Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 5| May 2014| Pages o625-o626
doi:10.1107/S1600536814009362

Four-layered [3.3]meta­cyclo­phane with ethene­tetra­carbo­nitrile

Masahiko Shibahara,a* Motonori Watanabe,b Kenta Gotoc and Teruo Shinmyozuc

aDepartment of Chemistry, Faculty of Education and Welfare Science, Oita University, 700 Dannoharu, Oita 870-1192, Japan, bInternational Institute for Carbon-Neutral Energy Research (I2CNER), Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan, and cInstitute for Materials Chemistry and Engineering (IMCE), Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan
*Correspondence e-mail: mshiba@oita-u.ac.jp

(Received 1 March 2014; accepted 25 April 2014; online 30 April 2014)

The title complex C42H48·2C6N4 {systematic name: hepta­cyclo[21.13.1.15,19.16,18.110,14.124,36.128,32]do­tetra­conta-1(37),5(40),6(41),10(42),11,13,18,23,28,30,32(39),36(38)-dodeca­ene–ethene­tetra­carbo­nitrile (1/2)}, consisting of four-layered [3.3]meta­cyclo­phane (MCP) with two tetra­cyano­ethyl­ene (TCNE) mol­ecules, was grown from a mixture of MCP and TCNE in chloro­form solution. The four-layered [3.3]MCP has an S-shaped structure in which three [3.3]MCP moieties take syn-(chair-boat), anti-(chair-boat) and syn-(chair-boat) conformations. The two outer [3.3]MCP moieties with syn geometry contain benzene rings with a tilt of 32.95 (7)°. The central [3.3]MCP moiety has an anti geometry, in which the two benzene rings are oriented parallel to each other at a transannular distance of 2.31 Å. The TCNE mol­ecules are stacked on either side of the outer [3.3]MCP units at a distance of 3.19 Å on one side and 3.24 Å on the other, and showed 0.80:0.20 and 0.44:0.56 disorder, respectively.

CCDC reference: 999480

Related literature

For the previously reported C42H48·C6N4 (1:1) complex, see: Shibahara et al. (2011a[Shibahara, M., Watanabe, M., Chan, Y., Goto, K. & Shinmyozu, T. (2011a). Tetrahedron Lett. 52, 3371-3375.]). For the free ligand C42H48, see: Shibahara et al. (2007[Shibahara, M., Watanabe, M., Iwanaga, T., Ideta, K. & Shinmyozu, T. (2007). J. Org. Chem. 72, 2865-2877.]). For multilayered [3.3]para­cyclo­phanes, see: Shibahara et al. (2008[Shibahara, M., Watanabe, M., Iwanaga, T., Matsumoto, T., Ideta, K. & Shinmyozu, T. (2008). J. Org. Chem. 73, 4433-4442.], 2011a[Shibahara, M., Watanabe, M., Chan, Y., Goto, K. & Shinmyozu, T. (2011a). Tetrahedron Lett. 52, 3371-3375.],b[Shibahara, M., Watanabe, M., Chan, Y. & Shinmyozu, T. (2011b). Tetrahedron Lett. 52, 5012-5015.]). For cyclo­phanes, see: Vögtle (1993[Vögtle, F. (1993). In Cyclophane Chemistry. England: John Wiley & Sons Ltd.]).

[Scheme 1]

Experimental

Crystal data

  • C42H48·2C6N4

  • Mr = 809.03

  • Triclinic, [P \overline 1]

  • a = 9.563 (3) Å

  • b = 10.101 (4) Å

  • c = 11.679 (4) Å

  • α = 96.365 (14)°

  • β = 99.134 (13)°

  • γ = 107.683 (13)°

  • V = 1045.9 (6) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 123 K

  • 0.35 × 0.16 × 0.09 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • 17470 measured reflections

  • 4775 independent reflections

  • 4141 reflections with F2 > 2σ(F2)

  • Rint = 0.050
Refinement

  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.178

  • S = 1.00

  • 4775 reflections

  • 394 parameters

  • Only H-atom coordinates refined

  • Δρmax = 0.80 e Å−3

  • Δρmin = −0.50 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXD (Schneider & Sheldrick, 2002[Schneider, T. R. & Sheldrick, G. M. (2002). Acta Cryst. D58, 1772-1779.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku, Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.

Supporting information

CCDC reference: 999480

Crystal structure: contains datablocks General, I. DOI: 10.1107/S1600536814009362/gw2145sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814009362/gw2145Isup2.hkl

checkCIF report


Comment top

The title complex consists of four-layered [3.3]metacyclophane (MCP) with two tetracyanoethylene molecules (TCNE). The TCNE molecules are stacked on either side of the outer [3.3]MCP units at a distance of 3.19 Å on one side and 3.24 Å on the other, and showed 0.80:0.20 and 0.44:0.56 disorder, respectively.

Related literature top

For the previously reported C42H48.C6N4 (1:1) complex, see: Shibahara et al. (2011b). For the free ligand C42H48, see: Shibahara et al. (2007). For multilayered [3.3]paracyclophanes, see: Shibahara et al. (2008, 2011a,b). For cyclophanes, see: Vögtle (1993).

Experimental top

The complex of single-crystal C42H48.2C6N4, consisting of four-layered [3.3]metacyclophane (MCP) with two tetracyanoethylene (TCNE) molecules, was synthesized. The black block crystals were obtained by slow diffusion from 2 mM of four-layered [3.3]MCP with 20 mM of TCNE in chloroform solution.

