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The title compound, C23H20N4O4S, was synthesized by the intermolecular [3 + 2] cyclo­addition of azomethine yl­ide, derived from isatin and sarcosine by a de­carboxyl­ative route, and 2-benzo­[1,3]­dioxol-5-yl­methyl­ene-5,6-di­hydro-imidazo­[2,1-b]­thia­zol-3-one. In the mol­ecule, two spiro junctions link a planar 2-ox­indole ring, a pyrrolidine ring in an envelope conformation and a 5,6-di­hydro-imidazo­[2,1-b]thia­zol-3-one ring. Two mol­ecules are connected into a dimer by two N—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019512/om6173sup1.cif
Contains datablocks DS, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019512/om6173Isup2.hkl
Contains datablock I

CCDC reference: 225710

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.107
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.73 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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.

1-Methyl-spiro[2.3']oxindole-spiro[3.2"]5",6"-dihydro-imidazo [2",1"-b]thiazol-3"-one -4-(2-benzo[1,3]dioxol-5-yl)-pyrrolidine top
Crystal data top
C23H20N4O4SZ = 2
Mr = 448.49F(000) = 468
Triclinic, P1Dx = 1.397 Mg m3
Hall symbol: -P 1Melting point = 543–544 K
a = 8.741 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.255 (4) ÅCell parameters from 1010 reflections
c = 14.097 (7) Åθ = 2.5–26.5°
α = 85.690 (7)°µ = 0.19 mm1
β = 72.206 (7)°T = 293 K
γ = 79.169 (8)°Block, colorless
V = 1066.4 (9) Å30.28 × 0.22 × 0.20 mm
Data collection top
CCD area detector
diffractometer
4388 independent reflections
Radiation source: fine-focus sealed tube3798 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 26.5°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS Bruker, 1997)
h = 1010
Tmin = 0.863, Tmax = 0.960k = 1111
14787 measured reflectionsl = 1717
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034 w = 1/[σ2(Fo2) + (0.084P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.107(Δ/σ)max < 0.001
S = 1.09Δρmax = 0.29 e Å3
4388 reflectionsΔρmin = 0.21 e Å3
290 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
xyzUiso*/Ueq
S10.32348 (5)0.52740 (4)0.21667 (3)0.03640 (12)
N10.43770 (16)0.25981 (13)0.25712 (9)0.0367 (3)
N20.3203 (2)0.27016 (15)0.13435 (11)0.0513 (4)
N30.69036 (15)0.59321 (14)0.30717 (9)0.0357 (3)
N40.69629 (18)0.59354 (15)0.05818 (9)0.0442 (3)
H40.69660.63590.00170.053*
O10.54625 (14)0.27798 (12)0.38221 (8)0.0394 (3)
O20.53801 (16)0.78017 (12)0.16051 (9)0.0490 (3)
O30.05404 (17)0.97182 (14)0.35571 (11)0.0602 (4)
O40.22692 (16)0.90232 (16)0.50477 (12)0.0680 (4)
C10.46612 (17)0.49963 (14)0.29192 (10)0.0283 (3)
C20.48738 (17)0.33329 (15)0.31813 (10)0.0302 (3)
C30.35882 (18)0.34049 (16)0.19407 (10)0.0339 (3)
C40.3765 (4)0.1123 (2)0.15350 (18)0.0774 (7)
H4A0.45510.06800.09380.093*
H4B0.28490.06020.17310.093*
C50.4559 (3)0.10349 (17)0.23800 (14)0.0527 (5)
H5A0.39820.05120.29620.063*
H5B0.56980.05710.21640.063*
C60.41472 (17)0.59236 (15)0.38852 (10)0.0312 (3)
H60.42680.52250.44260.037*
C70.54808 (19)0.68544 (17)0.37120 (11)0.0370 (3)
H7A0.52100.77840.33840.044*
H7B0.56580.70450.43340.044*
C80.63814 (17)0.53925 (15)0.23012 (10)0.0307 (3)
C90.61488 (19)0.65574 (16)0.14701 (11)0.0356 (3)
C100.7801 (2)0.45195 (18)0.06871 (11)0.0400 (3)
C110.8772 (3)0.3571 (2)0.00492 (14)0.0598 (5)
H110.88930.38080.07180.072*
C120.9564 (3)0.2254 (2)0.02362 (16)0.0675 (6)
H121.02200.15900.02490.081*
C130.9401 (2)0.1904 (2)0.12233 (16)0.0602 (5)
H130.99580.10150.13970.072*
C140.8415 (2)0.28645 (19)0.19607 (13)0.0461 (4)
H140.83200.26360.26280.055*
C150.75789 (18)0.41621 (16)0.16905 (11)0.0342 (3)
C160.24205 (18)0.67487 (15)0.42160 (11)0.0328 (3)
C170.1869 (2)0.79171 (16)0.36411 (11)0.0377 (3)
H170.25550.82160.30430.045*
C180.0281 (2)0.85975 (16)0.39987 (12)0.0402 (4)
C190.0743 (2)0.81805 (18)0.48832 (14)0.0446 (4)
C200.0238 (2)0.7064 (2)0.54605 (14)0.0510 (4)
H200.09350.67910.60630.061*
C210.1377 (2)0.63450 (18)0.51080 (12)0.0415 (4)
H210.17610.55740.54840.050*
C220.2136 (3)1.0048 (2)0.42374 (17)0.0625 (5)
H22A0.23291.10400.44780.075*
H22B0.29440.99850.39060.075*
C230.8363 (2)0.6593 (2)0.27220 (14)0.0552 (5)
H23A0.92440.58990.23270.083*
H23B0.86470.68610.32830.083*
H23C0.81630.74550.23250.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0434 (2)0.02935 (19)0.0429 (2)0.00033 (14)0.02566 (17)0.00157 (14)
N10.0499 (8)0.0256 (6)0.0383 (7)0.0048 (5)0.0199 (6)0.0010 (5)
N20.0831 (11)0.0375 (7)0.0468 (8)0.0158 (7)0.0363 (8)0.0016 (6)
N30.0366 (7)0.0453 (7)0.0287 (6)0.0104 (5)0.0118 (5)0.0049 (5)
N40.0609 (9)0.0450 (7)0.0254 (6)0.0082 (6)0.0127 (6)0.0036 (5)
O10.0478 (6)0.0364 (5)0.0348 (5)0.0003 (4)0.0190 (5)0.0047 (4)
O20.0722 (8)0.0302 (6)0.0443 (6)0.0048 (5)0.0204 (6)0.0032 (5)
O30.0650 (8)0.0454 (7)0.0684 (9)0.0130 (6)0.0313 (7)0.0016 (6)
O40.0430 (7)0.0629 (9)0.0875 (10)0.0112 (6)0.0152 (7)0.0050 (8)
C10.0326 (7)0.0273 (6)0.0266 (6)0.0016 (5)0.0133 (5)0.0002 (5)
C20.0313 (7)0.0295 (7)0.0275 (7)0.0017 (5)0.0078 (5)0.0001 (5)
C30.0412 (8)0.0326 (7)0.0303 (7)0.0084 (6)0.0137 (6)0.0022 (5)
C40.139 (2)0.0374 (10)0.0813 (15)0.0134 (12)0.0709 (16)0.0025 (10)
C50.0837 (13)0.0279 (8)0.0545 (10)0.0077 (8)0.0333 (10)0.0010 (7)
C60.0372 (7)0.0305 (7)0.0263 (6)0.0017 (6)0.0119 (6)0.0020 (5)
C70.0448 (8)0.0383 (8)0.0302 (7)0.0079 (6)0.0131 (6)0.0065 (6)
C80.0365 (7)0.0311 (7)0.0260 (6)0.0060 (6)0.0116 (6)0.0001 (5)
C90.0458 (8)0.0346 (7)0.0302 (7)0.0120 (6)0.0146 (6)0.0025 (6)
C100.0435 (9)0.0451 (9)0.0310 (7)0.0088 (7)0.0091 (6)0.0038 (6)
C110.0672 (12)0.0692 (13)0.0349 (9)0.0031 (10)0.0053 (8)0.0141 (8)
C120.0617 (12)0.0663 (13)0.0597 (12)0.0089 (10)0.0023 (10)0.0261 (10)
C130.0488 (10)0.0537 (11)0.0663 (12)0.0097 (8)0.0093 (9)0.0076 (9)
C140.0384 (8)0.0494 (9)0.0455 (9)0.0020 (7)0.0113 (7)0.0003 (7)
C150.0331 (7)0.0386 (8)0.0303 (7)0.0058 (6)0.0081 (6)0.0033 (6)
C160.0394 (8)0.0274 (6)0.0322 (7)0.0025 (6)0.0126 (6)0.0045 (5)
C170.0473 (9)0.0314 (7)0.0341 (7)0.0028 (6)0.0137 (6)0.0025 (6)
C180.0506 (9)0.0288 (7)0.0453 (9)0.0005 (6)0.0236 (7)0.0051 (6)
C190.0381 (8)0.0391 (8)0.0564 (10)0.0014 (6)0.0163 (7)0.0108 (7)
C200.0436 (9)0.0508 (10)0.0479 (10)0.0042 (7)0.0014 (8)0.0030 (8)
C210.0441 (9)0.0375 (8)0.0383 (8)0.0021 (6)0.0095 (7)0.0032 (6)
C220.0593 (12)0.0473 (10)0.0856 (15)0.0147 (9)0.0394 (11)0.0167 (10)
C230.0503 (10)0.0756 (13)0.0464 (10)0.0293 (9)0.0109 (8)0.0098 (9)
Geometric parameters (Å, º) top
S1—C31.7353 (17)C6—H60.9800
S1—C11.8421 (15)C7—H7A0.9700
N1—C21.3483 (19)C7—H7B0.9700
N1—C31.3800 (19)C8—C151.511 (2)
N1—C51.462 (2)C8—C91.565 (2)
N2—C31.258 (2)C10—C111.374 (2)
N2—C41.483 (2)C10—C151.391 (2)
N3—C81.4518 (18)C11—C121.381 (3)
N3—C231.452 (2)C11—H110.9300
N3—C71.456 (2)C12—C131.375 (3)
N4—C91.347 (2)C12—H120.9300
N4—C101.397 (2)C13—C141.385 (3)
N4—H40.8600C13—H130.9300
O1—C21.2077 (17)C14—C151.376 (2)
O2—C91.2157 (19)C14—H140.9300
O3—C181.3695 (19)C16—C211.382 (2)
O3—C221.423 (3)C16—C171.403 (2)
O4—C191.374 (2)C17—C181.367 (2)
O4—C221.420 (3)C17—H170.9300
C1—C21.5460 (19)C18—C191.371 (3)
C1—C61.5651 (19)C19—C201.359 (2)
C1—C81.585 (2)C20—C211.396 (2)
C4—C51.542 (3)C20—H200.9300
C4—H4A0.9700C21—H210.9300
C4—H4B0.9700C22—H22A0.9700
C5—H5A0.9700C22—H22B0.9700
C5—H5B0.9700C23—H23A0.9600
C6—C161.506 (2)C23—H23B0.9600
C6—C71.527 (2)C23—H23C0.9600
C3—S1—C191.46 (6)C15—C8—C1115.56 (12)
C2—N1—C3118.21 (12)C9—C8—C1109.15 (11)
C2—N1—C5133.04 (13)O2—C9—N4126.35 (14)
C3—N1—C5108.67 (12)O2—C9—C8125.98 (13)
C3—N2—C4106.04 (14)N4—C9—C8107.67 (13)
C8—N3—C23115.59 (12)C11—C10—C15121.64 (16)
C8—N3—C7106.84 (12)C11—C10—N4128.20 (16)
C23—N3—C7115.15 (14)C15—C10—N4110.12 (13)
C9—N4—C10111.97 (12)C10—C11—C12117.82 (18)
C9—N4—H4124.0C10—C11—H11121.1
C10—N4—H4124.0C12—C11—H11121.1
C18—O3—C22105.59 (15)C13—C12—C11121.31 (18)
C19—O4—C22105.53 (15)C13—C12—H12119.3
C2—C1—C6110.54 (11)C11—C12—H12119.3
C2—C1—C8109.00 (11)C12—C13—C14120.48 (18)
C6—C1—C8104.21 (11)C12—C13—H13119.8
C2—C1—S1104.66 (9)C14—C13—H13119.8
C6—C1—S1116.84 (9)C15—C14—C13118.94 (17)
C8—C1—S1111.52 (9)C15—C14—H14120.5
O1—C2—N1125.45 (13)C13—C14—H14120.5
O1—C2—C1123.90 (13)C14—C15—C10119.73 (14)
N1—C2—C1110.59 (11)C14—C15—C8131.85 (14)
N2—C3—N1117.30 (14)C10—C15—C8108.42 (13)
N2—C3—S1131.27 (12)C21—C16—C17120.01 (14)
N1—C3—S1111.38 (11)C21—C16—C6118.77 (13)
N2—C4—C5107.50 (14)C17—C16—C6121.22 (13)
N2—C4—H4A110.2C18—C17—C16117.11 (15)
C5—C4—H4A110.2C18—C17—H17121.4
N2—C4—H4B110.2C16—C17—H17121.4
C5—C4—H4B110.2C17—C18—O3127.66 (16)
H4A—C4—H4B108.5C17—C18—C19122.26 (15)
N1—C5—C4100.48 (13)O3—C18—C19110.06 (15)
N1—C5—H5A111.7C20—C19—C18121.90 (15)
C4—C5—H5A111.7C20—C19—O4128.15 (17)
N1—C5—H5B111.7C18—C19—O4109.94 (15)
C4—C5—H5B111.7C19—C20—C21116.93 (16)
H5A—C5—H5B109.4C19—C20—H20121.5
C16—C6—C7115.70 (12)C21—C20—H20121.5
C16—C6—C1117.18 (11)C16—C21—C20121.79 (15)
C7—C6—C1104.28 (11)C16—C21—H21119.1
C16—C6—H6106.3C20—C21—H21119.1
C7—C6—H6106.3O4—C22—O3108.68 (14)
C1—C6—H6106.3O4—C22—H22A110.0
N3—C7—C6102.78 (12)O3—C22—H22A110.0
N3—C7—H7A111.2O4—C22—H22B110.0
C6—C7—H7A111.2O3—C22—H22B110.0
N3—C7—H7B111.2H22A—C22—H22B108.3
C6—C7—H7B111.2N3—C23—H23A109.5
H7A—C7—H7B109.1N3—C23—H23B109.5
N3—C8—C15114.90 (12)H23A—C23—H23B109.5
N3—C8—C9114.45 (12)N3—C23—H23C109.5
C15—C8—C9101.40 (11)H23A—C23—H23C109.5
N3—C8—C1101.79 (11)H23B—C23—H23C109.5
