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The title compound, C21H22O5, a derivative of the anti­oxidant, anti-inflammatory compound curcumin, crystallizes with two mol­ecules (A and B) in the asymmetric unit. The mean planes of the two 3,4-dimethoxy­phenyl groups in A and B make dihedral angles of 57.9 (7) and 33.4 (3)°. An extensive network of inter­molecular C—H...O hydrogen bonds stabilizes the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026888/cv2246sup1.cif
Contains datablocks hsy86mom, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026888/cv2246Isup2.hkl
Contains datablock I

CCDC reference: 654883

Key indicators

  • Single-crystal X-ray study
  • T = 103 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.041
  • wR factor = 0.114
  • Data-to-parameter ratio = 21.3

checkCIF/PLATON results

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Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 20
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Comment top

The title compound, C21H22O5, 1,5-bis(3,4-dimethoxyphenyl) penta-1,4-dien-3-one, (I), is a biologically active compound. Derivatives of dibenzylidene acetone, cyclopentanone and cyclohexanone exhibit potent anti-inflammatory, antibacterial and antioxidation activity. Closely related 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 at high doses and substitution on the aromatic rings with electron donating and withdrawing groups increases anti-inflammatory activity (Reksohadiprodjo et al., 2004).

Hydrogen-bonding interactions in 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione have been reported (Girija et al., 2004) as well as related crystal and molecular structural studies of 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one (Butcher et al., 2006). In view of the importance of these dibenzylidene derivatives, the present paper reports the crystal structure of the title compound C21H22O5.

Related literature top

For biological activity of the title compound and curcumin, see: Reksohadiprodjo et al. (2004). For hydrogen-bonding interactions and related structures, see: Girija et al. (2004) and Butcher et al. (2006). For related literature, see: Author? (1989).

Experimental top

The title compound was synthesized with a yield of 75% according to the method reported in Author? (1989). The compound was purified by recrystallization from ethanol. The crystal was grown in acetone:toluene [50:50] solvent by the slow evaporation technique (m.p.:368–373 K). Analysis for C21H22O5: Found (Calculated): C: 71.20 (71.17%); H: 6.18 (6.22%).

Refinement top

The H atoms were included in calculated positions (C—H 0.95–0.98 Å) and refined in riding model approximation, with Uiso(H) = 1.2–1.5Ueq(C).

Structure description top

The title compound, C21H22O5, 1,5-bis(3,4-dimethoxyphenyl) penta-1,4-dien-3-one, (I), is a biologically active compound. Derivatives of dibenzylidene acetone, cyclopentanone and cyclohexanone exhibit potent anti-inflammatory, antibacterial and antioxidation activity. Closely related 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 at high doses and substitution on the aromatic rings with electron donating and withdrawing groups increases anti-inflammatory activity (Reksohadiprodjo et al., 2004).

Hydrogen-bonding interactions in 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione have been reported (Girija et al., 2004) as well as related crystal and molecular structural studies of 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one (Butcher et al., 2006). In view of the importance of these dibenzylidene derivatives, the present paper reports the crystal structure of the title compound C21H22O5.

