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ISSN: 2056-9890

(E)-N-[(E)-3-(4-Nitro­phen­yl)allyl­­idene]naphthalen-1-amine

aChemical Kinomics Research Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, bAdvanced Analysis Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, and cCenter for Neuro-Medicine, Brain Science Institute, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea
*Correspondence e-mail: j9601@kist.re.kr

(Received 28 February 2013; accepted 6 March 2013; online 16 March 2013)

In the title compound, C19H14N2O2, the dihedral angle between the mean planes of the 4-nitro­phenyl ring and the naphthalene ring system is 12.79 (2)°. The imine group displays a C—C—N=C torsion angle of 41.0 (2)° and the C=N group has an E conformation. In the crystal, weak C—H⋯O hydrogen bonds link molecules into layers parallel to the b axis.

Related literature

For the synthesis and biological activity of naphthalene compounds, see: Upadhayaya et al. (2010[Upadhayaya, R. S., Vandavasi, J. K., Kardile, R. A., Lahore, S. V., Dixit, S. S., Deokar, H. S., Shinde, P. D., Sarmah, M. P. & Chattopadhyaya, J. (2010). Eur. J. Med. Chem. 2, 1854-1867.]); Rokade & Sayyed (2009[Rokade, Y. B. & Sayyed, R. Z. (2009). RASAYAN J. Chem. 2, 972-980.]). For a related structure, see: Yang et al. (2012[Yang, P., Ding, B. & Du, G.-X. (2012). Acta Cryst. E68, o2966.]).

[Scheme 1]

Experimental

Crystal data
  • C19H14N2O2

  • Mr = 302.33

  • Monoclinic, P 21 /c

  • a = 7.7021 (5) Å

  • b = 13.8713 (12) Å

  • c = 14.2554 (10) Å

  • β = 98.096 (2)°

  • V = 1507.8 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.20 × 0.20 × 0.10 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Rigaku, 1995[Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.714, Tmax = 0.991

  • 14376 measured reflections

  • 3426 independent reflections

  • 1824 reflections with F2 > 2σ(F2)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.125

  • S = 1.00

  • 3426 reflections

  • 220 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C5—H5⋯O1i 0.93 2.66 3.422 (3) 139
C15—H15⋯O2ii 0.93 2.46 3.326 (3) 155
Symmetry codes: (i) x-1, y, z+1; (ii) x-1, y, z.

Data collection: RAPID-AUTO (Rigaku, 2006[Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.

Supporting information


Comment top

Naphthalene derivatives has been identified as new range of potent antimicrobials effective against wide range of human pathogens. They occupy a central place among medicinally important compounds due to their diverse and interesting antibiotic properties with minimum toxicity. (Rokade & Sayyed, 2009; Upadhayaya et al. 2010). In this paper, the title compound was synthesized and characterized by X-ray diffraction. Crystal structure of a similar compound, N-(Naphthalen-1-yl­methyl­idene)-4H-1,2,4-triazol-4-amine, was described previously by Yang et al. (2012).

In the title compound (Fig. 1), C19H14N2O2, the dihedral angle between the mean planes of the 4-nitrophenyl ring (C14—C19) and the naphthalene ring (C1—C10) is 12.79 (2)°. The imine group displays a torsion angle [C1–C10–N1–C11 = 41.0 (2)°] and the imine [C11 = N1] group has an (E) configuration. In the crystal, weak intermolecular C—H···O hydrogen bonds link molecules into layers parallel to the b axis.

Related literature top

For the synthesis and biological activity of naphthalene compounds, see: Upadhayaya et al. (2010); Rokade & Sayyed (2009). For a related structure, see: Yang et al. (2012).

Experimental top

To a solution of 1-naphthylamine (2.0 mmol) in anhydrous ethanol (40 ml) was treated with equimolar quantities of substituted 4-nitrocinnamaldehydes. The mixture was refluxed for 3 days, and the progress of reaction was monitored by TLC. After completion of reaction, the solvent was removed under reduced pressure. The residue was purified by flash column chromatography to afford the title compound as a yellow solid in yield 88%. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethanol at room temperature.

