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The title compound, C23H24O5, a bis­(3,4-dimethoxy­phen­yl)­cyclo­penta­none derivative related to curcumin, shows noncrystallographic C2v symmetry with two noncrystallographic mirror planes inter­secting the cyclo­penta­none ring, resulting in a noncrystallographic twofold axis along the C=O double bond. The mol­ecule is basically planar, the angles between the planes of the cyclo­penta­none ring and those of the two benzene rings being 2.5 (3) and 1.2 (7)°. The dihedral angles of both meth­oxy groups with the benzene rings are nearly identical [179.05 (11), 177.88 (11), −172.51 (12) and 176.11 (13)°]. The two 3,4-dimethoxy­phenyl groups also lie within the plane of the mol­ecule and the angle between them is 1.4 (1)°. The crystal packing is stabilized by inter­molecular C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029339/zl2029sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029339/zl2029Isup2.hkl
Contains datablock I

CCDC reference: 655004

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.047
  • wR factor = 0.128
  • Data-to-parameter ratio = 21.1

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Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.861 1.000 Tmin(prime) and Tmax expected: 0.954 0.976 RR(prime) = 0.880 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 20
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: ...Each of the authors listed made significant contributions to this paper. Thank you for your consideration.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Comment top

The title compound, (I), 2,5-bis(3,4-dimethoxyphenyl)cyclopentanone, (synthesis; Fig. 3) is a biologically active compound. Derivatives of dibenzylidene acetone, cyclopentanone and cyclohexanone exhibit potent anti-inflammatory, antibacterial and antioxidation activity. Closely realted to the title compound is curcumin, (1,7-bis(4-hydroxy-3-methoxy-phenyl)hepta-1,6-diene-3,5-dione), which is the main constituent of turmeric, the commonly used spice. It has been widely used as an anti-inflammatory, antibacterial, antioxidant, antihepatotoxic, hypocholesterolanemia, anti-cyclooxygenase, anti-cancer and radical scavenger agent. It is reported that curcumin is nontoxic in high doses and substitution on the aromatic rings with electron donating and withdrawing groups increases anti-inflammatory activity (Reksohadiprodjo et al., 2004). Certain curcumin analogs are described to be potent aldose reductase inhibitors (Du et al., 2006).

Hydrogen-bonding interactions in 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione have been reported (Girija et al., 2004), and related crystal and molecular structural studies of 2-(p-methylbenzyl)cyclopentanone and 2-(p-chlorobenzyl)-5-(p-bromobenzylidene)cyclopentanone (Theocharis et al., 1982) as well as one of the photodimerizable compound 5-benzylidene-2-(p-chlorobenzyl)cyclopentanone (Theocharis et al., 1981) and 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one (Butcher et al., 2006) have been reported. In view of the importance of these dibenzylidene derivatives, the present paper reports the crystal structure of the title compound, (I), C23H24O5.

Related literature top

For the synthesis of the title compouund, see: Furniss et al. (1989). For biological activity of the title compound and curcumin, see: Du et al. (2006) and Reksohadiprodjo et al. (2004), respectively. For related structures, see: Girija et al. (2004); Theocharis et al. (1981, 1982); Butcher et al. (2006).

Experimental top

The title compound was synthesized according to the method reported in the literature (Furniss et al., 1989). A solution of 25 g of NaOH in 250 ml of water and 200 ml of ethanol was placed in a 500 ml bolt head flask provided with a mechanical stirrer. The flask was immersed in a water bath and the temperature of the solution was maintained at 393–398 K. The solution was stirred vigorously and added to one half of a previously prepared mixture of 3,4-dimethoxybenzaldehyde (41.5 g, 0.25 mol) and cyclopentanone (10.5 g, 0.125 mol). A flocculent precipitate is formed within 5–10 minutes. After 25 minutes, the remainder of the aldehyde-cyclopentanone mixture was added and the stirring was continued for additional 45 minutes. The crude product obtained was filtered and washed with cold water to eliminate the NaOH as completely as possible. The compound was purified by crystallization from ethanol (yield: 65%). Single crystal were grown in a acetone-toluene mixture (2:8) by slow evaporation (m.p.: 398–403 K). Analysis for C23H24O5: Found (Calculated): C:72.55 (72.61); H: 6.29% (6.36%).

Refinement top

The H atoms were included in the riding model approximation with C—H = 0.95–0.99 Å, and with Uiso(H) = 1.18–1.52Ueq(C).

Structure description top

The title compound, (I), 2,5-bis(3,4-dimethoxyphenyl)cyclopentanone, (synthesis; Fig. 3) is a biologically active compound. Derivatives of dibenzylidene acetone, cyclopentanone and cyclohexanone exhibit potent anti-inflammatory, antibacterial and antioxidation activity. Closely realted to the title compound is curcumin, (1,7-bis(4-hydroxy-3-methoxy-phenyl)hepta-1,6-diene-3,5-dione), which is the main constituent of turmeric, the commonly used spice. It has been widely used as an anti-inflammatory, antibacterial, antioxidant, antihepatotoxic, hypocholesterolanemia, anti-cyclooxygenase, anti-cancer and radical scavenger agent. It is reported that curcumin is nontoxic in high doses and substitution on the aromatic rings with electron donating and withdrawing groups increases anti-inflammatory activity (Reksohadiprodjo et al., 2004). Certain curcumin analogs are described to be potent aldose reductase inhibitors (Du et al., 2006).

Hydrogen-bonding interactions in 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione have been reported (Girija et al., 2004), and related crystal and molecular structural studies of 2-(p-methylbenzyl)cyclopentanone and 2-(p-chlorobenzyl)-5-(p-bromobenzylidene)cyclopentanone (Theocharis et al., 1982) as well as one of the photodimerizable compound 5-benzylidene-2-(p-chlorobenzyl)cyclopentanone (Theocharis et al., 1981) and 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one (Butcher et al., 2006) have been reported. In view of the importance of these dibenzylidene derivatives, the present paper reports the crystal structure of the title compound, (I), C23H24O5.

For the synthesis of the title compouund, see: Furniss et al. (1989). For biological activity of the title compound and curcumin, see: Du et al. (2006) and Reksohadiprodjo et al. (2004), respectively. For related structures, see: Girija et al. (2004); Theocharis et al. (1981, 1982); Butcher et al. (2006).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. Molecular structure of C23H24O5, (I), showing the atom labeling and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of C23H24O5 viewed down the a axis. Dashed lines indicate C—H···O hydrogen bonds.
[Figure 3] Fig. 3. Synthesis scheme of C23H24O5.
2,5-Bis(3,4-dimethoxybenzylidene)cyclopentanone top
Crystal data top
C23H24O5F(000) = 808
Mr = 380.42Dx = 1.303 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.9492 (9) ÅCell parameters from 6322 reflections
b = 8.8428 (10) Åθ = 2.7–29.5°
c = 27.603 (3) ŵ = 0.09 mm1
β = 92.421 (2)°T = 173 K
V = 1938.6 (4) Å3Plate, colorless
Z = 40.50 × 0.48 × 0.27 mm
Data collection top
Bruker APEX II CCD area-detector
diffractometer
5434 independent reflections
Radiation source: fine-focus sealed tube4383 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 30.1°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1010
Tmin = 0.861, Tmax = 1.000k = 912
21225 measured reflectionsl = 3737
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0653P)2 + 0.4601P]
where P = (Fo2 + 2Fc2)/3
5434 reflections(Δ/σ)max = 0.001
257 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C23H24O5V = 1938.6 (4) Å3
Mr = 380.42Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.9492 (9) ŵ = 0.09 mm1
b = 8.8428 (10) ÅT = 173 K
c = 27.603 (3) Å0.50 × 0.48 × 0.27 mm
β = 92.421 (2)°
Data collection top
Bruker APEX II CCD area-detector
diffractometer
5434 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
4383 reflections with I > 2σ(I)
Tmin = 0.861, Tmax = 1.000Rint = 0.025
21225 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.02Δρmax = 0.35 e Å3
5434 reflectionsΔρmin = 0.23 e Å3
257 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
O10.81476 (12)0.25378 (12)0.56791 (4)0.0441 (3)
O1A0.63787 (11)0.20756 (11)0.30071 (3)0.0363 (2)
O2A0.38946 (10)0.05138 (11)0.32971 (3)0.0360 (2)
O1B0.11569 (11)0.80398 (12)0.71096 (3)0.0394 (2)
O2B0.00659 (11)0.69043 (12)0.62888 (4)0.0416 (2)
C10.67617 (15)0.27066 (14)0.54724 (4)0.0292 (2)
C20.62053 (14)0.20262 (13)0.50019 (4)0.0264 (2)
C30.44328 (14)0.25268 (13)0.48725 (4)0.0263 (2)
H3A0.36770.16400.48360.032*
H3B0.43940.30960.45630.032*
C40.38814 (14)0.35517 (14)0.52927 (4)0.0264 (2)
H4A0.35770.45720.51700.032*
H4B0.28940.31120.54480.032*
C50.53647 (14)0.36409 (13)0.56496 (4)0.0264 (2)
C1A0.72554 (14)0.11349 (14)0.47582 (4)0.0289 (2)
H1AA0.83380.10060.49120.035*