For biological activity of the title compound and curcumin, see: Reksohadiprodjo et al. (2004). For hydrogen-bonding interactions and related structures, see: Girija et al. (2004) and Butcher et al. (2006). For related literature, see: Author? (1989).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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 (I), showing atomic labeling and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of (I), viewed down the b axis. Dashed lines indicate C—H···O hydrogen bonds.
1,5-Bis(3,4-dimethoxyphenyl)penta-1,4-dien-3-one top
Crystal data top
C21H22O5F(000) = 1504
Mr = 354.39Dx = 1.297 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 19.1646 (13) ÅCell parameters from 7695 reflections
b = 7.7488 (5) Åθ = 2.8–29.6°
c = 24.8495 (17) ŵ = 0.09 mm1
β = 100.414 (1)°T = 103 K
V = 3629.4 (4) Å3Prism, colourless
Z = 80.56 × 0.35 × 0.24 mm
Data collection top
CCD area-detector
diffractometer
10146 independent reflections
Radiation source: fine-focus sealed tube8569 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 29.7°, θmin = 1.7°
Absorption correction: multi-scan
DENZO/SCALEPACK (Otwinowski & Minor, 1997)
h = 2626
Tmin = 0.950, Tmax = 0.988k = 1010
40342 measured reflectionsl = 3334
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0612P)2 + 0.9436P]
where P = (Fo2 + 2Fc2)/3
10146 reflections(Δ/σ)max = 0.002
477 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C21H22O5V = 3629.4 (4) Å3
Mr = 354.39Z = 8
Monoclinic, P21/cMo Kα radiation
a = 19.1646 (13) ŵ = 0.09 mm1
b = 7.7488 (5) ÅT = 103 K
c = 24.8495 (17) Å0.56 × 0.35 × 0.24 mm
β = 100.414 (1)°
Data collection top
CCD area-detector
diffractometer
10146 independent reflections
Absorption correction: multi-scan
DENZO/SCALEPACK (Otwinowski & Minor, 1997)
8569 reflections with I > 2σ(I)
Tmin = 0.950, Tmax = 0.988Rint = 0.027
40342 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 1.03Δρmax = 0.34 e Å3
10146 reflectionsΔρmin = 0.29 e Å3
477 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
O1A0.70296 (4)0.41530 (11)0.25313 (3)0.02419 (17)
O2A0.70709 (4)0.51375 (11)0.35211 (3)0.02445 (17)
O3A0.35878 (4)0.45882 (11)0.07001 (3)0.02442 (17)
O4A0.07684 (4)0.86400 (10)0.20454 (3)0.02421 (17)
O5A0.02272 (4)0.63640 (10)0.18184 (3)0.02352 (16)
O1B0.96885 (4)0.17449 (11)0.03878 (3)0.02650 (17)
O2B0.93567 (4)0.07348 (11)0.13096 (3)0.02318 (16)
O3B0.55536 (4)0.26262 (11)0.10438 (3)0.02574 (17)
O4B0.22391 (4)0.28208 (11)0.09563 (3)0.02277 (16)
O5B0.23280 (4)0.19771 (11)0.19409 (3)0.02292 (16)
C1A0.51544 (5)0.55102 (12)0.24296 (4)0.01736 (18)
C2A0.57740 (5)0.48719 (13)0.22675 (4)0.01750 (18)
