2-Chloro-1-ferrocenyl­ethanone

McAdam, C.J.; Simpson, J.

doi:10.1107/S241431461502177X

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 1| January 2016| x152177

https://doi.org/10.1107/S241431461502177X

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2-Chloro-1-ferrocenylethanone

C. John McAdam ^a and Jim Simpson ^a ^*

^aDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
^*Correspondence e-mail: jsimpson@alkali.otago.ac.nz

Edited by M. Weil, Vienna University of Technology, Austria (Received 3 November 2015; accepted 16 November 2015; online 1 January 2016)

The title molecule, [Fe(C₅H₅)(C₇H₆C_lO)], comprises a ferrocene unit with a 2-chloroethanone substituent on one of the cyclopentadienyl (Cp) rings. The two Cp rings are almost coplanar with an angle of 1.28 (1)° between them. In the crystal, C—H⋯Cl and C—H⋯O hydrogen bonds together with an edge-to-face C—H⋯π contact involving the unsubstituted Cp ring stack molecules along the c-axis direction.

Keywords: crystal structure; 2-chloro-1-ferrocenylethanone; hydrogen bonding; C—H⋯π contact.

CCDC reference: 1440894

Structure description

The title compound is an important synthon for the preparation of acylferrocenyl derivatives (Liu et al., 2010 ; Bendrath et al., 2011 ; Zheng et al., (2012 ). The substituted Cp ring caries a 2-chloroethanone substituent, Fig. 1, and the Cp rings are slightly staggered with a mean C⋯Cg1⋯Cg2⋯C angle of 6.87 (19)° [Cg1 and Cg2 are the centroids of the C3–C7 and C8–C12 Cp rings, respectively]. The Cp rings are almost coplanar with an angle of 1.28 (1) ° between them, while the dihedral angle between the planar 2-chloroethanone unit (r.m.s. deviation = 0.016 Å) and the Cp ring to which it is bound is 6.07 (8)°. Bond distances and angles for the molecule are close to those found in the structure of a co-crystal of the title compound with acetylferrocene (Erben et al., 2011 ).

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

In the crystal structure, the carbonyl oxygen atom, O1, acts as a bifurcated acceptor while C9 is a bifurcated donor, with C1—H1⋯O1, C9—H9.·O1 and C9—H9⋯Cl1 hydrogen bonds, Table 1, forming rows of molecules along the bc diagonal. An additional C11—H11⋯Cl1 hydrogen bond together with an edge-to-face C1–H1A⋯π contact involving the unsubstituted Cp ring complete the contributions to the crystal packing, stacking molecules along the c-axis direction, Fig. 2.

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8–C12 Cp ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cl1ⁱ	0.95	2.88	3.4196 (19)	117
C1—H1B⋯O1ⁱⁱ	0.99	2.30	3.256 (2)	163
C9—H9⋯Cl1ⁱⁱ	0.95	2.95	3.841 (2)	157
C9—H9⋯O1ⁱⁱ	0.95	2.56	3.262 (2)	131
C1—H1A⋯Cg2ⁱⁱⁱ	0.99	2.69	3.4383 (18)	132
Symmetry codes: (i) x-1, y, z-1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (iii) x+1, y, z.

Figure 2
Crystal packing of the title compound viewed along the c-axis direction. A representative C—H⋯π contact is shown as a green dashed line. Other hydrogen bonds are drawn as blue dashed lines.

Synthesis and crystallization

The title compound was synthesised by a literature method (Fang et al., 2003 ). Crystals for the X-ray study were grown from a CH₂Cl₂ solution layered with hexane.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. checkCIF implemented in PLATON (Spek, 2009 ) signals the possibility of additional symmetry in the structure. However, the ellipsoids across the possible mirror plane are evenly sized and there is no long–short pattern of bond lengths to suggest missing symmetry. Furthermore, one ring is noticeably twisted with respect to the other, destroying mirror symmetry for the FeCp₂ units (ignoring substituents). Attempts at refinement in space group P2₁/m were singularly unsuccessful. The structure was refined as an inversion twin with a 0.691 (12):0.309 (12) domain ratio.

