# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Samantha Callear' _publ_contact_author_email SAM.CALLEAR@STFC.AC.UK _publ_section_title ; A systematic study of the crystallisation products of a series of dicarboxylic acids with imidazole derivatives. ; loop_ _publ_author_name 'Samantha Callear' 'Mike Hursthouse' 'T Threlfall' # Attachment '1-9_rev.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 745369' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Suberic acid & imidazole ; _chemical_name_common 'Suberic acid & imidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H50 N4 O12' _chemical_formula_weight 658.74 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 8.7148(3) _cell_length_b 11.4826(3) _cell_length_c 16.9691(5) _cell_angle_alpha 81.721(2) _cell_angle_beta 81.814(2) _cell_angle_gamma 77.987(2) _cell_volume 1632.45(9) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7364 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9897 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34067 _diffrn_reflns_av_R_equivalents 0.0664 _diffrn_reflns_av_sigmaI/netI 0.0619 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7472 _reflns_number_gt 4927 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^)+(0.0592P)^2^+0.5404P] 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_extinction_coef ? _refine_ls_number_reflns 7472 _refine_ls_number_parameters 426 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0908 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1232 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 C1 C 0.0222(2) -0.08232(15) 0.42213(10) 0.0173(4) Uani 1 1 d . . . C2 C 0.1073(2) 0.00059(15) 0.36287(11) 0.0189(4) Uani 1 1 d . . . H2A H 0.1594 -0.0432 0.3170 0.023 Uiso 1 1 calc R . . H2B H 0.1914 0.0210 0.3889 0.023 Uiso 1 1 calc R . . C3 C 0.0045(2) 0.11631(15) 0.33064(11) 0.0198(4) Uani 1 1 d . . . H3A H -0.0406 0.1646 0.3752 0.024 Uiso 1 1 calc R . . H3B H -0.0840 0.0974 0.3074 0.024 Uiso 1 1 calc R . . C4 C 0.0996(2) 0.18935(16) 0.26645(11) 0.0208(4) Uani 1 1 d . . . H4A H 0.1822 0.2139 0.2913 0.025 Uiso 1 1 calc R . . H4B H 0.1531 0.1378 0.2247 0.025 Uiso 1 1 calc R . . C5 C -0.0018(2) 0.30088(15) 0.22685(11) 0.0192(4) Uani 1 1 d . . . H5A H -0.0593 0.3504 0.2689 0.023 Uiso 1 1 calc R . . H5B H -0.0813 0.2760 0.1999 0.023 Uiso 1 1 calc R . . C6 C 0.0930(2) 0.37729(15) 0.16545(11) 0.0195(4) Uani 1 1 d . . . H6A H 0.1711 0.4040 0.1923 0.023 Uiso 1 1 calc R . . H6B H 0.1516 0.3280 0.1235 0.023 Uiso 1 1 calc R . . C7 C -0.0127(2) 0.48660(15) 0.12636(10) 0.0173(4) Uani 1 1 d . . . H7A H -0.0838 0.4583 0.0959 0.021 Uiso 1 1 calc R . . H7B H -0.0797 0.5296 0.1694 0.021 Uiso 1 1 calc R . . C8 C 0.0706(2) 0.57558(15) 0.07016(10) 0.0160(4) Uani 1 1 d . . . O1A O -0.11571(15) -0.05885(11) 0.44900(8) 0.0238(3) Uani 1 1 d . . . O1B O 0.11728(14) -0.18611(11) 0.44107(8) 0.0222(3) Uani 1 1 d . . . H1 H 0.0655 -0.2324 0.4713 0.047(7) Uiso 1 1 calc R . . O8A O -0.01886(14) 0.66707(11) 0.03765(8) 0.0224(3) Uani 1 1 d . . . O8B O 0.21794(14) 0.55853(11) 0.05840(8) 0.0217(3) Uani 1 1 d . . . C22 C 0.5747(2) 0.65950(17) 0.03200(11) 0.0210(4) Uani 1 1 d . . . H22 H 0.6130 0.5777 0.0245 0.025 Uiso 1 1 calc R . . C24 C 0.4153(2) 0.83160(16) 0.04964(11) 0.0218(4) Uani 1 1 d . . . H24 H 0.3218 0.8906 0.0567 0.026 Uiso 1 1 calc R . . C25 C 0.5658(2) 0.84760(17) 0.04650(11) 0.0231(4) Uani 1 1 d . . . H25 H 0.5980 0.9203 0.0510 0.028 Uiso 1 1 calc R . . N21 N 0.66296(18) 0.73934(13) 0.03561(9) 0.0216(3) Uani 1 1 d . . . H21 H 0.7668 0.7252 0.0317 0.031(6) Uiso 1 1 calc R . . N23 N 0.42430(17) 0.71286(13) 0.04057(9) 0.0199(3) Uani 1 1 d . . . H23 H 0.3433 0.6782 0.0405 0.049(7) Uiso 1 1 calc R . . C31 C 0.9414(2) -0.57452(15) 0.42949(10) 0.0163(4) Uani 1 1 d . . . C32 C 1.0286(2) -0.48851(15) 0.37277(10) 0.0174(4) Uani 1 1 d . . . H32A H 1.1016 -0.4616 0.4028 0.021 Uiso 1 1 calc R . . H32B H 1.0935 -0.5328 0.3298 0.021 Uiso 1 1 calc R . . C33 C 0.9242(2) -0.37843(15) 0.33406(11) 0.0193(4) Uani 1 1 d . . . H33A H 0.8668 -0.3292 0.3763 0.023 Uiso 1 1 calc R . . H33B H 0.8450 -0.4043 0.3076 0.023 Uiso 1 1 calc R . . C34 C 1.0178(2) -0.30147(15) 0.27222(11) 0.0188(4) Uani 1 1 d . . . H34A H 1.0994 -0.2778 0.2983 0.023 Uiso 1 1 calc R . . H34B H 1.0724 -0.3499 0.2291 0.023 Uiso 1 1 calc R . . C35 C 0.9140(2) -0.18890(16) 0.23531(11) 0.0207(4) Uani 1 1 d . . . H35A H 0.8629 -0.1391 0.2784 0.025 Uiso 1 1 calc R . . H35B H 0.8293 -0.2127 0.2116 0.025 Uiso 1 1 calc R . . C36 C 1.0036(2) -0.11318(15) 0.17064(11) 0.0193(4) Uani 1 1 d . . . H36A H 1.0914 -0.0918 0.1932 0.023 Uiso 1 1 calc R . . H36B H 1.0497 -0.1607 0.1258 0.023 Uiso 1 1 calc R . . C37 C 0.8958(2) 0.00073(16) 0.13912(11) 0.0207(4) Uani 1 1 d . . . H37A H 0.8114 -0.0219 0.1146 0.025 Uiso 1 1 calc R . . H37B H 0.8446 0.0445 0.1851 0.025 Uiso 1 1 calc R . . C38 C 0.9760(2) 0.08434(15) 0.07844(10) 0.0170(4) Uani 1 1 d . . . O31A O 0.79437(14) -0.55643(11) 0.43787(8) 0.0220(3) Uani 1 1 d . . . O31B O 1.02722(14) -0.66445(11) 0.46585(7) 0.0217(3) Uani 1 1 d . . . O38A O 1.11423(15) 0.06309(11) 0.05101(8) 0.0239(3) Uani 1 1 d . . . O38B O 0.87816(14) 0.18596(11) 0.05842(8) 0.0225(3) Uani 1 1 d . . . H38 H 0.9271 0.2311 0.0254 0.058(8) Uiso 1 1 calc R . . C42 C 0.4339(2) -0.64631(16) 0.46753(11) 0.0209(4) Uani 1 1 d . . . H42 H 0.3999 -0.5626 0.4699 0.025 Uiso 1 1 calc R . . C44 C 0.5854(2) -0.82371(16) 0.45887(11) 0.0205(4) Uani 1 1 d . . . H44 H 0.6762 -0.8856 0.4542 0.025 Uiso 1 1 calc R . . C45 C 0.4328(2) -0.83596(16) 0.46488(11) 0.0218(4) Uani 1 1 d . . . H45 H 0.3964 -0.9085 0.4652 0.026 Uiso 1 1 calc R . . N41 N 0.34065(18) -0.72435(13) 0.47040(9) 0.0201(3) Uani 1 1 d . . . H41 H 0.2368 -0.7075 0.4751 0.039(7) Uiso 1 1 calc R . . N43 N 0.58284(17) -0.70411(13) 0.46082(9) 0.0197(3) Uani 1 1 d . . . H43 H 0.6664 -0.6712 0.4581 0.036(6) Uiso 1 1 calc R . . C51 C 0.5090(2) -0.07141(16) 0.28570(11) 0.0204(4) Uani 1 1 d . . . C52 C 0.4971(2) -0.19519(15) 0.32581(11) 0.0201(4) Uani 1 1 d . . . H52A H 0.4070 -0.1888 0.3687 0.024 Uiso 1 1 calc R . . H52B H 0.5942 -0.2294 0.3516 0.024 Uiso 1 1 calc R . . C53 C 0.4750(2) -0.28142(16) 0.27011(11) 0.0216(4) Uani 1 1 d . . . H53A H 0.5685 -0.2938 0.2295 0.026 Uiso 1 1 calc R . . H53B H 0.3814 -0.2461 0.2417 0.026 Uiso 1 1 calc R . . C54 C 0.4528(2) -0.40198(16) 0.31652(11) 0.0207(4) Uani 1 1 d . . . H54A H 0.3593 -0.3887 0.3571 0.025 Uiso 1 1 calc R . . H54B H 0.5461 -0.4360 0.3454 0.025 Uiso 1 1 calc R . . C55 C 0.4309(2) -0.49294(16) 0.26372(11) 0.0204(4) Uani 1 1 d . . . H55A H 0.3922 -0.5604 0.2983 0.024 Uiso 1 1 calc R . . H55B H 0.3494 -0.4544 0.2281 0.024 Uiso 1 1 calc R . . C56 C 0.5821(2) -0.54191(16) 0.21263(11) 0.0218(4) Uani 1 1 d . . . H56B H 0.6608 -0.5862 0.2483 0.026 Uiso 1 1 calc R . . H56A H 0.6255 -0.4739 0.1814 0.026 Uiso 1 1 calc R . . C57 C 0.5583(2) -0.62524(16) 0.15484(11) 0.0219(4) Uani 1 1 d . . . H57A H 0.4640 -0.5874 0.1276 0.026 Uiso 1 1 calc R . . H57B H 0.6507 -0.6339 0.1133 0.026 Uiso 1 1 calc R . . C58 C 0.5377(2) -0.74801(16) 0.19391(11) 0.0213(4) Uani 1 1 d . . . O51A O 0.55209(17) -0.00571(12) 0.33324(8) 0.0290(3) Uani 1 1 d . . . H51 H 0.5550 0.0631 0.3091 0.088(11) Uiso 1 1 calc R . . O51B O 0.47892(16) -0.03384(11) 0.21743(8) 0.0272(3) Uani 1 1 d . . . O58B O 0.48337(16) -0.80933(11) 0.14767(8) 0.0251(3) Uani 1 1 d . . . H58B H 0.4854 -0.8798 0.1699 0.038 Uiso 1 1 calc R . . O58A O 0.57174(18) -0.78810(12) 0.26121(8) 0.0323(4) Uani 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 C1 0.0196(10) 0.0149(8) 0.0182(9) -0.0011(7) -0.0048(7) -0.0038(7) C2 0.0179(9) 0.0177(9) 0.0198(9) 0.0026(7) -0.0018(7) -0.0039(7) C3 0.0192(10) 0.0180(9) 0.0208(9) 0.0032(7) -0.0022(7) -0.0044(7) C4 0.0193(10) 0.0186(9) 0.0225(10) 0.0036(8) -0.0010(8) -0.0041(7) C5 0.0189(9) 0.0176(9) 0.0203(9) 0.0022(7) -0.0022(7) -0.0045(7) C6 0.0192(9) 0.0170(9) 0.0210(9) 0.0020(7) -0.0012(7) -0.0040(7) C7 0.0168(9) 0.0159(9) 0.0187(9) 0.0002(7) -0.0017(7) -0.0037(7) C8 0.0183(9) 0.0126(8) 0.0171(9) -0.0003(7) -0.0030(7) -0.0032(7) O1A 0.0178(7) 0.0217(7) 0.0290(7) 0.0028(6) 0.0000(6) -0.0033(5) O1B 0.0180(7) 0.0164(6) 0.0287(7) 0.0064(6) 0.0000(6) -0.0037(5) O8A 0.0181(7) 0.0179(6) 0.0285(7) 0.0068(5) -0.0027(5) -0.0034(5) O8B 0.0160(7) 0.0180(6) 0.0301(7) 0.0017(5) -0.0026(5) -0.0040(5) C22 0.0200(10) 0.0214(9) 0.0213(10) -0.0003(8) -0.0016(8) -0.0048(8) C24 0.0211(10) 0.0197(9) 0.0232(10) -0.0023(8) -0.0012(8) -0.0017(8) C25 0.0237(10) 0.0209(9) 0.0256(10) -0.0025(8) -0.0022(8) -0.0070(8) N21 0.0149(8) 0.0257(8) 0.0235(8) -0.0014(7) -0.0014(6) -0.0044(7) N23 0.0171(8) 0.0206(8) 0.0218(8) 0.0010(6) -0.0026(6) -0.0054(6) C31 0.0174(9) 0.0134(8) 0.0182(9) -0.0008(7) -0.0021(7) -0.0038(7) C32 0.0159(9) 0.0172(9) 0.0191(9) 0.0003(7) -0.0006(7) -0.0059(7) C33 0.0183(9) 0.0161(9) 0.0225(10) 0.0025(7) -0.0020(7) -0.0044(7) C34 0.0184(9) 0.0164(9) 0.0204(9) 0.0022(7) -0.0017(7) -0.0042(7) C35 0.0188(10) 0.0186(9) 0.0227(10) 0.0033(8) -0.0012(8) -0.0041(7) C36 0.0197(10) 0.0163(9) 0.0207(9) 0.0011(7) -0.0001(7) -0.0044(7) C37 0.0185(10) 0.0193(9) 0.0235(10) 0.0016(8) -0.0018(8) -0.0047(8) C38 0.0192(10) 0.0148(8) 0.0174(9) -0.0008(7) -0.0035(7) -0.0040(7) O31A 0.0150(7) 0.0190(6) 0.0305(7) 0.0033(5) -0.0028(5) -0.0044(5) O31B 0.0178(7) 0.0172(6) 0.0280(7) 0.0063(5) -0.0041(5) -0.0038(5) O38A 0.0185(7) 0.0204(7) 0.0292(7) 0.0045(6) 0.0008(6) -0.0028(5) O38B 0.0189(7) 0.0170(6) 0.0277(7) 0.0063(6) 0.0002(6) -0.0027(5) C42 0.0196(10) 0.0190(9) 0.0232(10) -0.0023(8) -0.0009(8) -0.0029(8) C44 0.0199(10) 0.0180(9) 0.0231(10) -0.0025(8) -0.0019(8) -0.0028(7) C45 0.0215(10) 0.0195(9) 0.0247(10) -0.0023(8) -0.0013(8) -0.0060(8) N41 0.0139(8) 0.0237(8) 0.0224(8) -0.0011(7) -0.0011(6) -0.0050(6) N43 0.0155(8) 0.0202(8) 0.0232(8) 0.0006(6) -0.0022(6) -0.0054(6) C51 0.0178(9) 0.0188(9) 0.0249(10) -0.0059(8) -0.0011(8) -0.0028(7) C52 0.0200(10) 0.0182(9) 0.0212(9) -0.0016(7) -0.0013(7) -0.0030(7) C53 0.0242(10) 0.0166(9) 0.0242(10) -0.0009(8) -0.0018(8) -0.0057(8) C54 0.0207(10) 0.0186(9) 0.0236(10) -0.0011(8) -0.0006(8) -0.0074(7) C55 0.0175(9) 0.0190(9) 0.0247(10) -0.0011(8) -0.0012(7) -0.0055(7) C56 0.0179(9) 0.0178(9) 0.0291(10) 0.0005(8) -0.0024(8) -0.0050(7) C57 0.0217(10) 0.0186(9) 0.0247(10) -0.0007(8) 0.0016(8) -0.0063(8) C58 0.0186(10) 0.0200(9) 0.0245(10) -0.0049(8) 0.0003(8) -0.0027(7) O51A 0.0435(9) 0.0196(7) 0.0274(8) -0.0019(6) -0.0094(6) -0.0112(6) O51B 0.0377(8) 0.0204(7) 0.0255(8) -0.0009(6) -0.0065(6) -0.0096(6) O58B 0.0328(8) 0.0179(7) 0.0265(7) -0.0005(6) -0.0057(6) -0.0088(6) O58A 0.0520(10) 0.0208(7) 0.0278(8) 0.0009(6) -0.0125(7) -0.0125(6) _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 O1A 1.212(2) . ? C1 O1B 1.328(2) . ? C1 C2 1.508(2) . ? C2 C3 1.517(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.531(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.524(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.527(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.522(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.520(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O8B 1.249(2) . ? C8 O8A 1.277(2) . ? O1B H1 0.8400 . ? C22 N23 1.323(2) . ? C22 N21 1.326(2) . ? C22 H22 0.9500 . ? C24 C25 1.354(3) . ? C24 N23 1.379(2) . ? C24 H24 0.9500 . ? C25 N21 1.371(2) . ? C25 H25 0.9500 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? C31 O31A 1.246(2) . ? C31 O31B 1.278(2) . ? C31 C32 1.520(2) . ? C32 C33 1.519(2) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.528(2) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.524(2) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.528(2) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.520(2) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C38 1.504(2) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 O38A 1.216(2) . ? C38 O38B 1.326(2) . ? O38B H38 0.8400 . ? C42 N41 1.321(2) . ? C42 N43 1.327(2) . ? C42 H42 0.9500 . ? C44 C45 1.354(3) . ? C44 N43 1.374(2) . ? C44 H44 0.9500 . ? C45 N41 1.372(2) . ? C45 H45 0.9500 . ? N41 H41 0.8800 . ? N43 H43 0.8800 . ? C51 O51B 1.222(2) . ? C51 O51A 1.319(2) . ? C51 C52 1.502(2) . ? C52 C53 1.520(3) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 C54 1.526(2) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 C55 1.527(2) . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C55 C56 1.520(3) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 C57 1.527(3) . ? C56 H56B 0.9900 . ? C56 H56A 0.9900 . ? C57 C58 1.504(2) . ? C57 H57A 0.9900 . ? C57 H57B 0.9900 . ? C58 O58A 1.222(2) . ? C58 O58B 1.319(2) . ? O51A H51 0.8400 . ? O58B H58B 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 O1A C1 O1B 123.68(16) . . ? O1A C1 C2 124.93(15) . . ? O1B C1 C2 111.39(15) . . ? C1 C2 C3 115.38(15) . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2B 108.4 . . ? C3 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C4 111.22(14) . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 113.13(15) . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4B 109.0 . . ? C3 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C4 C5 C6 113.48(15) . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C7 C6 C5 111.86(15) . . ? C7 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? C7 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C6 116.36(14) . . ? C8 C7 H7A 108.2 . . ? C6 C7 H7A 108.2 . . ? C8 C7 H7B 108.2 . . ? C6 C7 H7B 108.2 . . ? H7A C7 H7B 107.4 . . ? O8B C8 O8A 123.37(15) . . ? O8B C8 C7 120.64(15) . . ? O8A C8 C7 115.98(15) . . ? C1 O1B H1 109.5 . . ? N23 C22 N21 108.62(16) . . ? N23 C22 H22 125.7 . . ? N21 C22 H22 125.7 . . ? C25 C24 N23 106.53(16) . . ? C25 C24 H24 126.7 . . ? N23 C24 H24 126.7 . . ? C24 C25 N21 107.19(16) . . ? C24 C25 H25 126.4 . . ? N21 C25 H25 126.4 . . ? C22 N21 C25 108.77(15) . . ? C22 N21 H21 125.6 . . ? C25 N21 H21 125.6 . . ? C22 N23 C24 108.88(15) . . ? C22 N23 H23 125.6 . . ? C24 N23 H23 125.6 . . ? O31A C31 O31B 123.46(15) . . ? O31A C31 C32 120.24(15) . . ? O31B C31 C32 116.29(15) . . ? C33 C32 C31 115.33(14) . . ? C33 C32 H32A 108.4 . . ? C31 C32 H32A 108.4 . . ? C33 C32 H32B 108.4 . . ? C31 C32 H32B 108.4 . . ? H32A C32 H32B 107.5 . . ? C32 C33 C34 112.73(14) . . ? C32 C33 H33A 109.0 . . ? C34 C33 H33A 109.0 . . ? C32 C33 H33B 109.0 . . ? C34 C33 H33B 109.0 . . ? H33A C33 H33B 107.8 . . ? C35 C34 C33 112.78(15) . . ? C35 C34 H34A 109.0 . . ? C33 C34 H34A 109.0 . . ? C35 C34 H34B 109.0 . . ? C33 C34 H34B 109.0 . . ? H34A C34 H34B 107.8 . . ? C34 C35 C36 113.80(15) . . ? C34 C35 H35A 108.8 . . ? C36 C35 H35A 108.8 . . ? C34 C35 H35B 108.8 . . ? C36 C35 H35B 108.8 . . ? H35A C35 H35B 107.7 . . ? C37 C36 C35 111.37(15) . . ? C37 C36 H36A 109.4 . . ? C35 C36 H36A 109.4 . . ? C37 C36 H36B 109.4 . . ? C35 C36 H36B 109.4 . . ? H36A C36 H36B 108.0 . . ? C38 C37 C36 115.08(15) . . ? C38 C37 H37A 108.5 . . ? C36 C37 H37A 108.5 . . ? C38 C37 H37B 108.5 . . ? C36 C37 H37B 108.5 . . ? H37A C37 H37B 107.5 . . ? O38A C38 O38B 123.34(15) . . ? O38A C38 C37 124.72(15) . . ? O38B C38 C37 111.93(15) . . ? C38 O38B H38 109.5 . . ? N41 C42 N43 108.74(16) . . ? N41 C42 H42 125.6 . . ? N43 C42 H42 125.6 . . ? C45 C44 N43 106.46(16) . . ? C45 C44 H44 126.8 . . ? N43 C44 H44 126.8 . . ? C44 C45 N41 107.35(16) . . ? C44 C45 H45 126.3 . . ? N41 C45 H45 126.3 . . ? C42 N41 C45 108.60(15) . . ? C42 N41 H41 125.7 . . ? C45 N41 H41 125.7 . . ? C42 N43 C44 108.85(15) . . ? C42 N43 H43 125.6 . . ? C44 N43 H43 125.6 . . ? O51B C51 O51A 123.20(16) . . ? O51B C51 C52 124.35(16) . . ? O51A C51 C52 112.43(16) . . ? C51 C52 C53 114.69(15) . . ? C51 C52 H52A 108.6 . . ? C53 C52 H52A 108.6 . . ? C51 C52 H52B 108.6 . . ? C53 C52 H52B 108.6 . . ? H52A C52 H52B 107.6 . . ? C52 C53 C54 111.21(15) . . ? C52 C53 H53A 109.4 . . ? C54 C53 H53A 109.4 . . ? C52 C53 H53B 109.4 . . ? C54 C53 H53B 109.4 . . ? H53A C53 H53B 108.0 . . ? C53 C54 C55 113.73(15) . . ? C53 C54 H54A 108.8 . . ? C55 C54 H54A 108.8 . . ? C53 C54 H54B 108.8 . . ? C55 C54 H54B 108.8 . . ? H54A C54 H54B 107.7 . . ? C56 C55 C54 113.03(15) . . ? C56 C55 H55A 109.0 . . ? C54 C55 H55A 109.0 . . ? C56 C55 H55B 109.0 . . ? C54 C55 H55B 109.0 . . ? H55A C55 H55B 107.8 . . ? C55 C56 C57 113.31(15) . . ? C55 C56 H56B 108.9 . . ? C57 C56 H56B 108.9 . . ? C55 C56 H56A 108.9 . . ? C57 C56 H56A 108.9 . . ? H56B C56 H56A 107.7 . . ? C58 C57 C56 114.33(15) . . ? C58 C57 H57A 108.7 . . ? C56 C57 H57A 108.7 . . ? C58 C57 H57B 108.7 . . ? C56 C57 H57B 108.7 . . ? H57A C57 H57B 107.6 . . ? O58A C58 O58B 123.30(17) . . ? O58A C58 C57 123.18(17) . . ? O58B C58 C57 113.49(16) . . ? C51 O51A H51 109.5 . . ? C58 O58B H58B 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 N23 H23 O8B 0.88 1.89 2.7356(19) 159.7 . N43 H43 O31A 0.88 1.86 2.7079(19) 160.2 . O1B H1 O31B 0.84 1.73 2.5648(17) 175.5 2_646 N21 H21 O8A 0.88 1.86 2.728(2) 168.2 1_655 O38B H38 O8A 0.84 1.71 2.5513(17) 175.2 2_665 N41 H41 O31B 0.88 1.81 2.6838(19) 169.9 1_455 O51A H51 O58A 0.84 1.81 2.6469(18) 176.0 1_565 O58B H58B O51B 0.84 1.84 2.6830(17) 176.9 1_545 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.309 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.057 #============================================================================== data_2 _database_code_depnum_ccdc_archive 'CCDC 745370' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Glutaric Acid and 1-Methylimidazole ; _chemical_name_common 'Glutaric Acid and 