Bis[2-(benzimidazol-2-ylsulfan-yl)acetato]bis-(2,2'-bipyridine)cadmium(II).

In the structure of the title compound, [Cd(C(9)H(7)N(2)O(2)S)(2)(C(10)H(8)N(2))(2)], the complex mol-ecules are located on a crystallographic twofold rotation axis and the Cd(II) ion is octa-hedrally coordinated by two chelating 2,2'-bipyridine ligands and two O atoms from the carboxyl-ate groups of two 2-(benzimidazol-2-ylsulfan-yl)acetate ligands. The two carboxyl-ate ligands adopt a cis configuration with respect to each other. Within each of these ligands, the imidazole fragments are bent back in a loop towards the acetyl groups, forming intra-molecular N-H⋯O hydrogen bonds, which help to stablilize the mononuclear complex. Adjacent mol-ecules are further linked by weak C-H⋯O hydrogen bonds, resulting in a chain along the c axis.

Related literature

For related structures, see: Matthews et al. (1998 ▶); Cheng et al. (2009 ▶).

Experimental

Crystal data

[Cd(C9H7N2O2S)2(C10H8N2)2]

M = 839.25

Monoclinic,

a = 26.733 (2) Å

b = 9.3043 (8) Å

c = 16.4220 (14) Å

β = 120.2540 (10)°

V = 3528.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.79 mm−1

T = 295 K

0.20 × 0.18 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.858, T max = 0.911

9308 measured reflections

3460 independent reflections

2946 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.069

S = 1.05

3460 reflections

244 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.47 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809039592/zl2228sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039592/zl2228Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cd(C9H7N2O2S)2(C10H8N2)2]	F(000) = 1704
Mr = 839.25	Dx = 1.580 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 783 reflections
a = 26.733 (2) Å	θ = 2.4–28.0°
b = 9.3043 (8) Å	µ = 0.79 mm−1
c = 16.4220 (14) Å	T = 295 K
β = 120.254 (1)°	Block, colorless
V = 3528.3 (5) Å3	0.20 × 0.18 × 0.12 mm
Z = 4

Bruker SMART CCD diffractometer	3460 independent reflections
Radiation source: fine-focus sealed tube	2946 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −32→30
Tmin = 0.858, Tmax = 0.911	k = −11→11
9308 measured reflections	l = −20→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0305P)2 + 1.2632P] where P = (Fo2 + 2Fc2)/3
3460 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

