#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/73/2227303.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_2227303
loop_
_publ_author_name
'Natarajan, S.'
'Hema, V.'
'Sundar, J. Kalyana'
'Suresh, J.'
'Lakshman, P. L. Nilantha'
_publ_section_title
;
 <small>L</small>-Asparagine--<small>L</small>-tartaric acid (1/1)
;
_journal_coeditor_code           CI5134
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2239
_journal_paper_doi               10.1107/S1600536810030771
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C4 H8 N2 O3, C4 H6 O6'
_chemical_formula_moiety         'C4 H8 N2 O3, C4 H6 O6'
_chemical_formula_sum            'C8 H14 N2 O9'
_chemical_formula_weight         282.21
_chemical_name_common
;
L-Asparagine--L-tartaric acid (1/1)
;
_chemical_name_systematic
;
2-Ammonio-3-carbamoylpropanoate--2,3-dihydroxybutanedioic acid (1/1)
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.311(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.0860(4)
_cell_length_b                   9.6720(6)
_cell_length_c                   11.8340(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.7
_cell_volume                     579.64(7)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1996)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius MACH-3'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0953
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            1339
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.9693
_exptl_absorpt_correction_T_min  0.9594
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.398
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.378
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1073
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.377
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1143P)²+0.7291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2201
_refine_ls_wR_factor_ref         0.2255
_reflns_number_gt                1015
_reflns_number_total             1073
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5134.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2227303
_cod_database_fobs_code          2227303
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.0957(12) 0.4538(7) 0.1832(5) 0.0531(18) Uani d . 1 . .
O O2 0.7732(11) 0.5170(7) 0.5295(5) 0.0459(16) Uani d . 1 . .
O O3 0.5946(13) 0.3196(8) 0.5798(5) 0.0544(18) Uani d . 1 . .
N N1 0.0876(12) 0.6710(7) 0.2495(5) 0.0377(16) Uani d . 1 . .
H H1A -0.0578 0.6889 0.2091 0.045 Uiso calc R 1 . .
H H1B 0.1622 0.7336 0.2930 0.045 Uiso calc R 1 . .
N N2 0.2460(11) 0.3066(7) 0.4019(5) 0.0322(14) Uani d . 1 . .
H H2A 0.0730 0.3170 0.3847 0.039 Uiso calc R 1 . .
H H2B 0.2741 0.2509 0.4617 0.039 Uiso calc R 1 . .
H H2C 0.3176 0.2698 0.3430 0.039 Uiso calc R 1 . .
C C1 0.6013(12) 0.4214(8) 0.5193(5) 0.0280(15) Uani d . 1 . .
C C2 0.3687(13) 0.4442(8) 0.4293(5) 0.0263(15) Uani d . 1 . .
H H2 0.2378 0.5013 0.4633 0.032 Uiso calc R 1 . .
C C3 0.4415(14) 0.5175(8) 0.3216(6) 0.0333(17) Uani d . 1 . .
H H3A 0.5336 0.6030 0.3420 0.040 Uiso calc R 1 . .
H H3B 0.5585 0.4592 0.2822 0.040 Uiso calc R 1 . .
C C4 0.1954(14) 0.5483(8) 0.2447(6) 0.0328(16) Uani d . 1 . .
O O4 0.2756(10) -0.0470(6) -0.0292(4) 0.0378(13) Uani d . 1 . .
H H4 0.1664 -0.0392 -0.0843 0.057 Uiso calc R 1 . .
O O5 0.4110(10) 0.1599(6) -0.0849(5) 0.0396(14) Uani d . 1 . .
O O6 0.8377(9) 0.1558(6) 0.0676(4) 0.0355(13) Uani d . 1 . .
H H6 0.7635 0.2283 0.0478 0.053 Uiso calc R 1 . .
O O7 0.3467(9) 0.1735(7) 0.1895(4) 0.0385(14) Uani d . 1 . .
H H7 0.2136 0.1605 0.1462 0.058 Uiso calc R 1 . .
O O8 0.7364(9) 0.1781(7) 0.3463(5) 0.0418(15) Uani d . 1 . .
O O9 0.9010(10) -0.0231(6) 0.2943(5) 0.0378(14) Uani d . 1 . .
H H9 1.0049 -0.0102 0.3505 0.057 Uiso calc R 1 . .
C C5 0.4314(12) 0.0606(9) -0.0232(5) 0.0283(15) Uani d . 1 . .
C C6 0.6460(13) 0.0500(8) 0.0750(6) 0.0269(15) Uani d . 1 . .
H H6A 0.7333 -0.0400 0.0712 0.032 Uiso calc R 1 . .
C C7 0.5159(12) 0.0584(8) 0.1865(6) 0.0296(15) Uani d . 1 . .
H H7A 0.4173 -0.0268 0.1977 0.035 Uiso calc R 1 . .
C C8 0.7309(12) 0.0778(8) 0.2842(5) 0.0274(16) Uani d . 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 N1 H1A . . 120.0 ?
C4 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
C2 N2 H2A . . 109.5 ?
C2 N2 H2B . . 109.5 ?
H2A N2 H2B . . 109.5 ?
C2 N2 H2C . . 109.5 ?
H2A N2 H2C . . 109.5 ?
H2B N2 H2C . . 109.5 ?
O3 C1 O2 . . 126.0(6) ?
O3 C1 C2 . . 117.5(6) ?
O2 C1 C2 . . 116.2(7) ?
N2 C2 C3 . . 111.1(5) ?
N2 C2 C1 . . 107.6(6) ?
C3 C2 C1 . . 114.5(5) ?
N2 C2 H2 . . 107.8 ?
C3 C2 H2 . . 107.8 ?
C1 C2 H2 . . 107.8 ?
C4 C3 C2 . . 110.0(6) ?
C4 C3 H3A . . 109.7 ?
C2 C3 H3A . . 109.7 ?
C4 C3 H3B . . 109.7 ?
C2 C3 H3B . . 109.7 ?
H3A C3 H3B . . 108.2 ?
O1 C4 N1 . . 122.6(6) ?
O1 C4 C3 . . 118.6(7) ?
N1 C4 C3 . . 118.7(7) ?
C5 O4 H4 . . 109.5 ?
C6 O6 H6 . . 109.5 ?
C7 O7 H7 . . 109.5 ?
C8 O9 H9 . . 109.5 ?
O5 C5 O4 . . 125.7(6) ?
O5 C5 C6 . . 122.1(7) ?
O4 C5 C6 . . 112.1(6) ?
O6 C6 C5 . . 110.6(6) ?
O6 C6 C7 . . 111.6(6) ?
C5 C6 C7 . . 108.5(5) ?
O6 C6 H6A . . 108.7 ?
C5 C6 H6A . . 108.7 ?
C7 C6 H6A . . 108.7 ?
O7 C7 C8 . . 106.3(6) ?
O7 C7 C6 . . 112.2(6) ?
C8 C7 C6 . . 108.8(5) ?
O7 C7 H7A . . 109.8 ?
C8 C7 H7A . . 109.8 ?
C6 C7 H7A . . 109.8 ?
O8 C8 O9 . . 124.4(6) ?
O8 C8 C7 . . 122.0(6) ?
O9 C8 C7 . . 113.6(6) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.247(10) ?
O2 C1 . 1.271(10) ?
O3 C1 . 1.219(10) ?
N1 C4 . 1.311(11) ?
N1 H1A . 0.86 ?
N1 H1B . 0.86 ?
N2 C2 . 1.492(10) ?
N2 H2A . 0.89 ?
N2 H2B . 0.89 ?
N2 H2C . 0.89 ?
C1 C2 . 1.533(9) ?
C2 C3 . 1.533(10) ?
C2 H2 . 0.98 ?
C3 C4 . 1.507(9) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
O4 C5 . 1.306(10) ?
O4 H4 . 0.82 ?
O5 C5 . 1.205(10) ?
O6 C6 . 1.422(9) ?
O6 H6 . 0.82 ?
O7 C7 . 1.409(9) ?
O7 H7 . 0.82 ?
O8 C8 . 1.215(9) ?
O9 C8 . 1.302(9) ?
O9 H9 . 0.82 ?
C5 C6 . 1.522(9) ?
C6 C7 . 1.532(10) ?
C6 H6A . 0.98 ?
C7 C8 . 1.528(8) ?
C7 H7A . 0.98 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O5 2 0.86 2.23 3.053(8) 160
N1 H1B O3 2_656 0.86 2.04 2.856(9) 159
N2 H2A O8 1_455 0.89 2.19 2.895(8) 136
N2 H2B O2 2_646 0.89 2.28 2.921(9) 129
N2 H2C O7 . 0.89 2.06 2.912(8) 160
N2 H2C O8 . 0.89 2.30 2.916(8) 126
O4 H4 O1 2_545 0.82 1.69 2.500(6) 168
O6 H6 O4 2_655 0.82 2.19 2.959(8) 156
O7 H7 O6 1_455 0.82 2.05 2.850(7) 166
O9 H9 O2 2_746 0.82 1.75 2.570(7) 180
C2 H2 O2 1_455 0.98 2.56 3.426(9) 147
C3 H3A O3 2_656 0.97 2.40 3.158(10) 134
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 C1 C2 N2 . . . . -24.9(9) ?
O2 C1 C2 N2 . . . . 160.4(6) ?
O3 C1 C2 C3 . . . . -149.0(7) ?
O2 C1 C2 C3 . . . . 36.4(9) ?
N2 C2 C3 C4 . . . . 63.9(8) ?
C1 C2 C3 C4 . . . . -173.9(6) ?
C2 C3 C4 O1 . . . . -80.7(9) ?
C2 C3 C4 N1 . . . . 95.9(8) ?
O5 C5 C6 O6 . . . . -11.4(9) ?
O4 C5 C6 O6 . . . . 170.0(6) ?
O5 C5 C6 C7 . . . . 111.3(8) ?
O4 C5 C6 C7 . . . . -67.4(8) ?
O6 C6 C7 O7 . . . . 70.9(7) ?
C5 C6 C7 O7 . . . . -51.2(8) ?
O6 C6 C7 C8 . . . . -46.4(8) ?
C5 C6 C7 C8 . . . . -168.5(6) ?
O7 C7 C8 O8 . . . . -0.7(9) ?
C6 C7 C8 O8 . . . . 120.3(7) ?
O7 C7 C8 O9 . . . . 178.5(6) ?
C6 C7 C8 O9 . . . . -60.6(8) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656198
