4-tert-Butyl-2-(4-tert-butyl­pyridin-2-yl)pyridinium nitrate

Wu, W.-S.

doi:10.1107/S1600536811028030

organic compounds

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Volume 67| Part 8| August 2011| Page o2070

doi:10.1107/S1600536811028030

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4-tert-Butyl-2-(4-tert-butylpyridin-2-yl)pyridinium nitrate

Wen-Sheng Wu ^a ^*

^aSchool of Chemistry and Chemical Engineering, Zhaoqing University, Zhaoqing 526061, People's Republic of China
^*Correspondence e-mail: zqwswu@163.com

(Received 3 July 2011; accepted 13 July 2011; online 16 July 2011)

In the title compound, C₁₈H₂₅N₂⁺·NO₃⁻, the dihedral angle between the pyridine rings is 19.06 (10)°. In the crystal, the ions are linked into a three-dimensional network by N—H⋯O and C—H⋯O hydrogen-bonding interactions.

Related literature

For background to the coordination chemistry and applications of bipyridine and its derivatives, see: Duan et al. (2010 ); Morrow & Trogler (1989 ); Noro et al. (2000 ); Yaghi et al. (1998 ); Huertas et al. (2001 ); Qin et al. (2002 ).

Experimental

Crystal data

C₁₈H₂₅N₂⁺·NO₃⁻
M_r = 331.41
Orthorhombic, P n a 2₁
a = 11.606 (5) Å
b = 9.770 (4) Å
c = 16.199 (7) Å
V = 1836.8 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 273 K
0.29 × 0.24 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.962, T_max = 0.978
11773 measured reflections
1705 independent reflections
1314 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.112
S = 1.06
1705 reflections
227 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	1.00 (3)	1.89 (3)	2.716 (4)	137 (3)
C4—H4⋯O3ⁱⁱ	0.93	2.58	3.480 (4)	164
C7—H7⋯O3ⁱⁱ	0.93	2.49	3.389 (4)	163
C9—H9⋯O3ⁱⁱⁱ	0.93	2.60	3.385 (4)	143
Symmetry codes: (i) $[-x+1, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811028030/rz2623sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811028030/rz2623Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811028030/rz2623Isup3.cml

checkCIF report

Comment top

Metal complexes of bipyridine and its derivatives have been extensively studied because of their potential applications in catalysis (Morrow & Trogler, 1989; Noro et al., 2000) and visible light driven water oxidation (Duan et al., 2010). One of these compounds, 4,4'-di-tert-butyl-2,2'-bipyridine, has recently been used as ligand in coordination chemistry (Huertas et al., 2001; Qin et al., 2002). As a contribution to this research field, the crystal structure of the title complex containing a bipyridyl ligand is reported herein.

The asymmetric unit of the title compound (Fig. 1) consists of one 4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridinium cation and one nitrate anion. In the cation, the dihedral angle between the planes of two pyridine rings is 19.06 (10)°. In the crystal, cations and anions are linked into a three-dimensional network by N—H···O and C—H···O hydrogen bonds (Table 1).

Related literature top

For background to coordination chemistry and applications of bipyridine and its derivatives, see: Duan et al. (2010); Morrow & Trogler (1989); Noro et al. (2000); Yaghi et al. (1998); Huertas et al. (2001); Qin et al. (2002).

Experimental top

4,4'-Di-tert-butyl-2,2'-bipyridine (0.15 g, 0.56 mmol) and nitric acid (30%, 50 ml) were stirred for 20 min at 313 K.The solution was then filtered and left to evaporate slowly at room temperature. After three weeks, colourless laths and prisms of the title compound were isolated.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of title compound with displacement ellipsoids drawn at the 50% probability level.

4-tert-Butyl-2-(4-tert-butylpyridin-2-yl)pyridinium nitrate top

Crystal data top

C₁₈H₂₅N₂⁺·NO₃⁻	F(000) = 712.0
M_r = 331.41	D_x = 1.198 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1686 reflections
a = 11.606 (5) Å	θ = 2.4–25.1°
b = 9.770 (4) Å	µ = 0.08 mm⁻¹
c = 16.199 (7) Å	T = 273 K
V = 1836.8 (13) Å³	Block, colourless
Z = 4	0.29 × 0.24 × 0.19 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1705 independent reflections
Radiation source: fine-focus sealed tube	1314 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 25.2°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
T_min = 0.962, T_max = 0.978	k = −11→11
11773 measured reflections	l = −18→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.064P)² + 0.0558P] where P = (F_o² + 2F_c²)/3
1705 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.14 e Å⁻³
1 restraint	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₈H₂₅N₂⁺·NO₃⁻	V = 1836.8 (13) Å³
M_r = 331.41	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 11.606 (5) Å	µ = 0.08 mm⁻¹
b = 9.770 (4) Å	T = 273 K
c = 16.199 (7) Å	0.29 × 0.24 × 0.19 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1705 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1314 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.978	R_int = 0.042
11773 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	1 restraint
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.14 e Å⁻³
1705 reflections	Δρ_min = −0.13 e Å⁻³
227 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	0.6857 (3)	0.6853 (3)	1.06496 (18)	0.0996 (11)
O3	0.6436 (2)	0.5517 (3)	0.96612 (17)	0.0845 (9)
O2	0.7322 (3)	0.7406 (4)	0.9424 (2)	0.1063 (11)
N1	0.2126 (2)	0.0984 (3)	0.64095 (16)	0.0490 (7)
H1N	0.280 (3)	0.143 (3)	0.613 (2)	0.059 (9)*
N2	0.4248 (2)	0.1079 (3)	0.70159 (18)	0.0570 (8)
N3	0.6866 (2)	0.6606 (3)	0.9902 (2)	0.0628 (8)
C1	0.4700 (3)	0.1084 (3)	0.8731 (2)	0.0484 (8)
C2	0.5555 (3)	0.1325 (4)	0.8155 (2)	0.0626 (10)
H2	0.6306	0.1493	0.8327	0.075*
C3	0.5294 (3)	0.1316 (5)	0.7323 (3)	0.0669 (10)
H3	0.5888	0.1486	0.6952	0.080*
C4	0.3599 (3)	0.0832 (3)	0.8416 (2)	0.0455 (7)
H4	0.2988	0.0660	0.8773	0.055*
C5	0.3418 (3)	0.0838 (3)	0.7571 (2)	0.0438 (7)
C6	0.2263 (3)	0.0558 (3)	0.71989 (17)	0.0424 (7)
C7	0.1355 (2)	−0.0087 (3)	0.7586 (2)	0.0438 (7)
H7	0.1440	−0.0385	0.8128	0.053*
C8	0.1142 (3)	0.0787 (4)	0.5994 (2)	0.0569 (9)
H8	0.1078	0.1091	0.5452	0.068*
C9	0.0233 (3)	0.0144 (3)	0.6360 (2)	0.0530 (8)
H9	−0.0443	0.0001	0.6064	0.064*
C10	0.0312 (3)	−0.0301 (3)	0.71786 (19)	0.0458 (8)
C11	0.4935 (3)	0.1032 (4)	0.9658 (2)	0.0592 (9)
C12	0.6147 (4)	0.1546 (7)	0.9880 (3)	0.119 (2)
H12A	0.6713	0.0967	0.9625	0.178*
H12B	0.6245	0.1524	1.0468	0.178*
H12C	0.6241	0.2467	0.9685	0.178*
C13	0.4872 (5)	−0.0481 (5)	0.9912 (3)	0.1001 (15)
H13A	0.4117	−0.0831	0.9794	0.150*
H13B	0.5025	−0.0562	1.0492	0.150*
H13C	0.5436	−0.0994	0.9608	0.150*
C14	0.4034 (5)	0.1836 (6)	1.0136 (3)	0.1090 (18)
H14A	0.4091	0.2788	0.9996	0.163*
H14B	0.4163	0.1721	1.0717	0.163*
H14C	0.3280	0.1505	0.9996	0.163*
C15	−0.0693 (3)	−0.0977 (3)	0.7623 (2)	0.0533 (8)
C16	−0.0320 (4)	−0.2367 (4)	0.7949 (3)	0.0861 (13)
H16A	−0.0095	−0.2941	0.7496	0.129*
H16B	−0.0950	−0.2785	0.8239	0.129*
H16C	0.0319	−0.2254	0.8318	0.129*
C17	−0.1034 (4)	−0.0060 (4)	0.8356 (3)	0.0831 (13)
H17A	−0.0393	0.0027	0.8727	0.125*
H17B	−0.1674	−0.0463	0.8643	0.125*
H17C	−0.1249	0.0829	0.8156	0.125*
C18	−0.1747 (4)	−0.1165 (6)	0.7074 (4)	0.1001 (17)
H18A	−0.1979	−0.0294	0.6855	0.150*
H18B	−0.2366	−0.1547	0.7392	0.150*
H18C	−0.1561	−0.1772	0.6627	0.150*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.136 (3)	0.107 (2)	0.0558 (18)	−0.0491 (19)	0.0177 (17)	−0.0289 (16)
O3	0.097 (2)	0.094 (2)	0.0625 (18)	−0.0245 (17)	0.0054 (16)	−0.0279 (16)
O2	0.092 (2)	0.118 (2)	0.109 (3)	−0.0007 (19)	0.033 (2)	0.042 (2)
N1	0.0528 (17)	0.0565 (16)	0.0379 (15)	−0.0017 (12)	0.0009 (13)	0.0075 (12)
N2	0.0457 (16)	0.075 (2)	0.0502 (17)	−0.0018 (14)	0.0053 (14)	0.0172 (14)
N3	0.0545 (17)	0.074 (2)	0.060 (2)	0.0000 (15)	0.0104 (15)	−0.0011 (18)
C1	0.048 (2)	0.0409 (17)	0.056 (2)	−0.0002 (13)	−0.0028 (16)	0.0012 (14)
C2	0.046 (2)	0.071 (2)	0.071 (3)	−0.0058 (16)	−0.0048 (19)	0.0067 (18)
C3	0.052 (2)	0.085 (3)	0.064 (3)	−0.0027 (18)	0.0098 (19)	0.0224 (19)
C4	0.0428 (17)	0.0480 (17)	0.0458 (19)	−0.0006 (13)	0.0009 (14)	0.0000 (13)
C5	0.0462 (17)	0.0414 (16)	0.0437 (18)	0.0007 (12)	0.0028 (14)	0.0045 (13)
C6	0.0483 (18)	0.0458 (15)	0.0332 (17)	0.0039 (13)	0.0003 (13)	0.0019 (13)
C7	0.0480 (17)	0.0488 (16)	0.0344 (15)	−0.0007 (14)	−0.0008 (15)	0.0043 (13)
C8	0.071 (2)	0.062 (2)	0.0369 (18)	0.0006 (18)	−0.0048 (17)	0.0062 (15)
C9	0.0532 (19)	0.0607 (19)	0.0450 (18)	−0.0029 (15)	−0.0106 (16)	0.0019 (16)
C10	0.0502 (19)	0.0437 (17)	0.0434 (19)	0.0016 (13)	−0.0011 (14)	−0.0014 (14)
C11	0.056 (2)	0.067 (2)	0.055 (2)	0.0018 (16)	−0.0107 (17)	−0.0088 (18)
C12	0.086 (3)	0.193 (6)	0.077 (3)	−0.036 (4)	−0.022 (3)	−0.022 (4)
C13	0.131 (4)	0.106 (4)	0.063 (3)	0.003 (3)	−0.032 (3)	0.015 (3)
C14	0.112 (4)	0.147 (5)	0.068 (3)	0.044 (3)	−0.019 (3)	−0.039 (3)
C15	0.0503 (19)	0.058 (2)	0.052 (2)	−0.0104 (15)	0.0007 (17)	0.0003 (16)
C16	0.089 (3)	0.061 (2)	0.109 (3)	−0.014 (2)	0.012 (3)	0.017 (2)
C17	0.072 (3)	0.084 (3)	0.093 (3)	−0.014 (2)	0.025 (2)	−0.011 (2)
C18	0.072 (3)	0.140 (5)	0.088 (3)	−0.037 (3)	−0.014 (3)	0.006 (3)

Geometric parameters (Å, º) top

O1—N3	1.235 (4)	C11—C14	1.520 (6)
O3—N3	1.239 (4)	C11—C13	1.536 (6)
O2—N3	1.221 (4)	C11—C12	1.536 (6)
N1—C8	1.340 (4)	C12—H12A	0.9600
N1—C6	1.354 (4)	C12—H12B	0.9600
N1—H1N	1.00 (4)	C12—H12C	0.9600
N2—C3	1.332 (5)	C13—H13A	0.9600
N2—C5	1.339 (4)	C13—H13B	0.9600
C1—C2	1.383 (5)	C13—H13C	0.9600
C1—C4	1.398 (4)	C14—H14A	0.9600
C1—C11	1.527 (5)	C14—H14B	0.9600
C2—C3	1.382 (6)	C14—H14C	0.9600
C2—H2	0.9300	C15—C16	1.519 (5)
C3—H3	0.9300	C15—C18	1.524 (5)
C4—C5	1.384 (5)	C15—C17	1.540 (6)
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.495 (4)	C16—H16B	0.9600
C6—C7	1.378 (4)	C16—H16C	0.9600
C7—C10	1.395 (4)	C17—H17A	0.9600
C7—H7	0.9300	C17—H17B	0.9600
C8—C9	1.364 (5)	C17—H17C	0.9600
C8—H8	0.9300	C18—H18A	0.9600
C9—C10	1.398 (4)	C18—H18B	0.9600
C9—H9	0.9300	C18—H18C	0.9600
C10—C15	1.521 (5)

C8—N1—C6	122.0 (3)	C11—C12—H12A	109.5
C8—N1—H1N	119 (2)	C11—C12—H12B	109.5
C6—N1—H1N	118 (2)	H12A—C12—H12B	109.5
C3—N2—C5	115.8 (3)	C11—C12—H12C	109.5
O2—N3—O1	120.1 (4)	H12A—C12—H12C	109.5
O2—N3—O3	121.6 (4)	H12B—C12—H12C	109.5
O1—N3—O3	118.3 (3)	C11—C13—H13A	109.5
C2—C1—C4	116.1 (3)	C11—C13—H13B	109.5
C2—C1—C11	122.8 (3)	H13A—C13—H13B	109.5
C4—C1—C11	121.1 (3)	C11—C13—H13C	109.5
C3—C2—C1	120.0 (3)	H13A—C13—H13C	109.5
C3—C2—H2	120.0	H13B—C13—H13C	109.5
C1—C2—H2	120.0	C11—C14—H14A	109.5
N2—C3—C2	124.4 (3)	C11—C14—H14B	109.5
N2—C3—H3	117.8	H14A—C14—H14B	109.5
C2—C3—H3	117.8	C11—C14—H14C	109.5
C5—C4—C1	119.9 (3)	H14A—C14—H14C	109.5
C5—C4—H4	120.0	H14B—C14—H14C	109.5
C1—C4—H4	120.0	C16—C15—C10	109.6 (3)
N2—C5—C4	123.7 (3)	C16—C15—C18	108.9 (3)
N2—C5—C6	114.0 (3)	C10—C15—C18	113.0 (3)
C4—C5—C6	122.3 (3)	C16—C15—C17	109.0 (4)
N1—C6—C7	118.7 (3)	C10—C15—C17	108.0 (3)
N1—C6—C5	115.5 (3)	C18—C15—C17	108.3 (3)
C7—C6—C5	125.9 (3)	C15—C16—H16A	109.5
C6—C7—C10	121.1 (3)	C15—C16—H16B	109.5
C6—C7—H7	119.4	H16A—C16—H16B	109.5
C10—C7—H7	119.4	C15—C16—H16C	109.5
N1—C8—C9	120.5 (3)	H16A—C16—H16C	109.5
N1—C8—H8	119.8	H16B—C16—H16C	109.5
C9—C8—H8	119.8	C15—C17—H17A	109.5
C8—C9—C10	120.3 (3)	C15—C17—H17B	109.5
C8—C9—H9	119.8	H17A—C17—H17B	109.5
C10—C9—H9	119.8	C15—C17—H17C	109.5
C7—C10—C9	117.3 (3)	H17A—C17—H17C	109.5
C7—C10—C15	120.4 (3)	H17B—C17—H17C	109.5
C9—C10—C15	122.3 (3)	C15—C18—H18A	109.5
C14—C11—C1	111.2 (3)	C15—C18—H18B	109.5
C14—C11—C13	109.1 (4)	H18A—C18—H18B	109.5
C1—C11—C13	106.7 (3)	C15—C18—H18C	109.5
C14—C11—C12	110.0 (4)	H18A—C18—H18C	109.5
C1—C11—C12	112.5 (3)	H18B—C18—H18C	109.5
C13—C11—C12	107.2 (4)

C4—C1—C2—C3	0.4 (5)	C6—N1—C8—C9	0.2 (5)
C11—C1—C2—C3	177.9 (4)	N1—C8—C9—C10	0.9 (5)
C5—N2—C3—C2	−0.1 (6)	C6—C7—C10—C9	1.1 (4)
C1—C2—C3—N2	−0.3 (7)	C6—C7—C10—C15	−178.2 (3)
C2—C1—C4—C5	−0.2 (4)	C8—C9—C10—C7	−1.5 (5)
C11—C1—C4—C5	−177.7 (3)	C8—C9—C10—C15	177.8 (3)
C3—N2—C5—C4	0.3 (5)	C2—C1—C11—C14	135.0 (4)
C3—N2—C5—C6	−179.1 (3)	C4—C1—C11—C14	−47.6 (5)
C1—C4—C5—N2	−0.2 (5)	C2—C1—C11—C13	−106.1 (4)
C1—C4—C5—C6	179.2 (3)	C4—C1—C11—C13	71.3 (4)
C8—N1—C6—C7	−0.6 (4)	C2—C1—C11—C12	11.1 (5)
C8—N1—C6—C5	179.2 (3)	C4—C1—C11—C12	−171.5 (4)
N2—C5—C6—N1	−19.3 (4)	C7—C10—C15—C16	−56.6 (4)
C4—C5—C6—N1	161.3 (3)	C9—C10—C15—C16	124.1 (4)
N2—C5—C6—C7	160.5 (3)	C7—C10—C15—C18	−178.2 (3)
C4—C5—C6—C7	−19.0 (5)	C9—C10—C15—C18	2.5 (5)
N1—C6—C7—C10	−0.1 (4)	C7—C10—C15—C17	62.0 (4)
C5—C6—C7—C10	−179.8 (3)	C9—C10—C15—C17	−117.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	1.00 (3)	1.89 (3)	2.716 (4)	137 (3)
C4—H4···O3ⁱⁱ	0.93	2.58	3.480 (4)	164
C7—H7···O3ⁱⁱ	0.93	2.49	3.389 (4)	163
C9—H9···O3ⁱⁱⁱ	0.93	2.60	3.385 (4)	143

Symmetry codes: (i) −x+1, −y+1, z−1/2; (ii) x−1/2, −y+1/2, z; (iii) −x+1/2, y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₅N₂⁺·NO₃⁻
M_r	331.41
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	273
a, b, c (Å)	11.606 (5), 9.770 (4), 16.199 (7)
V (Å³)	1836.8 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.29 × 0.24 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.962, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	11773, 1705, 1314
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.112, 1.06
No. of reflections	1705
No. of parameters	227
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.13

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	1.00 (3)	1.89 (3)	2.716 (4)	137 (3)
C4—H4···O3ⁱⁱ	0.93	2.58	3.480 (4)	164
C7—H7···O3ⁱⁱ	0.93	2.49	3.389 (4)	163
C9—H9···O3ⁱⁱⁱ	0.93	2.60	3.385 (4)	143

Symmetry codes: (i) −x+1, −y+1, z−1/2; (ii) x−1/2, −y+1/2, z; (iii) −x+1/2, y−1/2, z−1/2.

Acknowledgements

The author gratefully acknowledges the Natural Science Foundation of Guangdong Province of China (No. 10452606101004869) and the Natural Science Foundation of Zhaoqing University (No. 0933) for financial support.

References

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