#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/55/2105595.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_2105595
loop_
_publ_author_name
'Chandra, N. R.'
'Prabu, M. M.'
'Venkatraman, J.'
'Suresh, S.'
'Vijayan, M.'
_publ_section_title
;
 X-ray Studies on Crystalline Complexes Involving Amino Acids and
 Peptides. XXXIII. Crystal Structures of <small>L</small>- and
 <small>DL</small>-Arginine Complexed with Oxalic Acid and a Comparative
 Study of Amino Acid--Oxalic Acid Complexes
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              257
_journal_page_last               263
_journal_paper_doi               10.1107/S0108768197011543
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C6 H15 N4 O2. C2 H O4'
_chemical_formula_sum            'C8 H16 N4 O6'
_chemical_formula_weight         264.25
_chemical_name_common            'L-Arginine semi-oxalate'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                111.11(2)
_cell_angle_beta                 92.75(2)
_cell_angle_gamma                91.97(3)
_cell_formula_units_Z            2
_cell_length_a                   5.0668(14)
_cell_length_b                   9.7572(13)
_cell_length_c                   13.141(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      5
_cell_volume                     604.4(2)
_computing_cell_refinement       'Enraf-Nonius CAD4 built-in software'
_computing_data_collection       'Enraf-Nonius CAD4 built-in software'
_computing_data_reduction        'locally written software'
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1994)'
_computing_publication_material  MS-WORD
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71068
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2771
_diffrn_reflns_theta_max         24.68
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        7.2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         .304
_refine_diff_density_min         -.222
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.025
_refine_ls_goodness_of_fit_obs   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         2379
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.024
_refine_ls_restrained_S_obs      1.024
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_obs          0.0343
_refine_ls_shift/esd_max         -0.013
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+( 0.0641P)²+0.1211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0968
_refine_ls_wR_factor_obs         0.0896
_reflns_number_observed          2084
_reflns_number_total             2379
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            li0261.cif
_cod_data_source_block           LAO
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(
0.0641P)^2^+0.1211P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'.
