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The asymmetric unit of the title compound, C13H8N2O2S, contains two independent mol­ecules. The thiophene ring is planar [r.m.s. deviation = 0.0015 (5) Å]. The r.m.s. deviation for the isoindoline group is 0.0195 (4) Å. The dihedral angle between the two planes is 12.9 (2)°. The crystal structure is stabilized by weak inter­molecular inter­actions to form a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703752X/at2357sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680703752X/at2357Isup2.hkl
Contains datablock I

CCDC reference: 660214

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.047
  • wR factor = 0.130
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C14 - C15 .. 5.18 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al.,2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound, (I).

In the molecular structure of the compound (I) (Fig. 1), the geometric parameters are normal. In one molecule of the unit, the thiophen ring (C1—C4/S1) is approximately planar, with a maximum deviation from the mean plane of 0.0015 (5) Å for atom S1, as the isoindoline group (C6—C13/N2) is approximately planar, with a maximum deviation from the mean plane of 0.0195 (4) Å for atom N2. The dihedral angle between these two planes is12.9(1)°. In the other molecule of the unit, the thiophen ring (C14—C17/S2) is approximately planar, with a maximum deviation from the mean plane of 0.0019 (2) Å for atom S2, as the isoindoline group (C19—C26/N4) is approximately planar, with a maximum deviation from the mean plane of 0.0187 (4) Å for atom N4. The dihedral angle between these two planes is14.2(3)°. The molecular structure stabilized by the weak intermolecular interactions to form a three-dimensional network, as illustraed in Fig.2.

Related literature top

For general background, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).

Experimental top

An anhydrous ethanol solution (50 ml) of thiophene-2-carbaldehyde (1.12 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of N-Amino-phthalimide (1.52 g, 10 mmol), and the mixture was stirred at 350 K for 6 h under N2, whereupon a yellow precipitate appeared. The product was isolated, recrystallized from anhydrous ethanol and then dried in vacuo to give pure compound (I) in 79% yield. Yellows single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an anhydrous ethanol solution.

Refinement top

The H atoms were included in calculated positions, with C—H = 0.93 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Structure description top

In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al.,2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound, (I).

In the molecular structure of the compound (I) (Fig. 1), the geometric parameters are normal. In one molecule of the unit, the thiophen ring (C1—C4/S1) is approximately planar, with a maximum deviation from the mean plane of 0.0015 (5) Å for atom S1, as the isoindoline group (C6—C13/N2) is approximately planar, with a maximum deviation from the mean plane of 0.0195 (4) Å for atom N2. The dihedral angle between these two planes is12.9(1)°. In the other molecule of the unit, the thiophen ring (C14—C17/S2) is approximately planar, with a maximum deviation from the mean plane of 0.0019 (2) Å for atom S2, as the isoindoline group (C19—C26/N4) is approximately planar, with a maximum deviation from the mean plane of 0.0187 (4) Å for atom N4. The dihedral angle between these two planes is14.2(3)°. The molecular structure stabilized by the weak intermolecular interactions to form a three-dimensional network, as illustraed in Fig.2.

