# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_IMLT _database_code_depnum_ccdc_archive 'CCDC 918617' #TrackingRef '16708_web_deposit_cif_file_0_ChengminJi_1357697415.Imidazolium L-Tartrate .cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_absolute_configuration unk _chemical_name_common 'Imidazolium L-Tartrate' _chemical_melting_point ? _chemical_formula_moiety C7H10N2O6 _chemical_formula_sum 'C7 H10 N2 O6' _chemical_formula_weight 218.17 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 P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.577(3) _cell_length_b 6.894(2) _cell_length_c 8.927(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.174(5) _cell_angle_gamma 90.00 _cell_volume 455.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1482 _cell_measurement_theta_min 2.3339 _cell_measurement_theta_max 27.4855 _exptl_crystal_description BLOCK _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 228 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.967 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 120 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5245 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _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 2.33 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2019 _reflns_number_gt 1957 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0386P)^2^+0.0596P] 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 2019 _refine_ls_number_parameters 144 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0257 _refine_ls_R_factor_gt 0.0246 _refine_ls_wR_factor_ref 0.0641 _refine_ls_wR_factor_gt 0.0635 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.84438(11) 0.38253(14) 0.76027(9) 0.01443(19) Uani 1 1 d . . . N1 N 0.89626(13) 0.29480(17) 1.31814(11) 0.0153(2) Uani 1 1 d . . . H1A H 0.8466 0.2816 1.3982 0.018 Uiso 1 1 calc R . . C1 C 1.06660(16) 0.3669(2) 1.32119(13) 0.0159(2) Uani 1 1 d . . . H1B H 1.1507 0.4112 1.4089 0.019 Uiso 1 1 calc R . . H6 H 0.013(3) 0.346(4) 0.709(3) 0.057(6) Uiso 1 1 d . . . O2 O 0.69342(11) 0.26321(13) 0.53525(9) 0.0165(2) Uani 1 1 d . . . N2 N 0.93557(15) 0.28745(17) 1.08689(11) 0.0160(2) Uani 1 1 d . . . H2A H 0.9162 0.2682 0.9873 0.019 Uiso 1 1 calc R . . C2 C 1.09119(16) 0.3627(2) 1.17554(13) 0.0158(2) Uani 1 1 d . . . H2B H 1.1956 0.4037 1.1411 0.019 Uiso 1 1 calc R . . O3 O 0.54525(12) 0.49868(14) 0.84377(10) 0.0169(2) Uani 1 1 d . . . C3 C 0.81931(17) 0.24854(19) 1.17505(14) 0.0164(3) Uani 1 1 d . . . H3B H 0.7015 0.1966 1.1415 0.020 Uiso 1 1 calc R . . O4 O 0.54471(12) 0.08248(15) 0.85399(10) 0.0188(2) Uani 1 1 d . . . H4A H 0.4970 0.0734 0.9305 0.028 Uiso 1 1 calc R . . C4 C 0.70166(15) 0.33801(17) 0.66320(12) 0.0118(2) Uani 1 1 d . . . O5 O 0.22583(11) 0.19316(13) 0.90922(9) 0.01569(19) Uani 1 1 d . . . C5 C 0.52286(15) 0.38168(18) 0.71017(12) 0.0118(2) Uani 1 1 d . . . H5A H 0.4424 0.4520 0.6240 0.014 Uiso 1 1 calc R . . O6 O 0.13453(11) 0.32103(14) 0.67478(9) 0.0154(2) Uani 1 1 d . . . C6 C 0.43062(15) 0.19097(17) 0.73805(13) 0.0126(2) Uani 1 1 d . . . H6A H 0.4064 0.1136 0.6411 0.015 Uiso 1 1 calc R . . C7 C 0.25141(15) 0.23525(18) 0.78319(13) 0.0121(2) Uani 1 1 d . . . H3A H 0.655(3) 0.530(3) 0.869(2) 0.033(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0092(4) 0.0207(5) 0.0134(4) -0.0008(3) 0.0024(3) -0.0005(3) N1 0.0173(5) 0.0172(5) 0.0132(4) 0.0007(4) 0.0072(4) -0.0007(4) C1 0.0152(5) 