#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/19/2201988.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_2201988
loop_
_publ_author_name
'Yu, Qing'
'Tang, Yu'
'Feng, Yan-Hua'
'Tan, Min-Yu'
'Yu, Kai-Bei'
_publ_section_title
;
 N---H···O hydrogen bonding in the adduct of
 N-(2-aminoethyl)-2-hydroxybenzamide with picric acid
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o577
_journal_page_last               o578
_journal_paper_doi               10.1107/S160053680300655X
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C15 H15 N5 O9'
_chemical_formula_moiety         'C15 H15 N5 O9'
_chemical_formula_sum            'C15 H15 N5 O9'
_chemical_formula_weight         409.32
_chemical_name_systematic
;
N-(2-aminoethyl)-2-hydroxybenzamide picrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.84(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.761(3)
_cell_length_b                   8.005(2)
_cell_length_c                   17.744(6)
_cell_measurement_reflns_used    27
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      13.19
_cell_measurement_theta_min      3.02
_cell_volume                     1791.1(9)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'SHELXTL (Bruker, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3305
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        2.78
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.227
_refine_ls_extinction_coef       0.0056(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0516
_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)+(0.074P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1421
_reflns_number_gt                1801
_reflns_number_total             3154
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl6023.cif
_cod_data_source_block           I
_cod_original_cell_volume        1790.9(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2201988
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.8080(2) -0.0748(3) 0.51533(13) 0.0763(7) Uani d . 1 . . O
H1 0.8005 -0.0641 0.5602 0.092 Uiso calc R 1 . . H
O2 0.71836(17) 0.0335(3) 0.62923(11) 0.0572(6) Uani d . 1 . . O
N1 0.5678(2) 0.1805(3) 0.60658(13) 0.0510(7) Uani d . 1 . . N
H1N 0.5228 0.2311 0.5732 0.061 Uiso calc R 1 . . H
N2 0.7215(2) 0.2678(3) 0.76478(12) 0.0522(7) Uani d . 1 . . N
H2A 0.7193 0.1723 0.7902 0.063 Uiso calc R 1 . . H
H2B 0.7517 0.3465 0.7963 0.063 Uiso calc R 1 . . H
H2C 0.7591 0.2534 0.7270 0.063 Uiso calc R 1 . . H
C1 0.7334(3) 0.0136(4) 0.47126(17) 0.0529(8) Uani d . 1 . . C
C2 0.7383(3) 0.0134(4) 0.39318(19) 0.0675(10) Uani d . 1 . . C
H2 0.7895 -0.0501 0.3743 0.081 Uiso calc R 1 . . H
C3 0.6682(3) 0.1062(5) 0.34464(19) 0.0707(10) Uani d . 1 . . C
H3 0.6725 0.1071 0.2928 0.085 Uiso calc R 1 . . H
C4 0.5914(3) 0.1980(5) 0.37166(18) 0.0689(10) Uani d . 1 . . C
H4 0.5445 0.2622 0.3382 0.083 Uiso calc R 1 . . H
C5 0.5833(3) 0.1959(4) 0.44750(16) 0.0560(8) Uani d . 1 . . C
H5 0.5300 0.2571 0.4650 0.067 Uiso calc R 1 . . H
