# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global #============================================================================== # 3. TITLE AND AUTHOR LIST _journal_coden_Cambridge 182 loop_ _publ_author_name 'Troels Skrydstrup' 'Silvia Albu' 'Rita G. Hazell' 'Sine A. Johannesen' _publ_contact_author_name 'Prof Troels Skrydstrup' _publ_contact_author_address ; Chemistry University of Aarhus Langelandsgade 140 Aarhus 8000 C DENMARK ; _publ_contact_author_email TS@CHEM.AU.DK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Radical addition of nitrones to acrylates mediated by SmI2: asymmetric synthesis of gamma-amino acids employing carbohydrate-based chiral auxiliaries. ; #============================================================================== _publ_section_references ; Altomare,A., Cascarano,G., Giacovazzo,C., Guagliardi,A., Moliterni,.A,G,G., Burla,M.C., Polidori,G., Camalli,M. & Spagna,R. (1997). SIR97. University of Bari, Italy. Becker,P.J. & Coppens, P. (1974). Acta Cryst. A30, 129-153. Burnett,M.N. & Johnson,C.K. (1996). ORTEP-III. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Busing,W.R., Martin,K.O. & Levy,H.A. (1962). ORFLS. Report ORNL-TM-305. Oak Ridge National Laboratory, Tennessee, USA. Hazell,A. (1995). KRYSTAL, An integrated system of crystallographic programs. Aarhus University, Denmark. Siemens (1995) SMART, SAINT and XPREP Area-Detector Control and Integration Software. Siemens Analytical X-ray Instruments Inc. Madison, Wisconsin, USA. ; #============================================================================== data_sine2b _database_code_depnum_ccdc_archive 'CCDC 236553' #=================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (R)-N-(3-buthoxycarbonyl-1-isopropyl)-2,3:5,6-bis-O- isopropylidene-D-mannose-imine N-oxide ; _chemical_formula_sum 'C23 H41 N O8' _chemical_formula_moiety 'C23 H41 N O8' _chemical_formula_weight 459.57 #=================================== # 6. CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,-y,1/2+z -x,1/2+y,1/2-z 1/2+x,1/2-y,-z _cell_length_a 6.540(7) _cell_length_b 19.97(2) _cell_length_c 20.00(2) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 2612(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120 _cell_measurement_reflns_used 4994 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 26.61 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_process_details none #=================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'x-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation scans with narrow frames' _diffrn_standards_decay_% 0 _diffrn_reflns_number 45712 _diffrn_reflns_av_R_equivalents 0.19 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 26.61 _diffrn_reflns_reduction_process 45712 _reflns_number_total 3145 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_theta_full 26.61 _reflns_number_gt 1922 _reflns_threshold_expression I>3\s(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution ; SIR97 (Altomare et al., 1997 ), KRYSTAL ; _computing_structure_refinement 'modified ORFLS(1962), KRYSTAL' _computing_molecular_graphics ; ORTEP-III (Burnett & Johnson, 1996), KRYSTAL ; _computing_publication_material KRYSTAL _atom_type_scat_source IntTabIV #=================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w= 1/{[\s~cs~(F^2^)+B+(1+A)F^2^]^1/2^- |F|}^2^ where A = 0.03 and B = 0.0 ; _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method ; Type 1 Lorentzian isotropic ( Becker and Coppens, 1974) ; _refine_ls_extinction_coef 524(48) _refine_ls_number_reflns 1922 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_gt 0.049 _refine_ls_wR_factor_ref 0.047 _refine_ls_goodness_of_fit_ref 1.235 _refine_ls_shift/su_max 0.00019 _refine_ls_shift/su_mean 0.00003 _refine_diff_density_max 0.28(6) _refine_diff_density_min -0.24(6) #========================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type O1 0.4986(4) 0.0818(1) 0.1601(1) 0.033(2) Uij O2 0.9671(4) 0.1636(1) 0.2658(1) 0.032(2) Uij O3 1.1061(4) 0.1993(1) 0.1695(1) 0.026(2) Uij O4 1.0997(4) 0.0594(1) 0.1357(1) 0.025(2) Uij O5 0.9746(4) 0.1819(1) 0.0058(1) 0.027(2) Uij O6 0.9389(4) 0.0820(1) -0.0486(1) 0.028(2) Uij O7 0.0130(5) -0.0303(2) 0.3311(1) 0.038(2) Uij O8 0.1472(4) 0.0421(1) 0.4049(1) 0.032(2) Uij N 0.6175(5) 0.0466(2) 0.1993(2) 0.023(2) Uij C1 0.7796(6) 0.0727(2) 0.2258(2) 0.022(2) Uij C2 0.8228(5) 0.1441(2) 0.2152(2) 0.024(2) Uij C3 0.9252(6) 0.1654(2) 0.1488(2) 0.023(2) Uij C4 0.9822(6) 0.1089(2) 0.1026(2) 0.021(2) Uij C5 1.0954(6) 0.1336(2) 0.0411(2) 0.024(2) Uij C6 1.1240(7) 0.0783(2) -0.0107(2) 0.031(3) Uij C7 0.5587(6) -0.0243(2) 0.2121(2) 0.024(2) Uij C8 0.3542(6) -0.0273(2) 0.2486(2) 0.025(2) Uij C9 0.3522(6) 0.0120(2) 0.3139(2) 0.029(3) Uij C10 0.1528(7) 0.0048(2) 0.3498(2) 0.029(3) Uij C11 -0.0390(7) 0.0392(2) 0.4448(2) 0.041(3) Uij C12 -0.1820(7) 0.0940(3) 0.4254(2) 0.044(3) Uij C13 -0.1047(9) 0.1634(3) 0.4389(2) 0.055(4) Uij C14 -0.2557(12) 0.2178(3) 0.4216(3) 0.099(5) Uij C15 0.5622(6) -0.0616(2) 0.1453(2) 0.030(3) Uij C16 0.7811(7) -0.0716(2) 0.1209(2) 0.039(3) Uij C17 0.4497(8) -0.1266(2) 0.1475(3) 0.060(4) Uij C18 0.8902(6) 0.1517(2) -0.0529(2) 0.026(2) Uij C19 0.6604(6) 0.1581(2) -0.0511(2) 0.036(3) Uij C20 0.9847(7) 0.1829(2) -0.1136(2) 0.039(3) Uij C21 1.0862(7) 0.2170(2) 0.2376(2) 0.030(3) Uij C22 1.2915(7) 0.2152(2) 0.2701(2) 0.038(3) Uij C23 0.9770(7) 0.2832(2) 0.2455(2) 0.043(3) Uij H4o 1.2089 0.0789 0.1532 0.027 Uiso H1 0.8701 0.0459 0.2515 0.026 Uiso H2 0.7002 0.1690 0.2212 0.028 Uiso H3 0.8383 0.1958 0.1259 0.028 Uiso H4 0.8590 0.0885 0.0880 0.025 Uiso H5 1.2239 0.1522 0.0532 0.028 Uiso H6a 1.2398 0.0869 -0.0381 0.038 Uiso H6b 1.1383 0.0359 0.0100 0.038 Uiso H7 0.6599 -0.0437 0.2402 0.029 Uiso H8a 0.3243 -0.0728 0.2585 0.031 Uiso H8b 0.2515 -0.0096 0.2202 0.031 Uiso H9a 0.3743 0.0580 0.3043 0.034 Uiso H9b 0.4586 -0.0041 0.3419 0.034 Uiso H11a -0.0046 0.0437 0.4908 0.049 Uiso H11b -0.1040 -0.0028 0.4378 0.049 Uiso H12a -0.3059 0.0881 0.4497 0.052 Uiso H12b -0.2088 0.0903 0.3789 0.052 Uiso H13a 0.0157 0.1701 0.4133 0.066 Uiso H13b -0.0732 0.1668 0.4851 0.066 Uiso H14a -0.2062 0.2617 0.4300 0.118 Uiso H14b -0.3759 0.2110 0.4471 0.118 Uiso H14c -0.2870 0.2143 0.3753 0.118 Uiso H15 0.4954 -0.0338 0.1136 0.036 Uiso H16a 0.7832 -0.0947 0.0795 0.045 Uiso H16b 0.8544 -0.0969 0.1532 0.045 Uiso H16c 0.8441 -0.0291 0.1155 0.045 Uiso H17a 0.4518 -0.1497 0.1058 0.072 Uiso H17b 0.3112 -0.1179 0.1590 0.072 Uiso H17c 0.5103 -0.1543 0.1804 0.072 Uiso H19a 0.6043 