organic compounds
(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
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). For related structures of xanthenes, see: Asad et al. (2012); Fun et al. (2011); Mehdi et al. (2011).
Experimental
Crystal data
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Refinement
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Data collection: RAPID-AUTO (Rigaku, 2006); cell RAPID-AUTO; data reduction: RAPID-AUTO; 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.
Supporting information
10.1107/S1600536812002139/kp2380sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812002139/kp2380Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812002139/kp2380Isup3.cml
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.
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).
Data collection: RAPID-AUTO (Rigaku, 2006); cell
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).C21H19ClO3 | F(000) = 744.00 |
Mr = 354.83 | Dx = 1.386 Mg m−3 |
Monoclinic, P21/n | Melting point: 474 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71075 Å |
a = 5.6262 (7) Å | Cell parameters from 6227 reflections |
b = 16.273 (2) Å | θ = 3.3–25.3° |
c = 18.570 (3) Å | µ = 0.24 mm−1 |
β = 90.125 (4)° | T = 296 K |
V = 1700.2 (4) Å3 | Needle, yellow |
Z = 4 | 0.30 × 0.02 × 0.02 mm |
Rigaku R-AXIS RAPID diffractometer | 1304 reflections with F2 > 2σ(F2) |
Detector resolution: 10.000 pixels mm-1 | Rint = 0.130 |
ω scans | θmax = 25.3° |
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995) | h = −6→6 |
Tmin = 0.490, Tmax = 0.995 | k = −19→19 |
13165 measured reflections | l = −22→22 |
3066 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H 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 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Primary atom site location: structure-invariant direct methods |
C21H19ClO3 | V = 1700.2 (4) Å3 |
Mr = 354.83 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 5.6262 (7) Å | µ = 0.24 mm−1 |
b = 16.273 (2) Å | T = 296 K |
c = 18.570 (3) Å | 0.30 × 0.02 × 0.02 mm |
β = 90.125 (4)° |
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 = 0.995 | Rint = 0.130 |
13165 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.157 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | Δρmax = 0.30 e Å−3 |
3066 reflections | Δρmin = −0.24 e Å−3 |
234 parameters |
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). |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.2944 (3) | 0.68648 (7) | 0.50318 (7) | 0.0742 (5) | |
O1 | 0.6470 (5) | 0.24438 (17) | 0.19262 (15) | 0.0546 (8) | |
O2 | 1.2810 (6) | 0.43358 (19) | 0.17692 (16) | 0.0658 (9) | |
O3 | 1.1501 (6) | 0.23843 (19) | 0.39585 (17) | 0.0703 (10) | |
C1 | 0.6501 (8) | 0.5040 (3) | 0.3556 (3) | 0.0485 (11) | |
C2 | 0.4387 (8) | 0.5424 (3) | 0.3366 (3) | 0.0590 (12) | |
C3 | 0.3346 (8) | 0.6004 (3) | 0.3809 (3) | 0.0597 (12) | |
C4 | 0.4386 (8) | 0.6189 (3) | 0.4455 (3) | 0.0517 (11) | |
C5 | 0.6509 (8) | 0.5839 (3) | 0.4652 (3) | 0.0585 (12) | |
C6 | 0.7543 (8) | 0.5266 (3) | 0.4206 (3) | 0.0556 (12) | |
C7 | 0.7497 (8) | 0.4404 (3) | 0.3081 (3) | 0.0523 (12) | |
C8 | 0.9399 (9) | 0.3960 (3) | 0.3186 (3) | 0.0514 (11) | |
C9 | 1.0229 (7) | 0.3270 (3) | 0.2694 (2) | 0.0479 (11) | |
C10 | 0.9648 (7) | 0.3411 (3) | 0.1915 (2) | 0.0450 (11) | |
C11 | 1.1125 (8) | 0.3975 (3) | 0.1491 (3) | 0.0501 (11) | |
C12 | 1.0565 (8) | 0.4065 (3) | 0.0708 (2) | 0.0566 (12) | |
C13 | 0.7925 (8) | 0.3968 (3) | 0.0548 (3) | 0.0596 (13) | |
C14 | 0.7031 (7) | 0.3152 (3) | 0.0832 (2) | 0.0517 (11) | |
C15 | 0.7850 (7) | 0.3023 (3) | 0.1583 (3) | 0.0457 (11) | |
C16 | 0.7265 (8) | 0.2140 (3) | 0.2576 (3) | 0.0515 (12) | |
C17 | 0.5817 (8) | 0.1420 (3) | 0.2807 (3) | 0.0604 (13) | |
C18 | 0.6238 (9) | 0.1242 (3) | 0.3605 (3) | 0.0788 (16) | |
C19 | 0.8789 (9) | 0.1274 (3) | 0.3801 (3) | 0.0731 (15) | |
C20 | 0.9904 (8) | 0.2077 (3) | 0.3599 (3) | 0.0552 (12) | |
C21 | 0.9076 (7) | 0.2473 (3) | 0.2938 (3) | 0.0475 (11) | |
H2 | 0.3657 | 0.5289 | 0.2932 | 0.0707* | |
H3 | 0.1950 | 0.6266 | 0.3669 | 0.0716* | |
H5 | 0.7242 | 0.5987 | 0.5082 | 0.0702* | |
H6 | 0.8972 | 0.5024 | 0.4343 | 0.0667* | |
H9 | 1.1956 | 0.3215 | 0.2743 | 0.0575* | |
H12A | 1.1445 | 0.3655 | 0.0439 | 0.0679* | |
H12B | 1.1083 | 0.4602 | 0.0546 | 0.0679* | |
H13A | 0.7049 | 0.4413 | 0.0773 | 0.0715* | |
H13B | 0.7660 | 0.3997 | 0.0033 | 0.0715* | |
H14A | 0.5308 | 0.3143 | 0.0816 | 0.0620* | |
H14B | 0.7614 | 0.2710 | 0.0530 | 0.0620* | |
H17A | 0.6251 | 0.0942 | 0.2523 | 0.0725* | |
H17B | 0.4146 | 0.1533 | 0.2725 | 0.0725* | |
H18A | 0.5375 | 0.1640 | 0.3891 | 0.0946* | |
H18B | 0.5617 | 0.0701 | 0.3719 | 0.0946* | |
H19A | 0.9622 | 0.0831 | 0.3560 | 0.0877* | |
H19B | 0.8954 | 0.1191 | 0.4317 | 0.0877* | |
H8 | 1.046 (9) | 0.408 (3) | 0.364 (3) | 0.12 (2)* | |
H7 | 0.655 (7) | 0.435 (3) | 0.266 (3) | 0.061 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0885 (10) | 0.0694 (8) | 0.0646 (9) | 0.0114 (7) | 0.0153 (7) | −0.0112 (7) |
O1 | 0.0528 (17) | 0.0641 (18) | 0.047 (2) | −0.0088 (15) | −0.0037 (15) | 0.0049 (16) |
O2 | 0.062 (2) | 0.084 (3) | 0.052 (2) | −0.0199 (17) | −0.0020 (16) | 0.0004 (17) |
O3 | 0.069 (3) | 0.089 (3) | 0.053 (3) | 0.0059 (18) | −0.0130 (17) | 0.0064 (18) |
C1 | 0.055 (3) | 0.056 (3) | 0.035 (3) | −0.009 (3) | 0.005 (2) | −0.000 (2) |
C2 | 0.053 (3) | 0.076 (3) | 0.048 (3) | 0.007 (3) | −0.006 (3) | −0.008 (3) |
