4-[2-(4-Fluoro-phen-yl)-1H-pyrrol-3-yl]pyridine.

In the crystal structure of the title compound, C(15)H(11)FN(2), the pyrrole ring makes dihedral angles of 33.19 (9) and 36.33 (10)° with the pyridine and 4-fluoro-phenyl rings, respectively. The pyridine ring makes a dihedral angle of 46.59 (9)° with the 4-fluoro-phenyl ring. In the crystal structure, an N-H⋯N hydrogen bond joins the mol-ecules into chains.

Related literature

Many 1-(4-fluoro­phenyl)-2-(pyridin-4-yl)pyrrol derivatives have been prepared and their biological activities studied; see: de Laszlo et al. (1998 ▶); Revesz et al. (2000 ▶, 2002 ▶); Qian et al. (2006 ▶). For the synthesis of the title compound, see: Qian et al. (2006 ▶).

Experimental

Crystal data

C15H11FN2

M = 238.26

Orthorhombic,

a = 9.2966 (7) Å

b = 8.1966 (5) Å

c = 30.5738 (19) Å

V = 2329.7 (3) Å3

Z = 8

Cu Kα radiation

μ = 0.76 mm−1

T = 193 (2) K

0.25 × 0.20 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

2175 measured reflections

2175 independent reflections

1744 reflections with I > 2σ(I)

3 standard reflections frequency: 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 1.03

2175 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900364X/bt2858sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900364X/bt2858Isup2.hkl

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

C15H11FN2	F(000) = 992
Mr = 238.26	Dx = 1.359 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 9.2966 (7) Å	θ = 30–51.7°
b = 8.1966 (5) Å	µ = 0.76 mm−1
c = 30.5738 (19) Å	T = 193 K
V = 2329.7 (3) Å3	Plate, light brown
Z = 8	0.25 × 0.20 × 0.18 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.0000
Radiation source: rotating anode	θmax = 69.5°, θmin = 2.9°
graphite	h = 0→11
ω/2θ scans	k = −9→0
2175 measured reflections	l = −36→0
2175 independent reflections	3 standard reflections every 60 min
1744 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0641P)2 + 0.5148P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2175 reflections	Δρmax = 0.26 e Å−3
164 parameters	Δρmin = −0.17 e Å−3
0 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: 0.00086 (16)

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
N1	0.51524 (14)	0.21406 (17)	0.41905 (5)	0.0278 (3)
H1	0.6083	0.2266	0.4081	0.033*
C2	0.39066 (16)	0.2347 (2)	0.39570 (6)	0.0249 (4)
C3	0.27690 (16)	0.2008 (2)	0.42407 (5)	0.0255 (4)
C4	0.33869 (18)	0.1586 (2)	0.46491 (6)	0.0311 (4)
H4	0.2876	0.1288	0.4906	0.037*
C5	0.48474 (18)	0.1684 (2)	0.46075 (6)	0.0317 (4)
H5	0.5531	0.1470	0.4831	0.038*
C6	0.39610 (16)	0.2800 (2)	0.34938 (5)	0.0264 (4)
C7	0.50091 (18)	0.3890 (2)	0.33407 (6)	0.0331 (4)
H7	0.5698	0.4322	0.3539	0.040*
C8	0.5055 (2)	0.4345 (3)	0.29053 (6)	0.0421 (5)
H8	0.5773	0.5075	0.2802	0.051*
C9	0.4047 (2)	0.3721 (3)	0.26266 (6)	0.0429 (5)
C10	0.3009 (2)	0.2630 (3)	0.27593 (6)	0.0395 (5)
H10	0.2329	0.2207	0.2557	0.047*
C11	0.29785 (18)	0.2163 (2)	0.31936 (6)	0.0311 (4)
H11	0.2279	0.1397	0.3289	0.037*
F12	0.40632 (16)	0.4201 (2)	0.22006 (4)	0.0706 (5)
C13	0.12145 (16)	0.20955 (19)	0.41599 (5)	0.0244 (4)
C14	0.05747 (18)	0.3235 (2)	0.38834 (6)	0.0292 (4)
H14	0.1155	0.3991	0.3727	0.035*
C15	−0.09026 (18)	0.3267 (2)	0.38362 (6)	0.0318 (4)
H15	−0.1307	0.4053	0.3644	0.038*
N16	−0.17994 (14)	0.2253 (2)	0.40458 (5)	0.0329 (4)
C17	−0.11823 (18)	0.1169 (2)	0.43157 (6)	0.0320 (4)
H17	−0.1791	0.0442	0.4472	0.038*
C18	0.02834 (17)	0.1046 (2)	0.43807 (5)	0.0286 (4)
H18	0.0657	0.0248	0.4575	0.034*

	U11	U22	U33	U12	U13	U23
N1	0.0166 (6)	0.0319 (8)	0.0348 (8)	−0.0002 (6)	−0.0004 (5)	0.0008 (6)
C2	0.0176 (7)	0.0249 (8)	0.0322 (9)	0.0008 (6)	0.0008 (6)	−0.0021 (6)
C3	0.0207 (8)	0.0253 (8)	0.0304 (8)	−0.0006 (6)	0.0015 (6)	−0.0009 (7)
C4	0.0258 (8)	0.0379 (10)	0.0297 (9)	0.0005 (7)	0.0018 (7)	0.0050 (7)
C5	0.0266 (8)	0.0359 (10)	0.0327 (9)	0.0011 (7)	−0.0036 (7)	0.0037 (7)
C6	0.0199 (7)	0.0276 (8)	0.0316 (9)	0.0044 (6)	0.0034 (6)	−0.0020 (6)
C7	0.0267 (8)	0.0374 (10)	0.0353 (9)	−0.0029 (7)	0.0064 (7)	−0.0013 (7)
C8	0.0413 (10)	0.0452 (11)	0.0399 (10)	−0.0017 (9)	0.0160 (9)	0.0048 (8)
C9	0.0483 (11)	0.0538 (12)	0.0266 (9)	0.0098 (10)	0.0091 (8)	0.0025 (8)
C10	0.0377 (10)	0.0475 (11)	0.0332 (10)	0.0072 (9)	−0.0022 (8)	−0.0071 (8)
C11	0.0253 (8)	0.0342 (9)	0.0339 (9)	0.0030 (7)	0.0007 (7)	−0.0027 (7)
F12	0.0869 (11)	0.0956 (11)	0.0292 (6)	−0.0015 (9)	0.0080 (6)	0.0113 (7)
C13	0.0204 (8)	0.0262 (8)	0.0264 (8)	−0.0003 (6)	0.0028 (6)	−0.0052 (6)
C14	0.0226 (8)	0.0289 (9)	0.0361 (9)	0.0001 (7)	0.0041 (7)	0.0013 (7)
C15	0.0232 (8)	0.0343 (9)	0.0380 (10)	0.0042 (7)	0.0013 (7)	0.0012 (8)
N16	0.0197 (7)	0.0426 (9)	0.0362 (8)	0.0000 (6)	0.0031 (6)	−0.0027 (7)
C17	0.0237 (8)	0.0384 (10)	0.0339 (9)	−0.0049 (7)	0.0065 (7)	0.0000 (7)
C18	0.0244 (8)	0.0326 (9)	0.0286 (8)	−0.0009 (7)	0.0025 (6)	0.0005 (7)

