4-Hy­droxy-2-methyl-1,1-dioxo-N-phenyl-2H-1λ6,2-benzothia­zine-3-carboxamide

Aman, F.; Siddiqui, W.A.; Ashraf, A.; Siddiqui, H.L.; Parvez, M.

doi:10.1107/S1600536812021708

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1790

doi:10.1107/S1600536812021708

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4-Hydroxy-2-methyl-1,1-dioxo-N-phenyl-2H-1λ⁶,2-benzothiazine-3-carboxamide

Farhana Aman,^a Waseeq Ahmad Siddiqui,^a ^* Adnan Ashraf,^a Hamid Latif Siddiqui ^b and Masood Parvez ^c

^aDepartment of Chemistry, University of Sargodha, Sargodha 40100, Pakistan, ^bInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, and ^cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: waseeq786@gmail.com

(Received 10 May 2012; accepted 14 May 2012; online 19 May 2012)

In the title molecule, C₁₆H₁₄N₂O₄S, the thiazine ring adopts a twist chair conformation with the N and adjacent C atom displaced by 0.966 (3) and 0.386 (4) Å, respectively, on the same side of the mean plane formed by the remaining ring atoms. The dihedral angle between the mean planes of the benzene rings is 37.65 (10)°. The molecular structure features an intramolecular O—H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For background to the biological activity of benzothiazine derivatives, and further synthetic details, see: Siddiqui et al. (2007 ); Ahmad et al. (2010 ). For related structures, see: Siddiqui et al. (2008 ; 2009 ).

Experimental

Crystal data

C₁₆H₁₄N₂O₄S
M_r = 330.35
Monoclinic, P 2₁ /c
a = 10.502 (2) Å
b = 7.649 (3) Å
c = 19.235 (4) Å
β = 103.395 (15)°
V = 1503.1 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.10 × 0.08 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.977, T_max = 0.984
12580 measured reflections
3450 independent reflections
2901 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.119
S = 1.06
3450 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1ⁱ	0.88	2.26	2.987 (2)	140
C3—H3⋯O2ⁱⁱ	0.95	2.48	3.300 (3)	145
C13—H13⋯O4ⁱⁱⁱ	0.95	2.48	3.339 (3)	151
O3—H3O⋯O4	0.84	1.79	2.534 (2)	146
Symmetry codes: (i) -x, -y+1, -z; (ii) $[-x, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812021708/hb6789sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021708/hb6789Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021708/hb6789Isup3.cml

checkCIF report

Comment top

In continuation of our research on the synthesis of potentially biologically active 1,2-benzothiazine 1,1-dioxide derivatives (Siddiqui et al., 2007; Ahmad et al., 2010) herein, we report the synthesis and crystal structure of the title compound.

The bond distances and angles in the title compound (Fig. 1) agree very well with the corresponding bond distances and angles reported in closely related compounds (Siddiqui et al., 2008; 2009). The heterocyclic thiazine ring adopts a twist chair conformation with atoms S1 and C1 displaced by 0.966 (3) and 0.386 (4) Å, respectively, on the same side from the mean plane formed by the remaining ring atoms (r.m.s. deviation 0.004 for N1/C6–C8 atoms). The mean-plane of the benzene rings C1–C6 and C11–C16 are inclined at a dihedral angle 37.65 (10)° with respect to each other.

The molecular structure is stabilized by an intra-molecular O3—H3O···O4 hydrogen bond. The crystal packing is consolidated by intermolecular N2—H2N···O1, C3—H3···O2 and C13—H13···O4 hydrogen bonds (Fig. 2 and Table 1).

Related literature top

For background to the biological activity of benzothiazine derivatives, and further synthetic details, see: Siddiqui et al. (2007); Ahmad et al. (2010). For related structures, see: Siddiqui et al. (2008; 2009).

Experimental top

A mixture of 4-hydroxy-2-methyl-2H-1,2 benzothiazine-3-carboxylic acid methyl ester 1,1 dioxide (0.65 g, 2.42 mmol) and aniline (0.65 ml, 2.42 mmol) in xylene (150 ml) was allowed to react as per reported procedure (Siddiqui et al., 2007) to isolate the title compound. Colourless prisms were grown from ethyl acetate solution by slow evaporation at room temperature; m.p. = 484–485 K

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A part of the unit cell showing hydrogen bonding interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity.

4-Hydroxy-2-methyl-1,1-dioxo-N-phenyl-2H- 1λ⁶,2-benzothiazine-3-carboxamide top

Crystal data top

C₁₆H₁₄N₂O₄S	F(000) = 688
M_r = 330.35	D_x = 1.460 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6808 reflections
a = 10.502 (2) Å	θ = 1.0–27.5°
b = 7.649 (3) Å	µ = 0.24 mm⁻¹
c = 19.235 (4) Å	T = 173 K
β = 103.395 (15)°	Prism, colorless
V = 1503.1 (7) Å³	0.10 × 0.08 × 0.07 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	3450 independent reflections
Radiation source: fine-focus sealed tube	2901 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ω and ϕ scans	θ_max = 27.6°, θ_min = 2.0°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −13→13
T_min = 0.977, T_max = 0.984	k = −9→9
12580 measured reflections	l = −24→24

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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F²) = 0.119	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0433P)² + 1.2798P] where P = (F_o² + 2F_c²)/3
3450 reflections	(Δ/σ)_max = 0.002
210 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₆H₁₄N₂O₄S	V = 1503.1 (7) Å³
M_r = 330.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.502 (2) Å	µ = 0.24 mm⁻¹
b = 7.649 (3) Å	T = 173 K
c = 19.235 (4) Å	0.10 × 0.08 × 0.07 mm
β = 103.395 (15)°

Data collection top

Nonius KappaCCD diffractometer	3450 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	2901 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.984	R_int = 0.059
12580 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.06	Δρ_max = 0.52 e Å⁻³
3450 reflections	Δρ_min = −0.31 e Å⁻³
210 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
S1	0.06977 (5)	0.65050 (7)	−0.08374 (3)	0.02930 (15)
O1	0.03451 (13)	0.7324 (2)	−0.02412 (8)	0.0343 (4)
O2	−0.03040 (14)	0.5885 (2)	−0.14150 (8)	0.0397 (4)
O3	0.46114 (13)	0.7361 (2)	0.03008 (8)	0.0336 (3)
H3O	0.4835	0.6611	0.0625	0.050*
O4	0.44020 (13)	0.4617 (2)	0.10046 (7)	0.0327 (3)
N1	0.16698 (15)	0.4874 (2)	−0.05340 (8)	0.0269 (4)
N2	0.25707 (16)	0.2921 (2)	0.06629 (9)	0.0286 (4)
H2N	0.1836	0.2817	0.0335	0.034*
C1	0.1745 (2)	0.7916 (3)	−0.11620 (10)	0.0290 (4)
C2	0.1311 (2)	0.8897 (3)	−0.17712 (11)	0.0344 (5)
H2	0.0429	0.8807	−0.2036	0.041*
C3	0.2174 (2)	1.0016 (3)	−0.19931 (12)	0.0374 (5)
H3	0.1892	1.0690	−0.2415	0.045*
C4	0.3453 (2)	1.0147 (3)	−0.15962 (12)	0.0349 (5)
H4	0.4040	1.0927	−0.1747	0.042*
C5	0.3885 (2)	0.9167 (3)	−0.09875 (11)	0.0312 (4)
H5	0.4762	0.9286	−0.0719	0.037*
C6	0.30455 (19)	0.8003 (3)	−0.07627 (10)	0.0267 (4)
C7	0.34974 (18)	0.6857 (3)	−0.01458 (10)	0.0265 (4)
C8	0.28462 (18)	0.5399 (3)	−0.00344 (10)	0.0258 (4)
C9	0.33296 (18)	0.4289 (3)	0.05864 (10)	0.0275 (4)
C10	0.1852 (2)	0.3560 (3)	−0.10655 (12)	0.0386 (5)
H10A	0.2385	0.2592	−0.0821	0.046*
H10B	0.2296	0.4101	−0.1406	0.046*
H10C	0.0997	0.3115	−0.1322	0.046*
C11	0.28010 (19)	0.1627 (3)	0.12035 (11)	0.0293 (4)
C12	0.3610 (2)	0.1906 (3)	0.18722 (11)	0.0338 (5)
H12	0.4041	0.2997	0.1986	0.041*
C13	0.3782 (2)	0.0577 (3)	0.23736 (13)	0.0426 (6)
H13	0.4344	0.0758	0.2832	0.051*
C14	0.3156 (3)	−0.0998 (4)	0.22204 (15)	0.0486 (6)
H14	0.3279	−0.1898	0.2570	0.058*
C15	0.2342 (3)	−0.1267 (3)	0.15529 (15)	0.0497 (6)
H15	0.1904	−0.2355	0.1445	0.060*
C16	0.2163 (2)	0.0035 (3)	0.10429 (13)	0.0395 (5)
H16	0.1606	−0.0156	0.0584	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0215 (2)	0.0334 (3)	0.0307 (3)	0.0006 (2)	0.00107 (18)	−0.0006 (2)
O1	0.0239 (7)	0.0404 (9)	0.0390 (8)	0.0016 (6)	0.0082 (6)	−0.0030 (7)
O2	0.0295 (8)	0.0462 (10)	0.0373 (8)	−0.0022 (7)	−0.0046 (6)	−0.0019 (7)
O3	0.0269 (7)	0.0359 (8)	0.0334 (8)	−0.0061 (6)	−0.0021 (6)	0.0031 (6)
O4	0.0277 (7)	0.0370 (8)	0.0296 (7)	−0.0034 (6)	−0.0011 (6)	0.0033 (6)
N1	0.0228 (8)	0.0292 (9)	0.0267 (8)	−0.0014 (7)	0.0016 (6)	−0.0016 (7)
N2	0.0238 (8)	0.0316 (9)	0.0288 (8)	0.0000 (7)	0.0027 (6)	0.0034 (7)
C1	0.0293 (10)	0.0288 (11)	0.0283 (10)	0.0018 (8)	0.0052 (8)	0.0002 (8)
C2	0.0357 (11)	0.0340 (12)	0.0301 (10)	0.0059 (9)	0.0010 (8)	0.0011 (9)
C3	0.0528 (14)	0.0295 (11)	0.0295 (10)	0.0065 (10)	0.0088 (9)	0.0033 (9)
C4	0.0445 (12)	0.0261 (11)	0.0376 (11)	0.0015 (9)	0.0166 (9)	0.0016 (9)
C5	0.0310 (10)	0.0286 (10)	0.0349 (11)	0.0022 (8)	0.0093 (8)	−0.0004 (9)
C6	0.0260 (10)	0.0252 (10)	0.0287 (9)	0.0024 (8)	0.0061 (7)	−0.0014 (8)
C7	0.0205 (9)	0.0307 (10)	0.0275 (9)	0.0009 (7)	0.0040 (7)	−0.0032 (8)
C8	0.0219 (9)	0.0280 (10)	0.0260 (9)	0.0002 (7)	0.0025 (7)	−0.0001 (8)
C9	0.0239 (9)	0.0298 (10)	0.0288 (10)	0.0013 (8)	0.0062 (7)	−0.0004 (8)
C10	0.0436 (13)	0.0346 (12)	0.0344 (11)	0.0039 (10)	0.0025 (9)	−0.0071 (9)
C11	0.0256 (10)	0.0294 (10)	0.0353 (11)	0.0050 (8)	0.0117 (8)	0.0044 (9)
C12	0.0358 (11)	0.0349 (12)	0.0317 (10)	0.0027 (9)	0.0099 (8)	0.0020 (9)
C13	0.0440 (13)	0.0511 (15)	0.0342 (11)	0.0086 (11)	0.0118 (10)	0.0098 (11)
C14	0.0510 (15)	0.0430 (14)	0.0551 (15)	0.0076 (12)	0.0188 (12)	0.0207 (12)
C15	0.0505 (15)	0.0320 (13)	0.0688 (17)	−0.0029 (11)	0.0184 (13)	0.0108 (12)
C16	0.0370 (12)	0.0339 (12)	0.0468 (13)	−0.0009 (10)	0.0082 (10)	0.0036 (10)

Geometric parameters (Å, º) top

S1—O2	1.4228 (15)	C5—C6	1.390 (3)
S1—O1	1.4288 (15)	C5—H5	0.9500
S1—N1	1.6316 (18)	C6—C7	1.463 (3)
S1—C1	1.756 (2)	C7—C8	1.351 (3)
O3—C7	1.338 (2)	C8—C9	1.458 (3)
O3—H3O	0.8400	C10—H10A	0.9800
O4—C9	1.249 (2)	C10—H10B	0.9800
N1—C8	1.436 (2)	C10—H10C	0.9800
N1—C10	1.478 (3)	C11—C12	1.384 (3)
N2—C9	1.344 (3)	C11—C16	1.389 (3)
N2—C11	1.415 (3)	C12—C13	1.384 (3)
N2—H2N	0.8800	C12—H12	0.9500
C1—C2	1.377 (3)	C13—C14	1.372 (4)
C1—C6	1.405 (3)	C13—H13	0.9500
C2—C3	1.385 (3)	C14—C15	1.383 (4)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.386 (3)	C15—C16	1.380 (3)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.376 (3)	C16—H16	0.9500
C4—H4	0.9500

O2—S1—O1	119.39 (9)	O3—C7—C6	114.78 (17)
O2—S1—N1	108.21 (10)	C8—C7—C6	122.84 (18)
O1—S1—N1	107.76 (9)	C7—C8—N1	120.90 (17)
O2—S1—C1	109.76 (10)	C7—C8—C9	121.19 (18)
O1—S1—C1	108.43 (10)	N1—C8—C9	117.89 (17)
N1—S1—C1	101.85 (9)	O4—C9—N2	123.74 (19)
C7—O3—H3O	109.5	O4—C9—C8	120.11 (18)
C8—N1—C10	115.09 (16)	N2—C9—C8	116.15 (17)
C8—N1—S1	113.31 (14)	N1—C10—H10A	109.5
C10—N1—S1	116.32 (13)	N1—C10—H10B	109.5
C9—N2—C11	128.34 (17)	H10A—C10—H10B	109.5
C9—N2—H2N	115.8	N1—C10—H10C	109.5
C11—N2—H2N	115.8	H10A—C10—H10C	109.5
C2—C1—C6	121.9 (2)	H10B—C10—H10C	109.5
C2—C1—S1	121.73 (16)	C12—C11—C16	120.2 (2)
C6—C1—S1	116.40 (15)	C12—C11—N2	122.6 (2)
C1—C2—C3	119.2 (2)	C16—C11—N2	117.26 (19)
C1—C2—H2	120.4	C11—C12—C13	119.1 (2)
C3—C2—H2	120.4	C11—C12—H12	120.4
C4—C3—C2	119.7 (2)	C13—C12—H12	120.4
C4—C3—H3	120.2	C14—C13—C12	121.1 (2)
C2—C3—H3	120.2	C14—C13—H13	119.4
C5—C4—C3	121.1 (2)	C12—C13—H13	119.4
C5—C4—H4	119.5	C13—C14—C15	119.5 (2)
C3—C4—H4	119.5	C13—C14—H14	120.2
C4—C5—C6	120.4 (2)	C15—C14—H14	120.2
C4—C5—H5	119.8	C16—C15—C14	120.4 (2)
C6—C5—H5	119.8	C16—C15—H15	119.8
C5—C6—C1	117.81 (18)	C14—C15—H15	119.8
C5—C6—C7	121.73 (18)	C15—C16—C11	119.7 (2)
C1—C6—C7	120.43 (18)	C15—C16—H16	120.2
O3—C7—C8	122.38 (18)	C11—C16—H16	120.2

O2—S1—N1—C8	169.66 (13)	C1—C6—C7—C8	17.5 (3)
O1—S1—N1—C8	−59.96 (15)	O3—C7—C8—N1	−178.49 (17)
C1—S1—N1—C8	54.02 (15)	C6—C7—C8—N1	1.4 (3)
O2—S1—N1—C10	32.92 (18)	O3—C7—C8—C9	0.1 (3)
O1—S1—N1—C10	163.30 (15)	C6—C7—C8—C9	179.90 (18)
C1—S1—N1—C10	−82.72 (16)	C10—N1—C8—C7	96.1 (2)
O2—S1—C1—C2	29.0 (2)	S1—N1—C8—C7	−41.2 (2)
O1—S1—C1—C2	−103.00 (19)	C10—N1—C8—C9	−82.5 (2)
N1—S1—C1—C2	143.52 (18)	S1—N1—C8—C9	140.21 (16)
O2—S1—C1—C6	−151.62 (16)	C11—N2—C9—O4	0.2 (3)
O1—S1—C1—C6	76.36 (17)	C11—N2—C9—C8	179.09 (18)
N1—S1—C1—C6	−37.12 (18)	C7—C8—C9—O4	−4.3 (3)
C6—C1—C2—C3	−0.7 (3)	N1—C8—C9—O4	174.32 (18)
S1—C1—C2—C3	178.60 (17)	C7—C8—C9—N2	176.80 (18)
C1—C2—C3—C4	−0.8 (3)	N1—C8—C9—N2	−4.6 (3)
C2—C3—C4—C5	0.8 (3)	C9—N2—C11—C12	23.9 (3)
C3—C4—C5—C6	0.8 (3)	C9—N2—C11—C16	−156.9 (2)
C4—C5—C6—C1	−2.2 (3)	C16—C11—C12—C13	0.6 (3)
C4—C5—C6—C7	175.80 (19)	N2—C11—C12—C13	179.77 (19)
C2—C1—C6—C5	2.2 (3)	C11—C12—C13—C14	−0.7 (3)
S1—C1—C6—C5	−177.17 (15)	C12—C13—C14—C15	0.3 (4)
C2—C1—C6—C7	−175.82 (19)	C13—C14—C15—C16	0.2 (4)
S1—C1—C6—C7	4.8 (3)	C14—C15—C16—C11	−0.2 (4)
C5—C6—C7—O3	19.4 (3)	C12—C11—C16—C15	−0.2 (3)
C1—C6—C7—O3	−162.66 (18)	N2—C11—C16—C15	−179.3 (2)
C5—C6—C7—C8	−160.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1ⁱ	0.88	2.26	2.987 (2)	140
C3—H3···O2ⁱⁱ	0.95	2.48	3.300 (3)	145
C13—H13···O4ⁱⁱⁱ	0.95	2.48	3.339 (3)	151
N2—H2N···N1	0.88	2.27	2.724 (2)	112
O3—H3O···O4	0.84	1.79	2.534 (2)	146
C12—H12···O4	0.95	2.36	2.902 (3)	116

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂O₄S
M_r	330.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	10.502 (2), 7.649 (3), 19.235 (4)
β (°)	103.395 (15)
V (Å³)	1503.1 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.10 × 0.08 × 0.07

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.977, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	12580, 3450, 2901
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.119, 1.06
No. of reflections	3450
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.31

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1ⁱ	0.88	2.26	2.987 (2)	140.0
C3—H3···O2ⁱⁱ	0.95	2.48	3.300 (3)	145.2
C13—H13···O4ⁱⁱⁱ	0.95	2.48	3.339 (3)	150.7
O3—H3O···O4	0.84	1.79	2.534 (2)	145.9

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

Acknowledgements

The authors are grateful to the Higher Education Commission, Pakistan, and the Institute of Chemistry, University of the Punjab, Lahore, Pakistan, for financial support.

References

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