C2A0.70094 (14)0.03375 (13)0.42997 (4)0.0261 (2)
C3A0.83432 (14)0.05166 (14)0.41327 (4)0.0300 (2)
H3AA0.93810.05370.43160.036*
C4A0.81865 (14)0.13364 (15)0.37044 (4)0.0305 (3)
H4AA0.91100.19130.35990.037*
C5A0.66858 (14)0.13152 (14)0.34312 (4)0.0282 (2)
C6A0.53173 (13)0.04561 (14)0.35913 (4)0.0270 (2)
C7A0.54844 (14)0.03504 (13)0.40180 (4)0.0269 (2)
H7AA0.45590.09240.41240.032*
C8A0.77269 (18)0.29440 (18)0.28243 (5)0.0421 (3)
H8AA0.73330.34760.25290.063*
H8AB0.81140.36820.30690.063*
H8AC0.86590.22700.27490.063*
C9A0.24621 (15)0.02963 (17)0.34540 (5)0.0369 (3)
H9AA0.15190.01580.32180.055*
H9AB0.27360.13740.34810.055*
H9AC0.21480.00880.37710.055*
C1B0.55581 (14)0.43827 (14)0.60739 (4)0.0287 (2)
H1BA0.66260.42510.62360.034*
C2B0.44034 (14)0.53533 (14)0.63258 (4)0.0270 (2)
C3B0.49604 (15)0.59992 (15)0.67642 (4)0.0321 (3)
H3BA0.60860.58250.68800.039*
C4B0.39165 (16)0.68903 (15)0.70360 (4)0.0332 (3)
H4BA0.43240.72990.73370.040*
C5B0.22851 (15)0.71848 (14)0.68699 (4)0.0301 (2)
C6B0.16958 (14)0.65609 (14)0.64237 (4)0.0291 (2)
C7B0.27334 (14)0.56639 (14)0.61594 (4)0.0278 (2)
H7BA0.23210.52470.58600.033*
C8B0.18210 (19)0.88207 (18)0.75296 (5)0.0444 (3)
H8BA0.09560.94910.76530.067*
H8BB0.28000.94210.74430.067*
H8BC0.21620.80850.77800.067*
C9B0.05314 (17)0.6372 (2)0.58261 (6)0.0497 (4)
H9BA0.16840.67330.57600.075*
H9BB0.05190.52640.58240.075*
H9BC0.01980.67540.55760.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0382 (5)0.0514 (6)0.0414 (5)0.0209 (4)0.0143 (4)0.0106 (5)
O1A0.0337 (4)0.0433 (6)0.0320 (4)0.0100 (4)0.0021 (3)0.0113 (4)
O2A0.0249 (4)0.0460 (6)0.0366 (5)0.0072 (4)0.0038 (3)0.0109 (4)
O1B0.0330 (4)0.0439 (6)0.0415 (5)0.0023 (4)0.0055 (4)0.0180 (4)
O2B0.0237 (4)0.0534 (6)0.0471 (5)0.0050 (4)0.0058 (4)0.0182 (5)
C10.0311 (5)0.0274 (6)0.0287 (5)0.0075 (4)0.0035 (4)0.0006 (4)
C20.0289 (5)0.0232 (5)0.0268 (5)0.0038 (4)0.0018 (4)0.0024 (4)
C30.0252 (5)0.0264 (6)0.0272 (5)0.0014 (4)0.0003 (4)0.0008 (4)
C40.0244 (5)0.0271 (6)0.0277 (5)0.0012 (4)0.0002 (4)0.0009 (4)
C50.0275 (5)0.0246 (6)0.0269 (5)0.0039 (4)0.0015 (4)0.0034 (4)
C1A0.0271 (5)0.0287 (6)0.0304 (6)0.0039 (4)0.0031 (4)0.0012 (5)
C2A0.0251 (5)0.0243 (6)0.0290 (5)0.0032 (4)0.0014 (4)0.0018 (4)
C3A0.0240 (5)0.0324 (6)0.0336 (6)0.0043 (4)0.0004 (4)0.0009 (5)
C4A0.0253 (5)0.0336 (6)0.0330 (6)0.0063 (4)0.0055 (4)0.0005 (5)
C5A0.0284 (5)0.0291 (6)0.0276 (5)0.0017 (4)0.0043 (4)0.0020 (4)
C6A0.0221 (5)0.0288 (6)0.0300 (5)0.0015 (4)0.0003 (4)0.0002 (4)
C7A0.0234 (5)0.0274 (6)0.0301 (5)0.0042 (4)0.0035 (4)0.0013 (4)
C8A0.0437 (7)0.0458 (8)0.0373 (7)0.0151 (6)0.0081 (6)0.0077 (6)
C9A0.0234 (5)0.0486 (8)0.0386 (7)0.0070 (5)0.0001 (5)0.0015 (6)
C1B0.0287 (5)0.0302 (6)0.0267 (5)0.0056 (4)0.0050 (4)0.0023 (4)
C2B0.0278 (5)0.0287 (6)0.0242 (5)0.0025 (4)0.0028 (4)0.0012 (4)
C3B0.0305 (6)0.0374 (7)0.0276 (5)0.0040 (5)0.0078 (4)0.0016 (5)
C4B0.0364 (6)0.0373 (7)0.0255 (5)0.0013 (5)0.0052 (5)0.0060 (5)
C5B0.0303 (5)0.0296 (6)0.0305 (6)0.0031 (5)0.0027 (4)0.0054 (5)
C6B0.0231 (5)0.0319 (6)0.0322 (6)0.0016 (4)0.0019 (4)0.0034 (5)
C7B0.0271 (5)0.0303 (6)0.0257 (5)0.0008 (4)0.0027 (4)0.0036 (4)
C8B0.0472 (8)0.0455 (8)0.0413 (7)0.0106 (6)0.0103 (6)0.0193 (6)
C9B0.0262 (6)0.0704 (11)0.0513 (8)0.0032 (6)0.0120 (6)0.0175 (8)
Geometric parameters (Å, º) top
O1—C11.2282 (14)C4A—H4AA0.9500
O1A—C5A1.3631 (14)C5A—C6A1.4129 (15)
O1A—C8A1.4278 (15)C6A—C7A1.3787 (16)
O2A—C6A1.3652 (14)C7A—H7AA0.9500
O2A—C9A1.4280 (14)C8A—H8AA0.9800
O1B—C5B1.3652 (15)C8A—H8AB0.9800
O1B—C8B1.4310 (16)C8A—H8AC0.9800
O2B—C6B1.3671 (14)C9A—H9AA0.9800
O2B—C9B1.4236 (17)C9A—H9AB0.9800
C1—C21.4819 (16)C9A—H9AC0.9800
C1—C51.4836 (16)C1B—C2B1.4548 (16)
C2—C1A1.3483 (16)C1B—H1BA0.9500
C2—C31.5054 (15)C2B—C3B1.3933 (16)
C3—C41.5498 (16)C2B—C7B1.4133 (15)
C3—H3A0.9900C3B—C4B1.3876 (18)
C3—H3B0.9900C3B—H3BA0.9500
C4—C51.5064 (15)C4B—C5B1.3819 (17)
C4—H4A0.9900C4B—H4BA0.9500
C4—H4B0.9900C5B—C6B1.4114 (16)
C5—C1B1.3454 (16)C6B—C7B1.3758 (17)
C1A—C2A1.4546 (16)C7B—H7BA0.9500
C1A—H1AA0.9500C8B—H8BA0.9800
C2A—C3A1.3959 (16)C8B—H8BB0.9800
C2A—C7A1.4123 (15)C8B—H8BC0.9800
C3A—C4A1.3881 (17)C9B—H9BA0.9800
C3A—H3AA0.9500C9B—H9BB0.9800
C4A—C5A1.3842 (16)C9B—H9BC0.9800
C5A—O1A—C8A117.32 (10)O1A—C8A—H8AA109.5
C6A—O2A—C9A116.87 (9)O1A—C8A—H8AB109.5
C5B—O1B—C8B115.62 (10)H8AA—C8A—H8AB109.5
C6B—O2B—C9B116.58 (10)O1A—C8A—H8AC109.5
O1—C1—C2125.91 (11)H8AA—C8A—H8AC109.5
O1—C1—C5125.71 (11)H8AB—C8A—H8AC109.5
C2—C1—C5108.38 (9)O2A—C9A—H9AA109.5
C1A—C2—C1120.43 (10)O2A—C9A—H9AB109.5
C1A—C2—C3130.28 (11)H9AA—C9A—H9AB109.5
C1—C2—C3109.29 (9)O2A—C9A—H9AC109.5
C2—C3—C4106.61 (9)H9AA—C9A—H9AC109.5
C2—C3—H3A110.4H9AB—C9A—H9AC109.5
C4—C3—H3A110.4C5—C1B—C2B130.72 (10)
C2—C3—H3B110.4C5—C1B—H1BA114.6
C4—C3—H3B110.4C2B—C1B—H1BA114.6
H3A—C3—H3B108.6C3B—C2B—C7B117.53 (10)
C5—C4—C3106.37 (9)C3B—C2B—C1B118.24 (10)
C5—C4—H4A110.5C7B—C2B—C1B124.22 (10)
C3—C4—H4A110.5C4B—C3B—C2B121.82 (11)
C5—C4—H4B110.5C4B—C3B—H3BA119.1
C3—C4—H4B110.5C2B—C3B—H3BA119.1
H4A—C4—H4B108.6C5B—C4B—C3B120.12 (11)
C1B—C5—C1119.93 (10)C5B—C4B—H4BA119.9
C1B—C5—C4130.72 (10)C3B—C4B—H4BA119.9
C1—C5—C4109.34 (10)O1B—C5B—C4B124.75 (11)
C2—C1A—C2A130.85 (11)O1B—C5B—C6B116.03 (11)
C2—C1A—H1AA114.6C4B—C5B—C6B119.22 (11)
C2A—C1A—H1AA114.6O2B—C6B—C7B124.47 (11)
C3A—C2A—C7A117.96 (10)O2B—C6B—C5B115.27 (10)
C3A—C2A—C1A118.26 (10)C7B—C6B—C5B120.26 (10)
C7A—C2A—C1A123.76 (10)C6B—C7B—C2B121.04 (10)
C4A—C3A—C2A121.45 (11)C6B—C7B—H7BA119.5
C4A—C3A—H3AA119.3C2B—C7B—H7BA119.5
C2A—C3A—H3AA119.3O1B—C8B—H8BA109.5
C5A—C4A—C3A120.08 (10)O1B—C8B—H8BB109.5
C5A—C4A—H4AA120.0H8BA—C8B—H8BB109.5
