1-(4-Chloro-3-fluoro-phen-yl)-2-[(3-phenyl-isoquinolin-1-yl)sulfan-yl]ethanone.

In the title compound, C(23)H(15)ClFNOS, the isoquinoline system and the 4-chloro-3-fluoro-phenyl ring are aligned at 80.4 (1)°. The dihedral angle between the isoquinoline system and the pendant (unsubstituted) phenyl ring is 19.91 (1)°.

Related literature

For related structures, see: Hathwar et al. (2008 ▶); Manivel et al. (2009a ▶,b ▶).

Experimental

Crystal data

C23H15ClFNOS

M = 407.87

Orthorhombic,

a = 16.9008 (11) Å

b = 9.8036 (7) Å

c = 23.3226 (16) Å

V = 3864.3 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 290 (2) K

0.24 × 0.18 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.925, T max = 0.965

27428 measured reflections

3595 independent reflections

2424 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.128

S = 1.04

3595 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia,1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001573/ng2534sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001573/ng2534Isup2.hkl

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

C23H15ClFNOS	F(000) = 1680
Mr = 407.87	Dx = 1.402 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3595 reflections
a = 16.9008 (11) Å	θ = 1.8–25.5°
b = 9.8036 (7) Å	µ = 0.33 mm−1
c = 23.3226 (16) Å	T = 290 K
V = 3864.3 (5) Å3	Block, colourless
Z = 8	0.24 × 0.18 × 0.11 mm

Bruker SMART CCD area-detector diffractometer	3595 independent reflections
Radiation source: fine-focus sealed tube	2424 reflections with I > 2σ(I)
graphite	Rint = 0.063
φ and ω scans	θmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→20
Tmin = 0.925, Tmax = 0.965	k = −11→11
27428 measured reflections	l = −28→28

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0566P)2 + 1.1665P] where P = (Fo2 + 2Fc2)/3
3595 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.19 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.

	x	y	z	Uiso*/Ueq
O1	0.07142 (12)	0.8183 (2)	0.28005 (9)	0.0633 (6)
F1	0.09785 (13)	0.8393 (2)	0.06905 (9)	0.1057 (7)
S1	0.03138 (4)	0.61721 (7)	0.37120 (3)	0.0495 (2)
Cl1	−0.02952 (8)	0.70329 (14)	0.00961 (4)	0.1221 (5)
N1	0.12270 (12)	0.4853 (2)	0.29715 (9)	0.0399 (5)
C1	0.11497 (15)	0.5201 (2)	0.35092 (11)	0.0393 (6)
C2	0.18572 (14)	0.4054 (2)	0.28104 (11)	0.0405 (6)
C3	0.24276 (16)	0.3684 (3)	0.31906 (11)	0.0474 (7)
H3	0.2861	0.3180	0.3066	0.057*
C4	0.29398 (18)	0.3701 (3)	0.41884 (13)	0.0593 (8)
H4	0.3384	0.3205	0.4079	0.071*
C5	0.2845 (2)	0.4076 (3)	0.47468 (14)	0.0688 (9)
H5	0.3225	0.3827	0.5016	0.083*
C6	0.2188 (2)	0.4828 (3)	0.49197 (13)	0.0643 (9)
H6	0.2135	0.5085	0.5302	0.077*
C7	0.16226 (18)	0.5189 (3)	0.45299 (12)	0.0538 (7)
H7	0.1180	0.5676	0.4650	0.065*
C8	0.17027 (16)	0.4832 (2)	0.39492 (11)	0.0422 (6)
C9	0.23657 (16)	0.4063 (3)	0.37753 (11)	0.0451 (6)
C10	0.18550 (14)	0.3638 (2)	0.21970 (11)	0.0419 (6)
C11	0.13897 (17)	0.4309 (3)	0.18011 (12)	0.0515 (7)
H11	0.1085	0.5046	0.1921	0.062*
C12	0.13641 (19)	0.3920 (3)	0.12340 (12)	0.0597 (8)
H12	0.1046	0.4392	0.0976	0.072*
C13	0.18110 (19)	0.2828 (3)	0.10499 (13)	0.0641 (9)
H13	0.1805	0.2569	0.0666	0.077*
C14	0.22641 (19)	0.2130 (4)	0.14375 (14)	0.0715 (10)
H14	0.2556	0.1379	0.1317	0.086*
C15	0.22938 (17)	0.2524 (3)	0.20044 (13)	0.0598 (8)
H15	0.2609	0.2042	0.2261	0.072*
C16	−0.01524 (15)	0.6351 (3)	0.30300 (11)	0.0439 (6)
H16A	−0.0177	0.5461	0.2849	0.053*
H16B	−0.0692	0.6659	0.3089	0.053*
C17	0.02538 (15)	0.7327 (2)	0.26264 (12)	0.0426 (6)
C18	0.00791 (15)	0.7226 (2)	0.20013 (12)	0.0422 (6)
C19	0.05916 (17)	0.7874 (3)	0.16253 (13)	0.0520 (7)
H19	0.1020	0.8366	0.1766	0.062*
C20	0.0465 (2)	0.7788 (3)	0.10523 (15)	0.0647 (9)
C21	−0.0164 (2)	0.7098 (4)	0.08298 (14)	0.0679 (9)
C22	−0.0680 (2)	0.6464 (3)	0.11953 (15)	0.0714 (9)
H22	−0.1116	0.6000	0.1049	0.086*
C23	−0.05585 (18)	0.6510 (3)	0.17826 (13)	0.0572 (8)
H23	−0.0904	0.6062	0.2029	0.069*

	U11	U22	U33	U12	U13	U23
O1	0.0674 (14)	0.0532 (12)	0.0694 (14)	−0.0142 (11)	−0.0162 (11)	−0.0004 (10)
F1	0.1066 (17)	0.1363 (19)	0.0742 (14)	−0.0033 (15)	0.0267 (12)	0.0272 (13)
S1	0.0554 (5)	0.0517 (4)	0.0412 (4)	0.0142 (3)	0.0010 (3)	−0.0073 (3)
Cl1	0.1660 (12)	0.1504 (11)	0.0500 (6)	0.0166 (9)	−0.0195 (6)	0.0006 (6)
N1	0.0408 (13)	0.0394 (12)	0.0396 (12)	0.0018 (10)	0.0016 (10)	−0.0030 (9)
C1	0.0454 (16)	0.0322 (13)	0.0404 (15)	−0.0012 (11)	0.0021 (12)	−0.0003 (11)
C2	0.0372 (15)	0.0380 (14)	0.0462 (15)	−0.0010 (11)	0.0047 (12)	−0.0020 (12)
C3	0.0381 (15)	0.0473 (15)	0.0570 (17)	0.0062 (12)	0.0002 (14)	−0.0042 (14)
C4	0.0579 (19)	0.0559 (18)	0.064 (2)	0.0096 (15)	−0.0138 (16)	0.0034 (16)
C5	0.081 (2)	0.068 (2)	0.058 (2)	0.0080 (19)	−0.0261 (18)	0.0111 (17)
C6	0.090 (2)	0.0590 (19)	0.0443 (17)	0.0110 (18)	−0.0115 (17)	0.0026 (14)
C7	0.070 (2)	0.0462 (16)	0.0448 (17)	0.0078 (15)	−0.0052 (14)	0.0015 (13)
C8	0.0501 (16)	0.0346 (13)	0.0419 (15)	−0.0011 (12)	−0.0037 (12)	0.0025 (11)
C9	0.0481 (16)	0.0368 (14)	0.0505 (16)	−0.0013 (12)	−0.0068 (13)	0.0021 (12)
C10	0.0368 (15)	0.0425 (14)	0.0464 (16)	−0.0034 (12)	0.0067 (12)	−0.0055 (12)
C11	0.0665 (19)	0.0400 (15)	0.0479 (17)	0.0057 (14)	0.0020 (15)	−0.0024 (13)
C12	0.077 (2)	0.0564 (17)	0.0457 (17)	0.0053 (16)	−0.0019 (15)	0.0004 (14)
C13	0.065 (2)	0.081 (2)	0.0468 (18)	0.0032 (18)	0.0075 (16)	−0.0157 (16)
C14	0.058 (2)	0.091 (3)	0.065 (2)	0.0256 (19)	0.0001 (17)	−0.0299 (19)
C15	0.0466 (18)	0.074 (2)	0.0585 (19)	0.0217 (16)	−0.0017 (14)	−0.0164 (16)
C16	0.0429 (16)	0.0415 (15)	0.0472 (16)	0.0076 (12)	0.0010 (12)	−0.0031 (12)
C17	0.0383 (15)	0.0353 (14)	0.0543 (17)	0.0055 (12)	−0.0039 (13)	−0.0023 (12)
C18	0.0410 (15)	0.0341 (13)	0.0514 (17)	0.0041 (12)	−0.0020 (13)	0.0016 (12)
C19	0.0485 (17)	0.0474 (17)	0.060 (2)	0.0057 (13)	0.0024 (14)	0.0034 (14)
C20	0.069 (2)	0.069 (2)	0.056 (2)	0.0130 (18)	0.0129 (18)	0.0134 (16)
C21	0.087 (3)	0.072 (2)	0.0453 (18)	0.018 (2)	−0.0032 (18)	0.0037 (16)
C22	0.081 (2)	0.070 (2)	0.064 (2)	−0.0032 (18)	−0.0258 (19)	−0.0049 (17)
C23	0.0612 (19)	0.0512 (17)	0.059 (2)	−0.0033 (14)	−0.0071 (16)	0.0041 (14)

O1—C17	1.215 (3)	C10—C15	1.395 (3)
F1—C20	1.348 (4)	C11—C12	1.377 (4)
S1—C1	1.768 (3)	C11—H11	0.9300
S1—C16	1.784 (3)	C12—C13	1.378 (4)
Cl1—C21	1.727 (3)	C12—H12	0.9300
N1—C1	1.306 (3)	C13—C14	1.368 (4)
N1—C2	1.375 (3)	C13—H13	0.9300
C1—C8	1.434 (3)	C14—C15	1.378 (4)
C2—C3	1.359 (3)	C14—H14	0.9300
C2—C10	1.487 (3)	C15—H15	0.9300
C3—C9	1.417 (3)	C16—C17	1.508 (4)
C3—H3	0.9300	C16—H16A	0.9700
C4—C5	1.363 (4)	C16—H16B	0.9700
C4—C9	1.413 (4)	C17—C18	1.491 (4)
C4—H4	0.9300	C18—C23	1.383 (4)
C5—C6	1.392 (4)	C18—C19	1.387 (4)
C5—H5	0.9300	C19—C20	1.356 (4)
C6—C7	1.366 (4)	C19—H19	0.9300
C6—H6	0.9300	C20—C21	1.363 (5)
C7—C8	1.405 (4)	C21—C22	1.369 (5)
C7—H7	0.9300	C22—C23	1.386 (4)
C8—C9	1.410 (3)	C22—H22	0.9300
C10—C11	1.380 (4)	C23—H23	0.9300
C1—S1—C16	99.63 (12)	C13—C12—H12	120.1
C1—N1—C2	119.3 (2)	C14—C13—C12	119.3 (3)
N1—C1—C8	123.8 (2)	C14—C13—H13	120.3
N1—C1—S1	118.51 (19)	C12—C13—H13	120.3
C8—C1—S1	117.71 (19)	C13—C14—C15	120.9 (3)
C3—C2—N1	121.5 (2)	C13—C14—H14	119.5
C3—C2—C10	123.8 (2)	C15—C14—H14	119.5
N1—C2—C10	114.7 (2)	C14—C15—C10	120.6 (3)
C2—C3—C9	120.4 (2)	C14—C15—H15	119.7
C2—C3—H3	119.8	C10—C15—H15	119.7
C9—C3—H3	119.8	C17—C16—S1	114.70 (19)
C5—C4—C9	120.2 (3)	C17—C16—H16A	108.6
C5—C4—H4	119.9	S1—C16—H16A	108.6
C9—C4—H4	119.9	C17—C16—H16B	108.6
C4—C5—C6	120.9 (3)	S1—C16—H16B	108.6
C4—C5—H5	119.6	H16A—C16—H16B	107.6
C6—C5—H5	119.6	O1—C17—C18	120.0 (2)
C7—C6—C5	120.2 (3)	O1—C17—C16	121.5 (3)
C7—C6—H6	119.9	C18—C17—C16	118.6 (2)
C5—C6—H6	119.9	C23—C18—C19	119.1 (3)
C6—C7—C8	120.6 (3)	C23—C18—C17	123.3 (3)
C6—C7—H7	119.7	C19—C18—C17	117.7 (2)
C8—C7—H7	119.7	C20—C19—C18	119.7 (3)
C7—C8—C9	119.2 (2)	C20—C19—H19	120.1
C7—C8—C1	124.3 (2)	C18—C19—H19	120.1
C9—C8—C1	116.5 (2)	F1—C20—C19	119.2 (3)
C8—C9—C4	118.9 (3)	F1—C20—C21	118.8 (3)
C8—C9—C3	118.4 (2)	C19—C20—C21	122.0 (3)
C4—C9—C3	122.7 (3)	C20—C21—C22	119.0 (3)
C11—C10—C15	117.4 (2)	C20—C21—Cl1	119.7 (3)
C11—C10—C2	120.9 (2)	C22—C21—Cl1	121.2 (3)
C15—C10—C2	121.6 (2)	C21—C22—C23	120.4 (3)
C12—C11—C10	121.9 (3)	C21—C22—H22	119.8
C12—C11—H11	119.0	C23—C22—H22	119.8
C10—C11—H11	119.0	C18—C23—C22	119.8 (3)
C11—C12—C13	119.8 (3)	C18—C23—H23	120.1
C11—C12—H12	120.1	C22—C23—H23	120.1
C2—N1—C1—C8	2.0 (4)	C15—C10—C11—C12	−1.1 (4)
C2—N1—C1—S1	−177.53 (17)	C2—C10—C11—C12	−178.4 (3)
C16—S1—C1—N1	−0.8 (2)	C10—C11—C12—C13	0.2 (4)
C16—S1—C1—C8	179.56 (19)	C11—C12—C13—C14	1.2 (5)
C1—N1—C2—C3	−4.0 (4)	C12—C13—C14—C15	−1.6 (5)
C1—N1—C2—C10	175.8 (2)	C13—C14—C15—C10	0.6 (5)
N1—C2—C3—C9	3.1 (4)	C11—C10—C15—C14	0.7 (4)
C10—C2—C3—C9	−176.7 (2)	C2—C10—C15—C14	178.0 (3)
C9—C4—C5—C6	−0.5 (5)	C1—S1—C16—C17	−73.20 (19)
C4—C5—C6—C7	0.7 (5)	S1—C16—C17—O1	−19.3 (3)
C5—C6—C7—C8	−1.2 (4)	S1—C16—C17—C18	160.73 (18)
C6—C7—C8—C9	1.6 (4)	O1—C17—C18—C23	−164.7 (3)
C6—C7—C8—C1	−178.2 (3)	C16—C17—C18—C23	15.2 (4)
N1—C1—C8—C7	−179.4 (2)	O1—C17—C18—C19	16.0 (4)
S1—C1—C8—C7	0.1 (3)	C16—C17—C18—C19	−164.1 (2)
N1—C1—C8—C9	0.7 (4)	C23—C18—C19—C20	−0.6 (4)
S1—C1—C8—C9	−179.71 (18)	C17—C18—C19—C20	178.7 (2)
C7—C8—C9—C4	−1.5 (4)	C18—C19—C20—F1	−178.3 (2)
C1—C8—C9—C4	178.4 (2)	C18—C19—C20—C21	1.2 (5)
C7—C8—C9—C3	178.5 (2)	F1—C20—C21—C22	179.0 (3)
C1—C8—C9—C3	−1.6 (3)	C19—C20—C21—C22	−0.5 (5)
C5—C4—C9—C8	0.9 (4)	F1—C20—C21—Cl1	−0.8 (4)
C5—C4—C9—C3	−179.1 (3)	C19—C20—C21—Cl1	179.7 (2)
C2—C3—C9—C8	−0.2 (4)	C20—C21—C22—C23	−0.8 (5)
C2—C3—C9—C4	179.8 (3)	Cl1—C21—C22—C23	179.0 (2)
C3—C2—C10—C11	−163.1 (3)	C19—C18—C23—C22	−0.7 (4)
N1—C2—C10—C11	17.1 (3)	C17—C18—C23—C22	−180.0 (3)
C3—C2—C10—C15	19.7 (4)	C21—C22—C23—C18	1.4 (5)
N1—C2—C10—C15	−160.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···S1	0.93	2.68	3.076 (3)	107
C11—H11···N1	0.93	2.47	2.795 (4)	101