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The title compound, C
13H
10Cl
2N
2OS, was synthesized by mixing 2,4-dichlorobenzaldehyde, ethyl chloroacetate and tetrahydropyrimidine-2-thione in ethanol. The nearly planar thiazoline ring is fused to a dihydropyrimidine ring, which has a sofa conformation. The molecules are connected through weak C—H
N, C—H
O and C—H
Cl interactions.
Supporting information
CCDC reference: 248797
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.094
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
(2E)-2-(2,4-Dichlorobenzylidene)-6,7-dihydro-2
H-thiazolo[3,2-
a]pyrimidin- 3(5
H)-one
top
Crystal data top
C13H10Cl2N2OS | F(000) = 640 |
Mr = 313.19 | Dx = 1.555 Mg m−3 |
Monoclinic, P21/c | Melting point = 437–439 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 6.155 (2) Å | Cell parameters from 791 reflections |
b = 9.676 (4) Å | θ = 3.6–26.5° |
c = 22.507 (8) Å | µ = 0.63 mm−1 |
β = 93.543 (6)° | T = 293 K |
V = 1337.8 (8) Å3 | Block cut from needle, yellow |
Z = 4 | 0.28 × 0.26 × 0.20 mm |
Data collection top
Bruker SMART CCD diffractometer | 2841 independent reflections |
Radiation source: fine-focus sealed tube | 2191 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
φ and ω scans | θmax = 26.8°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −7→7 |
Tmin = 0.820, Tmax = 0.881 | k = −12→12 |
7749 measured reflections | l = −19→28 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0406P)2 + 0.4345P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.094 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.27 e Å−3 |
2841 reflections | Δρmin = −0.20 e Å−3 |
172 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 | Uiso*/Ueq | |
S1 | 0.14843 (10) | 0.52038 (6) | 0.40692 (2) | 0.04772 (18) | |
Cl1 | 0.90193 (10) | 0.15696 (7) | 0.41912 (3) | 0.0606 (2) | |
Cl2 | 0.59274 (12) | 0.05369 (7) | 0.63163 (3) | 0.0621 (2) | |
O1 | 0.5557 (3) | 0.48827 (17) | 0.28452 (7) | 0.0524 (4) | |
N1 | 0.2437 (3) | 0.60413 (17) | 0.30181 (7) | 0.0368 (4) | |
N2 | −0.0659 (3) | 0.7099 (2) | 0.34152 (9) | 0.0546 (5) | |
C1 | 0.2246 (4) | 0.6814 (2) | 0.24558 (9) | 0.0463 (5) | |
H1A | 0.2710 | 0.6240 | 0.2134 | 0.056* | |
H1B | 0.3169 | 0.7626 | 0.2484 | 0.056* | |
C2 | −0.0101 (4) | 0.7238 (3) | 0.23335 (11) | 0.0596 (7) | |
H2A | −0.0206 | 0.7872 | 0.1999 | 0.072* | |
H2B | −0.0967 | 0.6428 | 0.2225 | 0.072* | |
C3 | −0.1002 (4) | 0.7918 (3) | 0.28650 (11) | 0.0602 (7) | |
H3A | −0.0317 | 0.8814 | 0.2925 | 0.072* | |
H3B | −0.2551 | 0.8069 | 0.2785 | 0.072* | |
C4 | 0.0911 (3) | 0.6272 (2) | 0.34402 (9) | 0.0398 (5) | |
C5 | 0.4093 (3) | 0.5144 (2) | 0.31655 (9) | 0.0374 (5) | |
C6 | 0.3828 (3) | 0.4527 (2) | 0.37687 (9) | 0.0373 (5) | |
C7 | 0.5269 (4) | 0.3603 (2) | 0.39918 (9) | 0.0421 (5) | |
H7 | 0.6382 | 0.3396 | 0.3745 | 0.051* | |
C8 | 0.5390 (3) | 0.2865 (2) | 0.45577 (9) | 0.0392 (5) | |
C9 | 0.3883 (4) | 0.3042 (3) | 0.49957 (10) | 0.0513 (6) | |
H9 | 0.2746 | 0.3664 | 0.4923 | 0.062* | |
C10 | 0.4019 (4) | 0.2333 (3) | 0.55293 (10) | 0.0521 (6) | |
H10 | 0.2986 | 0.2470 | 0.5808 | 0.063* | |
C11 | 0.5701 (4) | 0.1424 (2) | 0.56408 (9) | 0.0443 (5) | |
C12 | 0.7249 (4) | 0.1199 (2) | 0.52314 (9) | 0.0464 (5) | |
H12 | 0.8388 | 0.0583 | 0.5312 | 0.056* | |
C13 | 0.7056 (3) | 0.1916 (2) | 0.46989 (9) | 0.0399 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0500 (3) | 0.0536 (4) | 0.0407 (3) | 0.0148 (3) | 0.0116 (2) | 0.0127 (3) |
Cl1 | 0.0598 (4) | 0.0708 (4) | 0.0525 (4) | 0.0284 (3) | 0.0149 (3) | 0.0150 (3) |
Cl2 | 0.0798 (5) | 0.0653 (4) | 0.0408 (3) | 0.0008 (3) | −0.0004 (3) | 0.0166 (3) |
O1 | 0.0554 (10) | 0.0594 (10) | 0.0437 (9) | 0.0180 (8) | 0.0137 (7) | 0.0023 (8) |
N1 | 0.0424 (10) | 0.0371 (9) | 0.0310 (9) | 0.0043 (8) | 0.0045 (7) | 0.0040 (7) |
N2 | 0.0526 (12) | 0.0621 (13) | 0.0501 (12) | 0.0193 (10) | 0.0114 (9) | 0.0140 (10) |
C1 | 0.0566 (14) | 0.0450 (13) | 0.0377 (12) | 0.0065 (11) | 0.0073 (10) | 0.0101 (10) |
C2 | 0.0679 (17) | 0.0675 (17) | 0.0426 (13) | 0.0175 (14) | −0.0022 (12) | 0.0132 (12) |
C3 | 0.0603 (16) | 0.0649 (17) | 0.0556 (15) | 0.0247 (13) | 0.0054 (12) | 0.0191 (13) |
C4 | 0.0430 (12) | 0.0403 (12) | 0.0365 (11) | 0.0037 (9) | 0.0052 (9) | 0.0066 (9) |
C5 | 0.0440 (12) | 0.0346 (11) | 0.0334 (11) | 0.0024 (9) | 0.0015 (9) | −0.0039 (8) |
C6 | 0.0437 (12) | 0.0364 (11) | 0.0317 (10) | 0.0040 (9) | 0.0021 (8) | −0.0021 (8) |
C7 | 0.0475 (13) | 0.0441 (12) | 0.0348 (11) | 0.0084 (10) | 0.0021 (9) | −0.0022 (9) |
C8 | 0.0440 (12) | 0.0407 (12) | 0.0325 (11) | 0.0068 (10) | −0.0015 (8) | −0.0013 (9) |
C9 | 0.0527 (14) | 0.0611 (15) | 0.0400 (12) | 0.0203 (12) | 0.0028 (10) | 0.0045 (11) |
C10 | 0.0582 (15) | 0.0619 (16) | 0.0370 (12) | 0.0090 (12) | 0.0095 (10) | 0.0007 (11) |
C11 | 0.0582 (14) | 0.0434 (12) | 0.0306 (11) | −0.0022 (11) | −0.0015 (9) | 0.0039 (9) |
C12 | 0.0543 (14) | 0.0435 (13) | 0.0408 (12) | 0.0125 (10) | −0.0026 (10) | 0.0056 (10) |
C13 | 0.0437 (12) | 0.0416 (12) | 0.0345 (11) | 0.0059 (9) | 0.0024 (9) | 0.0002 (9) |
Geometric parameters (Å, º) top
S1—C6 | 1.757 (2) | C3—H3A | 0.9700 |
S1—C4 | 1.771 (2) | C3—H3B | 0.9700 |
Cl1—C13 | 1.746 (2) | C5—C6 | 1.501 (3) |
Cl2—C11 | 1.744 (2) | C6—C7 | 1.336 (3) |
O1—C5 | 1.215 (2) | C7—C8 | 1.458 (3) |
N1—C5 | 1.364 (3) | C7—H7 | 0.9300 |
N1—C4 | 1.395 (3) | C8—C13 | 1.398 (3) |
N1—C1 | 1.468 (3) | C8—C9 | 1.405 (3) |
N2—C4 | 1.253 (3) | C9—C10 | 1.381 (3) |
N2—C3 | 1.474 (3) | C9—H9 | 0.9300 |
C1—C2 | 1.511 (3) | C10—C11 | 1.370 (3) |
C1—H1A | 0.9700 | C10—H10 | 0.9300 |
C1—H1B | 0.9700 | C11—C12 | 1.383 (3) |
C2—C3 | 1.501 (3) | C12—C13 | 1.383 (3) |
C2—H2A | 0.9700 | C12—H12 | 0.9300 |
C2—H2B | 0.9700 | | |
| | | |
C6—S1—C4 | 92.16 (10) | O1—C5—C6 | 125.44 (19) |
C5—N1—C4 | 117.44 (17) | N1—C5—C6 | 110.60 (17) |
C5—N1—C1 | 123.53 (17) | C7—C6—C5 | 119.97 (19) |
C4—N1—C1 | 118.96 (17) | C7—C6—S1 | 130.31 (17) |
C4—N2—C3 | 116.79 (19) | C5—C6—S1 | 109.72 (14) |
N1—C1—C2 | 108.66 (18) | C6—C7—C8 | 130.8 (2) |
N1—C1—H1A | 110.0 | C6—C7—H7 | 114.6 |
C2—C1—H1A | 110.0 | C8—C7—H7 | 114.6 |
N1—C1—H1B | 110.0 | C13—C8—C9 | 115.29 (19) |
C2—C1—H1B | 110.0 | C13—C8—C7 | 121.14 (19) |
H1A—C1—H1B | 108.3 | C9—C8—C7 | 123.56 (19) |
C3—C2—C1 | 111.7 (2) | C10—C9—C8 | 122.9 (2) |
C3—C2—H2A | 109.3 | C10—C9—H9 | 118.6 |
C1—C2—H2A | 109.3 | C8—C9—H9 | 118.6 |
C3—C2—H2B | 109.3 | C11—C10—C9 | 118.8 (2) |
C1—C2—H2B | 109.3 | C11—C10—H10 | 120.6 |
H2A—C2—H2B | 107.9 | C9—C10—H10 | 120.6 |
N2—C3—C2 | 113.1 (2) | C10—C11—C12 | 121.5 (2) |
N2—C3—H3A | 109.0 | C10—C11—Cl2 | 119.62 (17) |
C2—C3—H3A | 109.0 | C12—C11—Cl2 | 118.84 (17) |
N2—C3—H3B | 109.0 | C11—C12—C13 | 118.2 (2) |
C2—C3—H3B | 109.0 | C11—C12—H12 | 120.9 |
H3A—C3—H3B | 107.8 | C13—C12—H12 | 120.9 |
N2—C4—N1 | 128.45 (19) | C12—C13—C8 | 123.25 (19) |
N2—C4—S1 | 121.57 (16) | C12—C13—Cl1 | 116.43 (16) |
N1—C4—S1 | 109.98 (15) | C8—C13—Cl1 | 120.31 (16) |
O1—C5—N1 | 123.96 (19) | | |
| | | |
C5—N1—C1—C2 | 158.0 (2) | N1—C5—C6—S1 | −0.6 (2) |
C4—N1—C1—C2 | −25.0 (3) | C4—S1—C6—C7 | 179.3 (2) |
N1—C1—C2—C3 | 49.8 (3) | C4—S1—C6—C5 | −1.09 (16) |
C4—N2—C3—C2 | 25.2 (3) | C5—C6—C7—C8 | 179.7 (2) |
C1—C2—C3—N2 | −51.7 (3) | S1—C6—C7—C8 | −0.7 (4) |
C3—N2—C4—N1 | 1.8 (4) | C6—C7—C8—C13 | 179.3 (2) |
C3—N2—C4—S1 | −178.95 (18) | C6—C7—C8—C9 | −0.8 (4) |
C5—N1—C4—N2 | 175.8 (2) | C13—C8—C9—C10 | −0.1 (4) |
C1—N1—C4—N2 | −1.4 (4) | C7—C8—C9—C10 | 179.9 (2) |
C5—N1—C4—S1 | −3.6 (2) | C8—C9—C10—C11 | 0.5 (4) |
C1—N1—C4—S1 | 179.28 (16) | C9—C10—C11—C12 | −0.3 (4) |
C6—S1—C4—N2 | −176.9 (2) | C9—C10—C11—Cl2 | 179.04 (19) |
C6—S1—C4—N1 | 2.52 (16) | C10—C11—C12—C13 | −0.3 (4) |
C4—N1—C5—O1 | −177.9 (2) | Cl2—C11—C12—C13 | −179.63 (17) |
C1—N1—C5—O1 | −0.9 (3) | C11—C12—C13—C8 | 0.7 (3) |
C4—N1—C5—C6 | 2.7 (3) | C11—C12—C13—Cl1 | −178.75 (17) |
C1—N1—C5—C6 | 179.77 (18) | C9—C8—C13—C12 | −0.5 (3) |
O1—C5—C6—C7 | −0.4 (3) | C7—C8—C13—C12 | 179.5 (2) |
N1—C5—C6—C7 | 179.00 (19) | C9—C8—C13—Cl1 | 178.93 (17) |
O1—C5—C6—S1 | −179.99 (19) | C7—C8—C13—Cl1 | −1.1 (3) |
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