#------------------------------------------------------------------------------
#$Date: 2015-11-12 08:45:24 +0200 (Thu, 12 Nov 2015) $
#$Revision: 170264 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/32/7223236.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7223236
loop_
_publ_author_name
'Ananyev, Ivan V.'
'Bushmarinov, Ivan S.'
'Ushakov, Ivan E.'
'Aitkulova, Liliya I.'
'Lyssenko, Konstantin A.'
_publ_section_title
;
 Tuning of double-well potential of short strong hydrogen bond by ionic
 interactions in alkali metal hydrodicarboxylates
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA19870D
_journal_year                    2015
_chemical_formula_moiety         'C4 H3 Na O4'
_chemical_formula_sum            'C4 H3 Na O4'
_chemical_formula_weight         138.05
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-09-24 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                82.252(3)
_cell_angle_beta                 88.021(3)
_cell_angle_gamma                67.127(2)
_cell_formula_units_Z            2
_cell_length_a                   5.3534(7)
_cell_length_b                   6.6038(9)
_cell_length_c                   7.9446(11)
_cell_measurement_reflns_used    192
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     256.37(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector''
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3424
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.988
_diffrn_reflns_theta_min         2.588
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_description       prism
_exptl_crystal_F_000             140
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0497P)²+0.0629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0953
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1317
_reflns_number_total             1498
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c5ra19870d2.cif
_cod_data_source_block           300
_cod_database_code               7223236
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.958
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
Na1 Na 0.03086(9) 0.76338(9) 1.39236(6) 0.02520(16) Uani 1 1 d
O3 O 0.25857(18) 0.84526(16) 0.61491(11) 0.0268(2) Uani 1 1 d
O1 O 0.44435(18) 0.72879(17) 1.25260(11) 0.0264(2) Uani 1 1 d
O4 O 0.68208(17) 0.66352(16) 0.53413(10) 0.0237(2) Uani 1 1 d
O2 O 0.83985(18) 0.71266(17) 1.14360(11) 0.0264(2) Uani 1 1 d
C1 C 0.6068(2) 0.73027(18) 1.12460(14) 0.0185(2) Uani 1 1 d
C2 C 0.4778(2) 0.75658(19) 0.95588(14) 0.0197(2) Uani 1 1 d
C3 C 0.6226(2) 0.7401(2) 0.81609(14) 0.0196(2) Uani 1 1 d
C4 C 0.5071(2) 0.75410(19) 0.64438(14) 0.0179(2) Uani 1 1 d
H1 H 0.544(4) 0.705(4) 1.365(3) 0.065(7) Uiso 1 1 d
H2 H 0.283(4) 0.778(3) 0.951(2) 0.034(4) Uiso 1 1 d
H3 H 0.811(4) 0.718(3) 0.822(2) 0.040(5) Uiso 1 1 d
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'
Na Na 0.0362 0.0249 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O2 Na1 O1 91.93(4) 1_455 .
O2 Na1 O4 83.76(3) 1_455 1_456
O1 Na1 O4 160.40(4) . 1_456
O2 Na1 O3 171.04(4) 1_455 1_556
O1 Na1 O3 80.79(4) . 1_556
O4 Na1 O3 104.83(4) 1_456 1_556
O2 Na1 O3 95.66(4) 1_455 2_577
O1 Na1 O3 109.34(4) . 2_577
O4 Na1 O3 90.14(4) 1_456 2_577
O3 Na1 O3 81.98(4) 1_556 2_577
O2 Na1 O4 92.40(3) 1_455 2_667
O1 Na1 O4 78.73(3) . 2_667
O4 Na1 O4 82.35(4) 1_456 2_667
O3 Na1 O4 91.29(3) 1_556 2_667
O3 Na1 O4 168.33(4) 2_577 2_667
O2 Na1 Na1 135.79(4) 1_455 2_578
O1 Na1 Na1 96.60(3) . 2_578
O4 Na1 Na1 99.81(3) 1_456 2_578
O3 Na1 Na1 41.23(2) 1_556 2_578
O3 Na1 Na1 40.75(2) 2_577 2_578
O4 Na1 Na1 131.81(3) 2_667 2_578
O2 Na1 Na1 87.71(3) 1_455 2_568
O1 Na1 Na1 117.57(3) . 2_568
O4 Na1 Na1 43.35(2) 1_456 2_568
O3 Na1 Na1 100.26(3) 1_556 2_568
O3 Na1 Na1 132.83(3) 2_577 2_568
O4 Na1 Na1 39.01(2) 2_667 2_568
Na1 Na1 Na1 124.74(3) 2_578 2_568
O2 Na1 H1 113.9(5) 1_455 .
