# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_global # *** Added by check_cif _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Amiens, C.' 'Chaudret, Bruno' 'Coppel, Yannick' 'Donnadieu, Bruno' 'Uznanski, P.' _publ_contact_author_name 'Dr P Uznanski' _publ_contact_author_address ; Centre for Molecular & Macromolecular Studies, PAS Sienkiewicza 112 Lodz 90-363 POLAND ; _publ_contact_author_email 'PUZNANSK@BILBO.CBMM.LODZ.PL' _publ_section_title ; Oxidation of photochromic spirooxazines by coinage metal cations. Part I. Reaction with AgNO3: form ation and characterisation of silver particles ; #*********************************************************************** data_1 _database_code_CSD 171832 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23H22N2O2' _chemical_formula_weight 358.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.6277(16) _cell_length_b 8.2069(7) _cell_length_c 15.1464(16) _cell_angle_alpha 90.00 _cell_angle_beta 116.113(11) _cell_angle_gamma 90.00 _cell_volume 1855.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5000 _cell_measurement_2theta_min 4.9 _cell_measurement_2theta_max 47.8 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'orange yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type semi-empirical #(DIFABS - N. Walker and D. Stuart, Acta Crystallogr., Sect A 1983, 39, #158-166) _exptl_absorpt_correction_T_min 0.56 _exptl_absorpt_correction_T_max 0.87 _exptl_special_details ; The data was collected at low temperature (T=180K) on a STOE imaging plate diffraction system (I.P.D.S), equipped with an Oxford cryosystems cooler device, the crystal-to-detector distance was 80mm, 167 exposures were obtained with 0<(<250° and with the crystal rotated through 1.5° in (. Coverage of the unique set has been 99.9% complete to at least 24.2°. Crystal decay was monitored by measuring 200 reflections by image. The final unit cell parameters was obtained by the least-squares refinement of 5000 reflections. Any significant fluctuations in the intensity monitors were observed during the data collection. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK( _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Stoe and Cie (1996) IPDS Manual. Version 2.75. Stoe and Cie, Darmstadt, Germany ; #_diffrn_measurement_method 'rotation en (' #_diffrn_detector_area_resol_mean '2( (2.90 -48.4)' #_d(hkl) range (14.228 - 0.8567)Å _diffrn_standards_number 200 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13104 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 26.17 _reflns_number_total 3449 _reflns_number_gt 2574 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Stoe and Cie (1996) IPDS Manual. Version 2.75 Stoe and Cie, Darmstadt, Germany ; _computing_cell_refinement ; Stoe and Cie (1996) IPDS Manual. Version 2.75 Stoe and Cie, Darmstadt, Germany ; _computing_data_reduction ; Stoe and Cie (1996) IPDS Manual. Version 2.75 Stoe and Cie, Darmstadt, Germany ; _computing_structure_solution ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Zsolnai,L.(1997). ZORTEP.Molecular Graphics Program.University of Heidelberg, Germany. ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' #a CIFTAB program _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0533P)^2^+0.3429P] 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_number_reflns 3449 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0932 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.003 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.80146(6) 0.33329(13) 0.55781(7) 0.0297(2) Uani 1 1 d . . . O2 O 0.82368(7) 0.33837(15) 0.33613(8) 0.0410(3) Uani 1 1 d . . . N1 N 0.72107(8) 0.47197(16) 0.37090(8) 0.0317(3) Uani 1 1 d . . . N2 N 0.90293(7) 0.20105(16) 0.51618(9) 0.0319(3) Uani 1 1 d . . . C1 C 0.81101(9) 0.24720(18) 0.47866(9) 0.0272(3) Uani 1 1 d . . . C2 C 0.72935(9) 0.43451(18) 0.53251(10) 0.0286(3) Uani 1 1 d . . . C3 C 0.70352(11) 0.4750(2) 0.60626(11) 0.0367(4) Uani 1 1 d . . . H3 H 0.7348 0.4306 0.6704 0.044 Uiso 1 1 calc R . . C4 C 0.63342(12) 0.5780(2) 0.58540(13) 0.0434(4) Uani 1 1 d . . . H4 H 0.6162 0.6056 0.6356 0.052 Uiso 1 1 calc R . . C5 C 0.58583(10) 0.6446(2) 0.49061(12) 0.0387(4) Uani 1 1 d . . . C6 C 0.51284(11) 0.7527(2) 0.46711(16) 0.0504(5) Uani 1 1 d . . . H6 H 0.4939 0.7801 0.5160 0.060 Uiso 1 1 calc R . . C7 C 0.46956(11) 0.8177(2) 0.37565(16) 0.0544(5) Uani 1 1 d . . . H7 H 0.4207 0.8899 0.3612 0.065 Uiso 1 1 calc R . . C8 C 0.49600(11) 0.7796(2) 0.30281(14) 0.0500(5) Uani 1 1 d . . . H8 H 0.4651 0.8262 0.2392 0.060 Uiso 1 1 calc R . . C9 C 0.56634(10) 0.6754(2) 0.32200(12) 0.0408(4) Uani 1 1 d . . . H9 H 0.5838 0.6504 0.2717 0.049 Uiso 1 1 calc R . . C10 C 0.61287(9) 0.60531(19) 0.41635(11) 0.0334(3) Uani 1 1 d . . . C11 C 0.68697(9) 0.49860(19) 0.43987(10) 0.0299(3) Uani 1 1 d . . . C12 C 0.78058(9) 0.36285(19) 0.39167(10) 0.0305(3) Uani 1 1 d . . . C13 C 0.91424(9) 0.05150(19) 0.56381(10) 0.0296(3) Uani 1 1 d . . . C14 C 0.99265(10) -0.0205(2) 0.63055(11) 0.0399(4) Uani 1 1 d . . . H14 H 1.0489 0.0321 0.6505 0.048 Uiso 1 1 calc R . . C15 C 0.98626(11) -0.1722(2) 0.66731(12) 0.0463(4) Uani 1 1 d . . . H15 H 1.0392 -0.2241 0.7134 0.056 Uiso 1 1 calc R . . C16 C 0.90517(12) -0.2498(2) 0.63885(13) 0.0461(4) Uani 1 1 d . . . H16 H 0.9027 -0.3538 0.6651 0.055 Uiso 1 1 calc R . . C17 C 0.82669(11) -0.1754(2) 0.57149(11) 0.0372(4) Uani 1 1 d . . . H17 H 0.7704 -0.2278 0.5515 0.045 Uiso 1 1 calc R . . C18 C 0.83211(9) -0.02520(18) 0.53448(10) 0.0282(3) Uani 1 1 d . . . C19 C 0.76035(9) 0.07972(18) 0.45813(10) 0.0277(3) Uani 1 1 d . . . C1A C 0.74142(11) 0.0155(2) 0.35604(10) 0.0383(4) Uani 1 1 d . . . H1A1 H 