Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703752X/at2357sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680703752X/at2357Isup2.hkl |
CCDC reference: 660214
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.130
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
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
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.
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).
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).
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.
C13H8N2O2S | F(000) = 1056 |
Mr = 256.27 | Dx = 1.456 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3262 reflections |
a = 8.4727 (15) Å | θ = 2.4–23.6° |
b = 21.327 (4) Å | µ = 0.27 mm−1 |
c = 12.942 (2) Å | T = 294 K |
β = 90.740 (3)° | Block, yellow |
V = 2338.4 (7) Å3 | 0.26 × 0.22 × 0.14 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 4790 independent reflections |
Radiation source: fine-focus sealed tube | 2978 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 26.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→10 |
Tmin = 0.933, Tmax = 0.963 | k = −26→20 |
13313 measured reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-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 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C13H8N2O2S | V = 2338.4 (7) Å3 |
Mr = 256.27 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.4727 (15) Å | µ = 0.27 mm−1 |
b = 21.327 (4) Å | T = 294 K |
c = 12.942 (2) Å | 0.26 × 0.22 × 0.14 mm |
β = 90.740 (3)° |
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 = 0.963 | Rint = 0.041 |
13313 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.20 e Å−3 |
4790 reflections | Δρmin = −0.38 e Å−3 |
325 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 | 0.31619 (9) | 0.53967 (3) | 0.74090 (5) | 0.0538 (2) | |
S2 | 0.32169 (10) | 0.27454 (4) | 0.82918 (6) | 0.0642 (2) | |
O1 | −0.0683 (2) | 0.36649 (9) | 0.76193 (13) | 0.0576 (5) | |
O2 | 0.1037 (3) | 0.38058 (10) | 0.42808 (14) | 0.0726 (6) | |
O3 | 0.5966 (2) | 0.43516 (8) | 1.03183 (13) | 0.0515 (5) | |
O4 | 0.7077 (2) | 0.46997 (8) | 0.68989 (12) | 0.0518 (5) | |
N1 | 0.1224 (2) | 0.44033 (9) | 0.63749 (15) | 0.0454 (5) | |
N2 | 0.0281 (2) | 0.39189 (9) | 0.59954 (14) | 0.0423 (5) | |
N3 | 0.5253 (2) | 0.38981 (9) | 0.83827 (15) | 0.0420 (5) | |
