Crystal structure of 2-{[2-meth-oxy-5-(tri-fluoro-meth-yl)phen-yl]iminomethyl}-4-nitro-phenol.

In the title compound, C15H11F3N2O4, the N=C bond of the central imine group adopts an E conformation. The dihedral angle between two benzene rings is 6.2 (2)°. There is an intra-molecular bifurcated O-H⋯(N,O) hydrogen bond with S(6) and S(9) ring motifs. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds into a helical chain along the 31 screw axis parallel to c. The -CF3 group shows rotational disorder over two sites, with occupancies of 0.39 (2) and 0.61 (2).

Related literature

For photochromic, thermochromic and biological applications of related Schiff base compounds, see: Hadjoudis et al. (1987 ▸); Santos et al. (2001 ▸); Tarafder et al. (2002 ▸). For related structures, see: Faridbod et al. (2008 ▸); Karadayı et al. (2003 ▸, 2006 ▸, 2013 ▸); Raja et al. (2008 ▸).

Experimental

Crystal data

C15H11F3N2O4

M = 340.26

Trigonal,

a = 33.0327 (16) Å

c = 7.1523 (3) Å

V = 6758.7 (5) Å3

Z = 18

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.67 × 0.25 × 0.04 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▸) T min = 0.951, T max = 0.994

16356 measured reflections

2958 independent reflections

1380 reflections with I > 2σ(I)

R int = 0.140

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.126

S = 1.07

2958 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.19 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, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015010129/is5398sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015010129/is5398Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015010129/is5398Isup3.cml

Click here for additional data file.

ORTEP . DOI: 10.1107/S2056989015010129/is5398fig1.tif

An ORTEP drawing of the title compound showing the atomic numbering scheme. Displacement ellipsoids of non-H atoms are shown at the 20% probability level. Hydrogen bonds are indicated by dashed lines.

CCDC reference: 1402674

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H11F3N2O4	Dx = 1.505 Mg m−3
Mr = 340.26	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 10608 reflections
Hall symbol: -R 3	θ = 2.1–28.0°
a = 33.0327 (16) Å	µ = 0.13 mm−1
c = 7.1523 (3) Å	T = 296 K
V = 6758.7 (5) Å3	Needle, light brown
Z = 18	0.67 × 0.25 × 0.04 mm
F(000) = 3132

Stoe IPDS 2 diffractometer	2958 independent reflections
Radiation source: fine-focus sealed tube	1380 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.140
ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −40→40
Tmin = 0.951, Tmax = 0.994	k = −39→40
16356 measured reflections	l = −8→8

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0292P)2] where P = (Fo2 + 2Fc2)/3
2958 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.19 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	Occ. (<1)
O4	0.76299 (10)	0.04667 (9)	0.2585 (4)	0.0569 (8)
O1	0.76808 (9)	0.14868 (10)	0.4121 (5)	0.0647 (9)
H1	0.7798	0.1330	0.3798	0.097*
N1	0.83251 (11)	0.12822 (11)	0.3519 (4)	0.0443 (8)
N2	0.90475 (14)	0.32508 (12)	0.6373 (5)	0.0538 (9)
C7	0.86313 (14)	0.17045 (14)	0.4002 (5)	0.0473 (10)
H7	0.8947	0.1797	0.3969	0.057*
C1	0.84911 (13)	0.20297 (13)	0.4583 (5)	0.0417 (10)
O3	0.94606 (11)	0.33571 (11)	0.6341 (5)	0.0724 (10)
C6	0.80087 (14)	0.18987 (14)	0.4640 (6)	0.0488 (11)
C4	0.82253 (15)	0.26645 (15)	0.5825 (6)	0.0529 (11)
H4	0.8141	0.2879	0.6241	0.063*
C2	0.88280 (14)	0.24797 (13)	0.5163 (6)	0.0452 (10)
H2	0.9143	0.2568	0.5131	0.054*
C3	0.86965 (13)	0.27894 (13)	0.5775 (6)	0.0429 (10)
C13	0.80545 (15)	0.04950 (14)	0.2514 (6)	0.0463 (10)
C10	0.89519 (15)	0.06269 (15)	0.2580 (6)	0.0549 (12)
O2	0.89212 (12)	0.35192 (11)	0.6969 (5)	0.0788 (10)
C11	0.85770 (17)	0.01995 (16)	0.2083 (6)	0.0614 (13)
H11	0.8627	−0.0045	0.1772	0.074*
C5	0.78900 (15)	0.22311 (14)	0.5269 (6)	0.0544 (11)
H5	0.7578	0.2152	0.5303	0.065*
C9	0.88791 (15)	0.09902 (15)	0.3038 (6)	0.0532 (11)
H9	0.9132	0.1278	0.3373	0.064*
C8	0.84359 (13)	0.09318 (13)	0.3005 (5)	0.0424 (10)
C12	0.81262 (16)	0.01297 (14)	0.2039 (6)	0.0568 (12)
H12	0.7876	−0.0159	0.1695	0.068*
C15	0.72262 (15)	0.00229 (14)	0.2147 (6)	0.0630 (13)
H15A	0.6950	0.0048	0.2240	0.094*
H15B	0.7205	−0.0209	0.3011	0.094*
H15C	0.7254	−0.0066	0.0897	0.094*
C14	0.9427 (2)	0.0689 (2)	0.2677 (12)	0.0853 (18)
F1A	0.9456 (8)	0.0369 (9)	0.340 (5)	0.142 (14)	0.39 (2)
F2A	0.9748 (7)	0.1072 (7)	0.317 (7)	0.158 (16)	0.39 (2)
F3A	0.9570 (6)	0.0665 (12)	0.074 (2)	0.152 (9)	0.39 (2)
F1B	0.9474 (5)	0.0345 (4)	0.221 (3)	0.136 (9)	0.61 (2)
F2B	0.9590 (5)	0.0783 (9)	0.4489 (18)	0.156 (7)	0.61 (2)
F3B	0.9727 (4)	0.1064 (6)	0.181 (2)	0.128 (7)	0.61 (2)

	U11	U22	U33	U12	U13	U23
O4	0.0435 (17)	0.0424 (17)	0.077 (2)	0.0155 (15)	0.0007 (15)	−0.0058 (15)
O1	0.0437 (17)	0.048 (2)	0.097 (3)	0.0190 (16)	0.0001 (17)	−0.0140 (17)
N1	0.045 (2)	0.0307 (18)	0.050 (2)	0.0140 (17)	−0.0002 (17)	−0.0023 (15)
N2	0.057 (3)	0.040 (2)	0.059 (2)	0.021 (2)	−0.0016 (19)	−0.0045 (18)
C7	0.040 (2)	0.051 (3)	0.051 (3)	0.024 (2)	0.005 (2)	0.006 (2)
C1	0.036 (2)	0.040 (2)	0.046 (2)	0.017 (2)	0.0036 (18)	0.0010 (19)
O3	0.047 (2)	0.058 (2)	0.100 (3)	0.0173 (17)	−0.0097 (18)	−0.0190 (18)
C6	0.046 (3)	0.035 (2)	0.058 (3)	0.014 (2)	0.005 (2)	−0.002 (2)
C4	0.058 (3)	0.049 (3)	0.061 (3)	0.034 (2)	0.004 (2)	0.001 (2)
C2	0.039 (2)	0.044 (3)	0.051 (3)	0.019 (2)	−0.0017 (19)	−0.0007 (19)
C3	0.043 (3)	0.035 (2)	0.051 (3)	0.020 (2)	−0.0026 (19)	0.0000 (19)
C13	0.047 (3)	0.043 (3)	0.048 (3)	0.021 (2)	0.008 (2)	0.008 (2)
C10	0.051 (3)	0.048 (3)	0.069 (3)	0.027 (2)	0.006 (2)	0.001 (2)
O2	0.081 (2)	0.0451 (19)	0.111 (3)	0.032 (2)	0.003 (2)	−0.0172 (19)
C11	0.065 (3)	0.047 (3)	0.079 (4)	0.033 (3)	0.006 (3)	0.000 (2)
C5	0.041 (3)	0.051 (3)	0.070 (3)	0.022 (2)	0.005 (2)	0.000 (2)
C9	0.049 (3)	0.044 (3)	0.062 (3)	0.020 (2)	0.002 (2)	0.002 (2)
C8	0.044 (3)	0.031 (2)	0.046 (2)	0.014 (2)	0.0038 (19)	0.0014 (18)
C12	0.058 (3)	0.035 (2)	0.071 (3)	0.019 (2)	0.001 (2)	−0.003 (2)
C15	0.046 (3)	0.045 (3)	0.081 (3)	0.010 (2)	−0.008 (2)	−0.009 (2)
C14	0.060 (4)	0.059 (4)	0.135 (7)	0.028 (3)	0.014 (4)	0.006 (4)
F1A	0.095 (10)	0.15 (2)	0.23 (3)	0.094 (15)	0.062 (17)	0.12 (2)
F2A	0.069 (11)	0.075 (12)	0.33 (5)	0.041 (9)	−0.09 (2)	−0.032 (18)
F3A	0.137 (12)	0.20 (2)	0.152 (13)	0.107 (15)	0.075 (9)	0.028 (14)
F1B	0.078 (6)	0.094 (10)	0.26 (2)	0.058 (7)	−0.002 (10)	−0.056 (12)
F2B	0.132 (9)	0.257 (19)	0.150 (9)	0.149 (12)	−0.068 (7)	−0.062 (10)
F3B	0.060 (7)	0.130 (11)	0.194 (15)	0.047 (7)	0.047 (8)	0.054 (12)

O4—C13	1.359 (5)	C13—C8	1.405 (5)
O4—C15	1.439 (4)	C10—C9	1.376 (5)
O1—C6	1.299 (4)	C10—C11	1.380 (6)
O1—H1	0.8200	C10—C14	1.478 (7)
N1—C7	1.295 (5)	C11—C12	1.389 (6)
N1—C8	1.426 (5)	C11—H11	0.9300
N2—O3	1.227 (4)	C5—H5	0.9300
N2—O2	1.230 (4)	C9—C8	1.378 (5)
N2—C3	1.443 (5)	C9—H9	0.9300
C7—C1	1.428 (5)	C12—H12	0.9300
C7—H7	0.9300	C15—H15A	0.9600
C1—C2	1.402 (5)	C15—H15B	0.9600
C1—C6	1.428 (5)	C15—H15C	0.9600
C6—C5	1.411 (5)	C14—F1A	1.225 (17)
C4—C5	1.360 (6)	C14—F2A	1.228 (19)
C4—C3	1.397 (5)	C14—F3A	1.481 (17)
C4—H4	0.9300	C14—F1B	1.267 (12)
C2—C3	1.368 (5)	C14—F3B	1.295 (13)
C2—H2	0.9300	C14—F2B	1.379 (12)
C13—C12	1.383 (5)
C13—O4—C15	117.4 (3)	C12—C11—H11	119.5
C6—O1—H1	109.5	C4—C5—C6	121.0 (4)
C7—N1—C8	124.3 (4)	C4—C5—H5	119.5
O3—N2—O2	122.0 (4)	C6—C5—H5	119.5
O3—N2—C3	119.2 (4)	C10—C9—C8	120.7 (4)
O2—N2—C3	118.8 (4)	C10—C9—H9	119.6
N1—C7—C1	121.0 (4)	C8—C9—H9	119.6
N1—C7—H7	119.5	C9—C8—C13	119.5 (4)
C1—C7—H7	119.5	C9—C8—N1	124.6 (4)
C2—C1—C6	119.1 (4)	C13—C8—N1	115.8 (4)
C2—C1—C7	120.0 (4)	C13—C12—C11	119.1 (4)
C6—C1—C7	120.9 (4)	C13—C12—H12	120.4
O1—C6—C5	119.7 (4)	C11—C12—H12	120.4
O1—C6—C1	121.9 (4)	O4—C15—H15A	109.5
C5—C6—C1	118.4 (4)	O4—C15—H15B	109.5
C5—C4—C3	120.3 (4)	H15A—C15—H15B	109.5
C5—C4—H4	119.9	O4—C15—H15C	109.5
C3—C4—H4	119.9	H15A—C15—H15C	109.5
C3—C2—C1	120.5 (4)	H15B—C15—H15C	109.5
C3—C2—H2	119.8	F1A—C14—F2A	111.5 (16)
C1—C2—H2	119.8	F1A—C14—F3A	100.7 (13)
C2—C3—C4	120.7 (4)	F2A—C14—F3A	100.8 (18)
C2—C3—N2	119.8 (4)	F1B—C14—F3B	110.7 (11)
C4—C3—N2	119.5 (4)	F1B—C14—F2B	103.7 (10)
O4—C13—C12	124.8 (4)	F3B—C14—F2B	102.1 (10)
O4—C13—C8	115.2 (4)	F1A—C14—C10	115.9 (11)
C12—C13—C8	120.0 (4)	F2A—C14—C10	117.9 (11)
C9—C10—C11	119.6 (4)	C10—C14—F3A	107.1 (8)
C9—C10—C14	120.3 (5)	F1B—C14—C10	117.5 (8)
C11—C10—C14	120.1 (5)	F3B—C14—C10	111.3 (8)
C10—C11—C12	121.0 (4)	F2B—C14—C10	110.2 (6)
C10—C11—H11	119.5
C8—N1—C7—C1	−177.0 (3)	C14—C10—C9—C8	−178.1 (5)
N1—C7—C1—C2	177.7 (4)	C10—C9—C8—C13	0.6 (6)
N1—C7—C1—C6	−0.3 (6)	C10—C9—C8—N1	177.7 (4)
C2—C1—C6—O1	180.0 (4)	O4—C13—C8—C9	177.8 (4)
C7—C1—C6—O1	−1.9 (6)	C12—C13—C8—C9	−1.0 (6)
C2—C1—C6—C5	0.5 (6)	O4—C13—C8—N1	0.4 (5)
C7—C1—C6—C5	178.5 (4)	C12—C13—C8—N1	−178.4 (3)
C6—C1—C2—C3	0.0 (6)	C7—N1—C8—C9	3.1 (6)
C7—C1—C2—C3	−178.1 (4)	C7—N1—C8—C13	−179.6 (4)
C1—C2—C3—C4	−0.3 (6)	O4—C13—C12—C11	−177.7 (4)
C1—C2—C3—N2	179.8 (4)	C8—C13—C12—C11	0.9 (6)
C5—C4—C3—C2	0.2 (6)	C10—C11—C12—C13	−0.4 (7)
C5—C4—C3—N2	−179.9 (4)	C9—C10—C14—F1A	136 (2)
O3—N2—C3—C2	−0.7 (6)	C11—C10—C14—F1A	−42 (2)
O2—N2—C3—C2	−177.9 (4)	C9—C10—C14—F2A	0 (3)
O3—N2—C3—C4	179.4 (4)	C11—C10—C14—F2A	−178 (3)
O2—N2—C3—C4	2.2 (6)	C9—C10—C14—F1B	−179.0 (14)
C15—O4—C13—C12	0.5 (6)	C11—C10—C14—F1B	2.9 (16)
C15—O4—C13—C8	−178.3 (4)	C9—C10—C14—F3B	−49.9 (13)
C9—C10—C11—C12	−0.1 (7)	C11—C10—C14—F3B	132.0 (12)
C14—C10—C11—C12	178.0 (5)	C9—C10—C14—F2B	62.5 (13)
C3—C4—C5—C6	0.3 (6)	C11—C10—C14—F2B	−115.5 (12)
O1—C6—C5—C4	179.8 (4)	C9—C10—C14—F3A	−112.9 (16)
C1—C6—C5—C4	−0.6 (6)	C11—C10—C14—F3A	69.1 (16)
C11—C10—C9—C8	0.0 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.84	2.571 (4)	148
O1—H1···O4	0.82	2.76	3.468 (4)	146
C7—H7···O2i	0.93	2.55	3.476 (7)	176
C9—H9···O2i	0.93	2.46	3.378 (6)	169

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1N1	0.82	1.84	2.571(4)	148
O1H1O4	0.82	2.76	3.468(4)	146
C7H7O2i	0.93	2.55	3.476(7)	176
C9H9O2i	0.93	2.46	3.378(6)	169

Symmetry code: (i) .