Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016728/bt2333sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016728/bt2333Isup2.hkl |
CCDC reference: 646629
Key indicators
- Single-crystal X-ray study
- T = 170 K
- Mean (C-C) = 0.002 Å Some non-H atoms missing
- R factor = 0.035
- wR factor = 0.089
- Data-to-parameter ratio = 18.8
checkCIF/PLATON results
No syntax errors found
Alert level A ABSMU01_ALERT_1_A The ratio of given/expected absorption coefficient lies outside the range 0.90 <> 1.10 Calculated value of mu = 0.287 Value of mu given = 0.573 CHEMW01_ALERT_1_A The ratio of given/expected molecular weight as calculated from the _chemical_formula_sum lies outside the range 0.90 <> 1.10 Calculated formula weight = 309.6560 Formula weight given = 619.3000
Alert level C CHEMW01_ALERT_1_C The difference between the given and expected weight for compound is greater 1 mass unit. Check that all hydrogen atoms have been taken into account. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT335_ALERT_2_C Large Benzene C-C Range ....... C1 -C3_c 0.16 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C3_c ... 1.54 Ang.
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C10 H5 Cl1 N1 Na1 O5 S1 Atom count from _chemical_formula_moiety:C20 H10 Cl2 N2 Na2 O10 S2 FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C10 H5 Cl1 N1 Na1 O5 S1 Atom count from the _atom_site data: C20 H10 Cl2 N2 Na2 O10 S2 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G ALERT: Large difference may be due to a symmetry error - see SYMMG tests From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C10 H5 Cl N Na O5 S TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 40.00 80.00 -40.00 H 20.00 40.00 -20.00 Cl 4.00 8.00 -4.00 N 4.00 8.00 -4.00 Na 4.00 8.00 -4.00 O 20.00 40.00 -20.00 S 4.00 8.00 -4.00
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared by mixing chloroform–methanol (1:1 v/v) solutions (20 and 20 ml, respectively) of saccharin sodium (1.0 mmol) and chloranilic acid (1.0 mmol). The combined solution was left at room temperature for 12 h to give red crystals, which were filtered and washed several times with dichloromethane and then dried.
All H atoms were located in a difference map. The N-bound H atom was refined freely, while other H atoms were refined using a riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).
The NaI atom of the title compound is at the centre of a distorted octahedron and deviates by 0.3422 (8) Å from the mean plane of atoms O1, O2ii, O2iii and O5, which form the equatorial plane (Figs. 1 and 2) [symmetry codes: (ii) -x, -y + 2, -z + 1; (iii) x + 1/2, y + 1/2, z]. The Na—O bond lengths in this plane range from 2.3663 (11) to 2.4024 (11) Å. Atoms O1i and O3iv occupy the axial positions [Na—O1i = 2.4527 (12) and Na—O3iv = 2.5624 (13) Å; symmetry codes: (i) -x + 1/2, -y + 3/2, -z + 1; (iv) x, 1 + y, z].
There is an intermolecular N—H···O hydrogen bond (Table 2). The chloranilate and saccharin ligands bridge the NaI atoms, forming layers parallel to the ab plane at z = 0 and z = 1/2 (Fig. 3).
There are a large number of metal complexes coordinated by the saccharinate anion obtained by deprotonation of the N—H group of saccharin (Baran, 2005; Baran & Yilmaz, 2006; Gumus et al., 2007). However, no crystal data for the metal complex with neutral saccharin as a ligand are available in the Cambridge Structural Database (Version 5.28; Allen, 2002).
Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003).
