2-Amino-1-methyl-4-oxo-4,5-di­hydro-1H-imidazol-3-ium 3-carb­oxy-4-hy­droxy­benzene­sulfonate monohydrate

Malarkodi, A.; Kalaiyarasi, S.; Wilson, K.S.J.; Kumar, R.M.; Chakkaravarthi, G.

doi:10.1107/S2414314617015954

organic compounds

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ISSN: 2414-3146

Volume 2| Part 11| November 2017| x171595

https://doi.org/10.1107/S2414314617015954

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2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium 3-carboxy-4-hydroxybenzenesulfonate monohydrate

A. Malarkodi,^a S. Kalaiyarasi,^b K. S. Joseph Wilson,^a R. Mohan Kumar ^b ^* and G. Chakkaravarthi ^c ^*

^aDepartment of Physics, Arul Anandar College, Madurai 625 514, India, ^bDepartment of Physics, Presidency College, Chennai 600 005, India, and ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: mohan66@hotmail.com, chakkaravarthi_2005@yahoo.com

Edited by A. J. Lough, University of Toronto, Canada (Received 23 October 2017; accepted 2 November 2017; online 17 November 2017)

The asymmetric unit of the title molecular salt, C₄H₇N₃O⁺·C₇H₅O₆S⁻·H₂O, contains a 5-sulfosalicylate anion, a creatininium cation and a water molecule of crystallization. The cation is protonated at the imidazole N atom and the anion is deprotonated at the sulfonic acid group. The creatininium is disordered over two sets of sites with refined site occupancies of 0.771 (3) and 0.229 (3). The benzene ring is approximately orthogonal to the disordered five-membered rings [dihedral angles of 89.7 (2) and 88.3 (8)° for the major and minor occupancy components, respectively]. In the crystal, the ions are connected through pairs of N—H⋯O hydrogen bonds, generating an R₂²(8) ring-motif. An intraionic O—H⋯O hydrogen bond generates an S(6) graph-set motif. Weak C—H⋯O contacts link the ions and water molecule into a two-dimensional network parallel to (001). The structure was refined as a two-component twin.

Keywords: molecular salt; crystal structure; hydrogen bonding.

CCDC reference: 1583586

Structure description

Creatine is extracted from several kinds of muscle and it is endogenously synthesized by the liver and pancreas in humans (Greenhaff et al., 1993 ; Walker, 1979 ). We report herein the synthesis and the crystal structure of the title molecular salt (Fig. 1). Its geometric parameters agree well with those of reported similar structures (Thayanithi et al., 2016 ; Jahubar Ali et al., 2011 ).

Figure 1
The molecular structure of the title molecular salt, with atom labelling and 30% probability displacement ellipsoids. The minor component in the cation is shown with dashed bonds. The intramolecular hydrogen bond in the anion is shown with a dashed line.

The title compound contains a disordered creatininium cation,, with site occupancies of 0.771 (3) for the major component (C2A/N1A/C5A/N4A/C3A/O6A) and 0.229 (3) for minor component (C2B/N1B/C5B/N4B/C3B/O6B), a 5-sulfosalicylate anion and a water molecule in the asymmetric unit. The cation is protonated at the imidizole N atom and the anion is deprotonated at the sulfonic acid group. The benzene ring (C1–C6) is orthogonal to the major [dihedral angle of 89.7 (2)°] and minor [dihedral angle of 88.3 (8)°] components of the five-membered rings. In the asymmetric unit, an intraionic O—H⋯O hydrogen bond generates an S(6) graph-set motif (Fig. 2).

Figure 2
The partial packing of the title molecular salt, showing ring-set motifs. Hydrogen bonds are shown as dashed lines.

