#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/10/2201043.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_2201043
loop_
_publ_author_name
'Ohba, Shigeru'
'Ito, Yoshikatsu'
_publ_section_title
;
 2-(3,4-Dimethoxyphenyl)ethylammonium 3,5-dinitrobenzoate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o588
_journal_page_last               o589
_journal_paper_doi               10.1107/S1600536802007304
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C10 H16 N O2 1+, C7 H3 N2 O6 1-'
_chemical_formula_moiety         'C10 H16 N O2 1+, C7 H3 N2 O6 1-'
_chemical_formula_sum            'C17 H19 N3 O8'
_chemical_formula_weight         393.35
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                106.451(10)
_cell_angle_beta                 101.240(9)
_cell_angle_gamma                94.890(8)
_cell_formula_units_Z            2
_cell_length_a                   10.0546(9)
_cell_length_b                   10.9344(13)
_cell_length_c                   9.0112(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    250.0(10)
_cell_measurement_theta_max      29.4
_cell_measurement_theta_min      25.2
_cell_volume                     921.5(2)
_computing_cell_refinement       'WinAFC Diffractometer Control Software'
_computing_data_collection
'WinAFC Diffractometer Control Software (Rigaku, 1999)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1999)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_device_type  'Rigaku AFC-7R'
_diffrn_measurement_method       θ-2θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4022
_diffrn_reflns_theta_full        65
_diffrn_reflns_theta_max         75.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.978
_exptl_absorpt_correction_T_max  0.741
_exptl_absorpt_correction_T_min  0.582
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Coppens et al., 1965)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.25
_refine_ls_extinction_coef       0.0042(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.11
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3362
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.0606P)²+0.3459P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.125
_reflns_number_gt                3229
_reflns_number_total             3362
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6143.cif
_cod_data_source_block           I
_cod_database_code               2201043
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.46230(10) 0.80370(10) 0.46840(10) 0.0435(3) Uani d . 1.00 . . O
O2 0.25620(10) 0.83070(10) 0.26820(10) 0.0489(3) Uani d . 1.00 . . O
O3 -0.22690(10) 0.46230(10) 0.02370(10) 0.0562(4) Uani d . 1.00 . . O
O4 -0.30430(10) 0.5755(2) 0.2288(2) 0.0663(4) Uani d . 1.00 . . O
O5 0.0273(2) 0.8190(2) 0.7185(2) 0.0721(4) Uani d . 1.00 . . O
O6 0.2259(2) 0.7610(2) 0.7702(2) 0.0637(4) Uani d . 1.00 . . O
O7 0.38850(10) 0.4924(2) 0.3193(2) 0.0641(4) Uani d . 1.00 . . O
O8 0.2317(2) 0.3369(2) 0.1685(2) 0.0702(4) Uani d . 1.00 . . O
N9 0.52570(10) 1.31390(10) 0.8672(2) 0.0420(3) Uani d . 1.00 . . N
N10 0.1160(2) 0.75540(10) 0.6806(2) 0.0462(4) Uani d . 1.00 . . N
N11 0.2688(2) 0.4435(2) 0.2643(2) 0.0470(4) Uani d . 1.00 . . N
C12 0.5666(2) 0.7712(2) 0.5762(2) 0.0499(4) Uani d . 1.00 . . C
