1,4-Dihydro­quinoxaline-2,3-dione–5-nitro­isophthalic acid–water (1/1/1)

Wang, M.-F.

doi:10.1107/S1600536811020873

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1581

doi:10.1107/S1600536811020873

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1,4-Dihydroquinoxaline-2,3-dione–5-nitroisophthalic acid–water (1/1/1)

Ming-Feng Wang ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Jining University, 273155 Qufu, Shandong, People's Republic of China
^*Correspondence e-mail: mingfengwang_11@163.com

(Received 23 May 2011; accepted 31 May 2011; online 4 June 2011)

The asymmetric unit of the title compound, C₈H₆N₂O₂·C₈H₅NO₆·H₂O, contains molecules of 1,4-dihydroquinoxaline-2,3-dione, 5-nitroisophthalic acid and a solvent water. In the crystal structure, molecules are linked into a three-dimensional network by intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For applications of piperazine and its derivatives, see: Jian & Zhao (2004 ); Oxtoby et al. (2005 ). For uses of 5-nitroisophthalate and its derivatives, see: He et al. (2004 ); Wang et al. (2009 ); Xu et al. (2011 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₈H₆N₂O₂·C₈H₅NO₆·H₂O
M_r = 391.29
Triclinic, $[P \overline 1]$
a = 7.245 (2) Å
b = 8.686 (3) Å
c = 13.142 (4) Å
α = 93.938 (4)°
β = 95.619 (4)°
γ = 95.793 (4)°
V = 816.3 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 295 K
0.20 × 0.16 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.974, T_max = 0.987
4482 measured reflections
2857 independent reflections
2441 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.095
S = 1.03
2857 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O6ⁱ	0.86	2.40	2.9632 (18)	123
N2—H2⋯O9ⁱⁱ	0.86	2.33	3.0071 (17)	136
N1—H1⋯O1ⁱⁱⁱ	0.86	2.02	2.8723 (17)	173
O9—H9B⋯O2^iv	0.86	1.89	2.7456 (15)	171
O8—H8⋯O3^v	0.82	1.86	2.6381 (17)	159
O9—H9A⋯O1	0.86	1.97	2.8220 (15)	168
O4—H4A⋯O9	0.82	1.78	2.5962 (15)	173
Symmetry codes: (i) -x+2, -y+1, -z; (ii) x+1, y, z; (iii) -x+1, -y, -z+1; (iv) -x+1, -y+1, -z+1; (v) x, y+1, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005) and APEX2; data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020873/cv5099sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020873/cv5099Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020873/cv5099Isup3.cml

checkCIF report

Comment top

Piperazine and its derivatives have attracted a great interest due to their use as curatorial intermediate, bacteriophage and insectifuge (Jian & Zhao, 2004; Oxtoby et al., 2005). Coordination polymers of 5-nitroisophthalate and its derivatives have attracted interest because of their potential applications and intriguing architectures with new topologies (He et al., 2004; Wang et al., 2009; Xu et al., 2011). In this paper, we present the title compound (I).

In (I) (Fig. 1), the bond lengths and angles are normal (Allen et al., 1987). The asymmetric unit contains one molecule of 1,4-dihydro-2,3-quinoxalinedione, one molecule of 5-nitro-isophthalic acid and one crystalline water molecule.

The crystal packing is stabilized by intermolecular N—H···O and O—H···O hydrogen bonds (Table 1), which link the molecules into three-dimensional network.

Related literature top

For applications of piperazine and its derivatives, see: Jian & Zhao (2004); Oxtoby et al. (2005). For uses of 5-nitroisophthalate and its derivatives, see: He et al. (2004); Wang et al. (2009); Xu et al. (2011). For bond-length data, see: Allen et al. (1987).

Experimental top

A water solution (50 ml) of 1,4-Dihydro-2,3-quinoxalinedione (0.25 mmol) and 5-nitro-isophthalic acid (0.25 mmol) was heated at 333 K for 3 h. Then the mixture was cooled to room temperature. After two weeks orange crystals suitable for X-ray diffraction study were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The content of asymmetric unit of (I) showing the atomic labeling and 30% probability displacement ellipsoids.

