#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/77/2017709.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_2017709
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          'C6 H16 N +, C8 H3 Cl2 O4 -'
_chemical_formula_moiety         'C6 H16 N +, C8 H3 Cl2 O4 -'
_chemical_formula_sum            'C14 H19 Cl2 N O4'
_chemical_formula_weight         336.20
_chemical_melting_point          353
_chemical_name_common
'triethylaminium hydrogen 4,5-dichlorophthalate'
_chemical_name_systematic
;
triethylaminium 2-carboxy-4,5-dichlorobenzoate
;
_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                 98.576(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3206(7)
_cell_length_b                   11.2201(7)
_cell_length_c                   19.4813(12)
_cell_measurement_reflns_used    5117
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.80
_cell_measurement_theta_min      3.16
_cell_volume                     1582.3(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10740
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.26
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.237
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0293
_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)+(0.0454P)²+0.1656P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0771
_reflns_number_gt                2638
_reflns_number_total             3098
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3347.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017709
_cod_database_fobs_code          2017709
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 -0.05058(17) 0.95062(10) 0.36011(6) 0.0229(3) Uani . . 1.000
C C1A -0.2461(2) 0.91354(14) 0.36217(7) 0.0304(4) Uani . . 1.000
C C1B -0.0117(2) 1.07979(12) 0.37870(7) 0.0258(4) Uani . . 1.000
C C1C 0.0049(2) 0.91522(13) 0.29175(7) 0.0298(4) Uani . . 1.000
C C2A -0.3021(2) 0.92226(15) 0.43354(8) 0.0374(5) Uani . . 1.000
C C2B -0.1025(2) 1.16623(13) 0.32431(8) 0.0380(5) Uani . . 1.000
C C2C 0.2047(3) 0.94008(18) 0.28776(10) 0.0481(6) Uani . . 1.000
Cl Cl4 0.57140(5) 0.69357(4) 0.68165(2) 0.03460(10) Uani . . 1.000
Cl Cl5 0.53419(6) 0.40824(4) 0.68041(2) 0.03820(10) Uani . . 1.000
O O11 0.15312(15) 0.31238(9) 0.44967(5) 0.0364(4) Uani . . 1.000
O O12 0.05781(15) 0.46504(9) 0.38294(5) 0.0328(3) Uani . . 1.000
O O21 0.05047(15) 0.68027(9) 0.39185(5) 0.0349(3) Uani . . 1.000
O O22 0.18100(15) 0.82561(9) 0.45818(5) 0.0353(3) Uani . . 1.000
C C1 0.24055(17) 0.50253(13) 0.49736(6) 0.0205(4) Uani . . 1.000
C C2 0.25130(17) 0.62848(12) 0.49892(6) 0.0209(4) Uani . . 1.000
C C3 0.35682(17) 0.68325(13) 0.55642(6) 0.0231(4) Uani . . 1.000
C C4 0.44516(18) 0.61823(13) 0.61229(7) 0.0238(4) Uani . . 1.000
C C5 0.42972(18) 0.49501(13) 0.61168(7) 0.0242(4) Uani . . 1.000
C C6 0.33008(18) 0.43895(12) 0.55450(7) 0.0235(4) Uani . . 1.000
C C11 0.14444(19) 0.41945(13) 0.44043(7) 0.0252(4) Uani . . 1.000
C C21 0.15512(18) 0.71762(13) 0.44567(7) 0.0248(4) Uani . . 1.000
H H1A 0.019(2) 0.9082(14) 0.3943(8) 0.0300 Uiso . . 1.000
H H12 0.057(3) 0.553(2) 0.3840(11) 0.0590 Uiso . . 1.000
H H11A -0.26240 0.83020 0.34570 0.0370 Uiso calc R 1.000
H H11B 0.12350 1.09290 0.38540 0.0310 Uiso calc R 1.000
H H11C -0.07280 0.95900 0.25400 0.0360 Uiso calc R 1.000
H H12A -0.32940 0.96440 0.32980 0.0370 Uiso calc R 1.000
H H12B -0.05570 1.09700 0.42330 0.0310 Uiso calc R 1.000
H H12C -0.01900 0.82900 0.28420 0.0360 Uiso calc R 1.000
H H21A -0.42860 0.89250 0.43190 0.0450 Uiso calc R 1.000
H H21B -0.07430 1.24810 0.33990 0.0460 Uiso calc R 1.000
H H21C 0.23690 0.90650 0.24470 0.0580 Uiso calc R 1.000
H H22A -0.29630 1.00560 0.44870 0.0450 Uiso calc R 1.000
H H22B -0.23660 1.15410 0.31740 0.0460 Uiso calc R 1.000
H H22C 0.28200 0.90360 0.32760 0.0580 Uiso calc R 1.000
H H23A -0.21790 0.87430 0.46630 0.0450 Uiso calc R 1.000
H H23B -0.05540 1.15240 0.28050 0.0460 Uiso calc R 1.000
H H23C 0.22540 1.02640 0.28840 0.0580 Uiso calc R 1.000
H H3 0.36810 0.76760 0.55710 0.0280 Uiso calc R 1.000
H H6 0.32240 0.35440 0.55410 0.0280 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'
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
C11 O12 H12 . . . 112.2(12) no
C1A N1A C1C . . . 109.65(11) no
C1B N1A C1C . . . 113.58(11) no
C1A N1A C1B . . . 114.02(11) no
C1B N1A H1A . . . 105.2(10) no
C1C N1A H1A . . . 108.3(10) no
C1A N1A H1A . . . 105.6(9) no
N1A C1A C2A . . . 113.49(12) no
N1A C1B C2B . . . 113.53(11) no
N1A C1C C2C . . . 113.00(13) no
N1A C1A H12A . . . 109.00 no
C2A C1A H11A . . . 109.00 no
C2A C1A H12A . . . 109.00 no
H11A C1A H12A . . . 108.00 no
N1A C1A H11A . . . 109.00 no
N1A C1B H11B . . . 109.00 no
N1A C1B H12B . . . 109.00 no
C2B C1B H12B . . . 109.00 no
H11B C1B H12B . . . 108.00 no
C2B C1B H11B . . . 109.00 no
N1A C1C H11C . . . 109.00 no
N1A C1C H12C . . . 109.00 no
C2C C1C H12C . . . 109.00 no
H11C C1C H12C . . . 108.00 no
C2C C1C H11C . . . 109.00 no
C1A C2A H22A . . . 110.00 no
C1A C2A H23A . . . 109.00 no
H21A C2A H22A . . . 109.00 no
H21A C2A H23A . . . 109.00 no
H22A C2A H23A . . . 109.00 no
C1A C2A H21A . . . 109.00 no
C1B C2B H21B . . . 109.00 no
C1B C2B H23B . . . 109.00 no
H21B C2B H22B . . . 109.00 no
H21B C2B H23B . . . 109.00 no
H22B C2B H23B . . . 110.00 no
C1B C2B H22B . . . 109.00 no
C1C C2C H21C . . . 109.00 no
C1C C2C H23C . . . 109.00 no
H21C C2C H22C . . . 109.00 no
C1C C2C H22C . . . 109.00 no
H22C C2C H23C . . . 109.00 no
H21C C2C H23C . . . 110.00 no
C2 C1 C6 . . . 118.28(11) no
C2 C1 C11 . . . 129.73(11) no
C6 C1 C11 . . . 111.99(12) no
C1 C2 C3 . . . 118.45(11) no
C1 C2 C21 . . . 128.16(11) no
C3 C2 C21 . . . 113.36(12) no
C2 C3 C4 . . . 122.17(13) no
Cl4 C4 C5 . . . 121.64(11) no
C3 C4 C5 . . . 119.31(13) no
Cl4 C4 C3 . . . 119.05(11) no
Cl5 C5 C6 . . . 118.86(11) no
C4 C5 C6 . . . 119.41(13) no
Cl5 C5 C4 . . . 121.73(11) no
C1 C6 C5 . . . 122.34(13) no
O11 C11 C1 . . . 118.99(12) no
O12 C11 C1 . . . 119.52(12) no
O11 C11 O12 . . . 121.48(13) no
O21 C21 C2 . . . 120.07(12) no
O22 C21 C2 . . . 117.45(12) no
O21 C21 O22 . . . 122.46(13) no
C2 C3 H3 . . . 119.00 no
C4 C3 H3 . . . 119.00 no
C1 C6 H6 . . . 119.00 no
C5 C6 H6 . . . 119.00 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 . . 1.7383(14) no
Cl5 C5 . . 1.7378(14) no
O11 C11 . . 1.2150(18) no
O12 C11 . . 1.3063(17) no
O21 C21 . . 1.2737(17) no
O22 C21 . . 1.2448(18) no
O12 H12 . . 0.99(2) no
N1A C1A . . 1.4968(19) no
N1A C1B . . 1.5106(18) no
N1A C1C . . 1.5025(18) no
N1A H1A . . 0.910(15) no
C1A C2A . . 1.510(2) no
C1B C2B . . 1.515(2) no
C1C C2C . . 1.502(3) no
C1A H12A . . 0.9900 no
C1A H11A . . 0.9900 no
C1B H11B . . 0.9900 no
C1B H12B . . 0.9900 no
C1C H12C . . 0.9900 no
C1C H11C . . 0.9900 no
C2A H21A . . 0.9800 no
C2A H22A . . 0.9800 no
C2A H23A . . 0.9800 no
C2B H21B . . 0.9800 no
C2B H22B . . 0.9800 no
C2B H23B . . 0.9800 no
C2C H21C . . 0.9800 no
C2C H22C . . 0.9800 no
C2C H23C . . 0.9800 no
C1 C2 . . 1.415(2) no
C1 C11 . . 1.5366(19) no
C1 C6 . . 1.4000(18) no
C2 C3 . . 1.4040(17) no
C2 C21 . . 1.5344(19) no
C3 C4 . . 1.3875(19) no
C4 C5 . . 1.387(2) no
C5 C6 . . 1.3879(19) 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 H1A O21 . 0.910(15) 2.569(16) 3.1614(15) 123.3(12) yes
N1A H1A O22 . 0.910(15) 1.837(15) 2.7433(16) 173.7(14) yes
O12 H12 O21 . 0.99(2) 1.44(2) 2.4223(14) 175(2) yes
C3 H3 O22 . 0.95 2.29 2.6714(16) 103 no
C6 H6 O11 . 0.95 2.27 2.6602(17) 104 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
C1B N1A C1A C2A . . . . -63.19(16) no
C1C N1A C1A C2A . . . . 168.20(12) no
C1A N1A C1B C2B . . . . -69.93(15) no
C1C N1A C1B C2B . . . . 56.65(16) no
C1A N1A C1C C2C . . . . -175.17(13) no
C1B N1A C1C C2C . . . . 55.98(16) no
C6 C1 C2 C3 . . . . 2.37(18) no
C6 C1 C2 C21 . . . . -175.38(12) no
C11 C1 C2 C3 . . . . -176.80(12) no
C11 C1 C2 C21 . . . . 5.5(2) no
C2 C1 C6 C5 . . . . -0.73(19) no
C11 C1 C6 C5 . . . . 178.57(12) no
C2 C1 C11 O11 . . . . 179.64(13) no
C2 C1 C11 O12 . . . . 0.7(2) no
C6 C1 C11 O11 . . . . 0.44(18) no
C6 C1 C11 O12 . . . . -178.56(12) no
C1 C2 C3 C4 . . . . -2.12(19) no
C21 C2 C3 C4 . . . . 175.95(12) no
C1 C2 C21 O21 . . . . -0.1(2) no
C1 C2 C21 O22 . . . . 178.46(13) no
C3 C2 C21 O21 . . . . -177.98(12) no
C3 C2 C21 O22 . . . . 0.62(17) no
C2 C3 C4 Cl4 . . . . -179.47(10) no
C2 C3 C4 C5 . . . . 0.12(19) no
Cl4 C4 C5 Cl5 . . . . 0.45(17) no
Cl4 C4 C5 C6 . . . . -178.84(10) no
C3 C4 C5 Cl5 . . . . -179.14(10) no
C3 C4 C5 C6 . . . . 1.6(2) no
Cl5 C5 C6 C1 . . . . 179.42(10) no
C4 C5 C6 C1 . . . . -1.3(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26231167
