#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/39/2223944.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_2223944
loop_
_publ_author_name
'Ton, Cuong Quoc'
'Bolte, Michael'
_publ_section_title
;
 Bis(2,6-dicarboxypyridinium) dichloride acetone monosolvate
;
_journal_coeditor_code           NG2671
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2848
_journal_paper_doi               10.1107/S1600536809043220
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '2C7 H6 N O4 +, 2Cl -, C3 H6 O'
_chemical_formula_moiety         '2(C7 H6 N O4 +), 2(Cl -), C3 H6 O'
_chemical_formula_sum            'C17 H18 Cl2 N2 O9'
_chemical_formula_weight         465.23
_chemical_name_systematic
;
Bis(2,6-dicarboxypyridinium) dichloride acetone monosolvate
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.28(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.108(4)
_cell_length_b                   6.7877(14)
_cell_length_c                   15.224(3)
_cell_measurement_reflns_used    4736
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.9
_cell_measurement_theta_min      3.6
_cell_volume                     2046.0(8)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Stoe IPDSII two-circle'
_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  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27731
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.67
_diffrn_reflns_theta_min         2.68
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_T_max  0.9296
_exptl_absorpt_correction_T_min  0.8970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.334
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3867
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0282
_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)+(0.0611P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0824
_reflns_number_gt                3412
_reflns_number_total             3867
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2671.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_cell_volume        2046.0(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223944
_cod_database_fobs_code          2223944
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl2 0.400074(15) 0.86812(5) 0.57272(2) 0.02093(10) Uani d . 1 . .
N N1 0.86727(6) 0.62429(16) 0.08751(8) 0.0176(2) Uani d D 1 . .
H H1N 0.8461 0.6094 0.0269 0.021 Uiso calc RD 1 . .
O O1 0.72464(5) 0.5375(2) 0.15456(8) 0.0373(3) Uani d . 1 . .
O O2 0.74328(5) 0.47101(18) 0.02079(7) 0.0314(3) Uani d . 1 . .
H H2 0.7020 0.4421 0.0003 0.047 Uiso calc R 1 . .
O O3 1.02593(5) 0.77466(16) 0.07980(7) 0.0269(2) Uani d . 1 . .
H H3 1.0420 0.7892 0.0369 0.040 Uiso calc R 1 . .
O O4 0.93315(5) 0.66689(17) -0.03641(7) 0.0312(3) Uani d . 1 . .
C C1 0.93284(6) 0.67693(19) 0.11849(9) 0.0185(3) Uani d . 1 . .
C C2 0.96772(7) 0.6960(2) 0.21350(10) 0.0225(3) Uani d . 1 . .
H H2A 1.0144 0.7289 0.2358 0.027 Uiso calc R 1 . .
C C3 0.93390(8) 0.6665(2) 0.27580(10) 0.0259(3) Uani d . 1 . .
H H3A 0.9572 0.6793 0.3413 0.031 Uiso calc R 1 . .
C C4 0.86538(7) 0.6179(2) 0.24171(10) 0.0234(3) Uani d . 1 . .
H H4 0.8412 0.6016 0.2835 0.028 Uiso calc R 1 . .
C C5 0.83310(7) 0.59365(19) 0.14648(9) 0.0194(3) Uani d . 1 . .
C C6 0.76021(7) 0.5313(2) 0.10756(10) 0.0224(3) Uani d . 1 . .
C C7 0.96393(7) 0.7065(2) 0.04423(9) 0.0210(3) Uani d . 1 . .
C C11 0.55437(6) 0.66485(18) 0.39734(9) 0.0170(3) Uani d . 1 . .
C C12 0.52686(7) 0.65541(19) 0.30102(9) 0.0194(3) Uani d . 1 . .
H H12A 0.4804 0.6830 0.2695 0.023 Uiso calc R 1 . .
C C13 0.56847(7) 0.6047(2) 0.25084(9) 0.0220(3) Uani d . 1 . .
H H13 0.5505 0.6010 0.1844 0.026 Uiso calc R 1 . .
C C14 0.63629(7) 0.5591(2) 0.29749(9) 0.0202(3) Uani d . 1 . .
H H14A 0.6647 0.5235 0.2635 0.024 Uiso calc R 1 . .
C C15 0.66136(6) 0.56671(19) 0.39429(9) 0.0173(3) Uani d . 1 . .
C C16 0.73154(6) 0.51806(19) 0.45933(9) 0.0201(3) Uani d . 1 . .
C C17 0.51949(6) 0.71815(19) 0.46516(9) 0.0189(3) Uani d . 1 . .
N N2 0.62003(6) 0.62153(15) 0.43989(7) 0.0162(2) Uani d D 1 . .
