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metal-organic compounds
Benzyl 5-ferrocenyl-3-(4-methylphenyl)-2-pyrazoline-1-dithiocarboxylate
aCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People's Republic of China
*Correspondence e-mail: yhliuyzu@yahoo.com.cn
In the title compound, [Fe(C5H5)(C23H21N2S2)], the cyclopentadienyl rings of the ferrocenyl unit deviate slightly from the eclipsed form. In the pyrazoline ring, the N atom bonded to S-benzyl dithiocarbazate exhibits unconventional sp2-hybrid character in order to form an extended The pyrazoline ring displays an The molecules are linked into chains along the b axis via C—H⋯S intermolecular hydrogen bonds.
Related literature
For related literature, see: Fahrni et al. (2003); Huang & Katzenellenbogen (2000
); Huang et al. (1998
); Liu et al. (2007
); Rivett et al. (1979
); Shi et al. (2004
); Sun et al. (2004
); Wiley et al. (1958
); Wilkinson et al. (1990
).
Experimental
Crystal data
|
Data collection: SMART (Bruker, 2002); cell SAINT (Bruker, 2002
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990
); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997
); molecular graphics: PLATON (Spek, 2003
); software used to prepare material for publication: SHELXTL (Bruker, 2002
).
Supporting information
https://doi.org/10.1107/S1600536807066536/pv2048sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807066536/pv2048Isup2.hkl
The title compound was synthesized by refluxing an absolute ethanol solution of 1-(4-methylphenyl)-3-ferrocenylprop-2-en-1-one (3.30 g, 10 mmol) and S-benzyldithiocarbazate (1.98 g, 10 mmol) for 24 h. After refrigeration (278 K) of the solution for 10 h, yellow pricipite separated out and recrystallized from a mixture of 1,2-dichloroethane and petroleum ether (5:1 volume ratio) (3.1 g, yield 61%). The yellow crystals suitable for X-ray analysis were obtained by slow evaporation of a dichloromethane solution at 278 K.
All H atoms were fixed geometrically at ideal positions and allowed to ride on the parent atoms with C—H distances 0.96, 0.97, 0.98 and 0.93 Å for CH3, CH2, CH and aromatic CH groups, respectively, and with Uiso(H) values of 1.2 and 1.5 times Ueq(C) for the nonmethyl and methyl groups, respectively.
Pyrazoline derivatives are an important class of conjugated fluorescent dyes emitting blue fluorescence and have been extensively applied in the industry due to the high fluorescence
(Wilkinson et al., 1990; Rivett et al., 1979). For example, pyrazolines have been widely used as optical brightening agents for textiles, paper and fabrics and as a hole-conveying medium in photoconductive materials (Sun et al., 2004; Huang & Katzenellenbogen, 2000; Wiley et al., 1958). We found that ferrocene derivatives have good properties of fluorescence and coordination chemistry with many metal ions (Huang et al., 1998; Shi et al., 2004). Continuing our research (Liu et al., 2007) we report the synthesis and structure of the title compound, (I).In the structure of (I), the substituted ring (Cps) and unsubstituted ring (Cp) of the ferrocenyl moiety are slightly deprived from eclipsed form, with the five pseudo-torsion angles in the range 10.5 (2) — 10.9 (3)°. The distances from central Fe(II) ion to Cps center [Cg(1)] and to Cp center [Cg(2)] are 1.651 (3) Å and 1.656 (2) Å, respectively. The angle Cg(1)–Fe–Cg(2) is 177.9 (3)° and the central Fe(II) ion is located almost in the middle of the two cyclopentadiene rings which are not parallel because their dihedral angle is 2.3 (4)° (Fig. 1).
In the pyrazolinyl ring, the C=N and C–N bond lengths are in agreement with those found in similar structures (Fahrni et al., 2003). However, the N–N bond length is longer than those found in the above-cited structures. But the bond distance of C21–N1 is shorter than a C–N single bond and slight longer than a C=N double bond. It might contribute to unclassical sp2-hybrid N1 atom which is evident from the sum of the three angles around the N1 atom being 360° (Table 1) and that atoms C21, N1, N2 and C13 are co-planar. Furthemore, atoms S2, C21, N1, N2, C13 along with adjacent phenyl ring result in a large cojugated system.
In its packing diagram, the molecules of (I) are linked into two invers chains via C— H···S intermolecular hydrogen-bonds with C···S distance 3.583 (3) Å and C26—H26···S2 angle 142°, along the b axis (Fig. 2, Table 2).
For related literature, see: Fahrni et al. (2003); Huang & Katzenellenbogen (2000); Huang et al. (1998); Liu et al. (2007); Rivett et al. (1979); Shi et al. (2004); Sun et al. (2004); Wiley et al. (1958); Wilkinson et al. (1990).
