Crystal structure of 2-acetyl-5-(3-methoxyphenyl)-3,7-dimethyl-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate.

In the title mol-ecule, C20H22N2O4S, the pyrimidine ring is in a flattened half-chair conformation and the 3-meth-oxyphenyl substituent is in an axial arrangement. The thia-zole ring forms a dihedral angle of 81.3 (1)° with the benzene ring. In the crystal, weak C-H⋯S inter-actions link mol-ecules into chains along [001]. In addition, there are π-π inter-actions between inversion-related thia-zole rings with a centroid-centroid distance of 3.529 (2) Å. The ethyl group was refined as disordered over two sets of sites with an occupancy ratio of 0.52 (3):0.48 (2).

Related literature

For pharmacological and biological properties of pyrimidine derivatives, see: Alam et al. (2010a ▶,b ▶). For the therapeutic potential of thia­zolo­pyrimidine derivatives, see: Zhi et al. (2008 ▶). For related crystal structures, see: Jotani et al. (2010 ▶); Nagarajaiah et al. (2012 ▶).

Experimental

Crystal data

C20H22N2O4S

M = 386.46

Triclinic,

a = 8.281 (3) Å

b = 9.680 (4) Å

c = 12.821 (5) Å

α = 76.423 (10)°

β = 86.308 (10)°

γ = 74.641 (11)°

V = 963.3 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 100 K

0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.966, T max = 0.969

7744 measured reflections

4170 independent reflections

2529 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.173

S = 0.93

4170 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814023162/lh5730sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814023162/lh5730Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814023162/lh5730Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814023162/lh5730fig1.tif

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius. The primed atoms indicate the disorder.

Click here for additional data file.

. DOI: 10.1107/S1600536814023162/lh5730fig2.tif

Part of the crystal structure with weak C—H⋯S inter­actions shown as dashed lines. H atoms not involved in hydrogen bonding have been excluded.

CCDC reference: 1030239

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H22N2O4S	Z = 2
Mr = 386.46	F(000) = 408
Triclinic, P1	Dx = 1.332 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.281 (3) Å	Cell parameters from 2529 reflections
b = 9.680 (4) Å	θ = 2.2–27.0°
c = 12.821 (5) Å	µ = 0.20 mm−1
α = 76.423 (10)°	T = 100 K
β = 86.308 (10)°	Block, yellow
γ = 74.641 (11)°	0.18 × 0.16 × 0.16 mm
V = 963.3 (7) Å3

Bruker SMART APEX CCD-detector diffractometer	4170 independent reflections
Radiation source: fine-focus sealed tube	2529 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→10
Tmin = 0.966, Tmax = 0.969	k = −12→12
7744 measured reflections	l = −11→16

