Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045151/kp2134sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045151/kp2134Isup2.hkl |
CCDC reference: 667306
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.095
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22 PLAT480_ALERT_4_C Long H...A H-Bond Reported H10 .. O23 .. 2.69 Ang.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 10
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Compound I was synthesized according to the procedure described earlier (Prukała et al., 2007).
The hydrogen atoms were located in the difference Fourier maps and refined as 'riding model'. Isotropic displacement parameters for hydrogen atoms were set at 1.2 (1.3 for methyl group) times the Ueq values of appropriate carrier atoms. Weak restraints to the Uij components were appled due to the large values of Hirshfeld differences for some pairs of atoms.
Carbazole and its derivatives are very attractive compounds due to their electroactivity and luminescent properties (Hyun et al.., 2006). The aromatic rings in carbazole-containing compounds form relatively stable radical cations (holes) and many carbazole derivatives have sufficiently high triplet energy to host red, full-color triplet emitters (e.g. Anni et al., 2004). Such properties make them attractive components of light-emitting diodes, and photorefractive materials (Zhang et al., 2004). Very interesting are N-styryl-substituted carbazole derivatives with electron-withdrawing groups (Prukała et al., 2007). The title compound is a part of our studies on styryl-carbazole derivatives.
The molecule of the title compound (Fig. 1) is built of two approximately planar aromatic fragments, connected by the trans N—C=C—C moity (A). The maximum deviation from the mean plane of nine atoms of the carbazole moiety (B) is 0.0354 (16) Å and from the least-squares plane of the phenyl ring (C) - 0.0098 (12) Å. The overall conformation of the molecule (I) can be described by the dihedral angles between these three planar fragments: A/B: 34.26 (13)°, A/C: 11.19 (14)°, B/C: 45.34 (5)°. The molecule of (I) is significantly less twisted that the closely related methoxy-derivative (Prukała et al., 2007), in which the dihedral angle between the carbazole and phenyl planes is 64.29 (4)°. The bond lengths in the central N—C=C—C fragment show the lack of the delocalization (double C=C bond 1.296 (2) Å, single C—C: 1.480 (2) Å, N—C 1.404 (2) Å).
In the crystal structure centrosymmetric dimers generated by hydrogen bond C—H···O (C21—H···O23i , i = 1 - x, 1 - y, -1 - z) (Table 1, Fig. 2) are connected by C10···O23i (i = x, y, 1 + z) into the chains along the direction [001]. Additional C—H···π interaction (Cg3 in Table 1 denotes the middlepoint of the five-membered ring C5, C6, C11, N12) also support these chains.
The synthesis and catalytic activities of para-substituted (E)-N-styrylcarbazoles have recently been described by Prukała et al. (2007). For related literature, see Hyun et al. (2006); Anni et al. (2004); Zhang et al. (2004); Marciniec et al. (2005).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006).; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1989); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. The molecular structure of (I) with atom labels and the 50% probability displacement ellipsoids for non-H atoms. | |
Fig. 2. The chain along [001] formed by C—H···O interactions. |
C22H17NO | F(000) = 656 |
Mr = 311.37 | Dx = 1.239 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3826 reflections |
a = 8.6392 (6) Å | θ = 4–23° |
b = 24.6618 (17) Å | µ = 0.08 mm−1 |
c = 8.0637 (7) Å | T = 294 K |
β = 103.665 (7)° | Block, colourless |
V = 1669.4 (2) Å3 | 0.45 × 0.2 × 0.1 mm |
Z = 4 |
KUMA KM4CCD diffractometer | 1618 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 25.0°, θmin = 2.4° |
ω–scan | h = −10→10 |
10180 measured reflections | k = −29→28 |
2931 independent reflections | l = −5→9 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.040P)2] where P = (Fo2 + 2Fc2)/3 |
2931 reflections | (Δ/σ)max = 0.001 |
218 parameters | Δρmax = 0.17 e Å−3 |
10 restraints | Δρmin = −0.12 e Å−3 |
C22H17NO | V = 1669.4 (2) Å3 |
Mr = 311.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.6392 (6) Å | µ = 0.08 mm−1 |
b = 24.6618 (17) Å | T = 294 K |
c = 8.0637 (7) Å | 0.45 × 0.2 × 0.1 mm |
β = 103.665 (7)° |
KUMA KM4CCD diffractometer | 1618 reflections with I > 2σ(I) |
10180 measured reflections | Rint = 0.030 |
2931 independent reflections |
R[F2 > 2σ(F2)] = 0.042 | 10 restraints |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.17 e Å−3 |
2931 reflections | Δρmin = −0.12 e Å−3 |
218 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6313 (2) | 0.34028 (7) | 0.3173 (2) | 0.0695 (5) | |
H1 | 0.7133 | 0.3583 | 0.2679 | 0.083* | |
C2 | 0.6783 (3) | 0.31391 (8) | 0.4715 (2) | 0.0869 (6) | |
H2 | 0.7972 | 0.3141 | 0.5305 | 0.104* | |
C3 | 0.5693 (3) | 0.28726 (8) | 0.5428 (3) | 0.0976 (7) | |
H3 | 0.6060 | 0.2718 | 0.6455 | 0.117* | |
C4 | 0.4104 (3) | 0.28523 (7) | 0.4613 (3) | 0.0883 (6) | |
H4 | 0.3244 | 0.2687 | 0.4982 | 0.106* | |
C5 | 0.3595 (2) | 0.31135 (7) | 0.3037 (2) | 0.0658 (5) | |
C6 | 0.2073 (2) | 0.31597 (7) | 0.1820 (2) | 0.0660 (5) | |
C7 | 0.0531 (3) | 0.29664 (8) | 0.1758 (3) | 0.0868 (6) | |
H7 | 0.0483 | 0.2763 | 0.2709 | 0.104* | |
C8 | −0.0687 (3) | 0.31089 (10) | 0.0405 (4) | 0.0981 (7) | |
H8 | −0.1770 | 0.2955 | 0.0323 | 0.118* | |
C9 | −0.0414 (2) | 0.34367 (9) | −0.0883 (3) | 0.0935 (6) | |
H9 | −0.1301 | 0.3553 | −0.1824 | 0.112* | |
C10 | 0.1086 (2) | 0.36252 (8) | −0.0885 (2) | 0.0783 (5) | |
H10 | 0.1317 | 0.3867 | −0.1733 | 0.094* | |
C11 | 0.2321 (2) | 0.34749 (7) | 0.0473 (2) | 0.0623 (5) | |
N12 | 0.39291 (17) | 0.36185 (6) | 0.07909 (16) | 0.0623 (4) | |
C13 | 0.4717 (2) | 0.33970 (6) | 0.2363 (2) | 0.0587 (4) | |
C14 | 0.4584 (2) | 0.39064 (7) | −0.0382 (2) | 0.0695 (5) | |
H14 | 0.4206 | 0.3852 | −0.1545 | 0.083* | |
C15 | 0.5778 (2) | 0.42392 (7) | −0.0040 (2) | 0.0697 (5) | |
H15 | 0.6239 | 0.4337 | 0.1187 | 0.084* | |
C16 | 0.6464 (2) | 0.45242 (7) | −0.1315 (2) | 0.0617 (4) | |
C17 | 0.60586 (19) | 0.43922 (7) | −0.3039 (2) | 0.0657 (5) | |
H17 | 0.5348 | 0.4145 | −0.3568 | 0.079* | |
C18 | 0.67108 (19) | 0.46792 (7) | −0.4199 (2) | 0.0652 (5) | |
H18 | 0.6385 | 0.4598 | −0.5410 | 0.078* | |
C19 | 0.77922 (19) | 0.50939 (6) | −0.36486 (19) | 0.0565 (4) | |
C20 | 0.8206 (2) | 0.52105 (7) | −0.1916 (2) | 0.0675 (5) | |
H20 | 0.9034 | 0.5502 | −0.1474 | 0.081* | |
C21 | 0.7553 (2) | 0.49312 (8) | −0.0779 (2) | 0.0711 (5) | |
H21 | 0.7872 | 0.5024 | 0.0456 | 0.085* | |
C22 | 0.8457 (2) | 0.53991 (7) | −0.4901 (2) | 0.0637 (5) | |
O23 | 0.80691 (16) | 0.52895 (6) | −0.64132 (16) | 0.0937 (4) | |
C24 | 0.9629 (2) | 0.58373 (8) | −0.4314 (2) | 0.0944 (6) | |
H24A | 1.0224 | 0.5948 | −0.5177 | 0.123* | |
H24B | 1.0298 | 0.5776 | −0.3271 | 0.123* | |
H24C | 0.9131 | 0.6124 | −0.4135 | 0.123* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0778 (10) | 0.0578 (11) | 0.0715 (12) | 0.0015 (10) | 0.0151 (9) | 0.0018 (10) |
C2 | 0.1083 (16) | 0.0629 (13) | 0.0807 (14) | 0.0066 (11) | 0.0050 (11) | 0.0055 (11) |
C3 | 0.145 (2) | 0.0728 (15) | 0.0719 (13) | 0.0074 (14) | 0.0188 (14) | 0.0206 (11) |
C4 | 0.1262 (19) | 0.0629 (13) | 0.0841 (12) | −0.0049 (13) | 0.0416 (14) | 0.0146 (10) |
C5 | 0.0882 (11) | 0.0450 (10) | 0.0725 (10) | 0.0003 (10) | 0.0353 (8) | −0.0001 (8) |
C6 | 0.0784 (10) | 0.0485 (10) | 0.0816 (12) | −0.0028 (9) | 0.0398 (8) | −0.0085 (10) |
C7 | 0.0925 (14) | 0.0673 (14) | 0.1162 (16) | −0.0165 (12) | 0.0555 (14) | −0.0180 (12) |
C8 | 0.0730 (16) | 0.0923 (17) | 0.1363 (19) | −0.0190 (13) | 0.0395 (15) | −0.0400 (16) |
C9 | 0.0707 (12) | 0.0970 (17) | 0.1110 (16) | −0.0033 (11) | 0.0181 (13) | −0.0277 (14) |
C10 | 0.0752 (12) | 0.0790 (14) | 0.0813 (12) | −0.0003 (10) | 0.0194 (11) | −0.0064 (11) |
C11 | 0.0657 (13) | 0.0575 (12) | 0.0683 (12) | 0.0008 (10) | 0.0250 (10) | −0.0062 (9) |
N12 | 0.0648 (10) | 0.0642 (9) | 0.0617 (9) | −0.0014 (8) | 0.0228 (7) | 0.0074 (7) |
C13 | 0.0709 (9) | 0.0476 (10) | 0.0620 (11) | 0.0008 (9) | 0.0248 (9) | −0.0012 (9) |
C14 | 0.0724 (12) | 0.0704 (13) | 0.0715 (12) | −0.0007 (10) | 0.0288 (9) | 0.0094 (9) |
C15 | 0.0770 (13) | 0.0717 (13) | 0.0636 (11) | −0.0008 (11) | 0.0226 (9) | 0.0047 (9) |
C16 | 0.0659 (11) | 0.0625 (12) | 0.0614 (9) | 0.0104 (10) | 0.0243 (8) | 0.0057 (8) |
C17 | 0.0626 (11) | 0.0638 (12) | 0.0714 (9) | −0.0094 (9) | 0.0174 (8) | −0.0048 (8) |
C18 | 0.0656 (11) | 0.0712 (12) | 0.0610 (10) | −0.0011 (8) | 0.0197 (8) | −0.0023 (8) |
C19 | 0.0590 (10) | 0.0553 (10) | 0.0595 (8) | 0.0071 (7) | 0.0228 (7) | 0.0021 (7) |
C20 | 0.0764 (12) | 0.0665 (12) | 0.0635 (9) | −0.0068 (10) | 0.0240 (9) | −0.0034 (9) |
C21 | 0.0856 (13) | 0.0710 (13) | 0.0601 (10) | −0.0057 (11) | 0.0239 (10) | −0.0033 (10) |
C22 | 0.0652 (11) | 0.0652 (12) | 0.0663 (12) | 0.0037 (10) | 0.0269 (9) | 0.0039 (9) |
O23 | 0.0997 (10) | 0.1208 (12) | 0.0646 (8) | −0.0205 (9) | 0.0272 (7) | 0.0072 (8) |
C24 | 0.1189 (17) | 0.0773 (14) | 0.0996 (15) | −0.0230 (13) | 0.0509 (13) | −0.0082 (12) |
C1—C2 | 1.377 (2) | N12—C13 | 1.4003 (19) |
C1—C13 | 1.379 (2) | N12—C14 | 1.404 (2) |
C1—H1 | 0.9960 | C14—C15 | 1.296 (2) |
C2—C3 | 1.380 (3) | C14—H14 | 0.9270 |
C2—H2 | 1.0250 | C15—C16 | 1.480 (2) |
C3—C4 | 1.375 (3) | C15—H15 | 1.0050 |
C3—H3 | 0.8988 | C16—C21 | 1.374 (2) |
C4—C5 | 1.400 (2) | C16—C17 | 1.389 (2) |
C4—H4 | 0.9550 | C17—C18 | 1.394 (2) |
C5—C13 | 1.404 (2) | C17—H17 | 0.8986 |
C5—C6 | 1.447 (2) | C18—C19 | 1.385 (2) |
C6—C11 | 1.392 (2) | C18—H18 | 0.9705 |
C6—C7 | 1.405 (3) | C19—C20 | 1.388 (2) |
C7—C8 | 1.370 (3) | C19—C22 | 1.480 (2) |
C7—H7 | 0.9259 | C20—C21 | 1.370 (2) |
C8—C9 | 1.380 (3) | C20—H20 | 1.0165 |
C8—H8 | 0.9977 | C21—H21 | 0.9949 |
C9—C10 | 1.377 (3) | C22—O23 | 1.2160 (17) |
C9—H9 | 0.9857 | C22—C24 | 1.480 (2) |
C10—C11 | 1.387 (2) | C24—H24A | 0.9954 |
C10—H10 | 0.9625 | C24—H24B | 0.9131 |
C11—N12 | 1.397 (2) | C24—H24C | 0.8566 |
C2—C1—C13 | 118.10 (18) | C1—C13—N12 | 129.96 (16) |
C2—C1—H1 | 119.1 | C1—C13—C5 | 121.76 (16) |
C13—C1—H1 | 122.8 | N12—C13—C5 | 108.17 (16) |
C1—C2—C3 | 121.1 (2) | C15—C14—N12 | 127.20 (17) |
C1—C2—H2 | 117.8 | C15—C14—H14 | 112.2 |
C3—C2—H2 | 121.1 | N12—C14—H14 | 120.5 |
C4—C3—C2 | 121.35 (19) | C14—C15—C16 | 125.65 (17) |
C4—C3—H3 | 121.3 | C14—C15—H15 | 118.1 |
C2—C3—H3 | 117.3 | C16—C15—H15 | 116.1 |
C3—C4—C5 | 118.74 (19) | C21—C16—C17 | 118.53 (16) |
C3—C4—H4 | 128.9 | C21—C16—C15 | 119.06 (16) |
C5—C4—H4 | 112.3 | C17—C16—C15 | 122.41 (17) |
C4—C5—C13 | 118.86 (18) | C16—C17—C18 | 120.43 (16) |
C4—C5—C6 | 133.78 (18) | C16—C17—H17 | 128.1 |
C13—C5—C6 | 107.35 (15) | C18—C17—H17 | 111.4 |
C11—C6—C7 | 118.77 (19) | C19—C18—C17 | 120.55 (16) |
C11—C6—C5 | 106.86 (16) | C19—C18—H18 | 119.1 |
C7—C6—C5 | 134.36 (19) | C17—C18—H18 | 120.3 |
C8—C7—C6 | 119.0 (2) | C18—C19—C20 | 117.99 (16) |
C8—C7—H7 | 128.5 | C18—C19—C22 | 119.85 (15) |
C6—C7—H7 | 112.5 | C20—C19—C22 | 122.16 (16) |
C7—C8—C9 | 120.9 (2) | C21—C20—C19 | 121.37 (17) |
C7—C8—H8 | 119.1 | C21—C20—H20 | 119.2 |
C9—C8—H8 | 119.8 | C19—C20—H20 | 119.4 |
C10—C9—C8 | 121.8 (2) | C20—C21—C16 | 121.10 (17) |
C10—C9—H9 | 117.5 | C20—C21—H21 | 119.6 |
C8—C9—H9 | 120.7 | C16—C21—H21 | 119.3 |
C9—C10—C11 | 117.19 (19) | O23—C22—C24 | 119.25 (16) |
C9—C10—H10 | 124.2 | O23—C22—C19 | 120.76 (17) |
C11—C10—H10 | 118.5 | C24—C22—C19 | 119.98 (16) |
C10—C11—C6 | 122.27 (18) | C22—C24—H24A | 113.8 |
C10—C11—N12 | 128.52 (16) | C22—C24—H24B | 114.2 |
C6—C11—N12 | 109.15 (16) | H24A—C24—H24B | 111.7 |
C11—N12—C13 | 108.45 (14) | C22—C24—H24C | 108.8 |
C11—N12—C14 | 123.11 (15) | H24A—C24—H24C | 104.8 |
C13—N12—C14 | 128.30 (15) | H24B—C24—H24C | 102.4 |
C13—C1—C2—C3 | 0.5 (3) | C14—N12—C13—C1 | 0.3 (3) |
C1—C2—C3—C4 | 1.2 (3) | C11—N12—C13—C5 | −0.09 (17) |
C2—C3—C4—C5 | −0.6 (3) | C14—N12—C13—C5 | −175.95 (15) |
C3—C4—C5—C13 | −1.4 (3) | C4—C5—C13—C1 | 3.1 (2) |
C3—C4—C5—C6 | 177.36 (19) | C6—C5—C13—C1 | −175.97 (15) |
C4—C5—C6—C11 | −179.82 (18) | C4—C5—C13—N12 | 179.72 (14) |
C13—C5—C6—C11 | −0.93 (18) | C6—C5—C13—N12 | 0.63 (17) |
C4—C5—C6—C7 | 0.7 (3) | C11—N12—C14—C15 | 149.70 (17) |
C13—C5—C6—C7 | 179.63 (18) | C13—N12—C14—C15 | −35.0 (3) |
C11—C6—C7—C8 | −2.1 (3) | N12—C14—C15—C16 | 178.21 (15) |
C5—C6—C7—C8 | 177.26 (19) | C14—C15—C16—C21 | 169.39 (17) |
C6—C7—C8—C9 | 0.0 (3) | C14—C15—C16—C17 | −11.2 (3) |
C7—C8—C9—C10 | 1.3 (3) | C21—C16—C17—C18 | −1.9 (2) |
C8—C9—C10—C11 | −0.4 (3) | C15—C16—C17—C18 | 178.69 (15) |
C9—C10—C11—C6 | −1.8 (3) | C16—C17—C18—C19 | 1.1 (2) |
C9—C10—C11—N12 | −178.59 (16) | C17—C18—C19—C20 | 0.3 (2) |
C7—C6—C11—C10 | 3.1 (2) | C17—C18—C19—C22 | −179.22 (15) |
C5—C6—C11—C10 | −176.48 (16) | C18—C19—C20—C21 | −0.9 (2) |
C7—C6—C11—N12 | −179.57 (14) | C22—C19—C20—C21 | 178.63 (15) |
C5—C6—C11—N12 | 0.88 (18) | C19—C20—C21—C16 | 0.1 (3) |
C10—C11—N12—C13 | 176.65 (17) | C17—C16—C21—C20 | 1.4 (3) |
C6—C11—N12—C13 | −0.51 (17) | C15—C16—C21—C20 | −179.23 (16) |
C10—C11—N12—C14 | −7.2 (3) | C18—C19—C22—O23 | −0.2 (2) |
C6—C11—N12—C14 | 175.62 (14) | C20—C19—C22—O23 | −179.72 (17) |
C2—C1—C13—N12 | −178.40 (16) | C18—C19—C22—C24 | −179.18 (16) |
C2—C1—C13—C5 | −2.6 (2) | C20—C19—C22—C24 | 1.3 (2) |
C11—N12—C13—C1 | 176.13 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···O23i | 0.99 | 2.57 | 3.554 (2) | 168 |
C10—H10···O23ii | 0.96 | 2.69 | 3.632 (2) | 167 |
C4—H4···Cg3iii | 0.96 | 2.91 | 3.555 (2) | 126 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y+1, −z−1; (iii) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C22H17NO |
Mr | 311.37 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 8.6392 (6), 24.6618 (17), 8.0637 (7) |
β (°) | 103.665 (7) |
V (Å3) | 1669.4 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.45 × 0.2 × 0.1 |
Data collection | |
Diffractometer | KUMA KM4CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10180, 2931, 1618 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.095, 1.09 |
No. of reflections | 2931 |
No. of parameters | 218 |
No. of restraints | 10 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.12 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006)., SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1989).
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···O23i | 0.99 | 2.57 | 3.554 (2) | 168.1 |
C10—H10···O23ii | 0.96 | 2.69 | 3.632 (2) | 167.3 |
C4—H4···Cg3iii | 0.96 | 2.91 | 3.555 (2) | 126.3 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y+1, −z−1; (iii) x, −y+1/2, z+1/2. |
Carbazole and its derivatives are very attractive compounds due to their electroactivity and luminescent properties (Hyun et al.., 2006). The aromatic rings in carbazole-containing compounds form relatively stable radical cations (holes) and many carbazole derivatives have sufficiently high triplet energy to host red, full-color triplet emitters (e.g. Anni et al., 2004). Such properties make them attractive components of light-emitting diodes, and photorefractive materials (Zhang et al., 2004). Very interesting are N-styryl-substituted carbazole derivatives with electron-withdrawing groups (Prukała et al., 2007). The title compound is a part of our studies on styryl-carbazole derivatives.
The molecule of the title compound (Fig. 1) is built of two approximately planar aromatic fragments, connected by the trans N—C=C—C moity (A). The maximum deviation from the mean plane of nine atoms of the carbazole moiety (B) is 0.0354 (16) Å and from the least-squares plane of the phenyl ring (C) - 0.0098 (12) Å. The overall conformation of the molecule (I) can be described by the dihedral angles between these three planar fragments: A/B: 34.26 (13)°, A/C: 11.19 (14)°, B/C: 45.34 (5)°. The molecule of (I) is significantly less twisted that the closely related methoxy-derivative (Prukała et al., 2007), in which the dihedral angle between the carbazole and phenyl planes is 64.29 (4)°. The bond lengths in the central N—C=C—C fragment show the lack of the delocalization (double C=C bond 1.296 (2) Å, single C—C: 1.480 (2) Å, N—C 1.404 (2) Å).
In the crystal structure centrosymmetric dimers generated by hydrogen bond C—H···O (C21—H···O23i , i = 1 - x, 1 - y, -1 - z) (Table 1, Fig. 2) are connected by C10···O23i (i = x, y, 1 + z) into the chains along the direction [001]. Additional C—H···π interaction (Cg3 in Table 1 denotes the middlepoint of the five-membered ring C5, C6, C11, N12) also support these chains.