Bis(l-threoninium) sulfate monohydrate

Sridhar, B.; Srinivasan, N.; Rajaram, R.K.

doi:10.1107/S1600536801008960

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Bis(L-threoninium) sulfate monohydrate

B. Sridhar, N. Srinivasan and R. K. Rajaram

In the title compound, 2C₄H₁₀NO₃⁺·SO₄²⁻·H₂O, both threoninium molecules have a gauche II form for the C^γ and gauche I form for the O^γ. The sulfate anion links the cation in an infinite manner through hydrogen bonds along the b and c axes. The two water molecules on the twofold axes link the sulfate groups and one of the cations.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801008960/ob6047sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801008960/ob6047Isup2.hkl Contains datablock I

CCDC reference: 170759

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.032
wR factor = 0.094
Data-to-parameter ratio = 8.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.97
         From the CIF: _reflns_number_total               1732
         Count of symmetry unique reflns         1468
         Completeness (_total/calc)            117.98%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       264
         Fraction of Friedel pairs measured     0.180
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure

Comment top

Threonine is the isometric form of amino acids containing more than one asymmetric C atom. The crystal structures of DL-threonine (Shoemaker et al., 1950), L-threonine (Shoemaker et al., 1950) and L-allothreonine (Swaminathan & Srinivasan, 1975) have been reported. In the present study, threonine complex with sulfuric acid, (I), has been investigated.

The geometries of the L-threoninium cations A and B are as expected (Fig. 1 and Table 1). In cation A, the O1A—C11—C12—N11 and O1B—C11—C12—N11 torsion angles are -12.6 (4) and 167.9 (3)°, respectively, and the corresponding torsion angles in B are -8.3 (4) and 172.1 (3)°. This tendency towards non-planarity is also found in various amino acids (Lakshiminarayanan et al., 1967). The side-chain conformation is given by the torsion angles about C^α—C^β, giving the orientation of the γ atom with respect to N (Lakshiminarayanan et al., 1967). These angles are close to 60, 180 and 300°. In the present case, the C^γ atom moves to a gauche II form [-49.2 (4) and -48.1 (4)°] and the O^γ atom to a gauche I form [75.8 (3) and 78.6 (3)°] for both molecules.

The sulfate anion forms hydrogen bonds with threoninium molecules A and B (Fig. 2 and Table 2). Threonium molecule A is engaged in a three-centred zigzag (Z1) head-to-tail sequence with N11—H11C···O1A(-x + 1/2, y + 1/2, -z + 2) and N11—H11C···O2A(-x + 1/2, y - 1/2, -z + 2) hydrogen bonds connecting 2₁-related amino acids (Vijayan, 1988). The O^γ atom of threoninium molecule A, as acceptor, links the carboxyl O atom of threoninium molecule B through a strong hydrogen bond, O2B—H2B···O1C(x, y + 1, z). The two water molecules, lying on the twofold axes, link (i) the sulfate groups and (ii) threoninium molecule B through the O2C atom. One of the water molecules, as acceptor, links the amino group of threoninum molecule B, N21—H21B···OW1(x, y, 1 + z). Two bifurcated hydrogen bonds are observed for the N21 amino group with sulfate O atoms through H21A and H21C. A four-centre hydrogen bond is observed in the case of N11—H11C involving the sulfate O atom and the double-bonded O atom of the carboxyl group of both molecules, connecting all the moieties in the structure (Jeffrey & Saengar, 1991). The sulfate anion links through the N11 atom of three threoninium A molecules, resulting in infinite chains along the b axis. The O3 atom of the sulfate anion links the N21 atoms of two threoninium B molecules, resulting in infinite chains along the c axis.

Experimental top

Crystals of (I) were obtained from an aqueous solution of a 2:1 stoichiometric ratio of L-threonine and sulfuric acid.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. Views of the two independent threonine cations showing the atomic numbering scheme and 50% probability displacement ellipsoids (Johnson, 1976).
	Fig. 2. Packing diagram of the molecule viewed down the b axis.

Bis(L-threoninium) sulfate monohydrate top

Crystal data top

2C₄H₁₀NO₃⁺·SO₄²⁻·H₂O	F(000) = 752
M_r = 354.34	D_x = 1.551 Mg m⁻³ D_m = 1.54 Mg m⁻³ D_m measured by floatation in carbon tetrachloride and xylene
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 23.096 (4) Å	Cell parameters from 25 reflections
b = 6.281 (9) Å	θ = 10.8–14.4°
c = 11.648 (1) Å	µ = 0.27 mm⁻¹
β = 116.122 (9)°	T = 293 K
V = 1517 (2) Å³	Needles, colorless
Z = 4	0.5 × 0.45 × 0.33 mm

Data collection top

Enraf-Nonius sealed tube diffractometer	1675 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.018
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
ω–2θ scans	h = −1→27
Absorption correction: ψ scan (North et al., 1968)	k = −1→7
T_min = 0.869, T_max = 0.914	l = −13→12
1872 measured reflections	25 standard reflections every 3 reflections
1732 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.0764P)² + 1.0496P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.094	(Δ/σ)_max < 0.001
S = 0.98	Δρ_max = 0.26 e Å⁻³
1732 reflections	Δρ_min = −0.32 e Å⁻³
213 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.026 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: (Flack, 1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.07 (10)

Crystal data top

2C₄H₁₀NO₃⁺·SO₄²⁻·H₂O	V = 1517 (2) Å³
M_r = 354.34	Z = 4
Monoclinic, C2	Mo Kα radiation
a = 23.096 (4) Å	µ = 0.27 mm⁻¹
b = 6.281 (9) Å	T = 293 K
c = 11.648 (1) Å	0.5 × 0.45 × 0.33 mm
β = 116.122 (9)°

Data collection top

Enraf-Nonius sealed tube diffractometer	1675 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.018
T_min = 0.869, T_max = 0.914	25 standard reflections every 3 reflections
1872 measured reflections	intensity decay: none
1732 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.094	Δρ_max = 0.26 e Å⁻³
S = 0.98	Δρ_min = −0.32 e Å⁻³
1732 reflections	Absolute structure: (Flack, 1983)
213 parameters	Absolute structure parameter: −0.07 (10)
1 restraint

