#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/31/2223196.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_2223196
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
_publ_section_title
;
 Sodium 2-nitrocinnamate dihydrate: a one-dimensional hydrogen-bonded
 coordination polymer
;
_journal_coeditor_code           SU2131
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1048
_journal_paper_doi               10.1107/S1600536809030402
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Na (C9 H6 N O4) (H2 O)2]'
_chemical_formula_moiety         'C9 H10 N Na O6'
_chemical_formula_sum            'C9 H10 N Na O6'
_chemical_formula_weight         251.17
_chemical_name_common
'sodium trans-2-nitrocinnamate dihydrate'
_chemical_name_systematic
;
catena-poly[aquasodium-μ₂-aqua-μ₃-2-nitrocinnamato]
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.239(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.4179(7)
_cell_length_b                   3.6899(2)
_cell_length_c                   14.8738(7)
_cell_measurement_reflns_used    2943
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.73
_cell_measurement_theta_min      2.96
_cell_volume                     1064.90(9)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution
'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-S CCD-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6531
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.186
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0708P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                1626
_reflns_number_total             2100
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2131.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223196
_cod_database_fobs_code          2223196
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Na Na1 0.05494(3) 0.73072(17) -0.06704(4) 0.0272(2) Uani . . 1.000
O O1W 0.02635(6) 0.2374(3) -0.16440(8) 0.0319(4) Uani . . 1.000
O O2W 0.16105(8) 0.6812(5) -0.14886(12) 0.0691(7) Uani . . 1.000
O O21 0.29871(7) 0.4625(6) 0.31366(9) 0.0637(6) Uani . . 1.000
O O22 0.39979(7) 0.2280(5) 0.32066(10) 0.0541(6) Uani . . 1.000
O O31 0.06940(6) 0.2430(3) 0.04255(8) 0.0282(4) Uani . . 1.000
O O32 0.10417(6) 0.0743(4) 0.18086(8) 0.0336(4) Uani . . 1.000
N N21 0.35246(7) 0.3769(4) 0.27927(10) 0.0339(5) Uani . . 1.000
C C1 0.30837(8) 0.4562(5) 0.12070(11) 0.0267(5) Uani . . 1.000
C C2 0.36252(8) 0.4742(4) 0.18535(11) 0.0261(5) Uani . . 1.000
C C3 0.42813(9) 0.5880(5) 0.16617(12) 0.0327(6) Uani . . 1.000
C C4 0.44154(10) 0.6987(5) 0.08063(14) 0.0384(6) Uani . . 1.000
C C5 0.38972(10) 0.6860(5) 0.01494(13) 0.0368(6) Uani . . 1.000
C C6 0.32514(9) 0.5634(5) 0.03431(12) 0.0346(6) Uani . . 1.000
C C11 0.23935(9) 0.3141(5) 0.13955(12) 0.0297(5) Uani . . 1.000
C C21 0.18383(9) 0.3638(5) 0.08772(13) 0.0345(6) Uani . . 1.000
