N-(4-Hy­droxy­phen­yl)-4-nitro­benzamide

Waris, G.; Siddiqi, H.M.; Flörke, U.; Saeed, S.; Butt, M.S.

doi:10.1107/S1600536813006132

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o526

doi:10.1107/S1600536813006132

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N-(4-Hydroxyphenyl)-4-nitrobenzamide

Ghulam Waris,^a Humaira Masood Siddiqi,^a ^* Ulrich Flörke,^b Shaukat Saeed ^c and M. Saeed Butt ^a

^aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan, ^bUniversität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany, and ^cDepartment of Materials and Metallurgical Engineering (DMME), Pakistan Institute of Engineering and Applied Sciences (PIEAS), Islamabad 45650, Pakistan
^*Correspondence e-mail: humaira_siddiqi@yahoo.com

(Received 2 March 2013; accepted 4 March 2013; online 9 March 2013)

The molecular structure of the title compound, C₁₃H₁₀N₂O₄, shows an almost planar conformation as the benzene rings make a dihedral angle of 2.31 (7)°. The nitro group lies in plane with the benzamide ring, with a C—C—N—O torsion angle of 0.6 (2)°. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link molecules into sheets stacked along [10-1].

Related literature

For background to aromatic polyimides, see: Sheng et al. (2009 ). For the solubilizing role of ether and amide groups in polyimides, see: Litvinov et al. (2010 ). For a related structure, see: Raza et al. (2010 ).

Experimental

Crystal data

C₁₃H₁₀N₂O₄
M_r = 258.23
Monoclinic, P 2₁ /c
a = 7.5187 (5) Å
b = 12.5695 (9) Å
c = 11.7932 (8) Å
β = 90.033 (2)°
V = 1114.53 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 130 K
0.50 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.944, T_max = 0.986
10323 measured reflections
2657 independent reflections
2255 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.122
S = 1.12
2657 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O1ⁱ	0.84	1.94	2.7803 (17)	175
N1—H1A⋯O3ⁱⁱ	0.88	2.33	3.1664 (18)	159
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813006132/tk5203sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813006132/tk5203Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813006132/tk5203Isup3.cml

checkCIF report

Comment top

Fairly high thermooxidative and outstanding thermal stability, exceptional mechanical and electrical properties and upright chemical resistance are some distinctions of aromatic polyimides that make them documented as high performance polymeric materials (Sheng et al., 2009). The reported title compound, (I), containing ether and amide groups, serve multiple purposes, such as a boost in solubility and upsurge thermal stability of the resulting polyimide (Litvinov et al., 2010). In this connection, the title compound was investigated.

The molecular structure of (I), Fig. 1, is approximately planar with the dihedral angle between the two benzene rings being 2.31 (7)°. Intermolecular N—H···O and O—H···O hydrogen bonds, Table 1, link molecules into sheets stacked approximately along [1 0 1], Fig. 2. The structure of the isomeric 2-hydroxy-N-(3-nitrophenyl)benzamide compound is known (Raza et al., 2010).

Related literature top

For background to aromatic polyimides, see: Sheng et al. (2009). For the solubilizing role of ether and amide groups in polyimides, see: Litvinov et al. (2010). For a related structure, see: Raza et al. (2010).

Experimental top

Reagent grade quality chemicals were used in this preparation. 4-Aminophenol (0.94 g, 8.6 mmol) in dry dichloromethane (30 ml), a few drops of N, N-dimethylformamide (DMF) and triethylamine (1.25 ml, 8.6 mmol) were placed in a 100 ml, three necked, round bottomed flask, equipped with a condenser, a nitrogen gas inlet tube, a thermometer and a magnetic stirrer. The mixture was stirred at 273–278 K for 30–45 minutes. A solution of 4-nitrobenzoyl chloride (1.59 g, 8.6 mmol) in dichloromethane (20 ml) was added drop-wise via a dropping funnel along with continuous stirring. The reaction mixture was then refluxed for 45 minutes. The flask contents were cooled to room temperature, poured into water and let to stand for 24 h. The resulting bright-yellow precipitate was filtered, washed with hot water and 5% NaOH solution. Finally, product was washed with hot water and dried under vacuum at 350 K. The crude product was recrystallized from ethanol and dichloromethane (2:1, v/v). Yield: 91%; m.p. 406–407 K.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

	Fig. 1. Molecular structure of the title compound with anisotropic displacement parameters drawn at the 50% probability level.
	Fig. 2. Crystal packing viewed along c axis with hydrogen bonds as dotted lines. H-atoms not involved are omitted.

