In the title compound, C
17H
13Cl
2NOS, the heterocyclic five-membered ring is essentially planar. The molecules in the crystal structure are stabilized by intermolecular C—H
π interactions and weak intramolecular C—H
Cl hydrogen-bond interactions.
Supporting information
CCDC reference: 277768
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- R factor = 0.040
- wR factor = 0.091
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16 .. CG1 .. 3.19 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13 .. CG2 .. 3.10 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. CG3 .. 2.91 Ang.
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 26.40
From the CIF: _reflns_number_total 3235
Count of symmetry unique reflns 1797
Completeness (_total/calc) 180.02%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1438
Fraction of Friedel pairs measured 0.800
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 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
1 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
(
Z)-1-(2,5-dichlorophenyl)-2-(3-phenylthiazolidin-2-ylidene)ethanone
top
Crystal data top
C17H13Cl2NOS | F(000) = 2880 |
Mr = 350.24 | Dx = 1.454 Mg m−3 |
Orthorhombic, Fdd2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: F 2 -2d | Cell parameters from 2162 reflections |
a = 26.088 (4) Å | θ = 3.2–23.1° |
b = 37.204 (6) Å | µ = 0.54 mm−1 |
c = 6.5952 (11) Å | T = 294 K |
V = 6401.1 (19) Å3 | Block, yellow |
Z = 16 | 0.42 × 0.28 × 0.24 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3235 independent reflections |
Radiation source: fine-focus sealed tube | 2178 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
φ and ω scans | θmax = 26.4°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −32→32 |
Tmin = 0.790, Tmax = 0.879 | k = −46→23 |
8964 measured reflections | l = −8→8 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.092 | w = 1/[σ2(Fo2) + (0.0387P)2 + 1.9653P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3235 reflections | Δρmax = 0.23 e Å−3 |
199 parameters | Δρmin = −0.24 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1443 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (8) |
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 | 0.02421 (3) | 0.24054 (2) | 0.24524 (14) | 0.0435 (2) | |
Cl1 | 0.15863 (4) | 0.26073 (3) | 0.89450 (13) | 0.0562 (3) | |
Cl2 | 0.28175 (4) | 0.34881 (3) | 0.2596 (2) | 0.0786 (4) | |
