 
data_ssg0307
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
L-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            orthorhombic
_symmetry_space_group_name_H-M    P212121
 
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'
 
_cell_length_a                    5.3880(13)
_cell_length_b                    9.921(3)
_cell_length_c                    18.265(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      976.3(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     969
_cell_measurement_theta_min       2.26
_cell_measurement_theta_max       29.10
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.13
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.607
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              496
_exptl_absorpt_coefficient_mu     0.145
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   0.9309
_exptl_absorpt_correction_T_max   0.9913
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.6895
_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             8329
_diffrn_reflns_av_R_equivalents   0.0397
_diffrn_reflns_av_sigmaI/netI     0.0323
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -23
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          2.94
_diffrn_reflns_theta_max          26.59
_reflns_number_total              2167
_reflns_number_gt                 2085
_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)+(0.0464P)²+0.1957P] 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_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.8(9)
_refine_ls_number_reflns          2167
_refine_ls_number_parameters      153
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0322
_refine_ls_R_factor_gt            0.0311
_refine_ls_wR_factor_ref          0.0823
_refine_ls_wR_factor_gt           0.0814
_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 1.1160(3) 0.60658(15) -0.05338(7) 0.0174(3) Uani 1 1 d . . .
C2 C 1.1372(3) 0.52693(14) 0.01821(7) 0.0169(3) Uani 1 1 d . . .
H2 H 1.1058 0.5914 0.0593 0.020 Uiso 1 1 calc R . .
C3 C 1.4076(3) 0.48047(14) 0.02435(7) 0.0178(3) Uani 1 1 d . . .
H3 H 1.5195 0.5605 0.0287 0.021 Uiso 1 1 calc R . .
C4 C 1.4360(2) 0.39040(14) 0.09146(7) 0.0180(3) Uani 1 1 d . . .
O1A O 1.2386(2) 0.70662(11) -0.06445(6) 0.0238(2) Uani 1 1 d . . .
O1B O 0.9569(2) 0.55301(11) -0.10012(5) 0.0229(2) Uani 1 1 d . . .
H1 H 0.9595 0.5969 -0.1394 0.049(6) Uiso 1 1 calc R . .
O2 O 0.96735(19) 0.42004(10) 0.02578(5) 0.0190(2) Uani 1 1 d . . .
H2O H 1.0053 0.3578 -0.0033 0.028 Uiso 1 1 calc R . .
O3 O 1.46263(19) 0.40863(12) -0.04032(5) 0.0220(2) Uani 1 1 d . . .
H3O H 1.6171 0.4058 -0.0463 0.033 Uiso 1 1 calc R . .
O4A O 1.4161(2) 0.45960(10) 0.15306(5) 0.0228(2) Uani 1 1 d . . .
H4 H 1.4477 0.4090 0.1887 0.035(5) Uiso 1 1 calc R . .
O4B O 1.4730(2) 0.27023(10) 0.08849(5) 0.0221(2) Uani 1 1 d . . .
C22 C 0.7534(3) 0.24973(14) 0.26381(7) 0.0187(3) Uani 1 1 d . . .
C24 C 1.0941(3) 0.11554(15) 0.29045(8) 0.0231(3) Uani 1 1 d . . .
H24A H 1.0601 0.0342 0.3202 0.028 Uiso 1 1 calc R . .
H24B H 1.2722 0.1390 0.2945 0.028 Uiso 1 1 calc R . .
C25 C 1.0167(3) 0.09513(18) 0.21033(9) 0.0317(4) Uani 1 1 d . . .
H25A H 1.1396 0.1350 0.1763 0.038 Uiso 1 1 calc R . .
H25B H 0.9959 -0.0017 0.1987 0.038 Uiso 1 1 calc R . .
N21 N 0.7804(3) 0.16654(14) 0.20690(7) 0.0252(3) Uani 1 1 d . . .
H21 H 0.6699 0.1561 0.1719 0.068(8) Uiso 1 1 calc R . .
N23 N 0.9358(3) 0.22821(13) 0.31230(7) 0.0245(3) Uani 1 1 d . . .
H23 H 0.9576 0.2760 0.3524 0.038(5) Uiso 1 1 calc R . .
O22 O 0.58214(19) 0.33569(11) 0.27097(5) 0.0222(2) 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 0.0141(6) 0.0219(6) 0.0162(6) 0.0005(5) 0.0019(5) 0.0040(6)
C2 0.0146(6) 0.0208(6) 0.0154(6) -0.0001(5) -0.0004(5) 0.0004(5)
C3 0.0150(7) 0.0219(6) 0.0166(6) 0.0000(5) -0.0011(5) -0.0003(5)
C4 0.0122(6) 0.0241(6) 0.0177(6) 0.0002(5) -0.0020(5) -0.0008(6)
O1A 0.0243(6) 0.0246(5) 0.0224(5) 0.0047(4) 0.0003(4) -0.0024(4)
O1B 0.0244(5) 0.0280(5) 0.0164(5) 0.0037(4) -0.0051(4) -0.0020(4)
O2 0.0157(5) 0.0204(5) 0.0207(5) -0.0001(4) 0.0011(4) -0.0012(4)
O3 0.0145(5) 0.0337(5) 0.0179(5) -0.0012(4) 0.0023(4) 0.0043(5)
O4A 0.0272(6) 0.0242(5) 0.0171(5) -0.0010(4) -0.0057(4) 0.0042(5)
O4B 0.0233(5) 0.0227(5) 0.0205(5) -0.0001(4) -0.0035(4) 0.0040(4)
C22 0.0192(7) 0.0211(6) 0.0158(6) 0.0024(5) 0.0006(5) -0.0018(6)
C24 0.0187(7) 0.0274(7) 0.0232(7) 0.0016(6) -0.0026(6) 0.0031(6)
C25 0.0329(9) 0.0380(8) 0.0243(7) -0.0054(6) -0.0054(6) 0.0168(8)
N21 0.0258(7) 0.0305(6) 0.0193(6) -0.0054(5) -0.0054(5) 0.0089(6)
N23 0.0268(7) 0.0264(6) 0.0203(6) -0.0037(5) -0.0066(5) 0.0042(5)
O22 0.0225(5) 0.0277(5) 0.0165(4) -0.0010(4) -0.0005(4) 0.0055(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
C1 O1A 1.2091(18) . ?
C1 O1B 1.3215(17) . ?
C1 C2 1.5321(19) . ?
C2 O2 1.4073(17) . ?
C2 C3 1.5324(19) . ?
C2 H2 1.0000 . ?
C3 O3 1.4110(17) . ?
C3 C4 1.5246(19) . ?
C3 H3 1.0000 . ?
C4 O4B 1.2100(18) . ?
C4 O4A 1.3224(17) . ?
O1B H1 0.8400 . ?
O2 H2O 0.8400 . ?
O3 H3O 0.8400 . ?
O4A H4 0.8400 . ?
C22 O22 1.2634(18) . ?
C22 N21 1.3352(19) . ?
C22 N23 1.3401(18) . ?
C24 N23 1.461(2) . ?
C24 C25 1.535(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N21 1.458(2) . ?
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 125.20(13) . . ?
O1A C1 C2 121.70(13) . . ?
O1B C1 C2 113.08(12) . . ?
O2 C2 C1 115.10(11) . . ?
O2 C2 C3 112.60(12) . . ?
C1 C2 C3 106.75(11) . . ?
O2 C2 H2 107.3 . . ?
C1 C2 H2 107.3 . . ?
C3 C2 H2 107.3 . . ?
O3 C3 C4 110.85(12) . . ?
O3 C3 C2 106.89(11) . . ?
C4 C3 C2 109.31(11) . . ?
O3 C3 H3 109.9 . . ?
C4 C3 H3 109.9 . . ?
C2 C3 H3 109.9 . . ?
O4B C4 O4A 124.26(13) . . ?
O4B C4 C3 123.92(13) . . ?
O4A C4 C3 111.82(12) . . ?
C1 O1B H1 109.5 . . ?
C2 O2 H2O 109.5 . . ?
C3 O3 H3O 109.5 . . ?
C4 O4A H4 109.5 . . ?
O22 C22 N21 125.27(13) . . ?
O22 C22 N23 125.09(13) . . ?
N21 C22 N23 109.64(13) . . ?
N23 C24 C25 101.69(12) . . ?
N23 C24 H24A 111.4 . . ?
C25 C24 H24A 111.4 . . ?
N23 C24 H24B 111.4 . . ?
C25 C24 H24B 111.4 . . ?
H24A C24 H24B 109.3 . . ?
N21 C25 C24 102.36(12) . . ?
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 111.22(12) . . ?
C22 N21 H21 124.4 . . ?
C25 N21 H21 124.4 . . ?
C22 N23 C24 111.68(12) . . ?
C22 N23 H23 124.2 . . ?
C24 N23 H23 124.2 . . ?
 
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
O1B H1 O22  0.84 1.78 2.6090(15) 167.9 2_664
O2 H2O O4B  0.84 2.02 2.8144(15) 158.5 4_455
O3 H3O O2  0.84 2.30 2.9775(16) 137.4 1_655
O3 H3O O1B  0.84 2.54 3.2151(16) 138.2 1_655
O4A H4 O22  0.84 1.82 2.6362(15) 163.7 1_655
N21 H21 O4B  0.88 2.17 2.9119(16) 141.1 1_455
N23 H23 O1A  0.88 2.24 2.9261(18) 134.7 2_765
 
_diffrn_measured_fraction_theta_max    0.977
_diffrn_reflns_theta_full              26.59
_diffrn_measured_fraction_theta_full   0.977
_refine_diff_density_max    0.330
_refine_diff_density_min   -0.176
_refine_diff_density_rms    0.041
