(4-Fluoro-phen-yl)(1H-pyrrol-2-yl)methan-one.

In the title mol-ecule, C(11)H(8)FNO, the dihedral angle between the pyrrole and benzene rings is 49.16 (6)°. In the crystal, adjacent mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For background to pyrrole derivatives and their applications, see: Fischer & Orth (1934 ▶); Mohamed et al. (2009 ▶). For related structures, see: English et al. (1980 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H8FNO

M = 189.18

Triclinic,

a = 3.8957 (2) Å

b = 10.7053 (5) Å

c = 11.1421 (6) Å

α = 99.167 (4)°

β = 95.951 (4)°

γ = 98.699 (4)°

V = 449.56 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.980, T max = 1.000

10652 measured reflections

1762 independent reflections

1410 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.098

S = 1.03

1762 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction,2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812025871/gk2499sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025871/gk2499Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025871/gk2499Isup3.cml

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

C11H8FNO	Z = 2
Mr = 189.18	F(000) = 196
Triclinic, P1	Dx = 1.398 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.8957 (2) Å	Cell parameters from 4740 reflections
b = 10.7053 (5) Å	θ = 3.7–28.9°
c = 11.1421 (6) Å	µ = 0.11 mm−1
α = 99.167 (4)°	T = 293 K
β = 95.951 (4)°	Plate, white
γ = 98.699 (4)°	0.3 × 0.2 × 0.1 mm
V = 449.56 (4) Å3

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1762 independent reflections
Radiation source: fine-focus sealed tube	1410 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.7°
ω scan	h = −4→4
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −13→13
Tmin = 0.980, Tmax = 1.000	l = −13→13
10652 measured reflections

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0393P)2 + 0.1079P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
1762 reflections	Δρmax = 0.16 e Å−3
128 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.068 (8)

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.1668 (3)	0.83359 (12)	0.41956 (11)	0.0485 (3)
H1	0.0862	0.9039	0.4184	0.058*
C2	0.2594 (4)	0.78614 (13)	0.52317 (13)	0.0415 (3)
C3	0.3794 (4)	0.67263 (14)	0.48471 (15)	0.0474 (4)
H3	0.4618	0.6192	0.5350	0.057*
C4	0.3545 (4)	0.65312 (15)	0.35771 (15)	0.0538 (4)
H4	0.4169	0.5845	0.3074	0.065*
C5	0.2207 (4)	0.75399 (16)	0.32037 (14)	0.0543 (4)
H5	0.1750	0.7653	0.2396	0.065*
C6	0.2390 (4)	0.85622 (13)	0.64280 (14)	0.0428 (4)
O6	0.1574 (3)	0.96424 (10)	0.65746 (10)	0.0600 (4)
C7	0.3239 (4)	0.79769 (13)	0.75287 (13)	0.0414 (3)
C8	0.1941 (4)	0.67098 (14)	0.75797 (14)	0.0468 (4)
H8	0.0594	0.6185	0.6895	0.056*
C9	0.2626 (5)	0.62175 (16)	0.86362 (15)	0.0554 (4)
H9	0.1716	0.5373	0.8678	0.066*
C10	0.4675 (5)	0.70044 (18)	0.96151 (15)	0.0597 (5)
C11	0.6022 (5)	0.82580 (18)	0.96050 (15)	0.0619 (5)
H11	0.7410	0.8768	1.0290	0.074*
C12	0.5269 (4)	0.87470 (15)	0.85531 (15)	0.0525 (4)
H12	0.6130	0.9601	0.8531	0.063*
F1	0.5388 (4)	0.65272 (12)	1.06567 (9)	0.0951 (5)

	U11	U22	U33	U12	U13	U23
N1	0.0574 (8)	0.0403 (7)	0.0514 (8)	0.0120 (6)	0.0089 (6)	0.0141 (6)
C2	0.0402 (8)	0.0380 (8)	0.0473 (8)	0.0057 (6)	0.0047 (6)	0.0117 (6)
C3	0.0459 (8)	0.0416 (8)	0.0565 (9)	0.0120 (6)	0.0054 (7)	0.0106 (7)
C4	0.0548 (10)	0.0477 (9)	0.0577 (10)	0.0109 (7)	0.0114 (7)	0.0012 (7)
C5	0.0608 (10)	0.0544 (10)	0.0464 (9)	0.0065 (8)	0.0083 (7)	0.0077 (7)
C6	0.0426 (8)	0.0345 (7)	0.0526 (9)	0.0077 (6)	0.0069 (6)	0.0104 (6)
O6	0.0852 (9)	0.0397 (6)	0.0603 (7)	0.0228 (6)	0.0102 (6)	0.0122 (5)
C7	0.0420 (8)	0.0390 (8)	0.0453 (8)	0.0143 (6)	0.0065 (6)	0.0062 (6)
C8	0.0525 (9)	0.0410 (8)	0.0477 (9)	0.0120 (7)	0.0031 (7)	0.0087 (6)
C9	0.0711 (11)	0.0479 (9)	0.0543 (10)	0.0216 (8)	0.0121 (8)	0.0169 (8)
C10	0.0792 (12)	0.0679 (11)	0.0415 (9)	0.0392 (9)	0.0080 (8)	0.0131 (8)
C11	0.0695 (11)	0.0666 (12)	0.0460 (9)	0.0260 (9)	−0.0043 (8)	−0.0063 (8)
C12	0.0573 (10)	0.0433 (9)	0.0547 (10)	0.0129 (7)	0.0055 (7)	−0.0005 (7)
F1	0.1500 (12)	0.1005 (9)	0.0478 (6)	0.0585 (8)	0.0025 (7)	0.0240 (6)

N1—C5	1.339 (2)	C7—C8	1.386 (2)
N1—C2	1.3699 (18)	C7—C12	1.387 (2)
N1—H1	0.8600	C8—C9	1.382 (2)
C2—C3	1.388 (2)	C8—H8	0.9300
C2—C6	1.438 (2)	C9—C10	1.364 (3)
C3—C4	1.388 (2)	C9—H9	0.9300
C3—H3	0.9300	C10—F1	1.3602 (18)
C4—C5	1.371 (2)	C10—C11	1.367 (3)
C4—H4	0.9300	C11—C12	1.380 (2)
C5—H5	0.9300	C11—H11	0.9300
C6—O6	1.2357 (17)	C12—H12	0.9300
C6—C7	1.493 (2)
C5—N1—C2	109.79 (12)	C8—C7—C12	119.05 (14)
C5—N1—H1	125.1	C8—C7—C6	122.28 (13)
C2—N1—H1	125.1	C12—C7—C6	118.61 (13)
N1—C2—C3	106.57 (13)	C9—C8—C7	120.79 (15)
N1—C2—C6	120.91 (12)	C9—C8—H8	119.6
C3—C2—C6	132.43 (13)	C7—C8—H8	119.6
C2—C3—C4	107.76 (13)	C10—C9—C8	118.13 (15)
C2—C3—H3	126.1	C10—C9—H9	120.9
C4—C3—H3	126.1	C8—C9—H9	120.9
C5—C4—C3	107.18 (14)	F1—C10—C9	118.64 (17)
C5—C4—H4	126.4	F1—C10—C11	118.26 (16)
C3—C4—H4	126.4	C9—C10—C11	123.10 (15)
N1—C5—C4	108.69 (14)	C10—C11—C12	118.31 (15)
N1—C5—H5	125.7	C10—C11—H11	120.8
C4—C5—H5	125.7	C12—C11—H11	120.8
O6—C6—C2	121.97 (13)	C11—C12—C7	120.61 (15)
O6—C6—C7	118.92 (13)	C11—C12—H12	119.7
C2—C6—C7	119.11 (12)	C7—C12—H12	119.7
C5—N1—C2—C3	0.71 (17)	O6—C6—C7—C12	−42.0 (2)
C5—N1—C2—C6	177.63 (14)	C2—C6—C7—C12	137.16 (15)
N1—C2—C3—C4	−0.42 (17)	C12—C7—C8—C9	0.5 (2)
C6—C2—C3—C4	−176.84 (15)	C6—C7—C8—C9	−176.53 (14)
C2—C3—C4—C5	−0.01 (18)	C7—C8—C9—C10	−1.4 (2)
C2—N1—C5—C4	−0.73 (18)	C8—C9—C10—F1	−179.51 (14)
C3—C4—C5—N1	0.45 (19)	C8—C9—C10—C11	1.2 (3)
N1—C2—C6—O6	−4.2 (2)	F1—C10—C11—C12	−179.32 (15)
C3—C2—C6—O6	171.82 (16)	C9—C10—C11—C12	0.0 (3)
N1—C2—C6—C7	176.72 (13)	C10—C11—C12—C7	−0.9 (2)
C3—C2—C6—C7	−7.3 (2)	C8—C7—C12—C11	0.7 (2)
O6—C6—C7—C8	135.08 (16)	C6—C7—C12—C11	177.84 (14)
C2—C6—C7—C8	−45.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6i	0.86	2.06	2.865 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6i	0.86	2.06	2.865 (2)	157

Symmetry code: (i) .