1-Methylimidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H28 N4 O8' _chemical_formula_weight 428.44 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 8.1285(6) _cell_length_b 9.1297(7) _cell_length_c 13.7387(11) _cell_angle_alpha 89.781(4) _cell_angle_beta 89.170(4) _cell_angle_gamma 79.782(5) _cell_volume 1003.28(13) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4427 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9889 _exptl_absorpt_correction_T_max 0.9955 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16423 _diffrn_reflns_av_R_equivalents 0.1160 _diffrn_reflns_av_sigmaI/netI 0.0909 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3525 _reflns_number_gt 2657 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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. ROTAX suggested merohedral twinning matrix -1 0 0 0 -1 0 0 0 1 which refined with a BASF parameter of 0.17826 and reducing the R values (R1 obsd from 13.81% to 7.00%). ; _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^)+(0.0553P)^2^+1.9881P] 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_extinction_coef ? _refine_ls_number_reflns 3525 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1001 _refine_ls_R_factor_gt 0.0700 _refine_ls_wR_factor_ref 0.1682 _refine_ls_wR_factor_gt 0.1521 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 C1 C 0.6757(5) 0.5557(5) 0.8046(3) 0.0246(10) Uani 1 1 d . . . C2 C 0.5982(5) 0.6323(5) 0.7141(3) 0.0253(10) Uani 1 1 d . . . H2A H 0.5994 0.7402 0.7199 0.030 Uiso 1 1 calc R . . H2B H 0.4797 0.6199 0.7123 0.030 Uiso 1 1 calc R . . C3 C 0.6809(5) 0.5785(5) 0.6182(3) 0.0224(9) Uani 1 1 d . . . H3A H 0.6745 0.4722 0.6091 0.027 Uiso 1 1 calc R . . H3B H 0.8003 0.5878 0.6191 0.027 Uiso 1 1 calc R . . C4 C 0.5950(5) 0.6695(5) 0.5338(3) 0.0263(10) Uani 1 1 d . . . H4A H 0.4735 0.6689 0.5387 0.032 Uiso 1 1 calc R . . H4B H 0.6110 0.7739 0.5411 0.032 Uiso 1 1 calc R . . C5 C 0.6557(5) 0.6162(5) 0.4336(3) 0.0249(10) Uani 1 1 d . . . O1A O 0.6089(4) 0.6081(3) 0.8877(2) 0.0309(8) Uani 1 1 d . . . H1 H 0.5341 0.6824 0.8773 0.046 Uiso 1 1 calc R . . O1B O 0.7901(4) 0.4500(3) 0.8015(2) 0.0295(7) Uani 1 1 d . . . O5A O 0.7648(4) 0.5068(3) 0.4205(2) 0.0314(8) Uani 1 1 d . . . O5B O 0.5864(4) 0.6920(3) 0.3599(2) 0.0308(8) Uani 1 1 d . . . H5 H 0.5095 0.7594 0.3800 0.046 Uiso 1 1 calc R . . C22 C 1.0503(5) 0.1834(5) 0.6949(3) 0.0262(10) Uani 1 1 d . . . H22 H 0.9768 0.2625 0.7260 0.031 Uiso 1 1 calc R . . C24 C 1.2390(6) -0.0161(5) 0.6709(3) 0.0325(11) Uani 1 1 d . . . H24 H 1.3216 -0.1016 0.6827 0.039 Uiso 1 1 calc R . . C25 C 1.1839(6) 0.0380(5) 0.5840(3) 0.0288(10) Uani 1 1 d . . . H25 H 1.2206 -0.0039 0.5225 0.035 Uiso 1 1 calc R . . C26 C 0.9744(6) 0.2554(5) 0.5245(3) 0.0345(12) Uani 1 1 d . . . H26A H 0.8558 0.2483 0.5297 0.052 Uiso 1 1 calc R . . H26B H 1.0175 0.2217 0.4599 0.052 Uiso 1 1 calc R . . H26C H 0.9876 0.3590 0.5339 0.052 Uiso 1 1 calc R . . N21 N 1.0669(5) 0.1626(4) 0.5984(3) 0.0282(9) Uani 1 1 d . . . N23 N 1.1515(5) 0.0776(4) 0.7396(3) 0.0283(9) Uani 1 1 d . . . H23 H 1.1619 0.0678 0.8031 0.061(19) Uiso 1 1 calc R . . C31 C 0.3182(5) 0.9110(5) 0.9345(3) 0.0223(9) Uani 1 1 d . . . C32 C 0.3769(5) 0.8597(5) 1.0357(3) 0.0229(9) Uani 1 1 d . . . H32A H 0.3603 0.7556 1.0442 0.028 Uiso 1 1 calc R . . H32B H 0.4985 0.8595 1.0387 0.028 Uiso 1 1 calc R . . C33 C 0.2930(5) 0.9499(5) 1.1207(3) 0.0250(10) Uani 1 1 d . . . H33A H 0.1719 0.9468 1.1215 0.030 Uiso 1 1 calc R . . H33B H 0.3067 1.0550 1.1133 0.030 Uiso 1 1 calc R . . C34 C 0.3695(5) 0.8880(5) 1.2161(3) 0.0241(10) Uani 1 1 d . . . H34A H 0.3589 0.7818 1.2205 0.029 Uiso 1 1 calc R . . H34B H 0.4904 0.8922 1.2136 0.029 Uiso 1 1 calc R . . C35 C 0.2964(5) 0.9646(5) 1.3080(3) 0.0239(10) Uani 1 1 d . . . O31A O 0.3807(4) 0.8322(3) 0.8635(2) 0.0277(7) Uani 1 1 d . . . O31B O 0.2128(4) 1.0278(3) 0.9263(2) 0.0275(7) Uani 1 1 d . . . O35A O 0.3572(4) 0.9075(3) 1.3878(2) 0.0310(8) Uani 1 1 d . . . O35B O 0.1842(4) 1.0763(3) 1.3066(2) 0.0260(7) Uani 1 1 d . . . C42 C -0.1001(5) 1.3776(5) 1.2070(3) 0.0268(10) Uani 1 1 d . . . H42 H -0.1214 1.4047 1.2732 0.032 Uiso 1 1 calc R . . C44 C -0.0023(5) 1.2568(5) 1.0748(3) 0.0267(10) Uani 1 1 d . . . H44 H 0.0582 1.1832 1.0328 0.032 Uiso 1 1 calc R . . C45 C -0.1076(5) 1.3794(5) 1.0482(3) 0.0294(11) Uani 1 1 d . . . H45 H -0.1356 1.4091 0.9833 0.035 Uiso 1 1 calc R . . C46 C -0.2849(6) 1.5957(5) 1.1341(4) 0.0346(11) Uani 1 1 d . . . H46A H -0.2319 1.6741 1.1049 0.052 Uiso 1 1 calc R . . H46B H -0.3159 1.6213 1.2019 0.052 Uiso 1 1 calc R . . H46C H -0.3853 1.5866 1.0977 0.052 Uiso 1 1 calc R . . N41 N -0.1682(4) 1.4547(4) 1.1309(3) 0.0272(9) Uani 1 1 d . . . N43 N 0.0015(4) 1.2580(4) 1.1760(3) 0.0269(9) Uani 1 1 d . . . H43 H 0.0615 1.1903 1.2129 0.032 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 0.029(2) 0.025(2) 0.019(2) -0.0051(19) -0.0014(19) -0.003(2) C2 0.029(2) 0.025(2) 0.020(2) -0.0030(18) -0.0006(18) -0.0007(19) C3 0.029(2) 0.021(2) 0.016(2) -0.0007(17) -0.0028(18) -0.0030(18) C4 0.029(2) 0.023(2) 0.025(3) 0.0010(19) -0.0018(19) -0.0006(19) C5 0.030(2) 0.026(2) 0.019(2) -0.0011(19) -0.0061(19) -0.004(2) O1A 0.0402(19) 0.0295(18) 0.0186(16) -0.0008(13) -0.0012(14) 0.0053(14) O1B 0.0353(18) 0.0258(17) 0.0241(17) 0.0000(13) -0.0015(14) 0.0035(15) O5A 0.0385(18) 0.0287(17) 0.0218(17) -0.0017(13) -0.0002(13) 0.0082(15) O5B 0.0382(19) 0.0303(17) 0.0193(17) -0.0005(14) 0.0011(13) 0.0061(14) C22 0.027(2) 0.029(2) 0.022(2) -0.006(2) -0.0011(19) -0.005(2) C24 0.038(3) 0.030(2) 0.029(3) -0.001(2) -0.003(2) -0.004(2) C25 0.031(2) 0.029(2) 0.026(2) 0.000(2) -0.0013(19) -0.004(2) C26 0.039(3) 0.032(3) 0.031(3) 0.004(2) -0.005(2) -0.003(2) N21 0.033(2) 0.027(2) 0.024(2) 0.0028(16) -0.0045(16) -0.0051(17) N23 0.032(2) 0.031(2) 0.022(2) -0.0013(17) -0.0039(16) -0.0047(17) C31 0.026(2) 0.023(2) 0.018(2) -0.0042(18) -0.0028(18) -0.0043(19) C32 0.027(2) 0.022(2) 0.019(2) 0.0017(18) -0.0003(18) -0.0026(18) C33 0.032(2) 0.026(2) 0.015(2) -0.0024(18) -0.0011(19) 0.0005(19) C34 0.028(2) 0.022(2) 0.021(2) 0.0015(18) 0.0001(18) -0.0001(19) C35 0.028(2) 0.027(2) 0.019(2) 0.0026(19) -0.0003(19) -0.010(2) O31A 0.0342(17) 0.0265(16) 0.0200(16) -0.0006(13) 0.0030(13) 0.0012(14) O31B 0.0332(17) 0.0272(17) 0.0193(16) 0.0012(13) -0.0023(13) 0.0028(14) O35A 0.0424(18) 0.0347(18) 0.0114(15) 0.0025(13) -0.0013(14) 0.0052(15) O35B 0.0310(16) 0.0240(16) 0.0188(16) -0.0015(13) -0.0013(13) 0.0071(14) C42 0.033(2) 0.028(2) 0.021(2) 0.002(2) -0.0014(19) -0.010(2) C44 0.034(3) 0.024(2) 0.022(2) -0.0012(19) 0.0016(19) -0.003(2) C45 0.034(3) 0.025(2) 0.028(3) -0.006(2) 0.006(2) -0.002(2) C46 0.033(3) 0.026(2) 0.042(3) -0.003(2) 0.004(2) 0.002(2) N41 0.032(2) 0.024(2) 0.025(2) 0.0015(16) -0.0022(17) -0.0042(17) N43 0.032(2) 0.025(2) 0.022(2) 0.0031(15) -0.0018(16) 0.0004(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1B 1.216(5) . ? C1 O1A 1.312(5) . ? C1 C2 1.514(6) . ? C2 C3 1.514(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.527(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.509(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O5A 1.224(5) . ? C5 O5B 1.301(5) . ? O1A H1 0.8400 . ? O5B H5 0.8400 . ? C22 N23 1.310(5) . ? C22 N21 1.342(6) . ? C22 H22 0.9500 . ? C24 C25 1.343(6) . ? C24 N23 1.378(6) . ? C24 H24 0.9500 . ? C25 N21 1.360(6) . ? C25 H25 0.9500 . ? C26 N21 1.451(6) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N23 H23 0.8800 . ? C31 O31B 1.250(5) . ? C31 O31A 1.260(5) . ? C31 C32 1.521(6) . ? C32 C33 1.514(6) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.523(6) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.508(6) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 O35B 1.242(5) . ? C35 O35A 1.280(5) . ? C42 N43 1.315(5) . ? C42 N41 1.329(6) . ? C42 H42 0.9500 . ? C44 C45 1.336(6) . ? C44 N43 1.391(6) . ? C44 H44 0.9500 . ? C45 N41 1.369(6) . ? C45 H45 0.9500 . ? C46 N41 1.458(5) . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? N43 H43 0.8800 . ? 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 O1B C1 O1A 121.4(4) . . ? O1B C1 C2 122.8(4) . . ? O1A C1 C2 115.8(3) . . ? C1 C2 C3 116.1(3) . . ? C1 C2 H2A 108.3 . . ? C3 C2 H2A 108.3 . . ? C1 C2 H2B 108.3 . . ? C3 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? C2 C3 C4 110.5(3) . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C3 115.3(3) . . ? C5 C4 H4A 108.4 . . ? C3 C4 H4A 108.4 . . ? C5 C4 H4B 108.4 . . ? C3 C4 H4B 108.4 . . ? H4A C4 H4B 107.5 . . ? O5A C5 O5B 120.5(4) . . ? O5A C5 C4 122.5(4) . . ? O5B C5 C4 117.0(4) . . ? C1 O1A H1 109.5 . . ? C5 O5B H5 109.5 . . ? N23 C22 N21 109.3(4) . . ? N23 C22 H22 125.4 . . ? N21 C22 H22 125.4 . . ? C25 C24 N23 106.1(4) . . ? C25 C24 H24 127.0 . . ? N23 C24 H24 127.0 . . ? C24 C25 N21 108.7(4) . . ? C24 C25 H25 125.6 . . ? N21 C25 H25 125.6 . . ? N21 C26 H26A 109.5 . . ? N21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 N21 C25 107.1(4) . . ? C22 N21 C26 125.8(4) . . ? C25 N21 C26 127.1(4) . . ? C22 N23 C24 108.8(4) . . ? C22 N23 H23 125.6 . . ? C24 N23 H23 125.6 . . ? O31B C31 O31A 123.9(4) . . ? O31B C31 C32 118.8(4) . . ? O31A C31 C32 117.3(3) . . ? C33 C32 C31 116.7(3) . . ? C33 C32 H32A 108.1 . . ? C31 C32 H32A 108.1 . . ? C33 C32 H32B 108.1 . . ? C31 C32 H32B 108.1 . . ? H32A C32 H32B 107.3 . . ? C32 C33 C34 110.3(3) . . ? C32 C33 H33A 109.6 . . ? C34 C33 H33A 109.6 . . ? C32 C33 H33B 109.6 . . ? C34 C33 H33B 109.6 . . ? H33A C33 H33B 108.1 . . ? C35 C34 C33 116.6(3) . . ? C35 C34 H34A 108.1 . . ? C33 C34 H34A 108.1 . . ? C35 C34 H34B 108.1 . . ? C33 C34 H34B 108.1 . . ? H34A C34 H34B 107.3 . . ? O35B C35 O35A 121.9(4) . . ? O35B C35 C34 122.2(4) . . ? O35A C35 C34 115.9(4) . . ? N43 C42 N41 109.3(4) . . ? N43 C42 H42 125.4 . . ? N41 C42 H42 125.4 . . ? C45 C44 N43 106.5(4) . . ? C45 C44 H44 126.7 . . ? N43 C44 H44 126.7 . . ? C44 C45 N41 108.1(4) . . ? C44 C45 H45 126.0 . . ? N41 C45 H45 126.0 . . ? N41 C46 H46A 109.5 . . ? N41 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? N41 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C42 N41 C45 107.9(4) . . ? C42 N41 C46 126.4(4) . . ? C45 N41 C46 125.7(4) . . ? C42 N43 C44 108.2(4) . . ? C42 N43 H43 125.9 . . ? C44 N43 H43 125.9 . . ? 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 O1A H1 O31A 0.84 1.69 2.531(4) 176.5 . N43 H43 O35B 0.88 1.84 2.713(4) 169.5 . N23 H23 O31B 0.88 1.77 2.642(5) 170.7 1_645 O5B H5 O35A 0.84 1.67 2.484(4) 164.1 1_554 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.510 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.065 #============================================================================== data_3 _database_code_depnum_ccdc_archive 'CCDC 745372' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Succinic acid & 4-methylimidazole ; _chemical_name_common 'Succinic acid & 4-methylimidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 N2 O4' _chemical_formula_weight 200.20 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_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.9015(2) _cell_length_b 17.3293(10) _cell_length_c 13.8628(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.299(3) _cell_angle_gamma 90.00 _cell_volume 931.61(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2165 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9886 _exptl_absorpt_correction_T_max 0.9931 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9780 _diffrn_reflns_av_R_equivalents 0.0718 _diffrn_reflns_av_sigmaI/netI 0.0599 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2117 _reflns_number_gt 1562 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^)+(0.0425P)^2^+0.4542P] 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_extinction_coef ? _refine_ls_number_reflns 2117 _refine_ls_number_parameters 132 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.1057 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 C1 C 0.2363(5) -0.03345(11) 0.88098(12) 0.0200(4) Uani 1 1 d . . . C2 C 0.4277(5) 0.02003(11) 0.95350(12) 0.0210(4) Uani 1 1 d . . . H2A H 0.2697 0.0616 0.9696 0.025 Uiso 1 1 calc R . . H2B H 0.6198 0.0443 0.9235 0.025 Uiso 1 1 calc R . . O1A O 0.1840(4) -0.10088(8) 0.89667(10) 0.0320(4) Uani 1 1 d . . . O1B O 0.1261(4) 0.00217(8) 0.79940(9) 0.0280(3) Uani 1 1 d . . . H1 H 0.0259 -0.0296 0.7602 0.058(8) Uiso 1 1 calc R . . C22 C 0.3031(5) 0.25873(11) 0.67050(13) 0.0239(4) Uani 1 1 d . . . H22 H 0.1675 0.2901 0.6248 0.029 Uiso 1 1 calc R . . C24 C 0.6037(5) 0.21833(11) 0.80502(13) 0.0206(4) Uani 1 1 d . . . C25 C 0.6007(5) 0.16166(11) 0.73784(13) 0.0227(4) Uani 1 1 d . . . H25 H 0.7090 0.1127 0.7466 0.027 Uiso 1 1 calc R . . C26 C 0.7673(5) 0.22233(12) 0.90688(13) 0.0257(4) Uani 1 1 d . . . H26A H 0.5878 0.2233 0.9511 0.039 Uiso 1 1 calc R . . H26B H 0.9072 0.2693 0.9158 0.039 Uiso 1 1 calc R . . H26C H 0.9147 0.1770 0.9210 0.039 Uiso 1 1 calc R . . N21 N 0.4121(4) 0.18790(9) 0.65438(11) 0.0230(4) Uani 1 1 d . . . H21 H 0.3709 0.1620 0.5997 0.042(7) Uiso 1 1 calc R . . N23 N 0.4144(4) 0.27849(9) 0.76064(11) 0.0213(4) Uani 1 1 d . . . H23 H 0.3744 0.3229 0.7880 0.047(7) Uiso 1 1 calc R . . C31 C 0.1884(5) 0.42356(10) 0.91659(12) 0.0183(4) Uani 1 1 d . . . C32 C 0.0245(5) 0.49764(10) 0.94629(12) 0.0188(4) Uani 1 1 d . . . H32B H -0.2033 0.5033 0.9078 0.023 Uiso 1 1 calc R . . H32A H 0.1698 0.5415 0.9299 0.023 Uiso 1 1 calc R . . O31B O 0.3141(3) 0.37607(7) 0.97756(9) 0.0249(3) Uani 1 1 d . . . O31A O 0.1961(3) 0.41353(8) 0.82538(9) 0.0256(3) Uani 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 C1 0.0200(9) 0.0219(10) 0.0180(9) 0.0001(7) 0.0017(7) 0.0018(8) C2 0.0221(9) 0.0216(10) 0.0188(9) -0.0014(7) 0.0008(7) -0.0006(7) O1A 0.0453(9) 0.0237(8) 0.0245(7) 0.0015(6) -0.0073(6) -0.0094(7) O1B 0.0402(8) 0.0231(7) 0.0185(7) 0.0008(6) -0.0066(6) -0.0041(6) C22 0.0291(10) 0.0230(10) 0.0195(9) -0.0005(8) 0.0026(7) 0.0008(8) C24 0.0215(9) 0.0193(10) 0.0210(9) 0.0020(7) 0.0026(7) -0.0007(8) C25 0.0270(10) 0.0187(10) 0.0222(9) 0.0012(7) 0.0026(7) 0.0037(8) C26 0.0274(10) 0.0256(11) 0.0232(10) -0.0007(8) -0.0012(8) -0.0002(8) N21 0.0297(9) 0.0211(8) 0.0179(8) -0.0029(7) 0.0017(6) 0.0010(7) N23 0.0271(8) 0.0179(8) 0.0192(8) -0.0018(6) 0.0033(6) 0.0019(7) C31 0.0197(9) 0.0177(9) 0.0170(9) -0.0011(7) -0.0003(7) -0.0031(7) C32 0.0217(9) 0.0178(9) 0.0167(9) 0.0005(7) 0.0012(7) 0.0016(7) O31B 0.0334(8) 0.0216(7) 0.0187(7) 0.0022(5) -0.0010(5) 0.0048(6) O31A 0.0372(8) 0.0248(7) 0.0140(6) -0.0020(5) -0.0010(5) 0.0100(6) _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 O1A 1.210(2) . ? C1 O1B 1.318(2) . ? C1 C2 1.504(3) . ? C2 C2 1.517(3) 3_657 ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? O1B H1 0.8400 . ? C22 N23 1.322(2) . ? C22 N21 1.326(2) . ? C22 H22 0.9500 . ? C24 C25 1.353(3) . ? C24 N23 1.382(2) . ? C24 C26 1.486(3) . ? C25 N21 1.379(2) . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? C31 O31B 1.241(2) . ? C31 O31A 1.280(2) . ? C31 C32 1.511(2) . ? C32 C32 1.524(3) 3_567 ? C32 H32B 0.9900 . ? C32 H32A 0.9900 . ? 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 O1A C1 O1B 124.11(17) . . ? O1A C1 C2 123.78(16) . . ? O1B C1 C2 112.10(16) . . ? C1 C2 C2 113.39(19) . 3_657 ? C1 C2 H2A 108.9 . . ? C2 C2 H2A 108.9 3_657 . ? C1 C2 H2B 108.9 . . ? C2 C2 H2B 108.9 3_657 . ? H2A C2 H2B 107.7 . . ? C1 O1B H1 109.5 . . ? N23 C22 N21 108.73(17) . . ? N23 C22 H22 125.6 . . ? N21 C22 H22 125.6 . . ? C25 C24 N23 106.10(16) . . ? C25 C24 C26 131.18(18) . . ? N23 C24 C26 122.72(16) . . ? C24 C25 N21 107.57(16) . . ? C24 C25 H25 126.2 . . ? N21 C25 H25 126.2 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 N21 C25 108.38(15) . . ? C22 N21 H21 125.8 . . ? C25 N21 H21 125.8 . . ? C22 N23 C24 109.23(16) . . ? C22 N23 H23 125.4 . . ? C24 N23 H23 125.4 . . ? O31B C31 O31A 122.16(16) . . ? O31B C31 C32 121.67(15) . . ? O31A C31 C32 116.16(15) . . ? C31 C32 C32 114.44(19) . 3_567 ? C31 C32 H32B 108.6 . . ? C32 C32 H32B 108.6 3_567 . ? C31 C32 H32A 108.6 . . ? C32 C32 H32A 108.6 3_567 . ? H32B C32 H32A 107.6 . . ? 