Planar packing of tetrachlorodicyanobenzene isomers

Ortho-, meta- and para-tetrachlorodicyanobenzene (TBD, tetrachlorobenzenedicarbonitrile) form 1/1 complexes with hexamethylbenzene (HMB). Seven polymorphic forms of the crystals, one of o-TDB, two of m-TDB and four of p-TBD, have been found. All of the complexes involve layers of two-dimensional arrays, and in six of the complexes the layers are homogeneous, alternate layers being entirely TDB or entirely HMB. The layers can be described in terms of an hexagonal tiling and in five of the homogeneous layers the TDB are ordered so that one CN and two Cl come together at each corner of the tiles. In the sixth the m-TDB is disordered, but a plausible arrangement can still be found with one CN and two Cl coming together in the same fashion.

Computing details

Data collection: SMART for ortho, metaI, metaII, paraII, paraIII, paraIV; CAD-4 Software for paraI. Cell refinement: SAINT for ortho, metaI, metaII, paraII, paraIII, paraIV; CAD-4 Software for paraI. Data reduction: SAINT for ortho, metaI, metaII, paraII, paraIII, paraIV; TEXSAN for paraI. Program(s) used to solve structure: TEXSAN, MITHRIL, DIRDIF for ortho, paraI, paraII, paraIII; TEXSAN, MITHRIL, DIRDIF, SHELXTL (Sheldrick, 1994) for metaI; SHELXTL (Sheldrick, 1994) for metaII, paraIV. Program(s) used to refine structure: SHELXTL (Sheldrick, 1994) for ortho, metaI, paraI, paraII, paraIII; SHELXTL for metaII, paraIV. Molecular graphics: TEXSAN, SHELXTL for ortho, paraI, paraII, paraIII; SHELXTL for metaI, metaII, paraIV.

(ortho) ortho tetrachlorodicyanobenzene/hexamethyl benzene, 1/1

Crystal data

C12H18·C8Cl4N2	F(000) = 880
Mr = 428.16	Dx = 1.450 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.824 (3) Å	Cell parameters from 1872 reflections
b = 9.1501 (15) Å	θ = 3–27°
c = 13.894 (2) Å	µ = 0.61 mm^−1
β = 102.879 (3)°	T = 173 K
V = 1961.1 (6) Å^3	Needle, yellow
Z = 4	0.45 × 0.15 × 0.10 mm

Data collection

Siemens SMART area-detector diffractometer	2242 independent reflections
Radiation source: fine-focus sealed tube	1604 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995	h = −18→20
Tmin = 0.90, Tmax = 0.94	k = −11→11
6155 measured reflections	l = −16→18

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) = 0.113	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.062P)^2] where P = (Fo^2 + 2Fc^2)/3
2242 reflections	(Δ/σ)max = 0.004
121 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl5	0.59865 (4)	0.96463 (6)	0.25827 (5)	0.0452 (2)
Cl6	0.69849 (4)	0.67011 (6)	0.26371 (5)	0.04175 (19)
N1	0.62706 (13)	0.29419 (19)	0.26325 (15)	0.0387 (5)
C1	0.54454 (13)	0.5385 (2)	0.25327 (15)	0.0262 (4)
C5	0.54438 (15)	0.8025 (2)	0.25328 (16)	0.0301 (5)
C6	0.58908 (14)	0.6707 (2)	0.25629 (15)	0.0283 (5)
C7	0.59078 (13)	0.4013 (2)	0.25794 (15)	0.0275 (4)
C11	0.58932 (16)	0.5064 (3)	0.00754 (16)	0.0410 (6)
C12	0.54047 (18)	0.6352 (2)	−0.00111 (17)	0.0417 (6)
C13	0.45132 (17)	0.6284 (3)	−0.00753 (16)	0.0418 (6)
C21	0.68711 (18)	0.5135 (4)	0.0165 (2)	0.0701 (9)
H21A	0.7155	0.4379	0.0624	0.105*
H21B	0.7086	0.6099	0.0413	0.105*
H21C	0.7000	0.4972	−0.0485	0.105*
C22	0.5841 (3)	0.7822 (3)	−0.0039 (2)	0.0686 (9)
H22A	0.6358	0.7701	−0.0309	0.103*
H22B	0.6008	0.8219	0.0631	0.103*
H22C	0.5437	0.8495	−0.0458	0.103*
C23	0.3979 (2)	0.7673 (3)	−0.0147 (2)	0.0646 (9)
H23A	0.3471	0.7501	0.0133	0.097*
H23B	0.3788	0.7960	−0.0841	0.097*
H23C	0.4332	0.8456	0.0222	0.097*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl5	0.0586 (4)	0.0247 (3)	0.0538 (4)	−0.0143 (3)	0.0154 (3)	−0.0018 (2)
Cl6	0.0284 (3)	0.0431 (3)	0.0551 (4)	−0.0071 (2)	0.0123 (3)	−0.0017 (3)
N1	0.0373 (11)	0.0297 (11)	0.0510 (13)	0.0036 (8)	0.0141 (10)	0.0011 (9)
C1	0.0294 (10)	0.0226 (10)	0.0279 (11)	0.0025 (8)	0.0089 (9)	−0.0006 (8)
C5	0.0388 (12)	0.0223 (10)	0.0292 (11)	−0.0040 (8)	0.0078 (10)	−0.0014 (8)
C6	0.0279 (11)	0.0289 (11)	0.0289 (11)	−0.0046 (8)	0.0080 (9)	−0.0005 (9)
C7	0.0250 (10)	0.0274 (11)	0.0311 (11)	−0.0011 (9)	0.0082 (9)	0.0011 (9)
C11	0.0463 (14)	0.0499 (15)	0.0263 (12)	0.0080 (12)	0.0073 (10)	−0.0014 (10)
C12	0.0608 (16)	0.0358 (12)	0.0287 (12)	0.0007 (12)	0.0107 (11)	−0.0006 (10)
C13	0.0595 (16)	0.0380 (13)	0.0268 (12)	0.0173 (12)	0.0072 (11)	0.0020 (10)
C21	0.0526 (18)	0.102 (3)	0.0548 (19)	0.0031 (18)	0.0108 (15)	−0.0107 (17)
C22	0.107 (3)	0.0497 (16)	0.0547 (18)	−0.0216 (18)	0.0307 (18)	−0.0040 (14)
C23	0.092 (2)	0.0535 (17)	0.0475 (16)	0.0383 (17)	0.0135 (16)	0.0023 (13)

Geometric parameters (Å, º)

Cl5—C5	1.708 (2)	C12—C22	1.516 (4)
Cl6—C6	1.711 (2)	C13—C11^ii	1.391 (3)
N1—C7	1.130 (3)	C13—C23	1.518 (3)
C1—C1^i	1.392 (4)	C21—H21A	0.9800
C1—C6	1.396 (3)	C21—H21B	0.9800
C1—C7	1.448 (3)	C21—H21C	0.9800
C5—C5^i	1.387 (5)	C22—H22A	0.9800
C5—C6	1.394 (3)	C22—H22B	0.9800
C11—C13^ii	1.391 (3)	C22—H22C	0.9800
C11—C12	1.399 (3)	C23—H23A	0.9800
C11—C21	1.526 (4)	C23—H23B	0.9800
C12—C13	1.395 (4)	C23—H23C	0.9800
C1^i—C1—C6	119.94 (12)	C11—C21—H21A	109.5
C1^i—C1—C7	119.82 (11)	C11—C21—H21B	109.5
C6—C1—C7	120.24 (18)	H21A—C21—H21B	109.5
C5^i—C5—C6	120.11 (12)	C11—C21—H21C	109.5
C5^i—C5—Cl5	119.69 (8)	H21A—C21—H21C	109.5
C6—C5—Cl5	120.20 (17)	H21B—C21—H21C	109.5
C5—C6—C1	119.95 (19)	C12—C22—H22A	109.5
C5—C6—Cl6	120.30 (16)	C12—C22—H22B	109.5
C1—C6—Cl6	119.75 (16)	H22A—C22—H22B	109.5
N1—C7—C1	178.8 (2)	C12—C22—H22C	109.5
C13^ii—C11—C12	120.0 (2)	H22A—C22—H22C	109.5
C13^ii—C11—C21	119.8 (2)	H22B—C22—H22C	109.5
C12—C11—C21	120.1 (2)	C13—C23—H23A	109.5
C13—C12—C11	120.0 (2)	C13—C23—H23B	109.5
C13—C12—C22	119.8 (2)	H23A—C23—H23B	109.5
C11—C12—C22	120.2 (3)	C13—C23—H23C	109.5
C11^ii—C13—C12	120.0 (2)	H23A—C23—H23C	109.5
C11^ii—C13—C23	119.5 (2)	H23B—C23—H23C	109.5
C12—C13—C23	120.5 (2)

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

(metaI) meta tetrachlorodicyanobenzene/hexamethylbenzene, 1/1 polymorph I

Crystal data

C12H18·C8Cl4N2	Z = 1
Mr = 428.16	F(000) = 220
Triclinic, P1	Dx = 1.473 Mg m^−3
a = 7.5290 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9503 (14) Å	Cell parameters from 776 reflections
c = 9.0513 (11) Å	θ = 2.7–27.4°
α = 118.425 (3)°	µ = 0.62 mm^−1
β = 109.414 (3)°	T = 173 K
γ = 95.139 (3)°	Thick plate, pale yellow
V = 482.80 (12) Å^3	0.50 × 0.35 × 0.10 mm

Data collection

Siemens SMART area-detectcor diffractometer	2197 independent reflections
Radiation source: fine-focus sealed tube	1784 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995	h = −9→9
Tmin = 0.76, Tmax = 0.94	k = −11→11
4996 measured reflections	l = −11→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.072P)^2 + 0.059P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.006
2197 reflections	Δρmax = 0.27 e Å^−3
185 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.037 (8)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl12	0.50548 (16)	−0.20864 (14)	0.15855 (14)	0.0379 (3)	0.50
Cl14	0.47371 (12)	−0.13216 (12)	−0.40184 (12)	0.0339 (2)	0.50
Cl15	0.49291 (15)	0.26965 (13)	−0.16595 (15)	0.0368 (3)	0.50
Cl16	0.51453 (19)	0.42166 (19)	0.23267 (16)	0.0364 (3)	0.50
N11	0.5341 (4)	0.2301 (4)	0.5055 (4)	0.0427 (6)	0.50
N13	0.4777 (7)	−0.4770 (6)	−0.2992 (5)	0.0405 (10)	0.50
C1	0.5105 (6)	0.1009 (7)	0.1736 (7)	0.0260 (9)	0.50
C2	0.5011 (6)	−0.0772 (6)	0.0674 (6)	0.0288 (8)	0.50
C3	0.4934 (6)	−0.1476 (6)	−0.1105 (7)	0.0263 (9)	0.50
C4	0.4908 (6)	−0.0414 (5)	−0.1812 (6)	0.0225 (8)	0.50
C5	0.4971 (5)	0.1357 (5)	−0.0776 (5)	0.0240 (7)	0.50
C6	0.5054 (6)	0.2039 (5)	0.1000 (6)	0.0237 (8)	0.50
C11	0.5214 (5)	0.1771 (4)	0.3620 (5)	0.0300 (7)	0.50
C13	0.4853 (4)	−0.3316 (6)	−0.2180 (4)	0.0321 (7)	0.50
C21	−0.0011 (2)	0.11360 (19)	−0.0659 (2)	0.0348 (3)
C22	−0.01445 (19)	−0.06584 (19)	−0.18044 (18)	0.0337 (3)
C23	−0.01234 (19)	−0.17907 (18)	−0.11388 (19)	0.0337 (3)
C31	−0.0033 (3)	0.2354 (2)	−0.1391 (3)	0.0482 (4)
H31A	−0.0632	0.1636	−0.2753	0.072*	0.50
H31B	0.1322	0.3056	−0.0926	0.072*	0.50
H31C	−0.0804	0.3157	−0.0965	0.072*	0.50
H31D	0.0556	0.3597	−0.0343	0.072*	0.50
H31E	−0.1398	0.2176	−0.2170	0.072*	0.50
H31F	0.0728	0.2076	−0.2130	0.072*	0.50
C32	−0.0315 (3)	−0.1357 (2)	−0.3753 (2)	0.0475 (4)
H32A	−0.0726	−0.0539	−0.4133	0.071*	0.50
H32B	−0.1297	−0.2535	−0.4618	0.071*	0.50
H32C	0.0967	−0.1450	−0.3767	0.071*	0.50
H32D	0.0022	−0.2477	−0.4212	0.071*	0.50
H32E	0.0593	−0.0481	−0.3728	0.071*	0.50
H32F	−0.1671	−0.1566	−0.4578	0.071*	0.50
C33	−0.0273 (3)	−0.3734 (2)	−0.2370 (2)	0.0486 (4)
H33A	−0.0736	−0.4060	−0.3662	0.073*	0.50
H33B	−0.1208	−0.4487	−0.2281	0.073*	0.50
H33C	0.1027	−0.3906	−0.1960	0.073*	0.50
H33D	0.0125	−0.4242	−0.1606	0.073*	0.50
H33E	0.0597	−0.3815	−0.2987	0.073*	0.50
H33F	−0.1638	−0.4396	−0.3309	0.073*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl12	0.0483 (5)	0.0393 (6)	0.0347 (4)	0.0147 (4)	0.0202 (3)	0.0241 (5)
Cl14	0.0416 (4)	0.0363 (5)	0.0219 (4)	0.0119 (3)	0.0173 (3)	0.0120 (4)
Cl15	0.0485 (5)	0.0367 (6)	0.0352 (4)	0.0166 (4)	0.0222 (3)	0.0228 (4)
Cl16	0.0447 (5)	0.0318 (8)	0.0295 (6)	0.0131 (5)	0.0175 (5)	0.0130 (5)
N11	0.0494 (16)	0.0443 (15)	0.0329 (14)	0.0141 (12)	0.0170 (12)	0.0201 (13)
N13	0.0492 (18)	0.035 (2)	0.039 (2)	0.0136 (18)	0.022 (2)	0.0187 (19)
C1	0.0263 (14)	0.023 (2)	0.0261 (17)	0.0056 (16)	0.0109 (11)	0.0123 (18)
C2	0.0296 (15)	0.033 (2)	0.0312 (18)	0.0114 (14)	0.0132 (11)	0.0219 (19)
C3	0.0318 (16)	0.025 (2)	0.0262 (17)	0.0109 (17)	0.0140 (12)	0.0147 (19)
C4	0.0229 (13)	0.023 (2)	0.0178 (14)	0.0040 (15)	0.0101 (9)	0.0075 (18)
C5	0.0262 (14)	0.029 (2)	0.0211 (14)	0.0098 (13)	0.0112 (10)	0.0156 (15)
C6	0.0243 (13)	0.023 (2)	0.0192 (15)	0.0079 (15)	0.0098 (10)	0.0073 (17)
C11	0.0310 (15)	0.0335 (16)	0.0337 (18)	0.0094 (11)	0.0157 (13)	0.0228 (14)
C13	0.0365 (16)	0.0340 (19)	0.0352 (19)	0.0140 (13)	0.0174 (12)	0.0232 (19)
C21	0.0277 (7)	0.0425 (7)	0.0333 (7)	0.0097 (5)	0.0125 (6)	0.0203 (6)
C22	0.0239 (7)	0.0433 (7)	0.0245 (6)	0.0062 (5)	0.0086 (5)	0.0135 (6)
C23	0.0262 (7)	0.0350 (7)	0.0297 (7)	0.0073 (5)	0.0108 (5)	0.0114 (6)
C31	0.0495 (10)	0.0578 (10)	0.0520 (10)	0.0213 (8)	0.0256 (8)	0.0364 (9)
C32	0.0463 (9)	0.0584 (10)	0.0288 (7)	0.0092 (7)	0.0176 (7)	0.0172 (7)
C33	0.0479 (9)	0.0400 (8)	0.0453 (9)	0.0126 (7)	0.0207 (8)	0.0138 (7)

Geometric parameters (Å, º)

Cl12—C2	1.726 (4)	C23—C33	1.521 (2)
Cl14—C4	1.712 (4)	C31—H31A	0.9800
Cl15—C5	1.726 (4)	C31—H31B	0.9800
Cl16—C6	1.714 (4)	C31—H31C	0.9800
N11—C11	1.115 (4)	C31—H31D	0.9800
N13—C13	1.134 (5)	C31—H31E	0.9800
C1—C6	1.367 (5)	C31—H31F	0.9800
C1—C2	1.395 (6)	C32—H32A	0.9800
C1—C11	1.473 (6)	C32—H32B	0.9800
C2—C3	1.400 (6)	C32—H32C	0.9800
C3—C4	1.374 (5)	C32—H32D	0.9800
C3—C13	1.442 (6)	C32—H32E	0.9800
C4—C5	1.391 (5)	C32—H32F	0.9800
C5—C6	1.398 (6)	C33—H33A	0.9800
C21—C23^i	1.405 (2)	C33—H33B	0.9800
C21—C22	1.408 (2)	C33—H33C	0.9800
C21—C31	1.520 (2)	C33—H33D	0.9800
C22—C23	1.403 (2)	C33—H33E	0.9800
C22—C32	1.5180 (19)	C33—H33F	0.9800
C23—C21^i	1.405 (2)
C6—C1—C2	119.4 (4)	H31B—C31—H31F	56.3
C6—C1—C11	120.0 (4)	H31C—C31—H31F	141.1
C2—C1—C11	120.5 (4)	H31D—C31—H31F	109.5
C1—C2—C3	120.1 (3)	H31E—C31—H31F	109.5
C1—C2—Cl12	119.8 (3)	C22—C32—H32A	109.5
C3—C2—Cl12	120.2 (4)	C22—C32—H32B	109.5
C4—C3—C2	119.6 (4)	H32A—C32—H32B	109.5
C4—C3—C13	121.0 (4)	C22—C32—H32C	109.5
C2—C3—C13	119.4 (4)	H32A—C32—H32C	109.5
C3—C4—C5	120.8 (4)	H32B—C32—H32C	109.5
C3—C4—Cl14	118.8 (3)	C22—C32—H32D	109.5
C5—C4—Cl14	120.4 (3)	H32A—C32—H32D	141.1
C4—C5—C6	118.8 (4)	H32B—C32—H32D	56.3
C4—C5—Cl15	121.1 (3)	H32C—C32—H32D	56.3
C6—C5—Cl15	120.2 (3)	C22—C32—H32E	109.5
C1—C6—C5	121.3 (4)	H32A—C32—H32E	56.3
C1—C6—Cl16	118.5 (4)	H32B—C32—H32E	141.1
C5—C6—Cl16	120.3 (3)	H32C—C32—H32E	56.3
N11—C11—C1	177.0 (4)	H32D—C32—H32E	109.5
N13—C13—C3	178.1 (4)	C22—C32—H32F	109.5
C23^i—C21—C22	120.23 (13)	H32A—C32—H32F	56.3
C23^i—C21—C31	120.32 (13)	H32B—C32—H32F	56.3
C22—C21—C31	119.45 (13)	H32C—C32—H32F	141.1
C23—C22—C21	119.79 (13)	H32D—C32—H32F	109.5
C23—C22—C32	120.41 (13)	H32E—C32—H32F	109.5
C21—C22—C32	119.80 (14)	C23—C33—H33A	109.5
C22—C23—C21^i	119.98 (12)	C23—C33—H33B	109.5
C22—C23—C33	120.12 (14)	H33A—C33—H33B	109.5
C21^i—C23—C33	119.90 (14)	C23—C33—H33C	109.5
C21—C31—H31A	109.5	H33A—C33—H33C	109.5
C21—C31—H31B	109.5	H33B—C33—H33C	109.5
H31A—C31—H31B	109.5	C23—C33—H33D	109.5
C21—C31—H31C	109.5	H33A—C33—H33D	141.1
H31A—C31—H31C	109.5	H33B—C33—H33D	56.3
H31B—C31—H31C	109.5	H33C—C33—H33D	56.3
C21—C31—H31D	109.5	C23—C33—H33E	109.5
H31A—C31—H31D	141.1	H33A—C33—H33E	56.3
H31B—C31—H31D	56.3	H33B—C33—H33E	141.1
H31C—C31—H31D	56.3	H33C—C33—H33E	56.3
C21—C31—H31E	109.5	H33D—C33—H33E	109.5
H31A—C31—H31E	56.3	C23—C33—H33F	109.5
H31B—C31—H31E	141.1	H33A—C33—H33F	56.3
H31C—C31—H31E	56.3	H33B—C33—H33F	56.3
H31D—C31—H31E	109.5	H33C—C33—H33F	141.1
C21—C31—H31F	109.5	H33D—C33—H33F	109.5
H31A—C31—H31F	56.3	H33E—C33—H33F	109.5

Symmetry code: (i) −x, −y, −z.

(metaII) meta tetrachlorodicyanobenzene/hexamethylbenzene, 1/1 polymorph II

Crystal data

C12H18·C8Cl4N2	Z = 4
Mr = 428.16	F(000) = 880
Triclinic, P1	Dx = 1.467 Mg m^−3
a = 14.064 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9554 (13) Å	Cell parameters from 3897 reflections
c = 18.117 (3) Å	θ = 2.7–27.2°
α = 118.407 (2)°	µ = 0.62 mm^−1
β = 90.832 (3)°	T = 173 K
γ = 76.460 (2)°	Prism, yellow
V = 1938.8 (5) Å^3	0.45 × 0.40 × 0.35 mm

Data collection

Bruker SMART area-detector diffractometer	8698 independent reflections
Radiation source: fine-focus sealed tube	5502 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
ω scans	θmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995	h = −18→18
Tmin = 0.76, Tmax = 0.81	k = −11→11
19454 measured reflections	l = −23→23

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.225	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.153P)^2] where P = (Fo^2 + 2Fc^2)/3
8698 reflections	(Δ/σ)max = 0.027
542 parameters	Δρmax = 1.27 e Å^−3
90 restraints	Δρmin = −0.63 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.24599 (19)	0.6544 (4)	0.79039 (15)	0.0183 (6)	0.8152 (10)
C2	0.24893 (19)	0.8288 (4)	0.84144 (16)	0.0200 (6)	0.8152 (10)
C3	0.25340 (19)	0.8939 (4)	0.92836 (15)	0.0192 (6)	0.8152 (10)
C4	0.25543 (18)	0.7852 (3)	0.96332 (15)	0.0181 (6)	0.8152 (10)
C5	0.25143 (18)	0.6114 (3)	0.91319 (16)	0.0182 (6)	0.8152 (10)
C6	0.24747 (18)	0.5468 (3)	0.82642 (16)	0.0183 (6)	0.8152 (10)
C7	0.2400 (3)	0.5856 (4)	0.6998 (2)	0.0292 (4)	0.8152 (10)
N1	0.23299 (18)	0.5372 (3)	0.63054 (14)	0.0292 (4)	0.8152 (10)
C8	0.2575 (2)	1.0755 (4)	0.98001 (18)	0.0295 (4)	0.8152 (10)
N3	0.2588 (2)	1.2182 (4)	1.01995 (15)	0.0295 (4)	0.8152 (10)
Cl2	0.24703 (6)	0.96139 (11)	0.79734 (5)	0.0301 (2)	0.8152 (10)
Cl4	0.26309 (5)	0.86870 (9)	1.06968 (4)	0.0258 (2)	0.8152 (10)
Cl5	0.25386 (6)	0.47643 (10)	0.95599 (5)	0.0281 (2)	0.8152 (10)
Cl6	0.24281 (6)	0.33431 (10)	0.76188 (4)	0.0270 (2)	0.8152 (10)
C11	0.25474 (19)	0.8451 (4)	0.45970 (16)	0.0195 (6)	0.8152 (10)
C12	0.25131 (19)	0.6706 (3)	0.40866 (16)	0.0195 (6)	0.8152 (10)
C13	0.24700 (19)	0.6054 (4)	0.32222 (16)	0.0201 (6)	0.8152 (10)
C14	0.24526 (18)	0.7136 (3)	0.28676 (15)	0.0186 (6)	0.8152 (10)
C15	0.24830 (19)	0.8884 (3)	0.33712 (16)	0.0207 (6)	0.8152 (10)
C16	0.25288 (18)	0.9522 (3)	0.42381 (16)	0.0191 (6)	0.8152 (10)
C17	0.2608 (2)	0.9138 (4)	0.55040 (19)	0.0277 (4)	0.8152 (10)
N11	0.26697 (18)	0.9632 (3)	0.61930 (14)	0.0277 (4)	0.8152 (10)
C18	0.2431 (2)	0.4237 (4)	0.27013 (18)	0.0282 (4)	0.8152 (10)
N13	0.2388 (2)	0.2820 (4)	0.23042 (15)	0.0282 (4)	0.8152 (10)
Cl12	0.25308 (6)	0.53808 (11)	0.45267 (5)	0.0295 (2)	0.8152 (10)
Cl14	0.23688 (5)	0.63075 (9)	0.18031 (4)	0.0261 (2)	0.8152 (10)
Cl15	0.24628 (6)	1.02307 (10)	0.29381 (5)	0.0280 (2)	0.8152 (10)
Cl16	0.25705 (6)	1.16536 (10)	0.48808 (4)	0.0273 (2)	0.8152 (10)
C21	0.00710 (17)	0.1723 (3)	0.05390 (15)	0.0270 (5)
C22	0.00105 (17)	0.1137 (3)	−0.03314 (15)	0.0286 (6)
C23	0.00726 (16)	0.0591 (3)	0.08665 (14)	0.0279 (6)
C31	0.0019 (2)	0.2366 (4)	−0.06808 (18)	0.0413 (7)
H31A	−0.0244	0.3584	−0.0235	0.062*	0.50
H31B	−0.0389	0.2107	−0.1148	0.062*	0.50
H31C	0.0696	0.2205	−0.0886	0.062*	0.50
H31D	0.0286	0.1680	−0.1278	0.062*	0.50
H31E	0.0431	0.3157	−0.0365	0.062*	0.50
H31F	−0.0654	0.3059	−0.0626	0.062*	0.50
C32	0.0159 (2)	0.3577 (4)	0.11135 (17)	0.0425 (7)
H32A	0.0416	0.3654	0.1632	0.064*	0.50
H32B	−0.0491	0.4406	0.1255	0.064*	0.50
H32C	0.0608	0.3870	0.0824	0.064*	0.50
H32D	−0.0061	0.4299	0.0842	0.064*	0.50
H32E	0.0847	0.3547	0.1219	0.064*	0.50
H32F	−0.0252	0.4083	0.1650	0.064*	0.50
C33	0.0155 (2)	0.1202 (4)	0.18001 (16)	0.0412 (7)
H33A	0.0444	0.2209	0.2038	0.062*	0.50
H33B	0.0575	0.0242	0.1865	0.062*	0.50
H33C	−0.0501	0.1550	0.2098	0.062*	0.50
H33D	−0.0099	0.0458	0.1963	0.062*	0.50
H33E	−0.0230	0.2425	0.2135	0.062*	0.50
H33F	0.0847	0.1117	0.1903	0.062*	0.50
C41	0.00526 (17)	0.1732 (3)	0.55381 (15)	0.0272 (5)
C42	−0.00254 (17)	0.1146 (3)	0.46709 (15)	0.0278 (6)
C43	0.00771 (16)	0.0587 (3)	0.58647 (14)	0.0262 (5)
C51	−0.0062 (2)	0.2386 (4)	0.43198 (19)	0.0418 (7)
H51A	0.0262	0.3302	0.4678	0.063*	0.50
H51B	−0.0749	0.2931	0.4310	0.063*	0.50
H51C	0.0278	0.1731	0.3745	0.063*	0.50
H51D	−0.0401	0.2007	0.3810	0.063*	0.50
H51E	0.0610	0.2378	0.4178	0.063*	0.50
H51F	−0.0418	0.3578	0.4743	0.063*	0.50
C52	0.0129 (2)	0.3598 (4)	0.61131 (18)	0.0430 (7)
H52A	0.0387	0.3682	0.6633	0.065*	0.50
H52B	−0.0524	0.4416	0.6253	0.065*	0.50
H52C	0.0574	0.3898	0.5824	0.065*	0.50
H52D	−0.0096	0.4316	0.5840	0.065*	0.50
H52E	0.0816	0.3582	0.6220	0.065*	0.50
H52F	−0.0282	0.4100	0.6649	0.065*	0.50
C53	0.0156 (2)	0.1206 (4)	0.67977 (16)	0.0419 (7)
H53A	0.0304	0.2355	0.7062	0.063*	0.50
H53B	0.0684	0.0357	0.6862	0.063*	0.50
H53C	−0.0469	0.1305	0.7071	0.063*	0.50
H53D	0.0042	0.0323	0.6935	0.063*	0.50
H53E	−0.0338	0.2321	0.7135	0.063*	0.50
H53F	0.0815	0.1373	0.6925	0.063*	0.50
C61	0.49955 (16)	0.6096 (3)	0.21783 (15)	0.0256 (5)
C62	0.50606 (16)	0.6681 (3)	0.30459 (15)	0.0256 (5)
C63	0.50717 (16)	0.5535 (3)	0.33731 (14)	0.0250 (5)
C64	0.50060 (17)	0.3819 (3)	0.28389 (15)	0.0269 (5)
C65	0.49412 (16)	0.3236 (3)	0.19727 (15)	0.0260 (5)
C66	0.49349 (16)	0.4370 (3)	0.16411 (14)	0.0255 (5)
C71	0.4981 (2)	0.7334 (4)	0.18240 (18)	0.0395 (7)
H71A	0.5646	0.7466	0.1778	0.059*	0.50
H71B	0.4536	0.8484	0.2202	0.059*	0.50
H71C	0.4750	0.6851	0.1264	0.059*	0.50
H71D	0.4309	0.7735	0.1718	0.059*	0.50
H71E	0.5419	0.6717	0.1294	0.059*	0.50
H71F	0.5205	0.8350	0.2232	0.059*	0.50
C72	0.5133 (2)	0.8552 (4)	0.36225 (17)	0.0398 (7)
H72A	0.5351	0.8657	0.4158	0.060*	0.50
H72B	0.4487	0.9374	0.3732	0.060*	0.50
H72C	0.5609	0.8829	0.3349	0.060*	0.50
H72D	0.4947	0.9250	0.3335	0.060*	0.50
H72E	0.5811	0.8533	0.3760	0.060*	0.50
H72F	0.4689	0.9077	0.4143	0.060*	0.50
C73	0.5162 (2)	0.6131 (4)	0.42995 (16)	0.0403 (7)
H73A	0.5086	0.7403	0.4604	0.060*	0.50
H73B	0.5810	0.5528	0.4362	0.060*	0.50
H73C	0.4648	0.5848	0.4532	0.060*	0.50
H73D	0.5277	0.5117	0.4394	0.060*	0.50
H73E	0.4552	0.6992	0.4637	0.060*	0.50
H73F	0.5715	0.6671	0.4467	0.060*	0.50
C74	0.5007 (2)	0.2581 (4)	0.31921 (19)	0.0436 (8)
H74A	0.4635	0.3240	0.3755	0.065*	0.50
H74B	0.5686	0.2053	0.3232	0.065*	0.50
H74C	0.4701	0.1653	0.2817	0.065*	0.50
H74D	0.5380	0.1390	0.2781	0.065*	0.50
H74E	0.4328	0.2577	0.3304	0.065*	0.50
H74F	0.5314	0.2978	0.3719	0.065*	0.50
C75	0.4863 (2)	0.1365 (4)	0.13967 (18)	0.0408 (7)
H75A	0.4712	0.1227	0.0841	0.061*	0.50
H75B	0.4337	0.1135	0.1645	0.061*	0.50
H75C	0.5489	0.0531	0.1334	0.061*	0.50
H75D	0.4980	0.0702	0.1705	0.061*	0.50
H75E	0.5355	0.0794	0.0902	0.061*	0.50
H75F	0.4203	0.1398	0.1213	0.061*	0.50
C76	0.4853 (2)	0.3767 (4)	0.07133 (16)	0.0411 (7)
H76A	0.4884	0.2510	0.0416	0.062*	0.50
H76B	0.5397	0.3974	0.0474	0.062*	0.50
H76C	0.4225	0.4427	0.0649	0.062*	0.50
H76D	0.4787	0.4764	0.0610	0.062*	0.50
H76E	0.4274	0.3300	0.0552	0.062*	0.50
H76F	0.5446	0.2847	0.0377	0.062*	0.50
C1'	0.2557 (3)	0.8449 (5)	0.9618 (2)	0.0181 (6)	0.1848 (10)
C2'	0.2499 (3)	0.6717 (5)	0.9119 (2)	0.0182 (6)	0.1848 (10)
C3'	0.2452 (3)	0.6050 (4)	0.8249 (2)	0.0183 (6)	0.1848 (10)
C4'	0.2464 (5)	0.7105 (5)	0.7886 (2)	0.0183 (6)	0.1848 (10)
C5'	0.2522 (5)	0.8835 (5)	0.8377 (2)	0.0200 (6)	0.1848 (10)
C6'	0.2564 (5)	0.9497 (5)	0.9246 (2)	0.0192 (6)	0.1848 (10)
C7'	0.2609 (5)	0.9158 (7)	1.0525 (2)	0.0258 (2)	0.1848 (10)
N1'	0.2647 (5)	0.9716 (14)	1.1226 (2)	0.0258 (2)	0.1848 (10)
C8'	0.2392 (5)	0.4243 (5)	0.7743 (3)	0.0270 (2)	0.1848 (10)
N3'	0.2350 (6)	0.2835 (6)	0.7332 (7)	0.0270 (2)	0.1848 (10)
Cl2'	0.2484 (3)	0.5429 (4)	0.95753 (19)	0.0281 (2)	0.1848 (10)
Cl4'	0.2399 (3)	0.6242 (4)	0.68203 (13)	0.0292 (4)	0.1848 (10)
Cl5'	0.2531 (3)	1.0153 (4)	0.79363 (19)	0.0301 (2)	0.1848 (10)
Cl6'	0.2635 (3)	1.1613 (3)	0.98771 (17)	0.0295 (4)	0.1848 (10)
C11'	0.2445 (3)	0.6574 (5)	0.2926 (2)	0.0186 (6)	0.1848 (10)
C12'	0.2463 (3)	0.8327 (5)	0.3441 (2)	0.0207 (6)	0.1848 (10)
C13'	0.2525 (3)	0.8963 (4)	0.4303 (2)	0.0191 (6)	0.1848 (10)
C14'	0.2568 (5)	0.7863 (5)	0.4651 (2)	0.0195 (6)	0.1848 (10)
C15'	0.2553 (5)	0.6109 (5)	0.4142 (2)	0.0195 (6)	0.1848 (10)
C16'	0.2493 (5)	0.5484 (5)	0.3278 (2)	0.0201 (6)	0.1848 (10)
C17'	0.2377 (5)	0.5898 (7)	0.2020 (2)	0.0261 (2)	0.1848 (10)
N11'	0.2328 (5)	0.5382 (14)	0.1329 (2)	0.0261 (2)	0.1848 (10)
C18'	0.2539 (5)	1.0791 (5)	0.4830 (3)	0.0273 (2)	0.1848 (10)
N13'	0.2554 (6)	1.2225 (6)	0.5220 (7)	0.0273 (2)	0.1848 (10)
Cl22	0.2410 (3)	0.9676 (4)	0.30103 (19)	0.0280 (2)	0.1848 (10)
Cl24	0.2652 (2)	0.8685 (4)	0.57146 (13)	0.0277 (4)	0.1848 (10)
Cl25	0.2589 (3)	0.4745 (3)	0.45677 (17)	0.0295 (2)	0.1848 (10)
Cl26	0.2471 (3)	0.3343 (3)	0.26303 (16)	0.0282 (4)	0.1848 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0201 (11)	0.0209 (15)	0.0110 (10)	−0.0022 (11)	0.0027 (8)	0.0066 (11)
C2	0.0217 (12)	0.0207 (15)	0.0163 (11)	−0.0031 (11)	0.0033 (9)	0.0089 (11)
C3	0.0209 (12)	0.0203 (15)	0.0145 (11)	−0.0059 (10)	0.0031 (9)	0.0064 (11)
C4	0.0185 (11)	0.0178 (14)	0.0104 (10)	−0.0009 (10)	0.0036 (8)	0.0026 (10)
C5	0.0195 (11)	0.0188 (15)	0.0150 (11)	−0.0016 (10)	0.0038 (8)	0.0085 (11)
C6	0.0210 (12)	0.0123 (14)	0.0142 (11)	−0.0011 (10)	0.0022 (8)	0.0019 (10)
C7	0.0393 (8)	0.0262 (10)	0.0168 (8)	−0.0078 (7)	−0.0020 (7)	0.0066 (7)
N1	0.0393 (8)	0.0262 (10)	0.0168 (8)	−0.0078 (7)	−0.0020 (7)	0.0066 (7)
C8	0.0434 (9)	0.0205 (13)	0.0182 (10)	−0.0059 (10)	0.0034 (8)	0.0052 (10)
N3	0.0434 (9)	0.0205 (13)	0.0182 (10)	−0.0059 (10)	0.0034 (8)	0.0052 (10)
Cl2	0.0431 (4)	0.0287 (5)	0.0243 (4)	−0.0097 (4)	−0.0004 (3)	0.0172 (3)
Cl4	0.0352 (4)	0.0278 (4)	0.0106 (3)	−0.0074 (3)	0.0004 (2)	0.0066 (3)
Cl5	0.0419 (4)	0.0218 (4)	0.0219 (3)	−0.0067 (4)	0.0019 (3)	0.0120 (3)
Cl6	0.0376 (4)	0.0167 (4)	0.0197 (4)	−0.0078 (3)	−0.0001 (3)	0.0029 (3)
C11	0.0198 (12)	0.0206 (15)	0.0124 (11)	−0.0040 (11)	0.0035 (8)	0.0040 (11)
C12	0.0215 (12)	0.0154 (14)	0.0170 (12)	−0.0022 (10)	0.0027 (9)	0.0052 (11)
C13	0.0215 (12)	0.0181 (15)	0.0177 (12)	−0.0048 (11)	0.0036 (9)	0.0063 (11)
C14	0.0179 (11)	0.0200 (15)	0.0118 (11)	−0.0033 (10)	0.0029 (8)	0.0035 (10)
C15	0.0238 (12)	0.0190 (15)	0.0173 (11)	−0.0013 (10)	0.0023 (9)	0.0090 (11)
C16	0.0219 (12)	0.0128 (14)	0.0142 (11)	−0.0018 (10)	0.0022 (9)	0.0011 (10)
C17	0.0367 (8)	0.0262 (10)	0.0168 (8)	−0.0089 (8)	−0.0010 (7)	0.0074 (6)
N11	0.0367 (8)	0.0262 (10)	0.0168 (8)	−0.0089 (8)	−0.0010 (7)	0.0074 (6)
C18	0.0395 (9)	0.0233 (12)	0.0175 (9)	−0.0114 (9)	−0.0017 (7)	0.0050 (10)
N13	0.0395 (9)	0.0233 (12)	0.0175 (9)	−0.0114 (9)	−0.0017 (7)	0.0050 (10)
Cl12	0.0423 (4)	0.0278 (5)	0.0242 (4)	−0.0093 (4)	−0.0008 (3)	0.0169 (3)
Cl14	0.0364 (4)	0.0274 (4)	0.0097 (3)	−0.0077 (3)	0.0008 (3)	0.0053 (3)
Cl15	0.0416 (4)	0.0229 (4)	0.0220 (3)	−0.0082 (3)	0.0014 (3)	0.0128 (3)
Cl16	0.0390 (4)	0.0159 (4)	0.0198 (4)	−0.0088 (3)	−0.0009 (3)	0.0023 (3)
C21	0.0237 (12)	0.0254 (14)	0.0245 (12)	−0.0064 (10)	0.0005 (9)	0.0061 (11)
C22	0.0235 (12)	0.0313 (15)	0.0265 (13)	−0.0008 (10)	0.0022 (9)	0.0133 (11)
C23	0.0195 (11)	0.0359 (15)	0.0181 (12)	−0.0033 (10)	0.0022 (9)	0.0068 (11)
C31	0.0421 (16)	0.0433 (18)	0.0419 (16)	−0.0045 (14)	0.0027 (12)	0.0260 (15)
C32	0.0435 (17)	0.0324 (17)	0.0348 (16)	−0.0099 (13)	−0.0021 (12)	0.0031 (13)
C33	0.0435 (16)	0.052 (2)	0.0216 (13)	−0.0154 (14)	−0.0036 (11)	0.0116 (14)
C41	0.0241 (12)	0.0273 (14)	0.0237 (12)	−0.0064 (10)	0.0032 (9)	0.0073 (11)
C42	0.0246 (12)	0.0329 (15)	0.0251 (12)	−0.0033 (10)	0.0044 (9)	0.0152 (11)
C43	0.0192 (11)	0.0356 (14)	0.0182 (11)	−0.0055 (10)	0.0030 (9)	0.0094 (11)
C51	0.0423 (16)	0.0458 (19)	0.0430 (17)	−0.0037 (14)	0.0057 (12)	0.0290 (16)
C52	0.0454 (17)	0.0343 (17)	0.0358 (16)	−0.0131 (13)	0.0010 (12)	0.0051 (14)
C53	0.0419 (16)	0.056 (2)	0.0216 (13)	−0.0140 (14)	−0.0031 (11)	0.0137 (14)
C61	0.0224 (11)	0.0278 (13)	0.0247 (12)	−0.0038 (9)	0.0019 (9)	0.0123 (11)
C62	0.0206 (12)	0.0258 (14)	0.0255 (12)	−0.0038 (10)	0.0013 (9)	0.0094 (11)
C63	0.0182 (11)	0.0336 (14)	0.0187 (11)	−0.0041 (9)	0.0015 (8)	0.0101 (10)
C64	0.0228 (12)	0.0308 (14)	0.0279 (13)	−0.0045 (10)	0.0022 (9)	0.0159 (11)
C65	0.0211 (11)	0.0230 (13)	0.0271 (12)	−0.0028 (10)	0.0014 (9)	0.0080 (11)
C66	0.0179 (11)	0.0335 (14)	0.0196 (12)	−0.0034 (9)	0.0011 (9)	0.0100 (10)
C71	0.0424 (16)	0.0408 (18)	0.0434 (16)	−0.0024 (13)	0.0020 (12)	0.0303 (15)
C72	0.0419 (16)	0.0311 (16)	0.0338 (15)	−0.0119 (13)	−0.0002 (12)	0.0049 (13)
C73	0.0422 (16)	0.057 (2)	0.0220 (13)	−0.0159 (14)	−0.0008 (11)	0.0177 (14)
C74	0.0472 (17)	0.0428 (19)	0.0474 (17)	−0.0022 (14)	0.0054 (13)	0.0311 (16)
C75	0.0425 (17)	0.0301 (16)	0.0383 (16)	−0.0116 (13)	−0.0014 (12)	0.0067 (13)
C76	0.0395 (16)	0.055 (2)	0.0218 (13)	−0.0112 (14)	−0.0011 (11)	0.0141 (14)
C1'	0.0185 (11)	0.0178 (14)	0.0104 (10)	−0.0009 (10)	0.0036 (8)	0.0026 (10)
C2'	0.0195 (11)	0.0188 (15)	0.0150 (11)	−0.0016 (10)	0.0038 (8)	0.0085 (11)
C3'	0.0210 (12)	0.0123 (14)	0.0142 (11)	−0.0011 (10)	0.0022 (8)	0.0019 (10)
C4'	0.0201 (11)	0.0209 (15)	0.0110 (10)	−0.0022 (11)	0.0027 (8)	0.0066 (11)
C5'	0.0217 (12)	0.0207 (15)	0.0163 (11)	−0.0031 (11)	0.0033 (9)	0.0089 (11)
C6'	0.0209 (12)	0.0203 (15)	0.0145 (11)	−0.0059 (10)	0.0031 (9)	0.0064 (11)
C7'	0.0352 (4)	0.0278 (4)	0.0106 (3)	−0.0074 (3)	0.0004 (2)	0.0066 (3)
N1'	0.0352 (4)	0.0278 (4)	0.0106 (3)	−0.0074 (3)	0.0004 (2)	0.0066 (3)
C8'	0.0376 (4)	0.0167 (4)	0.0197 (4)	−0.0078 (3)	−0.0001 (3)	0.0029 (3)
N3'	0.0376 (4)	0.0167 (4)	0.0197 (4)	−0.0078 (3)	−0.0001 (3)	0.0029 (3)
Cl2'	0.0419 (4)	0.0218 (4)	0.0219 (3)	−0.0067 (4)	0.0019 (3)	0.0120 (3)
Cl4'	0.0393 (8)	0.0262 (10)	0.0168 (8)	−0.0078 (7)	−0.0020 (7)	0.0066 (7)
Cl5'	0.0431 (4)	0.0287 (5)	0.0243 (4)	−0.0097 (4)	−0.0004 (3)	0.0172 (3)
Cl6'	0.0434 (9)	0.0205 (13)	0.0182 (10)	−0.0059 (10)	0.0034 (8)	0.0052 (10)
C11'	0.0179 (11)	0.0200 (15)	0.0118 (11)	−0.0033 (10)	0.0029 (8)	0.0035 (10)
C12'	0.0238 (12)	0.0190 (15)	0.0173 (11)	−0.0013 (10)	0.0023 (9)	0.0090 (11)
C13'	0.0219 (12)	0.0128 (14)	0.0142 (11)	−0.0018 (10)	0.0022 (9)	0.0011 (10)
C14'	0.0198 (12)	0.0206 (15)	0.0124 (11)	−0.0040 (11)	0.0035 (8)	0.0040 (11)
C15'	0.0215 (12)	0.0154 (14)	0.0170 (12)	−0.0022 (10)	0.0027 (9)	0.0052 (11)
C16'	0.0215 (12)	0.0181 (15)	0.0177 (12)	−0.0048 (11)	0.0036 (9)	0.0063 (11)
C17'	0.0364 (4)	0.0274 (4)	0.0097 (3)	−0.0077 (3)	0.0008 (3)	0.0053 (3)
N11'	0.0364 (4)	0.0274 (4)	0.0097 (3)	−0.0077 (3)	0.0008 (3)	0.0053 (3)
C18'	0.0390 (4)	0.0159 (4)	0.0198 (4)	−0.0088 (3)	−0.0009 (3)	0.0023 (3)
N13'	0.0390 (4)	0.0159 (4)	0.0198 (4)	−0.0088 (3)	−0.0009 (3)	0.0023 (3)
Cl22	0.0416 (4)	0.0229 (4)	0.0220 (3)	−0.0082 (3)	0.0014 (3)	0.0128 (3)
Cl24	0.0367 (8)	0.0262 (10)	0.0168 (8)	−0.0089 (8)	−0.0010 (7)	0.0074 (6)
Cl25	0.0423 (4)	0.0278 (5)	0.0242 (4)	−0.0093 (4)	−0.0008 (3)	0.0169 (3)
Cl26	0.0395 (9)	0.0233 (12)	0.0175 (9)	−0.0114 (9)	−0.0017 (7)	0.0050 (10)

Geometric parameters (Å, º)

C1—C6	1.394 (4)	C53—H53F	0.9800
C1—C2	1.397 (4)	C61—C66	1.404 (3)
C1—C7	1.462 (4)	C61—C62	1.410 (3)
C2—C3	1.402 (3)	C61—C71	1.519 (3)
C2—Cl2	1.714 (3)	C62—C63	1.406 (3)
C3—C4	1.387 (4)	C62—C72	1.524 (3)
C3—C8	1.455 (4)	C63—C64	1.398 (3)
C4—C5	1.394 (4)	C63—C73	1.513 (3)
C4—Cl4	1.716 (2)	C64—C65	1.408 (3)
C5—C6	1.399 (3)	C64—C74	1.521 (4)
C5—Cl5	1.713 (3)	C65—C66	1.403 (3)
C6—Cl6	1.713 (3)	C65—C75	1.526 (3)
C7—N1	1.128 (4)	C66—C76	1.513 (3)
C8—N3	1.135 (4)	C71—H71A	0.9800
C11—C16	1.387 (4)	C71—H71B	0.9800
C11—C12	1.400 (4)	C71—H71C	0.9800
C11—C17	1.465 (4)	C71—H71D	0.9800
C12—C13	1.393 (3)	C71—H71E	0.9800
C12—Cl12	1.712 (3)	C71—H71F	0.9800
C13—C14	1.390 (4)	C72—H72A	0.9800
C13—C18	1.456 (4)	C72—H72B	0.9800
C14—C15	1.399 (4)	C72—H72C	0.9800
C14—Cl14	1.719 (3)	C72—H72D	0.9800
C15—C16	1.399 (3)	C72—H72E	0.9800
C15—Cl15	1.719 (3)	C72—H72F	0.9800
C16—Cl16	1.714 (3)	C73—H73A	0.9800
C17—N11	1.118 (4)	C73—H73B	0.9800
C18—N13	1.139 (4)	C73—H73C	0.9800
C21—C23	1.397 (4)	C73—H73D	0.9800
C21—C22	1.414 (3)	C73—H73E	0.9800
C21—C32	1.518 (4)	C73—H73F	0.9800
C22—C23^i	1.415 (4)	C74—H74A	0.9800
C22—C31	1.510 (3)	C74—H74B	0.9800
C23—C22^i	1.415 (4)	C74—H74C	0.9800
C23—C33	1.522 (3)	C74—H74D	0.9800
C31—H31A	0.9800	C74—H74E	0.9800
C31—H31B	0.9800	C74—H74F	0.9800
C31—H31C	0.9800	C75—H75A	0.9800
C31—H31D	0.9800	C75—H75B	0.9800
C31—H31E	0.9800	C75—H75C	0.9800
C31—H31F	0.9800	C75—H75D	0.9800
C32—H32A	0.9800	C75—H75E	0.9800
C32—H32B	0.9800	C75—H75F	0.9800
C32—H32C	0.9800	C76—H76A	0.9800
C32—H32D	0.9800	C76—H76B	0.9800
C32—H32E	0.9800	C76—H76C	0.9800
C32—H32F	0.9800	C76—H76D	0.9800
C33—H33A	0.9800	C76—H76E	0.9800
C33—H33B	0.9800	C76—H76F	0.9800
C33—H33C	0.9800	C1'—C6'	1.393 (4)
C33—H33D	0.9800	C1'—C2'	1.397 (4)
C33—H33E	0.9800	C1'—C7'	1.462 (4)
C33—H33F	0.9800	C2'—C3'	1.401 (3)
C41—C43	1.401 (4)	C2'—Cl2'	1.714 (3)
C41—C42	1.412 (3)	C3'—C4'	1.387 (4)
C41—C52	1.521 (4)	C3'—C8'	1.455 (4)
C42—C43^ii	1.405 (4)	C4'—C5'	1.394 (4)
C42—C51	1.512 (3)	C4'—Cl4'	1.716 (3)
C43—C42^ii	1.405 (4)	C5'—C6'	1.399 (3)
C43—C53	1.519 (3)	C5'—Cl5'	1.713 (3)
C51—H51A	0.9800	C6'—Cl6'	1.712 (3)
C51—H51B	0.9800	C7'—N1'	1.128 (4)
C51—H51C	0.9800	C8'—N3'	1.135 (4)
C51—H51D	0.9800	C11'—C16'	1.387 (4)
C51—H51E	0.9800	C11'—C12'	1.400 (4)
C51—H51F	0.9800	C11'—C17'	1.465 (4)
C52—H52A	0.9801	C12'—C13'	1.393 (4)
C52—H52B	0.9801	C12'—Cl22	1.711 (3)
C52—H52C	0.9801	C13'—C14'	1.391 (4)
C52—H52D	0.9801	C13'—C18'	1.457 (4)
C52—H52E	0.9801	C14'—C15'	1.398 (4)
C52—H52F	0.9801	C14'—Cl24	1.719 (3)
C53—H53A	0.9800	C15'—C16'	1.400 (4)
C53—H53B	0.9800	C15'—Cl25	1.719 (3)
C53—H53C	0.9800	C16'—Cl26	1.714 (3)
C53—H53D	0.9800	C17'—N11'	1.118 (4)
C53—H53E	0.9800	C18'—N13'	1.139 (4)
C6—C1—C2	119.7 (2)	C66—C61—C62	120.0 (2)
C6—C1—C7	120.1 (2)	C66—C61—C71	119.8 (2)
C2—C1—C7	120.2 (3)	C62—C61—C71	120.2 (2)
C1—C2—C3	119.7 (2)	C63—C62—C61	120.1 (2)
C1—C2—Cl2	119.8 (2)	C63—C62—C72	120.3 (2)
C3—C2—Cl2	120.5 (2)	C61—C62—C72	119.6 (2)
C4—C3—C2	120.0 (2)	C64—C63—C62	119.9 (2)
C4—C3—C8	121.3 (2)	C64—C63—C73	119.4 (2)
C2—C3—C8	118.6 (3)	C62—C63—C73	120.7 (2)
C3—C4—C5	120.8 (2)	C63—C64—C65	120.0 (2)
C3—C4—Cl4	118.7 (2)	C63—C64—C74	120.1 (2)
C5—C4—Cl4	120.5 (2)	C65—C64—C74	120.0 (2)
C4—C5—C6	118.9 (2)	C66—C65—C64	120.4 (2)
C4—C5—Cl5	121.03 (19)	C66—C65—C75	120.1 (2)
C6—C5—Cl5	120.0 (2)	C64—C65—C75	119.5 (2)
C1—C6—C5	120.9 (2)	C65—C66—C61	119.6 (2)
C1—C6—Cl6	118.3 (2)	C65—C66—C76	121.0 (2)
C5—C6—Cl6	120.9 (2)	C61—C66—C76	119.4 (2)
N1—C7—C1	177.8 (4)	C61—C71—H71A	109.5
N3—C8—C3	178.6 (4)	C61—C71—H71B	109.5
C16—C11—C12	119.6 (2)	H71A—C71—H71B	109.5
C16—C11—C17	120.2 (2)	C61—C71—H71C	109.5
C12—C11—C17	120.1 (3)	H71A—C71—H71C	109.5
C13—C12—C11	119.8 (2)	H71B—C71—H71C	109.5
C13—C12—Cl12	120.4 (2)	C61—C71—H71D	109.5
C11—C12—Cl12	119.8 (2)	H71A—C71—H71D	141.1
C14—C13—C12	120.2 (2)	H71B—C71—H71D	56.3
C14—C13—C18	120.8 (2)	H71C—C71—H71D	56.3
C12—C13—C18	119.1 (3)	C61—C71—H71E	109.5
C13—C14—C15	120.6 (2)	H71A—C71—H71E	56.3
C13—C14—Cl14	119.1 (2)	H71B—C71—H71E	141.1
C15—C14—Cl14	120.4 (2)	H71C—C71—H71E	56.3
C16—C15—C14	118.7 (2)	H71D—C71—H71E	109.5
C16—C15—Cl15	120.4 (2)	C61—C71—H71F	109.5
C14—C15—Cl15	120.9 (2)	H71A—C71—H71F	56.3
C11—C16—C15	121.1 (2)	H71B—C71—H71F	56.3
C11—C16—Cl16	118.5 (2)	H71C—C71—H71F	141.1
C15—C16—Cl16	120.4 (2)	H71D—C71—H71F	109.5
N11—C17—C11	178.6 (3)	H71E—C71—H71F	109.5
N13—C18—C13	178.8 (3)	C62—C72—H72A	109.5
C23—C21—C22	120.3 (2)	C62—C72—H72B	109.5
C23—C21—C32	120.1 (2)	H72A—C72—H72B	109.5
C22—C21—C32	119.7 (3)	C62—C72—H72C	109.5
C21—C22—C23^i	119.6 (2)	H72A—C72—H72C	109.5
C21—C22—C31	119.9 (2)	H72B—C72—H72C	109.5
C23^i—C22—C31	120.5 (2)	C62—C72—H72D	109.5
C21—C23—C22^i	120.1 (2)	H72A—C72—H72D	141.1
C21—C23—C33	120.6 (2)	H72B—C72—H72D	56.3
C22^i—C23—C33	119.3 (2)	H72C—C72—H72D	56.3
C22—C31—H31A	109.5	C62—C72—H72E	109.5
C22—C31—H31B	109.5	H72A—C72—H72E	56.3
H31A—C31—H31B	109.5	H72B—C72—H72E	141.1
C22—C31—H31C	109.5	H72C—C72—H72E	56.3
H31A—C31—H31C	109.5	H72D—C72—H72E	109.5
H31B—C31—H31C	109.5	C62—C72—H72F	109.5
C22—C31—H31D	109.5	H72A—C72—H72F	56.3
H31A—C31—H31D	141.1	H72B—C72—H72F	56.3
H31B—C31—H31D	56.3	H72C—C72—H72F	141.1
H31C—C31—H31D	56.3	H72D—C72—H72F	109.5
C22—C31—H31E	109.5	H72E—C72—H72F	109.5
H31A—C31—H31E	56.3	C63—C73—H73A	109.5
H31B—C31—H31E	141.1	C63—C73—H73B	109.5
H31C—C31—H31E	56.3	H73A—C73—H73B	109.5
H31D—C31—H31E	109.5	C63—C73—H73C	109.5
C22—C31—H31F	109.5	H73A—C73—H73C	109.5
H31A—C31—H31F	56.3	H73B—C73—H73C	109.5
H31B—C31—H31F	56.3	C63—C73—H73D	109.5
H31C—C31—H31F	141.1	H73A—C73—H73D	141.1
H31D—C31—H31F	109.5	H73B—C73—H73D	56.3
H31E—C31—H31F	109.5	H73C—C73—H73D	56.3
C21—C32—H32A	109.5	C63—C73—H73E	109.5
C21—C32—H32B	109.5	H73A—C73—H73E	56.3
H32A—C32—H32B	109.5	H73B—C73—H73E	141.1
C21—C32—H32C	109.5	H73C—C73—H73E	56.3
H32A—C32—H32C	109.5	H73D—C73—H73E	109.5
H32B—C32—H32C	109.5	C63—C73—H73F	109.5
C21—C32—H32D	109.5	H73A—C73—H73F	56.3
H32A—C32—H32D	141.1	H73B—C73—H73F	56.3
H32B—C32—H32D	56.3	H73C—C73—H73F	141.1
H32C—C32—H32D	56.3	H73D—C73—H73F	109.5
C21—C32—H32E	109.5	H73E—C73—H73F	109.5
H32A—C32—H32E	56.3	C64—C74—H74A	109.5
H32B—C32—H32E	141.1	C64—C74—H74B	109.5
H32C—C32—H32E	56.3	H74A—C74—H74B	109.5
H32D—C32—H32E	109.5	C64—C74—H74C	109.5
C21—C32—H32F	109.5	H74A—C74—H74C	109.5
H32A—C32—H32F	56.3	H74B—C74—H74C	109.5
H32B—C32—H32F	56.3	C64—C74—H74D	109.5
H32C—C32—H32F	141.1	H74A—C74—H74D	141.1
H32D—C32—H32F	109.5	H74B—C74—H74D	56.3
H32E—C32—H32F	109.5	H74C—C74—H74D	56.3
C23—C33—H33A	109.5	C64—C74—H74E	109.5
C23—C33—H33B	109.5	H74A—C74—H74E	56.3
H33A—C33—H33B	109.5	H74B—C74—H74E	141.1
C23—C33—H33C	109.5	H74C—C74—H74E	56.3
H33A—C33—H33C	109.5	H74D—C74—H74E	109.5
H33B—C33—H33C	109.5	C64—C74—H74F	109.5
C23—C33—H33D	109.5	H74A—C74—H74F	56.3
H33A—C33—H33D	141.1	H74B—C74—H74F	56.3
H33B—C33—H33D	56.3	H74C—C74—H74F	141.1
H33C—C33—H33D	56.3	H74D—C74—H74F	109.5
C23—C33—H33E	109.5	H74E—C74—H74F	109.5
H33A—C33—H33E	56.3	C65—C75—H75A	109.5
H33B—C33—H33E	141.1	C65—C75—H75B	109.5
H33C—C33—H33E	56.3	H75A—C75—H75B	109.5
H33D—C33—H33E	109.5	C65—C75—H75C	109.5
C23—C33—H33F	109.5	H75A—C75—H75C	109.5
H33A—C33—H33F	56.3	H75B—C75—H75C	109.5
H33B—C33—H33F	56.3	C65—C75—H75D	109.5
H33C—C33—H33F	141.1	H75A—C75—H75D	141.1
H33D—C33—H33F	109.5	H75B—C75—H75D	56.3
H33E—C33—H33F	109.5	H75C—C75—H75D	56.3
C43—C41—C42	120.0 (2)	C65—C75—H75E	109.5
C43—C41—C52	120.1 (2)	H75A—C75—H75E	56.3
C42—C41—C52	119.8 (3)	H75B—C75—H75E	141.1
C43^ii—C42—C41	120.0 (2)	H75C—C75—H75E	56.3
C43^ii—C42—C51	120.0 (2)	H75D—C75—H75E	109.5
C41—C42—C51	120.0 (2)	C65—C75—H75F	109.5
C41—C43—C42^ii	120.0 (2)	H75A—C75—H75F	56.3
C41—C43—C53	120.5 (2)	H75B—C75—H75F	56.3
C42^ii—C43—C53	119.5 (2)	H75C—C75—H75F	141.1
C42—C51—H51A	109.5	H75D—C75—H75F	109.5
C42—C51—H51B	109.5	H75E—C75—H75F	109.5
H51A—C51—H51B	109.5	C66—C76—H76A	109.5
C42—C51—H51C	109.5	C66—C76—H76B	109.5
H51A—C51—H51C	109.5	H76A—C76—H76B	109.5
H51B—C51—H51C	109.5	C66—C76—H76C	109.5
C42—C51—H51D	109.5	H76A—C76—H76C	109.5
H51A—C51—H51D	141.1	H76B—C76—H76C	109.5
H51B—C51—H51D	56.3	C66—C76—H76D	109.5
H51C—C51—H51D	56.3	H76A—C76—H76D	141.1
C42—C51—H51E	109.5	H76B—C76—H76D	56.3
H51A—C51—H51E	56.3	H76C—C76—H76D	56.3
H51B—C51—H51E	141.1	C66—C76—H76E	109.5
H51C—C51—H51E	56.3	H76A—C76—H76E	56.3
H51D—C51—H51E	109.5	H76B—C76—H76E	141.1
C42—C51—H51F	109.5	H76C—C76—H76E	56.3
H51A—C51—H51F	56.3	H76D—C76—H76E	109.5
H51B—C51—H51F	56.3	C66—C76—H76F	109.5
H51C—C51—H51F	141.1	H76A—C76—H76F	56.3
H51D—C51—H51F	109.5	H76B—C76—H76F	56.3
H51E—C51—H51F	109.5	H76C—C76—H76F	141.1
C41—C52—H52A	109.5	H76D—C76—H76F	109.5
C41—C52—H52B	109.5	H76E—C76—H76F	109.5
H52A—C52—H52B	109.5	C6'—C1'—C2'	119.7 (2)
C41—C52—H52C	109.5	C6'—C1'—C7'	120.2 (3)
H52A—C52—H52C	109.5	C2'—C1'—C7'	120.2 (3)
H52B—C52—H52C	109.5	C1'—C2'—C3'	119.7 (2)
C41—C52—H52D	109.5	C1'—C2'—Cl2'	119.8 (2)
H52A—C52—H52D	141.0	C3'—C2'—Cl2'	120.5 (2)
H52B—C52—H52D	56.2	C4'—C3'—C2'	120.1 (3)
H52C—C52—H52D	56.2	C4'—C3'—C8'	121.3 (3)
C41—C52—H52E	109.5	C2'—C3'—C8'	118.6 (3)
H52A—C52—H52E	56.2	C3'—C4'—C5'	120.8 (2)
H52B—C52—H52E	141.0	C3'—C4'—Cl4'	118.6 (2)
H52C—C52—H52E	56.2	C5'—C4'—Cl4'	120.6 (2)
H52D—C52—H52E	109.5	C4'—C5'—C6'	118.9 (2)
C41—C52—H52F	109.5	C4'—C5'—Cl5'	121.2 (2)
H52A—C52—H52F	56.2	C6'—C5'—Cl5'	119.9 (2)
H52B—C52—H52F	56.2	C1'—C6'—C5'	120.9 (2)
H52C—C52—H52F	141.0	C1'—C6'—Cl6'	118.4 (2)
H52D—C52—H52F	109.5	C5'—C6'—Cl6'	120.7 (2)
H52E—C52—H52F	109.5	N1'—C7'—C1'	179.6 (8)
C43—C53—H53A	109.5	N3'—C8'—C3'	178.4 (7)
C43—C53—H53B	109.5	C16'—C11'—C12'	119.6 (2)
H53A—C53—H53B	109.5	C16'—C11'—C17'	120.3 (3)
C43—C53—H53C	109.5	C12'—C11'—C17'	120.1 (3)
H53A—C53—H53C	109.5	C13'—C12'—C11'	119.8 (3)
H53B—C53—H53C	109.5	C13'—C12'—Cl22	120.4 (2)
C43—C53—H53D	109.5	C11'—C12'—Cl22	119.8 (2)
H53A—C53—H53D	141.1	C14'—C13'—C12'	120.2 (3)
H53B—C53—H53D	56.3	C14'—C13'—C18'	120.7 (3)
H53C—C53—H53D	56.3	C12'—C13'—C18'	119.1 (3)
C43—C53—H53E	109.5	C13'—C14'—C15'	120.6 (2)
H53A—C53—H53E	56.3	C13'—C14'—Cl24	119.0 (2)
H53B—C53—H53E	141.1	C15'—C14'—Cl24	120.4 (2)
H53C—C53—H53E	56.3	C14'—C15'—C16'	118.7 (2)
H53D—C53—H53E	109.5	C14'—C15'—Cl25	121.0 (2)
C43—C53—H53F	109.5	C16'—C15'—Cl25	120.3 (2)
H53A—C53—H53F	56.3	C11'—C16'—C15'	121.1 (2)
H53B—C53—H53F	56.3	C11'—C16'—Cl26	118.6 (2)
H53C—C53—H53F	141.1	C15'—C16'—Cl26	120.3 (2)
H53D—C53—H53F	109.5	N11'—C17'—C11'	179.7 (6)
H53E—C53—H53F	109.5	N13'—C18'—C13'	177.8 (7)

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

(paraI) para tetrachlorodicyanobenzene/hexamethylbenzene, 1/1 polymorph I

Crystal data

C12H18·C8Cl4N2	Z = 1
Mr = 428.16	F(000) = 220
Triclinic, P1	Dx = 1.494 Mg m^−3
a = 7.513 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.615 (3) Å	Cell parameters from 24 reflections
c = 9.029 (3) Å	θ = 11–28°
α = 114.24 (3)°	µ = 0.63 mm^−1
β = 113.30 (2)°	T = 189 K
γ = 91.92 (3)°	Sword-shaped, yellow
V = 475.8 (3) Å^3	0.50 × 0.35 × 0.15 mm

Data collection

CAD-4 diffractometer	2324 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.074
Graphite monochromator	θmax = 30.0°, θmin = 2.7°
ω–two θ scans	h = −10→4
Absorption correction: empirical (using intensity measurements) DIFABS, Walker, N. and Stuart, D. (1983) Acta Cryst. A39, 158-166.	k = −12→12
Tmin = 0.75, Tmax = 0.91	l = −12→12
4293 measured reflections	3 standard reflections every 60 min min
2775 independent reflections	intensity decay: less than 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.074	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.212	w = 1/[σ^2(Fo^2) + (0.098P)^2 + 0.96P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
2775 reflections	Δρmax = 0.57 e Å^−3
122 parameters	Δρmin = −0.65 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.09 (2)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.0391 (4)	0.0988 (4)	−0.0765 (4)	0.0190 (5)
C2	0.0801 (4)	0.1798 (4)	0.1069 (4)	0.0195 (5)
C3	0.0403 (4)	0.0797 (4)	0.1829 (4)	0.0192 (5)
C11	0.0763 (5)	0.2024 (4)	−0.1565 (4)	0.0231 (6)
N11	0.1016 (5)	0.2841 (4)	−0.2219 (4)	0.0314 (6)
Cl12	0.17471 (14)	0.40092 (10)	0.23184 (11)	0.0321 (3)
Cl13	0.09077 (12)	0.17518 (10)	0.40714 (10)	0.0265 (3)
C21	0.4191 (4)	0.8209 (4)	−0.1203 (4)	0.0219 (6)
C22	0.4591 (4)	0.9372 (4)	−0.1829 (4)	0.0212 (6)
C23	0.5411 (4)	1.1143 (4)	−0.0630 (4)	0.0213 (6)
C31	0.3321 (6)	0.6276 (5)	−0.2496 (5)	0.0322 (7)
H31A	0.3731	0.5943	−0.3443	0.048*	0.50
H31B	0.1892	0.6045	−0.3021	0.048*	0.50
H31C	0.3787	0.5613	−0.1843	0.048*	0.50
H31D	0.2543	0.5791	−0.2095	0.048*	0.50
H31E	0.4381	0.5689	−0.2517	0.048*	0.50
H31F	0.2486	0.6121	−0.3695	0.048*	0.50
C32	0.4074 (6)	0.8658 (5)	−0.3836 (5)	0.0334 (8)
H32A	0.2984	0.7644	−0.4543	0.050*	0.50
H32B	0.5213	0.8340	−0.4016	0.050*	0.50
H32C	0.3701	0.9539	−0.4213	0.050*	0.50
H32D	0.4948	0.9372	−0.3971	0.050*	0.50
H32E	0.2719	0.8675	−0.4499	0.050*	0.50
H32F	0.4231	0.7477	−0.4302	0.050*	0.50
C33	0.5876 (5)	1.2381 (5)	−0.1296 (5)	0.0311 (7)
H33A	0.5984	1.3560	−0.0466	0.047*	0.50
H33B	0.4827	1.2080	−0.2478	0.047*	0.50
H33C	0.7113	1.2289	−0.1367	0.047*	0.50
H33D	0.5965	1.1726	−0.2408	0.047*	0.50
H33E	0.7123	1.3206	−0.0396	0.047*	0.50
H33F	0.4836	1.2997	−0.1507	0.047*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0176 (12)	0.0244 (13)	0.0205 (12)	0.0050 (10)	0.0108 (10)	0.0130 (11)
C2	0.0189 (13)	0.0193 (13)	0.0206 (13)	0.0019 (10)	0.0101 (10)	0.0084 (11)
C3	0.0198 (13)	0.0244 (13)	0.0180 (12)	0.0072 (10)	0.0118 (10)	0.0107 (11)
C11	0.0230 (14)	0.0259 (14)	0.0246 (14)	0.0046 (11)	0.0131 (12)	0.0130 (12)
N11	0.0374 (16)	0.0327 (15)	0.0326 (14)	0.0071 (12)	0.0185 (13)	0.0200 (13)
Cl12	0.0437 (5)	0.0221 (4)	0.0287 (4)	0.0000 (3)	0.0183 (4)	0.0087 (3)
Cl13	0.0319 (4)	0.0300 (4)	0.0183 (4)	0.0048 (3)	0.0133 (3)	0.0098 (3)
C21	0.0175 (13)	0.0227 (14)	0.0257 (14)	0.0019 (10)	0.0094 (11)	0.0119 (12)
C22	0.0179 (13)	0.0266 (14)	0.0225 (13)	0.0049 (10)	0.0096 (11)	0.0138 (11)
C23	0.0155 (12)	0.0257 (14)	0.0265 (14)	0.0030 (10)	0.0088 (11)	0.0163 (12)
C31	0.0342 (18)	0.0245 (15)	0.0329 (17)	0.0018 (13)	0.0153 (15)	0.0091 (13)
C32	0.0340 (18)	0.042 (2)	0.0251 (15)	0.0036 (15)	0.0134 (14)	0.0165 (15)
C33	0.0307 (17)	0.0347 (17)	0.0391 (18)	0.0041 (13)	0.0154 (14)	0.0274 (15)

Geometric parameters (Å, º)

C1—C3^i	1.384 (4)	C31—H31C	0.9600
C1—C2	1.399 (4)	C31—H31D	0.9600
C1—C11	1.439 (4)	C31—H31E	0.9600
C2—C3	1.391 (4)	C31—H31F	0.9600
C2—Cl12	1.708 (3)	C32—H32A	0.9600
C3—C1^i	1.384 (4)	C32—H32B	0.9600
C3—Cl13	1.710 (3)	C32—H32C	0.9600
C11—N11	1.141 (4)	C32—H32D	0.9600
C21—C23^ii	1.407 (4)	C32—H32E	0.9600
C21—C22	1.412 (4)	C32—H32F	0.9600
C21—C31	1.513 (5)	C33—H33A	0.9600
C22—C23	1.391 (4)	C33—H33B	0.9600
C22—C32	1.525 (4)	C33—H33C	0.9600
C23—C21^ii	1.407 (4)	C33—H33D	0.9600
C23—C33	1.513 (4)	C33—H33E	0.9600
C31—H31A	0.9600	C33—H33F	0.9600
C31—H31B	0.9600
C3^i—C1—C2	120.8 (3)	C22—C32—H32B	109.5
C3^i—C1—C11	119.5 (3)	H32A—C32—H32B	109.5
C2—C1—C11	119.7 (3)	C22—C32—H32C	109.5
C3—C2—C1	119.5 (3)	H32A—C32—H32C	109.5
C3—C2—Cl12	121.4 (2)	H32B—C32—H32C	109.5
C1—C2—Cl12	119.1 (2)	C22—C32—H32D	109.5
C1^i—C3—C2	119.7 (3)	H32A—C32—H32D	141.1
C1^i—C3—Cl13	119.8 (2)	H32B—C32—H32D	56.3
C2—C3—Cl13	120.5 (2)	H32C—C32—H32D	56.2
N11—C11—C1	178.6 (4)	C22—C32—H32E	109.5
C23^ii—C21—C22	119.7 (3)	H32A—C32—H32E	56.3
C23^ii—C21—C31	119.9 (3)	H32B—C32—H32E	141.1
C22—C21—C31	120.4 (3)	H32C—C32—H32E	56.3
C23—C22—C21	120.1 (3)	H32D—C32—H32E	109.5
C23—C22—C32	120.9 (3)	C22—C32—H32F	109.5
C21—C22—C32	118.9 (3)	H32A—C32—H32F	56.3
C22—C23—C21^ii	120.2 (3)	H32B—C32—H32F	56.3
C22—C23—C33	120.0 (3)	H32C—C32—H32F	141.1
C21^ii—C23—C33	119.8 (3)	H32D—C32—H32F	109.5
C21—C31—H31A	109.5	H32E—C32—H32F	109.5
C21—C31—H31B	109.5	C23—C33—H33A	109.5
H31A—C31—H31B	109.5	C23—C33—H33B	109.5
C21—C31—H31C	109.5	H33A—C33—H33B	109.5
H31A—C31—H31C	109.5	C23—C33—H33C	109.5
H31B—C31—H31C	109.5	H33A—C33—H33C	109.5
C21—C31—H31D	109.5	H33B—C33—H33C	109.5
H31A—C31—H31D	141.1	C23—C33—H33D	109.5
H31B—C31—H31D	56.3	H33A—C33—H33D	141.1
H31C—C31—H31D	56.3	H33B—C33—H33D	56.3
C21—C31—H31E	109.5	H33C—C33—H33D	56.3
H31A—C31—H31E	56.3	C23—C33—H33E	109.5
H31B—C31—H31E	141.1	H33A—C33—H33E	56.3
H31C—C31—H31E	56.3	H33B—C33—H33E	141.1
H31D—C31—H31E	109.5	H33C—C33—H33E	56.3
C21—C31—H31F	109.5	H33D—C33—H33E	109.5
H31A—C31—H31F	56.3	C23—C33—H33F	109.5
H31B—C31—H31F	56.3	H33A—C33—H33F	56.3
H31C—C31—H31F	141.1	H33B—C33—H33F	56.3
H31D—C31—H31F	109.5	H33C—C33—H33F	141.1
H31E—C31—H31F	109.5	H33D—C33—H33F	109.5
C22—C32—H32A	109.5	H33E—C33—H33F	109.5

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

(paraII) para tetrachlorodicyanobenzene/hexamethylbenzene, 1/1, polymorph II

Crystal data

C8Cl4N2·C12H18	Z = 1
Mr = 428.16	F(000) = 220
Triclinic, P1	Dx = 1.467 Mg m^−3
a = 7.5567 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8956 (11) Å	Cell parameters from 876 reflections
c = 8.9921 (11) Å	θ = 4.5–27.5°
α = 116.697 (3)°	µ = 0.62 mm^−1
β = 112.099 (3)°	T = 174 K
γ = 92.101 (3)°	Plate, yellow
V = 484.66 (11) Å^3	0.45 × 0.25 × 0.15 mm

Data collection

Siemens SMART arae-detector diffractometer	2198 independent reflections
Radiation source: fine-focus sealed tube	1890 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995	h = −9→9
Tmin = 0.80, Tmax = 0.91	k = −11→11
5128 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.067P)^2 + 0.121P] where P = (Fo^2 + 2Fc^2)/3
2198 reflections	(Δ/σ)max = 0.003
122 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	−0.0078 (2)	−0.1001 (2)	−0.1743 (2)	0.0292 (3)
C2	−0.0065 (2)	−0.1770 (2)	−0.0679 (2)	0.0305 (3)
C3	0.0013 (2)	−0.0766 (2)	0.1063 (2)	0.0302 (3)
C7	−0.0196 (3)	−0.2039 (2)	−0.3571 (2)	0.0337 (4)
N1	−0.0339 (2)	−0.2857 (2)	−0.5039 (2)	0.0421 (4)
Cl2	−0.01561 (7)	−0.39377 (5)	−0.15658 (6)	0.04022 (16)
Cl3	0.00284 (7)	−0.16577 (6)	0.24079 (6)	0.03724 (15)
C11	0.5086 (2)	0.1775 (2)	0.0652 (2)	0.0358 (4)
C12	0.4922 (2)	0.0703 (3)	−0.1139 (2)	0.0365 (4)
C13	0.4848 (2)	−0.1067 (2)	−0.1783 (2)	0.0363 (4)
C21	0.5203 (3)	0.3698 (3)	0.1377 (3)	0.0507 (5)
H21A	0.4921	0.3946	0.0365	0.076*	0.50
H21B	0.6529	0.4373	0.2363	0.076*	0.50
H21C	0.4233	0.4017	0.1870	0.076*	0.50
H21D	0.5535	0.4278	0.2701	0.076*	0.50
H21E	0.3927	0.3851	0.0702	0.076*	0.50
H21F	0.6222	0.4207	0.1195	0.076*	0.50
C22	0.4800 (3)	0.1460 (3)	−0.2385 (3)	0.0500 (5)
H22A	0.5532	0.2684	−0.1620	0.075*	0.50
H22B	0.3417	0.1371	−0.3115	0.075*	0.50
H22C	0.5374	0.0813	−0.3222	0.075*	0.50
H22D	0.4017	0.0561	−0.3685	0.075*	0.50
H22E	0.6132	0.1874	−0.2190	0.075*	0.50
H22F	0.4174	0.2432	−0.2082	0.075*	0.50
C23	0.4692 (3)	−0.2219 (3)	−0.3704 (3)	0.0511 (5)
H23A	0.4131	−0.3431	−0.4134	0.077*	0.50
H23B	0.6006	−0.2102	−0.3662	0.077*	0.50
H23C	0.3837	−0.1869	−0.4558	0.077*	0.50
H23D	0.5185	−0.1504	−0.4102	0.077*	0.50
H23E	0.3310	−0.2832	−0.4574	0.077*	0.50
H23F	0.5479	−0.3066	−0.3678	0.077*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0273 (7)	0.0315 (8)	0.0241 (7)	0.0064 (6)	0.0108 (6)	0.0107 (6)
C2	0.0305 (8)	0.0273 (7)	0.0281 (8)	0.0068 (6)	0.0126 (7)	0.0098 (6)
C3	0.0298 (8)	0.0319 (8)	0.0266 (8)	0.0078 (6)	0.0123 (6)	0.0128 (6)
C7	0.0344 (8)	0.0335 (8)	0.0269 (8)	0.0074 (7)	0.0132 (7)	0.0106 (7)
N1	0.0499 (9)	0.0387 (8)	0.0326 (8)	0.0102 (7)	0.0201 (7)	0.0123 (7)
Cl2	0.0516 (3)	0.0271 (2)	0.0387 (3)	0.01224 (18)	0.0220 (2)	0.01191 (18)
Cl3	0.0453 (3)	0.0379 (2)	0.0327 (2)	0.01195 (18)	0.01876 (19)	0.01946 (19)
C11	0.0269 (8)	0.0395 (9)	0.0338 (9)	0.0061 (7)	0.0104 (7)	0.0154 (8)
C12	0.0278 (8)	0.0479 (10)	0.0324 (9)	0.0069 (7)	0.0105 (7)	0.0213 (8)
C13	0.0266 (8)	0.0465 (10)	0.0249 (8)	0.0057 (7)	0.0075 (7)	0.0128 (7)
C21	0.0470 (11)	0.0436 (11)	0.0547 (12)	0.0088 (9)	0.0215 (10)	0.0201 (10)
C22	0.0475 (11)	0.0667 (14)	0.0477 (12)	0.0160 (10)	0.0211 (10)	0.0376 (11)
C23	0.0479 (11)	0.0615 (13)	0.0305 (9)	0.0134 (10)	0.0168 (9)	0.0130 (9)

Geometric parameters (Å, º)

C1—C3^i	1.398 (2)	C21—H21C	0.9800
C1—C2	1.402 (2)	C21—H21D	0.9800
C1—C7	1.443 (2)	C21—H21E	0.9800
C2—C3	1.387 (2)	C21—H21F	0.9800
C2—Cl2	1.7106 (16)	C22—H22A	0.9800
C3—C1^i	1.398 (2)	C22—H22B	0.9800
C3—Cl3	1.7163 (16)	C22—H22C	0.9800
C7—N1	1.144 (2)	C22—H22D	0.9800
C11—C13^ii	1.405 (3)	C22—H22E	0.9800
C11—C12	1.407 (3)	C22—H22F	0.9800
C11—C21	1.518 (3)	C23—H23A	0.9800
C12—C13	1.403 (3)	C23—H23B	0.9800
C12—C22	1.524 (3)	C23—H23C	0.9800
C13—C11^ii	1.405 (3)	C23—H23D	0.9800
C13—C23	1.515 (2)	C23—H23E	0.9800
C21—H21A	0.9800	C23—H23F	0.9800
C21—H21B	0.9800
C3^i—C1—C2	120.54 (14)	C12—C22—H22B	109.5
C3^i—C1—C7	119.38 (14)	H22A—C22—H22B	109.5
C2—C1—C7	120.07 (15)	C12—C22—H22C	109.5
C3—C2—C1	119.56 (15)	H22A—C22—H22C	109.5
C3—C2—Cl2	121.35 (13)	H22B—C22—H22C	109.5
C1—C2—Cl2	119.09 (12)	C12—C22—H22D	109.5
C2—C3—C1^i	119.90 (15)	H22A—C22—H22D	141.1
C2—C3—Cl3	121.01 (13)	H22B—C22—H22D	56.3
C1^i—C3—Cl3	119.09 (12)	H22C—C22—H22D	56.3
N1—C7—C1	178.19 (19)	C12—C22—H22E	109.5
C13^ii—C11—C12	119.97 (17)	H22A—C22—H22E	56.3
C13^ii—C11—C21	119.65 (16)	H22B—C22—H22E	141.1
C12—C11—C21	120.37 (17)	H22C—C22—H22E	56.3
C13—C12—C11	119.86 (16)	H22D—C22—H22E	109.5
C13—C12—C22	120.09 (17)	C12—C22—H22F	109.5
C11—C12—C22	120.05 (18)	H22A—C22—H22F	56.3
C12—C13—C11^ii	120.17 (16)	H22B—C22—H22F	56.3
C12—C13—C23	119.94 (17)	H22C—C22—H22F	141.1
C11^ii—C13—C23	119.89 (18)	H22D—C22—H22F	109.5
C11—C21—H21A	109.5	H22E—C22—H22F	109.5
C11—C21—H21B	109.5	C13—C23—H23A	109.5
H21A—C21—H21B	109.5	C13—C23—H23B	109.5
C11—C21—H21C	109.5	H23A—C23—H23B	109.5
H21A—C21—H21C	109.5	C13—C23—H23C	109.5
H21B—C21—H21C	109.5	H23A—C23—H23C	109.5
C11—C21—H21D	109.5	H23B—C23—H23C	109.5
H21A—C21—H21D	141.1	C13—C23—H23D	109.5
H21B—C21—H21D	56.3	H23A—C23—H23D	141.1
H21C—C21—H21D	56.3	H23B—C23—H23D	56.3
C11—C21—H21E	109.5	H23C—C23—H23D	56.3
H21A—C21—H21E	56.3	C13—C23—H23E	109.5
H21B—C21—H21E	141.1	H23A—C23—H23E	56.3
H21C—C21—H21E	56.3	H23B—C23—H23E	141.1
H21D—C21—H21E	109.5	H23C—C23—H23E	56.3
C11—C21—H21F	109.5	H23D—C23—H23E	109.5
H21A—C21—H21F	56.3	C13—C23—H23F	109.5
H21B—C21—H21F	56.3	H23A—C23—H23F	56.3
H21C—C21—H21F	141.1	H23B—C23—H23F	56.3
H21D—C21—H21F	109.5	H23C—C23—H23F	141.1
H21E—C21—H21F	109.5	H23D—C23—H23F	109.5
C12—C22—H22A	109.5	H23E—C23—H23F	109.5

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

(paraIII) para tetrachlorodicyanobenzene/hexamethylbenzene, 1/1. polymorph III

Crystal data

C8N2Cl4·C12H18	F(000) = 440
Mr = 428.16	Dx = 1.404 Mg m^−3
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
a = 9.754 (2) Å	Cell parameters from 799 reflections
b = 15.410 (3) Å	θ = 2.6–26.9°
c = 7.5550 (15) Å	µ = 0.59 mm^−1
β = 116.88 (3)°	T = 297 K
V = 1012.9 (4) Å^3	Plate, yellow
Z = 2	0.45 × 0.25 × 0.15 mm

Data collection

Siemens SMART area-detector diffractometer	1204 independent reflections
Radiation source: fine-focus sealed tube	876 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995	h = −12→12
Tmin = 0.81, Tmax = 0.91	k = −20→19
5342 measured reflections	l = −9→9

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.09P)^2 + 0.226P] where P = (Fo^2 + 2Fc^2)/3
1204 reflections	(Δ/σ)max = 0.001
62 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.20945 (6)	0.10230 (4)	0.94792 (9)	0.0800 (3)
C1	0.5000	0.08984 (19)	1.0000	0.0612 (7)
C2	0.3683 (2)	0.04517 (14)	0.9764 (3)	0.0605 (5)
N1	0.5000	0.2567 (2)	1.0000	0.0998 (11)
C7	0.5000	0.1828 (2)	1.0000	0.0729 (8)
C12	0.1296 (3)	0.4553 (2)	0.5252 (3)	0.1007 (10)
C11	0.0000	0.4112 (3)	0.5000	0.1025 (15)
C22	0.2708 (6)	0.4049 (5)	0.5545 (6)	0.244 (5)
H22A	0.3454	0.4438	0.5486	0.366*	0.50
H22B	0.2433	0.3620	0.4520	0.366*	0.50
H22C	0.3134	0.3768	0.6817	0.366*	0.50
H22D	0.2560	0.3446	0.5729	0.366*	0.50
H22E	0.3581	0.4264	0.6695	0.366*	0.50
H22F	0.2880	0.4115	0.4398	0.366*	0.50
C21	0.0000	0.3127 (4)	0.5000	0.215 (5)
H21A	−0.0922	0.2920	0.5016	0.323*	0.25
H21B	0.0878	0.2920	0.6155	0.323*	0.25
H21C	0.0044	0.2920	0.3829	0.323*	0.25
H21D	0.0922	0.2920	0.4984	0.323*	0.25
H21E	−0.0878	0.2920	0.3845	0.323*	0.25
H21F	−0.0044	0.2920	0.6171	0.323*	0.25

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0535 (4)	0.0899 (5)	0.0987 (5)	0.0129 (2)	0.0363 (3)	0.0035 (3)
C1	0.0507 (14)	0.0701 (18)	0.0608 (16)	0.000	0.0235 (12)	0.000
C2	0.0454 (9)	0.0745 (12)	0.0602 (11)	0.0052 (8)	0.0227 (8)	0.0008 (9)
N1	0.084 (2)	0.078 (2)	0.147 (3)	0.000	0.061 (2)	0.000
C7	0.0616 (17)	0.069 (2)	0.090 (2)	0.000	0.0359 (16)	0.000
C12	0.0805 (16)	0.159 (3)	0.0569 (13)	0.0436 (17)	0.0262 (12)	0.0148 (14)
C11	0.154 (5)	0.087 (3)	0.073 (2)	0.000	0.056 (3)	0.000
C22	0.185 (5)	0.444 (13)	0.113 (3)	0.209 (7)	0.076 (4)	0.077 (5)
C21	0.430 (17)	0.090 (3)	0.145 (5)	0.000	0.147 (8)	0.000

Geometric parameters (Å, º)

Cl1—C2	1.709 (2)	C22—H22B	0.9600
C1—C2^i	1.396 (2)	C22—H22C	0.9600
C1—C2	1.396 (2)	C22—H22D	0.9600
C1—C7	1.433 (5)	C22—H22E	0.9600
C2—C2^ii	1.392 (4)	C22—H22F	0.9600
N1—C7	1.139 (4)	C21—H21A	0.9600
C12—C11	1.370 (4)	C21—H21B	0.9600
C12—C12^iii	1.378 (8)	C21—H21C	0.9600
C12—C22	1.507 (5)	C21—H21D	0.9600
C11—C12^iv	1.370 (4)	C21—H21E	0.9600
C11—C21	1.518 (7)	C21—H21F	0.9600
C22—H22A	0.9600
C2^i—C1—C2	120.9 (3)	C12—C22—H22F	109.5
C2^i—C1—C7	119.55 (13)	H22A—C22—H22F	56.3
C2—C1—C7	119.55 (13)	H22B—C22—H22F	56.3
C2^ii—C2—C1	119.55 (13)	H22C—C22—H22F	141.1
C2^ii—C2—Cl1	121.01 (8)	H22D—C22—H22F	109.5
C1—C2—Cl1	119.45 (17)	H22E—C22—H22F	109.5
N1—C7—C1	180.000 (1)	C11—C21—H21A	109.5
C11—C12—C12^iii	119.7 (2)	C11—C21—H21B	109.5
C11—C12—C22	119.3 (4)	H21A—C21—H21B	109.5
C12^iii—C12—C22	121.0 (3)	C11—C21—H21C	109.5
C12—C11—C12^iv	120.6 (4)	H21A—C21—H21C	109.5
C12—C11—C21	119.7 (2)	H21B—C21—H21C	109.5
C12^iv—C11—C21	119.7 (2)	C11—C21—H21D	109.5
C12—C22—H22A	109.5	H21A—C21—H21D	141.1
C12—C22—H22B	109.5	H21B—C21—H21D	56.3
H22A—C22—H22B	109.5	H21C—C21—H21D	56.3
C12—C22—H22C	109.5	C11—C21—H21E	109.5
H22A—C22—H22C	109.5	H21A—C21—H21E	56.3
H22B—C22—H22C	109.5	H21B—C21—H21E	141.1
C12—C22—H22D	109.5	H21C—C21—H21E	56.3
H22A—C22—H22D	141.1	H21D—C21—H21E	109.5
H22B—C22—H22D	56.3	C11—C21—H21F	109.5
H22C—C22—H22D	56.3	H21A—C21—H21F	56.3
C12—C22—H22E	109.5	H21B—C21—H21F	56.3
H22A—C22—H22E	56.3	H21C—C21—H21F	141.1
H22B—C22—H22E	141.1	H21D—C21—H21F	109.5
H22C—C22—H22E	56.3	H21E—C21—H21F	109.5
H22D—C22—H22E	109.5

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

(paraIV) para tetrachlorodicyanobenzene/hexamethylbenzene, 1/1. polymorph IV

Crystal data

C8N2Cl4·C12H18	Z = 2
Mr = 428.16	F(000) = 440
Triclinic, P1	Dx = 1.451 Mg m^−3
a = 7.4982 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0371 (3) Å	Cell parameters from 1500 reflections
c = 15.4538 (6) Å	θ = 2–25°
α = 85.080 (2)°	µ = 0.61 mm^−1
β = 81.795 (2)°	T = 174 K
γ = 71.168 (2)°	Deformed needle, yellow
V = 980.10 (5) Å^3	0.30 × 0.26 × 0.18 mm

Data collection

SMART diffractometer	3354 independent reflections
Radiation source: fine-focus sealed tube	1520 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
ω scans	θmax = 25.1°, θmin = 1.3°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995	h = −8→8
Tmin = 0.79, Tmax = 0.90	k = −10→10
5453 measured reflections	l = −18→16

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)] = 0.094	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.247	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ^2(Fo^2) + (0.137P)^2] where P = (Fo^2 + 2Fc^2)/3
3354 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.71 e Å^−3
0 restraints	Δρmin = −0.97 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	1.0407 (9)	0.6233 (8)	−0.0488 (5)	0.0306 (18)
C2	0.9681 (10)	0.6406 (7)	0.0375 (5)	0.0314 (18)
C3	0.9266 (9)	0.5220 (8)	0.0898 (5)	0.0319 (19)
C11	1.0761 (10)	0.7550 (9)	−0.0994 (5)	0.0297 (18)
N11	1.1039 (9)	0.8562 (7)	−0.1402 (5)	0.0491 (19)
Cl12	0.9253 (3)	0.8184 (2)	0.08411 (14)	0.0437 (6)
Cl13	0.8361 (3)	0.5374 (2)	0.19632 (13)	0.0433 (6)
C21	0.5418 (9)	0.8655 (7)	0.4557 (5)	0.0261 (17)
C22	0.5683 (10)	0.9989 (8)	0.4109 (5)	0.035 (2)
C23	0.5241 (10)	1.1351 (8)	0.4573 (5)	0.0333 (19)
C31	0.5863 (10)	0.7157 (8)	0.4116 (4)	0.0287 (18)
N31	0.6202 (10)	0.6150 (7)	0.3714 (5)	0.057 (2)
Cl32	0.6542 (3)	0.9935 (2)	0.30215 (13)	0.0449 (6)
Cl33	0.5525 (3)	1.3027 (2)	0.40495 (14)	0.0474 (7)
C41	0.5320 (11)	0.6285 (8)	−0.0468 (6)	0.038 (2)
C42	0.4608 (10)	0.6404 (8)	0.0413 (6)	0.038 (2)
C43	0.4314 (10)	0.5115 (9)	0.0887 (5)	0.037 (2)
C51	0.5684 (12)	0.7696 (9)	−0.0981 (6)	0.056 (3)
H51A	0.6281	0.7398	−0.1573	0.085*	0.50
H51B	0.6527	0.8063	−0.0686	0.085*	0.50
H51C	0.4476	0.8536	−0.1012	0.085*	0.50
H51D	0.5242	0.8600	−0.0608	0.085*	0.50
H51E	0.4996	0.7935	−0.1495	0.085*	0.50
H51F	0.7047	0.7462	−0.1169	0.085*	0.50
C52	0.4179 (13)	0.7942 (9)	0.0852 (6)	0.062 (3)
H52A	0.4822	0.7757	0.1380	0.092*	0.50
H52B	0.2806	0.8386	0.1014	0.092*	0.50
H52C	0.4634	0.8675	0.0447	0.092*	0.50
H52D	0.3353	0.8789	0.0514	0.092*	0.50
H52E	0.5368	0.8159	0.0880	0.092*	0.50
H52F	0.3541	0.7870	0.1446	0.092*	0.50
C53	0.3597 (12)	0.5188 (11)	0.1862 (5)	0.063 (3)
H53A	0.3482	0.4170	0.2084	0.094*	0.50
H53B	0.2353	0.5993	0.1953	0.094*	0.50
H53C	0.4496	0.5449	0.2176	0.094*	0.50
H53D	0.3406	0.6238	0.2058	0.094*	0.50
H53E	0.4534	0.4415	0.2189	0.094*	0.50
H53F	0.2391	0.4959	0.1966	0.094*	0.50
C61	0.0401 (10)	0.8498 (8)	0.4726 (6)	0.039 (2)
C62	0.0731 (10)	0.9639 (9)	0.4135 (5)	0.039 (2)
C63	0.0352 (10)	1.1162 (8)	0.4398 (5)	0.038 (2)
C71	0.0821 (13)	0.6845 (9)	0.4417 (7)	0.072 (3)
H71A	0.0348	0.6211	0.4883	0.108*	0.50
H71B	0.2194	0.6370	0.4271	0.108*	0.50
H71C	0.0189	0.6894	0.3897	0.108*	0.50
H71D	0.1473	0.6772	0.3818	0.108*	0.50
H71E	−0.0373	0.6614	0.4429	0.108*	0.50
H71F	0.1632	0.6089	0.4804	0.108*	0.50
C72	0.1551 (12)	0.9285 (11)	0.3178 (6)	0.067 (3)
H72A	0.1397	1.0269	0.2832	0.100*	0.50
H72B	0.0876	0.8674	0.2942	0.100*	0.50
H72C	0.2903	0.8684	0.3150	0.100*	0.50
H72D	0.2054	0.8149	0.3117	0.100*	0.50
H72E	0.2574	0.9744	0.3007	0.100*	0.50
H72F	0.0548	0.9734	0.2800	0.100*	0.50
C73	0.0677 (11)	1.2424 (10)	0.3763 (6)	0.058 (3)
H73A	0.0165	1.3434	0.4041	0.087*	0.50
H73B	0.0038	1.2461	0.3247	0.087*	0.50
H73C	0.2043	1.2201	0.3584	0.087*	0.50
H73D	0.1332	1.1964	0.3207	0.087*	0.50
H73E	0.1459	1.2936	0.4002	0.087*	0.50
H73F	−0.0546	1.3197	0.3664	0.087*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.019 (4)	0.034 (4)	0.039 (5)	−0.007 (3)	−0.004 (3)	−0.001 (4)
C2	0.024 (4)	0.026 (4)	0.051 (5)	−0.014 (3)	−0.012 (4)	−0.003 (4)
C3	0.019 (4)	0.027 (4)	0.052 (5)	−0.005 (3)	−0.017 (4)	0.000 (4)
C11	0.021 (4)	0.039 (5)	0.031 (4)	−0.013 (4)	−0.007 (3)	0.010 (4)
N11	0.048 (5)	0.043 (4)	0.065 (5)	−0.023 (4)	−0.020 (4)	0.008 (4)
Cl12	0.0471 (14)	0.0318 (11)	0.0579 (14)	−0.0185 (9)	−0.0097 (10)	−0.0025 (9)
Cl13	0.0456 (13)	0.0465 (13)	0.0426 (12)	−0.0220 (10)	−0.0043 (10)	0.0005 (10)
C21	0.025 (4)	0.021 (4)	0.036 (5)	−0.011 (3)	−0.008 (3)	0.000 (3)
C22	0.022 (5)	0.037 (4)	0.050 (5)	−0.011 (4)	−0.005 (4)	−0.012 (4)
C23	0.027 (4)	0.023 (4)	0.053 (5)	−0.012 (3)	−0.008 (4)	0.004 (4)
C31	0.031 (5)	0.029 (4)	0.024 (4)	−0.007 (4)	0.002 (3)	−0.008 (4)
N31	0.065 (6)	0.031 (4)	0.074 (6)	−0.017 (4)	−0.010 (4)	0.009 (4)
Cl32	0.0539 (14)	0.0463 (12)	0.0382 (12)	−0.0230 (10)	−0.0013 (10)	−0.0005 (9)
Cl33	0.0541 (14)	0.0305 (11)	0.0654 (15)	−0.0230 (10)	−0.0160 (11)	0.0086 (10)
C41	0.035 (5)	0.026 (4)	0.059 (6)	−0.014 (4)	−0.017 (4)	0.008 (4)
C42	0.030 (5)	0.028 (4)	0.060 (6)	−0.013 (4)	−0.011 (4)	−0.002 (4)
C43	0.033 (5)	0.046 (5)	0.040 (5)	−0.018 (4)	−0.014 (4)	−0.001 (4)
C51	0.045 (6)	0.043 (5)	0.089 (7)	−0.024 (4)	−0.026 (5)	0.024 (5)
C52	0.067 (7)	0.034 (5)	0.088 (7)	−0.013 (5)	−0.022 (6)	−0.018 (5)
C53	0.059 (6)	0.083 (7)	0.060 (6)	−0.038 (5)	−0.018 (5)	0.008 (5)
C61	0.032 (5)	0.025 (4)	0.067 (6)	−0.013 (4)	−0.024 (4)	0.001 (4)
C62	0.031 (5)	0.035 (4)	0.045 (5)	−0.002 (4)	−0.015 (4)	0.008 (4)
C63	0.032 (5)	0.032 (4)	0.051 (6)	−0.011 (4)	−0.018 (4)	0.017 (4)
C71	0.075 (8)	0.041 (5)	0.099 (8)	−0.009 (5)	−0.023 (6)	−0.021 (5)
C72	0.053 (6)	0.072 (7)	0.068 (7)	−0.005 (5)	−0.019 (5)	0.000 (5)
C73	0.033 (5)	0.065 (6)	0.080 (7)	−0.025 (5)	−0.013 (5)	0.023 (5)

Geometric parameters (Å, º)

C1—C2	1.368 (10)	C52—H52E	0.9800
C1—C3^i	1.441 (10)	C52—H52F	0.9800
C1—C11	1.444 (9)	C53—H53A	0.9800
C2—C3	1.377 (9)	C53—H53B	0.9800
C2—Cl12	1.733 (7)	C53—H53C	0.9800
C3—C1^i	1.441 (10)	C53—H53D	0.9800
C3—Cl13	1.688 (8)	C53—H53E	0.9800
C11—N11	1.125 (8)	C53—H53F	0.9800
C21—C23^ii	1.364 (10)	C61—C62	1.378 (10)
C21—C22	1.394 (9)	C61—C63^iv	1.409 (10)
C21—C31	1.487 (9)	C61—C71	1.529 (10)
C22—C23	1.399 (9)	C62—C63	1.397 (10)
C22—Cl32	1.711 (8)	C62—C72	1.536 (11)
C23—C21^ii	1.364 (10)	C63—C61^iv	1.409 (10)
C23—Cl33	1.716 (7)	C63—C73	1.497 (10)
C31—N31	1.087 (9)	C71—H71A	0.9800
C41—C42	1.389 (11)	C71—H71B	0.9800
C41—C43^iii	1.401 (10)	C71—H71C	0.9800
C41—C51	1.522 (10)	C71—H71D	0.9800
C42—C43	1.384 (10)	C71—H71E	0.9800
C42—C52	1.519 (10)	C71—H71F	0.9800
C43—C41^iii	1.401 (10)	C72—H72A	0.9800
C43—C53	1.525 (11)	C72—H72B	0.9800
C51—H51A	0.9800	C72—H72C	0.9800
C51—H51B	0.9800	C72—H72D	0.9800
C51—H51C	0.9800	C72—H72E	0.9800
C51—H51D	0.9800	C72—H72F	0.9800
C51—H51E	0.9800	C73—H73A	0.9800
C51—H51F	0.9800	C73—H73B	0.9800
C52—H52A	0.9800	C73—H73C	0.9800
C52—H52B	0.9800	C73—H73D	0.9800
C52—H52C	0.9800	C73—H73E	0.9800
C52—H52D	0.9800	C73—H73F	0.9800
C2—C1—C3^i	120.6 (7)	H53A—C53—H53E	56.3
C2—C1—C11	119.0 (7)	H53B—C53—H53E	141.1
C3^i—C1—C11	120.3 (7)	H53C—C53—H53E	56.3
C1—C2—C3	122.7 (6)	H53D—C53—H53E	109.5
C1—C2—Cl12	119.5 (6)	C43—C53—H53F	109.5
C3—C2—Cl12	117.8 (6)	H53A—C53—H53F	56.3
C2—C3—C1^i	116.6 (7)	H53B—C53—H53F	56.3
C2—C3—Cl13	124.6 (6)	H53C—C53—H53F	141.1
C1^i—C3—Cl13	118.7 (6)	H53D—C53—H53F	109.5
N11—C11—C1	178.7 (8)	H53E—C53—H53F	109.5
C23^ii—C21—C22	121.8 (6)	C62—C61—C63^iv	121.3 (7)
C23^ii—C21—C31	116.4 (6)	C62—C61—C71	119.0 (8)
C22—C21—C31	121.8 (6)	C63^iv—C61—C71	119.7 (7)
C21—C22—C23	118.3 (7)	C61—C62—C63	120.3 (7)
C21—C22—Cl32	120.2 (5)	C61—C62—C72	121.8 (7)
C23—C22—Cl32	121.5 (6)	C63—C62—C72	117.9 (7)
C21^ii—C23—C22	119.9 (6)	C62—C63—C61^iv	118.4 (7)
C21^ii—C23—Cl33	120.0 (6)	C62—C63—C73	121.2 (8)
C22—C23—Cl33	120.1 (6)	C61^iv—C63—C73	120.4 (7)
N31—C31—C21	172.5 (8)	C61—C71—H71A	109.5
C42—C41—C43^iii	120.5 (7)	C61—C71—H71B	109.5
C42—C41—C51	119.5 (7)	H71A—C71—H71B	109.5
C43^iii—C41—C51	120.0 (8)	C61—C71—H71C	109.5
C43—C42—C41	119.8 (7)	H71A—C71—H71C	109.5
C43—C42—C52	120.4 (8)	H71B—C71—H71C	109.5
C41—C42—C52	119.8 (7)	C61—C71—H71D	109.5
C42—C43—C41^iii	119.7 (7)	H71A—C71—H71D	141.1
C42—C43—C53	121.2 (7)	H71B—C71—H71D	56.3
C41^iii—C43—C53	119.1 (7)	H71C—C71—H71D	56.3
C41—C51—H51A	109.5	C61—C71—H71E	109.5
C41—C51—H51B	109.5	H71A—C71—H71E	56.3
H51A—C51—H51B	109.5	H71B—C71—H71E	141.1
C41—C51—H51C	109.5	H71C—C71—H71E	56.3
H51A—C51—H51C	109.5	H71D—C71—H71E	109.5
H51B—C51—H51C	109.5	C61—C71—H71F	109.5
C41—C51—H51D	109.5	H71A—C71—H71F	56.3
H51A—C51—H51D	141.1	H71B—C71—H71F	56.3
H51B—C51—H51D	56.3	H71C—C71—H71F	141.1
H51C—C51—H51D	56.3	H71D—C71—H71F	109.5
C41—C51—H51E	109.5	H71E—C71—H71F	109.5
H51A—C51—H51E	56.3	C62—C72—H72A	109.5
H51B—C51—H51E	141.1	C62—C72—H72B	109.5
H51C—C51—H51E	56.3	H72A—C72—H72B	109.5
H51D—C51—H51E	109.5	C62—C72—H72C	109.5
C41—C51—H51F	109.5	H72A—C72—H72C	109.5
H51A—C51—H51F	56.3	H72B—C72—H72C	109.5
H51B—C51—H51F	56.3	C62—C72—H72D	109.5
H51C—C51—H51F	141.1	H72A—C72—H72D	141.1
H51D—C51—H51F	109.5	H72B—C72—H72D	56.3
H51E—C51—H51F	109.5	H72C—C72—H72D	56.3
C42—C52—H52A	109.5	C62—C72—H72E	109.5
C42—C52—H52B	109.5	H72A—C72—H72E	56.3
H52A—C52—H52B	109.5	H72B—C72—H72E	141.1
C42—C52—H52C	109.5	H72C—C72—H72E	56.3
H52A—C52—H52C	109.5	H72D—C72—H72E	109.5
H52B—C52—H52C	109.5	C62—C72—H72F	109.5
C42—C52—H52D	109.5	H72A—C72—H72F	56.3
H52A—C52—H52D	141.1	H72B—C72—H72F	56.3
H52B—C52—H52D	56.3	H72C—C72—H72F	141.1
H52C—C52—H52D	56.3	H72D—C72—H72F	109.5
C42—C52—H52E	109.5	H72E—C72—H72F	109.5
H52A—C52—H52E	56.3	C63—C73—H73A	109.5
H52B—C52—H52E	141.1	C63—C73—H73B	109.5
H52C—C52—H52E	56.3	H73A—C73—H73B	109.5
H52D—C52—H52E	109.5	C63—C73—H73C	109.5
C42—C52—H52F	109.5	H73A—C73—H73C	109.5
H52A—C52—H52F	56.3	H73B—C73—H73C	109.5
H52B—C52—H52F	56.3	C63—C73—H73D	109.5
H52C—C52—H52F	141.1	H73A—C73—H73D	141.1
H52D—C52—H52F	109.5	H73B—C73—H73D	56.3
H52E—C52—H52F	109.5	H73C—C73—H73D	56.3
C43—C53—H53A	109.5	C63—C73—H73E	109.5
C43—C53—H53B	109.5	H73A—C73—H73E	56.3
H53A—C53—H53B	109.5	H73B—C73—H73E	141.1
C43—C53—H53C	109.5	H73C—C73—H73E	56.3
H53A—C53—H53C	109.5	H73D—C73—H73E	109.5
H53B—C53—H53C	109.5	C63—C73—H73F	109.5
C43—C53—H53D	109.5	H73A—C73—H73F	56.3
H53A—C53—H53D	141.1	H73B—C73—H73F	56.3
H53B—C53—H53D	56.3	H73C—C73—H73F	141.1
H53C—C53—H53D	56.3	H73D—C73—H73F	109.5
C43—C53—H53E	109.5	H73E—C73—H73F	109.5

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