N-[(E)-1,3-Benzodioxol-5-yl­methyl­idene]-4-methyl­aniline

Tahir, M.N.; Shad, H.A.; Khan, M.N.; Tariq, R.H.

doi:10.1107/S1600536810048038

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3293

https://doi.org/10.1107/S1600536810048038

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N-[(E)-1,3-Benzodioxol-5-ylmethylidene]-4-methylaniline

M. Nawaz Tahir,^a ^* Hazoor Ahmad Shad,^b Muhammad Naeem Khan ^c and Riaz H. Tariq ^d

^aDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^bDepartment of Chemistry, Govt. M. D. College, Toba Tek Singh, Punjab, Pakistan, ^cApplied Chemistry Research Center, PCSIR Laboratories Complex, Lahore 54600, Pakistan, and ^dInstitute of Chemical and Pharmaceutical Sciences, The University of Faisalabad, Faisalabad, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 15 November 2010; accepted 18 November 2010; online 24 November 2010)

The two symmetry-independent molecules in the asymmetric unit of the title compound, C₁₅H₁₃NO₂, differ in conformation, with the virtually planar 4-methylaniline (r.m.s. deviations of 0.0511 and 0.0082 Å) and piperonal groups (r.m.s. deviations of 0.0241 and 0.0486 Å) forming dihedral angles of 19.40 (5) and 42.90 (6)°. In the crystal, molecules are linked by C—H⋯O and C—H⋯π interactions. The H atoms of the two methyl groups are disordered over two sets of sites of equal occupancy.

Related literature

For background to our ongoing project on the synthesis of various Schiff bases of piperonal and then their metal complexation and for a related structure, see: Tahir et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₃NO₂
M_r = 239.26
Triclinic, $[P \overline 1]$
a = 10.6914 (4) Å
b = 10.7680 (3) Å
c = 13.3332 (5) Å
α = 89.443 (2)°
β = 67.112 (2)°
γ = 62.534 (1)°
V = 1227.41 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.32 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.980, T_max = 0.988
18069 measured reflections
4417 independent reflections
3294 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.110
S = 1.03
4417 reflections
323 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3, Cg5 and Cg6 are the centroids of the C9–C14, C16–C21 and C24–C29 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28⋯O2ⁱ	0.93	2.59	3.447 (2)	153
C17—H17⋯Cg3ⁱⁱ	0.93	2.73	3.5306 (16)	145
C22—H22B⋯Cg5ⁱⁱ	0.96	2.86	3.5480 (18)	130
C22—H22D⋯Cg5ⁱⁱ	0.96	2.71	3.5480 (18)	146
C22—H22E⋯Cg6ⁱⁱⁱ	0.96	2.91	3.8610 (18)	169
Symmetry codes: (i) x-1, y+2, z; (ii) -x+1, -y+1, -z; (iii) x+1, y-1, z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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: https://doi.org/10.1107/S1600536810048038/gk2324sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048038/gk2324Isup2.hkl

checkCIF report

Comment top

The title compound (I, Fig. 1) is being reported as a part of our ongoing project related to synthesis of various Schiff bases of piperonal and then their metal complexation (Tahir et al., 2010).

The title compound consists of two molecules in the crystallographic asymmetric unit which differ from each other geometrically. In one molecule, 4-methylanilinic group A (C1—C7/N1) and the piperonalic group B (C8—C15/O1/O2) are almost planar with r. m. s deviation of 0.0511 and 0.0241 Å, respectively. The dihedral angle between A/B is 42.90 (6)°. In second molecule, the 4-methylanilinic group C (C16—C22/N2) and the piperonalic group D (C23—C30/O3/O4) are also almost planar with r. m. s deviation of 0.0082 and 0.0486 Å, respectively. The dihedral angle between C/D is 19.40 (5)°. The molecules are interlinked through hydrogen bonds of C—H···O type (Table 1, Fig. 2). The C—H···π interactions (Table 1) play important role in consolidating the crystal packing. The H atoms of methyl groups are disordered over two set of sites with equal occupancy ratio.

Related literature top

For background to our ongoing project on the synthesis of various Schiff bases of piperonal and then their metal complexation and for a related structure, see: Tahir et al. (2010).

Experimental top

Equimolar quantities of 4-methylaniline and and piperonal were refluxed in methanol along with few drops of acetic acid as catalyst for 30 min resulting in orange yellow solution. The solution was kept at room temperature which affoarded orange yellow prisms after a week.

Structure description top

The title compound (I, Fig. 1) is being reported as a part of our ongoing project related to synthesis of various Schiff bases of piperonal and then their metal complexation (Tahir et al., 2010).

For background to our ongoing project on the synthesis of various Schiff bases of piperonal and then their metal complexation and for a related structure, see: Tahir et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 title compound with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 2. The partial crystal packing (PLATON; Spek, 2009)

N-[(E)-1,3-Benzodioxol-5-ylmethylidene]-4-methylaniline top

Crystal data top

C₁₅H₁₃NO₂	Z = 4
M_r = 239.26	F(000) = 504
Triclinic, P1	D_x = 1.295 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6914 (4) Å	Cell parameters from 3294 reflections
b = 10.7680 (3) Å	θ = 2.2–25.3°
c = 13.3332 (5) Å	µ = 0.09 mm⁻¹
α = 89.443 (2)°	T = 296 K
β = 67.112 (2)°	Prisms, yellow
γ = 62.534 (1)°	0.32 × 0.22 × 0.18 mm
V = 1227.41 (8) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	4417 independent reflections
Radiation source: fine-focus sealed tube	3294 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 8.20 pixels mm^-1	θ_max = 25.3°, θ_min = 2.8°
ω scans	h = −11→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
T_min = 0.980, T_max = 0.988	l = −16→16
18069 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.050P)² + 0.2009P] where P = (F_o² + 2F_c²)/3
4417 reflections	(Δ/σ)_max < 0.001
323 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₅H₁₃NO₂	γ = 62.534 (1)°
M_r = 239.26	V = 1227.41 (8) Å³
Triclinic, P1	Z = 4
a = 10.6914 (4) Å	Mo Kα radiation
b = 10.7680 (3) Å	µ = 0.09 mm⁻¹
c = 13.3332 (5) Å	T = 296 K
α = 89.443 (2)°	0.32 × 0.22 × 0.18 mm
β = 67.112 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4417 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3294 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.988	R_int = 0.026
18069 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.03	Δρ_max = 0.17 e Å⁻³
4417 reflections	Δρ_min = −0.15 e Å⁻³
323 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 esds 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	0.85323 (13)	0.05174 (12)	0.16217 (13)	0.0823 (5)
O2	0.84925 (13)	−0.15617 (11)	0.13086 (10)	0.0649 (4)
N1	0.27161 (15)	0.46441 (13)	0.35889 (10)	0.0525 (4)
C1	0.12804 (17)	0.59481 (15)	0.39573 (12)	0.0479 (5)
C2	0.10114 (18)	0.70402 (16)	0.46908 (13)	0.0545 (5)
C3	−0.0303 (2)	0.83722 (17)	0.50051 (14)	0.0594 (6)
C4	−0.1380 (2)	0.86823 (17)	0.45801 (14)	0.0603 (6)
C5	−0.1111 (2)	0.75802 (19)	0.38577 (16)	0.0702 (7)
C6	0.0193 (2)	0.62326 (18)	0.35508 (15)	0.0649 (6)
C7	−0.27620 (18)	1.01681 (13)	0.48639 (16)	0.0868 (8)
C8	0.27767 (15)	0.34643 (13)	0.33754 (12)	0.0518 (5)
C9	0.42524 (17)	0.21151 (15)	0.28682 (12)	0.0476 (5)
C10	0.56824 (18)	0.20906 (15)	0.25598 (13)	0.0527 (5)
C11	0.70124 (18)	0.08074 (16)	0.20435 (13)	0.0512 (5)
C12	0.69907 (18)	−0.04387 (14)	0.18398 (12)	0.0481 (5)
C13	0.56266 (19)	−0.04509 (16)	0.21265 (13)	0.0547 (6)
C14	0.42526 (19)	0.08612 (16)	0.26411 (13)	0.0534 (6)
C15	0.9484 (2)	−0.09882 (17)	0.12271 (18)	0.0729 (7)
O3	−0.35490 (13)	1.45856 (11)	0.39324 (10)	0.0723 (4)
O4	−0.34615 (13)	1.64734 (11)	0.31303 (10)	0.0668 (4)
N2	0.18413 (14)	1.00194 (12)	0.16824 (10)	0.0483 (4)
C16	0.31939 (16)	0.86467 (14)	0.12541 (12)	0.0431 (5)
C17	0.43932 (17)	0.81718 (16)	0.01782 (12)	0.0513 (5)
C18	0.56401 (18)	0.67969 (17)	−0.01516 (13)	0.0544 (5)
C19	0.57678 (17)	0.58422 (15)	0.05568 (13)	0.0499 (5)
C20	0.45610 (19)	0.63169 (16)	0.16171 (14)	0.0563 (6)
C21	0.32925 (18)	0.76868 (16)	0.19582 (13)	0.0532 (5)
C22	0.71353 (14)	0.43394 (12)	0.01711 (12)	0.0656 (6)
C23	0.18014 (14)	1.10785 (12)	0.12391 (11)	0.0479 (5)
C24	0.04255 (17)	1.25022 (14)	0.16788 (12)	0.0439 (5)
C25	−0.09113 (17)	1.27386 (15)	0.26267 (12)	0.0485 (5)
C26	−0.21271 (17)	1.40978 (15)	0.30257 (12)	0.0486 (5)
C27	−0.20845 (18)	1.52255 (15)	0.25424 (13)	0.0484 (5)
C28	−0.08194 (19)	1.50285 (16)	0.16051 (13)	0.0539 (6)
C29	0.04428 (18)	1.36396 (15)	0.11813 (13)	0.0512 (5)
C30	−0.4330 (2)	1.61064 (18)	0.40804 (17)	0.0795 (7)
H2	0.17288	0.68733	0.49767	0.0655*
H3	−0.04678	0.90784	0.55151	0.0712*
H5	−0.18260	0.77485	0.35692	0.0843*
H6	0.03349	0.55134	0.30662	0.0778*
H7A	−0.29853	1.06796	0.55526	0.1302*	0.500
H7B	−0.36576	1.01018	0.49375	0.1302*	0.500
H7C	−0.25211	1.06673	0.42819	0.1302*	0.500
H7D	−0.31240	1.02862	0.42953	0.1302*	0.500
H7E	−0.24517	1.08640	0.49106	0.1302*	0.500
H7F	−0.35883	1.02984	0.55661	0.1302*	0.500
H8	0.18479	0.34604	0.35484	0.0622*
H10	0.57163	0.29154	0.27028	0.0632*
H13	0.56126	−0.12878	0.19867	0.0656*
H14	0.32993	0.08964	0.28396	0.0640*
H15A	1.00499	−0.14057	0.16709	0.0875*
H15B	1.02381	−0.12057	0.04595	0.0875*
H17	0.43518	0.87851	−0.03190	0.0616*
H18	0.64236	0.64993	−0.08751	0.0653*
H20	0.46038	0.57005	0.21120	0.0676*
H21	0.24912	0.79690	0.26730	0.0638*
H22A	0.80663	0.43643	0.00573	0.0984*	0.500
H22B	0.72685	0.39048	−0.05150	0.0984*	0.500
H22C	0.69426	0.37915	0.07252	0.0984*	0.500
H22D	0.67853	0.36761	0.01210	0.0984*	0.500
H22E	0.75831	0.41356	0.06933	0.0984*	0.500
H22F	0.79090	0.42489	−0.05468	0.0984*	0.500
H23	0.26796	1.09409	0.06129	0.0575*
H25	−0.09608	1.19938	0.29667	0.0582*
H28	−0.08011	1.57831	0.12668	0.0647*
H29	0.13266	1.34664	0.05446	0.0615*
H30A	−0.43932	1.65312	0.47490	0.0954*
