Aqua-(cyanido-κC){6,6'-dimeth-oxy-2,2'-[o-phenyl-enebis(nitrilo-methanylyl-idene)]diphenolato-κO,N,N',O}cobalt(III) acetonitrile monosolvate.

In the title complex, [Co(C(22)H(18)N(2)O(4))(CN)(H(2)O)]·CH(3)CN, the Co(III) ion is six-coordinated in a distorted octa-hedral environment defined by two N atoms and two O atoms from a salen ligand in the equatorial plane and one O atom from a water mol-ecule and one C atom from a cyanide group at the axial positions. O-H⋯O hydrogen bonds connect adjacent complex mol-ecules into dimers. C-H⋯N hydrogen bonds and π-π inter-actions between the benzene rings [centroid-centroid distances = 3.700 (2) and 3.845 (2) Å] are also present.

Related literature

For the synthesis of the ligand, see: Costes et al. (2000 ▶). For related transition-metal complexes, see: Przychodzeń et al. (2005 ▶). For bond-valence calculations, see: Spek (2009 ▶).

Experimental

Crystal data

[Co(C22H18N2O4)(CN)(H2O)]·C2H3N

M = 518.40

Monoclinic,

a = 10.829 (2) Å

b = 13.209 (3) Å

c = 18.906 (6) Å

β = 118.30 (2)°

V = 2381.1 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.77 mm−1

T = 293 K

0.34 × 0.31 × 0.29 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.780, T max = 0.811

22543 measured reflections

5426 independent reflections

4439 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.096

S = 1.08

5426 reflections

319 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.35 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811029461/hy2451sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029461/hy2451Isup2.hkl

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

[Co(C22H18N2O4)(CN)(H2O)]·C2H3N	F(000) = 1072
Mr = 518.40	Dx = 1.446 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 17687 reflections
a = 10.829 (2) Å	θ = 3.1–27.5°
b = 13.209 (3) Å	µ = 0.77 mm−1
c = 18.906 (6) Å	T = 293 K
β = 118.30 (2)°	Block, brown
V = 2381.1 (10) Å3	0.34 × 0.31 × 0.29 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	5426 independent reflections
Radiation source: fine-focus sealed tube	4439 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→14
Tmin = 0.780, Tmax = 0.811	k = −17→17
22543 measured reflections	l = −24→24

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.046P)2 + 0.9325P] where P = (Fo2 + 2Fc2)/3
5426 reflections	(Δ/σ)max = 0.001
319 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.5547 (3)	0.1426 (2)	−0.19502 (14)	0.0647 (8)
H1A	0.5301	0.0812	−0.2259	0.097*
H1B	0.5808	0.1932	−0.2219	0.097*
H1C	0.4757	0.1661	−0.1896	0.097*
C2	0.7165 (2)	0.20216 (16)	−0.06373 (12)	0.0371 (4)
C3	0.6721 (2)	0.30104 (17)	−0.08039 (14)	0.0469 (5)
H3	0.6029	0.3184	−0.1317	0.056*
C4	0.7297 (3)	0.37577 (17)	−0.02117 (15)	0.0504 (6)
H4	0.6997	0.4425	−0.0334	0.060*
C5	0.8296 (2)	0.35112 (16)	0.05426 (14)	0.0441 (5)
H5	0.8671	0.4012	0.0934	0.053*
C6	0.8773 (2)	0.24945 (14)	0.07391 (12)	0.0341 (4)
C7	0.8218 (2)	0.17321 (14)	0.01489 (11)	0.0312 (4)
C8	0.9842 (2)	0.22983 (15)	0.15339 (12)	0.0333 (4)
H8	1.0159	0.2846	0.1885	0.040*
C9	1.1540 (2)	0.13197 (15)	0.26124 (11)	0.0318 (4)
C10	1.2143 (2)	0.21081 (16)	0.31618 (12)	0.0405 (5)
H10	1.1825	0.2769	0.3018	0.049*
C11	1.3210 (2)	0.18993 (18)	0.39164 (13)	0.0469 (5)
H11	1.3610	0.2422	0.4286	0.056*
C12	1.3696 (2)	0.09200 (19)	0.41328 (13)	0.0466 (5)
H12	1.4418	0.0790	0.4647	0.056*
C13	1.3121 (2)	0.01354 (17)	0.35951 (12)	0.0401 (5)
H13	1.3456	−0.0521	0.3743	0.048*
C14	1.2030 (2)	0.03317 (14)	0.28252 (11)	0.0316 (4)
C15	1.1581 (2)	−0.13640 (15)	0.23320 (11)	0.0323 (4)
H15	1.2264	−0.1561	0.2841	0.039*
C16	0.9948 (2)	−0.19407 (14)	0.09435 (11)	0.0300 (4)
C17	1.0922 (2)	−0.21447 (14)	0.17560 (11)	0.0324 (4)
C18	1.1305 (2)	−0.31644 (15)	0.20116 (13)	0.0397 (5)
H18	1.1953	−0.3296	0.2544	0.048*
C19	1.0737 (3)	−0.39453 (16)	0.14897 (14)	0.0455 (5)
H19	1.0989	−0.4608	0.1666	0.055*
C20	0.9769 (2)	−0.37543 (15)	0.06817 (13)	0.0419 (5)
H20	0.9385	−0.4292	0.0326	0.050*
C21	0.9386 (2)	−0.27817 (15)	0.04140 (12)	0.0345 (4)
C22	0.7825 (3)	−0.32967 (19)	−0.09336 (14)	0.0562 (7)
H22A	0.7288	−0.3007	−0.1458	0.084*
H22B	0.7218	−0.3684	−0.0797	0.084*
H22C	0.8537	−0.3731	−0.0932	0.084*
C23	0.8551 (2)	−0.00903 (15)	0.15346 (12)	0.0348 (4)
Co1	0.99408 (3)	0.018833 (18)	0.124299 (14)	0.02757 (9)
N1	1.04207 (17)	0.14260 (11)	0.18179 (9)	0.0293 (3)
N2	1.13171 (17)	−0.03998 (12)	0.22136 (9)	0.0296 (3)
N4	0.7711 (2)	−0.02985 (16)	0.17105 (14)	0.0538 (5)
O1	0.95350 (15)	−0.10306 (10)	0.06457 (7)	0.0332 (3)
O2	0.86109 (14)	0.07822 (10)	0.02591 (8)	0.0343 (3)
O3	0.84670 (17)	−0.25085 (11)	−0.03599 (8)	0.0434 (4)
O4	0.66969 (16)	0.12382 (12)	−0.11736 (9)	0.0465 (4)
O5	1.14913 (14)	0.04801 (10)	0.09656 (8)	0.0339 (3)
H51	1.1136	0.0809	0.0527	0.051*
H52	1.1992	0.0032	0.0901	0.051*
N3	1.4525 (3)	−0.2365 (3)	0.39165 (18)	0.1011 (11)
C24	1.4969 (3)	−0.3138 (3)	0.41113 (18)	0.0685 (8)
C25	1.5580 (4)	−0.4129 (3)	0.4384 (3)	0.1254 (18)
H25A	1.6559	−0.4058	0.4759	0.188*
H25B	1.5474	−0.4524	0.3933	0.188*
H25C	1.5113	−0.4461	0.4643	0.188*

	U11	U22	U33	U12	U13	U23
C1	0.0577 (16)	0.0727 (19)	0.0373 (12)	0.0148 (13)	0.0009 (11)	0.0020 (12)
C2	0.0379 (11)	0.0340 (10)	0.0368 (10)	0.0067 (8)	0.0156 (9)	0.0031 (9)
C3	0.0467 (13)	0.0404 (12)	0.0450 (12)	0.0148 (10)	0.0148 (10)	0.0137 (10)
C4	0.0585 (14)	0.0275 (10)	0.0612 (14)	0.0144 (10)	0.0251 (12)	0.0115 (11)
C5	0.0518 (13)	0.0264 (10)	0.0522 (13)	0.0078 (9)	0.0231 (11)	0.0017 (10)
C6	0.0374 (10)	0.0254 (9)	0.0409 (10)	0.0058 (8)	0.0197 (9)	0.0021 (8)
C7	0.0333 (10)	0.0283 (9)	0.0353 (10)	0.0063 (7)	0.0191 (8)	0.0039 (8)
C8	0.0424 (11)	0.0246 (9)	0.0371 (10)	0.0006 (8)	0.0221 (9)	−0.0045 (8)
C9	0.0343 (10)	0.0296 (10)	0.0297 (9)	−0.0027 (8)	0.0137 (8)	−0.0032 (8)
C10	0.0450 (12)	0.0314 (10)	0.0392 (11)	−0.0020 (9)	0.0152 (9)	−0.0068 (9)
C11	0.0490 (13)	0.0429 (13)	0.0393 (11)	−0.0096 (10)	0.0132 (10)	−0.0138 (10)
C12	0.0419 (12)	0.0524 (14)	0.0317 (10)	−0.0052 (10)	0.0063 (9)	−0.0039 (10)
C13	0.0396 (11)	0.0374 (11)	0.0342 (10)	−0.0005 (9)	0.0101 (9)	0.0020 (9)
C14	0.0340 (10)	0.0298 (10)	0.0297 (9)	−0.0024 (7)	0.0142 (8)	−0.0015 (8)
C15	0.0366 (10)	0.0300 (10)	0.0286 (9)	0.0033 (8)	0.0142 (8)	0.0044 (8)
C16	0.0376 (10)	0.0213 (8)	0.0336 (9)	0.0009 (7)	0.0190 (8)	0.0002 (8)
C17	0.0391 (11)	0.0245 (9)	0.0338 (9)	0.0024 (8)	0.0176 (8)	0.0027 (8)
C18	0.0493 (12)	0.0290 (10)	0.0386 (11)	0.0070 (9)	0.0192 (10)	0.0072 (9)
C19	0.0622 (15)	0.0221 (10)	0.0511 (13)	0.0055 (9)	0.0261 (11)	0.0056 (9)
C20	0.0582 (14)	0.0241 (10)	0.0439 (11)	−0.0022 (9)	0.0246 (10)	−0.0056 (9)
C21	0.0416 (11)	0.0273 (10)	0.0340 (10)	−0.0020 (8)	0.0175 (9)	−0.0022 (8)
C22	0.0664 (16)	0.0424 (13)	0.0420 (12)	−0.0086 (12)	0.0110 (12)	−0.0140 (11)
C23	0.0384 (11)	0.0269 (9)	0.0352 (10)	−0.0009 (8)	0.0143 (9)	−0.0044 (8)
Co1	0.03420 (15)	0.02039 (13)	0.02460 (13)	0.00213 (10)	0.01105 (10)	−0.00039 (10)
N1	0.0368 (9)	0.0240 (8)	0.0277 (7)	0.0003 (6)	0.0158 (7)	−0.0023 (6)
N2	0.0343 (8)	0.0262 (8)	0.0264 (7)	0.0000 (6)	0.0130 (6)	−0.0009 (6)
N4	0.0546 (12)	0.0493 (12)	0.0678 (14)	−0.0096 (10)	0.0373 (11)	−0.0099 (10)
O1	0.0463 (8)	0.0212 (6)	0.0261 (6)	0.0023 (5)	0.0123 (6)	−0.0006 (5)
O2	0.0420 (8)	0.0260 (7)	0.0286 (6)	0.0069 (6)	0.0116 (6)	0.0004 (5)
O3	0.0547 (9)	0.0283 (7)	0.0341 (7)	−0.0033 (6)	0.0104 (7)	−0.0058 (6)
O4	0.0471 (9)	0.0422 (9)	0.0346 (8)	0.0103 (7)	0.0067 (7)	0.0018 (7)
O5	0.0400 (7)	0.0303 (7)	0.0324 (7)	0.0050 (6)	0.0180 (6)	0.0024 (6)
N3	0.087 (2)	0.088 (2)	0.088 (2)	0.0309 (18)	0.0079 (17)	0.0136 (18)
C24	0.0522 (16)	0.073 (2)	0.0594 (16)	0.0092 (14)	0.0092 (13)	−0.0069 (15)
C25	0.083 (3)	0.059 (2)	0.185 (5)	0.0098 (19)	0.023 (3)	−0.001 (3)

