#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/78/2017888.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_2017888
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
_publ_section_title
;
 Anhydrous 1:1 proton-transfer compounds of isonipecotamide with picric
 acid and 3,5-dinitrosalicylic acid: 4-carbamoylpiperidinium
 2,4,6-trinitrophenolate and two polymorphs of 4-carbamoylpiperidinium
 2-carboxy-4,6-dinitrophenolate
;
_journal_coeditor_code           FG3206
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o609
_journal_page_last               o613
_journal_paper_doi               10.1107/S010827011004672X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H13 N2 O +, C7 H3 N2 O7 -'
_chemical_formula_moiety         'C6 H13 N2 O +, C7 H3 N2 O7 -'
_chemical_formula_sum            'C13 H16 N4 O8'
_chemical_formula_weight         356.30
_chemical_melting_point          475
_chemical_name_common
'isonipecotamide 3,5-dinitrosalicylate (polymorph 1)'
_chemical_name_systematic
;
4-carbamoylpiperidinium 2-carboxy-4,6-dinitrophenolate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 118.196(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7131(12)
_cell_length_b                   12.6450(11)
_cell_length_c                   11.8521(14)
_cell_measurement_reflns_used    5903
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.90
_cell_measurement_theta_min      3.09
_cell_volume                     1547.1(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S Ultra CCD-detector diffractometer'
_diffrn_measurement_method       'ω scans'
_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  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19733
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0388
_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)+(0.0505P)²+0.3254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0983
_reflns_number_gt                2456
_reflns_number_total             3048
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg3206.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017888
_cod_database_fobs_code          2017888
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x+1/2, -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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O41A 0.91435(11) 0.16355(8) 0.34281(12) 0.0376(4) Uani . . 1.000
N N1A 0.64157(13) 0.46323(12) 0.24420(14) 0.0302(4) Uani . . 1.000
N N41A 1.07432(14) 0.25715(14) 0.33428(14) 0.0326(5) Uani . . 1.000
C C2A 0.66526(17) 0.43037(14) 0.13574(16) 0.0389(6) Uani . . 1.000
C C3A 0.74700(16) 0.33094(13) 0.16879(16) 0.0356(5) Uani . . 1.000
C C4A 0.87494(14) 0.34730(11) 0.29070(15) 0.0251(5) Uani . . 1.000
C C5A 0.84626(16) 0.37753(14) 0.40008(16) 0.0344(5) Uani . . 1.000
C C6A 0.76398(16) 0.47717(14) 0.36640(16) 0.0350(5) Uani . . 1.000
C C41A 0.95693(14) 0.24793(12) 0.32469(14) 0.0257(5) Uani . . 1.000
O O2 0.47303(10) 0.29794(9) 0.22748(12) 0.0371(4) Uani . . 1.000
O O11 0.37954(11) -0.01363(9) 0.21453(13) 0.0417(4) Uani . . 1.000
O O12 0.53269(11) 0.10794(10) 0.26508(12) 0.0405(4) Uani . . 1.000
O O31 0.37968(13) 0.49662(10) 0.18436(18) 0.0641(6) Uani . . 1.000
O O32 0.18116(14) 0.51899(10) 0.04687(15) 0.0565(5) Uani . . 1.000
O O51 -0.13172(11) 0.24904(11) -0.05034(14) 0.0496(4) Uani . . 1.000