Data collection: SMART (Bruker, 2002); cell
SMART (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2002).[Fe(C5H5)(C23H21N2S2)] | Z = 2 |
Mr = 510.50 | F(000) = 532.0 |
Triclinic, P1 | Dx = 1.396 Mg m−3 |
Hall symbol: - P 1 | Melting point: 345(2) K |
a = 9.178 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.468 (2) Å | Cell parameters from 7052 reflections |
c = 13.216 (2) Å | θ = 2.3–27.6° |
α = 99.37 (1)° | µ = 0.81 mm−1 |
β = 101.55 (2)° | T = 296 K |
γ = 96.12 (1)° | Block, yellow |
V = 1214.6 (3) Å3 | 0.33 × 0.31 × 0.28 mm |
Bruker SMART APEX CCD area-detector diffractometer | 5528 independent reflections |
Radiation source: fine-focus sealed tube | 5035 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
φ and ω scans | θmax = 27.7°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −10→10 |
Tmin = 0.776, Tmax = 0.805 | k = −12→12 |
10742 measured reflections | l = −15→15 |
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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0552P)2 + 0.4985P] where P = (Fo2 + 2Fc2)/3 |
5528 reflections | (Δ/σ)max = 0.007 |
299 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
[Fe(C5H5)(C23H21N2S2)] | γ = 96.12 (1)° |
Mr = 510.50 | V = 1214.6 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.178 (1) Å | Mo Kα radiation |
b = 10.468 (2) Å | µ = 0.81 mm−1 |
c = 13.216 (2) Å | T = 296 K |
α = 99.37 (1)° | 0.33 × 0.31 × 0.28 mm |
β = 101.55 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 5528 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 5035 reflections with I > 2σ(I) |
Tmin = 0.776, Tmax = 0.805 | Rint = 0.019 |
10742 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.44 e Å−3 |
5528 reflections | Δρmin = −0.22 e Å−3 |
299 parameters |
Experimental. Analysis calculated for C18H16N4OS2: C 65.87, H 5.13, N 5.49%; found: C 65.82, H 5.11, N 5.51%. IR (KBr, cm-1): ν(C=N), ν(S=C) and ν(N–N) 1559 (m), 1245 (s) and 1037 (w) cm-1. 1H NMR (600 MHz, CDCl3,δ, p.p.m.): 7.23–7.76 (m, 9H, ArH), 6.04 (broad, 1H, CH), 4.50–4.47 (d, 1H, CH2), 4.41–4.39 (d, 1H, CH2), 4.15 (s, 5H, C5H5), 4.03 (s, 1H, C5H4), 4.12 (s, 1H, C5H4), 4.19 (s, 1H, C5H4), 4.71 (s, 1H, C5H4), 3.72 (s, 2H, ArCH2), 2.41 (s, 3H, CH3) p.p.m.. |
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. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.56551 (3) | −0.22018 (2) | 0.364537 (18) | 0.02183 (10) | |
S1 | 0.64012 (5) | 0.30267 (4) | 0.12369 (4) | 0.02864 (13) | |
S2 | 0.72753 (5) | 0.03133 (4) | 0.06920 (3) | 0.02501 (12) | |
N1 | 0.52328 (15) | 0.09334 (13) | 0.17619 (11) | 0.0209 (3) | |
N2 | 0.43248 (16) | 0.18040 (13) | 0.21361 (11) | 0.0219 (3) | |
C5 | 0.3598 (2) | −0.28594 (18) | 0.38988 (16) | 0.0310 (4) | |
H5 | 0.2866 | −0.2347 | 0.4034 | 0.037* | |
C4 | 0.4760 (2) | −0.31695 (18) | 0.46642 (16) | 0.0322 (4) | |
H4 | 0.4920 | −0.2897 | 0.5388 | 0.039* | |
C3 | 0.5633 (2) | −0.39647 (18) | 0.41353 (16) | 0.0342 (4) | |
H3 | 0.6465 | −0.4305 | 0.4452 | 0.041* | |
C2 | 0.5017 (2) | −0.41532 (18) | 0.30377 (16) | 0.0351 (4) | |
H2 | 0.5376 | −0.4637 | 0.2509 | 0.042* | |
C1 | 0.3750 (2) | −0.34678 (18) | 0.28908 (16) | 0.0324 (4) | |
H1 | 0.3133 | −0.3427 | 0.2250 | 0.039* | |
C6 | 0.6003 (2) | −0.01980 (17) | 0.39096 (14) | 0.0262 (4) | |
H6 | 0.5385 | 0.0357 | 0.4175 | 0.031* | |
C7 | 0.7219 (2) | −0.06716 (19) | 0.45157 (15) | 0.0340 (4) | |
H7 | 0.7534 | −0.0483 | 0.5245 | 0.041* | |
C8 | 0.7865 (2) | −0.1481 (2) | 0.38121 (17) | 0.0365 (5) | |
H8 | 0.8680 | −0.1917 | 0.4001 | 0.044* | |