Table 2
Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₇H₆ClO)]
M_r	262.51
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	92
a, b, c (Å)	7.4235 (4), 9.6339 (4), 7.5209 (3)
β (°)	99.728 (2)
V (Å³)	530.14 (4)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.64
Crystal size (mm)	0.32 × 0.29 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2011 )
T_min, T_max	0.778, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9868, 3658, 3612
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.773

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.053, 1.06
No. of reflections	3658
No. of parameters	137
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.01, −0.43
Absolute structure	Refined as an inversion twin
Absolute structure parameter	0.309 (12)
Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2011), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), TITAN2000 (Hunter & Simpson, 1999 ), Mercury (Macrae et al., 2008 ), enCIFer (Allen et al., 2004 ), PLATON (Spek, 2009), publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1440894

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S241431461502177X/wm4003sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461502177X/wm4003Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: APEX2 and SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b), enCIFer (Allen et al., 2004), PLATON (Spek, 2009), publCIF (Westrip, 2010).

2-Chloro-1-ferrocenylethanone top

Crystal data top

[Fe(C₅H₅)(C₇H₆ClO)]	F(000) = 268
M_r = 262.51	D_x = 1.644 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.4235 (4) Å	Cell parameters from 8073 reflections
b = 9.6339 (4) Å	θ = 2.8–33.3°
c = 7.5209 (3) Å	µ = 1.64 mm⁻¹
β = 99.728 (2)°	T = 92 K
V = 530.14 (4) Å³	Block, orange
Z = 2	0.32 × 0.29 × 0.11 mm

