#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/86/2228665.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_2228665
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
_publ_section_title
;
 4-Carbamoylpiperidinium 5-nitrosalicylate
;
_journal_coeditor_code           BT5426
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o122
_journal_paper_doi               10.1107/S1600536810050129
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C6 H13 N2 O +, C7 H4 N O5 -'
_chemical_formula_moiety         'C6 H13 N2 O +, C7 H4 N O5 -'
_chemical_formula_sum            'C13 H17 N3 O6'
_chemical_formula_weight         311.30
_chemical_melting_point          463
_chemical_name_common            'isonipecotamide 5-nitrosalicylate'
_chemical_name_systematic
;
4-carbamoylpiperidine 2-hydroxy-5-nitrobenzoate
;
_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                 91.466(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0442(10)
_cell_length_b                   5.5851(3)
_cell_length_c                   17.1939(10)
_cell_measurement_reflns_used    3270
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.74
_cell_measurement_theta_min      3.55
_cell_volume                     1444.22(15)
_computing_cell_refinement
'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection
'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction
'CrysAlis PRO (Oxford Diffraction, 2010)'
_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_detector_area_resol_mean 16.077
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-S CCD-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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9191
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0402
_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)+(0.0486P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                1850
_reflns_number_total             2833
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5426.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228665
_cod_database_fobs_code          2228665
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 0.44900(9) 0.0250(2) 0.90133(7) 0.0575(5) Uani . . 1.000
N N1A 0.39663(10) 0.5656(3) 0.69549(9) 0.0452(6) Uani . . 1.000
N N41A 0.54984(11) 0.2658(4) 0.96084(10) 0.0480(6) Uani . . 1.000
C C2A 0.49383(12) 0.5253(3) 0.70538(12) 0.0545(7) Uani . . 1.000
C C3A 0.51390(12) 0.3391(3) 0.76686(10) 0.0516(7) Uani . . 1.000
C C4A 0.47324(11) 0.4101(3) 0.84420(9) 0.0423(6) Uani . . 1.000
C C5A 0.37359(11) 0.4529(3) 0.83207(10) 0.0451(6) Uani . . 1.000
C C6A 0.35478(11) 0.6369(3) 0.76956(10) 0.0463(6) Uani . . 1.000
C C41A 0.48930(12) 0.2177(3) 0.90488(10) 0.0435(6) Uani . . 1.000
O O2 0.40541(10) -0.1530(2) 0.42604(8) 0.0605(5) Uani . . 1.000
O O11 0.32739(8) 0.1529(2) 0.63160(7) 0.0507(4) Uani . . 1.000
O O12 0.39253(9) -0.1469(3) 0.57010(7) 0.0600(5) Uani . . 1.000
O O51 0.16400(10) 0.7176(3) 0.34253(8) 0.0729(6) Uani . . 1.000
