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
CCDC reference: 633854
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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
C12H9F3N2O2 | Dx = 1.495 Mg m−3 |
Mr = 270.21 | Melting point: 422 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2636 (5) Å | Cell parameters from 5756 reflections |
b = 11.5179 (6) Å | θ = 2.5–26.0° |
c = 10.4182 (5) Å | µ = 0.13 mm−1 |
β = 102.944 (1)° | T = 298 K |
V = 1200.29 (10) Å3 | Block, colorless |
Z = 4 | 0.48 × 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 tube | 2043 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
φ and ω scans | θmax = 26.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.914, Tmax = 0.966 | k = −14→14 |
10248 measured reflections | l = −12→12 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H 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 parameters | Δρmax = 0.18 e Å−3 |
12 restraints | Δρmin = −0.17 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 | Uiso*/Ueq | Occ. (<1) |
F1A | −0.0192 (5) | 1.4133 (7) | 0.3638 (12) | 0.112 (2) | 0.460 (17) |
F2A | 0.1096 (12) | 1.3882 (7) | 0.2348 (4) | 0.097 (2) | 0.460 (17) |
F3A | 0.1819 (7) | 1.4534 (5) | 0.4173 (6) | 0.0958 (19) | 0.460 (17) |
F1B | 0.0144 (10) | 1.4194 (6) | 0.4202 (12) | 0.133 (2) | 0.540 (17) |
F2B | 0.2084 (6) | 1.4354 (6) | 0.3930 (8) | 0.117 (2) | 0.540 (17) |
F3B | 0.0472 (14) | 1.3869 (6) | 0.2308 (3) | 0.131 (3) | 0.540 (17) |
O1 | 0.08946 (12) | 0.79487 (9) | 0.35031 (10) | 0.0640 (3) | |
O2 | −0.04035 (14) | 0.86410 (10) | 0.01087 (10) | 0.0732 (4) | |
N1 | 0.05625 (12) | 0.96802 (10) | 0.24202 (11) | 0.0496 (3) | |
H1N | 0.0284 (16) | 0.9944 (16) | 0.1659 (17) | 0.059* | |
C1 | 0.10289 (13) | 1.04821 (11) | 0.34244 (12) | 0.0423 (3) | |
C11 | 0.04782 (13) | 0.85064 (11) | 0.25120 (13) | 0.0443 (3) | |
C12 | −0.02468 (15) | 0.79203 (12) | 0.12562 (13) | 0.0480 (3) | |
C13 | 0.01051 (18) | 0.66736 (14) | 0.11129 (18) | 0.0657 (4) | |
H13A | −0.0392 | 0.6383 | 0.0284 | 0.099* | |
H13B | −0.0112 | 0.6229 | 0.1816 | 0.099* | |
H13C | 0.1045 | 0.6609 | 0.1147 | 0.099* | |
C14 | −0.15676 (17) | 0.83715 (15) | 0.06210 (16) | 0.0664 (5) | |
H14A | −0.2216 | 0.7831 | 0.0128 | 0.080* | |
H14B | −0.1941 | 0.8985 | 0.1066 | 0.080* | |
C2 | 0.08724 (13) | 1.16493 (12) | 0.30784 (13) | 0.0458 (3) | |
H2A | 0.0503 | 1.1851 | 0.2208 | 0.055* | |
C3 | 0.12538 (13) | 1.25097 (12) | 0.40009 (13) | 0.0456 (3) | |
C31 | 0.09872 (14) | 1.37465 (14) | 0.35674 (13) | 0.0639 (4) | |
C4 | 0.18292 (13) | 1.22119 (13) | 0.53101 (12) | 0.0463 (3) | |
C41 | 0.22361 (15) | 1.30732 (14) | 0.63252 (14) | 0.0562 (4) | |
N41 | 0.25692 (16) | 1.37267 (15) | 0.71500 (15) | 0.0784 (5) | |
C5 | 0.20025 (14) | 1.10469 (13) | 0.56393 (13) | 0.0501 (3) | |
H5A | 0.2398 | 1.0844 | 0.6503 | 0.060* | |
