4-(4-Methoxy­phen­yl)-1-phenyl­pyridine-2,6(1H,3H)-dione

Das, U.; Chheda, S.B.; Pednekar, S.R.; Karambelkar, N.P.; Guru Row, T.N.

doi:10.1107/S1600536809017942

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1319

doi:10.1107/S1600536809017942

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4-(4-Methoxyphenyl)-1-phenylpyridine-2,6(1H,3H)-dione

Ushati Das,^a Shardul B. Chheda,^b Suhas R. Pednekar,^b Narendra P. Karambelkar ^c and T. N. Guru Row ^a ^*

^aSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India, ^bF-12, Organic Chemistry Research Laboratory, Ramanujan Ruia College, Matunga (East), Mumbai 400 019, India, and ^cJai Research Foundation, C-12, Road No. 16, Wagale Industrial Estate, Thane (West) 400 064, India
^*Correspondence e-mail: ssctng@sscu.iisc.ernet.in

(Received 13 April 2009; accepted 12 May 2009; online 20 May 2009)

In the title compound, C₁₈H₁₅NO₃, the pyridine-2,6-dione ring adopts an envelope conformation. The phenyl ring lies approximately perpendicular to the mean plane of the pyridine-2,6-dione ring [dihedral angle = 81.5 (1)°], while the methoxyphenyl ring is tilted to the same plane by a dihedral angle of 34.8 (1)°. Intermolecular C—H⋯O interactions link the molecules into chains along [100].

Related literature

For background literature concerning pyridine-2,6-diones, see: Kon & Nanji (1933 ). For ring conformation analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₈H₁₅NO₃
M_r = 293.31
Triclinic, $[P \overline 1]$
a = 7.4652 (5) Å
b = 9.0885 (7) Å
c = 11.1181 (8) Å
α = 77.384 (1)°
β = 88.747 (2)°
γ = 77.493 (1)°
V = 718.40 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 292 K
0.52 × 0.41 × 0.32 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.921, T_max = 0.970
7298 measured reflections
2714 independent reflections
2233 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.105
S = 0.91
2714 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2ⁱ	0.93	2.52	3.4260 (18)	164.00
C17—H17B⋯O1ⁱⁱ	0.96	2.55	3.073 (2)	114.00
Symmetry codes: (i) x-1, y, z; (ii) x, y-1, z+1.

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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 CAMERON (Watkin et al., 1993 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017942/bi2366sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017942/bi2366Isup2.hkl

checkCIF report

Comment top

The title compound belongs to the pyridine-2,6-dione family (Kon & Nanji, 1933). Pyridine-2,6-diones have a π-conjugated system and an extremely reactive methylene group, which has been exploited to carry out various condensations to form fused ring systems. The Mannich reaction is one of the important processes in medicinal chemistry that introduces an aminomethyl group, which acts as a pharmacophore when introduced into an appropriate substrate, and the title compound has been exploited via this reaction to form a wide array of compounds.

In the crystal structure, the pyridine-2,6-dione ring [N1/C10/C4/C2/C12/C11] adopts an envelope conformation (Cremer & Pople, 1975) with puckering parameters q₂ = 0.1394 (15)°, q₃ = 0.0581 (15)°, ϕ = 247.1 (6)°, puckering amplitude Q = 0.1510 (16) Å. The phenyl ring is nearly perpendicular to the pyridine-2,6-dione ring (torsion angle C11—N1—C7—C9 = 100.49 °) while the methoxy phenyl ring is tilted to the plane of the heterocyclic ring with a torsion angle C4—C2—C1—C6 = 31.14 °. Within the aryl rings, the C—C bonds are in the range of 1.343 (3) to 1.381 (3) Å, which is in accordance with those found in similar structures. The C—N single bonds (1.388 (3) to 1.448 (3) Å), C—O single bonds (1.365 (3) to 1.426 (3) Å), and C=O double bonds (1.213 (3) to 1.220 (2) Å) are within the usual range. The structure contains intermolecular C—H···O hydrogen bonds (see Table and Figure 2) which link the molecules into chains along the a axis. Alternating C—H···π and π···π interactions are also present (Figure 3).

Related literature top

For background literature concerning pyridine-2,6-diones, see: Kon & Nanji (1933). For details of the conformation of the heterocyclic ring, see: Cremer & Pople (1975).

