#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/10/2201042.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_2201042
loop_
_publ_author_name
'Ohba, Shigeru'
'Ito, Yoshikatsu'
_publ_section_title
;
 2-(3,4-Dihydroxyphenyl)ethylammonium 3,5-dinitrobenzoate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o586
_journal_page_last               o587
_journal_paper_doi               10.1107/S1600536802007298
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C8 H12 N O2 1+, C7 H3 N2 O6 1-'
_chemical_formula_moiety         'C8 H12 N O2 1+, C7 H3 N2 O6 1-'
_chemical_formula_sum            'C15 H15 N3 O8'
_chemical_formula_weight         365.30
_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                103.233(6)
_cell_angle_beta                 97.756(7)
_cell_angle_gamma                113.585(8)
_cell_formula_units_Z            2
_cell_length_a                   11.3920(10)
_cell_length_b                   11.6440(10)
_cell_length_c                   6.7552(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    250.0(10)
_cell_measurement_theta_max      29.0
_cell_measurement_theta_min      25.4
_cell_volume                     773.21(12)
_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 0.947
_diffrn_measurement_device_type  'Rigaku AFC-7R'
_diffrn_measurement_method       θ-2θ
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.076
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3648
_diffrn_reflns_theta_full        60
_diffrn_reflns_theta_max         75.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        3.0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.118
_exptl_absorpt_correction_T_max  0.903
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Coppens et al., 1965)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3025
_refine_ls_R_factor_gt           0.037
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.0614P)²+0.2307P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.118
_reflns_number_gt                2625
_reflns_number_total             3025
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6142.cif
_cod_data_source_block           I
_cod_original_cell_volume        773.20(10)
_cod_database_code               2201042
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 -0.30800(10) 0.19600(10) 0.1593(2) 0.0449(3) Uani d . 1.00 . . O
O2 -0.04910(10) 0.27880(10) 0.2166(2) 0.0410(3) Uani d . 1.00 . . O
O3 0.39860(10) 0.58840(10) 0.3146(2) 0.0410(3) Uani d . 1.00 . . O
O4 0.20380(10) 0.41290(10) 0.2281(2) 0.0448(3) Uani d . 1.00 . . O
O5 -0.18960(10) 0.48870(10) 0.2509(3) 0.0584(4) Uani d . 1.00 . . O
O6 -0.16810(10) 0.68690(10) 0.3573(2) 0.0511(3) Uani d . 1.00 . . O
O7 0.23290(10) 1.04690(10) 0.3650(2) 0.0459(3) Uani d . 1.00 . . O
O8 0.41120(10) 1.02340(10) 0.3615(2) 0.0482(3) Uani d . 1.00 . . O
N9 -0.39030(10) -0.31530(10) -0.3327(2) 0.0375(3) Uani d . 1.00 . . N
N10 -0.12400(10) 0.60820(10) 0.3012(2) 0.0388(3) Uani d . 1.00 . . N
N11 0.29340(10) 0.97970(10) 0.3535(2) 0.0339(3) Uani d . 1.00 . . N
C12 -0.34390(10) -0.0251(2) 0.1123(2) 0.0333(3) Uani d . 1.00 . . C
C13 -0.25890(10) 0.1059(2) 0.1500(2) 0.0313(3) Uani d . 1.00 . . C
C14 -0.12280(10) 0.14730(10) 0.1793(2) 0.0310(3) Uani d . 1.00 . . C
C15 -0.0734(2) 0.0566(2) 0.1741(3) 0.0363(3) Uani d . 1.00 . . C
C16 -0.1601(2) -0.0761(2) 0.1312(3) 0.0374(4) Uani d . 1.00 . . C
C17 -0.2952(2) -0.1184(2) 0.0994(2) 0.0332(3) Uani d . 1.00 . . C
C18 -0.3895(2) -0.2632(2) 0.0454(3) 0.0421(4) Uani d . 1.00 . . C
C19 -0.4733(2) -0.3237(2) -0.1795(3) 0.0423(4) Uani d . 1.00 . . C
C20 0.2764(2) 0.5354(2) 0.2743(2) 0.0319(3) Uani d . 1.00 . . C
C21 0.20770(10) 0.62460(10) 0.2835(2) 0.0300(3) Uani d . 1.00 . . C
C22 0.0737(2) 0.57560(10) 0.2740(2) 0.0321(3) Uani d . 1.00 . . C
C23 0.01610(10) 0.6606(2) 0.2970(2) 0.0315(3) Uani d . 1.00 . . C
C24 0.0852(2) 0.79330(10) 0.3241(2) 0.0314(3) Uani d . 1.00 . . C
C25 0.2176(2) 0.83850(10) 0.3265(2) 0.0301(3) Uani d . 1.00 . . C
C26 0.28140(10) 0.75890(10) 0.3106(2) 0.0304(3) Uani d . 1.00 . . C
H1 -0.237(3) 0.279(3) 0.193(4) 0.08830(10) Uiso d . 1.00 . . H
H2 0.034(3) 0.306(3) 0.214(4) 0.07530(10) Uiso d . 1.00 . . H
H9A -0.337(2) -0.228(2) -0.322(3) 0.05061(7) Uiso d . 1.00 . . H
H9B -0.335(2) -0.355(2) -0.312(3) 0.04893(7) Uiso d . 1.00 . . H
H9C -0.448(2) -0.359(2) -0.466(3) 0.04571(7) Uiso d . 1.00 . . H
H12 -0.4361 -0.0520 0.0951 0.0399 Uiso calc . 1.00 . . H
H15 0.0193 0.0843 0.1997 0.0435 Uiso calc . 1.00 . . H
H16 -0.1258 -0.1387 0.1237 0.0449 Uiso calc . 1.00 . . H
H18A -0.4468 -0.2723 0.1369 0.0506 Uiso calc . 1.00 . . H
H18B -0.3392 -0.3096 0.0665 0.0506 Uiso calc . 1.00 . . H
H19A -0.5307 -0.4137 -0.2020 0.0508 Uiso calc . 1.00 . . H
H19B -0.5244 -0.2781 -0.2013 0.0508 Uiso calc . 1.00 . . H
H22 0.0217 0.4843 0.2519 0.0385 Uiso calc . 1.00 . . H
H24 0.0441 0.8504 0.3402 0.0376 Uiso calc . 1.00 . . H
H26 0.3735 0.7946 0.3178 0.0365 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
C13 O1 H1 1_555 1_555 108(2) no
C14 O2 H2 1_555 1_555 117(2) no
C19 N9 H9A 1_555 1_555 111(2) no
C19 N9 H9B 1_555 1_555 112.0(10) no
C19 N9 H9C 1_555 1_555 107.0(10) no
H9A N9 H9B 1_555 1_555 108(2) no
H9A N9 H9C 1_555 1_555 110(2) no
H9B N9 H9C 1_555 1_555 110(2) no
O5 N10 O6 1_555 1_555 123.60(10) yes
O5 N10 C23 1_555 1_555 118.3(2) no
O6 N10 C23 1_555 1_555 118.10(10) no
O7 N11 O8 1_555 1_555 123.70(10) yes
O7 N11 C25 1_555 1_555 117.50(10) no
O8 N11 C25 1_555 1_555 118.9(2) no
C13 C12 C17 1_555 1_555 120.40(10) no
C13 C12 H12 1_555 1_555 119.8 no
C17 C12 H12 1_555 1_555 119.8 no
O1 C13 C12 1_555 1_555 119.80(10) no
O1 C13 C14 1_555 1_555 119.70(10) no
C12 C13 C14 1_555 1_555 120.5(2) no
O2 C14 C13 1_555 1_555 115.1(2) no
O2 C14 C15 1_555 1_555 125.40(10) no
C13 C14 C15 1_555 1_555 119.50(10) no
C14 C15 C16 1_555 1_555 119.7(2) no
C14 C15 H15 1_555 1_555 120.2 no
C16 C15 H15 1_555 1_555 120.1 no
C15 C16 C17 1_555 1_555 121.2(2) no
C15 C16 H16 1_555 1_555 119.4 no
C17 C16 H16 1_555 1_555 119.4 no
C12 C17 C16 1_555 1_555 118.60(10) no
C12 C17 C18 1_555 1_555 120.20(10) no
C16 C17 C18 1_555 1_555 121.1(2) no
C17 C18 C19 1_555 1_555 113.3(2) no
C17 C18 H18A 1_555 1_555 108.5 no
C17 C18 H18B 1_555 1_555 108.5 no
C19 C18 H18A 1_555 1_555 108.5 no
C19 C18 H18B 1_555 1_555 108.5 no
H18A C18 H18B 1_555 1_555 109.5 no
N9 C19 C18 1_555 1_555 111.70(10) no
N9 C19 H19A 1_555 1_555 108.9 no
N9 C19 H19B 1_555 1_555 108.9 no
C18 C19 H19A 1_555 1_555 108.9 no
C18 C19 H19B 1_555 1_555 108.9 no
H19A C19 H19B 1_555 1_555 109.5 no
O3 C20 O4 1_555 1_555 125.0(2) yes
O3 C20 C21 1_555 1_555 117.60(10) no
O4 C20 C21 1_555 1_555 117.40(10) no
C20 C21 C22 1_555 1_555 120.90(10) no
C20 C21 C26 1_555 1_555 119.90(10) no
C22 C21 C26 1_555 1_555 119.2(2) no
C21 C22 C23 1_555 1_555 119.50(10) no
C21 C22 H22 1_555 1_555 120.3 no
C23 C22 H22 1_555 1_555 120.2 no
N10 C23 C22 1_555 1_555 118.50(10) no
N10 C23 C24 1_555 1_555 118.4(2) no
C22 C23 C24 1_555 1_555 123.00(10) no
C23 C24 C25 1_555 1_555 116.2(2) no
C23 C24 H24 1_555 1_555 121.9 no
C25 C24 H24 1_555 1_555 121.9 no
N11 C25 C24 1_555 1_555 117.2(2) no
N11 C25 C26 1_555 1_555 119.40(10) no
C24 C25 C26 1_555 1_555 123.30(10) no
C21 C26 C25 1_555 1_555 118.70(10) no
C21 C26 H26 1_555 1_555 120.7 no
C25 C26 H26 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 C13 . . 1.366(3) no
O1 H1 . . 0.93(3) no
O2 C14 . . 1.360(2) no
O2 H2 . . 0.88(3) no
O3 C20 . . 1.236(2) yes
O4 C20 . . 1.264(2) yes
O5 N10 . . 1.222(2) yes
O6 N10 . . 1.223(2) yes
O7 N11 . . 1.230(2) yes
O8 N11 . . 1.218(2) yes
N9 C19 . . 1.487(3) no
N9 H9A . . 0.93(2) no
N9 H9B . . 0.93(3) no
N9 H9C . . 0.93(2) no
N10 C23 . . 1.470(2) no
N11 C25 . . 1.472(2) no
C12 C13 . . 1.380(2) no
C12 C17 . . 1.396(3) no
C12 H12 . . 0.950 no
C13 C14 . . 1.396(2) no
C14 C15 . . 1.378(3) no
C15 C16 . . 1.394(2) no
C15 H15 . . 0.950 no
C16 C17 . . 1.383(2) no
C16 H16 . . 0.950 no
C17 C18 . . 1.514(2) no
C18 C19 . . 1.515(3) no
C18 H18A . . 0.950 no
C18 H18B . . 0.950 no
C19 H19A . . 0.950 no
C19 H19B . . 0.950 no
C20 C21 . . 1.526(3) no
C21 C22 . . 1.386(2) no
C21 C26 . . 1.401(2) no
C22 C23 . . 1.382(3) no
C22 H22 . . 0.950 no
C23 C24 . . 1.378(2) no
C24 C25 . . 1.380(2) no
C24 H24 . . 0.950 no
C25 C26 . . 1.384(3) no
C26 H26 . . 0.950 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
O1 H1 O2 . 0.93(3) 2.13(4) 2.650(2) 114(3)
O1 H1 O5 . 0.93(3) 2.20(3) 2.991(2) 142(3)
O2 H2 O4 . 0.88(3) 1.81(3) 2.652(2) 161(3)
N9 H9C O3 1_444 0.93(2) 1.91(2) 2.791(2) 157(2)
N9 H9B O4 2_555 0.93(3) 1.94(3) 2.863(2) 171(2)
N9 H9A O7 2_565 0.93(2) 2.08(2) 2.994(2) 168(2)
