#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/39/2223928.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_2223928
loop_
_publ_author_name
'Tseng, Feng-Shuen'
'Lin, Chia-Her'
_publ_section_title
;
 4,4'-Trimethylenedipiperidiniumbenzene-1,4-dicarboxylate
;
_journal_coeditor_code           NC2162
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2822
_journal_paper_doi               10.1107/S1600536809042901
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H28 N2 2+ , C8 H4 O4 2-'
_chemical_formula_moiety         'C13 H28 N2, C8 H4 O4'
_chemical_formula_sum            'C21 H32 N2 O4'
_chemical_formula_weight         376.49
_chemical_name_systematic
;
 4,4'-Trimethylenedipiperidiniumbenzene-1,4-dicarboxylate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 108.610(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.2902(18)
_cell_length_b                   8.4534(8)
_cell_length_c                   11.8815(9)
_cell_measurement_reflns_used    2292
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.128
_cell_measurement_theta_min      2.997
_cell_volume                     1931.4(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.1136
_diffrn_reflns_av_sigmaI/netI    0.1213
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9090
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.204
_refine_ls_extinction_coef       0.0026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.815
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.815
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0462
_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)+(0.0287P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0949
_reflns_number_gt                1073
_reflns_number_total             2286
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            nc2162.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2223928
_cod_database_fobs_code          2223928
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 -0.28726(7) 0.06898(17) -0.42869(12) 0.0323(4) Uani d . 1 . .
H H1N1 -0.3055 0.1498 -0.4782 0.039 Uiso calc R 1 . .
H H2N1 -0.2517 0.0285 -0.4493 0.039 Uiso calc R 1 . .
C C4 -0.38067(9) 0.0846(2) -0.28506(14) 0.0280(4) Uani d . 1 . .
H H4A -0.3658 -0.0015 -0.2272 0.034 Uiso calc R 1 . .
C C5 -0.44100(9) 0.1711(2) -0.26231(15) 0.0308(5) Uani d . 1 . .
H H5A -0.4226 0.2327 -0.1902 0.037 Uiso calc R 1 . .
H H5B -0.4601 0.2450 -0.3269 0.037 Uiso calc R 1 . .
C C7 -0.5000 0.0702(3) -0.2500 0.0322(7) Uani d S 1 . .
H H7A -0.4829 0.0036 -0.1814 0.039 Uiso d R 1 . .
C C8 -0.34100(9) -0.0545(2) -0.44141(16) 0.0343(5) Uani d . 1 . .
H H8A -0.3213 -0.1429 -0.3896 0.041 Uiso calc R 1 . .
H H8B -0.3569 -0.0929 -0.5226 0.041 Uiso calc R 1 . .
C C9 -0.26075(9) 0.1290(2) -0.30457(15) 0.0379(5) Uani d . 1 . .
H H9A -0.2259 0.2099 -0.2988 0.045 Uiso calc R 1 . .
H H9B -0.2390 0.0432 -0.2515 0.045 Uiso calc R 1 . .
C C10 -0.40175(9) 0.0137(2) -0.40950(15) 0.0310(5) Uani d . 1 . .
H H10A -0.4357 -0.0692 -0.4152 0.037 Uiso calc R 1 . .
H H10B -0.4238 0.0950 -0.4667 0.037 Uiso calc R 1 . .
C C13 -0.31977(9) 0.1974(2) -0.26785(16) 0.0354(5) Uani d . 1 . .
H H13A -0.3364 0.2927 -0.3136 0.042 Uiso calc R 1 . .
H H13B -0.3020 0.2274 -0.1848 0.042 Uiso calc R 1 . .
O O1 -0.13904(7) 0.19495(16) -0.41743(12) 0.0428(4) Uani d . 1 . .
O O2 -0.18035(7) -0.03599(17) -0.50059(12) 0.0522(4) Uani d . 1 . .
C C6 -0.06382(9) 0.0291(2) -0.48175(15) 0.0290(4) Uani d . 1 . .
C C11 -0.13273(10) 0.0646(2) -0.46455(16) 0.0346(5) Uani d . 1 . .
C C12 -0.05893(10) -0.0776(2) -0.56701(16) 0.0345(5) Uani d . 1 . .
H H12A -0.0986 -0.1304 -0.6131 0.041 Uiso calc R 1 . .
