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COMMUNICATIONS
ISSN: 2056-9890

9-[3-(Carbazol-9-yl)-5-methyl­phen­yl]carbazole

aDepartment of Chemistry, Konyang University, Nonsan 320-711, Republic of Korea
*Correspondence e-mail: jylee@konyang.ac.kr, jylee@konyang.ac.kr

(Received 15 March 2013; accepted 29 April 2013; online 4 May 2013)

The title compound, C31H22N2, crystallizes with two symmetry-independent mol­ecules in the asymmetric unit. The mol­ecules have slightly different conformations, the dihedral angles between the central phenyl ring and the carbazolyl groups being 56.29 (4) and 59.57 (4)° in one mol­ecule and 48.71 (4) and 65.47 (4)° in the other. In the crystal, mol­ecules are linked by weak C—H⋯π and ππ [centroid–centroid distances = 3.7698 (10), 3.8292 (9), 3.9429 (10) and 3.9431 (10) Å].

Related literature

For the preparation of the title compound, see: Kwon et al. (2007[Kwon, T.-H., Kim, M. K., Kwon, J., Shin, D.-Y., Park, S. J., Lee, C.-L., Kim, J.-J. & Hong, J.-I. (2007). Chem. Mater. 19, 3673-3680.]). For the structure of the related compound 1,3-bis­(carbazol-9-yl)benzene, see: Sun et al. (2006[Sun, Y.-H., Zhu, X.-H., Chen, Z., Zhang, Y. & Cao, Y. (2006). J. Org. Chem. 71, 6281-6284.]).

[Scheme 1]

Experimental

Crystal data
  • C31H22N2

  • Mr = 422.51

  • Monoclinic, P 21 /n

  • a = 9.2503 (1) Å

  • b = 29.3854 (4) Å

  • c = 16.2616 (2) Å

  • β = 96.901 (1)°

  • V = 4388.27 (9) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 173 K

  • 0.26 × 0.23 × 0.22 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.981, Tmax = 0.984

  • 42985 measured reflections

  • 10834 independent reflections

  • 7284 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.117

  • S = 1.03

  • 10834 reflections

  • 598 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
C—H⋯π (Å, °)

Cg1, Cg3—Cg6 and Cg9 are the centroids of the C44–C49, C7–C12, C56–C61, C1–C6, C19–C24 and C32–C37 benzene rings while Cg2, Cg7 and Cg8 are the centroids of the N4/C50/C55/C56/C61, N2/C19/C24/C25/C30 and N3/C32/C37/C38/C43 pyrrole rings.

C—H⋯π C—H H⋯Cg CCg C—H⋯Cg
C9—H9ACg1i 0.95 2.96 3.776 (2) 145
C5—H5ACg2ii 0.95 2.77 3.6969 (19) 165
C53—H53ACg3iii 0.95 2.76 3.5983 (19) 148
C8—H8ACg4ii 0.95 2.81 3.7122 (19) 160
C49—H49ACg5 0.95 2.98 3.8654 (16) 156
C57—H57ACg6iv 0.95 2.85 3.3776 (17) 117
C58—H58ACg7iv 0.95 2.88 3.3749 (18) 114
C59—H59ACg8v 0.95 2.66 3.5084 (18) 149
C60—H60ACg9v 0.95 2.74 3.5180 (17) 140
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) x, y, z-1; (iv) -x, -y+1, -z+1; (v) x-1, y, z.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2006[Bruker (2006). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound, 5-mCP (systematic name: 5-methyl-N,N-dicarbazolyl-1,3-benzene), had been shown to be better for fluorescent blue light-emitting dopants (Kwon et al., 2007). However, its crystal structure has not been reported yet, which motivated this study.

The title structure (Fig. 1) is composed of two symmetry independent molecules each of which has a different conformation. The conformers can be compared by Figs. 2 and 3. Specifically, the difference between the conformers is manifested by interplanar angles between the central phenyl fragment and the carbazolyl groups. These angles (see Fig. 1) are equal to 56.29 (4) ° (A—B), 59.57 (4) ° (A—C), 48.71 (4) ° (D—E) and 65.47 (4)° (D—F). All the bond lengths and the bond angles are normal and comparable to those observed in a similar structure of m-CP = 1,3-bis(carbazol-9-yl)benzene (Sun et al., 2006).

In the crystal structure, the molecules are linked by weak intermolecular C—H···π-electron ring interactions - see Fig. 4 and Table 1. In addition, there are also present π-electron···π-electron ring interactions in the structure. Their overview is given in Table 2 and also shown in Fig. 4.

Related literature top

For the preparation of the title compound, see: Kwon et al. (2007). For the structure of the related compound 1,3-bis(carbazol-9-yl)benzene, see: Sun et al. (2006).

Experimental top

The title compound was prepared by the reaction of carbazole with 1,3-dibromo-5-methylbenzene in toluene according to a method reported by Kwon et al. (2007). Single crystals of the title compound for X-ray analysis were obtained by slow evaporation of the CH2Cl2 solution. The single crystals were block-like (0.4×0.2×0.2 mm) and colourless.

