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Acta Cryst. (2017). B73, 163-167
https://doi.org/10.1107/S2052520616016450
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A new tecton with parallel halogen-bond donors: a path to supramolecular rectangles

T. K. Wijethunga, M. Đaković, J. Desper and C. B. Aakeröy
A new tecton, 1,8-diiodoethynylanthracene, with two halogen-bond donor sites was synthesized and characterized. This tecton is capable of forming two parallel halogen bonds at once, which makes it a useful building block for the construction of a variety of supramolecular squares and rectangles.
Keywords: halogen bonding; co-crystal; tecton; supramolecular chemistry.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520616016450/ao5017sup1.cif
Contains datablocks DIEABipy, DIEAAzopy, DIEABipyNO, DIEABpe, DIEABpen

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616016450/ao5017DIEABipysup2.hkl
Contains datablock DIEABipy

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616016450/ao5017DIEAAzopysup3.hkl
Contains datablock DIEAAzopy

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616016450/ao5017DIEABipyNOsup4.hkl
Contains datablock DIEABipyNO

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616016450/ao5017DIEABpesup5.hkl
Contains datablock DIEABpe

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616016450/ao5017DIEABpensup6.hkl
Contains datablock DIEABpen

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520616016450/ao5017sup7.pdf
Comprehensive synthetic procedures and characterizations

CCDC references: 1483700; 1483701; 1483702; 1483703; 1483704

Computing details top

Data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.37.35 for DIEABipy, DIEAAzopy; Bruker APEX2 for DIEABipyNO, DIEABpe, DIEABpen. Cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.37.35 for DIEABipy, DIEAAzopy; Bruker SAINT for DIEABipyNO, DIEABpe, DIEABpen. Data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.37.35 for DIEABipy, DIEAAzopy; Bruker SAINT for DIEABipyNO, DIEABpe, DIEABpen. Program(s) used to solve structure: SHELXS2013 (Sheldrick, 2013) for DIEABipy, DIEAAzopy; SHELXS97 (Sheldrick 2008) for DIEABipyNO, DIEABpe, DIEABpen. Program(s) used to refine structure: SHELXS2013 (Sheldrick, 2013) for DIEABipy, DIEAAzopy; SHELXL2013 (Sheldrick, 2013) for DIEABipyNO, DIEABpe, DIEABpen. Molecular graphics: Mercury (Bruno et al., 2002) for DIEABipy, DIEAAzopy; Bruker SHELXTL for DIEABipyNO, DIEABpe, DIEABpen. Software used to prepare material for publication: SHELXL2013 (Sheldrick, 2013) and PLATON (Spek, 2003) for DIEABipy, DIEAAzopy; Bruker SHELXTL for DIEABipyNO, DIEABpe, DIEABpen.

(DIEABipy) top
Crystal data top
C18H8I2·2(C10H8N2)V = 1601.35 (12) Å3
Mr = 790.45Z = 2
Triclinic, P1F(000) = 772
a = 9.7245 (4) ÅDx = 1.639 Mg m−3
b = 10.1191 (4) ÅMo Kα radiation, λ = 0.71073 Å
c = 17.5288 (7) ŵ = 2.00 mm−1
α = 87.839 (3)°T = 296 K
β = 80.433 (4)°Block, yellow
γ = 70.331 (4)°0.49 × 0.29 × 0.23 mm
Data collection top
Oxford Diffraction Xcalibur diffractometet with Saphire3 detector9306 independent reflections
Radiation source: Enhance (Mo)X-ray Source6617 reflections with i > 2σ(i)
Graphite monochromatorRint = 0.023
ω scansθmax = 30.0°, θmin = 4.2°
Absorption correction: multi-scan
SADABS		h = −13→13
Tmin = 0.497, Tmax = 0.629k = −14→14
16639 measured reflectionsl = −24→22
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-atom parameters constrained
S = 1.00 W = 1/[Σ2(FO2) + (0.0294P)2] WHERE P = (FO2 + 2FC2)/3
9306 reflections(Δ/σ)max = 0.001
397 parametersΔρmax = 0.58 e Å−3
0 restraintsΔρmin = −0.61 e Å−3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.34436 (2)0.26571 (2)0.49644 (2)0.05450 (10)
I20.15213 (2)0.65666 (2)0.37374 (2)0.05360 (10)
C10.3940 (3)−0.0154 (3)0.28349 (18)0.0465 (10)
C20.3559 (3)0.0572 (3)0.21365 (16)0.0412 (8)
C30.3039 (3)0.2032 (3)0.21089 (15)0.0396 (8)
C40.2652 (3)0.2725 (3)0.14387 (15)0.0399 (8)
C50.2093 (3)0.4249 (3)0.14120 (16)0.0456 (9)
C60.1734 (4)0.4879 (3)0.07338 (19)0.0609 (11)
C70.1894 (4)0.4082 (4)0.00608 (19)0.0662 (11)
C80.2397 (3)0.2664 (4)0.00682 (18)0.0586 (11)
C90.2797 (3)0.1929 (3)0.07526 (16)0.0445 (9)
C100.3312 (3)0.0469 (3)0.07840 (17)0.0504 (10)
C110.3701 (3)−0.0231 (3)0.14535 (17)0.0449 (9)
C120.4180 (3)−0.1720 (3)0.1491 (2)0.0592 (11)
C130.4506 (4)−0.2369 (3)0.2155 (2)0.0650 (13)
C140.4403 (3)−0.1595 (3)0.2835 (2)0.0596 (11)
C150.3833 (3)0.0641 (3)0.35117 (18)0.0488 (10)
C160.3726 (3)0.1369 (3)0.40589 (18)0.0534 (11)
C170.1928 (3)0.5032 (3)0.21048 (18)0.0480 (9)
C180.1805 (3)0.5603 (3)0.27019 (19)0.0532 (10)
N10.6980 (3)0.5555 (3)0.37764 (16)0.0642 (10)
N20.7543 (4)0.2073 (4)0.02593 (18)0.0822 (14)
C190.7968 (4)0.5588 (4)0.3162 (2)0.0687 (12)
C200.8159 (3)0.4875 (3)0.2477 (2)0.0611 (11)
C210.7257 (3)0.4092 (3)0.24036 (17)0.0450 (9)
C220.6225 (3)0.4058 (3)0.30497 (18)0.0536 (10)
C230.6138 (4)0.4785 (3)0.37111 (19)0.0625 (12)
C240.7366 (3)0.3373 (3)0.16730 (17)0.0470 (9)
C250.8711 (3)0.2668 (3)0.12202 (18)0.0555 (11)
C260.8739 (4)0.2036 (4)0.0534 (2)0.0677 (12)
C270.6254 (4)0.2776 (5)0.0691 (2)0.0927 (18)
C280.6104 (4)0.3423 (4)0.1387 (2)0.0728 (14)
N30.8800 (3)1.2073 (3)0.48766 (17)0.0644 (10)
N40.9040 (3)0.8622 (3)0.13937 (18)0.0767 (11)
C290.9659 (4)1.2191 (4)0.4232 (2)0.0647 (11)
C300.9767 (3)1.1530 (3)0.35416 (19)0.0561 (11)
C310.8908 (3)1.0687 (3)0.35069 (16)0.0428 (8)
C320.7986 (4)1.0580 (3)0.41798 (18)0.0622 (11)
C330.7985 (4)1.1267 (4)0.48464 (19)0.0701 (14)
C340.8947 (3)0.9976 (3)0.27823 (16)0.0444 (9)
C351.0237 (3)0.9456 (3)0.22497 (17)0.0508 (10)
C361.0223 (4)0.8806 (3)0.15847 (19)0.0630 (11)
C370.7820 (4)0.9129 (5)0.1899 (2)0.0965 (18)
C380.7698 (4)0.9807 (4)0.2590 (2)0.0764 (14)
H30.294900.255400.255100.0470*
H60.137700.585400.071600.0730*
H70.164900.45380−0.039300.0790*
H80.248500.21590−0.038000.0700*
H100.33980−0.005200.034200.0600*
H120.42690−0.225100.105200.0710*
H130.48060−0.334300.217000.0780*
H140.46500−0.206800.328500.0720*
H200.517000.388900.166300.0880*
H210.539400.283100.050700.1120*
H220.965600.155300.024600.0810*
H230.959100.262200.137900.0670*
H250.559700.354400.303400.0640*
H260.545000.473400.413800.0750*
H270.856800.612400.319500.0820*
H280.888500.491800.206800.0730*
H300.679301.014100.291700.0920*
H310.696400.902300.178200.1160*
H321.110800.846800.124200.0760*
H331.111200.955000.234600.0610*
H350.737001.004800.418400.0750*
H360.738001.115700.529700.0840*
H371.023301.276100.424400.0780*
H381.040301.164600.310600.0670*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.06240 (10)0.06570 (10)0.04010 (10)−0.02660 (10)−0.00920 (10)−0.00510 (10)
I20.05810 (10)0.05640 (10)0.04410 (10)−0.01390 (10)−0.00990 (10)−0.01430 (10)
C10.0373 (14)0.0525 (16)0.0507 (19)−0.0189 (12)0.0010 (12)−0.0101 (13)
C20.0343 (13)0.0515 (15)0.0415 (16)−0.0209 (11)−0.0002 (11)−0.0113 (12)
C30.0384 (13)0.0506 (14)0.0336 (14)−0.0214 (11)0.0007 (10)−0.0138 (11)
C40.0356 (13)0.0543 (15)0.0333 (15)−0.0214 (11)0.0017 (10)−0.0136 (11)
C50.0450 (15)0.0561 (16)0.0374 (16)−0.0203 (12)−0.0016 (12)−0.0112 (12)
C60.071 (2)0.0621 (18)0.049 (2)−0.0206 (16)−0.0103 (16)−0.0048 (15)
C70.079 (2)0.081 (2)0.0399 (19)−0.0252 (18)−0.0163 (16)0.0010 (16)
C80.0595 (19)0.084 (2)0.0372 (18)−0.0309 (17)−0.0031 (14)−0.0167 (15)
C90.0399 (14)0.0627 (17)0.0343 (15)−0.0226 (12)−0.0006 (11)−0.0153 (12)
