4-Methyl-2,7-dioxo-3,6-dioxa-1(1,1′)-ferrocenacyclo­hepta­phane

Leng, X.; Yang, B.; Zhang, P.; Fang, X.

doi:10.1107/S1600536811019398

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m947

doi:10.1107/S1600536811019398

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4-Methyl-2,7-dioxo-3,6-dioxa-1(1,1′)-ferrocenacycloheptaphane

Xin Leng,^a Bingqin Yang,^a ^* Pengfei Zhang ^a and Xianwen Fang ^a

^aKey Laboratory of Synthetic and Natural Chemistry of the Ministry of Education, College of Chemistry and Materials Science, Northwest University of Xi'an, Taibai Bei Avenue 229, Xi'an 710069, Shaanxi, People's Republic of China
^*Correspondence e-mail: yangbq@nwu.edu.cn

(Received 15 May 2011; accepted 23 May 2011; online 18 June 2011)

In the title compound, [Fe(C₁₅H₁₄O₄)], the two cyclopentadienyl (Cp) rings are nearly parallel, making a dihedral angle of 2.6 (1)°. The distance between the centroids of the Cp rings is 3.309 (8) Å. The relative orientation of the two Cp rings is characterized by a torsion angle of −43.99 (6)° defined by the two centroids and the two substituted C atoms.

Related literature

For the definition of ferrocenophanes, see: Otón et al. (2005 ). For the properties of ferrocenophanes, see: Cayuela et al. (2004 ); Kulbaba & Manners (2001 ); Lu et al. (2006 ); Mizuta et al. (2003 ); Nguyen et al. (1999 ); Otón et al. (2006a ,b ); Suzaki et al. (2006 ). For the synthesis and related structures, see: Gao et al. (2009 ); Leng et al. (2010 ). For studies of host structures for the investigation of molecular recognition, see: Bond et al. (2009 ); Choi et al. (2006 ); Nakagaki et al. (2010 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

[Fe(C₁₅H₁₄O₄)]
M_r = 314.11
Monoclinic, C c
a = 7.1665 (14) Å
b = 20.131 (4) Å
c = 9.2464 (19) Å
β = 103.193 (2)°
V = 1298.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.17 mm⁻¹
T = 296 K
0.29 × 0.21 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.727, T_max = 0.870
3177 measured reflections
1971 independent reflections
1721 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.087
S = 0.96
1971 reflections
182 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.41 e Å⁻³
Absolute structure: Flack (1983 ), 812 Friedel pairs
Flack parameter: 0.03 (3)

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019398/hy2432sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019398/hy2432Isup2.hkl

checkCIF report

Comment top

Ferrocenophanes, in which the two cyclopentadienyl (Cp) rings are joined by an atomic or molecular bridge (Otón et al., 2005), are found to be aromatic, highly stable and generally non-toxic, and have rversible redox characteristics (Mizuta et al., 2003). In particular, ferrocenophanes are useful precursors to poly-ferrocenyl materials (Kulbaba & Manners, 2001; Nguyen et al., 1999) and act as potentical receptor towards cation or anion recognition (Cayuela et al., 2004; Lu et al., 2006; Otón et al., 2006a,b; Suzaki et al., 2006). As a part of our ongoing investigation of ferrocenphanes, the title compound has been prepared and we report its crystal structure. Despite of the fact that structurally characterized ferrocenophanes are well presented in the Cambridge Structural Database (Allen, 2002; Version 5.27, release February 2009), there are only a few of structurally characterized compounds (Gao et al., 2009; Leng et al., 2010). Meanwhile, the study of the host structures is very helpful for the investigation of molecular recognition (Bond et al., 2009; Choi et al., 2006; Nakagaki et al., 2010). From this viewpoint, X-ray single-crystal study of the title compound presents a certain descriptive interest.

