(E)-2,3-Dimethyl-N-(2-nitro­benzyl­idene)aniline

Tahir, M.N.; Tariq, M.I.; Ahmad, S.; Sarfraz, M.; Ather, A.Q.

doi:10.1107/S1600536810024165

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1817

doi:10.1107/S1600536810024165

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(E)-2,3-Dimethyl-N-(2-nitrobenzylidene)aniline

M. Nawaz Tahir,^a ^* Muhammad Ilyas Tariq,^b Shahbaz Ahmad,^b Muhammad Sarfraz ^b and Abdul Qayyum Ather ^c

^aDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^bDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, and ^cApplied Chemistry Research Center, PCSIR Laboratories Complex, Lahore 54600, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 9 June 2010; accepted 21 June 2010; online 26 June 2010)

In the title compound, C₁₅H₁₄N₂O₂, the 2,3-dimethylanilinic and benzaldehyde groups are planar, with r.m.s. deviations of 0.0101 and 0.0241 Å, respectively, and are oriented at a dihedral angle of 11.69 (3)°. The nitro group is inclined to the benzaldehyde group by 34.02 (9)°. The molecule adopts an E configuration about the C=N bond. In the crystal, molecules are linked via C—H⋯O interactions, giving rise to the formation of zigzag polymeric chains extending along [010]. They are also linked by C—H⋯π, and π–π interactions [centroid–centroid distance of 3.7185 (11) Å] involving symmetry-related aniline and benzene rings. The H atoms of the ortho-methyl group are disordered over two sites with a refined occupancy ratio of 0.69 (2):0.31 (2).

Related literature

For the crystal structures of similar compounds, see: Tahir et al. (2010 ); Tariq et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₂
M_r = 254.28
Monoclinic, P 2₁ /c
a = 12.2910 (6) Å
b = 15.1422 (9) Å
c = 7.3384 (3) Å
β = 107.091 (2)°
V = 1305.46 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.32 × 0.15 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.985, T_max = 0.987
10220 measured reflections
2362 independent reflections
1705 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.111
S = 1.03
2362 reflections
171 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O2ⁱ	0.96	2.51	3.438 (2)	162.00
C8—H8B⋯Cg1ⁱⁱ	0.96	2.89	3.680 (2)	141
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024165/su2187sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810024165/su2187Isup2.hkl

checkCIF report

Comment top

In continuation of our research on the synthesis and crystal structure analysis of various Schiff bases of 2,3-dimethylaniline (Tariq et al., 2010; Tahir et al., 2010), we report herein on the crystal structure of the title compound, where the nitro group is in the ortho position. This structure differs from that reported earlier (Tariq et al., 2010) for 2,3-dimethyl-N-[(E)-4-nitrobenzylidene]aniline, where the nitro group is in the para-position.

In the title molecule (Fig. 1) the 2,3-dimethylaniline group A (C1—C8/N1) is planar, to within 0.0101 Å, and the benzylidene group B (C9—C15) is also planar, to within 0.0241 Å. The dihedral angle between mean planes A and B is 11.69 (3)°. The nitro group (O1/N2/O2) is oriented at 34.02 (9)° with respect to the mean plane of the parent group B. The molecule adopts an E configuration about the C1═ N9 bond, whose bond length is 1.263 (2) Å. The bond lengths are comparable with those in the structures cited above.

In the crystal structure the molecules are linked by C—H···O interactions to form zigzag polymeric chains extending along [010] (Table 1, Fig. 2). There also exist C-H···π interactions, and π–π interactions [centroid-to-centroid distance = 3.7185 (11) Å] between symmetry related aniline benzene rings (Table 1).

Footnote for Table 1: Cg1 is the centroid of benzene ring (C1-C6).

Related literature top

For the crystal structures of similar compounds, see: Tahir et al. (2010); Tariq et al. (2010).

Experimental top

Equimolar quantities of 2,3-dimethylaniline and 2-nitrobenzaldehyde were refluxed in methanol for 45 min resulting in an orange solution. The solution was kept at RT and affoarded palepink rod-like crystals, suitable for X-ray diffraction analysis, after 24 h.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the molecular structuite of the title molecule, with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown as small circles of arbitrary radii.
	Fig. 2. A partial crystal packing which shows that molecules form polymeric chains extending along [010].