1,4-Dihydroquinoxaline-2,3-dione–5-nitroisophthalic acid–water (1/1/1) top

Crystal data top

C₈H₆N₂O₂·C₈H₅NO₆·H₂O	Z = 2
M_r = 391.29	F(000) = 404
Triclinic, P1	D_x = 1.592 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.245 (2) Å	Cell parameters from 2442 reflections
b = 8.686 (3) Å	θ = 2.4–28.2°
c = 13.142 (4) Å	µ = 0.13 mm⁻¹
α = 93.938 (4)°	T = 295 K
β = 95.619 (4)°	Block, orange
γ = 95.793 (4)°	0.20 × 0.16 × 0.10 mm
V = 816.3 (4) Å³

Data collection top

Bruker APEXII CCD diffractometer	2857 independent reflections
Radiation source: fine-focus sealed tube	2441 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.974, T_max = 0.987	k = −9→10
4482 measured reflections	l = −15→15

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)] = 0.033	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0491P)² + 0.199P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2857 reflections	Δρ_max = 0.18 e Å⁻³
254 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.040 (3)

Crystal data top

C₈H₆N₂O₂·C₈H₅NO₆·H₂O	γ = 95.793 (4)°
M_r = 391.29	V = 816.3 (4) Å³
Triclinic, P1	Z = 2
a = 7.245 (2) Å	Mo Kα radiation
b = 8.686 (3) Å	µ = 0.13 mm⁻¹
c = 13.142 (4) Å	T = 295 K
α = 93.938 (4)°	0.20 × 0.16 × 0.10 mm
β = 95.619 (4)°

