 
data_04skc0004p-1
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
DL-Tartaric Acid & Morpholine
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C8 H17 N O8'
_chemical_formula_weight          255.23
 
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            Triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.6152(7)
_cell_length_b                    8.2002(11)
_cell_length_c                    10.1113(12)
_cell_angle_alpha                 98.680(10)
_cell_angle_beta                  106.417(8)
_cell_angle_gamma                 105.156(8)
_cell_volume                      567.11(11)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2511
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.18
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.495
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              272
_exptl_absorpt_coefficient_mu     0.135
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9481
_exptl_absorpt_correction_T_max   0.9761
_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             12484
_diffrn_reflns_av_R_equivalents   0.0299
_diffrn_reflns_av_sigmaI/netI     0.0258
_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        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          2.94
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2591
_reflns_number_gt                 2159
_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)+(0.0462P)²+0.1866P] 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          2591
_refine_ls_number_parameters      165
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.0474
_refine_ls_R_factor_gt            0.0358
_refine_ls_wR_factor_ref          0.0939
_refine_ls_wR_factor_gt           0.0869
_refine_ls_goodness_of_fit_ref    1.053
_refine_ls_restrained_S_all       1.053
_refine_ls_shift/su_max           0.003
_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 -0.39248(17) 0.18708(15) 0.63598(13) 0.0146(3) Uani 1 1 d . . .
C2 C -0.22552(17) 0.15338(15) 0.59431(13) 0.0137(2) Uani 1 1 d . . .
H2 H -0.2756 0.0873 0.4925 0.016 Uiso 1 1 calc R . .
C3 C -0.06942(16) 0.32448(15) 0.61290(12) 0.0127(2) Uani 1 1 d . . .
H3 H -0.1302 0.3924 0.5503 0.015 Uiso 1 1 calc R . .
C4 C 0.08794(17) 0.28274(15) 0.56014(13) 0.0137(2) Uani 1 1 d . . .
O1A O -0.44448(13) 0.12846(12) 0.72635(10) 0.0220(2) Uani 1 1 d . . .
O1B O -0.47472(12) 0.28053(12) 0.56008(10) 0.0195(2) Uani 1 1 d . . .
H1 H -0.5671 0.2943 0.5852 0.029 Uiso 1 1 calc R . .
O2 O -0.14853(13) 0.05095(11) 0.68075(9) 0.0166(2) Uani 1 1 d . . .
H2O H -0.1147 -0.0202 0.6329 0.025 Uiso 1 1 calc R . .
O3 O 0.00153(12) 0.42563(10) 0.75448(9) 0.01444(19) Uani 1 1 d . . .
H3O H 0.0625 0.3754 0.8083 0.022 Uiso 1 1 calc R . .
O4A O 0.02972(13) 0.18951(11) 0.43541(9) 0.0175(2) Uani 1 1 d . . .
O4B O 0.25840(12) 0.34217(12) 0.64233(10) 0.0224(2) Uani 1 1 d . . .
C22 C 0.2834(2) 0.31109(17) 1.21080(14) 0.0208(3) Uani 1 1 d . . .
H22B H 0.3487 0.3833 1.3094 0.025 Uiso 1 1 calc R . .
H22A H 0.1436 0.2633 1.1953 0.025 Uiso 1 1 calc R . .
C23 C 0.3135(2) 0.42125(17) 1.10773(14) 0.0219(3) Uani 1 1 d . . .
H23B H 0.2553 0.5149 1.1190 0.026 Uiso 1 1 calc R . .
H23A H 0.4537 0.4763 1.1284 0.026 Uiso 1 1 calc R . .
C25 C 0.3161(2) 0.1863(2) 0.94401(15) 0.0284(3) Uani 1 1 d . . .
H25B H 0.4561 0.2423 0.9648 0.034 Uiso 1 1 calc R . .
H25A H 0.2589 0.1192 0.8435 0.034 Uiso 1 1 calc R . .
C26 C 0.28704(19) 0.06514(17) 1.03930(14) 0.0211(3) Uani 1 1 d . . .
H26B H 0.1476 0.0015 1.0131 0.025 Uiso 1 1 calc R . .
H26A H 0.3544 -0.0213 1.0271 0.025 Uiso 1 1 calc R . .
N21 N 0.36405(16) 0.16553(13) 1.18956(11) 0.0179(2) Uani 1 1 d . . .
H21A H 0.4965 0.2102 1.2174 0.021 Uiso 1 1 calc R . .
H21B H 0.3340 0.0920 1.2460 0.021 Uiso 1 1 calc R . .
O24 O 0.22727(16) 0.31720(14) 0.96530(10) 0.0309(3) Uani 1 1 d . . .
O1W O 0.24959(13) -0.24702(12) 0.77433(11) 0.0223(2) Uani 1 1 d D . .
H1W H 0.170(3) -0.216(2) 0.7115(19) 0.047(6) Uiso 1 1 d D . .
H2W H 0.187(3) -0.349(2) 0.773(2) 0.042(5) 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 1.2085(16) . ?
C1 O1B 1.3135(16) . ?
C1 C2 1.5237(16) . ?
C2 O2 1.4152(15) . ?
C2 C3 1.5294(17) . ?
C2 H2 1.0000 . ?
C3 O3 1.4140(14) . ?
C3 C4 1.5358(16) . ?
C3 H3 1.0000 . ?
C4 O4B 1.2452(15) . ?
C4 O4A 1.2598(15) . ?
O1B H1 0.8400 . ?
O2 H2O 0.8400 . ?
O3 H3O 0.8400 . ?
C22 N21 1.4928(16) . ?
C22 C23 1.5052(19) . ?
C22 H22B 0.9900 . ?
C22 H22A 0.9900 . ?
C23 O24 1.4265(16) . ?
C23 H23B 0.9900 . ?
C23 H23A 0.9900 . ?
C25 O24 1.4313(16) . ?
C25 C26 1.503(2) . ?
C25 H25B 0.9900 . ?
C25 H25A 0.9900 . ?
C26 N21 1.4821(17) . ?
C26 H26B 0.9900 . ?
C26 H26A 0.9900 . ?
N21 H21A 0.9200 . ?
N21 H21B 0.9200 . ?
O1W H1W 0.865(14) . ?
O1W H2W 0.845(14) . ?
 