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.076P)2 + 0.6885P] where P = (Fo2 + 2Fc2)/3
4170 reflections	(Δ/σ)max < 0.001
263 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
S1	0.30579 (11)	0.36333 (9)	0.10093 (6)	0.0571 (3)
N1	0.3525 (3)	0.4674 (2)	−0.09649 (16)	0.0408 (5)
N2	0.1316 (3)	0.6205 (3)	−0.01435 (19)	0.0522 (6)
O1	0.6747 (4)	0.0390 (3)	0.0353 (3)	0.0991 (9)
O2	0.0460 (5)	0.9217 (3)	−0.3230 (3)	0.1344 (14)
O3	0.2781 (4)	0.7833 (3)	−0.37460 (18)	0.0887 (9)
O4	0.2791 (3)	0.3934 (3)	−0.53399 (17)	0.0815 (7)
C1	−0.0158 (5)	0.8666 (4)	−0.0993 (3)	0.0738 (10)
H1A	0.0392	0.9470	−0.1201	0.111*
H1B	−0.0530	0.8581	−0.0244	0.111*
H1C	−0.1128	0.8870	−0.1457	0.111*
C2	0.4657 (4)	0.2623 (3)	0.0315 (2)	0.0505 (7)
C3	0.4737 (3)	0.3342 (3)	−0.0718 (2)	0.0448 (6)
C4	0.5672 (5)	0.1135 (4)	0.0842 (3)	0.0678 (9)
C5	0.3089 (3)	0.5520 (3)	−0.2070 (2)	0.0422 (6)
H5	0.4132	0.5710	−0.2444	0.051*
C6	0.1873 (4)	0.6996 (3)	−0.2021 (2)	0.0474 (7)
C7	0.1055 (4)	0.7250 (3)	−0.1109 (2)	0.0505 (7)
C8	0.5262 (6)	0.0589 (5)	0.1991 (3)	0.0958 (14)
H8A	0.4158	0.0385	0.2040	0.144*
H8B	0.5249	0.1339	0.2392	0.144*
H8C	0.6109	−0.0315	0.2296	0.144*
C9	0.2502 (3)	0.5029 (3)	−0.0135 (2)	0.0435 (6)
C10	0.314 (4)	0.886 (2)	−0.4736 (17)	0.116 (7)	0.48 (3)
H10A	0.4280	0.8999	−0.4711	0.139*	0.48 (3)
H10B	0.2317	0.9832	−0.4829	0.139*	0.48 (3)
C10'	0.224 (2)	0.8853 (18)	−0.4809 (13)	0.085 (4)	0.52 (3)
H10C	0.1119	0.8797	−0.5001	0.102*	0.52 (3)
H10D	0.2164	0.9880	−0.4777	0.102*	0.52 (3)
C11	0.300 (2)	0.8136 (19)	−0.5624 (8)	0.102 (6)	0.48 (3)
H11A	0.4102	0.7506	−0.5754	0.152*	0.48 (3)
H11B	0.2622	0.8889	−0.6279	0.152*	0.48 (3)
H11C	0.2199	0.7537	−0.5422	0.152*	0.48 (3)
C11'	0.339 (2)	0.8426 (2)	−0.5548 (10)	0.182 (14)	0.52 (3)
H11D	0.4517	0.8313	−0.5285	0.273*	0.52 (3)
H11E	0.3191	0.9172	−0.6223	0.273*	0.52 (3)
H11F	0.3308	0.7485	−0.5669	0.273*	0.52 (3)
C12	0.2372 (2)	0.4638 (2)	−0.26787 (15)	0.0422 (6)
C13	0.2885 (2)	0.4605 (3)	−0.37231 (16)	0.0495 (7)
H13	0.3699	0.5105	−0.4044	0.059*
C14	0.2219 (4)	0.3846 (3)	−0.4306 (2)	0.0561 (8)
C15	0.1116 (4)	0.3055 (4)	−0.3822 (3)	0.0669 (9)
H15	0.0690	0.2502	−0.4208	0.080*
C16	0.0622 (4)	0.3063 (4)	−0.2764 (3)	0.0648 (9)
H16	−0.0144	0.2515	−0.2432	0.078*
C17	0.1232 (4)	0.3860 (3)	−0.2192 (2)	0.0504 (7)
H17	0.0876	0.3875	−0.1474	0.060*
C18	0.2065 (6)	0.3271 (5)	−0.6001 (3)	0.0995 (15)
H18A	0.2330	0.2206	−0.5711	0.149*
H18B	0.2517	0.3475	−0.6731	0.149*
H18C	0.0847	0.3676	−0.6019	0.149*
C19	0.1592 (5)	0.8125 (4)	−0.3027 (3)	0.0715 (10)
C20	0.5962 (4)	0.2884 (4)	−0.1555 (3)	0.0626 (8)
H20A	0.6810	0.1991	−0.1230	0.094*
H20B	0.6506	0.3673	−0.1864	0.094*
H20C	0.5375	0.2686	−0.2122	0.094*