C9 | 0.7059 (2) | −0.15140 (18) | 0.27690 (15) | 0.0287 (4) | |
H9 | 0.7257 | −0.1972 | 0.2158 | 0.034* | |
C10 | 0.58923 (19) | −0.07210 (16) | 0.28218 (13) | 0.0218 (3) | |
C11 | 0.47914 (18) | −0.04276 (16) | 0.19133 (13) | 0.0212 (3) | |
H11 | 0.4742 | −0.1063 | 0.1271 | 0.025* | |
C12 | 0.32107 (19) | −0.03292 (16) | 0.21151 (14) | 0.0230 (4) | |
H12A | 0.2439 | −0.0746 | 0.1500 | 0.028* | |
H12B | 0.3063 | −0.0725 | 0.2708 | 0.028* | |
C13 | 0.31983 (18) | 0.11285 (16) | 0.23500 (12) | 0.0211 (3) | |
C14 | 0.20317 (18) | 0.17603 (17) | 0.27623 (13) | 0.0219 (3) | |
C15 | 0.0737 (2) | 0.10168 (18) | 0.28749 (14) | 0.0271 (4) | |
H15 | 0.0607 | 0.0111 | 0.2677 | 0.033* | |
C16 | −0.0357 (2) | 0.16144 (19) | 0.32793 (14) | 0.0309 (4) | |
H16 | −0.1212 | 0.1103 | 0.3349 | 0.037* | |
C17 | −0.0196 (2) | 0.2960 (2) | 0.35799 (14) | 0.0309 (4) | |
C18 | 0.1102 (2) | 0.37050 (18) | 0.34690 (14) | 0.0296 (4) | |
H18 | 0.1230 | 0.4611 | 0.3671 | 0.036* | |
C19 | 0.2197 (2) | 0.31208 (17) | 0.30645 (14) | 0.0260 (4) | |
H19 | 0.3048 | 0.3635 | 0.2993 | 0.031* | |
C20 | −0.1389 (2) | 0.3607 (3) | 0.40227 (19) | 0.0483 (6) | |
H20A | −0.2364 | 0.3153 | 0.3658 | 0.072* | |
H20B | −0.1313 | 0.4502 | 0.3934 | 0.072* | |
H20C | −0.1246 | 0.3576 | 0.4758 | 0.072* | |
C21 | 0.62648 (18) | 0.13289 (16) | 0.12474 (13) | 0.0210 (3) | |
C22 | 0.7966 (2) | 0.32849 (18) | 0.06058 (17) | 0.0356 (5) | |
H22A | 0.8841 | 0.2976 | 0.0978 | 0.043* | |
H22B | 0.7706 | 0.2810 | −0.0115 | 0.043* | |
C23 | 0.8295 (2) | 0.47341 (17) | 0.06311 (14) | 0.0263 (4) | |
C28 | 0.7407 (2) | 0.5341 (2) | −0.00745 (16) | 0.0370 (5) | |
H28 | 0.6566 | 0.4858 | −0.0549 | 0.044* | |
C27 | 0.7770 (3) | 0.6667 (2) | −0.00738 (18) | 0.0442 (5) | |
H27 | 0.7181 | 0.7062 | −0.0557 | 0.053* | |
C26 | 0.8997 (2) | 0.73954 (19) | 0.06398 (19) | 0.0405 (5) | |
H26 | 0.9246 | 0.8279 | 0.0636 | 0.049* | |
C25 | 0.9849 (2) | 0.6807 (2) | 0.13578 (19) | 0.0408 (5) | |
H25 | 1.0664 | 0.7300 | 0.1853 | 0.049* | |
C24 | 0.9504 (2) | 0.54858 (19) | 0.13486 (17) | 0.0344 (4) | |
H24 | 1.0097 | 0.5098 | 0.1834 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.02452 (15) | 0.02086 (15) | 0.02275 (15) | 0.00548 (10) | 0.00666 (11) | 0.00855 (10) |
S1 | 0.0313 (2) | 0.0201 (2) | 0.0413 (3) | 0.00543 (17) | 0.0205 (2) | 0.00872 (19) |
S2 | 0.0281 (2) | 0.0247 (2) | 0.0256 (2) | 0.00900 (17) | 0.01053 (18) | 0.00548 (17) |
N1 | 0.0250 (7) | 0.0185 (7) | 0.0220 (7) | 0.0066 (5) | 0.0085 (6) | 0.0057 (5) |
N2 | 0.0242 (7) | 0.0224 (7) | 0.0221 (7) | 0.0077 (6) | 0.0085 (6) | 0.0064 (6) |
C5 | 0.0291 (9) | 0.0274 (9) | 0.0412 (11) | 0.0029 (7) | 0.0142 (8) | 0.0125 (8) |
C4 | 0.0403 (11) | 0.0297 (10) | 0.0319 (10) | 0.0035 (8) | 0.0138 (8) | 0.0148 (8) |
C3 | 0.0408 (11) | 0.0239 (9) | 0.0443 (12) | 0.0099 (8) | 0.0121 (9) | 0.0180 (8) |
C2 | 0.0442 (11) | 0.0213 (9) | 0.0415 (11) | 0.0056 (8) | 0.0147 (9) | 0.0040 (8) |
C1 | 0.0332 (10) | 0.0254 (9) | 0.0361 (11) | −0.0019 (8) | 0.0038 (8) | 0.0075 (8) |
C6 | 0.0326 (9) | 0.0209 (8) | 0.0240 (9) | 0.0000 (7) | 0.0053 (7) | 0.0049 (7) |
C7 | 0.0351 (10) | 0.0348 (10) | 0.0268 (10) | −0.0067 (8) | −0.0032 (8) | 0.0108 (8) |
C8 | 0.0236 (9) | 0.0423 (11) | 0.0481 (12) | 0.0062 (8) | 0.0046 (8) | 0.0248 (10) |
C9 | 0.0270 (9) | 0.0308 (10) | 0.0356 (10) | 0.0082 (7) | 0.0144 (8) | 0.0153 (8) |
C10 | 0.0239 (8) | 0.0201 (8) | 0.0239 (9) | 0.0021 (6) | 0.0076 (7) | 0.0092 (7) |
C11 | 0.0268 (9) | 0.0172 (8) | 0.0205 (8) | 0.0040 (6) | 0.0059 (7) | 0.0049 (6) |
C12 | 0.0229 (8) | 0.0213 (8) | 0.0254 (9) | 0.0027 (6) | 0.0045 (7) | 0.0071 (7) |
C13 | 0.0228 (8) | 0.0230 (8) | 0.0175 (8) | 0.0027 (7) | 0.0024 (6) | 0.0070 (6) |
C14 | 0.0220 (8) | 0.0265 (9) | 0.0182 (8) | 0.0054 (7) | 0.0035 (6) | 0.0069 (7) |
C15 | 0.0267 (9) | 0.0270 (9) | 0.0270 (9) | 0.0011 (7) | 0.0051 (7) | 0.0059 (7) |
C16 | 0.0214 (9) | 0.0424 (11) | 0.0280 (9) | −0.0021 (8) | 0.0073 (7) | 0.0060 (8) |
C17 | 0.0268 (9) | 0.0444 (11) | 0.0221 (9) | 0.0080 (8) | 0.0075 (7) | 0.0032 (8) |
C18 | 0.0331 (10) | 0.0283 (9) | 0.0277 (9) | 0.0078 (8) | 0.0082 (8) | 0.0020 (7) |
C19 | 0.0250 (9) | 0.0260 (9) | 0.0287 (9) | 0.0034 (7) | 0.0084 (7) | 0.0074 (7) |
C20 | 0.0334 (11) | 0.0616 (15) | 0.0477 (13) | 0.0092 (10) | 0.0175 (10) | −0.0079 (11) |
C21 | 0.0222 (8) | 0.0217 (8) | 0.0190 (8) | 0.0035 (6) | 0.0030 (6) | 0.0054 (6) |
C22 | 0.0384 (11) | 0.0265 (10) | 0.0497 (12) | 0.0037 (8) | 0.0282 (9) | 0.0076 (9) |
C23 | 0.0271 (9) | 0.0252 (9) | 0.0320 (10) | 0.0048 (7) | 0.0171 (8) | 0.0077 (7) |
C28 | 0.0345 (10) | 0.0428 (12) | 0.0327 (11) | 0.0070 (9) | 0.0050 (8) | 0.0066 (9) |
C27 | 0.0503 (13) | 0.0474 (13) | 0.0487 (13) | 0.0257 (11) | 0.0184 (10) | 0.0276 (10) |
C26 | 0.0370 (11) | 0.0266 (10) | 0.0701 (15) | 0.0109 (8) | 0.0301 (11) | 0.0178 (10) |
C25 | 0.0266 (10) | 0.0321 (11) | 0.0620 (14) | 0.0017 (8) | 0.0098 (9) | 0.0055 (10) |
C24 | 0.0290 (10) | 0.0342 (10) | 0.0439 (11) | 0.0074 (8) | 0.0086 (8) | 0.0159 (9) |
Fe1—C8 | 2.0428 (19) | C10—C11 | 1.502 (2) |
Fe1—C2 | 2.0452 (19) | C11—C12 | 1.538 (2) |
Fe1—C1 | 2.0460 (19) | C11—H11 | 0.9800 |
Fe1—C9 | 2.0474 (18) | C12—C13 | 1.509 (2) |
Fe1—C6 | 2.0488 (17) | C12—H12A | 0.9700 |
Fe1—C7 | 2.0487 (19) | C12—H12B | 0.9700 |
Fe1—C5 | 2.0493 (18) | C13—C14 | 1.466 (2) |
Fe1—C10 | 2.0510 (16) | C14—C15 | 1.397 (2) |
Fe1—C3 | 2.0521 (18) | C14—C19 | 1.398 (2) |
Fe1—C4 | 2.0549 (18) | C15—C16 | 1.388 (3) |
S1—C21 | 1.7708 (17) | C15—H15 | 0.9300 |
S1—C22 | 1.8167 (18) | C16—C17 | 1.383 (3) |
S2—C21 | 1.6608 (17) | C16—H16 | 0.9300 |
N1—C21 | 1.340 (2) | C17—C18 | 1.399 (3) |
N1—N2 | 1.3964 (19) | C17—C20 | 1.512 (3) |
N1—C11 | 1.495 (2) | C18—C19 | 1.382 (3) |
N2—C13 | 1.294 (2) | C18—H18 | 0.9300 |
C5—C1 | 1.420 (3) | C19—H19 | 0.9300 |
C5—C4 | 1.419 (3) | C20—H20A | 0.9600 |
C5—H5 | 0.9300 | C20—H20B | 0.9600 |
C4—C3 | 1.414 (3) | C20—H20C | 0.9600 |
C4—H4 | 0.9300 | C22—C23 | 1.508 (2) |
C3—C2 | 1.420 (3) | C22—H22A | 0.9700 |
C3—H3 | 0.9300 | C22—H22B | 0.9700 |
C2—C1 | 1.428 (3) | C23—C24 | 1.378 (3) |
C2—H2 | 0.9300 | C23—C28 | 1.392 (3) |
C1—H1 | 0.9300 | C28—C27 | 1.392 (3) |
C6—C7 | 1.422 (3) | C28—H28 | 0.9300 |
C6—C10 | 1.432 (2) | C27—C26 | 1.377 (3) |
C6—H6 | 0.9300 | C27—H27 | 0.9300 |
C7—C8 | 1.416 (3) | C26—C25 | 1.374 (3) |
C7—H7 | 0.9300 | C26—H26 | 0.9300 |
C8—C9 | 1.421 (3) | C25—C24 | 1.383 (3) |
C8—H8 | 0.9300 | C25—H25 | 0.9300 |
C9—C10 | 1.429 (2) | C24—H24 | 0.9300 |
C9—H9 | 0.9300 | ||
C8—Fe1—C2 | 116.95 (9) | C6—C7—Fe1 | 69.69 (10) |
C8—Fe1—C1 | 151.92 (9) | C8—C7—H7 | 126.1 |
C2—Fe1—C1 | 40.85 (8) | C6—C7—H7 | 126.1 |
C8—Fe1—C9 | 40.66 (8) | Fe1—C7—H7 | 126.3 |
C2—Fe1—C9 | 106.49 (8) | C7—C8—C9 | 108.51 (17) |
C1—Fe1—C9 | 118.79 (8) | C7—C8—Fe1 | 69.98 (11) |
C8—Fe1—C6 | 68.20 (8) | C9—C8—Fe1 | 69.85 (10) |
C2—Fe1—C6 | 166.18 (8) | C7—C8—H8 | 125.7 |
C1—Fe1—C6 | 129.18 (7) | C9—C8—H8 | 125.7 |
C9—Fe1—C6 | 68.42 (7) | Fe1—C8—H8 | 126.0 |
C8—Fe1—C7 | 40.49 (9) | C8—C9—C10 | 108.07 (17) |
C2—Fe1—C7 | 151.03 (8) | C8—C9—Fe1 | 69.49 (11) |
C1—Fe1—C7 | 166.78 (8) | C10—C9—Fe1 | 69.73 (9) |