H H2N 0.6370 0.6296 0.5014 0.019 Uiso calc RD 1 . .
O O11 0.74741(5) 0.55571(16) 0.54219(7) 0.0281(2) Uani d . 1 . .
O O12 0.76850(5) 0.43135(16) 0.41724(7) 0.0260(2) Uani d . 1 . .
H H12 0.8064 0.4033 0.4568 0.039 Uiso calc R 1 . .
O O13 0.54906(5) 0.69891(16) 0.54842(7) 0.0269(2) Uani d . 1 . .
O O14 0.45750(5) 0.78176(16) 0.42371(7) 0.0244(2) Uani d . 1 . .
H H14 0.4400 0.8075 0.4643 0.037 Uiso calc R 1 . .
O O30 0.77087(6) 0.63026(17) 0.86620(9) 0.0391(3) Uani d . 1 . .
C C31 0.81624(8) 0.4065(2) 0.78336(11) 0.0325(3) Uani d . 1 . .
H H31A 0.8598 0.4523 0.8271 0.049 Uiso calc R 1 . .
H H31B 0.8139 0.4325 0.7190 0.049 Uiso calc R 1 . .
H H31C 0.8118 0.2646 0.7917 0.049 Uiso calc R 1 . .
C C32 0.76014(7) 0.5135(2) 0.80203(11) 0.0271(3) Uani d . 1 . .
C C33 0.68937(8) 0.4701(3) 0.73731(13) 0.0398(4) Uani d . 1 . .
H H33A 0.6597 0.4538 0.7741 0.060 Uiso calc R 1 . .
H H33B 0.6893 0.3488 0.7024 0.060 Uiso calc R 1 . .
H H33C 0.6730 0.5797 0.6933 0.060 Uiso calc R 1 . .
Cl Cl1 0.903216(16) 0.33503(5) 0.55619(2) 0.02480(11) Uani d . 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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C5 . . 121.98(11) ?
C1 N1 H1N . . 119.0 ?
C5 N1 H1N . . 119.0 ?
C6 O2 H2 . . 109.5 ?
C7 O3 H3 . . 109.5 ?
N1 C1 C2 . . 120.07(13) ?
N1 C1 C7 . . 115.80(12) ?
C2 C1 C7 . . 124.11(12) ?
C1 C2 C3 . . 119.26(13) ?
C1 C2 H2A . . 120.4 ?
C3 C2 H2A . . 120.4 ?
C2 C3 C4 . . 119.53(13) ?
C2 C3 H3A . . 120.2 ?
C4 C3 H3A . . 120.2 ?
C5 C4 C3 . . 119.25(13) ?
C5 C4 H4 . . 120.4 ?
C3 C4 H4 . . 120.4 ?
N1 C5 C4 . . 119.83(12) ?
N1 C5 C6 . . 119.40(12) ?
C4 C5 C6 . . 120.77(13) ?
O1 C6 O2 . . 127.04(13) ?
O1 C6 C5 . . 121.27(13) ?
O2 C6 C5 . . 111.69(12) ?
O4 C7 O3 . . 127.38(13) ?
O4 C7 C1 . . 120.99(12) ?
O3 C7 C1 . . 111.63(12) ?
N2 C11 C12 . . 119.10(12) ?
N2 C11 C17 . . 112.96(11) ?
C12 C11 C17 . . 127.94(12) ?
C11 C12 C13 . . 118.80(12) ?
C11 C12 H12A . . 120.6 ?
C13 C12 H12A . . 120.6 ?
C12 C13 C14 . . 120.46(12) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C15 C14 C13 . . 118.71(12) ?
C15 C14 H14A . . 120.6 ?
C13 C14 H14A . . 120.6 ?
N2 C15 C14 . . 118.96(12) ?
N2 C15 C16 . . 112.85(11) ?
C14 C15 C16 . . 128.19(12) ?
O11 C16 O12 . . 127.34(12) ?
O11 C16 C15 . . 119.41(12) ?
O12 C16 C15 . . 113.22(12) ?
O13 C17 O14 . . 127.23(12) ?
O13 C17 C11 . . 119.68(12) ?
O14 C17 C11 . . 113.10(11) ?
C15 N2 C11 . . 123.93(11) ?
C15 N2 H2N . . 118.0 ?
C11 N2 H2N . . 118.0 ?
C16 O12 H12 . . 109.5 ?
C17 O14 H14 . . 109.5 ?
C32 C31 H31A . . 109.5 ?
C32 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
C32 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
O30 C32 C31 . . 121.94(14) ?
O30 C32 C33 . . 121.25(15) ?
C31 C32 C33 . . 116.81(14) ?
C32 C33 H33A . . 109.5 ?