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 N23 H23 O31A 0.88 1.82 2.679(2) 166.3 . O1B H1 O31A 0.84 1.70 2.5406(18) 174.3 2_546 N21 H21 O31B 0.88 1.81 2.679(2) 169.9 4_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.215 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.057 #============================================================================== data_4 _database_code_depnum_ccdc_archive 'CCDC 745373' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Glutaric acid & 2-methylimidazole ; _chemical_name_common 'Glutaric acid & 2-methylimidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H14 N2 O4' _chemical_formula_weight 214.22 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 5.3800(3) _cell_length_b 8.1542(6) _cell_length_c 12.6592(10) _cell_angle_alpha 78.350(4) _cell_angle_beta 82.962(4) _cell_angle_gamma 84.496(4) _cell_volume 538.37(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2447 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 228 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9855 _exptl_absorpt_correction_T_max 0.9979 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10916 _diffrn_reflns_av_R_equivalents 0.1466 _diffrn_reflns_av_sigmaI/netI 0.1080 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1891 _reflns_number_gt 1320 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0224P)^2^+0.6573P] 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_extinction_coef ? _refine_ls_number_reflns 1891 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1262 _refine_ls_R_factor_gt 0.0851 _refine_ls_wR_factor_ref 0.1543 _refine_ls_wR_factor_gt 0.1380 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.003 _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 C1 C -0.3361(6) 0.3332(4) 0.4027(3) 0.0252(8) Uani 1 1 d . . . C2 C -0.1155(6) 0.2119(4) 0.3784(3) 0.0282(8) Uani 1 1 d . . . H2A H -0.1502 0.0982 0.4196 0.034 Uiso 1 1 calc R . . H2B H 0.0353 0.2451 0.4041 0.034 Uiso 1 1 calc R . . C3 C -0.0588(6) 0.2044(4) 0.2589(3) 0.0237(8) Uani 1 1 d . . . H3A H -0.0536 0.3201 0.2160 0.028 Uiso 1 1 calc R . . H3B H -0.1955 0.1509 0.2360 0.028 Uiso 1 1 calc R . . C4 C 0.1896(6) 0.1064(4) 0.2353(3) 0.0248(8) Uani 1 1 d . . . H4A H 0.3240 0.1571 0.2618 0.030 Uiso 1 1 calc R . . H4B H 0.1807 -0.0102 0.2765 0.030 Uiso 1 1 calc R . . C5 C 0.2604(6) 0.1012(4) 0.1169(3) 0.0246(8) Uani 1 1 d . . . O1A O -0.3417(4) 0.3823(3) 0.49380(19) 0.0298(6) Uani 1 1 d . . . H1 H -0.4490 0.4639 0.4956 0.03(2) Uiso 0.50 1 calc PR . . O1B O -0.4922(4) 0.3798(3) 0.3383(2) 0.0341(7) Uani 1 1 d . . . O5A O 0.4420(5) -0.0071(3) 0.0971(2) 0.0332(7) Uani 1 1 d . . . H5 H 0.4704 -0.0022 0.0298 0.08(3) Uiso 0.50 1 calc PR . . O5B O 0.1523(4) 0.1976(3) 0.0465(2) 0.0356(7) Uani 1 1 d . . . C22 C 1.1177(6) -0.3466(4) 0.1818(3) 0.0267(8) Uani 1 1 d . . . C24 C 0.7833(6) -0.2257(4) 0.2631(3) 0.0261(8) Uani 1 1 d . . . H24 H 0.6273 -0.1630 0.2740 0.031 Uiso 1 1 calc R . . C25 C 0.9269(6) -0.3058(4) 0.3406(3) 0.0279(8) Uani 1 1 d . . . H25 H 0.8924 -0.3107 0.4166 0.034 Uiso 1 1 calc R . . C26 C 1.2996(6) -0.4045(5) 0.0974(3) 0.0326(9) Uani 1 1 d . . . H26A H 1.4513 -0.4571 0.1297 0.049 Uiso 1 1 calc R . . H26B H 1.3437 -0.3085 0.0401 0.049 Uiso 1 1 calc R . . H26C H 1.2244 -0.4865 0.0664 0.049 Uiso 1 1 calc R . . N21 N 1.1348(5) -0.3795(3) 0.2874(2) 0.0271(7) Uani 1 1 d . . . H21 H 1.2596 -0.4393 0.3191 0.095(19) Uiso 1 1 calc R . . N23 N 0.9052(5) -0.2518(3) 0.1654(2) 0.0266(7) Uani 1 1 d . . . H23 H 0.8510 -0.2120 0.1017 0.078(17) 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 0.0234(18) 0.0273(19) 0.025(2) -0.0071(16) -0.0043(15) 0.0031(14) C2 0.0263(18) 0.0309(19) 0.027(2) -0.0074(16) -0.0028(15) 0.0067(15) C3 0.0230(17) 0.0264(18) 0.0224(19) -0.0066(15) -0.0067(14) 0.0041(14) C4 0.0230(17) 0.0274(18) 0.024(2) -0.0066(15) -0.0043(15) 0.0037(14) C5 0.0215(17) 0.0269(18) 0.027(2) -0.0101(16) -0.0049(15) 0.0005(15) O1A 0.0293(13) 0.0391(15) 0.0210(14) -0.0125(11) -0.0047(10) 0.0151(11) O1B 0.0295(13) 0.0423(15) 0.0359(16) -0.0220(12) -0.0143(12) 0.0158(11) O5A 0.0358(14) 0.0393(15) 0.0221(16) -0.0100(12) -0.0025(12) 0.0175(12) O5B 0.0381(14) 0.0417(15) 0.0225(15) -0.0055(12) -0.0049(11) 0.0197(12) C22 0.0236(18) 0.0284(19) 0.029(2) -0.0055(16) -0.0059(15) 0.0005(15) C24 0.0228(17) 0.0302(19) 0.025(2) -0.0060(16) -0.0006(15) 0.0000(15) C25 0.0289(18) 0.0289(19) 0.025(2) -0.0049(16) -0.0015(15) 0.0028(15) C26 0.0279(18) 0.039(2) 0.031(2) -0.0123(17) 0.0008(16) 0.0042(16) N21 0.0250(15) 0.0280(16) 0.0277(18) -0.0041(13) -0.0069(13) 0.0034(13) N23 0.0248(15) 0.0329(16) 0.0210(18) -0.0026(13) -0.0061(13) 0.0027(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1B 1.223(4) . ? C1 O1A 1.291(4) . ? C1 C2 1.513(4) . ? C2 C3 1.518(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.519(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.509(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O5B 1.227(4) . ? C5 O5A 1.289(4) . ? O1A H1 0.8400 . ? O5A H5 0.8400 . ? C22 N21 1.322(4) . ? C22 N23 1.331(4) . ? C22 C26 1.477(5) . ? C24 C25 1.348(5) . ? C24 N23 1.374(4) . ? C24 H24 0.9500 . ? C25 N21 1.384(4) . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? 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 O1B C1 O1A 124.2(3) . . ? O1B C1 C2 120.8(3) . . ? O1A C1 C2 115.0(3) . . ? C1 C2 C3 113.8(3) . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2B 108.8 . . ? C3 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C2 C3 C4 112.1(3) . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 114.3(3) . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4A 108.7 . . ? C5 C4 H4B 108.7 . . ? C3 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? O5B C5 O5A 124.1(3) . . ? O5B C5 C4 120.7(3) . . ? O5A C5 C4 115.2(3) . . ? C1 O1A H1 109.5 . . ? C5 O5A H5 109.5 . . ? N21 C22 N23 107.3(3) . . ? N21 C22 C26 126.5(3) . . ? N23 C22 C26 126.2(3) . . ? C25 C24 N23 107.0(3) . . ? C25 C24 H24 126.5 . . ? N23 C24 H24 126.5 . . ? C24 C25 N21 106.2(3) . . ? C24 C25 H25 126.9 . . ? N21 C25 H25 126.9 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 N21 C25 109.8(3) . . ? C22 N21 H21 125.1 . . ? C25 N21 H21 125.1 . . ? C22 N23 C24 109.6(3) . . ? C22 N23 H23 125.2 . . ? C24 N23 H23 125.2 . . ? 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 N23 H23 O5A 0.88 2.63 3.133(3) 117.2 . O1A H1 O1A 0.84 1.62 2.457(4) 176.8 2_466 O1A H1 O1B 0.84 2.64 3.153(3) 120.5 2_466 O5A H5 O5A 0.84 1.61 2.442(5) 173.5 2_655 N23 H23 O5B 0.88 1.86 2.681(4) 154.8 2_655 N21 H21 O1B 0.88 1.89 2.710(3) 154.3 1_745 N21 H21 O1A 0.88 2.60 3.104(4) 117.3 2_656 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.212 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.058 #============================================================================== data_5 _database_code_depnum_ccdc_archive 'CCDC 745374' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Adipic Acid and 2-Methylimidazole ; _chemical_name_common 'Adipic Acid and 2-Methylimidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H18 N2 O5' _chemical_formula_weight 246.26 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 4.8629(3) _cell_length_b 7.9978(5) _cell_length_c 16.5263(11) _cell_angle_alpha 96.9510(10) _cell_angle_beta 94.4750(10) _cell_angle_gamma 107.3840(10) _cell_volume 604.44(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3399 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 28.64 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.109 _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 120(2) _diffrn_radiation_wavelength 0.67100 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 5294 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.83 _reflns_number_total 2668 _reflns_number_gt 2332 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ? _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. Due to the very small size and weakly diffracting nature of the crystals, data could only be collected using synchrotron radiation. Even doing so, the completeness of the data is slightly reduced due to the weak diffraction. In spite of this the data is still fine for structural analysis. ; _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^)+(0.0940P)^2^+0.1815P] 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 2668 _refine_ls_number_parameters 164 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0578 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1518 _refine_ls_wR_factor_gt 0.1450 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.001 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 0.7807(3) 0.40570(18) 0.33759(8) 0.0162(3) Uani 1 1 d . . . C2 C 0.6430(3) 0.51297(18) 0.39390(8) 0.0183(3) Uani 1 1 d . . . H2A H 0.4646 0.5201 0.3633 0.022 Uiso 1 1 calc R . . H2B H 0.7785 0.6351 0.4084 0.022 Uiso 1 1 calc R . . C3 C 0.5643(3) 0.44048(18) 0.47293(8) 0.0170(3) Uani 1 1 d . . . H3A H 0.7404 0.4306 0.5037 0.020 Uiso 1 1 calc R . . H3B H 0.4220 0.3202 0.4593 0.020 Uiso 1 1 calc R . . O1A O 0.8633(2) 0.28434(13) 0.36149(6) 0.0204(3) Uani 1 1 d . . . O1B O 0.8110(2) 0.44532(14) 0.26536(6) 0.0234(3) Uani 1 1 d . . . C22 C 0.7542(3) 0.98177(18) -0.23857(9) 0.0189(3) Uani 1 1 d . . . C24 C 0.8726(3) 0.7967(2) -0.16393(9) 0.0224(3) Uani 1 1 d . . . H24 H 0.9490 0.7077 -0.1480 0.027 Uiso 1 1 calc R . . C25 C 0.7328(3) 0.88781(19) -0.11764(9) 0.0209(3) Uani 1 1 d . . . H25 H 0.6923 0.8757 -0.0630 0.025 Uiso 1 1 calc R . . C26 C 0.7221(4) 1.0795(2) -0.30718(9) 0.0263(4) Uani 1 1 d . . . H26A H 0.8643 1.0704 -0.3450 0.039 Uiso 1 1 calc R . . H26B H 0.7551 1.2044 -0.2856 0.039 Uiso 1 1 calc R . . H26C H 0.5257 1.0284 -0.3365 0.039 Uiso 1 1 calc R . . N21 N 0.6602(3) 1.00225(16) -0.16545(7) 0.0189(3) Uani 1 1 d . . . H21 H 0.5664 1.0770 -0.1500 0.023 Uiso 1 1 calc R . . N23 N 0.8838(3) 0.85711(16) -0.23859(8) 0.0204(3) Uani 1 1 d . . . H23 H 0.9642 0.8190 -0.2799 0.024 Uiso 1 1 calc R . . C31 C 0.6964(3) 0.68074(17) 0.13570(8) 0.0152(3) Uani 1 1 d . . . C32 C 0.8589(3) 0.55855(17) 0.10181(8) 0.0151(3) Uani 1 1 d . . . H32A H 0.7407 0.4349 0.1037 0.018 Uiso 1 1 calc R . . H32B H 1.0417 0.5832 0.1386 0.018 Uiso 1 1 calc R . . C33 C 0.9332(3) 0.57173(17) 0.01498(8) 0.0152(3) Uani 1 1 d . . . H33A H 1.0721 0.6901 0.0133 0.018 Uiso 1 1 calc R . . H33B H 0.7551 0.5582 -0.0220 0.018 Uiso 1 1 calc R . . O31A O 0.6259(2) 0.66800(14) 0.20946(6) 0.0216(3) Uani 1 1 d . . . H31 H 0.6996 0.5979 0.2300 0.032 Uiso 1 1 calc R . . O31B O 0.6303(2) 0.78561(13) 0.09505(6) 0.0187(3) Uani 1 1 d . . . O1W O 0.7897(3) 0.0793(2) 0.49132(9) 0.0400(4) Uani 1 1 d D . . H1W H 0.827(11) -0.009(4) 0.473(3) 0.19(2) Uiso 1 1 d D . . H2W H 0.808(5) 0.151(3) 0.4576(13) 0.050(7) 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 0.0182(6) 0.0184(6) 0.0135(6) 0.0018(5) 0.0050(5) 0.0076(5) C2 0.0258(7) 0.0203(7) 0.0149(6) 0.0041(5) 0.0087(5) 0.0141(5) C3 0.0227(7) 0.0199(7) 0.0133(6) 0.0039(5) 0.0074(5) 0.0122(5) O1A 0.0280(5) 0.0232(5) 0.0168(5) 0.0061(4) 0.0088(4) 0.0155(4) O1B 0.0364(6) 0.0290(6) 0.0148(5) 0.0083(4) 0.0119(4) 0.0210(5) C22 0.0198(7) 0.0180(6) 0.0197(7) -0.0001(5) 0.0034(5) 0.0078(5) C24 0.0268(7) 0.0216(7) 0.0238(7) 0.0066(5) 0.0055(6) 0.0132(6) C25 0.0256(7) 0.0206(7) 0.0196(7) 0.0049(5) 0.0061(5) 0.0102(6) C26 0.0325(8) 0.0266(8) 0.0221(7) 0.0054(6) 0.0027(6) 0.0124(6) N21 0.0218(6) 0.0186(6) 0.0201(6) 0.0022(4) 0.0057(4) 0.0115(5) N23 0.0249(6) 0.0196(6) 0.0208(6) 0.0027(5) 0.0080(5) 0.0120(5) C31 0.0163(6) 0.0160(6) 0.0150(6) 0.0007(5) 0.0034(5) 0.0077(5) C32 0.0188(6) 0.0171(6) 0.0130(6) 0.0031(5) 0.0047(5) 0.0102(5) C33 0.0196(6) 0.0173(6) 0.0126(6) 0.0025(5) 0.0043(5) 0.0107(5) O31A 0.0305(6) 0.0274(6) 0.0156(5) 0.0057(4) 0.0096(4) 0.0194(4) O31B 0.0234(5) 0.0194(5) 0.0187(5) 0.0038(4) 0.0047(4) 0.0137(4) O1W 0.0475(8) 0.0454(8) 0.0399(7) 0.0264(6) 0.0136(6) 0.0235(6) _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 O1A 1.2493(17) . ? C1 O1B 1.2799(16) . ? C1 C2 1.5160(18) . ? C2 C3 1.5221(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C3 1.528(2) 2_666 ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C22 N23 1.3292(18) . ? C22 N21 1.3338(18) . ? C22 C26 1.476(2) . ? C24 C25 1.349(2) . ? C24 N23 1.3775(19) . ? C24 H24 0.9500 . ? C25 N21 1.3826(18) . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? C31 O31B 1.2336(16) . ? C31 O31A 1.2992(16) . ? C31 C32 1.5138(17) . ? C32 C33 1.5151(17) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C33 1.530(2) 2_765 ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? O31A H31 0.8400 . ? O1W H1W 0.813(19) . ? O1W H2W 0.840(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 O1A C1 O1B 121.59(12) . . ? O1A C1 C2 120.88(11) . . ? O1B C1 C2 117.53(12) . . ? C1 C2 C3 115.18(11) . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2B 108.5 . . ? C3 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C3 111.67(13) . 2_666 ? C2 C3 H3A 109.3 . . ? C3 C3 H3A 109.3 2_666 . ? C2 C3 H3B 109.3 . . ? C3 C3 H3B 109.3 2_666 . ? H3A C3 H3B 107.9 . . ? N23 C22 N21 107.48(13) . . ? N23 C22 C26 125.92(13) . . ? N21 C22 C26 126.60(13) . . ? C25 C24 N23 107.13(13) . . ? C25 C24 H24 126.4 . . ? N23 C24 H24 126.4 . . ? C24 C25 N21 106.49(12) . . ? C24 C25 H25 126.8 . . ? N21 C25 H25 126.8 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 N21 C25 109.45(12) . . ? C22 N21 H21 125.3 . . ? C25 N21 H21 125.3 . . ? C22 N23 C24 109.45(12) . . ? C22 N23 H23 125.3 . . ? C24 N23 H23 125.3 . . ? O31B C31 O31A 121.51(12) . . ? O31B C31 C32 121.81(12) . . ? O31A C31 C32 116.67(11) . . ? C31 C32 C33 116.09(11) . . ? C31 C32 H32A 108.3 . . ? C33 C32 H32A 108.3 . . ? C31 C32 H32B 108.3 . . ? C33 C32 H32B 108.3 . . ? H32A C32 H32B 107.4 . . ? C32 C33 C33 110.75(13) . 2_765 ? C32 C33 H33A 109.5 . . ? C33 C33 H33A 109.5 2_765 . ? C32 C33 H33B 109.5 . . ? C33 C33 H33B 109.5 2_765 . ? H33A C33 H33B 108.1 . . ? C31 O31A H31 109.5 . . ? H1W O1W H2W 112(3) . . ? 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 O31A H31 O1B 0.84 1.63 2.4619(14) 173.9 . O1W H2W O1A 0.840(16) 2.008(17) 2.8358(16) 169(2) . N21 H21 O31B 0.88 1.86 2.7273(16) 166.9 2_675 N23 H23 O1A 0.88 1.88 2.7537(15) 173.3 2_765 O1W H1W O1W 0.813(19) 2.16(4) 2.724(3) 126(5) 2_756 _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 25.83 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.377 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.057 #============================================================================== data_6 _database_code_depnum_ccdc_archive 'CCDC 745375' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Succinic Acid and 2-Methylimidazole ; _chemical_name_common 'Succinic Acid and 2-Methylimidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 N2 O4' _chemical_formula_weight 200.20 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_H-M P21/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 8.1472(7) _cell_length_b 6.4965(5) _cell_length_c 9.0107(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.401(4) _cell_angle_gamma 90.00 _cell_volume 472.95(6) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1162 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9865 _exptl_absorpt_correction_T_max 0.9989 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6255 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1184 _reflns_number_gt 918 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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. Checkcif brings up an alert regarding short contacts between H26a..H26b and h26a..h26c, however this is an error by checkcif due to the methyl group being situated on a special position. The methyl group has been modelled using PART-1 with 0.5 occupancy. ; _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^)+(0.0325P)^2^+0.2656P] 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_extinction_coef ? _refine_ls_number_reflns 1184 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 C1 C 0.0771(3) 0.2500 0.6467(2) 0.0178(5) Uani 1 2 d S . . C2 C 0.2331(3) 0.2500 0.5710(2) 0.0204(5) Uani 1 2 d S . . H2A H 0.2314 0.1271 0.5059 0.024 Uiso 0.50 1 calc PR . . H2B H 0.2314 0.3729 0.5059 0.024 Uiso 0.50 1 calc PR . . C3 C 0.3935(3) 0.2500 0.6766(2) 0.0183(5) Uani 1 2 d S . . H3A H 0.3972 0.3732 0.7416 0.022 Uiso 0.50 1 calc PR . . H3B H 0.3972 0.1268 0.7416 0.022 Uiso 0.50 1 calc PR . . C4 C 0.5430(3) 0.2500 0.5934(2) 0.0173(5) Uani 1 2 d S . . O1A O -0.05845(19) 0.2500 0.55682(17) 0.0239(4) Uani 1 2 d S . . O1B O 0.0854(2) 0.2500 0.78505(17) 0.0228(4) Uani 1 2 d S . . O4A O 0.5365(2) 0.2500 0.45872(17) 0.0264(4) Uani 1 2 d S . . O4B O 0.68313(19) 0.2500 0.68621(17) 0.0234(4) Uani 1 2 d S . . H4 H 0.7637 0.2500 0.6367 0.050(10) Uiso 1 2 calc SR . . C22 C 1.0025(3) 0.2500 0.1452(2) 0.0206(5) Uani 1 2 d S . . C24 C 0.7421(3) 0.2500 0.0390(3) 0.0248(6) Uani 1 2 d S . . H24 H 0.6481 0.2500 -0.0353 0.030 Uiso 1 2 calc SR . . C25 C 0.7411(3) 0.2500 0.1877(3) 0.0237(5) Uani 1 2 d S . . H25 H 0.6462 0.2500 0.2389 0.028 Uiso 1 2 calc SR . . C26 C 1.1856(3) 0.2500 0.1634(3) 0.0280(6) Uani 1 2 d S . . H26A H 1.2238 0.2500 0.0647 0.042 Uiso 1 2 calc SR . . H26B H 1.2271 0.1268 0.2188 0.042 Uiso 0.50 1 calc PR . . H26C H 1.2271 0.3732 0.2188 0.042 Uiso 0.50 1 calc PR . . N21 N 0.9036(3) 0.2500 0.2520(2) 0.0233(5) Uani 1 2 d S . . H21 H 0.9371 0.2500 0.3489 0.048(9) Uiso 1 2 calc SR . . N23 N 0.9057(2) 0.2500 0.0146(2) 0.0221(5) Uani 1 2 d S . . H23 H 0.9406 0.2500 -0.0738 0.053(10) Uiso 1 2 calc SR . . 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 0.0141(12) 0.0210(12) 0.0183(11) 0.000 0.0026(9) 0.000 C2 0.0153(12) 0.0303(13) 0.0159(10) 0.000 0.0032(9) 0.000 C3 0.0138(11) 0.0262(12) 0.0153(10) 0.000 0.0037(8) 0.000 C4 0.0152(12) 0.0206(11) 0.0163(11) 0.000 0.0027(9) 0.000 O1A 0.0119(8) 0.0419(11) 0.0181(8) 0.000 0.0026(6) 0.000 O1B 0.0181(9) 0.0362(10) 0.0149(8) 0.000 0.0044(6) 0.000 O4A 0.0184(9) 0.0453(11) 0.0157(8) 0.000 0.0029(6) 0.000 O4B 0.0128(8) 0.0402(10) 0.0177(8) 0.000 0.0035(7) 0.000 C22 0.0260(13) 0.0185(11) 0.0180(11) 0.000 0.0054(9) 0.000 C24 0.0221(13) 0.0317(14) 0.0214(12) 0.000 0.0054(9) 0.000 C25 0.0236(13) 0.0264(13) 0.0223(12) 0.000 0.0070(9) 0.000 C26 0.0283(14) 0.0326(15) 0.0231(12) 0.000 0.0034(10) 0.000 N21 0.0299(12) 0.0259(11) 0.0145(10) 0.000 0.0048(8) 0.000 N23 0.0239(11) 0.0273(11) 0.0159(9) 0.000 0.0060(8) 0.000 _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 O1B 1.240(3) . ? C1 O1A 1.283(3) . ? C1 C2 1.518(3) . ? C2 C3 1.514(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.510(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O4A 1.208(3) . ? C4 O4B 1.326(3) . ? O4B H4 0.8400 . ? C22 N23 1.330(3) . ? C22 N21 1.333(3) . ? C22 C26 1.479(3) . ? C24 C25 1.341(3) . ? C24 N23 1.378(3) . ? C24 H24 0.9500 . ? C25 N21 1.375(3) . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? 