Refinement top

All hydrogen atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.98 Å and Uiso(H) = 1.2 or 1.5 Ueq(C).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 1995); data reduction: RAPID-AUTO (Rigaku, 1995); program(s) used to solve structure: Il Milione (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing the atomic numbering and 50% probability displacement ellipsoid.
(E)-N-[(E)-3-(4-Nitrophenyl)allylidene]naphthalen-1-amine top
Crystal data top
C19H14N2O2F(000) = 632.00
Mr = 302.33Dx = 1.332 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybcCell parameters from 7945 reflections
a = 7.7021 (5) Åθ = 3.1–27.5°
b = 13.8713 (12) ŵ = 0.09 mm1
c = 14.2554 (10) ÅT = 296 K
β = 98.096 (2)°Chunk, yellow
V = 1507.8 (2) Å30.20 × 0.20 × 0.10 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1824 reflections with F2 > 2σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.038
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
h = 89
Tmin = 0.714, Tmax = 0.991k = 1817
14376 measured reflectionsl = 1818
3426 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0632P)2]
where P = (Fo2 + 2Fc2)/3
3426 reflections(Δ/σ)max < 0.001
220 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.24 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C19H14N2O2V = 1507.8 (2) Å3
Mr = 302.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.7021 (5) ŵ = 0.09 mm1
b = 13.8713 (12) ÅT = 296 K
c = 14.2554 (10) Å0.20 × 0.20 × 0.10 mm
β = 98.096 (2)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3426 independent reflections
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
1824 reflections with F2 > 2σ(F2)
Tmin = 0.714, Tmax = 0.991Rint = 0.038
14376 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.16 e Å3
3426 reflectionsΔρmin = 0.24 e Å3
220 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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.83231 (18)0.69908 (11)0.01889 (9)0.0893 (5)
O21.04049 (17)0.66549 (11)0.13076 (10)0.0912 (5)
N10.28674 (17)0.58150 (9)0.58185 (9)0.0559 (4)
N20.8861 (2)0.68108 (10)0.10197 (11)0.0639 (4)
C10.0251 (2)0.57846 (11)0.60108 (11)0.0571 (4)
C20.1560 (2)0.57496 (12)0.65987 (13)0.0646 (5)
C30.1124 (3)0.57509 (12)0.75554 (13)0.0650 (5)
C40.0649 (2)0.57721 (10)0.79753 (11)0.0531 (4)
C50.1143 (3)0.57601 (12)0.89707 (12)0.0656 (5)
C60.2852 (3)0.57557 (13)0.93612 (12)0.0708 (5)
C70.4176 (3)0.57612 (12)0.87819 (12)0.0667 (5)
C80.3764 (2)0.57776 (11)0.78197 (11)0.0566 (4)
C90.19908 (19)0.57918 (10)0.73900 (10)0.0478 (4)
C100.1495 (2)0.58192 (10)0.63815 (10)0.0493 (4)
C110.2713 (3)0.63110 (12)0.50566 (11)0.0548 (4)
C120.4042 (3)0.62977 (12)0.44420 (11)0.0560 (4)
