##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1034875'
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Piperidinium 4-nitrophenolate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C5 H12 N +, C6 H4 N O3 -'
_chemical_formula_sum     'C11 H16 N2 O3'
_chemical_formula_iupac     'C5 H12 N +, C6 H4 N O3 -'
_chemical_formula_weight     224.26
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     6.867(5)
_cell_length_b     10.121(4)
_cell_length_c     16.497(6)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1146.6(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     658
_cell_measurement_theta_min     2.4
_cell_measurement_theta_max     28.6
_cell_measurement_temperature     295(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.26
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.299
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     480
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_absorpt_correction_T_min     0.9756
_exptl_absorpt_correction_T_max     0.9812
_exptl_special_details     ?
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker Kappa APEXII CCD'
_diffrn_measurement_method     'ω and φ scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6505
_diffrn_reflns_av_R_equivalents     0.0169
_diffrn_reflns_av_sigmaI/netI     0.0216
_diffrn_reflns_theta_min     2.36
_diffrn_reflns_theta_max     28.58
_diffrn_reflns_theta_full     28.58
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2908
_reflns_number_gt     2612
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0396
_refine_ls_R_factor_gt     0.0347
_refine_ls_wR_factor_gt     0.0877
_refine_ls_wR_factor_ref     0.0912
_refine_ls_goodness_of_fit_ref     1.041
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     2908
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0452P)²+0.1138P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.133
_refine_diff_density_min     -0.160
_refine_ls_extinction_method
;
SHELXL97 (Sheldrick, 2008)
;
_refine_ls_extinction_coef     0.119(6)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_cell_refinement
;
SAINT (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.08265(18) 0.22326(12) 0.09031(7) 0.0380(3) Uani d . 1 1 . .
    C C2 0.0102(2) 0.31257(12) 0.14583(7) 0.0404(3) Uani d . 1 1 . .
    H H2 -0.0220 0.2848 0.1979 0.049 Uiso calc R 1 1 . .
    C C3 -0.0144(2) 0.44223(12) 0.12419(7) 0.0403(3) Uani d . 1 1 . .
    H H3 -0.0638 0.5014 0.1621 0.048 Uiso calc R 1 1 . .
    C C4 0.03355(18) 0.48874(11) 0.04556(7) 0.0373(3) Uani d . 1 1 . .
    C C5 0.1115(2) 0.39408(13) -0.00839(8) 0.0474(3) Uani d . 1 1 . .
    H H5 0.1491 0.4211 -0.0600 0.057 Uiso calc R 1 1 . .
    C C6 0.1336(2) 0.26352(13) 0.01258(8) 0.0465(3) Uani d . 1 1 . .
    H H6 0.1820 0.2029 -0.0247 0.056 Uiso calc R 1 1 . .
    C C8 0.6387(2) 0.21154(17) 0.33603(10) 0.0570(4) Uani d . 1 1 . .
    H H8A 0.7057 0.2749 0.3702 0.068 Uiso calc R 1 1 . .
    H H8B 0.7348 0.1503 0.3149 0.068 Uiso calc R 1 1 . .
    C C9 0.5422(3) 0.28329(19) 0.26652(10) 0.0626(4) Uani d . 1 1 . .
    H H9A 0.6386 0.3342 0.2371 0.075 Uiso calc R 1 1 . .
    H H9B 0.4854 0.2197 0.2294 0.075 Uiso calc R 1 1 . .
    C C10 0.3854(3) 0.37423(16) 0.29817(10) 0.0545(4) Uani d . 1 1 . .
    H H10A 0.4442 0.4428 0.3312 0.065 Uiso calc R 1 1 . .
    H H10B 0.3199 0.4164 0.2530 0.065 Uiso calc R 1 1 . .
    C C11 0.2391(2) 0.29893(14) 0.34801(9) 0.0480(3) Uani d . 1 1 . .
    H H11A 0.1444 0.3601 0.3703 0.058 Uiso calc R 1 1 . .
    H H11B 0.1703 0.2370 0.3135 0.058 Uiso calc R 1 1 . .
