# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4h3nba_isonic _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Isonicotinamide 4-hydroxy-3-nitrobenzoic acid co-crystal' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 N O5, C6 H6 N2 O' _chemical_formula_sum 'C13 H11 N3 O6' _chemical_formula_weight 305.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.713(4) _cell_length_b 4.9822(2) _cell_length_c 25.526(4) _cell_angle_alpha 90.00 _cell_angle_beta 136.84(3) _cell_angle_gamma 90.00 _cell_volume 2584.9(15) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4046 _cell_measurement_theta_min 2.7932 _cell_measurement_theta_max 28.4990 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.48717 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcaliber' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3367 _diffrn_measurement_details ; 1 omega -56.00 35.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -21.2308 77.0000 300.0000 91 2 omega -15.00 106.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 22.6371 77.0000 150.0000 121 3 omega 0.00 45.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 22.6371 77.0000 240.0000 45 4 omega 82.00 121.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 22.6371 77.0000 240.0000 39 5 omega -2.00 121.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 22.6371 77.0000 30.0000 123 ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8582 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2635 _reflns_number_gt 1962 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2635 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0917 _refine_ls_wR_factor_gt 0.0882 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_restrained_S_all 0.942 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O10 O 0.01497(5) 0.4335(2) 0.62085(5) 0.0191(2) Uani 1 1 d . . . H10 H -0.0074 0.5618 0.6137 0.029 Uiso 1 1 calc R . . O13 O -0.23568(5) 1.4920(2) 0.46645(5) 0.0190(2) Uani 1 1 d . . . C25 C -0.14038(6) 1.2248(3) 0.55732(7) 0.0144(3) Uani 1 1 d . . . O22 O 0.06945(5) 0.48313(19) 0.74278(5) 0.0180(2) Uani 1 1 d . . . N32 N -0.05956(5) 0.8172(2) 0.58937(6) 0.0168(3) Uani 1 1 d . . . N19 N -0.17333(6) 1.5765(3) 0.59028(7) 0.0168(3) Uani 1 1 d . . . O8 O 0.23145(5) -0.4519(2) 0.77004(6) 0.0225(3) Uani 1 1 d . . . C11 C 0.10493(6) 0.1518(3) 0.71166(7) 0.0151(3) Uani 1 1 d . . . C5 C 0.13157(7) -0.1902(3) 0.67201(7) 0.0173(3) Uani 1 1 d . . . C9 C 0.18853(6) -0.2598(3) 0.74829(8) 0.0167(3) Uani 1 1 d . . . C14 C 0.06128(6) 0.3730(3) 0.69334(7) 0.0148(3) Uani 1 1 d . . . C31 C -0.04626(7) 0.9430(3) 0.64555(8) 0.0180(3) Uani 1 1 d . . . C28 C -0.11260(7) 0.8930(3) 0.51709(8) 0.0196(3) Uani 1 1 d . . . H28 H -0.1221 0.8052 0.4769 0.023 Uiso 1 1 calc R . . C27 C -0.08501(7) 1.1479(3) 0.63234(8) 0.0172(3) Uani 1 1 d . . . C26 C -0.15399(7) 1.0947(3) 0.49900(7) 0.0184(3) Uani 1 1 d . . . C17 C 0.16145(7) 0.0823(3) 0.78808(8) 0.0163(3) Uani 1 1 d . . . O2 O 0.14949(6) -0.5207(2) 0.62483(6) 0.0300(3) Uani 1 1 d . . . C18 C -0.18686(6) 1.4432(3) 0.53501(7) 0.0142(3) Uani 1 1 d . . . C15 C 0.20259(7) -0.1184(3) 0.80594(8) 0.0172(3) Uani 1 1 d . . . C7 C 0.09029(7) 0.0145(3) 0.65394(8) 0.0164(3) Uani 1 1 d . . . O1 O 0.06544(6) -0.2606(2) 0.54364(6) 0.0362(3) Uani 1 1 d . . . N3 N 0.11363(6) -0.3294(3) 0.60891(6) 0.0227(3) Uani 1 1 d . . . H15 H 0.2421(7) -0.169(3) 0.8592(8) 0.018(4) Uiso 1 1 d . . . H7 H 0.0529(8) 0.051(3) 0.6025(10) 0.021(4) Uiso 1 1 d . . . H31 H -0.0055(7) 0.879(3) 0.6986(8) 0.018(4) Uiso 1 1 d . . . H19B H -0.2017(8) 1.715(4) 0.5743(9) 0.031(5) Uiso 1 1 d . . . H17 H 0.1725(8) 0.184(3) 0.8292(9) 0.026(4) Uiso 1 1 d . . . H19A H -0.1403(8) 1.544(3) 0.6369(10) 0.019(4) Uiso 1 1 d . . . H26 H -0.1916(9) 1.149(4) 0.4460(10) 0.034(4) Uiso 1 1 d . . . H27 H -0.0716(8) 1.232(3) 0.6775(9) 0.030(4) Uiso 1 1 d . . . H8 H 0.2139(11) -0.522(5) 0.7283(13) 0.061(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O10 0.0161(5) 0.0211(6) 0.0145(5) 0.0023(4) 0.0094(4) 0.0066(4) O13 0.0162(5) 0.0201(5) 0.0139(5) 0.0011(4) 0.0088(4) 0.0033(4) C25 0.0127(6) 0.0138(7) 0.0164(6) 0.0002(5) 0.0105(6) -0.0021(5) O22 0.0167(5) 0.0201(5) 0.0156(5) -0.0009(4) 0.0112(4) 0.0011(4) N32 0.0147(6) 0.0166(6) 0.0178(6) -0.0003(5) 0.0114(5) -0.0003(5) N19 0.0146(6) 0.0174(6) 0.0133(6) 0.0007(5) 0.0085(5) 0.0027(5) O8 0.0198(5) 0.0238(6) 0.0231(5) 0.0002(5) 0.0154(5) 0.0058(4) C11 0.0124(7) 0.0159(7) 0.0163(6) 0.0007(6) 0.0102(6) -0.0002(5) C5 0.0186(7) 0.0188(7) 0.0178(7) -0.0031(6) 0.0143(6) -0.0031(6) C9 0.0144(7) 0.0166(7) 0.0215(7) 0.0009(6) 0.0139(6) 0.0001(5) C14 0.0113(6) 0.0157(7) 0.0146(6) 0.0001(6) 0.0085(5) -0.0020(5) C31 0.0143(7) 0.0201(7) 0.0158(6) 0.0009(6) 0.0097(6) 0.0007(6) C28 0.0194(7) 0.0201(8) 0.0165(6) -0.0017(6) 0.0123(6) 0.0006(6) C27 0.0153(7) 0.0184(7) 0.0158(6) -0.0007(6) 0.0108(6) 0.0003(6) C26 0.0157(7) 0.0200(8) 0.0134(6) 0.0003(6) 0.0087(6) 0.0008(6) C17 0.0144(7) 0.0190(7) 0.0152(6) -0.0013(6) 0.0107(6) -0.0015(6) O2 0.0320(6) 0.0302(6) 0.0305(6) -0.0034(5) 0.0236(5) 0.0069(5) C18 0.0126(6) 0.0141(7) 0.0153(6) 0.0007(5) 0.0100(6) -0.0017(5) C15 0.0128(7) 0.0202(8) 0.0149(6) 0.0016(6) 0.0089(6) 0.0001(6) C7 0.0134(7) 0.0193(8) 0.0150(6) 0.0004(6) 0.0099(6) -0.0012(5) O1 0.0352(7) 0.0454(8) 0.0163(5) -0.0011(5) 0.0151(5) 0.0100(6) N3 0.0245(7) 0.0248(7) 0.0221(6) -0.0031(5) 0.0180(6) 0.0000(5) _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 O10 C14 1.3014(17) . ? O10 H10 0.8400 . ? O13 C18 1.2340(17) . ? C25 C26 1.3862(19) . ? C25 C27 1.387(2) . ? C25 C18 1.5060(19) . ? O22 C14 1.2270(16) . ? N32 C31 1.3337(18) . ? N32 C28 1.3373(18) . ? N19 C18 1.3288(18) . ? N19 H19B 0.923(18) . ? N19 H19A 0.837(17) . ? O8 C9 1.3480(16) . ? O8 H8 0.85(2) . ? C11 C7 1.3757(19) . ? C11 C17 1.402(2) . ? C11 C14 1.4936(19) . ? C5 C7 1.390(2) . ? C5 C9 1.403(2) . ? C5 N3 1.4514(18) . ? C9 C15 1.3928(19) . ? C31 C27 1.384(2) . ? C31 H31 1.004(15) . ? C28 C26 1.381(2) . ? C28 H28 0.9500 . ? C27 H27 0.997(16) . ? C26 H26 0.973(17) . ? C17 C15 1.374(2) . ? C17 H17 0.981(16) . ? O2 N3 1.2557(16) . ? C15 H15 0.980(14) . ? C7 H7 0.929(17) . ? O1 N3 1.2097(16) . ? 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 C14 O10 H10 109.5 . . ? C26 C25 C27 118.46(13) . . ? C26 C25 C18 117.58(12) . . ? C27 C25 C18 123.96(12) . . ? C31 N32 C28 118.52(12) . . ? C18 N19 H19B 115.7(10) . . ? C18 N19 H19A 123.1(11) . . ? H19B N19 H19A 121.1(15) . . ? C9 O8 H8 104.2(15) . . ? C7 C11 C17 119.31(13) . . ? C7 C11 C14 120.50(12) . . ? C17 C11 C14 120.19(12) . . ? C7 C5 C9 121.40(12) . . ? C7 C5 N3 117.48(12) . . ? C9 C5 N3 121.12(13) . . ? O8 C9 C15 117.35(12) . . ? O8 C9 C5 124.62(12) . . ? C15 C9 C5 118.02(13) . . ? O22 C14 O10 124.72(12) . . ? O22 C14 C11 122.20(12) . . ? O10 C14 C11 113.08(12) . . ? N32 C31 C27 122.90(13) . . ? N32 C31 H31 114.9(8) . . ? C27 C31 H31 122.1(8) . . ? N32 C28 C26 122.19(13) . . ? N32 C28 H28 118.9 . . ? C26 C28 H28 118.9 . . ? C31 C27 C25 118.58(13) . . ? C31 C27 H27 117.9(9) . . ? C25 C27 H27 123.5(9) . . ? C28 C26 C25 119.34(13) . . ? C28 C26 H26 120.3(10) . . ? C25 C26 H26 120.3(10) . . ? C15 C17 C11 120.92(13) . . ? C15 C17 H17 119.9(9) . . ? C11 C17 H17 119.1(9) . . ? O13 C18 N19 122.67(13) . . ? O13 C18 C25 118.92(12) . . ? N19 C18 C25 118.41(12) . . ? C17 C15 C9 120.59(13) . . ? C17 C15 H15 121.5(9) . . ? C9 C15 H15 117.9(9) . . ? C11 C7 C5 119.75(13) . . ? C11 C7 H7 122.5(10) . . ? C5 C7 H7 117.8(10) . . ? O1 N3 O2 122.21(12) . . ? O1 N3 C5 120.06(13) . . ? O2 N3 C5 117.73(12) . . ? 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 O10 H10 N32 0.84 1.73 2.5710(15) 174.2 . N19 H19B O13 0.923(18) 1.963(19) 2.8841(17) 176.1(14) 7_486 N19 H19A O22 0.837(17) 2.127(17) 2.952(2) 168.3(15) 2_566 O8 H8 O2 0.85(2) 1.81(2) 2.5726(19) 149(2) . O8 H8 N3 0.85(2) 2.42(2) 2.922(2) 118.9(18) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.257 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.060 #END _database_code_depnum_ccdc_archive 'CCDC 960081' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_246_thba_isonic _audit_creation_method SHELXL-97 _chemical_name_systematic ; pyridinium-4-carboxamide 2,4,6-trihydroxybenzoate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 O5, C6 H7 N2 O' _chemical_formula_sum 'C13 H12 N2 O6' _chemical_formula_weight 292.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n a 21 ' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 12.8093(14) _cell_length_b 13.1563(12) _cell_length_c 7.4708(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1259.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Brown _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcaliber' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3367 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3392 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_sigmaI/netI 0.0816 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 3 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 28.42 _reflns_number_total 1817 _reflns_number_gt 1244 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0725P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(2) _refine_ls_number_reflns 1817 _refine_ls_number_parameters 204 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1321 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O16 O -0.5731(2) -0.6890(2) -0.2853(4) 0.0214(8) Uani 1 1 d . . . N4 N -0.9204(3) -0.7004(2) -0.5743(5) 0.0141(8) Uani 1 1 d . . . H4 H -0.9793 -0.7178 -0.6264 0.017 Uiso 1 1 calc R . . O31 O -0.4048(2) -0.2291(2) -0.2514(5) 0.0183(8) Uani 1 1 d . . . C9 C -0.7368(4) -0.6460(3) -0.4134(6) 0.0120(10) Uani 1 1 d . . . C26 C -0.2767(4) -0.3326(3) -0.3882(6) 0.0139(10) Uani 1 1 d . . . C20 C -0.1452(4) -0.4425(3) -0.5198(6) 0.0172(10) Uani 1 1 d . . . H20 H -0.1211 -0.5087 -0.5495 0.021 Uiso 1 1 calc R . . O25 O -0.2922(3) -0.5141(2) -0.3816(5) 0.0220(8) Uani 1 1 d . . . C5 C -0.8021(4) -0.5735(3) -0.4890(6) 0.0148(10) Uani 1 1 d . . . H5 H -0.7833 -0.5037 -0.4852 0.018 Uiso 1 1 calc R . . O17 O 0.0047(3) -0.3737(2) -0.6552(5) 0.0211(8) Uani 1 1 d . . . H17 H 0.0221 -0.3203 -0.7090 0.032 Uiso 1 1 calc R . . C18 C -0.0865(4) -0.3579(3) -0.5663(6) 0.0158(10) Uani 1 1 d . . . N14 N -0.6123(4) -0.5232(3) -0.3060(6) 0.0195(10) Uani 1 1 d . . . C24 C -0.2145(3) -0.2495(3) -0.4348(6) 0.0148(10) Uani 1 1 d . . . C22 C -0.2380(4) -0.4305(3) -0.4310(7) 0.0161(10) Uani 1 1 d . . . C21 C -0.1199(4) -0.2602(3) -0.5239(6) 0.0139(10) Uani 1 1 d . . . H21 H -0.0792 -0.2024 -0.5549 0.017 Uiso 1 1 calc R . . C3 C -0.8931(4) -0.6024(3) -0.5688(6) 0.0159(10) Uani 1 1 d . . . H3 H -0.9374 -0.5526 -0.6208 0.019 Uiso 1 1 calc R . . C6 C -0.8598(4) -0.7728(3) -0.5022(6) 0.0159(10) Uani 1 1 d . . . H6 H -0.8809 -0.8420 -0.5077 0.019 Uiso 1 1 calc R . . C13 C -0.6336(4) -0.6208(4) -0.3283(6) 0.0154(10) Uani 1 1 d . . . C29 C -0.3757(4) -0.3205(3) -0.2893(6) 0.0164(10) Uani 1 1 d . . . C10 C -0.7674(4) -0.7474(3) -0.4205(6) 0.0166(10) Uani 1 1 d . . . H10 H -0.7247 -0.7987 -0.3691 0.020 Uiso 1 1 calc R . . H14B H -0.653(4) -0.487(4) -0.336(8) 0.030(19) Uiso 1 1 d . . . H14A H -0.553(4) -0.506(4) -0.271(7) 0.022(15) Uiso 1 1 d . . . O0AA O -0.4277(2) -0.3974(2) -0.2422(5) 0.0194(8) Uani 1 1 d . . . O28 O -0.2465(3) -0.1533(2) -0.3925(5) 0.0182(8) Uani 1 1 d . . . H28 H -0.3099 -0.1543 -0.3640 0.027 Uiso 1 1 calc R . . H25 H -0.347(4) -0.496(5) -0.337(9) 0.05(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O16 0.0177(18) 0.0217(18) 0.0249(19) 0.0004(15) -0.0059(17) 0.0030(16) N4 0.0081(19) 0.0171(19) 0.0171(19) -0.0023(17) -0.0017(18) -0.0021(17) O31 0.0127(18) 0.0192(16) 0.0232(18) 0.0011(14) 0.0029(16) 0.0031(14) C9 0.010(2) 0.014(2) 0.012(2) -0.0045(18) 0.002(2) -0.0011(19) C26 0.014(2) 0.016(2) 0.012(2) 0.0027(18) -0.004(2) -0.0006(19) C20 0.020(3) 0.012(2) 0.020(2) -0.0022(19) 0.003(2) 0.000(2) O25 0.0226(19) 0.0126(17) 0.031(2) -0.0015(15) 0.0069(19) -0.0055(15) C5 0.017(2) 0.012(2) 0.015(2) -0.0023(18) -0.002(2) 0.000(2) O17 0.0192(18) 0.0205(15) 0.0236(17) 0.0013(15) 0.0100(16) 0.0014(16) C18 0.014(2) 0.021(2) 0.012(2) -0.0009(19) -0.001(2) 0.002(2) N14 0.012(2) 0.021(2) 0.025(2) -0.0037(19) -0.004(2) -0.001(2) C24 0.014(2) 0.016(2) 0.015(2) 0.000(2) -0.001(2) 0.004(2) C22 0.017(2) 0.015(2) 0.017(2) -0.0012(18) -0.002(2) 0.000(2) C21 0.014(2) 0.015(2) 0.013(2) 0.0005(18) -0.001(2) -0.001(2) C3 0.015(3) 0.015(2) 0.018(2) 0.0012(19) 0.003(2) 0.005(2) C6 0.016(2) 0.016(2) 0.016(2) 0.0011(18) 0.003(2) -0.001(2) C13 0.013(2) 0.019(2) 0.014(2) -0.0001(18) 0.000(2) -0.002(2) C29 0.011(2) 0.022(2) 0.017(2) 0.0020(19) -0.002(2) 0.002(2) C10 0.016(2) 0.018(2) 0.016(2) 0.002(2) 0.000(2) 0.003(2) O0AA 0.0144(17) 0.0208(17) 0.0231(18) 0.0027(14) 0.0005(17) -0.0060(14) O28 0.0155(17) 0.0108(14) 0.028(2) 0.0012(13) 0.0085(18) 0.0039(13) _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 O16 C13 1.229(5) . ? N4 C3 1.336(5) . ? N4 C6 1.342(6) . ? N4 H4 0.8800 . ? O31 C29 1.290(5) . ? C9 C5 1.388(6) . ? C9 C10 1.392(6) . ? C9 C13 1.504(6) . ? C26 C24 1.397(6) . ? C26 C22 1.416(6) . ? C26 C29 1.476(6) . ? C20 C22 1.371(7) . ? C20 C18 1.388(6) . ? C20 H20 0.9500 . ? O25 C22 1.352(5) . ? O25 H25 0.82(5) . ? C5 C3 1.364(6) . ? C5 H5 0.9500 . ? O17 C18 1.360(6) . ? O17 H17 0.8400 . ? C18 C21 1.392(6) . ? N14 C13 1.323(6) . ? N14 H14B 0.75(5) . ? N14 H14A 0.84(5) . ? C24 O28 1.368(5) . ? C24 C21 1.389(6) . ? C21 H21 0.9500 . ? C3 H3 0.9500 . ? C6 C10 1.373(6) . ? C6 H6 0.9500 . ? C29 O0AA 1.263(5) . ? C10 H10 0.9500 . ? O28 H28 0.8400 . ? 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 C3 N4 C6 121.4(4) . . ? C3 N4 H4 119.3 . . ? C6 N4 H4 119.3 . . ? C5 C9 C10 118.2(4) . . ? C5 C9 C13 123.3(4) . . ? C10 C9 C13 118.4(4) . . ? C24 C26 C22 117.1(4) . . ? C24 C26 C29 122.0(4) . . ? C22 C26 C29 120.8(4) . . ? C22 C20 C18 119.9(4) . . ? C22 C20 H20 120.0 . . ? C18 C20 H20 120.0 . . ? C22 O25 H25 109(4) . . ? C3 C5 C9 120.1(4) . . ? C3 C5 H5 120.0 . . ? C9 C5 H5 120.0 . . ? C18 O17 H17 109.5 . . ? O17 C18 C20 117.7(4) . . ? O17 C18 C21 121.1(4) . . ? C20 C18 C21 121.2(4) . . ? C13 N14 H14B 116(4) . . ? C13 N14 H14A 120(3) . . ? H14B N14 H14A 124(5) . . ? O28 C24 C21 117.7(4) . . ? O28 C24 C26 119.7(4) . . ? C21 C24 C26 122.5(4) . . ? O25 C22 C20 118.9(4) . . ? O25 C22 C26 119.9(4) . . ? C20 C22 C26 121.2(4) . . ? C24 C21 C18 118.1(4) . . ? C24 C21 H21 121.0 . . ? C18 C21 H21 121.0 . . ? N4 C3 C5 120.4(4) . . ? N4 C3 H3 119.8 . . ? C5 C3 H3 119.8 . . ? N4 C6 C10 120.2(4) . . ? N4 C6 H6 119.9 . . ? C10 C6 H6 119.9 . . ? O16 C13 N14 123.1(5) . . ? O16 C13 C9 120.2(4) . . ? N14 C13 C9 116.7(4) . . ? O0AA C29 O31 122.2(4) . . ? O0AA C29 C26 120.4(4) . . ? O31 C29 C26 117.4(4) . . ? C6 C10 C9 119.6(4) . . ? C6 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C24 O28 H28 109.5 . . ? 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 N4 H4 O31 0.88 1.76 2.628(5) 168.7 3_344 O17 H17 O16 0.84 1.93 2.760(4) 168.3 3_454 N14 H14B O28 0.75(5) 2.23(5) 2.960(6) 164(5) 4_445 N14 H14A O0AA 0.84(5) 2.15(5) 2.924(5) 153(5) . O28 H28 O31 0.84 1.78 2.494(5) 142.3 . O25 H25 O0AA 0.82(5) 1.80(6) 2.541(5) 150(6) . _diffrn_measured_fraction_theta_max 0.896 _diffrn_reflns_theta_full 27.35 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.426 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.200 #END _database_code_depnum_ccdc_archive 'CCDC 960082'