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In the mol­ecule of the title compound, C11H11F4NO2, the amide plane is oriented with respect to the planar aromatic ring at a dihedral angle of 19.5 (3)°. In the crystal structure, the mol­ecules are linked firstly into centrosymmetric dimers, and then into infinite chains by inter­molecular N—H...O and O—H...O hydrogen bonds, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807010422/hk2195sup1.cif
Contains datablocks global, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807010422/hk21953sup2.hkl
Contains datablock 3

CCDC reference: 643032

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.046
  • wR factor = 0.138
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C6 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 C4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
0 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 1 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 0 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

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

5,5,5-Trifluoro-N-(4-fluorophenyl)-4-hydroxypentanamide top
Crystal data top
C11H11F4NO2F(000) = 1088
Mr = 265.21Dx = 1.457 Mg m3
Orthorhombic, PccnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2acCell parameters from 3340 reflections
a = 12.162 (2) Åθ = 3.0–22.8°
b = 23.153 (4) ŵ = 0.14 mm1
c = 8.5893 (14) ÅT = 273 K
V = 2418.6 (7) Å3Plate, colorless
Z = 80.30 × 0.30 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2142 independent reflections
Radiation source: fine-focus sealed tube1557 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
φ and ω scansθmax = 25.1°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.959, Tmax = 0.973k = 2627
11531 measured reflectionsl = 910
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0713P)2 + 0.6158P]
where P = (Fo2 + 2Fc2)/3
2142 reflections(Δ/σ)max < 0.001
164 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.18 e Å3
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
xyzUiso*/Ueq
F10.63780 (17)0.70671 (9)0.1727 (3)0.1277 (8)
F20.61515 (15)0.30221 (6)1.15861 (19)0.0931 (6)
F30.75984 (14)0.33225 (6)1.0436 (2)0.0853 (5)
F40.63064 (16)0.29254 (6)0.9123 (2)0.0948 (6)
C10.6219 (2)0.66753 (12)0.2882 (4)0.0785 (8)
C20.6686 (2)0.61488 (13)0.2745 (3)0.0788 (8)
H20.71230.60610.18890.095*
C30.6503 (2)0.57403 (11)0.3904 (3)0.0661 (7)
H30.68150.53750.38230.079*
C40.58628 (16)0.58767 (9)0.5167 (2)0.0477 (5)
C50.5374 (3)0.64079 (11)0.5245 (3)0.0782 (8)
H50.49150.64960.60770.094*
C60.5557 (3)0.68140 (13)0.4096 (4)0.0992 (11)
H60.52310.71770.41530.119*
C70.62436 (16)0.50256 (9)0.6833 (2)0.0459 (5)
C80.58733 (17)0.47352 (10)0.8314 (2)0.0527 (6)
H8A0.50810.46890.82820.063*
H8B0.60460.49850.91880.063*
C90.63946 (18)0.41523 (9)0.8586 (2)0.0510 (5)
H9A0.71850.41990.86610.061*
H9B0.62430.39050.77010.061*
C100.59759 (16)0.38628 (9)1.0057 (2)0.0478 (5)
H100.51850.37980.99290.057*
C110.6512 (2)0.32834 (10)1.0299 (3)0.0631 (6)
N10.56458 (14)0.54842 (7)0.64051 (19)0.0492 (5)
H10.50620.55500.69410.059*
O10.70526 (13)0.48602 (7)0.61034 (18)0.0625 (5)
O20.61248 (11)0.42015 (6)1.14061 (15)0.0481 (4)
H2A0.67260.43611.13690.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.1440 (18)0.1167 (15)0.1223 (17)0.0071 (12)0.0210 (13)0.0743 (13)
F20.1434 (15)0.0641 (9)0.0717 (11)0.0028 (9)0.0173 (10)0.0229 (8)
F30.0802 (11)0.0773 (10)0.0984 (12)0.0211 (8)0.0022 (9)0.0075 (9)
F40.1505 (16)0.0578 (9)0.0760 (11)0.0014 (9)0.0061 (10)0.0147 (8)
C10.0839 (18)0.0773 (18)0.0743 (19)0.0004 (14)0.0005 (15)0.0343 (15)
C20.0689 (16)0.106 (2)0.0617 (17)0.0192 (15)0.0166 (13)0.0317 (15)
C30.0709 (15)0.0748 (16)0.0527 (14)0.0231 (12)0.0137 (12)0.0160 (12)
C40.0479 (11)0.0579 (12)0.0373 (11)0.0060 (9)0.0032 (9)0.0035 (9)
C50.105 (2)0.0727 (17)0.0573 (16)0.0317 (15)0.0156 (14)0.0107 (13)
C60.144 (3)0.0655 (17)0.088 (2)0.0328 (18)0.012 (2)0.0188 (16)
C70.0472 (11)0.0538 (12)0.0366 (11)0.0057 (9)0.0006 (9)0.0011 (9)
C80.0546 (12)0.0636 (13)0.0398 (12)0.0072 (10)0.0042 (9)0.0071 (10)
C90.0629 (13)0.0525 (12)0.0377 (11)0.0017 (10)0.0039 (9)0.0010 (9)
C100.0503 (12)0.0523 (12)0.0407 (11)0.0058 (9)0.0002 (9)0.0005 (9)
C110.0847 (18)0.0517 (13)0.0529 (15)0.0053 (12)0.0039 (12)0.0034 (11)
N10.0494 (10)0.0597 (11)0.0386 (10)0.0107 (8)0.0067 (7)0.0055 (8)
O10.0647 (10)0.0738 (10)0.0491 (9)0.0247 (8)0.0150 (8)0.0135 (8)
O20.0488 (8)0.0574 (9)0.0380 (8)0.0041 (6)0.0051 (6)0.0001 (6)
Geometric parameters (Å, º) top
F1—C11.358 (3)C7—O11.228 (2)
F2—C111.334 (3)C7—N11.339 (3)
F3—C111.330 (3)C7—C81.507 (3)
F4—C111.330 (3)C8—C91.509 (3)
C1—C21.350 (4)C8—H8A0.9700
C1—C61.356 (4)C8—H8B0.9700
C2—C31.391 (3)C9—C101.518 (3)
C2—H20.9300C9—H9A0.9700
C3—C41.372 (3)C9—H9B0.9700
C3—H30.9300C10—O21.411 (2)
C4—C51.368 (3)C10—C111.506 (3)
C4—N11.424 (3)C10—H100.9800
C5—C61.381 (4)N1—H10.8600
C5—H50.9300O2—H2A0.8200
C6—H60.9300
C2—C1—C6122.0 (2)C9—C8—H8B108.8
C2—C1—F1118.7 (3)H8A—C8—H8B107.7
C6—C1—F1119.2 (3)C8—C9—C10112.50 (17)
C1—C2—C3119.0 (2)C8—C9—H9A109.1
C1—C2—H2120.5C10—C9—H9A109.1
C3—C2—H2120.5C8—C9—H9B109.1
C4—C3—C2120.0 (2)C10—C9—H9B109.1
C4—C3—H3120.0H9A—C9—H9B107.8
C2—C3—H3120.0O2—C10—C11109.04 (17)
C5—C4—C3119.5 (2)O2—C10—C9113.27 (16)
C5—C4—N1117.16 (19)C11—C10—C9111.29 (18)
C3—C4—N1123.29 (19)O2—C10—H10107.7
C4—C5—C6120.5 (3)C11—C10—H10107.7
C4—C5—H5119.8C9—C10—H10107.7
C6—C5—H5119.8F3—C11—F4107.2 (2)
C1—C6—C5118.9 (3)F3—C11—F2106.5 (2)
C1—C6—H6120.5F4—C11—F2106.57 (19)
C5—C6—H6120.5F3—C11—C10112.43 (19)
O1—C7—N1122.84 (19)F4—C11—C10111.7 (2)
O1—C7—C8122.08 (18)F2—C11—C10112.1 (2)
N1—C7—C8115.05 (18)C7—N1—C4127.66 (17)
C7—C8—C9113.83 (18)C7—N1—H1116.2
C7—C8—H8A108.8C4—N1—H1116.2
C9—C8—H8A108.8C10—O2—H2A109.5
C7—C8—H8B108.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.102.950 (2)167
O2—H2A···O1ii0.821.902.703 (2)168
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+3/2, y, z+1/2.
 

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