Bis(1H-benzotriazole-4-sulfonato-κ2N3,O)(2,2′-bipyridyl-κ2N,N′)cadmium

Zhu, X.-H.; Cheng, X.-C.

doi:10.1107/S160053681104596X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1699

https://doi.org/10.1107/S160053681104596X

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Bis(1H-benzotriazole-4-sulfonato-κ²N³,O)(2,2′-bipyridyl-κ²N,N′)cadmium

Xiao-Hong Zhu ^a ^* and Xiao-Chun Cheng ^a

^aFaculty of Life Science and Chemical Engineering, Huaiyin Institute of Technology, Huaian 223003, People's Republic of China
^*Correspondence e-mail: hgzhuxh@yeah.net

(Received 24 October 2011; accepted 1 November 2011; online 5 November 2011)

In the title complex, [Cd(C₆H₄N₃O₃S)₂(C₁₀H₈N₂)], the Cd²⁺ cation is located on a twofold rotation axis and is coordinated by two N and two O atoms from two symmetry-related benzotriazole-4-sulfonate anions and two N atoms from a 2,2-bipyridyl ligand, displaying a distorted CdN₄O₂ octahedral geometry. The crystal structure is stabilized by N—H⋯O and C—H⋯O hydrogen-bonding interactions.

Related literature

For a related structure, see: Xia et al. (2010 ).

Experimental

Crystal data

[Cd(C₆H₄N₃O₃S)₂(C₁₀H₈N₂)]
M_r = 664.95
Monoclinic, C 2/c
a = 8.148 (4) Å
b = 17.207 (7) Å
c = 17.720 (8) Å
β = 103.29 (1)°
V = 2417.8 (19) Å³
Z = 4
Mo Kα radiation
μ = 1.14 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.805, T_max = 0.805
8519 measured reflections
3009 independent reflections
2866 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.075
S = 1.05
3009 reflections
177 parameters
H-atom parameters constrained
Δρ_max = 0.82 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O2ⁱ	0.93	1.86	2.776 (3)	167
C3—H3⋯O3ⁱⁱ	0.93	2.55	3.255 (3)	133
C7—H7⋯O2ⁱⁱⁱ	0.93	2.56	3.204 (3)	127
Symmetry codes: (i) x+1, y, z; (ii) $[-x-{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ ; (iii) $[-x, y, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681104596X/pv2474sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104596X/pv2474Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681104596X/pv2474Isup3.cdx

checkCIF report

Comment top

Benzotriazole-4-sulfonic acid is often used as a ligand to synthesize complexes for its variable coordination modes. Herein, we report the crystal structure of title complex. The asymmetric unit consists of half of a cadmium ion, half of a 2,2-bipyridyl molecule, and a benzotriazole-4-sulfonate anion. The Cd ion is located on a two fold axis and coordinated by two N atoms from two different benzotriazole-4-sulfonate anions, two N atoms from 2,2-bipyridyl molecule, and two sulfonate O atoms from two different benzotriazole-4-sulfonate anions, displaying a distorted CdN₄O₂ octahedral geometry (Fig. 1). Both benzotriazole-4-sulfonate and 2,2-bipyridyl display bidentate chelating coordinating mode. In the crystal structure, there exist O—H···N and C—H···O hydrogen bonds (Table 1). Sulfonate O atoms as hydrogen bonding acceptor play a very important role in the formation of these hydrogen bonding interactions.

Related literature top

For a related structure, see: Xia et al. (2010).

Experimental top

A mixture of cadmium perchlorate hexahydrate (83.9 mg, 0.2 mmol), benzotriazole-4-sulfonic acid (39.8 mg, 0.2 mmol), 2,2-bipyridyl (31.2 mg, 0.2 mmol) and potassium hydroxide (11.2 mg, 0.2 mmol) in 12 ml H₂O was sealed in a 16 ml Teflon-lined stainless steel container and heated to 393 K for 3 days. After cooling to room temperature, colorless block crystals of the title complex were obtained.

Structure description top

For a related structure, see: Xia et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The coordination environment of Cd ion in the title complex with the ellipsoids drawn at the 30% probability level. The hydrogen atoms have been omitted for clarity. symmetry code: a: -x, y, -z+1/2.

