Di­aqua­bis­(nicotin­amide)­bis(o-sulfobenzimidato-N)­cadmium(II)

The Cd atom in the title compound, [Cd(C₇H₄NO₃S)₂(C₆H₆N₂O)₂(H₂O)₂], lies on an inversion centre and is six-coordinate in an all-trans octahedral geometry. Hydro­gen bonds involving a water mol­ecule and the amido group of a nicotin­amide ligand link adjacent mol­ecules into layers.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.037
• wR factor = 0.096
• Data-to-parameter ratio = 14.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      9
                   N1  -CD1 -N1  -C7     37.00100.00   3.666   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     14
                   N1  -CD1 -N1  -S1   -148.00100.00   3.666   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     21
                   N2  -CD1 -N2  -C12    67.00100.00   3.666   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     26
                   N2  -CD1 -N2  -C8   -114.00100.00   3.666   1.555   1.555   1.555


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 4 Alert Level C = Please check

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S1. Comment

The chemistry of the metal complexes of o-sulfobenzimide (saccharin) revolves around the bonding capabilities of the carbonyl, imido and sulfonyl donor sites (Jovanovski et al., 1990; Jovanovski & Šoptrajanov, 1998; Naumov & Jovanovski, 2000a,b, 2001a,b). The metal o-sulfobenzimidates are themselves Lewis acids that furnish complexes with donor ligands, such as the N-heterocycles. Among these ligands, nicotinamide was selected for an examination of its ability to use its amido end to bind to cadmium; nicotinamide itself is a molecule that is found in a large number of biomolecules. A previous attempt to bind this ligand to the copper derivative resulted in its oxidation to nicotinic acid, which then complexed with the starting copper reagent (Naumov et al., 2001). The corresponding cadmium reactant yielded the expected compound as a centrosymmetric water-coordinated complex. The bonding mode of the anion to the metal atom in the title compound, (I), contrasts with that suggested for the nicotinamide saccharinates [M(C₆H₆N₂O)₂(H₂O)₄](C₇H₄NO₃S)₂ (M = Co, Ni, Zn) and [Cu(C₆H₆N₂O)₂(C₇H₄NO₃S)₂(H₂O)] (˛Cakir et al., 2001).

S2. Experimental

Tetraaquabis(o-sulfobenzimidato)cadmium(II) dihydrate was synthesized by treating cadmium chloride with sodium saccharinate in water. The compound was isolated and then treated with two molar equivalents of nicotinamide in warm water. The crystals that separated from solution were collected and washed with acetone. They contained a small quantity of the starting cadmium compound, as implied by the CHN analytical values.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound at the 50% probability level. H atoms are shown as spheres of arbitrary radii.

Diaquabis(nicotinamide)bis(o-sulfobenzimidato-N)cadmium(II)

Crystal data

[Cd(C7H4NO3S)2·(C6H6N2O)2(H2O)2]	F(000) = 764
Mr = 757.03	Dx = 1.651 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.6547 (1) Å	Cell parameters from 8192 reflections
b = 19.1163 (2) Å	θ = 2.1–28.3°
c = 10.8285 (1) Å	µ = 0.92 mm^−1
β = 106.041 (1)°	T = 298 K
V = 1522.83 (3) Å^3	Parallelepiped, colorless
Z = 2	0.34 × 0.26 × 0.16 mm

