Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056802/lh2533sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056802/lh2533Isup2.hkl |
CCDC reference: 672930
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.061
- wR factor = 0.163
- Data-to-parameter ratio = 16.0
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.720 1.000 Tmin(prime) and Tmax expected: 0.986 0.986 RR(prime) = 0.720 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.72
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.986 Tmax scaled 0.986 Tmin scaled 0.710 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: William et al. (1949); Domenicano et al. (1975); Allen et al. (1987).
Melting points were determined with a Yanagimoto MP-35 melting-point apparatus and were uncorrected. The 1H NMR spectra were measured with a Bruker DRX (500 MHz) (relative to TMS) spectrometer. The solid state IR spectra were recorded from KBr discs on a Nicolet-170.
A mixture of N, N-bis-2-cyanoethylanilne (10 g, 0.055 mol), powdered aluminium chloride (55 g, 0.422 mol), 30 ml chlorobenzeneand 1.5 ml concentrated hydrochloric acid was vigorously stirred at 433 K for 8 h. After cooling, the red oily mixture was hydrolysed with 200 ml ice water,and distilled in steam to remove chlorobenzene. The residue was recrystallized from ethanol to afford a yellow solid. Yield: 8.5 g (85%); m. p. 415 - 416 K. IR (KBr): ν = 1676 cm-1 (C═O). 1H NMR (500 MHz, CDCl3): δ 2.83–2.86 (t, 4H, 2CH2, J = 7.0 Hz), 3.49–3.52 (t, 4H, 2CH2, J = 7.0 Hz), 6.86–6.89 (t, 1H, ArH, J = 7.5 Hz), 8.11–8.12 (d, 2H, ArH, J = 8.0 Hz). Single crystals suitable for crystallographic analysis were obtained by slow evaporation of a methanol water (4:1 v/v)solution.
H atoms were placed in calculated positions with C—H = 0.93–0.97 Å and included in the refinement in the riding-model approximation with Uiso(H) = 1.2Ueq(C).
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 1999).
Fig. 1. The molecular structure with displacement ellipsoids were drawn at the 30% probability level [symmetry code: (A) x, -y + 1/2, z]. |
C12H11NO2 | F(000) = 424 |
Mr = 201.22 | Dx = 1.357 Mg m−3 |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 7909 reflections |
a = 10.069 (2) Å | θ = 3.3–28.9° |
b = 14.081 (3) Å | µ = 0.09 mm−1 |
c = 6.9452 (14) Å | T = 293 K |
V = 984.7 (3) Å3 | Block, colorless |
Z = 4 | 0.15 × 0.15 × 0.15 mm |
Rigaku Mercury2 diffractometer | 1170 independent reflections |
Radiation source: fine-focus sealed tube | 767 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.086 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 27.5°, θmin = 3.3° |
ω scans | h = −13→13 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −18→18 |
Tmin = 0.720, Tmax = 1.00 | l = −9→9 |
9450 measured reflections |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.076P)2 + 0.0053P] where P = (Fo2 + 2Fc2)/3 |
1170 reflections | (Δ/σ)max < 0.001 |
73 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C12H11NO2 | V = 984.7 (3) Å3 |
Mr = 201.22 | Z = 4 |
Orthorhombic, Pnma | Mo Kα radiation |
a = 10.069 (2) Å | µ = 0.09 mm−1 |
b = 14.081 (3) Å | T = 293 K |
c = 6.9452 (14) Å | 0.15 × 0.15 × 0.15 mm |
Rigaku Mercury2 diffractometer | 1170 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 767 reflections with I > 2σ(I) |
Tmin = 0.720, Tmax = 1.00 | Rint = 0.086 |
9450 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.15 e Å−3 |
1170 reflections | Δρmin = −0.19 e Å−3 |
73 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 | 0.2702 (3) | 0.2500 | 1.2858 (4) | 0.0675 (9) | |
H1A | 0.2326 | 0.2500 | 1.4080 | 0.081* | |
C2 | 0.2983 (2) | 0.16584 (14) | 1.1947 (3) | 0.0578 (6) | |
H2A | 0.2760 | 0.1089 | 1.2545 | 0.069* | |
C3 | 0.35918 (18) | 0.16362 (13) | 1.0158 (2) | 0.0469 (5) | |
C4 | 0.3938 (2) | 0.2500 | 0.9238 (3) | 0.0423 (6) | |
C5 | 0.37694 (18) | 0.07268 (15) | 0.9155 (3) | 0.0529 (5) | |
C6 | 0.4347 (2) | 0.07766 (16) | 0.7178 (3) | 0.0643 (6) | |
H6A | 0.3633 | 0.0809 | 0.6242 | 0.077* | |
H6B | 0.4852 | 0.0203 | 0.6928 | 0.077* | |
C7 | 0.5239 (2) | 0.16269 (14) | 0.6933 (3) | 0.0613 (6) | |
H7A | 0.6025 | 0.1548 | 0.7725 | 0.074* | |
H7B | 0.5521 | 0.1670 | 0.5601 | 0.074* | |
O1 | 0.34091 (15) | −0.00237 (11) | 0.9865 (2) | 0.0714 (5) | |
N1 | 0.4561 (2) | 0.2500 | 0.7476 (3) | 0.0506 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.090 (2) | 0.071 (2) | 0.0412 (15) | 0.000 | 0.0151 (14) | 0.000 |
C2 | 0.0705 (13) | 0.0577 (13) | 0.0450 (11) | −0.0091 (10) | 0.0034 (9) | 0.0066 (9) |
C3 | 0.0479 (10) | 0.0494 (12) | 0.0435 (11) | −0.0025 (7) | −0.0032 (7) | −0.0006 (8) |
C4 | 0.0389 (12) | 0.0524 (16) | 0.0356 (12) | 0.000 | −0.0048 (10) | 0.000 |
C5 | 0.0513 (11) | 0.0526 (12) | 0.0548 (12) | −0.0049 (9) | −0.0075 (9) | −0.0041 (9) |
C6 | 0.0735 (14) | 0.0618 (14) | 0.0576 (12) | 0.0065 (11) | −0.0012 (10) | −0.0175 (9) |
C7 | 0.0589 (12) | 0.0700 (16) | 0.0549 (12) | 0.0059 (10) | 0.0125 (9) | −0.0053 (9) |
O1 | 0.0794 (11) | 0.0532 (10) | 0.0815 (11) | −0.0125 (7) | 0.0014 (7) | −0.0043 (7) |
N1 | 0.0511 (12) | 0.0577 (15) | 0.0429 (12) | 0.000 | 0.0085 (9) | 0.000 |
C1—C2i | 1.373 (2) | C5—O1 | 1.221 (2) |
C1—C2 | 1.373 (2) | C5—C6 | 1.493 (3) |
C1—H1A | 0.9300 | C6—C7 | 1.506 (3) |
C2—C3 | 1.386 (3) | C6—H6A | 0.9700 |
C2—H2A | 0.9300 | C6—H6B | 0.9700 |
C3—C4 | 1.417 (2) | C7—N1 | 1.456 (2) |
C3—C5 | 1.469 (3) | C7—H7A | 0.9700 |
C4—N1 | 1.376 (3) | C7—H7B | 0.9700 |
C4—C3i | 1.417 (2) | N1—C7i | 1.456 (2) |
C2i—C1—C2 | 119.4 (2) | C3—C5—C6 | 116.30 (18) |
C2i—C1—H1A | 120.3 | C5—C6—C7 | 111.92 (16) |
C2—C1—H1A | 120.3 | C5—C6—H6A | 109.2 |
C1—C2—C3 | 121.6 (2) | C7—C6—H6A | 109.2 |
C1—C2—H2A | 119.2 | C5—C6—H6B | 109.2 |
C3—C2—H2A | 119.2 | C7—C6—H6B | 109.2 |
C2—C3—C4 | 119.56 (18) | H6A—C6—H6B | 107.9 |
C2—C3—C5 | 119.94 (18) | N1—C7—C6 | 111.27 (17) |
C4—C3—C5 | 120.29 (16) | N1—C7—H7A | 109.4 |
N1—C4—C3i | 120.87 (11) | C6—C7—H7A | 109.4 |
N1—C4—C3 | 120.87 (11) | N1—C7—H7B | 109.4 |
C3i—C4—C3 | 118.2 (2) | C6—C7—H7B | 109.4 |
O1—C5—C3 | 121.77 (18) | H7A—C7—H7B | 108.0 |
O1—C5—C6 | 121.85 (19) |
Symmetry code: (i) x, −y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O1ii | 0.93 | 2.50 | 3.372 (3) | 157 |
C6—H6A···O1iii | 0.97 | 2.52 | 3.377 (3) | 147 |
Symmetry codes: (ii) −x+1/2, −y, z+1/2; (iii) −x+1/2, −y, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C12H11NO2 |
Mr | 201.22 |
Crystal system, space group | Orthorhombic, Pnma |
Temperature (K) | 293 |
a, b, c (Å) | 10.069 (2), 14.081 (3), 6.9452 (14) |
V (Å3) | 984.7 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.15 × 0.15 × 0.15 |
Data collection | |
Diffractometer | Rigaku Mercury2 diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2005) |
Tmin, Tmax | 0.720, 1.00 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9450, 1170, 767 |
Rint | 0.086 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.163, 1.10 |
No. of reflections | 1170 |
No. of parameters | 73 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.19 |
Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O1i | 0.93 | 2.50 | 3.372 (3) | 157 |
C6—H6A···O1ii | 0.97 | 2.52 | 3.377 (3) | 147 |
Symmetry codes: (i) −x+1/2, −y, z+1/2; (ii) −x+1/2, −y, z−1/2. |
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The title compound, belongs to a class of 4-dihydroquinolinone derivatives (William, et al.,1949), which have hitherto received relatively little attention. We have recently found that the title compound undergoes two-photon absorption and two-photon excited fluorescence and is therefore of interest in the study of non-linear optics. An X-ray crystal structure determination of was undertaken in order to elucidate the conformation, and the results are presented here.
The bond lengths observed in the phenyl rings is comparable with average values reported in the literature (Domenicano et al.,1975; Allen et al., 1987). Atom C7 deviates by 0.493 (2) Å from the benzene ring. The mean plane through atoms O1/C5/C6 is twisted from the plane of the benzene ring by 7.5 (2) °, while in acetophenone the acetyl group is essentially co-planar with benzene ring. This twist is most likely due to the strain imposed by sp3-hybridized atoms C6 and C7 in the adjacent ring. The N atom lies approximately in the plane of the benzene ring with a deviation of 0.023 (2) Å, as might be expected for maximum conjugation normally found for N atom substituents on benzene rings. Weak intermolecular C—H···O hydrogen bonds help stabilize the crystal structure.