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ISSN: 2056-9890

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

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[Alam, O., Imran, M. & Khan, S. A. (2005). Indian J. Heterocycl. Chem. 14, 293-296.]); Kappe (2000[Kappe, C. O. (2000). Acc. Chem. Res. 33, 879-888.]); Condon et al. (1993[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.]); Rovnyak et al. (1995[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.]); Leite et al. (2006[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.]); Sriram et al. (2006[Sriram, D., Yogeeswari, P. & Devakaram, R. V. (2006). Bioorg. Med. Chem. 14, 3113-3118.]). For related structures, see: Booysen et al. (2011[Booysen, I., Muhammed, I., Soares, A., Gerber, T., Hosten, E. & Betz, R. (2011). Acta Cryst. E67, o1592.]); Noroozi Pesyan et al. (2009[Noroozi Pesyan, N., Rastgar, S. & Hosseini, Y. (2009). Acta Cryst. E65, o1444.]).

[Scheme 1]

Experimental

Crystal data
  • C24H21ClN2O6

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.924, Tmax = 0.951

  • 29343 measured reflections

  • 7232 independent reflections

  • 4518 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

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

D—H⋯A D—H H⋯A DA 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[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


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.

Refinement top

H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic CH, C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for methine CH, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2, C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3.

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
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] 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
C24H21ClN2O6F(000) = 976
Mr = 468.88Dx = 1.413 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7610 reflections
a = 10.6177 (5) Åθ = 2.2–30.2°
b = 11.9973 (5) ŵ = 0.22 mm1
c = 17.5532 (8) ÅT = 295 K
β = 99.751 (2)°Block, colourless
V = 2203.69 (17) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer
7232 independent reflections
Radiation source: fine-focus sealed tube4518 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 0 pixels mm-1θmax = 31.7°, θmin = 2.1°
ω and ϕ scansh = 1515
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1517
Tmin = 0.924, Tmax = 0.951l = 2525
29343 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-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 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.60 e Å3
Crystal data top
C24H21ClN2O6V = 2203.69 (17) Å3
