(4-Fluoro­phen­yl)(1H-pyrrol-2-yl)methan­one

Prakash, V.; Kapoor, K.; Shet Prakash, M.; Gupta, V.K.; Kant, R.

doi:10.1107/S1600536812025871

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2073

https://doi.org/10.1107/S1600536812025871

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(4-Fluorophenyl)(1H-pyrrol-2-yl)methanone

V. Prakash,^a Kamini Kapoor,^b M. Shet Prakash,^c,^d Vivek K. Gupta ^b and Rajni Kant ^b ^*

^aShirdi Sai Engineering College, Anekal, Bangalore 562 106, India, ^bX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, ^cDepartment of Chemistry, University College of Science, Tumkur University, Tumkur, India, and ^dCentre for Advanced Materials, Tumkur University, Tumkur, India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 6 June 2012; accepted 7 June 2012; online 13 June 2012)

In the title molecule, C₁₁H₈FNO, the dihedral angle between the pyrrole and benzene rings is 49.16 (6)°. In the crystal, adjacent molecules 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_r = 189.18
Triclinic, $[P \overline 1]$
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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.098
S = 1.03
1762 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.15 e Å⁻³

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) -x, -y+2, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction,2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812025871/gk2499sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025871/gk2499Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025871/gk2499Isup3.cml

checkCIF report

Comment top

The chemistry of pyrrole compounds and biological activities of the related compounds have been extensively studied (Fischer & Orth, 1934; Mohamed et al., 2009). With the view of biological importance, the title compound was synthesized and its crystal structure is reported here.

Bond lengths and angles in the title compound (Fig. 1) have normal values (Allen et al., 1987) and are comparable with the similar crystal structures solved earlier (English et al., 1980). The pyrrole and benzene rings are planar with maximum deviations of 0.004 (2) Å and -0.009 (2) Å, respectively. The two rings are not coplanar with the dihedral angle being 49.16 (6)°. The crystal packing is stabilized by N—H···O intermolecular interactions, generating centrosymmetric dimers (Fig. 2).

Related literature top

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 top

Amide-phosphoryl complex was prepared by treating 1 equiv. of N,N-dimethyl-4-fluorobenzamide with 3 equiv. of POCl₃ at room temperature and stirred for 6 h. The above complex was treated with pyrrole in anhydrous 1,2-dichloroethane at 25°C and stirred for one hour and kept overnight. The resulting mixture was hydrolyzed using saturated sodium carbonate solution, followed by heating for 45 minutes to obtain the title compound. The title compound was extracted using 1,2-dichloroethane. Single crystals required for X-ray diffraction were obtained by slow evaporation of the methanolic solution of the compound.

Structure description top

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).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction,2010); cell refinement: CrysAlis PRO (Oxford Diffraction,2010); data reduction: CrysAlis PRO (Oxford Diffraction,2010); 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).

Figures top

	Fig. 1. ORTEP view of the molecule with the atom-labeling scheme. The thermal ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A molecular packing view of the title compound, showing intermolecular interactions. For clarity, hydrogen atoms which are not involved in hydrogen bonding have been omitted.

(4-Fluorophenyl)(1H-pyrrol-2-yl)methanone top

Crystal data top

C₁₁H₈FNO	Z = 2
M_r = 189.18	F(000) = 196
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.038	H-atom parameters constrained
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0393P)² + 0.1079P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
1762 reflections	Δρ_max = 0.16 e Å⁻³
128 parameters	Δρ_min = −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)

Crystal data top

C₁₁H₈FNO	γ = 98.699 (4)°
M_r = 189.18	V = 449.56 (4) Å³
Triclinic, P1	Z = 2
a = 3.8957 (2) Å	Mo Kα radiation
b = 10.7053 (5) Å	µ = 0.11 mm⁻¹
c = 11.1421 (6) Å	T = 293 K
α = 99.167 (4)°	0.3 × 0.2 × 0.1 mm
β = 95.951 (4)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1762 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	1410 reflections with I > 2σ(I)
T_min = 0.980, T_max = 1.000	R_int = 0.027
10652 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.03	Δρ_max = 0.16 e Å⁻³
1762 reflections	Δρ_min = −0.15 e Å⁻³
128 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₁H₈FNO
M_r	189.18
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	3.8957 (2), 10.7053 (5), 11.1421 (6)
α, β, γ (°)	99.167 (4), 95.951 (4), 98.699 (4)
V (Å³)	449.56 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.3 × 0.2 × 0.1

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.980, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10652, 1762, 1410
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.098, 1.03
No. of reflections	1762
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

Computer programs: CrysAlis PRO (Oxford Diffraction,2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x, −y+2, −z+1.

Acknowledgements

RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

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