#------------------------------------------------------------------------------
#$Date: 2015-11-12 08:45:24 +0200 (Thu, 12 Nov 2015) $
#$Revision: 170264 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/32/7223232.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_7223232
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                82.0400(10)
_cell_angle_beta                 87.9280(10)
_cell_angle_gamma                67.2300(10)
_cell_formula_units_Z            2
_cell_length_a                   5.32570(10)
_cell_length_b                   6.48800(10)
_cell_length_c                   7.9340(2)
_cell_measurement_reflns_used    797
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     250.298(9)
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.967
_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  0.0372
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            49023
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         63.070
_diffrn_reflns_theta_min         2.593
_exptl_absorpt_coefficient_mu    0.235
_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    1.832
_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         0.605
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         8020
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0530P)²+0.0095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0926
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6955
_reflns_number_total             8020
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c5ra19870d2.cif
_cod_data_source_block           100
_cod_database_code               7223232
_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   0.946
_shelx_estimated_absorpt_t_max   0.957
_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 -0.46778(2) 0.76256(2) 1.39219(2) 0.00965(2) Uani 1 1 d
O4 O 0.18522(4) 0.66059(3) 0.53367(2) 0.00944(3) Uani 1 1 d
O2 O 0.34314(4) 0.71231(4) 1.14284(2) 0.01073(3) Uani 1 1 d
O1 O -0.05456(4) 0.72751(4) 1.25351(2) 0.01062(3) Uani 1 1 d
O3 O -0.24113(4) 0.84542(3) 0.61474(2) 0.01065(3) Uani 1 1 d
C4 C 0.00901(4) 0.75320(4) 0.64385(3) 0.00766(3) Uani 1 1 d
C3 C 0.12557(4) 0.74049(4) 0.81515(3) 0.00868(3) Uani 1 1 d
C2 C -0.02178(5) 0.75609(4) 0.95613(3) 0.00868(3) Uani 1 1 d
C1 C 0.10808(4) 0.72973(4) 1.12475(3) 0.00788(3) Uani 1 1 d
H2 H -0.2122(18) 0.7765(16) 0.9500(12) 0.0215(19) Uiso 1 1 d
H3 H 0.3294(18) 0.7086(16) 0.8234(12) 0.022(2) Uiso 1 1 d
H1 H 0.050(2) 0.7032(19) 1.3693(14) 0.039(3) 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'
O O 0.0106 0.0060 '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'
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 91.628(8) 1_455 .
O2 Na1 O4 84.229(8) 1_455 1_456
O1 Na1 O4 160.225(9) . 1_456
O2 Na1 O3 170.820(10) 1_455 1_556
O1 Na1 O3 80.932(8) . 1_556
O4 Na1 O3 104.574(8) 1_456 1_556
O2 Na1 O3 95.400(8) 1_455 2_477
O1 Na1 O3 110.059(9) . 2_477
O4 Na1 O3 89.607(8) 1_456 2_477
O3 Na1 O3 82.245(8) 1_556 2_477
O2 Na1 O4 92.900(8) 1_455 2_567
O1 Na1 O4 78.553(8) . 2_567
O4 Na1 O4 82.347(7) 1_456 2_567
O3 Na1 O4 90.893(7) 1_556 2_567
O3 Na1 O4 167.806(9) 2_477 2_567
O2 Na1 Na1 135.848(8) 1_455 2_478
O1 Na1 Na1 97.075(7) . 2_478
O4 Na1 Na1 99.347(7) 1_456 2_478
O3 Na1 Na1 41.140(5) 1_556 2_478
O3 Na1 Na1 41.105(5) 2_477 2_478
O4 Na1 Na1 131.249(7) 2_567 2_478
O2 Na1 Na1 88.302(7) 1_455 2_468
O1 Na1 Na1 117.800(8) . 2_468
O4 Na1 Na1 42.937(5) 1_456 2_468
O3 Na1 Na1 99.899(7) 1_556 2_468
O3 Na1 Na1 131.868(8) 2_477 2_468
O4 Na1 Na1 39.410(5) 2_567 2_468
Na1 Na1 Na1 123.863(7) 2_478 2_468
O2 Na1 H1 114.3(2) 1_455 .
O1 Na1 H1 23.5(2) . .
O4 Na1 H1 149.0(2) 1_456 .
O3 Na1 H1 59.1(2) 1_556 .
O3 Na1 H1 111.8(2) 2_477 .
O4 Na1 H1 72.5(2) 2_567 .
Na1 Na1 H1 84.6(3) 2_478 .
Na1 Na1 H1 110.0(2) 2_468 .
C4 O4 Na1 131.727(16) . 1_654
C4 O4 Na1 116.215(15) . 2_567
Na1 O4 Na1 97.653(8) 1_654 2_567
C1 O2 Na1 125.682(16) . 1_655
C1 O1 Na1 157.203(15) . .
C1 O1 H1 110.1(6) . .
Na1 O1 H1 92.6(6) . .
C4 O3 Na1 123.589(15) . 1_554
C4 O3 Na1 128.309(17) . 2_477
Na1 O3 Na1 97.755(8) 1_554 2_477
O3 C4 O4 124.13(2) . .
O3 C4 C3 121.034(19) . .
O4 C4 C3 114.833(19) . .
C2 C3 C4 122.34(2) . .
C2 C3 H3 119.9(5) . .
C4 C3 H3 117.6(5) . .
C3 C2 C1 120.17(2) . .
C3 C2 H2 120.3(6) . .
C1 C2 H2 119.5(6) . .
O2 C1 O1 123.04(2) . .
O2 C1 C2 123.47(2) . .
O1 C1 C2 113.486(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Na1 O2 2.3687(2) 1_455
Na1 O1 2.3690(2) .
Na1 O4 2.3883(2) 1_456
Na1 O3 2.4047(2) 1_556
Na1 O3 2.4064(2) 2_477
Na1 O4 2.5626(2) 2_567
Na1 Na1 3.6242(3) 2_478
Na1 Na1 3.7283(3) 2_468
Na1 H1 2.636(10) .
O4 C4 1.2866(3) .
O4 Na1 2.3882(2) 1_654
O4 Na1 2.5626(2) 2_567
O2 C1 1.2246(3) .
O2 Na1 2.3688(2) 1_655
O1 C1 1.3174(3) .
O1 H1 1.052(11) .
O3 C4 1.2462(3) .
O3 Na1 2.4047(2) 1_554
O3 Na1 2.4064(2) 2_477
C4 C3 1.4932(3) .
C3 C2 1.3355(3) .
C3 H3 1.026(9) .
C2 C1 1.4864(3) .
C2 H2 0.973(8) .
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 O3 C4 O4 22.60(3) 1_554
Na1 O3 C4 O4 -114.38(2) 2_477
Na1 O3 C4 C3 -156.536(17) 1_554
Na1 O3 C4 C3 66.49(3) 2_477
Na1 O4 C4 O3 111.85(2) 1_654
Na1 O4 C4 O3 -118.51(2) 2_567
Na1 O4 C4 C3 -68.97(3) 1_654
Na1 O4 C4 C3 60.67(2) 2_567
O3 C4 C3 C2 22.27(4) .
O4 C4 C3 C2 -156.94(2) .
C4 C3 C2 C1 176.62(2) .
Na1 O2 C1 O1 -16.33(3) 1_655
Na1 O2 C1 C2 163.473(17) 1_655
Na1 O1 C1 O2 171.66(3) .
Na1 O1 C1 C2 -8.16(6) .
C3 C2 C1 O2 6.34(4) .
C3 C2 C1 O1 -173.84(2) .
