2,3-Diamino­phenazine tetra­hydrate

Li, X.-F.; An, Y.; Yin, Y.-S.

doi:10.1107/S1600536808009598

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1000

doi:10.1107/S1600536808009598

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2,3-Diaminophenazine tetrahydrate

Xiao-Feng Li,^a ^* Yan An ^a and Yan-Sheng Yin ^a

^aInstitute of Marine Materials and Engineering, Shanghai Maritime University, Shanghai 200135, People's Republic of China
^*Correspondence e-mail: lxf_shmtu@yahoo.com.cn

(Received 2 March 2008; accepted 7 April 2008; online 7 May 2008)

The title compound, C₁₂H₁₀N₄·4H₂O, was obtained from a room-temperature solution of o-phenylenediamine and copper acetate. In the crystal structure, there are significant π–π stacking interactions, with a centroid–centroid separation of 3.575 (2) Å. In addition, intermolecular O—H⋯O, N—H⋯O, N—H⋯N and O—H⋯N hydrogen bonds link 2,3-diaminophenazine molecules and water molecules, forming a three-dimensional framework.

Related literature

For related literature, see: Brownstein & Enright (1995 ); Doyle et al. (2001 ); Chłopek et al. (2005 ).

Experimental

Crystal data

C₁₂H₁₀N₄·4H₂O
M_r = 282.30
Orthorhombic, P c a 2₁
a = 16.7593 (18) Å
b = 18.1200 (19) Å
c = 4.7834 (5) Å
V = 1452.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 (2) K
0.37 × 0.32 × 0.23 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.965, T_max = 0.977
7735 measured reflections
1608 independent reflections
1432 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.140
S = 1.14
1608 reflections
225 parameters
17 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯O2Wⁱ	0.895 (10)	2.218 (12)	3.105 (5)	171 (3)
N4—H4C⋯N4ⁱⁱ	0.90 (3)	2.58 (3)	3.198 (3)	126 (3)
N3—H3B⋯O1Wⁱⁱⁱ	0.906 (10)	2.165 (16)	3.048 (6)	165 (4)
N3—H3C⋯N3ⁱⁱ	0.895 (11)	2.33 (2)	3.122 (4)	147 (3)
O4W—H4WA⋯O4W^iv	0.855 (19)	2.017 (19)	2.871 (3)	176 (4)
O4W—H4WB⋯N2	0.867 (17)	1.924 (19)	2.787 (3)	173 (4)
O3W—H3WB⋯N1	0.872 (19)	1.96 (3)	2.801 (3)	161 (6)
O2W—H2WA⋯O4W^v	0.84 (2)	2.01 (2)	2.843 (4)	178 (5)
O1W—H1WA⋯O1W^vi	0.84 (6)	2.15 (6)	2.860 (7)	142 (6)
O2W—H2WB⋯O2W^vii	0.87 (4)	1.97 (4)	2.812 (5)	161 (3)
O1W—H1WB⋯O3W	0.85 (3)	2.09 (3)	2.882 (6)	155 (5)
Symmetry codes: (i) x, y, z-1; (ii) $[-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[-x+1, -y, z-{\script{1\over 2}}]$ ; (v) $[-x+1, -y, z+{\script{1\over 2}}]$ ; (vi) $[-x+{\script{3\over 2}}, y, z+{\script{1\over 2}}]$ ; (vii) $[-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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/S1600536808009598/lh2601sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009598/lh2601Isup2.hkl

checkCIF report

Comment top

The crystal structures of phenazinediamine (Doyle, et al., 2001) and examples of its derivatives (Brownstein, et al., 1995; Krzysztof, et al., 2005) have been published. As part of our studies of these types of compounds we report here the crystal structure of the title compound (I) which was synthesized at room temperature using o-Phenylenediamine and copper acetate.

In compound (I), the asymmetric unit contains a 2,3-Diamino-phenazine molecule and four water molecules (Fig. 1). In the crystal structure, 2,3-Diamino-phenazine molecules related by unit cell translations along the c axis form moderately strong π···π stacking interactions (Cg1···.Cg2(x, y, -1 + z) and Cg1···Cg3(x, y, 1 + z) = 3.575 (2) Å, where Cg1, Cg2 and Cg3 are the centroids defined by ring atoms N1/N2/C1/C6/C9/C10, C1—C6 and C7—C12, respectively). In addition, water molecules and 2,3-Diamino-phenazine molecules are linked by O—H···N, O—H···O, N—H···N and H—H···O hydrogen bonds to form a three-dimensional network (Table 1 & Fig.2).

Related literature top

For related literature, see: Brownstein & Enright (1995); Doyle et al. (2001); Krzysztof et al. (2005).

Experimental top

A mixture of o-Phenylenediamine(0.5 mmol, 0.054 g), Cu(CH₃COO)₂ (0.5 mmol,0.099 g), NaOH (1 mmol, 0.04 g), and water (10 ml) was placed in a 20 ml vial, stirring in air for 1 h. It was then sealed for 1 week and the resulting black block-shaped single crystals were collected. Yield: 67%. C&H analysis for C₁₂H₁₈N₄O₄ (found/calc): C, 51.03(51.06), H, 6.39(6.43).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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. The asymmetric unit of (I).
	Fig. 2. Part of the crystal structure viewed along the c-axis. Dashed lines are drawn between the donor and acceptor atoms of the hydrogen bonds but H atoms are not showm.

2,3-Diaminophenazine tetrahydrate top

Crystal data top

C₁₂H₁₀N₄·4H₂O	F(000) = 600
M_r = 282.30	D_x = 1.291 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3569 reflections
a = 16.7593 (18) Å	θ = 2.7–24.3°
b = 18.1200 (19) Å	µ = 0.10 mm⁻¹
c = 4.7834 (5) Å	T = 293 K
V = 1452.6 (3) Å³	Block, black
Z = 4	0.37 × 0.32 × 0.23 mm

Data collection top

Bruker SMART APEX area-detector diffractometer	1608 independent reflections
Radiation source: fine-focus sealed tube	1432 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→18
T_min = 0.965, T_max = 0.977	k = −19→22
7735 measured reflections	l = −5→5

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.0963P)²] where P = (F_o² + 2F_c²)/3
1608 reflections	(Δ/σ)_max < 0.001
225 parameters	Δρ_max = 0.29 e Å⁻³
17 restraints	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₁₂H₁₀N₄·4H₂O	V = 1452.6 (3) Å³
M_r = 282.30	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 16.7593 (18) Å	µ = 0.10 mm⁻¹
b = 18.1200 (19) Å	T = 293 K
c = 4.7834 (5) Å	0.37 × 0.32 × 0.23 mm