0.1380 -0.0901 0.042 Uiso H19b 0.6238 0.2041 -0.0499 0.042 Uiso H19c 0.6086 0.1362 -0.0125 0.042 Uiso H20a 0.9284 0.1627 -0.1527 0.046 Uiso H20b 1.1282 0.1760 -0.1130 0.046 Uiso H20c 0.9563 0.2295 -0.1141 0.046 Uiso H22a 1.3705 0.2503 0.2514 0.047 Uiso H22b 1.3559 0.1732 0.2617 0.047 Uiso H22c 1.2779 0.2214 0.3169 0.047 Uiso H23a 1.0555 0.3184 0.2269 0.052 Uiso H23b 0.9558 0.2917 0.2919 0.052 Uiso H23c 0.8482 0.2811 0.2236 0.052 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.016(1) 0.041(2) 0.043(2) 0.001(1) -0.008(2) 0.015(2) O2 0.029(2) 0.048(2) 0.020(2) -0.017(2) 0.003(1) -0.003(1) O3 0.021(1) 0.034(2) 0.023(2) -0.009(1) 0.002(1) -0.005(1) O4 0.013(1) 0.028(2) 0.035(2) 0.000(1) -0.009(1) 0.004(1) O5 0.031(2) 0.024(2) 0.025(2) -0.001(1) -0.006(1) -0.001(1) O6 0.025(2) 0.027(2) 0.031(2) 0.001(1) -0.005(1) -0.007(1) O7 0.027(2) 0.050(2) 0.038(2) -0.006(2) 0.007(2) 0.002(2) O8 0.030(2) 0.035(2) 0.032(2) 0.003(1) 0.009(1) 0.001(2) N 0.012(2) 0.033(2) 0.024(2) 0.002(2) 0.002(2) 0.005(2) C1 0.012(2) 0.035(3) 0.018(2) 0.001(2) 0.004(2) -0.002(2) C2 0.013(2) 0.029(3) 0.028(3) 0.001(2) 0.005(2) -0.006(2) C3 0.015(2) 0.028(2) 0.026(2) 0.002(2) -0.003(2) 0.001(2) C4 0.011(2) 0.027(2) 0.024(2) 0.000(2) -0.005(2) 0.002(2) C5 0.016(2) 0.029(2) 0.027(3) -0.003(2) 0.000(2) -0.001(2) C6 0.026(2) 0.039(3) 0.029(3) 0.004(2) -0.001(2) -0.004(2) C7 0.019(2) 0.025(2) 0.029(3) -0.002(2) 0.000(2) 0.003(2) C8 0.018(2) 0.029(2) 0.029(3) -0.002(2) 0.001(2) 0.006(2) C9 0.022(2) 0.034(3) 0.030(3) -0.002(2) 0.002(2) 0.006(2) C10 0.029(2) 0.027(3) 0.030(3) 0.004(2) -0.002(2) 0.009(2) C11 0.041(3) 0.048(3) 0.034(3) 0.006(2) 0.016(2) 0.005(2) C12 0.038(3) 0.063(4) 0.030(3) 0.014(3) 0.006(2) 0.002(3) C13 0.075(4) 0.047(3) 0.043(3) 0.010(3) 0.008(3) 0.004(3) C14 0.143(7) 0.076(4) 0.077(5) 0.062(5) 0.033(5) 0.018(4) C15 0.027(2) 0.034(3) 0.030(3) -0.006(2) 0.001(2) -0.001(2) C16 0.037(3) 0.038(3) 0.041(3) 0.000(2) 0.003(2) -0.007(2) C17 0.066(4) 0.054(3) 0.061(4) -0.023(3) 0.020(3) -0.022(3) C18 0.021(2) 0.027(3) 0.031(3) 0.000(2) -0.004(2) -0.003(2) C19 0.030(3) 0.034(3) 0.042(3) 0.002(2) -0.006(2) -0.005(2) C20 0.042(3) 0.043(3) 0.030(3) -0.002(3) 0.004(2) 0.004(2) C21 0.031(2) 0.034(3) 0.024(3) -0.008(2) 0.001(2) 0.000(2) C22 0.029(2) 0.050(3) 0.035(3) -0.010(2) -0.002(2) -0.004(2) C23 0.038(3) 0.040(3) 0.053(3) -0.001(2) 0.000(3) -0.016(2) #================================= # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 N 1.309(4) O2 C21 1.437(5) O2 C2 1.437(5) O3 C21 1.413(5) O3 C3 1.425(5) O4 C4 1.417(4) O5 C18 1.432(5) O5 C5 1.433(5) O6 C18 1.429(5) O6 C6 1.431(5) O7 C10 1.211(5) O8 C10 1.330(5) O8 C11 1.458(5) N C1 1.295(5) N C7 1.489(5) C1 C2 1.468(6) C2 C3 1.547(6) C3 C4 1.505(5) C4 C5 1.518(5) C5 C6 1.525(6) C7 C8 1.525(6) C7 C15 1.529(6) C8 C9 1.523(6) C9 C10 1.495(6) C11 C12 1.492(7) C12 C13 1.498(7) C13 C14 1.510(8) C15 C17 1.494(6) C15 C16 1.525(6) C18 C20 1.499(6) C18 C19 1.509(6) C21 C22 1.492(6) C21 C23 1.511(6) O4 H4o 0.88 C1 H1 0.95 C2 H2 0.95 C3 H3 0.95 C4 H4 0.95 C5 H5 0.95 C6 H6b 0.95 C6 H6a 0.95 C7 H7 0.95 C8 H8b 0.95 C8 H8a 0.95 C9 H9b 0.95 C9 H9a 0.95 C11 H11b 0.95 C11 H11a 0.95 C12 H12b 0.95 C12 H12a 0.95 C13 H13a 0.95 C13 H13b 0.95 C14 H14b 0.95 C14 H14a 0.95 C14 H14c 0.95 C15 H15 0.95 