#------------------------------------------------------------------------------
#$Date: 2019-10-28 08:23:29 +0100 (lun 28 de oct de 2019) $
#$Revision: 219800 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/18/2201876.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2201876
loop_
_publ_author_name
'M. Alagar'
'R. V. Krishnakumar'
'M. Subha Nandhini'
'T. S. Cameron'
'S. Natarajan'
_publ_section_title
;
 Bis<small>(DL</small>-aspartic acid) oxalate
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o108
_journal_page_last               o110
_journal_paper_doi               10.1107/S1600536802023334
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          '2C4 H8 N O4 1+, C2 O4 2-'
_chemical_formula_moiety         '2(C4 H8 N O4 1+), C2 O4 2-'
_chemical_formula_sum            'C10 H16 N2 O12'
_chemical_formula_weight         356.24
_chemical_name_common            'DL-aspartic acid hemioxalate'
_chemical_name_systematic        ?
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0
_cell_angle_beta                 99.360(10)
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   7.3870(10)
_cell_length_b                   5.4770(10)
_cell_length_c                   18.522(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39.80
_cell_measurement_theta_min      39.26
_cell_volume                     739.4(2)
_computing_cell_refinement
;
MSC/AFC Diffractometer Control Software
;
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
 1996)
;
_computing_data_reduction
;
TEXSAN for Windows (Molecular Structure Corporation, 1997)
;
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku AFC-5R'
_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  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            2321
_diffrn_reflns_theta_full        30.09
_diffrn_reflns_theta_max         30.09
_diffrn_reflns_theta_min         2.84
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      1.61
_exptl_crystal_density_method
'flotation in a mixture of xylene and bromoform'
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.356
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         2171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0959P)²+0.3684P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1930
_reflns_number_gt                1191
_reflns_number_total             2171
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6191.cif
_cod_data_source_block           I
_cod_depositor_comments
;

2019-10-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C5 H8 N O6'
_cod_original_formula_weight         178.12
_cod_original_formula_moiety         'C4 H8 N O4 1+, 0.5C2 O4 2-'
_cod_original_formula_iupac          'C4 H8 N O4 1+, 0.5C2 O4 2-'
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2201876
_cod_database_fobs_code          2201876
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
O1 0.2183(3) 0.8831(4) 0.93073(11) 0.0458(5) Uani d . 1 . . O
H1 0.2570 1.0079 0.9523 0.069 Uiso calc R 1 . . H
O2 -0.0508(3) 1.0786(3) 0.91478(11) 0.0442(5) Uani d . 1 . . O
O3 0.0634(4) 0.5955(4) 0.69742(10) 0.0547(6) Uani d . 1 . . O
H3 0.0421 0.6843 0.6614 0.082 Uiso calc R 1 . . H
O4 -0.0869(3) 0.8853(4) 0.74711(10) 0.0480(5) Uani d . 1 . . O
O5 0.4943(3) 0.6218(4) 0.08590(9) 0.0431(5) Uani d . 1 . . O
O6 0.6566(3) 0.7363(4) 0.00140(10) 0.0489(6) Uani d . 1 . . O
N1 -0.2429(3) 0.6923(5) 0.86635(11) 0.0426(6) Uani d . 1 . . N
H1A -0.2961 0.5525 0.8502 0.064 Uiso calc R 1 . . H
H1B -0.2676 0.8062 0.8319 0.064 Uiso calc R 1 . . H
H1C -0.2859 0.7397 0.9063 0.064 Uiso calc R 1 . . H
C1 0.0416(3) 0.8988(4) 0.91156(12) 0.0313(5) Uani d . 1 . . C
C2 -0.0412(4) 0.6565(4) 0.88420(12) 0.0314(5) Uani d . 1 . . C
H2 -0.0180 0.5403 0.9249 0.038 Uiso calc R 1 . . H
C3 0.0402(4) 0.5495(4) 0.82089(12) 0.0344(5) Uani d . 1 . . C
H3A 0.1722 0.5380 0.8351 0.041 Uiso calc R 1 . . H
H3B -0.0069 0.3853 0.8114 0.041 Uiso calc R 1 . . H
C4 -0.0010(3) 0.6954(4) 0.75167(12) 0.0324(5) Uani d . 1 . . C
C5 0.5432(3) 0.6033(4) 0.02542(12) 0.0301(5) Uani d . 1 . . C
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0421(10) 0.0444(11) 0.0502(11) -0.0088(8) 0.0051(9) -0.0195(9)
O2 0.0526(11) 0.0283(9) 0.0518(11) -0.0028(8) 0.0087(9) -0.0013(8)
O3 0.0939(17) 0.0446(11) 0.0312(10) 0.0182(11) 0.0269(10) 0.0083(8)
O4 0.0622(13) 0.0525(12) 0.0327(10) 0.0206(10) 0.0173(9) 0.0153(8)
O5 0.0590(12) 0.0467(11) 0.0282(8) -0.0185(9) 0.0206(8) -0.0161(8)
O6 0.0573(12) 0.0558(13) 0.0393(10) -0.0347(10) 0.0246(9) -0.0213(9)
N1 0.0475(13) 0.0549(14) 0.0278(10) -0.0213(11) 0.0135(9) -0.0079(9)
C1 0.0426(13) 0.0273(11) 0.0250(10) -0.0091(10) 0.0083(9) -0.0008(8)
C2 0.0457(13) 0.0274(11) 0.0207(9) -0.0107(10) 0.0047(9) 0.0011(8)
C3 0.0548(14) 0.0260(11) 0.0219(10) -0.0016(10) 0.0051(9) 0.0023(8)
C4 0.0401(13) 0.0331(12) 0.0253(10) -0.0040(10) 0.0089(9) 0.0035(9)
C5 0.0299(11) 0.0346(12) 0.0267(10) -0.0072(9) 0.0077(8) -0.0080(9)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C1 O1 H1 . 109.5
C4 O3 H3 . 109.5
C2 N1 H1A . 109.5
C2 N1 H1B . 109.5
H1A N1 H1B . 109.5
C2 N1 H1C . 109.5
H1A N1 H1C . 109.5
H1B N1 H1C . 109.5
O2 C1 O1 . 126.4(2)
O2 C1 C2 . 122.1(2)
O1 C1 C2 . 111.5(2)
N1 C2 C1 . 107.1(2)
N1 C2 C3 . 112.81(19)
C1 C2 C3 . 114.0(2)
N1 C2 H2 . 107.5
C1 C2 H2 . 107.5
C3 C2 H2 . 107.5
C4 C3 C2 . 113.8(2)
C4 C3 H3A . 108.8
C2 C3 H3A . 108.8
C4 C3 H3B . 108.8
C2 C3 H3B . 108.8
H3A C3 H3B . 107.7
O4 C4 O3 . 124.0(2)
O4 C4 C3 . 123.2(2)
O3 C4 C3 . 112.8(2)
O5 C5 O6 . 126.0(2)
O5 C5 C5 3_665 117.4(2)
O6 C5 C5 3_665 116.5(2)
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 C1 . 1.299(3) ?
O1 H1 . 0.82 ?
O2 C1 . 1.205(3) ?
O3 C4 . 1.300(3) ?
O3 H3 . 0.82 ?
O4 C4 . 1.214(3) ?
O5 C5 . 1.236(3) ?
O6 C5 . 1.246(3) ?
N1 C2 . 1.486(3) ?
N1 H1A . 0.89 ?
N1 H1B . 0.89 ?
N1 H1C . 0.89 ?
C1 C2 . 1.514(3) ?
C2 C3 . 1.520(3) ?
C2 H2 . 0.98 ?
C3 C4 . 1.499(3) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C5 C5 3_665 1.542(4) ?
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
O1 H1 O6 3_676 0.82 1.71 2.530(3) 178
O3 H3 O5 4_576 0.82 1.75 2.565(2) 179
N1 H1A O4 2_446 0.89 2.08 2.822(3) 140
N1 H1B O4 . 0.89 2.26 2.855(3) 124
N1 H1C O6 1_456 0.89 1.88 2.733(3) 160
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
O2 C1 C2 N1 -1.3(3)
O1 C1 C2 N1 178.05(19)
O2 C1 C2 C3 124.2(3)
O1 C1 C2 C3 -56.4(3)
N1 C2 C3 C4 55.8(3)
C1 C2 C3 C4 -66.7(3)
C2 C3 C4 O4 2.0(4)
C2 C3 C4 O3 -177.3(2)