C9—Fe1—C7 | 68.41 (8) | C8—C9—H9 | 126.0 |
C6—Fe1—C7 | 40.62 (8) | C10—C9—H9 | 126.0 |
C8—Fe1—C5 | 164.95 (8) | Fe1—C9—H9 | 126.4 |
C2—Fe1—C5 | 68.37 (8) | C9—C10—C6 | 107.23 (15) |
C1—Fe1—C5 | 40.57 (8) | C9—C10—C11 | 127.04 (15) |
C9—Fe1—C5 | 153.95 (8) | C6—C10—C11 | 125.67 (15) |
C6—Fe1—C5 | 110.18 (7) | C9—C10—Fe1 | 69.46 (9) |
C7—Fe1—C5 | 128.59 (8) | C6—C10—Fe1 | 69.47 (9) |
C8—Fe1—C10 | 68.59 (7) | C11—C10—Fe1 | 128.36 (11) |
C2—Fe1—C10 | 127.05 (8) | N1—C11—C10 | 109.61 (13) |
C1—Fe1—C10 | 108.77 (7) | N1—C11—C12 | 100.44 (12) |
C9—Fe1—C10 | 40.81 (7) | C10—C11—C12 | 114.22 (14) |
C6—Fe1—C10 | 40.88 (7) | N1—C11—H11 | 110.7 |
C7—Fe1—C10 | 68.72 (7) | C10—C11—H11 | 110.7 |
C5—Fe1—C10 | 120.71 (7) | C12—C11—H11 | 110.7 |
C8—Fe1—C3 | 106.16 (8) | C13—C12—C11 | 102.75 (13) |
C2—Fe1—C3 | 40.56 (8) | C13—C12—H12A | 111.2 |
C1—Fe1—C3 | 68.31 (8) | C11—C12—H12A | 111.2 |
C9—Fe1—C3 | 125.60 (8) | C13—C12—H12B | 111.2 |
C6—Fe1—C3 | 152.81 (8) | C11—C12—H12B | 111.2 |
C7—Fe1—C3 | 117.78 (8) | H12A—C12—H12B | 109.1 |
C5—Fe1—C3 | 68.04 (8) | N2—C13—C14 | 121.50 (15) |
C10—Fe1—C3 | 164.02 (8) | N2—C13—C12 | 113.60 (15) |
C8—Fe1—C4 | 126.35 (8) | C14—C13—C12 | 124.88 (14) |
C2—Fe1—C4 | 68.10 (8) | C15—C14—C19 | 118.43 (16) |
C1—Fe1—C4 | 68.15 (8) | C15—C14—C13 | 120.79 (15) |
C9—Fe1—C4 | 163.37 (8) | C19—C14—C13 | 120.77 (15) |
C6—Fe1—C4 | 120.38 (8) | C16—C15—C14 | 120.77 (17) |
C7—Fe1—C4 | 108.22 (8) | C16—C15—H15 | 119.6 |
C5—Fe1—C4 | 40.46 (8) | C14—C15—H15 | 119.6 |
C10—Fe1—C4 | 154.75 (7) | C17—C16—C15 | 120.92 (17) |
C3—Fe1—C4 | 40.27 (8) | C17—C16—H16 | 119.5 |
C21—S1—C22 | 101.89 (8) | C15—C16—H16 | 119.5 |
C21—N1—N2 | 120.26 (13) | C16—C17—C18 | 118.34 (17) |
C21—N1—C11 | 127.22 (14) | C16—C17—C20 | 120.75 (18) |
N2—N1—C11 | 112.25 (12) | C18—C17—C20 | 120.91 (19) |
C13—N2—N1 | 108.02 (13) | C19—C18—C17 | 121.25 (17) |
C1—C5—C4 | 108.06 (17) | C19—C18—H18 | 119.4 |
C1—C5—Fe1 | 69.59 (11) | C17—C18—H18 | 119.4 |
C4—C5—Fe1 | 69.98 (11) | C18—C19—C14 | 120.30 (16) |
C1—C5—H5 | 126.0 | C18—C19—H19 | 119.9 |
C4—C5—H5 | 126.0 | C14—C19—H19 | 119.9 |
Fe1—C5—H5 | 126.0 | C17—C20—H20A | 109.5 |
C3—C4—C5 | 108.19 (17) | C17—C20—H20B | 109.5 |
C3—C4—Fe1 | 69.76 (10) | H20A—C20—H20B | 109.5 |
C5—C4—Fe1 | 69.56 (10) | C17—C20—H20C | 109.5 |
C3—C4—H4 | 125.9 | H20A—C20—H20C | 109.5 |
C5—C4—H4 | 125.9 | H20B—C20—H20C | 109.5 |
Fe1—C4—H4 | 126.4 | N1—C21—S2 | 122.65 (13) |
C4—C3—C2 | 108.20 (17) | N1—C21—S1 | 112.19 (12) |
C4—C3—Fe1 | 69.97 (10) | S2—C21—S1 | 125.16 (10) |
C2—C3—Fe1 | 69.46 (10) | C23—C22—S1 | 107.43 (12) |
C4—C3—H3 | 125.9 | C23—C22—H22A | 110.2 |
C2—C3—H3 | 125.9 | S1—C22—H22A | 110.2 |
Fe1—C3—H3 | 126.2 | C23—C22—H22B | 110.2 |
C3—C2—C1 | 107.78 (18) | S1—C22—H22B | 110.2 |
C3—C2—Fe1 | 69.98 (11) | H22A—C22—H22B | 108.5 |
C1—C2—Fe1 | 69.60 (10) | C24—C23—C28 | 118.41 (17) |
C3—C2—H2 | 126.1 | C24—C23—C22 | 120.43 (17) |
C1—C2—H2 | 126.1 | C28—C23—C22 | 121.16 (18) |
Fe1—C2—H2 | 125.9 | C23—C28—C27 | 120.40 (19) |
C5—C1—C2 | 107.77 (18) | C23—C28—H28 | 119.8 |
C5—C1—Fe1 | 69.84 (11) | C27—C28—H28 | 119.8 |
C2—C1—Fe1 | 69.54 (11) | C26—C27—C28 | 120.19 (19) |
C5—C1—H1 | 126.1 | C26—C27—H27 | 119.9 |
C2—C1—H1 | 126.1 | C28—C27—H27 | 119.9 |
Fe1—C1—H1 | 126.1 | C25—C26—C27 | 119.51 (18) |
C7—C6—C10 | 108.33 (16) | C25—C26—H26 | 120.2 |
C7—C6—Fe1 | 69.69 (10) | C27—C26—H26 | 120.2 |
C10—C6—Fe1 | 69.64 (9) | C26—C25—C24 | 120.4 (2) |
C7—C6—H6 | 125.8 | C26—C25—H25 | 119.8 |
C10—C6—H6 | 125.8 | C24—C25—H25 | 119.8 |
Fe1—C6—H6 | 126.4 | C23—C24—C25 | 121.06 (19) |
C8—C7—C6 | 107.85 (17) | C23—C24—H24 | 119.5 |
C8—C7—Fe1 | 69.53 (11) | C25—C24—H24 | 119.5 |
C21—N1—N2—C13 | 163.81 (15) | C1—Fe1—C7—C6 | −43.9 (4) |
C11—N1—N2—C13 | −10.50 (18) | C9—Fe1—C7—C6 | 81.61 (12) |
C8—Fe1—C5—C1 | −151.8 (3) | C5—Fe1—C7—C6 | −75.37 (13) |
C2—Fe1—C5—C1 | −38.01 (11) | C10—Fe1—C7—C6 | 37.61 (10) |
C9—Fe1—C5—C1 | 45.3 (2) | C3—Fe1—C7—C6 | −158.46 (11) |
C6—Fe1—C5—C1 | 127.27 (11) | C4—Fe1—C7—C6 | −115.72 (12) |
C7—Fe1—C5—C1 | 169.42 (11) | C6—C7—C8—C9 | 0.0 (2) |
C10—Fe1—C5—C1 | 83.21 (12) | Fe1—C7—C8—C9 | 59.42 (13) |
C3—Fe1—C5—C1 | −81.85 (12) | C6—C7—C8—Fe1 | −59.37 (13) |
C4—Fe1—C5—C1 | −119.19 (16) | C2—Fe1—C8—C7 | −156.34 (11) |
C8—Fe1—C5—C4 | −32.6 (3) | C1—Fe1—C8—C7 | 171.85 (15) |
C2—Fe1—C5—C4 | 81.18 (12) | C9—Fe1—C8—C7 | 119.58 (16) |
C1—Fe1—C5—C4 | 119.19 (16) | C6—Fe1—C8—C7 | 37.76 (11) |
C9—Fe1—C5—C4 | 164.52 (16) | C5—Fe1—C8—C7 | −49.0 (3) |
C6—Fe1—C5—C4 | −113.54 (12) | C10—Fe1—C8—C7 | 81.88 (12) |
C7—Fe1—C5—C4 | −71.39 (14) | C3—Fe1—C8—C7 | −114.07 (12) |
C10—Fe1—C5—C4 | −157.60 (11) | C4—Fe1—C8—C7 | −74.70 (14) |
C3—Fe1—C5—C4 | 37.34 (12) | C2—Fe1—C8—C9 | 84.08 (13) |
C1—C5—C4—C3 | 0.1 (2) | C1—Fe1—C8—C9 | 52.3 (2) |
Fe1—C5—C4—C3 | −59.26 (13) | C6—Fe1—C8—C9 | −81.83 (12) |
C1—C5—C4—Fe1 | 59.39 (12) | C7—Fe1—C8—C9 | −119.58 (16) |
C8—Fe1—C4—C3 | −70.49 (15) | C5—Fe1—C8—C9 | −168.6 (3) |
C2—Fe1—C4—C3 | 37.61 (12) | C10—Fe1—C8—C9 | −37.70 (11) |
C1—Fe1—C4—C3 | 81.79 (13) | C3—Fe1—C8—C9 | 126.35 (12) |
C9—Fe1—C4—C3 | −36.3 (3) | C4—Fe1—C8—C9 | 165.72 (11) |
C6—Fe1—C4—C3 | −154.57 (12) | C7—C8—C9—C10 | −0.2 (2) |
C7—Fe1—C4—C3 | −111.74 (13) | Fe1—C8—C9—C10 | 59.26 (12) |
C5—Fe1—C4—C3 | 119.51 (17) | C7—C8—C9—Fe1 | −59.50 (13) |
C10—Fe1—C4—C3 | 169.66 (15) | C2—Fe1—C9—C8 | −112.38 (13) |
C8—Fe1—C4—C5 | 170.00 (12) | C1—Fe1—C9—C8 | −154.87 (12) |
C2—Fe1—C4—C5 | −81.90 (13) | C6—Fe1—C9—C8 | 81.23 (13) |
C1—Fe1—C4—C5 | −37.72 (11) | C7—Fe1—C9—C8 | 37.40 (12) |
C9—Fe1—C4—C5 | −155.8 (2) | C5—Fe1—C9—C8 | 173.27 (16) |
C6—Fe1—C4—C5 | 85.92 (13) | C10—Fe1—C9—C8 | 119.41 (16) |
C7—Fe1—C4—C5 | 128.75 (12) | C3—Fe1—C9—C8 | −72.06 (15) |
C10—Fe1—C4—C5 | 50.2 (2) | C4—Fe1—C9—C8 | −44.0 (3) |
C3—Fe1—C4—C5 | −119.51 (17) | C8—Fe1—C9—C10 | −119.41 (16) |
C5—C4—C3—C2 | 0.0 (2) | C2—Fe1—C9—C10 | 128.21 (11) |
Fe1—C4—C3—C2 | −59.13 (13) | C1—Fe1—C9—C10 | 85.72 (12) |
C5—C4—C3—Fe1 | 59.14 (13) | C6—Fe1—C9—C10 | −38.18 (10) |
C8—Fe1—C3—C4 | 127.78 (12) | C7—Fe1—C9—C10 | −82.01 (11) |
C2—Fe1—C3—C4 | −119.45 (17) | C5—Fe1—C9—C10 | 53.9 (2) |
C1—Fe1—C3—C4 | −81.37 (13) | C3—Fe1—C9—C10 | 168.53 (10) |
C9—Fe1—C3—C4 | 167.97 (11) | C4—Fe1—C9—C10 | −163.4 (2) |
C6—Fe1—C3—C4 | 54.2 (2) | C8—C9—C10—C6 | 0.34 (19) |
C7—Fe1—C3—C4 | 85.70 (13) | Fe1—C9—C10—C6 | 59.45 (11) |
C5—Fe1—C3—C4 | −37.51 (12) | C8—C9—C10—C11 | 177.69 (16) |
C10—Fe1—C3—C4 | −163.8 (2) | Fe1—C9—C10—C11 | −123.19 (16) |
C8—Fe1—C3—C2 | −112.77 (13) | C8—C9—C10—Fe1 | −59.12 (12) |
C1—Fe1—C3—C2 | 38.08 (12) | C7—C6—C10—C9 | −0.31 (19) |
C9—Fe1—C3—C2 | −72.58 (14) | Fe1—C6—C10—C9 | −59.44 (11) |
C6—Fe1—C3—C2 | 173.60 (15) | C7—C6—C10—C11 | −177.71 (15) |
C7—Fe1—C3—C2 | −154.85 (12) | Fe1—C6—C10—C11 | 123.15 (16) |
C5—Fe1—C3—C2 | 81.94 (13) | C7—C6—C10—Fe1 | 59.14 (12) |
C10—Fe1—C3—C2 | −44.4 (3) | C8—Fe1—C10—C9 | 37.56 (12) |
C4—Fe1—C3—C2 | 119.45 (17) | C2—Fe1—C10—C9 | −70.73 (14) |
C4—C3—C2—C1 | −0.1 (2) | C1—Fe1—C10—C9 | −112.63 (12) |
Fe1—C3—C2—C1 | −59.58 (13) | C6—Fe1—C10—C9 | 118.56 (15) |
C4—C3—C2—Fe1 | 59.45 (13) | C7—Fe1—C10—C9 | 81.19 (12) |
C8—Fe1—C2—C3 | 83.47 (13) | C5—Fe1—C10—C9 | −155.64 (11) |
