(Z)-1-[4-Fluoro-2-(pyrrolidin-1-yl)phen-yl]-3-phenyl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one.

In the title mol-ecule, C(21)H(19)FN(4)O, the triazole ring forms dihedral angles of 67.0 (1) and 59.6 (1)° with the phenyl and fluoro-substituted benzene rings, respectively. The dihedral angle between the phenyl ring and the fluoro-substituted benzene ring is 79.1 (1)°. The pyrrolidine ring is in a half-chair conformation. In the crystal, weak C-H⋯O and C-H⋯N hydrogen bonds connect mol-ecules into layers parallel to (001).

Related literature

For clinical uses of triazole compounds, see: Wang & Zhou (2011 ▶); Zhou & Wang (2012 ▶); Chang et al. (2011 ▶). For the synthesis, see: Solankee et al. (2010 ▶). For related structures, see: Wang et al. (2009 ▶); Yan et al. (2009 ▶).

Experimental

Crystal data

C21H19FN4O

M = 362.40

Monoclinic,

a = 11.217 (2) Å

b = 10.067 (2) Å

c = 15.793 (3) Å

β = 94.47 (3)°

V = 1778.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.30 × 0.08 × 0.03 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996) ▶ T min = 0.973, T max = 0.997

13447 measured reflections

3403 independent reflections

2341 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.118

S = 1.05

3403 reflections

321 parameters

2 restraints

All H-atom parameters refined

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018454/lh5432sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018454/lh5432Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018454/lh5432Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H19FN4O	Z = 4
Mr = 362.40	F(000) = 760
Monoclinic, P21/c	Dx = 1.354 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.217 (2) Å	θ = 2.3–27.7°
b = 10.067 (2) Å	µ = 0.09 mm−1
c = 15.793 (3) Å	T = 173 K
β = 94.47 (3)°	Plate, yellow
V = 1778.0 (6) Å3	0.30 × 0.08 × 0.03 mm

Bruker SMART CCD diffractometer	3403 independent reflections
Radiation source: fine-focus sealed tube	2341 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
φ and ω scans	θmax = 26.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.973, Tmax = 0.997	k = −11→12
13447 measured reflections	l = −19→19

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)] = 0.048	All H-atom parameters refined
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0576P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3403 reflections	Δρmax = 0.23 e Å−3
321 parameters	Δρmin = −0.19 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0075 (13)

