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A high-resolution X-ray diffraction measurement of 2,5-di­chloro-1,4-benzo­quinone (DCBQ) at 20 K was carried out. The experimental charge density was modeled using the Hansen–Coppens multipolar expansion and the topology of the electron density was analyzed in terms of the quantum theory of atoms in molecules (QTAIM). Two different multipole models, predominantly differentiated by the treatment of the chlorine atom, were obtained. The experimental results have been compared to theoretical results in the form of a multipolar refinement against theoretical structure factors and through direct topological analysis of the electron density obtained from the optimized periodic wavefunction. The similarity of the properties of the total electron density in all cases demonstrates the robustness of the Hansen–Coppens formalism. All intra- and intermolecular interactions have been characterized.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520617007363/lc5082sup1.cif
Contains datablocks global, Model_1, Model_2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617007363/lc5082Model_1sup2.hkl
Contains datablock Model_1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617007363/lc5082Model_2sup3.hkl
Contains datablock Model_2

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520617007363/lc5082sup4.pdf
Supporting figures and tables

CCDC references: 1550937; 1550938

Computing details top

For both structures, data collection: CrystalClear, (2005); cell refinement: Otwinowski & Minor (1997); data reduction: Zhurova et al.,(1999), Zhurov et al.,(2008), Blessing, (1995,1997); program(s) used to solve structure: Sheldrick (2008); program(s) used to refine structure: Volkov et al., (2006); molecular graphics: Volkov et al., (2006), Stash, (2002,2005); software used to prepare material for publication: Volkov et al., (2006).

(Model_1) top
Crystal data top
C6H2Cl2O2F(000) = 176
Mr = 176.98Dx = 1.852 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.0246 (1) ÅCell parameters from 50012 reflections
b = 5.3112 (2) Åθ = 3.4–70.9°
c = 9.9258 (3) ŵ = 0.94 mm1
β = 92.585 (3)°T = 20 K
V = 317.28 (2) Å3Block, colourless
Z = 20.25 × 0.21 × 0.15 mm
Data collection top
Rigaku R-axis Rapid
diffractometer
Rint = 0.012
w scansθmax = 70.9°
50012 measured reflectionsh = 1515
6041 independent reflectionsk = 013
5464 reflections with I > 3σ, nonoverlapped & nonpartial reflectionsl = 026
Refinement top
Refinement on FH atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0024P)2 + 0.0063P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.008(Δ/σ)max < 0.001
wR(F2) = 0.007Δρmax = 0.19 e Å3
S = 1.95Δρmin = 0.21 e Å3
5464 reflectionsExtinction correction: Becker-Coppens type 1 Lorentzian isotropic, Becker, P.J. & Coppens, P. (1974) Acta Cryst., A30, 129-153.
241 parametersExtinction coefficient: 0.0090 (8)
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
CL(1)0.414997 (2)0.266682 (3)0.866303 (1)0.006
O(1)0.152959 (12)0.706218 (16)0.777334 (8)0.008
C(1)0.188671 (4)0.384324 (5)0.943392 (3)0.006
C(2)0.082172 (4)0.611856 (5)0.879242 (3)0.006
C(3)0.111499 (4)0.280415 (6)1.055484 (3)0.006
H(1)0.1905460.1173851.1015990.018
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
CL(1)0.005614 (6)0.007663 (8)0.006016 (7)0.001166 (4)0.001601 (4)0.000222 (4)
O(1)0.00870 (2)0.00872 (3)0.00639 (2)0.00016 (3)0.00266 (2)0.00212 (2)
C(1)0.005537 (6)0.006108 (9)0.005376 (7)0.000654 (5)0.001396 (5)0.000377 (6)
C(2)0.005726 (6)0.005909 (9)0.005103 (7)0.000195 (5)0.001375 (5)0.000600 (6)
C(3)0.006587 (6)0.006715 (9)0.005765 (7)0.001253 (6)0.001721 (5)0.001172 (6)
H(1)0.0229 (7)0.0173 (6)0.0151 (7)0.0087 (5)0.0041 (5)0.0050 (5)
Geometric parameters (Å, º) top
CL(1)—C(1)1.7115 (1)C(1)—C(3)1.3436 (1)
O(1)—C(2)1.2228 (3)C(2)—C(3)i1.4754 (1)
C(1)—C(2)1.4969 (1)C(3)—H(1)1.0800 (1)
CL(1)—C(1)—C(2)116.066 (6)C(1)—C(2)—C(3)i117.296 (7)
CL(1)—C(1)—C(3)122.186 (7)C(1)—C(3)—C(2)i120.957 (8)
C(2)—C(1)—C(3)121.746 (8)C(1)—C(3)—H(1)121.187 (8)
O(1)—C(2)—C(1)121.601 (14)C(2)i—C(3)—H(1)117.849 (8)
O(1)—C(2)—C(3)i121.102 (15)
Symmetry code: (i) x, y+1, z+2.
(Model_2) top
Crystal data top
C6H2Cl2O2F(000) = 176
Mr = 176.98Dx = 1.852 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.0246 (1) ÅCell parameters from 50012 reflections
b = 5.3112 (2) Åθ = 3.4–70.9°
c = 9.9258 (3) ŵ = 0.94 mm1
β = 92.585 (3)°T = 20 K
V = 317.28 (2) Å3Block, colourless
Z = 20.25 × 0.21 × 0.15 mm
Data collection top
Rigaku R-axis Rapid
diffractometer
Rint = 0.012
w scansθmax = 70.9°
50012 measured reflectionsh = 1515
6041 independent reflectionsk = 013
5464 reflections with I > 3σ, nonoverlapped & nonpartial reflectionsl = 026
Refinement top
Refinement on FH atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0023P)2 + 0.0061P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.008(Δ/σ)max < 0.001
wR(F2) = 0.007Δρmax = 0.20 e Å3
S = 1.89Δρmin = 0.21 e Å3
5464 reflectionsExtinction correction: Becker-Coppens type 1 Lorentzian isotropic, Becker, P.J. & Coppens, P. (1974) Acta Cryst., A30, 129-153.
244 parametersExtinction coefficient: 0.0138 (3)
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
CL(1)0.415011 (1)0.266677 (1)0.866292 (1)0.006
O(1)0.152974 (4)0.706209 (5)0.777328 (3)0.008
C(1)0.188701 (1)0.384300 (2)0.943381 (1)0.006
C(2)0.082178 (1)0.611856 (2)0.879239 (1)0.006
C(3)0.111504 (1)0.280408 (2)1.055485 (1)0.006
H(1)0.1890280.1162281.1013290.019
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
CL(1)0.005744 (3)0.007545 (3)0.005970 (3)0.001096 (2)0.001504 (2)0.000151 (2)
O(1)0.008675 (8)0.008707 (10)0.006377 (8)0.000168 (9)0.002665 (7)0.002162 (7)
C(1)0.005545 (2)0.006075 (3)0.005351 (2)0.000641 (2)0.001371 (2)0.000395 (2)
C(2)0.005722 (2)0.005903 (3)0.005099 (2)0.000199 (2)0.001376 (2)0.000599 (2)
C(3)0.006577 (2)0.006720 (3)0.005760 (2)0.001257 (2)0.001728 (2)0.001172 (2)
H(1)0.0222 (2)0.0173 (2)0.0167 (2)0.00848 (15)0.00408 (16)0.00541 (15)
Geometric parameters (Å, º) top
CL(1)—C(1)1.7114 (1)C(1)—C(3)1.3437 (1)
O(1)—C(2)1.2228 (3)C(2)—C(3)i1.4755 (1)
C(1)—C(2)1.4970 (1)C(3)—H(1)1.0800 (1)
CL(1)—C(1)—C(2)116.069 (6)C(1)—C(2)—C(3)i117.303 (7)
CL(1)—C(1)—C(3)122.196 (7)C(1)—C(3)—C(2)i120.964 (8)
C(2)—C(1)—C(3)121.733 (7)C(1)—C(3)—H(1)121.413 (8)
O(1)—C(2)—C(1)121.591 (14)C(2)i—C(3)—H(1)117.623 (8)
O(1)—C(2)—C(3)i121.105 (15)
Symmetry code: (i) x, y+1, z+2.
 

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