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The title compound, C26H19ClN4O2S·0.5C4H8O2, was synthesized by the intermolecular [3 + 2]-cyclo­addition of azomethine yl­ide, derived from isatin and sarcosine by a de­carboxyl­ative route, and 2-(2-chloro­benzyl­idene)­benzo­[4,5]­imidazo­[2,1-b]­thia­zol-3-one. In the mol­ecule, the two spiro junctions link a planar 2-oxoindoline ring, a pyrrolidine ring in an envelope conformation, and a planar benzo­[4,5]­imidazo­[2,1-b]­thia­zol-3(2H)-one ring. Two mol­ecules are connected by N—H...O hydrogen bonds to a molecule of dioxane on an inversion center, with an N...O distance of 2.823 (2) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017471/ww6108sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017471/ww6108Isup2.hkl
Contains datablock I

CCDC reference: 222865

Key indicators

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

Comment top

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)°.

Experimental top

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 (CN) 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.

Refinement top

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).

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme, drawn with 30% probability ellipsoids.
[Figure 2] Fig. 2. The crystal packing diagram of (I), viewed along the c axis.
(I) top
Crystal data top
C26H19ClN4O2S·0.5C4H8O2F(000) = 1104
Mr = 531.01Dx = 1.414 Mg m3
Monoclinic, P21/cMelting point = 516–518 K
Hall symbol: P 2ycMo Kα radiation, λ = 0.71073 Å
a = 10.085 (3) ÅCell parameters from 911 reflections
b = 29.272 (9) Åθ = 2.5–24.6°
c = 8.561 (3) ŵ = 0.28 mm1
β = 99.287 (6)°T = 293 K
V = 2494.2 (13) Å3Block, colorless
Z = 40.18 × 0.16 × 0.14 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
5109 independent reflections
Radiation source: fine-focus sealed tube2883 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
ϕ and ω scansθmax = 26.4°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1112
Tmin = 0.924, Tmax = 0.960k = 3634
14310 measured reflectionsl = 810
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-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 = 1.02Δρmax = 0.21 e Å3
5109 reflectionsΔρmin = 0.25 e Å3
335 parameters
Crystal data top
C26H19ClN4O2S·0.5C4H8O2V = 2494.2 (13) Å3
Mr = 531.01Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.085 (3) ŵ = 0.28 mm1
b = 29.272 (9) ÅT = 293 K
c = 8.561 (3) Å0.18 × 0.16 × 0.14 mm
β = 99.287 (6)°
Data collection top
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 = 0.960Rint = 0.069
14310 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 1.02Δρmax = 0.21 e Å3
5109 reflectionsΔρmin = 0.25 e Å3
335 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
