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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102003348/bk0105sup1.cif
Contains datablocks ortho, metaI, metaII, paraI, paraII, paraIII, paraIV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102003348/bk0105orthosup2.hkl
Contains datablock ortho

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102003348/bk0105metaIsup3.hkl
Contains datablock metaI

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102003348/bk0105metaIIsup4.hkl
Contains datablock metaII

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102003348/bk0105paraIsup5.hkl
Contains datablock paraI

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102003348/bk0105paraIIsup6.hkl
Contains datablock paraII

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102003348/bk0105paraIIIsup7.hkl
Contains datablock paraIII

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102003348/bk0105paraIVsup8.hkl
Contains datablock paraIV

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768102003348/bk0105sup9.pdf
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768102003348/bk0105sup10.pdf
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768102003348/bk0105sup11.pdf
Supplementary material

CCDC references: 188116; 188117; 188118; 188119; 188120; 188121; 188122

Computing details top

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 top
Crystal data top
C12H18·C8Cl4N2F(000) = 880
Mr = 428.16Dx = 1.450 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 15.824 (3) ÅCell parameters from 1872 reflections
b = 9.1501 (15) Åθ = 3–27°
c = 13.894 (2) ŵ = 0.61 mm1
β = 102.879 (3)°T = 173 K
V = 1961.1 (6) Å3Needle, yellow
Z = 40.45 × 0.15 × 0.10 mm
Data collection top
Siemens SMART area-detector
diffractometer
2242 independent reflections
Radiation source: fine-focus sealed tube1604 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
SADABS; Sheldrick, 1996; Blessing, 1995
h = 1820
Tmin = 0.90, Tmax = 0.94k = 1111
6155 measured reflectionsl = 1618
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.062P)2]
where P = (Fo2 + 2Fc2)/3
2242 reflections(Δ/σ)max = 0.004
121 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.23 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl50.59865 (4)0.96463 (6)0.25827 (5)0.0452 (2)
Cl60.69849 (4)0.67011 (6)0.26371 (5)0.04175 (19)
N10.62706 (13)0.29419 (19)0.26325 (15)0.0387 (5)
C10.54454 (13)0.5385 (2)0.25327 (15)0.0262 (4)
C50.54438 (15)0.8025 (2)0.25328 (16)0.0301 (5)
C60.58908 (14)0.6707 (2)0.25629 (15)0.0283 (5)
C70.59078 (13)0.4013 (2)0.25794 (15)0.0275 (4)
C110.58932 (16)0.5064 (3)0.00754 (16)0.0410 (6)
C120.54047 (18)0.6352 (2)0.00111 (17)0.0417 (6)
C130.45132 (17)0.6284 (3)0.00753 (16)0.0418 (6)
C210.68711 (18)0.5135 (4)0.0165 (2)0.0701 (9)
H21A0.71550.43790.06240.105*
H21B0.70860.60990.04130.105*
H21C0.70000.49720.04850.105*
C220.5841 (3)0.7822 (3)0.0039 (2)0.0686 (9)
H22A0.63580.77010.03090.103*
H22B0.60080.82190.06310.103*
H22C0.54370.84950.04580.103*
C230.3979 (2)0.7673 (3)0.0147 (2)0.0646 (9)
H23A0.34710.75010.01330.097*
H23B0.37880.79600.08410.097*
H23C0.43320.84560.02220.097*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl50.0586 (4)0.0247 (3)0.0538 (4)0.0143 (3)0.0154 (3)0.0018 (2)
Cl60.0284 (3)0.0431 (3)0.0551 (4)0.0071 (2)0.0123 (3)0.0017 (3)
N10.0373 (11)0.0297 (11)0.0510 (13)0.0036 (8)0.0141 (10)0.0011 (9)
C10.0294 (10)0.0226 (10)0.0279 (11)0.0025 (8)0.0089 (9)0.0006 (8)
C50.0388 (12)0.0223 (10)0.0292 (11)0.0040 (8)0.0078 (10)0.0014 (8)
C60.0279 (11)0.0289 (11)0.0289 (11)0.0046 (8)0.0080 (9)0.0005 (9)
C70.0250 (10)0.0274 (11)0.0311 (11)0.0011 (9)0.0082 (9)0.0011 (9)
C110.0463 (14)0.0499 (15)0.0263 (12)0.0080 (12)0.0073 (10)0.0014 (10)
C120.0608 (16)0.0358 (12)0.0287 (12)0.0007 (12)0.0107 (11)0.0006 (10)
C130.0595 (16)0.0380 (13)0.0268 (12)0.0173 (12)0.0072 (11)0.0020 (10)
C210.0526 (18)0.102 (3)0.0548 (19)0.0031 (18)0.0108 (15)0.0107 (17)
C220.107 (3)0.0497 (16)0.0547 (18)0.0216 (18)0.0307 (18)0.0040 (14)
C230.092 (2)0.0535 (17)0.0475 (16)0.0383 (17)0.0135 (16)0.0023 (13)
Geometric parameters (Å, º) top
Cl5—C51.708 (2)C12—C221.516 (4)
Cl6—C61.711 (2)C13—C11ii1.391 (3)
N1—C71.130 (3)C13—C231.518 (3)
C1—C1i1.392 (4)C21—H21A0.9800
C1—C61.396 (3)C21—H21B0.9800
C1—C71.448 (3)C21—H21C0.9800
C5—C5i1.387 (5)C22—H22A0.9800
C5—C61.394 (3)C22—H22B0.9800
C11—C13ii1.391 (3)C22—H22C0.9800
C11—C121.399 (3)C23—H23A0.9800
C11—C211.526 (4)C23—H23B0.9800
C12—C131.395 (4)C23—H23C0.9800
C1i—C1—C6119.94 (12)C11—C21—H21A109.5
C1i—C1—C7119.82 (11)C11—C21—H21B109.5
C6—C1—C7120.24 (18)H21A—C21—H21B109.5
C5i—C5—C6120.11 (12)C11—C21—H21C109.5
C5i—C5—Cl5119.69 (8)H21A—C21—H21C109.5
C6—C5—Cl5120.20 (17)H21B—C21—H21C109.5
C5—C6—C1119.95 (19)C12—C22—H22A109.5
C5—C6—Cl6120.30 (16)C12—C22—H22B109.5
C1—C6—Cl6119.75 (16)H22A—C22—H22B109.5
N1—C7—C1178.8 (2)C12—C22—H22C109.5
C13ii—C11—C12120.0 (2)H22A—C22—H22C109.5
C13ii—C11—C21119.8 (2)H22B—C22—H22C109.5
C12—C11—C21120.1 (2)C13—C23—H23A109.5
C13—C12—C11120.0 (2)C13—C23—H23B109.5
C13—C12—C22119.8 (2)H23A—C23—H23B109.5
C11—C12—C22120.2 (3)C13—C23—H23C109.5
C11ii—C13—C12120.0 (2)H23A—C23—H23C109.5
C11ii—C13—C23119.5 (2)H23B—C23—H23C109.5
C12—C13—C23120.5 (2)
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+1, y+1, z.
(metaI) meta tetrachlorodicyanobenzene/hexamethylbenzene, 1/1 polymorph I top
Crystal data top
C12H18·C8Cl4N2Z = 1
Mr = 428.16F(000) = 220
Triclinic, P1Dx = 1.473 Mg m3
a = 7.5290 (12) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.9503 (14) ÅCell parameters from 776 reflections
c = 9.0513 (11) Åθ = 2.7–27.4°
α = 118.425 (3)°µ = 0.62 mm1
β = 109.414 (3)°T = 173 K
γ = 95.139 (3)°Thick plate, pale yellow
V = 482.80 (12) Å30.50 × 0.35 × 0.10 mm
Data collection top
Siemens SMART area-detectcor
diffractometer
2197 independent reflections
Radiation source: fine-focus sealed tube1784 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω scansθmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan
SADABS; Sheldrick, 1996; Blessing, 1995
h = 99
Tmin = 0.76, Tmax = 0.94k = 1111
4996 measured reflectionsl = 1111
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.072P)2 + 0.059P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.006
2197 reflectionsΔρmax = 0.27 e Å3
185 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.037 (8)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl120.50548 (16)0.20864 (14)0.15855 (14)0.0379 (3)0.50
Cl140.47371 (12)0.13216 (12)0.40184 (12)0.0339 (2)0.50
Cl150.49291 (15)0.26965 (13)0.16595 (15)0.0368 (3)0.50
Cl160.51453 (19)0.42166 (19)0.23267 (16)0.0364 (3)0.50
N110.5341 (4)0.2301 (4)0.5055 (4)0.0427 (6)0.50
N130.4777 (7)0.4770 (6)0.2992 (5)0.0405 (10)0.50
C10.5105 (6)0.1009 (7)0.1736 (7)0.0260 (9)0.50
C20.5011 (6)0.0772 (6)0.0674 (6)0.0288 (8)0.50
C30.4934 (6)0.1476 (6)0.1105 (7)0.0263 (9)0.50
C40.4908 (6)0.0414 (5)0.1812 (6)0.0225 (8)0.50
C50.4971 (5)0.1357 (5)0.0776 (5)0.0240 (7)0.50
C60.5054 (6)0.2039 (5)0.1000 (6)0.0237 (8)0.50
C110.5214 (5)0.1771 (4)0.3620 (5)0.0300 (7)0.50
C130.4853 (4)0.3316 (6)0.2180 (4)0.0321 (7)0.50
C210.0011 (2)0.11360 (19)0.0659 (2)0.0348 (3)
C220.01445 (19)0.06584 (19)0.18044 (18)0.0337 (3)
C230.01234 (19)0.17907 (18)0.11388 (19)0.0337 (3)
C310.0033 (3)0.2354 (2)0.1391 (3)0.0482 (4)
H31A0.06320.16360.27530.072*0.50
H31B0.13220.30560.09260.072*0.50
H31C0.08040.31570.09650.072*0.50
H31D0.05560.35970.03430.072*0.50
H31E0.13980.21760.21700.072*0.50
H31F0.07280.20760.21300.072*0.50
C320.0315 (3)0.1357 (2)0.3753 (2)0.0475 (4)
H32A0.07260.05390.41330.071*0.50
H32B0.12970.25350.46180.071*0.50
H32C0.09670.14500.37670.071*0.50
H32D0.00220.24770.42120.071*0.50
H32E0.05930.04810.37280.071*0.50
H32F0.16710.15660.45780.071*0.50
C330.0273 (3)0.3734 (2)0.2370 (2)0.0486 (4)
H33A0.07360.40600.36620.073*0.50
H33B0.12080.44870.22810.073*0.50
H33C0.10270.39060.19600.073*0.50
H33D0.01250.42420.16060.073*0.50
H33E0.05970.38150.29870.073*0.50
H33F0.16380.43960.33090.073*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl120.0483 (5)0.0393 (6)0.0347 (4)0.0147 (4)0.0202 (3)0.0241 (5)
Cl140.0416 (4)0.0363 (5)0.0219 (4)0.0119 (3)0.0173 (3)0.0120 (4)
Cl150.0485 (5)0.0367 (6)0.0352 (4)0.0166 (4)0.0222 (3)0.0228 (4)
Cl160.0447 (5)0.0318 (8)0.0295 (6)0.0131 (5)0.0175 (5)0.0130 (5)
N110.0494 (16)0.0443 (15)0.0329 (14)0.0141 (12)0.0170 (12)0.0201 (13)
N130.0492 (18)0.035 (2)0.039 (2)0.0136 (18)0.022 (2)0.0187 (19)
C10.0263 (14)0.023 (2)0.0261 (17)0.0056 (16)0.0109 (11)0.0123 (18)
C20.0296 (15)0.033 (2)0.0312 (18)0.0114 (14)0.0132 (11)0.0219 (19)
C30.0318 (16)0.025 (2)0.0262 (17)0.0109 (17)0.0140 (12)0.0147 (19)
C40.0229 (13)0.023 (2)0.0178 (14)0.0040 (15)0.0101 (9)0.0075 (18)
C50.0262 (14)0.029 (2)0.0211 (14)0.0098 (13)0.0112 (10)0.0156 (15)
C60.0243 (13)0.023 (2)0.0192 (15)0.0079 (15)0.0098 (10)0.0073 (17)
C110.0310 (15)0.0335 (16)0.0337 (18)0.0094 (11)0.0157 (13)0.0228 (14)
C130.0365 (16)0.0340 (19)0.0352 (19)0.0140 (13)0.0174 (12)0.0232 (19)
C210.0277 (7)0.0425 (7)0.0333 (7)0.0097 (5)0.0125 (6)0.0203 (6)
C220.0239 (7)0.0433 (7)0.0245 (6)0.0062 (5)0.0086 (5)0.0135 (6)
C230.0262 (7)0.0350 (7)0.0297 (7)0.0073 (5)0.0108 (5)0.0114 (6)
C310.0495 (10)0.0578 (10)0.0520 (10)0.0213 (8)0.0256 (8)0.0364 (9)
C320.0463 (9)0.0584 (10)0.0288 (7)0.0092 (7)0.0176 (7)0.0172 (7)
C330.0479 (9)0.0400 (8)0.0453 (9)0.0126 (7)0.0207 (8)0.0138 (7)
Geometric parameters (Å, º) top
Cl12—C21.726 (4)C23—C331.521 (2)
Cl14—C41.712 (4)C31—H31A0.9800
Cl15—C51.726 (4)C31—H31B0.9800
Cl16—C61.714 (4)C31—H31C0.9800
N11—C111.115 (4)C31—H31D0.9800
N13—C131.134 (5)C31—H31E0.9800
C1—C61.367 (5)C31—H31F0.9800
C1—C21.395 (6)C32—H32A0.9800
C1—C111.473 (6)C32—H32B0.9800
C2—C31.400 (6)C32—H32C0.9800
C3—C41.374 (5)C32—H32D0.9800
C3—C131.442 (6)C32—H32E0.9800
C4—C51.391 (5)C32—H32F0.9800
C5—C61.398 (6)C33—H33A0.9800
C21—C23i1.405 (2)C33—H33B0.9800
C21—C221.408 (2)C33—H33C0.9800
C21—C311.520 (2)C33—H33D0.9800
C22—C231.403 (2)C33—H33E0.9800
C22—C321.5180 (19)C33—H33F0.9800
C23—C21i1.405 (2)
C6—C1—C2119.4 (4)H31B—C31—H31F56.3
C6—C1—C11120.0 (4)H31C—C31—H31F141.1
C2—C1—C11120.5 (4)H31D—C31—H31F109.5
C1—C2—C3120.1 (3)H31E—C31—H31F109.5
C1—C2—Cl12119.8 (3)C22—C32—H32A109.5
C3—C2—Cl12120.2 (4)C22—C32—H32B109.5
C4—C3—C2119.6 (4)H32A—C32—H32B109.5
C4—C3—C13121.0 (4)C22—C32—H32C109.5
C2—C3—C13119.4 (4)H32A—C32—H32C109.5
C3—C4—C5120.8 (4)H32B—C32—H32C109.5
C3—C4—Cl14118.8 (3)C22—C32—H32D109.5
C5—C4—Cl14120.4 (3)H32A—C32—H32D141.1
C4—C5—C6118.8 (4)H32B—C32—H32D56.3
C4—C5—Cl15121.1 (3)H32C—C32—H32D56.3
C6—C5—Cl15120.2 (3)C22—C32—H32E109.5
C1—C6—C5121.3 (4)H32A—C32—H32E56.3
C1—C6—Cl16118.5 (4)H32B—C32—H32E141.1
C5—C6—Cl16120.3 (3)H32C—C32—H32E56.3
N11—C11—C1177.0 (4)H32D—C32—H32E109.5
N13—C13—C3178.1 (4)C22—C32—H32F109.5
C23i—C21—C22120.23 (13)H32A—C32—H32F56.3
C23i—C21—C31120.32 (13)H32B—C32—H32F56.3
C22—C21—C31119.45 (13)H32C—C32—H32F141.1
C23—C22—C21119.79 (13)H32D—C32—H32F109.5
C23—C22—C32120.41 (13)H32E—C32—H32F109.5
C21—C22—C32119.80 (14)C23—C33—H33A109.5
C22—C23—C21i119.98 (12)C23—C33—H33B109.5
C22—C23—C33120.12 (14)H33A—C33—H33B109.5
C21i—C23—C33119.90 (14)C23—C33—H33C109.5
C21—C31—H31A109.5H33A—C33—H33C109.5
C21—C31—H31B109.5H33B—C33—H33C109.5
H31A—C31—H31B109.5C23—C33—H33D109.5
C21—C31—H31C109.5H33A—C33—H33D141.1
H31A—C31—H31C109.5H33B—C33—H33D56.3
H31B—C31—H31C109.5H33C—C33—H33D56.3
C21—C31—H31D109.5C23—C33—H33E109.5
H31A—C31—H31D141.1H33A—C33—H33E56.3
H31B—C31—H31D56.3H33B—C33—H33E141.1
H31C—C31—H31D56.3H33C—C33—H33E56.3
C21—C31—H31E109.5H33D—C33—H33E109.5
H31A—C31—H31E56.3C23—C33—H33F109.5
H31B—C31—H31E141.1H33A—C33—H33F56.3
H31C—C31—H31E56.3H33B—C33—H33F56.3
H31D—C31—H31E109.5H33C—C33—H33F141.1
C21—C31—H31F109.5H33D—C33—H33F109.5
H31A—C31—H31F56.3H33E—C33—H33F109.5
Symmetry code: (i) x, y, z.
(metaII) meta tetrachlorodicyanobenzene/hexamethylbenzene, 1/1 polymorph II top
Crystal data top
C12H18·C8Cl4N2Z = 4
Mr = 428.16F(000) = 880
Triclinic, P1Dx = 1.467 Mg m3
a = 14.064 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.9554 (13) ÅCell parameters from 3897 reflections
c = 18.117 (3) Åθ = 2.7–27.2°
α = 118.407 (2)°µ = 0.62 mm1
β = 90.832 (3)°T = 173 K
γ = 76.460 (2)°Prism, yellow
V = 1938.8 (5) Å30.45 × 0.40 × 0.35 mm
Data collection top
Bruker SMART area-detector
diffractometer
8698 independent reflections
Radiation source: fine-focus sealed tube5502 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
SADABS; Sheldrick, 1996; Blessing, 1995
h = 1818
Tmin = 0.76, Tmax = 0.81k = 1111
19454 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.225H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.153P)2]
where P = (Fo2 + 2Fc2)/3
8698 reflections(Δ/σ)max = 0.027
542 parametersΔρmax = 1.27 e Å3
90 restraintsΔρmin = 0.63 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.24599 (19)0.6544 (4)0.79039 (15)0.0183 (6)0.8152 (10)
C20.24893 (19)0.8288 (4)0.84144 (16)0.0200 (6)0.8152 (10)
C30.25340 (19)0.8939 (4)0.92836 (15)0.0192 (6)0.8152 (10)
C40.25543 (18)0.7852 (3)0.96332 (15)0.0181 (6)0.8152 (10)
C50.25143 (18)0.6114 (3)0.91319 (16)0.0182 (6)0.8152 (10)
C60.24747 (18)0.5468 (3)0.82642 (16)0.0183 (6)0.8152 (10)
C70.2400 (3)0.5856 (4)0.6998 (2)0.0292 (4)0.8152 (10)
N10.23299 (18)0.5372 (3)0.63054 (14)0.0292 (4)0.8152 (10)
C80.2575 (2)1.0755 (4)0.98001 (18)0.0295 (4)0.8152 (10)
N30.2588 (2)1.2182 (4)1.01995 (15)0.0295 (4)0.8152 (10)
Cl20.24703 (6)0.96139 (11)0.79734 (5)0.0301 (2)0.8152 (10)
Cl40.26309 (5)0.86870 (9)1.06968 (4)0.0258 (2)0.8152 (10)
Cl50.25386 (6)0.47643 (10)0.95599 (5)0.0281 (2)0.8152 (10)
Cl60.24281 (6)0.33431 (10)0.76188 (4)0.0270 (2)0.8152 (10)
C110.25474 (19)0.8451 (4)0.45970 (16)0.0195 (6)0.8152 (10)
C120.25131 (19)0.6706 (3)0.40866 (16)0.0195 (6)0.8152 (10)
C130.24700 (19)0.6054 (4)0.32222 (16)0.0201 (6)0.8152 (10)
C140.24526 (18)0.7136 (3)0.28676 (15)0.0186 (6)0.8152 (10)
C150.24830 (19)0.8884 (3)0.33712 (16)0.0207 (6)0.8152 (10)
C160.25288 (18)0.9522 (3)0.42381 (16)0.0191 (6)0.8152 (10)
C170.2608 (2)0.9138 (4)0.55040 (19)0.0277 (4)0.8152 (10)
N110.26697 (18)0.9632 (3)0.61930 (14)0.0277 (4)0.8152 (10)
C180.2431 (2)0.4237 (4)0.27013 (18)0.0282 (4)0.8152 (10)
N130.2388 (2)0.2820 (4)0.23042 (15)0.0282 (4)0.8152 (10)
