3,5-Dimeth­oxy-N,N-bis­(2-pyridylmeth­yl)aniline

Li, H.; Dai, X.; Sun, J.

doi:10.1107/S1600536809048685

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3139

doi:10.1107/S1600536809048685

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3,5-Dimethoxy-N,N-bis(2-pyridylmethyl)aniline

Hongjuan Li,^a ^* Xianping Dai ^a and Jufeng Sun ^a

^aSchool of Pharmacy, Binzhou Medical College, Yantai 264003, People's Republic of China
^*Correspondence e-mail: hjli80@163.com

(Received 12 November 2009; accepted 16 November 2009; online 21 November 2009)

In the title molecule, C₂₀H₂₁N₃O₂, the benzene ring forms dihedral angles of 80.8 (1) and 83.5 (1)° with the two terminal pyridine rings. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link the molecules into chains propagating in [001].

Related literature

For general background to organic ligand-based crystal materials, see: Desiraju (2007 ); Moulton & Zaworotko (2001 ). For related structures, see: Frisch & Cahil (2008 ); Shattock et al. (2008 ); Shirman et al. (2008 ).

Experimental

Crystal data

C₂₀H₂₁N₃O₂
M_r = 335.40
Monoclinic, P 2₁ /c
a = 15.630 (3) Å
b = 5.9562 (12) Å
c = 20.088 (4) Å
β = 111.55 (3)°
V = 1739.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 113 K
0.27 × 0.25 × 0.20 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.978, T_max = 0.983
14749 measured reflections
4106 independent reflections
3258 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.113
S = 1.10
4106 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2ⁱ	0.95	2.49	3.3050 (15)	144
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048685/cv2657sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048685/cv2657Isup2.hkl

checkCIF report

Comment top

In recent years, considerable research has been put into the design and elaboration of new organic ligand-based crystal materials because of their importance in supramolecular chemistry, materials science and solid-state chemistry (Desiraju, 2007; Moulton & Zaworotko, 2001). It is well known that the construction of such materials strongly depends on the nature of organic bridging units. In this regard, considerable attention has been devoted to the design of new functional N-heterocyclic organic bridging units. Among of them, pyridines are useful building blocks, which are frequently employed in the construction of some interesting metal-organic frameworks and organic crystals (Frisch & Cahil, 2008; Shattock et al., 2008; Shirman et al., 2008). Herein, we report a new pyridine compound which could be applied for the preparation of metal-organic and organic crystals.

In the title molecule, (I) (Fig. 1), two pyridine rings form dihedral angles of 80.8 (1) and 83.5 (1)°, respectively, with the central benzene ring. The intermolecular C—H···O interaction (Table 1) links adjacent molecules into chains along the direction [001].

Related literature top

For general background toorganic ligand-based crystal materials, see: Desiraju (2007); Moulton & Zaworotko (2001). For related structures, see: Frisch & Cahil (2008); Shattock et al. (2008); Shirman et al. (2008).

Experimental top

3,5-Dimethoxyaniline (73.9 mg, 0.6 mmol) and 5 N NaOH (0.8 ml) were added to the solution of 2-bromomethylprydine (0.525 g, 3.05 mmol) in 1 ml of water, the obtained mixture was stirred vigorously for 24 h at room temperature. Then the mixture was extracted with 15 ml of CH₂Cl₂ for three times and the combined organic layers were dried over anhydrous Na₂SO₄. The crude material was purified by column chromatography on silica gel eluting with petroleum ether/EtOAc (3/1, V/V) to afford the desired product as a yellow solid (0.12 g, 58%). ¹H NMR (400 MHz, CDCl₃): δ = 3.64 (s, 6H), 4.82 (s, 4H), 5.87 (s, 3H), 7.14 (t, J = 6.4 Hz, 2H), 7.29 (s, 2H), 7.64 (t, J = 7.6 Hz, 2H), 8.58 (d, J = 4.4 Hz, 2H).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering.