Refinement top

All H atoms were discernible in the difference electron-density map. However, they were situated in idealized positions and refined with the following constraints: C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for aryl H atoms, and C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms. The methyl groups were allowed to rotate about the C—Cmethyl bonds using the function AFIX 137 of SHELXL97 (Sheldrick, 2008).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2006); data reduction: SAINT-Plus (Bruker, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The title molecules with the atom-numbering scheme and assigned labels to the rings (see text). The displacement ellipsoids are drawn at the 50% probability level. The H atoms are presented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. The first conformer. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are presented as small spheres of arbitrary radius.
[Figure 3] Fig. 3. The second conformer. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are presented as small spheres of arbitrary radius.
[Figure 4] Fig. 4. A view of the C—H···π interactions and π-electron ··· π-electron ring interactions (dotted lines) in the crystal structure of the title compound. Symmetry codes: (i) x - 1/2, -y + 3/2, z + 1/2; (ii) x + 1/2, -y + 3/2, z + 1/2; (iii) x, y, z - 1; (iv) -x, -y + 1, -z + 1; (v) x - 1, y, z; (vi) -x + 1, -y + 1, -z + 1; (vii) x + 3/2, -y + 3/2, z + 5/2.
9-[3-(Carbazol-9-yl)-5-methylphenyl]carbazole top
Crystal data top
C31H22N2F(000) = 1776
Mr = 422.51Dx = 1.279 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8960 reflections
a = 9.2503 (1) Åθ = 2.3–25.3°
b = 29.3854 (4) ŵ = 0.08 mm1
c = 16.2616 (2) ÅT = 173 K
β = 96.901 (1)°Block, colourless
V = 4388.27 (9) Å30.26 × 0.23 × 0.22 mm
Z = 8
Data collection top
Bruker APEXII CCD
diffractometer
10834 independent reflections
Radiation source: fine-focus sealed tube7284 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ϕ and ω scansθmax = 28.3°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1112
Tmin = 0.981, Tmax = 0.984k = 3933
42985 measured reflectionsl = 2121
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0411P)2 + 1.3445P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
10834 reflectionsΔρmax = 0.26 e Å3
598 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
174 constraintsExtinction coefficient: 0.0025 (3)
Primary atom site location: structure-invariant direct methods
Crystal data top
C31H22N2V = 4388.27 (9) Å3
Mr = 422.51Z = 8
Monoclinic, P21/nMo Kα radiation
a = 9.2503 (1) ŵ = 0.08 mm1
b = 29.3854 (4) ÅT = 173 K
c = 16.2616 (2) Å0.26 × 0.23 × 0.22 mm
β = 96.901 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
10834 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
7284 reflections with I > 2σ(I)
Tmin = 0.981, Tmax = 0.984Rint = 0.041
42985 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.03Δρmax = 0.26 e Å3
10834 reflectionsΔρmin = 0.22 e Å3
598 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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
N10.27690 (14)0.62649 (4)0.76286 (8)0.0290 (3)
N20.33297 (14)0.47722 (4)0.89106 (8)0.0275 (3)
N30.57996 (13)0.61483 (4)0.44472 (8)0.0274 (3)
N40.16834 (14)0.66661 (4)0.25357 (8)0.0279 (3)
C10.41194 (17)0.64001 (5)0.74124 (9)0.0271 (4)
C20.52539 (18)0.61396 (6)0.71889 (10)0.0329 (4)
H2A0.52010.58170.71810.039*
C30.64689 (19)0.63649 (7)0.69772 (10)0.0385 (4)
H3A0.72560.61930.68140.046*
C40.6567 (2)0.68386 (7)0.69976 (11)0.0421 (5)
H4A0.74170.69840.68520.051*
C50.5443 (2)0.70945 (6)0.72263 (10)0.0384 (4)
H5A0.55120.74170.72410.046*
C60.41973 (18)0.68787 (5)0.74376 (9)0.0306 (4)
C70.28475 (19)0.70389 (6)0.76935 (10)0.0322 (4)
C80.2317 (2)0.74691 (6)0.78619 (11)0.0431 (5)
H8A0.28780.77340.77930.052*
