Triethano­lammonium di­hydrogenphosphate

The structure of the title compound, [HN(C₂H₄OH)₃]⁺·H₂PO₄⁻ or C₆H₁₆NO₃⁺·H₂PO₄⁻, contains two distinct di­hydrogenphosphate anions and two triethano­l­ammonium cations in the asymmetric unit. The H₂PO₄ units are linked in a polymeric chain by strong P—OH...O—P hydrogen bonds along the [010] direction, while the (H₂PO₄)⁻ and [HN(C₂H₄OH)₃]⁺ ions are connected by O—H...O hydrogen bonds to yield sheet-like entities. The triethano­lammonium cation shows a tripodal conformation and the ammonium H atom forms an intramolecular trifurcated hydrogen bond with the O atoms of the three ethanol groups.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• H-atom completeness 96%
• R factor = 0.037
• wR factor = 0.084
• Data-to-parameter ratio = 16.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



FORMU_01  There is a discrepancy between the atom counts in the
          _chemical_formula_sum and the formula from the _atom_site* data.
          Atom count from _chemical_formula_sum:C6 H18 N1 O7 P1
          Atom count from the _atom_site data:  C6 H17.187 N1 O7 P1

CELLZ_01
         From the CIF: _cell_formula_units_Z    4
         From the CIF: _chemical_formula_sum  C6 H18 N O7 P
         TEST: Compare cell contents of formula and atom_site data

         atom    Z*formula  cif sites diff
         C         24.00     24.00    0.00
         H         72.00     68.75    3.25
         N          4.00      4.00    0.00
         O         28.00     28.00    0.00
         P          4.00      4.00    0.00
          Difference between formula and atom_site contents detected.
          WARNING: H atoms missing from atom site list. Is this intentional?

REFLT_03
         From the CIF: _diffrn_reflns_theta_max           30.08
         From the CIF: _reflns_number_total               4714
         Count of symmetry unique reflns         3496
         Completeness (_total/calc)            134.84%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      1218
         Fraction of Friedel pairs measured     0.348
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure

---

S1. Comment

Open-framework metal phosphates are generally synthesized under hydrothermal conditions in the presence of amine. The main role of the amine is to behave as a structure-directing agent and also a ligand to metal. Simple amine phosphates formed in the preparation of metal phosphates act as intermediates and sometimes occur as unexpected stable side products (Oliver et al., 1998; Neeraj et al., 1999). In the present study, we report the structure of triethanolammonium dihydrogenphosphate, (I).

The structure of (I) composed of two distinct dihydrogenphosphate anions and two triethanolammonium cations (Fig. 1). The N2-centered triethanolammonium cation is partially disordered over two positions [major component atoms C7, C9 and C11 with occupancy = 0.729 (4) and d_av(N—C) = 1.501 (3) Å; minor component atoms C7a, C9a and C11a with occupancy = 0.271 (4) and d_av(N—C) = 1.495 (9) Å]. The triethanolammonium cation exibits a tripodal conformation, in which the ammonium H atom forms an intramolecular trifurcated hydrogen bond with the O atoms of the three ethanol groups. Similar trifurcated intramolecular hydrogen bonds were observed in triethanolammonium bromide (Yilmaz et al., 1996). The bond geometry within the cation is comparable to those of other triethanolammonium salts with bromide (Yilmaz et al., 1996), hexachloroplatinate (Yilmaz et al., 1997), chloride and hydrogensulfide (Mootz et al., 1990).

The crystal structure contains an extensive network of O—H···O hydrogen bonds. The H₂PO₄ units are linked in a polymeric chain by triple hydrogen bonds involving the OH and P=O groups along the [010] direction (Fig. 2). The (H₂PO₄)⁻ and [HN(C₂H₄OH)₃]⁺ ions are also connected by O—H···O hydrogen bonds to yield sheet-like entities (Fig. 3). Within the sheet the H₂PO₄ anions are hydrogen bonded in pairs and bridged by the O—H_T···O_P (T = triethanolammonium, P = phosphate) type hydrogen bonds involving the ammonium ions. There is no hydrogen bonding between the neighboring sheets, which are held together by van der Waals interactions.

