Methyl 6-(4-chloro­phen­yl)-2,4-dimethyl-1,3-dioxo-1,2,3,4,6,6a,7,12b-octa­hydro­chromeno[4′,3′:4,5]pyrano[2,3-d]pyrimidine-6a-carboxyl­ate

Kanchanadevi, J.; Anbalagan, G.; Sivakumar, G.; Bakthadoss, M.; Manivannan, V.

doi:10.1107/S160053681102678X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1990

doi:10.1107/S160053681102678X

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Methyl 6-(4-chlorophenyl)-2,4-dimethyl-1,3-dioxo-1,2,3,4,6,6a,7,12b-octahydrochromeno[4′,3′:4,5]pyrano[2,3-d]pyrimidine-6a-carboxylate

J. Kanchanadevi,^a G. Anbalagan,^b G. Sivakumar,^c M. Bakthadoss ^c and V. Manivannan ^d ^*

^aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601 204, India, ^bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^cDepartment of Organic Chemistry, University of Madras, Maraimalai campus, Chennai 600 025, India, and ^dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: crystallography2010@gmail.com, phdguna@gmail.com

(Received 23 June 2011; accepted 5 July 2011; online 9 July 2011)

In the title compound, C₂₄H₂₁ClN₂O₆, the two fused six-membered pyran rings adopt half-chair conformations. The dihedral angle between the pyrimidine ring and the chlorophenyl ring is 51.55 (3)°. In the crystal, molecules are linked by pairs of weak intermolecular C—H⋯O hydrogen bonds, forming inversion dimers. A C—H⋯π interaction 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_r = 468.88
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.158
S = 1.03
7232 reflections
301 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.60 e Å⁻³

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) -x+1, -y, -z; (ii) x-1, y, z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681102678X/is2742sup1.cif

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

Supporting information file. DOI: 10.1107/S160053681102678X/is2742Isup3.cml

checkCIF report

Comment top

Pyrimidine derivatives are used in the areas of pesticide and pharmaceutical agents (Condon et al., 1993). In addition, pyrimidine-2(1H)-ones/thiones are calcium channel blocker compounds (Rovnyak et al., 1995). They also have other biological activities such as antibacterial, antifungal and antiviral (Kappe, 2000; Alam et al., 2005; Sriram et al., 2006; Leite et al., 2006).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Booysen et al., 2011; Noroozi Pesyan et al., 2009). The sum of bond angles around N1 and N2 [359.93 (15) and 358.92°, respectively] indicates the sp² hybridization state of atoms N1 and N2 in the molecule. The crystal packing is controlled by weak intermolecular C—H···O and C—H···π interactions (Table 1).

Related literature top

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 top

A mixture of (E)-methyl 2-((2-formylphenoxy)methyl)-3-(4-chlorophenyl)acrylate (0.330 g, 1 mmol) and N,N-dimethylbarbutric acid (0.156 g, 1 mmol) was placed in a round bottom flask and melted at 180 °C for 1 h. After completion of the reaction as indicated by TLC, the crude product was washed with 5 ml of ethylacetate and hexane mixture (1:49 ratio) which successfully provided the pure product methyl-6-(4-chlorophenyl)-2,4-dimethyl-1,3-dioxo- 1,2,3,4,6,6a,7,12octahydrochromeno[4',3',4,5]pyrano[2,3-d]pyrimidine- 6a-carboxylate, as colorless solid in 96% yield.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A packing diagram of the title compound, viewed down the b axis. Hydrogen bonds are shown as dashed lines.

Methyl 6-(4-chlorophenyl)-2,4-dimethyl-1,3-dioxo-1,2,3,4,6,6a,7,12b- octahydrochromeno[4',3':4,5]pyrano[2,3-d]pyrimidine-6a-carboxylate top

Crystal data top

C₂₄H₂₁ClN₂O₆	F(000) = 976
M_r = 468.88	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	7232 independent reflections
Radiation source: fine-focus sealed tube	4518 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 0 pixels mm^-1	θ_max = 31.7°, θ_min = 2.1°
ω and ϕ scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −15→17
T_min = 0.924, T_max = 0.951	l = −25→25
29343 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0706P)² + 0.6194P] where P = (F_o² + 2F_c²)/3
7232 reflections	(Δ/σ)_max = 0.005
301 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

C₂₄H₂₁ClN₂O₆	V = 2203.69 (17) Å³
M_r = 468.88	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6177 (5) Å	µ = 0.22 mm⁻¹
b = 11.9973 (5) Å	T = 295 K
c = 17.5532 (8) Å	0.30 × 0.25 × 0.20 mm
β = 99.751 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	7232 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4518 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.951	R_int = 0.029
29343 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.03	Δρ_max = 0.42 e Å⁻³
7232 reflections	Δρ_min = −0.60 e Å⁻³
301 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₁ClN₂O₆
M_r	468.88
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.6177 (5), 11.9973 (5), 17.5532 (8)
β (°)	99.751 (2)
V (Å³)	2203.69 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.924, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	29343, 7232, 4518
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.739

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.158, 1.03
No. of reflections	7232
No. of parameters	301
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.60

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z; (ii) x−1, y, z.

References

Alam, O., Imran, M. & Khan, S. A. (2005). Indian J. Heterocycl. Chem. 14, 293–296. CAS Google Scholar
Booysen, I., Muhammed, I., Soares, A., Gerber, T., Hosten, E. & Betz, R. (2011). Acta Cryst. E67, o1592. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Condon, M. E., Brady, T. E., Feist, D., Malefyt, T., Marc, P., Quakenbush, L. S., Rodaway, S. J., Shaner, D. L. & Tecle, B. (1993). Brighton Crop Protection Conference–Weeds, pp. 41–46. Google Scholar
Kappe, C. O. (2000). Acc. Chem. Res. 33, 879–888. Web of Science CrossRef PubMed CAS Google Scholar
Leite, A. C. L., Lima, R. S., Moreira, D. R. M., Cardoso, M. V. O., Brito, A. C. G., Santos, L. M. F., Hernandes, M. Z., Kiperstok, A. C., Lima, R. S. & Soares, M. B. P. (2006). Bioorg. Med. Chem. 14, 3749–3757. Web of Science CrossRef PubMed CAS Google Scholar
Noroozi Pesyan, N., Rastgar, S. & Hosseini, Y. (2009). Acta Cryst. E65, o1444. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rovnyak, G. C., Kimball, S. D., Beyer, B., Cucinotta, G., DiMarco, J. D., Gougoutas, J., Hedberg, A., Malley, M., McCarthy, J. P., Zhang, R. & Moreland, S. (1995). J. Med. Chem. 38, 119–129. CSD CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 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
Sriram, D., Yogeeswari, P. & Devakaram, R. V. (2006). Bioorg. Med. Chem. 14, 3113–3118. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 67| Part 8| August 2011| Page o1990

doi:10.1107/S160053681102678X

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

Methyl 6-(4-chloro­phen­yl)-2,4-di­methyl-1,3-dioxo-1,2,3,4,6,6a,7,12b-octa­hydro­chromeno[4′,3′:4,5]pyrano[2,3-d]pyrimidine-6a-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

Methyl 6-(4-chlorophenyl)-2,4-dimethyl-1,3-dioxo-1,2,3,4,6,6a,7,12b-octahydrochromeno[4′,3′:4,5]pyrano[2,3-d]pyrimidine-6a-carboxylate