . O11B O 0.5736(19) -0.0227(5) 1.0915(3) 0.083(3) Uani 1 d . . . O12B O 0.7327(16) -0.1087(4) 1.0828(3) 0.063(2) Uani 1 d . . . O13B O 0.4071(16) -0.1981(4) 1.0373(2) 0.063(2) Uani 1 d . . . N14B N 0.3586(17) -0.2119(4) 0.9368(3) 0.055(3) Uani 1 d . . . H14B H 0.2555 -0.1942 0.9460 0.066 Uiso 1 calc R . . C15B C 0.3511(19) -0.2466(5) 0.9012(3) 0.048(3) Uani 1 d . . . O16B O 0.4905(16) -0.2755(4) 0.8867(2) 0.067(3) Uani 1 d . . . C17B C 0.163(2) -0.2521(5) 0.8791(3) 0.050(3) Uani 1 d . . . H17B H 0.0658 -0.2569 0.9017 0.060 Uiso 1 calc R . . N18B N 0.1614(18) -0.3115(5) 0.8519(3) 0.058(3) Uani 1 d . . . H18D H 0.0414 -0.3225 0.8462 0.087 Uiso 1 calc R . . H18E H 0.2187 -0.3428 0.8664 0.087 Uiso 1 calc R . . H18F H 0.2231 -0.3045 0.8270 0.087 Uiso 1 calc R . . C19B C 0.1068(19) -0.1972(5) 0.8514(4) 0.053(3) Uani 1 d . . . C20B C 0.234(2) -0.1611(5) 0.8294(3) 0.050(3) Uani 1 d . . . H20B H 0.3636 -0.1684 0.8341 0.060 Uiso 1 calc R . . C21B C 0.1829(18) -0.1144(5) 0.8006(3) 0.046(3) Uani 1 d . . . H21B H 0.2753 -0.0909 0.7860 0.055 Uiso 1 calc R . . C22B C -0.0081(19) -0.1029(5) 0.7935(3) 0.046(3) Uani 1 d . . . C23B C -0.1427(19) -0.1376(5) 0.8156(4) 0.059(4) Uani 1 d . . . H23B H -0.2714 -0.1288 0.8115 0.071 Uiso 1 calc R . . C24B C -0.088(2) -0.1853(6) 0.8440(4) 0.068(4) Uani 1 d . . . H24B H -0.1804 -0.2095 0.8581 0.082 Uiso 1 calc R . . O25B O -0.0712(12) -0.0588(3) 0.7654(2) 0.0477(18) Uani 1 d . . . H25B H 0.0198 -0.0390 0.7554 0.071 Uiso 1 calc R . . C30 C -0.580(2) 0.0457(5) 0.4556(4) 0.057(3) Uani 1 d . . . O30 O -0.5854(16) 0.1077(3) 0.4663(3) 0.065(3) Uani 1 d . . . H30 H -0.5558 0.1119 0.4921 0.098 Uiso 1 calc R . . C31 C -0.588(2) -0.0006(6) 0.4869(4) 0.061(4) Uani 1 d . . . H31 H -0.5952 0.0110 0.5161 0.073 Uiso 1 calc R . . O31 O -0.5830(12) -0.1354(3) 0.3031(3) 0.0511(19) Uani 1 d . . . H31A H -0.6071 -0.1056 0.2867 0.077 Uiso 1 calc R . . C32 C -0.586(2) -0.0631(6) 0.4761(4) 0.061(4) Uani 1 d . . . H32 H -0.5866 -0.0939 0.4978 0.073 Uiso 1 calc R . . C33 C -0.5815(17) -0.0808(5) 0.4329(4) 0.047(3) Uani 1 d . . . C34 C -0.5729(17) -0.0334(5) 0.3995(4) 0.048(3) Uani 1 d . . . C35 C -0.5705(18) 0.0295(5) 0.4131(4) 0.051(3) Uani 1 d . . . H35 H -0.5624 0.0615 0.3922 0.061 Uiso 1 calc R . . C36 C -0.5779(14) -0.1147(5) 0.3445(4) 0.043(2) Uani 1 d . . . C37 C -0.5842(15) -0.1619(5) 0.3784(4) 0.046(3) Uani 1 d . . . H37 H -0.5895 -0.2047 0.3709 0.055 Uiso 1 calc R . . C38 C -0.5827(18) -0.1455(5) 0.4203(4) 0.051(3) Uani 1 d . . . H38 H -0.5824 -0.1770 0.4416 0.061 Uiso 1 calc R . . C39 C -0.5746(16) -0.0525(4) 0.3571(4) 0.043(2) Uani 1 d . . . H39 H -0.5735 -0.0214 0.3356 0.052 Uiso 1 calc R . . O40 O -0.6251(12) -0.2590(4) 0.2708(3) 0.054(2) Uani 1 d . . . O50 O -0.1422(15) -0.2282(7) 0.4585(3) 0.096(4) Uani 1 d . . . O60 O -0.6603(16) -0.0396(4) 0.2481(3) 0.067(3) Uani 1 d . . . O70 O -0.417(2) -0.3802(5) -0.0533(3) 0.098(4) Uani 1 d . . . O80 O -0.720(2) -0.1609(8) 0.1762(5) 0.152(7) Uani 1 d . . . O90 O -0.176(3) -0.4995(13) 0.3985(7) 0.226(13) Uani 1 d . . . O100 O 0.047(3) 0.0361(16) 0.6694(6) 0.262(16) Uani 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 S1A 0.0377(12) 0.0321(10) 0.0340(10) -0.0012(8) -0.0095(11) 0.0064(10) C2A 0.036(5) 0.033(4) 0.044(5) -0.009(4) -0.009(5) 0.006(4) C3A 0.030(5) 0.029(4) 0.040(5) -0.005(4) -0.004(4) -0.002(4) C4A 0.050(6) 0.020(4) 0.038(5) 0.008(4) -0.014(5) 0.001(4) N5A 0.041(4) 0.026(3) 0.029(3) 0.003(3) -0.013(3) 0.000(3) C6A 0.038(5) 0.023(4) 0.029(4) 0.001(3) 0.001(4) 0.011(4) C7A 0.029(5) 0.027(4) 0.039(5) 0.000(4) -0.012(4) 0.003(4) C8A 0.033(5) 0.031(4) 0.039(5) -0.001(4) -0.010(4) -0.001(4) C9A 0.060(7) 0.020(4) 0.044(5) 0.000(4) -0.022(5) -0.009(5) C10A 0.057(7) 0.030(5) 0.057(6) -0.011(4) -0.030(6) 0.008(5) O11A 0.066(6) 0.037(4) 0.062(5) 0.013(3) -0.020(5) -0.021(4) O12A 0.087(7) 0.050(4) 0.050(4) 0.011(4) -0.037(5) -0.025(5) O13A 0.085(6) 0.041(4) 0.037(4) 0.002(3) -0.011(4) -0.015(4) N14A 0.026(4) 0.027(3) 0.045(4) 0.003(3) -0.002(4) -0.002(3) C15A 0.035(5) 0.026(4) 0.036(4) -0.002(3) -0.002(5) 0.006(4) O16A 0.034(4) 0.033(4) 0.079(5) 0.014(4) 0.006(4) 0.002(3) C17A 0.041(6) 0.041(5) 0.039(5) -0.011(4) -0.006(5) 0.016(5) N18A 0.087(8) 0.032(4) 0.073(7) -0.008(4) -0.041(7) 0.018(5) C19A 0.033(5) 0.027(4) 0.035(5) -0.001(4) 0.000(4) 0.005(4) C20A 0.041(5) 0.037(5) 