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#$Date: 2018-01-30 09:15:10 +0200 (Tue, 30 Jan 2018) $
#$Revision: 205880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/23/2242359.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_2242359
loop_
_publ_author_name
'Mishra, Risha'
'Rangan, Krishnan'
'Pallepogu, Raghavaiah'
_publ_section_title
;
 Crystal structure of a new molecular salt: 4-aminobenzenaminium
 5-carboxypentanoate
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              201
_journal_page_last               205
_journal_paper_doi               10.1107/S2056989018000737
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C6 H9 N2 +, C6 H9 O4 -'
_chemical_formula_moiety         'C6 H9 N2 +, C6 H9 O4 -'
_chemical_formula_sum            'C12 H18 N2 O4'
_chemical_formula_weight         254.28
_chemical_name_common
;
4-Aminobenzenaminium 5-carboxypentanoate
;
_chemical_name_systematic
;
4-Aminoanilinium 5-carboxypentanoate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                92.069(6)
_cell_angle_beta                 104.165(6)
_cell_angle_gamma                97.172(5)
_cell_formula_units_Z            1
_cell_length_a                   5.2918(3)
_cell_length_b                   7.1666(4)
_cell_length_c                   8.4205(7)
_cell_measurement_reflns_used    5347
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.2130
_cell_measurement_theta_min      5.1990
_cell_volume                     306.47(4)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et
al.,  2008)
;
_computing_publication_material
;
SHELXL2016/6 (Sheldrick, 2015), OLEX2
(Dolomanov et al., 2009),
PLATON (Spek, 2009) and publCIF (Westrip (2010)
;
_computing_structure_refinement
;
SHELXL2016/6 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku Oxford Diffraction XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3776
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.130
_diffrn_reflns_theta_min         5.006
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             136
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.320
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.218
_refine_ls_extinction_coef       0.15(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
(SHELXL-2016/6; Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0483P)²+0.0998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                1341
_reflns_number_total             1416
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dx2003sup1.cif
_cod_data_source_block           I
_cod_database_code               2242359
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.968
loop_
_space_group_symop_operation_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_occupancy
O O1 0.88613(16) 0.51078(11) 0.73311(10) 0.0284(2) Uani d 1
O O2 0.62365(13) 0.36690(9) 0.50333(8) 0.0159(2) Uani d 1
H H2O 0.500000 0.500000 0.500000 0.079(10) Uiso d 1
C C4 0.90322(17) 0.07097(12) 0.49487(11) 0.0140(2) Uani d 1
H H4A 0.867169 0.119848 0.384244 0.017 Uiso calc 1
H H4B 0.735161 0.007357 0.511087 0.017 Uiso calc 1
C C5 1.01023(17) 0.23441(12) 0.62353(11) 0.0127(2) Uani d 1
H H5A 1.048177 0.183438 0.733310 0.015 Uiso calc 1
H H5B 1.178973 0.295883 0.606644 0.015 Uiso calc 1
C C6 0.82994(17) 0.38253(12) 0.62270(11) 0.0122(2) Uani d 1
N N1 0.43897(17) 0.62290(12) 0.87167(10) 0.0177(2) Uani d 1
H H1NA 0.268(3) 0.582(2) 0.8186(19) 0.033(4) Uiso d 1
H H1NB 0.538(3) 0.608(2) 0.800(2) 0.036(4) Uiso d 1
H H1NC 0.470(5) 0.534(3) 0.953(3) 0.013(6) Uiso d 0.5
C C1 0.47080(18) 0.81542(13) 0.93517(11) 0.0147(2) Uani d 1
C C2 0.65701(19) 0.95024(15) 0.89941(12) 0.0180(2) Uani d 1
H H2 0.764255 0.916272 0.830590 0.022 Uiso calc 1
C C3 0.68658(19) 1.13477(14) 0.96421(12) 0.0179(2) Uani d 1
H H3 0.814280 1.227114 0.939883 0.021 Uiso calc 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
C6 O2 H2O . . 113.50(6)
C5 C4 C4 . 2_756 111.39(9)
C5 C4 H4A . . 109.3
C4 C4 H4A 2_756 . 109.3
C5 C4 H4B . . 109.3
C4 C4 H4B 2_756 . 109.3
H4A C4 H4B . . 108.0
C6 C5 C4 . . 115.04(8)
C6 C5 H5A . . 108.5
C4 C5 H5A . . 108.5
C6 C5 H5B . . 108.5
C4 C5 H5B . . 108.5
H5A C5 H5B . . 107.5
O1 C6 O2 . . 123.47(8)
O1 C6 C5 . . 120.06(8)
O2 C6 C5 . . 116.47(8)
C1 N1 H1NA . . 111.1(9)
C1 N1 H1NB . . 111.9(10)
H1NA N1 H1NB . . 107.8(14)
C1 N1 H1NC . . 114.7(15)
H1NA N1 H1NC . . 101.0(18)
H1NB N1 H1NC . . 109.6(18)
C2 C1 C3 . 2_677 120.02(9)
C2 C1 N1 . . 121.06(8)
C3 C1 N1 2_677 . 118.91(9)
C1 C2 C3 . . 119.97(9)
C1 C2 H2 . . 120.0
C3 C2 H2 . . 120.0
C2 C3 C1 . 2_677 120.01(9)
C2 C3 H3 . . 120.0
C1 C3 H3 2_677 . 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C6 . 1.2379(12)
O2 C6 . 1.2802(11)
O2 H2O . 1.2197(6)
C4 C5 . 1.5195(12)
C4 C4 2_756 1.5213(16)
C4 H4A . 0.9900
C4 H4B . 0.9900
C5 C6 . 1.5123(12)
C5 H5A . 0.9900
C5 H5B . 0.9900
N1 C1 . 1.4361(13)
N1 H1NA . 0.914(17)
N1 H1NB . 0.906(17)
N1 H1NC . 0.95(2)
C1 C2 . 1.3870(14)
C1 C3 2_677 1.3916(13)
C2 C3 . 1.3876(14)
C2 H2 . 0.9500
C3 H3 . 0.9500
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
O2 H2O O2 2_666 1.22 1.22 2.4390(10) 180 yes
O2 H2O O1 2_666 1.22 2.45 3.1780(10) 116 yes
N1 H1NA O1 1_455 0.91(2) 1.97(2) 2.8710(10) 171.0(10) yes
N1 H1NB O1 . 0.90(2) 2.24(2) 3.0600(10) 152.0(10) yes
N1 H1NB O2 2_666 0.90(2) 2.51(2) 3.0980(10) 123.0(10) yes
N1 H1NC N1 2_667 0.95(2) 1.89(2) 2.8400(10) 174(2) yes
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_4
_geom_torsion
C4 C4 C5 C6 2_756 . -179.82(9)
C4 C5 C6 O1 . . 172.41(9)
C4 C5 C6 O2 . . -8.04(12)
C3 C1 C2 C3 2_677 . 0.09(16)
N1 C1 C2 C3 . . -179.06(9)
C1 C2 C3 C1 . 2_677 -0.10(16)