O1 Na1 H1 22.9(5) . .
O4 Na1 H1 149.6(5) 1_456 .
O3 Na1 H1 59.6(5) 1_556 .
O3 Na1 H1 111.2(5) 2_577 .
O4 Na1 H1 72.8(5) 2_667 .
Na1 Na1 H1 84.7(5) 2_578 .
Na1 Na1 H1 110.1(5) 2_568 .
C4 O3 Na1 123.78(8) . 1_554
C4 O3 Na1 127.86(8) . 2_577
Na1 O3 Na1 98.02(3) 1_554 2_577
C1 O1 Na1 157.51(7) . .
C1 O1 H1 110.4(12) . .
Na1 O1 H1 92.0(12) . .
C4 O4 Na1 131.90(8) . 1_654
C4 O4 Na1 116.17(7) . 2_667
Na1 O4 Na1 97.65(4) 1_654 2_667
C1 O2 Na1 126.33(8) . 1_655
O2 C1 O1 122.90(10) . .
O2 C1 C2 123.64(10) . .
O1 C1 C2 113.46(10) . .
C3 C2 C1 120.55(11) . .
C3 C2 H2 120.9(11) . .
C1 C2 H2 118.5(11) . .
C2 C3 C4 122.87(11) . .
C2 C3 H3 120.4(12) . .
C4 C3 H3 116.7(12) . .
O3 C4 O4 123.92(10) . .
O3 C4 C3 121.07(10) . .
O4 C4 C3 115.01(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Na1 O2 2.3765(10) 1_455
Na1 O1 2.3855(10) .
Na1 O4 2.4086(10) 1_456
Na1 O3 2.4133(10) 1_556
Na1 O3 2.4364(11) 2_577
Na1 O4 2.6269(11) 2_667
Na1 Na1 3.6607(11) 2_578
Na1 Na1 3.7928(12) 2_568
Na1 H1 2.63(2) .
O3 C4 1.2443(14) .
O3 Na1 2.4132(10) 1_554
O3 Na1 2.4365(11) 2_577
O1 C1 1.3165(14) .
O1 H1 1.02(2) .
O4 C4 1.2851(14) .
O4 Na1 2.4086(10) 1_654
O4 Na1 2.6269(11) 2_667
O2 C1 1.2202(14) .
O2 Na1 2.3765(10) 1_655
C1 C2 1.4870(15) .
C2 C3 1.3241(17) .
C2 H2 0.996(17) .
C3 C4 1.4938(15) .
C3 H3 0.963(19) .
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_site_symmetry_1
Na1 O2 C1 O1 -16.69(17) 1_655
Na1 O2 C1 C2 162.97(8) 1_655
Na1 O1 C1 O2 172.02(16) .
Na1 O1 C1 C2 -7.7(3) .
O2 C1 C2 C3 6.75(19) .
O1 C1 C2 C3 -173.55(11) .
C1 C2 C3 C4 176.96(10) .
Na1 O3 C4 O4 23.27(17) 1_554
Na1 O3 C4 O4 -113.83(12) 2_577
Na1 O3 C4 C3 -155.74(9) 1_554
Na1 O3 C4 C3 67.16(15) 2_577
Na1 O4 C4 O3 111.76(12) 1_654
Na1 O4 C4 O3 -118.44(11) 2_667
Na1 O4 C4 C3 -69.17(13) 1_654
Na1 O4 C4 C3 60.63(11) 2_667
C2 C3 C4 O3 21.61(19) .
C2 C3 C4 O4 -157.49(12) .