Data collection top

Bruker APEXII CCD area detector diffractometer	3612 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.019
ω scans	θ_max = 33.3°, θ_min = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −11→7
T_min = 0.778, T_max = 1.000	k = −14→14
9868 measured reflections	l = −11→11
3658 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.021	w = 1/[σ²(F_o²) + (0.0301P)² + 0.0787P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.053	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 1.01 e Å⁻³
3658 reflections	Δρ_min = −0.43 e Å⁻³
137 parameters	Absolute structure: Refined as an inversion twin
1 restraint	Absolute structure parameter: 0.309 (12)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
Cl1	0.77444 (7)	0.45989 (5)	0.70617 (6)	0.02778 (11)
C1	0.6570 (2)	0.41602 (18)	0.4880 (2)	0.0159 (3)
H1A	0.7421	0.3671	0.4211	0.019*
H1B	0.5559	0.3516	0.4999	0.019*
C2	0.5800 (2)	0.54234 (17)	0.3809 (2)	0.0134 (3)
O1	0.60745 (19)	0.66056 (14)	0.4372 (2)	0.0205 (3)
C3	0.4737 (2)	0.51284 (16)	0.2015 (2)	0.0119 (3)
C4	0.4327 (2)	0.37918 (18)	0.1191 (2)	0.0142 (3)
H4	0.4760	0.2920	0.1676	0.017*
C5	0.3146 (3)	0.4020 (2)	−0.0494 (3)	0.0167 (3)
H5	0.2670	0.3323	−0.1338	0.020*
C6	0.2806 (3)	0.5478 (2)	−0.0689 (3)	0.0161 (3)
H6	0.2057	0.5913	−0.1681	0.019*
C7	0.3778 (2)	0.61677 (18)	0.0852 (2)	0.0140 (3)
H7	0.3790	0.7139	0.1072	0.017*
Fe1	0.20089 (3)	0.47611 (2)	0.16401 (2)	0.01033 (6)
C8	0.1248 (2)	0.4631 (3)	0.4129 (2)	0.0198 (3)
H8	0.2041	0.4677	0.5260	0.024*
C9	0.0737 (3)	0.3400 (2)	0.3121 (3)	0.0180 (3)
H9	0.1123	0.2483	0.3461	0.022*
C10	−0.0457 (3)	0.3791 (2)	0.1508 (3)	0.0162 (3)
H10	−0.1001	0.3177	0.0582	0.019*
C11	−0.0692 (3)	0.5260 (2)	0.1523 (2)	0.0154 (3)
H11	−0.1421	0.5795	0.0612	0.018*
C12	0.0364 (3)	0.5785 (2)	0.3151 (3)	0.0196 (4)
H12	0.0460	0.6729	0.3517	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0403 (3)	0.0232 (2)	0.01616 (16)	−0.0061 (2)	−0.00591 (16)	0.00289 (16)
C1	0.0159 (8)	0.0150 (7)	0.0158 (7)	−0.0018 (6)	0.0000 (6)	−0.0003 (6)
C2	0.0079 (7)	0.0149 (7)	0.0176 (7)	−0.0005 (5)	0.0026 (5)	−0.0010 (5)
O1	0.0180 (6)	0.0147 (6)	0.0266 (6)	0.0006 (5)	−0.0027 (5)	−0.0044 (5)
C3	0.0095 (7)	0.0117 (6)	0.0146 (6)	−0.0003 (5)	0.0026 (5)	−0.0005 (5)
C4	0.0133 (7)	0.0135 (7)	0.0161 (7)	0.0021 (6)	0.0036 (6)	−0.0021 (6)
C5	0.0193 (9)	0.0171 (8)	0.0146 (8)	0.0004 (6)	0.0054 (6)	−0.0033 (6)
C6	0.0179 (9)	0.0178 (8)	0.0129 (7)	0.0009 (6)	0.0039 (6)	0.0019 (6)
C7	0.0134 (7)	0.0127 (7)	0.0164 (7)	−0.0005 (6)	0.0037 (6)	0.0022 (5)
Fe1	0.00899 (9)	0.01107 (9)	0.01090 (9)	−0.00018 (9)	0.00159 (6)	−0.00057 (8)
C8	0.0130 (6)	0.0346 (10)	0.0122 (6)	−0.0008 (8)	0.0035 (5)	−0.0002 (8)
C9	0.0137 (8)	0.0218 (8)	0.0187 (8)	−0.0011 (7)	0.0036 (6)	0.0071 (7)
C10	0.0122 (8)	0.0152 (7)	0.0206 (8)	−0.0031 (6)	0.0012 (6)	0.0016 (6)
C11	0.0092 (7)	0.0175 (7)	0.0188 (7)	0.0016 (6)	0.0007 (6)	0.0012 (6)
C12	0.0156 (9)	0.0218 (8)	0.0234 (9)	−0.0003 (7)	0.0091 (7)	−0.0071 (7)

Geometric parameters (Å, º) top

Cl1—C1	1.7741 (17)	C7—Fe1	2.0434 (17)
C1—C2	1.517 (2)	C7—H7	0.9500
C1—H1A	0.9900	Fe1—C10	2.0426 (18)
C1—H1B	0.9900	Fe1—C8	2.0487 (15)
C2—O1	1.220 (2)	Fe1—C11	2.0491 (19)
C2—C3	1.471 (2)	Fe1—C9	2.0508 (19)
C3—C7	1.437 (2)	Fe1—C12	2.0555 (19)
C3—C4	1.439 (2)	C8—C9	1.424 (3)
C3—Fe1	2.0284 (16)	C8—C12	1.430 (3)
C4—C5	1.430 (3)	C8—H8	0.9500
C4—Fe1	2.0357 (17)	C9—C10	1.427 (3)
C4—H4	0.9500	C9—H9	0.9500
C5—C6	1.431 (2)	C10—C11	1.426 (3)
C5—Fe1	2.0631 (19)	C10—H10	0.9500
C5—H5	0.9500	C11—C12	1.430 (3)
C6—C7	1.421 (3)	C11—H11	0.9500
C6—Fe1	2.0604 (19)	C12—H12	0.9500
C6—H6	0.9500

