# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 #============================================================================== _audit_creation_date 2004-05-27 _audit_creation_method 'by teXsan for Windows v1.06' _audit_update_record ; 2004-07-15 refined ; _publ_requested_category FO _publ_contact_author_name "Shin'ichi Nakatsuji" _publ_contact_author_address ; Material Science University of Hyogo 3-2-1 Kouto Kamigori Japan/Hyogo 678-1297 JAPAN ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' +81-791-58-0163 ' _publ_contact_author_fax ' +81-791-58-0164 ' _publ_contact_author_email nakatuji@sci.u-hyogo.ac.jp _publ_section_title ; Azobenzene Derivatives with Long Alkyl Chain and Aminoxyls ; _publ_section_references ; Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. Molecular Structure Corporation. (1997-1999). teXsan for Windows. Single Crystal Structure Analysis Software. Version 1.06. MSC, 9009 New Trails Drive, The Woodlands, TX 77381, USA. Sheldrick, G.M. (1997). ; loop_ _publ_author_name S.Nakatsuji 'Hiroki Akutsu' 'Takamitsu Amano' 'Masahiro Fujino' 'Jun-ichi Yamada' #============================================================================== data_3b _database_code_depnum_ccdc_archive 'CCDC 240929' _audit_creation_date 2004-05-27 _audit_creation_method 'by teXsan for Windows v1.06' _audit_update_record ; ? ; #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows v1.06 (MSC, 1997-99)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan for Windows v1.06 (MSC, 1997-99)' _computing_publication_material 'teXsan for Windows v1.06 (MSC, 1997-99)' #------------------------------------------------------------------------------ _cell_length_a 5.973(6) _cell_length_b 42.691(9) _cell_length_c 12.856(7) _cell_angle_alpha 90 _cell_angle_beta 100.52(7) _cell_angle_gamma 90 _cell_volume 3223(3) _cell_formula_units_Z 4 _cell_measurement_temperature 303.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.7 _cell_measurement_theta_max 14.0 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' 1/2-x,1/2+y,1/2-z ' -x, -y, -z' 1/2+x,1/2-y,1/2+z #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.135 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 550.76 _chemical_formula_analytical ? _chemical_formula_sum 'C33 H48 N3 O4 ' _chemical_formula_moiety 'C33 H48 N3 O4 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1196.00 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North,Phillips & Matthews, 1968)' _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.951 _exptl_special_details ; The scan width was (0.73+0.30tan\q)\% with an \w scan speed of 16\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 303.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.37 _diffrn_reflns_number 6455 _reflns_number_total 6205 _reflns_number_gt 994 _reflns_threshold_expression I>3.00\s(I) _diffrn_reflns_av_R_equivalents 0.10032 _diffrn_reflns_av_sigmaI/netI 0.372 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 50 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 27.52 _diffrn_measured_fraction_theta_max 0.821 _diffrn_reflns_theta_full 24.907 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.10997 _diffrn_orient_matrix_UB_12 0.01786 _diffrn_orient_matrix_UB_13 0.01225 _diffrn_orient_matrix_UB_21 0.09950 _diffrn_orient_matrix_UB_22 -0.01230 _diffrn_orient_matrix_UB_23 0.05656 _diffrn_orient_matrix_UB_31 0.08371 _diffrn_orient_matrix_UB_32 -0.00884 _diffrn_orient_matrix_UB_33 -0.05395 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 132 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 192 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 16 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 12 0.004 0.003 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #============================================================================== # 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_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 1.745(1) -0.0332(2) 1.4519(6) 0.070(3) 1.000 . Uani d ? O(2) 0.014(1) 0.1366(2) 0.6869(6) 0.081(3) 1.000 . Uani d ? O(3) -0.299(1) 0.1127(2) 0.6042(7) 0.113(4) 1.000 . Uani d ? O(4) -0.775(1) 0.2379(2) 0.5309(6) 0.104(3) 1.000 . Uani d ? N(1) 2.408(2) -0.1125(3) 1.770(1) 0.096(5) 1.000 . Uani d ? N(2) 2.226(2) -0.1214(3) 1.7333(9) 0.090(5) 1.000 . Uani d ? N(3) -0.638(1) 0.2153(2) 0.5518(8) 0.066(4) 1.000 . Uani d ? C(1) 2.745(4) -0.1815(4) 1.976(1) 0.128(9) 1.000 . Uani d ? C(2) 2.861(2) -0.1562(5) 1.954(1) 0.117(7) 1.000 . Uani d ? C(3) 2.524(4) -0.1880(4) 1.930(2) 0.136(9) 1.000 . Uani d ? C(4) 2.745(3) -0.1347(4) 1.886(2) 0.114(7) 1.000 . Uani d ? C(5) 2.419(3) -0.1655(5) 1.861(1) 0.106(7) 1.000 . Uani d ? C(6) 2.525(4) -0.1384(4) 1.841(1) 0.098(8) 1.000 . Uani d ? C(7) 2.116(3) -0.0953(3) 1.664(1) 0.075(6) 1.000 . Uani d ? C(8) 2.205(2) -0.0673(3) 1.641(1) 0.071(5) 1.000 . Uani d ? C(9) 1.900(3) -0.1024(3) 1.617(1) 0.090(6) 1.000 . Uani d ? C(10) 2.073(2) -0.0467(2) 1.5702(9) 0.062(5) 1.000 . Uani d ? C(11) 1.761(2) -0.0824(3) 1.545(1) 0.075(5) 1.000 . Uani d ? C(12) 1.853(2) -0.0549(3) 1.523(1) 0.065(5) 1.000 . Uani d ? C(13) 1.524(2) -0.0409(3) 1.4015(8) 0.072(5) 1.000 . Uani d ? C(14) 1.459(2) -0.0110(2) 1.3324(9) 0.070(4) 1.000 . Uani d ? C(15) 1.211(2) -0.0125(2) 1.2653(9) 0.066(4) 1.000 . Uani d ? C(16) 1.151(2) 0.0166(3) 1.1986(9) 0.084(5) 1.000 . Uani d ? C(17) 0.917(2) 0.0180(3) 1.1343(9) 0.070(4) 1.000 . Uani d ? C(18) 0.865(2) 0.0468(3) 1.069(1) 0.084(5) 1.000 . Uani d ? C(19) 0.634(2) 0.0490(3) 1.0073(9) 0.079(5) 1.000 . Uani d ? C(20) 0.581(2) 0.0782(3) 0.942(1) 0.087(5) 1.000 . Uani d ? C(21) 0.357(2) 0.0797(2) 0.8746(9) 0.090(5) 1.000 . Uani d ? C(22) 0.291(2) 0.1091(3) 0.8087(9) 0.082(5) 1.000 . Uani d ? C(23) 0.080(2) 0.1071(3) 0.732(1) 0.110(6) 1.000 . Uani d ? C(24) -0.189(2) 0.1360(3) 0.6270(9) 0.065(5) 1.000 . Uani d ? C(25) -0.276(2) 0.1690(2) 0.5921(9) 0.049(4) 1.000 . Uani d ? C(26) -0.385(2) 0.1818(3) 0.6818(8) 0.066(4) 1.000 . Uani d ? C(27) -0.462(2) 0.1678(2) 0.4929(8) 0.059(4) 1.000 . Uani d ? C(28) -0.497(2) 0.2138(3) 0.6575(9) 0.065(5) 1.000 . Uani d ? C(29) -0.571(2) 0.1992(3) 0.462(1) 0.057(4) 1.000 . Uani d ? C(30) -0.313(2) 0.2394(2) 0.6686(8) 0.084(5) 1.000 . Uani d ? C(31) -0.644(2) 0.2212(3) 0.7383(9) 0.103(5) 1.000 . Uani d ? C(32) -0.784(2) 0.1928(2) 0.3788(8) 0.076(4) 1.000 . Uani d ? C(33) -0.414(2) 0.2186(2) 0.4107(8) 0.072(4) 1.000 . Uani d ? H(1) 2.8204 -0.2010 2.0148 0.051 1.000 . Uiso c ? H(2) 3.0335 -0.1516 1.9989 0.051 1.000 . Uiso c ? H(3) 2.4206 -0.2045 1.9411 0.051 1.000 . Uiso c ? H(4) 2.8307 -0.1134 1.8780 0.051 1.000 . Uiso c ? H(5) 2.2499 -0.1666 1.8190 0.051 1.000 . Uiso c ? H(6) 2.3469 -0.0542 1.6602 0.051 1.000 . Uiso c ? H(7) 1.8415 -0.1241 1.6390 0.051 1.000 . Uiso c ? H(8) 2.1048 -0.0249 1.5482 0.051 1.000 . Uiso c ? H(9) 1.6000 -0.0906 1.5132 0.051 1.000 . Uiso c ? H(10) 1.4907 -0.0444 1.3185 0.051 1.000 . Uiso c ? H(11) 1.3693 -0.0342 1.4098 0.051 1.000 . Uiso c ? H(12) 1.3834 0.0076 1.3629 0.051 1.000 . Uiso c ? H(13) 1.4835 -0.0051 1.2680 0.051 1.000 . Uiso c ? H(14) 1.1652 -0.0278 1.2141 0.051 1.000 . Uiso c ? H(15) 1.0714 -0.0104 1.3029 0.051 1.000 . Uiso c ? H(16) 1.1647 0.0374 1.2337 0.051 1.000 . Uiso c ? H(17) 1.2508 0.0196 1.1434 0.051 1.000 . Uiso c ? H(18) 0.8760 -0.0016 1.0822 0.051 1.000 . Uiso c ? H(19) 0.7885 0.0132 1.1773 0.051 1.000 . Uiso c ? H(20) 0.8989 0.0646 1.1255 0.051 1.000 . Uiso c ? H(21) 0.9923 0.0499 1.0316 0.051 1.000 . Uiso c ? H(22) 0.6182 0.0304 0.9606 0.051 1.000 . Uiso c ? H(23) 0.5260 0.0461 1.0532 0.051 1.000 . Uiso c ? H(24) 0.6149 0.0964 0.9918 0.051 1.000 . Uiso c ? H(25) 0.7082 0.0809 0.8994 0.051 1.000 . Uiso c ? H(26) 0.3356 0.0613 0.8293 0.051 1.000 . Uiso c ? H(27) 0.2425 0.0770 0.9215 0.051 1.000 . Uiso c ? H(28) 0.3053 0.1277 0.8563 0.051 1.000 . Uiso c ? H(29) 0.4335 0.1137 0.7725 0.051 1.000 . Uiso c ? H(30) -0.0107 0.0961 0.7818 0.051 1.000 . Uiso c ? H(31) 0.1162 0.0889 0.6895 0.051 1.000 . Uiso c ? H(32) -0.1597 0.1834 0.5709 0.051 1.000 . Uiso c ? H(33) -0.5145 0.1685 0.6913 0.051 1.000 . Uiso c ? H(34) -0.2766 0.1798 0.7482 0.051 1.000 . Uiso c ? H(35) -0.3932 0.1547 0.4326 0.051 1.000 . Uiso c ? H(36) -0.5753 0.1510 0.5037 0.051 1.000 . Uiso c ? H(37) -0.2547 0.2491 0.7434 0.051 1.000 . Uiso c ? H(38) -0.1714 0.2355 0.6454 0.051 1.000 . Uiso c ? H(39) -0.3708 0.2593 0.6307 0.051 1.000 . Uiso c ? H(40) -0.5859 0.2205 0.8140 0.051 1.000 . Uiso c ? H(41) -0.7137 0.2431 0.7289 0.051 1.000 . Uiso c ? H(42) -0.7749 0.2077 0.7252 0.051 1.000 . Uiso c ? H(43) -0.9185 0.1920 0.4170 0.051 1.000 . Uiso c ? H(44) -0.8290 0.2107 0.3296 0.051 1.000 . Uiso c ? H(45) -0.8089 0.1745 0.3332 0.051 1.000 . Uiso c ? H(46) -0.3102 0.2319 0.4606 0.051 1.000 . Uiso c ? H(47) -0.2916 0.2087 0.3696 0.051 1.000 . Uiso c ? H(48) -0.4838 0.2337 0.3552 0.051 1.000 . Uiso c ? 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 O(1) 0.067(6) 0.058(6) 0.080(6) -0.005(5) 0.004(5) 0.019(5) O(2) 0.066(6) 0.053(6) 0.107(7) 0.004(5) -0.028(5) 0.010(5) O(3) 0.114(7) 0.047(6) 0.155(9) 0.006(5) -0.034(6) 0.007(6) O(4) 0.101(7) 0.081(6) 0.119(8) 0.059(5) -0.005(5) -0.013(5) N(1) 0.11(1) 0.072(9) 0.11(1) -0.017(9) 0.032(9) -0.030(8) N(2) 0.10(1) 0.08(1) 0.082(9) -0.012(8) -0.003(8) -0.031(7) N(3) 0.066(8) 0.050(7) 0.077(9) 0.009(6) 0.002(7) -0.019(6) C(1) 0.24(3) 0.05(1) 0.12(2) 0.03(1) 0.10(2) 0.05(1) C(2) 0.10(1) 0.17(2) 0.07(1) 0.08(1) -0.007(9) 0.02(1) C(3) 0.13(2) 0.12(2) 0.18(2) -0.05(1) 0.09(2) -0.05(2) C(4) 0.07(1) 0.10(1) 0.17(2) -0.02(1) 0.02(1) -0.02(1) C(5) 0.13(2) 0.09(1) 0.09(1) 0.06(1) -0.01(1) 0.01(1) C(6) 0.17(2) 0.07(1) 0.08(1) 0.06(2) 0.09(1) 0.04(1) C(7) 0.08(1) 0.05(1) 0.09(1) -0.01(1) 0.017(9) -0.01(1) C(8) 0.057(9) 0.062(9) 0.10(1) -0.026(8) 0.024(8) -0.025(9) C(9) 0.13(1) 0.051(9) 0.09(1) -0.02(1) 0.03(1) 0.002(8) C(10) 0.08(1) 0.034(8) 0.08(1) 0.002(8) 0.017(8) 0.014(7) C(11) 0.062(9) 0.06(1) 0.09(1) -0.035(9) -0.009(8) -0.002(9) C(12) 0.06(1) 0.07(1) 0.07(1) -0.020(9) 0.006(8) -0.014(8) C(13) 0.029(7) 0.12(1) 0.055(9) 0.001(7) -0.014(6) 0.028(8) C(14) 0.080(9) 0.058(8) 0.069(9) 0.015(7) 0.010(7) 0.009(7) C(15) 0.053(8) 0.072(9) 0.065(9) -0.004(7) -0.007(7) -0.019(7) C(16) 0.10(1) 0.061(9) 0.10(1) 0.018(8) 0.024(9) 0.040(8) C(17) 0.074(9) 0.069(9) 0.068(9) 0.005(8) 0.013(7) 0.007(7) C(18) 0.09(1) 0.08(1) 0.07(1) -0.014(9) 0.006(8) 0.003(8) C(19) 0.10(1) 0.08(1) 0.06(1) -0.023(8) 0.019(8) 0.013(8) C(20) 0.082(9) 0.09(1) 0.09(1) -0.008(9) 0.019(8) 0.006(9) C(21) 0.13(1) 0.059(9) 0.08(1) 0.018(8) 0.013(9) 0.032(8) C(22) 0.11(1) 0.064(9) 0.08(1) 0.014(8) 0.016(9) 0.011(8) C(23) 0.11(1) 0.08(1) 0.13(1) 0.022(9) -0.02(1) 0.04(1) C(24) 0.07(1) 0.06(1) 0.056(9) -0.010(9) -0.002(8) 0.005(9) C(25) 0.055(8) 0.047(8) 0.047(9) 0.014(6) 0.012(7) 0.018(7) C(26) 0.068(8) 0.060(8) 0.067(9) 0.004(7) 0.005(7) 0.020(7) C(27) 0.061(8) 0.030(7) 0.08(1) 0.017(6) 0.007(7) -0.003(6) C(28) 0.06(1) 0.08(1) 0.05(1) -0.022(8) 0.002(8) -0.016(8) C(29) 0.050(9) 0.055(8) 0.06(1) 0.001(7) 0.000(8) 0.013(7) C(30) 0.075(9) 0.076(9) 0.09(1) 0.010(7) -0.005(7) -0.024(7) C(31) 0.13(1) 0.11(1) 0.067(9) 0.024(9) 0.019(9) -0.009(8) C(32) 0.086(9) 0.090(9) 0.040(8) 0.016(7) -0.019(7) -0.012(6) C(33) 0.067(8) 0.088(8) 0.060(8) -0.008(7) 0.009(7) 0.020(7) #============================================================================== # REFINEMENT DATA _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00021|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 994 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0610 _refine_ls_wR_factor_all 0.0560 _refine_ls_wR_factor_ref 0.0560 _refine_ls_goodness_of_fit_all 1.957 _refine_ls_goodness_of_fit_ref 1.960 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0000 _refine_diff_density_min -0.20 _refine_diff_density_max 0.17 #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.38(2) . . ? O1 C13 1.40(1) . . ? O2 C23 1.41(2) . . ? O2 C24 1.31(1) . . ? O3 C24 1.20(1) . . ? O4 N3 1.26(1) . . ? N1 N2 1.16(1) . . ? N1 C6 1.53(2) . . ? N2 C7 1.50(2) . . ? N3 C28 1.46(2) . . ? N3 C29 1.46(2) . . ? C1 C2 1.34(2) . . ? C1 C3 1.38(3) . . ? C1 H1 1.03 . . no C2 C4 1.37(2) . . ? C2 H2 1.10 . . no C3 C5 1.38(3) . . ? C3 H3 0.96 . . no C4 C6 1.34(2) . . ? C4 H4 1.05 . . no C5 C6 1.37(2) . . ? C5 H5 1.06 . . no C7 C8 1.37(2) . . ? C7 C9 1.36(2) . . ? C8 C10 1.40(2) . . ? C8 H6 1.01 . . no C9 C11 1.41(2) . . ? C9 H7 1.05 . . no C10 C12 1.39(2) . . ? C10 H8 1.00 . . no C11 C12 1.35(2) . . ? C11 H9 1.04 . . no C13 C14 1.56(2) . . ? C13 H10 1.06 . . no C13 H11 0.99 . . no C14 C15 1.58(2) . . ? C14 H12 1.03 . . no C14 H13 0.90 . . no C15 C16 1.52(2) . . ? C15 H14 0.93 . . no C15 H15 1.04 . . no C16 C17 1.49(2) . . ? C16 H16 0.99 . . no C16 H17 1.02 . . no C17 C18 1.49(2) . . ? C17 H18 1.07 . . no C17 H19 1.04 . . no C18 C19 1.46(2) . . ? C18 H20 1.05 . . no C18 H21 0.98 . . no C19 C20 1.51(2) . . ? C19 H22 0.99 . . no C19 H23 0.96 . . no C20 C21 1.46(2) . . ? C20 H24 1.00 . . no C20 H25 1.02 . . no C21 C22 1.53(2) . . ? C21 H26 0.97 . . no C21 H27 0.99 . . no C22 C23 1.45(2) . . ? C22 H28 1.00 . . no C22 H29 1.06 . . no C23 H30 1.02 . . no C23 H31 1.00 . . no C24 C25 1.54(2) . . ? C25 C26 1.53(2) . . ? C25 C27 1.53(2) . . ? C25 H32 1.00 . . no C26 C28 1.53(2) . . ? C26 H33 0.98 . . no C26 H34 0.98 . . no C27 C29 1.51(2) . . ? C27 H35 1.09 . . no C27 H36 1.01 . . no C28 C30 1.54(2) . . ? C28 C31 1.51(2) . . ? C29 C32 1.53(2) . . ? C29 C33 1.49(2) . . ? C30 H37 1.05 . . no C30 H38 0.96 . . no C30 H39 1.01 . . no C31 H40 0.97 . . no C31 H41 1.02 . . no C31 H42 0.96 . . no C32 H43 1.01 . . no C32 H44 1.00 . . no C32 H45 0.97 . . no C33 H46 0.99 . . no C33 H47 1.06 . . no C33 H48 0.99 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O1 C13 116(1) . . . ? C23 O2 C24 113(1) . . . ? N2 N1 C6 107(2) . . . ? N1 N2 C7 106(2) . . . ? O4 N3 C28 118(1) . . . ? O4 N3 C29 117(1) . . . ? C28 N3 C29 121(1) . . . ? C2 C1 C3 124(3) . . . ? C2 C1 H1 123.9 . . . no C3 C1 H1 110.2 . . . no C1 C2 C4 117(3) . . . ? C1 C2 H2 120.1 . . . no C4 C2 H2 122.1 . . . no C1 C3 C5 115(3) . . . ? C1 C3 H3 132.6 . . . no C5 C3 H3 112.1 . . . no C2 C4 C6 122(2) . . . ? C2 C4 H4 116.2 . . . no C6 C4 H4 121.0 . . . no C3 C5 C6 123(2) . . . ? C3 C5 H5 125.5 . . . no C6 C5 H5 112.0 . . . no N1 C6 C4 118(3) . . . ? N1 C6 C5 123(3) . . . ? C4 C6 C5 118(2) . . . ? N2 C7 C8 129(2) . . . ? N2 C7 C9 112(2) . . . ? C8 C7 C9 118(2) . . . ? C7 C8 C10 120(2) . . . ? C7 C8 H6 140.7 . . . no C10 C8 H6 99.3 . . . no C7 C9 C11 124(2) . . . ? C7 C9 H7 114.4 . . . no C11 C9 H7 121.8 . . . no C8 C10 C12 120(2) . . . ? C8 C10 H8 131.0 . . . no C12 C10 H8 109.0 . . . no C9 C11 C12 117(2) . . . ? C9 C11 H9 116.5 . . . no C12 C11 H9 126.8 . . . no O1 C12 C10 114(2) . . . ? O1 C12 C11 124(2) . . . ? C10 C12 C11 121(2) . . . ? O1 C13 C14 101(1) . . . ? O1 C13 H10 119.2 . . . no O1 C13 H11 134.5 . . . no C14 C13 H10 64.0 . . . no C14 C13 H11 71.7 . . . no H10 C13 H11 98.1 . . . no C13 C14 C15 113(1) . . . ? C13 C14 H12 119.7 . . . no C13 C14 H13 133.4 . . . no C15 C14 H12 78.7 . . . no C15 C14 H13 78.5 . . . no H12 C14 H13 106.8 . . . no C14 C15 C16 112(1) . . . ? C14 C15 H14 122.8 . . . no C14 C15 H15 119.6 . . . no C16 C15 H14 99.5 . . . no C16 C15 H15 93.6 . . . no H14 C15 H15 103.6 . . . no C15 C16 C17 117(1) . . . ? C15 C16 H16 119.0 . . . no C15 C16 H17 113.0 . . . no C17 C16 H16 102.0 . . . no C17 C16 H17 102.7 . . . no H16 C16 H17 101.1 . . . no C16 C17 C18 115(1) . . . ? C16 C17 H18 113.5 . . . no C16 C17 H19 113.8 . . . no C18 C17 H18 106.9 . . . no C18 C17 H19 111.4 . . . no H18 C17 H19 94.1 . . . no C17 C18 C19 116(2) . . . ? C17 C18 H20 102.1 . . . no C17 C18 H21 106.6 . . . no C19 C18 H20 112.1 . . . no C19 C18 H21 118.0 . . . no H20 C18 H21 100.1 . . . no C18 C19 C20 116(2) . . . ? C18 C19 H22 104.9 . . . no C18 C19 H23 109.6 . . . no C20 C19 H22 109.7 . . . no C20 C19 H23 110.6 . . . no H22 C19 H23 105.7 . . . no C19 C20 C21 116(2) . . . ? C19 C20 H24 106.7 . . . no C19 C20 H25 106.7 . . . no C21 C20 H24 113.7 . . . no C21 C20 H25 111.8 . . . no H24 C20 H25 99.9 . . . no C20 C21 C22 119(2) . . . ? C20 C21 H26 109.0 . . . no C20 C21 H27 107.0 . . . no C22 C21 H26 109.9 . . . no C22 C21 H27 107.2 . . . no H26 C21 H27 104.1 . . . no C21 C22 C23 115(2) . . . ? C21 C22 H28 109.4 . . . no C21 C22 H29 104.7 . . . no C23 C22 H28 115.2 . . . no C23 C22 H29 112.4 . . . no H28 C22 H29 98.0 . . . no O2 C23 C22 112(2) . . . ? O2 C23 H30 121.9 . . . no O2 C23 H31 122.5 . . . no C22 C23 H30 95.8 . . . no C22 C23 H31 99.9 . . . no H30 C23 H31 100.1 . . . no O2 C24 O3 124(2) . . . ? O2 C24 C25 112(2) . . . ? O3 C24 C25 123(2) . . . ? C24 C25 C26 106(1) . . . ? C24 C25 C27 112(1) . . . ? C24 C25 H32 115.3 . . . no C26 C25 C27 107(1) . . . ? C26 C25 H32 113.5 . . . no C27 C25 H32 103.1 . . . no C25 C26 C28 113(1) . . . ? C25 C26 H33 109.9 . . . no C25 C26 H34 108.8 . . . no C28 C26 H33 102.6 . . . no C28 C26 H34 116.9 . . . no H33 C26 H34 104.6 . . . no C25 C27 C29 114(1) . . . ? C25 C27 H35 107.4 . . . no C25 C27 H36 108.1 . . . no C29 C27 H35 117.7 . . . no C29 C27 H36 113.2 . . . no H35 C27 H36 94.7 . . . no N3 C28 C26 113(1) . . . ? N3 C28 C30 110(1) . . . ? N3 C28 C31 109(1) . . . ? C26 C28 C30 110(1) . . . ? C26 C28 C31 109(2) . . . ? C30 C28 C31 106(1) . . . ? N3 C29 C27 112(1) . . . ? N3 C29 C32 109(1) . . . ? N3 C29 C33 112(1) . . . ? C27 C29 C32 107(1) . . . ? C27 C29 C33 109(1) . . . ? C32 C29 C33 108(1) . . . ? C28 C30 H37 118.7 . . . no C28 C30 H38 120.2 . . . no C28 C30 H39 112.2 . . . no H37 C30 H38 101.0 . . . no H37 C30 H39 97.7 . . . no H38 C30 H39 103.8 . . . no C28 C31 H40 122.2 . . . no C28 C31 H41 112.6 . . . no C28 C31 H42 108.0 . . . no H40 C31 H41 102.3 . . . no H40 C31 H42 106.7 . . . no H41 C31 H42 103.3 . . . no C29 C32 H43 107.4 . . . no C29 C32 H44 113.5 . . . no C29 C32 H45 125.4 . . . no H43 C32 H44 100.9 . . . no H43 C32 H45 102.5 . . . no H44 C32 H45 103.9 . . . no C29 C33 H46 113.9 . . . no C29 C33 H47 122.9 . . . no C29 C33 H48 117.6 . . . no H46 C33 H47 98.2 . . . no H46 C33 H48 103.0 . . . no H47 C33 H48 97.8 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C10 3.61(2) . 3_958 no O3 C11 3.32(2) . 3_657 no O3 C13 3.34(2) . 3_657 no O4 C3 3.57(3) . 2_657 no #============================================================================== data_azoc11p _database_code_depnum_ccdc_archive 'CCDC 240930' #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows v1.06 (MSC, 1997-99)' _computing_structure_solution ; SHELX97 (Sheldrick, 1997) ; _computing_structure_refinement 'CRYSTALS (Watkin et al 2001)' _computing_publication_material 'teXsan for Windows v1.06 (MSC, 1997-99)' #------------------------------------------------------------------------------ _cell_length_a 6.6750(7) _cell_length_b 11.850(2) _cell_length_c 20.811(2) _cell_angle_alpha 75.756(8) _cell_angle_beta 81.813(3) _cell_angle_gamma 75.557(2) _cell_volume 1539.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #------------------------------------------------------------------------------ _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-p 1' loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 536.74 _chemical_formula_analytical ? _chemical_formula_sum ' C32 H46 N3 O4 ' _chemical_formula_moiety ' C32 H46 N3 O4 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 582.000 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ; HIGASHI, T. (1995). Abscor - Empirical Absorption Correction, Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.7692 #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'Quantum CCD' _diffrn_measurement_device 'Rigaku AFC7' _diffrn_measurement_method 'Phi + Omega' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 8022 _reflns_number_total 4337 _reflns_number_gt 1995 _reflns_threshold_expression I>3.00\s(I) _diffrn_reflns_av_R_equivalents 0.11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.01 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_reduction_process 'Lp corrections applied' #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 64 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 90 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 6 0.004 0.003 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 8 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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_occupancy _atom_site_adp_type _atom_site_attached_hydrogens O1 O -1.2842(8) 1.4156(5) 0.5693(3) 0.0747 1.0000 Uani . O2 O 0.6177(8) 0.8067(5) 0.2230(2) 0.0653 1.0000 Uani . O3 O 0.9157(9) 0.7273(6) 0.2663(3) 0.0913 1.0000 Uani . O4 O 1.127(1) 0.8253(5) -0.0038(3) 0.0957 1.0000 Uani . N1 N -2.0175(11) 1.6669(6) 0.7360(3) 0.0619 1.0000 Uani . N2 N -1.8414(11) 1.6182(6) 0.7536(3) 0.0727 1.0000 Uani . N3 N 1.0827(9) 0.7697(6) 0.0559(3) 0.0610 1.0000 Uani . C1 C -2.445(2) 1.8146(9) 0.8769(7) 0.1131 1.0000 Uani . C2 C -2.237(2) 1.7849(9) 0.8858(5) 0.1033 1.0000 Uani . C3 C -2.5084(15) 1.798(1) 0.8208(7) 0.1076 1.0000 Uani . C4 C -2.0953(14) 1.7384(7) 0.8419(5) 0.0757 1.0000 Uani . C5 C -2.3610(15) 1.7535(9) 0.7754(5) 0.0928 1.0000 Uani . C6 C -2.1562(14) 1.7203(7) 0.7854(4) 0.0634 1.0000 Uani . C7 C -1.7070(13) 1.5661(7) 0.7039(4) 0.0584 1.0000 Uani . C8 C -1.5109(13) 1.5095(7) 0.7222(4) 0.0671 1.0000 Uani . C9 C -1.7604(12) 1.5705(7) 0.6414(4) 0.0605 1.0000 Uani . C10 C -1.3617(12) 1.4577(7) 0.6796(3) 0.0638 1.0000 Uani . C11 C -1.6123(12) 1.5215(7) 0.5974(4) 0.0624 1.0000 Uani . C12 C -1.4108(12) 1.4625(7) 0.6178(4) 0.0593 1.0000 Uani . C13 C -1.0765(11) 1.3585(7) 0.5833(4) 0.0540 1.0000 Uani . C14 C -0.9668(11) 1.3161(7) 0.5222(3) 0.0543 1.0000 Uani . C15 C -0.7400(11) 1.2572(6) 0.5260(4) 0.0553 1.0000 Uani . C16 C -0.6467(11) 1.2158(7) 0.4641(3) 0.0559 1.0000 Uani . C17 C -0.4190(11) 1.1555(7) 0.4649(3) 0.0589 1.0000 Uani . C18 C -0.3277(11) 1.1141(8) 0.4014(4) 0.0664 1.0000 Uani . C19 C -0.0973(11) 1.0566(7) 0.4002(4) 0.0584 1.0000 Uani . C20 C -0.0088(11) 1.0091(7) 0.3395(4) 0.0622 1.0000 Uani . C21 C 0.2225(12) 0.9537(7) 0.3393(4) 0.0633 1.0000 Uani . C22 C 0.3173(12) 0.9055(8) 0.2776(4) 0.0720 1.0000 Uani . C23 C 0.5387(13) 0.8442(9) 0.2843(4) 0.0856 1.0000 Uani . C24 C 0.8143(14) 0.7487(8) 0.2218(4) 0.0657 1.0000 Uani . C25 C 0.8913(11) 0.7173(7) 0.1555(4) 0.0532 1.0000 Uani . C26 C 1.0974(11) 0.6320(7) 0.1546(3) 0.0544 1.0000 Uani . C27 C 1.1821(13) 0.6444(7) 0.0832(4) 0.0619 1.0000 Uani . C28 C 0.9204(11) 0.8268(7) 0.1007(3) 0.0531 1.0000 Uani . C29 C 1.4144(12) 0.626(1) 0.0718(5) 0.0977 1.0000 Uani . C30 C 1.1144(15) 0.5698(9) 0.0468(5) 0.1011 1.0000 Uani . C31 C 1.0048(13) 0.9177(7) 0.1236(4) 0.0725 1.0000 Uani . C32 C 0.7251(11) 0.8906(7) 0.0648(3) 0.0757 1.0000 Uani . H1 H -2.559(2) 1.8572(9) 0.9057(7) 0.0507 1.0000 Uiso . H2 H -2.195(2) 1.8031(9) 0.9309(5) 0.0507 1.0000 Uiso . H3 H -2.6708(15) 1.820(1) 0.8125(7) 0.0507 1.0000 Uiso . H4 H -1.9362(14) 1.7164(7) 0.8512(5) 0.0507 1.0000 Uiso . H5 H -2.4167(15) 1.7403(9) 0.7319(5) 0.0507 1.0000 Uiso . H6 H -1.4759(13) 1.5086(7) 0.7675(4) 0.0507 1.0000 Uiso . H7 H -1.9111(12) 1.6190(7) 0.6277(4) 0.0507 1.0000 Uiso . H8 H -1.2228(12) 1.4094(7) 0.6940(3) 0.0507 1.0000 Uiso . H9 H -1.6537(12) 1.5222(7) 0.5539(4) 0.0507 1.0000 Uiso . H10 H -0.9863(11) 1.4011(7) 0.5981(4) 0.0507 1.0000 Uiso . H11 H -1.0542(11) 1.2802(7) 0.6195(4) 0.0507 1.0000 Uiso . H12 H -1.0342(11) 1.2695(7) 0.5052(3) 0.0507 1.0000 Uiso . H13 H -0.9756(11) 1.3929(7) 0.4827(3) 0.0507 1.0000 Uiso . H14 H -0.6660(11) 1.3154(6) 0.5371(4) 0.0507 1.0000 Uiso . H15 H -0.7284(11) 1.1943(6) 0.5672(4) 0.0507 1.0000 Uiso . H16 H -0.7252(11) 1.1654(7) 0.4573(3) 0.0507 1.0000 Uiso . H17 H -0.6685(11) 1.2879(7) 0.4265(3) 0.0507 1.0000 Uiso . H18 H -0.3400(11) 1.2125(7) 0.4735(3) 0.0507 1.0000 Uiso . H19 H -0.3965(11) 1.0898(7) 0.5035(3) 0.0507 1.0000 Uiso . H20 H -0.3923(11) 1.0599(8) 0.3945(4) 0.0507 1.0000 Uiso . H21 H -0.3410(11) 1.1837(8) 0.3638(4) 0.0507 1.0000 Uiso . H22 H -0.0112(11) 1.1137(7) 0.4013(4) 0.0507 1.0000 Uiso . H23 H -0.0627(11) 0.9919(7) 0.4375(4) 0.0507 1.0000 Uiso . H24 H -0.0799(11) 0.9467(7) 0.3357(4) 0.0507 1.0000 Uiso . H25 H -0.0374(11) 1.0702(7) 0.2986(4) 0.0507 1.0000 Uiso . H26 H 0.2894(12) 1.0203(7) 0.3404(4) 0.0507 1.0000 Uiso . H27 H 0.2468(12) 0.8971(7) 0.3779(4) 0.0507 1.0000 Uiso . H28 H 0.2237(12) 0.8556(8) 0.2699(4) 0.0507 1.0000 Uiso . H29 H 0.3009(12) 0.9711(8) 0.2363(4) 0.0507 1.0000 Uiso . H30 H 0.5289(13) 0.7746(9) 0.3267(4) 0.0507 1.0000 Uiso . H31 H 0.6005(13) 0.8941(9) 0.3020(4) 0.0507 1.0000 Uiso . H32 H 0.7829(11) 0.6812(7) 0.1371(4) 0.0507 1.0000 Uiso . H33 H 1.1857(11) 0.6448(7) 0.1846(3) 0.0507 1.0000 Uiso . H34 H 1.0932(11) 0.5441(7) 0.1734(3) 0.0507 1.0000 Uiso . H35 H 1.4690(12) 0.621(1) 0.1125(5) 0.0507 1.0000 Uiso . H36 H 1.4722(12) 0.555(1) 0.0564(5) 0.0507 1.0000 Uiso . H37 H 1.4487(12) 0.692(1) 0.0395(5) 0.0507 1.0000 Uiso . H38 H 1.0473(15) 0.5145(9) 0.0778(5) 0.0507 1.0000 Uiso . H39 H 1.0211(15) 0.6179(9) 0.0151(5) 0.0507 1.0000 Uiso . H40 H 1.2330(15) 0.5275(9) 0.0246(5) 0.0507 1.0000 Uiso . H41 H 0.9937(13) 0.9036(7) 0.1747(4) 0.0507 1.0000 Uiso . H42 H 1.1555(13) 0.9050(7) 0.1132(4) 0.0507 1.0000 Uiso . H43 H 0.9494(13) 1.0014(7) 0.1102(4) 0.0507 1.0000 Uiso . H44 H 0.5937(11) 0.9250(7) 0.0893(3) 0.0507 1.0000 Uiso . H45 H 0.7396(11) 0.9515(7) 0.0251(3) 0.0507 1.0000 Uiso . H46 H 0.6727(11) 0.8303(7) 0.0462(3) 0.0507 1.0000 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.060(4) 0.096(5) 0.061(4) -0.029(3) -0.017(3) 0.016(3) O2 0.051(4) 0.090(4) 0.054(3) -0.023(3) -0.002(3) -0.009(3) O3 0.065(4) 0.139(6) 0.059(4) -0.027(4) -0.016(3) 0.010(3) O4 0.125(5) 0.078(5) 0.061(4) -0.008(3) 0.031(3) -0.010(4) N1 0.070(5) 0.060(5) 0.055(4) -0.025(4) 0.013(4) -0.013(4) N2 0.057(5) 0.068(5) 0.076(5) -0.001(4) -0.016(4) 0.010(4) N3 0.071(4) 0.051(5) 0.056(4) -0.014(3) 0.011(3) -0.012(4) C1 0.122(11) 0.071(8) 0.125(11) -0.044(7) 0.074(9) -0.009(7) C2 0.14(1) 0.102(9) 0.057(6) -0.032(6) 0.040(7) -0.022(8) C3 0.049(7) 0.119(9) 0.146(11) -0.044(8) 0.019(7) -0.002(6) C4 0.077(6) 0.074(7) 0.069(6) -0.017(5) 0.015(5) -0.015(5) C5 0.062(7) 0.105(8) 0.123(9) -0.042(7) 0.007(6) -0.030(6) C6 0.076(7) 0.045(6) 0.066(6) -0.010(5) 0.018(5) -0.025(5) C7 0.066(6) 0.053(6) 0.050(5) -0.028(5) 0.028(5) -0.002(5) C8 0.074(6) 0.085(7) 0.042(5) -0.036(5) -0.009(5) 0.007(5) C9 0.072(6) 0.049(6) 0.056(5) -0.015(4) -0.001(5) -0.006(4) C10 0.076(6) 0.085(7) 0.025(4) -0.015(4) -0.014(4) -0.002(5) C11 0.066(6) 0.069(6) 0.055(5) -0.019(5) -0.001(4) -0.018(5) C12 0.054(6) 0.060(6) 0.059(6) -0.022(5) -0.003(4) 0.004(5) C13 0.057(5) 0.054(6) 0.054(5) -0.017(4) -0.020(4) -0.003(4) C14 0.061(6) 0.061(6) 0.045(4) -0.021(4) -0.008(4) -0.011(5) C15 0.044(5) 0.058(6) 0.059(5) -0.016(4) 0.000(4) -0.002(4) C16 0.048(5) 0.064(6) 0.059(5) -0.027(5) -0.002(4) -0.008(4) C17 0.056(5) 0.077(6) 0.045(5) -0.021(4) 0.001(4) -0.013(5) C18 0.049(5) 0.090(7) 0.059(5) -0.021(5) -0.002(4) -0.008(5) C19 0.052(6) 0.073(6) 0.056(5) -0.020(4) 0.008(4) -0.024(5) C20 0.053(6) 0.082(6) 0.051(5) -0.022(5) -0.003(4) -0.009(5) C21 0.066(6) 0.069(6) 0.058(5) -0.017(4) 0.024(4) -0.034(5) C22 0.064(7) 0.093(7) 0.057(5) -0.013(5) 0.005(4) -0.023(6) C23 0.074(7) 0.140(9) 0.039(5) -0.044(5) 0.001(4) 0.003(6) C24 0.053(6) 0.083(7) 0.057(6) -0.025(5) 0.005(5) -0.004(5) C25 0.051(5) 0.046(5) 0.064(5) -0.021(4) 0.000(4) -0.010(4) C26 0.068(5) 0.060(5) 0.028(4) -0.009(4) -0.002(3) -0.003(4) C27 0.075(6) 0.051(6) 0.067(5) -0.026(5) -0.020(5) -0.007(5) C28 0.068(5) 0.035(5) 0.046(4) -0.010(4) 0.013(4) -0.002(4) C29 0.064(6) 0.122(9) 0.102(7) -0.034(6) 0.007(5) -0.009(6) C30 0.117(8) 0.085(8) 0.094(7) -0.033(6) 0.020(6) -0.013(6) C31 0.106(6) 0.054(6) 0.064(5) -0.016(4) 0.003(5) -0.032(5) C32 0.074(5) 0.095(7) 0.037(4) -0.008(4) -0.021(4) 0.024(5) #============================================================================== # 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 ; Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 21.7 13.5 19.2 11.3 2.06 ; _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1995 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.2980 _refine_ls_R_factor_gt 0.1767 _refine_ls_wR_factor_all 0.1370 _refine_ls_wR_factor_ref 0.0813 _refine_ls_goodness_of_fit_ref 1.1465 _refine_ls_shift/su_max 0.000089 _refine_diff_density_min -0.49 _refine_diff_density_max 0.46 #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C12 . 1.357(8) yes O1 . C13 . 1.420(8) yes O2 . C23 . 1.441(8) yes O2 . C24 . 1.321(9) yes O3 . C24 . 1.164(9) yes O4 . N3 . 1.287(7) yes N1 . N2 . 1.237(8) yes N1 . C6 . 1.44(1) yes N2 . C7 . 1.424(9) yes N3 . C27 . 1.472(9) yes N3 . C28 . 1.469(8) yes C1 . C2 . 1.372(15) yes C1 . C3 . 1.367(14) yes C1 . H1 . 1.010 no C2 . C4 . 1.333(11) yes C2 . H2 . 1.102 no C3 . C5 . 1.366(12) yes C3 . H3 . 1.079 no C4 . C6 . 1.378(11) yes C4 . H4 . 1.062 no C5 . C6 . 1.356(11) yes C5 . H5 . 1.084 no C7 . C8 . 1.37(1) yes C7 . C9 . 1.38(1) yes C8 . C10 . 1.365(9) yes C8 . H6 . 1.001 no C9 . C11 . 1.368(9) yes C9 . H7 . 1.066 no C10 . C12 . 1.355(9) yes C10 . H8 . 1.004 no C11 . C12 . 1.42(1) yes C11 . H9 . 0.982 no C13 . C14 . 1.506(9) yes C13 . H10 . 0.997 no C13 . H11 . 1.034 no C14 . C15 . 1.505(8) yes C14 . H12 . 0.947 no C14 . H13 . 1.062 no C15 . C16 . 1.489(8) yes C15 . H14 . 1.027 no C15 . H15 . 0.987 no C16 . C17 . 1.510(9) yes C16 . H16 . 0.933 no C16 . H17 . 1.002 no C17 . C18 . 1.517(9) yes C17 . H18 . 1.015 no C17 . H19 . 0.971 no C18 . C19 . 1.518(8) yes C18 . H20 . 0.906 no C18 . H21 . 0.983 no C19 . C20 . 1.495(9) yes C19 . H22 . 0.997 no C19 . H23 . 0.956 no C20 . C21 . 1.519(9) yes C20 . H24 . 0.996 no C20 . H25 . 0.979 no C21 . C22 . 1.52(1) yes C21 . H26 . 1.006 no C21 . H27 . 0.917 no C22 . C23 . 1.48(1) yes C22 . H28 . 1.014 no C22 . H29 . 1.005 no C23 . H30 . 1.056 no C23 . H31 . 0.962 no C24 . C25 . 1.50(1) yes C25 . C26 . 1.491(9) yes C25 . C28 . 1.535(9) yes C25 . H32 . 1.081 no C26 . C27 . 1.50(1) yes C26 . H33 . 0.978 no C26 . H34 . 1.025 no C27 . C29 . 1.50(1) yes C27 . C30 . 1.479(11) yes C28 . C31 . 1.53(1) yes C28 . C32 . 1.529(9) yes C29 . H35 . 0.950 no C29 . H36 . 0.950 no C29 . H37 . 0.950 no C30 . H38 . 0.950 no C30 . H39 . 0.950 no C30 . H40 . 0.950 no C31 . H41 . 1.028 no C31 . H42 . 0.980 no C31 . H43 . 0.953 no C32 . H44 . 0.997 no C32 . H45 . 0.965 no C32 . H46 . 1.039 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C12 . O1 . C13 . 117.2(6) yes C23 . O2 . C24 . 113.8(6) yes N2 . N1 . C6 . 114.0(8) yes N1 . N2 . C7 . 112.9(7) yes O4 . N3 . C27 . 123.1(6) yes O4 . N3 . C28 . 121.4(6) yes C27 . N3 . C28 . 115.4(6) yes C2 . C1 . C3 . 119.1(9) yes C2 . C1 . H1 . 125.9(7) no C3 . C1 . H1 . 114.6(7) no C1 . C2 . C4 . 121.8(11) yes C1 . C2 . H2 . 115.9(7) no C4 . C2 . H2 . 122.2(7) no C1 . C3 . C5 . 118.5(10) yes C1 . C3 . H3 . 121.0(7) no C5 . C3 . H3 . 120.4(7) no C2 . C4 . C6 . 119.9(10) yes C2 . C4 . H4 . 119.0(7) no C6 . C4 . H4 . 121.1(5) no C3 . C5 . C6 . 122.2(11) yes C3 . C5 . H5 . 116.5(7) no C6 . C5 . H5 . 121.1(6) no N1 . C6 . C4 . 124.6(9) yes N1 . C6 . C5 . 117.1(9) yes C4 . C6 . C5 . 118.3(8) yes N2 . C7 . C8 . 114.5(8) yes N2 . C7 . C9 . 125.0(8) yes C8 . C7 . C9 . 120.5(7) yes C7 . C8 . C10 . 121.8(7) yes C7 . C8 . H6 . 118.7(5) no C10 . C8 . H6 . 119.4(5) no C7 . C9 . C11 . 118.8(7) yes C7 . C9 . H7 . 118.8(5) no C11 . C9 . H7 . 122.1(5) no C8 . C10 . C12 . 118.5(7) yes C8 . C10 . H8 . 122.2(5) no C12 . C10 . H8 . 119.0(5) no C9 . C11 . C12 . 119.5(8) yes C9 . C11 . H9 . 118.0(5) no C12 . C11 . H9 . 122.3(5) no O1 . C12 . C10 . 126.8(7) yes O1 . C12 . C11 . 112.3(7) yes C10 . C12 . C11 . 120.9(7) yes O1 . C13 . C14 . 107.5(6) yes O1 . C13 . H10 . 120.9(4) no C14 . C13 . H10 . 107.9(4) no O1 . C13 . H11 . 117.2(4) no C14 . C13 . H11 . 101.9(4) no H10 . C13 . H11 . 99.604 no C13 . C14 . C15 . 115.8(7) yes C13 . C14 . H12 . 115.5(4) no C15 . C14 . H12 . 109.9(4) no C13 . C14 . H13 . 106.7(4) no C15 . C14 . H13 . 106.5(4) no H12 . C14 . H13 . 100.900 no C14 . C15 . C16 . 111.8(6) yes C14 . C15 . H14 . 108.4(4) no C16 . C15 . H14 . 113.1(4) no C14 . C15 . H15 . 107.0(4) no C16 . C15 . H15 . 115.1(4) no H14 . C15 . H15 . 100.774 no C15 . C16 . C17 . 114.3(6) yes C15 . C16 . H16 . 107.2(4) no C17 . C16 . H16 . 111.4(4) no C15 . C16 . H17 . 106.8(4) no C17 . C16 . H17 . 110.2(4) no H16 . C16 . H17 . 106.526 no C16 . C17 . C18 . 113.3(6) yes C16 . C17 . H18 . 108.9(4) no C18 . C17 . H18 . 110.2(5) no C16 . C17 . H19 . 110.2(4) no C18 . C17 . H19 . 111.0(4) no H18 . C17 . H19 . 102.689 no C17 . C18 . C19 . 114.2(6) yes C17 . C18 . H20 . 111.0(5) no C19 . C18 . H20 . 106.8(4) no C17 . C18 . H21 . 109.1(4) no C19 . C18 . H21 . 105.3(4) no H20 . C18 . H21 . 110.357 no C18 . C19 . C20 . 114.5(7) yes C18 . C19 . H22 . 112.5(4) no C20 . C19 . H22 . 104.2(4) no C18 . C19 . H23 . 113.1(4) no C20 . C19 . H23 . 106.4(4) no H22 . C19 . H23 . 105.182 no C19 . C20 . C21 . 113.4(7) yes C19 . C20 . H24 . 110.2(4) no C21 . C20 . H24 . 107.6(5) no C19 . C20 . H25 . 111.8(4) no C21 . C20 . H25 . 109.9(4) no H24 . C20 . H25 . 103.496 no C20 . C21 . C22 . 114.5(7) yes C20 . C21 . H26 . 105.3(5) no C22 . C21 . H26 . 107.8(5) no C20 . C21 . H27 . 108.9(4) no C22 . C21 . H27 . 112.4(4) no H26 . C21 . H27 . 107.462 no C21 . C22 . C23 . 110.7(7) yes C21 . C22 . H28 . 107.1(5) no C23 . C22 . H28 . 115.9(5) no C21 . C22 . H29 . 110.9(4) no C23 . C22 . H29 . 111.3(5) no H28 . C22 . H29 . 100.441 no O2 . C23 . C22 . 106.8(6) yes O2 . C23 . H30 . 115.5(5) no C22 . C23 . H30 . 102.2(5) no O2 . C23 . H31 . 123.0(5) no C22 . C23 . H31 . 106.9(5) no H30 . C23 . H31 . 100.385 no O2 . C24 . O3 . 123.9(7) yes O2 . C24 . C25 . 111.5(8) yes O3 . C24 . C25 . 124.6(8) yes C24 . C25 . C26 . 114.3(7) yes C24 . C25 . C28 . 112.4(6) yes C26 . C25 . C28 . 104.5(6) yes C24 . C25 . H32 . 112.6(5) no C26 . C25 . H32 . 107.9(4) no C28 . C25 . H32 . 104.3(4) no C25 . C26 . C27 . 106.7(6) yes C25 . C26 . H33 . 110.7(4) no C27 . C26 . H33 . 115.8(4) no C25 . C26 . H34 . 114.8(4) no C27 . C26 . H34 . 107.6(4) no H33 . C26 . H34 . 101.461 no N3 . C27 . C26 . 100.5(6) yes N3 . C27 . C29 . 110.2(7) yes C26 . C27 . C29 . 114.9(7) yes N3 . C27 . C30 . 107.3(7) yes C26 . C27 . C30 . 114.8(8) yes C29 . C27 . C30 . 108.6(8) yes N3 . C28 . C25 . 100.3(5) yes N3 . C28 . C31 . 108.0(6) yes C25 . C28 . C31 . 114.4(6) yes N3 . C28 . C32 . 110.7(6) yes C25 . C28 . C32 . 113.5(6) yes C31 . C28 . C32 . 109.5(6) yes C27 . C29 . H35 . 109.1(5) no C27 . C29 . H36 . 110.1(5) no H35 . C29 . H36 . 109.471 no C27 . C29 . H37 . 109.2(5) no H35 . C29 . H37 . 109.469 no H36 . C29 . H37 . 109.478 no C27 . C30 . H38 . 108.8(5) no C27 . C30 . H39 . 110.7(5) no H38 . C30 . H39 . 109.467 no C27 . C30 . H40 . 108.9(5) no H38 . C30 . H40 . 109.478 no H39 . C30 . H40 . 109.465 no C28 . C31 . H41 . 111.8(4) no C28 . C31 . H42 . 110.6(4) no H41 . C31 . H42 . 101.127 no C28 . C31 . H43 . 121.5(4) no H41 . C31 . H43 . 102.994 no H42 . C31 . H43 . 106.705 no C28 . C32 . H44 . 121.2(3) no C28 . C32 . H45 . 117.3(4) no H44 . C32 . H45 . 104.541 no C28 . C32 . H46 . 109.9(4) no H44 . C32 . H46 . 99.303 no H45 . C32 . H46 . 101.438 no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================