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The title compound, C15H12N2O3, is non-planar, with a dihedral angle of 83.0 (1)° between the two benzene rings. The mol­ecules are linked into a ribbon along the b axis by inter­molecular C—H...O and O—H...N hydrogen bonds. The packing is further stabilized by C—H...π and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029338/is6123sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029338/is6123Isup2.hkl
Contains datablock I

CCDC reference: 287610

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.048
  • wR factor = 0.127
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.58 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C15 H12 N2 O3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

For several decades, much attention has been paid to the search for new nonlinear optical (NLO) materials, because these materials have been widely applied or have great potentials in modern laser technology, optical communication and information storage (Long, 1995). The Schiff base compounds are new organic NLO materials, which have been investigated during recent years because many of them have NLO behavior and are easy to synthesize (Unver et al., 2004; Jalali-Heravi et al., 2000). We have recently prepared the novel push–pull Schiff base, (I), containing benzene rings, and C=N and C=C bonds. We report here its crystal structure (Fig. 1).

The bond lengths and angles are within normal ranges (Allen et al., 1987). The bonds between the two benzene rings show a characteristic intermediate length between single and double bonds because of the conjugated CC and CN double bonds (Table 1). The whole molecule is non-planar, with a dihedral angle of 83.0 (1)° between the two benzene rings. There exists an intramolecular C—H···O hydrogen bond (Table 2), forming a six-membered ring. In the crystal structure, molecules are linked into a ribbon along the b axis by weak C—H···O and O—H···N intermolecular hydrogen bonds (Fig. 2). The packing is further stabilized by C—H···π and ππ interactions involving the benzene rings [Cg1···Cg1(−x, −1 − y, −z) = 3.711 (2) Å, where Cg1 is the centroid of the C1–C6 ring].

Experimental top

To a solution of cinnamaldehyde (13.2 g, 0.1 ml) in acetic anhydride was added concentrated nitric acid (3.6 ml) and acetic acid (12.0 ml) over a period of 3 h under 278 K. The reaction mixture was allowed to stand for 2 d at room temperature. 20% HCl was added and o-nitrocinnamaldehyde was obtained as a yellow solid. To a solution of o-nitrocinnamaldehyde (0.25 g, 1.4 mmol) in water (20 ml) was added a solution of o-aminophenol (0.15 g, 1.4 mmol) in ethanol (20 ml). The mixture was heated under reflux for 4 h, yielding quantities of precipitate. Yellow single crystals suitable for X-ray diffraction study were obtained by slow evaporation of a ethanol solution over a period of 3 d.

Refinement top

All H atoms were located in difference Fourier maps and constrained to ride on their parent atoms, with C—H = 0.93 Å and O—H = 0.82 Å, and with Uiso(H) = 1.2 Ueq(C) and 1.5Ueq(O).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atom numbering scheme. The intramolecular hydrogen bond is shown as a dashed line.
[Figure 2] Fig. 2. Packing diagram of (I), showing the ribbons along the b axis, viewed down the c axis. Hydrogen bonds are shown as dashed lines. Is it possible to provide a figure showing the unit cell?
2-{[3-(2-Nitrophenyl)prop-2-enylidene]amino}phenol top
Crystal data top
C15H12N2O3F(000) = 1120
Mr = 268.27Dx = 1.332 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 22.654 (3) ÅCell parameters from 2347 reflections
b = 7.5464 (10) Åθ = 2.6–25.7°
c = 18.816 (2) ŵ = 0.10 mm1
β = 123.692 (2)°T = 293 K
V = 2676.5 (6) Å3Block, yellow
Z = 80.38 × 0.22 × 0.14 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
2635 independent reflections
Radiation source: fine-focus sealed tube2111 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 2.2°
ω scansh = 1527
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 99
Tmin = 0.965, Tmax = 0.987l = 2322
7282 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0584P)2 + 1.5459P]
where P = (Fo2 + 2Fc2)/3
2635 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C15H12N2O3V = 2676.5 (6) Å3
Mr = 268.27Z = 8
Monoclinic, C2/cMo Kα radiation
a = 22.654 (3) ŵ = 0.10 mm1
b = 7.5464 (10) ÅT = 293 K
c = 18.816 (2) Å0.38 × 0.22 × 0.14 mm
β = 123.692 (2)°
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
2635 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2111 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.987Rint = 0.022
7282 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.127H-atom parameters constrained
S = 1.03Δρmax = 0.29 e Å3
2635 reflectionsΔρmin = 0.28 e Å3
181 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
O10.07054 (13)0.3837 (3)0.25409 (12)0.1329 (10)
O20.01401 (10)0.1927 (2)0.15485 (11)0.0980 (7)
O30.23510 (7)0.28984 (17)0.22499 (8)0.0516 (4)
H3A0.23970.38000.25200.077*
N10.02857 (10)0.3445 (2)0.17952 (11)0.0737 (6)
N20.23660 (8)0.00307 (17)0.14026 (9)0.0402 (3)
C10.00561 (10)0.4880 (2)0.11663 (12)0.0494 (5)
C20.03180 (11)0.6444 (3)0.13574 (14)0.0591 (5)
H2B0.07450.65930.18830.071*
C30.00529 (12)0.7775 (3)0.07628 (15)0.0616 (6)
H3B0.03000.88360.08820.074*
C40.05816 (12)0.7537 (3)0.00132 (15)0.0595 (5)
H4A0.07570.84290.04230.071*
C50.09587 (11)0.5978 (2)0.01842 (12)0.0506 (5)
H5A0.13900.58510.07060.061*
C60.07124 (9)0.4598 (2)0.04000 (11)0.0427 (4)
C70.11460 (10)0.3009 (2)0.02192 (11)0.0463 (4)
H7A0.11080.24360.06810.056*
C80.15892 (10)0.2323 (2)0.05506 (11)0.0459 (4)
H8A0.16370.28750.10220.055*
C90.19985 (10)0.0750 (2)0.06799 (11)0.0442 (4)
H9A0.19950.02850.02200.053*
C100.27698 (9)0.1542 (2)0.14842 (9)0.0367 (4)
C110.27845 (9)0.2986 (2)0.19625 (10)0.0386 (4)
C120.32100 (10)0.4434 (2)0.20983 (11)0.0465 (4)
H12A0.32130.54020.24070.056*
C130.36290 (11)0.4447 (3)0.17777 (12)0.0540 (5)
H13A0.39210.54130.18810.065*
C140.36174 (11)0.3038 (3)0.13052 (13)0.0534 (5)
H14A0.38990.30560.10870.064*
C150.31875 (10)0.1601 (2)0.11559 (11)0.0453 (4)
H15A0.31770.06580.08310.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1347 (18)0.0890 (14)0.0603 (11)0.0286 (13)0.0174 (12)0.0035 (10)
O20.1024 (14)0.0484 (9)0.0769 (12)0.0056 (9)0.0085 (10)0.0037 (8)
O30.0602 (8)0.0528 (7)0.0505 (8)0.0083 (6)0.0361 (7)0.0128 (6)
N10.0656 (12)0.0568 (11)0.0512 (11)0.0058 (9)0.0027 (9)0.0007 (9)
N20.0439 (8)0.0380 (7)0.0360 (7)0.0024 (6)0.0205 (7)0.0026 (6)
C10.0491 (11)0.0436 (10)0.0464 (10)0.0024 (8)0.0208 (9)0.0079 (8)
C20.0512 (12)0.0518 (11)0.0663 (13)0.0100 (9)0.0276 (11)0.0163 (10)
C30.0668 (14)0.0429 (10)0.0879 (16)0.0114 (10)0.0508 (14)0.0114 (10)
C40.0758 (15)0.0442 (10)0.0739 (14)0.0062 (10)0.0511 (13)0.0080 (10)
C50.0525 (11)0.0470 (10)0.0477 (10)0.0026 (9)0.0250 (9)0.0004 (8)
C60.0453 (10)0.0387 (9)0.0427 (9)0.0011 (7)0.0236 (8)0.0059 (7)
C70.0518 (11)0.0419 (9)0.0395 (9)0.0033 (8)0.0218 (9)0.0019 (8)
C80.0503 (11)0.0435 (9)0.0396 (9)0.0040 (8)0.0221 (9)0.0027 (7)
C90.0485 (10)0.0448 (9)0.0359 (9)0.0027 (8)0.0214 (8)0.0004 (7)
C100.0386 (9)0.0360 (8)0.0286 (8)0.0002 (7)0.0143 (7)0.0027 (6)
C110.0405 (9)0.0404 (9)0.0305 (8)0.0028 (7)0.0171 (7)0.0027 (7)
C120.0554 (11)0.0379 (9)0.0411 (10)0.0037 (8)0.0235 (9)0.0022 (7)
C130.0599 (12)0.0476 (10)0.0530 (11)0.0150 (9)0.0304 (10)0.0010 (9)
C140.0569 (12)0.0579 (11)0.0548 (11)0.0051 (9)0.0369 (10)0.0009 (9)
C150.0510 (11)0.0449 (9)0.0423 (10)0.0002 (8)0.0273 (9)0.0036 (8)
Geometric parameters (Å, º) top
O1—N11.217 (2)C6—C71.466 (2)
O2—N11.211 (2)C7—C81.327 (2)
O3—C111.360 (2)C7—H7A0.9300
O3—H3A0.8200C8—C91.442 (2)
N1—C11.468 (3)C8—H8A0.9300
N2—C91.278 (2)C9—H9A0.9300
N2—C101.416 (2)C10—C151.388 (2)
C1—C21.380 (3)C10—C111.402 (2)
C1—C61.399 (3)C11—C121.384 (2)
C2—C31.369 (3)C12—C131.379 (3)
C2—H2B0.9300C12—H12A0.9300
C3—C41.379 (3)C13—C141.377 (3)
C3—H3B0.9300C13—H13A0.9300
C4—C51.383 (3)C14—C151.379 (3)
C4—H4A0.9300C14—H14A0.9300
C5—C61.387 (2)C15—H15A0.9300
C5—H5A0.9300
C11—O3—H3A109.5C6—C7—H7A117.4
O2—N1—O1123.0 (2)C7—C8—C9122.13 (17)
O2—N1—C1118.61 (17)C7—C8—H8A118.9
O1—N1—C1118.39 (19)C9—C8—H8A118.9
C9—N2—C10119.13 (14)N2—C9—C8122.51 (16)
C2—C1—C6123.14 (18)N2—C9—H9A118.7
C2—C1—N1116.61 (17)C8—C9—H9A118.7
C6—C1—N1120.18 (16)C15—C10—C11118.77 (15)
C3—C2—C1119.14 (19)C15—C10—N2122.44 (14)
C3—C2—H2B120.4C11—C10—N2118.65 (14)
C1—C2—H2B120.4O3—C11—C12123.19 (15)
C2—C3—C4119.79 (18)O3—C11—C10116.88 (14)
C2—C3—H3B120.1C12—C11—C10119.90 (15)
C4—C3—H3B120.1C13—C12—C11120.18 (16)
C3—C4—C5120.23 (19)C13—C12—H12A119.9
C3—C4—H4A119.9C11—C12—H12A119.9
C5—C4—H4A119.9C14—C13—C12120.40 (17)
C4—C5—C6121.96 (19)C14—C13—H13A119.8
C4—C5—H5A119.0C12—C13—H13A119.8
C6—C5—H5A119.0C13—C14—C15119.84 (17)
C5—C6—C1115.67 (16)C13—C14—H14A120.1
C5—C6—C7120.47 (16)C15—C14—H14A120.1
C1—C6—C7123.77 (16)C14—C15—C10120.89 (16)
C8—C7—C6125.20 (17)C14—C15—H15A119.6
C8—C7—H7A117.4C10—C15—H15A119.6
O2—N1—C1—C2151.9 (2)C6—C7—C8—C9179.85 (17)
O1—N1—C1—C227.8 (3)C10—N2—C9—C8178.23 (15)
O2—N1—C1—C625.1 (3)C7—C8—C9—N2172.11 (18)
O1—N1—C1—C6155.2 (2)C9—N2—C10—C1545.4 (2)
C6—C1—C2—C32.4 (3)C9—N2—C10—C11138.87 (17)
N1—C1—C2—C3174.52 (19)C15—C10—C11—O3178.01 (14)
C1—C2—C3—C40.2 (3)N2—C10—C11—O36.1 (2)
C2—C3—C4—C51.6 (3)C15—C10—C11—C120.1 (2)
C3—C4—C5—C61.3 (3)N2—C10—C11—C12175.92 (15)
C4—C5—C6—C10.7 (3)O3—C11—C12—C13179.00 (16)
C4—C5—C6—C7176.22 (17)C10—C11—C12—C131.2 (3)
C2—C1—C6—C52.6 (3)C11—C12—C13—C141.4 (3)
N1—C1—C6—C5174.21 (17)C12—C13—C14—C150.4 (3)
C2—C1—C6—C7174.24 (18)C13—C14—C15—C100.7 (3)
N1—C1—C6—C79.0 (3)C11—C10—C15—C140.9 (2)
C5—C6—C7—C832.7 (3)N2—C10—C15—C14174.80 (16)
C1—C6—C7—C8150.64 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···N2i0.822.012.761 (2)151
C7—H7A···O20.932.382.707 (3)100
C12—H12A···O3i0.932.553.418 (2)155
C2—H2B···Cg2ii0.932.693.591 (2)162
C14—H14A···Cg1iii0.932.803.628 (3)149
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y1/2, z1/2; (iii) x+1/2, y1/2, z.

Experimental details

Crystal data
Chemical formulaC15H12N2O3
Mr268.27
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)22.654 (3), 7.5464 (10), 18.816 (2)
β (°) 123.692 (2)
V3)2676.5 (6)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.38 × 0.22 × 0.14
Data collection
DiffractometerSiemens SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.965, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
7282, 2635, 2111
Rint0.022
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.127, 1.03
No. of reflections2635
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.28

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Selected bond lengths (Å) top
O1—N11.217 (2)N2—C91.278 (2)
O2—N11.211 (2)N2—C101.416 (2)
O3—C111.360 (2)C7—C81.327 (2)
N1—C11.468 (3)C8—C91.442 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···N2i0.822.012.761 (2)151
C7—H7A···O20.932.382.707 (3)100
C12—H12A···O3i0.932.553.418 (2)155
C2—H2B···Cg2ii0.932.693.591 (2)162
C14—H14A···Cg1iii0.932.803.628 (3)149
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y1/2, z1/2; (iii) x+1/2, y1/2, z.
 

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