C13 0.1408(2) 0.8378(2) 0.1529(2) 0.0627(6) Uani d . 1.00 . . C
C14 0.4144(2) 0.9718(2) 0.6864(2) 0.0404(4) Uani d . 1.00 . . C
C15 0.3864(2) 0.89550(10) 0.5301(2) 0.0356(3) Uani d . 1.00 . . C
C16 0.2725(2) 0.9086(2) 0.4207(2) 0.0378(3) Uani d . 1.00 . . C
C17 0.1878(2) 0.9965(2) 0.4723(2) 0.0445(4) Uani d . 1.00 . . C
C18 0.2181(2) 1.0732(2) 0.6301(2) 0.0463(4) Uani d . 1.00 . . C
C19 0.3305(2) 1.0631(2) 0.7383(2) 0.0424(4) Uani d . 1.00 . . C
C20 0.3617(2) 1.1486(2) 0.9092(2) 0.0553(5) Uani d . 1.00 . . C
C21 0.5020(2) 1.2319(2) 0.9674(2) 0.0509(4) Uani d . 1.00 . . C
C22 -0.2133(2) 0.5296(2) 0.1642(2) 0.0412(4) Uani d . 1.00 . . C
C23 -0.0695(2) 0.55690(10) 0.2705(2) 0.0346(3) Uani d . 1.00 . . C
C24 -0.0415(2) 0.6436(2) 0.4225(2) 0.0362(3) Uani d . 1.00 . . C
C25 0.0887(2) 0.66510(10) 0.5181(2) 0.0364(3) Uani d . 1.00 . . C
C26 0.1936(2) 0.6023(2) 0.4697(2) 0.0387(4) Uani d . 1.00 . . C
C27 0.1618(2) 0.5163(2) 0.3185(2) 0.0369(3) Uani d . 1.00 . . C
C28 0.0335(2) 0.4923(2) 0.2173(2) 0.0362(3) Uani d . 1.00 . . C
H9A 0.449(2) 1.366(2) 0.849(2) 0.06064(7) Uiso d . 1.00 . . H
H9B 0.538(2) 1.269(2) 0.774(2) 0.04285(6) Uiso d . 1.00 . . H
H9C 0.612(2) 1.372(2) 0.918(3) 0.06175(8) Uiso d . 1.00 . . H
H12A 0.6342 0.8446 0.6309 0.0599 Uiso calc . 1.00 . . H
H12B 0.5272 0.7433 0.6511 0.0599 Uiso calc . 1.00 . . H
H12C 0.6080 0.7037 0.5191 0.0599 Uiso calc . 1.00 . . H
H13A 0.1454 0.9225 0.1447 0.0755 Uiso calc . 1.00 . . H
H13B 0.1399 0.7781 0.0530 0.0755 Uiso calc . 1.00 . . H
H13C 0.0589 0.8170 0.1849 0.0755 Uiso calc . 1.00 . . H
H14 0.4915 0.9622 0.7598 0.0484 Uiso calc . 1.00 . . H
H17 0.1090 1.0047 0.4000 0.0534 Uiso calc . 1.00 . . H
H18 0.1597 1.1340 0.6641 0.0555 Uiso calc . 1.00 . . H
H20A 0.2941 1.2042 0.9195 0.0664 Uiso calc . 1.00 . . H
H20B 0.3561 1.0950 0.9749 0.0664 Uiso calc . 1.00 . . H
H21A 0.5094 1.2858 1.0727 0.0611 Uiso calc . 1.00 . . H
H21B 0.5704 1.1769 0.9674 0.0611 Uiso calc . 1.00 . . H
H24 -0.1114 0.6879 0.4604 0.0434 Uiso calc . 1.00 . . H
H26 0.2827 0.6177 0.5369 0.0464 Uiso calc . 1.00 . . H
H28 0.0162 0.4327 0.1134 0.0433 Uiso calc . 1.00 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C)
;
N N 0.031 0.018
;International Tables for Crystallography
(1992, Vol. C)
;
O O 0.049 0.032
;International Tables for Crystallography
(1992, Vol. C)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O1 C15 1_555 1_555 118.00(10) no
C13 O2 C16 1_555 1_555 117.70(10) no
C21 N9 H9A 1_555 1_555 113.0(10) no
C21 N9 H9B 1_555 1_555 112(2) no
C21 N9 H9C 1_555 1_555 109(2) no
H9A N9 H9B 1_555 1_555 108(2) no
H9A N9 H9C 1_555 1_555 109(2) no
H9B N9 H9C 1_555 1_555 105(2) no
O5 N10 O6 1_555 1_555 123.70(10) yes
O5 N10 C25 1_555 1_555 118.30(10) no
O6 N10 C25 1_555 1_555 117.90(10) no
O7 N11 O8 1_555 1_555 124.1(2) yes
O7 N11 C27 1_555 1_555 118.50(10) no
O8 N11 C27 1_555 1_555 117.40(10) no
O1 C12 H12A 1_555 1_555 109.6 no
O1 C12 H12B 1_555 1_555 109.5 no
O1 C12 H12C 1_555 1_555 109.6 no
H12A C12 H12B 1_555 1_555 109.3 no
H12A C12 H12C 1_555 1_555 109.4 no
H12B C12 H12C 1_555 1_555 109.3 no
O2 C13 H13A 1_555 1_555 109.7 no
O2 C13 H13B 1_555 1_555 109.6 no
O2 C13 H13C 1_555 1_555 109.2 no
H13A C13 H13B 1_555 1_555 109.8 no
H13A C13 H13C 1_555 1_555 109.3 no
