4-(2-Chloro­ethyl)morpholinium picrate

Kant, R.; Kohli, S.; Sarmal, L.; Narayana, B.; Samshuddin, S.

doi:10.1107/S1600536809035405

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2435

doi:10.1107/S1600536809035405

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4-(2-Chloroethyl)morpholinium picrate

Rajni Kant,^a ^* Sabeta Kohli,^a Lovely Sarmal,^a B. Narayana ^b and S. Samshuddin ^b

^aDepartment of Physics, University of Jammu, Jammu Tawi 180 006, India, and ^bDepartment of Studies in Chemistry, Mangalore University, Magalagangotri 574 199, India
^*Correspondence e-mail: rk_paper@rediffmail.com

(Received 22 July 2009; accepted 2 September 2009; online 12 September 2009)

The title compound, C₆H₁₃ClNO⁺·C₆H₂N₃O₇⁻, was synthesized from picric acid and 4-(2-chloroethyl)morpholine. The crystal structure is stabilized by C—H⋯O and N—H⋯O hydrogen-bond interactions.

Related literature

For the homeopathic uses of the metal derivatives of picric acid, see: Maurya et al. (1999 ). For the medical applications of ammonium picrate, see: Boericke (1982 ) and of morpholine derivatives, see: Lutz et al. (1947 ); Hazard et al. (1948 ); Raymond et al. (1999 ). For a related structure, see: Briggs et al. (2004 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₆H₁₃ClNO⁺·C₆H₂N₃O₇⁻
M_r = 378.72
Triclinic, $[P \overline 1]$
a = 8.2063 (4) Å
b = 9.3075 (5) Å
c = 10.2896 (6) Å
α = 93.954 (5)°
β = 95.284 (5)°
γ = 90.376 (4)°
V = 780.65 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 293 K
0.30 × 0.24 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: none
8478 measured reflections
4960 independent reflections
3665 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.179
S = 1.12
4960 reflections
286 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4′⋯O1	0.91 (3)	1.89 (3)	2.718 (2)	151.2 (19)
N4—H4′⋯O2	0.91 (3)	2.25 (2)	2.896 (2)	127.6 (17)
C2—H2⋯O3	0.83 (3)	2.34 (3)	2.637 (3)	102 (2)
C2—H2⋯O4	0.83 (2)	2.45 (2)	2.723 (3)	101 (2)
C4—H4⋯O6	0.90 (3)	2.34 (3)	2.667 (3)	101.7 (15)
C7—H7A⋯O7ⁱ	0.93 (3)	2.54 (3)	3.026 (3)	113 (2)
C8—H8B⋯O5ⁱⁱ	0.94 (3)	2.47 (2)	3.290 (2)	146 (2)
C9—H9A⋯O5ⁱⁱ	0.97 (3)	2.45 (3)	3.341 (2)	154 (2)
C9—H9B⋯O2	0.97 (3)	2.34 (3)	2.985 (3)	123 (2)
C12—H12A⋯O1	0.96 (3)	2.57 (2)	3.254 (3)	129 (2)
Symmetry codes: (i) -x, -y, -z+1; (ii) x-1, y-1, z.

Data collection: CrysAlis Pro (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis Pro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis Pro; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis Pro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows(Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035405/jh2096sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035405/jh2096Isup2.hkl

checkCIF report

Comment top

The metal derivatives of picric acid are also known as medicines in homeopathy (Maurya et al., 1999). Silver picrate is a good antimicrobial agent. Zinc picrate is used in Bright's disease, headache, exhaustion, facial paralysis, nymphomania, paralysis, seminal emissions, spiral weakness, loss of memory and energy.

Ammonium picrate is a remedy for malarial fever and neuralgia, whooping cough, pain in the occiput and mastoid regions (Boericke, 1982).

N-substituted morpholines were used as anti-malarials (Lutz et al., 1947) and 4-methyl-4-(2-phenylethyl)-morpholinium iodide have shown marked hypertension in dogs at a dose of 5 mg./kg (Hazard et al., 1948). Morpholine derivatives are also used as agricultural fungicides in cereals and are known as ergosterol biosynthesis inhibitors (Raymond et al., 1999).

A search of the Cambridge Structural Database (Version 5.26; Allen, 2002) reveals that there are 90 known structures that contain the morpholinium cation. Of these there are 24 that have an N-ethyl chain, or longer, including the structure of 4-(2-fluoroethyl) morpholinium chloride (Briggs et al., 2004).

The title compound, [C₆H₁₃Cl N O]⁺[C₆ H₂N₃ O₇]^-, was synthesized from picric acid and 4-(2-chloroethyl)morpholine.All geometrical parameters are in their usual ranges. The crystal structure is stabilized by C—H···O and N—H···O hydrogen interactions.

Related literature top

For the homeopathic uses of the metal derivatives of picric acid, see: Maurya et al. (1999). For the medical applications of ammonium picrate, see: Boericke (1982) and of morpholine derivatives, see: Lutz et al. (1947); Hazard et al. (1948); Raymond et al. (1999).For a related structure, see: Briggs et al. (2004). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

Picric acid (2.29 g, 0.01 mol) was dissolved in water. 4-(2-chloroethyl) morpholine (1.49 g 0.01 mol) was dissolved in 25 ml of ethanol. The two solutions were mixed and 5 ml of 5 M HCl was added to this mixture and stirred for few minutes,filtered, dried and yellow crystals of 4-(2-Chloroethyl)morpholinium picrate were obtained by slow evaporation in ethanol. (m.p. 394 K). Analytical data: Found (Cald): C %: 36.89(37.96); H%: 4.22 (4.25); N%:14.67(14.75).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows(Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of (I) (50% probability displacement ellipsoids).
	Fig. 2. Depiction of C—H···O and N—H···O interactions in the title compound(I)

4-(2-Chloroethyl)morpholinium picrate top

Crystal data top

C₆H₁₃ClNO⁺·C₆H₂N₃O₇⁻	Z = 2
M_r = 378.72	F(000) = 392
Triclinic, P1	D_x = 1.611 Mg m⁻³
a = 8.2063 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3075 (5) Å	Cell parameters from 3665 reflections
c = 10.2896 (6) Å	θ = 3.3–32.3°
α = 93.954 (5)°	µ = 0.30 mm⁻¹
β = 95.284 (5)°	T = 293 K
γ = 90.376 (4)°	Rectangular, yellow
V = 780.65 (7) Å³	0.30 × 0.24 × 0.18 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	R_int = 0.016
ω–2θ scans	θ_max = 32.3°, θ_min = 3.3°
8478 measured reflections	h = −12→12
4960 independent reflections	k = −8→13
3665 reflections with I > 2σ(I)	l = −14→15

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	0 constraints
R[F² > 2σ(F²)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.179	w = 1/[σ²(F_o²) + (0.0877P)² + 0.2886P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
4960 reflections	Δρ_max = 0.85 e Å⁻³
286 parameters	Δρ_min = −0.61 e Å⁻³