Refinement top

All the hydrogen atoms of the compound are fixed geometrically (C—H = 0.93–0.97 Å) and allowed to ride on their parent atoms. Structure was refined with unique reflections and with a cut-off sigma = 2.00.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: RAPID-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXD (Schneider & Sheldrick, 2002); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of C42H48.2C6N4 with the atom-labelling scheme and displacement ellipsoids are drawn at the 50% probability level. H atoms are omitted for clarity.
[Figure 2] Fig. 2. A packing diagram of C42H48.2C6N4.
Heptacyclo[21.13.1.15,19.16,18.110,14.124,36.128,32]dotetraconta-1(37),5(40),6(41),10 (42),11,13,18,23,28,30,32 (39),36 (38)-dodecaene–ethenetetracarbonitrile (1/2) top
Crystal data top
C42H48·2C6N4Z = 1
Mr = 809.03F(000) = 428.00
Triclinic, P1Dx = 1.284 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 9.563 (3) ÅCell parameters from 13845 reflections
b = 10.101 (4) Åθ = 3.0–27.5°
c = 11.679 (4) ŵ = 0.08 mm−1
α = 96.365 (14)°T = 123 K
β = 99.134 (13)°Block, black
γ = 107.683 (13)°0.35 × 0.16 × 0.09 mm
V = 1045.9 (6) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer		Rint = 0.050
ω/2θ scansθmax = 27.5°
17470 measured reflectionsh = −12→11
4775 independent reflectionsk = −13→13
4141 reflections with F2 > 2σ(F2)l = −15→15
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178Only H-atom coordinates refined
S = 1.00 w = 1/[σ2(Fo2) + (0.1296P)2 + 0.1947P]
where P = (Fo2 + 2Fc2)/3
4775 reflections(Δ/σ)max < 0.001
394 parametersΔρmax = 0.80 e Å−3
0 restraintsΔρmin = −0.50 e Å−3
Primary atom site location: structure-invariant direct methods
Crystal data top
C42H48·2C6N4γ = 107.683 (13)°
Mr = 809.03V = 1045.9 (6) Å3
Triclinic, P1Z = 1
a = 9.563 (3) ÅMo Kα radiation
b = 10.101 (4) ŵ = 0.08 mm−1
c = 11.679 (4) ÅT = 123 K
α = 96.365 (14)°0.35 × 0.16 × 0.09 mm
β = 99.134 (13)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		4141 reflections with F2 > 2σ(F2)
17470 measured reflectionsRint = 0.050
4775 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.178Only H-atom coordinates refined
S = 1.00Δρmax = 0.80 e Å−3
4775 reflectionsΔρmin = −0.50 e Å−3
394 parameters
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.30526 (16)0.71021 (14)0.53324 (14)0.0447 (4)
N2−0.13890 (17)0.62272 (16)0.31010 (12)0.0437 (4)
N30.70465 (15)0.29951 (14)0.04664 (13)0.0426 (4)
N40.63339 (18)−0.04481 (19)0.23634 (12)0.0507 (4)
C10.27496 (16)0.35932 (14)0.38821 (12)0.0292 (3)
C20.17966 (15)0.23727 (14)0.41376 (11)0.0271 (3)
C30.02899 (16)0.18988 (15)0.35613 (12)0.0308 (3)
C4−0.02123 (17)0.26252 (16)0.27325 (13)0.0344 (4)
C50.07747 (18)0.38055 (16)0.24516 (12)0.0344 (4)
C60.22797 (17)0.42945 (14)0.30050 (13)0.0314 (4)
C70.3425 (3)0.54751 (16)0.26353 (17)0.0421 (4)
C80.46096 (18)0.50271 (16)0.21084 (14)0.0379 (4)
C90.40369 (16)0.39146 (14)0.10058 (13)0.0306 (3)
C100.33220 (14)0.23804 (13)0.11189 (12)0.0247 (3)
C110.22263 (14)0.14374 (13)0.01981 (11)0.0232 (3)
C120.16183 (14)0.00361 (13)0.03416 (11)0.0237 (3)
C130.19319 (14)−0.04508 (13)0.13956 (11)0.0232 (3)
C140.30253 (14)0.04905 (13)0.23209 (11)0.0235 (3)
C150.37473 (14)0.18541 (13)0.21330 (12)0.0251 (3)
C160.34394 (15)0.00796 (14)0.35098 (12)0.0271 (3)
C170.23470 (17)0.00835 (14)0.43550 (12)0.0309 (3)
C180.23976 (18)0.15347 (15)0.49632 (12)0.0332 (4)
C190.15916 (14)0.18891 (14)−0.09117 (11)0.0248 (3)
C200.11033 (14)−0.19487 (13)0.15283 (12)0.0253 (3)
C21−0.04379 (14)−0.26541 (13)0.07162 (11)0.0240 (3)
C220.0677 (9)0.5125 (7)0.5331 (7)0.0274 (14)0.2000
C230.0276 (2)0.55598 (17)0.47359 (15)0.0251 (4)0.8000
C240.18542 (17)0.63929 (15)0.51109 (13)0.0343 (4)
C25−0.07150 (17)0.58885 (15)0.38230 (12)0.0332 (4)
C260.5541 (3)0.0410 (3)0.0464 (3)0.0283 (5)0.5600
C270.4895 (4)−0.0541 (4)0.0308 (3)0.0263 (6)0.4400
C280.62892 (17)0.18694 (17)0.03210 (17)0.0426 (4)
C290.58456 (17)−0.02573 (17)0.14916 (13)0.0354 (4)
H10.383 (2)0.3942 (18)0.4314 (15)0.033 (5)*
H2−0.045 (3)0.101 (3)0.3716 (17)0.049 (6)*