C2—C1—Cl1	112.47 (12)	C7—Fe1—C9	163.52 (7)
C2—C1—H1A	109.1	C8—Fe1—C9	40.65 (9)
Cl1—C1—H1A	109.1	C11—Fe1—C9	68.67 (8)
C2—C1—H1B	109.1	C3—Fe1—C12	120.81 (7)
Cl1—C1—H1B	109.1	C4—Fe1—C12	155.48 (8)
H1A—C1—H1B	107.8	C10—Fe1—C12	68.61 (8)
O1—C2—C3	122.05 (16)	C7—Fe1—C12	108.26 (8)
O1—C2—C1	122.61 (16)	C8—Fe1—C12	40.77 (9)
C3—C2—C1	115.32 (14)	C11—Fe1—C12	40.79 (8)
C7—C3—C4	108.32 (14)	C9—Fe1—C12	68.62 (9)
C7—C3—C2	123.89 (14)	C3—Fe1—C6	68.65 (7)
C4—C3—C2	127.55 (15)	C4—Fe1—C6	68.92 (8)
C7—C3—Fe1	69.90 (10)	C10—Fe1—C6	119.73 (8)
C4—C3—Fe1	69.53 (9)	C7—Fe1—C6	40.53 (7)
C2—C3—Fe1	121.95 (11)	C8—Fe1—C6	163.83 (8)
C5—C4—C3	107.29 (15)	C11—Fe1—C6	107.73 (8)
C5—C4—Fe1	70.61 (11)	C9—Fe1—C6	154.25 (8)
C3—C4—Fe1	68.99 (9)	C12—Fe1—C6	126.31 (9)
C5—C4—H4	126.4	C3—Fe1—C5	68.78 (7)
C3—C4—H4	126.4	C4—Fe1—C5	40.84 (8)
Fe1—C4—H4	125.6	C10—Fe1—C5	106.55 (8)
C4—C5—C6	108.22 (17)	C7—Fe1—C5	68.67 (7)
C4—C5—Fe1	68.55 (10)	C8—Fe1—C5	154.42 (9)
C6—C5—Fe1	69.60 (12)	C11—Fe1—C5	125.02 (8)
C4—C5—H5	125.9	C9—Fe1—C5	119.18 (8)
C6—C5—H5	125.9	C12—Fe1—C5	162.89 (8)
Fe1—C5—H5	127.5	C6—Fe1—C5	40.60 (7)
C7—C6—C5	108.61 (18)	C9—C8—C12	108.40 (15)
C7—C6—Fe1	69.09 (10)	C9—C8—Fe1	69.75 (10)
C5—C6—Fe1	69.80 (12)	C12—C8—Fe1	69.87 (10)
C7—C6—H6	125.7	C9—C8—H8	125.8
C5—C6—H6	125.7	C12—C8—H8	125.8
Fe1—C6—H6	127.0	Fe1—C8—H8	126.2
C6—C7—C3	107.55 (15)	C8—C9—C10	107.72 (17)
C6—C7—Fe1	70.38 (11)	C8—C9—Fe1	69.60 (10)
C3—C7—Fe1	68.78 (9)	C10—C9—Fe1	69.30 (10)
C6—C7—H7	126.2	C8—C9—H9	126.1
C3—C7—H7	126.2	C10—C9—H9	126.1
Fe1—C7—H7	126.2	Fe1—C9—H9	126.5
C3—Fe1—C4	41.48 (7)	C11—C10—C9	108.32 (18)
C3—Fe1—C10	162.20 (7)	C11—C10—Fe1	69.85 (12)
C4—Fe1—C10	123.89 (8)	C9—C10—Fe1	69.91 (11)
C3—Fe1—C7	41.32 (7)	C11—C10—H10	125.8
C4—Fe1—C7	69.72 (8)	C9—C10—H10	125.8
C10—Fe1—C7	154.67 (7)	Fe1—C10—H10	126.0
C3—Fe1—C8	107.88 (7)	C10—C11—C12	107.91 (17)
C4—Fe1—C8	119.67 (8)	C10—C11—Fe1	69.36 (11)
C10—Fe1—C8	68.48 (8)	C12—C11—Fe1	69.85 (11)
C7—Fe1—C8	126.57 (8)	C10—C11—H11	126.0
C3—Fe1—C11	155.78 (8)	C12—C11—H11	126.0
C4—Fe1—C11	161.59 (7)	Fe1—C11—H11	126.3
C10—Fe1—C11	40.79 (9)	C8—C12—C11	107.64 (17)
C7—Fe1—C11	120.28 (7)	C8—C12—Fe1	69.36 (10)
C8—Fe1—C11	68.57 (7)	C11—C12—Fe1	69.37 (11)
C3—Fe1—C9	125.21 (7)	C8—C12—H12	126.2
C4—Fe1—C9	106.05 (8)	C11—C12—H12	126.2
C10—Fe1—C9	40.79 (7)	Fe1—C12—H12	126.7

