Ethyl 7-methyl-2-((1-methyl-1H-pyrrol-2-yl)methyl-ene)-3-oxo-5-phenyl-3,5-dihydro-2H-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

In the structure of the title compound, C(22)H(21)N(3)O(3)S, the thia-zole ring forms dihedral angles of 88.83 (7) and 9.39 (9)°, respectively, with the benzene and pyrrole rings. The dihydro-pyrimidine ring adopts a flattened boat conformation. The olefinic double bond is in a Z conformation.

Related literature

For related structures, see: Hou (2009 ▶); Zhao et al. (2011 ▶). For background to the biological properties of fused thia­zolo[3,2-a]pyrimidine derivatives, see: Ashok et al. (2007 ▶); Bahekar & Shinde (2004 ▶); Hurst & Hull (1961 ▶); Mehta et al. (2006 ▶); Shah & Desai (2007 ▶); Srivastava et al. (2006 ▶); Subudhi et al. (2007 ▶); Magerramov et al. (2006 ▶); Zhou et al. (2008 ▶).

Experimental

Crystal data

C22H21N3O3S

M = 407.48

Monoclinic,

a = 11.8187 (10) Å

b = 10.2911 (9) Å

c = 16.2290 (14) Å

β = 90.584 (2)°

V = 1973.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 293 K

0.32 × 0.24 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.814, T max = 1.000

10415 measured reflections

3877 independent reflections

3433 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.109

S = 1.05

3877 reflections

265 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812041748/aa2075sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041748/aa2075Isup2.hkl

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

C22H21N3O3S	F(000) = 856
Mr = 407.48	Dx = 1.371 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4867 reflections
a = 11.8187 (10) Å	θ = 5.0–56.3°
b = 10.2911 (9) Å	µ = 0.19 mm−1
c = 16.2290 (14) Å	T = 293 K
β = 90.584 (2)°	Prismatic, red
V = 1973.8 (3) Å3	0.32 × 0.24 × 0.16 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3877 independent reflections
Radiation source: fine-focus sealed tube	3433 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
phi and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −14→14
Tmin = 0.814, Tmax = 1.000	k = −12→11
10415 measured reflections	l = −20→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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0574P)2 + 0.5784P] where P = (Fo2 + 2Fc2)/3
3877 reflections	(Δ/σ)max < 0.001
265 parameters	Δρmax = 0.30 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.

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	0.45859 (3)	0.25287 (4)	0.01131 (2)	0.04128 (14)
N1	0.36364 (10)	0.46192 (12)	0.06560 (7)	0.0318 (3)
N2	0.26786 (11)	0.35881 (14)	−0.04481 (8)	0.0402 (3)
N3	0.76832 (11)	0.15037 (14)	0.18041 (8)	0.0413 (3)
O1	0.48083 (10)	0.52724 (11)	0.17107 (8)	0.0471 (3)
O2	0.05024 (13)	0.69653 (15)	−0.05111 (10)	0.0735 (5)
O3	0.14144 (10)	0.76092 (11)	0.06154 (7)	0.0473 (3)
C1	0.45910 (12)	0.45135 (15)	0.11618 (9)	0.0337 (3)
C2	0.52334 (12)	0.33419 (15)	0.09404 (9)	0.0343 (3)
C3	0.34879 (12)	0.36725 (15)	0.00763 (9)	0.0338 (3)
C4	0.19135 (13)	0.46391 (15)	−0.04784 (9)	0.0362 (3)
C5	0.19370 (12)	0.56033 (15)	0.00841 (9)	0.0336 (3)
C6	0.27014 (12)	0.55164 (14)	0.08448 (9)	0.0316 (3)
H6	0.3014	0.6379	0.0965	0.038*
C7	0.20515 (11)	0.50354 (15)	0.15961 (9)	0.0330 (3)
C8	0.16948 (14)	0.59098 (18)	0.21843 (10)	0.0446 (4)
H8	0.1883	0.6784	0.2138	0.054*
C9	0.10566 (17)	0.5486 (2)	0.28426 (11)	0.0588 (5)
H9	0.0809	0.6081	0.3233	0.071*
C10	0.07856 (16)	0.4197 (2)	0.29245 (11)	0.0573 (5)
H10	0.0360	0.3919	0.3370	0.069*
C11	0.11433 (15)	0.3322 (2)	0.23496 (11)	0.0520 (4)
H11	0.0967	0.2446	0.2406	0.062*
C12	0.17686 (14)	0.37389 (17)	0.16826 (10)	0.0422 (4)
H12	0.2001	0.3141	0.1289	0.051*
C13	0.11228 (15)	0.45209 (19)	−0.12025 (11)	0.0485 (4)
H13A	0.0502	0.5112	−0.1137	0.073*
H13B	0.0840	0.3648	−0.1235	0.073*
H13C	0.1520	0.4728	−0.1699	0.073*
C14	0.12023 (13)	0.67570 (16)	0.00121 (10)	0.0396 (4)
C15	0.07470 (16)	0.87886 (19)	0.05991 (13)	0.0561 (5)
H15A	−0.0034	0.8591	0.0727	0.067*
H15B	0.0768	0.9173	0.0054	0.067*
C16	0.1209 (2)	0.9705 (3)	0.12081 (18)	0.0907 (9)
H16A	0.1136	0.9345	0.1751	0.136*
H16B	0.0799	1.0509	0.1176	0.136*
H16C	0.1993	0.9861	0.1096	0.136*
C17	0.61539 (12)	0.29575 (16)	0.13690 (10)	0.0371 (3)
H17	0.6411	0.3529	0.1773	0.045*
C18	0.67851 (12)	0.17881 (16)	0.12828 (10)	0.0384 (4)
C19	0.66600 (15)	0.07268 (18)	0.07624 (12)	0.0503 (4)
H19	0.6123	0.0643	0.0343	0.060*
C20	0.74750 (17)	−0.01876 (19)	0.09753 (13)	0.0572 (5)
H20	0.7581	−0.0994	0.0729	0.069*
C21	0.80908 (15)	0.03176 (18)	0.16125 (12)	0.0516 (4)
H21	0.8697	−0.0091	0.1875	0.062*
C22	0.81581 (16)	0.23339 (19)	0.24420 (13)	0.0548 (5)
H22A	0.8705	0.1853	0.2760	0.082*
H22B	0.7565	0.2628	0.2796	0.082*
H22C	0.8518	0.3069	0.2192	0.082*