[Na2(C6Cl2O4)(C7H5NO3S)2] | F(000) = 1248 |
Mr = 619.30 | Dx = 1.818 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -C 2yc | Cell parameters from 10738 reflections |
a = 14.6795 (7) Å | θ = 3.0–30.0° |
b = 6.2247 (3) Å | µ = 0.57 mm−1 |
c = 25.2114 (12) Å | T = 170 K |
β = 99.9052 (16)° | Platelet, red |
V = 2269.36 (19) Å3 | 0.55 × 0.23 × 0.07 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 2886 reflections with I > 2σ(I) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.041 |
ω scans | θmax = 30.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −20→20 |
Tmin = 0.704, Tmax = 0.961 | k = −8→8 |
12067 measured reflections | l = −35→35 |
3306 independent reflections |
Refinement on F2 | 0 restraints |
R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0492P)2 + 1.5311P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3306 reflections | Δρmax = 0.35 e Å−3 |
176 parameters | Δρmin = −0.57 e Å−3 |
[Na2(C6Cl2O4)(C7H5NO3S)2] | V = 2269.36 (19) Å3 |
Mr = 619.30 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 14.6795 (7) Å | µ = 0.57 mm−1 |
b = 6.2247 (3) Å | T = 170 K |
c = 25.2114 (12) Å | 0.55 × 0.23 × 0.07 mm |
β = 99.9052 (16)° |
Rigaku R-AXIS RAPID diffractometer | 3306 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2886 reflections with I > 2σ(I) |
Tmin = 0.704, Tmax = 0.961 | Rint = 0.041 |
12067 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.35 e Å−3 |
3306 reflections | Δρmin = −0.57 e Å−3 |
176 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.04269 (2) | 0.57417 (5) | 0.431471 (13) | 0.01939 (9) | |
S1 | 0.14374 (2) | 0.30306 (6) | 0.354874 (14) | 0.01869 (9) | |
Na1 | 0.27054 (4) | 0.99825 (9) | 0.46736 (2) | 0.01851 (13) | |
O1 | 0.14132 (7) | 0.76727 (16) | 0.47271 (4) | 0.01704 (19) | |
O2 | −0.17515 (7) | 0.85677 (17) | 0.47486 (4) | 0.0179 (2) | |
O3 | 0.13973 (8) | 0.14915 (19) | 0.39671 (5) | 0.0262 (2) | |
O4 | 0.06485 (8) | 0.3162 (2) | 0.31285 (5) | 0.0282 (3) | |
O5 | 0.29399 (8) | 0.77774 (18) | 0.39676 (5) | 0.0255 (2) | |
N1 | 0.17091 (9) | 0.5440 (2) | 0.38105 (5) | 0.0205 (2) | |
C1 | 0.07295 (9) | 0.8707 (2) | 0.48321 (5) | 0.0141 (2) | |
C2 | −0.01884 (9) | 0.8108 (2) | 0.46768 (5) | 0.0152 (2) | |
C3 | −0.09322 (9) | 0.9193 (2) | 0.48437 (5) | 0.0143 (2) | |
C4 | 0.25872 (10) | 0.6137 (2) | 0.37689 (6) | 0.0185 (3) | |
C5 | 0.30221 (10) | 0.4592 (2) | 0.34423 (6) | 0.0190 (3) | |
C6 | 0.38975 (11) | 0.4763 (3) | 0.33085 (6) | 0.0263 (3) | |
H6 | 0.4266 | 0.5962 | 0.3406 | 0.032* | |
C7 | 0.42019 (12) | 0.3072 (3) | 0.30234 (7) | 0.0329 (4) | |
H7 | 0.4792 | 0.3125 | 0.2936 | 0.039* | |
C8 | 0.36383 (13) | 0.1295 (3) | 0.28656 (7) | 0.0324 (4) | |
H8 | 0.3856 | 0.0196 | 0.2671 | 0.039* | |
C9 | 0.27599 (12) | 0.1142 (3) | 0.29944 (6) | 0.0256 (3) | |
