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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 66| Part 12| December 2010| Page o3183
https://doi.org/10.1107/S1600536810046350

8-Benzoyl-7-hy­dr­oxy-4-methyl-2H-1-benzo­pyran-2-one monohydrate

Shu-Ping Yang,a* Li-Jun Han,b Da-Qi Wangc and Xiao-Yun Chena

aCollege of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, bCollege of Mathematics and Science, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, and cCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: spyang69320@yahoo.cn

(Received 8 November 2010; accepted 10 November 2010; online 13 November 2010)

In the title compound, C17H12O4·H2O, the coumarin ring system is approximately planar with a maximum atomic deviation of 0.011 (2) Å, and is nearly perpendicular to the phenyl ring at a dihedral angle of 86.63 (9)°. In the crystal, mol­ecules are linked by classical O—H⋯O and weak C—H⋯O hydrogen bonds. π–π stacking is also present [centroid–centroid distance = 3.6898 (12) Å].

Related literature

For the biological activity of coumarins, see: Sharma et al. (2005[Sharma, S. D., Rajor, H. K., Chopra, S. & Sharma, R. K. (2005). Biometals, 18, 143-154.]); Iqbal et al. (2009[Iqbal, P. F., Bhat, A. R. & Azam, A. (2009). Eur. J. Med. Chem. 44, 2252-2259.]); Siddiqui et al. (2009[Siddiqui, N., Arshad, M. F. & Khan, S. A. (2009). Acta Pol. Pharm. Drug Res. 66, 161-167.]); Vyas et al. (2009[Vyas, K. B., Nimavat, K. S., Jani, G. R. & Hathi, M. V. (2009). Orbital, 1, 183-192.]); Rollinger et al. (2004[Rollinger, J. M., Hornick, A., Langer, T., Stuppner, H. & Prast, H. (2004). J. Med. Chem. 47, 6248-6254.]); Brühlmann et al. (2001[Brühlmann, C., Ooms, F., Carrupt, P.-A., Testa, B., Catto, M., Leonetti, F., Altomare, C. & Carotti, A. (2001). J. Med. Chem. 44, 3195-3198.]). For related structures, see: Yang et al. (2006[Yang, S.-P., Han, L.-J., Wang, D.-Q. & Ding, T.-Z. (2006). Acta Cryst. E62, o5196-o5198.], 2007[Yang, S.-P., Han, L.-J., Wang, D.-Q. & Xia, H.-T. (2007). Acta Cryst. E63, o4785.], 2008[Yang, S.-P., Wang, D.-Q., Han, L.-J. & Liu, Y.-F. (2008). Acta Cryst. E64, o2088.]).

[Scheme 1]

Experimental

Crystal data

  • C17H12O4·H2O

  • Mr = 298.28

  • Monoclinic, C 2/c

  • a = 14.8912 (15) Å

  • b = 9.6768 (11) Å

  • c = 20.644 (2) Å

  • β = 104.275 (2)°

  • V = 2882.9 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 298 K

  • 0.49 × 0.24 × 0.21 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.952, Tmax = 0.979

  • 7271 measured reflections

  • 2549 independent reflections

  • 1706 reflections with I > 2σ(I)

  • Rint = 0.036
Refinement

  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.110

  • S = 1.05

  • 2549 reflections

  • 255 parameters

  • All H-atom parameters refined

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H3⋯O5i 0.93 (3) 1.72 (3) 2.650 (2) 177 (3)
O5—H5A⋯O2 0.91 (4) 2.00 (4) 2.887 (3) 166 (3)
O5—H5B⋯O4ii 0.87 (3) 2.03 (3) 2.875 (2) 162 (3)
C17—H17⋯O2iii 0.95 (2) 2.54 (2) 3.422 (3) 154.7 (16)
Symmetry codes: (i) x, y+1, z; (ii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810046350/xu5087sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046350/xu5087Isup2.hkl

checkCIF report


Comment top

Coumarins are very well known for their biological activity, such as antioxidants (Sharma et al., 2005), antiamoebic (Iqbal et al., 2009), anticonvulsant activity (Siddiqui et al., 2009), antimicrobial (Vyas et al., 2009) and inhibitions of acetylcholinesterase and monoamine oxidase (Rollinger et al., 2004; Brühlmann et al., 2001). The crystal structures of some coumarin derivatives (Yang et al., 2006; 2007; 2008) have been decribed. As part of our study of the crystal structures of coumarin derivatives with 7-hydroxy, we report here the crystal structure of 8-Benzoyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one, (I).

