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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(E)-9-(4-Chloro­styr­yl)-3,4,5,6,7,9-hexa­hydro-2H-xanthene-1,8-dione

aCenter for Neuro-Medicine, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, and bAdvanced Analysis Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea
*Correspondence e-mail: j9601@kist.re.kr

(Received 4 January 2012; accepted 18 January 2012; online 21 January 2012)

In the title compound, C21H19ClO3, the two cyclo­hexenone rings adopt half-chair conformations, whereas the pyran ring adopts a boat conformation. The 4-chloro­phenyl ring is almost perpendicular to the plane through the four C atoms of the pyran ring [dihedral angle = 87.97 (6)°]. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into a chain parallel to the a-axis.

Related literature

For the biological activity of xanthenes and their derivatives, see: Lee et al. (2011[Lee, J. K., Min, S.-J., Cho, Y. S., Cha, J. H. & Sato, H. (2011). Acta Cryst. E67, o3407.]). For related structures of xanthenes, see: Asad et al. (2012[Asad, M., Oo, C.-W., Osman, H., Fun, H.-K. & Arshad, S. (2012). Acta Cryst. E68, o38.]); Fun et al. (2011[Fun, H.-K., Loh, W.-S., Rajesh, K., Vijayakumar, V. & Sarveswari, S. (2011). Acta Cryst. E67, o1876-o1877.]); Mehdi et al. (2011[Mehdi, S. H., Sulaiman, O., Ghalib, R. M., Yeap, C. S. & Fun, H.-K. (2011). Acta Cryst. E67, o1719-o1720.]).

[Scheme 1]

Experimental

Crystal data
  • C21H19ClO3

  • Mr = 354.83

  • Monoclinic, P 21 /n

  • a = 5.6262 (7) Å

  • b = 16.273 (2) Å

  • c = 18.570 (3) Å

  • β = 90.125 (4)°

  • V = 1700.2 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 296 K

  • 0.30 × 0.02 × 0.02 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Rigaku, 1995[Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.490, Tmax = 0.995

  • 13165 measured reflections

  • 3066 independent reflections

  • 1304 reflections with F2 > 2σ(F2)

  • Rint = 0.130

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.157

  • S = 0.95

  • 3066 reflections

  • 234 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C18—H18A⋯O3i 0.97 2.50 3.316 (6) 142
Symmetry code: (i) x-1, y, z.

Data collection: RAPID-AUTO (Rigaku, 2006[Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: IL MILIONE (Burla et al., 2007[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: CrystalStructure.

Supporting information


Comment top

As part of our ongoing study of the substituent effect on the solide state structures of xanthene derivatives (Lee et al., 2011) the crystal structure of the title compound (I) (Fig. 1)is presented.

The bond lengths and angles are normal and correspond to those observed in related structures (Asad et al., 2012; Fun et al., 2011; Mehdi et al., 2011). In the title compound, the dihedral angle between the 4-chlorophenyl and xanthenedione is 87.97 (6)°. Two cyclohexenone rings display a half-chair conformation whereas the pyran ring adopts a boat conformation. In the crystal packing (Fig. 2), intermolecular C18—H18A···O3 hydrogen bond (Table 1) link molecules into a chain.

Related literature top

For the biological activity of xanthenes and their derivatives, see: Lee et al. (2011). For related structures of xanthenes, see: Asad et al. (2012); Fun et al. (2011); Mehdi et al. (2011).

Experimental top

To solution of (E))-2,2'-(3-(4-chlorophenyl)prop-2-ene-1,1-diyl)bis (3-hydroxycyclohex-2-enone) (1.25 mmol) methanol (12.5 ml) and catalytic amounts of sulfuric acid (0.2 ml) in under nitrogen atmosphere were added. After stirring for 3 h, the solvent was evaporated and the remaining residue was dissolved in ethyl acetate. The mixture was neutralized with saturated sodium bicarbonate and the solution was extracted with ethyl acetate. The resulting solid was purified by recrystallization from ethanol and methylene chloride to afford white needle crystals suitable for X-ray analysis.

