#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/08/2010886.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2010886
loop_
_publ_author_name
'Muir, Kenneth W.'
'Macdonald, Alistair'
'Murray, Alistair'
'Macdonald, Allison'
_publ_section_title
;
 Sodium dihydrogen tris(cyclopropanecarboxylate)
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              534
_journal_page_last               535
_journal_paper_doi               10.1107/S0108270100001128
_journal_volume                  56
_journal_year                    2000
_chemical_formula_iupac          'NaH2 (C4 H5 O2 )3 '
_chemical_formula_moiety         'Na 1+, C4 H5 O2 1-, 2C4 H6 O2'
_chemical_formula_sum            'C12 H17 Na O6'
_chemical_formula_weight         280.25
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 101.151(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3629(7)
_cell_length_b                   6.7768(4)
_cell_length_c                   16.9374(12)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23.8
_cell_measurement_theta_min      18.3
_cell_volume                     1392.24(15)
_computing_cell_refinement       'CAD4 Express'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo , 1995)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'WINGX  (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full .768
_diffrn_measured_fraction_theta_max .768
_diffrn_measurement_device_type  'Enraf Nonius CAD4 diffractometer'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .018
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4477
_diffrn_reflns_theta_full        29.95
_diffrn_reflns_theta_max         27
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 184
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .132
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      1.34
_exptl_crystal_density_method    'flotation in heptane/1,2-dichloroethane'
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          .49
_exptl_crystal_size_mid          .21
_exptl_crystal_size_min          .11
_refine_diff_density_max         .26
_refine_diff_density_min         -.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3357
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_gt           .042
_refine_ls_shift/su_max          .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0556P)²+0.352P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .125
_reflns_number_gt                2175
_reflns_number_total             3357
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1395.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0556P)^2^+0.352P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0556P)^2^+0.352P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2010886
_cod_database_fobs_code          2010886
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Na1 .25832(6) .26125(9) .75806(4) .0424(2) Uani d . 1 . . Na
O11 .43738(10) .16489(18) .74499(8) .0480(3) Uani d . 1 . . O
O12 .38710(11) -.11652(19) .68568(8) .0549(4) Uani d . 1 . . O
C11 .45721(14) .0169(2) .70601(10) .0370(4) Uani d . 1 . . C
C12 .56531(15) -.0031(3) .68133(12) .0482(5) Uani d . 1 . . C
H12 .5751 -.1226 .6509 .058 Uiso calc R 1 . . H
C13 .66778(16) .0764(4) .73416(15) .0661(6) Uani d . 1 . . C