In the molecule(I), the asymmetric unit of (I) contains one coumarin molecule and one hydration water molecules, and which are linked together by one O—H···O hydrogen bond (Table 1 and Fig. 1). The coumarin moiety and phenyl ring (two r.m.s deviations 0.0060 Å) are perpendicular to each other with a dihedral angle of 86.59 (5)° between the plane of the atoms O1—O3/C1—C9 and the plane of C12—C17.

In crystal structure of (I), translationally related molecules are linked together by O3—H3···O5i [symmetry code: (i)x, 1 + y, z] hydrogen bond, forming C(10) chains parallel to the b axis; inversionally related molecular chains are linked together by O—H···O hydrogen bond O5—H5B···O4ii [symmetry codes: (ii)1/2 - x, 1/2 - y, 1 - z], generating doubled chain of R56(28)[R44(20)R44(16)] ring parallel to the b axis (Table.1 and Fig. 2). Neighboring doubled chains are linked into three-dimensional crystal structure by π–π interaction Cg1···Cg1iii [Where Cg1 is the centroid of O1/C1—C4/C9, Cg1···Cg1iii = 3.6898 (12) Å, symmetry code: (iii) -x, y,1/2 - z].

Related literature top

The title compound is a coumarin derivative; for the biological activity of coumarins, see: Sharma et al. (2005); Iqbal et al. (2009); Siddiqui et al. (2009); Vyas et al. (2009); Rollinger et al. (2004); Brühlmann et al. (2001). For related structures, see: Yang et al. (2006, 2007, 2008).

Experimental top

The mixture containing 2.8 g (10 mmol) of dry, powdered 7-benzoxy-4-methylcoumarin and 4.53 g (34 mmol) of anhydrous aluminium chloride was heated at 463 K for 2 h in an oil bath, then 30 ml of dilute (1:7) hydrochloric acid is added and the mixture is heated on a steam bath for 30 min, the crude product was filtered off, washed with water. Colorless crystals of (I) suitable for X-ray structure analysis were obtained by recrystallizing from 95% water-ethanol solution [m.p. 492 K].

Refinement top

All H atom was located in a difference Fourier map and refined freely.

Structure description top

Coumarins are very well known for their biological activity, such as antioxidants (Sharma et al., 2005), antiamoebic (Iqbal et al., 2009), anticonvulsant activity (Siddiqui et al., 2009), antimicrobial (Vyas et al., 2009) and inhibitions of acetylcholinesterase and monoamine oxidase (Rollinger et al., 2004; Brühlmann et al., 2001). The crystal structures of some coumarin derivatives (Yang et al., 2006; 2007; 2008) have been decribed. As part of our study of the crystal structures of coumarin derivatives with 7-hydroxy, we report here the crystal structure of 8-Benzoyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one, (I).

In the molecule(I), the asymmetric unit of (I) contains one coumarin molecule and one hydration water molecules, and which are linked together by one O—H···O hydrogen bond (Table 1 and Fig. 1). The coumarin moiety and phenyl ring (two r.m.s deviations 0.0060 Å) are perpendicular to each other with a dihedral angle of 86.59 (5)° between the plane of the atoms O1—O3/C1—C9 and the plane of C12—C17.

In crystal structure of (I), translationally related molecules are linked together by O3—H3···O5i [symmetry code: (i)x, 1 + y, z] hydrogen bond, forming C(10) chains parallel to the b axis; inversionally related molecular chains are linked together by O—H···O hydrogen bond O5—H5B···O4ii [symmetry codes: (ii)1/2 - x, 1/2 - y, 1 - z], generating doubled chain of R56(28)[R44(20)R44(16)] ring parallel to the b axis (Table.1 and Fig. 2). Neighboring doubled chains are linked into three-dimensional crystal structure by π–π interaction Cg1···Cg1iii [Where Cg1 is the centroid of O1/C1—C4/C9, Cg1···Cg1iii = 3.6898 (12) Å, symmetry code: (iii) -x, y,1/2 - z].

