#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/49/2234909.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_2234909
loop_
_publ_author_name
'Bouchameni, Chahra'
'Beghidja, Chahrazed'
'Beghidja, Adel'
'Boutebdja, Mehdi'
_publ_section_title
;
 Aquabis[N'-(1,3-dithiolan-2-ylidene)-2-hydroxybenzohydrazidato(0.5{-})-κ²N',O]sodium(I)
;
_journal_coeditor_code           BQ2359
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m827
_journal_page_last               m828
_journal_paper_doi               10.1107/S1600536812023239
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Na (C10 H9.5 N2 O2 S2)2 (H2 O1)]'
_chemical_formula_moiety         'C20 H21 N4 Na O5 S4'
_chemical_formula_sum            'C20 H21 N4 Na O5 S4'
_chemical_formula_weight         548.68
_chemical_name_systematic
;
Aquabis[N'-(1,3-dithiolan-2-ylidene)-2-hydroxybenzohydrazidato(0.5-)-
κ²N',O]sodium(I)
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 117.804(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.6960(16)
_cell_length_b                   5.9330(3)
_cell_length_c                   13.5240(12)
_cell_measurement_reflns_used    2559
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1184.99(17)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3660
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.70
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.460
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.426
_refine_ls_abs_structure_details 'Flack (1983), 970 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.06(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2463
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0458P)²+2.9944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1262
_reflns_number_gt                2083
_reflns_number_total             2463
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bq2359.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2234909
_cod_database_fobs_code          2234909
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,-z
3 1/2+x,1/2+y,z
4 1/2-x,1/2+y,-z
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
S S1 0.34168(7) 0.79324(19) 0.76027(8) 0.0330(3) Uani . . 1.000
S S2 0.33261(8) 1.0904(2) 0.57897(10) 0.0388(4) Uani . . 1.000
Na Na1 0.50000 0.7068(4) 0.50000 0.0324(8) Uani . . 1.000
O O1 0.5618(2) 0.4475(5) 0.6448(2) 0.0318(9) Uani . . 1.000
O O2 0.5000(2) 0.3636(5) 0.9088(2) 0.0348(10) Uani . . 1.000
O O3 0.50000 1.0799(9) 0.50000 0.057(2) Uani . . 1.000
N N1 0.4834(2) 0.5736(6) 0.7318(2) 0.0245(10) Uani . . 1.000
