2-[N-(3-Amino-4-nitro-phen-yl)carboximido-yl]phenol.

The title compound, C(13)H(11)N(3)O(3), is essentially planar (r.m.s. for the 19 non-H atoms = 0.031 Å), a conformation stabilized in part by intra-molecular O-H⋯N and N-H⋯O hydrogen bonds. The configuration about the imine bond [1.2919 (12) Å] is E. The presence of N-H⋯O(nitro) hydrogen bonds leads to the formation of supra-molecular tapes in the crystal structure. These are connected into layers by π-π inter-actions [centroid-centroid distance = 3.6046 (6) Å] occurring between the hy-droxy- and amino-substituted benzene rings.

Related literature

For related work on Schiff bases, see: Prasath et al. (2010 ▶); Shahverdizadeh & Tiekink (2011 ▶). For specialized crystallization techniques, see: Harrowfield et al. (1996 ▶).

Experimental

Crystal data

C13H11N3O3

M = 257.25

Triclinic,

a = 7.0961 (3) Å

b = 7.5168 (4) Å

c = 12.1627 (6) Å

α = 100.067 (4)°

β = 94.751 (4)°

γ = 115.011 (5)°

V = 569.87 (5) Å3

Z = 2

Cu Kα radiation

μ = 0.92 mm−1

T = 100 K

0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.748, T max = 1.000

3654 measured reflections

2231 independent reflections

2105 reflections with I > 2σ(I)

R int = 0.008

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.113

S = 1.07

2231 reflections

184 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681104181X/hg5110sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104181X/hg5110Isup2.hkl

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

C13H11N3O3	Z = 2
Mr = 257.25	F(000) = 268
Triclinic, P1	Dx = 1.499 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 7.0961 (3) Å	Cell parameters from 2525 reflections
b = 7.5168 (4) Å	θ = 3.8–74.1°
c = 12.1627 (6) Å	µ = 0.92 mm−1
α = 100.067 (4)°	T = 100 K
β = 94.751 (4)°	Prism, orange
γ = 115.011 (5)°	0.25 × 0.20 × 0.15 mm
V = 569.87 (5) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	2231 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2105 reflections with I > 2σ(I)
Mirror	Rint = 0.008
Detector resolution: 10.4041 pixels mm-1	θmax = 74.3°, θmin = 3.8°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −9→9
Tmin = 0.748, Tmax = 1.000	l = −13→15
3654 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0753P)2 + 0.0839P] where P = (Fo2 + 2Fc2)/3
2231 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.28 e Å−3
3 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	0.40452 (11)	0.27962 (11)	0.59127 (6)	0.0227 (2)
H1o	0.495 (2)	0.285 (3)	0.5475 (13)	0.062 (5)*
O2	1.09653 (11)	0.36753 (12)	0.05261 (6)	0.0246 (2)
O3	1.31365 (10)	0.29051 (11)	0.14605 (6)	0.0233 (2)
N1	0.71614 (12)	0.25239 (11)	0.50498 (7)	0.0158 (2)
N2	0.78293 (13)	0.40302 (13)	0.14327 (7)	0.0191 (2)
H1n	0.840 (2)	0.420 (2)	0.0816 (9)	0.039 (4)*
H2n	0.6610 (15)	0.4021 (18)	0.1447 (10)	0.026 (3)*
N3	1.15808 (12)	0.32599 (12)	0.13890 (7)	0.0172 (2)
C1	0.47038 (15)	0.22517 (14)	0.68163 (8)	0.0168 (2)
C2	0.36032 (15)	0.21048 (14)	0.77211 (8)	0.0197 (2)
H2	0.2408	0.2372	0.7690	0.024*
C3	0.42483 (16)	0.15713 (14)	0.86643 (8)	0.0209 (2)
H3	0.3500	0.1491	0.9281	0.025*
C4	0.59855 (15)	0.11503 (14)	0.87207 (8)	0.0202 (2)
H4	0.6405	0.0763	0.9366	0.024*
C5	0.70904 (15)	0.13020 (14)	0.78289 (8)	0.0182 (2)
H5	0.8283	0.1031	0.7870	0.022*
C6	0.64775 (14)	0.18514 (13)	0.68626 (8)	0.0155 (2)
C7	0.76768 (14)	0.20111 (13)	0.59454 (8)	0.0161 (2)
H7	0.8864	0.1733	0.6004	0.019*
C8	0.83502 (14)	0.27202 (13)	0.41602 (8)	0.0146 (2)
C9	0.76291 (14)	0.32620 (13)	0.32488 (8)	0.0151 (2)
H9	0.6412	0.3491	0.3265	0.018*
C10	0.86365 (14)	0.34913 (13)	0.22862 (8)	0.0150 (2)
C11	1.04545 (14)	0.31485 (13)	0.23212 (8)	0.0150 (2)
C12	1.12150 (14)	0.26527 (14)	0.32711 (8)	0.0168 (2)
H12	1.2463	0.2472	0.3281	0.020*
C13	1.01929 (15)	0.24257 (14)	0.41788 (8)	0.0172 (2)
H13	1.0711	0.2076	0.4812	0.021*

