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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 12| December 2008| Page o2419
doi:10.1107/S1600536808038403

2-(4-Di­methyl­amino-2-hy­droxy­benzoyl)benzoic acid methanol solvate

Jin-Chun Guo,a Qing-Hao Liu,b* Jin-Ying Guo,c Mei-Zhu Chenb and Rui-Wang Zhangb

aQinghai Institute of Salt Lakes, Chinese Academy of Sciences, Xining 810008, People's Republic of China, bSchool of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, People's Republic of China, and cCollege of Food and Bioengineering, He'nan University of Science and Technology, Luoyang 471003, People's Republic of China
*Correspondence e-mail: liuqinghao0205@126.com

(Received 11 November 2008; accepted 18 November 2008; online 22 November 2008)

In the title compound, C16H15NO4·CH4O, the dihedral angle between the benzene rings is 75.21 (5)°. The structure is stabilized by an intra­molecular O—H⋯O inter­action [O⋯O = 2.589 (2) Å]. The solvent mol­ecule links symmetry-related mol­ecules of the complex via hydrogen bonds with O⋯O separations of 2.631 (2) and 2.815 (2) Å. C—H⋯O hydrogen bonds are also present.

Related literature

For a related structure, see: Yan et al. (2006[Yan, F.-Y., Ge, F.-Y., Jin-Peng, W., Xi-Long, Y. & Guo-Yi, B. (2006). Acta Cryst. E62, o1509-o1510.]). For synthetic applications, see: Hellmut & Lamm (1977[Hellmut, K. & Lamm, G. (1977). Ger. Patent No. 2603101.]); Minru et al. (1977[Minru, K., Yoshimasa, M. & Yoshikazu, M. (1977). Jpn. Patent No. 52035688.]); Yojiro et al. (1992[Yojiro, K., Hiroshi, T., Yuichi, T., Sayuri, W., Junichi, T., Tsuneto, E. & Mansuke, M. (1992). Jpn. Patent No. 04019183.]); Lee et al. (1998[Lee, L., Benson, S. C., Rosenblum, B. B. & Spurgeon, S. L. (1998). US Patent No. 5847162.]); Luo et al. (1994[Luo, H. P., Pan, J. L. & Lu, W. L. (1994). J. Zhejiang Univ. Sci. 28, 349-354.]).

[Scheme 1]

Experimental

Crystal data

  • C16H15NO4·CH4O

  • Mr = 317.33

  • Triclinic, [P \overline 1]

  • a = 7.1438 (14) Å

  • b = 7.3021 (15) Å

  • c = 16.613 (3) Å

  • α = 83.92 (3)°

  • β = 80.21 (3)°

  • γ = 64.94 (3)°

  • V = 773.0 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 113 (2) K

  • 0.20 × 0.18 × 0.12 mm
Data collection

  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.]) Tmin = 0.980, Tmax = 0.988

  • 12548 measured reflections

  • 3528 independent reflections

  • 2679 reflections with I > 2σ(I)

  • Rint = 0.034
Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.109

  • S = 1.06

  • 3528 reflections

  • 220 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O2 0.92 (2) 1.75 (2) 2.589 (2) 151 (1)
O4—H4⋯O5i 0.94 (2) 1.70 (2) 2.631 (2) 168 (2)
O5—H5⋯O2 0.87 (2) 1.95 (2) 2.815 (2) 178 (2)
C7—H7B⋯O3ii 0.98 2.54 3.463 (2) 156
C13—H13⋯O5iii 0.95 2.53 3.331 (2) 142
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y, -z; (iii) x, y+1, z.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038403/pv2121sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038403/pv2121Isup2.hkl

checkCIF report


Comment top

The title compound, (I), is an intermediate in the synthesis of rhodamine derivatives (Hellmut & Lamm, 1977; Minru et al., 1977; Yojiro et al., 1992; Lee et al., 1998). 2-Carboxyl-4'-diethylamino-2'-hydroxybenzophenone was synthesized (Luo et al., 1994) from 3-diethylaminophenol and phthalic anhydride in toluene with the same reaction mechanism as the title compound. In the present paper, the title compound has been synthesized and the crystal structure of (I) is reported.