Cl120.25308 (6)0.53808 (11)0.45267 (5)0.0295 (2)0.8152 (10)
Cl140.23688 (5)0.63075 (9)0.18031 (4)0.0261 (2)0.8152 (10)
Cl150.24628 (6)1.02307 (10)0.29381 (5)0.0280 (2)0.8152 (10)
Cl160.25705 (6)1.16536 (10)0.48808 (4)0.0273 (2)0.8152 (10)
C210.00710 (17)0.1723 (3)0.05390 (15)0.0270 (5)
C220.00105 (17)0.1137 (3)0.03314 (15)0.0286 (6)
C230.00726 (16)0.0591 (3)0.08665 (14)0.0279 (6)
C310.0019 (2)0.2366 (4)0.06808 (18)0.0413 (7)
H31A0.02440.35840.02350.062*0.50
H31B0.03890.21070.11480.062*0.50
H31C0.06960.22050.08860.062*0.50
H31D0.02860.16800.12780.062*0.50
H31E0.04310.31570.03650.062*0.50
H31F0.06540.30590.06260.062*0.50
C320.0159 (2)0.3577 (4)0.11135 (17)0.0425 (7)
H32A0.04160.36540.16320.064*0.50
H32B0.04910.44060.12550.064*0.50
H32C0.06080.38700.08240.064*0.50
H32D0.00610.42990.08420.064*0.50
H32E0.08470.35470.12190.064*0.50
H32F0.02520.40830.16500.064*0.50
C330.0155 (2)0.1202 (4)0.18001 (16)0.0412 (7)
H33A0.04440.22090.20380.062*0.50
H33B0.05750.02420.18650.062*0.50
H33C0.05010.15500.20980.062*0.50
H33D0.00990.04580.19630.062*0.50
H33E0.02300.24250.21350.062*0.50
H33F0.08470.11170.19030.062*0.50
C410.00526 (17)0.1732 (3)0.55381 (15)0.0272 (5)
C420.00254 (17)0.1146 (3)0.46709 (15)0.0278 (6)
C430.00771 (16)0.0587 (3)0.58647 (14)0.0262 (5)
C510.0062 (2)0.2386 (4)0.43198 (19)0.0418 (7)
H51A0.02620.33020.46780.063*0.50
H51B0.07490.29310.43100.063*0.50
H51C0.02780.17310.37450.063*0.50
H51D0.04010.20070.38100.063*0.50
H51E0.06100.23780.41780.063*0.50
H51F0.04180.35780.47430.063*0.50
C520.0129 (2)0.3598 (4)0.61131 (18)0.0430 (7)
H52A0.03870.36820.66330.065*0.50
H52B0.05240.44160.62530.065*0.50
H52C0.05740.38980.58240.065*0.50
H52D0.00960.43160.58400.065*0.50
H52E0.08160.35820.62200.065*0.50
H52F0.02820.41000.66490.065*0.50
C530.0156 (2)0.1206 (4)0.67977 (16)0.0419 (7)
H53A0.03040.23550.70620.063*0.50
H53B0.06840.03570.68620.063*0.50
H53C0.04690.13050.70710.063*0.50
H53D0.00420.03230.69350.063*0.50
H53E0.03380.23210.71350.063*0.50
H53F0.08150.13730.69250.063*0.50
C610.49955 (16)0.6096 (3)0.21783 (15)0.0256 (5)
C620.50606 (16)0.6681 (3)0.30459 (15)0.0256 (5)
C630.50717 (16)0.5535 (3)0.33731 (14)0.0250 (5)
C640.50060 (17)0.3819 (3)0.28389 (15)0.0269 (5)
C650.49412 (16)0.3236 (3)0.19727 (15)0.0260 (5)
C660.49349 (16)0.4370 (3)0.16411 (14)0.0255 (5)
C710.4981 (2)0.7334 (4)0.18240 (18)0.0395 (7)
H71A0.56460.74660.17780.059*0.50
H71B0.45360.84840.22020.059*0.50
H71C0.47500.68510.12640.059*0.50
H71D0.43090.77350.17180.059*0.50
H71E0.54190.67170.12940.059*0.50
H71F0.52050.83500.22320.059*0.50
C720.5133 (2)0.8552 (4)0.36225 (17)0.0398 (7)
H72A0.53510.86570.41580.060*0.50
H72B0.44870.93740.37320.060*0.50
H72C0.56090.88290.33490.060*0.50
H72D0.49470.92500.33350.060*0.50
H72E0.58110.85330.37600.060*0.50
H72F0.46890.90770.41430.060*0.50
C730.5162 (2)0.6131 (4)0.42995 (16)0.0403 (7)
H73A0.50860.74030.46040.060*0.50
H73B0.58100.55280.43620.060*0.50
H73C0.46480.58480.45320.060*0.50
H73D0.52770.51170.43940.060*0.50
H73E0.45520.69920.46370.060*0.50
H73F0.57150.66710.44670.060*0.50
C740.5007 (2)0.2581 (4)0.31921 (19)0.0436 (8)
H74A0.46350.32400.37550.065*0.50
H74B0.56860.20530.32320.065*0.50
H74C0.47010.16530.28170.065*0.50
H74D0.53800.13900.27810.065*0.50
H74E0.43280.25770.33040.065*0.50
H74F0.53140.29780.37190.065*0.50
C750.4863 (2)0.1365 (4)0.13967 (18)0.0408 (7)
H75A0.47120.12270.08410.061*0.50
H75B0.43370.11350.16450.061*0.50
H75C0.54890.05310.13340.061*0.50
H75D0.49800.07020.17050.061*0.50
H75E0.53550.07940.09020.061*0.50
H75F0.42030.13980.12130.061*0.50
C760.4853 (2)0.3767 (4)0.07133 (16)0.0411 (7)
H76A0.48840.25100.04160.062*0.50
H76B0.53970.39740.04740.062*0.50
H76C0.42250.44270.06490.062*0.50
H76D0.47870.47640.06100.062*0.50
H76E0.42740.33000.05520.062*0.50
H76F0.54460.28470.03770.062*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)
Cl220.2410 (3)0.9676 (4)0.30103 (19)0.0280 (2)0.1848 (10)
Cl240.2652 (2)0.8685 (4)0.57146 (13)0.0277 (4)0.1848 (10)
Cl250.2589 (3)0.4745 (3)0.45677 (17)0.0295 (2)0.1848 (10)
Cl260.2471 (3)0.3343 (3)0.26303 (16)0.0282 (4)0.1848 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0201 (11)0.0209 (15)0.0110 (10)0.0022 (11)0.0027 (8)0.0066 (11)
C20.0217 (12)0.0207 (15)0.0163 (11)0.0031 (11)0.0033 (9)0.0089 (11)
C30.0209 (12)0.0203 (15)0.0145 (11)0.0059 (10)0.0031 (9)0.0064 (11)
C40.0185 (11)0.0178 (14)0.0104 (10)0.0009 (10)0.0036 (8)0.0026 (10)
C50.0195 (11)0.0188 (15)0.0150 (11)0.0016 (10)0.0038 (8)0.0085 (11)
C60.0210 (12)0.0123 (14)0.0142 (11)0.0011 (10)0.0022 (8)0.0019 (10)
C70.0393 (8)0.0262 (10)0.0168 (8)0.0078 (7)0.0020 (7)0.0066 (7)
N10.0393 (8)0.0262 (10)0.0168 (8)0.0078 (7)0.0020 (7)0.0066 (7)
C80.0434 (9)0.0205 (13)0.0182 (10)0.0059 (10)0.0034 (8)0.0052 (10)
N30.0434 (9)0.0205 (13)0.0182 (10)0.0059 (10)0.0034 (8)0.0052 (10)
Cl20.0431 (4)0.0287 (5)0.0243 (4)0.0097 (4)0.0004 (3)0.0172 (3)
Cl40.0352 (4)0.0278 (4)0.0106 (3)0.0074 (3)0.0004 (2)0.0066 (3)
Cl50.0419 (4)0.0218 (4)0.0219 (3)0.0067 (4)0.0019 (3)0.0120 (3)
Cl60.0376 (4)0.0167 (4)0.0197 (4)0.0078 (3)0.0001 (3)0.0029 (3)
C110.0198 (12)0.0206 (15)0.0124 (11)0.0040 (11)0.0035 (8)0.0040 (11)
C120.0215 (12)0.0154 (14)0.0170 (12)0.0022 (10)0.0027 (9)0.0052 (11)
C130.0215 (12)0.0181 (15)0.0177 (12)0.0048 (11)0.0036 (9)0.0063 (11)
C140.0179 (11)0.0200 (15)0.0118 (11)0.0033 (10)0.0029 (8)0.0035 (10)
C150.0238 (12)0.0190 (15)0.0173 (11)0.0013 (10)0.0023 (9)0.0090 (11)
C160.0219 (12)0.0128 (14)0.0142 (11)0.0018 (10)0.0022 (9)0.0011 (10)
C170.0367 (8)0.0262 (10)0.0168 (8)0.0089 (8)0.0010 (7)0.0074 (6)
N110.0367 (8)0.0262 (10)0.0168 (8)0.0089 (8)0.0010 (7)0.0074 (6)
C180.0395 (9)0.0233 (12)0.0175 (9)0.0114 (9)0.0017 (7)0.0050 (10)
N130.0395 (9)0.0233 (12)0.0175 (9)0.0114 (9)0.0017 (7)0.0050 (10)
Cl120.0423 (4)0.0278 (5)0.0242 (4)0.0093 (4)0.0008 (3)0.0169 (3)
Cl140.0364 (4)0.0274 (4)0.0097 (3)0.0077 (3)0.0008 (3)0.0053 (3)
Cl150.0416 (4)0.0229 (4)0.0220 (3)0.0082 (3)0.0014 (3)0.0128 (3)
Cl160.0390 (4)0.0159 (4)0.0198 (4)0.0088 (3)0.0009 (3)0.0023 (3)
C210.0237 (12)0.0254 (14)0.0245 (12)0.0064 (10)0.0005 (9)0.0061 (11)
C220.0235 (12)0.0313 (15)0.0265 (13)0.0008 (10)0.0022 (9)0.0133 (11)
C230.0195 (11)0.0359 (15)0.0181 (12)0.0033 (10)0.0022 (9)0.0068 (11)
C310.0421 (16)0.0433 (18)0.0419 (16)0.0045 (14)0.0027 (12)0.0260 (15)
C320.0435 (17)0.0324 (17)0.0348 (16)0.0099 (13)0.0021 (12)0.0031 (13)
C330.0435 (16)0.052 (2)0.0216 (13)0.0154 (14)0.0036 (11)0.0116 (14)
C410.0241 (12)0.0273 (14)0.0237 (12)0.0064 (10)0.0032 (9)0.0073 (11)
C420.0246 (12)0.0329 (15)0.0251 (12)0.0033 (10)0.0044 (9)0.0152 (11)
C430.0192 (11)0.0356 (14)0.0182 (11)0.0055 (10)0.0030 (9)0.0094 (11)
C510.0423 (16)0.0458 (19)0.0430 (17)0.0037 (14)0.0057 (12)0.0290 (16)
C520.0454 (17)0.0343 (17)0.0358 (16)0.0131 (13)0.0010 (12)0.0051 (14)
C530.0419 (16)0.056 (2)0.0216 (13)0.0140 (14)0.0031 (11)0.0137 (14)
C610.0224 (11)0.0278 (13)0.0247 (12)0.0038 (9)0.0019 (9)0.0123 (11)
C620.0206 (12)0.0258 (14)0.0255 (12)0.0038 (10)0.0013 (9)0.0094 (11)
C630.0182 (11)0.0336 (14)0.0187 (11)0.0041 (9)0.0015 (8)0.0101 (10)
