Bis[4-(2-hy-droxy-benzyl-idene-amino)-benzoato-κO]tetra-kis-(methanol-κO)cadmium.

In the title mononuclear complex, [Cd(C(14)H(10)NO(3))(2)(CH(3)OH)(4)], the Cd(2+) cation is situated on an inversion centre. It exhibits a distorted octa-hedral coordination, defined by two carboxyl-ate O atoms from two monodentate anions and by four O atoms from four methanol mol-ecules. The crystal structure comprises intra-molecular O-H⋯O and O-H⋯N, and inter-molecular O-H⋯O hydrogen bonds. The latter help to construct a layered structure extending parallel to (100).

Related literature

For background to Schiff base ligands, see: Garnovskii et al. (1993 ▶); Banerjee et al. (2004 ▶); Zhong et al. (2009 ▶). For background to cadmium complexes, see: Meng et al. (2004 ▶); Wang et al. (2010 ▶).

Experimental

Crystal data

[Cd(C14H10NO3)2(CH4O)4]

M = 721.04

Monoclinic,

a = 15.564 (3) Å

b = 11.937 (2) Å

c = 8.8946 (18) Å

β = 99.69 (3)°

V = 1629.0 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.73 mm−1

T = 293 K

0.21 × 0.19 × 0.16 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ▶) T min = 0.862, T max = 0.892

7793 measured reflections

2760 independent reflections

2137 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.166

S = 1.13

2760 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.97 e Å−3

Δρmin = −0.63 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015364/wm2478sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015364/wm2478Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811015364/wm2478Isup3.cdx

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

[Cd(C14H10NO3)2(CH4O)4]	F(000) = 740
Mr = 721.04	Dx = 1.470 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3109 reflections
a = 15.564 (3) Å	θ = 2.2–28.0°
b = 11.937 (2) Å	µ = 0.73 mm−1
c = 8.8946 (18) Å	T = 293 K
β = 99.69 (3)°	Prism, pale yellow
V = 1629.0 (6) Å3	0.21 × 0.19 × 0.16 mm
Z = 2

Rigaku Saturn diffractometer	2760 independent reflections
Radiation source: fine-focus sealed tube	2137 reflections with I > 2σ(I)
graphite	Rint = 0.055
Detector resolution: 28.5714 pixels mm-1	θmax = 25.0°, θmin = 2.2°
ω scans	h = −18→18
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −14→10
Tmin = 0.862, Tmax = 0.892	l = −10→9
7793 measured reflections

