Related literature
For a related structure, see: Girgis (2006
).
Experimental
Crystal data
C11H16N4S Mr = 236.34 Monoclinic, P 21 /n a = 10.517 (2) Å b = 12.873 (3) Å c = 10.552 (2) Å β = 119.19 (3)° V = 1247.3 (4) Å3 Z = 4 Mo Kα radiation μ = 0.24 mm−1 T = 293 K 0.22 × 0.20 × 0.18 mm
|
Data collection
Bruker SMART CCD diffractometer 11842 measured reflections 2847 independent reflections 2391 reflections with I > 2σ(I) Rint = 0.031
|
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | N4—H4A⋯N2 | 0.86 | 2.22 | 2.613 (2) | 108 | N3—H3A⋯S1i | 0.86 | 2.59 | 3.3890 (16) | 155 | Symmetry code: (i) -x+1, -y, -z. | |
Data collection: SMART (Bruker 1997
); cell refinement: SAINT (Bruker 1997
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: SHELXTL (Sheldrick, 2008
); software used to prepare material for publication: SHELXTL.
Supporting information
A mixture of 4-(dimethylamino)benzaldehyde (0.10 mol), and 4-methylthiosemicarbazide (0.10 mol) was stirred in refluxing ethanol (10 ml) for 4 h to afford the title compound (0.083 mol, yield 83%). Colourless blocks of (I) were obtained by recrystallization from ethanol at room temperature.
H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances = 0.93-0.97 Å; N—H = 0.86Å and with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(Cmethyl).
Structure description
top For a related structure, see: Girgis (2006).
Data collection: SMART (Bruker 1997); cell refinement: SAINT (Bruker 1997); data reduction: SAINT (Bruker 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
1-(4-(Dimethylamino)benzylidene)-4-methylthiosemicarbazide
top Crystal data top C11H16N4S | F(000) = 504 |
Mr = 236.34 | Dx = 1.259 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2391 reflections |
a = 10.517 (2) Å | θ = 3.2–27.5° |
b = 12.873 (3) Å | µ = 0.24 mm−1 |
c = 10.552 (2) Å | T = 293 K |
β = 119.19 (3)° | Block, colorless |
V = 1247.3 (4) Å3 | 0.22 × 0.20 × 0.18 mm |
Z = 4 | |
Data collection top Bruker SMART CCD diffractometer | 2391 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 27.5°, θmin = 3.2° |
phi and ω scans | h = −13→11 |
11842 measured reflections | k = −15→16 |
2847 independent reflections | l = −13→13 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.178 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.1186P)2 + 0.111P] where P = (Fo2 + 2Fc2)/3 |
2847 reflections | (Δ/σ)max < 0.001 |
145 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Crystal data top C11H16N4S | V = 1247.3 (4) Å3 |
Mr = 236.34 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.517 (2) Å | µ = 0.24 mm−1 |
b = 12.873 (3) Å | T = 293 K |
c = 10.552 (2) Å | 0.22 × 0.20 × 0.18 mm |
β = 119.19 (3)° | |
Data collection top Bruker SMART CCD diffractometer | 2391 reflections with I > 2σ(I) |
11842 measured reflections | Rint = 0.031 |
2847 independent reflections | |
Refinement top R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.178 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.43 e Å−3 |
2847 reflections | Δρmin = −0.26 e Å−3 |
145 parameters | |
