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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Pages o2923-o2924
https://doi.org/10.1107/S1600536812038408

N′-[(E)-4-Hy­dr­oxy­benzyl­­idene]-2-(naph­tha­len-2-yl­­oxy)acetohydrazide

Rajni Kant,a* Vivek K. Gupta,a Kamini Kapoor,a S. Samshuddin,b B. Narayanab and B. K. Sarojinic

aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and cDepartment of Chemistry, P.A. College of Engineering, Nadupadavu, Mangalore 574 153, India
*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 31 August 2012; accepted 7 September 2012; online 12 September 2012)

The asymmetric unit of the title compound, C19H16N2O3, contains two independent mol­ecules in which the dihedral angles between the naphthalene ring system and the benzene ring are 10.0 (1) and 35.3 (1)°. In the crystal, mol­ecules are linked by N—H⋯O and O—H⋯O hydrogen bonds, forming a two-dimensional framework parallel to (001). Weak C—H⋯O and C—H⋯N hydrogen bonds complete a three-dimensional network.

Related literature

For the pharmacological importance of Schiff base hydrazones, see: Rollas & Kucukguzel (2007[Rollas, S. & Kucukguzel, S. G. (2007). Molecules, 12, 1910-1939.]). For related structures of Schiff base hydrazones, see: Fun et al. (2012a[Fun, H.-K., Loh, W.-S., Shetty, D. N., Narayana, B. & Sarojini, B. K. (2012a). Acta Cryst. E68, o2303-o2304.],b[Fun, H.-K., Quah, C. K., Shetty, D. N., Narayana, B. & Sarojini, B. K. (2012b). Acta Cryst. E68, o1484.]); Dutkiewicz et al. (2011[Dutkiewicz, G., Narayana, B., Samshuddin, S., Yathirajan, H. S. & Kubicki, M. (2011). J. Chem. Cryst. 41, 1442-1446.]); Narayana et al. (2007[Narayana, B., Sunil, K., Yathirajan, H. S., Sarojini, B. K. & Bolte, M. (2007). Acta Cryst. E63, o2948.]), Sarojini et al. (2007a[Sarojini, B. K., Narayana, B., Sunil, K., Yathirajan, H. S. & Bolte, M. (2007a). Acta Cryst. E63, o3862-o3863.],b[Sarojini, B. K., Narayana, B., Sunil, K., Yathirajan, H. S. & Bolte, M. (2007b). Acta Cryst. E63, o3551.],c[Sarojini, B. K., Yathirajan, H. S., Sunil, K., Narayana, B. & Bolte, M. (2007c). Acta Cryst. E63, o3487.]); Yathirajan et al. (2007a[Yathirajan, H. S., Sarojini, B. K., Narayana, B., Sunil, K. & Bolte, M. (2007a). Acta Cryst. E63, o2719.],b[Yathirajan, H. S., Narayana, B., Sunil, K., Sarojini, B. K. & Bolte, M. (2007b). Acta Cryst. E63, o2565.]); Huang (2009[Huang, H.-T. (2009). Acta Cryst. E65, o892.]).

[Scheme 1]

Experimental

Crystal data

  • C19H16N2O3

  • Mr = 320.34

  • Orthorhombic, P c a 21

  • a = 17.2908 (8) Å

  • b = 6.9946 (3) Å

  • c = 27.1617 (11) Å

  • V = 3285.0 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.3 × 0.2 × 0.2 mm
Data collection

  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.899, Tmax = 1.000

  • 19652 measured reflections

  • 3632 independent reflections

  • 2583 reflections with I > 2σ(I)

  • Rint = 0.042
Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.112

  • S = 1.07

  • 3632 reflections

  • 449 parameters

  • 5 restraints

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

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.14 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O7A—H7A⋯O11Bi 0.82 (3) 1.89 (4) 2.613 (5) 145 (5)
O7B—H7B⋯O11Aii 0.83 (4) 1.82 (4) 2.642 (4) 170 (4)
N10B—H10B⋯O7Aiii 0.87 (2) 2.25 (2) 3.036 (5) 151 (1)
C3B—H3B⋯N9Aii 0.93 2.46 3.368 (6) 166
C12A—H12B⋯O11Biv 0.97 2.58 3.463 (5) 151
C22A—H22A⋯O11Biv 0.93 2.60 3.391 (5) 144
C22B—H22B⋯O11Av 0.93 2.56 3.390 (5) 149
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+1, z]; (ii) x, y-1, z; (iii) [x+{\script{1\over 2}}, -y, z]; (iv) [-x+1, -y+1, z+{\script{1\over 2}}]; (v) [-x+1, -y+1, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536812038408/lh5528sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038408/lh5528Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812038408/lh5528Isup3.cml

