[1-(3-Nitro­phen­yl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazin-3-ylidine]malonaldehyde

NizamMohideen, M.; SubbiahPandi, A.; Selvam, N.P.; Perumal, P.T.; Damodiran, M.

doi:10.1107/S1600536809006023

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o582

doi:10.1107/S1600536809006023

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[1-(3-Nitrophenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazin-3-ylidine]malonaldehyde

M. NizamMohideen,^a A. SubbiahPandi,^b ^* N. Panneer Selvam,^c P. T. Perumal ^c and M. Damodiran ^c

^aDepartment of Physics, The New College (Autonomous), Chennai 600 014, India, ^bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^cOrganic Chemistry Division, Central Leather Research Institute, Chennai 600 020, India
^*Correspondence e-mail: a_spandian@yahoo.com

(Received 17 February 2009; accepted 19 February 2009; online 25 February 2009)

The oxazine ring in the title compound, C₂₁H₁₄N₂O₅, adopts a flattened boat conformation. The nitrophenyl ring and the naphthalene ring system enclose a dihedral angle of 89.2 (1)°. An intramolecular hydrogen bond is formed between the NH group and one of the adjacent carbonyl O atoms. In addition, the NH group forms an intermolecular hydrogen bond to a symmetry equivalent of this carbonyl O atom, connecting the molecules into centrosymmetric dimers. The structure also contains C—H⋯O intermolecular interactions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For ring puckering parameters, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₁H₁₄N₂O₅
M_r = 374.34
Monoclinic, P 2₁ /n
a = 7.9191 (4) Å
b = 23.3876 (11) Å
c = 9.6199 (5) Å
β = 104.632 (2)°
V = 1723.91 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.33 × 0.27 × 0.25 mm

Data collection

'Bruker Kappa APEXII CCD diffractometer'
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.897, T_max = 0.974
16263 measured reflections
3023 independent reflections
2334 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.102
S = 1.00
3023 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.12 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
C11—H11⋯O3ⁱ	0.93	2.54	3.395 (2)	153
C18—H18⋯O4ⁱⁱ	0.93	2.44	3.259 (2)	148
N1—H1⋯O4ⁱⁱ	0.86	2.36	3.078 (2)	141
N1—H1⋯O4	0.86	2.02	2.670 (2)	132
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y, -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: 10.1107/S1600536809006023/bt2875sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006023/bt2875Isup2.hkl

checkCIF report

Comment top

A view of the title compound with the atom-numbering scheme is shown in Fig. 1. The bond lengths C1—O1 and C1—N1 in the oxazine ring are 1.344 (2) and 1.307 (2)Å respectively.

The six membered oxazine moiety is not planar, having a total puckering amplitude, Q_T of 0.329 (2) Å and adopting a boat conformation [θ = 81.8 (1) and ϕ = 171.8 (2)°] (Cremer & Pople, 1975), and the lowest displacement asymmetry parameters Δ_S(O1) is 8.0 (1)° (Nardelli, 1983). The dihedral angle between the naphthalene and benzene ring is 89.2 (1)°.

The crystal structure of the title compound is characterized by bifurcated hydrogen bonds between the amine and aldehyde groups (Table 1 and Fig. 2). One interaction is an intramolecular N—H···O hydrogen bond between donor atom N1 and acceptor atom O4, described by the graph-set motif S(6) (Bernstein et al., 1995). Atom N1 in the molecule at (x, y, z) also acts as a hydrogen-bond donor via atom H1 to atom O4 in the molecule at (1 - x, -y, -z). This intermolecular hydrogen bond links the molecules into dimers described by a graph-set motif R²₂(12). The structure also contains C—H···O intermolecular interactions. Atom C11 and C18 in the molecule at (x, y, z) acts as a hydrogen-bond donor via atom H11 and H18 to atom O3 and O4 in the molecule at (2 - x, -y, 1 - z). This intermolecular hydrogen bond links the molecules into dimers with a cyclic R²₂(20) and R²₂(18) ring system, respectively.

