#------------------------------------------------------------------------------
#$Date: 2015-11-12 08:45:24 +0200 (Thu, 12 Nov 2015) $
#$Revision: 170264 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/32/7223235.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_7223235
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                82.191(2)
_cell_angle_beta                 87.998(2)
_cell_angle_gamma                67.167(2)
_cell_formula_units_Z            2
_cell_length_a                   5.3472(6)
_cell_length_b                   6.5737(7)
_cell_length_c                   7.9466(8)
_cell_measurement_reflns_used    108
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     255.01(5)
_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      250(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0180
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 1.000
_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            3412
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.588
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.966
_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    1.798
_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         0.438
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0493P)²+0.0675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1344
_reflns_number_total             1492
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c5ra19870d2.cif
_cod_data_source_block           250
_cod_database_code               7223235
_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 0.03122(9) 0.76318(8) 1.39227(6) 0.02085(15) Uani 1 1 d
O3 O 0.25833(17) 0.84548(15) 0.61501(11) 0.0226(2) Uani 1 1 d
O1 O 0.44458(17) 0.72840(16) 1.25279(10) 0.0221(2) Uani 1 1 d
O4 O 0.68283(17) 0.66281(15) 0.53371(10) 0.01954(19) Uani 1 1 d
O2 O 0.84102(17) 0.71259(16) 1.14335(11) 0.0221(2) Uani 1 1 d
C1 C 0.6072(2) 0.73004(18) 1.12478(13) 0.0156(2) Uani 1 1 d
C2 C 0.4781(2) 0.75641(18) 0.95574(13) 0.0169(2) Uani 1 1 d
C3 C 0.6234(2) 0.74032(19) 0.81582(13) 0.0163(2) Uani 1 1 d
C4 C 0.5076(2) 0.75381(18) 0.64419(13) 0.0151(2) Uani 1 1 d
H1 H 0.539(4) 0.704(3) 1.363(3) 0.054(6) Uiso 1 1 d
H2 H 0.285(3) 0.782(3) 0.954(2) 0.027(4) Uiso 1 1 d
H3 H 0.810(4) 0.716(3) 0.823(2) 0.037(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 91.79(3) 1_455 .
O2 Na1 O4 83.89(3) 1_455 1_456
O1 Na1 O4 160.35(4) . 1_456
O2 Na1 O3 170.99(4) 1_455 1_556
O1 Na1 O3 80.91(3) . 1_556
O4 Na1 O3 104.74(3) 1_456 1_556
O2 Na1 O3 95.59(3) 1_455 2_577
O1 Na1 O3 109.53(4) . 2_577
O4 Na1 O3 90.00(3) 1_456 2_577
O3 Na1 O3 82.02(3) 1_556 2_577
O2 Na1 O4 92.59(3) 1_455 2_667
O1 Na1 O4 78.68(3) . 2_667
O4 Na1 O4 82.36(3) 1_456 2_667
O3 Na1 O4 91.15(3) 1_556 2_667
O3 Na1 O4 168.16(4) 2_577 2_667
O2 Na1 Na1 135.82(3) 1_455 2_578
O1 Na1 Na1 96.76(3) . 2_578
O4 Na1 Na1 99.68(3) 1_456 2_578
O3 Na1 Na1 41.17(2) 1_556 2_578
O3 Na1 Na1 40.86(2) 2_577 2_578
O4 Na1 Na1 131.59(3) 2_667 2_578
O2 Na1 Na1 87.91(3) 1_455 2_568
O1 Na1 Na1 117.62(3) . 2_568
O4 Na1 Na1 43.26(2) 1_456 2_568
O3 Na1 Na1 100.13(3) 1_556 2_568
O3 Na1 Na1 132.59(3) 2_577 2_568
O4 Na1 Na1 39.10(2) 2_667 2_568
Na1 Na1 Na1 124.47(3) 2_578 2_568
O2 Na1 H1 113.3(5) 1_455 .
O1 Na1 H1 22.4(5) . .
O4 Na1 H1 149.8(5) 1_456 .
O3 Na1 H1 60.2(5) 1_556 .
O3 Na1 H1 111.6(5) 2_577 .
O4 Na1 H1 72.6(5) 2_667 .
Na1 Na1 H1 85.2(5) 2_578 .
Na1 Na1 H1 110.1(5) 2_568 .
C4 O3 Na1 123.57(7) . 1_554
C4 O3 Na1 128.03(8) . 2_577
Na1 O3 Na1 97.98(3) 1_554 2_577
C1 O1 Na1 157.49(7) . .
C1 O1 H1 111.3(12) . .
Na1 O1 H1 91.1(12) . .
C4 O4 Na1 131.86(7) . 1_654
C4 O4 Na1 116.07(7) . 2_667
Na1 O4 Na1 97.64(3) 1_654 2_667
C1 O2 Na1 126.05(7) . 1_655
O2 C1 O1 123.07(10) . .
O2 C1 C2 123.44(10) . .
O1 C1 C2 113.49(9) . .
C3 C2 C1 120.53(10) . .
C3 C2 H2 122.4(10) . .
C1 C2 H2 117.1(10) . .
C2 C3 C4 122.72(10) . .
C2 C3 H3 119.8(12) . .
C4 C3 H3 117.4(11) . .
O3 C4 O4 124.00(10) . .
O3 C4 C3 120.95(10) . .
O4 C4 C3 115.04(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Na1 O2 2.3748(9) 1_455
Na1 O1 2.3815(10) .
Na1 O4 2.4032(9) 1_456
Na1 O3 2.4126(9) 1_556
Na1 O3 2.4275(10) 2_577
Na1 O4 2.6111(10) 2_667
Na1 Na1 3.6522(10) 2_578
Na1 Na1 3.7766(10) 2_568
Na1 H1 2.60(2) .
O3 C4 1.2463(13) .
O3 Na1 2.4126(9) 1_554
O3 Na1 2.4276(10) 2_577
O1 C1 1.3166(13) .
O1 H1 0.99(2) .
O4 C4 1.2872(13) .
O4 Na1 2.4032(9) 1_654
O4 Na1 2.6111(10) 2_667
O2 C1 1.2228(14) .
O2 Na1 2.3748(9) 1_655
C1 C2 1.4897(15) .
C2 C3 1.3260(16) .
C2 H2 0.981(16) .
C3 C4 1.4951(15) .
C3 H3 0.952(18) .
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 -16.51(16) 1_655
Na1 O2 C1 C2 163.13(8) 1_655
Na1 O1 C1 O2 171.84(15) .
Na1 O1 C1 C2 -7.8(3) .
O2 C1 C2 C3 6.65(18) .
O1 C1 C2 C3 -173.67(11) .
C1 C2 C3 C4 176.80(10) .
Na1 O3 C4 O4 23.12(15) 1_554
Na1 O3 C4 O4 -113.82(11) 2_577
Na1 O3 C4 C3 -156.06(8) 1_554
Na1 O3 C4 C3 66.99(13) 2_577
Na1 O4 C4 O3 111.84(11) 1_654
Na1 O4 C4 O3 -118.59(10) 2_667
Na1 O4 C4 C3 -68.93(12) 1_654
Na1 O4 C4 C3 60.64(11) 2_667
C2 C3 C4 O3 21.91(17) .
C2 C3 C4 O4 -157.34(11) .