C640.0228 (12)0.0308 (14)0.0279 (13)0.0045 (10)0.0022 (9)0.0159 (11)
C650.0211 (11)0.0230 (13)0.0271 (12)0.0028 (10)0.0014 (9)0.0080 (11)
C660.0179 (11)0.0335 (14)0.0196 (12)0.0034 (9)0.0011 (9)0.0100 (10)
C710.0424 (16)0.0408 (18)0.0434 (16)0.0024 (13)0.0020 (12)0.0303 (15)
C720.0419 (16)0.0311 (16)0.0338 (15)0.0119 (13)0.0002 (12)0.0049 (13)
C730.0422 (16)0.057 (2)0.0220 (13)0.0159 (14)0.0008 (11)0.0177 (14)
C740.0472 (17)0.0428 (19)0.0474 (17)0.0022 (14)0.0054 (13)0.0311 (16)
C750.0425 (17)0.0301 (16)0.0383 (16)0.0116 (13)0.0014 (12)0.0067 (13)
C760.0395 (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)
Cl220.0416 (4)0.0229 (4)0.0220 (3)0.0082 (3)0.0014 (3)0.0128 (3)
Cl240.0367 (8)0.0262 (10)0.0168 (8)0.0089 (8)0.0010 (7)0.0074 (6)
Cl250.0423 (4)0.0278 (5)0.0242 (4)0.0093 (4)0.0008 (3)0.0169 (3)
Cl260.0395 (9)0.0233 (12)0.0175 (9)0.0114 (9)0.0017 (7)0.0050 (10)
Geometric parameters (Å, º) top
C1—C61.394 (4)C53—H53F0.9800
C1—C21.397 (4)C61—C661.404 (3)
C1—C71.462 (4)C61—C621.410 (3)
C2—C31.402 (3)C61—C711.519 (3)
C2—Cl21.714 (3)C62—C631.406 (3)
C3—C41.387 (4)C62—C721.524 (3)
C3—C81.455 (4)C63—C641.398 (3)
C4—C51.394 (4)C63—C731.513 (3)
C4—Cl41.716 (2)C64—C651.408 (3)
C5—C61.399 (3)C64—C741.521 (4)
C5—Cl51.713 (3)C65—C661.403 (3)
C6—Cl61.713 (3)C65—C751.526 (3)
C7—N11.128 (4)C66—C761.513 (3)
C8—N31.135 (4)C71—H71A0.9800
C11—C161.387 (4)C71—H71B0.9800
C11—C121.400 (4)C71—H71C0.9800
C11—C171.465 (4)C71—H71D0.9800
C12—C131.393 (3)C71—H71E0.9800
C12—Cl121.712 (3)C71—H71F0.9800
C13—C141.390 (4)C72—H72A0.9800
C13—C181.456 (4)C72—H72B0.9800
C14—C151.399 (4)C72—H72C0.9800
C14—Cl141.719 (3)C72—H72D0.9800
C15—C161.399 (3)C72—H72E0.9800
C15—Cl151.719 (3)C72—H72F0.9800
C16—Cl161.714 (3)C73—H73A0.9800
C17—N111.118 (4)C73—H73B0.9800
C18—N131.139 (4)C73—H73C0.9800
C21—C231.397 (4)C73—H73D0.9800
C21—C221.414 (3)C73—H73E0.9800
C21—C321.518 (4)C73—H73F0.9800
C22—C23i1.415 (4)C74—H74A0.9800
C22—C311.510 (3)C74—H74B0.9800
C23—C22i1.415 (4)C74—H74C0.9800
C23—C331.522 (3)C74—H74D0.9800
C31—H31A0.9800C74—H74E0.9800
C31—H31B0.9800C74—H74F0.9800
C31—H31C0.9800C75—H75A0.9800
C31—H31D0.9800C75—H75B0.9800
C31—H31E0.9800C75—H75C0.9800
C31—H31F0.9800C75—H75D0.9800
C32—H32A0.9800C75—H75E0.9800
C32—H32B0.9800C75—H75F0.9800
C32—H32C0.9800C76—H76A0.9800
C32—H32D0.9800C76—H76B0.9800
C32—H32E0.9800C76—H76C0.9800
C32—H32F0.9800C76—H76D0.9800
C33—H33A0.9800C76—H76E0.9800
C33—H33B0.9800C76—H76F0.9800
C33—H33C0.9800C1'—C6'1.393 (4)
C33—H33D0.9800C1'—C2'1.397 (4)
C33—H33E0.9800C1'—C7'1.462 (4)
C33—H33F0.9800C2'—C3'1.401 (3)
C41—C431.401 (4)C2'—Cl2'1.714 (3)
C41—C421.412 (3)C3'—C4'1.387 (4)
C41—C521.521 (4)C3'—C8'1.455 (4)
C42—C43ii1.405 (4)C4'—C5'1.394 (4)
C42—C511.512 (3)C4'—Cl4'1.716 (3)
C43—C42ii1.405 (4)C5'—C6'1.399 (3)
C43—C531.519 (3)C5'—Cl5'1.713 (3)
C51—H51A0.9800C6'—Cl6'1.712 (3)
C51—H51B0.9800C7'—N1'1.128 (4)
C51—H51C0.9800C8'—N3'1.135 (4)
C51—H51D0.9800C11'—C16'1.387 (4)
C51—H51E0.9800C11'—C12'1.400 (4)
C51—H51F0.9800C11'—C17'1.465 (4)
C52—H52A0.9801C12'—C13'1.393 (4)
C52—H52B0.9801C12'—Cl221.711 (3)
C52—H52C0.9801C13'—C14'1.391 (4)
C52—H52D0.9801C13'—C18'1.457 (4)
C52—H52E0.9801C14'—C15'1.398 (4)
C52—H52F0.9801C14'—Cl241.719 (3)
C53—H53A0.9800C15'—C16'1.400 (4)
C53—H53B0.9800C15'—Cl251.719 (3)
C53—H53C0.9800C16'—Cl261.714 (3)
C53—H53D0.9800C17'—N11'1.118 (4)
C53—H53E0.9800C18'—N13'1.139 (4)
C6—C1—C2119.7 (2)C66—C61—C62120.0 (2)
C6—C1—C7120.1 (2)C66—C61—C71119.8 (2)
C2—C1—C7120.2 (3)C62—C61—C71120.2 (2)
C1—C2—C3119.7 (2)C63—C62—C61120.1 (2)
C1—C2—Cl2119.8 (2)C63—C62—C72120.3 (2)
C3—C2—Cl2120.5 (2)C61—C62—C72119.6 (2)
C4—C3—C2120.0 (2)C64—C63—C62119.9 (2)
C4—C3—C8121.3 (2)C64—C63—C73119.4 (2)
C2—C3—C8118.6 (3)C62—C63—C73120.7 (2)
C3—C4—C5120.8 (2)C63—C64—C65120.0 (2)
C3—C4—Cl4118.7 (2)C63—C64—C74120.1 (2)
C5—C4—Cl4120.5 (2)C65—C64—C74120.0 (2)
C4—C5—C6118.9 (2)C66—C65—C64120.4 (2)
C4—C5—Cl5121.03 (19)C66—C65—C75120.1 (2)
C6—C5—Cl5120.0 (2)C64—C65—C75119.5 (2)
C1—C6—C5120.9 (2)C65—C66—C61119.6 (2)
C1—C6—Cl6118.3 (2)C65—C66—C76121.0 (2)
C5—C6—Cl6120.9 (2)C61—C66—C76119.4 (2)
N1—C7—C1177.8 (4)C61—C71—H71A109.5
N3—C8—C3178.6 (4)C61—C71—H71B109.5
C16—C11—C12119.6 (2)H71A—C71—H71B109.5
C16—C11—C17120.2 (2)C61—C71—H71C109.5
C12—C11—C17120.1 (3)H71A—C71—H71C109.5
C13—C12—C11119.8 (2)H71B—C71—H71C109.5
C13—C12—Cl12120.4 (2)C61—C71—H71D109.5
C11—C12—Cl12119.8 (2)H71A—C71—H71D141.1
C14—C13—C12120.2 (2)H71B—C71—H71D56.3
C14—C13—C18120.8 (2)H71C—C71—H71D56.3
C12—C13—C18119.1 (3)C61—C71—H71E109.5
C13—C14—C15120.6 (2)H71A—C71—H71E56.3
C13—C14—Cl14119.1 (2)H71B—C71—H71E141.1
C15—C14—Cl14120.4 (2)H71C—C71—H71E56.3
C16—C15—C14118.7 (2)H71D—C71—H71E109.5
C16—C15—Cl15120.4 (2)C61—C71—H71F109.5
C14—C15—Cl15120.9 (2)H71A—C71—H71F56.3
C11—C16—C15121.1 (2)H71B—C71—H71F56.3
C11—C16—Cl16118.5 (2)H71C—C71—H71F141.1
C15—C16—Cl16120.4 (2)H71D—C71—H71F109.5
N11—C17—C11178.6 (3)H71E—C71—H71F109.5
N13—C18—C13178.8 (3)C62—C72—H72A109.5
C23—C21—C22120.3 (2)C62—C72—H72B109.5
C23—C21—C32120.1 (2)H72A—C72—H72B109.5
C22—C21—C32119.7 (3)C62—C72—H72C109.5
C21—C22—C23i119.6 (2)H72A—C72—H72C109.5
C21—C22—C31119.9 (2)H72B—C72—H72C109.5
C23i—C22—C31120.5 (2)C62—C72—H72D109.5
C21—C23—C22i120.1 (2)H72A—C72—H72D141.1
C21—C23—C33120.6 (2)H72B—C72—H72D56.3
C22i—C23—C33119.3 (2)H72C—C72—H72D56.3
C22—C31—H31A109.5C62—C72—H72E109.5
C22—C31—H31B109.5H72A—C72—H72E56.3
H31A—C31—H31B109.5H72B—C72—H72E141.1
C22—C31—H31C109.5H72C—C72—H72E56.3
H31A—C31—H31C109.5H72D—C72—H72E109.5
H31B—C31—H31C109.5C62—C72—H72F109.5
C22—C31—H31D109.5H72A—C72—H72F56.3
H31A—C31—H31D141.1H72B—C72—H72F56.3
H31B—C31—H31D56.3H72C—C72—H72F141.1
H31C—C31—H31D56.3H72D—C72—H72F109.5
C22—C31—H31E109.5H72E—C72—H72F109.5
H31A—C31—H31E56.3C63—C73—H73A109.5
H31B—C31—H31E141.1C63—C73—H73B109.5
H31C—C31—H31E56.3H73A—C73—H73B109.5
H31D—C31—H31E109.5C63—C73—H73C109.5
C22—C31—H31F109.5H73A—C73—H73C109.5
H31A—C31—H31F56.3H73B—C73—H73C109.5
H31B—C31—H31F56.3C63—C73—H73D109.5
H31C—C31—H31F141.1H73A—C73—H73D141.1
H31D—C31—H31F109.5H73B—C73—H73D56.3
H31E—C31—H31F109.5H73C—C73—H73D56.3
C21—C32—H32A109.5C63—C73—H73E109.5
C21—C32—H32B109.5H73A—C73—H73E56.3
H32A—C32—H32B109.5H73B—C73—H73E141.1
C21—C32—H32C109.5H73C—C73—H73E56.3
H32A—C32—H32C109.5H73D—C73—H73E109.5
H32B—C32—H32C109.5C63—C73—H73F109.5
C21—C32—H32D109.5H73A—C73—H73F56.3
H32A—C32—H32D141.1H73B—C73—H73F56.3
H32B—C32—H32D56.3H73C—C73—H73F141.1
H32C—C32—H32D56.3H73D—C73—H73F109.5
C21—C32—H32E109.5H73E—C73—H73F109.5
H32A—C32—H32E56.3C64—C74—H74A109.5
H32B—C32—H32E141.1C64—C74—H74B109.5
H32C—C32—H32E56.3H74A—C74—H74B109.5
H32D—C32—H32E109.5C64—C74—H74C109.5
C21—C32—H32F109.5H74A—C74—H74C109.5
H32A—C32—H32F56.3H74B—C74—H74C109.5
H32B—C32—H32F56.3C64—C74—H74D109.5
H32C—C32—H32F141.1H74A—C74—H74D141.1
H32D—C32—H32F109.5H74B—C74—H74D56.3
H32E—C32—H32F109.5H74C—C74—H74D56.3
C23—C33—H33A109.5C64—C74—H74E109.5
C23—C33—H33B109.5H74A—C74—H74E56.3
H33A—C33—H33B109.5H74B—C74—H74E141.1
C23—C33—H33C109.5H74C—C74—H74E56.3
H33A—C33—H33C109.5H74D—C74—H74E109.5
H33B—C33—H33C109.5C64—C74—H74F109.5
C23—C33—H33D109.5H74A—C74—H74F56.3
H33A—C33—H33D141.1H74B—C74—H74F56.3