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
S1	0.12376 (3)	0.18012 (12)	0.15518 (6)	0.0233 (2)
O1	0.10142 (10)	0.0461 (4)	0.0385 (2)	0.0393 (6)
O2	0.07958 (10)	0.1482 (4)	0.21372 (19)	0.0335 (5)
O3	0.12167 (11)	0.4041 (4)	0.1165 (2)	0.0406 (6)
O4	0.18916 (10)	0.1178 (5)	0.2433 (2)	0.0394 (6)
O1A	0.23195 (10)	0.0417 (5)	0.9916 (2)	0.0380 (6)
O1B	0.13354 (9)	0.1455 (4)	0.85151 (19)	0.0335 (5)
H1B	0.1222	0.0820	0.8997	0.050*
C11	0.19592 (13)	0.1223 (5)	0.8917 (2)	0.0251 (6)
C12	0.21886 (11)	0.2074 (5)	0.7972 (2)	0.0231 (6)
H12	0.2024	0.3527	0.7739	0.028*
N11	0.29024 (10)	0.2174 (4)	0.8618 (2)	0.0250 (6)
H11A	0.3046	0.2679	0.8077	0.038*
H11B	0.3061	0.0874	0.8870	0.038*
H11C	0.3029	0.3027	0.9295	0.038*
C13	0.19350 (13)	0.0731 (6)	0.6746 (3)	0.0282 (7)
H13	0.1471	0.0999	0.6276	0.034*
C14	0.22416 (16)	0.1343 (7)	0.5879 (3)	0.0428 (9)
H14A	0.2072	0.0455	0.5132	0.064*
H14B	0.2700	0.1153	0.6328	0.064*
H14C	0.2147	0.2806	0.5629	0.064*
O1C	0.20185 (9)	−0.1482 (4)	0.7063 (2)	0.0339 (5)
H1C	0.2380	−0.1857	0.7178	0.051*
O2A	0.12088 (9)	0.6655 (5)	0.87761 (17)	0.0368 (6)
O2B	0.09874 (9)	0.6397 (5)	0.67159 (17)	0.0354 (6)
H2B	0.1312	0.7129	0.6926	0.053*
C21	0.08573 (12)	0.6159 (5)	0.7699 (2)	0.0250 (6)
C22	0.02032 (13)	0.5186 (5)	0.7319 (2)	0.0237 (6)
H22	0.0174	0.3858	0.6855	0.028*
N21	0.01341 (11)	0.4693 (5)	0.8498 (2)	0.0265 (6)
H21A	−0.0252	0.4121	0.8289	0.040*
H21B	0.0173	0.5885	0.8939	0.040*
H21C	0.0439	0.3776	0.8975	0.040*
C23	−0.03193 (12)	0.6721 (6)	0.6437 (2)	0.0290 (6)
H23	−0.0309	0.6685	0.5606	0.035*
O2C	−0.01522 (11)	0.8823 (4)	0.6921 (2)	0.0398 (6)
H2C	−0.0383	0.9195	0.7255	0.060*
C24	−0.09955 (14)	0.6109 (9)	0.6208 (3)	0.0492 (10)
H24A	−0.1297	0.7127	0.5645	0.074*
H24B	−0.1022	0.6090	0.7008	0.074*
H24C	−0.1096	0.4721	0.5825	0.074*
OW1	0.0000	0.7880 (6)	0.0000	0.0318 (7)
HW1	0.0343 (19)	0.847 (11)	0.019 (4)	0.067 (15)*
OW2	0.0000	0.1407 (8)	0.5000	0.106 (3)
HW2	−0.012 (4)	0.053 (13)	0.543 (6)	0.13 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0237 (3)	0.0195 (4)	0.0307 (3)	0.0005 (3)	0.0156 (3)	0.0009 (3)
O1	0.0383 (11)	0.0466 (17)	0.0423 (12)	−0.0143 (12)	0.0262 (10)	−0.0136 (12)
O2	0.0383 (10)	0.0290 (14)	0.0444 (10)	0.0009 (11)	0.0284 (9)	0.0024 (11)
O3	0.0420 (12)	0.0239 (13)	0.0589 (14)	−0.0011 (10)	0.0250 (11)	0.0106 (12)
O4	0.0319 (10)	0.0403 (15)	0.0422 (11)	0.0073 (11)	0.0128 (9)	0.0029 (12)
O1A	0.0312 (10)	0.0454 (16)	0.0347 (11)	−0.0037 (11)	0.0119 (9)	0.0138 (11)
O1B	0.0271 (9)	0.0359 (15)	0.0430 (10)	0.0045 (10)	0.0205 (8)	0.0105 (11)
C11	0.0266 (12)	0.0192 (15)	0.0298 (13)	−0.0007 (12)	0.0126 (11)	0.0002 (12)
C12	0.0201 (11)	0.0210 (15)	0.0272 (12)	0.0005 (12)	0.0094 (10)	0.0027 (13)
N11	0.0223 (10)	0.0245 (15)	0.0259 (10)	−0.0039 (10)	0.0084 (9)	−0.0044 (10)
C13	0.0208 (12)	0.0336 (18)	0.0273 (13)	−0.0001 (13)	0.0081 (10)	0.0012 (14)
C14	0.0505 (17)	0.052 (3)	0.0280 (13)	−0.0107 (19)	0.0192 (13)	−0.0017 (17)
O1C	0.0270 (10)	0.0276 (13)	0.0495 (12)	−0.0050 (10)	0.0189 (10)	−0.0086 (11)
O2A	0.0308 (10)	0.0447 (16)	0.0258 (9)	−0.0122 (12)	0.0041 (8)	0.0016 (12)
O2B	0.0318 (10)	0.0467 (17)	0.0317 (9)	−0.0134 (11)	0.0177 (8)	−0.0043 (11)
C21	0.0248 (12)	0.0206 (14)	0.0282 (13)	0.0023 (12)	0.0104 (10)	0.0012 (12)
C22	0.0251 (13)	0.0240 (15)	0.0231 (12)	−0.0025 (12)	0.0117 (10)	−0.0042 (12)
N21	0.0279 (12)	0.0255 (14)	0.0257 (11)	−0.0008 (11)	0.0115 (9)	0.0042 (10)
C23	0.0251 (12)	0.0384 (18)	0.0228 (12)	−0.0009 (15)	0.0101 (10)	0.0040 (15)
O2C	0.0450 (13)	0.0289 (13)	0.0573 (14)	0.0063 (12)	0.0333 (12)	0.0070 (12)
C24	0.0230 (13)	0.070 (3)	0.0469 (16)	−0.0018 (18)	0.0087 (12)	0.019 (2)
OW1	0.0289 (15)	0.0262 (17)	0.0417 (17)	0.000	0.0169 (14)	0.000
OW2	0.240 (8)	0.030 (3)	0.087 (3)	0.000	0.106 (5)	0.000

Geometric parameters (Å, º) top

S1—O4	1.457 (2)	O1C—H1C	0.8200
S1—O2	1.4692 (19)	O2A—C21	1.197 (3)
S1—O3	1.471 (3)	O2B—C21	1.314 (3)
S1—O1	1.485 (2)	O2B—H2B	0.8200
O1A—C11	1.204 (4)	C21—C22	1.504 (4)
O1B—C11	1.312 (3)	C22—N21	1.484 (3)
O1B—H1B	0.8200	C22—C23	1.533 (4)
C11—C12	1.515 (4)	C22—H22	0.9800
C12—N11	1.482 (3)	N21—H21A	0.8900
C12—C13	1.535 (4)	N21—H21B	0.8900
C12—H12	0.9800	N21—H21C	0.8900
N11—H11A	0.8900	C23—O2C	1.420 (5)
N11—H11B	0.8900	C23—C24	1.514 (4)
N11—H11C	0.8900	C23—H23	0.9800
C13—O1C	1.429 (5)	O2C—H2C	0.8200
C13—C14	1.516 (4)	C24—H24A	0.9600
C13—H13	0.9800	C24—H24B	0.9600
C14—H14A	0.9600	C24—H24C	0.9600
C14—H14B	0.9600	OW1—HW1	0.81 (5)
C14—H14C	0.9600	OW2—HW2	0.86 (7)

O4—S1—O2	110.68 (13)	H14B—C14—H14C	109.5
O4—S1—O3	110.88 (16)	C13—O1C—H1C	109.5
O2—S1—O3	109.68 (14)	C21—O2B—H2B	109.5
O4—S1—O1	109.09 (15)	O2A—C21—O2B	125.0 (3)
O2—S1—O1	108.37 (13)	O2A—C21—C22	122.9 (2)
O3—S1—O1	108.07 (17)	O2B—C21—C22	112.0 (2)
C11—O1B—H1B	109.5	N21—C22—C21	108.4 (2)
O1A—C11—O1B	125.1 (3)	N21—C22—C23	112.2 (2)
O1A—C11—C12	122.5 (2)	C21—C22—C23	109.5 (3)
O1B—C11—C12	112.4 (2)	N21—C22—H22	108.9
N11—C12—C11	108.2 (2)	C21—C22—H22	108.9
N11—C12—C13	112.3 (2)	C23—C22—H22	108.9
C11—C12—C13	111.7 (3)	C22—N21—H21A	109.5
N11—C12—H12	108.2	C22—N21—H21B	109.5
C11—C12—H12	108.2	H21A—N21—H21B	109.5
C13—C12—H12	108.2	C22—N21—H21C	109.5
C12—N11—H11A	109.5	H21A—N21—H21C	109.5
C12—N11—H11B	109.5	H21B—N21—H21C	109.5
H11A—N11—H11B	109.5	O2C—C23—C24	112.7 (3)
C12—N11—H11C	109.5	O2C—C23—C22	108.8 (2)
H11A—N11—H11C	109.5	C24—C23—C22	113.9 (3)
H11B—N11—H11C	109.5	O2C—C23—H23	107.0
O1C—C13—C14	111.7 (3)	C24—C23—H23	107.0
O1C—C13—C12	109.9 (2)	C22—C23—H23	107.0
C14—C13—C12	112.4 (3)	C23—O2C—H2C	109.5
O1C—C13—H13	107.5	C23—C24—H24A	109.5
C14—C13—H13	107.5	C23—C24—H24B	109.5
C12—C13—H13	107.5	H24A—C24—H24B	109.5
C13—C14—H14A	109.5	C23—C24—H24C	109.5
C13—C14—H14B	109.5	H24A—C24—H24C	109.5
H14A—C14—H14B	109.5	H24B—C24—H24C	109.5
C13—C14—H14C	109.5	HW1—OW1—HW1ⁱ	125.5 (9)
H14A—C14—H14C	109.5	HW2—OW2—HW2ⁱⁱ	101.0 (10)