H3−0.131 (3)0.228 (2)0.2321 (16)0.041 (5)*
H40.041 (3)0.428 (3)0.1855 (19)0.050 (6)*
H50.297 (3)0.587 (3)0.205 (3)0.081 (8)*
H60.390 (3)0.626 (3)0.327 (2)0.058 (6)*
H70.534 (3)0.588 (3)0.1889 (17)0.051 (6)*
H80.530 (3)0.469 (2)0.2774 (17)0.042 (5)*
H90.322 (3)0.419 (3)0.0470 (18)0.051 (6)*
H100.488 (2)0.3976 (19)0.0554 (16)0.043 (5)*
H110.0882 (17)−0.0620 (16)−0.0336 (14)0.021 (4)*
H120.4578 (18)0.2534 (17)0.2809 (14)0.027 (4)*
H130.452 (2)0.0727 (18)0.3944 (15)0.033 (5)*
H140.3556 (17)−0.0871 (17)0.3366 (13)0.024 (4)*
H150.260 (2)−0.0488 (19)0.4963 (16)0.038 (5)*
H160.125 (2)−0.0487 (19)0.3960 (16)0.037 (5)*
H170.179 (3)0.138 (2)0.5597 (18)0.048 (5)*
H180.352 (3)0.212 (3)0.5384 (18)0.050 (6)*
H190.1086 (18)0.0987 (18)−0.1549 (14)0.029 (4)*
H200.242 (2)0.2516 (18)−0.1231 (15)0.034 (5)*
H210.0979 (19)−0.1933 (17)0.2372 (14)0.029 (4)*
H220.1777 (19)−0.2508 (18)0.1392 (15)0.035 (5)*
H23−0.0359 (18)−0.2743 (17)−0.0123 (15)0.029 (4)*
H24−0.0813 (19)−0.3631 (18)0.0886 (14)0.028 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0341 (8)0.0348 (7)0.0587 (9)0.0038 (6)0.0098 (6)0.0017 (6)
N20.0523 (9)0.0596 (9)0.0346 (7)0.0334 (7)0.0143 (6)0.0209 (7)
N30.0335 (7)0.0360 (7)0.0599 (9)0.0112 (6)0.0152 (6)0.0066 (6)
N40.0539 (9)0.0834 (12)0.0354 (8)0.0470 (9)0.0129 (7)0.0190 (7)
C10.0316 (8)0.0267 (7)0.0322 (7)0.0119 (6)0.0093 (6)0.0056 (6)
C20.0324 (7)0.0262 (7)0.0252 (7)0.0116 (6)0.0086 (5)0.0048 (5)
C30.0321 (8)0.0283 (7)0.0326 (7)0.0101 (6)0.0100 (6)0.0023 (6)
C40.0354 (8)0.0381 (8)0.0310 (7)0.0181 (6)0.0033 (6)−0.0021 (6)
C50.0500 (9)0.0357 (8)0.0272 (7)0.0266 (7)0.0097 (6)0.0064 (6)
C60.0422 (8)0.0266 (7)0.0336 (7)0.0178 (6)0.0160 (6)0.0077 (6)
C70.0601 (11)0.0261 (7)0.0492 (10)0.0170 (7)0.0262 (8)0.0138 (7)
C80.0360 (8)0.0302 (7)0.0450 (9)0.0051 (6)0.0083 (7)0.0134 (7)
C90.0333 (8)0.0256 (7)0.0385 (8)0.0108 (6)0.0145 (6)0.0144 (6)
C100.0235 (7)0.0250 (6)0.0318 (7)0.0118 (5)0.0111 (5)0.0119 (5)
C110.0222 (6)0.0262 (6)0.0288 (7)0.0136 (5)0.0102 (5)0.0121 (5)
C120.0211 (6)0.0263 (7)0.0285 (7)0.0113 (5)0.0080 (5)0.0104 (5)
C130.0214 (6)0.0251 (6)0.0294 (7)0.0124 (5)0.0087 (5)0.0111 (5)
C140.0219 (6)0.0265 (6)0.0279 (7)0.0130 (5)0.0081 (5)0.0104 (5)
C150.0235 (7)0.0260 (7)0.0296 (7)0.0110 (5)0.0079 (5)0.0088 (5)
C160.0282 (7)0.0271 (7)0.0285 (7)0.0115 (5)0.0043 (5)0.0104 (5)
C170.0395 (8)0.0282 (7)0.0295 (7)0.0137 (6)0.0098 (6)0.0119 (6)
C180.0447 (9)0.0305 (7)0.0274 (7)0.0153 (6)0.0073 (6)0.0088 (6)
C190.0249 (7)0.0279 (7)0.0275 (7)0.0125 (5)0.0087 (5)0.0126 (5)
C200.0249 (7)0.0249 (6)0.0308 (7)0.0115 (5)0.0073 (5)0.0126 (5)
C210.0266 (7)0.0223 (6)0.0268 (7)0.0113 (5)0.0065 (5)0.0086 (5)
C220.040 (5)0.017 (3)0.031 (4)0.010 (4)0.019 (3)0.012 (3)
C230.0266 (10)0.0231 (8)0.0266 (9)0.0084 (8)0.0064 (7)0.0061 (7)
C240.0343 (8)0.0280 (7)0.0386 (8)0.0063 (6)0.0121 (6)0.0022 (6)
C250.0437 (9)0.0334 (7)0.0293 (7)0.0195 (6)0.0101 (6)0.0101 (6)
C260.0248 (12)0.0312 (16)0.0336 (16)0.0135 (12)0.0075 (11)0.0101 (11)
C270.0206 (14)0.0318 (19)0.0283 (17)0.0114 (14)0.0046 (12)0.0046 (14)
C280.0300 (8)0.0343 (8)0.0663 (11)0.0112 (7)0.0186 (7)0.0048 (8)
C290.0316 (8)0.0508 (9)0.0325 (8)0.0241 (7)0.0081 (6)0.0110 (7)
Geometric parameters (Å, º) top
N1—C241.1223 (19)C23—C251.447 (3)
N2—C251.126 (3)C26—C26iii1.362 (4)
N3—C281.124 (2)C26—C27iii0.972 (5)
N4—C291.113 (3)C26—C281.472 (4)
C1—C21.3873 (19)C26—C291.472 (4)
C1—C61.400 (3)C27—C27iii1.356 (6)
C2—C31.4000 (19)C27—C28iii1.488 (4)
C2—C181.509 (3)C27—C291.475 (4)
C3—C41.389 (3)C1—H11.007 (17)
C4—C51.386 (3)C3—H21.01 (2)
C5—C61.391 (3)C4—H31.015 (19)
C6—C71.510 (3)C5—H40.97 (3)
C7—C81.529 (3)C7—H50.95 (3)
C8—C91.517 (2)C7—H60.96 (2)
C9—C101.5221 (19)C8—H71.02 (2)
C10—C111.4037 (16)C8—H81.09 (2)
C10—C151.403 (2)C9—H91.05 (3)
C11—C121.3975 (19)C9—H101.02 (2)
C11—C191.519 (2)C12—H110.992 (13)
C12—C131.398 (2)C15—H121.037 (14)
C13—C141.4052 (16)C16—H131.047 (15)
C13—C201.5178 (18)C16—H140.999 (18)
C14—C151.3997 (18)C17—H151.01 (2)
C14—C161.520 (2)C17—H161.029 (17)
C16—C171.547 (3)C18—H171.01 (3)
C17—C181.540 (3)C18—H181.060 (19)
C19—C21i1.557 (3)C19—H191.042 (15)
