#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/97/2209744.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_2209744
loop_
_publ_author_name
'Ejsmont, Krzysztof'
'Zaleski, Jacek'
_publ_section_title
;
 Ethylammonium 2,4,5-tricarboxybenzoate
;
_journal_coeditor_code           BH2030
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3386
_journal_page_last               o3388
_journal_paper_doi               10.1107/S1600536806026948
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C2 H8 N +, C10 H5 O8 -'
_chemical_formula_moiety         'C2 H8 N +, C10 H5 O8 -'
_chemical_formula_sum            'C12 H13 N O8'
_chemical_formula_weight         299.23
_chemical_name_systematic
;
Ethylammonium 2,4,5-tricarboxybenzoate
;
_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
_cell_angle_alpha                94.830(4)
_cell_angle_beta                 94.467(5)
_cell_angle_gamma                110.874(6)
_cell_formula_units_Z            2
_cell_length_a                   7.4215(6)
_cell_length_b                   9.5775(6)
_cell_length_c                   9.7259(5)
_cell_measurement_reflns_used    4320
_cell_measurement_temperature    102.00(10)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      2.93
_cell_volume                     639.31(8)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2002)'
_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      102.00(10)
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       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  0.0076
_diffrn_reflns_av_sigmaI/netI    0.0101
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4320
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.93
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0282
_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)+(0.0495P)²+0.1846P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0851
_reflns_number_gt                2239
_reflns_number_total             2466
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2030.cif
_cod_data_source_block           I
_cod_database_code               2209744
_cod_database_fobs_code          2209744
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_occupancy
N N1 0.28288(15) 0.45808(12) 0.68171(10) 0.0151(2) Uani d 1
H H1A 0.179(3) 0.488(2) 0.6594(19) 0.043(5) Uiso d 1
H H1B 0.292(2) 0.3976(19) 0.6056(18) 0.029(4) Uiso d 1
H H1C 0.392(3) 0.540(2) 0.697(2) 0.042(5) Uiso d 1
C C2 0.2592(2) 0.37637(16) 0.80640(14) 0.0256(3) Uani d 1
H H2A 0.154(3) 0.285(2) 0.777(2) 0.049(5) Uiso d 1
H H2B 0.373(3) 0.358(2) 0.8233(19) 0.038(5) Uiso d 1
C C3 0.2235(3) 0.4694(2) 0.92620(15) 0.0352(4) Uani d 1
H H3A 0.115(3) 0.492(2) 0.9032(19) 0.043(5) Uiso d 1
H H3B 0.207(3) 0.418(2) 1.008(2) 0.048(5) Uiso d 1
H H3C 0.336(3) 0.564(3) 0.953(2) 0.062(6) Uiso d 1
C C4 0.24494(15) 0.08165(12) 0.32294(11) 0.0114(2) Uani d 1
C C5 0.26023(16) -0.01747(12) 0.21253(11) 0.0128(2) Uani d 1
C C6 0.26746(16) -0.15624(12) 0.24103(11) 0.0131(2) Uani d 1
H H6 0.279(2) -0.2232(17) 0.1645(16) 0.021(4) Uiso d 1
C C7 0.26450(15) -0.19756(12) 0.37423(11) 0.0111(2) Uani d 1
C C8 0.24714(15) -0.10018(12) 0.48338(11) 0.0111(2) Uani d 1
C C9 0.23464(15) 0.03612(12) 0.45537(12) 0.0115(2) Uani d 1
H H9 0.220(2) 0.1033(16) 0.5281(15) 0.015(3) Uiso d 1
C C10 0.24551(16) 0.23945(12) 0.31545(11) 0.0122(2) Uani d 1
O O11 0.16492(11) 0.28994(8) 0.40477(8) 0.01355(19) Uani d 1
O O12 0.33228(12) 0.31556(8) 0.22343(8) 0.0169(2) Uani d 1
C C13 0.26462(18) 0.00545(13) 0.06041(12) 0.0169(3) Uani d 1
O O14 0.31725(15) 0.14007(10) 0.02393(9) 0.0246(2) Uani d 1
H H14 0.337(3) 0.216(2) 0.106(2) 0.056(6) Uiso d 1
O O15 0.22121(15) -0.10506(10) -0.02651(9) 0.0259(2) Uani d 1
C C16 0.28627(16) -0.34529(12) 0.39428(11) 0.0116(2) Uani d 1
O O17 0.12065(11) -0.46092(9) 0.36604(8) 0.01529(19) Uani d 1
H H17 0.146(3) -0.548(2) 0.3751(19) 0.042(5) Uiso d 1
O O18 0.44153(11) -0.35509(9) 0.42550(9) 0.0172(2) Uani d 1
C C19 0.24535(15) -0.14075(12) 0.62876(11) 0.0118(2) Uani d 1
O O20 0.25604(12) -0.25905(9) 0.65714(8) 0.01620(19) Uani d 1
O O21 0.23426(12) -0.03547(9) 0.72002(8) 0.01591(19) Uani d 1
H H21 0.229(3) -0.064(2) 0.806(2) 0.042(5) Uiso 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
_geom_angle_publ_flag
C2 N1 H1A 112.1(11) ?
C2 N1 H1B 110.5(10) ?
H1A N1 H1B 107.7(15) ?
C2 N1 H1C 109.4(12) ?
H1A N1 H1C 108.8(16) ?
H1B N1 H1C 108.3(15) ?
N1 C2 C3 110.17(11) ?
N1 C2 H2A 104.2(12) ?
C3 C2 H2A 113.5(12) ?
N1 C2 H2B 105.3(11) ?
C3 C2 H2B 112.9(11) ?
H2A C2 H2B 110.0(16) ?
C2 C3 H3A 110.5(12) ?
C2 C3 H3B 111.3(12) ?
H3A C3 H3B 109.2(16) ?
C2 C3 H3C 110.9(13) ?
H3A C3 H3C 108.8(18) ?
H3B C3 H3C 105.9(17) ?
C9 C4 C5 118.57(10) ?
C9 C4 C10 114.56(9) y
C5 C4 C10 126.83(10) y
C6 C5 C4 118.64(10) ?
C6 C5 C13 113.77(10) y
C4 C5 C13 127.57(10) y
C7 C6 C5 122.11(10) ?
C7 C6 H6 119.9(9) ?
C5 C6 H6 118.0(9) ?
C6 C7 C8 119.26(10) ?
C6 C7 C16 117.55(9) ?
C8 C7 C16 123.17(9) ?
C9 C8 C7 118.99(10) ?
C9 C8 C19 120.39(10) ?
C7 C8 C19 120.61(9) ?
C8 C9 C4 122.36(10) ?
C8 C9 H9 120.3(8) ?
C4 C9 H9 117.4(8) ?
O11 C10 O12 123.20(10) y
O11 C10 C4 117.47(9) y
O12 C10 C4 119.33(9) y
C10 O12 H14 109.8(8) ?
O15 C13 O14 121.00(10) y
O15 C13 C5 118.80(10) y
O14 C13 C5 120.20(10) y
C13 O14 H14 110.7(11) ?
O18 C16 O17 124.50(10) y
O18 C16 C7 122.70(10) y
O17 C16 C7 112.69(9) y
C16 O17 H17 108.0(11) ?
O20 C19 O21 124.60(10) y
O20 C19 C8 122.20(10) y
O21 C19 C8 113.22(9) y
C19 O21 H21 111.7(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.486(2) ?
N1 H1A 0.931(19) ?
N1 H1B 0.923(18) ?
N1 H1C 0.90(2) ?
C2 C3 1.504(2) ?
C2 H2A 0.95(2) ?
C2 H2B 0.929(18) ?
C3 H3A 0.92(2) ?
C3 H3B 0.96(2) ?
C3 H3C 0.99(2) ?
C4 C9 1.393(2) ?
C4 C5 1.411(2) ?
C4 C10 1.5180(10) ?
C5 C6 1.399(2) ?
C5 C13 1.515(2) ?
C6 C7 1.386(2) ?
C6 H6 0.970(15) ?
C7 C8 1.398(2) ?
C7 C16 1.5070(10) ?
C8 C9 1.389(2) ?
C8 C19 1.4974(15) ?
C9 H9 0.955(15) ?
C10 O11 1.2500(10) ?
C10 O12 1.2700(10) ?
C13 O15 1.226(2) y
C13 O14 1.2960(10) y
O14 H14 1.00(2) ?
C16 O18 1.2067(15) y
C16 O17 1.3190(10) y
O17 H17 0.932(19) ?
C19 O20 1.2160(10) y
C19 O21 1.3160(10) y
O21 H21 0.90(2) ?
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
_geom_hbond_publ_flag
O14 H14 O12 . 1.00(2) 1.44(2) 2.4260(10) 171(2) yes
C6 H6 O15 . 0.97(2) 2.34(2) 2.7060(10) 101.0(10) yes
C9 H9 O11 . 0.96(2) 2.370(10) 2.7350(10) 102.0(10) yes
C9 H9 O21 . 0.96(2) 2.400(10) 2.7190(10) 99.2(9) yes
N1 H1B O11 . 0.92(2) 2.11(2) 2.9180(10) 146.0(10) yes
N1 H1A O17 2_556 0.93(2) 2.14(2) 3.0050(10) 155(2) yes
N1 H1A O20 1_565 0.93(2) 2.29(2) 2.8150(10) 115.0(10) yes
N1 H1B O18 2_656 0.92(3) 2.19(2) 2.8000(10) 123.0(10) yes
N1 H1C O12 2_666 0.90(2) 2.06(2) 2.9240(10) 161(2) yes
O17 H17 O11 1_545 0.93(2) 1.65(2) 2.5760(10) 172(2) yes
O21 H21 O15 1_556 0.90(2) 1.71(2) 2.6080(10) 176(2) yes
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
C9 C4 C5 C6 -0.98(16) ?
C10 C4 C5 C6 176.61(10) ?
C9 C4 C5 C13 177.15(11) ?
C10 C4 C5 C13 -5.25(18) ?
C4 C5 C6 C7 -1.49(17) ?
C13 C5 C6 C7 -179.87(10) ?
C5 C6 C7 C8 2.21(17) ?
C5 C6 C7 C16 -176.05(10) ?
C6 C7 C8 C9 -0.44(16) ?
C16 C7 C8 C9 177.73(10) ?
C6 C7 C8 C19 -179.43(10) ?
C16 C7 C8 C19 -1.26(16) ?
C7 C8 C9 C4 -2.08(16) ?
C19 C8 C9 C4 176.91(10) ?
C5 C4 C9 C8 2.79(16) ?
C10 C4 C9 C8 -175.10(11) ?
C9 C4 C10 O11 -27.00(10) y
C5 C4 C10 O11 155.30(10) y
C9 C4 C10 O12 150.60(10) y
C5 C4 C10 O12 -27.1(2) y
C6 C5 C13 O15 19.6(2) y
C4 C5 C13 O15 -158.70(10) y
C6 C5 C13 O14 -159.10(10) y
C4 C5 C13 O14 22.7(2) y
C6 C7 C16 O18 92.50(10) y
C8 C7 C16 O18 -85.70(10) y
C6 C7 C16 O17 -83.70(10) y
C8 C7 C16 O17 98.10(10) y
C9 C8 C19 O20 180.00(10) y
C7 C8 C19 O20 -1.0(2) y
C9 C8 C19 O21 -1.00(10) y
C7 C8 C19 O21 178.00(9) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127828
