#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/77/2017712.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_2017712
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
_publ_section_title
;
 Low-dimensional hydrogen-bonded structures in the 1:1 and 1:2
 proton-transfer compounds of 4,5-dichlorophthalic acid with the
 aliphatic Lewis bases triethylamine, diethylamine, n-butylamine
 and piperidine
;
_journal_coeditor_code           GD3347
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o374
_journal_page_last               o380
_journal_paper_doi               10.1107/S0108270110022328
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '2C5 H12 N +, C8 H2 Cl2 O4 2-, H2 O'
_chemical_formula_moiety         '2(C5 H12 N +), C8 H2 Cl2 O4 2-, H2 O'
_chemical_formula_sum            'C18 H28 Cl2 N2 O5'
_chemical_formula_weight         423.32
_chemical_melting_point          405
_chemical_name_common
'piperidinium 4,5-dichlorophthalate monohydrate'
_chemical_name_systematic
;
bis(piperidinium) 4,5-dichlorobenzene-1,2-dicarboxylate monohydrate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.903(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8481(10)
_cell_length_b                   10.5937(8)
_cell_length_c                   14.6129(10)
_cell_measurement_reflns_used    6842
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.76
_cell_measurement_theta_min      3.40
_cell_volume                     2111.8(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    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 16.077
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S 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  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26626
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.42
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0375
_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)+(0.0644P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1032
_reflns_number_gt                3570
_reflns_number_total             4805
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3347.cif
_cod_data_source_block           IV
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017712
_cod_database_fobs_code          2017712
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1A 0.06019(10) 0.62705(12) 0.30611(8) 0.0248(4) Uani . . 1.000
C C2A 0.08561(12) 0.59975(16) 0.40785(10) 0.0342(5) Uani . . 1.000
C C3A 0.19204(12) 0.55895(17) 0.43278(11) 0.0389(5) Uani . . 1.000
C C4A 0.21235(12) 0.44461(15) 0.37525(11) 0.0360(5) Uani . . 1.000
C C5A 0.18615(12) 0.47509(15) 0.27239(11) 0.0345(5) Uani . . 1.000
C C6A 0.07982(12) 0.51771(15) 0.24770(11) 0.0336(5) Uani . . 1.000
N N1B -0.18744(9) 0.53788(12) 0.07825(9) 0.0259(4) Uani . . 1.000
C C2B -0.17157(12) 0.47472(15) -0.00943(11) 0.0331(5) Uani . . 1.000
C C3B -0.25761(14) 0.39003(16) -0.04612(12) 0.0422(6) Uani . . 1.000
C C4B -0.35296(14) 0.46454(18) -0.06222(13) 0.0497(6) Uani . . 1.000