H33B—C33—H33D56.3H74C—C74—H74F141.1
H33C—C33—H33D56.3H74D—C74—H74F109.5
C23—C33—H33E109.5H74E—C74—H74F109.5
H33A—C33—H33E56.3C65—C75—H75A109.5
H33B—C33—H33E141.1C65—C75—H75B109.5
H33C—C33—H33E56.3H75A—C75—H75B109.5
H33D—C33—H33E109.5C65—C75—H75C109.5
C23—C33—H33F109.5H75A—C75—H75C109.5
H33A—C33—H33F56.3H75B—C75—H75C109.5
H33B—C33—H33F56.3C65—C75—H75D109.5
H33C—C33—H33F141.1H75A—C75—H75D141.1
H33D—C33—H33F109.5H75B—C75—H75D56.3
H33E—C33—H33F109.5H75C—C75—H75D56.3
C43—C41—C42120.0 (2)C65—C75—H75E109.5
C43—C41—C52120.1 (2)H75A—C75—H75E56.3
C42—C41—C52119.8 (3)H75B—C75—H75E141.1
C43ii—C42—C41120.0 (2)H75C—C75—H75E56.3
C43ii—C42—C51120.0 (2)H75D—C75—H75E109.5
C41—C42—C51120.0 (2)C65—C75—H75F109.5
C41—C43—C42ii120.0 (2)H75A—C75—H75F56.3
C41—C43—C53120.5 (2)H75B—C75—H75F56.3
C42ii—C43—C53119.5 (2)H75C—C75—H75F141.1
C42—C51—H51A109.5H75D—C75—H75F109.5
C42—C51—H51B109.5H75E—C75—H75F109.5
H51A—C51—H51B109.5C66—C76—H76A109.5
C42—C51—H51C109.5C66—C76—H76B109.5
H51A—C51—H51C109.5H76A—C76—H76B109.5
H51B—C51—H51C109.5C66—C76—H76C109.5
C42—C51—H51D109.5H76A—C76—H76C109.5
H51A—C51—H51D141.1H76B—C76—H76C109.5
H51B—C51—H51D56.3C66—C76—H76D109.5
H51C—C51—H51D56.3H76A—C76—H76D141.1
C42—C51—H51E109.5H76B—C76—H76D56.3
H51A—C51—H51E56.3H76C—C76—H76D56.3
H51B—C51—H51E141.1C66—C76—H76E109.5
H51C—C51—H51E56.3H76A—C76—H76E56.3
H51D—C51—H51E109.5H76B—C76—H76E141.1
C42—C51—H51F109.5H76C—C76—H76E56.3
H51A—C51—H51F56.3H76D—C76—H76E109.5
H51B—C51—H51F56.3C66—C76—H76F109.5
H51C—C51—H51F141.1H76A—C76—H76F56.3
H51D—C51—H51F109.5H76B—C76—H76F56.3
H51E—C51—H51F109.5H76C—C76—H76F141.1
C41—C52—H52A109.5H76D—C76—H76F109.5
C41—C52—H52B109.5H76E—C76—H76F109.5
H52A—C52—H52B109.5C6'—C1'—C2'119.7 (2)
C41—C52—H52C109.5C6'—C1'—C7'120.2 (3)
H52A—C52—H52C109.5C2'—C1'—C7'120.2 (3)
H52B—C52—H52C109.5C1'—C2'—C3'119.7 (2)
C41—C52—H52D109.5C1'—C2'—Cl2'119.8 (2)
H52A—C52—H52D141.0C3'—C2'—Cl2'120.5 (2)
H52B—C52—H52D56.2C4'—C3'—C2'120.1 (3)
H52C—C52—H52D56.2C4'—C3'—C8'121.3 (3)
C41—C52—H52E109.5C2'—C3'—C8'118.6 (3)
H52A—C52—H52E56.2C3'—C4'—C5'120.8 (2)
H52B—C52—H52E141.0C3'—C4'—Cl4'118.6 (2)
H52C—C52—H52E56.2C5'—C4'—Cl4'120.6 (2)
H52D—C52—H52E109.5C4'—C5'—C6'118.9 (2)
C41—C52—H52F109.5C4'—C5'—Cl5'121.2 (2)
H52A—C52—H52F56.2C6'—C5'—Cl5'119.9 (2)
H52B—C52—H52F56.2C1'—C6'—C5'120.9 (2)
H52C—C52—H52F141.0C1'—C6'—Cl6'118.4 (2)
H52D—C52—H52F109.5C5'—C6'—Cl6'120.7 (2)
H52E—C52—H52F109.5N1'—C7'—C1'179.6 (8)
C43—C53—H53A109.5N3'—C8'—C3'178.4 (7)
C43—C53—H53B109.5C16'—C11'—C12'119.6 (2)
H53A—C53—H53B109.5C16'—C11'—C17'120.3 (3)
C43—C53—H53C109.5C12'—C11'—C17'120.1 (3)
H53A—C53—H53C109.5C13'—C12'—C11'119.8 (3)
H53B—C53—H53C109.5C13'—C12'—Cl22120.4 (2)
C43—C53—H53D109.5C11'—C12'—Cl22119.8 (2)
H53A—C53—H53D141.1C14'—C13'—C12'120.2 (3)
H53B—C53—H53D56.3C14'—C13'—C18'120.7 (3)
H53C—C53—H53D56.3C12'—C13'—C18'119.1 (3)
C43—C53—H53E109.5C13'—C14'—C15'120.6 (2)
H53A—C53—H53E56.3C13'—C14'—Cl24119.0 (2)
H53B—C53—H53E141.1C15'—C14'—Cl24120.4 (2)
H53C—C53—H53E56.3C14'—C15'—C16'118.7 (2)
H53D—C53—H53E109.5C14'—C15'—Cl25121.0 (2)
C43—C53—H53F109.5C16'—C15'—Cl25120.3 (2)
H53A—C53—H53F56.3C11'—C16'—C15'121.1 (2)
H53B—C53—H53F56.3C11'—C16'—Cl26118.6 (2)
H53C—C53—H53F141.1C15'—C16'—Cl26120.3 (2)
H53D—C53—H53F109.5N11'—C17'—C11'179.7 (6)
H53E—C53—H53F109.5N13'—C18'—C13'177.8 (7)
Symmetry codes: (i) x, y, z; (ii) x, y, z+1.
(paraI) para tetrachlorodicyanobenzene/hexamethylbenzene, 1/1 polymorph I top
Crystal data top
C12H18·C8Cl4N2Z = 1
Mr = 428.16F(000) = 220
Triclinic, P1Dx = 1.494 Mg m3
a = 7.513 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.615 (3) ÅCell parameters from 24 reflections
c = 9.029 (3) Åθ = 11–28°
α = 114.24 (3)°µ = 0.63 mm1
β = 113.30 (2)°T = 189 K
γ = 91.92 (3)°Sword-shaped, yellow
V = 475.8 (3) Å30.50 × 0.35 × 0.15 mm
Data collection top
CAD-4
diffractometer
2324 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.074
Graphite monochromatorθmax = 30.0°, θmin = 2.7°
ω–two θ scansh = 104
Absorption correction: empirical (using intensity measurements)
DIFABS, Walker, N. and Stuart, D. (1983) Acta Cryst. A39, 158-166.
k = 1212
Tmin = 0.75, Tmax = 0.91l = 1212
4293 measured reflections3 standard reflections every 60 min min
2775 independent reflections intensity decay: less than 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.074H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.212 w = 1/[σ2(Fo2) + (0.098P)2 + 0.96P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
2775 reflectionsΔρmax = 0.57 e Å3
122 parametersΔρmin = 0.65 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.09 (2)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.0391 (4)0.0988 (4)0.0765 (4)0.0190 (5)
C20.0801 (4)0.1798 (4)0.1069 (4)0.0195 (5)
C30.0403 (4)0.0797 (4)0.1829 (4)0.0192 (5)
C110.0763 (5)0.2024 (4)0.1565 (4)0.0231 (6)
N110.1016 (5)0.2841 (4)0.2219 (4)0.0314 (6)
Cl120.17471 (14)0.40092 (10)0.23184 (11)0.0321 (3)
Cl130.09077 (12)0.17518 (10)0.40714 (10)0.0265 (3)
C210.4191 (4)0.8209 (4)0.1203 (4)0.0219 (6)
C220.4591 (4)0.9372 (4)0.1829 (4)0.0212 (6)
C230.5411 (4)1.1143 (4)0.0630 (4)0.0213 (6)
C310.3321 (6)0.6276 (5)0.2496 (5)0.0322 (7)
H31A0.37310.59430.34430.048*0.50
H31B0.18920.60450.30210.048*0.50
H31C0.37870.56130.18430.048*0.50
H31D0.25430.57910.20950.048*0.50
H31E0.43810.56890.25170.048*0.50
H31F0.24860.61210.36950.048*0.50
C320.4074 (6)0.8658 (5)0.3836 (5)0.0334 (8)
H32A0.29840.76440.45430.050*0.50
H32B0.52130.83400.40160.050*0.50
H32C0.37010.95390.42130.050*0.50
H32D0.49480.93720.39710.050*0.50
H32E0.27190.86750.44990.050*0.50
H32F0.42310.74770.43020.050*0.50
C330.5876 (5)1.2381 (5)0.1296 (5)0.0311 (7)
H33A0.59841.35600.04660.047*0.50
H33B0.48271.20800.24780.047*0.50
H33C0.71131.22890.13670.047*0.50
H33D0.59651.17260.24080.047*0.50
H33E0.71231.32060.03960.047*0.50
H33F0.48361.29970.15070.047*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0176 (12)0.0244 (13)0.0205 (12)0.0050 (10)0.0108 (10)0.0130 (11)
C20.0189 (13)0.0193 (13)0.0206 (13)0.0019 (10)0.0101 (10)0.0084 (11)
C30.0198 (13)0.0244 (13)0.0180 (12)0.0072 (10)0.0118 (10)0.0107 (11)
C110.0230 (14)0.0259 (14)0.0246 (14)0.0046 (11)0.0131 (12)0.0130 (12)
N110.0374 (16)0.0327 (15)0.0326 (14)0.0071 (12)0.0185 (13)0.0200 (13)
Cl120.0437 (5)0.0221 (4)0.0287 (4)0.0000 (3)0.0183 (4)0.0087 (3)
Cl130.0319 (4)0.0300 (4)0.0183 (4)0.0048 (3)0.0133 (3)0.0098 (3)
C210.0175 (13)0.0227 (14)0.0257 (14)0.0019 (10)0.0094 (11)0.0119 (12)
C220.0179 (13)0.0266 (14)0.0225 (13)0.0049 (10)0.0096 (11)0.0138 (11)
C230.0155 (12)0.0257 (14)0.0265 (14)0.0030 (10)0.0088 (11)0.0163 (12)
C310.0342 (18)0.0245 (15)0.0329 (17)0.0018 (13)0.0153 (15)0.0091 (13)
C320.0340 (18)0.042 (2)0.0251 (15)0.0036 (15)0.0134 (14)0.0165 (15)
C330.0307 (17)0.0347 (17)0.0391 (18)0.0041 (13)0.0154 (14)0.0274 (15)
Geometric parameters (Å, º) top
C1—C3i1.384 (4)C31—H31C0.9600
C1—C21.399 (4)C31—H31D0.9600
C1—C111.439 (4)C31—H31E0.9600
C2—C31.391 (4)C31—H31F0.9600
C2—Cl121.708 (3)C32—H32A0.9600
C3—C1i1.384 (4)C32—H32B0.9600
C3—Cl131.710 (3)C32—H32C0.9600
C11—N111.141 (4)C32—H32D0.9600
C21—C23ii1.407 (4)C32—H32E0.9600
