# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1427273'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H3 K O4'
_chemical_formula_sum            'C4 H3 K O4'
_chemical_formula_weight         154.16

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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2337(4)
_cell_length_b                   6.7932(5)
_cell_length_c                   7.4636(5)
_cell_angle_alpha                67.8720(10)
_cell_angle_beta                 72.6380(10)
_cell_angle_gamma                63.2960(10)
_cell_volume                     258.35(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    723
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_F_000             156
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.951
_shelx_estimated_absorpt_T_min   0.770
_shelx_estimated_absorpt_T_max   0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_T_max  0.833
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            66424
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.502
_diffrn_reflns_theta_max         62.288
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             8081
_reflns_number_gt                6928
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)²+0.0194P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8081
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0611
_refine_ls_wR_factor_gt          0.0583
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.09514(5) 1.20993(5) 0.48046(4) 0.01155(3) Uani 1 1 d . . . . .
O1 O 0.42216(5) 1.30058(5) 0.33125(3) 0.00954(3) Uani 1 1 d . . . . .
O3 O 0.72812(4) 1.16239(5) 0.94163(4) 0.01012(3) Uani 1 1 d . . . . .
O4 O 0.32428(4) 1.33453(4) 1.01922(3) 0.00922(3) Uani 1 1 d . . . . .
C1 C 0.26215(5) 1.26008(5) 0.48275(4) 0.00748(3) Uani 1 1 d . . . . .
C2 C 0.28574(5) 1.27287(5) 0.67092(4) 0.00853(3) Uani 1 1 d . . . . .
C4 C 0.51935(5) 1.25208(5) 0.90190(4) 0.00724(3) Uani 1 1 d . . . . .
C3 C 0.48830(5) 1.26414(5) 0.70627(4) 0.00812(3) Uani 1 1 d . . . . .
H2 H 0.145(2) 1.2766(18) 0.7679(16) 0.022(2) Uiso 1 1 d . . . . .
H3 H 0.6347(18) 1.2578(17) 0.6054(15) 0.020(2) Uiso 1 1 d . . . . .
H1 H 0.372(3) 1.308(3) 0.189(3) 0.073(6) Uiso 1 1 d . . . . .
K1 K 0.92290(2) 1.19155(2) 0.20083(2) 0.00896(1) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.2385(4) . ?
O2 K1 2.6792(3) 1_455 ?
O2 K1 2.8876(3) 2_676 ?
O1 C1 1.2993(4) . ?
O1 K1 2.8092(3) . ?
O1 H1 1.172(17) . ?
O3 C4 1.2387(4) . ?
O3 K1 2.6764(3) 1_556 ?
O3 K1 2.7366(3) 2_776 ?
O4 C4 1.2966(4) . ?
O4 K1 2.8651(3) 1_456 ?
O4 K1 2.9163(3) 2_686 ?
C1 C2 1.4928(4) . ?
C2 C3 1.3369(4) . ?
C2 H2 0.955(11) . ?
C4 C3 1.4968(4) . ?
C3 H3 0.990(10) . ?
K1 O3 2.6764(3) 1_554 ?
K1 O2 2.6792(3) 1_655 ?
K1 O3 2.7365(3) 2_776 ?
K1 O4 2.8651(3) 1_654 ?
K1 O2 2.8876(3) 2_676 ?
K1 O4 2.9163(3) 2_686 ?

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
_geom_angle_publ_flag
C1 O2 K1 134.87(2) . 1_455 ?
C1 O2 K1 110.85(2) . 2_676 ?
K1 O2 K1 103.764(10) 1_455 2_676 ?
C1 O1 K1 143.55(2) . . ?
C1 O1 H1 111.1(9) . . ?
K1 O1 H1 97.3(9) . . ?
C4 O3 K1 132.82(2) . 1_556 ?
C4 O3 K1 120.768(19) . 2_776 ?
K1 O3 K1 105.612(9) 1_556 2_776 ?
C4 O4 K1 130.38(2) . 1_456 ?
C4 O4 K1 105.341(18) . 2_686 ?
K1 O4 K1 101.023(8) 1_456 2_686 ?
O2 C1 O1 124.21(3) . . ?
O2 C1 C2 118.69(3) . . ?
O1 C1 C2 117.09(2) . . ?
C3 C2 C1 123.95(3) . . ?
C3 C2 H2 122.9(6) . . ?
C1 C2 H2 113.0(6) . . ?
O3 C4 O4 124.50(3) . . ?
O3 C4 C3 118.12(3) . . ?
O4 C4 C3 117.38(2) . . ?
C2 C3 C4 123.61(3) . . ?
C2 C3 H3 122.3(6) . . ?
C4 C3 H3 114.0(6) . . ?
O3 K1 O2 175.916(8) 1_554 1_655 ?
O3 K1 O3 74.388(9) 1_554 2_776 ?
O2 K1 O3 107.033(9) 1_655 2_776 ?
O3 K1 O1 70.811(8) 1_554 . ?
O2 K1 O1 105.801(9) 1_655 . ?
O3 K1 O1 131.218(8) 2_776 . ?
O3 K1 O4 112.390(9) 1_554 1_654 ?
O2 K1 O4 71.690(8) 1_655 1_654 ?
O3 K1 O4 75.525(9) 2_776 1_654 ?
O1 K1 O4 150.028(9) . 1_654 ?
O3 K1 O2 100.539(9) 1_554 2_676 ?
O2 K1 O2 76.236(10) 1_655 2_676 ?
O3 K1 O2 77.154(10) 2_776 2_676 ?
O1 K1 O2 76.816(8) . 2_676 ?
O4 K1 O2 128.818(8) 1_654 2_676 ?
O3 K1 O4 74.756(9) 1_554 2_686 ?
O2 K1 O4 106.702(9) 1_655 2_686 ?
O3 K1 O4 128.000(9) 2_776 2_686 ?
O1 K1 O4 73.176(8) . 2_686 ?
O4 K1 O4 78.977(9) 1_654 2_686 ?
O2 K1 O4 149.489(8) 2_676 2_686 ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
K1 O2 C1 O1 -7.07(5) 1_455 . . . ?
K1 O2 C1 O1 130.52(3) 2_676 . . . ?
K1 O2 C1 C2 173.69(2) 1_455 . . . ?
K1 O2 C1 C2 -48.72(3) 2_676 . . . ?
K1 O1 C1 O2 -131.05(3) . . . . ?
K1 O1 C1 C2 48.20(5) . . . . ?
O2 C1 C2 C3 161.46(3) . . . . ?
O1 C1 C2 C3 -17.83(5) . . . . ?
K1 O3 C4 O4 -21.60(5) 1_556 . . . ?
K1 O3 C4 O4 146.57(2) 2_776 . . . ?
K1 O3 C4 C3 159.21(2) 1_556 . . . ?
K1 O3 C4 C3 -32.62(4) 2_776 . . . ?
K1 O4 C4 O3 -115.46(3) 1_456 . . . ?
K1 O4 C4 O3 124.97(3) 2_686 . . . ?
K1 O4 C4 C3 63.74(3) 1_456 . . . ?
K1 O4 C4 C3 -55.83(3) 2_686 . . . ?
C1 C2 C3 C4 -173.30(3) . . . . ?
O3 C4 C3 C2 153.89(3) . . . . ?
O4 C4 C3 C2 -25.36(4) . . . . ?

_refine_diff_density_max         0.827
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.094

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_150
_database_code_depnum_ccdc_archive 'CCDC 1427274'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H3 K O4'
_chemical_formula_sum            'C4 H3 K O4'
_chemical_formula_weight         154.16

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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2351(4)
_cell_length_b                   6.8144(5)
_cell_length_c                   7.4635(5)
_cell_angle_alpha                67.9990(10)
_cell_angle_beta                 72.7000(10)
_cell_angle_gamma                63.3370(10)
_cell_volume                     259.54(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    191
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.973
_exptl_crystal_F_000             156
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.946
_shelx_estimated_absorpt_T_min   0.771
_shelx_estimated_absorpt_T_max   0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_T_max  0.843
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3419
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0111
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.980
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1514
_reflns_number_gt                1439
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0317P)²+0.1235P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1514
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0625
_refine_ls_wR_factor_gt          0.0612
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.09604(16) 1.20943(16) 0.48009(13) 0.01744(18) Uani 1 1 d . . . . .
O1 O 0.42162(15) 1.30111(15) 0.33114(12) 0.01441(17) Uani 1 1 d . . . . .
O3 O 0.72736(15) 1.16222(15) 0.94147(12) 0.01508(17) Uani 1 1 d . . . . .
O4 O 0.32426(15) 1.33472(15) 1.01860(12) 0.01379(17) Uani 1 1 d . . . . .
C1 C 0.2619(2) 1.26010(18) 0.48255(16) 0.0117(2) Uani 1 1 d . . . . .
C2 C 0.2863(2) 1.2729(2) 0.67052(16) 0.0128(2) Uani 1 1 d . . . . .
C4 C 0.5193(2) 1.25182(18) 0.90171(15) 0.01125(19) Uani 1 1 d . . . . .
C3 C 0.4877(2) 1.26442(19) 0.70589(16) 0.0121(2) Uani 1 1 d . . . . .
H2 H 0.149(3) 1.281(3) 0.765(3) 0.028(5) Uiso 1 1 d . . . . .
H3 H 0.630(3) 1.259(3) 0.608(3) 0.025(5) Uiso 1 1 d . . . . .
H1 H 0.376(5) 1.308(5) 0.188(4) 0.089(10) Uiso 1 1 d . . . . .
K1 K 0.92293(4) 1.19132(4) 0.20054(3) 0.01403(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.2350(13) . ?
O2 K1 2.6805(9) 1_455 ?
O2 K1 2.8980(10) 2_676 ?
O1 C1 1.3004(13) . ?
O1 K1 2.8135(9) . ?
O1 H1 1.17(3) . ?
O3 C4 1.2354(14) . ?
O3 K1 2.6780(8) 1_556 ?
O3 K1 2.7397(9) 2_776 ?
O4 C4 1.2965(13) . ?
O4 K1 2.8705(9) 1_456 ?
O4 K1 2.9250(9) 2_686 ?
C1 C2 1.4933(15) . ?
C2 C3 1.3303(15) . ?
C2 H2 0.925(19) . ?
C4 C3 1.4982(14) . ?
C3 H3 0.961(18) . ?
K1 O3 2.6780(8) 1_554 ?
K1 O2 2.6805(9) 1_655 ?
K1 O3 2.7397(9) 2_776 ?
K1 O4 2.8705(9) 1_654 ?
K1 O2 2.8980(10) 2_676 ?
K1 O4 2.9250(9) 2_686 ?

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
_geom_angle_publ_flag
C1 O2 K1 134.97(7) . 1_455 ?
C1 O2 K1 111.04(7) . 2_676 ?
K1 O2 K1 103.75(3) 1_455 2_676 ?
C1 O1 K1 143.45(7) . . ?
C1 O1 H1 112.1(14) . . ?
K1 O1 H1 96.1(14) . . ?
C4 O3 K1 132.83(7) . 1_556 ?
C4 O3 K1 121.01(7) . 2_776 ?
K1 O3 K1 105.39(3) 1_556 2_776 ?
C4 O4 K1 130.20(7) . 1_456 ?
C4 O4 K1 105.60(6) . 2_686 ?
K1 O4 K1 101.23(3) 1_456 2_686 ?
O2 C1 O1 124.23(10) . . ?
O2 C1 C2 118.92(10) . . ?
O1 C1 C2 116.85(10) . . ?
C3 C2 C1 124.17(10) . . ?
C3 C2 H2 121.9(11) . . ?
C1 C2 H2 113.9(11) . . ?
O3 C4 O4 124.59(10) . . ?
O3 C4 C3 118.23(10) . . ?
O4 C4 C3 117.19(9) . . ?
C2 C3 C4 123.70(10) . . ?
C2 C3 H3 122.6(10) . . ?
C4 C3 H3 113.6(10) . . ?
O3 K1 O2 175.90(3) 1_554 1_655 ?
O3 K1 O3 74.61(3) 1_554 2_776 ?
O2 K1 O3 106.78(3) 1_655 2_776 ?
O3 K1 O1 70.81(3) 1_554 . ?
O2 K1 O1 105.81(3) 1_655 . ?
O3 K1 O1 131.42(3) 2_776 . ?
O3 K1 O4 112.41(3) 1_554 1_654 ?
O2 K1 O4 71.68(3) 1_655 1_654 ?
O3 K1 O4 75.56(3) 2_776 1_654 ?
O1 K1 O4 149.81(3) . 1_654 ?
O3 K1 O2 100.49(3) 1_554 2_676 ?
O2 K1 O2 76.25(3) 1_655 2_676 ?
O3 K1 O2 77.14(3) 2_776 2_676 ?
O1 K1 O2 76.80(3) . 2_676 ?
O4 K1 O2 129.01(3) 1_654 2_676 ?
O3 K1 O4 74.96(3) 1_554 2_686 ?
O2 K1 O4 106.53(3) 1_655 2_686 ?
O3 K1 O4 128.26(3) 2_776 2_686 ?
O1 K1 O4 73.14(2) . 2_686 ?
O4 K1 O4 78.77(3) 1_654 2_686 ?
O2 K1 O4 149.41(3) 2_676 2_686 ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
K1 O2 C1 O1 -7.37(18) 1_455 . . . ?
K1 O2 C1 O1 130.73(10) 2_676 . . . ?
K1 O2 C1 C2 173.54(7) 1_455 . . . ?
K1 O2 C1 C2 -48.35(12) 2_676 . . . ?
K1 O1 C1 O2 -130.41(11) . . . . ?
K1 O1 C1 C2 48.69(16) . . . . ?
O2 C1 C2 C3 161.20(12) . . . . ?
O1 C1 C2 C3 -17.95(17) . . . . ?
K1 O3 C4 O4 -21.67(17) 1_556 . . . ?
K1 O3 C4 O4 146.66(9) 2_776 . . . ?
K1 O3 C4 C3 158.97(7) 1_556 . . . ?
K1 O3 C4 C3 -32.69(13) 2_776 . . . ?
K1 O4 C4 O3 -115.13(11) 1_456 . . . ?
K1 O4 C4 O3 124.83(10) 2_686 . . . ?
K1 O4 C4 C3 64.23(12) 1_456 . . . ?
K1 O4 C4 C3 -55.81(10) 2_686 . . . ?
C1 C2 C3 C4 -173.12(10) . . . . ?
O3 C4 C3 C2 153.62(12) . . . . ?
O4 C4 C3 C2 -25.78(16) . . . . ?

