#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/94/2229460.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_2229460
loop_
_publ_author_name
'Pourayoubi, Mehrdad'
'Eshtiagh-Hosseini, Hossein'
'Sanaei Ataabadi, Somayyeh'
'Mancilla Percino, Teresa'
'A. Leyva Ramírez, Marco'
_publ_section_title
;
 9-Aminoacridinium nitrate monohydrate
;
_journal_coeditor_code           NG5102
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o565
_journal_paper_doi               10.1107/S1600536811003953
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H11 N2 +, N O3 -, H2 O'
_chemical_formula_moiety         'C13 H11 N2 +, N O3 -, H2 O'
_chemical_formula_sum            'C13 H13 N3 O4'
_chemical_formula_weight         275.26
_chemical_name_systematic
;
9-Aminoacridinium nitrate monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                117.0160(10)
_cell_angle_beta                 94.1380(10)
_cell_angle_gamma                97.9950(10)
_cell_formula_units_Z            2
_cell_length_a                   6.8556(2)
_cell_length_b                   10.0532(2)
_cell_length_c                   10.5912(3)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      1
_cell_volume                     636.36(3)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material
'WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8945
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9526
_exptl_absorpt_correction_T_min  0.9228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.75
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2822
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0450
_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)+(0.0799P)²+0.0299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1324
_reflns_number_gt                2054
_reflns_number_total             2822
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng5102.cif
_cod_data_source_block           I
_cod_database_code               2229460
_cod_database_fobs_code          2229460
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.28645(17) 0.69390(14) 0.48088(14) 0.0392(3) Uani d . 1 . .
C C2 0.3072(2) 0.82982(15) 0.46976(16) 0.0491(3) Uani d . 1 . .
H H2 0.3418 0.9237 0.5518 0.059 Uiso calc R 1 . .
C C3 0.2764(2) 0.82263(16) 0.33871(17) 0.0548(4) Uani d . 1 . .
H H3 0.2900 0.9123 0.3317 0.066 Uiso calc R 1 . .
C C4 0.2245(2) 0.68227(17) 0.21357(17) 0.0545(4) Uani d . 1 . .
H H4 0.2054 0.6794 0.1245 0.065 Uiso calc R 1 . .
C C5 0.20191(19) 0.54989(15) 0.22257(14) 0.0456(3) Uani d . 1 . .
H H5 0.1663 0.4572 0.1393 0.055 Uiso calc R 1 . .
C C6 0.23215(17) 0.55232(13) 0.35736(13) 0.0377(3) Uani d . 1 . .
C C7 0.20689(17) 0.41608(13) 0.37264(13) 0.0368(3) Uani d . 1 . .
C C8 0.23830(16) 0.43023(13) 0.51410(13) 0.0369(3) Uani d . 1 . .
C C9 0.21635(19) 0.30332(15) 0.54077(15) 0.0438(3) Uani d . 1 . .
H H9 0.1779 0.2057 0.4642 0.053 Uiso calc R 1 . .
C C10 0.2506(2) 0.32195(17) 0.67683(16) 0.0513(4) Uani d . 1 . .
H H10 0.2353 0.2375 0.6924 0.062 Uiso calc R 1 . .
C C11 0.3088(2) 0.46790(18) 0.79260(16) 0.0554(4) Uani d . 1 . .
H H11 0.3326 0.4797 0.8850 0.066 Uiso calc R 1 . .
C C12 0.3312(2) 0.59339(17) 0.77252(14) 0.0512(4) Uani d . 1 . .
H H12 0.3695 0.6900 0.8507 0.061 Uiso calc R 1 . .
C C13 0.29601(17) 0.57631(14) 0.63302(13) 0.0393(3) Uani d . 1 . .
N N1 0.31813(16) 0.70224(12) 0.61313(12) 0.0437(3) Uani d D 1 . .
N N2 0.15562(19) 0.28113(13) 0.25875(12) 0.0507(3) Uani d D 1 . .
N N3 0.0612(2) 1.10579(12) 0.88933(12) 0.0521(3) Uani d . 1 . .
O O1 0.22383(17) 1.19337(12) 0.95048(12) 0.0721(4) Uani d . 1 . .
O O2 0.04483(18) 1.00530(11) 0.76309(11) 0.0674(3) Uani d . 1 . .
O O3 -0.08334(18) 1.12104(15) 0.95548(12) 0.0739(4) Uani d . 1 . .
O O4 0.4979(2) 0.98619(13) 0.83821(14) 0.0775(4) Uani d D 1 . .
H H1 0.361(2) 0.7928(17) 0.6889(16) 0.062(5) Uiso d D 1 . .
H H2A 0.133(2) 0.2695(19) 0.1668(16) 0.061(4) Uiso d D 1 . .
H H2B 0.126(2) 0.1971(17) 0.2686(18) 0.067(5) Uiso d D 1 . .
H H4A 0.626(2) 1.017(2) 0.883(2) 0.094(7) Uiso d D 1 . .
H H4B 0.422(3) 1.057(2) 0.875(2) 0.098(7) 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C6 . . 120.53(11) ?
N1 C1 C2 . . 119.19(12) ?
C6 C1 C2 . . 120.28(12) ?
C3 C2 C1 . . 119.60(13) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
C2 C3 C4 . . 121.12(13) ?
C2 C3 H3 . . 119.4 ?
C4 C3 H3 . . 119.4 ?
C5 C4 C3 . . 120.01(13) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.69(13) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C1 C6 C5 . . 118.30(11) ?
C1 C6 C7 . . 118.91(11) ?
C5 C6 C7 . . 122.78(11) ?
N2 C7 C8 . . 120.83(11) ?
N2 C7 C6 . . 120.48(11) ?
C8 C7 C6 . . 118.70(11) ?
C13 C8 C9 . . 117.72(11) ?
C13 C8 C7 . . 119.16(11) ?
C9 C8 C7 . . 123.11(11) ?
C10 C9 C8 . . 121.15(13) ?
C10 C9 H9 . . 119.4 ?
C8 C9 H9 . . 119.4 ?
C9 C10 C11 . . 119.94(13) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C12 C11 C10 . . 121.11(13) ?
C12 C11 H11 . . 119.4 ?
C10 C11 H11 . . 119.4 ?
C11 C12 C13 . . 119.71(13) ?
C11 C12 H12 . . 120.1 ?
C13 C12 H12 . . 120.1 ?
N1 C13 C12 . . 119.63(12) ?
N1 C13 C8 . . 120.00(11) ?
C12 C13 C8 . . 120.37(12) ?
C1 N1 C13 . . 122.68(11) ?
C1 N1 H1 . . 118.7(11) ?
C13 N1 H1 . . 118.6(11) ?
C7 N2 H2A . . 122.2(10) ?
C7 N2 H2B . . 120.4(11) ?
H2A N2 H2B . . 116.9(16) ?
O2 N3 O1 . . 119.79(14) ?
O2 N3 O3 . . 120.94(13) ?
O1 N3 O3 . . 119.27(12) ?
H4A O4 H4B . . 114(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
C1 N1 . 1.3641(18) ?
C1 C6 . 1.4024(18) ?
C1 C2 . 1.4127(18) ?
C2 C3 . 1.356(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.403(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.3654(19) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.4163(18) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.4393(17) ?
C7 N2 . 1.3186(16) ?
C7 C8 . 1.4361(17) ?
C8 C13 . 1.4091(18) ?
C8 C9 . 1.4178(17) ?
C9 C10 . 1.364(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.396(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.362(2) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.4061(19) ?
C12 H12 . 0.9300 ?
C13 N1 . 1.3650(17) ?
N1 H1 . 0.887(14) ?
N2 H2A . 0.925(14) ?
N2 H2B . 0.895(14) ?
N3 O2 . 1.2411(15) ?
N3 O1 . 1.2417(16) ?
N3 O3 . 1.2417(17) ?
O4 H4A . 0.909(16) ?
O4 H4B . 0.901(16) ?
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
N2 H2A O1 1_544 0.925(14) 2.230(15) 3.0619(17) 149.4(14)
N2 H2A O3 1_544 0.925(14) 2.304(15) 3.0662(16) 139.5(13)
N2 H2B O2 2_566 0.895(14) 2.070(14) 2.9123(15) 156.5(15)
O4 H4A O3 1_655 0.909(16) 2.030(17) 2.9147(18) 164.1(19)
N1 H1 O4 . 0.887(14) 1.909(14) 2.7867(15) 169.6(15)
O4 H4B O1 . 0.901(16) 2.010(16) 2.9058(18) 173(2)
O4 H4B O2 . 0.901(16) 2.64(2) 3.2039(19) 121.5(18)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . 179.86(12) ?
C6 C1 C2 C3 . . . . -0.71(19) ?
C1 C2 C3 C4 . . . . -0.1(2) ?
C2 C3 C4 C5 . . . . 0.7(2) ?
C3 C4 C5 C6 . . . . -0.6(2) ?
N1 C1 C6 C5 . . . . -179.71(11) ?
C2 C1 C6 C5 . . . . 0.87(17) ?
N1 C1 C6 C7 . . . . 1.12(17) ?
C2 C1 C6 C7 . . . . -178.31(10) ?
C4 C5 C6 C1 . . . . -0.23(19) ?
C4 C5 C6 C7 . . . . 178.91(11) ?
C1 C6 C7 N2 . . . . 179.90(11) ?
C5 C6 C7 N2 . . . . 0.77(19) ?
C1 C6 C7 C8 . . . . -0.01(16) ?
C5 C6 C7 C8 . . . . -179.14(11) ?
N2 C7 C8 C13 . . . . 179.02(11) ?
C6 C7 C8 C13 . . . . -1.08(16) ?
N2 C7 C8 C9 . . . . -0.21(19) ?
C6 C7 C8 C9 . . . . 179.70(10) ?
C13 C8 C9 C10 . . . . -0.24(18) ?
C7 C8 C9 C10 . . . . 179.00(11) ?
C8 C9 C10 C11 . . . . -0.1(2) ?
C9 C10 C11 C12 . . . . 0.4(2) ?
C10 C11 C12 C13 . . . . -0.2(2) ?
C11 C12 C13 N1 . . . . 179.87(12) ?
C11 C12 C13 C8 . . . . -0.1(2) ?
C9 C8 C13 N1 . . . . -179.64(10) ?
C7 C8 C13 N1 . . . . 1.09(17) ?
C9 C8 C13 C12 . . . . 0.38(17) ?
C7 C8 C13 C12 . . . . -178.89(11) ?
C6 C1 N1 C13 . . . . -1.16(18) ?
C2 C1 N1 C13 . . . . 178.27(10) ?
C12 C13 N1 C1 . . . . -179.99(11) ?
C8 C13 N1 C1 . . . . 0.03(18) ?
