


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810018660/om2337sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810018660/om2337Isup2.hkl |
CCDC reference: 745064
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.062
- wR factor = 0.148
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 61 PLAT481_ALERT_4_C Long D...A H-Bond Reported C10 .. CG2 .. 4.05 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C21 H18 N2
Alert level G PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c ....... P21/n
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was synthesized via the imine reaction between aniline and 9-ethyl-9H-carbazol-3-carbaldehyde in ethanol. In a round bottom flask fitted with a magnetic stirrer a solution was prepared from 9-ethyl-9H-carbazol-3-carbaldehyde (1.116 g, 5 mmol) and aniline (0.70 g, 7.5 mmol) in 50 ml ethanol at ambient temperature. After stirring for 2 h, the solution was left for crystallization overnight, after which time the product was precipitated as yellow crystals. The crude product was separated by filtration and washed with ethanol. Yellow, transparent crystals suitable for the X-ray diffraction analysis were grown from tetrahydrofuran by slow evaporation technique at ambient temperature, mp. 407 K. FT—IR (KBr) νmax (cm-1): 3048 (Ar—H), 2973 (-CH3), 2930 (-CH2-), 1618 (C=N), 1587, 1567 (Ar—N), 1489, 1473, 1461 (Ar C=C); 1HNMR (300 MHz, CDCl3, ppm): 1.46 (t, J = 7.3 Hz, 3H, CH3), 4.38 (q, J = 7.3 Hz, 2H, -CH2-), 7.21-7.59 (m, 9H, ArH), 8.07 (dd, J = 8.5 and 1.8 Hz, 1H, H2), 8.18 (dt, J = 7.9 and 0.8 Hz, 1H, H5), 8.64 (s, 1H, H12), 8.65 (d, J= 1.8, 1H, H4). UV-Vis, [EtOH, λmax (nm), (ε)] = 238 (25800), 293 (22100), 338 (18500).
All non-hydrogen atoms were refined anisotropically; the hydrogen atoms were positioned geometrically and allowed to ride on their corresponding parent atoms with C—H distances of 0.93Å (aromatic), 0.96Å (methyl), and 0.97Å (methylene) with Uiso(H) =1.5Ueq(C) of the parent atom for the methyl group and 1.2Ueq(C) for the rest.
The structure of the title compound is depicted in (Fig. 1). The bond lengths and internal bond angles of the carbazole skeleton are comparable to those of related molecules (Wang et al., 2008; Huang et al., 2008). The carbazole and phenyl skeletons are essentially planar with r.m.s deviations of 0.021Å (carbazole ring) and 0.008Å (phenyl ring). The phenyl ring is twisted away from the carbazole ring by 67.45 (05)°. The ethyl group protrudes out of the plane of the carbazole skeleton as indicated by the C9A—N9—C10—C11 torsion angle of 86.0 (3)°. The only force that stack the molecules appears to be π-ring C—H···Cg intermolecular interactions among the benzene rings of carbazole and the hydrogen atoms H5, H10A and H12 (Fig. 2).
For background to photoconductive properties see: Segura (1998); Grigoras & Antonoaia (2005). For geometrical parameters in related structures, see: Wang et al. (2008); Huang et al. (2008).
Data collection: CrystalStructure (Rigaku & Rigaku/MSC, 2003); cell refinement: CrystalStructure (Rigaku & Rigaku/MSC, 2003); data reduction: SORTAV (Blessing, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C21H18N2 | F(000) = 632 |
Mr = 298.37 | Dx = 1.234 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8828 reflections |
a = 15.3350 (3) Å | θ = 2.3–25.3° |
b = 5.9692 (10) Å | µ = 0.07 mm−1 |
c = 17.5447 (3) Å | T = 295 K |
β = 91.162 (1)° | Prism, yellow |
V = 1605.7 (3) Å3 | 0.6 × 0.4 × 0.2 mm |
Z = 4 |
Rigaku R-AXIS RAPID S diffractometer | Rint = 0.030 |
Graphite monochromator | θmax = 25.2°, θmin = 2.3° |
ω scans | h = −18→18 |
28963 measured reflections | k = −6→7 |
2838 independent reflections | l = −20→20 |
2821 reflections with I > 2σ(I) |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.148 | w = 1/[σ2(Fo2) + (0.0417P)2 + 0.4831P] where P = (Fo2 + 2Fc2)/3 |
S = 1.41 | (Δ/σ)max = 0.002 |
2838 reflections | Δρmax = 0.14 e Å−3 |
209 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008) |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0123 (17) |
C21H18N2 | V = 1605.7 (3) Å3 |
Mr = 298.37 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.3350 (3) Å | µ = 0.07 mm−1 |
b = 5.9692 (10) Å | T = 295 K |
c = 17.5447 (3) Å | 0.6 × 0.4 × 0.2 mm |
β = 91.162 (1)° |
Rigaku R-AXIS RAPID S diffractometer | 2821 reflections with I > 2σ(I) |
28963 measured reflections | Rint = 0.030 |
2838 independent reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.41 | Δρmax = 0.14 e Å−3 |
2838 reflections | Δρmin = −0.13 e Å−3 |
209 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.53644 (12) | −0.2326 (3) | 0.39241 (11) | 0.0627 (5) | |
N9 | 0.15252 (12) | 0.1918 (3) | 0.39179 (10) | 0.0567 (5) | |
C1 | 0.31091 (15) | 0.1662 (4) | 0.42835 (13) | 0.0583 (6) | |
H1 | 0.3127 | 0.2991 | 0.456 | 0.07* | |
C2 | 0.38396 (14) | 0.0359 (4) | 0.42111 (12) | 0.0580 (6) | |
H2 | 0.436 | 0.0829 | 0.444 | 0.07* | |
C3 | 0.38256 (14) | −0.1669 (4) | 0.38000 (12) | 0.0530 (5) | |
C4 | 0.30554 (14) | −0.2380 (4) | 0.34500 (12) | 0.0531 (5) | |
H4 | 0.304 | −0.3717 | 0.3178 | 0.064* | |
C4A | 0.23047 (13) | −0.1080 (4) | 0.35070 (11) | 0.0511 (5) | |
C4B | 0.14167 (13) | −0.1318 (4) | 0.32328 (11) | 0.0520 (5) | |
C5 | 0.09773 (15) | −0.2925 (4) | 0.27965 (12) | 0.0611 (6) | |
H5 | 0.1274 | −0.4154 | 0.2605 | 0.073* | |
C6 | 0.00979 (16) | −0.2669 (5) | 0.26525 (14) | 0.0678 (7) | |
H6 | −0.0202 | −0.3737 | 0.2364 | 0.081* | |
C7 | −0.03468 (16) | −0.0827 (5) | 0.29346 (14) | 0.0684 (7) | |
H7 | −0.0942 | −0.0697 | 0.2833 | 0.082* | |
C8 | 0.00672 (15) | 0.0809 (4) | 0.33593 (13) | 0.0636 (6) | |
H8 | −0.0235 | 0.2044 | 0.354 | 0.076* | |
C8A | 0.09549 (14) | 0.0541 (4) | 0.35072 (11) | 0.0542 (5) | |
C9A | 0.23398 (14) | 0.0931 (4) | 0.39289 (11) | 0.0522 (5) | |
C10 | 0.12624 (16) | 0.3717 (4) | 0.44220 (14) | 0.0651 (6) | |
H10A | 0.0808 | 0.4594 | 0.4171 | 0.078* | |
H10B | 0.1757 | 0.4697 | 0.452 | 0.078* | |
C11 | 0.0931 (2) | 0.2849 (5) | 0.51707 (15) | 0.0874 (9) | |
H11A | 0.0766 | 0.4088 | 0.5486 | 0.131* | |
H11B | 0.1382 | 0.2003 | 0.5425 | 0.131* | |
H11C | 0.0434 | 0.1904 | 0.5077 | 0.131* | |
C12 | 0.46110 (14) | −0.3017 (4) | 0.37283 (12) | 0.0553 (5) | |
H12 | 0.4557 | −0.4456 | 0.3529 | 0.066* | |
C13 | 0.60811 (14) | −0.3801 (4) | 0.38491 (12) | 0.0550 (5) | |
C14 | 0.61128 (15) | −0.5881 (4) | 0.41922 (13) | 0.0636 (6) | |
H14 | 0.5646 | −0.6363 | 0.448 | 0.076* | |
C15 | 0.68271 (18) | −0.7249 (5) | 0.41133 (16) | 0.0767 (7) | |
H15 | 0.6844 | −0.8639 | 0.4352 | 0.092* | |
C16 | 0.75146 (18) | −0.6566 (5) | 0.36830 (18) | 0.0818 (8) | |
H16 | 0.7992 | −0.7505 | 0.362 | 0.098* | |
C17 | 0.74958 (16) | −0.4498 (5) | 0.33467 (16) | 0.0795 (8) | |
H17 | 0.7964 | −0.4032 | 0.3057 | 0.095* | |
C18 | 0.67877 (15) | −0.3096 (4) | 0.34333 (14) | 0.0674 (6) | |
H18 | 0.6786 | −0.1679 | 0.3212 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0557 (11) | 0.0652 (12) | 0.0671 (12) | 0.0002 (9) | −0.0018 (9) | −0.0068 (10) |
N9 | 0.0579 (11) | 0.0550 (11) | 0.0573 (10) | 0.0052 (9) | 0.0051 (8) | −0.0043 (9) |
C1 | 0.0646 (13) | 0.0538 (13) | 0.0566 (12) | −0.0033 (11) | 0.0010 (10) | −0.0071 (10) |
C2 | 0.0570 (12) | 0.0616 (14) | 0.0553 (12) | −0.0056 (11) | −0.0028 (10) | −0.0016 (11) |
C3 | 0.0549 (12) | 0.0564 (13) | 0.0477 (11) | 0.0000 (10) | 0.0020 (9) | 0.0005 (10) |
C4 | 0.0592 (12) | 0.0516 (12) | 0.0485 (11) | −0.0004 (10) | 0.0014 (9) | −0.0044 (9) |
C4A | 0.0549 (12) | 0.0514 (12) | 0.0470 (11) | −0.0026 (10) | 0.0012 (9) | 0.0000 (9) |
C4B | 0.0558 (12) | 0.0567 (12) | 0.0435 (10) | −0.0015 (10) | 0.0022 (9) | 0.0047 (9) |
C5 | 0.0686 (14) | 0.0626 (14) | 0.0519 (12) | −0.0042 (11) | −0.0041 (10) | −0.0013 (11) |
C6 | 0.0647 (14) | 0.0795 (17) | 0.0589 (13) | −0.0129 (13) | −0.0095 (11) | 0.0054 (12) |
C7 | 0.0551 (13) | 0.0889 (19) | 0.0611 (14) | −0.0045 (13) | −0.0032 (11) | 0.0162 (13) |
C8 | 0.0590 (13) | 0.0738 (16) | 0.0582 (13) | 0.0065 (12) | 0.0053 (10) | 0.0093 (12) |
C8A | 0.0573 (12) | 0.0593 (13) | 0.0461 (11) | −0.0012 (10) | 0.0037 (9) | 0.0062 (10) |
C9A | 0.0569 (12) | 0.0518 (12) | 0.0480 (11) | 0.0003 (10) | 0.0051 (9) | 0.0009 (9) |
C10 | 0.0702 (15) | 0.0567 (13) | 0.0688 (15) | 0.0077 (12) | 0.0092 (12) | −0.0066 (11) |
C11 | 0.101 (2) | 0.102 (2) | 0.0603 (15) | 0.0029 (18) | 0.0132 (14) | −0.0073 (15) |
C12 | 0.0577 (13) | 0.0579 (13) | 0.0505 (12) | −0.0021 (10) | 0.0031 (9) | −0.0029 (10) |
C13 | 0.0519 (12) | 0.0608 (13) | 0.0524 (12) | −0.0049 (10) | −0.0024 (9) | −0.0068 (10) |
C14 | 0.0626 (14) | 0.0665 (15) | 0.0619 (14) | −0.0044 (12) | 0.0076 (11) | −0.0003 (11) |
C15 | 0.0802 (17) | 0.0668 (16) | 0.0833 (18) | 0.0074 (14) | 0.0044 (14) | 0.0030 (14) |
C16 | 0.0649 (16) | 0.082 (2) | 0.099 (2) | 0.0120 (14) | 0.0043 (14) | −0.0125 (17) |
C17 | 0.0560 (14) | 0.093 (2) | 0.0902 (19) | −0.0115 (14) | 0.0155 (13) | −0.0126 (16) |
C18 | 0.0640 (14) | 0.0665 (15) | 0.0720 (15) | −0.0111 (12) | 0.0052 (12) | −0.0017 (12) |
N1—C12 | 1.268 (3) | C7—C8 | 1.376 (3) |
N1—C13 | 1.416 (3) | C7—H7 | 0.93 |
N9—C9A | 1.381 (3) | C8—C8A | 1.390 (3) |
N9—C8A | 1.391 (3) | C8—H8 | 0.93 |
N9—C10 | 1.453 (3) | C10—C11 | 1.510 (3) |
C1—C2 | 1.372 (3) | C10—H10A | 0.97 |
C1—C9A | 1.393 (3) | C10—H10B | 0.97 |
C1—H1 | 0.93 | C11—H11A | 0.96 |
C2—C3 | 1.409 (3) | C11—H11B | 0.96 |
C2—H2 | 0.93 | C11—H11C | 0.96 |
C3—C4 | 1.386 (3) | C12—H12 | 0.93 |
C3—C12 | 1.456 (3) | C13—C14 | 1.380 (3) |
C4—C4A | 1.393 (3) | C13—C18 | 1.384 (3) |
C4—H4 | 0.93 | C14—C15 | 1.375 (3) |
C4A—C9A | 1.411 (3) | C14—H14 | 0.93 |
C4A—C4B | 1.442 (3) | C15—C16 | 1.371 (4) |
C4B—C5 | 1.393 (3) | C15—H15 | 0.93 |
C4B—C8A | 1.407 (3) | C16—C17 | 1.368 (4) |
C5—C6 | 1.376 (3) | C16—H16 | 0.93 |
C5—H5 | 0.93 | C17—C18 | 1.382 (4) |
C6—C7 | 1.390 (4) | C17—H17 | 0.93 |
C6—H6 | 0.93 | C18—H18 | 0.93 |
C12—N1—C13 | 118.5 (2) | N9—C9A—C1 | 129.1 (2) |
C9A—N9—C8A | 108.32 (18) | N9—C9A—C4A | 109.32 (18) |
C9A—N9—C10 | 124.65 (19) | C1—C9A—C4A | 121.6 (2) |
C8A—N9—C10 | 124.95 (19) | N9—C10—C11 | 112.2 (2) |
C2—C1—C9A | 117.8 (2) | N9—C10—H10A | 109.2 |
C2—C1—H1 | 121.1 | C11—C10—H10A | 109.2 |
C9A—C1—H1 | 121.1 | N9—C10—H10B | 109.2 |
C1—C2—C3 | 122.0 (2) | C11—C10—H10B | 109.2 |
C1—C2—H2 | 119 | H10A—C10—H10B | 107.9 |
C3—C2—H2 | 119 | C10—C11—H11A | 109.5 |
C4—C3—C2 | 119.6 (2) | C10—C11—H11B | 109.5 |
C4—C3—C12 | 119.4 (2) | H11A—C11—H11B | 109.5 |
C2—C3—C12 | 121.0 (2) | C10—C11—H11C | 109.5 |
C3—C4—C4A | 119.7 (2) | H11A—C11—H11C | 109.5 |
C3—C4—H4 | 120.1 | H11B—C11—H11C | 109.5 |
C4A—C4—H4 | 120.1 | N1—C12—C3 | 123.2 (2) |
C4—C4A—C9A | 119.24 (19) | N1—C12—H12 | 118.4 |
C4—C4A—C4B | 134.2 (2) | C3—C12—H12 | 118.4 |
C9A—C4A—C4B | 106.53 (18) | C14—C13—C18 | 118.8 (2) |
C5—C4B—C8A | 119.4 (2) | C14—C13—N1 | 122.6 (2) |
C5—C4B—C4A | 134.0 (2) | C18—C13—N1 | 118.5 (2) |
C8A—C4B—C4A | 106.66 (19) | C15—C14—C13 | 120.7 (2) |
C6—C5—C4B | 119.1 (2) | C15—C14—H14 | 119.6 |
C6—C5—H5 | 120.5 | C13—C14—H14 | 119.6 |
C4B—C5—H5 | 120.5 | C16—C15—C14 | 120.1 (3) |
C5—C6—C7 | 120.6 (2) | C16—C15—H15 | 119.9 |
C5—C6—H6 | 119.7 | C14—C15—H15 | 119.9 |
C7—C6—H6 | 119.7 | C17—C16—C15 | 119.7 (3) |
C8—C7—C6 | 122.0 (2) | C17—C16—H16 | 120.1 |
C8—C7—H7 | 119 | C15—C16—H16 | 120.1 |
C6—C7—H7 | 119 | C16—C17—C18 | 120.6 (2) |
C7—C8—C8A | 117.3 (2) | C16—C17—H17 | 119.7 |
C7—C8—H8 | 121.3 | C18—C17—H17 | 119.7 |
C8A—C8—H8 | 121.3 | C17—C18—C13 | 119.9 (2) |
N9—C8A—C8 | 129.2 (2) | C17—C18—H18 | 120 |
N9—C8A—C4B | 109.14 (18) | C13—C18—H18 | 120 |
C8—C8A—C4B | 121.7 (2) | ||
C9A—C1—C2—C3 | −0.6 (3) | C8A—N9—C9A—C1 | −178.4 (2) |
C1—C2—C3—C4 | 0.5 (3) | C10—N9—C9A—C1 | −14.2 (4) |
C1—C2—C3—C12 | 179.7 (2) | C8A—N9—C9A—C4A | 1.4 (2) |
C2—C3—C4—C4A | 0.1 (3) | C10—N9—C9A—C4A | 165.58 (19) |
C12—C3—C4—C4A | −179.05 (19) | C2—C1—C9A—N9 | 179.7 (2) |
C3—C4—C4A—C9A | −0.7 (3) | C2—C1—C9A—C4A | 0.0 (3) |
C3—C4—C4A—C4B | −178.9 (2) | C4—C4A—C9A—N9 | −179.11 (19) |
C4—C4A—C4B—C5 | −1.2 (4) | C4B—C4A—C9A—N9 | −0.5 (2) |
C9A—C4A—C4B—C5 | −179.6 (2) | C4—C4A—C9A—C1 | 0.7 (3) |
C4—C4A—C4B—C8A | 177.8 (2) | C4B—C4A—C9A—C1 | 179.34 (19) |
C9A—C4A—C4B—C8A | −0.6 (2) | C9A—N9—C10—C11 | −86.0 (3) |
C8A—C4B—C5—C6 | −0.8 (3) | C8A—N9—C10—C11 | 75.7 (3) |
C4A—C4B—C5—C6 | 178.0 (2) | C13—N1—C12—C3 | 178.29 (19) |
C4B—C5—C6—C7 | 0.3 (3) | C4—C3—C12—N1 | 168.4 (2) |
C5—C6—C7—C8 | 0.5 (4) | C2—C3—C12—N1 | −10.7 (3) |
C6—C7—C8—C8A | −0.8 (3) | C12—N1—C13—C14 | −56.6 (3) |
C9A—N9—C8A—C8 | 178.3 (2) | C12—N1—C13—C18 | 125.4 (2) |
C10—N9—C8A—C8 | 14.1 (4) | C18—C13—C14—C15 | −1.0 (3) |
C9A—N9—C8A—C4B | −1.7 (2) | N1—C13—C14—C15 | −179.1 (2) |
C10—N9—C8A—C4B | −165.92 (19) | C13—C14—C15—C16 | −0.8 (4) |
C7—C8—C8A—N9 | −179.8 (2) | C14—C15—C16—C17 | 1.5 (4) |
C7—C8—C8A—C4B | 0.3 (3) | C15—C16—C17—C18 | −0.4 (4) |
C5—C4B—C8A—N9 | −179.41 (18) | C16—C17—C18—C13 | −1.5 (4) |
C4A—C4B—C8A—N9 | 1.4 (2) | C14—C13—C18—C17 | 2.1 (3) |
C5—C4B—C8A—C8 | 0.5 (3) | N1—C13—C18—C17 | −179.7 (2) |
C4A—C4B—C8A—C8 | −178.60 (19) |
Cg1 and Cg2 are the centroids of the C1–C4/C4A/C9A and C4B/C5–C8/C8A rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cg1i | 0.93 | 2.87 | 3.587 (3) | 135 |
C12—H12···Cg2i | 0.93 | 2.98 | 3.660 (3) | 131 |
C10—H10A···Cg2ii | 0.97 | 3.25 | 4.050 (4) | 142 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C21H18N2 |
Mr | 298.37 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 15.3350 (3), 5.9692 (10), 17.5447 (3) |
β (°) | 91.162 (1) |
V (Å3) | 1605.7 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.6 × 0.4 × 0.2 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID S |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 28963, 2838, 2821 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.148, 1.41 |
No. of reflections | 2838 |
No. of parameters | 209 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.13 |
Computer programs: CrystalStructure (Rigaku & Rigaku/MSC, 2003), SORTAV (Blessing, 1995), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
C9A—N9—C10—C11 | −86.0 (3) | C2—C3—C12—N1 | −10.7 (3) |
C13—N1—C12—C3 | 178.29 (19) | C12—N1—C13—C14 | −56.6 (3) |
Cg1 and Cg2 are the centroids of the C1–C4/C4A/C9A and C4B/C5–C8/C8A rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cg1i | 0.93 | 2.87 | 3.587 (3) | 134.7 |
C12—H12···Cg2i | 0.93 | 2.98 | 3.660 (3) | 130.9 |
C10—H10A···Cg2ii | 0.97 | 3.25 | 4.050 (4) | 141.6 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x, y+1, z. |
The structure of the title compound is depicted in (Fig. 1). The bond lengths and internal bond angles of the carbazole skeleton are comparable to those of related molecules (Wang et al., 2008; Huang et al., 2008). The carbazole and phenyl skeletons are essentially planar with r.m.s deviations of 0.021Å (carbazole ring) and 0.008Å (phenyl ring). The phenyl ring is twisted away from the carbazole ring by 67.45 (05)°. The ethyl group protrudes out of the plane of the carbazole skeleton as indicated by the C9A—N9—C10—C11 torsion angle of 86.0 (3)°. The only force that stack the molecules appears to be π-ring C—H···Cg intermolecular interactions among the benzene rings of carbazole and the hydrogen atoms H5, H10A and H12 (Fig. 2).