#------------------------------------------------------------------------------
#$Date: 2016-02-20 17:35:30 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/17/2211746.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_2211746
loop_
_publ_author_name
'Ejsmont, Krzysztof'
_publ_section_title
;
 Diethylammonium hydrogen oxalate
;
_journal_coeditor_code           BT2217
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o107
_journal_page_last               o109
_journal_paper_doi               10.1107/S1600536806051932
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C4 H12 N +, C2 H O4 -'
_chemical_formula_moiety         'C4 H12 N +, C2 H O4 -'
_chemical_formula_sum            'C6 H13 N O4'
_chemical_formula_weight         163.17
_chemical_name_systematic
;
Diethylammonium hydrogen oxalate
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 121.544(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.0527(4)
_cell_length_b                   5.5465(2)
_cell_length_c                   14.0317(6)
_cell_measurement_reflns_used    1850
_cell_measurement_temperature    298.0(10)
_cell_measurement_theta_max      29.33
_cell_measurement_theta_min      2.89
_cell_volume                     467.78(4)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298.0(10)
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0108
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2852
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.32
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             176
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     56
_refine_ls_number_reflns         872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0387
_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)+(0.0778P)²+0.1154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1165
_reflns_number_gt                744
_reflns_number_total             872
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2217.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               2211746
_cod_database_fobs_code          2211746
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
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
O O1 0.50394(19) 0.29848(16) 0.46517(8) 0.0576(4) Uani d . 1
H H1 0.5000 0.5000 0.5000 0.106(10) Uiso d S 1
O O2 0.5074(3) 0.14363(19) 0.61145(10) 0.0736(5) Uani d . 1
N N3 0.5000 0.2384(3) 0.2500 0.0494(5) Uani d S 1
H H3 0.496(3) 0.143(4) 0.3019(15) 0.071(6) Uiso d . 1
C C4 0.5041(2) 0.1255(2) 0.52430(11) 0.0432(4) Uani d . 1
C C5 0.7053(3) 0.3860(3) 0.30505(13) 0.0618(5) Uani d . 1
H H5A 0.7000 0.4970 0.3570 0.074 Uiso calc R 1
H H5B 0.7134 0.4802 0.2490 0.074 Uiso calc R 1
C C6 0.9072(4) 0.2332(7) 0.3662(2) 0.1203(11) Uani d . 1
H H6A 1.0371 0.3339 0.4008 0.180 Uiso calc R 1
H H6B 0.9142 0.1251 0.3147 0.180 Uiso calc R 1
H H6C 0.9008 0.1419 0.4226 0.180 Uiso calc R 1
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 0.1178(10) 0.0259(5) 0.0530(7) -0.0007(5) 0.0613(7) 0.0004(4)
O2 0.1623(13) 0.0342(6) 0.0578(7) -0.0012(6) 0.0809(8) -0.0029(5)
N3 0.0814(13) 0.0423(9) 0.0365(9) 0.000 0.0391(9) 0.000
C4 0.0745(10) 0.0283(7) 0.0385(7) 0.0001(6) 0.0377(7) -0.0001(5)
C5 0.0752(11) 0.0700(11) 0.0449(8) -0.0068(8) 0.0346(8) -0.0003(7)
C6 0.0873(18) 0.163(3) 0.1017(19) 0.0272(18) 0.0431(15) 0.0295(19)
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
C4 O1 H1 . . 114.90(10)
C5 N3 C5 . 2_655 112.89(19)
C5 N3 H3 . . 109.5(11)
C5 N3 H3 2_655 . 108.0(11)
O2 C4 O1 . . 126.07(11)
O2 C4 C4 . 3_656 119.88(14)
O1 C4 C4 . 3_656 114.05(12)
N3 C5 C6 . . 111.5(2)
N3 C5 H5A . . 109.3
C6 C5 H5A . . 109.3
N3 C5 H5B . . 109.3
C6 C5 H5B . . 109.3
H5A C5 H5B . . 108.0
C5 C6 H6A . . 109.5
C5 C6 H6B . . 109.5
H6A C6 H6B . . 109.5
C5 C6 H6C . . 109.5
H6A C6 H6C . . 109.5
H6B C6 H6C . . 109.5
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 . 1.268(2) y
O1 H1 . 1.230(10) ?
O2 C4 . 1.215(2) y
N3 C5 . 1.481(2) ?
N3 C5 2_655 1.481(2) ?
N3 H3 . 0.91(2) ?
C4 C4 3_656 1.538(2) ?
C5 C6 . 1.484(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
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 O1 3_666 1.230(10) 1.230(10) 2.4520(10) 179.98
N3 H3 O1 . 0.91(2) 2.42(2) 3.0231(9) 123(2)
N3 H3 O2 3_656 0.91(2) 2.01(2) 2.894(2) 163(2)
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_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N3 C5 C6 2_655 . . 175.9(2) y
O1 C4 C4 O1 . 3_656 3_656 180.0 ?
O2 C4 C4 O2 . 3_656 3_656 180.0 ?