Data collection top

Bruker SMART APEX area-detector diffractometer	1608 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1432 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.977	R_int = 0.022
7735 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	17 restraints
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.29 e Å⁻³
1608 reflections	Δρ_min = −0.12 e Å⁻³
225 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	0.51508 (13)	0.31719 (12)	0.3965 (5)	0.0417 (6)
N2	0.51933 (12)	0.16406 (12)	0.2821 (6)	0.0410 (5)
C10	0.46946 (14)	0.20894 (15)	0.1460 (6)	0.0393 (6)
C11	0.41763 (15)	0.18021 (16)	−0.0623 (7)	0.0443 (7)
H11A	0.4184	0.1299	−0.1008	0.053*
C1	0.56542 (15)	0.27142 (16)	0.5338 (6)	0.0418 (7)
C12	0.36660 (15)	0.22488 (17)	−0.2076 (6)	0.0445 (7)
C8	0.41408 (16)	0.33188 (16)	0.0507 (7)	0.0456 (7)
H8A	0.4123	0.3823	0.0873	0.055*
C9	0.46739 (15)	0.28738 (15)	0.2042 (6)	0.0394 (6)
N4	0.31334 (15)	0.19700 (17)	−0.3960 (7)	0.0603 (8)
H4B	0.3134 (18)	0.1476 (6)	−0.403 (10)	0.072*
H4C	0.2916 (19)	0.2287 (16)	−0.520 (7)	0.072*
N3	0.30987 (17)	0.34664 (19)	−0.2858 (6)	0.0630 (8)
H3B	0.315 (2)	0.3961 (7)	−0.263 (12)	0.076*
H3C	0.2912 (19)	0.333 (2)	−0.454 (4)	0.076*
C5	0.62032 (15)	0.14891 (17)	0.6301 (7)	0.0498 (7)
H5A	0.6222	0.0985	0.5942	0.060*
C6	0.56701 (14)	0.19474 (15)	0.4760 (6)	0.0401 (6)
C2	0.61674 (16)	0.30014 (19)	0.7428 (7)	0.0512 (8)
H2A	0.6163	0.3504	0.7828	0.061*
C7	0.36499 (15)	0.30342 (16)	−0.1501 (6)	0.0446 (7)
C4	0.66820 (16)	0.1785 (2)	0.8286 (7)	0.0561 (8)
H4A	0.7025	0.1480	0.9289	0.067*
C3	0.66680 (18)	0.25428 (18)	0.8851 (7)	0.0576 (9)
H3A	0.7004	0.2736	1.0213	0.069*
O4W	0.54392 (14)	0.01642 (12)	0.1437 (6)	0.0592 (6)
O3W	0.53446 (19)	0.47020 (15)	0.4439 (8)	0.0798 (8)
O2W	0.29410 (18)	0.02670 (19)	0.5763 (7)	0.0818 (8)
O1W	0.7032 (3)	0.4897 (3)	0.3542 (10)	0.1042 (11)
H4WB	0.541 (2)	0.0631 (11)	0.182 (8)	0.088 (14)*
H3WB	0.535 (3)	0.4238 (14)	0.396 (16)	0.16 (3)*
H4WA	0.516 (2)	0.0085 (18)	−0.004 (7)	0.070 (12)*
H3WA	0.4832 (14)	0.481 (2)	0.455 (16)	0.14 (2)*
H2WA	0.3416 (11)	0.014 (2)	0.601 (11)	0.102 (16)*
H1WA	0.723 (3)	0.469 (4)	0.495 (12)	0.22 (4)*
H2WB	0.266 (2)	0.016 (2)	0.724 (8)	0.093 (16)*
H1WB	0.6547 (14)	0.478 (2)	0.330 (13)	0.11 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0396 (11)	0.0510 (12)	0.0344 (13)	−0.0021 (9)	0.0026 (10)	−0.0015 (11)
N2	0.0359 (11)	0.0526 (12)	0.0346 (12)	0.0009 (9)	0.0026 (11)	−0.0002 (11)
C10	0.0319 (12)	0.0550 (14)	0.0311 (14)	−0.0024 (10)	0.0056 (12)	0.0001 (12)
C11	0.0373 (13)	0.0571 (15)	0.0386 (15)	−0.0018 (12)	−0.0006 (13)	−0.0059 (13)
C1	0.0337 (13)	0.0606 (16)	0.0309 (15)	−0.0032 (11)	0.0033 (11)	0.0012 (12)
C12	0.0302 (13)	0.0741 (18)	0.0293 (14)	−0.0081 (12)	0.0057 (11)	−0.0011 (14)
C8	0.0444 (14)	0.0551 (14)	0.0375 (16)	0.0061 (12)	0.0035 (13)	0.0010 (13)
C9	0.0361 (12)	0.0509 (14)	0.0313 (16)	0.0018 (11)	0.0035 (11)	−0.0008 (12)
N4	0.0465 (14)	0.092 (2)	0.0428 (16)	−0.0086 (13)	−0.0108 (13)	−0.0011 (17)
N3	0.0539 (15)	0.089 (2)	0.0463 (17)	0.0191 (14)	−0.0071 (14)	0.0025 (15)
C5	0.0394 (13)	0.0697 (17)	0.0401 (17)	0.0079 (12)	0.0028 (13)	0.0071 (16)
C6	0.0303 (12)	0.0586 (15)	0.0315 (15)	−0.0004 (10)	0.0021 (12)	0.0022 (13)
C2	0.0423 (15)	0.0733 (18)	0.0379 (17)	−0.0112 (13)	0.0007 (13)	−0.0048 (16)
C7	0.0357 (13)	0.0699 (18)	0.0282 (15)	0.0063 (12)	0.0034 (12)	0.0024 (13)
C4	0.0358 (14)	0.090 (2)	0.0421 (18)	0.0057 (15)	−0.0020 (13)	0.0131 (17)
C3	0.0379 (15)	0.098 (3)	0.0366 (16)	−0.0096 (15)	−0.0058 (14)	0.0019 (17)
O4W	0.0671 (14)	0.0536 (12)	0.0569 (15)	0.0009 (10)	−0.0081 (13)	0.0014 (12)
O3W	0.103 (2)	0.0588 (14)	0.078 (2)	−0.0099 (13)	−0.003 (2)	−0.0042 (14)
O2W	0.0642 (17)	0.118 (2)	0.0636 (18)	0.0089 (16)	−0.0007 (16)	0.0027 (17)
O1W	0.097 (2)	0.123 (3)	0.092 (3)	−0.006 (2)	0.007 (2)	0.011 (2)

