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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 71| Part 12| December 2015| Pages o941-o942
https://doi.org/10.1107/S2056989015020502

Crystal structure of (E)-N-[(2-meth­­oxy­naphthalen-1-yl)methyl­­idene]-3-nitro­aniline

Devika Bhai R.,a* C. R. Girija,b Shalini Sureshc and Ramakrishna Reddyb

aResearch & Development Centre, Bharathiar University, Coimbatore 641 046, India, bGovt. Science College, Nrupathunga Road, Bangalore 560 001, India, and cSSMRV College, Jayanagar 4th T block, Bangalore 560 041, India
*Correspondence e-mail: girijashivakumar@rediffmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 20 October 2015; accepted 29 October 2015; online 14 November 2015)

In the title compound, C18H14N2O3, the dihedral angle between the naphthalene ring system and the benzene ring is 59.99 (13)°. A short intra­molecular C—H⋯N contact closes an S(6) ring. The nitro group is disordered over two orientations in a statistical ratio. In the crystal, weak C—H⋯O hydrogen bonds and very weak π–π stacking inter­actions [centroid–centroid separation = 3.9168 (17) Å] are observed.

CCDC reference: 1429914

Similar articles

1. Related literature

For background to Schiff bases, see: Tolulope et al. (2013[Tolulope, M., Fasina, R. & Dada, O. (2013). J. Chem. Pharm. Res. 5, 177-181.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C18H14N2O3

  • Mr = 306.31

  • Monoclinic, P 21 /c

  • a = 12.8481 (7) Å

  • b = 15.4085 (6) Å

  • c = 7.6232 (3) Å

  • β = 98.040 (4)°

  • V = 1494.33 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.35 × 0.30 × 0.25 mm

2.2. Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.957, Tmax = 0.989

  • 21149 measured reflections

  • 2622 independent reflections

  • 1646 reflections with I > 2σ(I)

  • Rint = 0.046

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.143

  • S = 1.14

  • 2622 reflections

  • 227 parameters

  • 42 restraints

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C16—H16⋯N2 0.93 2.31 2.961 (3) 127
C13—H13⋯O1′i 0.93 2.49 3.318 (14) 148
C18—H18A⋯O2ii 0.96 2.46 3.135 (18) 127
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: SHELXL2014.

Supporting information

CCDC reference: 1429914

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015020502/hb7529sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015020502/hb7529Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015020502/hb7529Isup3.cml

checkCIF report


Chemical context top

Schiff bases are considered an important class of organic compounds, which have wide applications. In recent years, they have gained significant inter­est in the area of drug research and development owing to the broad bioactivities such as insecticidal, anti­bacterial, anti­tuberculosis and anti­microbial reported for the compounds and their metal complexes. These compounds play an important role in biological systems and are observed in various enzymes such as transaminases, tryptophan synthase etc. The important physical and biological properties of these compounds are related to the presence of the intra­molecular hydrogen bond and proton transfer equilibrium. Schiff bases have also been utilized as ligands to synthesize metal complexes with inter­esting applications. The steric and inductive effects introduced by substituents present on the aromatic portion of the Schiff base can influence the properties of the ligand significantly. In continuation of our efforts in understanding the role of subtle electronic variations such as substituent effects on Chemistry and activity of Schiff bases and their metal complexes, we herein report the crystal structure of Schiff base derived from 3-nitro­aniline and 2-meth­oxy naphthaldehyde (Tolulope et al., 2013).

Structural commentary top

The molecule of title compound is non-planar, with a dihedral angle between the naphthyl and phenyl aromatic rings of 59.99 (13)°, in which the two rings are twisted from one another. The C9—O3 single bond of 1.358 (3) Å and the C7═N2 double bond of 1.261 (3) Å .The bond angle of C5—N2—C7 of the imine group is 117.5 (2)°, less than 120°. The bond length of the nitro group is N1—O2(1.241 (6)Å) and N1—O1(1.239 (6)Å) and bond angle in O2—N1—O1 is 123.4 (12)° which is more than the planar bond angle of 120°. The torsion angles C8—C7—N2—C5 is 178.1 (2)°.These values support that the configurations about the N2=C7 bond is anti­(E-form), which is in accordance with the enol-imine tautomeric form.

Supra­molecular features top

The title compound has an intra molecular C16— H16···N2 hydrogen bond forming an S(6) motif (Table 2). Also there is a C—H···O inter­molecular inter­action, in which a C—H of the naphthyl ring of one molecule and O-atom of the nitro group of another molecule are linked to one another.