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
Cd1	0.0000	0.27478 (3)	0.2500	0.03543 (10)
S1	0.15271 (3)	0.05110 (8)	0.52528 (4)	0.04872 (19)
C1	0.03416 (10)	0.1120 (3)	0.43699 (17)	0.0373 (6)
C2	0.08216 (10)	0.0184 (3)	0.51125 (16)	0.0415 (6)
H2A	0.0721	−0.0817	0.4945	0.050*
H2B	0.0843	0.0346	0.5713	0.050*
C3	0.15201 (10)	−0.0542 (3)	0.43638 (16)	0.0388 (6)
C4	0.17937 (11)	−0.1829 (3)	0.35876 (17)	0.0413 (6)
C5	0.20952 (13)	−0.2670 (3)	0.3279 (2)	0.0540 (7)
H5A	0.2493	−0.2809	0.3653	0.065*
C6	0.17850 (13)	−0.3294 (3)	0.2399 (2)	0.0567 (7)
H6A	0.1979	−0.3860	0.2179	0.068*
C7	0.11932 (13)	−0.3099 (3)	0.1835 (2)	0.0561 (8)
H7A	0.1000	−0.3523	0.1242	0.067*
C8	0.08838 (13)	−0.2290 (3)	0.2134 (2)	0.0524 (7)
H8A	0.0486	−0.2163	0.1759	0.063*
C9	0.11938 (10)	−0.1676 (3)	0.30194 (16)	0.0385 (6)
C10	0.03449 (11)	0.5176 (3)	0.4126 (2)	0.0494 (7)
H10A	−0.0049	0.5104	0.3915	0.059*
C11	0.06748 (12)	0.6067 (3)	0.4870 (2)	0.0539 (7)
H11A	0.0511	0.6576	0.5166	0.065*
C12	0.12519 (12)	0.6190 (3)	0.5169 (2)	0.0526 (7)
H12A	0.1485	0.6799	0.5667	0.063*
C13	0.14864 (11)	0.5405 (3)	0.47287 (18)	0.0456 (6)
H13A	0.1878	0.5479	0.4924	0.055*
C14	0.11277 (9)	0.4506 (2)	0.39904 (16)	0.0336 (5)
C15	0.13512 (9)	0.3589 (3)	0.35035 (16)	0.0339 (5)
C16	0.19346 (11)	0.3488 (3)	0.3800 (2)	0.0542 (7)
H16A	0.2203	0.4034	0.4307	0.065*
C17	0.21161 (12)	0.2577 (3)	0.3340 (2)	0.0634 (9)
H17A	0.2508	0.2496	0.3537	0.076*
C18	0.17124 (11)	0.1788 (3)	0.2589 (2)	0.0525 (7)
H18A	0.1824	0.1166	0.2266	0.063*
C19	0.11432 (11)	0.1940 (3)	0.23272 (18)	0.0454 (7)
H19A	0.0869	0.1410	0.1817	0.055*
N1	0.19912 (8)	−0.1097 (2)	0.44392 (15)	0.0478 (5)
N2	0.10299 (9)	−0.0851 (2)	0.35415 (14)	0.0410 (5)
N3	0.05612 (8)	0.4404 (2)	0.36884 (14)	0.0390 (5)
N4	0.09607 (8)	0.2814 (2)	0.27686 (14)	0.0360 (5)
O1	0.01181 (8)	0.2029 (2)	0.46217 (13)	0.0559 (5)
O2	0.02068 (7)	0.08785 (18)	0.35135 (11)	0.0422 (4)
H2C	0.0731 (11)	−0.046 (3)	0.3391 (17)	0.040 (7)*

