# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 # #------------------------------------------------------------------------- #2 Person making the deposition # _publ_contact_author ; Dr Gilles Guichard Intitut de Biologie Mol\'eculaire et Cellulaire CNRS UPR 9021 15 rue Descartes Strasbourg 67084 FRANCE ; _publ_contact_author_email G.GUICHARD@IBMC.U-STRASBG.FR #------------------------------------------------------------------------- #3 Publication details loop_ _publ_author_name _publ_author_address A.-P.Schaffner ; Immunologie et Chimie Th\'erapeutiques, UPR 9021 CNRS, Institut de Biologie Mol\'eculaire et Cellulaire 15, rue Descartes, 67000 Strasbourg, France ; G.Lena ; Immunologie et Chimie Th\'erapeutiques, UPR 9021 CNRS, Institut de Biologie Mol\'eculaire et Cellulaire 15, rue Descartes, 67000 Strasbourg, France ; S.Roussel ; Immunologie et Chimie Th\'erapeutiques, UPR 9021 CNRS, Institut de Biologie Mol\'eculaire et Cellulaire 15, rue Descartes, 67000 Strasbourg, France ; A.Aubry ; Laboratoire de Cristallographie et Mod\'elisation des Mat\'eriaux Min\'eraux et Biologiques (LCM3B), Groupe Biocristallographie, UMR n\% 7036 CNRS-Universit\'e Henri Poincar\'e, Nancy I, B.P. 239, F-54506 Vandoeuvre l\`es Nancy CEDEX, France ; J.-P.Briand ; Immunologie et Chimie Th\'erapeutiques, UPR 9021 CNRS, Institut de Biologie Mol\'eculaire et Cellulaire 15, rue Descartes, 67000 Strasbourg, France ; ; C.Didierjean ; ; Laboratoire de Cristallographie et Mod\'elisation des Mat\'eriaux Min\'eraux et Biologiques (LCM3B), Groupe Biocristallographie, UMR n\% 7036 CNRS-Universit\'e Henri Poincar\'e, Nancy I, B.P. 239, F-54506 Vandoeuvre l\`es Nancy CEDEX, France ; G.Guichard ; Immunologie et Chimie Th\'erapeutiques, UPR 9021 CNRS, Institut de Biologie Mol\'eculaire et Cellulaire 15, rue Descartes, 67000 Strasbourg, France ; _journal_volume ? _journal_page_first ? _journal_page_last ? _journal_year ? _publ_contact_author_name 'Dr Gilles Guichard' # #------------------------------------------------------------------------- #4 Chemical and physical data data_shelxl _database_code_depnum_ccdc_archive 'CCDC 603581' _audit_creation_date 2006-05-26T10:15:09-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H15 N3 O2' _chemical_formula_sum 'C12 H15 N3 O2' _chemical_formula_weight 233.27 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M 'P 61' _symmetry_space_group_name_Hall 'P 61' _symmetry_Int_Tables_number 169 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' 'x-y, x, z+1/6' 'y, -x+y, z+5/6' _cell_length_a 15.583(2) _cell_length_b 15.583(2) _cell_length_c 9.964(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 2095.4(4) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.29 _cell_measurement_theta_max 25.98 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.109 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.634 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.5406 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.0132 _diffrn_reflns_number 1380 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 5.51 _diffrn_reflns_theta_max 69.69 _diffrn_reflns_theta_full 69.69 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_total 1380 _reflns_number_gt 1302 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_reduction 'maXus (Mackay et al., 1999)' _computing_structure_solution 'SIR_92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0909P)^2^+0.0880P] 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_number_reflns 1380 _refine_ls_number_parameters 160 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1246 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.13 _refine_ls_restrained_S_all 1.129 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(4) _refine_diff_density_max 0.196 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.053 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.4159(2) 0.1877(2) 0.1722(3) 0.0488(6) Uani 1 1 d . . . H1A H 0.4007 0.1829 0.0771 0.063 Uiso 1 1 calc R . . H1B H 0.3947 0.1214 0.2047 0.063 Uiso 1 1 calc R . . N1 N 0.36023(19) 0.22544(19) 0.2409(3) 0.0543(6) Uani 1 1 d . . . C2 C 0.3104(4) 0.2683(5) 0.1632(5) 0.0958(15) Uani 1 1 d . . . H2A H 0.318 0.2608 0.069 0.144 Uiso 1 1 calc R . . H2B H 0.3395 0.3374 0.1843 0.144 Uiso 1 1 calc R . . H2C H 0.2412 0.2347 0.1855 0.144 Uiso 1 1 calc R . . C3 C 0.35804(19) 0.22819(19) 0.3753(3) 0.0467(6) Uani 1 1 d . . . O1 O 0.31604(17) 0.26383(18) 0.4390(2) 0.0627(6) Uani 1 1 d . . . C4 C 0.41283(18) 0.18137(17) 0.4471(2) 0.0384(5) Uani 1 1 d . . . H4 H 0.3891 0.115 0.41 0.046 Uiso 1 1 calc R . . C5 C 0.3915(2) 0.17170(19) 0.5972(3) 0.0458(6) Uani 1 1 d . . . H5A H 0.4259 0.2372 0.6373 0.06 Uiso 1 1 calc R . . H5B H 0.321 0.1452 0.6106 0.06 Uiso 1 1 calc R . . C6 C 0.42220(18) 0.10607(17) 0.6691(2) 0.0405(5) Uani 1 1 d . . . C7 C 0.3799(2) 0.0062(2) 0.6341(3) 0.0560(7) Uani 1 1 d . . . H7 H 0.3333 -0.0197 0.5655 0.073 Uiso 1 1 calc R . . C8 C 0.4074(3) -0.0544(3) 0.7012(4) 0.0732(10) Uani 1 1 d . . . H8 H 0.3794 -0.1207 0.6771 0.095 Uiso 1 1 calc R . . C9 C 0.4758(3) -0.0166(3) 0.8034(5) 0.0741(10) Uani 1 1 d . . . H9 H 0.4937 -0.0575 0.8486 0.096 Uiso 1 1 calc R . . C10 C 0.5178(2) 0.0815(3) 0.8387(4) 0.0673(9) Uani 1 1 d . . . H10 H 0.5644 0.1069 0.9074 0.087 Uiso 1 1 calc R . . C11 C 0.4910(2) 0.1428(2) 0.7722(3) 0.0516(6) Uani 1 1 d . . . H11 H 0.5194 0.2091 0.797 0.067 Uiso 1 1 calc R . . N2 N 0.52064(15) 0.24074(15) 0.4252(2) 0.0406(5) Uani 1 1 d D . . C12 C 0.57083(18) 0.27167(16) 0.3078(3) 0.0385(5) Uani 1 1 d . . . O2 O 0.66381(14) 0.32330(14) 0.3088(2) 0.0458(4) Uani 1 1 d . . . N3 N 0.52268(17) 0.24846(18) 0.1897(2) 0.0476(6) Uani 1 