C3 | 0.052 (3) | 0.069 (3) | 0.057 (4) | 0.009 (3) | 0.001 (3) | −0.001 (3) |
C4 | 0.062 (3) | 0.051 (3) | 0.042 (3) | −0.004 (3) | 0.012 (3) | −0.004 (3) |
C5 | 0.063 (3) | 0.065 (3) | 0.048 (3) | −0.002 (3) | −0.008 (3) | −0.008 (3) |
C6 | 0.057 (3) | 0.060 (3) | 0.050 (4) | 0.011 (3) | −0.001 (3) | −0.003 (3) |
C7 | 0.050 (3) | 0.069 (3) | 0.038 (3) | −0.007 (3) | −0.005 (3) | −0.011 (3) |
C8 | 0.054 (3) | 0.057 (3) | 0.043 (3) | −0.005 (3) | −0.001 (3) | −0.005 (3) |
C9 | 0.048 (3) | 0.062 (3) | 0.033 (3) | 0.002 (2) | −0.0016 (19) | −0.005 (3) |
C10 | 0.051 (3) | 0.050 (3) | 0.034 (3) | 0.008 (2) | −0.000 (2) | 0.000 (2) |
C11 | 0.053 (3) | 0.057 (3) | 0.040 (3) | 0.007 (3) | 0.007 (3) | −0.002 (3) |
C12 | 0.066 (3) | 0.066 (3) | 0.038 (3) | −0.000 (3) | 0.002 (3) | 0.004 (3) |
C13 | 0.070 (4) | 0.071 (3) | 0.038 (3) | 0.005 (3) | −0.006 (3) | 0.003 (3) |
C14 | 0.052 (3) | 0.062 (3) | 0.041 (3) | 0.003 (3) | −0.001 (2) | −0.006 (3) |
C15 | 0.048 (3) | 0.053 (3) | 0.036 (3) | 0.004 (3) | 0.003 (2) | −0.004 (2) |
C16 | 0.061 (3) | 0.056 (3) | 0.038 (3) | 0.011 (3) | 0.003 (3) | 0.009 (3) |
C17 | 0.063 (3) | 0.059 (3) | 0.060 (4) | −0.007 (3) | 0.008 (3) | 0.002 (3) |
C18 | 0.084 (4) | 0.076 (4) | 0.076 (4) | −0.001 (3) | 0.010 (3) | 0.025 (3) |
C19 | 0.083 (4) | 0.073 (4) | 0.062 (4) | 0.011 (3) | 0.005 (3) | 0.020 (3) |
C20 | 0.062 (3) | 0.063 (3) | 0.041 (3) | 0.014 (3) | 0.007 (3) | −0.001 (3) |
C21 | 0.052 (3) | 0.053 (3) | 0.037 (3) | 0.010 (3) | 0.001 (2) | −0.002 (3) |
Cl1—C4 | 1.737 (5) | C17—C18 | 1.529 (7) |
O1—C15 | 1.377 (5) | C18—C19 | 1.481 (7) |
O1—C16 | 1.379 (6) | C19—C20 | 1.499 (7) |
O2—C11 | 1.228 (6) | C20—C21 | 1.461 (6) |
O3—C20 | 1.225 (6) | C2—H2 | 0.930 |
C1—C2 | 1.388 (6) | C3—H3 | 0.930 |
C1—C6 | 1.391 (6) | C5—H5 | 0.930 |
C1—C7 | 1.472 (6) | C6—H6 | 0.930 |
C2—C3 | 1.383 (7) | C7—H7 | 0.96 (4) |
C3—C4 | 1.368 (7) | C8—H8 | 1.06 (6) |
C4—C5 | 1.372 (7) | C9—H9 | 0.980 |
C5—C6 | 1.376 (6) | C12—H12A | 0.970 |
C7—C8 | 1.306 (7) | C12—H12B | 0.970 |
C8—C9 | 1.520 (6) | C13—H13A | 0.970 |
C9—C10 | 1.501 (6) | C13—H13B | 0.970 |
C9—C21 | 1.520 (6) | C14—H14A | 0.970 |
C10—C11 | 1.468 (6) | C14—H14B | 0.970 |
C10—C15 | 1.341 (6) | C17—H17A | 0.970 |
C11—C12 | 1.495 (6) | C17—H17B | 0.970 |
C12—C13 | 1.522 (6) | C18—H18A | 0.970 |
C13—C14 | 1.515 (6) | C18—H18B | 0.970 |
C14—C15 | 1.483 (6) | C19—H19A | 0.970 |
C16—C17 | 1.491 (6) | C19—H19B | 0.970 |
C16—C21 | 1.335 (6) | ||
O1···C9 | 2.881 (5) | C11···H18Bvi | 3.0007 |
O2···C8 | 3.317 (6) | C12···H12Bxi | 3.3132 |
O2···C9 | 2.842 (5) | C12···H13Bxi | 3.5843 |
O2···C15 | 3.531 (5) | C12···H14Aii | 3.0675 |
O3···C8 | 3.165 (6) | C12···H18Axii | 3.5651 |