N4 | 0.6191 (2) | 0.44210 (8) | 0.85373 (14) | 0.0398 (5) | |
C1 | 0.4415 (3) | 0.59990 (12) | 0.7181 (2) | 0.0543 (7) | |
H1 | 0.4896 | 0.6235 | 0.7700 | 0.065* | |
C2 | 0.4635 (4) | 0.60972 (14) | 0.6173 (2) | 0.0721 (9) | |
H2 | 0.5293 | 0.6408 | 0.5918 | 0.087* | |
C3 | 0.3771 (4) | 0.56820 (13) | 0.5535 (2) | 0.0646 (8) | |
H3 | 0.3788 | 0.5688 | 0.4816 | 0.077* | |
C4 | 0.2893 (3) | 0.52645 (11) | 0.61120 (18) | 0.0436 (6) | |
C5 | 0.1893 (3) | 0.47651 (12) | 0.5731 (2) | 0.0487 (6) | |
H5 | 0.1740 | 0.4708 | 0.5024 | 0.058* | |
C6 | −0.0622 (3) | 0.35680 (11) | 0.67075 (18) | 0.0423 (6) | |
C7 | −0.1402 (3) | 0.30689 (11) | 0.60781 (18) | 0.0412 (6) | |
C8 | −0.2488 (3) | 0.26202 (12) | 0.6354 (2) | 0.0507 (7) | |
H8 | −0.2855 | 0.2592 | 0.7026 | 0.061* | |
C9 | −0.3011 (3) | 0.22104 (12) | 0.5587 (2) | 0.0563 (7) | |
H9 | −0.3761 | 0.1908 | 0.5747 | 0.068* | |
C10 | −0.2443 (3) | 0.22424 (13) | 0.4595 (2) | 0.0592 (7) | |
H10 | −0.2797 | 0.1956 | 0.4102 | 0.071* | |
C11 | −0.1353 (3) | 0.26951 (13) | 0.4323 (2) | 0.0582 (7) | |
H11 | −0.0965 | 0.2719 | 0.3656 | 0.070* | |
C12 | −0.0866 (3) | 0.31089 (12) | 0.50782 (18) | 0.0451 (6) | |
C13 | 0.0251 (3) | 0.36405 (12) | 0.50107 (19) | 0.0484 (6) | |
C14 | 0.2387 (4) | 0.22267 (14) | 0.7441 (2) | 0.0642 (8) | |
H14 | 0.1872 | 0.1862 | 0.7642 | 0.077* | |
C15 | 0.2556 (3) | 0.23996 (13) | 0.6455 (2) | 0.0589 (8) | |
H15 | 0.2173 | 0.2170 | 0.5894 | 0.071* | |
C16 | 0.3380 (3) | 0.29693 (13) | 0.6365 (2) | 0.0530 (7) | |
H16 | 0.3597 | 0.3159 | 0.5736 | 0.064* | |
C17 | 0.3828 (3) | 0.32148 (11) | 0.72955 (19) | 0.0447 (6) | |
C18 | 0.4755 (3) | 0.37733 (11) | 0.7475 (2) | 0.0468 (6) | |
H18 | 0.4987 | 0.4040 | 0.6929 | 0.056* | |
C19 | 0.6516 (3) | 0.46019 (11) | 0.95717 (18) | 0.0390 (6) | |
C20 | 0.7642 (3) | 0.51331 (10) | 0.94960 (17) | 0.0366 (5) | |
C21 | 0.8318 (3) | 0.54996 (11) | 1.02630 (18) | 0.0437 (6) | |
H21 | 0.8052 | 0.5448 | 1.0953 | 0.052* | |
C22 | 0.9408 (3) | 0.59478 (12) | 0.99646 (19) | 0.0475 (6) | |
H22 | 0.9880 | 0.6204 | 1.0462 | 0.057* | |
C23 | 0.9802 (3) | 0.60191 (11) | 0.89348 (19) | 0.0481 (6) | |
H23 | 1.0554 | 0.6317 | 0.8757 | 0.058* | |
C24 | 0.9107 (3) | 0.56591 (11) | 0.81649 (19) | 0.0443 (6) | |
H24 | 0.9363 | 0.5713 | 0.7474 | 0.053* | |
C25 | 0.8019 (3) | 0.52176 (10) | 0.84651 (17) | 0.0370 (5) | |
