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In the title compound, C12H9F3N2O2, the O atoms participate in hydrogen-bonding inter­actions with both the NH group and also the CH groups of adjoining mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050574/gk2038sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050574/gk2038Isup2.hkl
Contains datablock I

CCDC reference: 633854

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in main residue
  • R factor = 0.038
  • wR factor = 0.107
  • Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C31 PLAT431_ALERT_2_B Short Inter HL..A Contact F1B .. F1B .. 2.55 Ang.
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.01 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT301_ALERT_3_C Main Residue Disorder ......................... 14.00 Perc. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C4 - C41 ... 1.44 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C12 H9 F3 N2 O2
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2004); 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, 2003); software used to prepare material for publication: SHELXTL.

N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide top
Crystal data top
C12H9F3N2O2Dx = 1.495 Mg m3
Mr = 270.21Melting point: 422 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.2636 (5) ÅCell parameters from 5756 reflections
b = 11.5179 (6) Åθ = 2.5–26.0°
c = 10.4182 (5) ŵ = 0.13 mm1
β = 102.944 (1)°T = 298 K
V = 1200.29 (10) Å3Block, colorless
Z = 40.48 × 0.37 × 0.18 mm
F(000) = 552
Data collection top
Bruker APEX-2 CCD area-detector
diffractometer
2352 independent reflections
Radiation source: fine-focus sealed tube2043 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
φ and ω scansθmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.914, Tmax = 0.966k = 1414
10248 measured reflectionsl = 1212
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0522P)2 + 0.266P]
where P = (Fo2 + 2Fc2)/3
2352 reflections(Δ/σ)max < 0.001
205 parametersΔρmax = 0.18 e Å3
12 restraintsΔρmin = 0.17 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*/UeqOcc. (<1)
F1A0.0192 (5)1.4133 (7)0.3638 (12)0.112 (2)0.460 (17)
F2A0.1096 (12)1.3882 (7)0.2348 (4)0.097 (2)0.460 (17)
F3A0.1819 (7)1.4534 (5)0.4173 (6)0.0958 (19)0.460 (17)
F1B0.0144 (10)1.4194 (6)0.4202 (12)0.133 (2)0.540 (17)
F2B0.2084 (6)1.4354 (6)0.3930 (8)0.117 (2)0.540 (17)
F3B0.0472 (14)1.3869 (6)0.2308 (3)0.131 (3)0.540 (17)
O10.08946 (12)0.79487 (9)0.35031 (10)0.0640 (3)
O20.04035 (14)0.86410 (10)0.01087 (10)0.0732 (4)
N10.05625 (12)0.96802 (10)0.24202 (11)0.0496 (3)
H1N0.0284 (16)0.9944 (16)0.1659 (17)0.059*
C10.10289 (13)1.04821 (11)0.34244 (12)0.0423 (3)
C110.04782 (13)0.85064 (11)0.25120 (13)0.0443 (3)
C120.02468 (15)0.79203 (12)0.12562 (13)0.0480 (3)
C130.01051 (18)0.66736 (14)0.11129 (18)0.0657 (4)
H13A0.03920.63830.02840.099*
H13B0.01120.62290.18160.099*
H13C0.10450.66090.11470.099*
C140.15676 (17)0.83715 (15)0.06210 (16)0.0664 (5)
H14A0.22160.78310.01280.080*
H14B0.19410.89850.10660.080*
C20.08724 (13)1.16493 (12)0.30784 (13)0.0458 (3)
H2A0.05031.18510.22080.055*
C30.12538 (13)1.25097 (12)0.40009 (13)0.0456 (3)
C310.09872 (14)1.37465 (14)0.35674 (13)0.0639 (4)
C40.18292 (13)1.22119 (13)0.53101 (12)0.0463 (3)
C410.22361 (15)1.30732 (14)0.63252 (14)0.0562 (4)
N410.25692 (16)1.37267 (15)0.71500 (15)0.0784 (5)
C50.20025 (14)1.10469 (13)0.56393 (13)0.0501 (3)
H5A0.23981.08440.65030.060*
C60.16050 (14)1.01818 (12)0.47226 (13)0.0476 (3)
H6A0.17200.94060.49680.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.079 (3)0.075 (2)0.179 (6)0.0299 (18)0.022 (3)0.024 (4)
F2A0.188 (6)0.0500 (18)0.0536 (19)0.006 (3)0.026 (2)0.0110 (19)
F3A0.133 (3)0.0434 (16)0.083 (2)0.013 (2)0.035 (3)0.0116 (16)
F1B0.177 (5)0.080 (2)0.157 (5)0.068 (4)0.069 (4)0.007 (3)
F2B0.135 (3)0.061 (2)0.159 (4)0.039 (2)0.041 (3)0.010 (2)
F3B0.224 (6)0.0482 (17)0.076 (2)0.026 (3)0.058 (3)0.0016 (16)
O10.0831 (8)0.0462 (6)0.0521 (6)0.0027 (5)0.0076 (5)0.0071 (5)
O20.1179 (10)0.0552 (7)0.0396 (5)0.0222 (7)0.0033 (6)0.0006 (5)
N10.0686 (8)0.0392 (6)0.0347 (6)0.0027 (5)0.0014 (5)0.0001 (5)
C10.0461 (7)0.0415 (7)0.0369 (6)0.0022 (5)0.0038 (5)0.0030 (5)
C110.0477 (7)0.0398 (7)0.0434 (7)0.0010 (5)0.0056 (5)0.0006 (5)
C120.0617 (8)0.0393 (7)0.0419 (7)0.0065 (6)0.0090 (6)0.0020 (5)
C130.0790 (11)0.0452 (8)0.0737 (11)0.0031 (7)0.0185 (8)0.0130 (7)
C140.0745 (10)0.0555 (9)0.0568 (9)0.0057 (8)0.0117 (8)0.0029 (7)
C20.0538 (7)0.0429 (7)0.0366 (6)0.0002 (6)0.0014 (5)0.0005 (5)
C30.0479 (7)0.0441 (7)0.0431 (7)0.0015 (6)0.0070 (5)0.0053 (6)
C310.0828 (11)0.0445 (8)0.0587 (9)0.0006 (8)0.0039 (8)0.0081 (7)
C40.0449 (7)0.0532 (8)0.0396 (7)0.0046 (6)0.0070 (5)0.0098 (6)
C410.0584 (8)0.0604 (9)0.0478 (8)0.0061 (7)0.0078 (6)0.0113 (7)
N410.0893 (10)0.0782 (10)0.0625 (9)0.0127 (8)0.0058 (7)0.0298 (8)
C50.0549 (8)0.0570 (9)0.0345 (6)0.0022 (6)0.0017 (5)0.0012 (6)
C60.0548 (7)0.0448 (7)0.0394 (7)0.0000 (6)0.0025 (5)0.0022 (5)
Geometric parameters (Å, º) top
F1A—C311.3071 (16)C12—C131.496 (2)
F2A—C311.3096 (16)C13—H13A0.9600
F3A—C311.3071 (16)C13—H13B0.9600
F1B—C311.3075 (16)C13—H13C0.9600
F2B—C311.3075 (16)C14—H14A0.9700
F3B—C311.3078 (16)C14—H14B0.9700
O1—C111.2098 (16)C2—C31.3749 (18)
O2—C121.4346 (17)C2—H2A0.9300
O2—C141.447 (2)C3—C41.4021 (19)
N1—C111.3595 (18)C3—C311.501 (2)
N1—C11.3972 (16)C4—C51.387 (2)
N1—H1N0.838 (17)C4—C411.4419 (19)
C1—C21.3918 (19)C41—N411.136 (2)
C1—C61.3930 (18)C5—C61.3773 (19)
C11—C121.5116 (18)C5—H5A0.9300
C12—C141.464 (2)C6—H6A0.9300
C12—O2—C1461.07 (10)C3—C2—C1121.12 (12)
C11—N1—C1128.41 (12)C3—C2—H2A119.4
C11—N1—H1N114.4 (12)C1—C2—H2A119.4
C1—N1—H1N117.2 (12)C2—C3—C4119.71 (13)
C2—C1—C6119.38 (12)C2—C3—C31118.01 (11)
C2—C1—N1116.38 (11)C4—C3—C31122.24 (12)
C6—C1—N1124.23 (12)F3A—C31—F1A104.5 (5)
O1—C11—N1124.90 (13)F1B—C31—F2B105.5 (4)
O1—C11—C12120.86 (12)F1B—C31—F3B107.5 (4)
N1—C11—C12114.20 (11)F2B—C31—F3B111.1 (5)
O2—C12—C1459.89 (10)F3A—C31—F2A101.4 (4)
O2—C12—C13117.17 (13)F1A—C31—F2A107.1 (4)
C14—C12—C13121.01 (13)F3A—C31—C3117.3 (3)
O2—C12—C11113.86 (11)F1A—C31—C3114.5 (4)
C14—C12—C11117.33 (12)F1B—C31—C3108.6 (3)
C13—C12—C11115.59 (13)F2B—C31—C3109.5 (3)
C12—C13—H13A109.5F3B—C31—C3114.2 (3)
C12—C13—H13B109.5F2A—C31—C3110.9 (4)
H13A—C13—H13B109.5C5—C4—C3118.69 (12)
C12—C13—H13C109.5C5—C4—C41118.97 (12)
H13A—C13—H13C109.5C3—C4—C41122.33 (13)
H13B—C13—H13C109.5N41—C41—C4178.03 (18)
O2—C14—C1259.04 (10)C6—C5—C4121.80 (12)
O2—C14—H14A117.9C6—C5—H5A119.1
C12—C14—H14A117.9C4—C5—H5A119.1
O2—C14—H14B117.9C5—C6—C1119.28 (13)
C12—C14—H14B117.9C5—C6—H6A120.4
H14A—C14—H14B115.0C1—C6—H6A120.4
C11—N1—C1—C2173.36 (14)C2—C3—C31—F1A87.7 (6)
C11—N1—C1—C65.5 (2)C4—C3—C31—F1A90.1 (6)
C1—N1—C11—O15.5 (2)C2—C3—C31—F1B116.3 (7)
C1—N1—C11—C12172.25 (13)C4—C3—C31—F1B61.4 (7)
C14—O2—C12—C13111.83 (16)C2—C3—C31—F2B128.9 (5)
C14—O2—C12—C11108.90 (14)C4—C3—C31—F2B53.3 (5)
O1—C11—C12—O2166.44 (13)C2—C3—C31—F3B3.6 (7)
N1—C11—C12—O215.75 (18)C4—C3—C31—F3B178.7 (7)
O1—C11—C12—C14126.44 (16)C2—C3—C31—F2A33.7 (6)
N1—C11—C12—C1451.37 (17)C4—C3—C31—F2A148.6 (6)
O1—C11—C12—C1326.5 (2)C2—C3—C4—C50.2 (2)
N1—C11—C12—C13155.69 (13)C31—C3—C4—C5177.90 (13)
C13—C12—C14—O2105.50 (15)C2—C3—C4—C41179.30 (13)
C11—C12—C14—O2103.10 (13)C31—C3—C4—C411.6 (2)
C6—C1—C2—C31.2 (2)C3—C4—C5—C61.1 (2)
N1—C1—C2—C3177.70 (12)C41—C4—C5—C6178.40 (13)
C1—C2—C3—C41.0 (2)C4—C5—C6—C10.9 (2)
C1—C2—C3—C31176.84 (12)C2—C1—C6—C50.3 (2)
C2—C3—C31—F3A149.4 (5)N1—C1—C6—C5178.52 (13)
C4—C3—C31—F3A32.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.84 (2)2.48 (2)3.243 (2)151 (1)
C2—H2A···O2i0.932.463.264 (2)145
C14—H14A···O1ii0.972.443.375 (2)161
C6—H6A···O10.932.302.889 (2)121
N1—H1N···O20.84 (2)2.20 (2)2.673 (2)116 (2)
Symmetry codes: (i) x, y+2, z; (ii) x1/2, y+3/2, z1/2.
 

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