(E)-N-(Anthracen-9-yl­methyl­idene)-4-nitro­aniline

Geetha, K.; Kumar, D.K.A.P.; Lakshmanan, D.; Savitha, R.; Murugavel, S.

doi:10.1107/S1600536811035859

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2577

https://doi.org/10.1107/S1600536811035859

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(E)-N-(Anthracen-9-ylmethylidene)-4-nitroaniline

K. Geetha,^a ^* D. K. Andrew Prasanna Kumar,^b D. Lakshmanan,^c R. Savitha ^a and S. Murugavel ^d ^*

^aDepartment of Chemistry, SRM University, Vadapalani Campus, Chennai 600 026, India, ^bDepartment of Physics, Voorhees College, Vellore 632 001, India, ^cDepartment of Physics, C. Abdul Hakeem College of Engineering & Technology, Melvisharam, Vellore 632 509, India, and ^dDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India.
^*Correspondence e-mail: geethaorgchem@gmail.com, smurugavel27@gmail.com

(Received 21 August 2011; accepted 2 September 2011; online 14 September 2011)

In the title molecule, C₂₁H₁₄N₂O₂, the anthracenyl system is approximately planar [maximum deviation = 0.056 (4) Å] and is oriented at a dihedral angle of 73.6 (1)° with respect to the benzene ring. An intramolecular C—H⋯N hydrogen bond generates an S(6) ring motif. The crystal packing is stabilized by C—H⋯π and π–π interactions [centroid–centroid distances of 3.688 (2), 3.656 (1) and 3.716 (2) Å].

Related literature

For applications of anthracene derivatives, see: de Silva et al. (1997 ); Klarner et al. (1998 ); Han et al. (2009 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Arumugam et al. (2011 ); Villalpando et al. (2010 ).

Experimental

Crystal data

C₂₁H₁₄N₂O₂
M_r = 326.34
Triclinic, $[P \overline 1]$
a = 8.3634 (4) Å
b = 8.9045 (4) Å
c = 11.5119 (6) Å
α = 75.235 (2)°
β = 84.544 (3)°
γ = 75.054 (2)°
V = 800.56 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2004 ) T_min = 0.924, T_max = 0.991
15391 measured reflections
2983 independent reflections
1870 reflections with I > 2σ(I)
R_int = 0.151

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.306
S = 1.12
2983 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯N1	0.93	2.37	2.980 (4)	123
C20—H20⋯Cg1ⁱ	0.93	2.86	3.717 (3)	154
Symmetry code: (i) -x+1, -y+2, -z.

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: 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: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811035859/im2315sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035859/im2315Isup2.hkl

checkCIF report

Comment top

Anthracene is an attractive material in its photochemical and electrochemical properties and is used as a potential medium for photoconductive (de Silva et al., 1997) and electroluminescence (Klarner et al., 1998) devices. Furthermore, anthracene derivatives exhibited anticancer activity has also been reported recently (Han et al., 2009). Against this background and in order to obtain detailed information on molecular conformations in the solid state, X-ray studies of the title compound have been carried out.

Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The anthracene moiety (C1-C14) is essentially planar [maximum deviation = -0.056 (4) Å for the C11 atom] and shows a dihedral angle of 73.6 (1)° with respect to the (C16-C21) benzene ring. The nitro group is slightly twisted away from the plane of the attached benzene ring [C20-C19-N2-O1 = -4.9 (5) ° and C18-C19-N2-O2 = -6.7 (5) °]. The geometric parameters of the title molecule agrees well with those reported for similar structures (Arumugam et al., 2011, Villalpando et al., 2010).

In addition to van der Waals interactions, the crystal packing is stabilized by C-H···N and C-H···π hydrogen bonds as well as by π-π interactions. The intramolecular C12-H12···N1 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). The crystal packing (Fig. 2) is stabilized by C-H···π interactions between H20 and the neighbouring C1-C6 benzene ring, with a C20-H20···Cg1ⁱ separation of 2.86 Å (Fig. 2, Table 1; Cg1 is the centroid of the C1-C6 benzene ring, symmetry code as in Fig. 2). The molecular packing (Fig. 2) is further stabilized by π-π interactions with Cg1···Cg3ⁱⁱ, Cg2···Cg2ⁱⁱ and Cg2···Cg3ⁱⁱ separations of 3.688 (2) Å, 3.656 (1) Å and 3.716 (2) Å, respectively (Fig. 2; Cg1, Cg2 and Cg3 are the centroids of the C1-C6 benzene ring,C1/C6/C7/C8/C13/C14 benzene ring and C8-C13 benzene ring , respectively, symmetry code as in Fig. 2).

Related literature top

For applications of anthracene derivatives, see: de Silva et al. (1997); Klarner et al. (1998); Han et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Arumugam et al. (2011); Villalpando et al. (2010).

Experimental top

Equimolar amounts of p-nitroaniline and 9-anthracenecarboxaldehyde were suspended in ethanol at a concentration of 0.1 M and the reaction mixture was refluxed overnight under vigorous stirring. Afterwards the mixture was cooled down and filtered. Recrystallization of the crude product from hexane : CHCl₃ (1 : 1) yielded orange crystals of title compound (Yield 74 %).

Structure description top

For applications of anthracene derivatives, see: de Silva et al. (1997); Klarner et al. (1998); Han et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Arumugam et al. (2011); Villalpando et al. (2010).

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: 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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small cycles of arbitrary radius.
	Fig. 2. Intramolecular C-H···O, C-H···π and π-π interactions (dotted lines) in the title compound. Cg1, Cg2 and Cg3 are the centroids of the C1-C6 benzene ring, C1/C6/C7/C8/C13/C14 benzene ring and C8-C13 benzene ring , respectively. [Symmetry code: (i) 1-x, -y, 2-z; (ii) 1-x, -y, 1-z.]

(E)-N-(Anthracen-9-ylmethylidene)-4-nitroaniline top

Crystal data top

C₂₁H₁₄N₂O₂	Z = 2
M_r = 326.34	F(000) = 340
Triclinic, P1	D_x = 1.354 Mg m⁻³
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3634 (4) Å	Cell parameters from 5007 reflections
b = 8.9045 (4) Å	θ = 2.5–25.3°
c = 11.5119 (6) Å	µ = 0.09 mm⁻¹
α = 75.235 (2)°	T = 293 K
β = 84.544 (3)°	Flat, orange
γ = 75.054 (2)°	0.30 × 0.20 × 0.10 mm
V = 800.56 (7) Å³

Data collection top

Bruker APEXII diffractometer	2983 independent reflections
Radiation source: fine-focus sealed tube	1870 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.151
ω and φ scan	θ_max = 25.6°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker 2004)	h = −10→10
T_min = 0.924, T_max = 0.991	k = −10→10
15391 measured reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.306	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
2983 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₁H₁₄N₂O₂	γ = 75.054 (2)°
M_r = 326.34	V = 800.56 (7) Å³
Triclinic, P1	Z = 2
a = 8.3634 (4) Å	Mo Kα radiation
b = 8.9045 (4) Å	µ = 0.09 mm⁻¹
c = 11.5119 (6) Å	T = 293 K
α = 75.235 (2)°	0.30 × 0.20 × 0.10 mm
β = 84.544 (3)°

Data collection top

Bruker APEXII diffractometer	2983 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2004)	1870 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.991	R_int = 0.151
15391 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.306	H-atom parameters constrained
S = 1.12	Δρ_max = 0.45 e Å⁻³
2983 reflections	Δρ_min = −0.43 e Å⁻³
226 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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

	x	y	z	U_iso*/U_eq
C1	0.4268 (3)	−0.1323 (3)	0.7152 (2)	0.0507 (7)
C2	0.5139 (4)	−0.2566 (4)	0.8071 (2)	0.0622 (8)
H2	0.5912	−0.2354	0.8498	0.075*
C3	0.4872 (4)	−0.4052 (4)	0.8341 (3)	0.0725 (9)
H3	0.5463	−0.4840	0.8950	0.087*
C4	0.3730 (4)	−0.4430 (4)	0.7726 (3)	0.0746 (10)
H4	0.3553	−0.5455	0.7936	0.090*
C5	0.2885 (4)	−0.3314 (4)	0.6829 (3)	0.0673 (9)
H5	0.2134	−0.3579	0.6417	0.081*
C6	0.3125 (3)	−0.1725 (3)	0.6501 (2)	0.0532 (7)
C7	0.2314 (3)	−0.0591 (3)	0.5551 (2)	0.0549 (8)
H7	0.1599	−0.0875	0.5121	0.066*
C8	0.2524 (3)	0.0973 (3)	0.5211 (2)	0.0498 (7)
C9	0.1657 (3)	0.2116 (4)	0.4241 (2)	0.0621 (8)
H9	0.0979	0.1808	0.3798	0.075*
C10	0.1794 (4)	0.3636 (4)	0.3950 (3)	0.0703 (9)
H10	0.1211	0.4375	0.3312	0.084*
C11	0.2830 (4)	0.4104 (4)	0.4619 (3)	0.0675 (9)
H11	0.2904	0.5164	0.4427	0.081*
C12	0.3710 (3)	0.3050 (3)	0.5525 (2)	0.0588 (8)
H12	0.4395	0.3393	0.5939	0.071*
C13	0.3618 (3)	0.1421 (3)	0.5868 (2)	0.0487 (7)
C14	0.4501 (3)	0.0265 (3)	0.6825 (2)	0.0479 (7)
C15	0.5698 (3)	0.0602 (4)	0.7521 (3)	0.0584 (8)
H15	0.5835	0.0005	0.8311	0.070*
C16	0.7666 (3)	0.1767 (3)	0.7942 (2)	0.0553 (8)
C17	0.9203 (4)	0.1906 (4)	0.7470 (3)	0.0687 (9)
H17	0.9467	0.1877	0.6672	0.082*
C18	1.0355 (4)	0.2085 (4)	0.8158 (3)	0.0695 (9)
H18	1.1407	0.2147	0.7841	0.083*
C19	0.9936 (3)	0.2169 (3)	0.9316 (2)	0.0561 (8)
C20	0.8419 (3)	0.2054 (4)	0.9826 (2)	0.0597 (8)
H20	0.8168	0.2105	1.0622	0.072*
C21	0.7263 (3)	0.1859 (3)	0.9128 (2)	0.0589 (8)
H21	0.6214	0.1791	0.9451	0.071*
N1	0.6547 (3)	0.1602 (3)	0.7163 (2)	0.0647 (7)
N2	1.1188 (4)	0.2349 (4)	1.0045 (3)	0.0823 (9)
O1	1.0791 (4)	0.2499 (5)	1.1057 (3)	0.1296 (12)
O2	1.2591 (3)	0.2269 (4)	0.9629 (2)	0.1103 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0442 (15)	0.0651 (17)	0.0434 (14)	−0.0129 (12)	0.0062 (11)	−0.0174 (12)
C2	0.0615 (18)	0.076 (2)	0.0457 (15)	−0.0128 (14)	−0.0012 (13)	−0.0120 (13)
C3	0.087 (2)	0.070 (2)	0.0511 (17)	−0.0134 (17)	0.0044 (16)	−0.0059 (14)
C4	0.094 (3)	0.0552 (19)	0.073 (2)	−0.0245 (17)	0.0155 (18)	−0.0117 (15)
C5	0.0660 (19)	0.073 (2)	0.0698 (19)	−0.0249 (15)	0.0068 (15)	−0.0235 (16)
C6	0.0498 (16)	0.0619 (18)	0.0498 (15)	−0.0148 (13)	0.0074 (12)	−0.0187 (12)
C7	0.0490 (16)	0.0723 (19)	0.0503 (15)	−0.0204 (13)	−0.0009 (12)	−0.0218 (13)
C8	0.0412 (14)	0.0648 (17)	0.0423 (14)	−0.0115 (12)	0.0031 (11)	−0.0139 (12)
C9	0.0511 (17)	0.084 (2)	0.0502 (16)	−0.0143 (14)	−0.0074 (13)	−0.0139 (14)
C10	0.0645 (19)	0.076 (2)	0.0576 (18)	−0.0116 (15)	−0.0089 (15)	0.0030 (15)
C11	0.068 (2)	0.0588 (18)	0.0694 (19)	−0.0151 (15)	−0.0038 (15)	−0.0043 (14)
C12	0.0550 (17)	0.0650 (19)	0.0568 (17)	−0.0172 (13)	−0.0026 (13)	−0.0125 (13)
C13	0.0416 (14)	0.0623 (17)	0.0439 (14)	−0.0133 (12)	0.0062 (11)	−0.0176 (12)
C14	0.0405 (14)	0.0615 (17)	0.0428 (14)	−0.0133 (11)	0.0018 (11)	−0.0145 (12)
C15	0.0498 (16)	0.0717 (19)	0.0539 (16)	−0.0151 (14)	−0.0036 (12)	−0.0143 (13)
C16	0.0581 (17)	0.0556 (16)	0.0545 (16)	−0.0139 (12)	−0.0105 (13)	−0.0144 (12)
C17	0.0637 (19)	0.092 (2)	0.0553 (17)	−0.0213 (16)	0.0017 (14)	−0.0260 (15)
C18	0.0506 (17)	0.093 (2)	0.0633 (19)	−0.0197 (15)	0.0002 (14)	−0.0130 (15)
C19	0.0501 (16)	0.0639 (18)	0.0532 (16)	−0.0140 (13)	−0.0131 (13)	−0.0079 (12)
C20	0.0564 (18)	0.0771 (19)	0.0485 (15)	−0.0161 (14)	−0.0053 (13)	−0.0191 (13)
C21	0.0469 (15)	0.073 (2)	0.0600 (17)	−0.0187 (13)	0.0002 (13)	−0.0191 (14)
N1	0.0692 (16)	0.0745 (17)	0.0572 (14)	−0.0250 (13)	−0.0087 (12)	−0.0182 (12)
N2	0.068 (2)	0.113 (2)	0.0676 (18)	−0.0334 (16)	−0.0227 (15)	−0.0059 (16)
O1	0.100 (2)	0.225 (4)	0.093 (2)	−0.056 (2)	−0.0209 (17)	−0.069 (2)
O2	0.0675 (17)	0.169 (3)	0.097 (2)	−0.0584 (17)	−0.0212 (15)	0.0007 (17)

Geometric parameters (Å, º) top

C1—C2	1.418 (4)	C11—H11	0.9300
C1—C14	1.428 (4)	C12—C13	1.423 (4)
C1—C6	1.432 (4)	C12—H12	0.9300
C2—C3	1.352 (4)	C13—C14	1.415 (4)
C2—H2	0.9300	C14—C15	1.471 (4)
C3—C4	1.394 (5)	C15—N1	1.245 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.344 (5)	C16—C17	1.370 (4)
C4—H4	0.9300	C16—C21	1.393 (4)
C5—C6	1.430 (4)	C16—N1	1.414 (3)
C5—H5	0.9300	C17—C18	1.367 (4)
C6—C7	1.379 (4)	C17—H17	0.9300
C7—C8	1.399 (4)	C18—C19	1.361 (4)
C7—H7	0.9300	C18—H18	0.9300
C8—C9	1.415 (4)	C19—C20	1.364 (4)
C8—C13	1.430 (4)	C19—N2	1.466 (4)
C9—C10	1.341 (4)	C20—C21	1.385 (4)
C9—H9	0.9300	C20—H20	0.9300
C10—C11	1.412 (4)	C21—H21	0.9300
C10—H10	0.9300	N2—O1	1.212 (4)
C11—C12	1.342 (4)	N2—O2	1.216 (4)

C2—C1—C14	123.9 (2)	C11—C12—H12	119.2
C2—C1—C6	117.0 (2)	C13—C12—H12	119.2
C14—C1—C6	119.0 (2)	C14—C13—C12	124.0 (2)
C3—C2—C1	121.4 (3)	C14—C13—C8	119.4 (2)
C3—C2—H2	119.3	C12—C13—C8	116.6 (2)
C1—C2—H2	119.3	C13—C14—C1	120.3 (2)
C2—C3—C4	121.5 (3)	C13—C14—C15	123.2 (2)
C2—C3—H3	119.3	C1—C14—C15	116.5 (2)
C4—C3—H3	119.3	N1—C15—C14	126.8 (3)
C5—C4—C3	120.1 (3)	N1—C15—H15	116.6
C5—C4—H4	119.9	C14—C15—H15	116.6
C3—C4—H4	119.9	C17—C16—C21	119.2 (2)
C4—C5—C6	120.8 (3)	C17—C16—N1	117.1 (2)
C4—C5—H5	119.6	C21—C16—N1	123.6 (2)
C6—C5—H5	119.6	C18—C17—C16	120.9 (3)
C7—C6—C5	121.2 (3)	C18—C17—H17	119.6
C7—C6—C1	119.6 (2)	C16—C17—H17	119.6
C5—C6—C1	119.2 (3)	C19—C18—C17	118.9 (3)
C6—C7—C8	122.5 (2)	C19—C18—H18	120.5
C6—C7—H7	118.8	C17—C18—H18	120.5
C8—C7—H7	118.8	C18—C19—C20	122.6 (3)
C7—C8—C9	121.2 (2)	C18—C19—N2	118.3 (3)
C7—C8—C13	119.1 (2)	C20—C19—N2	119.1 (3)
C9—C8—C13	119.7 (2)	C19—C20—C21	118.2 (3)
C10—C9—C8	121.3 (3)	C19—C20—H20	120.9
C10—C9—H9	119.3	C21—C20—H20	120.9
C8—C9—H9	119.3	C20—C21—C16	120.1 (3)
C9—C10—C11	119.4 (3)	C20—C21—H21	119.9
C9—C10—H10	120.3	C16—C21—H21	119.9
C11—C10—H10	120.3	C15—N1—C16	120.0 (2)
C12—C11—C10	121.4 (3)	O1—N2—O2	123.0 (3)
C12—C11—H11	119.3	O1—N2—C19	118.2 (3)
C10—C11—H11	119.3	O2—N2—C19	118.7 (3)
C11—C12—C13	121.6 (3)

C14—C1—C2—C3	−179.8 (2)	C8—C13—C14—C1	−1.7 (4)
C6—C1—C2—C3	−1.6 (4)	C12—C13—C14—C15	−4.1 (4)
C1—C2—C3—C4	0.1 (5)	C8—C13—C14—C15	177.7 (2)
C2—C3—C4—C5	1.1 (5)	C2—C1—C14—C13	177.9 (2)
C3—C4—C5—C6	−0.7 (5)	C6—C1—C14—C13	−0.2 (4)
C4—C5—C6—C7	177.4 (3)	C2—C1—C14—C15	−1.5 (4)
C4—C5—C6—C1	−0.8 (4)	C6—C1—C14—C15	−179.6 (2)
C2—C1—C6—C7	−176.3 (2)	C13—C14—C15—N1	−28.3 (4)
C14—C1—C6—C7	2.0 (4)	C1—C14—C15—N1	151.1 (3)
C2—C1—C6—C5	2.0 (4)	C21—C16—C17—C18	2.0 (5)
C14—C1—C6—C5	−179.8 (2)	N1—C16—C17—C18	179.4 (3)
C5—C6—C7—C8	179.9 (2)	C16—C17—C18—C19	−1.8 (5)
C1—C6—C7—C8	−1.8 (4)	C17—C18—C19—C20	1.2 (5)
C6—C7—C8—C9	−179.2 (2)	C17—C18—C19—N2	179.6 (3)
C6—C7—C8—C13	0.0 (4)	C18—C19—C20—C21	−0.7 (5)
C7—C8—C9—C10	176.7 (3)	N2—C19—C20—C21	−179.0 (2)
C13—C8—C9—C10	−2.4 (4)	C19—C20—C21—C16	0.8 (4)
C8—C9—C10—C11	0.4 (4)	C17—C16—C21—C20	−1.4 (4)
C9—C10—C11—C12	1.4 (5)	N1—C16—C21—C20	−178.6 (2)
C10—C11—C12—C13	−1.1 (5)	C14—C15—N1—C16	−179.1 (2)
C11—C12—C13—C14	−179.2 (2)	C17—C16—N1—C15	136.4 (3)
C11—C12—C13—C8	−1.0 (4)	C21—C16—N1—C15	−46.3 (4)
C7—C8—C13—C14	1.8 (4)	C18—C19—N2—O1	176.6 (3)
C9—C8—C13—C14	−179.0 (2)	C20—C19—N2—O1	−4.9 (5)
C7—C8—C13—C12	−176.5 (2)	C18—C19—N2—O2	−6.7 (5)
C9—C8—C13—C12	2.7 (4)	C20—C19—N2—O2	171.8 (3)
C12—C13—C14—C1	176.5 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N1	0.93	2.37	2.980 (4)	123
C20—H20···Cg1ⁱ	0.93	2.86	3.717 (3)	154

Symmetry code: (i) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄N₂O₂
M_r	326.34
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.3634 (4), 8.9045 (4), 11.5119 (6)
α, β, γ (°)	75.235 (2), 84.544 (3), 75.054 (2)
V (Å³)	800.56 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 2004)
T_min, T_max	0.924, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	15391, 2983, 1870
R_int	0.151
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.306, 1.12
No. of reflections	2983
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.43

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia (1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N1	0.93	2.37	2.980 (4)	123
C20—H20···Cg1ⁱ	0.93	2.86	3.717 (3)	154

Symmetry code: (i) −x+1, −y+2, −z.

Acknowledgements

SM and KG thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

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