 
data_04skc0001c2c
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 DL-Tartaric Acid & imidazole
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_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    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                    25.065(5)
_cell_length_b                    4.9767(10)
_cell_length_c                    19.142(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  129.42(3)
_cell_angle_gamma                 90.00
_cell_volume                      1844.7(6)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     1871
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.09
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.571
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              912
_exptl_absorpt_coefficient_mu     0.139
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9876
_exptl_absorpt_correction_T_max   0.9917
_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 κ-goniostat'
_diffrn_measurement_method          'φ & ω 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             6173
_diffrn_reflns_av_R_equivalents   0.1934
_diffrn_reflns_av_sigmaI/netI     0.2636
_diffrn_reflns_limit_h_min        -32
_diffrn_reflns_limit_h_max        30
_diffrn_reflns_limit_k_min        -5
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_theta_min          4.21
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2017
_reflns_number_gt                 730
_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 F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0522P)²+0.0000P] where P=(Fo²+2Fc²)/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        0.0028(9)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2017
_refine_ls_number_parameters      163
_refine_ls_number_restraints      52
_refine_ls_R_factor_all           0.2794
_refine_ls_R_factor_gt            0.0993
_refine_ls_wR_factor_ref          0.1972
_refine_ls_wR_factor_gt           0.1418
_refine_ls_goodness_of_fit_ref    1.030
_refine_ls_restrained_S_all       1.017
_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 0.0749(3) -0.0634(11) 0.1412(4) 0.0311(14) Uani 1 1 d . . .
C2 C 0.1122(3) 0.0506(10) 0.2358(4) 0.0307(15) Uani 1 1 d . . .
H2 H 0.1016 -0.0687 0.2676 0.037 Uiso 1 1 calc R . .
C3 C 0.1902(3) 0.0409(11) 0.2886(4) 0.0318(15) Uani 1 1 d . . .
H3 H 0.2060 -0.1504 0.3026 0.038 Uiso 1 1 calc R . .
C4 C 0.2268(3) 0.1955(11) 0.3761(4) 0.0326(15) Uani 1 1 d . . .
O1A O 0.0324(2) 0.1006(7) 0.0766(2) 0.0358(11) Uani 1 1 d . . .
H1 H 0.0202 0.0389 0.0276 0.054 Uiso 0.50 1 calc PR . .
O1B O 0.08613(19) -0.2930(7) 0.1314(2) 0.0352(11) Uani 1 1 d . . .
O2 O 0.0908(2) 0.3151(7) 0.2358(3) 0.0362(11) Uani 1 1 d . . .
H2O H 0.0903 0.4112 0.1993 0.054 Uiso 1 1 calc R . .
O3 O 0.2069(2) 0.1557(7) 0.2363(3) 0.0371(11) Uani 1 1 d . . .
H3O H 0.2322 0.2909 0.2633 0.056 Uiso 1 1 calc R . .
O4A O 0.26037(19) 0.3956(7) 0.3889(2) 0.0385(11) Uani 1 1 d . . .
O4B O 0.2187(2) 0.0986(7) 0.4314(2) 0.0370(11) Uani 1 1 d . . .
H4 H 0.2467 0.1728 0.4821 0.055 Uiso 0.50 1 calc PR . .
C25B C 0.1054(8) 0.570(4) 0.4006(10) 0.030(3) Uani 0.519(11) 1 d PDU A 2
H25B H 0.1024 0.5541 0.3488 0.035 Uiso 0.519(11) 1 calc PR A 2
C24B C 0.0721(6) 0.426(3) 0.4195(12) 0.033(3) Uani 0.519(11) 1 d PDU A 2
H24B H 0.0405 0.2847 0.3832 0.039 Uiso 0.519(11) 1 calc PR A 2
N23B N 0.0904(6) 0.511(2) 0.4991(9) 0.034(4) Uani 0.519(11) 1 d PDU A 2
H23B H 0.0750 0.4449 0.5260 0.041 Uiso 0.519(11) 1 calc PR A 2
C22B C 0.1350(7) 0.709(3) 0.5300(9) 0.028(3) Uani 0.519(11) 1 d PDU A 2
H22B H 0.1561 0.8041 0.5848 0.034 Uiso 0.519(11) 1 calc PR A 2
N21B N 0.1456(9) 0.751(4) 0.4709(11) 0.030(3) Uani 0.519(11) 1 d PDU A 2
H21B H 0.1732 0.8727 0.4757 0.037 Uiso 0.519(11) 1 calc PR A 2
C25A C 0.1272(11) 0.618(5) 0.4151(13) 0.030(3) Uani 0.481(11) 1 d PD A 1
H25A H 0.1476 0.6514 0.3878 0.035 Uiso 0.481(11) 1 calc PR A 1
C24A C 0.0750(8) 0.454(3) 0.3854(11) 0.033(3) Uani 0.481(11) 1 d PD A 1
H24A H 0.0502 0.3516 0.3311 0.039 Uiso 0.481(11) 1 calc PR A 1
N23A N 0.0628(8) 0.456(3) 0.4451(12) 0.036(5) Uani 0.481(11) 1 d PD A 1
H23A H 0.0304 0.3645 0.4398 0.044 Uiso 0.481(11) 1 calc PR A 1
C22A C 0.1078(11) 0.616(3) 0.5117(12) 0.028(3) Uani 0.481(11) 1 d PD A 1
H22A H 0.1123 0.6470 0.5643 0.034 Uiso 0.481(11) 1 calc PR A 1
N21A N 0.1460(10) 0.730(4) 0.4942(13) 0.030(3) Uani 0.481(11) 1 d PD A 1
H21A H 0.1777 0.8539 0.5270 0.037 Uiso 0.481(11) 1 calc PR A 1
 
 
_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 1.219(6) . ?
C1 O1A 1.287(6) . ?
C1 C2 1.525(7) . ?
C2 O2 1.422(5) . ?
C2 C3 1.529(7) . ?
C2 H2 1.0000 . ?
C3 O3 1.426(6) . ?
C3 C4 1.513(8) . ?
C3 H3 1.0000 . ?
C4 O4A 1.225(6) . ?
C4 O4B 1.291(7) . ?
O1A H1 0.8400 . ?
O2 H2O 0.8400 . ?
O3 H3O 0.8400 . ?
O4B H4 0.8400 . ?
C25B C24B 1.314(15) . ?
C25B N21B 1.383(13) . ?
C25B H25B 0.9500 . ?
C24B N23B 1.352(16) . ?
C24B H24B 0.9500 . ?
N23B C22B 1.315(14) . ?
N23B H23B 0.8800 . ?
C22B N21B 1.331(14) . ?
C22B H22B 0.9500 . ?
N21B H21B 0.8800 . ?
C25A C24A 1.325(14) . ?
C25A N21A 1.386(14) . ?
C25A H25A 0.9500 . ?
C24A N23A 1.357(15) . ?
C24A H24A 0.9500 . ?
N23A C22A 1.309(16) . ?
N23A H23A 0.8800 . ?
C22A N21A 1.325(15) . ?
C22A H22A 0.9500 . ?
N21A H21A 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 125.3(5) . . ?
O1B C1 C2 120.2(5) . . ?
O1A C1 C2 114.4(5) . . ?
O2 C2 C1 113.4(4) . . ?
O2 C2 C3 110.7(4) . . ?
C1 C2 C3 109.6(5) . . ?
O2 C2 H2 107.6 . . ?
C1 C2 H2 107.6 . . ?
C3 C2 H2 107.6 . . ?
O3 C3 C4 109.4(4) . . ?
O3 C3 C2 110.2(5) . . ?
C4 C3 C2 109.7(5) . . ?
O3 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
O4A C4 O4B 125.9(5) . . ?
O4A C4 C3 119.4(6) . . ?
O4B C4 C3 114.7(5) . . ?
C1 O1A H1 109.5 . . ?
C2 O2 H2O 109.5 . . ?
C3 O3 H3O 109.5 . . ?
C4 O4B H4 109.5 . . ?
C24B C25B N21B 106.7(11) . . ?
C24B C25B H25B 126.6 . . ?
N21B C25B H25B 126.6 . . ?
C25B C24B N23B 108.4(11) . . ?
C25B C24B H24B 125.8 . . ?
N23B C24B H24B 125.8 . . ?
C22B N23B C24B 109.0(12) . . ?
C22B N23B H23B 125.5 . . ?
C24B N23B H23B 125.5 . . ?
N23B C22B N21B 108.0(13) . . ?
N23B C22B H22B 126.0 . . ?
N21B C22B H22B 126.0 . . ?
C22B N21B C25B 107.9(12) . . ?
C22B N21B H21B 126.1 . . ?
C25B N21B H21B 126.1 . . ?
C24A C25A N21A 105.9(13) . . ?
C24A C25A H25A 127.0 . . ?
N21A C25A H25A 127.0 . . ?
C25A C24A N23A 108.8(14) . . ?
C25A C24A H24A 125.6 . . ?
N23A C24A H24A 125.6 . . ?
C22A N23A C24A 108.1(13) . . ?
C22A N23A H23A 125.9 . . ?
C24A N23A H23A 125.9 . . ?
N23A C22A N21A 109.0(12) . . ?
N23A C22A H22A 125.5 . . ?
N21A C22A H22A 125.5 . . ?
C22A N21A C25A 107.9(12) . . ?
C22A N21A H21A 126.1 . . ?
C25A N21A H21A 126.1 . . ?
 
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
O3 H3O O4A  0.84 2.10 2.605(5) 118.5 .
O2 H2O O1B  0.84 1.92 2.741(5) 164.6 1_565
N21A H21A O4B  0.88 2.88 3.304(15) 111.7 1_565
O3 H3O O3  0.84 2.37 3.114(5) 148.2 4
O4B H4 O4B  0.84 1.72 2.528(7) 160.5 7_556
O4B H4 O4A  0.84 2.61 3.133(5) 121.9 7_556
N23B H23B O1B  0.88 2.00 2.819(13) 154.0 6_556
N21B H21B O4A  0.88 2.31 2.796(15) 114.8 7_566
N21A H21A O4A  0.88 1.84 2.706(16) 168.2 7_566
N23A H23A O1A  0.88 1.92 2.781(13) 167.3 2
O1A H1 O1A  0.84 1.69 2.490(7) 157.9 5
 
_diffrn_measured_fraction_theta_max    0.946
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.946
_refine_diff_density_max    0.288
_refine_diff_density_min   -0.344
_refine_diff_density_rms    0.073