3,5-Dimethoxy-N,N-bis(2-pyridylmethyl)aniline top

Crystal data top

C₂₀H₂₁N₃O₂	F(000) = 712
M_r = 335.40	D_x = 1.281 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4823 reflections
a = 15.630 (3) Å	θ = 2.2–27.9°
b = 5.9562 (12) Å	µ = 0.08 mm⁻¹
c = 20.088 (4) Å	T = 113 K
β = 111.55 (3)°	Block, colourless
V = 1739.3 (6) Å³	0.27 × 0.25 × 0.20 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4106 independent reflections
Radiation source: rotating anode	3258 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.038
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.1°
ω and ϕ scans	h = −20→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −7→7
T_min = 0.978, T_max = 0.983	l = −26→26
14749 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0655P)²] where P = (F_o² + 2F_c²)/3
4106 reflections	(Δ/σ)_max = 0.001
228 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₀H₂₁N₃O₂	V = 1739.3 (6) Å³
M_r = 335.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.630 (3) Å	µ = 0.08 mm⁻¹
b = 5.9562 (12) Å	T = 113 K
c = 20.088 (4) Å	0.27 × 0.25 × 0.20 mm
β = 111.55 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4106 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3258 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.983	R_int = 0.038
14749 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.10	Δρ_max = 0.22 e Å⁻³
4106 reflections	Δρ_min = −0.21 e Å⁻³
228 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

