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The thiosemicarbazone molecule in C
10H
12N
6S
2·2C
3H
7NO has
symmetry. The thiosemicarbazone moiety and the benzene ring are essentially coplanar, with mean and maximum deviations of 0.03 and 0.11 Å, respectively. The dimethylformamide molecules bridge the thiosemicarbazone moieties, forming two-dimensional sheets through N—H
O hydrogen bonds.
Supporting information
CCDC reference: 153888
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1995); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Terephthaldehyde Thiosemicarbazone Bis-
N,
N-Dimethylformamide
top
Crystal data top
C10H12N6S2·2C3H7NO | F(000) = 904 |
Mr = 426.56 | Dx = 1.306 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 28.227 (6) Å | Cell parameters from 32 reflections |
b = 5.991 (3) Å | θ = 5.2–11.7° |
c = 12.873 (3) Å | µ = 0.27 mm−1 |
β = 94.753 (19)° | T = 293 K |
V = 2169.2 (14) Å3 | Block, yellow |
Z = 4 | 0.50 × 0.40 × 0.40 mm |
Data collection top
Bruker P4 diffractometer | 1578 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 25.0°, θmin = 2.9° |
ω/2θ scans | h = −1→33 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→7 |
Tmin = 0.817, Tmax = 0.938 | l = −15→15 |
2412 measured reflections | 3 standard reflections every 97 reflections |
1902 independent reflections | intensity decay: 9.1% |
Refinement top
Refinement on F2 | Secondary atom site location: dimap |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0519P)2 + 1.5245P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
1902 reflections | Δρmax = 0.18 e Å−3 |
130 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0036 (6) |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.35205 (2) | 0.36673 (11) | 0.07922 (4) | 0.0621 (2) | |
N2 | 0.40444 (6) | 0.5453 (3) | 0.23451 (12) | 0.0485 (4) | |
H2A | 0.3976 | 0.4289 | 0.2695 | 0.058* | |
N3 | 0.43213 (6) | 0.7111 (3) | 0.28144 (12) | 0.0446 (4) | |
C1 | 0.38788 (7) | 0.5650 (3) | 0.13336 (14) | 0.0439 (5) | |
C2 | 0.44279 (7) | 0.6859 (3) | 0.37899 (15) | 0.0437 (5) | |
H2B | 0.4318 | 0.5605 | 0.4122 | 0.052* | |
C3 | 0.47171 (6) | 0.8491 (3) | 0.43953 (14) | 0.0399 (4) | |
C4 | 0.48568 (7) | 0.8044 (3) | 0.54390 (15) | 0.0439 (5) | |
H4A | 0.4758 | 0.6731 | 0.5740 | 0.053* | |
C5 | 0.51387 (7) | 0.9517 (4) | 0.60303 (14) | 0.0439 (5) | |
H5A | 0.5233 | 0.9176 | 0.6721 | 0.053* | |
O1 | 0.36653 (6) | 0.2122 (3) | 0.36084 (11) | 0.0607 (4) | |
N1 | 0.40164 (7) | 0.7407 (3) | 0.08186 (13) | 0.0557 (5) | |
H1A | 0.4204 | 0.8372 | 0.1128 | 0.067* | |
H1B | 0.3918 | 0.7586 | 0.0174 | 0.067* | |
C6 | 0.34432 (8) | 0.0553 (4) | 0.31922 (16) | 0.0515 (5) | |
H6A | 0.3553 | −0.0029 | 0.2587 | 0.062* | |
C7 | 0.28523 (10) | −0.2362 (5) | 0.3057 (2) | 0.0790 (8) | |
H7A | 0.3002 | −0.2703 | 0.2433 | 0.118* | |
H7B | 0.2519 | −0.2121 | 0.2888 | 0.118* | |
H7C | 0.2896 | −0.3586 | 0.3537 | 0.118* | |
C8 | 0.28567 (9) | 0.0517 (5) | 0.44367 (18) | 0.0655 (7) | |