Experimental top

The title compound was prepared by microwave treatment of 3-(4-methoxyphenyl)-2-pentene-1,5-dioic acid with acetic anhydride to form the corresponding dione, which was then reacted further with aniline to give the resultant compound (yield 96%). ¹H NMR (DMSO): δ 6.98 (m, 9H), 3.87 (s, 3H), 3.97(s, 2H), 6.67 (s, 1H).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004; 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 CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. Packing diagram viewed down the c axis. The dotted lines indicate intermolecular C—H···O interactions. H atoms not involved in these interactions are omitted.
	Fig. 3. Packing diagram viewed down the a axis. The dotted lines indicate intermolecular C—H···π and π···π interactions. H atoms not involved in these interactions are omitted.

4-(4-Methoxyphenyl)-1-phenylpyridine-2,6(1H,3H)-dione top

Crystal data top

C₁₈H₁₅NO₃	Z = 2
M_r = 293.31	F(000) = 308
Triclinic, P1	D_x = 1.356 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4652 (5) Å	Cell parameters from 2604 reflections
b = 9.0885 (7) Å	θ = 2.4–28.0°
c = 11.1181 (8) Å	µ = 0.09 mm⁻¹
α = 77.384 (1)°	T = 292 K
β = 88.747 (2)°	Block, colourless
γ = 77.493 (1)°	0.52 × 0.41 × 0.32 mm
V = 718.40 (9) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	2714 independent reflections
Radiation source: fine-focus sealed tube	2233 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 25.7°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.921, T_max = 0.970	k = −11→11
7298 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 0.91	w = 1/[σ²(F_o²) + (0.0537P)² + 0.2183P] where P = (F_o² + 2F_c²)/3
2714 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₈H₁₅NO₃	γ = 77.493 (1)°
M_r = 293.31	V = 718.40 (9) Å³
Triclinic, P1	Z = 2
a = 7.4652 (5) Å	Mo Kα radiation
b = 9.0885 (7) Å	µ = 0.09 mm⁻¹
c = 11.1181 (8) Å	T = 292 K
α = 77.384 (1)°	0.52 × 0.41 × 0.32 mm
β = 88.747 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	2714 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2233 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.970	R_int = 0.017
7298 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 0.91	Δρ_max = 0.15 e Å⁻³
2714 reflections	Δρ_min = −0.17 e Å⁻³
200 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
O1	0.43237 (14)	0.81573 (14)	−0.09890 (10)	0.0584 (4)
O2	1.00465 (13)	0.63224 (13)	0.07261 (10)	0.0538 (4)
O3	0.28108 (15)	0.25107 (13)	0.62184 (10)	0.0569 (4)
N1	0.72144 (15)	0.72212 (13)	−0.01738 (10)	0.0388 (4)
C1	0.49575 (18)	0.45771 (15)	0.29553 (12)	0.0369 (4)
C2	0.56872 (18)	0.54010 (15)	0.18235 (12)	0.0370 (4)
C3	0.3591 (2)	0.31101 (17)	0.51532 (13)	0.0418 (5)
C4	0.46008 (19)	0.63892 (17)	0.09213 (13)	0.0420 (5)
C5	0.5880 (2)	0.31397 (17)	0.36111 (13)	0.0428 (5)
C6	0.33201 (19)	0.52602 (17)	0.34314 (13)	0.0432 (5)
C7	0.79229 (18)	0.82360 (16)	−0.11708 (13)	0.0387 (4)
C8	0.2655 (2)	0.45429 (18)	0.45097 (14)	0.0465 (5)
C9	0.8359 (2)	0.95658 (17)	−0.09782 (14)	0.0462 (5)
C10	0.53018 (19)	0.73075 (16)	−0.01525 (13)	0.0406 (4)
C11	0.84395 (19)	0.62585 (16)	0.07338 (13)	0.0397 (5)
C12	0.77132 (19)	0.51251 (18)	0.16928 (13)	0.0446 (5)
C13	0.5210 (2)	0.24011 (17)	0.46966 (13)	0.0449 (5)
C14	0.8175 (2)	0.78459 (18)	−0.23010 (14)	0.0475 (5)
C15	0.9349 (2)	1.0118 (2)	−0.30544 (16)	0.0576 (6)
C16	0.8880 (2)	0.8799 (2)	−0.32436 (15)	0.0567 (6)
C17	0.3837 (3)	0.1142 (2)	0.70023 (15)	0.0585 (6)
C18	0.9086 (2)	1.04971 (19)	−0.19256 (16)	0.0541 (6)
H4	0.33372	0.64938	0.09840	0.0504*
H5	0.69755	0.26599	0.33143	0.0513*
H6	0.26674	0.62196	0.30098	0.0518*
H8	0.15638	0.50240	0.48115	0.0558*
H9	0.81648	0.98333	−0.02173	0.0554*
H12A	0.82601	0.50985	0.24829	0.0536*
H12B	0.81319	0.41097	0.15146	0.0536*
H13	0.58454	0.14339	0.51153	0.0539*
H14	0.78734	0.69496	−0.24275	0.0570*
H15	0.98420	1.07481	−0.36893	0.0692*
H16	0.90396	0.85501	−0.40126	0.0680*
H17A	0.50078	0.13092	0.72080	0.0878*
H17B	0.31768	0.08907	0.77430	0.0878*
H17C	0.40147	0.03050	0.65833	0.0878*
H18	0.94004	1.13880	−0.17976	0.0650*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0395 (6)	0.0727 (8)	0.0496 (6)	−0.0081 (5)	−0.0031 (5)	0.0114 (6)
O2	0.0335 (6)	0.0649 (7)	0.0596 (7)	−0.0153 (5)	−0.0013 (5)	−0.0016 (5)
O3	0.0537 (7)	0.0605 (7)	0.0484 (6)	−0.0121 (5)	0.0116 (5)	0.0042 (5)
N1	0.0332 (6)	0.0435 (7)	0.0380 (6)	−0.0104 (5)	0.0028 (5)	−0.0035 (5)
C1	0.0359 (7)	0.0391 (7)	0.0369 (7)	−0.0111 (6)	0.0015 (6)	−0.0081 (6)
C2	0.0363 (7)	0.0381 (7)	0.0382 (7)	−0.0104 (6)	0.0043 (6)	−0.0100 (6)
C3	0.0423 (8)	0.0474 (8)	0.0372 (8)	−0.0171 (7)	0.0044 (6)	−0.0056 (6)
C4	0.0311 (7)	0.0512 (9)	0.0434 (8)	−0.0120 (6)	0.0038 (6)	−0.0071 (7)
C5	0.0380 (8)	0.0453 (8)	0.0425 (8)	−0.0055 (6)	0.0057 (6)	−0.0083 (6)
C6	0.0403 (8)	0.0391 (8)	0.0454 (8)	−0.0057 (6)	0.0038 (6)	−0.0022 (6)
C7	0.0315 (7)	0.0421 (8)	0.0401 (8)	−0.0086 (6)	0.0009 (6)	−0.0035 (6)
C8	0.0379 (8)	0.0510 (9)	0.0481 (9)	−0.0074 (7)	0.0092 (7)	−0.0085 (7)
C9	0.0458 (9)	0.0458 (8)	0.0470 (9)	−0.0102 (7)	−0.0020 (7)	−0.0096 (7)
C10	0.0351 (7)	0.0454 (8)	0.0393 (8)	−0.0074 (6)	0.0007 (6)	−0.0061 (6)
C11	0.0345 (8)	0.0450 (8)	0.0401 (8)	−0.0086 (6)	0.0033 (6)	−0.0104 (6)
C12	0.0362 (8)	0.0514 (9)	0.0414 (8)	−0.0072 (6)	0.0013 (6)	−0.0021 (7)
C13	0.0465 (8)	0.0407 (8)	0.0434 (8)	−0.0067 (7)	−0.0006 (7)	−0.0029 (6)
C14	0.0451 (9)	0.0538 (9)	0.0471 (9)	−0.0167 (7)	0.0060 (7)	−0.0130 (7)
C15	0.0453 (9)	0.0647 (11)	0.0555 (10)	−0.0196 (8)	0.0034 (7)	0.0099 (8)
C16	0.0498 (10)	0.0783 (12)	0.0418 (9)	−0.0183 (9)	0.0090 (7)	−0.0094 (8)
C17	0.0640 (11)	0.0593 (10)	0.0460 (9)	−0.0164 (9)	0.0044 (8)	0.0046 (8)
C18	0.0501 (9)	0.0446 (9)	0.0655 (11)	−0.0177 (7)	−0.0054 (8)	0.0006 (8)

Geometric parameters (Å, º) top

O1—C10	1.2109 (18)	C11—C12	1.493 (2)
O2—C11	1.2133 (18)	C14—C16	1.379 (2)
O3—C3	1.3653 (18)	C15—C16	1.378 (2)
O3—C17	1.427 (2)	C15—C18	1.372 (2)
N1—C7	1.4485 (18)	C4—H4	0.930
N1—C10	1.4129 (19)	C5—H5	0.930
N1—C11	1.3886 (18)	C6—H6	0.930
C1—C2	1.4751 (19)	C8—H8	0.930
C1—C5	1.389 (2)	C9—H9	0.930
C1—C6	1.395 (2)	C12—H12A	0.970
C2—C4	1.341 (2)	C12—H12B	0.970
C2—C12	1.488 (2)	C13—H13	0.930
C3—C8	1.384 (2)	C14—H14	0.930
C3—C13	1.383 (2)	C15—H15	0.930
C4—C10	1.457 (2)	C16—H16	0.930
C5—C13	1.387 (2)	C17—H17A	0.960
C6—C8	1.372 (2)	C17—H17B	0.960
C7—C9	1.378 (2)	C17—H17C	0.960
C7—C14	1.377 (2)	C18—H18	0.930
C9—C18	1.380 (2)