H2AA0.57610.45180.19000.021*
C3A0.63995 (5)0.47606 (13)0.26423 (4)0.01795 (19)
C4A0.64228 (5)0.52836 (13)0.31906 (4)0.01887 (19)
C5A0.58134 (6)0.58896 (13)0.33525 (4)0.0203 (2)
H5AA0.58240.62280.37210.024*
C6A0.51839 (5)0.60011 (13)0.29714 (4)0.01938 (19)
H6AA0.47670.64200.30840.023*
C7A0.70226 (6)0.35031 (15)0.19927 (4)0.0241 (2)
H7AA0.74990.31010.19620.036*
H7AB0.68770.44220.17250.036*
H7AC0.66870.25400.19210.036*
C8A0.70952 (7)0.54299 (16)0.40909 (5)0.0300 (3)
H8AA0.75800.52490.42890.045*
H8AB0.67740.46240.42280.045*
H8AC0.69480.66180.41480.045*
C9A0.44789 (5)0.56426 (13)0.20514 (4)0.01823 (19)
H9AA0.40860.60590.21980.022*
C10A0.43560 (5)0.52354 (13)0.15173 (4)0.01880 (19)
H10A0.47530.49580.13540.023*
C11A0.36532 (5)0.51882 (13)0.11681 (4)0.01848 (19)
C12A0.30154 (5)0.57637 (13)0.13791 (4)0.01858 (19)
H12A0.30560.65930.16650.022*
C13A0.23810 (5)0.50987 (13)0.11618 (4)0.01900 (19)
H13A0.23750.42990.08710.023*
C14A0.16988 (5)0.54584 (13)0.13193 (4)0.01782 (19)
C15A0.15812 (5)0.69605 (13)0.16107 (4)0.01781 (19)
H15A0.19480.77940.16980.021*
C16A0.09345 (5)0.72227 (13)0.17689 (4)0.01791 (19)
C17A0.03876 (5)0.59741 (13)0.16468 (4)0.01875 (19)
C18A0.05038 (5)0.44979 (14)0.13599 (4)0.0204 (2)
H18A0.01430.36490.12790.024*
C19A0.11532 (5)0.42641 (14)0.11907 (4)0.0204 (2)
H19A0.12240.32690.09840.025*
C20A0.11770 (6)1.01596 (15)0.20083 (6)0.0313 (3)
H20A0.09511.11440.21560.047*
H20B0.12041.03800.16240.047*
H20C0.16560.99990.22190.047*
C21A0.08162 (6)0.52357 (15)0.16435 (5)0.0269 (2)
H21A0.12460.57410.17390.040*
H21B0.07230.41150.18250.040*
H21C0.08820.50790.12460.040*
C1B0.75664 (5)0.19846 (13)0.05722 (4)0.01803 (19)
C2B0.77562 (6)0.25613 (14)0.00882 (4)0.0209 (2)
H2BA0.74030.30140.01940.025*
C3B0.84584 (6)0.24834 (14)0.00126 (4)0.0225 (2)
H3BA0.85770.28640.03230.027*
C4B0.89870 (5)0.18555 (14)0.04228 (4)0.0205 (2)
C5B0.88064 (5)0.12898 (13)0.09200 (4)0.01874 (19)
C6B0.81052 (5)0.13416 (13)0.09856 (4)0.01809 (19)
H6BA0.79840.09340.13170.022*
C7B0.98831 (7)0.22779 (19)0.01151 (5)0.0341 (3)
H7BA1.03950.21290.00930.051*
H7BB0.97590.34960.01820.051*
H7BC0.96290.15750.04160.051*
C8B0.91785 (6)0.02067 (15)0.18211 (4)0.0234 (2)
H8BA0.96080.01800.20680.035*
H8BB0.88360.07430.17580.035*
H8BC0.89700.11820.19870.035*
C9B0.68407 (5)0.20273 (13)0.06781 (4)0.01842 (19)
H9BA0.67720.15430.10160.022*
C10B0.62599 (5)0.26665 (14)0.03565 (4)0.01972 (19)
H10B0.62890.31160.00060.024*
C11B0.55731 (5)0.26688 (13)0.05515 (4)0.01883 (19)
C12B0.49040 (5)0.27168 (14)0.01548 (4)0.0203 (2)
H12B0.44850.30350.02850.024*
C13B0.48442 (5)0.23422 (13)0.03785 (4)0.0198 (2)
H13B0.52720.21120.05070.024*
C14B0.41874 (5)0.22514 (13)0.07822 (4)0.01829 (19)
C15B0.35178 (5)0.26085 (13)0.06460 (4)0.01829 (19)
H15B0.34840.29240.02820.022*
C16B0.29111 (5)0.24990 (13)0.10418 (4)0.01745 (19)
C17B0.29605 (5)0.20299 (13)0.15844 (4)0.01816 (19)
C18B0.36156 (6)0.16712 (13)0.17167 (4)0.0200 (2)
H18B0.36500.13480.20800.024*
C19B0.42248 (5)0.17860 (14)0.13161 (4)0.0205 (2)
H19B0.46740.15420.14100.025*
C20B0.21431 (6)0.28988 (17)0.04009 (5)0.0278 (2)
H20D0.16390.30610.03900.042*
H20E0.24160.38680.02170.042*
H20F0.23090.18200.02150.042*
C21B0.23441 (6)0.13995 (15)0.24840 (4)0.0253 (2)
H21D0.18590.13260.26910.038*
H21E0.25670.02590.24700.038*
H21F0.26170.22170.26640.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0163 (3)0.0342 (4)0.0214 (4)0.0047 (3)0.0016 (3)0.0053 (3)
O2A0.0222 (4)0.0294 (4)0.0191 (4)0.0030 (3)0.0033 (3)0.0023 (3)
O3A0.0203 (4)0.0366 (4)0.0169 (3)0.0041 (3)0.0046 (3)0.0010 (3)
O4A0.0183 (3)0.0207 (4)0.0351 (4)0.0012 (3)0.0089 (3)0.0060 (3)
O5A0.0137 (3)0.0242 (4)0.0338 (4)0.0017 (3)0.0073 (3)0.0027 (3)
O1B0.0181 (4)0.0362 (4)0.0271 (4)0.0012 (3)0.0092 (3)0.0004 (3)
O2B0.0148 (3)0.0317 (4)0.0227 (4)0.0029 (3)0.0026 (3)0.0037 (3)
O3B0.0219 (4)0.0383 (4)0.0172 (4)0.0051 (3)0.0040 (3)0.0003 (3)
O4B0.0158 (3)0.0340 (4)0.0187 (3)0.0047 (3)0.0037 (3)0.0016 (3)
O5B0.0203 (4)0.0321 (4)0.0153 (3)0.0008 (3)0.0004 (3)0.0028 (3)
C1A0.0166 (4)0.0167 (4)0.0188 (4)0.0001 (3)0.0034 (3)0.0011 (3)
C2A0.0176 (4)0.0192 (4)0.0158 (4)0.0001 (3)0.0033 (3)0.0003 (3)
C3A0.0162 (4)0.0181 (4)0.0197 (5)0.0012 (3)0.0037 (4)0.0006 (4)
C4A0.0201 (5)0.0173 (4)0.0178 (4)0.0005 (4)0.0000 (4)0.0013 (3)
C5A0.0247 (5)0.0192 (4)0.0170 (4)0.0006 (4)0.0041 (4)0.0011 (4)
C6A0.0203 (5)0.0191 (4)0.0199 (5)0.0007 (4)0.0067 (4)0.0000 (4)
C7A0.0212 (5)0.0289 (5)0.0229 (5)0.0041 (4)0.0054 (4)0.0039 (4)
C8A0.0350 (6)0.0329 (6)0.0187 (5)0.0019 (5)0.0041 (4)0.0009 (4)
C9A0.0158 (4)0.0179 (4)0.0215 (5)0.0017 (3)0.0049 (4)0.0013 (4)
C10A0.0145 (4)0.0220 (5)0.0204 (5)0.0029 (4)0.0046 (4)0.0011 (4)
C11A0.0170 (4)0.0207 (4)0.0184 (4)0.0022 (4)0.0050 (4)0.0032 (4)
C12A0.0172 (4)0.0218 (5)0.0173 (4)0.0036 (4)0.0045 (4)0.0013 (4)
C13A0.0181 (4)0.0230 (5)0.0164 (4)0.0027 (4)0.0044 (3)0.0009 (4)
C14A0.0152 (4)0.0227 (5)0.0156 (4)0.0019 (4)0.0027 (3)0.0027 (4)
C15A0.0142 (4)0.0202 (4)0.0187 (4)0.0003 (3)0.0021 (3)0.0016 (4)
C16A0.0158 (4)0.0189 (4)0.0188 (4)0.0010 (3)0.0027 (3)0.0005 (3)
C17A0.0134 (4)0.0223 (5)0.0209 (5)0.0006 (3)0.0038 (3)0.0030 (4)
C18A0.0167 (4)0.0216 (5)0.0222 (5)0.0025 (4)0.0018 (4)0.0001 (4)
C19A0.0190 (5)0.0223 (5)0.0195 (5)0.0005 (4)0.0024 (4)0.0021 (4)
C20A0.0262 (5)0.0203 (5)0.0491 (7)0.0033 (4)0.0111 (5)0.0044 (5)