_refine_diff_density_max         0.413
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.063

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_200
_database_code_depnum_ccdc_archive 'CCDC 1427275'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H3 K O4'
_chemical_formula_sum            'C4 H3 K O4'
_chemical_formula_weight         154.16

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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2374(4)
_cell_length_b                   6.8401(4)
_cell_length_c                   7.4662(4)
_cell_angle_alpha                68.1330(10)
_cell_angle_beta                 72.7660(10)
_cell_angle_gamma                63.3940(10)
_cell_volume                     261.08(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    101
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.961
_exptl_crystal_F_000             156
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.941
_shelx_estimated_absorpt_T_min   0.772
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_T_max  0.844
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3431
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0116
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.976
_diffrn_reflns_theta_max         29.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1524
_reflns_number_gt                1432
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0358P)²+0.1017P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1524
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0679
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.09662(17) 1.20919(18) 0.47978(13) 0.0217(2) Uani 1 1 d . . . . .
O1 O 0.42113(16) 1.30143(16) 0.33114(12) 0.01788(18) Uani 1 1 d . . . . .
O3 O 0.72659(16) 1.16219(16) 0.94139(13) 0.01903(19) Uani 1 1 d . . . . .
O4 O 0.32441(15) 1.33451(16) 1.01806(12) 0.01713(18) Uani 1 1 d . . . . .
C1 C 0.2620(2) 1.26002(19) 0.48218(16) 0.0140(2) Uani 1 1 d . . . . .
C2 C 0.2865(2) 1.2728(2) 0.67018(16) 0.0155(2) Uani 1 1 d . . . . .
C4 C 0.5189(2) 1.25202(19) 0.90149(16) 0.0135(2) Uani 1 1 d . . . . .
C3 C 0.4870(2) 1.2644(2) 0.70584(16) 0.0148(2) Uani 1 1 d . . . . .
H2 H 0.149(4) 1.280(3) 0.765(3) 0.039(5) Uiso 1 1 d . . . . .
H3 H 0.631(3) 1.259(3) 0.608(3) 0.031(5) Uiso 1 1 d . . . . .
H1 H 0.373(5) 1.304(5) 0.189(4) 0.089(10) Uiso 1 1 d . . . . .
K1 K 0.92292(4) 1.19119(5) 0.20026(4) 0.01773(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.2336(14) . ?
O2 K1 2.6823(9) 1_455 ?
O2 K1 2.9111(10) 2_676 ?
O1 C1 1.2992(14) . ?
O1 K1 2.8182(9) . ?
O1 H1 1.17(3) . ?
O3 C4 1.2345(14) . ?
O3 K1 2.6796(9) 1_556 ?
O3 K1 2.7462(10) 2_776 ?
O4 C4 1.2940(14) . ?
O4 K1 2.8758(9) 1_456 ?
O4 K1 2.9376(10) 2_686 ?
C1 C2 1.4940(15) . ?
C2 C3 1.3265(16) . ?
C2 H2 0.93(2) . ?
C4 C3 1.4986(15) . ?
C3 H3 0.972(19) . ?
K1 O3 2.6797(9) 1_554 ?
K1 O2 2.6823(9) 1_655 ?
K1 O3 2.7462(10) 2_776 ?
K1 O4 2.8758(9) 1_654 ?
K1 O2 2.9112(10) 2_676 ?
K1 O4 2.9376(10) 2_686 ?

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
_geom_angle_publ_flag
C1 O2 K1 134.95(8) . 1_455 ?
C1 O2 K1 111.20(8) . 2_676 ?
K1 O2 K1 103.73(3) 1_455 2_676 ?
C1 O1 K1 143.35(7) . . ?
C1 O1 H1 110.8(14) . . ?
K1 O1 H1 96.8(14) . . ?
C4 O3 K1 132.81(8) . 1_556 ?
C4 O3 K1 121.26(7) . 2_776 ?
K1 O3 K1 105.19(3) 1_556 2_776 ?
C4 O4 K1 130.20(7) . 1_456 ?
C4 O4 K1 105.69(7) . 2_686 ?
K1 O4 K1 101.40(3) 1_456 2_686 ?
O2 C1 O1 124.34(10) . . ?
O2 C1 C2 118.86(10) . . ?
O1 C1 C2 116.79(10) . . ?
C3 C2 C1 124.26(11) . . ?
C3 C2 H2 122.0(12) . . ?
C1 C2 H2 113.7(12) . . ?
O3 C4 O4 124.61(10) . . ?
O3 C4 C3 118.26(10) . . ?
O4 C4 C3 117.12(10) . . ?
C2 C3 C4 123.86(10) . . ?
C2 C3 H3 123.1(11) . . ?
C4 C3 H3 113.0(11) . . ?
O3 K1 O2 175.87(3) 1_554 1_655 ?
O3 K1 O3 74.81(3) 1_554 2_776 ?
O2 K1 O3 106.59(3) 1_655 2_776 ?
O3 K1 O1 70.81(3) 1_554 . ?
O2 K1 O1 105.78(3) 1_655 . ?
O3 K1 O1 131.57(3) 2_776 . ?
O3 K1 O4 112.41(3) 1_554 1_654 ?
O2 K1 O4 71.72(3) 1_655 1_654 ?
O3 K1 O4 75.59(3) 2_776 1_654 ?
O1 K1 O4 149.67(3) . 1_654 ?
O3 K1 O2 100.44(3) 1_554 2_676 ?
O2 K1 O2 76.27(3) 1_655 2_676 ?
O3 K1 O2 77.05(3) 2_776 2_676 ?
O1 K1 O2 76.81(3) . 2_676 ?
O4 K1 O2 129.13(3) 1_654 2_676 ?
O3 K1 O4 75.18(3) 1_554 2_686 ?
O2 K1 O4 106.33(3) 1_655 2_686 ?
O3 K1 O4 128.54(3) 2_776 2_686 ?
O1 K1 O4 73.14(3) . 2_686 ?
O4 K1 O4 78.60(3) 1_654 2_686 ?
O2 K1 O4 149.38(3) 2_676 2_686 ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
K1 O2 C1 O1 -7.4(2) 1_455 . . . ?
K1 O2 C1 O1 130.90(10) 2_676 . . . ?
K1 O2 C1 C2 173.44(8) 1_455 . . . ?
K1 O2 C1 C2 -48.24(13) 2_676 . . . ?
K1 O1 C1 O2 -129.96(12) . . . . ?
K1 O1 C1 C2 49.20(17) . . . . ?
O2 C1 C2 C3 161.04(12) . . . . ?
O1 C1 C2 C3 -18.17(18) . . . . ?
K1 O3 C4 O4 -22.05(18) 1_556 . . . ?
K1 O3 C4 O4 146.52(9) 2_776 . . . ?
K1 O3 C4 C3 158.89(8) 1_556 . . . ?
K1 O3 C4 C3 -32.54(14) 2_776 . . . ?
K1 O4 C4 O3 -114.73(11) 1_456 . . . ?
K1 O4 C4 O3 124.86(11) 2_686 . . . ?
K1 O4 C4 C3 64.34(13) 1_456 . . . ?
K1 O4 C4 C3 -56.07(11) 2_686 . . . ?
C1 C2 C3 C4 -173.12(10) . . . . ?
O3 C4 C3 C2 153.36(13) . . . . ?
O4 C4 C3 C2 -25.77(17) . . . . ?