H13B C13 H13C 1_555 1_555 109.2 no
C15 C14 C19 1_555 1_555 120.80(10) no
C15 C14 H14 1_555 1_555 119.6 no
C19 C14 H14 1_555 1_555 119.6 no
O1 C15 C14 1_555 1_555 125.00(10) no
O1 C15 C16 1_555 1_555 115.00(10) no
C14 C15 C16 1_555 1_555 120.1(2) no
O2 C16 C15 1_555 1_555 115.30(10) no
O2 C16 C17 1_555 1_555 125.40(10) no
C15 C16 C17 1_555 1_555 119.30(10) no
C16 C17 C18 1_555 1_555 119.8(2) no
C16 C17 H17 1_555 1_555 120.1 no
C18 C17 H17 1_555 1_555 120.1 no
C17 C18 C19 1_555 1_555 121.6(2) no
C17 C18 H18 1_555 1_555 119.1 no
C19 C18 H18 1_555 1_555 119.2 no
C14 C19 C18 1_555 1_555 118.40(10) no
C14 C19 C20 1_555 1_555 121.2(2) no
C18 C19 C20 1_555 1_555 120.5(2) no
C19 C20 C21 1_555 1_555 115.0(2) no
C19 C20 H20A 1_555 1_555 108.0 no
C19 C20 H20B 1_555 1_555 108.1 no
C21 C20 H20A 1_555 1_555 108.1 no
C21 C20 H20B 1_555 1_555 108.1 no
H20A C20 H20B 1_555 1_555 109.5 no
N9 C21 C20 1_555 1_555 112.90(10) no
N9 C21 H21A 1_555 1_555 108.6 no
N9 C21 H21B 1_555 1_555 108.6 no
C20 C21 H21A 1_555 1_555 108.6 no
C20 C21 H21B 1_555 1_555 108.6 no
H21A C21 H21B 1_555 1_555 109.4 no
O3 C22 O4 1_555 1_555 127.40(10) yes
O3 C22 C23 1_555 1_555 116.50(10) no
O4 C22 C23 1_555 1_555 116.10(10) no
C22 C23 C24 1_555 1_555 120.30(10) no
C22 C23 C28 1_555 1_555 120.20(10) no
C24 C23 C28 1_555 1_555 119.60(10) no
C23 C24 C25 1_555 1_555 119.40(10) no
C23 C24 H24 1_555 1_555 120.3 no
C25 C24 H24 1_555 1_555 120.3 no
N10 C25 C24 1_555 1_555 118.80(10) no
N10 C25 C26 1_555 1_555 118.50(10) no
C24 C25 C26 1_555 1_555 122.70(10) no
C25 C26 C27 1_555 1_555 116.30(10) no
C25 C26 H26 1_555 1_555 121.9 no
C27 C26 H26 1_555 1_555 121.9 no
N11 C27 C26 1_555 1_555 118.10(10) no
N11 C27 C28 1_555 1_555 118.50(10) no
C26 C27 C28 1_555 1_555 123.3(2) no
C23 C28 C27 1_555 1_555 118.70(10) no
C23 C28 H28 1_555 1_555 120.7 no
C27 C28 H28 1_555 1_555 120.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C12 . . 1.426(2) no
O1 C15 . . 1.370(2) no
O2 C13 . . 1.422(2) no
O2 C16 . . 1.367(2) no
O3 C22 . . 1.245(2) yes
O4 C22 . . 1.243(2) yes
O5 N10 . . 1.219(2) yes
O6 N10 . . 1.220(2) yes
O7 N11 . . 1.220(2) yes
O8 N11 . . 1.214(2) yes
N9 C21 . . 1.478(3) no
N9 H9A . . 1.01(2) no
N9 H9B . . 0.88(2) no
N9 H9C . . 0.97(2) no
N10 C25 . . 1.474(2) no
N11 C27 . . 1.469(2) no
C12 H12A . . 0.950 no
C12 H12B . . 0.951 no
C12 H12C . . 0.951 no
C13 H13A . . 0.948 no
C13 H13B . . 0.948 no
C13 H13C . . 0.954 no
C14 C15 . . 1.378(2) no
C14 C19 . . 1.400(3) no
C14 H14 . . 0.950 no
C15 C16 . . 1.404(2) no
C16 C17 . . 1.381(3) no
C17 C18 . . 1.389(2) no
C17 H17 . . 0.950 no
C18 C19 . . 1.376(3) no
C18 H18 . . 0.950 no
C19 C20 . . 1.513(2) no
C20 C21 . . 1.522(3) no
C20 H20A . . 0.950 no
C20 H20B . . 0.950 no
C21 H21A . . 0.950 no
C21 H21B . . 0.951 no
C22 C23 . . 1.524(2) no
C23 C24 . . 1.387(2) no
C23 C28 . . 1.388(2) no
C24 C25 . . 1.380(2) no
C24 H24 . . 0.950 no
C25 C26 . . 1.381(2) no
C26 C27 . . 1.377(2) no
C26 H26 . . 0.951 no
C27 C28 . . 1.384(2) no
C28 H28 . . 0.951 no
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
N9 H9A O4 2_576 1.01(2) 1.74(2) 2.733(2) 165(2)
N9 H9B O1 2_676 0.88(2) 2.10(2) 2.963(2) 164(2)
N9 H9B O2 2_676 0.88(2) 2.47(2) 3.056(2) 125(2)
N9 H9C O3 1_666 0.97(2) 1.76(2) 2.731(2) 172(2)
