2,6-Diethyl­anilinium dihydrogen phosphate–phospho­ric acid (1/1)

Khemiri, H.; Akriche, S.T.; Al-Deyab, S.S.; Rzaigui, M.

doi:10.1107/S1600536810051159

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o101

https://doi.org/10.1107/S1600536810051159

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2,6-Diethylanilinium dihydrogen phosphate–phosphoric acid (1/1)

Hamed Khemiri,^a Samah Toumi Akriche,^a ^* Salem S. Al-Deyab ^b and Mohamed Rzaigui ^a

^aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia, and ^bPetrochemical Research Chair, College of Science, King Saud University Ryadh, Saudi Arabia
^*Correspondence e-mail: toumiakriche@yahoo.fr

(Received 30 November 2010; accepted 6 December 2010; online 11 December 2010)

In the crystal structure of the title salt, C₁₀H₁₆N⁺·H₂PO₄⁻·H₃PO₄, the H₂PO₄⁻ and H₃PO₄ components are connected into infinite chains extending along the b-axis direction by way of O—H⋯O links. These chains are also linked through O—H⋯O hydrogen bonds thus building up a supramolecular two-dimensional framework extending parallel to (001). The organic cations cross-link the anionic layers by way of multiple N—H⋯O interactions, leading to a cohesive network.

Related literature

For hydrogen bonds, see: Blessing (1986 ); Desiraju (1995 ). For their biological occurence, see: Richards et al. (1972 ); Perutz & Ten Eyck (1972 ). For related structures with phosphoric acid, see: Belam et al. (2005 ); Mighell et al. (1969 ); Smith et al. (1955 ). For related organic cations, see: Akriche & Rzaigui (2008 ); Smirani Sta et al. (2010 ).

Experimental

Crystal data

C₁₀H₁₆N⁺·H₂O₄P⁻·H₃O₄P
M_r = 345.22
Monoclinic, P 2₁ /c
a = 8.1634 (10) Å
b = 7.707 (2) Å
c = 25.680 (6) Å
β = 102.686 (19)°
V = 1576.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 293 K
0.45 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer
5173 measured reflections
2776 independent reflections
2417 reflections with I > 2σ(I)
R_int = 0.011
2 standard reflections every 120 min intensity decay: 4%

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.104
S = 1.06
2776 reflections
198 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	1.84	2.540 (2)	142
O3—H3⋯O8ⁱⁱ	0.82	1.72	2.520 (2)	166
O4—H4⋯O7ⁱⁱⁱ	0.82	1.74	2.521 (2)	158
O5—H5⋯O1	0.82	1.86	2.664 (2)	165
O6—H6⋯O7ⁱⁱ	0.82	1.76	2.577 (2)	171
N1—H1A⋯O6	0.89	2.18	2.927 (2)	141
N1—H1B⋯O8^iv	0.89	1.89	2.772 (2)	172
N1—H1C⋯O2	0.89	1.98	2.861 (3)	168
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810051159/dn2632sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051159/dn2632Isup2.hkl

checkCIF report

Comment top

The H₃PO₄ molecules play an important role for structure cohesion of adduct materials, by connecting the other components of crystal by a network of hydrogen bonds particularly strong (Desiraju, 1995; Blessing, 1986). Such hydrogen bonds are of interest because of their widespread biological occurrence. For example, hydrogen bonds between phosphate groups and histidyl, imidazolyl groups are involved in the active-site substrate-binding mechanism of ribonuclease (Richards et al., 1972) and in the regulation of the oxygen affinity of deoxyhemoglobin by 2,3-diphosphoglycerate (Perutz et al., 1972). The influence of the hydrogen bond scheme on the building of supramolecular anionic packing for the title compound is discussed with regard to other adduct phosphates.

The asymmetric unit of (I) consists of two phosphoric entities (H₂PO₄^- and H₃PO₄) and one 2,6-diethylanilinium organic cation (Fig. 1). A view of the structure projected along the b direction (Fig. 2) shows that inorganic layers are built by H₂PO₄^- anions and H₃PO₄ molecules. Via O2—H2···O1 and O6—H6···O7 intermolecular hydrogen bonds, each phosphoric entity form a corrugated chain extending along the b-axis. These undulating chains are further linked through O3—H3···O8, O4—H4···O7 and O5—H5···O1 hydrogen bonds with short distances varying between 1.72 and 1.86 Å (Table 1), thus building up an extended supramolecular two-dimensional framework parallel to the ab plane. This topology is slightly different from that of (C₆H₁₄N)H₂PO₄H₃PO₄ (Belam et al., 2005) adduct one, where the H₂PO₄^- anions and H₃PO₄ molecules are connected alternatively by O—H···O hydrogen bonds to form infinite corrugated chains parallel to the c direction.

It is also useful to compare the geometrical parameters of phosphoric entities in the title compound and in the crystallized H₃PO₄ (Mighell et al., 1969; Smith et al., 1955). This comparison does not show significant differences that could be generated by the organic molecule in the provided geometric properties of these species. The 2,6-diethylanilinium cations are pendant on both the faces of the two-dimensional inorganic sheet by establishing intermolecular N—H···O hydrogen bonds thanks to the NH₃⁺ group. Among the three hydrogen atoms of the ammonium group only one, establishes a hydrogen bond with the H₃PO₄ molecule. The remaining ones are connected to oxygen atoms of H₂PO₄^- anions.

The geometrical hydrogen bonding scheme are given in Table 1. Examination of geometrical features of the organic entity shows that bond lengths and angles exhibit no deviations from the usually values observed in others related 2,6-diethylanilinium structures (C₁₀H₁₆N)ClO₄ (Smirani Sta et al., 2010) and (C₁₀H₁₆N)₂H₂P₂O₇.2H₂O (Akriche et al., 2008).

Related literature top

For hydrogen bonds, see: Blessing (1986); Desiraju (1995). For their biological occurence, see: Richards et al. (1972); Perutz et al. (1972). For related phosphoric structures, see: Belam et al. (2005); Mighell et al. (1969); Smith et al. (1955). For related organic cations, see: Akriche & Rzaigui (2008); Smirani Sta et al. (2010).

Experimental top

A solution of orthophosphoric acid (0,50 mmol in 30 ml of water) was added drop by drop to an ethanolic solution (5 ml) of 2,6-diethylaniline (2,488 mmol in 5 ml of ethanol). The so-obtained solution is kept in a sealed tube for three days and then submitted to a slow evaporation until the formation of good quality crystals, stable under normal conditions of temperature and moisture.

Structure description top

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bonds are represented as dashed lines.
	Fig. 2. Projection of (I) along the a axis. The H-atoms not involved in H-bonding are omitted. H bonds are shown as dashed lines.

2,6-Diethylanilinium dihydrogen phosphate–phosphoric acid (1/1) top

Crystal data top

C₁₀H₁₆N⁺·H₂O₄P⁻·H₃O₄P	F(000) = 728
M_r = 345.22	D_x = 1.455 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.1634 (10) Å	θ = 9–11°
b = 7.707 (2) Å	µ = 0.31 mm⁻¹
c = 25.680 (6) Å	T = 293 K
β = 102.686 (19)°	Prism, colourless
V = 1576.2 (6) Å³	0.45 × 0.30 × 0.20 mm
Z = 4

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	R_int = 0.011
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 2.6°
Graphite monochromator	h = −9→9
non–profiled ω scans	k = −9→0
5173 measured reflections	l = −30→26
2776 independent reflections	2 standard reflections every 120 min
2417 reflections with I > 2σ(I)	intensity decay: 4%

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0631P)² + 0.6675P] where P = (F_o² + 2F_c²)/3
2776 reflections	(Δ/σ)_max = 0.001
198 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₀H₁₆N⁺·H₂O₄P⁻·H₃O₄P	V = 1576.2 (6) Å³
M_r = 345.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1634 (10) Å	µ = 0.31 mm⁻¹
b = 7.707 (2) Å	T = 293 K
c = 25.680 (6) Å	0.45 × 0.30 × 0.20 mm
β = 102.686 (19)°

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	R_int = 0.011
5173 measured reflections	2 standard reflections every 120 min
2776 independent reflections	intensity decay: 4%
2417 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	Δρ_max = 0.27 e Å⁻³
2776 reflections	Δρ_min = −0.47 e Å⁻³
198 parameters

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
P1	0.89551 (6)	0.42643 (7)	0.69762 (2)	0.02954 (17)
P2	0.57483 (6)	0.63702 (6)	0.78754 (2)	0.02854 (16)
O1	0.90841 (18)	0.36241 (19)	0.75328 (6)	0.0396 (4)
O2	0.9067 (2)	0.6272 (2)	0.69495 (7)	0.0520 (5)
H2	0.9850	0.6616	0.7184	0.078*
O3	0.72469 (17)	0.39370 (19)	0.65968 (6)	0.0391 (4)
H3	0.6783	0.3113	0.6706	0.059*
O4	1.0255 (2)	0.3435 (3)	0.67058 (7)	0.0600 (5)
H4	1.1176	0.3437	0.6913	0.090*
O5	0.69580 (18)	0.48369 (19)	0.80976 (6)	0.0388 (4)
H5	0.7548	0.4612	0.7886	0.058*
O6	0.49043 (19)	0.59476 (19)	0.72822 (6)	0.0387 (4)
H6	0.4372	0.5041	0.7269	0.058*
O7	0.66900 (17)	0.80396 (18)	0.78532 (7)	0.0400 (4)
O8	0.44861 (18)	0.63937 (18)	0.82220 (6)	0.0379 (4)
N1	0.6019 (2)	0.8023 (2)	0.64703 (7)	0.0376 (4)
H1A	0.5247	0.7406	0.6585	0.056*
H1B	0.5939	0.9133	0.6558	0.056*
H1C	0.7036	0.7626	0.6621	0.056*
C1	0.5743 (3)	0.7867 (3)	0.58854 (9)	0.0389 (5)
C2	0.4324 (3)	0.7015 (3)	0.56111 (10)	0.0469 (6)
C3	0.4120 (4)	0.6914 (3)	0.50585 (11)	0.0575 (7)
H3A	0.3183	0.6356	0.4856	0.069*
C4	0.5292 (4)	0.7631 (4)	0.48074 (10)	0.0613 (7)
H4A	0.5136	0.7546	0.4439	0.074*
C5	0.6679 (4)	0.8466 (3)	0.50942 (10)	0.0555 (7)
H5A	0.7453	0.8938	0.4917	0.067*
C6	0.6953 (3)	0.8624 (3)	0.56494 (9)	0.0452 (6)
C7	0.3079 (4)	0.6215 (4)	0.59107 (12)	0.0626 (7)
H7A	0.3650	0.5291	0.6136	0.075*
H7B	0.2783	0.7095	0.6144	0.075*
C8	0.1485 (4)	0.5490 (5)	0.55760 (15)	0.0829 (10)
H8A	0.0873	0.6398	0.5362	0.124*
H8B	0.0812	0.5013	0.5804	0.124*
H8C	0.1750	0.4594	0.5348	0.124*
C9	0.8439 (4)	0.9572 (4)	0.59828 (11)	0.0589 (7)
H9A	0.8011	1.0495	0.6173	0.071*
H9B	0.9036	0.8768	0.6248	0.071*
C10	0.9693 (4)	1.0357 (5)	0.56996 (13)	0.0706 (8)
H10A	1.0219	0.9453	0.5537	0.106*
H10B	1.0532	1.0977	0.5952	0.106*
H10C	0.9128	1.1143	0.5429	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0263 (3)	0.0247 (3)	0.0378 (3)	0.00059 (19)	0.0075 (2)	0.0007 (2)
P2	0.0267 (3)	0.0179 (3)	0.0428 (3)	0.00200 (18)	0.0113 (2)	0.0022 (2)
O1	0.0415 (8)	0.0350 (8)	0.0435 (8)	0.0127 (6)	0.0116 (7)	0.0082 (6)
O2	0.0617 (11)	0.0258 (9)	0.0574 (11)	−0.0121 (7)	−0.0108 (8)	0.0056 (7)
O3	0.0319 (8)	0.0319 (8)	0.0508 (9)	−0.0057 (6)	0.0033 (7)	0.0076 (7)
O4	0.0376 (9)	0.0916 (15)	0.0514 (10)	0.0181 (9)	0.0113 (7)	−0.0113 (10)
O5	0.0412 (8)	0.0293 (8)	0.0496 (9)	0.0141 (6)	0.0182 (7)	0.0093 (7)
O6	0.0469 (9)	0.0261 (8)	0.0437 (8)	−0.0069 (6)	0.0111 (7)	0.0043 (6)
O7	0.0295 (7)	0.0216 (7)	0.0689 (10)	−0.0021 (6)	0.0105 (7)	0.0031 (7)
O8	0.0375 (8)	0.0277 (8)	0.0533 (9)	0.0065 (6)	0.0203 (7)	0.0026 (7)
N1	0.0473 (10)	0.0293 (9)	0.0390 (10)	0.0005 (8)	0.0154 (8)	0.0022 (7)
C1	0.0564 (13)	0.0247 (10)	0.0368 (11)	0.0084 (9)	0.0130 (10)	0.0011 (8)
C2	0.0609 (14)	0.0301 (12)	0.0472 (13)	0.0067 (11)	0.0065 (11)	0.0013 (10)
C3	0.0760 (18)	0.0397 (14)	0.0497 (15)	0.0056 (13)	−0.0014 (13)	−0.0045 (11)
C4	0.101 (2)	0.0459 (15)	0.0362 (13)	0.0114 (15)	0.0134 (14)	−0.0023 (11)
C5	0.0851 (19)	0.0433 (14)	0.0443 (14)	0.0056 (13)	0.0279 (13)	0.0005 (11)
C6	0.0645 (15)	0.0335 (12)	0.0421 (12)	0.0054 (10)	0.0215 (11)	0.0010 (10)
C7	0.0640 (17)	0.0617 (18)	0.0573 (16)	−0.0121 (14)	0.0027 (13)	0.0002 (13)
C8	0.074 (2)	0.079 (2)	0.089 (2)	−0.0143 (18)	0.0033 (18)	−0.0070 (19)
C9	0.0748 (18)	0.0567 (16)	0.0522 (15)	−0.0140 (14)	0.0290 (13)	−0.0032 (12)
C10	0.077 (2)	0.077 (2)	0.0653 (18)	−0.0115 (17)	0.0303 (15)	0.0042 (16)

Geometric parameters (Å, º) top

P1—O1	1.4937 (16)	C2—C7	1.532 (4)
P1—O4	1.5296 (16)	C3—C4	1.381 (4)
P1—O3	1.5364 (15)	C3—H3A	0.9300
P1—O2	1.5525 (17)	C4—C5	1.368 (4)
P2—O8	1.5022 (15)	C4—H4A	0.9300
P2—O7	1.5063 (15)	C5—C6	1.399 (3)
P2—O6	1.5622 (16)	C5—H5A	0.9300
P2—O5	1.5652 (14)	C6—C9	1.511 (4)
O2—H2	0.8200	C7—C8	1.501 (4)
O3—H3	0.8200	C7—H7A	0.9700
O4—H4	0.8200	C7—H7B	0.9700
O5—H5	0.8200	C8—H8A	0.9600
O6—H6	0.8200	C8—H8B	0.9600
N1—C1	1.474 (3)	C8—H8C	0.9600
N1—H1A	0.8900	C9—C10	1.507 (4)
N1—H1B	0.8900	C9—H9A	0.9700
N1—H1C	0.8900	C9—H9B	0.9700
C1—C2	1.382 (3)	C10—H10A	0.9600
C1—C6	1.395 (3)	C10—H10B	0.9600
C2—C3	1.394 (4)	C10—H10C	0.9600

O1—P1—O4	112.72 (10)	C5—C4—H4A	119.6
O1—P1—O3	114.58 (9)	C3—C4—H4A	119.6
O4—P1—O3	105.49 (10)	C4—C5—C6	121.2 (3)
O1—P1—O2	112.27 (10)	C4—C5—H5A	119.4
O4—P1—O2	110.04 (12)	C6—C5—H5A	119.4
O3—P1—O2	100.93 (9)	C1—C6—C5	115.9 (2)
O8—P2—O7	115.74 (9)	C1—C6—C9	120.9 (2)
O8—P2—O6	111.54 (9)	C5—C6—C9	123.2 (2)
O7—P2—O6	105.11 (9)	C8—C7—C2	116.7 (3)
O8—P2—O5	104.66 (8)	C8—C7—H7A	108.1
O7—P2—O5	111.86 (9)	C2—C7—H7A	108.1
O6—P2—O5	107.82 (9)	C8—C7—H7B	108.1
P1—O2—H2	109.5	C2—C7—H7B	108.1
P1—O3—H3	109.5	H7A—C7—H7B	107.3
P1—O4—H4	109.5	C7—C8—H8A	109.5
P2—O5—H5	109.5	C7—C8—H8B	109.5
P2—O6—H6	109.5	H8A—C8—H8B	109.5
C1—N1—H1A	109.5	C7—C8—H8C	109.5
C1—N1—H1B	109.5	H8A—C8—H8C	109.5
H1A—N1—H1B	109.5	H8B—C8—H8C	109.5
C1—N1—H1C	109.5	C10—C9—C6	117.8 (2)
H1A—N1—H1C	109.5	C10—C9—H9A	107.8
H1B—N1—H1C	109.5	C6—C9—H9A	107.8
C2—C1—C6	124.9 (2)	C10—C9—H9B	107.8
C2—C1—N1	118.8 (2)	C6—C9—H9B	107.8
C6—C1—N1	116.4 (2)	H9A—C9—H9B	107.2
C1—C2—C3	116.4 (2)	C9—C10—H10A	109.5
C1—C2—C7	120.6 (2)	C9—C10—H10B	109.5
C3—C2—C7	123.0 (2)	H10A—C10—H10B	109.5
C4—C3—C2	120.8 (3)	C9—C10—H10C	109.5
C4—C3—H3A	119.6	H10A—C10—H10C	109.5
C2—C3—H3A	119.6	H10B—C10—H10C	109.5
C5—C4—C3	120.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.84	2.540 (2)	142
O3—H3···O8ⁱⁱ	0.82	1.72	2.520 (2)	166
O4—H4···O7ⁱⁱⁱ	0.82	1.74	2.521 (2)	158
O5—H5···O1	0.82	1.86	2.664 (2)	165
O6—H6···O7ⁱⁱ	0.82	1.76	2.577 (2)	171
N1—H1A···O6	0.89	2.18	2.927 (2)	141
N1—H1B···O8^iv	0.89	1.89	2.772 (2)	172
N1—H1C···O2	0.89	1.98	2.861 (3)	168

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+2, y−1/2, −z+3/2; (iv) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₆N⁺·H₂O₄P⁻·H₃O₄P
M_r	345.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.1634 (10), 7.707 (2), 25.680 (6)
β (°)	102.686 (19)
V (Å³)	1576.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.45 × 0.30 × 0.20

Data collection
Diffractometer	Enraf–Nonius TurboCAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5173, 2776, 2417
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.104, 1.06
No. of reflections	2776
No. of parameters	198
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.47

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.84	2.540 (2)	141.7
O3—H3···O8ⁱⁱ	0.82	1.72	2.520 (2)	165.9
O4—H4···O7ⁱⁱⁱ	0.82	1.74	2.521 (2)	158.3
O5—H5···O1	0.82	1.86	2.664 (2)	164.7
O6—H6···O7ⁱⁱ	0.82	1.76	2.577 (2)	171.2
N1—H1A···O6	0.89	2.18	2.927 (2)	140.8
N1—H1B···O8^iv	0.89	1.89	2.772 (2)	172.3
N1—H1C···O2	0.89	1.98	2.861 (3)	168.2

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+2, y−1/2, −z+3/2; (iv) −x+1, y+1/2, −z+3/2.

References

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