1 d D . . H2 H 0.558(2) 0.269(3) 0.513(2) 0.062 Uiso 1 1 d D . . H3 H 0.562(2) 0.279(2) 0.103(2) 0.062 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0522(14) 0.0469(13) 0.0387(13) 0.0004(11) -0.0048(11) 0.0184(11) N1 0.0592(14) 0.0618(14) 0.0487(14) 0.0093(11) -0.0025(11) 0.0355(12) C2 0.119(4) 0.145(4) 0.069(2) 0.031(3) 0.002(2) 0.099(3) C3 0.0438(12) 0.0454(13) 0.0551(17) 0.0095(12) 0.0047(11) 0.0256(11) O1 0.0747(13) 0.0759(13) 0.0641(14) 0.0163(11) 0.0141(11) 0.0575(12) C4 0.0444(12) 0.0386(11) 0.0373(12) 0.0041(9) 0.0051(9) 0.0245(10) C5 0.0574(14) 0.0459(12) 0.0425(13) 0.0090(11) 0.0132(11) 0.0321(11) C6 0.0468(12) 0.0391(11) 0.0359(11) 0.0087(9) 0.0106(10) 0.0218(10) C7 0.0784(18) 0.0431(13) 0.0488(14) -0.0002(12) -0.0076(14) 0.0320(13) C8 0.106(3) 0.0549(18) 0.073(2) 0.0052(16) -0.005(2) 0.0510(19) C9 0.086(2) 0.074(2) 0.083(2) 0.020(2) -0.001(2) 0.0557(19) C10 0.0552(16) 0.0737(19) 0.069(2) 0.0128(17) -0.0114(15) 0.0290(15) C11 0.0492(13) 0.0465(13) 0.0522(16) 0.0084(12) 0.0057(11) 0.0187(11) N2 0.0432(11) 0.0449(11) 0.0349(10) 0.0052(8) 0.0040(8) 0.0228(9) C12 0.0458(11) 0.0373(10) 0.0352(11) 0.0010(10) 0.0007(10) 0.0228(9) O2 0.0443(8) 0.0529(10) 0.0383(9) 0.0052(8) 0.0030(8) 0.0229(8) N3 0.0479(12) 0.0523(12) 0.0355(11) 0.0004(9) -0.0006(9) 0.0197(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 N1 1.441(4) . ? C1 N3 1.456(4) . ? N1 C3 1.341(4) . ? N1 C2 1.473(4) . ? C3 O1 1.226(3) . ? C3 C4 1.548(3) . ? C4 N2 1.474(3) . ? C4 C5 1.523(3) . ? C5 C6 1.509(3) . ? C6 C11 1.385(4) . ? C6 C7 1.397(4) . ? C7 C8 1.388(5) . ? C8 C9 1.376(6) . ? C9 C10 1.374(5) . ? C10 C11 1.388(4) . ? N2 C12 1.355(3) . ? C12 O2 1.257(3) . ? C12 N3 1.344(3) . ? 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 N1 C1 N3 113.8(2) . . ? C3 N1 C1 121.2(2) . . ? C3 N1 C2 118.9(3) . . ? C1 N1 C2 119.8(3) . . ? O1 C3 N1 124.0(3) . . ? O1 C3 C4 121.3(3) . . ? N1 C3 C4 114.7(2) . . ? N2 C4 C5 109.3(2) . . ? N2 C4 C3 111.11(19) . . ? C5 C4 C3 110.8(2) . . ? C6 C5 C4 113.9(2) . . ? C11 C6 C7 118.9(2) . . ? C11 C6 C5 120.9(2) . . ? C7 C6 C5 120.2(2) . . ? C8 C7 C6 120.2(3) . . ? C9 C8 C7 120.1(3) . . ? C10 C9 C8 120.1(3) . . ? C9 C10 C11 120.3(3) . . ? C6 C11 C10 120.4(3) . . ? C12 N2 C4 128.7(2) . . ? O2 C12 N3 119.3(2) . . ? O2 C12 N2 119.7(2) . . ? N3 C12 N2 121.0(2) . . ? C12 N3 C1 125.6(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C1 N1 C3 -66.7(3) . . . . ? N3 C1 N1 C2 109.0(4) . . . . ? C1 N1 C3 O1 176.3(2) . . . . ? C2 N1 C3 O1 0.6(5) . . . . ? C1 N1 C3 C4 -4.2(4) . . . . ? C2 N1 C3 C4 -179.9(3) . . . . ? O1 C3 C4 N2 -112.4(3) . . . . ? N1 C3 C4 N2 68.0(3) . . . . ? O1 C3 C4 C5 9.3(3) . . . . ? N1 C3 C4 C5 -170.2(2) . . . . ? N2 C4 C5 C6 -70.6(3) . . . . ? C3 C4 C5 C6 166.6(2) . . . . ? C4 C5 C6 C11 120.1(3) . . . . ? C4 C5 C6 C7 -61.1(3) . . . . ? C11 C6 C7 C8 -0.5(5) . . . . ? C5 C6 C7 C8 -179.3(3) . . . . ? C6 C7 C8 C9 0.5(6) . . . . ? C7 C8 C9 C10 -0.5(6) . . . . ? C8 C9 C10 C11 0.4(6) . . . . ? C7 C6 C11 C10 0.4(4) . . . . ? C5 C6 C11 C10 179.2(3) . . . . ? C9 C10 C11 C6 -0.4(5) . . . . ? C5 C4 N2 C12 -175.9(2) . . . . ? C3 C4 N2 C12 -53.3(3) . . . . ? C4 N2 C12 O2 179.2(2) . . . . ? C4 N2 C12 N3 -0.5(4) . . . . ? O2 C12 N3 C1 178.5(2) . . . . ? N2 C12 N3 C1 -1.8(4) . . . . ? N1 C1 N3 C12 58.3(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O2 1.019(10) 2.063(17) 3.037(3) 159(3) 3_655 N3 H3 O2 1.025(10) 1.836(14) 2.838(3) 165(3) 4_664 C4 H4 O1 0.98 2.72 3.636(3) 155.9 6_554 C1 H1B O1 0.97 2.53 3.425(3) 152.9 6_554 # Attachment 'compound1c.cif' # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-05-26 at 11:14:05 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.2 # Request file : \wingx\files\archive.dat # CIF files read : import struct # # CCDC ELECTRONIC DATA DEPOSITION FORM (CIF) # # This electronic data deposition form can be used: # # (a) WHEN SUBMITTING A PAPER TO A JOURNAL FOR PUBLICATION or # (b) WHEN SUBMITTING A PRIVATE COMMUNICATION TO THE CCDC # # A comprehensive archive of CIF resources is maintained by the IUCr # at its Chester office. This can be accessed # by anonymous ftp to ftp.iucr.org # or via the WWW at http://www.iucr.org/cif/home.html # If data items in this form are not available or not applicable # then ignore these items # A few items specific to CCDC input are indicated by _ccdc_ # # Submission and help information is provided at the end of this form #------------------------------------------------------------------------- data_import _database_code_depnum_ccdc_archive 'CCDC 603582' _audit_creation_date 2006-05-26T11:14:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety '3 (C21 H23 N3 O3), 0.759(H2 O)' _chemical_formula_sum 'C63 H70.52 N9 O9.76' _chemical_formula_weight 1109.94 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 15.7533(3) _cell_length_b 10.5328(2) _cell_length_c 17.8744(5) _cell_angle_alpha 90 _cell_angle_beta 102.8050(1) _cell_angle_gamma 90 _cell_volume 2892.07(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 27893 _cell_measurement_theta_min 1.17 _cell_measurement_theta_max 24.11 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1179.2 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_unetI/netI 0.0821 _diffrn_reflns_number 27853 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 24.11 _diffrn_reflns_theta_full 24.11 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _reflns_number_total 4816 _reflns_number_gt 2781 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0846P)^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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 4816 _refine_ls_number_parameters 722 _refine_ls_number_restraints 41 _refine_ls_R_factor_all 0.1228 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1443 _refine_ls_wR_factor_gt 0.1205 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.251 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.0494(6) 0.7608(10) 0.0397(4) 0.114(3) Uani 1 1 d . . . H1A H 0.0116 0.7083 0.0018 0.137 Uiso 1 1 calc R . . H1B H 0.0446 0.847 0.02 0.137 Uiso 1 1 calc R . . C2 C 0.1381(5) 0.7190(9) 0.0446(4) 0.085(2) Uani 1 1 d D . . C3 C 0.1694(7) 0.6047(10) 0.0788(5) 0.120(3) Uani 1 1 d D . . H3A H 0.1343 0.5575 0.1039 0.144 Uiso 1 1 calc R . . C4 C 0.2502(7) 0.5597(11) 0.0767(6) 0.127(3) Uani 1 1 d D . . H4 H 0.2674 0.4789 0.095 0.153 Uiso 1 1 calc R . . C5 C 0.3048(7) 0.6342(12) 0.0475(6) 0.132(4) Uani 1 1 d D . . H5 H 0.3614 0.6071 0.0494 0.158 Uiso 1 1 calc R . . C6 C 0.2778(7) 0.7486(13) 0.0154(6) 0.152(4) Uani 1 1 d D . . H6 H 0.3156 0.7993 -0.0048 0.182 Uiso 1 1 calc R . . C7 C 0.1951(7) 0.7879(10) 0.0131(6) 0.130(3) Uani 1 1 d D . . H7 H 0.1765 0.8645 -0.0109 0.156 Uiso 1 1 calc R . . O1 O 0.0155(3) 0.7594(5) 0.1088(2) 0.0844(14) Uani 1 1 d . . . C8 C 0.0461(4) 0.8614(6) 0.1593(3) 0.0637(17) Uani 1 1 d . . . H8 H 0.1099 0.8655 0.1702 0.076 Uiso 1 1 calc R . . C9 C 0.0073(4) 0.9881(7) 0.1320(3) 0.0697(18) Uani 1 1 d . . . H9A H 0.0428 1.032 0.1022 0.084 Uiso 1 1 calc R . . H9B H -0.0511 0.9784 0.1008 0.084 Uiso 1 1 calc R . . N1 N 0.0063(3) 1.0566(5) 0.2028(3) 0.0577(13) Uani 1 1 d . . . C10 C 0.0178(4) 0.9735(5) 0.2692(3) 0.0516(15) Uani 1 1 d . . . H10 H -0.0302 0.9843 0.2954 0.062 Uiso 1 1 calc R . . C11 C 0.0147(4) 0.8424(6) 0.2333(4) 0.0618(17) Uani 1 1 d . . . H11A H -0.0442 0.809 0.2224 0.074 Uiso 1 1 calc R . . H11B H 0.0525 0.784 0.2673 0.074 Uiso 1 1 calc R . . C12 C -0.0059(4) 1.1831(7) 0.2047(4) 0.0571(16) Uani 1 1 d . . . O2 O -0.0218(3) 1.2516(5) 0.1484(2) 0.0745(13) Uani 1 1 d . . . C13 C 0.0078(3) 1.2363(5) 0.2875(3) 0.0514(15) Uani 1 1 d . . . H13 H -0.0316 1.1914 0.3139 0.062 Uiso 1 1 calc R . . N2 N 0.0969(3) 1.2156(5) 0.3302(2) 0.0507(12) Uani 1 1 d . . . H2 H 0.1258 1.2832 0.3463 0.061 Uiso 1 1 calc R . . C14 C 0.1405(4) 1.1052(6) 0.3481(3) 0.0473(14) Uani 1 1 d . . . O3 O 0.2161(3) 1.1028(4) 0.3874(2) 0.0592(10) Uani 1 1 d . . . N3 N 0.1008(3) 0.9935(5) 0.3220(2) 0.0526(12) Uani 1 1 d . . . H3 H 0.1289 0.9258 0.3393 0.063 Uiso 1 1 calc R . . C15 C -0.0141(4) 1.3762(6) 0.2857(3) 0.0567(16) Uani 1 1 d . . . H15A H 0.0276 1.4217 0.2632 0.068 Uiso 1 1 calc R . . H15B H -0.0712 1.3884 0.2525 0.068 Uiso 1 1 calc R . . C16 C -0.0142(3) 1.4338(6) 0.3627(3) 0.0530(15) Uani 1 1 d . . . C17 C 0.0371(3) 1.5378(6) 0.3892(4) 0.0601(16) Uani 1 1 d . . . H17 H 0.0737 1.5709 0.3598 0.072 Uiso 1 1 calc R . . C18 C 0.0348(4) 1.5938(6) 0.4592(4) 0.0670(17) Uani 1 1 d . . . H18 H 0.0691 1.6647 0.4758 0.08 Uiso 1 1 calc R . . C19 C -0.0172(4) 1.5456(7) 0.5034(4) 0.0691(18) Uani 1 1 d . . . H19 H -0.0187 1.5831 0.5502 0.083 Uiso 1 1 calc R . . C20 C -0.0679(4) 1.4405(7) 0.4785(4) 0.0663(16) Uani 1 1 d . . . H20 H -0.1034 1.4071 0.5089 0.08 Uiso 1 1 calc R . . C21 C -0.0668(4) 1.3855(6) 0.4104(3) 0.0588(16) Uani 1 1 d . . . H21 H -0.1013 1.3145 0.3947 0.071 Uiso 1 1 calc R . . C61A C 0.4940(8) 0.4030(11) 0.1656(8) 0.122(3) Uiso 0.528(10) 1 d PD A 1 H61A H 0.4776 0.4244 0.1115 0.146 Uiso 0.528(10) 1 calc PR A 1 H61B H 0.449 0.3482 0.1772 0.146 Uiso 0.528(10) 1 calc PR A 1 C62A C 0.5788(9) 0.3317(13) 0.1809(6) 0.122(3) Uiso 0.528(10) 1 d PD A 1 C63A C 0.5813(11) 0.2015(14) 0.1717(9) 0.122(3) Uiso 0.528(10) 1 d PD A 1 H63A H 0.5296 0.1556 0.1644 0.146 Uiso 0.528(10) 1 calc PR A 1 C67A C 0.6566(8) 0.3939(17) 0.2094(9) 0.122(3) Uiso 0.528(10) 1 d PD A 1 H67A H 0.6564 0.4779 0.2255 0.146 Uiso 0.528(10) 1 calc PR A 1 C64A C 0.6591(9) 0.1366(19) 0.1732(10) 0.122(3) Uiso 0.528(10) 1 d PD A 1 H64A H 0.6602 0.0539 0.1552 0.146 Uiso 0.528(10) 1 calc PR A 1 C66A C 0.7334(11) 0.3321(18) 0.2139(11) 0.122(3) Uiso 0.528(10) 1 d PD A 1 H66A H 0.7855 0.377 0.2243 0.146 Uiso 0.528(10) 1 calc PR A 1 C65A C 0.7336(13) 0.2035(18) 0.2031(11) 0.122(3) Uiso 0.528(10) 1 d PD A 1 H65A H 0.7861 0.1599 0.2164 0.146 Uiso 0.528(10) 1 calc PR A 1 C61B C 0.5753(7) 0.4896(11) 0.1858(9) 0.099(3) Uiso 0.472(10) 1 d PD A 2 H61C H 0.6205 0.5418 0.2168 0.119 Uiso 0.472(10) 1 calc PR A 2 H61D H 0.5675 0.5187 0.1333 0.119 Uiso 0.472(10) 1 calc PR A 2 C62B C 0.6097(8) 0.3550(12) 0.1889(6) 0.099(3) Uiso 0.472(10) 1 d PD A 2 C63B C 0.5620(10) 0.2507(11) 0.1969(9) 0.099(3) Uiso 0.472(10) 1 d PD A 2 H63B H 0.5041 0.2591 0.1999 0.119 Uiso 0.472(10) 1 calc PR A 2 C67B C 0.6956(9) 0.3422(16) 0.1774(9) 0.099(3) Uiso 0.472(10) 1 d PD A 2 H67B H 0.7243 0.414 0.1654 0.119 Uiso 0.472(10) 1 calc PR A 2 C64B C 0.6002(9) 0.1311(15) 0.2007(9) 0.099(3) Uiso 0.472(10) 1 d PD A 2 H64B H 0.5688 0.0569 0.2028 0.119 Uiso 0.472(10) 1 calc PR A 2 C66B C 0.7378(12) 0.2275(13) 0.1833(10) 0.099(3) Uiso 0.472(10) 1 d PD A 2 H66B H 0.794 0.2169 0.176 0.119 Uiso 0.472(10) 1 calc PR A 2 C65B C 0.6878(10) 0.1301(18) 0.2011(10) 0.099(3) Uiso 0.472(10) 1 d PD A 2 H65B H 0.7167 0.0538 0.2153 0.119 Uiso 0.472(10) 1 calc PR A 2 O61 O 0.4980(3) 0.5152(6) 0.2093(3) 0.1003(16) Uani 1 1 d D . . C68 C 0.4906(4) 0.5023(7) 0.2865(4) 0.0732(19) Uani 1 1 d . A . H68 H 0.5224 0.4283 0.3116 0.088 Uiso 1 1 calc R . . C69 C 0.5197(4) 0.6242(7) 0.3289(4) 0.0734(19) Uani 1 1 d . . . H69A H 0.5345 0.6105 0.3839 0.088 Uiso 1 1 calc R A . H69B H 0.5695 0.6602 0.313 0.088 Uiso 1 1 calc R . . N61 N 0.4430(3) 0.7062(5) 0.3066(3) 0.0622(13) Uani 1 1 d . A . C70 C 0.3637(4) 0.6326(6) 0.2728(3) 0.0568(16) Uani 1 1 d . . . H70 H 0.3456 0.6499 0.2177 0.068 Uiso 1 1 calc R A . C71 C 0.3943(4) 0.4962(6) 0.2859(4) 0.0730(19) Uani 