	U11	U22	U33	U12	U13	U23
Cd1	0.02273 (14)	0.04258 (17)	0.03763 (15)	0.000	0.01272 (11)	0.000
S1	0.0323 (3)	0.0634 (5)	0.0415 (4)	0.0011 (3)	0.0120 (3)	−0.0134 (3)
C1	0.0281 (12)	0.0453 (15)	0.0395 (14)	0.0012 (11)	0.0178 (11)	0.0034 (12)
C2	0.0437 (14)	0.0473 (16)	0.0351 (13)	0.0069 (12)	0.0211 (12)	0.0061 (11)
C3	0.0293 (13)	0.0463 (15)	0.0354 (13)	0.0004 (11)	0.0123 (11)	−0.0007 (11)
C4	0.0352 (13)	0.0485 (16)	0.0412 (14)	0.0000 (11)	0.0199 (12)	0.0005 (12)
C5	0.0413 (16)	0.067 (2)	0.0592 (18)	0.0054 (13)	0.0293 (15)	−0.0053 (15)
C6	0.0614 (19)	0.0594 (19)	0.0638 (19)	0.0036 (15)	0.0424 (17)	−0.0084 (16)
C7	0.064 (2)	0.0568 (19)	0.0482 (17)	−0.0032 (15)	0.0289 (15)	−0.0110 (14)
C8	0.0430 (16)	0.0599 (18)	0.0452 (16)	0.0030 (13)	0.0154 (13)	−0.0044 (14)
C9	0.0357 (13)	0.0404 (14)	0.0376 (13)	0.0031 (11)	0.0170 (11)	0.0038 (11)
C10	0.0418 (15)	0.0446 (16)	0.0701 (18)	0.0026 (12)	0.0344 (14)	−0.0066 (14)
C11	0.0633 (19)	0.0424 (16)	0.0722 (19)	0.0020 (14)	0.0462 (17)	−0.0104 (15)
C12	0.0540 (17)	0.0482 (17)	0.0573 (17)	−0.0067 (13)	0.0293 (15)	−0.0161 (14)
C13	0.0363 (14)	0.0483 (16)	0.0512 (15)	−0.0059 (12)	0.0213 (12)	−0.0138 (13)
C14	0.0288 (12)	0.0340 (13)	0.0379 (13)	0.0002 (10)	0.0167 (11)	0.0002 (10)
C15	0.0275 (12)	0.0379 (14)	0.0362 (13)	−0.0033 (10)	0.0160 (10)	−0.0032 (11)
C16	0.0296 (13)	0.070 (2)	0.0594 (17)	−0.0091 (13)	0.0196 (13)	−0.0281 (15)
C17	0.0293 (14)	0.088 (2)	0.073 (2)	−0.0054 (14)	0.0259 (15)	−0.0318 (18)
C18	0.0393 (15)	0.0666 (19)	0.0589 (17)	−0.0006 (13)	0.0302 (14)	−0.0177 (15)
C19	0.0373 (14)	0.0567 (18)	0.0443 (15)	−0.0087 (12)	0.0220 (12)	−0.0163 (13)
N1	0.0295 (11)	0.0618 (15)	0.0459 (13)	0.0042 (10)	0.0144 (10)	−0.0054 (11)
N2	0.0281 (11)	0.0496 (14)	0.0393 (12)	0.0059 (10)	0.0126 (10)	−0.0043 (10)
N3	0.0297 (11)	0.0404 (12)	0.0491 (12)	0.0008 (9)	0.0215 (10)	−0.0055 (10)
N4	0.0267 (10)	0.0443 (12)	0.0366 (11)	−0.0027 (9)	0.0156 (9)	−0.0065 (9)
O1	0.0470 (11)	0.0704 (14)	0.0491 (11)	0.0212 (10)	0.0234 (9)	−0.0027 (10)
O2	0.0393 (9)	0.0521 (11)	0.0332 (9)	0.0121 (8)	0.0168 (8)	0.0054 (8)

Cd1—O2i	2.2746 (16)	C8—H8A	0.9300
Cd1—O2	2.2746 (16)	C9—N2	1.376 (3)
Cd1—N3	2.342 (2)	C10—N3	1.336 (3)
Cd1—N3i	2.3417 (19)	C10—C11	1.369 (4)
Cd1—N4i	2.3775 (19)	C10—H10A	0.9300
Cd1—N4	2.3775 (19)	C11—C12	1.368 (4)
S1—C3	1.750 (2)	C11—H11A	0.9300
S1—C2	1.807 (2)	C12—C13	1.381 (3)
C1—O1	1.221 (3)	C12—H12A	0.9300
C1—O2	1.284 (3)	C13—C14	1.385 (3)
C1—C2	1.521 (3)	C13—H13A	0.9300
C2—H2A	0.9700	C14—N3	1.338 (3)
C2—H2B	0.9700	C14—C15	1.485 (3)
C3—N1	1.308 (3)	C15—N4	1.340 (3)
C3—N2	1.357 (3)	C15—C16	1.383 (3)
C4—C5	1.389 (4)	C16—C17	1.375 (4)
C4—N1	1.398 (3)	C16—H16A	0.9300
C4—C9	1.398 (3)	C17—C18	1.373 (4)
C5—C6	1.381 (4)	C17—H17A	0.9300
C5—H5A	0.9300	C18—C19	1.364 (3)
C6—C7	1.385 (4)	C18—H18A	0.9300
C6—H6A	0.9300	C19—N4	1.335 (3)
C7—C8	1.378 (4)	C19—H19A	0.9300
C7—H7A	0.9300	N2—H2C	0.80 (2)
C8—C9	1.383 (4)
O2i—Cd1—O2	80.25 (8)	N2—C9—C4	105.0 (2)
O2i—Cd1—N3	158.50 (6)	C8—C9—C4	122.5 (2)
O2—Cd1—N3	94.35 (7)	N3—C10—C11	123.2 (2)
O2i—Cd1—N3i	94.35 (7)	N3—C10—H10A	118.4
O2—Cd1—N3i	158.50 (6)	C11—C10—H10A	118.4
N3—Cd1—N3i	97.71 (10)	C12—C11—C10	118.3 (2)
O2i—Cd1—N4i	92.44 (6)	C12—C11—H11A	120.9
O2—Cd1—N4i	89.84 (6)	C10—C11—H11A	120.9
N3—Cd1—N4i	108.43 (7)	C11—C12—C13	119.7 (3)
N3i—Cd1—N4i	69.49 (6)	C11—C12—H12A	120.1
O2i—Cd1—N4	89.84 (6)	C13—C12—H12A	120.1
O2—Cd1—N4	92.44 (6)	C12—C13—C14	118.8 (2)
N3—Cd1—N4	69.49 (6)	C12—C13—H13A	120.6
N3i—Cd1—N4	108.43 (7)	C14—C13—H13A	120.6
N4i—Cd1—N4	177.01 (10)	N3—C14—C13	121.5 (2)
C3—S1—C2	103.15 (12)	N3—C14—C15	116.5 (2)
O1—C1—O2	125.2 (2)	C13—C14—C15	122.0 (2)
O1—C1—C2	118.9 (2)	N4—C15—C16	120.6 (2)
O2—C1—C2	115.8 (2)	N4—C15—C14	116.84 (19)
C1—C2—S1	114.25 (17)	C16—C15—C14	122.5 (2)
C1—C2—H2A	108.7	C17—C16—C15	119.7 (2)
S1—C2—H2A	108.7	C17—C16—H16A	120.1
C1—C2—H2B	108.7	C15—C16—H16A	120.1
S1—C2—H2B	108.7	C18—C17—C16	119.2 (3)
H2A—C2—H2B	107.6	C18—C17—H17A	120.4
N1—C3—N2	114.3 (2)	C16—C17—H17A	120.4
N1—C3—S1	122.47 (18)	C19—C18—C17	118.3 (2)
N2—C3—S1	123.23 (18)	C19—C18—H18A	120.8
C5—C4—N1	130.0 (2)	C17—C18—H18A	120.8
C5—C4—C9	119.7 (2)	N4—C19—C18	123.2 (2)
N1—C4—C9	110.2 (2)	N4—C19—H19A	118.4
C6—C5—C4	117.8 (3)	C18—C19—H19A	118.4
C6—C5—H5A	121.1	C3—N1—C4	103.73 (19)
C4—C5—H5A	121.1	C3—N2—C9	106.7 (2)
C5—C6—C7	121.7 (3)	C3—N2—H2C	121.9 (18)
C5—C6—H6A	119.1	C9—N2—H2C	130.3 (18)
C7—C6—H6A	119.1	C10—N3—C14	118.6 (2)
C8—C7—C6	121.5 (3)	C10—N3—Cd1	122.20 (16)
C8—C7—H7A	119.3	C14—N3—Cd1	119.05 (15)
C6—C7—H7A	119.3	C19—N4—C15	119.0 (2)
C7—C8—C9	116.8 (3)	C19—N4—Cd1	122.67 (16)
C7—C8—H8A	121.6	C15—N4—Cd1	117.36 (14)
C9—C8—H8A	121.6	C1—O2—Cd1	119.90 (16)
N2—C9—C8	132.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···O2	0.80 (2)	1.96 (2)	2.708 (3)	156 (2)
C11—H11A···O1ii	0.93	2.29	3.179 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2C⋯O2	0.80 (2)	1.96 (2)	2.708 (3)	156 (2)
C11—H11A⋯O1i	0.93	2.29	3.179 (3)	161

Symmetry code: (i) .