#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/51/2235156.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_2235156
loop_
_publ_author_name
'Riahi, Sana'
'Mrad, Mohamed Lahbib'
'Ferretti, Valeria'
'Lefebvre, Frederic'
'Ben Nasr, Cherif'
_publ_section_title
;
 4-Acetamidoanilinium nitrate monohydrate
;
_journal_coeditor_code           LR2060
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1647
_journal_paper_doi               10.1107/S1600536812019393
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H11 N2 O1 +, N O3 -, H2 O'
_chemical_formula_moiety         'C8 H11 N2 O1 +, N O3 -, H2 O'
_chemical_formula_sum            'C8 H13 N3 O5'
_chemical_formula_weight         231.21
_chemical_name_systematic
;
4-Acetamidoanilinium nitrate monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.9420(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.10590(10)
_cell_length_b                   23.1112(5)
_cell_length_c                   11.4702(3)
_cell_measurement_reflns_used    4741
_cell_measurement_temperature    295
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      3.0
_cell_volume                     1087.00(5)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans'
_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  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4741
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.66
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0457
_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)+(0.0773P)²+0.1041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1422
_reflns_number_gt                1885
_reflns_number_total             2606
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            lr2060.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235156
_cod_database_fobs_code          2235156
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_occupancy
_atom_site_symmetry_multiplicity
O O1 0.1624(3) 0.11922(5) 0.45863(11) 0.0662(4) Uani d 1 1
O O2 0.6017(4) 0.36949(6) 0.53827(14) 0.0878(5) Uani d 1 1
O O3 0.3474(5) 0.30471(6) 0.63123(12) 0.0866(5) Uani d 1 1
O O4 0.3293(4) 0.30565(6) 0.44397(12) 0.0766(4) Uani d 1 1
O O1W 0.2790(3) 0.18436(6) 0.65055(11) 0.0570(3) Uani d 1 1
N N1 -0.0860(3) 0.09798(5) 0.28298(12) 0.0500(3) Uani d 1 1
N N2 0.2062(4) -0.13752(6) 0.21089(16) 0.0543(4) Uani d 1 1
N N3 0.4244(3) 0.32626(5) 0.53870(12) 0.0515(3) Uani d 1 1
C C1 0.0001(3) 0.03922(6) 0.27013(12) 0.0431(3) Uani d 1 1
C C2 0.1814(4) 0.00752(7) 0.35317(14) 0.0515(4) Uani d 1 1
C C3 0.2493(4) -0.05022(7) 0.33325(15) 0.0518(4) Uani d 1 1
C C4 0.1367(3) -0.07607(6) 0.23129(13) 0.0447(3) Uani d 1 1
C C5 -0.0431(4) -0.04540(7) 0.14791(15) 0.0524(4) Uani d 1 1
C C6 -0.1123(4) 0.01213(7) 0.16734(14) 0.0519(4) Uani d 1 1
C C7 -0.0072(4) 0.13406(6) 0.37245(13) 0.0480(4) Uani d 1 1
C C8 -0.1396(5) 0.19416(8) 0.3608(2) 0.0621(5) Uani d 1 1
H H1 0.259(4) 0.0238(8) 0.4267(17) 0.061(5) Uiso d 1 1
H H2 0.369(5) -0.0731(9) 0.3872(18) 0.065(5) Uiso d 1 1
H H3 -0.205(5) 0.1131(9) 0.2208(18) 0.060(5) Uiso d 1 1
H H4 0.374(5) -0.1507(9) 0.2619(18) 0.067(5) Uiso d 1 1
H H5 0.243(6) -0.1417(13) 0.135(3) 0.103(9) Uiso d 1 1
H H6 0.040(6) -0.1603(12) 0.239(2) 0.095(8) Uiso d 1 1
H H7 -0.229(4) 0.0345(9) 0.1086(19) 0.065(5) Uiso d 1 1
H H8 -0.123(5) -0.0614(9) 0.0796(18) 0.064(5) Uiso d 1 1
H H9 -0.251(9) 0.2023(17) 0.290(4) 0.141(12) Uiso d 1 1
H H10 0.017(8) 0.2231(14) 0.371(3) 0.115(9) Uiso d 1 1
H H11 -0.272(8) 0.2008(15) 0.415(3) 0.124(11) Uiso d 1 1
H H1W 0.219(6) 0.1691(11) 0.578(2) 0.087(7) Uiso d 1 1
H H2W 0.288(6) 0.2175(13) 0.639(2) 0.088(8) Uiso d 1 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
H1W O1W H2W 103(2)
C7 N1 C1 128.48(14)
C7 N1 H3 117.0(12)
C1 N1 H3 114.4(12)
C4 N2 H4 111.1(13)
C4 N2 H5 107.7(19)
H4 N2 H5 115(2)
C4 N2 H6 109.9(16)
H4 N2 H6 97.5(19)
H5 N2 H6 116(2)
O3 N3 O4 121.44(15)
O3 N3 O2 120.58(15)
O4 N3 O2 117.98(14)
C2 C1 C6 119.12(14)
C2 C1 N1 124.34(14)
C6 C1 N1 116.53(13)
C3 C2 C1 120.07(15)
C3 C2 H1 117.5(11)
C1 C2 H1 122.4(11)
C4 C3 C2 119.89(15)
C4 C3 H2 117.5(13)
C2 C3 H2 122.6(13)
C3 C4 C5 120.93(14)
C3 C4 N2 119.78(14)
C5 C4 N2 119.29(14)
C4 C5 C6 119.47(15)
C4 C5 H8 123.0(13)
C6 C5 H8 117.5(13)
C5 C6 C1 120.52(15)
C5 C6 H7 120.4(12)
C1 C6 H7 119.0(12)
O1 C7 N1 122.92(14)
O1 C7 C8 121.34(15)
N1 C7 C8 115.75(15)
C7 C8 H9 115(2)
C7 C8 H10 114.1(18)
H9 C8 H10 106(3)
C7 C8 H11 110(2)
H9 C8 H11 107(3)
H10 C8 H11 104(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2286(19)
O2 N3 1.2363(18)
O3 N3 1.2284(19)
O4 N3 1.2314(18)
O1W H1W 0.93(3)
O1W H2W 0.78(3)
N1 C7 1.349(2)
N1 C1 1.4129(19)
N1 H3 0.91(2)
N2 C4 1.4698(19)
N2 H4 0.93(2)
N2 H5 0.89(3)
N2 H6 0.93(3)
C1 C2 1.387(2)
C1 C6 1.393(2)
C2 C3 1.385(2)
C2 H1 0.96(2)
C3 C4 1.372(2)
C3 H2 0.93(2)
C4 C5 1.375(2)
C5 C6 1.380(2)
C5 H8 0.91(2)
C6 H7 0.96(2)
C7 C8 1.495(2)
C8 H9 0.93(4)
C8 H10 0.93(3)
C8 H11 0.86(4)
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
O1W H1W O1 . 0.93(3) 1.79(3) 2.689(2) 161(3)
O1W H2W O3 . 0.78(3) 2.03(3) 2.805(2) 172(3)
N1 H3 O2 4_465 0.91(2) 2.24(2) 3.117(2) 161(2)
N2 H4 O1W 3_656 0.93(2) 1.87(2) 2.796(2) 173(2)
N2 H5 O2 2_645 0.89(3) 2.14(3) 3.008(2) 165(3)
N2 H6 O1W 3_556 0.93(3) 1.95(2) 2.827(2) 156(2)
