 
data_04mbh0608
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
DL-Tartaric acid & TEMED trihydrate
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C10 H28 N2 O9'
_chemical_formula_weight          320.34
 
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'
 'O'  'O'   0.0106   0.0060
 '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'
 
_symmetry_cell_setting            Triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    6.1179(14)
_cell_length_b                    8.672(2)
_cell_length_c                    15.182(8)
_cell_angle_alpha                 90.92(3)
_cell_angle_beta                  91.41(3)
_cell_angle_gamma                 99.79(2)
_cell_volume                      793.3(5)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3376
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        lath
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.70
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.341
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              348
_exptl_absorpt_coefficient_mu     0.117
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9226
_exptl_absorpt_correction_T_max   0.9884
_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             12962
_diffrn_reflns_av_R_equivalents   0.0349
_diffrn_reflns_av_sigmaI/netI     0.0366
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          3.38
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3575
_reflns_number_gt                 2759
_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)+(0.0479P)²+0.3813P] 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_number_reflns          3575
_refine_ls_number_parameters      222
_refine_ls_number_restraints      9
_refine_ls_R_factor_all           0.0635
_refine_ls_R_factor_gt            0.0436
_refine_ls_wR_factor_ref          0.1122
_refine_ls_wR_factor_gt           0.1017
_refine_ls_goodness_of_fit_ref    1.032
_refine_ls_restrained_S_all       1.031
_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 0.6475(3) 0.01911(19) 0.65416(13) 0.0276(4) Uani 1 1 d . . .
C2 C 0.5684(2) 0.17622(17) 0.66138(10) 0.0182(3) Uani 1 1 d . . .
H2 H 0.6930 0.2555 0.6867 0.022 Uiso 1 1 calc R . .
C3 C 0.3745(2) 0.16292(17) 0.72369(10) 0.0175(3) Uani 1 1 d . . .
H3 H 0.4277 0.1348 0.7832 0.021 Uiso 1 1 calc R . .
C4 C 0.2891(2) 0.31759(17) 0.73268(10) 0.0164(3) Uani 1 1 d . . .
O1A O 0.6183(2) -0.05369(15) 0.58239(10) 0.0453(4) Uani 1 1 d . . .
O1B O 0.7404(2) -0.02814(14) 0.72103(10) 0.0375(3) Uani 1 1 d . . .
O2 O 0.50667(19) 0.22713(13) 0.57785(7) 0.0237(3) Uani 1 1 d . . .
H2O H 0.4874 0.1512 0.5418 0.036 Uiso 1 1 calc R . .
O3 O 0.20519(17) 0.04155(12) 0.69337(8) 0.0237(3) Uani 1 1 d . . .
H3O H 0.0813 0.0694 0.6992 0.036 Uiso 1 1 calc R . .
O4A O 0.09570(17) 0.32223(13) 0.71051(8) 0.0250(3) Uani 1 1 d . . .
O4B O 0.42712(17) 0.43286(12) 0.76616(7) 0.0193(2) Uani 1 1 d . . .
C21 C 0.0144(3) 0.7844(2) 0.52302(11) 0.0278(4) Uani 1 1 d . . .
H21A H 0.0871 0.7029 0.4970 0.042 Uiso 1 1 calc R . .
H21B H 0.1247 0.8788 0.5351 0.042 Uiso 1 1 calc R . .
H21C H -0.1002 0.8087 0.4818 0.042 Uiso 1 1 calc R . .
C23 C 0.0835(2) 0.68586(17) 0.66857(10) 0.0178(3) Uani 1 1 d . . .
H23A H 0.2132 0.7715 0.6712 0.021 Uiso 1 1 calc R . .
H23B H 0.1335 0.5900 0.6464 0.021 Uiso 1 1 calc R . .
C24 C -0.0057(2) 0.65822(18) 0.75996(10) 0.0200(3) Uani 1 1 d . . .
H24A H -0.0693 0.7500 0.7800 0.024 Uiso 1 1 calc R . .
H24B H -0.1253 0.5656 0.7586 0.024 Uiso 1 1 calc R . .
C26 C 0.0796(3) 0.5505(2) 0.90180(11) 0.0272(4) Uani 1 1 d . . .
H26A H 0.1995 0.5392 0.9440 0.041 Uiso 1 1 calc R . .
H26B H -0.0015 0.4467 0.8843 0.041 Uiso 1 1 calc R . .
H26C H -0.0221 0.6116 0.9293 0.041 Uiso 1 1 calc R . .
C27 C -0.2768(3) 0.5962(2) 0.59038(12) 0.0290(4) Uani 1 1 d . . .
H27A H -0.2192 0.5039 0.5693 0.044 Uiso 1 1 calc R . .
H27B H -0.3795 0.6262 0.5458 0.044 Uiso 1 1 calc R . .
H27C H -0.3551 0.5718 0.6453 0.044 Uiso 1 1 calc R . .
C28 C 0.3272(3) 0.77909(19) 0.84870(12) 0.0277(4) Uani 1 1 d . . .
H28A H 0.3924 0.8296 0.7959 0.041 Uiso 1 1 calc R . .
H28B H 0.4456 0.7546 0.8880 0.041 Uiso 1 1 calc R . .
H28C H 0.2441 0.8499 0.8793 0.041 Uiso 1 1 calc R . .
N22 N -0.0893(2) 0.72791(14) 0.60667(9) 0.0190(3) Uani 1 1 d . . .
H22 H -0.1463 0.8102 0.6324 0.037(5) Uiso 1 1 calc R . .
N25 N 0.1750(2) 0.63227(14) 0.82267(8) 0.0180(3) Uani 1 1 d . . .
H25 H 0.2585 0.5669 0.7946 0.032(5) Uiso 1 1 calc R . .
O1W O 0.8204(2) 0.08376(18) 0.89158(10) 0.0403(4) Uani 1 1 d D . .
H1W H 0.785(5) 0.054(4) 0.8372(13) 0.096(12) Uiso 1 1 d D . .
H2W H 0.743(4) 0.154(3) 0.9012(18) 0.077(10) Uiso 1 1 d D . .
O2W O 0.5882(2) 0.32312(16) 0.92446(9) 0.0341(3) Uani 1 1 d D . .
H21W H 0.465(3) 0.280(3) 0.9449(15) 0.067(8) Uiso 1 1 d D . .
H22W H 0.551(4) 0.363(3) 0.8762(12) 0.051(7) Uiso 1 1 d D . .
O3W O -0.2057(2) 0.82965(17) 1.00407(10) 0.0395(3) Uani 1 1 d D . .
H31W H -0.203(4) 0.910(2) 0.9723(14) 0.064(8) Uiso 1 1 d D . .
H32W H -0.095(4) 0.856(3) 1.0406(14) 0.063(8) Uiso 1 1 d D . .
 
 
_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 1.244(2) . ?
C1 O1B 1.259(2) . ?
C1 C2 1.525(2) . ?
C2 O2 1.413(2) . ?
C2 C3 1.525(2) . ?
C2 H2 1.0000 . ?
C3 O3 1.4082(18) . ?
C3 C4 1.526(2) . ?
C3 H3 1.0000 . ?
C4 O4A 1.2293(18) . ?
C4 O4B 1.2831(18) . ?
O2 H2O 0.8400 . ?
O3 H3O 0.8400 . ?
C21 N22 1.486(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C23 N22 1.4924(19) . ?
C23 C24 1.511(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 N25 1.490(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C26 N25 1.486(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 N22 1.487(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 N25 1.485(2) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N22 H22 0.9300 . ?
N25 H25 0.9300 . ?
O1W H1W 0.871(17) . ?
O1W H2W 0.845(16) . ?
O2W H21W 0.850(16) . ?
O2W H22W 0.855(16) . ?
O3W H31W 0.854(16) . ?
O3W H32W 0.863(16) . ?
 
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 124.07(16) . . ?
O1A C1 C2 118.02(17) . . ?
O1B C1 C2 117.90(16) . . ?
O2 C2 C1 111.28(13) . . ?
O2 C2 C3 110.59(12) . . ?
C1 C2 C3 109.59(12) . . ?
O2 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
O3 C3 C2 109.24(12) . . ?
O3 C3 C4 111.29(12) . . ?
C2 C3 C4 111.45(12) . . ?
O3 C3 H3 108.2 . . ?
C2 C3 H3 108.2 . . ?
C4 C3 H3 108.2 . . ?
O4A C4 O4B 125.14(14) . . ?
O4A C4 C3 118.92(13) . . ?
O4B C4 C3 115.91(12) . . ?
C2 O2 H2O 109.5 . . ?
C3 O3 H3O 109.5 . . ?
N22 C21 H21A 109.5 . . ?
N22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N22 C23 C24 111.10(12) . . ?
N22 C23 H23A 109.4 . . ?
C24 C23 H23A 109.4 . . ?
N22 C23 H23B 109.4 . . ?
C24 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
N25 C24 C23 110.25(12) . . ?
N25 C24 H24A 109.6 . . ?
C23 C24 H24A 109.6 . . ?
N25 C24 H24B 109.6 . . ?
C23 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
N25 C26 H26A 109.5 . . ?
N25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N22 C27 H27A 109.5 . . ?
N22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N25 C28 H28A 109.5 . . ?
N25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C21 N22 C27 111.43(13) . . ?
C21 N22 C23 109.67(12) . . ?
C27 N22 C23 112.39(12) . . ?
C21 N22 H22 107.7 . . ?
C27 N22 H22 107.7 . . ?
C23 N22 H22 107.7 . . ?
C28 N25 C26 110.56(13) . . ?
C28 N25 C24 113.00(13) . . ?
C26 N25 C24 110.22(12) . . ?
C28 N25 H25 107.6 . . ?
C26 N25 H25 107.6 . . ?
C24 N25 H25 107.6 . . ?
H1W O1W H2W 103(2) . . ?
H21W O2W H22W 103.8(19) . . ?
H31W O3W H32W 103(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 O1A  0.84 2.16 2.6402(18) 116.0 .
O3 H3O O4A  0.84 2.18 2.6427(16) 114.3 .
N25 H25 O4B  0.93 1.74 2.6514(18) 167.1 .
N25 H25 O4A  0.93 2.50 3.120(2) 124.1 .
O1W H1W O1B  0.871(17) 1.888(17) 2.753(3) 172(3) .
O1W H2W O2W  0.845(16) 1.910(17) 2.753(2) 176(3) .
O2W H22W O4B  0.855(16) 1.966(16) 2.816(2) 172(2) .
O2 H2O O1A  0.84 2.10 2.858(2) 150.6 2_656
O3 H3O O1B  0.84 2.15 2.8475(17) 140.5 1_455
N22 H22 O1B  0.93 2.14 3.049(2) 165.8 1_465
N22 H22 O1A  0.93 2.14 2.840(2) 130.7 1_465
O3W H31W O1W  0.854(16) 1.944(17) 2.795(2) 174(3) 1_465
O2W H21W O3W  0.850(16) 1.895(16) 2.743(2) 175(2) 2_567
O3W H32W O1W  0.863(16) 1.937(17) 2.794(2) 172(3) 2_667
 
_diffrn_measured_fraction_theta_max    0.986
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.986
_refine_diff_density_max    0.262
_refine_diff_density_min   -0.375
_refine_diff_density_rms    0.050
