4-Nitro­anilinium 3-carb­oxy-4-hy­droxy­benzene­sulfonate monohydrate

Sivakumar, P.K.; Kumar, M.K.; Chakkaravarthi, G.; Kumar, R.M.; Kanagadurai, R.

doi:10.1107/S1600536813026779

organic compounds

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Volume 69| Part 11| November 2013| Page o1609

doi:10.1107/S1600536813026779

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4-Nitroanilinium 3-carboxy-4-hydroxybenzenesulfonate monohydrate

P. K. Sivakumar,^a M. Krishna Kumar,^b G. Chakkaravarthi,^c ^* R. Mohan Kumar ^b and R. Kanagadurai ^b ^*

^aDepartment of Physics, M. N. M. Jain Engineering College, Chennai 600 097, India, ^bDepartment of Physics, Presidency College, Chennai 600 005, India, and ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, srkanagadurai@yahoo.co.in

(Received 22 September 2013; accepted 29 September 2013; online 5 October 2013)

In the title hydrated salt, C₆H₇N₂O₂⁺·C₇H₅O₆S⁻·H₂O, the benzene ring of the cation makes a dihedral angle of 1.32 (19)° with the attached nitro group. In the anion, an intramolecular O—H⋯O hydrogen bond with an S(6) ring motif is formed between the carboxyl and hydroxy groups; the dihedral angle between the carboxyl group and the benzene ring is 8.76 (8)°. The crystal structure exhibits intermolecular N—H⋯O, O—H⋯O, C—H⋯O, and π–π [centroid–centroid distances = 3.6634 (9) and 3.7426 (9) Å] interactions to form a three-dimensional network.

CCDC reference: 963644

Related literature

For molecular compounds with nonlinear optical properties, see: Nalwa & Miyata (1997 ). For related structures, see: Asiri et al. (2010 ); Krishnakumar et al. (2012 ); Sudhahar et al. (2013 ).

Experimental

Crystal data

C₆H₇N₂O₂⁺·C₇H₅O₆S⁻·H₂O
M_r = 374.32
Orthorhombic, P b c a
a = 13.2676 (3) Å
b = 13.5572 (3) Å
c = 17.1246 (4) Å
V = 3080.23 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 295 K
0.26 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.934, T_max = 0.949
15578 measured reflections
3640 independent reflections
3062 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.107
S = 1.03
3640 reflections
236 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O9	0.89	1.99	2.841 (2)	160
N1—H1B⋯O1	0.89	1.95	2.8357 (18)	171
O4—H4A⋯O5	0.82	1.88	2.6028 (18)	146
C9—H9⋯O9	0.93	2.57	3.141 (3)	121
N1—H1A⋯O7ⁱ	0.89	2.40	2.836 (2)	111
N1—H1C⋯O2ⁱⁱ	0.89	1.93	2.8069 (18)	168
O4—H4A⋯O2ⁱⁱⁱ	0.82	2.38	2.9494 (16)	128
O6—H6⋯O3^iv	0.82	1.86	2.6595 (17)	164
O9—H9A⋯O2^v	0.82 (1)	2.33 (3)	3.005 (2)	139 (4)
O9—H9A⋯O3^v	0.82 (1)	2.48 (3)	3.151 (2)	140 (4)
O9—H9B⋯O4^vi	0.82 (1)	2.56 (3)	3.283 (2)	149 (4)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+1; (iii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (vi) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 963644

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813026779/is5308sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813026779/is5308Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813026779/is5308Isup3.cml

checkCIF report

Comment top

In continuation of our studies of molecular compounds with non-linear optical properties which are used in optoelectronic and photonic devices (Nalwa & Miyata, 1997), we herewith report the crystal structure of the title compound (I), (Fig. 1). The title compound consists of one C₆H₇N₂O₂⁺ cation, one C₇H₅O₆S^- anion and a water molecule in the asymmetric unit. The geometric parameters of the title compound are comparable with the reported structures (Asiri et al., 2010; Krishnakumar et al., 2012; Sudhahar et al., 2013).

The dihedral angle between the two benzene rings (C1–C6) and (C8–C13) is 8.18 (7)°. The benzene ring (C1–C6) is planar [r.m.s. deviation = 0.0152 (17) Å] and makes a dihedral angle of 1.32 (19)° with the attached nitro group. The mean plane of carboxy group is inclined at an angle of 8.76 (8)° with the planar [r.m.s. deviation = 0.0137 (16) Å] benzene ring (C8–C13) of anion.

The crystal structure exhibits intermolecular N—H···O, O—H···O, C—H···O hydrogen bonds (Table 1 & Fig. 2) and π–π interactions [[Cg1···Cg2 = 3.7426 (9)Å, Cg1···Cg2ⁱ = 3.6634 (9) Å; (i) 1/2-x, 1/2+y, z; Cg1 and Cg2 are the centroids of the rings (C1–C6) and (C8–C13), respectively] to form a three-dimensional molecular arrangement.

Related literature top

For molecular compounds with nonlinear optical properties, see: Nalwa & Miyata (1997). For related structures, see: Asiri et al. (2010); Krishnakumar et al. (2012); Sudhahar et al. (2013).

Experimental top

The title compound was synthesized in ethanol by using 4-nitroaniline (6.90 g) and 5-sulfosalicylic acid dihydrate (12.711 g) in equimolar ratio. The saturated solution was allowed to evaporating slowly at room temperature. After the evaporation period of three weeks the crystals were collected and used for X-ray data collection.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of the title compound, viewed down the b axis. Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

4-Nitrobenzeneaminium 3-carboxy-4-hydroxybenzenesulfonate monohydrate top

Crystal data top

C₆H₇N₂O₂⁺·C₇H₅O₆S⁻·H₂O	F(000) = 1552
M_r = 374.32	D_x = 1.614 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3844 reflections
a = 13.2676 (3) Å	θ = 2.4–28.4°
b = 13.5572 (3) Å	µ = 0.27 mm⁻¹
c = 17.1246 (4) Å	T = 295 K
V = 3080.23 (12) Å³	Block, colourless
Z = 8	0.26 × 0.24 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3640 independent reflections
Radiation source: fine-focus sealed tube	3062 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and ϕ scan	θ_max = 28.4°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→11
T_min = 0.934, T_max = 0.949	k = −18→12
15578 measured reflections	l = −22→17

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0571P)² + 1.2353P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3640 reflections	Δρ_max = 0.44 e Å⁻³
236 parameters	Δρ_min = −0.34 e Å⁻³
2 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: 0.0019 (4)

Crystal data top

C₆H₇N₂O₂⁺·C₇H₅O₆S⁻·H₂O	V = 3080.23 (12) Å³
M_r = 374.32	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.2676 (3) Å	µ = 0.27 mm⁻¹
b = 13.5572 (3) Å	T = 295 K
c = 17.1246 (4) Å	0.26 × 0.24 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3640 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3062 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.949	R_int = 0.024
15578 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	2 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.44 e Å⁻³
3640 reflections	Δρ_min = −0.34 e Å⁻³
236 parameters

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.

