2-Amino­pyridinium trans-diaqua­bis­(oxalato-κ²O,O)chromate(III)

In the title hybrid salt, (C₅H₇N₂)[Cr(H₂O)₂(C₂O₄)₂], the Cr^III ion is coordinated in a slightly distorted octa­hedral environment by four O atoms from two oxalate ligands in the equatorial plane and by two water O atoms in the axial sites. The 2-amino­pyridinium cation is disordered over two sets of sites in a 0.800 (7):0.200 (7) ratio. In the crystal, N—H...O and O—H...O hydrogen bonds connect the components into a three-dimensional network. The crystal studied was an inversion twin with components in a ratio 0.75 (2):0.25 (2).

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.039
• wR factor = 0.088
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT223_ALERT_4_B Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...        4.1 Ratio

Alert level C
SHFSU01_ALERT_2_C  Test not performed. _refine_ls_shift/su_max and
            _refine_ls_shift/esd_max not present.
            Absolute value of the parameter shift to su ratio given   0.001
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT915_ALERT_3_C Low Friedel Pair Coverage ......................         90 Perc.
PLAT922_ALERT_1_C wR2 in the CIF and FCF Differ by ...............     0.0023
PLAT923_ALERT_1_C S    values in the CIF and FCF Differ by .......      0.134
PLAT927_ALERT_1_C Reported and Calculated  wR2 Differ by .........     0.0022
PLAT928_ALERT_1_C Reported and Calculated    S value   Differ by .      0.134

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.66
           From the CIF: _reflns_number_total               3716
           Count of symmetry unique reflns         2009
           Completeness (_total/calc)            184.97%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1707
           Fraction of Friedel pairs measured     0.850
           Are heavy atom types Z>Si present        yes
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         20
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............          6
PLAT033_ALERT_4_G Flack x Parameter Value Deviates from Zero .....      0.250
PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ...................        100 Perc.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          9
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          !
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         21
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         83

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   8 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

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


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Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: Main Autor: Idea and writes the manuscript Synthesis and crystal growth: Sign\'e and Gouet Figures drawing and Discussion: B\'elomb\'e Structure solution and refinement: Fokwa and Mbarki

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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S1. Comment

The coordination chemistry of oxalates (C₂O₄^2-) continues to receive considerable attention, largely due to the ability of this ion to act as a remarkably flexible ligand system in complexations with a wide range of metal ions (Martin et al., 2007). In the course of recent years, a few organic–inorganic hybrid salts of the form A[Cr(H₂O)₂(C₂O₄)₂].xH₂O (A⁺ = aromatic iminium cation, 0 ≤ x ≤ 1) have been reported (Bélombé et al., 2009; Nenwa et al., 2010; Chérif et al., 2011; Chérif, Abdelhak et al., 2012; Chérif, Zid et al., 2012). These salts form crystal structures for which a set of interesting solid state properties, magnetic interactions, optical and/or optoelectronic effects, or combinations thereof may be expected. With the pyridinium core cation for instance, the resulting salts diversely crystallize in non-centrosymmetric space groups Fdd2 and Pna2₁ (Chérif, Abdelhak et al., 2012, 2011), or in the centrosymmetric space groups P2₁/c (Chérif, Zid et al., 2012) and C2/c (Nenwa et al., 2010), depending on the nature of the subtituent and/or the position of substitution. In the present contribution, we report the structure of a homologous salt in the non-centrosymmetric I2/a space group.

The asymmetric unit of the title compound is shown in Fig. 1. The main geometrical features of the [C₅H₇N₂]⁺ cation are in agreement with those found in salts with similar cationic entities (Bélombé et al., 2009; Nenwa et al., 2010; Chérif et al., 2011; Chérif, Abdelhak et al., 2012; Chérif, Zid et al., 2012). The Cr^III ion adopts a slightly distorted octahedral coordination environment involving four oxalate O atoms (O13, O14, O21, O23) in equatorial sites and two water O atoms (OW1, OW2) in axial sites. The equatorial Cr—O distances are shorter than the axial Cr—O distances. The bond distances in the complex anion (Table 1) are comparable with those reported for the 4-dimethylaminopyridinium compound (Nenwa et al., 2010).

In the crystal structure, intermolecular N—H···O (carbonyl) and O—H···O hydrogen bonds (Table 2, Fig. 2) connect the components into a three-dimensional network.

Related literature

For general background to the coordination chemistry of oxalates, see: Martin et al. (2007). For the structural characterization of organic–inorganic salts containing the [Cr(H₂O)₂(C₂O₄)₂]^- anion, see: Bélombé et al. (2009); Nenwa et al. (2010); Chérif et al. (2011); Chérif, Abdelhak et al. (2012); Chérif, Zid et al. (2012).

S2. Experimental

A mixture of 2-aminopyridine (1 mmol, 100 mg) and oxalic acid (2 mmol, 260 mg) was dissolved in 30 ml of ethanol. An aqueous solution (20 ml) of CrCl₃.6H₂O (1 mmol, 266.5 mg) was added in successive small portions and stirred for 4 h continuously. The final blue–violet solution obtained was left at room temperature and crystals suitable for X-ray diffraction were obtained after a few days.

S3. Refinement

The H atoms were positioned geometrically, with C—H, N—H distances of 0.95 and 0.86 Å respectively, and constrained to ride on their parent atoms, with U_iso(H) = 1.2U_eq(C,N). The water H atoms were initially located in a difference Fourier map and refined with distance restraints of d(O—H1) = 0.83 (2) with all U_iso(H) values restained to have the same value.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: WinGX Farrugia (1999).

Figures

	Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn drawn at the 50% probability level. The minor component of disorder in the cation is not shown.
	Fig. 2. Crystal packing of the title compound, showing the components linked via N—H···O and O—H···O hydrogen bonds (dashed lines) forming a three-dimensional network. The disorder is not shown.

2-Aminopyridinium trans-diaquabis(oxalato-κ²O,O)chromate(III)

Crystal data

(C5H7N2)[Cr(H2O)2(C2O4)2]	F(000) = 732
Mr = 359.20	Dx = 1.843 Mg m^−3
Monoclinic, Ia	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I -2ya	Cell parameters from 3716 reflections
a = 6.8627 (14) Å	θ = 2.4–30.7°
b = 19.434 (4) Å	µ = 0.94 mm^−1
c = 9.854 (2) Å	T = 100 K
β = 99.90 (3)°	Prism, blue
V = 1294.7 (5) Å^3	0.23 × 0.15 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer	3716 independent reflections
Radiation source: fine-focus sealed tube	3391 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ϕ and ω scans	θmax = 30.7°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
Tmin = 0.811, Tmax = 0.912	k = −27→26
9645 measured reflections	l = −13→13

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0372P)^2 + 2.2822P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3716 reflections	Δρmax = 0.52 e Å^−3
241 parameters	Δρmin = −0.30 e Å^−3
21 restraints	Absolute structure: Flack (1983), 1793 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.25 (2)

Special details

Experimental. A mixture of 2-aminopyridine (1 mmol, 100 mg) and oxalic acid (2 mmol, 260 mg) was dissolved in 30 ml of ethanol. An aqueous solution (20 ml) of CrCl3.6H2O (1 mmol, 266.5 mg) was added in successive small portions and stirred for 4 h continuously. The final blue-violet solution obtained was left at room temperature and crystals suitable for X-ray diffraction were obtained after a few days.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
Cr1	0.19814 (16)	0.342519 (16)	0.68436 (13)	0.01109 (9)
C11	0.2455 (5)	0.48129 (16)	0.7396 (4)	0.0177 (7)
C12	0.1032 (5)	0.47555 (17)	0.6004 (3)	0.0195 (7)
O11	0.2936 (4)	0.53790 (12)	0.7885 (3)	0.0321 (6)
O12	0.0359 (4)	0.52679 (12)	0.5348 (3)	0.0282 (6)
O14	0.3031 (4)	0.42294 (13)	0.7934 (3)	0.0183 (5)
O13	0.0649 (4)	0.41336 (12)	0.5602 (3)	0.0180 (5)
C21	0.2715 (5)	0.20807 (17)	0.7621 (3)	0.0135 (6)
C22	0.1519 (5)	0.20649 (17)	0.6142 (4)	0.0145 (6)
O22	0.0979 (3)	0.26575 (12)	0.5654 (2)	0.0155 (5)
O21	0.3152 (3)	0.26885 (12)	0.8085 (2)	0.0134 (5)
O24	0.3136 (5)	0.15470 (11)	0.8242 (3)	0.0221 (7)
O23	0.1161 (5)	0.15033 (11)	0.5525 (3)	0.0201 (6)
OW1	−0.0319 (4)	0.33987 (10)	0.7854 (3)	0.0145 (5)
OW2	0.4360 (4)	0.34394 (10)	0.5912 (3)	0.0180 (5)
N1	0.2574 (5)	0.01644 (13)	0.7419 (4)	0.0213 (9)	0.800 (7)
H1A	0.3224	0.0271	0.8241	0.026*	0.800 (7)
H1B	0.2100	0.0492	0.6839	0.026*	0.800 (7)
N2	0.3078 (5)	−0.09776 (18)	0.7994 (3)	0.0141 (8)	0.800 (7)
H2	0.3733	−0.0840	0.8794	0.017*	0.800 (7)
C1	0.2309 (6)	−0.04927 (14)	0.7051 (4)	0.0134 (8)	0.800 (7)
C6	0.1323 (6)	−0.0728 (2)	0.5772 (4)	0.0150 (8)	0.800 (7)
H6	0.0779	−0.0409	0.5080	0.018*	0.800 (7)
C5	0.1146 (6)	−0.1417 (2)	0.5524 (4)	0.0180 (9)	0.800 (7)
H5	0.0494	−0.1574	0.4650	0.022*	0.800 (7)
C4	0.1916 (6)	−0.19022 (15)	0.6546 (4)	0.0161 (9)	0.800 (7)
H4	0.1756	−0.2382	0.6383	0.019*	0.800 (7)
C3	0.2877 (6)	−0.1664 (2)	0.7750 (4)	0.0152 (9)	0.800 (7)
H3	0.3429	−0.1980	0.8447	0.018*	0.800 (7)
N1A	0.161 (2)	0.0179 (4)	0.6157 (15)	0.031 (4)*	0.200 (7)
H1A1	0.2089	0.0479	0.6796	0.037*	0.200 (7)
H1A2	0.0995	0.0323	0.5348	0.037*	0.200 (7)
N2A	0.275 (2)	−0.0690 (6)	0.7682 (10)	0.021 (3)*	0.200 (7)
H2A1	0.3211	−0.0370	0.8285	0.025*	0.200 (7)
C1A	0.180 (2)	−0.0492 (4)	0.6414 (12)	0.011 (3)*	0.200 (7)
