Crystal structure of 4-(di­methyl­amino)­pyridinium 4-amino­benzoate dihydrate

Thirunavukkarasu, A.; Silambarasan, A.; Kumar, R.M.; Umarani, P.R.; Chakkaravarthi, G.

doi:10.1107/S2056989014026310

organic compounds

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Volume 71| Part 1| January 2015| Pages o26-o27

https://doi.org/10.1107/S2056989014026310

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Crystal structure of 4-(dimethylamino)pyridinium 4-aminobenzoate dihydrate

A. Thirunavukkarasu,^a A. Silambarasan,^a R. Mohan Kumar,^a P. R. Umarani ^b ^* and G. Chakkaravarthi ^c ^*

^aDepartment of Physics, Presidency College, Chennai 600 005, India, ^bDirectorate of Collegiate Education, Govt. of Tamil Nadu, Chennai 600 006, India, and ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: kan_uma6@yahoo.com, chakkaravarthi_2005@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 29 November 2014; accepted 30 November 2014; online 1 January 2015)

In the title hydrated molecular salt, C₇H₁₁N₂⁺·C₇H₆NO₂⁻·2H₂O, the cation is protonated at the pyridine N atom and the dihedral angle between the benzene ring and the CO₂⁻ group in the anion is 8.5 (2)°. In the crystal, the cation forms an N—H⋯O hydrogen bond to the anion and the anion forms two N—H⋯O hydrogen bonds to adjacent water molecules. Both water molecules form two O—H⋯O hydrogen bonds to carboxylate O atoms. In combination, these hydrogen bonds generate a three-dimensional network and two weak C—H⋯π interactions are also observed.

Keywords: crystal structure; 4-(dimethylamino)pyridinium; 4-aminobenzoate; hydrate; hydrogen bonding.

CCDC reference: 1036769

1. Related literature

For related structures, see: Dhanabalan et al. (2014 ); Lo & Ng (2008 ); Pereira Silva et al. (2010 ); Sivakumar et al. (2014 ).

2. Experimental

2.1. Crystal data

C₇H₁₁N₂⁺·C₇H₆NO₂⁻·2H₂O
M_r = 295.34
Triclinic, $[P \overline 1]$
a = 9.3402 (7) Å
b = 9.7999 (7) Å
c = 10.2132 (8) Å
α = 65.755 (3)°
β = 69.983 (2)°
γ = 89.212 (3)°
V = 792.08 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.30 × 0.24 × 0.20 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.973, T_max = 0.982
16983 measured reflections
3337 independent reflections
2141 reflections with I > 2σ(I)
R_int = 0.025

2.3. Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.168
S = 1.03
3337 reflections
216 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3ⁱ	0.87 (1)	2.04 (1)	2.898 (3)	167 (2)
N1—H1B⋯O4ⁱ	0.89 (1)	2.04 (1)	2.921 (3)	174 (2)
N2—H2A⋯O1ⁱⁱ	0.89 (1)	1.81 (1)	2.697 (2)	174 (2)
O3—H3A⋯O2ⁱⁱⁱ	0.83 (1)	2.03 (1)	2.858 (3)	175 (4)
O3—H3B⋯O1^iv	0.83 (1)	2.04 (1)	2.861 (3)	174 (4)
O4—H4A⋯O2^v	0.82 (1)	2.01 (1)	2.834 (3)	175 (4)
O4—H4B⋯O1^vi	0.82 (1)	2.04 (1)	2.847 (3)	167 (4)
C9—H9⋯Cg2^vii	0.93	2.80	3.510 (3)	134
C12—H12⋯Cg2ⁱ	0.93	2.84	3.535 (3)	132
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y-1, z+1; (iii) -x+1, -y+2, -z; (iv) x+1, y, z; (v) x, y, z+1; (vi) -x+1, -y+2, -z+1; (vii) -x, -y+1, -z+1.

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: 1036769

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989014026310/hb7333sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989014026310/hb7333Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989014026310/hb7333Isup3.cml

checkCIF report

Chemical context top

We hereby report the synthesis and crystal structure of the title compound (I), prepared by the reaction of 4-dimethylaminopyridine with 4-aminobenzoic acid in distilled water as solvent.

Structural commentary top

The geometric parameters of the title compound (I) (Fig.1) are comparable with the reported structures [Dhanabalan et al., 2014; Lo & Ng (2008); Pereira Silva et al., 2010; Sivakumar et al., 2014]. The 4-dimethylaminopyridinium cation is protonated at pyridine N2 atom, with the plane of the hetro atoms N(CH3)2 (N3/C13/C14) is inclined to the pyridine ring by 4.7 (2)°. In the 4-aminobenzoate anion, the plane of carboxylate group (C7/O1/O2) is skewed at an angle of 8.5 (2)° with the attached benzene ring (C1—C6). The dihedral angle between the benzene ring (C1—C6) and pyridine ring (N2/C8—C12) is 66.69 (8)°.

Supramolecular features top

In the crystal, the medium-strength N—H···O and O—H···O hydrogen bonds connect the adjacent anions and cations, involving water molecules into three dimensional framework (Table 2 & Fig. 2). The crystal structure also features weak C—H···π (Table 2) interactions.

Synthesis and crystallization top

4-Dimethylaminopyridine (C₇H₁₀N₂, 1.9704 g) and 4-aminobenzoic acid (C₇H₇NO₂, 2.2119 g) were taken in the equimolar ratio and synthesized in distilled water and prepared solution was allowed for slow evaporation at room temperature. Colourless blocks were collected after 20 days.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The C-bound H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 and 0.97 Å for CH_aromatic and CH₃, respectively, with U_iso(H) = 1.2Ueq(C) or 1.5Ueq(C). The H atoms bound to O and N atoms were found in a difference map and refined isotropically, with U_iso(H) = 1.5Ueq(O). The distance restraints O—H = 0.82 (1)Å and N—H = 0.88 (1)Å were applied during refinement.

Related literature top

For related structures, see: Dhanabalan et al. (2014); Lo & Ng (2008); Pereira Silva et al. (2010); Sivakumar et al. (2014).

Structure description top

We hereby report the synthesis and crystal structure of the title compound (I), prepared by the reaction of 4-dimethylaminopyridine with 4-aminobenzoic acid in distilled water as solvent.

For related structures, see: Dhanabalan et al. (2014); Lo & Ng (2008); Pereira Silva et al. (2010); Sivakumar et al. (2014).

Synthesis and crystallization top

Refinement details top

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 (I), with 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down a axis. Intermolecular Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

4-(Dimethylamino)pyridinium 4-aminobenzoate dihydrate top

Crystal data top

C₇H₁₁N₂⁺·C₇H₆NO₂⁻·2H₂O	Z = 2
M_r = 295.34	F(000) = 316
Triclinic, P1	D_x = 1.238 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3402 (7) Å	Cell parameters from 1058 reflections
b = 9.7999 (7) Å	θ = 2.3–26.7°
c = 10.2132 (8) Å	µ = 0.09 mm⁻¹
α = 65.755 (3)°	T = 295 K
β = 69.983 (2)°	Block, colourless
γ = 89.212 (3)°	0.30 × 0.24 × 0.20 mm
V = 792.08 (10) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	3337 independent reflections
Radiation source: fine-focus sealed tube	2141 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and φ scan	θ_max = 26.7°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.973, T_max = 0.982	k = −12→12
16983 measured reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0709P)² + 0.2681P] where P = (F_o² + 2F_c²)/3
3337 reflections	(Δ/σ)_max < 0.001
216 parameters	Δρ_max = 0.29 e Å⁻³
7 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₇H₁₁N₂⁺·C₇H₆NO₂⁻·2H₂O	γ = 89.212 (3)°
M_r = 295.34	V = 792.08 (10) Å³
Triclinic, P1	Z = 2
a = 9.3402 (7) Å	Mo Kα radiation
b = 9.7999 (7) Å	µ = 0.09 mm⁻¹
c = 10.2132 (8) Å	T = 295 K
α = 65.755 (3)°	0.30 × 0.24 × 0.20 mm
β = 69.983 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3337 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2141 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.982	R_int = 0.025
16983 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	7 restraints
wR(F²) = 0.168	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.29 e Å⁻³
3337 reflections	Δρ_min = −0.23 e Å⁻³
216 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.

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 > 2sigma(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	0.2531 (2)	0.4227 (2)	0.2980 (2)	0.0514 (5)
C2	0.3081 (2)	0.4846 (2)	0.1370 (2)	0.0542 (5)
H2	0.3434	0.4230	0.0871	0.065*
C3	0.3104 (2)	0.6362 (2)	0.0517 (2)	0.0531 (5)
H3	0.3492	0.6757	−0.0556	0.064*
C4	0.2567 (2)	0.7315 (2)	0.1210 (2)	0.0491 (4)
C5	0.2008 (2)	0.6690 (2)	0.2806 (2)	0.0568 (5)
H5	0.1630	0.7305	0.3302	0.068*
C6	0.1998 (2)	0.5183 (2)	0.3680 (2)	0.0581 (5)
H6	0.1631	0.4799	0.4751	0.070*
C7	0.2563 (2)	0.8938 (2)	0.0265 (3)	0.0577 (5)
C8	0.1012 (3)	0.3280 (2)	0.9041 (3)	0.0708 (6)
H8	0.0065	0.2666	0.9669	0.085*
C9	0.1039 (3)	0.4747 (2)	0.8167 (3)	0.0655 (6)
H9	0.0118	0.5130	0.8197	0.079*
C10	0.2434 (3)	0.5707 (2)	0.7214 (3)	0.0622 (6)
C11	0.3751 (3)	0.5037 (3)	0.7234 (3)	0.0903 (9)
H11	0.4716	0.5621	0.6622	0.108*
C12	0.3649 (3)	0.3550 (3)	0.8129 (3)	0.0892 (8)
H12	0.4546	0.3123	0.8114	0.107*
C13	0.3933 (4)	0.8197 (4)	0.5480 (5)	0.159 (2)
H13A	0.4464	0.8139	0.6153	0.238*
H13B	0.3738	0.9215	0.5003	0.238*
H13C	0.4557	0.7910	0.4695	0.238*
C14	0.1109 (4)	0.7869 (3)	0.6311 (4)	0.1021 (10)
H14A	0.0473	0.7295	0.6093	0.153*
H14B	0.1394	0.8888	0.5515	0.153*
H14C	0.0548	0.7877	0.7290	0.153*
N1	0.2553 (2)	0.2736 (2)	0.3824 (2)	0.0707 (5)
H1A	0.218 (3)	0.236 (3)	0.4832 (12)	0.078 (8)*
H1B	0.282 (3)	0.218 (3)	0.331 (3)	0.082 (8)*
N2	0.2282 (2)	0.2677 (2)	0.9039 (2)	0.0694 (5)
H2A	0.218 (3)	0.1687 (12)	0.961 (2)	0.079 (7)*
N3	0.2487 (3)	0.7185 (2)	0.6365 (3)	0.0864 (7)
O1	0.18777 (18)	0.97118 (16)	0.09587 (19)	0.0718 (5)
O2	0.3219 (2)	0.94822 (18)	−0.1168 (2)	0.0820 (5)
O3	0.8669 (2)	0.9002 (3)	0.2848 (2)	0.0923 (6)
H3A	0.816 (4)	0.948 (4)	0.233 (4)	0.138*
H3B	0.9578 (17)	0.921 (4)	0.225 (4)	0.138*
O4	0.6374 (2)	0.9148 (2)	0.7810 (3)	0.0908 (6)
H4A	0.5475 (17)	0.930 (4)	0.810 (4)	0.136*
H4B	0.693 (4)	0.960 (4)	0.803 (4)	0.136*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0425 (10)	0.0498 (10)	0.0531 (11)	0.0097 (8)	−0.0151 (8)	−0.0161 (9)
C2	0.0508 (11)	0.0528 (11)	0.0534 (11)	0.0106 (8)	−0.0121 (9)	−0.0236 (9)
C3	0.0493 (11)	0.0562 (11)	0.0442 (10)	0.0081 (8)	−0.0124 (8)	−0.0168 (9)
C4	0.0419 (10)	0.0491 (10)	0.0529 (11)	0.0087 (8)	−0.0171 (8)	−0.0194 (9)
C5	0.0549 (11)	0.0607 (12)	0.0589 (12)	0.0174 (9)	−0.0196 (9)	−0.0310 (10)
C6	0.0560 (12)	0.0667 (13)	0.0444 (11)	0.0145 (9)	−0.0153 (9)	−0.0202 (9)
C7	0.0482 (11)	0.0525 (11)	0.0687 (14)	0.0109 (9)	−0.0246 (10)	−0.0206 (10)
C8	0.0618 (13)	0.0555 (12)	0.0919 (17)	0.0015 (10)	−0.0354 (12)	−0.0230 (12)
C9	0.0616 (13)	0.0575 (12)	0.0797 (15)	0.0095 (10)	−0.0316 (11)	−0.0273 (11)
C10	0.0718 (14)	0.0553 (12)	0.0667 (13)	0.0014 (10)	−0.0410 (11)	−0.0202 (10)
C11	0.0593 (14)	0.0892 (18)	0.0937 (19)	−0.0039 (13)	−0.0376 (14)	−0.0048 (15)
C12	0.0643 (15)	0.0915 (19)	0.103 (2)	0.0203 (14)	−0.0437 (15)	−0.0234 (16)
C13	0.131 (3)	0.092 (2)	0.177 (4)	−0.044 (2)	−0.096 (3)	0.046 (2)
C14	0.130 (3)	0.0622 (15)	0.120 (3)	0.0295 (16)	−0.064 (2)	−0.0303 (16)
N1	0.0811 (13)	0.0549 (11)	0.0565 (12)	0.0159 (9)	−0.0167 (10)	−0.0130 (9)
N2	0.0796 (14)	0.0520 (10)	0.0877 (14)	0.0123 (10)	−0.0473 (11)	−0.0274 (10)
N3	0.0961 (16)	0.0599 (12)	0.0969 (16)	−0.0098 (11)	−0.0602 (13)	−0.0074 (11)
O1	0.0744 (10)	0.0538 (8)	0.0866 (11)	0.0189 (7)	−0.0286 (9)	−0.0308 (8)
O2	0.0879 (12)	0.0644 (10)	0.0658 (11)	0.0250 (8)	−0.0198 (9)	−0.0095 (8)
O3	0.0898 (13)	0.1101 (15)	0.0598 (11)	0.0207 (12)	−0.0261 (9)	−0.0222 (10)
O4	0.0835 (13)	0.1013 (14)	0.1038 (14)	0.0223 (11)	−0.0322 (12)	−0.0615 (12)

Geometric parameters (Å, º) top

C1—N1	1.362 (3)	C10—C11	1.389 (3)
C1—C6	1.389 (3)	C11—C12	1.348 (4)
C1—C2	1.395 (3)	C11—H11	0.9300
C2—C3	1.375 (3)	C12—N2	1.338 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.383 (3)	C13—N3	1.446 (4)
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.383 (3)	C13—H13B	0.9600
C4—C7	1.484 (3)	C13—H13C	0.9600
C5—C6	1.375 (3)	C14—N3	1.451 (4)
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—O2	1.248 (3)	C14—H14C	0.9600
C7—O1	1.267 (3)	N1—H1A	0.874 (10)
C8—N2	1.318 (3)	N1—H1B	0.885 (10)
C8—C9	1.341 (3)	N2—H2A	0.890 (10)
C8—H8	0.9300	O3—H3A	0.826 (10)
C9—C10	1.394 (3)	O3—H3B	0.825 (10)
C9—H9	0.9300	O4—H4A	0.823 (10)
C10—N3	1.339 (3)	O4—H4B	0.821 (10)

N1—C1—C6	121.60 (19)	C12—C11—C10	120.8 (2)
N1—C1—C2	120.45 (18)	C12—C11—H11	119.6
C6—C1—C2	117.94 (17)	C10—C11—H11	119.6
C3—C2—C1	120.44 (18)	N2—C12—C11	121.3 (2)
C3—C2—H2	119.8	N2—C12—H12	119.3
C1—C2—H2	119.8	C11—C12—H12	119.3
C2—C3—C4	121.77 (18)	N3—C13—H13A	109.5
C2—C3—H3	119.1	N3—C13—H13B	109.5
C4—C3—H3	119.1	H13A—C13—H13B	109.5
C3—C4—C5	117.50 (17)	N3—C13—H13C	109.5
C3—C4—C7	120.77 (18)	H13A—C13—H13C	109.5
C5—C4—C7	121.72 (18)	H13B—C13—H13C	109.5
C6—C5—C4	121.59 (19)	N3—C14—H14A	109.5
C6—C5—H5	119.2	N3—C14—H14B	109.5
C4—C5—H5	119.2	H14A—C14—H14B	109.5
C5—C6—C1	120.75 (18)	N3—C14—H14C	109.5
C5—C6—H6	119.6	H14A—C14—H14C	109.5
C1—C6—H6	119.6	H14B—C14—H14C	109.5
O2—C7—O1	122.73 (19)	C1—N1—H1A	119.5 (17)
O2—C7—C4	119.24 (19)	C1—N1—H1B	116.5 (17)
O1—C7—C4	118.02 (19)	H1A—N1—H1B	123 (2)
N2—C8—C9	122.2 (2)	C8—N2—C12	119.2 (2)
N2—C8—H8	118.9	C8—N2—H2A	117.7 (16)
C9—C8—H8	118.9	C12—N2—H2A	123.0 (16)
C8—C9—C10	120.7 (2)	C10—N3—C13	121.4 (2)
C8—C9—H9	119.7	C10—N3—C14	122.4 (2)
C10—C9—H9	119.7	C13—N3—C14	116.2 (2)
N3—C10—C11	122.6 (2)	H3A—O3—H3B	107 (4)
N3—C10—C9	121.7 (2)	H4A—O4—H4B	112 (4)
C11—C10—C9	115.7 (2)

N1—C1—C2—C3	−177.90 (19)	C5—C4—C7—O1	−7.6 (3)
C6—C1—C2—C3	0.7 (3)	N2—C8—C9—C10	−0.3 (4)
C1—C2—C3—C4	−1.1 (3)	C8—C9—C10—N3	−178.1 (2)
C2—C3—C4—C5	0.4 (3)	C8—C9—C10—C11	0.5 (4)
C2—C3—C4—C7	−178.23 (18)	N3—C10—C11—C12	178.6 (3)
C3—C4—C5—C6	0.7 (3)	C9—C10—C11—C12	0.1 (4)
C7—C4—C5—C6	179.30 (18)	C10—C11—C12—N2	−0.8 (5)
C4—C5—C6—C1	−1.1 (3)	C9—C8—N2—C12	−0.5 (4)
N1—C1—C6—C5	178.9 (2)	C11—C12—N2—C8	1.0 (4)
C2—C1—C6—C5	0.4 (3)	C11—C10—N3—C13	−3.7 (4)
C3—C4—C7—O2	−8.6 (3)	C9—C10—N3—C13	174.7 (3)
C5—C4—C7—O2	172.8 (2)	C11—C10—N3—C14	178.0 (3)
C3—C4—C7—O1	171.01 (18)	C9—C10—N3—C14	−3.5 (4)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.87 (1)	2.04 (1)	2.898 (3)	167 (2)
N1—H1B···O4ⁱ	0.89 (1)	2.04 (1)	2.921 (3)	174 (2)
N2—H2A···O1ⁱⁱ	0.89 (1)	1.81 (1)	2.697 (2)	174 (2)
O3—H3A···O2ⁱⁱⁱ	0.83 (1)	2.03 (1)	2.858 (3)	175 (4)
O3—H3B···O1^iv	0.83 (1)	2.04 (1)	2.861 (3)	174 (4)
O4—H4A···O2^v	0.82 (1)	2.01 (1)	2.834 (3)	175 (4)
O4—H4B···O1^vi	0.82 (1)	2.04 (1)	2.847 (3)	167 (4)
C9—H9···Cg2^vii	0.93	2.80	3.510 (3)	134
C12—H12···Cg2ⁱ	0.93	2.84	3.535 (3)	132

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

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.874 (10)	2.042 (12)	2.898 (3)	167 (2)
N1—H1B···O4ⁱ	0.885 (10)	2.039 (11)	2.921 (3)	174 (2)
N2—H2A···O1ⁱⁱ	0.890 (10)	1.811 (10)	2.697 (2)	174 (2)
O3—H3A···O2ⁱⁱⁱ	0.826 (10)	2.034 (11)	2.858 (3)	175 (4)
O3—H3B···O1^iv	0.825 (10)	2.039 (11)	2.861 (3)	174 (4)
O4—H4A···O2^v	0.823 (10)	2.013 (11)	2.834 (3)	175 (4)
O4—H4B···O1^vi	0.821 (10)	2.042 (14)	2.847 (3)	167 (4)
C9—H9···Cg2^vii	0.93	2.80	3.510 (3)	134
C12—H12···Cg2ⁱ	0.93	2.84	3.535 (3)	132

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

Acknowledgements

The authors thank SAIF, IIT, Madras for thedata collection.

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Volume 71| Part 1| January 2015| Pages o26-o27

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