C130.3893 (3)0.67568 (12)0.36151 (11)0.0548 (4)
C140.5200 (2)0.67695 (10)0.29619 (10)0.0486 (4)
C150.4674 (2)0.69629 (11)0.20060 (10)0.0562 (4)
C160.5861 (2)0.69706 (11)0.13708 (11)0.0546 (4)
C170.75962 (19)0.67906 (10)0.16958 (10)0.0494 (4)
C180.8178 (2)0.66060 (11)0.26364 (11)0.0571 (5)
C190.6975 (2)0.65988 (11)0.32628 (11)0.0562 (4)
H10.05680.57840.53570.0685*
H20.27330.57250.63330.0775*
H30.20050.57380.79390.0780*
H50.02770.57550.93640.0787*
H60.31460.57491.00170.0850*
H70.53460.57540.90550.0801*
H80.46550.57790.74420.0679*
H150.34980.70890.17930.0674*
H160.54970.70950.07320.0655*
H180.93590.64890.28430.0686*
H190.73530.64780.39010.0674*
H130.284 (3)0.7118 (12)0.3417 (11)0.064 (5)*
H120.507 (3)0.5928 (12)0.4638 (12)0.072 (6)*
H110.169 (3)0.6735 (11)0.4877 (11)0.062 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0896 (10)0.1221 (13)0.0611 (8)0.0165 (8)0.0280 (8)0.0112 (8)
O20.0506 (8)0.1242 (12)0.1018 (11)0.0034 (8)0.0215 (8)0.0112 (9)
N10.0591 (8)0.0612 (9)0.0492 (8)0.0021 (7)0.0141 (7)0.0007 (7)
N20.0625 (10)0.0652 (10)0.0666 (10)0.0003 (8)0.0182 (8)0.0005 (8)
C10.0591 (10)0.0585 (10)0.0523 (9)0.0027 (8)0.0032 (8)0.0049 (8)
C20.0506 (10)0.0699 (12)0.0729 (12)0.0021 (9)0.0070 (9)0.0074 (9)
C30.0546 (10)0.0716 (12)0.0732 (12)0.0002 (9)0.0235 (9)0.0052 (9)
C40.0587 (10)0.0492 (9)0.0541 (10)0.0008 (7)0.0171 (8)0.0025 (7)
C50.0788 (13)0.0671 (11)0.0552 (10)0.0008 (10)0.0247 (10)0.0015 (9)
C60.0938 (15)0.0728 (12)0.0456 (9)0.0023 (11)0.0087 (10)0.0031 (8)
C70.0653 (11)0.0727 (12)0.0591 (10)0.0018 (9)0.0020 (9)0.0068 (9)
C80.0553 (10)0.0576 (10)0.0572 (10)0.0014 (8)0.0094 (8)0.0050 (8)
C90.0510 (9)0.0427 (8)0.0506 (9)0.0012 (7)0.0099 (8)0.0001 (7)
C100.0545 (9)0.0465 (9)0.0483 (9)0.0029 (7)0.0116 (8)0.0019 (7)
C110.0607 (10)0.0556 (10)0.0487 (9)0.0012 (9)0.0103 (8)0.0024 (8)
C120.0608 (11)0.0573 (10)0.0510 (10)0.0006 (9)0.0116 (9)0.0004 (8)
C130.0578 (10)0.0553 (10)0.0518 (10)0.0021 (8)0.0096 (8)0.0003 (8)
C140.0532 (9)0.0456 (9)0.0469 (9)0.0002 (7)0.0064 (7)0.0010 (7)
C150.0486 (9)0.0686 (11)0.0504 (9)0.0068 (8)0.0040 (8)0.0046 (8)
C160.0551 (10)0.0633 (10)0.0444 (9)0.0030 (8)0.0039 (8)0.0037 (8)
C170.0494 (9)0.0478 (9)0.0525 (9)0.0008 (7)0.0121 (8)0.0011 (7)
C180.0479 (9)0.0620 (11)0.0594 (10)0.0011 (8)0.0003 (8)0.0054 (8)
C190.0580 (10)0.0645 (11)0.0437 (9)0.0002 (8)0.0014 (8)0.0050 (8)
Geometric parameters (Å, º) top
O1—N21.224 (2)C14—C191.395 (3)
O2—N21.222 (2)C15—C161.375 (3)
N1—C101.414 (3)C16—C171.374 (2)
N1—C111.277 (2)C17—C181.377 (2)
N2—C171.464 (3)C18—C191.374 (3)
C1—C21.400 (3)C1—H10.930
C1—C101.375 (2)C2—H20.930
C2—C31.358 (3)C3—H30.930
C3—C41.412 (3)C5—H50.930
C4—C51.416 (3)C6—H60.930