Bis(1H-benzotriazole-4-sulfonato-κ²N³,O)(2,2'- bipyridyl-κ²N,N')cadmium top

Crystal data top

[Cd(C₆H₄N₃O₃S)₂(C₁₀H₈N₂)]	F(000) = 1328
M_r = 664.95	D_x = 1.827 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6866 reflections
a = 8.148 (4) Å	θ = 2.4–28.4°
b = 17.207 (7) Å	µ = 1.14 mm⁻¹
c = 17.720 (8) Å	T = 293 K
β = 103.29 (1)°	Block, colorless
V = 2417.8 (19) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3009 independent reflections
Radiation source: fine-focus sealed tube	2866 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
phi and ω scans	θ_max = 28.4°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
T_min = 0.805, T_max = 0.805	k = −22→22
8519 measured reflections	l = −23→17

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0361P)² + 1.8012P] where P = (F_o² + 2F_c²)/3
3009 reflections	(Δ/σ)_max < 0.001
177 parameters	Δρ_max = 0.82 e Å⁻³
0 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

[Cd(C₆H₄N₃O₃S)₂(C₁₀H₈N₂)]	V = 2417.8 (19) Å³
M_r = 664.95	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 8.148 (4) Å	µ = 1.14 mm⁻¹
b = 17.207 (7) Å	T = 293 K
c = 17.720 (8) Å	0.20 × 0.20 × 0.20 mm
β = 103.29 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3009 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2866 reflections with I > 2σ(I)
T_min = 0.805, T_max = 0.805	R_int = 0.073
8519 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.05	Δρ_max = 0.82 e Å⁻³
3009 reflections	Δρ_min = −0.64 e Å⁻³
177 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
C1	−0.0973 (2)	−0.10519 (11)	0.06169 (11)	0.0286 (3)
C2	−0.1066 (3)	−0.15816 (14)	0.00234 (12)	0.0388 (4)
H2	−0.2059	−0.1860	−0.0150	0.047*
C3	0.0298 (3)	−0.17160 (14)	−0.03310 (13)	0.0449 (5)
H3	0.0179	−0.2085	−0.0724	0.054*
C4	0.1784 (3)	−0.13203 (14)	−0.01131 (12)	0.0400 (5)
H4	0.2683	−0.1409	−0.0344	0.048*
C5	0.1872 (2)	−0.07701 (12)	0.04815 (11)	0.0297 (4)
C6	0.0555 (2)	−0.06363 (10)	0.08486 (10)	0.0252 (3)
C7	0.3344 (3)	0.12261 (16)	0.31089 (13)	0.0445 (5)
H7	0.3858	0.0742	0.3206	0.053*
C8	0.4326 (4)	0.18893 (19)	0.32763 (15)	0.0573 (7)
H8	0.5472	0.1855	0.3504	0.069*
C9	0.3560 (4)	0.26011 (18)	0.30959 (19)	0.0681 (9)
H9	0.4197	0.3055	0.3180	0.082*
C10	0.1860 (4)	0.26376 (15)	0.27930 (18)	0.0601 (7)
H10	0.1331	0.3116	0.2676	0.072*
C11	0.0927 (3)	0.19536 (12)	0.26615 (11)	0.0376 (4)
Cd1	0.0000	0.017130 (9)	0.2500	0.02575 (8)
N1	0.1089 (2)	−0.00941 (9)	0.14217 (10)	0.0281 (3)
N2	0.2645 (2)	0.01101 (11)	0.14125 (11)	0.0340 (4)
N3	0.3117 (2)	−0.02916 (11)	0.08527 (10)	0.0329 (3)
H3N	0.4172	−0.0247	0.0738	0.039*
N4	0.1685 (2)	0.12587 (10)	0.28136 (10)	0.0338 (3)
O1	−0.18547 (17)	−0.07919 (9)	0.19035 (8)	0.0335 (3)
O2	−0.3547 (2)	−0.02209 (10)	0.07349 (10)	0.0410 (4)
O3	−0.3666 (2)	−0.16108 (11)	0.09518 (10)	0.0492 (4)
S1	−0.26613 (5)	−0.09167 (3)	0.10818 (3)	0.02965 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0243 (8)	0.0342 (9)	0.0272 (8)	−0.0016 (7)	0.0055 (6)	0.0006 (7)
C2	0.0396 (11)	0.0449 (11)	0.0311 (9)	−0.0085 (9)	0.0066 (8)	−0.0059 (8)
C3	0.0592 (14)	0.0445 (12)	0.0351 (10)	−0.0033 (10)	0.0190 (10)	−0.0119 (9)
C4	0.0450 (11)	0.0463 (11)	0.0340 (10)	0.0051 (9)	0.0200 (9)	−0.0028 (9)
C5	0.0265 (8)	0.0363 (9)	0.0277 (8)	0.0035 (7)	0.0090 (7)	0.0043 (7)
C6	0.0231 (8)	0.0290 (8)	0.0239 (7)	0.0021 (6)	0.0062 (6)	0.0020 (6)
C7	0.0413 (11)	0.0528 (13)	0.0381 (10)	−0.0126 (10)	0.0065 (9)	0.0050 (9)
C8	0.0529 (15)	0.0773 (19)	0.0404 (12)	−0.0292 (14)	0.0078 (11)	−0.0097 (12)
C9	0.082 (2)	0.0547 (17)	0.0692 (18)	−0.0351 (15)	0.0195 (16)	−0.0240 (14)
C10	0.082 (2)	0.0328 (11)	0.0678 (17)	−0.0149 (12)	0.0225 (15)	−0.0123 (11)
C11	0.0582 (13)	0.0297 (9)	0.0283 (9)	−0.0072 (9)	0.0169 (8)	−0.0039 (7)
Cd1	0.02654 (11)	0.02444 (11)	0.02832 (11)	0.000	0.01050 (7)	0.000
N1	0.0234 (7)	0.0339 (8)	0.0281 (7)	−0.0031 (6)	0.0082 (6)	−0.0019 (6)
N2	0.0260 (8)	0.0460 (10)	0.0319 (8)	−0.0047 (6)	0.0104 (6)	−0.0015 (7)
N3	0.0233 (7)	0.0456 (9)	0.0318 (8)	−0.0004 (6)	0.0108 (6)	0.0007 (7)
N4	0.0384 (8)	0.0337 (8)	0.0301 (7)	−0.0077 (7)	0.0094 (6)	0.0010 (6)
O1	0.0291 (7)	0.0433 (8)	0.0283 (6)	−0.0103 (6)	0.0074 (5)	−0.0003 (5)
O2	0.0244 (7)	0.0578 (11)	0.0427 (8)	0.0073 (6)	0.0117 (6)	0.0099 (7)
O3	0.0450 (9)	0.0546 (10)	0.0499 (9)	−0.0275 (8)	0.0149 (7)	−0.0115 (8)
S1	0.0219 (2)	0.0385 (2)	0.0286 (2)	−0.00741 (16)	0.00572 (16)	−0.00111 (17)

Geometric parameters (Å, º) top

C1—C2	1.381 (3)	C9—H9	0.9300
C1—C6	1.412 (2)	C10—C11	1.391 (3)
C1—S1	1.774 (2)	C10—H10	0.9300
C2—C3	1.415 (3)	C11—N4	1.344 (3)
C2—H2	0.9300	C11—C11ⁱ	1.487 (5)
C3—C4	1.365 (3)	Cd1—N4	2.3114 (18)
C3—H3	0.9300	Cd1—N4ⁱ	2.3114 (18)
C4—C5	1.406 (3)	Cd1—O1	2.3267 (15)
C4—H4	0.9300	Cd1—O1ⁱ	2.3267 (15)
C5—N3	1.354 (3)	Cd1—N1	2.3293 (19)
C5—C6	1.397 (3)	Cd1—N1ⁱ	2.3293 (19)
C6—N1	1.374 (2)	N1—N2	1.319 (2)
C7—N4	1.334 (3)	N2—N3	1.336 (3)
C7—C8	1.386 (3)	N3—H3N	0.9310
C7—H7	0.9300	O1—S1	1.4690 (15)
C8—C9	1.378 (5)	O2—S1	1.4587 (17)
C8—H8	0.9300	O3—S1	1.4363 (16)
C9—C10	1.367 (5)

C2—C1—C6	116.48 (18)	N4—Cd1—N4ⁱ	71.91 (10)
C2—C1—S1	121.87 (15)	N4—Cd1—O1	166.80 (5)
C6—C1—S1	121.63 (14)	N4ⁱ—Cd1—O1	100.35 (7)
C1—C2—C3	122.3 (2)	N4—Cd1—O1ⁱ	100.35 (7)
C1—C2—H2	118.8	N4ⁱ—Cd1—O1ⁱ	166.80 (5)
C3—C2—H2	118.8	O1—Cd1—O1ⁱ	89.15 (8)
C4—C3—C2	121.9 (2)	N4—Cd1—N1	92.23 (6)
C4—C3—H3	119.0	N4ⁱ—Cd1—N1	106.18 (6)
C2—C3—H3	119.0	O1—Cd1—N1	79.50 (6)
C3—C4—C5	115.9 (2)	O1ⁱ—Cd1—N1	84.43 (6)
C3—C4—H4	122.0	N4—Cd1—N1ⁱ	106.18 (6)
C5—C4—H4	122.0	N4ⁱ—Cd1—N1ⁱ	92.23 (6)
N3—C5—C6	104.12 (17)	O1—Cd1—N1ⁱ	84.43 (6)
N3—C5—C4	132.63 (19)	O1ⁱ—Cd1—N1ⁱ	79.50 (6)
C6—C5—C4	123.20 (18)	N1—Cd1—N1ⁱ	157.38 (8)
N1—C6—C5	108.02 (16)	N2—N1—C6	108.28 (16)
N1—C6—C1	131.83 (17)	N2—N1—Cd1	120.41 (13)
C5—C6—C1	120.12 (17)	C6—N1—Cd1	128.60 (12)
N4—C7—C8	122.2 (3)	N1—N2—N3	108.25 (16)
N4—C7—H7	118.9	N2—N3—C5	111.32 (17)
C8—C7—H7	118.9	N2—N3—H3N	123.9
C9—C8—C7	118.3 (3)	C5—N3—H3N	124.8
C9—C8—H8	120.9	C7—N4—C11	119.6 (2)
C7—C8—H8	120.9	C7—N4—Cd1	123.54 (16)
C10—C9—C8	119.7 (2)	C11—N4—Cd1	116.87 (15)
C10—C9—H9	120.1	S1—O1—Cd1	130.56 (8)
C8—C9—H9	120.1	O3—S1—O2	113.99 (11)
C9—C10—C11	119.5 (3)	O3—S1—O1	112.90 (10)
C9—C10—H10	120.3	O2—S1—O1	111.29 (10)
C11—C10—H10	120.3	O3—S1—C1	106.89 (10)
N4—C11—C10	120.7 (2)	O2—S1—C1	105.86 (9)
N4—C11—C11ⁱ	117.13 (12)	O1—S1—C1	105.16 (9)
C10—C11—C11ⁱ	122.13 (17)

