Methyl 6-(4-chloro-phen-yl)-2,4-dimethyl-1,3-dioxo-1,2,3,4,6,6a,7,12b-octa-hydro-chromeno[4',3':4,5]pyrano[2,3-d]pyrimidine-6a-carboxyl-ate.

In the title compound, C(24)H(21)ClN(2)O(6), the two fused six-membered pyran rings adopt half-chair conformations. The dihedral angle between the pyrimidine ring and the chloro-phenyl ring is 51.55 (3)°. In the crystal, mol-ecules are linked by pairs of weak inter-molecular C-H⋯O hydrogen bonds, forming inversion dimers. A C-H⋯π inter-action is also observed.

Related literature

For biological activity of pyrimidine derivatives, see: Alam et al. (2005 ▶); Kappe (2000 ▶); Condon et al. (1993 ▶); Rovnyak et al. (1995 ▶); Leite et al. (2006 ▶); Sriram et al. (2006 ▶). For related structures, see: Booysen et al. (2011 ▶); Noroozi Pesyan et al. (2009 ▶).

Experimental

Crystal data

C24H21ClN2O6

M = 468.88

Monoclinic,

a = 10.6177 (5) Å

b = 11.9973 (5) Å

c = 17.5532 (8) Å

β = 99.751 (2)°

V = 2203.69 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 295 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.924, T max = 0.951

29343 measured reflections

7232 independent reflections

4518 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.158

S = 1.03

7232 reflections

301 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.60 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681102678X/is2742sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102678X/is2742Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681102678X/is2742Isup3.cml

