17-(Pyrimidin-2-yl)-8,16-dioxa-17-aza-tetra-cyclo-[7.7.1.0.0]hepta-deca-2,4,6,10,12,14-hexa-ene.

In the title compound, C(18)H(13)N(3)O(2), the benzene rings form a dihedral angle of 78.49 (9)°. The dihedral angles between the benzene rings and the pyrimidine ring are 76.53 (10) and 27.73 (11)°. The two cis-fused six-membered heterocyclic rings adopt half-chair confirmations. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming chains parallel to the b axis.

Related literature

For the biological activity of Schiff bases, see: Khan et al. (2009 ▶). For the crystal structures of Schiff bases, see: Aslam et al. (2011 ▶); Zeb & Yousuf (2011 ▶). For the importance of carbon–nitro­gen bond-formation reactions for elucidating the mechanism of racemization and transamination reactions in biological systems, see: Lau et al. (1999 ▶).

Experimental

Crystal data

C18H13N3O2

M = 303.31

Monoclinic,

a = 30.004 (4) Å

b = 6.6083 (9) Å

c = 15.123 (2) Å

β = 99.652 (4)°

V = 2956.0 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 273 K

0.54 × 0.09 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.952, T max = 0.993

8329 measured reflections

2739 independent reflections

2026 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.097

S = 1.03

2739 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000931/pv2501sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000931/pv2501Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000931/pv2501Isup3.cml

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

C18H13N3O2	F(000) = 1264
Mr = 303.31	Dx = 1.363 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1521 reflections
a = 30.004 (4) Å	θ = 2.7–21.4°
b = 6.6083 (9) Å	µ = 0.09 mm−1
c = 15.123 (2) Å	T = 273 K
β = 99.652 (4)°	Needle, yellow
V = 2956.0 (7) Å3	0.54 × 0.09 × 0.08 mm
Z = 8

Bruker SMART APEX CCD area-detector diffractometer	2739 independent reflections
Radiation source: fine-focus sealed tube	2026 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scan	θmax = 25.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −36→35
Tmin = 0.952, Tmax = 0.993	k = −8→7
8329 measured reflections	l = −18→18

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0358P)2 + 1.0438P] where P = (Fo2 + 2Fc2)/3
2739 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.12 e Å−3

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	0.14375 (4)	−0.35324 (17)	0.63616 (8)	0.0445 (3)
O2	0.13833 (4)	0.06985 (16)	0.78989 (7)	0.0416 (3)
N1	0.09854 (4)	−0.0699 (2)	0.65391 (9)	0.0406 (4)
N2	0.02176 (5)	−0.1398 (3)	0.63059 (12)	0.0602 (5)
N3	0.04887 (5)	0.2011 (3)	0.64007 (12)	0.0628 (5)
C1	0.13535 (5)	−0.1148 (2)	0.83042 (11)	0.0355 (4)
C2	0.14564 (6)	−0.1211 (3)	0.92321 (11)	0.0437 (4)
H2A	0.1552	−0.0048	0.9555	0.052*
C3	0.14156 (6)	−0.3003 (3)	0.96712 (12)	0.0494 (5)
H3A	0.1485	−0.3050	1.0294	0.059*
C4	0.12721 (6)	−0.4732 (3)	0.91988 (12)	0.0488 (5)
H4A	0.1245	−0.5939	0.9502	0.059*
C5	0.11688 (6)	−0.4670 (3)	0.82775 (12)	0.0414 (4)
H5A	0.1070	−0.5837	0.7961	0.050*
C6	0.12111 (5)	−0.2880 (2)	0.78159 (10)	0.0333 (4)
C7	0.10824 (5)	−0.2779 (3)	0.68069 (11)	0.0380 (4)
H7A	0.0810	−0.3595	0.6622	0.046*
C8	0.18023 (5)	−0.2236 (3)	0.63998 (11)	0.0400 (4)
C9	0.21881 (6)	−0.2982 (3)	0.61168 (12)	0.0504 (5)
H9A	0.2197	−0.4308	0.5914	0.060*
C10	0.25570 (6)	−0.1738 (4)	0.61407 (13)	0.0579 (5)
H10A	0.2816	−0.2231	0.5954	0.070*
C11	0.25481 (6)	0.0230 (4)	0.64381 (13)	0.0571 (5)
H11A	0.2801	0.1056	0.6456	0.069*
C12	0.21623 (6)	0.0969 (3)	0.67091 (12)	0.0483 (5)
H12A	0.2156	0.2298	0.6910	0.058*
C13	0.17824 (5)	−0.0248 (3)	0.66860 (11)	0.0382 (4)
C14	0.13536 (5)	0.0582 (3)	0.69334 (11)	0.0399 (4)
H14A	0.1303	0.1946	0.6682	0.048*
C15	0.05409 (6)	0.0009 (3)	0.64170 (11)	0.0453 (5)
C16	−0.02032 (7)	−0.0673 (4)	0.61509 (18)	0.0796 (7)
H16A	−0.0442	−0.1587	0.6062	0.096*
C17	−0.02996 (8)	0.1338 (5)	0.6117 (2)	0.0925 (9)
H17A	−0.0596	0.1806	0.6009	0.111*
C18	0.00588 (8)	0.2636 (4)	0.62481 (18)	0.0828 (8)
H18A	0.0001	0.4020	0.6231	0.099*

