1-(2-Chloro-phenyl)-6-fluoro-2-methyl-1H-indole-3-carbonitrile.

In the title compound, C(16)H(10)ClFN(2), the dihedral angle between the indole ring system and the benzyl ring is 80.91 (5)°. The crystal packing features C-H⋯Cl, C-H⋯F and C-H⋯π inter-actions.

Related literature

For the synthesis of the title compound, see: Du et al. (2006 ▶). For its precursor, see: Jin et al. (2009 ▶). For related structures, see: Li & Huang (2009 ▶); Li et al. (2009 ▶, 2010a ▶,b ▶).

Experimental

Crystal data

C16H10ClFN2

M = 284.71

Orthorhombic,

a = 7.4581 (9) Å

b = 16.8480 (15) Å

c = 21.356 (2) Å

V = 2683.5 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 113 K

0.26 × 0.22 × 0.20 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2009 ▶) T min = 0.929, T max = 0.945

28426 measured reflections

3893 independent reflections

3219 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.11

3893 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2009 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2009 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011214/hb5823sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011214/hb5823Isup2.hkl

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

C16H10ClFN2	F(000) = 1168
Mr = 284.71	Dx = 1.409 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 10281 reflections
a = 7.4581 (9) Å	θ = 1.5–31.4°
b = 16.8480 (15) Å	µ = 0.29 mm−1
c = 21.356 (2) Å	T = 113 K
V = 2683.5 (5) Å3	Prism, colorless
Z = 8	0.26 × 0.22 × 0.20 mm

Rigaku Saturn724 CCD diffractometer	3893 independent reflections
Radiation source: rotating anode	3219 reflections with I > 2σ(I)
multilayer	Rint = 0.034
Detector resolution: 14.222 pixels mm-1	θmax = 30.0°, θmin = 1.9°
ω scans	h = −10→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009)	k = −23→23
Tmin = 0.929, Tmax = 0.945	l = −30→30
28426 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0644P)2 + 0.1004P] where P = (Fo2 + 2Fc2)/3
3893 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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
Cl1	0.50520 (4)	0.220294 (19)	0.641958 (16)	0.03226 (11)
F1	0.61121 (11)	0.54670 (5)	0.76153 (4)	0.0480 (2)
N1	0.39260 (12)	0.37712 (5)	0.59488 (4)	0.0236 (2)
N2	0.79477 (16)	0.43384 (7)	0.42798 (6)	0.0420 (3)
C1	0.45553 (17)	0.36559 (7)	0.53489 (5)	0.0258 (2)
C2	0.60108 (16)	0.41469 (7)	0.52619 (6)	0.0271 (3)
C3	0.63160 (15)	0.45816 (7)	0.58328 (6)	0.0265 (3)
C4	0.49938 (14)	0.43272 (7)	0.62558 (6)	0.0237 (2)
C5	0.48747 (16)	0.46061 (7)	0.68659 (6)	0.0280 (3)
H5	0.3986	0.4427	0.7151	0.034*
C6	0.61408 (17)	0.51607 (7)	0.70243 (6)	0.0337 (3)
C7	0.74735 (17)	0.54359 (8)	0.66235 (7)	0.0361 (3)
H7	0.8315	0.5819	0.6765	0.043*
C8	0.75667 (16)	0.51503 (7)	0.60210 (7)	0.0318 (3)
H8	0.8460	0.5336	0.5740	0.038*
C9	0.36953 (19)	0.30813 (8)	0.49124 (6)	0.0333 (3)
H9A	0.3812	0.2543	0.5081	0.040*
H9B	0.4286	0.3109	0.4503	0.040*
H9C	0.2423	0.3213	0.4866	0.040*
C10	0.70533 (17)	0.42350 (7)	0.47083 (6)	0.0317 (3)
C11	0.25337 (16)	0.33290 (7)	0.62467 (5)	0.0223 (2)
C12	0.28935 (15)	0.25756 (7)	0.64802 (5)	0.0230 (2)
C13	0.15588 (16)	0.21330 (7)	0.67690 (5)	0.0271 (3)
H13	0.1800	0.1612	0.6918	0.032*
C14	−0.01309 (16)	0.24642 (8)	0.68363 (6)	0.0277 (3)
H14	−0.1052	0.2169	0.7037	0.033*
C15	−0.04958 (18)	0.32238 (7)	0.66141 (6)	0.0295 (3)
H15	−0.1658	0.3446	0.6664	0.035*
C16	0.08411 (16)	0.36557 (7)	0.63194 (6)	0.0276 (3)
H16	0.0598	0.4175	0.6167	0.033*

	U11	U22	U33	U12	U13	U23
Cl1	0.02051 (19)	0.02941 (18)	0.0468 (2)	0.00492 (11)	0.00001 (12)	0.00824 (12)
F1	0.0450 (5)	0.0454 (5)	0.0535 (5)	−0.0100 (4)	−0.0018 (4)	−0.0201 (4)
N1	0.0198 (5)	0.0213 (4)	0.0298 (5)	−0.0031 (4)	0.0030 (4)	0.0022 (4)
N2	0.0363 (7)	0.0436 (7)	0.0461 (6)	0.0006 (5)	0.0128 (5)	0.0089 (5)
C1	0.0240 (6)	0.0243 (5)	0.0290 (5)	0.0016 (5)	0.0019 (5)	0.0054 (4)
C2	0.0218 (6)	0.0250 (5)	0.0344 (6)	0.0014 (4)	0.0040 (5)	0.0079 (5)
C3	0.0199 (6)	0.0210 (5)	0.0385 (6)	0.0020 (4)	0.0007 (5)	0.0081 (4)
C4	0.0178 (6)	0.0181 (5)	0.0353 (6)	0.0001 (4)	−0.0013 (4)	0.0036 (4)
C5	0.0234 (6)	0.0230 (6)	0.0376 (6)	−0.0001 (4)	0.0013 (5)	0.0006 (5)
C6	0.0311 (7)	0.0253 (6)	0.0446 (7)	0.0007 (5)	−0.0046 (6)	−0.0057 (5)
C7	0.0267 (7)	0.0220 (6)	0.0597 (8)	−0.0050 (5)	−0.0061 (6)	0.0016 (6)
C8	0.0199 (6)	0.0225 (6)	0.0528 (7)	−0.0007 (4)	0.0011 (6)	0.0100 (5)
C9	0.0349 (7)	0.0345 (7)	0.0304 (6)	−0.0037 (6)	0.0011 (5)	0.0007 (5)
C10	0.0259 (7)	0.0291 (6)	0.0402 (6)	0.0026 (5)	0.0047 (5)	0.0088 (5)
C11	0.0194 (6)	0.0216 (5)	0.0259 (5)	−0.0029 (4)	0.0004 (4)	0.0022 (4)
C12	0.0188 (6)	0.0235 (5)	0.0267 (5)	0.0008 (4)	−0.0021 (4)	0.0014 (4)
C13	0.0263 (6)	0.0255 (5)	0.0295 (5)	−0.0022 (5)	−0.0015 (5)	0.0070 (4)
C14	0.0230 (6)	0.0324 (6)	0.0275 (5)	−0.0069 (5)	0.0020 (5)	0.0031 (5)
C15	0.0199 (6)	0.0318 (6)	0.0369 (6)	0.0006 (5)	0.0032 (5)	−0.0002 (5)
C16	0.0229 (6)	0.0241 (6)	0.0358 (6)	0.0015 (5)	0.0009 (5)	0.0041 (5)

Cl1—C12	1.7328 (12)	C7—C8	1.375 (2)
F1—C6	1.3636 (15)	C7—H7	0.9500
N1—C1	1.3780 (15)	C8—H8	0.9500
N1—C4	1.3934 (14)	C9—H9A	0.9800
N1—C11	1.4276 (14)	C9—H9B	0.9800
N2—C10	1.1457 (16)	C9—H9C	0.9800
C1—C2	1.3775 (16)	C11—C16	1.3857 (16)
C1—C9	1.4892 (17)	C11—C12	1.3900 (15)
C2—C10	1.4227 (17)	C12—C13	1.3883 (16)
C2—C3	1.4404 (18)	C13—C14	1.3857 (17)
C3—C8	1.3963 (17)	C13—H13	0.9500
C3—C4	1.4045 (16)	C14—C15	1.3918 (18)
C4—C5	1.3879 (18)	C14—H14	0.9500
C5—C6	1.3708 (17)	C15—C16	1.3855 (17)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.3914 (19)	C16—H16	0.9500
C1—N1—C4	109.73 (9)	C3—C8—H8	120.8
C1—N1—C11	126.05 (10)	C1—C9—H9A	109.5
C4—N1—C11	123.83 (9)	C1—C9—H9B	109.5
C2—C1—N1	108.01 (10)	H9A—C9—H9B	109.5
C2—C1—C9	130.19 (11)	C1—C9—H9C	109.5
N1—C1—C9	121.80 (11)	H9A—C9—H9C	109.5
C1—C2—C10	127.27 (12)	H9B—C9—H9C	109.5
C1—C2—C3	108.40 (10)	N2—C10—C2	176.12 (15)
C10—C2—C3	124.33 (11)	C16—C11—C12	119.89 (10)
C8—C3—C4	119.56 (12)	C16—C11—N1	120.35 (10)
C8—C3—C2	134.28 (11)	C12—C11—N1	119.73 (10)
C4—C3—C2	106.16 (10)	C13—C12—C11	120.76 (11)
C5—C4—N1	129.26 (11)	C13—C12—Cl1	120.31 (9)
C5—C4—C3	123.06 (11)	C11—C12—Cl1	118.91 (9)
N1—C4—C3	107.68 (11)	C14—C13—C12	118.81 (11)
C6—C5—C4	114.73 (11)	C14—C13—H13	120.6
C6—C5—H5	122.6	C12—C13—H13	120.6
C4—C5—H5	122.6	C13—C14—C15	120.85 (11)
F1—C6—C5	118.39 (12)	C13—C14—H14	119.6
F1—C6—C7	117.04 (11)	C15—C14—H14	119.6
C5—C6—C7	124.57 (13)	C16—C15—C14	119.80 (12)
C8—C7—C6	119.68 (12)	C16—C15—H15	120.1
C8—C7—H7	120.2	C14—C15—H15	120.1
C6—C7—H7	120.2	C15—C16—C11	119.86 (11)
C7—C8—C3	118.39 (12)	C15—C16—H16	120.1
C7—C8—H8	120.8	C11—C16—H16	120.1
C4—N1—C1—C2	−1.08 (13)	C4—C5—C6—C7	−0.48 (18)
C11—N1—C1—C2	−174.11 (10)	F1—C6—C7—C8	−179.81 (11)
C4—N1—C1—C9	178.91 (11)	C5—C6—C7—C8	0.4 (2)
C11—N1—C1—C9	5.89 (17)	C6—C7—C8—C3	−0.63 (18)
N1—C1—C2—C10	−178.61 (11)	C4—C3—C8—C7	0.91 (17)
C9—C1—C2—C10	1.4 (2)	C2—C3—C8—C7	−178.87 (13)
N1—C1—C2—C3	0.59 (13)	C1—C2—C10—N2	177 (100)
C9—C1—C2—C3	−179.40 (12)	C3—C2—C10—N2	−2(2)
C1—C2—C3—C8	179.90 (13)	C1—N1—C11—C16	−104.36 (13)
C10—C2—C3—C8	−0.9 (2)	C4—N1—C11—C16	83.56 (14)
C1—C2—C3—C4	0.10 (13)	C1—N1—C11—C12	77.42 (15)
C10—C2—C3—C4	179.33 (11)	C4—N1—C11—C12	−94.66 (13)
C1—N1—C4—C5	−178.37 (12)	C16—C11—C12—C13	2.09 (17)
C11—N1—C4—C5	−5.16 (18)	N1—C11—C12—C13	−179.69 (10)
C1—N1—C4—C3	1.15 (13)	C16—C11—C12—Cl1	−176.62 (9)
C11—N1—C4—C3	174.36 (10)	N1—C11—C12—Cl1	1.61 (15)
C8—C3—C4—C5	−1.03 (17)	C11—C12—C13—C14	−1.76 (17)
C2—C3—C4—C5	178.81 (11)	Cl1—C12—C13—C14	176.93 (9)
C8—C3—C4—N1	179.41 (10)	C12—C13—C14—C15	0.59 (18)
C2—C3—C4—N1	−0.75 (12)	C13—C14—C15—C16	0.24 (19)
N1—C4—C5—C6	−179.77 (11)	C14—C15—C16—C11	0.07 (19)
C3—C4—C5—C6	0.78 (17)	C12—C11—C16—C15	−1.22 (17)
C4—C5—C6—F1	179.77 (11)	N1—C11—C16—C15	−179.44 (11)

Cg1 is the centroid of the C3–C8 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···F1i	0.95	2.54	3.1638 (16)	123
C7—H7···Cl1ii	0.95	2.73	3.5296 (14)	142
C15—H15···Cg1iii	0.95	2.92	3.7246 (14)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C8 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯F1i	0.95	2.54	3.1638 (16)	123
C7—H7⋯Cl1ii	0.95	2.73	3.5296 (14)	142
C15—H15⋯Cg1iii	0.95	2.92	3.7246 (14)	143

Symmetry codes: (i) ; (ii) ; (iii) .