Special details top Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | 0.60342 (4) | 0.15360 (4) | 0.05021 (6) | 0.0595 (2) | |
N2 | 0.17952 (14) | 0.12707 (11) | −0.13146 (16) | 0.0468 (3) | |
N3 | 0.32723 (14) | 0.10421 (10) | −0.05970 (16) | 0.0491 (4) | |
H3A | 0.3569 | 0.0426 | −0.0272 | 0.059* | |
C6 | −0.06129 (17) | 0.06639 (12) | −0.20701 (17) | 0.0435 (4) | |
N4 | 0.36809 (16) | 0.27166 (11) | −0.09695 (18) | 0.0537 (4) | |
H4A | 0.2749 | 0.2772 | −0.1463 | 0.064* | |
C3 | −0.36590 (17) | 0.09210 (14) | −0.32393 (17) | 0.0481 (4) | |
C7 | −0.13111 (19) | 0.15789 (12) | −0.2769 (2) | 0.0495 (4) | |
H7A | −0.0763 | 0.2116 | −0.2848 | 0.059* | |
C10 | 0.42361 (17) | 0.17963 (13) | −0.04141 (17) | 0.0433 (4) | |
C9 | 0.09536 (17) | 0.05248 (12) | −0.13907 (18) | 0.0448 (4) | |
H9A | 0.1355 | −0.0119 | −0.1002 | 0.054* | |
C5 | −0.14729 (19) | −0.01233 (13) | −0.1990 (2) | 0.0501 (4) | |
H5A | −0.1036 | −0.0746 | −0.1543 | 0.060* | |
C8 | −0.27852 (19) | 0.17078 (14) | −0.3344 (2) | 0.0537 (4) | |
H8A | −0.3215 | 0.2327 | −0.3812 | 0.064* | |
C4 | −0.29596 (19) | −0.00089 (14) | −0.2553 (2) | 0.0529 (4) | |
H4B | −0.3502 | −0.0552 | −0.2478 | 0.063* | |
N1 | −0.51338 (16) | 0.10490 (14) | −0.38125 (18) | 0.0634 (4) | |
C2 | −0.5998 (2) | 0.0282 (2) | −0.3574 (3) | 0.0758 (6) | |
H2B | −0.5423 | −0.0329 | −0.3152 | 0.114* | |
H2C | −0.6834 | 0.0107 | −0.4484 | 0.114* | |
H2D | −0.6313 | 0.0560 | −0.2929 | 0.114* | |
C11 | 0.4544 (2) | 0.36333 (16) | −0.0797 (3) | 0.0730 (6) | |
H12A | 0.3912 | 0.4207 | −0.1293 | 0.109* | |
H12B | 0.5174 | 0.3507 | −0.1201 | 0.109* | |
H12C | 0.5120 | 0.3795 | 0.0216 | 0.109* | |
C1 | −0.5822 (2) | 0.2016 (2) | −0.4442 (3) | 0.0929 (8) | |
H1A | −0.5142 | 0.2460 | −0.4541 | 0.139* | |
H1B | −0.6138 | 0.2345 | −0.3828 | 0.139* | |
H1C | −0.6647 | 0.1893 | −0.5381 | 0.139* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0340 (3) | 0.0526 (3) | 0.0744 (4) | −0.00233 (15) | 0.0127 (2) | −0.00072 (19) |
N2 | 0.0336 (7) | 0.0484 (7) | 0.0547 (8) | 0.0008 (5) | 0.0187 (6) | 0.0001 (6) |
N3 | 0.0335 (6) | 0.0439 (7) | 0.0637 (8) | 0.0010 (5) | 0.0188 (6) | 0.0032 (6) |
C6 | 0.0375 (8) | 0.0465 (8) | 0.0464 (8) | −0.0018 (6) | 0.0205 (6) | −0.0026 (6) |
N4 | 0.0395 (7) | 0.0477 (8) | 0.0626 (9) | −0.0017 (5) | 0.0160 (6) | 0.0071 (6) |
C3 | 0.0382 (8) | 0.0593 (10) | 0.0458 (8) | −0.0015 (6) | 0.0197 (6) | −0.0050 (7) |
C7 | 0.0438 (9) | 0.0455 (9) | 0.0594 (10) | −0.0032 (6) | 0.0253 (8) | 0.0021 (7) |
C10 | 0.0382 (7) | 0.0455 (8) | 0.0436 (8) | −0.0027 (6) | 0.0180 (6) | −0.0032 (6) |
C9 | 0.0391 (8) | 0.0437 (8) | 0.0504 (8) | −0.0006 (6) | 0.0210 (6) | −0.0012 (6) |
C5 | 0.0446 (9) | 0.0455 (8) | 0.0572 (10) | −0.0021 (6) | 0.0226 (8) | 0.0055 (7) |
C8 | 0.0447 (9) | 0.0481 (9) | 0.0653 (11) | 0.0052 (7) | 0.0245 (8) | 0.0049 (7) |
C4 | 0.0433 (9) | 0.0567 (9) | 0.0582 (10) | −0.0095 (7) | 0.0245 (8) | 0.0025 (7) |
N1 | 0.0370 (8) | 0.0805 (11) | 0.0677 (10) | −0.0010 (7) | 0.0218 (7) | 0.0000 (8) |
C2 | 0.0468 (10) | 0.1131 (18) | 0.0689 (12) | −0.0167 (11) | 0.0293 (9) | −0.0044 (12) |
