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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 64| Part 1| January 2008| Page o328
https://doi.org/10.1107/S1600536807066925

8-Eth­­oxy-3-(4-iso­propyl­benzyl­­idene)-6-methyl­chroman-4-one

A. Marx,a V. Manivannan,a* R. Suresh,b Charles C. Kanagamc and B. Sridhard

aDepartment of Physics, Presidency College, Chennai 600 005, India, bDepartment of Chemistry, Presidency College, Chennai 600 005, India, cDepartment of Chemistry, Valliammai Engineering College, Kattankulathur, Chennai, India, and dIndian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India
*Correspondence e-mail: manivan_1999@yahoo.com

(Received 16 November 2007; accepted 14 December 2007; online 21 December 2007)

In the title compound, C22H24O3, the non-fused benzene ring makes a dihedral angle of 52.56 (7)° with the benzene ring of the chromanone unit. The mol­ecular structure is stabilized by a weak intra­molecular C—H⋯O inter­action and the crystal packing is stabilized by weak inter­molecular C—H⋯O inter­actions. The isopropyl group is disordered over two positions, with site occupancies of 0.48/0.52.

Related literature

For related literature, see: Kang et al. (2004[Kang, J. G., Shin, S. Y., Kim, M. J., Bajpai, V., Maheshwari, D. K. & Kang, S. C. (2004). J. Antibiot. 57, 726-731.]); Marx et al. (2007[Marx, A., Manivannan, V., Suresh, R., Kanagam, C. C. & Büyükgüngör, O. (2007). Acta Cryst. E63, o4383.]); Puviarasan et al. (1998[Puviarasan, K., Govindasamy, L., Velmurugan, D., Shanmuga Sundara Raj, S., Shanmuga Sundaram, M., Raghunathan, R. & Fun, H.-K. (1998). Acta Cryst. C54, 961-963.]); Tillekeratne et al. (2001[Tillekeratne, L. M., Sherette, A., Grossman, P., Hupe, L., Hupe, D. & Hudson, R. A. (2001). Bioorg. Med. Chem. Lett. 11, 2763-2764.]); Nissa et al. (2001[Nissa, M. N., Rajakannan, V., Kim, M.-J. & Velmurugan, D. (2001). Acta Cryst. E57, o1230-o1232.]); Schollmeyer et al. (2005[Schollmeyer, D., Kammerer, B., Peifer, C. & Laufer, S. (2005). Acta Cryst. E61, o868-o869.]). A related compound has been reported by Marx et al. (2007[Marx, A., Manivannan, V., Suresh, R., Kanagam, C. C. & Büyükgüngör, O. (2007). Acta Cryst. E63, o4383.]).

[Scheme 1]

Experimental

Crystal data

  • C22H24O3

  • Mr = 336.41

  • Monoclinic, P 21 /n

  • a = 10.3568 (9) Å

  • b = 16.8154 (15) Å

  • c = 10.8962 (10) Å

  • β = 99.873 (1)°

  • V = 1869.5 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 295 (2) K

  • 0.22 × 0.18 × 0.16 mm
Data collection

  • Bruker SMART APEX area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.983, Tmax = 0.988

  • 21105 measured reflections

  • 4385 independent reflections

  • 3220 reflections with I > 2σ(I)

  • Rint = 0.026
Refinement

  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.158

  • S = 1.02

  • 4385 reflections

  • 256 parameters

  • 4 restraints

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.14 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C9—H9A⋯O2i 0.97 2.60 3.407 (2) 141
C10—H10⋯O2 0.93 2.47 2.823 (2) 103
Symmetry code: (i) -x+2, -y, -z+2.

Data collection: SMART (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807066925/bq2050sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807066925/bq2050Isup2.hkl

checkCIF report


Comment top

The Chromanone moiety present in the title compound consisting of the pyrone ring and benzene ring plays an important role in many areas of medicines such as inhibition of HIV replication (Tillekeratne et al., 2001).