The title compound is a coumarin derivative; for the biological activity of coumarins, see: Sharma et al. (2005); Iqbal et al. (2009); Siddiqui et al. (2009); Vyas et al. (2009); Rollinger et al. (2004); Brühlmann et al. (2001). For related structures, see: Yang et al. (2006, 2007, 2008).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of title structure, showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme, intramolecular O–H···O contact is shown.
[Figure 2] Fig. 2. The molecular doubled chain of R56(28)[R44 (20)R44(16)]ring parallel to the b axis. [Symmetry codes: (i) x, 1 + y, z; (ii)1/2 - x, 1/2 - y, 1 - z].
8-Benzoyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one monohydrate top
Crystal data top
C17H12O4·H2OF(000) = 1248
Mr = 298.28Dx = 1.374 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2106 reflections
a = 14.8912 (15) Åθ = 2.6–26.3°
b = 9.6768 (11) ŵ = 0.10 mm−1
c = 20.644 (2) ÅT = 298 K
β = 104.275 (2)°Prism, colorless
V = 2882.9 (5) Å30.49 × 0.24 × 0.21 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer		2549 independent reflections
Radiation source: fine-focus sealed tube1706 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −17→14
Tmin = 0.952, Tmax = 0.979k = −11→11
7271 measured reflectionsl = −24→24
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110All H-atom parameters refined
S = 1.05 w = 1/[σ2(Fo2) + (0.0463P)2 + 1.197P]
where P = (Fo2 + 2Fc2)/3
2549 reflections(Δ/σ)max = 0.001
255 parametersΔρmax = 0.15 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C17H12O4·H2OV = 2882.9 (5) Å3
Mr = 298.28Z = 8
Monoclinic, C2/cMo Kα radiation
a = 14.8912 (15) ŵ = 0.10 mm−1
b = 9.6768 (11) ÅT = 298 K
c = 20.644 (2) Å0.49 × 0.24 × 0.21 mm
β = 104.275 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2549 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1706 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 0.979Rint = 0.036
7271 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.110All H-atom parameters refined
S = 1.05Δρmax = 0.15 e Å−3
2549 reflectionsΔρmin = −0.19 e Å−3
255 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
O10.17438 (9)0.30443 (14)0.31197 (6)0.0429 (4)
O20.13299 (12)0.09551 (16)0.27504 (8)0.0590 (5)
O30.27345 (10)0.73405 (18)0.40667 (7)0.0516 (4)
H30.2699 (19)0.830 (3)0.4027 (13)0.093 (10)*
O40.23351 (10)0.42720 (19)0.46551 (7)0.0621 (5)
C10.12717 (15)0.2185 (2)0.26211 (10)0.0443 (5)
C20.07607 (15)0.2814 (2)0.20096 (10)0.0453 (6)
H20.0427 (14)0.218 (2)0.1671 (10)0.050 (6)*
C30.07320 (13)0.4192 (2)0.19106 (9)0.0397 (5)
C40.12370 (13)0.5072 (2)0.24429 (9)0.0367 (5)
C50.12629 (15)0.6515 (2)0.24161 (11)0.0436 (5)
H50.0918 (13)0.697 (2)0.2017 (10)0.042 (5)*
C60.17489 (14)0.7290 (2)0.29421 (11)0.0438 (5)
H60.1748 (14)0.829 (2)0.2898 (10)0.050 (6)*
C70.22368 (14)0.6637 (2)0.35315 (10)0.0395 (5)
C80.22316 (13)0.5202 (2)0.35827 (9)0.0364 (5)