S11.01570 (8)0.39685 (2)0.34987 (9)0.0404 (2)
Cl11.30898 (10)0.32301 (4)0.20570 (14)0.0859 (4)
N11.1313 (2)0.46458 (8)0.1893 (3)0.0376 (6)
N21.0369 (2)0.40382 (7)0.0521 (3)0.0330 (6)
N30.8000 (2)0.28879 (7)0.1905 (3)0.0378 (6)
N40.6542 (2)0.38362 (8)0.3273 (3)0.0417 (6)
H4A0.61210.39670.39470.050*
O10.9865 (2)0.33312 (6)0.0522 (3)0.0517 (6)
O20.8068 (2)0.34352 (7)0.5018 (2)0.0513 (6)
C11.0680 (3)0.42630 (9)0.1956 (3)0.0324 (7)
C21.1430 (3)0.46887 (9)0.0279 (4)0.0351 (7)
C31.1987 (3)0.50387 (9)0.0488 (4)0.0420 (8)
H31.23860.52890.00700.050*
C41.1934 (3)0.50051 (10)0.2097 (4)0.0474 (8)
H41.23070.52370.26300.057*
C51.1342 (3)0.46354 (10)0.2948 (4)0.0485 (8)
H51.13130.46280.40390.058*
C61.0791 (3)0.42766 (10)0.2212 (4)0.0436 (8)
H61.04030.40250.27730.052*
C71.0853 (3)0.43153 (9)0.0604 (3)0.0335 (7)
C80.9940 (3)0.35917 (10)0.0562 (4)0.0361 (7)
C90.9609 (3)0.34780 (9)0.2211 (3)0.0323 (7)
C100.8051 (3)0.33848 (9)0.2113 (3)0.0328 (7)
C110.7090 (3)0.36394 (9)0.0873 (3)0.0338 (7)
C120.6905 (3)0.36362 (10)0.0752 (4)0.0485 (8)
H120.74560.34600.12870.058*
C130.5880 (4)0.39006 (12)0.1585 (4)0.0605 (10)
H130.57590.39070.26850.073*
C140.5045 (4)0.41522 (12)0.0798 (5)0.0628 (10)
H140.43620.43250.13760.075*
C150.5199 (3)0.41535 (11)0.0826 (4)0.0545 (9)
H150.46280.43220.13570.065*
C160.6226 (3)0.38978 (9)0.1635 (4)0.0382 (7)
C170.7593 (3)0.35461 (9)0.3676 (4)0.0359 (7)
C180.9113 (3)0.27005 (9)0.3026 (4)0.0435 (8)
H18A0.92870.23850.27780.052*
H18B0.89310.27180.41020.052*
C191.0293 (3)0.30089 (9)0.2795 (4)0.0388 (7)
H191.06770.28820.19070.047*
C201.1425 (3)0.30421 (9)0.4177 (4)0.0447 (8)
C211.2738 (3)0.31241 (11)0.3947 (5)0.0571 (10)
C221.3798 (4)0.31379 (13)0.5190 (6)0.0770 (13)
H221.46700.31830.49960.092*
C231.3557 (4)0.30847 (13)0.6715 (6)0.0797 (13)
H231.42670.30900.75560.096*
C241.2267 (4)0.30243 (11)0.6994 (5)0.0672 (11)
H241.20990.29970.80260.081*
C251.1218 (3)0.30045 (11)0.5738 (4)0.0555 (9)
H251.03470.29650.59440.067*
C260.6711 (3)0.26742 (10)0.2007 (4)0.0563 (9)
H26A0.65200.27040.30650.084*
H26B0.67470.23560.17410.084*
H26C0.60160.28210.12810.084*
O30.5433 (2)0.45487 (7)0.4872 (3)0.0491 (6)
C270.6258 (3)0.48761 (11)0.5810 (4)0.0492 (9)
H27A0.71970.48060.58020.059*
H27B0.60970.48610.68960.059*
C280.4045 (3)0.46540 (10)0.4825 (4)0.0488 (8)
H28A0.38220.46330.58820.059*
H28B0.35000.44340.41590.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0556 (5)0.0336 (4)0.0317 (4)0.0061 (4)0.0059 (4)0.0020 (4)
Cl10.0537 (6)0.1073 (8)0.1049 (9)0.0045 (6)0.0371 (6)0.0248 (7)
N10.0379 (14)0.0294 (13)0.0432 (16)0.0076 (11)0.0001 (12)0.0011 (12)
N20.0401 (14)0.0265 (13)0.0321 (14)0.0070 (11)0.0053 (11)0.0023 (11)
N30.0351 (14)0.0267 (13)0.0527 (17)0.0030 (11)0.0103 (13)0.0001 (12)
N40.0422 (15)0.0438 (15)0.0412 (16)0.0086 (12)0.0132 (12)0.0007 (13)
O10.0804 (16)0.0337 (12)0.0476 (14)0.0175 (11)0.0310 (12)0.0132 (11)
O20.0594 (14)0.0593 (14)0.0353 (13)0.0141 (12)0.0081 (11)0.0074 (11)
C10.0307 (16)0.0283 (16)0.0359 (17)0.0024 (13)0.0015 (13)0.0010 (14)
C20.0304 (16)0.0319 (17)0.0424 (19)0.0023 (13)0.0038 (14)0.0020 (15)
C30.0372 (18)0.0291 (17)0.060 (2)0.0073 (14)0.0075 (16)0.0025 (16)
C40.049 (2)0.0372 (19)0.059 (2)0.0070 (16)0.0192 (17)0.0089 (17)
C50.060 (2)0.0444 (19)0.044 (2)0.0063 (17)0.0193 (17)0.0039 (17)
C60.056 (2)0.0368 (17)0.0403 (19)0.0106 (16)0.0161 (16)0.0033 (15)
C70.0359 (16)0.0248 (15)0.0406 (18)0.0023 (13)0.0084 (14)0.0011 (14)
C80.0366 (17)0.0310 (17)0.0421 (19)0.0051 (14)0.0111 (15)0.0040 (15)
C90.0400 (17)0.0237 (15)0.0346 (17)0.0024 (13)0.0099 (14)0.0017 (13)
C100.0377 (16)0.0290 (16)0.0326 (17)0.0003 (13)0.0086 (13)0.0020 (13)
C110.0383 (17)0.0260 (15)0.0356 (18)0.0041 (13)0.0015 (14)0.0016 (14)
C120.058 (2)0.0418 (19)0.044 (2)0.0094 (17)0.0046 (17)0.0015 (17)
C130.071 (3)0.059 (2)0.044 (2)0.016 (2)0.014 (2)0.0172 (19)
C140.054 (2)0.060 (2)0.069 (3)0.0013 (19)0.008 (2)0.018 (2)
C150.044 (2)0.050 (2)0.068 (3)0.0083 (17)0.0037 (18)0.0130 (19)
C160.0357 (17)0.0336 (17)0.0438 (19)0.0020 (15)0.0022 (15)0.0043 (15)
C170.0376 (18)0.0320 (17)0.0385 (19)0.0005 (14)0.0076 (15)0.0052 (15)
C180.0431 (19)0.0304 (16)0.060 (2)0.0026 (15)0.0184 (17)0.0068 (16)
C190.0393 (17)0.0282 (16)0.052 (2)0.0045 (14)0.0179 (16)0.0060 (15)
C200.0369 (18)0.0296 (17)0.068 (2)0.0051 (14)0.0095 (17)0.0112 (17)
C210.043 (2)0.048 (2)0.082 (3)0.0035 (17)0.014 (2)0.015 (2)
C220.044 (2)0.066 (3)0.118 (4)0.002 (2)0.005 (3)0.019 (3)
C230.057 (3)0.071 (3)0.100 (4)0.007 (2)0.018 (3)0.016 (3)
C240.070 (3)0.058 (2)0.068 (3)0.003 (2)0.006 (2)0.014 (2)
C250.047 (2)0.054 (2)0.065 (3)0.0052 (17)0.0097 (19)0.017 (2)
C260.048 (2)0.046 (2)0.074 (3)0.0126 (17)0.0107 (18)0.0006 (19)
O30.0402 (13)0.0480 (13)0.0569 (15)0.0064 (11)0.0018 (11)0.0116 (11)
C270.0374 (19)0.055 (2)0.053 (2)0.0019 (16)0.0014 (16)0.0045 (18)
C280.0406 (19)0.049 (2)0.055 (2)0.0014 (16)0.0042 (16)0.0027 (18)
Geometric parameters (Å, º) top
S1—C11.730 (3)C12—H120.9300
S1—C91.840 (3)C13—C141.375 (5)
Cl1—C211.740 (4)C13—H130.9300
N1—C11.295 (3)C14—C151.374 (5)
N1—C21.411 (4)C14—H140.9300
N2—C81.379 (3)C15—C161.372 (4)
N2—C11.384 (3)C15—H150.9300
N2—C71.406 (3)C18—C191.532 (4)
N3—C261.458 (3)C18—H18A0.9700
N3—C181.461 (3)C18—H18B0.9700
N3—C101.465 (3)C19—C201.509 (4)
N4—C171.358 (3)C19—H190.9800
N4—C161.399 (3)C20—C251.390 (4)
N4—H4A0.8600C20—C211.390 (4)
O1—C81.194 (3)C21—C221.382 (5)
O2—C171.216 (3)C22—C231.375 (5)
C2—C31.384 (4)C22—H220.9300
C2—C71.401 (4)C23—C241.371 (5)
C3—C41.374 (4)C23—H230.9300
C3—H30.9300C24—C251.383 (4)
C4—C51.385 (4)C24—H240.9300
C4—H40.9300C25—H250.9300
