#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/79/2017909.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2017909
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
_publ_section_title
;
 Hydrogen bonding in the anhydrous 1:1 proton-transfer compounds of
 isonipecotamide with nitro-substituted benzoic acids: the salts of the
 three isomeric mononitrobenzoic acids and of 3,5-dinitrobenzoic acid
;
_journal_coeditor_code           SU3056
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o614
_journal_page_last               o618
_journal_paper_doi               10.1107/S0108270110045750
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H13 N2 O + , C7 H3 N2 O6 -'
_chemical_formula_moiety         'C6 H13 N2 O +, C7 H3 N2 O6 -'
_chemical_formula_sum            'C13 H16 N4 O7'
_chemical_formula_weight         340.30
_chemical_melting_point_gt       473
_chemical_melting_point_lt       475
_chemical_name_common            'isonipecotamide 3,5-dinitrobenzoate'
_chemical_name_systematic
;
4-carbamoylpiperidinium 3,5-dinitrobenzoate
;
_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           SHELXL97
_cell_angle_alpha                111.370(8)
_cell_angle_beta                 99.504(7)
_cell_angle_gamma                100.772(8)
_cell_formula_units_Z            2
_cell_length_a                   5.7159(5)
_cell_length_b                   11.9970(12)
_cell_length_c                   12.6447(10)
_cell_measurement_reflns_used    3824
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.7
_cell_measurement_theta_min      3.08
_cell_volume                     767.04(14)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)
;
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Gemini-S Ultra CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9445
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.09
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0397
_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)+(0.0464P)²+0.0623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0924
_reflns_number_gt                2279
_reflns_number_total             2996
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su3056.cif
_cod_data_source_block           IV
_cod_database_code               2017909
_cod_database_fobs_code          2017909
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O41A 0.0238(2) 0.94674(11) 0.12385(10) 0.0368(4) Uani . . 1.000
N N1A 0.4414(3) 0.69533(13) 0.25966(12) 0.0313(5) Uani . . 1.000
N N41A 0.2169(3) 0.91229(13) -0.02221(12) 0.0304(4) Uani . . 1.000
C C2A 0.4128(3) 0.64556(16) 0.13017(14) 0.0359(6) Uani . . 1.000
C C3A 0.2496(3) 0.70614(15) 0.07572(14) 0.0304(5) Uani . . 1.000
C C4A 0.3521(3) 0.84774(14) 0.13217(13) 0.0273(5) Uani . . 1.000
C C5A 0.3880(3) 0.89615(15) 0.26500(13) 0.0334(5) Uani . . 1.000
C C6A 0.5495(3) 0.83224(16) 0.31662(14) 0.0356(6) Uani . . 1.000
C C41A 0.1842(3) 0.90734(14) 0.07838(13) 0.0269(5) Uani . . 1.000
O O11 0.9403(2) 0.58841(12) 0.23351(11) 0.0435(4) Uani . . 1.000
O O12 0.6878(2) 0.56279(11) 0.34513(10) 0.0371(4) Uani . . 1.000
O O31 0.7183(2) 0.25715(13) 0.50782(12) 0.0527(5) Uani . . 1.000
O O32 0.9621(3) 0.13842(13) 0.47058(13) 0.0593(6) Uani . . 1.000
O O51 1.4706(2) 0.16989(12) 0.20496(12) 0.0534(5) Uani . . 1.000
O O52 1.4018(2) 0.28118(15) 0.10752(12) 0.0605(5) Uani . . 1.000
N N3 0.8779(3) 0.22183(14) 0.46136(12) 0.0393(5) Uani . . 1.000
N N5 1.3703(2) 0.24465(14) 0.18419(13) 0.0416(5) Uani . . 1.000
C C1 0.9562(3) 0.43419(14) 0.30805(12) 0.0259(4) Uani . . 1.000
C C2 0.8795(3) 0.37918(14) 0.38042(12) 0.0263(5) Uani . . 1.000
C C3 0.9707(3) 0.28290(15) 0.38908(13) 0.0284(5) Uani . . 1.000
C C4 1.1348(3) 0.23763(15) 0.32766(14) 0.0319(5) Uani . . 1.000
C C5 1.2050(3) 0.29341(15) 0.25593(13) 0.0307(5) Uani . . 1.000
C C6 1.1204(3) 0.39006(15) 0.24469(13) 0.0294(5) Uani . . 1.000
C C11 0.8538(3) 0.53762(15) 0.29406(14) 0.0296(5) Uani . . 1.000
H H4A 0.51320 0.86850 0.11650 0.0330 Uiso calc R 1.000
H H11A 0.283(3) 0.6745(16) 0.2719(14) 0.034(4) Uiso . . 1.000
H H12A 0.542(4) 0.652(2) 0.2898(18) 0.062(6) Uiso . . 1.000
H H21A 0.34100 0.55630 0.09560 0.0430 Uiso calc R 1.000
H H22A 0.57320 0.66170 0.11430 0.0430 Uiso calc R 1.000
H H31A 0.08530 0.68400 0.08590 0.0370 Uiso calc R 1.000
H H32A 0.23790 0.67560 -0.00790 0.0370 Uiso calc R 1.000
H H41A 0.332(4) 0.8823(18) -0.0494(17) 0.049(6) Uiso . . 1.000
H H42A 0.135(3) 0.9531(17) -0.0548(15) 0.038(5) Uiso . . 1.000
H H51A 0.46370 0.98510 0.30060 0.0400 Uiso calc R 1.000
H H52A 0.22910 0.88140 0.28250 0.0400 Uiso calc R 1.000
H H61A 0.71290 0.85250 0.30480 0.0430 Uiso calc R 1.000
H H62A 0.56460 0.86170 0.40040 0.0430 Uiso calc R 1.000
H H2 0.76780 0.40680 0.42270 0.0320 Uiso calc R 1.000
H H4 1.19480 0.17290 0.33430 0.0380 Uiso calc R 1.000
H H6 1.17280 0.42520 0.19520 0.0350 Uiso calc R 1.000
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2A N1A C6A . . . 111.66(14) no
H11A N1A H12A . . . 108.3(18) no
C2A N1A H12A . . . 107.0(12) no
C6A N1A H11A . . . 110.2(12) no
C2A N1A H11A . . . 107.3(10) no
C6A N1A H12A . . . 112.1(14) no
C41A N41A H42A . . . 120.4(11) no
H41A N41A H42A . . . 121.8(18) no
C41A N41A H41A . . . 117.4(14) no
O32 N3 C3 . . . 118.39(16) no
O31 N3 O32 . . . 124.01(17) no
O31 N3 C3 . . . 117.60(16) no
O51 N5 C5 . . . 118.14(15) no
O52 N5 C5 . . . 118.22(15) no
O51 N5 O52 . . . 123.64(14) no
N1A C2A C3A . . . 110.18(14) no
C2A C3A C4A . . . 110.96(14) no
C5A C4A C41A . . . 111.63(14) no
C3A C4A C41A . . . 110.39(14) no
C3A C4A C5A . . . 110.00(14) no
C4A C5A C6A . . . 110.83(14) no
N1A C6A C5A . . . 110.25(14) no
O41A C41A N41A . . . 122.33(16) no
O41A C41A C4A . . . 121.88(14) no
N41A C41A C4A . . . 115.78(15) no
N1A C2A H21A . . . 110.00 no
C3A C2A H22A . . . 110.00 no
N1A C2A H22A . . . 110.00 no
C3A C2A H21A . . . 110.00 no
H21A C2A H22A . . . 108.00 no
C4A C3A H31A . . . 109.00 no
C2A C3A H31A . . . 109.00 no
C2A C3A H32A . . . 109.00 no
H31A C3A H32A . . . 108.00 no
C4A C3A H32A . . . 109.00 no
C3A C4A H4A . . . 108.00 no
C41A C4A H4A . . . 108.00 no
C5A C4A H4A . . . 108.00 no
C6A C5A H51A . . . 109.00 no
C4A C5A H52A . . . 109.00 no
C4A C5A H51A . . . 109.00 no
C6A C5A H52A . . . 109.00 no
H51A C5A H52A . . . 108.00 no
H61A C6A H62A . . . 108.00 no
N1A C6A H61A . . . 110.00 no
N1A C6A H62A . . . 110.00 no
C5A C6A H61A . . . 110.00 no
C5A C6A H62A . . . 110.00 no
C2 C1 C6 . . . 119.13(16) no
C2 C1 C11 . . . 120.61(15) no
C6 C1 C11 . . . 120.21(15) no
C1 C2 C3 . . . 119.41(16) no
N3 C3 C2 . . . 118.55(15) no
N3 C3 C4 . . . 118.65(17) no
C2 C3 C4 . . . 122.70(16) no
C3 C4 C5 . . . 116.36(17) no
N5 C5 C4 . . . 118.51(16) no
N5 C5 C6 . . . 118.27(15) no
C4 C5 C6 . . . 123.17(16) no
C1 C6 C5 . . . 119.23(16) no
O11 C11 O12 . . . 126.51(18) no
O11 C11 C1 . . . 117.67(15) no
O12 C11 C1 . . . 115.82(16) no
C1 C2 H2 . . . 120.00 no
C3 C2 H2 . . . 120.00 no
C3 C4 H4 . . . 122.00 no
C5 C4 H4 . . . 122.00 no
C1 C6 H6 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O41A C41A . . 1.238(2) no
O11 C11 . . 1.247(2) no
O12 C11 . . 1.255(2) no
O31 N3 . . 1.224(2) no
O32 N3 . . 1.222(2) no
O51 N5 . . 1.231(2) no
O52 N5 . . 1.226(2) no
N1A C6A . . 1.487(3) no
N1A C2A . . 1.492(2) no
N41A C41A . . 1.336(2) no
N1A H12A . . 0.96(2) no
N1A H11A . . 0.947(18) no
N41A H42A . . 0.89(2) no
N41A H41A . . 0.87(2) no
N3 C3 . . 1.468(2) no
N5 C5 . . 1.470(2) no
C2A C3A . . 1.509(3) no
C3A C4A . . 1.531(3) no
C4A C41A . . 1.513(2) no
C4A C5A . . 1.527(2) no
C5A C6A . . 1.515(3) no
C2A H21A . . 0.9700 no
C2A H22A . . 0.9700 no
C3A H32A . . 0.9700 no
C3A H31A . . 0.9700 no
C4A H4A . . 0.9800 no
C5A H51A . . 0.9700 no
C5A H52A . . 0.9700 no
C6A H61A . . 0.9700 no
C6A H62A . . 0.9700 no
C1 C2 . . 1.389(2) no
C1 C6 . . 1.389(2) no
C1 C11 . . 1.520(3) no
C2 C3 . . 1.384(3) no
C3 C4 . . 1.379(2) no
C4 C5 . . 1.376(3) no
C5 C6 . . 1.380(3) no
C2 H2 . . 0.9300 no
C4 H4 . . 0.9300 no
C6 H6 . . 0.9300 no
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
N1A H11A O11 1_455 0.947(18) 1.925(18) 2.822(2) 157.4(15) yes
N1A H12A O12 . 0.96(2) 1.74(2) 2.696(2) 173(2) yes
N41A H41A O51 2_765 0.87(2) 2.37(2) 3.141(2) 147.5(18) yes
N41A H42A O41A 2_575 0.89(2) 1.99(2) 2.877(2) 175.8(17) 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6A N1A C2A C3A . . . . -58.9(2) no
C2A N1A C6A C5A . . . . 58.87(19) no
O31 N3 C3 C2 . . . . 2.1(2) no
O31 N3 C3 C4 . . . . -174.46(16) no
O32 N3 C3 C2 . . . . -178.67(16) no
O32 N3 C3 C4 . . . . 4.8(2) no
O52 N5 C5 C4 . . . . 168.85(16) no
O52 N5 C5 C6 . . . . -8.8(2) no
O51 N5 C5 C6 . . . . 170.81(15) no
O51 N5 C5 C4 . . . . -11.6(2) no
N1A C2A C3A C4A . . . . 56.79(19) no
C2A C3A C4A C5A . . . . -55.30(18) no
C2A C3A C4A C41A . . . . -178.92(14) no
C41A C4A C5A C6A . . . . 178.08(15) no
C3A C4A C41A O41A . . . . 95.34(18) no
C3A C4A C41A N41A . . . . -83.34(19) no
C5A C4A C41A O41A . . . . -27.3(2) no
C5A C4A C41A N41A . . . . 153.99(16) no
C3A C4A C5A C6A . . . . 55.18(19) no
C4A C5A C6A N1A . . . . -56.93(19) no
C6 C1 C2 C3 . . . . 0.9(2) no
C11 C1 C2 C3 . . . . 178.26(15) no
C2 C1 C6 C5 . . . . -0.6(2) no
C11 C1 C6 C5 . . . . -177.95(15) no
C2 C1 C11 O11 . . . . 175.83(15) no
C2 C1 C11 O12 . . . . -4.5(2) no
C6 C1 C11 O11 . . . . -6.8(2) no
C6 C1 C11 O12 . . . . 172.89(15) no
C1 C2 C3 N3 . . . . -176.96(14) no
C1 C2 C3 C4 . . . . -0.6(2) no
N3 C3 C4 C5 . . . . 176.32(15) no
C2 C3 C4 C5 . . . . -0.1(2) no
C3 C4 C5 N5 . . . . -177.09(15) no
C3 C4 C5 C6 . . . . 0.4(3) no
N5 C5 C6 C1 . . . . 177.41(14) no
C4 C5 C6 C1 . . . . -0.1(3) no