C20—C211.5323 (17)C19—H201.006 (18)
C22—C22ii1.333 (11)C20—H211.010 (18)
C22—C241.504 (7)C20—H221.00 (2)
C22—C25ii1.504 (8)C21—H230.991 (18)
C23—C23ii1.354 (3)C21—H240.996 (18)
C23—C241.454 (3)
N1···C22ii3.499 (8)C20···H142.762 (14)
N1···C23ii3.470 (3)C20···H163.013 (18)
N1···C253.523 (3)C20···H19i2.56 (2)
N1···C25ii3.515 (3)C20···H20i3.198 (19)
N2···C223.503 (8)C21···H4i3.27 (3)
N2···C23ii3.478 (3)C21···H9i2.697 (19)
N2···C243.528 (3)C21···H112.608 (16)
N2···C24ii3.517 (3)C21···H11i3.526 (18)
N3···C26iii3.504 (3)H1···H53.59 (4)
N3···C273.506 (4)H1···H62.74 (4)
N3···C293.544 (3)H1···H82.50 (3)
N3···C29iii3.531 (2)H1···H122.47 (3)
N4···C26iii3.509 (4)H1···H133.50 (3)
N4···C27iii3.514 (4)H1···H173.39 (3)
N4···C283.527 (3)H1···H182.31 (3)
N4···C28iii3.535 (3)H2···H32.38 (3)
C1···C42.757 (2)H2···H162.54 (4)
C1···C83.134 (3)H2···H172.72 (3)
C1···C103.508 (3)H2···H19i2.91 (3)
C1···C143.550 (3)H3···H42.36 (3)
C1···C153.002 (3)H3···H11i2.86 (3)
C1···C173.563 (3)H3···H19i3.40 (3)
C2···C52.794 (3)H3···H23i3.23 (3)
C2···C143.279 (3)H4···H52.44 (3)
C2···C153.308 (3)H4···H63.37 (3)
C2···C163.251 (3)H4···H93.37 (4)
C3···C62.800 (2)H4···H23i2.39 (3)
C3···C173.175 (3)H4···H24i3.30 (3)
C5···C83.600 (3)H5···H72.30 (4)
C6···C93.140 (3)H5···H82.89 (4)
C6···C103.241 (3)H5···H92.45 (4)
C6···C153.329 (3)H5···H103.53 (4)
C7···C103.383 (3)H6···H72.35 (4)
C8···C153.062 (3)H6···H82.44 (4)
C9···C193.0140 (18)H6···H93.53 (3)
C9···C21i3.476 (2)H7···H92.44 (3)
C10···C132.843 (2)H7···H102.22 (3)
C10···C21i3.316 (2)H7···H123.56 (3)
C11···C12i3.444 (2)H8···H92.97 (3)
C11···C142.831 (2)H8···H102.55 (3)
C12···C12i3.048 (2)H8···H122.09 (3)
C12···C152.7237 (17)H9···H202.32 (3)
C12···C19i3.310 (2)H9···H23i2.63 (3)
C12···C212.9550 (19)H9···H24i2.45 (3)
C12···C21i3.448 (3)H10···H123.16 (3)
C13···C173.379 (3)H10···H202.78 (3)
C13···C19i3.1660 (19)H11···H11i2.55 (3)
C14···C183.354 (3)H11···H192.26 (3)
C15···C173.522 (3)H11···H19i3.10 (3)
C16···C203.0117 (18)H11···H203.42 (3)
C17···C203.506 (2)H11···H213.56 (3)
N1···C63.515 (3)H11···H223.12 (3)
N1···C73.509 (3)H11···H232.18 (3)
N1···C17iv3.547 (3)H11···H23i3.58 (3)
N2···C2ii3.504 (3)H11···H243.55 (3)
N2···C8v3.594 (3)H12···H132.36 (3)
N2···C18ii3.469 (3)H12···H143.44 (3)
N2···C19vi3.368 (3)H12···H183.35 (3)
N2···C20iv3.453 (3)H13···H152.43 (3)
N2···C21iv3.277 (3)H13···H162.99 (3)
N3···C4vii3.553 (3)H13···H182.55 (3)
N3···C93.408 (3)H14···H152.25 (3)
N3···C20iii3.402 (3)H14···H162.53 (3)
N4···C143.563 (3)H14···H212.40 (2)
N4···C163.414 (3)H14···H222.67 (2)
N4···C18viii3.576 (3)H15···H172.33 (4)
N4···C19iii3.347 (3)H15···H182.48 (3)
C1···C223.396 (9)H15···H213.14 (3)
C1···C243.428 (3)H16···H172.40 (3)
C2···N2ii3.504 (3)H16···H182.97 (3)
C2···C223.499 (9)H16···H19i3.19 (3)
C2···C23ii3.571 (3)H16···H212.16 (3)
C2···C25ii3.284 (3)H19···H21i2.55 (3)
C3···C223.544 (8)H19···H22i3.54 (3)
C3···C22ii3.573 (9)H19···H23i2.80 (3)
C3···C23ii3.300 (3)H19···H24i2.80 (3)
C3···C24ii3.486 (3)H20···H21i3.16 (3)
C3···C25ii3.469 (3)H20···H23i2.76 (3)
C4···N3v3.553 (3)H20···H24i2.22 (3)
C4···C223.534 (7)H21···H232.91 (3)
C4···C22ii3.204 (8)H21···H242.346 (19)
C4···C233.428 (3)H22···H232.41 (3)
C4···C23ii3.321 (3)H22···H242.33 (3)
C4···C24ii3.382 (3)N1···H1x3.44 (2)
C4···C253.598 (3)N1···H3ii3.52 (3)
C5···C223.504 (8)N1···H62.79 (3)
C5···C22ii3.351 (9)N1···H8x3.49 (3)
C5···C233.218 (3)N1···H12x2.781 (16)
C5···C253.289 (3)N1···H13x2.607 (15)
C6···N13.515 (3)N1···H14iv3.239 (17)
C6···C223.468 (9)N1···H15iv2.67 (2)
C6···C233.397 (3)N1···H18x3.39 (3)
C6···C243.224 (3)N2···H43.34 (3)
C7···N13.509 (3)N2···H7v3.12 (2)
C8···N2vii3.594 (3)N2···H8v3.010 (19)
C9···N33.408 (3)N2···H16iv3.431 (16)
C9···C283.526 (3)N2···H17ii2.87 (3)
C10···C263.434 (4)N2···H18ii3.55 (3)
C10···C27iii3.358 (5)N2···H19vi3.477 (18)
C10···C283.288 (3)N2···H20vi2.838 (19)
C11···C26iii3.356 (4)N2···H21iv2.777 (17)
C11···C27iii3.265 (5)N2···H24iv2.740 (17)
C11···C29iii3.269 (3)N3···H3vii2.76 (2)
C12···C26iii3.151 (4)N3···H4vii3.16 (2)
C12···C273.362 (5)N3···H5xi3.27 (3)
C12···C27iii3.436 (4)N3···H9xi3.22 (3)