H13A .6601 .1396 .7842 .079 Uiso calc R 1 . . H
H13B .7357 .0029 .7366 .079 Uiso calc R 1 . . H
C14 .62219(17) .1788(4) .65887(13) .0614(6) Uani d . 1 . . C
H14A .662 .1682 .615 .074 Uiso calc R 1 . . H
H14B .5864 .3049 .6626 .074 Uiso calc R 1 . . H
O21 .23813(10) -.00417(17) .84734(7) .0432(3) Uani d . 1 . . O
O22 .11666(13) .1073(2) .91684(9) .0671(5) Uani d . 1 . . O
H2 .107(2) .207(5) .8780(17) .107(10) Uiso d . 1 . . H
C21 .18570(14) -.0252(2) .90041(10) .0388(4) Uani d . 1 . . C
C22 .19714(15) -.2029(3) .95117(10) .0452(4) Uani d . 1 . . C
H22 .2424 -.3079 .9345 .054 Uiso calc R 1 . . H
C23 .20379(19) -.1860(3) 1.04051(11) .0584(5) Uani d . 1 . . C
H23A .2538 -.2739 1.0751 .07 Uiso calc R 1 . . H
H23B .1969 -.0556 1.0626 .07 Uiso calc R 1 . . H
C24 .10587(18) -.2725(4) .99023(11) .0595(6) Uani d . 1 . . C
H24A .0384 -.1956 .9815 .071 Uiso calc R 1 . . H
H24B .0954 -.4138 .994 .071 Uiso calc R 1 . . H
O31 .12784(16) .0376(2) .66665(9) .0677(4) Uani d . 1 . . O
O32 -.04255(14) -.0599(3) .66820(13) .0839(6) Uani d . 1 . . O
H3 -.011(3) -.145(5) .7033(18) .121(12) Uiso d . 1 . . H
C31 .0311(3) .0585(3) .64551(13) .0683(7) Uani d . 1 . . C
C32 .0045(4) .2197(7) .5908(3) .0438(10) Uani d P .5 A 1 C
H32A .0645 .2941 .5744 .053 Uiso calc PR .5 A 1 H
C33 -.1061(4) .1989(8) .5310(3) .0599(12) Uani d P .5 A 1 C
H33A -.1122 .2599 .4786 .072 Uiso calc PR .5 A 1 H
H33B -.146 .0757 .5311 .072 Uiso calc PR .5 A 1 H
C34 -.1004(4) .3288(7) .6005(3) .0556(11) Uani d P .5 A 1 C
H34A -.137 .2857 .6432 .067 Uiso calc PR .5 A 1 H
H34B -.1033 .4699 .5907 .067 Uiso calc PR .5 A 1 H
C32B -.0573(6) .2146(10) .5948(4) .0827(19) Uani d P .5 A 2 C
H32B -.1349 .2039 .5992 .099 Uiso calc PR .5 A 2 H
C33B -.0323(8) .2610(9) .5186(3) .100(2) Uani d P .5 A 2 C
H33C -.0934 .2834 .4741 .119 Uiso calc PR .5 A 2 H
H33D .0317 .1987 .504 .119 Uiso calc PR .5 A 2 H
C34B -.0133(5) .4075(7) .5843(3) .0745(13) Uani d P .5 A 2 C
H34C .0622 .4346 .6104 .089 Uiso calc PR .5 A 2 H
H34D -.063 .5194 .5805 .089 Uiso calc PR .5 A 2 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na .0362 .0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O12 Na1 O11 2_556 . 160.70(6) yes
O12 Na1 O21 2_556 . 80.02(5) ?
O11 Na1 O21 . . 93.77(5) ?
O12 Na1 O21 2_556 2_556 101.21(5) ?
O11 Na1 O21 . 2_556 87.77(5) ?
O21 Na1 O21 . 2_556 171.08(5) yes
O12 Na1 O31 2_556 . 90.70(6) ?
O11 Na1 O31 . . 106.08(6) ?
O21 Na1 O31 . . 78.66(5) ?
O21 Na1 O31 2_556 . 92.47(5) ?
O12 Na1 O31 2_556 2_556 85.94(6) ?
O11 Na1 O31 . 2_556 79.16(5) ?
O21 Na1 O31 . 2_556 110.67(5) ?
O21 Na1 O31 2_556 2_556 78.25(5) ?
O31 Na1 O31 . 2_556 169.29(6) yes
O12 Na1 Na1 2_556 2_546 110.21(5) ?
O11 Na1 Na1 . 2_546 76.12(4) ?
O21 Na1 Na1 . 2_546 44.79(3) ?
O21 Na1 Na1 2_556 2_546 127.60(5) ?
O31 Na1 Na1 . 2_546 47.86(5) ?
O31 Na1 Na1 2_556 2_546 142.70(5) ?
O12 Na1 Na1 2_556 2_556 68.98(4) ?
O11 Na1 Na1 . 2_556 108.15(4) ?
O21 Na1 Na1 . 2_556 141.90(4) ?
O21 Na1 Na1 2_556 2_556 44.71(3) ?
O31 Na1 Na1 . 2_556 121.94(5) ?
O31 Na1 Na1 2_556 2_556 47.42(4) ?
Na1 Na1 Na1 2_546 2_556 169.60(5) ?
C11 O11 Na1 . . 123.69(11) ?
C11 O12 Na1 . 2_546 133.42(11) ?
O11 C11 O12 . . 121.84(15) ?
O11 C11 C12 . . 120.10(15) ?
O12 C11 C12 . . 118.05(15) ?
C11 C12 C13 . . 120.14(17) ?