O1A—C11—C12—N11	−12.6 (4)	O2A—C21—C22—N21	−8.3 (4)
O1B—C11—C12—N11	167.9 (3)	O2B—C21—C22—N21	172.1 (3)
O1A—C11—C12—C13	111.5 (3)	O2A—C21—C22—C23	114.4 (3)
O1B—C11—C12—C13	−68.0 (3)	O2B—C21—C22—C23	−65.2 (3)
N11—C12—C13—O1C	75.8 (3)	N21—C22—C23—O2C	78.6 (3)
C11—C12—C13—O1C	−46.0 (3)	C21—C22—C23—O2C	−41.9 (3)
N11—C12—C13—C14	−49.2 (4)	N21—C22—C23—C24	−48.1 (4)
C11—C12—C13—C14	−171.0 (3)	C21—C22—C23—C24	−168.5 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1B···O1ⁱⁱⁱ	0.82	1.89	2.666 (3)	157
N11—H11A···O4^iv	0.89	2.30	2.927 (5)	128
N11—H11B···O3^v	0.89	2.04	2.761 (4)	137
N11—H11C···O1A^vi	0.89	2.10	2.846 (4)	141
N11—H11C···O2A^vii	0.89	2.33	2.837 (3)	117
N11—H11C···O1^iv	0.89	2.58	3.052 (4)	114
O1C—H1C···O4^v	0.82	1.97	2.746 (3)	157
O2B—H2B···O1C^viii	0.82	1.79	2.600 (3)	167
N21—H21A···O2ⁱⁱ	0.89	2.01	2.797 (4)	148
N21—H21A···O3ⁱⁱ	0.89	2.57	3.337 (3)	144
N21—H21B···OW1ⁱⁱⁱ	0.89	1.92	2.764 (4)	157
N21—H21C···O3ⁱⁱⁱ	0.89	2.39	3.038 (3)	130
N21—H21C···O1ⁱⁱⁱ	0.89	2.62	3.477 (5)	161
O2C—H2C···O2^ix	0.82	2.02	2.764 (3)	151
OW1—HW1···O1^viii	0.81 (5)	1.93 (5)	2.719 (3)	165 (6)
OW2—HW2···O2C^x	0.86 (7)	2.07 (7)	2.908 (4)	162 (7)

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

Experimental details

Crystal data
Chemical formula	2C₄H₁₀NO₃⁺·SO₄²⁻·H₂O
M_r	354.34
Crystal system, space group	Monoclinic, C2
Temperature (K)	293
a, b, c (Å)	23.096 (4), 6.281 (9), 11.648 (1)
β (°)	116.122 (9)
V (Å³)	1517 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.5 × 0.45 × 0.33

Data collection
Diffractometer	Enraf-Nonius sealed tube diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.869, 0.914
No. of measured, independent and observed [I > 2σ(I)] reflections	1872, 1732, 1675
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.094, 0.98
No. of reflections	1732
No. of parameters	213
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.32
Absolute structure	(Flack, 1983)
Absolute structure parameter	−0.07 (10)

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1999), SHELXL97.

Selected torsion angles (º) top

O1A—C11—C12—N11	−12.6 (4)	O2A—C21—C22—N21	−8.3 (4)
N11—C12—C13—O1C	75.8 (3)	N21—C22—C23—O2C	78.6 (3)
N11—C12—C13—C14	−49.2 (4)	N21—C22—C23—C24	−48.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1B···O1ⁱ	0.82	1.89	2.666 (3)	157.0
N11—H11A···O4ⁱⁱ	0.89	2.30	2.927 (5)	127.6
N11—H11B···O3ⁱⁱⁱ	0.89	2.04	2.761 (4)	137.0
N11—H11C···O1A^iv	0.89	2.10	2.846 (4)	141.3
N11—H11C···O2A^v	0.89	2.33	2.837 (3)	116.5
N11—H11C···O1ⁱⁱ	0.89	2.58	3.052 (4)	114.3
O1C—H1C···O4ⁱⁱⁱ	0.82	1.97	2.746 (3)	157.2
O2B—H2B···O1C^vi	0.82	1.79	2.600 (3)	167.3
N21—H21A···O2^vii	0.89	2.01	2.797 (4)	147.6
N21—H21A···O3^vii	0.89	2.57	3.337 (3)	144.3
N21—H21B···OW1ⁱ	0.89	1.92	2.764 (4)	157.3
N21—H21C···O3ⁱ	0.89	2.39	3.038 (3)	129.5
N21—H21C···O1ⁱ	0.89	2.62	3.477 (5)	161.4
O2C—H2C···O2^viii	0.82	2.02	2.764 (3)	151.1
OW1—HW1···O1^vi	0.81 (5)	1.93 (5)	2.719 (3)	165 (6)
OW2—HW2···O2C^ix	0.86 (7)	2.07 (7)	2.908 (4)	162 (7)

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

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