Crystals of the title compound, C
15H
10F
3NO
3, are stabilized by N—H
O and C—H
O intermolecular hydrogen bonds and by weak C—H
π interactions. In the structure, paired C—H
O hydrogen bonds link the molecules into
R22(10) dimers. The hydrogen-bonded
R22(10) dimers are linked by intermolecular N—H
O hydrogen bonds and generate
R64(22) rings. The phthalide section of the molecule is planar and the dihedral angle between the phthalide group and the benzene ring is 56.31 (17)°.
Supporting information
CCDC reference: 620633
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.005 Å
- R factor = 0.071
- wR factor = 0.198
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C17
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.104
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.61 mm
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
4 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 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
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
3-[3-(trifluoromethyl)anilino]isobenzofuran-1(3
H)-one
top
Crystal data top
C15H10F3NO2 | F(000) = 600 |
Mr = 293.24 | Dx = 1.454 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 17541 reflections |
a = 13.4659 (9) Å | θ = 2.5–27.9° |
b = 8.1794 (7) Å | µ = 0.13 mm−1 |
c = 12.2649 (8) Å | T = 296 K |
β = 97.400 (5)° | Prism, colourless |
V = 1339.64 (17) Å3 | 0.61 × 0.42 × 0.12 mm |
Z = 4 | |
Data collection top
Stoe IPDS-2 diffractometer | 2629 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1933 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.104 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.9° |
ω scans | h = −16→16 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −10→10 |
Tmin = 0.942, Tmax = 0.986 | l = −15→15 |
14507 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.071 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.198 | w = 1/[σ2(Fo2) + (0.0685P)2 + 1.3237P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
2629 reflections | Δρmax = 0.40 e Å−3 |
195 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.011 (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 | |
C1 | 0.4651 (2) | 0.6847 (4) | 0.5535 (2) | 0.0536 (8) | |
C2 | 0.3799 (2) | 0.6302 (4) | 0.6071 (2) | 0.0505 (7) | |
C3 | 0.2793 (3) | 0.6569 (5) | 0.5783 (3) | 0.0669 (9) | |
H3 | 0.2558 | 0.7167 | 0.5158 | 0.080* | |
C4 | 0.2147 (3) | 0.5927 (5) | 0.6446 (4) | 0.0790 (11) | |
H4 | 0.1460 | 0.6071 | 0.6264 | 0.095* | |
C5 | 0.2509 (3) | 0.5062 (5) | 0.7386 (4) | 0.0767 (11) | |
H5 | 0.2057 | 0.4647 | 0.7829 | 0.092* | |
C6 | 0.3518 (3) | 0.4799 (4) | 0.7685 (3) | 0.0651 (9) | |
H6 | 0.3756 | 0.4227 | 0.8321 | 0.078* | |
C7 | 0.4164 (2) | 0.5426 (4) | 0.6996 (2) | 0.0485 (7) | |
C8 | 0.5282 (2) | 0.5295 (4) | 0.7071 (2) | 0.0501 (7) | |
H8 | 0.5470 | 0.4156 | 0.6961 | 0.060* | |
C9 | 0.6829 (2) | 0.5818 (4) | 0.8321 (3) | 0.0555 (8) | |
C10 | 0.7451 (2) | 0.5205 (4) | 0.7605 (3) | 0.0596 (8) | |
H10 | 0.7181 | 0.4814 | 0.6919 | 0.071* | |
C11 | 0.8480 (3) | 0.5174 (5) | 0.7913 (3) | 0.0661 (9) | |
C12 | 0.8895 (3) | 0.5753 (6) | 0.8923 (4) | 0.0853 (13) | |
H12 | 0.9585 | 0.5726 | 0.9126 | 0.102* | |
C13 | 0.8272 (3) | 0.6371 (6) | 0.9628 (3) | 0.0916 (14) | |
H13 | 0.8547 | 0.6779 | 1.0308 | 0.110* | |
C14 | 0.7248 (3) | 0.6396 (5) | 0.9344 (3) | 0.0758 (11) | |
H14 | 0.6837 | 0.6799 | 0.9836 | 0.091* | |
C17 | 0.9143 (3) | 0.4546 (6) | 0.7146 (4) | 0.0821 (12) | |
N1 | 0.5792 (2) | 0.5875 (4) | 0.8054 (2) | 0.0597 (8) | |
O1 | 0.4650 (2) | 0.7651 (3) | 0.47137 (19) | 0.0746 (8) | |
O2 | 0.55034 (16) | 0.6305 (3) | 0.61130 (17) | 0.0569 (6) | |
F1 | 1.0044 (2) | 0.4178 (6) | 0.7574 (3) | 0.1586 (17) | |
F2 | 0.9248 (3) | 0.5546 (5) | 0.6336 (4) | 0.1750 (19) | |
F3 | 0.8808 (2) | 0.3188 (5) | 0.6614 (3) | 0.1260 (12) | |
H1 | 0.550 (3) | 0.631 (5) | 0.853 (3) | 0.070 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0604 (19) | 0.0569 (18) | 0.0447 (16) | −0.0063 (14) | 0.0117 (14) | −0.0053 (15) |
C2 | 0.0520 (17) | 0.0521 (17) | 0.0488 (16) | −0.0023 (13) | 0.0120 (13) | −0.0048 (14) |
C3 | 0.059 (2) | 0.074 (2) | 0.067 (2) | 0.0043 (17) | 0.0049 (17) | −0.0022 (18) |
C4 | 0.050 (2) | 0.089 (3) | 0.100 (3) | 0.0007 (18) | 0.015 (2) | −0.004 (2) |
C5 | 0.060 (2) | 0.080 (3) | 0.096 (3) | −0.0032 (18) | 0.036 (2) | 0.008 (2) |
C6 | 0.064 (2) | 0.065 (2) | 0.071 (2) | 0.0014 (16) | 0.0273 (17) | 0.0137 (17) |
C7 | 0.0491 (16) | 0.0482 (16) | 0.0500 (16) | 0.0018 (13) | 0.0137 (13) | −0.0049 (14) |
C8 | 0.0496 (17) | 0.0557 (17) | 0.0475 (16) | 0.0000 (13) | 0.0151 (13) | −0.0025 (14) |
C9 | 0.0563 (18) | 0.0586 (19) | 0.0507 (17) | 0.0035 (14) | 0.0036 (14) | 0.0061 (15) |
C10 | 0.0520 (18) | 0.068 (2) | 0.0585 (19) | 0.0015 (15) | 0.0054 (15) | 0.0040 (16) |
C11 | 0.0523 (19) | 0.075 (2) | 0.070 (2) | 0.0001 (16) | 0.0033 (16) | 0.0184 (19) |
C12 | 0.062 (2) | 0.114 (3) | 0.076 (3) | −0.009 (2) | −0.010 (2) | 0.018 (2) |
C13 | 0.087 (3) | 0.123 (4) | 0.059 (2) | −0.011 (3) | −0.013 (2) | 0.001 (2) |
C14 | 0.080 (3) | 0.093 (3) | 0.053 (2) | −0.003 (2) | 0.0040 (18) | −0.0002 (19) |
C17 | 0.055 (2) | 0.101 (3) | 0.090 (3) | 0.006 (2) | 0.010 (2) | 0.013 (3) |
N1 | 0.0534 (16) | 0.079 (2) | 0.0473 (15) | 0.0098 (14) | 0.0092 (12) | −0.0084 (14) |
O1 | 0.0895 (19) | 0.0852 (18) | 0.0517 (13) | −0.0070 (14) | 0.0193 (12) | 0.0124 (13) |
O2 | 0.0517 (12) | 0.0736 (15) | 0.0478 (11) | −0.0076 (10) | 0.0153 (9) | −0.0016 (11) |
F1 | 0.0621 (16) | 0.253 (5) | 0.158 (3) | 0.044 (2) | 0.0021 (17) | −0.030 (3) |
F2 | 0.210 (4) | 0.168 (3) | 0.176 (3) | 0.061 (3) | 0.134 (3) | 0.073 (3) |
F3 | 0.0864 (19) | 0.157 (3) | 0.143 (3) | −0.0073 (19) | 0.0431 (18) | −0.043 (2) |
Geometric parameters (Å, º) top
C1—O1 | 1.203 (4) | C9—C10 | 1.384 (5) |
C1—O2 | 1.344 (4) | C9—C14 | 1.390 (5) |
C1—C2 | 1.463 (4) | C9—N1 | 1.393 (4) |
C2—C3 | 1.372 (5) | C10—C11 | 1.388 (5) |
C2—C7 | 1.378 (4) | C10—H10 | 0.9300 |
C3—C4 | 1.370 (5) | C11—C12 | 1.376 (6) |
C3—H3 | 0.9300 | C11—C17 | 1.471 (6) |
C4—C5 | 1.387 (6) | C12—C13 | 1.376 (6) |
C4—H4 | 0.9300 | C12—H12 | 0.9300 |
C5—C6 | 1.378 (5) | C13—C14 | 1.379 (6) |
C5—H5 | 0.9300 | C13—H13 | 0.9300 |
C6—C7 | 1.387 (4) | C14—H14 | 0.9300 |
C6—H6 | 0.9300 | C17—F1 | 1.295 (5) |
C7—C8 | 1.500 (4) | C17—F2 | 1.309 (5) |
C8—N1 | 1.392 (4) | C17—F3 | 1.337 (6) |
C8—O2 | 1.497 (4) | N1—H1 | 0.83 (4) |
C8—H8 | 0.9800 | | |
| | | |
O1—C1—O2 | 122.0 (3) | C10—C9—N1 | 122.2 (3) |
O1—C1—C2 | 128.8 (3) | C14—C9—N1 | 118.7 (3) |
O2—C1—C2 | 109.2 (3) | C9—C10—C11 | 119.9 (3) |
C3—C2—C7 | 122.1 (3) | C9—C10—H10 | 120.0 |
C3—C2—C1 | 129.9 (3) | C11—C10—H10 | 120.0 |
C7—C2—C1 | 108.1 (3) | C12—C11—C10 | 120.9 (4) |
C4—C3—C2 | 117.9 (4) | C12—C11—C17 | 119.1 (4) |
C4—C3—H3 | 121.1 | C10—C11—C17 | 120.0 (4) |
C2—C3—H3 | 121.1 | C13—C12—C11 | 118.8 (4) |
C3—C4—C5 | 120.4 (3) | C13—C12—H12 | 120.6 |
C3—C4—H4 | 119.8 | C11—C12—H12 | 120.6 |
C5—C4—H4 | 119.8 | C12—C13—C14 | 121.1 (4) |
C6—C5—C4 | 122.0 (3) | C12—C13—H13 | 119.4 |
C6—C5—H5 | 119.0 | C14—C13—H13 | 119.4 |
C4—C5—H5 | 119.0 | C13—C14—C9 | 120.0 (4) |
C5—C6—C7 | 117.0 (3) | C13—C14—H14 | 120.0 |
C5—C6—H6 | 121.5 | C9—C14—H14 | 120.0 |
C7—C6—H6 | 121.5 | F1—C17—F2 | 105.4 (4) |
C2—C7—C6 | 120.6 (3) | F1—C17—F3 | 104.2 (4) |
C2—C7—C8 | 109.7 (3) | F2—C17—F3 | 102.2 (4) |
C6—C7—C8 | 129.8 (3) | F1—C17—C11 | 115.9 (4) |
N1—C8—O2 | 111.5 (3) | F2—C17—C11 | 113.7 (4) |
N1—C8—C7 | 114.1 (2) | F3—C17—C11 | 114.1 (4) |
O2—C8—C7 | 102.3 (2) | C8—N1—C9 | 124.1 (3) |
N1—C8—H8 | 109.6 | C8—N1—H1 | 122 (3) |
O2—C8—H8 | 109.6 | C9—N1—H1 | 113 (3) |
C7—C8—H8 | 109.6 | C1—O2—C8 | 110.6 (2) |
C10—C9—C14 | 119.1 (3) | | |
| | | |
O1—C1—C2—C3 | −0.4 (6) | C9—C10—C11—C17 | −179.1 (4) |
O2—C1—C2—C3 | 179.6 (3) | C10—C11—C12—C13 | −0.2 (6) |
O1—C1—C2—C7 | −179.4 (3) | C17—C11—C12—C13 | 178.6 (4) |
O2—C1—C2—C7 | 0.5 (3) | C11—C12—C13—C14 | 0.9 (7) |
C7—C2—C3—C4 | −0.3 (5) | C12—C13—C14—C9 | −1.2 (7) |
C1—C2—C3—C4 | −179.2 (3) | C10—C9—C14—C13 | 0.8 (6) |
C2—C3—C4—C5 | 1.1 (6) | N1—C9—C14—C13 | −179.3 (4) |
C3—C4—C5—C6 | −0.7 (7) | C12—C11—C17—F1 | 17.7 (6) |
C4—C5—C6—C7 | −0.6 (6) | C10—C11—C17—F1 | −163.5 (4) |
C3—C2—C7—C6 | −1.1 (5) | C12—C11—C17—F2 | −104.6 (5) |
C1—C2—C7—C6 | 178.1 (3) | C10—C11—C17—F2 | 74.2 (6) |
C3—C2—C7—C8 | 178.1 (3) | C12—C11—C17—F3 | 138.8 (4) |
C1—C2—C7—C8 | −2.8 (3) | C10—C11—C17—F3 | −42.5 (5) |
C5—C6—C7—C2 | 1.5 (5) | O2—C8—N1—C9 | −67.3 (4) |
C5—C6—C7—C8 | −177.5 (3) | C7—C8—N1—C9 | 177.4 (3) |
C2—C7—C8—N1 | 124.2 (3) | C10—C9—N1—C8 | 1.7 (5) |
C6—C7—C8—N1 | −56.7 (5) | C14—C9—N1—C8 | −178.2 (3) |
C2—C7—C8—O2 | 3.7 (3) | O1—C1—O2—C8 | −178.2 (3) |
C6—C7—C8—O2 | −177.2 (3) | C2—C1—O2—C8 | 1.9 (3) |
C14—C9—C10—C11 | 0.0 (5) | N1—C8—O2—C1 | −125.7 (3) |
N1—C9—C10—C11 | −179.9 (3) | C7—C8—O2—C1 | −3.4 (3) |
C9—C10—C11—C12 | −0.3 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.83 (4) | 2.14 (4) | 2.962 (4) | 176 (4) |
C8—H8···O1ii | 0.98 | 2.52 | 3.264 (4) | 133 |
C8—H8···Cg1iii | 0.98 | 3.31 | 3.979 (4) | 128 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+1/2. |