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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 68| Part 10| October 2012| Page o3028
https://doi.org/10.1107/S1600536812037701

4-Meth­­oxy-N-(4-meth­­oxy-2-nitro­phen­yl)benzamide

Muhammad Arshad,a Sammer Yousuf,a,b* Sumayya Saeedb and Fatima Z. Bashaa‡

aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and bDepartment of Chemistry, University of Karachi, Karachi 75270, Pakistan
*Correspondence e-mail: dr.sammer.yousuf@gmail.com

(Received 27 August 2012; accepted 2 September 2012; online 29 September 2012)

In the title compound, C15H14N2O5, the central amide C—C(=O)—N—C unit forms dihedral angles of 28.17 (13) and 26.47 (13)° with the two benzene rings, whereas the two benzene rings are almost coplanar, making a dihedral angle of 4.52 (13)°. The two meth­oxy and the nitro substituents are almost coplanar with their attached benzene rings, with C—O—C—C torsion angles of −1.3 (4) and −4.6 (4)°, and an O—N—C—C torsion angle of 17.1 (3)°. In the crystal, mol­ecules are linked via C—H⋯O and N—H⋯O inter­actions, forming a tape running along the b axis.

Related literature

For the crystal structures of related benzamide compounds, see: Sripet et al. (2012[Sripet, W., Chantrapromma, S., Ruanwas, P. & Fun, H.-K. (2012). Acta Cryst. E68, o1234.]); Saeed et al. (2008[Saeed, A., Khera, R. A., Batool, M., Shaheen, U. & Flörke, U. (2008). Acta Cryst. E64, o1625.]); Saeed & Flörke (2009[Saeed, A. & Flörke, U. (2009). Acta Cryst. E65, o1948.]).

[Scheme 1]

Experimental

Crystal data

  • C15H14N2O5

  • Mr = 302.28

  • Monoclinic, P 21 /n

  • a = 9.7206 (12) Å

  • b = 4.9885 (6) Å

  • c = 28.725 (4) Å

  • β = 95.628 (2)°

  • V = 1386.2 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 273 K

  • 0.30 × 0.12 × 0.07 mm
Data collection

  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.968, Tmax = 0.992

  • 7491 measured reflections

  • 2552 independent reflections

  • 1638 reflections with I > 2σ(I)

  • Rint = 0.049
Refinement

  • R[F2 > 2σ(F2)] = 0.064

  • wR(F2) = 0.155

  • S = 1.00

  • 2552 reflections

  • 205 parameters

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

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O2i 0.80 (3) 2.34 (3) 3.027 (3) 145 (3)
C10—H10A⋯O5ii 0.93 2.45 3.364 (3) 168
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+2, -z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812037701/is5189sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037701/is5189Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812037701/is5189Isup3.cml

checkCIF report


Comment top

The formation of amide functionality is a fundamental reaction and of great interest in organic chemistry. Due to a number of application in industrial and pharmaceutical areas as well as an important intermediate in synthetic chemistry, it remains a great challenge for the chemists to develop an efficient method for the synthesis of amides. The title compound was obtained during our attempt to synthesize libraries of benzamide derivatives under different conditions.

The molecule of title compound is not planner. The central amide unit (C6/C7/O2/N1/C8) forms dihedral angles of 28.17 (13) and 26.47 (13)°, respectively, with benzene C1–C6 and C8–C13 rings. The dihedral angle between the two C1–C6 and C8–C13 rings is 4.52 (13)°. The two methoxy and the nitro susbtituents lie nearly in plane of the corresponding aromatic rings with torsion angles C14—O3—C11—C12 of -4.6 (4)°, C15—O1—C3—C2 of -1.3 (4)°, O5—N2—C9—C10 of 17.1 (4)° and O4—N2—C9—C10 of -161.3 (3)°. The bond lengths and angles are similar to those found in the related benzamide derivatives (Sripet et al., 2012; Saeed et al., 2008; Saeed & Flörke, 2009). In the crystal, molecules are linked via intermolecular C—H···O and N—H···O (symmetry codes as in Table 2) interactions to form an infinite tape structure running along the b axis (Fig. 2).

Related literature top

For the crystal structures of related benzamide compounds, see: Sripet et al. (2012); Saeed et al. (2008); Saeed & Flörke (2009).

Experimental top

The title compound was synthesized by using the following procedure. To the stirring solution of 4-methoxy-2-nitroaniline (2.97 mmol) in 6.5 ml dichloromethane, p-methoxybenzoyl chloride (8.12 mmol) and triethylamine (0.5 ml) were added carefully at room temperature. The progress of reaction was checked by TLC and was completed in 12 h. Then the reaction mixture was diluted with water (25 ml) and acidified with 1.0 M HCl (50 ml). The organic compound was extracted with ethyl acetate (2×25 mL) and washed with brine (50 ml). The organic layer was dried (anhyd. MgSO4), filtered and concentrated on rotavapor. The crude mixture was purified by silica gel column chromatography by using ethyl acetate and hexane to get title compound with 77% yield. After column chromatography, the pure compound was left overnight. The crystals obtained were found suitable for single-crystal X-ray diffraction studies. All chemicals were purchased from Sigma-Aldrich and Alfa Aesar.

Refinement top

The H atom on the nitrogen was located in a difference Fourier maps and refined freely [N—H = 0.80 (3) Å]. Other H atoms were positioned geometrically with 0.93 or 0.96 Å and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). A rotating group model was applied to the methyl groups.

Structure description top

The formation of amide functionality is a fundamental reaction and of great interest in organic chemistry. Due to a number of application in industrial and pharmaceutical areas as well as an important intermediate in synthetic chemistry, it remains a great challenge for the chemists to develop an efficient method for the synthesis of amides. The title compound was obtained during our attempt to synthesize libraries of benzamide derivatives under different conditions.

The molecule of title compound is not planner. The central amide unit (C6/C7/O2/N1/C8) forms dihedral angles of 28.17 (13) and 26.47 (13)°, respectively, with benzene C1–C6 and C8–C13 rings. The dihedral angle between the two C1–C6 and C8–C13 rings is 4.52 (13)°. The two methoxy and the nitro susbtituents lie nearly in plane of the corresponding aromatic rings with torsion angles C14—O3—C11—C12 of -4.6 (4)°, C15—O1—C3—C2 of -1.3 (4)°, O5—N2—C9—C10 of 17.1 (4)° and O4—N2—C9—C10 of -161.3 (3)°. The bond lengths and angles are similar to those found in the related benzamide derivatives (Sripet et al., 2012; Saeed et al., 2008; Saeed & Flörke, 2009). In the crystal, molecules are linked via intermolecular C—H···O and N—H···O (symmetry codes as in Table 2) interactions to form an infinite tape structure running along the b axis (Fig. 2).

