Terephthal­aldehyde bis­(thio­semi­carba­zone) bis­(di­methyl­form­amide) solvate

The thio­semicarbazone mol­ecule in C₁₀H₁₂N₆S₂·2C₃H₇NO 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.

Computing details

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

Crystal data

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) Å^3	Block, yellow
Z = 4	0.50 × 0.40 × 0.40 mm

Data collection

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

Refinement on F^2	Secondary atom site location: dimap
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0519P)^2 + 1.5245P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0036 (6)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C5^i	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—C3^i	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
C5^i—C3—C4	118.44 (18)	H7B—C7—H7C	109.5
C5^i—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—C3^i	120.56 (18)	H8B—C8—H8C	109.5
C4—C5—H5A	119.7	C6—N4—C7	121.9 (2)
C3^i—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.