2,2,2-Trifluoro-N-(2-hydr­oxy-5-nitro­phen­yl)acetamide

In the crystal structure of the title compound, C₈H₅F₃N₂O₄, all atoms apart from two F atoms are located on a crystallographic mirror plane. In the mirror plane, the mol­ecules are linked by strong inter­molecular O—H...O hydrogen bonds, forming a chain along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.069
• wR factor = 0.142
• Data-to-parameter ratio = 9.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C8

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.54
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.

2,2,2-Trifluoro-N-(2-hydroxy-5-nitrophenyl)acetamide

Crystal data

C8H5F3N2O4	F(000) = 504
Mr = 250.14	Dx = 1.711 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 1127 reflections
a = 19.7661 (7) Å	θ = 2.9–24.4°
b = 6.610 (9) Å	µ = 0.17 mm^−1
c = 7.4321 (8) Å	T = 298 K
V = 971.0 (13) Å^3	Block, colourless
Z = 4	0.39 × 0.27 × 0.24 mm

Data collection

Bruker APEX area-detector diffractometer	954 independent reflections
Radiation source: fine-focus sealed tube	848 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 25.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
Tmin = 0.936, Tmax = 0.960	k = −5→7
4879 measured reflections	l = −8→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0736P)^2 + 1.1933P] where P = (Fo^2 + 2Fc^2)/3
954 reflections	(Δ/σ)max = 0.001
100 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃): δ 9.12 (1H, NH), 8.64 (s, 1H, OH), 8.04 (d, J = 2.70 Hz, 1H, Ph), 7.26 (s, 1H, Ph), 7.01 (d, J = 2.94, 1H, Ph); ¹³C NMR (acetone-d₆): δ 154.70 (q, J = 45.3 Hz), 147.70, 145.10, 129.74, 121.53, 115.60 (q, J = 271.7 Hz), 115.23, 109.69; IR (KBr press, cm^-1): 3385.3 (ρ_NH), 3191.8 (ρ_OH), 1694.9 (ρ_CO); MS (EI): m/z 251.0 (M + 1, 100).

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.25551 (14)	0.5946 (6)	1.2324 (5)	0.1251 (14)
F2	0.27736 (18)	0.7500	0.9961 (5)	0.129 (2)
O1	0.13859 (18)	0.7500	0.5761 (4)	0.0723 (13)
H1	0.1334	0.7500	0.4702	0.087*
O2	−0.1540 (2)	0.7500	0.8891 (7)	0.1003 (18)
O3	−0.0942 (2)	0.7500	1.1310 (6)	0.0818 (14)
O4	0.12420 (19)	0.7500	1.2184 (4)	0.0727 (14)
N1	−0.0997 (2)	0.7500	0.9669 (8)	0.0628 (13)
N2	0.14742 (19)	0.7500	0.9215 (5)	0.0468 (11)
H2	0.1805	0.7500	0.8462	0.056*
C1	0.0818 (2)	0.7500	0.8483 (6)	0.0410 (11)
C2	0.0785 (3)	0.7500	0.6600 (6)	0.0495 (13)
C3	0.0162 (3)	0.7500	0.5747 (7)	0.0606 (15)
H3	0.0140	0.7500	0.4497	0.073*
C4	−0.0425 (3)	0.7500	0.6745 (8)	0.0611 (15)
H4	−0.0844	0.7500	0.6179	0.073*
C5	−0.0381 (2)	0.7500	0.8589 (7)	0.0479 (12)
C6	0.0230 (2)	0.7500	0.9473 (6)	0.0427 (11)
H6	0.0246	0.7500	1.0724	0.051*
C7	0.1637 (2)	0.7500	1.0940 (6)	0.0458 (12)
C8	0.2394 (3)	0.7500	1.1350 (6)	0.0536 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0754 (18)	0.133 (3)	0.167 (3)	−0.0004 (18)	−0.0430 (19)	0.068 (3)
F2	0.049 (2)	0.275 (7)	0.064 (2)	0.000	0.0005 (18)	0.000
O1	0.057 (2)	0.135 (4)	0.0249 (17)	0.000	0.0020 (15)	0.000
O2	0.041 (2)	0.152 (5)	0.108 (4)	0.000	−0.004 (2)	0.000
O3	0.065 (3)	0.106 (4)	0.074 (3)	0.000	0.025 (2)	0.000
O4	0.054 (2)	0.138 (4)	0.0252 (17)	0.000	0.0024 (16)	0.000
N1	0.045 (3)	0.059 (3)	0.084 (4)	0.000	0.010 (3)	0.000
N2	0.040 (2)	0.075 (3)	0.0248 (18)	0.000	0.0035 (15)	0.000
C1	0.043 (2)	0.051 (3)	0.029 (2)	0.000	−0.0012 (18)	0.000
C2	0.055 (3)	0.063 (3)	0.030 (2)	0.000	−0.002 (2)	0.000
C3	0.063 (3)	0.083 (4)	0.036 (3)	0.000	−0.011 (2)	0.000
C4	0.051 (3)	0.069 (4)	0.064 (3)	0.000	−0.018 (3)	0.000
C5	0.045 (3)	0.047 (3)	0.052 (3)	0.000	0.000 (2)	0.000
C6	0.050 (3)	0.045 (3)	0.032 (2)	0.000	−0.0002 (19)	0.000
C7	0.052 (3)	0.059 (3)	0.026 (2)	0.000	0.002 (2)	0.000
C8	0.053 (3)	0.075 (4)	0.033 (2)	0.000	−0.005 (2)	0.000

Geometric parameters (Å, º)

F1—C8	1.296 (4)	C1—C6	1.376 (6)
F2—C8	1.276 (6)	C1—C2	1.401 (6)
O1—C2	1.341 (6)	C2—C3	1.385 (7)
O1—H1	0.79	C3—C4	1.377 (8)
O2—N1	1.220 (6)	C3—H3	0.93
O3—N1	1.224 (6)	C4—C5	1.373 (7)
O4—C7	1.210 (5)	C4—H4	0.93
N1—C5	1.459 (7)	C5—C6	1.375 (7)
N2—C7	1.322 (6)	C6—H6	0.93
N2—C1	1.406 (6)	C7—C8	1.527 (7)
N2—H2	0.86	C8—F1^i	1.296 (4)
C2—O1—H1	110.3	C5—C4—H4	120.5
O2—N1—O3	123.4 (5)	C3—C4—H4	120.5
O2—N1—C5	118.3 (5)	C4—C5—C6	122.2 (5)
O3—N1—C5	118.3 (5)	C4—C5—N1	119.8 (5)
C7—N2—C1	126.9 (4)	C6—C5—N1	118.1 (4)
C7—N2—H2	116.5	C5—C6—C1	119.1 (4)
C1—N2—H2	116.6	C5—C6—H6	120.4
C6—C1—C2	119.6 (4)	C1—C6—H6	120.4
C6—C1—N2	124.9 (4)	O4—C7—N2	125.7 (5)
C2—C1—N2	115.5 (4)	O4—C7—C8	118.7 (4)
O1—C2—C3	125.1 (4)	N2—C7—C8	115.6 (4)
O1—C2—C1	115.0 (4)	F2—C8—F1^i	107.9 (3)
C3—C2—C1	119.9 (5)	F2—C8—F1	107.9 (3)
C4—C3—C2	120.2 (5)	F1^i—C8—F1	104.9 (5)
C4—C3—H3	119.9	F2—C8—C7	114.5 (4)
C2—C3—H3	119.9	F1^i—C8—C7	110.6 (3)
C5—C4—C3	119.0 (5)	F1—C8—C7	110.6 (3)
O4—C7—C8—F1^i	−57.9 (3)	O4—C7—C8—F1	57.9 (3)
N2—C7—C8—F1^i	122.1 (3)	N2—C7—C8—F1	−122.1 (3)

Symmetry code: (i) x, −y+3/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4^ii	0.79	1.88	2.673 (4)	178
N2—H2···F2	0.86	2.22	2.628 (6)	109
N2—H2···O1	0.86	2.17	2.573 (6)	108
C6—H6···O4	0.93	2.25	2.839 (7)	121

Symmetry code: (ii) x, y, z−1.