	U11	U22	U33	U12	U13	U23
O1	0.0209 (4)	0.0344 (4)	0.0206 (4)	0.0173 (3)	0.0055 (3)	0.0120 (3)
O2	0.0274 (4)	0.0366 (4)	0.0191 (4)	0.0190 (3)	0.0095 (3)	0.0143 (3)
O3	0.0206 (4)	0.0328 (4)	0.0259 (4)	0.0180 (3)	0.0105 (3)	0.0104 (3)
N1	0.0162 (4)	0.0170 (4)	0.0136 (4)	0.0067 (3)	0.0031 (3)	0.0038 (3)
N2	0.0185 (4)	0.0274 (4)	0.0183 (4)	0.0143 (3)	0.0067 (3)	0.0102 (3)
N3	0.0166 (4)	0.0173 (4)	0.0184 (4)	0.0077 (3)	0.0051 (3)	0.0047 (3)
C1	0.0167 (5)	0.0163 (4)	0.0164 (5)	0.0068 (4)	0.0018 (4)	0.0036 (3)
C2	0.0183 (5)	0.0190 (4)	0.0219 (5)	0.0088 (4)	0.0054 (4)	0.0028 (4)
C3	0.0241 (5)	0.0193 (5)	0.0166 (5)	0.0066 (4)	0.0082 (4)	0.0032 (4)
C4	0.0240 (5)	0.0201 (4)	0.0146 (5)	0.0079 (4)	0.0023 (4)	0.0052 (3)
C5	0.0182 (5)	0.0179 (5)	0.0181 (5)	0.0076 (4)	0.0023 (4)	0.0048 (3)
C6	0.0157 (4)	0.0141 (4)	0.0149 (5)	0.0054 (3)	0.0019 (3)	0.0027 (3)
C7	0.0153 (5)	0.0160 (4)	0.0170 (5)	0.0071 (4)	0.0031 (4)	0.0036 (4)
C8	0.0135 (4)	0.0140 (4)	0.0146 (5)	0.0049 (3)	0.0030 (3)	0.0021 (3)
C9	0.0140 (4)	0.0157 (4)	0.0163 (5)	0.0073 (3)	0.0030 (4)	0.0033 (4)
C10	0.0153 (4)	0.0132 (4)	0.0153 (5)	0.0055 (3)	0.0025 (3)	0.0031 (3)
C11	0.0148 (4)	0.0153 (4)	0.0151 (5)	0.0063 (4)	0.0046 (4)	0.0039 (3)
C12	0.0138 (4)	0.0179 (4)	0.0195 (5)	0.0079 (4)	0.0025 (3)	0.0038 (3)
C13	0.0171 (4)	0.0207 (5)	0.0152 (5)	0.0094 (4)	0.0019 (3)	0.0056 (3)

O1—C1	1.3519 (11)	C4—C5	1.3830 (13)
O1—H1o	0.858 (9)	C4—H4	0.9500
O2—N3	1.2424 (10)	C5—C6	1.4064 (13)
O3—N3	1.2403 (10)	C5—H5	0.9500
N1—C7	1.2919 (12)	C6—C7	1.4494 (13)
N1—C8	1.4163 (12)	C7—H7	0.9500
N2—C10	1.3471 (12)	C8—C9	1.3772 (13)
N2—H1n	0.885 (9)	C8—C13	1.4145 (13)
N2—H2n	0.864 (8)	C9—C10	1.4200 (12)
N3—C11	1.4346 (12)	C9—H9	0.9500
C1—C2	1.3947 (14)	C10—C11	1.4172 (13)
C1—C6	1.4115 (14)	C11—C12	1.4079 (13)
C2—C3	1.3840 (14)	C12—C13	1.3668 (13)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.3957 (15)	C13—H13	0.9500
C3—H3	0.9500
C1—O1—H1o	104.2 (12)	C5—C6—C7	119.76 (9)
C7—N1—C8	121.52 (8)	C1—C6—C7	121.50 (9)
C10—N2—H1n	122.2 (10)	N1—C7—C6	121.24 (9)
C10—N2—H2n	117.9 (8)	N1—C7—H7	119.4
H1n—N2—H2n	119.2 (12)	C6—C7—H7	119.4
O3—N3—O2	121.55 (8)	C9—C8—C13	120.23 (9)
O3—N3—C11	118.76 (8)	C9—C8—N1	115.89 (8)
O2—N3—C11	119.68 (8)	C13—C8—N1	123.87 (8)
O1—C1—C2	118.68 (9)	C8—C9—C10	122.45 (8)
O1—C1—C6	121.45 (9)	C8—C9—H9	118.8
C2—C1—C6	119.87 (9)	C10—C9—H9	118.8
C3—C2—C1	120.17 (9)	N2—C10—C11	125.47 (8)
C3—C2—H2	119.9	N2—C10—C9	118.58 (8)
C1—C2—H2	119.9	C11—C10—C9	115.95 (8)
C2—C3—C4	120.79 (9)	C12—C11—C10	121.18 (9)
C2—C3—H3	119.6	C12—C11—N3	117.08 (8)
C4—C3—H3	119.6	C10—C11—N3	121.73 (8)
C5—C4—C3	119.36 (9)	C13—C12—C11	121.27 (9)
C5—C4—H4	120.3	C13—C12—H12	119.4
C3—C4—H4	120.3	C11—C12—H12	119.4
C4—C5—C6	121.07 (9)	C12—C13—C8	118.89 (9)
C4—C5—H5	119.5	C12—C13—H13	120.6
C6—C5—H5	119.5	C8—C13—H13	120.6
C5—C6—C1	118.73 (9)
O1—C1—C2—C3	−179.34 (8)	N1—C8—C9—C10	−179.14 (7)
C6—C1—C2—C3	0.12 (15)	C8—C9—C10—N2	−179.84 (8)
C1—C2—C3—C4	−0.76 (15)	C8—C9—C10—C11	−0.63 (14)
C2—C3—C4—C5	1.05 (15)	N2—C10—C11—C12	177.90 (8)
C3—C4—C5—C6	−0.70 (15)	C9—C10—C11—C12	−1.25 (13)
C4—C5—C6—C1	0.07 (14)	N2—C10—C11—N3	−3.06 (15)
C4—C5—C6—C7	179.57 (8)	C9—C10—C11—N3	177.79 (7)
O1—C1—C6—C5	179.66 (7)	O3—N3—C11—C12	0.51 (13)
C2—C1—C6—C5	0.22 (14)	O2—N3—C11—C12	179.41 (7)
O1—C1—C6—C7	0.17 (15)	O3—N3—C11—C10	−178.57 (8)
C2—C1—C6—C7	−179.27 (8)	O2—N3—C11—C10	0.32 (13)
C8—N1—C7—C6	178.78 (7)	C10—C11—C12—C13	1.95 (14)
C5—C6—C7—N1	−179.59 (7)	N3—C11—C12—C13	−177.14 (8)
C1—C6—C7—N1	−0.10 (15)	C11—C12—C13—C8	−0.71 (14)
C7—N1—C8—C9	179.58 (7)	C9—C8—C13—C12	−1.16 (14)
C7—N1—C8—C13	−1.46 (15)	N1—C8—C13—C12	179.92 (8)
C13—C8—C9—C10	1.85 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.86 (1)	1.79 (1)	2.5933 (10)	154.(2)
N2—H1n···O2	0.89 (1)	2.06 (1)	2.6542 (11)	123.(1)
N2—H1n···O2i	0.89 (1)	2.42 (1)	3.1479 (11)	140.(1)
N2—H2n···O3ii	0.86 (1)	2.25 (1)	3.0746 (10)	161.(1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.86 (1)	1.79 (1)	2.5933 (10)	154 (2)
N2—H1n⋯O2	0.89 (1)	2.06 (1)	2.6542 (11)	123 (1)
N2—H1n⋯O2i	0.89 (1)	2.42 (1)	3.1479 (11)	140 (1)
N2—H2n⋯O3ii	0.86 (1)	2.25 (1)	3.0746 (10)	161 (1)

Symmetry codes: (i) ; (ii) .