# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full CrystEngComm #TrackingRef '- PANA-CEC-CIF.txt' _journal_coden_Cambridge 1350 _publ_contact_author_name 'Srinivasulu Aitipamula' _publ_contact_author_address ; Institute of Chemical and Engineering Sciences, A*STAR (Agency for Science, Technology and Research), 1, Pesek Road, Jurong Island, Singapore, 627833. ; _publ_contact_author_email 'srinivasulu aitipamula@ices.a-star.edu.sg' _publ_contact_author_phone '(65) 6796 3858' _publ_contact_author_fax '(65) 6316 6183' loop_ _publ_author_name _publ_author_address S.Aitipamula ; Institute of Chemical and Engineering Sciences, A*STAR (Agency for Science, Technology and Research), 1, Pesek Road, Jurong Island, Singapore, 627833. ; A.B.H.Wong ; Institute of Chemical and Engineering Sciences, A*STAR (Agency for Science, Technology and Research), 1, Pesek Road, Jurong Island, Singapore, 627833. ; P.S.Chow ; Institute of Chemical and Engineering Sciences, A*STAR (Agency for Science, Technology and Research), 1, Pesek Road, Jurong Island, Singapore, 627833. ; R.B.H.Tan ; Institute of Chemical and Engineering Sciences, A*STAR (Agency for Science, Technology and Research), 1, Pesek Road, Jurong Island, Singapore, 627833. Department of Chemical & Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, Singapore 117576. ; data_PANAF1 _database_code_depnum_ccdc_archive 'CCDC 885840' #TrackingRef '- PANA-CEC-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Form 1 of 1:1 nicotinamide and pimelic acid' ; _chemical_name_common "'Form 1 of 1:1 nicotinamide and pimelic acid'" _chemical_melting_point '383 K' _chemical_formula_moiety 'C7 H12 O4, C6 H6 N2 O' _chemical_formula_sum 'C13 H18 N2 O5' _chemical_formula_weight 282.29 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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4242(11) _cell_length_b 7.3161(15) _cell_length_c 17.917(4) _cell_angle_alpha 99.69(3) _cell_angle_beta 94.01(3) _cell_angle_gamma 103.93(3) _cell_volume 675.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2085 _cell_measurement_theta_min 2.3219 _cell_measurement_theta_max 31.0442 _exptl_crystal_description Plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9543 _exptl_absorpt_correction_T_max 0.9883 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9535 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3289 _reflns_number_gt 2972 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0895P)^2^+0.1493P] 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 3289 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1560 _refine_ls_wR_factor_gt 0.1504 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.144 _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 O5 O 0.1253(2) 0.74675(15) 0.15330(6) 0.0256(3) Uani 1 1 d . . . N1 N -0.1322(2) 0.79917(17) 0.75662(7) 0.0224(3) Uani 1 1 d . . . O4 O -0.27554(19) 0.56679(15) 0.12280(6) 0.0265(3) Uani 1 1 d . . . O2 O 0.7701(2) 0.81379(16) 0.56788(6) 0.0296(3) Uani 1 1 d . . . O3 O 0.4785(2) 0.71794(17) 0.64498(6) 0.0288(3) Uani 1 1 d . . . O1 O 0.1529(2) 0.82336(15) 1.01715(6) 0.0267(3) Uani 1 1 d . . . C1 C 0.0222(3) 0.81179(19) 0.88689(7) 0.0202(3) Uani 1 1 d . . . C8 C 0.3238(3) 0.6942(2) 0.51733(8) 0.0232(3) Uani 1 1 d . . . H8A H 0.1977 0.7649 0.5349 0.028 Uiso 1 1 calc R . . H8B H 0.2426 0.5557 0.5130 0.028 Uiso 1 1 calc R . . C11 C 0.1647(3) 0.7000(2) 0.30304(7) 0.0219(3) Uani 1 1 d . . . H11A H 0.2306 0.8389 0.3040 0.026 Uiso 1 1 calc R . . H11B H 0.2906 0.6338 0.2818 0.026 Uiso 1 1 calc R . . C12 C -0.0899(3) 0.6245(2) 0.25260(8) 0.0216(3) Uani 1 1 d . . . H12A H -0.1560 0.4871 0.2546 0.026 Uiso 1 1 calc R . . H12B H -0.2123 0.6927 0.2749 0.026 Uiso 1 1 calc R . . C6 C -0.0206(3) 0.7598(2) 0.96294(8) 0.0219(3) Uani 1 1 d . . . C13 C -0.0887(3) 0.64251(19) 0.17000(8) 0.0209(3) Uani 1 1 d . . . C9 C 0.3799(3) 0.7311(2) 0.43824(8) 0.0220(3) Uani 1 1 d . . . H9A H 0.4573 0.8695 0.4410 0.026 Uiso 1 1 calc R . . H9B H 0.5032 0.6595 0.4190 0.026 Uiso 1 1 calc R . . C7 C 0.5500(3) 0.74998(19) 0.57729(8) 0.0214(3) Uani 1 1 d . . . N2 N -0.2425(3) 0.6452(2) 0.97012(8) 0.0343(3) Uani 1 1 d . . . C2 C -0.1700(3) 0.75670(19) 0.82556(8) 0.0219(3) Uani 1 1 d . . . H2 H -0.3349 0.6860 0.8329 0.026 Uiso 1 1 calc R . . C10 C 0.1327(3) 0.6668(2) 0.38406(8) 0.0245(3) Uani 1 1 d . . . H10A H 0.0096 0.7363 0.4050 0.029 Uiso 1 1 calc R . . H10B H 0.0581 0.5282 0.3820 0.029 Uiso 1 1 calc R . . C3 C 0.1006(3) 0.8973(2) 0.74638(8) 0.0231(3) Uani 1 1 d . . . H3 H 0.1292 0.9251 0.6973 0.028 Uiso 1 1 calc R . . C4 C 0.3028(3) 0.9606(2) 0.80441(8) 0.0241(3) Uani 1 1 d . . . H4 H 0.4653 1.0318 0.7953 0.029 Uiso 1 1 calc R . . C5 C 0.2629(3) 0.9179(2) 0.87597(8) 0.0229(3) Uani 1 1 d . . . H5 H 0.3974 0.9602 0.9168 0.027 Uiso 1 1 calc R . . H1 H -0.256(4) 0.623(3) 1.0191(13) 0.043(6) Uiso 1 1 d . . . H13 H 0.122(4) 0.763(3) 0.1029(13) 0.040(5) Uiso 1 1 d . . . H7 H 0.625(5) 0.744(4) 0.6835(16) 0.065(8) Uiso 1 1 d . . . H6 H -0.379(5) 0.592(4) 0.9291(16) 0.060(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 O5 0.0210(5) 0.0337(6) 0.0182(5) 0.0073(4) 0.0004(4) -0.0011(4) N1 0.0219(6) 0.0261(6) 0.0184(5) 0.0037(4) 0.0010(4) 0.0054(5) O4 0.0220(5) 0.0323(6) 0.0201(5) 0.0060(4) -0.0027(4) -0.0017(4) O2 0.0213(5) 0.0412(6) 0.0244(5) 0.0084(4) 0.0012(4) 0.0036(4) O3 0.0233(5) 0.0438(6) 0.0175(5) 0.0079(4) 0.0005(4) 0.0042(4) O1 0.0232(5) 0.0337(6) 0.0194(5) 0.0069(4) -0.0010(4) -0.0001(4) C1 0.0219(7) 0.0216(6) 0.0170(6) 0.0042(5) 0.0018(5) 0.0049(5) C8 0.0195(6) 0.0313(7) 0.0174(6) 0.0044(5) 0.0001(5) 0.0042(5) C11 0.0211(7) 0.0252(6) 0.0183(6) 0.0057(5) 0.0003(5) 0.0032(5) C12 0.0208(6) 0.0250(6) 0.0182(6) 0.0058(5) 0.0021(5) 0.0031(5) C6 0.0212(7) 0.0247(6) 0.0182(6) 0.0038(5) -0.0005(5) 0.0037(5) C13 0.0211(6) 0.0215(6) 0.0193(6) 0.0040(5) 0.0007(5) 0.0041(5) C9 0.0221(7) 0.0255(7) 0.0175(6) 0.0052(5) 0.0009(5) 0.0042(5) C7 0.0227(7) 0.0225(6) 0.0194(6) 0.0038(5) 0.0022(5) 0.0069(5) N2 0.0266(7) 0.0462(8) 0.0220(6) 0.0123(6) -0.0023(5) -0.0087(6) C2 0.0206(7) 0.0236(6) 0.0208(6) 0.0046(5) 0.0018(5) 0.0040(5) C10 0.0222(7) 0.0306(7) 0.0191(6) 0.0065(5) 0.0006(5) 0.0033(5) C3 0.0254(7) 0.0237(6) 0.0208(6) 0.0059(5) 0.0044(5) 0.0059(5) C4 0.0203(7) 0.0259(7) 0.0252(7) 0.0065(5) 0.0035(5) 0.0031(5) C5 0.0210(7) 0.0244(6) 0.0218(6) 0.0048(5) 0.0008(5) 0.0035(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 O5 C13 1.3107(17) . ? O5 H13 0.93(2) . ? N1 C3 1.3357(19) . ? N1 C2 1.3410(17) . ? O4 C13 1.2250(18) . ? O2 C7 1.2075(18) . ? O3 C7 1.3394(17) . ? O3 H7 0.97(3) . ? O1 C6 1.2469(18) . ? C1 C5 1.3946(19) . ? C1 C2 1.395(2) . ? C1 C6 1.4938(18) . ? C8 C7 1.501(2) . ? C8 C9 1.5242(18) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C11 C12 1.523(2) . ? C11 C10 1.5264(18) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.5081(18) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C6 N2 1.3191(19) . ? C9 C10 1.524(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? N2 H1 0.92(2) . ? N2 H6 0.96(3) . ? C2 H2 0.9500 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C3 C4 1.390(2) . ? C3 H3 0.9500 . ? C4 C5 1.3891(19) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? 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 C13 O5 H13 114.5(13) . . ? C3 N1 C2 118.31(13) . . ? C7 O3 H7 111.9(16) . . ? C5 C1 C2 118.27(12) . . ? C5 C1 C6 119.33(13) . . ? C2 C1 C6 122.40(12) . . ? C7 C8 C9 115.95(12) . . ? C7 C8 H8A 108.3 . . ? C9 C8 H8A 108.3 . . ? C7 C8 H8B 108.3 . . ? C9 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? C12 C11 C10 110.51(11) . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C13 C12 C11 116.94(11) . . ? C13 C12 H12A 108.1 . . ? C11 C12 H12A 108.1 . . ? C13 C12 H12B 108.1 . . ? C11 C12 H12B 108.1 . . ? H12A C12 H12B 107.3 . . ? O1 C6 N2 122.03(13) . . ? O1 C6 C1 119.67(12) . . ? N2 C6 C1 118.30(13) . . ? O4 C13 O5 123.09(13) . . ? O4 C13 C12 122.08(12) . . ? O5 C13 C12 114.83(12) . . ? C10 C9 C8 109.66(11) . . ? C10 C9 H9A 109.7 . . ? C8 C9 H9A 109.7 . . ? C10 C9 H9B 109.7 . . ? C8 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? O2 C7 O3 122.70(13) . . ? O2 C7 C8 126.22(13) . . ? O3 C7 C8 111.08(12) . . ? C6 N2 H1 113.1(14) . . ? C6 N2 H6 123.9(15) . . ? H1 N2 H6 123(2) . . ? N1 C2 C1 122.90(13) . . ? N1 C2 H2 118.6 . . ? C1 C2 H2 118.6 . . ? C9 C10 C11 114.39(11) . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? N1 C3 C4 122.84(13) . . ? N1 C3 H3 118.6 . . ? C4 C3 H3 118.6 . . ? C5 C4 C3 118.81(13) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 C1 118.85(13) . . ? C4 C5 H5 120.6 . . ? C1 C5 H5 120.6 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.431 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.060 #====END data_PANAF2 _database_code_depnum_ccdc_archive 'CCDC 885841' #TrackingRef '- PANA-CEC-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Form 2 of 1:1 nicotinamide and pimelic acid' ; _chemical_name_common "'Form 2 of 1:1 nicotinamide and pimelic acid'" _chemical_melting_point '383 K' _chemical_formula_moiety 'C7 H12 O4, C6 H6 N2 O' _chemical_formula_sum 'C13 H18 N2 O5' _chemical_formula_weight 282.29 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' '-x, -y, z+1/2' _cell_length_a 9.290(7) _cell_length_b 31.04(2) _cell_length_c 4.981(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1436.3(18) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 3444 _cell_measurement_theta_min 2.2884 _cell_measurement_theta_max 31.0891 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9569 _exptl_absorpt_correction_T_max 0.9900 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6575 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 31.11 _reflns_number_total 3160 _reflns_number_gt 2609 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0975P)^2^+0.5896P] 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_number_reflns 3160 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0792 _refine_ls_wR_factor_ref 0.2164 _refine_ls_wR_factor_gt 0.2012 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.9605(3) 0.31040(8) 1.0330(6) 0.0431(6) Uani 1 1 d . . . O5 O 0.0750(3) 0.38143(8) 1.2108(6) 0.0467(7) Uani 1 1 d . . . O3 O 0.5651(3) 0.62177(8) 0.6409(7) 0.0454(7) Uani 1 1 d . . . C1 C 0.8430(4) 0.26128(12) 0.7394(8) 0.0366(7) Uani 1 1 d . . . O2 O 0.3665(3) 0.65884(8) 0.7410(6) 0.0486(7) Uani 1 1 d . . . N2 N 0.8684(4) 0.33758(9) 0.6506(8) 0.0444(8) Uani 1 1 d . . . H1 H 0.8987 0.3637 0.6889 0.053 Uiso 1 1 calc R . . H6 H 0.8210 0.3328 0.5005 0.053 Uiso 1 1 calc R . . C9 C 0.3221(5) 0.55840(11) 0.8737(9) 0.0449(9) Uani 1 1 d . . . H9A H 0.2301 0.5711 0.8119 0.054 Uiso 1 1 calc R . . H9B H 0.3705 0.5456 0.7157 0.054 Uiso 1 1 calc R . . C7 C 0.4472(4) 0.62833(11) 0.7791(8) 0.0395(8) Uani 1 1 d . . . N1 N 0.8626(3) 0.18542(9) 0.8236(7) 0.0386(7) Uani 1 1 d . . . C3 C 0.7664(4) 0.17840(11) 0.6261(8) 0.0394(8) Uani 1 1 d . . . H3 H 0.7388 0.1496 0.5868 0.047 Uiso 1 1 calc R . . C6 C 0.8941(4) 0.30550(11) 0.8182(8) 0.0359(7) Uani 1 1 d . . . O4 O 0.0147(4) 0.41666(9) 0.8381(7) 0.0598(9) Uani 1 1 d . . . C13 C 0.0774(4) 0.41542(11) 1.0500(9) 0.0395(8) Uani 1 1 d . . . C11 C 0.1984(5) 0.48693(12) 0.9613(9) 0.0496(10) Uani 1 1 d . . . H11A H 0.1062 0.4992 0.8974 0.060 Uiso 1 1 calc R . . H11B H 0.2485 0.4743 0.8046 0.060 Uiso 1 1 calc R . . C12 C 0.1673(4) 0.45160(11) 1.1630(9) 0.0398(8) Uani 1 1 d . . . H12A H 0.2596 0.4397 1.2285 0.048 Uiso 1 1 calc R . . H12B H 0.1164 0.4643 1.3188 0.048 Uiso 1 1 calc R . . C8 C 0.4174(4) 0.59439(11) 0.9880(8) 0.0416(8) Uani 1 1 d . . . H8A H 0.3688 0.6078 1.1440 0.050 Uiso 1 1 calc R . . H8B H 0.5096 0.5820 1.0509 0.050 Uiso 1 1 calc R . . C10 C 0.2901(5) 0.52283(11) 1.0765(8) 0.0424(8) Uani 1 1 d . . . H10A H 0.3821 0.5106 1.1410 0.051 Uiso 1 1 calc R . . H10B H 0.2398 0.5355 1.2328 0.051 Uiso 1 1 calc R . . C4 C 0.7061(5) 0.21156(12) 0.4783(9) 0.0436(9) Uani 1 1 d . . . H4 H 0.6382 0.2056 0.3405 0.052 Uiso 1 1 calc R . . C5 C 0.7463(4) 0.25357(12) 0.5344(9) 0.0428(8) Uani 1 1 d . . . H5 H 0.7078 0.2768 0.4332 0.051 Uiso 1 1 calc R . . C2 C 0.8994(4) 0.22637(11) 0.8778(8) 0.0403(8) Uani 1 1 d . . . H2 H 0.9671 0.2316 1.0170 0.048 Uiso 1 1 calc R . . H13 H 0.038(8) 0.361(2) 1.116(19) 0.12(3) Uiso 1 1 d . . . H7 H 0.579(8) 0.646(2) 0.551(17) 0.11(3) 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 O1 0.0529(14) 0.0394(12) 0.0369(15) 0.0027(11) -0.0120(14) -0.0038(11) O5 0.0650(17) 0.0373(12) 0.0378(16) 0.0077(11) -0.0110(15) -0.0087(12) O3 0.0462(14) 0.0378(12) 0.0522(18) 0.0059(12) 0.0117(14) 0.0056(10) C1 0.0369(15) 0.0424(15) 0.0305(17) 0.0010(14) -0.0046(16) -0.0010(13) O2 0.0555(15) 0.0442(13) 0.0461(18) 0.0034(12) 0.0124(15) 0.0097(12) N2 0.0566(19) 0.0381(13) 0.0383(17) 0.0045(14) -0.0133(17) -0.0080(13) C9 0.061(2) 0.0368(16) 0.037(2) 