Refinement top

All hydrogen atoms were positioned geometrically and refined using a riding model with C—H = 0.93–1.06 Å and Uiso(H) = 1.2 or 1.5Ueq(C).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: IL MILIONE (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atomic numbering and 50% probability displacement ellipsoid.
[Figure 2] Fig. 2. The crystal packing of the title compound with intermolecular contacts (dashed lines). The H atoms not involved in the intermolecular interactions have been omitted for clarity.
(E)-9-(4-Chlorostyryl)-3,4,5,6,7,9-hexahydro-2H-xanthene- 1,8-dione top
Crystal data top
C21H19ClO3F(000) = 744.00
Mr = 354.83Dx = 1.386 Mg m3
Monoclinic, P21/nMelting point: 474 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71075 Å
a = 5.6262 (7) ÅCell parameters from 6227 reflections
b = 16.273 (2) Åθ = 3.3–25.3°
c = 18.570 (3) ŵ = 0.24 mm1
β = 90.125 (4)°T = 296 K
V = 1700.2 (4) Å3Needle, yellow
Z = 40.30 × 0.02 × 0.02 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1304 reflections with F2 > 2σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.130
ω scansθmax = 25.3°
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
h = 66
Tmin = 0.490, Tmax = 0.995k = 1919
13165 measured reflectionsl = 2222
3066 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 0.95 w = 1/[σ2(Fo2) + (0.0638P)2]
where P = (Fo2 + 2Fc2)/3
3066 reflections(Δ/σ)max < 0.001
234 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.24 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C21H19ClO3V = 1700.2 (4) Å3
Mr = 354.83Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.6262 (7) ŵ = 0.24 mm1
b = 16.273 (2) ÅT = 296 K
c = 18.570 (3) Å0.30 × 0.02 × 0.02 mm
β = 90.125 (4)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3066 independent reflections
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
1304 reflections with F2 > 2σ(F2)
Tmin = 0.490, Tmax = 0.995Rint = 0.130
13165 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 0.95Δρmax = 0.30 e Å3
3066 reflectionsΔρmin = 0.24 e Å3
234 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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.2944 (3)0.68648 (7)0.50318 (7)0.0742 (5)
O10.6470 (5)0.24438 (17)0.19262 (15)0.0546 (8)
O21.2810 (6)0.43358 (19)0.17692 (16)0.0658 (9)
O31.1501 (6)0.23843 (19)0.39585 (17)0.0703 (10)
C10.6501 (8)0.5040 (3)0.3556 (3)0.0485 (11)
C20.4387 (8)0.5424 (3)0.3366 (3)0.0590 (12)
C30.3346 (8)0.6004 (3)0.3809 (3)0.0597 (12)
C40.4386 (8)0.6189 (3)0.4455 (3)0.0517 (11)
C50.6509 (8)0.5839 (3)0.4652 (3)0.0585 (12)
C60.7543 (8)0.5266 (3)0.4206 (3)0.0556 (12)
C70.7497 (8)0.4404 (3)0.3081 (3)0.0523 (12)
C80.9399 (9)0.3960 (3)0.3186 (3)0.0514 (11)