O3···C9 | 2.845 (5) | C12···H18Bvi | 2.9442 |
O3···C16 | 3.521 (6) | C12···H19Bxii | 3.2416 |
O3···C18 | 3.556 (6) | C13···H12Bxi | 3.1400 |
C1···C4 | 2.777 (6) | C13···H18Axii | 3.5169 |
C2···C5 | 2.752 (7) | C13···H18Bvi | 3.2365 |
C3···C6 | 2.749 (6) | C13···H19Bv | 3.2044 |
C6···C8 | 3.034 (6) | C14···H12Aiv | 3.3275 |
C7···C10 | 2.962 (6) | C14···H19Bv | 3.4699 |
C7···C15 | 3.581 (7) | C16···H9iv | 3.4764 |
C7···C21 | 3.275 (6) | C17···H2viii | 3.4042 |
C8···C11 | 3.296 (7) | C17···H3viii | 3.1582 |
C8···C15 | 3.455 (6) | C18···H12Axiii | 3.4111 |
C8···C16 | 3.389 (6) | C18···H12Bxiv | 3.3639 |
C8···C20 | 3.170 (6) | C18···H13Axiv | 3.3343 |
C10···C13 | 2.862 (6) | C18···H13Bxiii | 3.3548 |
C10···C16 | 2.756 (6) | C19···H12Axiii | 3.3187 |
C11···C14 | 2.930 (6) | C19···H13Axiv | 3.1656 |
C12···C15 | 2.804 (6) | C19···H13Biii | 3.1845 |
C15···C21 | 2.757 (6) | C20···H13Biii | 3.5396 |
C16···C19 | 2.809 (7) | C20···H17Bii | 3.0220 |
C17···C20 | 2.929 (7) | C20···H18Aii | 3.2042 |
C18···C21 | 2.847 (7) | C21···H17Bii | 3.2623 |
Cl1···O3i | 3.359 (4) | H2···O2iv | 2.7005 |
Cl1···C20i | 3.467 (5) | H2···C8iv | 3.2630 |
O2···C2ii | 3.565 (6) | H2···C17vii | 3.4042 |
O2···C7ii | 3.588 (6) | H2···H9iv | 3.5252 |
O2···C14ii | 3.521 (5) | H2···H17Avii | 3.0753 |
O2···C15ii | 3.568 (5) | H2···H17Avi | 3.1724 |
O3···Cl1i | 3.359 (4) | H2···H17Bvii | 2.8393 |
O3···C14iii | 3.599 (5) | H2···H19Avi | 3.0672 |
O3···C18ii | 3.317 (6) | H2···H8iv | 2.9741 |
C2···O2iv | 3.565 (6) | H3···O1vii | 2.9310 |
C3···C6iv | 3.557 (6) | H3···C6iv | 3.1309 |
C5···C5i | 3.466 (6) | H3···C17vii | 3.1582 |
C5···C6i | 3.598 (6) | H3···H6iv | 2.9096 |
C6···C3ii | 3.557 (6) | H3···H14Avii | 3.4449 |
C6···C5i | 3.598 (6) | H3···H17Avii | 2.8986 |
C7···O2iv | 3.588 (6) | H3···H17Bvii | 2.6940 |
C14···O2iv | 3.521 (5) | H5···Cl1ii | 3.5138 |
C14···O3v | 3.599 (5) | H5···O3x | 3.2704 |
C15···O2iv | 3.568 (5) | H5···H6x | 2.8933 |
C18···O3iv | 3.317 (6) | H5···H14Bvi | 3.0276 |
C20···Cl1i | 3.467 (5) | H5···H8x | 2.6944 |
Cl1···H3 | 2.7686 | H6···Cl1i | 3.4592 |
Cl1···H5 | 2.8101 | H6···C3ii | 3.0969 |
O1···H14A | 2.4421 | H6···C4ii | 3.5932 |
O1···H14B | 2.7084 | H6···C4i | 3.5306 |
O1···H17A | 2.6866 | H6···C5x | 3.4489 |
O1···H17B | 2.4731 | H6···C6x | 3.3615 |
O1···H7 | 3.38 (4) | H6···H3ii | 2.9096 |
O2···H9 | 2.6141 | H6···H5x | 2.8933 |
O2···H12A | 2.8131 | H6···H6x | 2.6985 |
O2···H12B | 2.5062 | H9···O1ii | 3.2165 |
O3···H9 | 2.6434 | H9···C16ii | 3.4764 |
O3···H19A | 2.8377 | H9···H2ii | 3.5252 |
O3···H19B | 2.5037 | H9···H17Bii | 3.0027 |
O3···H8 | 2.88 (5) | H9···H7ii | 3.1772 |
C1···H3 | 3.2526 | H12A···Cl1xiv | 3.0610 |
C1···H5 | 3.2525 | H12A···C14ii | 3.3275 |
C1···H8 | 2.72 (5) | H12A···C18xii | 3.4111 |
C2···H6 | 3.2173 | H12A···C19xii | 3.3187 |
C2···H7 | 2.51 (4) | H12A···H13Aii | 3.4409 |
C3···H5 | 3.2211 | H12A···H14Aii | 2.4297 |
C4···H2 | 3.2107 | H12A···H18Axii | 2.9741 |
C4···H6 | 3.2087 | H12A···H18Bxii | 3.3927 |
C5···H3 | 3.2214 | H12A···H19Bxii | 2.5322 |
C6···H2 | 3.2183 | H12B···C12xi | 3.3132 |
C6···H8 | 2.74 (5) | H12B···C13xi | 3.1400 |
C6···H7 | 3.29 (4) | H12B···C18vi | 3.3639 |
C7···H2 | 2.6112 | H12B···H12Bxi | 2.6951 |
C7···H6 | 2.6827 | H12B···H13Aii | 3.3961 |
C7···H9 | 3.2300 | H12B···H13Axi | 3.1116 |
C8···H6 | 2.7711 | H12B···H13Bxi | 2.6186 |
C9···H7 | 2.71 (4) | H12B···H14Aii | 3.3965 |
C10···H12A | 2.9504 | H12B···H18Avi | 3.5734 |
C10···H12B | 3.2984 | H12B···H18Bvi | 2.4456 |
C10···H13A | 3.0459 | H12B···H18Bxii | 3.4387 |
C10···H14A | 3.2078 | H12B···H19Aix | 3.5456 |
C10···H14B | 3.0353 | H12B···H19Bxii | 3.0834 |
C10···H8 | 3.42 (6) | H13A···O2iv | 3.0247 |
C10···H7 | 2.70 (4) | H13A···C18vi | 3.3343 |
C11···H9 | 2.6738 | H13A···C19vi | 3.1656 |
C11···H13A | 2.7447 | H13A···H12Aiv | 3.4409 |
C11···H13B | 3.3340 | H13A···H12Biv | 3.3961 |
C11···H14B | 3.3630 | H13A···H12Bxi | 3.1116 |
C11···H7 | 3.42 (4) | H13A···H18Bvi | 2.6469 |
C12···H14A | 3.3231 | H13A···H19Avi | 2.7840 |
C12···H14B | 2.7793 | H13A···H19Bvi | 2.9537 |
C14···H12A | 2.7165 | H13A···H19Bv | 3.3601 |
C14···H12B | 3.3254 | H13B···O3v | 3.0736 |
C15···H9 | 3.1710 | H13B···C12xi | 3.5843 |
C15···H12A | 3.1122 | H13B···C18xii | 3.3548 |
C15···H13A | 2.7537 | H13B···C19v | 3.1845 |
C15···H13B | 3.2884 | H13B···C20v | 3.5396 |
C15···H7 | 3.03 (4) | H13B···H12Bxi | 2.6186 |
C16···H9 | 3.1811 | H13B···H18Axii | 2.8134 |
C16···H18A | 2.7863 | H13B···H18Bxii | 2.9969 |
C16···H18B | 3.2940 | H13B···H19Av | 3.2336 |
C16···H19A | 3.1021 | H13B···H19Bv | 2.4891 |
C17···H19A | 2.7286 | H14A···Cl1viii | 3.1848 |
C17···H19B | 3.3306 | H14A···O2iv | 2.9806 |
C19···H17A | 2.8197 | H14A···C11iv | 2.9919 |
C19···H17B | 3.3132 | H14A···C12iv | 3.0675 |
C20···H9 | 2.7008 | H14A···H3viii | 3.4449 |
C20···H17A | 3.4068 | H14A···H12Aiv | 2.4297 |
C20···H18A | 2.7016 | H14A···H12Biv | 3.3965 |
C20···H18B | 3.2989 | H14A···H19Bv | 3.0826 |
C20···H8 | 3.28 (5) | H14B···Cl1viii | 3.5700 |
C21···H17A | 3.0540 | H14B···Cl1xiv | 3.0390 |
C21···H17B | 3.1924 | H14B···O3v | 2.9866 |
C21···H18A | 3.0528 | H14B···C4xiv | 2.9960 |
C21···H19A | 2.9276 | H14B···C5xiv | 3.1038 |
C21···H19B | 3.3026 | H14B···H5xiv | 3.0276 |
C21···H8 | 3.03 (5) | H14B···H18Axii | 3.5788 |
C21···H7 | 3.40 (4) | H14B···H19Bv | 3.5342 |
H2···H3 | 2.3074 | H17A···C1xiv | 2.7895 |
H2···H7 | 2.2949 | H17A···C2xiv | 3.0787 |
H5···H6 | 2.3001 | H17A···C3viii | 3.5763 |
H6···H8 | 2.1765 | H17A···C6xiv | 3.4635 |
H6···H7 | 3.5875 | H17A···C7xiv | 2.8328 |
H9···H8 | 2.3468 | H17A···C8xiv | 3.5036 |
H9···H7 | 3.5592 | H17A···H2viii | 3.0753 |
H12A···H13A | 2.8331 | H17A···H2xiv | 3.1724 |
H12A···H13B | 2.3250 | H17A···H3viii | 2.8986 |
H12A···H14B | 2.6532 | H17A···H7xiv | 2.8962 |
H12B···H13A | 2.3297 | H17B···O3iv | 3.0658 |
H12B···H13B | 2.3630 | H17B···C2viii | 3.3599 |
H13A···H14A | 2.2882 | H17B···C3viii | 3.2863 |
H13A···H14B | 2.8251 | H17B···C9iv | 3.5857 |
H13A···H7 | 3.5115 | H17B···C20iv | 3.0220 |
H13B···H14A | 2.4098 | H17B···C21iv | 3.2623 |
H13B···H14B | 2.2880 | H17B···H2viii | 2.8393 |
H17A···H18A | 2.8272 | H17B···H3viii | 2.6940 |
H17A···H18B | 2.2832 | H17B···H9iv | 3.0027 |
H17A···H19A | 2.7061 | H17B···H19Aiv | 3.1948 |
H17B···H18A | 2.2790 | H18A···Cl1i | 3.2869 |
H17B···H18B | 2.4325 | H18A···O3iv | 2.4963 |
H18A···H19A | 2.7983 | H18A···C12xiii | 3.5651 |
H18A···H19B | 2.2821 | H18A···C13xiii | 3.5169 |
H18B···H19A | 2.2829 | H18A···C20iv | 3.2042 |
H18B···H19B | 2.3207 | H18A···H12Axiii | 2.9741 |
H8···H7 | 2.89 (7) | H18A···H12Bxiv | 3.5734 |
Cl1···H5iv | 3.5138 | H18A···H13Bxiii | 2.8134 |
Cl1···H6i | 3.4592 | H18A···H14Bxiii | 3.5788 |
Cl1···H12Avi | 3.0610 | H18A···H19Aiv | 3.5469 |
Cl1···H14Avii | 3.1848 | H18B···O2xiv | 3.0768 |
Cl1···H14Bvii | 3.5700 | H18B···C11xiv | 3.0007 |
Cl1···H14Bvi | 3.0390 | H18B···C12xiv | 2.9442 |
Cl1···H18Ai | 3.2869 | H18B···C13xiv | 3.2365 |
Cl1···H19Bi | 3.5522 | H18B···H12Axiii | 3.3927 |
Cl1···H8i | 3.48 (6) | H18B···H12Bxiv | 2.4456 |
O1···H3viii | 2.9310 | H18B···H12Bxiii | 3.4387 |
O1···H9iv | 3.2165 | H18B···H13Axiv | 2.6469 |
O2···H2ii | 2.7005 | H18B···H13Bxiii | 2.9969 |
O2···H13Aii | 3.0247 | H18B···H19Aiv | 3.3917 |
O2···H14Aii | 2.9806 | H19A···O2xv | 2.8956 |
O2···H18Bvi | 3.0768 | H19A···H2xiv | 3.0672 |
O2···H19Aix | 2.8956 | H19A···H12Bxv | 3.5456 |
O2···H7ii | 2.67 (4) | H19A···H13Axiv | 2.7840 |
O3···H5x | 3.2704 | H19A···H13Biii | 3.2336 |
O3···H13Biii | 3.0736 | H19A···H17Bii | 3.1948 |
O3···H14Biii | 2.9866 | H19A···H18Aii | 3.5469 |
O3···H17Bii | 3.0658 | H19A···H18Bii | 3.3917 |
O3···H18Aii | 2.4963 | H19A···H7xiv | 3.3714 |
C1···H17Avi | 2.7895 | H19B···Cl1i | 3.5522 |
C2···H17Avi | 3.0787 | H19B···C12xiii | 3.2416 |
C2···H17Bvii | 3.3599 | H19B···C13iii | 3.2044 |
C2···H8iv | 3.15 (5) | H19B···C14iii | 3.4699 |
C3···H6iv | 3.0969 | H19B···H12Axiii | 2.5322 |
C3···H17Avii | 3.5763 | H19B···H12Bxiii | 3.0834 |
C3···H17Bvii | 3.2863 | H19B···H13Axiv | 2.9537 |
C3···H8iv | 3.54 (5) | H19B···H13Aiii | 3.3601 |
C4···H6iv | 3.5932 | H19B···H13Biii | 2.4891 |
C4···H6i | 3.5306 | H19B···H14Aiii | 3.0826 |
C4···H14Bvi | 2.9960 | H19B···H14Biii | 3.5342 |
C5···H6x | 3.4489 | H8···Cl1i | 3.48 (6) |
C5···H14Bvi | 3.1038 | H8···C2ii | 3.15 (5) |
C5···H8x | 3.59 (6) | H8···C3ii | 3.54 (5) |
C6···H3ii | 3.1309 | H8···C5x | 3.59 (6) |
C6···H6x | 3.3615 | H8···H2ii | 2.9741 |
C6···H17Avi | 3.4635 | H8···H5x | 2.6944 |
C7···H17Avi | 2.8328 | H7···O2iv | 2.67 (4) |
C8···H2ii | 3.2630 | H7···H9iv | 3.1772 |
C8···H17Avi | 3.5036 | H7···H17Avi | 2.8962 |
C9···H17Bii | 3.5857 | H7···H19Avi | 3.3714 |
C11···H14Aii | 2.9919 | ||
C15—O1—C16 | 117.9 (3) | C4—C3—H3 | 120.295 |
C2—C1—C6 | 117.4 (4) | C4—C5—H5 | 120.343 |
C2—C1—C7 | 119.5 (4) | C6—C5—H5 | 120.335 |
C6—C1—C7 | 123.1 (4) | C1—C6—H6 | 119.226 |
C1—C2—C3 | 121.3 (4) | C5—C6—H6 | 119.214 |
C2—C3—C4 | 119.4 (4) | C1—C7—H7 | 110 (3) |
Cl1—C4—C3 | 118.7 (4) | C8—C7—H7 | 122 (3) |
Cl1—C4—C5 | 120.4 (4) | C7—C8—H8 | 118 (3) |
C3—C4—C5 | 120.9 (4) | C9—C8—H8 | 117 (3) |
C4—C5—C6 | 119.3 (4) | C8—C9—H9 | 108.517 |
C1—C6—C5 | 121.6 (4) | C10—C9—H9 | 108.517 |
C1—C7—C8 | 127.8 (5) | C21—C9—H9 | 108.517 |
C7—C8—C9 | 124.8 (4) | C11—C12—H12A | 109.090 |
C8—C9—C10 | 113.6 (4) | C11—C12—H12B | 109.095 |
C8—C9—C21 | 108.6 (4) | C13—C12—H12A | 109.096 |
C10—C9—C21 | 109.0 (4) | C13—C12—H12B | 109.096 |
C9—C10—C11 | 119.3 (4) | H12A—C12—H12B | 107.839 |
C9—C10—C15 | 122.2 (4) | C12—C13—H13A | 109.587 |
C11—C10—C15 | 118.4 (4) | C12—C13—H13B | 109.587 |
O2—C11—C10 | 120.7 (4) | C14—C13—H13A | 109.580 |
O2—C11—C12 | 121.5 (4) | C14—C13—H13B | 109.577 |
C10—C11—C12 | 117.7 (4) | H13A—C13—H13B | 108.127 |
C11—C12—C13 | 112.5 (4) | C13—C14—H14A | 109.571 |
C12—C13—C14 | 110.3 (4) | C13—C14—H14B | 109.570 |
C13—C14—C15 | 110.4 (4) | C15—C14—H14A | 109.565 |
O1—C15—C10 | 122.4 (4) | C15—C14—H14B | 109.565 |
O1—C15—C14 | 111.0 (4) | H14A—C14—H14B | 108.112 |
C10—C15—C14 | 126.7 (4) | C16—C17—H17A | 109.647 |
O1—C16—C17 | 110.9 (4) | C16—C17—H17B | 109.641 |
O1—C16—C21 | 122.8 (4) | C18—C17—H17A | 109.632 |
C17—C16—C21 | 126.3 (4) | C18—C17—H17B | 109.638 |
C16—C17—C18 | 110.1 (4) | H17A—C17—H17B | 108.161 |
C17—C18—C19 | 112.4 (5) | C17—C18—H18A | 109.137 |
C18—C19—C20 | 112.0 (4) | C17—C18—H18B | 109.133 |
O3—C20—C19 | 121.7 (4) | C19—C18—H18A | 109.133 |
O3—C20—C21 | 120.6 (4) | C19—C18—H18B | 109.127 |
C19—C20—C21 | 117.6 (4) | H18A—C18—H18B | 107.854 |
C9—C21—C16 | 121.5 (4) | C18—C19—H19A | 109.215 |
C9—C21—C20 | 119.5 (4) | C18—C19—H19B | 109.211 |
C16—C21—C20 | 119.0 (4) | C20—C19—H19A | 109.213 |
C1—C2—H2 | 119.337 | C20—C19—H19B | 109.201 |
C3—C2—H2 | 119.331 | H19A—C19—H19B | 107.906 |
C2—C3—H3 | 120.285 | ||
C15—O1—C16—C17 | −169.7 (3) | C9—C10—C11—C12 | 176.9 (3) |
C15—O1—C16—C21 | 11.3 (6) | C9—C10—C15—O1 | −2.6 (6) |
C16—O1—C15—C10 | −13.3 (5) | C9—C10—C15—C14 | 176.0 (4) |
C16—O1—C15—C14 | 167.9 (3) | C11—C10—C15—O1 | 175.7 (4) |
C2—C1—C6—C5 | 1.0 (6) | C11—C10—C15—C14 | −5.7 (6) |
C6—C1—C2—C3 | −0.6 (6) | C15—C10—C11—O2 | −179.0 (4) |
C2—C1—C7—C8 | −177.1 (4) | C15—C10—C11—C12 | −1.4 (6) |
C7—C1—C2—C3 | 177.7 (4) | O2—C11—C12—C13 | −150.2 (4) |
C6—C1—C7—C8 | 1.0 (7) | C10—C11—C12—C13 | 32.2 (5) |
C7—C1—C6—C5 | −177.2 (4) | C11—C12—C13—C14 | −55.7 (5) |
C1—C2—C3—C4 | −1.6 (7) | C12—C13—C14—C15 | 47.7 (4) |
C2—C3—C4—Cl1 | −175.5 (4) | C13—C14—C15—O1 | 160.2 (3) |
C2—C3—C4—C5 | 3.4 (7) | C13—C14—C15—C10 | −18.6 (6) |
Cl1—C4—C5—C6 | 175.9 (3) | O1—C16—C17—C18 | −164.2 (3) |
C3—C4—C5—C6 | −3.0 (7) | O1—C16—C21—C9 | 6.5 (6) |
C4—C5—C6—C1 | 0.7 (6) | O1—C16—C21—C20 | −175.8 (3) |
C1—C7—C8—C9 | 175.5 (4) | C17—C16—C21—C9 | −172.5 (4) |
C7—C8—C9—C10 | 32.5 (6) | C17—C16—C21—C20 | 5.3 (7) |
C7—C8—C9—C21 | −88.9 (5) | C21—C16—C17—C18 | 14.8 (6) |
C8—C9—C10—C11 | 78.4 (5) | C16—C17—C18—C19 | −44.7 (5) |
C8—C9—C10—C15 | −103.2 (4) | C17—C18—C19—C20 | 55.4 (5) |
C8—C9—C21—C16 | 104.4 (4) | C18—C19—C20—O3 | 146.9 (5) |
C8—C9—C21—C20 | −73.3 (5) | C18—C19—C20—C21 | −35.1 (6) |
C10—C9—C21—C16 | −19.8 (5) | O3—C20—C21—C9 | 0.6 (6) |
C10—C9—C21—C20 | 162.5 (3) | O3—C20—C21—C16 | −177.2 (4) |
C21—C9—C10—C11 | −160.4 (3) | C19—C20—C21—C9 | −177.4 (4) |
C21—C9—C10—C15 | 18.0 (5) | C19—C20—C21—C16 | 4.8 (6) |
C9—C10—C11—O2 | −0.7 (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) x−1, y, z; (v) x−1/2, −y+1/2, z−1/2; (vi) −x+3/2, y+1/2, −z+1/2; (vii) −x+1/2, y+1/2, −z+1/2; (viii) −x+1/2, y−1/2, −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, z−1/2; (xiii) x−1/2, −y+1/2, z+1/2; (xiv) −x+3/2, y−1/2, −z+1/2; (xv) −x+5/2, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18A···O3iv | 0.97 | 2.50 | 3.316 (6) | 142 |
Symmetry code: (iv) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C21H19ClO3 |
Mr | 354.83 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 5.6262 (7), 16.273 (2), 18.570 (3) |
β (°) | 90.125 (4) |
V (Å3) | 1700.2 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.30 × 0.02 × 0.02 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Rigaku, 1995) |
Tmin, Tmax | 0.490, 0.995 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 13165, 3066, 1304 |
Rint | 0.130 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.157, 0.95 |
No. of reflections | 3066 |
No. of parameters | 234 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18A···O3i | 0.970 | 2.4963 | 3.316 (6) | 142.00 |
Symmetry code: (i) x−1, y, z. |
Acknowledgements
Fiancial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.
References
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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.
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.