#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/56/2225683.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_2225683
loop_
_publ_author_name
'Danish, Muhammad'
'Saleem, Iram'
'Ahmad, Nazir'
'Raza, Abdul Rauf'
'Starosta, Wojciech'
'Leciejewicz, Janusz'
_publ_section_title
;
 catena-Poly[[(2-methylbenzoato-κ²O,O')sodium]-di-μ-aqua-κ⁴O:O']
;
_journal_coeditor_code           WM2315
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m459
_journal_page_last               m460
_journal_paper_doi               10.1107/S1600536810010536
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Na (C8 H7 O2) (H2 O)2]'
_chemical_formula_moiety         'C8 H11 Na O4'
_chemical_formula_sum            'C8 H11 Na O4'
_chemical_formula_weight         194.16
_chemical_name_common            'Sodium ortho-toluate dihydrate'
_chemical_name_systematic
;
catena-Poly[[(2-methylbenzoato-κ²O,O')sodium]-
di-μ-aqua-κ⁴O:O']
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.98(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.145(3)
_cell_length_b                   8.1155(16)
_cell_length_c                   7.3986(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      6
_cell_volume                     968.1(3)
_computing_cell_refinement       'KM-4 Software (Kuma, 1996)'
_computing_data_collection       'KM-4 Software (Kuma, 1996)'
_computing_data_reduction        'DATAPROC (Kuma, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Kuma KM-4 four-circle diffractometer'
_diffrn_measurement_method       'profile data from ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3057
_diffrn_reflns_theta_full        30.05
_diffrn_reflns_theta_max         30.05
_diffrn_reflns_theta_min         1.26
_diffrn_standards_decay_%        0.77
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9522
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.548
_exptl_crystal_size_mid          0.414
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0889P)²+0.1369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                1919
_reflns_number_total             2845
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wm2315.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225683
_cod_database_fobs_code          2225683
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
Na Na1 0.01791(3) 0.64831(7) 0.25611(7) 0.03320(17) Uani d . 1 . .
O O2 0.14852(7) 0.53347(14) 0.41532(13) 0.0386(2) Uani d . 1 . .
C C7 0.18004(8) 0.53264(15) 0.26404(16) 0.0273(2) Uani d . 1 . .
C C1 0.27247(8) 0.53757(16) 0.25234(17) 0.0305(3) Uani d . 1 . .
C C2 0.32656(10) 0.4527(2) 0.3718(2) 0.0425(3) Uani d . 1 . .
C C6 0.30354(11) 0.6271(3) 0.1107(2) 0.0492(4) Uani d . 1 . .
C C3 0.41092(11) 0.4583(3) 0.3414(3) 0.0562(5) Uani d . 1 . .
C C8 0.29779(16) 0.3518(4) 0.5275(4) 0.0852(9) Uani d . 1 . .
H H8A 0.2774 0.4239 0.6181 0.128 Uiso calc R 1 . .
H H8B 0.3434 0.2884 0.5788 0.128 Uiso calc R 1 . .
H H8C 0.2542 0.2789 0.4848 0.128 Uiso calc R 1 . .
C C5 0.38805(13) 0.6352(3) 0.0885(4) 0.0694(6) Uani d . 1 . .
C C4 0.44096(12) 0.5494(3) 0.2038(4) 0.0672(6) Uani d . 1 . .
O O1 0.13648(6) 0.53062(13) 0.11780(13) 0.0367(2) Uani d . 1 . .
O O3 0.08470(7) 0.91596(13) 0.25956(15) 0.0365(2) Uani d . 1 . .
O O4 -0.05771(7) 0.74541(15) 0.49901(14) 0.0357(2) Uani d . 1 . .
H H32 0.1128(15) 0.918(3) 0.179(4) 0.055(6) Uiso d . 1 . .
H H31 0.1175(16) 0.921(3) 0.357(4) 0.069(7) Uiso d . 1 . .
H H41 -0.0863(15) 0.676(3) 0.526(3) 0.057(7) Uiso d . 1 . .
H H42 -0.0901(14) 0.819(3) 0.458(3) 0.056(6) Uiso d . 1 . .
H H5 0.2640(13) 0.693(3) 0.026(3) 0.056(6) Uiso d . 1 . .
H H2 0.4464(15) 0.395(3) 0.412(3) 0.060(6) Uiso d . 1 . .
H H4 0.4058(17) 0.705(4) -0.018(4) 0.092(9) Uiso d . 1 . .
H H3 0.495(2) 0.556(4) 0.179(4) 0.096(9) Uiso d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O4 Na1 O4 . 4_575 102.97(4) ?
O4 Na1 O1 . . 155.22(5) ?
O4 Na1 O1 4_575 . 100.99(4) ?
O4 Na1 O3 . . 86.57(5) ?
O4 Na1 O3 4_575 . 83.84(5) ?
O1 Na1 O3 . . 89.82(4) ?
O4 Na1 O3 . 2_545 85.39(5) ?
O4 Na1 O3 4_575 2_545 85.70(5) ?
O1 Na1 O3 . 2_545 102.67(4) ?
O3 Na1 O3 . 2_545 165.05(4) ?
O4 Na1 O2 . . 102.67(5) ?
O4 Na1 O2 4_575 . 152.54(4) ?
O1 Na1 O2 . . 52.67(4) ?
O3 Na1 O2 . . 88.04(4) ?
O3 Na1 O2 2_545 . 106.03(4) ?
O4 Na1 C7 . . 128.38(5) ?
O4 Na1 C7 4_575 . 125.85(5) ?
O1 Na1 C7 . . 26.92(4) ?
O3 Na1 C7 . . 83.36(4) ?
O3 Na1 C7 2_545 . 111.48(4) ?
O2 Na1 C7 . . 26.78(3) ?
O4 Na1 Na1 . 4_575 125.73(4) ?
O4 Na1 Na1 4_575 4_575 30.99(3) ?
O1 Na1 Na1 . 4_575 74.72(3) ?
O3 Na1 Na1 . 4_575 67.88(3) ?
O3 Na1 Na1 2_545 4_575 107.18(3) ?
O2 Na1 Na1 . 4_575 122.27(3) ?
C7 Na1 Na1 . 4_575 96.45(4) ?
O4 Na1 Na1 . 4_576 31.13(3) ?
O4 Na1 Na1 4_575 4_576 124.09(4) ?
O1 Na1 Na1 . 4_576 125.87(3) ?
O3 Na1 Na1 . 4_576 69.30(4) ?
O3 Na1 Na1 2_545 4_576 108.49(3) ?
O2 Na1 Na1 . 4_576 76.42(3) ?
C7 Na1 Na1 . 4_576 99.38(4) ?
Na1 Na1 Na1 4_575 4_576 131.91(3) ?
O4 Na1 Na1 . 2_545 105.63(4) ?
O4 Na1 Na1 4_575 2_545 106.05(4) ?
O1 Na1 Na1 . 2_545 73.32(3) ?
O3 Na1 Na1 . 2_545 161.66(4) ?
O3 Na1 Na1 2_545 2_545 33.16(3) ?
O2 Na1 Na1 . 2_545 76.09(3) ?
C7 Na1 Na1 . 2_545 78.33(3) ?
Na1 Na1 Na1 4_575 2_545 112.95(2) ?
Na1 Na1 Na1 4_576 2_545 114.63(2) ?
O4 Na1 Na1 . 2 66.94(3) ?
O4 Na1 Na1 4_575 2 63.62(3) ?
O1 Na1 Na1 . 2 119.76(4) ?
O3 Na1 Na1 . 2 34.47(3) ?
O3 Na1 Na1 2_545 2 130.62(4) ?
O2 Na1 Na1 . 2 119.11(3) ?
C7 Na1 Na1 . 2 117.81(3) ?
Na1 Na1 Na1 4_575 2 65.37(2) ?
Na1 Na1 Na1 4_576 2 67.05(2) ?
