2-[(4-Methoxy-phen-yl)imino-meth-yl]-4-nitro-phenol.

The title Schiff base compound, C(14)H(12)N(2)O(4), is in an inter-mediate state between NH and OH tautomers. Apart from the intra-molecular O-H⋯N hydrogen bond, there are inter-molecular C-H⋯O hydrogen bonds, generating centrosymmetric R(2) (2)(18) and R(2) (2)(14) dimers.

Related literature

For a related structure, see: Karabıyık et al. (2007 ▶). For geometric parameters, see: Allen et al. (1987 ▶); Glidewell et al. (2004 ▶); Zeller & Hunter (2004 ▶).

Experimental

Crystal data

C14H12N2O4

M = 272.26

Monoclinic,

a = 3.8883 (3) Å

b = 21.6202 (17) Å

c = 15.3127 (11) Å

β = 97.887 (1)°

V = 1275.10 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.80 × 0.22 × 0.21 mm

Data collection

Stoe IPDS-II diffractometer

Absorption correction: integration (X-RED; Stoe & Cie, 2002 ▶) T min = 0.945, T max = 0.982

8242 measured reflections

2501 independent reflections

1710 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.098

S = 1.02

2501 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.09 e Å−3

Δρmin = −0.14 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809008150/bt2883sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008150/bt2883Isup2.hkl

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

C14H12N2O4	F(000) = 568
Mr = 272.26	Dx = 1.418 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12745 reflections
a = 3.8883 (3) Å	θ = 1.6–28.9°
b = 21.6202 (17) Å	µ = 0.11 mm−1
c = 15.3127 (11) Å	T = 296 K
β = 97.887 (1)°	Prism, orange
V = 1275.10 (17) Å3	0.80 × 0.22 × 0.21 mm
Z = 4

Stoe IPDS-II diffractometer	2501 independent reflections
Radiation source: fine-focus sealed tube	1710 reflections with I > 2σ(I)
plane graphite	Rint = 0.033
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 1.6°
rotation method scans	h = −4→4
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −26→22
Tmin = 0.945, Tmax = 0.982	l = −18→18
8242 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0543P)2] where P = (Fo2 + 2Fc2)/3
2501 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 0.09 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Experimental. 168 frames, detector distance = 100 mm