The structure of the title compound is shown in Fig. 1. The two cyclopentadienyl (Cp) rings are nearly parallel, making a dihedral angle of 2.6 (1)°. The distance between the centroids of the Cp rings is 3.309 (8) Å. The angle formed between the two centroids and Fe1 is 179.4 (6)°. The relative orientation of the two Cp rings is characterized by the C6—Cg1—Cg2—C9 torsion angle of -43.99 (6)° (Cg1 and Cg2 are the centroids of C1–C5 ring and C10–C14 ring, respectively). The Fe—C distances range from 2.027 (5) to 2.073 (5) Å. The exocyclic C5—C6 and C9—C10 bond lengths are 1.456 (7) and 1.461 (9) Å.

Related literature top

For the definition of ferrocenophanes, see: Otón et al. (2005). For the properties of ferrocenophanes, see: Cayuela et al. (2004); Kulbaba & Manners (2001); Lu et al. (2006); Mizuta et al. (2003); Nguyen et al. (1999); Otón et al. (2006a,b); Suzaki et al. (2006). For the synthesis and related structures, see: Gao et al. (2009); Leng et al. (2010). For the investigation of host structures for the investigation of molecular recognition, see: Bond et al. (2009); Choi et al. (2006); Nakagaki et al. (2010). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

The title compound was synthesized according to the published procedure (Gao et al., 2009). Melting point, IR and NMR spectra confirmed identity and purity of the prepared compound.

Yellow crystals of the title compoud suitable for X-ray diffraction analysis were obtained by slow concentration of a dichloromethane solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

propane-1,2-diyl ferrocene-1,1'-dicarboxylate top

Crystal data top

[Fe(C₁₅H₁₄O₄)]	Z = 4
M_r = 314.11	F(000) = 648
Monoclinic, Cc	D_x = 1.606 Mg m⁻³
Hall symbol: C -2yc	Melting point: 405(6) K
a = 7.1665 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 20.131 (4) Å	µ = 1.17 mm⁻¹
c = 9.2464 (19) Å	T = 296 K
β = 103.193 (2)°	Block, yellow
V = 1298.7 (4) Å³	0.29 × 0.21 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	1971 independent reflections
Radiation source: fine-focus sealed tube	1721 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.727, T_max = 0.870	k = −24→21
3177 measured reflections	l = −8→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0495P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max < 0.001
1971 reflections	Δρ_max = 0.30 e Å⁻³
182 parameters	Δρ_min = −0.41 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 812 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (3)

Crystal data top

[Fe(C₁₅H₁₄O₄)]	V = 1298.7 (4) Å³
M_r = 314.11	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 7.1665 (14) Å	µ = 1.17 mm⁻¹
b = 20.131 (4) Å	T = 296 K
c = 9.2464 (19) Å	0.29 × 0.21 × 0.12 mm
β = 103.193 (2)°

