organic compounds
(E)-1,1-Diphenyl-2-(thiophen-2-ylmethylidene)hydrazine
aFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla 72570, Puebla, Pue., Mexico, and bFacultad de Química, Universidad Nacional Autónoma de México, 04510, México DF, Mexico
*Correspondence e-mail: bmcabreravivas@yahoo.com
The 17H14N2S, consists of two crystallographically independent molecules with similar conformations. The dihedral angles between the phenyl rings are 89.32 (5) and 82.80 (5)° in the two molecules. In the crystal, molecules are linked by C—H⋯π interactions, forming a three-dimensional network.
of the title compound, CCCDC reference: 977136
Related literature
For biological applications of hydrazine derivatives, see: Vogel et al. (2008); Moreira et al. (2012); Vicini et al. (2009); Belkheiri et al. (2010); Shen et al. (2011).
Experimental
Crystal data
|
Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
CCDC reference: 977136
https://doi.org/10.1107/S1600536813033874/is5326sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033874/is5326Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536813033874/is5326Isup3.cml
491 mg (2.6 mmol) phenylhydrazine were dissolved in ethanol and acetic acid (0.5 ml) was slowly added into this solution while stirring, 300 mg (2.6 mmol) of thiophene-2-carbaldehyde, were added drop by drop into the above solution strongly stirring and the resulting mixture was kept at room temperature until it became a beige-coloured solution. After one and a half hours the solution precipitated. The reaction was monitored by TLC, aluminium AlugramSil G/UV254. The mixture was separated with filtration in vacuo system and the precipitate was washed three times with cold methanol. Recrystallization was performed with acetonitrile to obtain amber crystals for X-ray analysis. Yield 90%, amber needle, UV λmax = 345.15 nm. FT IR (film): (cm-1): 3098 ν(C—H), 1586 ν(C=C—S), 1448, 1371 ν(C=N), 1292 ν(C—N), 854 γ(CH-thiophene). 1H NMR (400 MHz, (CD3)2CO: (δ/p.p.m.): 7.45(m,4H,C3'), 7.37 (t,1H,C3), 7.36(s,1H,Ci), 7.19 (m, 6H,C2',C4'), 7.02 (m, 1H,C5), 6.98 (dd, 1H,C4). 13C NMR (400 MHz, (CD3)2CO): (δ/p.p.m.): 141.67, 130.53, 129.89, 127.32, 126.99, 125.61, 124.64, 122.25. MS—EI: m/z = 278.37 M+. C17H14N2S.
H atoms bonded to C atoms were placed in geometrical idealized positions and were refined as riding on their parent atoms, with C—H = 0.95 Å and with Uiso(H) = 1.2Ueq(C).
A great variety of hydrazine derivative compounds have been synthesized, which have been proven to control the growth of cancerous cells (Vogel et al., 2008) or serve as antibiotics (Moreira et al., 2012), inhibitors of HIV (Vicini et al., 2009), anti-inflammatory, and antioxidant agents (Belkheiri et al., 2010). Technologically speaking, hydrazone derivatives have been used to create materials with optical, electrochemical, photophysical and solar cells properties (Shen et al., 2011). In this work we crystallized the (E)-1,1-diphenyl-2-(thiophen-2-ylmethylene)hydrazine.
In the title compound, the ═N double bond. The dihedral angle between the C1A–C6A and C7A–C12A rings is 89.32 (5)° for molecule A close proximity to the orthogonality (90°), while the angle between the C1B–C6B and C7B–C12B rings is 82.80 (5)° for molecule B. The (thiophen-2-ylmethylene)hydrazine group deviates from planarity with an r.m.s. deviation of fitted atoms of 0.0546 [equation: 9.774 (1) x - 2.803 (5) y - 5.122 (8) z = 9.501 (5)] and 0.0331 [equation: 2.970 (5) x - 9.686 (1) y + 5.981 (8) z = 6.359 (5)] for molecules A and B, respectively. The N2A—N1A—C1A [116.17 (13)°] and N2B—N1B—C1B [116.88 (13)°] angles are slightly shorter than the mean (120.28°) value with σ =1.19 in the Cambridge Structural Database, while C13A—N2A—N1A [119.40 (14)°] and C13B—N2B—N1B [118.81 (13)°] angles are slightly larger than the mean (116.14°) reported. In the crystal, C—H···π interactions (Table 1) link the molecule into a three-dimensional network (Fig. 2).
consists of the two (E)-1,1-diphenyl-2-(thiophen-2-ylmethylene)hydrazine non-planar molecules (Fig. 1). Both molecules A (N1A to C17A/S1A) and B (N1B to C17B/S1B) show an E configuration with respect to the CFor biological applications of hydrazine derivatives, see: Vogel et al. (2008); Moreira et al. (2012); Vicini et al. (2009); Belkheiri et al. (2010); Shen et al. (2011).
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 60% probability level and H atoms are shown as circles of arbitrary size. | |
Fig. 2. A packing diagram of the title compound viewed along the a axis. Intermolecular C—H···π interactions are indicated by dotted lines. |
C17H14N2S | Z = 4 |
Mr = 278.36 | F(000) = 584 |
Triclinic, P1 | Dx = 1.284 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8336 (11) Å | Cell parameters from 6444 reflections |
b = 9.8665 (9) Å | θ = 3.6–26.0° |
c = 16.6357 (8) Å | µ = 0.22 mm−1 |
α = 100.290 (6)° | T = 144 K |
β = 101.696 (7)° | Prism, colourless |
γ = 109.129 (9)° | 0.58 × 0.51 × 0.36 mm |
V = 1439.9 (2) Å3 |
Agilent Xcalibur (Atlas, Gemini) diffractometer | 5672 independent reflections |
Graphite monochromator | 4856 reflections with I > 2σ(I) |
Detector resolution: 10.4685 pixels mm-1 | Rint = 0.020 |
ω scans | θmax = 26.1°, θmin = 3.6° |
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012) | h = −12→12 |
Tmin = 0.916, Tmax = 0.939 | k = −10→12 |
10771 measured reflections | l = −20→20 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0382P)2 + 0.4189P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.099 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.23 e Å−3 |
5672 reflections | Δρmin = −0.33 e Å−3 |
361 parameters |
C17H14N2S | γ = 109.129 (9)° |
Mr = 278.36 | V = 1439.9 (2) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.8336 (11) Å | Mo Kα radiation |
b = 9.8665 (9) Å | µ = 0.22 mm−1 |
c = 16.6357 (8) Å | T = 144 K |
α = 100.290 (6)° | 0.58 × 0.51 × 0.36 mm |
β = 101.696 (7)° |
Agilent Xcalibur (Atlas, Gemini) diffractometer | 5672 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012) | 4856 reflections with I > 2σ(I) |
Tmin = 0.916, Tmax = 0.939 | Rint = 0.020 |
10771 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.23 e Å−3 |
5672 reflections | Δρmin = −0.33 e Å−3 |
361 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1A | 0.45980 (5) | 0.49688 (5) | 0.64718 (3) | 0.03525 (13) | |
N1A | 0.22725 (17) | 0.04849 (15) | 0.46812 (8) | 0.0294 (3) | |
N2A | 0.29506 (15) | 0.18305 (15) | 0.52848 (8) | 0.0258 (3) | |
C1A | 0.14928 (18) | 0.05017 (18) | 0.38736 (10) | 0.0230 (3) | |
C2A | 0.17908 (19) | 0.18184 (19) | 0.36238 (11) | 0.0277 (4) | |
H2A | 0.2535 | 0.272 | 0.3995 | 0.033* | |
C3A | 0.0996 (2) | 0.1807 (2) | 0.28310 (11) | 0.0333 (4) | |
H3A | 0.1199 | 0.2709 | 0.2664 | 0.04* | |
C4A | −0.0092 (2) | 0.0502 (2) | 0.22784 (11) | 0.0346 (4) | |
H4A | −0.0628 | 0.0505 | 0.1736 | 0.042* | |
C5A | −0.0385 (2) | −0.0800 (2) | 0.25262 (11) | 0.0328 (4) | |
H5A | −0.113 | −0.1699 | 0.2152 | 0.039* | |
C6A | 0.03982 (19) | −0.08112 (19) | 0.33190 (10) | 0.0284 (4) | |
H6A | 0.0187 | −0.1715 | 0.3483 | 0.034* | |
C7A | 0.21917 (18) | −0.08886 (17) | 0.48812 (10) | 0.0238 (3) | |
C8A | 0.11947 (19) | −0.15270 (19) | 0.53117 (11) | 0.0294 (4) | |