C21A0.0152 (4)0.0283 (5)0.0373 (6)0.0037 (4)0.0050 (4)0.0003 (5)
C1B0.0166 (4)0.0194 (4)0.0179 (4)0.0002 (3)0.0026 (3)0.0019 (3)
C2B0.0197 (5)0.0249 (5)0.0176 (5)0.0002 (4)0.0018 (4)0.0001 (4)
C3B0.0234 (5)0.0272 (5)0.0181 (5)0.0021 (4)0.0065 (4)0.0006 (4)
C4B0.0170 (4)0.0227 (5)0.0225 (5)0.0022 (4)0.0058 (4)0.0042 (4)
C5B0.0167 (4)0.0192 (4)0.0197 (5)0.0008 (3)0.0018 (4)0.0015 (4)
C6B0.0175 (4)0.0197 (4)0.0171 (4)0.0009 (3)0.0032 (3)0.0006 (3)
C7B0.0270 (6)0.0455 (7)0.0339 (7)0.0015 (5)0.0167 (5)0.0033 (5)
C8B0.0185 (5)0.0284 (5)0.0230 (5)0.0034 (4)0.0031 (4)0.0049 (4)
C9B0.0182 (4)0.0204 (4)0.0169 (4)0.0007 (4)0.0039 (4)0.0006 (4)
C10B0.0179 (4)0.0239 (5)0.0174 (4)0.0002 (4)0.0033 (4)0.0013 (4)
C11B0.0174 (4)0.0207 (4)0.0183 (5)0.0025 (4)0.0029 (4)0.0002 (4)
C12B0.0157 (4)0.0249 (5)0.0206 (5)0.0030 (4)0.0035 (4)0.0003 (4)
C13B0.0156 (4)0.0229 (5)0.0214 (5)0.0016 (4)0.0048 (4)0.0006 (4)
C14B0.0170 (4)0.0194 (4)0.0186 (5)0.0004 (3)0.0034 (4)0.0007 (4)
C15B0.0180 (4)0.0214 (5)0.0155 (4)0.0018 (4)0.0031 (4)0.0009 (3)
C16B0.0166 (4)0.0186 (4)0.0175 (4)0.0018 (3)0.0043 (4)0.0002 (3)
C17B0.0191 (4)0.0186 (4)0.0161 (4)0.0013 (4)0.0015 (4)0.0005 (3)
C18B0.0233 (5)0.0213 (5)0.0164 (4)0.0014 (4)0.0059 (4)0.0017 (4)
C19B0.0181 (4)0.0239 (5)0.0207 (5)0.0003 (4)0.0067 (4)0.0021 (4)
C20B0.0225 (5)0.0411 (6)0.0212 (5)0.0049 (5)0.0075 (4)0.0036 (5)
C21B0.0302 (6)0.0287 (5)0.0156 (5)0.0008 (4)0.0005 (4)0.0035 (4)
Geometric parameters (Å, º) top
O1A—C3A1.3698 (12)C18A—C19A1.3956 (15)
O1A—C7A1.4277 (13)C18A—H18A0.9500
O2A—C4A1.3642 (12)C19A—H19A0.9500
O2A—C8A1.4265 (14)C20A—H20A0.9800
O3A—C11A1.2375 (13)C20A—H20B0.9800
O4A—C16A1.3633 (12)C20A—H20C0.9800
O4A—C20A1.4262 (13)C21A—H21A0.9800
O5A—C17A1.3574 (12)C21A—H21B0.9800
O5A—C21A1.4319 (13)C21A—H21C0.9800
O1B—C4B1.3654 (12)C1B—C2B1.3917 (15)
O1B—C7B1.4280 (14)C1B—C6B1.4092 (13)
O2B—C5B1.3657 (12)C1B—C9B1.4619 (14)
O2B—C8B1.4342 (13)C2B—C3B1.3933 (15)
O3B—C11B1.2310 (13)C2B—H2BA0.9500
O4B—C16B1.3655 (12)C3B—C4B1.3890 (15)
O4B—C20B1.4261 (13)C3B—H3BA0.9500
O5B—C17B1.3667 (12)C4B—C5B1.4117 (15)
O5B—C21B1.4273 (13)C5B—C6B1.3833 (14)
C1A—C6A1.3903 (14)C6B—H6BA0.9500
C1A—C2A1.4105 (14)C7B—H7BA0.9800
C1A—C9A1.4594 (13)C7B—H7BB0.9800
C2A—C3A1.3815 (13)C7B—H7BC0.9800
C2A—H2AA0.9500C8B—H8BA0.9800
C3A—C4A1.4142 (14)C8B—H8BB0.9800
C4A—C5A1.3843 (15)C8B—H8BC0.9800
C5A—C6A1.3952 (14)C9B—C10B1.3420 (14)
C5A—H5AA0.9500C9B—H9BA0.9500
C6A—H6AA0.9500C10B—C11B1.4824 (14)
C7A—H7AA0.9800C10B—H10B0.9500
C7A—H7AB0.9800C11B—C12B1.4699 (14)
C7A—H7AC0.9800C12B—C13B1.3411 (15)
C8A—H8AA0.9800C12B—H12B0.9500
C8A—H8AB0.9800C13B—C14B1.4626 (14)
C8A—H8AC0.9800C13B—H13B0.9500
C9A—C10A1.3429 (14)C14B—C19B1.3893 (14)
C9A—H9AA0.9500C14B—C15B1.4123 (14)
C10A—C11A1.4649 (13)C15B—C16B1.3833 (13)
C10A—H10A0.9500C15B—H15B0.9500
C11A—C12A1.4832 (14)C16B—C17B1.4159 (14)
C12A—C13A1.3409 (14)C17B—C18B1.3824 (14)
C12A—H12A0.9500C18B—C19B1.3935 (14)
C13A—C14A1.4578 (14)C18B—H18B0.9500
C13A—H13A0.9500C19B—H19B0.9500
C14A—C19A1.3897 (14)C20B—H20D0.9800
C14A—C15A1.4102 (14)C20B—H20E0.9800
C15A—C16A1.3813 (14)C20B—H20F0.9800
C15A—H15A0.9500C21B—H21D0.9800
C16A—C17A1.4184 (14)C21B—H21E0.9800
C17A—C18A1.3870 (15)C21B—H21F0.9800
C3A—O1A—C7A116.80 (8)H21A—C21A—H21B109.5
C4A—O2A—C8A116.57 (9)O5A—C21A—H21C109.5
C16A—O4A—C20A116.84 (9)H21A—C21A—H21C109.5
C17A—O5A—C21A116.75 (9)H21B—C21A—H21C109.5
C4B—O1B—C7B116.98 (9)C2B—C1B—C6B118.16 (9)
C5B—O2B—C8B116.16 (8)C2B—C1B—C9B123.64 (9)
C16B—O4B—C20B116.66 (8)C6B—C1B—C9B118.19 (9)
C17B—O5B—C21B117.00 (8)C1B—C2B—C3B120.82 (10)
C6A—C1A—C2A118.92 (9)C1B—C2B—H2BA119.6
C6A—C1A—C9A118.71 (9)C3B—C2B—H2BA119.6
C2A—C1A—C9A122.37 (9)C4B—C3B—C2B120.69 (10)
C3A—C2A—C1A120.14 (9)C4B—C3B—H3BA119.7
C3A—C2A—H2AA119.9C2B—C3B—H3BA119.7
C1A—C2A—H2AA119.9O1B—C4B—C3B124.82 (10)
O1A—C3A—C2A125.08 (9)O1B—C4B—C5B115.87 (9)
O1A—C3A—C4A114.65 (8)C3B—C4B—C5B119.30 (9)
C2A—C3A—C4A120.27 (9)O2B—C5B—C6B124.61 (9)
O2A—C4A—C5A125.26 (9)O2B—C5B—C4B115.98 (9)
O2A—C4A—C3A115.02 (9)C6B—C5B—C4B119.42 (9)
C5A—C4A—C3A119.71 (9)C5B—C6B—C1B121.59 (10)
C4A—C5A—C6A119.69 (9)C5B—C6B—H6BA119.2
C4A—C5A—H5AA120.2C1B—C6B—H6BA119.2
C6A—C5A—H5AA120.2O1B—C7B—H7BA109.5
C1A—C6A—C5A121.27 (9)O1B—C7B—H7BB109.5
C1A—C6A—H6AA119.4H7BA—C7B—H7BB109.5
C5A—C6A—H6AA119.4O1B—C7B—H7BC109.5
O1A—C7A—H7AA109.5H7BA—C7B—H7BC109.5
O1A—C7A—H7AB109.5H7BB—C7B—H7BC109.5
H7AA—C7A—H7AB109.5O2B—C8B—H8BA109.5
O1A—C7A—H7AC109.5O2B—C8B—H8BB109.5
H7AA—C7A—H7AC109.5H8BA—C8B—H8BB109.5
H7AB—C7A—H7AC109.5O2B—C8B—H8BC109.5
O2A—C8A—H8AA109.5H8BA—C8B—H8BC109.5
O2A—C8A—H8AB109.5H8BB—C8B—H8BC109.5
H8AA—C8A—H8AB109.5C10B—C9B—C1B127.94 (10)
O2A—C8A—H8AC109.5C10B—C9B—H9BA116.0
H8AA—C8A—H8AC109.5C1B—C9B—H9BA116.0
H8AB—C8A—H8AC109.5C9B—C10B—C11B119.72 (9)
C10A—C9A—C1A126.63 (9)C9B—C10B—H10B120.1
C10A—C9A—H9AA116.7C11B—C10B—H10B120.1
C1A—C9A—H9AA116.7O3B—C11B—C12B119.19 (9)
C9A—C10A—C11A124.72 (9)O3B—C11B—C10B120.86 (9)
C9A—C10A—H10A117.6C12B—C11B—C10B119.96 (9)
C11A—C10A—H10A117.6C13B—C12B—C11B124.44 (9)
O3A—C11A—C10A119.48 (9)C13B—C12B—H12B117.8
O3A—C11A—C12A119.69 (9)C11B—C12B—H12B117.8
C10A—C11A—C12A120.75 (9)C12B—C13B—C14B126.68 (10)
C13A—C12A—C11A119.16 (9)C12B—C13B—H13B116.7
C13A—C12A—H12A120.4C14B—C13B—H13B116.7
C11A—C12A—H12A120.4C19B—C14B—C15B119.05 (9)
C12A—C13A—C14A127.61 (10)C19B—C14B—C13B118.75 (9)
C12A—C13A—H13A116.2C15B—C14B—C13B122.20 (9)
C14A—C13A—H13A116.2C16B—C15B—C14B120.08 (9)
C19A—C14A—C15A118.97 (9)C16B—C15B—H15B120.0
C19A—C14A—C13A119.01 (9)C14B—C15B—H15B120.0
C15A—C14A—C13A122.00 (9)O4B—C16B—C15B124.98 (9)
C16A—C15A—C14A120.15 (9)O4B—C16B—C17B114.99 (8)
C16A—C15A—H15A119.9C15B—C16B—C17B120.03 (9)
C14A—C15A—H15A119.9O5B—C17B—C18B125.24 (9)
O4A—C16A—C15A124.41 (9)O5B—C17B—C16B114.89 (9)
O4A—C16A—C17A115.24 (9)C18B—C17B—C16B119.88 (9)
C15A—C16A—C17A120.35 (9)C17B—C18B—C19B119.79 (9)
O5A—C17A—C18A125.04 (9)C17B—C18B—H18B120.1
O5A—C17A—C16A115.52 (9)C19B—C18B—H18B120.1
C18A—C17A—C16A119.43 (9)C14B—C19B—C18B121.17 (9)
C17A—C18A—C19A119.79 (9)C14B—C19B—H19B119.4
C17A—C18A—H18A120.1C18B—C19B—H19B119.4
C19A—C18A—H18A120.1O4B—C20B—H20D109.5
C14A—C19A—C18A121.27 (10)O4B—C20B—H20E109.5
C14A—C19A—H19A119.4H20D—C20B—H20E109.5
C18A—C19A—H19A119.4O4B—C20B—H20F109.5
O4A—C20A—H20A109.5H20D—C20B—H20F109.5
O4A—C20A—H20B109.5H20E—C20B—H20F109.5
H20A—C20A—H20B109.5O5B—C21B—H21D109.5
O4A—C20A—H20C109.5O5B—C21B—H21E109.5
H20A—C20A—H20C109.5H21D—C21B—H21E109.5
H20B—C20A—H20C109.5O5B—C21B—H21F109.5
O5A—C21A—H21A109.5H21D—C21B—H21F109.5
O5A—C21A—H21B109.5H21E—C21B—H21F109.5
C6A—C1A—C2A—C3A0.78 (14)C6B—C1B—C2B—C3B0.80 (15)
C9A—C1A—C2A—C3A179.53 (9)C9B—C1B—C2B—C3B179.93 (10)
C7A—O1A—C3A—C2A3.51 (15)C1B—C2B—C3B—C4B1.13 (16)
C7A—O1A—C3A—C4A176.01 (9)C7B—O1B—C4B—C3B1.64 (16)
C1A—C2A—C3A—O1A179.57 (9)C7B—O1B—C4B—C5B178.82 (10)
C1A—C2A—C3A—C4A0.06 (15)C2B—C3B—C4B—O1B179.40 (10)
C8A—O2A—C4A—C5A8.28 (15)C2B—C3B—C4B—C5B0.12 (16)
C8A—O2A—C4A—C3A171.83 (9)C8B—O2B—C5B—C6B1.15 (15)
O1A—C3A—C4A—O2A1.32 (13)C8B—O2B—C5B—C4B178.23 (9)
C2A—C3A—C4A—O2A179.13 (9)O1B—C4B—C5B—O2B1.32 (14)
O1A—C3A—C4A—C5A178.78 (9)C3B—C4B—C5B—O2B178.24 (9)
C2A—C3A—C4A—C5A0.77 (15)O1B—C4B—C5B—C6B179.26 (9)
O2A—C4A—C5A—C6A179.01 (9)C3B—C4B—C5B—C6B1.18 (15)
C3A—C4A—C5A—C6A0.88 (15)O2B—C5B—C6B—C1B177.85 (9)
C2A—C1A—C6A—C5A0.67 (15)C4B—C5B—C6B—C1B1.51 (15)
C9A—C1A—C6A—C5A179.47 (9)C2B—C1B—C6B—C5B0.52 (15)
C4A—C5A—C6A—C1A0.16 (15)C9B—C1B—C6B—C5B178.78 (9)
C6A—C1A—C9A—C10A179.67 (10)C2B—C1B—C9B—C10B3.14 (17)
C2A—C1A—C9A—C10A1.58 (16)C6B—C1B—C9B—C10B176.12 (10)
C1A—C9A—C10A—C11A172.18 (9)C1B—C9B—C10B—C11B176.83 (9)
C9A—C10A—C11A—O3A170.90 (10)C9B—C10B—C11B—O3B23.27 (15)
C9A—C10A—C11A—C12A5.81 (16)C9B—C10B—C11B—C12B156.53 (10)
O3A—C11A—C12A—C13A23.71 (15)O3B—C11B—C12B—C13B162.80 (11)
C10A—C11A—C12A—C13A153.00 (10)C10B—C11B—C12B—C13B17.01 (16)
C11A—C12A—C13A—C14A178.36 (9)C11B—C12B—C13B—C14B175.38 (10)
C12A—C13A—C14A—C19A158.01 (11)C12B—C13B—C14B—C19B177.88 (11)
C12A—C13A—C14A—C15A20.32 (16)C12B—C13B—C14B—C15B1.64 (17)