C4—C91.417 (3)C7—H70.930
C5—C61.355 (3)C8—H80.930
C6—C71.400 (3)C11—H110.989 (16)
C7—C81.364 (3)C12—H120.953 (17)
C8—C91.416 (2)C13—H130.959 (17)
C9—C101.435 (2)C15—H150.930
C11—C121.438 (3)C16—H160.930
C12—C131.330 (3)C18—H180.930
C13—C141.464 (3)C19—H190.930
C14—C151.392 (2)
O1···C162.708 (3)C7···H13viii3.134 (17)
O1···C183.547 (2)C8···H3v3.2394
O2···C163.540 (2)C8···H15viii3.2947
O2···C182.729 (3)C8···H13viii3.148 (17)
N1···C82.840 (2)C9···H15viii3.3151
N1···C133.591 (3)C9···H18iv3.3321
C1···C42.789 (3)C9···H13viii3.272 (16)
C1···C112.910 (3)C10···H1xi3.3316
C2···C92.808 (2)C10···H15viii3.2996
C3···C102.798 (3)C10···H18iv3.4799
C4···C72.797 (3)C10···H19iv3.3466
C5···C82.775 (3)C11···H1xi3.3541
C6···C92.795 (3)C11···H2xi3.4512
C9···C113.523 (3)C11···H15viii3.3164
C12···C193.029 (3)C11···H16viii3.1354
C14···C172.758 (3)C11···H12iv3.540 (17)
C15···C182.767 (3)C12···H2v3.4901
C16···C192.761 (3)C12···H2xi3.1301
O1···C1i3.426 (3)C12···H16viii3.0046
O1···C5ii3.422 (3)C12···H12iv3.386 (17)
O1···C19iii3.412 (2)C13···H2xi3.5604
O2···C5iv3.559 (3)C13···H16viii3.4816
O2···C15v3.326 (2)C13···H18ix3.5298
N1···C19iv3.591 (2)C14···H8iv3.5866
N2···C1i3.405 (2)C14···H8iii3.4924
N2···C2i3.509 (3)C15···H6x3.3647
N2···C5iv3.566 (3)C15···H8iii3.1933
C1···O1vi3.426 (3)C16···H2i3.3773
C1···N2vi3.405 (2)C16···H6x3.1359
C2···N2vi3.509 (3)C17···H2i3.4883
C2···C17vi3.480 (3)C19···H1v3.4892
C4···C18iv3.561 (3)H1···O1vi3.2020
C5···O1vii3.422 (3)H1···N1xi3.1668
C5···O2iv3.559 (3)H1···N2vi3.5116
C5···N2iv3.566 (3)H1···C1xi3.0465
C7···C13viii3.456 (3)H1···C10xi3.3316
C8···C14viii3.575 (2)H1···C11xi3.3541
C8···C15viii3.448 (3)H1···C19ix3.4892
C9···C18iv3.329 (2)H1···H1xi2.6052
C9···C19iv3.564 (3)H1···H19ix2.6192
C10···C19iv3.567 (2)H1···H12ix3.3760
C13···C7iii3.456 (3)H2···N1ix3.3669
C14···C8iii3.575 (2)H2···C11xi3.4512
C15···O2ix3.326 (2)H2···C12ix3.4901
C15···C8iii3.448 (3)H2···C12xi3.1301
C17···C2i3.480 (3)H2···C13xi3.5604
C18···C4iv3.561 (3)H2···C16vi3.3773
C18···C9iv3.329 (2)H2···C17vi3.4883
C19···O1viii3.412 (2)H2···H8ix2.7294
C19···N1iv3.591 (2)H2···H16vi3.3765
C19···C9iv3.564 (3)H2···H12ix2.7617
C19···C10iv3.567 (2)H2···H12xi3.1167
O1···H162.4154H3···C7ix3.3298
O2···H182.4477H3···C8ix3.2394
N1···H12.6358H3···H7ix2.7580
N1···H82.5219H3···H8ix2.5703
N1···H122.558 (19)H5···O1vii2.6614
N2···H162.5955H5···O2vii3.0276
N2···H182.6122H5···O2iv3.4966
C1···H33.2302H5···N2vii3.1031
C1···H112.695 (17)H5···C5xii3.4610
C3···H13.2230H5···H5xii2.8416
C3···H52.6512H5···H6xii3.5690
C4···H23.2486H6···O2vii3.2431
C4···H63.2546H6···C7xiii3.2526
C4···H83.2801H6···C15xiv3.3647
C5···H32.6530H6···C16xiv3.1359
C5···H73.2228H6···H5xii3.5690
C6···H83.2377H6···H6xiii3.5374
C7···H53.2269H6···H7xiii2.6476
C8···H63.2337H6···H15xiv3.1225
C9···H13.2677H6···H16xiv2.6995
C9···H33.2819H7···O1xiv3.1257
C9···H53.2729H7···C6xiii3.2438
C9···H73.2542H7···H3v2.7580
C10···H23.2503H7···H6xiii2.6476
C10···H82.6791H7···H7xiii3.5092
C10···H112.515 (16)H7···H16xiv3.0192
C11···H12.7219H7···H13viii3.5723
C11···H83.5939H8···C2v3.3067
C11···H132.607 (16)H8···C3v3.2321
C12···H192.7779H8···C14iv3.5866
C13···H152.6129H8···C14viii3.4924
C13···H192.6670H8···C15viii3.1933
C13···H112.642 (17)H8···H2v2.7294
C14···H163.2501H8···H3v2.5703
C14···H183.2552H8···H15viii3.1875
C14···H122.673 (17)H8···H13viii3.5949
C15···H193.2306H15···O2ix2.4604
C15···H132.622 (17)H15···N1iii3.2294
C16···H183.2430H15···C8iii3.2947
C17···H153.2058H15···C9iii3.3151
C17···H193.2044H15···C10iii3.2996
C18···H163.2425H15···C11iii3.3164
C19···H153.2315H15···H6x3.1225
C19···H133.300 (18)H15···H8iii3.1875
C19···H122.769 (18)H15···H11iii3.3154
H1···H22.3187H16···N1iii3.5481
H1···H112.3587H16···C6x3.2099
H2···H32.2795H16···C7x3.3756
H3···H52.4921H16···C11iii3.1354
H5···H62.2740H16···C12iii3.0046
H6···H72.3246H16···C13iii3.4816
H7···H82.2861H16···H2i3.3765
H15···H162.3051H16···H6x2.6995
H15···H132.4371H16···H7x3.0192
H18···H192.3055H16···H12iii3.1495
H19···H133.5569H16···H11iii3.4229
H19···H122.3008H18···C1iv3.5734
H13···H122.80 (3)H18···C2iv3.5731
H13···H112.44 (3)H18···C3iv3.4701
H12···H112.90 (3)H18···C4iv3.3461
O1···H1i3.2020H18···C9iv3.3321
O1···H5ii2.6614H18···C10iv3.4799
O1···H7x3.1257H18···C13v3.5298
O1···H19iii2.8387H18···H13v2.8315
O1···H11i3.219 (17)H18···H11v3.2054
O2···H5ii3.0276H19···O1viii2.8387
O2···H5iv3.4966H19···N1iv3.2127
O2···H6ii3.2431H19···C1v3.4374
O2···H15v2.4604H19···C10iv3.3466
O2···H13v3.375 (15)H19···H1v2.6192
O2···H11i3.269 (16)H19···H11v3.4503
N1···H1xi3.1668H13···O2ix3.375 (15)
N1···H2v3.3669H13···C4iii3.394 (17)
N1···H15viii3.2294H13···C5iii3.360 (17)
N1···H16viii3.5481H13···C6iii3.241 (16)
N1···H19iv3.2127H13···C7iii3.134 (17)
N1···H12iv3.013 (17)H13···C8iii3.148 (17)
N2···H1i3.5116H13···C9iii3.272 (16)
N2···H5ii3.1031H13···H7iii3.5723
N2···H11i3.530 (17)H13···H8iii3.5949
C1···H1xi3.0465H13···H18ix2.8315
C1···H18iv3.5734H12···N1iv3.013 (17)
C1···H19ix3.4374H12···C2v3.545 (16)
C2···H8ix3.3067H12···C11iv3.540 (17)
C2···H18iv3.5731H12···C12iv3.386 (17)
C2···H12ix3.545 (16)H12···H1v3.3760
C3···H8ix3.2321H12···H2v2.7617
C3···H18iv3.4701H12···H2xi3.1167
C4···H18iv3.3461H12···H16viii3.1495
C4···H13viii3.394 (17)H12···H12iv2.78 (3)
C5···H5xii3.4610H11···O1vi3.219 (17)
C5···H13viii3.360 (17)H11···O2vi3.269 (16)
C6···H7xiii3.2438H11···N2vi3.530 (17)
C6···H16xiv3.2099H11···H15viii3.3154
C6···H13viii3.241 (16)H11···H16viii3.4229
C7···H3v3.3298H11···H18ix3.2054
C7···H6xiii3.2526H11···H19ix3.4503
C7···H16xiv3.3756
C10—N1—C11119.53 (14)C17—C18—C19118.51 (15)
O1—N2—O2122.81 (17)C14—C19—C18121.37 (14)
O1—N2—C17118.37 (14)C2—C1—H1119.358
O2—N2—C17118.82 (15)C10—C1—H1119.366
C2—C1—C10121.28 (15)C1—C2—H2119.856
C1—C2—C3120.30 (15)C3—C2—H2119.847
C2—C3—C4120.87 (17)C2—C3—H3119.562
C3—C4—C5122.11 (17)C4—C3—H3119.566
C3—C4—C9119.53 (15)C4—C5—H5119.342
C5—C4—C9118.36 (15)C6—C5—H5119.342
C4—C5—C6121.32 (18)C5—C6—H6119.866
C5—C6—C7120.27 (16)C7—C6—H6119.866
C6—C7—C8120.49 (16)C6—C7—H7119.748
C7—C8—C9120.61 (16)C8—C7—H7119.758
C4—C9—C8118.94 (14)C7—C8—H8119.691
C4—C9—C10118.51 (13)C9—C8—H8119.700
C8—C9—C10122.54 (15)N1—C11—H11121.1 (10)
N1—C10—C1123.40 (13)C12—C11—H11117.4 (10)
N1—C10—C9116.99 (13)C11—C12—H12117.6 (11)
C1—C10—C9119.47 (15)C13—C12—H12118.8 (11)
N1—C11—C12121.48 (16)C12—C13—H13118.4 (10)
C11—C12—C13123.62 (16)C14—C13—H13115.6 (10)
C12—C13—C14126.01 (16)C14—C15—H15119.424
C13—C14—C15119.57 (14)C16—C15—H15119.428
C13—C14—C19122.30 (14)C15—C16—H16120.586
C15—C14—C19118.13 (15)C17—C16—H16120.584
C14—C15—C16121.15 (14)C17—C18—H18120.741
C15—C16—C17118.83 (14)C19—C18—H18120.752
N2—C17—C16118.69 (13)C14—C19—H19119.312
N2—C17—C18119.29 (14)C18—C19—H19119.319
C16—C17—C18122.01 (15)
C10—N1—C11—C12177.42 (12)C6—C7—C8—C90.2 (3)
C11—N1—C10—C141.0 (2)C7—C8—C9—C41.1 (2)
C11—N1—C10—C9143.39 (13)C7—C8—C9—C10179.35 (13)
O1—N2—C17—C160.2 (2)C4—C9—C10—N1178.53 (11)
O1—N2—C17—C18178.89 (13)C4—C9—C10—C12.72 (19)
O2—N2—C17—C16179.70 (13)C8—C9—C10—N11.1 (2)
O2—N2—C17—C180.6 (2)C8—C9—C10—C1176.87 (12)
C2—C1—C10—N1177.29 (13)N1—C11—C12—C13175.92 (14)
C2—C1—C10—C91.8 (3)C11—C12—C13—C14179.95 (14)
C10—C1—C2—C30.1 (3)C12—C13—C14—C15156.74 (15)
C1—C2—C3—C41.0 (3)C12—C13—C14—C1923.6 (3)
C2—C3—C4—C5179.08 (14)C13—C14—C15—C16179.30 (13)
C2—C3—C4—C90.0 (3)C13—C14—C19—C18179.44 (13)
C3—C4—C5—C6178.28 (14)C15—C14—C19—C180.9 (2)
C3—C4—C9—C8177.73 (12)C19—C14—C15—C161.1 (2)
C3—C4—C9—C101.9 (2)C14—C15—C16—C170.5 (3)
C5—C4—C9—C81.4 (2)C15—C16—C17—N2179.27 (12)
C5—C4—C9—C10179.04 (12)C15—C16—C17—C180.2 (3)
C9—C4—C5—C60.8 (3)N2—C17—C18—C19179.39 (12)
C4—C5—C6—C70.1 (3)C16—C17—C18—C190.3 (3)
C5—C6—C7—C80.4 (3)C17—C18—C19—C140.3 (3)
Symmetry codes: (i) x+1, y+3/2, z1/2; (ii) x+1, y, z1; (iii) x, y+3/2, z1/2; (iv) x+1, y+1, z+1; (v) x+1, y, z; (vi) x1, y+3/2, z+1/2; (vii) x1, y, z+1; (viii) x, y+3/2, z+1/2; (ix) x1, y, z; (x) x, y, z1; (xi) x, y+1, z+1; (xii) x, y+1, z+2; (xiii) x+1, y+1, z+2; (xiv) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O1vii0.932.663.422 (3)139
C15—H15···O2ix0.932.463.326 (3)155
Symmetry codes: (vii) x1, y, z+1; (ix) x1, y, z.

Experimental details

Crystal data
Chemical formulaC19H14N2O2
Mr302.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)7.7021 (5), 13.8713 (12), 14.2554 (10)
β (°) 98.096 (2)
V3)1507.8 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.20 × 0.10
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Rigaku, 1995)
Tmin, Tmax0.714, 0.991
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
14376, 3426, 1824
Rint0.038
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.125, 1.00
No. of reflections3426
No. of parameters220
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.16, 0.24

Computer programs: RAPID-AUTO (Rigaku, 2006), RAPID-AUTO (Rigaku, 1995), Il Milione (Burla et al., 2007), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.9302.6613.422 (3)139.0
C15—H15···O2ii0.9302.4603.326 (3)155.0
Symmetry codes: (i) x1, y, z+1; (ii) x1, y, z.
 

Acknowledgements

Fiancial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.

References

First citationBurla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609–613.  Web of Science CrossRef CAS IUCr Journals
First citationRigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
First citationRigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
First citationRigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
First citationRokade, Y. B. & Sayyed, R. Z. (2009). RASAYAN J. Chem. 2, 972–980.  CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationUpadhayaya, R. S., Vandavasi, J. K., Kardile, R. A., Lahore, S. V., Dixit, S. S., Deokar, H. S., Shinde, P. D., Sarmah, M. P. & Chattopadhyaya, J. (2010). Eur. J. Med. Chem. 2, 1854–1867.  Web of Science CrossRef
First citationYang, P., Ding, B. & Du, G.-X. (2012). Acta Cryst. E68, o2966.  CSD CrossRef IUCr Journals

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