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 O1B C1 O1A 124.5(2) . . ? O1B C1 C2 120.75(19) . . ? O1A C1 C2 114.78(19) . . ? C3 C2 C1 115.01(18) . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2B 108.5 . . ? C1 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? C4 C3 C2 111.97(18) . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? O4A C4 O4B 123.8(2) . . ? O4A C4 C3 124.4(2) . . ? O4B C4 C3 111.76(18) . . ? C4 O4B H4 109.5 . . ? N23 C22 N21 107.1(2) . . ? N23 C22 C26 125.0(2) . . ? N21 C22 C26 127.9(2) . . ? C25 C24 N23 106.9(2) . . ? C25 C24 H24 126.6 . . ? N23 C24 H24 126.6 . . ? C24 C25 N21 107.0(2) . . ? C24 C25 H25 126.5 . . ? N21 C25 H25 126.5 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 N21 C25 109.53(19) . . ? C22 N21 H21 125.2 . . ? C25 N21 H21 125.2 . . ? C22 N23 C24 109.52(19) . . ? C22 N23 H23 125.2 . . ? C24 N23 H23 125.2 . . ? 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 O4B H4 O1A 0.84 1.70 2.535(2) 173.0 1_655 N21 H21 O1A 0.88 1.87 2.724(2) 163.2 1_655 N23 H23 O1B 0.88 1.84 2.684(2) 159.3 1_654 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.284 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.052 #============================================================================== data_7 _database_code_depnum_ccdc_archive 'CCDC 745376' _audit_creation_method SHELXL-97 _chemical_name_systematic ; fumaric acid & 2-methylimidazole ; _chemical_name_common 'fumaric acid & 2-methylimidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 N2 O4' _chemical_formula_weight 198.18 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_H-M P21/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 8.0829(5) _cell_length_b 6.2852(4) _cell_length_c 9.0979(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.551(4) _cell_angle_gamma 90.00 _cell_volume 458.19(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1544 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9873 _exptl_absorpt_correction_T_max 0.9988 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4633 _diffrn_reflns_av_R_equivalents 0.0813 _diffrn_reflns_av_sigmaI/netI 0.0716 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1138 _reflns_number_gt 802 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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. Checkcif brings up alerts due to the manner in which the hydrogen atoms in the methyl group are modelled - HFIX 33 was used as this best fitted the data. ; _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^)+(0.0461P)^2^+0.5865P] 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_extinction_coef ? _refine_ls_number_reflns 1138 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1049 _refine_ls_R_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.1575 _refine_ls_wR_factor_gt 0.1392 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 C1 C 0.4928(4) 0.2500 0.4169(4) 0.0212(8) Uani 1 2 d S . . C2 C 0.6461(4) 0.2500 0.3430(4) 0.0232(8) Uani 1 2 d S . . H2 H 0.6361 0.2500 0.2378 0.028 Uiso 1 2 calc SR . . C3 C 0.7936(5) 0.2500 0.4197(4) 0.0260(9) Uani 1 2 d S . . H3 H 0.7999 0.2500 0.5247 0.031 Uiso 1 2 calc SR . . C4 C 0.9551(4) 0.2500 0.3543(4) 0.0200(8) Uani 1 2 d S . . O1A O 0.4963(3) 0.2500 0.5505(3) 0.0266(6) Uani 1 2 d S . . O1B O 0.3547(3) 0.2500 0.3220(3) 0.0253(6) Uani 1 2 d S . . H1 H 0.2717 0.2500 0.3687 0.059(16) Uiso 1 2 calc SR . . O4A O 1.0876(3) 0.2500 0.4461(3) 0.0288(7) Uani 1 2 d S . . O4B O 0.9498(3) 0.2500 0.2166(3) 0.0269(6) Uani 1 2 d S . . C22 C 0.0338(5) 0.2500 0.8564(4) 0.0245(8) Uani 1 2 d S . . C24 C 0.2944(5) 0.2500 0.9677(4) 0.0322(10) Uani 1 2 d S . . H24 H 0.3874 0.2500 1.0433 0.039 Uiso 1 2 calc SR . . C25 C 0.2997(5) 0.2500 0.8212(4) 0.0306(9) Uani 1 2 d S . . H25 H 0.3971 0.2500 0.7732 0.037 Uiso 1 2 calc SR . . C26 C -0.1501(5) 0.2500 0.8327(4) 0.0314(9) Uani 1 2 d S . . H26A H -0.1924 0.2500 0.9288 0.047 Uiso 1 2 calc SR . . H26B H -0.1900 0.1227 0.7768 0.047 Uiso 0.50 1 calc PR . . H26C H -0.1900 0.3773 0.7768 0.047 Uiso 0.50 1 calc PR . . N21 N 0.1383(4) 0.2500 0.7540(3) 0.0263(7) Uani 1 2 d S . . H21 H 0.1077 0.2500 0.6575 0.036(12) Uiso 1 2 calc SR . . N23 N 0.1275(4) 0.2500 0.9879(3) 0.0275(8) Uani 1 2 d S . . H23 H 0.0894 0.2500 1.0742 0.053(15) Uiso 1 2 calc SR . . 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 0.0176(18) 0.025(2) 0.0217(18) 0.000 0.0053(15) 0.000 C2 0.0187(19) 0.032(2) 0.0199(18) 0.000 0.0065(15) 0.000 C3 0.0220(19) 0.039(2) 0.0189(17) 0.000 0.0096(15) 0.000 C4 0.0173(17) 0.026(2) 0.0173(16) 0.000 0.0041(14) 0.000 O1A 0.0226(14) 0.0408(17) 0.0177(12) 0.000 0.0079(10) 0.000 O1B 0.0130(13) 0.0437(17) 0.0200(13) 0.000 0.0057(11) 0.000 O4A 0.0162(13) 0.0530(18) 0.0175(12) 0.000 0.0032(10) 0.000 O4B 0.0228(13) 0.0417(16) 0.0171(12) 0.000 0.0057(10) 0.000 C22 0.034(2) 0.022(2) 0.0189(17) 0.000 0.0071(15) 0.000 C24 0.027(2) 0.047(3) 0.0244(19) 0.000 0.0080(16) 0.000 C25 0.028(2) 0.037(2) 0.028(2) 0.000 0.0100(17) 0.000 C26 0.034(2) 0.037(2) 0.0246(19) 0.000 0.0095(17) 0.000 N21 0.0339(18) 0.0292(18) 0.0171(15) 0.000 0.0081(13) 0.000 N23 0.0300(18) 0.036(2) 0.0177(15) 0.000 0.0074(14) 0.000 _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 O1A 1.212(4) . ? C1 O1B 1.318(4) . ? C1 C2 1.485(5) . ? C2 C3 1.300(5) . ? C2 H2 0.9500 . ? C3 C4 1.504(5) . ? C3 H3 0.9500 . ? C4 O4B 1.248(4) . ? C4 O4A 1.269(4) . ? O1B H1 0.8400 . ? C22 N23 1.329(5) . ? C22 N21 1.338(5) . ? C22 C26 1.473(5) . ? C24 C25 1.339(5) . ? C24 N23 1.386(5) . ? C24 H24 0.9500 . ? C25 N21 1.366(5) . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? 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 O1A C1 O1B 124.3(3) . . ? O1A C1 C2 122.9(3) . . ? O1B C1 C2 112.9(3) . . ? C3 C2 C1 121.2(3) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 124.7(3) . . ? C2 C3 H3 117.6 . . ? C4 C3 H3 117.6 . . ? O4B C4 O4A 125.1(3) . . ? O4B C4 C3 118.7(3) . . ? O4A C4 C3 116.1(3) . . ? C1 O1B H1 109.5 . . ? N23 C22 N21 106.8(3) . . ? N23 C22 C26 125.2(3) . . ? N21 C22 C26 128.0(3) . . ? C25 C24 N23 106.9(3) . . ? C25 C24 H24 126.6 . . ? N23 C24 H24 126.6 . . ? C24 C25 N21 107.0(3) . . ? C24 C25 H25 126.5 . . ? N21 C25 H25 126.5 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 N21 C25 110.0(3) . . ? C22 N21 H21 125.0 . . ? C25 N21 H21 125.0 . . ? C22 N23 C24 109.3(3) . . ? C22 N23 H23 125.3 . . ? C24 N23 H23 125.3 . . ? 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 O1B H1 O4A 0.84 1.73 2.564(3) 173.8 1_455 N21 H21 O4A 0.88 1.91 2.777(4) 168.6 1_455 N23 H23 O4B 0.88 1.83 2.679(4) 162.5 1_456 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.419 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.064 #============================================================================== data_8 _database_code_depnum_ccdc_archive 'CCDC 745377' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Suberic acid & 2-methylimidazole ; _chemical_name_common 'Suberic acid & 2-methylimidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 N2 O4' _chemical_formula_weight 256.30 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 7.3683(4) _cell_length_b 9.0497(3) _cell_length_c 10.7486(5) _cell_angle_alpha 76.546(3) _cell_angle_beta 80.396(2) _cell_angle_gamma 76.933(3) _cell_volume 674.05(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2981 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 27.48 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9915 _exptl_absorpt_correction_T_max 0.9981 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14400 _diffrn_reflns_av_R_equivalents 0.0754 _diffrn_reflns_av_sigmaI/netI 0.0659 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3090 _reflns_number_gt 1951 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^)+(0.0343P)^2^+0.2653P] 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 SHELXL _refine_ls_extinction_coef 0.055(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3090 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1074 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1281 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.043 _refine_ls_shift/su_mean 0.005 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 C8 C 0.426(3) 0.828(3) 0.682(3) 0.059(6) Uani 0.41(6) 1 d P A 1 O8A O 0.344(5) 0.735(3) 0.785(3) 0.047(4) Uani 0.41(6) 1 d P A 1 H8 H 0.3120 0.7813 0.8467 0.071 Uiso 0.41(6) 1 calc PR A 1 O8B O 0.391(6) 0.9631(14) 0.6903(12) 0.059(5) Uani 0.41(6) 1 d P A 1 C9 C 0.4268(17) 0.8185(14) 0.7011(15) 0.029(3) Uani 0.59(6) 1 d P A 2 O9A O 0.371(4) 0.7290(19) 0.803(2) 0.053(4) Uani 0.59(6) 1 d P A 2 H9 H 0.3356 0.7787 0.8629 0.080 Uiso 0.59(6) 1 calc PR A 2 O9B O 0.473(4) 0.940(2) 0.7005(16) 0.069(3) Uani 0.59(6) 1 d P A 2 C1 C 0.1789(3) 0.7601(2) 0.09026(18) 0.0361(5) Uani 1 1 d . . . C2 C 0.1123(3) 0.8189(2) 0.21369(18) 0.0382(5) Uani 1 1 d . . . H2A H -0.0028 0.8993 0.2013 0.046 Uiso 1 1 calc R . . H2B H 0.2094 0.8689 0.2309 0.046 Uiso 1 1 calc R . . C3 C 0.0705(3) 0.6955(2) 0.33110(18) 0.0422(5) Uani 1 1 d . . . H3B H 0.1829 0.6117 0.3407 0.051 Uiso 1 1 calc R . . H3A H -0.0326 0.6501 0.3166 0.051 Uiso 1 1 calc R . . C4 C 0.0151(3) 0.7559(2) 0.45605(19) 0.0470(5) Uani 1 1 d . . . H4A H -0.0235 0.6717 0.5254 0.056 Uiso 1 1 calc R . . H4B H -0.0956 0.8413 0.4452 0.056 Uiso 1 1 calc R . . C5 C 0.1680(3) 0.8149(2) 0.49948(18) 0.0418(5) Uani 1 1 d . . . H5A H 0.2099 0.8968 0.4293 0.050 Uiso 1 1 calc R . . H5B H 0.1136 0.8625 0.5749 0.050 Uiso 1 1 calc R . . C6 C 0.3373(3) 0.6906(2) 0.5352(2) 0.0449(5) Uani 1 1 d . A . H6A H 0.3915 0.6425 0.4599 0.054 Uiso 1 1 calc R . . H6B H 0.2956 0.6090 0.6058 0.054 Uiso 1 1 calc R . . C7 C 0.4897(3) 0.7502(2) 0.5776(2) 0.0465(5) Uani 1 1 d . . . H7B H 0.5923 0.6617 0.6027 0.056 Uiso 1 1 calc R A 1 H7A H 0.5423 0.8223 0.5034 0.056 Uiso 1 1 calc R A 1 O1A O 0.1811(2) 0.62346(15) 0.08931(14) 0.0562(5) Uani 1 1 d . . . O1B O 0.2296(2) 0.85766(15) -0.00895(12) 0.0464(4) Uani 1 1 d . . . C22 C 0.2291(3) 1.2629(2) 0.03459(19) 0.0396(5) Uani 1 1 d . . . C24 C 0.3745(3) 1.3620(2) -0.1512(2) 0.0470(5) Uani 1 1 d . . . H24 H 0.4288 1.4332 -0.2185 0.056 Uiso 1 1 calc R . . C25 C 0.3677(3) 1.2160(2) -0.1534(2) 0.0458(5) Uani 1 1 d . . . H25 H 0.4165 1.1640 -0.2227 0.055 Uiso 1 1 calc R . . C26 C 0.1276(4) 1.2484(3) 0.1656(2) 0.0605(7) Uani 1 1 d . . . H26A H 0.1029 1.3484 0.1921 0.091 Uiso 1 1 calc R . . H26B H 0.2039 1.1701 0.2254 0.091 Uiso 1 1 calc R . . H26C H 0.0083 1.2172 0.1665 0.091 Uiso 1 1 calc R . . N21 N 0.2777(2) 1.15581(19) -0.03736(16) 0.0421(4) Uani 1 1 d . . . N23 N 0.2884(2) 1.38890(18) -0.03384(16) 0.0411(4) Uani 1 1 d . . . H21 H 0.257(3) 1.056(3) -0.015(2) 0.056(6) Uiso 1 1 d . . . H23 H 0.265(3) 1.479(3) -0.005(2) 0.067(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 C8 0.064(9) 0.070(11) 0.044(8) 0.020(7) -0.028(7) -0.033(8) O8A 0.071(7) 0.058(7) 0.023(5) -0.017(4) 0.001(6) -0.030(5) O8B 0.110(13) 0.025(4) 0.042(3) -0.006(2) -0.007(5) -0.018(5) C9 0.042(5) 0.024(4) 0.024(4) -0.013(4) -0.003(3) -0.005(3) O9A 0.091(8) 0.036(3) 0.037(6) -0.011(3) -0.003(5) -0.021(3) O9B 0.094(8) 0.056(4) 0.067(4) -0.025(3) 0.010(4) -0.036(5) C1 0.0457(12) 0.0315(10) 0.0352(11) -0.0091(8) -0.0074(9) -0.0114(8) C2 0.0497(12) 0.0337(10) 0.0349(11) -0.0120(8) -0.0046(9) -0.0107(9) C3 0.0527(13) 0.0411(11) 0.0368(11) -0.0069(9) -0.0075(10) -0.0166(9) C4 0.0512(13) 0.0536(12) 0.0356(11) -0.0071(9) -0.0010(10) -0.0141(10) C5 0.0552(13) 0.0391(11) 0.0315(11) -0.0121(8) -0.0045(9) -0.0052(9) C6 0.0597(14) 0.0402(11) 0.0373(11) -0.0161(9) -0.0085(10) -0.0042(10) C7 0.0485(13) 0.0508(12) 0.0401(12) -0.0166(10) 0.0003(10) -0.0064(10) O1A 0.0926(12) 0.0344(8) 0.0477(9) -0.0176(6) 0.0054(8) -0.0252(8) O1B 0.0769(11) 0.0346(7) 0.0307(8) -0.0078(6) -0.0014(7) -0.0195(7) C22 0.0449(12) 0.0336(10) 0.0439(12) -0.0093(8) -0.0120(10) -0.0086(9) C24 0.0607(14) 0.0389(11) 0.0432(12) -0.0100(9) -0.0028(11) -0.0143(10) C25 0.0575(14) 0.0392(11) 0.0450(13) -0.0167(9) -0.0044(11) -0.0108(10) C26 0.0766(18) 0.0562(14) 0.0519(15) -0.0133(11) -0.0003(13) -0.0224(13) N21 0.0545(11) 0.0274(9) 0.0491(11) -0.0103(7) -0.0118(9) -0.0108(8) N23 0.0566(11) 0.0279(9) 0.0440(10) -0.0118(7) -0.0117(8) -0.0100(8) _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 C8 O8B 1.21(2) . ? C8 O8A 1.36(4) . ? C8 C7 1.42(2) . ? O8A H8 0.8400 . ? C9 O9B 1.220(15) . ? C9 O9A 1.27(3) . ? C9 C7 1.551(11) . ? O9A H9 0.8400 . ? C1 O1A 1.235(2) . ? C1 O1B 1.278(2) . ? C1 C2 1.509(3) . ? C2 C3 1.518(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.525(3) . ? C3 H3B 0.9900 . ? C3 H3A 0.9900 . ? C4 C5 1.529(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.514(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.523(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7B 0.9900 . ? C7 H7A 0.9900 . ? C22 N23 1.327(2) . ? C22 N21 1.329(2) . ? C22 C26 1.472(3) . ? C24 C25 1.340(3) . ? C24 N23 1.363(3) . ? C24 H24 0.9500 . ? C25 N21 1.365(3) . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N21 H21 0.92(2) . ? N23 H23 0.91(2) . ? 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 O8B C8 O8A 113(3) . . ? O8B C8 C7 134(3) . . ? O8A C8 C7 110.8(19) . . ? O9B C9 O9A 123.4(14) . . ? O9B C9 C7 117.0(12) . . ? O9A C9 C7 117.4(11) . . ? C9 O9A H9 109.5 . . ? O1A C1 O1B 123.65(18) . . ? O1A C1 C2 119.52(17) . . ? O1B C1 C2 116.83(15) . . ? C1 C2 C3 114.74(15) . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? C3 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C2 C3 C4 113.73(16) . . ? C2 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? H3B C3 H3A 107.7 . . ? C3 C4 C5 115.27(17) . . ? C3 C4 H4A 108.5 . . ? C5 C4 H4A 108.5 . . ? C3 C4 H4B 108.5 . . ? C5 C4 H4B 108.5 . . ? H4A C4 H4B 107.5 . . ? C6 C5 C4 114.03(16) . . ? C6 C5 H5A 108.7 . . ? C4 C5 H5A 108.7 . . ? C6 C5 H5B 108.7 . . ? C4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C5 C6 C7 113.79(16) . . ? C5 C6 H6A 108.8 . . ? C7 C6 H6A 108.8 . . ? C5 C6 H6B 108.8 . . ? C7 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C8 C7 C6 114.0(10) . . ? C8 C7 C9 5.9(16) . . ? C6 C7 C9 114.1(5) . . ? C8 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? C9 C7 H7B 103.6 . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7A 108.8 . . ? C9 C7 H7A 113.6 . . ? H7B C7 H7A 107.6 . . ? N23 C22 N21 107.26(18) . . ? N23 C22 C26 125.26(18) . . ? N21 C22 C26 127.48(18) . . ? C25 C24 N23 106.90(19) . . ? C25 C24 H24 126.5 . . ? N23 C24 H24 126.5 . . ? C24 C25 N21 107.12(19) . . ? C24 C25 H25 126.4 . . ? N21 C25 H25 126.4 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 N21 C25 109.20(16) . . ? C22 N21 H21 127.1(14) . . ? C25 N21 H21 123.7(14) . . ? C22 N23 C24 109.51(16) . . ? C22 N23 H23 122.4(15) . . ? C24 N23 H23 127.9(15) . . ? 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 N21 H21 O1B 0.92(2) 1.84(2) 2.741(2) 167(2) . O9A H9 O1B 0.84 1.69 2.52(2) 168.6 1_556 O8A H8 O1B 0.84 1.80 2.64(3) 172.1 1_556 N23 H23 O1A 0.91(2) 1.78(3) 2.661(2) 163(2) 1_565 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.169 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.038 #============================================================================== data_9 _database_code_depnum_ccdc_archive 'CCDC 745378' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Fumaric acid and 1,2-dimethylimidazole ; _chemical_name_common 'Fumaric acid and 1,2-dimethylimidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H12 N2 O4' _chemical_formula_weight 212.21 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_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.6480(7) _cell_length_b 11.6730(9) _cell_length_c 11.2040(11) _cell_angle_alpha 90.00 _cell_angle_beta 93.547(4) _cell_angle_gamma 90.00 _cell_volume 998.32(15) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4271 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9911 _exptl_absorpt_correction_T_max 0.9989 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12957 _diffrn_reflns_av_R_equivalents 0.1086 _diffrn_reflns_av_sigmaI/netI 0.0652 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1745 _reflns_number_gt 1177 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0000P)^2^+3.2220P] 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_extinction_coef ? _refine_ls_number_reflns 1745 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1343 _refine_ls_R_factor_gt 0.0845 _refine_ls_wR_factor_ref 0.1631 _refine_ls_wR_factor_gt 0.1424 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.003 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 0.0820(6) 0.0451(3) -0.6563(4) 0.0239(10) Uani 1 1 d . . . C2 C 0.1224(6) 0.1612(4) -0.6053(4) 0.0249(10) Uani 1 1 d . . . H2 H 0.0671 0.2264 -0.6417 0.030 Uiso 1 1 calc R . . C3 C 0.2325(6) 0.1757(4) -0.5112(4) 0.0257(11) Uani 1 1 d . . . H3 H 0.2875 0.1098 -0.4761 0.031 Uiso 1 1 calc R . . C4 C 0.2755(5) 0.2888(4) -0.4572(4) 0.0232(10) Uani 1 1 d . . . O1A O 0.1598(4) -0.0406(2) -0.6098(2) 0.0256(7) Uani 1 1 d . . . O1B O -0.0275(4) 0.0391(2) -0.7462(3) 0.0288(8) Uani 1 1 d . . . O4A O 0.3851(4) 0.2796(2) -0.3607(3) 0.0290(8) Uani 1 1 d . . . H4 H 0.4096 0.3452 -0.3337 0.07(2) Uiso 1 1 calc R . . O4B O 0.2159(4) 0.3797(2) -0.4950(3) 0.0319(8) Uani 1 1 d . . . C22 C 0.4286(6) 0.1714(4) -0.8043(4) 0.0236(10) Uani 1 1 d . . . C24 C 0.5687(6) 0.2749(4) -0.6652(4) 0.0247(10) Uani 1 1 d . . . H24 H 0.6103 0.3391 -0.6197 0.030 Uiso 1 1 calc R . . C25 C 0.6084(6) 0.1651(4) -0.6425(4) 0.0248(10) Uani 1 1 d . . . H25 H 0.6820 0.1367 -0.5778 0.030 Uiso 1 1 calc R . . C26 C 0.5309(6) -0.0242(3) -0.7458(4) 0.0264(11) Uani 1 1 d . . . H26A H 0.4722 -0.0462 -0.8226 0.040 Uiso 1 1 calc R . . H26B H 0.4729 -0.0615 -0.6806 0.040 Uiso 1 1 calc R . . H26C H 0.6539 -0.0481 -0.7437 0.040 Uiso 1 1 calc R . . C27 C 0.3165(6) 0.1413(4) -0.9118(4) 0.0279(11) Uani 1 1 d . . . H27A H 0.3904 0.1189 -0.9763 0.042 Uiso 1 1 calc R . . H27B H 0.2452 0.2077 -0.9372 0.042 Uiso 1 1 calc R . . H27C H 0.2397 0.0774 -0.8932 0.042 Uiso 1 1 calc R . . N21 N 0.5215(5) 0.1011(3) -0.7315(3) 0.0253(9) Uani 1 1 d . . . N23 N 0.4573(4) 0.2785(3) -0.7657(3) 0.0239(9) Uani 1 1 d . . . H23 H 0.4123 0.3408 -0.7993 0.028(13) 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) 0.018(2) 0.031(3) -0.001(2) 0.003(2) -0.0014(19) C2 0.033(3) 0.020(2) 0.022(2) 0.0034(18) -0.001(2) 0.0026(19) C3 0.028(3) 0.021(2) 0.028(3) 0.0048(19) 0.000(2) -0.0006(19) C4 0.019(2) 0.026(2) 0.025(2) -0.002(2) 0.0042(19) -0.0047(19) O1A 0.0298(17) 0.0179(15) 0.0281(17) 0.0014(14) -0.0065(14) 0.0023(14) O1B 0.0347(18) 0.0204(16) 0.0296(18) -0.0007(13) -0.0103(15) -0.0018(14) O4A 0.0332(19) 0.0209(17) 0.0312(18) -0.0059(15) -0.0101(15) 0.0001(15) O4B 0.0379(19) 0.0219(17) 0.0350(19) 0.0033(14) -0.0054(15) 0.0008(15) C22 0.025(2) 0.022(2) 0.025(3) -0.0005(19) 0.0041(19) 0.0030(19) C24 0.029(3) 0.025(2) 0.019(2) -0.0009(19) -0.004(2) -0.0037(19) C25 0.025(2) 0.028(2) 0.021(2) 0.000(2) -0.0042(19) 0.004(2) C26 0.032(3) 0.019(2) 0.026(2) 0.0003(19) -0.006(2) 0.0019(19) C27 0.031(3) 0.025(2) 0.027(3) 0.0038(19) -0.005(2) 0.006(2) N21 0.030(2) 0.0183(18) 0.027(2) 0.0015(16) -0.0013(17) 0.0023(16) N23 0.023(2) 0.022(2) 0.026(2) 0.0039(17) -0.0022(17) 0.0001(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1A 1.261(5) . ? C1 O1B 1.271(5) . ? C1 C2 1.496(6) . ? C2 C3 1.319(6) . ? C2 H2 0.9500 . ? C3 C4 1.481(6) . ? C3 H3 0.9500 . ? C4 O4B 1.220(5) . ? C4 O4A 1.331(5) . ? O4A H4 0.8400 . ? C22 N21 1.331(5) . ? C22 N23 1.336(5) . ? C22 C27 1.477(6) . ? C24 C25 1.338(6) . ? C24 N23 1.370(5) . ? C24 H24 0.9500 . ? C25 N21 1.383(5) . ? C25 H25 0.9500 . ? C26 N21 1.473(5) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? N23 H23 0.8800 . ? 