S2. Experimental

1.153 ml H₃PO₄ (17 mmol) (aqueous 85% wt) was added dropwise to a solution of triethanolamine (1.33 ml, 10 mmol) in 20 ml me thanol and stirred for 30 min at the room temperature. The resulting solution was kept at 343 K for a day. X-ray quality crystals were formed when the solution was cooled to room temperature. Colourless transparent crystals of the title compound were washed with metanol and dried in air.

S3. Refinement

Water, hydroxyl and amine H atoms were found in difference maps and were refined by riding in their as-found positions. H atoms bonded to C atoms were placed in calculated positions 0.97 Å from their parent atoms and modelled by riding.

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and ATOMS (Shape Software, 1999); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. View of (I) (50% displacement ellipsoids). H atoms are drawn as small spheres of arbitrary radii and H bonds are indicated by dashed lines. Only the major orientation (atoms C7, C9 and C11) of the N2-centred molecule is shown; all C—H H atoms have been omitted for clarity.
	Fig. 2. Details of the dihydrogen phosphate chain in (I), with hydrogen bonds indicated by dashed lines. Note how the P1 and P2 moieties are linked by alternating double and single hydrogen bonds. The symmetry codes are as in Table 2.
	Fig. 3. [010] projection of (I), showing the sheet-like arrangement of [HN(C2H4OH)3]^+ and (H2PO4)^− groups. Colour key: [H2PO4]^− tetrahedra yellow, O atoms red, C atoms blue, N atoms purple, H atoms grey. The H···O portions of the hydrogen bonds are highlighted in green. C—H hydrogen atoms have been omitted for clarity.

Triethanolammonium dihydrogenphosphate

Crystal data

C6H16NO3^+·H2PO4^−	F(000) = 528
Mr = 247.18	Dx = 1.507 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 14.1354 (7) Å	Cell parameters from 3525 reflections
b = 5.5364 (3) Å	θ = 2.6–28.1°
c = 15.5323 (7) Å	µ = 0.27 mm^−1
β = 116.354 (1)°	T = 293 K
V = 1089.21 (9) Å^3	Blade, colourless
Z = 4	0.45 × 0.12 × 0.04 mm

Data collection

Bruker SMART1000 CCD diffractometer	4714 independent reflections
Radiation source: fine-focus sealed tube	3779 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 30.1°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −19→19
Tmin = 0.885, Tmax = 0.989	k = −5→7
9297 measured reflections	l = −21→21

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: geom (C-H) and difmap (O-H and N-H)
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.0442P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
4714 reflections	Δρmax = 0.27 e Å^−3
284 parameters	Δρmin = −0.28 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.18 (8)

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	Occ. (<1)
P1	0.31964 (4)	0.61894 (11)	0.19862 (4)	0.02914 (14)
O1	0.39078 (13)	0.6776 (4)	0.15381 (12)	0.0444 (5)
O2	0.20379 (12)	0.6632 (3)	0.13789 (11)	0.0361 (4)
O3	0.34045 (13)	0.3471 (3)	0.22959 (13)	0.0435 (4)
H1	0.3051	0.2888	0.2548	0.052*
O4	0.35691 (12)	0.7616 (4)	0.29626 (11)	0.0392 (4)
H2	0.3119	0.8784	0.2883	0.047*
P2	0.11319 (4)	0.03585 (11)	0.26504 (4)	0.02875 (13)
O5	0.06599 (13)	0.0792 (4)	0.33259 (12)	0.0462 (5)
O6	0.22771 (11)	0.1089 (3)	0.30189 (11)	0.0351 (4)
O7	0.09954 (13)	−0.2409 (3)	0.23909 (12)	0.0351 (4)
H3	0.1369	−0.2633	0.2125	0.042*
O8	0.05059 (13)	0.1729 (4)	0.16759 (12)	0.0430 (5)
H4	0.0044	0.1029	0.1274	0.052*
N1	0.31374 (13)	0.5765 (4)	0.57448 (12)	0.0302 (4)
H5	0.3088	0.4160	0.5844	0.036*
C1	0.33789 (19)	0.5967 (5)	0.48965 (17)	0.0372 (6)
H6	0.2727	0.5902	0.4306	0.045*
H7	0.3718	0.7503	0.4917	0.045*
C2	0.40896 (18)	0.3947 (5)	0.49126 (17)	0.0366 (5)
H8	0.4217	0.4045	0.4349	0.044*
H9	0.4763	0.4091	0.5478	0.044*
C3	0.2107 (2)	0.6867 (6)	0.5578 (2)	0.0464 (7)
H10	0.2092	0.8536	0.5383	0.056*
H11	0.2045	0.6856	0.6176	0.056*
C4	0.11798 (19)	0.5546 (6)	0.48212 (18)	0.0455 (7)
H12	0.0529	0.6121	0.4816	0.055*
H13	0.1147	0.5841	0.4193	0.055*
C5	0.4043 (2)	0.6722 (6)	0.66384 (17)	0.0476 (7)
H14	0.3974	0.8458	0.6672	0.057*
H15	0.4703	0.6392	0.6611	0.057*
C6	0.4060 (2)	0.5565 (7)	0.75234 (17)	0.0532 (9)
H16	0.4682	0.6099	0.8085	0.064*
H17	0.3443	0.6072	0.7596	0.064*
O9	0.36237 (14)	0.1699 (4)	0.49249 (13)	0.0452 (5)
H18	0.3121	0.1557	0.4320	0.054*
O10	0.12986 (14)	0.3044 (4)	0.50272 (13)	0.0491 (5)
H19	0.1083	0.2354	0.4491	0.059*
O11	0.40698 (14)	0.3044 (4)	0.74634 (13)	0.0499 (5)
H20	0.4750	0.2682	0.7771	0.060*
N2	0.77358 (13)	0.6721 (4)	0.09932 (13)	0.0287 (4)
H21	0.7905	0.8318	0.1073	0.034*
C7	0.8556 (2)	0.5487 (7)	0.0803 (2)	0.0346 (8)	0.729 (4)
H22	0.8305	0.3885	0.0553	0.041*	0.729 (4)
H23	0.9186	0.5296	0.1406	0.041*	0.729 (4)
C7A	0.7996 (7)	0.5685 (18)	0.0243 (7)	0.035 (2)*	0.271 (4)
C8	0.8844 (2)	0.6789 (6)	0.01109 (19)	0.0449 (7)
H24	0.9518	0.6197	0.0174	0.054*
H25	0.8316	0.6472	−0.0540	0.054*
C9	0.6647 (2)	0.6513 (6)	0.0138 (2)	0.0326 (8)	0.729 (4)
H26	0.6721	0.6583	−0.0454	0.039*	0.729 (4)
H27	0.6339	0.4964	0.0160	0.039*	0.729 (4)
C9A	0.6690 (6)	0.6448 (18)	0.0876 (6)	0.033 (2)*	0.271 (4)
C10	0.59535 (18)	0.8423 (6)	0.01397 (19)	0.0445 (7)
H28	0.5305	0.8368	−0.0454	0.053*
H29	0.5775	0.8176	0.0668	0.053*
C11	0.7711 (2)	0.5870 (7)	0.1893 (2)	0.0385 (9)	0.729 (4)
H30	0.7788	0.4127	0.1940	0.046*	0.729 (4)
H31	0.7037	0.6281	0.1879	0.046*	0.729 (4)
C11A	0.8546 (7)	0.569 (2)	0.2008 (7)	0.041 (2)*	0.271 (4)
C12	0.8604 (2)	0.7047 (7)	0.27677 (19)	0.0502 (8)
H32	0.8506	0.6738	0.3338	0.060*
H33	0.9276	0.6362	0.2867	0.060*
O12	0.89125 (13)	0.9323 (4)	0.02875 (12)	0.0397 (4)
H34	0.8572	1.0170	−0.0158	0.048*
O13	0.64238 (14)	1.0691 (4)	0.02313 (12)	0.0433 (5)
H35	0.6260	1.1010	−0.0411	0.052*
O14	0.86032 (14)	0.9570 (4)	0.26128 (14)	0.0499 (5)
H36	0.9251	1.0007	0.2909	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0308 (3)	0.0271 (3)	0.0288 (3)	−0.0023 (3)	0.0127 (2)	−0.0009 (3)
O1	0.0465 (9)	0.0522 (13)	0.0391 (9)	−0.0169 (9)	0.0232 (8)	−0.0076 (9)
O2	0.0363 (8)	0.0370 (11)	0.0296 (8)	0.0011 (8)	0.0097 (6)	−0.0044 (7)
O3	0.0434 (9)	0.0282 (11)	0.0644 (12)	0.0026 (8)	0.0290 (9)	0.0069 (9)
O4	0.0363 (8)	0.0429 (12)	0.0299 (8)	0.0078 (8)	0.0069 (7)	−0.0050 (8)
P2	0.0294 (2)	0.0292 (3)	0.0270 (3)	−0.0041 (3)	0.0120 (2)	−0.0037 (3)
O5	0.0450 (9)	0.0563 (14)	0.0458 (9)	−0.0140 (9)	0.0280 (8)	−0.0183 (9)
O6	0.0316 (7)	0.0318 (9)	0.0391 (8)	−0.0055 (8)	0.0133 (6)	−0.0030 (8)
O7	0.0387 (9)	0.0268 (10)	0.0436 (9)	−0.0060 (8)	0.0217 (7)	−0.0047 (8)
O8	0.0450 (9)	0.0369 (12)	0.0359 (9)	−0.0014 (9)	0.0078 (7)	0.0009 (8)
N1	0.0342 (9)	0.0227 (11)	0.0298 (9)	−0.0001 (8)	0.0107 (7)	−0.0006 (8)
C1	0.0459 (12)	0.0313 (14)	0.0360 (11)	−0.0010 (12)	0.0197 (10)	0.0067 (11)
C2	0.0351 (11)	0.0381 (14)	0.0361 (12)	−0.0005 (12)	0.0155 (10)	−0.0027 (11)
C3	0.0443 (14)	0.0411 (16)	0.0529 (15)	0.0091 (13)	0.0207 (12)	−0.0025 (13)
C4	0.0366 (12)	0.055 (2)	0.0421 (14)	0.0069 (14)	0.0150 (11)	0.0013 (14)
C5	0.0457 (14)	0.0424 (18)	0.0405 (14)	−0.0076 (13)	0.0062 (11)	−0.0119 (13)
C6	0.0467 (14)	0.075 (3)	0.0307 (13)	0.0113 (17)	0.0106 (11)	−0.0107 (15)
O9	0.0520 (10)	0.0313 (11)	0.0428 (9)	0.0029 (9)	0.0123 (8)	−0.0002 (8)
O10	0.0566 (11)	0.0531 (14)	0.0347 (9)	−0.0145 (11)	0.0177 (8)	−0.0060 (9)
O11	0.0387 (9)	0.0624 (15)	0.0483 (11)	0.0070 (10)	0.0192 (8)	0.0112 (11)
N2	0.0298 (8)	0.0251 (11)	0.0336 (9)	−0.0020 (8)	0.0161 (7)	−0.0012 (8)
C7	0.0347 (15)	0.0308 (18)	0.0432 (18)	0.0104 (15)	0.0217 (14)	0.0056 (15)
C8	0.0461 (14)	0.0498 (19)	0.0483 (15)	0.0062 (14)	0.0295 (12)	−0.0009 (14)
C9	0.0282 (14)	0.0269 (19)	0.0372 (17)	−0.0049 (14)	0.0095 (12)	−0.0091 (14)
C10	0.0299 (11)	0.057 (2)	0.0416 (14)	−0.0006 (13)	0.0110 (10)	0.0043 (14)
C11	0.0373 (16)	0.043 (2)	0.0401 (17)	−0.0012 (17)	0.0215 (14)	0.0082 (17)
C12	0.0454 (15)	0.071 (2)	0.0329 (13)	−0.0002 (15)	0.0159 (11)	0.0083 (14)
O12	0.0391 (9)	0.0427 (12)	0.0300 (8)	−0.0048 (8)	0.0088 (7)	0.0087 (8)
O13	0.0526 (10)	0.0373 (12)	0.0380 (9)	0.0044 (9)	0.0184 (8)	−0.0018 (8)
O14	0.0377 (9)	0.0608 (15)	0.0508 (11)	−0.0054 (10)	0.0193 (8)	−0.0100 (10)

Geometric parameters (Å, º)

P1—O1	1.4907 (17)	C6—H17	0.9700
P1—O2	1.5034 (16)	O9—H18	0.8945
P1—O3	1.567 (2)	O10—H19	0.8405
P1—O4	1.5787 (17)	O11—H20	0.8856
O3—H1	0.8250	N2—C9A	1.414 (8)
O4—H2	0.8768	N2—C7	1.484 (3)
P2—O5	1.4915 (16)	N2—C7A	1.484 (9)
P2—O6	1.5129 (15)	N2—C11	1.491 (3)
P2—O8	1.5688 (18)	N2—C9	1.527 (3)
P2—O7	1.5740 (17)	N2—C11A	1.587 (10)
O7—H3	0.8117	N2—H21	0.9100
O8—H4	0.7768	C7—C8	1.493 (4)
N1—C3	1.492 (3)	C7—H22	0.9700
N1—C1	1.505 (3)	C7—H23	0.9700
N1—C5	1.506 (3)	C8—O12	1.425 (4)
N1—H5	0.9100	C8—H24	0.9700
C1—C2	1.496 (4)	C8—H25	0.9700
C1—H6	0.9700	C9—C10	1.443 (4)
C1—H7	0.9700	C9—H26	0.9700
C2—O9	1.412 (3)	C9—H27	0.9700
C2—H8	0.9700	C10—O13	1.398 (4)
C2—H9	0.9700	C10—H28	0.9700
C3—C4	1.506 (4)	C10—H29	0.9700
C3—H10	0.9700	C11—C12	1.530 (4)
C3—H11	0.9700	C11—H30	0.9700
C4—O10	1.414 (4)	C11—H31	0.9700
C4—H12	0.9700	C12—O14	1.418 (4)
C4—H13	0.9700	C12—H32	0.9700
C5—C6	1.507 (4)	C12—H33	0.9700
C5—H14	0.9700	O12—H34	0.7968
C5—H15	0.9700	O13—H35	0.9347
C6—O11	1.399 (4)	O14—H36	0.8568
C6—H16	0.9700
O1—P1—O2	116.37 (10)	C4—O10—H19	105.5
O1—P1—O3	106.18 (11)	C6—O11—H20	103.3
O2—P1—O3	110.66 (10)	C9A—N2—C7	142.1 (4)
O1—P1—O4	109.45 (10)	C9A—N2—C7A	117.8 (5)
O2—P1—O4	109.10 (9)	C9A—N2—C11	68.2 (4)
O3—P1—O4	104.39 (10)	C7—N2—C11	112.8 (2)
P1—O3—H1	116.8	C7A—N2—C11	137.0 (4)
P1—O4—H2	108.7	C7—N2—C9	111.5 (2)
O5—P2—O6	115.37 (9)	C7A—N2—C9	78.1 (4)
O5—P2—O8	111.35 (11)	C11—N2—C9	111.0 (2)
O6—P2—O8	106.63 (10)	C9A—N2—C11A	110.0 (5)
O5—P2—O7	107.12 (11)	C7—N2—C11A	75.4 (4)
O6—P2—O7	110.24 (10)	C7A—N2—C11A	108.6 (5)
O8—P2—O7	105.73 (10)	C9—N2—C11A	147.3 (4)
P2—O7—H3	104.2	C9A—N2—H21	108.5
P2—O8—H4	116.5	C7—N2—H21	107.1
C3—N1—C1	113.68 (19)	C7A—N2—H21	109.9
C3—N1—C5	112.4 (2)	C11—N2—H21	107.1
C1—N1—C5	110.54 (19)	C9—N2—H21	107.1
C3—N1—H5	106.6	C11A—N2—H21	100.6
C1—N1—H5	106.6	N2—C7—C8	114.1 (3)
C5—N1—H5	106.6	N2—C7—H22	108.7
C2—C1—N1	110.0 (2)	C8—C7—H22	108.7
C2—C1—H6	109.7	N2—C7—H23	108.7
N1—C1—H6	109.7	C8—C7—H23	108.7
C2—C1—H7	109.7	H22—C7—H23	107.6
N1—C1—H7	109.7	O12—C8—C7	110.7 (2)
H6—C1—H7	108.2	O12—C8—H24	109.5
O9—C2—C1	110.2 (2)	C7—C8—H24	109.5
O9—C2—H8	109.6	O12—C8—H25	109.5
C1—C2—H8	109.6	C7—C8—H25	109.5
O9—C2—H9	109.6	H24—C8—H25	108.1
C1—C2—H9	109.6	C10—C9—N2	111.5 (2)
H8—C2—H9	108.1	C10—C9—H26	109.3
N1—C3—C4	112.4 (2)	N2—C9—H26	109.3
N1—C3—H10	109.1	C10—C9—H27	109.3
C4—C3—H10	109.1	N2—C9—H27	109.3
N1—C3—H11	109.1	H26—C9—H27	108.0
C4—C3—H11	109.1	O13—C10—C9	111.4 (2)
H10—C3—H11	107.9	O13—C10—H28	109.3
O10—C4—C3	108.9 (2)	C9—C10—H28	109.3
O10—C4—H12	109.9	O13—C10—H29	109.3
C3—C4—H12	109.9	C9—C10—H29	109.3
O10—C4—H13	109.9	H28—C10—H29	108.0
C3—C4—H13	109.9	N2—C11—C12	110.1 (2)
H12—C4—H13	108.3	N2—C11—H30	109.6
N1—C5—C6	110.8 (2)	C12—C11—H30	109.6
N1—C5—H14	109.5	N2—C11—H31	109.6
C6—C5—H14	109.5	C12—C11—H31	109.6
N1—C5—H15	109.5	H30—C11—H31	108.2
C6—C5—H15	109.5	O14—C12—C11	109.3 (2)
H14—C5—H15	108.1	O14—C12—H32	109.8
O11—C6—C5	111.1 (2)	C11—C12—H32	109.8
O11—C6—H16	109.4	O14—C12—H33	109.8
C5—C6—H16	109.4	C11—C12—H33	109.8
O11—C6—H17	109.4	H32—C12—H33	108.3
C5—C6—H17	109.4	C8—O12—H34	116.7
H16—C6—H17	108.0	C10—O13—H35	100.3
C2—O9—H18	102.8	C12—O14—H36	105.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O6	0.82	1.85	2.670 (2)	170
O4—H2···O6^i	0.88	1.82	2.680 (2)	166
O7—H3···O2^ii	0.81	1.84	2.642 (2)	171
O8—H4···O12^iii	0.78	1.90	2.681 (2)	180
N1—H5···O9	0.91	2.33	2.818 (3)	113
N1—H5···O10	0.91	2.35	2.774 (3)	108
N1—H5···O11	0.91	2.35	2.830 (3)	113
O9—H18···O6	0.89	1.85	2.738 (2)	170
O10—H19···O5	0.84	1.85	2.690 (2)	178
O11—H20···O1^iv	0.89	1.79	2.671 (2)	175
N2—H21···O14	0.91	2.25	2.754 (3)	114
N2—H21···O12	0.91	2.32	2.768 (2)	110
N2—H21···O13	0.91	2.32	2.779 (3)	111
O12—H34···O2^v	0.80	1.88	2.655 (2)	163
O13—H35···O1^v	0.93	1.71	2.644 (2)	173
O14—H36···O5^vi	0.86	1.85	2.698 (2)	169

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