C11 | 0.0597 (12) | 0.0529 (10) | 0.0951 (16) | −0.0073 (9) | 0.0289 (11) | 0.0121 (10) |
C1 | 0.0477 (11) | 0.0861 (17) | 0.128 (2) | 0.0166 (11) | 0.0301 (13) | −0.0016 (16) |
Geometric parameters (Å, º) top S1—C10 | 1.6852 (17) | C9—H9A | 0.9300 |
N2—C9 | 1.282 (2) | C5—C4 | 1.383 (3) |
N2—N3 | 1.3877 (19) | C5—H5A | 0.9300 |
N3—C10 | 1.348 (2) | C8—H8A | 0.9300 |
N3—H3A | 0.8600 | C4—H4B | 0.9300 |
C6—C5 | 1.388 (2) | N1—C1 | 1.431 (3) |
C6—C7 | 1.394 (2) | N1—C2 | 1.444 (3) |
C6—C9 | 1.452 (2) | C2—H2B | 0.9600 |
N4—C10 | 1.325 (2) | C2—H2C | 0.9600 |
N4—C11 | 1.445 (2) | C2—H2D | 0.9600 |
N4—H4A | 0.8600 | C11—H12A | 0.9600 |
C3—N1 | 1.372 (2) | C11—H12B | 0.9600 |
C3—C4 | 1.407 (2) | C11—H12C | 0.9600 |
C3—C8 | 1.408 (2) | C1—H1A | 0.9600 |
C7—C8 | 1.372 (2) | C1—H1B | 0.9600 |
C7—H7A | 0.9300 | C1—H1C | 0.9600 |
| | | |
C9—N2—N3 | 115.50 (14) | C7—C8—H8A | 119.4 |
C10—N3—N2 | 119.27 (14) | C3—C8—H8A | 119.4 |
C10—N3—H3A | 120.4 | C5—C4—C3 | 120.64 (15) |
N2—N3—H3A | 120.4 | C5—C4—H4B | 119.7 |
C5—C6—C7 | 117.29 (14) | C3—C4—H4B | 119.7 |
C5—C6—C9 | 119.74 (14) | C3—N1—C1 | 121.07 (17) |
C7—C6—C9 | 122.92 (14) | C3—N1—C2 | 120.89 (18) |
C10—N4—C11 | 124.08 (16) | C1—N1—C2 | 117.18 (18) |
C10—N4—H4A | 118.0 | N1—C2—H2B | 109.5 |
C11—N4—H4A | 118.0 | N1—C2—H2C | 109.5 |
N1—C3—C4 | 121.59 (16) | H2B—C2—H2C | 109.5 |
N1—C3—C8 | 121.31 (16) | N1—C2—H2D | 109.5 |
C4—C3—C8 | 117.07 (14) | H2B—C2—H2D | 109.5 |
C8—C7—C6 | 121.76 (15) | H2C—C2—H2D | 109.5 |
C8—C7—H7A | 119.1 | N4—C11—H12A | 109.5 |
C6—C7—H7A | 119.1 | N4—C11—H12B | 109.5 |
N4—C10—N3 | 116.27 (14) | H12A—C11—H12B | 109.5 |
N4—C10—S1 | 124.11 (13) | N4—C11—H12C | 109.5 |
N3—C10—S1 | 119.61 (13) | H12A—C11—H12C | 109.5 |
N2—C9—C6 | 121.42 (15) | H12B—C11—H12C | 109.5 |
N2—C9—H9A | 119.3 | N1—C1—H1A | 109.5 |
C6—C9—H9A | 119.3 | N1—C1—H1B | 109.5 |
C4—C5—C6 | 121.98 (15) | H1A—C1—H1B | 109.5 |
C4—C5—H5A | 119.0 | N1—C1—H1C | 109.5 |
C6—C5—H5A | 119.0 | H1A—C1—H1C | 109.5 |
C7—C8—C3 | 121.23 (16) | H1B—C1—H1C | 109.5 |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4A···N2 | 0.86 | 2.22 | 2.613 (2) | 108 |
N3—H3A···S1i | 0.86 | 2.59 | 3.3890 (16) | 155 |
Symmetry code: (i) −x+1, −y, −z. |
Experimental details
Crystal data |
Chemical formula | C11H16N4S |
Mr | 236.34 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 10.517 (2), 12.873 (3), 10.552 (2) |
β (°) | 119.19 (3) |
V (Å3) | 1247.3 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.22 × 0.20 × 0.18 |
|
Data collection |
Diffractometer | Bruker SMART CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11842, 2847, 2391 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.178, 1.12 |
No. of reflections | 2847 |
No. of parameters | 145 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.26 |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4A···N2 | 0.86 | 2.22 | 2.613 (2) | 108 |
N3—H3A···S1i | 0.86 | 2.59 | 3.3890 (16) | 155 |
Symmetry code: (i) −x+1, −y, −z. |
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