Na1 Na1 Na1 2_545 2 163.72(3) ?
C7 O2 Na1 . . 87.34(8) ?
O2 C7 O1 . . 122.18(12) ?
O2 C7 C1 . . 120.18(11) ?
O1 C7 C1 . . 117.62(12) ?
O2 C7 Na1 . . 65.88(8) ?
O1 C7 Na1 . . 60.19(7) ?
C1 C7 Na1 . . 158.26(9) ?
C6 C1 C2 . . 119.88(15) ?
C6 C1 C7 . . 117.16(13) ?
C2 C1 C7 . . 122.92(13) ?
C1 C2 C3 . . 117.90(16) ?
C1 C2 C8 . . 123.11(16) ?
C3 C2 C8 . . 118.97(17) ?
C5 C6 C1 . . 120.70(18) ?
C5 C6 H5 . . 119.4(12) ?
C1 C6 H5 . . 119.8(12) ?
C4 C3 C2 . . 121.71(18) ?
C4 C3 H2 . . 119.7(15) ?
C2 C3 H2 . . 118.5(15) ?
C2 C8 H8A . . 109.5 ?
C2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C4 C5 C6 . . 119.3(2) ?
C4 C5 H4 . . 124.9(16) ?
C6 C5 H4 . . 115.8(16) ?
C5 C4 C3 . . 120.39(17) ?
C5 C4 H3 . . 115(2) ?
C3 C4 H3 . . 125(2) ?
C7 O1 Na1 . . 92.89(8) ?
Na1 O3 Na1 . 2 112.37(5) ?
Na1 O3 H32 . . 107.0(18) ?
Na1 O3 H32 2 . 111.3(18) ?
Na1 O3 H31 . . 107.4(17) ?
Na1 O3 H31 2 . 111.9(17) ?
H32 O3 H31 . . 106(2) ?
Na1 O4 Na1 . 4_576 117.88(5) ?
Na1 O4 H41 . . 107.1(18) ?
Na1 O4 H41 4_576 . 110.8(17) ?
Na1 O4 H42 . . 107.3(15) ?
Na1 O4 H42 4_576 . 108.5(16) ?
H41 O4 H42 . . 104(2) ?
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 O4 . 2.3599(13) y
Na1 O4 4_575 2.3689(13) y
Na1 O1 . 2.4141(13) y
Na1 O3 . 2.4245(13) y
Na1 O3 2_545 2.5086(13) y
Na1 O2 . 2.5387(14) y
Na1 C7 . 2.7787(14) ?
Na1 Na1 4_575 4.0508(8) ?
Na1 Na1 4_576 4.0508(8) ?
Na1 Na1 2_545 4.0990(8) ?
Na1 Na1 2 4.0991(8) ?
O2 C7 . 1.2534(16) ?
C7 O1 . 1.2596(16) ?
C7 C1 . 1.4999(18) ?
C1 C6 . 1.390(2) ?
C1 C2 . 1.392(2) ?
C2 C3 . 1.393(3) ?
C2 C8 . 1.506(3) ?
C6 C5 . 1.384(3) ?
C6 H5 . 1.02(2) ?
C3 C4 . 1.367(4) ?
C3 H2 . 0.91(3) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C5 C4 . 1.366(4) ?
C5 H4 . 1.02(3) ?
C4 H3 . 0.90(3) ?
O3 Na1 2 2.5087(13) ?
O3 H32 . 0.77(3) ?
O3 H31 . 0.88(3) ?
O4 Na1 4_576 2.3689(13) ?
O4 H41 . 0.76(3) ?
O4 H42 . 0.84(3) ?
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
O4 H42 O1 2 0.84(3) 1.94(3) 2.7582(17) 163(2)
O4 H41 O2 3_566 0.76(3) 2.03(3) 2.7874(17) 171(2)
O3 H31 O1 4_576 0.88(3) 1.97(3) 2.7716(16) 151(2)
O3 H32 O2 4_575 0.77(3) 2.10(3) 2.8265(16) 158(2)