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
F1	0.06331 (9)	0.07121 (12)	0.14879 (7)	0.0506 (4)
N3	0.73647 (12)	−0.01216 (15)	0.27605 (9)	0.0291 (4)
O1	0.54633 (11)	0.01888 (14)	0.36550 (8)	0.0389 (4)
C8	0.62355 (15)	−0.06156 (19)	0.24237 (11)	0.0289 (4)
C16	0.18387 (18)	−0.0239 (2)	0.25987 (13)	0.0340 (5)
C17	0.29747 (16)	−0.06191 (18)	0.29689 (11)	0.0290 (4)
C12	0.39893 (16)	−0.02771 (18)	0.25277 (11)	0.0290 (4)
N2	0.76525 (14)	0.11901 (16)	0.27051 (10)	0.0378 (4)
N4	0.30375 (13)	−0.13062 (16)	0.37147 (9)	0.0320 (4)
C13	0.38080 (18)	0.02722 (19)	0.17088 (12)	0.0336 (5)
C6	0.70879 (16)	−0.19160 (19)	0.12221 (11)	0.0291 (4)
C11	0.52247 (16)	−0.02255 (19)	0.29265 (12)	0.0306 (5)
C7	0.61641 (17)	−0.14582 (19)	0.17621 (11)	0.0312 (5)
C3	0.87605 (18)	−0.2952 (2)	0.01763 (12)	0.0369 (5)
N1	0.91459 (14)	0.00330 (19)	0.34166 (10)	0.0422 (5)
C5	0.68283 (18)	−0.3030 (2)	0.07170 (11)	0.0324 (5)
C2	0.90214 (18)	−0.1816 (2)	0.06478 (12)	0.0369 (5)
C1	0.82010 (17)	−0.1292 (2)	0.11679 (12)	0.0330 (5)
C15	0.17490 (16)	0.0344 (2)	0.18190 (13)	0.0363 (5)
C18	0.19584 (18)	−0.1755 (2)	0.41003 (13)	0.0387 (5)
C10	0.82587 (17)	−0.0775 (2)	0.31872 (12)	0.0354 (5)
C9	0.87283 (19)	0.1214 (2)	0.31018 (13)	0.0406 (5)
C14	0.26982 (18)	0.0594 (2)	0.13393 (14)	0.0365 (5)
C4	0.76540 (19)	−0.3541 (2)	0.01975 (12)	0.0365 (5)
C21	0.40905 (18)	−0.2063 (2)	0.40537 (14)	0.0392 (5)
C20	0.3575 (2)	−0.3164 (2)	0.45719 (15)	0.0446 (6)
C19	0.2455 (2)	−0.2535 (3)	0.48764 (15)	0.0477 (6)
H15	0.5351 (16)	−0.1852 (18)	0.1620 (10)	0.031 (5)*
H23	0.1166 (17)	−0.0388 (19)	0.2867 (12)	0.038 (6)*
H3A	0.4540 (15)	−0.2398 (18)	0.3554 (11)	0.037 (5)*
H5	0.2578 (17)	0.1005 (19)	0.0796 (12)	0.042 (6)*
H12	0.6041 (17)	−0.3451 (19)	0.0728 (11)	0.036 (5)*
H7	0.8209 (17)	−0.174 (2)	0.3276 (12)	0.044 (6)*
H8A	0.1441 (17)	−0.096 (2)	0.4266 (11)	0.043 (6)*
H2A	0.3393 (17)	−0.396 (2)	0.4217 (12)	0.044 (6)*
H18	0.4500 (16)	0.0451 (18)	0.1429 (12)	0.037 (5)*
H6	0.9173 (18)	0.205 (2)	0.3160 (12)	0.048 (6)*
H4	0.7450 (17)	−0.432 (2)	−0.0150 (12)	0.041 (6)*
H14	0.9352 (18)	−0.332 (2)	−0.0180 (11)	0.047 (6)*
H11	0.9777 (18)	−0.1339 (19)	0.0632 (11)	0.039 (5)*
H8B	0.1457 (18)	−0.2321 (19)	0.3678 (12)	0.046 (6)*
H10	0.8385 (17)	−0.0451 (19)	0.1478 (12)	0.044 (6)*
H3B	0.4656 (19)	−0.144 (2)	0.4417 (13)	0.057 (7)*
H1A	0.1847 (19)	−0.322 (2)	0.5052 (13)	0.060 (7)*
H2B	0.4184 (19)	−0.346 (2)	0.5040 (12)	0.049 (6)*
H1B	0.267 (2)	−0.193 (2)	0.5352 (14)	0.068 (8)*

	U11	U22	U33	U12	U13	U23
F1	0.0285 (7)	0.0611 (9)	0.0608 (8)	0.0060 (6)	−0.0043 (6)	0.0095 (6)
N3	0.0224 (8)	0.0345 (10)	0.0308 (8)	−0.0006 (7)	0.0053 (7)	−0.0009 (7)
O1	0.0283 (8)	0.0522 (10)	0.0372 (8)	−0.0007 (7)	0.0075 (6)	−0.0078 (7)
C8	0.0218 (10)	0.0320 (11)	0.0329 (10)	0.0000 (8)	0.0030 (8)	0.0016 (9)
C16	0.0223 (10)	0.0366 (12)	0.0439 (12)	−0.0043 (9)	0.0078 (9)	−0.0025 (10)
C17	0.0254 (10)	0.0299 (11)	0.0322 (10)	−0.0002 (8)	0.0048 (8)	−0.0047 (8)
C12	0.0236 (10)	0.0302 (11)	0.0337 (10)	0.0025 (8)	0.0058 (8)	−0.0019 (8)
N2	0.0318 (10)	0.0360 (10)	0.0458 (10)	−0.0048 (8)	0.0035 (8)	−0.0013 (8)
N4	0.0231 (8)	0.0370 (10)	0.0367 (9)	0.0018 (7)	0.0083 (7)	−0.0001 (7)
C13	0.0277 (11)	0.0356 (12)	0.0387 (11)	−0.0006 (9)	0.0098 (10)	0.0000 (9)
C6	0.0257 (10)	0.0330 (11)	0.0288 (10)	0.0029 (9)	0.0035 (8)	0.0026 (8)
C11	0.0268 (10)	0.0327 (11)	0.0329 (11)	0.0002 (9)	0.0066 (9)	0.0015 (9)
C7	0.0235 (10)	0.0355 (12)	0.0355 (11)	−0.0020 (9)	0.0070 (9)	0.0044 (9)
C3	0.0363 (12)	0.0447 (13)	0.0306 (10)	0.0121 (10)	0.0084 (9)	0.0003 (10)
N1	0.0268 (9)	0.0613 (13)	0.0389 (10)	−0.0053 (9)	0.0053 (8)	0.0048 (9)
C5	0.0337 (11)	0.0331 (12)	0.0308 (10)	−0.0020 (10)	0.0042 (9)	0.0042 (9)
C2	0.0249 (11)	0.0521 (14)	0.0341 (11)	0.0002 (10)	0.0048 (9)	0.0006 (10)
C1	0.0272 (11)	0.0398 (12)	0.0325 (10)	0.0008 (9)	0.0060 (9)	−0.0008 (10)
C15	0.0219 (10)	0.0383 (12)	0.0480 (12)	0.0018 (9)	−0.0028 (9)	−0.0021 (10)
C18	0.0315 (11)	0.0439 (14)	0.0429 (12)	−0.0019 (10)	0.0172 (10)	0.0001 (10)
C10	0.0260 (11)	0.0468 (14)	0.0340 (11)	0.0029 (10)	0.0068 (9)	0.0041 (10)
C9	0.0330 (12)	0.0464 (14)	0.0427 (12)	−0.0101 (11)	0.0049 (10)	−0.0016 (11)
C14	0.0358 (12)	0.0367 (12)	0.0371 (12)	0.0028 (10)	0.0032 (10)	0.0045 (10)
C4	0.0436 (13)	0.0345 (13)	0.0319 (11)	0.0027 (10)	0.0069 (10)	−0.0014 (10)
C21	0.0328 (12)	0.0448 (14)	0.0409 (12)	0.0070 (11)	0.0086 (10)	0.0048 (11)
C20	0.0460 (14)	0.0441 (15)	0.0447 (13)	0.0036 (12)	0.0099 (11)	0.0071 (12)
C19	0.0506 (15)	0.0478 (15)	0.0471 (13)	−0.0030 (12)	0.0187 (12)	0.0058 (12)

F1—C15	1.370 (2)	C3—H14	0.974 (19)
N3—C10	1.337 (2)	N1—C10	1.314 (3)
N3—N2	1.364 (2)	N1—C9	1.358 (3)
N3—C8	1.425 (2)	C5—C4	1.383 (3)
O1—C11	1.233 (2)	C5—H12	0.980 (19)
C8—C7	1.343 (3)	C2—C1	1.385 (3)
C8—C11	1.487 (2)	C2—H11	0.976 (19)
C16—C15	1.361 (3)	C1—H10	0.99 (2)
C16—C17	1.413 (3)	C15—C14	1.377 (3)
C16—H23	0.906 (19)	C18—C19	1.524 (3)
C17—N4	1.363 (2)	C18—H8A	1.03 (2)
C17—C12	1.422 (2)	C18—H8B	1.01 (2)
C12—C13	1.407 (3)	C10—H7	0.98 (2)
C12—C11	1.478 (3)	C9—H6	0.98 (2)
N2—C9	1.316 (3)	C14—H5	0.954 (19)
N4—C18	1.468 (2)	C4—H4	0.98 (2)
N4—C21	1.471 (2)	C21—C20	1.519 (3)
C13—C14	1.372 (3)	C21—H3A	1.026 (18)
C13—H18	0.940 (19)	C21—H3B	1.03 (2)
C6—C5	1.394 (3)	C20—C19	1.519 (3)
C6—C1	1.406 (3)	C20—H2A	0.99 (2)
C6—C7	1.467 (2)	C20—H2B	1.01 (2)
C7—H15	1.004 (18)	C19—H1A	1.03 (2)
C3—C4	1.378 (3)	C19—H1B	0.98 (2)
C3—C2	1.384 (3)
C10—N3—N2	109.69 (16)	C2—C1—H10	119.7 (11)
C10—N3—C8	128.79 (17)	C6—C1—H10	120.2 (11)
N2—N3—C8	121.47 (15)	C16—C15—F1	117.59 (17)
C7—C8—N3	120.55 (16)	C16—C15—C14	124.80 (18)
C7—C8—C11	125.48 (17)	F1—C15—C14	117.60 (17)
N3—C8—C11	113.65 (15)	N4—C18—C19	103.35 (17)
C15—C16—C17	119.48 (19)	N4—C18—H8A	111.4 (10)
C15—C16—H23	119.3 (12)	C19—C18—H8A	111.9 (10)
C17—C16—H23	121.2 (12)	N4—C18—H8B	109.5 (11)
N4—C17—C16	118.64 (16)	C19—C18—H8B	112.8 (11)
N4—C17—C12	123.83 (16)	H8A—C18—H8B	107.9 (15)
C16—C17—C12	117.52 (17)	N1—C10—N3	110.9 (2)
C13—C12—C17	118.80 (17)	N1—C10—H7	128.5 (12)
C13—C12—C11	116.20 (16)	N3—C10—H7	120.6 (12)
C17—C12—C11	124.01 (16)	N2—C9—N1	115.8 (2)
C9—N2—N3	101.55 (17)	N2—C9—H6	120.1 (12)
C17—N4—C18	121.73 (16)	N1—C9—H6	124.1 (12)
C17—N4—C21	124.29 (15)	C13—C14—C15	115.96 (19)
C18—N4—C21	110.76 (15)	C13—C14—H5	123.1 (12)
C14—C13—C12	123.04 (19)	C15—C14—H5	120.9 (12)
C14—C13—H18	120.7 (11)	C3—C4—C5	120.1 (2)
C12—C13—H18	116.2 (11)	C3—C4—H4	120.3 (11)
C5—C6—C1	118.15 (17)	C5—C4—H4	119.6 (11)
C5—C6—C7	117.39 (17)	N4—C21—C20	104.23 (17)
C1—C6—C7	124.45 (18)	N4—C21—H3A	108.6 (10)
O1—C11—C12	122.52 (16)	C20—C21—H3A	113.9 (10)
O1—C11—C8	117.93 (16)	N4—C21—H3B	109.3 (12)
C12—C11—C8	119.47 (16)	C20—C21—H3B	112.6 (12)
C8—C7—C6	130.44 (18)	H3A—C21—H3B	108.0 (15)
C8—C7—H15	114.9 (10)	C21—C20—C19	103.03 (19)
C6—C7—H15	114.6 (10)	C21—C20—H2A	110.8 (11)
C4—C3—C2	119.69 (19)	C19—C20—H2A	112.1 (12)
C4—C3—H14	120.5 (12)	C21—C20—H2B	110.3 (12)
C2—C3—H14	119.8 (12)	C19—C20—H2B	114.9 (12)
C10—N1—C9	102.06 (18)	H2A—C20—H2B	105.9 (17)
C4—C5—C6	121.24 (19)	C20—C19—C18	102.69 (18)
C4—C5—H12	119.7 (11)	C20—C19—H1A	112.8 (12)
C6—C5—H12	119.1 (11)	C18—C19—H1A	110.9 (12)
C3—C2—C1	120.8 (2)	C20—C19—H1B	110.2 (14)
C3—C2—H11	122.7 (11)	C18—C19—H1B	110.3 (14)
C1—C2—H11	116.5 (12)	H1A—C19—H1B	109.8 (18)
C2—C1—C6	120.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H12···O1i	0.981 (19)	2.435 (19)	3.347 (2)	154.6 (14)
C16—H23···N1ii	0.906 (19)	2.525 (19)	3.388 (3)	159.3 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H12⋯O1i	0.981 (19)	2.435 (19)	3.347 (2)	154.6 (14)
C16—H23⋯N1ii	0.906 (19)	2.525 (19)	3.388 (3)	159.3 (16)

Symmetry codes: (i) ; (ii) .