1,5:1′,5′-Bis[1,1′-(ferrocene-1,1′-diyl)diethylidyne]dicarbonohydrazide dihydrate

Zhou, J.; Zhou, H.; Chen, C.-L.; Li, M.-X.

doi:10.1107/S1600536807055407

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1,5:1′,5′-Bis[1,1′-(ferrocene-1,1′-diyl)diethylidyne]dicarbonohydrazide dihydrate

J. Zhou, H. Zhou, C.-L. Chen and M.-X. Li

In the title complex, [Fe₂(C₁₅H₁₆N₄O)₂]·2H₂O, two ferrocene units are bridged by two Schiff base linkers. This molecule lies on an inversion centre, and the asymmetric unit also contains a solvent water molecule. In the crystal structure, complexes and water molecules are connected through weak N—H

O, O—H

N and N—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055407/bh2142sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055407/bh2142Isup2.hkl Contains datablock I

CCDC reference: 672625

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.041
wR factor = 0.076
Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C13     ..       5.63 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Fe1         (3)       3.93

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Much attention has been paid to the chemistry of ferrocene complexes because of their potential applications in material sciences, such as molecular sensors (Beer, 1992; Beer & Smith, 1997), molecular magnetic devices (Miller & Epstein, 1994) and nonlinear optical materials (Nguyen et al., 1999; Long, 1995). In continuation of our research work in the assembly and properties of ferrocene-containing Schiff base compounds (Li et al., 2006), we report here the crystal structure analysis of a bis-ferrocene Schiff base compound, (I).

The compound is a cyclic bis-ferrocene complex lying on an inversion centre. The asymmetric unit is completed with a lattice water molecule. The Fe—C_ring bond lengths range from 2.024 (3) to 2.043 (3) Å (average: 2.034 Å) and are within the expected range (Seiler & Dunitz, 1979; Mammano et al., 1977). The average intra C≐C bond length and C≐ C≐C angle in cyclopentadienyl groups are 1.411 Å and 108°, which are similar to dimensions reported in the literature (Abuhijleh & Woods, 1992; Takusagawa & Koetzle, 1979). The cyclopentadienyl rings in each ferrocenyl fragment are planar and nearly parallel, with a dihedral angle of 3.7 ° at Fe1. The bond lengths N1—C11 and N4—C14 are within the normal range for C═N double bonds, while the N2—C13 and N3—C13 bond lengths suggest that they are single N—C bonds. In addition, the bond length C13═O1 is 1.216 (3) Å, consistent with a carbonyl functionality. Moreover, N1—N2 and N3—N4 bond distances are within the normal range for N—N single bonds. The two side chains are parallel by symmetry, with a torsion angle C11—C10···C4—C14ⁱ of about -61.6 ° [symmetry code: (i) -x, -y, -z].

In the crystal structure, molecules are connected by four different kinds of intra- and intermolecular hydrogen bonds. Besides the intramolecular N2—H2N···N4 and the intermolecular N3—H3N···O1ⁱⁱ interaction present in the ligand [symmetry code: (ii) -x, y, -z - 1/2], there are two hydrogen bonds involving the water molecule.

Related literature top

For related literature, see: Abuhijleh & Woods (1992); Beer (1992); Beer & Smith (1997); Li et al. (2006); Long (1995); Mammano et al. (1977); Miller & Epstein (1994); Nguyen et al. (1999); Seiler & Dunitz (1979); Takusagawa & Koetzle (1979).

Experimental top

All reagents were commercially available and of analytical grade. Diacetylferrocene (0.54 g, 2 mmol) and carbohydrazide (0.18 g, 2 mmol) were mixed in ethanol (15 ml). Five drops of acetic acid were added and the solution was refluxed for 4 h. Then, the solution was cooled to room temperature. Subsequently the dark-red solid formed was filtered off, washed with ethanol and dried in vacuo (yield: 96%). Analysis calculated for C₃₀H₃₆Fe₂N₈O₄: C 52.60, H 5.26, N 16.36%; found: C 52.44, H 5.24, N 16.26%.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. The molecular structure of (I), with atom displacement ellipsoids drawn at the 50% probability level.

Bis(ferrocene-1,1'-diacetyl-carbohydrazide) dihydrate top

Crystal data top

[Fe₂(C₁₅H₁₆N₄O)₂]·2H₂O	F(000) = 1424
M_r = 684.37	D_x = 1.523 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 398 reflections
a = 28.708 (4) Å	θ = 1.7–28.1°
b = 7.9756 (11) Å	µ = 1.02 mm⁻¹
c = 15.305 (2) Å	T = 293 K
β = 121.576 (2)°	Irregular, red
V = 2985.5 (7) Å³	0.20 × 0.18 × 0.16 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2636 independent reflections
Radiation source: fine-focus sealed tube	1718 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
0.3° wide ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −22→34
T_min = 0.822, T_max = 0.853	k = −9→9
7443 measured reflections	l = −18→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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	w = 1/[σ²(F_o²) + (0.0303P)²] where P = (F_o² + 2F_c²)/3
2636 reflections	(Δ/σ)_max < 0.001
213 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Fe₂(C₁₅H₁₆N₄O)₂]·2H₂O	V = 2985.5 (7) Å³
M_r = 684.37	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 28.708 (4) Å	µ = 1.02 mm⁻¹
b = 7.9756 (11) Å	T = 293 K
c = 15.305 (2) Å	0.20 × 0.18 × 0.16 mm
β = 121.576 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2636 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1718 reflections with I > 2σ(I)
T_min = 0.822, T_max = 0.853	R_int = 0.070
7443 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	Δρ_max = 0.38 e Å⁻³
2636 reflections	Δρ_min = −0.25 e Å⁻³
213 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Fe1	0.177935 (16)	0.15125 (6)	0.29805 (3)	0.03626 (15)
N1	0.05413 (9)	0.3357 (3)	0.05970 (17)	0.0385 (6)
O1	0.03726 (8)	0.4466 (3)	−0.12140 (14)	0.0466 (6)
C1	0.21068 (14)	0.0616 (5)	0.2179 (3)	0.0588 (10)
H1A	0.2170	0.1263	0.1706	0.071*
N2	0.00660 (10)	0.3018 (3)	−0.03320 (19)	0.0403 (7)
H2N	−0.0201 (12)	0.258 (4)	−0.033 (2)	0.048*
C2	0.24803 (13)	0.0413 (5)	0.3234 (3)	0.0577 (10)
H2A	0.2848	0.0901	0.3624	0.069*
N3	−0.04608 (10)	0.3296 (3)	−0.20789 (18)	0.0414 (7)
H3N	−0.0501 (12)	0.371 (4)	−0.264 (2)	0.050*
C3	0.22351 (12)	−0.0580 (4)	0.3637 (3)	0.0498 (9)
H3A	0.2402	−0.0909	0.4357	0.060*
N4	−0.08668 (10)	0.2442 (3)	−0.20452 (18)	0.0384 (6)
C4	0.16983 (12)	−0.1025 (4)	0.2821 (2)	0.0400 (8)
C5	0.16302 (13)	−0.0266 (4)	0.1917 (2)	0.0477 (9)
H5A	0.1302	−0.0338	0.1229	0.057*
C6	0.12439 (12)	0.2452 (4)	0.3353 (2)	0.0392 (8)
H6A	0.1012	0.1788	0.3515	0.047*
C7	0.17748 (13)	0.3007 (4)	0.4061 (2)	0.0453 (9)
H7A	0.1977	0.2797	0.4801	0.054*
