trans-Bis­(iso­quinoline-3-carboxyl­ato-κ²N,O)bis­(methanol-κO)­iron(II)

The title complex, [Fe(C₁₀H₆NO₂)₂(CH₄O)₂], contains an Fe^II ion at a center of inversion. The Fe^II ion has a distorted octahedral coordination geometry, and is coordinated by two bidentate iso­quinoline-3-carboxyl­ate ligands through N and O atoms, and by two methanol O atoms. The two iso­quinoline-3-carboxyl­ate ligands lie in a trans position with respect to one another in the equatorial plane, and the two methanol ligands occupy the axial positions. The complex mol­ecules are linked together by hydrogen bonds between the methanol ligands and the carboxyl­ate groups.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.039
• wR factor = 0.141
• Data-to-parameter ratio = 16.1

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Computing details

Data collection: MSC/AFC (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC (Molecular Structure Corporation, 1992); data reduction: TEXSAN Version 1.11 (Molecular Structure Corporation & Rigaku, 2000); program(s) used to solve structure: SIR97 (Altomare et al., 1999) & DIRDIF94 (Beurskens et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN Version 1.11.

(I)

Crystal data

C22H20FeN2O6	F(000) = 480.0
Mr = 464.25	Dx = 1.538 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.798 (2) Å	θ = 13.2–14.4°
b = 6.281 (1) Å	µ = 0.80 mm^−1
c = 15.045 (2) Å	T = 296 K
β = 100.82 (1)°	Plate, dark orange
V = 1002.2 (3) Å^3	0.40 × 0.10 × 0.10 mm
Z = 2

Data collection

Rigaku AFC5R diffractometer	Rint = 0.024
ω–2θ scans	θmax = 27.5°
Absorption correction: ψ scan (North, Phillips & Mathews, 1968)	h = 0→14
Tmin = 0.909, Tmax = 0.923	k = 0→8
2641 measured reflections	l = −19→19
2301 independent reflections	3 standard reflections every 150 reflections
1433 reflections with I > 2.0σ(I)	intensity decay: 0.5%

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.141	(Δ/σ)max < 0.001
S = 0.86	Δρmax = 0.37 e Å^−3
2301 reflections	Δρmin = −0.36 e Å^−3
143 parameters