Data collection top

Bruker APEXII CCD diffractometer	1971 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1721 reflections with I > 2σ(I)
T_min = 0.727, T_max = 0.870	R_int = 0.024
3177 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.087	Δρ_max = 0.30 e Å⁻³
S = 0.96	Δρ_min = −0.41 e Å⁻³
1971 reflections	Absolute structure: Flack (1983), 812 Friedel pairs
182 parameters	Absolute structure parameter: 0.03 (3)
2 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Fe1	0.13087 (9)	0.36266 (2)	0.68667 (8)	0.04130 (18)
O1	0.5456 (6)	0.47208 (16)	0.8549 (4)	0.0654 (10)
O2	0.5650 (4)	0.37627 (13)	0.9814 (3)	0.0426 (7)
O3	0.2545 (5)	0.40433 (17)	1.0838 (4)	0.0562 (8)
O4	0.1738 (6)	0.2959 (2)	1.0643 (5)	0.0820 (12)
C1	0.3338 (7)	0.3998 (3)	0.5860 (6)	0.0522 (13)
H1	0.3431	0.4459	0.5541	0.063*
C2	0.2339 (10)	0.3478 (4)	0.4983 (7)	0.0609 (17)
H2	0.1593	0.3520	0.3957	0.073*
C3	0.2568 (7)	0.2893 (3)	0.5836 (6)	0.0523 (12)
H3	0.2011	0.2458	0.5510	0.063*
C4	0.3700 (7)	0.3047 (2)	0.7267 (5)	0.0480 (11)
H4	0.4074	0.2732	0.8091	0.058*
C5	0.4210 (9)	0.3728 (3)	0.7309 (7)	0.0404 (13)
C6	0.5160 (6)	0.4129 (2)	0.8576 (5)	0.0408 (10)
C7	0.5946 (7)	0.4116 (2)	1.1239 (5)	0.0465 (11)
H7	0.5878	0.4596	1.1062	0.056*
C8	0.4317 (8)	0.3902 (3)	1.1916 (7)	0.0585 (15)
H8A	0.4410	0.3431	1.2142	0.070*
H8B	0.4356	0.4144	1.2829	0.070*
C9	0.1550 (7)	0.3512 (3)	1.0141 (6)	0.0547 (13)
C10	0.0267 (9)	0.3693 (3)	0.8729 (7)	0.0475 (15)
C11	−0.0857 (7)	0.3239 (3)	0.7722 (6)	0.0592 (14)
H11	−0.1055	0.2768	0.7911	0.071*
C12	−0.1631 (11)	0.3581 (4)	0.6428 (9)	0.069 (2)
H12	−0.2445	0.3383	0.5536	0.083*
C13	−0.1028 (7)	0.4244 (3)	0.6556 (7)	0.0655 (15)
H13	−0.1372	0.4589	0.5793	0.079*
C14	0.0168 (8)	0.4324 (3)	0.7992 (6)	0.0582 (13)
H14	0.0788	0.4737	0.8414	0.070*
C15	0.7879 (9)	0.3938 (3)	1.2184 (7)	0.0636 (16)
H15A	0.7961	0.3465	1.2321	0.095*
H15B	0.8050	0.4152	1.3133	0.095*
H15C	0.8861	0.4083	1.1703	0.095*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0369 (3)	0.0492 (3)	0.0394 (3)	0.0023 (3)	0.0120 (2)	0.0010 (4)
O1	0.093 (3)	0.053 (2)	0.048 (2)	−0.0180 (17)	0.012 (2)	0.0077 (16)
O2	0.0533 (18)	0.0433 (16)	0.0294 (16)	0.0043 (13)	0.0056 (14)	−0.0023 (13)
O3	0.0564 (19)	0.066 (2)	0.049 (2)	−0.0042 (16)	0.0175 (17)	−0.0113 (16)
O4	0.095 (3)	0.086 (3)	0.059 (3)	−0.036 (2)	0.004 (2)	0.014 (2)
C1	0.046 (3)	0.071 (4)	0.043 (3)	−0.004 (3)	0.016 (2)	0.012 (3)
C2	0.058 (4)	0.090 (4)	0.038 (4)	−0.010 (3)	0.016 (3)	−0.011 (3)
C3	0.050 (3)	0.060 (3)	0.046 (3)	0.008 (2)	0.010 (2)	−0.008 (2)
C4	0.052 (3)	0.051 (3)	0.042 (3)	0.005 (2)	0.012 (2)	−0.006 (2)
C5	0.037 (3)	0.052 (3)	0.034 (3)	−0.002 (2)	0.011 (3)	−0.002 (2)
C6	0.039 (2)	0.049 (3)	0.036 (3)	0.0002 (19)	0.012 (2)	0.004 (2)
C7	0.062 (3)	0.044 (2)	0.032 (2)	−0.001 (2)	0.008 (2)	−0.0051 (18)
C8	0.067 (4)	0.072 (3)	0.036 (3)	−0.016 (3)	0.013 (3)	−0.007 (2)
C9	0.052 (3)	0.071 (4)	0.050 (3)	−0.015 (2)	0.028 (2)	−0.002 (2)
C10	0.031 (3)	0.074 (4)	0.041 (4)	0.000 (2)	0.014 (3)	−0.004 (2)
C11	0.045 (3)	0.079 (4)	0.057 (4)	−0.014 (3)	0.019 (3)	−0.016 (3)
C12	0.031 (3)	0.121 (7)	0.055 (5)	0.003 (3)	0.010 (3)	−0.015 (4)
C13	0.051 (3)	0.084 (4)	0.062 (4)	0.019 (3)	0.013 (3)	−0.002 (3)
C14	0.050 (3)	0.068 (3)	0.060 (4)	0.014 (2)	0.018 (3)	−0.009 (3)
C15	0.065 (3)	0.071 (4)	0.046 (3)	0.004 (3)	−0.005 (3)	−0.013 (3)

