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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2673
https://doi.org/10.1107/S1600536811037196

Methyl rac-(2R,11S,12R)-12-(2-chloro­phen­yl)-22-oxo-9,13,21-trioxa­penta­cyclo­[12.8.0.02,11.03,8.015,20]docosa-1(14),3,5,7,15(20),16,18-hepta­ene-11-carboxyl­ate

K. Swaminathan,a K. Sethusankar,a* G. Sivakumarb and M. Bakthadossb

aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 20 August 2011; accepted 13 September 2011; online 17 September 2011)

In the title compound C27H19ClO6, the coumarin ring system is not exactly planar, with a dihedral angle of 4.12 (7)° between its benzene and lactone rings. The cis-fused pyran rings adopt half-chair conformations. The carbometh­oxy and chloro­phenyl groups are in a trans configuration. The crystal packing is stabilized by inter­molecular C—H⋯O interactions, which produce a centrosymmetric R22(14) dimer and two centrosymmetric R22(18) dimers connecting the mol­ecules in a two-dimensional fashion.

Related literature

For uses of coumarins, see: Kayser & Kolodziej (1997[Kayser, O. & Kolodziej, H. (1997). Planta Med. 63, 508-510.]); Fan et al. (2001[Fan, G. J., Mar, W., Park, M. K., Wook Choi, E., Kim, K. & Kim, S. (2001). Bioorg. Med. Chem. Lett. 11, 2361-2363.]); Wang et al. (2002[Wang, C. J., Hsieh, Y. J., Chu, C. Y., Lin, Y. L. & Tseng, T. H. (2002). Cancer Lett. 183, 163-168.]). For related structures, see: Kanchanadevi et al. (2011[Kanchanadevi, J., Anbalagan, G., Sivakumar, G., Bakthadoss, M. & Manivannan, V. (2011). Acta Cryst. E67, o1990.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C27H19ClO6

  • Mr = 474.87

  • Triclinic, [P \overline 1]

  • a = 8.4441 (3) Å

  • b = 9.7556 (3) Å

  • c = 13.8546 (5) Å

  • α = 73.831 (2)°

  • β = 82.858 (2)°

  • γ = 87.962 (2)°

  • V = 1087.65 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 293 K

  • 0.30 × 0.25 × 0.25 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • 26685 measured reflections

  • 6336 independent reflections

  • 4968 reflections with I > 2σ(I)

  • Rint = 0.026
Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.143

  • S = 1.01

  • 6336 reflections

  • 308 parameters

  • H-atom parameters constrained

  • Δρmax = 0.57 e Å−3

  • Δρmin = −0.52 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2⋯O5i 0.93 2.59 3.271 (2) 130
C12—H12⋯O4ii 0.98 2.53 3.3316 (16) 139
C23—H23⋯O5iii 0.93 2.47 3.355 (3) 159
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z; (iii) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811037196/ld2025sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037196/ld2025Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811037196/ld2025Isup3.cml

checkCIF report


Comment top

The title compound C27H19Cl O6 was synthesized using domino Knoevenagel intramolecular hetero-Diels-Alder reaction, used extensively in the synthesis of heterocyclic and polycyclic compounds. Coumarin derivatives find applications as active components in pesticides and additives in the manufacture of pharmaceuticals and cosmetics. They are also known to posses antibacterial (Kayser & Kolodziej, 1997), anticancer (Wang et al., 2002) and steroid 5a-reductase inhibitory (Fan et al., 2001) activities.

The title compound C27H19ClO6 comprises a chromene ring and a coumarin ring fused to alternate sides of a pyran ring. A chlorobenzene ring and a carboxylate group are also trans-attached to the same pyran ring in adjacent positions. The X-ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig.1.

The chlorine atom Cl1 deviates from the least square plane of the phenyl ring (C20-C25) by 0.0568 Å and the deviation of atom O4 from the least square plane of the coumarin ring (O3,C10,C11,C13-C19) is 0.3315 (12) Å. Also, the dihedral angle between the least square planes of the pyran ring (O2,C8-C12) and the carboxylate side chain is 56.47 (6)°. The title compound exhibits sturctural similarities with a reported structure (Kanchanadevi et al., 2011).

