Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053780/tk2207sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053780/tk2207Isup2.hkl |
CCDC reference: 651561
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.005 Å
- R factor = 0.044
- wR factor = 0.094
- Data-to-parameter ratio = 17.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. S1 .. 3.59 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C7 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 5 Informative message, check
Ethyl 5-(4-chlorophenyl)-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate was prepared according to the literature method (Ranu et al., 2002). This compound (1 mmol) and 1-bromopropan-2-one (1 mmol) were successively added to water (5 ml) in a test tube and the reaction mixture was vigorously refluxed for 24 h. The system was cooled to room temperature and filtered to isolate the crude product. The analytical sample was obtained by recrystallization of the crude product from ethanol. The solid was isolated, washed three times with ethanol and dried in a vacuum desiccator; yield 92%, m.p. 513–514 K. IR: 3110, 2980, 1688, 1630, 1600, 1511, 1500 cm-1; 1H NMR: 1.22 (t, J = 7.2 Hz, 3H), 2.00 (s, 3H), 2.55 (s, 3H), 4.10–4.21 (m, 2H), 6.27 (s, 1H), 7.10 (s, 1H), 7.14–7.24 (m, 2H), 7.26–7.29 p.p.m. (m, 2H). Analysis found: C 47.51, H 4.22, N 6.52%; C17H18BrN2O2S requires: C 47.60, H 4.29, N 6.48%. Single crystals suitable for crystallography were obtained by the slow evaporation of an ethanol solution of (I).
The H atom bonded to N atom was located in a difference map and refined with Uiso(H) = 1.2Ueq(N) so that N—H = 0.86 (1) Å. Other H atoms were positioned geometrically and refined using a riding model approximation with C—H = 0.93–0.98 Å and with Uiso(H) = 1.2–1.5Ueq(C).
Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
Fig. 1. The molecular structure of (I), showing the atom-numbering scheme and 30% probability displacement ellipsoids. |
C17H18ClN2O2S+·Br− | F(000) = 1744 |
Mr = 429.75 | Dx = 1.407 Mg m−3 |
Monoclinic, C2/c | Melting point = 513–514 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 25.457 (2) Å | Cell parameters from 2973 reflections |
b = 11.697 (2) Å | θ = 2.3–25.5° |
c = 14.231 (3) Å | µ = 2.27 mm−1 |
β = 106.8080 (16)° | T = 291 K |
V = 4056.5 (12) Å3 | Block, colourless |
Z = 8 | 0.30 × 0.26 × 0.24 mm |
Bruker SMART APEX CCD diffractometer | 3986 independent reflections |
Radiation source: sealed tube | 2937 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ϕ and ω scans | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −29→31 |
Tmin = 0.505, Tmax = 0.584 | k = −14→13 |
10641 measured reflections | l = −17→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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0421P)2 + 1.5186P] where P = (Fo2 + 2Fc2)/3 |
3986 reflections | (Δ/σ)max < 0.001 |
223 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C17H18ClN2O2S+·Br− | V = 4056.5 (12) Å3 |
Mr = 429.75 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 25.457 (2) Å | µ = 2.27 mm−1 |
b = 11.697 (2) Å | T = 291 K |
c = 14.231 (3) Å | 0.30 × 0.26 × 0.24 mm |
β = 106.8080 (16)° |
Bruker SMART APEX CCD diffractometer | 3986 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2937 reflections with I > 2σ(I) |
Tmin = 0.505, Tmax = 0.584 | Rint = 0.031 |
10641 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.26 e Å−3 |
3986 reflections | Δρmin = −0.29 e Å−3 |
223 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 | ||
Br1 | 0.193130 (15) | 0.08363 (3) | 0.11668 (3) | 0.06287 (14) | |
C1 | 0.05124 (13) | 0.2550 (3) | 0.5811 (2) | 0.0529 (8) | |
C2 | 0.00250 (15) | 0.2082 (3) | 0.5272 (3) | 0.0606 (9) | |
H2 | 0.0025 | 0.1379 | 0.4966 | 0.073* | |
C3 | −0.04725 (15) | 0.2644 (3) | 0.5177 (3) | 0.0681 (10) | |
H3 | −0.0803 | 0.2330 | 0.4808 | 0.082* | |
C4 | −0.04561 (15) | 0.3696 (3) | 0.5654 (3) | 0.0621 (9) | |
C5 | 0.00383 (16) | 0.4186 (3) | 0.6183 (3) | 0.0685 (10) | |
H5 | 0.0042 | 0.4902 | 0.6469 | 0.082* | |
C6 | 0.05217 (14) | 0.3609 (3) | 0.6283 (3) | 0.0603 (9) | |
H6 | 0.0853 | 0.3916 | 0.6659 | 0.072* | |
C7 | 0.10663 (12) | 0.1866 (3) | 0.5932 (2) | 0.0456 (7) | |
H7 | 0.0983 | 0.1127 | 0.5597 | 0.055* | |
C8 | 0.14678 (12) | 0.2529 (3) | 0.5513 (2) | 0.0467 (7) | |
C9 | 0.19109 (13) | 0.3174 (3) | 0.6071 (2) | 0.0527 (8) | |
S1 | 0.19598 (4) | 0.18989 (8) | 0.88153 (6) | 0.0567 (2) | |
C10 | 0.17799 (13) | 0.2276 (3) | 0.7561 (2) | 0.0530 (8) | |
C11 | 0.14183 (14) | 0.0864 (3) | 0.8572 (3) | 0.0602 (9) | |
H11 | 0.1333 | 0.0420 | 0.9050 | 0.072* | |
C12 | 0.11427 (14) | 0.0811 (3) | 0.7576 (3) | 0.0560 (8) | |
C13 | 0.06841 (13) | 0.0014 (3) | 0.7070 (3) | 0.0637 (10) | |
H13A | 0.0659 | −0.0591 | 0.7511 | 0.096* | |
H13B | 0.0756 | −0.0303 | 0.6498 | 0.096* | |
H13C | 0.0344 | 0.0429 | 0.6880 | 0.096* | |
C14 | 0.23141 (13) | 0.3942 (3) | 0.5837 (3) | 0.0580 (9) | |
H14A | 0.2168 | 0.4228 | 0.5180 | 0.087* | |
H14B | 0.2647 | 0.3528 | 0.5886 | 0.087* | |
H14C | 0.2391 | 0.4570 | 0.6290 | 0.087* | |
C15 | 0.13101 (13) | 0.2443 (3) | 0.4422 (2) | 0.0489 (7) | |
C16 | 0.14414 (14) | 0.3068 (3) | 0.2878 (2) | 0.0578 (8) | |
H16A | 0.1052 | 0.3235 | 0.2631 | 0.069* | |
H16B | 0.1504 | 0.2310 | 0.2656 | 0.069* | |
C17 | 0.17647 (16) | 0.3939 (3) | 0.2484 (3) | 0.0656 (10) | |
H17C | 0.2148 | 0.3753 | 0.2708 | 0.098* | |
H17D | 0.1707 | 0.4687 | 0.2715 | 0.098* | |
H17E | 0.1643 | 0.3930 | 0.1780 | 0.098* | |
Cl1 | −0.10751 (4) | 0.44589 (8) | 0.55951 (7) | 0.0653 (2) | |
N1 | 0.20339 (11) | 0.3071 (3) | 0.7143 (2) | 0.0524 (7) | |
H1A | 0.2272 (15) | 0.352 (3) | 0.751 (3) | 0.063* | |
N2 | 0.13435 (11) | 0.1668 (2) | 0.70220 (18) | 0.0512 (6) | |
O1 | 0.09178 (10) | 0.1876 (2) | 0.39502 (17) | 0.0640 (6) | |
O2 | 0.16151 (9) | 0.31004 (19) | 0.39710 (16) | 0.0576 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0658 (2) | 0.0651 (2) | 0.0608 (2) | 0.02571 (17) | 0.02317 (17) | 0.01386 (17) |
C1 | 0.058 (2) | 0.063 (2) | 0.0365 (16) | 0.0073 (16) | 0.0130 (14) | 0.0039 (15) |
C2 | 0.066 (2) | 0.0456 (18) | 0.062 (2) | −0.0010 (16) | 0.0062 (18) | −0.0170 (16) |
C3 | 0.056 (2) | 0.063 (2) | 0.071 (2) | −0.0100 (17) | −0.0033 (18) | −0.0028 (19) |
C4 | 0.067 (2) | 0.057 (2) | 0.063 (2) | 0.0246 (17) | 0.0194 (18) | 0.0080 (18) |
C5 | 0.071 (2) | 0.066 (2) | 0.076 (2) | 0.0059 (18) | 0.032 (2) | −0.016 (2) |
C6 | 0.0563 (19) | 0.0502 (19) | 0.067 (2) | 0.0073 (16) | 0.0069 (16) | −0.0057 (17) |
C7 | 0.0529 (17) | 0.0482 (17) | 0.0347 (15) | 0.0020 (13) | 0.0110 (13) | −0.0028 (13) |
C8 | 0.0483 (17) | 0.0397 (16) | 0.0513 (17) | 0.0009 (13) | 0.0130 (14) | 0.0051 (13) |
C9 | 0.0566 (18) | 0.0418 (17) | 0.0519 (18) | 0.0098 (14) | 0.0037 (15) | 0.0119 (14) |
S1 | 0.0619 (5) | 0.0638 (5) | 0.0379 (4) | 0.0063 (4) | 0.0039 (4) | −0.0014 (4) |
C10 | 0.0530 (18) | 0.0535 (19) | 0.0436 (17) | 0.0054 (15) | 0.0000 (14) | 0.0027 (14) |
C11 | 0.059 (2) | 0.055 (2) | 0.067 (2) | 0.0177 (16) | 0.0182 (17) | 0.0049 (17) |
C12 | 0.060 (2) | 0.0515 (19) | 0.056 (2) | −0.0008 (15) | 0.0154 (16) | 0.0025 (15) |
C13 | 0.0506 (19) | 0.061 (2) | 0.075 (2) | −0.0112 (16) | 0.0112 (17) | 0.0335 (18) |
C14 | 0.0406 (17) | 0.064 (2) | 0.063 (2) | 0.0054 (14) | 0.0052 (15) | 0.0018 (17) |
C15 | 0.0542 (18) | 0.0412 (16) | 0.0512 (17) | 0.0069 (14) | 0.0153 (15) | −0.0062 (14) |
C16 | 0.0500 (18) | 0.074 (2) | 0.0516 (19) | 0.0026 (16) | 0.0178 (15) | 0.0031 (17) |
C17 | 0.078 (2) | 0.062 (2) | 0.062 (2) | 0.0046 (18) | 0.0274 (19) | 0.0238 (18) |
Cl1 | 0.0674 (5) | 0.0663 (6) | 0.0663 (5) | 0.0288 (4) | 0.0256 (4) | 0.0153 (4) |
N1 | 0.0506 (16) | 0.0581 (17) | 0.0463 (15) | −0.0042 (12) | 0.0104 (12) | −0.0016 (13) |
N2 | 0.0575 (16) | 0.0523 (16) | 0.0432 (15) | 0.0045 (12) | 0.0137 (12) | 0.0031 (12) |
O1 | 0.0707 (15) | 0.0666 (16) | 0.0556 (14) | −0.0212 (12) | 0.0198 (12) | −0.0160 (12) |
O2 | 0.0584 (14) | 0.0594 (14) | 0.0568 (14) | 0.0008 (11) | 0.0193 (11) | 0.0104 (11) |
C1—C2 | 1.370 (5) | C10—N1 | 1.363 (4) |
C1—C6 | 1.405 (5) | C11—C12 | 1.389 (5) |
C1—C7 | 1.587 (4) | C11—H11 | 0.9300 |
C2—C3 | 1.398 (5) | C12—N2 | 1.456 (4) |
C2—H2 | 0.9300 | C12—C13 | 1.505 (5) |
C3—C4 | 1.401 (5) | C13—H13A | 0.9600 |
C3—H3 | 0.9300 | C13—H13B | 0.9600 |
C4—C5 | 1.389 (5) | C13—H13C | 0.9600 |
C4—Cl1 | 1.791 (3) | C14—H14A | 0.9600 |
C5—C6 | 1.375 (5) | C14—H14B | 0.9600 |
C5—H5 | 0.9300 | C14—H14C | 0.9600 |
C6—H6 | 0.9300 | C15—O1 | 1.225 (4) |
C7—N2 | 1.524 (4) | C15—O2 | 1.376 (4) |
C7—C8 | 1.534 (4) | C16—O2 | 1.489 (4) |
C7—H7 | 0.9800 | C16—C17 | 1.516 (5) |
C8—C9 | 1.398 (4) | C16—H16A | 0.9700 |
C8—C15 | 1.492 (4) | C16—H16B | 0.9700 |
C9—N1 | 1.471 (4) | C17—H17C | 0.9600 |
C9—C14 | 1.473 (5) | C17—H17D | 0.9600 |
S1—C10 | 1.766 (3) | C17—H17E | 0.9600 |
S1—C11 | 1.792 (4) | N1—H1A | 0.86 (4) |
C10—N2 | 1.355 (4) | ||
C2—C1—C6 | 120.5 (3) | C11—C12—N2 | 111.7 (3) |
C2—C1—C7 | 119.5 (3) | C11—C12—C13 | 127.5 (3) |
C6—C1—C7 | 120.0 (3) | N2—C12—C13 | 120.8 (3) |
C1—C2—C3 | 121.0 (3) | C12—C13—H13A | 109.5 |
C1—C2—H2 | 119.5 | C12—C13—H13B | 109.5 |
C3—C2—H2 | 119.5 | H13A—C13—H13B | 109.5 |
C2—C3—C4 | 117.8 (3) | C12—C13—H13C | 109.5 |
C2—C3—H3 | 121.1 | H13A—C13—H13C | 109.5 |
C4—C3—H3 | 121.1 | H13B—C13—H13C | 109.5 |
C5—C4—C3 | 121.3 (3) | C9—C14—H14A | 109.5 |
C5—C4—Cl1 | 117.9 (3) | C9—C14—H14B | 109.5 |
C3—C4—Cl1 | 120.8 (3) | H14A—C14—H14B | 109.5 |
C6—C5—C4 | 119.8 (3) | C9—C14—H14C | 109.5 |
C6—C5—H5 | 120.1 | H14A—C14—H14C | 109.5 |
C4—C5—H5 | 120.1 | H14B—C14—H14C | 109.5 |
C5—C6—C1 | 119.5 (3) | O1—C15—O2 | 121.9 (3) |
C5—C6—H6 | 120.3 | O1—C15—C8 | 122.6 (3) |
C1—C6—H6 | 120.3 | O2—C15—C8 | 115.4 (3) |
N2—C7—C8 | 107.9 (2) | O2—C16—C17 | 109.9 (3) |
N2—C7—C1 | 108.8 (2) | O2—C16—H16A | 109.7 |
C8—C7—C1 | 111.9 (2) | C17—C16—H16A | 109.7 |
N2—C7—H7 | 109.4 | O2—C16—H16B | 109.7 |
C8—C7—H7 | 109.4 | C17—C16—H16B | 109.7 |
C1—C7—H7 | 109.4 | H16A—C16—H16B | 108.2 |
C9—C8—C15 | 123.9 (3) | C16—C17—H17C | 109.5 |
C9—C8—C7 | 124.8 (3) | C16—C17—H17D | 109.5 |
C15—C8—C7 | 111.2 (3) | H17C—C17—H17D | 109.5 |
C8—C9—N1 | 116.1 (3) | C16—C17—H17E | 109.5 |
C8—C9—C14 | 134.5 (3) | H17C—C17—H17E | 109.5 |
N1—C9—C14 | 109.4 (3) | H17D—C17—H17E | 109.5 |
C10—S1—C11 | 90.78 (17) | C10—N1—C9 | 121.5 (3) |
N2—C10—N1 | 121.7 (3) | C10—N1—H1A | 119 (2) |
N2—C10—S1 | 111.8 (2) | C9—N1—H1A | 119 (2) |
N1—C10—S1 | 126.5 (2) | C10—N2—C12 | 114.4 (3) |
C12—C11—S1 | 111.1 (3) | C10—N2—C7 | 124.0 (3) |
C12—C11—H11 | 124.4 | C12—N2—C7 | 121.6 (3) |
S1—C11—H11 | 124.4 | C15—O2—C16 | 115.8 (2) |
Experimental details
Crystal data | |
Chemical formula | C17H18ClN2O2S+·Br− |
Mr | 429.75 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 291 |
a, b, c (Å) | 25.457 (2), 11.697 (2), 14.231 (3) |
β (°) | 106.8080 (16) |
V (Å3) | 4056.5 (12) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 2.27 |
Crystal size (mm) | 0.30 × 0.26 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.505, 0.584 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10641, 3986, 2937 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.094, 1.04 |
No. of reflections | 3986 |
No. of parameters | 223 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.26, −0.29 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Bruker, 2000).
A number of thiazolo[3,2-a]pyrimidine derivatives have been reported in the literature. These heterocyclic compounds are pharmacologically interesting systems with remarkable biological activities such as anti-inflammatory, anti-cancer and anti-microbial properties (Tozkoparan et al., 1998; Holla et al., 2004; Sayed et al., 2006).
The structure of the newly synthesized compound, (I), was confirmed by its elemental analysis, and by IR, NMR and mass spectroscopic studies. The crystallographic analysis (Fig. 1) shows the aryl and oxazolidine rings to be essentially co-planar