Geometric parameters (Å, º) top

N1—C9	1.333 (3)	N3—H3B	0.906 (10)
N1—C1	1.353 (3)	N3—H3C	0.895 (11)
N2—C10	1.335 (3)	C5—C4	1.353 (5)
N2—C6	1.345 (4)	C5—C6	1.425 (4)
C10—C11	1.421 (4)	C5—H5A	0.9300
C10—C9	1.449 (4)	C2—C3	1.363 (4)
C11—C12	1.367 (4)	C2—H2A	0.9300
C11—H11A	0.9300	C4—C3	1.400 (4)
C1—C6	1.417 (4)	C4—H4A	0.9300
C1—C2	1.417 (4)	C3—H3A	0.9300
C12—N4	1.366 (4)	O4W—H4WB	0.867 (17)
C12—C7	1.450 (4)	O4W—H4WA	0.855 (19)
C8—C7	1.366 (4)	O3W—H3WB	0.872 (19)
C8—C9	1.410 (4)	O3W—H3WA	0.883 (19)
C8—H8A	0.9300	O2W—H2WA	0.837 (19)
N4—H4B	0.895 (10)	O2W—H2WB	0.87 (4)
N4—H4C	0.90 (3)	O1W—H1WA	0.84 (6)
N3—C7	1.374 (4)	O1W—H1WB	0.849 (18)

C9—N1—C1	117.4 (2)	C7—N3—H3C	120 (3)
C10—N2—C6	117.2 (2)	H3B—N3—H3C	114 (4)
N2—C10—C11	120.1 (2)	C4—C5—C6	120.3 (3)
N2—C10—C9	121.2 (2)	C4—C5—H5A	119.9
C11—C10—C9	118.7 (2)	C6—C5—H5A	119.9
C12—C11—C10	121.5 (3)	N2—C6—C1	121.9 (2)
C12—C11—H11A	119.3	N2—C6—C5	119.2 (3)
C10—C11—H11A	119.3	C1—C6—C5	118.8 (2)
N1—C1—C6	121.2 (2)	C3—C2—C1	120.1 (3)
N1—C1—C2	119.7 (3)	C3—C2—H2A	119.9
C6—C1—C2	119.1 (3)	C1—C2—H2A	119.9
N4—C12—C11	121.7 (3)	C8—C7—N3	121.5 (3)
N4—C12—C7	118.4 (3)	C8—C7—C12	119.5 (3)
C11—C12—C7	119.8 (3)	N3—C7—C12	118.9 (3)
C7—C8—C9	122.2 (3)	C5—C4—C3	120.9 (3)
C7—C8—H8A	118.9	C5—C4—H4A	119.6
C9—C8—H8A	118.9	C3—C4—H4A	119.6
N1—C9—C8	120.5 (3)	C2—C3—C4	120.8 (3)
N1—C9—C10	121.1 (2)	C2—C3—H3A	119.6
C8—C9—C10	118.4 (2)	C4—C3—H3A	119.6
C12—N4—H4B	113 (3)	H4WB—O4W—H4WA	108 (2)
C12—N4—H4C	118 (2)	H3WB—O3W—H3WA	105 (2)
H4B—N4—H4C	128 (4)	H2WA—O2W—H2WB	109 (2)
C7—N3—H3B	117 (3)	H1WA—O1W—H1WB	112 (3)

C6—N2—C10—C11	179.8 (2)	N1—C1—C6—N2	0.5 (4)
C6—N2—C10—C9	0.4 (4)	C2—C1—C6—N2	179.4 (3)
N2—C10—C11—C12	−179.2 (2)	N1—C1—C6—C5	−179.0 (3)
C9—C10—C11—C12	0.2 (4)	C2—C1—C6—C5	0.0 (4)
C9—N1—C1—C6	−0.3 (4)	C4—C5—C6—N2	−179.2 (3)
C9—N1—C1—C2	−179.2 (2)	C4—C5—C6—C1	0.2 (4)
C10—C11—C12—N4	−176.0 (3)	N1—C1—C2—C3	179.0 (3)
C10—C11—C12—C7	0.2 (4)	C6—C1—C2—C3	0.0 (4)
C1—N1—C9—C8	−179.3 (2)	C9—C8—C7—N3	175.9 (3)
C1—N1—C9—C10	0.2 (4)	C9—C8—C7—C12	0.6 (4)
C7—C8—C9—N1	179.2 (2)	N4—C12—C7—C8	175.8 (3)
C7—C8—C9—C10	−0.2 (4)	C11—C12—C7—C8	−0.6 (4)
N2—C10—C9—N1	−0.3 (3)	N4—C12—C7—N3	0.4 (4)
C11—C10—C9—N1	−179.6 (3)	C11—C12—C7—N3	−176.0 (3)
N2—C10—C9—C8	179.2 (3)	C6—C5—C4—C3	−0.5 (4)
C11—C10—C9—C8	−0.2 (3)	C1—C2—C3—C4	−0.3 (5)
C10—N2—C6—C1	−0.5 (4)	C5—C4—C3—C2	0.5 (5)
C10—N2—C6—C5	179.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O2Wⁱ	0.90 (1)	2.22 (1)	3.105 (5)	171 (3)
N4—H4C···N4ⁱⁱ	0.90 (3)	2.58 (3)	3.198 (3)	126 (3)
N3—H3B···O1Wⁱⁱⁱ	0.91 (1)	2.17 (2)	3.048 (6)	165 (4)
N3—H3C···N3ⁱⁱ	0.90 (1)	2.33 (2)	3.122 (4)	147 (3)
O4W—H4WA···O4W^iv	0.86 (2)	2.02 (2)	2.871 (3)	176 (4)
O4W—H4WB···N2	0.87 (2)	1.92 (2)	2.787 (3)	173 (4)
O3W—H3WB···N1	0.87 (2)	1.96 (3)	2.801 (3)	161 (6)
O2W—H2WA···O4W^v	0.84 (2)	2.01 (2)	2.843 (4)	178 (5)
O1W—H1WA···O1W^vi	0.84 (6)	2.15 (6)	2.860 (7)	142 (6)
O2W—H2WB···O2W^vii	0.87 (4)	1.97 (4)	2.812 (5)	161 (3)
O1W—H1WB···O3W	0.85 (3)	2.09 (3)	2.882 (6)	155 (5)

Symmetry codes: (i) x, y, z−1; (ii) −x+1/2, y, z−1/2; (iii) −x+1, −y+1, z−1/2; (iv) −x+1, −y, z−1/2; (v) −x+1, −y, z+1/2; (vi) −x+3/2, y, z+1/2; (vii) −x+1/2, y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₄·4H₂O
M_r	282.30
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	16.7593 (18), 18.1200 (19), 4.7834 (5)
V (Å³)	1452.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.37 × 0.32 × 0.23

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.965, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	7735, 1608, 1432
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.140, 1.14
No. of reflections	1608
No. of parameters	225
No. of restraints	17
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.12

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
N4—H4B···O2Wⁱ	0.895 (10)	2.218 (12)	3.105 (5)	171 (3)
N4—H4C···N4ⁱⁱ	0.90 (3)	2.58 (3)	3.198 (3)	126 (3)
N3—H3B···O1Wⁱⁱⁱ	0.906 (10)	2.165 (16)	3.048 (6)	165 (4)
N3—H3C···N3ⁱⁱ	0.895 (11)	2.33 (2)	3.122 (4)	147 (3)
O4W—H4WA···O4W^iv	0.855 (19)	2.017 (19)	2.871 (3)	176 (4)
O4W—H4WB···N2	0.867 (17)	1.924 (19)	2.787 (3)	173 (4)
O3W—H3WB···N1	0.872 (19)	1.96 (3)	2.801 (3)	161 (6)
O2W—H2WA···O4W^v	0.84 (2)	2.01 (2)	2.843 (4)	178 (5)
O1W—H1WA···O1W^vi	0.84 (6)	2.15 (6)	2.860 (7)	142 (6)
O2W—H2WB···O2W^vii	0.87 (4)	1.97 (4)	2.812 (5)	161 (3)
O1W—H1WB···O3W	0.85 (3)	2.09 (3)	2.882 (6)	155 (5)

Symmetry codes: (i) x, y, z−1; (ii) −x+1/2, y, z−1/2; (iii) −x+1, −y+1, z−1/2; (iv) −x+1, −y, z−1/2; (v) −x+1, −y, z+1/2; (vi) −x+3/2, y, z+1/2; (vii) −x+1/2, y, z+1/2.

Acknowledgements

The authors thank the Program for Liaoning Excellent Talents in Universities for supporting this work (RC-05-11).

References

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