C C14 -0.00395(10) 0.1067(2) -0.41537(15) 0.0345(5) Uani d . 1 . .
H H14A -0.0062 0.1796 -0.3580 0.041 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 N1 C9 . . 111.26(13) ?
C8 N1 H1N1 . . 109.4 ?
C9 N1 H1N1 . . 109.4 ?
C8 N1 H2N1 . . 109.4 ?
C9 N1 H2N1 . . 109.4 ?
H1N1 N1 H2N1 . . 108.0 ?
C13 C4 C5 . . 109.83(14) ?
C13 C4 C10 . . 109.95(14) ?
C5 C4 C10 . . 111.61(14) ?
C13 C4 H4A . . 108.5 ?
C5 C4 H4A . . 108.5 ?
C10 C4 H4A . . 108.5 ?
C7 C5 C4 . . 116.86(15) ?
C7 C5 H5A . . 108.1 ?
C4 C5 H5A . . 108.1 ?
C7 C5 H5B . . 108.1 ?
C4 C5 H5B . . 108.1 ?
H5A C5 H5B . . 107.3 ?
C5 C7 C5 2_454 . 111.4(2) ?
C5 C7 H7A 2_454 . 109.3 ?
C5 C7 H7A . . 109.3 ?
N1 C8 C10 . . 109.74(15) ?
N1 C8 H8A . . 109.7 ?
C10 C8 H8A . . 109.7 ?
N1 C8 H8B . . 109.7 ?
C10 C8 H8B . . 109.7 ?
H8A C8 H8B . . 108.2 ?
N1 C9 C13 . . 110.28(14) ?
N1 C9 H9A . . 109.6 ?
C13 C9 H9A . . 109.6 ?
N1 C9 H9B . . 109.6 ?
C13 C9 H9B . . 109.6 ?
H9A C9 H9B . . 108.1 ?
C8 C10 C4 . . 113.16(14) ?
C8 C10 H10A . . 108.9 ?
C4 C10 H10A . . 108.9 ?
C8 C10 H10B . . 108.9 ?
C4 C10 H10B . . 108.9 ?
H10A C10 H10B . . 107.8 ?
C9 C13 C4 . . 113.86(15) ?
C9 C13 H13A . . 108.8 ?
C4 C13 H13A . . 108.8 ?
C9 C13 H13B . . 108.8 ?
C4 C13 H13B . . 108.8 ?
H13A C13 H13B . . 107.7 ?
C12 C6 C14 . . 118.11(16) ?
C12 C6 C11 . . 121.05(17) ?
C14 C6 C11 . . 120.80(17) ?
O2 C11 O1 . . 124.56(18) ?
O2 C11 C6 . . 117.75(18) ?
O1 C11 C6 . . 117.67(18) ?
C14 C12 C6 5_554 . 120.88(17) ?
C14 C12 H12A 5_554 . 119.6 ?
C6 C12 H12A . . 119.6 ?
C12 C14 C6 5_554 . 121.00(17) ?
C12 C14 H14A 5_554 . 119.5 ?
C6 C14 H14A . . 119.5 ?
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
N1 C8 . 1.482(2) ?
N1 C9 . 1.488(2) ?
N1 H1N1 . 0.9000 ?
N1 H2N1 . 0.9000 ?
C4 C13 . 1.522(2) ?
C4 C5 . 1.522(2) ?
C4 C10 . 1.525(2) ?
C4 H4A . 0.9800 ?
C5 C7 . 1.515(2) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C7 C5 2_454 1.514(2) ?
C7 H7A . 0.9598 ?
C8 C10 . 1.514(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C13 . 1.514(2) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
O1 C11 . 1.261(2) ?
O2 C11 . 1.255(2) ?
C6 C12 . 1.383(2) ?
C6 C14 . 1.384(2) ?
C6 C11 . 1.506(2) ?
C12 C14 5_554 1.379(2) ?
C12 H12A . 0.9300 ?
C14 C12 5_554 1.379(2) ?
C14 H14A . 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
N1 H1N1 O1 7_454 0.90 1.91 2.7958(19) 168.9
N1 H2N1 O2 . 0.90 1.82 2.7213(18) 174.2
N1 H2N1 O1 . 0.90 2.61 3.1528(19) 119.8
