Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017471/ww6108sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017471/ww6108Isup2.hkl |
CCDC reference: 222865
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.057
- wR factor = 0.104
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .. ? PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Expl... P 2yc PLAT230_ALERT_2_C Hirshfeld Test Diff for C13 - C14 = 5.05 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang.. 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion
A mixture of 2-(2-chlorobenzylidene)benzo[4,5]imidazo[2,1-b]thiazol-3-one (1 mmol), isatin (1 mmol) and sarcosine (1 mmol) were reflux in methanol (60 ml) until total consumption of the starting material, as evidenced by thin-layer chromatography. After evaporation of the solvent, the residue was separated by column chromatography (silica gel, petroleum ether/ethyl acetate = 5:1) to give the title compound (I). M.p.:516–518 K; IR (KBr): 1751.5, 1685.9 (C\dn O), 1612.6 (C═N) cm−1; 1H NMR (CDCl3, δ, p.p.m.): 2.32 (3H, s), 3.67 (1H, m), 4.24 (1H, m), 4.69 (1H, m), 6.69–7.87 (12H, m), 7.89 (1H, br); 20 mg of (I) was dissolved in 15 ml dioxane, the solution was kept at room temperature for 10 d by natural evaporation to give colorless single crystals of (I), suitable for X-ray analysis.
H atoms were placed at geometrically calculated positions (C—H = 0.93–0.98 Å) and refined in the riding model approximation with Uiso(H) = 1.2Ueq(carrier atom).
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.
Fig. 1. The molecular structure of (I), showing the atom-numbering scheme, drawn with 30% probability ellipsoids. | |
Fig. 2. The crystal packing diagram of (I), viewed along the c axis. |
C26H19ClN4O2S·0.5C4H8O2 | F(000) = 1104 |
Mr = 531.01 | Dx = 1.414 Mg m−3 |
Monoclinic, P21/c | Melting point = 516–518 K |
Hall symbol: P 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.085 (3) Å | Cell parameters from 911 reflections |
b = 29.272 (9) Å | θ = 2.5–24.6° |
c = 8.561 (3) Å | µ = 0.28 mm−1 |
β = 99.287 (6)° | T = 293 K |
V = 2494.2 (13) Å3 | Block, colorless |
Z = 4 | 0.18 × 0.16 × 0.14 mm |
Bruker SMART CCD area-detector diffractometer | 5109 independent reflections |
Radiation source: fine-focus sealed tube | 2883 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −11→12 |