H9 | 0.2379 | −0.0028 | 0.2887 | 0.031* | |
C10 | 0.24751 (10) | 0.2814 (2) | 0.32910 (6) | 0.0194 (3) | |
H1 | 0.1459 (17) | 0.599 (4) | 0.4051 (10) | 0.041 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.01556 (15) | 0.01872 (16) | 0.02493 (17) | −0.00330 (12) | 0.00638 (12) | −0.00676 (12) |
S1 | 0.01455 (16) | 0.02209 (17) | 0.02003 (17) | −0.00378 (12) | 0.00463 (12) | 0.00048 (12) |
Na1 | 0.0136 (3) | 0.0178 (3) | 0.0256 (3) | −0.0015 (2) | 0.0077 (2) | −0.0026 (2) |
O1 | 0.0108 (4) | 0.0185 (5) | 0.0231 (5) | 0.0011 (4) | 0.0067 (3) | −0.0014 (4) |
O2 | 0.0092 (4) | 0.0205 (5) | 0.0246 (5) | −0.0033 (4) | 0.0051 (3) | −0.0039 (4) |
O3 | 0.0252 (6) | 0.0282 (6) | 0.0266 (5) | −0.0036 (5) | 0.0081 (4) | 0.0057 (4) |
O4 | 0.0175 (5) | 0.0391 (7) | 0.0265 (6) | −0.0066 (5) | −0.0003 (4) | 0.0015 (5) |
O5 | 0.0258 (6) | 0.0227 (5) | 0.0303 (6) | −0.0070 (4) | 0.0111 (4) | −0.0061 (4) |
N1 | 0.0148 (5) | 0.0229 (6) | 0.0257 (6) | −0.0014 (5) | 0.0089 (5) | −0.0050 (5) |
C1 | 0.0111 (5) | 0.0152 (6) | 0.0172 (5) | −0.0003 (5) | 0.0057 (4) | 0.0008 (5) |
C2 | 0.0114 (5) | 0.0148 (6) | 0.0201 (6) | −0.0020 (5) | 0.0044 (5) | −0.0046 (5) |
C3 | 0.0109 (5) | 0.0158 (6) | 0.0171 (5) | −0.0009 (5) | 0.0047 (4) | −0.0005 (5) |
C4 | 0.0158 (6) | 0.0205 (6) | 0.0204 (6) | −0.0010 (5) | 0.0065 (5) | −0.0002 (5) |
C5 | 0.0168 (6) | 0.0225 (6) | 0.0191 (6) | −0.0012 (5) | 0.0069 (5) | −0.0012 (5) |
C6 | 0.0183 (7) | 0.0362 (8) | 0.0269 (7) | −0.0025 (6) | 0.0104 (6) | −0.0020 (6) |
C7 | 0.0232 (8) | 0.0520 (11) | 0.0268 (8) | 0.0063 (7) | 0.0138 (6) | −0.0025 (7) |
C8 | 0.0338 (9) | 0.0409 (10) | 0.0245 (7) | 0.0117 (8) | 0.0107 (6) | −0.0067 (7) |
C9 | 0.0299 (8) | 0.0254 (7) | 0.0218 (7) | 0.0015 (6) | 0.0057 (6) | −0.0041 (6) |
C10 | 0.0181 (6) | 0.0230 (7) | 0.0180 (6) | 0.0004 (5) | 0.0060 (5) | −0.0005 (5) |
Cl1—C2 | 1.7365 (13) | N1—H1 | 0.84 (3) |
S1—O3 | 1.4336 (12) | C1—C2 | 1.3879 (18) |
S1—O4 | 1.4312 (11) | C1—C3ii | 1.5431 (18) |
S1—N1 | 1.6595 (13) | C2—C3 | 1.4085 (18) |
S1—C10 | 1.7610 (15) | C4—C5 | 1.480 (2) |
Na1—O1 | 2.4024 (11) | C5—C6 | 1.388 (2) |
Na1—O1i | 2.4527 (12) | C5—C10 | 1.382 (2) |
Na1—O2ii | 2.3663 (11) | C6—C7 | 1.391 (2) |
Na1—O2iii | 2.3664 (12) | C6—H6 | 0.93 |
Na1—O3iv | 2.5624 (13) | C7—C8 | 1.398 (3) |
Na1—O5 | 2.3198 (13) | C7—H7 | 0.93 |
O1—C1 | 1.2582 (16) | C8—C9 | 1.386 (3) |
O2—C3 | 1.2475 (15) | C8—H8 | 0.93 |
O5—C4 | 1.2134 (19) | C9—C10 | 1.387 (2) |
N1—C4 | 1.3810 (18) | C9—H9 | 0.93 |
Na1···Cl1iii | 3.0680 (7) | Na1···Na1i | 3.6006 (12) |
Na1···C1 | 3.0986 (14) | Na1···Na1v | 3.6381 (11) |
Na1···C3ii | 3.0998 (14) | ||
O4—S1—O3 | 116.90 (7) | S1—N1—H1 | 123.7 (18) |
O4—S1—N1 | 110.57 (7) | O1—C1—C2 | 125.03 (12) |