The geometric parameters in (I) agree with the reported values of similar structure (Puviarasan et al., 1998; Schollmeyer et al., 2005; Nissa et al., 2001). The chromanone moiety consists of one benzene ring fused with a six membered heterocyclic ring which adopts a half-chair conformation. The C11—C16 benzene ring makes a dihedral angle of 52.56 (7)° with the benzene ring of chromanone unit.

The molecular structure is stabilized by weak intramolecular C—H···O interaction and the crystal packing is stabilized by weak intermolecular C—H···O interaction (Table 1.).

The methyl and aromatic C atoms in the ligand are disordered over two positions each with the site occupancy factors of 0.520 (10) [for C17, C18, C19] and 0.480 (10) for [C171, C181, C191].

Related literature top

For related literature, see: Kang et al. (2004); Marx et al. (2007); Puviarasan et al. (1998); Tillekeratne et al. (2001); Nissa et al. (2001); Schollmeyer et al. (2005). A related compound has been reported by Marx et al. (2007).

Experimental top

Baylis-Hillman reaction of p-isopropyl benzaldehyde with methyl acrylate afforded methyl-3-hydroxy-3-(p-isopropyl phenyl-)-2-methylene propanoate. This ester was converted to methyl-(2-Z)-2-bromomethyl-3-(p-isopropyl phenyl)-prop-2-enoate on treatment with hydrobromic acid in presence of concentrated sulfuric acid. The resulting propenoate was treated with 2-ethoxy-4-methyl phenol in presence of potassium carbonate and acetone to get methyl-3-(p-isopropyl phenyl)-2-(2-ethoxy-4-methyl)-phenoxy methyl-prop-2-enoate. The phenoxy propenoate was hydrolysed by alkali solution to get the prop-2-enoic acid. Cyclization of the acid on treatment with trifluoro acetic anhydride in dichloromethane resulted in 3-(4-isopropyl) benzylidine-8-ethoxy-6-methyl chroman-4-one.

Refinement top

The site occupancy factors for disordered C atoms were refined as 0.520 (10) [for C17, C18, C19] and 0.480 (10) for [C171, C181, C191]. during anisotropic refinement. C17—C19, C17—C18, C171–181 C171–191 distances were restrained to 1.55 (1). H atoms were positioned geometrically and refined using riding model with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.97Å and Uiso(H) = 1.2Ueq(C) for CH2, C—H = 0.96Å and Uiso(H) = 1.5Ueq(C) for CH3.

Structure description top

The Chromanone moiety present in the title compound consisting of the pyrone ring and benzene ring plays an important role in many areas of medicines such as inhibition of HIV replication (Tillekeratne et al., 2001).

The geometric parameters in (I) agree with the reported values of similar structure (Puviarasan et al., 1998; Schollmeyer et al., 2005; Nissa et al., 2001). The chromanone moiety consists of one benzene ring fused with a six membered heterocyclic ring which adopts a half-chair conformation. The C11—C16 benzene ring makes a dihedral angle of 52.56 (7)° with the benzene ring of chromanone unit.

The molecular structure is stabilized by weak intramolecular C—H···O interaction and the crystal packing is stabilized by weak intermolecular C—H···O interaction (Table 1.).

The methyl and aromatic C atoms in the ligand are disordered over two positions each with the site occupancy factors of 0.520 (10) [for C17, C18, C19] and 0.480 (10) for [C171, C181, C191].

For related literature, see: Kang et al. (2004); Marx et al. (2007); Puviarasan et al. (1998); Tillekeratne et al. (2001); Nissa et al. (2001); Schollmeyer et al. (2005). A related compound has been reported by Marx et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
8-Ethoxy-3-(4-isopropylbenzylidene)-6-methylchroman-4-one top
Crystal data top
C22H24O3Z = 4
Mr = 336.41F(000) = 720
Monoclinic, P21/nDx = 1.195 Mg m−3
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 10.3568 (9) Åθ = 1.9–27.2°
b = 16.8154 (15) ŵ = 0.08 mm−1
c = 10.8962 (10) ÅT = 295 K
β = 99.873 (1)°Block, colourless
V = 1869.5 (3) Å30.22 × 0.18 × 0.16 mm
Data collection top
Bruker SMART APEX area-detector
diffractometer		4385 independent reflections
Radiation source: fine-focus sealed tube3220 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω and φ scansθmax = 28.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→13
Tmin = 0.983, Tmax = 0.988k = −21→21
21105 measured reflectionsl = −14→14
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0767P)2 + 0.3281P]
where P = (Fo2 + 2Fc2)/3
4385 reflections(Δ/σ)max < 0.001
256 parametersΔρmax = 0.23 e Å−3
4 restraintsΔρmin = −0.14 e Å−3
Crystal data top
C22H24O3V = 1869.5 (3) Å3
Mr = 336.41Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.3568 (9) ŵ = 0.08 mm−1
b = 16.8154 (15) ÅT = 295 K
c = 10.8962 (10) Å0.22 × 0.18 × 0.16 mm
β = 99.873 (1)°
Data collection top
Bruker SMART APEX area-detector
diffractometer		4385 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3220 reflections with I > 2σ(I)
Tmin = 0.983, Tmax = 0.988Rint = 0.026
21105 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0544 restraints
wR(F2) = 0.158H-atom parameters constrained
S = 1.02Δρmax = 0.23 e Å−3
4385 reflectionsΔρmin = −0.14 e Å−3
256 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C11.16222 (14)0.18147 (9)1.10909 (13)0.0528 (3)
C21.27835 (14)0.22634 (9)1.13210 (14)0.0554 (4)
C31.38353 (15)0.19764 (10)1.21563 (14)0.0607 (4)
H31.46070.22701.23040.073*
C41.37726 (16)0.12575 (10)1.27856 (15)0.0630 (4)
C51.26264 (17)0.08359 (10)1.25682 (15)0.0636 (4)
H51.25680.03611.29920.076*
C61.15337 (15)0.11036 (9)1.17194 (14)0.0555 (4)
C71.02883 (16)0.06564 (9)1.15305 (14)0.0587 (4)
C80.92415 (15)0.09672 (9)1.05370 (14)0.0568 (4)
C90.96801 (16)0.15548 (10)0.96569 (15)0.0631 (4)
H9A1.00680.12680.90390.076*
H9B0.89190.18370.92240.076*
C100.80031 (16)0.07161 (10)1.04848 (15)0.0621 (4)
H100.78770.03511.10940.075*
C110.68243 (16)0.09345 (10)0.96090 (16)0.0621 (4)
C120.56167 (19)0.09445 (13)1.0015 (2)0.0835 (6)
H120.55740.08041.08330.100*
C130.4489 (2)0.11585 (16)0.9224 (3)0.1030 (8)
H130.37020.11660.95250.124*
C140.4489 (2)0.13620 (13)0.7997 (2)0.0946 (7)
C150.5682 (2)0.13326 (12)0.7588 (2)0.0844 (6)
H150.57140.14610.67630.101*
C160.68203 (18)0.11198 (11)0.83633 (17)0.0713 (5)
H160.76010.10990.80500.086*
C170.3423 (5)0.1672 (3)0.6930 (5)0.0724 (14)0.520 (10)
H170.38050.18420.62090.087*0.520 (10)
C180.2693 (9)0.2337 (4)0.7420 (8)0.091 (2)0.520 (10)
H18A0.32600.27890.75960.136*0.520 (10)
H18B0.24030.21680.81690.136*0.520 (10)
H18C0.19480.24800.68070.136*0.520 (10)
C190.2513 (8)0.0950 (5)0.6613 (10)0.107 (3)0.520 (10)
H19A0.29940.05210.63230.160*0.520 (10)
H19B0.17920.10940.59740.160*0.520 (10)
H19C0.21840.07840.73450.160*0.520 (10)
C1710.3016 (5)0.1501 (3)0.7409 (6)0.0780 (16)0.480 (10)
H1710.23870.12930.79050.094*0.480 (10)
C1810.2898 (16)0.2399 (6)0.7148 (16)0.176 (7)0.480 (10)
H18D0.30350.26840.79220.263*0.480 (10)
H18E0.20390.25150.66960.263*0.480 (10)
H18F0.35450.25570.66620.263*0.480 (10)
C1910.2836 (11)0.1179 (9)0.6070 (8)0.150 (5)0.480 (10)
H19D0.28920.06090.60900.225*0.480 (10)
H19E0.35100.13900.56580.225*0.480 (10)
H19F0.19930.13370.56260.225*0.480 (10)
C201.4972 (2)0.09598 (14)1.36590 (19)0.0858 (6)
H20A1.47130.05681.42100.129*
H20B1.53900.13971.41380.129*
H20C1.55730.07261.31830.129*
C221.39808 (17)0.33615 (11)1.06840 (18)0.0725 (5)
H22A1.46090.30151.03850.087*
H22B1.43400.35251.15270.087*
C231.3708 (2)0.40699 (12)0.9860 (2)0.0940 (7)
H23A1.33250.39020.90360.141*
H23B1.45120.43480.98300.141*
H23C1.31110.44171.01830.141*
O11.06117 (10)0.21232 (6)1.02605 (10)0.0640 (3)
O21.01289 (13)0.00744 (8)1.21616 (12)0.0782 (4)
O31.27649 (10)0.29549 (7)1.06605 (11)0.0669 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0486 (8)0.0529 (8)0.0538 (8)0.0013 (6)−0.0002 (6)−0.0003 (6)
C20.0514 (8)0.0528 (8)0.0596 (8)−0.0002 (6)0.0030 (6)−0.0019 (6)
C30.0490 (8)0.0660 (9)0.0636 (9)−0.0004 (7)−0.0003 (7)−0.0083 (7)
C40.0599 (9)0.0664 (9)0.0580 (9)0.0099 (7)−0.0029 (7)−0.0024 (7)
C50.0696 (10)0.0583 (9)0.0588 (9)0.0072 (7)−0.0005 (7)0.0059 (7)
C60.0576 (8)0.0535 (8)0.0535 (8)0.0008 (6)0.0037 (6)0.0002 (6)
C70.0636 (9)0.0543 (8)0.0570 (8)−0.0022 (7)0.0067 (7)0.0036 (7)
C80.0577 (9)0.0546 (8)0.0557 (8)−0.0063 (6)0.0028 (6)−0.0002 (6)
C90.0585 (9)0.0649 (9)0.0605 (9)−0.0138 (7)−0.0053 (7)0.0080 (7)
C100.0630 (9)0.0598 (9)0.0626 (9)−0.0092 (7)0.0081 (7)0.0016 (7)
C110.0571 (9)0.0582 (9)0.0687 (10)−0.0089 (7)0.0041 (7)−0.0073 (7)
C120.0677 (11)0.1012 (15)0.0823 (12)−0.0061 (10)0.0152 (9)−0.0173 (11)
C130.0573 (11)0.1235 (19)0.125 (2)0.0081 (11)0.0063 (12)−0.0504 (16)
C140.0822 (14)0.0752 (13)0.1122 (17)0.0145 (10)−0.0234 (12)−0.0352 (12)
C150.0834 (14)0.0780 (12)0.0816 (12)−0.0117 (10)−0.0150 (10)−0.0032 (10)
C160.0630 (10)0.0764 (11)0.0705 (10)−0.0161 (8)0.0004 (8)−0.0039 (8)
C170.050 (2)0.086 (3)0.079 (3)−0.0014 (19)0.0047 (18)0.002 (2)
C180.088 (4)0.084 (4)0.091 (3)0.033 (3)−0.011 (3)−0.017 (3)
C190.069 (3)0.087 (3)0.150 (8)−0.011 (2)−0.024 (4)−0.006 (4)
C1710.052 (2)0.082 (3)0.103 (4)−0.003 (2)0.020 (2)0.000 (3)
C1810.164 (10)0.089 (6)0.253 (16)−0.004 (6)−0.023 (9)0.054 (7)
C1910.100 (7)0.194 (13)0.133 (7)0.046 (7)−0.045 (5)−0.088 (8)
C200.0715 (12)0.0963 (14)0.0802 (12)0.0151 (10)−0.0134 (9)0.0089 (10)
C220.0577 (9)0.0707 (11)0.0840 (11)−0.0181 (8)−0.0025 (8)0.0016 (9)
C230.0835 (14)0.0758 (12)0.1151 (17)−0.0291 (10)−0.0043 (12)0.0166 (11)
O10.0531 (6)0.0561 (6)0.0748 (7)−0.0085 (4)−0.0115 (5)0.0130 (5)
O20.0812 (8)0.0705 (8)0.0798 (8)−0.0099 (6)0.0050 (6)0.0233 (6)
O30.0513 (6)0.0614 (6)0.0832 (8)−0.0095 (5)−0.0023 (5)0.0121 (5)
Geometric parameters (Å, º) top
C1—O11.3632 (17)C15—H150.9300
C1—C61.389 (2)C16—H160.9300
C1—C21.405 (2)C17—C181.499 (6)
C2—O31.3659 (18)C17—C191.540 (6)
C2—C31.381 (2)C17—H170.9800
C3—C41.397 (2)C18—H18A0.9600
C3—H30.9300C18—H18B0.9600
C4—C51.368 (2)C18—H18C0.9600
C4—C201.514 (2)C19—H19A0.9600
C5—C61.407 (2)C19—H19B0.9600
C5—H50.9300C19—H19C0.9600
C6—C71.477 (2)C171—C1811.536 (9)
C7—O21.2234 (19)C171—C1911.538 (8)
C7—C81.489 (2)C171—H1710.9800
C8—C101.342 (2)C181—H18D0.9600
C8—C91.501 (2)C181—H18E0.9600
C9—O11.4351 (18)C181—H18F0.9600
C9—H9A0.9700C191—H19D0.9600
C9—H9B0.9700C191—H19E0.9600
C10—C111.462 (2)C191—H19F0.9600
C10—H100.9300C20—H20A0.9600
C11—C161.392 (2)C20—H20B0.9600
C11—C121.396 (3)C20—H20C0.9600
C12—C131.375 (3)C22—O31.4294 (19)
C12—H120.9300C22—C231.489 (3)
C13—C141.379 (4)C22—H22A0.9700
C13—H130.9300C22—H22B0.9700
C14—C151.384 (3)C23—H23A0.9600
C14—C171.550 (5)C23—H23B0.9600
C14—C1711.568 (5)C23—H23C0.9600
C15—C161.375 (3)
O1—C1—C6123.15 (13)C19—C17—C14103.5 (5)
O1—C1—C2116.76 (13)C18—C17—H17111.5
C6—C1—C2120.07 (13)C19—C17—H17111.5
O3—C2—C3125.65 (14)C14—C17—H17111.5
O3—C2—C1115.38 (13)C17—C18—H18A109.5
C3—C2—C1118.96 (14)C17—C18—H18B109.5
C2—C3—C4121.87 (15)H18A—C18—H18B109.5
C2—C3—H3119.1C17—C18—H18C109.5
C4—C3—H3119.1H18A—C18—H18C109.5
C5—C4—C3118.40 (14)H18B—C18—H18C109.5
C5—C4—C20122.08 (17)C17—C19—H19A109.5
C3—C4—C20119.50 (16)C17—C19—H19B109.5
C4—C5—C6121.61 (15)H19A—C19—H19B109.5
C4—C5—H5119.2C17—C19—H19C109.5
C6—C5—H5119.2H19A—C19—H19C109.5
C1—C6—C5119.07 (14)H19B—C19—H19C109.5
C1—C6—C7119.98 (13)C181—C171—C191100.2 (12)
C5—C6—C7120.90 (14)C181—C171—C14105.3 (7)
O2—C7—C6121.86 (15)C191—C171—C14106.7 (6)
O2—C7—C8122.52 (15)C181—C171—H171114.4
C6—C7—C8115.61 (13)C191—C171—H171114.4
C10—C8—C7119.45 (14)C14—C171—H171114.4
C10—C8—C9124.88 (14)C171—C181—H18D109.5
C7—C8—C9115.66 (13)C171—C181—H18E109.5
O1—C9—C8113.53 (12)H18D—C181—H18E109.5
O1—C9—H9A108.9C171—C181—H18F109.5
C8—C9—H9A108.9H18D—C181—H18F109.5
O1—C9—H9B108.9H18E—C181—H18F109.5
C8—C9—H9B108.9C171—C191—H19D109.5
H9A—C9—H9B107.7C171—C191—H19E109.5
C8—C10—C11129.32 (15)H19D—C191—H19E109.5
C8—C10—H10115.3C171—C191—H19F109.5
C11—C10—H10115.3H19D—C191—H19F109.5
C16—C11—C12116.94 (17)H19E—C191—H19F109.5
C16—C11—C10123.74 (15)C4—C20—H20A109.5
C12—C11—C10119.30 (16)C4—C20—H20B109.5
C13—C12—C11121.0 (2)H20A—C20—H20B109.5
C13—C12—H12119.5C4—C20—H20C109.5
C11—C12—H12119.5H20A—C20—H20C109.5
C12—C13—C14122.1 (2)H20B—C20—H20C109.5
C12—C13—H13119.0O3—C22—C23107.23 (15)
C14—C13—H13119.0O3—C22—H22A110.3
C13—C14—C15116.85 (19)C23—C22—H22A110.3
C13—C14—C17133.8 (3)O3—C22—H22B110.3
C15—C14—C17109.3 (3)C23—C22—H22B110.3
C13—C14—C171105.8 (4)H22A—C22—H22B108.5
C15—C14—C171137.1 (4)C22—C23—H23A109.5
C16—C15—C14122.0 (2)C22—C23—H23B109.5
C16—C15—H15119.0H23A—C23—H23B109.5
C14—C15—H15119.0C22—C23—H23C109.5
C15—C16—C11121.08 (18)H23A—C23—H23C109.5
C15—C16—H16119.5H23B—C23—H23C109.5
C11—C16—H16119.5C1—O1—C9115.47 (12)
C18—C17—C19109.9 (8)C2—O3—C22117.71 (12)
C18—C17—C14108.7 (5)
O1—C1—C2—O3−1.1 (2)C16—C11—C12—C13−2.4 (3)
C6—C1—C2—O3−179.60 (13)C10—C11—C12—C13179.00 (19)
O1—C1—C2—C3179.92 (13)C11—C12—C13—C140.9 (3)
C6—C1—C2—C31.4 (2)C12—C13—C14—C150.7 (3)
O3—C2—C3—C4−179.43 (15)C12—C13—C14—C17−175.5 (3)
C1—C2—C3—C4−0.6 (2)C12—C13—C14—C171175.9 (3)
C2—C3—C4—C5−0.6 (2)C13—C14—C15—C16−0.7 (3)
C2—C3—C4—C20178.01 (16)C17—C14—C15—C16176.4 (2)
C3—C4—C5—C61.0 (3)C171—C14—C15—C16−173.9 (3)
C20—C4—C5—C6−177.59 (16)C14—C15—C16—C11−0.9 (3)
O1—C1—C6—C5−179.45 (14)C12—C11—C16—C152.5 (3)
C2—C1—C6—C5−1.1 (2)C10—C11—C16—C15−179.04 (17)
O1—C1—C6—C7−1.9 (2)C13—C14—C17—C1847.0 (8)
C2—C1—C6—C7176.48 (14)C15—C14—C17—C18−129.5 (6)
C4—C5—C6—C1−0.2 (2)C171—C14—C17—C1864.2 (8)
C4—C5—C6—C7−177.71 (15)C13—C14—C17—C19−69.9 (7)
C1—C6—C7—O2−172.15 (15)C15—C14—C17—C19113.7 (7)
C5—C6—C7—O25.3 (3)C171—C14—C17—C19−52.7 (8)
C1—C6—C7—C87.1 (2)C13—C14—C171—C181111.4 (9)
C5—C6—C7—C8−175.42 (14)C15—C14—C171—C181−74.9 (9)
O2—C7—C8—C1014.1 (2)C17—C14—C171—C181−55.8 (9)
C6—C7—C8—C10−165.17 (15)C13—C14—C171—C191−142.7 (9)
O2—C7—C8—C9−166.14 (16)C15—C14—C171—C19131.0 (10)
C6—C7—C8—C914.6 (2)C17—C14—C171—C19150.1 (9)
C10—C8—C9—O1138.48 (17)C6—C1—O1—C9−26.1 (2)
C7—C8—C9—O1−41.3 (2)C2—C1—O1—C9155.44 (14)
C7—C8—C10—C11179.85 (15)C8—C9—O1—C147.03 (19)
C9—C8—C10—C110.1 (3)C3—C2—O3—C229.9 (2)
C8—C10—C11—C1633.2 (3)C1—C2—O3—C22−168.97 (14)
C8—C10—C11—C12−148.30 (19)C23—C22—O3—C2177.70 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O2i0.972.603.407 (2)141
C10—H10···O20.932.472.823 (2)103
Symmetry code: (i) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formulaC22H24O3
Mr336.41
Crystal system, space groupMonoclinic, P21/n
Temperature (K)295
a, b, c (Å)10.3568 (9), 16.8154 (15), 10.8962 (10)
β (°) 99.873 (1)
V (Å3)1869.5 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.22 × 0.18 × 0.16
Data collection
DiffractometerBruker SMART APEX area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.983, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections		21105, 4385, 3220
Rint0.026
(sin θ/λ)max (Å−1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.158, 1.02
No. of reflections4385
No. of parameters256
No. of restraints4
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.23, −0.14

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top
C1—O11.3632 (17)C9—O11.4351 (18)
C2—O31.3659 (18)C22—O31.4294 (19)
C7—O21.2234 (19)
O1—C1—C6123.15 (13)O2—C7—C8122.52 (15)
O1—C1—C2116.76 (13)O1—C9—C8113.53 (12)
O3—C2—C3125.65 (14)O3—C22—C23107.23 (15)
O3—C2—C1115.38 (13)C1—O1—C9115.47 (12)
O2—C7—C6121.86 (15)C2—O3—C22117.71 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O2i0.972.603.407 (2)141
C10—H10···O20.932.472.823 (2)103
Symmetry code: (i) −x+2, −y, −z+2.
 

References

First citationBruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationKang, J. G., Shin, S. Y., Kim, M. J., Bajpai, V., Maheshwari, D. K. & Kang, S. C. (2004). J. Antibiot. 57, 726–731.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationMarx, A., Manivannan, V., Suresh, R., Kanagam, C. C. & Büyükgüngör, O. (2007). Acta Cryst. E63, o4383.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationNissa, M. N., Rajakannan, V., Kim, M.-J. & Velmurugan, D. (2001). Acta Cryst. E57, o1230–o1232.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationPuviarasan, K., Govindasamy, L., Velmurugan, D., Shanmuga Sundara Raj, S., Shanmuga Sundaram, M., Raghunathan, R. & Fun, H.-K. (1998). Acta Cryst. C54, 961–963.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationSchollmeyer, D., Kammerer, B., Peifer, C. & Laufer, S. (2005). Acta Cryst. E61, o868–o869.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationTillekeratne, L. M., Sherette, A., Grossman, P., Hupe, L., Hupe, D. & Hudson, R. A. (2001). Bioorg. Med. Chem. Lett. 11, 2763–2764.  Web of Science CrossRef PubMed CAS 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.

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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o328
https://doi.org/10.1107/S1600536807066925
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