C12···C28iii3.288 (3)N3···H102.56 (3)
C12···C29iii3.456 (3)N3···H11iii3.550 (19)
C13···C26iii3.491 (4)N3···H22iii2.663 (19)
C13···C273.305 (4)N3···H23iii3.336 (19)
C13···C28iii3.300 (3)N3···H24xii3.334 (16)
C14···N43.563 (3)N4···H2vii3.055 (19)
C14···C263.497 (4)N4···H3vii2.996 (18)
C14···C273.426 (5)N4···H7ix3.49 (2)
C14···C293.269 (3)N4···H133.10 (2)
C15···C263.289 (4)N4···H143.003 (17)
C15···C273.580 (5)N4···H15viii3.071 (17)
C15···C27iii3.599 (4)N4···H17viii3.15 (3)
C15···C283.465 (3)N4···H18viii3.29 (3)
C15···C293.444 (3)N4···H19iii2.955 (19)
C16···N43.414 (3)N4···H20iii2.99 (2)
C17···N1ix3.547 (3)C3···H15xiii3.508 (19)
C18···N2ii3.469 (3)C7···H18x3.476 (17)
C18···N4viii3.576 (3)C7···H22iv3.26 (2)
C19···N2vi3.368 (3)C8···H10xi3.435 (19)
C19···N4iii3.347 (3)C8···H20xi3.532 (18)
C19···C29iii3.452 (3)C9···H7xi3.54 (2)
C20···N2ix3.453 (3)C9···H9xi3.55 (3)
C20···N3iii3.402 (3)C9···H10xi3.008 (19)
C20···C28iii3.538 (3)C17···H2xiii3.20 (3)
C21···N2ix3.277 (3)C18···H2xiii3.37 (2)
C22···C13.396 (9)C19···H7xi3.55 (2)
C22···C23.499 (9)C20···H5ix3.28 (4)
C22···C33.544 (8)C22···H3ii3.42 (2)
C22···C3ii3.573 (9)C23···H43.50 (3)
C22···C43.534 (7)C24···H2ii3.53 (3)
C22···C4ii3.204 (8)C24···H3ii3.33 (2)
C22···C53.504 (8)C24···H63.15 (3)
C22···C5ii3.351 (9)C24···H15iv3.043 (19)
C22···C63.468 (9)C25···H43.18 (3)
C23···C2ii3.571 (3)C25···H8v3.586 (19)
C23···C3ii3.300 (3)C25···H16iv3.544 (18)
C23···C43.428 (3)C25···H17ii3.27 (3)
C23···C4ii3.321 (3)C25···H21iv3.142 (17)
C23···C53.218 (3)C25···H24iv3.508 (17)
C23···C63.397 (3)C26···H3vii3.304 (17)
C24···C13.428 (3)C26···H11iii3.391 (18)
C24···C3ii3.486 (3)C27···H10iii3.58 (2)
C24···C4ii3.382 (3)C27···H223.549 (18)
C24···C63.224 (3)C28···H3vii2.900 (19)
C25···C2ii3.284 (3)C28···H102.85 (3)
C25···C3ii3.469 (3)C28···H11iii3.313 (19)
C25···C43.598 (3)C28···H22iii2.927 (19)
C25···C53.289 (3)C29···H3vii3.049 (17)
C26···C103.434 (4)C29···H11iii3.510 (17)
C26···C11iii3.356 (4)C29···H133.479 (19)
C26···C12iii3.151 (4)C29···H143.312 (17)
C26···C13iii3.491 (4)C29···H19iii3.228 (19)
C26···C143.497 (4)C29···H20iii3.22 (3)
C26···C153.289 (4)H1···N1x3.44 (2)
C27···C10iii3.358 (5)H1···H1x2.71 (2)
C27···C11iii3.265 (5)H1···H6x3.34 (3)
C27···C123.362 (5)H1···H8x3.39 (3)
C27···C12iii3.436 (4)H2···N4v3.055 (19)
C27···C133.305 (4)H2···C17xiii3.20 (3)
C27···C143.426 (5)H2···C18xiii3.37 (2)
C27···C153.580 (5)H2···C24ii3.53 (3)
C27···C15iii3.599 (4)H2···H15xiii2.73 (3)
C28···C93.526 (3)H2···H16xiii3.00 (3)
C28···C103.288 (3)H2···H17xiii2.65 (3)
C28···C12iii3.288 (3)H3···N1ii3.52 (3)
C28···C13iii3.300 (3)H3···N3v2.76 (2)
C28···C153.465 (3)H3···N4v2.996 (18)
C28···C20iii3.538 (3)H3···C22ii3.42 (2)
C29···C11iii3.269 (3)H3···C24ii3.33 (2)
C29···C12iii3.456 (3)H3···C26v3.304 (17)
C29···C143.269 (3)H3···C28v2.900 (19)
C29···C153.444 (3)H3···C29v3.049 (17)
C29···C19iii3.452 (3)H4···N23.34 (3)
C1···H23.321 (19)H4···N3v3.16 (2)
C1···H43.27 (3)H4···C233.50 (3)
C1···H53.30 (3)H4···C253.18 (3)
C1···H62.80 (3)H4···H22iv3.25 (3)
C1···H82.92 (2)H4···H24iv2.95 (4)
C1···H122.70 (2)H5···N3xi3.27 (3)
C1···H173.19 (3)H5···C20iv3.28 (4)
C1···H182.58 (3)H5···H14iv3.32 (4)
C2···H33.33 (2)H5···H21iv3.36 (4)
C2···H123.257 (19)H5···H22iv2.39 (4)
C2···H133.51 (2)H6···N12.79 (3)
C2···H153.41 (2)H6···C243.15 (3)
C2···H162.75 (2)H6···H1x3.34 (3)
C3···H13.299 (16)H6···H14iv3.01 (4)
C3···H43.28 (3)H6···H18x2.64 (3)
C3···H162.89 (3)H6···H22iv3.35 (4)
C3···H172.77 (2)H7···N2vii3.12 (2)
C3···H183.39 (2)H7···N4iv3.49 (2)
C3···H19i3.304 (15)H7···C9xi3.54 (2)
C4···H11i3.119 (15)H7···C19xi3.55 (2)
C4···H19i3.547 (17)H7···H9xi3.27 (4)
C4···H23i3.189 (18)H7···H10xi2.85 (3)
C5···H13.308 (18)H7···H18x3.40 (3)
C5···H23.31 (2)H7···H20xi2.55 (3)
C5···H52.62 (3)H8···N1x3.49 (3)
C5···H63.17 (2)H8···N2vii3.010 (19)
C5···H93.52 (3)H8···C25vii3.586 (19)
C5···H11i3.587 (14)H8···H1x3.39 (3)
C5···H23i2.731 (17)H8···H18x3.42 (3)
C6···H33.327 (18)H9···N3xi3.22 (3)
C6···H73.41 (2)H9···C9xi3.55 (3)
C6···H82.86 (2)H9···H7xi3.27 (4)
C6···H93.23 (3)H9···H10xi2.70 (3)
C6···H123.24 (2)H10···N32.56 (3)
