N-(4-Hy-droxy-phen-yl)-4-nitro-benzamide.

The mol-ecular 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 mol-ecules 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 = 258.23

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.122

S = 1.12

2657 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.28 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813006132/tk5203sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006132/tk5203Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H10N2O4	F(000) = 536
Mr = 258.23	Dx = 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

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

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(Fo2) + (0.0417P)2 + 0.8505P] where P = (Fo2 + 2Fc2)/3
2657 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .