3-[3-(Trifluoro­meth­yl)phenyl­imino­meth­yl]benzene-1,2-diol

Shuja, S.; Ali, S.; Meetsma, A.; Broker, G.A.; Tiekink, E.R.T.

doi:10.1107/S1600536807011361

3-[3-(Trifluoromethyl)phenyliminomethyl]benzene-1,2-diol

S. Shuja, S. Ali, A. Meetsma, G. A. Broker and E. R. T. Tiekink

The crystal packing of the essentially planar molecules of the title compound, C₁₄H₁₀F₃NO₂, is stabilized by O—H

O hydrogen bonds and possible C—H

O and C—H

F interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011361/hb2320sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011361/hb2320Isup2.hkl Contains datablock I

CCDC reference: 643644

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R factor = 0.046
wR factor = 0.139
Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    F     Ueq(max)/Ueq(min) ...       4.91 Ratio

Author Response: ...The CF~3~ group was found to be disordered with two positions being resolved. Refinement showed the major component (anisotropic) to have a site occupancy = 0.908(4) and the minor component (isotropic) with a site occupancy = 0.092(4).


Alert level C
PLAT213_ALERT_2_C Atom F3      has ADP max/min Ratio .............       3.40 prola
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C1A
PLAT301_ALERT_3_C Main Residue  Disorder .........................      17.00 Perc.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4     ..  O1      ..       2.61 Ang.

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART, (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2006); data reduction: SAINT-Plus; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97.

3-[3-(Trifluoromethyl)phenyliminomethyl]benzene-1,2-diol top

Crystal data top

C₁₄H₁₀F₃NO₂	F(000) = 576
M_r = 281.23	D_x = 1.546 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5078 reflections
a = 16.2463 (9) Å	θ = 2.6–29.5°
b = 4.7716 (3) Å	µ = 0.14 mm⁻¹
c = 16.9199 (9) Å	T = 100 K
β = 112.939 (1)°	Block, orange-red
V = 1207.92 (12) Å³	0.49 × 0.41 × 0.22 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2109 independent reflections
Radiation source: fine-focus sealed tube	1870 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm^-1	θ_max = 25.0°, θ_min = 2.6°
ω scans	h = −19→17
Absorption correction: multi-scan (SADABS; Bruker, 2006)	k = 0→5
T_min = 0.909, T_max = 0.971	l = 0→19
8910 measured reflections

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0781P)² + 0.695P] where P = (F_o² + 2F_c²)/3
2109 reflections	(Δ/σ)_max < 0.001
201 parameters	Δρ_max = 0.49 e Å⁻³
8 restraints	Δρ_min = −0.40 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.82417 (12)	0.3364 (4)	0.39916 (12)	0.0276 (4)	0.908 (4)
F1	0.87946 (12)	0.1499 (4)	0.45002 (11)	0.0580 (6)	0.908 (4)
F2	0.79056 (10)	0.2039 (5)	0.32209 (9)	0.0561 (6)	0.908 (4)
F3	0.87048 (13)	0.5458 (3)	0.38851 (18)	0.0816 (9)	0.908 (4)
C1A	0.82417 (12)	0.3364 (4)	0.39916 (12)	0.0276 (4)	0.092 (4)
F1A	0.8331 (15)	0.077 (2)	0.4117 (10)	0.108 (10)*	0.092 (4)
F2A	0.8099 (7)	0.389 (3)	0.3224 (6)	0.022 (4)*	0.092 (4)
F3A	0.8945 (9)	0.459 (4)	0.4482 (9)	0.062 (6)*	0.092 (4)
O1	0.29573 (8)	1.5909 (2)	0.26882 (8)	0.0247 (3)
H1O	0.2706	1.7440	0.2496	0.037*
O2	0.41465 (8)	1.1978 (3)	0.34631 (8)	0.0251 (3)
H2O	0.4577	1.0850	0.3629	0.038*
N1	0.55754 (9)	0.9236 (3)	0.35995 (9)	0.0214 (3)
C2	0.75077 (11)	0.4256 (4)	0.42676 (11)	0.0227 (4)
C3	0.74251 (11)	0.3013 (4)	0.49780 (11)	0.0243 (4)
H3	0.7834	0.1607	0.5297	0.029*
C4	0.67344 (12)	0.3867 (4)	0.52115 (11)	0.0265 (4)
H4	0.6667	0.3036	0.5693	0.032*
C5	0.61422 (12)	0.5926 (4)	0.47458 (11)	0.0240 (4)
H5	0.5675	0.6501	0.4915	0.029*
C6	0.62212 (11)	0.7168 (3)	0.40319 (11)	0.0204 (4)
C7	0.69145 (11)	0.6307 (4)	0.37922 (11)	0.0219 (4)
H7	0.6979	0.7120	0.3307	0.026*
C8	0.56055 (11)	1.0658 (3)	0.29622 (11)	0.0209 (4)
H8	0.6070	1.0300	0.2767	0.025*
C9	0.49444 (11)	1.2791 (3)	0.25370 (11)	0.0200 (4)
C10	0.50036 (11)	1.4337 (4)	0.18519 (11)	0.0226 (4)
H10	0.5472	1.3949	0.1664	0.027*
C11	0.43910 (12)	1.6407 (4)	0.14509 (11)	0.0231 (4)
H11	0.4439	1.7443	0.0991	0.028*
C12	0.36956 (11)	1.6977 (4)	0.17246 (11)	0.0219 (4)
H12	0.3271	1.8397	0.1448	0.026*
C13	0.36279 (11)	1.5480 (3)	0.23952 (11)	0.0205 (4)
C14	0.42466 (11)	1.3369 (3)	0.28125 (11)	0.0200 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0277 (9)	0.0243 (9)	0.0321 (10)	0.0041 (7)	0.0132 (8)	0.0036 (8)
F1	0.0523 (10)	0.0809 (12)	0.0511 (10)	0.0462 (9)	0.0313 (9)	0.0318 (9)
F2	0.0430 (8)	0.0863 (16)	0.0454 (9)	0.0055 (9)	0.0242 (7)	−0.0207 (8)
F3	0.0755 (13)	0.0296 (8)	0.189 (3)	−0.0035 (8)	0.1056 (16)	0.0007 (11)
C1A	0.0277 (9)	0.0243 (9)	0.0321 (10)	0.0041 (7)	0.0132 (8)	0.0036 (8)
O1	0.0219 (6)	0.0231 (6)	0.0330 (7)	0.0024 (5)	0.0150 (5)	0.0023 (5)
O2	0.0249 (6)	0.0255 (7)	0.0290 (7)	0.0042 (5)	0.0150 (5)	0.0050 (5)
N1	0.0214 (7)	0.0201 (7)	0.0229 (7)	−0.0010 (6)	0.0089 (6)	−0.0022 (6)
C2	0.0212 (8)	0.0214 (8)	0.0240 (9)	−0.0026 (7)	0.0072 (7)	−0.0037 (7)
C3	0.0234 (9)	0.0229 (9)	0.0224 (9)	−0.0001 (7)	0.0043 (7)	0.0005 (7)
C4	0.0290 (9)	0.0295 (9)	0.0202 (9)	−0.0022 (7)	0.0086 (7)	0.0010 (7)
C5	0.0232 (9)	0.0284 (9)	0.0222 (9)	−0.0022 (7)	0.0106 (7)	−0.0036 (7)
C6	0.0194 (8)	0.0192 (8)	0.0209 (8)	−0.0027 (7)	0.0060 (7)	−0.0040 (7)
C7	0.0235 (9)	0.0219 (8)	0.0212 (9)	−0.0021 (7)	0.0097 (7)	−0.0007 (7)
C8	0.0190 (8)	0.0207 (8)	0.0241 (9)	−0.0024 (7)	0.0097 (7)	−0.0046 (7)
C9	0.0191 (8)	0.0193 (8)	0.0208 (8)	−0.0025 (7)	0.0070 (7)	−0.0040 (6)
C10	0.0220 (8)	0.0249 (9)	0.0240 (9)	−0.0034 (7)	0.0123 (7)	−0.0046 (7)
C11	0.0254 (9)	0.0233 (9)	0.0206 (9)	−0.0022 (7)	0.0089 (7)	−0.0007 (7)
C12	0.0205 (8)	0.0192 (8)	0.0227 (9)	−0.0017 (7)	0.0049 (7)	−0.0023 (7)
C13	0.0173 (8)	0.0201 (8)	0.0241 (9)	−0.0031 (7)	0.0081 (7)	−0.0049 (7)
C14	0.0198 (8)	0.0191 (8)	0.0215 (8)	−0.0046 (7)	0.0087 (7)	−0.0033 (7)

Geometric parameters (Å, º) top

C1—F3	1.305 (2)	C3—H3	0.9500
C1—F1	1.318 (2)	C4—C5	1.386 (3)
C1—F2	1.358 (2)	C4—H4	0.9500
C1—C2	1.502 (2)	C5—C6	1.395 (2)
C1A—F1A	1.256 (11)	C5—H5	0.9500
C1A—F2A	1.251 (9)	C6—C7	1.399 (2)
C1A—F3A	1.264 (10)	C7—H7	0.9500
C1A—C2	1.502 (2)	C8—C9	1.451 (2)
F1A—F2A	2.048 (16)	C8—H8	0.9500
O1—C13	1.377 (2)	C9—C10	1.408 (2)
O1—H1O	0.84	C9—C14	1.411 (2)
O2—C14	1.349 (2)	C10—C11	1.378 (2)
O2—H2O	0.84	C10—H10	0.9500
N1—C8	1.291 (2)	C11—C12	1.405 (2)
N1—C6	1.418 (2)	C11—H11	0.9500
C2—C3	1.393 (3)	C12—C13	1.381 (2)
C2—C7	1.389 (2)	C12—H12	0.9500
C3—C4	1.388 (3)	C13—C14	1.403 (2)

F3—C1—F1	108.92 (18)	C6—C5—H5	119.5
F3—C1—F2	105.16 (18)	C5—C6—C7	118.82 (16)
F1—C1—F2	103.26 (17)	C5—C6—N1	116.29 (15)
F3—C1—C2	113.36 (16)	C7—C6—N1	124.88 (15)
F1—C1—C2	114.21 (16)	C2—C7—C6	119.62 (16)
F2—C1—C2	111.09 (15)	C2—C7—H7	120.2
F1A—C1A—F2A	109.5 (6)	C6—C7—H7	120.2
F1A—C1A—F3A	109.3 (6)	N1—C8—C9	121.42 (15)
F2A—C1A—F3A	110.1 (5)	N1—C8—H8	119.3
F1A—C1A—C2	106.3 (10)	C9—C8—H8	119.3
F2A—C1A—C2	114.7 (5)	C10—C9—C14	119.40 (16)
F3A—C1A—C2	106.8 (7)	C10—C9—C8	120.05 (15)
C13—O1—H1O	108.8	C14—C9—C8	120.54 (15)
C14—O2—H2O	103.9	C11—C10—C9	120.83 (16)
C8—N1—C6	122.38 (15)	C11—C10—H10	119.6
C3—C2—C7	121.41 (16)	C9—C10—H10	119.6
C3—C2—C1A	120.20 (16)	C10—C11—C12	119.73 (16)
C7—C2—C1A	118.38 (16)	C10—C11—H11	120.1
C3—C2—C1	120.20 (16)	C12—C11—H11	120.1
C7—C2—C1	118.38 (16)	C13—C12—C11	120.16 (16)
C4—C3—C2	118.76 (16)	C13—C12—H12	119.9
C4—C3—H3	120.6	C11—C12—H12	119.9
C2—C3—H3	120.6	O1—C13—C12	123.12 (15)
C5—C4—C3	120.35 (17)	O1—C13—C14	115.96 (15)
C5—C4—H4	119.8	C12—C13—C14	120.91 (15)
C3—C4—H4	119.8	O2—C14—C13	118.24 (15)
C4—C5—C6	121.04 (16)	O2—C14—C9	122.79 (15)
C4—C5—H5	119.5	C13—C14—C9	118.97 (15)

F3A—C1A—F1A—F2A	−120.7 (9)	C4—C5—C6—C7	−0.2 (3)
C2—C1A—F1A—F2A	124.4 (7)	C4—C5—C6—N1	179.55 (15)
F3A—C1A—F2A—F1A	120.2 (9)	C8—N1—C6—C5	175.80 (15)
C2—C1A—F2A—F1A	−119.3 (11)	C8—N1—C6—C7	−4.4 (3)
F1A—C1A—C2—C3	36.9 (9)	C3—C2—C7—C6	0.5 (3)
F2A—C1A—C2—C3	158.1 (7)	C1A—C2—C7—C6	179.66 (15)
F3A—C1A—C2—C3	−79.7 (8)	C1—C2—C7—C6	179.66 (15)
F1A—C1A—C2—C7	−142.3 (8)	C5—C6—C7—C2	−0.2 (2)
F2A—C1A—C2—C7	−21.1 (7)	N1—C6—C7—C2	−179.99 (15)
F3A—C1A—C2—C7	101.1 (8)	C6—N1—C8—C9	−179.13 (14)
F1A—C1A—C2—C1	0 (100)	N1—C8—C9—C10	179.02 (15)
F2A—C1A—C2—C1	0 (100)	N1—C8—C9—C14	0.0 (2)
F3A—C1A—C2—C1	0 (38)	C14—C9—C10—C11	0.2 (2)
F3—C1—C2—C3	−129.1 (2)	C8—C9—C10—C11	−178.80 (15)
F1—C1—C2—C3	−3.5 (3)	C9—C10—C11—C12	−0.3 (3)
F2—C1—C2—C3	112.7 (2)	C10—C11—C12—C13	0.3 (2)
F3—C1—C2—C7	51.7 (3)	C11—C12—C13—O1	−179.19 (15)
F1—C1—C2—C7	177.24 (17)	C11—C12—C13—C14	−0.1 (2)
F2—C1—C2—C7	−66.5 (2)	O1—C13—C14—O2	−0.9 (2)
F3—C1—C2—C1A	0 (42)	C12—C13—C14—O2	180.00 (14)
F1—C1—C2—C1A	0 (100)	O1—C13—C14—C9	179.13 (14)
F2—C1—C2—C1A	0 (100)	C12—C13—C14—C9	0.0 (2)
C7—C2—C3—C4	−0.2 (3)	C10—C9—C14—O2	179.97 (15)
C1A—C2—C3—C4	−179.42 (16)	C8—C9—C14—O2	−1.0 (2)
C1—C2—C3—C4	−179.42 (16)	C10—C9—C14—C13	0.0 (2)
C2—C3—C4—C5	−0.2 (3)	C8—C9—C14—C13	178.95 (14)
C3—C4—C5—C6	0.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O1ⁱ	0.84	1.93	2.7510 (15)	165
O2—H2O···N1	0.84	1.81	2.596 (2)	154
C10—H10···F3ⁱⁱ	0.95	2.53	3.380 (3)	149
C4—H4···O1ⁱⁱⁱ	0.95	2.61	3.392 (2)	140

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+1, −y+2, −z+1.

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3-[3-(Trifluoro­meth­yl)phenyl­imino­meth­yl]benzene-1,2-diol

Supporting information

Key indicators

checkCIF/PLATON results

3-[3-(Trifluoromethyl)phenyliminomethyl]benzene-1,2-diol