8-(4-Chloro­phen­oxy)-7-(4-chloro­phen­yl)-1,2,5-trimethylthieno[2′,3′;2,3]pyrido[4,5-d]pyrimidin-6(7H)-one

Liu, J.-C.; Peng, H.; Meng, X.-G.; Ding, M.-W.; He, H.-W.

doi:10.1107/S1600536805028783

8-(4-Chlorophenoxy)-7-(4-chlorophenyl)-1,2,5-trimethylthieno[2',3';2,3]pyrido[4,5-d]pyrimidin-6(7H)-one

J.-C. Liu, H. Peng, X.-G. Meng, M.-W. Ding and H.-W. He

In the molecule of the title compound, C₂₄H₁₇Cl₂N₃O₂S, the mean plane of the tricyclic thienopyridopyrimidine system is roughly orthogonal to both benzene planes, the dihedral angles being 107.8 (1) and 99.6 (1)° for the benzene planes in the p-chlorophenoxy and p-chlorophenyl groups, respectively. The dihedral angle formed by the two benzene rings is 101.4 (1)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028783/ya6254sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028783/ya6254Isup2.hkl Contains datablock I

CCDC reference: 264861

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.003 Å
R factor = 0.050
wR factor = 0.158
Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.416
            Value of mu given      =     0.420
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The derivatives of heterocyclic systems involving pyridine rings attract considerable interest because of their remarkable biological properties. Many pyridopyrimidines show biological activity and exhibit germicidal effect (Anderson & Broom, 1977). According to recent studies of Zheng et al. (2001), pyrimidine derivatives make up a novel class of adenosine kinase inhibitors. A large number of general methods for the preparation of pyridopyrimidine derivatives have been reported within the past few years (Rewcastle et al., 1996; Maruoka et al., 2004). Recently, we have developed a new and facile regioselective annulation process, which proceeds smoothly under mild conditions via a tandem aza–Wittig and cyclization reaction, and produces novel 2-substituted 5,8,9-trimethyl-3-phenyl-thieno[3',2';5,6] pyrido[4,3-d]pyrimidine-4(3H)-ones. In this paper, the crystal structure of the title compound, (I), is reported.

The molecular structure of (I) is shown in Fig. 1. Selected bond lengths and angles are listed in Table 1. In the molecule of the title compound, the mean plane of the tricyclic thienopyridopyrimidine 13-membered ring system S1/C2/C3/C5/C10/C9/C7/N1/C6/C12/N3/C11/N2 is roughly orthogonal to both benzene planes. The dihedral angles between the mean plane of the tricylic system and the benzene planes C13–C18 and C19–C24 are 99.6 (1)° and 107.8 (1)°, respectively; the benzene rings form a dihedral angle of 101.4 (1)° with each other.

Experimental top

The title compound was prepared according to the literature procedure (Zhou et al., 2005). Suitable crystals were obtained by evaporation of a methanol solution (m.p. > 573 K). Analysis calculated for C₂₄H₁₇Cl₂N₃O₂S: C, 59.75; H, 3.53; N, 8.71. Found: C, 60.11; H, 3.66; N, 8.52.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. View of the molecule of (I), showing the atom-numbering scheme and 50% probability displacement ellipsoids.

(I) top

Crystal data top

C₂₄H₁₇Cl₂N₃O₂S	F(000) = 992
M_r = 482.37	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3451 reflections
a = 11.1861 (17) Å	θ = 2.3–24.4°
b = 10.3346 (16) Å	µ = 0.42 mm⁻¹
c = 19.517 (3) Å	T = 292 K
β = 101.377 (3)°	Block, colorless
V = 2212.0 (6) Å³	0.35 × 0.30 × 0.30 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4799 independent reflections
Radiation source: fine-focus sealed tube	3590 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −14→14
T_min = 0.868, T_max = 0.885	k = −13→10
12672 measured reflections	l = −20→24

Refinement top

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0852P)² + 0.2736P] where P = (F_o² + 2F_c²)/3
4799 reflections	(Δ/σ)_max = 0.001
292 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₄H₁₇Cl₂N₃O₂S	V = 2212.0 (6) Å³
M_r = 482.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.1861 (17) Å	µ = 0.42 mm⁻¹
b = 10.3346 (16) Å	T = 292 K
c = 19.517 (3) Å	0.35 × 0.30 × 0.30 mm
β = 101.377 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4799 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	3590 reflections with I > 2σ(I)
T_min = 0.868, T_max = 0.885	R_int = 0.026
12672 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.10	Δρ_max = 0.39 e Å⁻³
4799 reflections	Δρ_min = −0.32 e Å⁻³
292 parameters

Special details top

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
C1	0.6223 (3)	0.5442 (3)	1.24519 (13)	0.0696 (8)
H1A	0.6629	0.4752	1.2735	0.104*
H1B	0.5662	0.5862	1.2694	0.104*
H1C	0.6815	0.6058	1.2361	0.104*
C2	0.5531 (2)	0.4897 (2)	1.17653 (12)	0.0490 (6)
C3	0.5958 (2)	0.4087 (2)	1.13215 (11)	0.0426 (5)
C4	0.7225 (2)	0.3544 (3)	1.14545 (14)	0.0565 (6)
H4A	0.7672	0.3866	1.1892	0.085*
H4B	0.7628	0.3802	1.1085	0.085*
H4C	0.7188	0.2617	1.1471	0.085*
C5	0.5015 (2)	0.3787 (2)	1.07222 (11)	0.0400 (5)
C6	0.3898 (2)	0.4383 (2)	1.07398 (12)	0.0446 (5)
C7	0.2878 (2)	0.3578 (2)	0.97087 (13)	0.0473 (5)
C8	0.1710 (2)	0.3519 (3)	0.91922 (15)	0.0599 (7)
H8A	0.1358	0.2674	0.9202	0.090*
H8B	0.1861	0.3688	0.8733	0.090*
H8C	0.1158	0.4157	0.9307	0.090*
C9	0.3954 (2)	0.2900 (2)	0.96231 (11)	0.0407 (5)
C10	0.5023 (2)	0.3012 (2)	1.01258 (11)	0.0388 (5)
C11	0.6097 (2)	0.1733 (2)	0.95264 (12)	0.0442 (5)
C12	0.3966 (2)	0.2079 (2)	0.90069 (12)	0.0460 (5)
C13	0.5248 (2)	0.0682 (2)	0.84140 (11)	0.0428 (5)
C14	0.4879 (3)	−0.0578 (2)	0.84141 (13)	0.0577 (7)
H14	0.4469	−0.0872	0.8755	0.069*
C15	0.5120 (3)	−0.1415 (3)	0.79058 (15)	0.0631 (7)
H15	0.4881	−0.2277	0.7905	0.076*
C16	0.5711 (2)	−0.0968 (2)	0.74050 (12)	0.0465 (5)
C17	0.6044 (3)	0.0303 (2)	0.73848 (13)	0.0550 (6)
H17	0.6418	0.0604	0.7030	0.066*
C18	0.5816 (2)	0.1134 (2)	0.78996 (13)	0.0528 (6)
H18	0.6048	0.1997	0.7897	0.063*
C19	0.8159 (2)	0.1282 (2)	0.99461 (12)	0.0479 (6)
C20	0.8538 (2)	0.0232 (3)	1.03616 (13)	0.0567 (6)
H20	0.8077	−0.0523	1.0319	0.068*
C21	0.9608 (3)	0.0315 (3)	1.08404 (14)	0.0643 (8)
H21	0.9884	−0.0391	1.1123	0.077*
C22	1.0274 (2)	0.1440 (3)	1.09037 (13)	0.0601 (7)
C23	0.9880 (2)	0.2500 (3)	1.04856 (14)	0.0594 (7)
H23	1.0336	0.3258	1.0530	0.071*
C24	0.8811 (2)	0.2418 (3)	1.00080 (13)	0.0530 (6)
H24	0.8528	0.3124	0.9727	0.064*
Cl1	0.61203 (6)	−0.20541 (7)	0.68093 (4)	0.0681 (2)
Cl2	1.16368 (9)	0.15234 (12)	1.14971 (5)	0.1082 (4)
N1	0.28660 (18)	0.4309 (2)	1.02700 (11)	0.0504 (5)
N2	0.61000 (16)	0.24066 (19)	1.00748 (9)	0.0429 (4)
N3	0.51221 (17)	0.15207 (18)	0.89949 (10)	0.0438 (4)
O1	0.31296 (16)	0.1841 (2)	0.85372 (10)	0.0664 (5)
O2	0.71109 (15)	0.11379 (18)	0.94171 (8)	0.0582 (5)
S1	0.40067 (6)	0.52986 (6)	1.14956 (3)	0.0567 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.090 (2)	0.0714 (19)	0.0459 (14)	0.0061 (16)	0.0100 (14)	−0.0134 (13)
C2	0.0628 (15)	0.0424 (12)	0.0423 (12)	−0.0004 (11)	0.0117 (11)	0.0012 (10)
C3	0.0493 (13)	0.0402 (12)	0.0380 (11)	−0.0002 (10)	0.0076 (10)	0.0017 (9)
C4	0.0512 (14)	0.0631 (16)	0.0521 (14)	−0.0004 (12)	0.0030 (12)	−0.0070 (12)
C5	0.0438 (12)	0.0360 (11)	0.0411 (11)	0.0009 (9)	0.0109 (9)	0.0038 (9)
C6	0.0500 (13)	0.0382 (12)	0.0485 (13)	0.0026 (10)	0.0170 (11)	0.0021 (10)
C7	0.0402 (12)	0.0444 (13)	0.0573 (14)	0.0001 (10)	0.0099 (11)	0.0084 (11)
C8	0.0406 (13)	0.0617 (16)	0.0732 (17)	0.0042 (11)	0.0008 (12)	0.0017 (13)
C9	0.0385 (11)	0.0400 (12)	0.0431 (12)	−0.0021 (9)	0.0067 (9)	0.0016 (9)
C10	0.0407 (11)	0.0361 (11)	0.0397 (11)	−0.0018 (9)	0.0081 (9)	0.0019 (9)
C11	0.0410 (12)	0.0494 (13)	0.0406 (12)	0.0033 (10)	0.0043 (10)	−0.0026 (10)
C12	0.0435 (13)	0.0456 (13)	0.0468 (13)	−0.0041 (10)	0.0039 (11)	0.0001 (10)
C13	0.0446 (12)	0.0441 (12)	0.0373 (11)	−0.0010 (10)	0.0019 (9)	−0.0039 (9)
C14	0.0737 (18)	0.0517 (15)	0.0505 (14)	−0.0154 (13)	0.0189 (13)	−0.0028 (11)
C15	0.083 (2)	0.0413 (14)	0.0679 (17)	−0.0163 (13)	0.0224 (15)	−0.0105 (12)
C16	0.0415 (12)	0.0516 (14)	0.0427 (12)	0.0000 (10)	−0.0005 (10)	−0.0098 (10)
C17	0.0665 (17)	0.0525 (15)	0.0505 (14)	−0.0034 (12)	0.0222 (13)	−0.0008 (11)
C18	0.0634 (16)	0.0433 (13)	0.0534 (14)	−0.0058 (11)	0.0154 (12)	−0.0002 (11)
C19	0.0432 (12)	0.0602 (15)	0.0404 (12)	0.0114 (11)	0.0086 (10)	−0.0079 (11)
C20	0.0603 (16)	0.0565 (16)	0.0538 (15)	0.0081 (12)	0.0128 (13)	0.0006 (12)
C21	0.0754 (19)	0.0662 (18)	0.0503 (15)	0.0279 (15)	0.0098 (14)	0.0069 (13)
C22	0.0489 (14)	0.084 (2)	0.0436 (14)	0.0202 (14)	−0.0008 (11)	−0.0151 (13)
C23	0.0506 (15)	0.0658 (17)	0.0620 (16)	0.0016 (13)	0.0112 (13)	−0.0082 (13)
C24	0.0551 (15)	0.0565 (15)	0.0467 (13)	0.0096 (12)	0.0083 (11)	0.0047 (11)
Cl1	0.0600 (4)	0.0764 (5)	0.0659 (4)	0.0030 (3)	0.0077 (3)	−0.0305 (4)
Cl2	0.0720 (6)	0.1432 (9)	0.0894 (6)	0.0396 (6)	−0.0326 (5)	−0.0372 (6)
N1	0.0429 (11)	0.0473 (12)	0.0622 (13)	0.0044 (9)	0.0137 (10)	0.0020 (10)
N2	0.0406 (10)	0.0485 (11)	0.0380 (10)	0.0053 (8)	0.0040 (8)	−0.0046 (8)
N3	0.0433 (11)	0.0438 (11)	0.0426 (10)	−0.0010 (8)	0.0044 (8)	−0.0071 (8)
O1	0.0486 (11)	0.0796 (13)	0.0634 (12)	0.0005 (9)	−0.0076 (9)	−0.0205 (10)
O2	0.0463 (10)	0.0751 (12)	0.0488 (9)	0.0156 (8)	−0.0012 (8)	−0.0203 (9)
S1	0.0652 (4)	0.0524 (4)	0.0564 (4)	0.0092 (3)	0.0213 (3)	−0.0062 (3)

Geometric parameters (Å, º) top

C1—C2	1.518 (4)	C12—O1	1.199 (3)
C1—H1A	0.9600	C12—N3	1.421 (3)
C1—H1B	0.9600	C13—C14	1.366 (3)
C1—H1C	0.9600	C13—C18	1.372 (3)
C2—C3	1.357 (3)	C13—N3	1.456 (3)
C2—S1	1.733 (3)	C14—C15	1.382 (3)
C3—C5	1.446 (3)	C14—H14	0.9300
C3—C4	1.499 (3)	C15—C16	1.364 (3)
C4—H4A	0.9600	C15—H15	0.9300
C4—H4B	0.9600	C16—C17	1.368 (3)
C4—H4C	0.9600	C16—Cl1	1.741 (2)
C5—C6	1.399 (3)	C17—C18	1.383 (3)
C5—C10	1.415 (3)	C17—H17	0.9300
C6—N1	1.327 (3)	C18—H18	0.9300
C6—S1	1.736 (2)	C19—C20	1.371 (4)
C7—N1	1.333 (3)	C19—C24	1.376 (4)
C7—C9	1.431 (3)	C19—O2	1.409 (3)
C7—C8	1.485 (3)	C20—C21	1.368 (4)
C8—H8A	0.9600	C20—H20	0.9300
C8—H8B	0.9600	C21—C22	1.374 (4)
C8—H8C	0.9600	C21—H21	0.9300
C9—C10	1.394 (3)	C22—C23	1.385 (4)
C9—C12	1.474 (3)	C22—Cl2	1.725 (3)
C10—N2	1.379 (3)	C23—C24	1.365 (4)
C11—N2	1.277 (3)	C23—H23	0.9300
C11—O2	1.343 (3)	C24—H24	0.9300
C11—N3	1.366 (3)

C2—C1—H1A	109.5	N3—C12—C9	113.70 (19)
C2—C1—H1B	109.5	C14—C13—C18	120.5 (2)
H1A—C1—H1B	109.5	C14—C13—N3	119.5 (2)
C2—C1—H1C	109.5	C18—C13—N3	119.8 (2)
H1A—C1—H1C	109.5	C13—C14—C15	119.7 (2)
H1B—C1—H1C	109.5	C13—C14—H14	120.2
C3—C2—C1	127.6 (2)	C15—C14—H14	120.2
C3—C2—S1	113.75 (18)	C16—C15—C14	119.5 (2)
C1—C2—S1	118.59 (19)	C16—C15—H15	120.3
C2—C3—C5	110.9 (2)	C14—C15—H15	120.3
C2—C3—C4	124.0 (2)	C15—C16—C17	121.3 (2)
C5—C3—C4	125.0 (2)	C15—C16—Cl1	119.21 (19)
C3—C4—H4A	109.5	C17—C16—Cl1	119.39 (19)
C3—C4—H4B	109.5	C16—C17—C18	119.0 (2)
H4A—C4—H4B	109.5	C16—C17—H17	120.5
C3—C4—H4C	109.5	C18—C17—H17	120.5
H4A—C4—H4C	109.5	C13—C18—C17	120.0 (2)
H4B—C4—H4C	109.5	C13—C18—H18	120.0
C6—C5—C10	114.8 (2)	C17—C18—H18	120.0
C6—C5—C3	113.5 (2)	C20—C19—C24	121.8 (2)
C10—C5—C3	131.7 (2)	C20—C19—O2	117.8 (2)
N1—C6—C5	128.1 (2)	C24—C19—O2	120.3 (2)
N1—C6—S1	121.63 (17)	C21—C20—C19	118.8 (3)
C5—C6—S1	110.31 (18)	C21—C20—H20	120.6
N1—C7—C9	121.2 (2)	C19—C20—H20	120.6
N1—C7—C8	115.5 (2)	C20—C21—C22	120.0 (3)
C9—C7—C8	123.2 (2)	C20—C21—H21	120.0
C7—C8—H8A	109.5	C22—C21—H21	120.0
C7—C8—H8B	109.5	C21—C22—C23	120.8 (3)
H8A—C8—H8B	109.5	C21—C22—Cl2	119.6 (2)
C7—C8—H8C	109.5	C23—C22—Cl2	119.5 (2)
H8A—C8—H8C	109.5	C24—C23—C22	119.2 (3)
H8B—C8—H8C	109.5	C24—C23—H23	120.4
C10—C9—C7	120.1 (2)	C22—C23—H23	120.4
C10—C9—C12	118.5 (2)	C23—C24—C19	119.4 (2)
C7—C9—C12	121.4 (2)	C23—C24—H24	120.3
N2—C10—C9	123.5 (2)	C19—C24—H24	120.3
N2—C10—C5	117.6 (2)	C6—N1—C7	116.91 (19)
C9—C10—C5	118.9 (2)	C11—N2—C10	116.78 (19)
N2—C11—O2	121.4 (2)	C11—N3—C12	121.03 (19)
N2—C11—N3	126.4 (2)	C11—N3—C13	120.10 (18)
O2—C11—N3	112.24 (19)	C12—N3—C13	118.84 (18)
O1—C12—N3	118.7 (2)	C11—O2—C19	116.21 (17)
O1—C12—C9	127.6 (2)	C2—S1—C6	91.57 (11)

C1—C2—C3—C5	180.0 (2)	C24—C19—C20—C21	−1.3 (4)
S1—C2—C3—C5	1.1 (2)	O2—C19—C20—C21	174.7 (2)
C1—C2—C3—C4	2.1 (4)	C19—C20—C21—C22	0.7 (4)
S1—C2—C3—C4	−176.76 (19)	C20—C21—C22—C23	−0.2 (4)
C2—C3—C5—C6	−0.4 (3)	C20—C21—C22—Cl2	−178.73 (19)
C4—C3—C5—C6	177.4 (2)	C21—C22—C23—C24	0.3 (4)
C2—C3—C5—C10	179.2 (2)	Cl2—C22—C23—C24	178.77 (19)
C4—C3—C5—C10	−2.9 (4)	C22—C23—C24—C19	−0.8 (4)
C10—C5—C6—N1	−0.2 (3)	C20—C19—C24—C23	1.4 (4)
C3—C5—C6—N1	179.5 (2)	O2—C19—C24—C23	−174.5 (2)
C10—C5—C6—S1	179.83 (15)	C5—C6—N1—C7	0.1 (4)
C3—C5—C6—S1	−0.5 (2)	S1—C6—N1—C7	−179.86 (17)
N1—C7—C9—C10	−1.1 (3)	C9—C7—N1—C6	0.5 (3)
C8—C7—C9—C10	179.2 (2)	C8—C7—N1—C6	−179.8 (2)
N1—C7—C9—C12	179.3 (2)	O2—C11—N2—C10	177.9 (2)
C8—C7—C9—C12	−0.4 (3)	N3—C11—N2—C10	−2.1 (4)
C7—C9—C10—N2	−178.9 (2)	C9—C10—N2—C11	1.3 (3)
C12—C9—C10—N2	0.7 (3)	C5—C10—N2—C11	−178.60 (19)
C7—C9—C10—C5	1.0 (3)	N2—C11—N3—C12	0.7 (4)
C12—C9—C10—C5	−179.33 (19)	O2—C11—N3—C12	−179.3 (2)
C6—C5—C10—N2	179.51 (19)	N2—C11—N3—C13	−177.5 (2)
C3—C5—C10—N2	−0.1 (3)	O2—C11—N3—C13	2.5 (3)
C6—C5—C10—C9	−0.4 (3)	O1—C12—N3—C11	−178.3 (2)
C3—C5—C10—C9	179.9 (2)	C9—C12—N3—C11	1.4 (3)
C10—C9—C12—O1	177.6 (2)	O1—C12—N3—C13	−0.1 (3)
C7—C9—C12—O1	−2.7 (4)	C9—C12—N3—C13	179.60 (18)
C10—C9—C12—N3	−2.0 (3)	C14—C13—N3—C11	97.7 (3)
C7—C9—C12—N3	177.67 (19)	C18—C13—N3—C11	−77.3 (3)
C18—C13—C14—C15	2.3 (4)	C14—C13—N3—C12	−80.5 (3)
N3—C13—C14—C15	−172.8 (2)	C18—C13—N3—C12	104.4 (3)
C13—C14—C15—C16	−0.7 (4)	N2—C11—O2—C19	1.2 (3)
C14—C15—C16—C17	−1.7 (4)	N3—C11—O2—C19	−178.8 (2)
C14—C15—C16—Cl1	174.8 (2)	C20—C19—O2—C11	107.2 (3)
C15—C16—C17—C18	2.5 (4)	C24—C19—O2—C11	−76.7 (3)
Cl1—C16—C17—C18	−174.0 (2)	C3—C2—S1—C6	−1.21 (19)
C14—C13—C18—C17	−1.4 (4)	C1—C2—S1—C6	179.8 (2)
N3—C13—C18—C17	173.6 (2)	N1—C6—S1—C2	−179.1 (2)
C16—C17—C18—C13	−1.0 (4)	C5—C6—S1—C2	0.91 (17)

Experimental details

Crystal data
Chemical formula	C₂₄H₁₇Cl₂N₃O₂S
M_r	482.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	292
a, b, c (Å)	11.1861 (17), 10.3346 (16), 19.517 (3)
β (°)	101.377 (3)
V (Å³)	2212.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.35 × 0.30 × 0.30

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.868, 0.885
No. of measured, independent and observed [I > 2σ(I)] reflections	12672, 4799, 3590
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.158, 1.10
No. of reflections	4799
No. of parameters	292
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.32

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.

Selected geometric parameters (Å, º) top

C2—S1	1.733 (3)	C11—N2	1.277 (3)
C6—N1	1.327 (3)	C11—O2	1.343 (3)
C6—S1	1.736 (2)	C11—N3	1.366 (3)
C7—N1	1.333 (3)	C12—O1	1.199 (3)
C10—N2	1.379 (3)	C12—N3	1.421 (3)

C3—C2—C1	127.6 (2)	N1—C7—C8	115.5 (2)
C3—C2—S1	113.75 (18)	N2—C10—C5	117.6 (2)
C1—C2—S1	118.59 (19)	N2—C11—O2	121.4 (2)
N1—C6—C5	128.1 (2)	O2—C11—N3	112.24 (19)
N1—C6—S1	121.63 (17)	O1—C12—N3	118.7 (2)
C5—C6—S1	110.31 (18)	N3—C12—C9	113.70 (19)
N1—C7—C9	121.2 (2)

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8-(4-Chloro­phen­oxy)-7-(4-chloro­phen­yl)-1,2,5-trimethylthieno[2',3';2,3]pyrido[4,5-d]pyrimidin-6(7H)-one

Supporting information

Key indicators

checkCIF/PLATON results

8-(4-Chlorophenoxy)-7-(4-chlorophenyl)-1,2,5-trimethylthieno[2',3';2,3]pyrido[4,5-d]pyrimidin-6(7H)-one