C6 0.6546(2) 0.1026(3) 0.49972(14) 0.0419(7) Uani d . 1 . . C
C7 0.6480(2) 0.1033(3) 0.58249(15) 0.0416(7) Uani d . 1 . . C
C8 0.5506(2) 0.1855(4) 0.68561(16) 0.0563(8) Uani d . 1 . . C
H8A 0.5698 0.0779 0.7089 0.068 Uiso calc R 1 . . H
H8B 0.4756 0.2025 0.6867 0.068 Uiso calc R 1 . . H
C9 0.6122(3) 0.3197(4) 0.73289(17) 0.0582(9) Uani d . 1 . . C
H9A 0.6155 0.4182 0.7015 0.070 Uiso calc R 1 . . H
H9B 0.5746 0.3499 0.7745 0.070 Uiso calc R 1 . . H
O3 0.69062(17) -0.0284(2) 0.84008(10) 0.0532(6) Uani d . 1 . . O
O4 0.8397(2) 0.1505(4) 0.92114(14) 0.0921(9) Uani d . 1 . . O
O5 0.8655(2) 0.1248(3) 1.04270(14) 0.0809(8) Uani d . 1 . . O
O6 0.6136(3) -0.1328(4) 1.17567(14) 0.1018(10) Uani d . 1 . . O
O7 0.4992(3) -0.2975(5) 1.11658(15) 0.1290(14) Uani d . 1 . . O
O8 0.4262(2) -0.2668(4) 0.83869(14) 0.0969(10) Uani d . 1 . . O
O9 0.5702(2) -0.2983(3) 0.79256(13) 0.0733(7) Uani d . 1 . . O
N3 0.8138(2) 0.0951(3) 0.98020(16) 0.0571(7) Uani d . 1 . . N
N4 0.5694(3) -0.1959(4) 1.11798(17) 0.0727(9) Uani d . 1 . . N
N5 0.5229(2) -0.2530(3) 0.84301(14) 0.0557(7) Uani d . 1 . . N
C10 0.6675(2) -0.0667(3) 0.90373(14) 0.0397(7) Uani d . 1 . . C
C11 0.7197(2) -0.0069(3) 0.97670(15) 0.0415(7) Uani d . 1 . . C
C12 0.6879(2) -0.0472(4) 1.04454(15) 0.0482(8) Uani d . 1 . . C
H12 0.7242 -0.0044 1.0899 0.058 Uiso calc R 1 . . H
C13 0.6025(2) -0.1510(4) 1.04568(15) 0.0484(8) Uani d . 1 . . C
C14 0.5481(2) -0.2175(4) 0.97948(16) 0.0497(8) Uani d . 1 . . C
H14 0.4905 -0.2881 0.9807 0.060 Uiso calc R 1 . . H
C15 0.5807(2) -0.1771(3) 0.91208(14) 0.0423(7) Uani d . 1 . . C
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
C1 O1 H1 109.5
C7 N1 C8 124.4(3)
C7 N1 H1N 117.8
C8 N1 H1N 117.8
C9 N2 H2A 109.5
C9 N2 H2B 109.5
H2A N2 H2B 109.5
C9 N2 H2C 109.5
H2A N2 H2C 109.5
H2B N2 H2C 109.5
O1 C1 C6 123.3(3)
O1 C1 C2 116.3(3)
C6 C1 C2 120.4(3)
C3 C2 C1 120.1(3)
C3 C2 H2 120.0
C1 C2 H2 120.0
C2 C3 C4 120.5(3)
C2 C3 H3 119.8
C4 C3 H3 119.8
C5 C4 C3 120.3(3)
C5 C4 H4 119.9
C3 C4 H4 119.9
C4 C5 C6 121.1(3)
C4 C5 H5 119.4
C6 C5 H5 119.4
C1 C6 C5 117.6(3)
C1 C6 C7 121.1(3)
C5 C6 C7 121.3(3)
O2 C7 N1 120.3(3)
O2 C7 C6 120.6(3)
N1 C7 C6 119.1(3)
N1 C8 C9 114.4(2)
N1 C8 H8A 108.7
C9 C8 H8A 108.7
N1 C8 H8B 108.7
C9 C8 H8B 108.7
H8A C8 H8B 107.6
N2 C9 C8 113.1(3)
N2 C9 H9A 109.0
C8 C9 H9A 109.0
N2 C9 H9B 109.0
C8 C9 H9B 109.0
H9A C9 H9B 107.8
O5 N3 O4 121.7(3)
O5 N3 C11 118.5(3)
O4 N3 C11 119.8(3)
O6 N4 O7 123.4(3)
O6 N4 C13 119.0(3)
O7 N4 C13 117.6(3)
O9 N5 O8 122.5(3)
O9 N5 C15 120.0(3)
O8 N5 C15 117.5(3)
O3 C10 C15 122.4(2)
O3 C10 C11 126.1(3)
C15 C10 C11 111.5(2)
C12 C11 C10 123.6(3)
C12 C11 N3 116.9(3)
C10 C11 N3 119.4(2)
C11 C12 C13 120.0(3)
C11 C12 H12 120.0
C13 C12 H12 120.0
C12 C13 C14 121.2(3)
C12 C13 N4 120.0(3)
C14 C13 N4 118.7(3)
C15 C14 C13 118.4(3)
C15 C14 H14 120.8
C13 C14 H14 120.8
C14 C15 C10 125.3(3)
C14 C15 N5 117.0(3)
C10 C15 N5 117.7(2)
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
O1 C1 . 1.337(4) ?
O1 H1 . 0.8200 ?
O2 C7 . 1.256(3) ?