Special details

Refinement. Refinement using reflections with F² > -10.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Fe1	0.0000	0.0000	0.0000	0.0288 (2)
O1	0.0428 (2)	−0.2823 (3)	−0.0556 (2)	0.0336 (5)
O1M	−0.0396 (2)	−0.1720 (4)	0.1186 (2)	0.0370 (5)
O2	0.1961 (2)	−0.5171 (4)	−0.0622 (2)	0.0434 (6)
N1	0.2019 (2)	−0.0160 (4)	0.0482 (2)	0.0282 (5)
C1	0.2495 (3)	−0.2041 (5)	0.0225 (2)	0.0270 (6)
C2	0.3744 (3)	−0.2547 (5)	0.0457 (2)	0.0297 (6)
C3	0.4604 (3)	−0.1093 (5)	0.0957 (2)	0.0289 (6)
C4	0.5921 (3)	−0.1481 (6)	0.1193 (2)	0.0370 (7)
C5	0.6687 (3)	0.0038 (6)	0.1639 (2)	0.0419 (8)
C6	0.6201 (3)	0.1995 (6)	0.1888 (2)	0.0413 (8)
C7	0.4939 (3)	0.2388 (6)	0.1676 (2)	0.0363 (7)
C8	0.4114 (3)	0.0863 (5)	0.1206 (2)	0.0283 (6)
C9	0.2801 (3)	0.1214 (5)	0.0949 (2)	0.0301 (6)
C10	0.1550 (3)	−0.3482 (5)	−0.0364 (2)	0.0299 (6)
C11	0.0515 (4)	−0.2422 (8)	0.1936 (3)	0.058 (1)
H1M	−0.0954	−0.2926	0.1043	0.0536*
H2	0.4030	−0.3853	0.0285	0.0357*
H4	0.6254	−0.2768	0.1042	0.0444*
H5	0.7551	−0.0212	0.1785	0.0503*
H6	0.6742	0.3014	0.2196	0.0495*
H7	0.4621	0.3674	0.1843	0.0435*
H9	0.2473	0.2487	0.1120	0.0361*
H11A	0.0903	−0.3708	0.1778	0.0865*
H11B	0.0111	−0.2689	0.2442	0.0865*
H11C	0.1147	−0.1342	0.2095	0.0865*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0199 (3)	0.0264 (3)	0.0383 (3)	0.0036 (3)	0.0008 (2)	−0.0033 (3)
O1	0.025 (1)	0.029 (1)	0.044 (1)	0.0004 (9)	−0.0010 (9)	−0.0073 (10)
O1M	0.032 (1)	0.035 (1)	0.042 (1)	−0.0032 (10)	0.0008 (9)	0.002 (1)
O2	0.032 (1)	0.031 (1)	0.067 (2)	0.0011 (10)	0.009 (1)	−0.015 (1)
N1	0.022 (1)	0.027 (1)	0.034 (1)	0.004 (1)	0.0035 (9)	−0.002 (1)
C1	0.023 (1)	0.023 (1)	0.035 (2)	0.000 (1)	0.005 (1)	0.001 (1)
C2	0.029 (1)	0.026 (1)	0.035 (2)	0.007 (1)	0.008 (1)	−0.001 (1)
C3	0.023 (1)	0.036 (2)	0.027 (1)	0.003 (1)	0.004 (1)	0.003 (1)
C4	0.024 (2)	0.046 (2)	0.041 (2)	0.007 (1)	0.006 (1)	−0.001 (1)
C5	0.022 (1)	0.061 (2)	0.042 (2)	0.003 (2)	0.002 (1)	0.000 (2)
C6	0.028 (2)	0.054 (2)	0.039 (2)	−0.011 (1)	−0.001 (1)	−0.009 (2)
C7	0.034 (2)	0.039 (2)	0.035 (2)	−0.002 (1)	0.004 (1)	−0.007 (1)
C8	0.025 (1)	0.032 (1)	0.028 (1)	0.000 (1)	0.006 (1)	0.001 (1)
C9	0.025 (1)	0.029 (2)	0.036 (2)	0.004 (1)	0.006 (1)	−0.002 (1)
C10	0.029 (2)	0.026 (1)	0.035 (2)	−0.001 (1)	0.008 (1)	0.000 (1)
C11	0.047 (2)	0.073 (3)	0.047 (2)	−0.005 (2)	−0.008 (2)	0.013 (2)

Geometric parameters (Å, º)