Mr = 468.88Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.6177 (5) ŵ = 0.22 mm1
b = 11.9973 (5) ÅT = 295 K
c = 17.5532 (8) Å0.30 × 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)
Tmin = 0.924, Tmax = 0.951Rint = 0.029
29343 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.158H-atom parameters constrained
S = 1.03Δρmax = 0.42 e Å3
7232 reflectionsΔρmin = 0.60 e Å3
301 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.76555 (18)0.06202 (16)0.37637 (10)0.0480 (4)
H10.75990.13890.38190.058*
C20.8645 (2)0.00508 (18)0.42011 (11)0.0568 (5)
H20.92680.04360.45360.068*
C30.87131 (19)0.10942 (17)0.41423 (11)0.0541 (5)
H30.93830.14800.44380.065*
C40.77967 (17)0.16628 (15)0.36499 (10)0.0459 (4)
H40.78370.24350.36160.055*
C50.68080 (14)0.10821 (13)0.32016 (9)0.0361 (3)
C60.47962 (14)0.12010 (12)0.23307 (8)0.0338 (3)
H6A0.40810.17060.23270.041*
H6B0.49060.10880.17990.041*
C70.44663 (14)0.00850 (12)0.26651 (8)0.0310 (3)
C80.56484 (14)0.06889 (12)0.27607 (8)0.0328 (3)
H80.54640.13550.30460.039*
C90.67411 (15)0.00706 (13)0.32418 (9)0.0351 (3)
C100.33697 (14)0.05058 (13)0.21285 (8)0.0338 (3)
H100.32400.12380.23500.041*
C110.49137 (15)0.10189 (13)0.13570 (9)0.0362 (3)
C120.58675 (15)0.10449 (13)0.19648 (9)0.0356 (3)
C130.70722 (17)0.15057 (14)0.18445 (11)0.0438 (4)
C140.6217 (2)0.16628 (16)0.04577 (11)0.0510 (4)
C150.21085 (14)0.00924 (13)0.19859 (9)0.0356 (3)
C160.18358 (16)0.09052 (16)0.14232 (10)0.0464 (4)
H160.24420.10900.11190.056*
C170.06716 (18)0.14441 (18)0.13101 (11)0.0529 (5)
H170.04930.19920.09320.063*
C180.02226 (16)0.11680 (17)0.17584 (11)0.0482 (4)
C190.00161 (17)0.03659 (19)0.23166 (12)0.0550 (5)
H190.05950.01880.26190.066*
C200.11761 (17)0.01751 (16)0.24245 (11)0.0483 (4)
H200.13390.07300.27980.058*
C210.3952 (2)0.13297 (19)0.00072 (10)0.0597 (5)
H21A0.36030.05920.00810.090*
H21B0.42180.15770.04750.090*
H21C0.33120.18280.01230.090*
C220.8425 (2)0.2140 (3)0.09356 (16)0.0834 (8)
H22A0.86590.17970.04860.125*
H22B0.90710.19900.13760.125*
H22C0.83480.29310.08570.125*
C230.40621 (15)0.02757 (14)0.34447 (9)0.0364 (3)
C240.3303 (3)0.0581 (2)0.44840 (13)0.0941 (10)
H24A0.31010.01840.45690.141*
H24B0.25470.10280.44610.141*
H24C0.39430.08350.49010.141*
N10.50522 (15)0.13185 (13)0.06206 (8)0.0447 (3)
N20.71979 (16)0.16862 (13)0.10700 (10)0.0523 (4)
O10.59218 (11)0.17168 (9)0.27413 (7)0.0444 (3)
O20.37171 (11)0.06736 (10)0.13744 (6)0.0408 (3)
O30.63502 (17)0.19131 (14)0.01960 (8)0.0738 (5)
O40.79552 (13)0.17313 (13)0.23567 (9)0.0621 (4)
O50.39933 (16)0.11577 (11)0.37358 (8)0.0623 (4)
O60.37805 (15)0.06763 (11)0.37639 (7)0.0581 (4)
Cl10.16887 (5)0.18537 (6)0.16129 (4)0.0765 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0536 (10)0.0389 (9)0.0480 (9)0.0044 (8)0.0018 (8)0.0048 (7)