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

C24H21ClN2O6	F(000) = 976
Mr = 468.88	Dx = 1.413 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7610 reflections
a = 10.6177 (5) Å	θ = 2.2–30.2°
b = 11.9973 (5) Å	µ = 0.22 mm−1
c = 17.5532 (8) Å	T = 295 K
β = 99.751 (2)°	Block, colourless
V = 2203.69 (17) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	7232 independent reflections
Radiation source: fine-focus sealed tube	4518 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 0 pixels mm-1	θmax = 31.7°, θmin = 2.1°
ω and φ scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −15→17
Tmin = 0.924, Tmax = 0.951	l = −25→25
29343 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0706P)2 + 0.6194P] where P = (Fo2 + 2Fc2)/3
7232 reflections	(Δ/σ)max = 0.005
301 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.60 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.76555 (18)	0.06202 (16)	0.37637 (10)	0.0480 (4)
H1	0.7599	0.1389	0.3819	0.058*
C2	0.8645 (2)	0.00508 (18)	0.42011 (11)	0.0568 (5)
H2	0.9268	0.0436	0.4536	0.068*
C3	0.87131 (19)	−0.10942 (17)	0.41423 (11)	0.0541 (5)
H3	0.9383	−0.1480	0.4438	0.065*
C4	0.77967 (17)	−0.16628 (15)	0.36499 (10)	0.0459 (4)
H4	0.7837	−0.2435	0.3616	0.055*
C5	0.68080 (14)	−0.10821 (13)	0.32016 (9)	0.0361 (3)
C6	0.47962 (14)	−0.12010 (12)	0.23307 (8)	0.0338 (3)
H6A	0.4081	−0.1706	0.2327	0.041*
H6B	0.4906	−0.1088	0.1799	0.041*
C7	0.44663 (14)	−0.00850 (12)	0.26651 (8)	0.0310 (3)
C8	0.56484 (14)	0.06889 (12)	0.27607 (8)	0.0328 (3)
H8	0.5464	0.1355	0.3046	0.039*
C9	0.67411 (15)	0.00706 (13)	0.32418 (9)	0.0351 (3)
C10	0.33697 (14)	0.05058 (13)	0.21285 (8)	0.0338 (3)
H10	0.3240	0.1238	0.2350	0.041*
C11	0.49137 (15)	0.10189 (13)	0.13570 (9)	0.0362 (3)
C12	0.58675 (15)	0.10449 (13)	0.19648 (9)	0.0356 (3)
C13	0.70722 (17)	0.15057 (14)	0.18445 (11)	0.0438 (4)
C14	0.6217 (2)	0.16628 (16)	0.04577 (11)	0.0510 (4)
C15	0.21085 (14)	−0.00924 (13)	0.19859 (9)	0.0356 (3)
C16	0.18358 (16)	−0.09052 (16)	0.14232 (10)	0.0464 (4)
H16	0.2442	−0.1090	0.1119	0.056*
C17	0.06716 (18)	−0.14441 (18)	0.13101 (11)	0.0529 (5)
H17	0.0493	−0.1992	0.0932	0.063*
C18	−0.02226 (16)	−0.11680 (17)	0.17584 (11)	0.0482 (4)
C19	0.00161 (17)	−0.03659 (19)	0.23166 (12)	0.0550 (5)
H19	−0.0595	−0.0188	0.2619	0.066*
C20	0.11761 (17)	0.01751 (16)	0.24245 (11)	0.0483 (4)
H20	0.1339	0.0730	0.2798	0.058*
C21	0.3952 (2)	0.13297 (19)	−0.00072 (10)	0.0597 (5)
H21A	0.3603	0.0592	−0.0081	0.090*
H21B	0.4218	0.1577	−0.0475	0.090*
H21C	0.3312	0.1828	0.0123	0.090*
C22	0.8425 (2)	0.2140 (3)	0.09356 (16)	0.0834 (8)
H22A	0.8659	0.1797	0.0486	0.125*
H22B	0.9071	0.1990	0.1376	0.125*
H22C	0.8348	0.2931	0.0857	0.125*
C23	0.40621 (15)	−0.02757 (14)	0.34447 (9)	0.0364 (3)
C24	0.3303 (3)	0.0581 (2)	0.44840 (13)	0.0941 (10)
H24A	0.3101	−0.0184	0.4569	0.141*
H24B	0.2547	0.1028	0.4461	0.141*
H24C	0.3943	0.0835	0.4901	0.141*