C90.0967 (2)0.75024 (7)0.81284 (11)0.0493 (5)
H9A0.06060.77930.82580.059*
C100.0120 (2)0.71195 (7)0.82116 (11)0.0468 (5)
H10A0.08200.71540.83820.056*
C110.06163 (19)0.66884 (6)0.80515 (11)0.0385 (4)
H11A0.00380.64260.81140.046*
C120.19901 (18)0.66530 (5)0.77966 (10)0.0306 (4)
C130.22740 (16)0.58089 (5)0.77080 (9)0.0267 (3)
C140.09856 (17)0.56694 (6)0.72562 (10)0.0315 (4)
H14A0.04480.58770.68900.038*
C150.04736 (17)0.52304 (6)0.73321 (10)0.0334 (4)
C160.12611 (17)0.49316 (6)0.78761 (10)0.0309 (4)
H16A0.09220.46290.79330.037*
C170.25452 (16)0.50739 (5)0.83373 (9)0.0267 (3)
C180.30585 (16)0.55118 (5)0.82526 (9)0.0258 (3)
H18A0.39400.56080.85650.031*
C190.27761 (17)0.45455 (5)0.95570 (9)0.0267 (4)
C200.14002 (18)0.45643 (6)0.98060 (10)0.0341 (4)
H20A0.06600.47510.95260.041*
C210.1141 (2)0.43014 (7)1.04771 (11)0.0434 (5)
H21A0.02080.43101.06650.052*
C220.2218 (2)0.40240 (7)1.08835 (11)0.0460 (5)
H22A0.20040.38441.13380.055*
C230.35877 (19)0.40069 (6)1.06370 (10)0.0373 (4)
H23A0.43170.38161.09170.045*
C240.38880 (17)0.42728 (5)0.99720 (9)0.0283 (4)
C250.51718 (17)0.43418 (5)0.95646 (10)0.0275 (4)
C260.65750 (18)0.41636 (6)0.96810 (11)0.0337 (4)
H26A0.68500.39551.01180.040*
C270.75564 (19)0.42934 (6)0.91567 (12)0.0404 (4)
H27A0.85170.41730.92320.048*
C280.7160 (2)0.45993 (7)0.85166 (12)0.0464 (5)
H28A0.78600.46850.81630.056*
C290.57758 (19)0.47825 (6)0.83807 (11)0.0391 (4)
H29A0.55110.49890.79390.047*
C300.47897 (17)0.46520 (5)0.89147 (10)0.0285 (4)
C310.0906 (2)0.50771 (8)0.68137 (13)0.0543 (6)
H31A0.09600.52160.62630.081*
H31B0.17520.51710.70820.081*
H31C0.09010.47450.67610.081*
C320.71967 (16)0.62901 (5)0.47688 (9)0.0268 (3)
C330.77012 (18)0.67215 (6)0.49994 (10)0.0318 (4)
H33A0.70710.69780.49530.038*
C340.91550 (18)0.67640 (6)0.52998 (11)0.0368 (4)
H34A0.95220.70550.54710.044*
C351.01002 (18)0.63939 (6)0.53595 (11)0.0378 (4)
H35A1.10940.64350.55730.045*
C360.95993 (17)0.59695 (6)0.51104 (10)0.0341 (4)
H36A1.02470.57170.51410.041*
C370.81306 (17)0.59115 (5)0.48111 (9)0.0283 (4)
C380.72705 (17)0.55249 (6)0.45035 (9)0.0286 (4)
C390.75808 (19)0.50671 (6)0.44074 (11)0.0362 (4)
H39A0.85490.49580.45340.043*
C400.6475 (2)0.47731 (6)0.41274 (11)0.0379 (4)
H40A0.66790.44590.40600.045*
C410.50542 (19)0.49329 (6)0.39419 (10)0.0351 (4)
H41A0.43000.47230.37610.042*
C420.47147 (18)0.53863 (6)0.40137 (10)0.0318 (4)
H42A0.37460.54930.38790.038*
C430.58400 (17)0.56821 (5)0.42906 (9)0.0268 (3)
C440.45648 (16)0.64348 (5)0.42645 (9)0.0251 (3)
C450.37372 (16)0.64064 (5)0.34928 (9)0.0268 (3)
H45A0.39850.61950.30900.032*
C460.25485 (16)0.66907 (5)0.33223 (9)0.0259 (3)
C470.22033 (17)0.70061 (5)0.39003 (10)0.0282 (4)
H47A0.13940.72030.37690.034*
C480.30322 (16)0.70377 (5)0.46735 (10)0.0278 (4)
C490.41995 (16)0.67422 (5)0.48516 (9)0.0276 (4)
H49A0.47540.67510.53820.033*
C500.21311 (17)0.67856 (5)0.17760 (9)0.0264 (3)
C510.34967 (18)0.69130 (6)0.15945 (10)0.0334 (4)
H51A0.43020.69310.20150.040*
C520.3645 (2)0.70125 (6)0.07790 (11)0.0378 (4)
H52A0.45740.70970.06350.045*
C530.2460 (2)0.69919 (6)0.01607 (11)0.0378 (4)
H53A0.25910.70670.03940.045*
C540.11100 (19)0.68644 (6)0.03460 (10)0.0331 (4)
H54A0.03090.68490.00780.040*
C550.09246 (17)0.67578 (5)0.11612 (9)0.0271 (4)
C560.02945 (17)0.66053 (5)0.15654 (9)0.0251 (3)
C570.17423 (17)0.64988 (5)0.12858 (10)0.0303 (4)
H57A0.21040.65310.07170.036*
C580.26369 (18)0.63463 (6)0.18442 (10)0.0328 (4)
H58A0.36250.62760.16590.039*
C590.21114 (18)0.62944 (6)0.26783 (10)0.0320 (4)
H59A0.27470.61850.30510.038*
C600.06856 (17)0.63980 (5)0.29759 (10)0.0296 (4)
H60A0.03330.63640.35460.036*
C610.02111 (16)0.65531 (5)0.24095 (9)0.0252 (3)
C620.26782 (18)0.73838 (6)0.53012 (11)0.0387 (4)
H62A0.35740.75380.55350.058*
H62B0.22370.72310.57450.058*
H62C0.19940.76080.50320.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0300 (7)0.0231 (7)0.0347 (8)0.0001 (6)0.0066 (6)0.0044 (6)