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0483P)2 + 5.4285P] where P = (Fo2 + 2Fc2)/3
2760 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.97 e Å−3
0 restraints	Δρmin = −0.63 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	1.0000	0.5000	1.5000	0.0478 (3)
N1	0.5587 (4)	0.4273 (6)	0.7851 (7)	0.0592 (17)
O1	0.8888 (4)	0.4749 (4)	1.3094 (6)	0.0591 (15)
O2	0.9173 (4)	0.3047 (4)	1.2333 (7)	0.0740 (18)
O3	1.0768 (4)	0.5897 (4)	1.3338 (6)	0.0684 (16)
H3	1.0698	0.6603	1.3269	0.103*
O4	1.0614 (3)	0.3361 (4)	1.4350 (6)	0.0605 (14)
H4	1.0252	0.3053	1.3620	0.091*
O5	0.4108 (4)	0.5348 (5)	0.7011 (8)	0.0810 (19)
H5	0.4577	0.5198	0.7542	0.122*
C1	0.8710 (5)	0.3913 (6)	1.2257 (8)	0.0513 (18)
C2	0.7912 (5)	0.3969 (6)	1.1089 (7)	0.0467 (17)
C3	0.7585 (5)	0.3037 (6)	1.0221 (9)	0.062 (2)
H3A	0.7881	0.2358	1.0373	0.075*
C4	0.6827 (5)	0.3101 (6)	0.9135 (9)	0.066 (2)
H4A	0.6622	0.2472	0.8570	0.079*
C5	0.6378 (5)	0.4124 (6)	0.8902 (8)	0.0519 (19)
C6	0.6693 (5)	0.5042 (7)	0.9765 (9)	0.061 (2)
H6	0.6398	0.5722	0.9619	0.073*
C7	0.7443 (6)	0.4964 (6)	1.0843 (8)	0.062 (2)
H7	0.7638	0.5592	1.1419	0.074*
C8	0.5382 (5)	0.3639 (7)	0.6702 (9)	0.063 (2)
H8	0.5776	0.3100	0.6491	0.076*
C9	0.4532 (5)	0.3738 (7)	0.5696 (9)	0.059 (2)
C10	0.4316 (6)	0.2979 (8)	0.4527 (10)	0.076 (3)
H10	0.4725	0.2449	0.4347	0.092*
C11	0.3504 (7)	0.2990 (8)	0.3616 (11)	0.084 (3)
H11	0.3353	0.2445	0.2870	0.101*
C12	0.2932 (6)	0.3808 (9)	0.3826 (11)	0.082 (3)
H12	0.2400	0.3841	0.3170	0.099*
C13	0.3112 (6)	0.4603 (8)	0.4994 (11)	0.076 (3)
H13	0.2700	0.5136	0.5149	0.091*
C14	0.3917 (6)	0.4568 (7)	0.5904 (9)	0.062 (2)
C15	1.0839 (5)	0.5457 (5)	1.1902 (7)	0.091 (3)
H15A	1.1181	0.5955	1.1392	0.137*
H15B	1.0269	0.5378	1.1305	0.137*
H15C	1.1118	0.4738	1.2027	0.137*
C16	1.1049 (5)	0.2536 (5)	1.5305 (7)	0.079 (3)
H16A	1.1236	0.1942	1.4708	0.118*
H16B	1.0663	0.2241	1.5943	0.118*
H16C	1.1547	0.2867	1.5931	0.118*

	U11	U22	U33	U12	U13	U23
Cd1	0.0584 (5)	0.0351 (4)	0.0469 (4)	0.0027 (4)	0.0006 (3)	−0.0028 (3)
N1	0.055 (4)	0.069 (4)	0.053 (4)	0.000 (3)	0.004 (3)	0.003 (3)
O1	0.064 (4)	0.047 (3)	0.061 (3)	0.006 (2)	−0.005 (3)	−0.015 (2)
O2	0.073 (4)	0.047 (3)	0.090 (4)	0.010 (3)	−0.022 (3)	−0.015 (3)
O3	0.098 (5)	0.048 (3)	0.063 (3)	−0.011 (3)	0.023 (3)	0.006 (2)
O4	0.063 (4)	0.043 (3)	0.069 (3)	0.011 (2)	−0.006 (3)	−0.008 (2)
O5	0.064 (4)	0.086 (4)	0.094 (5)	0.018 (3)	0.015 (4)	−0.003 (3)
C1	0.060 (5)	0.047 (4)	0.046 (4)	−0.004 (4)	0.005 (4)	0.000 (3)
C2	0.045 (4)	0.054 (4)	0.041 (4)	−0.008 (3)	0.006 (3)	−0.001 (3)
C3	0.066 (6)	0.046 (4)	0.069 (5)	0.001 (4)	−0.004 (4)	−0.003 (4)
C4	0.066 (6)	0.053 (4)	0.068 (5)	−0.007 (4)	−0.018 (4)	−0.006 (4)
C5	0.051 (5)	0.060 (5)	0.045 (4)	−0.001 (4)	0.006 (4)	0.008 (3)
C6	0.064 (5)	0.059 (4)	0.056 (5)	0.006 (4)	−0.001 (4)	0.000 (4)
C7	0.085 (6)	0.050 (4)	0.045 (4)	0.000 (4)	−0.007 (4)	0.001 (3)
C8	0.057 (5)	0.067 (5)	0.065 (5)	0.004 (4)	0.008 (4)	0.003 (4)
C9	0.043 (5)	0.070 (5)	0.060 (5)	−0.007 (4)	0.001 (4)	0.013 (4)
C10	0.078 (7)	0.072 (6)	0.074 (6)	−0.002 (5)	−0.002 (5)	−0.003 (5)
C11	0.078 (7)	0.082 (7)	0.085 (7)	−0.013 (6)	−0.007 (6)	−0.007 (5)
C12	0.061 (6)	0.097 (7)	0.082 (7)	−0.010 (5)	−0.010 (5)	0.022 (6)
C13	0.056 (6)	0.085 (6)	0.085 (7)	0.011 (5)	0.005 (5)	0.013 (5)
C14	0.057 (6)	0.076 (5)	0.055 (5)	−0.009 (4)	0.012 (4)	0.000 (4)
C15	0.137 (10)	0.059 (5)	0.084 (7)	0.012 (6)	0.036 (7)	0.005 (5)
C16	0.085 (7)	0.055 (5)	0.096 (7)	0.023 (5)	0.016 (6)	0.020 (5)

Cd1—O1	2.230 (5)	C5—C6	1.380 (10)
Cd1—O1i	2.230 (5)	C6—C7	1.384 (11)
Cd1—O4i	2.295 (5)	C6—H6	0.9300
Cd1—O4	2.295 (5)	C7—H7	0.9300
Cd1—O3i	2.315 (5)	C8—C9	1.472 (10)
Cd1—O3	2.315 (5)	C8—H8	0.9300
N1—C8	1.270 (9)	C9—C10	1.377 (11)
N1—C5	1.425 (9)	C9—C14	1.412 (11)
O1—C1	1.248 (8)	C10—C11	1.382 (12)
O2—C1	1.255 (8)	C10—H10	0.9300
O3—C15	1.403 (8)	C11—C12	1.356 (13)
O3—H3	0.8507	C11—H11	0.9300
O4—C16	1.398 (7)	C12—C13	1.401 (13)
O4—H4	0.8668	C12—H12	0.9300
O5—C14	1.352 (10)	C13—C14	1.373 (12)
O5—H5	0.8200	C13—H13	0.9300
C1—C2	1.481 (9)	C15—H15A	0.9600
C2—C7	1.391 (10)	C15—H15B	0.9600
C2—C3	1.400 (9)	C15—H15C	0.9600
C3—C4	1.395 (10)	C16—H16A	0.9600
C3—H3A	0.9300	C16—H16B	0.9599
C4—C5	1.405 (10)	C16—H16C	0.9601
C4—H4A	0.9300
O1—Cd1—O1i	180.000 (1)	C5—C6—C7	120.7 (7)
O1—Cd1—O4i	90.19 (17)	C5—C6—H6	119.6
O1i—Cd1—O4i	89.81 (17)	C7—C6—H6	119.6
O1—Cd1—O4	89.81 (17)	C6—C7—C2	121.7 (7)
O1i—Cd1—O4	90.19 (17)	C6—C7—H7	119.1
O4i—Cd1—O4	180.000 (1)	C2—C7—H7	119.1
O1—Cd1—O3i	90.3 (2)	N1—C8—C9	121.4 (8)
O1i—Cd1—O3i	89.7 (2)	N1—C8—H8	119.3
O4i—Cd1—O3i	87.23 (19)	C9—C8—H8	119.3
O4—Cd1—O3i	92.77 (19)	C10—C9—C14	118.4 (8)
O1—Cd1—O3	89.7 (2)	C10—C9—C8	119.1 (8)
O1i—Cd1—O3	90.3 (2)	C14—C9—C8	122.5 (8)
O4i—Cd1—O3	92.77 (19)	C9—C10—C11	121.3 (9)
O4—Cd1—O3	87.23 (19)	C9—C10—H10	119.4
O3i—Cd1—O3	180.000 (1)	C11—C10—H10	119.4
C8—N1—C5	121.8 (7)	C12—C11—C10	118.9 (9)
C1—O1—Cd1	128.8 (5)	C12—C11—H11	120.5
C15—O3—Cd1	122.5 (4)	C10—C11—H11	120.5
C15—O3—H3	109.5	C11—C12—C13	122.4 (9)
Cd1—O3—H3	115.5	C11—C12—H12	118.8
C16—O4—Cd1	128.8 (4)	C13—C12—H12	118.8
C16—O4—H4	110.1	C14—C13—C12	117.7 (9)
Cd1—O4—H4	107.7	C14—C13—H13	121.1
C14—O5—H5	109.5	C12—C13—H13	121.1
O1—C1—O2	124.0 (7)	O5—C14—C13	118.4 (9)
O1—C1—C2	117.3 (7)	O5—C14—C9	120.5 (7)
O2—C1—C2	118.7 (6)	C13—C14—C9	121.0 (8)
C7—C2—C3	117.3 (7)	O3—C15—H15A	109.5
C7—C2—C1	120.3 (6)	O3—C15—H15B	109.5
C3—C2—C1	122.3 (7)	H15A—C15—H15B	109.5
C4—C3—C2	121.6 (7)	O3—C15—H15C	109.5
C4—C3—H3A	119.2	H15A—C15—H15C	109.5
C2—C3—H3A	119.2	H15B—C15—H15C	109.5
C3—C4—C5	119.4 (7)	O4—C16—H16A	110.1
C3—C4—H4A	120.3	O4—C16—H16B	109.4
C5—C4—H4A	120.3	H16A—C16—H16B	109.5
C6—C5—C4	119.1 (7)	O4—C16—H16C	108.9
C6—C5—N1	116.9 (7)	H16A—C16—H16C	109.5
C4—C5—N1	124.0 (7)	H16B—C16—H16C	109.5
O4i—Cd1—O1—C1	−171.4 (7)	C3—C4—C5—N1	−178.4 (7)
O4—Cd1—O1—C1	8.6 (7)	C8—N1—C5—C6	157.7 (8)
O3i—Cd1—O1—C1	−84.2 (7)	C8—N1—C5—C4	−24.4 (12)
O3—Cd1—O1—C1	95.8 (7)	C4—C5—C6—C7	0.2 (12)
O1—Cd1—O3—C15	−47.5 (5)	N1—C5—C6—C7	178.2 (7)
O1i—Cd1—O3—C15	132.5 (5)	C5—C6—C7—C2	0.8 (13)
O4i—Cd1—O3—C15	−137.7 (5)	C3—C2—C7—C6	−1.3 (12)
O4—Cd1—O3—C15	42.3 (5)	C1—C2—C7—C6	−179.8 (7)
O1—Cd1—O4—C16	−140.8 (6)	C5—N1—C8—C9	174.8 (7)
O1i—Cd1—O4—C16	39.2 (6)	N1—C8—C9—C10	−175.5 (8)
O3i—Cd1—O4—C16	−50.5 (6)	N1—C8—C9—C14	3.0 (13)
O3—Cd1—O4—C16	129.5 (6)	C14—C9—C10—C11	−2.9 (13)
Cd1—O1—C1—O2	−2.5 (12)	C8—C9—C10—C11	175.6 (8)
Cd1—O1—C1—C2	178.8 (5)	C9—C10—C11—C12	4.0 (15)
O1—C1—C2—C7	6.8 (11)	C10—C11—C12—C13	−4.0 (16)
O2—C1—C2—C7	−171.9 (8)	C11—C12—C13—C14	3.0 (15)
O1—C1—C2—C3	−171.6 (7)	C12—C13—C14—O5	178.3 (8)
O2—C1—C2—C3	9.7 (11)	C12—C13—C14—C9	−1.9 (14)
C7—C2—C3—C4	1.0 (12)	C10—C9—C14—O5	−178.3 (8)
C1—C2—C3—C4	179.4 (7)	C8—C9—C14—O5	3.2 (13)
C2—C3—C4—C5	−0.1 (13)	C10—C9—C14—C13	1.9 (13)
C3—C4—C5—C6	−0.5 (12)	C8—C9—C14—C13	−176.6 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2	0.87	1.87	2.653 (7)	150
O5—H5···N1	0.82	1.90	2.632 (9)	148
O3—H3···O2ii	0.85	1.83	2.640 (7)	160

Table 1

Selected bond lengths (Å)

Cd1—O1	2.230 (5)
Cd1—O4	2.295 (5)
Cd1—O3	2.315 (5)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O2	0.87	1.87	2.653 (7)	150
O5—H5⋯N1	0.82	1.90	2.632 (9)	148
O3—H3⋯O2i	0.85	1.83	2.640 (7)	160

Symmetry code: (i) .