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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 2| February 2014| Page o191
doi:10.1107/S1600536814001317

N-(4-Methyl­phenyl­sulfon­yl)-3-nitro­benzamide

S. Sreenivasa,a M. S. Nanjundaswamy,b A. G. Sudha,c K. J. Pampa,d N. K. Lokanathe and P. A. Suchetanf*

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, bDepartment of Chemistry, AVK College for Women, Davangere-2, India, cUniversity College of Science, Tumkur University, Tumkur, India, dDepartment of Studies in Microbiology, University of Mysore, Manasagangotri, Mysore, India, eDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India, and fDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
*Correspondence e-mail: pasuchetan@yahoo.co.in

(Received 15 January 2014; accepted 19 January 2014; online 22 January 2014)

In the title compound, C14H12N2O5S, the dihedral angle between the aromatic rings is 86.29 (1)° and the conformation between the C=O bond of the amide group and the meta-NO2 group is syn. The C—S—N—C torsion angle is −65.87 (19)° and the mol­ecule has an L-shaped conformation. In the crystal, the mol­ecules are connected into inversion dimers through pairs of N—H⋯O hydrogen bonds and C—H⋯O inter­actions forming R22(8) and R22(14) loops, respectively. The dimers are connected by further C—H⋯O inter­actions, thereby forming (100) sheets.

CCDC reference: 978140

Related literature

For related structures see: Suchetan et al. (2010[Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1039.], 2011[Suchetan, P. A., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o917.], 2012[Suchetan, P. A., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o1507.]).

[Scheme 1]

Experimental

Crystal data

  • C14H12N2O5S

  • Mr = 320.32

  • Monoclinic, P 21 /c

  • a = 4.9736 (5) Å

  • b = 23.245 (2) Å

  • c = 12.7197 (11) Å

  • β = 100.820 (4)°

  • V = 1444.4 (2) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 2.24 mm−1

  • T = 293 K

  • 0.39 × 0.29 × 0.20 mm
Data collection

  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.481, Tmax = 0.638

  • 12115 measured reflections

  • 2378 independent reflections

  • 2053 reflections with I > 2σ(I)

  • Rint = 0.035
Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.114

  • S = 1.06

  • 2378 reflections

  • 204 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—HN1⋯O2i 0.80 (3) 2.14 (3) 2.927 (3) 167
C13—H13⋯O2i 0.93 2.59 3.333 (3) 137
C3—H3⋯O4ii 0.93 2.58 3.459 (3) 155
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 978140

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814001317/hb7184sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814001317/hb7184Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814001317/hb7184Isup3.cml

checkCIF report


Introduction top

As a part of our continued efforts to study the crystal structures of N-(aroyl)-aryl­sulfonamides (Suchetan et al., 2010, 2011, 2012), we report here the crystal structure of the title compound (I) (Fig 1).

Experimental top

Synthesis and crystallization top

The title compound (I) was prepared by refluxing a mixture of 3-nitro­benzoic acid, 4-methyl­benzene­sulfonamide and phospho­rous oxychloride (POCl3) for 2 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The compound obtained was filtered and later dried (Melting point: 459 K).

Colorless prisms of (I) were obtained from a slow evaporation of its aqueous methano­lic solution at room temperature.

Refinement top

The H atom of the NH group was located in a difference map and later refined freely. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93-0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the Ueq of the parent atom).

Results and discussion top

In I, the dihedral angle between the two aromatic rings is 86.29 (1)°. Compared to this, the dihedral angle is 79.4 (1)° in N-(4-methyl­phenyl­sulfonyl)-benzamide (II) (Suchetan et al., 2010), 89.8 (1)° in N-(4-methyl­phenyl­sulfonyl)-4-nitro­benzamide (III) (Suchetan et al., 2011) and 86.9 (2)° in N-(phenyl­sulfonyl)-3-nitro­benzamide (IV) (Suchetan et al., 2012). Thus, introducing a nitro group into the benzoyl ring results in an increase of the dihedral angle between the aromatic rings. The conformation between the N—H bond and the meta-NO2 group is anti in contrast to the syn conformation observed in IV (Suchetan et al., 2012). The molecule is twisted at the S atom, the dihedral angle between the planes defined by the S—N—C=O segment in the central chain and the sulfonyl benzene rings being 79.16 (1)°.