Geometric parameters (Å, º) top

Fe1—C14	2.027 (5)	C3—H3	0.9800
Fe1—C5	2.036 (6)	C4—C5	1.418 (7)
Fe1—C4	2.037 (5)	C4—H4	0.9800
Fe1—C10	2.032 (6)	C5—C6	1.456 (7)
Fe1—C1	2.040 (5)	C7—C15	1.503 (7)
Fe1—C12	2.054 (8)	C7—C8	1.508 (7)
Fe1—C13	2.053 (5)	C7—H7	0.9800
Fe1—C11	2.051 (5)	C8—H8A	0.9700
Fe1—C2	2.063 (6)	C8—H8B	0.9700
Fe1—C3	2.073 (5)	C9—C10	1.461 (9)
O1—C6	1.212 (5)	C10—C11	1.418 (7)
O2—C6	1.339 (5)	C10—C14	1.437 (7)
O2—C7	1.469 (5)	C11—C12	1.382 (10)
O3—C9	1.362 (6)	C11—H11	0.9800
O3—C8	1.452 (7)	C12—C13	1.401 (8)
O4—C9	1.202 (6)	C12—H12	0.9800
C1—C2	1.415 (9)	C13—C14	1.416 (8)
C1—C5	1.449 (8)	C13—H13	0.9800
C1—H1	0.9800	C14—H14	0.9800
C2—C3	1.406 (9)	C15—H15A	0.9600
C2—H2	0.9800	C15—H15B	0.9600
C3—C4	1.419 (6)	C15—H15C	0.9600