C91.0229 (7)0.3270 (3)0.2694 (2)0.0479 (11)
C100.9648 (7)0.3411 (3)0.1915 (2)0.0450 (11)
C111.1125 (8)0.3975 (3)0.1491 (3)0.0501 (11)
C121.0565 (8)0.4065 (3)0.0708 (2)0.0566 (12)
C130.7925 (8)0.3968 (3)0.0548 (3)0.0596 (13)
C140.7031 (7)0.3152 (3)0.0832 (2)0.0517 (11)
C150.7850 (7)0.3023 (3)0.1583 (3)0.0457 (11)
C160.7265 (8)0.2140 (3)0.2576 (3)0.0515 (12)
C170.5817 (8)0.1420 (3)0.2807 (3)0.0604 (13)
C180.6238 (9)0.1242 (3)0.3605 (3)0.0788 (16)
C190.8789 (9)0.1274 (3)0.3801 (3)0.0731 (15)
C200.9904 (8)0.2077 (3)0.3599 (3)0.0552 (12)
C210.9076 (7)0.2473 (3)0.2938 (3)0.0475 (11)
H20.36570.52890.29320.0707*
H30.19500.62660.36690.0716*
H50.72420.59870.50820.0702*
H60.89720.50240.43430.0667*
H91.19560.32150.27430.0575*
H12A1.14450.36550.04390.0679*
H12B1.10830.46020.05460.0679*
H13A0.70490.44130.07730.0715*
H13B0.76600.39970.00330.0715*
H14A0.53080.31430.08160.0620*
H14B0.76140.27100.05300.0620*
H17A0.62510.09420.25230.0725*
H17B0.41460.15330.27250.0725*
H18A0.53750.16400.38910.0946*
H18B0.56170.07010.37190.0946*
H19A0.96220.08310.35600.0877*
H19B0.89540.11910.43170.0877*
H81.046 (9)0.408 (3)0.364 (3)0.12 (2)*
H70.655 (7)0.435 (3)0.266 (3)0.061 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0885 (10)0.0694 (8)0.0646 (9)0.0114 (7)0.0153 (7)0.0112 (7)
O10.0528 (17)0.0641 (18)0.047 (2)0.0088 (15)0.0037 (15)0.0049 (16)
O20.062 (2)0.084 (3)0.052 (2)0.0199 (17)0.0020 (16)0.0004 (17)
O30.069 (3)0.089 (3)0.053 (3)0.0059 (18)0.0130 (17)0.0064 (18)
C10.055 (3)0.056 (3)0.035 (3)0.009 (3)0.005 (2)0.000 (2)
C20.053 (3)0.076 (3)0.048 (3)0.007 (3)0.006 (3)0.008 (3)
C30.052 (3)0.069 (3)0.057 (4)0.009 (3)0.001 (3)0.001 (3)
C40.062 (3)0.051 (3)0.042 (3)0.004 (3)0.012 (3)0.004 (3)
C50.063 (3)0.065 (3)0.048 (3)0.002 (3)0.008 (3)0.008 (3)
C60.057 (3)0.060 (3)0.050 (4)0.011 (3)0.001 (3)0.003 (3)
C70.050 (3)0.069 (3)0.038 (3)0.007 (3)0.005 (3)0.011 (3)
C80.054 (3)0.057 (3)0.043 (3)0.005 (3)0.001 (3)0.005 (3)
C90.048 (3)0.062 (3)0.033 (3)0.002 (2)0.0016 (19)0.005 (3)
C100.051 (3)0.050 (3)0.034 (3)0.008 (2)0.000 (2)0.000 (2)
C110.053 (3)0.057 (3)0.040 (3)0.007 (3)0.007 (3)0.002 (3)
C120.066 (3)0.066 (3)0.038 (3)0.000 (3)0.002 (3)0.004 (3)
C130.070 (4)0.071 (3)0.038 (3)0.005 (3)0.006 (3)0.003 (3)
C140.052 (3)0.062 (3)0.041 (3)0.003 (3)0.001 (2)0.006 (3)
C150.048 (3)0.053 (3)0.036 (3)0.004 (3)0.003 (2)0.004 (2)
C160.061 (3)0.056 (3)0.038 (3)0.011 (3)0.003 (3)0.009 (3)
C170.063 (3)0.059 (3)0.060 (4)0.007 (3)0.008 (3)0.002 (3)
C180.084 (4)0.076 (4)0.076 (4)0.001 (3)0.010 (3)0.025 (3)
C190.083 (4)0.073 (4)0.062 (4)0.011 (3)0.005 (3)0.020 (3)
C200.062 (3)0.063 (3)0.041 (3)0.014 (3)0.007 (3)0.001 (3)
C210.052 (3)0.053 (3)0.037 (3)0.010 (3)0.001 (2)0.002 (3)