H30B	−0.53839	1.64639	0.41559	0.0954*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0454 (7)	0.0472 (7)	0.1337 (12)	−0.0163 (6)	−0.0273 (7)	−0.0082 (7)
O2	0.0563 (7)	0.0391 (6)	0.0825 (8)	−0.0145 (6)	−0.0256 (6)	0.0000 (5)
N1	0.0473 (8)	0.0487 (7)	0.0477 (8)	−0.0166 (6)	−0.0165 (6)	0.0037 (6)
C1	0.0435 (9)	0.0477 (8)	0.0422 (8)	−0.0183 (7)	−0.0143 (7)	0.0074 (7)
C2	0.0507 (10)	0.0553 (9)	0.0512 (9)	−0.0237 (8)	−0.0193 (8)	0.0069 (7)
C3	0.0606 (11)	0.0488 (9)	0.0530 (10)	−0.0229 (9)	−0.0151 (9)	0.0045 (7)
C4	0.0546 (10)	0.0490 (9)	0.0536 (10)	−0.0149 (8)	−0.0149 (8)	0.0145 (8)
C5	0.0645 (12)	0.0657 (11)	0.0755 (12)	−0.0200 (10)	−0.0410 (10)	0.0156 (10)
C6	0.0650 (12)	0.0556 (10)	0.0672 (11)	−0.0195 (9)	−0.0350 (10)	0.0022 (8)
C7	0.0789 (14)	0.0574 (11)	0.0812 (14)	−0.0085 (10)	−0.0263 (11)	0.0199 (10)
C8	0.0470 (9)	0.0536 (9)	0.0472 (9)	−0.0224 (8)	−0.0166 (7)	0.0104 (7)
C9	0.0474 (9)	0.0462 (8)	0.0435 (8)	−0.0203 (7)	−0.0181 (7)	0.0101 (6)
C10	0.0530 (10)	0.0398 (8)	0.0610 (10)	−0.0210 (8)	−0.0232 (8)	0.0034 (7)
C11	0.0450 (9)	0.0452 (8)	0.0600 (10)	−0.0202 (8)	−0.0222 (8)	0.0052 (7)
C12	0.0513 (10)	0.0371 (8)	0.0489 (9)	−0.0164 (7)	−0.0221 (7)	0.0080 (6)
C13	0.0666 (11)	0.0447 (8)	0.0590 (10)	−0.0321 (8)	−0.0276 (9)	0.0141 (7)
C14	0.0527 (10)	0.0549 (9)	0.0563 (10)	−0.0311 (8)	−0.0219 (8)	0.0166 (7)
C15	0.0519 (11)	0.0451 (9)	0.0973 (14)	−0.0146 (9)	−0.0212 (10)	0.0035 (9)
O3	0.0521 (7)	0.0471 (6)	0.0740 (8)	−0.0125 (6)	−0.0016 (6)	0.0077 (6)
O4	0.0593 (7)	0.0405 (6)	0.0775 (8)	−0.0121 (6)	−0.0237 (6)	0.0094 (5)
N2	0.0434 (7)	0.0425 (7)	0.0483 (7)	−0.0166 (6)	−0.0156 (6)	0.0054 (5)
C16	0.0385 (8)	0.0420 (8)	0.0451 (8)	−0.0178 (7)	−0.0172 (7)	0.0047 (6)
C17	0.0473 (9)	0.0499 (9)	0.0474 (9)	−0.0192 (8)	−0.0179 (8)	0.0118 (7)
C18	0.0413 (9)	0.0562 (9)	0.0484 (9)	−0.0171 (8)	−0.0119 (7)	0.0019 (7)
C19	0.0421 (9)	0.0448 (8)	0.0634 (10)	−0.0189 (7)	−0.0267 (8)	0.0049 (7)
C20	0.0604 (11)	0.0469 (9)	0.0606 (10)	−0.0241 (8)	−0.0285 (9)	0.0165 (8)
C21	0.0519 (10)	0.0502 (9)	0.0472 (9)	−0.0233 (8)	−0.0144 (8)	0.0089 (7)
C22	0.0526 (10)	0.0481 (9)	0.0890 (13)	−0.0156 (8)	−0.0355 (10)	0.0026 (8)
C23	0.0456 (9)	0.0484 (8)	0.0440 (8)	−0.0234 (7)	−0.0139 (7)	0.0039 (7)
C24	0.0464 (9)	0.0421 (8)	0.0430 (8)	−0.0214 (7)	−0.0197 (7)	0.0053 (6)
C25	0.0528 (9)	0.0399 (8)	0.0480 (9)	−0.0223 (7)	−0.0182 (8)	0.0091 (6)
C26	0.0445 (9)	0.0436 (8)	0.0481 (9)	−0.0186 (7)	−0.0151 (7)	0.0049 (7)
C27	0.0502 (9)	0.0380 (8)	0.0562 (9)	−0.0179 (7)	−0.0272 (8)	0.0072 (7)
C28	0.0661 (11)	0.0472 (9)	0.0588 (10)	−0.0325 (8)	−0.0315 (9)	0.0190 (7)
C29	0.0535 (10)	0.0519 (9)	0.0485 (9)	−0.0302 (8)	−0.0173 (8)	0.0101 (7)
C30	0.0655 (12)	0.0465 (10)	0.0794 (13)	−0.0093 (9)	−0.0105 (10)	0.0069 (9)

Geometric parameters (Å, º) top

O1—C11	1.371 (3)	C8—H8	0.9300
O1—C15	1.421 (2)	C10—H10	0.9300
O2—C12	1.372 (2)	C13—H13	0.9300
O2—C15	1.425 (3)	C14—H14	0.9300
O3—C26	1.377 (2)	C15—H15B	0.9700
O3—C30	1.426 (2)	C15—H15A	0.9700
O4—C27	1.373 (2)	C16—C17	1.394 (2)
O4—C30	1.427 (2)	C16—C21	1.385 (2)
N1—C1	1.417 (2)	C17—C18	1.378 (2)
N1—C8	1.271 (2)	C18—C19	1.386 (2)
N2—C16	1.416 (2)	C19—C20	1.383 (2)
N2—C23	1.2702 (17)	C19—C22	1.507 (2)
C1—C2	1.383 (2)	C20—C21	1.382 (2)
C1—C6	1.378 (3)	C23—C24	1.458 (2)
C2—C3	1.379 (2)	C24—C25	1.404 (2)
C3—C4	1.381 (3)	C24—C29	1.391 (2)
C4—C5	1.382 (3)	C25—C26	1.355 (2)
C4—C7	1.511 (2)	C26—C27	1.380 (2)
C5—C6	1.385 (3)	C27—C28	1.365 (3)
C8—C9	1.460 (2)	C28—C29	1.392 (2)
C9—C10	1.408 (3)	C17—H17	0.9300
C9—C14	1.387 (2)	C18—H18	0.9300
C10—C11	1.360 (2)	C20—H20	0.9300
C11—C12	1.384 (2)	C21—H21	0.9300
C12—C13	1.363 (3)	C22—H22A	0.9600
C13—C14	1.395 (2)	C22—H22B	0.9600
C2—H2	0.9300	C22—H22C	0.9600
C3—H3	0.9300	C22—H22D	0.9600
C5—H5	0.9300	C22—H22E	0.9600
C6—H6	0.9300	C22—H22F	0.9600
C7—H7D	0.9600	C23—H23	0.9300
C7—H7E	0.9600	C25—H25	0.9300
C7—H7A	0.9600	C28—H28	0.9300
C7—H7B	0.9600	C29—H29	0.9300
C7—H7C	0.9600	C30—H30A	0.9700
C7—H7F	0.9600	C30—H30B	0.9700