The crystal packing is stabilized by C—H..O intermolecular ineractions, which include a R22(14) dimer and two R22(18) dimers formed through a bifurcated hydrogen bond between a carboxylate O atom and two C atoms, one each from the nearby chromene and chlorobenzene rings, respectively (Bernstein et al.. 1995). (Table 1). The symmetry codes are: (i) 1 - x,1 - y,1 - z; (ii) 1 - x,1 - y,-z and (iii) -x,-y,1 - z. The packing arrangement of the title compound is shown in Fig.2.

Related literature top

For uses of coumarins, see: Kayser & Kolodziej (1997); Fan et al. (2001); Wang et al. (2002). For related structures, see: Kanchanadevi et al. (2011). For puckering parameters, see: Cremer & Pople (1975). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

A mixture of (E)-methyl 2-((2-formylphenoxy)methyl)-3-(2-chlorophenyl) acrylate (0.330 g, 1 mmol) and 4-hydroxy-2H-chromen-2-one (0.162 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:hexane mixture (1:49 ratio) which successfully provided the pure product, methyl rac-(2R,11S,12R)- 12-(2-chlorophenyl)-22-oxo-9,13,21-trioxapentacyclo [12.8.0.02,11.03,8.015,20]docosa-1(14),3,5,7,15 (20),16,18- heptaene-11-carboxylate, as colourless solid in 92% yield.

Refinement top

Positions of hydrogen atoms were localized from the difference electron density maps and their distances were geometically constrained. The hydrogen atoms bound to the C atoms were treated as riding atoms, with d(C—H)=0.93 Å and Uiso(H)=1.2Ueq(C) for aromatic, d(C—H)=0.98 Å and Uiso(H)=1.2Ueq(C) for methyne, d(C—H)=0.97 Å and Uiso(H)=1.2Ueq(C) for methylene and d(C—H)=0.96 Å and Uiso(H)=1.5Ueq(C) for methyl groups. The rotation angles for methyl group were optimized by least squares.

Structure description top

The title compound C27H19Cl O6 was synthesized using domino Knoevenagel intramolecular hetero-Diels-Alder reaction, used extensively in the synthesis of heterocyclic and polycyclic compounds. Coumarin derivatives find applications as active components in pesticides and additives in the manufacture of pharmaceuticals and cosmetics. They are also known to posses antibacterial (Kayser & Kolodziej, 1997), anticancer (Wang et al., 2002) and steroid 5a-reductase inhibitory (Fan et al., 2001) activities.

The title compound C27H19ClO6 comprises a chromene ring and a coumarin ring fused to alternate sides of a pyran ring. A chlorobenzene ring and a carboxylate group are also trans-attached to the same pyran ring in adjacent positions. The X-ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig.1.

The chlorine atom Cl1 deviates from the least square plane of the phenyl ring (C20-C25) by 0.0568 Å and the deviation of atom O4 from the least square plane of the coumarin ring (O3,C10,C11,C13-C19) is 0.3315 (12) Å. Also, the dihedral angle between the least square planes of the pyran ring (O2,C8-C12) and the carboxylate side chain is 56.47 (6)°. The title compound exhibits sturctural similarities with a reported structure (Kanchanadevi et al., 2011).

The crystal packing is stabilized by C—H..O intermolecular ineractions, which include a R22(14) dimer and two R22(18) dimers formed through a bifurcated hydrogen bond between a carboxylate O atom and two C atoms, one each from the nearby chromene and chlorobenzene rings, respectively (Bernstein et al.. 1995). (Table 1). The symmetry codes are: (i) 1 - x,1 - y,1 - z; (ii) 1 - x,1 - y,-z and (iii) -x,-y,1 - z. The packing arrangement of the title compound is shown in Fig.2.

For uses of coumarins, see: Kayser & Kolodziej (1997); Fan et al. (2001); Wang et al. (2002). For related structures, see: Kanchanadevi et al. (2011). For puckering parameters, see: Cremer & Pople (1975). For graph-set notation, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are present as small spheres of arbitary radius.
[Figure 2] Fig. 2. Part of the crystal structure of the title compound viewed down c axis, showing the formation of R22(14) and R22(18) dimers. C—H···O intermolecular interactions are indicated by dashed lines. Symmetry code: (i) 1 - x,1 - y,1 - z; (ii) 1 - x,1 - y,-z and (iii) -x,-y,1 - z.
Methyl rac-(2R,11S,12R)-12-(2-chlorophenyl)- 22-oxo-9,13,21-trioxapentacyclo[12.8.0.02,11.03,8.015,20]docosa- 1(14),3,5,7,15(20),16,18-heptaene-11-carboxylate top
Crystal data top
C27H19ClO6Z = 2
Mr = 474.87F(000) = 492
Triclinic, P1Dx = 1.450 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4441 (3) ÅCell parameters from 6336 reflections
b = 9.7556 (3) Åθ = 2.2–30.0°
c = 13.8546 (5) ŵ = 0.22 mm−1
α = 73.831 (2)°T = 293 K
β = 82.858 (2)°Block, colourless
γ = 87.962 (2)°0.30 × 0.25 × 0.25 mm
V = 1087.65 (6) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer		4968 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 30.0°, θmin = 2.2°
ω scansh = −11→11
26685 measured reflectionsk = −12→13
6336 independent reflectionsl = −19→19
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0742P)2 + 0.3227P]
where P = (Fo2 + 2Fc2)/3
6336 reflections(Δ/σ)max < 0.001
308 parametersΔρmax = 0.57 e Å−3
0 restraintsΔρmin = −0.52 e Å−3
Crystal data top
C27H19ClO6γ = 87.962 (2)°
Mr = 474.87V = 1087.65 (6) Å3
Triclinic, P1Z = 2
a = 8.4441 (3) ÅMo Kα radiation
b = 9.7556 (3) ŵ = 0.22 mm−1
c = 13.8546 (5) ÅT = 293 K
α = 73.831 (2)°0.30 × 0.25 × 0.25 mm
β = 82.858 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer		4968 reflections with I > 2σ(I)
26685 measured reflectionsRint = 0.026
6336 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 1.01Δρmax = 0.57 e Å−3
6336 reflectionsΔρmin = −0.52 e Å−3
308 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.65779 (17)0.56358 (17)0.40142 (11)0.0427 (3)
H10.67840.51990.46740.051*
C20.6817 (2)0.70748 (18)0.36081 (13)0.0485 (4)
H20.71990.76120.39890.058*
C30.6491 (2)0.77270 (17)0.26310 (13)0.0493 (4)
H30.66740.86990.23490.059*
C40.58945 (19)0.69331 (15)0.20757 (11)0.0424 (3)
H40.56320.73890.14310.051*
C50.56753 (15)0.54613 (14)0.24582 (9)0.0331 (3)
C60.60257 (15)0.48263 (14)0.34399 (10)0.0345 (3)
C70.51941 (16)0.25398 (14)0.33923 (10)0.0355 (3)
H7A0.46680.17160.38740.043*
H7B0.60780.21970.30040.043*
C80.40116 (14)0.33317 (13)0.26765 (9)0.0302 (2)
