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In the crystal structure of the title compound, C19H14N2O2, the mol­ecules are almost planar. The dihedral angle between the two aromatic ring systems is 3.67 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022453/nc2032sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022453/nc2032Isup2.hkl
Contains datablock I

CCDC reference: 651451

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.047
  • wR factor = 0.124
  • Data-to-parameter ratio = 14.0

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 ....... ?
Alert level G 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 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 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 0 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

Comment top

As part of our ongoing studies on push-pull Schiff bases, the title compound was synthesized and its crystal structure was determined (Yang et al., 2006).

The molecule is almost planar with a dihedral angle of 3.67 (1)° between the two aromatic rings (Fig. 1). As expected, the bond lengths between the benzene and naphthalene rings in (I) alternates. In the crystal structure the molecules are stacked onto each other with distances of 3.782 and 3.731 Å between the centroids of the rings, indicating for π-π interactions.

Related literature top

For related literature, see: Yang et al. (2006).

Experimental top

Compound (I) was prepared according to the method of Yang et al. (2006). Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of the solvent from an ethanol-water (4:1 v/v) solution over a period of 3 d.

Refinement top

The H atoms were positioned with idealized geometry and were refined isotropic with Uiso(H) = 1.2 Ueq(C) using a riding model with C—H distances of 0.93 Å.

Structure description top

As part of our ongoing studies on push-pull Schiff bases, the title compound was synthesized and its crystal structure was determined (Yang et al., 2006).

The molecule is almost planar with a dihedral angle of 3.67 (1)° between the two aromatic rings (Fig. 1). As expected, the bond lengths between the benzene and naphthalene rings in (I) alternates. In the crystal structure the molecules are stacked onto each other with distances of 3.782 and 3.731 Å between the centroids of the rings, indicating for π-π interactions.

For related literature, see: Yang et al. (2006).