New tag '_refine_ls_weighting_details' was created. The value of the
new tag was set to 'w = 1/[\s^2^(Fo^2^)+( 0.0641P)^2^+0.1211P] where
P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2105595
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
N1 0.4167(6) -0.0163(3) 0.8579(2) 0.0292(6) Uani d . 1 N
H1A 0.387(9) -0.103(5) 0.837(3) 0.044 Uiso d . 1 H
H1B 0.487(9) 0.008(4) 0.932(3) 0.044 Uiso d . 1 H
H1C 0.531(9) 0.002(5) 0.816(3) 0.044 Uiso d . 1 H
O2 -0.1958(5) 0.0305(3) 0.7273(2) 0.0377(6) Uani d . 1 O
O1 0.0767(5) -0.1540(3) 0.6942(2) 0.0421(6) Uani d . 1 O
C1 0.0090(7) -0.0265(4) 0.7468(3) 0.0296(7) Uani d . 1 C
C2 0.1871(7) 0.0674(4) 0.8464(3) 0.0273(7) Uani d . 1 C
HC2 0.0860(7) 0.0875(4) 0.9115(3) 0.033 Uiso calc R 1 H
C3 0.2759(7) 0.2132(3) 0.8389(3) 0.0308(7) Uani d . 1 C
H3A 0.1215(7) 0.2611(3) 0.8244(3) 0.037 Uiso calc R 1 H
H3B 0.3867(7) 0.1948(3) 0.7777(3) 0.037 Uiso calc R 1 H
C4 0.4295(8) 0.3172(4) 0.9425(3) 0.0372(8) Uani d . 1 C
H4A 0.5786(8) 0.2676(4) 0.9594(3) 0.045 Uiso calc R 1 H
H4B 0.3155(8) 0.3405(4) 1.0031(3) 0.045 Uiso calc R 1 H
C5 0.5307(8) 0.4600(4) 0.9314(3) 0.0394(9) Uani d . 1 C
H5A 0.6026(8) 0.5268(4) 1.0023(3) 0.047 Uiso calc R 1 H
H5B 0.6738(8) 0.4385(4) 0.8825(3) 0.047 Uiso calc R 1 H
N6 0.3300(7) 0.5333(3) 0.8902(2) 0.0360(7) Uani d . 1 N
H6 0.2937(7) 0.5003(3) 0.8207(2) 0.043 Uiso calc R 1 H
C7 0.1981(6) 0.6459(3) 0.9496(3) 0.0279(7) Uani d . 1 C
N8 0.1951(7) 0.6876(3) 1.0569(2) 0.0399(7) Uani d . 1 N
H8A 0.2813(7) 0.6408(3) 1.0908(2) 0.048 Uiso calc R 1 H
H8B 0.1069(7) 0.7615(3) 1.0928(2) 0.048 Uiso calc R 1 H
N9 0.0681(6) 0.7212(3) 0.8986(2) 0.0373(7) Uani d . 1 N
H9A -0.0167(6) 0.7961(3) 0.9355(2) 0.045 Uiso calc R 1 H
H9B 0.0687(6) 0.6950(3) 0.8287(2) 0.045 Uiso calc R 1 H
O21 0.5801(5) 0.6817(3) 0.7506(2) 0.0406(6) Uani d . 1 O
O22 0.6999(5) 0.6614(3) 0.5860(2) 0.0396(6) Uani d . 1 O
H22 0.805(11) 0.726(6) 0.626(4) 0.059 Uiso d . 1 H
C23 0.5480(7) 0.6294(3) 0.6527(3) 0.0289(7) Uani d . 1 C
C24 0.3176(7) 0.5152(4) 0.5947(3) 0.0343(8) Uani d . 1 C
O25 0.1944(6) 0.4665(3) 0.6545(2) 0.0524(8) Uani d . 1 O
O26 0.2768(5) 0.4819(3) 0.4941(2) 0.0404(6) Uani d . 1 O
N11 0.7332(7) 0.4334(3) 0.3667(2) 0.0336(7) Uani d . 1 N
H11C 0.707(9) 0.331(5) 0.337(3) 0.050 Uiso d . 1 H
H11B 0.594(10) 0.473(5) 0.412(4) 0.050 Uiso d . 1 H
H11A 0.887(10) 0.451(5) 0.418(4) 0.050 Uiso d . 1 H
O11 1.0380(6) 0.2917(3) 0.2114(2) 0.0537(8) Uani d . 1 O
O12 1.1544(7) 0.4876(3) 0.1748(3) 0.0595(9) Uani d . 1 O
C11 1.0146(7) 0.4213(4) 0.2169(3) 0.0307(7) Uani d . 1 C
C12 0.7853(7) 0.4998(3) 0.2828(3) 0.0284(7) Uani d . 1 C
HC12 0.6272(7) 0.4799(3) 0.2326(3) 0.034 Uiso calc R 1 H
C13 0.8306(7) 0.6644(4) 0.3372(3) 0.0324(7) Uani d . 1 C
H13A 0.9167(7) 0.7021(4) 0.2876(3) 0.039 Uiso calc R 1 H
H13B 0.9494(7) 0.6859(4) 0.4018(3) 0.039 Uiso calc R 1 H
C14 0.5765(7) 0.7445(4) 0.3705(3) 0.0318(7) Uani d . 1 C
H14A 0.4783(7) 0.7453(4) 0.3056(3) 0.038 Uiso calc R 1 H
H14B 0.4675(7) 0.6908(4) 0.4040(3) 0.038 Uiso calc R 1 H
C15 0.6286(8) 0.9012(4) 0.4498(3) 0.0354(8) Uani d . 1 C
H15A 0.4626(8) 0.9493(4) 0.4642(3) 0.043 Uiso calc R 1 H
H15B 0.7075(8) 0.9009(4) 0.5184(3) 0.043 Uiso calc R 1 H
N16 0.8054(7) 0.9823(3) 0.4048(2) 0.0349(7) Uani d . 1 N
H16 0.8346(7) 0.9431(3) 0.3366(2) 0.042 Uiso calc R 1 H
C17 0.9233(7) 1.1111(3) 0.4611(3) 0.0291(7) Uani d . 1 C
N18 0.9102(8) 1.1748(3) 0.5681(2) 0.0476(9) Uani d . 1 N
H18A 0.8218(8) 1.1317(3) 0.6034(2) 0.057 Uiso calc R 1 H
H18B 0.9900(8) 1.2594(3) 0.6024(2) 0.057 Uiso calc R 1 H
N19 1.0606(7) 1.1796(3) 0.4096(3) 0.0462(8) Uani d . 1 N
H19A 1.0721(7) 1.1398(3) 0.3401(3) 0.055 Uiso calc R 1 H
H19B 1.1390(7) 1.2641(3) 0.4455(3) 0.055 Uiso calc R 1 H
O32 0.3748(6) 0.1247(3) 0.1053(2) 0.0436(7) Uani d . 1 O
H32 0.258(11) 0.194(5) 0.140(4) 0.065 Uiso d . 1 H
O31 0.5177(6) 0.1316(3) 0.2697(2) 0.0422(6) Uani d . 1 O
C33 0.5244(7) 0.0840(4) 0.1705(3) 0.0307(7) Uani d . 1 C
C34 0.7271(7) -0.0295(4) 0.1137(3) 0.0338(8) Uani d . 1 C
O36 0.7400(6) -0.0591(3) 0.0141(2) 0.0506(8) Uani d . 1 O
O35 0.8582(6) -0.0800(3) 0.1729(2) 0.0467(7) Uani d . 1 O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
_geom_angle_publ_flag
C2 N1 H1A 114.(3) y
C2 N1 H1B 114.(3) y
H1A N1 H1B 104.(4) y
C2 N1 H1C 104.(3) y
H1A N1 H1C 108.(4) y
H1B N1 H1C 113.(4) y
O2 C1 O1 126.2(3) y
O2 C1 C2 116.3(3) y
O1 C1 C2 117.5(3) y
N1 C2 C3 111.0(3) y
N1 C2 C1 109.3(3) y
C3 C2 C1 111.8(3) y
N1 C2 HC2 108.2(2) y
C3 C2 HC2 108.2(2) y
C1 C2 HC2 108.2(2) y
C2 C3 C4 113.3(3) y
C2 C3 H3A 108.9(2) y
C4 C3 H3A 108.9(2) y
C2 C3 H3B 108.9(2) y
C4 C3 H3B 108.9(2) y
H3A C3 H3B 107.7 y
C3 C4 C5 112.7(3) y
C3 C4 H4A 109.1(2) y
C5 C4 H4A 109.1(2) y
C3 C4 H4B 109.1(2) y
C5 C4 H4B 109.1(2) y
H4A C4 H4B 107.8 y
N6 C5 C4 114.1(3) y
N6 C5 H5A 108.7(2) y
C4 C5 H5A 108.7(2) y
N6 C5 H5B 108.7(2) y
C4 C5 H5B 108.7(2) y
H5A C5 H5B 107.6 y
C7 N6 C5 126.1(3) y
C7 N6 H6 116.9(2) y
C5 N6 H6 116.9(2) y
N8 C7 N6 122.6(3) y
N8 C7 N9 119.2(3) y
N6 C7 N9 118.1(3) y
C7 N8 H8A 120.0(2) y
C7 N8 H8B 120.0(2) y
H8A N8 H8B 120.0 y
C7 N9 H9A 120.0(2) y
C7 N9 H9B 120.0(2) y
H9A N9 H9B 120.0 y
C23 O22 H22 105.(4) y
O21 C23 O22 124.2(3) y
O21 C23 C24 121.7(3) y
O22 C23 C24 114.0(3) y
O25 C24 O26 127.2(3) y
O25 C24 C23 115.4(3) y
O26 C24 C23 117.4(3) y
C12 N11 H11C 113.(2) y
C12 N11 H11B 115.(3) y
H11C N11 H11B 109.(4) y
C12 N11 H11A 110.(3) y
H11C N11 H11A 104.(4) y
H11B N11 H11A 104.(4) y
O12 C11 O11 125.9(3) y
O12 C11 C12 119.0(3) y
O11 C11 C12 115.1(3) y
N11 C12 C13 109.9(3) y
N11 C12 C11 108.2(3) y
C13 C12 C11 114.8(3) y
N11 C12 HC12 107.9(2) y
C13 C12 HC12 107.9(2) y
C11 C12 HC12 107.9(2) y
C12 C13 C14 113.6(3) y
