#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/39/2233911.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_2233911
loop_
_publ_author_name
'Fan, Ping'
'Ge, Chunhua'
'Sun, Mingjun'
'Li, Weiwei'
'Shang, Runshan'
_publ_section_title
;
 2-(4-Carboxypiperidinium-1-yl)pyridine-3-carboxylate
;
_journal_coeditor_code           KP2382
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o913
_journal_paper_doi               10.1107/S1600536812005752
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C12 H14 N2 O4'
_chemical_formula_moiety         'C12 H14 N2 O4'
_chemical_formula_sum            'C12 H14 N2 O4'
_chemical_formula_weight         250.25
_chemical_name_systematic
;
2-(4-Carboxypiperidinium-1-yl)pyridine-3-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.57(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1094(14)
_cell_length_b                   18.667(4)
_cell_length_c                   8.6603(17)
_cell_measurement_reflns_used    361
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.65
_cell_measurement_theta_min      2.53
_cell_volume                     1147.1(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6010
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.338
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0685P)²+0.1385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1184
_reflns_number_gt                1841
_reflns_number_total             2237
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2382.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233911
_cod_database_fobs_code          2233911
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O4 0.06398(16) 0.42630(6) 0.56128(13) 0.0431(3) Uani d . 1 1
N N2 0.41209(16) 0.63507(6) 0.81715(14) 0.0291(3) Uani d . 1 1
O O3 -0.10491(16) 0.44848(6) 0.76521(13) 0.0445(3) Uani d . 1 1
H H3 -0.1719 0.4164 0.7277 0.067 Uiso calc R 1 1
N N1 0.68999(17) 0.64666(6) 0.98026(15) 0.0373(3) Uani d . 1 1
O O2 0.26774(16) 0.75408(6) 0.70841(13) 0.0466(3) Uani d . 1 1
C C3 0.55581(18) 0.68088(7) 0.89789(16) 0.0278(3) Uani d . 1 1
C C8 0.1114(2) 0.56996(8) 0.83901(18) 0.0355(4) Uani d . 1 1
H H8A 0.0488 0.6001 0.7604 0.043 Uiso calc R 1 1
H H8B 0.0187 0.5552 0.9102 0.043 Uiso calc R 1 1
C C12 0.0444(2) 0.45637(7) 0.68272(17) 0.0314(3) Uani d . 1 1
O O1 0.36031(17) 0.85729(6) 0.82086(15) 0.0534(4) Uani d . 1 1
C C7 0.2667(2) 0.61218(8) 0.92594(17) 0.0357(4) Uani d . 1 1
H H7A 0.2134 0.6541 0.9730 0.043 Uiso calc R 1 1
H H7B 0.3256 0.5828 1.0077 0.043 Uiso calc R 1 1
C C9 0.19275(19) 0.50397(7) 0.76289(16) 0.0301(3) Uani d . 1 1
H H9 0.2557 0.4754 0.8458 0.036 Uiso calc R 1 1
C C10 0.3436(2) 0.52666(8) 0.65609(17) 0.0376(4) Uani d . 1 1