H8A | 0.2972 | 0.2005 | 0.4571 | 0.098* | |
H8B | 0.2945 | −0.0411 | 0.5030 | 0.098* | |
H8C | 0.2517 | 0.0545 | 0.4311 | 0.098* | |
N4 | 0.30630 (6) | −0.0372 (3) | 0.35294 (14) | 0.0504 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0673 (4) | 0.0664 (4) | 0.0499 (3) | −0.0247 (3) | −0.0115 (3) | −0.0082 (3) |
N2 | 0.0561 (10) | 0.0481 (10) | 0.0396 (9) | −0.0160 (8) | −0.0065 (7) | −0.0019 (7) |
N3 | 0.0439 (9) | 0.0478 (10) | 0.0408 (9) | −0.0097 (8) | −0.0036 (7) | −0.0069 (7) |
C1 | 0.0415 (10) | 0.0498 (12) | 0.0398 (10) | −0.0024 (9) | −0.0006 (8) | −0.0065 (9) |
C2 | 0.0450 (10) | 0.0447 (11) | 0.0405 (10) | −0.0057 (9) | −0.0019 (8) | −0.0027 (8) |
C3 | 0.0365 (9) | 0.0453 (11) | 0.0374 (9) | −0.0027 (8) | 0.0000 (7) | −0.0054 (8) |
C4 | 0.0465 (11) | 0.0442 (11) | 0.0402 (10) | −0.0070 (9) | −0.0006 (8) | 0.0014 (8) |
C5 | 0.0441 (10) | 0.0535 (12) | 0.0328 (9) | −0.0031 (9) | −0.0042 (8) | −0.0004 (8) |
O1 | 0.0712 (10) | 0.0615 (10) | 0.0481 (8) | −0.0182 (8) | −0.0019 (7) | −0.0005 (7) |
N1 | 0.0665 (12) | 0.0577 (12) | 0.0410 (9) | −0.0169 (9) | −0.0069 (8) | −0.0004 (8) |
C6 | 0.0566 (12) | 0.0524 (12) | 0.0445 (11) | 0.0028 (11) | −0.0016 (9) | −0.0007 (10) |
C7 | 0.0757 (18) | 0.0635 (17) | 0.095 (2) | −0.0135 (14) | −0.0060 (15) | −0.0126 (14) |
C8 | 0.0620 (14) | 0.0714 (16) | 0.0639 (14) | 0.0086 (13) | 0.0101 (11) | 0.0034 (12) |
N4 | 0.0514 (10) | 0.0440 (10) | 0.0549 (10) | 0.0012 (8) | −0.0007 (8) | −0.0011 (8) |
Geometric parameters (Å, º) top
S1—C1 | 1.674 (2) | O1—C6 | 1.228 (3) |
N2—C1 | 1.352 (2) | N1—H1A | 0.8600 |
N2—N3 | 1.373 (2) | N1—H1B | 0.8600 |
N2—H2A | 0.8600 | C6—N4 | 1.313 (3) |
N3—C2 | 1.276 (2) | C6—H6A | 0.9300 |
C1—N1 | 1.319 (3) | C7—N4 | 1.444 (3) |
C2—C3 | 1.457 (3) | C7—H7A | 0.9600 |
C2—H2B | 0.9300 | C7—H7B | 0.9600 |
C3—C5i | 1.388 (3) | C7—H7C | 0.9600 |
C3—C4 | 1.394 (3) | C8—N4 | 1.449 (3) |
C4—C5 | 1.375 (3) | C8—H8A | 0.9600 |
C4—H4A | 0.9300 | C8—H8B | 0.9600 |
C5—C3i | 1.388 (3) | C8—H8C | 0.9600 |
C5—H5A | 0.9300 | | |
| | | |
C1—N2—N3 | 119.96 (17) | C1—N1—H1B | 120.0 |
C1—N2—H2A | 120.0 | H1A—N1—H1B | 120.0 |
N3—N2—H2A | 120.0 | O1—C6—N4 | 125.5 (2) |
C2—N3—N2 | 115.25 (17) | O1—C6—H6A | 117.3 |
N1—C1—N2 | 117.45 (18) | N4—C6—H6A | 117.3 |
N1—C1—S1 | 123.34 (15) | N4—C7—H7A | 109.5 |
N2—C1—S1 | 119.20 (16) | N4—C7—H7B | 109.5 |
N3—C2—C3 | 121.53 (19) | H7A—C7—H7B | 109.5 |
N3—C2—H2B | 119.2 | N4—C7—H7C | 109.5 |
C3—C2—H2B | 119.2 | H7A—C7—H7C | 109.5 |
C5i—C3—C4 | 118.44 (18) | H7B—C7—H7C | 109.5 |
C5i—C3—C2 | 122.35 (17) | N4—C8—H8A | 109.5 |
C4—C3—C2 | 119.21 (18) | N4—C8—H8B | 109.5 |
C5—C4—C3 | 120.99 (19) | H8A—C8—H8B | 109.5 |
C5—C4—H4A | 119.5 | N4—C8—H8C | 109.5 |
C3—C4—H4A | 119.5 | H8A—C8—H8C | 109.5 |
C4—C5—C3i | 120.56 (18) | H8B—C8—H8C | 109.5 |
C4—C5—H5A | 119.7 | C6—N4—C7 | 121.9 (2) |
C3i—C5—H5A | 119.7 | C6—N4—C8 | 120.4 (2) |
C1—N1—H1A | 120.0 | C7—N4—C8 | 117.6 (2) |
Symmetry code: (i) −x+1, −y+2, −z+1. |
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