The title compound, C
16H
18N
4S
2, has a crystallographic inversion centre at the mid-point of the central C—C bond. The plane of the dithiooxamide fragment is approximately perpendicular to the plane of the dimethylene bridge [dihedral angle = 84.8 (1)°], the plane of which is in turn normal to the pyridine ring plane [dihedral angle = 89.80 (8)°]. An intermolecular N—H
N hydrogen bond involving the amide NH group and the pyridine N atom [N
N = 3.0503 (18) Å and N—H
N = 145.8 (14)°] links the molecules into chains extending along the
c axis.
Supporting information
CCDC reference: 274673
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.033
- wR factor = 0.097
- Data-to-parameter ratio = 19.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C1_a ... 1.53 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
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.
N,
N'-Bis[2-(2-pyridyl)ethyl]dithiooxamide
top
Crystal data top
C16H18N4S2 | F(000) = 348 |
Mr = 330.46 | Dx = 1.317 Mg m−3 |
Monoclinic, P21/c | Melting point: 431 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.4499 (18) Å | Cell parameters from 1570 reflections |
b = 6.0036 (10) Å | θ = 3.2–27.1° |
c = 13.688 (2) Å | µ = 0.32 mm−1 |
β = 103.995 (2)° | T = 293 K |
V = 833.2 (2) Å3 | Prism, orange |
Z = 2 | 0.28 × 0.24 × 0.20 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1982 independent reflections |
Radiation source: fine-focus sealed tube | 1491 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
φ and ω scans | θmax = 27.9°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→10 |
Tmin = 0.902, Tmax = 0.938 | k = −7→7 |
5351 measured reflections | l = −15→18 |
Refinement top
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0729P)2] where P = (Fo2 + 2Fc2)/3 |
1982 reflections | (Δ/σ)max = 0.001 |
104 parameters | Δρmax = 0.23 e Å−3 |
1 restraint | Δρmin = −0.16 e Å−3 |
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 | 0.30318 (3) | 0.09765 (7) | 0.42197 (3) | 0.05277 (16) | |
N1 | 0.46642 (11) | 0.16109 (19) | 0.59916 (9) | 0.0403 (3) | |
H1 | 0.5424 (11) | 0.141 (3) | 0.6385 (11) | 0.056 (5)* | |
N2 | 0.30448 (12) | 0.7694 (2) | 0.72214 (10) | 0.0503 (3) | |
C1 | 0.44296 (12) | 0.06969 (19) | 0.50958 (10) | 0.0356 (3) | |
C2 | 0.37278 (14) | 0.2993 (2) | 0.63434 (11) | 0.0437 (3) | |
H2A | 0.3924 | 0.2933 | 0.7073 | 0.052* | |
H2B | 0.2846 | 0.2405 | 0.6085 | 0.052* | |
C3 | 0.37657 (14) | 0.5402 (2) | 0.60114 (12) | 0.0461 (3) | |
H3A | 0.4625 | 0.6033 | 0.6311 | 0.055* | |
H3B | 0.3630 | 0.5462 | 0.5285 | 0.055* | |
C4 | 0.27215 (13) | 0.6746 (2) | 0.63203 (11) | 0.0399 (3) | |
C5 | 0.14701 (16) | 0.6912 (3) | 0.57051 (14) | 0.0617 (5) | |
H5 | 0.1270 | 0.6231 | 0.5076 | 0.074* | |
C6 | 0.05234 (18) | 0.8081 (4) | 0.60222 (17) | 0.0759 (6) | |
H6 | −0.0326 | 0.8199 | 0.5614 | 0.091* | |
C7 | 0.0841 (2) | 0.9072 (3) | 0.69443 (18) | 0.0729 (6) | |
H7 | 0.0219 | 0.9883 | 0.7180 | 0.087* | |
C8 | 0.2103 (2) | 0.8837 (3) | 0.75128 (15) | 0.0655 (5) | |
H8 | 0.2320 | 0.9515 | 0.8142 | 0.079* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0328 (2) | 0.0628 (3) | 0.0586 (3) | 0.01218 (16) | 0.00298 (16) | −0.00587 (18) |
N1 | 0.0330 (6) | 0.0444 (6) | 0.0436 (7) | 0.0098 (5) | 0.0097 (5) | 0.0023 (5) |
N2 | 0.0498 (7) | 0.0495 (7) | 0.0517 (8) | 0.0011 (6) | 0.0122 (6) | −0.0042 (6) |
C1 | 0.0306 (6) | 0.0334 (6) | 0.0449 (8) | 0.0036 (5) | 0.0130 (5) | 0.0060 (5) |
C2 | 0.0427 (8) | 0.0462 (8) | 0.0461 (8) | 0.0087 (6) | 0.0182 (6) | 0.0028 (6) |
C3 | 0.0408 (8) | 0.0430 (7) | 0.0579 (9) | 0.0006 (6) | 0.0188 (7) | −0.0017 (7) |
C4 | 0.0373 (7) | 0.0354 (6) | 0.0479 (8) | 0.0002 (5) | 0.0122 (6) | 0.0031 (6) |
C5 | 0.0434 (9) | 0.0779 (12) | 0.0601 (10) | 0.0040 (8) | 0.0054 (7) | −0.0067 (9) |
C6 | 0.0430 (9) | 0.0908 (14) | 0.0930 (15) | 0.0183 (9) | 0.0149 (9) | 0.0142 (12) |
C7 | 0.0679 (12) | 0.0573 (10) | 0.1074 (17) | 0.0218 (9) | 0.0487 (12) | 0.0080 (10) |
C8 | 0.0809 (13) | 0.0541 (9) | 0.0695 (12) | 0.0027 (9) | 0.0334 (10) | −0.0110 (8) |
Geometric parameters (Å, º) top
S1—C1 | 1.6591 (13) | C3—H3A | 0.9700 |
N1—C1 | 1.3112 (18) | C3—H3B | 0.9700 |
N1—C2 | 1.4511 (17) | C4—C5 | 1.377 (2) |
N1—H1 | 0.853 (9) | C5—C6 | 1.367 (3) |
N2—C4 | 1.3256 (19) | C5—H5 | 0.9300 |
N2—C8 | 1.338 (2) | C6—C7 | 1.362 (3) |
C1—C1i | 1.530 (2) | C6—H6 | 0.9300 |
C2—C3 | 1.520 (2) | C7—C8 | 1.366 (3) |
C2—H2A | 0.9700 | C7—H7 | 0.9300 |
C2—H2B | 0.9700 | C8—H8 | 0.9300 |
C3—C4 | 1.498 (2) | | |
| | | |
C1—N1—C2 | 124.12 (12) | C2—C3—H3B | 109.5 |
C1—N1—H1 | 117.7 (11) | H3A—C3—H3B | 108.1 |
C2—N1—H1 | 118.2 (11) | N2—C4—C5 | 121.91 (14) |
C4—N2—C8 | 117.21 (14) | N2—C4—C3 | 117.04 (13) |
N1—C1—C1i | 114.32 (14) | C5—C4—C3 | 121.01 (13) |
N1—C1—S1 | 124.50 (10) | C6—C5—C4 | 119.75 (17) |
C1i—C1—S1 | 121.18 (13) | C6—C5—H5 | 120.1 |
N1—C2—C3 | 112.12 (12) | C4—C5—H5 | 120.1 |
N1—C2—H2A | 109.2 | C7—C6—C5 | 119.06 (17) |
C3—C2—H2A | 109.2 | C7—C6—H6 | 120.5 |
N1—C2—H2B | 109.2 | C5—C6—H6 | 120.5 |
C3—C2—H2B | 109.2 | C6—C7—C8 | 117.93 (17) |
H2A—C2—H2B | 107.9 | C6—C7—H7 | 121.0 |
C4—C3—C2 | 110.79 (12) | C8—C7—H7 | 121.0 |
C4—C3—H3A | 109.5 | N2—C8—C7 | 124.15 (18) |
C2—C3—H3A | 109.5 | N2—C8—H8 | 117.9 |
C4—C3—H3B | 109.5 | C7—C8—H8 | 117.9 |
| | | |
C2—N1—C1—C1i | −179.72 (13) | C2—C3—C4—C5 | −88.52 (18) |
C2—N1—C1—S1 | 0.23 (19) | N2—C4—C5—C6 | 0.0 (3) |
C1—N1—C2—C3 | −84.01 (17) | C3—C4—C5—C6 | 177.57 (16) |
N1—C2—C3—C4 | 175.80 (12) | C4—C5—C6—C7 | 0.3 (3) |
C8—N2—C4—C5 | −0.3 (2) | C5—C6—C7—C8 | −0.2 (3) |
C8—N2—C4—C3 | −177.96 (13) | C4—N2—C8—C7 | 0.3 (3) |
C2—C3—C4—N2 | 89.18 (16) | C6—C7—C8—N2 | −0.1 (3) |
Symmetry code: (i) −x+1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N2ii | 0.85 (1) | 2.31 (1) | 3.0503 (18) | 146 (1) |
Symmetry code: (ii) −x+1, y−1/2, −z+3/2. |