O3—S1—N1 | 110.42 (7) | O1—C1—C3ii | 117.17 (11) |
O4—S1—C10 | 111.86 (7) | C2—C1—C3ii | 117.80 (11) |
O3—S1—C10 | 111.58 (7) | C1—C2—C3 | 123.49 (12) |
N1—S1—C10 | 92.98 (7) | C1—C2—Cl1 | 118.31 (10) |
O1—Na1—O1i | 84.27 (4) | C3—C2—Cl1 | 117.86 (10) |
O2ii—Na1—O1 | 68.72 (4) | O2—C3—C2 | 124.33 (12) |
O2iii—Na1—O1 | 144.92 (4) | O2—C3—C1ii | 117.26 (11) |
O2ii—Na1—O1i | 100.55 (4) | C2—C3—C1ii | 118.41 (11) |
O2iii—Na1—O1i | 116.84 (4) | O5—C4—N1 | 124.78 (14) |
O5—Na1—O1 | 84.94 (4) | O5—C4—C5 | 125.61 (14) |
O5—Na1—O1i | 86.66 (4) | N1—C4—C5 | 109.61 (12) |
O2ii—Na1—O2iii | 79.52 (4) | C10—C5—C6 | 120.85 (14) |
O5—Na1—O2ii | 151.60 (5) | C10—C5—C4 | 112.84 (13) |
O5—Na1—O2iii | 121.79 (5) | C6—C5—C4 | 126.25 (14) |
O1—Na1—O3iv | 75.75 (4) | C5—C6—C7 | 117.44 (16) |
O1i—Na1—O3iv | 158.14 (4) | C5—C6—H6 | 121.3 |
O2ii—Na1—O3iv | 80.56 (4) | C7—C6—H6 | 121.3 |
O2iii—Na1—O3iv | 84.93 (4) | C6—C7—C8 | 121.27 (16) |
O5—Na1—O3iv | 82.87 (5) | C6—C7—H7 | 119.4 |
Na1—O1—Na1i | 95.73 (4) | C8—C7—H7 | 119.4 |
C1—O1—Na1 | 111.82 (9) | C9—C8—C7 | 121.09 (15) |
C1—O1—Na1i | 124.80 (9) | C9—C8—H8 | 119.5 |
C3—O2—Na1ii | 114.55 (9) | C7—C8—H8 | 119.5 |
C3—O2—Na1vi | 127.60 (9) | C8—C9—C10 | 116.99 (15) |
Na1ii—O2—Na1vi | 100.48 (4) | C8—C9—H9 | 121.5 |
S1—O3—Na1vii | 129.47 (7) | C10—C9—H9 | 121.5 |
C4—O5—Na1 | 134.88 (10) | C5—C10—C9 | 122.33 (14) |
C4—N1—S1 | 114.67 (10) | C5—C10—S1 | 109.58 (11) |
C4—N1—H1 | 117.3 (17) | C9—C10—S1 | 128.06 (12) |
O5—Na1—O1—C1 | −141.72 (9) | Na1vi—O2—C3—C1ii | −147.38 (9) |
O2ii—Na1—O1—C1 | 27.46 (9) | Na1vi—O2—C3—Na1ii | −127.17 (13) |
O2iii—Na1—O1—C1 | 0.86 (13) | C1—C2—C3—O2 | −173.24 (13) |
O1i—Na1—O1—C1 | 131.15 (10) | Cl1—C2—C3—O2 | −0.03 (19) |
O3iv—Na1—O1—C1 | −57.80 (9) | C1—C2—C3—C1ii | 6.5 (2) |
O5—Na1—O1—Na1i | 87.14 (4) | Cl1—C2—C3—C1ii | 179.74 (9) |
O2ii—Na1—O1—Na1i | −103.69 (4) | C1—C2—C3—Na1ii | −126.4 (2) |
O2iii—Na1—O1—Na1i | −130.29 (7) | Cl1—C2—C3—Na1ii | 46.8 (3) |
O1i—Na1—O1—Na1i | 0.0 | Na1—O5—C4—N1 | 22.3 (2) |
O3iv—Na1—O1—Na1i | 171.05 (5) | Na1—O5—C4—C5 | −158.35 (11) |
O4—S1—O3—Na1vii | 164.12 (8) | S1—N1—C4—O5 | −174.54 (12) |
N1—S1—O3—Na1vii | −68.34 (10) | S1—N1—C4—C5 | 5.99 (16) |
C10—S1—O3—Na1vii | 33.61 (11) | O5—C4—C5—C10 | 176.99 (14) |
O2ii—Na1—O5—C4 | −26.6 (2) | N1—C4—C5—C10 | −3.55 (18) |
O2iii—Na1—O5—C4 | −160.78 (14) | O5—C4—C5—C6 | −0.2 (3) |
O1—Na1—O5—C4 | −5.05 (15) | N1—C4—C5—C6 | 179.24 (15) |
O1i—Na1—O5—C4 | 79.49 (15) | C10—C5—C6—C7 | −0.7 (2) |
O3iv—Na1—O5—C4 | −81.28 (15) | C4—C5—C6—C7 | 176.30 (15) |
O4—S1—N1—C4 | −120.06 (11) | C5—C6—C7—C8 | 1.6 (3) |
O3—S1—N1—C4 | 108.99 (12) | C6—C7—C8—C9 | −0.9 (3) |
C10—S1—N1—C4 | −5.37 (12) | C7—C8—C9—C10 | −0.8 (3) |
Na1—O1—C1—C2 | 151.68 (11) | C6—C5—C10—C9 | −1.0 (2) |
Na1i—O1—C1—C2 | −94.16 (15) | C4—C5—C10—C9 | −178.39 (14) |