N N2 0.4434(2) 0.7412(6) 0.6540(3) 0.0261(10) Uani . . 1.000
C C1 0.5421(3) 0.4301(7) 0.7235(3) 0.0261(12) Uani . . 1.000
C C2 0.5809(3) 0.2538(7) 0.8092(3) 0.0249(11) Uani . . 1.000
C C3 0.5575(3) 0.2237(7) 0.8968(3) 0.0282(11) Uani . . 1.000
C C4 0.5962(3) 0.0414(8) 0.9695(4) 0.0393(16) Uani . . 1.000
C C5 0.6562(3) -0.1025(9) 0.9594(4) 0.0400(16) Uani . . 1.000
C C6 0.6809(3) -0.0701(8) 0.8755(4) 0.0373(14) Uani . . 1.000
C C7 0.6425(3) 0.1041(8) 0.8012(3) 0.0325(12) Uani . . 1.000
C C8 0.3821(3) 0.8554(7) 0.6639(3) 0.0262(11) Uani . . 1.000
C C9 0.2806(3) 1.0562(9) 0.7390(4) 0.0400(16) Uani . . 1.000
C C10 0.2425(3) 1.1176(9) 0.6176(4) 0.0453(16) Uani . . 1.000
H H1 0.47040 0.56020 0.78750 0.0290 Uiso calc . 1.000
H H2 0.512(8) 0.379(19) 0.980(3) 0.0680 Uiso . . 0.500
H H3 0.470(4) 1.171(8) 0.435(3) 0.0680 Uiso . . 1.000
H H4 0.58030 0.01670 1.02760 0.0470 Uiso calc R 1.000
H H5 0.68110 -0.22480 1.01000 0.0480 Uiso calc R 1.000
H H6 0.72380 -0.16700 0.86960 0.0450 Uiso calc R 1.000
H H7 0.65820 0.12360 0.74260 0.0390 Uiso calc R 1.000
H H9A 0.23110 1.03850 0.75920 0.0480 Uiso calc R 1.000
H H9B 0.32190 1.17610 0.78640 0.0480 Uiso calc R 1.000
H H10A 0.21950 1.27430 0.60530 0.0540 Uiso calc R 1.000
H H10B 0.19180 1.01580 0.57130 0.0540 Uiso calc R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 '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
C8 S1 C9 . . 94.8(2) no
C8 S2 C10 . . 94.8(2) no
O1 Na1 O3 . . 131.54(8) no
O1 Na1 N2 . . 64.63(11) no
O1 Na1 O1 . 2_656 96.91(13) no
O1 Na1 N2 . 2_656 122.01(13) no
O3 Na1 N2 . . 85.61(9) no
O1 Na1 O3 2_656 . 131.54(8) no
O3 Na1 N2 . 2_656 85.61(9) no
O1 Na1 N2 2_656 . 122.01(13) no
N2 Na1 N2 . 2_656 171.22(15) no
O1 Na1 N2 2_656 2_656 64.63(11) no
Na1 O1 C1 . . 125.5(3) no
C3 O2 H2 . . 113(8) no
Na1 O3 H3 . . 125(3) no
Na1 O3 H3 . 2_656 125(3) no
H3 O3 H3 . 2_656 111(4) no
N2 N1 C1 . . 120.6(3) no
Na1 N2 N1 . . 108.7(2) no
Na1 N2 C8 . . 135.3(3) no
N1 N2 C8 . . 115.4(4) no
C1 N1 H1 . . 120.00 no
N2 N1 H1 . . 120.00 no
N1 C1 C2 . . 117.2(4) no
O1 C1 N1 . . 120.6(4) no
O1 C1 C2 . . 122.3(4) no
C1 C2 C7 . . 117.4(4) no
C3 C2 C7 . . 118.8(4) no
C1 C2 C3 . . 123.8(4) no
C2 C3 C4 . . 117.8(4) no
O2 C3 C2 . . 121.1(4) no
O2 C3 C4 . . 121.2(4) no
C3 C4 C5 . . 122.0(5) no
C4 C5 C6 . . 120.3(5) no
C5 C6 C7 . . 119.1(5) no
C2 C7 C6 . . 122.0(4) no
S1 C8 S2 . . 115.2(3) no
S1 C8 N2 . . 124.4(3) no
S2 C8 N2 . . 120.5(3) no
S1 C9 C10 . . 107.6(4) no
S2 C10 C9 . . 107.9(4) no
C3 C4 H4 . . 119.00 no
C5 C4 H4 . . 119.00 no
C4 C5 H5 . . 120.00 no
C6 C5 H5 . . 120.00 no
C5 C6 H6 . . 120.00 no
C7 C6 H6 . . 120.00 no
C2 C7 H7 . . 119.00 no
C6 C7 H7 . . 119.00 no
S1 C9 H9A . . 110.00 no
S1 C9 H9B . . 110.00 no
C10 C9 H9A . . 110.00 no
C10 C9 H9B . . 110.00 no
H9A C9 H9B . . 108.00 no
S2 C10 H10A . . 110.00 no
S2 C10 H10B . . 110.00 no
C9 C10 H10A . . 110.00 no
C9 C10 H10B . . 110.00 no
H10A C10 H10B . . 108.00 no
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
S1 C8 . 1.764(5) no
S1 C9 . 1.812(6) no
S2 C8 . 1.750(4) no
S2 C10 . 1.815(6) no
Na1 O1 . 2.320(3) yes
Na1 O3 . 2.214(6) yes
Na1 N2 . 2.666(4) yes
Na1 O1 2_656 2.320(3) no
Na1 N2 2_656 2.666(4) no
O1 C1 . 1.256(5) no
O2 C3 . 1.335(6) no
O2 H2 . 0.89(5) no
O3 H3 2_656 0.95(4) no
O3 H3 . 0.95(4) no
N1 N2 . 1.373(5) no
N1 C1 . 1.342(6) no
N2 C8 . 1.285(6) no
N1 H1 . 0.8800 no
C1 C2 . 1.469(6) no
C2 C3 . 1.421(6) no
C2 C7 . 1.401(7) no
C3 C4 . 1.401(6) no
C4 C5 . 1.371(8) no
C5 C6 . 1.390(7) no
C6 C7 . 1.374(6) no
C9 C10 . 1.503(7) no
C4 H4 . 0.9500 no
C5 H5 . 0.9500 no
C6 H6 . 0.9500 no
C7 H7 . 0.9500 no
C9 H9A . 0.9900 no
C9 H9B . 0.9900 no
C10 H10A . 0.9900 no
C10 H10B . 0.9900 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 N1 2.880(4) . no
S1 C4 3.614(5) 2_667 no
S2 C10 3.660(5) 4_546 no
S2 O3 3.4263(15) . no
S1 H1 2.4300 . no
S1 H7 3.1300 3_455 no
S1 H4 2.8600 2_667 no
S2 H10A 2.9100 4_546 no
S2 H10B 3.1500 4_556 no
Na1 C10 3.633(6) 3_545 no
Na1 C10 3.633(6) 4_546 no
Na1 H10B 3.1000 3_545 no
Na1 H10B 3.1000 4_546 no
O1 O3 2.788(5) 1_545 no
O1 N2 2.681(5) . no
O1 C9 3.323(7) 3_545 no
O1 O3 2.788(5) 2_646 no
O1 C10 3.360(7) 3_545 no
O2 C4 3.378(6) 2_657 no
O2 N1 2.596(4) . no
O2 C3 3.298(5) 2_657 no
O2 O2 2.467(4) 2_657 no
O3 O1 2.788(5) 1_565 no
O3 S2 3.4263(15) 2_656 no
O3 O1 2.788(5) 2_666 no
O3 S2 3.4263(15) . no
O1 H7 2.4600 . no
O1 H10B 2.8100 3_545 no
O1 H3 1.90(4) 2_646 no
O1 H9A 2.5700 3_545 no
O2 H2 1.61(8) 2_657 no
O2 H9B 2.8700 1_545 no
O2 H4 2.8000 2_657 no
O2 H1 1.8800 . no
N1 S1 2.880(4) . no
N1 O1 2.257(5) . no
N1 O2 2.596(4) . no
N2 O1 2.681(5) . no
C3 O2 3.298(5) 2_657 no
C4 O2 3.378(6) 2_657 no
C4 S1 3.614(5) 2_647 no
C4 C9 3.495(7) 2_647 no
C9 O1 3.323(7) 3_455 no
C9 C4 3.495(7) 2_667 no
C10 O1 3.360(7) 3_455 no
C10 Na1 3.633(6) 3_455 no
C10 Na1 3.633(6) 4_556 no
C10 S2 3.660(5) 4_556 no
C1 H9A 3.0300 3_545 no
C1 H3 2.57(4) 2_646 no
C2 H3 3.04(4) 2_646 no
C3 H1 2.5100 . no
C3 H2 2.60(11) 2_657 no
C4 H9B 3.0300 2_647 no
C4 H2 2.98(12) 2_657 no
C4 H4 2.9700 2_657 no
C6 H5 2.9300 4_657 no
C7 H5 3.0300 4_657 no
C7 H3 2.88(4) 2_646 no
C9 H6 2.8800 3_465 no
C9 H4 2.9300 2_667 no
H1 S1 2.4300 . no
H1 O2 1.8800 . no
H1 C3 2.5100 . no
H1 H2 2.5900 . no
H2 H1 2.5900 . no
H2 H4 2.3800 . no
H2 O2 1.61(9) 2_657 no
H2 C3 2.60(11) 2_657 no
H2 C4 2.98(12) 2_657 no
H3 O1 1.90(4) 2_666 no
H3 C1 2.57(4) 2_666 no
H3 C2 3.04(4) 2_666 no
H3 C7 2.88(4) 2_666 no
H3 H7 2.3700 2_666 no
H4 H2 2.3800 . no
H4 S1 2.8600 2_647 no
H4 O2 2.8000 2_657 no
H4 C4 2.9700 2_657 no
H4 C9 2.9300 2_647 no
H4 H4 2.4200 2_657 no
H4 H9B 2.4600 2_647 no
H5 C6 2.9300 4_647 no
H5 C7 3.0300 4_647 no
H6 C9 2.8800 3_535 no
H6 H9A 2.3400 3_535 no
H6 H9B 2.5600 3_535 no
H7 O1 2.4600 . no
H7 H3 2.3700 2_646 no
H7 S1 3.1300 3_545 no
H9A O1 2.5700 3_455 no
H9A C1 3.0300 3_455 no
H9A H6 2.3400 3_465 no
H9B O2 2.8700 1_565 no
H9B C4 3.0300 2_667 no
H9B H4 2.4600 2_667 no
H9B H6 2.5600 3_465 no
H10A S2 2.9100 4_556 no
H10B Na1 3.1000 3_455 no
H10B O1 2.8100 3_455 no
H10B S2 3.1500 4_546 no
H10B Na1 3.1000 4_556 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
N1 H1 S1 . 0.8800 2.4300 2.880(4) 112.00 no
N1 H1 O2 . 0.8800 1.8800 2.596(4) 137.00 yes
O2 H2 O2 2_657 0.89(5) 1.61(9) 2.467(4) 160(14) yes
O3 H3 O1 2_666 0.95(4) 1.90(4) 2.788(5) 155(4) yes
C4 H4 S1 2_647 0.9500 2.8600 3.614(5) 137.00 no
C7 H7 O1 . 0.9500 2.4600 2.790(5) 100.00 no
C9 H9A O1 3_455 0.9900 2.5700 3.323(7) 133.00 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
_geom_torsion_publ_flag
C9 S1 C8 S2 . -11.2(3) no
C9 S1 C8 N2 . 168.7(4) no
C8 S1 C9 C10 . 35.8(4) no
C10 S2 C8 S1 . -11.6(3) no
C10 S2 C8 N2 . 168.5(4) no
C8 S2 C10 C9 . 36.2(4) no
O3 Na1 O1 C1 . 60.2(4) no
N2 Na1 O1 C1 . 2.4(3) no
O1 Na1 O1 C1 2_656 -119.8(3) no
N2 Na1 O1 C1 2_656 175.9(3) no
O1 Na1 N2 N1 . -1.8(2) no
O1 Na1 N2 C8 . -171.8(5) no
O3 Na1 N2 N1 . -142.4(2) no
O3 Na1 N2 C8 . 47.6(4) no
O1 Na1 N2 N1 2_656 80.2(3) no
O1 Na1 N2 C8 2_656 -89.8(4) no
Na1 O1 C1 N1 . -2.7(6) no
Na1 O1 C1 C2 . 176.9(3) no
C1 N1 N2 Na1 . 1.5(4) no
C1 N1 N2 C8 . 173.7(4) no
N2 N1 C1 O1 . 0.4(6) no
N2 N1 C1 C2 . -179.2(4) no
Na1 N2 C8 S1 . 163.7(2) no
Na1 N2 C8 S2 . -16.4(6) no
N1 N2 C8 S1 . -5.8(5) no
N1 N2 C8 S2 . 174.1(3) no
O1 C1 C2 C3 . -177.5(4) no
O1 C1 C2 C7 . 0.7(6) no
N1 C1 C2 C3 . 2.1(6) no
N1 C1 C2 C7 . -179.8(4) no
C1 C2 C3 O2 . -2.7(7) no
C1 C2 C3 C4 . 176.8(4) no
C7 C2 C3 O2 . 179.1(4) no
C7 C2 C3 C4 . -1.4(6) no
C1 C2 C7 C6 . -178.4(4) no
C3 C2 C7 C6 . -0.1(7) no
O2 C3 C4 C5 . -179.2(4) no
C2 C3 C4 C5 . 1.3(7) no
C3 C4 C5 C6 . 0.3(8) no
C4 C5 C6 C7 . -1.8(8) no
C5 C6 C7 C2 . 1.7(7) no
S1 C9 C10 S2 . -48.2(4) no