C21—C221.412 (4)C32—H32F0.9600
C21—C311.513 (5)C33—H33A0.9600
C22—C231.391 (4)C33—H33B0.9600
C22—C321.525 (4)C33—H33C0.9600
C23—C21ii1.407 (4)C33—H33D0.9600
C23—C331.513 (4)C33—H33E0.9600
C31—H31A0.9600C33—H33F0.9600
C31—H31B0.9600
C3i—C1—C2120.8 (3)C22—C32—H32B109.5
C3i—C1—C11119.5 (3)H32A—C32—H32B109.5
C2—C1—C11119.7 (3)C22—C32—H32C109.5
C3—C2—C1119.5 (3)H32A—C32—H32C109.5
C3—C2—Cl12121.4 (2)H32B—C32—H32C109.5
C1—C2—Cl12119.1 (2)C22—C32—H32D109.5
C1i—C3—C2119.7 (3)H32A—C32—H32D141.1
C1i—C3—Cl13119.8 (2)H32B—C32—H32D56.3
C2—C3—Cl13120.5 (2)H32C—C32—H32D56.2
N11—C11—C1178.6 (4)C22—C32—H32E109.5
C23ii—C21—C22119.7 (3)H32A—C32—H32E56.3
C23ii—C21—C31119.9 (3)H32B—C32—H32E141.1
C22—C21—C31120.4 (3)H32C—C32—H32E56.3
C23—C22—C21120.1 (3)H32D—C32—H32E109.5
C23—C22—C32120.9 (3)C22—C32—H32F109.5
C21—C22—C32118.9 (3)H32A—C32—H32F56.3
C22—C23—C21ii120.2 (3)H32B—C32—H32F56.3
C22—C23—C33120.0 (3)H32C—C32—H32F141.1
C21ii—C23—C33119.8 (3)H32D—C32—H32F109.5
C21—C31—H31A109.5H32E—C32—H32F109.5
C21—C31—H31B109.5C23—C33—H33A109.5
H31A—C31—H31B109.5C23—C33—H33B109.5
C21—C31—H31C109.5H33A—C33—H33B109.5
H31A—C31—H31C109.5C23—C33—H33C109.5
H31B—C31—H31C109.5H33A—C33—H33C109.5
C21—C31—H31D109.5H33B—C33—H33C109.5
H31A—C31—H31D141.1C23—C33—H33D109.5
H31B—C31—H31D56.3H33A—C33—H33D141.1
H31C—C31—H31D56.3H33B—C33—H33D56.3
C21—C31—H31E109.5H33C—C33—H33D56.3
H31A—C31—H31E56.3C23—C33—H33E109.5
H31B—C31—H31E141.1H33A—C33—H33E56.3
H31C—C31—H31E56.3H33B—C33—H33E141.1
H31D—C31—H31E109.5H33C—C33—H33E56.3
C21—C31—H31F109.5H33D—C33—H33E109.5
H31A—C31—H31F56.3C23—C33—H33F109.5
H31B—C31—H31F56.3H33A—C33—H33F56.3
H31C—C31—H31F141.1H33B—C33—H33F56.3
H31D—C31—H31F109.5H33C—C33—H33F141.1
H31E—C31—H31F109.5H33D—C33—H33F109.5
C22—C32—H32A109.5H33E—C33—H33F109.5
Symmetry codes: (i) x, y, z; (ii) x+1, y+2, z.
(paraII) para tetrachlorodicyanobenzene/hexamethylbenzene, 1/1, polymorph II top
Crystal data top
C8Cl4N2·C12H18Z = 1
Mr = 428.16F(000) = 220
Triclinic, P1Dx = 1.467 Mg m3
a = 7.5567 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.8956 (11) ÅCell parameters from 876 reflections
c = 8.9921 (11) Åθ = 4.5–27.5°
α = 116.697 (3)°µ = 0.62 mm1
β = 112.099 (3)°T = 174 K
γ = 92.101 (3)°Plate, yellow
V = 484.66 (11) Å30.45 × 0.25 × 0.15 mm
Data collection top
Siemens SMART arae-detector
diffractometer
2198 independent reflections
Radiation source: fine-focus sealed tube1890 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ω scansθmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan
SADABS; Sheldrick, 1996; Blessing, 1995
h = 99
Tmin = 0.80, Tmax = 0.91k = 1111
5128 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.067P)2 + 0.121P]
where P = (Fo2 + 2Fc2)/3
2198 reflections(Δ/σ)max = 0.003
122 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.31 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.0078 (2)0.1001 (2)0.1743 (2)0.0292 (3)
C20.0065 (2)0.1770 (2)0.0679 (2)0.0305 (3)
C30.0013 (2)0.0766 (2)0.1063 (2)0.0302 (3)
C70.0196 (3)0.2039 (2)0.3571 (2)0.0337 (4)
N10.0339 (2)0.2857 (2)0.5039 (2)0.0421 (4)
Cl20.01561 (7)0.39377 (5)0.15658 (6)0.04022 (16)
Cl30.00284 (7)0.16577 (6)0.24079 (6)0.03724 (15)
C110.5086 (2)0.1775 (2)0.0652 (2)0.0358 (4)
C120.4922 (2)0.0703 (3)0.1139 (2)0.0365 (4)
C130.4848 (2)0.1067 (2)0.1783 (2)0.0363 (4)
C210.5203 (3)0.3698 (3)0.1377 (3)0.0507 (5)
H21A0.49210.39460.03650.076*0.50
H21B0.65290.43730.23630.076*0.50
H21C0.42330.40170.18700.076*0.50
H21D0.55350.42780.27010.076*0.50
H21E0.39270.38510.07020.076*0.50
H21F0.62220.42070.11950.076*0.50
C220.4800 (3)0.1460 (3)0.2385 (3)0.0500 (5)
H22A0.55320.26840.16200.075*0.50
H22B0.34170.13710.31150.075*0.50
H22C0.53740.08130.32220.075*0.50
H22D0.40170.05610.36850.075*0.50
H22E0.61320.18740.21900.075*0.50
H22F0.41740.24320.20820.075*0.50
C230.4692 (3)0.2219 (3)0.3704 (3)0.0511 (5)
H23A0.41310.34310.41340.077*0.50
H23B0.60060.21020.36620.077*0.50
H23C0.38370.18690.45580.077*0.50
H23D0.51850.15040.41020.077*0.50
H23E0.33100.28320.45740.077*0.50
H23F0.54790.30660.36780.077*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0273 (7)0.0315 (8)0.0241 (7)0.0064 (6)0.0108 (6)0.0107 (6)
C20.0305 (8)0.0273 (7)0.0281 (8)0.0068 (6)0.0126 (7)0.0098 (6)
C30.0298 (8)0.0319 (8)0.0266 (8)0.0078 (6)0.0123 (6)0.0128 (6)
C70.0344 (8)0.0335 (8)0.0269 (8)0.0074 (7)0.0132 (7)0.0106 (7)
N10.0499 (9)0.0387 (8)0.0326 (8)0.0102 (7)0.0201 (7)0.0123 (7)
Cl20.0516 (3)0.0271 (2)0.0387 (3)0.01224 (18)0.0220 (2)0.01191 (18)
Cl30.0453 (3)0.0379 (2)0.0327 (2)0.01195 (18)0.01876 (19)0.01946 (19)
C110.0269 (8)0.0395 (9)0.0338 (9)0.0061 (7)0.0104 (7)0.0154 (8)
C120.0278 (8)0.0479 (10)0.0324 (9)0.0069 (7)0.0105 (7)0.0213 (8)
C130.0266 (8)0.0465 (10)0.0249 (8)0.0057 (7)0.0075 (7)0.0128 (7)
C210.0470 (11)0.0436 (11)0.0547 (12)0.0088 (9)0.0215 (10)0.0201 (10)
C220.0475 (11)0.0667 (14)0.0477 (12)0.0160 (10)0.0211 (10)0.0376 (11)
C230.0479 (11)0.0615 (13)0.0305 (9)0.0134 (10)0.0168 (9)0.0130 (9)
Geometric parameters (Å, º) top
C1—C3i1.398 (2)C21—H21C0.9800
C1—C21.402 (2)C21—H21D0.9800
C1—C71.443 (2)C21—H21E0.9800
C2—C31.387 (2)C21—H21F0.9800
C2—Cl21.7106 (16)C22—H22A0.9800
C3—C1i1.398 (2)C22—H22B0.9800
C3—Cl31.7163 (16)C22—H22C0.9800
C7—N11.144 (2)C22—H22D0.9800
C11—C13ii1.405 (3)C22—H22E0.9800
C11—C121.407 (3)C22—H22F0.9800
C11—C211.518 (3)C23—H23A0.9800
C12—C131.403 (3)C23—H23B0.9800
C12—C221.524 (3)C23—H23C0.9800
C13—C11ii1.405 (3)C23—H23D0.9800
C13—C231.515 (2)C23—H23E0.9800
C21—H21A0.9800C23—H23F0.9800
C21—H21B0.9800
C3i—C1—C2120.54 (14)C12—C22—H22B109.5
C3i—C1—C7119.38 (14)H22A—C22—H22B109.5
C2—C1—C7120.07 (15)C12—C22—H22C109.5
C3—C2—C1119.56 (15)H22A—C22—H22C109.5
C3—C2—Cl2121.35 (13)H22B—C22—H22C109.5
C1—C2—Cl2119.09 (12)C12—C22—H22D109.5
C2—C3—C1i119.90 (15)H22A—C22—H22D141.1
C2—C3—Cl3121.01 (13)H22B—C22—H22D56.3
C1i—C3—Cl3119.09 (12)H22C—C22—H22D56.3
N1—C7—C1178.19 (19)C12—C22—H22E109.5
C13ii—C11—C12119.97 (17)H22A—C22—H22E56.3
C13ii—C11—C21119.65 (16)H22B—C22—H22E141.1
C12—C11—C21120.37 (17)H22C—C22—H22E56.3
C13—C12—C11119.86 (16)H22D—C22—H22E109.5
C13—C12—C22120.09 (17)C12—C22—H22F109.5
C11—C12—C22120.05 (18)H22A—C22—H22F56.3
C12—C13—C11ii120.17 (16)H22B—C22—H22F56.3
C12—C13—C23119.94 (17)H22C—C22—H22F141.1
C11ii—C13—C23119.89 (18)H22D—C22—H22F109.5
C11—C21—H21A109.5H22E—C22—H22F109.5
C11—C21—H21B109.5C13—C23—H23A109.5
H21A—C21—H21B109.5C13—C23—H23B109.5
C11—C21—H21C109.5H23A—C23—H23B109.5
H21A—C21—H21C109.5C13—C23—H23C109.5
H21B—C21—H21C109.5H23A—C23—H23C109.5
C11—C21—H21D109.5H23B—C23—H23C109.5
H21A—C21—H21D141.1C13—C23—H23D109.5
H21B—C21—H21D56.3H23A—C23—H23D141.1
H21C—C21—H21D56.3H23B—C23—H23D56.3
C11—C21—H21E109.5H23C—C23—H23D56.3
H21A—C21—H21E56.3C13—C23—H23E109.5
H21B—C21—H21E141.1H23A—C23—H23E56.3
H21C—C21—H21E56.3H23B—C23—H23E141.1
H21D—C21—H21E109.5H23C—C23—H23E56.3
C11—C21—H21F109.5H23D—C23—H23E109.5
H21A—C21—H21F56.3C13—C23—H23F109.5
H21B—C21—H21F56.3H23A—C23—H23F56.3
H21C—C21—H21F141.1H23B—C23—H23F56.3
H21D—C21—H21F109.5H23C—C23—H23F141.1
H21E—C21—H21F109.5H23D—C23—H23F109.5
C12—C22—H22A109.5H23E—C23—H23F109.5
Symmetry codes: (i) x, y, z; (ii) x+1, y, z.