C1—O4	1.426 (3)	C15—C17	1.422 (3)
C1—H1A	0.9600	C15—H15	0.9300
C1—H1B	0.9600	C16—O1	1.313 (2)
C1—H1C	0.9600	C16—C17	1.417 (3)
C2—O4	1.367 (3)	C16—C21	1.424 (3)
C2—C3	1.376 (3)	C17—C18	1.425 (3)
C2—C7	1.431 (3)	C18—C19	1.357 (3)
C3—C4	1.398 (3)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.406 (3)
C4—C5	1.359 (3)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.371 (3)
C5—C6	1.424 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—O3	1.372 (2)
C6—C7	1.409 (3)	C22—O3	1.424 (3)
C6—C8	1.420 (3)	C22—H22A	0.9600
C7—O2	1.309 (2)	C22—H22B	0.9600
C8—N1	1.300 (2)	C22—H22C	0.9600
C8—H8	0.9300	C23—N4	1.140 (3)
C9—C14	1.394 (3)	Co1—C23	1.869 (2)
C9—C10	1.395 (3)	Co1—N1	1.8944 (15)
C9—N1	1.421 (2)	Co1—N2	1.8972 (16)
C10—C11	1.372 (3)	Co1—O1	1.8948 (13)
C10—H10	0.9300	Co1—O2	1.8998 (14)
C11—C12	1.383 (3)	Co1—O5	2.0194 (14)
C11—H11	0.9300	O5—H51	0.8500
C12—C13	1.377 (3)	O5—H52	0.8500
C12—H12	0.9300	N3—C24	1.114 (4)
C13—C14	1.397 (3)	C24—C25	1.447 (5)
C13—H13	0.9300	C25—H25A	0.9600
C14—N2	1.421 (2)	C25—H25B	0.9600
C15—N2	1.301 (2)	C25—H25C	0.9600
O4—C1—H1A	109.5	C19—C18—C17	120.90 (19)
O4—C1—H1B	109.5	C19—C18—H18	119.6
H1A—C1—H1B	109.5	C17—C18—H18	119.6
O4—C1—H1C	109.5	C18—C19—C20	120.06 (19)
H1A—C1—H1C	109.5	C18—C19—H19	120.0
H1B—C1—H1C	109.5	C20—C19—H19	120.0
O4—C2—C3	125.62 (19)	C21—C20—C19	120.55 (19)
O4—C2—C7	113.63 (17)	C21—C20—H20	119.7
C3—C2—C7	120.7 (2)	C19—C20—H20	119.7
C2—C3—C4	120.8 (2)	C20—C21—O3	125.44 (18)
C2—C3—H3	119.6	C20—C21—C16	121.19 (19)
C4—C3—H3	119.6	O3—C21—C16	113.37 (17)
C5—C4—C3	120.1 (2)	O3—C22—H22A	109.5
C5—C4—H4	119.9	O3—C22—H22B	109.5
C3—C4—H4	119.9	H22A—C22—H22B	109.5
C4—C5—C6	120.6 (2)	O3—C22—H22C	109.5
C4—C5—H5	119.7	H22A—C22—H22C	109.5
C6—C5—H5	119.7	H22B—C22—H22C	109.5
C7—C6—C8	122.36 (17)	N4—C23—Co1	177.41 (19)
C7—C6—C5	120.13 (19)	C23—Co1—N1	92.35 (8)
C8—C6—C5	117.48 (19)	C23—Co1—O1	90.96 (7)
O2—C7—C6	125.07 (17)	N1—Co1—O1	176.68 (7)
O2—C7—C2	117.38 (17)	C23—Co1—N2	90.42 (8)
C6—C7—C2	117.53 (17)	N1—Co1—N2	85.55 (7)
N1—C8—C6	126.20 (18)	O1—Co1—N2	94.73 (6)
N1—C8—H8	116.9	C23—Co1—O2	91.57 (8)
C6—C8—H8	116.9	N1—Co1—O2	94.58 (6)
C14—C9—C10	120.28 (18)	O1—Co1—O2	85.03 (6)
C14—C9—N1	114.50 (16)	N2—Co1—O2	178.00 (7)
C10—C9—N1	125.23 (18)	C23—Co1—O5	178.11 (7)
C11—C10—C9	119.3 (2)	N1—Co1—O5	87.05 (6)
C11—C10—H10	120.3	O1—Co1—O5	89.65 (6)
C9—C10—H10	120.3	N2—Co1—O5	87.75 (6)
C10—C11—C12	120.7 (2)	O2—Co1—O5	90.26 (6)
C10—C11—H11	119.7	C8—N1—C9	121.80 (16)
C12—C11—H11	119.7	C8—N1—Co1	125.49 (14)
C13—C12—C11	120.7 (2)	C9—N1—Co1	112.69 (12)
C13—C12—H12	119.7	C15—N2—C14	122.36 (16)
C11—C12—H12	119.7	C15—N2—Co1	125.09 (13)
C12—C13—C14	119.5 (2)	C14—N2—Co1	112.53 (12)
C12—C13—H13	120.2	C16—O1—Co1	125.94 (12)
C14—C13—H13	120.2	C7—O2—Co1	126.13 (12)
C9—C14—C13	119.50 (18)	C21—O3—C22	117.74 (17)
C9—C14—N2	114.59 (16)	C2—O4—C1	117.87 (19)
C13—C14—N2	125.90 (18)	Co1—O5—H51	107.7
N2—C15—C17	126.06 (18)	Co1—O5—H52	124.8
N2—C15—H15	117.0	H51—O5—H52	103.9
C17—C15—H15	117.0	N3—C24—C25	178.4 (4)
O1—C16—C17	124.47 (17)	C24—C25—H25A	109.5
O1—C16—C21	117.89 (17)	C24—C25—H25B	109.5
C17—C16—C21	117.64 (17)	H25A—C25—H25B	109.5
C16—C17—C15	122.53 (17)	C24—C25—H25C	109.5
C16—C17—C18	119.65 (18)	H25A—C25—H25C	109.5
C15—C17—C18	117.79 (18)	H25B—C25—H25C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O3i	0.85	2.33	2.922 (2)	127
O5—H51···O1i	0.85	2.00	2.799 (2)	156
O5—H52···O2i	0.85	2.24	2.813 (2)	124
O5—H52···O4i	0.85	2.10	2.902 (2)	158
C10—H10···N4ii	0.93	2.61	3.433 (3)	148
C15—H15···N3	0.93	2.56	3.440 (3)	159

Table 1

Selected bond lengths (Å)

Co1—C23	1.869 (2)
Co1—N1	1.8944 (15)
Co1—N2	1.8972 (16)
Co1—O1	1.8948 (13)
Co1—O2	1.8998 (14)
Co1—O5	2.0194 (14)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O3i	0.85	2.33	2.922 (2)	127
O5—H51⋯O1i	0.85	2.00	2.799 (2)	156
O5—H52⋯O2i	0.85	2.24	2.813 (2)	124
O5—H52⋯O4i	0.85	2.10	2.902 (2)	158
C10—H10⋯N4ii	0.93	2.61	3.433 (3)	148
C15—H15⋯N3	0.93	2.56	3.440 (3)	159

Symmetry codes: (i) ; (ii) .