1-[(Ferrocen-1-yl)meth­yl]-3-(naphthalen-1-yl)thio­urea

Li, X.; Liu, W.

doi:10.1107/S1600536811046629

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1744

https://doi.org/10.1107/S1600536811046629

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1-[(Ferrocen-1-yl)methyl]-3-(naphthalen-1-yl)thiourea

Xia Li ^a ^* and Wei Liu ^a

^aDepartment of Chemistry and Chemical Engineering, Henan University of Urban Construction, Pingdingshan, Henan 467044, People's Republic of China
^*Correspondence e-mail: lixia@hncj.edu.cn

(Received 10 October 2011; accepted 5 November 2011; online 12 November 2011)

In the title compound, [Fe(C₅H₅)(C₁₇H₁₅N₂S)], the cyclopentadienyl (Cp) rings are almost parallel and essentially eclipsed, with a dihedral angle between the Cp ring planes of 0.807 (11)°. The Fe atom is slightly closer to the substituted cyclopentadienyl ring, with an Fe–centroid distance of 1.6510 (8) Å, compared with 1.6597 (8) Å for the unsubstituted ring. The bridging unit between the substituted Cp ring and the naphthyl ring system is planar within 0.0174 Å and makes dihedral angles of 59.032 (10) and 66.02 (2)°, respectively, with these two rings. The angle between the substituted Cp ring and the naphthyl ring system is 72.094 (18)°. The H atoms of the NH groups of the thiourea moiety are positioned anti with respect to each other. In the crystal, molecules form centrosymmetric dimers via pairs of N—H⋯S hydrogen bonds.

Related literature

For applications of thiourea in the field of medicine, see: Di Grandi et al. (2004 ); Suh et al. (2005 ); Kaymakcioglu et al. (2005 ); Han et al. (2006 ), in bioorganic chemistry, see: Rostom (2006 ) and in supramolecular chemistry, see: Henderson et al. (2001 ); Heck & Marsura (2003 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₇H₁₅N₂S)]
M_r = 400.31
Triclinic, $[P \overline 1]$
a = 7.958 (3) Å
b = 10.890 (5) Å
c = 12.357 (5) Å
α = 66.886 (6)°
β = 78.637 (8)°
γ = 73.306 (8)°
V = 939.1 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.92 mm⁻¹
T = 296 K
0.39 × 0.24 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.755, T_max = 0.867
5178 measured reflections
3645 independent reflections
2741 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.105
S = 1.04
3645 reflections
241 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯S1ⁱ	0.90 (3)	2.45 (3)	3.326 (3)	167 (2)
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811046629/fj2464sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046629/fj2464Isup2.hkl

checkCIF report

Comment top

Thiourea and its derivatives have attracted great attention because of their potential applications in the field of medicine (Di Grandi et al., 2004; Suh et al., 2005; Kaymakcioglu et al., 2005; Han et al., 2006), bioorganic (Rostom et al., 2006) and supramolecular chemistry (Henderson et al., 2001; Heck et al., 2003). Detailed information on their molecular and crystal structures is necessary to understand their biologic activity and coordination possibility. Here we want to report the crystal structure of a new ferrocene-containing thiourea, 1-((ferroecen-1-yl)methyl)-3-(naphthalen-1-yl)thiourea.

The molecular structure of the title compound is composed of a (ferroecen-1-yl)methyl group and a naphthalen group joined by an organic thiourea spacer. The Fe—C bond distances within the ferrocene group are in the range of 2.043 (3)–2.048 (3) Å for the substituted cyclopentadienyl (Cp) ring [C1—C5] and 2.033 (3)–2.048 (3) Å for the unsubstituted Cp ring [C6—C10]. The Cp rings are almost parallel and are essentially eclipsed, and the dihedral angle between the Cp ring planes is 0.807 (11) °. The Fe atom is slightly closer to the substituted cyclopentadienyl ring, with a Fe-centroid distance of 1.6510 (8) Å, compared with 1.6597 (8) Å for the unsubstituted ring. The bridging unit between the substituted Cp ring and naphthyl rings is planar within 0.0174 Å and makes dihedral angles of 59.032 (10) ° and 66.019 (21) °, respectively, with these two rings, while the angle between the substituted Cp ring and naphthyl rings is 72.094 (18) °. The H atoms of the NH groups of thiourea are positioned anti to each other. In the crystal, the molecules form centrosymmetric dimers via intermolecular N—H···S hydrogen bonds.