1 1 d . A . H71A H 0.385 0.4647 0.3345 0.088 Uiso 1 1 calc R . . H71B H 0.3638 0.4416 0.245 0.088 Uiso 1 1 calc R . . C72 C 0.4466(4) 0.8338(7) 0.3011(3) 0.0594(16) Uani 1 1 d . . . O62 O 0.5157(3) 0.8914(4) 0.3239(2) 0.0700(12) Uani 1 1 d . A . C73 C 0.3612(4) 0.8968(6) 0.2642(3) 0.0576(16) Uani 1 1 d . A . H73 H 0.3393 0.8588 0.2135 0.069 Uiso 1 1 calc R . . N62 N 0.2958(3) 0.8795(5) 0.3102(3) 0.0551(13) Uani 1 1 d . . . H62 H 0.2758 0.9478 0.3262 0.066 Uiso 1 1 calc R A . C74 C 0.2627(4) 0.7688(7) 0.3307(3) 0.0538(14) Uani 1 1 d . A . O63 O 0.2053(2) 0.7704(4) 0.3689(2) 0.0592(10) Uani 1 1 d . . . N63 N 0.2919(3) 0.6575(5) 0.3101(3) 0.0611(14) Uani 1 1 d . A . H63 H 0.2644 0.5915 0.3204 0.073 Uiso 1 1 calc R . . C75 C 0.3757(4) 1.0396(6) 0.2540(4) 0.0706(18) Uani 1 1 d . . . H75A H 0.3857 1.0799 0.304 0.085 Uiso 1 1 calc R A . H75B H 0.428 1.0504 0.2346 0.085 Uiso 1 1 calc R . . C76 C 0.3033(4) 1.1067(7) 0.2019(4) 0.0661(17) Uani 1 1 d . A . C77 C 0.2633(5) 1.2105(8) 0.2279(5) 0.085(2) Uani 1 1 d . . . H77 H 0.2808 1.2351 0.279 0.102 Uiso 1 1 calc R A . C78 C 0.1992(5) 1.2769(10) 0.1802(7) 0.108(3) Uani 1 1 d . A . H78 H 0.174 1.3468 0.1984 0.13 Uiso 1 1 calc R . . C79 C 0.1726(5) 1.2411(11) 0.1067(7) 0.108(3) Uani 1 1 d . . . H79 H 0.129 1.2874 0.0745 0.13 Uiso 1 1 calc R A . C80 C 0.2073(7) 1.1394(11) 0.0781(6) 0.121(3) Uani 1 1 d . A . H80 H 0.1872 1.1143 0.0274 0.146 Uiso 1 1 calc R . . C81 C 0.2762(6) 1.0713(9) 0.1282(5) 0.102(3) Uani 1 1 d . . . H81 H 0.3021 1.0024 0.1095 0.122 Uiso 1 1 calc R A . C31 C 0.2451(4) 0.2251(10) 0.7934(4) 0.099(3) Uani 1 1 d . . . H31A H 0.2167 0.1485 0.8054 0.118 Uiso 1 1 calc R . . H31B H 0.2042 0.2948 0.7898 0.118 Uiso 1 1 calc R . . C32 C 0.3214(5) 0.2508(9) 0.8541(4) 0.096(2) Uani 1 1 d D . . C33 C 0.3981(5) 0.2959(9) 0.8420(5) 0.109(3) Uani 1 1 d D . . H33A H 0.4021 0.3148 0.792 0.131 Uiso 1 1 calc R . . C34 C 0.4699(6) 0.3148(12) 0.9003(5) 0.140(4) Uani 1 1 d D . . H34 H 0.521 0.3461 0.8893 0.168 Uiso 1 1 calc R . . C35 C 0.4669(7) 0.2880(18) 0.9744(6) 0.207(8) Uani 1 1 d D . . H35 H 0.5143 0.3011 1.015 0.248 Uiso 1 1 calc R . . C36 C 0.3893(8) 0.240(2) 0.9849(6) 0.266(12) Uani 1 1 d D . . H36 H 0.3848 0.2222 1.0348 0.319 Uiso 1 1 calc R . . C37 C 0.3167(7) 0.2175(19) 0.9257(5) 0.220(9) Uani 1 1 d D . . H37 H 0.2667 0.1805 0.9355 0.264 Uiso 1 1 calc R . . O31 O 0.2699(2) 0.2096(4) 0.7208(2) 0.0689(12) Uani 1 1 d . . . C38 C 0.1991(4) 0.1912(6) 0.6565(4) 0.0669(17) Uani 1 1 d . . . H38 H 0.1624 0.1191 0.6636 0.08 Uiso 1 1 calc R . . C39 C 0.1469(4) 0.3115(6) 0.6354(4) 0.0613(17) Uani 1 1 d . . . H39A H 0.0918 0.2942 0.6002 0.074 Uiso 1 1 calc R . . H39B H 0.1361 0.3536 0.6806 0.074 Uiso 1 1 calc R . . N31 N 0.2041(3) 0.3878(5) 0.5986(3) 0.0512(12) Uani 1 1 d . . . C40 C 0.2652(3) 0.3075(5) 0.5690(3) 0.0513(15) Uani 1 1 d . . . H40 H 0.3251 0.3259 0.5961 0.062 Uiso 1 1 calc R . . C41 C 0.2400(4) 0.1734(6) 0.5878(3) 0.0620(17) Uani 1 1 d . . . H41A H 0.1986 0.1367 0.5449 0.074 Uiso 1 1 calc R . . H41B H 0.2908 0.119 0.6006 0.074 Uiso 1 1 calc R . . C42 C 0.2113(3) 0.5141(6) 0.6053(3) 0.0498(15) Uani 1 1 d . . . O32 O 0.1642(2) 0.5779(4) 0.6368(2) 0.0621(11) Uani 1 1 d . . . C43 C 0.2814(3) 0.5688(5) 0.5693(3) 0.0475(14) Uani 1 1 d . . . H43 H 0.3364 0.5258 0.5915 0.057 Uiso 1 1 calc R . . N32 N 0.2607(3) 0.5471(5) 0.4854(3) 0.0525(12) Uani 1 1 d . . . H32 H 0.2561 0.6143 0.4574 0.063 Uiso 1 1 calc R . . C44 C 0.2479(3) 0.4355(6) 0.4469(4) 0.0501(14) Uani 1 1 d . . . O33 O 0.2283(2) 0.4329(4) 0.3755(2) 0.0539(10) Uani 1 1 d . . . N33 N 0.2561(3) 0.3239(5) 0.4870(3) 0.0543(12) Uani 1 1 d . . . H33 H 0.2558 0.2556 0.4606 0.065 Uiso 1 1 calc R . . C45 C 0.2939(3) 0.7121(6) 0.5847(3) 0.0570(15) Uani 1 1 d . . . H45A H 0.241 0.7556 0.5596 0.068 Uiso 1 1 calc R . . H45B H 0.3021 0.7266 0.6395 0.068 Uiso 1 1 calc R . . C46 C 0.3695(3) 0.7704(6) 0.5579(3) 0.0515(14) Uani 1 1 d . . . C47 C 0.3577(4) 0.8753(6) 0.5117(3) 0.0600(16) Uani 1 1 d . . . H47 H 0.3023 0.9099 0.496 0.072 Uiso 1 1 calc R . . C48 C 0.4268(5) 0.9308(7) 0.4880(4) 0.0729(18) Uani 1 1 d . . . H48 H 0.4176 1.0027 0.4571 0.087 Uiso 1 1 calc R . . C49 C 0.5088(5) 0.8803(8) 0.5099(4) 0.077(2) Uani 1 1 d . . . H49 H 0.5554 0.9176 0.4941 0.092 Uiso 1 1 calc R . . C50 C 0.5214(4) 0.7731(8) 0.5558(4) 0.0748(19) Uani 1 1 d . . . H50 H 0.5767 0.7379 0.5709 0.09 Uiso 1 1 calc R . . C51 C 0.4530(4) 0.7189(6) 0.5788(3) 0.0630(16) Uani 1 1 d . . . H51 H 0.4621 0.6462 0.609 0.076 Uiso 1 1 calc R . . O91 O -0.0848(6) 0.5236(9) 0.1047(5) 0.152(5) Uani 0.759(15) 1 d P . . H91A H -0.0485 0.4559 0.122 0.183 Uiso 0.759(15) 1 d P . . H91B H -0.0443 0.6056 0.1002 0.183 Uiso 0.759(15) 1 d P . . 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 C1 0.148(8) 0.104(7) 0.086(5) -0.031(5) 0.015(5) 0.008(7) C2 0.069(5) 0.090(7) 0.091(5) -0.042(5) 0.006(4) 0.009(5) C3 0.120(8) 0.115(8) 0.131(7) 0.018(7) 0.042(6) 0.004(7) C4 0.111(7) 0.121(9) 0.149(8) 0.021(7) 0.027(7) 0.018(7) C5 0.116(8) 0.140(11) 0.135(8) 0.009(8) 0.020(7) 0.016(8) C6 0.131(9) 0.178(14) 0.149(9) 0.046(10) 0.038(7) -0.019(9) C7 0.109(7) 0.116(9) 0.151(8) 0.025(7) -0.001(7) -0.007(8) O1 0.106(3) 0.086(4) 0.064(3) -0.028(3) 0.026(2) -0.024(3) C8 0.071(4) 0.053(5) 0.068(4) -0.022(4) 0.015(3) -0.006(3) C9 0.087(4) 0.069(5) 0.053(4) -0.011(4) 0.017(3) -0.007(4) N1 0.068(3) 0.055(4) 0.051(3) -0.005(3) 0.014(2) -0.006(3) C10 0.057(4) 0.042(4) 0.056(4) 0.001(3) 0.012(3) -0.009(3) C11 0.059(4) 0.056(4) 0.072(4) -0.007(3) 0.016(3) -0.014(3) C12 0.051(4) 0.058(5) 0.063(5) -0.003(4) 0.014(3) -0.004(3) O2 0.098(3) 0.070(3) 0.052(2) 0.019(3) 0.010(2) 0.009(3) C13 0.053(3) 0.051(4) 0.048(3) -0.002(3) 0.006(3) -0.002(3) N2 