0.6960 0.0841 0.3057 0.057 Uiso 1 1 calc R . . H1A2 H 0.7194 -0.0968 0.3491 0.057 Uiso 1 1 calc R . . H1A3 H 0.7967 0.0181 0.3479 0.057 Uiso 1 1 calc R . . C2A C 0.97258(10) 0.3232(2) 0.55191(13) 0.0454(4) Uani 1 1 d . . . H2A1 H 0.9493 0.4259 0.5170 0.068 Uiso 1 1 calc R . . H2A2 H 1.0234 0.2868 0.5405 0.068 Uiso 1 1 calc R . . H2A3 H 0.9924 0.3396 0.6225 0.068 Uiso 1 1 calc R . . C1B C 0.67290(9) 0.0838(2) 0.46756(11) 0.0336(3) Uani 1 1 d . . . H1B1 H 0.6304 0.1566 0.4174 0.050 Uiso 1 1 calc R . . H1B2 H 0.6844 0.1238 0.5330 0.050 Uiso 1 1 calc R . . H1B3 H 0.6476 -0.0262 0.4583 0.050 Uiso 1 1 calc R . . C2B C 0.80410(12) 0.4526(3) 0.25720(12) 0.0479(5) Uani 1 1 d . . . H2B1 H 0.8402 0.4263 0.2225 0.072 Uiso 1 1 calc R . . H2B2 H 0.8184 0.5632 0.2841 0.072 Uiso 1 1 calc R . . H2B3 H 0.7404 0.4462 0.2113 0.072 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0333(5) 0.0307(6) 0.0249(5) 0.0010(4) 0.0128(4) 0.0011(4) O2 0.0483(6) 0.0488(8) 0.0368(6) 0.0145(5) 0.0286(5) 0.0098(5) N1 0.0338(6) 0.0326(8) 0.0273(6) 0.0024(5) 0.0122(5) 0.0001(5) N2 0.0244(6) 0.0361(8) 0.0355(6) 0.0070(5) 0.0135(5) -0.0007(5) C1 0.0274(7) 0.0305(9) 0.0256(7) 0.0017(6) 0.0135(6) 0.0003(6) C2 0.0307(7) 0.0250(9) 0.0319(7) -0.0011(6) 0.0153(6) -0.0031(6) C3 0.0471(9) 0.0345(10) 0.0358(8) 0.0012(6) 0.0249(7) -0.0016(7) C4 0.0541(10) 0.0376(11) 0.0528(10) -0.0019(7) 0.0365(8) -0.0012(8) C5 0.0346(8) 0.0309(10) 0.0561(10) -0.0027(7) 0.0250(7) -0.0041(6) C6 0.0414(9) 0.0415(12) 0.0785(13) -0.0027(9) 0.0358(9) -0.0009(8) C7 0.0319(8) 0.0413(12) 0.0842(14) 0.0012(10) 0.0202(9) 0.0027(7) C8 0.0355(8) 0.0353(11) 0.0589(11) 0.0004(8) 0.0023(8) -0.0010(7) C9 0.0360(8) 0.0310(10) 0.0432(9) -0.0022(7) 0.0063(7) -0.0025(7) C10 0.0294(7) 0.0264(9) 0.0409(8) -0.0031(6) 0.0121(6) -0.0049(6) C11 0.0309(7) 0.0274(9) 0.0318(7) -0.0021(6) 0.0140(6) -0.0031(6) C12 0.0333(7) 0.0329(9) 0.0284(7) 0.0036(6) 0.0164(6) -0.0004(6) C13 0.0310(7) 0.0338(9) 0.0273(7) 0.0013(6) 0.0157(6) 0.0042(6) C14 0.0307(8) 0.0495(11) 0.0379(8) 0.0033(7) 0.0135(7) 0.0081(7) C15 0.0460(9) 0.0484(12) 0.0407(9) 0.0097(8) 0.0157(8) 0.0198(8) C16 0.0613(11) 0.0298(10) 0.0435(9) 0.0076(7) 0.0196(8) 0.0102(8) C17 0.0445(9) 0.0291(10) 0.0353(8) -0.0012(6) 0.0150(7) -0.0014(7) C18 0.0324(7) 0.0273(9) 0.0251(7) -0.0014(5) 0.0128(6) 0.0014(6) C19 0.0282(7) 0.0299(9) 0.0244(7) 0.0000(6) 0.0111(5) -0.0012(6) C1A 0.0401(8) 0.0449(11) 0.0270(7) -0.0040(7) 0.0121(6) -0.0010(7) C2A 0.0325(8) 0.0484(12) 0.0544(10) 0.0092(8) 0.0183(7) -0.0093(7) C1B 0.0291(7) 0.0350(10) 0.0363(8) 0.0011(6) 0.0141(6) -0.0038(6) C2B 0.0533(10) 0.0607(13) 0.0378(8) 0.0199(8) 0.0273(8) 0.0078(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.3674(17) . ? O1 C1 1.4595(16) . ? O2 C12 1.3388(17) . ? O2 C2B 1.4388(19) . ? N1 C12 1.267(2) . ? N1 C11 1.4078(18) . ? N2 C13 1.3935(19) . ? N2 C1 1.4275(17) . ? N2 C2A 1.445(2) . ? C1 C12 1.5182(19) . ? C1 C19 1.570(2) . ? C2 C11 1.368(2) . ? C2 C3 1.402(2) . ? C3 C4 1.360(2) . ? C3 H3 0.9500 . ? C4 C5 1.409(2) . ? C4 H4 0.9500 . ? C5 C6 1.416(2) . ? C5 C10 1.420(2) . ? C6 C7 1.358(3) . ? C6 H6 0.9500 . ? C7 C8 1.391(3) . ? C7 H7 0.9500 . ? C8 C9 1.373(2) . ? C8 H8 0.9500 . ? C9 C10 1.414(2) . ? C9 H9 0.9500 . ? C10 C11 1.423(2) . ? C13 C14 1.382(2) . ? C13 C18 1.387(2) . ? C14 C15 1.387(3) . ? C14 H14 0.9500 . ? C15 C16 1.377(3) . ? C15 H15 0.9500 . ? C16 C17 1.394(2) . ? C16 H16 0.9500 . ? C17 C18 1.373(2) . ? C17 H17 0.9500 . ? C18 C19 1.5122(19) . ? C19 C1B 1.5228(19) . ? C19 C1A 1.5297(19) . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? C2A H2A1 0.9800 . ? C2A H2A2 0.9800 . ? C2A H2A3 0.9800 . ? C1B H1B1 0.9800 . ? C1B H1B2 0.9800 . ? C1B H1B3 0.9800 . ? C2B H2B1 0.9800 . ? C2B H2B2 0.9800 . ? C2B H2B3 0.9800 . ? 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 C2 O1 C1 117.58(10) . . ? C12 O2 C2B 115.85(12) . . ? C12 N1 C11 116.83(12) . . ? C13 N2 C1 108.44(11) . . ? C13 N2 C2A 120.92(12) . . ? C1 N2 C2A 120.42(14) . . ? N2 C1 O1 106.62(10) . . ? N2 C1 C12 113.61(11) . . ? O1 C1 C12 107.16(12) . . ? N2 C1 C19 103.52(12) . . ? O1 C1 C19 110.13(10) . . ? C12 C1 C19 115.48(11) . . ? O1 C2 C11 120.87(12) . . ? O1 C2 C3 117.33(13) . . ? C11 C2 C3 121.74(14) . . ? C4 C3 C2 119.63(15) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 121.14(15) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 122.23(16) . . ? C4 C5 C10 119.17(15) . . ? C6 C5 C10 118.59(16) . . ? C7 C6 C5 120.85(18) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 120.69(17) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C9 C8 C7 120.63(18) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 120.23(17) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C5 119.02(15) . . ? C9 C10 C11 122.11(14) . . ? C5 C10 C11 118.87(14) . . ? C2 C11 N1 120.50(13) . . ? C2 C11 C10 119.43(13) . . ? N1 C11 C10 119.81(13) . . ? N1 C12 O2 121.72(13) . . ? N1 C12 C1 125.61(12) . . ? O2 C12 C1 112.66(12) . . ? C14 C13 C18 121.28(15) . . ? C14 C13 N2 128.57(14) . . ? C18 C13 N2 110.14(12) . . ? C13 C14 C15 117.56(15) . . ? C13 C14 H14 121.2 . . ? C15 C14 H14 121.2 . . ? C16 C15 C14 121.78(15) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C15 C16 C17 119.94(17) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C18 C17 C16 118.86(15) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C17 C18 C13 120.59(14) . . ? C17 C18 C19 130.65(13) . . ? C13 C18 C19 108.71(13) . . ? C18 C19 C1B 113.92(12) . . ? C18 C19 C1A 108.59(12) . . ? C1B C19 C1A 108.81(12) . . ? C18 C19 C1 99.95(11) . . ? C1B C19 C1 114.40(12) . . ? C1A C19 C1 110.86(12) . . ? C19 C1A H1A1 109.5 . . ? C19 C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? C19 C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? N2 C2A H2A1 109.5 . . ? N2 C2A H2A2 109.5 . . ? H2A1 C2A H2A2 109.5 . . ? N2 C2A H2A3 109.5 . . ? H2A1 C2A H2A3 109.5 . . ? H2A2 C2A H2A3 109.5 . . ? C19 C1B H1B1 109.5 . . ? C19 C1B H1B2 109.5 . . ? H1B1 C1B H1B2 109.5 . . ? C19 C1B H1B3 109.5 . . ? H1B1 C1B H1B3 109.5 . . ? H1B2 C1B H1B3 109.5 . . ? O2 C2B H2B1 109.5 . . ? O2 C2B H2B2 109.5 . . ? H2B1 C2B H2B2 109.5 . . ? O2 C2B H2B3 109.5 . . ? H2B1 C2B H2B3 109.5 . . ? H2B2 C2B H2B3 109.5 . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 26.17 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 0.176 _refine_diff_density_min -0.125 _refine_diff_density_rms 0.033 #*********************************************************************** data_2 _database_code_CSD 171833 _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23H22N2O2' _chemical_formula_weight 358.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.659(3) _cell_length_b 8.4635(11) _cell_length_c 16.5591(17) _cell_angle_alpha 90.00 _cell_angle_beta 100.371(12) _cell_angle_gamma 90.00 _cell_volume 3813.1(7) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5000 _cell_measurement_2theta_min 4.9 _cell_measurement_2theta_max 47.8 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'orange yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type semi-empirical #(DIFABS - N. Walker and D. Stuart, Acta Crystallogr., Sect A 1983, 39, #158-166) _exptl_absorpt_correction_T_min 0.51 _exptl_absorpt_correction_T_max 0.85 _exptl_special_details ; The data was collected at low temperature (T=298K) on a STOE imaging plate diffraction system (I.P.D.S), equipped with an Oxford cryosystems cooler device, the crystal-to-detector distance was 80mm, 147 exposures were obtained with 0<(<250° and with the crystal rotated through 1.7° in (. Coverage of the unique set has been 99.9% complete to at least 24.2°. Crystal decay was monitored by measuring 200 reflections by image. The final unit cell parameters was obtained by the least-squares refinement of 5000 reflections. Any significant fluctuations in the intensity monitors were observed during the data collection. ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\( _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Stoe and Cie (1996) IPDS Manual. Version 2.75. Stoe and Cie, Darmstadt, Germany ; #_diffrn_measurement_method 'rotation en (' #_diffrn_detector_area_resol_mean '2( (2.90 -48.4)' #_d(hkl) range (14.228 - 0.8567) _diffrn_standards_number 200 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13382 _diffrn_reflns_av_R_equivalents 0.0801 _diffrn_reflns_av_sigmaI/netI 0.0658 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 23.26 _reflns_number_total 2744 _reflns_number_gt 1320 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Stoe and Cie (1996) IPDS Manual. Version 2.75 Stoe and Cie, Darmstadt, Germany ; _computing_cell_refinement ; Stoe and Cie (1996) IPDS Manual. Version 2.75 Stoe and Cie, Darmstadt, Germany ; _computing_data_reduction ; Stoe and Cie (1996) IPDS Manual. Version 2.75 Stoe and Cie, Darmstadt, Germany ; _computing_structure_solution ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Zsolnai,L.(1997). ZORTEP.Molecular Graphics Program.University of Heidelberg, Germany. ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' #a CIFTAB program _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0768P)^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_number_reflns 2744 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1192 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1527 _refine_ls_wR_factor_gt 0.1156 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.940 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.36086(9) 0.2277(3) 0.53408(15) 0.0638(7) Uani 1 1 d . . . O2 O 0.47541(9) 0.2433(3) 0.46698(17) 0.0741(8) Uani 1 1 d . . . N1 N 0.43177(11) 0.3634(4) 0.58824(17) 0.0624(9) Uani 1 1 d . . . N2 N 0.40735(11) 0.1004(4) 0.41233(18) 0.0599(8) Uani 1 1 d . . . C1 C 0.40198(13) 0.3158(4) 0.5116(2) 0.0557(9) Uani 1 1 d . . . C2 C 0.42730(13) 0.2091(4) 0.4603(2) 0.0566(9) Uani 1 1 d . . . C3 C 0.35771(13) 0.0657(4) 0.4156(2) 0.0544(9) Uani 1 1 d . . . C4 C 0.33098(14) -0.0386(4) 0.3566(2) 0.0593(10) Uani 1 1 d . . . C5 C 0.35101(16) -0.0991(5) 0.2909(2) 0.0693(11) Uani 1 1 d . . . H5 H 0.3831 -0.0743 0.2860 0.083 Uiso 1 1 calc R . . C6 C 0.3228(2) -0.1960(5) 0.2333(3) 0.0858(14) Uani 1 1 d . . . H6 H 0.3358 -0.2350 0.1893 0.103 Uiso 1 1 calc R . . C7 C 0.2751(2) -0.2346(6) 0.2415(3) 0.0918(15) Uani 1 1 d . . . H7 H 0.2564 -0.2991 0.2024 0.110 Uiso 1 1 calc R . . C8 C 0.25542(17) -0.1808(5) 0.3047(3) 0.0836(14) Uani 1 1 d . . . H8 H 0.2234 -0.2092 0.3087 0.100 Uiso 1 1 calc R . . C9 C 0.28258(14) -0.0815(5) 0.3653(3) 0.0665(11) Uani 1 1 d . . . C10 C 0.26332(15) -0.0234(5) 0.4322(3) 0.0743(12) Uani 1 1 d . . . H10 H 0.2320 -0.0544 0.4388 0.089 Uiso 1 1 calc R . . C11 C 0.28945(14) 0.0776(5) 0.4879(3) 0.0682(11) Uani 1 1 d . . . H11 H 0.2763 0.1152 0.5321 0.082 Uiso 1 1 calc R . . C12 C 0.33632(13) 0.1230(4) 0.4770(2) 0.0579(10) Uani 1 1 d . . . C13 C 0.41340(13) 0.5053(5) 0.6126(2) 0.0605(10) Uani 1 1 d . . . C14 C 0.42178(16) 0.5753(5) 0.6891(2) 0.0760(12) Uani 1 1 d . . . H14 H 0.4416 0.5273 0.7337 0.091 Uiso 1 1 calc R . . C15 C 0.39952(17) 0.7202(5) 0.6970(3) 0.0793(13) Uani 1 1 d . . . H15 H 0.4046 0.7694 0.7480 0.095 Uiso 1 1 calc R . . C16 C 0.37057(16) 0.7923(5) 0.6325(3) 0.0767(12) Uani 1 1 d . . . H16 H 0.3562 0.8893 0.6398 0.092 Uiso 1 1 calc R . . C17 C 0.36243(14) 0.7216(4) 0.5556(2) 0.0661(11) Uani 1 1 d . . . H17 H 0.3428 0.7708 0.5112 0.079 Uiso 1 1 calc R . . C18 