N-(2-Hydroxy-phen-yl)-4-nitro-phthalimide.

Mol-ecules of the title compound, C(14)H(8)N(2)O(5), are linked by a hydr-oxy-amide O-H⋯O hydrogen bond into a linear chain. The hydr-oxy group is disordered over two positions of the benzene ring in an approximate 0.57:0.43 ratio.

Related literature

For literature on the hydrolysis of N-substituted phthalimides, see: Sim et al. (2006 ▶; 2007 ▶).

Experimental

Crystal data

C14H8N2O5

M = 284.22

Orthorhombic,

a = 7.1114 (2) Å

b = 11.7646 (3) Å

c = 14.5304 (4) Å

V = 1215.65 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 (2) K

0.32 × 0.06 × 0.06 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

13791 measured reflections

1618 independent reflections

1356 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.142

S = 1.04

1618 reflections

199 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025920/lh2681sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025920/lh2681Isup2.hkl

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

C14H8N2O5	F000 = 584
Mr = 284.22	Dx = 1.553 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2147 reflections
a = 7.1114 (2) Å	θ = 2.8–23.8º
b = 11.7646 (3) Å	µ = 0.12 mm−1
c = 14.5304 (4) Å	T = 100 (2) K
V = 1215.65 (6) Å3	Prism, yellow
Z = 4	0.32 × 0.06 × 0.06 mm

Bruker SMART APEX diffractometer	1356 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.087
Monochromator: graphite	θmax = 27.5º
T = 100(2) K	θmin = 2.2º
ω scans	h = −9→9
Absorption correction: None	k = −15→15
13791 measured reflections	l = −18→18
1618 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0803P)2 + 0.3691P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
1618 reflections	Δρmax = 0.36 e Å−3
199 parameters	Δρmin = −0.28 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.3544 (4)	0.2939 (3)	0.8037 (3)	0.0308 (10)	0.571 (3)
H1	0.2490	0.3065	0.7797	0.046*	0.571 (3)
O1'	0.8498 (5)	0.4876 (3)	0.9237 (4)	0.0287 (13)	0.429 (3)
H1'	0.9140	0.4284	0.9162	0.043*	0.429 (3)
O2	0.4761 (4)	0.1944 (2)	0.97117 (17)	0.0362 (6)
O3	0.9695 (3)	0.3018 (2)	0.78879 (18)	0.0347 (6)
O4	1.3585 (4)	−0.0916 (2)	0.8641 (2)	0.0455 (8)
O5	1.1873 (5)	−0.2264 (2)	0.9238 (2)	0.0533 (9)
N1	0.7000 (4)	0.2751 (2)	0.87514 (18)	0.0217 (6)
N2	1.2106 (5)	−0.1285 (3)	0.8959 (2)	0.0383 (8)
C1	0.4328 (5)	0.3850 (3)	0.8206 (2)	0.0307 (8)
H1A	0.3676	0.3163	0.8080	0.037*	0.429 (3)
C2	0.3486 (7)	0.4888 (4)	0.8022 (3)	0.0493 (12)
H2	0.2230	0.4915	0.7800	0.059*
C3	0.4465 (8)	0.5871 (4)	0.8161 (3)	0.0537 (13)
H3	0.3904	0.6578	0.8006	0.064*
C4	0.6260 (9)	0.5852 (3)	0.8525 (3)	0.0543 (14)
H4	0.6931	0.6542	0.8616	0.065*
C5	0.7071 (6)	0.4825 (3)	0.8755 (3)	0.0390 (9)
H5A	0.8276	0.4806	0.9037	0.047*	0.571 (3)
C6	0.6120 (5)	0.3820 (3)	0.8574 (2)	0.0271 (7)
C7	0.6224 (5)	0.1884 (3)	0.9290 (2)	0.0237 (7)
C8	0.7584 (5)	0.0922 (3)	0.9252 (2)	0.0236 (7)
C9	0.7433 (5)	−0.0146 (3)	0.9637 (2)	0.0287 (7)
H9	0.6348	−0.0371	0.9972	0.034*
C10	0.8946 (5)	−0.0877 (3)	0.9510 (2)	0.0305 (8)
H10	0.8915	−0.1625	0.9756	0.037*
C11	1.0478 (5)	−0.0508 (3)	0.9029 (2)	0.0270 (7)
C12	1.0651 (5)	0.0568 (3)	0.8618 (2)	0.0276 (7)
H12	1.1733	0.0793	0.8281	0.033*
C13	0.9122 (4)	0.1269 (3)	0.8746 (2)	0.0244 (7)
C14	0.8758 (4)	0.2439 (3)	0.8398 (2)	0.0226 (7)

	U11	U22	U33	U12	U13	U23
O1	0.021 (2)	0.032 (2)	0.039 (2)	0.0014 (18)	−0.0039 (18)	0.000 (2)
O1'	0.025 (3)	0.023 (2)	0.039 (3)	−0.003 (2)	−0.014 (2)	0.000 (2)
O2	0.0371 (14)	0.0391 (13)	0.0322 (14)	0.0103 (12)	0.0161 (11)	0.0066 (11)
O3	0.0246 (12)	0.0454 (15)	0.0341 (13)	0.0017 (12)	0.0003 (11)	0.0114 (12)
O4	0.0307 (14)	0.0623 (19)	0.0435 (15)	0.0172 (13)	0.0023 (13)	−0.0015 (14)
O5	0.070 (2)	0.0364 (14)	0.0534 (18)	0.0275 (15)	0.0170 (17)	0.0133 (14)
N1	0.0209 (12)	0.0235 (13)	0.0206 (13)	0.0047 (10)	−0.0020 (11)	0.0006 (11)
N2	0.0418 (17)	0.0448 (18)	0.0285 (16)	0.0170 (15)	0.0059 (14)	−0.0016 (15)
C1	0.0310 (17)	0.0420 (19)	0.0191 (15)	0.0149 (16)	0.0059 (13)	0.0048 (15)
C2	0.053 (3)	0.058 (3)	0.036 (2)	0.035 (2)	0.017 (2)	0.025 (2)
C3	0.081 (3)	0.048 (3)	0.032 (2)	0.042 (3)	0.021 (2)	0.0186 (19)
C4	0.109 (4)	0.0286 (19)	0.0250 (19)	0.013 (2)	0.011 (3)	0.0013 (16)
C5	0.066 (3)	0.0290 (17)	0.0217 (18)	0.0023 (18)	−0.0074 (19)	0.0015 (15)
C6	0.0371 (17)	0.0255 (15)	0.0186 (15)	0.0124 (14)	0.0028 (14)	0.0026 (13)
C7	0.0313 (16)	0.0246 (14)	0.0152 (14)	0.0044 (13)	−0.0018 (13)	−0.0005 (12)
C8	0.0268 (15)	0.0257 (15)	0.0184 (15)	0.0057 (12)	0.0005 (13)	−0.0024 (13)
C9	0.0309 (16)	0.0302 (16)	0.0250 (17)	0.0010 (14)	0.0018 (14)	−0.0009 (14)
C10	0.0351 (17)	0.0284 (17)	0.0280 (17)	0.0038 (14)	−0.0024 (15)	−0.0038 (14)
C11	0.0324 (16)	0.0288 (16)	0.0198 (15)	0.0129 (14)	−0.0041 (13)	−0.0051 (14)
C12	0.0255 (15)	0.0382 (18)	0.0191 (15)	0.0056 (14)	−0.0033 (13)	−0.0003 (14)
C13	0.0229 (14)	0.0288 (16)	0.0214 (14)	0.0054 (12)	−0.0057 (13)	−0.0038 (14)
C14	0.0206 (14)	0.0279 (15)	0.0194 (15)	0.0014 (12)	−0.0040 (12)	0.0012 (13)

O1—C1	1.233 (5)	C3—C4	1.382 (8)
O1—H1	0.8400	C3—H3	0.9500
O1'—C5	1.234 (5)	C4—C5	1.380 (6)
O1'—H1'	0.8400	C4—H4	0.9500
O2—C7	1.210 (4)	C5—C6	1.388 (5)
O3—C14	1.207 (4)	C5—H5A	0.9500
O4—N2	1.228 (4)	C7—C8	1.490 (4)
O5—N2	1.232 (4)	C8—C9	1.380 (5)
N1—C14	1.401 (4)	C8—C13	1.379 (4)
N1—C7	1.399 (4)	C9—C10	1.389 (5)
N1—C6	1.428 (4)	C9—H9	0.9500
N2—C11	1.478 (4)	C10—C11	1.366 (5)
C1—C6	1.382 (5)	C10—H10	0.9500
C1—C2	1.386 (5)	C11—C12	1.405 (5)
C1—H1A	0.9500	C12—C13	1.377 (4)
C2—C3	1.365 (8)	C12—H12	0.9500
C2—H2	0.9500	C13—C14	1.490 (5)
C1—O1—H1	109.5	C1—C6—C5	120.1 (3)
C5—O1'—H1'	109.5	C1—C6—N1	119.8 (3)
C14—N1—C7	111.5 (3)	C5—C6—N1	120.1 (3)
C14—N1—C6	123.7 (3)	O2—C7—N1	125.5 (3)
C7—N1—C6	124.8 (3)	O2—C7—C8	128.4 (3)
O4—N2—O5	124.7 (3)	N1—C7—C8	106.1 (3)
O4—N2—C11	118.6 (3)	C9—C8—C13	123.1 (3)
O5—N2—C11	116.7 (3)	C9—C8—C7	128.8 (3)
O1—C1—C6	118.1 (3)	C13—C8—C7	108.1 (3)
O1—C1—C2	122.1 (4)	C8—C9—C10	116.8 (3)
C6—C1—C2	119.7 (4)	C8—C9—H9	121.6
C6—C1—H1A	120.1	C10—C9—H9	121.6
C2—C1—H1A	120.1	C11—C10—C9	119.2 (3)
C3—C2—C1	119.8 (4)	C11—C10—H10	120.4
C3—C2—H2	120.1	C9—C10—H10	120.4
C1—C2—H2	120.1	C10—C11—C12	125.0 (3)
C2—C3—C4	121.0 (4)	C10—C11—N2	117.6 (3)
C2—C3—H3	119.5	C12—C11—N2	117.3 (3)
C4—C3—H3	119.5	C13—C12—C11	114.4 (3)
C5—C4—C3	119.5 (5)	C13—C12—H12	122.8
C5—C4—H4	120.2	C11—C12—H12	122.8
C3—C4—H4	120.2	C12—C13—C8	121.4 (3)
O1'—C5—C4	116.1 (4)	C12—C13—C14	130.2 (3)
O1'—C5—C6	123.4 (3)	C8—C13—C14	108.4 (3)
C4—C5—C6	119.7 (4)	O3—C14—N1	124.8 (3)
C4—C5—H5A	120.1	O3—C14—C13	129.3 (3)
C6—C5—H5A	120.1	N1—C14—C13	105.8 (3)
O1—C1—C2—C3	−175.3 (4)	C13—C8—C9—C10	1.3 (5)
C6—C1—C2—C3	3.3 (5)	C7—C8—C9—C10	−178.6 (3)
C1—C2—C3—C4	−3.1 (6)	C8—C9—C10—C11	0.5 (5)
C2—C3—C4—C5	−0.3 (6)	C9—C10—C11—C12	−1.6 (5)
C3—C4—C5—O1'	−166.2 (4)	C9—C10—C11—N2	176.2 (3)
C3—C4—C5—C6	3.5 (6)	O4—N2—C11—C10	−170.1 (3)
O1—C1—C6—C5	178.5 (4)	O5—N2—C11—C10	9.1 (5)
C2—C1—C6—C5	−0.1 (5)	O4—N2—C11—C12	7.9 (5)
O1—C1—C6—N1	−0.4 (5)	O5—N2—C11—C12	−172.9 (3)
C2—C1—C6—N1	−179.1 (3)	C10—C11—C12—C13	0.9 (5)
O1'—C5—C6—C1	165.7 (4)	N2—C11—C12—C13	−177.0 (3)
C4—C5—C6—C1	−3.2 (5)	C11—C12—C13—C8	1.0 (5)
O1'—C5—C6—N1	−15.3 (6)	C11—C12—C13—C14	−177.8 (3)
C4—C5—C6—N1	175.7 (3)	C9—C8—C13—C12	−2.1 (5)
C14—N1—C6—C1	124.8 (3)	C7—C8—C13—C12	177.8 (3)
C7—N1—C6—C1	−54.7 (4)	C9—C8—C13—C14	176.9 (3)
C14—N1—C6—C5	−54.1 (4)	C7—C8—C13—C14	−3.2 (3)
C7—N1—C6—C5	126.3 (4)	C7—N1—C14—O3	177.4 (3)
C14—N1—C7—O2	176.5 (3)	C6—N1—C14—O3	−2.1 (5)
C6—N1—C7—O2	−3.9 (5)	C7—N1—C14—C13	0.0 (3)
C14—N1—C7—C8	−1.8 (3)	C6—N1—C14—C13	−179.6 (3)
C6—N1—C7—C8	177.8 (3)	C12—C13—C14—O3	3.7 (6)
O2—C7—C8—C9	4.8 (6)	C8—C13—C14—O3	−175.3 (3)
N1—C7—C8—C9	−177.0 (3)	C12—C13—C14—N1	−179.0 (3)
O2—C7—C8—C13	−175.1 (3)	C8—C13—C14—N1	2.1 (3)
N1—C7—C8—C13	3.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.84	1.99	2.747 (4)	149
O1'—H1'···O2ii	0.84	2.23	2.779 (4)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.84	1.99	2.747 (4)	149
O1′—H1′⋯O2ii	0.84	2.23	2.779 (4)	123

Symmetry codes: (i) ; (ii) .