{6,6'-Dimethoxy-2,2'-[cyclo-hexane-1,2-diylbis(nitrilo-methyl-idyne)]diphenolato-κO,N,N',O}iron(II) monohydrate.

In the title complex, [Fe(C(22)H(24)N(2)O(4))]·H(2)O, the Fe(II) center is four-coordinated by two O and two N atoms from 2,2'-[6,6'-dimethoxy-cyclo-hexane-1,2-diylbis(nitrilo-methyl-idyne)]diphen-olate (L) ligands in a distorted square-planar geometry. Uncoordinated water and FeL mol-ecules are paired via inter-molecular water-meth-oxy O-H⋯O hydrogen bonds.

Related literature

For a manganese complex of a similar Schiff base ligand, see: Watkinson et al. (1999 ▶). For the isotypic CoII compound, see: Bao et al. (2009 ▶).

Experimental

Crystal data

[Fe(C22H24N2O4)]·H2O

M = 454.30

Monoclinic,

a = 11.243 (5) Å

b = 10.617 (3) Å

c = 17.863 (7) Å

β = 107.042 (14)°

V = 2038.5 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.78 mm−1

T = 291 K

0.22 × 0.21 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.846, T max = 0.873

18680 measured reflections

4584 independent reflections

3446 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.107

S = 1.03

4584 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.30 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022235/cv2567sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022235/cv2567Isup2.hkl

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

[Fe(C22H24N2O4)]·H2O	F(000) = 952
Mr = 454.30	Dx = 1.480 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 13436 reflections
a = 11.243 (5) Å	θ = 3.1–27.5°
b = 10.617 (3) Å	µ = 0.78 mm−1
c = 17.863 (7) Å	T = 291 K
β = 107.042 (14)°	Block, black
V = 2038.5 (13) Å3	0.22 × 0.21 × 0.18 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	4584 independent reflections
Radiation source: fine-focus sealed tube	3446 reflections with I > 2σ(I)
graphite	Rint = 0.054
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
Tmin = 0.846, Tmax = 0.873	k = −13→13
18680 measured reflections	l = −23→23