For general background, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; 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). Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of (I), viwed down the b axis. Hydrogen bonds are indicated by dashed lines.
2-(2-Thienylmethyleneamino)isoindoline-1,3-dione top
Crystal data top
C13H8N2O2SF(000) = 1056
Mr = 256.27Dx = 1.456 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3262 reflections
a = 8.4727 (15) Åθ = 2.4–23.6°
b = 21.327 (4) ŵ = 0.27 mm1
c = 12.942 (2) ÅT = 294 K
β = 90.740 (3)°Block, yellow
V = 2338.4 (7) Å30.26 × 0.22 × 0.14 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
4790 independent reflections
Radiation source: fine-focus sealed tube2978 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 810
Tmin = 0.933, Tmax = 0.963k = 2620
13313 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0628P)2 + 0.4001P]
where P = (Fo2 + 2Fc2)/3
4790 reflections(Δ/σ)max = 0.001
325 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
C13H8N2O2SV = 2338.4 (7) Å3
Mr = 256.27Z = 8
Monoclinic, P21/cMo Kα radiation
a = 8.4727 (15) ŵ = 0.27 mm1
b = 21.327 (4) ÅT = 294 K
c = 12.942 (2) Å0.26 × 0.22 × 0.14 mm
β = 90.740 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
4790 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2978 reflections with I > 2σ(I)
Tmin = 0.933, Tmax = 0.963Rint = 0.041
13313 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 1.00Δρmax = 0.20 e Å3
4790 reflectionsΔρmin = 0.38 e Å3
325 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
S10.31619 (9)0.53967 (3)0.74090 (5)0.0538 (2)
S20.32169 (10)0.27454 (4)0.82918 (6)0.0642 (2)
O10.0683 (2)0.36649 (9)0.76193 (13)0.0576 (5)
O20.1037 (3)0.38058 (10)0.42808 (14)0.0726 (6)
O30.5966 (2)0.43516 (8)1.03183 (13)0.0515 (5)
O40.7077 (2)0.46997 (8)0.68989 (12)0.0518 (5)
N10.1224 (2)0.44033 (9)0.63749 (15)0.0454 (5)
N20.0281 (2)0.39189 (9)0.59954 (14)0.0423 (5)
N30.5253 (2)0.38981 (9)0.83827 (15)0.0420 (5)
N40.6191 (2)0.44210 (8)0.85373 (14)0.0398 (5)
C10.4415 (3)0.59990 (12)0.7181 (2)0.0543 (7)
H10.48960.62350.77000.065*
C20.4635 (4)0.60972 (14)0.6173 (2)0.0721 (9)
H20.52930.64080.59180.087*
C30.3771 (4)0.56820 (13)0.5535 (2)0.0646 (8)
H30.37880.56880.48160.077*
C40.2893 (3)0.52645 (11)0.61120 (18)0.0436 (6)
C50.1893 (3)0.47651 (12)0.5731 (2)0.0487 (6)
H50.17400.47080.50240.058*
C60.0622 (3)0.35680 (11)0.67075 (18)0.0423 (6)
C70.1402 (3)0.30689 (11)0.60781 (18)0.0412 (6)
C80.2488 (3)0.26202 (12)0.6354 (2)0.0507 (7)
H80.28550.25920.70260.061*
C90.3011 (3)0.22104 (12)0.5587 (2)0.0563 (7)
H90.37610.19080.57470.068*
C100.2443 (3)0.22424 (13)0.4595 (2)0.0592 (7)
H100.27970.19560.41020.071*
C110.1353 (3)0.26951 (13)0.4323 (2)0.0582 (7)
H110.09650.27190.36560.070*
C120.0866 (3)0.31089 (12)0.50782 (18)0.0451 (6)
C130.0251 (3)0.36405 (12)0.50107 (19)0.0484 (6)
C140.2387 (4)0.22267 (14)0.7441 (2)0.0642 (8)
H140.18720.18620.76420.077*
C150.2556 (3)0.23996 (13)0.6455 (2)0.0589 (8)
H150.21730.21700.58940.071*
C160.3380 (3)0.29693 (13)0.6365 (2)0.0530 (7)
H160.35970.31590.57360.064*
C170.3828 (3)0.32148 (11)0.72955 (19)0.0447 (6)
C180.4755 (3)0.37733 (11)0.7475 (2)0.0468 (6)
H180.49870.40400.69290.056*
C190.6516 (3)0.46019 (11)0.95717 (18)0.0390 (6)
C200.7642 (3)0.51331 (10)0.94960 (17)0.0366 (5)
C210.8318 (3)0.54996 (11)1.02630 (18)0.0437 (6)
H210.80520.54481.09530.052*
C220.9408 (3)0.59478 (12)0.99646 (19)0.0475 (6)
H220.98800.62041.04620.057*
C230.9802 (3)0.60191 (11)0.89348 (19)0.0481 (6)
H231.05540.63170.87570.058*
C240.9107 (3)0.56591 (11)0.81649 (19)0.0443 (6)
H240.93630.57130.74740.053*
C250.8019 (3)0.52176 (10)0.84651 (17)0.0370 (5)
C260.7089 (3)0.47684 (11)0.78229 (18)0.0388 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0587 (4)0.0627 (5)0.0403 (4)0.0125 (4)0.0053 (3)0.0081 (3)
S20.0822 (6)0.0567 (5)0.0536 (4)0.0137 (4)0.0037 (4)0.0069 (3)
O10.0730 (13)0.0640 (12)0.0360 (10)0.0058 (10)0.0066 (9)0.0051 (8)
O20.0948 (16)0.0811 (14)0.0423 (11)0.0369 (12)0.0186 (11)0.0133 (10)
O30.0634 (12)0.0519 (11)0.0392 (10)0.0081 (9)0.0066 (9)0.0039 (8)
O40.0648 (12)0.0578 (11)0.0328 (9)0.0057 (9)0.0019 (8)0.0012 (8)
N10.0495 (13)0.0453 (12)0.0413 (12)0.0047 (10)0.0006 (10)0.0083 (10)
N20.0486 (12)0.0445 (12)0.0337 (11)0.0069 (10)0.0005 (9)0.0068 (9)
N30.0439 (12)0.0366 (11)0.0454 (12)0.0000 (9)0.0041 (9)0.0003 (9)
N40.0464 (12)0.0354 (11)0.0374 (11)0.0027 (9)0.0002 (9)0.0022 (9)
C10.0537 (17)0.0537 (16)0.0555 (17)0.0115 (14)0.0023 (13)0.0168 (13)
C20.094 (3)0.068 (2)0.0545 (18)0.0365 (18)0.0124 (17)0.0001 (15)
C30.096 (2)0.0636 (19)0.0345 (14)0.0246 (17)0.0010 (14)0.0025 (13)
C40.0487 (15)0.0433 (14)0.0389 (13)0.0003 (12)0.0002 (11)0.0045 (11)
C50.0578 (17)0.0480 (15)0.0401 (14)0.0042 (13)0.0053 (12)0.0059 (12)
C60.0448 (15)0.0441 (14)0.0381 (14)0.0050 (12)0.0009 (11)0.0007 (11)
C70.0393 (14)0.0414 (13)0.0428 (14)0.0042 (11)0.0012 (11)0.0007 (11)
C80.0492 (16)0.0478 (16)0.0553 (16)0.0005 (13)0.0077 (13)0.0052 (13)
C90.0492 (17)0.0403 (15)0.079 (2)0.0060 (13)0.0023 (15)0.0010 (14)
C100.0607 (18)0.0518 (17)0.0649 (19)0.0060 (15)0.0091 (15)0.0127 (14)
C110.0662 (19)0.0585 (18)0.0500 (16)0.0123 (15)0.0000 (14)0.0129 (13)
C120.0466 (15)0.0461 (15)0.0427 (14)0.0027 (12)0.0002 (12)0.0044 (11)
C130.0558 (17)0.0502 (16)0.0393 (14)0.0075 (13)0.0027 (12)0.0048 (12)
C140.068 (2)0.0435 (16)0.080 (2)0.0117 (14)0.0046 (17)0.0002 (14)
C150.0622 (19)0.0571 (18)0.0571 (18)0.0103 (15)0.0056 (14)0.0119 (14)
C160.0582 (17)0.0543 (16)0.0465 (15)0.0106 (14)0.0013 (13)0.0039 (13)