Na1—O1—C1—C3ii | −28.03 (14) | C6—C5—C10—S1 | 177.20 (12) |
Na1i—O1—C1—C3ii | 86.12 (13) | C4—C5—C10—S1 | −0.18 (16) |
Na1i—O1—C1—Na1 | 114.16 (11) | C8—C9—C10—C5 | 1.7 (2) |
O1—C1—C2—C3 | 173.81 (13) | C8—C9—C10—S1 | −176.12 (13) |
C3ii—C1—C2—C3 | −6.5 (2) | O4—S1—C10—C5 | 116.60 (11) |
O1—C1—C2—Cl1 | 0.62 (19) | O3—S1—C10—C5 | −110.32 (11) |
C3ii—C1—C2—Cl1 | −179.67 (9) | N1—S1—C10—C5 | 3.03 (12) |
Na1ii—O2—C3—C2 | 159.56 (11) | O4—S1—C10—C9 | −65.31 (16) |
Na1vi—O2—C3—C2 | 32.39 (19) | O3—S1—C10—C9 | 67.76 (15) |
Na1ii—O2—C3—C1ii | −20.21 (14) | N1—S1—C10—C9 | −178.89 (14) |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) −x, −y+2, −z+1; (iii) x+1/2, y+1/2, z; (iv) x, y+1, z; (v) −x+1/2, −y+5/2, −z+1; (vi) x−1/2, y−1/2, z; (vii) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.84 (3) | 2.01 (2) | 2.7938 (16) | 156 (2) |
Experimental details
Crystal data | |
Chemical formula | [Na2(C6Cl2O4)(C7H5NO3S)2] |
Mr | 619.30 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 170 |
a, b, c (Å) | 14.6795 (7), 6.2247 (3), 25.2114 (12) |
β (°) | 99.9052 (16) |
V (Å3) | 2269.36 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.57 |
Crystal size (mm) | 0.55 × 0.23 × 0.07 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.704, 0.961 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12067, 3306, 2886 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.089, 1.05 |
No. of reflections | 3306 |
No. of parameters | 176 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.35, −0.57 |
Computer programs: PROCESS-AUTO (Rigaku/MSC, 2004), PROCESS-AUTO, CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), CrystalStructure and PLATON (Spek, 2003).
Na1—O1 | 2.4024 (11) | Na1—O2iii | 2.3664 (12) |
Na1—O1i | 2.4527 (12) | Na1—O3iv | 2.5624 (13) |
Na1—O2ii | 2.3663 (11) | Na1—O5 | 2.3198 (13) |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) −x, −y+2, −z+1; (iii) x+1/2, y+1/2, z; (iv) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.84 (3) | 2.01 (2) | 2.7938 (16) | 156 (2) |
The NaI atom of the title compound is at the centre of a distorted octahedron and deviates by 0.3422 (8) Å from the mean plane of atoms O1, O2ii, O2iii and O5, which form the equatorial plane (Figs. 1 and 2) [symmetry codes: (ii) -x, -y + 2, -z + 1; (iii) x + 1/2, y + 1/2, z]. The Na—O bond lengths in this plane range from 2.3663 (11) to 2.4024 (11) Å. Atoms O1i and O3iv occupy the axial positions [Na—O1i = 2.4527 (12) and Na—O3iv = 2.5624 (13) Å; symmetry codes: (i) -x + 1/2, -y + 3/2, -z + 1; (iv) x, 1 + y, z].
There is an intermolecular N—H···O hydrogen bond (Table 2). The chloranilate and saccharin ligands bridge the NaI atoms, forming layers parallel to the ab plane at z = 0 and z = 1/2 (Fig. 3).