4-Methyl-2-(2-nitro­benzene­sulfon­amido)­penta­noic acid

Arshad, M.N.; Danish, M.; Tahir, M.N.; Khalid, S.; Asiri, A.M.

doi:10.1107/S1600536812033260

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2573

https://doi.org/10.1107/S1600536812033260

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4-Methyl-2-(2-nitrobenzenesulfonamido)pentanoic acid

Muhammad Nadeem Arshad,^a Muhammad Danish,^b ^* Muhammad Nawaz Tahir,^c Savera Khalid ^b and Abdullah M. Asiri ^d,^a

^aThe Center of Excellence for Advanced Materials Research (CEAMR), Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, ^bDepartment of Chemistry, University of Gujrat, Gujrat 50700, Pakistan, ^cDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^dDepartment of Chemistry, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia
^*Correspondence e-mail: drdanish62@gmail.com

(Received 10 July 2012; accepted 23 July 2012; online 28 July 2012)

In the title compound, C₁₂H₁₆N₂O₆S, the S atom adopts a distorted tetrahedral geometry with an O—S—O angle of 119.76 (13)°. The nitro group is twisted by 35.34 (2)° with respect to the aromatic ring; it accepts an N—H⋯O hydrogen bond, resulting in a S(7) motif. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds connect the molecules into an infinite chain along the a axis. The methyl C atoms of the isopropyl group are disordered in a 1:1 ratio.

Related literature

For a related structure, see: Arshad et al. (2010 ), For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₂H₁₆N₂O₆S
M_r = 316.33
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.9593 (5) Å
b = 10.7560 (8) Å
c = 20.8431 (14) Å
V = 1560.19 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.45 × 0.38 × 0.29 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.902, T_max = 0.935
11203 measured reflections
2730 independent reflections
2029 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.090
S = 0.99
2730 reflections
212 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ), 1117 Friedel pairs
Flack parameter: 0.07 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O2	0.85 (1)	2.34 (4)	2.937 (3)	128 (4)
O6—H6O⋯O5ⁱ	0.85 (1)	1.87 (2)	2.702 (3)	166 (5)
N2—H2N⋯O5ⁱⁱ	0.85 (1)	2.38 (2)	3.169 (3)	155 (4)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812033260/ng5283sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812033260/ng5283Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812033260/ng5283Isup3.cml

checkCIF report

Comment top

In order to explore the structural behaviour of sulfonamide derived from amino acids (Arshad et al., 2010), here we report the crystal structure of title compound.

The nitro group attached to aromatic ring is twisted at dihedral angle of 35.34 (2)°, with the maximum deviation from the two oxygen atoms being -0.532 (6) Å for O1 and 0.703 (5) Å for O2. An intramolecular N—H···O leads to the formation of a seven membered ring motif, S₁¹(7) (Bernstein et al., 1995). The nitro group is oriented at an angle of 29.84 (6)° with respect to aromatic ring. Adjacent molecules are linked to form an infinite chain along a axis through O—H···O and N—H···O interactions (Table. 1, Fig. 2).

Related literature top

For a related structure, see: Arshad et al. (2010), For graph-set notation, see: Bernstein et al. (1995).

Experimental top

L-lucine (0.20 g, 0.089 mmole) dissolved in 5–10 mL distilled water was treated with sodium carbonate (1M) to a pH of 8–9. 2-Nitrobenzenesulphonyl chloride (0.117 g, 0.089 mmole) added within 3–5 min. The pH was adjusted by sodium carbonate (1M). Then, dilute HCl was added dropwise to result in a pH 2–3. The precipitate was filtered, washed with plenty of water and dried. Suitable crystals was obtained upon recrystalization in methanol.

Structure description top

In order to explore the structural behaviour of sulfonamide derived from amino acids (Arshad et al., 2010), here we report the crystal structure of title compound.

For a related structure, see: Arshad et al. (2010), For graph-set notation, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The labelled molecular structure of (I) with 50% displacement ellipsoids.
	Fig. 2. Unit cell packing showing hydrogen bonds, drawn using dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.

4-Methyl-2-(2-nitrobenzenesulfonamido)pentanoic acid top

Crystal data top

C₁₂H₁₆N₂O₆S	F(000) = 664
M_r = 316.33	D_x = 1.347 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1789 reflections
a = 6.9593 (5) Å	θ = 2.7–19.5°
b = 10.7560 (8) Å	µ = 0.23 mm⁻¹
c = 20.8431 (14) Å	T = 296 K
V = 1560.19 (19) Å³	Prismatic, colorless
Z = 4	0.45 × 0.38 × 0.29 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2730 independent reflections
Radiation source: fine-focus sealed tube	2029 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
φ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→8
T_min = 0.902, T_max = 0.935	k = −12→12
11203 measured reflections	l = −24→24

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.090	w = 1/[σ²(F_o²) + (0.041P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
2730 reflections	Δρ_max = 0.15 e Å⁻³
212 parameters	Δρ_min = −0.20 e Å⁻³
10 restraints	Absolute structure: Flack (1983), 1117 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.07 (10)

Crystal data top

C₁₂H₁₆N₂O₆S	V = 1560.19 (19) Å³
M_r = 316.33	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.9593 (5) Å	µ = 0.23 mm⁻¹
b = 10.7560 (8) Å	T = 296 K
c = 20.8431 (14) Å	0.45 × 0.38 × 0.29 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2730 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2029 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.935	R_int = 0.045
11203 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.090	Δρ_max = 0.15 e Å⁻³
S = 0.99	Δρ_min = −0.20 e Å⁻³
2730 reflections	Absolute structure: Flack (1983), 1117 Friedel pairs
212 parameters	Absolute structure parameter: 0.07 (10)
10 restraints

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	Occ. (<1)
S1	0.85210 (10)	0.49317 (7)	0.11950 (3)	0.0477 (2)
O1	0.6834 (3)	0.8270 (3)	0.21732 (13)	0.0947 (9)
N1	0.7618 (4)	0.7669 (3)	0.17531 (14)	0.0577 (7)
C1	1.0039 (4)	0.5944 (3)	0.16432 (12)	0.0445 (7)
O2	0.6943 (3)	0.7525 (2)	0.12226 (12)	0.0783 (7)
N2	0.8391 (4)	0.5420 (2)	0.04664 (11)	0.0433 (6)
C2	0.9481 (4)	0.7099 (3)	0.18997 (13)	0.0460 (8)
O3	0.6652 (3)	0.5002 (2)	0.14685 (10)	0.0691 (6)
C3	1.0679 (5)	0.7759 (3)	0.22962 (15)	0.0663 (10)
H3	1.0269	0.8509	0.2471	0.080*
O4	0.9507 (3)	0.37724 (17)	0.11794 (10)	0.0633 (6)
C4	1.2476 (5)	0.7316 (4)	0.24342 (17)	0.0794 (12)
H4	1.3294	0.7770	0.2698	0.095*
O5	1.1024 (3)	0.73707 (19)	0.01558 (9)	0.0505 (6)
C5	1.3060 (5)	0.6211 (4)	0.21847 (17)	0.0757 (11)
H5	1.4283	0.5913	0.2278	0.091*
O6	1.3184 (3)	0.5923 (2)	−0.00802 (12)	0.0610 (6)
C6	1.1854 (5)	0.5525 (3)	0.17923 (14)	0.0569 (9)
H6	1.2276	0.4769	0.1627	0.068*
C12	1.1431 (4)	0.6294 (3)	0.00506 (12)	0.0429 (7)
C7A	1.0001 (4)	0.5234 (2)	0.00245 (13)	0.0401 (7)	0.50
H7A	1.0676	0.4480	0.0161	0.048*	0.50
C8A	0.938 (3)	0.504 (2)	−0.0676 (7)	0.046 (3)	0.50
H81	0.8773	0.5793	−0.0830	0.056*	0.50
H82	1.0510	0.4890	−0.0936	0.056*	0.50
C9A	0.798 (5)	0.395 (3)	−0.0769 (14)	0.0651 (12)	0.50
H9A	0.7104	0.3945	−0.0400	0.078*	0.50
C10A	0.676 (4)	0.413 (4)	−0.1372 (12)	0.104 (7)	0.50
H10A	0.5886	0.4815	−0.1308	0.156*	0.50
H10B	0.6040	0.3390	−0.1457	0.156*	0.50
H10C	0.7580	0.4312	−0.1730	0.156*	0.50
C11A	0.903 (9)	0.272 (3)	−0.077 (3)	0.116 (7)	0.50
H11A	0.9924	0.2710	−0.1126	0.174*	0.50
H11B	0.8124	0.2058	−0.0824	0.174*	0.50
H11C	0.9716	0.2622	−0.0378	0.174*	0.50
C7B	1.0001 (4)	0.5234 (2)	0.00245 (13)	0.0401 (7)	0.50
H7B	1.0645	0.4444	0.0117	0.048*	0.50
C8B	0.910 (4)	0.520 (2)	−0.0647 (7)	0.046 (3)	0.50
H83	0.8243	0.5907	−0.0693	0.056*	0.50
H84	1.0109	0.5285	−0.0964	0.056*	0.50
C9B	0.797 (5)	0.401 (3)	−0.0783 (13)	0.0651 (12)	0.50
H9B	0.6792	0.4034	−0.0527	0.078*	0.50
C10B	0.739 (4)	0.398 (4)	−0.1495 (12)	0.104 (7)	0.50
H10D	0.6714	0.4726	−0.1601	0.156*	0.50
H10E	0.6568	0.3273	−0.1570	0.156*	0.50
H10F	0.8518	0.3907	−0.1756	0.156*	0.50
C11B	0.905 (9)	0.283 (3)	−0.061 (3)	0.116 (7)	0.50
H11D	1.0278	0.2832	−0.0812	0.174*	0.50
H11E	0.8321	0.2123	−0.0743	0.174*	0.50
H11F	0.9217	0.2803	−0.0149	0.174*	0.50
H2N	0.780 (5)	0.611 (2)	0.042 (2)	0.139*
H6O	1.393 (6)	0.655 (3)	−0.013 (3)	0.174*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0575 (4)	0.0422 (4)	0.0435 (4)	−0.0031 (4)	0.0088 (4)	0.0032 (4)
O1	0.0808 (18)	0.107 (2)	0.096 (2)	0.0244 (16)	0.0092 (15)	−0.0496 (17)
N1	0.0688 (18)	0.0496 (18)	0.0548 (19)	0.0067 (14)	0.0099 (16)	−0.0070 (15)
C1	0.0542 (19)	0.0466 (19)	0.0328 (16)	0.0021 (16)	0.0081 (14)	0.0022 (14)
O2	0.0921 (16)	0.0889 (18)	0.0541 (14)	0.0387 (14)	−0.0074 (14)	0.0009 (14)
N2	0.0490 (14)	0.0458 (15)	0.0351 (13)	0.0012 (11)	0.0038 (12)	−0.0004 (11)
C2	0.0512 (17)	0.052 (2)	0.0349 (16)	0.0026 (16)	0.0075 (14)	0.0006 (15)
O3	0.0682 (14)	0.0802 (16)	0.0589 (13)	−0.0165 (15)	0.0231 (11)	−0.0023 (12)
C3	0.075 (2)	0.068 (2)	0.055 (2)	−0.004 (2)	0.0129 (18)	−0.019 (2)
O4	0.0946 (16)	0.0380 (13)	0.0574 (13)	0.0074 (10)	0.0061 (13)	0.0052 (11)
C4	0.062 (2)	0.106 (3)	0.070 (3)	−0.012 (2)	0.005 (2)	−0.034 (2)
O5	0.0464 (11)	0.0390 (13)	0.0661 (15)	−0.0011 (9)	0.0019 (10)	−0.0059 (11)
C5	0.058 (2)	0.108 (3)	0.061 (2)	0.012 (2)	−0.0014 (18)	−0.014 (2)
O6	0.0413 (13)	0.0466 (13)	0.0952 (17)	0.0033 (10)	0.0060 (12)	−0.0068 (13)
C6	0.058 (2)	0.071 (2)	0.0417 (18)	0.0103 (17)	0.0038 (16)	−0.0035 (16)
C12	0.0466 (16)	0.0431 (19)	0.0391 (17)	0.0025 (14)	−0.0021 (15)	−0.0025 (14)
C7A	0.0409 (15)	0.0398 (17)	0.0396 (15)	−0.0010 (13)	0.0078 (12)	−0.0005 (14)
C8A	0.053 (5)	0.042 (5)	0.044 (2)	−0.005 (4)	0.008 (3)	−0.009 (2)
C9A	0.085 (2)	0.058 (3)	0.052 (2)	−0.029 (2)	−0.0011 (19)	−0.007 (2)
C10A	0.143 (16)	0.115 (10)	0.055 (9)	−0.066 (13)	−0.013 (10)	−0.011 (6)
C11A	0.146 (4)	0.049 (5)	0.15 (2)	−0.017 (5)	−0.031 (13)	−0.046 (7)
C7B	0.0409 (15)	0.0398 (17)	0.0396 (15)	−0.0010 (13)	0.0078 (12)	−0.0005 (14)
C8B	0.053 (5)	0.042 (5)	0.044 (2)	−0.005 (4)	0.008 (3)	−0.009 (2)
C9B	0.085 (2)	0.058 (3)	0.052 (2)	−0.029 (2)	−0.0011 (19)	−0.007 (2)
C10B	0.143 (16)	0.115 (10)	0.055 (9)	−0.066 (13)	−0.013 (10)	−0.011 (6)
C11B	0.146 (4)	0.049 (5)	0.15 (2)	−0.017 (5)	−0.031 (13)	−0.046 (7)

Geometric parameters (Å, º) top

S1—O3	1.422 (2)	C8A—C9A	1.532 (12)
S1—O4	1.424 (2)	C8A—H81	0.9700
S1—N2	1.609 (2)	C8A—H82	0.9700
S1—C1	1.781 (3)	C9A—C11A	1.511 (13)
O1—N1	1.217 (3)	C9A—C10A	1.531 (13)
N1—O2	1.211 (3)	C9A—H9A	0.9800
N1—C2	1.466 (4)	C10A—H10A	0.9600
C1—C6	1.376 (4)	C10A—H10B	0.9600
C1—C2	1.408 (4)	C10A—H10C	0.9600
N2—C7A	1.464 (3)	C11A—H11A	0.9600
N2—H2N	0.850 (10)	C11A—H11B	0.9600
C2—C3	1.372 (4)	C11A—H11C	0.9600
C3—C4	1.369 (5)	C8B—C9B	1.530 (11)
C3—H3	0.9300	C8B—H83	0.9700
C4—C5	1.360 (5)	C8B—H84	0.9700
C4—H4	0.9300	C9B—C11B	1.513 (12)
O5—C12	1.212 (3)	C9B—C10B	1.538 (14)
C5—C6	1.385 (4)	C9B—H9B	0.9800
C5—H5	0.9300	C10B—H10D	0.9600
O6—C12	1.312 (3)	C10B—H10E	0.9600
O6—H6O	0.852 (10)	C10B—H10F	0.9600
C6—H6	0.9300	C11B—H11D	0.9600
C12—C7A	1.514 (4)	C11B—H11E	0.9600
C7A—C8A	1.538 (11)	C11B—H11F	0.9600
C7A—H7A	0.9800

O3—S1—O4	119.76 (13)	N2—C7A—H7A	107.3
O3—S1—N2	108.02 (13)	C12—C7A—H7A	107.3
O4—S1—N2	106.94 (13)	C8A—C7A—H7A	107.3
O3—S1—C1	107.46 (13)	C9A—C8A—C7A	113.8 (14)
O4—S1—C1	105.15 (14)	C9A—C8A—H81	108.8
N2—S1—C1	109.20 (13)	C7A—C8A—H81	108.8
O2—N1—O1	123.4 (3)	C9A—C8A—H82	108.8
O2—N1—C2	118.7 (3)	C7A—C8A—H82	108.8
O1—N1—C2	118.0 (3)	H81—C8A—H82	107.7
C6—C1—C2	117.2 (3)	C11A—C9A—C10A	112.0 (15)
C6—C1—S1	117.6 (2)	C11A—C9A—C8A	111.0 (17)
C2—C1—S1	125.1 (2)	C10A—C9A—C8A	111.0 (15)
C7A—N2—S1	120.39 (19)	C11A—C9A—H9A	107.5
C7A—N2—H2N	115 (3)	C10A—C9A—H9A	107.5
S1—N2—H2N	114 (3)	C8A—C9A—H9A	107.5
C3—C2—C1	121.2 (3)	C9B—C8B—H83	108.9
C3—C2—N1	116.5 (3)	C9B—C8B—H84	108.9
C1—C2—N1	122.3 (3)	H83—C8B—H84	107.7
C4—C3—C2	120.1 (3)	C11B—C9B—C8B	113.7 (15)
C4—C3—H3	120.0	C11B—C9B—C10B	110.3 (16)
C2—C3—H3	120.0	C8B—C9B—C10B	109.5 (16)
C5—C4—C3	119.8 (4)	C11B—C9B—H9B	107.7
C5—C4—H4	120.1	C8B—C9B—H9B	107.7
C3—C4—H4	120.1	C10B—C9B—H9B	107.7
C4—C5—C6	120.7 (3)	C9B—C10B—H10D	109.5
C4—C5—H5	119.7	C9B—C10B—H10E	109.5
C6—C5—H5	119.7	H10D—C10B—H10E	109.5
C12—O6—H6O	111 (4)	C9B—C10B—H10F	109.5
C1—C6—C5	121.0 (3)	H10D—C10B—H10F	109.5
C1—C6—H6	119.5	H10E—C10B—H10F	109.5
C5—C6—H6	119.5	C9B—C11B—H11D	109.5
O5—C12—O6	123.0 (3)	C9B—C11B—H11E	109.5
O5—C12—C7A	124.9 (3)	H11D—C11B—H11E	109.5
O6—C12—C7A	112.0 (2)	C9B—C11B—H11F	109.5
N2—C7A—C12	112.2 (2)	H11D—C11B—H11F	109.5
N2—C7A—C8A	113.6 (10)	H11E—C11B—H11F	109.5
C12—C7A—C8A	108.9 (9)

O3—S1—C1—C6	137.9 (2)	C1—C2—C3—C4	1.9 (5)
O4—S1—C1—C6	9.3 (3)	N1—C2—C3—C4	−177.2 (3)
N2—S1—C1—C6	−105.2 (2)	C2—C3—C4—C5	−0.9 (5)
O3—S1—C1—C2	−36.9 (3)	C3—C4—C5—C6	−0.1 (5)
O4—S1—C1—C2	−165.5 (2)	C2—C1—C6—C5	0.7 (4)
N2—S1—C1—C2	80.0 (3)	S1—C1—C6—C5	−174.5 (2)
O3—S1—N2—C7A	−168.2 (2)	C4—C5—C6—C1	0.2 (5)
O4—S1—N2—C7A	−38.0 (2)	S1—N2—C7A—C12	−88.8 (2)
C1—S1—N2—C7A	75.3 (2)	S1—N2—C7A—C8A	147.2 (10)
C6—C1—C2—C3	−1.8 (4)	O5—C12—C7A—N2	−32.7 (4)
S1—C1—C2—C3	173.0 (2)	O6—C12—C7A—N2	149.8 (2)
C6—C1—C2—N1	177.3 (3)	O5—C12—C7A—C8A	93.8 (11)
S1—C1—C2—N1	−7.9 (4)	O6—C12—C7A—C8A	−83.6 (11)
O2—N1—C2—C3	144.3 (3)	N2—C7A—C8A—C9A	−56 (2)
O1—N1—C2—C3	−35.4 (4)	C12—C7A—C8A—C9A	177.8 (18)
O2—N1—C2—C1	−34.8 (4)	C7A—C8A—C9A—C11A	−80 (3)
O1—N1—C2—C1	145.5 (3)	C7A—C8A—C9A—C10A	155 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O2	0.85 (1)	2.34 (4)	2.937 (3)	128 (4)
O6—H6O···O5ⁱ	0.85 (1)	1.87 (2)	2.702 (3)	166 (5)
N2—H2N···O5ⁱⁱ	0.85 (1)	2.38 (2)	3.169 (3)	155 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₆N₂O₆S
M_r	316.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	6.9593 (5), 10.7560 (8), 20.8431 (14)
V (Å³)	1560.19 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.45 × 0.38 × 0.29

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.902, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	11203, 2730, 2029
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.090, 0.99
No. of reflections	2730
No. of parameters	212
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.20
Absolute structure	Flack (1983), 1117 Friedel pairs
Absolute structure parameter	0.07 (10)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O2	0.850 (10)	2.34 (4)	2.937 (3)	128 (4)
O6—H6O···O5ⁱ	0.852 (10)	1.868 (17)	2.702 (3)	166 (5)
N2—H2N···O5ⁱⁱ	0.850 (10)	2.38 (2)	3.169 (3)	155 (4)

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

Acknowledgements

The authors acknowledge the University of Sargodha for providing diffraction facilities at its Department of Physics.

References

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