C1—Fe1—C2—C3 | −118.83 (17) | C3—Fe1—C10—C9 | −36.0 (3) |
C9—Fe1—C2—C3 | 125.99 (12) | C4—Fe1—C10—C9 | 168.95 (16) |
C6—Fe1—C2—C3 | −167.7 (3) | C8—Fe1—C10—C6 | −81.00 (12) |
C7—Fe1—C2—C3 | 50.9 (2) | C2—Fe1—C10—C6 | 170.70 (11) |
C5—Fe1—C2—C3 | −81.07 (12) | C1—Fe1—C10—C6 | 128.81 (11) |
C10—Fe1—C2—C3 | 166.04 (11) | C9—Fe1—C10—C6 | −118.56 (15) |
C4—Fe1—C2—C3 | −37.35 (12) | C7—Fe1—C10—C6 | −37.37 (11) |
C8—Fe1—C2—C1 | −157.71 (12) | C5—Fe1—C10—C6 | 85.80 (12) |
C9—Fe1—C2—C1 | −115.19 (12) | C3—Fe1—C10—C6 | −154.5 (3) |
C6—Fe1—C2—C1 | −48.9 (4) | C4—Fe1—C10—C6 | 50.4 (2) |
C7—Fe1—C2—C1 | 169.74 (15) | C8—Fe1—C10—C11 | 159.15 (17) |
C5—Fe1—C2—C1 | 37.75 (12) | C2—Fe1—C10—C11 | 50.85 (18) |
C10—Fe1—C2—C1 | −75.14 (14) | C1—Fe1—C10—C11 | 8.96 (17) |
C3—Fe1—C2—C1 | 118.83 (17) | C9—Fe1—C10—C11 | 121.59 (19) |
C4—Fe1—C2—C1 | 81.48 (12) | C6—Fe1—C10—C11 | −119.85 (19) |
C4—C5—C1—C2 | −0.2 (2) | C7—Fe1—C10—C11 | −157.23 (17) |
Fe1—C5—C1—C2 | 59.43 (13) | C5—Fe1—C10—C11 | −34.05 (18) |
C4—C5—C1—Fe1 | −59.63 (13) | C3—Fe1—C10—C11 | 85.6 (3) |
C3—C2—C1—C5 | 0.2 (2) | C4—Fe1—C10—C11 | −69.5 (2) |
Fe1—C2—C1—C5 | −59.62 (12) | C21—N1—C11—C10 | 82.3 (2) |
C3—C2—C1—Fe1 | 59.82 (13) | N2—N1—C11—C10 | −103.92 (15) |
C8—Fe1—C1—C5 | 164.87 (15) | C21—N1—C11—C12 | −157.18 (16) |
C2—Fe1—C1—C5 | 118.94 (16) | N2—N1—C11—C12 | 16.65 (16) |
C9—Fe1—C1—C5 | −159.12 (11) | C9—C10—C11—N1 | −104.11 (18) |
C6—Fe1—C1—C5 | −74.48 (14) | C6—C10—C11—N1 | 72.8 (2) |
C7—Fe1—C1—C5 | −38.9 (4) | Fe1—C10—C11—N1 | 163.79 (12) |
C10—Fe1—C1—C5 | −115.62 (11) | C9—C10—C11—C12 | 144.09 (17) |
C3—Fe1—C1—C5 | 81.13 (12) | C6—C10—C11—C12 | −39.0 (2) |
C4—Fe1—C1—C5 | 37.62 (11) | Fe1—C10—C11—C12 | 52.0 (2) |
C8—Fe1—C1—C2 | 45.9 (2) | N1—C11—C12—C13 | −15.48 (15) |
C9—Fe1—C1—C2 | 81.94 (13) | C10—C11—C12—C13 | 101.72 (15) |
C6—Fe1—C1—C2 | 166.58 (11) | N1—N2—C13—C14 | 179.95 (14) |
C7—Fe1—C1—C2 | −157.8 (3) | N1—N2—C13—C12 | −1.10 (19) |
C5—Fe1—C1—C2 | −118.94 (16) | C11—C12—C13—N2 | 11.39 (18) |
C10—Fe1—C1—C2 | 125.44 (12) | C11—C12—C13—C14 | −169.70 (15) |
C3—Fe1—C1—C2 | −37.81 (12) | N2—C13—C14—C15 | 172.56 (16) |
C4—Fe1—C1—C2 | −81.33 (12) | C12—C13—C14—C15 | −6.3 (2) |
C8—Fe1—C6—C7 | −37.65 (12) | N2—C13—C14—C19 | −8.2 (2) |
C2—Fe1—C6—C7 | −152.3 (3) | C12—C13—C14—C19 | 172.93 (16) |
C1—Fe1—C6—C7 | 168.21 (12) | C19—C14—C15—C16 | −0.1 (3) |
C9—Fe1—C6—C7 | −81.56 (12) | C13—C14—C15—C16 | 179.08 (16) |
C5—Fe1—C6—C7 | 126.32 (12) | C14—C15—C16—C17 | 0.1 (3) |
C10—Fe1—C6—C7 | −119.67 (16) | C15—C16—C17—C18 | −0.2 (3) |
C3—Fe1—C6—C7 | 45.3 (2) | C15—C16—C17—C20 | −179.84 (18) |
C4—Fe1—C6—C7 | 82.72 (13) | C16—C17—C18—C19 | 0.3 (3) |
C8—Fe1—C6—C10 | 82.03 (11) | C20—C17—C18—C19 | −179.98 (18) |
C2—Fe1—C6—C10 | −32.7 (4) | C17—C18—C19—C14 | −0.4 (3) |
C1—Fe1—C6—C10 | −72.12 (13) | C15—C14—C19—C18 | 0.3 (3) |
C9—Fe1—C6—C10 | 38.12 (10) | C13—C14—C19—C18 | −178.90 (16) |
C7—Fe1—C6—C10 | 119.67 (16) | N2—N1—C21—S2 | −174.50 (11) |
C5—Fe1—C6—C10 | −114.01 (11) | C11—N1—C21—S2 | −1.1 (2) |
C3—Fe1—C6—C10 | 164.99 (15) | N2—N1—C21—S1 | 5.40 (19) |
C4—Fe1—C6—C10 | −157.61 (10) | C11—N1—C21—S1 | 178.78 (12) |
C10—C6—C7—C8 | 0.2 (2) | C22—S1—C21—N1 | 175.13 (13) |
Fe1—C6—C7—C8 | 59.27 (13) | C22—S1—C21—S2 | −4.97 (14) |
C10—C6—C7—Fe1 | −59.11 (12) | C21—S1—C22—C23 | −175.12 (14) |
C2—Fe1—C7—C8 | 47.6 (2) | S1—C22—C23—C24 | 102.92 (18) |
C1—Fe1—C7—C8 | −163.0 (3) | S1—C22—C23—C28 | −78.0 (2) |
C9—Fe1—C7—C8 | −37.54 (11) | C24—C23—C28—C27 | 2.2 (3) |
C6—Fe1—C7—C8 | −119.15 (16) | C22—C23—C28—C27 | −176.87 (18) |
C5—Fe1—C7—C8 | 165.48 (11) | C23—C28—C27—C26 | −1.2 (3) |
C10—Fe1—C7—C8 | −81.54 (12) | C28—C27—C26—C25 | −0.7 (3) |
C3—Fe1—C7—C8 | 82.39 (13) | C27—C26—C25—C24 | 1.7 (3) |
C4—Fe1—C7—C8 | 125.13 (12) | C28—C23—C24—C25 | −1.2 (3) |
C8—Fe1—C7—C6 | 119.15 (16) | C22—C23—C24—C25 | 177.82 (18) |
C2—Fe1—C7—C6 | 166.76 (15) | C26—C25—C24—C23 | −0.7 (3) |
Experimental details
Crystal data | |
Chemical formula | [Fe(C5H5)(C23H21N2S2)] |
Mr | 510.50 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 9.178 (1), 10.468 (2), 13.216 (2) |
α, β, γ (°) | 99.37 (1), 101.55 (2), 96.12 (1) |
V (Å3) | 1214.6 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.81 |
Crystal size (mm) | 0.33 × 0.31 × 0.28 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.776, 0.805 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10742, 5528, 5035 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.653 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.088, 0.99 |
No. of reflections | 5528 |
No. of parameters | 299 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.44, −0.22 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Bruker, 2002).
Acknowledgements
The authors thank the Natural Science Foundation of Yangzhou University (No. 2006XJJ03) for financial support of this work.
References
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Pyrazoline derivatives are an important class of conjugated fluorescent dyes emitting blue fluorescence and have been extensively applied in the industry due to the high fluorescence quantum yield (Wilkinson et al., 1990; Rivett et al., 1979). For example, pyrazolines have been widely used as optical brightening agents for textiles, paper and fabrics and as a hole-conveying medium in photoconductive materials (Sun et al., 2004; Huang & Katzenellenbogen, 2000; Wiley et al., 1958). We found that ferrocene derivatives have good properties of fluorescence and coordination chemistry with many metal ions (Huang et al., 1998; Shi et al., 2004). Continuing our research (Liu et al., 2007) we report the synthesis and structure of the title compound, (I).
In the structure of (I), the substituted ring (Cps) and unsubstituted ring (Cp) of the ferrocenyl moiety are slightly deprived from eclipsed form, with the five pseudo-torsion angles in the range 10.5 (2) — 10.9 (3)°. The distances from central Fe(II) ion to Cps center [Cg(1)] and to Cp center [Cg(2)] are 1.651 (3) Å and 1.656 (2) Å, respectively. The angle Cg(1)–Fe–Cg(2) is 177.9 (3)° and the central Fe(II) ion is located almost in the middle of the two cyclopentadiene rings which are not parallel because their dihedral angle is 2.3 (4)° (Fig. 1).
In the pyrazolinyl ring, the C=N and C–N bond lengths are in agreement with those found in similar structures (Fahrni et al., 2003). However, the N–N bond length is longer than those found in the above-cited structures. But the bond distance of C21–N1 is shorter than a C–N single bond and slight longer than a C=N double bond. It might contribute to unclassical sp2-hybrid N1 atom which is evident from the sum of the three angles around the N1 atom being 360° (Table 1) and that atoms C21, N1, N2 and C13 are co-planar. Furthemore, atoms S2, C21, N1, N2, C13 along with adjacent phenyl ring result in a large cojugated system.
In its packing diagram, the molecules of (I) are linked into two invers chains via C— H···S intermolecular hydrogen-bonds with C···S distance 3.583 (3) Å and C26—H26···S2 angle 142°, along the b axis (Fig. 2, Table 2).