Diamminebis[5-(pyrimidin-2-yl-κN¹)tetra­zolato-κN¹]copper(II) dihydrate

The title compound, [Cu(C₅H₃N₆)₂(NH₃)₂]·2H₂O, consists of a mononuclear copper complex and two solvent water mol­ecules. The center Cu^II ion is coordinated by two NH₃ and two 5-(pyrimidin-2-yl)tetra­zolato ligands through the tetra­zole N atoms in the 1 positions to form a square geometry. The two axial positions are occupied by weakly coordinated pyrimidinyl N atoms, thus giving rise to a highly distorted octa­hedral geometry. Furthermore, extensive inter­molecular hydrogen-bond inter­actions lead to the formation of a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.097
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.77
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.64 Ratio
PLAT420_ALERT_2_C D-H Without Acceptor       N13    -   H13C   ...          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.849(10) ......       4.00 su-Ra
              O2W  -H2WA    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.848(10) ......       4.00 su-Ra
              O2W  -H2WB    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Ra
              O2W  -H1#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Ra
              O2W  -H3#     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.20(4), Rep   2.199(12) ......       3.33 su-Ra
              H3#  -N8      1.555   1.655

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.775
            Tmax scaled      0.775 Tmin scaled      0.756
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.14
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

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

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

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S1. Comment

The crystal structures of Fe(II) and Co(II) complexes with 5-(pyrimidin-2-yl)tetrazolate ligand have been reported recently (Rodríguez et al., 2005), which feature a two-dimensional square-grid-like network. And, the ligands coordinate to metal atoms through one of the pyrimidinyl nitrogen atoms and the 1- and 3-positon tetrazole nitrogen atoms. The title complex, diamminobis[5-(pyrimidin-2-yl-κN¹)tetrazolato-κN¹]copper(II) dehydrate (I) performs a mono-nuclear structure (Fig. 1), in which the center Cu^II atom, located on a normal position, is normally coordinated by two NH₃ and two ligand molecules using tetrazole N atoms in 1-position to form a square geometry. Simultaneously, two apical positions in Cu^II atom form weak coordination (Cu1-N11 = 2.429 (2) and Cu1-N5 = 2.728 (2) Å) with two pyrimidinyl N atoms of two ligands, thus giving a highly distorted octahedral geometry (see Table 1). In addition, a three-dimensional supramolecular framework (Fig. 2) is formed by the intermolecular extensive N-H···O, N-H···N, O-H···N and O-H···O hydrogen-bond interactions between parking water molecules and complex molecules. The hydrogen bond parameters are listed in Table 2.

Related literature

For related literature, see: Demko & Sharpless (2001); Rodríguez et al. (2005).

S2. Experimental

TThe ligand, 2-(1H-tetrazol-5-yl)pyrimidine (L) was synthesized according to the literature method (Demko & Sharpless, 2001). CuCl₂.2H₂O (34 mg, 0.2 mmol) and L (60 mg, 0.4 mmol) were dissolved in ammonium hydroxide (20%, 10 ml). The solution was filtered, and then filtrate was allowed to stand for about 10 days. Blue crystals of (I) were isolated in about 30% yield.

S3. Refinement

H atoms bound to carbon and amine were included in calculated positions and treated in the subsequent refinement as riding atoms, with C—H = 0.93 and N—H = 0.89 Å and U_iso(H) = 1.2 and 1.5 U_eq(C and N), respectively. The H atoms of the water molecules were located in Fourier difference maps and refined with isotropic displacement parameters set at 1.5 times those of the parent O atoms.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Three-dimensional hydrogen-bonded network.