O O52 -0.07272(12) 0.09399(11) 0.03421(15) 0.0569(5) Uani . . 1.000
N N3 0.27091(14) 0.46176(11) 0.11677(15) 0.0344(5) Uani . . 1.000
N N5 -0.04816(12) 0.18363(11) 0.01234(14) 0.0342(5) Uani . . 1.000
C C1 0.31189(14) 0.16553(11) 0.17075(14) 0.0240(5) Uani . . 1.000
C C2 0.35196(14) 0.27440(12) 0.17692(14) 0.0252(5) Uani . . 1.000
C C3 0.24707(15) 0.34884(11) 0.12059(15) 0.0256(5) Uani . . 1.000
C C4 0.11787(14) 0.31943(12) 0.06519(15) 0.0265(5) Uani . . 1.000
C C5 0.08755(14) 0.21438(12) 0.06551(15) 0.0259(4) Uani . . 1.000
C C6 0.18314(14) 0.13709(12) 0.11806(14) 0.0251(5) Uani . . 1.000
C C11 0.41058(15) 0.07888(12) 0.21983(15) 0.0283(5) Uani . . 1.000
H H4A 0.92350 0.40640 0.27660 0.0300 Uiso calc R 1.000
H H11A 0.591(2) 0.4179(17) 0.2527(19) 0.049(6) Uiso . . 1.000
H H12A 0.5991(18) 0.5283(15) 0.2205(17) 0.040(5) Uiso . . 1.000
H H21A 0.71010 0.48810 0.11600 0.0470 Uiso calc R 1.000
H H22A 0.58130 0.41750 0.05860 0.0470 Uiso calc R 1.000
H H31A 0.76450 0.31250 0.09720 0.0430 Uiso calc R 1.000
H H32A 0.69900 0.27150 0.18120 0.0430 Uiso calc R 1.000
H H41A 1.1000(17) 0.3199(16) 0.3247(17) 0.035(5) Uiso . . 1.000
H H42A 1.120(2) 0.2035(18) 0.3522(19) 0.048(6) Uiso . . 1.000
H H51A 0.79990 0.31880 0.41610 0.0410 Uiso calc R 1.000
H H52A 0.92870 0.38960 0.47930 0.0410 Uiso calc R 1.000
H H61A 0.74310 0.49380 0.43620 0.0420 Uiso calc R 1.000
H H62A 0.81360 0.53730 0.35790 0.0420 Uiso calc R 1.000
H H4 0.05130 0.37100 0.02760 0.0320 Uiso calc R 1.000
H H6 0.15980 0.06510 0.11760 0.0300 Uiso calc R 1.000
H H12 0.53160 0.18860 0.2602 0.0490 Uiso . 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
C11 O12 H12 . . . 106.00 no
C2A N1A C6A . . . 112.57(15) no
H11A N1A H12A . . . 109(2) no
C6A N1A H11A . . . 111.3(14) no
C2A N1A H11A . . . 109.4(14) no
C2A N1A H12A . . . 106.0(12) no
C6A N1A H12A . . . 108.6(12) no
H41A N41A H42A . . . 124(2) no
C41A N41A H41A . . . 118.3(14) no
C41A N41A H42A . . . 117.9(17) no
O32 N3 C3 . . . 118.99(16) no
O31 N3 C3 . . . 119.19(15) no
O31 N3 O32 . . . 121.82(15) no
O51 N5 C5 . . . 118.44(14) no
O52 N5 C5 . . . 118.12(15) no
O51 N5 O52 . . . 123.43(17) no
N1A C2A C3A . . . 111.06(14) no
C2A C3A C4A . . . 110.49(13) no
C5A C4A C41A . . . 110.26(13) no
C3A C4A C5A . . . 108.95(15) no
C3A C4A C41A . . . 110.77(12) no
C4A C5A C6A . . . 110.46(14) no
N1A C6A C5A . . . 110.88(14) no
O41A C41A C4A . . . 120.24(16) no
N41A C41A C4A . . . 116.72(15) no
O41A C41A N41A . . . 123.04(16) no
C3A C2A H22A . . . 109.00 no
N1A C2A H22A . . . 109.00 no
C3A C2A H21A . . . 109.00 no
H21A C2A H22A . . . 108.00 no
N1A C2A H21A . . . 109.00 no
C4A C3A H31A . . . 110.00 no
C2A C3A H32A . . . 110.00 no
H31A C3A H32A . . . 108.00 no
C2A C3A H31A . . . 110.00 no
C4A C3A H32A . . . 110.00 no
C41A C4A H4A . . . 109.00 no
C3A C4A H4A . . . 109.00 no
C5A C4A H4A . . . 109.00 no
C4A C5A H52A . . . 110.00 no
C4A C5A H51A . . . 110.00 no
C6A C5A H51A . . . 110.00 no
C6A C5A H52A . . . 110.00 no
H51A C5A H52A . . . 108.00 no
H61A C6A H62A . . . 108.00 no
N1A C6A H62A . . . 109.00 no
C5A C6A H61A . . . 109.00 no
N1A C6A H61A . . . 109.00 no
C5A C6A H62A . . . 109.00 no
C2 C1 C6 . . . 122.05(15) no
C2 C1 C11 . . . 120.33(15) no
C6 C1 C11 . . . 117.61(13) no
O2 C2 C3 . . . 125.23(14) no
C1 C2 C3 . . . 114.49(15) no
O2 C2 C1 . . . 120.27(15) no