N20.0270 (7)0.0256 (7)0.0297 (7)0.0013 (6)0.0029 (5)0.0063 (6)
N30.0253 (7)0.0278 (7)0.0281 (7)0.0024 (6)0.0006 (5)0.0001 (6)
N40.0260 (7)0.0341 (8)0.0226 (7)0.0002 (6)0.0019 (5)0.0016 (6)
C10.0302 (8)0.0262 (9)0.0244 (8)0.0037 (7)0.0012 (6)0.0026 (6)
C20.0336 (9)0.0333 (10)0.0314 (9)0.0012 (7)0.0027 (7)0.0000 (7)
C30.0318 (9)0.0527 (12)0.0314 (9)0.0029 (8)0.0053 (7)0.0001 (8)
C40.0402 (11)0.0546 (13)0.0311 (9)0.0194 (9)0.0026 (8)0.0039 (9)
C50.0513 (11)0.0323 (10)0.0304 (9)0.0164 (9)0.0001 (8)0.0034 (7)
C60.0412 (10)0.0268 (9)0.0224 (8)0.0057 (7)0.0015 (7)0.0034 (7)
C70.0435 (10)0.0273 (9)0.0245 (8)0.0028 (8)0.0009 (7)0.0045 (7)
C80.0641 (13)0.0278 (10)0.0349 (10)0.0074 (9)0.0047 (9)0.0029 (8)
C90.0687 (14)0.0404 (12)0.0359 (10)0.0258 (11)0.0058 (10)0.0023 (9)
C100.0467 (11)0.0603 (14)0.0322 (10)0.0242 (10)0.0006 (8)0.0010 (9)
C110.0357 (10)0.0443 (11)0.0356 (10)0.0075 (8)0.0045 (8)0.0041 (8)
C120.0377 (9)0.0279 (9)0.0253 (8)0.0069 (7)0.0008 (7)0.0048 (7)
C130.0274 (8)0.0253 (8)0.0279 (8)0.0028 (6)0.0057 (6)0.0018 (7)
C140.0299 (9)0.0352 (10)0.0286 (8)0.0011 (7)0.0006 (7)0.0104 (7)
C150.0284 (9)0.0415 (10)0.0294 (9)0.0083 (7)0.0003 (7)0.0059 (7)
C160.0319 (9)0.0298 (9)0.0310 (9)0.0087 (7)0.0036 (7)0.0032 (7)
C170.0273 (8)0.0267 (9)0.0258 (8)0.0000 (7)0.0019 (6)0.0024 (6)
C180.0238 (8)0.0271 (9)0.0261 (8)0.0031 (6)0.0013 (6)0.0005 (7)
C190.0295 (8)0.0227 (8)0.0274 (8)0.0066 (6)0.0008 (6)0.0014 (6)
C200.0311 (9)0.0378 (10)0.0330 (9)0.0050 (7)0.0017 (7)0.0021 (8)
C210.0337 (10)0.0593 (13)0.0376 (10)0.0125 (9)0.0054 (8)0.0075 (9)
C220.0421 (11)0.0604 (13)0.0337 (10)0.0196 (9)0.0027 (8)0.0184 (9)
C230.0363 (10)0.0376 (10)0.0346 (9)0.0121 (8)0.0096 (8)0.0103 (8)
C240.0304 (8)0.0247 (9)0.0283 (8)0.0079 (7)0.0032 (7)0.0011 (7)
C250.0279 (8)0.0236 (8)0.0294 (8)0.0042 (7)0.0026 (7)0.0011 (7)
C260.0350 (9)0.0256 (9)0.0380 (9)0.0003 (7)0.0058 (8)0.0006 (7)
C270.0313 (9)0.0391 (11)0.0499 (11)0.0053 (8)0.0009 (8)0.0043 (9)
C280.0362 (10)0.0573 (13)0.0480 (11)0.0026 (9)0.0148 (9)0.0081 (10)
C290.0369 (10)0.0436 (11)0.0376 (10)0.0027 (8)0.0083 (8)0.0111 (8)
C300.0279 (8)0.0264 (9)0.0304 (8)0.0023 (7)0.0002 (7)0.0004 (7)
C310.0431 (11)0.0686 (14)0.0465 (11)0.0238 (10)0.0141 (9)0.0196 (10)
C320.0250 (8)0.0328 (9)0.0220 (8)0.0004 (7)0.0005 (6)0.0030 (7)
C330.0295 (9)0.0317 (9)0.0337 (9)0.0019 (7)0.0018 (7)0.0015 (7)
C340.0322 (9)0.0358 (10)0.0414 (10)0.0052 (8)0.0003 (8)0.0024 (8)
C350.0259 (9)0.0459 (11)0.0397 (10)0.0045 (8)0.0031 (7)0.0110 (8)
C360.0279 (9)0.0378 (10)0.0355 (9)0.0058 (7)0.0005 (7)0.0120 (8)
C370.0292 (8)0.0320 (9)0.0236 (8)0.0033 (7)0.0023 (6)0.0064 (7)
C380.0301 (9)0.0316 (9)0.0239 (8)0.0029 (7)0.0024 (6)0.0042 (7)
C390.0347 (9)0.0350 (10)0.0383 (10)0.0081 (8)0.0021 (8)0.0035 (8)
C400.0491 (11)0.0285 (10)0.0359 (10)0.0065 (8)0.0043 (8)0.0017 (8)
C410.0411 (10)0.0327 (10)0.0308 (9)0.0033 (8)0.0010 (7)0.0039 (7)
C420.0313 (9)0.0348 (10)0.0288 (8)0.0021 (7)0.0006 (7)0.0023 (7)
C430.0306 (8)0.0287 (9)0.0208 (7)0.0024 (7)0.0022 (6)0.0009 (6)
C440.0223 (8)0.0262 (8)0.0263 (8)0.0006 (6)0.0003 (6)0.0027 (6)
C450.0293 (8)0.0261 (9)0.0247 (8)0.0008 (7)0.0025 (6)0.0021 (6)
C460.0244 (8)0.0282 (9)0.0241 (8)0.0019 (6)0.0012 (6)0.0020 (6)
C470.0232 (8)0.0285 (9)0.0321 (9)0.0025 (7)0.0002 (6)0.0000 (7)
C480.0249 (8)0.0291 (9)0.0295 (8)0.0023 (7)0.0033 (6)0.0028 (7)
C490.0257 (8)0.0322 (9)0.0240 (8)0.0018 (7)0.0009 (6)0.0005 (7)
C500.0317 (9)0.0241 (8)0.0230 (8)0.0017 (7)0.0014 (6)0.0008 (6)
C510.0323 (9)0.0338 (10)0.0334 (9)0.0012 (7)0.0009 (7)0.0008 (7)
C520.0396 (10)0.0344 (10)0.0407 (10)0.0033 (8)0.0106 (8)0.0033 (8)
C530.0478 (11)0.0384 (10)0.0283 (9)0.0031 (8)0.0085 (8)0.0066 (8)
C540.0385 (10)0.0347 (10)0.0250 (8)0.0046 (8)0.0003 (7)0.0029 (7)