0.052(3) 0.043(3) 0.055(3) -0.006(2) 0.006(2) -0.002(2) C14 0.053(4) 0.042(4) 0.048(3) 0.001(3) 0.015(3) 0.003(4) O3 0.054(3) 0.052(3) 0.067(2) -0.001(2) 0.003(2) 0.003(2) N3 0.057(3) 0.044(3) 0.056(3) -0.002(2) 0.013(2) -0.004(2) C15 0.058(4) 0.055(4) 0.058(4) 0.011(3) 0.014(3) 0.007(3) C16 0.053(3) 0.041(4) 0.062(4) -0.001(3) 0.006(3) 0.012(3) C17 0.050(3) 0.050(4) 0.080(4) -0.002(4) 0.014(3) 0.007(3) C18 0.058(4) 0.053(4) 0.092(5) -0.019(4) 0.021(4) 0.006(3) C19 0.067(4) 0.074(5) 0.068(4) -0.007(4) 0.017(4) 0.009(4) C20 0.074(4) 0.057(4) 0.074(4) -0.001(4) 0.030(3) 0.006(4) C21 0.060(4) 0.048(4) 0.069(4) 0.000(4) 0.015(3) -0.006(3) O61 0.085(3) 0.111(4) 0.115(4) 0.003(4) 0.044(3) 0.014(3) C68 0.069(4) 0.068(5) 0.088(5) 0.017(4) 0.029(4) 0.021(4) C69 0.064(4) 0.076(5) 0.082(4) 0.006(4) 0.019(3) 0.008(4) N61 0.049(3) 0.053(4) 0.083(4) -0.002(3) 0.013(3) 0.002(3) C70 0.056(4) 0.050(4) 0.070(4) -0.002(3) 0.026(3) 0.003(3) C71 0.076(4) 0.049(4) 0.099(5) 0.004(4) 0.032(4) 0.003(4) C72 0.054(4) 0.067(5) 0.061(4) -0.005(4) 0.021(3) -0.010(4) O62 0.053(3) 0.070(3) 0.087(3) -0.004(2) 0.015(2) -0.007(2) C73 0.052(4) 0.056(4) 0.063(4) 0.001(3) 0.008(3) -0.011(3) N62 0.051(3) 0.042(3) 0.075(3) 0.004(3) 0.021(2) -0.001(2) C74 0.051(3) 0.048(4) 0.061(3) -0.004(3) 0.007(3) 0.000(4) O63 0.056(2) 0.051(3) 0.076(3) 0.004(2) 0.026(2) -0.002(2) N63 0.060(3) 0.049(4) 0.076(3) 0.002(3) 0.018(3) -0.007(3) C75 0.067(4) 0.051(4) 0.094(5) 0.010(4) 0.019(4) -0.008(4) C76 0.075(4) 0.052(4) 0.073(5) 0.010(4) 0.020(4) -0.011(4) C77 0.082(5) 0.064(5) 0.117(6) 0.025(5) 0.042(5) -0.003(4) C78 0.091(6) 0.095(7) 0.143(8) 0.036(7) 0.036(6) -0.003(6) C79 0.084(6) 0.107(9) 0.125(8) 0.038(7) 0.003(6) -0.008(6) C80 0.154(9) 0.113(9) 0.092(6) 0.010(7) 0.018(6) -0.004(7) C81 0.133(7) 0.086(6) 0.082(6) 0.003(5) 0.014(5) 0.005(6) C31 0.080(5) 0.140(8) 0.079(5) 0.003(5) 0.026(4) -0.005(5) C32 0.081(5) 0.135(8) 0.078(5) -0.003(5) 0.029(4) 0.008(5) C33 0.106(6) 0.126(9) 0.089(6) -0.001(5) 0.012(5) -0.011(6) C34 0.101(7) 0.193(12) 0.122(8) -0.023(8) 0.016(6) -0.024(7) C35 0.133(10) 0.40(3) 0.086(8) -0.018(11) 0.015(6) -0.021(14) C36 0.164(11) 0.54(4) 0.097(8) 0.055(15) 0.034(9) -0.016(19) C37 0.127(8) 0.45(3) 0.082(6) 0.029(11) 0.018(6) -0.054(13) O31 0.063(3) 0.075(3) 0.070(3) 0.006(2) 0.020(2) 0.006(2) C38 0.061(4) 0.054(4) 0.086(5) 0.008(4) 0.019(4) -0.008(3) C39 0.050(3) 0.058(4) 0.080(4) 0.007(3) 0.021(3) -0.006(3) N31 0.045(3) 0.044(3) 0.069(3) 0.001(3) 0.021(2) 0.002(2) C40 0.041(3) 0.047(4) 0.065(4) -0.002(3) 0.011(3) -0.006(3) C41 0.062(4) 0.050(4) 0.074(4) 0.000(3) 0.015(3) -0.003(3) C42 0.046(3) 0.054(5) 0.051(3) -0.003(3) 0.015(3) 0.003(3) O32 0.057(2) 0.059(3) 0.073(3) -0.005(2) 0.022(2) 0.003(2) C43 0.045(3) 0.043(4) 0.056(4) -0.004(3) 0.014(3) -0.001(3) N32 0.059(3) 0.037(3) 0.065(3) -0.004(3) 0.021(2) -0.007(2) C44 0.039(3) 0.047(4) 0.067(4) 0.001(4) 0.017(3) 0.002(3) O33 0.061(2) 0.052(2) 0.049(2) -0.005(2) 0.0122(18) -0.006(2) N33 0.059(3) 0.046(3) 0.058(3) -0.004(3) 0.013(2) 0.003(2) C45 0.054(3) 0.044(4) 0.075(4) -0.014(3) 0.018(3) -0.005(3) C46 0.055(4) 0.039(3) 0.061(3) -0.008(3) 0.013(3) -0.001(3) C47 0.058(4) 0.049(4) 0.069(4) 0.002(4) 0.006(3) 0.001(3) C48 0.080(5) 0.065(4) 0.071(4) 0.003(4) 0.010(4) -0.023(4) C49 0.075(5) 0.078(6) 0.081(5) -0.007(5) 0.023(4) -0.029(4) C50 0.054(4) 0.066(5) 0.106(5) -0.008(5) 0.020(3) -0.007(4) C51 0.056(4) 0.043(4) 0.091(4) 0.007(3) 0.018(3) -0.006(3) O91 0.180(8) 0.122(8) 0.120(7) 0.038(6) -0.039(5) -0.036(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C2 1.449(10) . ? C1 O1 1.451(9) . ? C2 C7 1.369(8) . ? C2 C3 1.391(8) . ? C3 C4 1.367(8) . ? C4 C5 1.352(8) . ? C5 C6 1.361(9) . ? C6 C7 1.359(8) . ? O1 C8 1.417(7) . ? C8 C9 1.504(9) . ? C8 C11 1.525(8) . ? C9 N1 1.460(7) . ? N1 C12 1.348(8) . ? N1 C10 1.454(7) . ? C10 N3 1.449(7) . ? C10 C11 1.519(8) . ? C12 O2 1.219(7) . ? C12 C13 1.552(8) . ? C13 N2 1.458(6) . ? C13 C15 1.512(8) . ? N2 C14 1.353(7) . ? C14 O3 1.241(6) . ? C14 N3 1.365(7) . ? C15 C16 1.505(8) . ? C16 C17 1.382(8) . ? C16 C21 1.408(8) . ? C17 C18 1.391(8) . ? C18 C19 1.358(8) . ? C19 C20 1.380(9) . ? C20 C21 1.352(8) . ? C61A O61 1.411(9) . ? C61A C62A 1.504(9) . ? C62A C63A 1.383(10) . ? C62A C67A 1.384(10) . ? C63A C64A 1.399(10) . ? C67A C66A 1.360(10) . ? C64A C65A 1.372(10) . ? C66A C65A 1.369(10) . ? C61B O61 1.398(8) . ? C61B C62B 1.514(9) . ? C62B C63B 1.356(9) . ? C62B C67B 1.420(10) . ? C63B C64B 1.391(10) . ? C67B C66B 1.371(10) . ? C64B C65B 1.378(10) . ? C66B C65B 1.373(10) . ? O61 C68 1.417(7) . ? C68 C69 1.509(10) . ? C68 C71 1.516(8) . ? C69 N61 1.466(8) . ? N61 C72 1.349(8) . ? N61 C70 1.481(7) . ? C70 N63 1.459(7) . ? C70 C71 1.517(9) . ? C72 O62 1.234(7) . ? C72 C73 1.514(9) . ? C73 N62 1.466(7) . ? C73 C75 1.539(9) . ? N62 C74 1.359(8) . ? C74 O63 1.249(6) . ? C74 N63 1.340(8) . ? C75 C76 1.482(9) . ? C76 C81 1.346(10) . ? C76 C77 1.392(10) . ? C77 C78 1.362(10) . ? C78 C79 1.341(12) . ? C79 C80 1.354(13) . ? C80 C81 1.436(12) . ? C31 O31 1.445(7) . ? C31 C32 1.455(10) . ? C32 C37 1.345(8) . ? C32 C33 1.360(7) . ? C33 C34 1.372(8) . ? C34 C35 1.365(8) . ? C35 C36 1.371(9) . ? C36 C37 1.396(9) . ? O31 C38 1.427(7) . ? C38 C39 1.512(9) . ? C38 C41 1.518(8) . ? C39 N31 1.466(7) . ? N31 C42 1.338(7) . ? N31 C40 1.466(7) . ? C40 N33 1.450(7) . ? C40 C41 1.525(8) . ? C42 O32 1.225(6) . ? C42 C43 1.511(7) . ? C43 N32 1.480(7) . ? C43 C45 1.538(8) . ? N32 C44 1.354(7) . ? C44 O33 1.246(6) . ? C44 N33 1.369(8) . ? C45 C46 1.511(7) . ? C46 C47 1.367(8) . ? C46 C51 1.394(8) . ? C47 C48 1.382(8) . ? C48 C49 1.372(10) . ? C49 C50 1.384(10) . ? C50 C51 1.361(8) . ? 