C26 | 0.7089 (3) | 0.47684 (11) | 0.78229 (18) | 0.0388 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0587 (4) | 0.0627 (5) | 0.0403 (4) | −0.0125 (4) | 0.0053 (3) | −0.0081 (3) |
S2 | 0.0822 (6) | 0.0567 (5) | 0.0536 (4) | −0.0137 (4) | −0.0037 (4) | 0.0069 (3) |
O1 | 0.0730 (13) | 0.0640 (12) | 0.0360 (10) | −0.0058 (10) | 0.0066 (9) | −0.0051 (8) |
O2 | 0.0948 (16) | 0.0811 (14) | 0.0423 (11) | −0.0369 (12) | 0.0186 (11) | −0.0133 (10) |
O3 | 0.0634 (12) | 0.0519 (11) | 0.0392 (10) | −0.0081 (9) | 0.0066 (9) | 0.0039 (8) |
O4 | 0.0648 (12) | 0.0578 (11) | 0.0328 (9) | −0.0057 (9) | −0.0019 (8) | −0.0012 (8) |
N1 | 0.0495 (13) | 0.0453 (12) | 0.0413 (12) | −0.0047 (10) | −0.0006 (10) | −0.0083 (10) |
N2 | 0.0486 (12) | 0.0445 (12) | 0.0337 (11) | −0.0069 (10) | 0.0005 (9) | −0.0068 (9) |
N3 | 0.0439 (12) | 0.0366 (11) | 0.0454 (12) | 0.0000 (9) | −0.0041 (9) | −0.0003 (9) |
N4 | 0.0464 (12) | 0.0354 (11) | 0.0374 (11) | −0.0027 (9) | 0.0002 (9) | −0.0022 (9) |
C1 | 0.0537 (17) | 0.0537 (16) | 0.0555 (17) | −0.0115 (14) | 0.0023 (13) | −0.0168 (13) |
C2 | 0.094 (3) | 0.068 (2) | 0.0545 (18) | −0.0365 (18) | 0.0124 (17) | 0.0001 (15) |
C3 | 0.096 (2) | 0.0636 (19) | 0.0345 (14) | −0.0246 (17) | −0.0010 (14) | −0.0025 (13) |
C4 | 0.0487 (15) | 0.0433 (14) | 0.0389 (13) | −0.0003 (12) | 0.0002 (11) | −0.0045 (11) |
C5 | 0.0578 (17) | 0.0480 (15) | 0.0401 (14) | −0.0042 (13) | −0.0053 (12) | −0.0059 (12) |
C6 | 0.0448 (15) | 0.0441 (14) | 0.0381 (14) | 0.0050 (12) | 0.0009 (11) | −0.0007 (11) |
C7 | 0.0393 (14) | 0.0414 (13) | 0.0428 (14) | 0.0042 (11) | −0.0012 (11) | −0.0007 (11) |
C8 | 0.0492 (16) | 0.0478 (16) | 0.0553 (16) | 0.0005 (13) | 0.0077 (13) | 0.0052 (13) |
C9 | 0.0492 (17) | 0.0403 (15) | 0.079 (2) | −0.0060 (13) | 0.0023 (15) | 0.0010 (14) |
C10 | 0.0607 (18) | 0.0518 (17) | 0.0649 (19) | −0.0060 (15) | −0.0091 (15) | −0.0127 (14) |
C11 | 0.0662 (19) | 0.0585 (18) | 0.0500 (16) | −0.0123 (15) | 0.0000 (14) | −0.0129 (13) |
C12 | 0.0466 (15) | 0.0461 (15) | 0.0427 (14) | −0.0027 (12) | 0.0002 (12) | −0.0044 (11) |
C13 | 0.0558 (17) | 0.0502 (16) | 0.0393 (14) | −0.0075 (13) | 0.0027 (12) | −0.0048 (12) |
C14 | 0.068 (2) | 0.0435 (16) | 0.080 (2) | −0.0117 (14) | −0.0046 (17) | −0.0002 (14) |
C15 | 0.0622 (19) | 0.0571 (18) | 0.0571 (18) | −0.0103 (15) | −0.0056 (14) | −0.0119 (14) |
C16 | 0.0582 (17) | 0.0543 (16) | 0.0465 (15) | −0.0106 (14) | −0.0013 (13) | −0.0039 (13) |
C17 | 0.0411 (14) | 0.0422 (14) | 0.0507 (15) | 0.0021 (12) | −0.0004 (12) | 0.0012 (12) |
C18 | 0.0542 (16) | 0.0405 (14) | 0.0457 (15) | −0.0039 (12) | −0.0018 (12) | 0.0043 (11) |
C19 | 0.0435 (14) | 0.0372 (13) | 0.0363 (13) | 0.0053 (11) | 0.0001 (11) | −0.0005 (10) |
C20 | 0.0385 (13) | 0.0332 (12) | 0.0381 (12) | 0.0051 (11) | 0.0005 (10) | 0.0007 (10) |
C21 | 0.0527 (16) | 0.0424 (14) | 0.0359 (13) | 0.0025 (12) | 0.0031 (11) | −0.0011 (11) |
C22 | 0.0543 (16) | 0.0416 (14) | 0.0463 (15) | −0.0002 (13) | −0.0057 (12) | −0.0048 (12) |
C23 | 0.0492 (16) | 0.0412 (14) | 0.0540 (16) | −0.0052 (12) | 0.0009 (13) | 0.0056 (12) |
C24 | 0.0484 (15) | 0.0461 (15) | 0.0385 (13) | 0.0019 (12) | 0.0029 (12) | 0.0062 (11) |
C25 | 0.0408 (14) | 0.0346 (12) | 0.0355 (12) | 0.0060 (11) | −0.0007 (10) | 0.0017 (10) |
C26 | 0.0414 (14) | 0.0386 (13) | 0.0364 (13) | 0.0056 (11) | −0.0022 (11) | 0.0022 (11) |
S1—C1 | 1.695 (3) | C8—H8 | 0.9300 |
S1—C4 | 1.715 (2) | C9—C10 | 1.379 (4) |
S2—C14 | 1.706 (3) | C9—H9 | 0.9300 |
S2—C17 | 1.718 (2) | C10—C11 | 1.385 (4) |
O1—C6 | 1.200 (3) | C10—H10 | 0.9300 |
O2—C13 | 1.215 (3) | C11—C12 | 1.376 (3) |
O3—C19 | 1.203 (3) | C11—H11 | 0.9300 |
O4—C26 | 1.205 (3) | C12—C13 | 1.480 (3) |
N1—C5 | 1.274 (3) | C14—C15 | 1.338 (4) |
N1—N2 | 1.392 (3) | C14—H14 | 0.9300 |
N2—C13 | 1.406 (3) | C15—C16 | 1.407 (4) |
N2—C6 | 1.418 (3) | C15—H15 | 0.9300 |
N3—C18 | 1.272 (3) | C16—C17 | 1.362 (3) |
N3—N4 | 1.383 (3) | C16—H16 | 0.9300 |
N4—C26 | 1.415 (3) | C17—C18 | 1.444 (3) |
N4—C19 | 1.417 (3) | C18—H18 | 0.9300 |
C1—C2 | 1.337 (3) | C19—C20 | 1.485 (3) |
C1—H1 | 0.9300 | C20—C21 | 1.382 (3) |
C2—C3 | 1.409 (4) | C20—C25 | 1.388 (3) |
C2—H2 | 0.9300 | C21—C22 | 1.387 (3) |
C3—C4 | 1.385 (4) | C21—H21 | 0.9300 |
C3—H3 | 0.9300 | C22—C23 | 1.387 (3) |
C4—C5 | 1.443 (3) | C22—H22 | 0.9300 |
C5—H5 | 0.9300 | C23—C24 | 1.384 (3) |
C6—C7 | 1.490 (3) | C23—H23 | 0.9300 |
C7—C8 | 1.377 (3) | C24—C25 | 1.377 (3) |
C7—C12 | 1.380 (3) | C24—H24 | 0.9300 |
C8—C9 | 1.391 (4) | C25—C26 | 1.487 (3) |
C1—S1—C4 | 91.71 (12) | C11—C12—C13 | 129.5 (2) |
C14—S2—C17 | 91.10 (14) | C7—C12—C13 | 108.7 (2) |
C5—N1—N2 | 118.5 (2) | O2—C13—N2 | 125.3 (2) |
N1—N2—C13 | 129.58 (19) | O2—C13—C12 | 128.7 (2) |
