1-Hydroxy-4-aza-1-azoniabicyclo[2.2.2]octane picrate

Xiao, J.-M.

doi:10.1107/S1600536810023597

organic compounds

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Volume 66| Part 7| July 2010| Page o1764

doi:10.1107/S1600536810023597

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1-Hydroxy-4-aza-1-azoniabicyclo[2.2.2]octane picrate

Jing-Mei Xiao ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: xjm_cool@163.com

(Received 7 June 2010; accepted 18 June 2010; online 23 June 2010)

In the crystal structure of the title compound, C₆H₁₃N₂O⁺·C₆H₂N₃O₇⁻, the anions and cations are linked by O—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds into a three-dimensional network. The O atoms of a nitro group of the picrate anion are disordered over two positions of equal occupancy.

Related literature

For the dielectric properties of N-protonated compounds, see: Szafranski & Katrusiak (2008 ); Katrusiak & Szafranski (1999 ); Chen et al. (2009 ); Mihailovic et al. (1990 ).

Experimental

Crystal data

C₆H₁₃N₂O⁺·C₆H₂N₃O₇⁻
M_r = 357.29
Monoclinic, P 2₁ /c
a = 11.521 (2) Å
b = 19.230 (4) Å
c = 6.9921 (14) Å
β = 98.73 (3)°
V = 1531.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 293 K
0.3 × 0.25 × 0.2 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.176, T_max = 0.298
15623 measured reflections
3495 independent reflections
2111 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.176
S = 0.83
3495 reflections
249 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H1⋯O7	0.88 (3)	1.74 (4)	2.602 (3)	167 (3)
O8—H1⋯O6′	0.88 (3)	2.50 (4)	2.973 (15)	115 (3)
C7—H7B⋯O1	0.97	2.59	3.486 (4)	153
C9—H9A⋯O7	0.97	2.42	3.102 (3)	127
C5—H5⋯N5ⁱ	0.93	2.61	3.536 (3)	171
C11—H11A⋯O6′ⁱⁱ	0.97	2.54	3.342 (15)	139
C12—H12A⋯O5′ⁱⁱⁱ	0.97	2.31	3.176 (9)	149
C12—H12B⋯O5^iv	0.97	2.55	3.137 (7)	119
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z+1; (iii) -x+1, -y, -z+2; (iv) x+1, y, z.

Data collection: CrystalClear (Rigaku, 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810023597/rz2465sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023597/rz2465Isup2.hkl

checkCIF report

Comment top

The variable-temperature dielectric response, especially in relatively high frequency range, is very useful for searching phase transitions in which there is a dielectric anomaly at the transition temperature (Szafranski & Katrusiak, 2008; Katrusiak & Szafranski, 1999; Chen et al., 2009; Mihailovic et al., 1990). As part of a study on phase transitions of N-protonated compounds, the title compound has been synthesized and its dielectric properties measured. The title compound (m. p. = 405-410 K), however, showed no dielectric disuniformity in the range 93–395 K.

The asymmetric unit of the title compound (Fig. 1) contains one protonated triethylenediamine-N-oxide cation and one picrate anion. In the anion, the oxygen atoms of the nitro group including atom N3 are disordered over two positions with site occupancies of 0.5. The N1/O1/O2, N2/O3/O4, N3/O5/O6 and N3/O5'/O6' nitro groups are tilted with respect to the plane of the benzene ring by 31.6 (2), 4.8 (2), 23.8 (4) and 30.2 (6)° respectively. In the crystal structure (Fig. 2), anions and cations are linked by O—H···O, C—H···O and C—H···O hydrogen bonds (Table 1) into a three-dimensional network.

Related literature top

For the dielectric properties of N-protonated compounds, see: Szafranski & Katrusiak (2008); Katrusiak & Szafranski (1999); Chen et al. (2009); Mihailovic et al. (1990).

Experimental top

To a solution of triethylenediamine (50 mmol, 5.6 g) in benzene (500 ml) was added rapidly H₂0₂ (30%, 6.3 g) with stirring at room temperature. A precipitate formed at once. Water was removed from the reaction mixture by means of P₂O₅ drying in a vacuum oven at room temperature. The solid was washed with three 100 ml portions of ether. The crude product (10 mmol, 1.28 g) was dissolved in 10 ml methanol. Then 20 ml of an ethanol solution of picric acid (10 mmol, 2.29 g) was dropped slowly with stirring, and a yellow precipitate formed at once. The suspension was filtered and dissolved in water. After a few weeks, yellow block crystals were obtained by slow evaporation of the solvent.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. Dashed lines indicate hydrogen bonds.

