organic compounds
Four-layered [3.3]metacyclophane with ethenetetracarbonitrile
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
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). 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
Crystal data
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Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO; data reduction: RAPID-AUTO; 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.
Supporting information
CCDC reference: 999480
10.1107/S1600536814009362/gw2145sup1.cif
contains datablocks General, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814009362/gw2145Isup2.hkl
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.
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.
Data collection: RAPID-AUTO (Rigaku, 1998); cell
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).C42H48·2C6N4 | Z = 1 |
Mr = 809.03 | F(000) = 428.00 |
Triclinic, P1 | Dx = 1.284 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71075 Å |
a = 9.563 (3) Å | Cell parameters from 13845 reflections |
b = 10.101 (4) Å | θ = 3.0–27.5° |
c = 11.679 (4) Å | µ = 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 |
Rigaku R-AXIS RAPID diffractometer | Rint = 0.050 |
ω/2θ scans | θmax = 27.5° |
17470 measured reflections | h = −12→11 |
4775 independent reflections | k = −13→13 |
4141 reflections with F2 > 2σ(F2) | l = −15→15 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.178 | Only 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 parameters | Δρmax = 0.80 e Å−3 |
0 restraints | Δρmin = −0.50 e Å−3 |
Primary atom site location: structure-invariant direct methods |
C42H48·2C6N4 | γ = 107.683 (13)° |
Mr = 809.03 | V = 1045.9 (6) Å3 |
Triclinic, P1 | Z = 1 |
a = 9.563 (3) Å | Mo Kα radiation |
b = 10.101 (4) Å | µ = 0.08 mm−1 |
c = 11.679 (4) Å | T = 123 K |
α = 96.365 (14)° | 0.35 × 0.16 × 0.09 mm |
β = 99.134 (13)° |
Rigaku R-AXIS RAPID diffractometer | 4141 reflections with F2 > 2σ(F2) |
17470 measured reflections | Rint = 0.050 |
4775 independent reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.178 | Only H-atom coordinates refined |
S = 1.00 | Δρmax = 0.80 e Å−3 |
4775 reflections | Δρmin = −0.50 e Å−3 |
394 parameters |
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). |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.30526 (16) | 0.71021 (14) | 0.53324 (14) | 0.0447 (4) | |
N2 | −0.13890 (17) | 0.62272 (16) | 0.31010 (12) | 0.0437 (4) | |
N3 | 0.70465 (15) | 0.29951 (14) | 0.04664 (13) | 0.0426 (4) | |
N4 | 0.63339 (18) | −0.04481 (19) | 0.23634 (12) | 0.0507 (4) | |
C1 | 0.27496 (16) | 0.35932 (14) | 0.38821 (12) | 0.0292 (3) | |
C2 | 0.17966 (15) | 0.23727 (14) | 0.41376 (11) | 0.0271 (3) | |
C3 | 0.02899 (16) | 0.18988 (15) | 0.35613 (12) | 0.0308 (3) | |
C4 | −0.02123 (17) | 0.26252 (16) | 0.27325 (13) | 0.0344 (4) | |
C5 | 0.07747 (18) | 0.38055 (16) | 0.24516 (12) | 0.0344 (4) | |
C6 | 0.22797 (17) | 0.42945 (14) | 0.30050 (13) | 0.0314 (4) | |
C7 | 0.3425 (3) | 0.54751 (16) | 0.26353 (17) | 0.0421 (4) | |
C8 | 0.46096 (18) | 0.50271 (16) | 0.21084 (14) | 0.0379 (4) | |
C9 | 0.40369 (16) | 0.39146 (14) | 0.10058 (13) | 0.0306 (3) | |
C10 | 0.33220 (14) | 0.23804 (13) | 0.11189 (12) | 0.0247 (3) | |
C11 | 0.22263 (14) | 0.14374 (13) | 0.01981 (11) | 0.0232 (3) | |
C12 | 0.16183 (14) | 0.00361 (13) | 0.03416 (11) | 0.0237 (3) | |
C13 | 0.19319 (14) | −0.04508 (13) | 0.13956 (11) | 0.0232 (3) | |
C14 | 0.30253 (14) | 0.04905 (13) | 0.23209 (11) | 0.0235 (3) | |
C15 | 0.37473 (14) | 0.18541 (13) | 0.21330 (12) | 0.0251 (3) | |
C16 | 0.34394 (15) | 0.00796 (14) | 0.35098 (12) | 0.0271 (3) | |
C17 | 0.23470 (17) | 0.00835 (14) | 0.43550 (12) | 0.0309 (3) | |
C18 | 0.23976 (18) | 0.15347 (15) | 0.49632 (12) | 0.0332 (4) | |
C19 | 0.15916 (14) | 0.18891 (14) | −0.09117 (11) | 0.0248 (3) | |
C20 | 0.11033 (14) | −0.19487 (13) | 0.15283 (12) | 0.0253 (3) | |
C21 | −0.04379 (14) | −0.26541 (13) | 0.07162 (11) | 0.0240 (3) | |
C22 | 0.0677 (9) | 0.5125 (7) | 0.5331 (7) | 0.0274 (14) | 0.2000 |
C23 | 0.0276 (2) | 0.55598 (17) | 0.47359 (15) | 0.0251 (4) | 0.8000 |
C24 | 0.18542 (17) | 0.63929 (15) | 0.51109 (13) | 0.0343 (4) | |
C25 | −0.07150 (17) | 0.58885 (15) | 0.38230 (12) | 0.0332 (4) | |
C26 | 0.5541 (3) | 0.0410 (3) | 0.0464 (3) | 0.0283 (5) | 0.5600 |
C27 | 0.4895 (4) | −0.0541 (4) | 0.0308 (3) | 0.0263 (6) | 0.4400 |
C28 | 0.62892 (17) | 0.18694 (17) | 0.03210 (17) | 0.0426 (4) | |
C29 | 0.58456 (17) | −0.02573 (17) | 0.14916 (13) | 0.0354 (4) | |
H1 | 0.383 (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)* | |
H4 | 0.041 (3) | 0.428 (3) | 0.1855 (19) | 0.050 (6)* | |
H5 | 0.297 (3) | 0.587 (3) | 0.205 (3) | 0.081 (8)* | |
H6 | 0.390 (3) | 0.626 (3) | 0.327 (2) | 0.058 (6)* | |
H7 | 0.534 (3) | 0.588 (3) | 0.1889 (17) | 0.051 (6)* | |
H8 | 0.530 (3) | 0.469 (2) | 0.2774 (17) | 0.042 (5)* | |
H9 | 0.322 (3) | 0.419 (3) | 0.0470 (18) | 0.051 (6)* | |
H10 | 0.488 (2) | 0.3976 (19) | 0.0554 (16) | 0.043 (5)* | |
H11 | 0.0882 (17) | −0.0620 (16) | −0.0336 (14) | 0.021 (4)* | |
H12 | 0.4578 (18) | 0.2534 (17) | 0.2809 (14) | 0.027 (4)* | |
H13 | 0.452 (2) | 0.0727 (18) | 0.3944 (15) | 0.033 (5)* | |
H14 | 0.3556 (17) | −0.0871 (17) | 0.3366 (13) | 0.024 (4)* | |
H15 | 0.260 (2) | −0.0488 (19) | 0.4963 (16) | 0.038 (5)* | |
H16 | 0.125 (2) | −0.0487 (19) | 0.3960 (16) | 0.037 (5)* | |
H17 | 0.179 (3) | 0.138 (2) | 0.5597 (18) | 0.048 (5)* | |
H18 | 0.352 (3) | 0.212 (3) | 0.5384 (18) | 0.050 (6)* | |
H19 | 0.1086 (18) | 0.0987 (18) | −0.1549 (14) | 0.029 (4)* | |
H20 | 0.242 (2) | 0.2516 (18) | −0.1231 (15) | 0.034 (5)* | |
H21 | 0.0979 (19) | −0.1933 (17) | 0.2372 (14) | 0.029 (4)* | |
H22 | 0.1777 (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)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0341 (8) | 0.0348 (7) | 0.0587 (9) | 0.0038 (6) | 0.0098 (6) | 0.0017 (6) |
N2 | 0.0523 (9) | 0.0596 (9) | 0.0346 (7) | 0.0334 (7) | 0.0143 (6) | 0.0209 (7) |
N3 | 0.0335 (7) | 0.0360 (7) | 0.0599 (9) | 0.0112 (6) | 0.0152 (6) | 0.0066 (6) |
N4 | 0.0539 (9) | 0.0834 (12) | 0.0354 (8) | 0.0470 (9) | 0.0129 (7) | 0.0190 (7) |
C1 | 0.0316 (8) | 0.0267 (7) | 0.0322 (7) | 0.0119 (6) | 0.0093 (6) | 0.0056 (6) |
C2 | 0.0324 (7) | 0.0262 (7) | 0.0252 (7) | 0.0116 (6) | 0.0086 (5) | 0.0048 (5) |
C3 | 0.0321 (8) | 0.0283 (7) | 0.0326 (7) | 0.0101 (6) | 0.0100 (6) | 0.0023 (6) |
C4 | 0.0354 (8) | 0.0381 (8) | 0.0310 (7) | 0.0181 (6) | 0.0033 (6) | −0.0021 (6) |
C5 | 0.0500 (9) | 0.0357 (8) | 0.0272 (7) | 0.0266 (7) | 0.0097 (6) | 0.0064 (6) |
C6 | 0.0422 (8) | 0.0266 (7) | 0.0336 (7) | 0.0178 (6) | 0.0160 (6) | 0.0077 (6) |
C7 | 0.0601 (11) | 0.0261 (7) | 0.0492 (10) | 0.0170 (7) | 0.0262 (8) | 0.0138 (7) |
C8 | 0.0360 (8) | 0.0302 (7) | 0.0450 (9) | 0.0051 (6) | 0.0083 (7) | 0.0134 (7) |
C9 | 0.0333 (8) | 0.0256 (7) | 0.0385 (8) | 0.0108 (6) | 0.0145 (6) | 0.0144 (6) |
C10 | 0.0235 (7) | 0.0250 (6) | 0.0318 (7) | 0.0118 (5) | 0.0111 (5) | 0.0119 (5) |
C11 | 0.0222 (6) | 0.0262 (6) | 0.0288 (7) | 0.0136 (5) | 0.0102 (5) | 0.0121 (5) |
C12 | 0.0211 (6) | 0.0263 (7) | 0.0285 (7) | 0.0113 (5) | 0.0080 (5) | 0.0104 (5) |
C13 | 0.0214 (6) | 0.0251 (6) | 0.0294 (7) | 0.0124 (5) | 0.0087 (5) | 0.0111 (5) |
C14 | 0.0219 (6) | 0.0265 (6) | 0.0279 (7) | 0.0130 (5) | 0.0081 (5) | 0.0104 (5) |
C15 | 0.0235 (7) | 0.0260 (7) | 0.0296 (7) | 0.0110 (5) | 0.0079 (5) | 0.0088 (5) |
C16 | 0.0282 (7) | 0.0271 (7) | 0.0285 (7) | 0.0115 (5) | 0.0043 (5) | 0.0104 (5) |
C17 | 0.0395 (8) | 0.0282 (7) | 0.0295 (7) | 0.0137 (6) | 0.0098 (6) | 0.0119 (6) |
C18 | 0.0447 (9) | 0.0305 (7) | 0.0274 (7) | 0.0153 (6) | 0.0073 (6) | 0.0088 (6) |
C19 | 0.0249 (7) | 0.0279 (7) | 0.0275 (7) | 0.0125 (5) | 0.0087 (5) | 0.0126 (5) |
C20 | 0.0249 (7) | 0.0249 (6) | 0.0308 (7) | 0.0115 (5) | 0.0073 (5) | 0.0126 (5) |
C21 | 0.0266 (7) | 0.0223 (6) | 0.0268 (7) | 0.0113 (5) | 0.0065 (5) | 0.0086 (5) |
C22 | 0.040 (5) | 0.017 (3) | 0.031 (4) | 0.010 (4) | 0.019 (3) | 0.012 (3) |
C23 | 0.0266 (10) | 0.0231 (8) | 0.0266 (9) | 0.0084 (8) | 0.0064 (7) | 0.0061 (7) |
C24 | 0.0343 (8) | 0.0280 (7) | 0.0386 (8) | 0.0063 (6) | 0.0121 (6) | 0.0022 (6) |
C25 | 0.0437 (9) | 0.0334 (7) | 0.0293 (7) | 0.0195 (6) | 0.0101 (6) | 0.0101 (6) |
C26 | 0.0248 (12) | 0.0312 (16) | 0.0336 (16) | 0.0135 (12) | 0.0075 (11) | 0.0101 (11) |
C27 | 0.0206 (14) | 0.0318 (19) | 0.0283 (17) | 0.0114 (14) | 0.0046 (12) | 0.0046 (14) |
C28 | 0.0300 (8) | 0.0343 (8) | 0.0663 (11) | 0.0112 (7) | 0.0186 (7) | 0.0048 (8) |
C29 | 0.0316 (8) | 0.0508 (9) | 0.0325 (8) | 0.0241 (7) | 0.0081 (6) | 0.0110 (7) |
N1—C24 | 1.1223 (19) | C23—C25 | 1.447 (3) |
N2—C25 | 1.126 (3) | C26—C26iii | 1.362 (4) |
N3—C28 | 1.124 (2) | C26—C27iii | 0.972 (5) |
N4—C29 | 1.113 (3) | C26—C28 | 1.472 (4) |
C1—C2 | 1.3873 (19) | C26—C29 | 1.472 (4) |
C1—C6 | 1.400 (3) | C27—C27iii | 1.356 (6) |
C2—C3 | 1.4000 (19) | C27—C28iii | 1.488 (4) |
C2—C18 | 1.509 (3) | C27—C29 | 1.475 (4) |
C3—C4 | 1.389 (3) | C1—H1 | 1.007 (17) |
C4—C5 | 1.386 (3) | C3—H2 | 1.01 (2) |
C5—C6 | 1.391 (3) | C4—H3 | 1.015 (19) |
C6—C7 | 1.510 (3) | C5—H4 | 0.97 (3) |
C7—C8 | 1.529 (3) | C7—H5 | 0.95 (3) |
C8—C9 | 1.517 (2) | C7—H6 | 0.96 (2) |
C9—C10 | 1.5221 (19) | C8—H7 | 1.02 (2) |
C10—C11 | 1.4037 (16) | C8—H8 | 1.09 (2) |
C10—C15 | 1.403 (2) | C9—H9 | 1.05 (3) |
C11—C12 | 1.3975 (19) | C9—H10 | 1.02 (2) |
C11—C19 | 1.519 (2) | C12—H11 | 0.992 (13) |
C12—C13 | 1.398 (2) | C15—H12 | 1.037 (14) |
C13—C14 | 1.4052 (16) | C16—H13 | 1.047 (15) |
C13—C20 | 1.5178 (18) | C16—H14 | 0.999 (18) |
C14—C15 | 1.3997 (18) | C17—H15 | 1.01 (2) |
C14—C16 | 1.520 (2) | C17—H16 | 1.029 (17) |
C16—C17 | 1.547 (3) | C18—H17 | 1.01 (3) |
C17—C18 | 1.540 (3) | C18—H18 | 1.060 (19) |
C19—C21i | 1.557 (3) | C19—H19 | 1.042 (15) |
C20—C21 | 1.5323 (17) | C19—H20 | 1.006 (18) |
C22—C22ii | 1.333 (11) | C20—H21 | 1.010 (18) |
C22—C24 | 1.504 (7) | C20—H22 | 1.00 (2) |
C22—C25ii | 1.504 (8) | C21—H23 | 0.991 (18) |
C23—C23ii | 1.354 (3) | C21—H24 | 0.996 (18) |
C23—C24 | 1.454 (3) | ||
N1···C22ii | 3.499 (8) | C20···H14 | 2.762 (14) |
N1···C23ii | 3.470 (3) | C20···H16 | 3.013 (18) |
N1···C25 | 3.523 (3) | C20···H19i | 2.56 (2) |
N1···C25ii | 3.515 (3) | C20···H20i | 3.198 (19) |
N2···C22 | 3.503 (8) | C21···H4i | 3.27 (3) |
N2···C23ii | 3.478 (3) | C21···H9i | 2.697 (19) |
N2···C24 | 3.528 (3) | C21···H11 | 2.608 (16) |
N2···C24ii | 3.517 (3) | C21···H11i | 3.526 (18) |
N3···C26iii | 3.504 (3) | H1···H5 | 3.59 (4) |
N3···C27 | 3.506 (4) | H1···H6 | 2.74 (4) |
N3···C29 | 3.544 (3) | H1···H8 | 2.50 (3) |
N3···C29iii | 3.531 (2) | H1···H12 | 2.47 (3) |
N4···C26iii | 3.509 (4) | H1···H13 | 3.50 (3) |
N4···C27iii | 3.514 (4) | H1···H17 | 3.39 (3) |
N4···C28 | 3.527 (3) | H1···H18 | 2.31 (3) |
N4···C28iii | 3.535 (3) | H2···H3 | 2.38 (3) |
C1···C4 | 2.757 (2) | H2···H16 | 2.54 (4) |
C1···C8 | 3.134 (3) | H2···H17 | 2.72 (3) |
C1···C10 | 3.508 (3) | H2···H19i | 2.91 (3) |
C1···C14 | 3.550 (3) | H3···H4 | 2.36 (3) |
C1···C15 | 3.002 (3) | H3···H11i | 2.86 (3) |
C1···C17 | 3.563 (3) | H3···H19i | 3.40 (3) |
C2···C5 | 2.794 (3) | H3···H23i | 3.23 (3) |
C2···C14 | 3.279 (3) | H4···H5 | 2.44 (3) |
C2···C15 | 3.308 (3) | H4···H6 | 3.37 (3) |
C2···C16 | 3.251 (3) | H4···H9 | 3.37 (4) |
C3···C6 | 2.800 (2) | H4···H23i | 2.39 (3) |
C3···C17 | 3.175 (3) | H4···H24i | 3.30 (3) |
C5···C8 | 3.600 (3) | H5···H7 | 2.30 (4) |
C6···C9 | 3.140 (3) | H5···H8 | 2.89 (4) |
C6···C10 | 3.241 (3) | H5···H9 | 2.45 (4) |
C6···C15 | 3.329 (3) | H5···H10 | 3.53 (4) |
C7···C10 | 3.383 (3) | H6···H7 | 2.35 (4) |
C8···C15 | 3.062 (3) | H6···H8 | 2.44 (4) |
C9···C19 | 3.0140 (18) | H6···H9 | 3.53 (3) |
C9···C21i | 3.476 (2) | H7···H9 | 2.44 (3) |
C10···C13 | 2.843 (2) | H7···H10 | 2.22 (3) |
C10···C21i | 3.316 (2) | H7···H12 | 3.56 (3) |
C11···C12i | 3.444 (2) | H8···H9 | 2.97 (3) |
C11···C14 | 2.831 (2) | H8···H10 | 2.55 (3) |
C12···C12i | 3.048 (2) | H8···H12 | 2.09 (3) |
C12···C15 | 2.7237 (17) | H9···H20 | 2.32 (3) |
C12···C19i | 3.310 (2) | H9···H23i | 2.63 (3) |
C12···C21 | 2.9550 (19) | H9···H24i | 2.45 (3) |
C12···C21i | 3.448 (3) | H10···H12 | 3.16 (3) |
C13···C17 | 3.379 (3) | H10···H20 | 2.78 (3) |
C13···C19i | 3.1660 (19) | H11···H11i | 2.55 (3) |
C14···C18 | 3.354 (3) | H11···H19 | 2.26 (3) |
C15···C17 | 3.522 (3) | H11···H19i | 3.10 (3) |
C16···C20 | 3.0117 (18) | H11···H20 | 3.42 (3) |
C17···C20 | 3.506 (2) | H11···H21 | 3.56 (3) |
N1···C6 | 3.515 (3) | H11···H22 | 3.12 (3) |
N1···C7 | 3.509 (3) | H11···H23 | 2.18 (3) |
N1···C17iv | 3.547 (3) | H11···H23i | 3.58 (3) |
N2···C2ii | 3.504 (3) | H11···H24 | 3.55 (3) |
N2···C8v | 3.594 (3) | H12···H13 | 2.36 (3) |
N2···C18ii | 3.469 (3) | H12···H14 | 3.44 (3) |
N2···C19vi | 3.368 (3) | H12···H18 | 3.35 (3) |
N2···C20iv | 3.453 (3) | H13···H15 | 2.43 (3) |
N2···C21iv | 3.277 (3) | H13···H16 | 2.99 (3) |
N3···C4vii | 3.553 (3) | H13···H18 | 2.55 (3) |
N3···C9 | 3.408 (3) | H14···H15 | 2.25 (3) |