checkCIF report


Comment top

The pharmacological importance of Schiff base hydrazones are well documented (Rollas & Kucukguzel, 2007). The crystal structure of some Schiff base hydrazones viz. N-[(E)-4-chlorobenzylidene]pyridine-4-carbohydrazide monohydrate (Fun et al.,2012a),N'-(2,6-difluorobenzylidene) pyridine-4-carbohydrazide (Fun et al.,2012b),two new Schiff base hydrazones derived from biphenyl-4-carbohydrazide (Dutkiewicz et al., 2011),2-bromo-N'-[(E)-(4-fluorophenyl)methylene]-5-methoxybenzohydrazide monohydrate (Narayana et al.,2007),2-bromo-N'-[(E)-4-hydroxybenzylidene] -5-methoxybenzohydrazide (Sarojini et al.,2007a),N'-isopropylidene- 6-methoxy-2-naphthohydrazide (Sarojini et al.,2007b), 2-bromo-N'-iso propylidene-5-methoxybenzohydrazide (Sarojini et al.,2007c), 2-bromo-5-methoxy-N'-[(E)-(2-nitrophenyl)methylene]benzohydrazide (Yathirajan et al., 2007a)and N'-[(1E)-(4-fluorophenyl)methylene] -6-methoxy-2-naphthohydrazide (Yathirajan et al., 2007b) have been reported. In view of the importance of Schiff base hydrazones, the title compound (I) is prepared and its crystal structure is reported.

The asymmetric unit of the title compound comprises of two crystallographically independent molecules, A and B (Fig. 1). The geometry of both independent molecules indicates a high degree of similarity in terms of their bond distances and bond angles and are comparable with a similar crystal structure (Huang, 2009). The dihedral angle between naphthalene ring system and benzene benzene ring is 10.0 (1)° in molecule A and 35.3 (1)° in molecule B. In the crystal, molecules are connected via O—H···O, N—H···O, weak C—H···O and weak C—H···N hydrogen bonds into a three-dimensional supramolecular structure.

Related literature top

For the pharmacological importance of Schiff base hydrazones, see: Rollas & Kucukguzel (2007). For related structures of Schiff base hydrazones, see: Fun et al. (2012a,b); Dutkiewicz et al. (2011); Narayana et al. (2007), Sarojini et al. (2007a,b,c); Yathirajan et al. (2007a,b); Huang (2009).

Experimental top

A mixture of 2-(naphthalen-2-yloxy)acetohydrazide (0.216 g, 0.001 mol) and 4-hydroxybenzaldehyde (0.122 g, 0.001 mol) in 30 ml ethanol containing 2 drops of concentrated sulfuric acid was refluxed for about 3 h. On cooling solid was separated which was filtered and recrystallized from ethanol. The yield was 82%. (m.p. 436 K). The single-crystal was grown from a solution of the title compound in DMF by the slow evaporation method.

Refinement top

The N and O-bound H atoms were located in a difference Fourier map and refined independently with the constraints N—H = 0.86 (1) and O—H = 0.82 (1) Å. All other H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.97 Å and with Uiso(H) = 1.2Ueq(C). In the absence of significant anomalous dispersion effects the Friedel pairs were merged.

Structure description top

The pharmacological importance of Schiff base hydrazones are well documented (Rollas & Kucukguzel, 2007). The crystal structure of some Schiff base hydrazones viz. N-[(E)-4-chlorobenzylidene]pyridine-4-carbohydrazide monohydrate (Fun et al.,2012a),N'-(2,6-difluorobenzylidene) pyridine-4-carbohydrazide (Fun et al.,2012b),two new Schiff base hydrazones derived from biphenyl-4-carbohydrazide (Dutkiewicz et al., 2011),2-bromo-N'-[(E)-(4-fluorophenyl)methylene]-5-methoxybenzohydrazide monohydrate (Narayana et al.,2007),2-bromo-N'-[(E)-4-hydroxybenzylidene] -5-methoxybenzohydrazide (Sarojini et al.,2007a),N'-isopropylidene- 6-methoxy-2-naphthohydrazide (Sarojini et al.,2007b), 2-bromo-N'-iso propylidene-5-methoxybenzohydrazide (Sarojini et al.,2007c), 2-bromo-5-methoxy-N'-[(E)-(2-nitrophenyl)methylene]benzohydrazide (Yathirajan et al., 2007a)and N'-[(1E)-(4-fluorophenyl)methylene] -6-methoxy-2-naphthohydrazide (Yathirajan et al., 2007b) have been reported. In view of the importance of Schiff base hydrazones, the title compound (I) is prepared and its crystal structure is reported.

The asymmetric unit of the title compound comprises of two crystallographically independent molecules, A and B (Fig. 1). The geometry of both independent molecules indicates a high degree of similarity in terms of their bond distances and bond angles and are comparable with a similar crystal structure (Huang, 2009). The dihedral angle between naphthalene ring system and benzene benzene ring is 10.0 (1)° in molecule A and 35.3 (1)° in molecule B. In the crystal, molecules are connected via O—H···O, N—H···O, weak C—H···O and weak C—H···N hydrogen bonds into a three-dimensional supramolecular structure.