    C C12 0.4907(2) 0.13639(13) 0.38617(9) 0.0488(3) Uani d . 1 1 . .
    H H12A 0.4341 0.0663 0.3537 0.059 Uiso calc R 1 1 . .
    H H12B 0.5549 0.0963 0.4324 0.059 Uiso calc R 1 1 . .
    N N1 0.10251(18) 0.08685(11) 0.11247(8) 0.0487(3) Uani d . 1 1 . .
    N N2 0.33415(17) 0.22610(10) 0.41493(6) 0.0405(3) Uani d . 1 1 . .
    H H2A 0.2438 0.1784 0.4415 0.049 Uiso calc R 1 1 . .
    H H2B 0.3851 0.2845 0.4502 0.049 Uiso calc R 1 1 . .
    O O1 0.00554(15) 0.61052(8) 0.02564(6) 0.0458(2) Uani d . 1 1 . .
    O O2 0.1387(2) 0.00445(11) 0.06015(8) 0.0730(4) Uani d . 1 1 . .
    O O3 0.0795(2) 0.05548(12) 0.18390(7) 0.0771(4) Uani d . 1 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . 1.3798(18) ?
    C1 C6 . 1.3902(18) ?
    C1 N1 . 1.4347(17) ?
    C2 C3 . 1.3703(18) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.4187(17) ?
    C3 H3 . 0.9300 ?
    C4 O1 . 1.2900(15) ?
    C4 C5 . 1.4129(18) ?
    C5 C6 . 1.374(2) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C8 C9 . 1.511(2) ?
    C8 C12 . 1.516(2) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 C10 . 1.510(2) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 C11 . 1.506(2) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 N2 . 1.4793(18) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 N2 . 1.4848(19) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    N1 O2 . 1.2257(17) ?
    N1 O3 . 1.2306(16) ?
    N2 H2A . 0.9000 ?
    N2 H2B . 0.9000 ?
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
    _geom_angle_publ_flag
    C2 C1 C6 . . 120.73(12) ?
    C2 C1 N1 . . 119.70(11) ?
    C6 C1 N1 . . 119.55(12) ?
    C3 C2 C1 . . 119.92(11) ?
    C3 C2 H2 . . 120.0 ?
    C1 C2 H2 . . 120.0 ?
    C2 C3 C4 . . 121.83(12) ?
    C2 C3 H3 . . 119.1 ?
    C4 C3 H3 . . 119.1 ?
    O1 C4 C5 . . 122.95(11) ?
    O1 C4 C3 . . 121.02(11) ?
    C5 C4 C3 . . 116.03(11) ?
    C6 C5 C4 . . 122.36(12) ?
    C6 C5 H5 . . 118.8 ?
    C4 C5 H5 . . 118.8 ?
    C5 C6 C1 . . 119.09(12) ?
    C5 C6 H6 . . 120.5 ?
    C1 C6 H6 . . 120.5 ?
    C9 C8 C12 . . 111.16(14) ?
    C9 C8 H8A . . 109.4 ?
    C12 C8 H8A . . 109.4 ?
    C9 C8 H8B . . 109.4 ?
    C12 C8 H8B . . 109.4 ?
    H8A C8 H8B . . 108.0 ?
    C10 C9 C8 . . 110.09(13) ?
    C10 C9 H9A . . 109.6 ?
    C8 C9 H9A . . 109.6 ?
    C10 C9 H9B . . 109.6 ?
    C8 C9 H9B . . 109.6 ?
    H9A C9 H9B . . 108.2 ?
    C11 C10 C9 . . 110.87(13) ?
    C11 C10 H10A . . 109.5 ?
    C9 C10 H10A . . 109.5 ?
    C11 C10 H10B . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 108.1 ?
    N2 C11 C10 . . 111.42(13) ?
    N2 C11 H11A . . 109.3 ?
    C10 C11 H11A . . 109.3 ?
    N2 C11 H11B . . 109.3 ?
    C10 C11 H11B . . 109.3 ?