H8A | 0.0551 | −0.106 | 0.5474 | 0.035* | |
C9A | 0.1137 (2) | −0.28481 (19) | 0.55049 (11) | 0.0329 (4) | |
H9A | 0.0454 | −0.3287 | 0.5802 | 0.039* | |
C10A | 0.2069 (2) | −0.35305 (19) | 0.52681 (11) | 0.0328 (4) | |
H10A | 0.2022 | −0.444 | 0.5399 | 0.039* | |
C11A | 0.30686 (19) | −0.28940 (19) | 0.48412 (11) | 0.0320 (4) | |
H11A | 0.3709 | −0.3366 | 0.4679 | 0.038* | |
C12A | 0.31402 (18) | −0.15642 (18) | 0.46491 (10) | 0.0274 (4) | |
H12A | 0.3835 | −0.1119 | 0.436 | 0.033* | |
C13A | 0.35204 (18) | 0.18705 (18) | 0.60598 (10) | 0.0259 (4) | |
H13A | 0.3475 | 0.0974 | 0.6209 | 0.031* | |
C14A | 0.42304 (18) | 0.32729 (18) | 0.67056 (10) | 0.0250 (4) | |
C15A | 0.46818 (19) | 0.34694 (19) | 0.75658 (11) | 0.0309 (4) | |
H15A | 0.4591 | 0.267 | 0.7823 | 0.037* | |
C16A | 0.52983 (18) | 0.49809 (19) | 0.80343 (11) | 0.0309 (4) | |
H16A | 0.5649 | 0.5303 | 0.8638 | 0.037* | |
C17A | 0.5333 (2) | 0.5912 (2) | 0.75320 (12) | 0.0347 (4) | |
H17A | 0.5718 | 0.6965 | 0.7738 | 0.042* | |
S1B | 0.49868 (5) | 0.03271 (5) | −0.12555 (3) | 0.03013 (12) | |
N1B | 0.96060 (14) | 0.28458 (16) | 0.04326 (8) | 0.0260 (3) | |
N2B | 0.82065 (14) | 0.20862 (14) | −0.01346 (8) | 0.0233 (3) | |
C1B | 0.96712 (18) | 0.36467 (17) | 0.12427 (10) | 0.0221 (3) | |
C2B | 0.84018 (19) | 0.33497 (19) | 0.15375 (11) | 0.0271 (4) | |
H2B | 0.7471 | 0.2606 | 0.1192 | 0.032* | |
C3B | 0.8508 (2) | 0.4147 (2) | 0.23387 (11) | 0.0320 (4) | |
H3B | 0.764 | 0.3944 | 0.2537 | 0.038* | |
C4B | 0.9854 (2) | 0.52359 (19) | 0.28560 (11) | 0.0331 (4) | |
H4B | 0.9919 | 0.576 | 0.3409 | 0.04* | |
C5B | 1.1098 (2) | 0.55446 (19) | 0.25521 (11) | 0.0331 (4) | |
H5B | 1.2022 | 0.6302 | 0.2896 | 0.04* | |
C6B | 1.10198 (19) | 0.47654 (18) | 0.17521 (11) | 0.0273 (4) | |
H6B | 1.1884 | 0.4993 | 0.1551 | 0.033* | |
C7B | 1.09374 (17) | 0.29233 (17) | 0.01841 (10) | 0.0217 (3) | |
C8B | 1.15424 (18) | 0.39775 (19) | −0.02261 (10) | 0.0270 (4) | |
H8B | 1.1103 | 0.4682 | −0.0321 | 0.032* | |
C9B | 1.27897 (19) | 0.40038 (19) | −0.04985 (10) | 0.0284 (4) | |
H9B | 1.3209 | 0.4731 | −0.0777 | 0.034* | |
C10B | 1.34251 (18) | 0.29745 (19) | −0.03651 (10) | 0.0274 (4) | |
H10B | 1.4278 | 0.2992 | −0.0555 | 0.033* | |
C11B | 1.28180 (19) | 0.19156 (19) | 0.00450 (11) | 0.0292 (4) | |
H11B | 1.3255 | 0.1209 | 0.0137 | 0.035* | |
C12B | 1.15722 (18) | 0.18903 (18) | 0.03205 (10) | 0.0254 (4) | |
H12B | 1.1155 | 0.1167 | 0.0602 | 0.03* | |
C13B | 0.81062 (18) | 0.14782 (17) | −0.09080 (10) | 0.0235 (3) | |
H13B | 0.8991 | 0.1555 | −0.1075 | 0.028* | |
C14B | 0.66548 (17) | 0.06796 (17) | −0.15229 (10) | 0.0226 (3) | |
C15B | 0.63864 (19) | 0.01036 (19) | −0.23772 (11) | 0.0279 (4) | |
H15B | 0.7159 | 0.0176 | −0.2649 | 0.033* | |
C16B | 0.48434 (19) | −0.06090 (19) | −0.28138 (11) | 0.0304 (4) | |
H16B | 0.447 | −0.1064 | −0.3409 | 0.036* | |
C17B | 0.39578 (19) | −0.05744 (19) | −0.22952 (11) | 0.0313 (4) | |
H17B | 0.2893 | −0.0997 | −0.2482 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0430 (3) | 0.0264 (2) | 0.0326 (3) | 0.0123 (2) | 0.0031 (2) | 0.00904 (19) |
N1A | 0.0417 (9) | 0.0208 (7) | 0.0206 (7) | 0.0096 (6) | 0.0033 (7) | 0.0038 (6) |
N2A | 0.0285 (7) | 0.0226 (7) | 0.0232 (7) | 0.0079 (6) | 0.0062 (6) | 0.0031 (6) |
C1A | 0.0251 (8) | 0.0267 (8) | 0.0198 (8) | 0.0115 (7) | 0.0092 (7) | 0.0055 (7) |
C2A | 0.0304 (9) | 0.0260 (9) | 0.0263 (9) | 0.0095 (7) | 0.0091 (8) | 0.0068 (7) |
C3A | 0.0431 (11) | 0.0354 (10) | 0.0301 (9) | 0.0210 (9) | 0.0133 (9) | 0.0145 (8) |
C4A | 0.0360 (10) | 0.0478 (11) | 0.0251 (9) | 0.0230 (9) | 0.0065 (8) | 0.0104 (8) |
C5A | 0.0287 (9) | 0.0366 (10) | 0.0274 (9) | 0.0113 (8) | 0.0042 (8) | 0.0009 (8) |
C6A | 0.0301 (9) | 0.0266 (9) | 0.0258 (9) | 0.0085 (7) | 0.0078 (8) | 0.0047 (7) |
C7A | 0.0285 (9) | 0.0218 (8) | 0.0183 (8) | 0.0083 (7) | 0.0033 (7) | 0.0044 (6) |
C8A | 0.0260 (9) | 0.0316 (9) | 0.0295 (9) | 0.0102 (7) | 0.0087 (8) | 0.0057 (8) |
C9A | 0.0322 (9) | 0.0311 (10) | 0.0304 (9) | 0.0040 (8) | 0.0081 (8) | 0.0125 (8) |
C10A | 0.0337 (10) | 0.0227 (9) | 0.0324 (10) | 0.0072 (8) | −0.0050 (8) | 0.0074 (8) |
C11A | 0.0297 (9) | 0.0309 (9) | 0.0318 (10) | 0.0154 (8) | 0.0012 (8) | 0.0007 (8) |
C12A | 0.0247 (8) | 0.0282 (9) | 0.0235 (8) | 0.0057 (7) | 0.0063 (7) | 0.0013 (7) |
C13A | 0.0291 (9) | 0.0240 (8) | 0.0249 (9) | 0.0101 (7) | 0.0074 (7) | 0.0071 (7) |
C14A | 0.0228 (8) | 0.0250 (8) | 0.0250 (8) | 0.0082 (7) | 0.0047 (7) | 0.0053 (7) |
C15A | 0.0325 (9) | 0.0296 (9) | 0.0258 (9) | 0.0073 (8) | 0.0052 (8) | 0.0075 (7) |
C16A | 0.0252 (9) | 0.0345 (10) | 0.0238 (9) | 0.0065 (8) | 0.0032 (7) | −0.0014 (8) |
C17A | 0.0293 (9) | 0.0258 (9) | 0.0401 (11) | 0.0083 (8) | 0.0037 (8) | −0.0017 (8) |
S1B | 0.0233 (2) | 0.0401 (3) | 0.0284 (2) | 0.01185 (19) | 0.00921 (19) | 0.0106 (2) |
N1B | 0.0180 (7) | 0.0343 (8) | 0.0204 (7) | 0.0075 (6) | 0.0031 (6) | 0.0014 (6) |
N2B | 0.0205 (7) | 0.0243 (7) | 0.0221 (7) | 0.0069 (6) | 0.0031 (6) | 0.0050 (6) |
C1B | 0.0262 (8) | 0.0232 (8) | 0.0187 (8) | 0.0114 (7) | 0.0047 (7) | 0.0077 (7) |
C2B | 0.0258 (9) | 0.0286 (9) | 0.0258 (9) | 0.0079 (7) | 0.0082 (7) | 0.0082 (7) |
C3B | 0.0393 (10) | 0.0343 (10) | 0.0314 (9) | 0.0176 (8) | 0.0194 (9) | 0.0129 (8) |
C4B | 0.0491 (11) | 0.0275 (9) | 0.0254 (9) | 0.0173 (8) | 0.0138 (9) | 0.0044 (7) |
C5B | 0.0373 (10) | 0.0269 (9) | 0.0268 (9) | 0.0084 (8) | 0.0030 (8) | 0.0015 (7) |
C6B | 0.0268 (9) | 0.0284 (9) | 0.0253 (9) | 0.0097 (7) | 0.0061 (7) | 0.0063 (7) |
C7B | 0.0184 (8) | 0.0244 (8) | 0.0174 (7) | 0.0058 (6) | 0.0022 (6) | 0.0012 (6) |
C8B | 0.0266 (9) | 0.0284 (9) | 0.0267 (9) | 0.0117 (7) | 0.0050 (7) | 0.0097 (7) |
C9B | 0.0290 (9) | 0.0293 (9) | 0.0242 (9) | 0.0064 (7) | 0.0078 (7) | 0.0094 (7) |
C10B | 0.0217 (8) | 0.0328 (9) | 0.0240 (8) | 0.0084 (7) | 0.0078 (7) | 0.0009 (7) |
C11B | 0.0278 (9) | 0.0258 (9) | 0.0329 (9) | 0.0126 (7) | 0.0053 (8) | 0.0039 (7) |
C12B | 0.0262 (9) | 0.0218 (8) | 0.0248 (8) | 0.0062 (7) | 0.0056 (7) | 0.0056 (7) |
C13B | 0.0218 (8) | 0.0253 (8) | 0.0234 (8) | 0.0089 (7) | 0.0060 (7) | 0.0065 (7) |
C14B | 0.0230 (8) | 0.0226 (8) | 0.0232 (8) | 0.0094 (7) | 0.0073 (7) | 0.0060 (7) |
C15B | 0.0250 (9) | 0.0321 (9) | 0.0254 (9) | 0.0111 (7) | 0.0073 (7) | 0.0044 (7) |
C16B | 0.0302 (9) | 0.0284 (9) | 0.0252 (9) | 0.0092 (7) | −0.0012 (8) | 0.0033 (7) |
C17B | 0.0217 (8) | 0.0317 (9) | 0.0356 (10) | 0.0072 (7) | 0.0004 (8) | 0.0113 (8) |
S1A—C17A | 1.7190 (19) | S1B—C17B | 1.7198 (18) |
S1A—C14A | 1.7247 (17) | S1B—C14B | 1.7281 (16) |
N1A—N2A | 1.3739 (19) | N1B—N2B | 1.3751 (18) |
N1A—C1A | 1.411 (2) | N1B—C1B | 1.413 (2) |
N1A—C7A | 1.433 (2) | N1B—C7B | 1.434 (2) |
N2A—C13A | 1.285 (2) | N2B—C13B | 1.288 (2) |
C1A—C2A | 1.392 (2) | C1B—C2B | 1.394 (2) |
C1A—C6A | 1.394 (2) | C1B—C6B | 1.395 (2) |
C2A—C3A | 1.386 (2) | C2B—C3B | 1.386 (2) |
C2A—H2A | 0.95 | C2B—H2B | 0.95 |
C3A—C4A | 1.387 (3) | C3B—C4B | 1.387 (3) |
C3A—H3A | 0.95 | C3B—H3B | 0.95 |
C4A—C5A | 1.378 (3) | C4B—C5B | 1.381 (3) |
C4A—H4A | 0.95 | C4B—H4B | 0.95 |
C5A—C6A | 1.390 (2) | C5B—C6B | 1.386 (2) |
C5A—H5A | 0.95 | C5B—H5B | 0.95 |
C6A—H6A | 0.95 | C6B—H6B | 0.95 |
C7A—C8A | 1.383 (2) | C7B—C8B | 1.384 (2) |
C7A—C12A | 1.387 (2) | C7B—C12B | 1.386 (2) |
C8A—C9A | 1.384 (2) | C8B—C9B | 1.385 (2) |
C8A—H8A | 0.95 | C8B—H8B | 0.95 |
C9A—C10A | 1.379 (3) | C9B—C10B | 1.382 (2) |
C9A—H9A | 0.95 | C9B—H9B | 0.95 |
C10A—C11A | 1.379 (3) | C10B—C11B | 1.387 (2) |
C10A—H10A | 0.95 | C10B—H10B | 0.95 |
C11A—C12A | 1.388 (2) | C11B—C12B | 1.387 (2) |
C11A—H11A | 0.95 | C11B—H11B | 0.95 |
C12A—H12A | 0.95 | C12B—H12B | 0.95 |
C13A—C14A | 1.445 (2) | C13B—C14B | 1.445 (2) |
C13A—H13A | 0.95 | C13B—H13B | 0.95 |
C14A—C15A | 1.367 (2) | C14B—C15B | 1.369 (2) |
C15A—C16A | 1.414 (2) | C15B—C16B | 1.413 (2) |
C15A—H15A | 0.95 | C15B—H15B | 0.95 |
C16A—C17A | 1.345 (3) | C16B—C17B | 1.348 (3) |
C16A—H16A | 0.95 | C16B—H16B | 0.95 |
C17A—H17A | 0.95 | C17B—H17B | 0.95 |
C17A—S1A—C14A | 91.75 (9) | C17B—S1B—C14B | 91.65 (8) |
N2A—N1A—C1A | 116.17 (13) | N2B—N1B—C1B | 116.88 (13) |
N2A—N1A—C7A | 122.29 (13) | N2B—N1B—C7B | 121.16 (12) |
C1A—N1A—C7A | 121.09 (13) | C1B—N1B—C7B | 121.74 (13) |
C13A—N2A—N1A | 119.40 (14) | C13B—N2B—N1B | 118.81 (13) |
C2A—C1A—C6A | 119.30 (15) | C2B—C1B—C6B | 119.38 (15) |
C2A—C1A—N1A | 120.86 (15) | C2B—C1B—N1B | 121.00 (15) |
C6A—C1A—N1A | 119.83 (15) | C6B—C1B—N1B | 119.62 (14) |
C3A—C2A—C1A | 119.70 (16) | C3B—C2B—C1B | 119.53 (16) |
C3A—C2A—H2A | 120.1 | C3B—C2B—H2B | 120.2 |
C1A—C2A—H2A | 120.1 | C1B—C2B—H2B | 120.2 |
C2A—C3A—C4A | 121.05 (17) | C2B—C3B—C4B | 121.33 (16) |
C2A—C3A—H3A | 119.5 | C2B—C3B—H3B | 119.3 |
C4A—C3A—H3A | 119.5 | C4B—C3B—H3B | 119.3 |
C5A—C4A—C3A | 119.19 (16) | C5B—C4B—C3B | 118.76 (16) |
C5A—C4A—H4A | 120.4 | C5B—C4B—H4B | 120.6 |
C3A—C4A—H4A | 120.4 | C3B—C4B—H4B | 120.6 |
C4A—C5A—C6A | 120.59 (17) | C4B—C5B—C6B | 120.98 (17) |
C4A—C5A—H5A | 119.7 | C4B—C5B—H5B | 119.5 |
C6A—C5A—H5A | 119.7 | C6B—C5B—H5B | 119.5 |
C5A—C6A—C1A | 120.16 (16) | C5B—C6B—C1B | 119.99 (16) |
C5A—C6A—H6A | 119.9 | C5B—C6B—H6B | 120 |
C1A—C6A—H6A | 119.9 | C1B—C6B—H6B | 120 |
C8A—C7A—C12A | 120.14 (15) | C8B—C7B—C12B | 120.21 (15) |
C8A—C7A—N1A | 120.52 (15) | C8B—C7B—N1B | 120.15 (14) |
C12A—C7A—N1A | 119.34 (14) | C12B—C7B—N1B | 119.57 (14) |
C7A—C8A—C9A | 119.80 (16) | C7B—C8B—C9B | 119.86 (15) |
C7A—C8A—H8A | 120.1 | C7B—C8B—H8B | 120.1 |
C9A—C8A—H8A | 120.1 | C9B—C8B—H8B | 120.1 |
C10A—C9A—C8A | 120.23 (16) | C10B—C9B—C8B | 120.13 (15) |
C10A—C9A—H9A | 119.9 | C10B—C9B—H9B | 119.9 |
C8A—C9A—H9A | 119.9 | C8B—C9B—H9B | 119.9 |
C11A—C10A—C9A | 120.12 (16) | C9B—C10B—C11B | 120.04 (15) |
C11A—C10A—H10A | 119.9 | C9B—C10B—H10B | 120 |
C9A—C10A—H10A | 119.9 | C11B—C10B—H10B | 120 |
C10A—C11A—C12A | 120.06 (16) | C12B—C11B—C10B | 119.91 (16) |
C10A—C11A—H11A | 120 | C12B—C11B—H11B | 120 |
C12A—C11A—H11A | 120 | C10B—C11B—H11B | 120 |
C7A—C12A—C11A | 119.65 (15) | C7B—C12B—C11B | 119.83 (15) |
C7A—C12A—H12A | 120.2 | C7B—C12B—H12B | 120.1 |
C11A—C12A—H12A | 120.2 | C11B—C12B—H12B | 120.1 |
N2A—C13A—C14A | 120.29 (15) | N2B—C13B—C14B | 120.34 (15) |
N2A—C13A—H13A | 119.9 | N2B—C13B—H13B | 119.8 |
C14A—C13A—H13A | 119.9 | C14B—C13B—H13B | 119.8 |
C15A—C14A—C13A | 126.66 (16) | C15B—C14B—C13B | 126.43 (15) |
C15A—C14A—S1A | 110.41 (13) | C15B—C14B—S1B | 110.52 (12) |
C13A—C14A—S1A | 122.92 (13) | C13B—C14B—S1B | 123.05 (12) |
C14A—C15A—C16A | 113.27 (16) | C14B—C15B—C16B | 113.16 (15) |
C14A—C15A—H15A | 123.4 | C14B—C15B—H15B | 123.4 |
C16A—C15A—H15A | 123.4 | C16B—C15B—H15B | 123.4 |
C17A—C16A—C15A | 112.64 (16) | C17B—C16B—C15B | 112.77 (16) |
C17A—C16A—H16A | 123.7 | C17B—C16B—H16B | 123.6 |
C15A—C16A—H16A | 123.7 | C15B—C16B—H16B | 123.6 |
C16A—C17A—S1A | 111.92 (13) | C16B—C17B—S1B | 111.90 (13) |
C16A—C17A—H17A | 124 | C16B—C17B—H17B | 124.1 |
S1A—C17A—H17A | 124 | S1B—C17B—H17B | 124.1 |
C1A—N1A—N2A—C13A | 171.50 (14) | C1B—N1B—N2B—C13B | 172.48 (14) |
C7A—N1A—N2A—C13A | −0.8 (2) | C7B—N1B—N2B—C13B | −2.2 (2) |
N2A—N1A—C1A—C2A | 19.8 (2) | N2B—N1B—C1B—C2B | 17.7 (2) |
C7A—N1A—C1A—C2A | −167.71 (15) | C7B—N1B—C1B—C2B | −167.66 (14) |
N2A—N1A—C1A—C6A | −159.52 (14) | N2B—N1B—C1B—C6B | −161.46 (14) |
C7A—N1A—C1A—C6A | 12.9 (2) | C7B—N1B—C1B—C6B | 13.2 (2) |
C6A—C1A—C2A—C3A | 0.2 (2) | C6B—C1B—C2B—C3B | −1.4 (2) |
N1A—C1A—C2A—C3A | −179.22 (15) | N1B—C1B—C2B—C3B | 179.43 (15) |
C1A—C2A—C3A—C4A | −0.2 (3) | C1B—C2B—C3B—C4B | −0.1 (3) |
C2A—C3A—C4A—C5A | 0.2 (3) | C2B—C3B—C4B—C5B | 1.5 (3) |
C3A—C4A—C5A—C6A | −0.1 (3) | C3B—C4B—C5B—C6B | −1.3 (3) |
C4A—C5A—C6A—C1A | 0.0 (3) | C4B—C5B—C6B—C1B | −0.3 (3) |
C2A—C1A—C6A—C5A | 0.0 (2) | C2B—C1B—C6B—C5B | 1.6 (2) |
N1A—C1A—C6A—C5A | 179.33 (15) | N1B—C1B—C6B—C5B | −179.22 (15) |
N2A—N1A—C7A—C8A | 75.1 (2) | N2B—N1B—C7B—C8B | 83.36 (19) |
C1A—N1A—C7A—C8A | −96.82 (19) | C1B—N1B—C7B—C8B | −91.07 (19) |
N2A—N1A—C7A—C12A | −103.95 (18) | N2B—N1B—C7B—C12B | −93.54 (18) |
C1A—N1A—C7A—C12A | 84.1 (2) | C1B—N1B—C7B—C12B | 92.03 (19) |
C12A—C7A—C8A—C9A | −0.5 (2) | C12B—C7B—C8B—C9B | −0.2 (2) |
N1A—C7A—C8A—C9A | −179.57 (15) | N1B—C7B—C8B—C9B | −177.12 (14) |
C7A—C8A—C9A—C10A | −0.1 (3) | C7B—C8B—C9B—C10B | 0.3 (2) |
C8A—C9A—C10A—C11A | 0.4 (3) | C8B—C9B—C10B—C11B | −0.3 (3) |
C9A—C10A—C11A—C12A | 0.0 (3) | C9B—C10B—C11B—C12B | 0.0 (3) |
C8A—C7A—C12A—C11A | 0.9 (2) | C8B—C7B—C12B—C11B | 0.0 (2) |
N1A—C7A—C12A—C11A | 179.96 (15) | N1B—C7B—C12B—C11B | 176.93 (14) |
C10A—C11A—C12A—C7A | −0.6 (2) | C10B—C11B—C12B—C7B | 0.1 (2) |
N1A—N2A—C13A—C14A | −179.61 (14) | N1B—N2B—C13B—C14B | −179.59 (13) |
N2A—C13A—C14A—C15A | 169.63 (17) | N2B—C13B—C14B—C15B | 173.46 (16) |
N2A—C13A—C14A—S1A | −9.3 (2) | N2B—C13B—C14B—S1B | −6.5 (2) |
C17A—S1A—C14A—C15A | −0.57 (14) | C17B—S1B—C14B—C15B | −0.43 (13) |
C17A—S1A—C14A—C13A | 178.54 (15) | C17B—S1B—C14B—C13B | 179.51 (14) |
C13A—C14A—C15A—C16A | −178.07 (16) | C13B—C14B—C15B—C16B | −179.54 (15) |
S1A—C14A—C15A—C16A | 1.0 (2) | S1B—C14B—C15B—C16B | 0.40 (19) |
C14A—C15A—C16A—C17A | −1.0 (2) | C14B—C15B—C16B—C17B | −0.1 (2) |
C15A—C16A—C17A—S1A | 0.6 (2) | C15B—C16B—C17B—S1B | −0.2 (2) |
C14A—S1A—C17A—C16A | 0.00 (14) | C14B—S1B—C17B—C16B | 0.35 (14) |
Cg2, Cg3, Cg5 and Cg6 are the centroids of the C1A–C6A, C7A–C12A, C1B–C6B and C7B–C12B phenyl rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3A—H3A···Cg5i | 0.95 | 2.76 | 3.553 (2) | 141 |
C8A—H8A···Cg2ii | 0.95 | 2.97 | 3.740 (2) | 139 |
C15B—H15B···Cg2iii | 0.95 | 2.60 | 3.484 (2) | 156 |
C16A—H16A···Cg6iv | 0.95 | 2.72 | 3.5725 (19) | 150 |
C16B—H16B···Cg3v | 0.95 | 2.80 | 3.659 (2) | 151 |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y, −z+1; (iii) −x+1, −y, −z; (iv) −x+2, −y+1, −z+1; (v) x, y, z−1. |
Cg2, Cg3, Cg5 and Cg6 are the centroids of the C1A–C6A, C7A–C12A, C1B–C6B and C7B–C12B phenyl rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3A—H3A···Cg5i | 0.95 | 2.76 | 3.553 (2) | 141 |
C8A—H8A···Cg2ii | 0.95 | 2.97 | 3.740 (2) | 139 |
C15B—H15B···Cg2iii | 0.95 | 2.60 | 3.484 (2) | 156 |
C16A—H16A···Cg6iv | 0.95 | 2.72 | 3.5725 (19) | 150 |
C16B—H16B···Cg3v | 0.95 | 2.80 | 3.659 (2) | 151 |
Symmetry codes: (i) x−1, y, z; (ii) −x, −y, −z+1; (iii) −x+1, −y, −z; (iv) −x+2, −y+1, −z+1; (v) x, y, z−1. |
Acknowledgements
We are grateful for financial support by project Nos. CAVB-NAT13-G, VIEP, BUAP and MELR-NAT13-G. MFA is indebted to Dr A. L. Maldonado-Hermenegildo for useful comments.
References
Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England. Google Scholar
