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

Wen, Q.-M.; Yin, B.-T.; Yan, C.-Y.; Zhou, C.-H.

doi:10.1107/S1600536812018454

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1642

doi:10.1107/S1600536812018454

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

Qin-Mei Wen,^a Ben-Tao Yin,^a Cong-Yan Yan ^a and Cheng-He Zhou ^a ^*

^aLaboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China
^*Correspondence e-mail: zhouch@swu.edu.cn

(Received 5 March 2012; accepted 25 April 2012; online 5 May 2012)

In the title molecule, C₂₁H₁₉FN₄O, 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 molecules 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_r = 362.40
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.118
S = 1.05
3403 reflections
321 parameters
2 restraints
All H-atom parameters refined
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

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).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812018454/lh5432sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812018454/lh5432Isup3.cml

checkCIF report

Comment top

Chalcones are an important type of biologically active compounds with a diarylenone structural unit (Solankee et al., 2010). Triazole compounds have been shown to have clinical uses (Wang et al., 2011; Zhou et al., 2012; Chang et al., 2011). Our group have been contributing to the research and development of triazolyl chalcones as potential antimicrobial agents. Related structures of triazolylchalcones have alreay been reported (Wang et al., 2009; Yan et al., 2009). Herein we report the crystal structure of the title compound (I).

In the molecular structure (Fig. 1) the triazole ring [N1/N2/N3/C9/C10] forms dihedral angles of 67.0 (1) and 59.6 (1)° with the phenyl [C1-C6] and fluoro-substituted benzene [C12-C17] rings. The dihedral angles between the phenyl and fluoro-substituted bezene rings is 79.1 (1)°. The pyrrolidine ring [N4/C18-C21] is in a half-chair conformation. In the crystal, weak C—H···O and C—H···N hydrogen bonds connect molecules into layers parallel to (001).

Related literature top

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 top

The title compound (I) was synthesized according to the procedure of Solankee et al. (2010). To a stirring mixture of 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (2.23 g, 10 mmol) and benzaldehyde (1.06 g, 10 mmol) in ethanol (20 mL) in the presence of acetic acid (0.08 mL, 1.4 mmol) was added pyrrolidine (0.71 g, 10 mmol). The mixed solution was refluxed until the reaction came to the end (monitored by TLC). Subsequently, the solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane (20 mL) and extracted with water (3 x 20 mL). The combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to produce the crude product, which was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (15/1:1/1, V/V) to afford the desired compound. A crystal suitable for X-ray analysis was grown from a solution of (I) in petroleum ether and ethyl acetate by slow evaporation at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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).

Figures top

Fig. 1. Ellipsoid plot.

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

Crystal data top

C₂₁H₁₉FN₄O	Z = 4
M_r = 362.40	F(000) = 760
Monoclinic, P2₁/c	D_x = 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

Data collection top

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

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)] = 0.048	All H-atom parameters refined
wR(F²) = 0.118	w = 1/[σ²(F_o²) + (0.0576P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3403 reflections	Δρ_max = 0.23 e Å⁻³
321 parameters	Δρ_min = −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)

Crystal data top

C₂₁H₁₉FN₄O	V = 1778.0 (6) Å³
M_r = 362.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.217 (2) Å	µ = 0.09 mm⁻¹
b = 10.067 (2) Å	T = 173 K
c = 15.793 (3) Å	0.30 × 0.08 × 0.03 mm
β = 94.47 (3)°

Data collection top

Bruker SMART CCD diffractometer	3403 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2341 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.997	R_int = 0.058
13447 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	2 restraints
wR(F²) = 0.118	All H-atom parameters refined
S = 1.05	Δρ_max = 0.23 e Å⁻³
3403 reflections	Δρ_min = −0.19 e Å⁻³
321 parameters

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	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₉FN₄O
M_r	362.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	11.217 (2), 10.067 (2), 15.793 (3)
β (°)	94.47 (3)
V (Å³)	1778.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.08 × 0.03

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.973, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	13447, 3403, 2341
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.118, 1.05
No. of reflections	3403
No. of parameters	321
No. of restraints	2
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.19

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2; (ii) x−1, y, z.

Acknowledgements

This work was partially supported by the Natural Science Foundation of China (21172181) and the Research Funds for the Central Universities, the key program of the Natural Science Foundation of Chongqing (CSTC2012jjB10026), the Specialized Research Fund for the Doctoral Program of Higher Education of China (SRFDP 20110182110007) and the Research Funds for the Central Universities (XDJK2011D007, XDJK2012B026).

References

Bruker (1997). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chang, J.-J., Wang, Y., Zhang, H.-Z., Zhou, C.-H., Geng, R.-X. & Ji, Q.-G. (2011). Chem. J. Chin. Univ. 32, 1970–1985. CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Solankee, A., Kapadia, K., Ćirić, A., Soković, M., Doytchinova, I. & Geronikaki, A. (2010). Eur. J. Med. Chem. 45, 510–518. Web of Science CrossRef PubMed CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, G., Lu, Y., Zhou, C. & Zhang, Y. (2009). Acta Cryst. E65, o1113. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, Y. & Zhou, C.-H. (2011). Sci. Sin. Chim, 41, 1429–1456. CrossRef Google Scholar
Yan, C.-Y., Wang, G.-Z. & Zhou, C.-H. (2009). Acta Cryst. E65, o2054. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhou, C.-H. & Wang, Y. (2012). Curr. Med. Chem. 19, 239–280. Web of Science CAS PubMed Google Scholar

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Volume 68| Part 6| June 2012| Page o1642

doi:10.1107/S1600536812018454

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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