The bond distances and bond angles in (I) (Fig. 1) are similar to the corresponding dimensions reported for a closely related structure, 2-[4-(diethylamino)-2-hydroxybenzoyl]-3,4,5,6-tetrafluorobenzoic acid (Yan et al., 2006). The 2-hydroxy-4-dimethylaminobenzoyl and o-benzoic acid moieties in (I) are each essentially planar and the angle between two planes is 75.21 (5)°. There are intermolecular O—H···O hydrogen bonds involving the solvent and the complex molecules stabilizing the structure (Table 1 and Fig. 2). The structure also contains an intramolecular interaction of the type O—H···O (O···O = 2.589 (2) Å) and non-classical hydrogen bonds of the type C—H···O.

Related literature top

For a related structure, see: Yan et al. (2006). For synthetic applications, see: Hellmut & Lamm (1977); Minru et al. (1977); Yojiro et al. (1992); Lee et al. (1998); Luo et al. (1994).

Experimental top

A solution of 3-dimethylamino phenol (4.11 g, 30.0 mmol) and phthalic anhydride (4.66 g, 31.5 mmol) in toluene (30 ml) was refluxed for 3 h. The solution was cooled to room temperature and the precipitate was collected to afford the title compound (yield = 75.6%). The crude product was purified by silica-gel chromatography (methanol–dichloromethane, 1:50). Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution in methanol and dichloromethane (5:1).

Refinement top

The O-bound H atoms were located in a difference map and their coordinates were refined with Uiso(H) = 1.5Ueq(O). The methyl and aryl H atoms were constrained to ideal geometry with C—H distances of 0.95 and 0.98 Å, and Uiso(H) = 1.5 and 1.2Ueq(C), respectively, and each methyl group was allowed to rotate freely about its C—C bond.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level (arbitrary spheres for the H atoms).
[Figure 2] Fig. 2. The unit cell packing of (I); dashed lines indicate hydrogen-bond interactions.
2-(4-Dimethylamino-2-hydroxybenzoyl)benzoic acid methanol solvate top
Crystal data top
C16H14NO4·CH4OZ = 2
Mr = 317.33F(000) = 336
Triclinic, P1Dx = 1.363 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1438 (14) ÅCell parameters from 2451 reflections
b = 7.3021 (15) Åθ = 2.5–27.5°
c = 16.613 (3) ŵ = 0.10 mm−1
α = 83.92 (3)°T = 113 K
β = 80.21 (3)°Block, yellow
γ = 64.94 (3)°0.20 × 0.18 × 0.12 mm
V = 773.0 (3) Å3
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		3528 independent reflections
Radiation source: rotating anode2679 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.034
Detector resolution: 7.31 pixels mm-1θmax = 27.5°, θmin = 2.5°
ω and ϕ scansh = −9→9
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −9→9
Tmin = 0.980, Tmax = 0.988l = −21→21
12548 measured reflections
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0647P)2 + 0.0542P]
where P = (Fo2 + 2Fc2)/3
3528 reflections(Δ/σ)max = 0.002
220 parametersΔρmax = 0.31 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
Crystal data top
C16H14NO4·CH4Oγ = 64.94 (3)°
Mr = 317.33V = 773.0 (3) Å3
Triclinic, P1Z = 2
a = 7.1438 (14) ÅMo Kα radiation
b = 7.3021 (15) ŵ = 0.10 mm−1
c = 16.613 (3) ÅT = 113 K
α = 83.92 (3)°0.20 × 0.18 × 0.12 mm
β = 80.21 (3)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		3528 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2679 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.988Rint = 0.034
12548 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.31 e Å−3
3528 reflectionsΔρmin = −0.25 e Å−3
220 parameters
Special details top

Experimental. 1H NMR (CD3OD:CDCl3, 5:1, δ, p.p.m.): 8.07 (d, 1H), 7.68 (t, 1H), 7.59 (t, 1H), 7.36 (d, 1H), 6.88 (d, 1H), 6.18 (d, 1H), 6.13 (s, 1H), 3.04 (s, 6H).

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
O10.70462 (14)−0.28138 (12)0.19780 (5)0.0243 (2)
H10.651 (2)−0.228 (2)0.2486 (10)0.036*
O20.54875 (13)−0.02370 (12)0.31294 (5)0.0228 (2)
O30.88960 (13)0.13445 (13)0.30456 (5)0.0267 (2)
O40.83287 (14)0.32743 (14)0.40966 (6)0.0345 (2)
H40.973 (3)0.242 (3)0.4146 (10)0.052*
O50.21609 (13)0.11128 (13)0.44162 (5)0.0245 (2)
H50.322 (3)0.069 (2)0.4029 (10)0.037*
N10.81331 (15)−0.03715 (16)−0.07467 (6)0.0245 (2)
C10.61529 (16)0.07774 (16)0.17518 (7)0.0172 (2)
C20.60924 (17)0.23363 (17)0.11636 (7)0.0192 (2)
H20.56110.36740.13420.023*
C30.66995 (18)0.19999 (18)0.03453 (7)0.0211 (2)
H30.66020.3099−0.00320.025*
C40.74787 (17)−0.00015 (18)0.00592 (7)0.0203 (2)
C50.75624 (17)−0.15813 (17)0.06392 (7)0.0206 (2)
H5A0.8070−0.29230.04610.025*
C60.69205 (17)−0.12142 (16)0.14605 (7)0.0184 (2)
C70.7924 (2)0.1273 (2)−0.13552 (7)0.0286 (3)
H7A0.64540.2228−0.13250.043*
H7B0.84220.0720−0.19020.043*
H7C0.87540.1975−0.12470.043*
C80.9050 (2)−0.2431 (2)−0.10245 (8)0.0283 (3)
H8A1.0167−0.3284−0.07040.042*
H8B0.9627−0.2441−0.16040.042*
H8C0.7975−0.2956−0.09530.042*
C90.54677 (17)0.11448 (17)0.26072 (7)0.0177 (2)
C100.45044 (17)0.32664 (16)0.29110 (6)0.0165 (2)
C110.24430 (18)0.44749 (17)0.28008 (7)0.0216 (2)
H110.17610.40210.24760.026*
C120.13725 (18)0.63378 (17)0.31616 (7)0.0228 (3)
H12−0.00300.71560.30790.027*
C130.23498 (18)0.70024 (17)0.36419 (7)0.0226 (3)
H130.16150.82700.38930.027*
C140.44038 (18)0.58132 (17)0.37548 (7)0.0204 (2)
H140.50680.62720.40860.024*
C150.55075 (17)0.39511 (16)0.33878 (6)0.0168 (2)
C160.77429 (17)0.27111 (16)0.34857 (7)0.0185 (2)
C170.2575 (2)0.2154 (2)0.49935 (7)0.0287 (3)
H17A0.15890.35810.49860.043*
H17B0.40040.20520.48510.043*
H17C0.24180.15450.55410.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0321 (5)0.0178 (4)0.0208 (4)−0.0080 (4)−0.0025 (4)−0.0044 (3)
O20.0310 (5)0.0189 (4)0.0175 (4)−0.0093 (4)−0.0025 (3)−0.0021 (3)
O30.0226 (4)0.0258 (4)0.0254 (4)−0.0014 (4)−0.0052 (3)−0.0090 (4)
O40.0214 (5)0.0383 (5)0.0411 (6)−0.0025 (4)−0.0116 (4)−0.0211 (4)
O50.0207 (4)0.0280 (5)0.0251 (4)−0.0089 (4)−0.0022 (3)−0.0083 (4)
N10.0215 (5)0.0316 (6)0.0169 (5)−0.0071 (4)−0.0011 (4)−0.0064 (4)
C10.0155 (5)0.0189 (6)0.0173 (5)−0.0062 (4)−0.0030 (4)−0.0042 (4)
C20.0170 (5)0.0191 (5)0.0203 (5)−0.0059 (4)−0.0017 (4)−0.0045 (4)
C30.0186 (6)0.0234 (6)0.0191 (5)−0.0068 (5)−0.0020 (4)−0.0008 (4)
C40.0127 (5)0.0288 (6)0.0175 (5)−0.0054 (5)−0.0023 (4)−0.0063 (5)
C50.0179 (5)0.0211 (6)0.0220 (6)−0.0054 (5)−0.0028 (4)−0.0083 (4)
C60.0161 (5)0.0191 (6)0.0205 (5)−0.0063 (4)−0.0047 (4)−0.0032 (4)
C70.0255 (6)0.0406 (8)0.0170 (5)−0.0111 (6)−0.0017 (5)−0.0027 (5)
C80.0265 (6)0.0397 (7)0.0223 (6)−0.0161 (6)0.0031 (5)−0.0158 (5)
C90.0157 (5)0.0188 (5)0.0190 (5)−0.0061 (4)−0.0045 (4)−0.0032 (4)
C100.0193 (5)0.0161 (5)0.0132 (5)−0.0064 (4)−0.0011 (4)−0.0021 (4)
C110.0219 (6)0.0232 (6)0.0192 (5)−0.0071 (5)−0.0057 (4)−0.0044 (4)
C120.0190 (6)0.0215 (6)0.0228 (6)−0.0026 (5)−0.0045 (4)−0.0023 (5)
C130.0238 (6)0.0170 (5)0.0234 (6)−0.0052 (5)−0.0007 (5)−0.0041 (4)
C140.0224 (6)0.0184 (6)0.0220 (5)−0.0095 (5)−0.0029 (4)−0.0038 (4)
C150.0182 (5)0.0169 (5)0.0154 (5)−0.0077 (4)−0.0012 (4)−0.0005 (4)
C160.0201 (5)0.0181 (5)0.0186 (5)−0.0088 (5)−0.0025 (4)−0.0022 (4)
C170.0283 (6)0.0366 (7)0.0220 (6)−0.0129 (6)−0.0028 (5)−0.0079 (5)
Geometric parameters (Å, º) top
O1—C61.3550 (14)C7—H7A0.9800
O1—H10.92 (2)C7—H7B0.9800
O2—C91.2561 (14)C7—H7C0.9800
O3—C161.2092 (14)C8—H8A0.9800
O4—C161.3240 (14)C8—H8B0.9800
O4—H40.94 (2)C8—H8C0.9800
O5—C171.4237 (15)C9—C101.5075 (16)
O5—H50.87 (2)C10—C111.3919 (16)
N1—C41.3569 (15)C10—C151.4041 (15)
N1—C81.4537 (17)C11—C121.3892 (17)
N1—C71.4587 (17)C11—H110.9500
C1—C21.4105 (16)C12—C131.3850 (17)
C1—C61.4258 (16)C12—H120.9500
C1—C91.4367 (15)C13—C141.3862 (17)
C2—C31.3699 (16)C13—H130.9500
C2—H20.9500C14—C151.3950 (16)
C3—C41.4281 (17)C14—H140.9500
C3—H30.9500C15—C161.4928 (16)
C4—C51.4101 (17)C17—H17A0.9800
C5—C61.3800 (16)C17—H17B0.9800
C5—H5A0.9500C17—H17C0.9800
C6—O1—H1105.2 (9)N1—C8—H8C109.5
C16—O4—H4109.9 (10)H8A—C8—H8C109.5
C17—O5—H5109.8 (10)H8B—C8—H8C109.5
C4—N1—C8120.41 (11)O2—C9—C1122.52 (10)
C4—N1—C7121.24 (10)O2—C9—C10116.45 (9)
C8—N1—C7118.35 (10)C1—C9—C10120.82 (10)
C2—C1—C6116.93 (10)C11—C10—C15119.40 (10)
C2—C1—C9122.49 (10)C11—C10—C9117.74 (10)
C6—C1—C9120.58 (10)C15—C10—C9122.31 (10)
C3—C2—C1122.67 (10)C12—C11—C10120.65 (11)
C3—C2—H2118.7C12—C11—H11119.7
C1—C2—H2118.7C10—C11—H11119.7
C2—C3—C4120.04 (11)C13—C12—C11120.03 (11)
C2—C3—H3120.0C13—C12—H12120.0
C4—C3—H3120.0C11—C12—H12120.0
N1—C4—C5121.05 (11)C12—C13—C14119.83 (11)
N1—C4—C3120.88 (11)C12—C13—H13120.1
C5—C4—C3118.07 (10)C14—C13—H13120.1
C6—C5—C4121.21 (11)C13—C14—C15120.80 (11)
C6—C5—H5A119.4C13—C14—H14119.6
C4—C5—H5A119.4C15—C14—H14119.6
O1—C6—C5117.56 (10)C14—C15—C10119.28 (10)
O1—C6—C1121.36 (10)C14—C15—C16120.61 (10)
C5—C6—C1121.08 (11)C10—C15—C16120.10 (10)
N1—C7—H7A109.5O3—C16—O4123.78 (11)
N1—C7—H7B109.5O3—C16—C15123.12 (10)
H7A—C7—H7B109.5O4—C16—C15113.10 (10)
N1—C7—H7C109.5O5—C17—H17A109.5
H7A—C7—H7C109.5O5—C17—H17B109.5
H7B—C7—H7C109.5H17A—C17—H17B109.5
N1—C8—H8A109.5O5—C17—H17C109.5
N1—C8—H8B109.5H17A—C17—H17C109.5
H8A—C8—H8B109.5H17B—C17—H17C109.5
C6—C1—C2—C31.11 (16)C6—C1—C9—C10−175.35 (9)
C9—C1—C2—C3−178.47 (10)O2—C9—C10—C11−97.87 (12)
C1—C2—C3—C4−1.53 (17)C1—C9—C10—C1176.97 (14)
C8—N1—C4—C5−3.56 (16)O2—C9—C10—C1573.53 (14)
C7—N1—C4—C5175.95 (10)C1—C9—C10—C15−111.62 (12)
C8—N1—C4—C3175.95 (10)C15—C10—C11—C12−0.42 (16)
C7—N1—C4—C3−4.54 (16)C9—C10—C11—C12171.25 (10)
C2—C3—C4—N1−178.45 (10)C10—C11—C12—C13−0.52 (17)
C2—C3—C4—C51.08 (16)C11—C12—C13—C140.63 (18)
N1—C4—C5—C6179.25 (10)C12—C13—C14—C150.20 (17)
C3—C4—C5—C6−0.27 (16)C13—C14—C15—C10−1.13 (16)
C4—C5—C6—O1179.85 (10)C13—C14—C15—C16177.71 (10)
C4—C5—C6—C1−0.12 (17)C11—C10—C15—C141.23 (16)
C2—C1—C6—O1179.77 (9)C9—C10—C15—C14−170.04 (10)
C9—C1—C6—O1−0.65 (16)C11—C10—C15—C16−177.62 (10)
C2—C1—C6—C5−0.27 (16)C9—C10—C15—C1611.12 (15)
C9—C1—C6—C5179.32 (10)C14—C15—C16—O3−162.76 (11)
C2—C1—C9—O2178.74 (10)C10—C15—C16—O316.06 (16)
C6—C1—C9—O2−0.82 (17)C14—C15—C16—O416.69 (15)
C2—C1—C9—C104.21 (16)C10—C15—C16—O4−164.48 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.92 (2)1.75 (2)2.589 (2)151 (1)
O4—H4···O5i0.94 (2)1.70 (2)2.631 (2)168 (2)
O5—H5···O20.87 (2)1.95 (2)2.815 (2)178 (2)
C7—H7B···O3ii0.982.543.463 (2)156
C13—H13···O5iii0.952.533.331 (2)142
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y, −z; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC16H14NO4·CH4O
Mr317.33
Crystal system, space groupTriclinic, P1
Temperature (K)113
a, b, c (Å)7.1438 (14), 7.3021 (15), 16.613 (3)
α, β, γ (°)83.92 (3), 80.21 (3), 64.94 (3)
V (Å3)773.0 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.20 × 0.18 × 0.12
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.980, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections		12548, 3528, 2679
Rint0.034
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.109, 1.06
No. of reflections3528
No. of parameters220
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.31, −0.25

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalStructure (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.92 (2)1.75 (2)2.589 (2)151 (1)
O4—H4···O5i0.94 (2)1.70 (2)2.631 (2)168 (2)
O5—H5···O20.87 (2)1.95 (2)2.815 (2)178 (2)
C7—H7B···O3ii0.982.543.463 (2)156
C13—H13···O5iii0.952.533.331 (2)142
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y, −z; (iii) x, y+1, z.
 

References

First citationHellmut, K. & Lamm, G. (1977). Ger. Patent No. 2603101.  Google Scholar
 First citationLee, L., Benson, S. C., Rosenblum, B. B. & Spurgeon, S. L. (1998). US Patent No. 5847162.  Google Scholar
 First citationLuo, H. P., Pan, J. L. & Lu, W. L. (1994). J. Zhejiang Univ. Sci. 28, 349–354.  CAS Google Scholar
 First citationMinru, K., Yoshimasa, M. & Yoshikazu, M. (1977). Jpn. Patent No. 52035688.  Google Scholar
 First citationRigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
 First citationSheldrick, G. M. (1996). SADABS University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationYan, F.-Y., Ge, F.-Y., Jin-Peng, W., Xi-Long, Y. & Guo-Yi, B. (2006). Acta Cryst. E62, o1509–o1510.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationYojiro, K., Hiroshi, T., Yuichi, T., Sayuri, W., Junichi, T., Tsuneto, E. & Mansuke, M. (1992). Jpn. Patent No. 04019183.  Google Scholar

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ISSN: 2056-9890
Volume 64| Part 12| December 2008| Page o2419
doi:10.1107/S1600536808038403
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