1-Phenyl-1H-naphtho-[1,2-e][1,3]oxazin-3(2H)-one.

In the title compound, C(18)H(13)NO(2), the naphthalene (r.m.s. deviation = 0.025 Å) and benzaldehyde (r.m.s. deviation = 0.006 Å) groups are oriented at a dihedral angle of 89.48 (4)°. The oxazine group is oriented at dihedral angles of 13.36 (4) and 85.08 (5)°, respectively, with respect to the naphthalene and benzaldehyde fragments. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R(2) (2)(8) loops. The dimers are linked into [010] chains via N-H⋯O hydrogen bonds. Weak C-H⋯π links and aromatic π-π stacking between the centroids of the naphthalene phenyl rings [centroid-centroid separation = 3.5977 (8) Å] help to consolidate the packing.

Related literature

For background to oxazinones, see: Patel et al. (1999 ▶); Waxman & Darke (2000 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H13NO2

M = 275.29

Monoclinic,

a = 11.5625 (4) Å

b = 16.9228 (5) Å

c = 7.2394 (2) Å

β = 98.155 (1)°

V = 1402.21 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.32 × 0.22 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.980, T max = 0.982

9236 measured reflections

2533 independent reflections

1961 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.111

S = 1.03

2533 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035841/hb5635sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035841/hb5635Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H13NO2	F(000) = 576
Mr = 275.29	Dx = 1.304 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1961 reflections
a = 11.5625 (4) Å	θ = 2.2–25.3°
b = 16.9228 (5) Å	µ = 0.09 mm−1
c = 7.2394 (2) Å	T = 296 K
β = 98.155 (1)°	Rod, colourless
V = 1402.21 (7) Å3	0.32 × 0.22 × 0.22 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2533 independent reflections
Radiation source: fine-focus sealed tube	1961 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 2.2°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −18→20
Tmin = 0.980, Tmax = 0.982	l = −8→6
9236 measured reflections

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) = 0.111	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0535P)2 + 0.2624P] where P = (Fo2 + 2Fc2)/3
2533 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.89839 (10)	0.06939 (6)	0.83483 (14)	0.0559 (4)
O2	0.91991 (11)	0.19318 (7)	0.92712 (18)	0.0737 (5)
N1	0.85664 (10)	0.16926 (7)	0.62191 (18)	0.0510 (4)
C1	0.81409 (12)	−0.02577 (8)	0.3762 (2)	0.0436 (5)
C2	0.75736 (14)	−0.01136 (10)	0.1926 (2)	0.0563 (5)
C3	0.73596 (18)	−0.07145 (12)	0.0667 (3)	0.0715 (7)
C4	0.77142 (19)	−0.14822 (12)	0.1148 (3)	0.0767 (8)
C5	0.82829 (16)	−0.16422 (10)	0.2880 (3)	0.0656 (7)
C6	0.85044 (12)	−0.10406 (8)	0.4248 (2)	0.0488 (5)
C7	0.90596 (13)	−0.11995 (8)	0.6071 (2)	0.0523 (5)
C8	0.92163 (13)	−0.06237 (8)	0.7386 (2)	0.0502 (5)
C9	0.88322 (12)	0.01469 (8)	0.6891 (2)	0.0435 (4)
C10	0.83343 (11)	0.03472 (8)	0.51467 (19)	0.0406 (4)
C11	0.79834 (12)	0.11910 (8)	0.4725 (2)	0.0434 (4)
C12	0.66655 (12)	0.13238 (8)	0.4466 (2)	0.0459 (5)
C13	0.61359 (16)	0.18002 (12)	0.3073 (3)	0.0771 (7)
C14	0.49394 (18)	0.19161 (15)	0.2832 (3)	0.0978 (9)
C15	0.42673 (16)	0.15621 (12)	0.3962 (3)	0.0782 (7)
C16	0.47770 (16)	0.10947 (12)	0.5371 (3)	0.0766 (7)
C17	0.59754 (15)	0.09745 (10)	0.5628 (3)	0.0653 (6)
C18	0.89155 (13)	0.14824 (9)	0.7974 (2)	0.0523 (5)
H1	0.86962	0.21742	0.59296	0.0612*
H2	0.73438	0.03977	0.15747	0.0675*
H3	0.69733	−0.06099	−0.05240	0.0857*
H4	0.75608	−0.18873	0.02799	0.0920*
H5	0.85317	−0.21554	0.31735	0.0787*
H7	0.93233	−0.17084	0.63780	0.0627*
H8	0.95707	−0.07359	0.85922	0.0602*
H11	0.82686	0.13419	0.35624	0.0520*
H13	0.65851	0.20496	0.22768	0.0926*
H14	0.45948	0.22429	0.18762	0.1174*
H15	0.34624	0.16371	0.37798	0.0938*
H16	0.43200	0.08537	0.61676	0.0919*
H17	0.63155	0.06536	0.65983	0.0783*

	U11	U22	U33	U12	U13	U23
O1	0.0719 (7)	0.0430 (6)	0.0505 (6)	−0.0007 (5)	0.0006 (5)	−0.0011 (5)
O2	0.0814 (9)	0.0577 (7)	0.0769 (8)	0.0065 (6)	−0.0061 (7)	−0.0244 (6)
N1	0.0508 (7)	0.0327 (6)	0.0675 (9)	−0.0037 (5)	0.0017 (6)	0.0014 (6)
C1	0.0422 (8)	0.0404 (8)	0.0512 (8)	−0.0057 (6)	0.0170 (6)	−0.0019 (6)
C2	0.0645 (10)	0.0564 (9)	0.0502 (9)	−0.0054 (8)	0.0162 (7)	−0.0021 (8)
C3	0.0857 (13)	0.0788 (13)	0.0523 (10)	−0.0123 (10)	0.0180 (9)	−0.0131 (9)
C4	0.0951 (15)	0.0696 (12)	0.0709 (13)	−0.0161 (10)	0.0309 (11)	−0.0278 (10)
C5	0.0740 (12)	0.0438 (9)	0.0859 (13)	−0.0071 (8)	0.0352 (10)	−0.0134 (9)
C6	0.0459 (8)	0.0381 (8)	0.0669 (10)	−0.0049 (6)	0.0236 (7)	−0.0035 (7)
C7	0.0479 (8)	0.0346 (7)	0.0771 (11)	0.0021 (6)	0.0187 (8)	0.0068 (7)
C8	0.0462 (8)	0.0431 (8)	0.0610 (9)	0.0017 (6)	0.0067 (7)	0.0122 (7)
C9	0.0435 (8)	0.0375 (7)	0.0498 (8)	−0.0027 (6)	0.0080 (6)	0.0004 (6)
C10	0.0374 (7)	0.0352 (7)	0.0506 (8)	−0.0022 (5)	0.0113 (6)	0.0032 (6)
C11	0.0459 (8)	0.0354 (7)	0.0491 (8)	−0.0030 (6)	0.0077 (6)	0.0045 (6)
C12	0.0459 (8)	0.0357 (7)	0.0553 (9)	−0.0012 (6)	0.0042 (6)	0.0004 (6)
C13	0.0565 (10)	0.0874 (13)	0.0853 (13)	0.0041 (9)	0.0026 (9)	0.0366 (11)
C14	0.0629 (12)	0.1150 (18)	0.1095 (17)	0.0172 (12)	−0.0088 (12)	0.0423 (14)
C15	0.0478 (10)	0.0796 (13)	0.1042 (15)	0.0064 (9)	0.0009 (10)	−0.0069 (12)
C16	0.0562 (11)	0.0755 (12)	0.1031 (15)	−0.0015 (9)	0.0287 (10)	0.0056 (11)
C17	0.0546 (10)	0.0646 (11)	0.0795 (12)	0.0073 (8)	0.0192 (8)	0.0200 (9)
C18	0.0481 (8)	0.0421 (8)	0.0653 (10)	0.0026 (6)	0.0034 (7)	−0.0061 (8)

O1—C9	1.3958 (17)	C12—C17	1.373 (2)
O1—C18	1.3617 (18)	C12—C13	1.366 (3)
O2—C18	1.2167 (19)	C13—C14	1.384 (3)
N1—C11	1.4622 (19)	C14—C15	1.346 (3)
N1—C18	1.3259 (19)	C15—C16	1.358 (3)
N1—H1	0.8600	C16—C17	1.387 (3)
C1—C2	1.417 (2)	C2—H2	0.9300
C1—C10	1.4280 (19)	C3—H3	0.9300
C1—C6	1.4191 (19)	C4—H4	0.9300
C2—C3	1.365 (3)	C5—H5	0.9300
C3—C4	1.392 (3)	C7—H7	0.9300
C4—C5	1.358 (3)	C8—H8	0.9300
C5—C6	1.418 (2)	C11—H11	0.9800
C6—C7	1.409 (2)	C13—H13	0.9300
C7—C8	1.356 (2)	C14—H14	0.9300
C8—C9	1.4075 (19)	C15—H15	0.9300
C9—C10	1.355 (2)	C16—H16	0.9300
C10—C11	1.5039 (19)	C17—H17	0.9300
C11—C12	1.525 (2)
C9—O1—C18	120.13 (11)	C15—C16—C17	120.35 (19)
C11—N1—C18	126.78 (12)	C12—C17—C16	120.75 (18)
C11—N1—H1	117.00	O2—C18—N1	125.73 (14)
C18—N1—H1	117.00	O1—C18—O2	117.21 (13)
C2—C1—C6	118.33 (13)	O1—C18—N1	117.05 (13)
C6—C1—C10	118.94 (13)	C1—C2—H2	120.00
C2—C1—C10	122.72 (13)	C3—C2—H2	120.00
C1—C2—C3	120.94 (16)	C2—C3—H3	120.00
C2—C3—C4	120.63 (19)	C4—C3—H3	120.00
C3—C4—C5	120.27 (19)	C3—C4—H4	120.00
C4—C5—C6	121.17 (16)	C5—C4—H4	120.00
C5—C6—C7	122.02 (14)	C4—C5—H5	119.00
C1—C6—C5	118.64 (14)	C6—C5—H5	119.00
C1—C6—C7	119.33 (13)	C6—C7—H7	119.00
C6—C7—C8	121.20 (13)	C8—C7—H7	119.00
C7—C8—C9	118.75 (13)	C7—C8—H8	121.00
O1—C9—C10	122.00 (12)	C9—C8—H8	121.00
O1—C9—C8	114.88 (12)	N1—C11—H11	108.00
C8—C9—C10	123.11 (13)	C10—C11—H11	108.00
C1—C10—C11	121.82 (12)	C12—C11—H11	108.00
C1—C10—C9	118.59 (12)	C12—C13—H13	120.00
C9—C10—C11	119.58 (12)	C14—C13—H13	120.00
C10—C11—C12	113.63 (11)	C13—C14—H14	120.00
N1—C11—C12	110.68 (11)	C15—C14—H14	120.00
N1—C11—C10	108.56 (11)	C14—C15—H15	120.00
C11—C12—C13	120.86 (14)	C16—C15—H15	120.00
C11—C12—C17	121.24 (13)	C15—C16—H16	120.00
C13—C12—C17	117.89 (15)	C17—C16—H16	120.00
C12—C13—C14	120.81 (18)	C12—C17—H17	120.00
C13—C14—C15	120.9 (2)	C16—C17—H17	120.00
C14—C15—C16	119.30 (18)
C18—O1—C9—C8	164.13 (13)	C5—C6—C7—C8	−176.94 (15)
C18—O1—C9—C10	−16.9 (2)	C6—C7—C8—C9	−1.2 (2)
C9—O1—C18—O2	−170.95 (14)	C7—C8—C9—O1	177.44 (13)
C9—O1—C18—N1	7.8 (2)	C7—C8—C9—C10	−1.5 (2)
C18—N1—C11—C10	−27.00 (19)	O1—C9—C10—C1	−175.98 (12)
C18—N1—C11—C12	98.36 (16)	O1—C9—C10—C11	3.0 (2)
C11—N1—C18—O1	15.8 (2)	C8—C9—C10—C1	2.9 (2)
C11—N1—C18—O2	−165.56 (15)	C8—C9—C10—C11	−178.08 (13)
C6—C1—C2—C3	1.4 (2)	C1—C10—C11—N1	−164.84 (12)
C10—C1—C2—C3	−177.10 (16)	C1—C10—C11—C12	71.56 (17)
C2—C1—C6—C5	−0.1 (2)	C9—C10—C11—N1	16.17 (17)
C2—C1—C6—C7	−179.36 (14)	C9—C10—C11—C12	−107.43 (15)
C10—C1—C6—C5	178.41 (14)	N1—C11—C12—C13	99.58 (17)
C10—C1—C6—C7	−0.9 (2)	N1—C11—C12—C17	−79.96 (17)
C2—C1—C10—C9	176.78 (14)	C10—C11—C12—C13	−137.98 (16)
C2—C1—C10—C11	−2.2 (2)	C10—C11—C12—C17	42.48 (19)
C6—C1—C10—C9	−1.7 (2)	C11—C12—C13—C14	179.58 (17)
C6—C1—C10—C11	179.35 (13)	C17—C12—C13—C14	−0.9 (3)
C1—C2—C3—C4	−1.2 (3)	C11—C12—C17—C16	−179.52 (16)
C2—C3—C4—C5	−0.2 (3)	C13—C12—C17—C16	0.9 (3)
C3—C4—C5—C6	1.5 (3)	C12—C13—C14—C15	−0.1 (3)
C4—C5—C6—C1	−1.3 (3)	C13—C14—C15—C16	0.9 (3)
C4—C5—C6—C7	177.92 (17)	C14—C15—C16—C17	−0.9 (3)
C1—C6—C7—C8	2.3 (2)	C15—C16—C17—C12	−0.1 (3)

Cg2 is the centroid of the C1–C6 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.07	2.8698 (17)	155
C8—H8···O1ii	0.93	2.58	3.4725 (18)	161
C16—H16···Cg2iii	0.93	2.92	3.722 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.07	2.8698 (17)	155
C8—H8⋯O1ii	0.93	2.58	3.4725 (18)	161
C16—H16⋯Cg2iii	0.93	2.92	3.722 (2)	145

Symmetry codes: (i) ; (ii) ; (iii) .