C5—C61.387 (4)C26—H26A0.9600
C5—H50.9300C26—H26B0.9600
C6—C71.372 (4)C26—H26C0.9600
C6—H60.9300O3—C281.427 (3)
C8—C91.539 (4)O3—C271.428 (3)
C9—C191.582 (4)C27—C28i1.492 (4)
C9—C101.583 (4)C27—H27A0.9700
C10—C111.513 (4)C27—H27B0.9700
C10—C171.558 (4)C28—C27i1.492 (4)
C11—C121.374 (4)C28—H28A0.9700
C11—C161.393 (4)C28—H28B0.9700
C12—C131.393 (4)
C1—S1—C991.76 (13)C16—C15—C14117.6 (3)
C1—N1—C2103.7 (2)C16—C15—H15121.2
C8—N2—C1117.1 (2)C14—C15—H15121.2
C8—N2—C7135.2 (2)C15—C16—C11122.6 (3)
C1—N2—C7106.3 (2)C15—C16—N4127.4 (3)
C26—N3—C18113.4 (2)C11—C16—N4109.9 (3)
C26—N3—C10115.6 (2)O2—C17—N4125.4 (3)
C18—N3—C10106.5 (2)O2—C17—C10127.2 (3)
C17—N4—C16112.2 (2)N4—C17—C10107.4 (2)
C17—N4—H4A123.9N3—C18—C19103.0 (2)
C16—N4—H4A123.9N3—C18—H18A111.2
N1—C1—N2114.6 (3)C19—C18—H18A111.2
N1—C1—S1132.6 (2)N3—C18—H18B111.2
N2—C1—S1112.79 (19)C19—C18—H18B111.2
C3—C2—C7119.1 (3)H18A—C18—H18B109.1
C3—C2—N1129.4 (3)C20—C19—C18116.3 (3)
C7—C2—N1111.5 (2)C20—C19—C9115.4 (2)
C4—C3—C2118.0 (3)C18—C19—C9104.1 (2)
C4—C3—H3121.0C20—C19—H19106.8
C2—C3—H3121.0C18—C19—H19106.8
C3—C4—C5121.8 (3)C9—C19—H19106.8
C3—C4—H4119.1C25—C20—C21116.4 (3)
C5—C4—H4119.1C25—C20—C19122.5 (3)
C4—C5—C6121.5 (3)C21—C20—C19121.1 (3)
C4—C5—H5119.2C22—C21—C20122.1 (4)
C6—C5—H5119.2C22—C21—Cl1117.5 (3)
C7—C6—C5115.9 (3)C20—C21—Cl1120.3 (3)
C7—C6—H6122.1C23—C22—C21119.6 (4)
C5—C6—H6122.1C23—C22—H22120.2
C6—C7—C2123.6 (3)C21—C22—H22120.2
C6—C7—N2132.5 (3)C24—C23—C22119.9 (4)
C2—C7—N2103.9 (2)C24—C23—H23120.1
O1—C8—N2124.5 (3)C22—C23—H23120.1
O1—C8—C9125.4 (3)C23—C24—C25119.9 (4)
N2—C8—C9110.1 (2)C23—C24—H24120.0
C8—C9—C19109.2 (2)C25—C24—H24120.0
C8—C9—C10110.4 (2)C24—C25—C20122.0 (3)
C19—C9—C10104.2 (2)C24—C25—H25119.0
C8—C9—S1106.99 (18)C20—C25—H25119.0
C19—C9—S1114.48 (19)N3—C26—H26A109.5
C10—C9—S1111.47 (18)N3—C26—H26B109.5
N3—C10—C11113.4 (2)H26A—C26—H26B109.5
N3—C10—C17113.3 (2)N3—C26—H26C109.5
C11—C10—C17102.0 (2)H26A—C26—H26C109.5
N3—C10—C9101.1 (2)H26B—C26—H26C109.5
C11—C10—C9118.0 (2)C28—O3—C27110.5 (2)
C17—C10—C9109.4 (2)O3—C27—C28i110.3 (2)
C12—C11—C16119.0 (3)O3—C27—H27A109.6
C12—C11—C10132.4 (3)C28i—C27—H27A109.6
C16—C11—C10108.5 (3)O3—C27—H27B109.6
C11—C12—C13118.9 (3)C28i—C27—H27B109.6
C11—C12—H12120.5H27A—C27—H27B108.1
C13—C12—H12120.5O3—C28—C27i110.6 (3)
C14—C13—C12120.6 (3)O3—C28—H28A109.5
C14—C13—H13119.7C27i—C28—H28A109.5
C12—C13—H13119.7O3—C28—H28B109.5
C15—C14—C13121.3 (3)C27i—C28—H28B109.5
C15—C14—H14119.4H28A—C28—H28B108.1
C13—C14—H14119.4
C2—N1—C1—N20.7 (3)C17—C10—C11—C12176.6 (3)
C2—N1—C1—S1179.7 (2)C9—C10—C11—C1263.5 (4)
C8—N2—C1—N1167.6 (2)N3—C10—C11—C16121.7 (2)
C7—N2—C1—N10.7 (3)C17—C10—C11—C160.5 (3)
C8—N2—C1—S111.7 (3)C9—C10—C11—C16120.3 (3)
C7—N2—C1—S1179.92 (18)C16—C11—C12—C131.6 (4)
C9—S1—C1—N1173.8 (3)C10—C11—C12—C13177.4 (3)
C9—S1—C1—N25.2 (2)C11—C12—C13—C141.6 (5)
C1—N1—C2—C3178.1 (3)C12—C13—C14—C150.4 (5)
C1—N1—C2—C70.5 (3)C13—C14—C15—C160.6 (5)
C7—C2—C3—C40.7 (4)C14—C15—C16—C110.6 (4)
N1—C2—C3—C4177.8 (3)C14—C15—C16—N4177.7 (3)
C2—C3—C4—C50.2 (4)C12—C11—C16—C150.5 (4)
C3—C4—C5—C61.0 (5)C10—C11—C16—C15177.3 (3)
C4—C5—C6—C70.9 (4)C12—C11—C16—N4177.0 (2)
C5—C6—C7—C20.0 (4)C10—C11—C16—N40.3 (3)
C5—C6—C7—N2177.1 (3)C17—N4—C16—C15177.5 (3)
C3—C2—C7—C60.8 (4)C17—N4—C16—C110.1 (3)
N1—C2—C7—C6177.9 (3)C16—N4—C17—O2179.9 (3)
C3—C2—C7—N2178.6 (2)C16—N4—C17—C100.4 (3)
N1—C2—C7—N20.1 (3)N3—C10—C17—O257.9 (4)
C8—N2—C7—C617.7 (5)C11—C10—C17—O2179.8 (3)
C1—N2—C7—C6177.3 (3)C9—C10—C17—O254.0 (4)
C8—N2—C7—C2164.8 (3)N3—C10—C17—N4121.7 (2)
C1—N2—C7—C20.3 (3)C11—C10—C17—N40.6 (3)
C1—N2—C8—O1166.1 (3)C9—C10—C17—N4126.3 (2)
C7—N2—C8—O12.2 (5)C26—N3—C18—C19174.6 (2)
C1—N2—C8—C912.5 (3)C10—N3—C18—C1946.2 (3)
C7—N2—C8—C9176.4 (3)N3—C18—C19—C20155.5 (2)
O1—C8—C9—C1946.5 (4)N3—C18—C19—C927.4 (3)
N2—C8—C9—C19132.1 (2)C8—C9—C19—C20111.7 (3)
O1—C8—C9—C1067.6 (4)C10—C9—C19—C20130.2 (3)
N2—C8—C9—C10113.8 (2)S1—C9—C19—C208.2 (3)
O1—C8—C9—S1170.9 (3)C8—C9—C19—C18119.7 (2)
N2—C8—C9—S17.7 (3)C10—C9—C19—C181.6 (3)
C1—S1—C9—C81.42 (19)S1—C9—C19—C18120.4 (2)
C1—S1—C9—C19122.6 (2)C18—C19—C20—C2531.0 (4)
C1—S1—C9—C10119.41 (19)C9—C19—C20—C2591.3 (3)
C26—N3—C10—C1161.5 (3)C18—C19—C20—C21150.6 (3)
C18—N3—C10—C11171.5 (2)C9—C19—C20—C2187.1 (3)
C26—N3—C10—C1754.2 (3)C25—C20—C21—C224.1 (5)
C18—N3—C10—C1772.8 (3)C19—C20—C21—C22177.4 (3)
C26—N3—C10—C9171.2 (2)C25—C20—C21—Cl1174.0 (2)
C18—N3—C10—C944.1 (3)C19—C20—C21—Cl14.5 (4)
C8—C9—C10—N392.8 (2)C20—C21—C22—C232.2 (6)
C19—C9—C10—N324.5 (3)Cl1—C21—C22—C23176.0 (3)
S1—C9—C10—N3148.45 (18)C21—C22—C23—C240.9 (6)
C8—C9—C10—C1131.6 (3)C22—C23—C24—C251.8 (6)
C19—C9—C10—C11148.8 (2)C23—C24—C25—C200.3 (5)
S1—C9—C10—C1187.2 (3)C21—C20—C25—C243.1 (5)
C8—C9—C10—C17147.5 (2)C19—C20—C25—C24178.4 (3)
C19—C9—C10—C1795.3 (2)C28—O3—C27—C28i57.3 (4)
S1—C9—C10—C1728.7 (3)C27—O3—C28—C27i57.5 (4)
N3—C10—C11—C1254.4 (4)
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC26H19ClN4O2S·0.5C4H8O2
Mr531.01
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)10.085 (3), 29.272 (9), 8.561 (3)
β (°) 99.287 (6)
V3)2494.2 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.18 × 0.16 × 0.14
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.924, 0.960
No. of measured, independent and
observed [I > 2σ(I)] reflections
14310, 5109, 2883
Rint0.069
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.104, 1.02
No. of reflections5109
No. of parameters335
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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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