#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/83/2228379.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228379
loop_
_publ_author_name
'Gotoh, Kazuma'
'Maruyama, Shinpei'
'Ishida, Hiroyuki'
_publ_section_title
;
 Triethylammonium hydrogen chloranilate
;
_journal_coeditor_code           HG2739
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3255
_journal_paper_doi               10.1107/S1600536810047744
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H16 N +, C6 H Cl2 O4 -'
_chemical_formula_moiety         'C6 H16 N +, C6 H Cl2 O4 -'
_chemical_formula_sum            'C12 H17 Cl2 N O4'
_chemical_formula_weight         310.18
_chemical_name_common
;
Triethylammonium hydrogen chloranilate
;
_chemical_name_systematic
;
Triethylammonium 2,5-dichloro-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-olate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                99.9621(15)
_cell_angle_beta                 108.732(3)
_cell_angle_gamma                106.536(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6404(5)
_cell_length_b                   9.5352(3)
_cell_length_c                   11.2976(5)
_cell_measurement_reflns_used    12766
_cell_measurement_temperature    180.0(10)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.0
_cell_volume                     714.84(7)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_collection       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'CrystalStructure and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14757
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.462
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(NUMABS; Higashi, 1999)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324.00
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.355
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         4176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0543P)²+0.1133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0917
_reflns_number_gt                3631
_reflns_number_total             4176
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2739.cif
_cod_data_source_block           I
_cod_original_cell_volume        714.84(6)
_cod_original_formula_sum        'C12 H17 Cl2 N O4 '
_cod_database_code               2228379
_cod_database_fobs_code          2228379
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -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
Cl Cl1 0.05941(4) 0.44199(3) -0.17017(2) 0.03282(8) Uani d . 1 . .
Cl Cl2 0.79265(4) 0.85112(3) 0.35611(2) 0.03113(8) Uani d . 1 . .
O O1 0.23295(13) 0.35023(9) 0.06660(8) 0.03546(18) Uani d . 1 . .
O O2 0.29888(11) 0.77018(9) -0.10218(8) 0.02849(16) Uani d . 1 . .
O O3 0.60830(11) 0.93820(8) 0.11497(7) 0.02933(16) Uani d . 1 . .
O O4 0.53520(12) 0.51893(9) 0.29193(8) 0.03090(17) Uani d . 1 . .
N N1 0.31226(12) 0.21786(9) 0.28996(8) 0.02410(16) Uani d . 1 . .
C C1 0.31746(14) 0.48352(11) 0.07566(9) 0.02382(18) Uani d . 1 . .
C C2 0.25857(14) 0.55307(11) -0.02828(9) 0.02340(18) Uani d . 1 . .
C C3 0.35511(14) 0.70234(11) -0.01071(9) 0.02249(18) Uani d . 1 . .
C C4 0.53096(14) 0.80246(10) 0.11283(9) 0.02232(17) Uani d . 1 . .
C C5 0.59095(14) 0.73644(11) 0.21385(9) 0.02326(18) Uani d . 1 . .
C C6 0.49384(14) 0.58366(11) 0.20508(9) 0.02325(18) Uani d . 1 . .
C C7 0.12245(15) 0.22545(12) 0.29816(11) 0.0307(2) Uani d . 1 . .
H H7A 0.0632 0.1399 0.3289 0.037 Uiso calc R 1 . .
H H7B 0.0275 0.2125 0.2098 0.037 Uiso calc R 1 . .
C C8 0.15318(17) 0.37395(13) 0.38885(11) 0.0323(2) Uani d . 1 . .
H H8A 0.2209 0.3765 0.4795 0.048 Uiso calc R 1 . .
H H8B 0.0242 0.3827 0.3768 0.048 Uiso calc R 1 . .
H H8C 0.2344 0.4594 0.3693 0.048 Uiso calc R 1 . .
C C9 0.27183(18) 0.08580(12) 0.17789(11) 0.0320(2) Uani d . 1 . .
H H9A 0.3979 0.0937 0.1676 0.038 Uiso calc R 1 . .
H H9B 0.1802 0.0938 0.0967 0.038 Uiso calc R 1 . .
C C10 0.1828(2) -0.06935(13) 0.19402(15) 0.0435(3) Uani d . 1 . .
H H10A 0.2787 -0.0831 0.2686 0.065 Uiso calc R 1 . .
H H10B 0.1502 -0.1493 0.1145 0.065 Uiso calc R 1 . .
H H10C 0.0619 -0.0762 0.2094 0.065 Uiso calc R 1 . .
C C11 0.45590(16) 0.22080(13) 0.41806(11) 0.0313(2) Uani d . 1 . .
H H11A 0.3995 0.1271 0.4406 0.038 Uiso calc R 1 . .
H H11B 0.4747 0.3098 0.4872 0.038 Uiso calc R 1 . .
C C12 0.65531(19) 0.23066(17) 0.41462(15) 0.0461(3) Uani d . 1 . .
H H12A 0.6413 0.1348 0.3574 0.069 Uiso calc R 1 . .
H H12B 0.7501 0.2480 0.5031 0.069 Uiso calc R 1 . .
H H12C 0.7037 0.3156 0.3811 0.069 Uiso calc R 1 . .
H H1 0.365(2) 0.2974(19) 0.2713(14) 0.037(4) Uiso d . 1 . .
H H2 0.364(3) 0.855(2) -0.0717(17) 0.055(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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
C3 O2 H2 . . 106.0(13) ?