C11—O1—C15	106.38 (15)	O2—C15—H15A	110.00
C12—O2—C15	105.90 (13)	O2—C15—H15B	110.00
C26—O3—C30	105.62 (14)	O1—C15—H15A	110.00
C27—O4—C30	105.60 (12)	N2—C16—C17	125.51 (13)
C1—N1—C8	120.32 (17)	N2—C16—C21	116.66 (14)
C16—N2—C23	121.55 (14)	C17—C16—C21	117.79 (14)
N1—C1—C2	118.47 (17)	C16—C17—C18	120.24 (14)
N1—C1—C6	123.39 (15)	C17—C18—C19	122.32 (15)
C2—C1—C6	117.89 (16)	C18—C19—C20	116.99 (15)
C1—C2—C3	121.09 (19)	C18—C19—C22	121.24 (14)
C2—C3—C4	121.56 (17)	C20—C19—C22	121.74 (14)
C3—C4—C5	116.92 (17)	C19—C20—C21	121.48 (15)
C5—C4—C7	121.5 (2)	C16—C21—C20	121.15 (15)
C3—C4—C7	121.57 (17)	N2—C23—C24	122.21 (14)
C4—C5—C6	121.9 (2)	C23—C24—C25	119.96 (13)
C1—C6—C5	120.59 (18)	C23—C24—C29	120.34 (15)
N1—C8—C9	122.35 (17)	C25—C24—C29	119.68 (14)
C8—C9—C10	120.28 (15)	C24—C25—C26	117.21 (14)
C8—C9—C14	119.97 (18)	O3—C26—C25	127.71 (14)
C10—C9—C14	119.68 (15)	O3—C26—C27	109.61 (13)
C9—C10—C11	117.06 (16)	C25—C26—C27	122.69 (16)
O1—C11—C12	109.29 (15)	O4—C27—C26	109.96 (15)
O1—C11—C10	128.18 (17)	O4—C27—C28	128.39 (14)
C10—C11—C12	122.5 (2)	C26—C27—C28	121.64 (15)
O2—C12—C11	109.89 (17)	C27—C28—C29	116.57 (15)
O2—C12—C13	128.21 (15)	C24—C29—C28	122.18 (16)
C11—C12—C13	121.88 (15)	O3—C30—O4	108.15 (15)
C12—C13—C14	116.30 (17)	C16—C17—H17	120.00
C9—C14—C13	122.6 (2)	C18—C17—H17	120.00
O1—C15—O2	108.12 (17)	C17—C18—H18	119.00
C1—C2—H2	119.00	C19—C18—H18	119.00
C3—C2—H2	119.00	C19—C20—H20	119.00
C2—C3—H3	119.00	C21—C20—H20	119.00
C4—C3—H3	119.00	C16—C21—H21	119.00
C4—C5—H5	119.00	C20—C21—H21	119.00
C6—C5—H5	119.00	C19—C22—H22A	109.00
C5—C6—H6	120.00	C19—C22—H22B	109.00
C1—C6—H6	120.00	C19—C22—H22C	109.00
C4—C7—H7A	109.00	C19—C22—H22D	109.00
C4—C7—H7B	109.00	C19—C22—H22E	109.00
C4—C7—H7C	109.00	C19—C22—H22F	109.00
H7A—C7—H7B	109.00	H22A—C22—H22B	109.00
H7A—C7—H7C	109.00	H22A—C22—H22C	109.00
H7A—C7—H7D	141.00	H22A—C22—H22D	141.00
H7A—C7—H7E	56.00	H22A—C22—H22E	56.00
H7A—C7—H7F	56.00	H22A—C22—H22F	56.00
H7B—C7—H7C	109.00	H22B—C22—H22C	109.00
H7B—C7—H7D	56.00	H22B—C22—H22D	56.00
H7B—C7—H7E	141.00	H22B—C22—H22E	141.00
H7B—C7—H7F	56.00	H22B—C22—H22F	56.00
H7C—C7—H7D	56.00	H22C—C22—H22D	56.00
H7C—C7—H7E	56.00	H22C—C22—H22E	56.00
H7C—C7—H7F	141.00	H22C—C22—H22F	141.00
H7D—C7—H7E	109.00	H22D—C22—H22E	109.00
H7D—C7—H7F	109.00	H22D—C22—H22F	109.00
H7E—C7—H7F	109.00	H22E—C22—H22F	109.00
C4—C7—H7F	109.00	N2—C23—H23	119.00
C4—C7—H7E	109.00	C24—C23—H23	119.00
C4—C7—H7D	109.00	C24—C25—H25	121.00
N1—C8—H8	119.00	C26—C25—H25	121.00
C9—C8—H8	119.00	C27—C28—H28	122.00
C9—C10—H10	121.00	C29—C28—H28	122.00
C11—C10—H10	121.00	C24—C29—H29	119.00
C12—C13—H13	122.00	C28—C29—H29	119.00
C14—C13—H13	122.00	O3—C30—H30A	110.00
C9—C14—H14	119.00	O3—C30—H30B	110.00
C13—C14—H14	119.00	O4—C30—H30A	110.00
O1—C15—H15B	110.00	O4—C30—H30B	110.00
H15A—C15—H15B	108.00	H30A—C30—H30B	108.00