C 0.38372(13) 0.5780(4) 0.5461(2) 0.0580(10) Uani 1 1 d . . . C19 C 0.38380(13) 0.4776(4) 0.4705(2) 0.0551(9) Uani 1 1 d . . . C20 C 0.33395(14) 0.4677(5) 0.4132(2) 0.0737(12) Uani 1 1 d . . . H20A H 0.3363 0.3969 0.3687 0.111 Uiso 1 1 calc R . . H20B H 0.3246 0.5707 0.3916 0.111 Uiso 1 1 calc R . . H20C H 0.3097 0.4292 0.4431 0.111 Uiso 1 1 calc R . . C21 C 0.42181(15) 0.5453(5) 0.4227(3) 0.0744(12) Uani 1 1 d . . . H21A H 0.4244 0.4771 0.3773 0.112 Uiso 1 1 calc R . . H21B H 0.4532 0.5523 0.4583 0.112 Uiso 1 1 calc R . . H21C H 0.4116 0.6486 0.4026 0.112 Uiso 1 1 calc R . . C22 C 0.50233(16) 0.1542(6) 0.4156(3) 0.0892(14) Uani 1 1 d . . . H22A H 0.5366 0.1812 0.4289 0.134 Uiso 1 1 calc R . . H22B H 0.4901 0.1787 0.3590 0.134 Uiso 1 1 calc R . . H22C H 0.4983 0.0433 0.4247 0.134 Uiso 1 1 calc R . . C23 C 0.45325(18) 0.2444(5) 0.6474(3) 0.0898(15) Uani 1 1 d . . . H23A H 0.4521 0.1433 0.6208 0.135 Uiso 1 1 calc R . . H23B H 0.4350 0.2398 0.6915 0.135 Uiso 1 1 calc R . . H23C H 0.4868 0.2716 0.6688 0.135 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0693(17) 0.0636(16) 0.0609(15) -0.0050(13) 0.0187(13) -0.0032(13) O2 0.0576(17) 0.0771(19) 0.0889(18) -0.0195(16) 0.0163(14) -0.0012(13) N1 0.072(2) 0.060(2) 0.0498(17) -0.0069(15) -0.0024(16) 0.0086(16) N2 0.062(2) 0.0586(19) 0.0605(18) -0.0053(16) 0.0145(15) -0.0023(16) C1 0.057(2) 0.056(2) 0.053(2) -0.0031(18) 0.0095(18) -0.0009(18) C2 0.053(2) 0.056(2) 0.062(2) -0.002(2) 0.0130(18) 0.0048(18) C3 0.061(2) 0.050(2) 0.053(2) -0.0005(18) 0.0118(18) 0.0016(18) C4 0.073(3) 0.050(2) 0.054(2) 0.0028(19) 0.0067(19) 0.0014(19) C5 0.082(3) 0.063(3) 0.064(2) -0.004(2) 0.015(2) -0.004(2) C6 0.111(4) 0.078(3) 0.065(3) -0.014(2) 0.008(3) -0.011(3) C7 0.103(4) 0.078(3) 0.084(3) -0.010(3) -0.011(3) -0.016(3) C8 0.076(3) 0.076(3) 0.091(3) -0.005(3) -0.005(3) -0.014(2) C9 0.062(2) 0.060(2) 0.073(3) 0.007(2) 0.002(2) -0.003(2) C10 0.060(2) 0.071(3) 0.093(3) 0.003(2) 0.016(2) -0.003(2) C11 0.065(2) 0.064(3) 0.078(3) -0.001(2) 0.021(2) 0.002(2) C12 0.059(2) 0.056(2) 0.058(2) -0.0016(19) 0.0081(19) -0.0026(19) C13 0.063(2) 0.061(2) 0.057(2) -0.0074(19) 0.0079(19) 0.0051(19) C14 0.094(3) 0.077(3) 0.054(2) -0.010(2) 0.006(2) 0.006(2) C15 0.098(3) 0.076(3) 0.065(3) -0.021(2) 0.018(2) -0.004(3) C16 0.090(3) 0.067(3) 0.076(3) -0.015(2) 0.024(2) 0.006(2) C17 0.071(3) 0.053(2) 0.074(3) -0.003(2) 0.013(2) 0.0040(19) C18 0.063(2) 0.057(2) 0.054(2) -0.0033(19) 0.0106(18) -0.0009(19) C19 0.060(2) 0.054(2) 0.0499(19) -0.0013(17) 0.0078(17) 0.0037(17) C20 0.073(3) 0.072(3) 0.068(2) -0.001(2) -0.010(2) 0.011(2) C21 0.088(3) 0.071(3) 0.068(2) -0.002(2) 0.026(2) -0.006(2) C22 0.071(3) 0.095(3) 0.108(3) -0.022(3) 0.037(3) 0.005(2) C23 0.110(4) 0.082(3) 0.068(3) 0.001(2) -0.010(3) 0.030(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.382(4) . ? O1 C1 1.463(4) . ? O2 C2 1.347(4) . ? O2 C22 1.440(5) . ? N1 C13 1.392(5) . ? N1 C1 1.441(4) . ? N1 C23 1.455(5) . ? N2 C2 1.274(4) . ? N2 C3 1.415(5) . ? C1 C2 1.497(5) . ? C1 C19 1.571(5) . ? C3 C12 1.355(5) . ? C3 C4 1.421(5) . ? C4 C5 1.404(5) . ? C4 C9 1.419(5) . ? C5 C6 1.386(5) . ? C5 H5 0.9300 . ? C6 C7 1.389(7) . ? C6 H6 0.9300 . ? C7 C8 1.344(7) . ? C7 H7 0.9300 . ? C8 C9 1.417(6) . ? C8 H8 0.9300 . ? C9 C10 1.402(6) . ? C10 C11 1.366(5) . ? C10 H10 0.9300 . ? C11 C12 1.395(5) . ? C11 H11 0.9300 . ? C13 C14 1.380(5) . ? C13 C18 1.392(5) . ? C14 C15 1.389(6) . ? C14 H14 0.9300 . ? C15 C16 1.359(6) . ? C15 H15 0.9300 . ? C16 C17 1.387(5) . ? C16 H16 0.9300 . ? C17 C18 1.372(5) . ? C17 H17 0.9300 . ? C18 C19 1.514(5) . ? C19 C20 1.529(5) . ? C19 C21 1.537(5) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? 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 C12 O1 C1 117.5(3) . . ? C2 O2 C22 116.6(3) . . ? C13 N1 C1 108.4(3) . . ? C13 N1 C23 121.9(3) . . ? C1 N1 C23 119.9(3) . . ? C2 N2 C3 116.1(3) . . ? N1 C1 O1 105.4(3) . . ? N1 C1 C2 114.6(3) . . ? O1 C1 C2 107.6(3) . . ? N1 C1 C19 103.0(3) . . ? O1 C1 C19 110.6(3) . . ? C2 C1 C19 115.2(3) . . ? N2 C2 O2 121.1(3) . . ? N2 C2 C1 126.5(3) . . ? O2 C2 C1 112.3(3) . . ? C12 C3 N2 120.8(3) . . ? C12 C3 C4 119.7(4) . . ? N2 C3 C4 119.4(4) . . ? C5 C4 C9 119.8(4) . . ? C5 C4 C3 122.0(4) . . ? C9 C4 C3 118.2(4) . . ? C6 C5 C4 119.8(4) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 119.9(5) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 121.5(4) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C9 121.0(5) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C10 C9 C8 122.7(4) . . ? C10 C9 C4 119.3(4) . . ? C8 C9 C4 118.0(4) . . ? C11 C10 C9 121.6(4) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C10 C11 C12 118.4(4) . . ? C10 C11 H11 120.8 . . ? C12 C11 H11 120.8 . . ? C3 C12 O1 121.1(3) . . ? C3 C12 C11 122.7(4) . . ? O1 C12 C11 116.2(4) . . ? C14 C13 N1 128.8(4) . . ? C14 C13 C18 120.9(4) . . ? N1 C13 C18 110.3(3) . . ? C13 C14 C15 117.5(4) . . ? C13 C14 H14 121.2 . . ? C15 C14 H14 121.2 . . ? C16 C15 C14 122.1(4) . . ? C16 C15 H15 119.0 . . ? C14 C15 H15 119.0 . . ? C15 C16 C17 120.2(4) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C18 C17 C16 119.0(4) . . ? C18 C17 H17 120.5 . . ? C16 C17 H17 120.5 . . ? C17 C18 C13 120.3(3) . . ? C17 C18 C19 131.1(3) . . ? C13 C18 C19 108.5(3) . . ? C18 C19 C20 114.2(3) . . ? C18 C19 C21 108.7(3) . . ? C20 C19 C21 108.9(3) . . ? C18 C19 C1 100.4(3) . . ? C20 C19 C1 113.8(3) . . ? C21 C19 C1 110.6(3) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O2 C22 H22A 109.5 . . ? O2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N1 C23 H23A 109.5 . . ? N1 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N1 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.138 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.038 #*********************************************************************** data_3 _database_code_CSD 171834 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27H24N2O2' _chemical_formula_weight 408.