C90.17343 (13)0.4459 (2)0.30380 (9)0.0359 (5)
C100.01805 (19)0.4821 (3)0.12713 (12)0.0522 (6)
H10A−0.0231 (17)0.414 (3)0.0985 (12)0.074 (8)*
H10B−0.0219 (17)0.555 (3)0.1356 (12)0.071 (8)*
H10C0.0575 (16)0.525 (3)0.1039 (12)0.064 (8)*
C110.27364 (14)0.4473 (2)0.42133 (9)0.0390 (5)
C120.37057 (13)0.4036 (2)0.42734 (9)0.0360 (5)
H130.3868 (14)0.308 (2)0.5173 (11)0.056 (7)*
C130.41872 (16)0.3316 (2)0.48382 (11)0.0484 (6)
C140.51066 (17)0.2977 (3)0.49076 (13)0.0568 (7)
H140.5453 (14)0.250 (2)0.5300 (11)0.057 (6)*
C150.55516 (17)0.3334 (3)0.44212 (12)0.0552 (6)
H150.6208 (17)0.309 (2)0.4484 (11)0.063 (7)*
C160.50801 (16)0.4022 (3)0.38535 (12)0.0523 (6)
H160.5390 (16)0.430 (2)0.3503 (12)0.070 (7)*
C170.41556 (15)0.4371 (2)0.37787 (10)0.0417 (5)
H170.3830 (13)0.483 (2)0.3384 (10)0.046 (6)*
O50.25946 (14)0.00677 (18)0.39756 (10)0.0631 (5)
H5A0.220 (2)0.049 (4)0.3623 (17)0.125 (13)*
H5B0.258 (2)0.045 (3)0.4355 (16)0.101 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0533 (9)0.0359 (9)0.0360 (8)0.0039 (7)0.0042 (6)0.0021 (6)
O20.0815 (12)0.0410 (10)0.0500 (9)0.0009 (9)0.0076 (8)0.0008 (8)
O30.0539 (10)0.0458 (11)0.0477 (9)−0.0017 (8)−0.0015 (7)−0.0047 (8)
O40.0535 (10)0.0921 (13)0.0436 (9)0.0117 (9)0.0173 (8)0.0148 (8)
C10.0524 (14)0.0411 (14)0.0403 (12)0.0011 (11)0.0133 (10)−0.0015 (10)
C20.0499 (14)0.0491 (15)0.0357 (12)−0.0010 (11)0.0086 (10)−0.0057 (10)
C30.0376 (12)0.0496 (14)0.0324 (10)0.0032 (10)0.0095 (9)0.0010 (10)
C40.0360 (11)0.0409 (13)0.0327 (10)0.0051 (9)0.0078 (9)0.0034 (9)
C50.0431 (13)0.0445 (14)0.0393 (12)0.0072 (11)0.0031 (10)0.0094 (11)
C60.0454 (13)0.0354 (13)0.0479 (13)0.0045 (10)0.0065 (10)0.0046 (10)
C70.0366 (12)0.0425 (13)0.0383 (11)0.0014 (10)0.0074 (9)−0.0020 (10)
C80.0351 (11)0.0401 (13)0.0339 (10)0.0035 (9)0.0080 (9)0.0017 (9)
C90.0373 (11)0.0340 (12)0.0374 (11)0.0049 (9)0.0108 (9)0.0027 (9)
C100.0494 (15)0.0626 (18)0.0403 (13)0.0049 (14)0.0029 (12)0.0046 (12)
C110.0427 (12)0.0404 (12)0.0329 (11)−0.0018 (10)0.0076 (9)−0.0017 (9)
C120.0390 (11)0.0333 (12)0.0329 (10)−0.0020 (9)0.0039 (9)−0.0018 (9)
C130.0480 (14)0.0536 (15)0.0419 (12)0.0010 (11)0.0079 (11)0.0088 (11)
C140.0501 (15)0.0607 (17)0.0526 (15)0.0086 (12)−0.0007 (12)0.0109 (12)
C150.0391 (14)0.0596 (16)0.0636 (16)0.0030 (12)0.0064 (12)−0.0049 (13)
C160.0473 (14)0.0588 (16)0.0534 (14)−0.0038 (12)0.0176 (12)−0.0056 (12)
C170.0464 (13)0.0402 (13)0.0363 (11)−0.0016 (10)0.0065 (10)0.0000 (10)
O50.0828 (13)0.0548 (12)0.0488 (11)0.0045 (9)0.0106 (10)−0.0027 (9)
Geometric parameters (Å, º) top
O1—C11.374 (2)C8—C111.509 (3)
O1—C91.379 (2)C10—H10A0.99 (3)
O2—C11.218 (2)C10—H10B0.96 (3)
O3—C71.352 (2)C10—H10C0.94 (2)
O3—H30.93 (3)C11—C121.479 (3)
O4—C111.223 (2)C12—C171.391 (3)
C1—C21.438 (3)C12—C131.395 (3)
C2—C31.348 (3)C13—C141.381 (3)
C2—H20.97 (2)C13—H130.96 (2)
C3—C41.446 (3)C14—C151.376 (3)
C3—C101.501 (3)C14—H140.96 (2)
C4—C51.398 (3)C15—C161.380 (3)
C4—C91.400 (3)C15—H150.98 (2)