Related literature top

For applications of thiourea in the field of medicine, see: Di Grandi et al. (2004); Suh et al. (2005); Kaymakcioglu et al. (2005); Han et al. (2006), in bioorganic chemistry, see: Rostom (2006) and in supramolecular chemistry, see: Henderson et al. (2001); Heck & Marsura (2003).

Experimental top

To a solution of (ferrocene-1-yl)methanamine (1.075 g, 5 mmol) in MeOH (30 ml), 1-naphthyl isothiocyanate (0.925 g, 5 mmol) was added. The reaction mixture was stirred at room temperature for 12 h. The resulting solution was concentrated to about 10 ml and then cooled at ice-bath. The yellow precipitate was collected by filtration and washed with Ether several times. The crude product was purified by recrystallization from CH₂Cl₂ / MeOH to give 1-((ferroecen-1-yl)methyl)-3-(naphthalen-1-yl)thiourea as yellow block crystals.

Structure description top

For applications of thiourea in the field of medicine, see: Di Grandi et al. (2004); Suh et al. (2005); Kaymakcioglu et al. (2005); Han et al. (2006), in bioorganic chemistry, see: Rostom (2006) and in supramolecular chemistry, see: Henderson et al. (2001); Heck & Marsura (2003).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atomic numbering and 30% probability displacement ellipsoids.

1-[(Ferrocen-1-yl)methyl]-3-(naphthalen-1-yl)thiourea top

Crystal data top

[Fe(C₅H₅)(C₁₇H₁₅N₂S)]	V = 939.1 (7) Å³
M_r = 400.31	Z = 2
Triclinic, P1	F(000) = 416
Hall symbol: -P 1	D_x = 1.416 Mg m⁻³
a = 7.958 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.890 (5) Å	θ = 1.8–28.2°
c = 12.357 (5) Å	µ = 0.92 mm⁻¹
α = 66.886 (6)°	T = 296 K
β = 78.637 (8)°	Block, orange
γ = 73.306 (8)°	0.39 × 0.24 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3645 independent reflections
Radiation source: fine-focus sealed tube	2741 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
phi and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −9→9
T_min = 0.755, T_max = 0.867	k = −9→13
5178 measured reflections	l = −14→15

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0467P)² + 0.1883P] where P = (F_o² + 2F_c²)/3
3645 reflections	(Δ/σ)_max < 0.001
241 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₇H₁₅N₂S)]	γ = 73.306 (8)°
M_r = 400.31	V = 939.1 (7) Å³
Triclinic, P1	Z = 2
a = 7.958 (3) Å	Mo Kα radiation
b = 10.890 (5) Å	µ = 0.92 mm⁻¹
c = 12.357 (5) Å	T = 296 K
α = 66.886 (6)°	0.39 × 0.24 × 0.16 mm
β = 78.637 (8)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3645 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	2741 reflections with I > 2σ(I)
T_min = 0.755, T_max = 0.867	R_int = 0.018
5178 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.35 e Å⁻³
3645 reflections	Δρ_min = −0.32 e Å⁻³
241 parameters

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.

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	U_iso*/U_eq
Fe1	0.28952 (5)	0.28154 (4)	0.44361 (3)	0.04797 (15)
S1	0.81798 (10)	0.59967 (7)	0.11000 (7)	0.0553 (2)
N1	0.6093 (3)	0.4257 (2)	0.2183 (2)	0.0559 (7)
N2	0.8196 (3)	0.3739 (2)	0.0768 (2)	0.0513 (6)
C1	0.4345 (4)	0.4236 (3)	0.4046 (2)	0.0500 (7)
C2	0.2684 (4)	0.4629 (3)	0.4647 (3)	0.0558 (7)
H2	0.1844	0.5443	0.4358	0.067*
C3	0.2523 (5)	0.3575 (3)	0.5759 (3)	0.0645 (8)
H3	0.1556	0.3570	0.6322	0.077*
C4	0.4083 (5)	0.2533 (4)	0.5866 (3)	0.0689 (9)
H4	0.4326	0.1721	0.6512	0.083*
C5	0.5222 (4)	0.2936 (3)	0.4814 (3)	0.0602 (8)
H5	0.6343	0.2438	0.4655	0.072*
C6	0.2304 (5)	0.2825 (4)	0.2899 (3)	0.0716 (9)
H6	0.2558	0.3436	0.2146	0.086*
C7	0.0759 (4)	0.3020 (4)	0.3636 (3)	0.0747 (10)
H7	−0.0190	0.3778	0.3458	0.090*
C8	0.0883 (6)	0.1880 (5)	0.4690 (4)	0.0851 (12)
H8	0.0040	0.1739	0.5338	0.102*
C9	0.2543 (6)	0.0979 (4)	0.4579 (4)	0.0871 (12)
H9	0.2987	0.0137	0.5147	0.104*
C10	0.3395 (5)	0.1579 (4)	0.3468 (4)	0.0780 (10)
H10	0.4501	0.1204	0.3166	0.094*
C11	0.5046 (4)	0.5097 (3)	0.2864 (3)	0.0634 (8)
H11A	0.4071	0.5746	0.2429	0.076*
H11B	0.5770	0.5615	0.2968	0.076*
C12	0.7436 (3)	0.4578 (3)	0.1373 (2)	0.0433 (6)
C13	0.7688 (3)	0.2533 (3)	0.0865 (2)	0.0445 (6)
C14	0.6119 (4)	0.2638 (3)	0.0504 (3)	0.0550 (7)
H14	0.5362	0.3497	0.0215	0.066*
C15	0.5630 (4)	0.1469 (4)	0.0563 (3)	0.0646 (9)
H15	0.4541	0.1553	0.0340	0.078*
C16	0.6750 (4)	0.0220 (4)	0.0946 (3)	0.0623 (8)
H16	0.6429	−0.0546	0.0968	0.075*
C17	0.8410 (4)	0.0057 (3)	0.1316 (2)	0.0492 (7)
C18	0.9628 (5)	−0.1220 (3)	0.1691 (3)	0.0666 (9)
H18	0.9360	−0.1994	0.1686	0.080*
C19	1.1183 (5)	−0.1343 (3)	0.2060 (3)	0.0779 (10)
H19	1.1966	−0.2198	0.2303	0.093*
C20	1.1618 (4)	−0.0202 (4)	0.2079 (3)	0.0700 (9)
H20	1.2678	−0.0305	0.2351	0.084*
C21	1.0513 (4)	0.1059 (3)	0.1705 (3)	0.0562 (7)
H21	1.0828	0.1814	0.1714	0.067*
C22	0.8878 (3)	0.1236 (3)	0.1299 (2)	0.0426 (6)
H1A	0.577 (4)	0.357 (3)	0.230 (2)	0.051*
H2A	0.921 (4)	0.389 (3)	0.033 (2)	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0496 (2)	0.0505 (3)	0.0520 (3)	−0.01930 (18)	−0.00125 (18)	−0.02317 (19)
S1	0.0595 (4)	0.0442 (4)	0.0712 (5)	−0.0267 (3)	0.0129 (4)	−0.0287 (4)
N1	0.0636 (15)	0.0482 (14)	0.0679 (16)	−0.0311 (12)	0.0227 (12)	−0.0341 (13)
N2	0.0472 (13)	0.0477 (14)	0.0668 (16)	−0.0240 (11)	0.0165 (11)	−0.0298 (12)
C1	0.0560 (16)	0.0482 (16)	0.0578 (17)	−0.0207 (13)	0.0047 (13)	−0.0301 (14)
C2	0.0613 (18)	0.0536 (17)	0.0584 (18)	−0.0166 (14)	0.0067 (14)	−0.0298 (15)
C3	0.074 (2)	0.076 (2)	0.0555 (19)	−0.0343 (18)	0.0120 (16)	−0.0334 (17)
C4	0.091 (3)	0.072 (2)	0.0521 (19)	−0.0320 (19)	−0.0182 (18)	−0.0162 (17)
C5	0.0537 (17)	0.063 (2)	0.078 (2)	−0.0135 (14)	−0.0135 (16)	−0.0362 (17)
C6	0.083 (2)	0.090 (3)	0.063 (2)	−0.039 (2)	−0.0065 (19)	−0.036 (2)
C7	0.058 (2)	0.089 (3)	0.096 (3)	−0.0177 (18)	−0.0148 (19)	−0.049 (2)
C8	0.087 (3)	0.119 (3)	0.081 (3)	−0.069 (3)	0.015 (2)	−0.048 (3)
C9	0.113 (3)	0.055 (2)	0.107 (3)	−0.035 (2)	−0.040 (3)	−0.019 (2)
C10	0.076 (2)	0.086 (3)	0.104 (3)	−0.026 (2)	−0.004 (2)	−0.064 (3)
C11	0.076 (2)	0.0511 (18)	0.070 (2)	−0.0252 (15)	0.0233 (16)	−0.0351 (16)
C12	0.0441 (14)	0.0395 (14)	0.0496 (15)	−0.0149 (11)	−0.0004 (12)	−0.0178 (12)
C13	0.0486 (15)	0.0469 (15)	0.0494 (15)	−0.0234 (12)	0.0082 (12)	−0.0267 (13)
C14	0.0532 (17)	0.0577 (18)	0.0621 (18)	−0.0174 (14)	−0.0050 (14)	−0.0269 (15)
C15	0.0611 (19)	0.088 (3)	0.068 (2)	−0.0358 (18)	0.0002 (16)	−0.0422 (19)
C16	0.079 (2)	0.072 (2)	0.0627 (19)	−0.0482 (18)	0.0104 (16)	−0.0378 (17)
C17	0.0658 (18)	0.0450 (16)	0.0458 (15)	−0.0278 (14)	0.0115 (13)	−0.0232 (13)
C18	0.097 (3)	0.0452 (18)	0.0589 (19)	−0.0302 (17)	0.0167 (18)	−0.0212 (15)
C19	0.090 (3)	0.0484 (19)	0.074 (2)	−0.0020 (18)	0.003 (2)	−0.0143 (17)
C20	0.0595 (19)	0.067 (2)	0.075 (2)	−0.0083 (16)	−0.0095 (17)	−0.0198 (18)
C21	0.0570 (17)	0.0568 (18)	0.0623 (18)	−0.0237 (14)	0.0004 (14)	−0.0247 (15)
C22	0.0479 (15)	0.0470 (15)	0.0425 (14)	−0.0238 (12)	0.0093 (12)	−0.0233 (12)

Geometric parameters (Å, º) top

Fe1—C9	2.033 (3)	C6—H6	0.9300
Fe1—C6	2.040 (3)	C7—C8	1.400 (5)
Fe1—C10	2.042 (3)	C7—H7	0.9300
Fe1—C4	2.043 (3)	C8—C9	1.420 (6)
Fe1—C3	2.043 (3)	C8—H8	0.9300
Fe1—C1	2.044 (3)	C9—C10	1.398 (5)
Fe1—C7	2.046 (3)	C9—H9	0.9300
Fe1—C8	2.047 (3)	C10—H10	0.9300
Fe1—C5	2.047 (3)	C11—H11A	0.9700
Fe1—C2	2.048 (3)	C11—H11B	0.9700
S1—C12	1.699 (3)	C13—C14	1.366 (4)
N1—C12	1.336 (3)	C13—C22	1.420 (4)
N1—C11	1.458 (3)	C14—C15	1.407 (4)
N1—H1A	0.81 (3)	C14—H14	0.9300
N2—C12	1.342 (3)	C15—C16	1.354 (5)
N2—C13	1.437 (3)	C15—H15	0.9300
N2—H2A	0.90 (3)	C16—C17	1.423 (4)
C1—C2	1.421 (4)	C16—H16	0.9300
C1—C5	1.425 (4)	C17—C18	1.409 (4)
C1—C11	1.493 (4)	C17—C22	1.428 (3)
C2—C3	1.414 (4)	C18—C19	1.355 (5)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.409 (5)	C19—C20	1.393 (5)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.421 (4)	C20—C21	1.357 (4)
C4—H4	0.9300	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.421 (4)
C6—C10	1.380 (5)	C21—H21	0.9300
C6—C7	1.396 (5)

C9—Fe1—C6	66.95 (16)	C4—C5—C1	108.0 (3)
C9—Fe1—C10	40.13 (16)	C4—C5—Fe1	69.49 (17)
C6—Fe1—C10	39.51 (14)	C1—C5—Fe1	69.49 (16)
C9—Fe1—C4	108.65 (15)	C4—C5—H5	126.0
C6—Fe1—C4	165.75 (15)	C1—C5—H5	126.0
C10—Fe1—C4	128.50 (16)	Fe1—C5—H5	126.6
C9—Fe1—C3	127.08 (16)	C10—C6—C7	108.9 (3)
C6—Fe1—C3	153.19 (15)	C10—C6—Fe1	70.3 (2)
C10—Fe1—C3	165.09 (16)	C7—C6—Fe1	70.26 (19)
C4—Fe1—C3	40.33 (13)	C10—C6—H6	125.6
C9—Fe1—C1	154.07 (16)	C7—C6—H6	125.6
C6—Fe1—C1	109.02 (13)	Fe1—C6—H6	125.4
C10—Fe1—C1	120.19 (14)	C6—C7—C8	108.3 (4)
C4—Fe1—C1	68.58 (12)	C6—C7—Fe1	69.80 (19)
C3—Fe1—C1	68.53 (12)	C8—C7—Fe1	70.0 (2)
C9—Fe1—C7	67.36 (16)	C6—C7—H7	125.8
C6—Fe1—C7	39.94 (13)	C8—C7—H7	125.8
C10—Fe1—C7	67.04 (15)	Fe1—C7—H7	125.9
C4—Fe1—C7	152.63 (15)	C7—C8—C9	106.7 (3)
C3—Fe1—C7	118.87 (14)	C7—C8—Fe1	69.98 (19)
C1—Fe1—C7	127.19 (14)	C9—C8—Fe1	69.1 (2)
C9—Fe1—C8	40.73 (16)	C7—C8—H8	126.6
C6—Fe1—C8	67.34 (15)	C9—C8—H8	126.6
C10—Fe1—C8	67.84 (15)	Fe1—C8—H8	125.8
C4—Fe1—C8	118.94 (15)	C10—C9—C8	108.1 (4)
C3—Fe1—C8	107.16 (14)	C10—C9—Fe1	70.29 (19)
C1—Fe1—C8	163.82 (16)	C8—C9—Fe1	70.2 (2)
C7—Fe1—C8	39.99 (15)	C10—C9—H9	125.9
C9—Fe1—C5	120.16 (15)	C8—C9—H9	125.9
C6—Fe1—C5	128.50 (13)	Fe1—C9—H9	125.2
C10—Fe1—C5	109.68 (14)	C6—C10—C9	108.0 (4)
C4—Fe1—C5	40.66 (13)	C6—C10—Fe1	70.17 (19)
C3—Fe1—C5	68.15 (13)	C9—C10—Fe1	69.6 (2)
C1—Fe1—C5	40.76 (12)	C6—C10—H10	126.0
C7—Fe1—C5	165.29 (15)	C9—C10—H10	126.0
C8—Fe1—C5	153.72 (17)	Fe1—C10—H10	125.8
C9—Fe1—C2	164.22 (17)	N1—C11—C1	111.5 (2)
C6—Fe1—C2	120.10 (14)	N1—C11—H11A	109.3
C10—Fe1—C2	153.81 (15)	C1—C11—H11A	109.3
C4—Fe1—C2	67.90 (13)	N1—C11—H11B	109.3
C3—Fe1—C2	40.44 (12)	C1—C11—H11B	109.3
C1—Fe1—C2	40.65 (11)	H11A—C11—H11B	108.0
C7—Fe1—C2	108.15 (14)	N1—C12—N2	117.7 (2)
C8—Fe1—C2	126.17 (15)	N1—C12—S1	122.01 (19)
C5—Fe1—C2	68.03 (12)	N2—C12—S1	120.24 (19)
C12—N1—C11	125.0 (2)	C14—C13—C22	120.7 (2)
C12—N1—H1A	120 (2)	C14—C13—N2	120.6 (3)
C11—N1—H1A	115 (2)	C22—C13—N2	118.7 (2)
C12—N2—C13	127.0 (2)	C13—C14—C15	121.1 (3)
C12—N2—H2A	115.8 (17)	C13—C14—H14	119.4
C13—N2—H2A	116.7 (17)	C15—C14—H14	119.4
C2—C1—C5	107.2 (3)	C16—C15—C14	119.8 (3)
C2—C1—C11	125.1 (3)	C16—C15—H15	120.1
C5—C1—C11	127.6 (3)	C14—C15—H15	120.1
C2—C1—Fe1	69.82 (16)	C15—C16—C17	121.3 (3)
C5—C1—Fe1	69.75 (16)	C15—C16—H16	119.4
C11—C1—Fe1	128.7 (2)	C17—C16—H16	119.4
C3—C2—C1	108.5 (3)	C18—C17—C16	122.9 (3)
C3—C2—Fe1	69.61 (17)	C18—C17—C22	118.2 (3)
C1—C2—Fe1	69.53 (15)	C16—C17—C22	119.0 (3)
C3—C2—H2	125.7	C19—C18—C17	121.4 (3)
C1—C2—H2	125.7	C19—C18—H18	119.3
Fe1—C2—H2	126.7	C17—C18—H18	119.3
C4—C3—C2	108.1 (3)	C18—C19—C20	120.5 (3)
C4—C3—Fe1	69.82 (18)	C18—C19—H19	119.7
C2—C3—Fe1	69.96 (16)	C20—C19—H19	119.7
C4—C3—H3	126.0	C21—C20—C19	120.7 (3)
C2—C3—H3	126.0	C21—C20—H20	119.6
Fe1—C3—H3	125.8	C19—C20—H20	119.6
C3—C4—C5	108.2 (3)	C20—C21—C22	120.5 (3)
C3—C4—Fe1	69.85 (18)	C20—C21—H21	119.7
C5—C4—Fe1	69.85 (17)	C22—C21—H21	119.7
C3—C4—H4	125.9	C13—C22—C21	123.2 (2)
C5—C4—H4	125.9	C13—C22—C17	118.1 (2)
Fe1—C4—H4	126.0	C21—C22—C17	118.6 (3)