Geometric parameters (Å, º) top
Cl1—C41.737 (5)C17—C181.529 (7)
O1—C151.377 (5)C18—C191.481 (7)
O1—C161.379 (6)C19—C201.499 (7)
O2—C111.228 (6)C20—C211.461 (6)
O3—C201.225 (6)C2—H20.930
C1—C21.388 (6)C3—H30.930
C1—C61.391 (6)C5—H50.930
C1—C71.472 (6)C6—H60.930
C2—C31.383 (7)C7—H70.96 (4)
C3—C41.368 (7)C8—H81.06 (6)
C4—C51.372 (7)C9—H90.980
C5—C61.376 (6)C12—H12A0.970
C7—C81.306 (7)C12—H12B0.970
C8—C91.520 (6)C13—H13A0.970
C9—C101.501 (6)C13—H13B0.970
C9—C211.520 (6)C14—H14A0.970
C10—C111.468 (6)C14—H14B0.970
C10—C151.341 (6)C17—H17A0.970
C11—C121.495 (6)C17—H17B0.970
C12—C131.522 (6)C18—H18A0.970
C13—C141.515 (6)C18—H18B0.970
C14—C151.483 (6)C19—H19A0.970
C16—C171.491 (6)C19—H19B0.970
C16—C211.335 (6)
O1···C92.881 (5)C11···H18Bvi3.0007
O2···C83.317 (6)C12···H12Bxi3.3132
O2···C92.842 (5)C12···H13Bxi3.5843
O2···C153.531 (5)C12···H14Aii3.0675
O3···C83.165 (6)C12···H18Axii3.5651
O3···C92.845 (5)C12···H18Bvi2.9442
O3···C163.521 (6)C12···H19Bxii3.2416
O3···C183.556 (6)C13···H12Bxi3.1400
C1···C42.777 (6)C13···H18Axii3.5169
C2···C52.752 (7)C13···H18Bvi3.2365
C3···C62.749 (6)C13···H19Bv3.2044
C6···C83.034 (6)C14···H12Aiv3.3275
C7···C102.962 (6)C14···H19Bv3.4699
C7···C153.581 (7)C16···H9iv3.4764
C7···C213.275 (6)C17···H2viii3.4042
C8···C113.296 (7)C17···H3viii3.1582
C8···C153.455 (6)C18···H12Axiii3.4111
C8···C163.389 (6)C18···H12Bxiv3.3639
C8···C203.170 (6)C18···H13Axiv3.3343
C10···C132.862 (6)C18···H13Bxiii3.3548
C10···C162.756 (6)C19···H12Axiii3.3187
C11···C142.930 (6)C19···H13Axiv3.1656
C12···C152.804 (6)C19···H13Biii3.1845
C15···C212.757 (6)C20···H13Biii3.5396
C16···C192.809 (7)C20···H17Bii3.0220
C17···C202.929 (7)C20···H18Aii3.2042
C18···C212.847 (7)C21···H17Bii3.2623
Cl1···O3i3.359 (4)H2···O2iv2.7005
Cl1···C20i3.467 (5)H2···C8iv3.2630
O2···C2ii3.565 (6)H2···C17vii3.4042
O2···C7ii3.588 (6)H2···H9iv3.5252
O2···C14ii3.521 (5)H2···H17Avii3.0753
O2···C15ii3.568 (5)H2···H17Avi3.1724
O3···Cl1i3.359 (4)H2···H17Bvii2.8393
O3···C14iii3.599 (5)H2···H19Avi3.0672
O3···C18ii3.317 (6)H2···H8iv2.9741
C2···O2iv3.565 (6)H3···O1vii2.9310
C3···C6iv3.557 (6)H3···C6iv3.1309
C5···C5i3.466 (6)H3···C17vii3.1582
C5···C6i3.598 (6)H3···H6iv2.9096
C6···C3ii3.557 (6)H3···H14Avii3.4449
C6···C5i3.598 (6)H3···H17Avii2.8986
C7···O2iv3.588 (6)H3···H17Bvii2.6940
C14···O2iv3.521 (5)H5···Cl1ii3.5138
C14···O3v3.599 (5)H5···O3x3.2704
C15···O2iv3.568 (5)H5···H6x2.8933
C18···O3iv3.317 (6)H5···H14Bvi3.0276
C20···Cl1i3.467 (5)H5···H8x2.6944
Cl1···H32.7686H6···Cl1i3.4592
Cl1···H52.8101H6···C3ii3.0969
O1···H14A2.4421H6···C4ii3.5932
O1···H14B2.7084H6···C4i3.5306
O1···H17A2.6866H6···C5x3.4489
O1···H17B2.4731H6···C6x3.3615
O1···H73.38 (4)H6···H3ii2.9096
