N,N′-p-Phenyl­enediisonicotinamide monohydrate

Song, L.; Chai, W.; Lan, J.

doi:10.1107/S1600536809024684

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1749

doi:10.1107/S1600536809024684

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N,N′-p-Phenylenediisonicotinamide monohydrate

Li Song,^a ^* Wenxiang Chai ^b and Junwei Lan ^a

^aDepartment of Chemistry, Key Laboratory of Advanced Textile Materials and Manufacturing Technology of the Ministry of Education, Zhejiang Sci-Tech University, Hangzhou 310018, People's Republic of China, and ^bCollege of Materials Science and Engineering, China Jiliang University, Hangzhou 310018, People's Republic of China
^*Correspondence e-mail: songli@zstu.edu.cn

(Received 22 June 2009; accepted 26 June 2009; online 4 July 2009)

The organic molecule of the title compound, C₁₈H₁₄N₄O₂·H₂O, lies on a center of inversion located at the centre of the central phenylene ring. There are two half-molecules in the asymmetric unit. In the crystal, the molecules are linked through by N—H⋯O and O—H⋯N hydrogen bonds involving the water molecule, forming a layer structure. The layers interact by π–π interactions between the aromatic rings.

Related literature

For background to N,N′-p-phenylenediisonicotinamide complexes, see: Burchell et al. (2003 , 2004 ); Niu et al. (2004 ); Pansanel et al. (2006 ).

Experimental

Crystal data

C₁₈H₁₄N₄O₂·H₂O
M_r = 336.35
Triclinic, $[P \overline 1]$
a = 6.9936 (14) Å
b = 10.852 (2) Å
c = 11.285 (2) Å
α = 95.98 (3)°
β = 106.36 (3)°
γ = 94.68 (3)°
V = 811.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.32 × 0.21 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (CrystalStructure; Rigaku/MSC, 2004 ) T_min = 0.976, T_max = 0.987
7994 measured reflections
3671 independent reflections
1782 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.163
S = 1.10
3671 reflections
235 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3ⁱ	0.88	2.00	2.847 (3)	160
N4—H4A⋯O1	0.88	2.12	2.968 (3)	161
O3—H15⋯N1	0.94 (4)	1.92 (4)	2.845 (3)	168 (3)
O3—H16⋯N3ⁱⁱ	0.87 (4)	2.01 (4)	2.849 (3)	162 (4)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x-1, y-1, z-1.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024684/ng2603sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024684/ng2603Isup2.hkl

checkCIF report

Comment top

The incorporation of amide groups into organic ligands are of interests because of the existence of great and typical intermolecular hydrogen bondings. Furthermore, the bridging bis(pyridyl) ligands are good donors for building metal-organic frameworks (MOFs). As one example of bis(pyridyl) ligands with amide groups, N,N'-(biphenyl-4,4'-diyl)diisonicotinamide has been very less studied. Only a few examples built upon N,N'-(biphenyl-4,4'-diyl)diisonicotinamide and Cu(II), Hg(I) salts have been reported. However, the crystal structure of the ligand, N,N'-(biphenyl-4,4'-diyl)diisonicotinamide, has not been described in detail. Herein, we report the crystal structure and characterization of the title compound N,N'-(biphenyl-4,4'-diyl)diisonicotinamide.

The compound crystallizes in triclinic form in the space group P-1. As shown in Figure 1, the title compound, C18H14N4O2.H2O, contains an N,N'-(biphenyl-4,4'-diyl)diisonicotinamide molecule and a water solvent molecule. The bond lengths of the two independent parts of the C18H14N4O2 molecule display slight differences. The two C=O bonds of the amide groups are 1.223 (3) Å and 1.232 (3) Å long respectively. Individual molecules are connected through intermolecular N—H···O=C hydrogen bonds between amide groups The H(4 A)···O(1) distance is 2.12 Å and the N(4)···O(1) distance is 2.968 (3) Å. The N(4)—H(4 A)···O(1) angle is 161.3 °.

As shown in Figure 2, The molecules and the solvent water molecules are connected through the O—H···N hydrogen bonds between the water molecules and the pyridine groups or the amide groups (N(2)···O(3) = 2.847 (3) Å, O(3)···N(1) = 2.845 (3) Å, O(3)···N(3) = 2.849 (3) Å) to form a layer. The hydrogen bond geometry is listed in table 1. The layers pack via π-π interactions among the phenyl rings (Figure 3).

Related literature top

For background to N,N'-(biphenyl-4,4'-diyl)diisonicotinamide complexes, see: Burchell et al. (2003, 2004); Niu et al. (2004); Pansanel et al. (2006).

Experimental top

The synthesis of compound 1 was modified with reference to the literature methods (R. J. Puddephatt and H. W. Hou). Isonicotinic acid (4.924 g, 40.0 mmol) was refluxed in thionyl chloride (20 ml) for 4 h. Excess thionyl chloride was removed under vacuum leaving a colorless solid. The solid was suspended in tetrahydrofuran (80 ml) and then a solution of 1,4-phenylenediamine (1.622 g, 0.015 mol) in tetrahydrofuran (20 ml) was added. After 15 minutes of stirring, triethylamine (15.0 ml) was added. The solution was refluxed at 70 ?C for 6 h and cooled to room temperature. Removal of the excess solvents results in a great deal of light-yellow solid. A solution of K2CO3 (6.910 g, 50 mmol) in water (40 ml) was added into the solid. After 10 minutes of stirring, the white products were filtered, washed with water and ethanol. Yield: ca 82%. Well shaped colorless crystals were obtained by slow evaporation of DMF/THF solution. 1H NMR (400 MHz, DMSO): ¹H 7.781 (s, 4H), 7.879 (d, 4H), 8.786 (d, 4H), 10.527 (s, 2H). Anal. Calcd for C18H16N4O3: C 64.28, H 4.79, N 16.66. Found (%): C 64.12, H 4.91, N 16.78. IR (KBr pellet, cm^-1): 3329(s), 1647(s), 1611(m), 1593(sh), 1547(s), 1522(s), 1506(sh), 1485(w), 1413(m), 1321(m), 1276(w), 1219(w), 1066(w), 827(m), 756(w), 667(m).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Structure and labeling of compound 1, with displacement ellipsoids drawn at the 30% probability level and H atoms shown as small spheres of arbitrary radii.
	Fig. 2. The layer formed through the intermolecular hydrogen bonds.
	Fig. 3. The packing diagram viewed along the a-direction.

N,N'-p-Phenylenediisonicotinamide monohydrate top

Crystal data top

C₁₈H₁₄N₄O₂·H₂O	Z = 2
M_r = 336.35	F(000) = 352
Triclinic, P1	D_x = 1.376 Mg m⁻³
a = 6.9936 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.852 (2) Å	θ = 3.1–27.5°
c = 11.285 (2) Å	µ = 0.10 mm⁻¹
α = 95.98 (3)°	T = 296 K
β = 106.36 (3)°	Block, colorless
γ = 94.68 (3)°	0.32 × 0.21 × 0.13 mm
V = 811.8 (3) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	3671 independent reflections
Radiation source: fine-focus sealed tube	1782 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.039
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (CrystalStructure; Rigaku/MSC, 2004)	h = −9→8
T_min = 0.976, T_max = 0.987	k = −14→13
7994 measured reflections	l = −14→14

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.163	w = 1/[σ²(F_o²) + (0.0641P)² + 0.0836P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
3671 reflections	Δρ_max = 0.24 e Å⁻³
235 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (3)

Crystal data top

C₁₈H₁₄N₄O₂·H₂O	γ = 94.68 (3)°
M_r = 336.35	V = 811.8 (3) Å³
Triclinic, P1	Z = 2
a = 6.9936 (14) Å	Mo Kα radiation
b = 10.852 (2) Å	µ = 0.10 mm⁻¹
c = 11.285 (2) Å	T = 296 K
α = 95.98 (3)°	0.32 × 0.21 × 0.13 mm
β = 106.36 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3671 independent reflections
Absorption correction: multi-scan (CrystalStructure; Rigaku/MSC, 2004)	1782 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.987	R_int = 0.039
7994 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.24 e Å⁻³
3671 reflections	Δρ_min = −0.20 e Å⁻³
235 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	0.5143 (3)	0.75658 (16)	0.44339 (18)	0.0695 (6)
N1	0.3107 (4)	0.4128 (2)	0.0888 (2)	0.0784 (8)
C1	0.2062 (5)	0.4882 (3)	0.1391 (3)	0.0791 (9)
H1	0.0645	0.4691	0.1150	0.095*
O2	0.1628 (3)	0.77553 (17)	0.78063 (19)	0.0773 (6)
N2	0.7556 (3)	0.79239 (16)	0.34696 (18)	0.0511 (5)
H2A	0.7946	0.7654	0.2822	0.061*
C2	0.2908 (4)	0.5924 (2)	0.2241 (3)	0.0667 (7)
H2	0.2090	0.6436	0.2569	0.080*
O3	0.1253 (3)	0.2348 (2)	−0.12516 (19)	0.0774 (7)
N3	0.7983 (4)	1.0595 (2)	0.8737 (2)	0.0693 (7)
C3	0.4971 (4)	0.6211 (2)	0.2608 (2)	0.0507 (6)
N4	0.2782 (3)	0.70930 (17)	0.61858 (19)	0.0545 (5)
H4A	0.3716	0.7266	0.5825	0.065*
C4	0.6076 (4)	0.5436 (2)	0.2091 (2)	0.0557 (7)
H4	0.7495	0.5607	0.2313	0.067*
C5	0.5096 (5)	0.4414 (2)	0.1251 (3)	0.0680 (8)
H5	0.5877	0.3882	0.0911	0.082*
C6	0.5894 (4)	0.7301 (2)	0.3589 (2)	0.0522 (6)
C7	0.8750 (3)	0.89703 (19)	0.4275 (2)	0.0458 (6)
C8	0.8041 (4)	0.9772 (2)	0.5031 (2)	0.0558 (7)
H8	0.6698	0.9625	0.5058	0.067*
C9	1.0706 (4)	0.9205 (2)	0.4249 (2)	0.0556 (6)
H9	1.1201	0.8653	0.3725	0.067*
C10	0.6170 (4)	1.0792 (2)	0.8812 (3)	0.0671 (8)
H10	0.6015	1.1572	0.9219	0.081*
C11	0.4505 (4)	0.9927 (2)	0.8333 (2)	0.0582 (7)
H11	0.3243	1.0105	0.8426	0.070*
C12	0.4690 (4)	0.8799 (2)	0.7717 (2)	0.0517 (6)
C13	0.6558 (4)	0.8578 (2)	0.7638 (3)	0.0612 (7)
H13	0.6748	0.7810	0.7224	0.073*
C14	0.8155 (4)	0.9488 (3)	0.8169 (3)	0.0712 (8)
H14	0.9447	0.9316	0.8128	0.085*
C15	0.2873 (4)	0.7842 (2)	0.7236 (3)	0.0558 (6)
H15	0.173 (6)	0.289 (3)	−0.050 (4)	0.135 (14)*
C16	0.1331 (3)	0.6052 (2)	0.5602 (2)	0.0483 (6)
H16	0.026 (6)	0.191 (4)	−0.110 (4)	0.130 (14)*
C17	−0.0548 (4)	0.5897 (2)	0.5761 (2)	0.0569 (7)
H17	−0.0939	0.6510	0.6283	0.068*
C18	0.1870 (4)	0.5146 (2)	0.4836 (2)	0.0563 (7)
H18	0.3165	0.5244	0.4720	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0723 (13)	0.0736 (12)	0.0619 (12)	−0.0209 (9)	0.0365 (11)	−0.0191 (9)
N1	0.101 (2)	0.0679 (15)	0.0548 (16)	−0.0267 (14)	0.0189 (15)	−0.0060 (12)
C1	0.070 (2)	0.091 (2)	0.0567 (19)	−0.0302 (16)	0.0055 (16)	−0.0115 (16)
O2	0.0662 (13)	0.0869 (13)	0.0788 (15)	−0.0163 (10)	0.0395 (11)	−0.0206 (10)
N2	0.0530 (12)	0.0506 (11)	0.0433 (12)	−0.0092 (9)	0.0136 (9)	−0.0091 (8)
C2	0.0580 (17)	0.0734 (17)	0.0593 (18)	−0.0111 (13)	0.0120 (14)	−0.0043 (14)
O3	0.0852 (15)	0.0810 (13)	0.0592 (13)	−0.0318 (11)	0.0332 (12)	−0.0226 (10)
N3	0.0677 (16)	0.0679 (14)	0.0659 (16)	−0.0140 (11)	0.0201 (13)	−0.0044 (12)
C3	0.0562 (16)	0.0519 (13)	0.0396 (14)	−0.0060 (11)	0.0122 (12)	0.0012 (10)
N4	0.0539 (13)	0.0534 (11)	0.0528 (13)	−0.0095 (9)	0.0181 (10)	−0.0038 (9)
C4	0.0661 (17)	0.0486 (13)	0.0466 (15)	−0.0039 (11)	0.0126 (13)	−0.0002 (11)
C5	0.094 (2)	0.0542 (15)	0.0542 (17)	−0.0023 (14)	0.0240 (16)	0.0021 (12)
C6	0.0523 (15)	0.0524 (14)	0.0472 (15)	−0.0070 (11)	0.0130 (12)	0.0000 (11)
C7	0.0471 (14)	0.0471 (12)	0.0387 (13)	−0.0033 (10)	0.0110 (11)	−0.0035 (10)
C8	0.0473 (14)	0.0605 (14)	0.0546 (16)	−0.0063 (11)	0.0176 (12)	−0.0122 (12)
C9	0.0536 (15)	0.0536 (13)	0.0558 (16)	−0.0037 (11)	0.0198 (13)	−0.0126 (11)
C10	0.071 (2)	0.0572 (15)	0.0680 (19)	−0.0055 (13)	0.0215 (16)	−0.0059 (13)
C11	0.0575 (16)	0.0543 (14)	0.0620 (17)	0.0015 (11)	0.0206 (14)	−0.0006 (12)
C12	0.0530 (16)	0.0498 (13)	0.0489 (15)	−0.0001 (10)	0.0123 (12)	0.0032 (11)
C13	0.0532 (16)	0.0585 (15)	0.0693 (19)	−0.0023 (12)	0.0219 (14)	−0.0072 (13)
C14	0.0575 (18)	0.0773 (18)	0.075 (2)	−0.0038 (14)	0.0213 (15)	−0.0022 (15)
C15	0.0544 (16)	0.0547 (14)	0.0558 (17)	−0.0018 (11)	0.0171 (13)	−0.0006 (12)
C16	0.0444 (14)	0.0488 (13)	0.0488 (15)	−0.0018 (10)	0.0121 (11)	0.0030 (11)
C17	0.0500 (15)	0.0582 (14)	0.0600 (17)	−0.0005 (11)	0.0188 (13)	−0.0058 (12)
C18	0.0470 (15)	0.0604 (15)	0.0599 (17)	−0.0030 (11)	0.0194 (13)	−0.0031 (12)

Geometric parameters (Å, º) top

O1—C6	1.232 (3)	C5—H5	0.9500
N1—C1	1.327 (4)	C7—C8	1.372 (3)
N1—C5	1.335 (4)	C7—C9	1.380 (3)
C1—C2	1.375 (4)	C8—C9ⁱ	1.383 (3)
C1—H1	0.9500	C8—H8	0.9500
O2—C15	1.223 (3)	C9—C8ⁱ	1.383 (3)
N2—C6	1.343 (3)	C9—H9	0.9500
N2—C7	1.420 (3)	C10—C11	1.375 (3)
N2—H2A	0.8800	C10—H10	0.9500
C2—C3	1.383 (3)	C11—C12	1.377 (3)
C2—H2	0.9500	C11—H11	0.9500
O3—H15	0.94 (4)	C12—C13	1.373 (3)
O3—H16	0.87 (4)	C12—C15	1.506 (3)
N3—C10	1.327 (3)	C13—C14	1.378 (4)
N3—C14	1.333 (3)	C13—H13	0.9500
C3—C4	1.379 (3)	C14—H14	0.9500
C3—C6	1.498 (3)	C16—C17	1.375 (3)
N4—C15	1.348 (3)	C16—C18	1.387 (3)
N4—C16	1.422 (3)	C17—C18ⁱⁱ	1.382 (3)
N4—H4A	0.8800	C17—H17	0.9500
C4—C5	1.375 (3)	C18—C17ⁱⁱ	1.382 (3)
C4—H4	0.9500	C18—H18	0.9500

C1—N1—C5	116.7 (2)	C9ⁱ—C8—H8	120.2
N1—C1—C2	124.0 (3)	C7—C9—C8ⁱ	121.2 (2)
N1—C1—H1	118.0	C7—C9—H9	119.4
C2—C1—H1	118.0	C8ⁱ—C9—H9	119.4
C6—N2—C7	127.0 (2)	N3—C10—C11	123.5 (2)
C6—N2—H2A	116.5	N3—C10—H10	118.2
C7—N2—H2A	116.5	C11—C10—H10	118.2
C1—C2—C3	118.8 (3)	C10—C11—C12	119.2 (2)
C1—C2—H2	120.6	C10—C11—H11	120.4
C3—C2—H2	120.6	C12—C11—H11	120.4
H15—O3—H16	100 (3)	C13—C12—C11	118.0 (2)
C10—N3—C14	116.8 (2)	C13—C12—C15	123.2 (2)
C4—C3—C2	117.9 (2)	C11—C12—C15	118.7 (2)
C4—C3—C6	123.4 (2)	C12—C13—C14	119.0 (2)
C2—C3—C6	118.6 (2)	C12—C13—H13	120.5
C15—N4—C16	126.6 (2)	C14—C13—H13	120.5
C15—N4—H4A	116.7	N3—C14—C13	123.5 (3)
C16—N4—H4A	116.7	N3—C14—H14	118.3
C5—C4—C3	119.1 (3)	C13—C14—H14	118.3
C5—C4—H4	120.5	O2—C15—N4	124.2 (2)
C3—C4—H4	120.5	O2—C15—C12	120.4 (2)
N1—C5—C4	123.5 (3)	N4—C15—C12	115.4 (2)
N1—C5—H5	118.2	C17—C16—C18	118.9 (2)
C4—C5—H5	118.2	C17—C16—N4	123.8 (2)
O1—C6—N2	124.6 (2)	C18—C16—N4	117.3 (2)
O1—C6—C3	120.3 (2)	C16—C17—C18ⁱⁱ	120.2 (2)
N2—C6—C3	115.1 (2)	C16—C17—H17	119.9
C8—C7—C9	119.1 (2)	C18ⁱⁱ—C17—H17	119.9
C8—C7—N2	123.6 (2)	C17ⁱⁱ—C18—C16	120.8 (2)
C9—C7—N2	117.2 (2)	C17ⁱⁱ—C18—H18	119.6
C7—C8—C9ⁱ	119.6 (2)	C16—C18—H18	119.6
C7—C8—H8	120.2

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3ⁱⁱⁱ	0.88	2.00	2.847 (3)	160
N4—H4A···O1	0.88	2.12	2.968 (3)	161
O3—H15···N1	0.94 (4)	1.92 (4)	2.845 (3)	168 (3)
O3—H16···N3^iv	0.87 (4)	2.01 (4)	2.849 (3)	162 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄N₄O₂·H₂O
M_r	336.35
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.9936 (14), 10.852 (2), 11.285 (2)
α, β, γ (°)	95.98 (3), 106.36 (3), 94.68 (3)
V (Å³)	811.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.32 × 0.21 × 0.13

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (CrystalStructure; Rigaku/MSC, 2004)
T_min, T_max	0.976, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	7994, 3671, 1782
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.163, 1.10
No. of reflections	3671
No. of parameters	235
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.20

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), 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
N2—H2A···O3ⁱ	0.88	2.00	2.847 (3)	160.2
N4—H4A···O1	0.88	2.12	2.968 (3)	161.3
O3—H15···N1	0.94 (4)	1.92 (4)	2.845 (3)	168 (3)
O3—H16···N3ⁱⁱ	0.87 (4)	2.01 (4)	2.849 (3)	162 (4)

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

Acknowledgements

We are grateful for financial support from the Scientific Research Fund of Zhejiang Provincial Education Department (grant No. 20070358), the Analysis and Testing Foundation of Zhejiang Province (grant Nos. 2008F70034 and 2008F70053), the National Natural Science Foundation of China (grant No. 20803070) and the Young Scientists Fund of the Key Laboratory of Advanced Textile Materials and Manufacturing Technology of the Ministry of Education (grant No. 2007QN01).

References

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