N3···C20iii | 3.402 (3) | H14···H16 | 2.53 (3) |
N4···C14 | 3.563 (3) | H14···H21 | 2.40 (2) |
N4···C16 | 3.414 (3) | H14···H22 | 2.67 (2) |
N4···C18viii | 3.576 (3) | H15···H17 | 2.33 (4) |
N4···C19iii | 3.347 (3) | H15···H18 | 2.48 (3) |
C1···C22 | 3.396 (9) | H15···H21 | 3.14 (3) |
C1···C24 | 3.428 (3) | H16···H17 | 2.40 (3) |
C2···N2ii | 3.504 (3) | H16···H18 | 2.97 (3) |
C2···C22 | 3.499 (9) | H16···H19i | 3.19 (3) |
C2···C23ii | 3.571 (3) | H16···H21 | 2.16 (3) |
C2···C25ii | 3.284 (3) | H19···H21i | 2.55 (3) |
C3···C22 | 3.544 (8) | H19···H22i | 3.54 (3) |
C3···C22ii | 3.573 (9) | H19···H23i | 2.80 (3) |
C3···C23ii | 3.300 (3) | H19···H24i | 2.80 (3) |
C3···C24ii | 3.486 (3) | H20···H21i | 3.16 (3) |
C3···C25ii | 3.469 (3) | H20···H23i | 2.76 (3) |
C4···N3v | 3.553 (3) | H20···H24i | 2.22 (3) |
C4···C22 | 3.534 (7) | H21···H23 | 2.91 (3) |
C4···C22ii | 3.204 (8) | H21···H24 | 2.346 (19) |
C4···C23 | 3.428 (3) | H22···H23 | 2.41 (3) |
C4···C23ii | 3.321 (3) | H22···H24 | 2.33 (3) |
C4···C24ii | 3.382 (3) | N1···H1x | 3.44 (2) |
C4···C25 | 3.598 (3) | N1···H3ii | 3.52 (3) |
C5···C22 | 3.504 (8) | N1···H6 | 2.79 (3) |
C5···C22ii | 3.351 (9) | N1···H8x | 3.49 (3) |
C5···C23 | 3.218 (3) | N1···H12x | 2.781 (16) |
C5···C25 | 3.289 (3) | N1···H13x | 2.607 (15) |
C6···N1 | 3.515 (3) | N1···H14iv | 3.239 (17) |
C6···C22 | 3.468 (9) | N1···H15iv | 2.67 (2) |
C6···C23 | 3.397 (3) | N1···H18x | 3.39 (3) |
C6···C24 | 3.224 (3) | N2···H4 | 3.34 (3) |
C7···N1 | 3.509 (3) | N2···H7v | 3.12 (2) |
C8···N2vii | 3.594 (3) | N2···H8v | 3.010 (19) |
C9···N3 | 3.408 (3) | N2···H16iv | 3.431 (16) |
C9···C28 | 3.526 (3) | N2···H17ii | 2.87 (3) |
C10···C26 | 3.434 (4) | N2···H18ii | 3.55 (3) |
C10···C27iii | 3.358 (5) | N2···H19vi | 3.477 (18) |
C10···C28 | 3.288 (3) | N2···H20vi | 2.838 (19) |
C11···C26iii | 3.356 (4) | N2···H21iv | 2.777 (17) |
C11···C27iii | 3.265 (5) | N2···H24iv | 2.740 (17) |
C11···C29iii | 3.269 (3) | N3···H3vii | 2.76 (2) |
C12···C26iii | 3.151 (4) | N3···H4vii | 3.16 (2) |
C12···C27 | 3.362 (5) | N3···H5xi | 3.27 (3) |
C12···C27iii | 3.436 (4) | N3···H9xi | 3.22 (3) |
C12···C28iii | 3.288 (3) | N3···H10 | 2.56 (3) |
C12···C29iii | 3.456 (3) | N3···H11iii | 3.550 (19) |
C13···C26iii | 3.491 (4) | N3···H22iii | 2.663 (19) |
C13···C27 | 3.305 (4) | N3···H23iii | 3.336 (19) |
C13···C28iii | 3.300 (3) | N3···H24xii | 3.334 (16) |
C14···N4 | 3.563 (3) | N4···H2vii | 3.055 (19) |
C14···C26 | 3.497 (4) | N4···H3vii | 2.996 (18) |
C14···C27 | 3.426 (5) | N4···H7ix | 3.49 (2) |
C14···C29 | 3.269 (3) | N4···H13 | 3.10 (2) |
C15···C26 | 3.289 (4) | N4···H14 | 3.003 (17) |
C15···C27 | 3.580 (5) | N4···H15viii | 3.071 (17) |
C15···C27iii | 3.599 (4) | N4···H17viii | 3.15 (3) |
C15···C28 | 3.465 (3) | N4···H18viii | 3.29 (3) |
C15···C29 | 3.444 (3) | N4···H19iii | 2.955 (19) |
C16···N4 | 3.414 (3) | N4···H20iii | 2.99 (2) |
C17···N1ix | 3.547 (3) | C3···H15xiii | 3.508 (19) |
C18···N2ii | 3.469 (3) | C7···H18x | 3.476 (17) |
C18···N4viii | 3.576 (3) | C7···H22iv | 3.26 (2) |
C19···N2vi | 3.368 (3) | C8···H10xi | 3.435 (19) |
C19···N4iii | 3.347 (3) | C8···H20xi | 3.532 (18) |
C19···C29iii | 3.452 (3) | C9···H7xi | 3.54 (2) |
C20···N2ix | 3.453 (3) | C9···H9xi | 3.55 (3) |
C20···N3iii | 3.402 (3) | C9···H10xi | 3.008 (19) |
C20···C28iii | 3.538 (3) | C17···H2xiii | 3.20 (3) |
C21···N2ix | 3.277 (3) | C18···H2xiii | 3.37 (2) |
C22···C1 | 3.396 (9) | C19···H7xi | 3.55 (2) |
C22···C2 | 3.499 (9) | C20···H5ix | 3.28 (4) |
C22···C3 | 3.544 (8) | C22···H3ii | 3.42 (2) |
C22···C3ii | 3.573 (9) | C23···H4 | 3.50 (3) |
C22···C4 | 3.534 (7) | C24···H2ii | 3.53 (3) |
C22···C4ii | 3.204 (8) | C24···H3ii | 3.33 (2) |
C22···C5 | 3.504 (8) | C24···H6 | 3.15 (3) |
C22···C5ii | 3.351 (9) | C24···H15iv | 3.043 (19) |
C22···C6 | 3.468 (9) | C25···H4 | 3.18 (3) |
C23···C2ii | 3.571 (3) | C25···H8v | 3.586 (19) |
C23···C3ii | 3.300 (3) | C25···H16iv | 3.544 (18) |
C23···C4 | 3.428 (3) | C25···H17ii | 3.27 (3) |
C23···C4ii | 3.321 (3) | C25···H21iv | 3.142 (17) |
C23···C5 | 3.218 (3) | C25···H24iv | 3.508 (17) |
C23···C6 | 3.397 (3) | C26···H3vii | 3.304 (17) |
C24···C1 | 3.428 (3) | C26···H11iii | 3.391 (18) |
C24···C3ii | 3.486 (3) | C27···H10iii | 3.58 (2) |
C24···C4ii | 3.382 (3) | C27···H22 | 3.549 (18) |
C24···C6 | 3.224 (3) | C28···H3vii | 2.900 (19) |
C25···C2ii | 3.284 (3) | C28···H10 | 2.85 (3) |
C25···C3ii | 3.469 (3) | C28···H11iii | 3.313 (19) |
C25···C4 | 3.598 (3) | C28···H22iii | 2.927 (19) |
C25···C5 | 3.289 (3) | C29···H3vii | 3.049 (17) |
C26···C10 | 3.434 (4) | C29···H11iii | 3.510 (17) |
C26···C11iii | 3.356 (4) | C29···H13 | 3.479 (19) |
C26···C12iii | 3.151 (4) | C29···H14 | 3.312 (17) |
C26···C13iii | 3.491 (4) | C29···H19iii | 3.228 (19) |
C26···C14 | 3.497 (4) | C29···H20iii | 3.22 (3) |
C26···C15 | 3.289 (4) | H1···N1x | 3.44 (2) |
C27···C10iii | 3.358 (5) | H1···H1x | 2.71 (2) |
C27···C11iii | 3.265 (5) | H1···H6x | 3.34 (3) |
C27···C12 | 3.362 (5) | H1···H8x | 3.39 (3) |
C27···C12iii | 3.436 (4) | H2···N4v | 3.055 (19) |
C27···C13 | 3.305 (4) | H2···C17xiii | 3.20 (3) |
C27···C14 | 3.426 (5) | H2···C18xiii | 3.37 (2) |
C27···C15 | 3.580 (5) | H2···C24ii | 3.53 (3) |
C27···C15iii | 3.599 (4) | H2···H15xiii | 2.73 (3) |
C28···C9 | 3.526 (3) | H2···H16xiii | 3.00 (3) |
C28···C10 | 3.288 (3) | H2···H17xiii | 2.65 (3) |
C28···C12iii | 3.288 (3) | H3···N1ii | 3.52 (3) |
C28···C13iii | 3.300 (3) | H3···N3v | 2.76 (2) |
C28···C15 | 3.465 (3) | H3···N4v | 2.996 (18) |
C28···C20iii | 3.538 (3) | H3···C22ii | 3.42 (2) |
C29···C11iii | 3.269 (3) | H3···C24ii | 3.33 (2) |
C29···C12iii | 3.456 (3) | H3···C26v | 3.304 (17) |
C29···C14 | 3.269 (3) | H3···C28v | 2.900 (19) |
C29···C15 | 3.444 (3) | H3···C29v | 3.049 (17) |
C29···C19iii | 3.452 (3) | H4···N2 | 3.34 (3) |
C1···H2 | 3.321 (19) | H4···N3v | 3.16 (2) |
C1···H4 | 3.27 (3) | H4···C23 | 3.50 (3) |
C1···H5 | 3.30 (3) | H4···C25 | 3.18 (3) |
C1···H6 | 2.80 (3) | H4···H22iv | 3.25 (3) |
C1···H8 | 2.92 (2) | H4···H24iv | 2.95 (4) |
C1···H12 | 2.70 (2) | H5···N3xi | 3.27 (3) |
C1···H17 | 3.19 (3) | H5···C20iv | 3.28 (4) |
C1···H18 | 2.58 (3) | H5···H14iv | 3.32 (4) |
C2···H3 | 3.33 (2) | H5···H21iv | 3.36 (4) |
C2···H12 | 3.257 (19) | H5···H22iv | 2.39 (4) |
C2···H13 | 3.51 (2) | H6···N1 | 2.79 (3) |
C2···H15 | 3.41 (2) | H6···C24 | 3.15 (3) |
C2···H16 | 2.75 (2) | H6···H1x | 3.34 (3) |
C3···H1 | 3.299 (16) | H6···H14iv | 3.01 (4) |
C3···H4 | 3.28 (3) | H6···H18x | 2.64 (3) |
C3···H16 | 2.89 (3) | H6···H22iv | 3.35 (4) |
C3···H17 | 2.77 (2) | H7···N2vii | 3.12 (2) |
C3···H18 | 3.39 (2) | H7···N4iv | 3.49 (2) |
C3···H19i | 3.304 (15) | H7···C9xi | 3.54 (2) |
C4···H11i | 3.119 (15) | H7···C19xi | 3.55 (2) |
C4···H19i | 3.547 (17) | H7···H9xi | 3.27 (4) |
C4···H23i | 3.189 (18) | H7···H10xi | 2.85 (3) |
C5···H1 | 3.308 (18) | H7···H18x | 3.40 (3) |
C5···H2 | 3.31 (2) | H7···H20xi | 2.55 (3) |
C5···H5 | 2.62 (3) | H8···N1x | 3.49 (3) |
C5···H6 | 3.17 (2) | H8···N2vii | 3.010 (19) |
C5···H9 | 3.52 (3) | H8···C25vii | 3.586 (19) |
C5···H11i | 3.587 (14) | H8···H1x | 3.39 (3) |
C5···H23i | 2.731 (17) | H8···H18x | 3.42 (3) |
C6···H3 | 3.327 (18) | H9···N3xi | 3.22 (3) |
C6···H7 | 3.41 (2) | H9···C9xi | 3.55 (3) |
C6···H8 | 2.86 (2) | H9···H7xi | 3.27 (4) |
C6···H9 | 3.23 (3) | H9···H10xi | 2.70 (3) |
C6···H12 | 3.24 (2) | H10···N3 | 2.56 (3) |
C6···H23i | 3.504 (15) | H10···C8xi | 3.435 (19) |
C7···H1 | 2.681 (19) | H10···C9xi | 3.008 (19) |
C7···H4 | 2.72 (2) | H10···C27iii | 3.58 (2) |
C7···H9 | 2.66 (2) | H10···C28 | 2.85 (3) |
C7···H10 | 3.42 (2) | H10···H7xi | 2.85 (3) |
C7···H12 | 3.484 (19) | H10···H9xi | 2.70 (3) |
C8···H1 | 3.023 (19) | H10···H10xi | 2.53 (3) |
C8···H12 | 2.726 (18) | H11···N3iii | 3.550 (19) |
C9···H5 | 2.74 (3) | H11···C26iii | 3.391 (18) |
C9···H6 | 3.39 (3) | H11···C28iii | 3.313 (19) |
C9···H12 | 2.719 (18) | H11···C29iii | 3.510 (17) |
C9···H20 | 2.789 (15) | H12···N1x | 2.781 (16) |
C9···H23i | 3.299 (16) | H13···N1x | 2.607 (15) |
C9···H24i | 3.410 (17) | H13···N4 | 3.10 (2) |
C10···H7 | 3.411 (19) | H13···C29 | 3.479 (19) |
C10···H8 | 2.817 (16) | H13···H13viii | 3.16 (3) |
C10···H11 | 3.289 (13) | H13···H14viii | 3.34 (3) |
C10···H19 | 3.368 (15) | H13···H15viii | 2.94 (3) |
C10···H20 | 2.773 (18) | H14···N1ix | 3.239 (17) |
C10···H23i | 3.033 (18) | H14···N4 | 3.003 (17) |
C11···H9 | 2.62 (2) | H14···C29 | 3.312 (17) |
C11···H10 | 2.944 (17) | H14···H5ix | 3.32 (4) |
C11···H11i | 2.870 (16) | H14···H6ix | 3.01 (4) |
C11···H12 | 3.338 (15) | H14···H13viii | 3.34 (3) |
C11···H23i | 2.52 (2) | H14···H18viii | 3.58 (3) |
C11···H24i | 3.20 (2) | H15···N1ix | 2.67 (2) |
C12···H3i | 3.592 (19) | H15···N4viii | 3.071 (17) |
C12···H11i | 2.630 (18) | H15···C3xiii | 3.508 (19) |
C12···H19 | 2.543 (18) | H15···C24ix | 3.043 (19) |
C12···H19i | 3.099 (18) | H15···H2xiii | 2.73 (3) |
C12···H20 | 3.245 (19) | H15···H13viii | 2.94 (3) |
C12···H21 | 3.274 (18) | H16···N2ix | 3.431 (16) |
C12···H22 | 3.00 (2) | H16···C25ix | 3.544 (18) |
C12···H23 | 2.804 (15) | H16···H2xiii | 3.00 (3) |
C12···H23i | 3.324 (19) | H16···H17xiii | 2.93 (3) |
C13···H11i | 3.309 (18) | H17···N2ii | 2.87 (3) |
C13···H12 | 3.339 (14) | H17···N4viii | 3.15 (3) |
C13···H13 | 3.388 (16) | H17···C25ii | 3.27 (3) |
C13···H14 | 2.715 (16) | H17···H2xiii | 2.65 (3) |
C13···H16 | 3.165 (19) | H17···H16xiii | 2.93 (3) |
C13···H19i | 2.809 (18) | H17···H19xiv | 3.54 (3) |
C13···H23 | 2.842 (14) | H18···N1x | 3.39 (3) |
C13···H24 | 3.394 (15) | H18···N2ii | 3.55 (3) |
C14···H11 | 3.302 (14) | H18···N4viii | 3.29 (3) |
C14···H15 | 3.390 (19) | H18···C7x | 3.476 (17) |
C14···H16 | 2.82 (2) | H18···H6x | 2.64 (3) |
C14···H21 | 2.643 (15) | H18···H7x | 3.40 (3) |
C14···H22 | 2.905 (17) | H18···H8x | 3.42 (3) |
C15···H1 | 3.098 (18) | H18···H14viii | 3.58 (3) |
C15···H8 | 2.754 (18) | H19···N2vi | 3.477 (18) |
C15···H9 | 3.32 (3) | H19···N4iii | 2.955 (19) |
C15···H10 | 3.044 (19) | H19···C29iii | 3.228 (19) |
C15···H13 | 2.620 (19) | H19···H17xv | 3.54 (3) |
C15···H14 | 3.215 (17) | H20···N2vi | 2.838 (19) |
C16···H12 | 2.663 (17) | H20···N4iii | 2.99 (2) |
C16···H17 | 3.45 (3) | H20···C8xi | 3.532 (18) |
C16···H18 | 2.81 (2) | H20···C29iii | 3.22 (3) |
C16···H21 | 2.634 (14) | H20···H7xi | 2.55 (3) |
C16···H22 | 3.205 (15) | H21···N2ix | 2.777 (17) |
C17···H2 | 3.10 (3) | H21···C25ix | 3.142 (17) |
C17···H12 | 3.597 (17) | H21···H5ix | 3.36 (4) |
C17···H21 | 2.756 (15) | H22···N3iii | 2.663 (19) |
C18···H1 | 2.659 (18) | H22···C7ix | 3.26 (2) |
C18···H2 | 2.74 (2) | H22···C27 | 3.549 (18) |
C18···H12 | 3.556 (18) | H22···C28iii | 2.927 (19) |
C18···H13 | 2.78 (2) | H22···H4ix | 3.25 (3) |
C18···H14 | 3.449 (18) | H22···H5ix | 2.39 (4) |
C19···H9 | 2.574 (18) | H22···H6ix | 3.35 (4) |
C19···H10 | 3.277 (16) | H23···N3iii | 3.336 (19) |
C19···H11 | 2.610 (16) | H24···N2ix | 2.740 (17) |
C19···H11i | 3.005 (17) | H24···N3xvi | 3.334 (16) |
C19···H21i | 2.776 (17) | H24···C25ix | 3.508 (17) |
C19···H22i | 3.44 (2) | H24···H4ix | 2.95 (4) |
C20···H11 | 2.695 (17) | ||
C2—C1—C6 | 122.08 (13) | N4—C29—C26 | 162.91 (18) |
C1—C2—C3 | 118.44 (14) | N4—C29—C27 | 159.5 (2) |
C1—C2—C18 | 120.43 (13) | C26—C29—C27 | 37.62 (17) |
C3—C2—C18 | 121.03 (13) | C2—C1—H1 | 118.1 (11) |
C2—C3—C4 | 120.06 (13) | C6—C1—H1 | 119.8 (11) |
C3—C4—C5 | 120.49 (14) | C2—C3—H2 | 121.3 (13) |
C4—C5—C6 | 120.66 (15) | C4—C3—H2 | 118.6 (12) |
C1—C6—C5 | 118.04 (13) | C3—C4—H3 | 119.8 (12) |
C1—C6—C7 | 119.43 (14) | C5—C4—H3 | 119.7 (12) |
C5—C6—C7 | 122.39 (15) | C4—C5—H4 | 119.3 (12) |
C6—C7—C8 | 114.34 (15) | C6—C5—H4 | 120.1 (12) |
C7—C8—C9 | 116.32 (13) | C6—C7—H5 | 111.3 (15) |
C8—C9—C10 | 119.05 (14) | C6—C7—H6 | 111.8 (15) |
C9—C10—C11 | 120.79 (13) | C8—C7—H5 | 105.0 (19) |
C9—C10—C15 | 121.46 (11) | C8—C7—H6 | 109.9 (16) |
C11—C10—C15 | 117.74 (12) | H5—C7—H6 | 104 (3) |
C10—C11—C12 | 118.50 (13) | C7—C8—H7 | 109.4 (14) |
C10—C11—C19 | 123.07 (12) | C7—C8—H8 | 110.1 (12) |
C12—C11—C19 | 118.29 (10) | C9—C8—H7 | 106.1 (11) |
C11—C12—C13 | 123.50 (11) | C9—C8—H8 | 110.0 (10) |
C12—C13—C14 | 117.90 (12) | H7—C8—H8 | 104.2 (16) |
C12—C13—C20 | 120.57 (10) | C8—C9—H9 | 106.3 (12) |
C14—C13—C20 | 121.52 (12) | C8—C9—H10 | 109.4 (9) |
C13—C14—C15 | 118.34 (13) | C10—C9—H9 | 106.8 (11) |
C13—C14—C16 | 122.34 (12) | C10—C9—H10 | 108.3 (11) |
C15—C14—C16 | 119.33 (10) | H9—C9—H10 | 106.2 (17) |
C10—C15—C14 | 123.34 (11) | C11—C12—H11 | 117.0 (10) |
C14—C16—C17 | 116.14 (13) | C13—C12—H11 | 119.5 (10) |
C16—C17—C18 | 116.71 (12) | C10—C15—H12 | 118.4 (10) |
C2—C18—C17 | 113.70 (12) | C14—C15—H12 | 118.0 (10) |
C11—C19—C21i | 112.79 (12) | C14—C16—H13 | 110.5 (10) |
C13—C20—C21 | 116.02 (12) | C14—C16—H14 | 107.8 (9) |
C19i—C21—C20 | 113.53 (11) | C17—C16—H13 | 108.5 (11) |
C22ii—C22—C24 | 113.7 (7) | C17—C16—H14 | 110.1 (10) |
C22ii—C22—C25ii | 113.6 (6) | H13—C16—H14 | 103.0 (14) |
C24—C22—C25ii | 132.7 (6) | C16—C17—H15 | 105.0 (12) |
C23ii—C23—C24 | 118.44 (17) | C16—C17—H16 | 112.2 (11) |
C23ii—C23—C25 | 119.30 (15) | C18—C17—H15 | 110.0 (11) |
C24—C23—C25 | 122.26 (15) | C18—C17—H16 | 108.7 (12) |
N1—C24—C22 | 148.2 (4) | H15—C17—H16 | 103.3 (15) |
N1—C24—C23 | 174.27 (19) | C2—C18—H17 | 109.3 (14) |
C22—C24—C23 | 37.5 (4) | C2—C18—H18 | 109.4 (13) |
N2—C25—C22ii | 148.1 (3) | C17—C18—H17 | 107.9 (12) |
N2—C25—C23 | 174.49 (16) | C17—C18—H18 | 109.1 (13) |
C22ii—C25—C23 | 37.4 (3) | H17—C18—H18 | 107.2 (16) |
C26iii—C26—C27iii | 44.2 (3) | C11—C19—H19 | 107.6 (10) |
C26iii—C26—C28 | 116.0 (3) | C11—C19—H20 | 110.4 (11) |
C26iii—C26—C29 | 116.9 (3) | C21i—C19—H19 | 110.1 (11) |
C27iii—C26—C28 | 71.8 (3) | C21i—C19—H20 | 109.6 (12) |
C27iii—C26—C29 | 161.1 (3) | H19—C19—H20 | 106.1 (14) |
C28—C26—C29 | 127.10 (18) | C13—C20—H21 | 107.6 (9) |
C26iii—C27—C27iii | 44.5 (3) | C13—C20—H22 | 106.4 (10) |
C26iii—C27—C28iii | 69.9 (3) | C21—C20—H21 | 108.8 (9) |
C26iii—C27—C29 | 161.3 (4) | C21—C20—H22 | 110.0 (9) |
C27iii—C27—C28iii | 114.4 (3) | H21—C20—H22 | 107.8 (15) |
C27iii—C27—C29 | 116.8 (3) | C19i—C21—H23 | 109.4 (12) |
C28iii—C27—C29 | 128.8 (3) | C19i—C21—H24 | 109.3 (12) |
N3—C28—C26 | 163.7 (2) | C20—C21—H23 | 111.4 (9) |
N3—C28—C27iii | 157.9 (3) | C20—C21—H24 | 106.3 (9) |
C26—C28—C27iii | 38.33 (18) | H23—C21—H24 | 106.6 (13) |
C2—C1—C6—C5 | 5.5 (3) | C22ii—C22—C24—N1 | 179.6 (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—C25 | 1.8 (9) |
C6—C1—C2—C18 | 171.25 (13) | C22ii—C22—C25ii—N2ii | −178.7 (5) |
C1—C2—C3—C4 | 1.7 (2) | C22ii—C22—C25ii—C23ii | 0.7 (4) |
C1—C2—C18—C17 | −111.99 (14) | C25ii—C22—C22ii—C24ii | −1.8 (9) |
C3—C2—C18—C17 | 64.33 (19) | C24—C22—C25ii—N2ii | −1.0 (13) |
C18—C2—C3—C4 | −174.72 (13) | C24—C22—C25ii—C23ii | 178.4 (11) |
C2—C3—C4—C5 | 1.3 (3) | C25ii—C22—C24—N1 | 1.9 (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—C22 | 0.71 (12) |
C4—C5—C6—C7 | 173.19 (14) | C24—C23—C23ii—C25ii | 0.0 (3) |
C1—C6—C7—C8 | 61.87 (19) | C23ii—C23—C25—C22ii | 0.72 (12) |
C5—C6—C7—C8 | −113.71 (18) | C25—C23—C23ii—C24ii | −0.0 (3) |
C6—C7—C8—C9 | 60.3 (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—C11 | 151.51 (14) | C26iii—C26—C27iii—C27 | 0 (12936568) |
C8—C9—C10—C15 | −29.5 (2) | C26iii—C26—C27iii—C28 | −179.6 (4) |
C9—C10—C11—C12 | 179.26 (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—C14 | 173.81 (13) | C26iii—C26—C28—C27iii | 0.30 (17) |
C11—C10—C15—C14 | −7.2 (3) | C28—C26—C26iii—C27 | 179.6 (4) |
C15—C10—C11—C12 | 0.2 (2) | C28—C26—C26iii—C29iii | −0.6 (4) |
C15—C10—C11—C19 | 175.82 (12) | C26iii—C26—C29—C27 | −0.16 (17) |
C10—C11—C12—C13 | 6.5 (3) | C29—C26—C26iii—C27 | 0.2 (3) |
C10—C11—C19—C21i | −76.48 (16) | C29—C26—C26iii—C28iii | 0.6 (4) |
C12—C11—C19—C21i | 99.13 (14) | C28—C26—C27iii—C27 | 179.6 (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—C27iii | 179.6 (4) |
C11—C12—C13—C20 | 173.34 (13) | C26iii—C27—C27iii—C28 | −179.6 (5) |
C12—C13—C14—C15 | −0.6 (2) | C26iii—C27—C27iii—C29iii | 0.2 (4) |
C12—C13—C14—C16 | 179.13 (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—C21 | 155.60 (13) | C27iii—C27—C28iii—C26iii | 0.3 (2) |
C20—C13—C14—C15 | 179.77 (12) | C28iii—C27—C27iii—C26 | 179.6 (5) |
C20—C13—C14—C16 | −0.5 (3) | C28iii—C27—C27iii—C29iii | −0.2 (5) |
C13—C14—C15—C10 | 7.4 (3) | C27iii—C27—C29—N4 | −177.8 (5) |
C13—C14—C16—C17 | −78.71 (17) | C27iii—C27—C29—C26 | 0.2 (2) |
C15—C14—C16—C17 | 101.02 (14) | C29—C27—C27iii—C26 | −0.2 (3) |
C16—C14—C15—C10 | −172.37 (13) | C29—C27—C27iii—C28 | 0.2 (5) |
C14—C16—C17—C18 | −75.03 (13) | C28iii—C27—C29—N4 | 2.4 (9) |
C16—C17—C18—C2 | 69.70 (16) | C28iii—C27—C29—C26 | −179.6 (6) |
C11—C19—C21i—C20i | −122.71 (10) | C29—C27—C28iii—N3iii | 1.3 (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 formula | C42H48·2C6N4 |
Mr | 809.03 |
Crystal system, space group | Triclinic, 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) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.35 × 0.16 × 0.09 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | – |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 17470, 4775, 4141 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.178, 1.00 |
No. of reflections | 4775 |
No. of parameters | 394 |
H-atom treatment | Only 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).
N1—C24 | 1.1223 (19) | C13—C20 | 1.5178 (18) |
N2—C25 | 1.126 (3) | C14—C15 | 1.3997 (18) |
N3—C28 | 1.124 (2) | C14—C16 | 1.520 (2) |
N4—C29 | 1.113 (3) | C16—C17 | 1.547 (3) |
C1—C2 | 1.3873 (19) | C17—C18 | 1.540 (3) |
C1—C6 | 1.400 (3) | C19—C21i | 1.557 (3) |
C2—C3 | 1.4000 (19) | C20—C21 | 1.5323 (17) |
C2—C18 | 1.509 (3) | C22—C22ii | 1.333 (11) |
C3—C4 | 1.389 (3) | C22—C24 | 1.504 (7) |
C4—C5 | 1.386 (3) | C22—C25ii | 1.504 (8) |
C5—C6 | 1.391 (3) | C23—C23ii | 1.354 (3) |
C6—C7 | 1.510 (3) | C23—C24 | 1.454 (3) |
C7—C8 | 1.529 (3) | C23—C25 | 1.447 (3) |
C8—C9 | 1.517 (2) | C26—C26iii | 1.362 (4) |
C9—C10 | 1.5221 (19) | C26—C27iii | 0.972 (5) |
C10—C11 | 1.4037 (16) | C26—C28 | 1.472 (4) |
C10—C15 | 1.403 (2) | C26—C29 | 1.472 (4) |
C11—C12 | 1.3975 (19) | C27—C27iii | 1.356 (6) |
C11—C19 | 1.519 (2) | C27—C28iii | 1.488 (4) |
C12—C13 | 1.398 (2) | C27—C29 | 1.475 (4) |
C13—C14 | 1.4052 (16) | ||
C2—C1—C6 | 122.08 (13) | C19i—C21—C20 | 113.53 (11) |
C1—C2—C3 | 118.44 (14) | C22ii—C22—C24 | 113.7 (7) |
C1—C2—C18 | 120.43 (13) | C22ii—C22—C25ii | 113.6 (6) |
C3—C2—C18 | 121.03 (13) | C24—C22—C25ii | 132.7 (6) |
C2—C3—C4 | 120.06 (13) | C23ii—C23—C24 | 118.44 (17) |
C3—C4—C5 | 120.49 (14) | C23ii—C23—C25 | 119.30 (15) |
C4—C5—C6 | 120.66 (15) | C24—C23—C25 | 122.26 (15) |
C1—C6—C5 | 118.04 (13) | N1—C24—C22 | 148.2 (4) |
C1—C6—C7 | 119.43 (14) | N1—C24—C23 | 174.27 (19) |
C5—C6—C7 | 122.39 (15) | C22—C24—C23 | 37.5 (4) |
C6—C7—C8 | 114.34 (15) | N2—C25—C22ii | 148.1 (3) |
C7—C8—C9 | 116.32 (13) | N2—C25—C23 | 174.49 (16) |
C8—C9—C10 | 119.05 (14) | C22ii—C25—C23 | 37.4 (3) |
C9—C10—C11 | 120.79 (13) | C26iii—C26—C27iii | 44.2 (3) |
C9—C10—C15 | 121.46 (11) | C26iii—C26—C28 | 116.0 (3) |
C11—C10—C15 | 117.74 (12) | C26iii—C26—C29 | 116.9 (3) |
C10—C11—C12 | 118.50 (13) | C27iii—C26—C28 | 71.8 (3) |
C10—C11—C19 | 123.07 (12) | C27iii—C26—C29 | 161.1 (3) |
C12—C11—C19 | 118.29 (10) | C28—C26—C29 | 127.10 (18) |
C11—C12—C13 | 123.50 (11) | C26iii—C27—C27iii | 44.5 (3) |
C12—C13—C14 | 117.90 (12) | C26iii—C27—C28iii | 69.9 (3) |
C12—C13—C20 | 120.57 (10) | C26iii—C27—C29 | 161.3 (4) |
C14—C13—C20 | 121.52 (12) | C27iii—C27—C28iii | 114.4 (3) |
C13—C14—C15 | 118.34 (13) | C27iii—C27—C29 | 116.8 (3) |
C13—C14—C16 | 122.34 (12) | C28iii—C27—C29 | 128.8 (3) |
C15—C14—C16 | 119.33 (10) | N3—C28—C26 | 163.7 (2) |
C10—C15—C14 | 123.34 (11) | N3—C28—C27iii | 157.9 (3) |
C14—C16—C17 | 116.14 (13) | C26—C28—C27iii | 38.33 (18) |
C16—C17—C18 | 116.71 (12) | N4—C29—C26 | 162.91 (18) |
C2—C18—C17 | 113.70 (12) | N4—C29—C27 | 159.5 (2) |
C11—C19—C21i | 112.79 (12) | C26—C29—C27 | 37.62 (17) |
C13—C20—C21 | 116.02 (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
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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.