N1 C7 . 1.321(4) ?
N1 C8 . 1.453(3) ?
N1 H1N . 0.8600 ?
N2 C9 . 1.482(4) ?
N2 H2A . 0.8900 ?
N2 H2B . 0.8900 ?
N2 H2C . 0.8900 ?
C1 C6 . 1.390(4) ?
C1 C2 . 1.397(4) ?
C2 C3 . 1.363(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.370(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.365(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.409(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.484(4) ?
C8 C9 . 1.508(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
O3 C10 . 1.249(3) ?
O4 N3 . 1.229(3) ?
O5 N3 . 1.223(3) ?
O6 N4 . 1.201(4) ?
O7 N4 . 1.207(4) ?
O8 N5 . 1.229(3) ?
O9 N5 . 1.209(3) ?
N3 C11 . 1.446(4) ?
N4 C13 . 1.456(4) ?
N5 C15 . 1.462(4) ?
C10 C15 . 1.442(4) ?
C10 C11 . 1.444(4) ?
C11 C12 . 1.366(4) ?
C12 C13 . 1.374(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.376(4) ?
C14 C15 . 1.364(4) ?
C14 H14 . 0.9300 ?
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
O1 H1 O2 . 0.82 1.90 2.618(3) 146 y
N2 H2B O2 2_656 0.89 1.99 2.865(3) 165 y
N2 H2A O3 . 0.89 1.90 2.779(3) 171 y
N1 H1N O5 4_565 0.86 2.31 3.078(8) 150 y
N2 H2A O4 . 0.89 2.59 3.093(2) 117 y
N2 H2C O2 . 0.89 2.47 3.045(4) 123 y
N2 H2C O3 2_656 0.89 2.26 2.832(4) 122 y
N2 H2C O9 2_656 0.89 2.30 3.0350(10) 141 y
C2 H2 O8 4_655 0.93 2.44 3.360(6) 174 y
C4 H4 O9 3_656 0.93 2.56 3.397(2) 150 ?
C5 H5 O4 4_565 0.93 2.54 3.308(6) 140 ?
C9 H9B O7 3_657 0.97 2.31 3.217(7) 154 y
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
O1 C1 C2 C3 -177.1(3)
C6 C1 C2 C3 2.6(5)
C1 C2 C3 C4 -1.0(6)
C2 C3 C4 C5 -0.9(6)
C3 C4 C5 C6 1.3(5)
O1 C1 C6 C5 177.5(3)
C2 C1 C6 C5 -2.2(4)
O1 C1 C6 C7 -0.5(5)
C2 C1 C6 C7 179.7(3)
C4 C5 C6 C1 0.3(5)
C4 C5 C6 C7 178.4(3)
C8 N1 C7 O2 -3.0(4)
C8 N1 C7 C6 177.9(3)
C1 C6 C7 O2 5.3(4)
C5 C6 C7 O2 -172.7(3)
C1 C6 C7 N1 -175.6(3)
C5 C6 C7 N1 6.4(4)
C7 N1 C8 C9 83.6(4)
N1 C8 C9 N2 -84.9(3)
O3 C10 C11 C12 176.9(3)
C15 C10 C11 C12 -1.8(4)
O3 C10 C11 N3 -6.1(4)
C15 C10 C11 N3 175.2(2)
O5 N3 C11 C12 7.4(4)
O4 N3 C11 C12 -172.1(3)
O5 N3 C11 C10 -169.8(3)
O4 N3 C11 C10 10.7(4)
C10 C11 C12 C13 0.5(4)
N3 C11 C12 C13 -176.5(3)
C11 C12 C13 C14 0.6(4)
C11 C12 C13 N4 179.2(3)
O6 N4 C13 C12 4.6(5)
O7 N4 C13 C12 -174.3(3)
O6 N4 C13 C14 -176.8(3)
O7 N4 C13 C14 4.2(5)
C12 C13 C14 C15 -0.3(4)
N4 C13 C14 C15 -178.9(3)
C13 C14 C15 C10 -1.2(5)
C13 C14 C15 N5 178.6(3)
O3 C10 C15 C14 -176.6(3)
C11 C10 C15 C14 2.1(4)
O3 C10 C15 N5 3.6(4)
C11 C10 C15 N5 -177.6(2)
O9 N5 C15 C14 -141.6(3)
O8 N5 C15 C14 38.9(4)
O9 N5 C15 C10 38.1(4)
O8 N5 C15 C10 -141.3(3)