O1···C14	3.1810 (19)	C17···H13	2.5500
O1···C17ⁱ	3.073 (2)	C18···H17Aⁱ	3.1000
O1···C5ⁱⁱ	3.3926 (19)	C18···H6^iv	2.9800
O2···C9	3.1501 (19)	H4···O2^x	2.5200
O2···O2ⁱⁱⁱ	3.1878 (16)	H4···C6	2.7100
O2···C11ⁱⁱⁱ	3.1383 (19)	H4···H6	2.2700
O1···H9^iv	2.8400	H5···C12	2.7000
O1···H17Bⁱ	2.5500	H5···H12A	2.5800
O2···H4^v	2.5200	H5···H12B	2.4000
O2···H12Bⁱⁱⁱ	2.8700	H5···C16ⁱⁱⁱ	3.1000
O2···H18^vi	2.7200	H6···C4	2.7000
O3···H12A^vii	2.8300	H6···H4	2.2700
C2···C10ⁱⁱ	3.592 (2)	H6···C18^iv	2.9800
C3···C6^vii	3.556 (2)	H6···H18^iv	2.5100
C4···C4ⁱⁱ	3.533 (2)	H8···H8^xi	2.3700
C5···O1ⁱⁱ	3.3926 (19)	H9···O1^iv	2.8400
C6···C3^vii	3.556 (2)	H12A···C5	2.8600
C9···O2	3.1501 (19)	H12A···H5	2.5800
C10···C2ⁱⁱ	3.592 (2)	H12A···O3^vii	2.8300
C11···C11ⁱⁱⁱ	3.533 (2)	H12B···C5	2.9300
C11···O2ⁱⁱⁱ	3.1383 (19)	H12B···H5	2.4000
C12···C14ⁱⁱⁱ	3.588 (2)	H12B···O2ⁱⁱⁱ	2.8700
C14···O1	3.1810 (19)	H12B···C14ⁱⁱⁱ	2.9700
C14···C12ⁱⁱⁱ	3.588 (2)	H13···C17	2.5500
C17···O1^viii	3.073 (2)	H13···H17A	2.3800
C1···H14ⁱⁱ	2.9000	H13···H17C	2.3200
C4···H6	2.7000	H14···C1ⁱⁱ	2.9000
C5···H12A	2.8600	H14···C6ⁱⁱ	2.8100
C5···H12B	2.9300	H14···C8ⁱⁱ	3.0000
C6···H4	2.7100	H17A···C13	2.7600
C6···H14ⁱⁱ	2.8100	H17A···C18^viii	3.1000
C8···H14ⁱⁱ	3.0000	H17A···H13	2.3800
C12···H5	2.7000	H17B···O1^viii	2.5500
C13···H17C^ix	3.0500	H17C···C13	2.7800
C13···H17C	2.7800	H17C···H13	2.3200
C13···H17A	2.7600	H17C···C13^ix	3.0500
C14···H12Bⁱⁱⁱ	2.9700	H18···O2^vi	2.7200
C16···H5ⁱⁱⁱ	3.1000	H18···H6^iv	2.5100

