 
data_ssg0306
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
DL-Tartaric acid and 2-imidazolidinone
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C7 H12 N2 O7'
_chemical_formula_weight          236.19
 
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                    5.1062(11)
_cell_length_b                    18.198(4)
_cell_length_c                    10.432(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  97.060(2)
_cell_angle_gamma                 90.00
_cell_volume                      962.0(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     930
_cell_measurement_theta_min       3.94
_cell_measurement_theta_max       25.79
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.05
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.631
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              496
_exptl_absorpt_coefficient_mu     0.147
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    'Bruker SADABS'
# absolute Tmin and Tmax unknown, but SADABS gives ratio as 0.731
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.6710
_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 ω 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             7832
_diffrn_reflns_av_R_equivalents   0.0531
_diffrn_reflns_av_sigmaI/netI     0.0474
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -22
_diffrn_reflns_limit_k_max        22
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          2.81
_diffrn_reflns_theta_max          24.79
_reflns_number_total              1961
_reflns_number_gt                 1444
_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 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)+(0.0595P)²+0.0972P] 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      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          1961
_refine_ls_number_parameters      153
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0669
_refine_ls_R_factor_gt            0.0440
_refine_ls_wR_factor_ref          0.1189
_refine_ls_wR_factor_gt           0.1082
_refine_ls_goodness_of_fit_ref    1.101
_refine_ls_restrained_S_all       1.101
_refine_ls_shift/su_max           0.089
_refine_ls_shift/su_mean          0.004
 
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 0.6361(4) 0.56576(11) 0.1604(2) 0.0190(5) Uani 1 1 d . . .
C2 C 0.5051(4) 0.49326(11) 0.1877(2) 0.0199(5) Uani 1 1 d . . .
H2 H 0.6267 0.4528 0.1683 0.024 Uiso 1 1 calc R . .
C3 C 0.4862(4) 0.49157(11) 0.3337(2) 0.0210(5) Uani 1 1 d . . .
H3 H 0.6697 0.4908 0.3800 0.025 Uiso 1 1 calc R . .
C4 C 0.3463(4) 0.42249(12) 0.3705(2) 0.0206(5) Uani 1 1 d . . .
O1A O 0.8715(3) 0.57578(8) 0.19327(15) 0.0252(4) Uani 1 1 d . . .
O1B O 0.4758(3) 0.61498(8) 0.10313(15) 0.0235(4) Uani 1 1 d . . .
H1 H 0.5593 0.6540 0.0939 0.049(9) Uiso 1 1 calc R . .
O2 O 0.2592(3) 0.48121(8) 0.11205(14) 0.0229(4) Uani 1 1 d . . .
H2O H 0.1523 0.5141 0.1278 0.034 Uiso 1 1 calc R . .
O3 O 0.3586(3) 0.55494(8) 0.37336(14) 0.0224(4) Uani 1 1 d . . .
H3O H 0.1949 0.5506 0.3536 0.034 Uiso 1 1 calc R . .
O4A O 0.4812(3) 0.36240(8) 0.35348(15) 0.0233(4) Uani 1 1 d . . .
H4 H 0.3970 0.3256 0.3747 0.026(7) Uiso 1 1 calc R . .
O4B O 0.1318(3) 0.42435(8) 0.40880(15) 0.0251(4) Uani 1 1 d . . .
C22 C 0.1236(4) 0.23673(11) 0.5131(2) 0.0204(5) Uani 1 1 d . . .
C24 C -0.1703(4) 0.27755(12) 0.6500(2) 0.0239(5) Uani 1 1 d . . .
H24A H -0.3582 0.2921 0.6331 0.029 Uiso 1 1 calc R . .
H24B H -0.0869 0.3029 0.7286 0.029 Uiso 1 1 calc R . .
C25 C -0.1388(4) 0.19345(12) 0.6615(2) 0.0232(5) Uani 1 1 d . . .
H25A H -0.0980 0.1780 0.7527 0.028 Uiso 1 1 calc R . .
H25B H -0.2999 0.1677 0.6223 0.028 Uiso 1 1 calc R . .
N21 N 0.0843(4) 0.17954(11) 0.58870(18) 0.0251(4) Uani 1 1 d . . .
H21 H 0.1792 0.1391 0.5941 0.082(12) Uiso 1 1 calc R . .
N23 N -0.0298(4) 0.29246(10) 0.53864(19) 0.0263(5) Uani 1 1 d . . .
H23 H -0.0452 0.3335 0.4939 0.045(8) Uiso 1 1 calc R . .
O22 O 0.2864(3) 0.23811(8) 0.43046(15) 0.0233(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 0.0187(10) 0.0220(11) 0.0177(11) -0.0010(8) 0.0079(8) 0.0017(8)
C2 0.0165(10) 0.0223(11) 0.0213(12) -0.0003(8) 0.0047(8) 0.0002(8)
C3 0.0215(11) 0.0218(11) 0.0204(11) 0.0004(9) 0.0058(8) 0.0007(8)
C4 0.0213(10) 0.0237(11) 0.0176(11) 0.0001(9) 0.0049(8) 0.0009(9)
O1A 0.0196(8) 0.0267(8) 0.0298(9) 0.0014(7) 0.0057(6) -0.0013(6)
O1B 0.0217(8) 0.0222(8) 0.0274(9) 0.0043(7) 0.0063(6) 0.0001(6)
O2 0.0200(8) 0.0262(8) 0.0229(8) -0.0022(6) 0.0041(6) -0.0014(6)
O3 0.0222(7) 0.0237(8) 0.0224(8) -0.0020(6) 0.0067(6) 0.0005(6)
O4A 0.0244(8) 0.0210(8) 0.0265(9) 0.0018(7) 0.0106(6) -0.0006(6)
O4B 0.0214(8) 0.0252(8) 0.0306(9) 0.0025(7) 0.0103(6) 0.0006(6)
C22 0.0188(10) 0.0228(11) 0.0200(11) 0.0006(9) 0.0047(9) -0.0001(8)
C24 0.0230(11) 0.0270(12) 0.0233(12) 0.0003(9) 0.0087(9) 0.0001(9)
C25 0.0222(11) 0.0251(11) 0.0237(12) 0.0012(9) 0.0080(9) -0.0002(9)
N21 0.0253(9) 0.0249(10) 0.0274(11) 0.0047(8) 0.0131(8) 0.0025(8)
N23 0.0298(10) 0.0237(10) 0.0282(11) 0.0060(8) 0.0145(8) 0.0054(8)
O22 0.0237(8) 0.0233(8) 0.0244(8) 0.0006(6) 0.0096(6) -0.0003(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 1.222(2) . ?
C1 O1B 1.307(3) . ?
C1 C2 1.522(3) . ?
C2 O2 1.416(2) . ?
C2 C3 1.538(3) . ?
C2 H2 1.0000 . ?
C3 O3 1.411(2) . ?
C3 C4 1.518(3) . ?
C3 H3 1.0000 . ?
C4 O4B 1.212(3) . ?
C4 O4A 1.316(2) . ?
O1B H1 0.8400 . ?
O2 H2O 0.8400 . ?
O3 H3O 0.8400 . ?
O4A H4 0.8400 . ?
C22 O22 1.269(2) . ?
C22 N23 1.329(3) . ?
C22 N21 1.336(3) . ?
C24 N23 1.464(3) . ?
C24 C25 1.542(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.466(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
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 124.41(19) . . ?
O1A C1 C2 121.07(18) . . ?
O1B C1 C2 114.50(17) . . ?
O2 C2 C1 114.18(17) . . ?
O2 C2 C3 112.93(16) . . ?
C1 C2 C3 106.61(16) . . ?
O2 C2 H2 107.6 . . ?
C1 C2 H2 107.6 . . ?
C3 C2 H2 107.6 . . ?
O3 C3 C4 110.76(17) . . ?
O3 C3 C2 111.17(17) . . ?
C4 C3 C2 110.81(17) . . ?
O3 C3 H3 108.0 . . ?
C4 C3 H3 108.0 . . ?
C2 C3 H3 108.0 . . ?
O4B C4 O4A 125.25(19) . . ?
O4B C4 C3 122.18(19) . . ?
O4A C4 C3 112.55(17) . . ?
C1 O1B H1 109.5 . . ?
C2 O2 H2O 109.5 . . ?
C3 O3 H3O 109.5 . . ?
C4 O4A H4 109.5 . . ?
O22 C22 N23 124.96(19) . . ?
O22 C22 N21 125.10(19) . . ?
N23 C22 N21 109.93(18) . . ?
N23 C24 C25 100.88(17) . . ?
N23 C24 H24A 111.6 . . ?
C25 C24 H24A 111.6 . . ?
N23 C24 H24B 111.6 . . ?
C25 C24 H24B 111.6 . . ?
H24A C24 H24B 109.4 . . ?
N21 C25 C24 102.21(17) . . ?
N21 C25 H25A 111.3 . . ?
C24 C25 H25A 111.3 . . ?
N21 C25 H25B 111.3 . . ?
C24 C25 H25B 111.3 . . ?
H25A C25 H25B 109.2 . . ?
C22 N21 C25 110.73(18) . . ?
C22 N21 H21 124.6 . . ?
C25 N21 H21 124.6 . . ?
C22 N23 C24 112.11(18) . . ?
C22 N23 H23 123.9 . . ?
C24 N23 H23 123.9 . . ?
 
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
O4A H4 O22  0.84 1.81 2.636(2) 167.5 .
N23 H23 O4B  0.88 2.13 2.924(2) 150.0 .
O1B H1 O22  0.84 1.75 2.593(2) 176.1 2_655
O2 H2O O1A  0.84 2.01 2.831(2) 167.1 1_455
O3 H3O O1A  0.84 2.25 2.952(2) 141.4 1_455
N21 H21 O2  0.88 2.23 3.060(2) 157.1 4_566
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              24.79
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.365
_refine_diff_density_min   -0.253
_refine_diff_density_rms    0.064