Data collection top

Bruker APEXII CCD diffractometer	2857 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2441 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.987	R_int = 0.017
4482 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.03	Δρ_max = 0.18 e Å⁻³
2857 reflections	Δρ_min = −0.19 e Å⁻³
254 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
N1	0.71730 (16)	0.01395 (14)	0.43192 (9)	0.0305 (3)
H1	0.6421	−0.0558	0.4543	0.037*
N2	0.96136 (17)	0.23142 (14)	0.36451 (9)	0.0322 (3)
H2	1.0403	0.2993	0.3431	0.039*
N3	0.86203 (18)	0.59454 (17)	−0.10289 (9)	0.0406 (3)
O1	0.53849 (14)	0.20004 (12)	0.47998 (8)	0.0398 (3)
O2	0.79757 (16)	0.42195 (12)	0.42271 (8)	0.0412 (3)
O3	0.54289 (17)	0.39843 (12)	0.20331 (9)	0.0467 (3)
O4	0.49185 (15)	0.61637 (12)	0.28917 (8)	0.0383 (3)
H4A	0.4479	0.5555	0.3277	0.058*
O5	0.85764 (19)	0.45403 (16)	−0.11072 (9)	0.0569 (4)
O6	0.9246 (2)	0.67836 (17)	−0.16454 (10)	0.0640 (4)
O7	0.7393 (2)	1.14774 (14)	0.02107 (10)	0.0599 (4)
O8	0.62819 (19)	1.11218 (13)	0.17111 (9)	0.0538 (3)
H8	0.6236	1.2062	0.1725	0.081*
O9	0.32657 (14)	0.43362 (12)	0.40853 (8)	0.0369 (3)
H9A	0.4013	0.3730	0.4352	0.055*
H9B	0.3007	0.4804	0.4643	0.055*
C1	0.67867 (19)	0.16099 (17)	0.44281 (10)	0.0293 (3)
C2	0.8180 (2)	0.28385 (17)	0.40886 (10)	0.0296 (3)
C3	0.9929 (2)	0.07624 (17)	0.35027 (10)	0.0299 (3)
C4	1.1426 (2)	0.0307 (2)	0.30139 (12)	0.0417 (4)
H4	1.2255	0.1047	0.2770	0.050*
C5	1.1677 (2)	−0.1238 (2)	0.28923 (13)	0.0481 (4)
H5	1.2657	−0.1545	0.2547	0.058*
C6	1.0477 (2)	−0.2347 (2)	0.32807 (12)	0.0436 (4)
H6	1.0674	−0.3389	0.3208	0.052*
C7	0.8999 (2)	−0.19105 (18)	0.37722 (11)	0.0346 (3)
H7	0.8201	−0.2652	0.4037	0.042*
C8	0.87052 (19)	−0.03525 (16)	0.38704 (10)	0.0280 (3)
C9	0.63865 (19)	0.64015 (17)	0.13886 (10)	0.0296 (3)
C10	0.7140 (2)	0.57178 (18)	0.05592 (10)	0.0324 (3)
H10	0.7161	0.4648	0.0475	0.039*
C11	0.7857 (2)	0.66751 (18)	−0.01360 (10)	0.0334 (3)
C12	0.7849 (2)	0.82652 (19)	−0.00467 (11)	0.0366 (4)
H12	0.8342	0.8876	−0.0530	0.044*
C13	0.7085 (2)	0.89318 (18)	0.07831 (11)	0.0334 (3)
C14	0.6363 (2)	0.79974 (17)	0.14970 (10)	0.0318 (3)
H14	0.5858	0.8448	0.2054	0.038*
C15	0.5552 (2)	0.53871 (17)	0.21328 (10)	0.0312 (3)
C16	0.6963 (2)	1.06385 (19)	0.08583 (12)	0.0394 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0280 (6)	0.0267 (6)	0.0384 (6)	−0.0004 (5)	0.0113 (5)	0.0073 (5)
N2	0.0322 (7)	0.0281 (7)	0.0385 (6)	−0.0004 (5)	0.0157 (5)	0.0061 (5)
N3	0.0386 (7)	0.0518 (9)	0.0324 (7)	0.0076 (7)	0.0079 (5)	0.0010 (6)
O1	0.0335 (6)	0.0351 (6)	0.0562 (7)	0.0079 (5)	0.0223 (5)	0.0112 (5)
O2	0.0493 (7)	0.0261 (6)	0.0520 (6)	0.0059 (5)	0.0213 (5)	0.0047 (5)
O3	0.0666 (8)	0.0256 (6)	0.0507 (7)	0.0053 (5)	0.0202 (6)	0.0022 (5)
O4	0.0488 (7)	0.0299 (6)	0.0394 (6)	0.0045 (5)	0.0195 (5)	0.0032 (4)
O5	0.0747 (9)	0.0491 (8)	0.0510 (7)	0.0162 (7)	0.0232 (6)	−0.0055 (6)
O6	0.0832 (10)	0.0687 (9)	0.0458 (7)	0.0048 (8)	0.0337 (7)	0.0107 (7)
O7	0.0803 (10)	0.0387 (7)	0.0648 (8)	0.0053 (7)	0.0193 (7)	0.0181 (6)
O8	0.0816 (9)	0.0283 (6)	0.0547 (7)	0.0125 (6)	0.0166 (6)	0.0037 (5)
O9	0.0390 (6)	0.0332 (6)	0.0405 (6)	0.0059 (5)	0.0122 (4)	0.0037 (4)
C1	0.0286 (7)	0.0300 (8)	0.0309 (7)	0.0042 (6)	0.0081 (6)	0.0049 (6)
C2	0.0324 (8)	0.0289 (8)	0.0288 (7)	0.0032 (6)	0.0089 (5)	0.0038 (6)
C3	0.0314 (8)	0.0296 (8)	0.0298 (7)	0.0044 (6)	0.0069 (6)	0.0026 (6)
C4	0.0372 (9)	0.0455 (10)	0.0463 (9)	0.0079 (7)	0.0177 (7)	0.0080 (7)
C5	0.0454 (10)	0.0500 (11)	0.0550 (10)	0.0196 (8)	0.0217 (8)	0.0039 (8)
C6	0.0488 (10)	0.0343 (9)	0.0491 (9)	0.0145 (8)	0.0049 (7)	−0.0012 (7)
C7	0.0359 (8)	0.0295 (8)	0.0381 (7)	0.0023 (6)	0.0026 (6)	0.0038 (6)
C8	0.0278 (7)	0.0294 (8)	0.0270 (6)	0.0033 (6)	0.0038 (5)	0.0015 (6)
C9	0.0293 (7)	0.0292 (8)	0.0304 (7)	0.0040 (6)	0.0036 (5)	0.0005 (6)
C10	0.0327 (8)	0.0307 (8)	0.0338 (7)	0.0047 (6)	0.0040 (6)	0.0001 (6)
C11	0.0315 (8)	0.0390 (9)	0.0299 (7)	0.0049 (7)	0.0055 (6)	−0.0008 (6)
C12	0.0348 (8)	0.0405 (9)	0.0352 (7)	0.0015 (7)	0.0057 (6)	0.0094 (7)
C13	0.0315 (8)	0.0317 (8)	0.0363 (7)	0.0023 (6)	0.0010 (6)	0.0036 (6)
C14	0.0325 (8)	0.0318 (8)	0.0313 (7)	0.0049 (6)	0.0047 (6)	0.0004 (6)
C15	0.0332 (8)	0.0281 (8)	0.0328 (7)	0.0056 (6)	0.0051 (6)	0.0003 (6)
C16	0.0402 (9)	0.0320 (9)	0.0455 (9)	0.0020 (7)	0.0018 (7)	0.0060 (7)