C14—Fe1—C5	109.9 (2)	C3—C4—Fe1	71.2 (3)
C14—Fe1—C4	136.5 (2)	C5—C4—Fe1	69.6 (3)
C5—Fe1—C4	40.76 (18)	C3—C4—H4	125.5
C14—Fe1—C10	41.5 (2)	C5—C4—H4	125.5
C5—Fe1—C10	112.3 (2)	Fe1—C4—H4	125.5
C4—Fe1—C10	109.9 (2)	C4—C5—C6	128.9 (5)
C14—Fe1—C1	113.2 (3)	C4—C5—C1	106.4 (5)
C5—Fe1—C1	41.7 (2)	C6—C5—C1	124.1 (4)
C4—Fe1—C1	68.6 (2)	C4—C5—Fe1	69.7 (3)
C10—Fe1—C1	143.3 (2)	C6—C5—Fe1	119.1 (4)
C14—Fe1—C12	67.5 (3)	C1—C5—Fe1	69.3 (3)
C5—Fe1—C12	176.8 (2)	O1—C6—O2	123.1 (4)
C4—Fe1—C12	142.4 (3)	O1—C6—C5	125.4 (4)
C10—Fe1—C12	67.1 (3)	O2—C6—C5	111.5 (4)
C1—Fe1—C12	137.1 (3)	O2—C7—C15	109.4 (4)
C14—Fe1—C13	40.6 (2)	O2—C7—C8	105.5 (4)
C5—Fe1—C13	136.9 (2)	C15—C7—C8	112.9 (5)
C4—Fe1—C13	176.9 (2)	O2—C7—H7	109.7
C10—Fe1—C13	68.5 (2)	C15—C7—H7	109.7
C1—Fe1—C13	111.0 (2)	C8—C7—H7	109.7
C12—Fe1—C13	39.9 (2)	O3—C8—C7	107.3 (5)
C14—Fe1—C11	68.7 (2)	O3—C8—H8A	110.2
C5—Fe1—C11	142.1 (2)	C7—C8—H8A	110.2
C4—Fe1—C11	113.0 (2)	O3—C8—H8B	110.2
C10—Fe1—C11	40.6 (2)	C7—C8—H8B	110.2
C1—Fe1—C11	175.7 (2)	H8A—C8—H8B	108.5
C12—Fe1—C11	39.3 (3)	O4—C9—O3	122.9 (5)
C13—Fe1—C11	67.6 (3)	O4—C9—C10	124.6 (5)
C14—Fe1—C2	142.9 (3)	O3—C9—C10	112.5 (5)
C5—Fe1—C2	68.8 (3)	C11—C10—C14	107.4 (5)
C4—Fe1—C2	67.8 (3)	C11—C10—C9	125.1 (5)
C10—Fe1—C2	175.4 (3)	C14—C10—C9	126.6 (5)
C1—Fe1—C2	40.3 (2)	C11—C10—Fe1	70.4 (3)
C12—Fe1—C2	112.0 (3)	C14—C10—Fe1	69.1 (3)
C13—Fe1—C2	114.0 (3)	C9—C10—Fe1	117.6 (4)
C11—Fe1—C2	135.9 (3)	C12—C11—C10	107.6 (6)
C14—Fe1—C3	176.6 (2)	C12—C11—Fe1	70.5 (4)
C5—Fe1—C3	68.4 (2)	C10—C11—Fe1	69.0 (3)
C4—Fe1—C3	40.38 (18)	C12—C11—H11	126.2
C10—Fe1—C3	136.0 (2)	C10—C11—H11	126.2
C1—Fe1—C3	67.7 (2)	Fe1—C11—H11	126.2
C12—Fe1—C3	114.3 (2)	C11—C12—C13	110.3 (7)
C13—Fe1—C3	142.6 (2)	C11—C12—Fe1	70.2 (4)
C11—Fe1—C3	110.7 (2)	C13—C12—Fe1	70.0 (4)
C2—Fe1—C3	39.7 (2)	C11—C12—H12	124.8
C6—O2—C7	117.2 (3)	C13—C12—H12	124.8
C9—O3—C8	116.9 (4)	Fe1—C12—H12	124.8
C2—C1—C5	107.9 (5)	C12—C13—C14	107.2 (6)
C2—C1—Fe1	70.7 (3)	C12—C13—Fe1	70.1 (4)
C5—C1—Fe1	69.0 (3)	C14—C13—Fe1	68.7 (3)
C2—C1—H1	126.0	C12—C13—H13	126.4
C5—C1—H1	126.0	C14—C13—H13	126.4
Fe1—C1—H1	126.0	Fe1—C13—H13	126.4
C3—C2—C1	108.6 (6)	C13—C14—C10	107.4 (5)
C3—C2—Fe1	70.5 (3)	C13—C14—Fe1	70.7 (3)
C1—C2—Fe1	68.9 (3)	C10—C14—Fe1	69.4 (3)
C3—C2—H2	125.7	C13—C14—H14	126.3
C1—C2—H2	125.7	C10—C14—H14	126.3
Fe1—C2—H2	125.7	Fe1—C14—H14	126.3
C2—C3—C4	108.0 (5)	C7—C15—H15A	109.5
C2—C3—Fe1	69.8 (3)	C7—C15—H15B	109.5
C4—C3—Fe1	68.4 (3)	H15A—C15—H15B	109.5
C2—C3—H3	126.0	C7—C15—H15C	109.5
C4—C3—H3	126.0	H15A—C15—H15C	109.5
Fe1—C3—H3	126.0	H15B—C15—H15C	109.5
C3—C4—C5	109.0 (5)

C14—Fe1—C1—C2	−146.8 (4)	O2—C7—C8—O3	−55.2 (5)
C5—Fe1—C1—C2	118.9 (5)	C15—C7—C8—O3	−174.6 (4)
C4—Fe1—C1—C2	80.4 (4)	C8—O3—C9—O4	21.6 (7)
C10—Fe1—C1—C2	175.4 (5)	C8—O3—C9—C10	−157.7 (5)
C12—Fe1—C1—C2	−65.5 (6)	O4—C9—C10—C11	−3.3 (9)
C13—Fe1—C1—C2	−102.9 (4)	O3—C9—C10—C11	176.0 (5)
C3—Fe1—C1—C2	36.8 (4)	O4—C9—C10—C14	−171.4 (6)
C14—Fe1—C1—C5	94.3 (3)	O3—C9—C10—C14	7.9 (8)
C4—Fe1—C1—C5	−38.5 (3)	O4—C9—C10—Fe1	−87.9 (6)
C10—Fe1—C1—C5	56.4 (5)	O3—C9—C10—Fe1	91.5 (5)
C12—Fe1—C1—C5	175.6 (4)	C14—Fe1—C10—C11	118.4 (5)
C13—Fe1—C1—C5	138.2 (3)	C5—Fe1—C10—C11	−146.3 (3)
C2—Fe1—C1—C5	−118.9 (5)	C4—Fe1—C10—C11	−102.5 (3)
C3—Fe1—C1—C5	−82.1 (3)	C1—Fe1—C10—C11	176.9 (4)
C5—C1—C2—C3	−0.3 (7)	C12—Fe1—C10—C11	37.1 (4)
Fe1—C1—C2—C3	−59.5 (4)	C13—Fe1—C10—C11	80.3 (4)
C5—C1—C2—Fe1	59.2 (4)	C3—Fe1—C10—C11	−64.8 (5)
C14—Fe1—C2—C3	176.6 (4)	C5—Fe1—C10—C14	95.2 (4)
C5—Fe1—C2—C3	81.3 (4)	C4—Fe1—C10—C14	139.0 (3)
C4—Fe1—C2—C3	37.3 (3)	C1—Fe1—C10—C14	58.5 (5)
C1—Fe1—C2—C3	119.9 (5)	C12—Fe1—C10—C14	−81.4 (4)
C12—Fe1—C2—C3	−102.0 (4)	C13—Fe1—C10—C14	−38.1 (3)
C13—Fe1—C2—C3	−145.5 (3)	C11—Fe1—C10—C14	−118.4 (5)
C11—Fe1—C2—C3	−63.4 (5)	C3—Fe1—C10—C14	176.7 (3)
C14—Fe1—C2—C1	56.7 (6)	C14—Fe1—C10—C9	−121.4 (6)
C5—Fe1—C2—C1	−38.6 (3)	C5—Fe1—C10—C9	−26.2 (5)
C4—Fe1—C2—C1	−82.6 (4)	C4—Fe1—C10—C9	17.6 (4)
C12—Fe1—C2—C1	138.1 (4)	C1—Fe1—C10—C9	−62.9 (5)
C13—Fe1—C2—C1	94.6 (4)	C12—Fe1—C10—C9	157.2 (5)
C11—Fe1—C2—C1	176.7 (4)	C13—Fe1—C10—C9	−159.6 (5)
C3—Fe1—C2—C1	−119.9 (5)	C11—Fe1—C10—C9	120.1 (5)
C1—C2—C3—C4	0.7 (7)	C3—Fe1—C10—C9	55.3 (5)
Fe1—C2—C3—C4	−57.9 (4)	C14—C10—C11—C12	−0.7 (6)
C1—C2—C3—Fe1	58.6 (4)	C9—C10—C11—C12	−170.7 (6)
C5—Fe1—C3—C2	−82.4 (4)	Fe1—C10—C11—C12	−60.1 (4)
C4—Fe1—C3—C2	−120.0 (5)	C14—C10—C11—Fe1	59.4 (4)
C10—Fe1—C3—C2	177.4 (5)	C9—C10—C11—Fe1	−110.5 (6)
C1—Fe1—C3—C2	−37.3 (4)	C14—Fe1—C11—C12	80.1 (4)
C12—Fe1—C3—C2	95.8 (4)	C5—Fe1—C11—C12	175.4 (4)
C13—Fe1—C3—C2	58.5 (6)	C4—Fe1—C11—C12	−147.1 (4)
C11—Fe1—C3—C2	138.3 (4)	C10—Fe1—C11—C12	118.7 (5)
C5—Fe1—C3—C4	37.6 (3)	C13—Fe1—C11—C12	36.2 (4)
C10—Fe1—C3—C4	−62.6 (4)	C2—Fe1—C11—C12	−65.8 (6)