C6···H23i3.504 (15)H10···C8xi3.435 (19)
C7···H12.681 (19)H10···C9xi3.008 (19)
C7···H42.72 (2)H10···C27iii3.58 (2)
C7···H92.66 (2)H10···C282.85 (3)
C7···H103.42 (2)H10···H7xi2.85 (3)
C7···H123.484 (19)H10···H9xi2.70 (3)
C8···H13.023 (19)H10···H10xi2.53 (3)
C8···H122.726 (18)H11···N3iii3.550 (19)
C9···H52.74 (3)H11···C26iii3.391 (18)
C9···H63.39 (3)H11···C28iii3.313 (19)
C9···H122.719 (18)H11···C29iii3.510 (17)
C9···H202.789 (15)H12···N1x2.781 (16)
C9···H23i3.299 (16)H13···N1x2.607 (15)
C9···H24i3.410 (17)H13···N43.10 (2)
C10···H73.411 (19)H13···C293.479 (19)
C10···H82.817 (16)H13···H13viii3.16 (3)
C10···H113.289 (13)H13···H14viii3.34 (3)
C10···H193.368 (15)H13···H15viii2.94 (3)
C10···H202.773 (18)H14···N1ix3.239 (17)
C10···H23i3.033 (18)H14···N43.003 (17)
C11···H92.62 (2)H14···C293.312 (17)
C11···H102.944 (17)H14···H5ix3.32 (4)
C11···H11i2.870 (16)H14···H6ix3.01 (4)
C11···H123.338 (15)H14···H13viii3.34 (3)
C11···H23i2.52 (2)H14···H18viii3.58 (3)
C11···H24i3.20 (2)H15···N1ix2.67 (2)
C12···H3i3.592 (19)H15···N4viii3.071 (17)
C12···H11i2.630 (18)H15···C3xiii3.508 (19)
C12···H192.543 (18)H15···C24ix3.043 (19)
C12···H19i3.099 (18)H15···H2xiii2.73 (3)
C12···H203.245 (19)H15···H13viii2.94 (3)
C12···H213.274 (18)H16···N2ix3.431 (16)
C12···H223.00 (2)H16···C25ix3.544 (18)
C12···H232.804 (15)H16···H2xiii3.00 (3)
C12···H23i3.324 (19)H16···H17xiii2.93 (3)
C13···H11i3.309 (18)H17···N2ii2.87 (3)
C13···H123.339 (14)H17···N4viii3.15 (3)
C13···H133.388 (16)H17···C25ii3.27 (3)
C13···H142.715 (16)H17···H2xiii2.65 (3)
C13···H163.165 (19)H17···H16xiii2.93 (3)
C13···H19i2.809 (18)H17···H19xiv3.54 (3)
C13···H232.842 (14)H18···N1x3.39 (3)
C13···H243.394 (15)H18···N2ii3.55 (3)
C14···H113.302 (14)H18···N4viii3.29 (3)
C14···H153.390 (19)H18···C7x3.476 (17)
C14···H162.82 (2)H18···H6x2.64 (3)
C14···H212.643 (15)H18···H7x3.40 (3)
C14···H222.905 (17)H18···H8x3.42 (3)
C15···H13.098 (18)H18···H14viii3.58 (3)
C15···H82.754 (18)H19···N2vi3.477 (18)
C15···H93.32 (3)H19···N4iii2.955 (19)
C15···H103.044 (19)H19···C29iii3.228 (19)
C15···H132.620 (19)H19···H17xv3.54 (3)
C15···H143.215 (17)H20···N2vi2.838 (19)
C16···H122.663 (17)H20···N4iii2.99 (2)
C16···H173.45 (3)H20···C8xi3.532 (18)
C16···H182.81 (2)H20···C29iii3.22 (3)
C16···H212.634 (14)H20···H7xi2.55 (3)
C16···H223.205 (15)H21···N2ix2.777 (17)
C17···H23.10 (3)H21···C25ix3.142 (17)
C17···H123.597 (17)H21···H5ix3.36 (4)
C17···H212.756 (15)H22···N3iii2.663 (19)
C18···H12.659 (18)H22···C7ix3.26 (2)
C18···H22.74 (2)H22···C273.549 (18)
C18···H123.556 (18)H22···C28iii2.927 (19)
C18···H132.78 (2)H22···H4ix3.25 (3)
C18···H143.449 (18)H22···H5ix2.39 (4)
C19···H92.574 (18)H22···H6ix3.35 (4)
C19···H103.277 (16)H23···N3iii3.336 (19)
C19···H112.610 (16)H24···N2ix2.740 (17)
C19···H11i3.005 (17)H24···N3xvi3.334 (16)
C19···H21i2.776 (17)H24···C25ix3.508 (17)
C19···H22i3.44 (2)H24···H4ix2.95 (4)
C20···H112.695 (17)
C2—C1—C6122.08 (13)N4—C29—C26162.91 (18)
C1—C2—C3118.44 (14)N4—C29—C27159.5 (2)
C1—C2—C18120.43 (13)C26—C29—C2737.62 (17)
C3—C2—C18121.03 (13)C2—C1—H1118.1 (11)
C2—C3—C4120.06 (13)C6—C1—H1119.8 (11)
C3—C4—C5120.49 (14)C2—C3—H2121.3 (13)
C4—C5—C6120.66 (15)C4—C3—H2118.6 (12)
C1—C6—C5118.04 (13)C3—C4—H3119.8 (12)
C1—C6—C7119.43 (14)C5—C4—H3119.7 (12)
C5—C6—C7122.39 (15)C4—C5—H4119.3 (12)
C6—C7—C8114.34 (15)C6—C5—H4120.1 (12)
C7—C8—C9116.32 (13)C6—C7—H5111.3 (15)
C8—C9—C10119.05 (14)C6—C7—H6111.8 (15)
C9—C10—C11120.79 (13)C8—C7—H5105.0 (19)
C9—C10—C15121.46 (11)C8—C7—H6109.9 (16)
C11—C10—C15117.74 (12)H5—C7—H6104 (3)
C10—C11—C12118.50 (13)C7—C8—H7109.4 (14)
C10—C11—C19123.07 (12)C7—C8—H8110.1 (12)
C12—C11—C19118.29 (10)C9—C8—H7106.1 (11)
C11—C12—C13123.50 (11)C9—C8—H8110.0 (10)
C12—C13—C14117.90 (12)H7—C8—H8104.2 (16)
C12—C13—C20120.57 (10)C8—C9—H9106.3 (12)
C14—C13—C20121.52 (12)C8—C9—H10109.4 (9)
C13—C14—C15118.34 (13)C10—C9—H9106.8 (11)
C13—C14—C16122.34 (12)C10—C9—H10108.3 (11)
C15—C14—C16119.33 (10)H9—C9—H10106.2 (17)
C10—C15—C14123.34 (11)C11—C12—H11117.0 (10)
C14—C16—C17116.14 (13)C13—C12—H11119.5 (10)
C16—C17—C18116.71 (12)C10—C15—H12118.4 (10)
C2—C18—C17113.70 (12)C14—C15—H12118.0 (10)
C11—C19—C21i112.79 (12)C14—C16—H13110.5 (10)
C13—C20—C21116.02 (12)C14—C16—H14107.8 (9)
C19i—C21—C20113.53 (11)C17—C16—H13108.5 (11)
C22ii—C22—C24113.7 (7)C17—C16—H14110.1 (10)
C22ii—C22—C25ii113.6 (6)H13—C16—H14103.0 (14)
C24—C22—C25ii132.7 (6)C16—C17—H15105.0 (12)
C23ii—C23—C24118.44 (17)C16—C17—H16112.2 (11)
C23ii—C23—C25119.30 (15)C18—C17—H15110.0 (11)
C24—C23—C25122.26 (15)C18—C17—H16108.7 (12)
N1—C24—C22148.2 (4)H15—C17—H16103.3 (15)
N1—C24—C23174.27 (19)C2—C18—H17109.3 (14)
C22—C24—C2337.5 (4)C2—C18—H18109.4 (13)
N2—C25—C22ii148.1 (3)C17—C18—H17107.9 (12)
N2—C25—C23174.49 (16)C17—C18—H18109.1 (13)
C22ii—C25—C2337.4 (3)H17—C18—H18107.2 (16)
C26iii—C26—C27iii44.2 (3)C11—C19—H19107.6 (10)
C26iii—C26—C28116.0 (3)C11—C19—H20110.4 (11)
C26iii—C26—C29116.9 (3)C21i—C19—H19110.1 (11)
C27iii—C26—C2871.8 (3)C21i—C19—H20109.6 (12)
C27iii—C26—C29161.1 (3)H19—C19—H20106.1 (14)
C28—C26—C29127.10 (18)C13—C20—H21107.6 (9)
C26iii—C27—C27iii44.5 (3)C13—C20—H22106.4 (10)
C26iii—C27—C28iii69.9 (3)C21—C20—H21108.8 (9)
C26iii—C27—C29161.3 (4)C21—C20—H22110.0 (9)
C27iii—C27—C28iii114.4 (3)H21—C20—H22107.8 (15)
C27iii—C27—C29116.8 (3)C19i—C21—H23109.4 (12)
C28iii—C27—C29128.8 (3)C19i—C21—H24109.3 (12)
N3—C28—C26163.7 (2)C20—C21—H23111.4 (9)
N3—C28—C27iii157.9 (3)C20—C21—H24106.3 (9)
C26—C28—C27iii38.33 (18)H23—C21—H24106.6 (13)
C2—C1—C6—C55.5 (3)C22ii—C22—C24—N1179.6 (5)
C2—C1—C6—C7−170.23 (13)C22ii—C22—C24—C23−0.7 (4)
C6—C1—C2—C3−5.2 (3)C24—C22—C22ii—C251.8 (9)
C6—C1—C2—C18171.25 (13)C22ii—C22—C25ii—N2ii−178.7 (5)
C1—C2—C3—C41.7 (2)C22ii—C22—C25ii—C23ii0.7 (4)
C1—C2—C18—C17−111.99 (14)C25ii—C22—C22ii—C24ii−1.8 (9)
C3—C2—C18—C1764.33 (19)C24—C22—C25ii—N2ii−1.0 (13)
C18—C2—C3—C4−174.72 (13)C24—C22—C25ii—C23ii178.4 (11)
C2—C3—C4—C51.3 (3)C25ii—C22—C24—N11.9 (13)
C3—C4—C5—C6−0.9 (3)C25ii—C22—C24—C23−178.4 (11)
C4—C5—C6—C1−2.4 (3)C23ii—C23—C24—C220.71 (12)
C4—C5—C6—C7173.19 (14)C24—C23—C23ii—C25ii0.0 (3)
C1—C6—C7—C861.87 (19)C23ii—C23—C25—C22ii0.72 (12)
C5—C6—C7—C8−113.71 (18)C25—C23—C23ii—C24ii−0.0 (3)
C6—C7—C8—C960.3 (2)C24—C23—C25—C22ii−179.3 (3)
C7—C8—C9—C10−77.14 (19)C25—C23—C24—C22−179.3 (3)
C8—C9—C10—C11151.51 (14)C26iii—C26—C27iii—C270 (12936568)
C8—C9—C10—C15−29.5 (2)C26iii—C26—C27iii—C28−179.6 (4)
C9—C10—C11—C12179.26 (13)C27iii—C26—C26iii—C28iii−179.6 (5)
C9—C10—C11—C19−5.1 (3)C27iii—C26—C26iii—C29iii−0.2 (4)
C9—C10—C15—C14173.81 (13)C26iii—C26—C28—C27iii0.30 (17)
C11—C10—C15—C14−7.2 (3)C28—C26—C26iii—C27179.6 (4)
C15—C10—C11—C120.2 (2)C28—C26—C26iii—C29iii−0.6 (4)
C15—C10—C11—C19175.82 (12)C26iii—C26—C29—C27−0.16 (17)
C10—C11—C12—C136.5 (3)C29—C26—C26iii—C270.2 (3)
C10—C11—C19—C21i−76.48 (16)C29—C26—C26iii—C28iii0.6 (4)
C12—C11—C19—C21i99.13 (14)C28—C26—C27iii—C27179.6 (3)
C19—C11—C12—C13−169.30 (12)C28—C26—C29—C27−179.5 (4)
C11—C12—C13—C14−6.3 (3)C29—C26—C28—C27iii179.6 (4)
C11—C12—C13—C20173.34 (13)C26iii—C27—C27iii—C28−179.6 (5)
C12—C13—C14—C15−0.6 (2)C26iii—C27—C27iii—C29iii0.2 (4)
C12—C13—C14—C16179.13 (12)C26iii—C27—C28iii—N3iii−178.8 (6)
C12—C13—C20—C21−24.0 (2)C27iii—C27—C28iii—N3iii−178.5 (5)
C14—C13—C20—C21155.60 (13)C27iii—C27—C28iii—C26iii0.3 (2)
C20—C13—C14—C15179.77 (12)C28iii—C27—C27iii—C26179.6 (5)
C20—C13—C14—C16−0.5 (3)C28iii—C27—C27iii—C29iii−0.2 (5)
C13—C14—C15—C107.4 (3)C27iii—C27—C29—N4−177.8 (5)
C13—C14—C16—C17−78.71 (17)C27iii—C27—C29—C260.2 (2)
C15—C14—C16—C17101.02 (14)C29—C27—C27iii—C26−0.2 (3)
C16—C14—C15—C10−172.37 (13)C29—C27—C27iii—C280.2 (5)
C14—C16—C17—C18−75.03 (13)C28iii—C27—C29—N42.4 (9)
C16—C17—C18—C269.70 (16)C28iii—C27—C29—C26−179.6 (6)
C11—C19—C21i—C20i−122.71 (10)C29—C27—C28iii—N3iii1.3 (9)
C13—C20—C21—C19i−62.02 (16)C29—C27—C28iii—C26iii−179.9 (6)
Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+1, −z+1; (iii) −x+1, −y, −z; (iv) x, y+1, z; (v) x−1, y, z; (vi) −x, −y+1, −z; (vii) x+1, y, z; (viii) −x+1, −y, −z+1; (ix) x, y−1, z; (x) −x+1, −y+1, −z+1; (xi) −x+1, −y+1, −z; (xii) x+1, y+1, z; (xiii) −x, −y, −z+1; (xiv) x, y, z+1; (xv) x, y, z−1; (xvi) x−1, y−1, z.

Experimental details

Crystal data
Chemical formulaC42H48·2C6N4
Mr809.03
Crystal system, space groupTriclinic, P1
Temperature (K)123
a, b, c (Å)9.563 (3), 10.101 (4), 11.679 (4)
α, β, γ (°)96.365 (14), 99.134 (13), 107.683 (13)
V (Å3)1045.9 (6)
Z1
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.35 × 0.16 × 0.09
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correction–
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections		17470, 4775, 4141
Rint0.050
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.178, 1.00
No. of reflections4775
No. of parameters394
H-atom treatmentOnly H-atom coordinates refined
Δρmax, Δρmin (e Å−3)0.80, −0.50

Computer programs: RAPID-AUTO (Rigaku, 1998), SHELXD (Schneider & Sheldrick, 2002), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).

Selected geometric parameters (Å, º) top
N1—C241.1223 (19)C13—C201.5178 (18)
N2—C251.126 (3)C14—C151.3997 (18)
N3—C281.124 (2)C14—C161.520 (2)
N4—C291.113 (3)C16—C171.547 (3)
C1—C21.3873 (19)C17—C181.540 (3)
C1—C61.400 (3)C19—C21i1.557 (3)
C2—C31.4000 (19)C20—C211.5323 (17)
C2—C181.509 (3)C22—C22ii1.333 (11)
C3—C41.389 (3)C22—C241.504 (7)
C4—C51.386 (3)C22—C25ii1.504 (8)
C5—C61.391 (3)C23—C23ii1.354 (3)
C6—C71.510 (3)C23—C241.454 (3)
C7—C81.529 (3)C23—C251.447 (3)
C8—C91.517 (2)C26—C26iii1.362 (4)
C9—C101.5221 (19)C26—C27iii0.972 (5)
C10—C111.4037 (16)C26—C281.472 (4)
C10—C151.403 (2)C26—C291.472 (4)
C11—C121.3975 (19)C27—C27iii1.356 (6)
C11—C191.519 (2)C27—C28iii1.488 (4)
C12—C131.398 (2)C27—C291.475 (4)
C13—C141.4052 (16)
C2—C1—C6122.08 (13)C19i—C21—C20113.53 (11)
C1—C2—C3118.44 (14)C22ii—C22—C24113.7 (7)
C1—C2—C18120.43 (13)C22ii—C22—C25ii113.6 (6)
C3—C2—C18121.03 (13)C24—C22—C25ii132.7 (6)
C2—C3—C4120.06 (13)C23ii—C23—C24118.44 (17)
C3—C4—C5120.49 (14)C23ii—C23—C25119.30 (15)
C4—C5—C6120.66 (15)C24—C23—C25122.26 (15)
C1—C6—C5118.04 (13)N1—C24—C22148.2 (4)
C1—C6—C7119.43 (14)N1—C24—C23174.27 (19)
C5—C6—C7122.39 (15)C22—C24—C2337.5 (4)
C6—C7—C8114.34 (15)N2—C25—C22ii148.1 (3)
C7—C8—C9116.32 (13)N2—C25—C23174.49 (16)
C8—C9—C10119.05 (14)C22ii—C25—C2337.4 (3)
C9—C10—C11120.79 (13)C26iii—C26—C27iii44.2 (3)
C9—C10—C15121.46 (11)C26iii—C26—C28116.0 (3)
C11—C10—C15117.74 (12)C26iii—C26—C29116.9 (3)
C10—C11—C12118.50 (13)C27iii—C26—C2871.8 (3)
C10—C11—C19123.07 (12)C27iii—C26—C29161.1 (3)
C12—C11—C19118.29 (10)C28—C26—C29127.10 (18)
C11—C12—C13123.50 (11)C26iii—C27—C27iii44.5 (3)
C12—C13—C14117.90 (12)C26iii—C27—C28iii69.9 (3)
C12—C13—C20120.57 (10)C26iii—C27—C29161.3 (4)
C14—C13—C20121.52 (12)C27iii—C27—C28iii114.4 (3)
C13—C14—C15118.34 (13)C27iii—C27—C29116.8 (3)
C13—C14—C16122.34 (12)C28iii—C27—C29128.8 (3)
C15—C14—C16119.33 (10)N3—C28—C26163.7 (2)
C10—C15—C14123.34 (11)N3—C28—C27iii157.9 (3)
C14—C16—C17116.14 (13)C26—C28—C27iii38.33 (18)
C16—C17—C18116.71 (12)N4—C29—C26162.91 (18)
C2—C18—C17113.70 (12)N4—C29—C27159.5 (2)
C11—C19—C21i112.79 (12)C26—C29—C2737.62 (17)
C13—C20—C21116.02 (12)
Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+1, −z+1; (iii) −x+1, −y, −z.
 

Acknowledgements

This work was partially supported by a Grant-in-Aid for Science Research (C 25410050) from the Japan Society for the Promotion of Science (JSPS), Japan, and was performed under the Cooperative Research Program of the Network Joint Research Center for Materials and Devices (IMCE, Kyushu University). MW thanks the World Premier Inter­national Research Center Initiative (WPI), Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT), Japan.

References

First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationRigaku (2010). CrystalStructure. Rigaku, Corporation, Tokyo, Japan.  Google Scholar
 First citationSchneider, T. R. & Sheldrick, G. M. (2002). Acta Cryst. D58, 1772–1779.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationShibahara, M., Watanabe, M., Chan, Y., Goto, K. & Shinmyozu, T. (2011a). Tetrahedron Lett. 52, 3371–3375.  Web of Science CSD CrossRef CAS Google Scholar
 First citationShibahara, M., Watanabe, M., Chan, Y. & Shinmyozu, T. (2011b). Tetrahedron Lett. 52, 5012–5015.  Web of Science CSD CrossRef CAS Google Scholar
 First citationShibahara, M., Watanabe, M., Iwanaga, T., Ideta, K. & Shinmyozu, T. (2007). J. Org. Chem. 72, 2865–2877.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationShibahara, M., Watanabe, M., Iwanaga, T., Matsumoto, T., Ideta, K. & Shinmyozu, T. (2008). J. Org. Chem. 73, 4433–4442.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationVögtle, F. (1993). In Cyclophane Chemistry. England: John Wiley & Sons Ltd.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 5| May 2014| Pages o625-o626
doi:10.1107/S1600536814009362
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS