supplementary materials
N'-(4-Methylbenzylidene)thiophene-2-carbohydrazide
In the title compound, C13H12N2OS, the dihedral angle between the aromatic rings is 14.84 (17)°. In the crystal, inversion dimers linked by pairs of N-H
O hydrogen bonds generate R22(8) loops.
A mixture of thiophene-2-carbohydrazide (0.10 mol) and 4-methylbenzaldehyde
(0.10 mol) was stirred in refluxing ethanol (10 ml) for 4 h to afford the
title compound (0.079 mol, yield 79%). 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).
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).
N'-(4-Methylbenzylidene)thiophene-2-carbohydrazide
top
Crystal data top
| C13H12N2OS | F(000) = 512 |
| Mr = 244.31 | Dx = 1.340 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1759 reflections |
| a = 14.920 (3) Å | θ = 27.5–3.4° |
| b = 5.3976 (11) Å | µ = 0.25 mm−1 |
| c = 15.636 (3) Å | T = 293 K |
| β = 105.87 (3)° | Block, colorless |
| V = 1211.2 (4) Å3 | 0.22 × 0.20 × 0.18 mm |
| Z = 4 | |
Data collection top
Bruker SMART CCD
diffractometer | 1759 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.051 |
| graphite | θmax = 27.5°, θmin = 3.4° |
| phi and ω scans | h = −19→19 |
| 10416 measured reflections | k = −6→6 |
| 2697 independent reflections | l = −20→20 |
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)] = 0.080 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.275 | H-atom parameters constrained |
| S = 1.08 | w = 1/[σ2(Fo2) + (0.1685P)2 + 0.1567P]
where P = (Fo2 + 2Fc2)/3 |
| 2697 reflections | (Δ/σ)max < 0.001 |
| 154 parameters | Δρmax = 0.73 e Å−3 |
| 0 restraints | Δρmin = −0.47 e Å−3 |
Crystal data top
| C13H12N2OS | V = 1211.2 (4) Å3 |
| Mr = 244.31 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 14.920 (3) Å | µ = 0.25 mm−1 |
| b = 5.3976 (11) Å | T = 293 K |
| c = 15.636 (3) Å | 0.22 × 0.20 × 0.18 mm |
| β = 105.87 (3)° | |
Data collection top
Bruker SMART CCD
diffractometer | 1759 reflections with I > 2σ(I) |
| 10416 measured reflections | Rint = 0.051 |
| 2697 independent reflections | θmax = 27.5° |
Refinement top
| R[F2 > 2σ(F2)] = 0.080 | H-atom parameters constrained |
| wR(F2) = 0.275 | Δρmax = 0.73 e Å−3 |
| S = 1.08 | Δρmin = −0.47 e Å−3 |
| 2697 reflections | Absolute structure: ? |
| 154 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | 0.20737 (7) | 0.6743 (2) | 0.48624 (6) | 0.0649 (4) | |
| N1 | 0.17714 (18) | 0.2992 (5) | 0.59639 (17) | 0.0481 (7) | |
| N2 | 0.09655 (17) | 0.2160 (6) | 0.53950 (16) | 0.0507 (7) | |
| H2A | 0.0658 | 0.1007 | 0.5569 | 0.061* | |
| O1 | −0.00815 (15) | 0.2169 (5) | 0.40660 (15) | 0.0576 (7) | |
| C9 | 0.0635 (2) | 0.3089 (6) | 0.4567 (2) | 0.0461 (7) | |
| C8 | 0.2059 (2) | 0.1867 (6) | 0.6707 (2) | 0.0506 (8) | |
| H8A | 0.1713 | 0.0564 | 0.6841 | 0.061* | |
| C5 | 0.2924 (2) | 0.2600 (6) | 0.7348 (2) | 0.0476 (7) | |
| C10 | 0.11121 (19) | 0.5146 (6) | 0.42646 (19) | 0.0460 (7) | |
| C2 | 0.4649 (2) | 0.3822 (8) | 0.8565 (2) | 0.0573 (9) | |
| C12 | 0.1361 (2) | 0.8109 (7) | 0.3262 (2) | 0.0607 (10) | |
| H12A | 0.1276 | 0.9021 | 0.2741 | 0.073* | |
| C7 | 0.4251 (2) | 0.5308 (8) | 0.7826 (2) | 0.0636 (10) | |
| H7A | 0.4562 | 0.6732 | 0.7732 | 0.076* | |
| C11 | 0.0757 (2) | 0.6016 (6) | 0.3332 (2) | 0.0506 (8) | |
| H11A | 0.0261 | 0.5375 | 0.2889 | 0.061* | |
| C3 | 0.4150 (3) | 0.1770 (7) | 0.8695 (2) | 0.0665 (10) | |
| H3A | 0.4388 | 0.0766 | 0.9188 | 0.080* | |
| C6 | 0.3420 (3) | 0.4727 (8) | 0.7240 (2) | 0.0598 (9) | |
| H6A | 0.3176 | 0.5765 | 0.6758 | 0.072* | |
| C4 | 0.3296 (3) | 0.1174 (8) | 0.8101 (2) | 0.0631 (10) | |
| H4A | 0.2969 | −0.0203 | 0.8211 | 0.076* | |
| C13 | 0.2054 (2) | 0.8631 (7) | 0.4008 (2) | 0.0582 (9) | |
| H13A | 0.2477 | 0.9916 | 0.4041 | 0.070* | |
| C1 | 0.5603 (3) | 0.4412 (11) | 0.9168 (2) | 0.0842 (14) | |
| H1B | 0.5764 | 0.3217 | 0.9640 | 0.126* | |
| H1C | 0.5598 | 0.6038 | 0.9415 | 0.126* | |
| H1D | 0.6054 | 0.4355 | 0.8833 | 0.126* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| S1 | 0.0703 (7) | 0.0624 (8) | 0.0608 (6) | −0.0180 (4) | 0.0157 (5) | −0.0037 (4) |
| N1 | 0.0482 (14) | 0.0436 (16) | 0.0523 (14) | −0.0058 (11) | 0.0134 (11) | −0.0062 (12) |
| N2 | 0.0476 (14) | 0.0518 (18) | 0.0515 (15) | −0.0119 (12) | 0.0119 (11) | −0.0025 (12) |
| O1 | 0.0464 (12) | 0.0575 (16) | 0.0636 (14) | −0.0100 (10) | 0.0059 (10) | −0.0006 (12) |
| C9 | 0.0418 (15) | 0.0428 (19) | 0.0553 (18) | −0.0020 (12) | 0.0160 (13) | −0.0049 (13) |
| C8 | 0.0563 (18) | 0.049 (2) | 0.0486 (17) | −0.0078 (14) | 0.0182 (13) | −0.0002 (14) |
| C5 | 0.0579 (18) | 0.0424 (19) | 0.0443 (15) | −0.0017 (14) | 0.0170 (13) | −0.0032 (13) |
| C10 | 0.0402 (15) | 0.0450 (19) | 0.0521 (16) | 0.0006 (12) | 0.0114 (12) | −0.0028 (13) |
| C2 | 0.0542 (18) | 0.071 (3) | 0.0485 (17) | 0.0056 (16) | 0.0169 (14) | −0.0091 (16) |
| C12 | 0.0487 (18) | 0.067 (3) | 0.067 (2) | 0.0068 (15) | 0.0157 (15) | 0.0172 (18) |
| C7 | 0.063 (2) | 0.070 (3) | 0.0566 (19) | −0.0181 (18) | 0.0147 (15) | −0.0001 (18) |
| C11 | 0.0444 (16) | 0.048 (2) | 0.0649 (19) | 0.0041 (13) | 0.0249 (14) | 0.0159 (15) |
| C3 | 0.077 (2) | 0.063 (3) | 0.052 (2) | 0.0041 (19) | 0.0038 (16) | 0.0088 (17) |
| C6 | 0.069 (2) | 0.055 (2) | 0.0504 (17) | −0.0126 (17) | 0.0085 (15) | 0.0067 (16) |
| C4 | 0.078 (2) | 0.053 (2) | 0.057 (2) | −0.0079 (18) | 0.0159 (17) | 0.0089 (16) |
| C13 | 0.062 (2) | 0.046 (2) | 0.065 (2) | −0.0056 (15) | 0.0150 (16) | 0.0037 (16) |
| C1 | 0.058 (2) | 0.131 (5) | 0.059 (2) | 0.001 (2) | 0.0076 (17) | −0.013 (3) |
Geometric parameters (Å, °) top
| S1—C13 | 1.673 (3) | C2—C1 | 1.511 (5) |
| S1—C10 | 1.715 (3) | C12—C13 | 1.360 (5) |
| N1—C8 | 1.277 (4) | C12—C11 | 1.468 (5) |
| N1—N2 | 1.362 (3) | C12—H12A | 0.9300 |
| N2—C9 | 1.350 (4) | C7—C6 | 1.362 (5) |
| N2—H2A | 0.8600 | C7—H7A | 0.9300 |
| O1—C9 | 1.242 (4) | C11—H11A | 0.9300 |
| C9—C10 | 1.465 (4) | C3—C4 | 1.394 (5) |
| C8—C5 | 1.455 (4) | C3—H3A | 0.9300 |
| C8—H8A | 0.9300 | C6—H6A | 0.9300 |
| C5—C4 | 1.389 (5) | C4—H4A | 0.9300 |
| C5—C6 | 1.400 (5) | C13—H13A | 0.9300 |
| C10—C11 | 1.486 (4) | C1—H1B | 0.9600 |
| C2—C3 | 1.380 (5) | C1—H1C | 0.9600 |
| C2—C7 | 1.399 (5) | C1—H1D | 0.9600 |
| | | |
| C13—S1—C10 | 92.39 (16) | C6—C7—H7A | 119.1 |
| C8—N1—N2 | 117.1 (3) | C2—C7—H7A | 119.1 |
| C9—N2—N1 | 122.0 (3) | C12—C11—C10 | 104.7 (3) |
| C9—N2—H2A | 119.0 | C12—C11—H11A | 127.6 |
| N1—N2—H2A | 119.0 | C10—C11—H11A | 127.6 |
| O1—C9—N2 | 118.8 (3) | C2—C3—C4 | 121.3 (3) |
| O1—C9—C10 | 120.7 (3) | C2—C3—H3A | 119.4 |
| N2—C9—C10 | 120.5 (3) | C4—C3—H3A | 119.4 |
| N1—C8—C5 | 120.8 (3) | C7—C6—C5 | 121.5 (3) |
| N1—C8—H8A | 119.6 | C7—C6—H6A | 119.3 |
| C5—C8—H8A | 119.6 | C5—C6—H6A | 119.3 |
| C4—C5—C6 | 117.0 (3) | C5—C4—C3 | 121.2 (4) |
| C4—C5—C8 | 120.4 (3) | C5—C4—H4A | 119.4 |
| C6—C5—C8 | 122.6 (3) | C3—C4—H4A | 119.4 |
| C9—C10—C11 | 118.8 (3) | C12—C13—S1 | 113.7 (3) |
| C9—C10—S1 | 127.8 (2) | C12—C13—H13A | 123.1 |
| C11—C10—S1 | 113.4 (2) | S1—C13—H13A | 123.1 |
| C3—C2—C7 | 117.2 (3) | C2—C1—H1B | 109.5 |
| C3—C2—C1 | 122.1 (4) | C2—C1—H1C | 109.5 |
| C7—C2—C1 | 120.6 (4) | H1B—C1—H1C | 109.5 |
| C13—C12—C11 | 115.7 (3) | C2—C1—H1D | 109.5 |
| C13—C12—H12A | 122.1 | H1B—C1—H1D | 109.5 |
| C11—C12—H12A | 122.1 | H1C—C1—H1D | 109.5 |
| C6—C7—C2 | 121.8 (4) | | |
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2A···O1i | 0.86 | 2.07 | 2.919 (4) | 170 |
| Symmetry codes: (i) −x, −y, −z+1. |
Table 1
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2A···O1i | 0.86 | 2.07 | 2.919 (4) | 170 |
| Symmetry codes: (i) −x, −y, −z+1. |
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Li, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66. Submitted. [HB5446]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
![[Figure 1]](./hb5447fig1thm.gif)
