#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/77/2017710.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_2017710
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          'C4 H12 N +, C8 H3 Cl2 O4 -'
_chemical_formula_moiety         'C4 H12 N +, C8 H3 Cl2 O4 -'
_chemical_formula_sum            'C12 H15 Cl2 N O4'
_chemical_formula_weight         308.14
_chemical_melting_point          443
_chemical_name_common
'diethylaminium hydrogen 4,5-dichlorophthalate'
_chemical_name_systematic
;
diethylaminium 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                 104.580(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9588(13)
_cell_length_b                   9.9042(11)
_cell_length_c                   17.062(3)
_cell_measurement_reflns_used    2315
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      32.40
_cell_measurement_theta_min      2.90
_cell_volume                     1465.2(4)
_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_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5638
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.451
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0641P)²+0.1213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1062
_reflns_number_gt                2159
_reflns_number_total             2802
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3347.cif
_cod_data_source_block           II
_cod_original_cell_volume        1465.2(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017710
_cod_database_fobs_code          2017710
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
Cl Cl4 0.43514(6) -0.20944(6) 0.30016(3) 0.0438(2) Uani . . 1.000
Cl Cl5 0.45031(7) -0.32604(6) 0.47681(4) 0.0495(2) Uani . . 1.000
O O11 0.82585(18) -0.02229(15) 0.66675(8) 0.0437(5) Uani . . 1.000
O O12 0.9418(2) 0.12902(18) 0.60850(10) 0.0531(6) Uani . . 1.000
O O21 0.92748(19) 0.21909(18) 0.47700(9) 0.0508(6) Uani . . 1.000
O O22 0.7828(2) 0.20048(17) 0.35291(9) 0.0552(6) Uani . . 1.000
C C1 0.7437(2) -0.01323(18) 0.52381(11) 0.0274(5) Uani . . 1.000
C C2 0.7347(2) 0.04067(19) 0.44596(11) 0.0280(6) Uani . . 1.000
C C3 0.6346(2) -0.0214(2) 0.37922(11) 0.0313(6) Uani . . 1.000
C C4 0.5489(2) -0.1348(2) 0.38645(11) 0.0308(6) Uani . . 1.000
C C5 0.5570(2) -0.18594(19) 0.46316(12) 0.0310(6) Uani . . 1.000
C C6 0.6516(2) -0.12484(19) 0.52986(11) 0.0290(6) Uani . . 1.000
C C11 0.8434(2) 0.0344(2) 0.60563(11) 0.0330(6) Uani . . 1.000
C C21 0.8196(2) 0.1619(2) 0.42353(12) 0.0362(7) Uani . . 1.000
N N1A 0.9508(2) 0.41802(18) 0.32003(10) 0.0332(5) Uani . . 1.000
C C1A 1.1027(3) 0.3524(3) 0.32661(17) 0.0586(9) Uani . . 1.000
C C1B 0.9510(3) 0.5322(2) 0.37563(14) 0.0499(8) Uani . . 1.000
C C2A 1.2148(3) 0.4385(4) 0.30110(18) 0.0765(13) Uani . . 1.000
C C2B 0.7912(4) 0.5749(4) 0.3736(2) 0.0921(14) Uani . . 1.000
H H3 0.62520 0.01590 0.32690 0.0380 Uiso calc R 1.000
H H6 0.65440 -0.15980 0.58210 0.0350 Uiso calc R 1.000
H H12 0.936(4) 0.167(3) 0.554(2) 0.086 Uiso . . 1.000
H H1A 0.914(2) 0.442(2) 0.2684(14) 0.038(6) Uiso . . 1.000
H H2A 0.888(3) 0.349(3) 0.3314(16) 0.060(8) Uiso . . 1.000
H H11A 1.14620 0.32490 0.38360 0.0700 Uiso calc R 1.000
H H11B 1.00780 0.60910 0.35990 0.0600 Uiso calc R 1.000
H H12A 1.08660 0.26960 0.29310 0.0700 Uiso calc R 1.000
H H12B 1.00490 0.50510 0.43140 0.0600 Uiso calc R 1.000
H H21A 1.23180 0.52080 0.33400 0.0920 Uiso calc R 1.000
H H21B 0.71830 0.50620 0.34570 0.1110 Uiso calc R 1.000
H H22A 1.17520 0.46240 0.24390 0.0920 Uiso calc R 1.000
H H22B 0.76880 0.66100 0.34480 0.1110 Uiso calc R 1.000
H H23A 1.31250 0.38970 0.30840 0.0920 Uiso calc R 1.000
H H23B 0.78090 0.58570 0.42910 0.1110 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 . . . 111.7(19) no
C1A N1A C1B . . . 115.69(19) no
C1B N1A H1A . . . 111.8(13) no
C1B N1A H2A . . . 109.3(17) no
H1A N1A H2A . . . 108(2) no
C1A N1A H1A . . . 107.2(13) no
C1A N1A H2A . . . 104.6(18) no
C6 C1 C11 . . . 113.33(16) no
C2 C1 C6 . . . 118.18(17) no
C2 C1 C11 . . . 128.49(16) no
C1 C2 C21 . . . 128.33(17) no
C1 C2 C3 . . . 118.09(17) no
C3 C2 C21 . . . 113.58(16) no
C2 C3 C4 . . . 122.65(17) no
Cl4 C4 C5 . . . 121.73(15) no
C3 C4 C5 . . . 118.81(17) no
Cl4 C4 C3 . . . 119.47(14) no
Cl5 C5 C4 . . . 121.26(15) no
Cl5 C5 C6 . . . 119.11(15) no
C4 C5 C6 . . . 119.63(17) no
C1 C6 C5 . . . 122.58(17) no
O11 C11 O12 . . . 122.44(18) no
O11 C11 C1 . . . 117.61(17) no
O12 C11 C1 . . . 119.95(17) no
O21 C21 O22 . . . 121.95(19) no
O22 C21 C2 . . . 117.71(18) no
O21 C21 C2 . . . 120.33(17) 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
N1A C1A C2A . . . 114.0(2) no
N1A C1B C2B . . . 111.0(2) no
N1A C1A H11A . . . 109.00 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 C1B H11B . . . 109.00 no
N1A C1B H12B . . . 109.00 no
C2B C1B H11B . . . 109.00 no
C2B C1B H12B . . . 110.00 no
H11B C1B H12B . . . 108.00 no
C1A C2A H21A . . . 109.00 no
C1A C2A H22A . . . 109.00 no
C1A C2A H23A . . . 109.00 no
H21A C2A H22A . . . 110.00 no
H21A C2A H23A . . . 109.00 no
H22A C2A H23A . . . 109.00 no
C1B C2B H21B . . . 110.00 no
C1B C2B H22B . . . 110.00 no
C1B C2B H23B . . . 109.00 no
H21B C2B H22B . . . 109.00 no
H21B C2B H23B . . . 109.00 no
H22B C2B H23B . . . 109.00 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 . . 1.731(2) no
Cl5 C5 . . 1.734(2) no
O11 C11 . . 1.229(2) no
O12 C11 . . 1.279(3) no
O21 C21 . . 1.282(3) no
O22 C21 . . 1.227(2) no
O12 H12 . . 0.99(3) no
N1A C1B . . 1.476(3) no
N1A C1A . . 1.487(3) no
N1A H2A . . 0.94(3) no
N1A H1A . . 0.89(2) no
C1 C6 . . 1.399(3) no
C1 C2 . . 1.415(3) no
C1 C11 . . 1.530(3) no
C2 C21 . . 1.521(3) no
C2 C3 . . 1.402(3) no
C3 C4 . . 1.383(3) no
C4 C5 . . 1.388(3) no
C5 C6 . . 1.376(3) no
C3 H3 . . 0.9500 no
C6 H6 . . 0.9500 no
C1A C2A . . 1.465(4) no
C1B C2B . . 1.485(5) no
C1A H11A . . 0.9900 no
C1A H12A . . 0.9900 no
C1B H11B . . 0.9900 no
C1B H12B . . 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
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 O11 4_554 0.89(2) 1.89(2) 2.772(2) 169.6(19) yes
N1A H2A O22 . 0.94(3) 1.83(3) 2.765(3) 173(3) yes
O12 H12 O21 . 0.99(3) 1.40(3) 2.388(2) 179(4) yes
C3 H3 O22 . 0.95 2.28 2.663(3) 103 no
C6 H6 O11 . 0.95 2.28 2.662(2) 103 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
C1A N1A C1B C2B . . . . -170.6(2) no
C1B N1A C1A C2A . . . . -67.1(3) no
C6 C1 C2 C21 . . . . 178.71(18) no
C6 C1 C2 C3 . . . . -0.4(3) no
C2 C1 C6 C5 . . . . 2.0(3) no
C11 C1 C6 C5 . . . . -177.95(17) no
C2 C1 C11 O11 . . . . 175.50(19) no
C2 C1 C11 O12 . . . . -5.3(3) no
C6 C1 C11 O11 . . . . -4.6(3) no
C11 C1 C2 C3 . . . . 179.57(18) no
C11 C1 C2 C21 . . . . -1.3(3) no
C6 C1 C11 O12 . . . . 174.69(18) no
C1 C2 C21 O21 . . . . 8.8(3) no
C1 C2 C21 O22 . . . . -172.41(19) no
C21 C2 C3 C4 . . . . 178.72(17) no
C3 C2 C21 O22 . . . . 6.7(3) no
C3 C2 C21 O21 . . . . -172.07(18) no
C1 C2 C3 C4 . . . . -2.1(3) no
C2 C3 C4 Cl4 . . . . -176.95(15) no
C2 C3 C4 C5 . . . . 2.9(3) no
Cl4 C4 C5 C6 . . . . 178.62(15) no
C3 C4 C5 Cl5 . . . . 178.93(15) no
Cl4 C4 C5 Cl5 . . . . -1.2(2) no
C3 C4 C5 C6 . . . . -1.2(3) no
C4 C5 C6 C1 . . . . -1.2(3) no
Cl5 C5 C6 C1 . . . . 178.64(15) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26231168