In the crystal, an N—H⋯O hydrogen bond (Table 1) links the anions and cations, generating an R₂²(8) ring-motif (Fig. 2). The water molecule links adjacent anions through O—H⋯O hydrogen bonds (Table 1 and Fig. 3). Weak C—H⋯O contacts (Fig. 3 and Table 1) link the components into a two-dimensional network parallel to (001).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯O3	0.82 (1)	2.13 (3)	2.799 (4)	139 (4)
O6—H6A⋯O7	0.82	1.90	2.624 (3)	146
N1A—H1A⋯O3ⁱ	0.86	2.00	2.844 (5)	168
O2—H2A⋯O5ⁱⁱ	0.82 (1)	1.99 (2)	2.780 (4)	161 (5)
N8A—H8AA⋯O6Aⁱⁱ	0.86	2.07	2.917 (5)	168
N8A—H8AB⋯O5ⁱ	0.86	1.94	2.788 (4)	170
O8—H8⋯O2ⁱⁱⁱ	0.82	1.85	2.616 (3)	155
C6A—H6AB⋯O4^iv	0.96	2.44	3.194 (7)	135
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) x+1, y, z; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Figure 3
The crystal packing of the title molecular salt viewed along the a axis. The hydrogen bonds are shown as dashed lines. H atoms not involving in hydrogen bonds have been omitted for clarity.

Synthesis and crystallization

The title compound was synthesized from the raw materials creatinine and 5-sulfosalicylic acid which were taken in a stoichiometric ratio and dissolved in water at ambient temperature. The solution was stirred for continuously six h to obtain a transparent homogeneous solution. The solution was filtered using Whatmann filter paper and the beaker containing the solution was covered with a perforated polythene cover. The saturated homogeneous solution was allowed to evaporate, yielding good quality crystals suitable for X-ray diffraction after three weeks.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The structure was refined as two-component twin with twin law $[\overline{1}]$ 0 0 0 $[\overline{1}]$ 0 0 0 1. The creatinium cation is disordered over two orientations with site occupancies of 0.771 (3) and 0.229 (3). The EADP restraint in SHELXL (Sheldrick, 2015 ) was applied for the disordered atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₄H₇N₃O⁺·C₇H₅O₆S⁻·H₂O
M_r	348.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.2459 (2), 15.5638 (4), 13.0774 (3)
β (°)	90.100 (1)
V (Å³)	1474.79 (7)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	2.42
Crystal size (mm)	0.15 × 0.15 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.587, 0.754
No. of measured, independent and observed [I > 2σ(I)] reflections	22225, 2905, 2798
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.620

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.129, 1.09
No. of reflections	2905
No. of parameters	245
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.31
Computer programs: APEX2 and SAINT (Bruker, 2004), SHELXT2016 (Sheldrick, 2015a), SHELXL2016 (Sheldrick, 2015b ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1583586

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314617015954/lh4027sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617015954/lh4027Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617015954/lh4027Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXT2016 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b) and PLATON (Spek, 2009).

2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium 3-carboxy-4-hydroxybenzenesulfonate monohydrate top

Crystal data top

C₄H₇N₃O⁺·C₇H₅O₆S⁻·H₂O	F(000) = 724
M_r = 348.31	D_x = 1.569 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 7.2459 (2) Å	Cell parameters from 9845 reflections
b = 15.5638 (4) Å	θ = 2.2–36.3°
c = 13.0774 (3) Å	µ = 2.42 mm⁻¹
β = 90.100 (1)°	T = 295 K
V = 1474.79 (7) Å³	Block, colourless
Z = 4	0.15 × 0.15 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	2798 reflections with I > 2σ(I)
ω and φ scans	R_int = 0.041
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θ_max = 72.9°, θ_min = 2.8°
T_min = 0.587, T_max = 0.754	h = −7→8
22225 measured reflections	k = −19→19
2905 independent reflections	l = −15→16

Refinement top

Refinement on F²	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.054P)² + 1.5916P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
2905 reflections	Δρ_max = 0.38 e Å⁻³
245 parameters	Δρ_min = −0.31 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.76216 (13)	0.74331 (4)	0.63421 (5)	0.0308 (2)
O2	1.2464 (5)	0.77212 (16)	0.70783 (19)	0.0483 (6)
O3	0.9162 (4)	0.79601 (15)	0.6001 (3)	0.0434 (7)
O4	0.7878 (6)	0.71354 (15)	0.73693 (17)	0.0672 (11)
O5	0.5909 (4)	0.78905 (16)	0.6167 (3)	0.0525 (8)
O6	0.7490 (6)	0.44174 (15)	0.36304 (17)	0.0575 (7)
H6A	0.750112	0.396763	0.395694	0.086*
O7	0.7467 (5)	0.34602 (13)	0.52820 (18)	0.0512 (6)
O8	0.7550 (6)	0.41124 (13)	0.67992 (17)	0.0506 (6)
H8	0.772633	0.362118	0.700399	0.076*
C1	0.7584 (5)	0.65219 (16)	0.55462 (19)	0.0269 (5)
C2	0.7543 (5)	0.57105 (16)	0.59708 (19)	0.0288 (5)
H2	0.754383	0.564915	0.667819	0.035*
C3	0.7500 (5)	0.49812 (16)	0.5351 (2)	0.0303 (6)
C4	0.7492 (7)	0.50885 (19)	0.4280 (2)	0.0369 (6)
C5	0.7545 (6)	0.5911 (2)	0.3871 (2)	0.0407 (7)
H5	0.757849	0.597882	0.316487	0.049*
C6	0.7550 (6)	0.66220 (18)	0.4484 (2)	0.0357 (6)
H6	0.752994	0.716846	0.419590	0.043*
C7	0.7485 (7)	0.41139 (18)	0.5798 (2)	0.0363 (6)
N1A	1.1347 (5)	1.0238 (3)	0.3774 (3)	0.0284 (7)	0.771 (3)
H1A	1.111783	1.077990	0.375202	0.034*	0.771 (3)
C2A	1.0054 (5)	0.9613 (3)	0.3817 (4)	0.0302 (7)	0.771 (3)
C3A	1.1079 (7)	0.8776 (3)	0.3811 (4)	0.0314 (8)	0.771 (3)
H3A	1.059443	0.822297	0.379979	0.038*	0.771 (3)
N4A	1.3000 (7)	0.9033 (2)	0.3826 (3)	0.0235 (7)	0.771 (3)
C5A	1.3095 (7)	0.9879 (3)	0.3770 (4)	0.0257 (8)	0.771 (3)
O6A	0.8414 (4)	0.9749 (2)	0.3856 (3)	0.0454 (7)	0.771 (3)
C6A	1.4533 (7)	0.8455 (3)	0.3792 (6)	0.0456 (14)	0.771 (3)
H6AA	1.409585	0.787429	0.384815	0.068*	0.771 (3)
H6AB	1.517571	0.852489	0.315673	0.068*	0.771 (3)
H6AC	1.535550	0.857697	0.434992	0.068*	0.771 (3)
N8A	1.4596 (6)	1.0336 (2)	0.3736 (4)	0.0362 (8)	0.771 (3)
H8AA	1.565543	1.008656	0.374992	0.043*	0.771 (3)
H8AB	1.452993	1.088636	0.369915	0.043*	0.771 (3)
N1B	1.359 (2)	1.0233 (11)	0.3762 (13)	0.0284 (7)	0.229 (3)
H1B	1.378647	1.077807	0.373429	0.034*	0.229 (3)
C2B	1.5042 (18)	0.9616 (9)	0.3808 (14)	0.0302 (7)	0.229 (3)
C3B	1.399 (3)	0.8786 (14)	0.3735 (15)	0.0314 (8)	0.229 (3)
H3B	1.447922	0.823430	0.370289	0.038*	0.229 (3)
N4B	1.210 (3)	0.9018 (9)	0.3724 (13)	0.0235 (7)	0.229 (3)
C5B	1.194 (3)	0.9897 (11)	0.3766 (14)	0.0257 (8)	0.229 (3)
O6B	1.6597 (13)	0.9739 (8)	0.3906 (12)	0.0454 (7)	0.229 (3)
C6B	1.059 (3)	0.8509 (12)	0.358 (2)	0.0456 (14)	0.229 (3)
H6BA	1.095917	0.791695	0.356864	0.068*	0.229 (3)
H6BB	0.972351	0.860018	0.412162	0.068*	0.229 (3)
H6BC	1.001645	0.865178	0.293577	0.068*	0.229 (3)
N8B	1.025 (2)	1.0332 (8)	0.3690 (14)	0.0362 (8)	0.229 (3)
H8BA	1.023308	1.088293	0.363335	0.043*	0.229 (3)
H8BB	0.923017	1.004941	0.369984	0.043*	0.229 (3)
H2A	1.340 (4)	0.768 (3)	0.672 (3)	0.054*
H2B	1.191 (5)	0.789 (3)	0.657 (2)	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0428 (4)	0.0216 (3)	0.0280 (3)	0.0009 (4)	0.0022 (5)	−0.0013 (2)
O2	0.0439 (15)	0.0468 (12)	0.0543 (14)	0.0027 (15)	−0.0050 (17)	−0.0055 (11)
O3	0.0402 (15)	0.0318 (12)	0.0583 (18)	−0.0089 (10)	0.0060 (12)	−0.0053 (12)
O4	0.142 (3)	0.0337 (12)	0.0260 (11)	−0.0063 (18)	−0.0006 (18)	−0.0024 (9)
O5	0.0366 (14)	0.0385 (13)	0.082 (2)	0.0052 (10)	0.0110 (16)	−0.0179 (16)
O6	0.090 (2)	0.0438 (12)	0.0386 (12)	−0.0018 (18)	−0.007 (2)	−0.0200 (9)
O7	0.0671 (17)	0.0275 (10)	0.0591 (13)	−0.0055 (14)	0.0019 (18)	−0.0112 (9)
O8	0.0783 (19)	0.0285 (10)	0.0449 (12)	−0.0075 (17)	−0.013 (2)	0.0040 (9)
C1	0.0286 (14)	0.0273 (12)	0.0247 (11)	0.0052 (15)	−0.0008 (15)	−0.0021 (9)
C2	0.0339 (15)	0.0275 (12)	0.0248 (11)	−0.0037 (15)	0.0047 (16)	−0.0015 (9)
C3	0.0307 (15)	0.0262 (12)	0.0341 (13)	−0.0005 (15)	−0.0032 (17)	−0.0051 (10)
C4	0.0410 (17)	0.0368 (14)	0.0329 (13)	−0.0015 (18)	0.0039 (18)	−0.0137 (11)
C5	0.0520 (19)	0.0461 (16)	0.0239 (12)	−0.0007 (19)	0.002 (2)	−0.0032 (11)
C6	0.0460 (18)	0.0325 (14)	0.0285 (12)	−0.0022 (18)	−0.0018 (18)	0.0041 (10)
C7	0.0371 (16)	0.0292 (13)	0.0424 (14)	0.003 (2)	−0.0048 (19)	−0.0046 (11)
N1A	0.021 (2)	0.0292 (17)	0.0350 (17)	0.0047 (14)	0.0027 (18)	0.0010 (14)
C2A	0.0217 (17)	0.0411 (19)	0.0278 (16)	0.0029 (16)	0.0037 (18)	−0.0009 (14)
C3A	0.022 (2)	0.039 (2)	0.033 (2)	−0.0025 (19)	0.001 (2)	−0.0029 (17)
N4A	0.015 (2)	0.0257 (12)	0.0300 (16)	−0.0022 (17)	−0.0043 (18)	−0.0005 (11)
C5A	0.026 (2)	0.0278 (18)	0.0236 (15)	0.0034 (18)	0.003 (2)	0.0022 (14)
O6A	0.0203 (14)	0.0618 (18)	0.0543 (17)	0.0007 (14)	0.0050 (16)	0.0023 (14)
C6A	0.029 (2)	0.029 (2)	0.079 (4)	0.0078 (19)	−0.007 (3)	−0.008 (2)
N8A	0.0251 (19)	0.0283 (15)	0.055 (2)	0.0015 (14)	0.001 (2)	0.0031 (15)
N1B	0.021 (2)	0.0292 (17)	0.0350 (17)	0.0047 (14)	0.0027 (18)	0.0010 (14)
C2B	0.0217 (17)	0.0411 (19)	0.0278 (16)	0.0029 (16)	0.0037 (18)	−0.0009 (14)
C3B	0.022 (2)	0.039 (2)	0.033 (2)	−0.0025 (19)	0.001 (2)	−0.0029 (17)
N4B	0.015 (2)	0.0257 (12)	0.0300 (16)	−0.0022 (17)	−0.0043 (18)	−0.0005 (11)
C5B	0.026 (2)	0.0278 (18)	0.0236 (15)	0.0034 (18)	0.003 (2)	0.0022 (14)
O6B	0.0203 (14)	0.0618 (18)	0.0543 (17)	0.0007 (14)	0.0050 (16)	0.0023 (14)
C6B	0.029 (2)	0.029 (2)	0.079 (4)	0.0078 (19)	−0.007 (3)	−0.008 (2)
N8B	0.0251 (19)	0.0283 (15)	0.055 (2)	0.0015 (14)	0.001 (2)	0.0031 (15)

Geometric parameters (Å, º) top

S1—O4	1.433 (2)	C3A—N4A	1.448 (6)
S1—O5	1.448 (3)	C3A—H3A	0.9300
S1—O3	1.456 (3)	N4A—C5A	1.321 (6)
S1—C1	1.759 (3)	N4A—C6A	1.430 (6)
O2—H2A	0.824 (10)	C5A—N8A	1.300 (7)
O2—H2B	0.819 (10)	C6A—H6AA	0.9600
O6—C4	1.347 (3)	C6A—H6AB	0.9600
O6—H6A	0.8200	C6A—H6AC	0.9600
O7—C7	1.221 (4)	N8A—H8AA	0.8600
O8—C7	1.310 (4)	N8A—H8AB	0.8600
O8—H8	0.8200	N1B—C5B	1.31 (3)
C1—C2	1.380 (3)	N1B—C2B	1.42 (2)
C1—C6	1.399 (3)	N1B—H1B	0.8600
C2—C3	1.395 (3)	C2B—O6B	1.150 (17)
C2—H2	0.9300	C2B—C3B	1.50 (2)
C3—C4	1.411 (4)	C3B—N4B	1.42 (2)
C3—C7	1.471 (4)	C3B—H3B	0.9300
C4—C5	1.387 (4)	N4B—C6B	1.36 (2)
C5—C6	1.367 (4)	N4B—C5B	1.37 (2)
C5—H5	0.9300	C5B—N8B	1.40 (2)
C6—H6	0.9300	C6B—H6BA	0.9600
N1A—C2A	1.351 (6)	C6B—H6BB	0.9600
N1A—C5A	1.384 (6)	C6B—H6BC	0.9600
N1A—H1A	0.8600	N8B—H8BA	0.8600
C2A—O6A	1.208 (5)	N8B—H8BB	0.8600
C2A—C3A	1.499 (6)

O4—S1—O5	114.6 (2)	C5A—N4A—C6A	125.8 (5)
O4—S1—O3	111.8 (2)	C5A—N4A—C3A	108.9 (5)
O5—S1—O3	109.37 (15)	C6A—N4A—C3A	125.0 (4)
O4—S1—C1	107.21 (13)	N8A—C5A—N4A	126.2 (5)
O5—S1—C1	106.87 (18)	N8A—C5A—N1A	123.0 (4)
O3—S1—C1	106.50 (16)	N4A—C5A—N1A	110.8 (5)
H2A—O2—H2B	88 (4)	N4A—C6A—H6AA	109.5
C4—O6—H6A	109.5	N4A—C6A—H6AB	109.5
C7—O8—H8	109.5	H6AA—C6A—H6AB	109.5
C2—C1—C6	120.1 (2)	N4A—C6A—H6AC	109.5
C2—C1—S1	120.00 (19)	H6AA—C6A—H6AC	109.5
C6—C1—S1	119.9 (2)	H6AB—C6A—H6AC	109.5
C1—C2—C3	120.8 (2)	C5A—N8A—H8AA	120.0
C1—C2—H2	119.6	C5A—N8A—H8AB	120.0
C3—C2—H2	119.6	H8AA—N8A—H8AB	120.0
C2—C3—C4	118.7 (2)	C5B—N1B—C2B	113.9 (17)
C2—C3—C7	121.1 (2)	C5B—N1B—H1B	123.0
C4—C3—C7	120.2 (2)	C2B—N1B—H1B	123.0
O6—C4—C5	118.1 (3)	O6B—C2B—N1B	128.0 (16)
O6—C4—C3	122.3 (3)	O6B—C2B—C3B	130.3 (17)
C5—C4—C3	119.5 (2)	N1B—C2B—C3B	101.7 (15)
C6—C5—C4	121.4 (3)	N4B—C3B—C2B	105.8 (19)
C6—C5—H5	119.3	N4B—C3B—H3B	127.1
C4—C5—H5	119.3	C2B—C3B—H3B	127.1
C5—C6—C1	119.5 (3)	C6B—N4B—C5B	121.0 (18)
C5—C6—H6	120.3	C6B—N4B—C3B	129.0 (15)
C1—C6—H6	120.3	C5B—N4B—C3B	109.6 (19)
O7—C7—O8	123.4 (3)	N1B—C5B—N4B	109 (2)
O7—C7—C3	123.1 (3)	N1B—C5B—N8B	127.2 (15)
O8—C7—C3	113.5 (2)	N4B—C5B—N8B	123.6 (17)
C2A—N1A—C5A	110.1 (5)	N4B—C6B—H6BA	109.5
C2A—N1A—H1A	124.9	N4B—C6B—H6BB	109.5
C5A—N1A—H1A	124.9	H6BA—C6B—H6BB	109.5
O6A—C2A—N1A	123.9 (4)	N4B—C6B—H6BC	109.5
O6A—C2A—C3A	129.7 (4)	H6BA—C6B—H6BC	109.5
N1A—C2A—C3A	106.4 (4)	H6BB—C6B—H6BC	109.5
N4A—C3A—C2A	103.7 (4)	C5B—N8B—H8BA	120.0
N4A—C3A—H3A	128.2	C5B—N8B—H8BB	120.0
C2A—C3A—H3A	128.2	H8BA—N8B—H8BB	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O3	0.82 (1)	2.13 (3)	2.799 (4)	139 (4)
O6—H6A···O7	0.82	1.90	2.624 (3)	146
N1A—H1A···O3ⁱ	0.86	2.00	2.844 (5)	168
O2—H2A···O5ⁱⁱ	0.82 (1)	1.99 (2)	2.780 (4)	161 (5)
N8A—H8AA···O6Aⁱⁱ	0.86	2.07	2.917 (5)	168
N8A—H8AB···O5ⁱ	0.86	1.94	2.788 (4)	170
O8—H8···O2ⁱⁱⁱ	0.82	1.85	2.616 (3)	155
C6A—H6AB···O4^iv	0.96	2.44	3.194 (7)	135

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

Acknowledgements

The authors acknowledge the SAIF, IIT, Madras for the data collection.

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