Crystal data top

C₆H₁₃ClNO⁺·C₆H₂N₃O₇⁻	γ = 90.376 (4)°
M_r = 378.72	V = 780.65 (7) Å³
Triclinic, P1	Z = 2
a = 8.2063 (4) Å	Mo Kα radiation
b = 9.3075 (5) Å	µ = 0.30 mm⁻¹
c = 10.2896 (6) Å	T = 293 K
α = 93.954 (5)°	0.30 × 0.24 × 0.18 mm
β = 95.284 (5)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	3665 reflections with I > 2σ(I)
8478 measured reflections	R_int = 0.016
4960 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.179	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.85 e Å⁻³
4960 reflections	Δρ_min = −0.61 e Å⁻³
286 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
H8B	−0.178 (3)	−0.150 (3)	0.786 (2)	0.035 (6)*
H9B	−0.286 (3)	0.146 (3)	0.883 (3)	0.041 (6)*
H4	0.386 (3)	0.587 (2)	0.610 (2)	0.033 (6)*
H9A	−0.401 (3)	0.024 (3)	0.793 (2)	0.036 (6)*
H10A	−0.331 (3)	0.311 (3)	0.731 (2)	0.039 (6)*
H2	0.299 (3)	0.541 (3)	0.972 (3)	0.042 (7)*
H11A	−0.135 (3)	−0.023 (3)	0.548 (2)	0.040 (6)*
H12A	−0.241 (3)	0.215 (3)	0.532 (3)	0.049 (7)*
H8A	−0.102 (3)	−0.044 (2)	0.887 (3)	0.033 (6)*
H11B	−0.300 (3)	−0.076 (3)	0.597 (2)	0.037 (6)*
H7B	0.087 (4)	−0.208 (3)	0.791 (3)	0.058 (8)*
H12B	−0.355 (4)	0.101 (3)	0.435 (3)	0.055 (8)*
H7A	0.069 (3)	−0.121 (3)	0.678 (3)	0.052 (7)*
H10B	−0.504 (4)	0.259 (3)	0.757 (3)	0.052 (7)*
H4'	−0.106 (3)	0.125 (3)	0.743 (2)	0.037 (6)*
Cl	0.22010 (6)	0.00390 (7)	0.83918 (7)	0.0572 (2)
N4	−0.18045 (17)	0.05189 (15)	0.73274 (15)	0.0277 (3)
C8	−0.1068 (2)	−0.0703 (2)	0.8042 (2)	0.0333 (4)
C9	−0.3282 (2)	0.1067 (2)	0.7962 (2)	0.0343 (4)
O8	−0.4535 (2)	0.1794 (2)	0.58892 (18)	0.0535 (4)
C11	−0.2318 (2)	0.0085 (2)	0.5915 (2)	0.0365 (4)
C10	−0.4054 (3)	0.2269 (2)	0.7217 (3)	0.0469 (5)
C7	0.0592 (2)	−0.1150 (2)	0.7678 (2)	0.0405 (4)
C12	−0.3138 (3)	0.1338 (3)	0.5261 (2)	0.0465 (5)
C5	0.2198 (2)	0.43814 (18)	0.62764 (19)	0.0308 (3)
N2	0.47503 (19)	0.70058 (17)	0.84556 (19)	0.0374 (4)
C2	0.2800 (2)	0.51646 (19)	0.8933 (2)	0.0325 (4)
O1	0.0317 (2)	0.25764 (19)	0.67334 (16)	0.0543 (5)
C4	0.3325 (2)	0.54510 (18)	0.6696 (2)	0.0318 (4)
C3	0.3613 (2)	0.58362 (18)	0.80201 (19)	0.0310 (4)
C1	0.1667 (2)	0.40844 (18)	0.85050 (19)	0.0311 (4)
C6	0.1275 (2)	0.35914 (19)	0.71437 (19)	0.0330 (4)
N3	0.0845 (2)	0.34768 (17)	0.95407 (18)	0.0384 (4)
N1	0.1924 (2)	0.40692 (18)	0.48624 (17)	0.0389 (4)
O5	0.5335 (2)	0.76658 (17)	0.76105 (19)	0.0541 (4)
O2	−0.0347 (2)	0.2682 (2)	0.92512 (19)	0.0603 (5)
O4	0.5057 (2)	0.73018 (19)	0.96342 (19)	0.0542 (4)
O3	0.1342 (2)	0.3801 (2)	1.06775 (18)	0.0568 (5)
O7	0.0693 (3)	0.3444 (3)	0.4397 (2)	0.0808 (7)
O6	0.2896 (3)	0.4530 (3)	0.4174 (2)	0.0902 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0304 (2)	0.0661 (4)	0.0743 (5)	−0.0029 (2)	0.0023 (2)	0.0011 (3)
N4	0.0240 (6)	0.0286 (6)	0.0314 (7)	−0.0047 (5)	0.0033 (5)	0.0069 (5)
C8	0.0287 (8)	0.0346 (9)	0.0378 (10)	−0.0009 (7)	0.0032 (7)	0.0116 (7)
C9	0.0269 (8)	0.0356 (9)	0.0411 (10)	−0.0010 (6)	0.0065 (7)	0.0041 (7)
O8	0.0401 (8)	0.0624 (10)	0.0567 (11)	0.0076 (7)	−0.0100 (7)	0.0140 (8)
C11	0.0333 (9)	0.0426 (10)	0.0330 (9)	−0.0036 (7)	0.0009 (7)	0.0027 (7)
C10	0.0431 (11)	0.0402 (10)	0.0573 (14)	0.0088 (9)	0.0011 (10)	0.0067 (9)
C7	0.0340 (9)	0.0425 (10)	0.0449 (12)	0.0056 (8)	0.0033 (8)	0.0012 (9)
C12	0.0446 (11)	0.0585 (13)	0.0362 (11)	−0.0044 (10)	−0.0058 (9)	0.0152 (9)
C5	0.0287 (7)	0.0271 (7)	0.0367 (9)	−0.0030 (6)	0.0012 (6)	0.0057 (6)
N2	0.0289 (7)	0.0288 (7)	0.0537 (11)	−0.0048 (6)	0.0011 (7)	0.0009 (7)
C2	0.0306 (8)	0.0285 (8)	0.0382 (10)	−0.0009 (6)	0.0009 (7)	0.0042 (7)
O1	0.0577 (10)	0.0596 (10)	0.0445 (9)	−0.0371 (8)	−0.0041 (7)	0.0103 (7)
C4	0.0265 (7)	0.0258 (7)	0.0442 (10)	−0.0024 (6)	0.0056 (7)	0.0089 (7)
C3	0.0261 (7)	0.0242 (7)	0.0425 (10)	−0.0044 (6)	0.0011 (7)	0.0036 (7)
C1	0.0293 (8)	0.0284 (7)	0.0366 (9)	−0.0038 (6)	0.0041 (7)	0.0083 (7)
C6	0.0282 (8)	0.0305 (8)	0.0409 (10)	−0.0069 (6)	0.0002 (7)	0.0103 (7)
N3	0.0397 (8)	0.0313 (7)	0.0467 (10)	−0.0014 (6)	0.0122 (7)	0.0101 (7)
N1	0.0435 (9)	0.0361 (8)	0.0369 (9)	−0.0018 (7)	0.0037 (7)	0.0020 (7)
O5	0.0504 (9)	0.0417 (8)	0.0711 (12)	−0.0223 (7)	0.0093 (8)	0.0074 (8)
O2	0.0626 (11)	0.0575 (10)	0.0627 (11)	−0.0316 (8)	0.0238 (9)	−0.0016 (8)
O4	0.0494 (9)	0.0505 (9)	0.0590 (11)	−0.0126 (7)	−0.0051 (8)	−0.0080 (8)
O3	0.0639 (11)	0.0647 (11)	0.0439 (9)	−0.0126 (9)	0.0067 (8)	0.0163 (8)
O7	0.0923 (16)	0.1001 (17)	0.0461 (11)	−0.0532 (14)	−0.0013 (10)	−0.0075 (10)
O6	0.0833 (15)	0.142 (2)	0.0462 (11)	−0.0453 (16)	0.0161 (10)	0.0066 (13)

Geometric parameters (Å, º) top

Cl—C7	1.788 (2)	C12—H12A	0.96 (3)
N4—C8	1.497 (2)	C12—H12B	0.99 (3)
N4—C11	1.503 (2)	C5—C4	1.374 (2)
N4—C9	1.504 (2)	C5—C6	1.455 (2)
N4—H4'	0.91 (2)	C5—N1	1.460 (3)
C8—C7	1.500 (3)	N2—O4	1.228 (3)
C8—H8B	0.94 (2)	N2—O5	1.229 (2)
C8—H8A	0.87 (3)	N2—C3	1.449 (2)
C9—C10	1.510 (3)	C2—C3	1.382 (3)
C9—H9B	0.98 (3)	C2—C1	1.386 (2)
C9—H9A	0.97 (2)	C2—H2	0.83 (3)
O8—C12	1.420 (3)	O1—C6	1.250 (2)
O8—C10	1.426 (3)	C4—C3	1.383 (3)
C11—C12	1.517 (3)	C4—H4	0.89 (2)
C11—H11A	0.98 (3)	C1—C6	1.450 (3)
C11—H11B	0.97 (2)	C1—N3	1.456 (2)
C10—H10A	0.98 (3)	N3—O3	1.220 (2)
C10—H10B	0.96 (3)	N3—O2	1.225 (2)
C7—H7B	0.93 (3)	N1—O7	1.206 (3)
C7—H7A	0.94 (3)	N1—O6	1.210 (3)

C8—N4—C11	112.20 (15)	Cl—C7—H7A	105.7 (17)
C8—N4—C9	110.07 (14)	H7B—C7—H7A	103 (3)
C11—N4—C9	108.38 (14)	O8—C12—C11	111.16 (18)
C8—N4—H4'	106.9 (15)	O8—C12—H12A	106.5 (17)
C11—N4—H4'	113.0 (15)	C11—C12—H12A	110.6 (16)
C9—N4—H4'	106.1 (15)	O8—C12—H12B	106.1 (17)
N4—C8—C7	115.12 (16)	C11—C12—H12B	108.8 (16)
N4—C8—H8B	107.4 (14)	H12A—C12—H12B	113 (2)
C7—C8—H8B	108.0 (14)	C4—C5—C6	124.17 (18)
N4—C8—H8A	106.8 (16)	C4—C5—N1	116.02 (16)
C7—C8—H8A	110.2 (15)	C6—C5—N1	119.80 (15)
H8B—C8—H8A	109 (2)	O4—N2—O5	123.60 (17)
N4—C9—C10	110.06 (17)	O4—N2—C3	118.95 (17)
N4—C9—H9B	105.2 (15)	O5—N2—C3	117.44 (18)
C10—C9—H9B	108.9 (15)	C3—C2—C1	118.96 (18)
N4—C9—H9A	105.1 (14)	C3—C2—H2	120.0 (18)
C10—C9—H9A	111.6 (14)	C1—C2—H2	121.0 (18)
H9B—C9—H9A	116 (2)	C5—C4—C3	119.30 (16)
C12—O8—C10	109.70 (17)	C5—C4—H4	118.7 (15)
N4—C11—C12	109.86 (17)	C3—C4—H4	122.0 (15)
N4—C11—H11A	109.0 (14)	C2—C3—C4	121.53 (16)
C12—C11—H11A	111.4 (14)	C2—C3—N2	119.26 (17)
N4—C11—H11B	102.7 (14)	C4—C3—N2	119.18 (16)
C12—C11—H11B	116.2 (14)	C2—C1—C6	124.15 (16)
H11A—C11—H11B	107 (2)	C2—C1—N3	114.57 (17)
O8—C10—C9	111.16 (18)	C6—C1—N3	121.27 (15)
O8—C10—H10A	113.2 (15)	O1—C6—C1	125.59 (17)
C9—C10—H10A	109.7 (14)	O1—C6—C5	122.46 (18)
O8—C10—H10B	105.5 (17)	C1—C6—C5	111.90 (15)
C9—C10—H10B	111.4 (17)	O3—N3—O2	121.69 (18)
H10A—C10—H10B	106 (2)	O3—N3—C1	118.95 (17)
C8—C7—Cl	113.24 (15)	O2—N3—C1	119.35 (18)
C8—C7—H7B	113.2 (19)	O7—N1—O6	121.2 (2)
Cl—C7—H7B	107.2 (18)	O7—N1—C5	119.83 (18)
C8—C7—H7A	114.0 (18)	O6—N1—C5	118.78 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4′···O1	0.91 (3)	1.89 (3)	2.718 (2)	151.2 (19)
N4—H4′···O2	0.91 (3)	2.25 (2)	2.896 (2)	127.6 (17)
C2—H2···O3	0.83 (3)	2.34 (3)	2.637 (3)	102 (2)
C2—H2···O4	0.83 (2)	2.45 (2)	2.723 (3)	101 (2)
C4—H4···O6	0.90 (3)	2.34 (3)	2.667 (3)	101.7 (15)
C7—H7A···O7ⁱ	0.93 (3)	2.54 (3)	3.026 (3)	113 (2)
C8—H8B···O5ⁱⁱ	0.94 (3)	2.47 (2)	3.290 (2)	146 (2)
C9—H9A···O5ⁱⁱ	0.97 (3)	2.45 (3)	3.341 (2)	154 (2)
C9—H9B···O2	0.97 (3)	2.34 (3)	2.985 (3)	123 (2)
C12—H12A···O1	0.96 (3)	2.57 (2)	3.254 (3)	129 (2)

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

Experimental details

Crystal data
Chemical formula	C₆H₁₃ClNO⁺·C₆H₂N₃O₇⁻
M_r	378.72
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.2063 (4), 9.3075 (5), 10.2896 (6)
α, β, γ (°)	93.954 (5), 95.284 (5), 90.376 (4)
V (Å³)	780.65 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.30 × 0.24 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8478, 4960, 3665
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.752

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.179, 1.12
No. of reflections	4960
No. of parameters	286
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.61

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows(Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4'···O1	0.91 (3)	1.89 (3)	2.718 (2)	151.2 (19)
N4—H4'···O2	0.91 (3)	2.25 (2)	2.896 (2)	127.6 (17)
C2—H2···O3	0.83 (3)	2.34 (3)	2.637 (3)	102 (2)
C2—H2···O4	0.83 (2)	2.45 (2)	2.723 (3)	101 (2)
C4—H4···O6	0.90 (3)	2.34 (3)	2.667 (3)	101.7 (15)
C7—H7A···O7ⁱ	0.93 (3)	2.54 (3)	3.026 (3)	113 (2)
C8—H8B···O5ⁱⁱ	0.94 (3)	2.47 (2)	3.290 (2)	146 (2)
C9—H9A···O5ⁱⁱ	0.97 (3)	2.45 (3)	3.341 (2)	154 (2)
C9—H9B···O2	0.97 (3)	2.34 (3)	2.985 (3)	123 (2)
C12—H12A···O1	0.96 (3)	2.57 (2)	3.254 (3)	129 (2)

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

Acknowledgements

The authors are grateful to the Department of Science and Technology of the Government of India for funding under SR/S2/CMP-47/2003 research project.

References

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