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0436P)2 + 1.092P] where P = (Fo2 + 2Fc2)/3
4584 reflections	(Δ/σ)max = 0.001
273 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.35 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
Fe1	0.65626 (3)	0.46981 (3)	0.162776 (18)	0.02766 (11)
N1	0.7304 (2)	0.52432 (19)	0.08782 (12)	0.0356 (5)
O1	0.55829 (18)	0.34802 (16)	0.09933 (10)	0.0414 (4)
O3	0.57113 (19)	0.43064 (17)	0.23484 (11)	0.0447 (5)
N2	0.7650 (2)	0.5782 (2)	0.23003 (12)	0.0397 (5)
C7	0.6991 (3)	0.4904 (2)	0.01541 (15)	0.0385 (6)
H7	0.7339	0.5350	−0.0178	0.046*
C1	0.5517 (2)	0.3230 (2)	0.02601 (15)	0.0370 (6)
C2	0.4762 (3)	0.2205 (3)	−0.01171 (17)	0.0439 (6)
C20	0.5684 (3)	0.5024 (2)	0.29420 (15)	0.0401 (6)
O4	0.3917 (2)	0.3866 (2)	0.29798 (13)	0.0597 (6)
C19	0.4729 (3)	0.4826 (3)	0.33048 (17)	0.0481 (7)
O2	0.4206 (2)	0.1564 (2)	0.03582 (13)	0.0636 (6)
C8	0.8176 (3)	0.6325 (2)	0.11520 (15)	0.0394 (6)
H8	0.7676	0.7097	0.1075	0.047*
C14	0.7552 (3)	0.6262 (2)	0.29455 (15)	0.0414 (6)
H14	0.8169	0.6814	0.3220	0.050*
C6	0.6156 (2)	0.3903 (2)	−0.01837 (15)	0.0372 (6)
C4	0.5227 (3)	0.2627 (3)	−0.13222 (17)	0.0517 (7)
H4	0.5117	0.2439	−0.1847	0.062*
C15	0.6547 (3)	0.5989 (3)	0.32603 (15)	0.0421 (6)
C5	0.5980 (3)	0.3603 (3)	−0.09773 (16)	0.0464 (7)
H5	0.6381	0.4075	−0.1269	0.056*
C13	0.8726 (3)	0.6129 (2)	0.20281 (16)	0.0411 (6)
H13	0.9091	0.6918	0.2277	0.049*
C12	0.9700 (3)	0.5089 (3)	0.22201 (18)	0.0502 (7)
H12A	0.9306	0.4287	0.2040	0.060*
H12B	1.0067	0.5038	0.2783	0.060*
C3	0.4622 (3)	0.1911 (3)	−0.08882 (17)	0.0495 (7)
H3	0.4125	0.1234	−0.1121	0.059*
C9	0.9182 (3)	0.6509 (3)	0.07480 (17)	0.0486 (7)
H9A	0.8798	0.6520	0.0186	0.058*
H9B	0.9578	0.7319	0.0899	0.058*
C10	1.0165 (3)	0.5485 (3)	0.09490 (19)	0.0594 (8)
H10A	1.0822	0.5690	0.0719	0.071*
H10B	0.9797	0.4692	0.0727	0.071*
C11	1.0719 (3)	0.5339 (4)	0.1833 (2)	0.0648 (9)
H11A	1.1307	0.4646	0.1943	0.078*
H11B	1.1165	0.6101	0.2049	0.078*
C18	0.4656 (3)	0.5554 (3)	0.3928 (2)	0.0633 (9)
H18	0.4018	0.5412	0.4152	0.076*
C21	0.2942 (3)	0.3601 (4)	0.3316 (2)	0.0694 (10)
H21A	0.3291	0.3303	0.3843	0.104*
H21B	0.2405	0.2967	0.3012	0.104*
H21C	0.2472	0.4354	0.3322	0.104*
C17	0.5525 (4)	0.6499 (3)	0.4229 (2)	0.0674 (10)
H17	0.5468	0.6982	0.4651	0.081*
C16	0.6452 (3)	0.6712 (3)	0.39035 (18)	0.0551 (8)
H16	0.7032	0.7342	0.4106	0.066*
O5	0.3096 (3)	0.3010 (3)	0.13694 (18)	0.1061 (11)
H1	0.3424	0.3299	0.1827	0.159*
H2	0.3649	0.2594	0.1238	0.159*
C22	0.3307 (3)	0.0621 (3)	0.0015 (2)	0.0666 (10)
H22A	0.2609	0.1004	−0.0360	0.100*
H22B	0.3032	0.0219	0.0416	0.100*
H22C	0.3674	0.0005	−0.0243	0.100*

	U11	U22	U33	U12	U13	U23
Fe1	0.02801 (19)	0.03099 (18)	0.02628 (18)	−0.00228 (14)	0.01153 (13)	−0.00086 (13)
N1	0.0334 (12)	0.0387 (11)	0.0353 (11)	−0.0007 (9)	0.0108 (9)	0.0018 (9)
O1	0.0425 (11)	0.0466 (10)	0.0377 (10)	−0.0046 (8)	0.0157 (8)	−0.0025 (7)
O3	0.0515 (12)	0.0491 (10)	0.0391 (10)	−0.0053 (9)	0.0221 (9)	−0.0030 (8)
N2	0.0406 (13)	0.0432 (12)	0.0382 (12)	−0.0011 (10)	0.0163 (10)	−0.0013 (9)
C7	0.0384 (15)	0.0438 (14)	0.0351 (14)	0.0024 (11)	0.0136 (12)	0.0046 (10)
C1	0.0351 (15)	0.0369 (13)	0.0386 (14)	0.0047 (10)	0.0101 (12)	−0.0025 (10)
C2	0.0398 (16)	0.0464 (15)	0.0470 (16)	0.0015 (12)	0.0148 (13)	−0.0043 (12)
C20	0.0409 (16)	0.0498 (15)	0.0318 (13)	0.0055 (11)	0.0141 (12)	0.0041 (10)
O4	0.0513 (14)	0.0833 (15)	0.0531 (13)	−0.0119 (11)	0.0289 (11)	0.0000 (11)
C19	0.0444 (18)	0.0620 (18)	0.0408 (16)	0.0010 (14)	0.0169 (13)	0.0047 (13)
O2	0.0712 (16)	0.0618 (13)	0.0629 (14)	−0.0281 (11)	0.0277 (12)	−0.0130 (10)
C8	0.0363 (15)	0.0393 (14)	0.0432 (15)	−0.0015 (11)	0.0129 (12)	0.0038 (11)
C14	0.0414 (16)	0.0463 (15)	0.0359 (14)	0.0002 (12)	0.0101 (12)	−0.0035 (11)
C6	0.0342 (14)	0.0418 (14)	0.0349 (13)	0.0054 (11)	0.0086 (11)	−0.0004 (10)
C4	0.0539 (19)	0.0608 (18)	0.0390 (16)	0.0104 (14)	0.0112 (14)	−0.0096 (13)
C15	0.0470 (17)	0.0469 (15)	0.0340 (14)	0.0011 (12)	0.0143 (12)	−0.0002 (11)
C5	0.0456 (18)	0.0559 (17)	0.0383 (15)	0.0046 (13)	0.0134 (13)	−0.0003 (12)
C13	0.0387 (16)	0.0445 (14)	0.0417 (15)	−0.0055 (11)	0.0143 (12)	−0.0025 (11)
C12	0.0397 (17)	0.0653 (19)	0.0439 (16)	0.0075 (13)	0.0098 (13)	0.0074 (13)
C3	0.0473 (18)	0.0480 (16)	0.0498 (17)	0.0019 (13)	0.0086 (14)	−0.0111 (13)
C9	0.0451 (18)	0.0587 (18)	0.0440 (16)	−0.0118 (13)	0.0162 (14)	0.0028 (12)
C10	0.0436 (19)	0.085 (2)	0.056 (2)	0.0016 (16)	0.0244 (16)	0.0000 (16)
C11	0.0369 (18)	0.098 (3)	0.061 (2)	0.0095 (17)	0.0161 (15)	0.0101 (18)
C18	0.057 (2)	0.093 (3)	0.0510 (19)	0.0029 (18)	0.0322 (17)	−0.0024 (16)
C21	0.046 (2)	0.106 (3)	0.065 (2)	−0.0016 (19)	0.0290 (17)	0.0186 (19)
C17	0.077 (3)	0.084 (2)	0.051 (2)	−0.001 (2)	0.0337 (19)	−0.0176 (17)
C16	0.062 (2)	0.0628 (19)	0.0436 (17)	0.0018 (15)	0.0206 (15)	−0.0097 (13)
O5	0.080 (2)	0.167 (3)	0.080 (2)	−0.021 (2)	0.0366 (17)	−0.0236 (19)
C22	0.055 (2)	0.0543 (19)	0.085 (3)	−0.0180 (15)	0.0124 (19)	−0.0009 (16)