1-Hydroxy-4-aza-1-azoniabicyclo[2.2.2]octane picrate top

Crystal data top

C₆H₁₃N₂O⁺·C₆H₂N₃O₇⁻	F(000) = 744
M_r = 357.29	D_x = 1.550 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5732 reflections
a = 11.521 (2) Å	θ = 3.8–27.5°
b = 19.230 (4) Å	µ = 0.13 mm⁻¹
c = 6.9921 (14) Å	T = 293 K
β = 98.73 (3)°	Prism, yellow
V = 1531.2 (5) Å³	0.3 × 0.25 × 0.2 mm
Z = 4

Data collection top

Rigaku Mercury2 diffractometer	3495 independent reflections
Radiation source: fine-focus sealed tube	2111 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
CCD Profile fitting scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −14→14
T_min = 0.176, T_max = 0.298	k = −24→24
15623 measured reflections	l = −9→9

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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.176	w = 1/[σ²(F_o²) + (0.0905P)² + 1.2925P] where P = (F_o² + 2F_c²)/3
S = 0.83	(Δ/σ)_max < 0.001
3495 reflections	Δρ_max = 0.18 e Å⁻³
249 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (2)

Crystal data top

C₆H₁₃N₂O⁺·C₆H₂N₃O₇⁻	V = 1531.2 (5) Å³
M_r = 357.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.521 (2) Å	µ = 0.13 mm⁻¹
b = 19.230 (4) Å	T = 293 K
c = 6.9921 (14) Å	0.3 × 0.25 × 0.2 mm
β = 98.73 (3)°

Data collection top

Rigaku Mercury2 diffractometer	3495 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2111 reflections with I > 2σ(I)
T_min = 0.176, T_max = 0.298	R_int = 0.064
15623 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 0.83	Δρ_max = 0.18 e Å⁻³
3495 reflections	Δρ_min = −0.17 e Å⁻³
249 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	Occ. (<1)
C1	0.30226 (19)	0.18175 (13)	0.6927 (3)	0.0374 (5)
C2	0.3052 (2)	0.25659 (13)	0.7118 (3)	0.0395 (6)
C3	0.2105 (2)	0.29629 (13)	0.7377 (3)	0.0413 (6)
H3	0.2160	0.3445	0.7403	0.050*
C4	0.1062 (2)	0.26361 (13)	0.7599 (3)	0.0392 (6)
C5	0.0965 (2)	0.19198 (14)	0.7588 (3)	0.0403 (6)
H5	0.0271	0.1706	0.7794	0.048*
C6	0.1917 (2)	0.15287 (13)	0.7266 (3)	0.0387 (5)
C7	0.6393 (2)	0.10824 (17)	0.9188 (4)	0.0584 (8)
H7A	0.6286	0.0821	1.0335	0.070*
H7B	0.5852	0.1472	0.9055	0.070*
C8	0.7660 (3)	0.1343 (2)	0.9351 (6)	0.0926 (13)
H8A	0.7658	0.1847	0.9319	0.111*
H8B	0.8091	0.1198	1.0587	0.111*
C9	0.6332 (2)	0.10287 (15)	0.5683 (4)	0.0510 (7)
H9A	0.5798	0.1421	0.5511	0.061*
H9B	0.6177	0.0734	0.4547	0.061*
C10	0.7612 (3)	0.1282 (2)	0.5971 (6)	0.0763 (10)
H10A	0.8001	0.1093	0.4951	0.092*
H10B	0.7619	0.1785	0.5862	0.092*
C11	0.7006 (2)	0.00311 (16)	0.7672 (5)	0.0630 (8)
H11A	0.6863	−0.0269	0.6545	0.076*
H11B	0.6907	−0.0240	0.8806	0.076*
C12	0.8254 (3)	0.03364 (19)	0.7890 (7)	0.0869 (12)
H12A	0.8693	0.0186	0.9114	0.104*
H12B	0.8649	0.0156	0.6864	0.104*
N1	0.41469 (19)	0.29372 (12)	0.6998 (3)	0.0490 (6)
N2	0.00623 (19)	0.30586 (13)	0.7894 (3)	0.0510 (6)
N3	0.1777 (2)	0.07762 (13)	0.7258 (4)	0.0558 (6)
N4	0.61729 (16)	0.06299 (10)	0.7448 (3)	0.0406 (5)
N5	0.8256 (2)	0.10837 (14)	0.7815 (4)	0.0641 (7)
O1	0.50786 (17)	0.26560 (12)	0.7614 (4)	0.0752 (7)
O2	0.40780 (19)	0.35263 (11)	0.6338 (3)	0.0678 (6)
O3	0.0149 (2)	0.36879 (12)	0.7812 (4)	0.0798 (7)
O4	−0.08245 (17)	0.27652 (12)	0.8233 (3)	0.0684 (6)
O5	0.0766 (4)	0.0514 (3)	0.6742 (11)	0.0852 (18)	0.50
O6	0.2617 (12)	0.0371 (7)	0.7403 (19)	0.066 (2)	0.50
O5'	0.1080 (6)	0.0591 (3)	0.8345 (12)	0.100 (2)	0.50
O6'	0.2427 (13)	0.0432 (7)	0.670 (2)	0.109 (5)	0.50
O7	0.38528 (15)	0.14793 (9)	0.6419 (3)	0.0523 (5)
O8	0.50320 (16)	0.03390 (10)	0.7282 (3)	0.0545 (5)
H1	0.457 (3)	0.0704 (19)	0.712 (5)	0.081 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0312 (12)	0.0454 (13)	0.0352 (12)	0.0040 (10)	0.0038 (9)	0.0017 (10)
C2	0.0347 (13)	0.0486 (14)	0.0352 (12)	−0.0032 (10)	0.0054 (10)	−0.0010 (10)
C3	0.0445 (14)	0.0450 (14)	0.0329 (12)	0.0040 (11)	0.0011 (10)	−0.0022 (10)
C4	0.0326 (12)	0.0512 (15)	0.0335 (12)	0.0090 (10)	0.0038 (9)	−0.0019 (10)
C5	0.0312 (12)	0.0570 (15)	0.0329 (12)	0.0011 (11)	0.0055 (9)	0.0020 (11)
C6	0.0351 (12)	0.0457 (14)	0.0356 (12)	0.0018 (10)	0.0068 (9)	0.0032 (10)
C7	0.0515 (17)	0.073 (2)	0.0507 (16)	−0.0038 (14)	0.0083 (13)	−0.0132 (14)
C8	0.061 (2)	0.121 (3)	0.095 (3)	−0.024 (2)	0.0081 (19)	−0.046 (2)
C9	0.0486 (15)	0.0561 (16)	0.0494 (15)	−0.0041 (12)	0.0104 (12)	0.0049 (13)
C10	0.0558 (19)	0.083 (2)	0.094 (3)	−0.0133 (17)	0.0259 (18)	0.020 (2)
C11	0.0495 (17)	0.0467 (16)	0.092 (2)	0.0080 (13)	0.0076 (15)	0.0077 (15)
C12	0.0439 (18)	0.071 (2)	0.144 (4)	0.0117 (16)	0.0082 (19)	0.012 (2)
N1	0.0454 (13)	0.0509 (14)	0.0521 (13)	−0.0051 (10)	0.0120 (10)	−0.0065 (11)
N2	0.0424 (13)	0.0605 (15)	0.0482 (13)	0.0137 (11)	0.0005 (10)	−0.0046 (11)
N3	0.0387 (12)	0.0511 (14)	0.0797 (17)	0.0007 (11)	0.0161 (12)	0.0093 (13)
N4	0.0302 (10)	0.0398 (11)	0.0521 (12)	−0.0012 (8)	0.0069 (8)	0.0013 (9)
N5	0.0356 (12)	0.0671 (17)	0.0889 (19)	−0.0035 (11)	0.0072 (12)	−0.0048 (14)
O1	0.0361 (11)	0.0724 (15)	0.115 (2)	−0.0041 (10)	0.0032 (11)	−0.0038 (13)
O2	0.0672 (14)	0.0541 (13)	0.0866 (16)	−0.0109 (10)	0.0263 (11)	0.0066 (11)
O3	0.0601 (14)	0.0561 (14)	0.123 (2)	0.0194 (11)	0.0128 (13)	−0.0058 (13)
O4	0.0412 (11)	0.0803 (15)	0.0881 (16)	0.0105 (10)	0.0235 (10)	−0.0057 (12)
O5	0.039 (3)	0.054 (3)	0.163 (6)	−0.011 (2)	0.018 (3)	−0.014 (4)
O6	0.046 (3)	0.047 (3)	0.104 (5)	0.004 (2)	0.008 (3)	0.015 (3)
O5'	0.080 (4)	0.072 (4)	0.160 (6)	0.005 (3)	0.059 (4)	0.040 (4)
O6'	0.086 (8)	0.051 (6)	0.204 (15)	−0.005 (5)	0.071 (9)	−0.045 (8)
O7	0.0383 (10)	0.0505 (11)	0.0712 (13)	0.0069 (8)	0.0187 (9)	0.0019 (9)
O8	0.0354 (10)	0.0458 (11)	0.0828 (14)	−0.0078 (8)	0.0108 (9)	0.0026 (10)

Geometric parameters (Å, º) top

C1—O7	1.252 (3)	C10—N5	1.438 (4)
C1—C6	1.442 (3)	C10—H10A	0.9700
C1—C2	1.445 (4)	C10—H10B	0.9700
C2—C3	1.365 (3)	C11—N4	1.492 (3)
C2—N1	1.463 (3)	C11—C12	1.540 (4)
C3—C4	1.386 (3)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—C5	1.382 (4)	C12—N5	1.438 (4)
C4—N2	1.450 (3)	C12—H12A	0.9700
C5—C6	1.376 (3)	C12—H12B	0.9700
C5—H5	0.9300	N1—O1	1.221 (3)
C6—N3	1.456 (3)	N1—O2	1.221 (3)
C7—N4	1.486 (3)	N2—O3	1.216 (3)
C7—C8	1.531 (4)	N2—O4	1.222 (3)
C7—H7A	0.9700	N3—O6'	1.114 (14)
C7—H7B	0.9700	N3—O6	1.235 (13)
C8—N5	1.447 (5)	N3—O5'	1.239 (6)
C8—H8A	0.9700	N3—O5	1.271 (5)
C8—H8B	0.9700	N4—O8	1.417 (2)
C9—N4	1.488 (3)	O5—O5'	1.134 (8)
C9—C10	1.537 (4)	O6—O6'	0.52 (2)
C9—H9A	0.9700	O8—H1	0.88 (3)
C9—H9B	0.9700