N1—N2—C6 | 118.30 (18) | N2—C13—C12 | 105.9 (2) |
C13—N2—C6 | 111.26 (19) | C15—C14—S2 | 112.9 (2) |
C18—N3—N4 | 119.1 (2) | C15—C14—H14 | 123.6 |
N3—N4—C26 | 129.87 (19) | S2—C14—H14 | 123.6 |
N3—N4—C19 | 117.42 (18) | C14—C15—C16 | 112.1 (2) |
C26—N4—C19 | 112.06 (19) | C14—C15—H15 | 124.0 |
C2—C1—S1 | 112.6 (2) | C16—C15—H15 | 124.0 |
C2—C1—H1 | 123.7 | C17—C16—C15 | 113.1 (2) |
S1—C1—H1 | 123.7 | C17—C16—H16 | 123.5 |
C1—C2—C3 | 113.3 (3) | C15—C16—H16 | 123.5 |
C1—C2—H2 | 123.4 | C16—C17—C18 | 127.1 (2) |
C3—C2—H2 | 123.4 | C16—C17—S2 | 110.86 (19) |
C4—C3—C2 | 111.5 (2) | C18—C17—S2 | 121.93 (19) |
C4—C3—H3 | 124.3 | N3—C18—C17 | 119.6 (2) |
C2—C3—H3 | 124.3 | N3—C18—H18 | 120.2 |
C3—C4—C5 | 127.4 (2) | C17—C18—H18 | 120.2 |
C3—C4—S1 | 110.90 (19) | O3—C19—N4 | 124.5 (2) |
C5—C4—S1 | 121.72 (19) | O3—C19—C20 | 130.3 (2) |
N1—C5—C4 | 119.2 (2) | N4—C19—C20 | 105.21 (19) |
N1—C5—H5 | 120.4 | C21—C20—C25 | 121.3 (2) |
C4—C5—H5 | 120.4 | C21—C20—C19 | 130.1 (2) |
O1—C6—N2 | 125.3 (2) | C25—C20—C19 | 108.6 (2) |
O1—C6—C7 | 129.5 (2) | C20—C21—C22 | 117.4 (2) |
N2—C6—C7 | 105.12 (19) | C20—C21—H21 | 121.3 |
C8—C7—C12 | 121.0 (2) | C22—C21—H21 | 121.3 |
C8—C7—C6 | 130.4 (2) | C23—C22—C21 | 120.8 (2) |
C12—C7—C6 | 108.6 (2) | C23—C22—H22 | 119.6 |
C7—C8—C9 | 117.4 (2) | C21—C22—H22 | 119.6 |
C7—C8—H8 | 121.3 | C24—C23—C22 | 121.7 (2) |
C9—C8—H8 | 121.3 | C24—C23—H23 | 119.1 |
C10—C9—C8 | 121.4 (3) | C22—C23—H23 | 119.1 |
C10—C9—H9 | 119.3 | C25—C24—C23 | 117.2 (2) |
C8—C9—H9 | 119.3 | C25—C24—H24 | 121.4 |
C9—C10—C11 | 120.9 (3) | C23—C24—H24 | 121.4 |
C9—C10—H10 | 119.6 | C24—C25—C20 | 121.6 (2) |
C11—C10—H10 | 119.6 | C24—C25—C26 | 129.4 (2) |
C12—C11—C10 | 117.5 (3) | C20—C25—C26 | 109.1 (2) |
C12—C11—H11 | 121.2 | O4—C26—N4 | 126.0 (2) |
C10—C11—H11 | 121.2 | O4—C26—C25 | 129.1 (2) |
C11—C12—C7 | 121.8 (2) | N4—C26—C25 | 104.93 (19) |
C5—N1—N2—C13 | 19.7 (4) | C11—C12—C13—N2 | 178.0 (3) |
C5—N1—N2—C6 | −172.0 (2) | C7—C12—C13—N2 | −2.4 (3) |
C18—N3—N4—C26 | −19.8 (3) | C17—S2—C14—C15 | −0.2 (2) |
C18—N3—N4—C19 | 170.2 (2) | S2—C14—C15—C16 | 0.0 (3) |
C4—S1—C1—C2 | −0.4 (3) | C14—C15—C16—C17 | 0.3 (4) |
S1—C1—C2—C3 | 0.4 (4) | C15—C16—C17—C18 | 176.6 (2) |
C1—C2—C3—C4 | −0.2 (4) | C15—C16—C17—S2 | −0.5 (3) |
C2—C3—C4—C5 | −178.6 (3) | C14—S2—C17—C16 | 0.4 (2) |
C2—C3—C4—S1 | −0.1 (3) | C14—S2—C17—C18 | −176.8 (2) |