For the pharmacological importance of Schiff base hydrazones, see: Rollas & Kucukguzel (2007). For related structures of Schiff base hydrazones, see: Fun et al. (2012a,b); Dutkiewicz et al. (2011); Narayana et al. (2007), Sarojini et al. (2007a,b,c); Yathirajan et al. (2007a,b); Huang (2009).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. ORTEP-3 view (Farrugia, 1997) of the asymmetric unit. The ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A molecular packing view of the title compound along the b axis, showing hydrogen bonds (dashed lines). For clarity, hydrogen atoms which are not involved in hydrogen bonding have been omitted.
N'-[(E)-4-Hydroxybenzylidene]-2-(naphthalen-2-yloxy)acetohydrazide top
Crystal data top
C19H16N2O3F(000) = 1344
Mr = 320.34Dx = 1.295 Mg m−3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 6059 reflections
a = 17.2908 (8) Åθ = 3.5–29.0°
b = 6.9946 (3) ŵ = 0.09 mm−1
c = 27.1617 (11) ÅT = 293 K
V = 3285.0 (2) Å3Block, white
Z = 80.3 × 0.2 × 0.2 mm
Data collection top
Oxford Diffraction Xcalibur Sapphire3
diffractometer		3632 independent reflections
Radiation source: fine-focus sealed tube2583 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
Detector resolution: 16.1049 pixels mm-1θmax = 27.0°, θmin = 3.5°
ω scansh = −21→21
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		k = −8→8
Tmin = 0.899, Tmax = 1.000l = −34→30
19652 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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0343P)2 + 1.0102P]
where P = (Fo2 + 2Fc2)/3
3632 reflections(Δ/σ)max = 0.001
449 parametersΔρmax = 0.15 e Å−3
5 restraintsΔρmin = −0.14 e Å−3
Crystal data top
C19H16N2O3V = 3285.0 (2) Å3
Mr = 320.34Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 17.2908 (8) ŵ = 0.09 mm−1
b = 6.9946 (3) ÅT = 293 K
c = 27.1617 (11) Å0.3 × 0.2 × 0.2 mm
Data collection top
Oxford Diffraction Xcalibur Sapphire3
diffractometer		3632 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		2583 reflections with I > 2σ(I)
Tmin = 0.899, Tmax = 1.000Rint = 0.042
19652 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0495 restraints
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.15 e Å−3
3632 reflectionsΔρmin = −0.14 e Å−3
449 parameters
Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C1A0.2482 (2)0.4059 (6)−0.14893 (15)0.0502 (10)
C2A0.2422 (3)0.2457 (7)−0.17829 (19)0.0699 (13)
H2A0.26340.1307−0.16760.084*
C3A0.2052 (3)0.2536 (7)−0.22309 (19)0.0743 (14)
H3A0.20220.1451−0.24280.089*
C4A0.1728 (2)0.4225 (6)−0.23867 (17)0.0546 (11)
C6A0.2168 (2)0.5745 (6)−0.16513 (15)0.0546 (10)
H6A0.22100.6841−0.14590.066*
C5A0.1786 (2)0.5827 (6)−0.21025 (16)0.0532 (10)
H5A0.15710.6972−0.22100.064*
O7A0.1354 (2)0.4179 (5)−0.28308 (13)0.0770 (10)
C8A0.2889 (2)0.3847 (6)−0.10197 (15)0.0513 (10)
H8A0.30090.2622−0.09110.062*
N9A0.3085 (2)0.5267 (5)−0.07535 (14)0.0510 (9)
N10A0.3504 (2)0.4753 (5)−0.03367 (13)0.0447 (8)
C11A0.3730 (2)0.6093 (6)−0.00186 (14)0.0459 (9)
O11A0.35586 (19)0.7796 (4)−0.00537 (11)0.0636 (8)
O12A0.44014 (15)0.3498 (4)0.03806 (10)0.0495 (7)
C12A0.4206 (2)0.5452 (5)0.04084 (16)0.0480 (9)
H12A0.46770.62050.04210.058*
H12B0.39220.56820.07100.058*
C13A0.4888 (2)0.2836 (6)0.07439 (14)0.0442 (9)
C14A0.5162 (2)0.0966 (6)0.06702 (16)0.0535 (10)
