Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032606/at2332sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032606/at2332Isup2.hkl |
CCDC reference: 657711
The title compound was prepared according to the literature's report (Huang et al., 2003). Single crystals suitable for X-ray analysis were obtained by slow evaporation at 298 K of a mixture solution of dichloromethane and ethyl acetate in volume of 1:5.
All H atoms were positioned geometrically and refined using a riding model. Constrained distances: 0.93Å for Csp2—H. Uiso(H) values were fixed at 1.2Ueq(C).
Recently, a number of organic two-photon induced fluorescent (TPIF) materials have beeen widely investigated because of their various applications, especially in TPIF microscopy (Denk et al., 1990; Helmchen et al., 2002; Zhang et al., 2002). Among the design strategies for TPIF materials, it is reported that introducing a heteroatom into a molecular structure is an efficient way to obtain excellent TPIF molecules because π-deficient and π-excesive heterocycles may act as efficent acceptor and donor moieties, respectively. The title compound, namely tran-2-(p-formylstyryl)benzexazole, consists of atypical A-π-A' structure, where the heterocyclic, styryl and formyl groups are employed as A, π-conjugated and A' moieties, repectively. Here, we present the crystal structure of the title compound, (I).
The molecule of (I) contains a benzexazole ring and a benzene ring which they bounded through a C═C double bond to each other. The terminal benzene ring and benzexazole ring adopt a trans configuration with respect to the central double bond. The whole molecule assumes a planar structure, with an r.m.s deviation of 0.0362 (4) Å. As atom C6 is a bridged atom in benzexazole ring, it has a distorted trigonal geometry, with the C1—C6—N1 [108.9 (3) °] and C5—C6—N1 [131.3 (3) °] angles deviating significantly from ideal sp2 value of 120°. The similar result is also observed for the other bridged C1 atom. As a result of the π-π conjugation, the C7—C8 [1.442 (4) Å] and C9—C10 [1.461 (4) Å] bonds are significantly shorter than the ideal single bonds.
For related literature, see: Denk et al. (1990); Helmchen & Denk (2002); Huang et al. (2003); Zhang et al. (2002).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level. |
C16H11NO2 | Z = 2 |
Mr = 249.26 | F(000) = 260 |
Triclinic, P1 | Dx = 1.346 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.509 (2) Å | Cell parameters from 943 reflections |
b = 7.404 (3) Å | θ = 3.0–26.0° |
c = 14.005 (5) Å | µ = 0.09 mm−1 |
α = 79.885 (6)° | T = 294 K |
β = 80.766 (6)° | Plate, colourless |
γ = 68.565 (7)° | 0.22 × 0.20 × 0.08 mm |
V = 615.1 (4) Å3 |
Bruker SMART CCD area-detector diffractometer | 2147 independent reflections |
Radiation source: fine-focus sealed tube | 1248 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 25.0°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→7 |
Tmin = 0.981, Tmax = 0.993 | k = −8→7 |
3147 measured reflections | l = −16→16 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.193 | H-atom parameters constrained |
S = 1.18 | w = 1/[σ2(Fo2) + (0.0705P)2 + 0.2468P] where P = (Fo2 + 2Fc2)/3 |
2147 reflections | (Δ/σ)max = 0.001 |
172 parameters | Δρmax = 0.69 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C16H11NO2 | γ = 68.565 (7)° |
Mr = 249.26 | V = 615.1 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.509 (2) Å | Mo Kα radiation |
b = 7.404 (3) Å | µ = 0.09 mm−1 |
c = 14.005 (5) Å | T = 294 K |
α = 79.885 (6)° | 0.22 × 0.20 × 0.08 mm |
β = 80.766 (6)° |
Bruker SMART CCD area-detector diffractometer | 2147 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1248 reflections with I > 2σ(I) |
Tmin = 0.981, Tmax = 0.993 | Rint = 0.020 |
3147 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.193 | H-atom parameters constrained |
S = 1.18 | Δρmax = 0.69 e Å−3 |
2147 reflections | Δρmin = −0.23 e Å−3 |
172 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 | ||
O1 | 0.0390 (4) | 0.7576 (4) | 0.18636 (16) | 0.0614 (7) | |
O2 | −0.5701 (6) | 0.8461 (5) | −0.3828 (2) | 0.1154 (12) | |
N1 | 0.4016 (5) | 0.6624 (4) | 0.13459 (19) | 0.0626 (8) | |
C1 | 0.1516 (5) | 0.7422 (5) | 0.2649 (2) | 0.0531 (9) | |
C2 | 0.0685 (7) | 0.7789 (7) | 0.3581 (3) | 0.0821 (13) | |
H2 | −0.0829 | 0.8178 | 0.3780 | 0.098* | |
C3 | 0.2213 (7) | 0.7550 (6) | 0.4211 (3) | 0.0776 (12) | |
H3 | 0.1714 | 0.7775 | 0.4855 | 0.093* | |
C4 | 0.4451 (7) | 0.6987 (6) | 0.3918 (3) | 0.0671 (11) | |
H4 | 0.5434 | 0.6837 | 0.4365 | 0.080* | |
C5 | 0.5254 (6) | 0.6646 (6) | 0.2974 (3) | 0.0656 (10) | |
H5 | 0.6765 | 0.6277 | 0.2771 | 0.079* | |
C6 | 0.3727 (5) | 0.6870 (5) | 0.2331 (2) | 0.0503 (8) | |
C7 | 0.2032 (6) | 0.7049 (5) | 0.1118 (2) | 0.0515 (8) | |
C8 | 0.1403 (6) | 0.7046 (5) | 0.0177 (2) | 0.0570 (9) | |
H8 | 0.2536 | 0.6616 | −0.0316 | 0.068* | |
C9 | −0.0657 (6) | 0.7607 (5) | −0.0037 (2) | 0.0542 (9) | |
H9 | −0.1763 | 0.7984 | 0.0474 | 0.065* | |
C10 | −0.1412 (5) | 0.7706 (4) | −0.0978 (2) | 0.0463 (8) | |
C11 | 0.0027 (6) | 0.7232 (6) | −0.1820 (2) | 0.0635 (10) | |
H11 | 0.1551 | 0.6820 | −0.1794 | 0.076* | |
C12 | −0.0774 (6) | 0.7366 (6) | −0.2684 (2) | 0.0683 (11) | |
H12 | 0.0220 | 0.7048 | −0.3237 | 0.082* | |
C13 | −0.3023 (6) | 0.7960 (5) | −0.2757 (2) | 0.0527 (9) | |
C14 | −0.4468 (6) | 0.8462 (6) | −0.1935 (2) | 0.0677 (11) | |
H14 | −0.5991 | 0.8896 | −0.1969 | 0.081* | |
C15 | −0.3668 (6) | 0.8325 (6) | −0.1066 (2) | 0.0657 (10) | |
H15 | −0.4671 | 0.8657 | −0.0517 | 0.079* | |
C16 | −0.3789 (7) | 0.8041 (6) | −0.3703 (3) | 0.0742 (12) | |
H16 | −0.2727 | 0.7748 | −0.4237 | 0.089* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0536 (14) | 0.0881 (18) | 0.0465 (14) | −0.0250 (12) | −0.0114 (11) | −0.0122 (12) |
O2 | 0.107 (3) | 0.162 (3) | 0.088 (2) | −0.043 (2) | −0.032 (2) | −0.031 (2) |
N1 | 0.0557 (19) | 0.088 (2) | 0.0449 (18) | −0.0203 (15) | −0.0109 (13) | −0.0166 (15) |
C1 | 0.052 (2) | 0.069 (2) | 0.0400 (18) | −0.0195 (17) | −0.0139 (15) | −0.0052 (16) |
C2 | 0.065 (3) | 0.134 (4) | 0.050 (2) | −0.037 (2) | 0.0000 (19) | −0.019 (2) |
C3 | 0.090 (3) | 0.111 (3) | 0.036 (2) | −0.039 (3) | −0.0101 (19) | −0.010 (2) |
C4 | 0.076 (3) | 0.079 (3) | 0.051 (2) | −0.027 (2) | −0.0269 (19) | −0.0050 (19) |
C5 | 0.055 (2) | 0.085 (3) | 0.056 (2) | −0.0169 (19) | −0.0191 (17) | −0.0127 (19) |
C6 | 0.060 (2) | 0.057 (2) | 0.0340 (17) | −0.0181 (16) | −0.0107 (15) | −0.0060 (14) |
C7 | 0.060 (2) | 0.059 (2) | 0.0375 (18) | −0.0216 (17) | −0.0071 (16) | −0.0062 (15) |
C8 | 0.066 (2) | 0.069 (2) | 0.0406 (19) | −0.0252 (18) | −0.0082 (16) | −0.0112 (16) |
C9 | 0.061 (2) | 0.062 (2) | 0.0416 (19) | −0.0204 (17) | −0.0119 (16) | −0.0080 (15) |
C10 | 0.052 (2) | 0.050 (2) | 0.0389 (18) | −0.0187 (15) | −0.0114 (14) | −0.0033 (14) |
C11 | 0.050 (2) | 0.091 (3) | 0.048 (2) | −0.0175 (18) | −0.0104 (16) | −0.0151 (18) |
C12 | 0.063 (2) | 0.103 (3) | 0.0386 (19) | −0.022 (2) | −0.0054 (16) | −0.0207 (19) |
C13 | 0.060 (2) | 0.065 (2) | 0.0383 (18) | −0.0244 (17) | −0.0130 (15) | −0.0088 (15) |
C14 | 0.053 (2) | 0.104 (3) | 0.052 (2) | −0.031 (2) | −0.0103 (17) | −0.012 (2) |
C15 | 0.058 (2) | 0.099 (3) | 0.043 (2) | −0.029 (2) | −0.0031 (16) | −0.0176 (19) |
C16 | 0.063 (3) | 0.096 (3) | 0.069 (3) | −0.025 (2) | −0.026 (2) | −0.016 (2) |
O1—C7 | 1.365 (4) | C8—C9 | 1.318 (5) |
O1—C1 | 1.383 (4) | C8—H8 | 0.9300 |
O2—C16 | 1.202 (4) | C9—C10 | 1.461 (4) |
N1—C7 | 1.292 (4) | C9—H9 | 0.9300 |
N1—C6 | 1.397 (4) | C10—C15 | 1.389 (5) |
C1—C2 | 1.365 (5) | C10—C11 | 1.393 (4) |
C1—C6 | 1.365 (4) | C11—C12 | 1.367 (5) |
C2—C3 | 1.377 (5) | C11—H11 | 0.9300 |
C2—H2 | 0.9300 | C12—C13 | 1.381 (5) |
C3—C4 | 1.375 (5) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—C14 | 1.377 (5) |
C4—C5 | 1.372 (5) | C13—C16 | 1.473 (5) |
C4—H4 | 0.9300 | C14—C15 | 1.373 (5) |
C5—C6 | 1.393 (4) | C14—H14 | 0.9300 |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
C7—C8 | 1.442 (4) | C16—H16 | 0.9300 |
C7—O1—C1 | 104.0 (2) | C7—C8—H8 | 117.5 |
C7—N1—C6 | 104.7 (3) | C8—C9—C10 | 127.8 (3) |
C2—C1—C6 | 123.2 (3) | C8—C9—H9 | 116.1 |
C2—C1—O1 | 129.0 (3) | C10—C9—H9 | 116.1 |
C6—C1—O1 | 107.7 (3) | C15—C10—C11 | 116.9 (3) |
C1—C2—C3 | 116.3 (4) | C15—C10—C9 | 119.8 (3) |
C1—C2—H2 | 121.8 | C11—C10—C9 | 123.3 (3) |
C3—C2—H2 | 121.8 | C12—C11—C10 | 120.8 (3) |
C4—C3—C2 | 122.0 (3) | C12—C11—H11 | 119.6 |
C4—C3—H3 | 119.0 | C10—C11—H11 | 119.6 |
C2—C3—H3 | 119.0 | C11—C12—C13 | 121.7 (3) |
C5—C4—C3 | 120.8 (3) | C11—C12—H12 | 119.2 |
C5—C4—H4 | 119.6 | C13—C12—H12 | 119.2 |
C3—C4—H4 | 119.6 | C14—C13—C12 | 118.3 (3) |
C4—C5—C6 | 117.8 (3) | C14—C13—C16 | 122.5 (3) |
C4—C5—H5 | 121.1 | C12—C13—C16 | 119.3 (3) |
C6—C5—H5 | 121.1 | C15—C14—C13 | 120.2 (3) |
C1—C6—C5 | 119.8 (3) | C15—C14—H14 | 119.9 |
C1—C6—N1 | 108.9 (3) | C13—C14—H14 | 119.9 |
C5—C6—N1 | 131.3 (3) | C14—C15—C10 | 122.2 (3) |
N1—C7—O1 | 114.7 (3) | C14—C15—H15 | 118.9 |
N1—C7—C8 | 127.1 (3) | C10—C15—H15 | 118.9 |
O1—C7—C8 | 118.2 (3) | O2—C16—C13 | 124.1 (4) |
C9—C8—C7 | 124.9 (3) | O2—C16—H16 | 118.0 |
C9—C8—H8 | 117.5 | C13—C16—H16 | 118.0 |
C7—O1—C1—C2 | 179.6 (4) | C1—O1—C7—C8 | 179.7 (3) |
C7—O1—C1—C6 | 1.5 (3) | N1—C7—C8—C9 | −175.6 (3) |
C6—C1—C2—C3 | −0.8 (6) | O1—C7—C8—C9 | 3.5 (5) |
O1—C1—C2—C3 | −178.6 (4) | C7—C8—C9—C10 | 177.7 (3) |