C16 H16b 0.95 C16 H16c 0.95 C16 H16a 0.95 C17 H17c 0.95 C17 H17b 0.95 C17 H17a 0.95 C19 H19b 0.95 C19 H19a 0.95 C19 H19c 0.95 C20 H20b 0.95 C20 H20c 0.95 C20 H20a 0.95 C22 H22c 0.95 C22 H22a 0.95 C22 H22b 0.95 C23 H23a 0.95 C23 H23c 0.95 C23 H23b 0.95 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 O2 C21 106.3(3) C3 O3 C21 108.8(3) C5 O5 C18 109.4(3) C6 O6 C18 105.7(3) C10 O8 C11 117.0(4) O1 N C1 120.9(3) C1 N C7 121.7(4) O1 N C7 117.4(3) N C1 C2 119.4(4) O2 C2 C1 106.8(3) O2 C2 C3 104.2(3) C1 C2 C3 118.2(3) O3 C3 C4 109.2(3) O3 C3 C2 103.9(3) C2 C3 C4 115.4(3) O4 C4 C3 111.7(3) O4 C4 C5 109.9(3) C3 C4 C5 112.1(3) O5 C5 C4 110.4(3) O5 C5 C6 102.8(3) C4 C5 C6 112.1(3) O6 C6 C5 102.6(3) N C7 C8 110.2(3) N C7 C15 108.0(3) C8 C7 C15 114.4(3) C7 C8 C9 113.5(4) C8 C9 C10 111.7(4) O7 C10 O8 124.0(4) O7 C10 C9 124.4(4) O8 C10 C9 111.6(4) O8 C11 C12 110.6(4) C11 C12 C13 114.9(5) C12 C13 C14 113.8(6) C16 C15 C17 111.0(4) C7 C15 C17 113.0(4) C7 C15 C16 110.9(4) O5 C18 O6 106.0(3) O6 C18 C20 111.2(4) O6 C18 C19 107.7(3) O5 C18 C20 109.3(3) O5 C18 C19 109.2(4) C19 C18 C20 113.2(4) O2 C21 O3 104.1(3) O3 C21 C22 109.4(4) O3 C21 C23 111.3(4) O2 C21 C22 107.3(4) O2 C21 C23 110.6(4) C22 C21 C23 113.6(4) C4 O4 H4o 108.4 N C1 H1 120.3 C2 C1 H1 120.3 O2 C2 H2 108.9 C1 C2 H2 109.1 C3 C2 H2 109.1 O3 C3 H3 109.4 C4 C3 H3 109.3 C2 C3 H3 109.4 O4 C4 H4 107.7 C3 C4 H4 107.5 C5 C4 H4 107.6 O5 C5 H5 110.5 C4 C5 H5 110.5 C6 C5 H5 110.4 H6a C6 H6b 109.6 O6 C6 H6b 111.2 C5 C6 H6b 111.2 O6 C6 H6a 111.0 C5 C6 H6a 111.0 N C7 H7 107.9 C8 C7 H7 108.1 C15 C7 H7 108.0 H8a C8 H8b 109.6 C9 C8 H8b 108.4 C7 C8 H8b 108.6 C9 C8 H8a 108.2 C7 C8 H8a 108.5 H9a C9 H9b 109.5 C10 C9 H9b 108.9 C8 C9 H9b 109.0 C10 C9 H9a 108.8 C8 C9 H9a 108.9 H11a C11 H11b 109.4 O8 C11 H11b 109.1 C12 C11 H11b 109.3 O8 C11 H11a 109.2 C12 C11 H11a 109.3 H12a C12 H12b 109.4 C11 C12 H12b 108.2 C13 C12 H12b 108.1 C11 C12 H12a 108.1 C13 C12 H12a 108.1 H13a C13 H13b 109.6 C12 C13 H13a 108.3 C14 C13 H13a 108.5 C12 C13 H13b 108.4 C14 C13 H13b 108.3 H14a C14 H14b 108.7 H14b C14 H14c 109.6 C13 C14 H14b 108.4 H14a C14 H14c 108.3 C13 C14 H14a 113.7 C13 C14 H14c 108.1 C17 C15 H15 107.5 C16 C15 H15 107.1 C7 C15 H15 107.1 H16b C16 H16c 109.5 H16a C16 H16b 109.1 C15 C16 H16b 109.1 H16a C16 H16c 109.1 C15 C16 H16c 109.1 C15 C16 H16a 110.9 H17b C17 H17c 109.7 H17a C17 H17c 108.6 C15 C17 H17c 108.8 H17a C17 H17b 108.4 C15 C17 H17b 108.5 C15 C17 H17a 112.8 H19a C19 H19b 109.6 H19b C19 H19c 109.5 C18 C19 H19b 109.5 H19a C19 H19c 109.5 C18 C19 H19a 109.2 C18 C19 H19c 109.6 H20b C20 H20c 109.6 H20a C20 H20b 109.4 C18 C20 H20b 109.7 H20a C20 H20c 109.3 C18 C20 H20c 109.6 C18 C20 H20a 109.2 H22a C22 H22c 110.2 H22b C22 H22c 109.3 C21 C22 H22c 110.1 H22a C22 H22b 109.9 C21 C22 H22a 107.4 C21 C22 H22b 110.0 H23a C23 H23c 109.4 H23a C23 H23b 109.2 C21 C23 H23a 110.7 H23b C23 H23c 109.1 C21 C23 H23c 109.3 C21 C23 H23b 109.0 loop_ _publ_manuscript_incl_extra_item '_geom_bond_atom_site_label_D' '_geom_bond_atom_site_label_H' '_geom_contact_atom_site_label_A' '_geom_bond_distance_DH' '_geom_contact_distance_HA' '_geom_contact_distance_DA' '_geom_angle_DHA' '_geom_contact_site_symmetry_A' loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A O4 H4o O1 0.88 1.90 2.692(5) 147.9(2) 1_655 #=================================== data_sine4a _database_code_depnum_ccdc_archive 'CCDC 236554' #=================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (S)-N-(3-buthoxycarbonyl-1-cyclohexylpropyl)-2,3-O- isopropylidene-5-deoxy-D-ribose-imine N-oxide ; _chemical_formula_sum 'C22 H39 N O6' _chemical_formula_moiety 'C22 H39 N O6' _chemical_formula_weight 413.54 #=================================== # 6. CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,-y,1/2+z -x,1/2+y,1/2-z 1/2+x,1/2-y,-z _cell_length_a 5.379(1) _cell_length_b 15.901(3) _cell_length_c 27.782(6) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 2376.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120 _cell_measurement_reflns_used 7630 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.34 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_process_details none #=================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'x-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation scans with narrow frames' _diffrn_standards_decay_% 0 _diffrn_reflns_number 53147 _diffrn_reflns_av_R_equivalents 0.110 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 27.34 _diffrn_reflns_reduction_process 53147 _reflns_number_total 5347 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_theta_full 27.34 _reflns_number_gt 3481 _reflns_threshold_expression I>3\s(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution ; SIR97 (Altomare et al., 1997 ), KRYSTAL ; _computing_structure_refinement 'modified ORFLS(1962), KRYSTAL' _computing_molecular_graphics ; ORTEP-III (Burnett & Johnson, 1996), KRYSTAL ; _computing_publication_material KRYSTAL _atom_type_scat_source IntTabIV #=================================== # 8. REFINEMENT DATA _refine_special_details ; ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w= 1/{[\s~cs~(F^2^)+B+(1+A)F^2^]^1/2^- |F|}^2^ where A = 0.05 and B = 0.05 ; _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3481 _refine_ls_number_parameters 290 _refine_ls_number_restraints 6 _refine_ls_number_constraints 23 _refine_ls_R_factor_gt 0.048 _refine_ls_wR_factor_ref 0.054 _refine_ls_goodness_of_fit_ref 1.247 _refine_ls_shift/su_max 0.089 _refine_ls_shift/su_mean 0.007 _refine_diff_density_max 0.23(5) _refine_diff_density_min -0.27(5) #========================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy O1 0.6719(3) 0.74182(10) 0.67585(6) 0.0723(10) Uij 1.00 O2 0.3362(3) 0.51453(10) 0.67823(6) 0.0722(10) Uij 1.00 O3 0.0473(3) 0.55241(9) 0.73314(6) 0.0619(9) Uij 1.00 O4 0.3780(4) 0.74516(11) 0.76300(6) 0.0813(11) Uij 1.00 O5 0.3589(4) 0.62462(12) 0.52802(7) 0.0851(12) Uij 1.00 O6 0.5750(4) 0.51672(12) 0.55655(8) 0.0958(14) Uij 1.00 N1 0.4899(3) 0.72028(11) 0.64762(6) 0.0573(10) Uij 1.00 C1 0.3484(4) 0.6564(1) 0.65591(8) 0.059(1) Uij 1.00 C2 0.4059(4) 0.5960(1) 0.69554(9) 0.061(1) Uij 1.00 C3 0.2545(4) 0.6058(1) 0.74185(8) 0.059(1) Uij 1.00 C4 0.1680(5) 0.6934(1) 0.75457(8) 0.063(1) Uij 1.00 C5 0.0122(6) 0.6931(2) 0.79952(10) 0.083(2) Uij 1.00 C6 0.4696(4) 0.7688(1) 0.60175(7) 0.057(1) Uij 1.00 C7 0.6884(5) 0.7430(2) 0.57030(9) 0.069(1) Uij 1.00 C8 0.7444(5) 0.6498(2) 0.56812(9) 0.068(1) Uij 1.00 C9 0.5391(5) 0.5984(2) 0.54861(8) 0.068(1) Uij 1.00 C10 0.1402(4) 0.4816(1) 