C5—C61.370 (3)C16—C171.389 (3)
C5—H50.96 (2)C16—H160.99 (2)
C6—C71.404 (3)C17—H170.95 (2)
C6—H60.97 (2)O5—H5A0.91 (4)
C7—C81.393 (3)O5—H5B0.87 (3)
C8—C91.385 (3)
C1—O1—C9121.41 (15)C3—C10—H10A112.3 (14)
C7—O3—H3114.9 (17)C3—C10—H10B111.4 (15)
O2—C1—O1115.56 (19)H10A—C10—H10B106 (2)
O2—C1—C2126.8 (2)C3—C10—H10C110.6 (14)
O1—C1—C2117.6 (2)H10A—C10—H10C111 (2)
C3—C2—C1122.8 (2)H10B—C10—H10C105 (2)
C3—C2—H2121.6 (12)O4—C11—C12122.57 (18)
C1—C2—H2115.7 (12)O4—C11—C8119.13 (18)
C2—C3—C4118.45 (18)C12—C11—C8118.30 (16)
C2—C3—C10121.6 (2)C17—C12—C13119.26 (19)
C4—C3—C10119.9 (2)C17—C12—C11120.57 (18)
C5—C4—C9116.35 (19)C13—C12—C11120.15 (17)
C5—C4—C3124.92 (19)C14—C13—C12119.8 (2)
C9—C4—C3118.73 (19)C14—C13—H13121.6 (13)
C6—C5—C4122.0 (2)C12—C13—H13118.6 (13)
C6—C5—H5119.5 (12)C15—C14—C13120.5 (2)
C4—C5—H5118.5 (12)C15—C14—H14118.6 (12)
C5—C6—C7120.0 (2)C13—C14—H14120.8 (12)
C5—C6—H6118.9 (12)C14—C15—C16120.3 (2)
C7—C6—H6121.1 (12)C14—C15—H15119.2 (13)
O3—C7—C8116.86 (18)C16—C15—H15120.5 (13)
O3—C7—C6123.0 (2)C15—C16—C17119.7 (2)
C8—C7—C6120.16 (19)C15—C16—H16121.4 (14)
C9—C8—C7117.90 (18)C17—C16—H16118.9 (14)
C9—C8—C11120.69 (19)C16—C17—C12120.4 (2)
C7—C8—C11121.40 (18)C16—C17—H17119.5 (12)
O1—C9—C8115.39 (16)C12—C17—H17120.1 (12)
O1—C9—C4121.00 (17)H5A—O5—H5B112 (3)
C8—C9—C4123.60 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O5i0.93 (3)1.72 (3)2.650 (2)177 (3)
O5—H5A···O20.91 (4)2.00 (4)2.887 (3)166 (3)
O5—H5B···O4ii0.87 (3)2.03 (3)2.875 (2)162 (3)
C17—H17···O2iii0.95 (2)2.54 (2)3.422 (3)154.7 (16)
Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, −y+1/2, −z+1; (iii) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC17H12O4·H2O
Mr298.28
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)14.8912 (15), 9.6768 (11), 20.644 (2)
β (°) 104.275 (2)
V (Å3)2882.9 (5)
Z8
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.49 × 0.24 × 0.21
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.952, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections		7271, 2549, 1706
Rint0.036
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.110, 1.05
No. of reflections2549
No. of parameters255
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.15, −0.19

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O5i0.93 (3)1.72 (3)2.650 (2)177 (3)
O5—H5A···O20.91 (4)2.00 (4)2.887 (3)166 (3)
O5—H5B···O4ii0.87 (3)2.03 (3)2.875 (2)162 (3)
C17—H17···O2iii0.95 (2)2.54 (2)3.422 (3)154.7 (16)
Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, −y+1/2, −z+1; (iii) −x+1/2, y+1/2, −z+1/2.
 

Acknowledgements

The authors acknowledge the financial support of the Huaihai Institute of Technology Science Foundation (No. KX10019).

References

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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3183
https://doi.org/10.1107/S1600536810046350
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