Tmin = 0.924, Tmax = 0.960 | k = −36→34 |
14310 measured reflections | l = −8→10 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.057 | w = 1/[σ2(Fo2) + (0.084P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.104 | (Δ/σ)max = 0.001 |
S = 1.02 | Δρmax = 0.21 e Å−3 |
5109 reflections | Δρmin = −0.25 e Å−3 |
335 parameters |
C26H19ClN4O2S·0.5C4H8O2 | V = 2494.2 (13) Å3 |
Mr = 531.01 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.085 (3) Å | µ = 0.28 mm−1 |
b = 29.272 (9) Å | T = 293 K |
c = 8.561 (3) Å | 0.18 × 0.16 × 0.14 mm |
β = 99.287 (6)° |
Bruker SMART CCD area-detector diffractometer | 5109 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 2883 reflections with I > 2σ(I) |
Tmin = 0.924, Tmax = 0.960 | Rint = 0.069 |
14310 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.21 e Å−3 |
5109 reflections | Δρmin = −0.25 e Å−3 |
335 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 1.01570 (8) | 0.39685 (2) | 0.34987 (9) | 0.0404 (2) | |
Cl1 | 1.30898 (10) | 0.32301 (4) | 0.20570 (14) | 0.0859 (4) | |
N1 | 1.1313 (2) | 0.46458 (8) | 0.1893 (3) | 0.0376 (6) | |
N2 | 1.0369 (2) | 0.40382 (7) | 0.0521 (3) | 0.0330 (6) | |
N3 | 0.8000 (2) | 0.28879 (7) | 0.1905 (3) | 0.0378 (6) | |
N4 | 0.6542 (2) | 0.38362 (8) | 0.3273 (3) | 0.0417 (6) | |
H4A | 0.6121 | 0.3967 | 0.3947 | 0.050* | |
O1 | 0.9865 (2) | 0.33312 (6) | −0.0522 (3) | 0.0517 (6) | |
O2 | 0.8068 (2) | 0.34352 (7) | 0.5018 (2) | 0.0513 (6) | |
C1 | 1.0680 (3) | 0.42630 (9) | 0.1956 (3) | 0.0324 (7) | |
C2 | 1.1430 (3) | 0.46887 (9) | 0.0279 (4) | 0.0351 (7) | |
C3 | 1.1987 (3) | 0.50387 (9) | −0.0488 (4) | 0.0420 (8) | |
H3 | 1.2386 | 0.5289 | 0.0070 | 0.050* | |
C4 | 1.1934 (3) | 0.50051 (10) | −0.2097 (4) | 0.0474 (8) | |
H4 | 1.2307 | 0.5237 | −0.2630 | 0.057* | |
C5 | 1.1342 (3) | 0.46354 (10) | −0.2948 (4) | 0.0485 (8) | |
H5 | 1.1313 | 0.4628 | −0.4039 | 0.058* | |
C6 | 1.0791 (3) | 0.42766 (10) | −0.2212 (4) | 0.0436 (8) | |
H6 | 1.0403 | 0.4025 | −0.2773 | 0.052* | |
C7 | 1.0853 (3) | 0.43153 (9) | −0.0604 (3) | 0.0335 (7) | |
C8 | 0.9940 (3) | 0.35917 (10) | 0.0562 (4) | 0.0361 (7) | |
C9 | 0.9609 (3) | 0.34780 (9) | 0.2211 (3) | 0.0323 (7) | |
C10 | 0.8051 (3) | 0.33848 (9) | 0.2113 (3) | 0.0328 (7) | |
C11 | 0.7090 (3) | 0.36394 (9) | 0.0873 (3) | 0.0338 (7) | |