Diamminebis[5-(pyrimidin-2-yl-κN¹)tetrazolato-κN¹]copper(II) dihydrate

Crystal data

[Cu(C5H3N6)2(NH3)2]·2H2O	Z = 2
Mr = 427.91	F(000) = 438
Triclinic, P1	Dx = 1.605 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1533 (12) Å	Cell parameters from 3035 reflections
b = 9.5708 (16) Å	θ = 2.5–26.4°
c = 13.155 (2) Å	µ = 1.28 mm^−1
α = 97.048 (3)°	T = 294 K
β = 90.214 (2)°	Block, blue
γ = 97.777 (3)°	0.22 × 0.22 × 0.20 mm
V = 885.4 (2) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3549 independent reflections
Radiation source: fine-focus sealed tube	3104 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 26.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −6→8
Tmin = 0.975, Tmax = 1.000	k = −11→10
5086 measured reflections	l = −16→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0583P)^2 + 0.2049P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3549 reflections	Δρmax = 0.56 e Å^−3
257 parameters	Δρmin = −0.63 e Å^−3
4 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.096 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.23179 (3)	0.95624 (3)	0.245828 (19)	0.02515 (13)
N1	0.2492 (3)	1.0675 (2)	0.38683 (14)	0.0257 (4)
N2	0.2601 (3)	1.2084 (2)	0.41174 (16)	0.0352 (5)
N3	0.2667 (3)	1.2353 (2)	0.51209 (17)	0.0402 (5)
N4	0.2606 (3)	1.1139 (2)	0.55440 (15)	0.0333 (5)
N5	0.2149 (3)	0.7757 (2)	0.39173 (18)	0.0384 (5)
N6	0.2597 (4)	0.8204 (2)	0.57417 (18)	0.0448 (6)
N7	0.2131 (3)	0.8657 (2)	0.09642 (15)	0.0285 (4)
N8	0.1767 (3)	0.7331 (2)	0.04961 (17)	0.0389 (5)
N9	0.1783 (4)	0.7390 (3)	−0.05057 (18)	0.0469 (6)
N10	0.2150 (3)	0.8732 (3)	−0.07049 (16)	0.0410 (5)
N11	0.2867 (3)	1.1532 (2)	0.14470 (15)	0.0314 (4)
N12	0.2938 (3)	1.1822 (3)	−0.03200 (16)	0.0418 (5)
C1	0.2495 (3)	1.0122 (2)	0.47534 (17)	0.0246 (5)
C2	0.2402 (3)	0.8601 (2)	0.48099 (18)	0.0282 (5)
C3	0.2101 (5)	0.6381 (3)	0.3973 (3)	0.0554 (8)
H3A	0.1921	0.5751	0.3373	0.067*
C4	0.2309 (5)	0.5847 (3)	0.4888 (3)	0.0641 (10)
H4A	0.2287	0.4879	0.4916	0.077*
C5	0.2547 (5)	0.6800 (3)	0.5747 (3)	0.0642 (10)
H5A	0.2683	0.6461	0.6373	0.077*
C6	0.2364 (3)	0.9490 (3)	0.02177 (17)	0.0284 (5)
C7	0.2752 (3)	1.1045 (3)	0.04536 (18)	0.0291 (5)
C8	0.3217 (4)	1.2939 (3)	0.1692 (2)	0.0407 (6)
H8A	0.3323	1.3316	0.2379	0.049*
C9	0.3426 (4)	1.3842 (3)	0.0953 (2)	0.0478 (7)
H9A	0.3662	1.4822	0.1124	0.057*
C10	0.3270 (4)	1.3236 (3)	−0.0047 (2)	0.0502 (7)
H10A	0.3399	1.3827	−0.0560	0.060*
N14	0.5061 (3)	0.9386 (3)	0.24816 (16)	0.0369 (5)
H14A	0.5254	0.8682	0.2835	0.055*
H14B	0.5704	1.0196	0.2777	0.055*
H14C	0.5449	0.9203	0.1843	0.055*
N13	−0.0473 (3)	0.9502 (3)	0.24504 (15)	0.0383 (5)
H13A	−0.0986	0.8813	0.2801	0.057*
H13B	−0.0915	0.9334	0.1807	0.057*
H13C	−0.0768	1.0332	0.2739	0.057*
O1W	0.6222 (4)	0.6186 (4)	0.2726 (2)	0.0799 (8)
H2WA	0.895 (7)	0.449 (3)	0.145 (4)	0.120*
H1WA	0.655 (7)	0.643 (6)	0.3348 (14)	0.120*
O2W	0.9450 (4)	0.5292 (3)	0.17569 (19)	0.0651 (6)
H2WB	1.008 (6)	0.579 (4)	0.135 (3)	0.098*
H1WB	0.731 (3)	0.610 (6)	0.251 (3)	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01906 (17)	0.0352 (2)	0.02059 (18)	0.00532 (11)	−0.00056 (10)	−0.00088 (11)
N1	0.0269 (10)	0.0287 (10)	0.0217 (9)	0.0063 (8)	0.0015 (7)	0.0010 (8)
N2	0.0455 (13)	0.0277 (10)	0.0331 (11)	0.0075 (9)	0.0035 (9)	0.0042 (9)
N3	0.0575 (15)	0.0301 (11)	0.0322 (12)	0.0083 (10)	0.0039 (10)	−0.0019 (9)
N4	0.0457 (12)	0.0274 (10)	0.0259 (10)	0.0048 (9)	0.0015 (9)	0.0000 (8)
N5	0.0390 (12)	0.0318 (11)	0.0415 (13)	0.0038 (9)	0.0001 (10)	−0.0051 (9)
N6	0.0580 (15)	0.0366 (12)	0.0408 (13)	0.0028 (11)	−0.0064 (11)	0.0130 (10)
N7	0.0244 (10)	0.0329 (10)	0.0269 (10)	0.0040 (8)	−0.0010 (8)	−0.0012 (8)
N8	0.0427 (13)	0.0353 (12)	0.0363 (12)	0.0059 (10)	−0.0024 (9)	−0.0054 (9)
N9	0.0540 (15)	0.0445 (14)	0.0380 (13)	0.0049 (11)	−0.0038 (11)	−0.0101 (10)
N10	0.0474 (13)	0.0467 (14)	0.0263 (11)	0.0057 (11)	−0.0018 (9)	−0.0056 (10)
N11	0.0341 (11)	0.0340 (11)	0.0259 (10)	0.0057 (9)	0.0019 (8)	0.0016 (8)
N12	0.0441 (13)	0.0507 (14)	0.0296 (11)	−0.0030 (11)	−0.0026 (9)	0.0113 (10)
C1	0.0214 (10)	0.0305 (12)	0.0211 (11)	0.0040 (9)	0.0002 (8)	0.0004 (9)
C2	0.0238 (11)	0.0277 (12)	0.0327 (12)	0.0026 (9)	0.0006 (9)	0.0039 (10)
C3	0.0542 (19)	0.0307 (15)	0.076 (2)	0.0039 (13)	−0.0033 (16)	−0.0113 (14)
C4	0.067 (2)	0.0276 (15)	0.099 (3)	0.0053 (14)	−0.006 (2)	0.0125 (17)
C5	0.081 (2)	0.0436 (18)	0.074 (2)	0.0062 (17)	−0.0107 (19)	0.0299 (17)
C6	0.0199 (10)	0.0409 (13)	0.0234 (11)	0.0045 (9)	−0.0001 (8)	−0.0007 (9)
C7	0.0202 (11)	0.0407 (13)	0.0258 (12)	0.0033 (9)	0.0002 (9)	0.0033 (10)
C8	0.0456 (15)	0.0358 (14)	0.0389 (14)	0.0051 (11)	0.0020 (12)	−0.0015 (11)
C9	0.0487 (17)	0.0344 (14)	0.0589 (19)	−0.0019 (12)	0.0016 (14)	0.0089 (13)
C10	0.0549 (18)	0.0475 (17)	0.0496 (17)	−0.0036 (14)	0.0000 (14)	0.0239 (14)
N14	0.0262 (10)	0.0590 (14)	0.0258 (10)	0.0120 (10)	−0.0029 (8)	0.0000 (9)
N13	0.0230 (10)	0.0663 (15)	0.0250 (10)	0.0072 (10)	−0.0001 (8)	0.0023 (10)
O1W	0.0835 (19)	0.094 (2)	0.0572 (16)	0.0256 (17)	−0.0117 (15)	−0.0251 (15)
O2W	0.0788 (18)	0.0543 (14)	0.0550 (14)	0.0030 (12)	0.0053 (12)	−0.0155 (11)