C6—C1—C2—C3	1.0 (3)	Cd1—N1—N2—N3	162.45 (12)
S1—C1—C2—C3	−177.47 (18)	N1—N2—N3—C5	0.0 (2)
C1—C2—C3—C4	−0.9 (4)	C6—C5—N3—N2	0.4 (2)
C2—C3—C4—C5	−0.3 (3)	C4—C5—N3—N2	−177.0 (2)
C3—C4—C5—N3	178.3 (2)	C8—C7—N4—C11	0.8 (3)
C3—C4—C5—C6	1.4 (3)	C8—C7—N4—Cd1	178.65 (18)
N3—C5—C6—N1	−0.6 (2)	C10—C11—N4—C7	1.4 (3)
C4—C5—C6—N1	177.08 (18)	C11ⁱ—C11—N4—C7	−179.5 (2)
N3—C5—C6—C1	−179.00 (16)	C10—C11—N4—Cd1	−176.55 (19)
C4—C5—C6—C1	−1.3 (3)	C11ⁱ—C11—N4—Cd1	2.5 (3)
C2—C1—C6—N1	−177.84 (19)	N4ⁱ—Cd1—N4—C7	−178.8 (2)
S1—C1—C6—N1	0.6 (3)	O1—Cd1—N4—C7	−123.2 (3)
C2—C1—C6—C5	0.1 (3)	O1ⁱ—Cd1—N4—C7	12.25 (18)
S1—C1—C6—C5	178.54 (14)	N1—Cd1—N4—C7	−72.49 (17)
N4—C7—C8—C9	−3.0 (4)	N1ⁱ—Cd1—N4—C7	94.20 (17)
C7—C8—C9—C10	2.9 (5)	N4ⁱ—Cd1—N4—C11	−0.92 (11)
C8—C9—C10—C11	−0.8 (5)	O1—Cd1—N4—C11	54.7 (3)
C9—C10—C11—N4	−1.4 (4)	O1ⁱ—Cd1—N4—C11	−169.89 (14)
C9—C10—C11—C11ⁱ	179.6 (3)	N1—Cd1—N4—C11	105.37 (15)
C5—C6—N1—N2	0.7 (2)	N1ⁱ—Cd1—N4—C11	−87.93 (15)
C1—C6—N1—N2	178.77 (19)	N4—Cd1—O1—S1	9.9 (3)
C5—C6—N1—Cd1	−160.36 (13)	N4ⁱ—Cd1—O1—S1	62.73 (12)
C1—C6—N1—Cd1	17.7 (3)	O1ⁱ—Cd1—O1—S1	−126.49 (14)
N4—Cd1—N1—N2	29.31 (15)	N1—Cd1—O1—S1	−41.99 (12)
N4ⁱ—Cd1—N1—N2	101.12 (15)	N1ⁱ—Cd1—O1—S1	153.99 (12)
O1—Cd1—N1—N2	−161.04 (16)	Cd1—O1—S1—O3	176.99 (11)
O1ⁱ—Cd1—N1—N2	−70.88 (15)	Cd1—O1—S1—O2	−53.35 (14)
N1ⁱ—Cd1—N1—N2	−115.61 (15)	Cd1—O1—S1—C1	60.81 (13)
N4—Cd1—N1—C6	−171.67 (16)	C2—C1—S1—O3	21.9 (2)
N4ⁱ—Cd1—N1—C6	−99.86 (16)	C6—C1—S1—O3	−156.48 (16)
O1—Cd1—N1—C6	−2.02 (15)	C2—C1—S1—O2	−99.96 (19)
O1ⁱ—Cd1—N1—C6	88.15 (16)	C6—C1—S1—O2	81.66 (17)
N1ⁱ—Cd1—N1—C6	43.42 (15)	C2—C1—S1—O1	142.14 (17)
C6—N1—N2—N3	−0.4 (2)	C6—C1—S1—O1	−36.25 (18)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2ⁱⁱ	0.93	1.86	2.776 (3)	167
C3—H3···O3ⁱⁱⁱ	0.93	2.55	3.255 (3)	133
C7—H7···O2ⁱ	0.93	2.56	3.204 (3)	127

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

Experimental details

Crystal data
Chemical formula	[Cd(C₆H₄N₃O₃S)₂(C₁₀H₈N₂)]
M_r	664.95
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	8.148 (4), 17.207 (7), 17.720 (8)
β (°)	103.29 (1)
V (Å³)	2417.8 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.14
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.805, 0.805
No. of measured, independent and observed [I > 2σ(I)] reflections	8519, 3009, 2866
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.075, 1.05
No. of reflections	3009
No. of parameters	177
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.64

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2ⁱ	0.93	1.86	2.776 (3)	167.0
C3—H3···O3ⁱⁱ	0.93	2.55	3.255 (3)	133.0
C7—H7···O2ⁱⁱⁱ	0.93	2.56	3.204 (3)	127.0

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

Acknowledgements

The authors gratefully acknowledge the Natural Science Foundation of Jiangsu Province of China (BK2008195) for financial support of this work.

References

Brandenburg, K. (2000). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xia, M.-Z., Lei, W., Wang, F.-Y., Jin, Z.-W. & Yang, T.-H. (2010). Asian J. Chem. 22, 3741–3744. CAS Google Scholar