C12 | 0.6905 (3) | 0.36362 (10) | −0.0752 (4) | 0.0485 (8) | |
H12 | 0.7456 | 0.3460 | −0.1287 | 0.058* | |
C13 | 0.5880 (4) | 0.39006 (12) | −0.1585 (4) | 0.0605 (10) | |
H13 | 0.5759 | 0.3907 | −0.2685 | 0.073* | |
C14 | 0.5045 (4) | 0.41522 (12) | −0.0798 (5) | 0.0628 (10) | |
H14 | 0.4362 | 0.4325 | −0.1376 | 0.075* | |
C15 | 0.5199 (3) | 0.41535 (11) | 0.0826 (4) | 0.0545 (9) | |
H15 | 0.4628 | 0.4322 | 0.1357 | 0.065* | |
C16 | 0.6226 (3) | 0.38978 (9) | 0.1635 (4) | 0.0382 (7) | |
C17 | 0.7593 (3) | 0.35461 (9) | 0.3676 (4) | 0.0359 (7) | |
C18 | 0.9113 (3) | 0.27005 (9) | 0.3026 (4) | 0.0435 (8) | |
H18A | 0.9287 | 0.2385 | 0.2778 | 0.052* | |
H18B | 0.8931 | 0.2718 | 0.4102 | 0.052* | |
C19 | 1.0293 (3) | 0.30089 (9) | 0.2795 (4) | 0.0388 (7) | |
H19 | 1.0677 | 0.2882 | 0.1907 | 0.047* | |
C20 | 1.1425 (3) | 0.30421 (9) | 0.4177 (4) | 0.0447 (8) | |
C21 | 1.2738 (3) | 0.31241 (11) | 0.3947 (5) | 0.0571 (10) | |
C22 | 1.3798 (4) | 0.31379 (13) | 0.5190 (6) | 0.0770 (13) | |
H22 | 1.4670 | 0.3183 | 0.4996 | 0.092* | |
C23 | 1.3557 (4) | 0.30847 (13) | 0.6715 (6) | 0.0797 (13) | |
H23 | 1.4267 | 0.3090 | 0.7556 | 0.096* | |
C24 | 1.2267 (4) | 0.30243 (11) | 0.6994 (5) | 0.0672 (11) | |
H24 | 1.2099 | 0.2997 | 0.8026 | 0.081* | |
C25 | 1.1218 (3) | 0.30045 (11) | 0.5738 (4) | 0.0555 (9) | |
H25 | 1.0347 | 0.2965 | 0.5944 | 0.067* | |
C26 | 0.6711 (3) | 0.26742 (10) | 0.2007 (4) | 0.0563 (9) | |
H26A | 0.6520 | 0.2704 | 0.3065 | 0.084* | |
H26B | 0.6747 | 0.2356 | 0.1741 | 0.084* | |
H26C | 0.6016 | 0.2821 | 0.1281 | 0.084* | |
O3 | 0.5433 (2) | 0.45487 (7) | 0.4872 (3) | 0.0491 (6) | |
C27 | 0.6258 (3) | 0.48761 (11) | 0.5810 (4) | 0.0492 (9) | |
H27A | 0.7197 | 0.4806 | 0.5802 | 0.059* | |
H27B | 0.6097 | 0.4861 | 0.6896 | 0.059* | |
C28 | 0.4045 (3) | 0.46540 (10) | 0.4825 (4) | 0.0488 (8) | |
H28A | 0.3822 | 0.4633 | 0.5882 | 0.059* | |
H28B | 0.3500 | 0.4434 | 0.4159 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0556 (5) | 0.0336 (4) | 0.0317 (4) | −0.0061 (4) | 0.0059 (4) | −0.0020 (4) |
Cl1 | 0.0537 (6) | 0.1073 (8) | 0.1049 (9) | −0.0045 (6) | 0.0371 (6) | 0.0248 (7) |
N1 | 0.0379 (14) | 0.0294 (13) | 0.0432 (16) | −0.0076 (11) | −0.0001 (12) | −0.0011 (12) |
N2 | 0.0401 (14) | 0.0265 (13) | 0.0321 (14) | −0.0070 (11) | 0.0053 (11) | −0.0023 (11) |