C550.0316 (9)0.0228 (8)0.0262 (8)0.0033 (7)0.0006 (7)0.0000 (6)
C560.0302 (8)0.0198 (8)0.0242 (8)0.0033 (6)0.0008 (6)0.0003 (6)
C570.0324 (9)0.0279 (9)0.0285 (8)0.0017 (7)0.0049 (7)0.0016 (7)
C580.0279 (8)0.0318 (9)0.0369 (9)0.0023 (7)0.0027 (7)0.0047 (7)
C590.0330 (9)0.0314 (9)0.0322 (9)0.0032 (7)0.0067 (7)0.0001 (7)
C600.0338 (9)0.0297 (9)0.0246 (8)0.0003 (7)0.0005 (7)0.0018 (7)
C610.0266 (8)0.0229 (8)0.0249 (8)0.0025 (6)0.0012 (6)0.0003 (6)
C620.0311 (9)0.0440 (11)0.0402 (10)0.0024 (8)0.0007 (8)0.0143 (8)
Geometric parameters (Å, º) top
N1—C121.393 (2)C28—H28A0.9500
N1—C11.396 (2)C29—C301.387 (2)
N1—C131.427 (2)C29—H29A0.9500
N2—C191.393 (2)C31—H31A0.9800
N2—C301.395 (2)C31—H31B0.9800
N2—C171.4210 (19)C31—H31C0.9800
N3—C431.395 (2)C32—C331.387 (2)
N3—C321.3981 (19)C32—C371.405 (2)
N3—C441.4213 (19)C33—C341.380 (2)
N4—C611.3928 (19)C33—H33A0.9500
N4—C501.394 (2)C34—C351.392 (2)
N4—C461.4269 (18)C34—H34A0.9500
C1—C21.382 (2)C35—C361.374 (2)
C1—C61.409 (2)C35—H35A0.9500
C2—C31.383 (2)C36—C371.397 (2)
C2—H2A0.9500C36—H36A0.9500
C3—C41.395 (3)C37—C381.442 (2)
C3—H3A0.9500C38—C391.388 (2)
C4—C51.370 (3)C38—C431.405 (2)
C4—H4A0.9500C39—C401.374 (2)
C5—C61.394 (2)C39—H39A0.9500
C5—H5A0.9500C40—C411.394 (2)
C6—C71.442 (2)C40—H40A0.9500
C7—C81.395 (2)C41—C421.377 (2)
C7—C121.405 (2)C41—H41A0.9500
C8—C91.374 (3)C42—C431.389 (2)
C8—H8A0.9500C42—H42A0.9500
C9—C101.387 (3)C44—C491.385 (2)
C9—H9A0.9500C44—C451.392 (2)
C10—C111.383 (3)C45—C461.382 (2)
C10—H10A0.9500C45—H45A0.9500
C11—C121.387 (2)C46—C471.384 (2)
C11—H11A0.9500C47—C481.395 (2)
C13—C141.385 (2)C47—H47A0.9500
C13—C181.385 (2)C48—C491.389 (2)
C14—C151.385 (2)C48—C621.505 (2)
C14—H14A0.9500C49—H49A0.9500
C15—C161.389 (2)C50—C511.383 (2)
C15—C311.511 (2)C50—C551.408 (2)
C16—C171.391 (2)C51—C521.381 (2)
C16—H16A0.9500C51—H51A0.9500
C17—C181.384 (2)C52—C531.397 (2)
C18—H18A0.9500C52—H52A0.9500
C19—C201.382 (2)C53—C541.372 (2)
C19—C241.410 (2)C53—H53A0.9500
C20—C211.381 (2)C54—C551.393 (2)
C20—H20A0.9500C54—H54A0.9500
C21—C221.391 (3)C55—C561.443 (2)
C21—H21A0.9500C56—C571.397 (2)
C22—C231.375 (3)C56—C611.404 (2)
C22—H22A0.9500C57—C581.375 (2)
C23—C241.389 (2)C57—H57A0.9500
C23—H23A0.9500C58—C591.393 (2)
C24—C251.442 (2)C58—H58A0.9500
C25—C261.391 (2)C59—C601.383 (2)
C25—C301.408 (2)C59—H59A0.9500
C26—C271.372 (3)C60—C611.388 (2)
C26—H26A0.9500C60—H60A0.9500
C27—C281.391 (3)C62—H62A0.9800
C27—H27A0.9500C62—H62B0.9800
C28—C291.382 (2)C62—H62C0.9800
C12—N1—C1108.42 (13)C15—C31—H31A109.5
C12—N1—C13124.87 (14)C15—C31—H31B109.5
C1—N1—C13126.64 (13)H31A—C31—H31B109.5
C19—N2—C30108.58 (12)C15—C31—H31C109.5
C19—N2—C17126.05 (13)H31A—C31—H31C109.5
C30—N2—C17125.37 (13)H31B—C31—H31C109.5
C43—N3—C32108.49 (12)C33—C32—N3129.74 (14)
C43—N3—C44125.60 (12)C33—C32—C37121.70 (14)
C32—N3—C44125.82 (13)N3—C32—C37108.53 (13)
C61—N4—C50108.59 (12)C34—C33—C32117.41 (15)
C61—N4—C46125.26 (13)C34—C33—H33A121.3
C50—N4—C46125.96 (13)C32—C33—H33A121.3
C2—C1—N1129.75 (15)C33—C34—C35122.09 (16)
C2—C1—C6121.52 (15)C33—C34—H34A119.0
N1—C1—C6108.73 (14)C35—C34—H34A119.0
C1—C2—C3117.75 (16)C36—C35—C34120.13 (15)
C1—C2—H2A121.1C36—C35—H35A119.9
C3—C2—H2A121.1C34—C35—H35A119.9
C2—C3—C4121.60 (17)C35—C36—C37119.51 (16)
C2—C3—H3A119.2C35—C36—H36A120.2
C4—C3—H3A119.2C37—C36—H36A120.2
C5—C4—C3120.33 (17)C36—C37—C32119.13 (15)
C5—C4—H4A119.8C36—C37—C38133.62 (15)
C3—C4—H4A119.8C32—C37—C38107.24 (13)
C4—C5—C6119.59 (17)C39—C38—C43119.49 (15)
C4—C5—H5A120.2C39—C38—C37133.61 (15)
C6—C5—H5A120.2C43—C38—C37106.89 (14)
C5—C6—C1119.20 (16)C40—C39—C38119.39 (16)
C5—C6—C7133.86 (16)C40—C39—H39A120.3
C1—C6—C7106.94 (14)C38—C39—H39A120.3
C8—C7—C12119.39 (17)C39—C40—C41120.32 (16)
C8—C7—C6133.62 (17)C39—C40—H40A119.8
C12—C7—C6106.96 (14)C41—C40—H40A119.8
C9—C8—C7118.77 (18)C42—C41—C40121.75 (16)
C9—C8—H8A120.6C42—C41—H41A119.1