Geometric parameters (Å, º)

Cu1—N1	2.0170 (18)	N12—C10	1.345 (4)
Cu1—N5	2.728 (2)	C1—C2	1.459 (3)
Cu1—N7	2.0447 (19)	C3—C4	1.379 (5)
Cu1—N11	2.429 (2)	C3—H3A	0.9300
Cu1—N13	1.990 (2)	C4—C5	1.357 (5)
Cu1—N14	1.992 (2)	C4—H4A	0.9300
N1—C1	1.337 (3)	C5—H5A	0.9300
N1—N2	1.339 (3)	C6—C7	1.471 (3)
N2—N3	1.313 (3)	C8—C9	1.374 (4)
N3—N4	1.344 (3)	C8—H8A	0.9300
N4—C1	1.329 (3)	C9—C10	1.369 (4)
N5—C3	1.324 (4)	C9—H9A	0.9300
N5—C2	1.338 (3)	C10—H10A	0.9300
N6—C2	1.339 (3)	N14—H14A	0.8900
N6—C5	1.341 (4)	N14—H14B	0.8900
N7—N8	1.332 (3)	N14—H14C	0.8900
N7—C6	1.336 (3)	N13—H13A	0.8900
N8—N9	1.326 (3)	N13—H13B	0.8900
N9—N10	1.334 (3)	N13—H13C	0.8900
N10—C6	1.332 (3)	O1W—H1WA	0.846 (10)
N11—C7	1.331 (3)	O1W—H1WB	0.843 (10)
N11—C8	1.334 (3)	O2W—H2WA	0.849 (10)
N12—C7	1.329 (3)	O2W—H2WB	0.848 (10)
N13—Cu1—N14	173.45 (9)	C4—C3—H3A	118.8
N13—Cu1—N1	90.18 (8)	C5—C4—C3	117.0 (3)
N14—Cu1—N1	91.95 (8)	C5—C4—H4A	121.5
N13—Cu1—N7	88.98 (8)	C3—C4—H4A	121.5
N14—Cu1—N7	89.61 (8)	N6—C5—C4	123.4 (3)
N1—Cu1—N7	173.28 (7)	N6—C5—H5A	118.3
N13—Cu1—N11	94.55 (8)	C4—C5—H5A	118.3
N14—Cu1—N11	91.24 (8)	N10—C6—N7	111.5 (2)
N1—Cu1—N11	98.88 (7)	N10—C6—C7	127.4 (2)
N7—Cu1—N11	74.54 (7)	N7—C6—C7	121.1 (2)
C1—N1—N2	106.16 (18)	N12—C7—N11	126.4 (2)
C1—N1—Cu1	125.67 (16)	N12—C7—C6	118.5 (2)
N2—N1—Cu1	128.17 (15)	N11—C7—C6	115.1 (2)
N3—N2—N1	107.98 (19)	N11—C8—C9	121.5 (3)
N2—N3—N4	110.3 (2)	N11—C8—H8A	119.2
C1—N4—N3	104.76 (19)	C9—C8—H8A	119.2
C3—N5—C2	115.6 (3)	C10—C9—C8	117.1 (3)
C2—N6—C5	114.4 (3)	C10—C9—H9A	121.5
N8—N7—C6	105.87 (19)	C8—C9—H9A	121.5
N8—N7—Cu1	134.76 (17)	N12—C10—C9	122.9 (3)
C6—N7—Cu1	119.35 (16)	N12—C10—H10A	118.6
N9—N8—N7	107.8 (2)	C9—C10—H10A	118.6
N8—N9—N10	110.8 (2)	Cu1—N14—H14A	109.5
C6—N10—N9	104.1 (2)	Cu1—N14—H14B	109.5
C7—N11—C8	116.9 (2)	H14A—N14—H14B	109.5
C7—N11—Cu1	109.90 (16)	Cu1—N14—H14C	109.5
C8—N11—Cu1	133.21 (17)	H14A—N14—H14C	109.5
C7—N12—C10	115.2 (2)	H14B—N14—H14C	109.5
N4—C1—N1	110.8 (2)	Cu1—N13—H13A	109.5
N4—C1—C2	126.1 (2)	Cu1—N13—H13B	109.5
N1—C1—C2	123.1 (2)	H13A—N13—H13B	109.5
N5—C2—N6	127.2 (2)	Cu1—N13—H13C	109.5
N5—C2—C1	116.0 (2)	H13A—N13—H13C	109.5
N6—C2—C1	116.8 (2)	H13B—N13—H13C	109.5
N5—C3—C4	122.4 (3)	H1WA—O1W—H1WB	96 (5)
N5—C3—H3A	118.8	H2WA—O2W—H2WB	112 (5)
N13—Cu1—N1—C1	92.85 (19)	C3—N5—C2—N6	−0.5 (4)
N14—Cu1—N1—C1	−80.95 (19)	C3—N5—C2—C1	178.8 (2)
N11—Cu1—N1—C1	−172.51 (18)	C5—N6—C2—N5	0.8 (4)
N13—Cu1—N1—N2	−86.2 (2)	C5—N6—C2—C1	−178.4 (3)
N14—Cu1—N1—N2	100.0 (2)	N4—C1—C2—N5	175.0 (2)
N11—Cu1—N1—N2	8.5 (2)	N1—C1—C2—N5	−5.5 (3)
C1—N1—N2—N3	0.0 (3)	N4—C1—C2—N6	−5.7 (4)
Cu1—N1—N2—N3	179.19 (16)	N1—C1—C2—N6	173.8 (2)
N1—N2—N3—N4	0.1 (3)	C2—N5—C3—C4	−0.4 (5)
N2—N3—N4—C1	−0.2 (3)	N5—C3—C4—C5	0.7 (5)
N13—Cu1—N7—N8	−83.5 (2)	C2—N6—C5—C4	−0.4 (5)
N14—Cu1—N7—N8	90.1 (2)	C3—C4—C5—N6	−0.3 (6)
N11—Cu1—N7—N8	−178.6 (2)	N9—N10—C6—N7	−0.3 (3)
N14—Cu1—N7—C6	−91.74 (18)	N9—N10—C6—C7	−178.6 (2)
N11—Cu1—N7—C6	−0.35 (16)	N8—N7—C6—N10	0.3 (3)
C6—N7—N8—N9	−0.1 (3)	Cu1—N7—C6—N10	−178.39 (16)
Cu1—N7—N8—N9	178.26 (17)	N8—N7—C6—C7	178.7 (2)
N7—N8—N9—N10	−0.1 (3)	Cu1—N7—C6—C7	0.0 (3)
N8—N9—N10—C6	0.3 (3)	C10—N12—C7—N11	−0.2 (4)
N13—Cu1—N11—C7	−86.98 (16)	C10—N12—C7—C6	179.3 (2)
N14—Cu1—N11—C7	89.95 (16)	C8—N11—C7—N12	−0.5 (4)
N1—Cu1—N11—C7	−177.88 (15)	Cu1—N11—C7—N12	178.6 (2)
N7—Cu1—N11—C7	0.69 (15)	C8—N11—C7—C6	180.0 (2)
N13—Cu1—N11—C8	91.9 (2)	Cu1—N11—C7—C6	−0.9 (2)
N14—Cu1—N11—C8	−91.1 (2)	N10—C6—C7—N12	−0.7 (4)
N1—Cu1—N11—C8	1.0 (2)	N7—C6—C7—N12	−178.8 (2)
N7—Cu1—N11—C8	179.6 (3)	N10—C6—C7—N11	178.8 (2)
N3—N4—C1—N1	0.2 (3)	N7—C6—C7—N11	0.7 (3)
N3—N4—C1—C2	179.8 (2)	C7—N11—C8—C9	0.8 (4)
N2—N1—C1—N4	−0.2 (3)	Cu1—N11—C8—C9	−178.1 (2)
Cu1—N1—C1—N4	−179.34 (15)	N11—C8—C9—C10	−0.4 (4)
N2—N1—C1—C2	−179.7 (2)	C7—N12—C10—C9	0.6 (4)
Cu1—N1—C1—C2	1.1 (3)	C8—C9—C10—N12	−0.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14A···O1W	0.89	2.56	3.332 (4)	145
N14—H14A···N4^i	0.89	2.59	3.209 (3)	127
N14—H14B···N6^i	0.89	2.52	3.345 (3)	154
N14—H14C···N12^ii	0.89	2.48	3.339 (3)	162
N13—H13A···N4^iii	0.89	2.47	3.137 (3)	132
N13—H13B···N12^iv	0.89	2.48	3.325 (3)	158
O2W—H2WA···N9^v	0.85 (1)	2.07 (2)	2.901 (3)	168 (5)
O1W—H1WA···N3^i	0.85 (1)	2.23 (2)	3.053 (3)	165 (5)
O1W—H1WA···N4^i	0.85 (1)	2.59 (4)	3.227 (3)	133 (5)
O2W—H2WB···N8^vi	0.85 (1)	2.20 (1)	3.041 (4)	172 (4)
O1W—H1WB···O2W	0.84 (1)	2.01 (2)	2.825 (4)	161 (5)

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