N3 | 0.0351 (14) | 0.0267 (13) | 0.0527 (17) | −0.0030 (11) | 0.0103 (13) | 0.0001 (12) |
N4 | 0.0422 (15) | 0.0438 (15) | 0.0412 (16) | 0.0086 (12) | 0.0132 (12) | 0.0007 (13) |
O1 | 0.0804 (16) | 0.0337 (12) | 0.0476 (14) | −0.0175 (11) | 0.0310 (12) | −0.0132 (11) |
O2 | 0.0594 (14) | 0.0593 (14) | 0.0353 (13) | 0.0141 (12) | 0.0081 (11) | 0.0074 (11) |
C1 | 0.0307 (16) | 0.0283 (16) | 0.0359 (17) | 0.0024 (13) | −0.0015 (13) | −0.0010 (14) |
C2 | 0.0304 (16) | 0.0319 (17) | 0.0424 (19) | −0.0023 (13) | 0.0038 (14) | 0.0020 (15) |
C3 | 0.0372 (18) | 0.0291 (17) | 0.060 (2) | −0.0073 (14) | 0.0075 (16) | −0.0025 (16) |
C4 | 0.049 (2) | 0.0372 (19) | 0.059 (2) | −0.0070 (16) | 0.0192 (17) | 0.0089 (17) |
C5 | 0.060 (2) | 0.0444 (19) | 0.044 (2) | −0.0063 (17) | 0.0193 (17) | 0.0039 (17) |
C6 | 0.056 (2) | 0.0368 (17) | 0.0403 (19) | −0.0106 (16) | 0.0161 (16) | −0.0033 (15) |
C7 | 0.0359 (16) | 0.0248 (15) | 0.0406 (18) | −0.0023 (13) | 0.0084 (14) | 0.0011 (14) |
C8 | 0.0366 (17) | 0.0310 (17) | 0.0421 (19) | −0.0051 (14) | 0.0111 (15) | −0.0040 (15) |
C9 | 0.0400 (17) | 0.0237 (15) | 0.0346 (17) | −0.0024 (13) | 0.0099 (14) | −0.0017 (13) |
C10 | 0.0377 (16) | 0.0290 (16) | 0.0326 (17) | −0.0003 (13) | 0.0086 (13) | −0.0020 (13) |
C11 | 0.0383 (17) | 0.0260 (15) | 0.0356 (18) | −0.0041 (13) | 0.0015 (14) | 0.0016 (14) |
C12 | 0.058 (2) | 0.0418 (19) | 0.044 (2) | −0.0094 (17) | 0.0046 (17) | −0.0015 (17) |
C13 | 0.071 (3) | 0.059 (2) | 0.044 (2) | −0.016 (2) | −0.014 (2) | 0.0172 (19) |
C14 | 0.054 (2) | 0.060 (2) | 0.069 (3) | 0.0013 (19) | −0.008 (2) | 0.018 (2) |
C15 | 0.044 (2) | 0.050 (2) | 0.068 (3) | 0.0083 (17) | 0.0037 (18) | 0.0130 (19) |
C16 | 0.0357 (17) | 0.0336 (17) | 0.0438 (19) | −0.0020 (15) | 0.0022 (15) | 0.0043 (15) |
C17 | 0.0376 (18) | 0.0320 (17) | 0.0385 (19) | 0.0005 (14) | 0.0076 (15) | 0.0052 (15) |
C18 | 0.0431 (19) | 0.0304 (16) | 0.060 (2) | 0.0026 (15) | 0.0184 (17) | 0.0068 (16) |
C19 | 0.0393 (17) | 0.0282 (16) | 0.052 (2) | 0.0045 (14) | 0.0179 (16) | 0.0060 (15) |
C20 | 0.0369 (18) | 0.0296 (17) | 0.068 (2) | 0.0051 (14) | 0.0095 (17) | 0.0112 (17) |
C21 | 0.043 (2) | 0.048 (2) | 0.082 (3) | 0.0035 (17) | 0.014 (2) | 0.015 (2) |
C22 | 0.044 (2) | 0.066 (3) | 0.118 (4) | −0.002 (2) | 0.005 (3) | 0.019 (3) |
C23 | 0.057 (3) | 0.071 (3) | 0.100 (4) | −0.007 (2) | −0.018 (3) | 0.016 (3) |
C24 | 0.070 (3) | 0.058 (2) | 0.068 (3) | −0.003 (2) | −0.006 (2) | 0.014 (2) |
C25 | 0.047 (2) | 0.054 (2) | 0.065 (3) | 0.0052 (17) | 0.0097 (19) | 0.017 (2) |
C26 | 0.048 (2) | 0.046 (2) | 0.074 (3) | −0.0126 (17) | 0.0107 (18) | 0.0006 (19) |
O3 | 0.0402 (13) | 0.0480 (13) | 0.0569 (15) | 0.0064 (11) | 0.0018 (11) | −0.0116 (11) |
C27 | 0.0374 (19) | 0.055 (2) | 0.053 (2) | 0.0019 (16) | 0.0014 (16) | −0.0045 (18) |
C28 | 0.0406 (19) | 0.049 (2) | 0.055 (2) | −0.0014 (16) | 0.0042 (16) | −0.0027 (18) |
S1—C1 | 1.730 (3) | C12—H12 | 0.9300 |
S1—C9 | 1.840 (3) | C13—C14 | 1.375 (5) |
Cl1—C21 | 1.740 (4) | C13—H13 | 0.9300 |
N1—C1 | 1.295 (3) | C14—C15 | 1.374 (5) |
N1—C2 | 1.411 (4) | C14—H14 | 0.9300 |
N2—C8 | 1.379 (3) | C15—C16 | 1.372 (4) |
N2—C1 | 1.384 (3) | C15—H15 | 0.9300 |
N2—C7 | 1.406 (3) | C18—C19 | 1.532 (4) |
N3—C26 | 1.458 (3) | C18—H18A | 0.9700 |
N3—C18 | 1.461 (3) | C18—H18B | 0.9700 |
N3—C10 | 1.465 (3) | C19—C20 | 1.509 (4) |
N4—C17 | 1.358 (3) | C19—H19 | 0.9800 |
N4—C16 | 1.399 (3) | C20—C25 | 1.390 (4) |
N4—H4A | 0.8600 | C20—C21 | 1.390 (4) |
O1—C8 | 1.194 (3) | C21—C22 | 1.382 (5) |
O2—C17 | 1.216 (3) | C22—C23 | 1.375 (5) |
C2—C3 | 1.384 (4) | C22—H22 | 0.9300 |
C2—C7 | 1.401 (4) | C23—C24 | 1.371 (5) |
C3—C4 | 1.374 (4) | C23—H23 | 0.9300 |
C3—H3 | 0.9300 | C24—C25 | 1.383 (4) |
C4—C5 | 1.385 (4) | C24—H24 | 0.9300 |
C4—H4 | 0.9300 | C25—H25 | 0.9300 |
C5—C6 | 1.387 (4) | C26—H26A | 0.9600 |
C5—H5 | 0.9300 | C26—H26B | 0.9600 |
C6—C7 | 1.372 (4) | C26—H26C | 0.9600 |
C6—H6 | 0.9300 | O3—C28 | 1.427 (3) |
C8—C9 | 1.539 (4) | O3—C27 | 1.428 (3) |
C9—C19 | 1.582 (4) | C27—C28i | 1.492 (4) |
C9—C10 | 1.583 (4) | C27—H27A | 0.9700 |
C10—C11 | 1.513 (4) | C27—H27B | 0.9700 |
C10—C17 | 1.558 (4) | C28—C27i | 1.492 (4) |
C11—C12 | 1.374 (4) | C28—H28A | 0.9700 |
C11—C16 | 1.393 (4) | C28—H28B | 0.9700 |
C12—C13 | 1.393 (4) | ||
C1—S1—C9 | 91.76 (13) | C16—C15—C14 | 117.6 (3) |
C1—N1—C2 | 103.7 (2) | C16—C15—H15 | 121.2 |
C8—N2—C1 | 117.1 (2) | C14—C15—H15 | 121.2 |
C8—N2—C7 | 135.2 (2) | C15—C16—C11 | 122.6 (3) |
C1—N2—C7 | 106.3 (2) | C15—C16—N4 | 127.4 (3) |
C26—N3—C18 | 113.4 (2) | C11—C16—N4 | 109.9 (3) |
C26—N3—C10 | 115.6 (2) | O2—C17—N4 | 125.4 (3) |
