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

Okabe, N.; Muranishi, Y.

doi:10.1107/S160053680301972X

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301972X/cv6229sup1.cif Contains datablocks General, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680301972X/cv6229Isup2.hkl Contains datablock I

CCDC reference: 225669

checkCIF report

Key indicators

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

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No errors found in this datablock

Computing details top

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) top

Crystal data top

C₂₂H₂₀FeN₂O₆	F(000) = 480.0
M_r = 464.25	D_x = 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) Å³	0.40 × 0.10 × 0.10 mm
Z = 2

Data collection top

Rigaku AFC5R diffractometer	R_int = 0.024
ω–2θ scans	θ_max = 27.5°
Absorption correction: ψ scan (North, Phillips & Mathews, 1968)	h = 0→14
T_min = 0.909, T_max = 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 top

Refinement on F²	H-atom parameters not refined
R[F² > 2σ(F²)] = 0.039	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.141	(Δ/σ)_max < 0.001
S = 0.86	Δρ_max = 0.37 e Å⁻³
2301 reflections	Δρ_min = −0.36 e Å⁻³
143 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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···O1ⁱ	3.423 (4)	O2···N1ⁱⁱⁱ	3.541 (3)
O1···O1Mⁱ	3.554 (3)	C1···C5^v	3.341 (5)
O1M···O2ⁱ	2.617 (3)	C2···C5^v	3.478 (4)
O1M···C10ⁱ	3.403 (4)	C2···C6^v	3.556 (5)
O1M···C5ⁱⁱ	3.522 (4)	C3···C3^v	3.441 (6)
O2···C9ⁱⁱⁱ	3.280 (4)	C3···C4^v	3.566 (4)
O2···C4^iv	3.336 (4)	C4···C7^vi	3.573 (5)
O2···C11ⁱ	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) top

D—H···A	D—H	H···A	D···A	D—H···A
O1M—H1M···O2ⁱ	0.97	1.66	2.617 (3)	170.32

Symmetry code: (i) −x, −y−1, −z.

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

Supporting information

Key indicators

checkCIF/PLATON results

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