	U11	U22	U33	U12	U13	U23
S1	0.0416 (2)	0.0415 (2)	0.0407 (2)	0.01238 (17)	−0.00433 (17)	−0.00727 (16)
N1	0.0271 (6)	0.0325 (7)	0.0358 (6)	0.0032 (5)	−0.0009 (5)	−0.0010 (5)
N2	0.0418 (7)	0.0412 (8)	0.0373 (7)	0.0070 (6)	−0.0067 (6)	−0.0036 (6)
N3	0.0334 (7)	0.0417 (8)	0.0488 (8)	0.0044 (6)	−0.0002 (6)	0.0088 (6)
O1	0.0408 (6)	0.0430 (7)	0.0573 (7)	0.0047 (5)	−0.0145 (5)	−0.0128 (6)
O2	0.0766 (10)	0.0619 (9)	0.0813 (10)	0.0293 (8)	−0.0421 (8)	−0.0117 (8)
O3	0.0500 (7)	0.0418 (7)	0.0499 (7)	0.0171 (5)	−0.0098 (5)	−0.0021 (5)
C1	0.0281 (7)	0.0335 (8)	0.0396 (8)	−0.0014 (6)	−0.0007 (6)	0.0012 (6)
C2	0.0296 (7)	0.0346 (8)	0.0388 (8)	0.0004 (6)	0.0019 (6)	0.0010 (6)
C3	0.0346 (7)	0.0338 (8)	0.0331 (7)	0.0041 (6)	0.0019 (6)	0.0005 (6)
C4	0.0334 (7)	0.0393 (8)	0.0359 (7)	0.0015 (6)	−0.0023 (6)	0.0039 (6)
C5	0.0289 (7)	0.0357 (8)	0.0363 (7)	0.0019 (6)	−0.0008 (6)	0.0055 (6)
C6	0.0283 (7)	0.0288 (7)	0.0376 (8)	0.0036 (6)	−0.0016 (6)	−0.0014 (6)
C7	0.0263 (7)	0.0398 (8)	0.0328 (7)	0.0047 (6)	−0.0051 (6)	−0.0007 (6)
C8	0.0474 (9)	0.0451 (10)	0.0413 (9)	0.0062 (8)	−0.0028 (7)	−0.0075 (7)
C9	0.0566 (11)	0.0806 (15)	0.0395 (9)	0.0131 (10)	0.0064 (8)	−0.0122 (9)
C10	0.0463 (10)	0.0845 (16)	0.0412 (9)	0.0007 (10)	0.0076 (8)	0.0094 (9)
C11	0.0436 (9)	0.0572 (11)	0.0554 (10)	−0.0039 (8)	0.0033 (8)	0.0114 (9)
C12	0.0403 (8)	0.0430 (9)	0.0433 (9)	0.0009 (7)	0.0033 (7)	−0.0006 (7)
C13	0.0467 (9)	0.0545 (11)	0.0442 (9)	0.0063 (8)	−0.0121 (7)	−0.0035 (8)
C14	0.0358 (8)	0.0402 (9)	0.0427 (8)	0.0044 (7)	−0.0033 (7)	0.0062 (7)
C15	0.0539 (11)	0.0439 (10)	0.0703 (12)	0.0189 (8)	−0.0066 (9)	−0.0017 (9)
C16	0.0925 (18)	0.0751 (17)	0.1037 (19)	0.0376 (14)	−0.0330 (15)	−0.0384 (14)
C17	0.0305 (7)	0.0371 (8)	0.0437 (8)	0.0001 (6)	−0.0004 (6)	0.0003 (7)
C18	0.0294 (7)	0.0393 (9)	0.0465 (9)	0.0029 (6)	0.0007 (6)	0.0054 (7)
C19	0.0444 (9)	0.0479 (10)	0.0584 (11)	0.0083 (8)	−0.0045 (8)	−0.0052 (8)
C20	0.0566 (11)	0.0425 (10)	0.0725 (13)	0.0140 (9)	0.0016 (10)	−0.0040 (9)
C21	0.0438 (9)	0.0447 (10)	0.0663 (12)	0.0142 (8)	0.0024 (8)	0.0129 (9)
C22	0.0479 (10)	0.0532 (11)	0.0628 (12)	0.0022 (8)	−0.0167 (9)	0.0072 (9)

S1—C2	1.7515 (15)	C9—H9	0.9300
S1—C3	1.7525 (15)	C10—C11	1.367 (3)
N1—C3	1.3644 (19)	C10—H10	0.9300
N1—C1	1.3927 (18)	C11—C12	1.385 (2)
N1—C6	1.4747 (18)	C11—H11	0.9300
N2—C3	1.2767 (19)	C12—H12	0.9300
N2—C4	1.410 (2)	C13—H13A	0.9600
N3—C21	1.350 (2)	C13—H13B	0.9600
N3—C18	1.382 (2)	C13—H13C	0.9600
N3—C22	1.451 (2)	C15—C16	1.467 (3)
O1—C1	1.2103 (18)	C15—H15A	0.9700
O2—C14	1.1986 (19)	C15—H15B	0.9700
O3—C14	1.336 (2)	C16—H16A	0.9600
O3—C15	1.448 (2)	C16—H16B	0.9600
C1—C2	1.471 (2)	C16—H16C	0.9600
C2—C17	1.345 (2)	C17—C18	1.424 (2)
C4—C5	1.348 (2)	C17—H17	0.9300
C4—C13	1.499 (2)	C18—C19	1.388 (2)
C5—C14	1.475 (2)	C19—C20	1.388 (3)
C5—C6	1.525 (2)	C19—H19	0.9300
C6—C7	1.530 (2)	C20—C21	1.362 (3)
C6—H6	0.9800	C20—H20	0.9300
C7—C8	1.381 (2)	C21—H21	0.9300
C7—C12	1.383 (2)	C22—H22A	0.9600
C8—C9	1.384 (3)	C22—H22B	0.9600
C8—H8	0.9300	C22—H22C	0.9600
C9—C10	1.371 (3)
C2—S1—C3	91.30 (7)	C7—C12—C11	120.65 (16)
C3—N1—C1	116.64 (12)	C7—C12—H12	119.7
C3—N1—C6	119.93 (12)	C11—C12—H12	119.7
C1—N1—C6	122.05 (12)	C4—C13—H13A	109.5
C3—N2—C4	116.54 (13)	C4—C13—H13B	109.5
C21—N3—C18	108.92 (15)	H13A—C13—H13B	109.5
C21—N3—C22	124.10 (15)	C4—C13—H13C	109.5
C18—N3—C22	126.96 (14)	H13A—C13—H13C	109.5
C14—O3—C15	116.02 (13)	H13B—C13—H13C	109.5
O1—C1—N1	123.23 (14)	O2—C14—O3	121.64 (15)
O1—C1—C2	127.04 (14)	O2—C14—C5	126.98 (16)
N1—C1—C2	109.69 (12)	O3—C14—C5	111.37 (13)
C17—C2—C1	122.10 (14)	O3—C15—C16	109.13 (16)
C17—C2—S1	126.93 (13)	O3—C15—H15A	109.9
C1—C2—S1	110.87 (10)	C16—C15—H15A	109.9
N2—C3—N1	126.75 (14)	O3—C15—H15B	109.9
N2—C3—S1	121.76 (12)	C16—C15—H15B	109.9
N1—C3—S1	111.48 (10)	H15A—C15—H15B	108.3
C5—C4—N2	122.14 (13)	C15—C16—H16A	109.5
C5—C4—C13	126.79 (15)	C15—C16—H16B	109.5
N2—C4—C13	111.07 (14)	H16A—C16—H16B	109.5
C4—C5—C14	122.06 (14)	C15—C16—H16C	109.5
C4—C5—C6	120.85 (13)	H16A—C16—H16C	109.5
C14—C5—C6	117.05 (13)	H16B—C16—H16C	109.5
N1—C6—C5	107.91 (11)	C2—C17—C18	128.30 (15)
N1—C6—C7	110.27 (12)	C2—C17—H17	115.8
C5—C6—C7	111.47 (11)	C18—C17—H17	115.8
N1—C6—H6	109.0	N3—C18—C19	106.40 (14)
C5—C6—H6	109.0	N3—C18—C17	121.26 (15)
C7—C6—H6	109.0	C19—C18—C17	132.26 (15)
C8—C7—C12	118.85 (15)	C18—C19—C20	108.23 (17)