C20.0545 (11)0.0559 (12)0.0523 (10)0.0036 (9)0.0128 (8)0.0078 (9)
C30.0480 (10)0.0566 (12)0.0523 (10)0.0083 (9)0.0069 (8)0.0013 (9)
C40.0447 (9)0.0387 (9)0.0527 (10)0.0080 (7)0.0033 (7)0.0013 (7)
C50.0350 (7)0.0340 (8)0.0392 (7)0.0002 (6)0.0056 (6)0.0032 (6)
C60.0363 (7)0.0289 (7)0.0357 (7)0.0003 (6)0.0046 (6)0.0008 (6)
C70.0342 (7)0.0277 (7)0.0316 (6)0.0001 (5)0.0076 (5)0.0014 (5)
C80.0373 (7)0.0258 (7)0.0356 (7)0.0010 (6)0.0074 (6)0.0005 (5)
C90.0371 (8)0.0309 (8)0.0369 (7)0.0015 (6)0.0050 (6)0.0003 (6)
C100.0382 (7)0.0314 (8)0.0327 (7)0.0036 (6)0.0089 (6)0.0025 (6)
C110.0462 (8)0.0288 (8)0.0361 (7)0.0018 (6)0.0142 (6)0.0033 (6)
C120.0397 (8)0.0287 (7)0.0407 (8)0.0012 (6)0.0135 (6)0.0025 (6)
C130.0435 (9)0.0366 (9)0.0549 (10)0.0011 (7)0.0191 (8)0.0027 (7)
C140.0686 (12)0.0424 (10)0.0490 (10)0.0040 (8)0.0307 (9)0.0009 (8)
C150.0343 (7)0.0363 (8)0.0360 (7)0.0054 (6)0.0057 (6)0.0018 (6)
C160.0396 (8)0.0580 (11)0.0432 (9)0.0004 (8)0.0113 (7)0.0102 (8)
C170.0461 (10)0.0610 (12)0.0499 (10)0.0055 (8)0.0037 (8)0.0112 (9)
C180.0334 (8)0.0594 (12)0.0504 (9)0.0006 (7)0.0030 (7)0.0066 (8)
C190.0386 (9)0.0707 (13)0.0592 (11)0.0044 (9)0.0179 (8)0.0048 (10)
C200.0430 (9)0.0516 (11)0.0526 (10)0.0039 (8)0.0149 (8)0.0100 (8)
C210.0799 (14)0.0630 (13)0.0364 (9)0.0073 (11)0.0098 (9)0.0083 (8)
C220.0676 (15)0.099 (2)0.0960 (18)0.0118 (13)0.0491 (14)0.0139 (15)
C230.0387 (8)0.0362 (8)0.0351 (7)0.0014 (6)0.0086 (6)0.0029 (6)
C240.159 (3)0.0829 (18)0.0556 (13)0.0290 (18)0.0609 (16)0.0027 (12)
N10.0588 (9)0.0422 (8)0.0361 (7)0.0027 (7)0.0168 (6)0.0048 (6)
N20.0549 (9)0.0483 (9)0.0621 (10)0.0012 (7)0.0342 (8)0.0029 (7)
O10.0370 (6)0.0292 (6)0.0629 (7)0.0029 (4)0.0030 (5)0.0083 (5)
O20.0430 (6)0.0459 (7)0.0333 (5)0.0026 (5)0.0057 (4)0.0076 (5)
O30.1000 (12)0.0798 (11)0.0528 (8)0.0023 (9)0.0455 (8)0.0096 (7)
O40.0462 (7)0.0716 (10)0.0697 (9)0.0159 (7)0.0130 (7)0.0056 (7)
O50.0981 (11)0.0404 (8)0.0562 (8)0.0018 (7)0.0359 (8)0.0126 (6)
O60.0926 (11)0.0442 (7)0.0451 (7)0.0092 (7)0.0330 (7)0.0009 (5)
Cl10.0427 (3)0.1053 (5)0.0794 (4)0.0208 (3)0.0046 (2)0.0005 (3)
Geometric parameters (Å, º) top
C1—C21.374 (3)C13—N21.405 (2)
C1—C91.384 (2)C14—O31.217 (2)
C1—H10.9300C14—N21.364 (3)
C2—C31.380 (3)C14—N11.379 (2)
C2—H20.9300C15—C161.383 (2)
C3—C41.369 (3)C15—C201.391 (2)
C3—H30.9300C16—C171.379 (3)
C4—C51.388 (2)C16—H160.9300
C4—H40.9300C17—C181.372 (3)
C5—O11.3639 (18)C17—H170.9300
C5—C91.387 (2)C18—C191.366 (3)
C6—O11.4280 (18)C18—Cl11.7408 (18)
C6—C71.526 (2)C19—C201.377 (3)
C6—H6A0.9700C19—H190.9300
C6—H6B0.9700C20—H200.9300
C7—C231.519 (2)C21—N11.464 (2)
C7—C101.541 (2)C21—H21A0.9600
C7—C81.547 (2)C21—H21B0.9600
C8—C91.509 (2)C21—H21C0.9600
C8—C121.516 (2)C22—N21.468 (2)
C8—H80.9800C22—H22A0.9600
C10—O21.4471 (17)C22—H22B0.9600
C10—C151.502 (2)C22—H22C0.9600
C10—H100.9800C23—O51.183 (2)
C11—C121.341 (2)C23—O61.328 (2)
C11—O21.3416 (19)C24—O61.444 (2)
C11—N11.3734 (19)C24—H24A0.9600
C12—C131.442 (2)C24—H24B0.9600
C13—O41.214 (2)C24—H24C0.9600
C2—C1—C9121.17 (17)O3—C14—N2122.88 (19)
C2—C1—H1119.4O3—C14—N1121.4 (2)
C9—C1—H1119.4N2—C14—N1115.75 (15)
C1—C2—C3119.86 (17)C16—C15—C20118.39 (16)
C1—C2—H2120.1C16—C15—C10121.91 (14)
C3—C2—H2120.1C20—C15—C10119.70 (15)
C4—C3—C2120.16 (17)C17—C16—C15120.49 (16)
C4—C3—H3119.9C17—C16—H16119.8
C2—C3—H3119.9C15—C16—H16119.8
C3—C4—C5119.75 (17)C18—C17—C16119.64 (18)
C3—C4—H4120.1C18—C17—H17120.2
C5—C4—H4120.1C16—C17—H17120.2
O1—C5—C9123.41 (14)C19—C18—C17121.26 (17)
O1—C5—C4115.80 (15)C19—C18—Cl1119.39 (14)
C9—C5—C4120.79 (15)C17—C18—Cl1119.35 (15)
O1—C6—C7114.40 (12)C18—C19—C20118.93 (17)
O1—C6—H6A108.7C18—C19—H19120.5
C7—C6—H6A108.7C20—C19—H19120.5
O1—C6—H6B108.7C19—C20—C15121.28 (17)
C7—C6—H6B108.7C19—C20—H20119.4
H6A—C6—H6B107.6C15—C20—H20119.4
C23—C7—C6109.42 (12)N1—C21—H21A109.5
C23—C7—C10108.69 (12)N1—C21—H21B109.5
C6—C7—C10111.56 (12)H21A—C21—H21B109.5
C23—C7—C8109.90 (12)N1—C21—H21C109.5
C6—C7—C8109.47 (12)H21A—C21—H21C109.5
C10—C7—C8107.78 (11)H21B—C21—H21C109.5
C9—C8—C12115.51 (12)N2—C22—H22A109.5
C9—C8—C7107.36 (12)N2—C22—H22B109.5
C12—C8—C7108.51 (12)H22A—C22—H22B109.5
C9—C8—H8108.4N2—C22—H22C109.5
C12—C8—H8108.4H22A—C22—H22C109.5
C7—C8—H8108.4H22B—C22—H22C109.5
C1—C9—C5118.19 (15)O5—C23—O6123.51 (15)
C1—C9—C8121.53 (14)O5—C23—C7124.85 (15)
C5—C9—C8120.18 (13)O6—C23—C7111.63 (13)
O2—C10—C15105.79 (12)O6—C24—H24A109.5
O2—C10—C7109.87 (11)O6—C24—H24B109.5
C15—C10—C7116.24 (12)H24A—C24—H24B109.5
O2—C10—H10108.2O6—C24—H24C109.5
C15—C10—H10108.2H24A—C24—H24C109.5
C7—C10—H10108.2H24B—C24—H24C109.5
C12—C11—O2125.41 (13)C11—N1—C14121.08 (15)
C12—C11—N1123.77 (15)C11—N1—C21120.78 (15)
O2—C11—N1110.80 (14)C14—N1—C21118.08 (15)
C11—C12—C13117.48 (14)C14—N2—C13125.05 (15)
C11—C12—C8120.89 (13)C14—N2—C22117.44 (17)
C13—C12—C8121.44 (14)C13—N2—C22116.43 (18)
O4—C13—N2119.60 (16)C5—O1—C6119.44 (12)
O4—C13—C12124.74 (16)C11—O2—C10116.93 (12)
N2—C13—C12115.66 (16)C23—O6—C24116.01 (16)
C9—C1—C2—C32.2 (3)O2—C10—C15—C20141.61 (15)
C1—C2—C3—C40.0 (3)C7—C10—C15—C2096.17 (18)
C2—C3—C4—C50.9 (3)C20—C15—C16—C170.8 (3)
C3—C4—C5—O1178.52 (17)C10—C15—C16—C17179.57 (16)
C3—C4—C5—C90.5 (3)C15—C16—C17—C180.2 (3)
O1—C6—C7—C2368.32 (16)C16—C17—C18—C190.1 (3)
O1—C6—C7—C10171.38 (12)C16—C17—C18—Cl1179.90 (16)
O1—C6—C7—C852.18 (16)C17—C18—C19—C200.3 (3)
C23—C7—C8—C965.52 (15)Cl1—C18—C19—C20179.69 (16)
C6—C7—C8—C954.69 (15)C18—C19—C20—C151.0 (3)
C10—C7—C8—C9176.20 (11)C16—C15—C20—C191.3 (3)
C23—C7—C8—C12169.00 (12)C10—C15—C20—C19179.14 (17)