C11 C12 C14 . . 119.22(17) ?
C13 C12 C14 . . 58.35(14) ?
C14 C13 C12 . . 60.87(14) ?
C13 C14 C12 . . 60.78(15) ?
C21 O21 Na1 . . 133.77(11) ?
C21 O21 Na1 . 2_546 124.26(11) ?
Na1 O21 Na1 . 2_546 90.50(4) ?
O21 C21 O22 . . 122.81(16) ?
O21 C21 C22 . . 121.62(16) ?
O22 C21 C22 . . 115.57(15) ?
C21 C22 C24 . . 121.55(17) ?
C21 C22 C23 . . 120.41(17) ?
C24 C22 C23 . . 58.42(13) ?
C24 C23 C22 . . 60.34(13) ?
C23 C24 C22 . . 61.24(13) ?
C31 O31 Na1 . . 126.97(16) ?
C31 O31 Na1 . 2_546 131.93(14) ?
Na1 O31 Na1 . 2_546 84.72(6) ?
O31 C31 O32 . . 123.2(2) ?
O31 C31 C32 . . 112.2(3) ?
O32 C31 C32 . . 124.5(3) ?
O31 C31 C32B . . 139.8(3) ?
O32 C31 C32B . . 96.8(3) ?
C32 C31 C32B . . 28.4(2) ?
C31 C32 C34 . . 113.2(4) ?
C31 C32 C33 . . 114.8(4) ?
C34 C32 C33 . . 56.7(3) ?
C34 C33 C32 . . 61.2(3) ?
C33 C34 C32 . . 62.1(3) ?
C33B C32B C34B . . 62.2(4) ?
C33B C32B C31 . . 112.3(7) ?
C34B C32B C31 . . 114.9(5) ?
C32B C33B C34B . . 59.6(4) ?
C32B C34B C33B . . 58.2(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Na1 O12 2_556 2.3429(14) yes
Na1 O11 . 2.3590(14) yes
Na1 O21 . 2.3939(13) yes
Na1 O21 2_556 2.3972(13) yes
Na1 O31 . 2.5162(18) yes
Na1 O31 2_556 2.534(2) yes
Na1 Na1 2_546 3.4024(2) ?
Na1 Na1 2_556 3.4024(2) ?
O11 C11 . 1.251(2) ?
O12 C11 . 1.254(2) ?
O12 Na1 2_546 2.3429(14) ?
C11 C12 . 1.482(2) ?
C12 C13 . 1.502(3) ?
C12 C14 . 1.504(3) ?
C13 C14 . 1.465(3) ?
O21 C21 . 1.214(2) ?
O21 Na1 2_546 2.3972(13) ?
O22 C21 . 1.305(2) ?
C21 C22 . 1.471(2) ?
C22 C24 . 1.491(3) ?
C22 C23 . 1.504(2) ?
C23 C24 . 1.461(3) ?
O31 C31 . 1.189(3) ?
O31 Na1 2_546 2.534(2) ?
O32 C31 . 1.325(3) ?
C31 C32 . 1.429(5) ?
C31 C32B . 1.639(7) ?
C32 C34 . 1.529(6) ?
C32 C33 . 1.542(6) ?
C33 C34 . 1.459(7) ?
C32B C33B . 1.419(10) ?
C32B C34B . 1.440(8) ?