C C5B -0.36718(13) 0.53043(18) 0.02755(13) 0.0450(6) Uani . . 1.000
C C6B -0.27991(11) 0.61271(14) 0.06581(11) 0.0307(5) Uani . . 1.000
Cl Cl4 0.54291(3) 1.11882(5) 0.10952(4) 0.0515(2) Uani . . 1.000
Cl Cl5 0.54725(3) 0.83387(4) 0.18411(4) 0.0524(2) Uani . . 1.000
O O11 0.18070(8) 0.83778(9) 0.29506(7) 0.0299(3) Uani . . 1.000
O O12 0.11586(8) 0.85918(11) 0.14445(8) 0.0389(4) Uani . . 1.000
O O21 0.13624(7) 1.13683(10) 0.22891(7) 0.0297(3) Uani . . 1.000
O O22 0.15811(8) 1.22425(10) 0.09345(7) 0.0358(3) Uani . . 1.000
C C1 0.27323(10) 0.94353(13) 0.19485(9) 0.0210(4) Uani . . 1.000
C C2 0.27163(10) 1.06951(13) 0.16393(9) 0.0210(4) Uani . . 1.000
C C3 0.35526(11) 1.12116(14) 0.13754(10) 0.0268(4) Uani . . 1.000
C C4 0.44021(11) 1.05035(15) 0.14302(11) 0.0305(4) Uani . . 1.000
C C5 0.44221(11) 0.92640(15) 0.17569(11) 0.0301(4) Uani . . 1.000
C C6 0.35922(11) 0.87368(14) 0.20170(10) 0.0269(4) Uani . . 1.000
C C11 0.18131(10) 0.87618(13) 0.21301(10) 0.0232(4) Uani . . 1.000
C C21 0.18026(10) 1.15032(12) 0.16064(10) 0.0231(4) Uani . . 1.000
O O1W -0.03247(9) 0.70087(11) 0.06512(9) 0.0373(4) Uani . . 1.000
H H11A -0.0042(15) 0.6453(17) 0.2911(12) 0.044(5) Uiso . . 1.000
H H12A 0.0983(13) 0.6934(18) 0.2940(12) 0.047(5) Uiso . . 1.000
H H21A 0.04250 0.53200 0.42450 0.0410 Uiso calc R 1.000
H H22A 0.07470 0.67630 0.44360 0.0410 Uiso calc R 1.000
H H31A 0.20710 0.53740 0.49960 0.0470 Uiso calc R 1.000
H H32A 0.23520 0.62960 0.42130 0.0470 Uiso calc R 1.000
H H41A 0.28250 0.42150 0.39070 0.0430 Uiso calc R 1.000
H H42A 0.17310 0.37180 0.39020 0.0430 Uiso calc R 1.000
H H51A 0.19630 0.39930 0.23550 0.0410 Uiso calc R 1.000
H H52A 0.22980 0.54270 0.25650 0.0410 Uiso calc R 1.000
H H61A 0.06540 0.54200 0.18130 0.0400 Uiso calc R 1.000
H H62A 0.03600 0.44680 0.25720 0.0400 Uiso calc R 1.000
H H11B -0.1854(13) 0.4805(16) 0.1236(12) 0.039(5) Uiso . . 1.000
H H12B -0.1311(14) 0.5936(17) 0.0945(12) 0.044(5) Uiso . . 1.000
H H21B -0.11070 0.42400 0.00270 0.0400 Uiso calc R 1.000
H H22B -0.16390 0.53940 -0.05660 0.0400 Uiso calc R 1.000
H H31B -0.26200 0.32150 -0.00100 0.0510 Uiso calc R 1.000
H H32B -0.24730 0.35100 -0.10520 0.0510 Uiso calc R 1.000
H H41B -0.40870 0.40680 -0.08300 0.0600 Uiso calc R 1.000
H H42B -0.35120 0.52820 -0.11150 0.0600 Uiso calc R 1.000
H H51B -0.42700 0.58320 0.01540 0.0540 Uiso calc R 1.000
H H52B -0.37650 0.46610 0.07440 0.0540 Uiso calc R 1.000
H H61B -0.27540 0.68360 0.02260 0.0370 Uiso calc R 1.000
H H62B -0.28900 0.64860 0.12630 0.0370 Uiso calc R 1.000
H H3 0.35400 1.20570 0.11560 0.0320 Uiso calc R 1.000
H H6 0.36120 0.78950 0.22430 0.0320 Uiso calc R 1.000
H H11W 0.0098(15) 0.749(2) 0.0907(14) 0.058(6) Uiso . . 1.000
H H12W -0.0602(15) 0.733(2) 0.0152(15) 0.062(7) Uiso . . 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'
Cl Cl 0.1484 0.1585 '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
H11W O1W H12W . . . 109(2) no
