#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/75/2017584.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_2017584
loop_
_publ_author_name
'Martinez Belmonte, Marta'
'Price, Daniel J.'
_publ_section_title
;
 Strong asymmetric hydrogen bonding in 2-(oxamoylamino)ethylammonium
 oxamate--oxamic acid (1/1)
;
_journal_coeditor_code           TR3064
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o147
_journal_page_last               o150
_journal_paper_doi               10.1107/S0108270110004233
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C4 H10 N3 O2 + , C2 H2 N O3 - , C2 H3 N O3'
_chemical_formula_moiety         'C4 H10 N3 O2 + , C2 H3 N O3 - , C2 H2 N O3'
_chemical_formula_sum            'C8 H15 N5 O8'
_chemical_formula_weight         309.25
_chemical_name_common
'N-(ethylammonium)oxamide hydrogen bis(oxamate)'
_chemical_name_systematic
;
2-(oxamoylamino)ethylammonium oxamate--oxamic acid (1/1)
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                97.765(2)
_cell_angle_beta                 97.304(2)
_cell_angle_gamma                102.394(2)
_cell_formula_units_Z            2
_cell_length_a                   5.1723(2)
_cell_length_b                   10.3560(4)
_cell_length_c                   12.1866(5)
_cell_measurement_reflns_used    768
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      1.71
_cell_volume                     623.43(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SAINT (Bruker, 1997)'
_computing_data_reduction        'SMART (Bruker, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008) and WinGX (Farrugia, 1999)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13083
_diffrn_reflns_theta_full        30.55
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.238
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0399
_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)+(0.0561P)²+0.0433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                2895
_reflns_number_total             3812
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tr3064.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2017584
_cod_database_fobs_code          2017584
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
N N1 0.2608(2) 0.72976(12) 0.45733(10) 0.0209(3) Uani d . 1 . .
H H1A 0.313(3) 0.7663(16) 0.5326(15) 0.025 Uiso d . 1 . .
H H1B 0.121(4) 0.6674(17) 0.4383(15) 0.025 Uiso d . 1 . .
C C1 0.4053(2) 0.77512(12) 0.38268(10) 0.0136(2) Uani d . 1 . .
O O1 0.61092(19) 0.86607(9) 0.40618(8) 0.0200(2) Uani d . 1 . .
C C2 0.2994(2) 0.70454(12) 0.26115(10) 0.0124(2) Uani d . 1 . .
O O2 0.09733(18) 0.61105(9) 0.23891(8) 0.01561(19) Uani d . 1 . .
N N2 0.4447(2) 0.75179(11) 0.18648(9) 0.0135(2) Uani d . 1 . .
H H2 0.582(3) 0.8130(15) 0.2119(13) 0.016 Uiso d . 1 . .
C C3 0.3995(2) 0.68371(13) 0.06999(10) 0.0148(2) Uani d . 1 . .
H H3D 0.4098 0.5913 0.0699 0.018 Uiso calc R 1 . .
H H3E 0.5433 0.7257 0.0333 0.018 Uiso calc R 1 . .
C C4 0.1346(2) 0.68464(12) 0.00155(10) 0.0147(2) Uani d . 1 . .
H H4C 0.1078 0.6234 -0.0687 0.018 Uiso calc R 1 . .
H H4D -0.0094 0.6523 0.0420 0.018 Uiso calc R 1 . .
N N3 0.1192(2) 0.82033(11) -0.02295(9) 0.0153(2) Uani d . 1 . .
H H3C 0.253(3) 0.8556(15) -0.0567(14) 0.018 Uiso d . 1 . .
H H3A 0.122(3) 0.8772(15) 0.0409(14) 0.018 Uiso d . 1 . .
H H3B -0.032(3) 0.8127(15) -0.0727(14) 0.018 Uiso d . 1 . .
N N4 0.8935(2) 0.98516(11) 0.63823(9) 0.0164(2) Uani d . 1 . .
H H4A 0.762(3) 0.9358(16) 0.5854(14) 0.020 Uiso d . 1 . .
H H4B 1.043(3) 1.0304(15) 0.6198(13) 0.020 Uiso d . 1 . .
C C5 0.8681(2) 0.99644(12) 0.74536(10) 0.0123(2) Uani d . 1 . .
O O3 1.04099(18) 1.06597(9) 0.82274(8) 0.01670(19) Uani d . 1 . .
C C6 0.6007(2) 0.91625(12) 0.77285(10) 0.0125(2) Uani d . 1 . .
O O4 0.57424(18) 0.92886(9) 0.87283(8) 0.0169(2) Uani d . 1 . .
O O5 0.43537(17) 0.84384(9) 0.68968(7) 0.01457(19) Uani d . 1 . .
N N5 -0.6253(2) 0.50466(11) 0.66850(9) 0.0146(2) Uani d . 1 . .
H H5A -0.765(3) 0.4711(15) 0.6960(14) 0.017 Uiso d . 1 . .
H H5B -0.632(3) 0.4842(15) 0.5946(14) 0.017 Uiso d . 1 . .
C C7 -0.4199(2) 0.59075(12) 0.73629(10) 0.0120(2) Uani d . 1 . .
O O6 -0.40840(18) 0.62595(9) 0.83769(7) 0.01561(19) Uani d . 1 . .
C C8 -0.1838(2) 0.64464(12) 0.67667(10) 0.0117(2) Uani d . 1 . .
O O7 0.00814(18) 0.72967(9) 0.74660(8) 0.01465(19) Uani d . 1 . .
H H7 0.160(4) 0.7713(19) 0.7159(17) 0.048(6) Uiso d . 1 . .
O O8 -0.18686(18) 0.60920(9) 0.57703(7) 0.0167(2) 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 0.0016 '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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 H1A . . 119.9(11) n
C1 N1 H1B . . 121.5(12) n
H1A N1 H1B . . 118.6(16) n
O1 C1 N1 . . 124.06(12) y
O1 C1 C2 . . 121.19(11) y
N1 C1 C2 . . 114.75(11) y
O2 C2 N2 . . 125.02(12) y
O2 C2 C1 . . 120.66(10) y
N2 C2 C1 . . 114.31(11) y
C2 N2 C3 . . 121.79(11) y
C2 N2 H2 . . 116.5(11) n
C3 N2 H2 . . 120.6(11) n
N2 C3 C4 . . 115.14(10) y
N2 C3 H3D . . 108.5 n
C4 C3 H3D . . 108.5 n
N2 C3 H3E . . 108.5 n
C4 C3 H3E . . 108.5 n
H3D C3 H3E . . 107.5 n
N3 C4 C3 . . 113.03(10) y
N3 C4 H4C . . 109.0 n
C3 C4 H4C . . 109.0 n
N3 C4 H4D . . 109.0 n
C3 C4 H4D . . 109.0 n
H4C C4 H4D . . 107.8 n
C4 N3 H3C . . 112.0(10) n
C4 N3 H3A . . 111.0(9) n
H3C N3 H3A . . 108.7(14) n
C4 N3 H3B . . 109.1(9) n
H3C N3 H3B . . 105.0(14) n
H3A N3 H3B . . 110.9(14) n
C5 N4 H4A . . 121.1(11) n
C5 N4 H4B . . 118.4(11) n
H4A N4 H4B . . 120.4(15) n
O3 C5 N4 . . 124.30(11) y
O3 C5 C6 . . 119.40(11) y
N4 C5 C6 . . 116.30(11) y
O4 C6 O5 . . 127.52(11) y
O4 C6 C5 . . 116.40(11) y
O5 C6 C5 . . 116.07(10) y
C7 N5 H5A . . 118.9(11) n
C7 N5 H5B . . 123.6(10) n
H5A N5 H5B . . 117.3(15) n
O6 C7 N5 . . 125.47(11) y
O6 C7 C8 . . 120.73(11) y
N5 C7 C8 . . 113.80(11) y
O8 C8 O7 . . 126.90(11) y
O8 C8 C7 . . 122.18(11) y
O7 C8 C7 . . 110.93(10) y
C8 O7 H7 . . 116.6(12) n
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
N1 C1 . 1.3208(15) y
N1 H1A . 0.926(18) n
N1 H1B . 0.841(19) n
C1 O1 . 1.2330(15) y
C1 C2 . 1.5353(17) y
C2 O2 . 1.2353(15) y
C2 N2 . 1.3297(15) y
N2 C3 . 1.4634(16) y
N2 H2 . 0.838(16) n
C3 C4 . 1.5135(17) y
C3 H3D . 0.9700 n
C3 H3E . 0.9700 n
C4 N3 . 1.4918(16) y
C4 H4C . 0.9700 n
C4 H4D . 0.9700 n
N3 H3C . 0.887(16) n
N3 H3A . 0.907(17) n
N3 H3B . 0.908(17) n
N4 C5 . 1.3207(16) y
N4 H4A . 0.888(17) n
N4 H4B . 0.888(17) n
C5 O3 . 1.2381(15) y
C5 C6 . 1.5542(17) y
C6 O4 . 1.2358(15) y
C6 O5 . 1.2726(15) y
N5 C7 . 1.3331(16) y
N5 H5A . 0.860(17) n
N5 H5B . 0.891(16) n
C7 O6 . 1.2303(15) y
C7 C8 . 1.5406(16) y
C8 O8 . 1.2172(15) y
C8 O7 . 1.3015(15) y
O7 H7 . 0.96(2) n
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
O7 H7 O5 . 0.96(2) 1.55(2) 2.5004(12) 169.0(19)
N1 H1A O5 . 0.926(18) 1.941(18) 2.8665(15) 178.0(16)
N1 H1B O8 . 0.841(19) 2.513(17) 3.0261(14) 120.3(15)
N2 H2 O3 2_776 0.838(16) 2.202(16) 2.9377(14) 146.6(14)
N3 H3C O4 1_554 0.887(16) 2.018(17) 2.9027(14) 175.8(15)
N3 H3A O3 2_676 0.907(17) 2.029(17) 2.8606(14) 151.7(14)
N3 H3A O4 2_676 0.907(17) 2.295(16) 2.9695(15) 130.9(13)
N3 H3B O7 1_554 0.908(17) 2.305(16) 2.7828(14) 112.6(12)
N3 H3B O6 1_554 0.908(17) 2.449(17) 3.1502(15) 134.2(12)
N3 H3B O4 1_454 0.908(17) 2.639(16) 3.4143(15) 143.9(13)
N4 H4A O1 . 0.888(17) 2.191(17) 2.9811(15) 148.0(14)
N4 H4B O1 2_776 0.888(17) 1.964(17) 2.8497(14) 174.7(15)
N5 H5A O2 2_466 0.860(17) 2.052(17) 2.9122(14) 179.4(16)
N5 H5B O8 2_466 0.891(16) 2.181(17) 3.0172(15) 156.2(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654228