Geometric parameters (Å, º) top

N1—C1	1.3360 (18)	C3—C4	1.391 (2)
N1—C8	1.3972 (17)	C4—C5	1.373 (2)
N1—H1	0.8600	C4—H4	0.9300
N2—C2	1.3428 (17)	C5—C6	1.389 (3)
N2—C3	1.3928 (19)	C5—H5	0.9300
N2—H2	0.8600	C6—C7	1.376 (2)
N3—O5	1.2147 (19)	C6—H6	0.9300
N3—O6	1.2158 (18)	C7—C8	1.390 (2)
N3—C11	1.4764 (18)	C7—H7	0.9300
O1—C1	1.2365 (16)	C9—C14	1.386 (2)
O2—C2	1.2268 (18)	C9—C10	1.3900 (19)
O3—C15	1.2098 (18)	C9—C15	1.492 (2)
O4—C15	1.3114 (16)	C10—C11	1.381 (2)
O4—H4A	0.8200	C10—H10	0.9300
O7—C16	1.201 (2)	C11—C12	1.379 (2)
O8—C16	1.327 (2)	C12—C13	1.388 (2)
O8—H8	0.8200	C12—H12	0.9300
O9—H9A	0.8597	C13—C14	1.388 (2)
O9—H9B	0.8598	C13—C16	1.491 (2)
C1—C2	1.514 (2)	C14—H14	0.9300
C3—C8	1.390 (2)

C1—N1—C8	125.04 (12)	C6—C7—C8	119.52 (15)
C1—N1—H1	117.5	C6—C7—H7	120.2
C8—N1—H1	117.5	C8—C7—H7	120.2
C2—N2—C3	125.43 (12)	C3—C8—C7	120.28 (13)
C2—N2—H2	117.3	C3—C8—N1	118.07 (12)
C3—N2—H2	117.3	C7—C8—N1	121.64 (13)
O5—N3—O6	123.82 (13)	C14—C9—C10	120.07 (13)
O5—N3—C11	118.00 (13)	C14—C9—C15	120.96 (12)
O6—N3—C11	118.17 (14)	C10—C9—C15	118.95 (13)
C15—O4—H4A	109.5	C11—C10—C9	117.97 (14)
C16—O8—H8	109.5	C11—C10—H10	121.0
H9A—O9—H9B	98.3	C9—C10—H10	121.0
O1—C1—N1	123.40 (13)	C12—C11—C10	123.11 (13)
O1—C1—C2	119.59 (13)	C12—C11—N3	118.92 (13)
N1—C1—C2	117.01 (12)	C10—C11—N3	117.95 (14)
O2—C2—N2	123.62 (14)	C11—C12—C13	118.30 (14)
O2—C2—C1	120.46 (12)	C11—C12—H12	120.8
N2—C2—C1	115.92 (12)	C13—C12—H12	120.8
C8—C3—C4	119.61 (14)	C12—C13—C14	119.81 (14)
C8—C3—N2	118.35 (12)	C12—C13—C16	118.98 (14)
C4—C3—N2	122.04 (14)	C14—C13—C16	121.12 (13)
C5—C4—C3	119.81 (16)	C9—C14—C13	120.74 (13)
C5—C4—H4	120.1	C9—C14—H14	119.6
C3—C4—H4	120.1	C13—C14—H14	119.6
C4—C5—C6	120.48 (14)	O3—C15—O4	123.24 (14)
C4—C5—H5	119.8	O3—C15—C9	123.34 (13)
C6—C5—H5	119.8	O4—C15—C9	113.40 (12)
C7—C6—C5	120.25 (15)	O7—C16—O8	123.72 (15)
C7—C6—H6	119.9	O7—C16—C13	123.92 (15)
C5—C6—H6	119.9	O8—C16—C13	112.33 (13)