Data collection

Siemens CCD area-detector diffractometer	3731 independent reflections
Radiation source: fine-focus sealed tube	3068 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
ω scan	θmax = 28.3°, θmin = 2.1°
Absorption correction: empirical (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.745, Tmax = 0.867	k = −24→25
10747 measured reflections	l = −8→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	All H-atom parameters refined
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0431P)^2] where P = (Fo^2 + 2Fc^2)/3
3731 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −1.48 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cd1	0.5000	0.5000	0.5000	0.0253 (1)
S1	0.55820 (8)	0.34077 (3)	0.66052 (6)	0.0294 (2)
O1	0.4791 (3)	0.3702 (1)	0.7551 (2)	0.046 (1)
O2	0.4365 (3)	0.3013 (1)	0.5619 (2)	0.057 (1)
O3	0.9463 (3)	0.4263 (1)	0.5881 (2)	0.045 (1)
O4	0.9333 (4)	0.4898 (2)	0.1474 (3)	0.093 (1)
O1w	0.7820 (3)	0.5530 (1)	0.5312 (2)	0.041 (1)
N1	0.6595 (3)	0.4016 (1)	0.6010 (2)	0.028 (1)
N2	0.5082 (3)	0.4519 (1)	0.2998 (2)	0.032 (1)
N3	0.7929 (4)	0.4435 (2)	−0.0434 (3)	0.060 (1)
C1	0.7538 (3)	0.2926 (1)	0.7341 (2)	0.033 (1)
C2	0.7736 (5)	0.2331 (2)	0.8101 (3)	0.055 (1)
C3	0.9479 (6)	0.2073 (2)	0.8558 (4)	0.073 (1)
C4	1.0943 (5)	0.2391 (2)	0.8277 (4)	0.070 (1)
C5	1.0728 (4)	0.2990 (2)	0.7533 (3)	0.053 (1)
C6	0.8985 (3)	0.3252 (1)	0.7060 (2)	0.032 (1)
C7	0.8401 (3)	0.3891 (1)	0.6261 (2)	0.030 (1)
C8	0.3753 (4)	0.4083 (2)	0.2374 (3)	0.045 (1)
C9	0.3729 (5)	0.3773 (2)	0.1225 (3)	0.059 (1)
C10	0.5102 (5)	0.3917 (2)	0.0666 (3)	0.053 (1)
C11	0.6476 (4)	0.4370 (2)	0.1283 (3)	0.037 (1)
C12	0.6409 (4)	0.4650 (2)	0.2449 (3)	0.034 (1)
C13	0.8030 (4)	0.4586 (2)	0.0770 (3)	0.050 (1)
H1w1	0.828 (6)	0.570 (2)	0.482 (4)	0.07 (1)*
H1w2	0.853 (7)	0.524 (3)	0.554 (5)	0.08 (2)*
H1n1	0.877 (4)	0.456 (2)	−0.072 (3)	0.04 (1)*
H1n2	0.697 (5)	0.423 (2)	−0.095 (4)	0.06 (1)*
H2	0.675 (5)	0.212 (2)	0.826 (4)	0.07 (1)*
H3	0.975 (6)	0.165 (2)	0.907 (4)	0.09 (1)*
H4	1.215 (6)	0.224 (3)	0.863 (4)	0.11 (2)*
H5	1.167 (5)	0.326 (2)	0.729 (3)	0.05 (1)*
H8	0.279 (4)	0.401 (2)	0.271 (3)	0.04 (1)*
H9	0.284 (6)	0.345 (2)	0.084 (4)	0.08 (1)*
H10	0.515 (4)	0.370 (2)	−0.005 (3)	0.06 (1)*
H12	0.728 (6)	0.496 (2)	0.284 (4)	0.05 (1)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.0259 (1)	0.0294 (2)	0.0244 (2)	0.0025 (1)	0.0132 (1)	0.0031 (1)
S1	0.0222 (3)	0.0331 (3)	0.0303 (3)	−0.0036 (2)	0.0032 (2)	0.0062 (2)
O1	0.036 (1)	0.058 (1)	0.054 (1)	−0.002 (1)	0.027 (1)	0.009 (1)
O2	0.046 (1)	0.053 (1)	0.056 (1)	−0.015 (1)	−0.016 (1)	0.002 (1)
O3	0.035 (1)	0.049 (1)	0.061 (1)	0.002 (1)	0.031 (1)	0.011 (1)
O4	0.071 (2)	0.168 (3)	0.055 (2)	−0.068 (2)	0.042 (2)	−0.052 (2)
O1w	0.033 (1)	0.046 (1)	0.052 (1)	−0.002 (1)	0.025 (1)	0.007 (1)
N1	0.025 (1)	0.031 (1)	0.031 (1)	0.002 (1)	0.012 (1)	0.009 (1)
N2	0.037 (1)	0.036 (1)	0.027 (1)	0.003 (1)	0.017 (1)	0.002 (1)
N3	0.057 (2)	0.093 (2)	0.041 (2)	−0.028 (2)	0.034 (1)	−0.024 (2)
C1	0.032 (1)	0.035 (1)	0.030 (1)	0.003 (1)	0.003 (1)	0.006 (1)
C2	0.056 (2)	0.050 (2)	0.056 (2)	0.002 (2)	0.010 (2)	0.023 (2)
C3	0.074 (3)	0.067 (2)	0.070 (3)	0.025 (2)	0.007 (2)	0.036 (2)
C4	0.051 (2)	0.082 (3)	0.068 (2)	0.032 (2)	−0.001 (2)	0.024 (2)
C5	0.033 (2)	0.068 (2)	0.056 (2)	0.013 (2)	0.009 (1)	0.009 (2)
C6	0.029 (1)	0.037 (1)	0.031 (1)	0.006 (1)	0.007 (1)	0.004 (1)
C7	0.029 (1)	0.034 (1)	0.030 (1)	0.003 (1)	0.014 (1)	0.001 (1)
C8	0.047 (2)	0.057 (2)	0.039 (2)	−0.012 (1)	0.027 (1)	−0.007 (1)
C9	0.065 (2)	0.074 (2)	0.046 (2)	−0.032 (2)	0.028 (2)	−0.022 (2)
C10	0.063 (2)	0.064 (2)	0.040 (2)	−0.021 (2)	0.029 (2)	−0.020 (2)
C11	0.040 (1)	0.045 (2)	0.034 (1)	−0.003 (1)	0.021 (1)	−0.006 (1)
C12	0.037 (1)	0.040 (2)	0.029 (1)	−0.002 (1)	0.016 (1)	−0.004 (1)
C13	0.048 (2)	0.073 (2)	0.039 (2)	−0.013 (2)	0.028 (1)	−0.017 (2)