C1—S1—C4—C3 | 0.2 (2) | N4—N3—C18—C17 | 177.5 (2) |
C1—S1—C4—C5 | 178.9 (2) | C16—C17—C18—N3 | −170.8 (3) |
N2—N1—C5—C4 | −179.2 (2) | S2—C17—C18—N3 | 6.0 (3) |
C3—C4—C5—N1 | 176.7 (3) | N3—N4—C19—O3 | −4.0 (3) |
S1—C4—C5—N1 | −1.8 (4) | C26—N4—C19—O3 | −175.7 (2) |
N1—N2—C6—O1 | 2.4 (4) | N3—N4—C19—C20 | 175.23 (18) |
C13—N2—C6—O1 | 172.8 (2) | C26—N4—C19—C20 | 3.5 (2) |
N1—N2—C6—C7 | −176.46 (19) | O3—C19—C20—C21 | −2.8 (4) |
C13—N2—C6—C7 | −6.1 (3) | N4—C19—C20—C21 | 178.0 (2) |
O1—C6—C7—C8 | 5.7 (5) | O3—C19—C20—C25 | 175.2 (2) |
N2—C6—C7—C8 | −175.5 (2) | N4—C19—C20—C25 | −4.0 (2) |
O1—C6—C7—C12 | −174.4 (3) | C25—C20—C21—C22 | −1.1 (4) |
N2—C6—C7—C12 | 4.4 (3) | C19—C20—C21—C22 | 176.7 (2) |
C12—C7—C8—C9 | 0.2 (4) | C20—C21—C22—C23 | −0.3 (4) |
C6—C7—C8—C9 | −179.9 (2) | C21—C22—C23—C24 | 1.4 (4) |
C7—C8—C9—C10 | 1.4 (4) | C22—C23—C24—C25 | −1.0 (4) |
C8—C9—C10—C11 | −1.4 (4) | C23—C24—C25—C20 | −0.5 (3) |
C9—C10—C11—C12 | −0.1 (4) | C23—C24—C25—C26 | 180.0 (2) |
C10—C11—C12—C7 | 1.7 (4) | C21—C20—C25—C24 | 1.5 (4) |
C10—C11—C12—C13 | −178.9 (3) | C19—C20—C25—C24 | −176.7 (2) |
C8—C7—C12—C11 | −1.8 (4) | C21—C20—C25—C26 | −178.8 (2) |
C6—C7—C12—C11 | 178.3 (2) | C19—C20—C25—C26 | 3.0 (3) |
C8—C7—C12—C13 | 178.7 (2) | N3—N4—C26—O4 | 7.5 (4) |
C6—C7—C12—C13 | −1.2 (3) | C19—N4—C26—O4 | 177.9 (2) |
N1—N2—C13—O2 | −3.6 (4) | N3—N4—C26—C25 | −172.2 (2) |
C6—N2—C13—O2 | −172.6 (3) | C19—N4—C26—C25 | −1.8 (2) |
N1—N2—C13—C12 | 174.4 (2) | C24—C25—C26—O4 | −0.9 (4) |
C6—N2—C13—C12 | 5.4 (3) | C20—C25—C26—O4 | 179.4 (2) |
C11—C12—C13—O2 | −4.0 (5) | C24—C25—C26—N4 | 178.8 (2) |
C7—C12—C13—O2 | 175.5 (3) | C20—C25—C26—N4 | −0.9 (2) |
Experimental details
Crystal data | |
Chemical formula | C13H8N2O2S |
Mr | 256.27 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 8.4727 (15), 21.327 (4), 12.942 (2) |
β (°) | 90.740 (3) |
V (Å3) | 2338.4 (7) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.26 × 0.22 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.933, 0.963 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13313, 4790, 2978 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.130, 1.00 |
No. of reflections | 4790 |
No. of parameters | 325 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.38 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
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.