#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/04/2210434.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_2210434
loop_
_publ_author_name
'Cai, Min-Ying'
'Chen, Jian-Zhong'
_publ_section_title
;
 4-Dimethylaminopyridinium dichloroacetate dichloroacetic acid
;
_journal_coeditor_code           XU2088
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3996
_journal_page_last               o3997
_journal_paper_doi               10.1107/S1600536806032363
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C7 H11 N2 +, C2 H Cl2 O2 -, C2 H2 Cl2 O2'
_chemical_formula_moiety         'C7 H11 N2 +, C2 H Cl2 O2 -, C2 H2 Cl2 O2'
_chemical_formula_sum            'C11 H14 Cl4 N2 O4'
_chemical_formula_weight         380.04
_chemical_name_systematic
;
4-Dimethylaminopyridinium dichloroacetate dichloroacetic acid
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 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                 111.37(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.8300(18)
_cell_length_b                   5.8740(12)
_cell_length_c                   17.096(3)
_cell_measurement_reflns_used    3634
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.4
_cell_volume                     825.8(3)
_computing_cell_refinement       TEXRAY
_computing_data_collection
'TEXRAY (Molecular Structure Corporation, 1999)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1999)'
_computing_molecular_graphics    'ORTEX (McArdle, 1995)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Rigaku Weissenberg IP'
_diffrn_measurement_method       ω
_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  0.055
_diffrn_reflns_av_sigmaI/netI    0.087
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7654
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.4
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.27
_refine_ls_abs_structure_details 'Flack (1983), 1730 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.41(9)
_refine_ls_extinction_coef       0.055(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3634
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.066
_refine_ls_R_factor_gt           0.049
_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)+(0.0806P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.136
_refine_ls_wR_factor_ref         0.146
_reflns_number_gt                2604
_reflns_number_total             3634
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2088.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               2210434
_cod_database_fobs_code          2210434
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, 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
Cl Cl1 0.94699(16) 0.71566(17) 0.32488(10) 0.0812(4) Uani d . 1
Cl Cl2 1.06169(13) 0.3092(2) 0.42635(7) 0.0724(4) Uani d . 1
Cl Cl3 0.18669(16) -0.22003(18) 0.16499(11) 0.0839(5) Uani d . 1
Cl Cl4 0.10189(14) 0.2065(2) 0.07354(7) 0.0774(4) Uani d . 1
N N1 0.6837(5) 0.1679(6) 0.6095(2) 0.0621(9) Uani d . 1
H H 0.539(7) 0.210(9) 0.238(3) 0.070(15) Uiso d . 1
N N2 0.5194(5) 0.7138(5) 0.4492(2) 0.0511(7) Uani d . 1
O O1 0.7144(3) 0.3106(6) 0.29367(18) 0.0637(8) Uani d . 1
O O2 0.8394(4) 0.1883(5) 0.2092(2) 0.0584(8) Uani d . 1
O O3 0.3383(4) 0.2870(6) 0.28991(19) 0.0640(8) Uani d . 1
O O4 0.4521(4) 0.1405(6) 0.20425(19) 0.0566(7) Uani d . 1
H H1 0.723(6) 0.054(9) 0.649(3) 0.068(13) Uiso d . 1
C C1 0.5706(4) 0.5337(6) 0.5011(2) 0.0439(7) Uani d . 1
C C2 0.5085(5) 0.4829(6) 0.5641(2) 0.0508(8) Uani d . 1
H H2 0.4264 0.5724 0.5700 0.061 Uiso calc R 1
C C3 0.5675(6) 0.3054(8) 0.6158(3) 0.0615(11) Uani d . 1
H H3 0.5261 0.2768 0.6576 0.074 Uiso calc R 1
C C4 0.7429(6) 0.2066(7) 0.5486(3) 0.0597(10) Uani d . 1
H H4 0.8223 0.1098 0.5437 0.072 Uiso calc R 1
C C5 0.6898(5) 0.3842(7) 0.4939(3) 0.0564(9) Uani d . 1
H H5 0.7320 0.4065 0.4519 0.068 Uiso calc R 1
C C6 0.3867(6) 0.8564(7) 0.4525(4) 0.0688(12) Uani d . 1
H H6A 0.3664 0.9764 0.4118 0.103 Uiso calc R 1
H H6B 0.4159 0.9211 0.5077 0.103 Uiso calc R 1
H H6C 0.2903 0.7657 0.4403 0.103 Uiso calc R 1
C C7 0.5864(8) 0.7627(9) 0.3853(3) 0.0733(14) Uani d . 1
H H7A 0.5357 0.8967 0.3549 0.110 Uiso calc R 1
H H7B 0.5665 0.6362 0.3473 0.110 Uiso calc R 1
H H7C 0.7014 0.7874 0.4114 0.110 Uiso calc R 1
C C8 0.9875(4) 0.4221(7) 0.3233(2) 0.0496(9) Uani d . 1
H H8 1.0704 0.4005 0.2984 0.060 Uiso calc R 1
C C9 0.8312(4) 0.2938(6) 0.2692(2) 0.0425(8) Uani d . 1
C C10 0.1705(5) 0.0782(6) 0.1735(2) 0.0453(7) Uani d . 1
H H10 0.0905 0.1089 0.1996 0.054 Uiso calc R 1
C C11 0.3317(5) 0.1801(6) 0.2286(2) 0.0424(8) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0625(7) 0.0498(5) 0.1175(11) -0.0094(5) 0.0162(7) -0.0052(7)
Cl2 0.0595(7) 0.0821(8) 0.0559(6) 0.0061(6) -0.0024(5) 0.0006(6)
Cl3 0.0582(7) 0.0481(5) 0.1368(12) -0.0102(5) 0.0253(8) 0.0027(7)
Cl4 0.0574(7) 0.0934(9) 0.0655(7) -0.0161(6) 0.0034(5) 0.0191(6)
N1 0.057(2) 0.067(2) 0.0494(17) 0.0096(17) 0.0035(16) 0.0189(17)
N2 0.0519(19) 0.0477(15) 0.0538(16) 0.0084(14) 0.0193(14) 0.0082(14)
O1 0.0402(16) 0.100(2) 0.0568(16) -0.0207(15) 0.0252(13) -0.0316(15)
O2 0.0496(17) 0.0645(16) 0.0664(18) -0.0119(13) 0.0273(14) -0.0287(14)
O3 0.0521(18) 0.084(2) 0.0592(17) -0.0013(15) 0.0236(15) -0.0199(15)
O4 0.0347(13) 0.0766(17) 0.0615(16) -0.0129(13) 0.0212(13) -0.0167(14)
C1 0.0379(16) 0.0483(16) 0.0408(15) -0.0027(14) 0.0088(13) -0.0037(14)
C2 0.048(2) 0.0548(18) 0.0544(19) 0.0001(16) 0.0244(17) -0.0035(16)
C3 0.066(3) 0.072(3) 0.049(2) -0.006(2) 0.022(2) 0.0008(19)
C4 0.046(2) 0.062(2) 0.062(2) 0.0159(18) 0.0087(19) 0.006(2)
C5 0.048(2) 0.071(2) 0.0538(19) 0.0153(18) 0.0224(17) 0.0105(19)
C6 0.053(2) 0.051(2) 0.101(3) 0.0129(19) 0.026(2) 0.011(2)
C7 0.099(4) 0.063(2) 0.066(3) 0.003(3) 0.039(3) 0.005(2)
C8 0.0326(18) 0.061(2) 0.055(2) -0.0051(15) 0.0151(16) -0.0145(18)
C9 0.0323(18) 0.0492(19) 0.045(2) -0.0002(14) 0.0130(15) -0.0018(15)
C10 0.0379(17) 0.0487(17) 0.0535(18) -0.0037(14) 0.0216(15) -0.0008(16)
C11 0.044(2) 0.0409(17) 0.045(2) -0.0018(14) 0.0183(16) 0.0040(15)
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
_geom_angle_publ_flag
C3 N1 C4 119.0(4) ?
C3 N1 H1 118(3) no
C4 N1 H1 123(3) no
C1 N2 C7 121.4(4) no
C1 N2 C6 120.4(4) no
C7 N2 C6 118.1(4) no
C11 O4 H 110(4) no
N2 C1 C2 122.6(3) no
N2 C1 C5 120.8(3) no
C2 C1 C5 116.6(3) no
C3 C2 C1 120.1(4) no
C3 C2 H2 120.0 no
C1 C2 H2 120.0 no
N1 C3 C2 122.7(4) no
N1 C3 H3 118.6 no
C2 C3 H3 118.6 no
N1 C4 C5 121.8(4) no
N1 C4 H4 119.1 no
C5 C4 H4 119.1 no
C4 C5 C1 119.7(4) no
C4 C5 H5 120.1 no
C1 C5 H5 120.1 no
N2 C6 H6A 109.5 no
N2 C6 H6B 109.5 no
H6A C6 H6B 109.5 no
N2 C6 H6C 109.5 no
H6A C6 H6C 109.5 no
H6B C6 H6C 109.5 no
N2 C7 H7A 109.5 no
N2 C7 H7B 109.5 no
H7A C7 H7B 109.5 no
N2 C7 H7C 109.5 no
H7A C7 H7C 109.5 no
H7B C7 H7C 109.5 no
C9 C8 Cl1 110.1(3) no
C9 C8 Cl2 109.8(3) no
Cl1 C8 Cl2 110.8(2) no
C9 C8 H8 108.7 no
Cl1 C8 H8 108.7 no
Cl2 C8 H8 108.7 no
O2 C9 O1 129.0(3) no
O2 C9 C8 115.8(3) no
O1 C9 C8 115.2(3) no
C11 C10 Cl4 110.3(2) no
C11 C10 Cl3 110.9(3) no
Cl4 C10 Cl3 110.7(2) no
C11 C10 H10 108.3 no
Cl4 C10 H10 108.3 no
Cl3 C10 H10 108.3 no
O3 C11 O4 126.0(4) no
O3 C11 C10 118.9(4) no
O4 C11 C10 115.1(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C8 1.764(4) no
Cl2 C8 1.769(4) no
Cl3 C10 1.768(4) no
Cl4 C10 1.761(4) no
N1 C3 1.340(6) no
N1 C4 1.344(6) no
N1 H1 0.93(5) ?
N2 C1 1.349(5) ?
N2 C7 1.448(6) no
N2 C6 1.459(5) no
O1 C9 1.250(5) yes
O2 C9 1.222(5) yes
O3 C11 1.205(5) yes
O4 C11 1.296(5) yes
O4 H 0.88(5) ?
C1 C2 1.408(5) no
C1 C5 1.410(5) no
C2 C3 1.343(6) no
C2 H2 0.9300 no
C3 H3 0.9300 no
C4 C5 1.366(6) no
C4 H4 0.9300 no
C5 H5 0.9300 no
C6 H6A 0.9600 no
C6 H6B 0.9600 no
C6 H6C 0.9600 no
C7 H7A 0.9600 no
C7 H7B 0.9600 no
C7 H7C 0.9600 no
C8 C9 1.549(5) no
C8 H8 0.9800 no
C10 C11 1.515(5) no
C10 H10 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
O4 H O1 . 0.88(5) 1.60(6) 2.474(3) 171(6)
N1 H1 O2 2 0.93(5) 1.84(5) 2.732(4) 162(4)
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
_geom_torsion_publ_flag
C7 N2 C1 C2 179.6(4) no
C6 N2 C1 C2 -4.5(6) no
C7 N2 C1 C5 -1.1(6) no
C6 N2 C1 C5 174.9(4) no
N2 C1 C2 C3 -177.9(4) no
C5 C1 C2 C3 2.7(5) no
C4 N1 C3 C2 -0.7(7) no
C1 C2 C3 N1 -1.2(6) no
C3 N1 C4 C5 1.0(7) no
N1 C4 C5 C1 0.6(7) no
N2 C1 C5 C4 178.2(4) no
C2 C1 C5 C4 -2.4(6) no
Cl1 C8 C9 O2 120.8(3) no
Cl2 C8 C9 O2 -117.0(3) no
Cl1 C8 C9 O1 -60.0(4) no
Cl2 C8 C9 O1 62.2(4) no
Cl4 C10 C11 O3 114.7(3) no
Cl3 C10 C11 O3 -122.2(3) no
Cl4 C10 C11 O4 -65.7(4) no
Cl3 C10 C11 O4 57.4(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127381