N1	0.50522 (15)	0.13185 (13)	0.06206 (8)	0.0447 (3)
N2	0.71979 (16)	0.16862 (13)	0.10700 (10)	0.0523 (4)
O1	0.59218 (11)	−0.17168 (9)	0.27413 (7)	0.0444 (3)
O2	0.37171 (11)	0.06736 (10)	0.13744 (6)	0.0408 (3)
O3	0.63502 (17)	0.19131 (14)	−0.01960 (8)	0.0738 (5)
O4	0.79552 (13)	0.17313 (13)	0.23567 (9)	0.0621 (4)
O5	0.39933 (16)	−0.11577 (11)	0.37358 (8)	0.0623 (4)
O6	0.37805 (15)	0.06763 (11)	0.37639 (7)	0.0581 (4)
Cl1	−0.16887 (5)	−0.18537 (6)	0.16129 (4)	0.0765 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0536 (10)	0.0389 (9)	0.0480 (9)	−0.0044 (8)	−0.0018 (8)	−0.0048 (7)
C2	0.0545 (11)	0.0559 (12)	0.0523 (10)	−0.0036 (9)	−0.0128 (8)	−0.0078 (9)
C3	0.0480 (10)	0.0566 (12)	0.0523 (10)	0.0083 (9)	−0.0069 (8)	−0.0013 (9)
C4	0.0447 (9)	0.0387 (9)	0.0527 (10)	0.0080 (7)	0.0033 (7)	−0.0013 (7)
C5	0.0350 (7)	0.0340 (8)	0.0392 (7)	0.0002 (6)	0.0056 (6)	−0.0032 (6)
C6	0.0363 (7)	0.0289 (7)	0.0357 (7)	0.0003 (6)	0.0046 (6)	−0.0008 (6)
C7	0.0342 (7)	0.0277 (7)	0.0316 (6)	0.0001 (5)	0.0076 (5)	0.0014 (5)
C8	0.0373 (7)	0.0258 (7)	0.0356 (7)	−0.0010 (6)	0.0074 (6)	−0.0005 (5)
C9	0.0371 (8)	0.0309 (8)	0.0369 (7)	−0.0015 (6)	0.0050 (6)	−0.0003 (6)
C10	0.0382 (7)	0.0314 (8)	0.0327 (7)	0.0036 (6)	0.0089 (6)	0.0025 (6)
C11	0.0462 (8)	0.0288 (8)	0.0361 (7)	0.0018 (6)	0.0142 (6)	0.0033 (6)
C12	0.0397 (8)	0.0287 (7)	0.0407 (8)	0.0012 (6)	0.0135 (6)	0.0025 (6)
C13	0.0435 (9)	0.0366 (9)	0.0549 (10)	0.0011 (7)	0.0191 (8)	0.0027 (7)
C14	0.0686 (12)	0.0424 (10)	0.0490 (10)	0.0040 (8)	0.0307 (9)	0.0009 (8)
C15	0.0343 (7)	0.0363 (8)	0.0360 (7)	0.0054 (6)	0.0057 (6)	0.0018 (6)
C16	0.0396 (8)	0.0580 (11)	0.0432 (9)	−0.0004 (8)	0.0113 (7)	−0.0102 (8)
C17	0.0461 (10)	0.0610 (12)	0.0499 (10)	−0.0055 (8)	0.0037 (8)	−0.0112 (9)
C18	0.0334 (8)	0.0594 (12)	0.0504 (9)	−0.0006 (7)	0.0030 (7)	0.0066 (8)
C19	0.0386 (9)	0.0707 (13)	0.0592 (11)	0.0044 (9)	0.0179 (8)	−0.0048 (10)
C20	0.0430 (9)	0.0516 (11)	0.0526 (10)	0.0039 (8)	0.0149 (8)	−0.0100 (8)
C21	0.0799 (14)	0.0630 (13)	0.0364 (9)	0.0073 (11)	0.0098 (9)	0.0083 (8)
C22	0.0676 (15)	0.099 (2)	0.0960 (18)	−0.0118 (13)	0.0491 (14)	0.0139 (15)
C23	0.0387 (8)	0.0362 (8)	0.0351 (7)	0.0014 (6)	0.0086 (6)	0.0029 (6)
C24	0.159 (3)	0.0829 (18)	0.0556 (13)	0.0290 (18)	0.0609 (16)	0.0027 (12)
N1	0.0588 (9)	0.0422 (8)	0.0361 (7)	0.0027 (7)	0.0168 (6)	0.0048 (6)
N2	0.0549 (9)	0.0483 (9)	0.0621 (10)	−0.0012 (7)	0.0342 (8)	0.0029 (7)
O1	0.0370 (6)	0.0292 (6)	0.0629 (7)	0.0029 (4)	−0.0030 (5)	−0.0083 (5)
O2	0.0430 (6)	0.0459 (7)	0.0333 (5)	−0.0026 (5)	0.0057 (4)	0.0076 (5)
O3	0.1000 (12)	0.0798 (11)	0.0528 (8)	0.0023 (9)	0.0455 (8)	0.0096 (7)
O4	0.0462 (7)	0.0716 (10)	0.0697 (9)	−0.0159 (7)	0.0130 (7)	0.0056 (7)
O5	0.0981 (11)	0.0404 (8)	0.0562 (8)	0.0018 (7)	0.0359 (8)	0.0126 (6)
O6	0.0926 (11)	0.0442 (7)	0.0451 (7)	0.0092 (7)	0.0330 (7)	−0.0009 (5)
Cl1	0.0427 (3)	0.1053 (5)	0.0794 (4)	−0.0208 (3)	0.0046 (2)	0.0005 (3)

