Gabapentinium picrate

Li, H.; Yathirajan, H.S.; Mallesha, L.; Mohana, K.N.; Narayana, B.

doi:10.1107/S1600536809008952

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o783

doi:10.1107/S1600536809008952

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Gabapentinium picrate

Hongqi Li,^a ^* H. S. Yathirajan,^b L. Mallesha,^b K. N. Mohana ^b and B. Narayana ^c

^aKey Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, People's Republic of China, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: hongqili@dhu.edu.cn

(Received 16 December 2008; accepted 11 March 2009; online 19 March 2009)

The title compound {systematic name: [1-(carboxymethyl)cyclohexyl]methanaminium 2,4,6-trinitrophenolate}, C₉H₁₈NO₂⁺·C₆H₂N₃O₇⁻, was synthesized from picric acid and gabapentin. The crystal packing is stabilized by intramolecular N—H⋯O=N and N—H⋯O—Ph hydrogen bonds. An O—H⋯O interaction is also present.

Related literature

For background, see: Bryans & Wustrow (1999 ). For related structures, see: Ibers (2001 ); Swamy et al. (2007 ) and references cited therein.

Experimental

Crystal data

C₉H₁₈NO₂⁺·C₆H₂N₃O₇⁻
M_r = 400.35
Monoclinic, P 2₁ /n
a = 11.576 (2) Å
b = 7.7312 (16) Å
c = 19.973 (4) Å
β = 91.425 (2)°
V = 1787.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 K
0.25 × 0.25 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.970, T_max = 0.976
8899 measured reflections
3150 independent reflections
2408 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.182
S = 1.07
3150 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 1.06 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9⋯O8ⁱ	0.82	1.86	2.672 (3)	174
N4—H4C⋯O4ⁱⁱ	0.89	2.32	2.957 (4)	128
N4—H4C⋯O3ⁱⁱ	0.89	2.06	2.862 (3)	149
N4—H4B⋯O2ⁱⁱⁱ	0.89	2.41	2.894 (3)	114
N4—H4B⋯O4ⁱ	0.89	2.23	3.063 (3)	155
N4—H4A⋯O3ⁱⁱⁱ	0.89	2.21	3.081 (3)	166
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008952/cs2105sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809008952/cs2105Isup2.hkl

checkCIF report

Comment top

Gabapentin, (1-(aminomethyl) cyclohexane acetic acid; Neurontin), is a novel anticonvulsant agent and has therapeutically beneficial effects against chronic pain states and anxiety (Bryans & Wustrow, 1999). Gabapentin is a zwitterion in the solid state (Ibers, 2001). On the other hand, picric acid forms salts or charge-transfer complexes with many organic compounds and we have reported crystal structures of a number of picrate complexes with organic compounds of pharmaceutical importance viz. desipraminium picrate (Swamy et al., 2007). The present paper reports the crystal structure of the title compound, (1-(carboxymethyl)cyclohexyl)methanaminium 2,4,6-trinitrophenolate.

Related literature top

For background, see: Bryans & Wustrow (1999). For related structures, see: Ibers (2001); Swamy et al. (2007) and references cited therein.

Experimental top

The title compound was synthesized by mixing solutions of picric acid (4.59 g, 0.01 mol) in 20 ml of distilled water and gabapentin (1.72 g, 0.01 mol) in 20 ml of distilled water and the resulting solution was stirred well for 10 min. A yellow precipitate of gabapentinium picrate was formed almost instantaneously after stirring. The so formed yellow complex was filtered off, washed with distilled water and dried in vacuo over anhydrous calcium chloride. The compound was purified by successive recrystallization from methanol (yield 92%). Single crystals for X-ray studies were grown by slow evaporation of a methanol solution. Analysis (%) found (calculated) for C₁₅H₂₀N₄O₉: C: 44.68 (45.00); H: 5.11 (5.04); N: 13.73 (13.99)%.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Packing in the crystal structure of the title compound, viewed along the a axis

[1-(Carboxymethyl)cyclohexyl]methanaminium 2,4,6-trinitrophenolate top

Crystal data top

C₉H₁₈NO₂⁺·C₆H₂N₃O₇⁻	F(000) = 840
M_r = 400.35	D_x = 1.488 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 431–434 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.576 (2) Å	Cell parameters from 2666 reflections
b = 7.7312 (16) Å	θ = 2.8–25.1°
c = 19.973 (4) Å	µ = 0.12 mm⁻¹
β = 91.425 (2)°	T = 296 K
V = 1787.0 (6) Å³	Block, yellow
Z = 4	0.25 × 0.25 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3150 independent reflections
Radiation source: fine-focus sealed tube	2408 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −12→13
T_min = 0.970, T_max = 0.976	k = −7→9
8899 measured reflections	l = −23→23

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)] = 0.062	H-atom parameters constrained
wR(F²) = 0.182	w = 1/[σ²(F_o²) + (0.083P)² + 1.5949P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3150 reflections	Δρ_max = 1.06 e Å⁻³
256 parameters	Δρ_min = −0.55 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.075 (5)

Crystal data top

C₉H₁₈NO₂⁺·C₆H₂N₃O₇⁻	V = 1787.0 (6) Å³
M_r = 400.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.576 (2) Å	µ = 0.12 mm⁻¹
b = 7.7312 (16) Å	T = 296 K
c = 19.973 (4) Å	0.25 × 0.25 × 0.20 mm
β = 91.425 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3150 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2408 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.976	R_int = 0.034
8899 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.182	H-atom parameters constrained
S = 1.07	Δρ_max = 1.06 e Å⁻³
3150 reflections	Δρ_min = −0.55 e Å⁻³
256 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.2919 (2)	0.3970 (4)	0.05392 (13)	0.0375 (6)
C2	0.3067 (2)	0.5162 (3)	0.10930 (13)	0.0362 (6)
C3	0.3639 (2)	0.6728 (3)	0.08832 (16)	0.0432 (7)
C4	0.3949 (2)	0.7066 (4)	0.02348 (17)	0.0499 (8)
H4	0.4323	0.8093	0.0131	0.060*
C5	0.3701 (2)	0.5869 (4)	−0.02563 (15)	0.0466 (8)
C6	0.3199 (2)	0.4315 (4)	−0.01060 (14)	0.0433 (7)
H6	0.3052	0.3503	−0.0441	0.052*
C7	0.4810 (2)	0.6530 (3)	0.67642 (12)	0.0328 (6)
C8	0.5192 (2)	0.4847 (3)	0.71209 (13)	0.0372 (6)
H8A	0.6030	0.4811	0.7144	0.045*
H8B	0.4920	0.4871	0.7576	0.045*
C9	0.4752 (3)	0.3205 (4)	0.67810 (17)	0.0521 (8)
H9A	0.5112	0.3084	0.6350	0.063*
H9B	0.4972	0.2213	0.7053	0.063*
C10	0.3458 (3)	0.3223 (5)	0.6679 (2)	0.0727 (11)
H10A	0.3093	0.3214	0.7111	0.087*
H10B	0.3216	0.2192	0.6437	0.087*
C11	0.3074 (3)	0.4818 (5)	0.6289 (2)	0.0664 (10)
H11A	0.2237	0.4833	0.6247	0.080*
H11B	0.3381	0.4771	0.5842	0.080*
C12	0.3490 (3)	0.6467 (4)	0.66370 (16)	0.0502 (8)
H12A	0.3109	0.6569	0.7062	0.060*
H12B	0.3261	0.7453	0.6364	0.060*
C13	0.5043 (3)	0.8069 (4)	0.72276 (14)	0.0429 (7)
H13A	0.4866	0.9122	0.6982	0.051*
H13B	0.4517	0.8003	0.7597	0.051*
C14	0.5472 (2)	0.6665 (3)	0.61064 (12)	0.0354 (6)
H14A	0.6290	0.6669	0.6222	0.042*
H14B	0.5319	0.5615	0.5853	0.042*
C15	0.5244 (2)	0.8160 (3)	0.56474 (13)	0.0365 (6)
N1	0.2450 (3)	0.2259 (3)	0.06681 (13)	0.0530 (7)
N2	0.3944 (3)	0.8022 (3)	0.13862 (17)	0.0582 (8)
N3	0.4040 (2)	0.6182 (5)	−0.09448 (17)	0.0633 (9)
N4	0.6251 (2)	0.8199 (3)	0.75081 (12)	0.0490 (7)
H4A	0.6443	0.7210	0.7710	0.074*
H4B	0.6292	0.9060	0.7803	0.074*
H4C	0.6734	0.8404	0.7178	0.074*
O1	0.1815 (4)	0.1631 (5)	0.02309 (16)	0.1380 (18)
O2	0.2579 (2)	0.1585 (3)	0.11974 (12)	0.0681 (8)
O3	0.2754 (2)	0.4861 (3)	0.16754 (10)	0.0492 (6)
O4	0.3311 (2)	0.8242 (3)	0.18624 (13)	0.0638 (7)
O5	0.4804 (3)	0.8876 (4)	0.1315 (2)	0.1066 (12)
O6	0.4584 (2)	0.7510 (5)	−0.10551 (16)	0.0911 (10)
O7	0.3773 (3)	0.5105 (5)	−0.13704 (14)	0.0893 (10)
O8	0.4688 (2)	0.9447 (3)	0.57786 (10)	0.0609 (7)
O9	0.5759 (2)	0.7959 (3)	0.50733 (11)	0.0616 (7)
H9	0.5576	0.8754	0.4820	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0436 (15)	0.0344 (14)	0.0344 (14)	−0.0022 (12)	−0.0046 (11)	0.0041 (11)
C2	0.0400 (14)	0.0318 (14)	0.0364 (15)	0.0020 (11)	−0.0054 (11)	0.0019 (11)
C3	0.0420 (15)	0.0297 (14)	0.0575 (18)	−0.0008 (12)	−0.0075 (13)	0.0030 (13)
C4	0.0384 (16)	0.0382 (16)	0.073 (2)	0.0036 (13)	0.0079 (14)	0.0239 (16)
C5	0.0394 (15)	0.0549 (19)	0.0457 (16)	0.0112 (14)	0.0059 (12)	0.0156 (15)
C6	0.0428 (16)	0.0514 (18)	0.0356 (15)	0.0031 (13)	−0.0026 (12)	0.0021 (13)
C7	0.0415 (14)	0.0297 (13)	0.0271 (13)	0.0035 (11)	0.0006 (10)	0.0015 (10)
C8	0.0490 (16)	0.0323 (14)	0.0301 (14)	−0.0001 (12)	−0.0014 (11)	0.0044 (11)
C9	0.073 (2)	0.0313 (16)	0.0520 (18)	−0.0097 (15)	−0.0040 (15)	0.0041 (13)
C10	0.076 (3)	0.058 (2)	0.084 (3)	−0.031 (2)	0.002 (2)	0.004 (2)
C11	0.0460 (19)	0.078 (3)	0.074 (2)	−0.0127 (18)	−0.0084 (16)	−0.001 (2)
C12	0.0416 (16)	0.059 (2)	0.0505 (18)	0.0065 (14)	0.0054 (13)	0.0072 (15)
C13	0.0624 (19)	0.0337 (15)	0.0325 (14)	0.0073 (13)	0.0012 (13)	−0.0009 (11)
C14	0.0466 (15)	0.0311 (14)	0.0285 (13)	0.0016 (11)	0.0016 (11)	0.0015 (10)
C15	0.0480 (16)	0.0346 (15)	0.0268 (13)	−0.0010 (12)	−0.0009 (11)	0.0005 (11)
N1	0.0781 (19)	0.0435 (15)	0.0369 (14)	−0.0202 (13)	−0.0054 (12)	−0.0054 (12)
N2	0.0603 (17)	0.0320 (14)	0.082 (2)	−0.0054 (13)	−0.0139 (16)	−0.0025 (14)
N3	0.0510 (16)	0.078 (2)	0.0612 (19)	0.0195 (16)	0.0141 (14)	0.0320 (18)
N4	0.0808 (19)	0.0321 (13)	0.0337 (13)	−0.0104 (12)	−0.0085 (12)	−0.0038 (10)
O1	0.240 (5)	0.111 (3)	0.0613 (19)	−0.105 (3)	−0.031 (2)	0.0042 (18)
O2	0.0992 (19)	0.0492 (14)	0.0547 (15)	−0.0240 (13)	−0.0203 (13)	0.0170 (11)
O3	0.0769 (15)	0.0367 (11)	0.0340 (11)	−0.0009 (10)	0.0009 (10)	0.0000 (8)
O4	0.0849 (18)	0.0401 (13)	0.0655 (16)	0.0009 (12)	−0.0174 (14)	−0.0124 (11)
O5	0.089 (2)	0.072 (2)	0.159 (3)	−0.0438 (18)	0.005 (2)	−0.029 (2)
O6	0.0774 (19)	0.101 (2)	0.096 (2)	0.0071 (17)	0.0278 (16)	0.0562 (19)
O7	0.106 (2)	0.116 (3)	0.0471 (15)	0.016 (2)	0.0227 (15)	0.0115 (17)
O8	0.1037 (19)	0.0422 (13)	0.0375 (12)	0.0242 (13)	0.0137 (11)	0.0090 (10)
O9	0.0925 (18)	0.0544 (14)	0.0389 (12)	0.0224 (13)	0.0198 (11)	0.0148 (10)

Geometric parameters (Å, º) top

C1—C6	1.363 (4)	C10—H10B	0.9700
C1—C2	1.447 (4)	C11—C12	1.524 (5)
C1—N1	1.455 (4)	C11—H11A	0.9700
C2—O3	1.249 (3)	C11—H11B	0.9700
C2—C3	1.447 (4)	C12—H12A	0.9700
C3—C4	1.377 (4)	C12—H12B	0.9700
C3—N2	1.455 (4)	C13—N4	1.497 (4)
C4—C5	1.374 (5)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—C6	1.371 (4)	C14—C15	1.495 (4)
C5—N3	1.460 (4)	C14—H14A	0.9700
C6—H6	0.9300	C14—H14B	0.9700
C7—C13	1.527 (4)	C15—O8	1.217 (3)
C7—C14	1.541 (3)	C15—O9	1.314 (3)
C7—C8	1.543 (3)	N1—O2	1.185 (3)
C7—C12	1.544 (4)	N1—O1	1.228 (4)
C8—C9	1.522 (4)	N2—O5	1.205 (4)
C8—H8A	0.9700	N2—O4	1.227 (4)
C8—H8B	0.9700	N3—O7	1.225 (4)
C9—C10	1.506 (5)	N3—O6	1.227 (4)
C9—H9A	0.9700	N4—H4A	0.8900
C9—H9B	0.9700	N4—H4B	0.8900
C10—C11	1.520 (5)	N4—H4C	0.8900
C10—H10A	0.9700	O9—H9	0.8200

C6—C1—C2	124.9 (3)	C10—C11—H11A	109.4
C6—C1—N1	116.3 (3)	C12—C11—H11A	109.4
C2—C1—N1	118.8 (2)	C10—C11—H11B	109.4
O3—C2—C1	124.2 (2)	C12—C11—H11B	109.4
O3—C2—C3	124.8 (3)	H11A—C11—H11B	108.0
C1—C2—C3	111.0 (2)	C11—C12—C7	113.7 (3)
C4—C3—C2	124.2 (3)	C11—C12—H12A	108.8
C4—C3—N2	117.0 (3)	C7—C12—H12A	108.8
C2—C3—N2	118.7 (3)	C11—C12—H12B	108.8
C5—C4—C3	119.3 (3)	C7—C12—H12B	108.8
C5—C4—H4	120.4	H12A—C12—H12B	107.7
C3—C4—H4	120.4	N4—C13—C7	115.4 (2)
C6—C5—C4	121.1 (3)	N4—C13—H13A	108.4
C6—C5—N3	118.5 (3)	C7—C13—H13A	108.4
C4—C5—N3	120.3 (3)	N4—C13—H13B	108.4
C1—C6—C5	119.4 (3)	C7—C13—H13B	108.4
C1—C6—H6	120.3	H13A—C13—H13B	107.5
C5—C6—H6	120.3	C15—C14—C7	119.4 (2)
C13—C7—C14	112.4 (2)	C15—C14—H14A	107.5
C13—C7—C8	109.4 (2)	C7—C14—H14A	107.5
C14—C7—C8	107.9 (2)	C15—C14—H14B	107.5
C13—C7—C12	106.5 (2)	C7—C14—H14B	107.5
C14—C7—C12	111.9 (2)	H14A—C14—H14B	107.0
C8—C7—C12	108.7 (2)	O8—C15—O9	122.6 (2)
C9—C8—C7	114.1 (2)	O8—C15—C14	125.9 (2)
C9—C8—H8A	108.7	O9—C15—C14	111.5 (2)
C7—C8—H8A	108.7	O2—N1—O1	121.3 (3)
C9—C8—H8B	108.7	O2—N1—C1	121.2 (2)
C7—C8—H8B	108.7	O1—N1—C1	117.0 (3)
H8A—C8—H8B	107.6	O5—N2—O4	121.8 (3)
C10—C9—C8	111.9 (3)	O5—N2—C3	118.9 (3)
C10—C9—H9A	109.2	O4—N2—C3	119.4 (3)
C8—C9—H9A	109.2	O7—N3—O6	124.5 (3)
C10—C9—H9B	109.2	O7—N3—C5	118.1 (3)
C8—C9—H9B	109.2	O6—N3—C5	117.3 (4)
H9A—C9—H9B	107.9	C13—N4—H4A	109.5
C9—C10—C11	110.7 (3)	C13—N4—H4B	109.5
C9—C10—H10A	109.5	H4A—N4—H4B	109.5
C11—C10—H10A	109.5	C13—N4—H4C	109.5
C9—C10—H10B	109.5	H4A—N4—H4C	109.5
C11—C10—H10B	109.5	H4B—N4—H4C	109.5
H10A—C10—H10B	108.1	C15—O9—H9	109.5
C10—C11—C12	111.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9···O8ⁱ	0.82	1.86	2.672 (3)	174
N4—H4C···O4ⁱⁱ	0.89	2.32	2.957 (4)	128
N4—H4C···O3ⁱⁱ	0.89	2.06	2.862 (3)	149
N4—H4B···O2ⁱⁱⁱ	0.89	2.41	2.894 (3)	114
N4—H4B···O4ⁱ	0.89	2.23	3.063 (3)	155
N4—H4A···O3ⁱⁱⁱ	0.89	2.21	3.081 (3)	166

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

Experimental details

Crystal data
Chemical formula	C₉H₁₈NO₂⁺·C₆H₂N₃O₇⁻
M_r	400.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	11.576 (2), 7.7312 (16), 19.973 (4)
β (°)	91.425 (2)
V (Å³)	1787.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.25 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.970, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	8899, 3150, 2408
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.182, 1.07
No. of reflections	3150
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.06, −0.55

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9···O8ⁱ	0.82	1.86	2.672 (3)	174.4
N4—H4C···O4ⁱⁱ	0.89	2.32	2.957 (4)	128.0
N4—H4C···O3ⁱⁱ	0.89	2.06	2.862 (3)	148.6
N4—H4B···O2ⁱⁱⁱ	0.89	2.41	2.894 (3)	114.4
N4—H4B···O4ⁱ	0.89	2.23	3.063 (3)	154.7
N4—H4A···O3ⁱⁱⁱ	0.89	2.21	3.081 (3)	166.4

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

Acknowledgements

LM thanks University of Mysore for research facilities.

References

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