In the title molecule, C
20H
12ClNO
4S, the benzopyran ring system and the thiazolidine ring are planar. The dihedral angle between the chlorobenzyl and thiazolidine rings is 74.42 (8)°. The crystal structure is stabilized by intermolecular C—H
O hydrogen bonds.
Supporting information
CCDC reference: 270260
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.048
- wR factor = 0.125
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
Tmin and Tmax reported: 0.388 0.595
Tmin and Tmax expected: 0.342 0.602
RR = 1.150
Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.15
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16 .. O1 .. 2.89 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19 .. O4 .. 2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H20 .. O4 .. 2.83 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C20H12ClNO4S | Z = 2 |
Mr = 398.82 | F(000) = 408 |
Triclinic, P1 | Dx = 1.554 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54180 Å |
a = 8.7819 (8) Å | Cell parameters from 25 reflections |
b = 10.2641 (7) Å | θ = 19.2–42.6° |
c = 10.4074 (12) Å | µ = 3.38 mm−1 |
α = 112.034 (8)° | T = 293 K |
β = 98.297 (8)° | Prism, colourless |
γ = 94.009 (7)° | 0.48 × 0.3 × 0.15 mm |
V = 852.58 (14) Å3 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.015 |
non–profiled ω scans | θmax = 74.2°, θmin = 4.7° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→10 |
Tmin = 0.388, Tmax = 0.596 | k = −12→12 |
3583 measured reflections | l = −12→12 |
3365 independent reflections | 3 standard reflections every 120 min |
2864 reflections with I > 2σ(I) | intensity decay: 2% |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0554P)2 + 0.3299P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.048 | (Δ/σ)max < 0.001 |
wR(F2) = 0.125 | Δρmax = 0.62 e Å−3 |
S = 1.2 | Δρmin = −0.41 e Å−3 |
3365 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
245 parameters | Extinction coefficient: 0.0049 (6) |
0 restraints | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.33256 (8) | 0.41593 (8) | 0.54763 (8) | 0.0569 (2) | |
S1 | 0.06445 (7) | 0.82037 (6) | −0.01058 (6) | 0.03906 (18) | |
O1 | −0.1421 (2) | 0.6407 (2) | 0.02151 (19) | 0.0534 (5) | |
O2 | 0.1718 (2) | 0.99414 (19) | 0.39384 (18) | 0.0521 (5) | |
O3 | 0.5229 (2) | 1.31552 (19) | 0.1013 (2) | 0.0541 (5) | |
O4 | 0.2415 (3) | 0.9445 (2) | −0.1339 (2) | 0.0647 (6) | |
N1 | 0.0039 (2) | 0.8102 (2) | 0.2238 (2) | 0.0365 (4) | |
C1 | −0.0423 (3) | 0.7417 (2) | 0.0795 (2) | 0.0387 (5) | |
C2 | 0.1681 (3) | 0.9490 (2) | 0.1484 (2) | 0.0356 (5) | |
C3 | 0.1197 (3) | 0.9247 (2) | 0.2703 (2) | 0.0372 (5) | |
C4 | 0.2744 (3) | 1.0613 (2) | 0.1771 (2) | 0.0381 (5) | |
H4 | 0.3086 | 1.1125 | 0.2733 | 0.046* | |
C5 | 0.3476 (3) | 1.1203 (2) | 0.0910 (2) | 0.0382 (5) | |
C6 | 0.3250 (3) | 1.0557 (2) | −0.0632 (3) | 0.0402 (5) | |
C7 | 0.4125 (3) | 1.1350 (2) | −0.1272 (3) | 0.0399 (5) | |
C8 | 0.5073 (3) | 1.2606 (3) | −0.0437 (3) | 0.0440 (6) | |
C9 | 0.4441 (3) | 1.2438 (3) | 0.1596 (3) | 0.0468 (6) | |
H9 | 0.4567 | 1.2826 | 0.2574 | 0.056* | |
C10 | 0.4018 (3) | 1.0867 (3) | −0.2732 (3) | 0.0467 (6) | |
H10 | 0.3391 | 1.0023 | −0.3318 | 0.056* | |
C11 | 0.4836 (3) | 1.1633 (3) | −0.3308 (3) | 0.0545 (7) | |
H11 | 0.4758 | 1.1309 | −0.4281 | 0.065* | |
C12 | 0.5779 (4) | 1.2890 (3) | −0.2438 (3) | 0.0582 (7) | |
H12 | 0.6328 | 1.34 | −0.2837 | 0.07* | |
C13 | 0.5914 (3) | 1.3391 (3) | −0.1003 (3) | 0.0546 (7) | |
H13 | 0.6549 | 1.4232 | −0.0423 | 0.065* | |
C14 | −0.0660 (3) | 0.7650 (3) | 0.3232 (3) | 0.0414 (5) | |
H14A | −0.1663 | 0.7089 | 0.2758 | 0.05* | |
H14B | −0.0828 | 0.8481 | 0.4012 | 0.05* | |
C15 | 0.0355 (3) | 0.6785 (2) | 0.3800 (2) | 0.0368 (5) | |
C16 | 0.0630 (3) | 0.5469 (3) | 0.2911 (3) | 0.0462 (6) | |
H16 | 0.019 | 0.5122 | 0.1958 | 0.055* | |
C17 | 0.1548 (3) | 0.4661 (3) | 0.3412 (3) | 0.0474 (6) | |
H17 | 0.1733 | 0.378 | 0.2804 | 0.057* | |
C18 | 0.2185 (3) | 0.5180 (3) | 0.4828 (3) | 0.0409 (5) | |
C19 | 0.1920 (3) | 0.6470 (3) | 0.5739 (3) | 0.0488 (6) | |
H19 | 0.2345 | 0.6802 | 0.6694 | 0.059* | |
C20 | 0.1005 (3) | 0.7279 (3) | 0.5214 (3) | 0.0449 (6) | |
H20 | 0.0829 | 0.8163 | 0.5824 | 0.054* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0520 (4) | 0.0640 (4) | 0.0667 (4) | 0.0136 (3) | 0.0065 (3) | 0.0395 (4) |
S1 | 0.0444 (3) | 0.0391 (3) | 0.0314 (3) | −0.0012 (2) | 0.0041 (2) | 0.0135 (2) |
O1 | 0.0553 (11) | 0.0519 (11) | 0.0463 (10) | −0.0121 (9) | 0.0067 (8) | 0.0159 (8) |
O2 | 0.0634 (12) | 0.0528 (10) | 0.0318 (9) | −0.0034 (9) | 0.0071 (8) | 0.0096 (8) |
O3 | 0.0553 (11) | 0.0442 (10) | 0.0543 (11) | −0.0117 (8) | 0.0076 (9) | 0.0136 (8) |
O4 | 0.0834 (15) | 0.0546 (11) | 0.0415 (10) | −0.0250 (11) | 0.0154 (10) | 0.0071 (9) |
N1 | 0.0420 (10) | 0.0362 (10) | 0.0343 (9) | 0.0062 (8) | 0.0094 (8) | 0.0160 (8) |
C1 | 0.0429 (13) | 0.0366 (12) | 0.0369 (12) | 0.0052 (10) | 0.0063 (10) | 0.0149 (10) |
C2 | 0.0404 (12) | 0.0332 (11) | 0.0329 (11) | 0.0078 (9) | 0.0054 (9) | 0.0125 (9) |
C3 | 0.0416 (12) | 0.0346 (11) | 0.0356 (11) | 0.0081 (9) | 0.0082 (10) | 0.0133 (9) |
C4 | 0.0410 (12) | 0.0366 (12) | 0.0342 (11) | 0.0059 (10) | 0.0048 (9) | 0.0116 (9) |
C5 | 0.0372 (12) | 0.0357 (11) | 0.0402 (12) | 0.0046 (9) | 0.0048 (10) | 0.0142 (10) |
C6 | 0.0413 (13) | 0.0357 (12) | 0.0426 (13) | 0.0029 (10) | 0.0096 (10) | 0.0139 (10) |
C7 | 0.0367 (12) | 0.0391 (12) | 0.0476 (13) | 0.0080 (10) | 0.0101 (10) | 0.0199 (10) |
C8 | 0.0408 (13) | 0.0421 (13) | 0.0517 (14) | 0.0052 (10) | 0.0092 (11) | 0.0211 (11) |
C9 | 0.0480 (14) | 0.0438 (13) | 0.0441 (14) | −0.0021 (11) | 0.0064 (11) | 0.0145 (11) |
C10 | 0.0463 (14) | 0.0499 (14) | 0.0478 (14) | 0.0082 (11) | 0.0098 (11) | 0.0226 (12) |
C11 | 0.0538 (16) | 0.0643 (17) | 0.0591 (17) | 0.0140 (14) | 0.0169 (13) | 0.0360 (14) |
C12 | 0.0515 (16) | 0.0666 (18) | 0.078 (2) | 0.0119 (14) | 0.0215 (15) | 0.0477 (17) |
C13 | 0.0449 (15) | 0.0489 (15) | 0.076 (2) | −0.0002 (12) | 0.0117 (14) | 0.0320 (14) |
C14 | 0.0444 (13) | 0.0442 (13) | 0.0425 (13) | 0.0105 (10) | 0.0162 (11) | 0.0208 (11) |
C15 | 0.0371 (12) | 0.0397 (12) | 0.0375 (11) | 0.0034 (9) | 0.0107 (9) | 0.0183 (10) |
C16 | 0.0558 (15) | 0.0445 (13) | 0.0353 (12) | 0.0089 (12) | 0.0037 (11) | 0.0134 (10) |
C17 | 0.0571 (16) | 0.0386 (13) | 0.0451 (14) | 0.0112 (11) | 0.0089 (12) | 0.0140 (11) |
C18 | 0.0361 (12) | 0.0446 (13) | 0.0479 (13) | 0.0025 (10) | 0.0065 (10) | 0.0257 (11) |
C19 | 0.0523 (15) | 0.0520 (15) | 0.0375 (13) | 0.0051 (12) | −0.0001 (11) | 0.0157 (11) |
C20 | 0.0500 (14) | 0.0426 (13) | 0.0383 (12) | 0.0071 (11) | 0.0078 (11) | 0.0115 (10) |
Geometric parameters (Å, º) top
Cl1—C18 | 1.743 (2) | C9—H9 | 0.93 |
S1—C2 | 1.752 (2) | C10—C11 | 1.376 (4) |
S1—C1 | 1.768 (2) | C10—H10 | 0.93 |
O1—C1 | 1.207 (3) | C11—C12 | 1.388 (4) |
O2—C3 | 1.211 (3) | C11—H11 | 0.93 |
O3—C9 | 1.332 (3) | C12—C13 | 1.368 (4) |
O3—C8 | 1.380 (3) | C12—H12 | 0.93 |
O4—C6 | 1.216 (3) | C13—H13 | 0.93 |
N1—C1 | 1.381 (3) | C14—C15 | 1.511 (3) |
N1—C3 | 1.383 (3) | C14—H14A | 0.97 |
N1—C14 | 1.472 (3) | C14—H14B | 0.97 |
C2—C4 | 1.341 (3) | C15—C20 | 1.381 (3) |
C2—C3 | 1.494 (3) | C15—C16 | 1.383 (3) |
C4—C5 | 1.450 (3) | C16—C17 | 1.381 (3) |
C4—H4 | 0.93 | C16—H16 | 0.93 |
C5—C9 | 1.353 (3) | C17—C18 | 1.378 (3) |
C5—C6 | 1.465 (3) | C17—H17 | 0.93 |
C6—C7 | 1.472 (3) | C18—C19 | 1.368 (4) |
C7—C8 | 1.382 (3) | C19—C20 | 1.393 (4) |
C7—C10 | 1.396 (4) | C19—H19 | 0.93 |
C8—C13 | 1.393 (4) | C20—H20 | 0.93 |
| | | |
C2—S1—C1 | 91.72 (11) | C7—C10—H10 | 119.8 |
C9—O3—C8 | 118.1 (2) | C10—C11—C12 | 120.1 (3) |
C1—N1—C3 | 116.26 (19) | C10—C11—H11 | 120 |
C1—N1—C14 | 122.18 (19) | C12—C11—H11 | 120 |
C3—N1—C14 | 121.56 (19) | C13—C12—C11 | 121.1 (3) |
O1—C1—N1 | 124.8 (2) | C13—C12—H12 | 119.4 |
O1—C1—S1 | 124.01 (19) | C11—C12—H12 | 119.4 |
N1—C1—S1 | 111.23 (17) | C12—C13—C8 | 118.1 (3) |
C4—C2—C3 | 117.6 (2) | C12—C13—H13 | 121 |
C4—C2—S1 | 132.29 (19) | C8—C13—H13 | 121 |
C3—C2—S1 | 110.10 (16) | N1—C14—C15 | 112.01 (19) |
O2—C3—N1 | 123.4 (2) | N1—C14—H14A | 109.2 |
O2—C3—C2 | 126.0 (2) | C15—C14—H14A | 109.2 |
N1—C3—C2 | 110.65 (19) | N1—C14—H14B | 109.2 |
C2—C4—C5 | 134.0 (2) | C15—C14—H14B | 109.2 |
C2—C4—H4 | 113 | H14A—C14—H14B | 107.9 |
C5—C4—H4 | 113 | C20—C15—C16 | 118.7 (2) |
C9—C5—C4 | 116.9 (2) | C20—C15—C14 | 120.9 (2) |
C9—C5—C6 | 118.3 (2) | C16—C15—C14 | 120.4 (2) |
C4—C5—C6 | 124.8 (2) | C17—C16—C15 | 121.2 (2) |
O4—C6—C5 | 123.1 (2) | C17—C16—H16 | 119.4 |
O4—C6—C7 | 122.0 (2) | C15—C16—H16 | 119.4 |
C5—C6—C7 | 114.9 (2) | C18—C17—C16 | 118.9 (2) |
C8—C7—C10 | 118.1 (2) | C18—C17—H17 | 120.5 |
C8—C7—C6 | 120.6 (2) | C16—C17—H17 | 120.5 |
C10—C7—C6 | 121.3 (2) | C19—C18—C17 | 121.3 (2) |
O3—C8—C7 | 121.4 (2) | C19—C18—Cl1 | 119.3 (2) |
O3—C8—C13 | 116.3 (2) | C17—C18—Cl1 | 119.4 (2) |
C7—C8—C13 | 122.3 (3) | C18—C19—C20 | 119.0 (2) |
O3—C9—C5 | 126.7 (2) | C18—C19—H19 | 120.5 |
O3—C9—H9 | 116.7 | C20—C19—H19 | 120.5 |
C5—C9—H9 | 116.7 | C15—C20—C19 | 120.8 (2) |
C11—C10—C7 | 120.3 (3) | C15—C20—H20 | 119.6 |
C11—C10—H10 | 119.8 | C19—C20—H20 | 119.6 |
| | | |
C3—N1—C1—O1 | −179.6 (2) | C9—O3—C8—C13 | 179.8 (2) |
C14—N1—C1—O1 | 0.2 (4) | C10—C7—C8—O3 | 179.6 (2) |
C3—N1—C1—S1 | 0.7 (3) | C6—C7—C8—O3 | 0.0 (4) |
C14—N1—C1—S1 | −179.58 (16) | C10—C7—C8—C13 | −0.1 (4) |
C2—S1—C1—O1 | 178.8 (2) | C6—C7—C8—C13 | −179.7 (2) |
C2—S1—C1—N1 | −1.40 (18) | C8—O3—C9—C5 | −0.2 (4) |
C1—S1—C2—C4 | −176.3 (2) | C4—C5—C9—O3 | 179.9 (2) |
C1—S1—C2—C3 | 1.72 (17) | C6—C5—C9—O3 | 0.1 (4) |
C1—N1—C3—O2 | −179.7 (2) | C8—C7—C10—C11 | −0.2 (4) |
C14—N1—C3—O2 | 0.6 (4) | C6—C7—C10—C11 | 179.4 (2) |
C1—N1—C3—C2 | 0.7 (3) | C7—C10—C11—C12 | 0.3 (4) |
C14—N1—C3—C2 | −179.11 (19) | C10—C11—C12—C13 | −0.1 (4) |
C4—C2—C3—O2 | −3.0 (4) | C11—C12—C13—C8 | −0.2 (4) |
S1—C2—C3—O2 | 178.6 (2) | O3—C8—C13—C12 | −179.4 (2) |
C4—C2—C3—N1 | 176.7 (2) | C7—C8—C13—C12 | 0.3 (4) |
S1—C2—C3—N1 | −1.7 (2) | C1—N1—C14—C15 | 100.8 (3) |
C3—C2—C4—C5 | −179.0 (2) | C3—N1—C14—C15 | −79.5 (3) |
S1—C2—C4—C5 | −1.1 (4) | N1—C14—C15—C20 | 115.3 (2) |
C2—C4—C5—C9 | 175.3 (3) | N1—C14—C15—C16 | −65.7 (3) |
C2—C4—C5—C6 | −4.9 (4) | C20—C15—C16—C17 | −0.6 (4) |
C9—C5—C6—O4 | 179.5 (3) | C14—C15—C16—C17 | −179.7 (2) |
C4—C5—C6—O4 | −0.2 (4) | C15—C16—C17—C18 | 0.5 (4) |
C9—C5—C6—C7 | 0.0 (3) | C16—C17—C18—C19 | 0.3 (4) |
C4—C5—C6—C7 | −179.7 (2) | C16—C17—C18—Cl1 | 179.2 (2) |
O4—C6—C7—C8 | −179.5 (3) | C17—C18—C19—C20 | −0.9 (4) |
C5—C6—C7—C8 | −0.1 (3) | Cl1—C18—C19—C20 | −179.9 (2) |
O4—C6—C7—C10 | 0.8 (4) | C16—C15—C20—C19 | 0.0 (4) |
C5—C6—C7—C10 | −179.7 (2) | C14—C15—C20—C19 | 179.0 (2) |
C9—O3—C8—C7 | 0.2 (4) | C18—C19—C20—C15 | 0.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O2 | 0.93 | 2.42 | 2.836 (3) | 107 |
C13—H13···O1i | 0.93 | 2.57 | 3.443 (4) | 157 |
C14—H14A···O1 | 0.97 | 2.52 | 2.864 (3) | 101 |
C14—H14B···O2ii | 0.97 | 2.42 | 3.361 (3) | 164 |
C16—H16···O1 | 0.93 | 2.89 | 3.585 (4) | 133 |
C19—H19···O4iii | 0.93 | 2.71 | 3.351 (3) | 127 |
C20—H20···O4iii | 0.93 | 2.83 | 3.420 (3) | 122 |
Symmetry codes: (i) x+1, y+1, z; (ii) −x, −y+2, −z+1; (iii) x, y, z+1. |