#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/10/2201041.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_2201041
loop_
_publ_author_name
'Ohba, Shigeru'
'Ito, Yoshikatsu'
_publ_section_title
;
 2-(4-Hydroxyphenyl)ethylammonium picrate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o584
_journal_page_last               o585
_journal_paper_doi               10.1107/S1600536802007286
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C8 H12 N O 1+, C6 H2 N3 O7 1-'
_chemical_formula_moiety         'C8 H12 N O 1+, C6 H2 N3 O7 1-'
_chemical_formula_sum            'C14 H14 N4 O8'
_chemical_formula_weight         366.29
_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                104.391(6)
_cell_angle_beta                 96.502(6)
_cell_angle_gamma                83.654(6)
_cell_formula_units_Z            2
_cell_length_a                   8.9692(6)
_cell_length_b                   12.3120(10)
_cell_length_c                   7.3832(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    250.0(10)
_cell_measurement_theta_max      29.6
_cell_measurement_theta_min      25.4
_cell_volume                     781.77(11)
_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 0.948
_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  0.047
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3422
_diffrn_reflns_theta_full        65
_diffrn_reflns_theta_max         75.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.127
_exptl_absorpt_correction_T_max  0.809
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Coppens et al., 1965)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.24
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3050
_refine_ls_R_factor_gt           0.049
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.0858P)²+0.2511P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.143
_reflns_number_gt                2939
_reflns_number_total             3050
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6141.cif
_cod_data_source_block           I
_cod_original_cell_volume        781.80(10)
_cod_database_code               2201041
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 0.91680(10) 1.31090(10) 0.5128(2) 0.0544(4) Uani d . 1.00 . . O
O2 0.37290(10) 0.89420(9) 0.2564(2) 0.0409(3) Uani d . 1.00 . . O
O3 0.6149(2) 0.79370(10) 0.0780(2) 0.0586(4) Uani d . 1.00 . . O
O4 0.6160(2) 0.61380(10) -0.0171(3) 0.0743(5) Uani d . 1.00 . . O
O5 0.1662(2) 0.46090(10) -0.3155(2) 0.0674(4) Uani d . 1.00 . . O
O6 -0.0469(2) 0.53040(10) -0.2084(2) 0.0627(4) Uani d . 1.00 . . O
O7 -0.0798(9) 0.8950(10) 0.195(2) 0.077(3) Uani d P 0.50 . . O
O8 0.0967(3) 1.0013(2) 0.2337(7) 0.0770(10) Uani d P 0.50 . . O
O9 -0.0950(10) 0.9054(10) 0.1590(10) 0.068(2) Uani d P 0.50 . . O
O10 0.0857(4) 0.9643(3) 0.3591(6) 0.0740(10) Uani d P 0.50 . . O
N11 0.3180(2) 1.08480(10) 0.5540(2) 0.0380(3) Uani d . 1.00 . . N
N12 0.5501(2) 0.70710(10) 0.0343(2) 0.0443(4) Uani d . 1.00 . . N
N13 0.0895(2) 0.53340(10) -0.2113(2) 0.0473(4) Uani d . 1.00 . . N
N14 0.0451(2) 0.90350(10) 0.2023(2) 0.0535(4) Uani d . 1.00 . . N
C15 0.5876(2) 1.16170(10) 0.3102(2) 0.0423(4) Uani d . 1.00 . . C
C16 0.7369(2) 1.18650(10) 0.3571(2) 0.0420(4) Uani d . 1.00 . . C
C17 0.7689(2) 1.28920(10) 0.4755(2) 0.0398(4) Uani d . 1.00 . . C
C18 0.6534(2) 1.36600(10) 0.5497(2) 0.0427(4) Uani d . 1.00 . . C
C19 0.5052(2) 1.33960(10) 0.5029(3) 0.0446(4) Uani d . 1.00 . . C
C20 0.4701(2) 1.23730(10) 0.3827(2) 0.0415(4) Uani d . 1.00 . . C
C21 0.3076(2) 1.2105(2) 0.3360(3) 0.0512(4) Uani d . 1.00 . . C
C22 0.2384(2) 1.18640(10) 0.4982(3) 0.0437(4) Uani d . 1.00 . . C
C23 0.3080(2) 0.81500(10) 0.1459(2) 0.0348(3) Uani d . 1.00 . . C
C24 0.3867(2) 0.71520(10) 0.0351(2) 0.0359(3) Uani d . 1.00 . . C
C25 0.3173(2) 0.62500(10) -0.0759(2) 0.0390(4) Uani d . 1.00 . . C
C26 0.1617(2) 0.62700(10) -0.0888(2) 0.0393(4) Uani d . 1.00 . . C
C27 0.0751(2) 0.71860(10) 0.0055(2) 0.0389(4) Uani d . 1.00 . . C
C28 0.1455(2) 0.80960(10) 0.1154(2) 0.0375(4) Uani d . 1.00 . . C
H1 0.914(4) 1.371(3) 0.579(5) 0.10520(10) Uiso d . 1.00 . . H
H11A 0.410(3) 1.099(2) 0.608(3) 0.06100(8) Uiso d . 1.00 . . H
H11B 0.320(2) 1.025(2) 0.454(3) 0.04512(6) Uiso d . 1.00 . . H
H11C 0.263(2) 1.069(2) 0.642(3) 0.04951(7) Uiso d . 1.00 . . H
H15 0.5658 1.0919 0.2271 0.0507 Uiso calc . 1.00 . . H
H16 0.8162 1.1333 0.3082 0.0503 Uiso calc . 1.00 . . H
H18 0.6755 1.4361 0.6318 0.0512 Uiso calc . 1.00 . . H
H19 0.4262 1.3922 0.5539 0.0535 Uiso calc . 1.00 . . H
H21A 0.2506 1.2730 0.3008 0.0613 Uiso calc . 1.00 . . H
H21B 0.3028 1.1463 0.2336 0.0613 Uiso calc . 1.00 . . H
H22A 0.2453 1.2495 0.6024 0.0525 Uiso calc . 1.00 . . H
H22B 0.1356 1.1738 0.4617 0.0525 Uiso calc . 1.00 . . H
H25 0.3753 0.5616 -0.1434 0.0467 Uiso calc . 1.00 . . H
H27 -0.0316 0.7191 -0.0052 0.0466 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
C17 O1 H1 1_555 1_555 103(3) no
C22 N11 H11A 1_555 1_555 110(2) no
C22 N11 H11B 1_555 1_555 110.0(10) no
C22 N11 H11C 1_555 1_555 107.0(10) no
H11A N11 H11B 1_555 1_555 112(2) no
H11A N11 H11C 1_555 1_555 108(2) no
H11B N11 H11C 1_555 1_555 108(2) no
O3 N12 O4 1_555 1_555 122.8(2) no
O3 N12 C24 1_555 1_555 118.90(10) no
O4 N12 C24 1_555 1_555 118.20(10) no
O5 N13 O6 1_555 1_555 122.80(10) no
O5 N13 C26 1_555 1_555 118.6(2) no
O6 N13 C26 1_555 1_555 118.60(10) no
O7 N14 O8 1_555 1_555 121.1(6) no
O7 N14 C28 1_555 1_555 120.4(6) no
O8 N14 C28 1_555 1_555 115.1(2) no
O9 N14 O10 1_555 1_555 115.6(5) no
O9 N14 C28 1_555 1_555 121.0(5) no
O10 N14 C28 1_555 1_555 119.5(2) no
C16 C15 C20 1_555 1_555 121.20(10) no
C16 C15 H15 1_555 1_555 119.4 no
C20 C15 H15 1_555 1_555 119.4 no
C15 C16 C17 1_555 1_555 119.50(10) no
C15 C16 H16 1_555 1_555 120.2 no
C17 C16 H16 1_555 1_555 120.2 no
O1 C17 C16 1_555 1_555 117.30(10) no
O1 C17 C18 1_555 1_555 122.40(10) no
C16 C17 C18 1_555 1_555 120.3(2) no
C17 C18 C19 1_555 1_555 119.40(10) no
C17 C18 H18 1_555 1_555 120.3 no
C19 C18 H18 1_555 1_555 120.3 no
C18 C19 C20 1_555 1_555 121.30(10) no
C18 C19 H19 1_555 1_555 119.3 no
C20 C19 H19 1_555 1_555 119.3 no
C15 C20 C19 1_555 1_555 118.2(2) no
C15 C20 C21 1_555 1_555 121.70(10) no
C19 C20 C21 1_555 1_555 120.10(10) no
C20 C21 C22 1_555 1_555 113.3(2) no
C20 C21 H21A 1_555 1_555 108.5 no
C20 C21 H21B 1_555 1_555 108.5 no
C22 C21 H21A 1_555 1_555 108.5 no
C22 C21 H21B 1_555 1_555 108.5 no
H21A C21 H21B 1_555 1_555 109.5 no
N11 C22 C21 1_555 1_555 111.20(10) no
N11 C22 H22A 1_555 1_555 109.0 no
N11 C22 H22B 1_555 1_555 109.0 no
C21 C22 H22A 1_555 1_555 109.0 no
C21 C22 H22B 1_555 1_555 109.0 no
H22A C22 H22B 1_555 1_555 109.5 no
O2 C23 C24 1_555 1_555 124.00(10) no
O2 C23 C28 1_555 1_555 124.70(10) no
C24 C23 C28 1_555 1_555 111.30(10) no
N12 C24 C23 1_555 1_555 120.30(10) no
N12 C24 C25 1_555 1_555 115.30(10) no
C23 C24 C25 1_555 1_555 124.40(10) no
C24 C25 C26 1_555 1_555 119.40(10) no
C24 C25 H25 1_555 1_555 120.3 no
C26 C25 H25 1_555 1_555 120.3 no
N13 C26 C25 1_555 1_555 118.90(10) no
N13 C26 C27 1_555 1_555 119.60(10) no
C25 C26 C27 1_555 1_555 121.40(10) no
C26 C27 C28 1_555 1_555 119.00(10) no
C26 C27 H27 1_555 1_555 120.5 no
C28 C27 H27 1_555 1_555 120.5 no
N14 C28 C23 1_555 1_555 120.60(10) no
N14 C28 C27 1_555 1_555 114.90(10) no
C23 C28 C27 1_555 1_555 124.50(10) 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 C17 . . 1.366(2) yes
O1 H1 . . 0.78(3) no
O2 C23 . . 1.256(2) yes
O3 N12 . . 1.226(2) no
O4 N12 . . 1.223(2) no
O5 N13 . . 1.227(2) no
O6 N13 . . 1.231(2) no
O7 N14 . . 1.131(8) no
O8 N14 . . 1.296(4) no
O9 N14 . . 1.259(9) no
O10 N14 . . 1.252(4) no
N11 C22 . . 1.495(2) no
N11 H11A . . 0.89(2) no
N11 H11B . . 0.90(2) no
N11 H11C . . 0.93(3) no
N12 C24 . . 1.458(2) no
N13 C26 . . 1.442(2) no
N14 C28 . . 1.445(2) no
C15 C16 . . 1.392(3) no
C15 C20 . . 1.388(2) no
C15 H15 . . 0.950 no
C16 C17 . . 1.386(2) no
C16 H16 . . 0.950 no
C17 C18 . . 1.386(2) no
C18 C19 . . 1.388(3) no
C18 H18 . . 0.950 no
C19 C20 . . 1.393(2) no
C19 H19 . . 0.950 no
C20 C21 . . 1.513(3) no
C21 C22 . . 1.514(3) no
C21 H21A . . 0.950 no
C21 H21B . . 0.950 no
C22 H22A . . 0.950 no
C22 H22B . . 0.950 no
C23 C24 . . 1.455(2) no
C23 C28 . . 1.456(2) no
C24 C25 . . 1.371(2) no
C25 C26 . . 1.386(2) no
C25 H25 . . 0.950 no
C26 C27 . . 1.378(2) no
C27 C28 . . 1.379(2) no
C27 H27 . . 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 O5 1_666 0.78(3) 2.59(4) 3.022(2) 117(2)
O1 H1 O6 1_666 0.78(3) 2.22(3) 2.988(2) 168(3)
N11 H11B O2 . 0.90(2) 1.94(2) 2.829(2) 167(2)
N11 H11A O2 2_676 0.89(2) 2.08(2) 2.969(2) 170(2)
N11 H11A O3 2_676 0.89(2) 2.39(2) 2.791(2) 108(2)
N11 H11C O7 2_576 0.93(3) 2.09(2) 2.930(10) 151(2)
N11 H11B O8 . 0.90(2) 2.42(2) 2.961(4) 118(2)
N11 H11C O9 2_576 0.93(3) 2.16(3) 3.050(10) 158(2)
N11 H11B O10 . 0.90(2) 2.28(2) 2.748(4) 112(2)
