 
data_ssg0304
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
L-Tartaric Acid and 4-Methylimidazole
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C8 H12 N2 O6'
_chemical_formula_weight          232.20
 
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   0.0000
 '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    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                    7.5842(14)
_cell_length_b                    8.2124(16)
_cell_length_c                    32.363(6)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2015.7(7)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     978
_cell_measurement_theta_min       2.60
_cell_measurement_theta_max       24.76

_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.01
_exptl_crystal_size_mid           0.01
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.530
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              976
_exptl_absorpt_coefficient_mu     0.132
_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      0.6710
_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             16961
_diffrn_reflns_av_R_equivalents   0.0595
_diffrn_reflns_av_sigmaI/netI     0.0350
_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        -40
_diffrn_reflns_limit_l_max        40
_diffrn_reflns_theta_min          2.80
_diffrn_reflns_theta_max          24.80
_reflns_number_total              2392
_reflns_number_gt                 2175
_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)+(0.0465P)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     mixed
_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          2392
_refine_ls_number_parameters      303
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0372
_refine_ls_R_factor_gt            0.0316
_refine_ls_wR_factor_ref          0.0785
_refine_ls_wR_factor_gt           0.0756
_refine_ls_goodness_of_fit_ref    1.108
_refine_ls_restrained_S_all       1.108
_refine_ls_shift/su_max           0.030
_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 0.0607(3) 0.9964(3) 0.16838(7) 0.0173(5) Uani 1 1 d . . .
C2 C 0.2595(3) 1.0311(3) 0.16983(6) 0.0172(4) Uani 1 1 d . . .
H2 H 0.2783 1.1514 0.1678 0.021 Uiso 1 1 calc R . .
C3 C 0.3456(3) 0.9692(3) 0.20937(7) 0.0166(4) Uani 1 1 d . . .
H3 H 0.2798 1.0142 0.2336 0.020 Uiso 1 1 calc R . .
C4 C 0.5377(3) 1.0297(3) 0.21131(6) 0.0172(5) Uani 1 1 d . . .
O1A O -0.0195(2) 1.0301(2) 0.20304(5) 0.0253(4) Uani 1 1 d . . .
H1 H -0.1258 1.0019 0.2014 0.063(11) Uiso 1 1 calc R . .
O1B O -0.0110(2) 0.9466(2) 0.13744(5) 0.0253(4) Uani 1 1 d . . .
O2 O 0.3476(2) 0.9546(2) 0.13653(4) 0.0196(3) Uani 1 1 d . . .
H2O H 0.3049 0.9876 0.1141 0.029 Uiso 1 1 calc R . .
O3 O 0.3271(2) 0.79799(19) 0.20926(5) 0.0204(3) Uani 1 1 d . . .
H3O H 0.3570 0.7607 0.2324 0.031 Uiso 1 1 calc R . .
O4A O 0.6607(2) 0.9277(2) 0.20585(5) 0.0211(3) Uani 1 1 d . . .
O4B O 0.5572(2) 1.17717(19) 0.21850(5) 0.0227(4) Uani 1 1 d . . .
C22 C 0.2037(3) 0.6030(3) 0.10302(7) 0.0245(5) Uani 1 1 d . . .
H22 H 0.2588 0.6800 0.0853 0.029 Uiso 1 1 calc R . .
C24 C 0.1024(3) 0.4800(3) 0.15885(7) 0.0217(5) Uani 1 1 d . . .
C25 C 0.0580(3) 0.3896(3) 0.12555(7) 0.0235(5) Uani 1 1 d . . .
H25 H -0.0062 0.2903 0.1258 0.028 Uiso 1 1 calc R . .
C26 C 0.0672(4) 0.4559(4) 0.20372(7) 0.0350(6) Uani 1 1 d . . .
H26A H -0.0168 0.3664 0.2074 0.053 Uiso 1 1 calc R . .
H26B H 0.0176 0.5560 0.2154 0.053 Uiso 1 1 calc R . .
H26C H 0.1777 0.4294 0.2179 0.053 Uiso 1 1 calc R . .
N21 N 0.1228(3) 0.4677(3) 0.09126(6) 0.0246(5) Uani 1 1 d . . .
H21 H 0.1122 0.4335 0.0656 0.041(8) Uiso 1 1 calc R . .
N23 N 0.1940(3) 0.6117(2) 0.14386(6) 0.0227(4) Uani 1 1 d . . .
H23 H 0.2393 0.6900 0.1591 0.048(9) Uiso 1 1 calc R . .
C31 C 0.2469(3) 1.0060(3) 0.01852(6) 0.0166(4) Uani 1 1 d . . .
C32 C 0.0567(3) 1.0619(3) 0.02308(6) 0.0160(4) Uani 1 1 d . . .
H32 H 0.0348 1.1517 0.0029 0.019 Uiso 1 1 calc R . .
C33 C -0.0611(3) 0.9173(3) 0.01165(6) 0.0153(4) Uani 1 1 d . . .
H33 H -0.0356 0.8838 -0.0175 0.018 Uiso 1 1 calc R . .
C34 C -0.2525(3) 0.9738(3) 0.01473(6) 0.0152(4) Uani 1 1 d . . .
O31A O 0.33912(19) 0.9900(2) 0.05078(4) 0.0215(4) Uani 1 1 d . . .
O31B O 0.29795(19) 0.97397(19) -0.01741(4) 0.0186(3) Uani 1 1 d . . .
O32 O 0.0152(2) 1.1194(2) 0.06320(4) 0.0207(3) Uani 1 1 d . . .
H32O H 0.0111 1.0405 0.0797 0.031 Uiso 1 1 calc R . .
O33 O -0.0146(2) 0.78915(18) 0.03855(5) 0.0191(3) Uani 1 1 d . . .
H33O H -0.0589 0.7017 0.0300 0.029 Uiso 1 1 calc R . .
O34A O -0.3056(2) 1.08019(19) -0.00855(5) 0.0197(3) Uani 1 1 d . . .
O34B O -0.3457(2) 0.9018(2) 0.04315(5) 0.0208(3) Uani 1 1 d . . .
H34 H -0.4485 0.9400 0.0431 0.084(14) Uiso 1 1 calc R . .
C42 C -0.3123(3) 0.6923(3) 0.11954(7) 0.0210(5) Uani 1 1 d . . .
H42 H -0.2773 0.7971 0.1102 0.025 Uiso 1 1 calc R . .
C44 C -0.3779(3) 0.4295(3) 0.12054(7) 0.0206(5) Uani 1 1 d . . .
C45 C -0.3982(3) 0.4896(3) 0.15927(7) 0.0220(5) Uani 1 1 d . . .
H45 H -0.4343 0.4303 0.1830 0.026 Uiso 1 1 calc R . .
C46 C -0.4028(4) 0.2643(3) 0.10275(9) 0.0310(6) Uani 1 1 d . . .
H46A H -0.4103 0.1842 0.1251 0.047 Uiso 1 1 calc R . .
H46B H -0.3026 0.2377 0.0848 0.047 Uiso 1 1 calc R . .
H46C H -0.5119 0.2619 0.0865 0.047 Uiso 1 1 calc R . .
N41 N -0.3565(3) 0.6537(2) 0.15777(6) 0.0214(4) Uani 1 1 d . . .
H41 H -0.3591 0.7212 0.1789 0.050(10) Uiso 1 1 calc R . .
N43 N -0.3251(2) 0.5594(2) 0.09634(6) 0.0204(4) Uani 1 1 d . . .
H43 H -0.3034 0.5547 0.0697 0.034(8) Uiso 1 1 calc R . .
 
 
_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 1.210(3) . ?
C1 O1A 1.306(3) . ?
C1 C2 1.535(3) . ?
C2 O2 1.415(3) . ?
C2 C3 1.524(3) . ?
C2 H2 1.0000 . ?
C3 O3 1.413(3) . ?
C3 C4 1.541(3) . ?
C3 H3 1.0000 . ?
C4 O4B 1.242(3) . ?
C4 O4A 1.266(3) . ?
O1A H1 0.8400 . ?
O2 H2O 0.8400 . ?
O3 H3O 0.8400 . ?
C22 N23 1.326(3) . ?
C22 N21 1.325(3) . ?
C22 H22 0.9500 . ?
C24 C25 1.351(3) . ?
C24 N23 1.373(3) . ?
C24 C26 1.490(3) . ?
C25 N21 1.373(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 . ?
C31 O31B 1.253(3) . ?
C31 O31A 1.263(3) . ?
C31 C32 1.521(3) . ?
C32 O32 1.417(2) . ?
C32 C33 1.532(3) . ?
C32 H32 1.0000 . ?
C33 O33 1.410(3) . ?
C33 C34 1.527(3) . ?
C33 H33 1.0000 . ?
C34 O34A 1.222(3) . ?
C34 O34B 1.302(3) . ?
O32 H32O 0.8400 . ?
