4-(4-Meth­oxy­phen­yl)-6-methyl­amino-5-nitro-2-phenyl-4H-pyran-3-carbonitrile

Vishnupriya, R.; Suresh, J.; Sivakumar, S.; Kumar, R.R.; Lakshman, P.L.N.

doi:10.1107/S1600536813004923

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o451

doi:10.1107/S1600536813004923

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4-(4-Methoxyphenyl)-6-methylamino-5-nitro-2-phenyl-4H-pyran-3-carbonitrile

R. Vishnupriya,^a J. Suresh,^a S. Sivakumar,^b R. Ranjith Kumar ^b and P. L. Nilantha Lakshman ^c ^*

^aDepartment of Physics, The Madura College, Madurai 625 011, India, ^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: plakshmannilantha@ymail.com

(Received 13 February 2013; accepted 20 February 2013; online 28 February 2013)

In the title compound, C₂₀H₁₇N₃O₄, the central pyran ring adopts a boat conformation with the O atom and diagonally opposite C atoms displaced by 0.1171 (1) and 0.1791 (1) Å, respectively, from the mean plane defined by the other four atoms. The coplanar atoms of the pyran ring and the methoxybenzene ring are nearly perpendicular, as evidenced by the dihedral angle 87.01 (1)°. The amine H atom forms an intramolecular N—H⋯O(nitro) hydrogen bond. In the crystal, molecules are linked into dimeric aggregates by N—H⋯O(nitro) hydrogen bonds, generating an R₂²(12) graph-set motif.

Related literature

For background to compounds containing the 4H-pyran unit, see: Brahmachari (2010 ); Hatakeyama et al. (1988 ). For 2-amino-4H-pyrans as photoactive materials, see: Armetso et al. (1989 ). For graph-set motifs, see: Bernstein et al. (1995 ). For ring conformation analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₀H₁₇N₃O₄
M_r = 363.37
Monoclinic, C 2/c
a = 22.9422 (10) Å
b = 7.5828 (3) Å
c = 22.7319 (10) Å
β = 112.576 (2)°
V = 3651.5 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.23 × 0.21 × 0.19 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.967, T_max = 0.974
15550 measured reflections
4003 independent reflections
2915 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.116
S = 1.05
4003 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.86	2.00	2.6203 (19)	128
N2—H2⋯O2ⁱ	0.86	2.26	3.0114 (18)	147
Symmetry code: (i) -x, -y, -z.

Data collection: APEX2 (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: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813004923/tk5197sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813004923/tk5197Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813004923/tk5197Isup3.cml

checkCIF report

Comment top

4H-Pyran units constitute structural features of a broad range of bioactive natural products (Brahmachari, 2010; Hatakeyama et al., 1988). 2-Amino-4H-pyrans have also been found to be useful as photoactive materials (Armetso et al., 1989). Hence, investigation of the structural features of biologically relevant tetrahydrobenzo[b]pyran derivatives is of both scientific and practical interest. In continuation of our efforts to develop useful synthetic protocols for biologically significant molecules, we herein report an efficient and environmentally benign synthesis and the crystal structure of the title compound.

In the title compound, Fig. 1, the six-membered central pyran ring adopts a boat conformation as evidenced by the puckering parameters q₂ = 0.1713 (16) Å, θ = 98.1 (5)°, ϕ = 3.5 (6)° (Cremer & Pople, 1975). The dihedral angle between the methoxybenzene ring and the flat part of the pyran ring is 87.01 (1)° which means that the methoxybenzene ring is nearly perpendicular to the pyran ring. The acetonitrile group is almost coplanar with the plane of the pyrazole ring [the N3—C21—C2—C1 torsion angle is 174.04 (16) °]. The nitrile group has a typical bond length, i.e. N ≡C = 1.141 (3) Å. The dihedral angle between the flat part of the pyran ring and the phenyl ring is 38.62 (2)°. The phenyl ring is attached to the pyran ring by an (-)-syn-clinal conformation with torsion angle C12—C11—C1—C2 of -41.54 (3)°. Similarly, the methoxybenzene ring is attached to the pyran ring by a torsion angle C4—C3—C31—C36 of -59.51 (2)°, again indicating an (-)-syn-clinal conformation. The nitro group is attached to pyran ring at C4 with the torsion angle (C5—C4—N1—O2) of -4.89 (3)°, indicating an (-)-syn-periplanar conformation.

In the crystal structure, N2—H2···O2 hydrogen bonds link molecules into dimeric pairs, Table 1. Each of these pairs generate a graph set motif of R₂²(12) (Bernstein et al., 1995), Fig. 2. In addition, there is a N—H···O intramolecular interaction which stabilizes the structure.

Related literature top

For background to compounds containing the 4H-pyran unit, see: Brahmachari (2010); Hatakeyama et al. (1988). For 2-amino-4H-pyrans as photoactive materials, see: Armetso et al. (1989). For graph-set motifs, see: Bernstein et al. (1995). For ring conformation analysis, see: Cremer & Pople (1975).

Experimental top

A mixture of benzoylacetonitrile (1.0 mmol), 4-methoxy aldehyde (1.0 mmol), Et₃N (1.0 mmol) and EtOH (10 ml) were taken in 50 ml round bottom flask. The reaction mixture was stirred at room temperature for 5–10 min. Then N-methyl-1-(methylthio)-2-nitroethenamine was added into the reaction mixture followed by refluxing at 353 K. The consumption of starting material was monitored by TLC. After 90 min, the solid product was filtered and washed with diethyl ether (5 ml) and dried under vacuum in 92% yield; M.pt: 481 K.

Computing details top

Data collection: APEX2 (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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Partial packing diagram showing N—H···O interactions as dashed lines.

4-(4-Methoxyphenyl)-6-methylamino-5-nitro-2-phenyl-4H-pyran-3-carbonitrile top

Crystal data top

C₂₀H₁₇N₃O₄	F(000) = 1520
M_r = 363.37	D_x = 1.322 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2000 reflections
a = 22.9422 (10) Å	θ = 2–31°
b = 7.5828 (3) Å	µ = 0.09 mm⁻¹
c = 22.7319 (10) Å	T = 293 K
β = 112.576 (2)°	Block, colourless
V = 3651.5 (3) Å³	0.23 × 0.21 × 0.19 mm
Z = 8

Data collection top

Bruker Kappa APEXII diffractometer	4003 independent reflections
Radiation source: fine-focus sealed tube	2915 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 0 pixels mm^-1	θ_max = 27.0°, θ_min = 1.9°
ω and ϕ scans	h = −29→19
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→9
T_min = 0.967, T_max = 0.974	l = −25→29
15550 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0488P)² + 2.0393P] where P = (F_o² + 2F_c²)/3
4003 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₀H₁₇N₃O₄	V = 3651.5 (3) Å³
M_r = 363.37	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.9422 (10) Å	µ = 0.09 mm⁻¹
b = 7.5828 (3) Å	T = 293 K
c = 22.7319 (10) Å	0.23 × 0.21 × 0.19 mm
β = 112.576 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	4003 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2915 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.974	R_int = 0.028
15550 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.05	Δρ_max = 0.23 e Å⁻³
4003 reflections	Δρ_min = −0.18 e Å⁻³
246 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.

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	−0.07195 (5)	0.42117 (14)	0.09142 (5)	0.0433 (3)
O2	0.03608 (6)	0.15716 (16)	0.01309 (6)	0.0568 (3)
O3	0.10675 (6)	0.36536 (17)	0.04434 (6)	0.0552 (3)
O4	0.26059 (5)	0.44513 (17)	0.34242 (5)	0.0557 (3)
N1	0.05627 (6)	0.29947 (18)	0.04218 (6)	0.0430 (3)
N2	−0.06629 (7)	0.18295 (18)	0.03754 (6)	0.0469 (3)
H2	−0.0477	0.1171	0.0193	0.056*
N3	0.03447 (8)	0.9733 (2)	0.15792 (8)	0.0609 (4)
C1	−0.05459 (7)	0.59078 (19)	0.11380 (7)	0.0368 (3)
C2	0.00202 (7)	0.65426 (19)	0.12158 (6)	0.0365 (3)
C3	0.05189 (7)	0.54950 (19)	0.10871 (7)	0.0375 (3)
H3	0.0666	0.6217	0.0814	0.045*
C4	0.02191 (7)	0.38689 (19)	0.07184 (7)	0.0373 (3)
C5	−0.03688 (7)	0.3264 (2)	0.06585 (6)	0.0380 (3)
C6	−0.12770 (10)	0.1270 (3)	0.03463 (11)	0.0686 (6)
H6A	−0.1358	0.0086	0.0185	0.103*
H6B	−0.1596	0.2042	0.0069	0.103*
H6C	−0.1285	0.1310	0.0765	0.103*
C11	−0.10683 (7)	0.6820 (2)	0.12361 (7)	0.0389 (3)
C12	−0.09563 (8)	0.7928 (2)	0.17560 (8)	0.0488 (4)
H12	−0.0549	0.8048	0.2062	0.059*
C13	−0.14469 (9)	0.8848 (3)	0.18185 (9)	0.0588 (5)
H13	−0.1370	0.9592	0.2166	0.071*
C14	−0.20481 (10)	0.8673 (3)	0.13714 (9)	0.0629 (5)
H14	−0.2376	0.9317	0.1411	0.075*
C15	−0.21673 (8)	0.7544 (3)	0.08635 (8)	0.0591 (5)
H15	−0.2577	0.7407	0.0566	0.071*
C16	−0.16784 (8)	0.6615 (2)	0.07965 (7)	0.0477 (4)
H16	−0.1760	0.5849	0.0454	0.057*
C21	0.01831 (7)	0.8329 (2)	0.14170 (7)	0.0421 (4)
C31	0.10863 (7)	0.51449 (19)	0.17036 (7)	0.0367 (3)
C32	0.16598 (7)	0.5910 (2)	0.17986 (8)	0.0433 (4)
H32	0.1700	0.6576	0.1473	0.052*
C33	0.21774 (7)	0.5718 (2)	0.23641 (8)	0.0469 (4)
H33	0.2559	0.6256	0.2418	0.056*
C34	0.21227 (7)	0.4722 (2)	0.28475 (7)	0.0422 (4)
C35	0.15538 (8)	0.3913 (2)	0.27582 (7)	0.0461 (4)
H35	0.1517	0.3225	0.3081	0.055*
C36	0.10402 (7)	0.4126 (2)	0.21914 (7)	0.0438 (4)
H36	0.0660	0.3581	0.2136	0.053*
C37	0.31860 (9)	0.5346 (3)	0.35284 (10)	0.0708 (6)
H37A	0.3487	0.5077	0.3948	0.106*
H37B	0.3113	0.6595	0.3490	0.106*
H37C	0.3347	0.4966	0.3217	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0501 (6)	0.0368 (6)	0.0491 (6)	−0.0021 (5)	0.0259 (5)	−0.0061 (5)
O2	0.0772 (9)	0.0453 (7)	0.0536 (7)	0.0048 (6)	0.0315 (6)	−0.0136 (6)
O3	0.0542 (7)	0.0649 (8)	0.0549 (7)	0.0049 (6)	0.0303 (6)	−0.0050 (6)
O4	0.0465 (7)	0.0642 (8)	0.0476 (6)	0.0033 (6)	0.0085 (5)	−0.0063 (6)
N1	0.0529 (8)	0.0424 (8)	0.0351 (6)	0.0088 (6)	0.0184 (6)	0.0007 (6)
N2	0.0588 (9)	0.0369 (7)	0.0464 (7)	−0.0034 (6)	0.0219 (6)	−0.0069 (6)
N3	0.0631 (10)	0.0444 (9)	0.0710 (10)	−0.0037 (8)	0.0209 (8)	−0.0091 (8)
C1	0.0447 (8)	0.0340 (8)	0.0321 (7)	0.0022 (7)	0.0153 (6)	−0.0003 (6)
C2	0.0422 (8)	0.0328 (8)	0.0339 (7)	0.0038 (6)	0.0138 (6)	0.0000 (6)
C3	0.0427 (8)	0.0352 (8)	0.0383 (7)	0.0017 (6)	0.0198 (6)	0.0017 (6)
C4	0.0457 (9)	0.0345 (8)	0.0334 (7)	0.0063 (7)	0.0173 (6)	−0.0008 (6)
C5	0.0502 (9)	0.0322 (8)	0.0324 (7)	0.0049 (7)	0.0167 (6)	0.0014 (6)
C6	0.0754 (14)	0.0569 (12)	0.0797 (13)	−0.0223 (10)	0.0367 (11)	−0.0171 (10)
C11	0.0438 (9)	0.0399 (8)	0.0369 (7)	0.0038 (7)	0.0197 (6)	0.0036 (6)
C12	0.0538 (10)	0.0542 (10)	0.0419 (8)	0.0036 (8)	0.0224 (7)	−0.0048 (7)
C13	0.0724 (13)	0.0603 (12)	0.0570 (10)	0.0090 (10)	0.0396 (10)	−0.0056 (9)
C14	0.0657 (12)	0.0717 (13)	0.0672 (12)	0.0216 (10)	0.0431 (10)	0.0088 (10)
C15	0.0468 (10)	0.0821 (14)	0.0525 (10)	0.0111 (9)	0.0235 (8)	0.0098 (10)
C16	0.0478 (9)	0.0574 (10)	0.0407 (8)	0.0031 (8)	0.0200 (7)	−0.0001 (7)
C21	0.0414 (8)	0.0419 (9)	0.0416 (8)	0.0046 (7)	0.0143 (7)	−0.0002 (7)
C31	0.0409 (8)	0.0323 (8)	0.0394 (7)	0.0032 (6)	0.0182 (6)	−0.0037 (6)
C32	0.0443 (9)	0.0421 (9)	0.0483 (8)	−0.0010 (7)	0.0232 (7)	0.0010 (7)
C33	0.0404 (9)	0.0464 (10)	0.0557 (9)	−0.0053 (7)	0.0203 (7)	−0.0052 (8)
C34	0.0411 (8)	0.0397 (9)	0.0434 (8)	0.0050 (7)	0.0136 (7)	−0.0087 (7)
C35	0.0517 (10)	0.0457 (9)	0.0420 (8)	−0.0007 (8)	0.0192 (7)	0.0042 (7)
C36	0.0414 (9)	0.0447 (9)	0.0470 (9)	−0.0054 (7)	0.0190 (7)	0.0019 (7)
C37	0.0469 (11)	0.0847 (15)	0.0647 (12)	−0.0051 (10)	0.0034 (9)	−0.0130 (11)

Geometric parameters (Å, º) top

O1—C5	1.3641 (18)	C11—C12	1.391 (2)
O1—C1	1.3842 (18)	C12—C13	1.377 (2)
O2—N1	1.2573 (17)	C12—H12	0.9300
O3—N1	1.2448 (17)	C13—C14	1.370 (3)
O4—C34	1.3688 (19)	C13—H13	0.9300
O4—C37	1.430 (2)	C14—C15	1.378 (3)
N1—C4	1.3868 (18)	C14—H14	0.9300
N2—C5	1.311 (2)	C15—C16	1.382 (2)
N2—C6	1.448 (2)	C15—H15	0.9300
N2—H2	0.8602	C16—H16	0.9300
N3—C21	1.141 (2)	C31—C32	1.377 (2)
C1—C2	1.332 (2)	C31—C36	1.388 (2)
C1—C11	1.473 (2)	C32—C33	1.383 (2)
C2—C21	1.432 (2)	C32—H32	0.9300
C2—C3	1.511 (2)	C33—C34	1.378 (2)
C3—C4	1.501 (2)	C33—H33	0.9300
C3—C31	1.526 (2)	C34—C35	1.385 (2)
C3—H3	0.9800	C35—C36	1.382 (2)
C4—C5	1.381 (2)	C35—H35	0.9300
C6—H6A	0.9600	C36—H36	0.9300
C6—H6B	0.9600	C37—H37A	0.9600
C6—H6C	0.9600	C37—H37B	0.9600
C11—C16	1.381 (2)	C37—H37C	0.9600

C5—O1—C1	120.81 (12)	C14—C13—C12	120.29 (17)
C34—O4—C37	116.60 (15)	C14—C13—H13	119.9
O3—N1—O2	120.97 (13)	C12—C13—H13	119.9
O3—N1—C4	118.86 (13)	C13—C14—C15	120.09 (16)
O2—N1—C4	120.17 (14)	C13—C14—H14	120.0
C5—N2—C6	125.02 (15)	C15—C14—H14	120.0
C5—N2—H2	117.5	C14—C15—C16	120.06 (17)
C6—N2—H2	117.5	C14—C15—H15	120.0
C2—C1—O1	120.88 (13)	C16—C15—H15	120.0
C2—C1—C11	128.23 (14)	C11—C16—C15	120.19 (16)
O1—C1—C11	110.85 (12)	C11—C16—H16	119.9
C1—C2—C21	120.38 (14)	C15—C16—H16	119.9
C1—C2—C3	123.82 (13)	N3—C21—C2	176.34 (17)
C21—C2—C3	115.77 (13)	C32—C31—C36	118.06 (14)
C4—C3—C2	108.74 (12)	C32—C31—C3	119.84 (13)
C4—C3—C31	114.61 (12)	C36—C31—C3	122.05 (13)
C2—C3—C31	110.87 (11)	C31—C32—C33	121.95 (15)
C4—C3—H3	107.4	C31—C32—H32	119.0
C2—C3—H3	107.4	C33—C32—H32	119.0
C31—C3—H3	107.4	C34—C33—C32	119.37 (15)
C5—C4—N1	120.62 (14)	C34—C33—H33	120.3
C5—C4—C3	123.27 (13)	C32—C33—H33	120.3
N1—C4—C3	116.10 (13)	O4—C34—C33	123.88 (15)
N2—C5—O1	111.68 (14)	O4—C34—C35	116.45 (15)
N2—C5—C4	128.53 (14)	C33—C34—C35	119.67 (14)
O1—C5—C4	119.79 (13)	C36—C35—C34	120.22 (15)
N2—C6—H6A	109.5	C36—C35—H35	119.9
N2—C6—H6B	109.5	C34—C35—H35	119.9
H6A—C6—H6B	109.5	C35—C36—C31	120.72 (15)
N2—C6—H6C	109.5	C35—C36—H36	119.6
H6A—C6—H6C	109.5	C31—C36—H36	119.6
H6B—C6—H6C	109.5	O4—C37—H37A	109.5
C16—C11—C12	119.20 (14)	O4—C37—H37B	109.5
C16—C11—C1	119.67 (14)	H37A—C37—H37B	109.5
C12—C11—C1	121.10 (14)	O4—C37—H37C	109.5
C13—C12—C11	120.12 (16)	H37A—C37—H37C	109.5
C13—C12—H12	119.9	H37B—C37—H37C	109.5
C11—C12—H12	119.9

C5—O1—C1—C2	−12.1 (2)	C2—C1—C11—C12	−41.5 (2)
C5—O1—C1—C11	165.46 (12)	O1—C1—C11—C12	141.09 (14)
O1—C1—C2—C21	176.84 (13)	C16—C11—C12—C13	−2.0 (2)
C11—C1—C2—C21	−0.3 (2)	C1—C11—C12—C13	176.20 (15)
O1—C1—C2—C3	−1.5 (2)	C11—C12—C13—C14	0.3 (3)
C11—C1—C2—C3	−178.63 (13)	C12—C13—C14—C15	1.4 (3)
C1—C2—C3—C4	13.69 (19)	C13—C14—C15—C16	−1.4 (3)
C21—C2—C3—C4	−164.72 (12)	C12—C11—C16—C15	2.0 (2)
C1—C2—C3—C31	−113.18 (15)	C1—C11—C16—C15	−176.22 (15)
C21—C2—C3—C31	68.41 (16)	C14—C15—C16—C11	−0.3 (3)
O3—N1—C4—C5	174.32 (13)	C1—C2—C21—N3	174 (100)
O2—N1—C4—C5	−4.9 (2)	C3—C2—C21—N3	−7 (3)
O3—N1—C4—C3	−4.48 (19)	C4—C3—C31—C32	123.21 (15)
O2—N1—C4—C3	176.31 (12)	C2—C3—C31—C32	−113.23 (15)
C2—C3—C4—C5	−14.61 (19)	C4—C3—C31—C36	−59.51 (18)
C31—C3—C4—C5	110.08 (16)	C2—C3—C31—C36	64.05 (18)
C2—C3—C4—N1	164.15 (12)	C36—C31—C32—C33	−1.3 (2)
C31—C3—C4—N1	−71.16 (16)	C3—C31—C32—C33	176.07 (14)
C6—N2—C5—O1	−1.5 (2)	C31—C32—C33—C34	0.5 (2)
C6—N2—C5—C4	178.56 (17)	C37—O4—C34—C33	3.3 (2)
C1—O1—C5—N2	−168.93 (12)	C37—O4—C34—C35	−177.38 (15)
C1—O1—C5—C4	11.0 (2)	C32—C33—C34—O4	180.00 (14)
N1—C4—C5—N2	4.7 (2)	C32—C33—C34—C35	0.7 (2)
C3—C4—C5—N2	−176.58 (14)	O4—C34—C35—C36	179.60 (14)
N1—C4—C5—O1	−175.20 (12)	C33—C34—C35—C36	−1.0 (2)
C3—C4—C5—O1	3.5 (2)	C34—C35—C36—C31	0.2 (2)
C2—C1—C11—C16	136.64 (17)	C32—C31—C36—C35	1.0 (2)
O1—C1—C11—C16	−40.72 (18)	C3—C31—C36—C35	−176.37 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	2.00	2.6203 (19)	128
N2—H2···O2ⁱ	0.86	2.26	3.0114 (18)	147

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇N₃O₄
M_r	363.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	22.9422 (10), 7.5828 (3), 22.7319 (10)
β (°)	112.576 (2)
V (Å³)	3651.5 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.23 × 0.21 × 0.19

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.967, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	15550, 4003, 2915
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.116, 1.05
No. of reflections	4003
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	2.00	2.6203 (19)	128
N2—H2···O2ⁱ	0.86	2.26	3.0114 (18)	147

Symmetry code: (i) −x, −y, −z.

Acknowledgements

JS thanks the UGC for the FIST support. JS and RV thank the management of Madura College for their encouragement and support. RRK thanks the DST, NewDelhi, for funds under the fast-track scheme (No·SR/FT/CS-073/2009).

References

Armetso, D., Horspool, W. M., Martin, N., Ramos, A. & Seoane, C. (1989). J. Org. Chem. 54, 3069–3072. Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Brahmachari, G. (2010). In Handbook of Pharmaceutical Natural Products. Weinheim: Wiley-VCH Verlag GmbH & Co. Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Hatakeyama, S., Ochi, N., Numata, H. & Takano, S. (1988). J. Chem. Soc. Chem. Commun. pp. 1202–1204. CrossRef Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 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

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-(4-Meth­­oxy­phen­yl)-6-methyl­amino-5-nitro-2-phenyl-4H-pyran-3-carbo­nitrile

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-(4-Methoxyphenyl)-6-methylamino-5-nitro-2-phenyl-4H-pyran-3-carbonitrile