	x	y	z	U_iso*/U_eq
O1	0.46394 (5)	0.69311 (15)	0.32987 (5)	0.0298 (2)
O2	0.67567 (5)	0.25014 (13)	0.51460 (4)	0.0262 (2)
N1	0.79174 (6)	0.85369 (16)	0.41961 (5)	0.0225 (2)
N2	0.76094 (6)	1.11713 (16)	0.24609 (5)	0.0232 (2)
N3	0.98074 (6)	0.69084 (17)	0.58297 (5)	0.0270 (2)
C1	0.56528 (7)	0.47409 (19)	0.42047 (6)	0.0225 (2)
H1	0.5142	0.3882	0.4208	0.027*
C2	0.55351 (7)	0.65475 (19)	0.37374 (6)	0.0223 (2)
C3	0.62677 (7)	0.78159 (19)	0.37172 (6)	0.0215 (2)
H3	0.6168	0.9019	0.3387	0.026*
C4	0.71674 (7)	0.72922 (18)	0.41968 (6)	0.0195 (2)
C5	0.72901 (7)	0.55021 (18)	0.46686 (6)	0.0203 (2)
H5	0.7889	0.5140	0.4995	0.024*
C6	0.65369 (7)	0.42403 (18)	0.46634 (6)	0.0204 (2)
C7	0.60170 (8)	0.1182 (2)	0.51853 (7)	0.0298 (3)
H7A	0.5602	0.2138	0.5326	0.045*
H7B	0.6261	−0.0012	0.5540	0.045*
H7C	0.5679	0.0513	0.4716	0.045*
C8	0.44478 (8)	0.8805 (2)	0.28219 (7)	0.0334 (3)
H8A	0.4656	1.0189	0.3098	0.050*
H8B	0.3784	0.8893	0.2550	0.050*
H8C	0.4772	0.8618	0.2490	0.050*
C9	0.78119 (8)	1.03228 (18)	0.36833 (6)	0.0226 (2)
H9A	0.8346	1.1346	0.3873	0.027*
H9B	0.7254	1.1196	0.3637	0.027*
C10	0.77348 (7)	0.95312 (18)	0.29448 (6)	0.0196 (2)
C11	0.78065 (8)	0.72861 (19)	0.27911 (6)	0.0260 (3)
H11	0.7887	0.6166	0.3145	0.031*
C12	0.77589 (9)	0.6707 (2)	0.21078 (7)	0.0317 (3)
H12	0.7814	0.5183	0.1990	0.038*
C13	0.76299 (9)	0.8373 (2)	0.16036 (6)	0.0308 (3)
H13	0.7597	0.8028	0.1133	0.037*
C14	0.75496 (8)	1.0555 (2)	0.18028 (6)	0.0271 (3)
H14	0.7445	1.1696	0.1451	0.033*
C15	0.88451 (7)	0.7731 (2)	0.45984 (6)	0.0234 (3)
H15A	0.9269	0.8364	0.4383	0.028*
H15B	0.8854	0.6077	0.4553	0.028*
C16	0.91979 (7)	0.83373 (19)	0.53877 (6)	0.0210 (2)
C17	1.01752 (8)	0.7486 (2)	0.65253 (7)	0.0306 (3)
H17	1.0602	0.6481	0.6846	0.037*
C18	0.99727 (8)	0.9438 (2)	0.68009 (7)	0.0317 (3)
H18	1.0265	0.9791	0.7294	0.038*
C19	0.93321 (8)	1.0875 (2)	0.63410 (7)	0.0327 (3)
H19	0.9168	1.2229	0.6514	0.039*
C20	0.89329 (8)	1.0310 (2)	0.56236 (6)	0.0272 (3)
H20	0.8484	1.1260	0.5298	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0161 (4)	0.0381 (5)	0.0312 (5)	−0.0010 (3)	0.0040 (3)	0.0086 (4)
O2	0.0244 (4)	0.0261 (5)	0.0271 (4)	−0.0037 (3)	0.0083 (3)	0.0054 (3)
N1	0.0175 (5)	0.0297 (5)	0.0204 (5)	−0.0037 (4)	0.0069 (4)	0.0031 (4)
N2	0.0220 (5)	0.0220 (5)	0.0235 (5)	−0.0002 (4)	0.0058 (4)	0.0019 (4)
N3	0.0217 (5)	0.0299 (6)	0.0281 (5)	0.0012 (4)	0.0075 (4)	0.0028 (4)
C1	0.0184 (5)	0.0268 (6)	0.0234 (6)	−0.0056 (4)	0.0090 (4)	−0.0015 (5)
C2	0.0177 (5)	0.0289 (6)	0.0200 (5)	0.0005 (4)	0.0066 (4)	−0.0014 (5)
C3	0.0208 (5)	0.0243 (6)	0.0199 (5)	−0.0005 (4)	0.0082 (4)	0.0012 (4)
C4	0.0188 (5)	0.0233 (6)	0.0182 (5)	−0.0030 (4)	0.0089 (4)	−0.0046 (4)
C5	0.0166 (5)	0.0248 (6)	0.0190 (5)	−0.0006 (4)	0.0058 (4)	−0.0023 (4)
C6	0.0242 (6)	0.0210 (6)	0.0173 (5)	−0.0013 (4)	0.0093 (4)	−0.0018 (4)
C7	0.0315 (7)	0.0280 (6)	0.0317 (7)	−0.0062 (5)	0.0137 (5)	0.0036 (5)
C8	0.0237 (6)	0.0366 (7)	0.0342 (7)	0.0031 (5)	0.0040 (5)	0.0092 (6)
C9	0.0227 (5)	0.0220 (6)	0.0248 (6)	−0.0050 (4)	0.0109 (5)	−0.0017 (5)
C10	0.0147 (5)	0.0217 (6)	0.0220 (5)	−0.0023 (4)	0.0062 (4)	0.0003 (4)
C11	0.0338 (6)	0.0201 (6)	0.0268 (6)	−0.0021 (5)	0.0142 (5)	0.0030 (5)
C12	0.0460 (7)	0.0209 (6)	0.0321 (7)	−0.0032 (5)	0.0190 (6)	−0.0039 (5)
C13	0.0400 (7)	0.0305 (7)	0.0235 (6)	−0.0057 (5)	0.0135 (5)	−0.0032 (5)
C14	0.0300 (6)	0.0262 (6)	0.0218 (6)	−0.0036 (5)	0.0056 (5)	0.0039 (5)
C15	0.0162 (5)	0.0305 (6)	0.0247 (6)	−0.0033 (4)	0.0091 (4)	−0.0020 (5)
C16	0.0143 (5)	0.0239 (6)	0.0252 (6)	−0.0033 (4)	0.0076 (4)	0.0006 (5)
C17	0.0214 (6)	0.0402 (7)	0.0278 (6)	0.0024 (5)	0.0062 (5)	0.0070 (6)
C18	0.0232 (6)	0.0474 (8)	0.0228 (6)	−0.0051 (5)	0.0065 (5)	−0.0037 (6)
C19	0.0307 (7)	0.0334 (7)	0.0347 (7)	−0.0018 (5)	0.0129 (6)	−0.0090 (6)
C20	0.0217 (6)	0.0277 (6)	0.0297 (6)	0.0024 (5)	0.0063 (5)	0.0003 (5)