	U11	U22	U33	U12	U13	U23
O1	0.0480 (7)	0.0438 (8)	0.0434 (7)	−0.0028 (6)	0.0124 (5)	−0.0111 (6)
O2	0.0520 (7)	0.0298 (7)	0.0446 (7)	−0.0027 (5)	0.0127 (5)	−0.0019 (5)
N1	0.0359 (8)	0.0398 (9)	0.0447 (8)	0.0015 (6)	0.0026 (6)	0.0035 (7)
N2	0.0370 (9)	0.0657 (12)	0.0771 (12)	−0.0010 (8)	0.0074 (8)	−0.0018 (9)
N3	0.0496 (10)	0.0545 (11)	0.0825 (13)	0.0138 (8)	0.0057 (9)	0.0044 (9)
C1	0.0333 (9)	0.0305 (10)	0.0441 (10)	0.0017 (7)	0.0103 (7)	−0.0010 (8)
C2	0.0492 (10)	0.0399 (11)	0.0425 (10)	−0.0030 (8)	0.0095 (8)	−0.0081 (8)
C3	0.0582 (11)	0.0500 (12)	0.0398 (10)	−0.0014 (9)	0.0075 (9)	0.0010 (9)
C4	0.0578 (12)	0.0384 (11)	0.0510 (12)	−0.0007 (9)	0.0112 (9)	0.0083 (9)
C5	0.0440 (10)	0.0312 (10)	0.0494 (11)	−0.0011 (8)	0.0087 (8)	−0.0027 (8)
C6	0.0299 (8)	0.0303 (9)	0.0405 (9)	0.0016 (7)	0.0082 (7)	−0.0031 (7)
C7	0.0352 (9)	0.0355 (10)	0.0432 (10)	−0.0013 (7)	0.0059 (7)	−0.0047 (8)
C8	0.0408 (9)	0.0479 (11)	0.0311 (9)	−0.0009 (8)	0.0055 (7)	−0.0001 (8)
C9	0.0533 (11)	0.0573 (13)	0.0422 (10)	0.0080 (10)	0.0130 (9)	−0.0030 (9)
C10	0.0432 (11)	0.0820 (17)	0.0509 (12)	0.0062 (11)	0.0145 (9)	0.0035 (11)
C11	0.0421 (11)	0.0755 (16)	0.0543 (12)	−0.0113 (10)	0.0095 (9)	0.0030 (11)
C12	0.0477 (11)	0.0517 (12)	0.0444 (11)	−0.0067 (9)	0.0043 (8)	0.0015 (9)
C13	0.0400 (9)	0.0405 (11)	0.0336 (9)	0.0007 (8)	0.0042 (7)	0.0036 (8)
C14	0.0450 (10)	0.0348 (10)	0.0398 (10)	−0.0011 (8)	0.0068 (8)	0.0050 (8)
C15	0.0422 (10)	0.0535 (13)	0.0405 (10)	0.0071 (9)	0.0081 (8)	0.0030 (9)
C16	0.0400 (12)	0.088 (2)	0.110 (2)	0.0023 (12)	0.0114 (12)	−0.0051 (15)
C17	0.0437 (13)	0.094 (2)	0.137 (2)	0.0221 (14)	0.0056 (14)	−0.0016 (18)
C18	0.0608 (15)	0.0690 (17)	0.116 (2)	0.0225 (13)	0.0080 (14)	0.0020 (14)