O O52 0.17024(9) 0.7584(2) 0.46713(8) 0.0562(5) Uani . . 1.000
N N5 0.19077(10) 0.6528(3) 0.40756(9) 0.0510(6) Uani . . 1.000
C C1 0.32654(11) 0.1565(3) 0.49283(9) 0.0388(6) Uani . . 1.000
C C2 0.35489(12) 0.0445(3) 0.42422(10) 0.0460(6) Uani . . 1.000
C C3 0.32936(13) 0.1368(4) 0.35198(10) 0.0550(7) Uani . . 1.000
C C4 0.27649(13) 0.3354(4) 0.34625(10) 0.0529(7) Uani . . 1.000
C C5 0.24816(11) 0.4452(3) 0.41392(9) 0.0423(6) Uani . . 1.000
C C6 0.27300(11) 0.3580(3) 0.48665(9) 0.0396(6) Uani . . 1.000
C C11 0.35061(12) 0.0510(3) 0.57113(10) 0.0443(6) Uani . . 1.000
H H4A 0.50110 0.55900 0.86250 0.0510 Uiso calc R 1.000
H H11A 0.3874(12) 0.689(4) 0.6540(12) 0.065(6) Uiso . . 1.000
H H12A 0.3699(12) 0.422(4) 0.6763(11) 0.063(6) Uiso . . 1.000
H H21A 0.52260 0.67460 0.72000 0.0650 Uiso calc R 1.000
H H22A 0.51770 0.47330 0.65630 0.0650 Uiso calc R 1.000
H H31A 0.57780 0.32230 0.77390 0.0620 Uiso calc R 1.000
H H32A 0.49000 0.18580 0.75010 0.0620 Uiso calc R 1.000
H H41A 0.5753(13) 0.398(4) 0.9620(11) 0.054(7) Uiso . . 1.000
H H42A 0.5568(13) 0.147(4) 1.0029(12) 0.075(7) Uiso . . 1.000
H H51A 0.34480 0.30340 0.81770 0.0540 Uiso calc R 1.000
H H52A 0.34870 0.50710 0.88050 0.0540 Uiso calc R 1.000
H H61A 0.29100 0.65250 0.76110 0.0560 Uiso calc R 1.000
H H62A 0.37790 0.79110 0.78630 0.0560 Uiso calc R 1.000
H H2 0.4119(15) -0.184(4) 0.4809(14) 0.109(9) Uiso . . 1.000
H H3 0.34850 0.06260 0.30700 0.0660 Uiso calc R 1.000
H H4 0.25970 0.39640 0.29770 0.0630 Uiso calc R 1.000
H H6 0.25380 0.43450 0.53130 0.0470 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
C2 O2 H2 . . . 102.4(13) no
C2A N1A C6A . . . 112.29(14) no
C2A N1A H12A . . . 108.5(12) no
C6A N1A H11A . . . 111.8(12) no
H11A N1A H12A . . . 106.5(17) no
C6A N1A H12A . . . 109.7(11) no
C2A N1A H11A . . . 107.8(11) no
H41A N41A H42A . . . 122.7(18) no
C41A N41A H42A . . . 116.8(12) no
C41A N41A H41A . . . 120.1(13) no
O51 N5 O52 . . . 122.14(16) no
O51 N5 C5 . . . 118.93(15) no
O52 N5 C5 . . . 118.93(14) no
N1A C2A C3A . . . 111.33(15) no
C2A C3A C4A . . . 110.68(14) no
C3A C4A C41A . . . 110.79(14) no
C5A C4A C41A . . . 110.14(14) no
C3A C4A C5A . . . 109.56(13) no
C4A C5A C6A . . . 111.69(14) no
N1A C6A C5A . . . 110.57(14) no
O41A C41A N41A . . . 122.38(17) no
N41A C41A C4A . . . 116.62(16) no
O41A C41A C4A . . . 120.99(15) no
N1A C2A H21A . . . 109.00 no
N1A C2A H22A . . . 109.00 no
C3A C2A H21A . . . 109.00 no
C3A C2A H22A . . . 109.00 no
H21A C2A H22A . . . 108.00 no
C2A C3A H32A . . . 110.00 no
C4A C3A H31A . . . 109.00 no
C2A C3A H31A . . . 110.00 no
C4A C3A H32A . . . 109.00 no
H31A C3A H32A . . . 108.00 no
C41A C4A H4A . . . 109.00 no
C5A C4A H4A . . . 109.00 no
C3A C4A H4A . . . 109.00 no
C4A C5A H52A . . . 109.00 no
C6A C5A H51A . . . 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
C5A C6A H61A . . . 110.00 no
C5A C6A H62A . . . 110.00 no
N1A C6A H61A . . . 109.00 no
N1A C6A H62A . . . 110.00 no
C2 C1 C11 . . . 120.22(15) no
C6 C1 C11 . . . 120.82(14) no