0.034(5) -0.005(4) 0.001(5) 0.005(5) C21A 0.030(5) 0.052(6) 0.034(5) -0.001(4) 0.000(4) 0.000(5) C22A 0.032(5) 0.033(4) 0.032(4) 0.000(4) -0.002(4) -0.005(4) C23A 0.018(4) 0.052(6) 0.052(6) -0.010(5) 0.007(4) -0.002(4) C24A 0.019(4) 0.057(6) 0.038(5) -0.003(4) -0.004(4) 0.005(4) O25A 0.043(4) 0.059(4) 0.041(4) -0.007(3) -0.009(3) -0.011(4) S1B 0.072(2) 0.0381(12) 0.0442(13) 0.0079(10) 0.0134(15) 0.0068(14) C2B 0.068(8) 0.040(5) 0.041(5) 0.017(4) 0.022(6) 0.012(6) C3B 0.082(9) 0.030(5) 0.043(6) 0.008(4) 0.018(6) 0.011(6) C4B 0.083(9) 0.038(5) 0.042(6) -0.003(5) 0.013(6) 0.004(6) N5B 0.088(8) 0.031(4) 0.040(4) 0.012(4) 0.017(5) 0.007(5) C6B 0.067(7) 0.035(5) 0.038(5) 0.006(4) 0.009(6) 0.008(6) C7B 0.072(9) 0.035(5) 0.052(6) 0.005(5) 0.008(6) 0.021(6) C8B 0.079(9) 0.037(5) 0.052(6) 0.020(5) 0.015(7) 0.004(7) C9B 0.063(8) 0.056(6) 0.038(5) -0.002(5) -0.004(6) 0.011(7) C10B 0.117(14) 0.032(5) 0.066(8) 0.000(5) 0.028(9) 0.009(8) O11B 0.109(9) 0.077(6) 0.062(5) 0.001(5) 0.004(6) 0.009(7) O12B 0.094(7) 0.053(5) 0.041(4) 0.015(4) -0.002(5) -0.004(5) O13B 0.089(7) 0.051(4) 0.048(4) 0.019(4) 0.007(5) -0.009(5) N14B 0.071(7) 0.038(4) 0.055(5) 0.003(4) 0.027(6) 0.014(5) C15B 0.066(8) 0.040(5) 0.038(5) 0.005(4) 0.017(6) 0.011(6) O16B 0.099(7) 0.060(5) 0.041(4) -0.001(4) 0.012(5) 0.035(6) C17B 0.079(9) 0.036(5) 0.036(5) 0.008(4) 0.022(6) 0.008(6) N18B 0.082(8) 0.056(5) 0.035(4) -0.004(4) 0.000(5) 0.023(6) C19B 0.057(7) 0.048(6) 0.054(6) 0.007(5) 0.012(6) 0.032(6) C20B 0.069(8) 0.044(6) 0.037(5) 0.010(5) 0.021(6) 0.030(6) C21B 0.060(7) 0.036(5) 0.041(5) 0.006(4) 0.010(5) 0.022(5) C22B 0.059(7) 0.038(5) 0.041(5) 0.011(4) 0.004(6) 0.019(6) C23B 0.052(7) 0.050(6) 0.076(8) 0.036(6) 0.018(7) 0.023(6) C24B 0.084(10) 0.046(6) 0.076(9) 0.030(6) 0.041(8) 0.014(7) O25B 0.052(5) 0.038(4) 0.053(4) 0.012(3) 0.003(4) 0.011(4) C30 0.074(9) 0.037(5) 0.061(7) -0.007(5) -0.040(7) 0.015(6) O30 0.085(7) 0.034(4) 0.077(6) -0.018(4) -0.038(6) 0.018(4) C31 0.080(10) 0.055(7) 0.049(6) -0.004(5) -0.026(7) 0.022(7) O31 0.047(4) 0.042(4) 0.064(5) -0.011(4) -0.010(4) 0.006(4) C32 0.074(9) 0.051(6) 0.057(7) -0.003(6) -0.038(7) 0.017(7) C33 0.040(6) 0.040(5) 0.060(6) 0.002(5) -0.018(5) 0.009(5) C34 0.047(6) 0.046(6) 0.051(6) 0.000(5) -0.026(5) 0.011(5) C35 0.062(8) 0.036(5) 0.054(6) 0.003(5) -0.031(6) 0.011(5) C36 0.019(4) 0.044(5) 0.066(7) -0.007(5) -0.009(5) 0.004(4) C37 0.026(5) 0.031(5) 0.080(8) -0.005(5) -0.011(5) 0.007(4) C38 0.054(7) 0.037(5) 0.061(7) -0.004(5) -0.023(6) 0.012(5) C39 0.047(6) 0.030(4) 0.054(6) -0.004(4) -0.025(5) 0.007(4) O40 0.043(4) 0.054(5) 0.064(5) -0.014(4) -0.004(4) -0.008(4) O50 0.059(6) 0.186(12) 0.043(5) 0.001(6) 0.006(5) -0.040(8) O60 0.085(7) 0.066(5) 0.052(5) -0.013(4) -0.004(5) -0.018(5) O70 0.137(11) 0.079(6) 0.076(6) 0.042(5) -0.039(8) -0.030(7) O80 0.128(12) 0.202(16) 0.124(10) -0.095(11) 0.053(10) -0.090(13) O90 0.097(12) 0.37(3) 0.21(2) 0.17(2) 0.034(13) 0.055(17) O100 0.158(19) 0.49(5) 0.135(14) 0.11(2) -0.007(14) -0.12(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 S1A C6A 1.806(9) . Y S1A C2A 1.823(9) . Y C2A C3A 1.520(13) . Y C3A C4A 1.336(13) . Y C3A C10A 1.521(12) . Y C4A N5A 1.429(11) . Y C4A C9A 1.482(13) . Y N5A C8A 1.367(12) . Y N5A C6A 1.452(11) . Y C6A C7A 1.550(12) . Y C7A N14A 1.447(12) . Y C7A C8A 1.519(13) . Y C8A O13A 1.207(12) . Y C9A O12A 1.247(13) . Y C9A O11A 1.263(12) . Y N14A C15A 1.323(11) . Y C15A O16A 1.223(13) . Y C15A C17A 1.534(14) . Y C17A C19A 1.488(14) . Y C17A N18A 1.507(15) . Y C19A C24A 1.375(14) . Y C19A C20A 1.393(13) . Y C20A C21A 1.397(14) . Y C21A C22A 1.400(14) . Y C22A O25A 1.350(11) . Y C22A C23A 1.386(13) . Y C23A C24A 1.390(14) . Y S1B C6B 1.781(11) . Y S1B C2B 1.796(12) . Y C2B C3B 1.516(15) . Y C3B C4B 1.371(15) . Y C3B C10B 1.509(15) . Y C4B N5B 1.386(14) . Y C4B C9B 1.540(15) . Y N5B C8B 1.355(16) . Y N5B C6B 1.499(13) . Y C6B C7B 1.558(16) . Y C7B N14B 1.462(18) . Y C7B C8B 1.496(15) . Y C8B O13B 1.234(14) . Y C9B O12B 1.176(15) . Y C9B O11B 1.268(15) . Y N14B C15B 1.330(14) . Y C15B O16B 1.248(15) . Y C15B C17B 1.504(19) . Y C17B C19B 1.503(15) . Y C17B N18B 1.520(14) . Y C19B C20B 1.369(17) . Y C19B C24B 1.43(2) . Y C20B C21B 1.385(14) . Y C21B C22B 1.393(18) . Y C22B O25B 1.358(11) . Y C22B C23B 1.387(17) . Y C23B C24B 1.397(16) . Y C30 O30 1.361(12) . Y C30 C35 1.364(16) . Y C30 