Belkheiri, N., Bouguerne, B., Bedos-Belval, F., Duran, H., Bernis, C., Salvayre, R., Nègre-Salvayre, A. & Baltas, M. (2010). Eur. J. Med. Chem. 45, 3019–3026. Web of Science CrossRef CAS PubMed Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Moreira, T., Delle, F., Domeneghini, L., Mascarello, A., Stumpf, T. R., Zanetti, C. R., Bardini, D., Célia Regina Monte, C. R., Albino, E. F., Viancelli, A., Totaro, L. A., Yunes, R. A., Nunes, R. J. & Smânia, A. (2012). Bioorg. Med. Chem. Lett. 22, 225–230. PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shen, P., Liu, X., Jiang, Sh., Huang, Y., Yi, L., Zhao, B. & Tan, S. (2011). Org. Electron. 12, 1992–2002. Web of Science CrossRef CAS Google Scholar
Vicini, P., Incerti, M., Colla, P. & Loddo, R. (2009). Eur. J. Med. Chem. 44, 1801–1807. Web of Science CrossRef PubMed CAS Google Scholar
Vogel, S., Kaufmann, D., Pojarová, M., Müller, Ch., Pfaller, T., Kühne, S., Bednarski, P. J. & von Angerer, E. (2008). Bioorg. Med. Chem. 16, 6436–6447. Web of Science CrossRef PubMed CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
A great variety of hydrazine derivative compounds have been synthesized, which have been proven to control the growth of cancerous cells (Vogel et al., 2008) or serve as antibiotics (Moreira et al., 2012), inhibitors of HIV (Vicini et al., 2009), anti-inflammatory, and antioxidant agents (Belkheiri et al., 2010). Technologically speaking, hydrazone derivatives have been used to create materials with optical, electrochemical, photophysical and solar cells properties (Shen et al., 2011). In this work we crystallized the (E)-1,1-diphenyl-2-(thiophen-2-ylmethylene)hydrazine.
In the title compound, the asymmetric unit consists of the two (E)-1,1-diphenyl-2-(thiophen-2-ylmethylene)hydrazine non-planar molecules (Fig. 1). Both molecules A (N1A to C17A/S1A) and B (N1B to C17B/S1B) show an E configuration with respect to the C═N double bond. The dihedral angle between the C1A–C6A and C7A–C12A rings is 89.32 (5)° for molecule A close proximity to the orthogonality (90°), while the angle between the C1B–C6B and C7B–C12B rings is 82.80 (5)° for molecule B. The (thiophen-2-ylmethylene)hydrazine group deviates from planarity with an r.m.s. deviation of fitted atoms of 0.0546 [equation: 9.774 (1) x - 2.803 (5) y - 5.122 (8) z = 9.501 (5)] and 0.0331 [equation: 2.970 (5) x - 9.686 (1) y + 5.981 (8) z = 6.359 (5)] for molecules A and B, respectively. The N2A—N1A—C1A [116.17 (13)°] and N2B—N1B—C1B [116.88 (13)°] angles are slightly shorter than the mean (120.28°) value with σ =1.19 in the Cambridge Structural Database, while C13A—N2A—N1A [119.40 (14)°] and C13B—N2B—N1B [118.81 (13)°] angles are slightly larger than the mean (116.14°) reported. In the crystal, C—H···π interactions (Table 1) link the molecule into a three-dimensional network (Fig. 2).