1-(3,4-Dichloro­benzo­yl)ferrocene

Erben, M.; Růžička, A.; Vinklárek, J.; Šťáva, V.; Veselý, D.

doi:10.1107/S1600536807053391

1-(3,4-Dichlorobenzoyl)ferrocene

M. Erben, A. Růžička, J. Vinklárek, V. Šťáva and D. Veselý

In the title compound, [Fe(C₅H₅)(C₁₂H₇Cl₂O)], the cyclopentadienyl rings are almost parallel and eclipsed as typically found for similar monosubstituted ferrocene derivatives. Weak C—H

O and C—H

Cl hydrogen bonds link molecules into two-dimensional layers parallel to the ac plane in the crystal structure.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053391/bh2140sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053391/bh2140Isup2.hkl Contains datablock I

CCDC reference: 672696

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.005 Å
R factor = 0.042
wR factor = 0.101
Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.133
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Fe1         (3)       3.79

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Ferrocene complexes are widely used in homogenous catalysis, organic or organometallic synthesis and in material science. The use of ferrocene and its derivatives as catalyst in drying process of oxidizable paints was investigated recently (Šťáva et al., 2007) and it was observed that ferrocenes bearing electron-withdrawing substituents show the highest activity. As a part of our investigation of ferrocene derivatives, we have prepared the title compound, (I), and determined its structure in the solid state.

As Figure 1 shows, the title compound displays a structure typical for monosubstituted acylferrocenes. The cyclopentadienyl (Cp) rings are almost parallel, making a dihedral angle of 2.0 (2)°, and are eclipsed as viewed down the normal of Cp rings. The dihedral angle between a ring C atom, the two ring centroids and the C atom of opposite ring varies from 3.1 (2)° to 3.9 (3)°. The interatomic distances and angles in (I) are very close to those found in benzoylferrocene (Butler et al., 1988), see Table 1.

The angle between the plane defined by ring of 3,4-dichlorobenzoyl group and Cp ring bonded to this group is found to be 39.5 (2)°, validating that Cp and benzene ring π-systems are not conjugated. Carbonyl atom C11 is displaced slightly out of the Cp ring away from the Fe atom, with an angle of 1.3 (2)° between the ring plane and C1—C11 bond.

Geometric parameters of weak intermolecular interactions observed in the crystal of (I) are listed in the Table 2. Atom O1 of the molecule at (-1 + x, 1 - y, z) serves as an acceptor for atom C17 of the molecule in the asymmetric unit, generating molecular wires along the [100] axis. Atom C9 of the asymmetric unit serves as a donor to atom Cl2 of the molecule at (-1 + x, y, 1 + z), linking the above mentioned molecular wires into two-dimensional layers parallel to the ac plane.

Related literature top

The title complex has been synthesized following a procedure described by Reeves (1977). For related literature dealing with the crystal structures of related ferrocenyl complexes formulated as FeCp(C₅H₄COAr), where Cp = η⁵-C₅H₅ and Ar = C₆H₅, 4-C₆H₄CH₃, 4-C₆H₄NH₂ and 4-C₆H₄OH, see: Butler et al. (1988); Figueroa et al. (2005); Bényei et al. (1997). For the use of derivatives similar to the title complex as catalyst in drying process of oxidizable paints, see: Šťáva et al. (2007).

Experimental top

The title compound was synthesized from ferrocene and 3,4-dichlorobenzoyl chloride in the presence of AlCl₃ following the procedure described by Reeves (1977). Melting point, IR and NMR spectra confirmed identity and purity of prepared compound. Crystals suitable for X-ray diffraction analysis were grown by sublimation in a sealed ampoule at 0.1 Pa and 380 K.

Computing details top

Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); data reduction: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Figures top

Fig. 1. ORTEP view of the title compound with displacement ellipsoids drawn at the 50% probability level.