C6A	0.101 (2)	−0.1015 (6)	0.5499 (9)	0.007 (3)*	0.200 (7)
H6A	0.0292	−0.0900	0.4617	0.009*	0.200 (7)
C5A	0.129 (3)	−0.1687 (5)	0.5876 (14)	0.024 (5)*	0.200 (7)
H5A	0.0816	−0.2039	0.5234	0.028*	0.200 (7)
C4A	0.227 (2)	−0.1868 (5)	0.7210 (16)	0.020 (4)*	0.200 (7)
H4A	0.2377	−0.2335	0.7498	0.024*	0.200 (7)
C3A	0.303 (2)	−0.1361 (7)	0.8054 (11)	0.018 (4)*	0.200 (7)
H3A	0.3775	−0.1471	0.8930	0.022*	0.200 (7)
HW1A	0.016 (6)	0.3359 (17)	0.867 (2)	0.028*
HW1B	−0.099 (5)	0.3728 (13)	0.764 (4)	0.028*
HW2A	0.406 (6)	0.3418 (16)	0.5044 (19)	0.028*
HW2B	0.485 (5)	0.3815 (12)	0.600 (4)	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cr1	0.01435 (16)	0.00763 (14)	0.01064 (15)	0.0002 (2)	0.00028 (11)	0.0000 (2)
C11	0.0265 (17)	0.0098 (12)	0.0212 (14)	−0.0049 (11)	0.0168 (13)	−0.0041 (10)
C12	0.0276 (17)	0.0154 (15)	0.0190 (15)	0.0026 (12)	0.0138 (13)	0.0021 (12)
O11	0.0492 (16)	0.0181 (11)	0.0355 (14)	−0.0159 (10)	0.0257 (12)	−0.0135 (10)
O12	0.0499 (15)	0.0123 (10)	0.0273 (12)	0.0118 (10)	0.0205 (11)	0.0068 (9)
O14	0.0220 (11)	0.0174 (12)	0.0157 (10)	−0.0056 (9)	0.0036 (9)	−0.0046 (9)
O13	0.0271 (13)	0.0100 (11)	0.0181 (11)	0.0048 (8)	0.0071 (10)	0.0029 (8)
C21	0.0142 (13)	0.0143 (15)	0.0134 (13)	0.0026 (11)	0.0067 (10)	0.0014 (11)
C22	0.0155 (14)	0.0128 (14)	0.0167 (14)	−0.0029 (11)	0.0068 (11)	−0.0014 (11)
O22	0.0213 (12)	0.0118 (12)	0.0133 (10)	−0.0012 (8)	0.0029 (9)	−0.0013 (8)
O21	0.0150 (10)	0.0115 (11)	0.0126 (10)	0.0021 (8)	−0.0008 (8)	0.0015 (8)
O24	0.0332 (15)	0.0117 (12)	0.0247 (14)	0.0056 (9)	0.0147 (11)	0.0070 (8)
O23	0.0277 (13)	0.0115 (11)	0.0239 (13)	−0.0059 (9)	0.0121 (10)	−0.0076 (8)
OW1	0.0145 (12)	0.0110 (11)	0.0185 (12)	0.0034 (7)	0.0047 (10)	0.0008 (7)
OW2	0.0208 (14)	0.0133 (12)	0.0198 (12)	−0.0025 (7)	0.0031 (10)	−0.0011 (7)
N1	0.0254 (17)	0.0137 (14)	0.0246 (16)	−0.0009 (11)	0.0033 (13)	−0.0023 (11)
N2	0.0150 (15)	0.0179 (19)	0.0084 (13)	0.0007 (12)	−0.0013 (11)	0.0031 (12)
C1	0.016 (2)	0.0140 (14)	0.011 (2)	0.0005 (12)	0.0032 (15)	0.0028 (12)
C6	0.0124 (17)	0.020 (2)	0.0107 (16)	0.0040 (14)	−0.0026 (13)	−0.0003 (15)
C5	0.0127 (17)	0.024 (2)	0.0158 (18)	0.0029 (16)	−0.0016 (13)	−0.0073 (16)
C4	0.0159 (18)	0.0116 (14)	0.020 (2)	−0.0013 (14)	0.0019 (19)	−0.0036 (12)
C3	0.0151 (18)	0.0116 (17)	0.0193 (19)	−0.0014 (14)	0.0039 (14)	−0.0011 (14)

Geometric parameters (Å, º)

Cr1—O22	1.949 (2)	N2—C1	1.364 (4)
Cr1—O13	1.960 (2)	N2—H2	0.8800
Cr1—O14	1.962 (2)	C1—C6	1.402 (5)
Cr1—O21	1.963 (2)	C6—C5	1.363 (5)
Cr1—OW2	2.006 (3)	C6—H6	0.9500
Cr1—OW1	2.007 (3)	C5—C4	1.414 (5)
C11—O11	1.223 (4)	C5—H5	0.9500
C11—O14	1.285 (4)	C4—C3	1.337 (5)
C11—C12	1.545 (4)	C4—H4	0.9500
C12—O12	1.233 (4)	C3—H3	0.9500
C12—O13	1.285 (4)	N1A—C1A	1.331 (4)
C21—O24	1.214 (4)	N1A—H1A1	0.8800
C21—O21	1.283 (4)	N1A—H1A2	0.8800
C21—C22	1.545 (3)	N2A—C3A	1.359 (5)
C22—O23	1.253 (4)	N2A—C1A	1.363 (5)
C22—O22	1.278 (4)	N2A—H2A1	0.8800
OW1—HW1A	0.816 (18)	C1A—C6A	1.402 (5)
OW1—HW1B	0.796 (18)	C6A—C5A	1.363 (5)
OW2—HW2A	0.846 (18)	C6A—H6A	0.9500
OW2—HW2B	0.803 (18)	C5A—C4A	1.414 (6)
N1—C1	1.331 (3)	C5A—H5A	0.9500
N1—H1A	0.8800	C4A—C3A	1.337 (6)
N1—H1B	0.8800	C4A—H4A	0.9500
N2—C3	1.358 (4)	C3A—H3A	0.9500
O22—Cr1—O13	94.80 (11)	C3—N2—C1	122.9 (3)
O22—Cr1—O14	176.23 (12)	C3—N2—H2	118.6
O13—Cr1—O14	82.55 (9)	C1—N2—H2	118.6
O22—Cr1—O21	83.15 (7)	N1—C1—N2	117.3 (4)
O13—Cr1—O21	176.38 (11)	N1—C1—C6	125.5 (4)
O14—Cr1—O21	99.63 (11)	N2—C1—C6	117.2 (3)
O22—Cr1—OW2	88.05 (9)	C5—C6—C1	119.8 (3)
O13—Cr1—OW2	91.94 (10)	C5—C6—H6	120.1
O14—Cr1—OW2	89.36 (10)	C1—C6—H6	120.1
O21—Cr1—OW2	90.98 (10)	C6—C5—C4	121.1 (3)
O22—Cr1—OW1	93.02 (9)	C6—C5—H5	119.5
O13—Cr1—OW1	90.31 (10)	C4—C5—H5	119.5
O14—Cr1—OW1	89.68 (10)	C3—C4—C5	117.9 (3)
O21—Cr1—OW1	86.82 (9)	C3—C4—H4	121.0
OW2—Cr1—OW1	177.42 (14)	C5—C4—H4	121.0
O11—C11—O14	126.0 (4)	C4—C3—N2	121.1 (3)
O11—C11—C12	120.1 (3)	C4—C3—H3	119.4
O14—C11—C12	113.9 (3)	N2—C3—H3	119.4
O12—C12—O13	124.1 (3)	C1A—N1A—H1A1	120.0
O12—C12—C11	122.0 (3)	C1A—N1A—H1A2	120.0
O13—C12—C11	114.0 (3)	H1A1—N1A—H1A2	120.0
C11—O14—Cr1	114.8 (2)	C3A—N2A—C1A	122.7 (4)
C12—O13—Cr1	114.8 (2)	C3A—N2A—H2A1	118.6
O24—C21—O21	125.9 (3)	C1A—N2A—H2A1	118.6
O24—C21—C22	120.0 (4)	N1A—C1A—N2A	117.8 (5)
O21—C21—C22	114.1 (3)	N1A—C1A—C6A	125.0 (5)
O23—C22—O22	125.6 (4)	N2A—C1A—C6A	117.1 (3)
O23—C22—C21	120.2 (4)	C5A—C6A—C1A	120.0 (4)
O22—C22—C21	114.2 (3)	C5A—C6A—H6A	120.0
C22—O22—Cr1	114.4 (2)	C1A—C6A—H6A	120.0
C21—O21—Cr1	113.8 (2)	C6A—C5A—C4A	120.9 (4)
Cr1—OW1—HW1A	106 (3)	C6A—C5A—H5A	119.6
Cr1—OW1—HW1B	108 (3)	C4A—C5A—H5A	119.6
HW1A—OW1—HW1B	117 (3)	C3A—C4A—C5A	117.8 (4)
Cr1—OW2—HW2A	113 (3)	C3A—C4A—H4A	121.1
Cr1—OW2—HW2B	109 (3)	C5A—C4A—H4A	121.1
HW2A—OW2—HW2B	100 (3)	C4A—C3A—N2A	121.3 (4)
C1—N1—H1A	120.0	C4A—C3A—H3A	119.4
C1—N1—H1B	120.0	N2A—C3A—H3A	119.4
H1A—N1—H1B	120.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
OW1—HW1A···O23^i	0.82 (2)	1.86 (2)	2.660 (4)	166 (3)
OW1—HW1B···O11^ii	0.80 (2)	1.92 (2)	2.663 (3)	156 (4)
OW2—HW2A···O24^iii	0.85 (2)	1.78 (2)	2.621 (4)	172 (4)
OW2—HW2B···O12^iv	0.80 (2)	1.95 (2)	2.687 (3)	153 (4)
N1—H1A···O12^v	0.88	2.33	3.183 (5)	164
N1—H1B···O23	0.88	2.38	3.251 (4)	171
N2—H2···O13^v	0.88	2.02	2.865 (3)	159

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