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 (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. Crystal structure of I showing 50% probability displacement ellipsoids and the atom numbering scheme.
N-[3-(2-Nitrophenyl)allylidene]naphthalen-1-amine top
Crystal data top
C19H14N2O2F(000) = 632
Mr = 302.32Dx = 1.352 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.440 (2) ÅCell parameters from 1605 reflections
b = 7.4165 (10) Åθ = 2.8–23.8°
c = 14.598 (2) ŵ = 0.09 mm1
β = 117.347 (2)°T = 293 K
V = 1484.7 (3) Å3Plate, yellow
Z = 40.42 × 0.26 × 0.05 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
2913 independent reflections
Radiation source: fine-focus sealed tube2014 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Detector resolution: 8.33 pixels mm-1θmax = 26.1°, θmin = 1.5°
ω scansh = 1912
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 98
Tmin = 0.964, Tmax = 0.996l = 1817
8073 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0587P)2 + 0.0855P]
where P = (Fo2 + 2Fc2)/3
2913 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C19H14N2O2V = 1484.7 (3) Å3
Mr = 302.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.440 (2) ŵ = 0.09 mm1
b = 7.4165 (10) ÅT = 293 K
c = 14.598 (2) Å0.42 × 0.26 × 0.05 mm
β = 117.347 (2)°
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
2913 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2014 reflections with I > 2σ(I)
Tmin = 0.964, Tmax = 0.996Rint = 0.039
8073 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 1.03Δρmax = 0.13 e Å3
2913 reflectionsΔρmin = 0.20 e Å3
208 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
C190.18422 (11)0.8023 (2)0.42612 (12)0.0389 (4)
C60.25313 (11)0.6242 (2)0.47210 (13)0.0413 (4)
N20.02462 (10)0.7772 (2)0.41815 (11)0.0487 (4)
N10.40204 (11)0.5240 (2)0.31629 (12)0.0548 (4)
C50.35316 (11)0.5882 (2)0.42333 (12)0.0420 (4)
C100.08469 (11)0.7471 (2)0.37018 (13)0.0417 (4)
C10.21576 (13)0.6856 (2)0.57357 (14)0.0504 (5)
H1A0.14930.70960.61010.061*
C70.18684 (11)0.5971 (2)0.42695 (13)0.0466 (4)
H7A0.19890.50050.38210.056*
C110.05107 (13)0.6791 (2)0.27212 (14)0.0519 (5)
H11A0.01350.64210.23610.062*
C140.24596 (11)0.7850 (2)0.37904 (13)0.0424 (4)
C40.41129 (13)0.6127 (2)0.47087 (15)0.0518 (5)
H4A0.47750.58650.43580.062*
C130.20743 (13)0.7164 (3)0.27765 (14)0.0523 (5)
H13A0.24750.70660.24590.063*
C90.04464 (12)0.6684 (2)0.40303 (14)0.0494 (5)
H9A0.05280.56550.36350.059*
C120.11219 (13)0.6645 (3)0.22567 (14)0.0553 (5)
H12A0.08790.61920.15900.066*
C180.22384 (12)0.8694 (2)0.52798 (13)0.0458 (4)
H18A0.18390.88190.55960.055*
C170.31968 (13)0.9160 (2)0.58045 (14)0.0525 (5)
H17A0.34460.95970.64750.063*
C20.27333 (15)0.7122 (3)0.62153 (15)0.0582 (5)
H2B0.24580.75470.68900.070*
C150.34514 (12)0.8360 (2)0.43613 (15)0.0509 (5)
H15A0.38650.82640.40590.061*
C160.38070 (13)0.8985 (2)0.53407 (15)0.0553 (5)
H16A0.44620.92990.57060.066*
O20.47769 (10)0.4391 (2)0.28762 (11)0.0802 (5)
O10.36607 (10)0.5584 (3)0.25959 (10)0.0848 (5)
C80.11034 (12)0.7017 (2)0.44595 (14)0.0493 (5)
H8A0.09890.80090.48900.059*
C30.37129 (15)0.6760 (3)0.57018 (16)0.0585 (5)
H3A0.41030.69430.60250.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C190.0397 (9)0.0348 (9)0.0434 (9)0.0039 (7)0.0203 (8)0.0073 (7)
C60.0381 (9)0.0376 (9)0.0486 (10)0.0023 (7)0.0203 (8)0.0062 (7)
N20.0363 (8)0.0543 (9)0.0576 (9)0.0043 (7)0.0233 (7)0.0046 (7)
N10.0438 (9)0.0663 (10)0.0467 (9)0.0024 (8)0.0142 (8)0.0057 (8)
C50.0391 (9)0.0423 (9)0.0437 (9)0.0014 (7)0.0183 (8)0.0049 (8)
C100.0359 (9)0.0431 (10)0.0463 (10)0.0052 (7)0.0192 (8)0.0074 (8)
C10.0442 (10)0.0497 (11)0.0519 (11)0.0041 (8)0.0173 (9)0.0010 (8)
C70.0403 (10)0.0476 (10)0.0532 (10)0.0030 (8)0.0225 (8)0.0034 (8)
C110.0397 (10)0.0581 (11)0.0484 (10)0.0003 (8)0.0122 (8)0.0065 (9)
C140.0409 (9)0.0413 (10)0.0469 (10)0.0042 (7)0.0218 (8)0.0086 (8)
C40.0443 (10)0.0515 (11)0.0659 (12)0.0009 (8)0.0306 (10)0.0038 (9)
C130.0552 (11)0.0605 (12)0.0500 (11)0.0076 (9)0.0317 (9)0.0065 (9)
C90.0381 (9)0.0499 (11)0.0596 (11)0.0067 (8)0.0218 (9)0.0063 (9)
C120.0564 (12)0.0661 (13)0.0422 (10)0.0027 (9)0.0215 (9)0.0013 (9)
