1-(5-Amino-2,4-dinitro­phen­yl)pyridinium chloride monohydrate

Babykala, R.; Kalaivani, D.

doi:10.1107/S1600536812038834

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2941

https://doi.org/10.1107/S1600536812038834

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1-(5-Amino-2,4-dinitrophenyl)pyridinium chloride monohydrate

Rajamanickam Babykala ^a and Doraisamyraja Kalaivani ^a ^*

^aPG and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli 620 002, Tamil Nadu, India
^*Correspondence e-mail: kalaivbalaj@yahoo.co.in

(Received 7 July 2012; accepted 10 September 2012; online 15 September 2012)

In the cation of the title hydrated salt, C₁₁H₉N₄O₄⁺·Cl⁻·H₂O, the six-membered rings are inclined to each other at 79.0 (1)° and an intramolecular N—H⋯O hydrogen bond occurs. In the crystal, N—H⋯Cl hydrogen bonds link two cations and two anions into centrosymmetric group, and O—H⋯Cl hydrogen bonds involving the water molecules further link these groups into chains in [101]. An O—H⋯O interaction is also present. The water molecule is disordered over two sets of sites in a 0.555 (13):0.445 (13) ratio

Related literature

For applications of N-substituted pyridinium salts, see: Sliwa (1996 ); Ali et al. (2005 ); Chelossi et al. (2006 ); Azzouz et al. (2008 ). For related structures, see: Shmidt et al. (2005 ); Wojtas et al. (2006 ); Manickkam & Kalaivani (2011 ); Chernyshev et al. (2011 ); Sridevi & Kalaivani (2012 ).

Experimental

Crystal data

C₁₁H₉N₄O₄⁺·Cl⁻·H₂O
M_r = 314.69
Monoclinic, P 2₁ /c
a = 5.4312 (4) Å
b = 21.493 (2) Å
c = 11.3892 (9) Å
β = 92.362 (3)°
V = 1328.33 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.871, T_max = 0.939
14754 measured reflections
3125 independent reflections
2288 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.112
S = 1.03
3125 reflections
224 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O4	0.86 (2)	2.09 (2)	2.671 (2)	124 (2)
N4—H4B⋯Cl1	0.87 (2)	2.35 (2)	3.2162 (19)	171 (2)
N4—H4A⋯Cl1ⁱ	0.86 (2)	2.56 (2)	3.2268 (16)	135 (2)
O5—H5B⋯Cl1	0.90 (2)	2.34 (3)	3.187 (3)	158 (5)
O5—H5A⋯Cl1ⁱⁱ	0.93 (2)	2.51 (2)	3.429 (9)	169 (5)
O5′—H5D⋯O5ⁱⁱⁱ	0.91 (2)	1.94 (3)	2.815 (16)	160 (5)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x-1, y, z; (iii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812038834/cv5319sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038834/cv5319Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812038834/cv5319Isup3.cml

checkCIF report

Comment top

N-Substitued pyridinium salts are widely used in organic synthesis (Azzouz et al., 2008), medicinal field (Chelossi et al., 2006), electrodeposition (Ali et al., 2005) and dye preparations (Sliwa, 1996). As a continuation of our studies of new substituted pyridinium barbiturates (Manickkam & Kalaivani, 2011; Sridevi & Kalaivani, 2012), we report the crystal structure of the title compound, (I).

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related compounds (Shmidt et al., 2005; Wojtas et al., 2006; Chernyshev et al., 2011). In the cation, the pyridine ring is twisted notably from the dinitrophenyl ring and the dihedral angle between their planes is 78.93 (5)°. The two nitro groups, O1—N2—O2 and O3—N3—O4, deviate from the benzene ring at 7.97 (10)° and 4.18 (17)°, respectively. Intermolecular N—H···Cl and O—H···Cl hydrogen bonds (Table 1) consolidate the crystal packing. The overall molecular packing forming a herring bone arrangement when view down c axis is shown in Fig. 2.

Related literature top

For applications of N-substituted pyridinium salts, see: Sliwa (1996); Ali et al. (2005); Chelossi et al. (2006); Azzouz et al. (2008). For related structures, see: Shmidt et al. (2005); Wojtas et al. (2006); Manickkam & Kalaivani (2011); Chernyshev et al. (2011); Sridevi & Kalaivani (2012).

Experimental top

Analytical grade 1,3-dichloro-4,6-dinitrobenzene (DCDNB) and barbituric acid were used as supplied by Aldrich company. Pyridine was distilled under reduced pressure and the fraction boiling over at its boiling point was used for the preparation of the title molecular salt.DCDNB (2.01 g, 0.01 mol) in 15 ml absolute ethanol was mixed with barbituric acid (1.28 g, 0.01 mol) in 30 ml of absolute ethanol. Pyridine (3.16 g, 0.04 mol)was added to the above mixture which was heated to 40°C and shaken well for 5–6 hrs. The solution was kept as such at room temperature for 48 hrs. On standing dark violet colour crystals separate out.After filtering out these violet crystals, the filterate was kept as such at room temperature (25°C).From the filtrate, one of the by-products of the reaction between DCDNB, barbituric acid and pyridine, separates as pale greenish yellow crystals after 3 months. These crystals were powdered well, and washed with copious amount of ethanol and dry ether, recrystallized from absolute alcohol and subjected to single-crystal X-ray analysis. Yield: 40–50%; m.p.: 508 K.

Structure description top

For applications of N-substituted pyridinium salts, see: Sliwa (1996); Ali et al. (2005); Chelossi et al. (2006); Azzouz et al. (2008). For related structures, see: Shmidt et al. (2005); Wojtas et al. (2006); Manickkam & Kalaivani (2011); Chernyshev et al. (2011); Sridevi & Kalaivani (2012).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The content of asymmetric unit of the title compound showing the atomic labelling and 40% probability displacement ellipsoids. Dashed lines denote hydrogen bonds. Only major component of the disordered water molecule is shown.
	Fig. 2. A portion of the crystal packing viewed down the c axis and showing the herring bone arrangement of the molecules. Only major components of the disordered water molecules are shown. H atoms were omitted for clarity.

1-(5-Amino-2,4-dinitrophenyl)pyridinium chloride monohydrate top

Crystal data top

C₁₁H₉N₄O₄⁺·Cl⁻·H₂O	F(000) = 648
M_r = 314.69	D_x = 1.574 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4581 reflections
a = 5.4312 (4) Å	θ = 2.6–25.4°
b = 21.493 (2) Å	µ = 0.32 mm⁻¹
c = 11.3892 (9) Å	T = 293 K
β = 92.362 (3)°	Block, red
V = 1328.33 (19) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3125 independent reflections
Radiation source: fine-focus sealed tube	2288 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and φ scan	θ_max = 27.9°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→6
T_min = 0.871, T_max = 0.939	k = −28→28
14754 measured reflections	l = −11→14

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0538P)² + 0.2604P] where P = (F_o² + 2F_c²)/3
3125 reflections	(Δ/σ)_max = 0.001
224 parameters	Δρ_max = 0.20 e Å⁻³
9 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₁H₉N₄O₄⁺·Cl⁻·H₂O	V = 1328.33 (19) Å³
M_r = 314.69	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.4312 (4) Å	µ = 0.32 mm⁻¹
b = 21.493 (2) Å	T = 293 K
c = 11.3892 (9) Å	0.30 × 0.25 × 0.20 mm
β = 92.362 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3125 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2288 reflections with I > 2σ(I)
T_min = 0.871, T_max = 0.939	R_int = 0.031
14754 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	9 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.20 e Å⁻³
3125 reflections	Δρ_min = −0.27 e Å⁻³
224 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.

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 > σ(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	Occ. (<1)
C1	0.3483 (3)	0.66419 (8)	0.10183 (14)	0.0449 (4)
H1	0.4780	0.6878	0.1336	0.054*
C2	0.3105 (3)	0.66065 (9)	−0.01760 (15)	0.0531 (4)
H2	0.4149	0.6814	−0.0671	0.064*
C3	0.1174 (4)	0.62626 (9)	−0.06342 (15)	0.0563 (5)
H3	0.0871	0.6242	−0.1443	0.068*
C4	−0.0302 (4)	0.59508 (11)	0.01082 (17)	0.0663 (6)
H4	−0.1607	0.5712	−0.0194	0.080*
C5	0.0137 (3)	0.59893 (10)	0.12967 (16)	0.0613 (5)
H5	−0.0855	0.5773	0.1803	0.074*
C6	0.2469 (3)	0.63860 (8)	0.29921 (13)	0.0403 (4)
C7	0.1136 (3)	0.67842 (8)	0.37070 (14)	0.0414 (4)
C8	0.1804 (3)	0.68200 (8)	0.48832 (14)	0.0441 (4)
H8	0.0915	0.7076	0.5370	0.053*
C9	0.3760 (3)	0.64842 (8)	0.53520 (13)	0.0432 (4)
C10	0.5080 (3)	0.60594 (8)	0.46686 (13)	0.0439 (4)
C11	0.4326 (3)	0.60318 (8)	0.34576 (14)	0.0446 (4)
H11	0.5138	0.5761	0.2969	0.054*
N2	−0.0913 (3)	0.71602 (7)	0.32853 (13)	0.0493 (4)
N1	0.1997 (2)	0.63388 (6)	0.17294 (11)	0.0404 (3)
N3	0.4403 (3)	0.65911 (7)	0.65862 (12)	0.0517 (4)
O1	−0.1404 (2)	0.71820 (7)	0.22235 (12)	0.0628 (4)
O2	−0.2092 (3)	0.74376 (8)	0.40064 (13)	0.0787 (5)
O3	0.3182 (3)	0.69609 (7)	0.71230 (11)	0.0676 (4)
O4	0.6154 (3)	0.63139 (8)	0.70329 (11)	0.0740 (4)
N4	0.6928 (3)	0.57003 (8)	0.50422 (14)	0.0560 (4)
O5	0.3996 (12)	0.4960 (2)	0.1460 (6)	0.0653 (17)	0.555 (13)
O5'	0.4978 (12)	0.5075 (2)	0.0942 (7)	0.0622 (16)	0.445 (13)
Cl1	0.88637 (9)	0.47657 (2)	0.30769 (4)	0.06455 (18)
H5A	0.274 (7)	0.487 (3)	0.196 (5)	0.15 (2)*	0.555 (13)
H5B	0.556 (4)	0.494 (4)	0.174 (5)	0.15 (2)*	0.555 (13)
H5C	0.520 (14)	0.481 (3)	0.156 (4)	0.08 (3)*	0.445 (13)
H5D	0.554 (9)	0.499 (3)	0.022 (2)	0.064 (16)*	0.445 (13)
H4A	0.747 (3)	0.5711 (10)	0.5766 (14)	0.063 (6)*
H4B	0.759 (4)	0.5437 (9)	0.4563 (18)	0.071 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0445 (9)	0.0485 (9)	0.0413 (8)	−0.0051 (7)	−0.0018 (7)	0.0032 (7)
C2	0.0619 (11)	0.0584 (11)	0.0389 (9)	−0.0033 (8)	0.0029 (8)	0.0053 (8)
C3	0.0658 (12)	0.0667 (12)	0.0356 (8)	0.0059 (9)	−0.0056 (8)	0.0004 (8)
C4	0.0556 (11)	0.0906 (15)	0.0512 (11)	−0.0181 (10)	−0.0147 (9)	−0.0037 (10)
C5	0.0503 (10)	0.0871 (15)	0.0460 (9)	−0.0243 (10)	−0.0043 (8)	0.0058 (9)
C6	0.0384 (8)	0.0504 (9)	0.0318 (7)	−0.0074 (7)	−0.0034 (6)	0.0046 (6)
C7	0.0376 (8)	0.0440 (9)	0.0423 (8)	−0.0045 (6)	−0.0038 (6)	0.0045 (7)
C8	0.0464 (9)	0.0448 (9)	0.0412 (8)	−0.0039 (7)	0.0016 (7)	0.0002 (7)
C9	0.0481 (9)	0.0496 (9)	0.0315 (7)	−0.0067 (7)	−0.0022 (6)	0.0051 (7)
C10	0.0417 (8)	0.0514 (9)	0.0380 (8)	−0.0035 (7)	−0.0038 (7)	0.0073 (7)
C11	0.0418 (8)	0.0567 (10)	0.0353 (8)	0.0023 (7)	−0.0001 (6)	0.0029 (7)
N2	0.0442 (8)	0.0472 (8)	0.0556 (9)	−0.0020 (6)	−0.0096 (7)	0.0005 (7)
N1	0.0377 (6)	0.0501 (8)	0.0328 (6)	−0.0028 (6)	−0.0047 (5)	0.0041 (5)
N3	0.0631 (9)	0.0549 (9)	0.0365 (7)	−0.0051 (7)	−0.0052 (7)	0.0035 (7)
O1	0.0581 (8)	0.0727 (9)	0.0557 (8)	0.0073 (6)	−0.0222 (6)	−0.0006 (7)
O2	0.0757 (10)	0.0902 (11)	0.0696 (9)	0.0342 (8)	−0.0052 (8)	−0.0106 (8)
O3	0.0897 (10)	0.0747 (9)	0.0384 (7)	0.0102 (8)	0.0017 (7)	−0.0052 (6)
O4	0.0846 (10)	0.0864 (11)	0.0486 (8)	0.0167 (8)	−0.0252 (7)	−0.0053 (7)
N4	0.0577 (9)	0.0683 (11)	0.0409 (8)	0.0125 (8)	−0.0111 (7)	0.0022 (8)
O5	0.066 (3)	0.075 (2)	0.054 (3)	0.0075 (19)	−0.014 (2)	−0.0065 (17)
O5'	0.057 (3)	0.079 (2)	0.050 (3)	0.0092 (19)	0.001 (2)	0.002 (2)
Cl1	0.0775 (3)	0.0563 (3)	0.0576 (3)	0.0081 (2)	−0.0250 (2)	0.0010 (2)

Geometric parameters (Å, º) top

C1—N1	1.336 (2)	C8—H8	0.9300
C1—C2	1.369 (2)	C9—C10	1.414 (2)
C1—H1	0.9300	C9—N3	1.4528 (19)
C2—C3	1.369 (3)	C10—N4	1.323 (2)
C2—H2	0.9300	C10—C11	1.424 (2)
C3—C4	1.365 (3)	C11—H11	0.9300
C3—H3	0.9300	N2—O2	1.2176 (19)
C4—C5	1.367 (3)	N2—O1	1.2285 (18)
C4—H4	0.9300	N3—O4	1.2158 (19)
C5—N1	1.336 (2)	N3—O3	1.216 (2)
C5—H5	0.9300	N4—H4A	0.864 (15)
C6—C11	1.354 (2)	N4—H4B	0.874 (16)
C6—C7	1.403 (2)	O5—H5A	0.930 (19)
C6—N1	1.4540 (19)	O5—H5B	0.90 (2)
C7—C8	1.375 (2)	O5'—H5C	0.916 (19)
C7—N2	1.442 (2)	O5'—H5D	0.913 (19)
C8—C9	1.374 (2)

N1—C1—C2	120.36 (15)	C8—C9—C10	121.78 (14)
N1—C1—H1	119.8	C8—C9—N3	116.37 (15)
C2—C1—H1	119.8	C10—C9—N3	121.85 (14)
C3—C2—C1	119.33 (16)	N4—C10—C9	126.50 (15)
C3—C2—H2	120.3	N4—C10—C11	118.14 (16)
C1—C2—H2	120.3	C9—C10—C11	115.35 (14)
C4—C3—C2	119.29 (16)	C6—C11—C10	122.40 (16)
C4—C3—H3	120.4	C6—C11—H11	118.8
C2—C3—H3	120.4	C10—C11—H11	118.8
C3—C4—C5	120.05 (18)	O2—N2—O1	123.14 (15)
C3—C4—H4	120.0	O2—N2—C7	118.02 (14)
C5—C4—H4	120.0	O1—N2—C7	118.83 (15)
N1—C5—C4	119.83 (17)	C1—N1—C5	121.11 (14)
N1—C5—H5	120.1	C1—N1—C6	118.62 (13)
C4—C5—H5	120.1	C5—N1—C6	120.26 (13)
C11—C6—C7	120.64 (14)	O4—N3—O3	122.92 (14)
C11—C6—N1	116.52 (14)	O4—N3—C9	118.69 (15)
C7—C6—N1	122.83 (14)	O3—N3—C9	118.39 (15)
C8—C7—C6	118.53 (14)	C10—N4—H4A	121.1 (14)
C8—C7—N2	117.52 (15)	C10—N4—H4B	120.2 (15)
C6—C7—N2	123.95 (14)	H4A—N4—H4B	119 (2)
C9—C8—C7	121.18 (15)	H5A—O5—H5B	119 (3)
C9—C8—H8	119.4	H5A—O5—H5C	119 (5)
C7—C8—H8	119.4	H5C—O5'—H5D	122 (4)

N1—C1—C2—C3	0.7 (3)	N4—C10—C11—C6	−179.34 (16)
C1—C2—C3—C4	−1.4 (3)	C9—C10—C11—C6	−0.2 (2)
C2—C3—C4—C5	0.7 (3)	C8—C7—N2—O2	−7.3 (2)
C3—C4—C5—N1	0.8 (3)	C6—C7—N2—O2	172.42 (16)
C11—C6—C7—C8	1.9 (2)	C8—C7—N2—O1	173.29 (15)
N1—C6—C7—C8	−176.69 (14)	C6—C7—N2—O1	−6.9 (2)
C11—C6—C7—N2	−177.90 (15)	C2—C1—N1—C5	0.9 (3)
N1—C6—C7—N2	3.5 (2)	C2—C1—N1—C6	179.68 (16)
C6—C7—C8—C9	1.2 (2)	C4—C5—N1—C1	−1.6 (3)
N2—C7—C8—C9	−178.98 (14)	C4—C5—N1—C6	179.61 (18)
C7—C8—C9—C10	−3.9 (2)	C11—C6—N1—C1	−78.17 (19)
C7—C8—C9—N3	175.86 (15)	C7—C6—N1—C1	100.44 (18)
C8—C9—C10—N4	−177.62 (17)	C11—C6—N1—C5	100.64 (19)
N3—C9—C10—N4	2.6 (3)	C7—C6—N1—C5	−80.8 (2)
C8—C9—C10—C11	3.3 (2)	C8—C9—N3—O4	−178.50 (16)
N3—C9—C10—C11	−176.45 (14)	C10—C9—N3—O4	1.3 (2)
C7—C6—C11—C10	−2.4 (2)	C8—C9—N3—O3	0.6 (2)
N1—C6—C11—C10	176.28 (14)	C10—C9—N3—O3	−179.63 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O4	0.86 (2)	2.09 (2)	2.671 (2)	124 (2)
N4—H4B···Cl1	0.87 (2)	2.35 (2)	3.2162 (19)	171 (2)
N4—H4A···Cl1ⁱ	0.86 (2)	2.56 (2)	3.2268 (16)	135 (2)
O5—H5B···Cl1	0.90 (2)	2.34 (3)	3.187 (3)	158 (5)
O5—H5A···Cl1ⁱⁱ	0.93 (2)	2.51 (2)	3.429 (9)	169 (5)
O5′—H5D···O5ⁱⁱⁱ	0.91 (2)	1.94 (3)	2.815 (16)	160 (5)

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

Experimental details

Crystal data
Chemical formula	C₁₁H₉N₄O₄⁺·Cl⁻·H₂O
M_r	314.69
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	5.4312 (4), 21.493 (2), 11.3892 (9)
β (°)	92.362 (3)
V (Å³)	1328.33 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.871, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	14754, 3125, 2288
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.112, 1.03
No. of reflections	3125
No. of parameters	224
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.27

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O4	0.864 (15)	2.088 (19)	2.671 (2)	124.3 (17)
N4—H4B···Cl1	0.874 (16)	2.349 (17)	3.2162 (19)	171 (2)
N4—H4A···Cl1ⁱ	0.864 (15)	2.556 (18)	3.2268 (16)	135.2 (17)
O5—H5B···Cl1	0.90 (2)	2.34 (3)	3.187 (3)	158 (5)
O5—H5A···Cl1ⁱⁱ	0.930 (19)	2.51 (2)	3.429 (9)	169 (5)
O5'—H5D···O5ⁱⁱⁱ	0.913 (19)	1.94 (3)	2.815 (16)	160 (5)

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

Acknowledgements

The authors are thankful to SAIF, IIT Madras, for the data collection.

References

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