C33B C34B . 1.477(8) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O22 H2 O12 2_556 .93(3) 1.62(3) 2.5475(18) 171(3)
O32 H3 O11 2_546 .86(3) 1.72(3) 2.567(2) 167(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O12 Na1 O11 C11 2_556 . 142.71(16)
O21 Na1 O11 C11 . . 72.43(14)
O21 Na1 O11 C11 2_556 . -98.77(14)
O31 Na1 O11 C11 . . -6.84(15)
O31 Na1 O11 C11 2_556 . -177.23(14)
Na1 Na1 O11 C11 2_546 . 30.92(13)
Na1 Na1 O11 C11 2_556 . -139.20(13)
Na1 O11 C11 O12 . . -16.2(2)
Na1 O11 C11 C12 . . 162.76(13)
Na1 O12 C11 O11 2_546 . -29.3(3)
Na1 O12 C11 C12 2_546 . 151.69(14)
O11 C11 C12 C13 . . 33.4(3)
O12 C11 C12 C13 . . -147.62(19)
O11 C11 C12 C14 . . -34.9(3)
O12 C11 C12 C14 . . 144.12(18)
C11 C12 C13 C14 . . -107.8(2)
C11 C12 C14 C13 . . 109.3(2)
O12 Na1 O21 C21 2_556 . -9.52(16)
O11 Na1 O21 C21 . . 152.07(16)
O21 Na1 O21 C21 2_556 . -108.3(3)
O31 Na1 O21 C21 . . -102.27(17)
O31 Na1 O21 C21 2_556 . 72.24(17)
Na1 Na1 O21 C21 2_546 . -141.99(18)
Na1 Na1 O21 C21 2_556 . 25.9(2)
O12 Na1 O21 Na1 2_556 2_546 132.46(6)
O11 Na1 O21 Na1 . 2_546 -65.95(5)
O21 Na1 O21 Na1 2_556 2_546 33.7(2)
O31 Na1 O21 Na1 . 2_546 39.71(5)
O31 Na1 O21 Na1 2_556 2_546 -145.77(6)
Na1 Na1 O21 Na1 2_556 2_546 167.92(8)
Na1 O21 C21 O22 . . 5.0(3)
Na1 O21 C21 O22 2_546 . -126.86(17)
Na1 O21 C21 C22 . . -174.44(12)
Na1 O21 C21 C22 2_546 . 53.7(2)
O21 C21 C22 C24 . . -153.56(18)
O22 C21 C22 C24 . . 27.0(3)
O21 C21 C22 C23 . . 137.05(19)
O22 C21 C22 C23 . . -42.4(3)
C21 C22 C23 C24 . . 110.6(2)
C21 C22 C24 C23 . . -108.6(2)
O12 Na1 O31 C31 2_556 . 23.32(19)
O11 Na1 O31 C31 . . -166.32(18)
O21 Na1 O31 C31 . . 103.00(18)
O21 Na1 O31 C31 2_556 . -77.93(18)
O31 Na1 O31 C31 2_556 . -48.2(2)
Na1 Na1 O31 C31 2_546 . 140.4(2)
Na1 Na1 O31 C31 2_556 . -42.2(2)
O12 Na1 O31 Na1 2_556 2_546 -117.06(5)
O11 Na1 O31 Na1 . 2_546 53.30(5)
O21 Na1 O31 Na1 . 2_546 -37.38(4)
O21 Na1 O31 Na1 2_556 2_546 141.69(5)
O31 Na1 O31 Na1 2_556 2_546 171.39(17)
Na1 Na1 O31 Na1 2_556 2_546 177.47(5)
Na1 O31 C31 O32 . . -112.1(2)
Na1 O31 C31 O32 2_546 . 9.3(4)
Na1 O31 C31 C32 . . 70.3(3)
Na1 O31 C31 C32 2_546 . -168.3(2)
Na1 O31 C31 C32B . . 61.9(6)
Na1 O31 C31 C32B 2_546 . -176.7(5)
O31 C31 C32 C34 . . -145.5(3)
O32 C31 C32 C34 . . 37.0(5)
C32B C31 C32 C34 . . 23.0(6)
O31 C31 C32 C33 . . 151.9(3)
O32 C31 C32 C33 . . -25.7(5)
C32B C31 C32 C33 . . -39.6(7)
C31 C32 C33 C34 . . 102.4(4)
C31 C32 C34 C33 . . -105.3(5)
O31 C31 C32B C33B . . 51.3(8)
O32 C31 C32B C33B . . -133.8(5)
C32 C31 C32B C33B . . 34.6(7)
O31 C31 C32B C34B . . -17.3(9)
O32 C31 C32B C34B . . 157.6(6)
C32 C31 C32B C34B . . -33.9(5)
C31 C32B C33B C34B . . -107.4(5)
C31 C32B C34B C33B . . 103.2(7)