C8—C7—C6	119.96 (15)	C18—C19—H19	125.9
C12—C7—C6	121.13 (13)	C20—C19—H19	125.9
C7—C8—C9	120.06 (18)	C21—C20—C19	107.12 (17)
C7—C8—H8	120.0	C21—C20—H20	126.4
C9—C8—H8	120.0	C19—C20—H20	126.4
C10—C9—C8	120.59 (18)	N3—C21—C20	109.33 (16)
C10—C9—H9	119.7	N3—C21—H21	125.3
C8—C9—H9	119.7	C20—C21—H21	125.3
C11—C10—C9	119.81 (17)	N3—C22—H22A	109.5
C11—C10—H10	120.1	N3—C22—H22B	109.5
C9—C10—H10	120.1	H22A—C22—H22B	109.5
C10—C11—C12	120.04 (19)	N3—C22—H22C	109.5
C10—C11—H11	120.0	H22A—C22—H22C	109.5
C12—C11—H11	120.0	H22B—C22—H22C	109.5
C3—N1—C1—O1	−178.40 (14)	C5—C6—C7—C8	−101.17 (16)
C6—N1—C1—O1	−11.8 (2)	N1—C6—C7—C12	−43.80 (18)
C3—N1—C1—C2	−0.46 (18)	C5—C6—C7—C12	76.03 (17)
C6—N1—C1—C2	166.11 (12)	C12—C7—C8—C9	−0.6 (2)
O1—C1—C2—C17	2.4 (2)	C6—C7—C8—C9	176.68 (15)
N1—C1—C2—C17	−175.41 (14)	C7—C8—C9—C10	0.9 (3)
O1—C1—C2—S1	179.05 (14)	C8—C9—C10—C11	−0.3 (3)
N1—C1—C2—S1	1.22 (15)	C9—C10—C11—C12	−0.6 (3)
C3—S1—C2—C17	175.15 (15)	C8—C7—C12—C11	−0.3 (2)
C3—S1—C2—C1	−1.27 (11)	C6—C7—C12—C11	−177.55 (14)
C4—N2—C3—N1	5.9 (2)	C10—C11—C12—C7	0.9 (3)
C4—N2—C3—S1	−173.22 (11)	C15—O3—C14—O2	0.3 (2)
C1—N1—C3—N2	−179.70 (15)	C15—O3—C14—C5	179.36 (14)
C6—N1—C3—N2	13.4 (2)	C4—C5—C14—O2	2.3 (3)
C1—N1—C3—S1	−0.50 (16)	C6—C5—C14—O2	−175.46 (18)
C6—N1—C3—S1	−167.38 (10)	C4—C5—C14—O3	−176.79 (14)
C2—S1—C3—N2	−179.73 (14)	C6—C5—C14—O3	5.49 (19)
C2—S1—C3—N1	1.03 (11)	C14—O3—C15—C16	−170.47 (19)
C3—N2—C4—C5	−8.6 (2)	C1—C2—C17—C18	172.86 (15)
C3—N2—C4—C13	170.92 (14)	S1—C2—C17—C18	−3.2 (3)
N2—C4—C5—C14	174.67 (14)	C21—N3—C18—C19	−0.08 (18)
C13—C4—C5—C14	−4.7 (2)	C22—N3—C18—C19	178.08 (16)
N2—C4—C5—C6	−7.7 (2)	C21—N3—C18—C17	177.00 (14)
C13—C4—C5—C6	172.92 (15)	C22—N3—C18—C17	−4.8 (2)
C3—N1—C6—C5	−26.08 (17)	C2—C17—C18—N3	−176.53 (15)
C1—N1—C6—C5	167.78 (13)	C2—C17—C18—C19	−0.3 (3)
C3—N1—C6—C7	95.89 (15)	N3—C18—C19—C20	0.3 (2)
C1—N1—C6—C7	−70.25 (17)	C17—C18—C19—C20	−176.32 (17)
C4—C5—C6—N1	23.55 (19)	C18—C19—C20—C21	−0.4 (2)
C14—C5—C6—N1	−158.71 (12)	C18—N3—C21—C20	−0.2 (2)
C4—C5—C6—C7	−97.67 (16)	C22—N3—C21—C20	−178.41 (17)
C14—C5—C6—C7	80.07 (16)	C19—C20—C21—N3	0.4 (2)
N1—C6—C7—C8	139.00 (14)