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
H1	0.080 (7)	0.5420 (15)	0.3247 (17)	0.159 (9)*
C1	0.1593 (4)	0.54973 (7)	0.17787 (9)	0.0525 (4)
C2	0.1968 (4)	0.55582 (7)	0.08919 (9)	0.0551 (4)
H2	0.2959	0.5240	0.0603	0.066*
C3	0.0878 (4)	0.60869 (7)	0.04447 (9)	0.0537 (4)
C4	−0.0560 (4)	0.65778 (8)	0.08562 (10)	0.0615 (4)
H4	−0.1280	0.6933	0.0541	0.074*
C5	−0.0899 (4)	0.65300 (8)	0.17316 (10)	0.0639 (4)
H5	−0.1815	0.6860	0.2014	0.077*
C6	0.0109 (4)	0.59926 (7)	0.22101 (9)	0.0566 (4)
C7	0.2677 (4)	0.49350 (7)	0.22438 (9)	0.0569 (4)
H7	0.3680	0.4620	0.1951	0.068*
C8	0.3240 (4)	0.43228 (7)	0.35558 (9)	0.0532 (4)
C9	0.2812 (4)	0.43386 (7)	0.44334 (9)	0.0591 (4)
H9	0.1954	0.4697	0.4661	0.071*
C10	0.3611 (4)	0.38411 (8)	0.49849 (9)	0.0594 (4)
H10	0.3300	0.3863	0.5576	0.071*
C11	0.4880 (4)	0.33088 (7)	0.46477 (9)	0.0554 (4)
C12	0.5339 (4)	0.32849 (8)	0.37667 (10)	0.0654 (4)
H12	0.6206	0.2927	0.3541	0.078*
C13	0.4526 (4)	0.37842 (8)	0.32228 (9)	0.0627 (4)
H13	0.4836	0.3762	0.2632	0.075*
C14	0.5188 (5)	0.27857 (8)	0.60288 (10)	0.0719 (5)
H14A	0.5916	0.2397	0.6295	0.108*
H14B	0.2760	0.2846	0.6059	0.108*
H14C	0.6495	0.3114	0.6339	0.108*
N1	0.2277 (3)	0.48627 (6)	0.30559 (7)	0.0567 (3)
N2	0.1205 (4)	0.61313 (7)	−0.04865 (8)	0.0617 (3)
O1	−0.0338 (3)	0.59470 (6)	0.30459 (7)	0.0713 (3)
O2	0.5770 (3)	0.27862 (5)	0.51285 (7)	0.0696 (3)
O3	0.2895 (3)	0.57320 (6)	−0.08103 (7)	0.0806 (4)
O4	−0.0247 (4)	0.65529 (6)	−0.09199 (7)	0.0860 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0452 (8)	0.0534 (9)	0.0586 (8)	−0.0031 (7)	0.0055 (6)	−0.0084 (6)
C2	0.0523 (9)	0.0528 (9)	0.0607 (8)	−0.0028 (7)	0.0094 (7)	−0.0089 (7)
C3	0.0515 (9)	0.0527 (9)	0.0560 (8)	−0.0061 (7)	0.0040 (6)	−0.0060 (6)
C4	0.0566 (9)	0.0532 (9)	0.0721 (10)	0.0006 (8)	−0.0001 (7)	−0.0049 (7)
C5	0.0640 (10)	0.0580 (10)	0.0692 (9)	0.0066 (8)	0.0079 (7)	−0.0129 (7)
C6	0.0483 (9)	0.0590 (10)	0.0619 (9)	−0.0026 (7)	0.0051 (6)	−0.0121 (7)
C7	0.0521 (9)	0.0580 (10)	0.0610 (9)	−0.0009 (7)	0.0090 (6)	−0.0106 (7)
C8	0.0478 (8)	0.0545 (9)	0.0572 (8)	−0.0005 (7)	0.0069 (6)	−0.0073 (6)
C9	0.0586 (9)	0.0595 (10)	0.0604 (9)	0.0067 (8)	0.0127 (7)	−0.0117 (7)
C10	0.0589 (9)	0.0651 (10)	0.0553 (8)	0.0024 (8)	0.0114 (7)	−0.0094 (7)
C11	0.0476 (8)	0.0576 (10)	0.0605 (8)	−0.0018 (7)	0.0055 (6)	−0.0051 (7)
C12	0.0732 (11)	0.0570 (10)	0.0671 (9)	0.0064 (8)	0.0132 (7)	−0.0126 (7)
C13	0.0708 (11)	0.0648 (10)	0.0538 (8)	0.0036 (8)	0.0129 (7)	−0.0099 (7)
C14	0.0777 (12)	0.0709 (11)	0.0676 (10)	0.0007 (10)	0.0113 (8)	0.0033 (8)
N1	0.0550 (8)	0.0589 (8)	0.0562 (7)	−0.0001 (6)	0.0078 (5)	−0.0069 (5)
N2	0.0646 (8)	0.0566 (8)	0.0632 (8)	−0.0096 (7)	0.0058 (6)	−0.0036 (6)
O1	0.0835 (9)	0.0729 (8)	0.0594 (6)	0.0080 (6)	0.0166 (5)	−0.0120 (5)
O2	0.0800 (8)	0.0604 (7)	0.0687 (7)	0.0070 (6)	0.0115 (5)	−0.0007 (5)
O3	0.0992 (10)	0.0787 (9)	0.0677 (7)	0.0089 (7)	0.0251 (6)	−0.0054 (6)
O4	0.1139 (11)	0.0697 (8)	0.0719 (7)	0.0082 (8)	0.0038 (6)	0.0113 (6)

C1—C2	1.3917 (19)	C9—C10	1.376 (2)
C1—C6	1.421 (2)	C9—H9	0.9300
C1—C7	1.442 (2)	C10—C11	1.380 (2)
C2—C3	1.370 (2)	C10—H10	0.9300
C2—H2	0.9300	C11—O2	1.3669 (18)
C3—C4	1.390 (2)	C11—C12	1.386 (2)
C3—N2	1.4521 (18)	C12—C13	1.374 (2)
C4—C5	1.369 (2)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.401 (2)	C14—O2	1.4275 (17)
C5—H5	0.9300	C14—H14A	0.9600
C6—O1	1.3186 (16)	C14—H14B	0.9600
C7—N1	1.2837 (17)	C14—H14C	0.9600
C7—H7	0.9300	N1—H1	1.38 (3)
C8—C9	1.3770 (19)	N2—O4	1.2196 (17)
C8—C13	1.391 (2)	N2—O3	1.2297 (16)
C8—N1	1.4177 (19)	O1—H1	1.25 (3)
C2—C1—C6	119.07 (14)	C9—C10—C11	118.97 (14)
C2—C1—C7	119.93 (13)	C9—C10—H10	120.5
C6—C1—C7	121.01 (13)	C11—C10—H10	120.5
C3—C2—C1	120.01 (14)	O2—C11—C10	124.40 (13)
C3—C2—H2	120.0	O2—C11—C12	115.88 (14)
C1—C2—H2	120.0	C10—C11—C12	119.71 (15)
C2—C3—C4	121.78 (14)	C13—C12—C11	120.75 (15)
C2—C3—N2	118.91 (13)	C13—C12—H12	119.6
C4—C3—N2	119.31 (14)	C11—C12—H12	119.6
C5—C4—C3	119.01 (15)	C12—C13—C8	119.99 (14)
C5—C4—H4	120.5	C12—C13—H13	120.0
C3—C4—H4	120.5	C8—C13—H13	120.0
C4—C5—C6	121.16 (15)	O2—C14—H14A	109.5
C4—C5—H5	119.4	O2—C14—H14B	109.5
C6—C5—H5	119.4	H14A—C14—H14B	109.5
O1—C6—C5	120.34 (14)	O2—C14—H14C	109.5
O1—C6—C1	120.71 (14)	H14A—C14—H14C	109.5
C5—C6—C1	118.95 (13)	H14B—C14—H14C	109.5
N1—C7—C1	121.00 (14)	C7—N1—C8	124.42 (13)
N1—C7—H7	119.5	C7—N1—H1	102.0 (11)
C1—C7—H7	119.5	C8—N1—H1	133.6 (11)
C9—C8—C13	118.42 (15)	O4—N2—O3	122.58 (14)
C9—C8—N1	116.64 (13)	O4—N2—C3	119.16 (14)
C13—C8—N1	124.94 (13)	O3—N2—C3	118.24 (14)
C10—C9—C8	122.15 (15)	C6—O1—H1	102.6 (12)
C10—C9—H9	118.9	C11—O2—C14	117.30 (13)
C8—C9—H9	118.9
C6—C1—C2—C3	−0.7 (2)	C8—C9—C10—C11	−0.1 (2)
C7—C1—C2—C3	178.72 (14)	C9—C10—C11—O2	179.88 (14)
C1—C2—C3—C4	1.2 (2)	C9—C10—C11—C12	0.3 (2)
C1—C2—C3—N2	−178.21 (12)	O2—C11—C12—C13	179.99 (15)
C2—C3—C4—C5	−0.1 (2)	C10—C11—C12—C13	−0.4 (2)
N2—C3—C4—C5	179.23 (13)	C11—C12—C13—C8	0.3 (2)
C3—C4—C5—C6	−1.3 (2)	C9—C8—C13—C12	−0.1 (2)
C4—C5—C6—O1	−177.85 (14)	N1—C8—C13—C12	−179.22 (15)
C4—C5—C6—C1	1.7 (2)	C1—C7—N1—C8	179.33 (13)
C2—C1—C6—O1	178.89 (13)	C9—C8—N1—C7	176.31 (14)
C7—C1—C6—O1	−0.6 (2)	C13—C8—N1—C7	−4.5 (2)
C2—C1—C6—C5	−0.7 (2)	C2—C3—N2—O4	168.40 (14)
C7—C1—C6—C5	179.89 (14)	C4—C3—N2—O4	−11.0 (2)
C2—C1—C7—N1	−178.28 (13)	C2—C3—N2—O3	−10.2 (2)
C6—C1—C7—N1	1.2 (2)	C4—C3—N2—O3	170.37 (14)
C13—C8—C9—C10	0.0 (2)	C10—C11—O2—C14	3.0 (2)
N1—C8—C9—C10	179.19 (14)	C12—C11—O2—C14	−177.33 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	1.25 (3)	1.38 (3)	2.5547 (18)	153 (2)
C7—H7···O3i	0.93	2.46	3.3014 (19)	151
C10—H10···O1ii	0.93	2.57	3.4605 (18)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	1.25 (3)	1.38 (3)	2.5547 (18)	153 (2)
C7—H7⋯O3i	0.93	2.46	3.3014 (19)	151
C10—H10⋯O1ii	0.93	2.57	3.4605 (18)	160

Symmetry codes: (i) ; (ii) .