N1 | 0.05074 (10) | 0.18636 (7) | 0.4641 (4) | 0.0374 (7) | |
O1 | 0.09828 (9) | 0.29119 (6) | 0.3179 (4) | 0.0482 (7) | |
C1 | −0.01887 (14) | 0.20255 (9) | 0.2527 (7) | 0.0599 (11) | |
H1A | −0.0518 | 0.2099 | 0.3067 | 0.072* | |
H1B | −0.0241 | 0.1933 | 0.1167 | 0.072* | |
C2 | 0.00299 (17) | 0.17495 (12) | 0.3793 (8) | 0.0786 (14) | |
H2A | −0.0207 | 0.1692 | 0.4879 | 0.094* | |
H2B | 0.0083 | 0.1534 | 0.2995 | 0.094* | |
C3 | 0.06673 (12) | 0.21970 (8) | 0.4100 (5) | 0.0330 (8) | |
C4 | 0.11136 (12) | 0.23544 (8) | 0.4754 (5) | 0.0368 (8) | |
H4 | 0.1339 | 0.2220 | 0.5540 | 0.044* | |
C5 | 0.12427 (13) | 0.27151 (8) | 0.4272 (5) | 0.0343 (8) | |
C6 | 0.17417 (12) | 0.28681 (8) | 0.5084 (5) | 0.0351 (8) | |
C7 | 0.19281 (13) | 0.28323 (9) | 0.7060 (5) | 0.0396 (9) | |
C8 | 0.23825 (14) | 0.29949 (9) | 0.7650 (7) | 0.0500 (10) | |
H8 | 0.2499 | 0.2970 | 0.8975 | 0.060* | |
C9 | 0.26605 (14) | 0.31930 (10) | 0.6273 (6) | 0.0505 (10) | |
H9 | 0.2969 | 0.3299 | 0.6652 | 0.061* | |
C10 | 0.24775 (14) | 0.32318 (10) | 0.4339 (6) | 0.0478 (10) | |
C11 | 0.20267 (13) | 0.30727 (9) | 0.3751 (6) | 0.0414 (8) | |
H11 | 0.1911 | 0.3103 | 0.2428 | 0.050* | |
C12 | 0.07613 (12) | 0.16530 (9) | 0.6145 (5) | 0.0357 (8) | |
C13 | 0.09360 (13) | 0.13134 (9) | 0.5668 (6) | 0.0442 (9) | |
H13 | 0.0893 | 0.1222 | 0.4367 | 0.053* | |
C14 | 0.11777 (14) | 0.11097 (9) | 0.7159 (7) | 0.0553 (11) | |
H14 | 0.1294 | 0.0880 | 0.6853 | 0.066* | |
C15 | 0.12459 (15) | 0.12443 (11) | 0.9067 (7) | 0.0561 (11) | |
H15 | 0.1411 | 0.1107 | 1.0049 | 0.067* | |
C16 | 0.10716 (14) | 0.15812 (10) | 0.9535 (6) | 0.0518 (10) | |
H16 | 0.1121 | 0.1674 | 1.0830 | 0.062* | |
C17 | 0.08226 (14) | 0.17828 (9) | 0.8082 (5) | 0.0431 (9) | |
H17 | 0.0695 | 0.2009 | 0.8415 | 0.052* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0412 (5) | 0.0441 (5) | 0.0453 (5) | 0.0010 (4) | −0.0080 (5) | 0.0076 (5) |
Cl1 | 0.0680 (7) | 0.0597 (6) | 0.0409 (5) | −0.0075 (5) | 0.0025 (5) | 0.0014 (5) |
Cl2 | 0.0672 (7) | 0.0862 (8) | 0.0824 (8) | −0.0363 (6) | 0.0222 (7) | −0.0054 (7) |
N1 | 0.0378 (16) | 0.0313 (15) | 0.0433 (17) | −0.0053 (12) | −0.0103 (14) | 0.0057 (13) |
O1 | 0.0446 (15) | 0.0400 (14) | 0.0602 (17) | −0.0044 (12) | −0.0076 (13) | 0.0173 (13) |
C1 | 0.050 (2) | 0.055 (2) | 0.075 (3) | −0.0073 (19) | −0.025 (2) | 0.012 (2) |
C2 | 0.066 (3) | 0.064 (3) | 0.106 (4) | −0.028 (2) | −0.048 (3) | 0.030 (3) |
C3 | 0.0331 (19) | 0.0314 (18) | 0.0345 (18) | 0.0018 (15) | 0.0048 (16) | −0.0010 (16) |
C4 | 0.0350 (18) | 0.0323 (18) | 0.043 (2) | 0.0031 (15) | −0.0021 (16) | 0.0062 (18) |
C5 | 0.0350 (18) | 0.0331 (19) | 0.035 (2) | −0.0018 (15) | 0.0069 (16) | −0.0022 (16) |
C6 | 0.0355 (18) | 0.0269 (18) | 0.043 (2) | 0.0012 (14) | 0.0013 (17) | −0.0042 (17) |
C7 | 0.045 (2) | 0.0316 (19) | 0.043 (2) | 0.0036 (16) | 0.0022 (17) | −0.0036 (16) |
C8 | 0.050 (2) | 0.047 (2) | 0.052 (2) | 0.0050 (19) | −0.015 (2) | −0.011 (2) |
C9 | 0.038 (2) | 0.046 (2) | 0.068 (3) | −0.0047 (18) | −0.002 (2) | −0.013 (2) |
C10 | 0.039 (2) | 0.045 (2) | 0.059 (3) | −0.0071 (18) | 0.0123 (19) | −0.007 (2) |
C11 | 0.042 (2) | 0.0368 (19) | 0.046 (2) | −0.0038 (16) | 0.0014 (18) | −0.0018 (18) |
C12 | 0.0313 (18) | 0.0308 (19) | 0.045 (2) | −0.0017 (15) | −0.0017 (17) | 0.0066 (17) |
C13 | 0.047 (2) | 0.029 (2) | 0.056 (2) | −0.0037 (16) | −0.0060 (18) | −0.0011 (17) |
C14 | 0.045 (2) | 0.0275 (19) | 0.094 (4) | 0.0036 (17) | −0.006 (2) | 0.001 (2) |
C15 | 0.043 (2) | 0.048 (2) | 0.077 (3) | −0.0068 (18) | −0.017 (2) | 0.026 (2) |
C16 | 0.059 (3) | 0.048 (2) | 0.049 (2) | −0.0035 (19) | −0.006 (2) | 0.008 (2) |
C17 | 0.051 (2) | 0.0338 (19) | 0.045 (2) | 0.0049 (17) | −0.0016 (18) | 0.0037 (19) |
Geometric parameters (Å, º) top
S1—C3 | 1.736 (3) | C7—C8 | 1.387 (5) |
S1—C1 | 1.806 (3) | C8—C9 | 1.376 (5) |
Cl1—C7 | 1.744 (3) | C8—H8 | 0.9300 |
Cl2—C10 | 1.737 (4) | C9—C10 | 1.370 (5) |
N1—C3 | 1.356 (4) | C9—H9 | 0.9300 |
N1—C12 | 1.427 (4) | C10—C11 | 1.372 (5) |
N1—C2 | 1.430 (4) | C11—H11 | 0.9300 |
O1—C5 | 1.231 (4) | C12—C17 | 1.375 (5) |
C1—C2 | 1.441 (5) | C12—C13 | 1.379 (5) |
C1—H1A | 0.9700 | C13—C14 | 1.393 (5) |
C1—H1B | 0.9700 | C13—H13 | 0.9300 |
C2—H2A | 0.9700 | C14—C15 | 1.366 (5) |
C2—H2B | 0.9700 | C14—H14 | 0.9300 |
C3—C4 | 1.373 (4) | C15—C16 | 1.368 (5) |
C4—C5 | 1.419 (4) | C15—H15 | 0.9300 |
C4—H4 | 0.9300 | C16—C17 | 1.380 (5) |
C5—C6 | 1.518 (4) | C16—H16 | 0.9300 |
C6—C11 | 1.380 (4) | C17—H17 | 0.9300 |
C6—C7 | 1.398 (5) | | |
| | | |
C3—S1—C1 | 91.78 (17) | C9—C8—C7 | 120.0 (4) |
C3—N1—C12 | 122.8 (3) | C9—C8—H8 | 120.0 |
C3—N1—C2 | 115.9 (3) | C7—C8—H8 | 120.0 |
C12—N1—C2 | 120.9 (3) | C10—C9—C8 | 119.2 (4) |
C2—C1—S1 | 109.1 (3) | C10—C9—H9 | 120.4 |
C2—C1—H1A | 109.9 | C8—C9—H9 | 120.4 |
S1—C1—H1A | 109.9 | C9—C10—C11 | 121.1 (4) |
C2—C1—H1B | 109.9 | C9—C10—Cl2 | 119.7 (3) |
S1—C1—H1B | 109.9 | C11—C10—Cl2 | 119.2 (3) |
H1A—C1—H1B | 108.3 | C10—C11—C6 | 121.3 (3) |
N1—C2—C1 | 111.1 (3) | C10—C11—H11 | 119.4 |
N1—C2—H2A | 109.4 | C6—C11—H11 | 119.4 |
C1—C2—H2A | 109.4 | C17—C12—C13 | 119.7 (3) |
N1—C2—H2B | 109.4 | C17—C12—N1 | 120.4 (3) |
C1—C2—H2B | 109.4 | C13—C12—N1 | 119.9 (3) |
H2A—C2—H2B | 108.0 | C12—C13—C14 | 119.1 (3) |
N1—C3—C4 | 124.6 (3) | C12—C13—H13 | 120.4 |
N1—C3—S1 | 112.1 (2) | C14—C13—H13 | 120.4 |
C4—C3—S1 | 123.2 (2) | C15—C14—C13 | 120.7 (3) |
C3—C4—C5 | 122.3 (3) | C15—C14—H14 | 119.7 |
C3—C4—H4 | 118.9 | C13—C14—H14 | 119.7 |
C5—C4—H4 | 118.9 | C14—C15—C16 | 120.0 (4) |
O1—C5—C4 | 124.2 (3) | C14—C15—H15 | 120.0 |
O1—C5—C6 | 117.1 (3) | C16—C15—H15 | 120.0 |
C4—C5—C6 | 118.6 (3) | C15—C16—C17 | 119.9 (4) |
C11—C6—C7 | 117.3 (3) | C15—C16—H16 | 120.1 |
C11—C6—C5 | 116.4 (3) | C17—C16—H16 | 120.1 |
C7—C6—C5 | 126.2 (3) | C12—C17—C16 | 120.6 (3) |
C8—C7—C6 | 121.2 (3) | C12—C17—H17 | 119.7 |
C8—C7—Cl1 | 116.5 (3) | C16—C17—H17 | 119.7 |
C6—C7—Cl1 | 122.2 (3) | | |
| | | |
C3—S1—C1—C2 | −1.7 (4) | C6—C7—C8—C9 | −0.6 (5) |
C3—N1—C2—C1 | −0.9 (5) | Cl1—C7—C8—C9 | −176.7 (3) |
C12—N1—C2—C1 | 172.0 (4) | C7—C8—C9—C10 | 1.2 (5) |
S1—C1—C2—N1 | 1.7 (5) | C8—C9—C10—C11 | −0.9 (6) |
C12—N1—C3—C4 | 7.2 (5) | C8—C9—C10—Cl2 | 178.8 (3) |
C2—N1—C3—C4 | 179.9 (3) | C9—C10—C11—C6 | 0.0 (6) |
C12—N1—C3—S1 | −173.2 (2) | Cl2—C10—C11—C6 | −179.7 (3) |
C2—N1—C3—S1 | −0.5 (4) | C7—C6—C11—C10 | 0.6 (5) |
C1—S1—C3—N1 | 1.3 (3) | C5—C6—C11—C10 | 178.3 (3) |
C1—S1—C3—C4 | −179.1 (3) | C3—N1—C12—C17 | 57.7 (4) |
N1—C3—C4—C5 | −174.8 (3) | C2—N1—C12—C17 | −114.7 (4) |
S1—C3—C4—C5 | 5.7 (5) | C3—N1—C12—C13 | −123.9 (3) |
C3—C4—C5—O1 | −3.1 (5) | C2—N1—C12—C13 | 63.8 (5) |
C3—C4—C5—C6 | 179.3 (3) | C17—C12—C13—C14 | −0.8 (5) |
O1—C5—C6—C11 | −40.4 (4) | N1—C12—C13—C14 | −179.3 (3) |
C4—C5—C6—C11 | 137.4 (3) | C12—C13—C14—C15 | −0.6 (5) |
O1—C5—C6—C7 | 137.0 (3) | C13—C14—C15—C16 | 0.6 (6) |
C4—C5—C6—C7 | −45.1 (5) | C14—C15—C16—C17 | 0.6 (6) |
C11—C6—C7—C8 | −0.3 (5) | C13—C12—C17—C16 | 2.1 (5) |
C5—C6—C7—C8 | −177.7 (3) | N1—C12—C17—C16 | −179.5 (3) |
C11—C6—C7—Cl1 | 175.6 (2) | C15—C16—C17—C12 | −2.0 (5) |
C5—C6—C7—Cl1 | −1.8 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···Cl1 | 0.93 | 2.74 | 3.169 (5) | 109 |
C16—H16···Cg1i | 0.93 | 3.19 | 3.800 (4) | 125 |
C13—H13···Cg2ii | 0.93 | 3.10 | 3.727 (1) | 127 |
C9—H9···Cg3iii | 0.93 | 2.91 | 3.838 (2) | 173 |
Symmetry codes: (i) x, y, z+1; (ii) x+1/4, −y−1/4, z−1/4; (iii) x−1, y, z. |