C3—O3—C17	117.96 (13)	C9—C18—C15	120.48 (16)
C7—N1—C10	118.12 (11)	C2—C4—H4	118.00
C7—N1—C11	118.34 (11)	C10—C4—H4	118.00
C10—N1—C11	123.50 (12)	C1—C5—H5	119.00
C2—C1—C5	122.31 (13)	C13—C5—H5	119.00
C2—C1—C6	120.23 (12)	C1—C6—H6	119.00
C5—C1—C6	117.42 (13)	C8—C6—H6	119.00
C1—C2—C4	122.65 (13)	C3—C8—H8	120.00
C1—C2—C12	118.18 (12)	C6—C8—H8	120.00
C4—C2—C12	119.17 (13)	C7—C9—H9	120.00
O3—C3—C8	115.66 (13)	C18—C9—H9	120.00
O3—C3—C13	125.04 (14)	C2—C12—H12A	108.00
C8—C3—C13	119.30 (14)	C2—C12—H12B	108.00
C2—C4—C10	123.24 (13)	C11—C12—H12A	108.00
C1—C5—C13	121.73 (14)	C11—C12—H12B	108.00
C1—C6—C8	121.22 (14)	H12A—C12—H12B	107.00
N1—C7—C9	120.00 (13)	C3—C13—H13	120.00
N1—C7—C14	119.30 (13)	C5—C13—H13	120.00
C9—C7—C14	120.69 (14)	C7—C14—H14	120.00
C3—C8—C6	120.67 (14)	C16—C14—H14	120.00
C7—C9—C18	119.36 (14)	C16—C15—H15	120.00
O1—C10—N1	119.66 (13)	C18—C15—H15	120.00
O1—C10—C4	123.20 (13)	C14—C16—H16	120.00
N1—C10—C4	117.10 (12)	C15—C16—H16	120.00
O2—C11—N1	120.80 (13)	O3—C17—H17A	109.00
O2—C11—C12	121.64 (13)	O3—C17—H17B	109.00
N1—C11—C12	117.54 (12)	O3—C17—H17C	109.00
C2—C12—C11	117.14 (13)	H17A—C17—H17B	109.00
C3—C13—C5	119.65 (14)	H17A—C17—H17C	110.00
C7—C14—C16	119.27 (15)	H17B—C17—H17C	109.00
C16—C15—C18	119.70 (16)	C9—C18—H18	120.00
C14—C16—C15	120.49 (15)	C15—C18—H18	120.00

C17—O3—C3—C8	−171.64 (14)	C1—C2—C4—C10	174.69 (13)
C17—O3—C3—C13	8.0 (2)	C12—C2—C4—C10	−4.8 (2)
C10—N1—C7—C9	100.50 (16)	C1—C2—C12—C11	−163.73 (12)
C10—N1—C7—C14	−80.33 (17)	C4—C2—C12—C11	15.8 (2)
C11—N1—C7—C9	−77.12 (17)	O3—C3—C8—C6	179.52 (14)
C11—N1—C7—C14	102.05 (16)	C13—C3—C8—C6	−0.1 (2)
C7—N1—C10—O1	3.7 (2)	O3—C3—C13—C5	−178.98 (14)
C7—N1—C10—C4	−174.06 (12)	C8—C3—C13—C5	0.6 (2)
C11—N1—C10—O1	−178.78 (14)	C2—C4—C10—O1	177.20 (15)
C11—N1—C10—C4	3.4 (2)	C2—C4—C10—N1	−5.1 (2)
C7—N1—C11—O2	3.7 (2)	C1—C5—C13—C3	−0.6 (2)
C7—N1—C11—C12	−174.81 (12)	C1—C6—C8—C3	−0.4 (2)
C10—N1—C11—O2	−173.76 (13)	N1—C7—C9—C18	178.01 (13)
C10—N1—C11—C12	7.7 (2)	C14—C7—C9—C18	−1.2 (2)
C5—C1—C2—C4	151.27 (15)	N1—C7—C14—C16	−178.87 (13)
C5—C1—C2—C12	−29.3 (2)	C9—C7—C14—C16	0.3 (2)
C6—C1—C2—C4	−31.1 (2)	C7—C9—C18—C15	0.9 (2)
C6—C1—C2—C12	148.33 (14)	O2—C11—C12—C2	164.44 (14)
C2—C1—C5—C13	177.76 (14)	N1—C11—C12—C2	−17.04 (19)
C6—C1—C5—C13	0.1 (2)	C7—C14—C16—C15	0.8 (2)
C2—C1—C6—C8	−177.30 (14)	C18—C15—C16—C14	−1.0 (2)
C5—C1—C6—C8	0.4 (2)	C16—C15—C18—C9	0.1 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2^x	0.93	2.52	3.4260 (18)	164.00
C17—H17B···O1^viii	0.96	2.55	3.073 (2)	114.00

Symmetry codes: (viii) x, y−1, z+1; (x) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅NO₃
M_r	293.31
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	7.4652 (5), 9.0885 (7), 11.1181 (8)
α, β, γ (°)	77.384 (1), 88.747 (2), 77.493 (1)
V (Å³)	718.40 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.52 × 0.41 × 0.32

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.921, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	7298, 2714, 2233
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.105, 0.91
No. of reflections	2714
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SAINT (Bruker, 2004, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.93	2.52	3.4260 (18)	164.00
C17—H17B···O1ⁱⁱ	0.96	2.55	3.073 (2)	114.00

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

Acknowledgements

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA–DST program at IISc.

References

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