0.0003(15) -0.006(2) -0.0053(16) C7 0.0453(18) 0.0369(15) 0.036(2) -0.0016(14) 0.0024(16) -0.0042(13) N1 0.0428(15) 0.0392(14) 0.0338(17) 0.0002(12) -0.0055(14) -0.0030(12) C3 0.0442(18) 0.0403(16) 0.0338(19) 0.0008(14) -0.0010(17) -0.0028(14) C6 0.0397(16) 0.0390(15) 0.0289(17) 0.0007(14) -0.0044(15) 0.0012(13) O4 0.086(2) 0.0464(14) 0.0474(18) 0.0075(14) -0.0295(19) -0.0152(15) C13 0.0464(18) 0.0356(15) 0.036(2) 0.0027(14) -0.0027(18) 0.0018(14) C11 0.065(2) 0.0438(18) 0.040(2) 0.0060(17) -0.008(2) -0.0100(18) C12 0.0433(17) 0.0369(15) 0.039(2) 0.0008(15) -0.0071(18) -0.0003(13) C8 0.0454(18) 0.0434(17) 0.036(2) 0.0037(16) -0.0017(17) -0.0058(15) C10 0.0511(19) 0.0356(15) 0.041(2) 0.0012(15) -0.0045(18) -0.0026(14) C4 0.051(2) 0.0437(17) 0.036(2) -0.0009(16) -0.0091(18) -0.0027(16) C5 0.0470(19) 0.0413(17) 0.040(2) 0.0037(15) -0.0075(19) -0.0009(15) C2 0.0451(18) 0.0386(16) 0.037(2) 0.0010(15) -0.0034(17) -0.0012(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.244(5) . ? O5 C13 1.325(4) . ? O5 H13 0.86(8) . ? O3 C7 1.310(5) . ? O3 H7 0.87(7) . ? C1 C5 1.381(5) . ? C1 C2 1.387(5) . ? C1 C6 1.504(5) . ? O2 C7 1.222(4) . ? N2 C6 1.321(5) . ? N2 H1 0.8800 . ? N2 H6 0.8800 . ? C9 C10 1.525(5) . ? C9 C8 1.535(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C7 C8 1.506(5) . ? N1 C2 1.344(4) . ? N1 C3 1.347(5) . ? C3 C4 1.384(5) . ? C3 H3 0.9500 . ? O4 C13 1.206(5) . ? C13 C12 1.508(5) . ? C11 C12 1.515(5) . ? C11 C10 1.515(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C4 C5 1.385(5) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C2 H2 0.9500 . ? 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 C13 O5 H13 105(6) . . ? C7 O3 H7 105(5) . . ? C5 C1 C2 118.5(3) . . ? C5 C1 C6 123.8(3) . . ? C2 C1 C6 117.6(3) . . ? C6 N2 H1 120.0 . . ? C6 N2 H6 120.0 . . ? H1 N2 H6 120.0 . . ? C10 C9 C8 113.2(3) . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9B 108.9 . . ? C8 C9 H9B 108.9 . . ? H9A C9 H9B 107.8 . . ? O2 C7 O3 123.5(4) . . ? O2 C7 C8 122.5(4) . . ? O3 C7 C8 114.1(3) . . ? C2 N1 C3 117.9(3) . . ? N1 C3 C4 122.5(3) . . ? N1 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? O1 C6 N2 122.7(3) . . ? O1 C6 C1 119.5(3) . . ? N2 C6 C1 117.8(3) . . ? O4 C13 O5 123.1(3) . . ? O4 C13 C12 124.8(3) . . ? O5 C13 C12 112.1(3) . . ? C12 C11 C10 112.9(3) . . ? C12 C11 H11A 109.0 . . ? C10 C11 H11A 109.0 . . ? C12 C11 H11B 109.0 . . ? C10 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C11 113.4(3) . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C7 C8 C9 111.0(3) . . ? C7 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? C7 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C11 C10 C9 113.0(3) . . ? C11 C10 H10A 109.0 . . ? C9 C10 H10A 109.0 . . ? C11 C10 H10B 109.0 . . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C3 C4 C5 118.9(4) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C1 C5 C4 119.2(4) . . ? C1 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? N1 C2 C1 122.9(4) . . ? N1 C2 H2 118.6 . . ? C1 C2 H2 118.6 . . ? _diffrn_measured_fraction_theta_max 0.904 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.299 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.060 #====END