#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/02/2210274.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_2210274
loop_
_publ_author_name
'Zhao, Li-Fang'
_publ_section_title
;
 2-[2-(Methylammonio)ethyliminiomethyl]-4-nitrophenolate nitrate
;
_journal_coeditor_code           HG2094
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3970
_journal_page_last               o3971
_journal_paper_doi               10.1107/S1600536806032594
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C10 H14 N3 O3 +, N O3 -'
_chemical_formula_moiety         'C10 H14 N3 O3 +, N O3 -'
_chemical_formula_sum            'C10 H14 N4 O6'
_chemical_formula_weight         286.25
_chemical_name_systematic
;
2-[2-(Methylammonio)ethyliminiomethyl]-4-nitrophenolate nitrate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.119(2)
_cell_length_b                   16.922(4)
_cell_length_c                   20.671(5)
_cell_measurement_reflns_used    693
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.3
_cell_measurement_theta_min      2.4
_cell_volume                     2490.2(11)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1034
_diffrn_reflns_av_sigmaI/netI    0.0944
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13625
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_correction_T_min  0.9799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2564
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1365
_refine_ls_R_factor_gt           0.0707
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0371P)²+2.2208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1643
_reflns_number_gt                1430
_reflns_number_total             2564
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2094.cif
_cod_data_source_block           I
_cod_database_code               2210274
_cod_database_fobs_code          2210274
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
O O1 0.6212(6) 0.47863(19) 0.27171(18) 0.0992(14) Uani d . 1
O O2 0.6643(4) 0.48186(15) 0.37410(15) 0.0600(9) Uani d . 1
O O3 1.0208(3) 0.15519(13) 0.31232(11) 0.0394(7) Uani d . 1
O O4 0.6855(5) 0.09757(17) 0.51453(13) 0.0673(9) Uani d . 1
O O5 0.8001(5) 0.21127(15) 0.54009(14) 0.0692(10) Uani d . 1
O O6 0.8237(4) 0.11342(15) 0.60515(14) 0.0571(8) Uani d . 1
N N1 0.6790(5) 0.44867(19) 0.32137(19) 0.0505(9) Uani d . 1
N N2 0.9874(4) 0.16040(16) 0.18660(14) 0.0316(7) Uani d D 1
N N3 0.7217(4) 0.05317(15) 0.10461(13) 0.0319(7) Uani d . 1
H H3A 0.6716 0.0045 0.1080 0.038 Uiso calc R 1
H H3B 0.6730 0.0828 0.1366 0.038 Uiso calc R 1
N N4 0.7695(4) 0.14151(18) 0.55242(15) 0.0417(8) Uani d . 1
C C1 0.8835(5) 0.26283(17) 0.25723(16) 0.0276(8) Uani d . 1
C C2 0.9404(5) 0.22234(19) 0.31476(17) 0.0317(8) Uani d . 1
C C3 0.9009(5) 0.2614(2) 0.37426(17) 0.0411(9) Uani d . 1
H H3 0.9324 0.2367 0.4130 0.049 Uiso calc R 1
C C4 0.8182(5) 0.3338(2) 0.37600(19) 0.0439(10) Uani d . 1
H H4 0.7953 0.3581 0.4156 0.053 Uiso calc R 1
C C5 0.7675(5) 0.3720(2) 0.31888(19) 0.0383(9) Uani d . 1
C C6 0.7998(5) 0.33723(19) 0.25997(17) 0.0349(9) Uani d . 1
H H6 0.7660 0.3632 0.2221 0.042 Uiso calc R 1
C C7 0.9143(5) 0.22933(18) 0.19488(17) 0.0303(8) Uani d . 1
H H7 0.8802 0.2585 0.1586 0.036 Uiso calc R 1
C C8 1.0275(5) 0.12536(19) 0.12326(17) 0.0357(9) Uani d . 1
H H8A 1.1619 0.1175 0.1189 0.043 Uiso calc R 1
H H8B 0.9877 0.1615 0.0895 0.043 Uiso calc R 1
C C9 0.9280(5) 0.04709(19) 0.11460(18) 0.0349(9) Uani d . 1
H H9A 0.9826 0.0201 0.0777 0.042 Uiso calc R 1
H H9B 0.9511 0.0148 0.1525 0.042 Uiso calc R 1
C C10 0.6638(6) 0.0874(2) 0.04214(18) 0.0494(11) Uani d . 1
H H10A 0.7101 0.1405 0.0389 0.074 Uiso calc R 1
H H10B 0.5291 0.0877 0.0394 0.074 Uiso calc R 1
H H10C 0.7143 0.0562 0.0075 0.074 Uiso calc R 1
H H2 1.020(6) 0.134(2) 0.2232(13) 0.083(17) Uiso d 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'
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
O1 N1 O2 121.9(4)
O1 N1 C5 119.5(3)
O2 N1 C5 118.6(4)
C7 N2 C8 124.3(3)
C7 N2 H2 116(3)
C8 N2 H2 120(3)
C10 N3 C9 115.2(3)
C10 N3 H3A 108.5
C9 N3 H3A 108.5
C10 N3 H3B 108.5
C9 N3 H3B 108.5
H3A N3 H3B 107.5
O5 N4 O4 122.2(3)
O5 N4 O6 119.5(3)
O4 N4 O6 118.3(3)
C6 C1 C7 117.5(3)
C6 C1 C2 121.3(3)
C7 C1 C2 121.2(3)
O3 C2 C3 122.5(3)
O3 C2 C1 121.4(3)
C3 C2 C1 116.1(3)
C4 C3 C2 121.8(3)
C4 C3 H3 119.1
C2 C3 H3 119.1
C3 C4 C5 120.5(3)
C3 C4 H4 119.8
C5 C4 H4 119.8
C6 C5 C4 120.7(3)
C6 C5 N1 119.4(4)
C4 C5 N1 119.9(3)
C5 C6 C1 119.6(3)
C5 C6 H6 120.2
C1 C6 H6 120.2
N2 C7 C1 122.9(3)
N2 C7 H7 118.6
C1 C7 H7 118.6
N2 C8 C9 111.7(3)
N2 C8 H8A 109.3
C9 C8 H8A 109.3
N2 C8 H8B 109.3
C9 C8 H8B 109.3
H8A C8 H8B 108.0
N3 C9 C8 114.7(3)
N3 C9 H9A 108.6
C8 C9 H9A 108.6
N3 C9 H9B 108.6
C8 C9 H9B 108.6
H9A C9 H9B 107.6
N3 C10 H10A 109.5
N3 C10 H10B 109.5
H10A C10 H10B 109.5
N3 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.217(4)
O2 N1 1.231(4)
O3 C2 1.273(4)
O4 N4 1.235(4)
O5 N4 1.227(4)
O6 N4 1.250(4)
N1 C5 1.444(5)
N2 C7 1.289(4)
N2 C8 1.465(4)
N2 H2 0.91(3)
N3 C10 1.474(4)
N3 C9 1.487(4)
N3 H3A 0.9000
N3 H3B 0.9000
C1 C6 1.394(4)
C1 C7 1.425(5)
C1 C2 1.431(5)
C2 C3 1.424(5)
C3 C4 1.360(5)
C3 H3 0.9300
C4 C5 1.393(5)
C4 H4 0.9300
C5 C6 1.372(5)
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.513(4)
C8 H8A 0.9700
C8 H8B 0.9700
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
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
N3 H3A O6 2_654 0.90 2.00 2.838(5) 154.9
N3 H3A O2 3_645 0.90 2.45 3.033(4) 122.8
N3 H3B O3 6_556 0.90 1.95 2.824(4) 164.6
N2 H2 O3 . 0.91(3) 1.88(3) 2.611(4) 137(4)