C3—S1—C1—C217.39 (10)C10—N4—C9—O2176.40 (16)
C3—S1—C1—C6139.99 (11)C10—N4—C9—C83.15 (18)
C3—S1—C1—C8100.32 (10)N3—C8—C9—O249.5 (2)
C3—N1—C2—O1173.98 (14)C15—C8—C9—O2173.78 (15)
C5—N1—C2—O19.5 (3)C1—C8—C9—O263.82 (19)
C3—N1—C2—C18.61 (18)N3—C8—C9—N4130.07 (14)
C5—N1—C2—C1167.92 (17)C15—C8—C9—N45.77 (15)
C6—C1—C2—O138.38 (19)C1—C8—C9—N4116.63 (13)
C8—C1—C2—O175.58 (17)C9—N4—C10—C11178.91 (18)
S1—C1—C2—O1165.00 (12)C9—N4—C10—C151.17 (19)
C6—C1—C2—N1144.16 (12)C15—C10—C11—C121.6 (3)
C8—C1—C2—N1101.87 (13)N4—C10—C11—C12175.92 (19)
S1—C1—C2—N117.55 (13)C10—C11—C12—C130.6 (3)
C4—N2—C3—N10.2 (2)C11—C12—C13—C140.8 (4)
C4—N2—C3—S1176.92 (17)C12—C13—C14—C151.1 (3)
C2—N1—C3—N2176.68 (15)C13—C14—C15—C103.3 (3)
C5—N1—C3—N20.7 (2)C13—C14—C15—C8177.42 (17)
C2—N1—C3—S15.67 (18)C11—C10—C15—C143.6 (3)
C5—N1—C3—S1177.00 (12)N4—C10—C15—C14174.35 (14)
C1—S1—C3—N2168.72 (17)C11—C10—C15—C8176.97 (16)
C1—S1—C3—N114.05 (12)N4—C10—C15—C85.12 (18)
C3—N2—C4—C50.3 (3)N3—C8—C15—C1449.0 (2)
C2—N1—C5—C4176.03 (19)C9—C8—C15—C14172.94 (16)
C3—N1—C5—C40.7 (2)C1—C8—C15—C1469.2 (2)
N2—C4—C5—N10.7 (2)N3—C8—C15—C10130.43 (14)
C2—C1—C6—C16108.77 (13)C9—C8—C15—C106.44 (15)
C8—C1—C6—C16134.26 (12)C1—C8—C15—C10111.42 (14)
S1—C1—C6—C1610.74 (16)C7—C6—C16—C21121.73 (15)
C2—C1—C6—C7121.91 (12)C1—C6—C16—C21114.58 (15)
C8—C1—C6—C74.94 (13)C7—C6—C16—C1757.66 (18)
S1—C1—C6—C7118.58 (11)C1—C6—C16—C1766.03 (18)
C8—N3—C7—C646.05 (14)C21—C16—C17—C180.9 (2)
C23—N3—C7—C6175.89 (13)C6—C16—C17—C18179.75 (13)
C16—C6—C7—N3159.62 (12)C16—C17—C18—O3177.54 (15)
C1—C6—C7—N329.42 (13)C16—C17—C18—C190.6 (2)
C23—N3—C8—C1562.85 (18)C22—O3—C18—C17178.79 (17)
C7—N3—C8—C15167.57 (12)C22—O3—C18—C192.92 (19)
C23—N3—C8—C953.92 (18)C17—C18—C19—C200.2 (3)
C7—N3—C8—C975.67 (15)O3—C18—C19—C20178.56 (17)
C23—N3—C8—C1171.50 (14)C17—C18—C19—O4178.60 (15)
C7—N3—C8—C141.91 (14)O3—C18—C19—O40.2 (2)
C2—C1—C8—N396.81 (12)C22—O4—C19—C20178.72 (19)
C6—C1—C8—N321.21 (13)C22—O4—C19—C182.6 (2)
S1—C1—C8—N3148.12 (9)C18—C19—C20—C210.6 (3)
C2—C1—C8—C1528.40 (15)O4—C19—C20—C21177.95 (17)
C6—C1—C8—C15146.43 (11)C17—C16—C21—C200.5 (2)
S1—C1—C8—C1586.66 (12)C6—C16—C21—C20179.89 (15)
C2—C1—C8—C9141.85 (11)C19—C20—C21—C160.2 (3)
C6—C1—C8—C9100.12 (12)C19—O4—C22—O34.4 (2)
S1—C1—C8—C926.79 (13)C18—O3—C22—O44.5 (2)
 

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