1-(3,4-Dichlorobenzoyl)ferrocene top

Crystal data top

[Fe(C₅H₅)(C₁₂H₇Cl₂O)]	Z = 2
M_r = 359.02	F(000) = 364
Triclinic, P1	D_x = 1.719 Mg m⁻³
Hall symbol: -P 1	Melting point: 426 K
a = 6.1970 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0720 (5) Å	Cell parameters from 11119 reflections
c = 11.8160 (7) Å	θ = 1–27.5°
α = 78.098 (4)°	µ = 1.47 mm⁻¹
β = 76.452 (4)°	T = 150 K
γ = 78.903 (3)°	Plate, red
V = 693.47 (6) Å³	0.40 × 0.30 × 0.06 mm

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	3169 independent reflections
Radiation source: fine-focus sealed tube	2773 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.133
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ϕ and ω scans to fill the Ewald sphere	h = −7→8
Absorption correction: integration Gaussian integration (Coppens et al., 1970)	k = −13→12
T_min = 0.551, T_max = 0.916	l = −15→15
11098 measured reflections

Refinement top

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) = 0.102	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0055P)² + 0.7487P] where P = (F_o² + 2F_c²)/3
3169 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.72 e Å⁻³
0 restraints	Δρ_min = −0.74 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₂H₇Cl₂O)]	γ = 78.903 (3)°
M_r = 359.02	V = 693.47 (6) Å³
Triclinic, P1	Z = 2
a = 6.1970 (3) Å	Mo Kα radiation
b = 10.0720 (5) Å	µ = 1.47 mm⁻¹
c = 11.8160 (7) Å	T = 150 K
α = 78.098 (4)°	0.40 × 0.30 × 0.06 mm
β = 76.452 (4)°

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	3169 independent reflections
Absorption correction: integration Gaussian integration (Coppens et al., 1970)	2773 reflections with I > 2σ(I)
T_min = 0.551, T_max = 0.916	R_int = 0.133
11098 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.15	Δρ_max = 0.72 e Å⁻³
3169 reflections	Δρ_min = −0.74 e Å⁻³
190 parameters

Special details top

Experimental. Melting point: 426–427 K. Spectroscopic analysis: ¹H NMR (benzene-d₆, δ, p.p.m.): 3.84 (s, 5H), 4.09 (m, 2H), 4.66 (m, 2H), 6.95 (m, 1H), 7.44 (m, 1H), 8.04 (d, 1H). ¹³C NMR (benzene-d₆, δ, p.p.m.): 67.0, 71.1, 72.3, 77.8, 129.5, 130.2, 132.3, 135.4, 139.3, 184.5. Uv-Vis (cyclohexane, maxima at nm): 473, 369, 284 (sh). IR (KBr disc, cm^-1): 3108 (m), 1625 (s), 1581 (m), 1555 (m), 1533 (w), 1455 (m), 1445 (s), 1385 (s), 1289 (s), 1246 (m), 1172 (m), 1131 (w), 1106 (m), 1054 (m), 1028 (m), 1002 (w), 969 (m), 907 (m), 877 (w), 848 (w), 829 (s), 767 (m), 752 (m), 678 (m), 667 (w), 579 (w), 538 (m), 501 (m), 486 (m), 442 (w).