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.061

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_250
_database_code_depnum_ccdc_archive 'CCDC 1427276'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H3 K O4'
_chemical_formula_sum            'C4 H3 K O4'
_chemical_formula_weight         154.16

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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2401(3)
_cell_length_b                   6.8687(4)
_cell_length_c                   7.4695(4)
_cell_angle_alpha                68.2700(10)
_cell_angle_beta                 72.8360(10)
_cell_angle_gamma                63.4500(10)
_cell_volume                     262.78(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    95
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.948
_exptl_crystal_F_000             156
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.935
_shelx_estimated_absorpt_T_min   0.773
_shelx_estimated_absorpt_T_max   0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_T_max  0.846
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3452
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_av_R_equivalents  0.0106
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.972
_diffrn_reflns_theta_max         29.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1533
_reflns_number_gt                1440
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+0.0511P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1533
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0697
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.270
_refine_ls_restrained_S_all      1.270
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.09759(17) 1.20886(18) 0.47914(13) 0.0266(2) Uani 1 1 d . . . . .
O1 O 0.42036(16) 1.30179(16) 0.33119(12) 0.02180(19) Uani 1 1 d . . . . .
O3 O 0.72616(16) 1.16240(16) 0.94099(13) 0.02289(19) Uani 1 1 d . . . . .
O4 O 0.32462(15) 1.33469(16) 1.01745(12) 0.02081(18) Uani 1 1 d . . . . .
C1 C 0.2622(2) 1.25983(19) 0.48181(16) 0.0170(2) Uani 1 1 d . . . . .
C2 C 0.2870(2) 1.2724(2) 0.66979(16) 0.0185(2) Uani 1 1 d . . . . .
C4 C 0.5186(2) 1.25166(18) 0.90144(15) 0.0161(2) Uani 1 1 d . . . . .
C3 C 0.4867(2) 1.2643(2) 0.70571(16) 0.0177(2) Uani 1 1 d . . . . .
H2 H 0.148(4) 1.283(3) 0.761(3) 0.040(5) Uiso 1 1 d . . . . .
H3 H 0.632(3) 1.258(3) 0.611(3) 0.037(5) Uiso 1 1 d . . . . .
H1 H 0.371(5) 1.306(5) 0.190(4) 0.102(10) Uiso 1 1 d . . . . .
K1 K 0.92292(4) 1.19104(5) 0.20000(4) 0.02180(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.2314(14) . ?
O2 K1 2.6833(9) 1_455 ?
O2 K1 2.9265(10) 2_676 ?
O1 C1 1.2968(14) . ?
O1 K1 2.8248(9) . ?
O1 H1 1.17(3) . ?
O3 C4 1.2340(14) . ?
O3 K1 2.6813(9) 1_556 ?
O3 K1 2.7527(10) 2_776 ?
O4 C4 1.2926(14) . ?
O4 K1 2.8833(9) 1_456 ?
O4 K1 2.9497(10) 2_686 ?
C1 C2 1.4945(15) . ?
C2 C3 1.3236(16) . ?
C2 H2 0.92(2) . ?
C4 C3 1.4989(14) . ?
C3 H3 0.964(19) . ?
K1 O3 2.6813(9) 1_554 ?
K1 O2 2.6833(9) 1_655 ?
K1 O3 2.7527(10) 2_776 ?
K1 O4 2.8833(9) 1_654 ?
K1 O2 2.9265(10) 2_676 ?
K1 O4 2.9497(10) 2_686 ?

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
_geom_angle_publ_flag
C1 O2 K1 135.09(8) . 1_455 ?
C1 O2 K1 111.32(8) . 2_676 ?
K1 O2 K1 103.68(3) 1_455 2_676 ?
C1 O1 K1 143.19(7) . . ?
C1 O1 H1 110.7(14) . . ?
K1 O1 H1 97.0(14) . . ?
C4 O3 K1 132.79(7) . 1_556 ?
C4 O3 K1 121.40(7) . 2_776 ?
K1 O3 K1 105.02(3) 1_556 2_776 ?
C4 O4 K1 129.90(7) . 1_456 ?
C4 O4 K1 106.00(7) . 2_686 ?
K1 O4 K1 101.58(3) 1_456 2_686 ?
O2 C1 O1 124.31(10) . . ?
O2 C1 C2 118.94(10) . . ?
O1 C1 C2 116.75(10) . . ?
C3 C2 C1 124.40(10) . . ?
C3 C2 H2 123.1(11) . . ?
C1 C2 H2 112.5(11) . . ?
O3 C4 O4 124.70(10) . . ?
O3 C4 C3 118.16(10) . . ?
O4 C4 C3 117.13(10) . . ?
C2 C3 C4 123.89(10) . . ?
C2 C3 H3 124.3(10) . . ?
C4 C3 H3 111.8(10) . . ?
O3 K1 O2 175.96(3) 1_554 1_655 ?
O3 K1 O3 74.98(3) 1_554 2_776 ?
O2 K1 O3 106.37(3) 1_655 2_776 ?
O3 K1 O1 70.87(3) 1_554 . ?
O2 K1 O1 105.82(3) 1_655 . ?
O3 K1 O1 131.65(3) 2_776 . ?
O3 K1 O4 112.35(3) 1_554 1_654 ?
O2 K1 O4 71.68(3) 1_655 1_654 ?
O3 K1 O4 75.73(3) 2_776 1_654 ?
O1 K1 O4 149.49(3) . 1_654 ?
O3 K1 O2 100.45(3) 1_554 2_676 ?
O2 K1 O2 76.32(3) 1_655 2_676 ?
O3 K1 O2 76.94(3) 2_776 2_676 ?
O1 K1 O2 76.78(3) . 2_676 ?
O4 K1 O2 129.32(3) 1_654 2_676 ?
O3 K1 O4 75.34(3) 1_554 2_686 ?
O2 K1 O4 106.14(3) 1_655 2_686 ?
O3 K1 O4 128.87(3) 2_776 2_686 ?
O1 K1 O4 73.12(3) . 2_686 ?
O4 K1 O4 78.42(3) 1_654 2_686 ?
O2 K1 O4 149.29(3) 2_676 2_686 ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
K1 O2 C1 O1 -7.5(2) 1_455 . . . ?
K1 O2 C1 O1 131.22(10) 2_676 . . . ?
K1 O2 C1 C2 173.36(8) 1_455 . . . ?
K1 O2 C1 C2 -47.97(13) 2_676 . . . ?
K1 O1 C1 O2 -129.52(12) . . . . ?
K1 O1 C1 C2 49.68(17) . . . . ?
O2 C1 C2 C3 160.94(12) . . . . ?
O1 C1 C2 C3 -18.31(18) . . . . ?
K1 O3 C4 O4 -21.59(18) 1_556 . . . ?
K1 O3 C4 O4 146.64(9) 2_776 . . . ?
K1 O3 C4 C3 158.82(8) 1_556 . . . ?
K1 O3 C4 C3 -32.94(13) 2_776 . . . ?
K1 O4 C4 O3 -114.73(11) 1_456 . . . ?
K1 O4 C4 O3 124.46(11) 2_686 . . . ?
K1 O4 C4 C3 64.86(12) 1_456 . . . ?
K1 O4 C4 C3 -55.95(10) 2_686 . . . ?
C1 C2 C3 C4 -173.07(10) . . . . ?
O3 C4 C3 C2 153.32(12) . . . . ?
O4 C4 C3 C2 -26.30(17) . . . . ?