Geometric parameters (Å, º)

Cd1—O1w	2.323 (2)	C4—C5	1.383 (5)
Cd1—O1w^i	2.323 (2)	C5—C6	1.384 (4)
Cd1—N1	2.343 (2)	C6—C7	1.492 (4)
Cd1—N1^i	2.343 (2)	C8—C9	1.374 (4)
Cd1—N2	2.371 (2)	C9—C10	1.378 (5)
Cd1—N2^i	2.371 (2)	C10—C11	1.383 (4)
S1—O1	1.441 (2)	C11—C12	1.385 (4)
S1—O2	1.424 (2)	C11—C13	1.503 (4)
S1—N1	1.626 (2)	O1w—H1w1	0.78 (4)
S1—C1	1.751 (3)	O1w—H1w2	0.77 (5)
O3—C7	1.233 (3)	N3—H1n1	0.82 (3)
O4—C13	1.229 (4)	N3—H1n2	0.88 (4)
N1—C7	1.355 (3)	C2—H2	0.92 (4)
N2—C12	1.335 (3)	C3—H3	0.97 (5)
N2—C8	1.344 (4)	C4—H4	0.94 (5)
N3—C13	1.317 (4)	C5—H5	0.98 (3)
C1—C6	1.376 (4)	C8—H8	0.91 (3)
C1—C2	1.387 (4)	C9—H9	0.93 (4)
C2—C3	1.380 (5)	C10—H10	0.89 (4)
C3—C4	1.381 (6)	C12—H12	0.90 (4)
O1w—Cd1—O1w^i	180.00 (1)	C5—C6—C7	127.9 (3)
O1w—Cd1—N1	86.51 (8)	O3—C7—N1	124.2 (2)
O1w—Cd1—N1^i	93.49 (8)	O3—C7—C6	123.1 (2)
O1w—Cd1—N2	92.50 (8)	N1—C7—C6	112.7 (2)
O1w—Cd1—N2^i	87.50 (8)	N2—C8—C9	122.9 (3)
O1w^i—Cd1—N1	93.49 (8)	C8—C9—C10	119.3 (3)
O1w^i—Cd1—N1^i	86.51 (8)	C9—C10—C11	118.9 (3)
O1w^i—Cd1—N2	87.50 (8)	C12—C11—C10	117.9 (3)
O1w^i—Cd1—N2^i	92.50 (8)	C12—C11—C13	117.6 (3)
N1—Cd1—N1^i	180.0	C10—C11—C13	124.6 (3)
N1—Cd1—N2	88.49 (7)	N2—C12—C11	123.9 (3)
N1—Cd1—N2^i	91.51 (7)	O4—C13—N3	122.4 (3)
N1^i—Cd1—N2^i	88.49 (7)	O4—C13—C11	119.6 (3)
N1^i—Cd1—N2	91.51 (7)	N3—C13—C11	118.0 (3)
N2—Cd1—N2^i	180.0	Cd1—O1w—H1w1	131 (3)
O2—S1—O1	115.1 (1)	Cd1—O1w—H1w2	107 (4)
O2—S1—N1	111.5 (1)	H1w1—O1w—H1w2	95 (4)
O1—S1—N1	110.0 (1)	C13—N3—H1n1	118 (2)
O2—S1—C1	111.2 (1)	C13—N3—H1n2	122 (2)
O1—S1—C1	110.9 (1)	H1n1—N3—H1n2	120 (3)
N1—S1—C1	96.6 (1)	C3—C2—H2	122 (2)
C7—N1—S1	111.5 (2)	C1—C2—H2	121 (2)
C7—N1—Cd1	127.3 (2)	C2—C3—H3	122 (3)
S1—N1—Cd1	121.0 (1)	C4—C3—H3	116 (3)
C12—N2—C8	117.1 (2)	C5—C4—H4	116 (3)
C12—N2—Cd1	123.4 (2)	C3—C4—H4	122 (3)
C8—N2—Cd1	119.5 (2)	C4—C5—H5	128 (2)
C6—C1—C2	122.7 (3)	C6—C5—H5	115 (2)
C6—C1—S1	107.5 (2)	N2—C8—H8	118 (2)
C2—C1—S1	129.8 (2)	C9—C8—H8	119 (2)
C3—C2—C1	116.2 (3)	C8—C9—H9	121 (3)
C2—C3—C4	121.8 (3)	C10—C9—H9	120 (3)