	U11	U22	U33	U12	U13	U23
S1	0.0654 (5)	0.0657 (5)	0.0413 (4)	−0.0239 (4)	0.0025 (3)	−0.0068 (3)
N1	0.0435 (12)	0.0428 (11)	0.0375 (11)	−0.0094 (10)	0.0013 (9)	−0.0143 (9)
N2	0.0498 (14)	0.0546 (14)	0.0562 (15)	−0.0136 (12)	0.0120 (11)	−0.0231 (12)
O1	0.086 (2)	0.0692 (16)	0.123 (2)	0.0134 (15)	−0.0095 (18)	−0.0203 (16)
O2	0.163 (3)	0.090 (2)	0.097 (2)	0.038 (2)	−0.022 (2)	0.0100 (17)
O3	0.145 (3)	0.0573 (14)	0.0516 (14)	−0.0198 (15)	0.0099 (15)	0.0022 (11)
O4	0.1022 (19)	0.0988 (18)	0.0448 (13)	−0.0126 (15)	−0.0014 (12)	−0.0338 (12)
C1	0.065 (2)	0.0558 (19)	0.103 (3)	−0.0046 (17)	0.004 (2)	−0.0358 (19)
C2	0.0505 (17)	0.0482 (15)	0.0546 (17)	−0.0154 (14)	−0.0096 (13)	−0.0094 (13)
C3	0.0438 (15)	0.0420 (14)	0.0518 (16)	−0.0090 (12)	−0.0074 (12)	−0.0172 (12)
C4	0.063 (2)	0.060 (2)	0.082 (2)	−0.0211 (18)	−0.0222 (19)	−0.0070 (18)
C5	0.0461 (15)	0.0435 (14)	0.0367 (14)	−0.0118 (12)	0.0024 (11)	−0.0088 (11)
C6	0.0532 (17)	0.0395 (14)	0.0509 (16)	−0.0122 (13)	−0.0054 (13)	−0.0114 (12)
C7	0.0480 (17)	0.0445 (15)	0.0637 (19)	−0.0122 (13)	0.0008 (14)	−0.0215 (14)
C8	0.105 (3)	0.091 (3)	0.083 (3)	−0.042 (3)	−0.031 (2)	0.025 (2)
C9	0.0454 (15)	0.0511 (15)	0.0408 (14)	−0.0191 (13)	0.0057 (12)	−0.0176 (12)
C10	0.156 (18)	0.101 (8)	0.068 (9)	−0.029 (14)	0.018 (13)	0.017 (6)
C10'	0.103 (9)	0.066 (5)	0.064 (6)	−0.013 (7)	−0.008 (7)	0.020 (4)
C11	0.139 (12)	0.113 (10)	0.039 (7)	−0.022 (9)	−0.009 (7)	0.001 (6)
C11'	0.185 (19)	0.136 (14)	0.127 (17)	0.035 (13)	0.078 (15)	0.052 (13)
C12	0.0430 (15)	0.0424 (13)	0.0394 (14)	−0.0039 (12)	−0.0023 (11)	−0.0133 (11)
C13	0.0559 (18)	0.0520 (16)	0.0394 (15)	−0.0100 (14)	0.0015 (13)	−0.0126 (12)
C14	0.0628 (19)	0.0617 (18)	0.0406 (16)	−0.0011 (16)	−0.0048 (14)	−0.0211 (14)
C15	0.070 (2)	0.068 (2)	0.072 (2)	−0.0101 (18)	−0.0140 (18)	−0.0388 (18)
C16	0.062 (2)	0.069 (2)	0.075 (2)	−0.0282 (18)	0.0025 (17)	−0.0256 (17)
C17	0.0510 (17)	0.0561 (16)	0.0472 (16)	−0.0147 (14)	0.0023 (13)	−0.0176 (13)
C18	0.150 (4)	0.093 (3)	0.052 (2)	−0.004 (3)	−0.023 (2)	−0.035 (2)
C19	0.100 (3)	0.0505 (19)	0.060 (2)	−0.0115 (19)	−0.015 (2)	−0.0099 (16)
C20	0.0558 (19)	0.0620 (18)	0.067 (2)	0.0026 (15)	−0.0006 (16)	−0.0283 (16)

S1—C9	1.736 (3)	C8—H8C	0.9800
S1—C2	1.753 (3)	C10—C11	1.50 (4)
N1—C9	1.368 (3)	C10—H10A	0.9900
N1—C3	1.391 (3)	C10—H10B	0.9900
N1—C5	1.475 (3)	C10'—C11'	1.358 (19)
N2—C9	1.290 (4)	C10'—H10C	0.9900
N2—C7	1.391 (4)	C10'—H10D	0.9900
O1—C4	1.228 (4)	C11—H11A	0.9800
O2—C19	1.201 (4)	C11—H11B	0.9800
O3—C19	1.325 (4)	C11—H11C	0.9800
O3—C10	1.486 (18)	C11'—H11D	0.9800
O3—C10'	1.499 (15)	C11'—H11E	0.9800
O4—C14	1.370 (4)	C11'—H11F	0.9800
O4—C18	1.420 (4)	C12—C13	1.3835
C1—C7	1.502 (4)	C12—C17	1.389 (3)
C1—H1A	0.9800	C13—C14	1.388 (4)
C1—H1B	0.9800	C13—H13	0.9500
C1—H1C	0.9800	C14—C15	1.372 (5)
C2—C3	1.350 (4)	C15—C16	1.392 (5)
C2—C4	1.487 (4)	C15—H15	0.9500
C3—C20	1.491 (4)	C16—C17	1.382 (4)
C4—C8	1.493 (5)	C16—H16	0.9500
C5—C12	1.526 (3)	C17—H17	0.9500
C5—C6	1.527 (4)	C18—H18A	0.9800
C5—H5	1.0000	C18—H18B	0.9800
C6—C7	1.353 (4)	C18—H18C	0.9800
C6—C19	1.468 (4)	C20—H20A	0.9800
C8—H8A	0.9800	C20—H20B	0.9800
C8—H8B	0.9800	C20—H20C	0.9800
C9—S1—C2	91.44 (13)	C11—C10—H10B	110.9
C9—N1—C3	115.6 (2)	H10A—C10—H10B	108.9
C9—N1—C5	119.6 (2)	C11'—C10'—O3	107.3 (13)
C3—N1—C5	123.6 (2)	C11'—C10'—H10C	110.3
C9—N2—C7	116.3 (2)	O3—C10'—H10C	110.3
C19—O3—C10	127.2 (10)	C11'—C10'—H10D	110.3
C19—O3—C10'	108.8 (8)	O3—C10'—H10D	110.3
C14—O4—C18	117.5 (3)	H10C—C10'—H10D	108.5
C7—C1—H1A	109.5	C10'—C11'—H11D	109.5
C7—C1—H1B	109.5	C10'—C11'—H11E	109.5
H1A—C1—H1B	109.5	H11D—C11'—H11E	109.5
C7—C1—H1C	109.5	C10'—C11'—H11F	109.5
H1A—C1—H1C	109.5	H11D—C11'—H11F	109.5
H1B—C1—H1C	109.5	H11E—C11'—H11F	109.5
C3—C2—C4	127.6 (3)	C13—C12—C17	119.90 (16)
C3—C2—S1	111.2 (2)	C13—C12—C5	119.31 (16)
C4—C2—S1	121.2 (2)	C17—C12—C5	120.8 (2)
C2—C3—N1	112.5 (2)	C12—C13—C14	120.55 (19)
C2—C3—C20	127.7 (3)	C12—C13—H13	119.7
N1—C3—C20	119.8 (2)	C14—C13—H13	119.7
O1—C4—C2	121.9 (3)	O4—C14—C15	125.4 (3)
O1—C4—C8	122.3 (4)	O4—C14—C13	114.9 (3)
C2—C4—C8	115.8 (3)	C15—C14—C13	119.7 (3)
N1—C5—C12	110.26 (19)	C14—C15—C16	119.9 (3)
N1—C5—C6	108.5 (2)	C14—C15—H15	120.1
C12—C5—C6	112.6 (2)	C16—C15—H15	120.1
N1—C5—H5	108.5	C17—C16—C15	120.8 (3)
C12—C5—H5	108.5	C17—C16—H16	119.6
C6—C5—H5	108.5	C15—C16—H16	119.6
C7—C6—C19	121.2 (3)	C16—C17—C12	119.2 (3)
C7—C6—C5	122.3 (2)	C16—C17—H17	120.4
C19—C6—C5	116.5 (3)	C12—C17—H17	120.4
C6—C7—N2	122.2 (3)	O4—C18—H18A	109.5
C6—C7—C1	125.6 (3)	O4—C18—H18B	109.5
N2—C7—C1	112.1 (3)	H18A—C18—H18B	109.5
C4—C8—H8A	109.5	O4—C18—H18C	109.5
C4—C8—H8B	109.5	H18A—C18—H18C	109.5
H8A—C8—H8B	109.5	H18B—C18—H18C	109.5
C4—C8—H8C	109.5	O2—C19—O3	120.5 (3)
H8A—C8—H8C	109.5	O2—C19—C6	127.3 (4)
H8B—C8—H8C	109.5	O3—C19—C6	112.2 (3)
N2—C9—N1	127.9 (3)	C3—C20—H20A	109.5
N2—C9—S1	122.8 (2)	C3—C20—H20B	109.5
N1—C9—S1	109.3 (2)	H20A—C20—H20B	109.5
O3—C10—C11	104.5 (18)	C3—C20—H20C	109.5
O3—C10—H10A	110.9	H20A—C20—H20C	109.5
C11—C10—H10A	110.9	H20B—C20—H20C	109.5
O3—C10—H10B	110.9
C9—S1—C2—C3	0.6 (2)	C3—N1—C9—S1	−0.6 (3)
C9—S1—C2—C4	−176.3 (2)	C5—N1—C9—S1	167.21 (17)
C4—C2—C3—N1	175.6 (3)	C2—S1—C9—N2	−178.8 (2)
S1—C2—C3—N1	−1.0 (3)	C2—S1—C9—N1	−0.02 (19)
C4—C2—C3—C20	−6.0 (5)	C19—O3—C10—C11	−122.6 (13)
S1—C2—C3—C20	177.3 (2)	C10'—O3—C10—C11	−64 (3)
C9—N1—C3—C2	1.1 (3)	C19—O3—C10'—C11'	−173.7 (13)
C5—N1—C3—C2	−166.2 (2)	C10—O3—C10'—C11'	52 (3)
C9—N1—C3—C20	−177.4 (2)	N1—C5—C12—C13	−136.62 (19)
C5—N1—C3—C20	15.4 (4)	C6—C5—C12—C13	102.0 (2)
C3—C2—C4—O1	0.5 (5)	N1—C5—C12—C17	42.6 (3)
S1—C2—C4—O1	176.9 (3)	C6—C5—C12—C17	−78.8 (3)
C3—C2—C4—C8	−177.6 (3)	C17—C12—C13—C14	2.6 (3)
S1—C2—C4—C8	−1.2 (4)	C5—C12—C13—C14	−178.2 (2)
C9—N1—C5—C12	−103.6 (2)	C18—O4—C14—C15	6.5 (5)
C3—N1—C5—C12	63.1 (3)	C18—O4—C14—C13	−175.5 (3)
C9—N1—C5—C6	20.1 (3)	C12—C13—C14—O4	178.1 (2)
C3—N1—C5—C6	−173.1 (2)	C12—C13—C14—C15	−3.8 (4)
N1—C5—C6—C7	−15.3 (3)	O4—C14—C15—C16	−179.6 (3)
C12—C5—C6—C7	107.0 (3)	C13—C14—C15—C16	2.5 (5)
N1—C5—C6—C19	166.4 (2)	C14—C15—C16—C17	−0.1 (5)
C12—C5—C6—C19	−71.2 (3)	C15—C16—C17—C12	−1.1 (5)
C19—C6—C7—N2	−179.1 (3)	C13—C12—C17—C16	−0.2 (4)
C5—C6—C7—N2	2.7 (4)	C5—C12—C17—C16	−179.4 (3)
C19—C6—C7—C1	−1.8 (5)	C10—O3—C19—O2	14.9 (17)
C5—C6—C7—C1	−180.0 (3)	C10'—O3—C19—O2	−11.8 (9)
C9—N2—C7—C6	6.6 (4)	C10—O3—C19—C6	−164.6 (16)
C9—N2—C7—C1	−171.1 (2)	C10'—O3—C19—C6	168.8 (8)
C7—N2—C9—N1	−0.9 (4)	C7—C6—C19—O2	−15.5 (6)
C7—N2—C9—S1	177.68 (19)	C5—C6—C19—O2	162.8 (4)
C3—N1—C9—N2	178.1 (2)	C7—C6—C19—O3	163.9 (3)
C5—N1—C9—N2	−14.1 (4)	C5—C6—C19—O3	−17.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···S1i	0.98	2.87	3.822 (3)	162

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C18H18BS1i	0.98	2.87	3.822(3)	162

Symmetry code: (i) .