Fe1—O1	2.050 (2)	C3—C8	1.415 (5)
Fe1—O1M	2.196 (2)	C4—C5	1.356 (5)
Fe1—N1	2.167 (2)	C4—H4	0.930
O1—C10	1.262 (4)	C5—C6	1.415 (5)
O1M—C11	1.421 (4)	C5—H5	0.930
O1M—H1M	0.966	C6—C7	1.362 (4)
O2—C10	1.239 (4)	C6—H6	0.930
N1—C1	1.372 (4)	C7—C8	1.405 (4)
N1—C9	1.315 (4)	C7—H7	0.930
C1—C2	1.366 (4)	C8—C9	1.416 (4)
C1—C10	1.519 (4)	C9—H9	0.930
C2—C3	1.414 (4)	C11—H11A	0.960
C2—H2	0.930	C11—H11B	0.960
C3—C4	1.420 (4)	C11—H11C	0.960
O1···O1^i	3.423 (4)	O2···N1^iii	3.541 (3)
O1···O1M^i	3.554 (3)	C1···C5^v	3.341 (5)
O1M···O2^i	2.617 (3)	C2···C5^v	3.478 (4)
O1M···C10^i	3.403 (4)	C2···C6^v	3.556 (5)
O1M···C5^ii	3.522 (4)	C3···C3^v	3.441 (6)
O2···C9^iii	3.280 (4)	C3···C4^v	3.566 (4)
O2···C4^iv	3.336 (4)	C4···C7^vi	3.573 (5)
O2···C11^i	3.370 (4)
O1—Fe1—O1^vii	180.0	C2—C3—C8	117.4 (3)
O1—Fe1—O1M	89.97 (9)	C4—C3—C8	119.3 (3)
O1—Fe1—O1M^vii	90.03 (9)	C3—C4—C5	119.5 (3)
O1—Fe1—N1	78.86 (9)	C3—C4—H4	120.2
O1—Fe1—N1^vii	101.14 (9)	C5—C4—H4	120.2
O1^vii—Fe1—O1M	90.03 (9)	C4—C5—C6	121.3 (3)
O1^vii—Fe1—O1M^vii	89.97 (9)	C4—C5—H5	119.3
O1^vii—Fe1—N1	101.14 (9)	C6—C5—H5	119.3
O1^vii—Fe1—N1^vii	78.86 (9)	C5—C6—C7	120.0 (3)
O1M—Fe1—O1M^vii	180.0	C5—C6—H6	120.0
O1M—Fe1—N1	92.43 (9)	C7—C6—H6	120.0
O1M—Fe1—N1^vii	87.57 (9)	C6—C7—C8	120.4 (3)
O1M^vii—Fe1—N1	87.57 (9)	C6—C7—H7	119.8
O1M^vii—Fe1—N1^vii	92.43 (9)	C8—C7—H7	119.8
N1—Fe1—N1^vii	180.0	C3—C8—C7	119.5 (3)
Fe1—O1—C10	118.1 (2)	C3—C8—C9	117.9 (3)
Fe1—O1M—C11	125.9 (2)	C7—C8—C9	122.6 (3)
Fe1—O1M—H1M	114.4	N1—C9—C8	123.6 (3)
C11—O1M—H1M	104.1	N1—C9—H9	118.2
Fe1—N1—C1	110.6 (2)	C8—C9—H9	118.2
Fe1—N1—C9	130.8 (2)	O1—C10—O2	126.4 (3)
C1—N1—C9	118.6 (2)	O1—C10—C1	116.7 (3)
N1—C1—C2	122.2 (3)	O2—C10—C1	116.9 (3)
N1—C1—C10	115.6 (2)	O1M—C11—H11A	109.5
C2—C1—C10	122.2 (3)	O1M—C11—H11B	109.5
C1—C2—C3	120.3 (3)	O1M—C11—H11C	109.5
C1—C2—H2	119.9	H11A—C11—H11B	109.5
C3—C2—H2	119.9	H11A—C11—H11C	109.5
C2—C3—C4	123.3 (3)	H11B—C11—H11C	109.5
Fe1—O1—C10—O2	178.0 (3)	N1—C1—C2—H2	178.3
Fe1—O1—C10—C1	−3.2 (4)	N1—C9—C8—C3	−1.1 (5)
Fe1—O1^vii—C10^vii—O2^vii	−178.0 (3)	N1—C9—C8—C7	177.5 (3)
Fe1—O1^vii—C10^vii—C1^vii	3.2 (4)	C1—N1—C9—C8	−0.1 (5)
Fe1—O1M—C11—H11A	−79.2	C1—N1—C9—H9	179.9
Fe1—O1M—C11—H11B	160.8	C1—C2—C3—C4	−177.7 (3)
Fe1—O1M—C11—H11C	40.8	C1—C2—C3—C8	0.4 (5)
Fe1—O1M^vii—C11^vii—H11A^vii	79.2	C2—C1—N1—C9	1.5 (5)
Fe1—O1M^vii—C11^vii—H11B^vii	−160.8	C2—C3—C4—C5	177.1 (3)
Fe1—O1M^vii—C11^vii—H11C^vii	−40.8	C2—C3—C4—H4	−2.9
Fe1—N1—C1—C2	−179.0 (2)	C2—C3—C8—C7	−177.8 (3)
Fe1—N1—C1—C10	3.3 (3)	C2—C3—C8—C9	0.9 (4)
Fe1—N1—C9—C8	−179.4 (2)	C3—C2—C1—C10	175.8 (3)
Fe1—N1—C9—H9	0.6	C3—C4—C5—C6	0.9 (5)
Fe1—N1^vii—C1^vii—C2^vii	179.0 (2)	C3—C4—C5—H5	−179.1
Fe1—N1^vii—C1^vii—C10^vii	−3.3 (3)	C3—C8—C7—C6	0.3 (5)
Fe1—N1^vii—C9^vii—C8^vii	179.4 (2)	C3—C8—C7—H7	−179.7
Fe1—N1^vii—C9^vii—H9^vii	−0.6	C3—C8—C9—H9	178.9
O1—Fe1—O1M—C11	81.5 (3)	C4—C3—C2—H2	2.4
O1—Fe1—O1M—H1M	−49.7	C4—C3—C8—C7	0.4 (5)
O1—Fe1—O1M^vii—C11^vii	98.5 (3)	C4—C3—C8—C9	179.1 (3)
O1—Fe1—O1M^vii—H1M^vii	−130.3	C4—C5—C6—C7	−0.3 (5)
O1—Fe1—N1—C1	−3.7 (2)	C4—C5—C6—H6	179.7
O1—Fe1—N1—C9	175.6 (3)	C5—C4—C3—C8	−1.0 (5)
O1—Fe1—N1^vii—C1^vii	−176.3 (2)	C5—C6—C7—C8	−0.4 (5)
O1—Fe1—N1^vii—C9^vii	4.4 (3)	C5—C6—C7—H7	179.6
O1—C10—C1—N1	−0.3 (4)	C6—C5—C4—H4	−179.1
O1—C10—C1—C2	−178.0 (3)	C6—C7—C8—C9	−178.3 (3)
O1M—Fe1—O1—C10	−88.6 (2)	C7—C6—C5—H5	179.7
O1M—Fe1—O1^vii—C10^vii	−91.4 (2)	C7—C8—C9—H9	−2.4
O1M—Fe1—N1—C1	85.8 (2)	C8—C3—C2—H2	−179.6
O1M—Fe1—N1—C9	−94.9 (3)	C8—C3—C4—H4	179.0
O1M—Fe1—N1^vii—C1^vii	94.2 (2)	C8—C7—C6—H6	179.7
O1M—Fe1—N1^vii—C9^vii	−85.1 (3)	C9—N1—C1—C10	−176.1 (3)
O2—C10—C1—N1	178.5 (3)	C9—C8—C7—H7	1.7
O2—C10—C1—C2	0.9 (5)	C10—C1—C2—H2	−4.2
N1—Fe1—O1—C10	3.9 (2)	H1M—O1M—C11—H11A	55.9
N1—Fe1—O1^vii—C10^vii	176.1 (2)	H1M—O1M—C11—H11B	−64.1
N1—Fe1—O1M—C11	2.7 (3)	H1M—O1M—C11—H11C	175.9
N1—Fe1—O1M—H1M	−128.5	H4—C4—C5—H5	0.9
N1—Fe1—O1M^vii—C11^vii	177.3 (3)	H5—C5—C6—H6	−0.3
N1—Fe1—O1M^vii—H1M^vii	−51.5	H6—C6—C7—H7	−0.3
N1—C1—C2—C3	−1.7 (5)	H6—C6—C7—H7	−0.3

Symmetry codes: (i) −x, −y−1, −z; (ii) x−1, y, z; (iii) x, y−1, z; (iv) −x+1, −y−1, −z; (v) −x+1, −y, −z; (vi) −x+1, y−1/2, −z+1/2; (vii) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1M—H1M···O2^i	0.97	1.66	2.617 (3)	170.32

Symmetry code: (i) −x, −y−1, −z.