O2···H92.6141H6···H5x2.8933
O2···H12A2.8131H6···H6x2.6985
O2···H12B2.5062H9···O1ii3.2165
O3···H92.6434H9···C16ii3.4764
O3···H19A2.8377H9···H2ii3.5252
O3···H19B2.5037H9···H17Bii3.0027
O3···H82.88 (5)H9···H7ii3.1772
C1···H33.2526H12A···Cl1xiv3.0610
C1···H53.2525H12A···C14ii3.3275
C1···H82.72 (5)H12A···C18xii3.4111
C2···H63.2173H12A···C19xii3.3187
C2···H72.51 (4)H12A···H13Aii3.4409
C3···H53.2211H12A···H14Aii2.4297
C4···H23.2107H12A···H18Axii2.9741
C4···H63.2087H12A···H18Bxii3.3927
C5···H33.2214H12A···H19Bxii2.5322
C6···H23.2183H12B···C12xi3.3132
C6···H82.74 (5)H12B···C13xi3.1400
C6···H73.29 (4)H12B···C18vi3.3639
C7···H22.6112H12B···H12Bxi2.6951
C7···H62.6827H12B···H13Aii3.3961
C7···H93.2300H12B···H13Axi3.1116
C8···H62.7711H12B···H13Bxi2.6186
C9···H72.71 (4)H12B···H14Aii3.3965
C10···H12A2.9504H12B···H18Avi3.5734
C10···H12B3.2984H12B···H18Bvi2.4456
C10···H13A3.0459H12B···H18Bxii3.4387
C10···H14A3.2078H12B···H19Aix3.5456
C10···H14B3.0353H12B···H19Bxii3.0834
C10···H83.42 (6)H13A···O2iv3.0247
C10···H72.70 (4)H13A···C18vi3.3343
C11···H92.6738H13A···C19vi3.1656
C11···H13A2.7447H13A···H12Aiv3.4409
C11···H13B3.3340H13A···H12Biv3.3961
C11···H14B3.3630H13A···H12Bxi3.1116
C11···H73.42 (4)H13A···H18Bvi2.6469
C12···H14A3.3231H13A···H19Avi2.7840
C12···H14B2.7793H13A···H19Bvi2.9537
C14···H12A2.7165H13A···H19Bv3.3601
C14···H12B3.3254H13B···O3v3.0736
C15···H93.1710H13B···C12xi3.5843
C15···H12A3.1122H13B···C18xii3.3548
C15···H13A2.7537H13B···C19v3.1845
C15···H13B3.2884H13B···C20v3.5396
C15···H73.03 (4)H13B···H12Bxi2.6186
C16···H93.1811H13B···H18Axii2.8134
C16···H18A2.7863H13B···H18Bxii2.9969
C16···H18B3.2940H13B···H19Av3.2336
C16···H19A3.1021H13B···H19Bv2.4891
C17···H19A2.7286H14A···Cl1viii3.1848
C17···H19B3.3306H14A···O2iv2.9806
C19···H17A2.8197H14A···C11iv2.9919
C19···H17B3.3132H14A···C12iv3.0675
C20···H92.7008H14A···H3viii3.4449
C20···H17A3.4068H14A···H12Aiv2.4297
C20···H18A2.7016H14A···H12Biv3.3965
C20···H18B3.2989H14A···H19Bv3.0826
C20···H83.28 (5)H14B···Cl1viii3.5700
C21···H17A3.0540H14B···Cl1xiv3.0390
C21···H17B3.1924H14B···O3v2.9866
C21···H18A3.0528H14B···C4xiv2.9960
C21···H19A2.9276H14B···C5xiv3.1038
C21···H19B3.3026H14B···H5xiv3.0276
C21···H83.03 (5)H14B···H18Axii3.5788
C21···H73.40 (4)H14B···H19Bv3.5342
H2···H32.3074H17A···C1xiv2.7895
H2···H72.2949H17A···C2xiv3.0787
H5···H62.3001H17A···C3viii3.5763
H6···H82.1765H17A···C6xiv3.4635
H6···H73.5875H17A···C7xiv2.8328
H9···H82.3468H17A···C8xiv3.5036
H9···H73.5592H17A···H2viii3.0753
H12A···H13A2.8331H17A···H2xiv3.1724
H12A···H13B2.3250H17A···H3viii2.8986
H12A···H14B2.6532H17A···H7xiv2.8962
H12B···H13A2.3297H17B···O3iv3.0658
H12B···H13B2.3630H17B···C2viii3.3599
H13A···H14A2.2882H17B···C3viii3.2863