N3 C3 C2 . . . 121.40(16) no
C2 C3 C4 . . . 123.14(14) no
N3 C3 C4 . . . 115.46(15) no
C3 C4 C5 . . . 118.91(15) no
N5 C5 C6 . . . 119.21(14) no
C4 C5 C6 . . . 121.68(16) no
N5 C5 C4 . . . 119.09(15) no
C1 C6 C5 . . . 119.71(14) no
O11 C11 C1 . . . 121.76(17) no
O12 C11 C1 . . . 116.34(14) no
O11 C11 O12 . . . 121.87(16) no
C3 C4 H4 . . . 121.00 no
C5 C4 H4 . . . 121.00 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 . . 1.239(2) no
O2 C2 . . 1.287(2) no
O11 C11 . . 1.218(2) no
O12 C11 . . 1.320(2) no
O31 N3 . . 1.223(2) no
O32 N3 . . 1.222(2) no
O51 N5 . . 1.228(2) no
O52 N5 . . 1.227(2) no
O12 H12 . . 1.01 no
N1A C6A . . 1.491(2) no
N1A C2A . . 1.496(2) no
N41A C41A . . 1.330(3) no
N1A H12A . . 0.93(2) no
N1A H11A . . 0.86(2) no
N41A H42A . . 0.83(2) no
N41A H41A . . 0.88(2) no
N3 C3 . . 1.460(2) no
N5 C5 . . 1.459(2) no
C2A C3A . . 1.515(3) no
C3A C4A . . 1.527(2) no
C4A C5A . . 1.533(2) no
C4A C41A . . 1.516(2) no
C5A C6A . . 1.521(3) no
C2A H22A . . 0.9900 no
C2A H21A . . 0.9900 no
C3A H32A . . 0.9900 no
C3A H31A . . 0.9900 no
C4A H4A . . 1.0000 no
C5A H51A . . 0.9900 no
C5A H52A . . 0.9900 no
C6A H61A . . 0.9900 no
C6A H62A . . 0.9900 no
C1 C6 . . 1.380(2) no
C1 C11 . . 1.497(2) no
C1 C2 . . 1.445(2) no
C2 C3 . . 1.437(2) no
C3 C4 . . 1.386(3) no
C4 C5 . . 1.376(2) no
C5 C6 . . 1.392(2) no
C4 H4 . . 0.9500 no
C6 H6 . . 0.9500 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 O2 . 0.86(2) 1.98(2) 2.817(2) 164(2) yes
N1A H11A O31 . 0.86(2) 2.43(2) 2.835(3) 109.7(17) yes
N1A H12A O31 . 0.93(2) 2.43(2) 2.835(3) 106.1(15) yes
N1A H12A O41A 2_655 0.93(2) 1.844(19) 2.6964(19) 151(2) yes
N41A H41A O11 2_655 0.88(2) 2.19(2) 3.053(2) 168(2) yes
O12 H12 O2 . 1.01 1.52 2.4829(17) 157 yes
C4A H4A O11 2_655 1.00 2.48 3.396(2) 153 no
C6 H6 O52 3_555 0.95 2.57 3.356(2) 141 no
C6A H61A O52 2_555 0.99 2.52 3.329(3) 138 no
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 . . . . 55.3(2) no
C2A N1A C6A C5A . . . . -55.14(19) no
O31 N3 C3 C2 . . . . -15.0(3) no
O31 N3 C3 C4 . . . . 165.79(17) no
O32 N3 C3 C2 . . . . 165.64(17) no
O32 N3 C3 C4 . . . . -13.5(2) no
O52 N5 C5 C4 . . . . -166.78(16) no
O52 N5 C5 C6 . . . . 11.7(2) no
O51 N5 C5 C6 . . . . -169.32(15) no
O51 N5 C5 C4 . . . . 12.2(2) no
N1A C2A C3A C4A . . . . -56.8(2) no
C2A C3A C4A C5A . . . . 58.26(18) no
C2A C3A C4A C41A . . . . 179.72(15) no
C41A C4A C5A C6A . . . . -179.97(15) no
C3A C4A C41A O41A . . . . -58.1(2) no
C3A C4A C41A N41A . . . . 122.29(16) no
C5A C4A C41A O41A . . . . 62.58(19) no
C5A C4A C41A N41A . . . . -117.03(16) no
C3A C4A C5A C6A . . . . -58.22(18) no
C4A C5A C6A N1A . . . . 56.7(2) no
C6 C1 C2 O2 . . . . 179.58(15) no
C6 C1 C2 C3 . . . . -1.8(2) no
C11 C1 C2 O2 . . . . -1.7(2) no
C11 C1 C2 C3 . . . . 176.98(14) no
C2 C1 C6 C5 . . . . 1.9(2) no
C11 C1 C6 C5 . . . . -176.90(14) no
C2 C1 C11 O11 . . . . -179.15(16) no
C2 C1 C11 O12 . . . . -1.4(2) no
C6 C1 C11 O11 . . . . -0.4(2) no
C6 C1 C11 O12 . . . . 177.40(14) no
O2 C2 C3 N3 . . . . -0.3(3) no
O2 C2 C3 C4 . . . . 178.83(16) no
C1 C2 C3 N3 . . . . -178.86(15) no
C1 C2 C3 C4 . . . . 0.3(2) no
N3 C3 C4 C5 . . . . -179.72(15) no
C2 C3 C4 C5 . . . . 1.1(3) no
C3 C4 C5 N5 . . . . 177.34(15) no
C3 C4 C5 C6 . . . . -1.1(2) no
N5 C5 C6 C1 . . . . -178.80(14) no
C4 C5 C6 C1 . . . . -0.4(2) no