Synthesis and crystallization top

The block-like, yellow single crystals of the compound C18 H14 N2 O3, were grown using 1:1 mixture of CHCl3 and methanol as solvent by slow evaporation technique.

Refinement top

The hydrogen atoms in the structure were positioned geometrically (C—H = 0.93–0.98 Å. N—H = 0.86Å) and were refined using a riding model with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl and 1.2 for all other atoms. The two oxygen atoms of the nitro group are disordered over two orientations. The SADI, SIMU, and ISOR commands in SHELXL (Sheldrick, 2015) were used to model the disorder.

Crystal data, data collection and structure refinement details are summarized in Table 1.

Related literature top

For background to Schiff bases, see: Tolulope et al. (2013).

Structure description top

Schiff bases are considered an important class of organic compounds, which have wide applications. In recent years, they have gained significant inter­est in the area of drug research and development owing to the broad bioactivities such as insecticidal, anti­bacterial, anti­tuberculosis and anti­microbial reported for the compounds and their metal complexes. These compounds play an important role in biological systems and are observed in various enzymes such as transaminases, tryptophan synthase etc. The important physical and biological properties of these compounds are related to the presence of the intra­molecular hydrogen bond and proton transfer equilibrium. Schiff bases have also been utilized as ligands to synthesize metal complexes with inter­esting applications. The steric and inductive effects introduced by substituents present on the aromatic portion of the Schiff base can influence the properties of the ligand significantly. In continuation of our efforts in understanding the role of subtle electronic variations such as substituent effects on Chemistry and activity of Schiff bases and their metal complexes, we herein report the crystal structure of Schiff base derived from 3-nitro­aniline and 2-meth­oxy naphthaldehyde (Tolulope et al., 2013).

The molecule of title compound is non-planar, with a dihedral angle between the naphthyl and phenyl aromatic rings of 59.99 (13)°, in which the two rings are twisted from one another. The C9—O3 single bond of 1.358 (3) Å and the C7═N2 double bond of 1.261 (3) Å .The bond angle of C5—N2—C7 of the imine group is 117.5 (2)°, less than 120°. The bond length of the nitro group is N1—O2(1.241 (6)Å) and N1—O1(1.239 (6)Å) and bond angle in O2—N1—O1 is 123.4 (12)° which is more than the planar bond angle of 120°. The torsion angles C8—C7—N2—C5 is 178.1 (2)°.These values support that the configurations about the N2=C7 bond is anti­(E-form), which is in accordance with the enol-imine tautomeric form.

The title compound has an intra molecular C16— H16···N2 hydrogen bond forming an S(6) motif (Table 2). Also there is a C—H···O inter­molecular inter­action, in which a C—H of the naphthyl ring of one molecule and O-atom of the nitro group of another molecule are linked to one another.

For background to Schiff bases, see: Tolulope et al. (2013).

Synthesis and crystallization top

The block-like, yellow single crystals of the compound C18 H14 N2 O3, were grown using 1:1 mixture of CHCl3 and methanol as solvent by slow evaporation technique.

Refinement details top

The hydrogen atoms in the structure were positioned geometrically (C—H = 0.93–0.98 Å. N—H = 0.86Å) and were refined using a riding model with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl and 1.2 for all other atoms. The two oxygen atoms of the nitro group are disordered over two orientations. The SADI, SIMU, and ISOR commands in SHELXL (Sheldrick, 2015) were used to model the disorder.