C C31 0.11421(8) 0.2155(4) 0.10637(11) 0.0256(5) Uani . . 1.000
H H3 0.46290 0.58950 0.21090 0.0390 Uiso calc R 1.000
H H4 0.48520 0.78150 0.06720 0.0460 Uiso calc R 1.000
H H5 0.39850 0.76120 -0.04320 0.0440 Uiso calc R 1.000
H H6 0.29140 0.55150 -0.01180 0.0420 Uiso calc R 1.000
H H11 0.23490 0.17970 0.19190 0.0360 Uiso calc R 1.000
H H11W 0.0460(11) 0.241(6) -0.209(2) 0.055(8) Uiso . . 1.000
H H12W -0.0168(12) 0.157(7) -0.1733(17) 0.044(8) Uiso . . 1.000
H H21 0.18810 0.50100 0.03580 0.0410 Uiso calc R 1.000
H H21W 0.1828(16) 0.851(9) -0.138(2) 0.093(13) Uiso . . 1.000
H H22W 0.1500(18) 0.666(12) -0.209(2) 0.101(14) Uiso . . 1.000
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'
N N 0.0061 0.0033 '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'
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1W Na1 O2W . . . 79.67(5) no
O1W Na1 O31 . . . 81.96(4) no
O1W Na1 O1W . . 1_565 100.64(4) no
O1W Na1 O31 . . 1_565 172.53(5) no
O1W Na1 O31 . . 3_565 85.02(4) no
O2W Na1 O31 . . . 101.58(6) no
O1W Na1 O2W 1_565 . . 86.43(5) no
O2W Na1 O31 . . 1_565 107.80(5) no
O2W Na1 O31 . . 3_565 158.48(6) no
O1W Na1 O31 1_565 . . 171.93(5) no
O31 Na1 O31 . . 1_565 96.60(4) no
O31 Na1 O31 . . 3_565 91.04(4) no
O1W Na1 O31 1_565 . 1_565 79.83(4) no
O1W Na1 O31 1_565 . 3_565 81.62(4) no
O31 Na1 O31 1_565 . 3_565 87.68(4) no
Na1 O1W Na1 . . 1_545 100.64(5) no
Na1 O31 C31 . . . 128.20(10) no
Na1 O31 Na1 . . 1_545 96.60(5) no
Na1 O31 Na1 . . 3_565 88.96(4) no
Na1 O31 C31 1_545 . . 118.92(10) no
Na1 O31 C31 3_565 . . 122.84(10) no
Na1 O31 Na1 1_545 . 3_565 92.32(4) no
H11W O1W H12W . . . 112(2) no
H21W O2W H22W . . . 111(4) no
O21 N21 C2 . . . 118.98(14) no
O22 N21 C2 . . . 117.87(14) no
O21 N21 O22 . . . 123.06(16) no
C2 C1 C6 . . . 115.06(15) no
C2 C1 C11 . . . 123.37(15) no
C6 C1 C11 . . . 121.46(15) no
N21 C2 C1 . . . 121.34(14) no
N21 C2 C3 . . . 115.49(14) no
C1 C2 C3 . . . 123.16(15) no
C2 C3 C4 . . . 119.49(17) no
C3 C4 C5 . . . 119.26(18) no
C4 C5 C6 . . . 120.69(18) no
C1 C6 C5 . . . 122.29(16) no
C1 C11 C21 . . . 124.71(17) no
C11 C21 C31 . . . 124.59(17) no
O31 C31 C21 . . . 115.57(14) no
O32 C31 C21 . . . 119.48(15) no
O31 C31 O32 . . . 124.96(15) no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C1 C6 H6 . . . 119.00 no
C5 C6 H6 . . . 119.00 no
C1 C11 H11 . . . 118.00 no
C21 C11 H11 . . . 118.00 no
C11 C21 H21 . . . 118.00 no
C31 C21 H21 . . . 118.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Na1 O1W . . 2.3782(13) no
Na1 O2W . . 2.4404(17) no
Na1 O31 . . 2.4370(13) no
Na1 O1W . 1_565 2.4162(13) no
Na1 O31 . 1_565 2.5046(13) no
Na1 O31 . 3_565 2.4577(13) no
O21 N21 . . 1.222(2) no
O22 N21 . . 1.217(2) no
O31 C31 . . 1.267(2) no
O32 C31 . . 1.247(2) no
O1W H11W . . 0.78(3) no
O1W H12W . . 0.89(2) no
O2W H21W . . 0.77(3) no
O2W H22W . . 0.91(4) no
N21 C2 . . 1.463(2) no
C1 C2 . . 1.399(2) no
C1 C6 . . 1.395(2) no
C1 C11 . . 1.476(2) no
C2 C3 . . 1.382(2) no
C3 C4 . . 1.371(3) no
C4 C5 . . 1.376(3) no
C5 C6 . . 1.374(3) no
C11 C21 . . 1.314(3) no
C21 C31 . . 1.494(2) no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C11 H11 . . 0.9300 no
C21 H21 . . 0.9300 no
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
_geom_hbond_publ_flag
O1W H11W O32 4_554 0.78(3) 2.14(3) 2.8871(17) 162(2) yes
O1W H12W O32 3_555 0.89(2) 1.90(2) 2.7852(17) 171(2) yes
O2W H21W O21 4_564 0.77(3) 2.49(3) 3.050(2) 131(3) yes
O2W H22W O32 4_554 0.91(4) 2.04(5) 2.882(2) 153(4) yes
C11 H11 O21 . 0.93 2.39 2.846(2) 110 no
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2W Na1 O1W Na1 . . . 1_545 95.66(6) no
O31 Na1 O1W Na1 . . . 1_545 -7.75(5) no
O1W Na1 O1W Na1 1_565 . . 1_545 180.00(6) no
O31 Na1 O1W Na1 3_565 . . 1_545 -99.51(5) no
O1W Na1 O31 C31 . . . . 142.67(13) no
O1W Na1 O31 Na1 . . . 1_545 7.39(4) no
O1W Na1 O31 Na1 . . . 3_565 -84.82(4) no
O2W Na1 O31 C31 . . . . 65.02(14) no
O2W Na1 O31 Na1 . . . 1_545 -70.26(6) no
O2W Na1 O31 Na1 . . . 3_565 -162.47(5) no
O31 Na1 O31 C31 1_565 . . . -44.72(13) no
O31 Na1 O31 Na1 1_565 . . 1_545 180.00(4) no
O31 Na1 O31 Na1 1_565 . . 3_565 87.79(4) no
O31 Na1 O31 C31 3_565 . . . -132.51(13) no
O31 Na1 O31 Na1 3_565 . . 1_545 92.21(5) no
O31 Na1 O31 Na1 3_565 . . 3_565 0.00(3) no
O1W Na1 O1W Na1 . . 1_565 1_565 -180.00(6) no
O2W Na1 O1W Na1 . . 1_565 1_565 -101.22(6) no
O2W Na1 O31 Na1 . . 1_565 1_565 75.56(6) no
O2W Na1 O31 C31 . . 1_565 1_565 -65.26(12) no
O31 Na1 O31 Na1 . . 1_565 1_565 180.00(3) no
O31 Na1 O31 C31 . . 1_565 1_565 39.19(12) no
O1W Na1 O31 Na1 . . 3_565 3_565 81.83(4) no
O1W Na1 O31 C31 . . 3_565 3_565 -54.58(11) no
O2W Na1 O31 Na1 . . 3_565 3_565 126.42(15) no
O2W Na1 O31 C31 . . 3_565 3_565 -10.0(2) no
O31 Na1 O31 Na1 . . 3_565 3_565 0.00(5) no
O31 Na1 O31 C31 . . 3_565 3_565 -136.41(11) no
Na1 O31 C31 O32 . . . . 145.52(13) no
Na1 O31 C31 C21 . . . . -35.11(19) no
Na1 O31 C31 O32 1_545 . . . -87.48(18) no
Na1 O31 C31 C21 1_545 . . . 91.89(14) no
Na1 O31 C31 O32 3_565 . . . 26.8(2) no
Na1 O31 C31 C21 3_565 . . . -153.81(11) no
O21 N21 C2 C1 . . . . -38.6(2) no
O21 N21 C2 C3 . . . . 140.47(18) no
O22 N21 C2 C1 . . . . 144.65(17) no
O22 N21 C2 C3 . . . . -36.2(2) no
C6 C1 C2 N21 . . . . 178.85(15) no
C6 C1 C2 C3 . . . . -0.2(3) no
C11 C1 C2 N21 . . . . -4.8(3) no
C11 C1 C2 C3 . . . . 176.18(17) no
C2 C1 C6 C5 . . . . -1.5(3) no
C11 C1 C6 C5 . . . . -177.99(17) no
C2 C1 C11 C21 . . . . 164.51(18) no
C6 C1 C11 C21 . . . . -19.4(3) no
N21 C2 C3 C4 . . . . -177.36(16) no
C1 C2 C3 C4 . . . . 1.7(3) no
C2 C3 C4 C5 . . . . -1.6(3) no
C3 C4 C5 C6 . . . . -0.1(3) no
C4 C5 C6 C1 . . . . 1.7(3) no
C1 C11 C21 C31 . . . . 179.16(16) no
C11 C21 C31 O31 . . . . -169.51(17) no
C11 C21 C31 O32 . . . . 9.9(3) no
