supplementary materials


is5326 scheme

Acta Cryst. (2014). E70, o80    [ doi:10.1107/S1600536813033874 ]

(E)-1,1-Diphenyl-2-(thio­phen-2-yl­methyl­idene)hydrazine

B. M. Cabrera-Vivas, M. Flores-Alamo, R. Meléndrez-Luévano, L. Meléndez-Balbuena and J. C. Ramirez

Abstract top

The asymmetric unit of the title compound, C17H14N2S, 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...[pi] inter­actions, forming a three-dimensional network.

Comment top

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 CN 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).

Related literature top

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 top

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.

Refinement top

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).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: 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).

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. A packing diagram of the title compound viewed along the a axis. Intermolecular C—H···π interactions are indicated by dotted lines.
(E)-1,1-Diphenyl-2-(thiophen-2-ylmethylidene)hydrazine top
Crystal data top
C17H14N2SZ = 4
Mr = 278.36F(000) = 584
Triclinic, P1Dx = 1.284 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8336 (11) ÅCell parameters from 6444 reflections
b = 9.8665 (9) Åθ = 3.6–26.0°
c = 16.6357 (8) ŵ = 0.22 mm1
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
Data collection top
Agilent Xcalibur (Atlas, Gemini)
diffractometer
5672 independent reflections
Graphite monochromator4856 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1Rint = 0.020
ω scansθmax = 26.1°, θmin = 3.6°
Absorption correction: multi-scan
(CrysAlis RED; Agilent, 2012)
h = 1212
Tmin = 0.916, Tmax = 0.939k = 1012
10771 measured reflectionsl = 2020
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-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 = 1.07Δρmax = 0.23 e Å3
5672 reflectionsΔρmin = 0.33 e Å3
361 parameters
Crystal data top
C17H14N2Sγ = 109.129 (9)°
Mr = 278.36V = 1439.9 (2) Å3
Triclinic, P1Z = 4
a = 9.8336 (11) ÅMo Kα radiation
b = 9.8665 (9) ŵ = 0.22 mm1
c = 16.6357 (8) ÅT = 144 K
α = 100.290 (6)°0.58 × 0.51 × 0.36 mm
β = 101.696 (7)°
Data collection top
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 = 0.939Rint = 0.020
10771 measured reflectionsθmax = 26.1°
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.099Δρmax = 0.23 e Å3
S = 1.07Δρmin = 0.33 e Å3
5672 reflectionsAbsolute structure: ?
361 parametersAbsolute structure parameter: ?
0 restraintsRogers parameter: ?
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.45980 (5)0.49688 (5)0.64718 (3)0.03525 (13)
N1A0.22725 (17)0.04849 (15)0.46812 (8)0.0294 (3)
N2A0.29506 (15)0.18305 (15)0.52848 (8)0.0258 (3)
C1A0.14928 (18)0.05017 (18)0.38736 (10)0.0230 (3)
C2A0.17908 (19)0.18184 (19)0.36238 (11)0.0277 (4)
H2A0.25350.2720.39950.033*
C3A0.0996 (2)0.1807 (2)0.28310 (11)0.0333 (4)
H3A0.11990.27090.26640.04*
C4A0.0092 (2)0.0502 (2)0.22784 (11)0.0346 (4)
H4A0.06280.05050.17360.042*
C5A0.0385 (2)0.0800 (2)0.25262 (11)0.0328 (4)
H5A0.1130.16990.21520.039*
C6A0.03982 (19)0.08112 (19)0.33190 (10)0.0284 (4)
H6A0.01870.17150.34830.034*
C7A0.21917 (18)0.08886 (17)0.48812 (10)0.0238 (3)
C8A0.11947 (19)0.15270 (19)0.53117 (11)0.0294 (4)
H8A0.05510.1060.54740.035*
C9A0.1137 (2)0.28481 (19)0.55049 (11)0.0329 (4)
H9A0.04540.32870.58020.039*
C10A0.2069 (2)0.35305 (19)0.52681 (11)0.0328 (4)
H10A0.20220.4440.53990.039*
C11A0.30686 (19)0.28940 (19)0.48412 (11)0.0320 (4)
H11A0.37090.33660.46790.038*
C12A0.31402 (18)0.15642 (18)0.46491 (10)0.0274 (4)
H12A0.38350.11190.4360.033*
C13A0.35204 (18)0.18705 (18)0.60598 (10)0.0259 (4)
H13A0.34750.09740.62090.031*
C14A0.42304 (18)0.32729 (18)0.67056 (10)0.0250 (4)
C15A0.46818 (19)0.34694 (19)0.75658 (11)0.0309 (4)
H15A0.45910.2670.78230.037*
C16A0.52983 (18)0.49809 (19)0.80343 (11)0.0309 (4)
H16A0.56490.53030.86380.037*
C17A0.5333 (2)0.5912 (2)0.75320 (12)0.0347 (4)
H17A0.57180.69650.77380.042*
S1B0.49868 (5)0.03271 (5)0.12555 (3)0.03013 (12)
N1B0.96060 (14)0.28458 (16)0.04326 (8)0.0260 (3)
N2B0.82065 (14)0.20862 (14)0.01346 (8)0.0233 (3)
C1B0.96712 (18)0.36467 (17)0.12427 (10)0.0221 (3)
C2B0.84018 (19)0.33497 (19)0.15375 (11)0.0271 (4)
H2B0.74710.26060.11920.032*
C3B0.8508 (2)0.4147 (2)0.23387 (11)0.0320 (4)
H3B0.7640.39440.25370.038*
C4B0.9854 (2)0.52359 (19)0.28560 (11)0.0331 (4)
H4B0.99190.5760.34090.04*
C5B1.1098 (2)0.55446 (19)0.25521 (11)0.0331 (4)
H5B1.20220.63020.28960.04*
C6B1.10198 (19)0.47654 (18)0.17521 (11)0.0273 (4)
H6B1.18840.49930.15510.033*
C7B1.09374 (17)0.29233 (17)0.01841 (10)0.0217 (3)
C8B1.15424 (18)0.39775 (19)0.02261 (10)0.0270 (4)
H8B1.11030.46820.03210.032*
C9B1.27897 (19)0.40038 (19)0.04985 (10)0.0284 (4)
H9B1.32090.47310.07770.034*
C10B1.34251 (18)0.29745 (19)0.03651 (10)0.0274 (4)
H10B1.42780.29920.05550.033*
C11B1.28180 (19)0.19156 (19)0.00450 (11)0.0292 (4)
H11B1.32550.12090.01370.035*
C12B1.15722 (18)0.18903 (18)0.03205 (10)0.0254 (4)
H12B1.11550.11670.06020.03*
C13B0.81062 (18)0.14782 (17)0.09080 (10)0.0235 (3)
H13B0.89910.15550.10750.028*
C14B0.66548 (17)0.06796 (17)0.15229 (10)0.0226 (3)
C15B0.63864 (19)0.01036 (19)0.23772 (11)0.0279 (4)
H15B0.71590.01760.26490.033*
C16B0.48434 (19)0.06090 (19)0.28138 (11)0.0304 (4)
H16B0.4470.10640.34090.036*
C17B0.39578 (19)0.05744 (19)0.22952 (11)0.0313 (4)
H17B0.28930.09970.24820.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0430 (3)0.0264 (2)0.0326 (3)0.0123 (2)0.0031 (2)0.00904 (19)
N1A0.0417 (9)0.0208 (7)0.0206 (7)0.0096 (6)0.0033 (7)0.0038 (6)
N2A0.0285 (7)0.0226 (7)0.0232 (7)0.0079 (6)0.0062 (6)0.0031 (6)
C1A0.0251 (8)0.0267 (8)0.0198 (8)0.0115 (7)0.0092 (7)0.0055 (7)
C2A0.0304 (9)0.0260 (9)0.0263 (9)0.0095 (7)0.0091 (8)0.0068 (7)
C3A0.0431 (11)0.0354 (10)0.0301 (9)0.0210 (9)0.0133 (9)0.0145 (8)
C4A0.0360 (10)0.0478 (11)0.0251 (9)0.0230 (9)0.0065 (8)0.0104 (8)
C5A0.0287 (9)0.0366 (10)0.0274 (9)0.0113 (8)0.0042 (8)0.0009 (8)
C6A0.0301 (9)0.0266 (9)0.0258 (9)0.0085 (7)0.0078 (8)0.0047 (7)
C7A0.0285 (9)0.0218 (8)0.0183 (8)0.0083 (7)0.0033 (7)0.0044 (6)
C8A0.0260 (9)0.0316 (9)0.0295 (9)0.0102 (7)0.0087 (8)0.0057 (8)
C9A0.0322 (9)0.0311 (10)0.0304 (9)0.0040 (8)0.0081 (8)0.0125 (8)
C10A0.0337 (10)0.0227 (9)0.0324 (10)0.0072 (8)0.0050 (8)0.0074 (8)
C11A0.0297 (9)0.0309 (9)0.0318 (10)0.0154 (8)0.0012 (8)0.0007 (8)
C12A0.0247 (8)0.0282 (9)0.0235 (8)0.0057 (7)0.0063 (7)0.0013 (7)
C13A0.0291 (9)0.0240 (8)0.0249 (9)0.0101 (7)0.0074 (7)0.0071 (7)
C14A0.0228 (8)0.0250 (8)0.0250 (8)0.0082 (7)0.0047 (7)0.0053 (7)
C15A0.0325 (9)0.0296 (9)0.0258 (9)0.0073 (8)0.0052 (8)0.0075 (7)
C16A0.0252 (9)0.0345 (10)0.0238 (9)0.0065 (8)0.0032 (7)0.0014 (8)
C17A0.0293 (9)0.0258 (9)0.0401 (11)0.0083 (8)0.0037 (8)0.0017 (8)
S1B0.0233 (2)0.0401 (3)0.0284 (2)0.01185 (19)0.00921 (19)0.0106 (2)
N1B0.0180 (7)0.0343 (8)0.0204 (7)0.0075 (6)0.0031 (6)0.0014 (6)
N2B0.0205 (7)0.0243 (7)0.0221 (7)0.0069 (6)0.0031 (6)0.0050 (6)
C1B0.0262 (8)0.0232 (8)0.0187 (8)0.0114 (7)0.0047 (7)0.0077 (7)
C2B0.0258 (9)0.0286 (9)0.0258 (9)0.0079 (7)0.0082 (7)0.0082 (7)
C3B0.0393 (10)0.0343 (10)0.0314 (9)0.0176 (8)0.0194 (9)0.0129 (8)
C4B0.0491 (11)0.0275 (9)0.0254 (9)0.0173 (8)0.0138 (9)0.0044 (7)
C5B0.0373 (10)0.0269 (9)0.0268 (9)0.0084 (8)0.0030 (8)0.0015 (7)
C6B0.0268 (9)0.0284 (9)0.0253 (9)0.0097 (7)0.0061 (7)0.0063 (7)
C7B0.0184 (8)0.0244 (8)0.0174 (7)0.0058 (6)0.0022 (6)0.0012 (6)
C8B0.0266 (9)0.0284 (9)0.0267 (9)0.0117 (7)0.0050 (7)0.0097 (7)
C9B0.0290 (9)0.0293 (9)0.0242 (9)0.0064 (7)0.0078 (7)0.0094 (7)
C10B0.0217 (8)0.0328 (9)0.0240 (8)0.0084 (7)0.0078 (7)0.0009 (7)
C11B0.0278 (9)0.0258 (9)0.0329 (9)0.0126 (7)0.0053 (8)0.0039 (7)
C12B0.0262 (9)0.0218 (8)0.0248 (8)0.0062 (7)0.0056 (7)0.0056 (7)
C13B0.0218 (8)0.0253 (8)0.0234 (8)0.0089 (7)0.0060 (7)0.0065 (7)
C14B0.0230 (8)0.0226 (8)0.0232 (8)0.0094 (7)0.0073 (7)0.0060 (7)
C15B0.0250 (9)0.0321 (9)0.0254 (9)0.0111 (7)0.0073 (7)0.0044 (7)
C16B0.0302 (9)0.0284 (9)0.0252 (9)0.0092 (7)0.0012 (8)0.0033 (7)
C17B0.0217 (8)0.0317 (9)0.0356 (10)0.0072 (7)0.0004 (8)0.0113 (8)
Geometric parameters (Å, º) top
S1A—C17A1.7190 (19)S1B—C17B1.7198 (18)
S1A—C14A1.7247 (17)S1B—C14B1.7281 (16)
N1A—N2A1.3739 (19)N1B—N2B1.3751 (18)
N1A—C1A1.411 (2)N1B—C1B1.413 (2)
N1A—C7A1.433 (2)N1B—C7B1.434 (2)
N2A—C13A1.285 (2)N2B—C13B1.288 (2)
C1A—C2A1.392 (2)C1B—C2B1.394 (2)
C1A—C6A1.394 (2)C1B—C6B1.395 (2)
C2A—C3A1.386 (2)C2B—C3B1.386 (2)
C2A—H2A0.95C2B—H2B0.95
C3A—C4A1.387 (3)C3B—C4B1.387 (3)
C3A—H3A0.95C3B—H3B0.95
C4A—C5A1.378 (3)C4B—C5B1.381 (3)
C4A—H4A0.95C4B—H4B0.95
C5A—C6A1.390 (2)C5B—C6B1.386 (2)
C5A—H5A0.95C5B—H5B0.95
C6A—H6A0.95C6B—H6B0.95
C7A—C8A1.383 (2)C7B—C8B1.384 (2)
C7A—C12A1.387 (2)C7B—C12B1.386 (2)
C8A—C9A1.384 (2)C8B—C9B1.385 (2)
C8A—H8A0.95C8B—H8B0.95
C9A—C10A1.379 (3)C9B—C10B1.382 (2)
C9A—H9A0.95C9B—H9B0.95
C10A—C11A1.379 (3)C10B—C11B1.387 (2)
C10A—H10A0.95C10B—H10B0.95
C11A—C12A1.388 (2)C11B—C12B1.387 (2)
C11A—H11A0.95C11B—H11B0.95
C12A—H12A0.95C12B—H12B0.95
C13A—C14A1.445 (2)C13B—C14B1.445 (2)
C13A—H13A0.95C13B—H13B0.95
C14A—C15A1.367 (2)C14B—C15B1.369 (2)
C15A—C16A1.414 (2)C15B—C16B1.413 (2)
C15A—H15A0.95C15B—H15B0.95
C16A—C17A1.345 (3)C16B—C17B1.348 (3)
C16A—H16A0.95C16B—H16B0.95
C17A—H17A0.95C17B—H17B0.95
C17A—S1A—C14A91.75 (9)C17B—S1B—C14B91.65 (8)
N2A—N1A—C1A116.17 (13)N2B—N1B—C1B116.88 (13)
N2A—N1A—C7A122.29 (13)N2B—N1B—C7B121.16 (12)
C1A—N1A—C7A121.09 (13)C1B—N1B—C7B121.74 (13)
C13A—N2A—N1A119.40 (14)C13B—N2B—N1B118.81 (13)
C2A—C1A—C6A119.30 (15)C2B—C1B—C6B119.38 (15)
C2A—C1A—N1A120.86 (15)C2B—C1B—N1B121.00 (15)
C6A—C1A—N1A119.83 (15)C6B—C1B—N1B119.62 (14)
C3A—C2A—C1A119.70 (16)C3B—C2B—C1B119.53 (16)
C3A—C2A—H2A120.1C3B—C2B—H2B120.2
C1A—C2A—H2A120.1C1B—C2B—H2B120.2
C2A—C3A—C4A121.05 (17)C2B—C3B—C4B121.33 (16)
C2A—C3A—H3A119.5C2B—C3B—H3B119.3
C4A—C3A—H3A119.5C4B—C3B—H3B119.3
C5A—C4A—C3A119.19 (16)C5B—C4B—C3B118.76 (16)
C5A—C4A—H4A120.4C5B—C4B—H4B120.6
C3A—C4A—H4A120.4C3B—C4B—H4B120.6
C4A—C5A—C6A120.59 (17)C4B—C5B—C6B120.98 (17)
C4A—C5A—H5A119.7C4B—C5B—H5B119.5
C6A—C5A—H5A119.7C6B—C5B—H5B119.5
C5A—C6A—C1A120.16 (16)C5B—C6B—C1B119.99 (16)
C5A—C6A—H6A119.9C5B—C6B—H6B120
C1A—C6A—H6A119.9C1B—C6B—H6B120
C8A—C7A—C12A120.14 (15)C8B—C7B—C12B120.21 (15)
C8A—C7A—N1A120.52 (15)C8B—C7B—N1B120.15 (14)
C12A—C7A—N1A119.34 (14)C12B—C7B—N1B119.57 (14)
C7A—C8A—C9A119.80 (16)C7B—C8B—C9B119.86 (15)
C7A—C8A—H8A120.1C7B—C8B—H8B120.1
C9A—C8A—H8A120.1C9B—C8B—H8B120.1
C10A—C9A—C8A120.23 (16)C10B—C9B—C8B120.13 (15)
C10A—C9A—H9A119.9C10B—C9B—H9B119.9
C8A—C9A—H9A119.9C8B—C9B—H9B119.9
C11A—C10A—C9A120.12 (16)C9B—C10B—C11B120.04 (15)
C11A—C10A—H10A119.9C9B—C10B—H10B120
C9A—C10A—H10A119.9C11B—C10B—H10B120
C10A—C11A—C12A120.06 (16)C12B—C11B—C10B119.91 (16)
C10A—C11A—H11A120C12B—C11B—H11B120
C12A—C11A—H11A120C10B—C11B—H11B120
C7A—C12A—C11A119.65 (15)C7B—C12B—C11B119.83 (15)
C7A—C12A—H12A120.2C7B—C12B—H12B120.1
C11A—C12A—H12A120.2C11B—C12B—H12B120.1
N2A—C13A—C14A120.29 (15)N2B—C13B—C14B120.34 (15)
N2A—C13A—H13A119.9N2B—C13B—H13B119.8
C14A—C13A—H13A119.9C14B—C13B—H13B119.8
C15A—C14A—C13A126.66 (16)C15B—C14B—C13B126.43 (15)
C15A—C14A—S1A110.41 (13)C15B—C14B—S1B110.52 (12)
C13A—C14A—S1A122.92 (13)C13B—C14B—S1B123.05 (12)
C14A—C15A—C16A113.27 (16)C14B—C15B—C16B113.16 (15)
C14A—C15A—H15A123.4C14B—C15B—H15B123.4
C16A—C15A—H15A123.4C16B—C15B—H15B123.4
C17A—C16A—C15A112.64 (16)C17B—C16B—C15B112.77 (16)
C17A—C16A—H16A123.7C17B—C16B—H16B123.6
C15A—C16A—H16A123.7C15B—C16B—H16B123.6
C16A—C17A—S1A111.92 (13)C16B—C17B—S1B111.90 (13)
C16A—C17A—H17A124C16B—C17B—H17B124.1
S1A—C17A—H17A124S1B—C17B—H17B124.1
C1A—N1A—N2A—C13A171.50 (14)C1B—N1B—N2B—C13B172.48 (14)
C7A—N1A—N2A—C13A0.8 (2)C7B—N1B—N2B—C13B2.2 (2)
N2A—N1A—C1A—C2A19.8 (2)N2B—N1B—C1B—C2B17.7 (2)
C7A—N1A—C1A—C2A167.71 (15)C7B—N1B—C1B—C2B167.66 (14)
N2A—N1A—C1A—C6A159.52 (14)N2B—N1B—C1B—C6B161.46 (14)
C7A—N1A—C1A—C6A12.9 (2)C7B—N1B—C1B—C6B13.2 (2)
C6A—C1A—C2A—C3A0.2 (2)C6B—C1B—C2B—C3B1.4 (2)
N1A—C1A—C2A—C3A179.22 (15)N1B—C1B—C2B—C3B179.43 (15)
C1A—C2A—C3A—C4A0.2 (3)C1B—C2B—C3B—C4B0.1 (3)
C2A—C3A—C4A—C5A0.2 (3)C2B—C3B—C4B—C5B1.5 (3)
C3A—C4A—C5A—C6A0.1 (3)C3B—C4B—C5B—C6B1.3 (3)
C4A—C5A—C6A—C1A0.0 (3)C4B—C5B—C6B—C1B0.3 (3)
C2A—C1A—C6A—C5A0.0 (2)C2B—C1B—C6B—C5B1.6 (2)
N1A—C1A—C6A—C5A179.33 (15)N1B—C1B—C6B—C5B179.22 (15)
N2A—N1A—C7A—C8A75.1 (2)N2B—N1B—C7B—C8B83.36 (19)
C1A—N1A—C7A—C8A96.82 (19)C1B—N1B—C7B—C8B91.07 (19)
N2A—N1A—C7A—C12A103.95 (18)N2B—N1B—C7B—C12B93.54 (18)
C1A—N1A—C7A—C12A84.1 (2)C1B—N1B—C7B—C12B92.03 (19)
C12A—C7A—C8A—C9A0.5 (2)C12B—C7B—C8B—C9B0.2 (2)
N1A—C7A—C8A—C9A179.57 (15)N1B—C7B—C8B—C9B177.12 (14)
C7A—C8A—C9A—C10A0.1 (3)C7B—C8B—C9B—C10B0.3 (2)
C8A—C9A—C10A—C11A0.4 (3)C8B—C9B—C10B—C11B0.3 (3)
C9A—C10A—C11A—C12A0.0 (3)C9B—C10B—C11B—C12B0.0 (3)
C8A—C7A—C12A—C11A0.9 (2)C8B—C7B—C12B—C11B0.0 (2)
N1A—C7A—C12A—C11A179.96 (15)N1B—C7B—C12B—C11B176.93 (14)
C10A—C11A—C12A—C7A0.6 (2)C10B—C11B—C12B—C7B0.1 (2)
N1A—N2A—C13A—C14A179.61 (14)N1B—N2B—C13B—C14B179.59 (13)
N2A—C13A—C14A—C15A169.63 (17)N2B—C13B—C14B—C15B173.46 (16)
N2A—C13A—C14A—S1A9.3 (2)N2B—C13B—C14B—S1B6.5 (2)
C17A—S1A—C14A—C15A0.57 (14)C17B—S1B—C14B—C15B0.43 (13)
C17A—S1A—C14A—C13A178.54 (15)C17B—S1B—C14B—C13B179.51 (14)
C13A—C14A—C15A—C16A178.07 (16)C13B—C14B—C15B—C16B179.54 (15)
S1A—C14A—C15A—C16A1.0 (2)S1B—C14B—C15B—C16B0.40 (19)
C14A—C15A—C16A—C17A1.0 (2)C14B—C15B—C16B—C17B0.1 (2)
C15A—C16A—C17A—S1A0.6 (2)C15B—C16B—C17B—S1B0.2 (2)
C14A—S1A—C17A—C16A0.00 (14)C14B—S1B—C17B—C16B0.35 (14)
Hydrogen-bond geometry (Å, º) top
Cg2, Cg3, Cg5 and Cg6 are the centroids of the C1A–C6A, C7A–C12A, C1B–C6B and C7B–C12B phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
C3A—H3A···Cg5i0.952.763.553 (2)141
C8A—H8A···Cg2ii0.952.973.740 (2)139
C15B—H15B···Cg2iii0.952.603.484 (2)156
C16A—H16A···Cg6iv0.952.723.5725 (19)150
C16B—H16B···Cg3v0.952.803.659 (2)151
Symmetry codes: (i) x1, y, z; (ii) x, y, z+1; (iii) x+1, y, z; (iv) x+2, y+1, z+1; (v) x, y, z1.
Hydrogen-bond geometry (Å, º) top
Cg2, Cg3, Cg5 and Cg6 are the centroids of the C1A–C6A, C7A–C12A, C1B–C6B and C7B–C12B phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
C3A—H3A···Cg5i0.952.763.553 (2)141
C8A—H8A···Cg2ii0.952.973.740 (2)139
C15B—H15B···Cg2iii0.952.603.484 (2)156
C16A—H16A···Cg6iv0.952.723.5725 (19)150
C16B—H16B···Cg3v0.952.803.659 (2)151
Symmetry codes: (i) x1, y, z; (ii) x, y, z+1; (iii) x+1, y, z; (iv) x+2, y+1, z+1; (v) x, y, z1.
Acknowledgements top

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
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