C31 1.384(17) . Y C31 C32 1.371(17) . Y O31 C36 1.359(13) . Y C32 C33 1.390(16) . Y C33 C38 1.432(14) . Y C33 C34 1.446(15) . Y C34 C39 1.376(15) . Y C34 C35 1.404(15) . Y C36 C39 1.380(14) . Y C36 C37 1.456(16) . Y C37 C38 1.345(16) . Y 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 C6A S1A C2A 94.9(4) . . Y C3A C2A S1A 115.9(7) . . Y C4A C3A C2A 124.6(8) . . Y C4A C3A C10A 123.7(9) . . Y C2A C3A C10A 111.5(8) . . Y C3A C4A N5A 118.5(8) . . Y C3A C4A C9A 126.2(8) . . Y N5A C4A C9A 115.0(8) . . Y C8A N5A C4A 132.8(9) . . Y C8A N5A C6A 95.6(7) . . Y C4A N5A C6A 127.2(7) . . Y N5A C6A C7A 86.9(6) . . Y N5A C6A S1A 109.2(6) . . Y C7A C6A S1A 115.8(6) . . Y N14A C7A C8A 114.9(8) . . Y N14A C7A C6A 119.2(7) . . Y C8A C7A C6A 85.8(7) . . Y O13A C8A N5A 132.8(9) . . Y O13A C8A C7A 135.9(9) . . Y N5A C8A C7A 91.3(7) . . Y O12A C9A O11A 124.5(9) . . Y O12A C9A C4A 117.2(9) . . Y O11A C9A C4A 118.3(9) . . Y C15A N14A C7A 122.3(9) . . Y O16A C15A N14A 124.9(9) . . Y O16A C15A C17A 120.6(8) . . Y N14A C15A C17A 114.5(9) . . Y C19A C17A N18A 110.2(9) . . Y C19A C17A C15A 112.0(8) . . Y N18A C17A C15A 107.0(9) . . Y C24A C19A C20A 118.6(10) . . Y C24A C19A C17A 120.4(9) . . Y C20A C19A C17A 121.0(9) . . Y C19A C20A C21A 120.7(10) . . Y C20A C21A C22A 119.9(10) . . Y O25A C22A C23A 119.4(9) . . Y O25A C22A C21A 121.4(9) . . Y C23A C22A C21A 119.1(9) . . Y C22A C23A C24A 120.0(9) . . Y C19A C24A C23A 121.6(10) . . Y C6B S1B C2B 97.8(5) . . Y C3B C2B S1B 119.4(7) . . Y C4B C3B C10B 123.5(10) . . Y C4B C3B C2B 125.2(10) . . Y C10B C3B C2B 111.3(9) . . Y C3B C4B N5B 117.5(9) . . Y C3B C4B C9B 125.3(10) . . Y N5B C4B C9B 116.7(10) . . Y C8B N5B C4B 133.5(11) . . Y C8B N5B C6B 93.9(9) . . Y C4B N5B C6B 128.1(8) . . Y N5B C6B C7B 85.9(8) . . Y N5B C6B S1B 111.7(7) . . Y C7B C6B S1B 116.2(10) . . Y N14B C7B C8B 112.2(11) . . Y N14B C7B C6B 115.8(9) . . Y C8B C7B C6B 86.3(8) . . Y O13B C8B N5B 131.5(11) . . Y O13B C8B C7B 134.7(12) . . Y N5B C8B C7B 93.7(9) . . Y O12B C9B O11B 124.9(11) . . Y O12B C9B C4B 117.7(11) . . Y O11B C9B C4B 117.3(11) . . Y C15B N14B C7B 122.8(10) . . Y O16B C15B N14B 122.8(13) . . Y O16B C15B C17B 119.9(10) . . Y N14B C15B C17B 117.2(11) . . Y C19B C17B C15B 115.9(11) . . Y C19B C17B N18B 109.1(9) . . Y C15B C17B N18B 108.9(10) . . Y C20B C19B C24B 117.5(10) . . Y C20B C19B C17B 123.0(12) . . Y C24B C19B C17B 119.2(12) . . Y C19B C20B C21B 123.3(12) . . Y C20B C21B C22B 118.9(11) . . Y O25B C22B C23B 117.3(11) . . Y O25B C22B C21B 122.8(11) . . Y C23B C22B C21B 119.9(10) . . Y C22B C23B C24B 120.5(13) . . Y C23B C24B C19B 119.9(12) . . Y O30 C30 C35 118.9(11) . . Y O30 C30 C31 121.1(11) . . Y C35 C30 C31 119.9(10) . . Y C32 C31 C30 121.3(12) . . Y C31 C32 C33 119.9(12) . . Y C32 C33 C38 121.6(11) . . Y C32 C33 C34 120.1(10) . . Y C38 C33 C34 118.3(10) . . Y C39 C34 C35 124.6(10) . . Y C39 C34 C33 118.6(10) . . Y C35 C34 C33 116.8(10) . . Y C30 C35 C34 122.0(11) . . Y O31 C36 C39 125.5(10) . . Y O31 C36 C37 117.2(9) . . Y C39 C36 C37 117.2(10) . . Y C38 C37 C36 121.2(10) . . Y C37 C38 C33 120.9(11) . . Y C34 C39 C36 123.6(10) . . Y _diffrn_reflns_theta_full 70.05 _refine_diff_density_max 0.977 _refine_diff_density_min -0.839 _refine_diff_density_rms 0.130 _publ_section_experimental ; Crystal colour: transparent colourless, crystal shape: regular thin needle. Special experimental condition: measurements were performed at -65 degrees C. Profile analysis combining the methods of Lehman & Larsen (1974) and Grant & Gabe (1978). Empirical absorption correction using EMPABS (North, Phillips & Mathews, 1968). Data collection parameters: \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.53 + 0.22tan\q)\%, range: 0.81\%-1.72\%, aperture (1.50 + 0.25tan\q)mm., range: 1.51-2.19mm. Maximum scan time: 30 sec/reflection. Least-squares refinement using calculated weights: w=1/[\s^2^(Fo^2^)+(0.1866P)^2^+10.9705P] where P=(Fo^2^+2Fc^2^)/3 ; #===END data_CODI26 # 1. SUBMISSION DETAILS _publ_contact_autor ; Dr. R. de Gelder Crystallography Department University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; _publ_contact_author_phone '031 024 3652842' _publ_contact_author_fax '031 024 3553450' _publ_contact_author_email rdg@sci.kun.nl _publ_requested_journal 'Perkin Transactions 2' _publ_requested_coeditor_name ? _publ_contact_letter ; ; #============================================================================== # 3. AUTHOR LIST loop_ _publ_author_name _publ_author_address 'G.J. Kemperman' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'R. de Gelder' ; Department of Inorganic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'F.J. Dommerholt' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'P.C. Raemakers-Franken' ; DSM Research Department of Organic Chemistry and Biotechnology P.O. Box 18 6160 MD Geleen The Netherlands ; 'A.J.H. Klunder' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'B. Zwanenburg' ; Department of Organic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; #============================================================================== # 4. TEXT _publ_section_title ; Induced Fit Phenomena in Clathrate Structures of Cephalosporins ; _publ_section_abstract ; ; _publ_section_references ; Beurskens, P. T., Beurskens, G., Bosman, W. P., Gelder, R. de, Garc\'ia-Granda, S., Gould, R. O., Isra\"el, R. & Smits, J. M. M. (1996). DIRDIF-96, A computer program system for crystal structure determination by Patterson methods and direct methods applied to difference structure factors. Crystallography Laboratory, University of Nijmegen, The Netherlands. Beurskens, P. T., Beurskens, G., Strumpel, M. & Nordman, C. E. (1987). In Patterson and Pattersons, pp. 356--367. Glusker, J. P., Patterson, B. K. & Rossi, M., Eds. Oxford, England: Clarendon Press. CAD4 EXPRESS Enraf-Nonius diffractometer control software (1994). Release 5.1, Enraf-Nonius Delft, The Netherlands. Grant, D. F. & Gabe, E. J. (1978). J. Appl. Cryst. 11, 114--120. International Tables for X-ray Crystallography (1974). Vol. IV, Birmingham, England: Kynoch Press. Lehman, M. S. & Larsen, F. K. (1974). Acta Cryst. A30, 580--584. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351--359. Sheldrick, G. M. (1997). SHELXL-97, Program for the refinement of crystal structures. University of G\"ottingen, Germany. Smits, J. M. M., Behm, H., Bosman, W. P. & Beurskens, P. T. (1988). J. Crystallogr. Spectrosc. Res. 18, 447--450. Spek, A. L. (1990). Acta Cryst. A46, C-34. Spek, A. L. (1993). PLUTON, A program for plotting molecular and crystal structures. University of Utrecht, The Netherlands. Spek, A. L. (1995). PLATON-93, Program for display and analysis of crystal and molecular structures. University of Utrecht, The Netherlands. ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #============================================================================== _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 1999-05-04 _chemical_name_systematic ; Cefadroxil/2,6-dihydroxynaphthalene ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H60 N6 O21 S2' _chemical_formula_weight 1049.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 7.1079(18) _cell_length_b 21.863(5) _cell_length_c 32.306(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5020.4(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15 _cell_measurement_theta_min 18.122 _cell_measurement_theta_max 22.543 _exptl_crystal_description 'rather regular needle' _exptl_crystal_colour 'transparent colourless' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2216 _exptl_absorpt_coefficient_mu 1.687 _exptl_absorpt_correction_type experimental #_exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.987 _exptl_absorpt_correction_T_max 1.012 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius CAD4' _diffrn_measurement_method \w/2\q-scan _diffrn_special_details ; \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.50 + 0.19tan\q)\%, range: 0.77\%-1.55\%, aperture (1.52 + 0.16tan\q)mm., range: 1.53-1.95mm. Maximum scan time: 30 sec/reflection. ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_time 7200 _diffrn_standards_decay_% 4.346 _diffrn_reflns_number 5384 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0951 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 70.05 _reflns_number_total 5384 _reflns_number_gt 2881 _reflns_number_observed 2881 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; CAD4 EXPRESS (Enraf-Nonius, 1994) ; #_computing_cell_refinement #; #CAD4 EXPRESS (Enraf-Nonius, 1994) #; _computing_data_reduction ; local programs (Smits et al., 1988), profile analysis (Lehman & Larsen, 1974, Grant & Gabe, 1978), EMPABS (North et al., 1968) ; _computing_structure_solution ; DIRDIF (Beurskens et al., 1996), PATTY (Beurskens et al., 1987) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLUTON (Spek, 1993), PLATON (Spek, 1990, 1995) ; _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 ; w=1/[\s^2^(Fo^2^)+(0.1207P)^2^+0.0000P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack 0.03(6) _refine_ls_number_reflns 5384 _refine_ls_number_parameters 648 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1557 _refine_ls_R_factor_gt 0.0771 _refine_ls_R_factor_obs 0.0771 _refine_ls_wR_factor_ref 0.2369 _refine_ls_wR_factor_all 0.2369 _refine_ls_wR_factor_gt 0.1898 _refine_ls_wR_factor_obs 0.1898 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_goodness_of_fit_all 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_shift/esd_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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1A S -0.0107(4) -0.18384(12) -0.14667(7) 0.0541(7) Uani 1 d . . . C2A C -0.0690(15) -0.1037(4) -0.1422(3) 0.051(3) Uani 1 d . . . H2A H -0.1870 -0.1004 -0.1272 0.061 Uiso 1 calc R . . H2B H 0.0270 -0.0841 -0.1255 0.061 Uiso 1 calc R . . C3A C -0.0875(13) -0.0682(4) -0.1826(3) 0.046(2) Uani 1 d . . . C4A C -0.1181(15) -0.0937(4) -0.2195(3) 0.046(2) Uani 1 d . . . N5A N -0.1428(11) -0.1579(3) -0.2221(2) 0.0386(18) Uani 1 d . . . C6A C -0.1758(14) -0.1995(4) -0.1880(3) 0.044(2) Uani 1 d . . . H6A H -0.3072 -0.2009 -0.1788 0.053 Uiso 1 calc R . . C7A C -0.1206(14) -0.2526(4) -0.2175(3) 0.044(2) Uani 1 d . . . H7A H -0.2304 -0.2770 -0.2255 0.053 Uiso 1 calc R . . C8A C -0.0828(14) -0.2005(4) -0.2485(3) 0.043(2) Uani 1 d . . . C9A C -0.1430(18) -0.0596(5) -0.2601(3) 0.055(3) Uani 1 d . . . C10A C -0.0774(18) 0.0004(4) -0.1757(3) 0.063(3) Uani 1 d . . . H10A H -0.1477 0.0210 -0.1970 0.095 Uiso 1 calc R . . H10B H 0.0515 0.0135 -0.1768 0.095 Uiso 1 calc R . . H10C H -0.1296 0.0102 -0.1492 0.095 Uiso 1 calc R . . O11A O -0.0381(11) -0.0134(3) -0.2656(2) 0.064(2) Uani 1 d . . . O12A O -0.2621(14) -0.0790(4) -0.2844(2) 0.085(3) Uani 1 d . . . O13A O -0.0139(12) -0.1988(3) -0.28287(17) 0.0604(19) Uani 1 d . . . N14A N 0.0356(12) -0.2901(3) -0.2079(2) 0.049(2) Uani 1 d . . . H14A H 0.1469 -0.2759 -0.2121 0.058 Uiso 1 calc R . . C15A C 0.0182(15) -0.3453(4) -0.1928(3) 0.043(2) Uani 1 d . . . O16A O -0.1320(11) -0.3717(3) -0.1877(2) 0.067(2) Uani 1 d . . . C17A C 0.2007(15) -0.3767(4) -0.1807(3) 0.044(2) Uani 1 d . . . H17A H 0.2878 -0.3734 -0.2041 0.052 Uiso 1 calc R . . N18A N 0.1685(14) -0.4423(3) -0.1725(2) 0.059(2) Uani 1 d . . . H18A H 0.1201 -0.4599 -0.1949 0.089 Uiso 1 calc R . . H18B H 0.0888 -0.4464 -0.1514 0.089 Uiso 1 calc R . . H18C H 0.2772 -0.4602 -0.1662 0.089 Uiso 1 calc R . . C19A C 0.2960(13) -0.3476(4) -0.1428(3) 0.040(2) Uani 1 d . . . C20A C 0.1907(16) -0.3385(5) -0.1066(3) 0.052(3) Uani 1 d . . . H20A H 0.0631 -0.3479 -0.1060 0.062 Uiso 1 calc R . . C21A C 0.2801(15) -0.3154(5) -0.0715(3) 0.054(3) Uani 1 d . . . H21A H 0.2111 -0.3074 -0.0477 0.065 Uiso 1 calc R . . C22A C 0.4734(15) -0.3042(4) -0.0723(3) 0.053(3) Uani 1 d . . . C23A C 0.5709(16) -0.3121(5) -0.1082(4) 0.067(3) Uani 1 d . . . H23A H 0.6981 -0.3023 -0.1091 0.081 Uiso 1 calc R . . C24A C 0.4835(16) -0.3344(5) -0.1428(3) 0.063(3) Uani 1 d . . . H24A H 0.5533 -0.3406 -0.1668 0.075 Uiso 1 calc R . . O25A O 0.5654(13) -0.2854(3) -0.0372(2) 0.076(2) Uani 1 d . . . H25A H 0.5680 -0.2479 -0.0365 0.114 Uiso 1 calc R . . S1B S 0.4922(4) -0.07013(12) 0.42861(7) 0.0600(7) Uani 1 d . . . C2B C 0.5738(15) -0.0061(4) 0.4599(3) 0.053(3) Uani 1 d . . . H2C H 0.6950 0.0072 0.4494 0.063 Uiso 1 calc R . . H2D H 0.4865 0.0277 0.4565 0.063 Uiso 1 calc R . . C3B C 0.5933(15) -0.0197(4) 0.5059(3) 0.051(2) Uani 1 d . . . C4B C 0.6184(14) -0.0747(4) 0.5216(3) 0.041(2) Uani 1 d . . . N5B N 0.6326(11) -0.1261(3) 0.4955(2) 0.0401(18) Uani 1 d . . . C6B C 0.6513(14) -0.1260(4) 0.4505(2) 0.047(2) Uani 1 d . . . H6B H 0.7816 -0.1206 0.4413 0.056 Uiso 1 calc R . . C7B C 0.5894(14) -0.1931(4) 0.4509(3) 0.048(2) Uani 1 d . . . H7B H 0.6930 -0.2212 0.4447 0.058 Uiso 1 calc R . . C8B C 0.5628(15) -0.1834(4) 0.4970(3) 0.045(2) Uani 1 d . . . C9B C 0.6317(17) -0.0898(4) 0.5672(3) 0.047(2) Uani 1 d . . . C10B C 0.5954(19) 0.0391(5) 0.5324(4) 0.073(4) Uani 1 d . . . H10D H 0.6054 0.0283 0.5612 0.110 Uiso 1 calc R . . H10E H 0.4811 0.0615 0.5280 0.110 Uiso 1 calc R . . H10F H 0.7010 0.0639 0.5247 0.110 Uiso 1 calc R . . O11B O 0.4876(13) -0.0829(4) 0.5883(2) 0.074(2) Uani 1 d . . . O12B O 0.7847(11) -0.1079(3) 0.5800(2) 0.061(2) Uani 1 d . . . O13B O 0.5003(12) -0.2140(3) 0.52518(19) 0.0577(18) Uani 1 d . . . N14B N 0.4220(11) -0.2081(3) 0.4291(2) 0.050(2) Uani 1 d . . . H14B H 0.3176 -0.1919 0.4369 0.060 Uiso 1 calc R . . C15B C 0.4212(14) -0.2471(4) 0.3962(2) 0.041(2) Uani 1 d . . . O16B O 0.5608(10) -0.2716(4) 0.3826(2) 0.062(2) Uani 1 d . . . C17B C 0.2232(14) -0.2581(4) 0.3775(3) 0.041(2) Uani 1 d . . . H17B H 0.1326 -0.2634 0.4001 0.050 Uiso 1 calc R . . N18B N 0.2382(12) -0.3168(3) 0.3540(2) 0.046(2) Uani 1 d . . . H18D H 0.3386 -0.3155 0.3375 0.070 Uiso 1 calc R . . H18E H 0.1352 -0.3221 0.3387 0.070 Uiso 1 calc R . . H18F H 0.2498 -0.3478 0.3716 0.070 Uiso 1 calc R . . C19B C 0.1549(13) -0.2071(4) 0.3492(3) 0.039(2) Uani 1 d . . . C20B C 0.2799(15) -0.1746(4) 0.3247(3) 0.051(3) Uani 1 d . . . H20B H 0.4086 -0.1817 0.3267 0.062 Uiso 1 calc R . . C21B C 0.2117(17) -0.1316(5) 0.2971(3) 0.055(3) Uani 1 d . . . H21B H 0.2959 -0.1079 0.2820 0.066 Uiso 1 calc R . . C22B C 0.0216(17) -0.1234(4) 0.2915(3) 0.051(3) Uani 1 d . . . C23B C -0.0977(18) -0.1556(5) 0.3169(4) 0.068(3) Uani 1 d . . . H23B H -0.2265 -0.1487 0.3149 0.082 Uiso 1 calc R . . C24B C -0.0336(15) -0.1977(5) 0.3451(3) 0.059(3) Uani 1 d . . . H24B H -0.1182 -0.2195 0.3613 0.070 Uiso 1 calc R . . O25B O -0.0511(11) -0.0835(3) 0.2636(2) 0.067(2) Uani 1 d . . . H25B H 0.0346 -0.0644 0.2526 0.101 Uiso 1 calc R . . O30 O -0.1005(14) -0.4773(4) -1.0332(2) 0.077(2) Uani 1 d . . . H30 H -0.1243 -0.5140 -1.0331 0.116 Uiso 1 calc R . . O31 O -0.0810(12) -0.3900(4) -0.8013(2) 0.071(2) Uani 1 d . . . H31A H -0.1411 -0.4124 -0.7858 0.107 Uiso 1 calc R . . C30 C -0.0930(18) -0.4559(6) -0.9930(3) 0.066(3) Uani 1 d . . . C31 C -0.1058(18) -0.3919(5) -0.9885(4) 0.070(3) Uani 1 d . . . H31 H -0.1198 -0.3674 -1.0118 0.084 Uiso 1 calc R . . C32 C -0.0977(19) -0.3654(5) -0.9500(4) 0.072(3) Uani 1 d . . . H32 H -0.1008 -0.3231 -0.9472 0.086 Uiso 1 calc R . . C33 C -0.0845(14) -0.4040(5) -0.9143(3) 0.052(3) Uani 1 d . . . C34 C -0.0754(13) -0.4674(4) -0.9197(3) 0.046(2) Uani 1 d . . . C35 C -0.0778(15) -0.4931(5) -0.9600(3) 0.052(3) Uani 1 d . . . H35 H -0.0690 -0.5352 -0.9636 0.062 Uiso 1 calc R . . C36 C -0.0645(16) -0.4790(5) -0.8456(3) 0.062(3) Uani 1 d . . . H36 H -0.0549 -0.5039 -0.8224 0.074 Uiso 1 calc R . . C37 C -0.0776(15) -0.4152(5) -0.8410(3) 0.054(3) Uani 1 d . . . C38 C -0.0850(15) -0.3787(5) -0.8745(3) 0.053(3) Uani 1 d . . . H38 H -0.0905 -0.3365 -0.8711 0.063 Uiso 1 calc R . . C39 C -0.0659(17) -0.5045(5) -0.8846(3) 0.063(3) Uani 1 d . . . H39 H -0.0604 -0.5467 -0.8876 0.076 Uiso 1 calc R . . O40 O -0.1142(11) -0.2669(3) -0.7717(2) 0.073(2) Uani 1 d . . . O50 O -0.8679(12) -0.0981(3) -0.4561(2) 0.072(2) Uani 1 d . . . O60 O 0.0884(11) -0.1639(3) -0.5312(2) 0.0598(19) Uani 1 d . . . O70 O -0.5008(18) -0.0088(4) -0.3419(3) 0.127(4) Uani 1 d . . . O80 O 0.3348(11) -0.0147(4) -0.2589(2) 0.070(2) Uani 1 d . . . O90 O -0.6099(15) -0.2863(6) -0.9652(3) 0.136(5) Uani 1 d . . . O100 O -0.129(2) -0.4731(6) -0.1177(3) 0.158(6) Uani 1 d . . . O110 O -0.557(2) -0.1588(5) -0.3008(4) 0.157(6) Uani 1 d . . . O120 O -0.857(3) -0.1023(9) -0.3444(4) 0.232(9) Uani 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 S1A 0.0497(15) 0.0674(15) 0.0450(12) 0.0108(11) -0.0112(13) -0.0004(15) C2A 0.044(6) 0.069(7) 0.038(5) -0.004(5) -0.002(5) -0.007(5) C3A 0.027(5) 0.059(6) 0.052(5) -0.004(5) -0.009(4) 0.001(5) C4A 0.043(6) 0.045(5) 0.050(5) -0.001(4) -0.009(5) 0.000(5) N5A 0.038(4) 0.039(4) 0.038(4) 0.002(3) -0.007(4) 0.004(4) C6A 0.038(5) 0.052(6) 0.043(5) 0.015(4) -0.010(4) -0.012(5) C7A 0.038(6) 0.046(5) 0.049(5) 0.007(4) -0.002(5) 0.001(5) C8A 0.045(6) 0.048(5) 0.037(5) 0.001(4) -0.005(5) -0.003(5) C9A 0.069(8) 0.048(6) 0.047(6) 0.002(5) -0.006(6) 0.005(6) C10A 0.070(8) 0.058(6) 0.062(6) -0.018(5) 0.001(6) -0.015(6) O11A 0.066(5) 0.058(4) 0.069(5) 0.018(4) -0.017(4) -0.012(4) O12A 0.108(8) 0.079(5) 0.069(5) 0.025(4) -0.043(5) -0.026(5) O13A 0.081(5) 0.067(4) 0.033(3) -0.002(3) 0.005(4) 0.011(5) N14A 0.038(5) 0.039(4) 0.070(5) 0.016(4) -0.005(4) -0.004(4) C15A 0.041(6) 0.051(6) 0.038(4) 0.008(4) 0.002(5) 0.001(5) O16A 0.045(5) 0.068(5) 0.089(6) 0.026(4) 0.010(4) -0.001(4) C17A 0.049(6) 0.039(5) 0.043(5) 0.000(4) 0.000(5) 0.010(5) N18A 0.071(7) 0.044(5) 0.063(5) -0.008(4) -0.016(5) 0.013(5) C19A 0.034(5) 0.042(5) 0.045(5) 0.000(4) -0.003(4) 0.013(4) C20A 0.050(6) 0.065(7) 0.041(5) -0.016(5) 0.002(5) 0.005(6) C21A 0.043(6) 0.060(6) 0.060(6) -0.012(5) 0.009(5) 0.015(5) C22A 0.041(6) 0.046(6) 0.072(7) -0.008(5) -0.004(6) 0.000(5) C23A 0.039(6) 0.078(8) 0.085(8) -0.013(7) 0.003(6) -0.013(6) C24A 0.041(6) 0.078(8) 0.068(7) -0.003(6) 0.009(6) -0.007(6) O25A 0.071(6) 0.069(5) 0.088(5) -0.016(4) -0.032(5) -0.005(5) S1B 0.0569(17) 0.0785(18) 0.0446(12) 0.0183(12) -0.0101(14) -0.0045(17) C2B 0.038(6) 0.054(6) 0.065(6) 0.021(5) -0.008(5) -0.003(5) C3B 0.045(6) 0.052(6) 0.057(6) 0.002(5) 0.000(5) 0.001(5) C4B 0.036(5) 0.045(5) 0.042(5) 0.001(4) -0.007(4) -0.008(5) N5B 0.047(5) 0.041(4) 0.032(4) 0.000(3) 0.001(4) 0.001(4) C6B 0.027(5) 0.081(7) 0.032(5) 0.004(5) -0.001(4) 0.005(5) C7B 0.036(5) 0.057(6) 0.051(5) -0.017(5) -0.010(5) 0.002(5) C8B 0.058(7) 0.048(5) 0.031(4) 0.004(4) -0.013(5) -0.002(5) C9B 0.058(7) 0.043(5) 0.040(5) -0.007(5) -0.003(5) -0.001(5) C10B 0.078(9) 0.046(6) 0.096(9) 0.003(6) -0.002(8) -0.011(7) O11B 0.069(5) 0.102(6) 0.049(4) -0.004(4) 0.012(4) 0.004(5) O12B 0.057(5) 0.078(5) 0.047(4) 0.014(4) -0.001(4) 0.001(4) O13B 0.076(5) 0.049(4) 0.048(4) 0.000(3) -0.008(4) -0.006(4) N14B 0.031(4) 0.064(5) 0.056(5) -0.025(4) -0.002(4) 0.014(4) C15B 0.041(6) 0.046(5) 0.035(4) -0.007(4) 0.005(4) 0.005(5) O16B 0.044(4) 0.093(5) 0.049(4) -0.024(4) 0.002(3) 0.022(4) C17B 0.041(6) 0.043(5) 0.039(5) -0.003(4) 0.007(4) 0.004(5) N18B 0.059(5) 0.045(4) 0.035(4) 0.002(3) -0.003(4) -0.006(4) C19B 0.037(5) 0.042(5) 0.040(5) -0.005(4) -0.003(4) -0.008(5) C20B 0.044(6) 0.047(6) 0.063(6) 0.008(5) -0.004(5) -0.003(5) C21B 0.058(7) 0.053(6) 0.054(6) 0.004(5) 0.006(6) -0.004(6) C22B 0.060(7) 0.043(5) 0.050(5) -0.002(4) -0.004(6) -0.015(6) C23B 0.047(7) 0.057(7) 0.100(9) 0.018(7) -0.023(7) -0.001(6) C24B 0.036(6) 0.073(7) 0.067(7) 0.021(6) 0.003(5) 0.008(6) O25B 0.064(5) 0.066(5) 0.071(5) 0.018(4) -0.029(4) -0.008(4) O30 0.087(7) 0.085(5) 0.060(5) 0.001(4) -0.003(5) 0.004(6) O31 0.065(6) 0.088(6) 0.061(4) -0.012(4) 0.000(4) -0.011(5) C30 0.055(8) 0.084(8) 0.060(7) 0.001(6) 0.004(6) -0.005(7) C31 0.067(9) 0.065(7) 0.078(8) 0.021(6) 0.002(7) 0.001(7) C32 0.067(9) 0.061(7) 0.087(8) 0.005(6) 0.000(8) -0.005(7) C33 0.032(5) 0.059(6) 0.064(6) 0.013(5) 0.006(5) -0.003(5) C34 0.025(5) 0.049(6) 0.064(6) 0.010(5) -0.005(5) 0.009(5) C35 0.044(6) 0.055(6) 0.056(6) -0.003(5) -0.002(5) 0.008(5) C36 0.058(7) 0.071(7) 0.056(6) 0.000(6) -0.003(6) 0.006(6) C37 0.036(6) 0.067(7) 0.060(6) -0.002(6) -0.004(5) -0.007(5) C38 0.038(6) 0.046(6) 0.075(7) -0.002(5) -0.007(6) -0.002(5) C39 0.061(8) 0.063(7) 0.065(6) 0.007(5) -0.001(6) 0.006(6) O40 0.050(5) 0.076(5) 0.093(5) 0.007(4) 0.004(4) 0.021(4) O50 0.072(6) 0.080(5) 0.063(4) 0.000(4) 0.010(4) 0.003(5) O60 0.049(4) 0.056(4) 0.074(5) 0.003(4) 0.012(4) 0.008(4) O70 0.166(11) 0.131(8) 0.084(6) -0.043(5) 0.018(7) -0.090(9) O80 0.065(5) 0.077(5) 0.067(5) -0.020(4) 0.002(4) 0.004(5) O90 0.073(7) 0.242(13) 0.093(6) -0.066(8) -0.014(6) 0.040(9) O100 0.176(13) 0.219(13) 0.079(6) 0.051(8) 0.000(8) -0.099(12) O110 0.204(15) 0.108(7) 0.158(10) 0.013(7) 0.123(11) 0.015(9) O120 0.234(19) 0.34(2) 0.118(9) 0.004(12) -0.011(11) -0.172(19) _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 S1A C2A 1.806(10) . Y S1A C6A 1.809(9) . Y C2A C3A 1.526(13) . Y C3A C4A 1.332(12) . Y C3A C10A 1.520(13) . Y C4A N5A 1.417(11) . Y C4A C9A 1.520(13) . Y N5A C8A 1.332(11) . Y N5A C6A 1.451(10) . Y C6A C7A 1.552(13) . Y C7A N14A 1.414(12) . Y C7A C8A 1.542(12) . Y C8A O13A 1.214(10) . Y C9A O12A 1.229(12) . Y C9A O11A 1.269(12) . Y N14A C15A 1.308(11) . Y C15A O16A 1.225(12) . Y C15A C17A 1.519(13) . Y C17A N18A 1.477(12) . Y C17A C19A 1.537(13) . Y C19A C24A 1.364(14) . Y C19A C20A 1.402(13) . Y C20A C21A 1.393(14) . Y C21A C22A 1.396(14) . Y C22A C23A 1.361(15) . Y C22A O25A 1.371(12) . Y C23A C24A 1.370(15) . Y S1B C6B 1.809(10) . Y S1B C2B 1.822(10) . Y C2B C3B 1.521(13) . Y C3B C4B 1.318(12) . Y C3B C10B 1.545(14) . Y C4B N5B 1.409(11) . Y C4B C9B 1.512(12) . Y N5B C8B 1.348(11) . Y N5B C6B 1.460(10) . Y C6B C7B 1.532(13) . Y C7B N14B 1.421(12) . Y C7B C8B 1.518(12) . Y C8B O13B 1.212(10) . Y C9B O12B 1.229(12) . Y C9B O11B 1.239(13) . Y N14B C15B 1.360(10) . Y C15B O16B 1.211(11) . Y C15B C17B 1.551(14) . Y C17B N18B 1.495(11) . Y C17B C19B 1.521(13) . Y C19B C24B 1.362(14) . Y C19B C20B 1.387(13) . Y C20B C21B 1.384(14) . Y C21B C22B 1.375(16) . Y C22B O25B 1.358(11) . Y C22B C23B 1.373(15) . Y C23B C24B 1.372(13) . Y O30 C30 1.383(13) . Y O31 C37 1.398(11) . Y C30 C35 1.344(14) . Y C30 C31 1.409(15) . Y C31 C32 1.372(15) . Y C32 C33 1.432(14) . Y C33 C34 1.400(13) . Y C33 C38 1.402(14) . Y C34 C39 1.393(13) . Y C34 C35 1.420(13) . Y C36 C39 1.378(14) . Y C36 C37 1.404(14) . Y C37 C38 1.344(13) . Y 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 C2A S1A C6A 95.4(4) . . Y C3A C2A S1A 116.3(7) . . Y C4A C3A C10A 123.4(9) . . Y C4A C3A C2A 124.6(9) . . Y C10A C3A C2A 111.9(8) . . Y C3A C4A N5A 119.2(8) . . Y C3A C4A C9A 125.9(9) . . Y N5A C4A C9A 114.7(8) . . Y C8A N5A C4A 133.8(8) . . Y C8A N5A C6A 95.7(7) . . Y C4A N5A C6A 126.6(7) . . Y N5A C6A C7A 87.8(6) . . Y N5A C6A S1A 109.7(6) . . Y C7A C6A S1A 115.5(7) . . Y N14A C7A C8A 115.7(8) . . Y N14A C7A C6A 119.8(8) . . Y C8A C7A C6A 83.7(6) . . Y O13A C8A N5A 133.8(9) . . Y O13A C8A C7A 133.5(9) . . Y N5A C8A C7A 92.6(7) . . Y O12A C9A O11A 126.2(9) . . Y O12A C9A C4A 117.5(10) . . Y O11A C9A C4A 116.3(9) . . Y C15A N14A C7A 122.8(9) . . Y O16A C15A N14A 124.6(10) . . Y O16A C15A C17A 119.7(8) . . Y N14A C15A C17A 115.6(9) . . Y N18A C17A C15A 110.6(8) . . Y N18A C17A C19A 109.2(7) . . Y C15A C17A C19A 113.3(8) . . Y C24A C19A C20A 119.5(10) . . Y C24A C19A C17A 121.1(9) . . Y C20A C19A C17A 119.2(9) . . Y C21A C20A C19A 119.0(10) . . Y C20A C21A C22A 119.9(10) . . Y C23A C22A O25A 119.9(10) . . Y C23A C22A C21A 119.6(10) . . Y O25A C22A C21A 120.5(10) . . Y C22A C23A C24A 120.7(10) . . Y C19A C24A C23A 121.2(11) . . Y C6B S1B C2B 95.9(4) . . Y C3B C2B S1B 114.9(7) . . Y C4B C3B C2B 124.6(9) . . Y C4B C3B C10B 122.9(9) . . Y C2B C3B C10B 112.4(8) . . Y C3B C4B N5B 120.5(8) . . Y C3B C4B C9B 125.8(9) . . Y N5B C4B C9B 113.7(7) . . Y C8B N5B C4B 133.9(8) . . Y C8B N5B C6B 94.1(7) . . Y C4B N5B C6B 126.9(7) . . Y N5B C6B C7B 87.9(7) . . Y N5B C6B S1B 109.5(6) . . Y C7B C6B S1B 118.1(7) . . Y N14B C7B C8B 114.6(9) . . Y N14B C7B C6B 117.2(8) . . Y C8B C7B C6B 84.8(7) . . Y O13B C8B N5B 132.4(8) . . Y O13B C8B C7B 134.8(9) . . Y N5B C8B C7B 92.8(7) . . Y O12B C9B O11B 125.8(9) . . Y O12B C9B C4B 117.0(10) . . Y O11B C9B C4B 117.1(10) . . Y C15B N14B C7B 122.3(8) . . Y O16B C15B N14B 123.9(9) . . Y O16B C15B C17B 122.2(7) . . Y N14B C15B C17B 114.0(8) . . Y N18B C17B C19B 110.3(7) . . Y N18B C17B C15B 105.5(7) . . Y C19B C17B C15B 114.2(8) . . Y C24B C19B C20B 119.8(10) . . Y C24B C19B C17B 118.9(9) . . Y C20B C19B C17B 120.9(9) . . Y C21B C20B C19B 119.5(10) . . Y C22B C21B C20B 121.1(10) . . Y O25B C22B C23B 119.5(11) . . Y O25B C22B C21B 123.0(10) . . Y C23B C22B C21B 117.5(10) . . Y C24B C23B C22B 122.3(11) . . Y C19B C24B C23B 119.5(11) . . Y C35 C30 O30 122.8(10) . . Y C35 C30 C31 121.7(11) . . Y O30 C30 C31 115.5(10) . . Y C32 C31 C30 120.6(11) . . Y C31 C32 C33 118.9(10) . . Y C34 C33 C38 120.3(9) . . Y C34 C33 C32 119.2(10) . . Y C38 C33 C32 120.5(10) . . Y C39 C34 C33 118.6(10) . . Y C39 C34 C35 121.2(9) . . Y C33 C34 C35 120.3(9) . . Y C30 C35 C34 119.3(10) . . Y C39 C36 C37 119.8(10) . . Y C38 C37 O31 120.2(10) . . Y C38 C37 C36 120.6(10) . . Y O31 C37 C36 119.3(9) . . Y C37 C38 C33 120.2(9) . . Y C36 C39 C34 120.5(10) . . Y _diffrn_reflns_theta_full 70.05 _refine_diff_density_max 0.452 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.091 _publ_section_experimental ; Crystal colour: transparent colourless, crystal shape: rather regular needle. Profile analysis combining the methods of Lehman & Larsen (1974) and Grant & Gabe (1978). Empirical absorption correction using EMPABS (North, Phillips & Mathews, 1968). Data collection parameters: \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.50 + 0.19tan\q)\%, range: 0.77\%-1.55\%, aperture (1.52 + 0.16tan\q)mm., range: 1.53-1.95mm. Maximum scan time: 30 sec/reflection. Least-squares refinement using calculated weights: w=1/[\s^2^(Fo^2^)+(0.1207P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; #===END