C5—C4—C3	121.3 (3)	C9—C10—H10	120 (2)
C4—C5—C6	117.6 (3)	C11—C10—H10	121 (2)
C1—C6—C5	120.4 (3)	N2—C12—H12	118 (3)
C1—C6—C7	111.7 (2)	C11—C12—H12	118 (3)
O2—S1—N1—C7	−113.3 (2)	S1—C1—C2—C3	−179.3 (3)
O1—S1—N1—C7	117.8 (2)	C1—C2—C3—C4	0.2 (7)
C1—S1—N1—C7	2.6 (2)	C2—C3—C4—C5	0.7 (8)
O2—S1—N1—Cd1	70.8 (2)	C3—C4—C5—C6	−1.1 (7)
O1—S1—N1—Cd1	−58.1 (2)	C2—C1—C6—C5	0.3 (5)
C1—S1—N1—Cd1	−173.2 (1)	S1—C1—C6—C5	179.2 (2)
O1w^i—Cd1—N1—C7	166.4 (2)	C2—C1—C6—C7	−178.2 (3)
O1w—Cd1—N1—C7	−13.6 (2)	S1—C1—C6—C7	0.6 (3)
N1^i—Cd1—N1—C7	37 (100)	C4—C5—C6—C1	0.6 (5)
N2^i—Cd1—N1—C7	−101.0 (2)	C4—C5—C6—C7	178.9 (3)
N2—Cd1—N1—C7	79.0 (2)	S1—N1—C7—O3	177.7 (2)
O1w^i—Cd1—N1—S1	−18.48 (14)	Cd1—N1—C7—O3	−6.8 (4)
O1w—Cd1—N1—S1	161.5 (1)	S1—N1—C7—C6	−2.6 (3)
N1^i—Cd1—N1—S1	−148 (100)	Cd1—N1—C7—C6	172.9 (2)
N2^i—Cd1—N1—S1	74.1 (1)	C1—C6—C7—O3	−179.1 (3)
N2—Cd1—N1—S1	−105.88 (13)	C5—C6—C7—O3	2.5 (5)
O1w^i—Cd1—N2—C12	175.7 (2)	C1—C6—C7—N1	1.2 (3)
O1w—Cd1—N2—C12	−4.3 (2)	C5—C6—C7—N1	−177.2 (3)
N1—Cd1—N2—C12	−90.7 (2)	C12—N2—C8—C9	0.6 (5)
N1^i—Cd1—N2—C12	89.3 (2)	Cd1—N2—C8—C9	−178.5 (3)
N2^i—Cd1—N2—C12	67 (100)	N2—C8—C9—C10	−1.0 (6)
O1w^i—Cd1—N2—C8	−5.3 (2)	C8—C9—C10—C11	0.4 (6)
O1w—Cd1—N2—C8	174.7 (2)	C9—C10—C11—C12	0.7 (5)
N1—Cd1—N2—C8	88.3 (2)	C9—C10—C11—C13	−178.6 (4)
N1^i—Cd1—N2—C8	−91.7 (2)	C8—N2—C12—C11	0.6 (4)
N2^i—Cd1—N2—C8	−114 (100)	Cd1—N2—C12—C11	179.7 (2)
O2—S1—C1—C6	114.3 (2)	C10—C11—C12—N2	−1.3 (5)
O1—S1—C1—C6	−116.3 (2)	C13—C11—C12—N2	178.1 (3)
N1—S1—C1—C6	−1.9 (2)	C12—C11—C13—O4	12.4 (5)
O2—S1—C1—C2	−67.0 (3)	C10—C11—C13—O4	−168.3 (4)
O1—S1—C1—C2	62.5 (3)	C12—C11—C13—N3	−167.1 (3)
N1—S1—C1—C2	176.9 (3)	C10—C11—C13—N3	12.2 (5)
C6—C1—C2—C3	−0.7 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w2···O3	0.77 (5)	2.00 (5)	2.720 (3)	156 (5)
O1w—H1w1···O3^ii	0.78 (4)	2.07 (5)	2.763 (3)	147 (4)
N3—H1n2···O1^iii	0.88 (4)	2.23 (4)	3.098 (4)	171 (3)
N3—H1n1···O4^iv	0.82 (3)	2.12 (3)	2.931 (4)	167 (3)

Symmetry codes: (ii) −x+2, −y+1, −z+1; (iii) x, y, z−1; (iv) −x+2, −y+1, −z.