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.450(3) _cell_length_b 20.456(4) _cell_length_c 7.667(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.61(3) _cell_angle_gamma 90.00 _cell_volume 2095.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5000 _cell_measurement_2theta_min 3.6 _cell_measurement_2theta_max 48.2 _exptl_crystal_description parallelepiped _exptl_crystal_colour yellow _exptl_crystal_size_max 0.370 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type semi-empirical #(DIFABS - N. Walker and D. Stuart, Acta Crystallogr., Sect A 1983, 39, #158-166) _exptl_absorpt_correction_T_min 0.41 _exptl_absorpt_correction_T_max 0.80 _exptl_special_details ; The data was collected at low temperature (T=180K) on a STOE imaging plate diffraction system (I.P.D.S), equipped with an Oxford cryosystems cooler device, the crystal-to-detector distance was 80mm, 167 exposures were obtained with 0<(<200° and with the crystal rotated through 2.0° in (. Coverage of the unique set has been 98.6% complete to at least 24.2°. Crystal decay was monitored by measuring 100 reflections by image. The final unit cell parameters was obtained by the least-squares refinement of 5000 reflections. Any significant fluctuations in the intensity monitors were observed during the data collection. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\( _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Stoe and Cie (1996) IPDS Manual. Version 2.75. Stoe and Cie, Darmstadt, Germany ; #_diffrn_measurement_method rotation en ( #_diffrn_detector_area_resol_mean 2( (2.90 -48.4) #_d(hkl) range (14.228 - 0.8567) _diffrn_standards_number 200 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12417 _diffrn_reflns_av_R_equivalents 0.1076 _diffrn_reflns_av_sigmaI/netI 0.1018 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 23.25 _reflns_number_total 2978 _reflns_number_gt 1487 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Stoe and Cie (1996) IPDS Manual. Version 2.75 Stoe and Cie, Darmstadt, Germany. ; _computing_cell_refinement ; Stoe and Cie (1996) IPDS Manual. Version 2.75 Stoe and Cie, Darmstadt, Germany. ; _computing_data_reduction ; Stoe and Cie (1996) IPDS Manual. Version 2.75 Stoe and Cie, Darmstadt, Germany. ; _computing_structure_solution ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435. ; _computing_structure_refinement ; SHELXL-97 (Sheldrick, 1997) ; _computing_molecular_graphics ; Zsolnai,L.(1997). ZORTEP.Molecular Graphics Program.University of Heidelberg, Germany. ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' #a CIFTAB program _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0990P)^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_number_reflns 2978 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1302 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1799 _refine_ls_wR_factor_gt 0.1441 _refine_ls_goodness_of_fit_ref 0.902 _refine_ls_restrained_S_all 0.902 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3755(3) 0.06963(17) 0.4404(5) 0.0341(10) Uani 1 1 d . . . N2 N 0.1389(3) -0.00934(16) 0.4893(4) 0.0289(9) Uani 1 1 d . . . O1 O 0.1801(2) 0.06046(13) 0.2748(4) 0.0334(8) Uani 1 1 d . . . O2 O 0.3282(2) -0.00254(14) 0.6445(4) 0.0356(8) Uani 1 1 d . . . C1 C 0.2164(3) 0.0061(2) 0.3837(6) 0.0297(11) Uani 1 1 d . . . C2 C 0.3126(3) 0.0282(2) 0.4881(6) 0.0313(11) Uani 1 1 d . . . C3 C 0.3461(3) 0.10022(19) 0.2772(6) 0.0300(11) Uani 1 1 d . . . C4 C 0.4185(3) 0.13698(18) 0.1958(6) 0.0300(11) Uani 1 1 d . . . C5 C 0.5195(3) 0.1386(2) 0.2676(6) 0.0363(12) Uani 1 1 d . . . H5 H 0.5397 0.1152 0.3727 0.044 Uiso 1 1 calc R . . C6 C 0.5897(4) 0.1735(2) 0.1889(6) 0.0392(12) Uani 1 1 d . . . H6 H 0.6577 0.1740 0.2388 0.047 Uiso 1 1 calc R . . C7 C 0.5599(4) 0.2077(2) 0.0361(7) 0.0428(13) Uani 1 1 d . . . H7 H 0.6082 0.2314 -0.0195 0.051 Uiso 1 1 calc R . . C8 C 0.4612(4) 0.2080(2) -0.0365(6) 0.0390(12) Uani 1 1 d . . . H8 H 0.4424 0.2323 -0.1407 0.047 Uiso 1 1 calc R . . C9 C 0.3886(3) 0.1731(2) 0.0405(6) 0.0305(11) Uani 1 1 d . . . C10 C 0.2830(3) 0.17314(19) -0.0318(6) 0.0323(11) Uani 1 1 d . . . C11 C 0.2465(4) 0.2102(2) -0.1774(6) 0.0410(13) Uani 1 1 d . . . H11 H 0.2916 0.2364 -0.2337 0.049 Uiso 1 1 calc R . . C12 C 0.1467(4) 0.2097(2) -0.2420(6) 0.0416(13) Uani 1 1 d . . . H12 H 0.1236 0.2349 -0.3425 0.050 Uiso 1 1 calc R . . C13 C 0.0797(4) 0.1720(2) -0.1593(6) 0.0366(12) Uani 1 1 d . . . H13 H 0.0107 0.1724 -0.2026 0.044 Uiso 1 1 calc R . . C14 C 0.1121(3) 0.1349(2) -0.0177(6) 0.0341(11) Uani 1 1 d . . . H14 H 0.0659 0.1089 0.0366 0.041 Uiso 1 1 calc R . . C15 C 0.2150(3) 0.13483(19) 0.0497(5) 0.0295(11) Uani 1 1 d . . . C16 C 0.2508(3) 0.09744(19) 0.2013(6) 0.0289(11) Uani 1 1 d . . . C17 C 0.1366(3) -0.0766(2) 0.5159(6) 0.0326(11) Uani 1 1 d . . . C18 C 0.0874(4) -0.1113(2) 0.6347(6) 0.0428(13) Uani 1 1 d . . . H18 H 0.0512 -0.0895 0.7167 0.051 Uiso 1 1 calc R . . C19 C 0.0925(4) -0.1784(3) 0.6308(8) 0.0555(16) Uani 1 1 d . . . H19 H 0.0578 -0.2030 0.7097 0.067 Uiso 1 1 calc R . . C20 C 0.1458(5) -0.2105(3) 0.5169(8) 0.0555(16) Uani 1 1 d . . . H20 H 0.1486 -0.2569 0.5184 0.067 Uiso 1 1 calc R . . C21 C 0.1965(4) -0.1757(2) 0.3978(7) 0.0444(13) Uani 1 1 d . . . H21 H 0.2345 -0.1977 0.3189 0.053 Uiso 1 1 calc R . . C22 C 0.1898(4) -0.1079(2) 0.3981(6) 0.0364(12) Uani 1 1 d . . . C23 C 0.2291(4) -0.0587(2) 0.2759(6) 0.0339(11) Uani 1 1 d . . . C2A