#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/02/1520244.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1520244
loop_
_publ_author_name
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 DL-tartaric acid + TEMED
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              452
_journal_year                    2008
_chemical_formula_sum            'C10 H28 N2 O9'
_chemical_formula_weight         320.34
_chemical_name_systematic
;
DL-Tartaric acid & TEMED trihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.92(3)
_cell_angle_beta                 91.41(3)
_cell_angle_gamma                99.79(2)
_cell_formula_units_Z            2
_cell_length_a                   6.1179(14)
_cell_length_b                   8.672(2)
_cell_length_c                   15.182(8)
_cell_measurement_reflns_used    3376
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     793.3(5)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12962
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.38
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0479P)²+0.3813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                2759
_reflns_number_total             3575
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-452.cif
_cod_data_source_block           04mbh0608
_cod_depositor_comments
;
Citation :
Callear, Samantha K. and Hursthouse, Michael B. (2008) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/452)

More at:
http://ecrystals.chem.soton.ac.uk/452/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1520244
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 . .
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'
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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_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