C6 | 0.16050 (14) | 1.01818 (12) | 0.47226 (13) | 0.0476 (3) | |
H6A | 0.1720 | 0.9406 | 0.4968 | 0.057* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1A | 0.079 (3) | 0.075 (2) | 0.179 (6) | 0.0299 (18) | 0.022 (3) | 0.024 (4) |
F2A | 0.188 (6) | 0.0500 (18) | 0.0536 (19) | 0.006 (3) | 0.026 (2) | 0.0110 (19) |
F3A | 0.133 (3) | 0.0434 (16) | 0.083 (2) | −0.013 (2) | −0.035 (3) | −0.0116 (16) |
F1B | 0.177 (5) | 0.080 (2) | 0.157 (5) | 0.068 (4) | 0.069 (4) | 0.007 (3) |
F2B | 0.135 (3) | 0.061 (2) | 0.159 (4) | −0.039 (2) | 0.041 (3) | 0.010 (2) |
F3B | 0.224 (6) | 0.0482 (17) | 0.076 (2) | 0.026 (3) | −0.058 (3) | −0.0016 (16) |
O1 | 0.0831 (8) | 0.0462 (6) | 0.0521 (6) | 0.0027 (5) | −0.0076 (5) | 0.0071 (5) |
O2 | 0.1179 (10) | 0.0552 (7) | 0.0396 (5) | −0.0222 (7) | 0.0033 (6) | 0.0006 (5) |
N1 | 0.0686 (8) | 0.0392 (6) | 0.0347 (6) | −0.0027 (5) | −0.0014 (5) | 0.0001 (5) |
C1 | 0.0461 (7) | 0.0415 (7) | 0.0369 (6) | −0.0022 (5) | 0.0038 (5) | −0.0030 (5) |
C11 | 0.0477 (7) | 0.0398 (7) | 0.0434 (7) | 0.0010 (5) | 0.0056 (5) | 0.0006 (5) |
C12 | 0.0617 (8) | 0.0393 (7) | 0.0419 (7) | −0.0065 (6) | 0.0090 (6) | −0.0020 (5) |
C13 | 0.0790 (11) | 0.0452 (8) | 0.0737 (11) | −0.0031 (7) | 0.0185 (8) | −0.0130 (7) |
C14 | 0.0745 (10) | 0.0555 (9) | 0.0568 (9) | −0.0057 (8) | −0.0117 (8) | −0.0029 (7) |
C2 | 0.0538 (7) | 0.0429 (7) | 0.0366 (6) | 0.0002 (6) | 0.0014 (5) | −0.0005 (5) |
C3 | 0.0479 (7) | 0.0441 (7) | 0.0431 (7) | −0.0015 (6) | 0.0070 (5) | −0.0053 (6) |
C31 | 0.0828 (11) | 0.0445 (8) | 0.0587 (9) | −0.0006 (8) | 0.0039 (8) | −0.0081 (7) |
C4 | 0.0449 (7) | 0.0532 (8) | 0.0396 (7) | −0.0046 (6) | 0.0070 (5) | −0.0098 (6) |
C41 | 0.0584 (8) | 0.0604 (9) | 0.0478 (8) | −0.0061 (7) | 0.0078 (6) | −0.0113 (7) |
N41 | 0.0893 (10) | 0.0782 (10) | 0.0625 (9) | −0.0127 (8) | 0.0058 (7) | −0.0298 (8) |
C5 | 0.0549 (8) | 0.0570 (9) | 0.0345 (6) | −0.0022 (6) | 0.0017 (5) | −0.0012 (6) |
C6 | 0.0548 (7) | 0.0448 (7) | 0.0394 (7) | 0.0000 (6) | 0.0025 (5) | 0.0022 (5) |
Geometric parameters (Å, º) top
F1A—C31 | 1.3071 (16) | C12—C13 | 1.496 (2) |
F2A—C31 | 1.3096 (16) | C13—H13A | 0.9600 |
F3A—C31 | 1.3071 (16) | C13—H13B | 0.9600 |
F1B—C31 | 1.3075 (16) | C13—H13C | 0.9600 |
F2B—C31 | 1.3075 (16) | C14—H14A | 0.9700 |
F3B—C31 | 1.3078 (16) | C14—H14B | 0.9700 |
O1—C11 | 1.2098 (16) | C2—C3 | 1.3749 (18) |
O2—C12 | 1.4346 (17) | C2—H2A | 0.9300 |
O2—C14 | 1.447 (2) | C3—C4 | 1.4021 (19) |
N1—C11 | 1.3595 (18) | C3—C31 | 1.501 (2) |
N1—C1 | 1.3972 (16) | C4—C5 | 1.387 (2) |
N1—H1N | 0.838 (17) | C4—C41 | 1.4419 (19) |
C1—C2 | 1.3918 (19) | C41—N41 | 1.136 (2) |
C1—C6 | 1.3930 (18) | C5—C6 | 1.3773 (19) |
C11—C12 | 1.5116 (18) | C5—H5A | 0.9300 |
C12—C14 | 1.464 (2) | C6—H6A | 0.9300 |
| | | |
C12—O2—C14 | 61.07 (10) | C3—C2—C1 | 121.12 (12) |
C11—N1—C1 | 128.41 (12) | C3—C2—H2A | 119.4 |
C11—N1—H1N | 114.4 (12) | C1—C2—H2A | 119.4 |
C1—N1—H1N | 117.2 (12) | C2—C3—C4 | 119.71 (13) |
C2—C1—C6 | 119.38 (12) | C2—C3—C31 | 118.01 (11) |
C2—C1—N1 | 116.38 (11) | C4—C3—C31 | 122.24 (12) |
C6—C1—N1 | 124.23 (12) | F3A—C31—F1A | 104.5 (5) |
O1—C11—N1 | 124.90 (13) | F1B—C31—F2B | 105.5 (4) |
O1—C11—C12 | 120.86 (12) | F1B—C31—F3B | 107.5 (4) |
N1—C11—C12 | 114.20 (11) | F2B—C31—F3B | 111.1 (5) |
O2—C12—C14 | 59.89 (10) | F3A—C31—F2A | 101.4 (4) |
O2—C12—C13 | 117.17 (13) | F1A—C31—F2A | 107.1 (4) |
C14—C12—C13 | 121.01 (13) | F3A—C31—C3 | 117.3 (3) |
O2—C12—C11 | 113.86 (11) | F1A—C31—C3 | 114.5 (4) |
C14—C12—C11 | 117.33 (12) | F1B—C31—C3 | 108.6 (3) |
C13—C12—C11 | 115.59 (13) | F2B—C31—C3 | 109.5 (3) |
C12—C13—H13A | 109.5 | F3B—C31—C3 | 114.2 (3) |
C12—C13—H13B | 109.5 | F2A—C31—C3 | 110.9 (4) |
H13A—C13—H13B | 109.5 | C5—C4—C3 | 118.69 (12) |
C12—C13—H13C | 109.5 | C5—C4—C41 | 118.97 (12) |
H13A—C13—H13C | 109.5 | C3—C4—C41 | 122.33 (13) |
H13B—C13—H13C | 109.5 | N41—C41—C4 | 178.03 (18) |
O2—C14—C12 | 59.04 (10) | C6—C5—C4 | 121.80 (12) |
O2—C14—H14A | 117.9 | C6—C5—H5A | 119.1 |
C12—C14—H14A | 117.9 | C4—C5—H5A | 119.1 |
O2—C14—H14B | 117.9 | C5—C6—C1 | 119.28 (13) |
C12—C14—H14B | 117.9 | C5—C6—H6A | 120.4 |
H14A—C14—H14B | 115.0 | C1—C6—H6A | 120.4 |
| | | |
C11—N1—C1—C2 | −173.36 (14) | C2—C3—C31—F1A | 87.7 (6) |
C11—N1—C1—C6 | 5.5 (2) | C4—C3—C31—F1A | −90.1 (6) |
C1—N1—C11—O1 | −5.5 (2) | C2—C3—C31—F1B | 116.3 (7) |
C1—N1—C11—C12 | 172.25 (13) | C4—C3—C31—F1B | −61.4 (7) |
C14—O2—C12—C13 | 111.83 (16) | C2—C3—C31—F2B | −128.9 (5) |
C14—O2—C12—C11 | −108.90 (14) | C4—C3—C31—F2B | 53.3 (5) |
O1—C11—C12—O2 | −166.44 (13) | C2—C3—C31—F3B | −3.6 (7) |
N1—C11—C12—O2 | 15.75 (18) | C4—C3—C31—F3B | 178.7 (7) |
O1—C11—C12—C14 | 126.44 (16) | C2—C3—C31—F2A | −33.7 (6) |
N1—C11—C12—C14 | −51.37 (17) | C4—C3—C31—F2A | 148.6 (6) |
O1—C11—C12—C13 | −26.5 (2) | C2—C3—C4—C5 | 0.2 (2) |
N1—C11—C12—C13 | 155.69 (13) | C31—C3—C4—C5 | 177.90 (13) |
C13—C12—C14—O2 | −105.50 (15) | C2—C3—C4—C41 | −179.30 (13) |
C11—C12—C14—O2 | 103.10 (13) | C31—C3—C4—C41 | −1.6 (2) |
C6—C1—C2—C3 | −1.2 (2) | C3—C4—C5—C6 | −1.1 (2) |
N1—C1—C2—C3 | 177.70 (12) | C41—C4—C5—C6 | 178.40 (13) |
C1—C2—C3—C4 | 1.0 (2) | C4—C5—C6—C1 | 0.9 (2) |
C1—C2—C3—C31 | −176.84 (12) | C2—C1—C6—C5 | 0.3 (2) |
C2—C3—C31—F3A | −149.4 (5) | N1—C1—C6—C5 | −178.52 (13) |
C4—C3—C31—F3A | 32.9 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.84 (2) | 2.48 (2) | 3.243 (2) | 151 (1) |
C2—H2A···O2i | 0.93 | 2.46 | 3.264 (2) | 145 |
C14—H14A···O1ii | 0.97 | 2.44 | 3.375 (2) | 161 |
C6—H6A···O1 | 0.93 | 2.30 | 2.889 (2) | 121 |
N1—H1N···O2 | 0.84 (2) | 2.20 (2) | 2.673 (2) | 116 (2) |
Symmetry codes: (i) −x, −y+2, −z; (ii) x−1/2, −y+3/2, z−1/2. |