0.0170(6) 0.0146(5) -0.0006(5) 0.0015(4) -0.0015(5) O2 0.0133(4) 0.0250(5) 0.0125(4) -0.0027(3) 0.0054(3) -0.0010(4) N2 0.0190(5) 0.0170(5) 0.0119(4) -0.0021(4) 0.0035(4) -0.0013(4) C2 0.0154(5) 0.0159(6) 0.0178(6) -0.0003(5) 0.0073(4) -0.0014(5) O3 0.0106(4) 0.0225(5) 0.0184(4) -0.0083(4) 0.0049(3) -0.0031(4) C3 0.0149(5) 0.0167(6) 0.0175(6) 0.0006(5) 0.0035(4) -0.0020(5) O4 0.0145(5) 0.0242(5) 0.0192(4) 0.0095(4) 0.0066(3) 0.0073(4) C4 0.0097(5) 0.0137(6) 0.0126(5) 0.0029(4) 0.0036(4) 0.0002(4) O5 0.0129(4) 0.0221(5) 0.0129(4) 0.0028(3) 0.0045(3) 0.0020(4) C5 0.0092(5) 0.0154(5) 0.0109(5) -0.0008(4) 0.0025(4) 0.0007(4) O6 0.0094(4) 0.0237(5) 0.0135(4) 0.0027(4) 0.0034(3) 0.0016(4) C6 0.0113(5) 0.0143(6) 0.0124(5) 0.0006(4) 0.0026(4) 0.0016(4) C7 0.0108(5) 0.0127(6) 0.0130(5) -0.0019(4) 0.0030(4) -0.0014(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.2726(14) . ? N1 C3 1.3265(17) . ? N1 C1 1.3782(17) . ? N1 H1A 0.8800 . ? C1 C2 1.3523(17) . ? C1 H1B 0.9500 . ? O2 C4 1.2428(15) . ? N2 C3 1.3266(16) . ? N2 C2 1.3756(17) . ? N2 H2A 0.8800 . ? C2 H2B 0.9500 . ? O3 C5 1.4202(14) . ? O3 H3A 0.840(19) . ? C3 H3B 0.9500 . ? O4 C6 1.4145(14) . ? O4 H4A 0.8400 . ? C4 C5 1.5302(16) . ? O5 C7 1.2164(15) . ? C5 C6 1.5339(17) . ? C5 H5A 1.0000 . ? O6 C7 1.3074(15) . ? O6 H6 1.04(2) . ? C6 C7 1.5265(16) . ? C6 H6A 1.0000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 C1 108.99(10) . . ? C3 N1 H1A 125.5 . . ? C1 N1 H1A 125.5 . . ? C2 C1 N1 106.95(11) . . ? C2 C1 H1B 126.5 . . ? N1 C1 H1B 126.5 . . ? C3 N2 C2 109.32(10) . . ? C3 N2 H2A 125.3 . . ? C2 N2 H2A 125.3 . . ? C1 C2 N2 106.63(11) . . ? C1 C2 H2B 126.7 . . ? N2 C2 H2B 126.7 . . ? C5 O3 H3A 107.9(13) . . ? N2 C3 N1 108.10(11) . . ? N2 C3 H3B 125.9 . . ? N1 C3 H3B 125.9 . . ? C6 O4 H4A 109.5 . . ? O2 C4 O1 126.63(10) . . ? O2 C4 C5 117.24(10) . . ? O1 C4 C5 116.13(10) . . ? O3 C5 C4 112.71(9) . . ? O3 C5 C6 109.17(9) . . ? C4 C5 C6 109.62(10) . . ? O3 C5 H5A 108.4 . . ? C4 C5 H5A 108.4 . . ? C6 C5 H5A 108.4 . . ? C7 O6 H6 111.2(13) . . ? O4 C6 C7 110.67(10) . . ? O4 C6 C5 110.06(10) . . ? C7 C6 C5 109.42(10) . . ? O4 C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6A 108.9 . . ? O5 C7 O6 125.27(11) . . ? O5 C7 C6 121.37(10) . . ? O6 C7 C6 113.36(10) . . ? 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 C3 N1 C1 C2 -0.16(16) . . . . ? N1 C1 C2 N2 -0.20(15) . . . . ? C3 N2 C2 C1 0.49(16) . . . . ? C2 N2 C3 N1 -0.60(16) . . . . ? C1 N1 C3 N2 0.47(16) . . . . ? O2 C4 C5 O3 -168.92(10) . . . . ? O1 C4 C5 O3 11.09(15) . . . . ? O2 C4 C5 C6 69.26(13) . . . . ? O1 C4 C5 C6 -110.72(12) . . . . ? O3 C5 C6 O4 -65.12(12) . . . . ? C4 C5 C6 O4 58.78(12) . . . . ? O3 C5 C6 C7 56.69(12) . . . . ? C4 C5 C6 C7 -179.40(9) . . . . ? O4 C6 C7 O5 5.81(16) . . . . ? C5 C6 C7 O5 -115.64(12) . . . . ? O4 C6 C7 O6 -174.51(10) . . . . ? C5 C6 C7 O6 64.04(13) . . . . ? 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 N1 H1A O2 0.88 1.86 2.7245(15) 167.1 1_556 O6 H6 O1 1.04(2) 1.47(2) 2.5107(14) 179(2) 1_455 O6 H6 O2 1.04(2) 2.65(2) 3.3357(16) 123.2(16) 1_455 O4 H4A O3 0.84 2.17 2.9756(15) 161.3 2_647 O3 H3A O5 0.840(19) 2.291(19) 2.8384(14) 123.1(15) 2_657 N2 H2A O1 0.88 2.14 2.9257(17) 149.1 . O4 H4A O5 0.84 2.19 2.6770(15) 117.3 . O3 H3A O1 0.840(19) 2.151(18) 2.6547(14) 118.3(16) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.224 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.057