Related literature top

For hydrogen-bond motifs, see: Bernstein et al. (1995). Fo ring puckering parameters, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

To the solution containing N-[(3-Nitro-phenyl)-(2-hydroxy-napthalen-1-yl) -methyl]-acetamide (10 mmol) dissolved in DMF (12 equiv), POCl3 (8 eqiuv) was added slowly dropwise (around 15 min) at 273°K, then the reaction mixture was allowed to reach room temperature. The reaction mixture was stirred at 363°K for about 3.5 h. Afer completion of the reaction, it was allowed to cool to room temperature. Then it was poured into crushed ice and refrigerated overnight. The solution was neutralized with sodium acetate and the crude compound was extracted with dichloromethane (3 × 50 ml) and washed with water (3 × 25 ml). Organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified through column chromatography using ethyl acetate: petroleum ether (1:1) as eluent. Single crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a solution in Ethanol.

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. The molecular structure of (I), showing the atom-numbering scheme for (I). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of compound (I), showing the R²₂(12), R²₂(20) and R²₂(18) rings. Hydrogen bonding is shown as dashed lines. H atoms not involved in the hydrogen bonding have been omitted for clarity. [Symmetry codes: (*)-x + 2, -y, -z + 1, ($)-x + 1, -y, -z]

[1-(3-Nitrophenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazin-3- ylidine]malonaldehyde top

Crystal data top

C₂₁H₁₄N₂O₅	F(000) = 776
M_r = 374.34	D_x = 1.442 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2334 reflections
a = 7.9191 (4) Å	θ = 2.5–25°
b = 23.3876 (11) Å	µ = 0.11 mm⁻¹
c = 9.6199 (5) Å	T = 293 K
β = 104.632 (2)°	Block, colourless
V = 1723.91 (15) Å³	0.33 × 0.27 × 0.25 mm
Z = 4

Data collection top

'Bruker Kappa APEXII CCD diffractometer'	3023 independent reflections
Radiation source: fine-focus sealed tube	2334 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω and ϕ scan	θ_max = 24.9°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
T_min = 0.897, T_max = 0.974	k = −27→27
16263 measured reflections	l = −11→11

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0509P)² + 0.352P] where P = (F_o² + 2F_c²)/3
3023 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₁H₁₄N₂O₅	V = 1723.91 (15) Å³
M_r = 374.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.9191 (4) Å	µ = 0.11 mm⁻¹
b = 23.3876 (11) Å	T = 293 K
c = 9.6199 (5) Å	0.33 × 0.27 × 0.25 mm
β = 104.632 (2)°

Data collection top

'Bruker Kappa APEXII CCD diffractometer'	3023 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2334 reflections with I > 2σ(I)
T_min = 0.897, T_max = 0.974	R_int = 0.032
16263 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.00	Δρ_max = 0.12 e Å⁻³
3023 reflections	Δρ_min = −0.17 e Å⁻³
253 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	0.30114 (13)	0.16841 (5)	0.13932 (12)	0.0486 (3)
O2	0.8553 (2)	−0.07387 (6)	0.43720 (18)	0.0878 (5)
O3	0.8486 (3)	−0.07086 (8)	0.6565 (2)	0.1195 (7)
O4	0.30819 (17)	0.00916 (5)	−0.05620 (14)	0.0638 (4)
O5	−0.14205 (16)	0.09772 (6)	−0.06754 (16)	0.0718 (4)
N1	0.47317 (16)	0.09268 (5)	0.11444 (13)	0.0418 (3)
H1	0.4847	0.0619	0.0690	0.050*
N2	0.8208 (2)	−0.04987 (7)	0.53794 (19)	0.0637 (4)
C1	0.3180 (2)	0.11583 (6)	0.08808 (16)	0.0401 (4)
C2	0.62913 (19)	0.11553 (6)	0.21612 (16)	0.0388 (4)
H2	0.7310	0.1063	0.1799	0.047*
C3	0.61165 (19)	0.17956 (6)	0.21877 (16)	0.0395 (4)
C4	0.45014 (19)	0.20287 (6)	0.18043 (17)	0.0412 (4)
C5	0.4178 (2)	0.26167 (7)	0.17688 (17)	0.0464 (4)
H5	0.3042	0.2757	0.1503	0.056*
C6	0.5556 (2)	0.29776 (7)	0.21305 (18)	0.0485 (4)
H6	0.5363	0.3370	0.2088	0.058*
C7	0.7285 (2)	0.27682 (7)	0.25716 (17)	0.0439 (4)
C8	0.8737 (2)	0.31383 (8)	0.29883 (19)	0.0529 (4)
H8	0.8562	0.3532	0.2938	0.063*
C9	1.0376 (2)	0.29305 (8)	0.3459 (2)	0.0576 (5)
H9	1.1313	0.3181	0.3739	0.069*
C10	1.0666 (2)	0.23391 (8)	0.35255 (19)	0.0555 (5)
H10	1.1796	0.2199	0.3856	0.067*
C11	0.9305 (2)	0.19657 (7)	0.31089 (17)	0.0474 (4)
H11	0.9518	0.1574	0.3150	0.057*
C12	0.7579 (2)	0.21687 (7)	0.26167 (16)	0.0402 (4)
C13	0.65335 (18)	0.08758 (6)	0.36265 (16)	0.0370 (3)
C14	0.6049 (2)	0.11392 (7)	0.47526 (18)	0.0504 (4)
H14	0.5557	0.1503	0.4621	0.061*
C15	0.6281 (2)	0.08734 (8)	0.60702 (19)	0.0590 (5)
H15	0.5947	0.1060	0.6812	0.071*
C16	0.6998 (2)	0.03369 (8)	0.62976 (18)	0.0510 (4)
H16	0.7172	0.0157	0.7184	0.061*
C17	0.7447 (2)	0.00769 (7)	0.51666 (18)	0.0441 (4)
C18	0.72429 (19)	0.03325 (7)	0.38466 (17)	0.0410 (4)
H18	0.7578	0.0142	0.3110	0.049*
C19	0.1647 (2)	0.08978 (7)	0.00800 (16)	0.0425 (4)
C20	−0.0008 (2)	0.11766 (8)	−0.00797 (18)	0.0525 (4)
H20	0.0004	0.1542	0.0307	0.063*
C21	0.1741 (2)	0.03622 (8)	−0.05856 (18)	0.0529 (4)
H21	0.0691	0.0200	−0.1087	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0428 (6)	0.0418 (7)	0.0611 (7)	−0.0005 (5)	0.0128 (5)	−0.0115 (5)
O2	0.1298 (13)	0.0574 (9)	0.0767 (11)	0.0390 (9)	0.0270 (10)	0.0026 (8)
O3	0.1869 (19)	0.1002 (13)	0.0839 (12)	0.0799 (13)	0.0572 (12)	0.0540 (10)
O4	0.0610 (8)	0.0556 (8)	0.0703 (9)	0.0025 (6)	0.0082 (6)	−0.0219 (6)
O5	0.0463 (7)	0.0827 (10)	0.0801 (10)	−0.0028 (7)	0.0041 (7)	−0.0112 (8)
N1	0.0474 (8)	0.0357 (7)	0.0391 (7)	0.0028 (6)	0.0050 (6)	−0.0071 (6)
N2	0.0758 (10)	0.0516 (9)	0.0642 (11)	0.0201 (8)	0.0189 (8)	0.0122 (8)
C1	0.0477 (9)	0.0381 (9)	0.0355 (8)	0.0008 (7)	0.0123 (7)	−0.0007 (7)
C2	0.0400 (8)	0.0348 (8)	0.0408 (9)	0.0007 (6)	0.0089 (7)	−0.0045 (7)
C3	0.0466 (9)	0.0352 (8)	0.0369 (8)	0.0012 (7)	0.0111 (7)	−0.0008 (7)
C4	0.0447 (9)	0.0375 (9)	0.0419 (9)	−0.0009 (7)	0.0116 (7)	−0.0032 (7)
C5	0.0504 (9)	0.0402 (9)	0.0490 (10)	0.0084 (8)	0.0134 (8)	−0.0002 (7)
C6	0.0645 (11)	0.0330 (9)	0.0511 (10)	0.0038 (8)	0.0202 (8)	0.0013 (7)
C7	0.0582 (10)	0.0380 (9)	0.0392 (9)	−0.0041 (7)	0.0191 (7)	−0.0002 (7)
C8	0.0672 (12)	0.0434 (10)	0.0530 (11)	−0.0129 (9)	0.0245 (9)	−0.0026 (8)
C9	0.0598 (11)	0.0612 (12)	0.0553 (11)	−0.0230 (9)	0.0211 (9)	−0.0057 (9)
C10	0.0486 (10)	0.0660 (12)	0.0531 (11)	−0.0078 (9)	0.0150 (8)	−0.0017 (9)
C11	0.0491 (9)	0.0467 (10)	0.0470 (10)	−0.0016 (8)	0.0133 (8)	0.0000 (8)
C12	0.0482 (9)	0.0386 (9)	0.0354 (8)	−0.0028 (7)	0.0136 (7)	−0.0010 (7)
C13	0.0338 (7)	0.0342 (8)	0.0404 (8)	−0.0017 (6)	0.0044 (6)	−0.0046 (7)
C14	0.0612 (11)	0.0413 (10)	0.0485 (10)	0.0106 (8)	0.0133 (8)	−0.0042 (8)
C15	0.0745 (12)	0.0609 (12)	0.0441 (11)	0.0126 (10)	0.0197 (9)	−0.0063 (9)
C16	0.0554 (10)	0.0559 (11)	0.0391 (9)	0.0020 (8)	0.0071 (7)	0.0031 (8)
C17	0.0431 (9)	0.0396 (9)	0.0466 (10)	0.0042 (7)	0.0056 (7)	0.0025 (7)
C18	0.0415 (8)	0.0389 (9)	0.0417 (9)	0.0028 (7)	0.0088 (7)	−0.0055 (7)
C19	0.0448 (9)	0.0458 (10)	0.0362 (8)	−0.0034 (7)	0.0087 (7)	−0.0027 (7)
C20	0.0488 (10)	0.0591 (11)	0.0482 (10)	−0.0017 (8)	0.0094 (8)	−0.0038 (8)
C21	0.0511 (10)	0.0563 (11)	0.0482 (10)	−0.0069 (9)	0.0068 (8)	−0.0092 (8)

Geometric parameters (Å, º) top

O1—C1	1.3440 (18)	C8—C9	1.352 (3)
O1—C4	1.4009 (18)	C8—H8	0.9300
O2—N2	1.209 (2)	C9—C10	1.401 (3)
O3—N2	1.210 (2)	C9—H9	0.9300
O4—C21	1.232 (2)	C10—C11	1.366 (2)
O5—C20	1.214 (2)	C10—H10	0.9300
N1—C1	1.3075 (19)	C11—C12	1.411 (2)
N1—C2	1.4689 (19)	C11—H11	0.9300
N1—H1	0.8600	C13—C14	1.382 (2)
N2—C17	1.468 (2)	C13—C18	1.384 (2)
C1—C19	1.402 (2)	C14—C15	1.382 (3)
C2—C3	1.505 (2)	C14—H14	0.9300
C2—C13	1.521 (2)	C15—C16	1.372 (2)
C2—H2	0.9800	C15—H15	0.9300
C3—C4	1.353 (2)	C16—C17	1.370 (2)
C3—C12	1.425 (2)	C16—H16	0.9300
C4—C5	1.398 (2)	C17—C18	1.376 (2)
C5—C6	1.354 (2)	C18—H18	0.9300
C5—H5	0.9300	C19—C21	1.417 (2)
C6—C7	1.414 (2)	C19—C20	1.437 (2)
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.414 (2)	C21—H21	0.9300
C7—C12	1.420 (2)

C1—O1—C4	118.37 (12)	C11—C10—C9	120.65 (17)
C1—N1—C2	124.71 (13)	C11—C10—H10	119.7
C1—N1—H1	117.6	C9—C10—H10	119.7
C2—N1—H1	117.6	C10—C11—C12	120.58 (16)
O2—N2—O3	122.89 (17)	C10—C11—H11	119.7
O2—N2—C17	118.80 (16)	C12—C11—H11	119.7
O3—N2—C17	118.31 (17)	C11—C12—C7	118.71 (14)
N1—C1—O1	118.90 (14)	C11—C12—C3	122.58 (14)
N1—C1—C19	124.59 (14)	C7—C12—C3	118.70 (14)
O1—C1—C19	116.51 (13)	C14—C13—C18	118.15 (15)
N1—C2—C3	107.93 (12)	C14—C13—C2	122.67 (14)
N1—C2—C13	110.41 (12)	C18—C13—C2	119.18 (13)
C3—C2—C13	113.73 (12)	C13—C14—C15	121.30 (16)
N1—C2—H2	108.2	C13—C14—H14	119.3
C3—C2—H2	108.2	C15—C14—H14	119.3
C13—C2—H2	108.2	C16—C15—C14	120.76 (16)
C4—C3—C12	118.39 (14)	C16—C15—H15	119.6
C4—C3—C2	118.75 (13)	C14—C15—H15	119.6
C12—C3—C2	122.86 (13)	C17—C16—C15	117.36 (16)
C3—C4—O1	121.07 (13)	C17—C16—H16	121.3
C3—C4—C5	123.91 (15)	C15—C16—H16	121.3
O1—C4—C5	115.02 (13)	C16—C17—C18	123.15 (15)
C6—C5—C4	118.41 (15)	C16—C17—N2	118.43 (15)
C6—C5—H5	120.8	C18—C17—N2	118.41 (15)
C4—C5—H5	120.8	C17—C18—C13	119.26 (14)
C5—C6—C7	121.19 (15)	C17—C18—H18	120.4
C5—C6—H6	119.4	C13—C18—H18	120.4
C7—C6—H6	119.4	C1—C19—C21	119.67 (15)
C6—C7—C8	121.97 (15)	C1—C19—C20	120.10 (15)
C6—C7—C12	119.34 (15)	C21—C19—C20	120.22 (15)
C8—C7—C12	118.69 (15)	O5—C20—C19	125.67 (18)
C9—C8—C7	121.21 (17)	O5—C20—H20	117.2
C9—C8—H8	119.4	C19—C20—H20	117.2
C7—C8—H8	119.4	O4—C21—C19	126.11 (16)
C8—C9—C10	120.15 (16)	O4—C21—H21	116.9
C8—C9—H9	119.9	C19—C21—H21	116.9
C10—C9—H9	119.9

C2—N1—C1—O1	10.5 (2)	C8—C7—C12—C3	−179.59 (14)
C2—N1—C1—C19	−169.97 (14)	C4—C3—C12—C11	176.48 (15)
C4—O1—C1—N1	18.7 (2)	C2—C3—C12—C11	−2.7 (2)
C4—O1—C1—C19	−160.81 (13)	C4—C3—C12—C7	−2.3 (2)
C1—N1—C2—C3	−31.1 (2)	C2—C3—C12—C7	178.44 (14)
C1—N1—C2—C13	93.82 (17)	N1—C2—C13—C14	−100.41 (16)
N1—C2—C3—C4	24.17 (19)	C3—C2—C13—C14	21.1 (2)
C13—C2—C3—C4	−98.69 (16)	N1—C2—C13—C18	78.61 (16)
N1—C2—C3—C12	−156.62 (13)	C3—C2—C13—C18	−159.90 (13)
C13—C2—C3—C12	80.52 (17)	C18—C13—C14—C15	0.8 (2)
C12—C3—C4—O1	−179.04 (13)	C2—C13—C14—C15	179.79 (16)
C2—C3—C4—O1	0.2 (2)	C13—C14—C15—C16	−0.2 (3)
C12—C3—C4—C5	1.6 (2)	C14—C15—C16—C17	−0.8 (3)
C2—C3—C4—C5	−179.12 (15)	C15—C16—C17—C18	1.3 (3)
C1—O1—C4—C3	−24.0 (2)	C15—C16—C17—N2	−179.66 (15)
C1—O1—C4—C5	155.39 (14)	O2—N2—C17—C16	177.49 (18)
C3—C4—C5—C6	0.4 (2)	O3—N2—C17—C16	−3.6 (3)
O1—C4—C5—C6	−178.97 (14)	O2—N2—C17—C18	−3.4 (3)
C4—C5—C6—C7	−1.7 (2)	O3—N2—C17—C18	175.53 (19)
C5—C6—C7—C8	−178.35 (16)	C16—C17—C18—C13	−0.7 (2)
C5—C6—C7—C12	0.9 (2)	N2—C17—C18—C13	−179.79 (14)
C6—C7—C8—C9	177.48 (16)	C14—C13—C18—C17	−0.3 (2)
C12—C7—C8—C9	−1.8 (2)	C2—C13—C18—C17	−179.37 (13)
C7—C8—C9—C10	0.8 (3)	N1—C1—C19—C21	−4.3 (2)
C8—C9—C10—C11	0.4 (3)	O1—C1—C19—C21	175.26 (14)
C9—C10—C11—C12	−0.6 (3)	N1—C1—C19—C20	176.56 (15)
C10—C11—C12—C7	−0.4 (2)	O1—C1—C19—C20	−3.9 (2)
C10—C11—C12—C3	−179.22 (15)	C1—C19—C20—O5	−175.50 (17)
C6—C7—C12—C11	−177.72 (14)	C21—C19—C20—O5	5.3 (3)
C8—C7—C12—C11	1.5 (2)	C1—C19—C21—O4	−1.5 (3)
C6—C7—C12—C3	1.2 (2)	C20—C19—C21—O4	177.67 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O3ⁱ	0.93	2.54	3.395 (2)	153
C18—H18···O4ⁱⁱ	0.93	2.44	3.259 (2)	148
N1—H1···O4ⁱⁱ	0.86	2.36	3.078 (2)	141
N1—H1···O4	0.86	2.02	2.670 (2)	132
C20—H20···O1	0.93	2.37	2.724 (2)	102

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄N₂O₅
M_r	374.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.9191 (4), 23.3876 (11), 9.6199 (5)
β (°)	104.632 (2)
V (Å³)	1723.91 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.33 × 0.27 × 0.25

Data collection
Diffractometer	'Bruker Kappa APEXII CCD diffractometer'
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.897, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	16263, 3023, 2334
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.593

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.102, 1.00
No. of reflections	3023
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.17

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

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O3ⁱ	0.93	2.54	3.395 (2)	152.9
C18—H18···O4ⁱⁱ	0.93	2.44	3.259 (2)	147.6
N1—H1···O4ⁱⁱ	0.86	2.36	3.078 (2)	141.4
N1—H1···O4	0.86	2.02	2.670 (2)	132.0
C20—H20···O1	0.93	2.37	2.724 (2)	102.3

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

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help in collecting the X-ray intensity data. MNM and ASP thank Dr J. Jothi Kumar, Principal of Presidency College, Chennai, India, for providing the computer and internet facilities.

References

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
Bruker (2004). APEX2, SAINT, XPREP and SADABS. 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
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science 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

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Volume 65| Part 3| March 2009| Page o582

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

[1-(3-Nitro­phen­yl)-2,3-di­hydro-1H-naphtho[1,2-e][1,3]oxazin-3-ylidine]malonaldehyde

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

[1-(3-Nitrophenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazin-3-ylidine]malonaldehyde