O33 H33O 0.8400 . ?
O34B H34 0.8400 . ?
C42 N41 1.321(3) . ?
C42 N43 1.329(3) . ?
C42 H42 0.9500 . ?
C44 C45 1.356(3) . ?
C44 N43 1.382(3) . ?
C44 C46 1.486(3) . ?
C45 N41 1.385(3) . ?
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
O1B C1 O1A 124.9(2) . . ?
O1B C1 C2 122.0(2) . . ?
O1A C1 C2 113.07(19) . . ?
O2 C2 C3 106.78(17) . . ?
O2 C2 C1 110.99(18) . . ?
C3 C2 C1 112.62(18) . . ?
O2 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
O3 C3 C2 106.70(18) . . ?
O3 C3 C4 114.49(18) . . ?
C2 C3 C4 109.39(17) . . ?
O3 C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C4 C3 H3 108.7 . . ?
O4B C4 O4A 125.7(2) . . ?
O4B C4 C3 115.8(2) . . ?
O4A C4 C3 118.54(19) . . ?
C1 O1A H1 109.5 . . ?
C2 O2 H2O 109.5 . . ?
C3 O3 H3O 109.5 . . ?
N23 C22 N21 107.8(2) . . ?
N23 C22 H22 126.1 . . ?
N21 C22 H22 126.1 . . ?
C25 C24 N23 106.1(2) . . ?
C25 C24 C26 131.3(2) . . ?
N23 C24 C26 122.7(2) . . ?
C24 C25 N21 107.4(2) . . ?
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 108.97(19) . . ?
C22 N21 H21 125.5 . . ?
C25 N21 H21 125.5 . . ?
C22 N23 C24 109.8(2) . . ?
C22 N23 H23 125.1 . . ?
C24 N23 H23 125.1 . . ?
O31B C31 O31A 125.0(2) . . ?
O31B C31 C32 116.50(18) . . ?
O31A C31 C32 118.43(18) . . ?
O32 C32 C31 113.59(17) . . ?
O32 C32 C33 110.49(17) . . ?
C31 C32 C33 107.18(18) . . ?
O32 C32 H32 108.5 . . ?
C31 C32 H32 108.5 . . ?
C33 C32 H32 108.5 . . ?
O33 C33 C34 115.09(18) . . ?
O33 C33 C32 106.48(17) . . ?
C34 C33 C32 107.62(17) . . ?
O33 C33 H33 109.2 . . ?
C34 C33 H33 109.2 . . ?
C32 C33 H33 109.2 . . ?
O34A C34 O34B 125.5(2) . . ?
O34A C34 C33 119.39(19) . . ?
O34B C34 C33 115.11(18) . . ?
C32 O32 H32O 109.5 . . ?
C33 O33 H33O 109.5 . . ?
C34 O34B H34 109.5 . . ?
N41 C42 N43 108.3(2) . . ?
N41 C42 H42 125.9 . . ?
N43 C42 H42 125.9 . . ?
C45 C44 N43 106.0(2) . . ?
C45 C44 C46 132.6(2) . . ?
N43 C44 C46 121.5(2) . . ?
C44 C45 N41 107.2(2) . . ?
C44 C45 H45 126.4 . . ?
N41 C45 H45 126.4 . . ?
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 108.9(2) . . ?
C42 N41 H41 125.5 . . ?
C45 N41 H41 125.5 . . ?
C42 N43 C44 109.58(18) . . ?
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
O2 H2O O31A  0.84 2.07 2.791(2) 144.4 .
N23 H23 O3  0.88 1.97 2.800(2) 157.5 .
N23 H23 O2  0.88 2.44 3.057(3) 128.1 .
O32 H32O O1B  0.84 2.03 2.797(2) 151.8 .
O1A H1 O4A  0.84 1.74 2.569(2) 170.4 1_455
O34B H34 O31A  0.84 1.68 2.510(2) 168.6 1_455
N41 H41 O4A  0.88 1.91 2.739(3) 155.7 1_455
N41 H41 O3  0.88 2.65 3.152(3) 117.2 1_455
O3 H3O O4B  0.84 1.85 2.687(2) 175.0 3_645
N21 H21 O34A  0.88 1.95 2.759(2) 151.9 4_565
O33 H33O O31B  0.84 1.85 2.676(2) 166.8 4_465
N43 H43 O31B  0.88 1.87 2.733(2) 165.6 4_465
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              24.80
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.256
_refine_diff_density_min   -0.187
_refine_diff_density_rms    0.047