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.058

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_300
_database_code_depnum_ccdc_archive 'CCDC 1427277'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H3 K O4'
_chemical_formula_sum            'C4 H3 K O4'
_chemical_formula_weight         154.16

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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2421(4)
_cell_length_b                   6.8981(5)
_cell_length_c                   7.4726(5)
_cell_angle_alpha                68.4070(10)
_cell_angle_beta                 72.9030(10)
_cell_angle_gamma                63.5040(10)
_cell_volume                     264.48(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    95
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.936
_exptl_crystal_F_000             156
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.929
_shelx_estimated_absorpt_T_min   0.775
_shelx_estimated_absorpt_T_max   0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_T_max  0.847
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3476
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_av_R_equivalents  0.0101
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.968
_diffrn_reflns_theta_max         29.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1545
_reflns_number_gt                1430
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0336P)²+0.0687P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1545
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0701
_refine_ls_wR_factor_gt          0.0679
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_restrained_S_all      1.188
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.09845(18) 1.20824(19) 0.47873(14) 0.0319(2) Uani 1 1 d . . . . .
O1 O 0.41987(16) 1.30188(17) 0.33132(12) 0.0259(2) Uani 1 1 d . . . . .
O3 O 0.72534(17) 1.16243(17) 0.94080(13) 0.0272(2) Uani 1 1 d . . . . .
O4 O 0.32460(16) 1.33470(17) 1.01682(12) 0.02441(19) Uani 1 1 d . . . . .
C1 C 0.2621(2) 1.25983(19) 0.48141(16) 0.0197(2) Uani 1 1 d . . . . .
C2 C 0.2870(2) 1.2724(2) 0.66920(16) 0.0219(2) Uani 1 1 d . . . . .
C4 C 0.5184(2) 1.25163(19) 0.90114(16) 0.0188(2) Uani 1 1 d . . . . .
C3 C 0.4861(2) 1.2643(2) 0.70559(16) 0.0210(2) Uani 1 1 d . . . . .
H2 H 0.149(4) 1.282(3) 0.762(3) 0.046(5) Uiso 1 1 d . . . . .
H3 H 0.631(3) 1.258(3) 0.612(3) 0.041(5) Uiso 1 1 d . . . . .
H1 H 0.371(5) 1.305(5) 0.188(4) 0.104(10) Uiso 1 1 d . . . . .
K1 K 0.92288(5) 1.19092(5) 0.19972(4) 0.02608(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.2297(14) . ?
O2 K1 2.6844(9) 1_455 ?
O2 K1 2.9397(11) 2_676 ?
O1 C1 1.2953(14) . ?
O1 K1 2.8294(9) . ?
O1 H1 1.19(3) . ?
O3 C4 1.2316(14) . ?
O3 K1 2.6835(9) 1_556 ?
O3 K1 2.7601(10) 2_776 ?
O4 C4 1.2924(14) . ?
O4 K1 2.8889(10) 1_456 ?
O4 K1 2.9623(10) 2_686 ?
C1 C2 1.4935(15) . ?
C2 C3 1.3217(17) . ?
C2 H2 0.93(2) . ?
C4 C3 1.4990(15) . ?
C3 H3 0.962(19) . ?
K1 O3 2.6835(9) 1_554 ?
K1 O2 2.6844(9) 1_655 ?
K1 O3 2.7601(10) 2_776 ?
K1 O4 2.8889(10) 1_654 ?
K1 O2 2.9397(11) 2_676 ?
K1 O4 2.9623(10) 2_686 ?

