2-[4-tert-Butyl-5-(2-chloro-benz-yl)-1,3-thia-zol-2-yl]isoindoline-1,3-dione.

In the title compound, C(22)H(19)ClN(2)O(2)S, the dihedral angle between the phenyl-ene ring and the phthalimide ring system is 4.4 (1)°. There is no hydrogen bonding or π-π stacking in the crystal structure.

Related literature

For background to thia­zole derivatives, see: Kazzouli et al. (2002 ▶); Holla et al. (2003 ▶); Hu et al. (2008 ▶), For background to phthalimide derivatives, see: Lima et al. (2002 ▶); Miyachi et al. (1997 ▶); Yachide et al. (2007 ▶).

Experimental

Crystal data

C22H19ClN2O2S

M = 410.90

Triclinic,

a = 7.8357 (4) Å

b = 8.1587 (4) Å

c = 16.1487 (8) Å

α = 100.404 (1)°

β = 95.897 (1)°

γ = 96.490 (1)°

V = 1000.85 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.32 mm−1

T = 173 K

0.46 × 0.30 × 0.28 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.868, T max = 0.917

7798 measured reflections

3857 independent reflections

3268 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.122

S = 1.15

3857 reflections

256 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042601/ng5049sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042601/ng5049Isup2.hkl

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

C22H19ClN2O2S	Z = 2
Mr = 410.90	F(000) = 428
Triclinic, P1	Dx = 1.363 Mg m−3
Hall symbol: -P 1	Melting point: 425 K
a = 7.8357 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1587 (4) Å	Cell parameters from 5125 reflections
c = 16.1487 (8) Å	θ = 2.6–27.0°
α = 100.404 (1)°	µ = 0.32 mm−1
β = 95.897 (1)°	T = 173 K
γ = 96.490 (1)°	Block, colorless
V = 1000.85 (9) Å3	0.46 × 0.30 × 0.28 mm

Bruker SMART 1000 CCD diffractometer	3857 independent reflections
Radiation source: fine-focus sealed tube	3268 reflections with I > 2σ(I)
graphite	Rint = 0.018
ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
Tmin = 0.868, Tmax = 0.917	k = −10→10
7798 measured reflections	l = −19→19

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0649P)2 + 0.4002P] where P = (Fo2 + 2Fc2)/3
3857 reflections	(Δ/σ)max < 0.001
256 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Experimental. The 1HNMR(CDCl3, 400 MHz) of the title compound were: 1.46(s,9H,3×CH3), 4.41 (s, 2H, CH2), 7.18~7.39 (m, 4H, C6H4), 7.79~7.96 (m, 4H, C6H4).And the yield was: 67.6%. m.p.423~427 K.

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	−0.47492 (7)	−0.21014 (8)	0.32706 (3)	0.04128 (18)
S1	0.02664 (6)	0.03724 (6)	0.16354 (3)	0.02634 (15)
C1	0.2305 (2)	0.1497 (2)	0.18229 (12)	0.0236 (4)
C2	0.1795 (3)	0.1461 (2)	0.31377 (12)	0.0266 (4)
C3	0.0266 (2)	0.0574 (2)	0.27220 (12)	0.0239 (4)
C4	0.2332 (3)	0.1918 (3)	0.40993 (13)	0.0366 (5)
C5	0.4226 (4)	0.2725 (4)	0.42868 (16)	0.0624 (9)
H5A	0.4953	0.1967	0.3993	0.094*
H5B	0.4592	0.2932	0.4900	0.094*
H5C	0.4347	0.3793	0.4088	0.094*
C6	0.2175 (3)	0.0330 (3)	0.44847 (14)	0.0389 (5)
H6A	0.0978	−0.0232	0.4360	0.058*
H6B	0.2495	0.0640	0.5101	0.058*
H6C	0.2950	−0.0434	0.4240	0.058*
C7	0.1182 (4)	0.3151 (3)	0.45113 (15)	0.0555 (7)
H7A	0.1307	0.4177	0.4275	0.083*
H7B	0.1534	0.3433	0.5126	0.083*
H7C	−0.0029	0.2630	0.4396	0.083*
C8	−0.1313 (2)	−0.0235 (2)	0.30286 (12)	0.0261 (4)
H8A	−0.2359	0.0057	0.2720	0.031*
H8B	−0.1298	0.0241	0.3639	0.031*
C9	−0.1445 (2)	−0.2135 (2)	0.29113 (12)	0.0255 (4)
C10	−0.2985 (3)	−0.3103 (3)	0.29935 (12)	0.0298 (4)
C11	−0.3166 (3)	−0.4842 (3)	0.28567 (15)	0.0422 (6)
H11	−0.4235	−0.5467	0.2909	0.051*
C12	−0.1785 (4)	−0.5656 (3)	0.26456 (18)	0.0510 (7)
H12	−0.1901	−0.6849	0.2547	0.061*
C13	−0.0231 (3)	−0.4749 (3)	0.25766 (18)	0.0492 (6)
H13	0.0730	−0.5313	0.2441	0.059*
C14	−0.0074 (3)	−0.3009 (3)	0.27052 (15)	0.0349 (5)
H14	0.1001	−0.2396	0.2651	0.042*
C15	0.4999 (2)	0.1549 (2)	0.11270 (12)	0.0248 (4)
C16	0.5493 (2)	0.2158 (2)	0.03643 (12)	0.0245 (4)
C17	0.7093 (3)	0.2341 (3)	0.00803 (14)	0.0306 (4)
H17	0.8079	0.2015	0.0369	0.037*
C18	0.7203 (3)	0.3020 (3)	−0.06437 (13)	0.0319 (5)
H18	0.8292	0.3190	−0.0847	0.038*
C19	0.5758 (3)	0.3453 (3)	−0.10749 (13)	0.0307 (4)
H19	0.5873	0.3896	−0.1574	0.037*
C20	0.4131 (2)	0.3257 (3)	−0.07953 (12)	0.0270 (4)
H20	0.3135	0.3546	−0.1094	0.032*
C21	0.4048 (2)	0.2618 (2)	−0.00597 (11)	0.0228 (4)
C22	0.2572 (2)	0.2381 (2)	0.04291 (12)	0.0249 (4)
N1	0.2936 (2)	0.2002 (2)	0.26111 (10)	0.0276 (4)
N2	0.3239 (2)	0.1807 (2)	0.11564 (10)	0.0244 (3)
O1	0.58277 (18)	0.09357 (19)	0.16259 (9)	0.0334 (3)
O2	0.10930 (18)	0.2615 (2)	0.02800 (9)	0.0374 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0275 (3)	0.0591 (4)	0.0341 (3)	−0.0019 (2)	0.0104 (2)	0.0021 (2)
S1	0.0230 (3)	0.0335 (3)	0.0218 (3)	−0.00074 (19)	0.00394 (18)	0.00557 (19)
C1	0.0242 (9)	0.0245 (9)	0.0229 (9)	0.0027 (7)	0.0047 (7)	0.0062 (7)
C2	0.0319 (10)	0.0250 (10)	0.0225 (10)	0.0002 (8)	0.0058 (8)	0.0043 (7)
C3	0.0285 (10)	0.0230 (9)	0.0224 (9)	0.0048 (7)	0.0070 (8)	0.0071 (7)
C4	0.0447 (13)	0.0408 (12)	0.0211 (10)	−0.0054 (10)	0.0049 (9)	0.0044 (9)
C5	0.0642 (18)	0.083 (2)	0.0264 (12)	−0.0353 (15)	−0.0045 (12)	0.0075 (12)
C6	0.0412 (13)	0.0510 (14)	0.0266 (11)	0.0052 (10)	0.0068 (9)	0.0125 (10)
C7	0.092 (2)	0.0431 (14)	0.0298 (12)	0.0145 (14)	0.0097 (13)	−0.0021 (10)
C8	0.0262 (10)	0.0280 (10)	0.0266 (10)	0.0047 (8)	0.0073 (8)	0.0086 (8)
C9	0.0261 (10)	0.0284 (10)	0.0225 (9)	0.0018 (8)	0.0003 (7)	0.0093 (8)
C10	0.0302 (10)	0.0370 (11)	0.0217 (9)	−0.0027 (8)	0.0026 (8)	0.0090 (8)
C11	0.0456 (13)	0.0381 (13)	0.0398 (13)	−0.0132 (10)	−0.0033 (10)	0.0154 (10)
C12	0.0573 (16)	0.0255 (11)	0.0673 (17)	−0.0004 (11)	−0.0070 (13)	0.0134 (11)
C13	0.0443 (14)	0.0326 (12)	0.0706 (18)	0.0120 (10)	−0.0009 (12)	0.0105 (12)
C14	0.0297 (11)	0.0294 (11)	0.0465 (13)	0.0037 (8)	0.0038 (9)	0.0105 (9)
C15	0.0214 (9)	0.0261 (10)	0.0266 (10)	0.0022 (7)	0.0031 (7)	0.0050 (8)
C16	0.0234 (9)	0.0258 (10)	0.0242 (9)	0.0023 (7)	0.0047 (7)	0.0044 (8)
C17	0.0198 (9)	0.0369 (11)	0.0366 (11)	0.0055 (8)	0.0064 (8)	0.0086 (9)
C18	0.0247 (10)	0.0372 (11)	0.0350 (11)	0.0021 (8)	0.0135 (9)	0.0060 (9)
C19	0.0345 (11)	0.0343 (11)	0.0227 (10)	−0.0003 (8)	0.0078 (8)	0.0045 (8)
C20	0.0244 (10)	0.0340 (11)	0.0227 (9)	0.0033 (8)	0.0019 (8)	0.0062 (8)
C21	0.0197 (9)	0.0260 (10)	0.0213 (9)	0.0006 (7)	0.0036 (7)	0.0023 (7)
C22	0.0232 (10)	0.0290 (10)	0.0227 (9)	0.0022 (7)	0.0016 (7)	0.0068 (8)
N1	0.0315 (9)	0.0268 (8)	0.0237 (8)	−0.0020 (7)	0.0060 (7)	0.0052 (7)
N2	0.0205 (8)	0.0309 (9)	0.0236 (8)	0.0034 (6)	0.0039 (6)	0.0093 (6)
O1	0.0284 (7)	0.0411 (8)	0.0343 (8)	0.0081 (6)	0.0003 (6)	0.0166 (7)
O2	0.0208 (7)	0.0607 (10)	0.0362 (8)	0.0081 (7)	0.0049 (6)	0.0216 (7)

Cl1—C10	1.741 (2)	C9—C10	1.397 (3)
S1—C1	1.7188 (19)	C10—C11	1.385 (3)
S1—C3	1.7327 (19)	C11—C12	1.373 (4)
C1—N1	1.292 (2)	C11—H11	0.9500
C1—N2	1.406 (2)	C12—C13	1.377 (4)
C2—C3	1.369 (3)	C12—H12	0.9500
C2—N1	1.385 (2)	C13—C14	1.386 (3)
C2—C4	1.532 (3)	C13—H13	0.9500
C3—C8	1.507 (3)	C14—H14	0.9500
C4—C5	1.531 (3)	C15—O1	1.197 (2)
C4—C6	1.534 (3)	C15—N2	1.422 (2)
C4—C7	1.534 (3)	C15—C16	1.480 (3)
C5—H5A	0.9800	C16—C17	1.380 (3)
C5—H5B	0.9800	C16—C21	1.386 (3)
C5—H5C	0.9800	C17—C18	1.388 (3)
C6—H6A	0.9800	C17—H17	0.9500
C6—H6B	0.9800	C18—C19	1.382 (3)
C6—H6C	0.9800	C18—H18	0.9500
C7—H7A	0.9800	C19—C20	1.398 (3)
C7—H7B	0.9800	C19—H19	0.9500
C7—H7C	0.9800	C20—C21	1.385 (3)
C8—C9	1.518 (3)	C20—H20	0.9500
C8—H8A	0.9900	C21—C22	1.480 (3)
C8—H8B	0.9900	C22—O2	1.203 (2)
C9—C14	1.391 (3)	C22—N2	1.414 (2)
C1—S1—C3	88.77 (9)	C11—C10—C9	122.3 (2)
N1—C1—N2	122.33 (17)	C11—C10—Cl1	118.45 (17)
N1—C1—S1	115.89 (14)	C9—C10—Cl1	119.27 (16)
N2—C1—S1	121.76 (14)	C12—C11—C10	119.4 (2)
C3—C2—N1	114.54 (17)	C12—C11—H11	120.3
C3—C2—C4	127.00 (18)	C10—C11—H11	120.3
N1—C2—C4	118.45 (17)	C11—C12—C13	120.3 (2)
C2—C3—C8	132.65 (17)	C11—C12—H12	119.9
C2—C3—S1	109.93 (14)	C13—C12—H12	119.9
C8—C3—S1	117.41 (14)	C12—C13—C14	119.8 (2)
C5—C4—C2	109.70 (17)	C12—C13—H13	120.1
C5—C4—C6	107.7 (2)	C14—C13—H13	120.1
C2—C4—C6	110.24 (18)	C13—C14—C9	121.9 (2)
C5—C4—C7	109.5 (2)	C13—C14—H14	119.1
C2—C4—C7	110.09 (19)	C9—C14—H14	119.1
C6—C4—C7	109.56 (19)	O1—C15—N2	124.78 (18)
C4—C5—H5A	109.5	O1—C15—C16	129.95 (18)
C4—C5—H5B	109.5	N2—C15—C16	105.26 (15)
H5A—C5—H5B	109.5	C17—C16—C21	121.50 (18)
C4—C5—H5C	109.5	C17—C16—C15	129.50 (18)
H5A—C5—H5C	109.5	C21—C16—C15	108.97 (16)
H5B—C5—H5C	109.5	C16—C17—C18	117.32 (18)
C4—C6—H6A	109.5	C16—C17—H17	121.3
C4—C6—H6B	109.5	C18—C17—H17	121.3
H6A—C6—H6B	109.5	C19—C18—C17	121.24 (18)
C4—C6—H6C	109.5	C19—C18—H18	119.4
H6A—C6—H6C	109.5	C17—C18—H18	119.4
H6B—C6—H6C	109.5	C18—C19—C20	121.71 (19)
C4—C7—H7A	109.5	C18—C19—H19	119.1
C4—C7—H7B	109.5	C20—C19—H19	119.1
H7A—C7—H7B	109.5	C21—C20—C19	116.44 (18)
C4—C7—H7C	109.5	C21—C20—H20	121.8
H7A—C7—H7C	109.5	C19—C20—H20	121.8
H7B—C7—H7C	109.5	C20—C21—C16	121.75 (17)
C3—C8—C9	113.97 (16)	C20—C21—C22	129.59 (17)
C3—C8—H8A	108.8	C16—C21—C22	108.59 (16)
C9—C8—H8A	108.8	O2—C22—N2	124.31 (18)
C3—C8—H8B	108.8	O2—C22—C21	129.93 (18)
C9—C8—H8B	108.8	N2—C22—C21	105.75 (15)
H8A—C8—H8B	107.7	C1—N1—C2	110.85 (16)
C14—C9—C10	116.45 (19)	C1—N2—C22	125.37 (16)
C14—C9—C8	122.59 (17)	C1—N2—C15	123.47 (15)
C10—C9—C8	120.96 (18)	C22—N2—C15	111.15 (15)
C3—S1—C1—N1	−0.76 (16)	N2—C15—C16—C21	−4.5 (2)
C3—S1—C1—N2	177.63 (16)	C21—C16—C17—C18	0.6 (3)
N1—C2—C3—C8	−179.96 (18)	C15—C16—C17—C18	−177.14 (19)
C4—C2—C3—C8	−0.9 (4)	C16—C17—C18—C19	−1.7 (3)
N1—C2—C3—S1	1.1 (2)	C17—C18—C19—C20	1.1 (3)
C4—C2—C3—S1	−179.79 (17)	C18—C19—C20—C21	0.5 (3)
C1—S1—C3—C2	−0.25 (15)	C19—C20—C21—C16	−1.6 (3)
C1—S1—C3—C8	−179.33 (15)	C19—C20—C21—C22	175.01 (18)
C3—C2—C4—C5	173.1 (2)	C17—C16—C21—C20	1.1 (3)
N1—C2—C4—C5	−7.9 (3)	C15—C16—C21—C20	179.23 (17)
C3—C2—C4—C6	54.6 (3)	C17—C16—C21—C22	−176.19 (18)
N1—C2—C4—C6	−126.4 (2)	C15—C16—C21—C22	2.0 (2)
C3—C2—C4—C7	−66.4 (3)	C20—C21—C22—O2	3.8 (4)
N1—C2—C4—C7	112.6 (2)	C16—C21—C22—O2	−179.2 (2)
C2—C3—C8—C9	−104.1 (2)	C20—C21—C22—N2	−175.65 (19)
S1—C3—C8—C9	74.74 (19)	C16—C21—C22—N2	1.3 (2)
C3—C8—C9—C14	12.5 (3)	N2—C1—N1—C2	−176.86 (17)
C3—C8—C9—C10	−166.43 (18)	S1—C1—N1—C2	1.5 (2)
C14—C9—C10—C11	−1.7 (3)	C3—C2—N1—C1	−1.7 (2)
C8—C9—C10—C11	177.34 (19)	C4—C2—N1—C1	179.14 (18)
C14—C9—C10—Cl1	178.77 (15)	N1—C1—N2—C22	−134.9 (2)
C8—C9—C10—Cl1	−2.2 (3)	S1—C1—N2—C22	46.8 (2)
C9—C10—C11—C12	1.0 (3)	N1—C1—N2—C15	46.1 (3)
Cl1—C10—C11—C12	−179.38 (19)	S1—C1—N2—C15	−132.20 (17)
C10—C11—C12—C13	0.5 (4)	O2—C22—N2—C1	−2.9 (3)
C11—C12—C13—C14	−1.2 (4)	C21—C22—N2—C1	176.62 (16)
C12—C13—C14—C9	0.6 (4)	O2—C22—N2—C15	176.22 (19)
C10—C9—C14—C13	0.8 (3)	C21—C22—N2—C15	−4.3 (2)
C8—C9—C14—C13	−178.1 (2)	O1—C15—N2—C1	5.6 (3)
O1—C15—C16—C17	−7.7 (4)	C16—C15—N2—C1	−175.46 (16)
N2—C15—C16—C17	173.5 (2)	O1—C15—N2—C22	−173.47 (19)
O1—C15—C16—C21	174.3 (2)	C16—C15—N2—C22	5.4 (2)