0.70741(8) 0.060(1) Uij 1.00 C11 -0.0589(5) 0.4491(2) 0.67496(11) 0.084(2) Uij 1.00 C12 0.2417(7) 0.4156(2) 0.74029(11) 0.087(2) Uij 1.00 C13 0.4525(4) 0.8626(1) 0.61146(8) 0.059(1) Uij 1.00 C14 0.2457(5) 0.8845(2) 0.64670(9) 0.072(1) Uij 1.00 C15 0.2174(6) 0.9791(2) 0.65338(10) 0.089(2) Uij 1.00 C16 0.1785(7) 1.0230(2) 0.60597(11) 0.097(2) Uij 1.00 C17 0.3864(6) 1.0035(2) 0.57166(11) 0.096(2) Uij 1.00 C18 0.4138(5) 0.9097(2) 0.56419(9) 0.080(2) Uij 1.00 C19 0.3774(8) 0.4603(2) 0.54072(17) 0.129(3) Uij 1.00 C20a 0.414(2) 0.3785(4) 0.5682(4) 0.134(7) Uij 0.64(1) C20b 0.479(4) 0.3733(8) 0.5360(6) 0.139(12) Uij 0.36(1) C21a 0.629(2) 0.3329(5) 0.5520(3) 0.138(7) Uij 0.64(1) C21b 0.434(5) 0.3271(15) 0.5789(9) 0.261(26) Uij 0.36(1) C22a 0.648(4) 0.2476(5) 0.5746(7) 0.212(13) Uij 0.64(1) C22b 0.476(10) 0.2356(17) 0.5815(19) 0.370(53) Uij 0.36(1) H4o 0.476 0.7440 0.7350 0.090 Uiso 1.00 H1 0.205 0.6477 0.6365 0.070 Uiso 1.00 H2 0.579 0.5971 0.7027 0.073 Uiso 1.00 H3 0.348 0.5837 0.7680 0.070 Uiso 1.00 H4 0.074 0.7158 0.7287 0.076 Uiso 1.00 H5a -0.129 0.6585 0.7939 0.099 Uiso 1.00 H5b -0.040 0.7488 0.8068 0.099 Uiso 1.00 H5c 0.106 0.6714 0.8257 0.099 Uiso 1.00 H6 0.321 0.7519 0.5860 0.068 Uiso 1.00 H7a 0.832 0.7707 0.5822 0.083 Uiso 1.00 H7b 0.655 0.7617 0.5385 0.083 Uiso 1.00 H8a 0.780 0.6308 0.5998 0.082 Uiso 1.00 H8b 0.886 0.6418 0.5483 0.082 Uiso 1.00 H11a -0.189 0.4273 0.6943 0.101 Uiso 1.00 H11b 0.006 0.4059 0.6550 0.101 Uiso 1.00 H11c -0.121 0.4936 0.6555 0.101 Uiso 1.00 H12a 0.111 0.3937 0.7597 0.104 Uiso 1.00 H12b 0.366 0.4396 0.7604 0.104 Uiso 1.00 H12c 0.312 0.3715 0.7217 0.104 Uiso 1.00 H13 0.606 0.8805 0.6250 0.071 Uiso 1.00 H14a 0.283 0.8597 0.6770 0.086 Uiso 1.00 H14b 0.094 0.8624 0.6348 0.086 Uiso 1.00 H15a 0.364 1.0006 0.6681 0.107 Uiso 1.00 H15b 0.078 0.9896 0.6736 0.107 Uiso 1.00 H16a 0.172 1.0820 0.6113 0.117 Uiso 1.00 H16b 0.026 1.0047 0.5923 0.117 Uiso 1.00 H17a 0.537 1.0252 0.5843 0.115 Uiso 1.00 H17b 0.352 1.0294 0.5416 0.115 Uiso 1.00 H18a 0.268 0.8890 0.5491 0.096 Uiso 1.00 H18b 0.553 0.8998 0.5439 0.096 Uiso 1.00 H19aa 0.389 0.4507 0.5071 0.155 Uiso 0.64(1) H19ab 0.219 0.4838 0.5480 0.155 Uiso 0.64(1) H19ba 0.315 0.4786 0.5105 0.155 Uiso 0.36(1) H19bb 0.247 0.4606 0.5637 0.155 Uiso 0.36(1) H20aa 0.271 0.3441 0.5638 0.160 Uiso 0.64(1) H20ab 0.434 0.3910 0.6014 0.160 Uiso 0.64(1) H20ba 0.653 0.3762 0.5304 0.166 Uiso 0.36(1) H20bb 0.401 0.3458 0.5097 0.166 Uiso 0.36(1) H21aa 0.773 0.3642 0.5600 0.166 Uiso 0.64(1) H21ab 0.619 0.3266 0.5180 0.166 Uiso 0.64(1) H21ba 0.264 0.3359 0.5866 0.311 Uiso 0.36(1) H21bb 0.536 0.3519 0.6030 0.311 Uiso 0.36(1) H22aa 0.790 0.2174 0.5637 0.253 Uiso 0.64(1) H22ab 0.503 0.2163 0.5664 0.253 Uiso 0.64(1) H22ac 0.658 0.2539 0.6084 0.253 Uiso 0.64(1) H22ba 0.446 0.2049 0.6107 0.449 Uiso 0.36(1) H22bb 0.646 0.2270 0.5743 0.449 Uiso 0.36(1) H22bc 0.374 0.2110 0.5579 0.449 Uiso 0.36(1) loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0657(9) 0.0752(10) 0.0759(10) -0.0178(9) -0.0200(9) 0.0101(8) O2 0.0776(10) 0.0529(8) 0.0861(11) -0.0082(8) 0.0193(9) -0.0091(8) O3 0.0635(9) 0.0460(8) 0.0763(10) -0.0009(7) 0.0081(8) -0.0017(7) O4 0.0993(13) 0.0680(10) 0.0767(10) -0.0225(10) -0.0033(10) -0.0102(9) O5 0.0840(12) 0.0875(12) 0.0837(12) 0.0086(11) -0.0211(11) -0.0061(10) O6 0.1027(14) 0.0714(12) 0.1133(15) 0.0067(11) -0.0179(13) 0.0003(11) N1 0.0534(10) 0.0594(10) 0.0590(10) -0.0069(9) -0.0027(9) 0.0034(8) C1 0.055(1) 0.056(1) 0.065(1) -0.006(1) -0.002(1) -0.001(1) C2 0.058(1) 0.049(1) 0.074(1) -0.003(1) -0.001(1) 0.002(1) C3 0.064(1) 0.050(1) 0.062(1) -0.002(1) -0.005(1) 0.004(1) C4 0.078(1) 0.048(1) 0.064(1) -0.002(1) -0.002(1) 0.000(1) C5 0.108(2) 0.061(1) 0.079(2) 0.002(2) 0.015(2) -0.005(1) C6 0.055(1) 0.064(1) 0.050(1) -0.002(1) -0.002(1) 0.004(1) C7 0.063(1) 0.075(2) 0.070(1) 0.000(1) 0.007(1) -0.002(1) C8 0.060(1) 0.078(2) 0.068(1) 0.007(1) 0.000(1) -0.005(1) C9 0.070(2) 0.073(2) 0.061(1) 0.010(1) 0.002(1) -0.003(1) C10 0.059(1) 0.045(1) 0.074(1) 0.003(1) 0.004(1) 0.001(1) C11 0.073(2) 0.070(2) 0.110(2) 0.001(1) -0.006(2) -0.020(2) C12 0.119(2) 0.055(1) 0.087(2) 0.017(1) -0.006(2) 0.006(1) C13 0.060(1) 0.058(1) 0.058(1) -0.004(1) 0.000(1) 0.004(1) C14 0.083(2) 0.069(1) 0.063(1) 0.000(1) 0.012(1) -0.002(1) C15 0.124(2) 0.067(2) 0.077(2) 0.012(2) 0.024(2) -0.002(1) C16 0.117(2) 0.081(2) 0.093(2) 0.032(2) 0.016(2) 0.012(2) C17 0.122(3) 0.078(2) 0.087(2) 0.027(2) 0.021(2) 0.027(1) C18 0.096(2) 0.081(2) 0.062(1) 0.016(1) 0.016(1) 0.014(1) C19 0.132(3) 0.073(2) 0.183(4) -0.015(2) -0.037(3) -0.008(2) C20a 0.178(8) 0.082(5) 0.141(8) -0.024(5) 0.028(6) -0.022(5) C20b 0.183(15) 0.107(10) 0.126(11) 0.024(11) 0.006(11) 0.004(9) C21a 0.146(7) 0.103(5) 0.167(8) 0.012(5) -0.001(6) 0.005(5) C21b 0.250(25) 0.166(18) 0.368(33) 0.080(18) 0.125(24) 0.152(20) C22a 0.290(18) 0.081(5) 0.264(14) 0.027(8) -0.083(13) 0.018(7) C22b 0.477(71) 0.241(32) 0.391(47) -0.109(38) -0.036(49) 0.161(32) #================================= # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 N1 1.301(2) O2 C10 1.429(3) O2 C2 1.431(3) O3 C3 1.421(3) O3 C10 1.424(3) O4 C4 1.417(3) O5 C9 1.200(3) O6 C9 1.331(3) O6 C19 1.458(4) N1 C1 1.289(3) N1 C6 1.493(3) C1 C2 1.494(3) C2 C3 1.531(4) C3 C4 1.511(3) C4 C5 1.504(4) C6 C13 1.519(3) C6 C7 1.522(3) C7 C8 1.514(4) C8 C9 1.477(4) C10 C11 1.492(3) C10 C12 1.495(4) C13 C14 1.522(3) C13 C18 1.526(3) C14 C15 1.523(4) C15 C16 1.505(4) C16 C17 1.501(4) C17 C18 1.513(4) C19 C20b 1.494(13) C19 C20a 1.522(10) C20a C20b 0.964(14) C20a C21b 0.876(17) C20a C21a 1.434(11) C20b C21a 1.123(15) C20b C21b 1.421(17) C21a C21b 1.289(23) C21a C22a 1.499(12) C21b C22b 1.473(18) C21b C22a 1.714(28) C22a C22b 0.97(5) O4 H4o 0.94 C1 H1 0.95 C2 H2 0.95 C3 H3 0.95 C4 H4 0.95 C5 H5a 0.95 C5 H5b 0.95 C5 H5c 0.95 C6 H6 0.95 C7 H7b 0.95 C7 H7a 0.95 C8 H8b 0.95 C8 H8a 0.95 C11 H11b 0.95 C11 H11a 0.95 C11 H11c 0.95 C12 H12b 0.95 C12 H12a 0.95 C12 H12c 0.95 C13 H13 0.95 C14 H14a 0.95 C14 H14b 0.95 C15 H15b 0.95 C15 H15a 0.95 C16 H16b 0.95 C16 H16a 0.95 C17 H17a 0.95 C17 H17b 0.95 C18 H18a 0.95 C18 H18b 0.95 C19 H19bb 0.95 C19 H19aa 0.95 C19 H19ab 0.95 C19 H19ba 0.95 C20a H20ab 0.95 C20a H20aa 0.95 C20b H20bb 0.95 C20b H20ba 0.95 C21a H21ab 0.95 C21a H21aa 0.95 C21b H21ba 0.95 C21b H21bb 0.95 C22a H22ab 0.95 C22a H22ac 0.95 C22a H22aa 0.95 C22b H22ba 0.96 C22b H22bb 0.95 C22b H22bc 0.95 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 O2 C10 109.5(2) C3 O3 C10 106.4(2) C9 O6 C19 116.4(2) O1 N1 C1 123.0(2) C1 N1 C6 121.1(2) O1 N1 C6 115.7(2) N1 C1 C2 121.1(2) O2 C2 