C180.0492 (10)0.0444 (10)0.0471 (10)0.0002 (8)0.0249 (9)0.0023 (8)
C170.0521 (11)0.0508 (11)0.0471 (10)0.0059 (8)0.0163 (9)0.0005 (9)
C20.0704 (13)0.0532 (12)0.0553 (11)0.0028 (10)0.0325 (10)0.0055 (9)
C150.0421 (10)0.0518 (11)0.0645 (12)0.0020 (8)0.0293 (9)0.0115 (9)
C160.0394 (10)0.0531 (11)0.0640 (12)0.0076 (8)0.0155 (9)0.0065 (9)
O20.0538 (9)0.1017 (12)0.0619 (9)0.0247 (8)0.0067 (7)0.0022 (8)
O10.0686 (10)0.1381 (16)0.0511 (8)0.0080 (9)0.0304 (8)0.0017 (9)
C80.0392 (10)0.0510 (11)0.0589 (11)0.0057 (8)0.0235 (9)0.0062 (9)
C30.0675 (13)0.0547 (12)0.0711 (13)0.0005 (9)0.0472 (11)0.0016 (10)
Geometric parameters (Å, º) top
C19—C181.413 (2)C14—C151.418 (2)
C19—C141.414 (2)C4—C31.371 (3)
C19—C101.429 (2)C4—H4A0.9300
C6—C11.396 (2)C13—C121.364 (2)
C6—C51.398 (2)C13—H13A0.9300
C6—C71.464 (2)C9—C81.438 (2)
N2—C91.275 (2)C9—H9A0.9300
N2—C101.413 (2)C12—H12A0.9300
N1—O11.2171 (18)C18—C171.362 (2)
N1—O21.2192 (18)C18—H18A0.9300
N1—C51.468 (2)C17—C161.396 (2)
C5—C41.376 (2)C17—H17A0.9300
C10—C111.375 (2)C2—C31.371 (3)
C1—C21.375 (2)C2—H2B0.9300
C1—H1A0.9300C15—C161.356 (3)
C7—C81.331 (2)C15—H15A0.9300
C7—H7A0.9300C16—H16A0.9300
C11—C121.396 (2)C8—H8A0.9300
C11—H11A0.9300C3—H3A0.9300
C14—C131.412 (2)
C18—C19—C14118.73 (15)C12—C13—C14120.81 (17)
C18—C19—C10122.28 (15)C12—C13—H13A119.6
C14—C19—C10118.96 (15)C14—C13—H13A119.6
C1—C6—C5115.11 (15)N2—C9—C8121.30 (18)
C1—C6—C7119.26 (15)N2—C9—H9A119.3
C5—C6—C7125.60 (16)C8—C9—H9A119.3
C9—N2—C10120.23 (16)C13—C12—C11120.28 (17)
O1—N1—O2122.65 (17)C13—C12—H12A119.9
O1—N1—C5118.92 (15)C11—C12—H12A119.9
O2—N1—C5118.43 (16)C17—C18—C19120.97 (16)
C4—C5—C6122.82 (16)C17—C18—H18A119.5
C4—C5—N1116.38 (15)C19—C18—H18A119.5
C6—C5—N1120.79 (15)C18—C17—C16120.30 (17)
C11—C10—N2123.64 (15)C18—C17—H17A119.9
C11—C10—C19119.50 (15)C16—C17—H17A119.9
N2—C10—C19116.74 (15)C3—C2—C1120.16 (19)
C2—C1—C6122.55 (17)C3—C2—H2B119.9
C2—C1—H1A118.7C1—C2—H2B119.9
C6—C1—H1A118.7C16—C15—C14121.05 (17)
C8—C7—C6124.28 (17)C16—C15—H15A119.5
C8—C7—H7A117.9C14—C15—H15A119.5
C6—C7—H7A117.9C15—C16—C17120.43 (16)
C10—C11—C12121.18 (16)C15—C16—H16A119.8
C10—C11—H11A119.4C17—C16—H16A119.8
C12—C11—H11A119.4C7—C8—C9123.05 (18)
C13—C14—C19119.25 (15)C7—C8—H8A118.5
C13—C14—C15122.24 (16)C9—C8—H8A118.5
C19—C14—C15118.51 (16)C2—C3—C4119.54 (18)
C3—C4—C5119.81 (17)C2—C3—H3A120.2
C3—C4—H4A120.1C4—C3—H3A120.2
C5—C4—H4A120.1
C1—C6—C5—C40.6 (2)C18—C19—C14—C150.1 (2)
C7—C6—C5—C4178.47 (15)C10—C19—C14—C15178.49 (14)
C1—C6—C5—N1179.58 (15)C6—C5—C4—C30.4 (3)
C7—C6—C5—N12.5 (3)N1—C5—C4—C3178.66 (16)
O1—N1—C5—C4154.51 (17)C19—C14—C13—C121.0 (3)
O2—N1—C5—C425.0 (2)C15—C14—C13—C12178.42 (16)
O1—N1—C5—C624.5 (2)C10—N2—C9—C8176.27 (14)
O2—N1—C5—C6155.98 (16)C14—C13—C12—C110.2 (3)
C9—N2—C10—C1136.7 (2)C10—C11—C12—C130.6 (3)
C9—N2—C10—C19147.33 (16)C14—C19—C18—C170.3 (2)
C18—C19—C10—C11178.51 (16)C10—C19—C18—C17178.06 (15)
C14—C19—C10—C110.2 (2)C19—C18—C17—C160.1 (3)
C18—C19—C10—N25.3 (2)C6—C1—C2—C30.8 (3)
C14—C19—C10—N2176.33 (14)C13—C14—C15—C16178.85 (17)
C5—C6—C1—C21.2 (2)C19—C14—C15—C160.6 (2)
C7—C6—C1—C2179.20 (16)C14—C15—C16—C170.8 (3)
C1—C6—C7—C836.3 (2)C18—C17—C16—C150.4 (3)
C5—C6—C7—C8145.94 (17)C6—C7—C8—C9177.95 (15)
N2—C10—C11—C12175.23 (16)N2—C9—C8—C7175.93 (17)
C19—C10—C11—C120.6 (2)C1—C2—C3—C40.2 (3)
C18—C19—C14—C13179.40 (15)C5—C4—C3—C20.8 (3)
C10—C19—C14—C131.0 (2)

Experimental details

Crystal data
Chemical formulaC19H14N2O2
Mr302.32
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)15.440 (2), 7.4165 (10), 14.598 (2)
β (°) 117.347 (2)
V3)1484.7 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.42 × 0.26 × 0.05
Data collection
DiffractometerSiemens SMART 1000 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.964, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections
8073, 2913, 2014
Rint0.039
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.124, 1.03
No. of reflections2913
No. of parameters208
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.13, 0.20

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

 

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