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 124.82(11) . . ?
O1A C1 C2 122.61(11) . . ?
O1B C1 C2 112.53(11) . . ?
O2 C2 C1 108.09(10) . . ?
O2 C2 C3 110.48(10) . . ?
C1 C2 C3 111.00(10) . . ?
O2 C2 H2 109.1 . . ?
C1 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
O3 C3 C2 111.22(10) . . ?
O3 C3 C4 113.74(10) . . ?
C2 C3 C4 108.59(9) . . ?
O3 C3 H3 107.7 . . ?
C2 C3 H3 107.7 . . ?
C4 C3 H3 107.7 . . ?
O4B C4 O4A 126.12(11) . . ?
O4B C4 C3 118.26(11) . . ?
O4A C4 C3 115.62(10) . . ?
C1 O1B H1 109.5 . . ?
C2 O2 H2O 109.5 . . ?
C3 O3 H3O 109.5 . . ?
N21 C22 C23 109.52(10) . . ?
N21 C22 H22B 109.8 . . ?
C23 C22 H22B 109.8 . . ?
N21 C22 H22A 109.8 . . ?
C23 C22 H22A 109.8 . . ?
H22B C22 H22A 108.2 . . ?
O24 C23 C22 110.38(11) . . ?
O24 C23 H23B 109.6 . . ?
C22 C23 H23B 109.6 . . ?
O24 C23 H23A 109.6 . . ?
C22 C23 H23A 109.6 . . ?
H23B C23 H23A 108.1 . . ?
O24 C25 C26 110.38(11) . . ?
O24 C25 H25B 109.6 . . ?
C26 C25 H25B 109.6 . . ?
O24 C25 H25A 109.6 . . ?
C26 C25 H25A 109.6 . . ?
H25B C25 H25A 108.1 . . ?
N21 C26 C25 109.94(11) . . ?
N21 C26 H26B 109.7 . . ?
C25 C26 H26B 109.7 . . ?
N21 C26 H26A 109.7 . . ?
C25 C26 H26A 109.7 . . ?
H26B C26 H26A 108.2 . . ?
C26 N21 C22 111.91(10) . . ?
C26 N21 H21A 109.2 . . ?
C22 N21 H21A 109.2 . . ?
C26 N21 H21B 109.2 . . ?
C22 N21 H21B 109.2 . . ?
H21A N21 H21B 107.9 . . ?
C23 O24 C25 110.73(10) . . ?
H1W O1W H2W 104.3(16) . . ?
 
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 O24  0.84 1.93 2.7549(13) 165.5 .
N21 H21A O1W  0.92 1.85 2.7436(15) 162.4 2_657
N21 H21B O2  0.92 1.98 2.8213(14) 151.9 2_557
N21 H21B O1A  0.92 2.21 2.8295(14) 124.3 2_557
O1B H1 O4B  0.84 1.70 2.5383(12) 174.6 1_455
O2 H2O O4A  0.84 1.80 2.6307(12) 167.6 2_556
O1W H1W O4A  0.865(14) 1.886(15) 2.7424(13) 170.2(18) 2_556
O1W H2W O3  0.845(14) 1.954(15) 2.7904(13) 170.0(17) 1_545
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.282
_refine_diff_density_min   -0.283
_refine_diff_density_rms    0.050