O7—C1—C6	125.4 (2)	N4—C11—C12	107.0 (2)
O7—C1—C2	122.4 (2)	N4—C11—H11A	110.3
C6—C1—C2	112.1 (2)	C12—C11—H11A	110.3
C3—C2—C1	124.1 (2)	N4—C11—H11B	110.3
C3—C2—N1	116.6 (2)	C12—C11—H11B	110.3
C1—C2—N1	119.3 (2)	H11A—C11—H11B	108.6
C2—C3—C4	119.0 (2)	N5—C12—C11	112.6 (3)
C2—C3—H3	120.5	N5—C12—H12A	109.1
C4—C3—H3	120.5	C11—C12—H12A	109.1
C5—C4—C3	121.5 (2)	N5—C12—H12B	109.1
C5—C4—N2	119.6 (2)	C11—C12—H12B	109.1
C3—C4—N2	118.9 (2)	H12A—C12—H12B	107.8
C6—C5—C4	118.7 (2)	O1—N1—O2	123.2 (2)
C6—C5—H5	120.7	O1—N1—C2	118.9 (2)
C4—C5—H5	120.7	O2—N1—C2	117.8 (2)
C5—C6—C1	124.2 (2)	O3—N2—O4	123.1 (2)
C5—C6—N3	117.0 (2)	O3—N2—C4	118.6 (2)
C1—C6—N3	118.8 (2)	O4—N2—C4	118.3 (2)
N4—C7—C8	107.1 (2)	O6'—N3—O5'	125.3 (8)
N4—C7—H7A	110.3	O6—N3—O5'	110.0 (7)
C8—C7—H7A	110.3	O6'—N3—O5	107.5 (9)
N4—C7—H7B	110.3	O6—N3—O5	116.5 (8)
C8—C7—H7B	110.3	O5'—N3—O5	53.7 (4)
H7A—C7—H7B	108.5	O6'—N3—C6	120.9 (8)
N5—C8—C7	112.7 (3)	O6—N3—C6	122.9 (7)
N5—C8—H8A	109.0	O5'—N3—C6	111.4 (4)
C7—C8—H8A	109.0	O5—N3—C6	119.4 (3)
N5—C8—H8B	109.0	O8—N4—C7	109.82 (19)
C7—C8—H8B	109.0	O8—N4—C9	111.43 (18)
H8A—C8—H8B	107.8	C7—N4—C9	110.5 (2)
N4—C9—C10	106.9 (2)	O8—N4—C11	106.12 (19)
N4—C9—H9A	110.3	C7—N4—C11	109.8 (2)
C10—C9—H9A	110.3	C9—N4—C11	109.0 (2)
N4—C9—H9B	110.3	C12—N5—C10	107.1 (3)
C10—C9—H9B	110.3	C12—N5—C8	108.3 (3)
H9A—C9—H9B	108.6	C10—N5—C8	109.6 (3)
N5—C10—C9	112.8 (2)	O5'—O5—N3	61.7 (4)
N5—C10—H10A	109.0	O6'—O6—N3	64 (3)
C9—C10—H10A	109.0	O5—O5'—N3	64.6 (4)
N5—C10—H10B	109.0	O6—O6'—N3	91 (3)
C9—C10—H10B	109.0	N4—O8—H1	103 (2)
H10A—C10—H10B	107.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H1···O7	0.88 (3)	1.74 (4)	2.602 (3)	167 (3)
O8—H1···O6′	0.88 (3)	2.50 (4)	2.973 (15)	115 (3)
C7—H7B···O1	0.97	2.59	3.486 (4)	153
C9—H9A···O7	0.97	2.42	3.102 (3)	127
C5—H5···N5ⁱ	0.93	2.61	3.536 (3)	171
C11—H11A···O6′ⁱⁱ	0.97	2.54	3.342 (15)	139
C12—H12A···O5′ⁱⁱⁱ	0.97	2.31	3.176 (9)	149
C12—H12B···O5^iv	0.97	2.55	3.137 (7)	119

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

Experimental details

Crystal data
Chemical formula	C₆H₁₃N₂O⁺·C₆H₂N₃O₇⁻
M_r	357.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.521 (2), 19.230 (4), 6.9921 (14)
β (°)	98.73 (3)
V (Å³)	1531.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.3 × 0.25 × 0.2

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.176, 0.298
No. of measured, independent and observed [I > 2σ(I)] reflections	15623, 3495, 2111
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.176, 0.83
No. of reflections	3495
No. of parameters	249
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.17

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H1···O7	0.88 (3)	1.74 (4)	2.602 (3)	167 (3)
O8—H1···O6'	0.88 (3)	2.50 (4)	2.973 (15)	115 (3)
C7—H7B···O1	0.97	2.59	3.486 (4)	153
C9—H9A···O7	0.97	2.42	3.102 (3)	127
C5—H5···N5ⁱ	0.93	2.61	3.536 (3)	171
C11—H11A···O6'ⁱⁱ	0.97	2.54	3.342 (15)	139
C12—H12A···O5'ⁱⁱⁱ	0.97	2.31	3.176 (9)	149
C12—H12B···O5^iv	0.97	2.55	3.137 (7)	119

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

Acknowledgements

This work was supported by a start-up grant from Southeast University.

References

Chen, L.-Z., Zhao, H., Ge, J.-Z., Wu, D.-H. & Xiong, R.-G. (2009). Cryst. Growth Des. 9, 3828–3831. Web of Science CSD CrossRef CAS Google Scholar
Katrusiak, A. & Szafranski, M. (1999). Phys. Rev. Lett. 82, 576–579. Web of Science CrossRef CAS Google Scholar
Mihailovic, P., Bassoul, P. & Simon, J. (1990). J. Phys. Chem. 94, 2815–2820. CSD CrossRef CAS Web of Science Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Szafranski, M. & Katrusiak, A. (2008). J. Phys. Chem. B, 112, 6779–6785. Web of Science CSD CrossRef PubMed CAS Google Scholar