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In the title mol­ecule, C20H12ClNO4S, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805006252/ci6509sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805006252/ci6509Isup2.hkl
Contains datablock I

CCDC reference: 270260

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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).

(I) top
Crystal data top
C20H12ClNO4SZ = 2
Mr = 398.82F(000) = 408
Triclinic, P1Dx = 1.554 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54180 Å
a = 8.7819 (8) ÅCell parameters from 25 reflections
b = 10.2641 (7) Åθ = 19.2–42.6°
c = 10.4074 (12) ŵ = 3.38 mm1
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 scansθmax = 74.2°, θmin = 4.7°
Absorption correction: ψ scan
(North et al., 1968)
h = 010
Tmin = 0.388, Tmax = 0.596k = 1212
3583 measured reflectionsl = 1212
3365 independent reflections3 standard reflections every 120 min
2864 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2H-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) = 0.125Δρmax = 0.62 e Å3
S = 1.2Δρmin = 0.41 e Å3
3365 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
245 parametersExtinction 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
xyzUiso*/Ueq
Cl10.33256 (8)0.41593 (8)0.54763 (8)0.0569 (2)
S10.06445 (7)0.82037 (6)0.01058 (6)0.03906 (18)
O10.1421 (2)0.6407 (2)0.02151 (19)0.0534 (5)
O20.1718 (2)0.99414 (19)0.39384 (18)0.0521 (5)
O30.5229 (2)1.31552 (19)0.1013 (2)0.0541 (5)
O40.2415 (3)0.9445 (2)0.1339 (2)0.0647 (6)
N10.0039 (2)0.8102 (2)0.2238 (2)0.0365 (4)
C10.0423 (3)0.7417 (2)0.0795 (2)0.0387 (5)
C20.1681 (3)0.9490 (2)0.1484 (2)0.0356 (5)
C30.1197 (3)0.9247 (2)0.2703 (2)0.0372 (5)
C40.2744 (3)1.0613 (2)0.1771 (2)0.0381 (5)
H40.30861.11250.27330.046*
C50.3476 (3)1.1203 (2)0.0910 (2)0.0382 (5)
C60.3250 (3)1.0557 (2)0.0632 (3)0.0402 (5)
C70.4125 (3)1.1350 (2)0.1272 (3)0.0399 (5)
C80.5073 (3)1.2606 (3)0.0437 (3)0.0440 (6)
C90.4441 (3)1.2438 (3)0.1596 (3)0.0468 (6)
H90.45671.28260.25740.056*
C100.4018 (3)1.0867 (3)0.2732 (3)0.0467 (6)
H100.33911.00230.33180.056*
C110.4836 (3)1.1633 (3)0.3308 (3)0.0545 (7)
H110.47581.13090.42810.065*
C120.5779 (4)1.2890 (3)0.2438 (3)0.0582 (7)
H120.63281.340.28370.07*
C130.5914 (3)1.3391 (3)0.1003 (3)0.0546 (7)
H130.65491.42320.04230.065*
C140.0660 (3)0.7650 (3)0.3232 (3)0.0414 (5)
H14A0.16630.70890.27580.05*
H14B0.08280.84810.40120.05*
C150.0355 (3)0.6785 (2)0.3800 (2)0.0368 (5)
C160.0630 (3)0.5469 (3)0.2911 (3)0.0462 (6)
H160.0190.51220.19580.055*
C170.1548 (3)0.4661 (3)0.3412 (3)0.0474 (6)
H170.17330.3780.28040.057*
C180.2185 (3)0.5180 (3)0.4828 (3)0.0409 (5)
C190.1920 (3)0.6470 (3)0.5739 (3)0.0488 (6)
H190.23450.68020.66940.059*
C200.1005 (3)0.7279 (3)0.5214 (3)0.0449 (6)
H200.08290.81630.58240.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0520 (4)0.0640 (4)0.0667 (4)0.0136 (3)0.0065 (3)0.0395 (4)
S10.0444 (3)0.0391 (3)0.0314 (3)0.0012 (2)0.0041 (2)0.0135 (2)
O10.0553 (11)0.0519 (11)0.0463 (10)0.0121 (9)0.0067 (8)0.0159 (8)
O20.0634 (12)0.0528 (10)0.0318 (9)0.0034 (9)0.0071 (8)0.0096 (8)
O30.0553 (11)0.0442 (10)0.0543 (11)0.0117 (8)0.0076 (9)0.0136 (8)
O40.0834 (15)0.0546 (11)0.0415 (10)0.0250 (11)0.0154 (10)0.0071 (9)
N10.0420 (10)0.0362 (10)0.0343 (9)0.0062 (8)0.0094 (8)0.0160 (8)
C10.0429 (13)0.0366 (12)0.0369 (12)0.0052 (10)0.0063 (10)0.0149 (10)
C20.0404 (12)0.0332 (11)0.0329 (11)0.0078 (9)0.0054 (9)0.0125 (9)
C30.0416 (12)0.0346 (11)0.0356 (11)0.0081 (9)0.0082 (10)0.0133 (9)
C40.0410 (12)0.0366 (12)0.0342 (11)0.0059 (10)0.0048 (9)0.0116 (9)
C50.0372 (12)0.0357 (11)0.0402 (12)0.0046 (9)0.0048 (10)0.0142 (10)
C60.0413 (13)0.0357 (12)0.0426 (13)0.0029 (10)0.0096 (10)0.0139 (10)
C70.0367 (12)0.0391 (12)0.0476 (13)0.0080 (10)0.0101 (10)0.0199 (10)
C80.0408 (13)0.0421 (13)0.0517 (14)0.0052 (10)0.0092 (11)0.0211 (11)
C90.0480 (14)0.0438 (13)0.0441 (14)0.0021 (11)0.0064 (11)0.0145 (11)
C100.0463 (14)0.0499 (14)0.0478 (14)0.0082 (11)0.0098 (11)0.0226 (12)
C110.0538 (16)0.0643 (17)0.0591 (17)0.0140 (14)0.0169 (13)0.0360 (14)
C120.0515 (16)0.0666 (18)0.078 (2)0.0119 (14)0.0215 (15)0.0477 (17)
C130.0449 (15)0.0489 (15)0.076 (2)0.0002 (12)0.0117 (14)0.0320 (14)
C140.0444 (13)0.0442 (13)0.0425 (13)0.0105 (10)0.0162 (11)0.0208 (11)
C150.0371 (12)0.0397 (12)0.0375 (11)0.0034 (9)0.0107 (9)0.0183 (10)
C160.0558 (15)0.0445 (13)0.0353 (12)0.0089 (12)0.0037 (11)0.0134 (10)
C170.0571 (16)0.0386 (13)0.0451 (14)0.0112 (11)0.0089 (12)0.0140 (11)
C180.0361 (12)0.0446 (13)0.0479 (13)0.0025 (10)0.0065 (10)0.0257 (11)
C190.0523 (15)0.0520 (15)0.0375 (13)0.0051 (12)0.0001 (11)0.0157 (11)
C200.0500 (14)0.0426 (13)0.0383 (12)0.0071 (11)0.0078 (11)0.0115 (10)
Geometric parameters (Å, º) top
Cl1—C181.743 (2)C9—H90.93
S1—C21.752 (2)C10—C111.376 (4)
S1—C11.768 (2)C10—H100.93
O1—C11.207 (3)C11—C121.388 (4)
O2—C31.211 (3)C11—H110.93
O3—C91.332 (3)C12—C131.368 (4)
O3—C81.380 (3)C12—H120.93
O4—C61.216 (3)C13—H130.93
N1—C11.381 (3)C14—C151.511 (3)
N1—C31.383 (3)C14—H14A0.97
N1—C141.472 (3)C14—H14B0.97
C2—C41.341 (3)C15—C201.381 (3)
C2—C31.494 (3)C15—C161.383 (3)
C4—C51.450 (3)C16—C171.381 (3)
C4—H40.93C16—H160.93
C5—C91.353 (3)C17—C181.378 (3)
C5—C61.465 (3)C17—H170.93
C6—C71.472 (3)C18—C191.368 (4)
C7—C81.382 (3)C19—C201.393 (4)
C7—C101.396 (4)C19—H190.93
C8—C131.393 (4)C20—H200.93
C2—S1—C191.72 (11)C7—C10—H10119.8
C9—O3—C8118.1 (2)C10—C11—C12120.1 (3)
C1—N1—C3116.26 (19)C10—C11—H11120
C1—N1—C14122.18 (19)C12—C11—H11120
C3—N1—C14121.56 (19)C13—C12—C11121.1 (3)
O1—C1—N1124.8 (2)C13—C12—H12119.4
O1—C1—S1124.01 (19)C11—C12—H12119.4
N1—C1—S1111.23 (17)C12—C13—C8118.1 (3)
C4—C2—C3117.6 (2)C12—C13—H13121
C4—C2—S1132.29 (19)C8—C13—H13121
C3—C2—S1110.10 (16)N1—C14—C15112.01 (19)
O2—C3—N1123.4 (2)N1—C14—H14A109.2
O2—C3—C2126.0 (2)C15—C14—H14A109.2
N1—C3—C2110.65 (19)N1—C14—H14B109.2
C2—C4—C5134.0 (2)C15—C14—H14B109.2
C2—C4—H4113H14A—C14—H14B107.9
C5—C4—H4113C20—C15—C16118.7 (2)
C9—C5—C4116.9 (2)C20—C15—C14120.9 (2)
C9—C5—C6118.3 (2)C16—C15—C14120.4 (2)
C4—C5—C6124.8 (2)C17—C16—C15121.2 (2)
O4—C6—C5123.1 (2)C17—C16—H16119.4
O4—C6—C7122.0 (2)C15—C16—H16119.4
C5—C6—C7114.9 (2)C18—C17—C16118.9 (2)
C8—C7—C10118.1 (2)C18—C17—H17120.5
C8—C7—C6120.6 (2)C16—C17—H17120.5
C10—C7—C6121.3 (2)C19—C18—C17121.3 (2)
O3—C8—C7121.4 (2)C19—C18—Cl1119.3 (2)
O3—C8—C13116.3 (2)C17—C18—Cl1119.4 (2)
C7—C8—C13122.3 (3)C18—C19—C20119.0 (2)
O3—C9—C5126.7 (2)C18—C19—H19120.5
O3—C9—H9116.7C20—C19—H19120.5
C5—C9—H9116.7C15—C20—C19120.8 (2)
C11—C10—C7120.3 (3)C15—C20—H20119.6
C11—C10—H10119.8C19—C20—H20119.6
C3—N1—C1—O1179.6 (2)C9—O3—C8—C13179.8 (2)
C14—N1—C1—O10.2 (4)C10—C7—C8—O3179.6 (2)
C3—N1—C1—S10.7 (3)C6—C7—C8—O30.0 (4)
C14—N1—C1—S1179.58 (16)C10—C7—C8—C130.1 (4)
C2—S1—C1—O1178.8 (2)C6—C7—C8—C13179.7 (2)
C2—S1—C1—N11.40 (18)C8—O3—C9—C50.2 (4)
C1—S1—C2—C4176.3 (2)C4—C5—C9—O3179.9 (2)
C1—S1—C2—C31.72 (17)C6—C5—C9—O30.1 (4)
C1—N1—C3—O2179.7 (2)C8—C7—C10—C110.2 (4)
C14—N1—C3—O20.6 (4)C6—C7—C10—C11179.4 (2)
C1—N1—C3—C20.7 (3)C7—C10—C11—C120.3 (4)
C14—N1—C3—C2179.11 (19)C10—C11—C12—C130.1 (4)
C4—C2—C3—O23.0 (4)C11—C12—C13—C80.2 (4)
S1—C2—C3—O2178.6 (2)O3—C8—C13—C12179.4 (2)
C4—C2—C3—N1176.7 (2)C7—C8—C13—C120.3 (4)
S1—C2—C3—N11.7 (2)C1—N1—C14—C15100.8 (3)
C3—C2—C4—C5179.0 (2)C3—N1—C14—C1579.5 (3)
S1—C2—C4—C51.1 (4)N1—C14—C15—C20115.3 (2)
C2—C4—C5—C9175.3 (3)N1—C14—C15—C1665.7 (3)
C2—C4—C5—C64.9 (4)C20—C15—C16—C170.6 (4)
C9—C5—C6—O4179.5 (3)C14—C15—C16—C17179.7 (2)
C4—C5—C6—O40.2 (4)C15—C16—C17—C180.5 (4)
C9—C5—C6—C70.0 (3)C16—C17—C18—C190.3 (4)
C4—C5—C6—C7179.7 (2)C16—C17—C18—Cl1179.2 (2)
O4—C6—C7—C8179.5 (3)C17—C18—C19—C200.9 (4)
C5—C6—C7—C80.1 (3)Cl1—C18—C19—C20179.9 (2)
O4—C6—C7—C100.8 (4)C16—C15—C20—C190.0 (4)
C5—C6—C7—C10179.7 (2)C14—C15—C20—C19179.0 (2)
C9—O3—C8—C70.2 (4)C18—C19—C20—C150.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O20.932.422.836 (3)107
C13—H13···O1i0.932.573.443 (4)157
C14—H14A···O10.972.522.864 (3)101
C14—H14B···O2ii0.972.423.361 (3)164
C16—H16···O10.932.893.585 (4)133
C19—H19···O4iii0.932.713.351 (3)127
C20—H20···O4iii0.932.833.420 (3)122
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+2, z+1; (iii) x, y, z+1.
 

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