C11 N1 C9 . . 113.52(8) ?
C11 N1 C7 . . 111.98(8) ?
C9 N1 C7 . . 111.23(8) ?
C11 N1 H1 . . 107.6(10) ?
C9 N1 H1 . . 105.4(10) ?
C7 N1 H1 . . 106.5(10) ?
O1 C1 C2 . . 123.39(9) ?
O1 C1 C6 . . 118.01(8) ?
C2 C1 C6 . . 118.60(8) ?
C3 C2 C1 . . 120.43(9) ?
C3 C2 Cl1 . . 121.32(7) ?
C1 C2 Cl1 . . 118.21(7) ?
O2 C3 C2 . . 121.58(9) ?
O2 C3 C4 . . 115.99(8) ?
C2 C3 C4 . . 122.42(8) ?
O3 C4 C5 . . 126.59(9) ?
O3 C4 C3 . . 115.62(8) ?
C5 C4 C3 . . 117.79(8) ?
C6 C5 C4 . . 123.24(9) ?
C6 C5 Cl2 . . 118.80(7) ?
C4 C5 Cl2 . . 117.95(7) ?
O4 C6 C5 . . 126.67(9) ?
O4 C6 C1 . . 115.87(8) ?
C5 C6 C1 . . 117.46(8) ?
N1 C7 C8 . . 112.65(8) ?
N1 C7 H7A . . 109.1 ?
C8 C7 H7A . . 109.1 ?
N1 C7 H7B . . 109.1 ?
C8 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.8 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N1 C9 C10 . . 114.04(9) ?
N1 C9 H9A . . 108.7 ?
C10 C9 H9A . . 108.7 ?
N1 C9 H9B . . 108.7 ?
C10 C9 H9B . . 108.7 ?
H9A C9 H9B . . 107.6 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N1 C11 C12 . . 112.26(10) ?
N1 C11 H11A . . 109.2 ?
C12 C11 H11A . . 109.2 ?
N1 C11 H11B . . 109.2 ?
C12 C11 H11B . . 109.2 ?
H11A C11 H11B . . 107.9 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 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
Cl1 C2 . 1.7133(10) ?
Cl2 C5 . 1.7307(10) ?
O1 C1 . 1.2199(12) ?
O2 C3 . 1.3324(11) ?
O2 H2 . 0.766(18) ?
O3 C4 . 1.2529(11) ?
O4 C6 . 1.2510(11) ?
N1 C11 . 1.4993(13) ?
N1 C9 . 1.5033(13) ?
N1 C7 . 1.5036(13) ?
N1 H1 . 0.847(16) ?
C1 C2 . 1.4564(13) ?
C1 C6 . 1.5442(13) ?
C2 C3 . 1.3490(13) ?
C3 C4 . 1.5063(13) ?
C4 C5 . 1.4092(13) ?
C5 C6 . 1.4036(13) ?
C7 C8 . 1.5047(16) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C10 . 1.5115(16) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 C12 . 1.5130(16) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
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
N1 H1 O1 . 0.847(18) 2.411(15) 2.9805(12) 125.1(13)
N1 H1 O4 . 0.847(18) 2.069(18) 2.8833(12) 161.1(14)
O2 H2 O3 . 0.765(19) 2.147(19) 2.6331(11) 121.9(17)
O2 H2 O3 2_675 0.765(19) 2.082(19) 2.7089(12) 139.4(19)
C7 H7B O2 2_565 0.99 2.47 3.2859(15) 140
C8 H8A O4 2_666 0.98 2.47 3.3977(14) 158
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 178.24(10) ?
C6 C1 C2 C3 . . . . -0.79(14) ?
O1 C1 C2 Cl1 . . . . 0.38(14) ?
C6 C1 C2 Cl1 . . . . -178.65(7) ?
C1 C2 C3 O2 . . . . -177.16(9) ?
Cl1 C2 C3 O2 . . . . 0.63(14) ?
C1 C2 C3 C4 . . . . 2.41(15) ?
Cl1 C2 C3 C4 . . . . -179.80(7) ?
O2 C3 C4 O3 . . . . -1.57(12) ?
C2 C3 C4 O3 . . . . 178.84(9) ?
O2 C3 C4 C5 . . . . 177.84(8) ?
C2 C3 C4 C5 . . . . -1.75(14) ?
O3 C4 C5 C6 . . . . 178.64(9) ?
C3 C4 C5 C6 . . . . -0.70(14) ?
O3 C4 C5 Cl2 . . . . -0.55(14) ?
C3 C4 C5 Cl2 . . . . -179.88(7) ?
C4 C5 C6 O4 . . . . -177.80(10) ?
Cl2 C5 C6 O4 . . . . 1.38(15) ?
C4 C5 C6 C1 . . . . 2.18(14) ?
Cl2 C5 C6 C1 . . . . -178.64(6) ?
O1 C1 C6 O4 . . . . -0.58(14) ?
C2 C1 C6 O4 . . . . 178.50(9) ?
O1 C1 C6 C5 . . . . 179.44(9) ?
C2 C1 C6 C5 . . . . -1.48(13) ?
C11 N1 C7 C8 . . . . 64.50(11) ?
C9 N1 C7 C8 . . . . -167.30(9) ?
C11 N1 C9 C10 . . . . 60.54(13) ?
C7 N1 C9 C10 . . . . -66.83(13) ?
C9 N1 C11 C12 . . . . 59.27(12) ?
C7 N1 C11 C12 . . . . -173.75(9) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656362
