2,3,5,6-Tetra­chloro-1,4-di­cyano­benzene–anthracene (1/1)

2,3,5,6-Tetra­chloro-1,4-di­cyano­benzene forms a 1:1 complex with anthracene, C₈N₂Cl₄·C₁₄H₁₀. The two mol­ecules, which both lie on inversion centers, alternate in π stacks. There are no unusual intermolecular interactions.

Key indicators

• Single-crystal X-ray study
• T = 174 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.121
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.31
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.21
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C7     ...       1.45 Ang.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.13 Ratio

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

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

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2,3,5,6-tetrachlorodicyanobenzene–anthracene (1/1)

Crystal data

C8N2Cl4·C14H10	Z = 1
Mr = 444.12	F(000) = 224
Triclinic, P1	Dx = 1.544 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.294 (2) Å	Cell parameters from 3062 reflections
b = 8.762 (2) Å	θ = 2.6–27.4°
c = 8.891 (2) Å	µ = 0.63 mm^−1
α = 64.87 (1)°	T = 174 K
β = 70.10 (1)°	Prism, yellow
γ = 73.79 (1)°	0.45 × 0.40 × 0.35 mm
V = 477.6 (2) Å^3

Data collection

Siemens area-detector diffractometer	2143 independent reflections
Radiation source: fine-focus sealed tube	1739 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω scans	θmax = 27.6°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995)	h = −9→9
Tmin = 0.77, Tmax = 0.80	k = −11→11
5418 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	All H-atom parameters refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.086P)^2] where P = (Fo^2 + 2Fc^2)/3
2143 reflections	(Δ/σ)max = 0.005
147 parameters	Δρmax = 0.48 e Å^−3
0 restraints	Δρmin = −0.60 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.0833 (3)	0.8297 (2)	0.5658 (2)	0.0243 (4)
C2	0.0149 (3)	0.9261 (2)	0.6709 (2)	0.0243 (4)
C6	0.0685 (3)	0.9033 (2)	0.3960 (2)	0.0254 (4)
C7	0.1684 (3)	0.6514 (3)	0.6338 (3)	0.0311 (4)
N1	0.2350 (3)	0.5115 (2)	0.6870 (3)	0.0450 (5)
Cl2	0.03328 (7)	0.83383 (6)	0.87908 (6)	0.03240 (18)
Cl6	0.15288 (9)	0.78139 (7)	0.27055 (7)	0.0412 (2)
C11	0.4995 (3)	0.0483 (2)	0.3263 (2)	0.0244 (4)
C12	0.4967 (3)	0.1025 (3)	0.1518 (3)	0.0326 (5)
H12	0.552 (3)	0.019 (3)	0.096 (3)	0.036 (6)*
C13	0.4125 (3)	0.2645 (3)	0.0680 (3)	0.0387 (5)
H13	0.414 (4)	0.290 (4)	−0.042 (4)	0.056 (8)*
C14	0.3274 (3)	0.3801 (3)	0.1535 (3)	0.0391 (5)
H14	0.272 (4)	0.501 (4)	0.085 (4)	0.057 (8)*
C15	0.3298 (3)	0.3357 (3)	0.3181 (3)	0.0332 (5)
H15	0.284 (3)	0.413 (4)	0.378 (3)	0.046 (7)*
C16	0.4161 (3)	0.1671 (2)	0.4129 (2)	0.0253 (4)
C17	0.4183 (3)	0.1172 (2)	0.5835 (3)	0.0266 (4)
H17	0.369 (3)	0.195 (3)	0.636 (3)	0.031 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0249 (9)	0.0167 (9)	0.0262 (9)	−0.0013 (7)	−0.0108 (8)	−0.0010 (7)
C2	0.0250 (9)	0.0193 (9)	0.0229 (9)	−0.0035 (7)	−0.0103 (7)	0.0007 (7)
C6	0.0274 (9)	0.0202 (9)	0.0259 (9)	−0.0013 (7)	−0.0080 (8)	−0.0065 (7)
C7	0.0362 (10)	0.0188 (10)	0.0321 (10)	0.0014 (8)	−0.0147 (8)	−0.0026 (8)
N1	0.0583 (13)	0.0247 (10)	0.0443 (11)	0.0049 (9)	−0.0242 (10)	−0.0041 (8)
Cl2	0.0391 (3)	0.0288 (3)	0.0236 (3)	−0.0040 (2)	−0.0154 (2)	0.0005 (2)
Cl6	0.0606 (4)	0.0264 (3)	0.0335 (3)	0.0047 (2)	−0.0157 (3)	−0.0125 (2)
C11	0.0252 (9)	0.0200 (9)	0.0250 (9)	−0.0058 (7)	−0.0093 (7)	−0.0019 (7)
C12	0.0329 (10)	0.0364 (12)	0.0259 (10)	−0.0095 (9)	−0.0095 (8)	−0.0048 (9)
C13	0.0362 (11)	0.0431 (13)	0.0270 (10)	−0.0145 (10)	−0.0151 (9)	0.0068 (9)
C14	0.0348 (11)	0.0253 (11)	0.0405 (12)	−0.0077 (9)	−0.0171 (10)	0.0110 (9)
C15	0.0348 (10)	0.0161 (10)	0.0399 (12)	−0.0014 (8)	−0.0141 (9)	−0.0003 (8)
C16	0.0245 (9)	0.0159 (9)	0.0289 (10)	−0.0029 (7)	−0.0104 (8)	0.0004 (7)
C17	0.0303 (10)	0.0186 (9)	0.0300 (10)	−0.0014 (7)	−0.0098 (8)	−0.0081 (8)

Geometric parameters (Å, º)

C1—C6	1.397 (3)	C12—C13	1.369 (3)
C1—C2	1.398 (3)	C12—H12	0.98 (2)
C1—C7	1.450 (2)	C13—C14	1.404 (4)
C2—C6^i	1.394 (3)	C13—H13	0.90 (3)
C2—Cl2	1.7129 (19)	C14—C15	1.351 (3)
C6—C2^i	1.394 (3)	C14—H14	1.02 (3)
C6—Cl6	1.7147 (19)	C15—C16	1.440 (3)
C7—N1	1.137 (3)	C15—H15	0.96 (3)
C11—C17^ii	1.400 (3)	C16—C17	1.393 (3)
C11—C12	1.423 (3)	C17—C11^ii	1.400 (3)
C11—C16	1.434 (3)	C17—H17	0.91 (2)
C6—C1—C2	120.51 (17)	C12—C13—C14	120.3 (2)
C6—C1—C7	119.64 (17)	C12—C13—H13	116.4 (18)
C2—C1—C7	119.85 (17)	C14—C13—H13	123.3 (18)
C6^i—C2—C1	119.05 (17)	C15—C14—C13	121.1 (2)
C6^i—C2—Cl2	120.99 (15)	C15—C14—H14	121.0 (15)
C1—C2—Cl2	119.95 (14)	C13—C14—H14	117.8 (15)
C2^i—C6—C1	120.44 (17)	C14—C15—C16	121.1 (2)
C2^i—C6—Cl6	120.17 (15)	C14—C15—H15	123.9 (16)
C1—C6—Cl6	119.39 (15)	C16—C15—H15	114.9 (16)
N1—C7—C1	179.9 (2)	C17—C16—C11	120.02 (17)
C17^ii—C11—C12	122.27 (18)	C17—C16—C15	122.34 (19)
C17^ii—C11—C16	118.71 (17)	C11—C16—C15	117.63 (18)
C12—C11—C16	119.02 (17)	C16—C17—C11^ii	121.27 (18)
C13—C12—C11	120.8 (2)	C16—C17—H17	119.6 (15)
C13—C12—H12	121.4 (15)	C11^ii—C17—H17	119.1 (15)
C11—C12—H12	117.7 (15)

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