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
_geom_angle_publ_flag
C1 O2 K1 135.11(8) . 1_455 ?
C1 O2 K1 111.56(8) . 2_676 ?
K1 O2 K1 103.68(3) 1_455 2_676 ?
C1 O1 K1 143.18(8) . . ?
C1 O1 H1 110.7(14) . . ?
K1 O1 H1 96.8(14) . . ?
C4 O3 K1 132.80(8) . 1_556 ?
C4 O3 K1 121.61(8) . 2_776 ?
K1 O3 K1 104.82(3) 1_556 2_776 ?
C4 O4 K1 129.81(8) . 1_456 ?
C4 O4 K1 106.18(7) . 2_686 ?
K1 O4 K1 101.81(3) 1_456 2_686 ?
O2 C1 O1 124.38(11) . . ?
O2 C1 C2 118.93(11) . . ?
O1 C1 C2 116.67(10) . . ?
C3 C2 C1 124.54(11) . . ?
C3 C2 H2 122.0(12) . . ?
C1 C2 H2 113.4(12) . . ?
O3 C4 O4 124.74(10) . . ?
O3 C4 C3 118.26(10) . . ?
O4 C4 C3 117.00(10) . . ?
C2 C3 C4 124.10(11) . . ?
C2 C3 H3 124.3(11) . . ?
C4 C3 H3 111.5(11) . . ?
O3 K1 O2 175.94(3) 1_554 1_655 ?
O3 K1 O3 75.18(3) 1_554 2_776 ?
O2 K1 O3 106.12(3) 1_655 2_776 ?
O3 K1 O1 70.89(3) 1_554 . ?
O2 K1 O1 105.81(3) 1_655 . ?
O3 K1 O1 131.77(3) 2_776 . ?
O3 K1 O4 112.33(3) 1_554 1_654 ?
O2 K1 O4 71.71(3) 1_655 1_654 ?
O3 K1 O4 75.81(3) 2_776 1_654 ?
O1 K1 O4 149.33(3) . 1_654 ?
O3 K1 O2 100.41(3) 1_554 2_676 ?
O2 K1 O2 76.32(3) 1_655 2_676 ?
O3 K1 O2 76.86(3) 2_776 2_676 ?
O1 K1 O2 76.73(3) . 2_676 ?
O4 K1 O2 129.49(3) 1_654 2_676 ?
O3 K1 O4 75.58(3) 1_554 2_686 ?
O2 K1 O4 105.96(3) 1_655 2_686 ?
O3 K1 O4 129.17(3) 2_776 2_686 ?
O1 K1 O4 73.16(3) . 2_686 ?
O4 K1 O4 78.19(3) 1_654 2_686 ?
O2 K1 O4 149.25(3) 2_676 2_686 ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
K1 O2 C1 O1 -7.9(2) 1_455 . . . ?
K1 O2 C1 O1 131.30(11) 2_676 . . . ?
K1 O2 C1 C2 173.13(8) 1_455 . . . ?
K1 O2 C1 C2 -47.66(13) 2_676 . . . ?
K1 O1 C1 O2 -128.91(12) . . . . ?
K1 O1 C1 C2 50.07(18) . . . . ?
O2 C1 C2 C3 160.62(13) . . . . ?
O1 C1 C2 C3 -18.41(19) . . . . ?
K1 O3 C4 O4 -21.79(19) 1_556 . . . ?
K1 O3 C4 O4 146.59(10) 2_776 . . . ?
K1 O3 C4 C3 158.71(8) 1_556 . . . ?
K1 O3 C4 C3 -32.91(14) 2_776 . . . ?
K1 O4 C4 O3 -114.35(12) 1_456 . . . ?
K1 O4 C4 O3 124.36(11) 2_686 . . . ?
K1 O4 C4 C3 65.15(13) 1_456 . . . ?
K1 O4 C4 C3 -56.13(11) 2_686 . . . ?
C1 C2 C3 C4 -173.02(11) . . . . ?
O3 C4 C3 C2 153.07(13) . . . . ?
O4 C4 C3 C2 -26.47(18) . . . . ?

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.054

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_100
_database_code_depnum_ccdc_archive 'CCDC 1427278'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H3 Na O4'
_chemical_formula_sum            'C4 H3 Na O4'
_chemical_formula_weight         138.05

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.32570(10)
_cell_length_b                   6.48800(10)
_cell_length_c                   7.9340(2)
_cell_angle_alpha                82.0400(10)
_cell_angle_beta                 87.9280(10)
_cell_angle_gamma                67.2300(10)
_cell_volume                     250.298(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    797
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_F_000             140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.235
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49023
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.593
_diffrn_reflns_theta_max         63.070
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8020
_reflns_number_gt                6955
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+0.0095P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8020
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?

_refine_diff_density_max         0.605
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.085

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_150
_database_code_depnum_ccdc_archive 'CCDC 1427279'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H3 Na O4'
_chemical_formula_sum            'C4 H3 Na O4'
_chemical_formula_weight         138.05

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.3352(5)
_cell_length_b                   6.5195(6)
_cell_length_c                   7.9435(7)
_cell_angle_alpha                82.093(2)
_cell_angle_beta                 87.953(2)
_cell_angle_gamma                67.230(2)
_cell_volume                     252.30(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    149
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_F_000             140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.233
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3386
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.589
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1475
_reflns_number_gt                1352
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²+0.0904P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1475
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.03184(8) 0.76276(7) 1.39214(5) 0.01331(13) Uani 1 1 d . . . . .
O3 O 0.25852(15) 0.84556(14) 0.61470(10) 0.01436(18) Uani 1 1 d . . . . .
O1 O 0.44492(16) 0.72798(14) 1.25327(10) 0.01417(18) Uani 1 1 d . . . . .
O4 O 0.68441(15) 0.66153(13) 0.53353(9) 0.01269(17) Uani 1 1 d . . . . .
O2 O 0.84275(15) 0.71222(14) 1.14298(10) 0.01448(18) Uani 1 1 d . . . . .
C1 C 0.6077(2) 0.72980(16) 1.12454(13) 0.0103(2) Uani 1 1 d . . . . .
C2 C 0.4784(2) 0.75612(17) 0.95590(13) 0.0113(2) Uani 1 1 d . . . . .
C3 C 0.6245(2) 0.74035(17) 0.81529(13) 0.0109(2) Uani 1 1 d . . . . .
C4 C 0.5081(2) 0.75369(17) 0.64409(13) 0.0102(2) Uani 1 1 d . . . . .
H1 H 0.545(4) 0.703(4) 1.368(3) 0.049(6) Uiso 1 1 d . . . . .
H2 H 0.287(3) 0.779(3) 0.954(2) 0.016(4) Uiso 1 1 d . . . . .
H3 H 0.815(4) 0.713(3) 0.822(2) 0.027(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Na1 O2 2.3713(9) 1_455 ?
Na1 O1 2.3735(9) . ?
Na1 O4 2.3932(9) 1_456 ?
Na1 O3 2.4083(9) 1_556 ?
Na1 O3 2.4144(9) 2_577 ?
Na1 O4 2.5816(9) 2_667 ?
Na1 Na1 3.6365(9) 2_578 ?
Na1 Na1 3.7462(9) 2_568 ?
Na1 H1 2.62(2) . ?
O3 C4 1.2463(13) . ?
O3 Na1 2.4083(9) 1_554 ?
O3 Na1 2.4144(9) 2_577 ?
O1 C1 1.3197(12) . ?
O1 H1 1.03(2) . ?
O4 C4 1.2905(12) . ?
O4 Na1 2.3932(9) 1_654 ?
O4 Na1 2.5816(9) 2_667 ?
O2 C1 1.2263(13) . ?
O2 Na1 2.3713(9) 1_655 ?
C1 C2 1.4871(14) . ?
C2 C3 1.3315(14) . ?
C2 H2 0.973(15) . ?
C3 C4 1.4927(14) . ?
C3 H3 0.963(17) . ?

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
_geom_angle_publ_flag
O2 Na1 O1 91.65(3) 1_455 . ?
O2 Na1 O4 84.16(3) 1_455 1_456 ?
O1 Na1 O4 160.31(4) . 1_456 ?
O2 Na1 O3 170.86(4) 1_455 1_556 ?
O1 Na1 O3 80.93(3) . 1_556 ?
O4 Na1 O3 104.61(3) 1_456 1_556 ?
O2 Na1 O3 95.53(3) 1_455 2_577 ?
O1 Na1 O3 109.87(3) . 2_577 ?
O4 Na1 O3 89.70(3) 1_456 2_577 ?
O3 Na1 O3 82.12(3) 1_556 2_577 ?
O2 Na1 O4 92.80(3) 1_455 2_667 ?
O1 Na1 O4 78.63(3) . 2_667 ?
O4 Na1 O4 82.37(3) 1_456 2_667 ?
O3 Na1 O4 90.97(3) 1_556 2_667 ?
O3 Na1 O4 167.86(3) 2_577 2_667 ?
O2 Na1 Na1 135.88(3) 1_455 2_578 ?
O1 Na1 Na1 96.96(3) . 2_578 ?
O4 Na1 Na1 99.42(3) 1_456 2_578 ?
O3 Na1 Na1 41.12(2) 1_556 2_578 ?
O3 Na1 Na1 41.00(2) 2_577 2_578 ?
O4 Na1 Na1 131.32(3) 2_667 2_578 ?
O2 Na1 Na1 88.20(3) 1_455 2_568 ?
O1 Na1 Na1 117.75(3) . 2_568 ?
O4 Na1 Na1 43.08(2) 1_456 2_568 ?
O3 Na1 Na1 99.95(3) 1_556 2_568 ?
O3 Na1 Na1 132.10(3) 2_577 2_568 ?
O4 Na1 Na1 39.285(19) 2_667 2_568 ?
Na1 Na1 Na1 124.03(2) 2_578 2_568 ?
O2 Na1 H1 114.0(5) 1_455 . ?
O1 Na1 H1 23.3(4) . . ?
O4 Na1 H1 149.2(5) 1_456 . ?
O3 Na1 H1 59.4(5) 1_556 . ?
O3 Na1 H1 111.7(5) 2_577 . ?
O4 Na1 H1 72.5(5) 2_667 . ?
Na1 Na1 H1 84.7(5) 2_578 . ?
Na1 Na1 H1 109.9(5) 2_568 . ?
C4 O3 Na1 123.67(7) . 1_554 ?
C4 O3 Na1 128.15(7) . 2_577 ?
Na1 O3 Na1 97.88(3) 1_554 2_577 ?
C1 O1 Na1 157.27(7) . . ?
C1 O1 H1 111.0(11) . . ?
Na1 O1 H1 91.6(11) . . ?
C4 O4 Na1 131.82(7) . 1_654 ?
C4 O4 Na1 116.11(6) . 2_667 ?
Na1 O4 Na1 97.64(3) 1_654 2_667 ?
C1 O2 Na1 125.81(7) . 1_655 ?
O2 C1 O1 122.96(9) . . ?
O2 C1 C2 123.49(9) . . ?
O1 C1 C2 113.56(9) . . ?
C3 C2 C1 120.43(10) . . ?
C3 C2 H2 122.0(9) . . ?
C1 C2 H2 117.5(9) . . ?
C2 C3 C4 122.57(10) . . ?
C2 C3 H3 120.1(11) . . ?
C4 C3 H3 117.3(11) . . ?
O3 C4 O4 123.97(10) . . ?
O3 C4 C3 121.16(9) . . ?
O4 C4 C3 114.87(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Na1 O2 C1 O1 -16.40(14) 1_655 . . . ?
Na1 O2 C1 C2 163.33(7) 1_655 . . . ?
Na1 O1 C1 O2 171.94(13) . . . . ?
Na1 O1 C1 C2 -7.8(2) . . . . ?
O2 C1 C2 C3 6.43(16) . . . . ?
O1 C1 C2 C3 -173.82(10) . . . . ?
C1 C2 C3 C4 176.78(9) . . . . ?
Na1 O3 C4 O4 22.84(14) 1_554 . . . ?
Na1 O3 C4 O4 -114.28(10) 2_577 . . . ?
Na1 O3 C4 C3 -156.25(7) 1_554 . . . ?
Na1 O3 C4 C3 66.63(13) 2_577 . . . ?
Na1 O4 C4 O3 111.86(11) 1_654 . . . ?
Na1 O4 C4 O3 -118.57(10) 2_667 . . . ?
Na1 O4 C4 C3 -69.00(12) 1_654 . . . ?
Na1 O4 C4 C3 60.57(10) 2_667 . . . ?
C2 C3 C4 O3 22.02(16) . . . . ?
C2 C3 C4 O4 -157.15(10) . . . . ?

_refine_diff_density_max         0.513
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.067

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_200
_database_code_depnum_ccdc_archive 'CCDC 1427280'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H3 Na O4'
_chemical_formula_sum            'C4 H3 Na O4'
_chemical_formula_weight         138.05

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.3403(5)
_cell_length_b                   6.5443(6)
_cell_length_c                   7.9451(7)
_cell_angle_alpha                82.134(2)
_cell_angle_beta                 87.969(2)
_cell_angle_gamma                67.198(2)
_cell_volume                     253.51(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    129
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_F_000             140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3391
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.588
_diffrn_reflns_theta_max         29.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1480
_reflns_number_gt                1340
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.0723P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1480
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0871
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.03160(8) 0.76303(8) 1.39218(6) 0.01689(14) Uani 1 1 d . . . . .
O3 O 0.25850(16) 0.84545(14) 0.61479(10) 0.01836(19) Uani 1 1 d . . . . .
O1 O 0.44487(16) 0.72810(15) 1.25318(10) 0.01812(19) Uani 1 1 d . . . . .
O4 O 0.68375(16) 0.66201(14) 0.53372(9) 0.01595(18) Uani 1 1 d . . . . .
O2 O 0.84171(16) 0.71246(15) 1.14324(10) 0.01818(19) Uani 1 1 d . . . . .
C1 C 0.6075(2) 0.72982(17) 1.12468(13) 0.0129(2) Uani 1 1 d . . . . .
C2 C 0.4783(2) 0.75652(17) 0.95588(13) 0.0138(2) Uani 1 1 d . . . . .
C3 C 0.6237(2) 0.74037(18) 0.81573(13) 0.0138(2) Uani 1 1 d . . . . .
C4 C 0.5080(2) 0.75375(17) 0.64417(13) 0.0125(2) Uani 1 1 d . . . . .
H1 H 0.543(4) 0.704(3) 1.368(3) 0.051(6) Uiso 1 1 d . . . . .
H2 H 0.285(3) 0.780(3) 0.952(2) 0.023(4) Uiso 1 1 d . . . . .
H3 H 0.815(4) 0.714(3) 0.822(2) 0.031(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Na1 O2 2.3731(9) 1_455 ?
Na1 O1 2.3766(9) . ?
Na1 O4 2.3985(9) 1_456 ?
Na1 O3 2.4098(9) 1_556 ?
Na1 O3 2.4204(10) 2_577 ?
Na1 O4 2.5947(10) 2_667 ?
Na1 Na1 3.6430(9) 2_578 ?
Na1 Na1 3.7611(10) 2_568 ?
Na1 H1 2.607(19) . ?
O3 C4 1.2464(13) . ?
O3 Na1 2.4098(9) 1_554 ?
O3 Na1 2.4205(10) 2_577 ?
O1 C1 1.3186(13) . ?
O1 H1 1.03(2) . ?
O4 C4 1.2887(13) . ?
O4 Na1 2.3985(9) 1_654 ?
O4 Na1 2.5946(10) 2_667 ?
O2 C1 1.2235(13) . ?
O2 Na1 2.3731(9) 1_655 ?
C1 C2 1.4879(14) . ?
C2 C3 1.3272(15) . ?
C2 H2 0.985(16) . ?
C3 C4 1.4942(14) . ?
C3 H3 0.968(17) . ?