Geometric parameters (Å, º) top

O1—C2	1.3719 (14)	C8—H8B	0.9800
O1—C8	1.4290 (15)	C8—H8C	0.9800
O2—C6	1.3733 (13)	C9—C10	1.5185 (15)
O2—C7	1.4237 (14)	C9—H9A	0.9900
N1—C4	1.3872 (14)	C9—H9B	0.9900
N1—C9	1.4475 (14)	C10—C11	1.3862 (16)
N1—C15	1.4577 (14)	C11—C12	1.3905 (17)
N2—C10	1.3408 (14)	C11—H11	0.9500
N2—C14	1.3417 (15)	C12—C13	1.3788 (17)
N3—C16	1.3411 (15)	C12—H12	0.9500
N3—C17	1.3458 (16)	C13—C14	1.3794 (18)
C1—C6	1.3827 (16)	C13—H13	0.9500
C1—C2	1.3949 (16)	C14—H14	0.9500
C1—H1	0.9500	C15—C16	1.5185 (16)
C2—C3	1.3847 (15)	C15—H15A	0.9900
C3—C4	1.4169 (16)	C15—H15B	0.9900
C3—H3	0.9500	C16—C20	1.3859 (16)
C4—C5	1.3923 (15)	C17—C18	1.3738 (18)
C5—C6	1.3935 (15)	C17—H17	0.9500
C5—H5	0.9500	C18—C19	1.3816 (18)
C7—H7A	0.9800	C18—H18	0.9500
C7—H7B	0.9800	C19—C20	1.3852 (17)
C7—H7C	0.9800	C19—H19	0.9500
C8—H8A	0.9800	C20—H20	0.9500

C2—O1—C8	118.28 (9)	N1—C9—H9B	108.6
C6—O2—C7	117.23 (9)	C10—C9—H9B	108.6
C4—N1—C9	121.20 (9)	H9A—C9—H9B	107.6
C4—N1—C15	119.49 (9)	N2—C10—C11	122.92 (10)
C9—N1—C15	117.81 (9)	N2—C10—C9	114.84 (9)
C10—N2—C14	116.99 (10)	C11—C10—C9	122.23 (10)
C16—N3—C17	116.98 (11)	C10—C11—C12	118.68 (11)
C6—C1—C2	117.86 (10)	C10—C11—H11	120.7
C6—C1—H1	121.1	C12—C11—H11	120.7
C2—C1—H1	121.1	C13—C12—C11	119.13 (12)
O1—C2—C3	123.36 (10)	C13—C12—H12	120.4
O1—C2—C1	114.32 (10)	C11—C12—H12	120.4
C3—C2—C1	122.31 (10)	C12—C13—C14	118.00 (11)
C2—C3—C4	119.01 (10)	C12—C13—H13	121.0
C2—C3—H3	120.5	C14—C13—H13	121.0
C4—C3—H3	120.5	N2—C14—C13	124.25 (11)
N1—C4—C5	120.32 (10)	N2—C14—H14	117.9
N1—C4—C3	120.64 (10)	C13—C14—H14	117.9
C5—C4—C3	119.04 (10)	N1—C15—C16	113.97 (9)
C4—C5—C6	120.21 (10)	N1—C15—H15A	108.8
C4—C5—H5	119.9	C16—C15—H15A	108.8
C6—C5—H5	119.9	N1—C15—H15B	108.8
O2—C6—C1	124.25 (10)	C16—C15—H15B	108.8
O2—C6—C5	114.19 (9)	H15A—C15—H15B	107.7
C1—C6—C5	121.56 (10)	N3—C16—C20	122.72 (11)
O2—C7—H7A	109.5	N3—C16—C15	115.94 (10)
O2—C7—H7B	109.5	C20—C16—C15	121.27 (10)
H7A—C7—H7B	109.5	N3—C17—C18	124.13 (11)
O2—C7—H7C	109.5	N3—C17—H17	117.9
H7A—C7—H7C	109.5	C18—C17—H17	117.9
H7B—C7—H7C	109.5	C17—C18—C19	118.20 (12)
O1—C8—H8A	109.5	C17—C18—H18	120.9
O1—C8—H8B	109.5	C19—C18—H18	120.9
H8A—C8—H8B	109.5	C18—C19—C20	118.94 (12)
O1—C8—H8C	109.5	C18—C19—H19	120.5
H8A—C8—H8C	109.5	C20—C19—H19	120.5
H8B—C8—H8C	109.5	C19—C20—C16	119.00 (11)
N1—C9—C10	114.49 (9)	C19—C20—H20	120.5
N1—C9—H9A	108.6	C16—C20—H20	120.5
C10—C9—H9A	108.6

C8—O1—C2—C3	−3.27 (16)	C14—N2—C10—C11	0.28 (16)
C8—O1—C2—C1	177.50 (10)	C14—N2—C10—C9	179.13 (9)
C6—C1—C2—O1	179.80 (10)	N1—C9—C10—N2	178.10 (9)
C6—C1—C2—C3	0.56 (17)	N1—C9—C10—C11	−3.04 (15)
O1—C2—C3—C4	179.59 (10)	N2—C10—C11—C12	0.90 (17)
C1—C2—C3—C4	−1.24 (17)	C9—C10—C11—C12	−177.88 (10)
C9—N1—C4—C5	176.48 (9)	C10—C11—C12—C13	−0.87 (18)
C15—N1—C4—C5	10.78 (15)	C11—C12—C13—C14	−0.28 (18)
C9—N1—C4—C3	−3.31 (16)	C10—N2—C14—C13	−1.55 (17)
C15—N1—C4—C3	−169.01 (10)	C12—C13—C14—N2	1.56 (19)
C2—C3—C4—N1	−179.48 (10)	C4—N1—C15—C16	−83.43 (13)
C2—C3—C4—C5	0.72 (16)	C9—N1—C15—C16	110.39 (11)
N1—C4—C5—C6	−179.36 (10)	C17—N3—C16—C20	−1.19 (16)
C3—C4—C5—C6	0.44 (16)	C17—N3—C16—C15	175.75 (9)
C7—O2—C6—C1	−1.89 (16)	N1—C15—C16—N3	150.93 (10)
C7—O2—C6—C5	178.13 (10)	N1—C15—C16—C20	−32.08 (14)
C2—C1—C6—O2	−179.33 (10)	C16—N3—C17—C18	−0.83 (18)
C2—C1—C6—C5	0.65 (16)	N3—C17—C18—C19	1.91 (19)
C4—C5—C6—O2	178.84 (9)	C17—C18—C19—C20	−0.95 (18)
C4—C5—C6—C1	−1.15 (17)	C18—C19—C20—C16	−0.90 (18)
C4—N1—C9—C10	−79.37 (13)	N3—C16—C20—C19	2.06 (17)
C15—N1—C9—C10	86.56 (12)	C15—C16—C20—C19	−174.73 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2ⁱ	0.95	2.49	3.3050 (15)	144

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁N₃O₂
M_r	335.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	15.630 (3), 5.9562 (12), 20.088 (4)
β (°)	111.55 (3)
V (Å³)	1739.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.27 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.978, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	14749, 4106, 3258
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.113, 1.10
No. of reflections	4106
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2ⁱ	0.95	2.49	3.3050 (15)	144

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

The authors are grateful to the Binzhou Medical College for financial support (grant No. BY2007KJ13).

References

Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Desiraju, G. R. (2007). Angew. Chem. Int. Ed. 45, 8342–8356. Web of Science CrossRef Google Scholar
Frisch, M. & Cahil, C. L. (2008). Cryst. Growth. Des. 8, 2921–2928. Web of Science CSD CrossRef CAS Google Scholar
Moulton, B. & Zaworotko, M. J. (2001). Chem. Rev. 101, 1629–1658. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Shattock, T. R., Arora, K. K., Vishweshwar, P. & Zaworotko, M. J. (2008). Cryst. Growth. Des. 8, 4533–4545. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shirman, T., Lamere, J.-F., Shimon, L. J. W., Gupta, T., Martin, J. M. L. & van der Boom, M. E. (2008). Cryst. Growth. Des. 8, 3066–3072. Web of Science CSD CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar