2-Methyl-3-(4-nitro­phen­yl)acrylic acid

Muhammad, N.; Tahir, M.N.; Zia-ur-Rehman; Ali, S.

doi:10.1107/S1600536808024999

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages o1717-o1718

doi:10.1107/S1600536808024999

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2-Methyl-3-(4-nitrophenyl)acrylic acid

Niaz Muhammad,^a M. Nawaz Tahir,^b ^* Zia-ur-Rehman ^a and Saqib Ali ^a

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 10 July 2008; accepted 3 August 2008; online 6 August 2008)

The title compound, C₁₀H₉NO₄, forms R₂²(8) dimers due to intermolecular O—H⋯O hydrogen bonding in the crystal structure. Two dimers are further linked to each other through two intermolecular C—H⋯O hydrogen bonds, forming an R₃³(7) ring motif. The nitro groups form an intramolecular C—H⋯O hydrogen bond mimicking a five-membered ring. As a result of these hydrogen bonds, polymeric sheets are formed. The aromatic ring makes a dihedral angle of 42.84 (8)° with the carboxylate group and an angle of 8.01 (14)° with the nitro group. There is a π-interaction (N—O⋯π) between the nitro group and the aromatic ring, with a distance of 3.7572 (14) Å between the N atom and the centroid of the aromatic ring.

Related literature

For related literature, see: Bernstein et al. (1995 ); Fujii et al. (2002 ); Ma & Hayes (2004 ); Muhammad et al. (2007 , 2008a ,b ); Muhammad, Ali, Tahir & Zia-ur-Rehman (2008 ); Muhammad, Tahir, Ali, Zia-ur-Rehman & Kashmiri (2008 ); Muhammad, Tahir, Zia-ur-Rehman & Ali (2008 ); Muhammad, Tahir, Zia-ur-Rehman, Ali & Shaheen, 2008 ); Niaz et al. (2008 ).

Experimental

Crystal data

C₁₀H₉NO₄
M_r = 207.18
Triclinic, $[P \overline 1]$
a = 7.3878 (3) Å
b = 8.1050 (5) Å
c = 8.3402 (4) Å
α = 75.793 (2)°
β = 81.835 (3)°
γ = 87.686 (2)°
V = 479.21 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 (2) K
0.25 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.970, T_max = 0.981
9039 measured reflections
2518 independent reflections
1926 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.134
S = 1.02
2518 reflections
140 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.93 (2)	1.71 (2)	2.6333 (15)	177 (2)
C3—H3⋯O1	0.93	2.31	2.7080 (17)	105
C8—H8⋯O1ⁱⁱ	0.93	2.55	3.3471 (17)	144
C9—H9⋯O2ⁱⁱⁱ	0.93	2.60	3.4912 (17)	161
Symmetry codes: (i) -x, -y, -z+1; (ii) x, y+1, z; (iii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2; 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: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024999/cs2087sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808024999/cs2087Isup2.hkl

checkCIF report

Comment top

Cinnamic acid derivatives are widely used chemicals in a variety of fields (Ma et al., 2004). They have been applied as antibacterial agents for suppression of bacterial growth (Fujii et al., 2002). In wine, cinnamic acid and its derivatives join benzoic acid derivatives and flavonoids in creating pigments and tannin agents that give each vintage its characteristic bouquet and color. The title compound has been prepared in continuation of synthesizing various derivatives of cinamic acids (Niaz et al., 2008; Muhammad, Ali, Tahir & Zia-ur-Rehman, 2008; Muhammad, Tahir, Ali, Zia-ur-Rehman & Kashmiri, 2008) and their tin complexes (Muhammad et al., 2008a,b).

The crystal structures of 3-(4-isopropylphenyl)-2-methylacrylic acid (Muhammad, Tahir, Ali, Zia-ur-Rehman & Kashmiri, 2008), of 3-(4-clorophenyl)-2-methylacrylic acid (Muhammad, Tahir, Zia-ur-Rehman, Ali & Shaheen, 2008) and of 3-(4-bromophenyl)-2-methylacrylic acid (Muhammad et al., 2007) have been reported. The title compound differs from these compounds due to the nitro group at para position. In the crystal structure of the title compound, the exocyclic C_sp2—C_sp2 bonds are of 1.4770 (18) and 1.4880 (18) Å, the C==C is of 1.3376 (18) Å. The C—O bond length 1.2996 (16) Å is normal, much like the C=O bond length of 1.2300 (15) Å. The resonant N—O bond lengths are equal (1.2185 (16) and 1.2204 (17) Å). There is an interamolecular H-bond of C—H···O type (Table 1, Fig 1). Centrosymmetric R₂²(8) dimers (Bernstein et al. 1995) are formed due to the intermolecular O1—H1···O2ⁱ [symmetry code: i = -x, -y, -z + 1] hydrogen bonding. Two adjacent dimers are linked to each other through two intermolecular H-bonds of C—H···O type forming an R₃³(7) motif (Bernstein et al. 1995). The group of two dimers are linked to each other by intermolcular H-bonding (Table 1, Fig 2). There exist an N1—O4···Cgⁱⁱ [symmetry code: ii = -x + 1, -y + 2, -z] interaction with a distance of 3.7572 (14) Å between the N-atom and the centroid of the (C4—C9) aromatic ring. The aromatic ring makes a dihedral angle of 42.84 (8)° with with the carboxylate (O1/C1/O2) moiety and 8.01 (14)° with the (N1/O3/O4) nitro group. Due to the intermolecular H-bonding polymeric sheets are formed.

Related literature top

For related literature, see: Bernstein et al. (1995); Fujii et al. (2002); Ma & Hayes (2004); Muhammad et al. (2007, 2008a,b); Muhammad, Ali, Tahir & Zia-ur-Rehman (2008); Muhammad, Tahir, Ali, Zia-ur-Rehman & Kashmiri (2008); Muhammad, Tahir, Zia-ur-Rehman & Ali (2008); Muhammad, Tahir, Zia-ur-Rehman, Ali & Shaheen, 2008); Niaz et al. (2008).

Experimental top

The title compound was prepared according to a reported procedure (Muhammad et al., 2007). A mixture of 4-nitrobenzaldehyde (1.51 g, 10 mmol), methylmalonic acid (2.36 g, 20 mmol) and piperidine (1.98 ml, 20 mmol) in a pyridine (12.5 ml) solution was heated on a steam-bath for 24 h. The reaction mixture was cooled and added to a mixture of 25 ml of concentrated HCl and 50 g of ice. The precipitate formed in the acidified mixture was filtered off and washed with ice-cold water. The product was recrystallized from ethanol. The yield was 79%.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

	Fig. 1. ORTEP drawing of the title compound, C₁₁H₁₂O₂ with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii. The intramolecular H-bonds are shown by dotted lines.
	Fig. 2. The packing figure (PLATON: Spek, 2003) which shows the dimeric nature of the compound and the interlinkages of the dimers.

2-Methyl-3-(4-nitrophenyl)acrylic acid top

Crystal data top

C₁₀H₉NO₄	Z = 2
M_r = 207.18	F(000) = 216
Triclinic, P1	D_x = 1.436 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3878 (3) Å	Cell parameters from 2518 reflections
b = 8.1050 (5) Å	θ = 2.5–29.1°
c = 8.3402 (4) Å	µ = 0.11 mm⁻¹
α = 75.793 (2)°	T = 296 K
β = 81.835 (3)°	Prismatic, colourless
γ = 87.686 (2)°	0.25 × 0.20 × 0.18 mm
V = 479.21 (4) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	2518 independent reflections
Radiation source: fine-focus sealed tube	1926 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 7.4 pixels mm^-1	θ_max = 29.1°, θ_min = 2.5°
ω scans	h = −10→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→9
T_min = 0.970, T_max = 0.981	l = −11→11
9039 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0713P)² + 0.0915P] where P = (F_o² + 2F_c²)/3
2518 reflections	(Δ/σ)_max < 0.001
140 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₀H₉NO₄	γ = 87.686 (2)°
M_r = 207.18	V = 479.21 (4) Å³
Triclinic, P1	Z = 2
a = 7.3878 (3) Å	Mo Kα radiation
b = 8.1050 (5) Å	µ = 0.11 mm⁻¹
c = 8.3402 (4) Å	T = 296 K
α = 75.793 (2)°	0.25 × 0.20 × 0.18 mm
β = 81.835 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2518 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1926 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.981	R_int = 0.023
9039 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.24 e Å⁻³
2518 reflections	Δρ_min = −0.21 e Å⁻³
140 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.04661 (16)	0.13519 (13)	0.29456 (12)	0.0547 (4)
O2	0.09796 (15)	0.16087 (12)	0.54300 (12)	0.0526 (3)
O3	0.52309 (18)	1.11600 (15)	−0.36244 (14)	0.0661 (4)
O4	0.35761 (19)	1.23296 (13)	−0.18699 (15)	0.0648 (4)
N1	0.41247 (18)	1.10856 (14)	−0.23745 (14)	0.0466 (4)
C1	0.10453 (16)	0.21896 (15)	0.39150 (15)	0.0357 (3)
C2	0.17797 (17)	0.39231 (15)	0.31101 (16)	0.0362 (3)
C3	0.17195 (18)	0.45348 (15)	0.14759 (16)	0.0378 (3)
C4	0.22936 (17)	0.62471 (15)	0.04743 (15)	0.0361 (3)
C5	0.3308 (2)	0.64219 (16)	−0.11015 (16)	0.0424 (4)
C6	0.39099 (19)	0.80039 (17)	−0.20464 (16)	0.0425 (4)
C7	0.34487 (18)	0.94026 (15)	−0.14089 (15)	0.0375 (4)
C8	0.2375 (2)	0.92912 (16)	0.01030 (17)	0.0432 (4)
C9	0.1804 (2)	0.76957 (16)	0.10462 (16)	0.0430 (4)
C10	0.2580 (2)	0.47901 (17)	0.42356 (17)	0.0480 (4)
H1	−0.005 (3)	0.032 (3)	0.355 (2)	0.0656*
H3	0.12727	0.38114	0.09157	0.0454*
H5	0.35821	0.54652	−0.15208	0.0508*
H6	0.46089	0.81202	−0.30868	0.0510*
H8	0.20402	1.02624	0.04821	0.0518*
H9	0.10844	0.75935	0.20750	0.0516*
H10A	0.33667	0.40104	0.48836	0.0719*
H10B	0.16126	0.51574	0.49695	0.0719*
H10C	0.32723	0.57588	0.35757	0.0719*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0855 (8)	0.0371 (5)	0.0397 (5)	−0.0259 (5)	−0.0071 (5)	−0.0026 (4)
O2	0.0801 (7)	0.0381 (5)	0.0357 (5)	−0.0229 (5)	−0.0058 (5)	0.0008 (4)
O3	0.0862 (8)	0.0524 (7)	0.0487 (6)	−0.0249 (6)	0.0068 (6)	0.0033 (5)
O4	0.1010 (9)	0.0290 (5)	0.0614 (7)	−0.0085 (5)	−0.0120 (6)	−0.0036 (5)
N1	0.0638 (7)	0.0340 (6)	0.0385 (6)	−0.0119 (5)	−0.0133 (5)	0.0030 (5)
C1	0.0399 (6)	0.0288 (6)	0.0353 (6)	−0.0057 (5)	−0.0021 (5)	−0.0028 (4)
C2	0.0379 (6)	0.0278 (5)	0.0392 (6)	−0.0052 (5)	−0.0024 (5)	−0.0019 (5)
C3	0.0443 (6)	0.0284 (6)	0.0380 (6)	−0.0068 (5)	−0.0037 (5)	−0.0029 (5)
C4	0.0416 (6)	0.0294 (6)	0.0342 (6)	−0.0041 (5)	−0.0064 (5)	−0.0004 (4)
C5	0.0569 (8)	0.0300 (6)	0.0375 (6)	−0.0005 (5)	−0.0009 (5)	−0.0062 (5)
C6	0.0521 (7)	0.0360 (6)	0.0338 (6)	−0.0020 (5)	0.0023 (5)	−0.0023 (5)
C7	0.0468 (7)	0.0281 (6)	0.0343 (6)	−0.0062 (5)	−0.0093 (5)	0.0017 (5)
C8	0.0607 (8)	0.0292 (6)	0.0380 (6)	0.0016 (5)	−0.0052 (6)	−0.0062 (5)
C9	0.0554 (8)	0.0348 (6)	0.0334 (6)	−0.0009 (5)	0.0030 (5)	−0.0029 (5)
C10	0.0626 (8)	0.0353 (7)	0.0437 (7)	−0.0160 (6)	−0.0124 (6)	0.0001 (5)

Geometric parameters (Å, º) top

O1—C1	1.2996 (16)	C5—C6	1.3832 (19)
O2—C1	1.2300 (15)	C6—C7	1.3774 (19)
O3—N1	1.2204 (17)	C7—C8	1.3759 (19)
O4—N1	1.2185 (16)	C8—C9	1.3855 (19)
O1—H1	0.93 (2)	C3—H3	0.9300
N1—C7	1.4698 (17)	C5—H5	0.9300
C1—C2	1.4880 (18)	C6—H6	0.9300
C2—C3	1.3376 (18)	C8—H8	0.9300
C2—C10	1.4965 (19)	C9—H9	0.9300
C3—C4	1.4770 (18)	C10—H10A	0.9600
C4—C9	1.3887 (18)	C10—H10B	0.9600
C4—C5	1.3951 (18)	C10—H10C	0.9600

O1···C8ⁱ	3.3471 (17)	C4···H10C	2.7200
O1···C6ⁱⁱ	3.4128 (19)	C4···H3ⁱⁱ	3.0300
O1···O2ⁱⁱⁱ	2.6333 (15)	C9···H10C	2.6400
O2···O1ⁱⁱⁱ	2.6333 (15)	C10···H9	2.8300
O2···C1ⁱⁱⁱ	3.3657 (16)	C10···H10B^v	3.0700
O2···N1^iv	3.1112 (17)	H1···O1ⁱⁱⁱ	2.882 (17)
O1···H1ⁱⁱⁱ	2.882 (17)	H1···O2ⁱⁱⁱ	1.71 (2)
O1···H3	2.3100	H1···C1ⁱⁱⁱ	2.59 (2)
O1···H8ⁱ	2.5500	H1···H1ⁱⁱⁱ	2.36 (2)
O2···H10B	2.8600	H3···O1	2.3100
O2···H10A	2.5900	H3···H5	2.5900
O2···H1ⁱⁱⁱ	1.71 (2)	H3···C4ⁱⁱ	3.0300
O2···H9^v	2.6000	H5···O4ⁱ	2.6300
O3···H6	2.4400	H5···H3	2.5900
O3···H10A^vi	2.7600	H6···O3	2.4400
O3···H6^vii	2.6500	H6···O3^vii	2.6500
O3···H10C^viii	2.7800	H6···C2^x	3.0800
O4···H5^ix	2.6300	H8···O1^ix	2.5500
O4···H8	2.4200	H8···O4	2.4200
O4···H10A^vi	2.7400	H9···C2	2.9300
O4···H10C^viii	2.8500	H9···C10	2.8300
N1···O2^vi	3.1112 (17)	H9···H10C	2.4200
N1···C8^viii	3.378 (2)	H9···O2^v	2.6000
C1···O2ⁱⁱⁱ	3.3657 (16)	H10A···O2	2.5900
C2···C6^x	3.5837 (19)	H10A···O3^iv	2.7600
C6···O1ⁱⁱ	3.4128 (19)	H10A···O4^iv	2.7400
C6···C2^x	3.5837 (19)	H10B···O2	2.8600
C8···N1^viii	3.378 (2)	H10B···C1^v	3.0800
C8···O1^ix	3.3471 (17)	H10B···C2^v	2.9500
C9···C10	3.1937 (19)	H10B···C10^v	3.0700
C10···C9	3.1937 (19)	H10B···H10B^v	2.4000
C1···H10B^v	3.0800	H10C···C4	2.7200
C1···H1ⁱⁱⁱ	2.59 (2)	H10C···C9	2.6400
C2···H9	2.9300	H10C···H9	2.4200
C2···H10B^v	2.9500	H10C···O3^viii	2.7800
C2···H6^x	3.0800	H10C···O4^viii	2.8500

C1—O1—H1	111.6 (12)	C7—C8—C9	118.33 (12)
O3—N1—O4	123.45 (13)	C4—C9—C8	120.81 (12)
O3—N1—C7	118.21 (12)	C2—C3—H3	117.00
O4—N1—C7	118.33 (12)	C4—C3—H3	117.00
O1—C1—O2	122.55 (12)	C4—C5—H5	120.00
O1—C1—C2	116.77 (11)	C6—C5—H5	120.00
O2—C1—C2	120.68 (11)	C5—C6—H6	121.00
C1—C2—C10	115.28 (11)	C7—C6—H6	121.00
C3—C2—C10	126.40 (12)	C7—C8—H8	121.00
C1—C2—C3	118.29 (11)	C9—C8—H8	121.00
C2—C3—C4	126.35 (12)	C4—C9—H9	120.00
C3—C4—C9	121.47 (11)	C8—C9—H9	120.00
C5—C4—C9	119.09 (12)	C2—C10—H10A	109.00
C3—C4—C5	119.41 (11)	C2—C10—H10B	109.00
C4—C5—C6	120.66 (12)	C2—C10—H10C	109.00
C5—C6—C7	118.38 (12)	H10A—C10—H10B	109.00
N1—C7—C6	119.04 (11)	H10A—C10—H10C	110.00
N1—C7—C8	118.35 (11)	H10B—C10—H10C	109.00
C6—C7—C8	122.61 (12)

O3—N1—C7—C6	−7.7 (2)	C2—C3—C4—C9	−44.9 (2)
O3—N1—C7—C8	172.34 (13)	C3—C4—C5—C6	−178.09 (13)
O4—N1—C7—C6	173.58 (14)	C9—C4—C5—C6	3.7 (2)
O4—N1—C7—C8	−6.4 (2)	C3—C4—C9—C8	179.06 (13)
O1—C1—C2—C3	3.07 (18)	C5—C4—C9—C8	−2.7 (2)
O1—C1—C2—C10	−174.99 (12)	C4—C5—C6—C7	−1.4 (2)
O2—C1—C2—C3	−176.04 (13)	C5—C6—C7—N1	178.15 (13)
O2—C1—C2—C10	5.90 (18)	C5—C6—C7—C8	−1.9 (2)
C1—C2—C3—C4	176.84 (12)	N1—C7—C8—C9	−177.24 (13)
C10—C2—C3—C4	−5.3 (2)	C6—C7—C8—C9	2.8 (2)
C2—C3—C4—C5	136.88 (15)	C7—C8—C9—C4	−0.4 (2)

Symmetry codes: (i) x, y−1, z; (ii) −x, −y+1, −z; (iii) −x, −y, −z+1; (iv) x, y−1, z+1; (v) −x, −y+1, −z+1; (vi) x, y+1, z−1; (vii) −x+1, −y+2, −z−1; (viii) −x+1, −y+2, −z; (ix) x, y+1, z; (x) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱⁱⁱ	0.93 (2)	1.71 (2)	2.6333 (15)	177 (2)
C3—H3···O1	0.93	2.31	2.7080 (17)	105
C8—H8···O1^ix	0.93	2.55	3.3471 (17)	144
C9—H9···O2^v	0.93	2.60	3.4912 (17)	161

Symmetry codes: (iii) −x, −y, −z+1; (v) −x, −y+1, −z+1; (ix) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₉NO₄
M_r	207.18
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.3878 (3), 8.1050 (5), 8.3402 (4)
α, β, γ (°)	75.793 (2), 81.835 (3), 87.686 (2)
V (Å³)	479.21 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.970, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	9039, 2518, 1926
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.134, 1.02
No. of reflections	2518
No. of parameters	140
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.21

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Selected bond lengths (Å) top

O1—C1	1.2996 (16)	O4—N1	1.2185 (16)
O2—C1	1.2300 (15)	N1—C7	1.4698 (17)
O3—N1	1.2204 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.93 (2)	1.71 (2)	2.6333 (15)	177 (2)
C3—H3···O1	0.93	2.31	2.7080 (17)	105
C8—H8···O1ⁱⁱ	0.93	2.55	3.3471 (17)	144
C9—H9···O2ⁱⁱⁱ	0.93	2.60	3.4912 (17)	161

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

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore and for financial support to Niaz Muhammad for PhD studies under the Indigenous Scholarship Scheme.

References

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