C2 C1 C6 . . . 118.90(15) no
O2 C2 C1 . . . 121.94(15) no
O2 C2 C3 . . . 118.03(16) no
C1 C2 C3 . . . 120.02(16) no
C2 C3 C4 . . . 120.82(17) no
C3 C4 C5 . . . 119.17(16) no
N5 C5 C6 . . . 119.77(14) no
C4 C5 C6 . . . 121.25(16) no
N5 C5 C4 . . . 118.98(15) no
C1 C6 C5 . . . 119.84(15) no
O11 C11 C1 . . . 120.16(15) no
O12 C11 C1 . . . 115.81(15) no
O11 C11 O12 . . . 123.99(16) no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 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 . . 1.236(2) no
O2 C2 . . 1.340(2) no
O11 C11 . . 1.243(2) no
O12 C11 . . 1.273(2) no
O51 N5 . . 1.233(2) no
O52 N5 . . 1.228(2) no
O2 H2 . . 0.96(2) no
N1A C6A . . 1.489(2) no
N1A C2A . . 1.485(2) no
N41A C41A . . 1.335(2) no
N1A H12A . . 0.95(2) no
N1A H11A . . 1.00(2) no
N41A H41A . . 0.83(2) no
N41A H42A . . 0.99(2) no
N5 C5 . . 1.448(2) no
C2A C3A . . 1.508(3) no
C3A C4A . . 1.530(2) no
C4A C5A . . 1.527(2) no
C4A C41A . . 1.513(2) no
C5A C6A . . 1.509(2) no
C2A H22A . . 0.9700 no
C2A H21A . . 0.9700 no
C3A H31A . . 0.9700 no
C3A H32A . . 0.9700 no
C4A H4A . . 0.9800 no
C5A H51A . . 0.9700 no
C5A H52A . . 0.9700 no
C6A H62A . . 0.9700 no
C6A H61A . . 0.9700 no
C1 C6 . . 1.386(2) no
C1 C11 . . 1.505(2) no
C1 C2 . . 1.411(2) no
C2 C3 . . 1.390(3) no
C3 C4 . . 1.367(3) no
C4 C5 . . 1.392(2) no
C5 C6 . . 1.385(2) no
C3 H3 . . 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 O12 1_565 1.00(2) 1.71(2) 2.688(2) 164.2(18) yes
N1A H12A O11 . 0.95(2) 1.80(2) 2.747(2) 173.9(17) yes
N41A H41A O52 4_565 0.83(2) 2.39(2) 3.216(2) 170.8(19) yes
N41A H42A O41A 3_657 0.99(2) 1.91(2) 2.873(2) 164.8(18) yes
O2 H2 O12 . 0.96(2) 1.58(2) 2.4897(18) 156(2) yes
C2A H22A O2 3_656 0.97 2.57 3.450(2) 150 no
C6A H61A O11 2_556 0.97 2.60 3.263(2) 126 no
C6A H62A O41A 1_565 0.97 2.58 3.417(2) 145 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 . . . . 56.83(19) no
C2A N1A C6A C5A . . . . -56.01(18) no
O51 N5 C5 C4 . . . . 4.5(2) no
O51 N5 C5 C6 . . . . -174.74(16) no
O52 N5 C5 C4 . . . . -175.57(16) no
O52 N5 C5 C6 . . . . 5.2(2) no
N1A C2A C3A C4A . . . . -56.37(19) no
C2A C3A C4A C5A . . . . 55.43(18) no
C2A C3A C4A C41A . . . . 177.15(14) no
C5A C4A C41A O41A . . . . 49.2(2) no
C5A C4A C41A N41A . . . . -132.02(17) no
C3A C4A C41A O41A . . . . -72.2(2) no
C3A C4A C5A C6A . . . . -55.62(18) no
C41A C4A C5A C6A . . . . -177.72(14) no
C3A C4A C41A N41A . . . . 106.61(18) no
C4A C5A C6A N1A . . . . 55.72(18) no
C6 C1 C2 O2 . . . . -178.84(16) no
C6 C1 C2 C3 . . . . 0.2(3) no
C11 C1 C2 O2 . . . . -1.8(3) no
C11 C1 C2 C3 . . . . 177.28(17) no
C2 C1 C6 C5 . . . . 0.2(2) no
C11 C1 C6 C5 . . . . -176.88(16) no
C2 C1 C11 O11 . . . . 178.30(16) no
C2 C1 C11 O12 . . . . -3.8(2) no
C6 C1 C11 O11 . . . . -4.7(3) no
C6 C1 C11 O12 . . . . 173.26(16) no
O2 C2 C3 C4 . . . . 178.81(18) no
C1 C2 C3 C4 . . . . -0.3(3) no
C2 C3 C4 C5 . . . . 0.0(3) no
C3 C4 C5 N5 . . . . -178.83(17) no
C3 C4 C5 C6 . . . . 0.4(3) no
N5 C5 C6 C1 . . . . 178.76(15) no
C4 C5 C6 C1 . . . . -0.5(3) no
