Di­chloro­maleic anhydride

Blake, A.J.; Griffiths, R.M.T.; Howdle, S.M.; Wilson, C.

doi:10.1107/S0108270100007034

Dichloromaleic anhydride

A. J. Blake, R. M. T. Griffiths, S. M. Howdle and C. Wilson

Although molecules of the title compound, 3,4-dichloro-2,5-dihydrofuran-2,5-dione (dichloromaleic anhydride, C₄Cl₂O₃), (I), possess approximate non-crystallographic C_2v symmetry, the two chlorine substituents deviate from the ring plane. Their deviations are in the same direction, but with values of 0.0356 (17) and 0.0167 (17) Å, they differ significantly in magnitude. The closest intermolecular contact is of 2.888 (2) Å between a carbonyl O atom and the C atom of a carbonyl group, with the O

C direction orthogonal to the C=O bond [O5

C2ⁱ=O2ⁱ 93.6 (2)°; symmetry code: (i) $3 \over 2$ - x, -½ + y, z]. These contacts form infinite chains of molecules running parallel to the crystallographic b direction.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007034/qa0304sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007034/qa0304Isup2.hkl Contains datablock I

CCDC reference: 146107

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1999).

(I) top

Crystal data top

C₄Cl₂O₃	F(000) = 656
M_r = 166.94	D_x = 1.941 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5130 reflections
a = 10.6397 (6) Å	θ = 3.1–28.6°
b = 8.2558 (5) Å	µ = 1.05 mm⁻¹
c = 13.0057 (7) Å	T = 150 K
V = 1142.41 (11) Å³	Block, colourless
Z = 8	0.32 × 0.32 × 0.25 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1372 independent reflections
Radiation source: fine-focus sealed tube	1261 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ω scans	θ_max = 28.6°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 1996)	h = 0→14
T_min = 0.730, T_max = 0.779	k = 0→11
7980 measured reflections	l = 0→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.041P)² + 0.34P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.023	(Δ/σ)_max = 0.001
wR(F²) = 0.067	Δρ_max = 0.35 e Å⁻³
S = 1.04	Δρ_min = −0.21 e Å⁻³
1372 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
83 parameters	Extinction coefficient: 0.0056 (7)
0 restraints

Special details top

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.8224 (0.0054) x + 6.8975 (0.0028) y - 0.6529 (0.0066) z = 4.1943 (0.0036)

* -0.0007 (0.0006) O1 * 0.0023 (0.0006) C2 * -0.0031 (0.0007) C3 * 0.0028 (0.0007) C4 * -0.0012 (0.0006) C5 - 0.0039 (0.0017) O2 - 0.0023 (0.0018) O5 - 0.0356 (0.0017) Cl3 - 0.0167 (0.0017) Cl4

Rms deviation of fitted atoms = 0.0022 ___________________________________________________________________

Short Non-Hydrogen Inter-Molecular Contacts

Contact-Nr Atom I [ARU] Atom J [ARU] d(I—J) Del ——————————————————————- 1 O(2) [1555.01] ··· C(4) [4655.01] = 3.019 - 0.20 2 O(2) [1555.01] ··· C(5) [4655.01] = 3.011 - 0.21 3 O(5) [1555.01] ··· C(2) [7645.01] = 2.888 - 0.33

[4655.01] = 1 - x,1/2 + y,1/2 - z [7645.01] = 3/2 - x,-1/2 + y,z

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
O1	0.62393 (8)	0.09767 (10)	0.17283 (6)	0.0261 (2)
C2	0.53423 (10)	0.17933 (13)	0.23110 (9)	0.0241 (2)
O2	0.44778 (10)	0.24782 (10)	0.19319 (8)	0.0319 (2)
C3	0.56901 (11)	0.15962 (13)	0.34126 (9)	0.0232 (2)
Cl3	0.48172 (3)	0.23767 (4)	0.43703 (3)	0.03491 (12)
C4	0.67404 (10)	0.07227 (13)	0.34605 (8)	0.0223 (2)
Cl4	0.75628 (3)	0.00979 (4)	0.44921 (2)	0.03129 (12)
C5	0.71187 (11)	0.02966 (14)	0.23941 (9)	0.0235 (2)
O5	0.79899 (9)	−0.04691 (11)	0.20904 (7)	0.0310 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0300 (4)	0.0266 (4)	0.0217 (4)	0.0028 (3)	−0.0014 (3)	−0.0012 (3)
C2	0.0239 (5)	0.0197 (5)	0.0287 (6)	−0.0025 (4)	0.0006 (4)	−0.0003 (4)
O2	0.0264 (5)	0.0297 (5)	0.0397 (6)	0.0017 (3)	−0.0057 (4)	0.0047 (4)
C3	0.0244 (5)	0.0210 (5)	0.0241 (5)	−0.0036 (4)	0.0034 (4)	−0.0017 (4)
Cl3	0.0336 (2)	0.0363 (2)	0.0348 (2)	−0.00032 (12)	0.01382 (12)	−0.00629 (12)
C4	0.0235 (5)	0.0226 (5)	0.0209 (5)	−0.0039 (4)	−0.0003 (4)	0.0011 (4)
Cl4	0.03173 (19)	0.0370 (2)	0.02518 (19)	−0.00352 (12)	−0.00609 (11)	0.00644 (11)
C5	0.0250 (5)	0.0203 (5)	0.0253 (6)	−0.0020 (4)	−0.0001 (4)	−0.0001 (4)
O5	0.0303 (5)	0.0299 (4)	0.0327 (5)	0.0060 (4)	0.0050 (4)	−0.0028 (4)

Geometric parameters (Å, º) top

O1—C2	1.3927 (14)	C3—Cl3	1.6820 (12)
O1—C5	1.3929 (14)	C4—C5	1.4864 (16)
C2—O2	1.1870 (15)	C4—Cl4	1.6829 (11)
C2—C3	1.4886 (16)	C5—O5	1.1895 (15)
C3—C4	1.3314 (17)

C2—O1—C5	108.49 (9)	C3—C4—C5	108.17 (10)
O2—C2—O1	122.39 (11)	C3—C4—Cl4	129.77 (9)
O2—C2—C3	130.13 (11)	C5—C4—Cl4	122.05 (9)
O1—C2—C3	107.48 (9)	O5—C5—O1	122.09 (11)
C4—C3—C2	108.23 (10)	O5—C5—C4	130.29 (11)
C4—C3—Cl3	129.51 (9)	O1—C5—C4	107.62 (10)
C2—C3—Cl3	122.25 (9)

C5—O1—C2—O2	−179.59 (11)	C2—C3—C4—Cl4	−179.23 (9)
C5—O1—C2—C3	−0.27 (11)	Cl3—C3—C4—Cl4	−0.15 (18)
O2—C2—C3—C4	179.77 (12)	C2—O1—C5—O5	−179.93 (11)
O1—C2—C3—C4	0.53 (13)	C2—O1—C5—C4	−0.05 (11)
O2—C2—C3—Cl3	0.61 (18)	C3—C4—C5—O5	−179.74 (13)
O1—C2—C3—Cl3	−178.63 (7)	Cl4—C4—C5—O5	−0.94 (18)
C2—C3—C4—C5	−0.55 (13)	C3—C4—C5—O1	0.39 (12)
Cl3—C3—C4—C5	178.53 (9)	Cl4—C4—C5—O1	179.19 (8)

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

Di­chloro­maleic anhydride

Supporting information

Dichloromaleic anhydride