C7—C8—H8A120.6C40—C41—H41A119.1
C8—C9—C10121.21 (18)C41—C42—C43117.60 (15)
C8—C9—H9A119.4C41—C42—H42A121.2
C10—C9—H9A119.4C43—C42—H42A121.2
C11—C10—C9121.41 (19)C42—C43—N3129.67 (14)
C11—C10—H10A119.3C42—C43—C38121.41 (15)
C9—C10—H10A119.3N3—C43—C38108.85 (13)
C10—C11—C12117.48 (18)C49—C44—C45120.48 (14)
C10—C11—H11A121.3C49—C44—N3119.91 (13)
C12—C11—H11A121.3C45—C44—N3119.61 (14)
C11—C12—N1129.33 (16)C46—C45—C44118.86 (14)
C11—C12—C7121.71 (16)C46—C45—H45A120.6
N1—C12—C7108.94 (15)C44—C45—H45A120.6
C14—C13—C18120.26 (14)C45—C46—C47120.75 (14)
C14—C13—N1119.67 (14)C45—C46—N4119.74 (14)
C18—C13—N1120.04 (13)C47—C46—N4119.50 (14)
C15—C14—C13120.68 (15)C46—C47—C48120.66 (14)
C15—C14—H14A119.7C46—C47—H47A119.7
C13—C14—H14A119.7C48—C47—H47A119.7
C14—C15—C16119.13 (14)C49—C48—C47118.40 (14)
C14—C15—C31120.20 (15)C49—C48—C62120.55 (14)
C16—C15—C31120.65 (16)C47—C48—C62121.04 (14)
C15—C16—C17120.12 (15)C44—C49—C48120.79 (14)
C15—C16—H16A119.9C44—C49—H49A119.6
C17—C16—H16A119.9C48—C49—H49A119.6
C18—C17—C16120.46 (14)C51—C50—N4129.30 (14)
C18—C17—N2119.41 (13)C51—C50—C55122.04 (14)
C16—C17—N2120.12 (14)N4—C50—C55108.66 (13)
C17—C18—C13119.33 (14)C52—C51—C50117.46 (15)
C17—C18—H18A120.3C52—C51—H51A121.3
C13—C18—H18A120.3C50—C51—H51A121.3
C20—C19—N2129.55 (14)C51—C52—C53121.46 (17)
C20—C19—C24121.80 (15)C51—C52—H52A119.3
N2—C19—C24108.65 (14)C53—C52—H52A119.3
C21—C20—C19117.52 (16)C54—C53—C52120.69 (16)
C21—C20—H20A121.2C54—C53—H53A119.7
C19—C20—H20A121.2C52—C53—H53A119.7
C20—C21—C22121.40 (17)C53—C54—C55119.34 (15)
C20—C21—H21A119.3C53—C54—H54A120.3
C22—C21—H21A119.3C55—C54—H54A120.3
C23—C22—C21121.01 (16)C54—C55—C50119.01 (15)
C23—C22—H22A119.5C54—C55—C56134.08 (14)
C21—C22—H22A119.5C50—C55—C56106.89 (13)
C22—C23—C24118.94 (16)C57—C56—C61119.16 (15)
C22—C23—H23A120.5C57—C56—C55133.81 (14)
C24—C23—H23A120.5C61—C56—C55107.00 (13)
C23—C24—C19119.31 (15)C58—C57—C56119.17 (15)
C23—C24—C25133.59 (15)C58—C57—H57A120.4
C19—C24—C25107.09 (13)C56—C57—H57A120.4
C26—C25—C30119.45 (15)C57—C58—C59120.76 (15)
C26—C25—C24133.71 (15)C57—C58—H58A119.6
C30—C25—C24106.83 (13)C59—C58—H58A119.6
C27—C26—C25119.14 (16)C60—C59—C58121.53 (16)
C27—C26—H26A120.4C60—C59—H59A119.2
C25—C26—H26A120.4C58—C59—H59A119.2
C26—C27—C28120.67 (16)C59—C60—C61117.44 (14)
C26—C27—H27A119.7C59—C60—H60A121.3
C28—C27—H27A119.7C61—C60—H60A121.3
C29—C28—C27121.84 (18)C60—C61—N4129.20 (13)
C29—C28—H28A119.1C60—C61—C56121.93 (14)
C27—C28—H28A119.1N4—C61—C56108.84 (14)
C28—C29—C30117.28 (16)C48—C62—H62A109.5
C28—C29—H29A121.4C48—C62—H62B109.5
C30—C29—H29A121.4H62A—C62—H62B109.5
C29—C30—N2129.49 (15)C48—C62—H62C109.5
C29—C30—C25121.62 (15)H62A—C62—H62C109.5
N2—C30—C25108.85 (14)H62B—C62—H62C109.5
C12—N1—C1—C2179.43 (16)C43—N3—C32—C33178.35 (16)
C13—N1—C1—C23.4 (3)C44—N3—C32—C331.7 (3)
C12—N1—C1—C60.39 (17)C43—N3—C32—C370.38 (17)
C13—N1—C1—C6177.55 (14)C44—N3—C32—C37176.22 (14)
N1—C1—C2—C3177.99 (15)N3—C32—C33—C34179.80 (16)
C6—C1—C2—C31.0 (2)C37—C32—C33—C342.1 (2)
C1—C2—C3—C40.9 (2)C32—C33—C34—C351.1 (3)
C2—C3—C4—C50.4 (3)C33—C34—C35—C360.5 (3)
C3—C4—C5—C60.1 (2)C34—C35—C36—C371.1 (3)
C4—C5—C6—C10.1 (2)C35—C36—C37—C320.2 (2)
C4—C5—C6—C7179.48 (17)C35—C36—C37—C38179.64 (17)
C2—C1—C6—C50.5 (2)C33—C32—C37—C361.4 (2)
N1—C1—C6—C5178.65 (13)N3—C32—C37—C36179.59 (14)
C2—C1—C6—C7179.86 (14)C33—C32—C37—C38178.14 (14)
N1—C1—C6—C71.00 (17)N3—C32—C37—C380.03 (17)
C5—C6—C7—C83.6 (3)C36—C37—C38—C391.5 (3)
C1—C6—C7—C8176.83 (17)C32—C37—C38—C39179.01 (18)
C5—C6—C7—C12178.35 (17)C36—C37—C38—C43179.89 (17)
C1—C6—C7—C121.23 (17)C32—C37—C38—C430.42 (17)
C12—C7—C8—C90.3 (2)C43—C38—C39—C401.8 (2)
C6—C7—C8—C9177.59 (17)C37—C38—C39—C40176.64 (17)
C7—C8—C9—C101.6 (3)C38—C39—C40—C410.0 (3)
C8—C9—C10—C111.8 (3)C39—C40—C41—C421.4 (3)
C9—C10—C11—C120.6 (3)C40—C41—C42—C430.9 (2)
C10—C11—C12—N1177.13 (16)C41—C42—C43—N3177.46 (15)