C1—C2—C3—C4 | 0.5 (6) | C8—C9—C10—C15 | 179.5 (3) |
C2—C3—C4—C5 | 0.2 (6) | C8—C9—C10—C11 | −1.4 (5) |
C3—C4—C5—C6 | −0.6 (6) | C15—C10—C11—C12 | −0.4 (5) |
C2—C1—C6—C5 | 0.4 (6) | C9—C10—C11—C12 | −179.5 (3) |
O1—C1—C6—C5 | 178.6 (3) | C10—C11—C12—C13 | −0.4 (6) |
C2—C1—C6—N1 | −179.7 (4) | C11—C12—C13—C14 | 1.3 (6) |
O1—C1—C6—N1 | −1.5 (4) | C11—C12—C13—C16 | −178.9 (4) |
C4—C5—C6—C1 | 0.3 (5) | C12—C13—C14—C15 | −1.5 (6) |
C4—C5—C6—N1 | −179.6 (3) | C16—C13—C14—C15 | 178.7 (4) |
C7—N1—C6—C1 | 0.8 (4) | C13—C14—C15—C10 | 0.7 (6) |
C7—N1—C6—C5 | −179.3 (4) | C11—C10—C15—C14 | 0.3 (5) |
C6—N1—C7—O1 | 0.2 (4) | C9—C10—C15—C14 | 179.4 (3) |
C6—N1—C7—C8 | 179.3 (3) | C14—C13—C16—O2 | −3.4 (7) |
C1—O1—C7—N1 | −1.1 (4) | C12—C13—C16—O2 | 176.8 (4) |
Experimental details
Crystal data | |
Chemical formula | C16H11NO2 |
Mr | 249.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 6.509 (2), 7.404 (3), 14.005 (5) |
α, β, γ (°) | 79.885 (6), 80.766 (6), 68.565 (7) |
V (Å3) | 615.1 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.22 × 0.20 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.981, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3147, 2147, 1248 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.193, 1.18 |
No. of reflections | 2147 |
No. of parameters | 172 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.69, −0.23 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
C7—C8 | 1.442 (4) | C9—C10 | 1.461 (4) |
C2—C1—O1 | 129.0 (3) | C1—C6—N1 | 108.9 (3) |
C6—C1—O1 | 107.7 (3) | C5—C6—N1 | 131.3 (3) |
C7—C8—C9—C10 | 177.7 (3) |
Recently, a number of organic two-photon induced fluorescent (TPIF) materials have beeen widely investigated because of their various applications, especially in TPIF microscopy (Denk et al., 1990; Helmchen et al., 2002; Zhang et al., 2002). Among the design strategies for TPIF materials, it is reported that introducing a heteroatom into a molecular structure is an efficient way to obtain excellent TPIF molecules because π-deficient and π-excesive heterocycles may act as efficent acceptor and donor moieties, respectively. The title compound, namely tran-2-(p-formylstyryl)benzexazole, consists of atypical A-π-A' structure, where the heterocyclic, styryl and formyl groups are employed as A, π-conjugated and A' moieties, repectively. Here, we present the crystal structure of the title compound, (I).
The molecule of (I) contains a benzexazole ring and a benzene ring which they bounded through a C═C double bond to each other. The terminal benzene ring and benzexazole ring adopt a trans configuration with respect to the central double bond. The whole molecule assumes a planar structure, with an r.m.s deviation of 0.0362 (4) Å. As atom C6 is a bridged atom in benzexazole ring, it has a distorted trigonal geometry, with the C1—C6—N1 [108.9 (3) °] and C5—C6—N1 [131.3 (3) °] angles deviating significantly from ideal sp2 value of 120°. The similar result is also observed for the other bridged C1 atom. As a result of the π-π conjugation, the C7—C8 [1.442 (4) Å] and C9—C10 [1.461 (4) Å] bonds are significantly shorter than the ideal single bonds.