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
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).