C12 C13 H13A 108.8(2) y
C14 C13 H13A 108.8(2) y
C12 C13 H13B 108.8(2) y
C14 C13 H13B 108.8(2) y
H13A C13 H13B 107.7 y
C15 C14 C13 112.8(3) y
C15 C14 H14A 109.0(2) y
C13 C14 H14A 109.0(2) y
C15 C14 H14B 109.0(2) y
C13 C14 H14B 109.0(2) y
H14A C14 H14B 107.8 y
N16 C15 C14 110.4(3) y
N16 C15 H15A 109.6(2) y
C14 C15 H15A 109.6(2) y
N16 C15 H15B 109.6(2) y
C14 C15 H15B 109.6(2) y
H15A C15 H15B 108.1 y
C17 N16 C15 124.4(3) y
C17 N16 H16 117.8(2) y
C15 N16 H16 117.8(2) y
N16 C17 N19 118.9(3) y
N16 C17 N18 122.5(3) y
N19 C17 N18 118.6(3) y
C17 N18 H18A 120.0(2) y
C17 N18 H18B 120.0(2) y
H18A N18 H18B 120.0 y
C17 N19 H19A 120.0(2) y
C17 N19 H19B 120.0(2) y
H19A N19 H19B 120.0 y
C33 O32 H32 115.(3) y
O31 C33 O32 124.4(3) y
O31 C33 C34 120.7(3) y
O32 C33 C34 114.9(3) y
O35 C34 O36 127.6(3) y
O35 C34 C33 116.3(3) y
O36 C34 C33 116.1(3) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.477(4) y
N1 H1A 0.79(5) y
N1 H1B 0.96(4) y
N1 H1C 0.87(5) y
O2 C1 1.253(4) y
O1 C1 1.255(4) y
C1 C2 1.527(5) y
C2 C3 1.516(5) y
C2 HC2 0.98 y
C3 C4 1.529(5) y
C3 H3A 0.97 y
C3 H3B 0.97 y
C4 C5 1.527(5) y
C4 H4A 0.97 y
C4 H4B 0.97 y
C5 N6 1.454(5) y
C5 H5A 0.97 y
C5 H5B 0.97 y
N6 C7 1.321(4) y
N6 H6 0.86 y
C7 N8 1.320(4) y
C7 N9 1.330(4) y
N8 H8A 0.86 y
N8 H8B 0.86 y
N9 H9A 0.86 y
N9 H9B 0.86 y
O21 C23 1.201(4) y
O22 C23 1.305(4) y
O22 H22 0.82(5) y
C23 C24 1.549(5) y
C24 O25 1.236(4) y
C24 O26 1.248(4) y
N11 C12 1.495(4) y
N11 H11C 0.94(5) y
N11 H11B 0.94(5) y
N11 H11A 0.98(5) y
O11 C11 1.251(4) y
O12 C11 1.220(4) y
C11 C12 1.538(4) y
C12 C13 1.508(4) y
C12 HC12 0.98 y
C13 C14 1.529(5) y
C13 H13A 0.97 y
C13 H13B 0.97 y
C14 C15 1.514(4) y
C14 H14A 0.97 y
C14 H14B 0.97 y
C15 N16 1.455(5) y
C15 H15A 0.97 y
C15 H15B 0.97 y
N16 C17 1.312(4) y
N16 H16 0.86 y
C17 N19 1.314(5) y
C17 N18 1.323(4) y
N18 H18A 0.86 y
N18 H18B 0.86 y
N19 H19A 0.86 y
N19 H19B 0.86 y
O32 C33 1.293(4) y
O32 H32 0.92(5) y
O31 C33 1.218(4) y
C33 C34 1.547(5) y
C34 O35 1.241(4) y
C34 O36 1.239(4) y
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
_geom_torsion_publ_flag
O2 C1 C2 N1 179.6(3) y
O1 C1 C2 N1 1.5(4) y
O2 C1 C2 C3 -57.2(4) y
O1 C1 C2 C3 124.7(3) y
N1 C2 C3 C4 -64.0(4) y
C1 C2 C3 C4 173.7(3) y
C2 C3 C4 C5 176.8(3) y
C3 C4 C5 N6 50.1(4) y
C4 C5 N6 C7 99.4(4) y
C5 N6 C7 N8 -14.0(6) y
C5 N6 C7 N9 164.6(3) y
O21 C23 C24 O25 -10.0(5) y
O22 C23 C24 O25 169.7(3) y
O21 C23 C24 O26 170.3(3) y
O22 C23 C24 O26 -9.9(5) y
O12 C11 C12 N11 -152.8(3) y
O11 C11 C12 N11 27.6(4) y
O12 C11 C12 C13 -29.7(5) y
O11 C11 C12 C13 150.7(3) y
N11 C12 C13 C14 -76.2(4) y
C11 C12 C13 C14 161.7(3) y
C12 C13 C14 C15 165.1(3) y
C13 C14 C15 N16 55.2(4) y
C14 C15 N16 C17 -167.4(3) y
C15 N16 C17 N19 -174.2(4) y
C15 N16 C17 N18 6.1(6) y
O31 C33 C34 O35 7.7(5) y
O32 C33 C34 O35 -174.2(4) y
O31 C33 C34 O36 -172.0(4) y
O32 C33 C34 O36 6.0(5) y
