N-(1-Naphth-yl)-10H-9-oxa-1,3-diaza-anthracen-4-amine.

In the mol-ecule of the title compound, C(21)H(15)N(3)O, the 10H-9-oxa-1,3-diaza-anthracene ring system is slightly bent, with dihedral angles of 3.99 (6) and 4.80 (6)° between the pyran ring and the pyrimidine and benzene rings, respectively. This ring system makes a dihedral angle of 85.23 (3)° with the naphthalene plane. In the crystal packing, mol-ecules are linked by N-H⋯N hydrogen bonds into chains along the a axis and these chains are stacked along the b axis. The crystal is further stabilized by weak C-H⋯N and C-H⋯π inter-actions.

Related literature

For values of bond lengths, see Allen et al. (1987 ▶). For background to the bioactivity and applications of naphthyrimidines, see, for example: Bedard et al. (2000 ▶); Bohme & Haake (1976 ▶); Erian (1993 ▶); Falardeau et al. (2000 ▶); Martinez & Marco (1997 ▶); Tandon et al. (1991 ▶); Taylor & McKillop (1970 ▶). For the stability of the temperature controller, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H15N3O

M = 325.36

Orthorhombic,

a = 13.2762 (3) Å

b = 8.8700 (2) Å

c = 27.1997 (5) Å

V = 3203.03 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.57 × 0.38 × 0.03 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.901, T max = 0.997

27104 measured reflections

4673 independent reflections

3649 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.142

S = 1.08

4673 reflections

230 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004693/sj2571sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004693/sj2571Isup2.hkl

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

C21H15N3O	Dx = 1.349 Mg m−3
Mr = 325.36	Melting point = 513–515 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4673 reflections
a = 13.2762 (3) Å	θ = 1.5–30.0°
b = 8.8700 (2) Å	µ = 0.09 mm−1
c = 27.1997 (5) Å	T = 100 K
V = 3203.03 (12) Å3	Plate, colourless
Z = 8	0.57 × 0.38 × 0.03 mm
F(000) = 1360

Bruker SMART APEXII CCD area-detector diffractometer	4673 independent reflections
Radiation source: fine-focus sealed tube	3649 reflections with I > 2σ(I)
graphite	Rint = 0.042
Detector resolution: 8.33 pixels mm-1	θmax = 30.0°, θmin = 1.5°
ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
Tmin = 0.901, Tmax = 0.997	l = −37→38
27104 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0844P)2 + 0.3525P] where P = (Fo2 + 2Fc2)/3
4673 reflections	(Δ/σ)max = 0.001
230 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
O1	0.08414 (6)	0.31457 (10)	0.18202 (3)	0.0193 (2)
N1	0.18466 (7)	0.51429 (12)	0.30718 (4)	0.0183 (2)
N2	0.05453 (7)	0.44680 (12)	0.25056 (3)	0.0180 (2)
N3	0.35056 (7)	0.44664 (13)	0.29448 (3)	0.0182 (2)
H1N3	0.4016 (12)	0.4226 (19)	0.2734 (6)	0.034 (4)*
C1	0.25345 (8)	0.44337 (14)	0.27880 (4)	0.0156 (2)
C2	0.09044 (9)	0.51210 (15)	0.29118 (4)	0.0184 (2)
H2A	0.0435	0.5622	0.3106	0.022*
C3	0.12498 (8)	0.37767 (14)	0.22322 (4)	0.0163 (2)
C4	0.14513 (9)	0.22381 (14)	0.15270 (4)	0.0174 (2)
C5	0.09574 (9)	0.15384 (16)	0.11364 (4)	0.0220 (3)
H5A	0.0277	0.1716	0.1081	0.026*
C6	0.14946 (10)	0.05735 (16)	0.08316 (4)	0.0245 (3)
H6A	0.1175	0.0100	0.0569	0.029*
C7	0.25153 (10)	0.03159 (16)	0.09199 (4)	0.0234 (3)
H7A	0.2873	−0.0352	0.0723	0.028*
C8	0.29956 (9)	0.10591 (15)	0.13028 (4)	0.0202 (3)
H8A	0.3679	0.0893	0.1355	0.024*
C9	0.24765 (8)	0.20522 (14)	0.16123 (4)	0.0169 (2)
C10	0.30044 (8)	0.29292 (15)	0.20116 (4)	0.0178 (2)
H10A	0.3420	0.2249	0.2204	0.021*
H10B	0.3442	0.3677	0.1863	0.021*
C11	0.22622 (8)	0.37036 (14)	0.23449 (4)	0.0156 (2)
C12	0.37886 (8)	0.52034 (15)	0.33935 (4)	0.0175 (2)
C13	0.41910 (9)	0.66208 (16)	0.33759 (4)	0.0218 (3)
H13A	0.4274	0.7097	0.3074	0.026*
C14	0.44831 (10)	0.73748 (16)	0.38139 (5)	0.0247 (3)
H14A	0.4748	0.8344	0.3798	0.030*
C15	0.43757 (9)	0.66800 (16)	0.42576 (5)	0.0240 (3)
H15A	0.4560	0.7185	0.4543	0.029*
C16	0.39841 (9)	0.51891 (16)	0.42882 (4)	0.0210 (3)
C17	0.38629 (10)	0.44401 (18)	0.47457 (4)	0.0273 (3)
H17A	0.4035	0.4937	0.5035	0.033*
C18	0.34979 (10)	0.30001 (19)	0.47687 (5)	0.0310 (3)
H18A	0.3425	0.2527	0.5072	0.037*
C19	0.32313 (10)	0.22321 (18)	0.43346 (5)	0.0272 (3)
H19A	0.3001	0.1243	0.4352	0.033*
C20	0.33080 (9)	0.29311 (16)	0.38844 (4)	0.0215 (3)
H20A	0.3113	0.2422	0.3601	0.026*
C21	0.36831 (8)	0.44257 (15)	0.38505 (4)	0.0179 (2)

	U11	U22	U33	U12	U13	U23
O1	0.0145 (4)	0.0257 (5)	0.0178 (4)	0.0017 (3)	−0.0020 (3)	−0.0046 (3)
N1	0.0160 (5)	0.0215 (5)	0.0175 (4)	0.0021 (4)	0.0008 (3)	−0.0018 (4)
N2	0.0145 (4)	0.0211 (5)	0.0183 (4)	0.0019 (4)	−0.0010 (3)	0.0001 (4)
N3	0.0128 (4)	0.0267 (6)	0.0152 (4)	0.0008 (4)	−0.0012 (3)	−0.0035 (4)
C1	0.0141 (5)	0.0170 (6)	0.0156 (4)	0.0002 (4)	−0.0003 (4)	0.0016 (4)
C2	0.0163 (5)	0.0212 (6)	0.0178 (5)	0.0019 (5)	0.0020 (4)	−0.0005 (4)
C3	0.0167 (5)	0.0181 (6)	0.0141 (4)	0.0002 (5)	−0.0002 (4)	0.0009 (4)
C4	0.0174 (5)	0.0189 (6)	0.0158 (5)	−0.0008 (5)	0.0009 (4)	0.0005 (4)
C5	0.0202 (6)	0.0272 (7)	0.0186 (5)	−0.0035 (5)	−0.0012 (4)	0.0005 (5)
C6	0.0279 (6)	0.0277 (7)	0.0178 (5)	−0.0051 (5)	−0.0005 (4)	−0.0030 (5)
C7	0.0279 (6)	0.0238 (7)	0.0185 (5)	−0.0003 (5)	0.0052 (5)	−0.0019 (5)
C8	0.0205 (5)	0.0217 (6)	0.0182 (5)	0.0016 (5)	0.0033 (4)	0.0015 (5)
C9	0.0183 (5)	0.0177 (6)	0.0148 (4)	−0.0004 (4)	0.0011 (4)	0.0009 (4)
C10	0.0138 (5)	0.0225 (6)	0.0171 (5)	0.0012 (4)	0.0001 (4)	−0.0019 (4)
C11	0.0152 (5)	0.0173 (6)	0.0144 (4)	0.0008 (4)	−0.0001 (4)	0.0006 (4)
C12	0.0131 (5)	0.0227 (6)	0.0167 (5)	0.0023 (4)	−0.0006 (4)	−0.0028 (4)
C13	0.0198 (6)	0.0243 (7)	0.0213 (5)	0.0001 (5)	−0.0028 (4)	0.0021 (5)
C14	0.0228 (6)	0.0215 (6)	0.0297 (6)	−0.0039 (5)	−0.0053 (5)	−0.0025 (5)
C15	0.0211 (6)	0.0282 (7)	0.0227 (5)	−0.0001 (5)	−0.0047 (4)	−0.0069 (5)
C16	0.0160 (5)	0.0288 (7)	0.0183 (5)	0.0003 (5)	−0.0015 (4)	−0.0033 (5)
C17	0.0223 (6)	0.0427 (9)	0.0169 (5)	−0.0020 (6)	−0.0022 (4)	−0.0014 (5)
C18	0.0262 (6)	0.0453 (9)	0.0214 (6)	−0.0048 (6)	−0.0008 (5)	0.0080 (6)
C19	0.0220 (6)	0.0311 (8)	0.0285 (6)	−0.0060 (6)	−0.0003 (5)	0.0049 (6)
C20	0.0173 (5)	0.0252 (7)	0.0218 (5)	−0.0017 (5)	−0.0003 (4)	−0.0016 (5)
C21	0.0128 (5)	0.0233 (6)	0.0176 (5)	0.0019 (5)	−0.0007 (4)	−0.0026 (5)

O1—C3	1.3649 (13)	C9—C10	1.5085 (16)
O1—C4	1.3927 (14)	C10—C11	1.5050 (15)
N1—C2	1.3245 (15)	C10—H10A	0.9700
N1—C1	1.3511 (14)	C10—H10B	0.9700
N2—C2	1.3355 (15)	C12—C13	1.3669 (19)
N2—C3	1.3432 (15)	C12—C21	1.4287 (16)
N3—C1	1.3582 (14)	C13—C14	1.4202 (17)
N3—C12	1.4345 (14)	C13—H13A	0.9300
N3—H1N3	0.913 (17)	C14—C15	1.3626 (18)
C1—C11	1.4151 (15)	C14—H14A	0.9300
C2—H2A	0.9300	C15—C16	1.4234 (19)
C3—C11	1.3800 (15)	C15—H15A	0.9300
C4—C9	1.3905 (16)	C16—C17	1.4198 (17)
C4—C5	1.3943 (16)	C16—C21	1.4266 (16)
C5—C6	1.3886 (18)	C17—C18	1.368 (2)
C5—H5A	0.9300	C17—H17A	0.9300
C6—C7	1.3951 (19)	C18—C19	1.4082 (19)
C6—H6A	0.9300	C18—H18A	0.9300
C7—C8	1.3878 (17)	C19—C20	1.3764 (17)
C7—H7A	0.9300	C19—H19A	0.9300
C8—C9	1.3999 (16)	C20—C21	1.4191 (19)
C8—H8A	0.9300	C20—H20A	0.9300
C3—O1—C4	118.43 (9)	C11—C10—H10B	109.3
C2—N1—C1	116.35 (10)	C9—C10—H10B	109.3
C2—N2—C3	114.05 (10)	H10A—C10—H10B	108.0
C1—N3—C12	121.70 (10)	C3—C11—C1	114.62 (10)
C1—N3—H1N3	120.1 (10)	C3—C11—C10	121.68 (10)
C12—N3—H1N3	116.5 (10)	C1—C11—C10	123.68 (10)
N1—C1—N3	116.89 (10)	C13—C12—C21	120.85 (11)
N1—C1—C11	121.79 (10)	C13—C12—N3	119.46 (11)
N3—C1—C11	121.31 (10)	C21—C12—N3	119.64 (11)
N1—C2—N2	127.97 (11)	C12—C13—C14	120.70 (11)
N1—C2—H2A	116.0	C12—C13—H13A	119.6
N2—C2—H2A	116.0	C14—C13—H13A	119.6
N2—C3—O1	111.42 (9)	C15—C14—C13	120.09 (12)
N2—C3—C11	125.21 (10)	C15—C14—H14A	120.0
O1—C3—C11	123.37 (10)	C13—C14—H14A	120.0
C9—C4—O1	122.82 (10)	C14—C15—C16	120.68 (11)
C9—C4—C5	122.33 (11)	C14—C15—H15A	119.7
O1—C4—C5	114.85 (10)	C16—C15—H15A	119.7
C6—C5—C4	119.18 (11)	C17—C16—C15	121.83 (11)
C6—C5—H5A	120.4	C17—C16—C21	118.52 (12)
C4—C5—H5A	120.4	C15—C16—C21	119.64 (11)
C5—C6—C7	119.81 (11)	C18—C17—C16	121.15 (12)
C5—C6—H6A	120.1	C18—C17—H17A	119.4
C7—C6—H6A	120.1	C16—C17—H17A	119.4
C8—C7—C6	119.84 (12)	C17—C18—C19	120.17 (12)
C8—C7—H7A	120.1	C17—C18—H18A	119.9
C6—C7—H7A	120.1	C19—C18—H18A	119.9
C7—C8—C9	121.60 (11)	C20—C19—C18	120.62 (14)
C7—C8—H8A	119.2	C20—C19—H19A	119.7
C9—C8—H8A	119.2	C18—C19—H19A	119.7
C4—C9—C8	117.14 (10)	C19—C20—C21	120.30 (12)
C4—C9—C10	120.92 (10)	C19—C20—H20A	119.8
C8—C9—C10	121.91 (10)	C21—C20—H20A	119.8
C11—C10—C9	111.40 (9)	C20—C21—C16	119.18 (11)
C11—C10—H10A	109.3	C20—C21—C12	122.82 (11)
C9—C10—H10A	109.3	C16—C21—C12	118.00 (11)
C2—N1—C1—N3	179.12 (11)	N1—C1—C11—C3	−0.19 (17)
C2—N1—C1—C11	−0.19 (17)	N3—C1—C11—C3	−179.46 (11)
C12—N3—C1—N1	0.71 (17)	N1—C1—C11—C10	178.62 (11)
C12—N3—C1—C11	−179.98 (11)	N3—C1—C11—C10	−0.66 (18)
C1—N1—C2—N2	0.81 (19)	C9—C10—C11—C3	−10.17 (16)
C3—N2—C2—N1	−0.92 (19)	C9—C10—C11—C1	171.11 (11)
C2—N2—C3—O1	−179.33 (10)	C1—N3—C12—C13	−99.41 (14)
C2—N2—C3—C11	0.44 (18)	C1—N3—C12—C21	83.00 (15)
C4—O1—C3—N2	−172.67 (10)	C21—C12—C13—C14	−2.11 (18)
C4—O1—C3—C11	7.55 (17)	N3—C12—C13—C14	−179.66 (11)
C3—O1—C4—C9	−5.68 (16)	C12—C13—C14—C15	0.8 (2)
C3—O1—C4—C5	174.98 (11)	C13—C14—C15—C16	0.9 (2)
C9—C4—C5—C6	2.60 (19)	C14—C15—C16—C17	−179.90 (12)
O1—C4—C5—C6	−178.05 (11)	C14—C15—C16—C21	−1.21 (18)
C4—C5—C6—C7	0.09 (19)	C15—C16—C17—C18	−179.14 (12)
C5—C6—C7—C8	−1.9 (2)	C21—C16—C17—C18	2.15 (19)
C6—C7—C8—C9	1.13 (19)	C16—C17—C18—C19	−0.2 (2)
O1—C4—C9—C8	177.40 (11)	C17—C18—C19—C20	−1.8 (2)
C5—C4—C9—C8	−3.31 (18)	C18—C19—C20—C21	1.7 (2)
O1—C4—C9—C10	−4.59 (17)	C19—C20—C21—C16	0.33 (18)
C5—C4—C9—C10	174.71 (11)	C19—C20—C21—C12	179.40 (12)
C7—C8—C9—C4	1.42 (18)	C17—C16—C21—C20	−2.21 (17)
C7—C8—C9—C10	−176.57 (12)	C15—C16—C21—C20	179.06 (11)
C4—C9—C10—C11	11.79 (16)	C17—C16—C21—C12	178.68 (11)
C8—C9—C10—C11	−170.29 (11)	C15—C16—C21—C12	−0.06 (17)
N2—C3—C11—C1	0.05 (18)	C13—C12—C21—C20	−177.38 (11)
O1—C3—C11—C1	179.80 (10)	N3—C12—C21—C20	0.17 (17)
N2—C3—C11—C10	−178.78 (11)	C13—C12—C21—C16	1.70 (17)
O1—C3—C11—C10	0.97 (18)	N3—C12—C21—C16	179.25 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···N2i	0.913 (16)	2.143 (16)	2.9722 (13)	150.6 (14)
C13—H13A···N2ii	0.93	2.62	3.4791 (16)	154
C20—H20A···N3	0.93	2.60	2.9077 (15)	100
C20—H20A···N1iii	0.93	2.48	3.3232 (17)	150
C10—H10A···Cg1iii	0.97	2.76	3.5855 (14)	143
C10—H10B···Cg2ii	0.97	2.96	3.6792 (14)	132
C13—H13A···Cg1ii	0.93	2.63	3.3503 (14)	135

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C3/C11/N1/N2 and C4–C9 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯N2i	0.913 (16)	2.143 (16)	2.9722 (13)	150.6 (14)
C13—H13A⋯N2ii	0.93	2.62	3.4791 (16)	154
C20—H20A⋯N3	0.93	2.60	2.9077 (15)	100
C20—H20A⋯N1iii	0.93	2.48	3.3232 (17)	150
C10—H10A⋯Cg1iii	0.97	2.76	3.5855 (14)	143
C10—H10B⋯Cg2ii	0.97	2.96	3.6792 (14)	132
C13—H13A⋯Cg1ii	0.93	2.63	3.3503 (14)	135

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