O1—C8	1.383 (2)	C5—H5A	0.9300
O1—C7	1.4409 (18)	C6—C7	1.511 (2)
O2—C1	1.3749 (19)	C7—H7A	0.9800
O2—C14	1.4499 (19)	C8—C13	1.387 (2)
N1—C15	1.396 (2)	C8—C9	1.390 (2)
N1—C14	1.440 (2)	C9—C10	1.374 (3)
N1—C7	1.449 (2)	C9—H9A	0.9300
N2—C15	1.334 (2)	C10—C11	1.378 (3)
N2—C16	1.334 (3)	C10—H10A	0.9300
N3—C15	1.333 (2)	C11—C12	1.380 (3)
N3—C18	1.337 (2)	C11—H11A	0.9300
C1—C2	1.386 (2)	C12—C13	1.391 (2)
C1—C6	1.390 (2)	C12—H12A	0.9300
C2—C3	1.373 (2)	C13—C14	1.503 (2)
C2—H2A	0.9300	C14—H14A	0.9800
C3—C4	1.378 (3)	C16—C17	1.359 (3)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.376 (2)	C17—C18	1.364 (3)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.390 (2)	C18—H18A	0.9300
C8—O1—C7	114.10 (13)	C10—C9—C8	119.22 (19)
C1—O2—C14	113.85 (12)	C10—C9—H9A	120.4
C15—N1—C14	120.49 (15)	C8—C9—H9A	120.4
C15—N1—C7	119.85 (14)	C9—C10—C11	120.91 (18)
C14—N1—C7	109.76 (13)	C9—C10—H10A	119.5
C15—N2—C16	114.73 (19)	C11—C10—H10A	119.5
C15—N3—C18	114.63 (19)	C10—C11—C12	119.59 (18)
O2—C1—C2	117.26 (14)	C10—C11—H11A	120.2
O2—C1—C6	122.08 (14)	C12—C11—H11A	120.2
C2—C1—C6	120.62 (15)	C11—C12—C13	120.83 (19)
C3—C2—C1	119.53 (16)	C11—C12—H12A	119.6
C3—C2—H2A	120.2	C13—C12—H12A	119.6
C1—C2—H2A	120.2	C8—C13—C12	118.52 (16)
C2—C3—C4	120.66 (17)	C8—C13—C14	120.47 (15)
C2—C3—H3A	119.7	C12—C13—C14	120.97 (16)
C4—C3—H3A	119.7	N1—C14—O2	111.19 (13)
C5—C4—C3	119.87 (17)	N1—C14—C13	108.15 (14)
C5—C4—H4A	120.1	O2—C14—C13	111.07 (13)
C3—C4—H4A	120.1	N1—C14—H14A	108.8
C4—C5—C6	120.64 (16)	O2—C14—H14A	108.8
C4—C5—H5A	119.7	C13—C14—H14A	108.8
C6—C5—H5A	119.7	N3—C15—N2	127.55 (17)
C5—C6—C1	118.67 (15)	N3—C15—N1	116.23 (16)
C5—C6—C7	121.01 (15)	N2—C15—N1	116.20 (17)
C1—C6—C7	120.25 (14)	N2—C16—C17	123.2 (2)
O1—C7—N1	109.07 (13)	N2—C16—H16A	118.4
O1—C7—C6	111.90 (12)	C17—C16—H16A	118.4