Crystal data, data collection and structure refinement details are summarized in Table 1.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top
[Figure 1] Fig. 1. Plot of the title compound showing the intramolecular C—H···N interaction as a dashed line.
[Figure 2] Fig. 2. Crystal packing diagram showing the C—H···N and C—H···O interactions as dashed lines
(E)-N-[(2-Methoxynaphthalen-1-yl)methylidene]-3-nitroaniline top
Crystal data top
C18H14N2O3Dx = 1.362 Mg m−3
Mr = 306.31Melting point: 407 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.8481 (7) ÅCell parameters from 5867 reflections
b = 15.4085 (6) Åθ = 2.6–29.9°
c = 7.6232 (3) ŵ = 0.09 mm−1
β = 98.040 (4)°T = 293 K
V = 1494.33 (12) Å3Block, yellow
Z = 40.35 × 0.30 × 0.25 mm
F(000) = 640
Data collection top
Bruker Kappa APEXII CCD
diffractometer		2622 independent reflections
Radiation source: fine-focus sealed tube1646 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ω and φ scanθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		h = −15→15
Tmin = 0.957, Tmax = 0.989k = −18→18
21149 measured reflectionsl = −9→8
Refinement top
Refinement on F242 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.143 w = 1/[σ2(Fo2) + (0.0403P)2 + 0.9181P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max < 0.001
2622 reflectionsΔρmax = 0.16 e Å−3
227 parametersΔρmin = −0.17 e Å−3
Crystal data top
C18H14N2O3V = 1494.33 (12) Å3
Mr = 306.31Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.8481 (7) ŵ = 0.09 mm−1
b = 15.4085 (6) ÅT = 293 K
c = 7.6232 (3) Å0.35 × 0.30 × 0.25 mm
β = 98.040 (4)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer		2622 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		1646 reflections with I > 2σ(I)
Tmin = 0.957, Tmax = 0.989Rint = 0.046
21149 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05542 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 1.14Δρmax = 0.16 e Å−3
2622 reflectionsΔρmin = −0.17 e Å−3
227 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.0584 (2)−0.09762 (18)0.7746 (4)0.0523 (7)
C2−0.0226 (2)−0.03905 (19)0.7675 (4)0.0523 (7)
H2−0.0893−0.05620.78770.063*
C3−0.0015 (2)0.0457 (2)0.7296 (4)0.0566 (8)
H3−0.05450.08700.72470.068*
C40.0976 (2)0.07014 (18)0.6986 (4)0.0517 (7)
H40.11030.12760.67100.062*
C50.17862 (19)0.01015 (18)0.7081 (3)0.0461 (7)
C60.1585 (2)−0.07494 (18)0.7487 (4)0.0498 (7)
H60.2118−0.11620.75830.060*
C70.2942 (2)0.07229 (17)0.5418 (4)0.0475 (7)
H70.23330.08230.46300.057*
C80.39198 (19)0.10445 (16)0.4875 (3)0.0430 (6)
C90.3839 (2)0.13912 (17)0.3178 (4)0.0485 (7)
C100.4724 (2)0.17407 (18)0.2520 (4)0.0571 (8)
H100.46580.19720.13830.069*
C110.5665 (2)0.17361 (19)0.3552 (4)0.0585 (8)
H110.62420.19700.31070.070*
C120.5808 (2)0.13905 (17)0.5278 (4)0.0480 (7)
C130.6798 (2)0.1397 (2)0.6330 (4)0.0622 (8)
H130.73720.16260.58700.075*
C140.6933 (2)0.1077 (2)0.7988 (5)0.0649 (9)
H140.75950.10820.86620.078*
C150.6069 (2)0.0736 (2)0.8696 (4)0.0622 (8)
H150.61610.05210.98470.075*
C160.5094 (2)0.07154 (18)0.7716 (4)0.0537 (7)
H160.45320.04840.82110.064*
C170.49240 (19)0.10383 (16)0.5969 (3)0.0424 (6)
C180.2726 (3)0.1775 (2)0.0501 (4)0.0753 (10)