H13A···H14B2.8251H17B···C9iv3.5857
H13A···H73.5115H17B···C20iv3.0220
H13B···H14A2.4098H17B···C21iv3.2623
H13B···H14B2.2880H17B···H2viii2.8393
H17A···H18A2.8272H17B···H3viii2.6940
H17A···H18B2.2832H17B···H9iv3.0027
H17A···H19A2.7061H17B···H19Aiv3.1948
H17B···H18A2.2790H18A···Cl1i3.2869
H17B···H18B2.4325H18A···O3iv2.4963
H18A···H19A2.7983H18A···C12xiii3.5651
H18A···H19B2.2821H18A···C13xiii3.5169
H18B···H19A2.2829H18A···C20iv3.2042
H18B···H19B2.3207H18A···H12Axiii2.9741
H8···H72.89 (7)H18A···H12Bxiv3.5734
Cl1···H5iv3.5138H18A···H13Bxiii2.8134
Cl1···H6i3.4592H18A···H14Bxiii3.5788
Cl1···H12Avi3.0610H18A···H19Aiv3.5469
Cl1···H14Avii3.1848H18B···O2xiv3.0768
Cl1···H14Bvii3.5700H18B···C11xiv3.0007
Cl1···H14Bvi3.0390H18B···C12xiv2.9442
Cl1···H18Ai3.2869H18B···C13xiv3.2365
Cl1···H19Bi3.5522H18B···H12Axiii3.3927
Cl1···H8i3.48 (6)H18B···H12Bxiv2.4456
O1···H3viii2.9310H18B···H12Bxiii3.4387
O1···H9iv3.2165H18B···H13Axiv2.6469
O2···H2ii2.7005H18B···H13Bxiii2.9969
O2···H13Aii3.0247H18B···H19Aiv3.3917
O2···H14Aii2.9806H19A···O2xv2.8956
O2···H18Bvi3.0768H19A···H2xiv3.0672
O2···H19Aix2.8956H19A···H12Bxv3.5456
O2···H7ii2.67 (4)H19A···H13Axiv2.7840
O3···H5x3.2704H19A···H13Biii3.2336
O3···H13Biii3.0736H19A···H17Bii3.1948
O3···H14Biii2.9866H19A···H18Aii3.5469
O3···H17Bii3.0658H19A···H18Bii3.3917
O3···H18Aii2.4963H19A···H7xiv3.3714
C1···H17Avi2.7895H19B···Cl1i3.5522
C2···H17Avi3.0787H19B···C12xiii3.2416
C2···H17Bvii3.3599H19B···C13iii3.2044
C2···H8iv3.15 (5)H19B···C14iii3.4699
C3···H6iv3.0969H19B···H12Axiii2.5322
C3···H17Avii3.5763H19B···H12Bxiii3.0834
C3···H17Bvii3.2863H19B···H13Axiv2.9537
C3···H8iv3.54 (5)H19B···H13Aiii3.3601
C4···H6iv3.5932H19B···H13Biii2.4891
C4···H6i3.5306H19B···H14Aiii3.0826
C4···H14Bvi2.9960H19B···H14Biii3.5342
C5···H6x3.4489H8···Cl1i3.48 (6)
C5···H14Bvi3.1038H8···C2ii3.15 (5)
C5···H8x3.59 (6)H8···C3ii3.54 (5)
C6···H3ii3.1309H8···C5x3.59 (6)
C6···H6x3.3615H8···H2ii2.9741
C6···H17Avi3.4635H8···H5x2.6944
C7···H17Avi2.8328H7···O2iv2.67 (4)
C8···H2ii3.2630H7···H9iv3.1772
C8···H17Avi3.5036H7···H17Avi2.8962
C9···H17Bii3.5857H7···H19Avi3.3714
C11···H14Aii2.9919
C15—O1—C16117.9 (3)C4—C3—H3120.295
C2—C1—C6117.4 (4)C4—C5—H5120.343
C2—C1—C7119.5 (4)C6—C5—H5120.335
C6—C1—C7123.1 (4)C1—C6—H6119.226
C1—C2—C3121.3 (4)C5—C6—H6119.214
C2—C3—C4119.4 (4)C1—C7—H7110 (3)
Cl1—C4—C3118.7 (4)C8—C7—H7122 (3)
Cl1—C4—C5120.4 (4)C7—C8—H8118 (3)
C3—C4—C5120.9 (4)C9—C8—H8117 (3)
C4—C5—C6119.3 (4)C8—C9—H9108.517
C1—C6—C5121.6 (4)C10—C9—H9108.517
C1—C7—C8127.8 (5)C21—C9—H9108.517
C7—C8—C9124.8 (4)C11—C12—H12A109.090
C8—C9—C10113.6 (4)C11—C12—H12B109.095
C8—C9—C21108.6 (4)C13—C12—H12A109.096
C10—C9—C21109.0 (4)C13—C12—H12B109.096
C9—C10—C11119.3 (4)H12A—C12—H12B107.839
C9—C10—C15122.2 (4)C12—C13—H13A109.587
C11—C10—C15118.4 (4)C12—C13—H13B109.587
O2—C11—C10120.7 (4)C14—C13—H13A109.580
O2—C11—C12121.5 (4)C14—C13—H13B109.577
C10—C11—C12117.7 (4)H13A—C13—H13B108.127
C11—C12—C13112.5 (4)C13—C14—H14A109.571
C12—C13—C14110.3 (4)C13—C14—H14B109.570
C13—C14—C15110.4 (4)C15—C14—H14A109.565
O1—C15—C10122.4 (4)C15—C14—H14B109.565
O1—C15—C14111.0 (4)H14A—C14—H14B108.112
C10—C15—C14126.7 (4)C16—C17—H17A109.647
O1—C16—C17110.9 (4)C16—C17—H17B109.641
O1—C16—C21122.8 (4)C18—C17—H17A109.632
C17—C16—C21126.3 (4)C18—C17—H17B109.638
C16—C17—C18110.1 (4)H17A—C17—H17B108.161
C17—C18—C19112.4 (5)C17—C18—H18A109.137
C18—C19—C20112.0 (4)C17—C18—H18B109.133
O3—C20—C19121.7 (4)C19—C18—H18A109.133
O3—C20—C21120.6 (4)C19—C18—H18B109.127
C19—C20—C21117.6 (4)H18A—C18—H18B107.854
C9—C21—C16121.5 (4)C18—C19—H19A109.215
C9—C21—C20119.5 (4)C18—C19—H19B109.211
C16—C21—C20119.0 (4)C20—C19—H19A109.213
C1—C2—H2119.337C20—C19—H19B109.201
C3—C2—H2119.331H19A—C19—H19B107.906
C2—C3—H3120.285
C15—O1—C16—C17169.7 (3)C9—C10—C11—C12176.9 (3)
C15—O1—C16—C2111.3 (6)C9—C10—C15—O12.6 (6)
C16—O1—C15—C1013.3 (5)C9—C10—C15—C14176.0 (4)
C16—O1—C15—C14167.9 (3)C11—C10—C15—O1175.7 (4)
C2—C1—C6—C51.0 (6)C11—C10—C15—C145.7 (6)
C6—C1—C2—C30.6 (6)C15—C10—C11—O2179.0 (4)
C2—C1—C7—C8177.1 (4)C15—C10—C11—C121.4 (6)
C7—C1—C2—C3177.7 (4)O2—C11—C12—C13150.2 (4)
C6—C1—C7—C81.0 (7)C10—C11—C12—C1332.2 (5)
C7—C1—C6—C5177.2 (4)C11—C12—C13—C1455.7 (5)
C1—C2—C3—C41.6 (7)C12—C13—C14—C1547.7 (4)
C2—C3—C4—Cl1175.5 (4)C13—C14—C15—O1160.2 (3)
C2—C3—C4—C53.4 (7)C13—C14—C15—C1018.6 (6)
Cl1—C4—C5—C6175.9 (3)O1—C16—C17—C18164.2 (3)
C3—C4—C5—C63.0 (7)O1—C16—C21—C96.5 (6)
C4—C5—C6—C10.7 (6)O1—C16—C21—C20175.8 (3)
C1—C7—C8—C9175.5 (4)C17—C16—C21—C9172.5 (4)
C7—C8—C9—C1032.5 (6)C17—C16—C21—C205.3 (7)
C7—C8—C9—C2188.9 (5)C21—C16—C17—C1814.8 (6)
C8—C9—C10—C1178.4 (5)C16—C17—C18—C1944.7 (5)
C8—C9—C10—C15103.2 (4)C17—C18—C19—C2055.4 (5)
C8—C9—C21—C16104.4 (4)C18—C19—C20—O3146.9 (5)
C8—C9—C21—C2073.3 (5)C18—C19—C20—C2135.1 (6)
C10—C9—C21—C1619.8 (5)O3—C20—C21—C90.6 (6)
C10—C9—C21—C20162.5 (3)O3—C20—C21—C16177.2 (4)
C21—C9—C10—C11160.4 (3)C19—C20—C21—C9177.4 (4)
C21—C9—C10—C1518.0 (5)C19—C20—C21—C164.8 (6)
C9—C10—C11—O20.7 (6)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z; (iii) x+1/2, y+1/2, z+1/2; (iv) x1, y, z; (v) x1/2, y+1/2, z1/2; (vi) x+3/2, y+1/2, z+1/2; (vii) x+1/2, y+1/2, z+1/2; (viii) x+1/2, y1/2, z+1/2; (ix) x+5/2, y+1/2, z+1/2; (x) x+2, y+1, z+1; (xi) x+2, y+1, z; (xii) x+1/2, y+1/2, z1/2; (xiii) x1/2, y+1/2, z+1/2; (xiv) x+3/2, y1/2, z+1/2; (xv) x+5/2, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···O3iv0.972.503.316 (6)142
Symmetry code: (iv) x1, y, z.

Experimental details

Crystal data
Chemical formulaC21H19ClO3
Mr354.83
Crystal system, space groupMonoclinic, P21/n
Temperature (K)296
a, b, c (Å)5.6262 (7), 16.273 (2), 18.570 (3)
β (°) 90.125 (4)
V3)1700.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.30 × 0.02 × 0.02
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Rigaku, 1995)
Tmin, Tmax0.490, 0.995
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
13165, 3066, 1304
Rint0.130
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.157, 0.95
No. of reflections3066
No. of parameters234
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.30, 0.24

Computer programs: RAPID-AUTO (Rigaku, 2006), IL MILIONE (Burla et al., 2007), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010) and DIAMOND (Brandenburg, 2006), CrystalStructure (Rigaku, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···O3i0.9702.49633.316 (6)142.00
Symmetry code: (i) x1, y, z.
 

Acknowledgements

Fiancial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.

References

First citationAsad, M., Oo, C.-W., Osman, H., Fun, H.-K. & Arshad, S. (2012). Acta Cryst. E68, o38.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBurla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609–613.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationFun, H.-K., Loh, W.-S., Rajesh, K., Vijayakumar, V. & Sarveswari, S. (2011). Acta Cryst. E67, o1876–o1877.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLee, J. K., Min, S.-J., Cho, Y. S., Cha, J. H. & Sato, H. (2011). Acta Cryst. E67, o3407.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationMehdi, S. H., Sulaiman, O., Ghalib, R. M., Yeap, C. S. & Fun, H.-K. (2011). Acta Cryst. E67, o1719–o1720.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationRigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds