#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/44/2014452.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_2014452
loop_
_publ_author_name
'Muir, Kenneth W.'
'Macdonald, Alistair'
'Macdonald, Alan'
_publ_section_title
;
 Sodium 1-carboxycyclopropane-1-carboxylate
 cyclopropane-1,1-dicarboxylic acid monohydrate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m645
_journal_page_last               m647
_journal_paper_doi               10.1107/S0108270104027052
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'Na + , C5 H5 O4 - , C5 H4 O4 , H2 O'
_chemical_formula_moiety         'Na + , C5 H5 O4 - , C5 H4 O4 , H2 O'
_chemical_formula_sum            'C10 H13 Na O9'
_chemical_formula_weight         300.19
_chemical_name_common
;
Sodium trihydrogen bis(cyclopropane-1,1-dicarboxylate) monohydrate
;
_chemical_name_systematic
;
Sodium 1-carboxycyclopropane-1-carboxylate cyclopropane-1,1-dicarboxylic acid
monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                109.44(3)
_cell_angle_beta                 98.64(2)
_cell_angle_gamma                99.57(2)
_cell_formula_units_Z            2
_cell_length_a                   5.2910(13)
_cell_length_b                   10.118(3)
_cell_length_c                   12.895(5)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.7
_cell_measurement_theta_min      18.8
_cell_volume                     626.0(4)
_computing_cell_refinement       CAD-4-EXPRESS
_computing_data_collection       'CAD-4-EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'non-profiled ω'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3932
_diffrn_reflns_theta_full        28
_diffrn_reflns_theta_max         28.0
_diffrn_reflns_theta_min         4.67
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.17
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_gt           0.051
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.075P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.150
_reflns_number_gt                1654
_reflns_number_total             2985
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn1070.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               2014452
_cod_database_fobs_code          2014452
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.1701(2) 0.37779(12) 0.97765(9) 0.0352(3) Uani d . 1 . . Na
O11 0.1927(4) 0.5960(2) 0.76510(18) 0.0356(5) Uani d . 1 . . O
O21 0.4078(4) 0.5633(2) 0.91192(15) 0.0336(5) Uani d . 1 . . O
O31 0.7072(5) 0.2632(2) 0.68504(18) 0.0416(6) Uani d . 1 . . O
O41 0.8106(4) 0.4147(2) 0.86355(15) 0.0301(5) Uani d . 1 . . O
C11 0.4859(5) 0.4464(3) 0.7284(2) 0.0252(6) Uani d . 1 . . C
C21 0.3162(7) 0.3705(4) 0.6105(2) 0.0469(9) Uani d . 1 . . C
H21A 0.3326 0.2744 0.5681 0.056 Uiso calc R 1 . . H
H21B 0.14 0.3859 0.5973 0.056 Uiso calc R 1 . . H
C31 0.5363(7) 0.4912(4) 0.6301(2) 0.0449(9) Uani d . 1 . . C
H31A 0.4955 0.5809 0.6293 0.054 Uiso calc R 1 . . H
H31B 0.6882 0.4692 0.6 0.054 Uiso calc R 1 . . H
C41 0.3651(5) 0.5410(3) 0.8125(2) 0.0237(6) Uani d . 1 . . C
C51 0.6834(5) 0.3729(3) 0.7681(2) 0.0248(6) Uani d . 1 . . C
H11 0.148(10) 0.650(5) 0.813(4) 0.086(16) Uiso d . 1 . . H
H31 0.791(11) 0.222(6) 0.703(4) 0.11(2) Uiso d . 1 . . H
O12 0.6526(4) -0.1338(2) 0.78279(19) 0.0480(6) Uani d . 1 . . O
O22 0.6093(5) 0.0705(3) 0.9017(2) 0.0597(8) Uani d . 1 . . O
O32 0.0016(4) 0.0965(2) 0.68459(17) 0.0434(6) Uani d . 1 . . O
O42 0.2679(4) 0.1867(2) 0.85276(18) 0.0494(6) Uani d . 1 . . O
C12 0.3214(5) -0.0282(3) 0.7212(2) 0.0261(6) Uani d . 1 . . C
C22 0.3379(6) -0.0868(4) 0.5981(2) 0.0412(8) Uani d . 1 . . C
H22A 0.2673 -0.0401 0.5495 0.049 Uiso calc R 1 . . H
H22B 0.4927 -0.1215 0.5811 0.049 Uiso calc R 1 . . H
C32 0.1525(6) -0.1714(3) 0.6373(2) 0.0387(8) Uani d . 1 . . C
H32A 0.1924 -0.2586 0.6444 0.046 Uiso calc R 1 . . H
H32B -0.0329 -0.1772 0.6129 0.046 Uiso calc R 1 . . H
C42 0.5417(6) -0.0353(3) 0.8047(2) 0.0330(6) Uani d . 1 . . C
C52 0.1839(5) 0.0932(3) 0.7549(2) 0.0303(6) Uani d . 1 . . C
H22 0.494(12) 0.131(6) 0.905(5) 0.13(2) Uiso d . 1 . . H
O1W 0.0154(5) 0.2282(2) 1.0885(2) 0.0379(5) Uani d . 1 . . O
H1W -0.094(8) 0.159(4) 1.036(3) 0.048(11) Uiso d . 1 . . H
H2W 0.100(8) 0.180(4) 1.120(3) 0.062(12) Uiso d . 1 . . H
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 1 -8
-1 6 -2
-3 -1 2
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
O42 Na1 O21 . 2_667 89.54(9)
O42 Na1 O41 . 2_667 163.78(9)
O21 Na1 O41 2_667 2_667 74.26(8)
O42 Na1 O41 . 1_455 101.48(9)
O21 Na1 O41 2_667 1_455 155.79(9)
O41 Na1 O41 2_667 1_455 93.90(7)
O42 Na1 O1W . . 91.34(9)
O21 Na1 O1W 2_667 . 89.24(9)
O41 Na1 O1W 2_667 . 87.70(8)
O41 Na1 O1W 1_455 . 111.72(9)
O42 Na1 O21 . . 95.42(9)
O21 Na1 O21 2_667 . 78.33(8)
O41 Na1 O21 2_667 . 82.32(8)
O41 Na1 O21 1_455 . 79.21(8)
O1W Na1 O21 . . 165.77(8)
C41 O11 H11 . . 108(4)
C41 O21 Na1 . 2_667 122.87(17)
C41 O21 Na1 . . 118.33(18)
Na1 O21 Na1 2_667 . 101.67(8)
C51 O31 H31 . . 113(4)
C51 O41 Na1 . 2_667 130.55(17)
C51 O41 Na1 . 1_655 142.66(17)
Na1 O41 Na1 2_667 1_655 86.10(7)
C41 C11 C51 . . 119.0(2)
C41 C11 C21 . . 115.9(2)
C51 C11 C21 . . 117.8(2)
C41 C11 C31 . . 116.9(2)
C51 C11 C31 . . 114.9(2)
C21 C11 C31 . . 57.6(2)
C31 C21 C11 . . 61.6(2)
C31 C21 H21A . . 117.6
C11 C21 H21A . . 117.6
C31 C21 H21B . . 117.6
C11 C21 H21B . . 117.6
H21A C21 H21B . . 114.7
C21 C31 C11 . . 60.8(2)
C21 C31 H31A . . 117.7
C11 C31 H31A . . 117.7
C21 C31 H31B . . 117.7
C11 C31 H31B . . 117.7
H31A C31 H31B . . 114.8
O21 C41 O11 . . 122.1(2)
O21 C41 C11 . . 125.7(2)
O11 C41 C11 . . 112.2(2)
O41 C51 O31 . . 124.8(2)
O41 C51 C11 . . 124.1(2)
O31 C51 C11 . . 110.9(2)
C42 O22 H22 . . 109(4)
C52 O42 Na1 . . 142.02(19)
C42 C12 C52 . . 119.5(2)
C42 C12 C32 . . 116.4(2)
C52 C12 C32 . . 116.0(2)
C42 C12 C22 . . 116.4(2)
C52 C12 C22 . . 116.4(2)
C32 C12 C22 . . 57.1(2)
C32 C22 C12 . . 61.39(19)
C32 C22 H22A . . 117.6
C12 C22 H22A . . 117.6
C32 C22 H22B . . 117.6
C12 C22 H22B . . 117.6
H22A C22 H22B . . 114.7
C22 C32 C12 . . 61.5(2)
C22 C32 H32A . . 117.6
C12 C32 H32A . . 117.6
C22 C32 H32B . . 117.6
C12 C32 H32B . . 117.6
H32A C32 H32B . . 114.7
O12 C42 O22 . . 121.9(3)
O12 C42 C12 . . 121.9(3)
O22 C42 C12 . . 116.1(2)
O32 C52 O42 . . 124.4(3)
O32 C52 C12 . . 118.3(2)
O42 C52 C12 . . 117.2(2)
Na1 O1W H1W . . 99(2)
Na1 O1W H2W . . 129(3)
H1W O1W H2W . . 100(4)
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 O42 . 2.261(2) yes
Na1 O21 2_667 2.325(2) yes
Na1 O41 2_667 2.370(2) yes
Na1 O41 1_455 2.384(2) yes
Na1 O1W . 2.526(3) yes
Na1 O21 . 2.533(2) yes
Na1 Na1 2_567 3.245(2) yes
Na1 Na1 2_667 3.769(3) yes
O11 C41 . 1.320(3) yes
O11 H11 . 0.77(5) ?
O21 C41 . 1.204(3) yes
O21 Na1 2_667 2.325(2) ?
O31 C51 . 1.301(3) yes
O31 H31 . 0.72(6) ?
O41 C51 . 1.207(3) yes
O41 Na1 2_667 2.370(2) ?
O41 Na1 1_655 2.384(2) ?
C11 C41 . 1.491(3) ?
C11 C51 . 1.503(3) ?
C11 C21 . 1.513(4) yes
C11 C31 . 1.525(4) yes
C21 C31 . 1.464(5) yes
C21 H21A . 0.97 ?
C21 H21B . 0.97 ?
C31 H31A . 0.97 ?
C31 H31B . 0.97 ?
O12 C42 . 1.215(3) yes
O22 C42 . 1.298(4) yes
O22 H22 . 0.93(6) ?
O32 C52 . 1.233(3) yes
O42 C52 . 1.258(3) yes
C12 C42 . 1.491(4) ?
C12 C52 . 1.504(4) ?
C12 C32 . 1.518(4) yes
C12 C22 . 1.520(4) yes
C22 C32 . 1.451(5) yes
C22 H22A . 0.97 ?
C22 H22B . 0.97 ?
C32 H32A . 0.97 ?
C32 H32B . 0.97 ?
O1W H1W . 0.85(4) ?
O1W H2W . 0.86(4) ?
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 H22 O42 . 0.93(6) 1.56(6) 2.429(3) 154(5)
O1W H2W O12 2_657 0.86(4) 1.90(4) 2.737(3) 162(4)
O1W H1W O22 1_455 0.85(4) 1.98(4) 2.777(4) 155(3)
O11 H11 O1W 2_567 0.77(5) 1.88(5) 2.642(3) 170(5)
O31 H31 O32 1_655 0.72(6) 1.80(6) 2.478(3) 155(6)
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
_geom_torsion_publ_flag
O42 Na1 O21 C41 . . 49.41(19) ?
O21 Na1 O21 C41 2_667 . 137.8(2) ?
O41 Na1 O21 C41 2_667 . -146.76(18) ?
O41 Na1 O21 C41 1_455 . -51.28(18) ?
O1W Na1 O21 C41 . . 167.4(3) ?
Na1 Na1 O21 C41 2_567 . -99.11(18) ?
Na1 Na1 O21 C41 2_667 . 137.8(2) ?
O42 Na1 O21 Na1 . 2_667 -88.41(9) ?
O41 Na1 O21 Na1 2_667 2_667 75.43(8) ?
O41 Na1 O21 Na1 1_455 2_667 170.91(9) ?
O1W Na1 O21 Na1 . 2_667 29.6(3) ?
Na1 Na1 O21 Na1 2_567 2_667 123.07(8) ?
C41 C11 C21 C31 . . 106.7(3) ?
C51 C11 C21 C31 . . -103.3(3) ?
C41 C11 C31 C21 . . -105.0(3) ?
C51 C11 C31 C21 . . 108.4(3) ?
Na1 O21 C41 O11 2_667 . -135.2(2) ?
Na1 O21 C41 O11 . . 96.4(3) ?
Na1 O21 C41 C11 2_667 . 47.5(3) ?
Na1 O21 C41 C11 . . -80.9(3) ?
C51 C11 C41 O21 . . -1.4(4) yes
C21 C11 C41 O21 . . 148.3(3) ?
C31 C11 C41 O21 . . -146.7(3) ?
C51 C11 C41 O11 . . -178.9(2) ?
C21 C11 C41 O11 . . -29.3(3) ?
C31 C11 C41 O11 . . 35.8(3) ?
Na1 O41 C51 O31 2_667 . 173.4(2) ?
Na1 O41 C51 O31 1_655 . 6.5(5) ?
Na1 O41 C51 C11 2_667 . -3.1(4) ?
Na1 O41 C51 C11 1_655 . -170.0(2) ?
C41 C11 C51 O41 . . -23.0(4) yes
C21 C11 C51 O41 . . -172.1(3) ?
C31 C11 C51 O41 . . 122.9(3) ?
C41 C11 C51 O31 . . 160.1(2) ?
C21 C11 C51 O31 . . 11.0(4) ?
C31 C11 C51 O31 . . -54.0(3) ?
O21 Na1 O42 C52 2_667 . -167.9(4) ?
O41 Na1 O42 C52 2_667 . -170.7(3) ?
O41 Na1 O42 C52 1_455 . -9.6(4) ?
O1W Na1 O42 C52 . . 102.9(4) ?
O21 Na1 O42 C52 . . -89.7(4) ?
Na1 Na1 O42 C52 2_567 . -16.7(5) ?
Na1 Na1 O42 C52 2_667 . -126.9(4) ?
C42 C12 C22 C32 . . 105.6(3) ?
C52 C12 C22 C32 . . -105.2(3) ?
C42 C12 C32 C22 . . -105.7(3) ?
C52 C12 C32 C22 . . 105.8(3) ?
C52 C12 C42 O12 . . 177.4(3) ?
C32 C12 C42 O12 . . 30.1(4) ?
C22 C12 C42 O12 . . -34.4(4) ?
C52 C12 C42 O22 . . -3.1(4) yes
C32 C12 C42 O22 . . -150.4(3) ?
C22 C12 C42 O22 . . 145.1(3) ?
Na1 O42 C52 O32 . . 11.3(6) ?
Na1 O42 C52 C12 . . -170.4(2) ?
C42 C12 C52 O32 . . -179.7(3) ?
C32 C12 C52 O32 . . -32.3(4) ?
C22 C12 C52 O32 . . 32.0(4) ?
C42 C12 C52 O42 . . 1.9(4) yes
C32 C12 C52 O42 . . 149.3(3) ?
C22 C12 C52 O42 . . -146.4(3) ?