C10—C11—C12—C70.7 (2)C41—C42—C43—C381.0 (2)
C1—N1—C12—C11178.50 (16)C32—N3—C43—C42176.13 (16)
C13—N1—C12—C111.3 (3)C44—N3—C43—C427.3 (3)
C1—N1—C12—C70.41 (17)C32—N3—C43—C380.65 (17)
C13—N1—C12—C7176.81 (14)C44—N3—C43—C38175.96 (14)
C8—C7—C12—C110.9 (2)C39—C38—C43—C422.4 (2)
C6—C7—C12—C11179.28 (15)C37—C38—C43—C42176.44 (14)
C8—C7—C12—N1177.37 (14)C39—C38—C43—N3179.48 (14)
C6—C7—C12—N11.02 (17)C37—C38—C43—N30.65 (17)
C12—N1—C13—C1458.8 (2)C43—N3—C44—C49134.06 (16)
C1—N1—C13—C14124.46 (17)C32—N3—C44—C4949.9 (2)
C12—N1—C13—C18119.32 (17)C43—N3—C44—C4546.4 (2)
C1—N1—C13—C1857.4 (2)C32—N3—C44—C45129.62 (16)
C18—C13—C14—C150.9 (3)C49—C44—C45—C460.2 (2)
N1—C13—C14—C15179.08 (15)N3—C44—C45—C46179.35 (14)
C13—C14—C15—C160.7 (3)C44—C45—C46—C471.5 (2)
C13—C14—C15—C31177.85 (17)C44—C45—C46—N4179.82 (14)
C14—C15—C16—C170.1 (3)C61—N4—C46—C45118.59 (17)
C31—C15—C16—C17178.67 (17)C50—N4—C46—C4567.0 (2)
C15—C16—C17—C180.7 (2)C61—N4—C46—C4762.7 (2)
C15—C16—C17—N2178.26 (15)C50—N4—C46—C47111.75 (18)
C19—N2—C17—C18123.85 (17)C45—C46—C47—C481.2 (2)
C30—N2—C17—C1856.5 (2)N4—C46—C47—C48179.92 (14)
C19—N2—C17—C1655.1 (2)C46—C47—C48—C490.7 (2)
C30—N2—C17—C16124.50 (17)C46—C47—C48—C62179.13 (16)
C16—C17—C18—C130.5 (2)C45—C44—C49—C482.1 (2)
N2—C17—C18—C13178.47 (14)N3—C44—C49—C48177.40 (14)
C14—C13—C18—C170.3 (2)C47—C48—C49—C442.4 (2)
N1—C13—C18—C17178.44 (14)C62—C48—C49—C44177.48 (15)
C30—N2—C19—C20178.56 (16)C61—N4—C50—C51178.61 (16)
C17—N2—C19—C201.8 (3)C46—N4—C50—C516.2 (3)
C30—N2—C19—C240.78 (17)C61—N4—C50—C551.23 (17)
C17—N2—C19—C24178.90 (14)C46—N4—C50—C55173.99 (14)
N2—C19—C20—C21179.87 (16)N4—C50—C51—C52179.64 (16)
C24—C19—C20—C210.6 (2)C55—C50—C51—C520.2 (2)
C19—C20—C21—C220.6 (3)C50—C51—C52—C530.9 (3)
C20—C21—C22—C230.9 (3)C51—C52—C53—C541.0 (3)
C21—C22—C23—C240.1 (3)C52—C53—C54—C550.4 (3)
C22—C23—C24—C191.3 (2)C53—C54—C55—C500.2 (2)
C22—C23—C24—C25179.13 (17)C53—C54—C55—C56178.33 (17)
C20—C19—C24—C231.6 (2)C51—C50—C55—C540.4 (2)
N2—C19—C24—C23179.01 (14)N4—C50—C55—C54179.78 (14)
C20—C19—C24—C25178.74 (14)C51—C50—C55—C56178.56 (15)
N2—C19—C24—C250.66 (17)N4—C50—C55—C561.29 (17)
C23—C24—C25—C260.9 (3)C54—C55—C56—C571.5 (3)
C19—C24—C25—C26178.68 (17)C50—C55—C56—C57177.22 (17)
C23—C24—C25—C30179.31 (17)C54—C55—C56—C61179.58 (17)
C19—C24—C25—C300.30 (17)C50—C55—C56—C610.88 (17)
C30—C25—C26—C270.2 (2)C61—C56—C57—C580.1 (2)
C24—C25—C26—C27178.01 (17)C55—C56—C57—C58178.03 (16)
C25—C26—C27—C280.1 (3)C56—C57—C58—C590.5 (2)
C26—C27—C28—C290.2 (3)C57—C58—C59—C600.7 (3)
C27—C28—C29—C300.5 (3)C58—C59—C60—C610.5 (2)
C28—C29—C30—N2178.15 (17)C59—C60—C61—N4177.70 (15)
C28—C29—C30—C250.7 (3)C59—C60—C61—C560.1 (2)
C19—N2—C30—C29178.33 (17)C50—N4—C61—C60177.37 (16)
C17—N2—C30—C291.4 (3)C46—N4—C61—C607.4 (3)
C19—N2—C30—C250.59 (17)C50—N4—C61—C560.66 (17)
C17—N2—C30—C25179.09 (14)C46—N4—C61—C56174.60 (14)
C26—C25—C30—C290.5 (2)C57—C56—C61—C600.1 (2)
C24—C25—C30—C29178.12 (15)C55—C56—C61—C60178.35 (14)
C26—C25—C30—N2178.48 (14)C57—C56—C61—N4178.29 (14)
C24—C25—C30—N20.18 (17)C55—C56—C61—N40.14 (17)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg3—Cg6 and Cg9 are the centroids of the C44–C49, C7–C12, C56–C61, C1–C6, C19–C24 and C32–C37 benzene rings while Cg2, Cg7 and Cg8 are the centroids of the N4/C50/C55/C56/C61, N2/C19/C24/C25/C30 and N3/C32/C37/C38/C43 pyrrole rings.
D—H···AD—HH···AD···AD—H···A
C9—H9A···Cg1i0.952.963.776 (2)145
C5—H5A···Cg2ii0.952.773.6969 (19)165
C53—H53A···Cg3iii0.952.763.5983 (19)148
C8—H8A···Cg4ii0.952.813.7122 (19)160
C49—H49A···Cg50.952.983.8654 (16)156
C57—H57A···Cg6iv0.952.853.3776 (17)117
C58—H58A···Cg7iv0.952.883.3749 (18)114
C59—H59A···Cg8v0.952.663.5084 (18)149
C60—H60A···Cg9v0.952.743.5180 (17)140
Symmetry codes: (i) x1/2, y+3/2, z+1/2; (ii) x+1/2, y+3/2, z+1/2; (iii) x, y, z1; (iv) x, y+1, z+1; (v) x1, y, z.

Experimental details

Crystal data
Chemical formulaC31H22N2
Mr422.51
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)9.2503 (1), 29.3854 (4), 16.2616 (2)
β (°) 96.901 (1)
V3)4388.27 (9)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.26 × 0.23 × 0.22
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.981, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
42985, 10834, 7284
Rint0.041
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.117, 1.03
No. of reflections10834
No. of parameters598
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.22

Computer programs: APEX2 (Bruker, 2006), SAINT-Plus (Bruker, 2006), SHELXTL (Sheldrick, 2008).

Table 1. C—H···π-electron ring interactions. The centroids Cg1, Cg2, Cg3, Cg4, Cg5, Cg6, Cg7, Cg8 and Cg9 are the centroids of the respective rings C44–C49, N4/C50/C55/C56/C61, C7—C12, C56—C61, C1—C6, C19—C24, N2/C19/C24/C25/C30, N3/C32/C37/C38/C43 and C32—C37. The centroids Cg1, Cg3—Cg6 and Cg9 are pertinent to the benzene rings while the centroids Cg2, Cg7 and Cg8 are pertinent to the pyrrole rings. top
C—H···CgD-HH···CgD···CgD-H···Cg
C9-H9A··· Cg1i0.952.9593.776 (2)145
C5-H5A··· Cg2ii0.952.7703.6969 (19)165
C53-H53A··· Cg3iii0.952.7553.5983 (19)148
C8-H8A··· Cg4ii0.952.8053.7122 (19)160
C49-H49A··· Cg50.952.9773.8654 (16)156
C57-H57A··· Cg6iv0.952.8453.3776 (17)117
C58-H58A··· Cg7iv0.952.8783.3749 (18)114
C59-H59A··· Cg8v0.952.6583.5084 (18)149
C60-H60A··· Cg9v0.952.7383.5180 (17)140
Symmetry codes: (i) x - 1/2, -y + 3/2, z + 1/2; (ii) x + 1/2, -y + 3/2, z + 1/2; (iii) x, y, z - 1; (iv) -x, -y + 1, -z + 1; (v) x - 1, y, z.
Table 2. Distances (Å) between the centroids of the rings involved in the π-electron ring···π-electron ring interactions which are present in the title structure. The centroids Cg10, Cg11 and Cg12 are pertinent to the benzene, pyrrole and benzene rings, respectively. top
Cgi···Cgjdistance (Å)1-st ring2-nd ring
Cg10···Cg10vi3.7698 (10)C38//C39···C43C38//C39···C43
Cg11···Cg11vii3.8292 (9)N2//C19···C30N2//C19···C30
Cg12···Cg11vi3.9429 (10)C25//C26···C30N2//C19···C30
Cg11···Cg12vi3.9431 (10)N2//C19···C30C25//C26···C30
Symmetry codes: (vi) -x + 1, -y + 1, -z + 1; (vii) x + 3/2, -y + 3/2, z + 5/2.
 

Acknowledgements

This paper was supported by the Konyang University Research Fund in 2012 and also the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2011–0007756). The authors gratefully acknowledge the use of the SC-XRD in the Korea Basic Science Institute (Jeonju Center).

References

First citationBruker (2006). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationKwon, T.-H., Kim, M. K., Kwon, J., Shin, D.-Y., Park, S. J., Lee, C.-L., Kim, J.-J. & Hong, J.-I. (2007). Chem. Mater. 19, 3673–3680.  Web of Science CrossRef CAS
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSun, Y.-H., Zhu, X.-H., Chen, Z., Zhang, Y. & Cao, Y. (2006). J. Org. Chem. 71, 6281–6284.  Web of Science CSD CrossRef PubMed CAS

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