(paraIII) para tetrachlorodicyanobenzene/hexamethylbenzene, 1/1. polymorph III top
Crystal data top
C8N2Cl4·C12H18F(000) = 440
Mr = 428.16Dx = 1.404 Mg m3
Monoclinic, C2/mMo Kα radiation, λ = 0.71073 Å
a = 9.754 (2) ÅCell parameters from 799 reflections
b = 15.410 (3) Åθ = 2.6–26.9°
c = 7.5550 (15) ŵ = 0.59 mm1
β = 116.88 (3)°T = 297 K
V = 1012.9 (4) Å3Plate, yellow
Z = 20.45 × 0.25 × 0.15 mm
Data collection top
Siemens SMART area-detector
diffractometer
1204 independent reflections
Radiation source: fine-focus sealed tube876 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
SADABS; Sheldrick, 1996; Blessing, 1995
h = 1212
Tmin = 0.81, Tmax = 0.91k = 2019
5342 measured reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.09P)2 + 0.226P]
where P = (Fo2 + 2Fc2)/3
1204 reflections(Δ/σ)max = 0.001
62 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.20 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.20945 (6)0.10230 (4)0.94792 (9)0.0800 (3)
C10.50000.08984 (19)1.00000.0612 (7)
C20.3683 (2)0.04517 (14)0.9764 (3)0.0605 (5)
N10.50000.2567 (2)1.00000.0998 (11)
C70.50000.1828 (2)1.00000.0729 (8)
C120.1296 (3)0.4553 (2)0.5252 (3)0.1007 (10)
C110.00000.4112 (3)0.50000.1025 (15)
C220.2708 (6)0.4049 (5)0.5545 (6)0.244 (5)
H22A0.34540.44380.54860.366*0.50
H22B0.24330.36200.45200.366*0.50
H22C0.31340.37680.68170.366*0.50
H22D0.25600.34460.57290.366*0.50
H22E0.35810.42640.66950.366*0.50
H22F0.28800.41150.43980.366*0.50
C210.00000.3127 (4)0.50000.215 (5)
H21A0.09220.29200.50160.323*0.25
H21B0.08780.29200.61550.323*0.25
H21C0.00440.29200.38290.323*0.25
H21D0.09220.29200.49840.323*0.25
H21E0.08780.29200.38450.323*0.25
H21F0.00440.29200.61710.323*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0535 (4)0.0899 (5)0.0987 (5)0.0129 (2)0.0363 (3)0.0035 (3)
C10.0507 (14)0.0701 (18)0.0608 (16)0.0000.0235 (12)0.000
C20.0454 (9)0.0745 (12)0.0602 (11)0.0052 (8)0.0227 (8)0.0008 (9)
N10.084 (2)0.078 (2)0.147 (3)0.0000.061 (2)0.000
C70.0616 (17)0.069 (2)0.090 (2)0.0000.0359 (16)0.000
C120.0805 (16)0.159 (3)0.0569 (13)0.0436 (17)0.0262 (12)0.0148 (14)
C110.154 (5)0.087 (3)0.073 (2)0.0000.056 (3)0.000
C220.185 (5)0.444 (13)0.113 (3)0.209 (7)0.076 (4)0.077 (5)
C210.430 (17)0.090 (3)0.145 (5)0.0000.147 (8)0.000
Geometric parameters (Å, º) top
Cl1—C21.709 (2)C22—H22B0.9600
C1—C2i1.396 (2)C22—H22C0.9600
C1—C21.396 (2)C22—H22D0.9600
C1—C71.433 (5)C22—H22E0.9600
C2—C2ii1.392 (4)C22—H22F0.9600
N1—C71.139 (4)C21—H21A0.9600
C12—C111.370 (4)C21—H21B0.9600
C12—C12iii1.378 (8)C21—H21C0.9600
C12—C221.507 (5)C21—H21D0.9600
C11—C12iv1.370 (4)C21—H21E0.9600
C11—C211.518 (7)C21—H21F0.9600
C22—H22A0.9600
C2i—C1—C2120.9 (3)C12—C22—H22F109.5
C2i—C1—C7119.55 (13)H22A—C22—H22F56.3
C2—C1—C7119.55 (13)H22B—C22—H22F56.3
C2ii—C2—C1119.55 (13)H22C—C22—H22F141.1
C2ii—C2—Cl1121.01 (8)H22D—C22—H22F109.5
C1—C2—Cl1119.45 (17)H22E—C22—H22F109.5
N1—C7—C1180.000 (1)C11—C21—H21A109.5
C11—C12—C12iii119.7 (2)C11—C21—H21B109.5
C11—C12—C22119.3 (4)H21A—C21—H21B109.5
C12iii—C12—C22121.0 (3)C11—C21—H21C109.5
C12—C11—C12iv120.6 (4)H21A—C21—H21C109.5
C12—C11—C21119.7 (2)H21B—C21—H21C109.5
C12iv—C11—C21119.7 (2)C11—C21—H21D109.5
C12—C22—H22A109.5H21A—C21—H21D141.1
C12—C22—H22B109.5H21B—C21—H21D56.3
H22A—C22—H22B109.5H21C—C21—H21D56.3
C12—C22—H22C109.5C11—C21—H21E109.5
H22A—C22—H22C109.5H21A—C21—H21E56.3
H22B—C22—H22C109.5H21B—C21—H21E141.1
C12—C22—H22D109.5H21C—C21—H21E56.3
H22A—C22—H22D141.1H21D—C21—H21E109.5
H22B—C22—H22D56.3C11—C21—H21F109.5
H22C—C22—H22D56.3H21A—C21—H21F56.3
C12—C22—H22E109.5H21B—C21—H21F56.3
H22A—C22—H22E56.3H21C—C21—H21F141.1
H22B—C22—H22E141.1H21D—C21—H21F109.5
H22C—C22—H22E56.3H21E—C21—H21F109.5
H22D—C22—H22E109.5
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 top
Crystal data top
C8N2Cl4·C12H18Z = 2
Mr = 428.16F(000) = 440
Triclinic, P1Dx = 1.451 Mg m3
a = 7.4982 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.0371 (3) ÅCell parameters from 1500 reflections
c = 15.4538 (6) Åθ = 2–25°
α = 85.080 (2)°µ = 0.61 mm1
β = 81.795 (2)°T = 174 K
γ = 71.168 (2)°Deformed needle, yellow
V = 980.10 (5) Å30.30 × 0.26 × 0.18 mm
Data collection top
SMART
diffractometer
3354 independent reflections
Radiation source: fine-focus sealed tube1520 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
ω scansθmax = 25.1°, θmin = 1.3°
Absorption correction: multi-scan
SADABS; Sheldrick, 1996; Blessing, 1995
h = 88
Tmin = 0.79, Tmax = 0.90k = 1010
5453 measured reflectionsl = 1816
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.094Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.247H atoms treated by a mixture of independent and constrained refinement
S = 0.90 w = 1/[σ2(Fo2) + (0.137P)2]
where P = (Fo2 + 2Fc2)/3
3354 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.71 e Å3
0 restraintsΔρmin = 0.97 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C11.0407 (9)0.6233 (8)0.0488 (5)0.0306 (18)
C20.9681 (10)0.6406 (7)0.0375 (5)0.0314 (18)
C30.9266 (9)0.5220 (8)0.0898 (5)0.0319 (19)
C111.0761 (10)0.7550 (9)0.0994 (5)0.0297 (18)
N111.1039 (9)0.8562 (7)0.1402 (5)0.0491 (19)
Cl120.9253 (3)0.8184 (2)0.08411 (14)0.0437 (6)
Cl130.8361 (3)0.5374 (2)0.19632 (13)0.0433 (6)
C210.5418 (9)0.8655 (7)0.4557 (5)0.0261 (17)
C220.5683 (10)0.9989 (8)0.4109 (5)0.035 (2)
C230.5241 (10)1.1351 (8)0.4573 (5)0.0333 (19)
C310.5863 (10)0.7157 (8)0.4116 (4)0.0287 (18)
N310.6202 (10)0.6150 (7)0.3714 (5)0.057 (2)
Cl320.6542 (3)0.9935 (2)0.30215 (13)0.0449 (6)
Cl330.5525 (3)1.3027 (2)0.40495 (14)0.0474 (7)
C410.5320 (11)0.6285 (8)0.0468 (6)0.038 (2)
C420.4608 (10)0.6404 (8)0.0413 (6)0.038 (2)
C430.4314 (10)0.5115 (9)0.0887 (5)0.037 (2)
C510.5684 (12)0.7696 (9)0.0981 (6)0.056 (3)
H51A0.62810.73980.15730.085*0.50
H51B0.65270.80630.06860.085*0.50
H51C0.44760.85360.10120.085*0.50
H51D0.52420.86000.06080.085*0.50
H51E0.49960.79350.14950.085*0.50
H51F0.70470.74620.11690.085*0.50
C520.4179 (13)0.7942 (9)0.0852 (6)0.062 (3)
H52A0.48220.77570.13800.092*0.50
H52B0.28060.83860.10140.092*0.50
H52C0.46340.86750.04470.092*0.50
H52D0.33530.87890.05140.092*0.50
H52E0.53680.81590.08800.092*0.50
H52F0.35410.78700.14460.092*0.50
C530.3597 (12)0.5188 (11)0.1862 (5)0.063 (3)
H53A0.34820.41700.20840.094*0.50
H53B0.23530.59930.19530.094*0.50
H53C0.44960.54490.21760.094*0.50
H53D0.34060.62380.20580.094*0.50
H53E0.45340.44150.21890.094*0.50
H53F0.23910.49590.19660.094*0.50
C610.0401 (10)0.8498 (8)0.4726 (6)0.039 (2)
C620.0731 (10)0.9639 (9)0.4135 (5)0.039 (2)
C630.0352 (10)1.1162 (8)0.4398 (5)0.038 (2)
C710.0821 (13)0.6845 (9)0.4417 (7)0.072 (3)
H71A0.03480.62110.48830.108*0.50
H71B0.21940.63700.42710.108*0.50
H71C0.01890.68940.38970.108*0.50
H71D0.14730.67720.38180.108*0.50
H71E0.03730.66140.44290.108*0.50
H71F0.16320.60890.48040.108*0.50
C720.1551 (12)0.9285 (11)0.3178 (6)0.067 (3)
H72A0.13971.02690.28320.100*0.50
H72B0.08760.86740.29420.100*0.50
H72C0.29030.86840.31500.100*0.50
H72D0.20540.81490.31170.100*0.50
H72E0.25740.97440.30070.100*0.50
H72F0.05480.97340.28000.100*0.50
C730.0677 (11)1.2424 (10)0.3763 (6)0.058 (3)
H73A0.01651.34340.40410.087*0.50
H73B0.00381.24610.32470.087*0.50
H73C0.20431.22010.35840.087*0.50
H73D0.13321.19640.32070.087*0.50
H73E0.14591.29360.40020.087*0.50
H73F0.05461.31970.36640.087*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.019 (4)0.034 (4)0.039 (5)0.007 (3)0.004 (3)0.001 (4)
C20.024 (4)0.026 (4)0.051 (5)0.014 (3)0.012 (4)0.003 (4)
C30.019 (4)0.027 (4)0.052 (5)0.005 (3)0.017 (4)0.000 (4)
C110.021 (4)0.039 (5)0.031 (4)0.013 (4)0.007 (3)0.010 (4)
N110.048 (5)0.043 (4)0.065 (5)0.023 (4)0.020 (4)0.008 (4)
Cl120.0471 (14)0.0318 (11)0.0579 (14)0.0185 (9)0.0097 (10)0.0025 (9)
Cl130.0456 (13)0.0465 (13)0.0426 (12)0.0220 (10)0.0043 (10)0.0005 (10)
C210.025 (4)0.021 (4)0.036 (5)0.011 (3)0.008 (3)0.000 (3)
C220.022 (5)0.037 (4)0.050 (5)0.011 (4)0.005 (4)0.012 (4)
C230.027 (4)0.023 (4)0.053 (5)0.012 (3)0.008 (4)0.004 (4)
C310.031 (5)0.029 (4)0.024 (4)0.007 (4)0.002 (3)0.008 (4)
N310.065 (6)0.031 (4)0.074 (6)0.017 (4)0.010 (4)0.009 (4)
Cl320.0539 (14)0.0463 (12)0.0382 (12)0.0230 (10)0.0013 (10)0.0005 (9)
Cl330.0541 (14)0.0305 (11)0.0654 (15)0.0230 (10)0.0160 (11)0.0086 (10)
C410.035 (5)0.026 (4)0.059 (6)0.014 (4)0.017 (4)0.008 (4)
C420.030 (5)0.028 (4)0.060 (6)0.013 (4)0.011 (4)0.002 (4)
C430.033 (5)0.046 (5)0.040 (5)0.018 (4)0.014 (4)0.001 (4)
C510.045 (6)0.043 (5)0.089 (7)0.024 (4)0.026 (5)0.024 (5)
C520.067 (7)0.034 (5)0.088 (7)0.013 (5)0.022 (6)0.018 (5)
C530.059 (6)0.083 (7)0.060 (6)0.038 (5)0.018 (5)0.008 (5)
C610.032 (5)0.025 (4)0.067 (6)0.013 (4)0.024 (4)0.001 (4)
C620.031 (5)0.035 (4)0.045 (5)0.002 (4)0.015 (4)0.008 (4)
C630.032 (5)0.032 (4)0.051 (6)0.011 (4)0.018 (4)0.017 (4)
C710.075 (8)0.041 (5)0.099 (8)0.009 (5)0.023 (6)0.021 (5)
C720.053 (6)0.072 (7)0.068 (7)0.005 (5)0.019 (5)0.000 (5)
C730.033 (5)0.065 (6)0.080 (7)0.025 (5)0.013 (5)0.023 (5)
Geometric parameters (Å, º) top
C1—C21.368 (10)C52—H52E0.9800
C1—C3i1.441 (10)C52—H52F0.9800
C1—C111.444 (9)C53—H53A0.9800
C2—C31.377 (9)C53—H53B0.9800
C2—Cl121.733 (7)C53—H53C0.9800
C3—C1i1.441 (10)C53—H53D0.9800
C3—Cl131.688 (8)C53—H53E0.9800
C11—N111.125 (8)C53—H53F0.9800
C21—C23ii1.364 (10)C61—C621.378 (10)
C21—C221.394 (9)C61—C63iv1.409 (10)
C21—C311.487 (9)C61—C711.529 (10)
C22—C231.399 (9)C62—C631.397 (10)
C22—Cl321.711 (8)C62—C721.536 (11)
C23—C21ii1.364 (10)C63—C61iv1.409 (10)
C23—Cl331.716 (7)C63—C731.497 (10)
C31—N311.087 (9)C71—H71A0.9800
C41—C421.389 (11)C71—H71B0.9800
C41—C43iii1.401 (10)C71—H71C0.9800
C41—C511.522 (10)C71—H71D0.9800
C42—C431.384 (10)C71—H71E0.9800
C42—C521.519 (10)C71—H71F0.9800
C43—C41iii1.401 (10)C72—H72A0.9800
C43—C531.525 (11)C72—H72B0.9800
C51—H51A0.9800C72—H72C0.9800
C51—H51B0.9800C72—H72D0.9800
C51—H51C0.9800C72—H72E0.9800
C51—H51D0.9800C72—H72F0.9800
C51—H51E0.9800C73—H73A0.9800
C51—H51F0.9800C73—H73B0.9800
C52—H52A0.9800C73—H73C0.9800
C52—H52B0.9800C73—H73D0.9800
C52—H52C0.9800C73—H73E0.9800
C52—H52D0.9800C73—H73F0.9800
C2—C1—C3i120.6 (7)H53A—C53—H53E56.3
C2—C1—C11119.0 (7)H53B—C53—H53E141.1
C3i—C1—C11120.3 (7)H53C—C53—H53E56.3
C1—C2—C3122.7 (6)H53D—C53—H53E109.5
C1—C2—Cl12119.5 (6)C43—C53—H53F109.5
C3—C2—Cl12117.8 (6)H53A—C53—H53F56.3
C2—C3—C1i116.6 (7)H53B—C53—H53F56.3
C2—C3—Cl13124.6 (6)H53C—C53—H53F141.1
C1i—C3—Cl13118.7 (6)H53D—C53—H53F109.5
N11—C11—C1178.7 (8)H53E—C53—H53F109.5
C23ii—C21—C22121.8 (6)C62—C61—C63iv121.3 (7)
C23ii—C21—C31116.4 (6)C62—C61—C71119.0 (8)
C22—C21—C31121.8 (6)C63iv—C61—C71119.7 (7)
C21—C22—C23118.3 (7)C61—C62—C63120.3 (7)
C21—C22—Cl32120.2 (5)C61—C62—C72121.8 (7)
C23—C22—Cl32121.5 (6)C63—C62—C72117.9 (7)
C21ii—C23—C22119.9 (6)C62—C63—C61iv118.4 (7)
C21ii—C23—Cl33120.0 (6)C62—C63—C73121.2 (8)
C22—C23—Cl33120.1 (6)C61iv—C63—C73120.4 (7)
N31—C31—C21172.5 (8)C61—C71—H71A109.5
C42—C41—C43iii120.5 (7)C61—C71—H71B109.5
C42—C41—C51119.5 (7)H71A—C71—H71B109.5
C43iii—C41—C51120.0 (8)C61—C71—H71C109.5
C43—C42—C41119.8 (7)H71A—C71—H71C109.5
C43—C42—C52120.4 (8)H71B—C71—H71C109.5
C41—C42—C52119.8 (7)C61—C71—H71D109.5
C42—C43—C41iii119.7 (7)H71A—C71—H71D141.1
C42—C43—C53121.2 (7)H71B—C71—H71D56.3
C41iii—C43—C53119.1 (7)H71C—C71—H71D56.3
C41—C51—H51A109.5C61—C71—H71E109.5
C41—C51—H51B109.5H71A—C71—H71E56.3
H51A—C51—H51B109.5H71B—C71—H71E141.1
C41—C51—H51C109.5H71C—C71—H71E56.3
H51A—C51—H51C109.5H71D—C71—H71E109.5
H51B—C51—H51C109.5C61—C71—H71F109.5
C41—C51—H51D109.5H71A—C71—H71F56.3
H51A—C51—H51D141.1H71B—C71—H71F56.3
H51B—C51—H51D56.3H71C—C71—H71F141.1
H51C—C51—H51D56.3H71D—C71—H71F109.5
C41—C51—H51E109.5H71E—C71—H71F109.5
H51A—C51—H51E56.3C62—C72—H72A109.5
H51B—C51—H51E141.1C62—C72—H72B109.5
H51C—C51—H51E56.3H72A—C72—H72B109.5
H51D—C51—H51E109.5C62—C72—H72C109.5
C41—C51—H51F109.5H72A—C72—H72C109.5
H51A—C51—H51F56.3H72B—C72—H72C109.5
H51B—C51—H51F56.3C62—C72—H72D109.5
H51C—C51—H51F141.1H72A—C72—H72D141.1
H51D—C51—H51F109.5H72B—C72—H72D56.3
H51E—C51—H51F109.5H72C—C72—H72D56.3
C42—C52—H52A109.5C62—C72—H72E109.5
C42—C52—H52B109.5H72A—C72—H72E56.3
H52A—C52—H52B109.5H72B—C72—H72E141.1
C42—C52—H52C109.5H72C—C72—H72E56.3
H52A—C52—H52C109.5H72D—C72—H72E109.5
H52B—C52—H52C109.5C62—C72—H72F109.5
C42—C52—H52D109.5H72A—C72—H72F56.3
H52A—C52—H52D141.1H72B—C72—H72F56.3
H52B—C52—H52D56.3H72C—C72—H72F141.1
H52C—C52—H52D56.3H72D—C72—H72F109.5
C42—C52—H52E109.5H72E—C72—H72F109.5
H52A—C52—H52E56.3C63—C73—H73A109.5
H52B—C52—H52E141.1C63—C73—H73B109.5
H52C—C52—H52E56.3H73A—C73—H73B109.5
H52D—C52—H52E109.5C63—C73—H73C109.5
C42—C52—H52F109.5H73A—C73—H73C109.5
H52A—C52—H52F56.3H73B—C73—H73C109.5
H52B—C52—H52F56.3C63—C73—H73D109.5
H52C—C52—H52F141.1H73A—C73—H73D141.1
H52D—C52—H52F109.5H73B—C73—H73D56.3
H52E—C52—H52F109.5H73C—C73—H73D56.3
C43—C53—H53A109.5C63—C73—H73E109.5
C43—C53—H53B109.5H73A—C73—H73E56.3
H53A—C53—H53B109.5H73B—C73—H73E141.1
C43—C53—H53C109.5H73C—C73—H73E56.3
H53A—C53—H53C109.5H73D—C73—H73E109.5
H53B—C53—H53C109.5C63—C73—H73F109.5
C43—C53—H53D109.5H73A—C73—H73F56.3
H53A—C53—H53D141.1H73B—C73—H73F56.3
H53B—C53—H53D56.3H73C—C73—H73F141.1
H53C—C53—H53D56.3H73D—C73—H73F109.5
C43—C53—H53E109.5H73E—C73—H73F109.5
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.
 

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