C100.0477 (16)0.0677 (18)0.0394 (17)−0.0269 (14)0.0051 (12)−0.0269 (13)
C110.0360 (14)0.0527 (15)0.0480 (18)−0.0197 (11)0.0024 (12)−0.0190 (12)
C120.0522 (18)0.0578 (18)0.067 (2)−0.0192 (14)−0.0002 (16)−0.0272 (16)
C130.059 (2)0.0457 (16)0.087 (3)−0.0135 (14)−0.0071 (18)−0.0163 (17)
C140.0569 (19)0.0562 (18)0.065 (2)−0.0180 (14)−0.0090 (16)−0.0031 (15)
C150.0410 (15)0.0584 (17)0.0470 (18)−0.0167 (12)−0.0068 (13)−0.0009 (14)
C160.0567 (18)0.0601 (18)0.0454 (19)−0.0201 (14)−0.0127 (14)0.0007 (14)
C170.0510 (16)0.0476 (15)0.0465 (18)−0.0174 (12)−0.0070 (13)−0.0073 (12)
C180.0563 (17)0.0502 (16)0.052 (2)−0.0154 (13)−0.0077 (14)−0.0139 (13)
N10.0658 (17)0.0781 (18)0.0507 (18)−0.0250 (14)−0.0088 (14)−0.0188 (13)
N20.078 (2)0.122 (3)0.060 (2)−0.0571 (19)0.0117 (16)−0.0418 (18)
C190.062 (2)0.093 (2)0.063 (2)−0.0409 (18)−0.0055 (17)−0.0245 (18)
C200.0485 (17)0.083 (2)0.059 (2)−0.0336 (16)0.0004 (15)−0.0183 (17)
C210.0418 (15)0.0515 (15)0.0405 (16)−0.0137 (12)−0.0059 (12)−0.0065 (12)
C220.0569 (18)0.0596 (17)0.0496 (19)−0.0289 (14)−0.0013 (14)−0.0076 (14)
C230.069 (2)0.074 (2)0.046 (2)−0.0301 (17)0.0021 (15)−0.0107 (15)
C240.0450 (15)0.0527 (15)0.0464 (18)−0.0236 (13)0.0012 (12)−0.0069 (13)
C250.0483 (17)0.0686 (19)0.049 (2)−0.0197 (14)−0.0034 (14)−0.0116 (15)
C260.063 (2)0.081 (2)0.056 (2)−0.0272 (17)0.0108 (16)−0.0251 (17)
C270.070 (2)0.158 (4)0.068 (3)−0.064 (3)0.005 (2)−0.048 (3)
C280.0533 (19)0.114 (3)0.059 (2)−0.0415 (19)0.0055 (16)−0.035 (2)
N30.0656 (17)0.0769 (18)0.0484 (18)−0.0183 (14)−0.0100 (14)−0.0206 (13)
N40.0678 (19)0.111 (2)0.059 (2)−0.0413 (17)0.0009 (15)−0.0378 (17)
C290.0571 (19)0.084 (2)0.060 (2)−0.0320 (17)−0.0057 (16)−0.0243 (17)
C300.0440 (16)0.079 (2)0.0476 (19)−0.0251 (15)−0.0001 (13)−0.0164 (15)
C310.0417 (14)0.0508 (15)0.0352 (15)−0.0135 (11)−0.0068 (11)−0.0061 (11)
C320.078 (2)0.074 (2)0.0422 (19)−0.0422 (18)0.0070 (16)−0.0095 (15)
C330.089 (3)0.087 (2)0.0349 (19)−0.037 (2)0.0069 (17)−0.0128 (16)
C340.0464 (15)0.0531 (15)0.0358 (15)−0.0198 (12)−0.0045 (12)−0.0069 (12)
C350.0407 (15)0.0678 (18)0.0428 (17)−0.0173 (13)−0.0025 (12)−0.0144 (13)
C360.0545 (19)0.083 (2)0.048 (2)−0.0212 (16)0.0032 (15)−0.0251 (16)
C370.063 (2)0.166 (4)0.077 (3)−0.061 (3)0.005 (2)−0.059 (3)
C380.0518 (19)0.127 (3)0.061 (2)−0.048 (2)0.0096 (16)−0.042 (2)
Geometric parameters (Å, º) top
I1—C162.016 (3)C12—H120.9300
I1—N1i2.795 (3)C13—H130.9300
I2—C182.027 (3)C14—H140.9300
I2—N3ii2.758 (3)C19—C201.378 (5)
N1—C231.326 (5)C20—C211.388 (4)
N1—C191.326 (5)C21—C221.391 (4)
N2—C261.320 (6)C21—C241.468 (4)
N2—C271.332 (6)C22—C231.372 (4)
N3—C291.316 (5)C24—C281.386 (5)
N3—C331.322 (5)C24—C251.385 (4)
N4—C361.322 (5)C25—C261.376 (5)
N4—C371.316 (5)C27—C281.369 (5)
C1—C151.428 (4)C19—H270.9300
C1—C141.374 (4)C20—H280.9300
C1—C21.441 (4)C22—H250.9300
C2—C31.393 (4)C23—H260.9300
C2—C111.434 (4)C25—H230.9300
C3—C41.386 (4)C26—H220.9300
C4—C51.454 (4)C27—H210.9300
C4—C91.434 (4)C28—H200.9300
C5—C171.432 (4)C29—C301.376 (5)
C5—C61.368 (4)C30—C311.389 (4)
C6—C71.412 (5)C31—C321.382 (4)
C7—C81.352 (5)C31—C341.472 (4)
C8—C91.427 (4)C32—C331.382 (5)
C9—C101.393 (4)C34—C351.388 (4)
C10—C111.388 (4)C34—C381.378 (5)
C11—C121.422 (4)C35—C361.364 (4)
C12—C131.346 (5)C37—C381.383 (5)
C13—C141.422 (5)C29—H370.9300
C15—C161.201 (4)C30—H380.9300
C17—C181.184 (4)C32—H350.9300
C3—H30.9300C33—H360.9300
C6—H60.9300C35—H330.9300
C7—H70.9300C36—H320.9300
C8—H80.9300C37—H310.9300
C10—H100.9300C38—H300.9300
C16—I1—N1i179.38 (10)C20—C21—C22116.5 (3)
C18—I2—N3ii178.00 (10)C21—C22—C23119.7 (3)
C19—N1—C23116.7 (3)N1—C23—C22123.8 (3)
C26—N2—C27115.9 (3)C21—C24—C25122.5 (3)
C29—N3—C33116.8 (3)C25—C24—C28116.7 (3)
C36—N4—C37114.9 (3)C21—C24—C28120.8 (3)
C2—C1—C15119.2 (3)C24—C25—C26119.7 (3)
C2—C1—C14119.3 (3)N2—C26—C25124.0 (4)
C14—C1—C15121.4 (3)N2—C27—C28124.7 (4)
C1—C2—C11119.1 (3)C24—C28—C27119.0 (4)
C3—C2—C11119.1 (3)N1—C19—H27118.00
C1—C2—C3121.9 (3)C20—C19—H27118.00
C2—C3—C4121.6 (3)C19—C20—H28120.00
C3—C4—C5121.6 (2)C21—C20—H28120.00
C3—C4—C9119.6 (3)C23—C22—H25120.00
C5—C4—C9118.8 (2)C21—C22—H25120.00
C4—C5—C17118.2 (2)N1—C23—H26118.00
C6—C5—C17122.6 (3)C22—C23—H26118.00
C4—C5—C6119.2 (3)C24—C25—H23120.00
C5—C6—C7121.4 (3)C26—C25—H23120.00
C6—C7—C8120.8 (3)C25—C26—H22118.00
C7—C8—C9121.1 (3)N2—C26—H22118.00
C8—C9—C10122.8 (3)N2—C27—H21118.00
C4—C9—C8118.7 (3)C28—C27—H21118.00
C4—C9—C10118.6 (3)C27—C28—H20120.00
C9—C10—C11122.1 (3)C24—C28—H20121.00
C2—C11—C12119.0 (3)N3—C29—C30124.5 (4)
C10—C11—C12122.0 (3)C29—C30—C31118.8 (3)
C2—C11—C10119.0 (3)C30—C31—C32116.8 (3)
C11—C12—C13120.7 (3)C30—C31—C34121.5 (3)
C12—C13—C14121.3 (3)C32—C31—C34121.7 (3)
C1—C14—C13120.6 (3)C31—C32—C33119.7 (3)
C1—C15—C16176.7 (3)N3—C33—C32123.4 (3)
I1—C16—C15177.0 (3)C31—C34—C35122.0 (3)
C5—C17—C18175.9 (3)C31—C34—C38121.8 (3)
I2—C18—C17177.8 (3)C35—C34—C38116.2 (3)
C2—C3—H3119.00C34—C35—C36120.0 (3)
C4—C3—H3119.00N4—C36—C35124.6 (3)
C7—C6—H6119.00N4—C37—C38125.7 (4)
C5—C6—H6119.00C34—C38—C37118.5 (3)
C6—C7—H7120.00N3—C29—H37118.00
C8—C7—H7120.00C30—C29—H37118.00
C9—C8—H8119.00C29—C30—H38121.00
C7—C8—H8119.00C31—C30—H38121.00
C9—C10—H10119.00C31—C32—H35120.00
C11—C10—H10119.00C33—C32—H35120.00
C11—C12—H12120.00N3—C33—H36118.00
C13—C12—H12120.00C32—C33—H36118.00
C14—C13—H13119.00C34—C35—H33120.00
C12—C13—H13119.00C36—C35—H33120.00
C1—C14—H14120.00N4—C36—H32118.00
C13—C14—H14120.00C35—C36—H32118.00
N1—C19—C20123.9 (4)N4—C37—H31117.00
C19—C20—C21119.4 (3)C38—C37—H31117.00
C20—C21—C24121.4 (3)C34—C38—H30121.00
C22—C21—C24122.1 (3)C37—C38—H30121.00
C19—N1—C23—C22−1.1 (5)C9—C10—C11—C12177.9 (3)
C23—N1—C19—C20−0.2 (5)C9—C10—C11—C20.5 (5)
C26—N2—C27—C28−1.0 (6)C10—C11—C12—C13−177.9 (3)
C27—N2—C26—C250.0 (6)C2—C11—C12—C13−0.5 (5)
C29—N3—C33—C32−0.9 (5)C11—C12—C13—C14−0.9 (5)
C33—N3—C29—C30−0.5 (6)C12—C13—C14—C11.2 (5)
C36—N4—C37—C38−0.4 (6)N1—C19—C20—C211.5 (5)
C37—N4—C36—C350.4 (5)C19—C20—C21—C22−1.5 (4)
C15—C1—C2—C3−2.3 (5)C19—C20—C21—C24176.8 (3)
C14—C1—C2—C11−1.2 (5)C20—C21—C24—C2541.2 (4)
C14—C1—C2—C3178.0 (3)C22—C21—C24—C2842.3 (4)
C2—C1—C14—C13−0.1 (5)C20—C21—C24—C28−136.0 (3)
C15—C1—C2—C11178.6 (3)C22—C21—C24—C25−140.5 (3)
C15—C1—C14—C13−179.9 (3)C20—C21—C22—C230.4 (4)
C1—C2—C11—C121.5 (4)C24—C21—C22—C23−177.9 (3)
C1—C2—C3—C4−179.0 (3)C21—C22—C23—N10.9 (5)
C11—C2—C3—C40.2 (5)C21—C24—C25—C26−178.8 (3)
C1—C2—C11—C10179.0 (3)C28—C24—C25—C26−1.5 (5)
C3—C2—C11—C10−0.2 (5)C25—C24—C28—C270.6 (5)
C3—C2—C11—C12−177.7 (3)C21—C24—C28—C27177.9 (3)
C2—C3—C4—C5179.3 (3)C24—C25—C26—N21.3 (5)
C2—C3—C4—C9−0.5 (5)N2—C27—C28—C240.8 (6)
C3—C4—C5—C17−0.9 (5)N3—C29—C30—C310.8 (5)
C9—C4—C5—C6−0.5 (5)C29—C30—C31—C320.4 (4)
C9—C4—C5—C17178.9 (3)C29—C30—C31—C34178.6 (3)
C3—C4—C9—C8−179.8 (3)C30—C31—C32—C33−1.7 (5)
C3—C4—C9—C100.7 (5)C34—C31—C32—C33−179.9 (3)
C5—C4—C9—C80.5 (4)C30—C31—C34—C3535.2 (4)
C3—C4—C5—C6179.7 (3)C30—C31—C34—C38−143.9 (3)
C5—C4—C9—C10−179.1 (3)C32—C31—C34—C35−146.7 (3)
C4—C5—C6—C70.0 (5)C32—C31—C34—C3834.3 (5)
C17—C5—C6—C7−179.4 (3)C31—C32—C33—N32.0 (6)
C5—C6—C7—C80.6 (6)C31—C34—C35—C36−179.9 (3)
C6—C7—C8—C9−0.7 (6)C38—C34—C35—C36−0.8 (4)
C7—C8—C9—C10179.6 (3)C31—C34—C38—C37180.0 (3)
C7—C8—C9—C40.2 (5)C35—C34—C38—C370.8 (5)
C4—C9—C10—C11−0.7 (5)C34—C35—C36—N40.1 (5)
C8—C9—C10—C11179.8 (3)N4—C37—C38—C34−0.3 (6)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1.