N1—C5	1.358 (2)	C9—F12	1.360 (2)
N1—C2	1.371 (2)	C9—C10	1.377 (3)
N1—H1	0.9339	C10—C11	1.382 (3)
C2—C3	1.396 (2)	C10—H10	0.9500
C2—C6	1.465 (2)	C11—H11	0.9500
C3—C4	1.417 (2)	C13—C14	1.393 (2)
C3—C13	1.468 (2)	C13—C18	1.395 (2)
C4—C5	1.366 (2)	C14—C15	1.381 (2)
C4—H4	0.9500	C14—H14	0.9500
C5—H5	0.9500	C15—N16	1.340 (2)
C6—C11	1.396 (2)	C15—H15	0.9500
C6—C7	1.402 (2)	N16—C17	1.341 (2)
C7—C8	1.383 (3)	C17—C18	1.381 (2)
C7—H7	0.9500	C17—H17	0.9500
C8—C9	1.366 (3)	C18—H18	0.9500
C8—H8	0.9500
C5—N1—C2	110.27 (14)	F12—C9—C10	118.54 (19)
C5—N1—H1	124.1	C8—C9—C10	122.70 (18)
C2—N1—H1	125.6	C9—C10—C11	118.50 (18)
N1—C2—C3	106.96 (15)	C9—C10—H10	120.8
N1—C2—C6	120.37 (14)	C11—C10—H10	120.8
C3—C2—C6	132.65 (15)	C10—C11—C6	120.97 (17)
C2—C3—C4	106.80 (14)	C10—C11—H11	119.5
C2—C3—C13	129.17 (15)	C6—C11—H11	119.5
C4—C3—C13	124.00 (15)	C14—C13—C18	116.25 (15)
C5—C4—C3	107.84 (15)	C14—C13—C3	123.73 (15)
C5—C4—H4	126.1	C18—C13—C3	119.96 (15)
C3—C4—H4	126.1	C15—C14—C13	120.04 (16)
N1—C5—C4	108.13 (15)	C15—C14—H14	120.0
N1—C5—H5	125.9	C13—C14—H14	120.0
C4—C5—H5	125.9	N16—C15—C14	123.85 (17)
C11—C6—C7	118.26 (16)	N16—C15—H15	118.1
C11—C6—C2	121.19 (15)	C14—C15—H15	118.1
C7—C6—C2	120.55 (15)	C15—N16—C17	116.02 (14)
C8—C7—C6	120.96 (18)	N16—C17—C18	123.98 (16)
C8—C7—H7	119.5	N16—C17—H17	118.0
C6—C7—H7	119.5	C18—C17—H17	118.0
C9—C8—C7	118.57 (18)	C17—C18—C13	119.86 (16)
C9—C8—H8	120.7	C17—C18—H18	120.1
C7—C8—H8	120.7	C13—C18—H18	120.1
F12—C9—C8	118.76 (19)
C5—N1—C2—C3	0.13 (19)	C7—C8—C9—C10	−1.6 (3)
C5—N1—C2—C6	−178.44 (15)	F12—C9—C10—C11	−178.99 (17)
N1—C2—C3—C4	−0.29 (18)	C8—C9—C10—C11	0.8 (3)
C6—C2—C3—C4	178.03 (17)	C9—C10—C11—C6	1.0 (3)
N1—C2—C3—C13	177.86 (16)	C7—C6—C11—C10	−1.9 (2)
C6—C2—C3—C13	−3.8 (3)	C2—C6—C11—C10	178.16 (16)
C2—C3—C4—C5	0.4 (2)	C2—C3—C13—C14	−33.5 (3)
C13—C3—C4—C5	−177.92 (16)	C4—C3—C13—C14	144.40 (18)
C2—N1—C5—C4	0.1 (2)	C2—C3—C13—C18	149.46 (17)
C3—C4—C5—N1	−0.3 (2)	C4—C3—C13—C18	−32.7 (2)
N1—C2—C6—C11	142.67 (16)	C18—C13—C14—C15	−0.8 (2)
C3—C2—C6—C11	−35.5 (3)	C3—C13—C14—C15	−177.95 (16)
N1—C2—C6—C7	−37.2 (2)	C13—C14—C15—N16	0.4 (3)
C3—C2—C6—C7	144.63 (19)	C14—C15—N16—C17	0.3 (3)
C11—C6—C7—C8	1.1 (3)	C15—N16—C17—C18	−0.7 (3)
C2—C6—C7—C8	−178.99 (17)	N16—C17—C18—C13	0.3 (3)
C6—C7—C8—C9	0.6 (3)	C14—C13—C18—C17	0.4 (2)
C7—C8—C9—F12	178.17 (18)	C3—C13—C18—C17	177.73 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N16i	0.93	1.97	2.8696 (19)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N16i	0.93	1.97	2.8696 (19)	161

Symmetry code: (i) .