Cl1—C1—C2—O1	4.3 (2)	C5—C6—C7—Fe1	−58.76 (16)
Cl1—C1—C2—C3	−177.38 (12)	C4—C3—C7—C6	−0.9 (2)
O1—C2—C3—C7	−6.7 (3)	C2—C3—C7—C6	−175.62 (16)
C1—C2—C3—C7	174.94 (16)	Fe1—C3—C7—C6	−59.96 (13)
O1—C2—C3—C4	179.58 (18)	C4—C3—C7—Fe1	59.10 (12)
C1—C2—C3—C4	1.2 (2)	C2—C3—C7—Fe1	−115.66 (16)
O1—C2—C3—Fe1	−92.74 (19)	C12—C8—C9—C10	0.4 (2)
C1—C2—C3—Fe1	88.90 (16)	Fe1—C8—C9—C10	−59.01 (13)
C7—C3—C4—C5	1.19 (19)	C12—C8—C9—Fe1	59.38 (13)
C2—C3—C4—C5	175.70 (17)	C8—C9—C10—C11	−0.3 (2)
Fe1—C3—C4—C5	60.52 (13)	Fe1—C9—C10—C11	−59.50 (14)
C7—C3—C4—Fe1	−59.33 (12)	C8—C9—C10—Fe1	59.20 (12)
C2—C3—C4—Fe1	115.18 (17)	C9—C10—C11—C12	0.1 (2)
C3—C4—C5—C6	−1.1 (2)	Fe1—C10—C11—C12	−59.42 (14)
Fe1—C4—C5—C6	58.42 (16)	C9—C10—C11—Fe1	59.54 (13)
C3—C4—C5—Fe1	−59.49 (12)	C9—C8—C12—C11	−0.3 (2)
C4—C5—C6—C7	0.5 (3)	Fe1—C8—C12—C11	59.01 (13)
Fe1—C5—C6—C7	58.33 (15)	C9—C8—C12—Fe1	−59.31 (12)
C4—C5—C6—Fe1	−57.78 (14)	C10—C11—C12—C8	0.1 (2)
C5—C6—C7—C3	0.2 (2)	Fe1—C11—C12—C8	−59.01 (13)
Fe1—C6—C7—C3	58.95 (12)	C10—C11—C12—Fe1	59.12 (14)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C8–C12 Cp ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cl1ⁱ	0.95	2.88	3.4196 (19)	117
C1—H1B···O1ⁱⁱ	0.99	2.30	3.256 (2)	163
C9—H9···Cl1ⁱⁱ	0.95	2.95	3.841 (2)	157
C9—H9···O1ⁱⁱ	0.95	2.56	3.262 (2)	131
C1—H1A···Cg2ⁱⁱⁱ	0.99	2.69	3.4383 (18)	132

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

Acknowledgements

We thank the NZ Ministry of Business, Innovation and Employment Science Investment Fund (grant No. UOO-X1206) for support of this work and the University of Otago for the purchase of the diffractometer and support of the work of JS.

References

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Volume 1| Part 1| January 2016| x152177

https://doi.org/10.1107/S241431461502177X

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Chloro-1-ferrocenyl­ethanone

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

metal-organic compounds

2-Chloro-1-ferrocenylethanone