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

	x	y	z	U_iso*/U_eq
Fe1	0.83358 (6)	0.22818 (4)	0.27185 (4)	0.01123 (12)
Cl2	0.33933 (12)	0.18553 (8)	0.93854 (7)	0.02494 (19)
Cl1	0.76392 (12)	0.31674 (8)	0.92710 (7)	0.02464 (19)
O1	1.1551 (3)	0.3333 (3)	0.4841 (2)	0.0256 (5)
C4	0.9628 (5)	0.3893 (3)	0.1563 (3)	0.0178 (6)
H4	1.0332	0.3891	0.0776	0.021*
C13	0.8399 (4)	0.3279 (3)	0.6918 (3)	0.0138 (6)
H13	0.9690	0.3638	0.6888	0.017*
C1	0.9018 (4)	0.3649 (3)	0.3600 (3)	0.0133 (6)
C15	0.5085 (4)	0.2371 (3)	0.8039 (3)	0.0138 (6)
C16	0.4526 (4)	0.2223 (3)	0.7020 (3)	0.0149 (6)
H16	0.3223	0.1873	0.7056	0.018*
C7	0.6071 (5)	0.0945 (3)	0.3417 (3)	0.0181 (6)
H7	0.4651	0.1143	0.3879	0.022*
C11	0.9590 (4)	0.3365 (3)	0.4761 (3)	0.0149 (6)
C14	0.6996 (4)	0.2925 (3)	0.7995 (3)	0.0140 (6)
C12	0.7887 (4)	0.3099 (3)	0.5885 (3)	0.0129 (6)
C17	0.5904 (4)	0.2596 (3)	0.5934 (3)	0.0139 (6)
H17	0.5513	0.2512	0.5241	0.017*
C5	1.0691 (5)	0.3524 (3)	0.2539 (3)	0.0173 (6)
H5	1.2222	0.3245	0.2502	0.021*
C10	0.9866 (5)	0.0274 (3)	0.2838 (3)	0.0198 (7)
H10	1.1371	−0.0044	0.2858	0.024*
C2	0.6896 (4)	0.4111 (3)	0.3241 (3)	0.0153 (6)
H2	0.5507	0.4278	0.3740	0.018*
C9	0.8939 (5)	0.0678 (3)	0.1809 (3)	0.0191 (6)
H9	0.9731	0.0672	0.1037	0.023*
C8	0.6603 (5)	0.1094 (3)	0.2159 (3)	0.0181 (6)
H8	0.5591	0.1410	0.1657	0.022*
C3	0.7291 (5)	0.4269 (3)	0.1992 (3)	0.0186 (6)
H3	0.6206	0.4568	0.1531	0.022*
C6	0.8093 (5)	0.0440 (3)	0.3838 (3)	0.0198 (7)
H6	0.8235	0.0252	0.4624	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0107 (2)	0.00976 (18)	0.0112 (2)	−0.00165 (14)	0.00060 (14)	−0.00050 (15)
Cl2	0.0214 (4)	0.0346 (4)	0.0160 (4)	−0.0112 (3)	0.0055 (3)	−0.0020 (3)
Cl1	0.0274 (4)	0.0353 (4)	0.0144 (4)	−0.0120 (3)	−0.0057 (3)	−0.0030 (3)
O1	0.0101 (9)	0.0460 (14)	0.0210 (14)	−0.0065 (9)	−0.0018 (8)	−0.0056 (11)
C4	0.0257 (14)	0.0134 (12)	0.0114 (16)	−0.0076 (11)	0.0017 (11)	0.0025 (11)
C13	0.0099 (11)	0.0157 (12)	0.0152 (16)	−0.0029 (10)	−0.0030 (10)	−0.0001 (11)
C1	0.0139 (12)	0.0111 (12)	0.0138 (16)	−0.0039 (10)	0.0005 (10)	−0.0015 (11)
C15	0.0117 (12)	0.0131 (12)	0.0140 (16)	−0.0013 (10)	0.0015 (10)	−0.0017 (11)
C16	0.0104 (12)	0.0154 (12)	0.0182 (17)	−0.0022 (10)	−0.0019 (10)	−0.0023 (11)
C7	0.0173 (13)	0.0173 (13)	0.0197 (17)	−0.0099 (11)	0.0000 (11)	−0.0009 (12)
C11	0.0120 (12)	0.0155 (12)	0.0171 (16)	−0.0025 (10)	−0.0027 (11)	−0.0023 (11)
C14	0.0153 (12)	0.0147 (12)	0.0125 (16)	−0.0006 (10)	−0.0057 (10)	−0.0020 (11)
C12	0.0103 (12)	0.0122 (12)	0.0137 (16)	0.0001 (10)	−0.0009 (10)	0.0002 (10)
C17	0.0099 (11)	0.0163 (12)	0.0155 (16)	−0.0012 (10)	−0.0028 (10)	−0.0034 (11)
C5	0.0158 (13)	0.0180 (13)	0.0163 (16)	−0.0069 (11)	0.0039 (11)	−0.0029 (11)
C10	0.0189 (13)	0.0099 (12)	0.027 (2)	0.0023 (10)	−0.0034 (12)	−0.0010 (12)
C2	0.0149 (12)	0.0089 (11)	0.0212 (17)	0.0003 (10)	−0.0038 (11)	−0.0020 (11)
C9	0.0263 (15)	0.0162 (13)	0.0133 (16)	−0.0060 (12)	0.0045 (12)	−0.0065 (11)
C8	0.0225 (14)	0.0163 (13)	0.0173 (17)	−0.0063 (11)	−0.0053 (11)	−0.0020 (12)
C3	0.0228 (14)	0.0115 (12)	0.0203 (18)	−0.0002 (11)	−0.0054 (12)	−0.0009 (11)
C6	0.0271 (15)	0.0122 (12)	0.0182 (17)	−0.0069 (11)	−0.0023 (12)	0.0025 (12)