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 C1 O1 118.6(7) . . ? C7 C2 C3 116.0(8) . . ? C7 C2 C1 121.7(9) . . ? C3 C2 C1 122.2(9) . . ? C4 C3 C2 122.0(9) . . ? C5 C4 C3 119.1(10) . . ? C4 C5 C6 120.7(10) . . ? C7 C6 C5 119.4(10) . . ? C6 C7 C2 122.6(9) . . ? C8 O1 C1 113.4(5) . . ? O1 C8 C9 114.2(5) . . ? O1 C8 C11 108.8(5) . . ? C9 C8 C11 102.2(5) . . ? N1 C9 C8 103.8(5) . . ? C12 N1 C10 124.5(5) . . ? C12 N1 C9 122.7(5) . . ? C10 N1 C9 112.8(5) . . ? N3 C10 N1 112.1(4) . . ? N3 C10 C11 110.3(5) . . ? N1 C10 C11 102.5(4) . . ? C10 C11 C8 105.1(5) . . ? O2 C12 N1 124.7(6) . . ? O2 C12 C13 122.2(6) . . ? N1 C12 C13 113.0(6) . . ? N2 C13 C15 110.2(5) . . ? N2 C13 C12 111.0(4) . . ? C15 C13 C12 110.4(5) . . ? C14 N2 C13 129.2(5) . . ? O3 C14 N2 121.6(5) . . ? O3 C14 N3 119.1(5) . . ? N2 C14 N3 119.3(5) . . ? C14 N3 C10 128.8(5) . . ? C16 C15 C13 114.8(5) . . ? C17 C16 C21 117.2(5) . . ? C17 C16 C15 121.0(5) . . ? C21 C16 C15 121.8(5) . . ? C16 C17 C18 121.0(6) . . ? C19 C18 C17 120.3(6) . . ? C18 C19 C20 119.6(6) . . ? C21 C20 C19 120.8(6) . . ? C20 C21 C16 121.1(6) . . ? O61 C61A C62A 112.9(8) . . ? C63A C62A C67A 117.9(14) . . ? C63A C62A C61A 121.4(10) . . ? C67A C62A C61A 120.6(10) . . ? C62A C63A C64A 122.0(17) . . ? C66A C67A C62A 119.9(16) . . ? C65A C64A C63A 115.3(19) . . ? C67A C66A C65A 120(2) . . ? C66A C65A C64A 122(2) . . ? O61 C61B C62B 119.9(9) . . ? C63B C62B C67B 120.4(13) . . ? C63B C62B C61B 124.0(10) . . ? C67B C62B C61B 115.4(9) . . ? C62B C63B C64B 119.7(15) . . ? C66B C67B C62B 122.3(16) . . ? C65B C64B C63B 115.4(16) . . ? C67B C66B C65B 112.6(17) . . ? C66B C65B C64B 128.1(18) . . ? C61B O61 C61A 66.9(8) . . ? C61B O61 C68 122.6(8) . . ? C61A O61 C68 117.0(8) . . ? O61 C68 C69 109.0(6) . . ? O61 C68 C71 107.2(5) . . ? C69 C68 C71 103.4(5) . . ? N61 C69 C68 103.0(5) . . ? C72 N61 C69 124.1(5) . . ? C72 N61 C70 122.5(5) . . ? C69 N61 C70 111.8(5) . . ? N63 C70 N61 112.8(5) . . ? N63 C70 C71 110.6(5) . . ? N61 C70 C71 102.9(5) . . ? C68 C71 C70 104.1(5) . . ? O62 C72 N61 120.9(6) . . ? O62 C72 C73 124.2(6) . . ? N61 C72 C73 114.9(6) . . ? N62 C73 C72 111.6(5) . . ? N62 C73 C75 109.2(5) . . ? C72 C73 C75 109.8(5) . . ? C74 N62 C73 128.1(5) . . ? O63 C74 N63 119.7(6) . . ? O63 C74 N62 120.2(6) . . ? N63 C74 N62 120.1(5) . . ? C74 N63 C70 129.1(5) . . ? C76 C75 C73 115.3(5) . . ? C81 C76 C77 118.5(7) . . ? C81 C76 C75 121.1(7) . . ? C77 C76 C75 120.4(7) . . ? C78 C77 C76 121.4(8) . . ? C79 C78 C77 119.9(10) . . ? C78 C79 C80 121.8(10) . . ? C79 C80 C81 118.2(9) . . ? C76 C81 C80 120.3(9) . . ? O31 C31 C32 110.4(6) . . ? C37 C32 C33 118.8(8) . . ? C37 C32 C31 116.8(8) . . ? C33 C32 C31 124.2(7) . . ? C32 C33 C34 122.8(8) . . ? C35 C34 C33 120.5(9) . . ? C34 C35 C36 115.6(9) . . ? C35 C36 C37 124.4(10) . . ? C32 C37 C36 117.9(10) . . ? C38 O31 C31 114.9(4) . . ? O31 C38 C39 111.8(5) . . ? O31 C38 C41 105.8(4) . . ? C39 C38 C41 101.9(5) . . ? N31 C39 C38 102.5(4) . . ? C42 N31 C39 123.5(5) . . ? C42 N31 C40 123.8(5) . . ? C39 N31 C40 111.3(5) . . ? N33 C40 N31 111.7(4) . . ? N33 C40 C41 111.2(5) . . ? N31 C40 C41 103.3(4) . . ? C38 C41 C40 104.0(5) . . ? O32 C42 N31 122.6(5) . . ? O32 C42 C43 124.0(6) . . ? N31 C42 C43 113.4(5) . . ? N32 C43 C42 110.8(4) . . ? N32 C43 C45 108.9(5) . . ? C42 C43 C45 112.0(5) . . ? C44 N32 C43 128.6(5) . . ? O33 C44 N32 121.0(6) . . ? O33 C44 N33 119.4(6) . . ? N32 C44 N33 119.6(5) . . ? C44 N33 C40 127.5(5) . . ? C46 C45 C43 114.8(5) . . ? C47 C46 C51 118.1(6) . . ? C47 C46 C45 120.6(5) . . ? C51 C46 C45 121.4(6) . . ? C46 C47 C48 121.0(6) . . ? C49 C48 C47 120.3(7) . . ? C48 C49 C50 119.2(6) . . ? C51 C50 C49 120.1(6) . . ? C50 C51 C46 121.3(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C7 -132.4(9) . . . . ? O1 C1 C2 C3 50.1(11) . . . . ? C7 C2 C3 C4 -4.2(14) . . . . ? C1 C2 C3 C4 173.4(8) . . . . ? C2 C3 C4 C5 7.0(16) . . . . ? C3 C4 C5 C6 -4.9(17) . . . . ? C4 C5 C6 C7 0.2(17) . . . . ? C5 C6 C7 C2 2.6(17) . . . . ? C3 C2 C7 C6 -0.6(14) . . . . ? C1 C2 C7 C6 -178.3(9) . . . . ? C2 C1 O1 C8 76.7(9) . . . . ? C1 O1 C8 C9 72.8(7) . . . . ? C1 O1 C8 C11 -173.8(6) . . . . ? O1 C8 C9 N1 149.2(5) . . . . ? C11 C8 C9 N1 31.9(6) . . . . ? C8 C9 N1 C12 165.2(5) . . . . ? C8 C9 N1 C10 -16.1(7) . . . . ? C12 N1 C10 N3 -70.1(7) . . . . ? C9 N1 C10 N3 111.2(5) . . . . ? C12 N1 C10 C11 171.7(5) . . . . ? C9 N1 C10 C11 -7.0(6) . . . . ? N3 C10 C11 C8 -92.2(5) . . . . ? N1 C10 C11 C8 27.2(6) . . . . ? O1 C8 C11 C10 -158.2(5) . . . . ? C9 C8 C11 C10 -37.1(6) . . . . ? C10 N1 C12 O2 -174.4(5) . . . . ? C9 N1 C12 O2 4.2(9) . . . . ? C10 N1 C12 C13 9.0(8) . . . . ? C9 N1 C12 C13 -172.4(5) . . . . ? O2 C12 C13 N2 -114.5(6) . . . . ? N1 C12 C13 N2 62.2(6) . . . . ? O2 C12 C13 C15 8.1(7) . . . . ? N1 C12 C13 C15 -175.2(5) . . . . ? C15 C13 N2 C14 176.8(5) . . . . ? C12 C13 N2 C14 -60.5(7) . . . . ? C13 N2 C14 O3 -177.5(4) . . . . ? C13 N2 C14 N3 2.8(8) . . . . ? O3 C14 N3 C10 -172.8(5) . . . . ? N2 C14 N3 C10 6.9(8) . . . . ? N1 C10 N3 C14 44.9(7) . . . . ? C11 C10 N3 C14 158.4(5) . . . . ? N2 C13 C15 C16 -64.4(6) . . . . ? C12 C13 C15 C16 172.5(4) . . . . ? C13 C15 C16 C17 124.1(6) . . . . ? C13 C15 C16 C21 -56.6(7) . . . . ? C21 C16 C17 C18 -1.6(8) . . . . ? C15 C16 C17 C18 177.8(5) . . . . ? C16 C17 C18 C19 1.1(9) . . . . ? C17 C18 C19 C20 0.0(9) . . . . ? C18 C19 C20 C21 -0.4(9) . . . . ? C19 C20 C21 C16 -0.3(9) . . . . ? C17 C16 C21 C20 1.2(8) . . . . ? C15 C16 C21 C20 -178.2(5) . . . . ? O61 C61A C62A C63A 152.1(13) . . . . ? O61 C61A C62A C67A -23.6(14) . . . . ? C67A C62A C63A C64A -15(2) . . . . ? C61A C62A C63A C64A 169.2(13) . . . . ? C63A C62A C67A C66A 12(2) . . . . ? C61A C62A C67A C66A -171.8(13) . . . . ? C62A C63A C64A C65A 16(2) . . . . ? C62A C67A C66A C65A -11(3) . . . . ? C67A C66A C65A C64A 13(3) . . . . ? C63A C64A C65A C66A -15(3) . . . . ? O61 C61B C62B C63B 15.1(14) . . . . ? O61 C61B C62B C67B -169.0(13) . . . . ? C67B C62B C63B C64B 5.7(19) . . . . ? C61B C62B C63B C64B -178.7(13) . . . . ? C63B C62B C67B C66B -8(2) . . . . ? C61B C62B C67B C66B 175.8(14) . . . . ? C62B C63B C64B C65B 4(2) . . . . ? C62B C67B C66B C65B 0(2) . . . . ? C67B C66B C65B C64B 12(3) . . . . ? C63B C64B C65B C66B -14(3) . . . . ? C62B C61B O61 C61A -41.5(10) . . . . ? C62B C61B O61 C68 66.8(13) . . . . ? C62A C61A O61 C61B 35.8(9) . . . . ? C62A C61A O61 C68 -80.3(10) . . . . ? C61B O61 C68 C69 86.5(9) . . . . ? C61A O61 C68 C69 165.2(7) . . . . ? C61B O61 C68 C71 -162.2(8) . . . . ? C61A O61 C68 C71 -83.5(8) . . . . ? O61 C68 C69 N61 80.4(6) . . . . ? C71 C68 C69 N61 -33.4(6) . . . . ? C68 C69 N61 C72 -149.8(6) . . . . ? C68 C69 N61 C70 16.2(6) . . . . ? C72 N61 C70 N63 -66.9(7) . . . . ? C69 N61 C70 N63 126.8(5) . . . . ? C72 N61 C70 C71 173.9(6) . . . . ? C69 N61 C70 C71 7.7(6) . . . . ? O61 C68 C71 C70 -76.1(7) . . . . ? C69 C68 C71 C70 39.0(7) . . . . ? N63 C70 C71 C68 -149.2(5) . . . . ? N61 C70 C71 C68 -28.4(6) . . . . ? C69 N61 C72 O62 -8.9(9) . . . . ? C70 N61 C72 O62 -173.5(5) . . . . ? C69 N61 C72 C73 169.9(5) . . . . ? C70 N61 C72 C73 5.4(8) . . . . ? O62 C72 C73 N62 -116.9(6) . . . . ? N61 C72 C73 N62 64.3(7) . . . . ? O62 C72 C73 C75 4.3(8) . . . . ? N61 C72 C73 C75 -174.5(5) . . . . ? C72 C73 N62 C74 -60.2(7) . . . . ? C75 C73 N62 C74 178.2(5) . . . . ? C73 N62 C74 O63 -178.3(5) . . . . ? C73 N62 C74 N63 1.9(8) . . . . ? O63 C74 N63 C70 -173.2(5) . . . . ? N62 C74 N63 C70 6.6(9) . . . . ? N61 C70 N63 C74 45.0(8) . . . . ? C71 C70 N63 C74 159.6(6) . . . . ? N62 C73 C75 C76 -71.7(7) . . . . ? C72 C73 C75 C76 165.6(5) . . . . ? C73 C75 C76 C81 -59.0(9) . . . . ? C73 C75 C76 C77 122.9(7) . . . . ? C81 C76 C77 C78 -1.0(10) . . . . ? C75 C76 C77 C78 177.1(6) . . . . ? C76 C77 C78 C79 1.0(11) . . . . ? C77 C78 C79 C80 0.4(13) . . . . ? C78 C79 C80 C81 -1.7(14) . . . . ? C77 C76 C81 C80 -0.3(11) . . . . ? C75 C76 C81 C80 -178.5(7) . . . . ? C79 C80 C81 C76 1.6(13) . . . . ? O31 C31 C32 C37 -153.9(11) . . . . ? O31 C31 C32 C33 20.6(13) . . . . ? C37 C32 C33 C34 -3.2(17) . . . . ? C31 C32 C33 C34 -177.6(10) . . . . ? C32 C33 C34 C35 0.2(19) . . . . ? C33 C34 C35 C36 1(2) . . . . ? C34 C35 C36 C37 1(3) . . . . ? C33 C32 C37 C36 5(2) . . . . ? C31 C32 C37 C36 179.6(15) . . . . ? C35 C36 C37 C32 -4(3) . . . . ? C32 C31 O31 C38 -176.6(7) . . . . ? C31 O31 C38 C39 71.4(7) . . . . ? C31 O31 C38 C41 -178.4(6) . . . . ? O31 C38 C39 N31 74.5(6) . . . . ? C41 C38 C39 N31 -38.1(6) . . . . ? C38 C39 N31 C42 -144.3(5) . . . . ? C38 C39 N31 C40 23.1(6) . . . . ? C42 N31 C40 N33 -71.3(7) . . . . ? C39 N31 C40 N33 121.3(5) . . . . ? C42 N31 C40 C41 169.1(5) . . . . ? C39 N31 C40 C41 1.8(6) . . . . ? O31 C38 C41 C40 -77.0(6) . . . . ? C39 C38 C41 C40 40.0(6) . . . . ? N33 C40 C41 C38 -145.9(5) . . . . ? N31 C40 C41 C38 -25.9(6) . . . . ? C39 N31 C42 O32 -7.2(9) . . . . ? C40 N31 C42 O32 -173.0(5) . . . . ? C39 N31 C42 C43 173.7(5) . . . . ? C40 N31 C42 C43 7.9(8) . . . . ? O32 C42 C43 N32 -115.3(6) . . . . ? N31 C42 C43 N32 63.7(6) . . . . ? O32 C42 C43 C45 6.4(7) . . . . ? N31 C42 C43 C45 -174.5(5) . . . . ? C42 C43 N32 C44 -59.0(7) . . . . ? C45 C43 N32 C44 177.4(5) . . . . ? C43 N32 C44 O33 178.0(5) . . . . ? C43 N32 C44 N33 -1.6(7) . . . . ? O33 C44 N33 C40 -169.9(4) . . . . ? N32 C44 N33 C40 9.7(7) . . . . ? N31 C40 N33 C44 44.6(7) . . . . ? C41 C40 N33 C44 159.4(5) . . . . ? N32 C43 C45 C46 -63.5(6) . . . . ? C42 C43 C45 C46 173.6(5) . . . . ? C43 C45 C46 C47 127.6(6) . . . . ? C43 C45 C46 C51 -52.1(7) . . . . ? C51 C46 C47 C48 -1.6(8) . . . . ? C45 C46 C47 C48 178.8(5) . . . . ? C46 C47 C48 C49 0.7(9) . . . . ? C47 C48 C49 C50 0.2(10) . . . . ? C48 C49 C50 C51 -0.1(10) . . . . ? C49 C50 C51 C46 -0.9(10) . . . . ? C47 C46 C51 C50 1.7(9) . . . . ? C45 C46 C51 C50 -178.7(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O33 0.86 2.23 3.072(6) 164.7 1_565 N3 H3 O63 0.86 2.03 2.885(6) 171.9 . N62 H62 O3 0.86 2.28 3.128(6) 168.3 . N63 H63 O33 0.86 2.08 2.913(6) 162.4 . N32 H32 O63 0.86 2.3 3.134(6) 163.7 . N33 H33 O3 0.86 2.08 2.914(6) 163 1_545 O91 H91A O2 0.923(10) 2.223(5) 3.075(11) 153.2(6) 1_545 O91 H91B O1 1.087(9) 1.863(5) 2.936(11) 168.1(6) . # Attachment 'compound1asolvate.cif' # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-08-08 at 10:04:52 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.2 # Request file : \wingx\files\archive.dat # CIF files read : 85c dreduc struct # # CCDC ELECTRONIC DATA DEPOSITION FORM (CIF) # # This electronic data deposition form can be used: # # (a) WHEN SUBMITTING A PAPER TO A JOURNAL FOR PUBLICATION or # (b) WHEN SUBMITTING A PRIVATE COMMUNICATION TO THE CCDC # # A comprehensive archive of CIF resources is maintained by the IUCr # at its Chester office. This can be accessed # by anonymous ftp to ftp.iucr.org # or via the WWW at http://www.iucr.org/cif/home.html # If data items in this form are not available or not applicable # then ignore these items # A few items specific to CCDC input are indicated by _ccdc_ # # Submission and help information is provided at the end of this form #------------------------------------------------------------------------- data_85c _database_code_depnum_ccdc_archive 'CCDC 617812' _audit_creation_date 2006-08-08T10:04:52-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H15 N3 O2' _chemical_formula_sum 'C12 H15 N3 O2' _chemical_formula_weight 233.27 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M 'P 61' _symmetry_space_group_name_Hall 'P 61' _symmetry_Int_Tables_number 169 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' 'x-y, x, z+1/6' 'y, -x+y, z+5/6' _cell_length_a 15.3543(11) _cell_length_b 15.3543(11) _cell_length_c 9.7571(17) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 1992.1(4) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 18031 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 26.03 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.167 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.1176E-3 _diffrn_orient_matrix_ub_12 -0.650669E-1 _diffrn_orient_matrix_ub_13 0.9084E-3 _diffrn_orient_matrix_ub_21 0.740591E-1 _diffrn_orient_matrix_ub_22 0.370295E-1 _diffrn_orient_matrix_ub_23 -0.178136E-1 _diffrn_orient_matrix_ub_31 0.130705E-1 _diffrn_orient_matrix_ub_32 0.71214E-2 _diffrn_orient_matrix_ub_33 0.100925 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.063 _diffrn_reflns_av_unetI/netI 0.0275 _diffrn_reflns_number 18031 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 26.03 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_total 1373 _reflns_number_gt 1217 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1363P)^2^+0.8482P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 1373 _refine_ls_number_parameters 154 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0727 _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.1832 _refine_ls_wR_factor_gt 0.174 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.826 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.083 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.7682(3) 0.1802(3) 0.8443(4) 0.0209(9) Uani 1 1 d . . . H1A H 0.7769 0.1733 0.9414 0.025 Uiso 1 1 calc R . . H1B H 0.7197 0.1143 0.8094 0.025 Uiso 1 1 calc R . . N1 N 0.8639(3) 0.2146(3) 0.7749(4) 0.0219(8) Uani 1 1 d . . . C2 C 0.9553(4) 0.2470(4) 0.8552(6) 0.0357(13) Uani 1 1 d . . . H2A H 0.9388 0.2379 0.9509 0.054 Uiso 1 1 calc R . . H2B H 1.0017 0.3167 0.8373 0.054 Uiso 1 1 calc R . . H2C H 0.9856 0.2076 0.83 0.054 Uiso 1 1 calc R . . C3 C 0.8695(3) 0.2207(3) 0.6353(5) 0.0203(9) Uani 1 1 d . . . O1 O 0.9497(2) 0.2554(3) 0.5739(3) 0.0276(8) Uani 1 1 d . . . C4 C 0.7678(3) 0.1778(3) 0.5621(5) 0.0183(9) Uani 1 1 d . . . H4 H 0.7225 0.1099 0.597 0.022 Uiso 1 1 calc R . . C5 C 0.7813(3) 0.1718(3) 0.4083(4) 0.0201(9) Uani 1 1 d . . . H5A H 0.8117 0.239 0.37 0.024 Uiso 1 1 calc R . . H5B H 0.8274 0.1468 0.3931 0.024 Uiso 1 1 calc R . . C6 C 0.6836(3) 0.1044(3) 0.3325(4) 0.0182(9) Uani 1 1 d . . . C7 C 0.6508(3) 0.1418(3) 0.2273(5) 0.0206(9) Uani 1 1 d . . . H7 H 0.6874 0.2097 0.205 0.025 Uiso 1 1 calc R . . C8 C 0.5637(4) 0.0786(4) 0.1553(5) 0.0285(11) Uani 1 1 d . . . H8 H 0.5425 0.1047 0.0851 0.034 Uiso 1 1 calc R . . C9 C 0.5082(3) -0.0226(4) 0.1867(6) 0.0304(11) Uani 1 1 d . . . H9 H 0.4503 -0.0648 0.1374 0.037 Uiso 1 1 calc R . . C10 C 0.5399(4) -0.0605(3) 0.2928(6) 0.0285(11) Uani 1 1 d . . . H10 H 0.5024 -0.1283 0.3158 0.034 Uiso 1 1 calc R . . C11 C 0.6274(3) 0.0024(3) 0.3648(5) 0.0232(9) Uani 1 1 d . . . H11 H 0.6485 -0.0237 0.435 0.028 Uiso 1 1 calc R . . N2 N 0.7214(3) 0.2408(3) 0.5858(4) 0.0184(8) Uani 1 1 d . . . H2 H 0.704 0.2601 0.5133 0.022 Uiso 1 1 calc R . . C12 C 0.7029(3) 0.2722(3) 0.7060(4) 0.0158(8) Uani 1 1 d . . . O2 O 0.6631(2) 0.3273(2) 0.7056(4) 0.0199(6) Uani 1 1 d . . . N3 N 0.7285(3) 0.2483(3) 0.8260(4) 0.0199(8) Uani 1 1 d . . . H3 H 0.7207 0.2755 0.8986 0.024 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 C1 0.023(2) 0.023(2) 0.019(2) -0.0013(18) -0.0024(17) 0.0135(19) N1 0.0214(19) 0.0240(19) 0.0200(19) -0.0011(16) -0.0029(15) 0.0111(16) C2 0.025(2) 0.050(3) 0.027(3) -0.002(2) -0.009(2) 0.015(2) C3 0.016(2) 0.018(2) 0.024(2) -0.0016(18) -0.0020(17) 0.0068(17) O1 0.0190(16) 0.0330(17) 0.0267(19) -0.0057(14) -0.0018(13) 0.0100(14) C4 0.0162(19) 0.017(2) 0.021(2) -0.0036(17) -0.0001(16) 0.0086(17) C5 0.019(2) 0.019(2) 0.021(2) -0.0009(17) 0.0013(16) 0.0085(18) C6 0.0201(19) 0.0166(19) 0.019(2) -0.0038(16) -0.0010(16) 0.0097(17) C7 0.021(2) 0.0172(19) 0.024(2) -0.0019(17) -0.0021(18) 0.0102(17) C8 0.027(2) 0.033(3) 0.031(2) -0.001(2) -0.006(2) 0.018(2) C9 0.019(2) 0.029(2) 0.038(3) -0.006(2) -0.008(2) 0.0073(18) C10 0.024(2) 0.017(2) 0.036(3) 0.001(2) 0.001(2) 0.0036(18) C11 0.026(2) 0.021(2) 0.019(2) 0.0007(19) -0.0014(19) 0.0096(18) N2 0.0190(17) 0.0209(18) 0.0178(17) 0.0010(14) 0.0020(14) 0.0119(15) C12 0.0109(17) 0.0143(17) 0.019(2) -0.0008(17) 0.0000(16) 0.0037(15) O2 0.0225(15) 0.0219(15) 0.0176(14) -0.0021(13) -0.0011(12) 0.0128(13) N3 0.0266(19) 0.0217(18) 0.0146(18) -0.0004(14) 0.0020(14) 0.0145(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 N1 1.456(6) . ? C1 N3 1.462(6) . ? N1 C3 1.365(6) . ? N1 C2 1.460(6) . ? C3 O1 1.226(5) . ? C3 C4 1.535(6) . ? C4 N2 1.479(5) . ? C4 C5 1.524(6) . ? C5 C6 1.522(6) . ? C6 C7 1.389(6) . ? C6 C11 1.394(6) . ? C7 C8 1.387(7) . ? C8 C9 1.383(7) . ? C9 C10 1.390(7) . ? C10 C11 1.391(7) . ? N2 C12 1.352(5) . ? C12 O2 1.265(5) . ? C12 N3 1.344(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N3 113.0(3) . . ? C3 N1 C1 120.4(4) . . ? C3 N1 C2 119.7(4) . . ? C1 N1 C2 119.9(4) . . ? O1 C3 N1 122.2(4) . . ? O1 C3 C4 123.0(4) . . ? N1 C3 C4 114.8(4) . . ? N2 C4 C5 108.6(4) . . ? N2 C4 C3 111.4(3) . . ? C5 C4 C3 110.1(4) . . ? C6 C5 C4 113.7(4) . . ? C7 C6 C11 118.9(4) . . ? C7 C6 C5 121.1(4) . . ? C11 C6 C5 120.0(4) . . ? C8 C7 C6 120.5(4) . . ? C9 C8 C7 120.7(4) . . ? C8 C9 C10 119.2(4) . . ? C9 C10 C11 120.3(4) . . ? C10 C11 C6 120.4(4) . . ? C12 N2 C4 128.7(4) . . ? O2 C12 N3 119.3(4) . . ? O2 C12 N2 119.6(4) . . ? N3 C12 N2 121.1(3) . . ? C12 N3 C1 125.9(3) . . ?