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 O1A C1 O1B 123.7(4) . . ? O1A C1 C2 118.7(4) . . ? O1B C1 C2 117.6(4) . . ? C3 C2 C1 121.9(4) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C2 C3 C4 123.7(4) . . ? C2 C3 H3 118.1 . . ? C4 C3 H3 118.1 . . ? O4B C4 O4A 123.7(4) . . ? O4B C4 C3 124.4(4) . . ? O4A C4 C3 111.8(4) . . ? C4 O4A H4 109.5 . . ? N21 C22 N23 107.9(4) . . ? N21 C22 C27 127.9(4) . . ? N23 C22 C27 124.2(4) . . ? C25 C24 N23 107.9(4) . . ? C25 C24 H24 126.0 . . ? N23 C24 H24 126.0 . . ? C24 C25 N21 106.7(4) . . ? C24 C25 H25 126.7 . . ? N21 C25 H25 126.7 . . ? N21 C26 H26A 109.5 . . ? N21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C22 N21 C25 108.8(3) . . ? C22 N21 C26 125.0(4) . . ? C25 N21 C26 126.2(4) . . ? C22 N23 C24 108.6(4) . . ? C22 N23 H23 125.7 . . ? C24 N23 H23 125.7 . . ? 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 O4A H4 O1B 0.84 1.72 2.543(4) 165.7 4_666 N23 H23 O1A 0.88 1.78 2.656(4) 169.8 2_553 N23 H23 O1B 0.88 2.52 3.090(4) 123.4 2_553 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.268 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.071 #============================================================================== # Attachment '10-19_rev.cif' data_10 _database_code_depnum_ccdc_archive 'CCDC 745379' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Suberic acid & 4-methylimidazole ; _chemical_name_common 'Suberic acid & 4-methylimidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 N2 O4' _chemical_formula_weight 256.30 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_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.8691(7) _cell_length_b 13.2988(17) _cell_length_c 12.1250(14) _cell_angle_alpha 90.00 _cell_angle_beta 109.500(7) _cell_angle_gamma 90.00 _cell_volume 1348.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3149 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description shard _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9906 _exptl_absorpt_correction_T_max 0.9991 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15792 _diffrn_reflns_av_R_equivalents 0.1489 _diffrn_reflns_av_sigmaI/netI 0.1170 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2374 _reflns_number_gt 1547 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0000P)^2^+1.8819P] 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_extinction_coef ? _refine_ls_number_reflns 2374 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1540 _refine_ls_R_factor_gt 0.0933 _refine_ls_wR_factor_ref 0.1316 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _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 C1 C -0.0643(4) 0.0988(3) -0.2303(3) 0.0203(9) Uani 1 1 d . . . C2 C 0.0622(4) 0.1297(3) -0.1182(3) 0.0249(9) Uani 1 1 d . . . H2A H 0.0095 0.1597 -0.0657 0.030 Uiso 1 1 calc R . . H2B H 0.1300 0.1822 -0.1357 0.030 Uiso 1 1 calc R . . C3 C 0.1684(4) 0.0438(3) -0.0544(3) 0.0241(9) Uani 1 1 d . . . H3B H 0.2200 0.0130 -0.1071 0.029 Uiso 1 1 calc R . . H3A H 0.1012 -0.0083 -0.0354 0.029 Uiso 1 1 calc R . . C4 C 0.2976(4) 0.0769(3) 0.0580(3) 0.0253(9) Uani 1 1 d . . . H4A H 0.3660 0.1281 0.0387 0.030 Uiso 1 1 calc R . . H4B H 0.2461 0.1088 0.1100 0.030 Uiso 1 1 calc R . . C5 C 0.4024(4) -0.0095(3) 0.1231(3) 0.0234(9) Uani 1 1 d . . . H5B H 0.4398 -0.0480 0.0672 0.028 Uiso 1 1 calc R . . H5A H 0.3368 -0.0553 0.1528 0.028 Uiso 1 1 calc R . . C6 C 0.5481(4) 0.0238(3) 0.2256(3) 0.0225(9) Uani 1 1 d . . . H6B H 0.6159 -0.0357 0.2572 0.027 Uiso 1 1 calc R . . H6A H 0.6118 0.0714 0.1964 0.027 Uiso 1 1 calc R . . C7 C 0.5060(4) 0.0740(3) 0.3248(3) 0.0207(9) Uani 1 1 d . . . H7B H 0.4383 0.1335 0.2933 0.025 Uiso 1 1 calc R . . H7A H 0.4421 0.0264 0.3539 0.025 Uiso 1 1 calc R . . C8 C 0.6502(4) 0.1070(3) 0.4269(3) 0.0202(9) Uani 1 1 d . . . O1A O -0.1419(3) 0.17683(18) -0.2917(2) 0.0268(7) Uani 1 1 d . . . H1 H -0.2113 0.1563 -0.3534 0.058(15) Uiso 1 1 calc R . . O1B O -0.0940(3) 0.0128(2) -0.2607(2) 0.0327(7) Uani 1 1 d . . . O8A O 0.6254(3) 0.12814(19) 0.5220(2) 0.0231(6) Uani 1 1 d . . . O8B O 0.7824(3) 0.1125(2) 0.4133(2) 0.0303(7) Uani 1 1 d . . . C22 C 1.1963(4) 0.1208(3) 0.4825(3) 0.0212(9) Uani 1 1 d . . . H22 H 1.1760 0.0751 0.4190 0.025 Uiso 1 1 calc R . . C24 C 1.3193(4) 0.2234(3) 0.6275(3) 0.0210(9) Uani 1 1 d . . . C25 C 1.1637(4) 0.2198(3) 0.6170(3) 0.0225(9) Uani 1 1 d . . . H25 H 1.1144 0.2553 0.6638 0.027 Uiso 1 1 calc R . . C26 C 1.4565(4) 0.2785(3) 0.7120(3) 0.0299(10) Uani 1 1 d . . . H26A H 1.4178 0.3192 0.7643 0.045 Uiso 1 1 calc R . . H26B H 1.5060 0.3223 0.6688 0.045 Uiso 1 1 calc R . . H26C H 1.5357 0.2300 0.7582 0.045 Uiso 1 1 calc R . . N21 N 1.0887(4) 0.1556(2) 0.5261(2) 0.0240(8) Uani 1 1 d . . . H21 H 0.9863 0.1404 0.5013 0.054(14) Uiso 1 1 calc R . . N23 N 1.3380(4) 0.1604(2) 0.5422(2) 0.0213(7) Uani 1 1 d . . . H23 H 1.4284 0.1485 0.5295 0.061(15) 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 0.018(2) 0.025(2) 0.019(2) 0.0003(19) 0.0061(16) 0.0023(17) C2 0.027(2) 0.025(2) 0.020(2) -0.0046(18) 0.0033(17) -0.0033(18) C3 0.025(2) 0.028(2) 0.017(2) -0.0015(18) 0.0052(16) 0.0012(17) C4 0.025(2) 0.026(2) 0.020(2) -0.0020(18) 0.0015(17) -0.0020(18) C5 0.024(2) 0.026(2) 0.020(2) 0.0019(18) 0.0073(17) 0.0011(17) C6 0.022(2) 0.027(2) 0.017(2) 0.0042(18) 0.0055(16) 0.0026(17) C7 0.016(2) 0.023(2) 0.021(2) 0.0020(17) 0.0028(15) 0.0012(16) C8 0.020(2) 0.021(2) 0.020(2) 0.0018(18) 0.0059(17) -0.0022(17) O1A 0.0232(15) 0.0241(16) 0.0243(16) -0.0019(13) -0.0038(12) -0.0003(12) O1B 0.0348(17) 0.0226(17) 0.0293(16) -0.0061(13) -0.0042(12) 0.0006(13) O8A 0.0179(14) 0.0340(17) 0.0159(14) -0.0009(12) 0.0038(11) 0.0001(11) O8B 0.0166(15) 0.0485(19) 0.0256(15) -0.0068(13) 0.0069(12) -0.0077(13) C22 0.023(2) 0.022(2) 0.0149(19) -0.0024(17) 0.0004(17) 0.0000(17) C24 0.020(2) 0.025(2) 0.016(2) 0.0007(18) 0.0026(16) 0.0000(17) C25 0.024(2) 0.025(2) 0.020(2) -0.0040(18) 0.0089(17) -0.0008(18) C26 0.026(2) 0.033(3) 0.027(2) -0.007(2) 0.0040(18) -0.0014(18) N21 0.0163(19) 0.032(2) 0.0230(18) -0.0005(16) 0.0050(14) 0.0013(14) N23 0.0171(18) 0.0272(19) 0.0201(17) -0.0011(15) 0.0067(14) 0.0002(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1B 1.204(4) . ? C1 O1A 1.327(4) . ? C1 C2 1.502(5) . ? C2 C3 1.518(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.524(4) . ? C3 H3B 0.9900 . ? C3 H3A 0.9900 . ? C4 C5 1.523(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.529(5) . ? C5 H5B 0.9900 . ? C5 H5A 0.9900 . ? C6 C7 1.527(5) . ? C6 H6B 0.9900 . ? C6 H6A 0.9900 . ? C7 C8 1.518(5) . ? C7 H7B 0.9900 . ? C7 H7A 0.9900 . ? C8 O8B 1.239(4) . ? C8 O8A 1.275(4) . ? O1A H1 0.8400 . ? C22 N21 1.320(4) . ? C22 N23 1.332(4) . ? C22 H22 0.9500 . ? C24 C25 1.343(5) . ? C24 N23 1.383(4) . ? C24 C26 1.495(5) . ? C25 N21 1.377(4) . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? 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 O1B C1 O1A 123.5(3) . . ? O1B C1 C2 123.9(3) . . ? O1A C1 C2 112.6(3) . . ? C1 C2 C3 113.9(3) . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2B 108.8 . . ? C3 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C2 C3 C4 113.1(3) . . ? C2 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? H3B C3 H3A 107.8 . . ? C5 C4 C3 113.1(3) . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4B 109.0 . . ? C3 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C4 C5 C6 114.0(3) . . ? C4 C5 H5B 108.8 . . ? C6 C5 H5B 108.8 . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5A 108.8 . . ? H5B C5 H5A 107.6 . . ? C7 C6 C5 113.9(3) . . ? C7 C6 H6B 108.8 . . ? C5 C6 H6B 108.8 . . ? C7 C6 H6A 108.8 . . ? C5 C6 H6A 108.8 . . ? H6B C6 H6A 107.7 . . ? C8 C7 C6 114.1(3) . . ? C8 C7 H7B 108.7 . . ? C6 C7 H7B 108.7 . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7A 108.7 . . ? H7B C7 H7A 107.6 . . ? O8B C8 O8A 124.3(3) . . ? O8B C8 C7 119.1(3) . . ? O8A C8 C7 116.6(3) . . ? C1 O1A H1 109.5 . . ? N21 C22 N23 108.7(3) . . ? N21 C22 H22 125.7 . . ? N23 C22 H22 125.7 . . ? C25 C24 N23 106.5(3) . . ? C25 C24 C26 131.1(3) . . ? N23 C24 C26 122.4(3) . . ? C24 C25 N21 107.7(3) . . ? C24 C25 H25 126.1 . . ? N21 C25 H25 126.1 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 N21 C25 108.5(3) . . ? C22 N21 H21 125.7 . . ? C25 N21 H21 125.7 . . ? C22 N23 C24 108.6(3) . . ? C22 N23 H23 125.7 . . ? C24 N23 H23 125.7 . . ? 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 O1B C1 C2 C3 9.2(5) . . . . ? O1A C1 C2 C3 -171.9(3) . . . . ? C1 C2 C3 C4 179.0(3) . . . . ? C2 C3 C4 C5 179.0(3) . . . . ? C3 C4 C5 C6 171.2(3) . . . . ? C4 C5 C6 C7 64.9(4) . . . . ? C5 C6 C7 C8 179.9(3) . . . . ? C6 C7 C8 O8B 15.9(5) . . . . ? C6 C7 C8 O8A -164.7(3) . . . . ? N23 C24 C25 N21 -0.1(4) . . . . ? C26 C24 C25 N21 -178.6(4) . . . . ? N23 C22 N21 C25 0.0(4) . . . . ? C24 C25 N21 C22 0.1(4) . . . . ? N21 C22 N23 C24 -0.1(4) . . . . ? C25 C24 N23 C22 0.1(4) . . . . ? C26 C24 N23 C22 178.7(3) . . . . ? 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 N21 H21 O8B 0.88 1.81 2.665(4) 164.9 . O1A H1 O8A 0.84 1.75 2.583(3) 171.1 1_454 N23 H23 O8A 0.88 1.80 2.676(4) 173.0 1_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.260 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.058 #============================================================================== data_11 _database_code_depnum_ccdc_archive 'CCDC 745380' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Glutaric Acid & 4-Methylimidazole ; _chemical_name_common 'Glutaric Acid & 4-Methylimidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H14 N2 O4' _chemical_formula_weight 214.22 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.5360(4) _cell_length_b 14.2180(8) _cell_length_c 9.7160(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.571(3) _cell_angle_gamma 90.00 _cell_volume 1034.20(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2417 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9860 _exptl_absorpt_correction_T_max 0.9967 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12026 _diffrn_reflns_av_R_equivalents 0.1295 _diffrn_reflns_av_sigmaI/netI 0.1106 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2460 _reflns_number_gt 1739 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^)+(0.0150P)^2^+0.3727P] 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_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 2460 _refine_ls_number_parameters 281 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0980 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1108 _refine_ls_wR_factor_gt 0.0977 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.004 _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 C1 C 0.1071(5) 0.0859(3) -0.2812(5) 0.0231(9) Uani 1 1 d . . . C2 C 0.0466(5) 0.1075(3) -0.1425(5) 0.0257(10) Uani 1 1 d . . . H2A H 0.1336 0.0799 -0.0695 0.031 Uiso 1 1 calc R . . H2B H -0.0696 0.0762 -0.1370 0.031 Uiso 1 1 calc R . . C3 C 0.0261(5) 0.2117(3) -0.1111(4) 0.0240(9) Uani 1 1 d . . . H3A H -0.0646 0.2397 -0.1810 0.029 Uiso 1 1 calc R . . H3B H 0.1410 0.2442 -0.1175 0.029 Uiso 1 1 calc R . . C4 C -0.0303(5) 0.2262(3) 0.0330(4) 0.0248(10) Uani 1 1 d . . . H4A H -0.1498 0.1980 0.0362 0.030 Uiso 1 1 calc R . . H4B H 0.0546 0.1927 0.1013 0.030 Uiso 1 1 calc R . . C5 C -0.0371(5) 0.3281(3) 0.0745(4) 0.0249(10) Uani 1 1 d . . . O1A O 0.1335(4) 0.1489(2) -0.3651(3) 0.0280(7) Uani 1 1 d . . . O1B O 0.1310(4) -0.0011(2) -0.3064(3) 0.0282(8) Uani 1 1 d . . . O5A O -0.0847(4) 0.3377(2) 0.1998(3) 0.0334(8) Uani 1 1 d . . . H5 H -0.0933 0.3951 0.2183 0.07(2) Uiso 1 1 calc R . . O5B O -0.0021(5) 0.3935(2) 0.0030(4) 0.0367(8) Uani 1 1 d . . . C22 C 0.2516(6) 0.3639(3) 0.5021(5) 0.0253(10) Uani 1 1 d . . . H22 H 0.2859 0.3241 0.4311 0.030 Uiso 1 1 calc R . . C24 C 0.1977(5) 0.4902(3) 0.6222(5) 0.0212(10) Uani 1 1 d . . . C25 C 0.1551(5) 0.4142(3) 0.6935(5) 0.0252(10) Uani 1 1 d . . . H25 H 0.1101 0.4142 0.7809 0.030 Uiso 1 1 calc R . . C26 C 0.1864(5) 0.5929(3) 0.6523(5) 0.0268(10) Uani 1 1 d . . . H26A H 0.1445 0.6017 0.7432 0.040 Uiso 1 1 calc R . . H26B H 0.1026 0.6228 0.5810 0.040 Uiso 1 1 calc R . . H26C H 0.3048 0.6214 0.6523 0.040 Uiso 1 1 calc R . . N21 N 0.1885(4) 0.3362(3) 0.6168(4) 0.0255(9) Uani 1 1 d . . . H21 H 0.1708 0.2774 0.6404 0.025(13) Uiso 1 1 calc R . . N23 N 0.2586(4) 0.4574(3) 0.5034(4) 0.0238(8) Uani 1 1 d . . . H23 H 0.2963 0.4927 0.4383 0.048(16) Uiso 1 1 calc R . . C31 C 0.4226(5) 0.2365(3) 0.1580(5) 0.0231(9) Uani 1 1 d . . . C32 C 0.4540(5) 0.3295(3) 0.0907(4) 0.0205(9) Uani 1 1 d . . . H32A H 0.3722 0.3348 0.0037 0.025 Uiso 1 1 calc R . . H32B H 0.5779 0.3311 0.0660 0.025 Uiso 1 1 calc R . . C33 C 0.4256(5) 0.4134(3) 0.1818(5) 0.0231(9) Uani 1 1 d . . . H33A H 0.3022 0.4115 0.2074 0.028 Uiso 1 1 calc R . . H33B H 0.5085 0.4086 0.2683 0.028 Uiso 1 1 calc R . . C34 C 0.4550(6) 0.5068(3) 0.1134(5) 0.0220(9) Uani 1 1 d . . . H34A H 0.5770 0.5077 0.0848 0.026 Uiso 1 1 calc R . . H34B H 0.3694 0.5123 0.0285 0.026 Uiso 1 1 calc R . . C35 C 0.4335(5) 0.5903(3) 0.2038(5) 0.0234(9) Uani 1 1 d . . . O31A O 0.4437(4) 0.1611(2) 0.0873(3) 0.0262(7) Uani 1 1 d . . . O31B O 0.3755(4) 0.2341(2) 0.2753(3) 0.0300(8) Uani 1 1 d . . . O35A O 0.3868(4) 0.5840(2) 0.3194(3) 0.0305(7) Uani 1 1 d . . . O35B O 0.4654(4) 0.67408(19) 0.1527(4) 0.0294(8) Uani 1 1 d . . . H35 H 0.4911 0.6681 0.0712 0.042(15) Uiso 1 1 calc R . . C42 C 0.7018(5) 0.5483(3) 0.6178(4) 0.0249(10) Uani 1 1 d . . . H42 H 0.7184 0.6120 0.5928 0.030 Uiso 1 1 calc R . . C44 C 0.6923(5) 0.3934(3) 0.6114(4) 0.0221(10) Uani 1 1 d . . . C45 C 0.6367(5) 0.4204(4) 0.7322(5) 0.0257(10) Uani 1 1 d . . . H45 H 0.5998 0.3804 0.8019 0.031 Uiso 1 1 calc R . . C46 C 0.7090(6) 0.2986(3) 0.5512(5) 0.0293(11) Uani 1 1 d . . . H46A H 0.6694 0.2512 0.6142 0.044 Uiso 1 1 calc R . . H46B H 0.8340 0.2869 0.5377 0.044 Uiso 1 1 calc R . . H46C H 0.6346 0.2949 0.4617 0.044 Uiso 1 1 calc R . . N41 N 0.6439(4) 0.5189(3) 0.7354(4) 0.0255(8) Uani 1 1 d . . . H41 H 0.6153 0.5550 0.8031 0.046(15) Uiso 1 1 calc R . . N43 N 0.7319(4) 0.4744(2) 0.5426(4) 0.0217(8) Uani 1 1 d . . . H43 H 0.7714 0.4763 0.4608 0.07(2) 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 0.0226(19) 0.019(2) 0.028(2) 0.002(2) 0.0033(17) -0.0011(18) C2 0.027(2) 0.023(3) 0.029(3) -0.004(2) 0.0074(18) 0.0019(17) C3 0.029(2) 0.021(2) 0.023(2) 0.000(2) 0.0058(18) 0.0004(18) C4 0.031(2) 0.019(3) 0.025(2) -0.0002(19) 0.0096(18) -0.0003(18) C5 0.025(2) 0.027(3) 0.023(2) 0.001(2) 0.0036(17) -0.0005(19) O1A 0.0407(16) 0.0194(16) 0.0259(18) 0.0021(14) 0.0126(14) -0.0027(13) O1B 0.0447(17) 0.0181(17) 0.0244(18) 0.0012(14) 0.0150(14) 0.0029(12) O5A 0.0535(19) 0.0227(18) 0.0273(19) -0.0056(15) 0.0190(15) -0.0016(16) O5B 0.0565(19) 0.026(2) 0.0306(19) -0.0016(17) 0.0175(15) -0.0013(15) C22 0.032(2) 0.020(2) 0.025(2) -0.0019(19) 0.0089(19) -0.0042(18) C24 0.024(2) 0.019(3) 0.022(2) -0.0036(19) 0.0067(17) -0.0023(16) C25 0.030(2) 0.019(2) 0.028(3) -0.001(2) 0.0094(18) -0.001(2) C26 0.037(2) 0.015(2) 0.029(3) -0.004(2) 0.0064(19) 0.0019(19) N21 0.036(2) 0.020(2) 0.022(2) -0.0022(18) 0.0100(16) -0.0032(16) N23 0.0319(19) 0.0190(18) 0.021(2) 0.0006(17) 0.0054(16) -0.0002(15) C31 0.024(2) 0.023(2) 0.023(2) -0.003(2) 0.0048(17) -0.0029(18) C32 0.025(2) 0.017(2) 0.020(2) 0.000(2) 0.0053(16) -0.0013(18) C33 0.029(2) 0.015(2) 0.026(3) -0.004(2) 0.0076(17) -0.0010(19) C34 0.028(2) 0.019(2) 0.019(2) -0.001(2) 0.0050(18) -0.0031(17) C35 0.030(2) 0.016(2) 0.025(2) 0.002(2) 0.0058(18) -0.0007(19) O31A 0.0434(17) 0.0138(14) 0.0238(18) -0.0014(14) 0.0135(14) 0.0025(13) O31B 0.0510(19) 0.0178(17) 0.0243(18) 0.0004(13) 0.0171(14) -0.0006(14) O35A 0.0474(16) 0.0214(16) 0.0254(18) 0.0035(15) 0.0151(14) -0.0009(14) O35B 0.0501(19) 0.0148(15) 0.0260(19) 0.0024(13) 0.0156(15) -0.0031(13) C42 0.030(2) 0.019(2) 0.028(3) -0.003(2) 0.0099(19) -0.0011(17) C44 0.024(2) 0.018(3) 0.024(2) 0.004(2) 0.0022(16) -0.0001(17) C45 0.029(2) 0.024(2) 0.025(3) 0.008(2) 0.0054(18) 0.0003(19) C46 0.039(3) 0.016(2) 0.034(3) -0.001(2) 0.007(2) 0.0023(18) N41 0.0333(19) 0.023(2) 0.022(2) -0.0018(17) 0.0082(16) 0.0012(16) N43 0.0301(18) 0.0151(18) 0.021(2) -0.0005(16) 0.0071(15) -0.0017(15) _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 O1A 1.243(5) . ? C1 O1B 1.278(5) . ? C1 C2 1.503(6) . ? C2 C3 1.523(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.524(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.506(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O5B 1.208(5) . ? C5 O5A 1.315(5) . ? O5A H5 0.8400 . ? C22 N21 1.321(5) . ? C22 N23 1.331(5) . ? C22 H22 0.9500 . ? C24 C25 1.342(6) . ? C24 N23 1.371(5) . ? C24 C26 1.494(6) . ? C25 N21 1.375(6) . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? C31 O31B 1.233(5) . ? C31 O31A 1.293(5) . ? C31 C32 1.506(6) . ? C32 C33 1.515(6) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.513(6) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.496(6) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 O35A 1.218(5) . ? C35 O35B 1.323(5) . ? O35B H35 0.8400 . ? C42 N43 1.314(5) . ? C42 N41 1.336(5) . ? C42 H42 0.9500 . ? C44 C45 1.347(6) . ? C44 N43 1.382(5) . ? C44 C46 1.481(6) . ? C45 N41 1.401(6) . ? C45 H45 0.9500 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? N41 H41 0.8800 . ? N43 H43 0.8800 . ? 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 O1A C1 O1B 122.4(4) . . ? O1A C1 C2 121.9(4) . . ? O1B C1 C2 115.7(4) . . ? C1 C2 C3 115.3(4) . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2B 108.5 . . ? C3 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C4 111.2(4) . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 113.5(4) . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4B 108.9 . . ? C3 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? O5B C5 O5A 123.6(4) . . ? O5B C5 C4 124.8(4) . . ? O5A C5 C4 111.6(4) . . ? C5 O5A H5 109.5 . . ? N21 C22 N23 107.9(4) . . ? N21 C22 H22 126.1 . . ? N23 C22 H22 126.1 . . ? C25 C24 N23 106.5(4) . . ? C25 C24 C26 131.6(4) . . ? N23 C24 C26 121.9(4) . . ? C24 C25 N21 107.5(4) . . ? C24 C25 H25 126.3 . . ? N21 C25 H25 126.3 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 N21 C25 108.8(4) . . ? C22 N21 H21 125.6 . . ? C25 N21 H21 125.6 . . ? C22 N23 C24 109.4(4) . . ? C22 N23 H23 125.3 . . ? C24 N23 H23 125.3 . . ? O31B C31 O31A 122.3(4) . . ? O31B C31 C32 120.1(4) . . ? O31A C31 C32 117.6(3) . . ? C31 C32 C33 113.4(3) . . ? C31 C32 H32A 108.9 . . ? C33 C32 H32A 108.9 . . ? C31 C32 H32B 108.9 . . ? C33 C32 H32B 108.9 . . ? H32A C32 H32B 107.7 . . ? C34 C33 C32 113.4(3) . . ? C34 C33 H33A 108.9 . . ? C32 C33 H33A 108.9 . . ? C34 C33 H33B 108.9 . . ? C32 C33 H33B 108.9 . . ? H33A C33 H33B 107.7 . . ? C35 C34 C33 114.0(3) . . ? C35 C34 H34A 108.7 . . ? C33 C34 H34A 108.7 . . ? C35 C34 H34B 108.7 . . ? C33 C34 H34B 108.7 . . ? H34A C34 H34B 107.6 . . ? O35A C35 O35B 119.8(4) . . ? O35A C35 C34 123.0(4) . . ? O35B C35 C34 117.2(3) . . ? C35 O35B H35 109.5 . . ? N43 C42 N41 108.6(4) . . ? N43 C42 H42 125.7 . . ? N41 C42 H42 125.7 . . ? C45 C44 N43 106.9(4) . . ? C45 C44 C46 130.8(4) . . ? N43 C44 C46 122.3(4) . . ? C44 C45 N41 106.8(4) . . ? C44 C45 H45 126.6 . . ? N41 C45 H45 126.6 . . ? C44 C46 H46A 109.5 . . ? C44 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C44 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C42 N41 C45 108.0(4) . . ? C42 N41 H41 126.0 . . ? C45 N41 H41 126.0 . . ? C42 N43 C44 109.7(3) . . ? C42 N43 H43 125.2 . . ? C44 N43 H43 125.2 . . ? 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 N23 H23 O35A 0.88 1.91 2.787(5) 170.9 . O5A H5 O1B 0.84 1.75 2.555(4) 161.3 2 N21 H21 O1A 0.88 1.85 2.704(4) 163.3 1_556 O35B H35 O31A 0.84 1.67 2.511(4) 175.6 2_655 N43 H43 O1B 0.88 1.77 2.646(4) 169.9 2_655 N41 H41 O31A 0.88 1.93 2.784(4) 163.9 2_656 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.269 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.061 #============================================================================== data_12 _database_code_depnum_ccdc_archive 'CCDC 745381' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Succinic acid & 1,2-dimethylimidazole ; _chemical_name_common 'Succinic acid & 1,2-dimethylimidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H14 N2 O4' _chemical_formula_weight 214.22 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 Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 20.5769(12) _cell_length_b 7.3521(4) _cell_length_c 14.0383(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2123.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8890 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9916 _exptl_absorpt_correction_T_max 0.9968 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43931 _diffrn_reflns_av_R_equivalents 0.1637 _diffrn_reflns_av_sigmaI/netI 0.0612 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2444 _reflns_number_gt 1643 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^)+(0.0490P)^2^+1.7769P] 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_extinction_coef ? _refine_ls_number_reflns 2444 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1161 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.1561 _refine_ls_wR_factor_gt 0.1383 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _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 C1 C 0.56211(12) 0.2711(4) 0.66607(18) 0.0288(6) Uani 1 1 d . . . C2 C 0.51884(12) 0.1712(4) 0.73457(18) 0.0311(6) Uani 1 1 d . . . H2A H 0.5187 0.0407 0.7173 0.037 Uiso 1 1 calc R . . H2B H 0.4739 0.2171 0.7270 0.037 Uiso 1 1 calc R . . C3 C 0.53814(13) 0.1886(4) 0.83846(18) 0.0300(6) Uani 1 1 d . . . H3A H 0.5427 0.3194 0.8539 0.036 Uiso 1 1 calc R . . H3B H 0.5024 0.1396 0.8782 0.036 Uiso 1 1 calc R . . C4 C 0.60058(12) 0.0926(4) 0.86581(19) 0.0291(6) Uani 1 1 d . . . O1A O 0.60443(9) 0.3772(3) 0.68932(13) 0.0378(5) Uani 1 1 d . . . O1B O 0.54796(9) 0.2313(3) 0.57668(13) 0.0349(5) Uani 1 1 d . . . H1 H 0.5757 0.2786 0.5405 0.068(12) Uiso 1 1 calc R . . O4A O 0.62345(9) 0.1348(3) 0.94797(12) 0.0361(5) Uani 1 1 d . . . O4B O 0.62504(9) -0.0219(3) 0.81241(13) 0.0364(5) Uani 1 1 d . . . C22 C 0.71067(13) 0.5402(4) 0.95590(19) 0.0339(6) Uani 1 1 d . . . C24 C 0.74885(15) 0.4887(4) 1.10051(19) 0.0364(7) Uani 1 1 d . . . H24 H 0.7774 0.4546 1.1506 0.044 Uiso 1 1 calc R . . C25 C 0.68822(14) 0.5515(4) 1.1099(2) 0.0383(7) Uani 1 1 d . . . H25 H 0.6655 0.5701 1.1680 0.046 Uiso 1 1 calc R . . C26 C 0.60115(13) 0.6610(4) 0.9977(2) 0.0481(8) Uani 1 1 d . . . H26A H 0.5964 0.6762 0.9287 0.072 Uiso 1 1 calc R . . H26B H 0.5970 0.7796 1.0290 0.072 Uiso 1 1 calc R . . H26C H 0.5673 0.5789 1.0213 0.072 Uiso 1 1 calc R . . C27 C 0.70486(15) 0.5477(4) 0.85174(19) 0.0430(7) Uani 1 1 d . . . H27A H 0.6749 0.4529 0.8301 0.064 Uiso 1 1 calc R . . H27B H 0.7477 0.5282 0.8229 0.064 Uiso 1 1 calc R . . H27C H 0.6882 0.6672 0.8328 0.064 Uiso 1 1 calc R . . N21 N 0.66477(10) 0.5844(3) 1.01855(16) 0.0326(5) Uani 1 1 d . . . N23 N 0.76225(11) 0.4826(3) 1.00354(16) 0.0336(5) Uani 1 1 d . . . H23 H 0.7991 0.4463 0.9779 0.071(12) 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 0.0257(13) 0.0317(14) 0.0290(14) 0.0009(11) -0.0028(11) 0.0050(12) C2 0.0288(14) 0.0328(14) 0.0317(14) 0.0013(12) -0.0015(11) -0.0024(11) C3 0.0301(14) 0.0326(14) 0.0272(13) -0.0008(11) -0.0005(11) 0.0010(11) C4 0.0292(14) 0.0305(14) 0.0277(14) 0.0045(11) 0.0036(11) 0.0014(11) O1A 0.0383(11) 0.0408(11) 0.0343(11) -0.0038(9) -0.0024(8) -0.0102(9) O1B 0.0370(11) 0.0424(11) 0.0254(10) -0.0008(8) -0.0015(8) -0.0104(9) O4A 0.0350(10) 0.0471(12) 0.0261(10) -0.0025(8) -0.0045(8) 0.0074(9) O4B 0.0402(11) 0.0386(11) 0.0304(10) -0.0035(8) 0.0026(9) 0.0115(9) C22 0.0334(15) 0.0296(14) 0.0387(16) 0.0010(12) -0.0008(12) -0.0077(12) C24 0.0411(16) 0.0357(15) 0.0325(15) 0.0019(12) -0.0063(13) -0.0022(13) C25 0.0429(16) 0.0389(16) 0.0332(16) -0.0003(12) 0.0072(13) -0.0005(14) C26 0.0336(16) 0.0475(18) 0.063(2) 0.0127(16) 0.0067(15) 0.0096(14) C27 0.0427(17) 0.0511(18) 0.0351(16) -0.0014(14) 0.0001(13) -0.0052(14) N21 0.0284(12) 0.0302(12) 0.0390(13) 0.0011(10) 0.0061(10) -0.0018(10) N23 0.0298(12) 0.0319(12) 0.0391(13) -0.0012(10) 0.0020(11) 0.0009(10) _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 O1A 1.214(3) . ? C1 O1B 1.321(3) . ? C1 C2 1.502(4) . ? C2 C3 1.517(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.516(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O4B 1.234(3) . ? C4 O4A 1.284(3) . ? O1B H1 0.8400 . ? C22 N23 1.324(3) . ? C22 N21 1.331(3) . ? C22 C27 1.468(4) . ? C24 C25 1.337(4) . ? C24 N23 1.390(3) . ? C24 H24 0.9500 . ? C25 N21 1.392(4) . ? C25 H25 0.9500 . ? C26 N21 1.455(3) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? N23 H23 0.8800 . ? 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 O1A C1 O1B 123.8(2) . . ? O1A C1 C2 124.6(2) . . ? O1B C1 C2 111.7(2) . . ? C1 C2 C3 114.8(2) . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? C3 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C4 C3 C2 115.2(2) . . ? C4 C3 H3A 108.5 . . ? C2 C3 H3A 108.5 . . ? C4 C3 H3B 108.5 . . ? C2 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? O4B C4 O4A 124.1(2) . . ? O4B C4 C3 120.6(2) . . ? O4A C4 C3 115.2(2) . . ? C1 O1B H1 109.5 . . ? N23 C22 N21 108.3(2) . . ? N23 C22 C27 125.5(3) . . ? N21 C22 C27 126.2(3) . . ? C25 C24 N23 107.1(2) . . ? C25 C24 H24 126.5 . . ? N23 C24 H24 126.5 . . ? C24 C25 N21 107.0(2) . . ? C24 C25 H25 126.5 . . ? N21 C25 H25 126.5 . . ? N21 C26 H26A 109.5 . . ? N21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C22 N21 C25 108.7(2) . . ? C22 N21 C26 126.9(2) . . ? C25 N21 C26 124.4(2) . . ? C22 N23 C24 109.0(2) . . ? C22 N23 H23 125.5 . . ? C24 N23 H23 125.5 . . ? 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 O1B H1 O4A 0.84 1.75 2.578(3) 169.2 7_565 N23 H23 O4A 0.88 1.75 2.624(3) 169.7 2_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.335 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.055 #============================================================================== data_13 _database_code_depnum_ccdc_archive 'CCDC 745382' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Glutaric acid & 1,2-dimethylimidazole ; _chemical_name_common 'Glutaric acid & 1,2-dimethylimidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 N2 O4' _chemical_formula_weight 228.25 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna21 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' _cell_length_a 10.4056(16) _cell_length_b 22.888(4) _cell_length_c 4.6392(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1104.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1195 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9873 _exptl_absorpt_correction_T_max 0.9936 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5897 _diffrn_reflns_av_R_equivalents 0.1342 _diffrn_reflns_av_sigmaI/netI 0.1024 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1092 _reflns_number_gt 752 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.1211P)^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_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 1092 _refine_ls_number_parameters 148 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1159 _refine_ls_R_factor_gt 0.0748 _refine_ls_wR_factor_ref 0.2082 _refine_ls_wR_factor_gt 0.1862 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.002 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 0.4727(6) 0.6732(3) 0.2614(19) 0.0291(17) Uani 1 1 d . . . C2 C 0.3756(7) 0.7007(3) 0.0627(17) 0.0322(19) Uani 1 1 d . . . H2A H 0.4224 0.7206 -0.0949 0.039 Uiso 1 1 calc R . . H2B H 0.3281 0.7310 0.1716 0.039 Uiso 1 1 calc R . . C3 C 0.2778(6) 0.6590(3) -0.072(2) 0.0332(18) Uani 1 1 d . . . H3A H 0.3226 0.6307 -0.1983 0.040 Uiso 1 1 calc R . . H3B H 0.2334 0.6368 0.0819 0.040 Uiso 1 1 calc R . . C4 C 0.1800(7) 0.6931(3) -0.2468(19) 0.0339(18) Uani 1 1 d . . . H4A H 0.1336 0.7201 -0.1162 0.041 Uiso 1 1 calc R . . H4B H 0.2262 0.7172 -0.3905 0.041 Uiso 1 1 calc R . . C5 C 0.0824(6) 0.6554(3) -0.4031(17) 0.0285(17) Uani 1 1 d . . . O1A O 0.4776(4) 0.61904(19) 0.2827(13) 0.0360(14) Uani 1 1 d . . . O1B O 0.5438(4) 0.70762(19) 0.4062(13) 0.0375(14) Uani 1 1 d . . . O5A O 0.0728(5) 0.60343(19) -0.3686(14) 0.0383(14) Uani 1 1 d . . . O5B O 0.0033(4) 0.6831(2) -0.5781(14) 0.0371(13) Uani 1 1 d . . . H5 H 0.0192 0.7191 -0.5735 0.056 Uiso 1 1 calc R . . C22 C 0.2779(6) 0.4126(3) 0.3307(18) 0.0289(18) Uani 1 1 d . . . C24 C 0.3635(6) 0.4943(3) 0.166(2) 0.0306(18) Uani 1 1 d . . . H24 H 0.4159 0.5205 0.0588 0.037 Uiso 1 1 calc R . . C25 C 0.2734(7) 0.5091(3) 0.3557(17) 0.0334(19) Uani 1 1 d . . . H25 H 0.2506 0.5477 0.4115 0.040 Uiso 1 1 calc R . . C26 C 0.1130(6) 0.4537(3) 0.6628(18) 0.0332(19) Uani 1 1 d . . . H26A H 0.0363 0.4388 0.5648 0.050 Uiso 1 1 calc R . . H26B H 0.0948 0.4925 0.7426 0.050 Uiso 1 1 calc R . . H26C H 0.1369 0.4271 0.8192 0.050 Uiso 1 1 calc R . . C27 C 0.2515(7) 0.3506(3) 0.379(2) 0.037(2) Uani 1 1 d . . . H27A H 0.3191 0.3271 0.2882 0.056 Uiso 1 1 calc R . . H27B H 0.1682 0.3406 0.2936 0.056 Uiso 1 1 calc R . . H27C H 0.2496 0.3427 0.5861 0.056 Uiso 1 1 calc R . . N21 N 0.2188(6) 0.4579(2) 0.4570(15) 0.0324(15) Uani 1 1 d . . . N23 N 0.3671(5) 0.4344(2) 0.1523(14) 0.0321(15) Uani 1 1 d . . . H23 H 0.4194 0.4137 0.0440 0.039 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 0.025(3) 0.024(4) 0.038(4) -0.006(4) -0.004(4) -0.002(3) C2 0.042(4) 0.025(4) 0.030(5) 0.005(3) 0.001(4) 0.000(3) C3 0.035(3) 0.028(4) 0.036(5) 0.002(4) 0.000(4) 0.000(3) C4 0.042(4) 0.023(4) 0.037(5) -0.003(4) 0.008(4) -0.006(3) C5 0.020(3) 0.035(4) 0.030(4) 0.001(4) 0.003(4) 0.007(3) O1A 0.045(3) 0.019(2) 0.043(3) 0.002(2) -0.004(3) 0.003(2) O1B 0.044(3) 0.026(3) 0.043(3) -0.002(3) -0.012(3) 0.003(2) O5A 0.050(3) 0.017(3) 0.048(4) 0.000(2) -0.006(3) 0.002(2) O5B 0.046(3) 0.022(2) 0.043(3) -0.002(3) -0.011(3) 0.000(2) C22 0.023(3) 0.026(4) 0.038(5) 0.002(3) -0.010(4) -0.001(3) C24 0.023(3) 0.023(4) 0.046(5) -0.003(4) -0.002(4) 0.003(3) C25 0.057(4) 0.010(3) 0.033(5) 0.001(3) -0.003(4) 0.003(3) C26 0.041(4) 0.025(4) 0.034(5) -0.004(4) -0.004(4) 0.001(3) C27 0.045(4) 0.024(4) 0.044(5) 0.002(3) 0.000(4) 0.000(3) N21 0.038(3) 0.025(3) 0.035(4) -0.006(3) 0.000(3) 0.003(2) N23 0.040(3) 0.023(3) 0.033(4) -0.009(3) -0.001(3) 0.003(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1A 1.245(8) . ? C1 O1B 1.272(8) . ? C1 C2 1.505(10) . ? C2 C3 1.528(10) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.518(10) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.517(10) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O5A 1.205(8) . ? C5 O5B 1.318(8) . ? O5B H5 0.8400 . ? C22 N23 1.340(9) . ? C22 N21 1.341(9) . ? C22 C27 1.461(9) . ? C24 C25 1.331(10) . ? C24 N23 1.374(8) . ? C24 H24 0.9500 . ? C25 N21 1.384(9) . ? C25 H25 0.9500 . ? C26 N21 1.460(9) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? N23 H23 0.8800 . ? 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 O1A C1 O1B 123.4(7) . . ? O1A C1 C2 119.5(6) . . ? O1B C1 C2 117.1(6) . . ? C1 C2 C3 115.9(6) . . ? C1 C2 H2A 108.3 . . ? C3 C2 H2A 108.3 . . ? C1 C2 H2B 108.3 . . ? C3 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? C4 C3 C2 110.1(6) . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? C4 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.2 . . ? C5 C4 C3 114.3(6) . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4A 108.7 . . ? C5 C4 H4B 108.7 . . ? C3 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? O5A C5 O5B 120.4(6) . . ? O5A C5 C4 123.6(7) . . ? O5B C5 C4 116.0(6) . . ? C5 O5B H5 109.5 . . ? N23 C22 N21 107.4(6) . . ? N23 C22 C27 125.8(6) . . ? N21 C22 C27 126.7(7) . . ? C25 C24 N23 107.6(6) . . ? C25 C24 H24 126.2 . . ? N23 C24 H24 126.2 . . ? C24 C25 N21 107.4(6) . . ? C24 C25 H25 126.3 . . ? N21 C25 H25 126.3 . . ? N21 C26 H26A 109.5 . . ? N21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C22 N21 C25 108.6(6) . . ? C22 N21 C26 125.5(6) . . ? C25 N21 C26 125.9(6) . . ? C22 N23 C24 109.0(6) . . ? C22 N23 H23 125.5 . . ? C24 N23 H23 125.5 . . ? 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 O5B H5 O1B 0.84 1.70 2.537(6) 174.7 3_464 N23 H23 O1A 0.88 1.78 2.655(8) 170.7 2_664 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.356 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.094 #============================================================================== data_14 _database_code_depnum_ccdc_archive 'CCDC 745383' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Methyloxalate & 1-methylimidazolium ; _chemical_name_common 'Methyloxalate & 1-methylimidazolium' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H10 N2 O4' _chemical_formula_weight 186.17 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_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.4624(4) _cell_length_b 18.8186(10) _cell_length_c 7.1493(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.878(4) _cell_angle_gamma 90.00 _cell_volume 859.03(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2011 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9929 _exptl_absorpt_correction_T_max 0.9988 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11322 _diffrn_reflns_av_R_equivalents 0.1031 _diffrn_reflns_av_sigmaI/netI 0.0812 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1972 _reflns_number_gt 1279 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^)+(0.0329P)^2^+0.5107P] 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_extinction_coef ? _refine_ls_number_reflns 1972 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1145 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1230 _refine_ls_wR_factor_gt 0.1067 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 C1 C 0.4337(4) 0.56521(12) 0.6478(3) 0.0195(5) Uani 1 1 d . . . C2 C 0.6509(4) 0.59772(13) 0.7321(3) 0.0203(5) Uani 1 1 d . . . C3 C 0.1090(4) 0.58775(14) 0.4594(4) 0.0272(6) Uani 1 1 d . . . H3A H 0.1182 0.5450 0.3828 0.041 Uiso 1 1 calc R . . H3B H 0.0363 0.6253 0.3800 0.041 Uiso 1 1 calc R . . H3C H 0.0312 0.5769 0.5632 0.041 Uiso 1 1 calc R . . O1A O 0.3773(3) 0.50644(9) 0.6826(2) 0.0266(4) Uani 1 1 d . . . O1B O 0.3184(2) 0.61160(8) 0.5367(2) 0.0228(4) Uani 1 1 d . . . O2A O 0.7714(2) 0.55453(8) 0.8312(2) 0.0251(4) Uani 1 1 d . . . O2B O 0.6838(3) 0.66024(9) 0.6971(2) 0.0279(4) Uani 1 1 d . . . C22 C 1.3045(3) 0.60304(12) 1.0561(3) 0.0190(5) Uani 1 1 d . . . H22 H 1.3420 0.5552 1.0874 0.023 Uiso 1 1 calc R . . C24 C 1.1270(4) 0.69730(13) 0.9453(3) 0.0240(6) Uani 1 1 d . . . H24 H 1.0166 0.7266 0.8851 0.029 Uiso 1 1 calc R . . C25 C 1.3182(4) 0.71957(13) 1.0289(4) 0.0246(6) Uani 1 1 d . . . H25 H 1.3680 0.7671 1.0384 0.029 Uiso 1 1 calc R . . C26 C 1.6411(4) 0.65895(13) 1.2006(3) 0.0252(6) Uani 1 1 d . . . H26A H 1.6394 0.6710 1.3337 0.038 Uiso 1 1 calc R . . H26B H 1.7257 0.6939 1.1445 0.038 Uiso 1 1 calc R . . H26C H 1.7017 0.6115 1.1924 0.038 Uiso 1 1 calc R . . N21 N 1.4261(3) 0.65961(10) 1.0975(3) 0.0187(4) Uani 1 1 d . . . N23 N 1.1217(3) 0.62492(10) 0.9634(3) 0.0216(5) Uani 1 1 d . . . H23 H 1.0147 0.5974 0.9206 0.035(8) 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 0.0240(13) 0.0165(13) 0.0179(12) -0.0017(10) 0.0030(10) 0.0013(10) C2 0.0198(13) 0.0189(13) 0.0216(12) 0.0001(11) 0.0015(10) 0.0007(10) C3 0.0175(13) 0.0273(14) 0.0337(15) -0.0007(12) -0.0057(11) -0.0030(11) O1A 0.0260(10) 0.0215(9) 0.0307(10) 0.0042(8) -0.0011(8) -0.0042(8) O1B 0.0179(9) 0.0183(9) 0.0302(10) 0.0021(7) -0.0028(7) -0.0006(7) O2A 0.0223(9) 0.0196(9) 0.0303(10) 0.0027(8) -0.0053(7) 0.0003(7) O2B 0.0264(10) 0.0185(9) 0.0355(10) 0.0028(8) -0.0053(8) -0.0038(7) C22 0.0205(12) 0.0150(12) 0.0209(13) 0.0001(10) 0.0017(10) 0.0007(10) C24 0.0254(13) 0.0179(13) 0.0273(14) 0.0049(11) -0.0003(11) 0.0021(10) C25 0.0255(14) 0.0156(13) 0.0312(15) 0.0005(11) 0.0000(11) 0.0001(10) C26 0.0183(13) 0.0279(14) 0.0274(13) -0.0016(11) -0.0026(10) -0.0015(11) N21 0.0178(10) 0.0180(10) 0.0194(10) -0.0002(9) -0.0006(8) -0.0004(8) N23 0.0204(11) 0.0209(11) 0.0217(11) 0.0012(9) -0.0025(9) -0.0029(9) _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 O1A 1.202(3) . ? C1 O1B 1.329(3) . ? C1 C2 1.564(3) . ? C2 O2B 1.228(3) . ? C2 O2A 1.264(3) . ? C3 O1B 1.452(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C22 N23 1.328(3) . ? C22 N21 1.329(3) . ? C22 H22 0.9500 . ? C24 C25 1.353(3) . ? C24 N23 1.369(3) . ? C24 H24 0.9500 . ? C25 N21 1.376(3) . ? C25 H25 0.9500 . ? C26 N21 1.469(3) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N23 H23 0.8800 . ? 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 O1A C1 O1B 124.6(2) . . ? O1A C1 C2 124.2(2) . . ? O1B C1 C2 111.1(2) . . ? O2B C2 O2A 128.3(2) . . ? O2B C2 C1 118.0(2) . . ? O2A C2 C1 113.8(2) . . ? O1B C3 H3A 109.5 . . ? O1B C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? O1B C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 O1B C3 115.36(18) . . ? N23 C22 N21 108.2(2) . . ? N23 C22 H22 125.9 . . ? N21 C22 H22 125.9 . . ? C25 C24 N23 107.5(2) . . ? C25 C24 H24 126.2 . . ? N23 C24 H24 126.2 . . ? C24 C25 N21 106.3(2) . . ? C24 C25 H25 126.8 . . ? N21 C25 H25 126.8 . . ? N21 C26 H26A 109.5 . . ? N21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 N21 C25 109.13(19) . . ? C22 N21 C26 125.87(19) . . ? C25 N21 C26 125.0(2) . . ? C22 N23 C24 108.8(2) . . ? C22 N23 H23 125.6 . . ? C24 N23 H23 125.6 . . ? 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 N23 H23 O2A 0.88 1.80 2.667(3) 170.5 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.225 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.060 #============================================================================== data_15 _database_code_depnum_ccdc_archive 'CCDC 745384' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Oxalic acid & 2-methylimidazole ; _chemical_name_common 'Oxalic acid & 2-methylimidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H14 N4 O4' _chemical_formula_weight 254.25 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.3293(19) _cell_length_b 13.1137(16) _cell_length_c 14.023(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2451.2(6) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5072 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9892 _exptl_absorpt_correction_T_max 0.9957 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23377 _diffrn_reflns_av_R_equivalents 0.1299 _diffrn_reflns_av_sigmaI/netI 0.0590 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2154 _reflns_number_gt 1698 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0435P)^2^+3.2219P] 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_extinction_coef ? _refine_ls_number_reflns 2154 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1189 _refine_ls_R_factor_gt 0.0906 _refine_ls_wR_factor_ref 0.1693 _refine_ls_wR_factor_gt 0.1593 _refine_ls_goodness_of_fit_ref 1.244 _refine_ls_restrained_S_all 1.244 _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 C1 C 0.1397(3) 0.1274(3) 0.0359(3) 0.0273(9) Uani 1 1 d . . . C2 C 0.2309(3) 0.1374(3) -0.0340(3) 0.0289(9) Uani 1 1 d . . . O1A O 0.16047(18) 0.1045(2) 0.12142(17) 0.0326(7) Uani 1 1 d . . . O1B O 0.05363(19) 0.1416(2) 0.00347(17) 0.0342(7) Uani 1 1 d . . . O2A O 0.31402(19) 0.1043(2) -0.00556(17) 0.0342(7) Uani 1 1 d . . . O2B O 0.21352(19) 0.1766(2) -0.11372(17) 0.0336(7) Uani 1 1 d . . . C22 C 0.0308(3) -0.0855(3) -0.3090(3) 0.0297(9) Uani 1 1 d . . . C24 C 0.1760(3) -0.0675(3) -0.2346(3) 0.0309(9) Uani 1 1 d . . . H24 H 0.2460 -0.0607 -0.2236 0.037 Uiso 1 1 calc R . . C25 C 0.1033(3) -0.0698(3) -0.1680(3) 0.0328(10) Uani 1 1 d . . . H25 H 0.1122 -0.0640 -0.1010 0.039 Uiso 1 1 calc R . . C26 C -0.0463(3) -0.0964(3) -0.3857(3) 0.0350(10) Uani 1 1 d . . . H26A H -0.0814 -0.0314 -0.3942 0.052 Uiso 1 1 calc R . . H26B H -0.0947 -0.1492 -0.3676 0.052 Uiso 1 1 calc R . . H26C H -0.0134 -0.1157 -0.4456 0.052 Uiso 1 1 calc R . . N21 N 0.0135(2) -0.0820(2) -0.2154(2) 0.0281(7) Uani 1 1 d . . . H21 H -0.0459 -0.0866 -0.1883 0.052(14) Uiso 1 1 calc R . . N23 N 0.1293(2) -0.0770(2) -0.3221(2) 0.0295(8) Uani 1 1 d . . . H23 H 0.1598 -0.0774 -0.3778 0.038(12) Uiso 1 1 calc R . . C32 C -0.0995(3) 0.3364(3) 0.3064(3) 0.0274(9) Uani 1 1 d . . . C34 C -0.0224(3) 0.3256(3) 0.1672(3) 0.0303(9) Uani 1 1 d . . . H34 H -0.0113 0.3202 0.1005 0.036 Uiso 1 1 calc R . . C35 C 0.0487(3) 0.3311(3) 0.2353(3) 0.0294(9) Uani 1 1 d . . . H35 H 0.1193 0.3304 0.2257 0.035 Uiso 1 1 calc R . . C36 C -0.1780(3) 0.3412(3) 0.3813(3) 0.0356(10) Uani 1 1 d . . . H36A H -0.1477 0.3278 0.4437 0.053 Uiso 1 1 calc R . . H36B H -0.2296 0.2898 0.3682 0.053 Uiso 1 1 calc R . . H36C H -0.2086 0.4091 0.3814 0.053 Uiso 1 1 calc R . . N31 N -0.0004(2) 0.3378(2) 0.3217(2) 0.0282(8) Uani 1 1 d . . . H31 H 0.0287 0.3424 0.3778 0.065(16) Uiso 1 1 calc R . . N33 N -0.1142(2) 0.3293(2) 0.2123(2) 0.0289(8) Uani 1 1 d . . . H33 H -0.1729 0.3274 0.1838 0.052(14) 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 0.025(2) 0.028(2) 0.029(2) -0.0033(17) -0.0030(18) -0.0017(16) C2 0.029(2) 0.029(2) 0.029(2) -0.0046(17) -0.0021(18) 0.0024(17) O1A 0.0276(15) 0.0476(16) 0.0225(14) 0.0058(12) -0.0014(12) 0.0006(12) O1B 0.0248(15) 0.0542(17) 0.0237(13) 0.0016(13) -0.0003(12) 0.0020(13) O2A 0.0264(15) 0.0503(17) 0.0257(14) 0.0030(13) 0.0007(12) 0.0089(13) O2B 0.0288(15) 0.0481(17) 0.0238(14) 0.0061(13) 0.0001(12) 0.0012(12) C22 0.030(2) 0.026(2) 0.034(2) -0.0002(17) 0.0051(18) 0.0021(17) C24 0.028(2) 0.030(2) 0.035(2) -0.0013(18) -0.0011(18) -0.0015(16) C25 0.033(2) 0.032(2) 0.034(2) -0.0025(18) 0.0022(19) -0.0001(18) C26 0.033(2) 0.040(2) 0.033(2) -0.0025(18) 0.0031(19) 0.0024(19) N21 0.0300(19) 0.0284(17) 0.0258(17) -0.0024(13) 0.0074(15) -0.0029(14) N23 0.0292(19) 0.0289(18) 0.0305(19) 0.0014(14) 0.0083(15) -0.0009(14) C32 0.031(2) 0.023(2) 0.029(2) 0.0027(16) -0.0051(17) -0.0010(16) C34 0.034(2) 0.028(2) 0.029(2) 0.0044(17) 0.0015(18) 0.0019(17) C35 0.029(2) 0.0273(19) 0.032(2) 0.0012(17) -0.0015(18) 0.0008(16) C36 0.034(2) 0.038(2) 0.035(2) 0.0014(19) -0.0016(19) -0.0017(19) N31 0.0278(18) 0.0290(17) 0.0278(18) -0.0008(13) -0.0046(15) -0.0017(14) N33 0.033(2) 0.0312(18) 0.0227(17) 0.0008(13) -0.0051(15) -0.0025(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1B 1.249(4) . ? C1 O1A 1.266(4) . ? C1 C2 1.567(5) . ? C2 O2B 1.252(4) . ? C2 O2A 1.255(4) . ? C22 N23 1.330(5) . ? C22 N21 1.333(5) . ? C22 C26 1.495(5) . ? C24 C25 1.346(5) . ? C24 N23 1.382(5) . ? C24 H24 0.9500 . ? C25 N21 1.379(5) . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? C32 N33 1.337(5) . ? C32 N31 1.338(5) . ? C32 C36 1.483(5) . ? C34 C35 1.347(5) . ? C34 N33 1.378(5) . ? C34 H34 0.9500 . ? C35 N31 1.380(5) . ? C35 H35 0.9500 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? N31 H31 0.8800 . ? N33 H33 0.8800 . ? 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 O1B C1 O1A 125.5(3) . . ? O1B C1 C2 118.2(3) . . ? O1A C1 C2 116.3(3) . . ? O2B C2 O2A 126.1(4) . . ? O2B C2 C1 116.7(3) . . ? O2A C2 C1 117.2(3) . . ? N23 C22 N21 107.7(3) . . ? N23 C22 C26 125.9(3) . . ? N21 C22 C26 126.3(3) . . ? C25 C24 N23 106.8(3) . . ? C25 C24 H24 126.6 . . ? N23 C24 H24 126.6 . . ? C24 C25 N21 107.1(3) . . ? C24 C25 H25 126.5 . . ? N21 C25 H25 126.5 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 N21 C25 109.1(3) . . ? C22 N21 H21 125.4 . . ? C25 N21 H21 125.4 . . ? C22 N23 C24 109.2(3) . . ? C22 N23 H23 125.4 . . ? C24 N23 H23 125.4 . . ? N33 C32 N31 107.6(3) . . ? N33 C32 C36 126.8(3) . . ? N31 C32 C36 125.6(3) . . ? C35 C34 N33 107.3(3) . . ? C35 C34 H34 126.4 . . ? N33 C34 H34 126.4 . . ? C34 C35 N31 107.0(3) . . ? C34 C35 H35 126.5 . . ? N31 C35 H35 126.5 . . ? C32 C36 H36A 109.5 . . ? C32 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C32 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C32 N31 C35 109.1(3) . . ? C32 N31 H31 125.5 . . ? C35 N31 H31 125.5 . . ? C32 N33 C34 109.0(3) . . ? C32 N33 H33 125.5 . . ? C34 N33 H33 125.5 . . ? 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 N21 H21 O1A 0.88 1.81 2.683(4) 173.3 5 N23 H23 O2A 0.88 1.86 2.705(4) 160.4 2_554 N23 H23 O1A 0.88 2.42 2.934(4) 117.6 2_554 N31 H31 O1B 0.88 1.80 2.663(4) 164.2 7_566 N31 H31 O2B 0.88 2.48 2.998(4) 118.3 7_566 N33 H33 O2B 0.88 1.81 2.682(4) 174.1 4_455 N33 H33 O2A 0.88 2.66 3.175(4) 118.4 4_455 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.241 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.060 #============================================================================== data_16 _database_code_depnum_ccdc_archive 'CCDC 745385' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Oxalic acid & 4-methylimidazole hydrate ; _chemical_name_common 'Oxalic acid & 4-methylimidazole hydrate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 N4 O5' _chemical_formula_weight 272.27 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_H-M C2/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 9.1937(6) _cell_length_b 13.5734(6) _cell_length_c 10.5047(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.252(4) _cell_angle_gamma 90.00 _cell_volume 1293.83(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2929 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9833 _exptl_absorpt_correction_T_max 0.9977 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14887 _diffrn_reflns_av_R_equivalents 0.1136 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1488 _reflns_number_gt 1187 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^)+(0.0361P)^2^+1.4019P] 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 1488 _refine_ls_number_parameters 92 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1131 _refine_ls_wR_factor_gt 0.1051 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.079 _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 C1 C 0.21087(18) 0.29820(12) 0.51825(16) 0.0175(4) Uani 1 1 d . . . O1A O 0.18211(14) 0.30242(9) 0.63078(12) 0.0220(3) Uani 1 1 d . . . O1B O 0.18420(14) 0.36289(9) 0.43324(12) 0.0240(3) Uani 1 1 d . . . C22 C 0.1926(2) 0.41823(13) 1.14760(17) 0.0218(4) Uani 1 1 d . . . H22 H 0.1208 0.4454 1.1931 0.026 Uiso 1 1 calc R . . C24 C 0.33822(18) 0.39521(13) 1.00196(17) 0.0200(4) Uani 1 1 d . . . C25 C 0.36522(19) 0.32356(14) 1.09259(17) 0.0229(4) Uani 1 1 d . . . H25 H 0.4351 0.2718 1.0943 0.028 Uiso 1 1 calc R . . C26 C 0.4023(2) 0.41452(15) 0.88334(18) 0.0279(4) Uani 1 1 d . . . H26A H 0.4934 0.3765 0.8862 0.042 Uiso 1 1 calc R . . H26B H 0.4242 0.4849 0.8780 0.042 Uiso 1 1 calc R . . H26C H 0.3316 0.3949 0.8075 0.042 Uiso 1 1 calc R . . N21 N 0.27324(16) 0.33931(11) 1.18157(14) 0.0221(4) Uani 1 1 d . . . H21 H 0.2689 0.3027 1.2500 0.026 Uiso 1 1 calc R . . N23 N 0.22903(16) 0.45326(11) 1.03898(14) 0.0201(3) Uani 1 1 d . . . H23 H 0.1896 0.5054 0.9971 0.024 Uiso 1 1 calc R . . O1W O 0.0000 0.42314(13) 0.7500 0.0300(5) Uani 1 2 d SD . . H1W H -0.0699(10) 0.3888(19) 0.783(3) 0.078(10) 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 0.0179(8) 0.0169(8) 0.0184(8) -0.0021(7) 0.0050(7) -0.0027(6) O1A 0.0289(7) 0.0199(6) 0.0194(7) 0.0001(5) 0.0103(5) 0.0029(5) O1B 0.0349(7) 0.0172(6) 0.0210(6) 0.0016(5) 0.0078(5) 0.0036(5) C22 0.0245(9) 0.0202(9) 0.0218(9) -0.0013(7) 0.0073(7) 0.0007(7) C24 0.0188(8) 0.0216(9) 0.0195(9) -0.0018(7) 0.0030(7) -0.0020(7) C25 0.0227(9) 0.0238(9) 0.0231(9) -0.0008(7) 0.0061(7) 0.0035(7) C26 0.0256(9) 0.0361(11) 0.0230(10) 0.0020(8) 0.0068(8) -0.0023(8) N21 0.0268(8) 0.0208(8) 0.0192(7) 0.0029(6) 0.0058(6) 0.0013(6) N23 0.0234(7) 0.0173(7) 0.0201(8) 0.0015(6) 0.0052(6) 0.0010(6) O1W 0.0314(10) 0.0190(10) 0.0451(12) 0.000 0.0226(9) 0.000 _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 O1B 1.248(2) . ? C1 O1A 1.253(2) . ? C1 C1 1.570(3) 7_556 ? C22 N21 1.319(2) . ? C22 N23 1.328(2) . ? C22 H22 0.9500 . ? C24 C25 1.356(3) . ? C24 N23 1.380(2) . ? C24 C26 1.485(2) . ? C25 N21 1.374(2) . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? O1W H1W 0.905(15) . ? 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 O1B C1 O1A 126.55(15) . . ? O1B C1 C1 117.16(18) . 7_556 ? O1A C1 C1 116.29(18) . 7_556 ? N21 C22 N23 108.37(15) . . ? N21 C22 H22 125.8 . . ? N23 C22 H22 125.8 . . ? C25 C24 N23 105.72(15) . . ? C25 C24 C26 131.56(17) . . ? N23 C24 C26 122.71(16) . . ? C24 C25 N21 107.63(15) . . ? C24 C25 H25 126.2 . . ? N21 C25 H25 126.2 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 N21 C25 108.83(15) . . ? C22 N21 H21 125.6 . . ? C25 N21 H21 125.6 . . ? C22 N23 C24 109.45(15) . . ? C22 N23 H23 125.3 . . ? C24 N23 H23 125.3 . . ? 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 N21 H21 O1A 0.88 1.90 2.7376(19) 157.4 7_557 N21 H21 O1B 0.88 2.34 2.9083(19) 122.7 1_556 N23 H23 O1B 0.88 1.91 2.7358(19) 156.2 6_566 O1W H1W O1A 0.905(15) 1.889(18) 2.7804(16) 168.1(16) 2_556 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.297 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.068 #============================================================================== data_17 _database_code_depnum_ccdc_archive 'CCDC 745386' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Malonic acid & imidazole ; _chemical_name_common 'Malonic acid & imidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 N6 O8' _chemical_formula_weight 412.37 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 6.9980(3) _cell_length_b 8.3790(3) _cell_length_c 9.2500(3) _cell_angle_alpha 116.302(2) _cell_angle_beta 101.825(2) _cell_angle_gamma 91.149(2) _cell_volume 472.10(3) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5405 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 216 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9777 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10823 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2155 _reflns_number_gt 1691 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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. Short contact O1B..C35 is due to the disorder of the imidazole ring resulting in a strong C-H...O hydrogen bond. All the hydrogen atoms have been fixed as riding in calculated positions, except for H3b which is shared between two malonate molecules and is located on a special position. ; _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^)+(0.0447P)^2^+0.2219P] 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_extinction_coef ? _refine_ls_number_reflns 2155 _refine_ls_number_parameters 150 _refine_ls_number_restraints 91 _refine_ls_R_factor_all 0.0615 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.000 _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 C33 C 1.553(2) 0.858(2) 0.953(3) 0.026(4) Uiso 0.25 1 d PU A -1 H33 H 1.6102 0.7492 0.9162 0.031 Uiso 0.25 1 calc PR A -1 C35 C 1.4501(17) 1.096(2) 0.953(2) 0.013(3) Uiso 0.25 1 d PU A -1 H35 H 1.4257 1.1893 0.9222 0.015 Uiso 0.25 1 calc PR A -1 C31 C 1.4846(19) 1.1167(16) 1.1076(17) 0.010(3) Uiso 0.25 1 d PU A -1 H31 H 1.4671 1.2199 1.2018 0.012 Uiso 0.25 1 calc PR A -1 N32 N 1.5472(13) 0.9692(19) 1.1077(15) 0.010(2) Uiso 0.25 1 d PU A -1 H32 H 1.5795 0.9485 1.1943 0.011 Uiso 0.25 1 calc PR A -1 N34 N 1.455(2) 0.934(2) 0.853(2) 0.025(4) Uiso 0.25 1 d PU A -1 H34 H 1.4070 0.8807 0.7451 0.030 Uiso 0.25 1 calc PR A -1 C43 C 1.531(2) 0.8370(16) 0.946(2) 0.014(3) Uiso 0.25 1 d PU B -2 H43 H 1.5452 0.7142 0.9134 0.017 Uiso 0.25 1 calc PR B -2 C44 C 1.457(2) 0.907(2) 0.845(2) 0.020(4) Uiso 0.25 1 d PU B -2 H44 H 1.4341 0.8498 0.7279 0.024 Uiso 0.25 1 calc PR B -2 C41 C 1.505(2) 1.133(2) 1.104(2) 0.024(4) Uiso 0.25 1 d PU B -2 H41 H 1.5171 1.2464 1.1982 0.029 Uiso 0.25 1 calc PR B -2 N42 N 1.5810(15) 0.973(2) 1.1026(16) 0.012(2) Uiso 0.25 1 d PU B -2 H42 H 1.6493 0.9651 1.1899 0.014 Uiso 0.25 1 calc PR B -2 N45 N 1.4162(14) 1.0916(19) 0.9521(18) 0.008(2) Uiso 0.25 1 d PU B -2 H45 H 1.3455 1.1597 0.9182 0.010 Uiso 0.25 1 calc PR B -2 C1 C 0.7674(2) 0.76677(19) 1.31734(17) 0.0160(3) Uani 1 1 d U . . C2 C 0.8881(2) 0.6933(2) 1.42492(18) 0.0195(3) Uani 1 1 d U . . H2A H 0.9947 0.7875 1.5092 0.023 Uiso 1 1 calc R . . H2B H 0.9499 0.5910 1.3548 0.023 Uiso 1 1 calc R . . C3 C 0.7635(2) 0.63102(19) 1.51257(17) 0.0186(3) Uani 1 1 d U . . C22 C 1.2685(2) 0.71211(19) 1.21213(18) 0.0185(3) Uani 1 1 d U . . H22 H 1.3462 0.6561 1.2688 0.022 Uiso 1 1 calc R . . C24 C 1.0995(2) 0.9070(2) 1.16006(18) 0.0209(3) Uani 1 1 d U . . H24 H 1.0393 1.0122 1.1758 0.025 Uiso 1 1 calc R . . C25 C 1.0938(2) 0.7632(2) 1.01332(18) 0.0203(3) Uani 1 1 d U . . H25 H 1.0287 0.7477 0.9063 0.024 Uiso 1 1 calc R . . N21 N 1.20075(18) 0.64320(16) 1.04885(15) 0.0185(3) Uani 1 1 d U . . H21 H 1.2209 0.5379 0.9751 0.022 Uiso 1 1 calc R . . N23 N 1.20903(19) 0.87278(16) 1.28277(15) 0.0186(3) Uani 1 1 d U . . H23 H 1.2353 0.9452 1.3901 0.022 Uiso 1 1 calc R . . O1A O 0.72204(16) 0.92378(14) 1.38826(12) 0.0217(3) Uani 1 1 d U . . O1B O 0.71556(16) 0.67146(14) 1.16262(12) 0.0225(3) Uani 1 1 d U . . O3A O 0.83446(17) 0.64742(15) 1.65192(13) 0.0269(3) Uani 1 1 d U . . O3B O 0.58687(17) 0.55875(16) 1.42739(14) 0.0288(3) Uani 1 1 d U . . H3B H 0.5000 0.5000 1.5000 0.092(13) Uiso 1 2 d S . . 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 0.0169(7) 0.0162(7) 0.0159(7) 0.0079(6) 0.0044(5) 0.0014(5) C2 0.0187(7) 0.0218(7) 0.0183(7) 0.0106(6) 0.0017(6) 0.0043(6) C3 0.0245(8) 0.0150(7) 0.0159(7) 0.0078(6) 0.0018(6) 0.0046(6) C22 0.0184(7) 0.0192(7) 0.0178(7) 0.0085(6) 0.0040(6) 0.0023(6) C24 0.0229(8) 0.0203(7) 0.0192(7) 0.0096(6) 0.0031(6) 0.0052(6) C25 0.0219(8) 0.0216(8) 0.0174(7) 0.0103(6) 0.0014(6) 0.0033(6) N21 0.0218(7) 0.0161(6) 0.0142(6) 0.0041(5) 0.0034(5) 0.0033(5) N23 0.0222(7) 0.0176(6) 0.0128(6) 0.0046(5) 0.0030(5) 0.0028(5) O1A 0.0296(6) 0.0169(5) 0.0160(5) 0.0055(4) 0.0043(4) 0.0061(4) O1B 0.0312(6) 0.0199(5) 0.0136(5) 0.0059(4) 0.0032(4) 0.0065(5) O3A 0.0317(7) 0.0316(6) 0.0155(5) 0.0123(5) -0.0015(5) 0.0006(5) O3B 0.0262(6) 0.0394(7) 0.0236(6) 0.0217(5) -0.0045(5) -0.0096(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C33 N32 1.33(2) . ? C33 N34 1.42(3) . ? C33 H33 0.9500 . ? C35 N34 1.26(3) . ? C35 C31 1.33(2) . ? C35 H35 0.9500 . ? C31 N32 1.320(19) . ? C31 H31 0.9500 . ? N32 H32 0.8800 . ? N34 H34 0.8800 . ? C43 C44 1.33(2) . ? C43 N42 1.35(2) . ? C43 H43 0.9500 . ? C44 N45 1.49(2) . ? C44 H44 0.9500 . ? C41 N45 1.30(2) . ? C41 N42 1.45(2) . ? C41 H41 0.9500 . ? N42 H42 0.8800 . ? N45 H45 0.8800 . ? C1 O1B 1.2571(17) . ? C1 O1A 1.2646(17) . ? C1 C2 1.5173(19) . ? C2 C3 1.528(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O3A 1.2267(17) . ? C3 O3B 1.2900(19) . ? C22 N21 1.3274(19) . ? C22 N23 1.3291(19) . ? C22 H22 0.9500 . ? C24 C25 1.350(2) . ? C24 N23 1.3781(19) . ? C24 H24 0.9500 . ? C25 N21 1.3787(19) . ? C25 H25 0.9500 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? O3B H3B 1.2294(11) . ? 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 N32 C33 N34 105.8(13) . . ? N32 C33 H33 127.1 . . ? N34 C33 H33 127.1 . . ? N34 C35 C31 109.9(10) . . ? N34 C35 H35 125.0 . . ? C31 C35 H35 125.0 . . ? N32 C31 C35 108.3(9) . . ? N32 C31 H31 125.8 . . ? C35 C31 H31 125.8 . . ? C31 N32 C33 107.4(10) . . ? C31 N32 H32 126.3 . . ? C33 N32 H32 126.3 . . ? C35 N34 C33 105.4(15) . . ? C35 N34 H34 127.3 . . ? C33 N34 H34 127.3 . . ? C44 C43 N42 107.5(12) . . ? C44 C43 H43 126.2 . . ? N42 C43 H43 126.2 . . ? C43 C44 N45 107.3(15) . . ? C43 C44 H44 126.4 . . ? N45 C44 H44 126.4 . . ? N45 C41 N42 106.9(10) . . ? N45 C41 H41 126.5 . . ? N42 C41 H41 126.5 . . ? C43 N42 C41 109.3(9) . . ? C43 N42 H42 125.4 . . ? C41 N42 H42 125.4 . . ? C41 N45 C44 107.1(11) . . ? C41 N45 H45 126.5 . . ? C44 N45 H45 126.5 . . ? O1B C1 O1A 122.22(13) . . ? O1B C1 C2 119.75(13) . . ? O1A C1 C2 118.03(12) . . ? C1 C2 C3 112.27(12) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? O3A C3 O3B 124.77(14) . . ? O3A C3 C2 120.26(14) . . ? O3B C3 C2 114.94(12) . . ? N21 C22 N23 108.38(13) . . ? N21 C22 H22 125.8 . . ? N23 C22 H22 125.8 . . ? C25 C24 N23 107.23(13) . . ? C25 C24 H24 126.4 . . ? N23 C24 H24 126.4 . . ? C24 C25 N21 106.70(13) . . ? C24 C25 H25 126.6 . . ? N21 C25 H25 126.6 . . ? C22 N21 C25 109.02(12) . . ? C22 N21 H21 125.5 . . ? C25 N21 H21 125.5 . . ? C22 N23 C24 108.67(12) . . ? C22 N23 H23 125.7 . . ? C24 N23 H23 125.7 . . ? C3 O3B H3B 111.50(10) . . ? 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 N32 H32 O1A 0.88 1.96 2.823(8) 164.8 1_655 N32 H32 O1B 0.88 2.45 2.978(11) 119.4 1_655 N42 H42 O1A 0.88 1.98 2.835(9) 162.4 1_655 N42 H42 O1B 0.88 2.42 2.949(12) 118.6 1_655 N21 H21 O1B 0.88 1.78 2.6611(16) 174.7 2_767 N23 H23 O1A 0.88 1.80 2.6771(16) 174.5 2_778 O3B H3B O3B 1.2294(11) 1.2294(11) 2.459(2) 180.000(1) 2_668 O3B H3B O3A 1.2294(11) 2.4447(11) 3.1626(16) 114.73(6) 2_668 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.277 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.055 #============================================================================== data_18 _database_code_depnum_ccdc_archive 'CCDC 745387' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Malonic Acid and 2-Methylimidazole ; _chemical_name_common 'Malonic Acid and 2-Methylimidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H10 N2 O4' _chemical_formula_weight 186.17 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna21 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' _cell_length_a 11.4966(19) _cell_length_b 18.702(3) _cell_length_c 3.9535(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 850.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1011 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9775 _exptl_absorpt_correction_T_max 0.9988 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5441 _diffrn_reflns_av_R_equivalents 0.0767 _diffrn_reflns_av_sigmaI/netI 0.0764 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 27.45 _reflns_number_total 1107 _reflns_number_gt 779 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^)+(0.0000P)^2^+1.8631P] 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_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 1107 _refine_ls_number_parameters 120 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1277 _refine_ls_R_factor_gt 0.0802 _refine_ls_wR_factor_ref 0.1429 _refine_ls_wR_factor_gt 0.1212 _refine_ls_goodness_of_fit_ref 1.163 _refine_ls_restrained_S_all 1.162 _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 C1 C 0.8672(5) 0.3500(3) 0.2787(17) 0.0282(15) Uani 1 1 d . . . C2 C 0.9050(5) 0.4163(3) 0.4731(16) 0.0248(14) Uani 1 1 d . . . H2A H 0.9476 0.4003 0.6771 0.030 Uiso 1 1 calc R . . H2B H 0.9610 0.4428 0.3302 0.030 Uiso 1 1 calc R . . C3 C 0.8118(5) 0.4681(3) 0.5851(17) 0.0278(15) Uani 1 1 d . . . O1A O 0.9400(4) 0.3043(2) 0.2071(13) 0.0342(11) Uani 1 1 d . . . O1B O 0.7594(4) 0.3457(2) 0.1963(14) 0.0373(12) Uani 1 1 d . . . H1 H 0.7244 0.3827 0.2605 0.056 Uiso 1 1 calc R . . O3A O 0.7068(3) 0.4551(2) 0.4830(12) 0.0324(11) Uani 1 1 d . . . O3B O 0.8383(4) 0.5200(2) 0.7600(14) 0.0379(12) Uani 1 1 d . . . C22 C 0.8060(5) 0.1602(3) -0.2860(19) 0.0268(14) Uani 1 1 d . . . C24 C 0.9478(5) 0.0869(3) -0.4337(17) 0.0304(15) Uani 1 1 d . . . H24 H 0.9884 0.0476 -0.5297 0.036 Uiso 1 1 calc R . . C25 C 0.9942(5) 0.1406(3) -0.2559(17) 0.0265(13) Uani 1 1 d . . . H25 H 1.0741 0.1464 -0.2011 0.032 Uiso 1 1 calc R . . C26 C 0.6900(5) 0.1916(3) -0.2388(19) 0.0355(17) Uani 1 1 d . . . H26A H 0.6978 0.2393 -0.1381 0.053 Uiso 1 1 calc R . . H26B H 0.6440 0.1610 -0.0885 0.053 Uiso 1 1 calc R . . H26C H 0.6510 0.1955 -0.4584 0.053 Uiso 1 1 calc R . . N21 N 0.9048(4) 0.1857(2) -0.1672(12) 0.0249(12) Uani 1 1 d . . . H21 H 0.9124 0.2253 -0.0496 0.030 Uiso 1 1 calc R . . N23 N 0.8299(4) 0.0994(2) -0.4512(14) 0.0267(12) Uani 1 1 d . . . H23 H 0.7788 0.0720 -0.5541 0.032 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 0.032(3) 0.025(3) 0.028(4) -0.005(3) 0.003(3) -0.007(2) C2 0.027(3) 0.022(3) 0.026(4) 0.001(3) 0.005(3) 0.000(2) C3 0.032(4) 0.021(3) 0.030(4) 0.005(3) 0.006(3) 0.003(3) O1A 0.034(2) 0.0237(19) 0.045(3) -0.007(2) 0.003(2) 0.0025(18) O1B 0.029(2) 0.026(2) 0.057(3) -0.013(3) -0.005(3) 0.0008(17) O3A 0.020(2) 0.032(2) 0.045(3) -0.006(2) 0.000(2) -0.0002(18) O3B 0.035(2) 0.029(2) 0.050(3) -0.018(2) -0.001(3) 0.0020(18) C22 0.029(3) 0.023(2) 0.029(4) 0.002(3) -0.001(3) -0.005(2) C24 0.036(4) 0.021(3) 0.034(4) -0.001(3) 0.004(3) 0.000(3) C25 0.023(3) 0.027(3) 0.029(4) 0.002(3) -0.002(3) 0.002(2) C26 0.034(4) 0.028(3) 0.045(5) 0.000(4) -0.004(4) 0.005(3) N21 0.025(3) 0.022(2) 0.028(3) -0.007(2) 0.000(2) -0.002(2) N23 0.028(3) 0.019(2) 0.033(3) -0.003(2) -0.004(2) -0.005(2) _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 O1A 1.229(7) . ? C1 O1B 1.284(7) . ? C1 C2 1.522(8) . ? C2 C3 1.512(8) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O3B 1.230(7) . ? C3 O3A 1.296(7) . ? O1B H1 0.8400 . ? C22 N21 1.319(7) . ? C22 N23 1.340(7) . ? C22 C26 1.469(8) . ? C24 C25 1.336(8) . ? C24 N23 1.376(8) . ? C24 H24 0.9500 . ? C25 N21 1.375(7) . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? 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 O1A C1 O1B 123.7(6) . . ? O1A C1 C2 119.2(5) . . ? O1B C1 C2 117.1(5) . . ? C3 C2 C1 117.9(5) . . ? C3 C2 H2A 107.8 . . ? C1 C2 H2A 107.8 . . ? C3 C2 H2B 107.8 . . ? C1 C2 H2B 107.8 . . ? H2A C2 H2B 107.2 . . ? O3B C3 O3A 123.6(5) . . ? O3B C3 C2 119.7(6) . . ? O3A C3 C2 116.7(5) . . ? C1 O1B H1 109.5 . . ? N21 C22 N23 107.6(5) . . ? N21 C22 C26 126.3(5) . . ? N23 C22 C26 126.0(5) . . ? C25 C24 N23 107.0(5) . . ? C25 C24 H24 126.5 . . ? N23 C24 H24 126.5 . . ? C24 C25 N21 107.2(5) . . ? C24 C25 H25 126.4 . . ? N21 C25 H25 126.4 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 N21 C25 109.4(5) . . ? C22 N21 H21 125.3 . . ? C25 N21 H21 125.3 . . ? C22 N23 C24 108.8(5) . . ? C22 N23 H23 125.6 . . ? C24 N23 H23 125.6 . . ? 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 O1B H1 O3A 0.84 1.63 2.417(6) 155.4 . N21 H21 O1A 0.88 1.82 2.698(6) 175.0 . N23 H23 O3B 0.88 1.82 2.692(6) 174.0 4_643 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.335 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.077 #============================================================================== data_19 _database_code_depnum_ccdc_archive 'CCDC 745388' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Maleic Acid & 4-Methylimidazole ; _chemical_name_common 'Maleic Acid & 4-Methylimidazole' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 N2 O4' _chemical_formula_weight 198.18 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_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.5883(2) _cell_length_b 22.5838(12) _cell_length_c 7.3581(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.578(3) _cell_angle_gamma 90.00 _cell_volume 918.24(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2048 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9549 _exptl_absorpt_correction_T_max 0.9839 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10396 _diffrn_reflns_av_R_equivalents 0.0623 _diffrn_reflns_av_sigmaI/netI 0.0576 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2102 _reflns_number_gt 1467 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^)+(0.0806P)^2^+0.0504P] 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 SHELXL _refine_ls_extinction_coef 0.034(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2102 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0854 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1248 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 C1 C -0.0335(3) 0.59343(8) 0.8364(3) 0.0221(4) Uani 1 1 d . . . C2 C -0.2414(3) 0.55630(8) 0.7509(3) 0.0242(4) Uani 1 1 d . . . H2 H -0.3935 0.5759 0.7319 0.029 Uiso 1 1 calc R . . C3 C -0.2461(3) 0.49960(8) 0.6971(3) 0.0232(4) Uani 1 1 d . . . H3 H -0.4022 0.4851 0.6487 0.028 Uiso 1 1 calc R . . C4 C -0.0467(3) 0.45520(8) 0.7003(3) 0.0231(4) Uani 1 1 d . . . O1A O 0.1792(2) 0.57073(6) 0.87320(18) 0.0272(4) Uani 1 1 d . . . O1B O -0.0743(2) 0.64605(6) 0.87330(18) 0.0271(4) Uani 1 1 d . . . O4A O 0.1716(2) 0.46934(6) 0.76915(19) 0.0289(4) Uani 1 1 d . . . H4 H 0.1753 0.5049 0.8031 0.043 Uiso 1 1 calc R . . O4B O -0.1001(2) 0.40549(6) 0.63697(19) 0.0300(4) Uani 1 1 d . . . C22 C 0.4765(3) 0.35864(8) 0.8538(3) 0.0233(4) Uani 1 1 d . . . H22 H 0.4931 0.3999 0.8767 0.028 Uiso 1 1 calc R . . C24 C 0.5503(3) 0.26232(8) 0.8574(3) 0.0235(4) Uani 1 1 d . . . C25 C 0.3311(3) 0.27224(8) 0.7540(3) 0.0249(4) Uani 1 1 d . . . H25 H 0.2256 0.2430 0.6936 0.030 Uiso 1 1 calc R . . C26 C 0.6886(4) 0.20680(9) 0.9047(3) 0.0301(5) Uani 1 1 d . . . H26A H 0.5987 0.1732 0.8443 0.045 Uiso 1 1 calc R . . H26B H 0.7117 0.2010 1.0382 0.045 Uiso 1 1 calc R . . H26C H 0.8468 0.2096 0.8630 0.045 Uiso 1 1 calc R . . N21 N 0.2898(3) 0.33271(7) 0.7530(2) 0.0242(4) Uani 1 1 d . . . H21 H 0.1612 0.3508 0.6951 0.029 Uiso 1 1 calc R . . N23 N 0.6366(3) 0.31758(7) 0.9176(2) 0.0231(4) Uani 1 1 d . . . H23 H 0.7760 0.3243 0.9874 0.028 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 0.0221(9) 0.0194(10) 0.0257(10) 0.0031(8) 0.0060(7) 0.0013(7) C2 0.0198(9) 0.0224(10) 0.0300(11) 0.0042(8) 0.0021(7) 0.0014(7) C3 0.0188(8) 0.0227(10) 0.0266(11) 0.0037(8) -0.0016(7) -0.0009(7) C4 0.0214(9) 0.0219(10) 0.0254(10) 0.0001(8) 0.0018(7) -0.0036(7) O1A 0.0184(6) 0.0221(7) 0.0396(8) -0.0042(6) -0.0006(5) 0.0006(5) O1B 0.0278(7) 0.0182(7) 0.0353(8) -0.0004(6) 0.0048(6) 0.0021(5) O4A 0.0207(6) 0.0173(7) 0.0472(9) -0.0078(6) -0.0004(5) 0.0007(5) O4B 0.0294(7) 0.0207(7) 0.0382(9) -0.0046(6) -0.0004(6) -0.0028(6) C22 0.0243(9) 0.0171(9) 0.0287(11) -0.0013(8) 0.0045(7) -0.0006(7) C24 0.0300(10) 0.0179(10) 0.0243(11) 0.0004(7) 0.0102(7) -0.0023(7) C25 0.0288(9) 0.0201(10) 0.0274(11) -0.0033(8) 0.0093(8) -0.0044(7) C26 0.0384(11) 0.0197(10) 0.0336(12) -0.0010(8) 0.0101(8) 0.0036(8) N21 0.0229(8) 0.0212(9) 0.0284(9) -0.0016(7) 0.0037(6) -0.0009(6) N23 0.0233(8) 0.0186(8) 0.0271(9) -0.0016(6) 0.0028(6) -0.0008(6) _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 O1B 1.247(2) . ? C1 O1A 1.285(2) . ? C1 C2 1.493(3) . ? C2 C3 1.340(3) . ? C2 H2 0.9500 . ? C3 C4 1.496(3) . ? C3 H3 0.9500 . ? C4 O4B 1.235(2) . ? C4 O4A 1.289(2) . ? O4A H4 0.8400 . ? C22 N21 1.323(2) . ? C22 N23 1.325(2) . ? C22 H22 0.9500 . ? C24 C25 1.360(3) . ? C24 N23 1.387(2) . ? C24 C26 1.487(3) . ? C25 N21 1.385(2) . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? 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 O1B C1 O1A 121.83(16) . . ? O1B C1 C2 118.07(15) . . ? O1A C1 C2 120.09(16) . . ? C3 C2 C1 129.86(17) . . ? C3 C2 H2 115.1 . . ? C1 C2 H2 115.1 . . ? C2 C3 C4 130.86(17) . . ? C2 C3 H3 114.6 . . ? C4 C3 H3 114.6 . . ? O4B C4 O4A 122.33(17) . . ? O4B C4 C3 117.75(16) . . ? O4A C4 C3 119.92(16) . . ? C4 O4A H4 109.5 . . ? N21 C22 N23 108.85(16) . . ? N21 C22 H22 125.6 . . ? N23 C22 H22 125.6 . . ? C25 C24 N23 105.77(16) . . ? C25 C24 C26 131.54(17) . . ? N23 C24 C26 122.69(16) . . ? C24 C25 N21 107.50(16) . . ? C24 C25 H25 126.3 . . ? N21 C25 H25 126.3 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 N21 C25 108.46(15) . . ? C22 N21 H21 125.8 . . ? C25 N21 H21 125.8 . . ? C22 N23 C24 109.41(16) . . ? C22 N23 H23 125.3 . . ? C24 N23 H23 125.3 . . ? 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 O4A H4 O1A 0.84 1.57 2.4127(18) 178.0 . N21 H21 O4B 0.88 1.91 2.761(2) 161.9 . N23 H23 O1B 0.88 1.94 2.811(2) 169.6 3_667 N23 H23 O1A 0.88 2.58 3.0526(19) 114.6 3_667 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.290 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.099