Morpholinium styphnate

Kalaivani, D.; Malarvizhi, R.

doi:10.1107/S1600536810038304

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2698

https://doi.org/10.1107/S1600536810038304

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Morpholinium styphnate

D. Kalaivani ^a ^* and R. Malarvizhi ^a

^aPG & Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli 620 002, Tamil Nadu, India
^*Correspondence e-mail: kalaivbalaj@yahoo.co.in

(Received 18 September 2010; accepted 25 September 2010; online 2 October 2010)

In the title molecular salt (systematic name: morpholinium 3-hydroxy-2,4,6-trinitrophenolate), C₄H₁₀NO⁺·C₆H₂N₃O₈⁻, two of the nitro groups of the anion are close to parallel with the plane of the benzene ring [dihedral angles = 3.46 (9) and 11.60 (10)°] and one is almost perpendicular [dihedral angle = 82.23 (8)°]. An intramolecular O—H⋯O hydrogen bond occurs in the anion. The morpholinium cation has a slightly distorted chair conformation. In the crystal, the components are linked by simple N—H⋯O and trifurcated N—H⋯(O,O,O) hydrogen bonds.

Related literature

For related molecular salts, see: Radha et al. (1987 ).

Experimental

Crystal data

C₄H₁₀NO⁺·C₆H₂N₃O₈⁻
M_r = 332.24
Triclinic, $[P \overline 1]$
a = 7.680 (5) Å
b = 7.973 (5) Å
c = 11.852 (5) Å
α = 94.785 (5)°
β = 99.016 (5)°
γ = 108.188 (5)°
V = 674.1 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 293 K
0.30 × 0.16 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.957, T_max = 0.977
16214 measured reflections
3841 independent reflections
2944 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.157
S = 1.06
3841 reflections
225 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯O5	0.91 (3)	1.75 (3)	2.571 (2)	149 (2)
N4—H4A⋯O7	0.87 (2)	1.87 (2)	2.715 (2)	164 (2)
N4—H4B⋯O2ⁱ	0.86 (2)	2.31 (2)	2.962 (2)	132.4 (17)
N4—H4B⋯O5ⁱⁱ	0.86 (2)	2.42 (2)	2.967 (2)	121.5 (17)
N4—H4B⋯O3ⁱⁱⁱ	0.86 (2)	2.54 (2)	3.206 (3)	134.3 (17)
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y, -z; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810038304/hb5640sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810038304/hb5640Isup2.hkl

checkCIF report

Comment top

Picric acid (1-hydroxy – 2,4,6- trinitrobenzene) forms 1:1 donor –acceptor adducts with amines and in these adducts, the main stabilizing factor is the proton transfer from OH of nitro compound to the nitrogen atom of amine (Radha et al.,1987). Unlike picric acid, styphnic acid (2,4,6-trinitro -1,3-benzene diol) contains two phenolic OH groups and hence the type of adduct formation with amines and the mode of interaction are to be envisaged. This necessitates the synthesis of the title molecule from styphnic acid and morpholine (tetrahydro – 1,4-oxazine). Single crystal X-ray analysis data clearly indicate that 1:1 adduct (Scheme 1)is formed from styphnic acid and morpholine and the main contributing factor for the formation of the adduct is the proton transfer from phenolic OH of styphnic acid to the nitrogen atom of morpholine. Hydrogen bond (N—H···O) is noticed between cation and anion moieties. Intramolecular hydrogen bond [O—H···O; R₁¹(6) motif] is also observed. Puckering parameters[(q2 = 0.0243(0.0017), q3=0.5764 (0.0019), φ2=-175.98(5.69), QT=0.5770(0.0019);θ2=2.41(0.17)] of the cation moiety (morpholinium ion) indicate that it has slightly distorted chair conformation.

Related literature top

For related molecular salts, see: Radha et al. (1987).

Experimental top

Styphnic acid (2.45 g, 0.01 mol) was dissolved in the minimum quantity of ethanol. Morpholine(0.90 g, 0.01 mol) dissolved in the minimum amount of ethanol was added to styphnic acid solution. The mixture was stirred well for 3 h and kept as such for another 6 h. The mixture was then poured into ice cold water with stirring. The adduct formed was filtered and washed first with water and then with alcohol and dried. The dried adduct was washed several times with ether and recrystallized from ethanol (yield 70–75% mp.481–483 K). Yellow prisms of (I) were obtained by slow evaporation of ethanol at room temperature. The same product was obtained when styphnic acid (0.01 mol) was mixed with excess morpholine (0.03 mol).

Structure description top

For related molecular salts, see: Radha et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) showing 50% displecement ellipsoids.
	Fig. 2. The hydrogen bonding pattern
	Fig. 3. The packing view of the adduct

morpholinium 3-hydroxy-2,4,6-trinitrophenolate top

Crystal data top

C₄H₁₀NO⁺·C₆H₂N₃O₈⁻	Z = 2
M_r = 332.24	F(000) = 344
Triclinic, P1	D_x = 1.637 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.680 (5) Å	Cell parameters from 5851 reflections
b = 7.973 (5) Å	θ = 1.8–29.8°
c = 11.852 (5) Å	µ = 0.15 mm⁻¹
α = 94.785 (5)°	T = 293 K
β = 99.016 (5)°	Prism, yellow
γ = 108.188 (5)°	0.30 × 0.16 × 0.16 mm
V = 674.1 (7) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	3841 independent reflections
Radiation source: fine-focus sealed tube	2944 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω and φ scan	θ_max = 29.8°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −10→10
T_min = 0.957, T_max = 0.977	k = −11→11
16214 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.157	w = 1/[σ²(F_o²) + (0.0867P)² + 0.1583P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3841 reflections	Δρ_max = 0.77 e Å⁻³
225 parameters	Δρ_min = −0.38 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.049 (7)

Crystal data top

C₄H₁₀NO⁺·C₆H₂N₃O₈⁻	γ = 108.188 (5)°
M_r = 332.24	V = 674.1 (7) Å³
Triclinic, P1	Z = 2
a = 7.680 (5) Å	Mo Kα radiation
b = 7.973 (5) Å	µ = 0.15 mm⁻¹
c = 11.852 (5) Å	T = 293 K
α = 94.785 (5)°	0.30 × 0.16 × 0.16 mm
β = 99.016 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3841 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2944 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.977	R_int = 0.023
16214 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.77 e Å⁻³
3841 reflections	Δρ_min = −0.38 e Å⁻³
225 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
C1	0.48003 (18)	0.27015 (18)	−0.13460 (12)	0.0293 (3)
C2	0.31234 (18)	0.11938 (18)	−0.14972 (11)	0.0287 (3)
C3	0.24207 (17)	0.02930 (17)	−0.06486 (12)	0.0270 (3)
C4	0.33875 (18)	0.09746 (17)	0.05024 (11)	0.0274 (3)
C5	0.49948 (18)	0.24441 (18)	0.07302 (12)	0.0288 (3)
C6	0.57105 (17)	0.32628 (17)	−0.01487 (12)	0.0278 (3)
C7	0.7665 (3)	0.2429 (2)	−0.41273 (15)	0.0457 (4)
H7A	0.7022	0.1253	−0.3954	0.055*
H7B	0.8644	0.2344	−0.4533	0.055*
C8	0.6313 (3)	0.3086 (3)	−0.48707 (15)	0.0497 (4)
H8A	0.5789	0.2278	−0.5589	0.060*
H8B	0.5298	0.3097	−0.4479	0.060*
C9	0.7903 (3)	0.6028 (3)	−0.40700 (17)	0.0536 (5)
H9A	0.6880	0.6021	−0.3681	0.064*
H9B	0.8454	0.7225	−0.4244	0.064*
C10	0.9345 (2)	0.5533 (2)	−0.32858 (15)	0.0453 (4)
H10A	1.0405	0.5600	−0.3652	0.054*
H10B	0.9784	0.6355	−0.2571	0.054*
N1	0.74511 (16)	0.47391 (16)	0.01785 (11)	0.0332 (3)
N2	0.21517 (18)	0.0548 (2)	−0.26913 (11)	0.0398 (3)
N3	0.27441 (17)	0.01490 (17)	0.14458 (11)	0.0352 (3)
N4	0.84911 (19)	0.36922 (19)	−0.30416 (11)	0.0373 (3)
O1	0.81876 (17)	0.54823 (17)	−0.05681 (12)	0.0544 (4)
O2	0.81128 (17)	0.52044 (18)	0.12078 (11)	0.0533 (3)
O3	0.1114 (3)	0.1265 (3)	−0.31268 (14)	0.0847 (6)
O4	0.2437 (3)	−0.0695 (3)	−0.31820 (14)	0.0838 (6)
O5	0.14855 (16)	−0.13353 (15)	0.12339 (10)	0.0440 (3)
O6	0.3436 (2)	0.0883 (2)	0.24304 (10)	0.0587 (4)
O7	0.53339 (16)	0.33703 (18)	−0.21939 (10)	0.0463 (3)
O8	0.08817 (14)	−0.11441 (14)	−0.09399 (10)	0.0371 (3)
O9	0.7206 (2)	0.4823 (2)	−0.51108 (10)	0.0534 (3)
H4A	0.762 (3)	0.371 (3)	−0.2657 (19)	0.053 (6)*
H4B	0.931 (3)	0.333 (3)	−0.2646 (18)	0.047 (5)*
H5	0.562 (3)	0.285 (3)	0.1470 (19)	0.048 (5)*
H8	0.079 (4)	−0.160 (3)	−0.026 (2)	0.069 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0251 (6)	0.0320 (6)	0.0319 (7)	0.0093 (5)	0.0077 (5)	0.0079 (5)
C2	0.0269 (6)	0.0312 (6)	0.0266 (6)	0.0088 (5)	0.0033 (5)	0.0025 (5)
C3	0.0242 (6)	0.0244 (6)	0.0323 (7)	0.0082 (5)	0.0050 (5)	0.0033 (5)
C4	0.0273 (6)	0.0269 (6)	0.0288 (6)	0.0088 (5)	0.0066 (5)	0.0067 (5)
C5	0.0273 (6)	0.0283 (6)	0.0297 (7)	0.0090 (5)	0.0030 (5)	0.0033 (5)
C6	0.0221 (5)	0.0250 (6)	0.0352 (7)	0.0065 (5)	0.0045 (5)	0.0049 (5)
C7	0.0533 (9)	0.0447 (9)	0.0365 (8)	0.0164 (7)	0.0019 (7)	0.0028 (7)
C8	0.0473 (9)	0.0627 (11)	0.0332 (8)	0.0175 (8)	−0.0039 (7)	0.0003 (7)
C9	0.0680 (12)	0.0471 (10)	0.0506 (10)	0.0233 (9)	0.0134 (9)	0.0136 (8)
C10	0.0451 (9)	0.0448 (9)	0.0385 (8)	0.0042 (7)	0.0080 (7)	0.0061 (7)
N1	0.0245 (5)	0.0284 (6)	0.0452 (7)	0.0076 (4)	0.0049 (5)	0.0047 (5)
N2	0.0351 (6)	0.0491 (8)	0.0297 (6)	0.0079 (5)	0.0050 (5)	0.0014 (5)
N3	0.0343 (6)	0.0384 (6)	0.0337 (6)	0.0106 (5)	0.0084 (5)	0.0124 (5)
N4	0.0343 (6)	0.0486 (8)	0.0272 (6)	0.0108 (6)	0.0046 (5)	0.0101 (5)
O1	0.0419 (6)	0.0498 (7)	0.0578 (8)	−0.0079 (5)	0.0139 (6)	0.0147 (6)
O2	0.0385 (6)	0.0535 (7)	0.0484 (7)	−0.0044 (5)	−0.0036 (5)	−0.0010 (6)
O3	0.0871 (12)	0.1311 (16)	0.0459 (8)	0.0682 (12)	−0.0171 (8)	−0.0025 (9)
O4	0.1088 (14)	0.0908 (13)	0.0509 (9)	0.0491 (11)	−0.0020 (9)	−0.0255 (8)
O5	0.0432 (6)	0.0382 (6)	0.0473 (7)	0.0038 (5)	0.0130 (5)	0.0167 (5)
O6	0.0635 (8)	0.0691 (9)	0.0290 (6)	0.0013 (7)	0.0071 (5)	0.0107 (6)
O7	0.0364 (6)	0.0621 (8)	0.0379 (6)	0.0070 (5)	0.0117 (5)	0.0204 (5)
O8	0.0320 (5)	0.0316 (5)	0.0389 (6)	−0.0003 (4)	0.0047 (4)	0.0040 (4)
O9	0.0640 (8)	0.0711 (9)	0.0337 (6)	0.0321 (7)	0.0077 (5)	0.0185 (6)

Geometric parameters (Å, º) top

C1—O7	1.2426 (17)	C8—H8B	0.9700
C1—C2	1.4356 (19)	C9—O9	1.416 (2)
C1—C6	1.446 (2)	C9—C10	1.503 (3)
C2—C3	1.3665 (19)	C9—H9A	0.9700
C2—N2	1.4603 (19)	C9—H9B	0.9700
C3—O8	1.3378 (17)	C10—N4	1.482 (2)
C3—C4	1.4194 (19)	C10—H10A	0.9700
C4—C5	1.3817 (19)	C10—H10B	0.9700
C4—N3	1.4214 (17)	N1—O1	1.2203 (17)
C5—C6	1.3719 (19)	N1—O2	1.2233 (18)
C5—H5	0.91 (2)	N2—O3	1.197 (2)
C6—N1	1.4498 (18)	N2—O4	1.203 (2)
C7—N4	1.484 (2)	N3—O6	1.2184 (18)
C7—C8	1.502 (3)	N3—O5	1.2482 (18)
C7—H7A	0.9700	N4—H4A	0.87 (2)
C7—H7B	0.9700	N4—H4B	0.86 (2)
C8—O9	1.416 (3)	O8—H8	0.91 (3)
C8—H8A	0.9700

O7—C1—C2	120.48 (13)	O9—C9—C10	111.16 (15)
O7—C1—C6	126.99 (13)	O9—C9—H9A	109.4
C2—C1—C6	112.53 (11)	C10—C9—H9A	109.4
C3—C2—C1	126.43 (12)	O9—C9—H9B	109.4
C3—C2—N2	118.38 (12)	C10—C9—H9B	109.4
C1—C2—N2	115.13 (12)	H9A—C9—H9B	108.0
O8—C3—C2	119.07 (12)	N4—C10—C9	108.79 (14)
O8—C3—C4	124.16 (12)	N4—C10—H10A	109.9
C2—C3—C4	116.77 (12)	C9—C10—H10A	109.9
C5—C4—C3	120.65 (12)	N4—C10—H10B	109.9
C5—C4—N3	118.42 (12)	C9—C10—H10B	109.9
C3—C4—N3	120.92 (12)	H10A—C10—H10B	108.3
C6—C5—C4	120.95 (13)	O1—N1—O2	122.51 (13)
C6—C5—H5	119.1 (13)	O1—N1—C6	119.61 (13)
C4—C5—H5	119.9 (13)	O2—N1—C6	117.88 (12)
C5—C6—C1	122.56 (12)	O3—N2—O4	123.56 (16)
C5—C6—N1	116.61 (13)	O3—N2—C2	118.88 (15)
C1—C6—N1	120.83 (12)	O4—N2—C2	117.55 (15)
N4—C7—C8	109.05 (15)	O6—N3—O5	121.80 (13)
N4—C7—H7A	109.9	O6—N3—C4	119.89 (13)
C8—C7—H7A	109.9	O5—N3—C4	118.30 (13)
N4—C7—H7B	109.9	C10—N4—C7	110.99 (13)
C8—C7—H7B	109.9	C10—N4—H4A	107.0 (14)
H7A—C7—H7B	108.3	C7—N4—H4A	109.7 (14)
O9—C8—C7	111.04 (15)	C10—N4—H4B	110.8 (14)
O9—C8—H8A	109.4	C7—N4—H4B	107.9 (14)
C7—C8—H8A	109.4	H4A—N4—H4B	110.4 (19)
O9—C8—H8B	109.4	C3—O8—H8	103.0 (16)
C7—C8—H8B	109.4	C8—O9—C9	109.86 (13)
H8A—C8—H8B	108.0

O7—C1—C2—C3	177.37 (14)	C2—C1—C6—N1	178.50 (11)
C6—C1—C2—C3	−2.0 (2)	N4—C7—C8—O9	57.88 (19)
O7—C1—C2—N2	0.1 (2)	O9—C9—C10—N4	−58.2 (2)
C6—C1—C2—N2	−179.23 (12)	C5—C6—N1—O1	177.61 (13)
C1—C2—C3—O8	−176.85 (13)	C1—C6—N1—O1	−2.3 (2)
N2—C2—C3—O8	0.29 (19)	C5—C6—N1—O2	−3.30 (19)
C1—C2—C3—C4	3.7 (2)	C1—C6—N1—O2	176.81 (13)
N2—C2—C3—C4	−179.14 (12)	C3—C2—N2—O3	99.3 (2)
O8—C3—C4—C5	178.49 (12)	C1—C2—N2—O3	−83.3 (2)
C2—C3—C4—C5	−2.12 (19)	C3—C2—N2—O4	−80.3 (2)
O8—C3—C4—N3	−0.6 (2)	C1—C2—N2—O4	97.2 (2)
C2—C3—C4—N3	178.84 (12)	C5—C4—N3—O6	10.8 (2)
C3—C4—C5—C6	−1.0 (2)	C3—C4—N3—O6	−170.13 (14)
N3—C4—C5—C6	178.09 (12)	C5—C4—N3—O5	−168.37 (13)
C4—C5—C6—C1	2.8 (2)	C3—C4—N3—O5	10.7 (2)
C4—C5—C6—N1	−177.07 (12)	C9—C10—N4—C7	54.78 (19)
O7—C1—C6—C5	179.29 (14)	C8—C7—N4—C10	−54.73 (19)
C2—C1—C6—C5	−1.38 (19)	C7—C8—O9—C9	−61.7 (2)
O7—C1—C6—N1	−0.8 (2)	C10—C9—O9—C8	62.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O5	0.91 (3)	1.75 (3)	2.571 (2)	149 (2)
N4—H4A···O7	0.87 (2)	1.87 (2)	2.715 (2)	164 (2)
N4—H4B···O2ⁱ	0.86 (2)	2.31 (2)	2.962 (2)	132.4 (17)
N4—H4B···O5ⁱⁱ	0.86 (2)	2.42 (2)	2.967 (2)	121.5 (17)
N4—H4B···O3ⁱⁱⁱ	0.86 (2)	2.54 (2)	3.206 (3)	134.3 (17)

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

Experimental details

Crystal data
Chemical formula	C₄H₁₀NO⁺·C₆H₂N₃O₈⁻
M_r	332.24
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.680 (5), 7.973 (5), 11.852 (5)
α, β, γ (°)	94.785 (5), 99.016 (5), 108.188 (5)
V (Å³)	674.1 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.30 × 0.16 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.957, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	16214, 3841, 2944
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.699

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.157, 1.06
No. of reflections	3841
No. of parameters	225
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.38

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O5	0.91 (3)	1.75 (3)	2.571 (2)	149 (2)
N4—H4A···O7	0.87 (2)	1.87 (2)	2.715 (2)	164 (2)
N4—H4B···O2ⁱ	0.86 (2)	2.31 (2)	2.962 (2)	132.4 (17)
N4—H4B···O5ⁱⁱ	0.86 (2)	2.42 (2)	2.967 (2)	121.5 (17)
N4—H4B···O3ⁱⁱⁱ	0.86 (2)	2.54 (2)	3.206 (3)	134.3 (17)

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

Acknowledgements

The authors are thankful to the SAIF, IIT Madras, for the data collection.

References

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