For the crystal structures of related benzamide compounds, see: Sripet et al. (2012); Saeed et al. (2008); Saeed & Flörke (2009).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound. Hydrogen atoms are omitted for clearity. Dashed lines indicate the C—H···O and N—H···O hydrogen bonds.
4-Methoxy-N-(4-methoxy-2-nitrophenyl)benzamide top
Crystal data top
C15H14N2O5F(000) = 632
Mr = 302.28Dx = 1.448 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ynCell parameters from 1456 reflections
a = 9.7206 (12) Åθ = 2.3–28.0°
b = 4.9885 (6) ŵ = 0.11 mm−1
c = 28.725 (4) ÅT = 273 K
β = 95.628 (2)°Plate, colorles
V = 1386.2 (3) Å30.30 × 0.12 × 0.07 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2552 independent reflections
Radiation source: fine-focus sealed tube1638 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ω scanθmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −9→11
Tmin = 0.968, Tmax = 0.992k = −6→6
7491 measured reflectionsl = −34→34
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0824P)2]
where P = (Fo2 + 2Fc2)/3
2552 reflections(Δ/σ)max < 0.001
205 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C15H14N2O5V = 1386.2 (3) Å3
Mr = 302.28Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.7206 (12) ŵ = 0.11 mm−1
b = 4.9885 (6) ÅT = 273 K
c = 28.725 (4) Å0.30 × 0.12 × 0.07 mm
β = 95.628 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2552 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		1638 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.992Rint = 0.049
7491 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.155H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.24 e Å−3
2552 reflectionsΔρmin = −0.19 e Å−3
205 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
xyzUiso*/Ueq
O1−0.0633 (2)0.6081 (4)0.30064 (6)0.0569 (6)
O20.0516 (2)0.0858 (3)0.10748 (7)0.0621 (7)
O30.3257 (2)0.4247 (4)−0.08001 (6)0.0560 (6)
O40.3544 (2)0.8107 (5)0.11160 (7)0.0759 (8)
O50.4308 (2)1.0026 (4)0.05315 (7)0.0629 (7)
N10.1306 (2)0.5046 (4)0.09575 (8)0.0413 (6)
N20.3622 (2)0.8309 (4)0.06979 (8)0.0415 (6)
C10.1170 (3)0.6004 (5)0.19444 (9)0.0431 (7)
H1B0.18890.68720.18150.052*
C20.0863 (3)0.6723 (5)0.23865 (9)0.0465 (7)
H2A0.13830.80330.25540.056*
C3−0.0216 (3)0.5495 (5)0.25793 (9)0.0415 (7)
C4−0.0970 (3)0.3527 (6)0.23291 (9)0.0508 (8)
H4A−0.17090.27080.24560.061*
C5−0.0633 (3)0.2782 (5)0.18956 (9)0.0488 (8)
H5A−0.11300.14150.17360.059*
C60.0434 (3)0.4016 (4)0.16870 (8)0.0361 (6)
C70.0754 (3)0.3157 (4)0.12181 (8)0.0368 (6)
C80.1817 (3)0.4747 (4)0.05195 (8)0.0340 (6)
C90.2883 (3)0.6356 (4)0.03780 (8)0.0329 (6)
C100.3324 (3)0.6180 (5)−0.00614 (8)0.0381 (7)
H10A0.40170.7313−0.01460.046*
C110.2736 (3)0.4317 (5)−0.03782 (8)0.0386 (7)
C120.1694 (3)0.2690 (5)−0.02481 (9)0.0404 (7)
H12A0.12970.1416−0.04560.048*
C130.1236 (3)0.2943 (5)0.01899 (9)0.0413 (7)
H13A0.05110.18640.02660.050*
C140.2750 (3)0.2204 (6)−0.11201 (9)0.0567 (8)
H14A0.32270.2301−0.13970.085*
H14B0.17780.2458−0.12020.085*
H14C0.29050.0479−0.09760.085*
C150.0108 (4)0.8074 (6)0.32821 (9)0.0627 (9)
H15A−0.02760.82460.35760.094*
H15B0.00370.97580.31200.094*
H15C0.10620.75630.33360.094*
H1A0.138 (3)0.648 (6)0.1083 (9)0.059 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0677 (16)0.0606 (12)0.0453 (11)−0.0009 (11)0.0196 (10)−0.0054 (10)
O20.1059 (19)0.0283 (9)0.0559 (12)−0.0171 (10)0.0273 (11)−0.0071 (9)
O30.0702 (16)0.0543 (11)0.0473 (11)−0.0215 (10)0.0250 (10)−0.0120 (9)
O40.085 (2)0.0929 (16)0.0514 (13)−0.0457 (14)0.0168 (11)−0.0209 (12)
O50.0706 (17)0.0463 (11)0.0716 (14)−0.0343 (11)0.0066 (11)0.0025 (10)
N10.0570 (18)0.0242 (11)0.0452 (13)−0.0096 (10)0.0184 (11)−0.0070 (10)
N20.0403 (16)0.0338 (11)0.0504 (14)−0.0078 (10)0.0051 (11)−0.0041 (11)
C10.0422 (19)0.0399 (14)0.0492 (16)−0.0091 (13)0.0147 (13)−0.0034 (13)
C20.056 (2)0.0392 (14)0.0449 (15)−0.0088 (13)0.0094 (14)−0.0082 (13)
C30.046 (2)0.0384 (14)0.0413 (15)0.0061 (13)0.0110 (13)0.0037 (12)
C40.049 (2)0.0525 (16)0.0533 (17)−0.0147 (14)0.0177 (14)0.0016 (14)
C50.057 (2)0.0408 (14)0.0493 (16)−0.0179 (14)0.0113 (14)−0.0033 (13)
C60.0405 (18)0.0255 (11)0.0432 (14)−0.0013 (11)0.0083 (12)0.0005 (11)
C70.0398 (18)0.0256 (12)0.0457 (14)−0.0004 (11)0.0085 (12)−0.0031 (11)
C80.0384 (18)0.0248 (11)0.0400 (14)−0.0019 (11)0.0110 (12)0.0002 (10)
C90.0321 (17)0.0226 (11)0.0438 (14)−0.0023 (10)0.0026 (12)−0.0019 (10)
C100.0377 (18)0.0307 (12)0.0477 (15)−0.0057 (12)0.0126 (12)0.0034 (11)
C110.0444 (19)0.0325 (12)0.0405 (14)0.0013 (12)0.0122 (12)−0.0002 (11)
C120.0469 (19)0.0299 (12)0.0454 (15)−0.0085 (12)0.0100 (13)−0.0080 (11)
C130.0434 (19)0.0334 (12)0.0488 (15)−0.0147 (12)0.0127 (13)−0.0068 (12)
C140.068 (2)0.0585 (18)0.0457 (16)−0.0103 (16)0.0147 (15)−0.0122 (14)
C150.097 (3)0.0487 (16)0.0445 (16)0.0080 (17)0.0159 (17)−0.0035 (14)
Geometric parameters (Å, º) top
O1—C31.361 (3)C5—C61.391 (4)
O1—C151.422 (3)C5—H5A0.9300
O2—C71.232 (3)C6—C71.475 (3)
O3—C111.359 (3)C8—C131.386 (3)
O3—C141.427 (3)C8—C91.402 (3)
O4—N21.215 (3)C9—C101.375 (3)
O5—N21.212 (3)C10—C111.384 (3)
N1—C71.348 (3)C10—H10A0.9300
N1—C81.405 (3)C11—C121.378 (4)
N1—H1A0.80 (3)C12—C131.381 (3)
N2—C91.476 (3)C12—H12A0.9300
C1—C21.380 (3)C13—H13A0.9300
C1—C61.392 (3)C14—H14A0.9600
C1—H1B0.9300C14—H14B0.9600
C2—C31.377 (4)C14—H14C0.9600
C2—H2A0.9300C15—H15A0.9600
C3—C41.384 (4)C15—H15B0.9600
C4—C51.370 (4)C15—H15C0.9600
C4—H4A0.9300
C3—O1—C15118.2 (2)C13—C8—N1121.6 (2)
C11—O3—C14117.2 (2)C9—C8—N1122.3 (2)
C7—N1—C8128.2 (2)C10—C9—C8122.4 (2)
C7—N1—H1A113 (2)C10—C9—N2116.0 (2)
C8—N1—H1A118 (2)C8—C9—N2121.7 (2)
O5—N2—O4122.6 (2)C9—C10—C11120.1 (2)
O5—N2—C9118.2 (2)C9—C10—H10A120.0
O4—N2—C9119.2 (2)C11—C10—H10A120.0
C2—C1—C6121.8 (3)O3—C11—C12125.1 (2)
C2—C1—H1B119.1O3—C11—C10116.0 (2)
C6—C1—H1B119.1C12—C11—C10118.9 (2)
C3—C2—C1119.8 (2)C11—C12—C13120.3 (2)
C3—C2—H2A120.1C11—C12—H12A119.9
C1—C2—H2A120.1C13—C12—H12A119.9
O1—C3—C2125.0 (2)C12—C13—C8122.4 (2)
O1—C3—C4115.5 (3)C12—C13—H13A118.8
C2—C3—C4119.5 (2)C8—C13—H13A118.8
C5—C4—C3120.2 (3)O3—C14—H14A109.5
C5—C4—H4A119.9O3—C14—H14B109.5
C3—C4—H4A119.9H14A—C14—H14B109.5
C4—C5—C6121.8 (2)O3—C14—H14C109.5
C4—C5—H5A119.1H14A—C14—H14C109.5
C6—C5—H5A119.1H14B—C14—H14C109.5
C5—C6—C1116.9 (2)O1—C15—H15A109.5
C5—C6—C7119.8 (2)O1—C15—H15B109.5
C1—C6—C7123.3 (2)H15A—C15—H15B109.5
O2—C7—N1122.5 (2)O1—C15—H15C109.5
O2—C7—C6121.7 (2)H15A—C15—H15C109.5
N1—C7—C6115.8 (2)H15B—C15—H15C109.5
C13—C8—C9115.9 (2)
C6—C1—C2—C3−1.3 (4)C13—C8—C9—C100.4 (4)
C15—O1—C3—C2−1.3 (4)N1—C8—C9—C10−175.8 (2)
C15—O1—C3—C4179.6 (2)C13—C8—C9—N2−178.2 (2)
C1—C2—C3—O1−178.4 (2)N1—C8—C9—N25.6 (4)
C1—C2—C3—C40.7 (4)O5—N2—C9—C1017.1 (3)
O1—C3—C4—C5−179.8 (2)O4—N2—C9—C10−161.4 (2)
C2—C3—C4—C50.9 (4)O5—N2—C9—C8−164.2 (2)
C3—C4—C5—C6−2.1 (4)O4—N2—C9—C817.4 (4)
C4—C5—C6—C11.6 (4)C8—C9—C10—C11−1.7 (4)
C4—C5—C6—C7−179.6 (2)N2—C9—C10—C11177.0 (2)
C2—C1—C6—C50.2 (4)C14—O3—C11—C12−4.6 (4)
C2—C1—C6—C7−178.6 (2)C14—O3—C11—C10175.1 (2)
C8—N1—C7—O2−6.6 (4)C9—C10—C11—O3−178.6 (2)
C8—N1—C7—C6174.1 (2)C9—C10—C11—C121.1 (4)
C5—C6—C7—O2−27.8 (4)O3—C11—C12—C13−179.6 (2)
C1—C6—C7—O2150.9 (3)C10—C11—C12—C130.7 (4)
C5—C6—C7—N1151.5 (3)C11—C12—C13—C8−2.1 (4)
C1—C6—C7—N1−29.7 (4)C9—C8—C13—C121.5 (4)
C7—N1—C8—C1333.7 (4)N1—C8—C13—C12177.7 (2)
C7—N1—C8—C9−150.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.80 (3)2.34 (3)3.027 (3)145 (3)
C10—H10A···O5ii0.932.453.364 (3)168
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formulaC15H14N2O5
Mr302.28
Crystal system, space groupMonoclinic, P21/n
Temperature (K)273
a, b, c (Å)9.7206 (12), 4.9885 (6), 28.725 (4)
β (°) 95.628 (2)
V (Å3)1386.2 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.30 × 0.12 × 0.07
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.968, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections		7491, 2552, 1638
Rint0.049
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.155, 1.00
No. of reflections2552
No. of parameters205
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.24, −0.19

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.80 (3)2.34 (3)3.027 (3)145 (3)
C10—H10A···O5ii0.932.453.364 (3)168
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+2, −z.
 

Footnotes

‡Additional corresponding author, e-mail: bashafz@gmail.com.

References

First citationBruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationNardelli, M. (1995). J. Appl. Cryst. 28, 659.  CrossRef IUCr Journals Google Scholar
 First citationSaeed, A. & Flörke, U. (2009). Acta Cryst. E65, o1948.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSaeed, A., Khera, R. A., Batool, M., Shaheen, U. & Flörke, U. (2008). Acta Cryst. E64, o1625.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSripet, W., Chantrapromma, S., Ruanwas, P. & Fun, H.-K. (2012). Acta Cryst. E68, o1234.  CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o3028
https://doi.org/10.1107/S1600536812037701
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