H18A0.20060.1711−0.00230.113*
H18B0.28970.23810.06200.113*
H18C0.31760.1502−0.02420.113*
N10.0376 (2)−0.18893 (19)0.8121 (5)0.0849 (9)
N20.28245 (17)0.03270 (16)0.6825 (3)0.0544 (6)
O30.28735 (15)0.13796 (14)0.2188 (3)0.0669 (6)
O10.1053 (10)−0.2414 (9)0.778 (4)0.106 (5)0.50 (4)
O2−0.0433 (13)−0.2105 (10)0.869 (4)0.108 (5)0.50 (4)
O1'0.1105 (8)−0.2356 (11)0.876 (4)0.106 (5)0.50 (4)
O2'−0.0556 (6)−0.2107 (9)0.772 (3)0.097 (4)0.50 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0460 (16)0.0463 (17)0.0646 (19)−0.0062 (13)0.0072 (14)0.0025 (14)
C20.0372 (15)0.061 (2)0.0598 (18)−0.0039 (13)0.0102 (13)−0.0005 (15)
C30.0424 (16)0.059 (2)0.069 (2)0.0107 (14)0.0099 (14)0.0020 (15)
C40.0476 (16)0.0463 (16)0.0620 (18)−0.0013 (13)0.0096 (13)0.0044 (14)
C50.0354 (14)0.0553 (18)0.0477 (16)−0.0035 (13)0.0059 (12)−0.0008 (13)
C60.0393 (15)0.0476 (17)0.0625 (18)0.0038 (12)0.0077 (13)0.0042 (13)
C70.0418 (15)0.0458 (16)0.0548 (18)−0.0055 (12)0.0063 (13)−0.0008 (13)
C80.0444 (16)0.0331 (14)0.0543 (17)−0.0011 (11)0.0163 (13)−0.0015 (12)
C90.0487 (17)0.0414 (16)0.0577 (18)−0.0013 (12)0.0149 (14)−0.0002 (13)
C100.062 (2)0.0522 (18)0.0618 (19)−0.0004 (14)0.0238 (16)0.0072 (14)
C110.0534 (19)0.0560 (19)0.072 (2)−0.0088 (14)0.0310 (16)−0.0021 (15)
C120.0446 (16)0.0420 (16)0.0609 (18)−0.0049 (12)0.0196 (14)−0.0074 (13)
C130.0451 (18)0.072 (2)0.073 (2)−0.0127 (15)0.0206 (16)−0.0146 (17)
C140.0406 (17)0.081 (2)0.073 (2)−0.0059 (15)0.0070 (15)−0.0106 (18)
C150.0538 (19)0.073 (2)0.0598 (19)−0.0040 (16)0.0084 (15)0.0028 (16)
C160.0436 (16)0.0553 (18)0.0644 (19)−0.0043 (13)0.0146 (14)0.0028 (15)
C170.0420 (15)0.0313 (14)0.0567 (17)−0.0024 (11)0.0164 (13)−0.0051 (12)
C180.074 (2)0.091 (3)0.061 (2)−0.0056 (19)0.0080 (17)0.0119 (18)
N10.062 (2)0.0590 (19)0.136 (3)−0.0098 (16)0.021 (2)0.0112 (19)
N20.0412 (13)0.0627 (16)0.0610 (15)−0.0060 (11)0.0132 (11)0.0063 (13)
O30.0566 (13)0.0810 (15)0.0629 (13)−0.0057 (11)0.0072 (10)0.0200 (11)
O10.086 (5)0.061 (4)0.170 (12)0.014 (3)0.012 (6)0.019 (6)
O20.094 (6)0.071 (4)0.172 (12)−0.023 (4)0.066 (6)0.021 (8)
O1'0.083 (5)0.069 (5)0.165 (12)0.003 (4)0.008 (6)0.056 (7)
O2'0.074 (4)0.067 (4)0.153 (11)−0.025 (3)0.029 (4)0.002 (7)
Geometric parameters (Å, º) top
C1—C21.372 (4)C11—H110.9300
C1—C61.374 (4)C11—C121.407 (4)
C1—N11.468 (4)C12—C131.406 (4)
C2—H20.9300C12—C171.425 (3)
C2—C31.372 (4)C13—H130.9300
C3—H30.9300C13—C141.345 (4)
C3—C41.380 (4)C14—H140.9300
C4—H40.9300C14—C151.402 (4)
C4—C51.386 (4)C15—H150.9300
C5—C61.380 (4)C15—C161.366 (4)
C5—N21.418 (3)C16—H160.9300
C6—H60.9300C16—C171.410 (4)
C7—H70.9300C18—H18A0.9600
C7—C81.463 (3)C18—H18B0.9600
C7—N21.261 (3)C18—H18C0.9600
C8—C91.390 (4)C18—O31.412 (3)
C8—C171.435 (4)N1—O11.241 (6)
C9—C101.412 (4)N1—O21.227 (6)
C9—O31.358 (3)N1—O1'1.227 (6)
C10—H100.9300N1—O2'1.239 (6)
C10—C111.347 (4)
C2—C1—C6123.1 (3)C11—C12—C17118.9 (3)
C2—C1—N1118.7 (3)C13—C12—C11121.4 (3)
C6—C1—N1118.2 (3)C13—C12—C17119.7 (3)
C1—C2—H2121.2C12—C13—H13119.3
C3—C2—C1117.6 (3)C14—C13—C12121.4 (3)
C3—C2—H2121.2C14—C13—H13119.3
C2—C3—H3119.7C13—C14—H14120.2
C2—C3—C4120.7 (3)C13—C14—C15119.6 (3)
C4—C3—H3119.7C15—C14—H14120.2
C3—C4—H4119.6C14—C15—H15119.6
C3—C4—C5120.9 (3)C16—C15—C14120.9 (3)
C5—C4—H4119.6C16—C15—H15119.6
C4—C5—N2122.9 (2)C15—C16—H16119.4
C6—C5—C4118.8 (2)C15—C16—C17121.1 (3)
C6—C5—N2118.2 (2)C17—C16—H16119.4
C1—C6—C5118.9 (2)C12—C17—C8118.8 (2)
C1—C6—H6120.6C16—C17—C8124.0 (2)
C5—C6—H6120.6C16—C17—C12117.2 (2)
C8—C7—H7116.1H18A—C18—H18B109.5
N2—C7—H7116.1H18A—C18—H18C109.5
N2—C7—C8127.9 (3)H18B—C18—H18C109.5
C9—C8—C7116.0 (2)O3—C18—H18A109.5
C9—C8—C17119.2 (2)O3—C18—H18B109.5
C17—C8—C7124.8 (2)O3—C18—H18C109.5
C8—C9—C10121.2 (3)O1—N1—C1115.6 (9)
O3—C9—C8117.1 (2)O2—N1—C1121.0 (8)
O3—C9—C10121.7 (3)O2—N1—O1123.4 (12)
C9—C10—H10120.3O1'—N1—C1119.3 (8)
C11—C10—C9119.5 (3)O1'—N1—O2'126.6 (12)
C11—C10—H10120.3O2'—N1—C1114.1 (8)
C10—C11—H11118.7C7—N2—C5117.5 (2)
C10—C11—C12122.5 (3)C9—O3—C18119.7 (2)
C12—C11—H11118.7
C1—C2—C3—C40.5 (4)C9—C8—C17—C16179.0 (2)
C2—C1—C6—C5−2.1 (4)C9—C10—C11—C120.3 (4)
C2—C1—N1—O1164.6 (15)C10—C9—O3—C18−4.2 (4)
C2—C1—N1—O2−13.9 (19)C10—C11—C12—C13−179.8 (3)
C2—C1—N1—O1'−156.0 (17)C10—C11—C12—C17−0.6 (4)
C2—C1—N1—O2'24.5 (14)C11—C12—C13—C14179.1 (3)
C2—C3—C4—C5−1.1 (4)C11—C12—C17—C80.3 (4)
C3—C4—C5—C60.2 (4)C11—C12—C17—C16−178.6 (2)
C3—C4—C5—N2−178.1 (2)C12—C13—C14—C15−0.5 (5)
C4—C5—C6—C11.3 (4)C13—C12—C17—C8179.6 (2)
C4—C5—N2—C7−53.8 (4)C13—C12—C17—C160.6 (4)
C6—C1—C2—C31.1 (4)C13—C14—C15—C160.7 (5)
C6—C1—N1—O1−15.6 (15)C14—C15—C16—C17−0.2 (5)
C6—C1—N1—O2165.9 (18)C15—C16—C17—C8−179.3 (3)
C6—C1—N1—O1'23.9 (17)C15—C16—C17—C12−0.4 (4)
C6—C1—N1—O2'−155.6 (13)C17—C8—C9—C10−0.4 (4)
C6—C5—N2—C7127.9 (3)C17—C8—C9—O3179.7 (2)
C7—C8—C9—C10178.5 (2)C17—C12—C13—C14−0.1 (4)
C7—C8—C9—O3−1.4 (3)N1—C1—C2—C3−179.0 (3)
C7—C8—C17—C12−178.7 (2)N1—C1—C6—C5178.1 (3)
C7—C8—C17—C160.2 (4)N2—C5—C6—C1179.7 (2)
C8—C7—N2—C5178.1 (2)N2—C7—C8—C9174.4 (3)
C8—C9—C10—C110.2 (4)N2—C7—C8—C17−6.8 (4)
C8—C9—O3—C18175.7 (3)O3—C9—C10—C11−179.9 (3)
C9—C8—C17—C120.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···N20.932.312.961 (3)127
C13—H13···O1′i0.932.493.318 (14)148
C18—H18A···O2ii0.962.463.135 (18)127
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x, −y, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···N20.932.312.961 (3)127
C13—H13···O1'i0.932.493.318 (14)148
C18—H18A···O2ii0.962.463.135 (18)127
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x, −y, −z+1.
 

Acknowledgements

The authors thank the management RSST, R&D Centre Bhara­thiar University and the Principal of SSMRV Degree College for support. RDB thanks The Oxford College of Science for access to research facilities. The authors also thank the SAIF, IIT, Chennai for providing the XRD facility.

References

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 First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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 First citationTolulope, M., Fasina, R. & Dada, O. (2013). J. Chem. Pharm. Res. 5, 177–181.  Google Scholar

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ISSN: 2056-9890
Volume 71| Part 12| December 2015| Pages o941-o942
https://doi.org/10.1107/S2056989015020502
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