C 0.1149(4) 0.0367(2) 0.6244(6) 0.0427(13) Uani 1 1 d . . . H2A1 H 0.1149 0.0814 0.5779 0.064 Uiso 1 1 calc R . . H2A2 H 0.1651 0.0331 0.7272 0.064 Uiso 1 1 calc R . . H2A3 H 0.0486 0.0266 0.6585 0.064 Uiso 1 1 calc R . . C2B C 0.4141(4) 0.0191(2) 0.7604(6) 0.0457(14) Uani 1 1 d . . . H2B1 H 0.4180 -0.0055 0.8707 0.069 Uiso 1 1 calc R . . H2B2 H 0.4076 0.0658 0.7847 0.069 Uiso 1 1 calc R . . H2B3 H 0.4751 0.0116 0.7044 0.069 Uiso 1 1 calc R . . C23A C 0.1590(4) -0.0567(2) 0.1027(6) 0.0464(14) Uani 1 1 d . . . H23A H 0.1836 -0.0242 0.0240 0.070 Uiso 1 1 calc R . . H23B H 0.0914 -0.0447 0.1268 0.070 Uiso 1 1 calc R . . H23C H 0.1574 -0.0998 0.0468 0.070 Uiso 1 1 calc R . . C23B C 0.3361(4) -0.0719(2) 0.2378(7) 0.0452(13) Uani 1 1 d . . . H23D H 0.3590 -0.0358 0.1684 0.068 Uiso 1 1 calc R . . H23E H 0.3382 -0.1128 0.1718 0.068 Uiso 1 1 calc R . . H23F H 0.3799 -0.0755 0.3488 0.068 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.036(2) 0.034(2) 0.033(2) 0.0022(17) 0.0044(19) 0.0004(18) N2 0.028(2) 0.032(2) 0.029(2) 0.0013(17) 0.0128(18) -0.0019(16) O1 0.0290(17) 0.0346(16) 0.0366(18) 0.0076(14) 0.0043(15) -0.0010(14) O2 0.0314(18) 0.0427(17) 0.0318(17) 0.0053(15) 0.0002(15) -0.0069(14) C1 0.026(3) 0.029(2) 0.034(3) 0.005(2) 0.005(2) 0.0043(19) C2 0.032(3) 0.030(2) 0.033(3) 0.003(2) 0.007(2) 0.003(2) C3 0.034(3) 0.025(2) 0.032(3) 0.0027(19) 0.007(2) -0.0015(19) C4 0.032(3) 0.023(2) 0.036(3) -0.002(2) 0.006(2) 0.001(2) C5 0.033(3) 0.035(2) 0.041(3) 0.004(2) 0.006(2) 0.002(2) C6 0.035(3) 0.040(3) 0.044(3) -0.004(2) 0.007(3) -0.004(2) C7 0.041(3) 0.039(3) 0.051(3) 0.004(2) 0.015(3) -0.008(2) C8 0.041(3) 0.037(3) 0.041(3) 0.005(2) 0.011(3) -0.001(2) C9 0.029(3) 0.030(2) 0.035(3) 0.001(2) 0.008(2) 0.001(2) C10 0.034(3) 0.027(2) 0.036(3) 0.004(2) 0.008(2) 0.000(2) C11 0.047(3) 0.038(3) 0.039(3) 0.014(2) 0.007(3) -0.001(2) C12 0.043(3) 0.039(3) 0.042(3) 0.012(2) 0.002(3) 0.003(2) C13 0.037(3) 0.036(2) 0.035(3) 0.001(2) -0.002(2) 0.002(2) C14 0.033(3) 0.034(2) 0.036(3) -0.002(2) 0.005(2) 0.000(2) C15 0.033(3) 0.027(2) 0.028(2) -0.003(2) 0.003(2) 0.001(2) C16 0.028(3) 0.029(2) 0.030(3) 0.0003(19) 0.008(2) -0.0043(19) C17 0.028(3) 0.036(2) 0.034(3) 0.005(2) 0.006(2) 0.001(2) C18 0.041(3) 0.054(3) 0.034(3) 0.010(2) 0.008(3) -0.009(2) C19 0.064(4) 0.047(3) 0.052(4) 0.018(3) -0.004(3) -0.022(3) C20 0.072(4) 0.039(3) 0.052(4) 0.005(3) -0.008(3) -0.015(3) C21 0.049(3) 0.037(3) 0.045(3) -0.002(2) -0.005(3) 0.000(2) C22 0.039(3) 0.035(2) 0.033(3) 0.005(2) -0.004(2) -0.003(2) C23 0.039(3) 0.035(2) 0.028(3) -0.001(2) 0.004(2) -0.005(2) C2A 0.038(3) 0.050(3) 0.041(3) -0.005(2) 0.009(3) 0.002(2) C2B 0.045(3) 0.051(3) 0.039(3) 0.003(2) -0.006(3) -0.007(2) C23A 0.061(4) 0.044(3) 0.033(3) -0.003(2) 0.001(3) -0.003(2) C23B 0.040(3) 0.049(3) 0.049(3) -0.006(2) 0.018(3) 0.007(2) _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 N1 C2 1.280(5) . ? N1 C3 1.414(5) . ? N2 C17 1.393(5) . ? N2 C1 1.427(6) . ? N2 C2A 1.464(6) . ? O1 C16 1.384(5) . ? O1 C1 1.441(5) . ? O2 C2 1.349(5) . ? O2 C2B 1.444(5) . ? C1 C2 1.510(6) . ? C1 C23 1.582(6) . ? C3 C16 1.347(6) . ? C3 C4 1.429(6) . ? C4 C5 1.405(6) . ? C4 C9 1.420(6) . ? C5 C6 1.377(7) . ? C6 C7 1.384(7) . ? C7 C8 1.379(7) . ? C8 C9 1.395(6) . ? C9 C10 1.464(6) . ? C10 C11 1.391(6) . ? C10 C15 1.405(6) . ? C11 C12 1.377(6) . ? C12 C13 1.391(7) . ? C13 C14 1.355(6) . ? C14 C15 1.420(6) . ? C15 C16 1.428(6) . ? C17 C22 1.373(7) . ? C17 C18 1.382(6) . ? C18 C19 1.373(7) . ? C19 C20 1.362(8) . ? C20 C21 1.396(7) . ? C21 C22 1.390(6) . ? C22 C23 1.511(6) . ? C23 C23B 1.525(7) . ? C23 C23A 1.539(6) . ? 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 C2 N1 C3 114.8(4) . . ? C17 N2 C1 109.4(3) . . ? C17 N2 C2A 121.5(4) . . ? C1 N2 C2A 119.6(3) . . ? C16 O1 C1 117.0(3) . . ? C2 O2 C2B 115.8(3) . . ? N2 C1 O1 106.2(3) . . ? N2 C1 C2 113.8(4) . . ? O1 C1 C2 106.8(3) . . ? N2 C1 C23 103.9(3) . . ? O1 C1 C23 113.2(3) . . ? C2 C1 C23 113.0(4) . . ? N1 C2 O2 121.5(4) . . ? N1 C2 C1 126.9(4) . . ? O2 C2 C1 111.6(4) . . ? C16 C3 N1 121.3(4) . . ? C16 C3 C4 119.7(4) . . ? N1 C3 C4 119.0(4) . . ? C5 C4 C9 118.9(4) . . ? C5 C4 C3 121.2(4) . . ? C9 C4 C3 119.9(4) . . ? C6 C5 C4 121.4(4) . . ? C5 C6 C7 119.1(5) . . ? C8 C7 C6 121.0(5) . . ? C7 C8 C9 121.0(4) . . ? C8 C9 C4 118.5(4) . . ? C8 C9 C10 122.4(4) . . ? C4 C9 C10 119.1(4) . . ? C11 C10 C15 118.2(4) . . ? C11 C10 C9 122.8(4) . . ? C15 C10 C9 119.0(4) . . ? C12 C11 C10 121.6(5) . . ? C11 C12 C13 119.7(4) . . ? C14 C13 C12 120.7(4) . . ? C13 C14 C15 120.1(4) . . ? C10 C15 C14 119.6(4) . . ? C10 C15 C16 119.0(4) . . ? C14 C15 C16 121.3(4) . . ? C3 C16 O1 120.8(4) . . ? C3 C16 C15 123.0(4) . . ? O1 C16 C15 116.1(4) . . ? C22 C17 C18 121.3(4) . . ? C22 C17 N2 110.0(4) . . ? C18 C17 N2 128.7(4) . . ? C19 C18 C17 118.0(5) . . ? C20 C19 C18 121.8(5) . . ? C19 C20 C21 120.4(5) . . ? C22 C21 C20 118.1(5) . . ? C17 C22 C21 120.3(5) . . ? C17 C22 C23 110.1(4) . . ? C21 C22 C23 129.5(5) . . ? C22 C23 C23B 114.0(4) . . ? C22 C23 C23A 109.2(4) . . ? C23B C23 C23A 109.7(4) . . ? C22 C23 C1 99.7(4) . . ? C23B C23 C1 114.2(4) . . ? C23A C23 C1 109.6(4) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.225 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.060 #*********************************************************************** data_4 _database_code_CSD 171835 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24H23N3O4' _chemical_formula_weight 417.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.3622(9) _cell_length_b 15.3310(15) _cell_length_c 13.5407(12) _cell_angle_alpha 90.00 _cell_angle_beta 103.856(10) _cell_angle_gamma 90.00 _cell_volume 2088.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 4.8 _cell_measurement_theta_max 52.0 _exptl_crystal_description 'hexagonal plate' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type semi-empirical #(DIFABS - N. Walker and D. Stuart, Acta Crystallogr., Sect A 1983, 39, #158-166) _exptl_absorpt_correction_T_min 0.52 _exptl_absorpt_correction_T_max 0.85 _exptl_special_details ; The data was collected at low temperature (T=180K) on a STOE imaging plate diffraction system (I.P.D.S), equipped with an Oxford cryosystems cooler device, the crystal-to-detector distance was 70mm, 143 exposures were obtained with 0<(<200° and with the crystal rotated through 1.4° in (. Coverage of the unique set has been 94.1% complete to at least 26.05°. Crystal decay was monitored by measuring 200 reflections by image. The final unit cell parameters was obtained by the least-squares refinement of 5000 reflections. Any significant fluctuations in the intensity monitors were observed during the data collection. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\( _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type ; Stoe and Cie (1996) IPDS Manual. Version 2.75. Stoe and Cie, Darmstadt, Germany. ; #_diffrn_measurement_method rotation en ( #_diffrn_detector_area_resol_mean 2( (3.3 -52.1) #_d(hkl) range (12.453 - 0.809)Å _diffrn_standards_number 200 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16036 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 26.15 _reflns_number_total 3872 _reflns_number_gt 3020 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Stoe and Cie (1996) IPDS Manual. Version 2.75 Stoe and Cie, Darmstadt, Germany ; _computing_cell_refinement ; Stoe and Cie (1996) IPDS Manual. Version 2.75 Stoe and Cie, Darmstadt, Germany. ; _computing_data_reduction ; Stoe and Cie (1996) IPDS Manual. Version 2.75 Stoe and Cie, Darmstadt, Germany ; _computing_structure_solution ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Zsolnai,L.(1997). ZORTEP.Molecular Graphics Program.University of Heidelberg, Germany ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0724P)^2^+0.1250P] 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_number_reflns 3872 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1088 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.88995(10) 0.01891(6) 0.60611(8) 0.0313(2) Uani 1 1 d . . . O2 O 0.81430(11) 0.05955(6) 0.84123(7) 0.0351(3) Uani 1 1 d . . . O3 O 0.52393(13) 0.43396(8) 0.67983(11) 0.0555(3) Uani 1 1 d . . . O4 O 0.68567(12) 0.49568(7) 0.78649(9) 0.0454(3) Uani 1 1 d . . . N1 N 0.93567(12) 0.13752(7) 0.71301(9) 0.0301(3) Uani 1 1 d . . . N2 N 0.76955(12) -0.06459(7) 0.74467(9) 0.0301(3) Uani 1 1 d . . . N3 N 0.63775(13) 0.43309(7) 0.73395(10) 0.0336(3) Uani 1 1 d . . . C1 C 0.83539(14) 0.07293(8) 0.67209(10) 0.0274(3) Uani 1 1 d . . . C2 C 0.80418(14) 0.01481(8) 0.75472(10) 0.0285(3) Uani 1 1 d . . . C3 C 0.76781(14) -0.10164(8) 0.64915(10) 0.0278(3) Uani 1 1 d . . . C4 C 0.70763(14) -0.18450(8) 0.62332(10) 0.0293(3) Uani 1 1 d . . . C5 C 0.63558(15) -0.22734(9) 0.68511(12) 0.0361(3) Uani 1 1 d . . . H5 H 0.6247 -0.2001 0.7456 0.043 Uiso 1 1 calc R . . C6 C 0.58121(17) -0.30778(10) 0.65857(13) 0.0430(4) Uani 1 1 d . . . H6 H 0.5330 -0.3360 0.7009 0.052 Uiso 1 1 calc R . . C7 C 0.59592(17) -0.34919(10) 0.56908(13) 0.0438(4) Uani 1 1 d . . . H7 H 0.5582 -0.4052 0.5515 0.053 Uiso 1 1 calc R . . C8 C 0.66430(16) -0.30890(10) 0.50768(12) 0.0393(4) Uani 1 1 d . . . H8 H 0.6734 -0.3372 0.4473 0.047 Uiso 1 1 calc R . . C9 C 0.72194(15) -0.22573(9) 0.53234(11) 0.0324(3) Uani 1 1 d . . . C10 C 0.79424(16) -0.18296(10) 0.46996(11) 0.0362(3) Uani 1 1 d . . . H10 H 0.8060 -0.2110 0.4102 0.043 Uiso 1 1 calc R . . C11 C 0.84714(15) -0.10225(9) 0.49431(11) 0.0334(3) Uani 1 1 d . . . H11 H 0.8943 -0.0738 0.4514 0.040 Uiso 1 1 calc R . . C12 C 0.83125(14) -0.06162(8) 0.58320(11) 0.0281(3) Uani 1 1 d . . . C13 C 0.71154(14) 0.12814(8) 0.61596(10) 0.0296(3) Uani 1 1 d . . . C14 C 0.74088(14) 0.21290(8) 0.67382(10) 0.0278(3) Uani 1 1 d . . . C15 C 0.66125(15) 0.28402(9) 0.67552(10) 0.0301(3) Uani 1 1 d . . . H15 H 0.5709 0.2844 0.6386 0.036 Uiso 1 1 calc R . . C16 C 0.71761(14) 0.35594(8) 0.73354(10) 0.0287(3) Uani 1 1 d . . . C17 C 0.84853(15) 0.35675(9) 0.78854(11) 0.0318(3) Uani 1 1 d . . . H17 H 0.8832 0.4065 0.8278 0.038 Uiso 1 1 calc R . . C18 C 0.92894(15) 0.28523(9) 0.78639(11) 0.0332(3) Uani 1 1 d . . . H18 H 1.0190 0.2847 0.8239 0.040 Uiso 1 1 calc R . . C19 C 0.87384(14) 0.21403(8) 0.72752(10) 0.0282(3) Uani 1 1 d . . . C20 C 1.06334(15) 0.11240(10) 0.77667(13) 0.0386(4) Uani 1 1 d . . . H20A H 1.0891 0.0554 0.7548 0.058 Uiso 1 1 calc R . . H20B H 1.0571 0.1089 0.8477 0.058 Uiso 1 1 calc R . . H20C H 1.1303 0.1559 0.7706 0.058 Uiso 1 1 calc R . . C21 C 0.57868(16) 0.08730(10) 0.61966(13) 0.0391(4) Uani 1 1 d . . . H21A H 0.5697 0.0306 0.5854 0.059 Uiso 1 1 calc R . . H21B H 0.5062 0.1257 0.5853 0.059 Uiso 1 1 calc R . . H21C H 0.5748 0.0794 0.6907 0.059 Uiso 1 1 calc R . . C22 C 0.71697(19) 0.14357(10) 0.50514(11) 0.0427(4) Uani 1 1 d . . . H22A H 0.7040 0.0881 0.4682 0.064 Uiso 1 1 calc R . . H22B H 0.8037 0.1680 0.5033 0.064 Uiso 1 1 calc R . . H22C H 0.6466 0.1845 0.4732 0.064 Uiso 1 1 calc R . . C23 C 0.78399(18) 0.01253(10) 0.92561(11) 0.0407(4) Uani 1 1 d . . . H23A H 0.8445 -0.0379 0.9443 0.049 Uiso 1 1 calc R . . H23B H 0.6914 -0.0092 0.9070 0.049 Uiso 1 1 calc R . . C24 C 0.8019(3) 0.07472(13) 1.01230(14) 0.0620(6) Uani 1 1 d . . . H24A H 0.7836 0.0448 1.0715 0.093 Uiso 1 1 calc R . . H24B H 0.7403 0.1238 0.9932 0.093 Uiso 1 1 calc R . . H24C H 0.8935 0.0965 1.0292 0.093 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0354(6) 0.0278(5) 0.0342(5) -0.0036(4) 0.0155(5) -0.0017(4) O2 0.0457(7) 0.0349(5) 0.0268(5) -0.0054(4) 0.0131(5) -0.0054(4) O3 0.0369(8) 0.0476(7) 0.0731(9) -0.0119(6) -0.0041(7) 0.0107(5) O4 0.0474(7) 0.0311(5) 0.0559(7) -0.0100(5) 0.0091(6) 0.0006(5) N1 0.0256(6) 0.0294(6) 0.0341(6) -0.0022(5) 0.0046(5) -0.0008(4) N2 0.0317(7) 0.0314(6) 0.0277(6) -0.0015(4) 0.0079(5) -0.0012(5) N3 0.0353(8) 0.0304(6) 0.0355(7) 0.0000(5) 0.0095(6) 0.0003(5) C1 0.0287(8) 0.0279(6) 0.0267(7) -0.0032(5) 0.0084(6) -0.0006(5) C2 0.0281(7) 0.0304(7) 0.0270(7) -0.0026(5) 0.0065(6) -0.0001(5) C3 0.0270(7) 0.0292(6) 0.0267(7) -0.0005(5) 0.0053(6) 0.0028(5) C4 0.0274(7) 0.0272(6) 0.0304(7) 0.0007(5) 0.0013(6) 0.0034(5) C5 0.0348(8) 0.0355(7) 0.0369(8) 0.0014(6) 0.0067(7) -0.0019(6) C6 0.0406(10) 0.0387(8) 0.0489(9) 0.0044(7) 0.0090(8) -0.0067(6) C7 0.0422(10) 0.0314(7) 0.0517(10) -0.0032(7) -0.0008(8) -0.0059(6) C8 0.0389(9) 0.0340(7) 0.0396(8) -0.0066(6) -0.0015(8) 0.0019(6) C9 0.0304(8) 0.0313(7) 0.0319(7) -0.0014(5) 0.0005(7) 0.0039(5) C10 0.0422(9) 0.0359(7) 0.0303(7) -0.0053(6) 0.0080(7) 0.0049(6) C11 0.0358(9) 0.0354(7) 0.0309(7) -0.0001(6) 0.0117(7) 0.0037(6) C12 0.0271(7) 0.0267(6) 0.0293(7) -0.0005(5) 0.0044(6) 0.0016(5) C13 0.0301(8) 0.0292(7) 0.0280(7) -0.0023(5) 0.0038(6) 0.0009(5) C14 0.0304(8) 0.0290(6) 0.0242(6) 0.0010(5) 0.0067(6) -0.0016(5) C15 0.0279(7) 0.0331(7) 0.0286(7) 0.0009(5) 0.0055(6) 0.0001(5) C16 0.0324(8) 0.0267(6) 0.0284(7) 0.0014(5) 0.0097(6) 0.0007(5) C17 0.0343(8) 0.0288(7) 0.0314(7) -0.0019(5) 0.0063(7) -0.0046(5) C18 0.0279(8) 0.0322(7) 0.0371(8) -0.0019(6) 0.0034(7) -0.0036(5) C19 0.0289(8) 0.0271(6) 0.0292(7) 0.0000(5) 0.0081(6) -0.0008(5) C20 0.0296(8) 0.0365(8) 0.0467(9) -0.0033(6) 0.0034(8) 0.0025(6) C21 0.0281(8) 0.0364(8) 0.0494(9) -0.0069(6) 0.0028(8) -0.0006(6) C22 0.0552(11) 0.0421(8) 0.0279(7) -0.0002(6) 0.0041(8) 0.0075(7) C23 0.0491(10) 0.0453(8) 0.0305(8) -0.0002(6) 0.0149(8) -0.0034(7) C24 0.0912(16) 0.0642(12) 0.0360(9) -0.0114(8) 0.0261(11) -0.0025(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 O1 C12 1.3784(16) . ? O1 C1 1.4303(15) . ? O2 C2 1.3397(16) . ? O2 C23 1.4477(17) . ? O3 N3 1.2305(18) . ? O4 N3 1.2265(16) . ? N1 C19 1.3731(17) . ? N1 C1 1.4463(18) . ? N1 C20 1.448(2) . ? N2 C2 1.2671(18) . ? N2 C3 1.4088(17) . ? N3 C16 1.4445(17) . ? C1 C2 1.5243(18) . ? C1 C13 1.573(2) . ? C3 C12 1.3737(19) . ? C3 C4 1.4215(19) . ? C4 C5 1.410(2) . ? C4 C9 1.4236(19) . ? C5 C6 1.368(2) . ? C5 H5 0.9500 . ? C6 C7 1.408(2) . ? C6 H6 0.9500 . ? C7 C8 1.363(2) . ? C7 H7 0.9500 . ? C8 C9 1.414(2) . ? C8 H8 0.9500 . ? C9 C10 1.417(2) . ? C10 C11 1.361(2) . ? C10 H10 0.9500 . ? C11 C12 1.3996(19) . ? C11 H11 0.9500 . ? C13 C14 1.5102(18) . ? C13 C21 1.524(2) . ? C13 C22 1.533(2) . ? C14 C15 1.3709(19) . ? C14 C19 1.396(2) . ? C15 C16 1.398(2) . ? C15 H15 0.9500 . ? C16 C17 1.382(2) . ? C17 C18 1.382(2) . ? C17 H17 0.9500 . ? C18 C19 1.391(2) . ? C18 H18 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.489(2) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 C12 O1 C1 116.10(10) . . ? C2 O2 C23 116.67(11) . . ? C19 N1 C1 108.83(11) . . ? C19 N1 C20 122.23(12) . . ? C1 N1 C20 121.09(11) . . ? C2 N2 C3 115.28(11) . . ? O4 N3 O3 122.29(12) . . ? O4 N3 C16 119.35(13) . . ? O3 N3 C16 118.34(12) . . ? O1 C1 N1 106.29(10) . . ? O1 C1 C2 107.76(10) . . ? N1 C1 C2 112.23(11) . . ? O1 C1 C13 114.12(11) . . ? N1 C1 C13 104.18(10) . . ? C2 C1 C13 112.16(11) . . ? N2 C2 O2 123.14(12) . . ? N2 C2 C1 125.95(12) . . ? O2 C2 C1 110.89(11) . . ? C12 C3 N2 120.92(12) . . ? C12 C3 C4 119.29(12) . . ? N2 C3 C4 119.65(12) . . ? C5 C4 C3 122.26(13) . . ? C5 C4 C9 119.10(13) . . ? C3 C4 C9 118.64(12) . . ? C6 C5 C4 120.49(14) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 120.67(15) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 119.99(14) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 121.11(14) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C8 C9 C10 122.03(13) . . ? C8 C9 C4 118.64(13) . . ? C10 C9 C4 119.33(13) . . ? C11 C10 C9 121.06(13) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 119.30(13) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C3 C12 O1 120.52(12) . . ? C3 C12 C11 122.24(13) . . ? O1 C12 C11 117.11(12) . . ? C14 C13 C21 114.06(11) . . ? C14 C13 C22 108.96(11) . . ? C21 C13 C22 109.92(13) . . ? C14 C13 C1 99.95(11) . . ? C21 C13 C1 113.70(11) . . ? C22 C13 C1 109.81(11) . . ? C15 C14 C19 120.29(13) . . ? C15 C14 C13 130.23(14) . . ? C19 C14 C13 109.39(12) . . ? C14 C15 C16 117.69(14) . . ? C14 C15 H15 121.2 . . ? C16 C15 H15 121.2 . . ? C17 C16 C15 122.27(13) . . ? C17 C16 N3 118.67(12) . . ? C15 C16 N3 119.04(13) . . ? C18 C17 C16 120.02(13) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 117.91(14) . . ? C17 C18 H18 121.0 . . ? C19 C18 H18 121.0 . . ? N1 C19 C18 127.65(13) . . ? N1 C19 C14 110.55(12) . . ? C18 C19 C14 121.80(13) . . ? N1 C20 H20A 109.5 . . ? N1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C13 C21 H21A 109.5 . . ? C13 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C13 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C13 C22 H22A 109.5 . . ? C13 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C13 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O2 C23 C24 107.09(13) . . ? O2 C23 H23A 110.3 . . ? C24 C23 H23A 110.3 . . ? O2 C23 H23B 110.3 . . ? C24 C23 H23B 110.3 . . ? H23A C23 H23B 108.6 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 26.15 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.241 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.039 #===========================END=======================================