C2A N1A C6A . . . 112.57(12) no
C6A N1A H11A . . . 107.3(11) no
H11A N1A H12A . . . 111.6(16) no
C2A N1A H12A . . . 107.2(11) no
C2A N1A H11A . . . 109.7(11) no
C6A N1A H12A . . . 108.6(11) no
C2B N1B C6B . . . 112.55(12) no
C2B N1B H11B . . . 109.9(11) no
H11B N1B H12B . . . 108.0(15) no
C6B N1B H11B . . . 111.6(12) no
C6B N1B H12B . . . 110.0(11) no
C2B N1B H12B . . . 104.5(11) no
N1A C2A C3A . . . 110.25(13) no
C2A C3A C4A . . . 110.88(13) no
C3A C4A C5A . . . 109.92(13) no
C4A C5A C6A . . . 110.74(13) no
N1A C6A C5A . . . 111.02(13) no
H21A C2A H22A . . . 108.00 no
N1A C2A H21A . . . 110.00 no
C3A C2A H21A . . . 110.00 no
C3A C2A H22A . . . 110.00 no
N1A C2A H22A . . . 110.00 no
C2A C3A H32A . . . 109.00 no
C2A C3A H31A . . . 109.00 no
C4A C3A H32A . . . 109.00 no
C4A C3A H31A . . . 109.00 no
H31A C3A H32A . . . 108.00 no
H41A C4A H42A . . . 108.00 no
C3A C4A H42A . . . 110.00 no
C5A C4A H41A . . . 110.00 no
C5A C4A H42A . . . 110.00 no
C3A C4A H41A . . . 110.00 no
C4A C5A H52A . . . 110.00 no
C6A C5A H52A . . . 110.00 no
H51A C5A H52A . . . 108.00 no
C4A C5A H51A . . . 110.00 no
C6A C5A H51A . . . 109.00 no
N1A C6A H62A . . . 109.00 no
N1A C6A H61A . . . 109.00 no
C5A C6A H62A . . . 109.00 no
C5A C6A H61A . . . 109.00 no
H61A C6A H62A . . . 108.00 no
N1B C2B C3B . . . 110.24(13) no
C2B C3B C4B . . . 110.89(14) no
C3B C4B C5B . . . 109.92(15) no
C4B C5B C6B . . . 111.52(15) no
N1B C6B C5B . . . 110.65(13) no
N1B C2B H22B . . . 110.00 no
C3B C2B H21B . . . 110.00 no
N1B C2B H21B . . . 110.00 no
H21B C2B H22B . . . 108.00 no
C3B C2B H22B . . . 110.00 no
C2B C3B H32B . . . 109.00 no
C4B C3B H31B . . . 109.00 no
C2B C3B H31B . . . 109.00 no
H31B C3B H32B . . . 108.00 no
C4B C3B H32B . . . 109.00 no
C3B C4B H41B . . . 110.00 no
C5B C4B H41B . . . 110.00 no
C5B C4B H42B . . . 110.00 no
H41B C4B H42B . . . 108.00 no
C3B C4B H42B . . . 110.00 no
C4B C5B H52B . . . 109.00 no
C6B C5B H51B . . . 109.00 no
C4B C5B H51B . . . 109.00 no
H51B C5B H52B . . . 108.00 no
C6B C5B H52B . . . 109.00 no
N1B C6B H62B . . . 110.00 no
C5B C6B H61B . . . 110.00 no
C5B C6B H62B . . . 110.00 no
H61B C6B H62B . . . 108.00 no
N1B C6B H61B . . . 110.00 no
C2 C1 C6 . . . 119.57(13) no
C2 C1 C11 . . . 122.20(12) no
C6 C1 C11 . . . 118.00(12) no
C1 C2 C21 . . . 120.70(12) no
C3 C2 C21 . . . 119.76(12) no
C1 C2 C3 . . . 119.53(13) no
C2 C3 C4 . . . 120.59(14) no
Cl4 C4 C3 . . . 119.00(12) no
Cl4 C4 C5 . . . 121.28(12) no
C3 C4 C5 . . . 119.71(14) no
Cl5 C5 C6 . . . 118.37(12) no
C4 C5 C6 . . . 120.23(14) no
Cl5 C5 C4 . . . 121.41(12) no
C1 C6 C5 . . . 120.34(14) no
O11 C11 C1 . . . 117.21(12) no
O12 C11 C1 . . . 116.31(12) no
O11 C11 O12 . . . 126.39(14) no
O21 C21 C2 . . . 115.02(12) no
O22 C21 C2 . . . 117.83(12) no
O21 C21 O22 . . . 127.12(13) no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 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
Cl4 C4 . . 1.7401(16) no
Cl5 C5 . . 1.7408(16) no
O11 C11 . . 1.2675(18) no
O12 C11 . . 1.2431(18) no
O21 C21 . . 1.2635(17) no
O22 C21 . . 1.2522(17) no
O1W H11W . . 0.82(2) no
O1W H12W . . 0.84(2) no
N1A C6A . . 1.491(2) no
N1A C2A . . 1.4960(19) no
N1A H11A . . 0.90(2) no
N1A H12A . . 0.914(19) no
N1B C6B . . 1.490(2) no
N1B C2B . . 1.495(2) no
N1B H12B . . 0.975(19) no
N1B H11B . . 0.896(17) no
C2A C3A . . 1.519(2) no
C3A C4A . . 1.528(2) no
C4A C5A . . 1.519(2) no
C5A C6A . . 1.523(2) no
C2A H22A . . 0.9900 no
C2A H21A . . 0.9900 no
C3A H31A . . 0.9900 no
C3A H32A . . 0.9900 no
C4A H41A . . 0.9900 no
C4A H42A . . 0.9900 no
C5A H51A . . 0.9900 no
C5A H52A . . 0.9900 no
C6A H62A . . 0.9900 no
C6A H61A . . 0.9900 no
C2B C3B . . 1.514(2) no
C3B C4B . . 1.522(3) no
C4B C5B . . 1.528(3) no
C5B C6B . . 1.517(2) no
C2B H21B . . 0.9900 no
C2B H22B . . 0.9900 no
C3B H31B . . 0.9900 no
C3B H32B . . 0.9900 no
C4B H41B . . 0.9900 no
C4B H42B . . 0.9900 no
C5B H52B . . 0.9900 no
C5B H51B . . 0.9900 no
C6B H62B . . 0.9900 no
C6B H61B . . 0.9900 no
C1 C11 . . 1.522(2) no
C1 C2 . . 1.4080(19) no
C1 C6 . . 1.391(2) no
C2 C21 . . 1.522(2) no
C2 C3 . . 1.394(2) no
C3 C4 . . 1.386(2) no
C4 C5 . . 1.396(2) no
C5 C6 . . 1.388(2) no
C3 H3 . . 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 O21 2_545 0.90(2) 1.80(2) 2.6820(17) 164.0(17) yes
N1A H12A O11 . 0.914(19) 1.907(19) 2.8085(17) 168.4(16) yes
N1B H11B O11 2_545 0.896(17) 1.917(17) 2.8054(16) 170.7(16) yes
N1B H12B O1W . 0.975(19) 1.882(19) 2.7866(18) 153.1(15) yes
O1W H11W O12 . 0.82(2) 1.93(2) 2.7490(17) 176(2) yes
O1W H12W O22 3_575 0.84(2) 1.96(2) 2.7639(17) 162(2) yes
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 . . . . 56.24(17) no
C2A N1A C6A C5A . . . . -55.92(17) no
C6B N1B C2B C3B . . . . -57.31(16) no
C2B N1B C6B C5B . . . . 56.01(17) no
N1A C2A C3A C4A . . . . -56.58(17) no
C2A C3A C4A C5A . . . . 57.19(18) no
C3A C4A C5A C6A . . . . -56.35(17) no
C4A C5A C6A N1A . . . . 55.68(17) no
N1B C2B C3B C4B . . . . 57.22(18) no
C2B C3B C4B C5B . . . . -56.38(19) no
C3B C4B C5B C6B . . . . 55.2(2) no
C4B C5B C6B N1B . . . . -54.75(18) no
C6 C1 C2 C3 . . . . 2.2(2) no
C6 C1 C2 C21 . . . . -176.73(13) no
C11 C1 C2 C3 . . . . -172.11(13) no
C11 C1 C2 C21 . . . . 8.95(19) no
C2 C1 C6 C5 . . . . -1.9(2) no
C11 C1 C6 C5 . . . . 172.68(13) no
C2 C1 C11 O11 . . . . -118.74(15) no
C2 C1 C11 O12 . . . . 64.50(18) no
C6 C1 C11 O11 . . . . 66.86(17) no
C6 C1 C11 O12 . . . . -109.90(15) no
C1 C2 C3 C4 . . . . -1.1(2) no
C21 C2 C3 C4 . . . . 177.83(13) no
C1 C2 C21 O21 . . . . 40.40(18) no
C1 C2 C21 O22 . . . . -141.41(13) no
C3 C2 C21 O21 . . . . -138.54(13) no
C3 C2 C21 O22 . . . . 39.65(19) no
C2 C3 C4 Cl4 . . . . -179.89(11) no
C2 C3 C4 C5 . . . . -0.3(2) no
Cl4 C4 C5 Cl5 . . . . -0.3(2) no
Cl4 C4 C5 C6 . . . . -179.77(12) no
C3 C4 C5 Cl5 . . . . -179.84(12) no
C3 C4 C5 C6 . . . . 0.7(2) no
Cl5 C5 C6 C1 . . . . -179.07(11) no
C4 C5 C6 C1 . . . . 0.4(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654249