C19A—C14A—C15A—C16A0.62 (14)C19B—C14B—C15B—C16B0.23 (15)
C13A—C14A—C15A—C16A177.70 (9)C13B—C14B—C15B—C16B179.76 (9)
C20A—O4A—C16A—C15A21.79 (15)C20B—O4B—C16B—C15B14.48 (15)
C20A—O4A—C16A—C17A158.30 (10)C20B—O4B—C16B—C17B165.79 (9)
C14A—C15A—C16A—O4A179.19 (9)C14B—C15B—C16B—O4B179.77 (9)
C14A—C15A—C16A—C17A0.91 (15)C14B—C15B—C16B—C17B0.05 (15)
C21A—O5A—C17A—C18A6.10 (15)C21B—O5B—C17B—C18B4.18 (15)
C21A—O5A—C17A—C16A172.56 (9)C21B—O5B—C17B—C16B175.94 (9)
O4A—C16A—C17A—O5A0.40 (13)O4B—C16B—C17B—O5B0.25 (13)
C15A—C16A—C17A—O5A179.69 (9)C15B—C16B—C17B—O5B179.49 (9)
O4A—C16A—C17A—C18A179.14 (9)O4B—C16B—C17B—C18B179.85 (9)
C15A—C16A—C17A—C18A0.94 (15)C15B—C16B—C17B—C18B0.41 (15)
O5A—C17A—C18A—C19A178.06 (10)O5B—C17B—C18B—C19B179.41 (10)
C16A—C17A—C18A—C19A0.56 (15)C16B—C17B—C18B—C19B0.48 (15)
C15A—C14A—C19A—C18A2.16 (15)C15B—C14B—C19B—C18B0.16 (16)
C13A—C14A—C19A—C18A176.22 (9)C13B—C14B—C19B—C18B179.70 (9)
C17A—C18A—C19A—C14A2.13 (16)C17B—C18B—C19B—C14B0.20 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6A—H6AA···O3Bi0.952.543.2898 (13)137
C8A—H8AC···O3Ai0.982.583.5513 (15)173
C20A—H20C···O1Ai0.982.573.5085 (15)161
C8B—H8BA···O4Aii0.982.413.2334 (13)141
C8B—H8BB···O5Biii0.982.543.4056 (14)147
C10B—H10B···O3Aiv0.952.543.4325 (13)157
C12B—H12B···O3A0.952.473.3968 (13)164
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y1, z; (iii) x+1, y, z; (iv) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC21H22O5
Mr354.39
Crystal system, space groupMonoclinic, P21/c
Temperature (K)103
a, b, c (Å)19.1646 (13), 7.7488 (5), 24.8495 (17)
β (°) 100.414 (1)
V3)3629.4 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.56 × 0.35 × 0.24
Data collection
DiffractometerCCD area-detector
Absorption correctionMulti-scan
DENZO/SCALEPACK (Otwinowski & Minor, 1997)
Tmin, Tmax0.950, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
40342, 10146, 8569
Rint0.027
(sin θ/λ)max1)0.697
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.114, 1.03
No. of reflections10146
No. of parameters477
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.29

Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXTL (Bruker, 2000).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6A—H6AA···O3Bi0.952.543.2898 (13)136.5
C8A—H8AC···O3Ai0.982.583.5513 (15)173.1
C20A—H20C···O1Ai0.982.573.5085 (15)161.0
C8B—H8BA···O4Aii0.982.413.2334 (13)140.8
C8B—H8BB···O5Biii0.982.543.4056 (14)147.0
C10B—H10B···O3Aiv0.952.543.4325 (13)156.8
C12B—H12B···O3A0.952.473.3968 (13)164.2
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y1, z; (iii) x+1, y, z; (iv) x+1, y+1, z.
 

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