C8—N1—C1—O1	177.60 (13)	C15—C9—C10—C11	178.18 (12)
C8—N1—C1—C2	−3.47 (19)	C9—C10—C11—C12	−0.3 (2)
C3—N2—C2—O2	177.86 (13)	C9—C10—C11—N3	−178.69 (12)
C3—N2—C2—C1	−1.7 (2)	O5—N3—C11—C12	−178.32 (14)
O1—C1—C2—O2	3.7 (2)	O6—N3—C11—C12	1.3 (2)
N1—C1—C2—O2	−175.29 (13)	O5—N3—C11—C10	0.1 (2)
O1—C1—C2—N2	−176.70 (13)	O6—N3—C11—C10	179.69 (14)
N1—C1—C2—N2	4.33 (18)	C10—C11—C12—C13	0.1 (2)
C2—N2—C3—C8	−1.9 (2)	N3—C11—C12—C13	178.43 (13)
C2—N2—C3—C4	178.47 (14)	C11—C12—C13—C14	0.2 (2)
C8—C3—C4—C5	0.4 (2)	C11—C12—C13—C16	−176.43 (13)
N2—C3—C4—C5	180.00 (14)	C10—C9—C14—C13	0.1 (2)
C3—C4—C5—C6	−1.9 (3)	C15—C9—C14—C13	−177.81 (12)
C4—C5—C6—C7	1.4 (3)	C12—C13—C14—C9	−0.3 (2)
C5—C6—C7—C8	0.5 (2)	C16—C13—C14—C9	176.26 (13)
C4—C3—C8—C7	1.5 (2)	C14—C9—C15—O3	174.98 (14)
N2—C3—C8—C7	−178.08 (12)	C10—C9—C15—O3	−2.9 (2)
C4—C3—C8—N1	−177.39 (13)	C14—C9—C15—O4	−3.3 (2)
N2—C3—C8—N1	3.02 (19)	C10—C9—C15—O4	178.79 (12)
C6—C7—C8—C3	−2.0 (2)	C12—C13—C16—O7	4.3 (2)
C6—C7—C8—N1	176.89 (13)	C14—C13—C16—O7	−172.28 (16)
C1—N1—C8—C3	−0.2 (2)	C12—C13—C16—O8	−177.21 (14)
C1—N1—C8—C7	−179.10 (13)	C14—C13—C16—O8	6.2 (2)
C14—C9—C10—C11	0.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6ⁱ	0.86	2.40	2.9632 (18)	123
N2—H2···O9ⁱⁱ	0.86	2.33	3.0071 (17)	136
N1—H1···O1ⁱⁱⁱ	0.86	2.02	2.8723 (17)	173
O9—H9B···O2^iv	0.86	1.89	2.7456 (15)	171
O8—H8···O3^v	0.82	1.86	2.6381 (17)	159
O9—H9A···O1	0.86	1.97	2.8220 (15)	168
O4—H4A···O9	0.82	1.78	2.5962 (15)	173

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

Experimental details

Crystal data
Chemical formula	C₈H₆N₂O₂·C₈H₅NO₆·H₂O
M_r	391.29
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.245 (2), 8.686 (3), 13.142 (4)
α, β, γ (°)	93.938 (4), 95.619 (4), 95.793 (4)
V (Å³)	816.3 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.20 × 0.16 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.974, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	4482, 2857, 2441
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.095, 1.03
No. of reflections	2857
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6ⁱ	0.86	2.40	2.9632 (18)	123.2
N2—H2···O9ⁱⁱ	0.86	2.33	3.0071 (17)	135.9
N1—H1···O1ⁱⁱⁱ	0.86	2.02	2.8723 (17)	173.2
O9—H9B···O2^iv	0.86	1.89	2.7456 (15)	170.5
O8—H8···O3^v	0.82	1.86	2.6381 (17)	159.1
O9—H9A···O1	0.86	1.97	2.8220 (15)	168.3
O4—H4A···O9	0.82	1.78	2.5962 (15)	173.0

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
He, H.-Y., Zhou, Y.-L. & Zhu, L.-G. (2004). Acta Cryst. C60, m569–m571. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Jian, F. F. & Zhao, P. S. (2004). J. Mol. Struct. 705, 133–139. CrossRef CAS Google Scholar
Oxtoby, N. S., Blake, A. J., Champness, N. R. & Wilson, C. (2005). Chem. Eur. J. 11, 4643–4654. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, H.-D., Li, M.-M., He, H.-Y. & Jiang, F.-B. (2009). Acta Cryst. E65, m416. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xu, H.-B., Ma, S. & He, Y. (2011). Acta Cryst. E67, m326. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 7| July 2011| Page o1581

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