C3A—C4A—H4AA120.0O1B—C8B—H8BC109.5
O1A—C5A—C4A125.46 (10)H8BA—C8B—H8BC109.5
O1A—C5A—C6A114.93 (10)H8BB—C8B—H8BC109.5
C4A—C5A—C6A119.61 (11)O2B—C9B—H9BA109.5
O2A—C6A—C7A125.11 (10)O2B—C9B—H9BB109.5
O2A—C6A—C5A115.04 (10)H9BA—C9B—H9BB109.5
C7A—C6A—C5A119.85 (10)O2B—C9B—H9BC109.5
C6A—C7A—C2A121.04 (10)H9BA—C9B—H9BC109.5
C6A—C7A—H7AA119.5H9BB—C9B—H9BC109.5
C2A—C7A—H7AA119.5
O1—C1—C2—C1A0.3 (2)O1A—C5A—C6A—C7A179.55 (11)
C5—C1—C2—C1A179.10 (11)C4A—C5A—C6A—C7A0.16 (18)
O1—C1—C2—C3179.31 (13)O2A—C6A—C7A—C2A179.80 (11)
C5—C1—C2—C30.12 (13)C5A—C6A—C7A—C2A0.17 (18)
C1A—C2—C3—C4179.60 (12)C3A—C2A—C7A—C6A0.02 (17)
C1—C2—C3—C40.75 (13)C1A—C2A—C7A—C6A178.56 (11)
C2—C3—C4—C51.09 (12)C1—C5—C1B—C2B179.78 (12)
O1—C1—C5—C1B0.6 (2)C4—C5—C1B—C2B0.6 (2)
C2—C1—C5—C1B179.94 (11)C5—C1B—C2B—C3B179.06 (13)
O1—C1—C5—C4179.98 (13)C5—C1B—C2B—C7B2.2 (2)
C2—C1—C5—C40.59 (13)C7B—C2B—C3B—C4B1.34 (19)
C3—C4—C5—C1B179.71 (12)C1B—C2B—C3B—C4B177.47 (12)
C3—C4—C5—C11.04 (13)C2B—C3B—C4B—C5B1.3 (2)
C1—C2—C1A—C2A179.44 (12)C8B—O1B—C5B—C4B8.17 (19)
C3—C2—C1A—C2A1.8 (2)C8B—O1B—C5B—C6B172.51 (12)
C2—C1A—C2A—C3A179.99 (13)C3B—C4B—C5B—O1B179.72 (12)
C2—C1A—C2A—C7A1.4 (2)C3B—C4B—C5B—C6B0.4 (2)
C7A—C2A—C3A—C4A0.23 (18)C9B—O2B—C6B—C7B4.6 (2)
C1A—C2A—C3A—C4A178.44 (11)C9B—O2B—C6B—C5B176.11 (13)
C2A—C3A—C4A—C5A0.24 (19)O1B—C5B—C6B—O2B0.33 (17)
C8A—O1A—C5A—C4A1.26 (19)C4B—C5B—C6B—O2B179.69 (12)
C8A—O1A—C5A—C6A179.05 (11)O1B—C5B—C6B—C7B179.01 (11)
C3A—C4A—C5A—O1A179.72 (12)C4B—C5B—C6B—C7B0.35 (19)
C3A—C4A—C5A—C6A0.04 (18)O2B—C6B—C7B—C2B179.56 (12)
C9A—O2A—C6A—C7A1.76 (18)C5B—C6B—C7B—C2B0.28 (19)
C9A—O2A—C6A—C5A177.88 (11)C3B—C2B—C7B—C6B0.54 (18)
O1A—C5A—C6A—O2A0.11 (16)C1B—C2B—C7B—C6B178.18 (12)
C4A—C5A—C6A—O2A179.82 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4B—H4BA···O1Ai0.952.423.2556 (15)146
Symmetry code: (i) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC23H24O5
Mr380.42
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)7.9492 (9), 8.8428 (10), 27.603 (3)
β (°) 92.421 (2)
V3)1938.6 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.50 × 0.48 × 0.27
Data collection
DiffractometerBruker APEX II CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.861, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
21225, 5434, 4383
Rint0.025
(sin θ/λ)max1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.128, 1.02
No. of reflections5434
No. of parameters257
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.23

Computer programs: APEX2 (Bruker, 2006), APEX2, SHELXS90 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXTL (Bruker, 2000).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4B—H4BA···O1Ai0.952.423.2556 (15)146.1
Symmetry code: (i) x, y+1/2, z+1/2.
 

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