4-Methyl-N-(4-nitro­benzo­yl)benzene­sulfonamide

Suchetan, P.A.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536811009470

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o917

doi:10.1107/S1600536811009470

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4-Methyl-N-(4-nitrobenzoyl)benzenesulfonamide

P. A. Suchetan,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 4 March 2011; accepted 12 March 2011; online 19 March 2011)

In title compound, C₁₄H₁₂N₂O₅S, the dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 81.5 (2)° and that between the sulfonyl and the benzoyl benzene rings is 89.8 (1)°. In the crystal, molecules are linked into chains along the b axis via intermolecular N—H⋯O hydrogen bonds. C—H⋯O interactions are also observed.

Related literature

For background to our study of the effect of substituents on the structures of methanesulfonamides, see: Gowda et al. (2007 ). For the effect of substituents on the structures of N-(aryl)-arylsulfonamides, see: Gowda et al. (2005 ). For the effect of substituents on the structures of N-(p-substituted benzoyl)-p-substituted benzenesulfonamides, see: Suchetan et al. (2010a ,b ).

Experimental

Crystal data

C₁₄H₁₂N₂O₅S
M_r = 320.32
Monoclinic, P 2₁
a = 11.722 (3) Å
b = 5.137 (1) Å
c = 12.488 (3) Å
β = 105.09 (2)°
V = 726.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.40 × 0.12 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.907, T_max = 0.980
2664 measured reflections
2265 independent reflections
1993 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.128
S = 1.17
2265 reflections
203 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.36 e Å⁻³
Absolute structure: Flack (1983 ), 605 Friedel pairs
Flack parameter: −0.05 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.85 (3)	2.22 (3)	3.054 (4)	164 (4)
N1—H1N⋯O1ⁱⁱ	0.85 (3)	2.54 (4)	2.944 (5)	110 (3)
C9—H9⋯O3ⁱⁱⁱ	0.93	2.58	3.254 (5)	130
C13—H13⋯O2ⁱ	0.93	2.53	3.347 (5)	147
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (ii) x, y+1, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009470/vm2084sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009470/vm2084Isup2.hkl

checkCIF report

Comment top

The amide and sulfonamide moieties are important constituents of many biologically significant compounds. As a part of studying the effect of substituents on the structures of this class of compounds (Gowda et al., 2005, 2007; Suchetan et al., 2010a,b), the structure of 4-methyl-N-(4-nitrobenzoyl)-benzenesulfonamide (I) has been determined. The conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C=O bond (Fig.1), similar to those observed in N-(4-chlorobenzoyl)-4- methylbenzenesulfonamide (II) (Suchetan et al., 2010a) and 4-methyl-N-(4-methylbenzoyl)-benzenesulfonamide (III) (Suchetan et al., 2010b).

The molecules are twisted at the S atoms with the C—S(O₂)—NH—C(O) torsional angle of 58.7 (3)°, compared to the values of 67.1 (2)° (molecule 1) and 67.7 (2)° (molecule 2) in (II) and 62.0 (2)° in (III).

The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 81.5 (2)°, compared to the values of 83.6 (1)° (molecule 1) and 81.0 (1)° (molecule 2) in (II) and 84.9 (1)° in (III).

The dihedral angle between the sulfonyl and the benzoyl benzene rings is 89.8 (1)°, compared to the values of 81.0 (1)° (molecule 1) and 76.3 (1)° (molecule 2) in (II) and 89.0 (1)° in (III).

In the crystal packing the molecules are linked by intermolecular N—H···O hydrogen bonds (Table 1, Fig. 2). Two C—H···O interactions are also observed.

Related literature top

For background to our study of the effect of substituents on the structures of methanesulfonamides, see: Gowda et al. (2007). For the effect of substituents in N-(aryl)-arylsulfonamides, see: Gowda et al. (2005). For the effect of substituents on the structures of N-(p-substituted benzoyl)-p-substituted benzenesulfonamides, see: Suchetan et al. (2010a,b).

Experimental top

The title compound was prepared by refluxing a mixture of 4-nitrobenzoic acid, 4-methylbenzenesulfonamide and phosphorous oxychloride for 3 hr on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. It was filtered, dried and recrystallized.

The rod like colourless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of a toluene solution at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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. Molecular structure of the title compound, showing the atom- labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.

4-Methyl-N-(4-nitrobenzoyl)benzenesulfonamide top

Crystal data top

C₁₄H₁₂N₂O₅S	F(000) = 332
M_r = 320.32	D_x = 1.465 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1463 reflections
a = 11.722 (3) Å	θ = 2.8–27.9°
b = 5.137 (1) Å	µ = 0.25 mm⁻¹
c = 12.488 (3) Å	T = 293 K
β = 105.09 (2)°	Rod, colourless
V = 726.0 (3) Å³	0.40 × 0.12 × 0.08 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2265 independent reflections
Radiation source: fine-focus sealed tube	1993 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→14
T_min = 0.907, T_max = 0.980	k = −4→6
2664 measured reflections	l = −15→12

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)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.0525P)² + 0.6019P] where P = (F_o² + 2F_c²)/3
S = 1.17	(Δ/σ)_max = 0.001
2265 reflections	Δρ_max = 0.26 e Å⁻³
203 parameters	Δρ_min = −0.36 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 605 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (14)

Crystal data top

C₁₄H₁₂N₂O₅S	V = 726.0 (3) Å³
M_r = 320.32	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.722 (3) Å	µ = 0.25 mm⁻¹
b = 5.137 (1) Å	T = 293 K
c = 12.488 (3) Å	0.40 × 0.12 × 0.08 mm
β = 105.09 (2)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2265 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1993 reflections with I > 2σ(I)
T_min = 0.907, T_max = 0.980	R_int = 0.030
2664 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.128	Δρ_max = 0.26 e Å⁻³
S = 1.17	Δρ_min = −0.36 e Å⁻³
2265 reflections	Absolute structure: Flack (1983), 605 Friedel pairs
203 parameters	Absolute structure parameter: −0.05 (14)
2 restraints

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
C1	0.2737 (4)	0.1687 (9)	0.1307 (3)	0.0362 (9)
C2	0.2176 (4)	0.3782 (10)	0.0686 (4)	0.0460 (11)
H2	0.2510	0.4608	0.0178	0.055*
C3	0.1097 (4)	0.4617 (11)	0.0842 (4)	0.0532 (13)
H3	0.0708	0.6011	0.0428	0.064*
C4	0.0597 (4)	0.3414 (10)	0.1600 (4)	0.0481 (12)
C5	0.1184 (4)	0.1350 (11)	0.2208 (4)	0.0522 (13)
H5	0.0853	0.0517	0.2716	0.063*
C6	0.2260 (4)	0.0498 (12)	0.2073 (3)	0.0438 (9)
H6	0.2655	−0.0871	0.2500	0.053*
C7	0.5340 (4)	0.3078 (9)	0.2885 (3)	0.0371 (10)
C8	0.6231 (3)	0.5138 (8)	0.3373 (3)	0.0343 (10)
C9	0.6277 (4)	0.5947 (12)	0.4452 (3)	0.0509 (12)
H9	0.5779	0.5190	0.4834	0.061*
C10	0.7056 (5)	0.7857 (11)	0.4949 (4)	0.0549 (14)
H10	0.7075	0.8438	0.5658	0.066*
C11	0.7808 (4)	0.8898 (10)	0.4380 (4)	0.0449 (11)
C12	0.7788 (4)	0.8124 (10)	0.3324 (4)	0.0499 (12)
H12	0.8301	0.8864	0.2953	0.060*
C13	0.6993 (4)	0.6224 (10)	0.2822 (3)	0.0469 (13)
H13	0.6972	0.5672	0.2108	0.056*
C14	−0.0577 (4)	0.4337 (15)	0.1747 (5)	0.0717 (17)
H14A	−0.1132	0.2924	0.1602	0.086*
H14B	−0.0869	0.5734	0.1238	0.086*
H14C	−0.0476	0.4941	0.2493	0.086*
N1	0.5123 (3)	0.2647 (7)	0.1742 (3)	0.0329 (8)
H1N	0.525 (4)	0.377 (8)	0.129 (3)	0.039*
N2	0.8665 (4)	1.0941 (10)	0.4911 (3)	0.0568 (11)
O1	0.4318 (3)	−0.1903 (6)	0.1572 (3)	0.0502 (8)
O2	0.4040 (3)	0.0951 (7)	−0.0061 (2)	0.0487 (8)
O3	0.4829 (3)	0.1812 (7)	0.3440 (2)	0.0542 (9)
O4	0.9267 (4)	1.1940 (9)	0.4363 (4)	0.0806 (13)
O5	0.8702 (4)	1.1530 (10)	0.5865 (3)	0.0890 (15)
S1	0.40811 (9)	0.0583 (2)	0.10898 (7)	0.0359 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.040 (2)	0.035 (2)	0.0326 (19)	0.0028 (19)	0.0070 (16)	−0.0031 (18)
C2	0.048 (3)	0.039 (3)	0.050 (3)	−0.002 (2)	0.013 (2)	0.001 (2)
C3	0.052 (3)	0.053 (3)	0.049 (3)	0.015 (2)	0.003 (2)	0.010 (2)
C4	0.041 (2)	0.061 (3)	0.038 (2)	0.003 (2)	0.0028 (19)	−0.006 (2)
C5	0.047 (2)	0.065 (4)	0.046 (2)	−0.002 (2)	0.0154 (19)	0.003 (2)
C6	0.048 (2)	0.045 (2)	0.0384 (19)	0.003 (3)	0.0112 (17)	0.005 (3)
C7	0.038 (2)	0.044 (3)	0.031 (2)	0.006 (2)	0.0105 (17)	0.0044 (19)
C8	0.0359 (19)	0.039 (3)	0.0254 (16)	0.0066 (19)	0.0035 (14)	−0.0010 (17)
C9	0.058 (3)	0.063 (4)	0.0313 (19)	−0.005 (3)	0.0122 (18)	0.000 (2)
C10	0.073 (3)	0.058 (4)	0.031 (2)	0.001 (3)	0.009 (2)	−0.007 (2)
C11	0.047 (2)	0.038 (3)	0.043 (2)	0.008 (2)	−0.001 (2)	0.002 (2)
C12	0.051 (3)	0.057 (3)	0.044 (2)	−0.011 (2)	0.015 (2)	−0.008 (2)
C13	0.047 (2)	0.063 (4)	0.0330 (19)	−0.005 (2)	0.0133 (18)	−0.008 (2)
C14	0.049 (3)	0.099 (5)	0.066 (3)	0.018 (3)	0.013 (3)	−0.001 (3)
N1	0.0442 (19)	0.030 (2)	0.0241 (16)	0.0003 (16)	0.0081 (14)	0.0031 (13)
N2	0.064 (2)	0.047 (3)	0.048 (2)	0.002 (2)	−0.0050 (18)	−0.005 (2)
O1	0.053 (2)	0.037 (2)	0.061 (2)	0.0047 (16)	0.0156 (15)	−0.0032 (15)
O2	0.0562 (17)	0.060 (2)	0.0305 (13)	−0.0034 (18)	0.0115 (12)	−0.0111 (16)
O3	0.062 (2)	0.069 (2)	0.0339 (15)	−0.0161 (19)	0.0162 (14)	0.0028 (16)
O4	0.080 (3)	0.077 (3)	0.074 (3)	−0.031 (3)	0.002 (2)	−0.004 (2)
O5	0.113 (3)	0.089 (4)	0.056 (2)	−0.019 (3)	0.006 (2)	−0.029 (2)
S1	0.0428 (5)	0.0325 (5)	0.0324 (4)	0.0018 (6)	0.0099 (4)	−0.0027 (5)

Geometric parameters (Å, º) top

C1—C6	1.371 (6)	C9—H9	0.9300
C1—C2	1.388 (6)	C10—C11	1.376 (7)
C1—S1	1.761 (4)	C10—H10	0.9300
C2—C3	1.396 (6)	C11—C12	1.372 (6)
C2—H2	0.9300	C11—N2	1.485 (6)
C3—C4	1.383 (7)	C12—C13	1.382 (6)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.379 (7)	C13—H13	0.9300
C4—C14	1.511 (7)	C14—H14A	0.9600
C5—C6	1.385 (6)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—H6	0.9300	N1—S1	1.661 (4)
C7—O3	1.215 (5)	N1—H1N	0.85 (3)
C7—N1	1.401 (5)	N2—O4	1.217 (6)
C7—C8	1.500 (6)	N2—O5	1.219 (5)
C8—C13	1.379 (6)	O1—S1	1.409 (3)
C8—C9	1.398 (5)	O2—S1	1.438 (3)
C9—C10	1.374 (7)

C6—C1—C2	121.0 (4)	C11—C10—H10	120.5
C6—C1—S1	120.5 (4)	C12—C11—C10	122.1 (5)
C2—C1—S1	118.4 (3)	C12—C11—N2	118.3 (4)
C1—C2—C3	118.3 (4)	C10—C11—N2	119.6 (4)
C1—C2—H2	120.8	C11—C12—C13	118.7 (4)
C3—C2—H2	120.8	C11—C12—H12	120.6
C4—C3—C2	121.3 (5)	C13—C12—H12	120.6
C4—C3—H3	119.4	C8—C13—C12	120.5 (4)
C2—C3—H3	119.4	C8—C13—H13	119.7
C5—C4—C3	118.7 (4)	C12—C13—H13	119.7
C5—C4—C14	121.0 (5)	C4—C14—H14A	109.5
C3—C4—C14	120.3 (5)	C4—C14—H14B	109.5
C4—C5—C6	121.1 (4)	H14A—C14—H14B	109.5
C4—C5—H5	119.5	C4—C14—H14C	109.5
C6—C5—H5	119.5	H14A—C14—H14C	109.5
C1—C6—C5	119.5 (5)	H14B—C14—H14C	109.5
C1—C6—H6	120.2	C7—N1—S1	121.0 (3)
C5—C6—H6	120.2	C7—N1—H1N	124 (3)
O3—C7—N1	120.7 (4)	S1—N1—H1N	110 (3)
O3—C7—C8	122.7 (4)	O4—N2—O5	124.5 (5)
N1—C7—C8	116.6 (3)	O4—N2—C11	118.1 (4)
C13—C8—C9	119.5 (4)	O5—N2—C11	117.4 (5)
C13—C8—C7	123.8 (3)	O1—S1—O2	119.9 (2)
C9—C8—C7	116.7 (4)	O1—S1—N1	109.32 (19)
C10—C9—C8	120.1 (4)	O2—S1—N1	103.62 (18)
C10—C9—H9	119.9	O1—S1—C1	108.1 (2)
C8—C9—H9	119.9	O2—S1—C1	108.24 (19)
C9—C10—C11	119.0 (4)	N1—S1—C1	106.99 (19)
C9—C10—H10	120.5

C6—C1—C2—C3	−1.4 (7)	N2—C11—C12—C13	−180.0 (4)
S1—C1—C2—C3	178.6 (4)	C9—C8—C13—C12	−0.9 (7)
C1—C2—C3—C4	0.5 (7)	C7—C8—C13—C12	179.7 (4)
C2—C3—C4—C5	0.0 (7)	C11—C12—C13—C8	0.3 (7)
C2—C3—C4—C14	−179.4 (5)	O3—C7—N1—S1	5.4 (5)
C3—C4—C5—C6	0.5 (7)	C8—C7—N1—S1	−175.2 (3)
C14—C4—C5—C6	179.9 (5)	C12—C11—N2—O4	4.0 (7)
C2—C1—C6—C5	1.9 (7)	C10—C11—N2—O4	−175.5 (5)
S1—C1—C6—C5	−178.1 (4)	C12—C11—N2—O5	−177.1 (5)
C4—C5—C6—C1	−1.4 (7)	C10—C11—N2—O5	3.4 (7)
O3—C7—C8—C13	166.2 (4)	C7—N1—S1—O1	−58.2 (4)
N1—C7—C8—C13	−13.2 (6)	C7—N1—S1—O2	172.9 (3)
O3—C7—C8—C9	−13.2 (6)	C7—N1—S1—C1	58.7 (3)
N1—C7—C8—C9	167.4 (4)	C6—C1—S1—O1	15.4 (4)
C13—C8—C9—C10	1.7 (7)	C2—C1—S1—O1	−164.7 (3)
C7—C8—C9—C10	−178.9 (4)	C6—C1—S1—O2	146.7 (4)
C8—C9—C10—C11	−1.9 (8)	C2—C1—S1—O2	−33.4 (4)
C9—C10—C11—C12	1.3 (8)	C6—C1—S1—N1	−102.2 (4)
C9—C10—C11—N2	−179.3 (4)	C2—C1—S1—N1	77.7 (4)
C10—C11—C12—C13	−0.5 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.85 (3)	2.22 (3)	3.054 (4)	164 (4)
N1—H1N···O1ⁱⁱ	0.85 (3)	2.54 (4)	2.944 (5)	110 (3)
C9—H9···O3ⁱⁱⁱ	0.93	2.58	3.254 (5)	130
C13—H13···O2ⁱ	0.93	2.53	3.347 (5)	147

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂N₂O₅S
M_r	320.32
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	11.722 (3), 5.137 (1), 12.488 (3)
β (°)	105.09 (2)
V (Å³)	726.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.40 × 0.12 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.907, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	2664, 2265, 1993
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.128, 1.17
No. of reflections	2265
No. of parameters	203
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.36
Absolute structure	Flack (1983), 605 Friedel pairs
Absolute structure parameter	−0.05 (14)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.85 (3)	2.22 (3)	3.054 (4)	164 (4)
N1—H1N···O1ⁱⁱ	0.85 (3)	2.54 (4)	2.944 (5)	110 (3)
C9—H9···O3ⁱⁱⁱ	0.93	2.58	3.254 (5)	130
C13—H13···O2ⁱ	0.93	2.53	3.347 (5)	147

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

Acknowledgements

PAS thanks the Council of Scientific and Industrial Research (CSIR), Government of India, New Delhi, for the award of a research fellowship.

References

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