C1—C2	1.374 (3)	C13—N2	1.405 (2)
C1—C9	1.384 (2)	C14—O3	1.217 (2)
C1—H1	0.9300	C14—N2	1.364 (3)
C2—C3	1.380 (3)	C14—N1	1.379 (2)
C2—H2	0.9300	C15—C16	1.383 (2)
C3—C4	1.369 (3)	C15—C20	1.391 (2)
C3—H3	0.9300	C16—C17	1.379 (3)
C4—C5	1.388 (2)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.372 (3)
C5—O1	1.3639 (18)	C17—H17	0.9300
C5—C9	1.387 (2)	C18—C19	1.366 (3)
C6—O1	1.4280 (18)	C18—Cl1	1.7408 (18)
C6—C7	1.526 (2)	C19—C20	1.377 (3)
C6—H6A	0.9700	C19—H19	0.9300
C6—H6B	0.9700	C20—H20	0.9300
C7—C23	1.519 (2)	C21—N1	1.464 (2)
C7—C10	1.541 (2)	C21—H21A	0.9600
C7—C8	1.547 (2)	C21—H21B	0.9600
C8—C9	1.509 (2)	C21—H21C	0.9600
C8—C12	1.516 (2)	C22—N2	1.468 (2)
C8—H8	0.9800	C22—H22A	0.9600
C10—O2	1.4471 (17)	C22—H22B	0.9600
C10—C15	1.502 (2)	C22—H22C	0.9600
C10—H10	0.9800	C23—O5	1.183 (2)
C11—C12	1.341 (2)	C23—O6	1.328 (2)
C11—O2	1.3416 (19)	C24—O6	1.444 (2)
C11—N1	1.3734 (19)	C24—H24A	0.9600
C12—C13	1.442 (2)	C24—H24B	0.9600
C13—O4	1.214 (2)	C24—H24C	0.9600
C2—C1—C9	121.17 (17)	O3—C14—N2	122.88 (19)
C2—C1—H1	119.4	O3—C14—N1	121.4 (2)
C9—C1—H1	119.4	N2—C14—N1	115.75 (15)
C1—C2—C3	119.86 (17)	C16—C15—C20	118.39 (16)
C1—C2—H2	120.1	C16—C15—C10	121.91 (14)
C3—C2—H2	120.1	C20—C15—C10	119.70 (15)
C4—C3—C2	120.16 (17)	C17—C16—C15	120.49 (16)
C4—C3—H3	119.9	C17—C16—H16	119.8
C2—C3—H3	119.9	C15—C16—H16	119.8
C3—C4—C5	119.75 (17)	C18—C17—C16	119.64 (18)
C3—C4—H4	120.1	C18—C17—H17	120.2
C5—C4—H4	120.1	C16—C17—H17	120.2
O1—C5—C9	123.41 (14)	C19—C18—C17	121.26 (17)
O1—C5—C4	115.80 (15)	C19—C18—Cl1	119.39 (14)
C9—C5—C4	120.79 (15)	C17—C18—Cl1	119.35 (15)
O1—C6—C7	114.40 (12)	C18—C19—C20	118.93 (17)
O1—C6—H6A	108.7	C18—C19—H19	120.5
C7—C6—H6A	108.7	C20—C19—H19	120.5
O1—C6—H6B	108.7	C19—C20—C15	121.28 (17)
C7—C6—H6B	108.7	C19—C20—H20	119.4
H6A—C6—H6B	107.6	C15—C20—H20	119.4
C23—C7—C6	109.42 (12)	N1—C21—H21A	109.5
C23—C7—C10	108.69 (12)	N1—C21—H21B	109.5
C6—C7—C10	111.56 (12)	H21A—C21—H21B	109.5
C23—C7—C8	109.90 (12)	N1—C21—H21C	109.5
C6—C7—C8	109.47 (12)	H21A—C21—H21C	109.5
C10—C7—C8	107.78 (11)	H21B—C21—H21C	109.5
C9—C8—C12	115.51 (12)	N2—C22—H22A	109.5
C9—C8—C7	107.36 (12)	N2—C22—H22B	109.5
C12—C8—C7	108.51 (12)	H22A—C22—H22B	109.5
C9—C8—H8	108.4	N2—C22—H22C	109.5
C12—C8—H8	108.4	H22A—C22—H22C	109.5
C7—C8—H8	108.4	H22B—C22—H22C	109.5
C1—C9—C5	118.19 (15)	O5—C23—O6	123.51 (15)
C1—C9—C8	121.53 (14)	O5—C23—C7	124.85 (15)
C5—C9—C8	120.18 (13)	O6—C23—C7	111.63 (13)
O2—C10—C15	105.79 (12)	O6—C24—H24A	109.5
O2—C10—C7	109.87 (11)	O6—C24—H24B	109.5
C15—C10—C7	116.24 (12)	H24A—C24—H24B	109.5
O2—C10—H10	108.2	O6—C24—H24C	109.5
C15—C10—H10	108.2	H24A—C24—H24C	109.5
C7—C10—H10	108.2	H24B—C24—H24C	109.5
C12—C11—O2	125.41 (13)	C11—N1—C14	121.08 (15)
C12—C11—N1	123.77 (15)	C11—N1—C21	120.78 (15)
O2—C11—N1	110.80 (14)	C14—N1—C21	118.08 (15)
C11—C12—C13	117.48 (14)	C14—N2—C13	125.05 (15)
C11—C12—C8	120.89 (13)	C14—N2—C22	117.44 (17)
C13—C12—C8	121.44 (14)	C13—N2—C22	116.43 (18)
O4—C13—N2	119.60 (16)	C5—O1—C6	119.44 (12)
O4—C13—C12	124.74 (16)	C11—O2—C10	116.93 (12)
N2—C13—C12	115.66 (16)	C23—O6—C24	116.01 (16)
C9—C1—C2—C3	−2.2 (3)	O2—C10—C15—C20	−141.61 (15)
C1—C2—C3—C4	0.0 (3)	C7—C10—C15—C20	96.17 (18)
C2—C3—C4—C5	0.9 (3)	C20—C15—C16—C17	−0.8 (3)
C3—C4—C5—O1	−178.52 (17)	C10—C15—C16—C17	179.57 (16)
C3—C4—C5—C9	0.5 (3)	C15—C16—C17—C18	0.2 (3)
O1—C6—C7—C23	−68.32 (16)	C16—C17—C18—C19	0.1 (3)
O1—C6—C7—C10	171.38 (12)	C16—C17—C18—Cl1	−179.90 (16)
O1—C6—C7—C8	52.18 (16)	C17—C18—C19—C20	0.3 (3)
C23—C7—C8—C9	65.52 (15)	Cl1—C18—C19—C20	−179.69 (16)
C6—C7—C8—C9	−54.69 (15)	C18—C19—C20—C15	−1.0 (3)
C10—C7—C8—C9	−176.20 (11)	C16—C15—C20—C19	1.3 (3)
C23—C7—C8—C12	−169.00 (12)	C10—C15—C20—C19	−179.14 (17)
C6—C7—C8—C12	70.80 (14)	C6—C7—C23—O5	−1.3 (2)
C10—C7—C8—C12	−50.71 (15)	C10—C7—C23—O5	120.72 (18)
C2—C1—C9—C5	3.5 (3)	C8—C7—C23—O5	−121.56 (18)
C2—C1—C9—C8	179.82 (17)	C6—C7—C23—O6	179.19 (14)
O1—C5—C9—C1	176.26 (16)	C10—C7—C23—O6	−58.77 (17)
C4—C5—C9—C1	−2.7 (2)	C8—C7—C23—O6	58.96 (17)
O1—C5—C9—C8	−0.1 (2)	C12—C11—N1—C14	0.7 (3)
C4—C5—C9—C8	−178.98 (15)	O2—C11—N1—C14	−177.63 (15)
C12—C8—C9—C1	93.78 (18)	C12—C11—N1—C21	−176.51 (17)
C7—C8—C9—C1	−145.05 (15)	O2—C11—N1—C21	5.2 (2)
C12—C8—C9—C5	−90.03 (17)	O3—C14—N1—C11	178.87 (17)
C7—C8—C9—C5	31.15 (19)	N2—C14—N1—C11	−0.2 (2)
C23—C7—C10—O2	−178.60 (12)	O3—C14—N1—C21	−3.9 (3)
C6—C7—C10—O2	−57.87 (15)	N2—C14—N1—C21	177.04 (16)
C8—C7—C10—O2	62.33 (15)	O3—C14—N2—C13	173.81 (18)
C23—C7—C10—C15	−58.56 (16)	N1—C14—N2—C13	−7.1 (3)
C6—C7—C10—C15	62.17 (16)	O3—C14—N2—C22	6.2 (3)
C8—C7—C10—C15	−177.63 (12)	N1—C14—N2—C22	−174.76 (19)
O2—C11—C12—C13	−176.39 (15)	O4—C13—N2—C14	−167.39 (18)
N1—C11—C12—C13	5.6 (2)	C12—C13—N2—C14	13.1 (3)
O2—C11—C12—C8	−1.2 (2)	O4—C13—N2—C22	0.4 (3)
N1—C11—C12—C8	−179.28 (14)	C12—C13—N2—C22	−179.16 (18)
C9—C8—C12—C11	142.93 (15)	C9—C5—O1—C6	−6.3 (2)
C7—C8—C12—C11	22.38 (19)	C4—C5—O1—C6	172.70 (14)
C9—C8—C12—C13	−42.1 (2)	C7—C6—O1—C5	−21.03 (19)
C7—C8—C12—C13	−162.66 (14)	C12—C11—O2—C10	11.6 (2)
C11—C12—C13—O4	168.86 (17)	N1—C11—O2—C10	−170.11 (13)
C8—C12—C13—O4	−6.3 (3)	C15—C10—O2—C11	−168.67 (13)
C11—C12—C13—N2	−11.6 (2)	C7—C10—O2—C11	−42.47 (17)
C8—C12—C13—N2	173.23 (14)	O5—C23—O6—C24	−3.5 (3)
O2—C10—C15—C16	38.0 (2)	C7—C23—O6—C24	176.02 (19)
C7—C10—C15—C16	−84.24 (19)

Cg4 is the centroid of the C1–C5/C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O3i	0.93	2.44	3.349 (2)	166
C19—H19···Cg4ii	0.93	2.84	3.720 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C1–C5/C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O3i	0.93	2.44	3.349 (2)	166
C19—H19⋯Cg4ii	0.93	2.84	3.720 (3)	158

Symmetry codes: (i) ; (ii) .