Geometric parameters (Å, º) top

Fe1—C2	2.037 (3)	C15—C16	1.372 (4)
Fe1—C8	2.043 (3)	C15—C14	1.390 (4)
Fe1—C1	2.045 (3)	C16—C17	1.389 (4)
Fe1—C5	2.046 (3)	C16—H16	0.9300
Fe1—C7	2.047 (2)	C7—C6	1.421 (4)
Fe1—C9	2.049 (3)	C7—C8	1.428 (5)
Fe1—C4	2.053 (2)	C7—H7	0.9300
Fe1—C6	2.053 (3)	C11—C12	1.502 (4)
Fe1—C10	2.053 (3)	C12—C17	1.402 (3)
Fe1—C3	2.053 (3)	C17—H17	0.9300
Cl2—C15	1.728 (3)	C5—H5	0.9300
Cl1—C14	1.720 (3)	C10—C9	1.417 (5)
O1—C11	1.235 (3)	C10—C6	1.426 (4)
C4—C5	1.409 (4)	C10—H10	0.9300
C4—C3	1.422 (4)	C2—C3	1.419 (5)
C4—H4	0.9300	C2—H2	0.9300
C13—C12	1.384 (4)	C9—C8	1.414 (4)
C13—C14	1.385 (4)	C9—H9	0.9300
C13—H13	0.9300	C8—H8	0.9300
C1—C5	1.439 (4)	C3—H3	0.9300
C1—C2	1.439 (4)	C6—H6	0.9300
C1—C11	1.454 (4)

C2—Fe1—C8	122.72 (11)	C15—C16—C17	120.0 (2)
C2—Fe1—C1	41.27 (11)	C15—C16—H16	120.0
C8—Fe1—C1	160.73 (11)	C17—C16—H16	120.0
C2—Fe1—C5	68.79 (11)	C6—C7—C8	108.0 (3)
C8—Fe1—C5	155.61 (13)	C6—C7—Fe1	69.95 (14)
C1—Fe1—C5	41.17 (11)	C8—C7—Fe1	69.44 (14)
C2—Fe1—C7	107.01 (11)	C6—C7—H7	126.0
C8—Fe1—C7	40.86 (12)	C8—C7—H7	126.0
C1—Fe1—C7	124.75 (12)	Fe1—C7—H7	126.2
C5—Fe1—C7	162.75 (13)	O1—C11—C1	119.5 (3)
C2—Fe1—C9	159.04 (13)	O1—C11—C12	117.7 (3)
C8—Fe1—C9	40.44 (12)	C1—C11—C12	122.8 (2)
C1—Fe1—C9	158.00 (12)	C13—C14—C15	119.7 (3)
C5—Fe1—C9	121.68 (12)	C13—C14—Cl1	119.8 (2)
C7—Fe1—C9	68.28 (12)	C15—C14—Cl1	120.5 (2)
C2—Fe1—C4	68.58 (12)	C13—C12—C17	119.6 (3)
C8—Fe1—C4	119.76 (13)	C13—C12—C11	117.6 (2)
C1—Fe1—C4	68.83 (12)	C17—C12—C11	122.7 (3)
C5—Fe1—C4	40.22 (12)	C16—C17—C12	119.8 (3)
C7—Fe1—C4	155.46 (13)	C16—C17—H17	120.1
C9—Fe1—C4	106.74 (12)	C12—C17—H17	120.1
C2—Fe1—C6	122.28 (13)	C4—C5—C1	108.8 (2)
C8—Fe1—C6	68.47 (12)	C4—C5—Fe1	70.13 (15)
C1—Fe1—C6	108.89 (12)	C1—C5—Fe1	69.37 (14)
C5—Fe1—C6	126.45 (12)	C4—C5—H5	125.6
C7—Fe1—C6	40.56 (12)	C1—C5—H5	125.6
C9—Fe1—C6	68.30 (13)	Fe1—C5—H5	126.5
C4—Fe1—C6	162.02 (12)	C9—C10—C6	108.2 (3)
C2—Fe1—C10	158.73 (14)	C9—C10—Fe1	69.63 (16)
C8—Fe1—C10	68.11 (12)	C6—C10—Fe1	69.67 (16)
C1—Fe1—C10	123.20 (12)	C9—C10—H10	125.9
C5—Fe1—C10	109.30 (12)	C6—C10—H10	125.9
C7—Fe1—C10	68.18 (11)	Fe1—C10—H10	126.4
C9—Fe1—C10	40.41 (13)	C3—C2—C1	108.1 (2)
C4—Fe1—C10	124.55 (12)	C3—C2—Fe1	70.31 (17)
C6—Fe1—C10	40.65 (12)	C1—C2—Fe1	69.65 (16)
C2—Fe1—C3	40.58 (13)	C3—C2—H2	125.9
C8—Fe1—C3	105.76 (12)	C1—C2—H2	125.9
C1—Fe1—C3	68.74 (12)	Fe1—C2—H2	125.7
C5—Fe1—C3	67.95 (12)	C8—C9—C10	108.2 (3)
C7—Fe1—C3	120.48 (11)	C8—C9—Fe1	69.58 (17)
C9—Fe1—C3	122.75 (14)	C10—C9—Fe1	69.96 (18)
C4—Fe1—C3	40.52 (11)	C8—C9—H9	125.9
C6—Fe1—C3	156.78 (12)	C10—C9—H9	125.9
C10—Fe1—C3	159.99 (14)	Fe1—C9—H9	126.2
C5—C4—C3	108.0 (3)	C9—C8—C7	108.0 (3)
C5—C4—Fe1	69.65 (15)	C9—C8—Fe1	69.98 (16)
C3—C4—Fe1	69.76 (14)	C7—C8—Fe1	69.70 (16)
C5—C4—H4	126.0	C9—C8—H8	126.0
C3—C4—H4	126.0	C7—C8—H8	126.0
Fe1—C4—H4	126.2	Fe1—C8—H8	125.9
C12—C13—C14	120.2 (2)	C2—C3—C4	108.4 (3)
C12—C13—H13	119.9	C2—C3—Fe1	69.11 (16)
C14—C13—H13	119.9	C4—C3—Fe1	69.72 (15)
C5—C1—C2	106.6 (3)	C2—C3—H3	125.8
C5—C1—C11	122.2 (2)	C4—C3—H3	125.8
C2—C1—C11	131.2 (3)	Fe1—C3—H3	127.0
C5—C1—Fe1	69.46 (17)	C7—C6—C10	107.6 (3)
C2—C1—Fe1	69.07 (16)	C7—C6—Fe1	69.49 (15)
C11—C1—Fe1	127.36 (18)	C10—C6—Fe1	69.68 (15)
C16—C15—C14	120.6 (3)	C7—C6—H6	126.2
C16—C15—Cl2	119.39 (19)	C10—C6—H6	126.2
C14—C15—Cl2	120.0 (2)	Fe1—C6—H6	126.2

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₂H₇Cl₂O)]
M_r	359.02
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	6.1970 (3), 10.0720 (5), 11.8160 (7)
α, β, γ (°)	78.098 (4), 76.452 (4), 78.903 (3)
V (Å³)	693.47 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.47
Crystal size (mm)	0.40 × 0.30 × 0.06

Data collection
Diffractometer	Bruker–Nonius KappaCCD area-detector diffractometer
Absorption correction	Integration Gaussian integration (Coppens et al., 1970)
T_min, T_max	0.551, 0.916
No. of measured, independent and observed [I > 2σ(I)] reflections	11098, 3169, 2773
R_int	0.133
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.102, 1.15
No. of reflections	3169
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.74

Computer programs: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), enCIFer (Allen et al., 2004).

Selected geometric parameters (Å, °) top

Fe1···Cg1	1.6505 (10)
Fe1···Cg2	1.6479 (10)

Cg1···Fe1···Cg2	177.94 (8)

Cg1 and Cg2 are the centroids defined by atoms C1–C5 and C6–C10, respectively.

Hydrogen-bond geometry (Å, °) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O1ⁱ	0.93	2.56	3.156 (4)	123
C9—H9···Cl2ⁱⁱ	0.93	2.90	3.658 (3)	140

Symmetry codes: (i) x - 1, -y + 1, z; (ii) x - 1, y, z + 1.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

1-(3,4-Dichloro­benzo­yl)ferrocene

Supporting information

Key indicators

checkCIF/PLATON results

1-(3,4-Dichlorobenzoyl)ferrocene