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organic compounds
4-[3-(Trifluoromethyl)phenyl]-5,6,7,8-tetrahydrocinnolin-3(2H)-one
aState Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China
*Correspondence e-mail: wanggengmin@tju.edu.cn, nk_yanghz@126.com
The title compound, C15H13F3N2O, contains one benzene ring, one cyclohexane ring and a pyridazine ring. The dihedral angle formed by the pyridazine ring with the benzene ring is 61.5 (2)°. The is stabilized by two intermolecular hydrogen bonds (N—H⋯O and C—H⋯F). The cyclohexane ring adopts a screw-boat conformation. The CF3 group is disordered over two positions; the site occupancy factors are ca 0.6 and 0.4.
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1999); cell SAINT (Bruker, 1999
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: SHELXTL (Sheldrick, 2008
); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808000871/at2529sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808000871/at2529Isup2.hkl
4-(3-(Trifluoromethyl)phenyl)-4,4a,5,6,7,8-hexahydrocinnolin-3(2H)-one (1.5 mmol), and 0.5 g anhydrous copper(II) chloride were mixed in acetonitrile (40 ml), refluxed for 2 h. Water (20 ml) were then added. The organic layer was washed successively with saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfateThe solvent was then evaporated in vacuo. The residue was purified via
single crystals of (I) suitable for X-ray analysis were grown from ethyl acetate and petroleum ether at room temperature.The trifluoromethyl group shows positional disorder. At the final stage of the
the occupancy factors of two possible sites, C15/F1/F2/F3 and C15/F1'/F2'/F3', were fixed at 0.429 and 0.571 respectively. All H atoms were positioned geometrically, with C—H = 0.93 and 0.97 A° and N—H = 0.91 (4) A°, and included in the final cycles of using a riding model, with Uiso(H) = 1.2Ueq(C).Data collection: SMART (Bruker, 1999); cell
SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C15H13F3N2O | F(000) = 1216 |
Mr = 294.27 | Dx = 1.398 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1012 reflections |
a = 8.929 (3) Å | θ = 2.9–20.2° |
b = 11.443 (4) Å | µ = 0.12 mm−1 |
c = 27.448 (8) Å | T = 294 K |
β = 94.232 (6)° | Prism, colourless |
V = 2796.6 (15) Å3 | 0.22 × 0.20 × 0.16 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 2485 independent reflections |
Radiation source: fine-focus sealed tube | 1098 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.975, Tmax = 0.982 | k = −13→8 |
7053 measured reflections | l = −32→32 |
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)] = 0.068 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.212 | w = 1/[σ2(Fo2) + (0.0738P)2 + 4.8514P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
2485 reflections | Δρmax = 0.32 e Å−3 |
223 parameters | Δρmin = −0.27 e Å−3 |
85 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0029 (8) |
C15H13F3N2O | V = 2796.6 (15) Å3 |
Mr = 294.27 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 8.929 (3) Å | µ = 0.12 mm−1 |
b = 11.443 (4) Å | T = 294 K |
c = 27.448 (8) Å | 0.22 × 0.20 × 0.16 mm |
β = 94.232 (6)° |
Bruker SMART CCD area-detector diffractometer | 2485 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1098 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.982 | Rint = 0.061 |
7053 measured reflections |
R[F2 > 2σ(F2)] = 0.068 | 85 restraints |
wR(F2) = 0.212 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.32 e Å−3 |
2485 reflections | Δρmin = −0.27 e Å−3 |
223 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
F1 | 1.1701 (18) | 0.1095 (16) | 0.2649 (5) | 0.144 (5) | 0.429 (9) |
F2 | 1.3627 (15) | 0.1988 (12) | 0.2422 (6) | 0.167 (5) | 0.429 (9) |
F3 | 1.274 (2) | 0.0347 (12) | 0.2066 (5) | 0.139 (5) | 0.429 (9) |
F1' | 1.2515 (15) | 0.1731 (11) | 0.2699 (3) | 0.152 (4) | 0.571 (9) |
F2' | 1.3577 (10) | 0.0982 (12) | 0.2113 (4) | 0.130 (4) | 0.571 (9) |
F3' | 1.1498 (13) | 0.0330 (10) | 0.2327 (5) | 0.170 (4) | 0.571 (9) |
O1 | 1.0587 (4) | 0.0810 (3) | 0.05160 (12) | 0.0661 (10) | |
N1 | 0.6764 (5) | 0.0930 (3) | 0.00974 (15) | 0.0601 (11) | |
N2 | 0.8244 (5) | 0.0709 (4) | 0.01511 (15) | 0.0579 (11) | |
C1 | 0.6214 (5) | 0.1615 (4) | 0.04183 (19) | 0.0547 (13) | |
C2 | 0.4543 (5) | 0.1771 (5) | 0.0370 (2) | 0.0755 (16) | |
H2A | 0.4236 | 0.1960 | 0.0033 | 0.091* | |
H2B | 0.4074 | 0.1035 | 0.0446 | 0.091* | |
C3 | 0.3977 (7) | 0.2691 (7) | 0.0689 (3) | 0.120 (3) | |
H3A | 0.4001 | 0.3431 | 0.0518 | 0.144* | |
H3B | 0.2935 | 0.2522 | 0.0739 | 0.144* | |
C4 | 0.4780 (7) | 0.2826 (7) | 0.1160 (3) | 0.103 (2) | |
H4A | 0.4599 | 0.2141 | 0.1356 | 0.124* | |
H4B | 0.4373 | 0.3496 | 0.1322 | 0.124* | |
C5 | 0.6424 (6) | 0.2986 (5) | 0.11490 (19) | 0.0708 (16) | |
H5A | 0.6891 | 0.2872 | 0.1476 | 0.085* | |
H5B | 0.6622 | 0.3784 | 0.1053 | 0.085* | |
C6 | 0.7142 (5) | 0.2159 (4) | 0.08030 (17) | 0.0533 (13) | |
C7 | 0.8642 (5) | 0.1920 (4) | 0.08449 (15) | 0.0480 (12) | |
C8 | 0.9248 (6) | 0.1122 (4) | 0.05062 (16) | 0.0497 (12) | |
C9 | 0.9705 (5) | 0.2428 (4) | 0.12244 (17) | 0.0539 (13) | |
C10 | 0.9951 (6) | 0.3607 (5) | 0.1261 (2) | 0.0813 (18) | |
H10 | 0.9450 | 0.4107 | 0.1036 | 0.098* | |
C11 | 1.0930 (7) | 0.4069 (6) | 0.1624 (3) | 0.111 (3) | |
H11 | 1.1075 | 0.4872 | 0.1647 | 0.133* | |
C12 | 1.1682 (7) | 0.3337 (8) | 0.1950 (3) | 0.110 (3) | |
H12 | 1.2339 | 0.3643 | 0.2196 | 0.133* | |
C13 | 1.1474 (6) | 0.2162 (7) | 0.1915 (2) | 0.083 (2) | |
C14 | 1.0497 (5) | 0.1703 (5) | 0.15529 (17) | 0.0650 (15) | |
H14 | 1.0369 | 0.0898 | 0.1530 | 0.078* | |
C15 | 1.2323 (9) | 0.1368 (8) | 0.2247 (2) | 0.114 (3) | |
H2 | 0.862 (5) | 0.023 (4) | −0.0072 (14) | 0.081 (18)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.165 (9) | 0.167 (9) | 0.102 (7) | 0.031 (7) | 0.032 (7) | 0.026 (7) |
F2 | 0.139 (8) | 0.198 (9) | 0.157 (8) | 0.018 (7) | −0.044 (7) | 0.025 (7) |
F3 | 0.150 (9) | 0.146 (8) | 0.118 (7) | 0.075 (7) | −0.004 (7) | 0.012 (6) |
F1' | 0.179 (8) | 0.207 (8) | 0.064 (4) | −0.003 (7) | −0.021 (5) | 0.006 (5) |
F2' | 0.102 (5) | 0.166 (8) | 0.123 (6) | 0.071 (5) | 0.011 (5) | 0.020 (6) |
F3' | 0.158 (7) | 0.185 (7) | 0.157 (7) | 0.032 (6) | −0.052 (6) | 0.061 (6) |
O1 | 0.057 (2) | 0.068 (2) | 0.071 (2) | 0.0144 (17) | −0.0021 (17) | −0.0177 (19) |
N1 | 0.059 (3) | 0.052 (3) | 0.068 (3) | 0.002 (2) | −0.004 (2) | −0.001 (2) |
N2 | 0.058 (3) | 0.053 (3) | 0.061 (3) | 0.007 (2) | −0.005 (2) | −0.010 (2) |
C1 | 0.053 (3) | 0.045 (3) | 0.065 (3) | 0.000 (2) | −0.004 (3) | 0.004 (3) |
C2 | 0.054 (3) | 0.071 (4) | 0.099 (4) | 0.002 (3) | −0.004 (3) | 0.003 (4) |
C3 | 0.059 (4) | 0.150 (7) | 0.147 (7) | 0.020 (4) | −0.005 (4) | −0.044 (6) |
C4 | 0.068 (4) | 0.135 (6) | 0.109 (5) | 0.009 (4) | 0.021 (4) | −0.014 (5) |
C5 | 0.065 (3) | 0.078 (4) | 0.070 (3) | 0.018 (3) | 0.002 (3) | −0.009 (3) |
C6 | 0.059 (3) | 0.046 (3) | 0.055 (3) | 0.006 (2) | 0.004 (2) | 0.007 (2) |
C7 | 0.056 (3) | 0.041 (3) | 0.047 (3) | 0.006 (2) | 0.001 (2) | 0.002 (2) |
C8 | 0.055 (3) | 0.042 (3) | 0.051 (3) | 0.005 (2) | 0.000 (3) | −0.002 (2) |
C9 | 0.056 (3) | 0.056 (3) | 0.049 (3) | 0.013 (2) | 0.000 (2) | −0.009 (3) |
C10 | 0.076 (4) | 0.062 (4) | 0.102 (5) | 0.008 (3) | −0.020 (3) | −0.019 (3) |
C11 | 0.091 (5) | 0.085 (5) | 0.152 (7) | 0.013 (4) | −0.026 (5) | −0.055 (5) |
C12 | 0.074 (4) | 0.150 (7) | 0.104 (5) | 0.032 (5) | −0.020 (4) | −0.063 (6) |
C13 | 0.064 (4) | 0.131 (6) | 0.051 (3) | 0.039 (4) | −0.009 (3) | −0.017 (4) |
C14 | 0.069 (3) | 0.076 (4) | 0.049 (3) | 0.021 (3) | 0.002 (3) | −0.002 (3) |
C15 | 0.102 (6) | 0.155 (7) | 0.080 (5) | 0.016 (5) | −0.025 (4) | −0.003 (5) |
F1—C15 | 1.310 (9) | C4—H4A | 0.9700 |
F2—C15 | 1.416 (9) | C4—H4B | 0.9700 |
F3—C15 | 1.333 (9) | C5—C6 | 1.516 (7) |
F1'—C15 | 1.308 (8) | C5—H5A | 0.9700 |
F2'—C15 | 1.282 (8) | C5—H5B | 0.9700 |
F3'—C15 | 1.423 (9) | C6—C7 | 1.363 (6) |
O1—C8 | 1.246 (5) | C7—C8 | 1.437 (6) |
N1—C1 | 1.302 (6) | C7—C9 | 1.476 (6) |
N1—N2 | 1.343 (5) | C9—C10 | 1.370 (7) |
N2—C8 | 1.360 (6) | C9—C14 | 1.381 (6) |
N2—H2 | 0.91 (4) | C10—C11 | 1.382 (8) |
C1—C6 | 1.435 (6) | C10—H10 | 0.9300 |
C1—C2 | 1.499 (6) | C11—C12 | 1.364 (9) |
C2—C3 | 1.481 (8) | C11—H11 | 0.9300 |
C2—H2A | 0.9700 | C12—C13 | 1.360 (9) |
C2—H2B | 0.9700 | C12—H12 | 0.9300 |
C3—C4 | 1.441 (8) | C13—C14 | 1.377 (7) |
C3—H3A | 0.9700 | C13—C15 | 1.459 (9) |
C3—H3B | 0.9700 | C14—H14 | 0.9300 |
C4—C5 | 1.482 (7) | ||
C1—N1—N2 | 117.2 (4) | C10—C9—C14 | 118.2 (5) |
N1—N2—C8 | 127.2 (4) | C10—C9—C7 | 122.0 (5) |
N1—N2—H2 | 117 (3) | C14—C9—C7 | 119.7 (5) |
C8—N2—H2 | 116 (3) | C9—C10—C11 | 121.2 (6) |
N1—C1—C6 | 122.2 (4) | C9—C10—H10 | 119.4 |
N1—C1—C2 | 115.8 (5) | C11—C10—H10 | 119.4 |
C6—C1—C2 | 122.0 (5) | C12—C11—C10 | 119.5 (7) |
C3—C2—C1 | 114.4 (5) | C12—C11—H11 | 120.2 |
C3—C2—H2A | 108.7 | C10—C11—H11 | 120.2 |
C1—C2—H2A | 108.7 | C13—C12—C11 | 120.2 (6) |
C3—C2—H2B | 108.7 | C13—C12—H12 | 119.9 |
C1—C2—H2B | 108.7 | C11—C12—H12 | 119.9 |
H2A—C2—H2B | 107.6 | C12—C13—C14 | 120.2 (6) |
C4—C3—C2 | 115.9 (6) | C12—C13—C15 | 120.6 (7) |
C4—C3—H3A | 108.3 | C14—C13—C15 | 119.1 (7) |
C2—C3—H3A | 108.3 | C13—C14—C9 | 120.6 (6) |
C4—C3—H3B | 108.3 | C13—C14—H14 | 119.7 |
C2—C3—H3B | 108.3 | C9—C14—H14 | 119.7 |
H3A—C3—H3B | 107.4 | F2'—C15—F1' | 109.0 (9) |
C3—C4—C5 | 115.0 (6) | F2'—C15—F1 | 126.4 (9) |
C3—C4—H4A | 108.5 | F1'—C15—F1 | 46.3 (8) |
C5—C4—H4A | 108.5 | F2'—C15—F3 | 47.0 (8) |
C3—C4—H4B | 108.5 | F1'—C15—F3 | 127.7 (10) |
C5—C4—H4B | 108.5 | F1—C15—F3 | 104.7 (12) |
H4A—C4—H4B | 107.5 | F2'—C15—F2 | 63.7 (8) |
C4—C5—C6 | 113.7 (5) | F1'—C15—F2 | 58.2 (8) |
C4—C5—H5A | 108.8 | F1—C15—F2 | 102.9 (11) |
C6—C5—H5A | 108.8 | F3—C15—F2 | 108.7 (12) |
C4—C5—H5B | 108.8 | F2'—C15—F3' | 103.3 (10) |
C6—C5—H5B | 108.8 | F1'—C15—F3' | 98.7 (10) |
H5A—C5—H5B | 107.7 | F1—C15—F3' | 54.2 (8) |
C7—C6—C1 | 119.0 (4) | F3—C15—F3' | 59.2 (9) |
C7—C6—C5 | 122.0 (4) | F2—C15—F3' | 142.0 (8) |
C1—C6—C5 | 118.9 (4) | F2'—C15—C13 | 117.3 (7) |
C6—C7—C8 | 119.2 (4) | F1'—C15—C13 | 114.9 (8) |
C6—C7—C9 | 123.9 (4) | F1—C15—C13 | 116.2 (9) |
C8—C7—C9 | 116.9 (4) | F3—C15—C13 | 117.3 (8) |
O1—C8—N2 | 119.7 (4) | F2—C15—C13 | 106.0 (8) |
O1—C8—C7 | 125.1 (4) | F3'—C15—C13 | 111.4 (7) |
N2—C8—C7 | 115.2 (4) | ||
C1—N1—N2—C8 | 0.0 (7) | C8—C7—C9—C10 | 119.0 (5) |
N2—N1—C1—C6 | 2.7 (6) | C6—C7—C9—C14 | 119.2 (5) |
N2—N1—C1—C2 | −175.5 (4) | C8—C7—C9—C14 | −60.3 (6) |
N1—C1—C2—C3 | −170.9 (5) | C14—C9—C10—C11 | −1.9 (9) |
C6—C1—C2—C3 | 10.9 (8) | C7—C9—C10—C11 | 178.7 (5) |
C1—C2—C3—C4 | −34.6 (9) | C9—C10—C11—C12 | 0.9 (10) |
C2—C3—C4—C5 | 52.9 (10) | C10—C11—C12—C13 | 0.3 (11) |
C3—C4—C5—C6 | −44.3 (8) | C11—C12—C13—C14 | −0.4 (10) |
N1—C1—C6—C7 | −2.3 (7) | C11—C12—C13—C15 | 177.2 (7) |
C2—C1—C6—C7 | 175.7 (4) | C12—C13—C14—C9 | −0.6 (8) |
N1—C1—C6—C5 | 177.4 (4) | C15—C13—C14—C9 | −178.3 (5) |
C2—C1—C6—C5 | −4.5 (7) | C10—C9—C14—C13 | 1.8 (8) |
C4—C5—C6—C7 | −159.9 (5) | C7—C9—C14—C13 | −178.9 (5) |
C4—C5—C6—C1 | 20.4 (7) | C12—C13—C15—F2' | −90.7 (11) |
C1—C6—C7—C8 | −0.6 (6) | C14—C13—C15—F2' | 86.9 (12) |
C5—C6—C7—C8 | 179.6 (4) | C12—C13—C15—F1' | 39.4 (13) |
C1—C6—C7—C9 | 179.9 (4) | C14—C13—C15—F1' | −142.9 (10) |
C5—C6—C7—C9 | 0.2 (7) | C12—C13—C15—F1 | 91.1 (14) |
N1—N2—C8—O1 | 177.9 (4) | C14—C13—C15—F1 | −91.3 (14) |
N1—N2—C8—C7 | −2.7 (7) | C12—C13—C15—F3 | −144.0 (13) |
C6—C7—C8—O1 | −177.8 (4) | C14—C13—C15—F3 | 33.7 (15) |
C9—C7—C8—O1 | 1.7 (7) | C12—C13—C15—F2 | −22.5 (12) |
C6—C7—C8—N2 | 2.9 (6) | C14—C13—C15—F2 | 155.2 (10) |
C9—C7—C8—N2 | −177.6 (4) | C12—C13—C15—F3' | 150.6 (10) |
C6—C7—C9—C10 | −61.5 (7) | C14—C13—C15—F3' | −31.8 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 0.91 (4) | 1.88 (4) | 2.783 (5) | 178 (5) |
C12—H12···F3′ii | 0.93 | 2.51 | 3.362 | 152 |
Symmetry codes: (i) −x+2, −y, −z; (ii) −x+5/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H13F3N2O |
Mr | 294.27 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 294 |
a, b, c (Å) | 8.929 (3), 11.443 (4), 27.448 (8) |
β (°) | 94.232 (6) |
V (Å3) | 2796.6 (15) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.22 × 0.20 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.975, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7053, 2485, 1098 |
Rint | 0.061 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.212, 1.02 |
No. of reflections | 2485 |
No. of parameters | 223 |
No. of restraints | 85 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.32, −0.27 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 0.91 (4) | 1.88 (4) | 2.783 (5) | 178 (5) |
C12—H12···F3'ii | 0.93 | 2.51 | 3.362 | 152 |
Symmetry codes: (i) −x+2, −y, −z; (ii) −x+5/2, y+1/2, −z+1/2. |
Acknowledgements
This work was supported by the National Key Project for Basic Research (grant No. 20772067).
References
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Many pyridazine derivatives have been found to exhibit biological activities such as insecticidal, fungicidal, herbicidal, plant-growth regulatory activity, etc. (Heinisch & Kopelent, 1992). For example, pyridate, credazine and maleic hydrazide (Kolar & Tisler, 1999) have been commercialized as herbicides. In order to discover new biologically active pyridazine compounds, the title compound, (I), was synthesized and its structure is reported here.
In the molecule of (I) (Fig. 1), the central pyridazine ring (C1—C8/N1/N2) is approximately coplanar with the cyclohexane ring (C1—C6) [dihedral angle = 4.36 (29)°] and the largest deviation from the mean plane is 0.306 (6) Å for atom C4. The dihedral angle formed by the heterocycle and the benzene ring (C9—C14) is 61.50 (18)°. The molecule is further stabilized by intermolecular N—H···O and C—H···F hydrogen bonds(Table 1). Glide-related molecules are linked via C—H···F hydrogen-bonded chains along the c axis. Part of the chain structure is shown in Fig. 2.