N-(4-Hydroxyphenyl)-4-nitrobenzamide top

Crystal data top

C₁₃H₁₀N₂O₄	F(000) = 536
M_r = 258.23	D_x = 1.539 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2515 reflections
a = 7.5187 (5) Å	θ = 3.2–28.1°
b = 12.5695 (9) Å	µ = 0.12 mm⁻¹
c = 11.7932 (8) Å	T = 130 K
β = 90.033 (2)°	Prism, yellow
V = 1114.53 (13) Å³	0.50 × 0.16 × 0.12 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	2657 independent reflections
Radiation source: sealed tube	2255 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 27.9°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
T_min = 0.944, T_max = 0.986	k = −16→16
10323 measured reflections	l = −15→14

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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F²) = 0.122	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0417P)² + 0.8505P] where P = (F_o² + 2F_c²)/3
2657 reflections	(Δ/σ)_max < 0.001
174 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₃H₁₀N₂O₄	V = 1114.53 (13) Å³
M_r = 258.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5187 (5) Å	µ = 0.12 mm⁻¹
b = 12.5695 (9) Å	T = 130 K
c = 11.7932 (8) Å	0.50 × 0.16 × 0.12 mm
β = 90.033 (2)°

Data collection top

Bruker SMART APEX diffractometer	2657 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2255 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.986	R_int = 0.030
10323 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.12	Δρ_max = 0.37 e Å⁻³
2657 reflections	Δρ_min = −0.28 e Å⁻³
174 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

	x	y	z	U_iso*/U_eq
O1	0.39417 (17)	0.43715 (9)	0.63125 (11)	0.0247 (3)
O2	0.0650 (2)	0.00255 (10)	0.33969 (12)	0.0320 (3)
O3	−0.01095 (17)	0.10678 (10)	0.20187 (10)	0.0239 (3)
O4	0.41630 (19)	0.95533 (9)	0.66718 (11)	0.0284 (3)
H4	0.4704	0.9534	0.7295	0.043*
N1	0.23878 (18)	0.54813 (10)	0.51520 (12)	0.0176 (3)
H1A	0.1612	0.5484	0.4593	0.021*
N2	0.05435 (19)	0.09059 (11)	0.29598 (12)	0.0195 (3)
C1	0.2983 (2)	0.45176 (13)	0.54794 (13)	0.0166 (3)
C2	0.2378 (2)	0.35909 (12)	0.47682 (14)	0.0166 (3)
C3	0.1658 (2)	0.37062 (13)	0.36841 (14)	0.0190 (3)
H3A	0.1579	0.4393	0.3351	0.023*
C4	0.1057 (2)	0.28251 (13)	0.30913 (14)	0.0182 (3)
H4A	0.0541	0.2901	0.2360	0.022*
C5	0.1225 (2)	0.18327 (12)	0.35856 (14)	0.0176 (3)
C6	0.1982 (2)	0.16825 (13)	0.46470 (15)	0.0197 (3)
H6A	0.2098	0.0991	0.4962	0.024*
C7	0.2562 (2)	0.25726 (13)	0.52325 (14)	0.0186 (3)
H7A	0.3091	0.2491	0.5959	0.022*
C8	0.2858 (2)	0.64971 (12)	0.55977 (14)	0.0166 (3)
C9	0.2564 (2)	0.73771 (13)	0.49077 (14)	0.0188 (3)
H9A	0.2055	0.7280	0.4177	0.023*
C10	0.3001 (2)	0.83960 (13)	0.52705 (15)	0.0209 (4)
H10A	0.2796	0.8991	0.4791	0.025*
C11	0.3742 (2)	0.85379 (13)	0.63415 (14)	0.0193 (3)
C12	0.4006 (2)	0.76651 (13)	0.70399 (14)	0.0190 (3)
H12A	0.4498	0.7764	0.7774	0.023*
C13	0.3560 (2)	0.66451 (13)	0.66782 (14)	0.0189 (3)
H13A	0.3734	0.6053	0.7167	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0316 (7)	0.0198 (6)	0.0226 (6)	0.0025 (5)	−0.0140 (5)	−0.0023 (5)
O2	0.0488 (9)	0.0149 (6)	0.0323 (8)	−0.0020 (5)	−0.0158 (6)	0.0000 (5)
O3	0.0293 (7)	0.0230 (6)	0.0194 (6)	−0.0011 (5)	−0.0082 (5)	−0.0039 (5)
O4	0.0435 (8)	0.0158 (6)	0.0258 (7)	−0.0030 (5)	−0.0152 (6)	−0.0019 (5)
N1	0.0214 (7)	0.0149 (6)	0.0163 (7)	−0.0002 (5)	−0.0078 (5)	−0.0012 (5)
N2	0.0219 (7)	0.0166 (7)	0.0201 (7)	0.0015 (5)	−0.0043 (6)	−0.0023 (5)
C1	0.0172 (8)	0.0168 (8)	0.0157 (7)	−0.0005 (6)	−0.0017 (6)	−0.0007 (6)
C2	0.0159 (8)	0.0166 (8)	0.0173 (8)	0.0006 (6)	−0.0023 (6)	−0.0019 (6)
C3	0.0222 (8)	0.0154 (7)	0.0194 (8)	0.0014 (6)	−0.0039 (6)	0.0012 (6)
C4	0.0197 (8)	0.0189 (8)	0.0160 (8)	0.0011 (6)	−0.0037 (6)	−0.0017 (6)
C5	0.0181 (8)	0.0155 (7)	0.0193 (8)	0.0005 (6)	−0.0025 (6)	−0.0035 (6)
C6	0.0229 (8)	0.0157 (8)	0.0204 (8)	0.0007 (6)	−0.0038 (6)	0.0018 (6)
C7	0.0215 (8)	0.0189 (8)	0.0153 (8)	0.0011 (6)	−0.0049 (6)	0.0012 (6)
C8	0.0166 (8)	0.0153 (7)	0.0180 (8)	−0.0002 (6)	−0.0018 (6)	−0.0038 (6)
C9	0.0215 (8)	0.0194 (8)	0.0154 (8)	0.0000 (6)	−0.0053 (6)	−0.0014 (6)
C10	0.0265 (9)	0.0158 (8)	0.0203 (8)	0.0001 (6)	−0.0061 (7)	0.0017 (6)
C11	0.0209 (8)	0.0164 (8)	0.0206 (8)	−0.0003 (6)	−0.0040 (6)	−0.0031 (6)
C12	0.0208 (8)	0.0204 (8)	0.0159 (8)	−0.0001 (6)	−0.0051 (6)	−0.0031 (6)
C13	0.0227 (8)	0.0175 (8)	0.0167 (8)	0.0004 (6)	−0.0042 (6)	0.0015 (6)

Geometric parameters (Å, º) top

O1—C1	1.232 (2)	C4—H4A	0.9500
O2—N2	1.2234 (19)	C5—C6	1.388 (2)
O3—N2	1.2303 (18)	C6—C7	1.385 (2)
O4—C11	1.3715 (19)	C6—H6A	0.9500
O4—H4	0.8400	C7—H7A	0.9500
N1—C1	1.348 (2)	C8—C9	1.391 (2)
N1—C8	1.4252 (19)	C8—C13	1.391 (2)
N1—H1A	0.8800	C9—C10	1.390 (2)
N2—C5	1.471 (2)	C9—H9A	0.9500
C1—C2	1.505 (2)	C10—C11	1.392 (2)
C2—C3	1.396 (2)	C10—H10A	0.9500
C2—C7	1.399 (2)	C11—C12	1.386 (2)
C3—C4	1.385 (2)	C12—C13	1.392 (2)
C3—H3A	0.9500	C12—H12A	0.9500
C4—C5	1.383 (2)	C13—H13A	0.9500

C11—O4—H4	109.5	C7—C6—H6A	121.0
C1—N1—C8	128.11 (13)	C5—C6—H6A	121.0
C1—N1—H1A	115.9	C6—C7—C2	120.87 (15)
C8—N1—H1A	115.9	C6—C7—H7A	119.6
O2—N2—O3	123.76 (14)	C2—C7—H7A	119.6
O2—N2—C5	118.84 (14)	C9—C8—C13	119.32 (15)
O3—N2—C5	117.40 (14)	C9—C8—N1	117.21 (14)
O1—C1—N1	123.81 (15)	C13—C8—N1	123.47 (14)
O1—C1—C2	120.35 (14)	C10—C9—C8	121.01 (15)
N1—C1—C2	115.83 (14)	C10—C9—H9A	119.5
C3—C2—C7	119.45 (14)	C8—C9—H9A	119.5
C3—C2—C1	123.16 (14)	C9—C10—C11	119.47 (15)
C7—C2—C1	117.40 (14)	C9—C10—H10A	120.3
C4—C3—C2	120.36 (15)	C11—C10—H10A	120.3
C4—C3—H3A	119.8	O4—C11—C12	122.33 (15)
C2—C3—H3A	119.8	O4—C11—C10	117.98 (14)
C5—C4—C3	118.63 (15)	C12—C11—C10	119.68 (15)
C5—C4—H4A	120.7	C11—C12—C13	120.82 (15)
C3—C4—H4A	120.7	C11—C12—H12A	119.6
C4—C5—C6	122.69 (15)	C13—C12—H12A	119.6
C4—C5—N2	118.13 (14)	C8—C13—C12	119.67 (15)
C6—C5—N2	119.17 (14)	C8—C13—H13A	120.2
C7—C6—C5	117.95 (15)	C12—C13—H13A	120.2

C8—N1—C1—O1	6.9 (3)	N2—C5—C6—C7	−178.04 (15)
C8—N1—C1—C2	−174.10 (15)	C5—C6—C7—C2	0.4 (3)
O1—C1—C2—C3	−164.50 (16)	C3—C2—C7—C6	−2.3 (3)
N1—C1—C2—C3	16.5 (2)	C1—C2—C7—C6	177.81 (15)
O1—C1—C2—C7	15.4 (2)	C1—N1—C8—C9	158.93 (17)
N1—C1—C2—C7	−163.60 (15)	C1—N1—C8—C13	−22.1 (3)
C7—C2—C3—C4	2.8 (2)	C13—C8—C9—C10	1.7 (3)
C1—C2—C3—C4	−177.28 (15)	N1—C8—C9—C10	−179.33 (16)
C2—C3—C4—C5	−1.4 (2)	C8—C9—C10—C11	−0.1 (3)
C3—C4—C5—C6	−0.5 (3)	C9—C10—C11—O4	179.79 (16)
C3—C4—C5—N2	178.57 (15)	C9—C10—C11—C12	−1.1 (3)
O2—N2—C5—C4	−178.54 (16)	O4—C11—C12—C13	179.87 (16)
O3—N2—C5—C4	1.3 (2)	C10—C11—C12—C13	0.8 (3)
O2—N2—C5—C6	0.6 (2)	C9—C8—C13—C12	−1.9 (3)
O3—N2—C5—C6	−179.59 (15)	N1—C8—C13—C12	179.11 (15)
C4—C5—C6—C7	1.0 (3)	C11—C12—C13—C8	0.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1ⁱ	0.84	1.94	2.7803 (17)	175
N1—H1A···O3ⁱⁱ	0.88	2.33	3.1664 (18)	159

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀N₂O₄
M_r	258.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	130
a, b, c (Å)	7.5187 (5), 12.5695 (9), 11.7932 (8)
β (°)	90.033 (2)
V (Å³)	1114.53 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.50 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.944, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	10323, 2657, 2255
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.122, 1.12
No. of reflections	2657
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.28

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1ⁱ	0.84	1.94	2.7803 (17)	175
N1—H1A···O3ⁱⁱ	0.88	2.33	3.1664 (18)	159

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

Acknowledgements

The contribution to this project of the Higher Education Commission of Pakistan by providing financial assistance through the International Research Support Initiative Programme (IRSIP) is acknowledged by the authors.

References

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