N1—C7—C6	109.23 (13)	C16—C17—C18	116.9 (2)
O1—C7—H7A	108.9	C16—C17—H17A	121.6
N1—C7—H7A	108.9	C18—C17—H17A	121.6
C6—C7—H7A	108.9	N3—C18—C17	123.0 (2)
O1—C8—C13	121.61 (15)	N3—C18—H18A	118.5
O1—C8—C9	117.48 (16)	C17—C18—H18A	118.5
C13—C8—C9	120.89 (17)
C14—O2—C1—C2	169.13 (14)	C10—C11—C12—C13	0.0 (3)
C14—O2—C1—C6	−13.1 (2)	O1—C8—C13—C12	179.89 (14)
O2—C1—C2—C3	177.58 (15)	C9—C8—C13—C12	−1.9 (2)
C6—C1—C2—C3	−0.2 (2)	O1—C8—C13—C14	−2.2 (2)
C1—C2—C3—C4	−0.2 (3)	C9—C8—C13—C14	175.99 (15)
C2—C3—C4—C5	0.1 (3)	C11—C12—C13—C8	1.2 (2)
C3—C4—C5—C6	0.5 (3)	C11—C12—C13—C14	−176.69 (16)
C4—C5—C6—C1	−0.9 (2)	C15—N1—C14—O2	77.64 (18)
C4—C5—C6—C7	−177.79 (15)	C7—N1—C14—O2	−67.97 (16)
O2—C1—C6—C5	−176.91 (14)	C15—N1—C14—C13	−160.16 (14)
C2—C1—C6—C5	0.8 (2)	C7—N1—C14—C13	54.23 (17)
O2—C1—C6—C7	0.0 (2)	C1—O2—C14—N1	46.56 (17)
C2—C1—C6—C7	177.66 (14)	C1—O2—C14—C13	−73.93 (16)
C8—O1—C7—N1	46.98 (17)	C8—C13—C14—N1	−19.1 (2)
C8—O1—C7—C6	−73.99 (17)	C12—C13—C14—N1	158.72 (15)
C15—N1—C7—O1	143.14 (14)	C8—C13—C14—O2	103.18 (17)
C14—N1—C7—O1	−70.99 (16)	C12—C13—C14—O2	−79.01 (19)
C15—N1—C7—C6	−94.27 (17)	C18—N3—C15—N2	−0.5 (3)
C14—N1—C7—C6	51.60 (17)	C18—N3—C15—N1	177.54 (18)
C5—C6—C7—O1	−81.72 (18)	C16—N2—C15—N3	0.9 (3)
C1—C6—C7—O1	101.46 (17)	C16—N2—C15—N1	−177.13 (18)
C5—C6—C7—N1	157.40 (14)	C14—N1—C15—N3	21.1 (2)
C1—C6—C7—N1	−19.42 (19)	C7—N1—C15—N3	163.28 (15)
C7—O1—C8—C13	−11.9 (2)	C14—N1—C15—N2	−160.68 (15)
C7—O1—C8—C9	169.77 (14)	C7—N1—C15—N2	−18.5 (2)
O1—C8—C9—C10	179.70 (15)	C15—N2—C16—C17	−0.7 (4)
C13—C8—C9—C10	1.4 (3)	N2—C16—C17—C18	0.2 (4)
C8—C9—C10—C11	−0.2 (3)	C15—N3—C18—C17	−0.1 (4)
C9—C10—C11—C12	−0.5 (3)	C16—C17—C18—N3	0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O2i	0.93	2.48	3.199 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O2i	0.93	2.48	3.199 (2)	134

Symmetry code: (i) .