H H10A 0.4004 0.4843 0.6136 0.045 Uiso calc R 1 1
H H10B 0.2858 0.5541 0.5707 0.045 Uiso calc R 1 1
C C2 0.53838(18) 0.75479(7) 0.88389(16) 0.0288(3) Uani d . 1 1
C C11 0.4954(2) 0.57139(8) 0.74008(19) 0.0369(4) Uani d . 1 1
H H11A 0.5636 0.5422 0.8174 0.044 Uiso calc R 1 1
H H11B 0.5842 0.5877 0.6670 0.044 Uiso calc R 1 1
C C1 0.3745(2) 0.79174(8) 0.79697(18) 0.0352(4) Uani d . 1 1
C C5 0.8281(2) 0.76099(9) 1.03995(19) 0.0411(4) Uani d . 1 1
H H5 0.9268 0.7873 1.0871 0.049 Uiso calc R 1 1
C C6 0.6822(2) 0.79468(8) 0.95705(18) 0.0358(4) Uani d . 1 1
H H6 0.6801 0.8444 0.9501 0.043 Uiso calc R 1 1
C C4 0.8245(2) 0.68742(9) 1.05140(19) 0.0402(4) Uani d . 1 1
H H4 0.9201 0.6649 1.1114 0.048 Uiso calc R 1 1
H H2A 0.344(3) 0.6686(11) 0.742(2) 0.063(6) Uiso d . 1 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
C3 N2 C11 112.86(11)
C3 N2 C7 110.53(11)
C11 N2 C7 111.03(11)
C3 N2 H2A 103.8(11)
C11 N2 H2A 113.0(11)
C7 N2 H2A 105.2(11)
C12 O3 H3 109.5
C3 N1 C4 116.38(13)
N1 C3 C2 125.81(13)
N1 C3 N2 115.57(12)
C2 C3 N2 118.61(12)
C7 C8 C9 110.46(12)
C7 C8 H8A 109.6
C9 C8 H8A 109.6
C7 C8 H8B 109.6
C9 C8 H8B 109.6
H8A C8 H8B 108.1
O4 C12 O3 123.91(14)
O4 C12 C9 123.86(13)
O3 C12 C9 112.14(12)
N2 C7 C8 110.12(12)
N2 C7 H7A 109.6
C8 C7 H7A 109.6
N2 C7 H7B 109.6
C8 C7 H7B 109.6
H7A C7 H7B 108.1
C12 C9 C10 112.48(11)
C12 C9 C8 113.54(12)
C10 C9 C8 109.78(11)
C12 C9 H9 106.9
C10 C9 H9 106.9
C8 C9 H9 106.9
C11 C10 C9 111.73(12)
C11 C10 H10A 109.3
C9 C10 H10A 109.3
C11 C10 H10B 109.3
C9 C10 H10B 109.3
H10A C10 H10B 107.9
C6 C2 C3 115.73(13)
C6 C2 C1 120.38(12)
C3 C2 C1 123.88(13)
N2 C11 C10 111.12(12)
N2 C11 H11A 109.4
C10 C11 H11A 109.4
N2 C11 H11B 109.4
C10 C11 H11B 109.4
H11A C11 H11B 108.0
O1 C1 O2 126.68(14)
O1 C1 C2 115.64(13)
O2 C1 C2 117.68(12)
C6 C5 C4 118.46(14)
C6 C5 H5 120.8
C4 C5 H5 120.8
C5 C6 C2 120.24(14)
C5 C6 H6 119.9
C2 C6 H6 119.9
N1 C4 C5 123.25(14)
N1 C4 H4 118.4
C5 C4 H4 118.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C12 1.2079(18)
N2 C3 1.4749(17)
N2 C11 1.5030(18)
N2 C7 1.5031(18)
N2 H2A 1.01(2)
O3 C12 1.3240(18)
O3 H3 0.8200
N1 C3 1.3200(18)
N1 C4 1.342(2)
O2 C1 1.2593(18)
C3 C2 1.3897(19)
C8 C7 1.518(2)
C8 C9 1.528(2)
C8 H8A 0.9700
C8 H8B 0.9700
C12 C9 1.5142(19)
O1 C1 1.2462(18)
C7 H7A 0.9700
C7 H7B 0.9700
C9 C10 1.519(2)
C9 H9 0.9800
C10 C11 1.515(2)
C10 H10A 0.9700
C10 H10B 0.9700
C2 C6 1.386(2)
C2 C1 1.514(2)
C11 H11A 0.9700
C11 H11B 0.9700
C5 C6 1.376(2)
C5 C4 1.377(2)
C5 H5 0.9300
C6 H6 0.9300
C4 H4 0.9300
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
O3 H3 O1 2_546 0.82 1.77 2.566(2) 166 yes
N2 H2A O2 1_555 1.01(2) 1.71(2) 2.599(2) 146.0(16) yes