H14A0.50110.02710.03950.064*
C15A0.5655 (3)0.0182 (6)0.1010 (2)0.0632 (14)
H15A0.5823−0.10710.09690.076*
C16A0.5912 (2)0.1234 (7)0.14197 (16)0.0582 (11)
C17A0.6445 (3)0.0489 (9)0.1769 (2)0.0816 (17)
H17A0.6626−0.07570.17380.098*
C18A0.6692 (3)0.1605 (11)0.2151 (2)0.0922 (18)
H18A0.70430.11040.23760.111*
C19A0.6430 (3)0.3479 (10)0.2214 (2)0.0865 (16)
H19A0.66090.42150.24750.104*
C20A0.5910 (3)0.4217 (8)0.18875 (17)0.0684 (13)
H20A0.57320.54620.19290.082*
C21A0.5638 (2)0.3105 (6)0.14854 (14)0.0518 (10)
C22A0.5118 (2)0.3884 (6)0.11403 (14)0.0496 (9)
H22A0.49310.51190.11830.059*
C1B0.4922 (2)−0.0263 (6)−0.19756 (15)0.0502 (11)
C2B0.4561 (3)−0.1702 (6)−0.17164 (15)0.0601 (11)
H2B0.4522−0.2908−0.18580.072*
C3B0.4257 (3)−0.1410 (6)−0.12522 (16)0.0562 (11)
H3B0.4010−0.2401−0.10870.067*
C4B0.4324 (2)0.0357 (6)−0.10368 (17)0.0523 (11)
C5B0.4652 (3)0.1827 (6)−0.12975 (18)0.0682 (13)
H5B0.46760.3041−0.11590.082*
C6B0.4949 (3)0.1526 (6)−0.17646 (18)0.0640 (12)
H6B0.51670.2539−0.19370.077*
O7B0.4058 (2)0.0738 (5)−0.05744 (12)0.0690 (9)
C8B0.5265 (2)−0.0703 (6)−0.24509 (15)0.0530 (10)
H8B0.5228−0.1939−0.25750.064*
N9B0.56127 (19)0.0566 (5)−0.26994 (13)0.0487 (8)
N10B0.5977 (2)−0.0100 (5)−0.31289 (13)0.0468 (9)
C11B0.6254 (2)0.1164 (6)−0.34475 (14)0.0440 (9)
C12B0.6703 (2)0.0412 (5)−0.38801 (15)0.0458 (9)
H12C0.64030.0597−0.41780.055*
H12D0.71790.1134−0.39130.055*
C13B0.7364 (2)−0.2279 (5)−0.41863 (14)0.0428 (9)
O11B0.61664 (19)0.2887 (4)−0.34142 (11)0.0640 (8)
O12B0.68813 (15)−0.1539 (3)−0.38294 (9)0.0482 (6)
C14B0.7616 (2)−0.4145 (6)−0.41022 (15)0.0513 (10)
H14B0.7457−0.4797−0.38220.062*
C15B0.8093 (3)−0.5007 (6)−0.44298 (19)0.0552 (12)
H15B0.8250−0.6261−0.43740.066*
C16B0.8360 (2)−0.4036 (6)−0.48580 (16)0.0530 (10)
C17B0.8876 (3)−0.4868 (9)−0.5205 (2)0.0770 (17)
H17B0.9044−0.6120−0.51630.092*
C18B0.9122 (3)−0.3839 (10)−0.5597 (2)0.0901 (18)
H18B0.9465−0.4389−0.58190.108*
C19B0.8870 (3)−0.1978 (9)−0.5674 (2)0.0816 (16)
H19B0.9039−0.1302−0.59480.098*
C20B0.8381 (3)−0.1149 (7)−0.53511 (17)0.0649 (12)
H20B0.82190.0102−0.54050.078*
C21B0.8109 (2)−0.2146 (6)−0.49328 (14)0.0492 (9)
C22B0.7597 (2)−0.1282 (5)−0.45945 (15)0.0451 (9)
H22B0.7419−0.0045−0.46480.054*
H10A0.3612 (19)0.3556 (19)−0.0309 (14)0.035 (10)*
H10B0.609 (2)−0.131 (2)−0.3160 (16)0.052 (12)*
H7B0.394 (3)−0.026 (5)−0.043 (2)0.10 (2)*
H7A0.126 (3)0.530 (3)−0.290 (2)0.12 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.046 (2)0.057 (3)0.047 (3)−0.0035 (19)−0.0026 (18)0.002 (2)
C2A0.082 (3)0.056 (3)0.071 (3)0.006 (2)−0.033 (3)−0.001 (2)
C3A0.100 (4)0.055 (3)0.068 (3)0.005 (2)−0.033 (3)−0.006 (2)
C4A0.062 (3)0.054 (2)0.048 (3)−0.010 (2)−0.014 (2)0.004 (2)
C6A0.063 (3)0.057 (2)0.043 (3)0.003 (2)0.002 (2)−0.003 (2)
C5A0.056 (2)0.054 (2)0.050 (3)0.0053 (19)−0.0005 (19)0.011 (2)
O7A0.109 (3)0.060 (2)0.061 (2)−0.0103 (19)−0.036 (2)0.0106 (18)
C8A0.053 (2)0.057 (2)0.044 (2)−0.0005 (19)−0.0018 (18)0.006 (2)
N9A0.057 (2)0.058 (2)0.038 (2)−0.0010 (16)0.0012 (16)0.0027 (17)
N10A0.054 (2)0.045 (2)0.035 (2)0.0009 (15)−0.0021 (16)0.0023 (16)
C11A0.057 (2)0.049 (2)0.032 (2)0.0011 (18)0.0111 (17)0.0004 (19)
O11A0.101 (2)0.0446 (16)0.0455 (17)0.0172 (15)0.0071 (16)−0.0022 (14)
O12A0.0599 (16)0.0472 (15)0.0413 (15)0.0050 (12)−0.0073 (13)−0.0036 (13)
C12A0.058 (2)0.050 (2)0.036 (2)−0.0013 (18)0.0018 (19)−0.0048 (19)
C13A0.043 (2)0.055 (2)0.035 (2)0.0013 (17)0.0010 (16)0.0016 (18)
C14A0.056 (2)0.057 (3)0.047 (3)0.002 (2)0.006 (2)−0.002 (2)
C15A0.058 (3)0.061 (3)0.071 (4)0.015 (2)0.014 (3)0.012 (3)
C16A0.042 (2)0.085 (3)0.047 (3)0.004 (2)0.0051 (19)0.014 (2)
C17A0.057 (3)0.112 (4)0.076 (4)0.018 (3)0.005 (3)0.028 (3)
C18A0.060 (3)0.158 (6)0.059 (4)0.009 (4)−0.016 (3)0.025 (4)
C19A0.061 (3)0.130 (5)0.069 (3)−0.011 (3)−0.013 (3)0.005 (4)
C20A0.061 (3)0.096 (4)0.049 (3)−0.012 (2)−0.007 (2)0.007 (3)
C21A0.043 (2)0.073 (3)0.039 (2)−0.0045 (19)0.0028 (17)0.005 (2)
C22A0.050 (2)0.058 (2)0.040 (2)−0.0047 (17)0.0019 (18)0.0021 (19)
C1B0.048 (2)0.056 (3)0.046 (3)−0.0055 (18)0.0061 (18)−0.008 (2)
C2B0.080 (3)0.053 (3)0.047 (3)−0.014 (2)0.001 (2)−0.012 (2)
C3B0.074 (3)0.052 (2)0.042 (2)−0.008 (2)0.004 (2)0.000 (2)
C4B0.056 (2)0.058 (3)0.043 (2)0.0069 (19)0.008 (2)0.000 (2)
C5B0.087 (3)0.055 (3)0.063 (3)−0.007 (2)0.023 (3)−0.016 (2)
C6B0.075 (3)0.052 (3)0.065 (3)−0.010 (2)0.026 (2)−0.007 (2)
O7B0.098 (3)0.057 (2)0.052 (2)0.0083 (18)0.0201 (17)−0.0010 (17)
C8B0.057 (2)0.057 (2)0.045 (2)−0.0069 (19)0.0052 (19)−0.010 (2)
N9B0.0492 (19)0.057 (2)0.040 (2)−0.0007 (16)0.0070 (16)−0.0064 (16)
N10B0.055 (2)0.047 (2)0.038 (2)0.0013 (15)0.0037 (16)−0.0056 (16)
C11B0.053 (2)0.046 (2)0.033 (2)0.0033 (17)−0.0060 (17)−0.0015 (18)
C12B0.054 (2)0.049 (2)0.034 (2)−0.0003 (17)0.0010 (19)0.0036 (18)
C13B0.043 (2)0.050 (2)0.036 (2)−0.0021 (17)−0.0034 (15)−0.0031 (18)
O11B0.107 (2)0.0440 (16)0.0407 (17)0.0083 (15)0.0065 (16)0.0015 (13)
O12B0.0604 (17)0.0442 (15)0.0400 (15)0.0033 (12)0.0093 (12)0.0018 (13)
C14B0.054 (2)0.055 (2)0.045 (3)0.0036 (19)−0.0071 (19)0.0054 (19)
C15B0.055 (3)0.053 (3)0.057 (3)0.0107 (19)−0.013 (2)−0.004 (2)
C16B0.039 (2)0.069 (3)0.051 (3)0.0026 (18)−0.0093 (18)−0.011 (2)
C17B0.051 (3)0.108 (4)0.072 (4)0.021 (3)−0.004 (3)−0.025 (3)
C18B0.058 (3)0.142 (5)0.071 (4)0.010 (3)0.019 (3)−0.028 (4)
C19B0.064 (3)0.117 (5)0.064 (3)−0.010 (3)0.020 (3)−0.005 (3)
C20B0.061 (3)0.080 (3)0.054 (3)−0.011 (2)0.008 (2)0.000 (2)
C21B0.042 (2)0.065 (3)0.041 (2)−0.0069 (18)−0.0033 (17)−0.0069 (19)
C22B0.045 (2)0.048 (2)0.042 (2)−0.0014 (17)−0.0002 (17)−0.0015 (19)
Geometric parameters (Å, º) top
C1A—C6A1.371 (6)C1B—C2B1.377 (6)
C1A—C2A1.380 (6)C1B—C6B1.377 (6)
C1A—C8A1.464 (5)C1B—C8B1.454 (6)
C2A—C3A1.375 (6)C2B—C3B1.382 (6)
C2A—H2A0.9300C2B—H2B0.9300
C3A—C4A1.375 (6)C3B—C4B1.372 (6)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.364 (6)C4B—O7B1.364 (5)
C4A—O7A1.369 (5)C4B—C5B1.372 (6)
C6A—C5A1.393 (6)C5B—C6B1.385 (6)
C6A—H6A0.9300C5B—H5B0.9300
C5A—H5A0.9300C6B—H6B0.9300
O7A—H7A0.825 (11)O7B—H7B0.826 (11)
C8A—N9A1.275 (5)C8B—N9B1.267 (5)
C8A—H8A0.9300C8B—H8B0.9300
N9A—N10A1.391 (5)N9B—N10B1.405 (5)
N10A—C11A1.333 (5)N10B—C11B1.327 (5)
N10A—H10A0.861 (10)N10B—H10B0.868 (10)
C11A—O11A1.231 (4)C11B—O11B1.218 (4)
C11A—C12A1.492 (6)C11B—C12B1.504 (5)
O12A—C13A1.377 (4)C12B—O12B1.405 (4)
O12A—C12A1.410 (4)C12B—H12C0.9700
C12A—H12A0.9700C12B—H12D0.9700
C12A—H12B0.9700C13B—C22B1.370 (5)
C13A—C22A1.362 (5)C13B—O12B1.380 (4)
C13A—C14A1.405 (6)C13B—C14B1.395 (5)
C14A—C15A1.371 (7)C14B—C15B1.355 (6)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.406 (7)C15B—C16B1.424 (7)
C15A—H15A0.9300C15B—H15B0.9300
C16A—C21A1.403 (6)C16B—C21B1.406 (6)
C16A—C17A1.423 (7)C16B—C17B1.422 (6)
C17A—C18A1.366 (8)C17B—C18B1.353 (8)
C17A—H17A0.9300C17B—H17B0.9300
C18A—C19A1.397 (8)C18B—C19B1.388 (8)
C18A—H18A0.9300C18B—H18B0.9300
C19A—C20A1.364 (7)C19B—C20B1.349 (7)
C19A—H19A0.9300C19B—H19B0.9300
C20A—C21A1.421 (6)C20B—C21B1.413 (6)
C20A—H20A0.9300C20B—H20B0.9300
C21A—C22A1.409 (5)C21B—C22B1.412 (5)
C22A—H22A0.9300C22B—H22B0.9300
C6A—C1A—C2A118.9 (4)C2B—C1B—C6B117.8 (4)
C6A—C1A—C8A123.9 (4)C2B—C1B—C8B118.9 (4)
C2A—C1A—C8A117.2 (4)C6B—C1B—C8B123.2 (4)
C3A—C2A—C1A120.9 (4)C1B—C2B—C3B122.1 (4)
C3A—C2A—H2A119.5C1B—C2B—H2B119.0
C1A—C2A—H2A119.5C3B—C2B—H2B119.0
C2A—C3A—C4A119.8 (4)C4B—C3B—C2B119.4 (4)
C2A—C3A—H3A120.1C4B—C3B—H3B120.3
C4A—C3A—H3A120.1C2B—C3B—H3B120.3
C5A—C4A—O7A123.6 (4)O7B—C4B—C5B117.9 (4)
C5A—C4A—C3A120.1 (4)O7B—C4B—C3B122.7 (4)
O7A—C4A—C3A116.3 (4)C5B—C4B—C3B119.3 (4)
C1A—C6A—C5A120.3 (4)C4B—C5B—C6B120.8 (4)
C1A—C6A—H6A119.8C4B—C5B—H5B119.6
C5A—C6A—H6A119.8C6B—C5B—H5B119.6
C4A—C5A—C6A119.9 (4)C1B—C6B—C5B120.5 (4)
C4A—C5A—H5A120.0C1B—C6B—H6B119.8
C6A—C5A—H5A120.0C5B—C6B—H6B119.8
C4A—O7A—H7A107 (4)C4B—O7B—H7B110 (4)
N9A—C8A—C1A122.9 (4)N9B—C8B—C1B121.2 (4)
N9A—C8A—H8A118.6N9B—C8B—H8B119.4
C1A—C8A—H8A118.6C1B—C8B—H8B119.4
C8A—N9A—N10A113.5 (3)C8B—N9B—N10B115.0 (3)
C11A—N10A—N9A119.9 (3)C11B—N10B—N9B118.8 (3)
C11A—N10A—H10A124 (3)C11B—N10B—H10B120 (3)
N9A—N10A—H10A116 (3)N9B—N10B—H10B120 (3)
O11A—C11A—N10A124.0 (4)O11B—C11B—N10B124.5 (4)
O11A—C11A—C12A118.9 (4)O11B—C11B—C12B117.9 (4)
N10A—C11A—C12A117.0 (4)N10B—C11B—C12B117.6 (3)
C13A—O12A—C12A115.7 (3)O12B—C12B—C11B112.1 (3)
O12A—C12A—C11A112.4 (3)O12B—C12B—H12C109.2
O12A—C12A—H12A109.1C11B—C12B—H12C109.2
C11A—C12A—H12A109.1O12B—C12B—H12D109.2
O12A—C12A—H12B109.1C11B—C12B—H12D109.2
C11A—C12A—H12B109.1H12C—C12B—H12D107.9
H12A—C12A—H12B107.8C22B—C13B—O12B123.7 (3)
C22A—C13A—O12A124.3 (3)C22B—C13B—C14B121.1 (4)
C22A—C13A—C14A121.0 (4)O12B—C13B—C14B115.2 (3)
O12A—C13A—C14A114.6 (3)C13B—O12B—C12B115.3 (3)
C15A—C14A—C13A119.1 (4)C15B—C14B—C13B120.0 (4)
C15A—C14A—H14A120.5C15B—C14B—H14B120.0
C13A—C14A—H14A120.5C13B—C14B—H14B120.0
C14A—C15A—C16A121.3 (4)C14B—C15B—C16B121.4 (4)
C14A—C15A—H15A119.3C14B—C15B—H15B119.3
C16A—C15A—H15A119.3C16B—C15B—H15B119.3
C21A—C16A—C15A118.8 (4)C21B—C16B—C17B118.9 (5)
C21A—C16A—C17A118.4 (5)C21B—C16B—C15B117.8 (4)
C15A—C16A—C17A122.8 (5)C17B—C16B—C15B123.3 (4)
C18A—C17A—C16A120.0 (5)C18B—C17B—C16B120.0 (5)
C18A—C17A—H17A120.0C18B—C17B—H17B120.0
C16A—C17A—H17A120.0C16B—C17B—H17B120.0
C17A—C18A—C19A121.8 (5)C17B—C18B—C19B121.2 (5)
C17A—C18A—H18A119.1C17B—C18B—H18B119.4
C19A—C18A—H18A119.1C19B—C18B—H18B119.4
C20A—C19A—C18A119.3 (5)C20B—C19B—C18B120.1 (5)
C20A—C19A—H19A120.3C20B—C19B—H19B119.9
C18A—C19A—H19A120.3C18B—C19B—H19B119.9
C19A—C20A—C21A120.7 (5)C19B—C20B—C21B121.2 (5)
C19A—C20A—H20A119.7C19B—C20B—H20B119.4
C21A—C20A—H20A119.7C21B—C20B—H20B119.4
C16A—C21A—C22A119.4 (4)C16B—C21B—C22B120.1 (4)
C16A—C21A—C20A119.8 (4)C16B—C21B—C20B118.5 (4)
C22A—C21A—C20A120.7 (4)C22B—C21B—C20B121.4 (4)
C13A—C22A—C21A120.3 (4)C13B—C22B—C21B119.6 (3)
C13A—C22A—H22A119.9C13B—C22B—H22B120.2
C21A—C22A—H22A119.9C21B—C22B—H22B120.2
C6A—C1A—C2A—C3A−0.1 (8)C6B—C1B—C2B—C3B−2.3 (7)
C8A—C1A—C2A—C3A−179.7 (5)C8B—C1B—C2B—C3B176.7 (4)
C1A—C2A—C3A—C4A−1.0 (8)C1B—C2B—C3B—C4B−1.0 (7)
C2A—C3A—C4A—C5A1.3 (8)C2B—C3B—C4B—O7B−178.0 (4)
C2A—C3A—C4A—O7A−178.4 (5)C2B—C3B—C4B—C5B3.6 (7)
C2A—C1A—C6A—C5A0.8 (6)O7B—C4B—C5B—C6B178.5 (4)
C8A—C1A—C6A—C5A−179.7 (4)C3B—C4B—C5B—C6B−3.0 (7)
O7A—C4A—C5A—C6A179.1 (4)C2B—C1B—C6B—C5B2.9 (7)
C3A—C4A—C5A—C6A−0.6 (7)C8B—C1B—C6B—C5B−176.1 (4)
C1A—C6A—C5A—C4A−0.4 (6)C4B—C5B—C6B—C1B−0.3 (7)
C6A—C1A—C8A—N9A−10.6 (6)C2B—C1B—C8B—N9B−178.9 (4)
C2A—C1A—C8A—N9A169.0 (4)C6B—C1B—C8B—N9B0.0 (7)
C1A—C8A—N9A—N10A−176.5 (3)C1B—C8B—N9B—N10B174.3 (4)
C8A—N9A—N10A—C11A−178.3 (4)C8B—N9B—N10B—C11B170.0 (4)
N9A—N10A—C11A—O11A3.8 (6)N9B—N10B—C11B—O11B−5.7 (6)
N9A—N10A—C11A—C12A−177.4 (3)N9B—N10B—C11B—C12B174.6 (3)
C13A—O12A—C12A—C11A175.5 (3)O11B—C11B—C12B—O12B169.2 (3)
O11A—C11A—C12A—O12A−175.8 (3)N10B—C11B—C12B—O12B−11.0 (5)
N10A—C11A—C12A—O12A5.3 (5)C22B—C13B—O12B—C12B−6.8 (5)
C12A—O12A—C13A—C22A6.7 (5)C14B—C13B—O12B—C12B172.4 (3)
C12A—O12A—C13A—C14A−171.3 (3)C11B—C12B—O12B—C13B−173.3 (3)
C22A—C13A—C14A—C15A1.4 (6)C22B—C13B—C14B—C15B−0.7 (6)
O12A—C13A—C14A—C15A179.6 (4)O12B—C13B—C14B—C15B−179.9 (4)
C13A—C14A—C15A—C16A−2.3 (6)C13B—C14B—C15B—C16B1.3 (6)
C14A—C15A—C16A—C21A1.7 (6)C14B—C15B—C16B—C21B−0.3 (6)
C14A—C15A—C16A—C17A−177.6 (4)C14B—C15B—C16B—C17B178.4 (4)
C21A—C16A—C17A—C18A−1.4 (7)C21B—C16B—C17B—C18B0.5 (7)
C15A—C16A—C17A—C18A177.9 (5)C15B—C16B—C17B—C18B−178.2 (5)
C16A—C17A—C18A—C19A0.5 (8)C16B—C17B—C18B—C19B−1.1 (8)
C17A—C18A—C19A—C20A0.5 (9)C17B—C18B—C19B—C20B1.1 (9)
C18A—C19A—C20A—C21A−0.4 (8)C18B—C19B—C20B—C21B−0.5 (8)
C15A—C16A—C21A—C22A−0.3 (6)C17B—C16B—C21B—C22B−180.0 (4)
C17A—C16A—C21A—C22A179.1 (4)C15B—C16B—C21B—C22B−1.2 (5)
C15A—C16A—C21A—C20A−177.9 (4)C17B—C16B—C21B—C20B0.0 (6)
C17A—C16A—C21A—C20A1.5 (6)C15B—C16B—C21B—C20B178.8 (4)
C19A—C20A—C21A—C16A−0.6 (6)C19B—C20B—C21B—C16B0.0 (6)
C19A—C20A—C21A—C22A−178.2 (4)C19B—C20B—C21B—C22B180.0 (4)
O12A—C13A—C22A—C21A−177.9 (3)O12B—C13B—C22B—C21B178.3 (3)
C14A—C13A—C22A—C21A0.0 (6)C14B—C13B—C22B—C21B−0.9 (5)
C16A—C21A—C22A—C13A−0.6 (6)C16B—C21B—C22B—C13B1.8 (5)
C20A—C21A—C22A—C13A177.0 (4)C20B—C21B—C22B—C13B−178.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7A—H7A···O11Bi0.82 (3)1.89 (4)2.613 (5)145 (5)
O7B—H7B···O11Aii0.83 (4)1.82 (4)2.642 (4)170 (4)
N10B—H10B···O7Aiii0.87 (2)2.25 (2)3.036 (5)151 (1)
C3B—H3B···N9Aii0.932.463.368 (6)166
C12A—H12B···O11Biv0.972.583.463 (5)151
C22A—H22A···O11Biv0.932.603.391 (5)144
C22B—H22B···O11Av0.932.563.390 (5)149
Symmetry codes: (i) x−1/2, −y+1, z; (ii) x, y−1, z; (iii) x+1/2, −y, z; (iv) −x+1, −y+1, z+1/2; (v) −x+1, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formulaC19H16N2O3
Mr320.34
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)293
a, b, c (Å)17.2908 (8), 6.9946 (3), 27.1617 (11)
V (Å3)3285.0 (2)
Z8
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.3 × 0.2 × 0.2
Data collection
DiffractometerOxford Diffraction Xcalibur Sapphire3
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.899, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		19652, 3632, 2583
Rint0.042
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.112, 1.07
No. of reflections3632
No. of parameters449
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.15, −0.14

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7A—H7A···O11Bi0.82 (3)1.89 (4)2.613 (5)145 (5)
O7B—H7B···O11Aii0.83 (4)1.82 (4)2.642 (4)170 (4)
N10B—H10B···O7Aiii0.87 (2)2.25 (2)3.036 (5)151 (1)
C3B—H3B···N9Aii0.932.463.368 (6)166
C12A—H12B···O11Biv0.972.583.463 (5)151
C22A—H22A···O11Biv0.932.603.391 (5)144
C22B—H22B···O11Av0.932.563.390 (5)149
Symmetry codes: (i) x−1/2, −y+1, z; (ii) x, y−1, z; (iii) x+1/2, −y, z; (iv) −x+1, −y+1, z+1/2; (v) −x+1, −y+1, z−1/2.
 

Acknowledgements

RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. BN thanks the UGC for financial assistance through the BSR one-time grant for the purchase of chemicals. SS thanks Mangalore University for the research facilities.

References

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 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFun, H.-K., Loh, W.-S., Shetty, D. N., Narayana, B. & Sarojini, B. K. (2012a). Acta Cryst. E68, o2303–o2304.  CSD CrossRef IUCr Journals Google Scholar
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ISSN: 2056-9890
Volume 68| Part 10| October 2012| Pages o2923-o2924
https://doi.org/10.1107/S1600536812038408
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