C170.0411 (14)0.0422 (14)0.0507 (15)0.0021 (12)0.0004 (12)0.0012 (12)
C180.0542 (16)0.0405 (14)0.0457 (15)0.0039 (12)0.0018 (12)0.0043 (11)
C190.0435 (14)0.0372 (13)0.0363 (13)0.0053 (11)0.0001 (11)0.0005 (10)
C200.0385 (13)0.0332 (12)0.0381 (12)0.0051 (11)0.0005 (10)0.0007 (10)
C210.0527 (16)0.0424 (14)0.0359 (13)0.0025 (12)0.0031 (11)0.0011 (11)
C220.0543 (16)0.0416 (14)0.0463 (15)0.0002 (13)0.0057 (12)0.0048 (12)
C230.0492 (16)0.0412 (14)0.0540 (16)0.0052 (12)0.0009 (13)0.0056 (12)
C240.0484 (15)0.0461 (15)0.0385 (13)0.0019 (12)0.0029 (12)0.0062 (11)
C250.0408 (14)0.0346 (12)0.0355 (12)0.0060 (11)0.0007 (10)0.0017 (10)
C260.0414 (14)0.0386 (13)0.0364 (13)0.0056 (11)0.0022 (11)0.0022 (11)
Geometric parameters (Å, º) top
S1—C11.695 (3)C8—H80.9300
S1—C41.715 (2)C9—C101.379 (4)
S2—C141.706 (3)C9—H90.9300
S2—C171.718 (2)C10—C111.385 (4)
O1—C61.200 (3)C10—H100.9300
O2—C131.215 (3)C11—C121.376 (3)
O3—C191.203 (3)C11—H110.9300
O4—C261.205 (3)C12—C131.480 (3)
N1—C51.274 (3)C14—C151.338 (4)
N1—N21.392 (3)C14—H140.9300
N2—C131.406 (3)C15—C161.407 (4)
N2—C61.418 (3)C15—H150.9300
N3—C181.272 (3)C16—C171.362 (3)
N3—N41.383 (3)C16—H160.9300
N4—C261.415 (3)C17—C181.444 (3)
N4—C191.417 (3)C18—H180.9300
C1—C21.337 (3)C19—C201.485 (3)
C1—H10.9300C20—C211.382 (3)
C2—C31.409 (4)C20—C251.388 (3)
C2—H20.9300C21—C221.387 (3)
C3—C41.385 (4)C21—H210.9300
C3—H30.9300C22—C231.387 (3)
C4—C51.443 (3)C22—H220.9300
C5—H50.9300C23—C241.384 (3)
C6—C71.490 (3)C23—H230.9300
C7—C81.377 (3)C24—C251.377 (3)
C7—C121.380 (3)C24—H240.9300
C8—C91.391 (4)C25—C261.487 (3)
C1—S1—C491.71 (12)C11—C12—C13129.5 (2)
C14—S2—C1791.10 (14)C7—C12—C13108.7 (2)
C5—N1—N2118.5 (2)O2—C13—N2125.3 (2)
N1—N2—C13129.58 (19)O2—C13—C12128.7 (2)
N1—N2—C6118.30 (18)N2—C13—C12105.9 (2)
C13—N2—C6111.26 (19)C15—C14—S2112.9 (2)
C18—N3—N4119.1 (2)C15—C14—H14123.6
N3—N4—C26129.87 (19)S2—C14—H14123.6
N3—N4—C19117.42 (18)C14—C15—C16112.1 (2)
C26—N4—C19112.06 (19)C14—C15—H15124.0
C2—C1—S1112.6 (2)C16—C15—H15124.0
C2—C1—H1123.7C17—C16—C15113.1 (2)
S1—C1—H1123.7C17—C16—H16123.5
C1—C2—C3113.3 (3)C15—C16—H16123.5
C1—C2—H2123.4C16—C17—C18127.1 (2)
C3—C2—H2123.4C16—C17—S2110.86 (19)
C4—C3—C2111.5 (2)C18—C17—S2121.93 (19)
C4—C3—H3124.3N3—C18—C17119.6 (2)
C2—C3—H3124.3N3—C18—H18120.2
C3—C4—C5127.4 (2)C17—C18—H18120.2
C3—C4—S1110.90 (19)O3—C19—N4124.5 (2)
C5—C4—S1121.72 (19)O3—C19—C20130.3 (2)
N1—C5—C4119.2 (2)N4—C19—C20105.21 (19)
N1—C5—H5120.4C21—C20—C25121.3 (2)
C4—C5—H5120.4C21—C20—C19130.1 (2)
O1—C6—N2125.3 (2)C25—C20—C19108.6 (2)
O1—C6—C7129.5 (2)C20—C21—C22117.4 (2)
N2—C6—C7105.12 (19)C20—C21—H21121.3
C8—C7—C12121.0 (2)C22—C21—H21121.3
C8—C7—C6130.4 (2)C23—C22—C21120.8 (2)
C12—C7—C6108.6 (2)C23—C22—H22119.6
C7—C8—C9117.4 (2)C21—C22—H22119.6
C7—C8—H8121.3C24—C23—C22121.7 (2)
C9—C8—H8121.3C24—C23—H23119.1
C10—C9—C8121.4 (3)C22—C23—H23119.1
C10—C9—H9119.3C25—C24—C23117.2 (2)
C8—C9—H9119.3C25—C24—H24121.4
C9—C10—C11120.9 (3)C23—C24—H24121.4
C9—C10—H10119.6C24—C25—C20121.6 (2)
C11—C10—H10119.6C24—C25—C26129.4 (2)
C12—C11—C10117.5 (3)C20—C25—C26109.1 (2)
C12—C11—H11121.2O4—C26—N4126.0 (2)
C10—C11—H11121.2O4—C26—C25129.1 (2)
C11—C12—C7121.8 (2)N4—C26—C25104.93 (19)
C5—N1—N2—C1319.7 (4)C11—C12—C13—N2178.0 (3)
C5—N1—N2—C6172.0 (2)C7—C12—C13—N22.4 (3)
C18—N3—N4—C2619.8 (3)C17—S2—C14—C150.2 (2)
C18—N3—N4—C19170.2 (2)S2—C14—C15—C160.0 (3)
C4—S1—C1—C20.4 (3)C14—C15—C16—C170.3 (4)
S1—C1—C2—C30.4 (4)C15—C16—C17—C18176.6 (2)
C1—C2—C3—C40.2 (4)C15—C16—C17—S20.5 (3)
C2—C3—C4—C5178.6 (3)C14—S2—C17—C160.4 (2)
C2—C3—C4—S10.1 (3)C14—S2—C17—C18176.8 (2)
C1—S1—C4—C30.2 (2)N4—N3—C18—C17177.5 (2)
C1—S1—C4—C5178.9 (2)C16—C17—C18—N3170.8 (3)
N2—N1—C5—C4179.2 (2)S2—C17—C18—N36.0 (3)
C3—C4—C5—N1176.7 (3)N3—N4—C19—O34.0 (3)
S1—C4—C5—N11.8 (4)C26—N4—C19—O3175.7 (2)
N1—N2—C6—O12.4 (4)N3—N4—C19—C20175.23 (18)
C13—N2—C6—O1172.8 (2)C26—N4—C19—C203.5 (2)
N1—N2—C6—C7176.46 (19)O3—C19—C20—C212.8 (4)
C13—N2—C6—C76.1 (3)N4—C19—C20—C21178.0 (2)
O1—C6—C7—C85.7 (5)O3—C19—C20—C25175.2 (2)
N2—C6—C7—C8175.5 (2)N4—C19—C20—C254.0 (2)
O1—C6—C7—C12174.4 (3)C25—C20—C21—C221.1 (4)
N2—C6—C7—C124.4 (3)C19—C20—C21—C22176.7 (2)
C12—C7—C8—C90.2 (4)C20—C21—C22—C230.3 (4)
C6—C7—C8—C9179.9 (2)C21—C22—C23—C241.4 (4)
C7—C8—C9—C101.4 (4)C22—C23—C24—C251.0 (4)
C8—C9—C10—C111.4 (4)C23—C24—C25—C200.5 (3)
C9—C10—C11—C120.1 (4)C23—C24—C25—C26180.0 (2)
C10—C11—C12—C71.7 (4)C21—C20—C25—C241.5 (4)
C10—C11—C12—C13178.9 (3)C19—C20—C25—C24176.7 (2)
C8—C7—C12—C111.8 (4)C21—C20—C25—C26178.8 (2)
C6—C7—C12—C11178.3 (2)C19—C20—C25—C263.0 (3)
C8—C7—C12—C13178.7 (2)N3—N4—C26—O47.5 (4)
C6—C7—C12—C131.2 (3)C19—N4—C26—O4177.9 (2)
N1—N2—C13—O23.6 (4)N3—N4—C26—C25172.2 (2)
C6—N2—C13—O2172.6 (3)C19—N4—C26—C251.8 (2)
N1—N2—C13—C12174.4 (2)C24—C25—C26—O40.9 (4)
C6—N2—C13—C125.4 (3)C20—C25—C26—O4179.4 (2)
C11—C12—C13—O24.0 (5)C24—C25—C26—N4178.8 (2)
C7—C12—C13—O2175.5 (3)C20—C25—C26—N40.9 (2)

Experimental details

Crystal data
Chemical formulaC13H8N2O2S
Mr256.27
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)8.4727 (15), 21.327 (4), 12.942 (2)
β (°) 90.740 (3)
V3)2338.4 (7)
Z8
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.26 × 0.22 × 0.14
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.933, 0.963
No. of measured, independent and
observed [I > 2σ(I)] reflections
13313, 4790, 2978
Rint0.041
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.130, 1.00
No. of reflections4790
No. of parameters325
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.38

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

 

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