(4,4′-Di-tert-butyl-2,2′-bipyridine-κ2N,N′)bis­(nitrato-κ2O,O′)copper(II)

Xiao, X.; Rao, Z.-Y.; Zhang, Y.-Q.; Xue, S.-F.; Tao, Z.

doi:10.1107/S1600536809001457

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m202

doi:10.1107/S1600536809001457

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(4,4′-Di-tert-butyl-2,2′-bipyridine-κ²N,N′)bis(nitrato-κ²O,O′)copper(II)

Xin Xiao,^a Zai-Ying Rao,^a Yun-Qiang Zhang,^a Sai-Feng Xue ^a and Zhu Tao ^b ^*

^aKey Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, People's Republic of China, and ^bInstitute of Applied Chemistry, Guizhou University, Guiyang 550025, People's Republic of China
^*Correspondence e-mail: gyhxxiaoxin@163.com

(Received 11 January 2009; accepted 12 January 2009; online 17 January 2009)

In the crystal of the title compound, [Cu(NO₃)₂(C₁₈H₂₄N₂)], the Cu^II ion is coordinated by two N atoms of the bipyridine ligand and four O atoms from the two nitrate anions in a distorted octahedral fashion. The dihedral angle between the planes of the two pyridine rings is 11.52 (10)°. In the crystal structure, weak C—H⋯O interactions may help to establish the packing.

Related literature

For general background, see: Noro et al. (2000 ); Yaghi et al. (1998 ); Huertas et al. (2001 ); Qin et al. (2002 ).

Experimental

Crystal data

[Cu(NO₃)₂(C₁₈H₂₄N₂)]
M_r = 455.96
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.8265 (16) Å
b = 13.247 (2) Å
c = 16.138 (3) Å
V = 2100.7 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.08 mm⁻¹
T = 173 (2) K
0.27 × 0.25 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.759, T_max = 0.837
11065 measured reflections
3642 independent reflections
3450 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.074
S = 1.05
3642 reflections
258 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.81 e Å⁻³
Absolute structure: Flack (1983 ), 1522 Friedel pairs
Flack parameter: 0.012 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O4ⁱ	0.93	2.46	3.124 (3)	129
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536809001457/at2708sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001457/at2708Isup2.hkl

checkCIF report

Comment top

Research into transition metal complexes has been rapidly expanding because of their fascinating structural diversity, as well as their potential applications as functional materials and enzymes (Noro et al., 2000; Yaghi et al., 1998). And 4,4'-di-tert-butyl-2,2'-bipyridine has been used as a ligand in coordination chemistry (Huertas et al., 2001; Qin et al., 2002). We report here the crystal structure of the title copper(II)complex, (I), containing a bipyridine ligand.

In the crystal of (I), the Cu^II ion is coordinated by two N atoms of the 4,4'-di-tert-butyl-2,2'-bipyridine ligand and four O atoms from the two nitrate anions. The dihedral angle between the planes of two pyridine rings is 11.52 (10)°. The title compound forms intermolecular H bond whereas the protonated C1 atom act as hydrogen-bond donor and O4 atom act as hydrogen-bond acceptor, the distance of the C1—H1···O4 hydrogen bonds is 3.124 (3) Å (Table 1). Weak C—H···O interactions may help to establish the packing.

Related literature top

For general background, see: Noro et al. (2000); Yaghi et al. (1998); Huertas et al. (2001); Qin et al. (2002).

Experimental top

A solution of 4,4'-di-tert-butyl-2,2'-bipyridine (0.15 g, 0.56 mmol) in ethanol (50 ml) was added to a solution of Cu(N0₃)₂, (0.09 g, 0.56 mmol) in H₂O (20 ml), and the resulting blue solution was stirred for 10 min at 313 K. Then, it was left to evaporate slowly at room temperature. After one week, blue crystals of (I) 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 (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

(4,4'-Di-tert-butyl-2,2'-bipyridine-κ²N,N')bis(nitrato- κ²O,O')copper(II) top

Crystal data top

[Cu(NO₃)₂(C₁₈H₂₄N₂)]	F(000) = 948
M_r = 455.96	D_x = 1.442 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2120 reflections
a = 9.8265 (16) Å	θ = 2.0–25.0°
b = 13.247 (2) Å	µ = 1.08 mm⁻¹
c = 16.138 (3) Å	T = 173 K
V = 2100.7 (6) Å³	Block, blue
Z = 4	0.27 × 0.25 × 0.17 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3642 independent reflections
Radiation source: fine-focus sealed tube	3450 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
T_min = 0.759, T_max = 0.837	k = −15→15
11065 measured reflections	l = −19→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0386P)² + 0.8717P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3642 reflections	Δρ_max = 0.64 e Å⁻³
258 parameters	Δρ_min = −0.81 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1522 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.012 (13)

Crystal data top

[Cu(NO₃)₂(C₁₈H₂₄N₂)]	V = 2100.7 (6) Å³
M_r = 455.96	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.8265 (16) Å	µ = 1.08 mm⁻¹
b = 13.247 (2) Å	T = 173 K
c = 16.138 (3) Å	0.27 × 0.25 × 0.17 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3642 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3450 reflections with I > 2σ(I)
T_min = 0.759, T_max = 0.837	R_int = 0.022
11065 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.074	Δρ_max = 0.64 e Å⁻³
S = 1.05	Δρ_min = −0.81 e Å⁻³
3642 reflections	Absolute structure: Flack (1983), 1522 Freidel pairs
258 parameters	Absolute structure parameter: 0.012 (13)
1 restraint

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
Cu1	0.58577 (3)	0.98172 (2)	0.72968 (2)	0.02515 (10)
O2	0.3672 (2)	1.0193 (2)	0.66313 (14)	0.0434 (6)
O1	0.4195 (2)	0.89792 (15)	0.74670 (14)	0.0387 (5)
O4	0.5221 (2)	1.08313 (16)	0.81065 (13)	0.0328 (5)
N2	0.7365 (2)	1.06673 (17)	0.68765 (15)	0.0243 (5)
N4	0.5626 (2)	1.05068 (18)	0.88143 (15)	0.0300 (6)
O5	0.6358 (2)	0.97414 (17)	0.88213 (13)	0.035
N1	0.6896 (2)	0.87411 (17)	0.67467 (15)	0.0242 (5)
N3	0.3281 (3)	0.9442 (2)	0.70369 (17)	0.0381 (6)
O6	0.5273 (3)	1.0950 (2)	0.94430 (15)	0.0558 (7)
C15	1.0722 (3)	1.2220 (2)	0.56813 (19)	0.0308 (7)
C6	0.8337 (3)	1.0146 (2)	0.64671 (16)	0.0225 (6)
C11	0.9809 (3)	0.6535 (2)	0.58589 (19)	0.0279 (6)
O3	0.2114 (2)	0.9132 (2)	0.7046 (2)	0.0649 (9)
C2	0.7514 (3)	0.7040 (2)	0.64459 (18)	0.0275 (6)
H2	0.7265	0.6363	0.6436	0.033*
C3	0.8801 (3)	0.7323 (2)	0.61767 (18)	0.0233 (6)
C8	0.9527 (3)	1.1675 (2)	0.61021 (18)	0.0253 (6)
C7	0.9411 (3)	1.0624 (2)	0.60741 (17)	0.0252 (6)
H7	1.0057	1.0245	0.5791	0.030*
C5	0.8133 (3)	0.9040 (2)	0.64572 (17)	0.0225 (6)
C4	0.9100 (3)	0.83539 (19)	0.61865 (16)	0.0223 (5)
H4	0.9948	0.8580	0.6011	0.027*
C1	0.6602 (3)	0.7753 (2)	0.67289 (19)	0.0281 (6)
H1	0.5752	0.7541	0.6914	0.034*
C10	0.7481 (3)	1.1682 (2)	0.69174 (19)	0.0290 (6)
H10	0.6821	1.2047	0.7202	0.035*
C17	1.1679 (4)	1.2577 (3)	0.6369 (2)	0.0507 (10)
H17A	1.2445	1.2919	0.6128	0.076*
H17B	1.1993	1.2006	0.6681	0.076*
H17C	1.1202	1.3032	0.6730	0.076*
C9	0.8536 (3)	1.2190 (2)	0.65550 (19)	0.0302 (7)
H9	0.8594	1.2888	0.6611	0.036*
C14	1.1222 (3)	0.6979 (3)	0.5698 (2)	0.0400 (8)
H14A	1.1817	0.6459	0.5498	0.060*
H14B	1.1580	0.7251	0.6205	0.060*
H14C	1.1155	0.7507	0.5292	0.060*
C13	0.9948 (3)	0.5689 (2)	0.6509 (2)	0.0397 (8)
H13A	1.0577	0.5189	0.6312	0.060*
H13B	0.9076	0.5381	0.6600	0.060*
H13C	1.0276	0.5969	0.7020	0.060*
C16	1.1495 (3)	1.1522 (3)	0.5092 (2)	0.0410 (8)
H16A	1.2235	1.1885	0.4844	0.062*
H16B	1.0890	1.1287	0.4667	0.062*
H16C	1.1845	1.0955	0.5396	0.062*
C12	0.9251 (4)	0.6105 (3)	0.5041 (2)	0.0440 (8)
H12A	0.9871	0.5607	0.4829	0.066*
H12B	0.9154	0.6641	0.4645	0.066*
H12C	0.8380	0.5798	0.5139	0.066*
C18	1.0207 (4)	1.3135 (3)	0.5182 (3)	0.0512 (10)
H18A	1.0965	1.3467	0.4923	0.077*
H18B	0.9755	1.3598	0.5547	0.077*
H18C	0.9581	1.2910	0.4764	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02290 (16)	0.02379 (17)	0.02875 (18)	0.00229 (14)	0.00540 (15)	−0.00019 (15)
O2	0.021	0.0581 (15)	0.0509 (13)	0.0047 (11)	−0.0042 (9)	0.0038 (14)
O1	0.0287 (10)	0.0327 (11)	0.0548 (15)	−0.0013 (9)	0.0091 (10)	0.0042 (9)
O4	0.0379 (11)	0.0321 (12)	0.0285 (11)	0.0100 (9)	0.0039 (10)	0.0011 (10)
N2	0.0264 (12)	0.0209 (12)	0.0256 (12)	0.0016 (10)	0.0028 (10)	0.0006 (10)
N4	0.0287 (13)	0.0328 (14)	0.0283 (13)	0.0002 (11)	0.0005 (11)	−0.0032 (11)
O5	0.033	0.034	0.038	0.0127 (10)	−0.0048 (9)	0.0036 (10)
N1	0.0248 (11)	0.0220 (13)	0.0260 (13)	−0.0020 (10)	0.0038 (10)	0.0000 (10)
N3	0.0263 (13)	0.0424 (16)	0.0455 (17)	0.0029 (11)	0.0057 (10)	−0.0132 (13)
O6	0.0737 (18)	0.0623 (17)	0.0313 (14)	0.0154 (14)	0.0022 (13)	−0.0100 (12)
C15	0.0309 (16)	0.0254 (15)	0.0361 (17)	−0.0065 (14)	−0.0001 (15)	0.0046 (12)
C6	0.0253 (13)	0.0220 (14)	0.0201 (13)	0.0005 (12)	0.0013 (11)	0.0000 (12)
C11	0.0330 (15)	0.0207 (15)	0.0299 (16)	0.0024 (13)	0.0008 (13)	−0.0045 (12)
O3	0.0275 (13)	0.0736 (19)	0.094 (2)	−0.0068 (12)	−0.0036 (13)	−0.0171 (17)
C2	0.0291 (14)	0.0201 (14)	0.0332 (17)	−0.0039 (12)	0.0012 (13)	−0.0010 (12)
C3	0.0286 (16)	0.0214 (14)	0.0200 (14)	0.0008 (11)	−0.0055 (12)	0.0007 (11)
C8	0.0287 (15)	0.0230 (15)	0.0242 (16)	−0.0037 (11)	−0.0047 (12)	0.0036 (12)
C7	0.0239 (15)	0.0255 (14)	0.0262 (15)	−0.0011 (11)	0.0027 (12)	−0.0024 (12)
C5	0.0246 (13)	0.0227 (15)	0.0202 (14)	−0.0013 (11)	0.0003 (12)	−0.0016 (12)
C4	0.0206 (12)	0.0243 (14)	0.0218 (13)	−0.0023 (12)	0.0018 (13)	−0.0016 (11)
C1	0.0258 (15)	0.0240 (15)	0.0344 (17)	−0.0039 (12)	0.0010 (13)	−0.0002 (13)
C10	0.0345 (15)	0.0232 (15)	0.0295 (16)	0.0059 (13)	0.0041 (13)	−0.0012 (12)
C17	0.045 (2)	0.056 (2)	0.051 (2)	−0.0223 (18)	−0.0037 (18)	−0.0033 (19)
C9	0.0381 (16)	0.0187 (15)	0.0339 (17)	−0.0004 (12)	−0.0017 (14)	−0.0016 (13)
C14	0.0333 (18)	0.0337 (18)	0.053 (2)	0.0072 (14)	0.0107 (15)	−0.0022 (16)
C13	0.0459 (19)	0.0285 (17)	0.045 (2)	0.0100 (15)	−0.0019 (16)	0.0064 (15)
C16	0.0365 (17)	0.0393 (19)	0.047 (2)	−0.0091 (15)	0.0115 (16)	0.0047 (16)
C12	0.051 (2)	0.043 (2)	0.0384 (18)	0.0096 (18)	−0.0011 (17)	−0.0151 (14)
C18	0.047 (2)	0.040 (2)	0.067 (3)	−0.0033 (17)	0.0112 (19)	0.0231 (19)

Geometric parameters (Å, º) top

Cu1—N1	1.965 (2)	C8—C9	1.396 (4)
Cu1—O4	1.976 (2)	C8—C7	1.398 (4)
Cu1—N2	1.980 (2)	C7—H7	0.9300
Cu1—O1	1.994 (2)	C5—C4	1.385 (4)
O2—N3	1.251 (4)	C4—H4	0.9300
O1—N3	1.290 (3)	C1—H1	0.9300
O4—N4	1.284 (3)	C10—C9	1.368 (4)
N2—C6	1.351 (3)	C10—H10	0.9300
N2—C10	1.350 (4)	C17—H17A	0.9600
N4—O6	1.223 (3)	C17—H17B	0.9600
N4—O5	1.243 (3)	C17—H17C	0.9600
N1—C1	1.340 (4)	C9—H9	0.9300
N1—C5	1.360 (4)	C14—H14A	0.9600
N3—O3	1.218 (3)	C14—H14B	0.9600
C15—C16	1.528 (4)	C14—H14C	0.9600
C15—C17	1.531 (5)	C13—H13A	0.9600
C15—C8	1.536 (4)	C13—H13B	0.9600
C15—C18	1.541 (4)	C13—H13C	0.9600
C6—C7	1.385 (4)	C16—H16A	0.9600
C6—C5	1.479 (4)	C16—H16B	0.9600
C11—C3	1.528 (4)	C16—H16C	0.9600
C11—C14	1.530 (4)	C12—H12A	0.9600
C11—C12	1.539 (4)	C12—H12B	0.9600
C11—C13	1.541 (4)	C12—H12C	0.9600
C2—C1	1.380 (4)	C18—H18A	0.9600
C2—C3	1.389 (4)	C18—H18B	0.9600
C2—H2	0.9300	C18—H18C	0.9600
C3—C4	1.396 (4)

N1—Cu1—O4	163.03 (9)	C4—C5—C6	124.1 (2)
N1—Cu1—N2	82.49 (9)	C5—C4—C3	120.0 (3)
O4—Cu1—N2	94.41 (9)	C5—C4—H4	120.0
N1—Cu1—O1	94.82 (9)	C3—C4—H4	120.0
O4—Cu1—O1	91.59 (9)	N1—C1—C2	122.4 (3)
N2—Cu1—O1	167.53 (10)	N1—C1—H1	118.8
N3—O1—Cu1	103.37 (17)	C2—C1—H1	118.8
N4—O4—Cu1	105.23 (16)	N2—C10—C9	122.2 (3)
C6—N2—C10	118.2 (2)	N2—C10—H10	118.9
C6—N2—Cu1	113.90 (18)	C9—C10—H10	118.9
C10—N2—Cu1	127.8 (2)	C15—C17—H17A	109.5
O6—N4—O5	123.3 (3)	C15—C17—H17B	109.5
O6—N4—O4	119.3 (2)	H17A—C17—H17B	109.5
O5—N4—O4	117.4 (2)	C15—C17—H17C	109.5
C1—N1—C5	118.0 (2)	H17A—C17—H17C	109.5
C1—N1—Cu1	127.3 (2)	H17B—C17—H17C	109.5
C5—N1—Cu1	114.09 (18)	C10—C9—C8	120.8 (3)
O3—N3—O2	124.3 (3)	C10—C9—H9	119.6
O3—N3—O1	119.2 (3)	C8—C9—H9	119.6
O2—N3—O1	116.5 (2)	C11—C14—H14A	109.5
C16—C15—C17	109.4 (3)	C11—C14—H14B	109.5
C16—C15—C8	111.8 (2)	H14A—C14—H14B	109.5
C17—C15—C8	107.1 (3)	C11—C14—H14C	109.5
C16—C15—C18	108.3 (3)	H14A—C14—H14C	109.5
C17—C15—C18	109.7 (3)	H14B—C14—H14C	109.5
C8—C15—C18	110.5 (3)	C11—C13—H13A	109.5
N2—C6—C7	121.9 (3)	C11—C13—H13B	109.5
N2—C6—C5	114.6 (2)	H13A—C13—H13B	109.5
C7—C6—C5	123.5 (3)	C11—C13—H13C	109.5
C3—C11—C14	112.4 (2)	H13A—C13—H13C	109.5
C3—C11—C12	108.1 (3)	H13B—C13—H13C	109.5
C14—C11—C12	108.7 (3)	C15—C16—H16A	109.5
C3—C11—C13	109.0 (2)	C15—C16—H16B	109.5
C14—C11—C13	108.4 (3)	H16A—C16—H16B	109.5
C12—C11—C13	110.3 (3)	C15—C16—H16C	109.5
C1—C2—C3	120.6 (3)	H16A—C16—H16C	109.5
C1—C2—H2	119.7	H16B—C16—H16C	109.5
C3—C2—H2	119.7	C11—C12—H12A	109.5
C2—C3—C4	116.9 (3)	C11—C12—H12B	109.5
C2—C3—C11	120.7 (2)	H12A—C12—H12B	109.5
C4—C3—C11	122.4 (3)	C11—C12—H12C	109.5
C9—C8—C7	116.5 (3)	H12A—C12—H12C	109.5
C9—C8—C15	122.4 (3)	H12B—C12—H12C	109.5
C7—C8—C15	121.0 (3)	C15—C18—H18A	109.5
C6—C7—C8	120.2 (3)	C15—C18—H18B	109.5
C6—C7—H7	119.9	H18A—C18—H18B	109.5
C8—C7—H7	119.9	C15—C18—H18C	109.5
N1—C5—C4	122.0 (3)	H18A—C18—H18C	109.5
N1—C5—C6	113.9 (2)	H18B—C18—H18C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O4ⁱ	0.93	2.46	3.124 (3)	129

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Cu(NO₃)₂(C₁₈H₂₄N₂)]
M_r	455.96
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	9.8265 (16), 13.247 (2), 16.138 (3)
V (Å³)	2100.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.08
Crystal size (mm)	0.27 × 0.25 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.759, 0.837
No. of measured, independent and observed [I > 2σ(I)] reflections	11065, 3642, 3450
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.074, 1.05
No. of reflections	3642
No. of parameters	258
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.81
Absolute structure	Flack (1983), 1522 Freidel pairs
Absolute structure parameter	0.012 (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
C1—H1···O4ⁱ	0.93	2.46	3.124 (3)	128.6

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

Acknowledgements

The authors gratefully acknowledge the Natural Science Foundation of China (No. 20767001), the International Collaborative Project of Guizhou Province, the Governor Foundation of Guizhou Province and the Natural Science Youth Foundation of Guizhou University (No. 2007–005) for financial support.

References

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