C15—O1—C11—C10	176.76 (18)	C9—C10—C11—O1	176.83 (16)
C15—O1—C11—C12	−5.02 (19)	C9—C10—C11—C12	−1.2 (2)
C11—O1—C15—O2	6.6 (2)	C10—C11—C12—O2	179.84 (15)
C15—O2—C12—C11	2.67 (18)	C10—C11—C12—C13	1.3 (3)
C15—O2—C12—C13	−178.93 (17)	O1—C11—C12—C13	−177.02 (15)
C12—O2—C15—O1	−5.73 (19)	O1—C11—C12—O2	1.50 (18)
C26—O3—C30—O4	10.3 (2)	O2—C12—C13—C14	−178.49 (15)
C30—O3—C26—C27	−7.0 (2)	C11—C12—C13—C14	−0.3 (2)
C30—O3—C26—C25	173.0 (2)	C12—C13—C14—C9	−0.9 (2)
C27—O4—C30—O3	−9.8 (2)	N2—C16—C17—C18	−178.61 (19)
C30—O4—C27—C28	−175.6 (2)	C21—C16—C17—C18	−1.2 (3)
C30—O4—C27—C26	5.5 (2)	N2—C16—C21—C20	179.60 (19)
C1—N1—C8—C9	172.46 (13)	C17—C16—C21—C20	1.9 (3)
C8—N1—C1—C6	−38.5 (2)	C16—C17—C18—C19	−0.5 (3)
C8—N1—C1—C2	147.31 (16)	C17—C18—C19—C20	1.4 (3)
C16—N2—C23—C24	−179.17 (16)	C17—C18—C19—C22	179.34 (19)
C23—N2—C16—C21	161.80 (18)	C18—C19—C20—C21	−0.6 (3)
C23—N2—C16—C17	−20.7 (3)	C22—C19—C20—C21	−178.55 (19)
N1—C1—C2—C3	174.47 (15)	C19—C20—C21—C16	−1.0 (3)
C2—C1—C6—C5	1.1 (3)	N2—C23—C24—C25	0.4 (3)
N1—C1—C6—C5	−173.16 (17)	N2—C23—C24—C29	178.66 (17)
C6—C1—C2—C3	0.0 (3)	C23—C24—C25—C26	177.07 (17)
C1—C2—C3—C4	−1.8 (3)	C29—C24—C25—C26	−1.2 (3)
C2—C3—C4—C7	−175.81 (17)	C23—C24—C29—C28	−176.98 (18)
C2—C3—C4—C5	2.4 (3)	C25—C24—C29—C28	1.3 (3)
C3—C4—C5—C6	−1.4 (3)	C24—C25—C26—O3	179.66 (18)
C7—C4—C5—C6	176.84 (18)	C24—C25—C26—C27	−0.4 (3)
C4—C5—C6—C1	−0.3 (3)	O3—C26—C27—O4	1.0 (2)
N1—C8—C9—C14	−179.24 (15)	O3—C26—C27—C28	−178.02 (18)
N1—C8—C9—C10	−2.3 (2)	C25—C26—C27—O4	−179.03 (17)
C8—C9—C10—C11	−176.93 (14)	C25—C26—C27—C28	2.0 (3)
C14—C9—C10—C11	0.1 (2)	O4—C27—C28—C29	179.37 (19)
C10—C9—C14—C13	1.0 (2)	C26—C27—C28—C29	−1.9 (3)
C8—C9—C14—C13	177.97 (15)	C27—C28—C29—C24	0.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg3, Cg5 and Cg6 are the centroids of the C9–C14, C16–C21 and C24–C29 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···O2ⁱ	0.93	2.59	3.447 (2)	153
C17—H17···Cg3ⁱⁱ	0.93	2.73	3.5306 (16)	145
C22—H22B···Cg5ⁱⁱ	0.96	2.86	3.5480 (18)	130
C22—H22D···Cg5ⁱⁱ	0.96	2.71	3.5480 (18)	146
C22—H22E···Cg6ⁱⁱⁱ	0.96	2.91	3.8610 (18)	169

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃NO₂
M_r	239.26
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.6914 (4), 10.7680 (3), 13.3332 (5)
α, β, γ (°)	89.443 (2), 67.112 (2), 62.534 (1)
V (Å³)	1227.41 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.22 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.980, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	18069, 4417, 3294
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.110, 1.03
No. of reflections	4417
No. of parameters	323
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.15

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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

Cg3, Cg5 and Cg6 are the centroids of the C9–C14, C16–C21 and C24–C29 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···O2ⁱ	0.93	2.59	3.447 (2)	153
C17—H17···Cg3ⁱⁱ	0.93	2.73	3.5306 (16)	145
C22—H22B···Cg5ⁱⁱ	0.96	2.86	3.5480 (18)	130
C22—H22D···Cg5ⁱⁱ	0.96	2.71	3.5480 (18)	146
C22—H22E···Cg6ⁱⁱⁱ	0.96	2.91	3.8610 (18)	169

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

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 (2009). 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., Shad, H. A., Khan, M. N. & Tariq, M. I. (2010). Acta Cryst. E66, o2672. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 66| Part 12| December 2010| Page o3293

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