C8	0.19695 (13)	0.3893 (4)	0.3529 (2)	0.0473 (9)
H8A	0.2330	0.4420	0.3833	0.057*
C9	0.15578 (12)	0.3895 (4)	0.2476 (2)	0.0443 (9)
H9A	0.1582	0.4430	0.1925	0.053*
C10	0.11016 (12)	0.2996 (4)	0.2359 (2)	0.0365 (8)
C11	0.05932 (12)	0.2640 (4)	0.1388 (2)	0.0356 (7)
C12	0.01811 (12)	0.1501 (4)	0.1399 (2)	0.0523 (9)
H12A	0.0057	0.0696	0.0855	0.079*
H12B	−0.0124	0.2151	0.1303	0.079*
H12C	0.0346	0.0928	0.2045	0.079*
C13	0.00185 (13)	0.3665 (4)	−0.1192 (2)	0.0388 (8)
C14	−0.12873 (13)	0.1977 (4)	−0.2894 (2)	0.0400 (8)
C15	−0.13729 (14)	0.2308 (4)	−0.3935 (2)	0.0597 (10)
H15A	−0.1691	0.1713	−0.4445	0.090*
H15B	−0.1059	0.1935	−0.3948	0.090*
H15C	−0.1424	0.3489	−0.4077	0.090*
O1W	0.11076 (12)	0.6713 (4)	0.03268 (19)	0.0670 (8)
H1WB	0.1098 (17)	0.667 (6)	0.082 (3)	0.100*
H1WA	0.0909 (16)	0.601 (5)	−0.007 (3)	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0310 (3)	0.0420 (3)	0.0316 (3)	−0.0025 (2)	0.0135 (2)	−0.0047 (2)
N1	0.0337 (15)	0.0457 (16)	0.0271 (14)	−0.0024 (12)	0.0098 (12)	−0.0014 (13)
O1	0.0437 (14)	0.0591 (15)	0.0347 (13)	−0.0169 (12)	0.0190 (11)	−0.0079 (11)
C1	0.058 (2)	0.071 (3)	0.065 (3)	−0.013 (2)	0.044 (2)	−0.023 (2)
N2	0.0344 (17)	0.0492 (19)	0.0279 (14)	−0.0059 (12)	0.0099 (13)	0.0005 (13)
C2	0.030 (2)	0.066 (3)	0.075 (3)	−0.0046 (18)	0.027 (2)	−0.025 (2)
N3	0.0398 (16)	0.0489 (18)	0.0268 (15)	−0.0068 (14)	0.0115 (14)	0.0002 (13)
C3	0.0325 (19)	0.050 (2)	0.048 (2)	0.0086 (16)	0.0080 (17)	−0.0084 (18)
N4	0.0344 (16)	0.0410 (16)	0.0315 (15)	−0.0029 (12)	0.0115 (13)	−0.0023 (12)
C4	0.038 (2)	0.036 (2)	0.036 (2)	0.0024 (14)	0.0127 (17)	−0.0087 (14)
C5	0.046 (2)	0.056 (2)	0.040 (2)	−0.0061 (17)	0.0216 (17)	−0.0167 (17)
C6	0.040 (2)	0.047 (2)	0.0307 (18)	0.0049 (15)	0.0182 (16)	−0.0014 (15)
C7	0.049 (2)	0.047 (2)	0.0292 (18)	0.0089 (16)	0.0132 (17)	−0.0038 (15)
C8	0.041 (2)	0.044 (2)	0.041 (2)	−0.0066 (15)	0.0112 (17)	−0.0093 (16)
C9	0.042 (2)	0.044 (2)	0.0358 (19)	−0.0049 (15)	0.0128 (16)	0.0078 (15)
C10	0.038 (2)	0.041 (2)	0.0254 (17)	0.0064 (14)	0.0130 (15)	0.0015 (14)
C11	0.0341 (19)	0.0357 (18)	0.0328 (18)	0.0046 (14)	0.0146 (15)	−0.0004 (15)
C12	0.043 (2)	0.061 (2)	0.045 (2)	−0.0050 (18)	0.0174 (17)	0.0080 (18)
C13	0.043 (2)	0.037 (2)	0.0298 (18)	0.0005 (16)	0.0144 (16)	−0.0053 (15)
C14	0.039 (2)	0.0340 (19)	0.0343 (19)	0.0040 (14)	0.0104 (16)	−0.0012 (14)
C15	0.059 (2)	0.063 (3)	0.038 (2)	−0.0139 (19)	0.0119 (18)	−0.0026 (18)
O1W	0.0757 (19)	0.076 (2)	0.0496 (18)	−0.0255 (14)	0.0330 (16)	−0.0168 (15)

Geometric parameters (Å, º) top

Fe1—C9	2.024 (3)	N4—C14	1.280 (3)
Fe1—C1	2.026 (3)	C4—C5	1.426 (4)
Fe1—C5	2.028 (3)	C4—C14ⁱ	1.456 (4)
Fe1—C8	2.032 (3)	C5—H5A	0.9800
Fe1—C3	2.032 (3)	C6—C7	1.401 (4)
Fe1—C4	2.037 (3)	C6—C10	1.421 (4)
Fe1—C2	2.037 (3)	C6—H6A	0.9800
Fe1—C10	2.038 (3)	C7—C8	1.396 (4)
Fe1—C6	2.042 (3)	C7—H7A	0.9800
Fe1—C7	2.043 (3)	C8—C9	1.414 (4)
N1—C11	1.275 (3)	C8—H8A	0.9800
N1—N2	1.387 (3)	C9—C10	1.419 (4)
O1—C13	1.216 (3)	C9—H9A	0.9800
C1—C5	1.397 (4)	C10—C11	1.465 (4)
C1—C2	1.403 (4)	C11—C12	1.498 (4)
C1—H1A	0.9800	C12—H12A	0.9600
N2—C13	1.352 (4)	C12—H12B	0.9600
N2—H2N	0.84 (3)	C12—H12C	0.9600
C2—C3	1.399 (5)	C14—C4ⁱ	1.456 (4)
C2—H2A	0.9800	C14—C15	1.503 (4)
N3—C13	1.366 (4)	C15—H15A	0.9600
N3—N4	1.374 (3)	C15—H15B	0.9600
N3—H3N	0.87 (3)	C15—H15C	0.9600
C3—C4	1.430 (4)	O1W—H1WB	0.78 (4)
C3—H3A	0.9800	O1W—H1WA	0.80 (4)

C9—Fe1—C1	104.65 (14)	C4—C3—H3A	125.8
C9—Fe1—C5	117.27 (13)	Fe1—C3—H3A	125.8
C1—Fe1—C5	40.32 (12)	C14—N4—N3	118.2 (3)
C9—Fe1—C8	40.82 (11)	C5—C4—C3	106.2 (3)
C1—Fe1—C8	118.07 (14)	C5—C4—C14ⁱ	126.2 (3)
C5—Fe1—C8	152.04 (14)	C3—C4—C14ⁱ	127.5 (3)
C9—Fe1—C3	162.16 (13)	C5—C4—Fe1	69.12 (18)
C1—Fe1—C3	68.09 (15)	C3—C4—Fe1	69.24 (17)
C5—Fe1—C3	68.48 (13)	C14ⁱ—C4—Fe1	123.7 (2)
C8—Fe1—C3	126.80 (13)	C1—C5—C4	108.6 (3)
C9—Fe1—C4	153.31 (12)	C1—C5—Fe1	69.78 (18)
C1—Fe1—C4	68.71 (14)	C4—C5—Fe1	69.81 (17)
C5—Fe1—C4	41.07 (12)	C1—C5—H5A	125.7
C8—Fe1—C4	165.25 (12)	C4—C5—H5A	125.7
C3—Fe1—C4	41.15 (11)	Fe1—C5—H5A	125.7
C9—Fe1—C2	123.95 (15)	C7—C6—C10	108.5 (3)
C1—Fe1—C2	40.40 (13)	C7—C6—Fe1	70.02 (18)
C5—Fe1—C2	67.93 (13)	C10—C6—Fe1	69.47 (17)
C8—Fe1—C2	107.38 (14)	C7—C6—H6A	125.7
C3—Fe1—C2	40.22 (13)	C10—C6—H6A	125.7
C4—Fe1—C2	68.56 (13)	Fe1—C6—H6A	125.7
C9—Fe1—C10	40.91 (12)	C8—C7—C6	108.3 (3)
C1—Fe1—C10	123.67 (14)	C8—C7—Fe1	69.50 (18)
C5—Fe1—C10	106.42 (12)	C6—C7—Fe1	69.87 (17)
C8—Fe1—C10	68.56 (12)	C8—C7—H7A	125.8
C3—Fe1—C10	156.62 (13)	C6—C7—H7A	125.8
C4—Fe1—C10	119.98 (12)	Fe1—C7—H7A	125.8
C2—Fe1—C10	160.94 (14)	C7—C8—C9	108.3 (3)
C9—Fe1—C6	68.27 (13)	C7—C8—Fe1	70.42 (18)
C1—Fe1—C6	162.62 (13)	C9—C8—Fe1	69.30 (17)
C5—Fe1—C6	127.40 (13)	C7—C8—H8A	125.8
C8—Fe1—C6	67.67 (13)	C9—C8—H8A	125.8
C3—Fe1—C6	123.19 (14)	Fe1—C8—H8A	125.8
C4—Fe1—C6	110.05 (13)	C8—C9—C10	108.0 (3)
C2—Fe1—C6	156.61 (13)	C8—C9—Fe1	69.88 (17)
C10—Fe1—C6	40.78 (11)	C10—C9—Fe1	70.08 (17)
C9—Fe1—C7	68.12 (13)	C8—C9—H9A	126.0
C1—Fe1—C7	153.75 (14)	C10—C9—H9A	126.0
C5—Fe1—C7	165.66 (14)	Fe1—C9—H9A	126.0
C8—Fe1—C7	40.08 (12)	C9—C10—C6	106.9 (3)
C3—Fe1—C7	110.74 (13)	C9—C10—C11	126.1 (3)
C4—Fe1—C7	128.88 (13)	C6—C10—C11	127.0 (3)
C2—Fe1—C7	121.40 (13)	C9—C10—Fe1	69.02 (17)
C10—Fe1—C7	68.29 (12)	C6—C10—Fe1	69.75 (16)
C6—Fe1—C7	40.11 (11)	C11—C10—Fe1	124.1 (2)
C11—N1—N2	116.7 (3)	N1—C11—C10	115.8 (3)
C5—C1—C2	108.4 (3)	N1—C11—C12	125.6 (3)
C5—C1—Fe1	69.90 (18)	C10—C11—C12	118.7 (3)
C2—C1—Fe1	70.23 (19)	C11—C12—H12A	109.5
C5—C1—H1A	125.8	C11—C12—H12B	109.5
C2—C1—H1A	125.8	H12A—C12—H12B	109.5
Fe1—C1—H1A	125.8	C11—C12—H12C	109.5
C13—N2—N1	117.8 (3)	H12A—C12—H12C	109.5
C13—N2—H2N	122 (2)	H12B—C12—H12C	109.5
N1—N2—H2N	119 (2)	O1—C13—N2	124.6 (3)
C3—C2—C1	108.4 (3)	O1—C13—N3	120.5 (3)
C3—C2—Fe1	69.70 (18)	N2—C13—N3	114.9 (3)
C1—C2—Fe1	69.38 (19)	N4—C14—C4ⁱ	116.4 (3)
C3—C2—H2A	125.8	N4—C14—C15	124.6 (3)
C1—C2—H2A	125.8	C4ⁱ—C14—C15	118.9 (3)
Fe1—C2—H2A	125.8	C14—C15—H15A	109.5
C13—N3—N4	120.1 (3)	C14—C15—H15B	109.5
C13—N3—H3N	116 (2)	H15A—C15—H15B	109.5
N4—N3—H3N	123 (2)	C14—C15—H15C	109.5
C2—C3—C4	108.4 (3)	H15A—C15—H15C	109.5
C2—C3—Fe1	70.1 (2)	H15B—C15—H15C	109.5
C4—C3—Fe1	69.61 (17)	H1WB—O1W—H1WA	109 (4)
C2—C3—H3A	125.8

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N4	0.84 (3)	2.30 (3)	2.628 (3)	104 (2)
N3—H3N···O1ⁱⁱ	0.87 (3)	2.06 (3)	2.908 (3)	164 (3)
O1W—H1WA···O1	0.80 (4)	2.04 (4)	2.831 (3)	172 (4)
O1W—H1WB···N4ⁱⁱⁱ	0.78 (4)	2.39 (4)	3.123 (4)	156 (4)

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

Experimental details

Crystal data
Chemical formula	[Fe₂(C₁₅H₁₆N₄O)₂]·2H₂O
M_r	684.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	28.708 (4), 7.9756 (11), 15.305 (2)
β (°)	121.576 (2)
V (Å³)	2985.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.02
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.822, 0.853
No. of measured, independent and observed [I > 2σ(I)] reflections	7443, 2636, 1718
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.076, 0.81
No. of reflections	2636
No. of parameters	213
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.25

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N4	0.84 (3)	2.30 (3)	2.628 (3)	104 (2)
N3—H3N···O1ⁱ	0.87 (3)	2.06 (3)	2.908 (3)	164 (3)
O1W—H1WA···O1	0.80 (4)	2.04 (4)	2.831 (3)	172 (4)
O1W—H1WB···N4ⁱⁱ	0.78 (4)	2.39 (4)	3.123 (4)	156 (4)

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

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