C90.48878 (14)0.45976 (13)0.18856 (9)0.0301 (2)
H90.40880.52050.15150.036*
C100.59876 (14)0.40135 (13)0.11382 (9)0.0311 (2)
C110.58170 (14)0.26821 (14)0.10487 (9)0.0323 (2)
C120.33567 (14)0.23433 (14)0.21156 (9)0.0322 (2)
H120.26960.29120.16140.039*
C130.71735 (16)0.49406 (15)0.04264 (9)0.0369 (3)
C140.81399 (16)0.29644 (16)−0.01975 (10)0.0391 (3)
C150.68874 (15)0.21021 (15)0.03630 (9)0.0347 (3)
C160.67418 (18)0.07365 (17)0.02455 (11)0.0432 (3)
H160.59070.01460.06150.052*
C170.7832 (2)0.0264 (2)−0.04158 (14)0.0546 (4)
H170.7722−0.0637−0.05050.066*
C180.9098 (2)0.1137 (2)−0.09498 (14)0.0590 (4)
H180.98410.0806−0.13870.071*
C190.92701 (19)0.2478 (2)−0.08424 (12)0.0531 (4)
H191.01280.3051−0.11950.064*
C200.23943 (16)0.10893 (14)0.27860 (10)0.0362 (3)
C210.3141 (2)−0.01302 (16)0.33065 (13)0.0484 (4)
H210.4247−0.01980.32030.058*
C220.2274 (3)−0.12563 (19)0.39802 (15)0.0646 (5)
H220.2798−0.20620.43310.078*
C230.0635 (3)−0.1172 (2)0.41250 (16)0.0699 (6)
H230.0051−0.19160.45840.084*
C24−0.0138 (2)−0.0002 (2)0.35981 (15)0.0619 (5)
H24−0.12460.00450.36900.074*
C250.07359 (17)0.11175 (18)0.29258 (12)0.0454 (3)
C260.26076 (15)0.38165 (15)0.33110 (10)0.0352 (3)
C270.0578 (3)0.5498 (3)0.33678 (18)0.0788 (7)
H27A−0.03350.49410.33630.118*
H27B0.03790.64860.30490.118*
H27C0.07710.53840.40540.118*
O10.57971 (13)0.34145 (11)0.39277 (7)0.0437 (2)
O20.46794 (11)0.17495 (10)0.15960 (7)0.0386 (2)
O30.82713 (12)0.43425 (12)−0.01572 (8)0.0439 (2)
O40.72725 (15)0.62092 (12)0.02839 (8)0.0514 (3)
O50.21355 (14)0.31564 (13)0.41573 (8)0.0511 (3)
O60.19620 (14)0.50185 (13)0.28202 (9)0.0556 (3)
Cl1−0.03104 (5)0.25730 (6)0.22616 (5)0.07724 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0385 (7)0.0535 (8)0.0382 (7)−0.0064 (6)−0.0058 (5)−0.0149 (6)
C20.0478 (8)0.0524 (9)0.0516 (8)−0.0101 (7)−0.0021 (6)−0.0251 (7)
C30.0576 (9)0.0389 (7)0.0524 (9)−0.0087 (6)0.0015 (7)−0.0165 (6)
C40.0510 (8)0.0350 (7)0.0385 (7)−0.0050 (6)−0.0011 (6)−0.0068 (5)
C50.0313 (6)0.0350 (6)0.0319 (6)−0.0047 (5)−0.0005 (4)−0.0081 (5)
C60.0290 (5)0.0388 (6)0.0342 (6)−0.0039 (5)−0.0029 (4)−0.0076 (5)
C70.0352 (6)0.0341 (6)0.0331 (6)−0.0027 (5)−0.0057 (5)−0.0017 (5)
C80.0277 (5)0.0324 (6)0.0271 (5)−0.0046 (4)−0.0006 (4)−0.0034 (4)
C90.0291 (5)0.0307 (5)0.0274 (5)−0.0034 (4)−0.0031 (4)−0.0028 (4)
C100.0285 (5)0.0365 (6)0.0255 (5)−0.0065 (4)−0.0017 (4)−0.0036 (4)
C110.0286 (5)0.0379 (6)0.0276 (5)−0.0062 (5)−0.0005 (4)−0.0050 (5)
C120.0282 (5)0.0355 (6)0.0307 (6)−0.0062 (4)0.0013 (4)−0.0070 (5)
C130.0361 (6)0.0446 (7)0.0270 (5)−0.0118 (5)−0.0015 (5)−0.0046 (5)
C140.0335 (6)0.0520 (8)0.0312 (6)−0.0056 (5)−0.0007 (5)−0.0109 (5)
C150.0317 (6)0.0432 (7)0.0285 (5)−0.0025 (5)−0.0029 (4)−0.0090 (5)
C160.0424 (7)0.0480 (8)0.0405 (7)−0.0034 (6)−0.0032 (6)−0.0149 (6)
C170.0566 (9)0.0605 (10)0.0527 (9)0.0029 (8)−0.0030 (7)−0.0275 (8)
C180.0516 (9)0.0769 (12)0.0530 (9)0.0047 (8)0.0062 (7)−0.0312 (9)
C190.0396 (7)0.0755 (11)0.0428 (8)−0.0071 (7)0.0084 (6)−0.0190 (8)
C200.0349 (6)0.0387 (6)0.0339 (6)−0.0119 (5)0.0037 (5)−0.0100 (5)
C210.0486 (8)0.0377 (7)0.0531 (9)−0.0091 (6)0.0019 (7)−0.0051 (6)
C220.0836 (13)0.0398 (8)0.0603 (10)−0.0189 (8)0.0015 (9)0.0005 (7)
C230.0819 (13)0.0590 (11)0.0600 (11)−0.0388 (10)0.0225 (10)−0.0105 (9)
C240.0466 (9)0.0712 (12)0.0680 (11)−0.0298 (8)0.0193 (8)−0.0268 (10)
C250.0360 (7)0.0533 (8)0.0483 (8)−0.0140 (6)0.0025 (6)−0.0177 (7)
C260.0306 (6)0.0418 (7)0.0335 (6)−0.0060 (5)−0.0007 (5)−0.0113 (5)
C270.0661 (12)0.0860 (15)0.0753 (13)0.0301 (11)0.0142 (10)−0.0209 (12)
O10.0515 (6)0.0415 (5)0.0361 (5)−0.0080 (4)−0.0168 (4)−0.0013 (4)
O20.0364 (5)0.0369 (5)0.0401 (5)−0.0104 (4)0.0090 (4)−0.0114 (4)
O30.0380 (5)0.0518 (6)0.0385 (5)−0.0139 (4)0.0087 (4)−0.0108 (4)
O40.0623 (7)0.0433 (6)0.0423 (6)−0.0195 (5)0.0093 (5)−0.0061 (4)
O50.0472 (6)0.0628 (7)0.0355 (5)−0.0051 (5)0.0094 (4)−0.0065 (5)
O60.0474 (6)0.0591 (7)0.0499 (6)0.0164 (5)0.0078 (5)−0.0059 (5)
Cl10.0375 (2)0.0878 (4)0.1006 (4)−0.0003 (2)−0.0181 (2)−0.0121 (3)
Geometric parameters (Å, º) top
C1—C21.371 (2)C13—O31.3753 (17)
C1—C61.3938 (19)C14—O31.3700 (18)
C1—H10.9300C14—C151.3873 (18)
C2—C31.383 (2)C14—C191.388 (2)
C2—H20.9300C15—C161.398 (2)
C3—C41.379 (2)C16—C171.376 (2)
C3—H30.9300C16—H160.9300
C4—C51.3955 (18)C17—C181.390 (3)
C4—H40.9300C17—H170.9300
C5—C61.3925 (18)C18—C191.372 (3)
C5—C91.5247 (17)C18—H180.9300
C6—O11.3634 (16)C19—H190.9300
C7—O11.4195 (17)C20—C211.384 (2)
C7—C81.5304 (17)C20—C251.3900 (19)
C7—H7A0.9700C21—C221.389 (2)
C7—H7B0.9700C21—H210.9300
C8—C261.5279 (17)C22—C231.376 (3)
C8—C91.5436 (16)C22—H220.9300
C8—C121.5497 (17)C23—C241.365 (3)
C9—C101.5203 (17)C23—H230.9300
C9—H90.9800C24—C251.387 (2)
C10—C111.3530 (18)C24—H240.9300
C10—C131.4545 (16)C25—Cl11.7404 (18)
C11—O21.3499 (14)C26—O51.1959 (16)
C11—C151.4455 (18)C26—O61.3180 (18)
C12—O21.4449 (15)C27—O61.449 (2)
C12—C201.5067 (17)C27—H27A0.9600
C12—H120.9800C27—H27B0.9600
C13—O41.2021 (18)C27—H27C0.9600
C2—C1—C6120.12 (14)O3—C13—C10118.33 (12)
C2—C1—H1119.9O3—C14—C15120.97 (12)
C6—C1—H1119.9O3—C14—C19117.76 (13)
C1—C2—C3119.92 (14)C15—C14—C19121.24 (14)
C1—C2—H2120.0C14—C15—C16118.92 (13)
C3—C2—H2120.0C14—C15—C11117.02 (12)
C4—C3—C2119.88 (14)C16—C15—C11124.05 (12)
C4—C3—H3120.1C17—C16—C15120.10 (14)
C2—C3—H3120.1C17—C16—H16120.0
C3—C4—C5121.53 (14)C15—C16—H16120.0
C3—C4—H4119.2C16—C17—C18119.80 (16)
C5—C4—H4119.2C16—C17—H17120.1
C6—C5—C4117.51 (12)C18—C17—H17120.1
C6—C5—C9120.32 (11)C19—C18—C17121.11 (15)
C4—C5—C9121.74 (12)C19—C18—H18119.4
O1—C6—C5123.90 (12)C17—C18—H18119.4
O1—C6—C1115.05 (12)C18—C19—C14118.78 (15)
C5—C6—C1120.98 (12)C18—C19—H19120.6
O1—C7—C8112.52 (11)C14—C19—H19120.6
O1—C7—H7A109.1C21—C20—C25117.39 (13)
C8—C7—H7A109.1C21—C20—C12120.77 (12)
O1—C7—H7B109.1C25—C20—C12121.82 (13)
C8—C7—H7B109.1C20—C21—C22121.45 (16)
H7A—C7—H7B107.8C20—C21—H21119.3
C26—C8—C7108.02 (10)C22—C21—H21119.3
C26—C8—C9112.31 (10)C23—C22—C21119.55 (19)
C7—C8—C9108.42 (10)C23—C22—H22120.2
C26—C8—C12108.12 (10)C21—C22—H22120.2
C7—C8—C12111.28 (10)C24—C23—C22120.32 (15)
C9—C8—C12108.71 (9)C24—C23—H23119.8
C10—C9—C5116.45 (10)C22—C23—H23119.8
C10—C9—C8108.37 (10)C23—C24—C25119.77 (17)
C5—C9—C8107.63 (9)C23—C24—H24120.1
C10—C9—H9108.0C25—C24—H24120.1
C5—C9—H9108.0C24—C25—C20121.43 (17)
C8—C9—H9108.0C24—C25—Cl1117.87 (14)
C11—C10—C13117.87 (11)C20—C25—Cl1120.70 (11)
C11—C10—C9122.10 (10)O5—C26—O6123.95 (13)
C13—C10—C9119.78 (11)O5—C26—C8123.17 (13)
O2—C11—C10124.46 (11)O6—C26—C8112.87 (11)
O2—C11—C15113.05 (11)O6—C27—H27A109.5
C10—C11—C15122.47 (11)O6—C27—H27B109.5
O2—C12—C20106.06 (10)H27A—C27—H27B109.5
O2—C12—C8109.13 (10)O6—C27—H27C109.5
C20—C12—C8115.06 (10)H27A—C27—H27C109.5
O2—C12—H12108.8H27B—C27—H27C109.5
C20—C12—H12108.8C6—O1—C7117.78 (10)
C8—C12—H12108.8C11—O2—C12116.06 (10)
O4—C13—O3115.96 (11)C14—O3—C13122.10 (10)
O4—C13—C10125.69 (13)C26—O6—C27115.38 (14)
C6—C1—C2—C30.8 (2)O2—C11—C15—C14−177.14 (12)
C1—C2—C3—C41.3 (2)C10—C11—C15—C141.25 (19)
C2—C3—C4—C5−3.0 (2)O2—C11—C15—C162.06 (19)
C3—C4—C5—C62.3 (2)C10—C11—C15—C16−179.55 (13)
C3—C4—C5—C9174.80 (14)C14—C15—C16—C170.1 (2)
C4—C5—C6—O1176.77 (12)C11—C15—C16—C17−179.04 (14)
C9—C5—C6—O14.20 (19)C15—C16—C17—C181.4 (3)
C4—C5—C6—C1−0.15 (19)C16—C17—C18—C19−1.1 (3)
C9—C5—C6—C1−172.71 (12)C17—C18—C19—C14−0.9 (3)
C2—C1—C6—O1−178.59 (13)O3—C14—C19—C18−175.40 (15)
C2—C1—C6—C5−1.4 (2)C15—C14—C19—C182.5 (2)
O1—C7—C8—C26−60.63 (13)O2—C12—C20—C2140.09 (17)
O1—C7—C8—C961.33 (13)C8—C12—C20—C21−80.64 (16)
O1—C7—C8—C12−179.17 (10)O2—C12—C20—C25−141.37 (13)
C6—C5—C9—C10−98.76 (13)C8—C12—C20—C2597.89 (15)
C4—C5—C9—C1089.00 (15)C25—C20—C21—C22−3.0 (2)
C6—C5—C9—C823.08 (16)C12—C20—C21—C22175.57 (16)
C4—C5—C9—C8−149.17 (12)C20—C21—C22—C231.0 (3)
C26—C8—C9—C10−166.73 (10)C21—C22—C23—C241.1 (3)
C7—C8—C9—C1073.98 (12)C22—C23—C24—C25−1.0 (3)
C12—C8—C9—C10−47.12 (12)C23—C24—C25—C20−1.1 (3)
C26—C8—C9—C566.55 (13)C23—C24—C25—Cl1179.17 (15)
C7—C8—C9—C5−52.74 (13)C21—C20—C25—C243.1 (2)
C12—C8—C9—C5−173.85 (10)C12—C20—C25—C24−175.47 (15)
C5—C9—C10—C11138.72 (12)C21—C20—C25—Cl1−177.20 (12)
C8—C9—C10—C1117.27 (16)C12—C20—C25—Cl14.2 (2)
C5—C9—C10—C13−47.09 (15)C7—C8—C26—O5−32.65 (17)
C8—C9—C10—C13−168.54 (11)C9—C8—C26—O5−152.17 (13)
C13—C10—C11—O2−174.11 (12)C12—C8—C26—O587.89 (15)
C9—C10—C11—O20.2 (2)C7—C8—C26—O6148.50 (12)
C13—C10—C11—C157.69 (19)C9—C8—C26—O628.98 (15)
C9—C10—C11—C15−178.02 (11)C12—C8—C26—O6−90.96 (13)
C26—C8—C12—O2−173.94 (10)C5—C6—O1—C71.24 (19)
C7—C8—C12—O2−55.46 (13)C1—C6—O1—C7178.32 (12)
C9—C8—C12—O263.88 (13)C8—C7—O1—C6−34.54 (16)
C26—C8—C12—C20−54.89 (14)C10—C11—O2—C1215.68 (18)
C7—C8—C12—C2063.59 (14)C15—C11—O2—C12−165.96 (11)
C9—C8—C12—C20−177.08 (10)C20—C12—O2—C11−171.76 (10)
C11—C10—C13—O4165.57 (14)C8—C12—O2—C11−47.26 (14)
C9—C10—C13—O4−8.9 (2)C15—C14—O3—C13−0.6 (2)
C11—C10—C13—O3−13.09 (18)C19—C14—O3—C13177.27 (13)
C9—C10—C13—O3172.48 (11)O4—C13—O3—C14−168.99 (13)
O3—C14—C15—C16175.70 (13)C10—C13—O3—C149.80 (19)
C19—C14—C15—C16−2.1 (2)O5—C26—O6—C27−1.6 (2)
O3—C14—C15—C11−5.06 (19)C8—C26—O6—C27177.28 (16)
C19—C14—C15—C11177.12 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O5i0.932.593.271 (2)130
C12—H12···O4ii0.982.533.3316 (16)139
C23—H23···O5iii0.932.473.355 (3)159
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formulaC27H19ClO6
Mr474.87
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.4441 (3), 9.7556 (3), 13.8546 (5)
α, β, γ (°)73.831 (2), 82.858 (2), 87.962 (2)
V (Å3)1087.65 (6)
Z2
Radiation typeMo Kα
µ (mm−1)0.22
Crystal size (mm)0.30 × 0.25 × 0.25
Data collection
DiffractometerBruker Kappa APEXII CCD
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		26685, 6336, 4968
Rint0.026
(sin θ/λ)max (Å−1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.143, 1.01
No. of reflections6336
No. of parameters308
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.57, −0.52

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O5i0.932.593.271 (2)130
C12—H12···O4ii0.982.533.3316 (16)139
C23—H23···O5iii0.932.473.355 (3)159
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) −x, −y, −z+1.
 

Acknowledgements

K. Swaminathan and K. Sethusankar thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray intensity data collection and Dr V. Murugan, Head of the Department of Physics, RKM Vivekananda College, Chennai, India, for providing facilities in the department to carry out this work.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
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 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
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ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2673
https://doi.org/10.1107/S1600536811037196
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