C32 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
C32 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
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 C1 . 1.3467(17) ?
N1 C5 . 1.3484(18) ?
N1 H1N . 0.8800 ?
O1 C6 . 1.2040(18) ?
O2 C6 . 1.3087(18) ?
O2 H2 . 0.8400 ?
O3 C7 . 1.3147(17) ?
O3 H3 . 0.8400 ?
O4 C7 . 1.2036(17) ?
C1 C2 . 1.3829(19) ?
C1 C7 . 1.5045(19) ?
C2 C3 . 1.385(2) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.396(2) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.381(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.5052(19) ?
C11 N2 . 1.3433(17) ?
C11 C12 . 1.3790(19) ?
C11 C17 . 1.5052(18) ?
C12 C13 . 1.392(2) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.394(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.3834(19) ?
C14 H14A . 0.9500 ?
C15 N2 . 1.3421(17) ?
C15 C16 . 1.5057(18) ?
C16 O11 . 1.2149(17) ?
C16 O12 . 1.3085(17) ?
C17 O13 . 1.2103(17) ?
C17 O14 . 1.3132(16) ?
N2 H2N . 0.8800 ?
O12 H12 . 0.8400 ?
O14 H14 . 0.8400 ?
O30 C32 . 1.2167(19) ?
C31 C32 . 1.498(2) ?
C31 H31A . 0.9800 ?
C31 H31B . 0.9800 ?
C31 H31C . 0.9800 ?
C32 C33 . 1.506(2) ?
C33 H33A . 0.9800 ?
C33 H33B . 0.9800 ?
C33 H33C . 0.9800 ?
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
O2 H2 Cl2 2_645 0.84 2.11 2.9469(13) 170.8
O3 H3 Cl1 2_755 0.84 2.14 2.9727(13) 171.5
O12 H12 Cl1 . 0.84 2.13 2.9696(15) 179.3
O14 H14 Cl2 . 0.84 2.14 2.9775(12) 177.2
N1 H1N O30 1_554 0.88 2.42 3.277(2) 166.3
N1 H1N O2 . 0.88 2.34 2.6685(16) 102.5
N1 H1N O4 . 0.88 2.39 2.7195(16) 102.8
N2 H2N O11 . 0.88 2.25 2.6365(17) 106.2
N2 H2N O13 . 0.88 2.26 2.6392(16) 105.9
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
C5 N1 C1 C2 . . . . 1.76(19) ?
C5 N1 C1 C7 . . . . -179.77(12) ?
N1 C1 C2 C3 . . . . -2.1(2) ?
C7 C1 C2 C3 . . . . 179.60(13) ?
C1 C2 C3 C4 . . . . 0.1(2) ?
C2 C3 C4 C5 . . . . 2.1(2) ?
C1 N1 C5 C4 . . . . 0.54(19) ?
C1 N1 C5 C6 . . . . -178.85(11) ?
C3 C4 C5 N1 . . . . -2.5(2) ?
C3 C4 C5 C6 . . . . 176.92(12) ?
N1 C5 C6 O1 . . . . -166.16(14) ?
C4 C5 C6 O1 . . . . 14.5(2) ?
N1 C5 C6 O2 . . . . 14.67(18) ?
C4 C5 C6 O2 . . . . -164.72(13) ?
N1 C1 C7 O4 . . . . -6.70(19) ?
C2 C1 C7 O4 . . . . 171.71(14) ?
N1 C1 C7 O3 . . . . 174.26(11) ?
C2 C1 C7 O3 . . . . -7.33(19) ?
N2 C11 C12 C13 . . . . -1.17(19) ?
C17 C11 C12 C13 . . . . 179.30(12) ?
C11 C12 C13 C14 . . . . 1.71(19) ?
C12 C13 C14 C15 . . . . -0.4(2) ?
C13 C14 C15 N2 . . . . -1.37(19) ?
C13 C14 C15 C16 . . . . 177.90(12) ?
N2 C15 C16 O11 . . . . -9.64(18) ?
C14 C15 C16 O11 . . . . 171.05(13) ?
N2 C15 C16 O12 . . . . 168.43(11) ?
C14 C15 C16 O12 . . . . -10.9(2) ?
N2 C11 C17 O13 . . . . -7.56(18) ?
C12 C11 C17 O13 . . . . 172.00(13) ?
N2 C11 C17 O14 . . . . 172.82(11) ?
C12 C11 C17 O14 . . . . -7.62(19) ?
C14 C15 N2 C11 . . . . 2.01(19) ?
C16 C15 N2 C11 . . . . -177.37(11) ?
C12 C11 N2 C15 . . . . -0.71(19) ?
C17 C11 N2 C15 . . . . 178.89(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655928