(DIEAAzopy) top
Crystal data top
C18H8I2·2(C10H8N4)Z = 4
Mr = 846.45F(000) = 1656
Monoclinic, C2/cDx = 1.638 Mg m−3
a = 16.0411 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 22.6435 (11) ŵ = 1.87 mm−1
c = 9.6728 (7) ÅT = 296 K
β = 102.322 (7)°Prism, orange
V = 3432.5 (4) Å30.36 × 0.34 × 0.17 mm
Data collection top
Radiation source: Enhance (Mo) X-ray Source3363 reflections with i > 2σ(i)
Graphite monochromatorRint = 0.022
ω scanθmax = 30.0°, θmin = 4.1°
Absorption correction: multi-scan
SADABS		h = −22→19
Tmin = 0.527, Tmax = 0.684k = −31→28
10609 measured reflectionsl = −12→13
5009 independent reflections
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.05 W = 1/[Σ2(FO2) + (0.0365P)2 + 0.6702P] WHERE P = (FO2 + 2FC2)/3
5009 reflections(Δ/σ)max = 0.001
218 parametersΔρmax = 0.67 e Å−3
0 restraintsΔρmin = −0.55 e Å−3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.11678 (2)0.03974 (2)0.47853 (2)0.06160 (10)
C10.10921 (17)0.24424 (14)0.4744 (3)0.0529 (10)
C20.05328 (16)0.27465 (11)0.3602 (3)0.0464 (8)
C30.000000.24495 (16)0.250000.0453 (11)
C40.000000.36717 (17)0.250000.0601 (15)
C50.05281 (18)0.33782 (12)0.3612 (3)0.0529 (10)
C60.1077 (2)0.36789 (16)0.4742 (4)0.0702 (13)
C70.1597 (2)0.33846 (16)0.5787 (4)0.0776 (14)
C80.1611 (2)0.27596 (15)0.5800 (4)0.0670 (12)
C90.11126 (17)0.18099 (14)0.4761 (3)0.0534 (10)
C100.11289 (18)0.12900 (15)0.4772 (3)0.0582 (11)
N10.12352 (16)0.91594 (13)0.4845 (3)0.0645 (10)
N20.12331 (18)0.73037 (15)0.4638 (3)0.0754 (11)
N30.16147 (18)0.70573 (14)0.5668 (3)0.0707 (11)
N40.1429 (3)0.52001 (17)0.5485 (6)0.1127 (18)
C110.12799 (18)0.79467 (14)0.4809 (4)0.0579 (11)
C120.15148 (19)0.82470 (14)0.6076 (3)0.0606 (11)
C130.1481 (2)0.88537 (14)0.6035 (4)0.0661 (11)
C140.1016 (2)0.88556 (17)0.3654 (4)0.0758 (14)
C150.1021 (2)0.82556 (16)0.3588 (4)0.0733 (12)
C160.1532 (2)0.64095 (15)0.5488 (5)0.0736 (13)
C170.1930 (2)0.60900 (16)0.6627 (5)0.0808 (14)
C180.1856 (3)0.54862 (18)0.6574 (7)0.103 (2)
C190.1052 (4)0.5503 (2)0.4359 (8)0.126 (3)
C200.1079 (3)0.6132 (2)0.4322 (6)0.0964 (19)
H30.000000.203900.250000.0540*
H40.000000.408200.250000.0720*
H60.107600.409000.475800.0840*
H70.195100.359300.651000.0930*
H80.197500.256200.653000.0800*
H120.169000.804600.692600.0730*
H130.163800.906000.688200.0790*
H140.085000.906500.281200.0910*
H150.085000.806100.272700.0880*
H170.224600.627600.742600.0970*
H180.212500.527000.736000.1240*
H190.076000.530100.356700.1510*
H200.080000.634300.353400.1160*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0794 (2)0.03990 (10)0.0647 (2)0.00480 (10)0.01380 (10)0.00560 (10)
C10.0621 (17)0.0388 (16)0.0575 (17)−0.0033 (12)0.0124 (14)0.0012 (13)
C20.0519 (14)0.0326 (14)0.0585 (16)−0.0024 (11)0.0201 (12)−0.0003 (12)
C30.055 (2)0.0273 (18)0.056 (2)0.00000.0174 (17)0.0000
C40.071 (3)0.0255 (19)0.087 (3)0.00000.024 (2)0.0000
C50.0595 (16)0.0325 (14)0.0699 (19)−0.0046 (12)0.0209 (14)−0.0055 (13)
C60.080 (2)0.0382 (18)0.090 (3)−0.0108 (15)0.013 (2)−0.0125 (17)
C70.090 (2)0.052 (2)0.082 (3)−0.0170 (18)−0.001 (2)−0.0147 (19)
C80.074 (2)0.054 (2)0.066 (2)−0.0045 (16)−0.0004 (16)0.0004 (16)
C90.0638 (17)0.0452 (18)0.0478 (16)−0.0003 (13)0.0046 (13)0.0063 (13)
C100.0702 (19)0.0476 (19)0.0547 (17)0.0019 (14)0.0086 (14)0.0053 (14)
N10.0780 (18)0.0491 (17)0.0694 (19)0.0110 (12)0.0222 (14)0.0076 (14)
N20.0756 (19)0.069 (2)0.082 (2)0.0067 (15)0.0180 (16)−0.0010 (17)
N30.0692 (17)0.066 (2)0.079 (2)−0.0010 (14)0.0207 (15)−0.0034 (16)
N40.105 (3)0.054 (2)0.170 (4)0.003 (2)0.009 (3)−0.007 (3)
C110.0605 (18)0.0404 (17)0.077 (2)0.0029 (13)0.0239 (16)−0.0023 (15)
C120.0741 (19)0.0506 (18)0.0571 (18)0.0047 (15)0.0141 (15)0.0101 (15)
C130.090 (2)0.0526 (19)0.0560 (19)−0.0001 (17)0.0165 (16)−0.0100 (16)
C140.098 (3)0.069 (2)0.061 (2)0.0105 (19)0.0182 (19)0.0121 (19)
C150.096 (2)0.066 (2)0.057 (2)0.0045 (19)0.0141 (18)−0.0108 (18)
C160.072 (2)0.0430 (18)0.114 (3)−0.0025 (16)0.038 (2)−0.011 (2)
C170.078 (2)0.052 (2)0.116 (3)0.0009 (17)0.029 (2)0.002 (2)
C180.094 (3)0.059 (3)0.156 (5)0.000 (2)0.025 (3)0.014 (3)
C190.136 (5)0.075 (4)0.152 (5)−0.008 (3)−0.005 (4)−0.032 (3)
C200.100 (3)0.065 (3)0.119 (4)0.007 (2)0.012 (3)0.003 (3)
Geometric parameters (Å, º) top
I1—C102.022 (3)C4—H40.9300
I1—N1i2.805 (3)C6—H60.9300
N1—C131.329 (5)C7—H70.9300
N1—C141.323 (5)C8—H80.9300
N2—N31.191 (4)C11—C121.382 (5)
N2—C111.466 (5)C11—C151.359 (5)
N3—C161.480 (5)C12—C131.375 (4)
N4—C191.320 (9)C14—C151.360 (5)
N4—C181.300 (8)C16—C171.358 (6)
C1—C21.441 (4)C16—C201.358 (7)
C1—C81.375 (5)C17—C181.372 (5)
C1—C91.433 (4)C19—C201.426 (6)
C2—C31.389 (3)C12—H120.9300
C2—C51.431 (4)C13—H130.9300
C4—C5ii1.388 (3)C14—H140.9300
C4—C51.388 (3)C15—H150.9300
C5—C61.422 (5)C17—H170.9300
C6—C71.342 (5)C18—H180.9300
C7—C81.415 (5)C19—H190.9300
C9—C101.178 (5)C20—H200.9300
C3—H30.9300
C10—I1—N1179.17 (10)N2—C11—C12125.9 (3)
C13—N1—C14117.3 (3)N2—C11—C15114.5 (3)
N3—N2—C11111.5 (3)C12—C11—C15119.5 (3)
N2—N3—C16110.4 (3)C11—C12—C13117.7 (3)
C18—N4—C19118.6 (4)N1—C13—C12123.2 (3)
C2—C1—C9119.7 (3)N1—C14—C15123.9 (4)
C8—C1—C9120.3 (3)C11—C15—C14118.5 (3)
C2—C1—C8120.0 (3)N3—C16—C17114.7 (4)
C1—C2—C3122.5 (3)N3—C16—C20125.1 (4)
C1—C2—C5118.4 (3)C17—C16—C20120.2 (4)
C3—C2—C5119.1 (3)C16—C17—C18118.6 (4)
C2—C3—C2ii122.1 (3)N4—C18—C17123.6 (5)
C5—C4—C5ii122.8 (3)N4—C19—C20121.9 (6)
C2—C5—C6118.7 (3)C16—C20—C19117.1 (5)
C4—C5—C6122.8 (3)C11—C12—H12121.00
C2—C5—C4118.5 (3)C13—C12—H12121.00
C5—C6—C7121.6 (3)N1—C13—H13118.00
C6—C7—C8120.6 (3)C12—C13—H13118.00
C1—C8—C7120.7 (3)N1—C14—H14118.00
C1—C9—C10179.9 (4)C15—C14—H14118.00
I1—C10—C9179.5 (3)C11—C15—H15121.00
C2ii—C3—H3119.00C14—C15—H15121.00
C2—C3—H3119.00C16—C17—H17121.00
C5—C4—H4119.00C18—C17—H17121.00
C5ii—C4—H4119.00N4—C18—H18118.00
C5—C6—H6119.00C17—C18—H18118.00
C7—C6—H6119.00N4—C19—H19119.00
C8—C7—H7120.00C20—C19—H19119.00
C6—C7—H7120.00C16—C20—H20121.00
C1—C8—H8120.00C19—C20—H20121.00
C7—C8—H8120.00
C14—N1—C13—C12−0.1 (5)C3—C2—C5—C4−1.2 (4)
C13—N1—C14—C150.7 (5)C5ii—C4—C5—C6179.2 (3)
C11—N2—N3—C16178.0 (3)C5ii—C4—C5—C20.6 (3)
N3—N2—C11—C15166.5 (3)C2—C5—C6—C70.3 (5)
N3—N2—C11—C12−17.0 (5)C4—C5—C6—C7−178.3 (3)
N2—N3—C16—C17−178.4 (3)C5—C6—C7—C8−0.4 (5)
N2—N3—C16—C20−0.6 (5)C6—C7—C8—C1−0.1 (5)
C19—N4—C18—C170.8 (8)N2—C11—C12—C13−176.9 (3)
C18—N4—C19—C20−1.9 (9)C15—C11—C12—C13−0.6 (5)
C9—C1—C2—C30.3 (4)N2—C11—C15—C14177.8 (3)
C8—C1—C2—C3179.4 (3)C12—C11—C15—C141.1 (5)
C8—C1—C2—C5−0.7 (4)C11—C12—C13—N10.0 (5)
C2—C1—C8—C70.6 (5)N1—C14—C15—C11−1.2 (5)
C9—C1—C8—C7179.7 (3)N3—C16—C17—C18177.3 (4)
C9—C1—C2—C5−179.8 (3)C20—C16—C17—C18−0.6 (6)
C1—C2—C3—C2ii−179.5 (2)N3—C16—C20—C19−178.2 (4)
C1—C2—C5—C4178.9 (2)C17—C16—C20—C19−0.5 (7)
C1—C2—C5—C60.3 (4)C16—C17—C18—N40.5 (7)
C5—C2—C3—C2ii0.6 (3)N4—C19—C20—C161.8 (9)
C3—C2—C5—C6−179.8 (2)
Symmetry codes: (i) x, y−1, z; (ii) −x, y, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···I1iii0.933.304.131 (3)150
C14—H14···I1iv0.933.314.160 (4)153
Symmetry codes: (iii) x, −y+1, z+1/2; (iv) x, −y+1, z−1/2.
(DIEABipyNO) TW-10-45 1,8-di(iodoethynyl)anthracene, (4,4'-bipyridyl-1-oxide)2 top
Crystal data top
(C18H8I2)(C10H8N2O)2Z = 2
Mr = 822.41F(000) = 804
Triclinic, P1Dx = 1.712 Mg m−3
a = 9.6027 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.0523 (19) ÅCell parameters from 9981 reflections
c = 18.021 (4) Åθ = 2.3–32.6°
α = 85.600 (5)°µ = 2.01 mm−1
β = 80.043 (5)°T = 120 K
γ = 68.603 (5)°Prism, orange
V = 1595.0 (5) Å30.30 × 0.24 × 0.14 mm
Data collection top
Bruker APEX-II CCD
diffractometer		10024 reflections with I > 2σ(I)
φ and ω scansRint = 0.036
Absorption correction: multi-scan
SADABS		θmax = 32.7°, θmin = 2.2°
Tmin = 0.592, Tmax = 0.766h = −14→14
45988 measured reflectionsk = −15→14
10925 independent reflectionsl = −26→26
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.030P)2 + 3.5P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.001
10925 reflectionsΔρmax = 1.95 e Å−3
415 parametersΔρmin = −1.38 e Å−3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C110.7590 (3)0.2928 (3)0.15396 (15)0.0222 (4)
C120.6999 (3)0.4466 (3)0.14743 (15)0.0237 (5)
C130.6640 (3)0.5109 (3)0.07985 (16)0.0289 (5)
H130.62400.61210.07590.035*
C140.6859 (4)0.4278 (3)0.01612 (17)0.0308 (6)
H140.66140.4742−0.03030.037*
C150.7417 (3)0.2823 (3)0.02010 (16)0.0281 (5)
H150.75540.2284−0.02340.034*
C160.7794 (3)0.2108 (3)0.08902 (15)0.0234 (5)
C170.8364 (3)0.0615 (3)0.09482 (15)0.0257 (5)
H170.85020.00630.05180.031*
C180.8730 (3)−0.0074 (3)0.16268 (16)0.0241 (5)
C190.9262 (3)−0.1600 (3)0.16951 (17)0.0281 (5)
H190.9393−0.21590.12690.034*
C200.9578 (4)−0.2249 (3)0.23657 (18)0.0316 (6)
H200.9913−0.32620.24050.038*
C210.9416 (3)−0.1447 (3)0.30072 (17)0.0293 (5)
H210.9658−0.19290.34680.035*
C220.8915 (3)0.0023 (3)0.29726 (15)0.0244 (5)
C230.8538 (3)0.0750 (3)0.22734 (15)0.0219 (4)
C240.7975 (3)0.2221 (3)0.22171 (15)0.0231 (5)
H240.78460.27690.26480.028*
C310.6809 (3)0.5278 (3)0.21282 (16)0.0256 (5)
C320.6709 (3)0.5827 (3)0.27121 (16)0.0276 (5)
I10.64725 (2)0.67094 (2)0.37201 (2)0.02641 (5)
C410.8771 (3)0.0835 (3)0.36170 (16)0.0258 (5)
C420.8657 (3)0.1561 (3)0.41419 (16)0.0282 (5)
I20.83599 (2)0.28213 (2)0.50214 (2)0.02591 (5)
N510.6204 (3)0.7932 (3)0.50511 (15)0.0323 (5)
C520.5334 (3)0.7748 (3)0.56815 (18)0.0314 (6)
H520.47510.71670.56660.038*
C530.5242 (3)0.8366 (3)0.63581 (16)0.0260 (5)
H530.45890.82260.67920.031*
C540.6119 (3)0.9195 (3)0.63965 (15)0.0221 (4)
C550.7025 (4)0.9375 (3)0.57377 (17)0.0310 (6)
H550.76430.99290.57360.037*
C560.7021 (4)0.8744 (4)0.50860 (17)0.0346 (6)
H560.76320.88960.46380.042*
N610.6083 (3)1.1010 (3)0.84562 (17)0.0373 (6)
O610.6095 (3)1.1547 (4)0.90834 (17)0.0599 (9)
C620.4805 (3)1.0890 (3)0.83063 (17)0.0292 (5)
H620.38991.12180.86600.035*
C630.4808 (3)1.0297 (3)0.76443 (15)0.0242 (5)
H630.39051.02020.75520.029*
C640.6103 (3)0.9832 (3)0.71063 (15)0.0237 (5)
C650.7393 (3)0.9986 (4)0.7281 (2)0.0370 (7)
H650.83040.96900.69300.044*
C660.7368 (4)1.0556 (5)0.7950 (2)0.0465 (9)
H660.82661.06350.80610.056*
N710.7946 (3)0.4552 (3)0.62311 (15)0.0324 (5)
C720.6926 (4)0.4527 (4)0.68331 (19)0.0364 (7)
H720.62670.40290.68000.044*
C730.6780 (3)0.5190 (4)0.75021 (17)0.0314 (6)
H730.60230.51600.79120.038*
C740.7751 (3)0.5898 (3)0.75690 (16)0.0253 (5)
C750.8801 (3)0.5941 (3)0.69374 (17)0.0292 (5)
H750.94750.64310.69510.035*
C760.8849 (3)0.5259 (3)0.62888 (17)0.0292 (5)
H760.95690.53000.58620.035*
N810.7767 (4)0.7554 (4)0.96622 (16)0.0399 (6)
O810.7813 (4)0.8005 (4)1.03040 (16)0.0539 (8)
C820.6420 (4)0.7807 (4)0.94229 (18)0.0348 (6)
H820.55000.83510.97240.042*
C830.6386 (3)0.7277 (3)0.87486 (17)0.0303 (6)
H830.54400.74390.85940.036*
C840.7729 (3)0.6504 (3)0.82874 (16)0.0276 (5)
C850.9084 (4)0.6282 (4)0.8553 (2)0.0384 (7)
H851.00230.57700.82550.046*
C860.9075 (4)0.6794 (5)0.9237 (2)0.0443 (8)
H861.00050.66090.94140.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0208 (10)0.0234 (11)0.0230 (11)−0.0087 (9)−0.0009 (8)−0.0061 (9)
C120.0241 (11)0.0244 (12)0.0233 (11)−0.0095 (9)−0.0016 (9)−0.0055 (9)
C130.0327 (13)0.0274 (13)0.0258 (13)−0.0090 (11)−0.0051 (10)−0.0037 (10)
C140.0349 (14)0.0352 (15)0.0242 (13)−0.0132 (12)−0.0086 (11)−0.0002 (10)
C150.0308 (13)0.0342 (14)0.0231 (12)−0.0145 (11)−0.0045 (10)−0.0070 (10)
C160.0244 (11)0.0257 (12)0.0230 (11)−0.0121 (9)−0.0023 (9)−0.0058 (9)
C170.0269 (12)0.0299 (13)0.0226 (12)−0.0123 (10)−0.0014 (9)−0.0087 (9)
C180.0227 (11)0.0235 (12)0.0274 (12)−0.0097 (9)−0.0008 (9)−0.0073 (9)
C190.0277 (12)0.0252 (13)0.0319 (14)−0.0093 (10)−0.0020 (10)−0.0091 (10)
C200.0339 (14)0.0223 (12)0.0358 (15)−0.0065 (10)−0.0046 (11)−0.0052 (11)
C210.0306 (13)0.0275 (13)0.0292 (13)−0.0094 (10)−0.0044 (10)−0.0022 (10)
C220.0219 (11)0.0256 (12)0.0248 (12)−0.0076 (9)−0.0019 (9)−0.0037 (9)
C230.0205 (10)0.0212 (11)0.0244 (11)−0.0083 (8)−0.0005 (8)−0.0055 (9)
C240.0215 (10)0.0263 (12)0.0230 (11)−0.0099 (9)0.0002 (9)−0.0110 (9)
C310.0259 (12)0.0228 (12)0.0269 (12)−0.0072 (9)−0.0029 (9)−0.0038 (9)
C320.0304 (13)0.0229 (12)0.0284 (13)−0.0082 (10)−0.0028 (10)−0.0045 (10)
I10.02845 (9)0.02456 (9)0.02333 (9)−0.00477 (6)−0.00435 (6)−0.00637 (6)
C410.0236 (11)0.0276 (13)0.0256 (12)−0.0089 (10)−0.0032 (9)−0.0007 (10)
C420.0291 (13)0.0302 (13)0.0249 (12)−0.0103 (10)−0.0035 (10)−0.0019 (10)
I20.02921 (9)0.02750 (9)0.02271 (8)−0.01154 (7)−0.00415 (6)−0.00317 (6)
N510.0346 (12)0.0324 (13)0.0258 (11)−0.0050 (10)−0.0063 (9)−0.0093 (9)
C520.0279 (13)0.0347 (15)0.0323 (14)−0.0096 (11)−0.0049 (11)−0.0117 (11)
C530.0227 (11)0.0285 (13)0.0271 (12)−0.0089 (10)−0.0020 (9)−0.0072 (10)
C540.0225 (11)0.0187 (11)0.0230 (11)−0.0042 (8)−0.0028 (9)−0.0060 (8)
C550.0381 (15)0.0281 (13)0.0282 (13)−0.0156 (11)0.0020 (11)−0.0050 (10)
C560.0415 (16)0.0347 (15)0.0241 (13)−0.0118 (13)0.0028 (11)−0.0061 (11)
N610.0293 (12)0.0463 (16)0.0376 (14)−0.0115 (11)−0.0027 (10)−0.0238 (12)
O610.0397 (13)0.093 (2)0.0505 (16)−0.0216 (15)−0.0006 (12)−0.0493 (17)
C620.0237 (12)0.0331 (14)0.0293 (13)−0.0072 (10)−0.0025 (10)−0.0110 (11)
C630.0207 (11)0.0242 (12)0.0264 (12)−0.0056 (9)−0.0034 (9)−0.0061 (9)
C640.0231 (11)0.0212 (11)0.0262 (12)−0.0066 (9)−0.0028 (9)−0.0066 (9)
C650.0248 (13)0.0462 (18)0.0422 (17)−0.0152 (12)0.0050 (12)−0.0243 (14)
C660.0267 (14)0.066 (2)0.051 (2)−0.0182 (15)0.0010 (13)−0.0329 (19)
N710.0328 (12)0.0340 (13)0.0302 (12)−0.0114 (10)−0.0023 (10)−0.0091 (10)
C720.0328 (14)0.0443 (18)0.0360 (16)−0.0180 (13)−0.0012 (12)−0.0124 (13)
C730.0260 (12)0.0399 (16)0.0300 (14)−0.0147 (11)0.0013 (10)−0.0080 (11)
C740.0242 (11)0.0221 (12)0.0284 (13)−0.0063 (9)−0.0038 (9)−0.0043 (9)
C750.0300 (13)0.0265 (13)0.0319 (14)−0.0117 (10)−0.0021 (11)−0.0036 (10)
C760.0335 (13)0.0264 (13)0.0259 (13)−0.0096 (11)−0.0008 (10)−0.0034 (10)
N810.0516 (17)0.0521 (18)0.0291 (13)−0.0345 (15)−0.0011 (12)−0.0092 (12)
O810.0607 (17)0.075 (2)0.0369 (14)−0.0380 (16)0.0047 (12)−0.0255 (13)
C820.0399 (16)0.0335 (15)0.0298 (14)−0.0138 (12)0.0018 (12)−0.0074 (11)
C830.0312 (13)0.0293 (14)0.0283 (13)−0.0083 (11)−0.0036 (10)−0.0031 (10)
C840.0290 (12)0.0276 (13)0.0285 (13)−0.0133 (10)−0.0021 (10)−0.0025 (10)
C850.0327 (15)0.051 (2)0.0370 (16)−0.0212 (14)−0.0007 (12)−0.0127 (14)
C860.0386 (17)0.066 (2)0.0390 (18)−0.0305 (17)−0.0024 (14)−0.0117 (16)
Geometric parameters (Å, º) top
C11—C241.401 (4)C54—C551.387 (4)
C11—C161.427 (4)C54—C641.469 (4)
C11—C121.443 (4)C55—C561.378 (4)
C12—C131.372 (4)C55—H550.9500
C12—C311.433 (4)C56—H560.9500
C13—C141.412 (4)N61—O611.293 (3)
C13—H130.9500N61—C621.349 (4)
C14—C151.363 (4)N61—C661.352 (4)
C14—H140.9500C62—C631.373 (4)
C15—C161.421 (4)C62—H620.9500
C15—H150.9500C63—C641.391 (4)
C16—C171.400 (4)C63—H630.9500
C17—C181.393 (4)C64—C651.393 (4)
C17—H170.9500C65—C661.366 (4)
C18—C231.428 (4)C65—H650.9500
C18—C191.432 (4)C66—H660.9500
C19—C201.356 (4)N71—C761.327 (4)
C19—H190.9500N71—C721.335 (4)
C20—C211.415 (4)C72—C731.383 (4)
C20—H200.9500C72—H720.9500
C21—C221.377 (4)C73—C741.389 (4)
C21—H210.9500C73—H730.9500
C22—C411.429 (4)C74—C751.393 (4)
C22—C231.441 (4)C74—C841.466 (4)
C23—C241.380 (4)C75—C761.385 (4)
C24—H240.9500C75—H750.9500
C31—C321.199 (4)C76—H760.9500
C32—I12.023 (3)N81—O811.288 (4)
I1—N512.709 (3)N81—C861.343 (5)
C41—C421.205 (4)N81—C821.364 (5)
C42—I22.021 (3)C82—C831.373 (4)
I2—N712.778 (3)C82—H820.9500
N51—C521.332 (4)C83—C841.398 (4)
N51—C561.333 (4)C83—H830.9500
C52—C531.385 (4)C84—C851.400 (4)
C52—H520.9500C85—C861.369 (5)
C53—C541.396 (4)C85—H850.9500
C53—H530.9500C86—H860.9500
C24—C11—C16119.4 (2)C56—C55—C54119.4 (3)
C24—C11—C12122.0 (2)C56—C55—H55120.3
C16—C11—C12118.6 (2)C54—C55—H55120.3
C13—C12—C31121.9 (3)N51—C56—C55123.5 (3)
C13—C12—C11119.9 (2)N51—C56—H56118.3
C31—C12—C11118.2 (2)C55—C56—H56118.3
C12—C13—C14120.6 (3)O61—N61—C62120.6 (3)
C12—C13—H13119.7O61—N61—C66119.4 (3)
C14—C13—H13119.7C62—N61—C66119.9 (3)
C15—C14—C13121.2 (3)N61—C62—C63120.2 (3)
C15—C14—H14119.4N61—C62—H62119.9
C13—C14—H14119.4C63—C62—H62119.9
C14—C15—C16120.3 (3)C62—C63—C64121.5 (3)
C14—C15—H15119.9C62—C63—H63119.2
C16—C15—H15119.9C64—C63—H63119.2
C17—C16—C15121.5 (2)C63—C64—C65116.3 (2)
C17—C16—C11119.1 (2)C63—C64—C54121.9 (2)
C15—C16—C11119.4 (3)C65—C64—C54121.7 (2)
C18—C17—C16121.0 (2)C66—C65—C64121.1 (3)
C18—C17—H17119.5C66—C65—H65119.5
C16—C17—H17119.5C64—C65—H65119.5
C17—C18—C23119.8 (2)N61—C66—C65120.9 (3)
C17—C18—C19121.2 (2)N61—C66—H66119.5
C23—C18—C19119.1 (3)C65—C66—H66119.5
C20—C19—C18120.3 (3)C76—N71—C72117.3 (3)
C20—C19—H19119.9C76—N71—I2123.2 (2)
C18—C19—H19119.9C72—N71—I2118.8 (2)
C19—C20—C21121.2 (3)N71—C72—C73123.3 (3)
C19—C20—H20119.4N71—C72—H72118.3
C21—C20—H20119.4C73—C72—H72118.3
C22—C21—C20121.0 (3)C72—C73—C74119.4 (3)
C22—C21—H21119.5C72—C73—H73120.3
C20—C21—H21119.5C74—C73—H73120.3
C21—C22—C41121.1 (3)C73—C74—C75117.2 (3)
C21—C22—C23119.3 (2)C73—C74—C84121.2 (3)
C41—C22—C23119.6 (2)C75—C74—C84121.4 (3)
C24—C23—C18119.3 (2)C76—C75—C74119.1 (3)
C24—C23—C22121.6 (2)C76—C75—H75120.4
C18—C23—C22119.2 (2)C74—C75—H75120.4
C23—C24—C11121.5 (2)N71—C76—C75123.6 (3)
C23—C24—H24119.2N71—C76—H76118.2
C11—C24—H24119.2C75—C76—H76118.2
C32—C31—C12173.3 (3)O81—N81—C86118.7 (3)
C31—C32—I1177.3 (3)O81—N81—C82121.0 (3)
C32—I1—N51178.39 (11)C86—N81—C82120.3 (3)
C42—C41—C22177.5 (3)N81—C82—C83120.4 (3)
C41—C42—I2177.3 (3)N81—C82—H82119.8
C42—I2—N71179.87 (11)C83—C82—H82119.8
C52—N51—C56117.5 (3)C82—C83—C84120.7 (3)
C52—N51—I1124.3 (2)C82—C83—H83119.6
C56—N51—I1118.2 (2)C84—C83—H83119.6
N51—C52—C53123.0 (3)C83—C84—C85116.9 (3)
N51—C52—H52118.5C83—C84—C74122.8 (3)
C53—C52—H52118.5C85—C84—C74120.3 (3)
C52—C53—C54119.4 (3)C86—C85—C84120.9 (3)
C52—C53—H53120.3C86—C85—H85119.6
C54—C53—H53120.3C84—C85—H85119.6
C55—C54—C53117.2 (2)N81—C86—C85120.9 (3)
C55—C54—C64121.3 (2)N81—C86—H86119.6
C53—C54—C64121.6 (2)C85—C86—H86119.6
C24—C11—C12—C13179.9 (3)C64—C54—C55—C56179.2 (3)
C16—C11—C12—C130.3 (4)C52—N51—C56—C551.1 (5)
C24—C11—C12—C310.1 (4)I1—N51—C56—C55−177.4 (3)
C16—C11—C12—C31−179.6 (2)C54—C55—C56—N51−1.3 (5)
C31—C12—C13—C14179.1 (3)O61—N61—C62—C63−178.9 (3)
C11—C12—C13—C14−0.7 (4)C66—N61—C62—C630.6 (5)
C12—C13—C14—C150.7 (5)N61—C62—C63—C64−1.3 (5)
C13—C14—C15—C16−0.1 (5)C62—C63—C64—C650.8 (4)
C14—C15—C16—C17179.7 (3)C62—C63—C64—C54180.0 (3)
C14—C15—C16—C11−0.3 (4)C55—C54—C64—C63147.6 (3)
C24—C11—C16—C170.5 (4)C53—C54—C64—C63−33.5 (4)
C12—C11—C16—C17−179.8 (2)C55—C54—C64—C65−33.3 (4)
C24—C11—C16—C15−179.4 (2)C53—C54—C64—C65145.7 (3)
C12—C11—C16—C150.2 (4)C63—C64—C65—C660.4 (5)
C15—C16—C17—C18180.0 (3)C54—C64—C65—C66−178.8 (4)
C11—C16—C17—C180.0 (4)O61—N61—C66—C65−179.9 (4)
C16—C17—C18—C23−0.6 (4)C62—N61—C66—C650.6 (6)
C16—C17—C18—C19177.7 (3)C64—C65—C66—N61−1.1 (7)
C17—C18—C19—C20−178.4 (3)C76—N71—C72—C73−0.3 (5)
C23—C18—C19—C20−0.1 (4)I2—N71—C72—C73170.7 (3)
C18—C19—C20—C21−1.0 (5)N71—C72—C73—C74−1.3 (5)
C19—C20—C21—C220.8 (5)C72—C73—C74—C752.1 (5)
C20—C21—C22—C41−179.1 (3)C72—C73—C74—C84−174.5 (3)
C20—C21—C22—C230.6 (4)C73—C74—C75—C76−1.4 (4)
C17—C18—C23—C240.6 (4)C84—C74—C75—C76175.2 (3)
C19—C18—C23—C24−177.7 (2)C72—N71—C76—C751.1 (5)
C17—C18—C23—C22179.7 (2)I2—N71—C76—C75−169.5 (2)
C19—C18—C23—C221.4 (4)C74—C75—C76—N71−0.2 (5)
C21—C22—C23—C24177.4 (3)O81—N81—C82—C83−177.8 (3)
C41—C22—C23—C24−2.8 (4)C86—N81—C82—C830.5 (5)
C21—C22—C23—C18−1.6 (4)N81—C82—C83—C84−1.7 (5)
C41—C22—C23—C18178.1 (2)C82—C83—C84—C851.1 (5)
C18—C23—C24—C11−0.1 (4)C82—C83—C84—C74179.0 (3)
C22—C23—C24—C11−179.2 (2)C73—C74—C84—C83−44.0 (4)
C16—C11—C24—C23−0.5 (4)C75—C74—C84—C83139.6 (3)
C12—C11—C24—C23179.9 (2)C73—C74—C84—C85133.8 (3)
C56—N51—C52—C530.4 (5)C75—C74—C84—C85−42.6 (4)
I1—N51—C52—C53178.7 (2)C83—C84—C85—C860.6 (5)
N51—C52—C53—C54−1.5 (5)C74—C84—C85—C86−177.3 (3)
C52—C53—C54—C551.2 (4)O81—N81—C86—C85179.5 (4)
C52—C53—C54—C64−177.8 (3)C82—N81—C86—C851.2 (6)
C53—C54—C55—C560.1 (4)C84—C85—C86—N81−1.8 (6)
(DIEABpe) TW-10-14 1,8-di(iodoethynyl)anthracene, 1,2-bis(4-pyridyl)ethane top
Crystal data top
(C18H8I2)(C12H12N2)Z = 2
Mr = 662.28F(000) = 640
Triclinic, P1Dx = 1.734 Mg m−3
a = 9.5153 (16) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.6261 (16) ÅCell parameters from 9607 reflections
c = 14.368 (3) Åθ = 2.2–32.5°
α = 96.346 (5)°µ = 2.50 mm−1
β = 93.215 (5)°T = 120 K
γ = 103.295 (4)°Prism, bronze
V = 1268.4 (4) Å30.40 × 0.28 × 0.14 mm
Data collection top
Bruker APEX-II CCD
diffractometer		7891 reflections with I > 2σ(I)
φ and ω scansRint = 0.032
Absorption correction: multi-scan
SADABS		θmax = 32.5°, θmin = 2.2°
Tmin = 0.595, Tmax = 0.721h = −14→14
38542 measured reflectionsk = −13→14
8522 independent reflectionsl = −21→20
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.067 w = 1/[σ2(Fo2) + (0.030P)2 + 1.P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
8522 reflectionsΔρmax = 1.48 e Å−3
307 parametersΔρmin = −0.85 e Å−3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C110.51557 (19)−0.08715 (19)0.39395 (12)0.0216 (3)
C120.6412 (2)0.0273 (2)0.38789 (12)0.0235 (3)
C130.7757 (2)0.0183 (2)0.42377 (14)0.0281 (4)
H130.85790.09410.41950.034*
C140.7926 (2)−0.1029 (2)0.46702 (15)0.0313 (4)
H140.8859−0.10690.49220.038*
C150.6769 (2)−0.2133 (2)0.47287 (14)0.0304 (4)
H150.6905−0.29410.50150.036*
C160.5348 (2)−0.2100 (2)0.43662 (13)0.0251 (3)
C170.4150 (2)−0.3220 (2)0.44240 (14)0.0273 (4)
H170.4282−0.40390.47000.033*
C180.2760 (2)−0.31717 (19)0.40873 (13)0.0244 (3)
C190.1523 (2)−0.4314 (2)0.41500 (14)0.0291 (4)
H190.1644−0.51390.44220.035*
C200.0175 (2)−0.4239 (2)0.38256 (15)0.0298 (4)
H20−0.0633−0.50150.38670.036*
C21−0.0033 (2)−0.3015 (2)0.34285 (14)0.0273 (3)
H21−0.0982−0.29790.32060.033*
C220.1117 (2)−0.18721 (19)0.33584 (13)0.0234 (3)
C230.25642 (19)−0.19285 (18)0.36762 (12)0.0216 (3)
C240.37687 (19)−0.08126 (19)0.36047 (12)0.0220 (3)
H240.36410.00020.33230.026*
C310.6273 (2)0.1492 (2)0.34253 (13)0.0251 (3)
C320.6185 (2)0.2497 (2)0.30121 (14)0.0278 (4)
I10.61962 (2)0.41887 (2)0.22996 (2)0.02785 (4)
C410.0904 (2)−0.0613 (2)0.29833 (13)0.0248 (3)
C420.0806 (2)0.0495 (2)0.26973 (14)0.0275 (3)
I20.07998 (2)0.23912 (2)0.22174 (2)0.02796 (4)
N510.6470 (2)0.66039 (19)0.13306 (13)0.0324 (4)
C520.6391 (2)0.6643 (2)0.04022 (16)0.0352 (4)
H520.61890.5758−0.00020.042*
C530.6589 (2)0.7913 (3)0.00002 (15)0.0351 (4)
H530.65150.7886−0.06640.042*
C540.6896 (2)0.9218 (2)0.05726 (15)0.0311 (4)
C550.7006 (2)0.9175 (2)0.15287 (15)0.0304 (4)
H550.72381.00440.19500.037*
C560.6779 (2)0.7871 (2)0.18713 (14)0.0307 (4)
H560.68460.78720.25340.037*
C570.7144 (3)1.0671 (3)0.0218 (2)0.0470 (6)
H57A0.61921.08360.00120.056*
H57B0.75801.14230.07480.056*
N610.8927 (2)1.50111 (19)−0.15155 (13)0.0319 (4)
C620.9984 (3)1.4471 (2)−0.11592 (16)0.0361 (4)
H621.09521.5031−0.11210.043*
C630.9737 (3)1.3136 (3)−0.08434 (17)0.0395 (5)
H631.05271.2794−0.06030.047*
C640.8349 (3)1.2307 (2)−0.08775 (18)0.0405 (5)
C650.7244 (3)1.2865 (2)−0.12439 (18)0.0394 (5)
H650.62661.2331−0.12810.047*
C660.7576 (3)1.4201 (2)−0.15542 (16)0.0347 (4)
H660.68071.4561−0.18070.042*
C670.8063 (4)1.0846 (3)−0.0550 (3)0.0743 (12)
H67A0.76081.0118−0.10880.089*
H67B0.90031.0647−0.03530.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0276 (8)0.0214 (7)0.0182 (7)0.0094 (6)0.0047 (6)0.0034 (6)
C120.0278 (8)0.0236 (8)0.0207 (7)0.0087 (6)0.0053 (6)0.0032 (6)
C130.0269 (8)0.0314 (9)0.0259 (8)0.0082 (7)0.0026 (7)0.0000 (7)
C140.0317 (9)0.0353 (10)0.0296 (9)0.0160 (8)−0.0019 (7)0.0008 (8)
C150.0371 (10)0.0297 (9)0.0289 (9)0.0177 (8)−0.0001 (7)0.0049 (7)
C160.0321 (9)0.0237 (8)0.0230 (8)0.0127 (7)0.0032 (7)0.0044 (6)
C170.0369 (9)0.0229 (8)0.0260 (8)0.0128 (7)0.0041 (7)0.0073 (7)
C180.0339 (9)0.0200 (7)0.0218 (8)0.0097 (6)0.0063 (7)0.0050 (6)
C190.0392 (10)0.0207 (8)0.0286 (9)0.0067 (7)0.0060 (7)0.0081 (7)
C200.0363 (10)0.0221 (8)0.0309 (9)0.0041 (7)0.0071 (8)0.0064 (7)
C210.0298 (9)0.0237 (8)0.0285 (9)0.0060 (7)0.0030 (7)0.0041 (7)
C220.0280 (8)0.0203 (7)0.0230 (8)0.0069 (6)0.0035 (6)0.0041 (6)
C230.0286 (8)0.0196 (7)0.0186 (7)0.0085 (6)0.0049 (6)0.0035 (6)
C240.0281 (8)0.0205 (7)0.0198 (7)0.0092 (6)0.0041 (6)0.0053 (6)
C310.0256 (8)0.0252 (8)0.0242 (8)0.0047 (6)0.0050 (6)0.0033 (6)
C320.0292 (9)0.0251 (8)0.0287 (9)0.0038 (7)0.0054 (7)0.0054 (7)
I10.03187 (7)0.02183 (6)0.03057 (7)0.00462 (4)0.00670 (5)0.00819 (4)
C410.0261 (8)0.0221 (8)0.0266 (8)0.0064 (6)0.0030 (6)0.0036 (6)
C420.0300 (9)0.0237 (8)0.0300 (9)0.0080 (7)0.0031 (7)0.0050 (7)
I20.03624 (7)0.02031 (6)0.03083 (7)0.01101 (5)0.00652 (5)0.00736 (4)
N510.0417 (9)0.0235 (8)0.0351 (9)0.0087 (7)0.0137 (7)0.0094 (7)
C520.0386 (10)0.0285 (10)0.0334 (10)−0.0015 (8)0.0084 (8)−0.0013 (8)
C530.0373 (10)0.0442 (12)0.0240 (9)0.0076 (9)0.0034 (8)0.0096 (8)
C540.0324 (9)0.0316 (10)0.0358 (10)0.0130 (8)0.0132 (8)0.0162 (8)
C550.0358 (10)0.0244 (9)0.0321 (10)0.0076 (7)0.0081 (8)0.0046 (7)
C560.0400 (10)0.0300 (9)0.0254 (9)0.0126 (8)0.0056 (7)0.0067 (7)
C570.0652 (16)0.0375 (12)0.0511 (14)0.0242 (11)0.0283 (13)0.0242 (11)
N610.0450 (10)0.0241 (8)0.0306 (8)0.0113 (7)0.0122 (7)0.0090 (6)
C620.0379 (11)0.0347 (11)0.0389 (11)0.0099 (8)0.0121 (9)0.0121 (9)
C630.0475 (12)0.0424 (12)0.0401 (12)0.0238 (10)0.0185 (10)0.0202 (10)
C640.0591 (14)0.0277 (10)0.0463 (13)0.0207 (9)0.0338 (11)0.0184 (9)
C650.0416 (11)0.0276 (10)0.0497 (13)0.0056 (8)0.0176 (10)0.0066 (9)
C660.0431 (11)0.0313 (10)0.0339 (10)0.0141 (8)0.0078 (8)0.0088 (8)
C670.106 (3)0.0395 (14)0.107 (3)0.0430 (16)0.081 (2)0.0458 (17)
Geometric parameters (Å, º) top
C11—C241.395 (2)C42—I22.0219 (19)
C11—C161.434 (2)N51—C561.333 (3)
C11—C121.441 (3)N51—C521.337 (3)
C12—C131.377 (3)C52—C531.387 (3)
C12—C311.432 (3)C52—H520.9500
C13—C141.417 (3)C53—C541.384 (3)
C13—H130.9500C53—H530.9500
C14—C151.357 (3)C54—C551.378 (3)
C14—H140.9500C54—C571.513 (3)
C15—C161.430 (3)C55—C561.375 (3)
C15—H150.9500C55—H550.9500
C16—C171.390 (3)C56—H560.9500
C17—C181.396 (3)C57—C671.446 (4)
C17—H170.9500C57—H57A0.9900
C18—C191.428 (3)C57—H57B0.9900
C18—C231.436 (2)N61—C661.336 (3)
C19—C201.361 (3)N61—C621.336 (3)
C19—H190.9500N61—I2i2.7614 (17)
C20—C211.412 (3)C62—C631.384 (3)
C20—H200.9500C62—H620.9500
C21—C221.379 (3)C63—C641.372 (4)
C21—H210.9500C63—H630.9500
C22—C411.430 (2)C64—C651.390 (4)
C22—C231.441 (2)C64—C671.502 (3)
C23—C241.396 (3)C65—C661.381 (3)
C24—H240.9500C65—H650.9500
C31—C321.206 (3)C66—H660.9500
C32—I12.016 (2)C67—H67A0.9900
I1—N512.8088 (18)C67—H67B0.9900
C41—C421.206 (3)
C24—C11—C16119.39 (17)C56—N51—I1115.29 (13)
C24—C11—C12122.15 (16)C52—N51—I1128.26 (14)
C16—C11—C12118.46 (16)N51—C52—C53123.2 (2)
C13—C12—C31119.71 (18)N51—C52—H52118.4
C13—C12—C11120.15 (17)C53—C52—H52118.4
C31—C12—C11120.12 (16)C54—C53—C52119.61 (19)
C12—C13—C14120.74 (19)C54—C53—H53120.2
C12—C13—H13119.6C52—C53—H53120.2
C14—C13—H13119.6C55—C54—C53117.03 (18)
C15—C14—C13120.60 (18)C55—C54—C57118.5 (2)
C15—C14—H14119.7C53—C54—C57124.5 (2)
C13—C14—H14119.7C56—C55—C54119.76 (19)
C14—C15—C16121.11 (18)C56—C55—H55120.1
C14—C15—H15119.4C54—C55—H55120.1
C16—C15—H15119.4N51—C56—C55123.97 (19)
C17—C16—C15121.79 (17)N51—C56—H56118.0
C17—C16—C11119.28 (17)C55—C56—H56118.0
C15—C16—C11118.92 (18)C67—C57—C54115.2 (2)
C16—C17—C18121.67 (17)C67—C57—H57A108.5
C16—C17—H17119.2C54—C57—H57A108.5
C18—C17—H17119.2C67—C57—H57B108.5
C17—C18—C19121.97 (17)C54—C57—H57B108.5
C17—C18—C23119.01 (17)H57A—C57—H57B107.5
C19—C18—C23119.02 (17)C66—N61—C62116.91 (18)
C20—C19—C18121.03 (17)C66—N61—I2i115.46 (14)
C20—C19—H19119.5C62—N61—I2i127.63 (15)
C18—C19—H19119.5N61—C62—C63123.3 (2)
C19—C20—C21120.46 (18)N61—C62—H62118.4
C19—C20—H20119.8C63—C62—H62118.4
C21—C20—H20119.8C64—C63—C62119.9 (2)
C22—C21—C20121.14 (18)C64—C63—H63120.1
C22—C21—H21119.4C62—C63—H63120.1
C20—C21—H21119.4C63—C64—C65117.1 (2)
C21—C22—C41121.28 (17)C63—C64—C67120.6 (3)
C21—C22—C23119.89 (16)C65—C64—C67122.2 (3)
C41—C22—C23118.83 (16)C66—C65—C64119.6 (2)
C24—C23—C18119.40 (16)C66—C65—H65120.2
C24—C23—C22122.16 (15)C64—C65—H65120.2
C18—C23—C22118.44 (16)N61—C66—C65123.2 (2)
C11—C24—C23121.24 (16)N61—C66—H66118.4
C11—C24—H24119.4C65—C66—H66118.4
C23—C24—H24119.4C57—C67—C64115.1 (2)
C32—C31—C12177.2 (2)C57—C67—H67A108.5
C31—C32—I1175.61 (17)C64—C67—H67A108.5
C32—I1—N51175.14 (7)C57—C67—H67B108.5
C42—C41—C22175.9 (2)C64—C67—H67B108.5
C41—C42—I2175.83 (17)H67A—C67—H67B107.5
C56—N51—C52116.38 (18)
C24—C11—C12—C13178.56 (17)C41—C22—C23—C18177.47 (16)
C16—C11—C12—C13−0.9 (3)C16—C11—C24—C23−0.1 (3)
C24—C11—C12—C31−2.9 (3)C12—C11—C24—C23−179.55 (16)
C16—C11—C12—C31177.58 (16)C18—C23—C24—C11−1.1 (3)
C31—C12—C13—C14−178.52 (17)C22—C23—C24—C11178.26 (16)
C11—C12—C13—C140.0 (3)C56—N51—C52—C53−1.1 (3)
C12—C13—C14—C150.8 (3)I1—N51—C52—C53−177.91 (16)
C13—C14—C15—C16−0.6 (3)N51—C52—C53—C540.5 (3)
C14—C15—C16—C17−179.75 (19)C52—C53—C54—C550.8 (3)
C14—C15—C16—C11−0.3 (3)C52—C53—C54—C57179.5 (2)
C24—C11—C16—C171.0 (3)C53—C54—C55—C56−1.5 (3)
C12—C11—C16—C17−179.48 (17)C57—C54—C55—C56179.7 (2)
C24—C11—C16—C15−178.41 (17)C52—N51—C56—C550.3 (3)
C12—C11—C16—C151.1 (3)I1—N51—C56—C55177.58 (16)
C15—C16—C17—C18178.63 (18)C54—C55—C56—N511.0 (3)
C11—C16—C17—C18−0.8 (3)C55—C54—C57—C67134.6 (3)
C16—C17—C18—C19−179.57 (18)C53—C54—C57—C67−44.1 (4)
C16—C17—C18—C23−0.4 (3)C66—N61—C62—C630.4 (3)
C17—C18—C19—C20179.35 (19)I2i—N61—C62—C63−178.46 (17)
C23—C18—C19—C200.1 (3)N61—C62—C63—C64−0.8 (4)
C18—C19—C20—C21−0.8 (3)C62—C63—C64—C650.5 (4)
C19—C20—C21—C220.1 (3)C62—C63—C64—C67179.2 (3)
C20—C21—C22—C41−178.04 (18)C63—C64—C65—C660.1 (4)
C20—C21—C22—C231.3 (3)C67—C64—C65—C66−178.5 (3)
C17—C18—C23—C241.3 (3)C62—N61—C66—C650.3 (3)
C19—C18—C23—C24−179.45 (17)I2i—N61—C66—C65179.28 (18)
C17—C18—C23—C22−178.06 (16)C64—C65—C66—N61−0.5 (4)
C19—C18—C23—C221.2 (3)C54—C57—C67—C64−178.0 (3)
C21—C22—C23—C24178.76 (17)C63—C64—C67—C57119.9 (4)
C41—C22—C23—C24−1.9 (3)C65—C64—C67—C57−61.5 (5)
C21—C22—C23—C18−1.9 (3)
Symmetry code: (i) −x+1, −y+2, −z.
(DIEABpen) TW-10-15 1,8-di(iodoethynyl)anthracene, 1,2-bis(4-pyridyl)ethylene top
Crystal data top
(C18H8I2)(C12H10N2)F(000) = 1272
Mr = 660.26Dx = 1.758 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.4231 (12) ÅCell parameters from 8149 reflections
b = 13.6011 (11) Åθ = 2.2–30.2°
c = 13.4798 (10) ŵ = 2.54 mm−1
β = 109.397 (3)°T = 120 K
V = 2494.2 (3) Å3Plate, yellow
Z = 40.42 × 0.20 × 0.06 mm
Data collection top
Bruker APEX-II CCD
diffractometer		4840 reflections with I > 2σ(I)
φ and ω scansRint = 0.062
Absorption correction: multi-scan
SADABS		θmax = 30.6°, θmin = 2.1°
Tmin = 0.485, Tmax = 0.862h = −20→20
28574 measured reflectionsk = −19→19
7557 independent reflectionsl = −19→19
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.162 w = 1/[σ2(Fo2) + (0.090P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
7557 reflectionsΔρmax = 4.20 e Å−3
307 parametersΔρmin = −1.34 e Å−3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C110.4352 (4)0.3798 (4)0.9798 (4)0.0317 (10)
C120.4634 (3)0.3164 (4)0.9077 (4)0.0308 (10)
C130.5325 (4)0.2456 (4)0.9458 (4)0.0375 (11)
H130.54970.20350.89840.045*
C140.5796 (4)0.2340 (4)1.0564 (4)0.0373 (11)
H140.62770.18411.08180.045*
C150.5564 (4)0.2933 (4)1.1256 (4)0.0351 (11)
H150.58870.28451.19890.042*
C160.4844 (4)0.3682 (4)1.0901 (4)0.0333 (11)
C170.4604 (4)0.4315 (4)1.1594 (4)0.0330 (11)
H170.49440.42551.23280.040*
C180.3884 (4)0.5027 (4)1.1242 (4)0.0320 (10)
C190.3630 (4)0.5666 (4)1.1949 (4)0.0356 (11)
H190.39720.56261.26830.043*
C200.2896 (4)0.6334 (4)1.1568 (4)0.0354 (11)
H200.27210.67391.20520.042*
C210.2384 (4)0.6451 (4)1.0486 (4)0.0390 (12)
H210.18790.69301.02470.047*
C220.2629 (4)0.5854 (4)0.9770 (4)0.0310 (10)
C230.3386 (4)0.5124 (3)1.0133 (4)0.0303 (10)
C240.3645 (3)0.4512 (3)0.9438 (3)0.0287 (10)
H240.33270.45890.87020.034*
C310.4168 (4)0.3305 (4)0.7966 (4)0.0339 (11)
C320.3762 (4)0.3456 (4)0.7040 (4)0.0376 (12)
I10.30702 (3)0.36848 (3)0.54898 (2)0.03563 (12)
C410.2150 (4)0.5969 (4)0.8661 (4)0.0350 (11)
C420.1801 (4)0.6043 (4)0.7715 (4)0.0365 (11)
I20.12471 (3)0.61993 (2)0.61420 (3)0.03521 (12)
N510.2070 (4)0.3868 (3)0.3350 (4)0.0410 (11)
C520.1112 (4)0.4028 (4)0.2926 (4)0.0412 (13)
H520.07490.41700.33830.049*
C530.0612 (4)0.4000 (4)0.1855 (4)0.0378 (12)
H53−0.00760.41150.15900.045*
C540.1135 (4)0.3797 (3)0.1161 (4)0.0288 (10)
C550.2127 (4)0.3621 (4)0.1615 (4)0.0369 (12)
H550.25110.34610.11850.044*
C560.2566 (4)0.3675 (4)0.2692 (4)0.0385 (12)
H560.32540.35690.29810.046*
C570.0598 (4)0.3758 (3)0.0033 (4)0.0337 (11)
H57−0.00940.3849−0.01910.040*
N61−0.0448 (4)0.3520 (3)−0.4024 (4)0.0395 (10)
C620.0518 (4)0.3542 (4)−0.3613 (4)0.0377 (12)
H620.08910.3545−0.40770.045*
C630.1018 (4)0.3561 (4)−0.2540 (4)0.0374 (12)
H630.17160.3577−0.22850.045*
C640.0498 (4)0.3558 (4)−0.1838 (4)0.0329 (11)
C65−0.0532 (4)0.3533 (4)−0.2285 (4)0.0375 (12)
H65−0.09350.3532−0.18520.045*
C66−0.0940 (5)0.3511 (4)−0.3350 (4)0.0451 (14)
H66−0.16360.3487−0.36360.054*
C670.1014 (4)0.3601 (4)−0.0712 (4)0.0349 (11)
H670.17070.3510−0.04810.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.040 (3)0.027 (2)0.027 (2)−0.002 (2)0.0095 (19)−0.0016 (19)
C120.037 (3)0.026 (2)0.028 (2)−0.007 (2)0.0099 (19)0.0009 (19)
C130.049 (3)0.027 (3)0.036 (3)−0.001 (2)0.014 (2)−0.002 (2)
C140.045 (3)0.033 (3)0.033 (3)0.005 (2)0.011 (2)0.007 (2)
C150.042 (3)0.031 (3)0.028 (2)−0.002 (2)0.005 (2)0.003 (2)
C160.037 (3)0.033 (3)0.029 (2)−0.004 (2)0.0102 (19)0.003 (2)
C170.044 (3)0.029 (3)0.024 (2)−0.005 (2)0.010 (2)0.001 (2)
C180.043 (3)0.028 (2)0.024 (2)−0.002 (2)0.0086 (19)−0.0012 (19)
C190.048 (3)0.032 (3)0.025 (2)−0.008 (2)0.009 (2)−0.001 (2)
C200.041 (3)0.033 (3)0.032 (3)−0.006 (2)0.012 (2)−0.005 (2)
C210.046 (3)0.030 (3)0.039 (3)0.000 (2)0.012 (2)−0.004 (2)
C220.043 (3)0.024 (2)0.024 (2)−0.007 (2)0.0082 (19)−0.0014 (19)
C230.040 (3)0.024 (2)0.025 (2)−0.005 (2)0.0079 (19)0.0033 (18)
C240.041 (3)0.024 (2)0.018 (2)−0.004 (2)0.0056 (18)0.0005 (17)
C310.041 (3)0.028 (3)0.032 (3)0.002 (2)0.012 (2)−0.003 (2)
C320.044 (3)0.033 (3)0.037 (3)−0.001 (2)0.015 (2)−0.007 (2)
I10.0478 (2)0.0319 (2)0.02546 (17)0.00177 (14)0.00985 (14)−0.00102 (13)
C410.048 (3)0.022 (2)0.032 (3)−0.004 (2)0.009 (2)−0.003 (2)
C420.042 (3)0.026 (3)0.037 (3)0.000 (2)0.006 (2)−0.001 (2)
I20.0513 (2)0.02436 (18)0.02676 (18)−0.00057 (14)0.00865 (14)0.00173 (12)
N510.060 (3)0.030 (2)0.030 (2)0.001 (2)0.012 (2)0.0016 (19)
C520.056 (3)0.039 (3)0.031 (3)0.006 (3)0.017 (2)−0.002 (2)
C530.042 (3)0.035 (3)0.036 (3)0.002 (2)0.013 (2)0.001 (2)
C540.039 (3)0.021 (2)0.026 (2)−0.0052 (19)0.0100 (19)0.0014 (18)
C550.046 (3)0.034 (3)0.028 (2)0.000 (2)0.010 (2)0.000 (2)
C560.051 (3)0.031 (3)0.030 (3)−0.001 (2)0.007 (2)0.005 (2)
C570.047 (3)0.018 (2)0.030 (2)−0.006 (2)0.005 (2)0.0017 (19)
N610.058 (3)0.027 (2)0.031 (2)−0.004 (2)0.011 (2)−0.0023 (18)
C620.052 (3)0.030 (3)0.030 (3)−0.001 (2)0.013 (2)0.004 (2)
C630.050 (3)0.024 (2)0.036 (3)−0.001 (2)0.012 (2)0.000 (2)
C640.049 (3)0.019 (2)0.029 (2)0.001 (2)0.010 (2)0.0023 (19)
C650.046 (3)0.033 (3)0.032 (3)−0.003 (2)0.011 (2)0.000 (2)
C660.062 (4)0.039 (3)0.034 (3)0.007 (3)0.015 (3)0.001 (2)
C670.042 (3)0.030 (3)0.029 (2)−0.004 (2)0.007 (2)0.003 (2)
Geometric parameters (Å, º) top
C11—C241.375 (7)C41—C421.211 (7)
C11—C161.428 (7)C42—I22.013 (5)
C11—C121.454 (7)I2—N6113.594 (5)
C12—C131.358 (7)N51—C521.326 (7)
C12—C311.437 (7)N51—C561.338 (7)
C13—C141.427 (7)C52—C531.384 (7)
C13—H130.9500C52—H520.9500
C14—C151.357 (7)C53—C541.410 (7)
C14—H140.9500C53—H530.9500
C15—C161.420 (7)C54—C551.378 (7)
C15—H150.9500C54—C571.459 (7)
C16—C171.396 (7)C55—C561.379 (7)
C17—C181.384 (7)C55—H550.9500
C17—H170.9500C56—H560.9500
C18—C191.425 (7)C57—C671.348 (8)
C18—C231.433 (6)C57—H570.9500
C19—C201.360 (7)N61—C621.318 (7)
C19—H190.9500N61—C661.324 (7)
C20—C211.408 (8)C62—C631.386 (7)
C20—H200.9500C62—H620.9500
C21—C221.393 (7)C63—C641.390 (7)
C21—H210.9500C63—H630.9500
C22—C411.432 (7)C64—C651.407 (8)
C22—C231.436 (7)C64—C671.452 (7)
C23—C241.394 (6)C65—C661.359 (8)
C24—H240.9500C65—H650.9500
C31—C321.208 (7)C66—H660.9500
C32—I12.018 (6)C67—H670.9500
I1—N512.775 (5)
C24—C11—C16120.0 (4)C42—C41—C22175.8 (6)
C24—C11—C12121.5 (4)C41—C42—I2178.3 (5)
C16—C11—C12118.5 (5)C42—I2—N61155.36 (15)
C13—C12—C31121.3 (5)C52—N51—C56117.2 (5)
C13—C12—C11120.1 (5)C52—N51—I1124.8 (4)
C31—C12—C11118.7 (4)C56—N51—I1117.6 (4)
C12—C13—C14120.5 (5)N51—C52—C53123.5 (5)
C12—C13—H13119.7N51—C52—H52118.3
C14—C13—H13119.7C53—C52—H52118.3
C15—C14—C13120.8 (5)C52—C53—C54119.3 (5)
C15—C14—H14119.6C52—C53—H53120.3
C13—C14—H14119.6C54—C53—H53120.3
C14—C15—C16120.9 (5)C55—C54—C53116.4 (5)
C14—C15—H15119.5C55—C54—C57124.7 (5)
C16—C15—H15119.5C53—C54—C57118.9 (5)
C17—C16—C15122.2 (5)C54—C55—C56120.3 (5)
C17—C16—C11118.8 (5)C54—C55—H55119.9
C15—C16—C11119.0 (5)C56—C55—H55119.9
C18—C17—C16121.8 (5)N51—C56—C55123.3 (5)
C18—C17—H17119.1N51—C56—H56118.3
C16—C17—H17119.1C55—C56—H56118.3
C17—C18—C19121.8 (5)C67—C57—C54124.7 (5)
C17—C18—C23118.8 (4)C67—C57—H57117.7
C19—C18—C23119.4 (5)C54—C57—H57117.7
C20—C19—C18119.7 (5)C62—N61—C66116.4 (5)
C20—C19—H19120.1C62—N61—I276.1 (3)
C18—C19—H19120.1C66—N61—I243.1 (3)
C19—C20—C21122.8 (5)N61—C62—C63123.3 (5)
C19—C20—H20118.6N61—C62—H62118.3
C21—C20—H20118.6C63—C62—H62118.3
C22—C21—C20119.0 (5)C62—C63—C64120.0 (5)
C22—C21—H21120.5C62—C63—H63120.0
C20—C21—H21120.5C64—C63—H63120.0
C21—C22—C41120.9 (5)C63—C64—C65116.1 (5)
C21—C22—C23120.4 (5)C63—C64—C67120.4 (5)
C41—C22—C23118.6 (4)C65—C64—C67123.5 (5)
C24—C23—C18119.5 (4)C66—C65—C64118.5 (5)
C24—C23—C22121.8 (4)C66—C65—H65120.7
C18—C23—C22118.7 (4)C64—C65—H65120.7
C11—C24—C23121.2 (4)N61—C66—C65125.6 (6)
C11—C24—H24119.4N61—C66—H66117.2
C23—C24—H24119.4C65—C66—H66117.2
C32—C31—C12177.6 (6)C57—C67—C64125.7 (5)
C31—C32—I1178.9 (5)C57—C67—H67117.1
C32—I1—N51176.07 (18)C64—C67—H67117.1
C24—C11—C12—C13−179.1 (5)C41—C22—C23—C18178.3 (4)
C16—C11—C12—C132.4 (7)C16—C11—C24—C23−0.8 (7)
C24—C11—C12—C311.0 (7)C12—C11—C24—C23−179.3 (4)
C16—C11—C12—C31−177.6 (5)C18—C23—C24—C111.7 (7)
C31—C12—C13—C14178.7 (5)C22—C23—C24—C11−178.1 (5)
C11—C12—C13—C14−1.3 (8)C56—N51—C52—C530.3 (8)
C12—C13—C14—C15−0.1 (8)I1—N51—C52—C53−172.0 (4)
C13—C14—C15—C160.3 (8)N51—C52—C53—C54−0.4 (9)
C14—C15—C16—C17−178.8 (5)C52—C53—C54—C551.2 (7)
C14—C15—C16—C110.9 (8)C52—C53—C54—C57179.3 (5)
C24—C11—C16—C17−1.1 (7)C53—C54—C55—C56−1.9 (7)
C12—C11—C16—C17177.5 (5)C57—C54—C55—C56−179.9 (5)
C24—C11—C16—C15179.3 (5)C52—N51—C56—C55−1.1 (8)
C12—C11—C16—C15−2.2 (7)I1—N51—C56—C55171.8 (4)
C15—C16—C17—C18−178.3 (5)C54—C55—C56—N511.9 (8)
C11—C16—C17—C182.0 (8)C55—C54—C57—C67−4.1 (8)
C16—C17—C18—C19179.3 (5)C53—C54—C57—C67177.9 (5)
C16—C17—C18—C23−1.1 (7)C66—N61—C62—C63−0.4 (8)
C17—C18—C19—C20−177.9 (5)I2—N61—C62—C6315.3 (4)
C23—C18—C19—C202.4 (7)N61—C62—C63—C640.0 (8)
C18—C19—C20—C21−2.1 (8)C62—C63—C64—C650.1 (7)
C19—C20—C21—C220.6 (8)C62—C63—C64—C67−178.6 (5)
C20—C21—C22—C41−177.9 (5)C63—C64—C65—C660.2 (7)
C20—C21—C22—C230.5 (8)C67—C64—C65—C66178.9 (5)
C17—C18—C23—C24−0.8 (7)C62—N61—C66—C650.7 (9)
C19—C18—C23—C24178.9 (5)I2—N61—C66—C65−21.8 (4)
C17—C18—C23—C22179.1 (4)C64—C65—C66—N61−0.7 (9)
C19—C18—C23—C22−1.3 (7)C54—C57—C67—C64180.0 (4)
C21—C22—C23—C24179.7 (5)C63—C64—C67—C57168.9 (5)
C41—C22—C23—C24−1.9 (7)C65—C64—C67—C57−9.7 (8)
C21—C22—C23—C18−0.2 (7)
 

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