(E)-2,3-Dimethyl-N-(2-nitrobenzylidene)aniline top

Crystal data top

C₁₅H₁₄N₂O₂	F(000) = 536
M_r = 254.28	D_x = 1.294 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1705 reflections
a = 12.2910 (6) Å	θ = 2.2–25.3°
b = 15.1422 (9) Å	µ = 0.09 mm⁻¹
c = 7.3384 (3) Å	T = 296 K
β = 107.091 (2)°	Rod, pale pink
V = 1305.46 (11) Å³	0.32 × 0.15 × 0.15 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2362 independent reflections
Radiation source: fine-focus sealed tube	1705 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 8.10 pixels mm^-1	θ_max = 25.3°, θ_min = 2.2°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −18→18
T_min = 0.985, T_max = 0.987	l = −5→8
10220 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0511P)² + 0.2309P] where P = (F_o² + 2F_c²)/3
2362 reflections	(Δ/σ)_max < 0.001
171 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₂	V = 1305.46 (11) Å³
M_r = 254.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.2910 (6) Å	µ = 0.09 mm⁻¹
b = 15.1422 (9) Å	T = 296 K
c = 7.3384 (3) Å	0.32 × 0.15 × 0.15 mm
β = 107.091 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2362 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1705 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.987	R_int = 0.029
10220 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	Δρ_max = 0.13 e Å⁻³
2362 reflections	Δρ_min = −0.16 e Å⁻³
171 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.57216 (14)	0.48517 (10)	0.7186 (2)	0.0898 (6)
O2	0.66972 (12)	0.41328 (10)	0.5671 (3)	0.0865 (7)
N1	0.72326 (11)	0.16848 (9)	0.60756 (19)	0.0440 (4)
N2	0.59423 (13)	0.41809 (10)	0.6438 (2)	0.0602 (6)
C1	0.84205 (12)	0.15240 (10)	0.6480 (2)	0.0411 (5)
C2	0.88063 (13)	0.06562 (10)	0.6889 (2)	0.0432 (5)
C3	0.99754 (14)	0.04808 (12)	0.7314 (2)	0.0508 (6)
C4	1.07104 (15)	0.11659 (15)	0.7281 (3)	0.0629 (7)
C5	1.03219 (15)	0.20131 (14)	0.6825 (3)	0.0670 (8)
C6	0.91756 (14)	0.21936 (12)	0.6413 (3)	0.0541 (6)
C7	0.79775 (11)	−0.00684 (9)	0.6917 (3)	0.0630 (7)
C8	1.04291 (11)	−0.04434 (9)	0.7794 (3)	0.0704 (7)
C9	0.69105 (12)	0.23778 (11)	0.6723 (2)	0.0423 (5)
C10	0.56911 (12)	0.25563 (10)	0.6417 (2)	0.0398 (5)
C11	0.52334 (13)	0.34016 (11)	0.6387 (2)	0.0444 (5)
C12	0.41029 (14)	0.35494 (13)	0.6243 (3)	0.0556 (6)
C13	0.33943 (15)	0.28376 (14)	0.6115 (3)	0.0609 (7)
C14	0.38193 (15)	0.19944 (13)	0.6158 (3)	0.0596 (7)
C15	0.49477 (14)	0.18559 (11)	0.6304 (2)	0.0501 (6)
H4	1.14863	0.10520	0.75744	0.0755*
H5	1.08312	0.24631	0.67951	0.0804*
H6	0.89095	0.27645	0.60905	0.0649*
H7A	0.79909	−0.01850	0.82093	0.0945*	0.69 (2)
H7B	0.81863	−0.05936	0.63677	0.0945*	0.69 (2)
H7C	0.72254	0.01102	0.61921	0.0945*	0.69 (2)
H8A	1.12430	−0.04385	0.80782	0.1056*
H8B	1.01086	−0.08255	0.67275	0.1056*
H8C	1.02244	−0.06541	0.88832	0.1056*
H9	0.74495	0.27808	0.74006	0.0507*
H12	0.38266	0.41218	0.62325	0.0667*
H13	0.26279	0.29245	0.59991	0.0730*
H14	0.33385	0.15133	0.60884	0.0714*
H15	0.52174	0.12810	0.63275	0.0601*
H7D	0.74650	0.01276	0.75999	0.0945*	0.31 (2)
H7E	0.83851	−0.05791	0.75358	0.0945*	0.31 (2)
H7F	0.75525	−0.02168	0.56333	0.0945*	0.31 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0974 (12)	0.0457 (8)	0.1170 (13)	0.0068 (8)	0.0169 (9)	−0.0163 (8)
O2	0.0608 (9)	0.0664 (10)	0.1409 (15)	−0.0066 (7)	0.0428 (9)	0.0129 (9)
N1	0.0396 (7)	0.0394 (8)	0.0527 (8)	0.0020 (6)	0.0129 (6)	−0.0001 (6)
N2	0.0526 (9)	0.0436 (9)	0.0793 (11)	0.0034 (7)	0.0114 (8)	0.0045 (8)
C1	0.0369 (8)	0.0433 (9)	0.0425 (8)	0.0001 (7)	0.0109 (7)	−0.0041 (7)
C2	0.0447 (9)	0.0447 (10)	0.0398 (8)	0.0039 (7)	0.0117 (7)	−0.0027 (7)
C3	0.0464 (9)	0.0624 (11)	0.0427 (9)	0.0125 (8)	0.0119 (7)	−0.0040 (8)
C4	0.0397 (9)	0.0864 (15)	0.0628 (12)	0.0059 (10)	0.0152 (8)	−0.0087 (10)
C5	0.0492 (11)	0.0747 (14)	0.0821 (14)	−0.0164 (10)	0.0270 (9)	−0.0100 (11)
C6	0.0517 (10)	0.0456 (10)	0.0680 (11)	−0.0040 (8)	0.0222 (8)	−0.0034 (8)
C7	0.0612 (11)	0.0442 (11)	0.0811 (13)	−0.0018 (9)	0.0170 (10)	0.0018 (9)
C8	0.0676 (12)	0.0758 (14)	0.0636 (12)	0.0317 (11)	0.0127 (9)	0.0010 (10)
C9	0.0399 (9)	0.0414 (9)	0.0434 (9)	−0.0004 (7)	0.0088 (7)	−0.0006 (7)
C10	0.0394 (8)	0.0431 (9)	0.0367 (8)	0.0030 (7)	0.0108 (6)	−0.0007 (7)
C11	0.0425 (9)	0.0448 (9)	0.0463 (9)	−0.0001 (7)	0.0137 (7)	−0.0002 (7)
C12	0.0480 (10)	0.0585 (11)	0.0634 (11)	0.0117 (9)	0.0213 (8)	−0.0006 (9)
C13	0.0405 (9)	0.0798 (15)	0.0660 (12)	0.0026 (9)	0.0215 (8)	0.0020 (10)
C14	0.0493 (10)	0.0675 (13)	0.0632 (12)	−0.0134 (9)	0.0186 (9)	0.0005 (10)
C15	0.0505 (10)	0.0440 (10)	0.0547 (10)	−0.0020 (8)	0.0138 (8)	−0.0002 (8)

Geometric parameters (Å, º) top

O1—N2	1.222 (2)	C14—C15	1.375 (3)
O2—N2	1.221 (2)	C4—H4	0.9300
N1—C1	1.423 (2)	C5—H5	0.9300
N1—C9	1.263 (2)	C6—H6	0.9300
N2—C11	1.461 (2)	C7—H7A	0.9600
C1—C2	1.399 (2)	C7—H7B	0.9600
C1—C6	1.385 (2)	C7—H7C	0.9600
C2—C3	1.403 (2)	C7—H7D	0.9600
C2—C7	1.501 (2)	C7—H7E	0.9600
C3—C4	1.381 (3)	C7—H7F	0.9600
C3—C8	1.509 (2)	C8—H8A	0.9600
C4—C5	1.375 (3)	C8—H8B	0.9600
C5—C6	1.379 (3)	C8—H8C	0.9600
C9—C10	1.474 (2)	C9—H9	0.9300
C10—C11	1.396 (2)	C12—H12	0.9300
C10—C15	1.386 (2)	C13—H13	0.9300
C11—C12	1.381 (2)	C14—H14	0.9300
C12—C13	1.372 (3)	C15—H15	0.9300
C13—C14	1.376 (3)

O1···C15ⁱ	3.413 (2)	H6···C8^iv	2.8800
O1···N2ⁱⁱ	3.194 (2)	H7B···C8	2.6600
O1···O1ⁱⁱ	3.209 (2)	H7B···H8B	2.3300
O2···C9	2.758 (2)	H7B···H14^xi	2.5900
O1···H15ⁱ	2.8200	H7C···N1	2.3900
O1···H14ⁱ	2.9000	H7D···O2ⁱⁱⁱ	2.9100
O1···H7Fⁱⁱⁱ	2.9000	H7D···N1	2.5900
O1···H12	2.4900	H7D···H12^vi	2.5200
O2···H9	2.4400	H7E···H8C	2.1900
O2···H8A^iv	2.5100	H7E···H8B	2.3900
O2···H7D^v	2.9100	H7E···C8	2.4700
N1···C9^v	3.410 (2)	H7F···H14^xi	2.4200
N2···O1ⁱⁱ	3.194 (2)	H7F···O1^v	2.9000
N1···H7D	2.5900	H7F···N1	2.9400
N1···H7F	2.9400	H8A···H4	2.3200
N1···H15	2.6100	H8A···O2^ix	2.5100
N1···H9^v	2.9000	H8B···C7	2.9000
N1···H7C	2.3900	H8B···C3^viii	2.9800
N2···H9	2.7700	H8B···C4^viii	2.8600
C9···N1ⁱⁱⁱ	3.410 (2)	H8B···C5^viii	3.0800
C9···O2	2.758 (2)	H8B···H7B	2.3300
C13···C14ⁱⁱⁱ	3.591 (3)	H8B···H7E	2.3900
C14···C13^v	3.591 (3)	H8C···C7	2.8600
C15···O1^vi	3.413 (2)	H8C···C3^vii	2.8800
C1···H9^v	3.0700	H8C···H7E	2.1900
C2···H8C^vii	2.9800	H8C···C2^vii	2.9800
C3···H8C^vii	2.8800	H9···N2	2.7700
C3···H8B^viii	2.9800	H9···C6	2.5900
C4···H8B^viii	2.8600	H9···H6	2.2700
C5···H8B^viii	3.0800	H9···N1ⁱⁱⁱ	2.9000
C6···H9^v	3.0800	H9···C1ⁱⁱⁱ	3.0700
C6···H9	2.5900	H9···C6ⁱⁱⁱ	3.0800
C7···H8B	2.9000	H9···O2	2.4400
C7···H8C	2.8600	H12···H7Dⁱ	2.5200
C8···H7B	2.6600	H12···O1	2.4900
C8···H6^ix	2.8800	H13···H5^xii	2.5400
C8···H7E	2.4700	H14···H7B^xi	2.5900
C9···H6	2.7000	H14···O1^vi	2.9000
H4···H8A	2.3200	H14···H7F^xi	2.4200
H5···H13^x	2.5400	H15···O1^vi	2.8200
H6···C9	2.7000	H15···N1	2.6100
H6···H9	2.2700

C1—N1—C9	118.67 (14)	C1—C6—H6	120.00
O1—N2—O2	123.76 (17)	C5—C6—H6	120.00
O1—N2—C11	118.25 (16)	C2—C7—H7A	109.00
O2—N2—C11	117.94 (15)	C2—C7—H7B	109.00
N1—C1—C2	117.89 (14)	C2—C7—H7C	109.00
N1—C1—C6	121.64 (14)	C2—C7—H7D	109.00
C2—C1—C6	120.44 (15)	C2—C7—H7E	109.00
C1—C2—C3	119.06 (15)	C2—C7—H7F	109.00
C1—C2—C7	120.05 (14)	H7A—C7—H7B	109.00
C3—C2—C7	120.88 (14)	H7A—C7—H7C	109.00
C2—C3—C4	119.11 (17)	H7B—C7—H7C	109.00
C2—C3—C8	120.75 (15)	H7D—C7—H7E	109.00
C4—C3—C8	120.14 (16)	H7D—C7—H7F	109.00
C3—C4—C5	121.53 (18)	H7E—C7—H7F	109.00
C4—C5—C6	119.84 (19)	C3—C8—H8A	109.00
C1—C6—C5	119.95 (17)	C3—C8—H8B	109.00
N1—C9—C10	120.82 (14)	C3—C8—H8C	109.00
C9—C10—C11	123.90 (14)	H8A—C8—H8B	109.00
C9—C10—C15	119.45 (14)	H8A—C8—H8C	109.00
C11—C10—C15	116.43 (15)	H8B—C8—H8C	109.00
N2—C11—C10	120.39 (15)	N1—C9—H9	120.00
N2—C11—C12	116.77 (15)	C10—C9—H9	120.00
C10—C11—C12	122.81 (16)	C11—C12—H12	121.00
C11—C12—C13	118.85 (18)	C13—C12—H12	121.00
C12—C13—C14	119.89 (18)	C12—C13—H13	120.00
C13—C14—C15	120.70 (18)	C14—C13—H13	120.00
C10—C15—C14	121.32 (16)	C13—C14—H14	120.00
C3—C4—H4	119.00	C15—C14—H14	120.00
C5—C4—H4	119.00	C10—C15—H15	119.00
C4—C5—H5	120.00	C14—C15—H15	119.00
C6—C5—H5	120.00

C9—N1—C1—C2	140.61 (15)	C2—C3—C4—C5	−0.6 (3)
C9—N1—C1—C6	−41.5 (2)	C8—C3—C4—C5	179.15 (18)
C1—N1—C9—C10	−177.30 (13)	C3—C4—C5—C6	0.9 (3)
O1—N2—C11—C10	−149.86 (15)	C4—C5—C6—C1	0.7 (3)
O1—N2—C11—C12	32.3 (2)	N1—C9—C10—C11	−153.88 (15)
O2—N2—C11—C10	32.6 (2)	N1—C9—C10—C15	31.7 (2)
O2—N2—C11—C12	−145.21 (18)	C9—C10—C11—N2	7.4 (2)
N1—C1—C2—C3	−179.29 (13)	C9—C10—C11—C12	−174.92 (16)
N1—C1—C2—C7	−0.8 (2)	C15—C10—C11—N2	−178.04 (13)
C6—C1—C2—C3	2.8 (2)	C15—C10—C11—C12	−0.4 (2)
C6—C1—C2—C7	−178.69 (16)	C9—C10—C15—C14	175.24 (15)
N1—C1—C6—C5	179.62 (17)	C11—C10—C15—C14	0.4 (2)
C2—C1—C6—C5	−2.6 (3)	N2—C11—C12—C13	177.48 (17)
C1—C2—C3—C4	−1.2 (2)	C10—C11—C12—C13	−0.3 (3)
C1—C2—C3—C8	179.01 (15)	C11—C12—C13—C14	0.9 (3)
C7—C2—C3—C4	−179.72 (16)	C12—C13—C14—C15	−0.8 (3)
C7—C2—C3—C8	0.5 (2)	C13—C14—C15—C10	0.2 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1/2, z+1/2; (iv) −x+2, y+1/2, −z+3/2; (v) x, −y+1/2, z−1/2; (vi) −x+1, y−1/2, −z+3/2; (vii) −x+2, −y, −z+2; (viii) −x+2, −y, −z+1; (ix) −x+2, y−1/2, −z+3/2; (x) x+1, y, z; (xi) −x+1, −y, −z+1; (xii) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2^ix	0.96	2.51	3.438 (2)	162.00
C8—H8B···Cg1^viii	0.96	2.89	3.680 (2)	141

Symmetry codes: (viii) −x+2, −y, −z+1; (ix) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₂
M_r	254.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.2910 (6), 15.1422 (9), 7.3384 (3)
β (°)	107.091 (2)
V (Å³)	1305.46 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.15 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.985, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	10220, 2362, 1705
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.111, 1.03
No. of reflections	2362
No. of parameters	171
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.16

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2ⁱ	0.96	2.51	3.438 (2)	162.00
C8—H8B···Cg1ⁱⁱ	0.96	2.89	3.680 (2)	141

Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+2, −y, −z+1.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tahir, M. N., Tariq, M. I., Ahmad, S., Sarfraz, M. & Ather, A. Q. (2010). Acta Cryst. E66, o1562. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tariq, M. I., Ahmad, S., Tahir, M. N., Sarfaraz, M. & Hussain, I. (2010). Acta Cryst. E66, o1561. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 66| Part 7| July 2010| Page o1817

doi:10.1107/S1600536810024165

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