Fe1—N2	1.844 (2)	C4—H4	0.9300
Fe1—O1	1.8541 (18)	C15—C16	1.412 (4)
Fe1—O3	1.8623 (19)	C5—H5	0.9300
Fe1—N1	1.864 (2)	C13—C12	1.523 (4)
N1—C7	1.288 (3)	C13—H13	0.9800
N1—C8	1.496 (3)	C12—C11	1.525 (4)
O1—C1	1.317 (3)	C12—H12A	0.9700
O3—C20	1.313 (3)	C12—H12B	0.9700
N2—C14	1.294 (3)	C3—H3	0.9300
N2—C13	1.476 (3)	C9—C10	1.517 (4)
C7—C6	1.429 (4)	C9—H9A	0.9700
C7—H7	0.9300	C9—H9B	0.9700
C1—C6	1.410 (4)	C10—C11	1.525 (5)
C1—C2	1.423 (4)	C10—H10A	0.9700
C2—O2	1.373 (3)	C10—H10B	0.9700
C2—C3	1.376 (4)	C11—H11A	0.9700
C20—C15	1.411 (4)	C11—H11B	0.9700
C20—C19	1.424 (4)	C18—C17	1.394 (5)
O4—C19	1.378 (4)	C18—H18	0.9300
O4—C21	1.425 (4)	C21—H21A	0.9600
C19—C18	1.377 (4)	C21—H21B	0.9600
O2—C22	1.428 (4)	C21—H21C	0.9600
C8—C13	1.519 (4)	C17—C16	1.352 (5)
C8—C9	1.522 (4)	C17—H17	0.9300
C8—H8	0.9800	C16—H16	0.9300
C14—C15	1.431 (4)	O5—H1	0.8500
C14—H14	0.9300	O5—H2	0.8500
C6—C5	1.409 (4)	C22—H22A	0.9600
C4—C5	1.365 (4)	C22—H22B	0.9600
C4—C3	1.397 (4)	C22—H22C	0.9600
N2—Fe1—O1	174.23 (9)	C8—C13—C12	112.4 (2)
N2—Fe1—O3	93.78 (9)	N2—C13—H13	109.8
O1—Fe1—O3	86.17 (8)	C8—C13—H13	109.8
N2—Fe1—N1	85.62 (10)	C12—C13—H13	109.8
O1—Fe1—N1	95.05 (9)	C13—C12—C11	111.0 (2)
O3—Fe1—N1	173.78 (9)	C13—C12—H12A	109.4
C7—N1—C8	120.2 (2)	C11—C12—H12A	109.4
C7—N1—Fe1	125.91 (19)	C13—C12—H12B	109.4
C8—N1—Fe1	113.05 (16)	C11—C12—H12B	109.4
C1—O1—Fe1	126.75 (17)	H12A—C12—H12B	108.0
C20—O3—Fe1	124.53 (17)	C2—C3—C4	120.0 (3)
C14—N2—C13	119.1 (2)	C2—C3—H3	120.0
C14—N2—Fe1	127.8 (2)	C4—C3—H3	120.0
C13—N2—Fe1	113.07 (16)	C10—C9—C8	112.8 (2)
N1—C7—C6	125.7 (2)	C10—C9—H9A	109.0
N1—C7—H7	117.1	C8—C9—H9A	109.0
C6—C7—H7	117.1	C10—C9—H9B	109.0
O1—C1—C6	124.6 (2)	C8—C9—H9B	109.0
O1—C1—C2	118.5 (2)	H9A—C9—H9B	107.8
C6—C1—C2	116.9 (2)	C9—C10—C11	111.5 (3)
O2—C2—C3	124.5 (3)	C9—C10—H10A	109.3
O2—C2—C1	113.8 (2)	C11—C10—H10A	109.3
C3—C2—C1	121.7 (3)	C9—C10—H10B	109.3
O3—C20—C15	124.8 (3)	C11—C10—H10B	109.3
O3—C20—C19	118.8 (3)	H10A—C10—H10B	108.0
C15—C20—C19	116.4 (2)	C12—C11—C10	110.7 (3)
C19—O4—C21	117.7 (3)	C12—C11—H11A	109.5
C18—C19—O4	124.5 (3)	C10—C11—H11A	109.5
C18—C19—C20	121.2 (3)	C12—C11—H11B	109.5
O4—C19—C20	114.3 (2)	C10—C11—H11B	109.5
C2—O2—C22	118.4 (3)	H11A—C11—H11B	108.1
N1—C8—C13	105.1 (2)	C19—C18—C17	120.9 (3)
N1—C8—C9	116.7 (2)	C19—C18—H18	119.6
C13—C8—C9	111.8 (2)	C17—C18—H18	119.6
N1—C8—H8	107.6	O4—C21—H21A	109.5
C13—C8—H8	107.6	O4—C21—H21B	109.5
C9—C8—H8	107.6	H21A—C21—H21B	109.5
N2—C14—C15	123.6 (3)	O4—C21—H21C	109.5
N2—C14—H14	118.2	H21A—C21—H21C	109.5
C15—C14—H14	118.2	H21B—C21—H21C	109.5
C5—C6—C1	120.4 (2)	C16—C17—C18	119.8 (3)
C5—C6—C7	118.3 (2)	C16—C17—H17	120.1
C1—C6—C7	121.3 (2)	C18—C17—H17	120.1
C5—C4—C3	120.1 (3)	C17—C16—C15	120.7 (3)
C5—C4—H4	120.0	C17—C16—H16	119.6
C3—C4—H4	120.0	C15—C16—H16	119.6
C20—C15—C16	121.0 (3)	H1—O5—H2	107.8
C20—C15—C14	121.1 (2)	O2—C22—H22A	109.5
C16—C15—C14	117.8 (3)	O2—C22—H22B	109.5
C4—C5—C6	120.8 (3)	H22A—C22—H22B	109.5
C4—C5—H5	119.6	O2—C22—H22C	109.5
C6—C5—H5	119.6	H22A—C22—H22C	109.5
N2—C13—C8	104.4 (2)	H22B—C22—H22C	109.5
N2—C13—C12	110.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H2···O1	0.85	2.52	3.102 (4)	126
O5—H2···O2	0.85	2.15	2.915 (4)	149
O5—H1···O3	0.85	2.69	3.254 (4)	125
O5—H1···O4	0.85	2.06	2.898 (4)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H2⋯O2	0.85	2.15	2.915 (4)	149
O5—H1⋯O4	0.85	2.06	2.898 (4)	169