C1—Fe1—C3—C4	82.7 (3)	C3—Fe1—C11—C12	−103.5 (4)
C12—Fe1—C3—C4	−144.2 (4)	C14—Fe1—C11—C10	−38.7 (3)
C13—Fe1—C3—C4	178.5 (4)	C5—Fe1—C11—C10	56.7 (5)
C11—Fe1—C3—C4	−101.6 (3)	C4—Fe1—C11—C10	94.2 (3)
C2—Fe1—C3—C4	120.0 (5)	C12—Fe1—C11—C10	−118.7 (5)
C2—C3—C4—C5	−0.8 (6)	C13—Fe1—C11—C10	−82.5 (4)
Fe1—C3—C4—C5	−59.5 (4)	C2—Fe1—C11—C10	175.4 (5)
C2—C3—C4—Fe1	58.7 (4)	C3—Fe1—C11—C10	137.8 (3)
C14—Fe1—C4—C3	178.1 (4)	C10—C11—C12—C13	0.6 (7)
C5—Fe1—C4—C3	−119.6 (5)	Fe1—C11—C12—C13	−58.6 (5)
C10—Fe1—C4—C3	139.0 (3)	C10—C11—C12—Fe1	59.2 (4)
C1—Fe1—C4—C3	−80.3 (3)	C14—Fe1—C12—C11	−83.4 (4)
C12—Fe1—C4—C3	60.9 (5)	C4—Fe1—C12—C11	55.0 (6)
C11—Fe1—C4—C3	95.3 (3)	C10—Fe1—C12—C11	−38.3 (4)
C2—Fe1—C4—C3	−36.7 (3)	C1—Fe1—C12—C11	176.2 (4)
C14—Fe1—C4—C5	−62.3 (4)	C13—Fe1—C12—C11	−121.6 (6)
C10—Fe1—C4—C5	−101.4 (3)	C2—Fe1—C12—C11	136.8 (4)
C1—Fe1—C4—C5	39.3 (3)	C3—Fe1—C12—C11	93.5 (4)
C12—Fe1—C4—C5	−179.4 (6)	C14—Fe1—C12—C13	38.2 (4)
C11—Fe1—C4—C5	−145.1 (3)	C4—Fe1—C12—C13	176.7 (4)
C2—Fe1—C4—C5	82.9 (4)	C10—Fe1—C12—C13	83.3 (4)
C3—Fe1—C4—C5	119.6 (5)	C1—Fe1—C12—C13	−62.2 (6)
C3—C4—C5—C6	172.0 (5)	C11—Fe1—C12—C13	121.6 (6)
Fe1—C4—C5—C6	111.5 (6)	C2—Fe1—C12—C13	−101.6 (5)
C3—C4—C5—C1	0.6 (6)	C3—Fe1—C12—C13	−144.9 (4)
Fe1—C4—C5—C1	−59.9 (4)	C11—C12—C13—C14	−0.2 (8)
C3—C4—C5—Fe1	60.5 (3)	Fe1—C12—C13—C14	−58.9 (4)
C2—C1—C5—C4	−0.2 (6)	C11—C12—C13—Fe1	58.7 (5)
Fe1—C1—C5—C4	60.1 (4)	C14—Fe1—C13—C12	−118.6 (6)
C2—C1—C5—C6	−172.1 (6)	C5—Fe1—C13—C12	−179.7 (6)
Fe1—C1—C5—C6	−111.8 (6)	C10—Fe1—C13—C12	−79.7 (5)
C2—C1—C5—Fe1	−60.3 (4)	C1—Fe1—C13—C12	139.9 (4)
C14—Fe1—C5—C4	139.6 (3)	C11—Fe1—C13—C12	−35.7 (4)
C10—Fe1—C5—C4	95.1 (3)	C2—Fe1—C13—C12	96.1 (5)
C1—Fe1—C5—C4	−117.5 (5)	C3—Fe1—C13—C12	59.5 (6)
C13—Fe1—C5—C4	176.9 (4)	C5—Fe1—C13—C14	−61.1 (5)
C11—Fe1—C5—C4	59.0 (5)	C10—Fe1—C13—C14	38.9 (4)
C2—Fe1—C5—C4	−80.1 (4)	C1—Fe1—C13—C14	−101.5 (4)
C3—Fe1—C5—C4	−37.3 (3)	C12—Fe1—C13—C14	118.6 (6)
C14—Fe1—C5—C6	15.5 (5)	C11—Fe1—C13—C14	82.9 (4)
C4—Fe1—C5—C6	−124.1 (6)	C2—Fe1—C13—C14	−145.3 (4)
C10—Fe1—C5—C6	−29.0 (5)	C3—Fe1—C13—C14	178.1 (4)
C1—Fe1—C5—C6	118.4 (5)	C12—C13—C14—C10	−0.2 (7)
C13—Fe1—C5—C6	52.8 (6)	Fe1—C13—C14—C10	−60.0 (4)
C11—Fe1—C5—C6	−65.0 (5)	C12—C13—C14—Fe1	59.8 (4)
C2—Fe1—C5—C6	155.8 (5)	C11—C10—C14—C13	0.6 (6)
C3—Fe1—C5—C6	−161.4 (5)	C9—C10—C14—C13	170.3 (5)
C14—Fe1—C5—C1	−102.9 (4)	Fe1—C10—C14—C13	60.8 (4)
C4—Fe1—C5—C1	117.5 (5)	C11—C10—C14—Fe1	−60.2 (4)
C10—Fe1—C5—C1	−147.4 (3)	C9—C10—C14—Fe1	109.5 (6)
C13—Fe1—C5—C1	−65.6 (4)	C5—Fe1—C14—C13	140.5 (4)
C11—Fe1—C5—C1	176.6 (4)	C4—Fe1—C14—C13	178.4 (4)
C2—Fe1—C5—C1	37.4 (4)	C10—Fe1—C14—C13	−118.0 (5)
C3—Fe1—C5—C1	80.2 (3)	C1—Fe1—C14—C13	95.7 (4)
C7—O2—C6—O1	20.9 (6)	C12—Fe1—C14—C13	−37.6 (4)
C7—O2—C6—C5	−157.9 (4)	C11—Fe1—C14—C13	−80.1 (4)
C4—C5—C6—O1	−175.5 (5)	C2—Fe1—C14—C13	59.6 (6)
C1—C5—C6—O1	−5.5 (9)	C5—Fe1—C14—C10	−101.5 (4)
Fe1—C5—C6—O1	−89.0 (6)	C4—Fe1—C14—C10	−63.6 (5)
C4—C5—C6—O2	3.2 (8)	C1—Fe1—C14—C10	−146.3 (3)
C1—C5—C6—O2	173.3 (5)	C12—Fe1—C14—C10	80.4 (4)
Fe1—C5—C6—O2	89.7 (4)	C13—Fe1—C14—C10	118.0 (5)
C6—O2—C7—C15	−126.9 (5)	C11—Fe1—C14—C10	37.9 (3)
C6—O2—C7—C8	111.4 (5)	C2—Fe1—C14—C10	177.6 (5)
C9—O3—C8—C7	108.1 (5)

Experimental details

Crystal data
Chemical formula	[Fe(C₁₅H₁₄O₄)]
M_r	314.11
Crystal system, space group	Monoclinic, Cc
Temperature (K)	296
a, b, c (Å)	7.1665 (14), 20.131 (4), 9.2464 (19)
β (°)	103.193 (2)
V (Å³)	1298.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.17
Crystal size (mm)	0.29 × 0.21 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.727, 0.870
No. of measured, independent and observed [I > 2σ(I)] reflections	3177, 1971, 1721
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.087, 0.96
No. of reflections	1971
No. of parameters	182
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.41
Absolute structure	Flack (1983), 812 Friedel pairs
Absolute structure parameter	0.03 (3)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999).

Acknowledgements

Financial support from the National Natural Science Foundation of China (grant No. 20972125) is gratefully acknowledged.

References

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