C1 106.3(2) O2 C2 C3 103.6(2) C1 C2 C3 116.3(2) O3 C3 C4 110.4(2) O3 C3 C2 102.3(2) C2 C3 C4 117.0(2) O4 C4 C5 108.0(2) O4 C4 C3 109.2(2) C3 C4 C5 111.3(2) N1 C6 C13 111.1(2) N1 C6 C7 107.1(2) C7 C6 C13 114.4(2) C6 C7 C8 116.1(2) C7 C8 C9 114.1(2) O5 C9 O6 122.4(3) O5 C9 C8 125.9(2) O6 C9 C8 111.8(2) O2 C10 O3 104.7(2) O3 C10 C11 109.0(2) O3 C10 C12 112.1(2) O2 C10 C11 108.3(2) O2 C10 C12 109.5(2) C11 C10 C12 112.9(2) C6 C13 C14 112.5(2) C6 C13 C18 109.7(2) C14 C13 C18 110.0(2) C13 C14 C15 112.2(2) C14 C15 C16 111.4(2) C15 C16 C17 110.9(3) C16 C17 C18 111.3(2) C13 C18 C17 112.3(2) O6 C19 C20b 109.3(8) C20a C19 C20b 37.3(6) O6 C19 C20a 106.2(4) C19 C20a C21a 112.3(8) C19 C20b C21b 110.1(16) C20a C21a C22a 112.4(11) C20b C21b C22b 121.7(28) C4 O4 H4o 107.4 N1 C1 H1 119.5 C2 C1 H1 119.5 O2 C2 H2 110.1 C1 C2 H2 110.1 C3 C2 H2 110.1 O3 C3 H3 108.9 C4 C3 H3 108.9 C2 C3 H3 108.9 O4 C4 H4 109.5 C5 C4 H4 109.4 C3 C4 H4 109.5 H5a C5 H5b 109.8 H5a C5 H5c 109.8 C4 C5 H5a 108.0 H5b C5 H5c 109.5 C4 C5 H5b 109.8 C4 C5 H5c 109.8 N1 C6 H6 108.0 C13 C6 H6 108.0 C7 C6 H6 108.0 H7a C7 H7b 109.5 C8 C7 H7b 107.8 C6 C7 H7b 107.8 C8 C7 H7a 107.8 C6 C7 H7a 107.8 H8a C8 H8b 109.5 C9 C8 H8b 108.3 C7 C8 H8b 108.3 C9 C8 H8a 108.3 C7 C8 H8a 108.3 H11a C11 H11b 109.8 H11b C11 H11c 109.5 C10 C11 H11b 109.8 H11a C11 H11c 109.8 C10 C11 H11a 108.3 C10 C11 H11c 109.8 H12a C12 H12b 109.5 H12b C12 H12c 109.5 C10 C12 H12b 109.5 H12a C12 H12c 109.4 C10 C12 H12a 109.5 C10 C12 H12c 109.5 C6 C13 H13 108.2 C14 C13 H13 108.2 C18 C13 H13 108.2 H14a C14 H14b 109.5 C15 C14 H14a 108.8 C13 C14 H14a 108.8 C15 C14 H14b 108.8 C13 C14 H14b 108.8 H15a C15 H15b 109.5 C16 C15 H15b 109.0 C14 C15 H15b 109.0 C16 C15 H15a 109.0 C14 C15 H15a 109.0 H16a C16 H16b 109.5 C17 C16 H16b 109.1 C15 C16 H16b 109.1 C17 C16 H16a 109.1 C15 C16 H16a 109.1 H17a C17 H17b 109.5 C16 C17 H17a 109.0 C18 C17 H17a 109.0 C16 C17 H17b 109.0 C18 C17 H17b 109.0 H18a C18 H18b 109.5 C17 C18 H18a 108.8 C13 C18 H18a 108.8 C17 C18 H18b 108.8 C13 C18 H18b 108.8 H19ba C19 H19bb 109.5 C20b C19 H19bb 109.5 O6 C19 H19bb 109.5 H19aa C19 H19ab 109.5 O6 C19 H19aa 110.3 C20a C19 H19aa 110.3 O6 C19 H19ab 110.3 C20a C19 H19ab 110.3 C20b C19 H19ba 109.5 O6 C19 H19ba 109.5 H20aa C20a H20ab 109.5 C21a C20a H20ab 108.8 C19 C20a H20ab 108.8 C21a C20a H20aa 108.7 C19 C20a H20aa 108.7 H20ba C20b H20bb 109.4 C21b C20b H20bb 109.5 C19 C20b H20bb 109.4 C21b C20b H20ba 109.2 C19 C20b H20ba 109.2 H21aa C21a H21ab 109.4 C20a C21a H21ab 108.7 C22a C21a H21ab 108.9 C20a C21a H21aa 108.7 C22a C21a H21aa 108.6 C20b C21b H21ba 106.0 C22b C21b H21ba 106.3 H21ba C21b H21bb 109.5 C20b C21b H21bb 106.3 C22b C21b H21bb 106.8 H22ab C22a H22ac 109.5 H22aa C22a H22ab 108.5 C21a C22a H22ab 108.5 H22aa C22a H22ac 109.1 C21a C22a H22ac 108.8 C21a C22a H22aa 112.4 H22bb C22b H22ba 105 H22bb C22b H22bc 111 C21b C22b H22bc 107 H22ba C22b H22bb 105 C21b C22b H22ba 121 C21b C22b H22bb 106.1 #loop_ #_publ_manuscript_incl_extra_item #'_geom_bond_atom_site_label_D' #'_geom_bond_atom_site_label_H' #'_geom_contact_atom_site_label_A' #'_geom_bond_distance_DH' #'_geom_contact_distance_HA' #'_geom_contact_distance_DA' #'_geom_angle_DHA' loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA O4 H4o O1 0.940(2) 1.952(2) 2.892(2) 178.6(1)