7-Chloro-4-(2,5-dichloro-phen-yl)-1-phenyl-1H-thio-chromeno[2,3-b]pyridine-2,5(3H,4H)-dione.

In the crystal structure of the title compound, C(24)H(14)Cl(3)NO(2)S, the tetra-hydro-pyridine ring adopts a half-chair conformation and both pendant benzene rings are oriented nearly perpendicular to the thio-chromeno[2,3-b]pyridine system.

Related literature

For related literature, see: Ingall et al. (1996 ▶), Wang et al. (2006 ▶); Quaglia et al. (2002 ▶).

Experimental

Crystal data

C24H14Cl3NO2S

M = 486.77

Monoclinic,

a = 13.624 (5) Å

b = 13.474 (5) Å

c = 11.861 (4) Å

β = 95.042 (6)°

V = 2168.9 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.54 mm−1

T = 294 (2) K

0.18 × 0.12 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.909, T max = 0.948

12228 measured reflections

4426 independent reflections

2650 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.112

S = 0.99

4426 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 1999 ▶); 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 global, I. DOI: 10.1107/S1600536808000573/nc2085sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000573/nc2085Isup2.hkl

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

C24H14Cl3NO2S	F000 = 992
Mr = 486.77	Dx = 1.491 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2857 reflections
a = 13.624 (5) Å	θ = 2.3–23.4º
b = 13.474 (5) Å	µ = 0.54 mm−1
c = 11.861 (4) Å	T = 294 (2) K
β = 95.042 (6)º	Prism, yellow
V = 2168.9 (14) Å3	0.18 × 0.12 × 0.10 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	4426 independent reflections
Radiation source: fine-focus sealed tube	2650 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.049
T = 294(2) K	θmax = 26.5º
φ and ω scans	θmin = 1050º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −16→17
Tmin = 0.909, Tmax = 0.948	k = −13→16
12228 measured reflections	l = −14→14

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0479P)2 + 0.2323P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.043	(Δ/σ)max = 0.001
wR(F2) = 0.112	Δρmax = 0.28 e Å−3
S = 0.99	Δρmin = −0.26 e Å−3
4426 reflections	Extinction correction: none
280 parameters

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
S1	0.90221 (5)	0.18709 (5)	0.44648 (6)	0.04544 (19)
Cl1	1.15911 (7)	0.38600 (6)	0.09743 (8)	0.0852 (3)
Cl2	0.73863 (7)	0.67908 (6)	0.56211 (8)	0.0848 (3)
Cl3	0.48232 (6)	0.37484 (7)	0.27266 (7)	0.0859 (3)
O1	0.92297 (13)	0.51190 (12)	0.38778 (15)	0.0534 (5)
O2	0.66915 (15)	0.28572 (14)	0.71540 (16)	0.0633 (6)
N1	0.76934 (14)	0.25141 (14)	0.57736 (16)	0.0395 (5)
C1	0.97544 (16)	0.24922 (17)	0.3549 (2)	0.0388 (6)
C2	1.03240 (18)	0.18948 (19)	0.2898 (2)	0.0505 (7)
H2	1.0327	0.1211	0.3004	0.061*
C3	1.0880 (2)	0.2301 (2)	0.2103 (2)	0.0581 (8)
H3	1.1246	0.1896	0.1663	0.070*
C4	1.08877 (19)	0.3324 (2)	0.1967 (2)	0.0524 (7)
C5	1.03478 (18)	0.39236 (19)	0.2611 (2)	0.0464 (6)
H5	1.0366	0.4608	0.2511	0.056*
C6	0.97697 (16)	0.35243 (17)	0.3415 (2)	0.0370 (6)
C7	0.91855 (17)	0.42134 (18)	0.4054 (2)	0.0387 (6)
C8	0.85216 (17)	0.38283 (17)	0.4844 (2)	0.0362 (6)
C9	0.79469 (17)	0.45849 (17)	0.5447 (2)	0.0408 (6)
H9	0.8373	0.5166	0.5583	0.049*
C10	0.77372 (19)	0.41789 (18)	0.6606 (2)	0.0470 (7)
H10A	0.8346	0.4175	0.7097	0.056*
H10B	0.7281	0.4621	0.6940	0.056*
C11	0.73121 (19)	0.31487 (19)	0.6559 (2)	0.0450 (6)
C12	0.83881 (16)	0.28430 (17)	0.50370 (19)	0.0357 (6)
C13	0.73107 (17)	0.15033 (17)	0.56871 (19)	0.0365 (6)
C14	0.7620 (2)	0.0818 (2)	0.6502 (2)	0.0540 (7)
H14	0.8082	0.0993	0.7093	0.065*
C15	0.7234 (2)	−0.0139 (2)	0.6432 (3)	0.0646 (8)
H15	0.7440	−0.0608	0.6978	0.077*
C16	0.6561 (2)	−0.0390 (2)	0.5570 (3)	0.0654 (9)
H16	0.6301	−0.1029	0.5528	0.079*
C17	0.6263 (2)	0.0299 (2)	0.4760 (3)	0.0656 (9)
H17	0.5806	0.0121	0.4167	0.079*
C18	0.6631 (2)	0.1252 (2)	0.4812 (2)	0.0533 (7)
H18	0.6422	0.1716	0.4263	0.064*
C19	0.70135 (18)	0.49370 (19)	0.4760 (2)	0.0430 (6)
C20	0.6704 (2)	0.5922 (2)	0.4790 (2)	0.0545 (7)
C21	0.5847 (3)	0.6240 (2)	0.4178 (3)	0.0715 (9)
H21	0.5663	0.6904	0.4204	0.086*
C22	0.5269 (2)	0.5584 (3)	0.3538 (3)	0.0687 (9)
H22	0.4692	0.5796	0.3132	0.082*
C23	0.55580 (19)	0.4603 (2)	0.3506 (2)	0.0548 (7)
C24	0.64242 (18)	0.4289 (2)	0.4096 (2)	0.0480 (7)
H24	0.6614	0.3629	0.4045	0.058*

	U11	U22	U33	U12	U13	U23
S1	0.0490 (4)	0.0304 (3)	0.0585 (4)	−0.0002 (3)	0.0140 (3)	0.0006 (3)
Cl1	0.0958 (6)	0.0721 (6)	0.0966 (6)	−0.0206 (5)	0.0581 (5)	−0.0068 (5)
Cl2	0.0883 (6)	0.0413 (4)	0.1249 (8)	0.0078 (4)	0.0104 (6)	−0.0151 (5)
Cl3	0.0627 (5)	0.1131 (8)	0.0772 (6)	0.0090 (5)	−0.0198 (4)	−0.0077 (5)
O1	0.0648 (12)	0.0295 (10)	0.0678 (12)	0.0001 (8)	0.0161 (10)	0.0042 (9)
O2	0.0759 (14)	0.0576 (13)	0.0610 (12)	−0.0091 (10)	0.0315 (11)	−0.0065 (10)
N1	0.0441 (12)	0.0354 (11)	0.0394 (11)	−0.0040 (10)	0.0067 (10)	−0.0026 (9)
C1	0.0323 (13)	0.0371 (14)	0.0466 (15)	−0.0055 (11)	0.0021 (11)	−0.0025 (12)
C2	0.0500 (16)	0.0335 (14)	0.0698 (18)	−0.0063 (12)	0.0161 (14)	−0.0092 (14)
C3	0.0531 (17)	0.0519 (18)	0.073 (2)	−0.0066 (14)	0.0274 (15)	−0.0147 (15)
C4	0.0494 (17)	0.0490 (17)	0.0612 (18)	−0.0118 (13)	0.0181 (14)	−0.0051 (14)
C5	0.0436 (15)	0.0381 (14)	0.0581 (16)	−0.0082 (12)	0.0075 (13)	0.0000 (13)
C6	0.0302 (13)	0.0336 (13)	0.0465 (14)	−0.0036 (11)	−0.0005 (11)	−0.0006 (12)
C7	0.0369 (14)	0.0339 (14)	0.0444 (15)	−0.0034 (11)	−0.0022 (12)	−0.0012 (12)
C8	0.0353 (13)	0.0316 (13)	0.0408 (14)	0.0005 (11)	−0.0017 (11)	−0.0026 (11)
C9	0.0417 (14)	0.0347 (14)	0.0457 (15)	−0.0015 (11)	0.0024 (12)	−0.0029 (12)
C10	0.0558 (16)	0.0411 (15)	0.0438 (15)	−0.0003 (13)	0.0022 (13)	−0.0073 (12)
C11	0.0522 (16)	0.0462 (16)	0.0355 (14)	0.0019 (13)	−0.0014 (13)	−0.0021 (13)
C12	0.0336 (13)	0.0368 (13)	0.0360 (13)	−0.0020 (11)	−0.0004 (11)	−0.0014 (11)
C13	0.0360 (13)	0.0373 (13)	0.0372 (14)	−0.0044 (11)	0.0083 (11)	−0.0002 (11)
C14	0.0525 (17)	0.0521 (17)	0.0558 (17)	−0.0012 (14)	−0.0050 (14)	0.0090 (15)
C15	0.072 (2)	0.0414 (17)	0.082 (2)	0.0038 (15)	0.0182 (19)	0.0161 (16)
C16	0.069 (2)	0.0457 (18)	0.087 (2)	−0.0152 (16)	0.0352 (19)	−0.0166 (18)
C17	0.066 (2)	0.070 (2)	0.061 (2)	−0.0267 (17)	0.0071 (16)	−0.0144 (18)
C18	0.0604 (18)	0.0563 (18)	0.0424 (16)	−0.0108 (15)	−0.0004 (14)	0.0055 (14)
C19	0.0424 (15)	0.0423 (15)	0.0458 (15)	0.0057 (12)	0.0120 (13)	0.0036 (13)
C20	0.0566 (18)	0.0454 (16)	0.0632 (18)	0.0124 (14)	0.0155 (15)	0.0031 (14)
C21	0.079 (2)	0.057 (2)	0.081 (2)	0.0328 (18)	0.019 (2)	0.0087 (18)
C22	0.058 (2)	0.088 (3)	0.061 (2)	0.0302 (19)	0.0091 (16)	0.0115 (19)
C23	0.0449 (16)	0.073 (2)	0.0468 (16)	0.0085 (15)	0.0052 (13)	0.0046 (15)
C24	0.0444 (16)	0.0506 (16)	0.0495 (16)	0.0099 (13)	0.0063 (13)	0.0027 (14)

S1—C12	1.739 (2)	C9—H9	0.9800
S1—C1	1.751 (2)	C10—C11	1.503 (3)
Cl1—C4	1.739 (3)	C10—H10A	0.9700
Cl2—C20	1.744 (3)	C10—H10B	0.9700
Cl3—C23	1.737 (3)	C13—C18	1.371 (3)
O1—C7	1.240 (3)	C13—C14	1.376 (3)
O2—C11	1.213 (3)	C14—C15	1.393 (4)
N1—C11	1.398 (3)	C14—H14	0.9300
N1—C12	1.414 (3)	C15—C16	1.355 (4)
N1—C13	1.459 (3)	C15—H15	0.9300
C1—C2	1.397 (3)	C16—C17	1.372 (4)
C1—C6	1.400 (3)	C16—H16	0.9300
C2—C3	1.374 (3)	C17—C18	1.377 (4)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.389 (4)	C18—H18	0.9300
C3—H3	0.9300	C19—C24	1.384 (3)
C4—C5	1.370 (3)	C19—C20	1.395 (3)
C5—C6	1.397 (3)	C20—C21	1.387 (4)
C5—H5	0.9300	C21—C22	1.368 (4)
C6—C7	1.475 (3)	C21—H21	0.9300
C7—C8	1.454 (3)	C22—C23	1.382 (4)
C8—C12	1.362 (3)	C22—H22	0.9300
C8—C9	1.504 (3)	C23—C24	1.384 (3)
C9—C19	1.525 (3)	C24—H24	0.9300
C9—C10	1.530 (3)
C12—S1—C1	102.22 (11)	O2—C11—C10	124.3 (2)
C11—N1—C12	121.9 (2)	N1—C11—C10	115.2 (2)
C11—N1—C13	117.80 (19)	C8—C12—N1	121.0 (2)
C12—N1—C13	120.23 (19)	C8—C12—S1	126.18 (19)
C2—C1—C6	119.7 (2)	N1—C12—S1	112.79 (16)
C2—C1—S1	116.23 (18)	C18—C13—C14	120.7 (2)
C6—C1—S1	124.06 (19)	C18—C13—N1	119.8 (2)
C3—C2—C1	121.1 (2)	C14—C13—N1	119.4 (2)
C3—C2—H2	119.4	C13—C14—C15	119.2 (3)
C1—C2—H2	119.4	C13—C14—H14	120.4
C2—C3—C4	119.0 (3)	C15—C14—H14	120.4
C2—C3—H3	120.5	C16—C15—C14	120.2 (3)
C4—C3—H3	120.5	C16—C15—H15	119.9
C5—C4—C3	120.7 (2)	C14—C15—H15	119.9
C5—C4—Cl1	119.2 (2)	C15—C16—C17	119.8 (3)
C3—C4—Cl1	120.1 (2)	C15—C16—H16	120.1
C4—C5—C6	121.1 (2)	C17—C16—H16	120.1
C4—C5—H5	119.5	C16—C17—C18	121.1 (3)
C6—C5—H5	119.4	C16—C17—H17	119.5
C5—C6—C1	118.3 (2)	C18—C17—H17	119.5
C5—C6—C7	118.1 (2)	C13—C18—C17	118.9 (3)
C1—C6—C7	123.6 (2)	C13—C18—H18	120.6
O1—C7—C8	120.1 (2)	C17—C18—H18	120.6
O1—C7—C6	119.8 (2)	C24—C19—C20	117.0 (2)
C8—C7—C6	120.0 (2)	C24—C19—C9	121.5 (2)
C12—C8—C7	123.8 (2)	C20—C19—C9	121.5 (2)
C12—C8—C9	119.9 (2)	C21—C20—C19	121.5 (3)
C7—C8—C9	116.4 (2)	C21—C20—Cl2	118.1 (2)
C8—C9—C19	113.64 (19)	C19—C20—Cl2	120.4 (2)
C8—C9—C10	109.34 (19)	C22—C21—C20	120.5 (3)
C19—C9—C10	112.3 (2)	C22—C21—H21	119.8
C8—C9—H9	107.1	C20—C21—H21	119.8
C19—C9—H9	107.1	C21—C22—C23	118.9 (3)
C10—C9—H9	107.1	C21—C22—H22	120.6
C11—C10—C9	113.5 (2)	C23—C22—H22	120.6
C11—C10—H10A	108.9	C22—C23—C24	120.7 (3)
C9—C10—H10A	108.9	C22—C23—Cl3	119.8 (2)
C11—C10—H10B	108.9	C24—C23—Cl3	119.5 (2)
C9—C10—H10B	108.9	C23—C24—C19	121.4 (3)
H10A—C10—H10B	107.7	C23—C24—H24	119.3
O2—C11—N1	120.6 (2)	C19—C24—H24	119.3
C12—S1—C1—C2	−176.43 (19)	C7—C8—C12—S1	4.3 (3)
C12—S1—C1—C6	1.4 (2)	C9—C8—C12—S1	−177.11 (17)
C6—C1—C2—C3	−1.8 (4)	C11—N1—C12—C8	−17.6 (3)
S1—C1—C2—C3	176.1 (2)	C13—N1—C12—C8	158.9 (2)
C1—C2—C3—C4	1.3 (4)	C11—N1—C12—S1	161.51 (17)
C2—C3—C4—C5	−0.2 (4)	C13—N1—C12—S1	−22.0 (3)
C2—C3—C4—Cl1	179.6 (2)	C1—S1—C12—C8	−4.3 (2)
C3—C4—C5—C6	−0.5 (4)	C1—S1—C12—N1	176.67 (16)
Cl1—C4—C5—C6	179.76 (19)	C11—N1—C13—C18	101.9 (3)
C4—C5—C6—C1	0.0 (4)	C12—N1—C13—C18	−74.8 (3)
C4—C5—C6—C7	−178.2 (2)	C11—N1—C13—C14	−76.6 (3)
C2—C1—C6—C5	1.1 (3)	C12—N1—C13—C14	106.7 (3)
S1—C1—C6—C5	−176.60 (18)	C18—C13—C14—C15	−0.1 (4)
C2—C1—C6—C7	179.3 (2)	N1—C13—C14—C15	178.4 (2)
S1—C1—C6—C7	1.5 (3)	C13—C14—C15—C16	−0.1 (4)
C5—C6—C7—O1	−1.0 (3)	C14—C15—C16—C17	0.5 (4)
C1—C6—C7—O1	−179.1 (2)	C15—C16—C17—C18	−0.7 (4)
C5—C6—C7—C8	175.8 (2)	C14—C13—C18—C17	−0.1 (4)
C1—C6—C7—C8	−2.3 (3)	N1—C13—C18—C17	−178.6 (2)
O1—C7—C8—C12	176.1 (2)	C16—C17—C18—C13	0.5 (4)
C6—C7—C8—C12	−0.7 (3)	C8—C9—C19—C24	38.9 (3)
O1—C7—C8—C9	−2.5 (3)	C10—C9—C19—C24	−85.8 (3)
C6—C7—C8—C9	−179.3 (2)	C8—C9—C19—C20	−142.5 (2)
C12—C8—C9—C19	−95.5 (3)	C10—C9—C19—C20	92.8 (3)
C7—C8—C9—C19	83.2 (3)	C24—C19—C20—C21	−0.3 (4)
C12—C8—C9—C10	30.8 (3)	C9—C19—C20—C21	−179.0 (2)
C7—C8—C9—C10	−150.5 (2)	C24—C19—C20—Cl2	178.93 (19)
C8—C9—C10—C11	−49.6 (3)	C9—C19—C20—Cl2	0.3 (3)
C19—C9—C10—C11	77.5 (3)	C19—C20—C21—C22	1.1 (4)
C12—N1—C11—O2	177.4 (2)	Cl2—C20—C21—C22	−178.2 (2)
C13—N1—C11—O2	0.8 (3)	C20—C21—C22—C23	−0.5 (5)
C12—N1—C11—C10	−3.4 (3)	C21—C22—C23—C24	−1.0 (4)
C13—N1—C11—C10	180.0 (2)	C21—C22—C23—Cl3	178.5 (2)
C9—C10—C11—O2	−143.4 (3)	C22—C23—C24—C19	1.8 (4)
C9—C10—C11—N1	37.4 (3)	Cl3—C23—C24—C19	−177.65 (19)
C7—C8—C12—N1	−176.7 (2)	C20—C19—C24—C23	−1.1 (4)
C9—C8—C12—N1	1.9 (3)	C9—C19—C24—C23	177.5 (2)