In the crystal structure, the molecules are connected into inversion dimers through N1—HN1···O2 hydrogen bonds (Table 1, Figure 2) and C13—H13···O2 inter­actions forming R22(8) and R22(14) ring motifs respectively. These dimers are further connected into C(12) chains through C3—H3···O4 inter­actions forming sheets (Figure 2).

Related literature top

For related structures see: Suchetan et al. (2010, 2011, 2012).

Structure description top

As a part of our continued efforts to study the crystal structures of N-(aroyl)-aryl­sulfonamides (Suchetan et al., 2010, 2011, 2012), we report here the crystal structure of the title compound (I) (Fig 1).

In I, the dihedral angle between the two aromatic rings is 86.29 (1)°. Compared to this, the dihedral angle is 79.4 (1)° in N-(4-methyl­phenyl­sulfonyl)-benzamide (II) (Suchetan et al., 2010), 89.8 (1)° in N-(4-methyl­phenyl­sulfonyl)-4-nitro­benzamide (III) (Suchetan et al., 2011) and 86.9 (2)° in N-(phenyl­sulfonyl)-3-nitro­benzamide (IV) (Suchetan et al., 2012). Thus, introducing a nitro group into the benzoyl ring results in an increase of the dihedral angle between the aromatic rings. The conformation between the N—H bond and the meta-NO2 group is anti in contrast to the syn conformation observed in IV (Suchetan et al., 2012). The molecule is twisted at the S atom, the dihedral angle between the planes defined by the S—N—C=O segment in the central chain and the sulfonyl benzene rings being 79.16 (1)°.

In the crystal structure, the molecules are connected into inversion dimers through N1—HN1···O2 hydrogen bonds (Table 1, Figure 2) and C13—H13···O2 inter­actions forming R22(8) and R22(14) ring motifs respectively. These dimers are further connected into C(12) chains through C3—H3···O4 inter­actions forming sheets (Figure 2).

For related structures see: Suchetan et al. (2010, 2011, 2012).

Synthesis and crystallization top

The title compound (I) was prepared by refluxing a mixture of 3-nitro­benzoic acid, 4-methyl­benzene­sulfonamide and phospho­rous oxychloride (POCl3) for 2 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The compound obtained was filtered and later dried (Melting point: 459 K).

Colorless prisms of (I) were obtained from a slow evaporation of its aqueous methano­lic solution at room temperature.

Refinement details top

The H atom of the NH group was located in a difference map and later refined freely. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93-0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the Ueq of the parent atom).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. Formation of sheets in the crystal structure.
N-(4-Methylphenylsulfonyl)-3-nitrobenzamide top
Crystal data top
C14H12N2O5SPrism
Mr = 320.32Dx = 1.473 Mg m−3
Monoclinic, P21/cMelting point: 459 K
Hall symbol: -P 2ybcCu Kα radiation, λ = 1.54178 Å
a = 4.9736 (5) ÅCell parameters from 1127 reflections
b = 23.245 (2) Åθ = 3.8–64.5°
c = 12.7197 (11) ŵ = 2.24 mm−1
β = 100.820 (4)°T = 293 K
V = 1444.4 (2) Å3Prism, colourless
Z = 40.39 × 0.29 × 0.20 mm
F(000) = 664
Data collection top
Bruker APEXII
diffractometer		2053 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 64.5°, θmin = 3.8°
phi and φ scansh = −5→4
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −26→26
Tmin = 0.481, Tmax = 0.638l = −14→14
12115 measured reflections2 standard reflections every 1 reflections
2378 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0621P)2 + 0.3691P]
where P = (Fo2 + 2Fc2)/3
2378 reflections(Δ/σ)max < 0.001
204 parametersΔρmax = 0.20 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
Crystal data top
C14H12N2O5SV = 1444.4 (2) Å3
Mr = 320.32Z = 4
Monoclinic, P21/cCu Kα radiation
a = 4.9736 (5) ŵ = 2.24 mm−1
b = 23.245 (2) ÅT = 293 K
c = 12.7197 (11) Å0.39 × 0.29 × 0.20 mm
β = 100.820 (4)°
Data collection top
Bruker APEXII
diffractometer		2053 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		Rint = 0.035
Tmin = 0.481, Tmax = 0.6382 standard reflections every 1 reflections
12115 measured reflections intensity decay: 1%
2378 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.20 e Å−3
2378 reflectionsΔρmin = −0.23 e Å−3
204 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
xyzUiso*/Ueq
S11.10155 (10)0.50190 (2)0.32699 (4)0.0546 (2)
C80.6073 (4)0.63811 (8)0.33442 (15)0.0481 (5)
C90.4226 (4)0.66836 (8)0.25927 (16)0.0481 (5)
H90.41080.66150.18650.058*
O21.1994 (3)0.47252 (7)0.42557 (13)0.0667 (4)
N20.0629 (4)0.74082 (8)0.21424 (15)0.0570 (4)
O11.2908 (3)0.52526 (7)0.26821 (15)0.0720 (5)
N10.9164 (4)0.55519 (7)0.36288 (16)0.0534 (4)
C100.2572 (4)0.70859 (8)0.29425 (15)0.0471 (5)
O30.8066 (3)0.59550 (7)0.19878 (13)0.0695 (5)
O4−0.1159 (4)0.76822 (9)0.24399 (15)0.0891 (6)
O50.0900 (4)0.73809 (9)0.12131 (13)0.0853 (6)
C40.4935 (5)0.38740 (9)0.11605 (18)0.0593 (5)
C30.5450 (5)0.38158 (10)0.22531 (18)0.0646 (6)
H30.45080.35370.25630.077*
C70.7819 (4)0.59512 (9)0.29113 (17)0.0518 (5)
C50.6344 (5)0.42936 (10)0.07092 (18)0.0680 (6)
H50.60140.4341−0.00300.082*
C110.2669 (5)0.71991 (9)0.40117 (17)0.0583 (5)
H110.14940.74670.42290.070*
C10.8710 (4)0.45716 (8)0.24416 (16)0.0490 (5)
C60.8239 (5)0.46431 (10)0.13467 (19)0.0630 (6)
H60.91820.49230.10390.076*
C130.6243 (5)0.64965 (9)0.44227 (17)0.0602 (6)
H130.75000.62980.49280.072*
C20.7316 (5)0.41580 (10)0.29029 (17)0.0588 (5)
H20.76350.41110.36420.071*
C120.4558 (5)0.69042 (10)0.47530 (18)0.0669 (6)
H120.46960.69810.54790.080*
C140.2854 (6)0.34997 (12)0.0463 (2)0.0845 (8)
H14A0.18140.32920.09030.127*
H14B0.37760.32320.00780.127*
H14C0.16470.3736−0.00350.127*
HN10.860 (5)0.5495 (10)0.417 (2)0.062 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0368 (3)0.0518 (3)0.0732 (4)0.0021 (2)0.0053 (2)−0.0047 (2)
C80.0445 (11)0.0416 (10)0.0566 (11)−0.0023 (8)0.0052 (9)−0.0015 (8)
C90.0469 (11)0.0478 (11)0.0488 (10)−0.0051 (9)0.0071 (8)−0.0001 (8)
O20.0538 (9)0.0660 (10)0.0726 (10)0.0159 (7)−0.0079 (7)−0.0034 (8)
N20.0582 (11)0.0534 (10)0.0563 (11)0.0032 (9)0.0024 (8)0.0041 (8)
O10.0428 (8)0.0662 (10)0.1106 (13)−0.0065 (7)0.0238 (8)−0.0066 (9)
N10.0444 (10)0.0513 (10)0.0627 (11)0.0046 (8)0.0053 (8)−0.0017 (8)
C100.0458 (11)0.0423 (10)0.0508 (11)−0.0017 (8)0.0027 (8)0.0028 (8)
O30.0759 (11)0.0679 (10)0.0705 (11)0.0121 (8)0.0292 (8)0.0079 (8)
O40.0871 (13)0.0949 (14)0.0821 (12)0.0449 (11)0.0077 (10)0.0063 (10)
O50.0957 (14)0.1043 (14)0.0529 (10)0.0235 (11)0.0063 (9)0.0148 (9)
C40.0611 (13)0.0514 (12)0.0619 (13)0.0011 (10)0.0025 (10)−0.0020 (10)
C30.0647 (14)0.0599 (13)0.0669 (14)−0.0144 (11)0.0066 (11)0.0075 (11)
C70.0448 (11)0.0488 (11)0.0612 (13)−0.0026 (9)0.0084 (9)−0.0004 (9)
C50.0866 (17)0.0651 (14)0.0516 (12)−0.0038 (12)0.0111 (11)−0.0008 (10)
C110.0665 (14)0.0519 (11)0.0551 (12)0.0116 (10)0.0082 (10)−0.0036 (9)
C10.0414 (11)0.0471 (10)0.0587 (12)0.0034 (8)0.0100 (8)−0.0014 (9)
C60.0686 (15)0.0589 (13)0.0647 (13)−0.0080 (11)0.0207 (11)0.0028 (10)
C130.0670 (14)0.0536 (12)0.0540 (12)0.0093 (10)−0.0041 (10)0.0001 (9)
C20.0591 (13)0.0605 (13)0.0546 (12)−0.0081 (10)0.0054 (10)0.0051 (10)
C120.0871 (17)0.0623 (14)0.0471 (11)0.0166 (12)0.0017 (11)−0.0057 (10)
C140.096 (2)0.0701 (16)0.0780 (17)−0.0173 (14)−0.0082 (14)−0.0066 (13)
Geometric parameters (Å, º) top
S1—O11.4156 (17)C4—C141.507 (3)
S1—O21.4305 (16)C3—C21.375 (3)
S1—N11.6580 (18)C3—H30.9300
S1—C11.747 (2)C5—C61.385 (3)
C8—C131.385 (3)C5—H50.9300
C8—C91.386 (3)C11—C121.382 (3)
C8—C71.495 (3)C11—H110.9300
C9—C101.373 (3)C1—C61.378 (3)
C9—H90.9300C1—C21.379 (3)
N2—O41.211 (2)C6—H60.9300
N2—O51.216 (2)C13—C121.382 (3)
N2—C101.470 (3)C13—H130.9300
N1—C71.383 (3)C2—H20.9300
N1—HN10.80 (2)C12—H120.9300
C10—C111.377 (3)C14—H14A0.9600
O3—C71.204 (3)C14—H14B0.9600
C4—C31.372 (3)C14—H14C0.9600
C4—C51.387 (3)
O1—S1—O2119.71 (11)N1—C7—C8116.62 (19)
O1—S1—N1108.51 (10)C6—C5—C4120.8 (2)
O2—S1—N1103.33 (10)C6—C5—H5119.6
O1—S1—C1109.63 (10)C4—C5—H5119.6
O2—S1—C1108.74 (10)C10—C11—C12118.2 (2)
N1—S1—C1105.96 (9)C10—C11—H11120.9
C13—C8—C9119.62 (18)C12—C11—H11120.9
C13—C8—C7124.23 (18)C6—C1—C2120.7 (2)
C9—C8—C7116.14 (18)C6—C1—S1120.36 (16)
C10—C9—C8118.78 (18)C2—C1—S1118.94 (16)
C10—C9—H9120.6C1—C6—C5119.3 (2)
C8—C9—H9120.6C1—C6—H6120.4
O4—N2—O5123.57 (19)C5—C6—H6120.4
O4—N2—C10118.53 (19)C12—C13—C8120.42 (19)
O5—N2—C10117.89 (18)C12—C13—H13119.8
C7—N1—S1123.00 (17)C8—C13—H13119.8
C7—N1—HN1118.4 (18)C3—C2—C1119.0 (2)
S1—N1—HN1114.5 (17)C3—C2—H2120.5
C9—C10—C11122.56 (18)C1—C2—H2120.5
C9—C10—N2118.58 (17)C11—C12—C13120.4 (2)
C11—C10—N2118.86 (18)C11—C12—H12119.8
C3—C4—C5118.4 (2)C13—C12—H12119.8
C3—C4—C14121.1 (2)C4—C14—H14A109.5
C5—C4—C14120.5 (2)C4—C14—H14B109.5
C4—C3—C2121.9 (2)H14A—C14—H14B109.5
C4—C3—H3119.0C4—C14—H14C109.5
C2—C3—H3119.0H14A—C14—H14C109.5
O3—C7—N1121.6 (2)H14B—C14—H14C109.5
O3—C7—C8121.82 (19)
C13—C8—C9—C10−1.0 (3)C14—C4—C5—C6179.3 (2)
C7—C8—C9—C10−179.78 (17)C9—C10—C11—C121.7 (3)
O1—S1—N1—C751.79 (19)N2—C10—C11—C12−178.2 (2)
O2—S1—N1—C7179.85 (17)O1—S1—C1—C6−23.4 (2)
C1—S1—N1—C7−65.87 (19)O2—S1—C1—C6−155.95 (17)
C8—C9—C10—C11−0.3 (3)N1—S1—C1—C693.55 (19)
C8—C9—C10—N2179.61 (17)O1—S1—C1—C2158.45 (17)
O4—N2—C10—C9166.6 (2)O2—S1—C1—C225.9 (2)
O5—N2—C10—C9−12.9 (3)N1—S1—C1—C2−84.63 (19)
O4—N2—C10—C11−13.5 (3)C2—C1—C6—C5−0.1 (3)
O5—N2—C10—C11167.0 (2)S1—C1—C6—C5−178.20 (18)
C5—C4—C3—C2−0.3 (4)C4—C5—C6—C1−0.2 (4)
C14—C4—C3—C2−179.2 (2)C9—C8—C13—C121.0 (3)
S1—N1—C7—O3−4.9 (3)C7—C8—C13—C12179.6 (2)
S1—N1—C7—C8175.83 (14)C4—C3—C2—C10.0 (4)
C13—C8—C7—O3−162.5 (2)C6—C1—C2—C30.2 (3)
C9—C8—C7—O316.1 (3)S1—C1—C2—C3178.32 (18)
C13—C8—C7—N116.8 (3)C10—C11—C12—C13−1.7 (4)
C9—C8—C7—N1−164.58 (18)C8—C13—C12—C110.4 (4)
C3—C4—C5—C60.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—HN1···O2i0.80 (3)2.14 (3)2.927 (3)167
C13—H13···O2i0.932.593.333 (3)137
C3—H3···O4ii0.932.583.459 (3)155
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—HN1···O2i0.80 (3)2.14 (3)2.927 (3)167
C13—H13···O2i0.932.593.333 (3)137
C3—H3···O4ii0.932.583.459 (3)155
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x, y−1/2, −z+1/2.
 

Acknowledgements

The authors acknowledge the IOE X-ray diffractometer facility, University of Mysore, Mysore, for the data collection.

References

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ISSN: 2056-9890
Volume 70| Part 2| February 2014| Page o191
doi:10.1107/S1600536814001317
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