C18—N3—C10 | 106.5 (2) | O2—C17—C10 | 127.2 (3) |
C17—N4—C16 | 112.2 (2) | N4—C17—C10 | 107.4 (2) |
C17—N4—H4A | 123.9 | N3—C18—C19 | 103.0 (2) |
C16—N4—H4A | 123.9 | N3—C18—H18A | 111.2 |
N1—C1—N2 | 114.6 (3) | C19—C18—H18A | 111.2 |
N1—C1—S1 | 132.6 (2) | N3—C18—H18B | 111.2 |
N2—C1—S1 | 112.79 (19) | C19—C18—H18B | 111.2 |
C3—C2—C7 | 119.1 (3) | H18A—C18—H18B | 109.1 |
C3—C2—N1 | 129.4 (3) | C20—C19—C18 | 116.3 (3) |
C7—C2—N1 | 111.5 (2) | C20—C19—C9 | 115.4 (2) |
C4—C3—C2 | 118.0 (3) | C18—C19—C9 | 104.1 (2) |
C4—C3—H3 | 121.0 | C20—C19—H19 | 106.8 |
C2—C3—H3 | 121.0 | C18—C19—H19 | 106.8 |
C3—C4—C5 | 121.8 (3) | C9—C19—H19 | 106.8 |
C3—C4—H4 | 119.1 | C25—C20—C21 | 116.4 (3) |
C5—C4—H4 | 119.1 | C25—C20—C19 | 122.5 (3) |
C4—C5—C6 | 121.5 (3) | C21—C20—C19 | 121.1 (3) |
C4—C5—H5 | 119.2 | C22—C21—C20 | 122.1 (4) |
C6—C5—H5 | 119.2 | C22—C21—Cl1 | 117.5 (3) |
C7—C6—C5 | 115.9 (3) | C20—C21—Cl1 | 120.3 (3) |
C7—C6—H6 | 122.1 | C23—C22—C21 | 119.6 (4) |
C5—C6—H6 | 122.1 | C23—C22—H22 | 120.2 |
C6—C7—C2 | 123.6 (3) | C21—C22—H22 | 120.2 |
C6—C7—N2 | 132.5 (3) | C24—C23—C22 | 119.9 (4) |
C2—C7—N2 | 103.9 (2) | C24—C23—H23 | 120.1 |
O1—C8—N2 | 124.5 (3) | C22—C23—H23 | 120.1 |
O1—C8—C9 | 125.4 (3) | C23—C24—C25 | 119.9 (4) |
N2—C8—C9 | 110.1 (2) | C23—C24—H24 | 120.0 |
C8—C9—C19 | 109.2 (2) | C25—C24—H24 | 120.0 |
C8—C9—C10 | 110.4 (2) | C24—C25—C20 | 122.0 (3) |
C19—C9—C10 | 104.2 (2) | C24—C25—H25 | 119.0 |
C8—C9—S1 | 106.99 (18) | C20—C25—H25 | 119.0 |
C19—C9—S1 | 114.48 (19) | N3—C26—H26A | 109.5 |
C10—C9—S1 | 111.47 (18) | N3—C26—H26B | 109.5 |
N3—C10—C11 | 113.4 (2) | H26A—C26—H26B | 109.5 |
N3—C10—C17 | 113.3 (2) | N3—C26—H26C | 109.5 |
C11—C10—C17 | 102.0 (2) | H26A—C26—H26C | 109.5 |
N3—C10—C9 | 101.1 (2) | H26B—C26—H26C | 109.5 |
C11—C10—C9 | 118.0 (2) | C28—O3—C27 | 110.5 (2) |
C17—C10—C9 | 109.4 (2) | O3—C27—C28i | 110.3 (2) |
C12—C11—C16 | 119.0 (3) | O3—C27—H27A | 109.6 |
C12—C11—C10 | 132.4 (3) | C28i—C27—H27A | 109.6 |
C16—C11—C10 | 108.5 (3) | O3—C27—H27B | 109.6 |
C11—C12—C13 | 118.9 (3) | C28i—C27—H27B | 109.6 |
C11—C12—H12 | 120.5 | H27A—C27—H27B | 108.1 |
C13—C12—H12 | 120.5 | O3—C28—C27i | 110.6 (3) |
C14—C13—C12 | 120.6 (3) | O3—C28—H28A | 109.5 |
C14—C13—H13 | 119.7 | C27i—C28—H28A | 109.5 |
C12—C13—H13 | 119.7 | O3—C28—H28B | 109.5 |
C15—C14—C13 | 121.3 (3) | C27i—C28—H28B | 109.5 |
C15—C14—H14 | 119.4 | H28A—C28—H28B | 108.1 |
C13—C14—H14 | 119.4 | ||
C2—N1—C1—N2 | 0.7 (3) | C17—C10—C11—C12 | −176.6 (3) |
C2—N1—C1—S1 | 179.7 (2) | C9—C10—C11—C12 | 63.5 (4) |
C8—N2—C1—N1 | 167.6 (2) | N3—C10—C11—C16 | 121.7 (2) |
C7—N2—C1—N1 | −0.7 (3) | C17—C10—C11—C16 | −0.5 (3) |
C8—N2—C1—S1 | −11.7 (3) | C9—C10—C11—C16 | −120.3 (3) |
C7—N2—C1—S1 | −179.92 (18) | C16—C11—C12—C13 | 1.6 (4) |
C9—S1—C1—N1 | −173.8 (3) | C10—C11—C12—C13 | 177.4 (3) |
C9—S1—C1—N2 | 5.2 (2) | C11—C12—C13—C14 | −1.6 (5) |
C1—N1—C2—C3 | 178.1 (3) | C12—C13—C14—C15 | 0.4 (5) |
C1—N1—C2—C7 | −0.5 (3) | C13—C14—C15—C16 | 0.6 (5) |
C7—C2—C3—C4 | 0.7 (4) | C14—C15—C16—C11 | −0.6 (4) |
N1—C2—C3—C4 | −177.8 (3) | C14—C15—C16—N4 | −177.7 (3) |
C2—C3—C4—C5 | 0.2 (4) | C12—C11—C16—C15 | −0.5 (4) |
C3—C4—C5—C6 | −1.0 (5) | C10—C11—C16—C15 | −177.3 (3) |
C4—C5—C6—C7 | 0.9 (4) | C12—C11—C16—N4 | 177.0 (2) |
C5—C6—C7—C2 | 0.0 (4) | C10—C11—C16—N4 | 0.3 (3) |
C5—C6—C7—N2 | 177.1 (3) | C17—N4—C16—C15 | 177.5 (3) |
C3—C2—C7—C6 | −0.8 (4) | C17—N4—C16—C11 | 0.1 (3) |
N1—C2—C7—C6 | 177.9 (3) | C16—N4—C17—O2 | 179.9 (3) |
C3—C2—C7—N2 | −178.6 (2) | C16—N4—C17—C10 | −0.4 (3) |
N1—C2—C7—N2 | 0.1 (3) | N3—C10—C17—O2 | 57.9 (4) |
C8—N2—C7—C6 | 17.7 (5) | C11—C10—C17—O2 | −179.8 (3) |
C1—N2—C7—C6 | −177.3 (3) | C9—C10—C17—O2 | −54.0 (4) |
C8—N2—C7—C2 | −164.8 (3) | N3—C10—C17—N4 | −121.7 (2) |
C1—N2—C7—C2 | 0.3 (3) | C11—C10—C17—N4 | 0.6 (3) |
C1—N2—C8—O1 | −166.1 (3) | C9—C10—C17—N4 | 126.3 (2) |
C7—N2—C8—O1 | −2.2 (5) | C26—N3—C18—C19 | −174.6 (2) |
C1—N2—C8—C9 | 12.5 (3) | C10—N3—C18—C19 | −46.2 (3) |
C7—N2—C8—C9 | 176.4 (3) | N3—C18—C19—C20 | 155.5 (2) |
O1—C8—C9—C19 | 46.5 (4) | N3—C18—C19—C9 | 27.4 (3) |
N2—C8—C9—C19 | −132.1 (2) | C8—C9—C19—C20 | 111.7 (3) |
O1—C8—C9—C10 | −67.6 (4) | C10—C9—C19—C20 | −130.2 (3) |
N2—C8—C9—C10 | 113.8 (2) | S1—C9—C19—C20 | −8.2 (3) |
O1—C8—C9—S1 | 170.9 (3) | C8—C9—C19—C18 | −119.7 (2) |
N2—C8—C9—S1 | −7.7 (3) | C10—C9—C19—C18 | −1.6 (3) |
C1—S1—C9—C8 | 1.42 (19) | S1—C9—C19—C18 | 120.4 (2) |
C1—S1—C9—C19 | 122.6 (2) | C18—C19—C20—C25 | −31.0 (4) |
C1—S1—C9—C10 | −119.41 (19) | C9—C19—C20—C25 | 91.3 (3) |
C26—N3—C10—C11 | −61.5 (3) | C18—C19—C20—C21 | 150.6 (3) |
C18—N3—C10—C11 | 171.5 (2) | C9—C19—C20—C21 | −87.1 (3) |
C26—N3—C10—C17 | 54.2 (3) | C25—C20—C21—C22 | 4.1 (5) |
C18—N3—C10—C17 | −72.8 (3) | C19—C20—C21—C22 | −177.4 (3) |
C26—N3—C10—C9 | 171.2 (2) | C25—C20—C21—Cl1 | −174.0 (2) |
C18—N3—C10—C9 | 44.1 (3) | C19—C20—C21—Cl1 | 4.5 (4) |
C8—C9—C10—N3 | 92.8 (2) | C20—C21—C22—C23 | −2.2 (6) |
C19—C9—C10—N3 | −24.5 (3) | Cl1—C21—C22—C23 | 176.0 (3) |
S1—C9—C10—N3 | −148.45 (18) | C21—C22—C23—C24 | −0.9 (6) |
C8—C9—C10—C11 | −31.6 (3) | C22—C23—C24—C25 | 1.8 (6) |
C19—C9—C10—C11 | −148.8 (2) | C23—C24—C25—C20 | 0.3 (5) |
S1—C9—C10—C11 | 87.2 (3) | C21—C20—C25—C24 | −3.1 (5) |
C8—C9—C10—C17 | −147.5 (2) | C19—C20—C25—C24 | 178.4 (3) |
C19—C9—C10—C17 | 95.3 (2) | C28—O3—C27—C28i | −57.3 (4) |
S1—C9—C10—C17 | −28.7 (3) | C27—O3—C28—C27i | 57.5 (4) |
N3—C10—C11—C12 | −54.4 (4) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C26H19ClN4O2S·0.5C4H8O2 |
Mr | 531.01 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 10.085 (3), 29.272 (9), 8.561 (3) |
β (°) | 99.287 (6) |
V (Å3) | 2494.2 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.18 × 0.16 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.924, 0.960 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14310, 5109, 2883 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.104, 1.02 |
No. of reflections | 5109 |
No. of parameters | 335 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.25 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
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Spiro compounds represent an important class of naturally occurring substances characterized by pronounced biological properties (Kobayashi et al., 1991; James et al., 1991). 1,3-Dipolar cycloaddition reactions are important process for the construction of spiro compounds (Caramella & Grunanger, 1984). In this paper, the structure of the title compound, (I) (Fig. 1), is reported.
There exists a dispiro ring in the molecule that consists of a 2-oxoindoline ring, a pyrrolidine ring and a benzo[4,5]imidazo[2,1-b]thiazol-3(2H)-one system. The pyrrolidine ring (N3/C9/C10/C18/C19) is not planar, having an envelope conformation. Half of a dioxane solvate molecule is found in the asymmetric unit.
Two molecules of (I) are connected by N—H···O hydrogen bonds to the dioxane solvate, with an N···O distance of 2.823 (2) Å and an N—H···O angle of 149.9 (3)°.