C6—C7—C8—C1270.80 (14)C6—C7—C23—O51.3 (2)
C10—C7—C8—C1250.71 (15)C10—C7—C23—O5120.72 (18)
C2—C1—C9—C53.5 (3)C8—C7—C23—O5121.56 (18)
C2—C1—C9—C8179.82 (17)C6—C7—C23—O6179.19 (14)
O1—C5—C9—C1176.26 (16)C10—C7—C23—O658.77 (17)
C4—C5—C9—C12.7 (2)C8—C7—C23—O658.96 (17)
O1—C5—C9—C80.1 (2)C12—C11—N1—C140.7 (3)
C4—C5—C9—C8178.98 (15)O2—C11—N1—C14177.63 (15)
C12—C8—C9—C193.78 (18)C12—C11—N1—C21176.51 (17)
C7—C8—C9—C1145.05 (15)O2—C11—N1—C215.2 (2)
C12—C8—C9—C590.03 (17)O3—C14—N1—C11178.87 (17)
C7—C8—C9—C531.15 (19)N2—C14—N1—C110.2 (2)
C23—C7—C10—O2178.60 (12)O3—C14—N1—C213.9 (3)
C6—C7—C10—O257.87 (15)N2—C14—N1—C21177.04 (16)
C8—C7—C10—O262.33 (15)O3—C14—N2—C13173.81 (18)
C23—C7—C10—C1558.56 (16)N1—C14—N2—C137.1 (3)
C6—C7—C10—C1562.17 (16)O3—C14—N2—C226.2 (3)
C8—C7—C10—C15177.63 (12)N1—C14—N2—C22174.76 (19)
O2—C11—C12—C13176.39 (15)O4—C13—N2—C14167.39 (18)
N1—C11—C12—C135.6 (2)C12—C13—N2—C1413.1 (3)
O2—C11—C12—C81.2 (2)O4—C13—N2—C220.4 (3)
N1—C11—C12—C8179.28 (14)C12—C13—N2—C22179.16 (18)
C9—C8—C12—C11142.93 (15)C9—C5—O1—C66.3 (2)
C7—C8—C12—C1122.38 (19)C4—C5—O1—C6172.70 (14)
C9—C8—C12—C1342.1 (2)C7—C6—O1—C521.03 (19)
C7—C8—C12—C13162.66 (14)C12—C11—O2—C1011.6 (2)
C11—C12—C13—O4168.86 (17)N1—C11—O2—C10170.11 (13)
C8—C12—C13—O46.3 (3)C15—C10—O2—C11168.67 (13)
C11—C12—C13—N211.6 (2)C7—C10—O2—C1142.47 (17)
C8—C12—C13—N2173.23 (14)O5—C23—O6—C243.5 (3)
O2—C10—C15—C1638.0 (2)C7—C23—O6—C24176.02 (19)
C7—C10—C15—C1684.24 (19)
Hydrogen-bond geometry (Å, º) top
Cg4 is the centroid of the C1–C5/C9 ring.
D—H···AD—HH···AD···AD—H···A
C16—H16···O3i0.932.443.349 (2)166
C19—H19···Cg4ii0.932.843.720 (3)158
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC24H21ClN2O6
Mr468.88
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)10.6177 (5), 11.9973 (5), 17.5532 (8)
β (°) 99.751 (2)
V3)2203.69 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.924, 0.951
No. of measured, independent and
observed [I > 2σ(I)] reflections
29343, 7232, 4518
Rint0.029
(sin θ/λ)max1)0.739
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.158, 1.03
No. of reflections7232
No. of parameters301
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C16—H16···O3i0.932.443.349 (2)166
C19—H19···Cg4ii0.932.843.720 (3)158
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
 

References

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First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCondon, 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.
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First citationRovnyak, 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
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
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