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

	x	y	z	U_iso*/U_eq
C1	0.23376 (11)	0.22732 (11)	0.36435 (9)	0.0324 (3)
H1	0.1676	0.2374	0.3805	0.039*
C2	0.31016 (11)	0.22696 (11)	0.41813 (9)	0.0291 (3)
H2	0.2958	0.2364	0.4708	0.035*
C3	0.41012 (10)	0.21236 (10)	0.39384 (8)	0.0249 (3)
C4	0.43237 (10)	0.20070 (10)	0.31573 (8)	0.0267 (3)
H4	0.4989	0.1928	0.2998	0.032*
C5	0.35471 (11)	0.20079 (11)	0.26038 (8)	0.0277 (3)
C6	0.25490 (11)	0.21266 (11)	0.28527 (9)	0.0304 (3)
C7	0.37580 (12)	0.18773 (12)	0.17625 (9)	0.0343 (3)
C8	0.10072 (13)	−0.02919 (13)	0.38844 (10)	0.0402 (4)
H8	0.0307	−0.0320	0.3888	0.048*
C9	0.15443 (12)	−0.02301 (13)	0.45736 (9)	0.0371 (4)
H9	0.1210	−0.0220	0.5051	0.045*
C10	0.25815 (12)	−0.01838 (11)	0.45470 (9)	0.0301 (3)
C11	0.31058 (12)	−0.02335 (11)	0.38520 (10)	0.0359 (4)
H11	0.3807	−0.0228	0.3848	0.043*
C12	0.25710 (13)	−0.02920 (12)	0.31634 (10)	0.0391 (4)
H12	0.2905	−0.0319	0.2686	0.047*
C13	0.15317 (13)	−0.03101 (12)	0.31948 (9)	0.0361 (4)
N1	0.31299 (10)	−0.00774 (10)	0.52813 (8)	0.0351 (3)
H1A	0.2733	0.0208	0.5634	0.053*
H1B	0.3674	0.0294	0.5205	0.053*
H1C	0.3317	−0.0670	0.5452	0.053*
N2	0.09540 (14)	−0.03548 (12)	0.24631 (9)	0.0513 (4)
O1	0.47752 (9)	0.12506 (9)	0.51725 (7)	0.0434 (3)
O2	0.59937 (8)	0.18656 (10)	0.42481 (7)	0.0403 (3)
O3	0.50743 (9)	0.30034 (8)	0.50523 (7)	0.0391 (3)
O4	0.17634 (9)	0.21175 (11)	0.23553 (7)	0.0485 (4)
H4A	0.1969	0.2027	0.1909	0.073*
O5	0.30993 (9)	0.17648 (13)	0.12778 (7)	0.0580 (4)
O6	0.47157 (9)	0.18949 (11)	0.15782 (7)	0.0489 (3)
H6	0.4778	0.1818	0.1106	0.073*
O7	0.14092 (17)	−0.03731 (18)	0.18586 (9)	0.1005 (8)
O8	0.00426 (13)	−0.03699 (16)	0.24947 (10)	0.0834 (6)
O9	0.16700 (15)	0.10629 (14)	0.60925 (13)	0.0740 (5)
S1	0.50511 (2)	0.20521 (3)	0.46557 (2)	0.02593 (12)
H9A	0.152 (3)	0.149 (2)	0.5775 (18)	0.143 (16)*
H9B	0.186 (3)	0.136 (3)	0.6481 (16)	0.167 (19)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0208 (7)	0.0399 (8)	0.0365 (8)	0.0032 (6)	0.0027 (6)	−0.0022 (6)
C2	0.0273 (7)	0.0328 (7)	0.0273 (7)	0.0014 (6)	0.0032 (6)	−0.0012 (6)
C3	0.0228 (7)	0.0278 (7)	0.0240 (7)	−0.0001 (5)	−0.0020 (5)	0.0014 (5)
C4	0.0208 (6)	0.0333 (7)	0.0260 (7)	0.0000 (5)	0.0008 (5)	0.0018 (6)
C5	0.0250 (7)	0.0336 (7)	0.0245 (7)	−0.0008 (6)	−0.0022 (5)	0.0009 (6)
C6	0.0227 (7)	0.0364 (8)	0.0323 (8)	0.0010 (6)	−0.0050 (6)	0.0002 (6)
C7	0.0281 (8)	0.0483 (9)	0.0266 (7)	−0.0008 (6)	−0.0025 (6)	0.0017 (7)
C8	0.0297 (8)	0.0515 (10)	0.0396 (9)	−0.0019 (7)	−0.0032 (7)	0.0014 (7)
C9	0.0310 (8)	0.0503 (10)	0.0301 (8)	−0.0037 (7)	0.0030 (6)	0.0015 (7)
C10	0.0304 (8)	0.0277 (7)	0.0322 (7)	−0.0013 (6)	−0.0031 (6)	0.0043 (6)
C11	0.0295 (8)	0.0346 (8)	0.0436 (9)	−0.0011 (6)	0.0052 (7)	0.0011 (7)
C12	0.0455 (9)	0.0387 (8)	0.0332 (8)	−0.0023 (7)	0.0086 (7)	0.0014 (7)
C13	0.0426 (9)	0.0348 (8)	0.0307 (8)	−0.0011 (7)	−0.0049 (7)	0.0024 (6)
N1	0.0306 (7)	0.0385 (7)	0.0362 (7)	−0.0016 (5)	−0.0047 (5)	0.0027 (6)
N2	0.0630 (11)	0.0556 (10)	0.0354 (8)	−0.0016 (8)	−0.0099 (7)	0.0018 (7)
O1	0.0402 (6)	0.0507 (7)	0.0394 (6)	−0.0103 (5)	−0.0074 (5)	0.0197 (6)
O2	0.0242 (5)	0.0657 (8)	0.0310 (6)	0.0081 (5)	0.0021 (4)	0.0055 (5)
O3	0.0451 (7)	0.0419 (7)	0.0302 (6)	−0.0013 (5)	−0.0072 (5)	−0.0047 (5)
O4	0.0238 (6)	0.0848 (10)	0.0370 (7)	0.0052 (6)	−0.0083 (5)	−0.0074 (6)
O5	0.0323 (7)	0.1114 (12)	0.0304 (6)	−0.0045 (7)	−0.0071 (5)	−0.0088 (7)
O6	0.0289 (6)	0.0934 (10)	0.0243 (6)	−0.0025 (6)	0.0010 (5)	0.0018 (6)
O7	0.0957 (14)	0.176 (2)	0.0304 (8)	−0.0207 (14)	−0.0011 (8)	0.0029 (10)
O8	0.0567 (11)	0.1344 (19)	0.0590 (10)	0.0062 (10)	−0.0251 (8)	−0.0088 (11)
O9	0.0787 (12)	0.0606 (10)	0.0827 (13)	0.0281 (9)	−0.0161 (10)	−0.0100 (10)
S1	0.0221 (2)	0.0348 (2)	0.02094 (19)	−0.00090 (13)	−0.00073 (12)	0.00349 (13)

Geometric parameters (Å, º) top

C1—C2	1.370 (2)	C10—C11	1.380 (2)
C1—C6	1.397 (2)	C10—N1	1.4599 (19)
C1—H1	0.9300	C11—C12	1.378 (2)
C2—C3	1.4040 (19)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.380 (2)
C3—C4	1.379 (2)	C12—H12	0.9300
C3—S1	1.7625 (14)	C13—N2	1.470 (2)
C4—C5	1.400 (2)	N1—H1A	0.8900
C4—H4	0.9300	N1—H1B	0.8900
C5—C6	1.400 (2)	N1—H1C	0.8900
C5—C7	1.478 (2)	N2—O7	1.199 (2)
C6—O4	1.3462 (18)	N2—O8	1.211 (2)
C7—O5	1.2150 (19)	O1—S1	1.4484 (12)
C7—O6	1.309 (2)	O2—S1	1.4544 (11)
C8—C13	1.371 (2)	O3—S1	1.4579 (12)
C8—C9	1.381 (2)	O4—H4A	0.8200
C8—H8	0.9300	O6—H6	0.8200
C9—C10	1.378 (2)	O9—H9A	0.821 (10)
C9—H9	0.9300	O9—H9B	0.815 (10)

C2—C1—C6	120.18 (13)	C11—C10—N1	119.75 (14)
C2—C1—H1	119.9	C12—C11—C10	118.75 (15)
C6—C1—H1	119.9	C12—C11—H11	120.6
C1—C2—C3	120.03 (13)	C10—C11—H11	120.6
C1—C2—H2	120.0	C11—C12—C13	118.81 (15)
C3—C2—H2	120.0	C11—C12—H12	120.6
C4—C3—C2	120.39 (13)	C13—C12—H12	120.6
C4—C3—S1	121.11 (11)	C8—C13—C12	122.71 (16)
C2—C3—S1	118.47 (11)	C8—C13—N2	118.05 (16)
C3—C4—C5	119.94 (13)	C12—C13—N2	119.24 (16)
C3—C4—H4	120.0	C10—N1—H1A	109.5
C5—C4—H4	120.0	C10—N1—H1B	109.5
C4—C5—C6	119.34 (13)	H1A—N1—H1B	109.5
C4—C5—C7	121.36 (13)	C10—N1—H1C	109.5
C6—C5—C7	119.30 (13)	H1A—N1—H1C	109.5
O4—C6—C1	117.34 (13)	H1B—N1—H1C	109.5
O4—C6—C5	122.58 (14)	O7—N2—O8	122.79 (19)
C1—C6—C5	120.08 (13)	O7—N2—C13	118.31 (19)
O5—C7—O6	122.38 (15)	O8—N2—C13	118.91 (17)
O5—C7—C5	123.01 (15)	C6—O4—H4A	109.5
O6—C7—C5	114.61 (13)	C7—O6—H6	109.5
C13—C8—C9	118.38 (16)	H9A—O9—H9B	106 (4)
C13—C8—H8	120.8	O1—S1—O2	112.34 (7)
C9—C8—H8	120.8	O1—S1—O3	112.60 (8)
C10—C9—C8	119.32 (15)	O2—S1—O3	111.05 (7)
C10—C9—H9	120.3	O1—S1—C3	106.64 (7)
C8—C9—H9	120.3	O2—S1—C3	106.86 (7)
C9—C10—C11	121.97 (15)	O3—S1—C3	106.93 (7)
C9—C10—N1	118.28 (14)

C6—C1—C2—C3	0.3 (2)	C8—C9—C10—N1	177.48 (15)
C1—C2—C3—C4	1.6 (2)	C9—C10—C11—C12	2.6 (2)
C1—C2—C3—S1	−176.32 (11)	N1—C10—C11—C12	−177.29 (14)
C2—C3—C4—C5	−1.7 (2)	C10—C11—C12—C13	−0.7 (2)
S1—C3—C4—C5	176.15 (10)	C9—C8—C13—C12	1.5 (3)
C3—C4—C5—C6	−0.1 (2)	C9—C8—C13—N2	−178.74 (15)
C3—C4—C5—C7	−179.54 (14)	C11—C12—C13—C8	−1.3 (3)
C2—C1—C6—O4	178.63 (14)	C11—C12—C13—N2	178.93 (14)
C2—C1—C6—C5	−2.1 (2)	C8—C13—N2—O7	−179.8 (2)
C4—C5—C6—O4	−178.81 (14)	C12—C13—N2—O7	−0.1 (3)
C7—C5—C6—O4	0.7 (2)	C8—C13—N2—O8	0.3 (3)
C4—C5—C6—C1	2.0 (2)	C12—C13—N2—O8	−179.96 (18)
C7—C5—C6—C1	−178.55 (14)	C4—C3—S1—O1	−120.21 (13)
C4—C5—C7—O5	171.57 (17)	C2—C3—S1—O1	57.67 (13)
C6—C5—C7—O5	−7.9 (3)	C4—C3—S1—O2	0.12 (14)
C4—C5—C7—O6	−8.6 (2)	C2—C3—S1—O2	178.00 (11)
C6—C5—C7—O6	171.95 (14)	C4—C3—S1—O3	119.10 (12)
C13—C8—C9—C10	0.3 (3)	C2—C3—S1—O3	−63.02 (13)
C8—C9—C10—C11	−2.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O9	0.89	1.99	2.841 (2)	160
N1—H1B···O1	0.89	1.95	2.8357 (18)	171
O4—H4A···O5	0.82	1.88	2.6028 (18)	146
C9—H9···O9	0.93	2.57	3.141 (3)	121
N1—H1A···O7ⁱ	0.89	2.40	2.836 (2)	111
N1—H1C···O2ⁱⁱ	0.89	1.93	2.8069 (18)	168
O4—H4A···O2ⁱⁱⁱ	0.82	2.38	2.9494 (16)	128
O6—H6···O3^iv	0.82	1.86	2.6595 (17)	164
O9—H9A···O2^v	0.82 (1)	2.33 (3)	3.005 (2)	139 (4)
O9—H9A···O3^v	0.82 (1)	2.48 (3)	3.151 (2)	140 (4)
O9—H9B···O4^vi	0.82 (1)	2.56 (3)	3.283 (2)	149 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O9	0.89	1.99	2.841 (2)	160
N1—H1B···O1	0.89	1.95	2.8357 (18)	171
O4—H4A···O5	0.82	1.88	2.6028 (18)	146
C9—H9···O9	0.93	2.57	3.141 (3)	121
N1—H1A···O7ⁱ	0.89	2.40	2.836 (2)	111
N1—H1C···O2ⁱⁱ	0.89	1.93	2.8069 (18)	168
O4—H4A···O2ⁱⁱⁱ	0.82	2.38	2.9494 (16)	128
O6—H6···O3^iv	0.82	1.86	2.6595 (17)	164
O9—H9A···O2^v	0.821 (10)	2.33 (3)	3.005 (2)	139 (4)
O9—H9A···O3^v	0.821 (10)	2.48 (3)	3.151 (2)	140 (4)
O9—H9B···O4^vi	0.815 (10)	2.56 (3)	3.283 (2)	149 (4)

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

Acknowledgements

The authors thank SAIF, IIT, Madras, for the data collection. MKK thanks the Council of Scientific and Industrial Research, New Delhi, India, for providing financial support [project No.03 (1200)/11/EMR-II].

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