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
_geom_angle_publ_flag
O2 Na1 O1 91.77(3) 1_455 . ?
O2 Na1 O4 84.01(3) 1_455 1_456 ?
O1 Na1 O4 160.28(4) . 1_456 ?
O2 Na1 O3 170.96(4) 1_455 1_556 ?
O1 Na1 O3 80.90(3) . 1_556 ?
O4 Na1 O3 104.66(3) 1_456 1_556 ?
O2 Na1 O3 95.55(3) 1_455 2_577 ?
O1 Na1 O3 109.75(3) . 2_577 ?
O4 Na1 O3 89.85(3) 1_456 2_577 ?
O3 Na1 O3 82.09(3) 1_556 2_577 ?
O2 Na1 O4 92.69(3) 1_455 2_667 ?
O1 Na1 O4 78.63(3) . 2_667 ?
O4 Na1 O4 82.33(3) 1_456 2_667 ?
O3 Na1 O4 91.05(3) 1_556 2_667 ?
O3 Na1 O4 167.99(3) 2_577 2_667 ?
O2 Na1 Na1 135.86(3) 1_455 2_578 ?
O1 Na1 Na1 96.89(3) . 2_578 ?
O4 Na1 Na1 99.54(3) 1_456 2_578 ?
O3 Na1 Na1 41.16(2) 1_556 2_578 ?
O3 Na1 Na1 40.93(2) 2_577 2_578 ?
O4 Na1 Na1 131.46(3) 2_667 2_578 ?
O2 Na1 Na1 88.04(3) 1_455 2_568 ?
O1 Na1 Na1 117.67(3) . 2_568 ?
O4 Na1 Na1 43.13(2) 1_456 2_568 ?
O3 Na1 Na1 100.02(3) 1_556 2_568 ?
O3 Na1 Na1 132.31(3) 2_577 2_568 ?
O4 Na1 Na1 39.20(2) 2_667 2_568 ?
Na1 Na1 Na1 124.22(3) 2_578 2_568 ?
O2 Na1 H1 114.0(5) 1_455 . ?
O1 Na1 H1 23.2(4) . . ?
O4 Na1 H1 149.2(4) 1_456 . ?
O3 Na1 H1 59.4(5) 1_556 . ?
O3 Na1 H1 111.7(5) 2_577 . ?
O4 Na1 H1 72.5(5) 2_667 . ?
Na1 Na1 H1 84.8(5) 2_578 . ?
Na1 Na1 H1 109.9(4) 2_568 . ?
C4 O3 Na1 123.68(7) . 1_554 ?
C4 O3 Na1 128.07(7) . 2_577 ?
Na1 O3 Na1 97.91(3) 1_554 2_577 ?
C1 O1 Na1 157.31(7) . . ?
C1 O1 H1 111.5(11) . . ?
Na1 O1 H1 91.1(11) . . ?
C4 O4 Na1 131.79(7) . 1_654 ?
C4 O4 Na1 116.14(7) . 2_667 ?
Na1 O4 Na1 97.67(3) 1_654 2_667 ?
C1 O2 Na1 126.00(7) . 1_655 ?
O2 C1 O1 122.94(9) . . ?
O2 C1 C2 123.49(10) . . ?
O1 C1 C2 113.57(9) . . ?
C3 C2 C1 120.51(10) . . ?
C3 C2 H2 121.2(9) . . ?
C1 C2 H2 118.2(9) . . ?
C2 C3 C4 122.78(10) . . ?
C2 C3 H3 120.2(11) . . ?
C4 C3 H3 117.0(11) . . ?
O3 C4 O4 123.95(10) . . ?
O3 C4 C3 121.02(9) . . ?
O4 C4 C3 115.02(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Na1 O2 C1 O1 -16.40(15) 1_655 . . . ?
Na1 O2 C1 C2 163.12(7) 1_655 . . . ?
Na1 O1 C1 O2 171.82(14) . . . . ?
Na1 O1 C1 C2 -7.7(2) . . . . ?
O2 C1 C2 C3 6.77(17) . . . . ?
O1 C1 C2 C3 -173.66(10) . . . . ?
C1 C2 C3 C4 176.70(9) . . . . ?
Na1 O3 C4 O4 22.89(15) 1_554 . . . ?
Na1 O3 C4 O4 -114.17(10) 2_577 . . . ?
Na1 O3 C4 C3 -156.13(7) 1_554 . . . ?
Na1 O3 C4 C3 66.81(13) 2_577 . . . ?
Na1 O4 C4 O3 111.85(11) 1_654 . . . ?
Na1 O4 C4 O3 -118.52(10) 2_667 . . . ?
Na1 O4 C4 C3 -69.08(12) 1_654 . . . ?
Na1 O4 C4 C3 60.55(10) 2_667 . . . ?
C2 C3 C4 O3 21.84(17) . . . . ?
C2 C3 C4 O4 -157.26(11) . . . . ?

_refine_diff_density_max         0.486
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.070

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_250
_database_code_depnum_ccdc_archive 'CCDC 1427281'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H3 Na O4'
_chemical_formula_sum            'C4 H3 Na O4'
_chemical_formula_weight         138.05

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.3472(6)
_cell_length_b                   6.5737(7)
_cell_length_c                   7.9466(8)
_cell_angle_alpha                82.191(2)
_cell_angle_beta                 87.998(2)
_cell_angle_gamma                67.167(2)
_cell_volume                     255.01(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    108
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_F_000             140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.230
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3412
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.588
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1492
_reflns_number_gt                1344
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+0.0675P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1492
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?

_refine_diff_density_max         0.438
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.067

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_300
_database_code_depnum_ccdc_archive 'CCDC 1427282'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H3 Na O4'
_chemical_formula_sum            'C4 H3 Na O4'
_chemical_formula_weight         138.05

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.3534(7)
_cell_length_b                   6.6038(9)
_cell_length_c                   7.9446(11)
_cell_angle_alpha                82.252(3)
_cell_angle_beta                 88.021(3)
_cell_angle_gamma                67.127(2)
_cell_volume                     256.37(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    192
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_F_000             140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.229
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3424
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.588
_diffrn_reflns_theta_max         29.988
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1498
_reflns_number_gt                1317
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²+0.0629P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1498
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?

_refine_diff_density_max         0.436
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.064

_shelxl_version_number           2014/6