    H11A C11 H11B . . 108.0 ?
    N2 C12 C8 . . 110.68(12) ?
    N2 C12 H12A . . 109.5 ?
    C8 C12 H12A . . 109.5 ?
    N2 C12 H12B . . 109.5 ?
    C8 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 108.1 ?
    O2 N1 O3 . . 121.66(13) ?
    O2 N1 C1 . . 119.64(12) ?
    O3 N1 C1 . . 118.70(12) ?
    C11 N2 C12 . . 112.69(11) ?
    C11 N2 H2A . . 109.1 ?
    C12 N2 H2A . . 109.1 ?
    C11 N2 H2B . . 109.1 ?
    C12 N2 H2B . . 109.1 ?
    H2A N2 H2B . . 107.8 ?
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
    C6 C1 C2 C3 . . . . 0.8(2) ?
    N1 C1 C2 C3 . . . . -178.12(12) ?
    C1 C2 C3 C4 . . . . -0.2(2) ?
    C2 C3 C4 O1 . . . . 178.45(13) ?
    C2 C3 C4 C5 . . . . -1.21(19) ?
    O1 C4 C5 C6 . . . . -177.44(14) ?
    C3 C4 C5 C6 . . . . 2.2(2) ?
    C4 C5 C6 C1 . . . . -1.8(2) ?
    C2 C1 C6 C5 . . . . 0.2(2) ?
    N1 C1 C6 C5 . . . . 179.09(14) ?
    C12 C8 C9 C10 . . . . 56.35(18) ?
    C8 C9 C10 C11 . . . . -56.27(19) ?
    C9 C10 C11 N2 . . . . 55.67(18) ?
    C9 C8 C12 N2 . . . . -55.31(17) ?
    C2 C1 N1 O2 . . . . 169.09(14) ?
    C6 C1 N1 O2 . . . . -9.8(2) ?
    C2 C1 N1 O3 . . . . -9.8(2) ?
    C6 C1 N1 O3 . . . . 171.33(14) ?
    C10 C11 N2 C12 . . . . -55.30(16) ?
    C8 C12 N2 C11 . . . . 54.81(16) ?
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
    N2 H2A O1 4_545 0.90 1.92 2.788(2) 161 y
    N2 H2B O1 2_565 0.90 1.80 2.6985(15) 175 y
    C6 H6 Cg1 3_555 0.93 2.75 3.428(3) 130 y
data_global
_journal_date_recd_electronic     2014-11-13
_journal_date_accepted     2014-11-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue     12
_journal_page_first     559
_journal_page_last     561
_journal_paper_category     GO
_journal_paper_doi     10.1107/S1600536814025306
_journal_coeditor_code     SU5022
_publ_contact_author_name     'G. Chakkaravarthi'
_publ_contact_author_address
;
Department of Physics
CPCL Polytechnic College
Chennai 600 068
India
;
_publ_contact_author_email
                             'chakkaravarthi_2005@yahoo.com,mohan66@hotmail.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '09940334668'
_publ_section_title
;
Crystal structure of piperidinium 4-nitrophenolate
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_address
    'N. Swarna Sowmya'
;
Department of Applied Physics,
Sri Venkateswara College of Engineering,
Chennai 602 117,
India
;
    'S. Sampathkrishnan'
;
Department of Applied Physics,
Sri Venkateswara College of Engineering,
Chennai 602 117,
India
;
    'S. Sudhahar'
;
Department of Physics,
Presidency College,
Chennai 600 005,
India
;
    'G. Chakkaravarthi'
;
Department of Physics,
CPCL Polytechnic College,
Chennai 600 068,
India
;
    'R. Mohan Kumar'
;
Department of Physics,
Presidency College,
Chennai 600 005,
India
;
_publ_section_synopsis
;
In the title salt, the piperidine ring of the cation adopts a chair
conformation. In the crystal, N---H...O hydrogen bonds link adjacent anions
and cations into infinite chains along [100]. The chains are linked by
C---H...π interactions, forming sheets lying parallel to (001).
;