C9—Fe1—C1—C2	−169.4 (3)	C10—Fe1—C6—C7	119.6 (3)
C6—Fe1—C1—C2	114.4 (2)	C4—Fe1—C6—C7	156.5 (5)
C10—Fe1—C1—C2	156.4 (2)	C3—Fe1—C6—C7	−45.9 (4)
C4—Fe1—C1—C2	−80.6 (2)	C1—Fe1—C6—C7	−125.7 (2)
C3—Fe1—C1—C2	−37.12 (19)	C8—Fe1—C6—C7	37.4 (2)
C7—Fe1—C1—C2	73.5 (2)	C5—Fe1—C6—C7	−167.2 (2)
C8—Fe1—C1—C2	40.3 (5)	C2—Fe1—C6—C7	−82.4 (2)
C5—Fe1—C1—C2	−118.1 (2)	C10—C6—C7—C8	0.3 (4)
C9—Fe1—C1—C5	−51.2 (4)	Fe1—C6—C7—C8	−59.7 (2)
C6—Fe1—C1—C5	−127.48 (19)	C10—C6—C7—Fe1	59.9 (2)
C10—Fe1—C1—C5	−85.5 (2)	C9—Fe1—C7—C6	−80.6 (3)
C4—Fe1—C1—C5	37.54 (18)	C10—Fe1—C7—C6	−36.9 (2)
C3—Fe1—C1—C5	81.0 (2)	C4—Fe1—C7—C6	−167.7 (3)
C7—Fe1—C1—C5	−168.33 (19)	C3—Fe1—C7—C6	158.3 (2)
C8—Fe1—C1—C5	158.4 (4)	C1—Fe1—C7—C6	74.4 (3)
C2—Fe1—C1—C5	118.1 (2)	C8—Fe1—C7—C6	−119.3 (3)
C9—Fe1—C1—C11	71.3 (4)	C5—Fe1—C7—C6	43.1 (6)
C6—Fe1—C1—C11	−4.9 (3)	C2—Fe1—C7—C6	115.5 (2)
C10—Fe1—C1—C11	37.0 (3)	C9—Fe1—C7—C8	38.7 (2)
C4—Fe1—C1—C11	160.1 (3)	C6—Fe1—C7—C8	119.3 (3)
C3—Fe1—C1—C11	−156.4 (3)	C10—Fe1—C7—C8	82.4 (3)
C7—Fe1—C1—C11	−45.8 (3)	C4—Fe1—C7—C8	−48.3 (4)
C8—Fe1—C1—C11	−79.0 (5)	C3—Fe1—C7—C8	−82.4 (3)
C5—Fe1—C1—C11	122.5 (3)	C1—Fe1—C7—C8	−166.3 (2)
C2—Fe1—C1—C11	−119.3 (3)	C5—Fe1—C7—C8	162.4 (5)
C5—C1—C2—C3	−1.2 (3)	C2—Fe1—C7—C8	−125.1 (2)
C11—C1—C2—C3	−177.4 (3)	C6—C7—C8—C9	−0.1 (4)
Fe1—C1—C2—C3	58.9 (2)	Fe1—C7—C8—C9	−59.6 (2)
C5—C1—C2—Fe1	−60.01 (18)	C6—C7—C8—Fe1	59.5 (2)
C11—C1—C2—Fe1	123.7 (3)	C9—Fe1—C8—C7	−117.8 (3)
C9—Fe1—C2—C3	42.7 (6)	C6—Fe1—C8—C7	−37.3 (2)
C6—Fe1—C2—C3	155.5 (2)	C10—Fe1—C8—C7	−80.2 (2)
C10—Fe1—C2—C3	−171.8 (3)	C4—Fe1—C8—C7	156.9 (2)
C4—Fe1—C2—C3	−37.6 (2)	C3—Fe1—C8—C7	114.7 (2)
C1—Fe1—C2—C3	−120.0 (3)	C1—Fe1—C8—C7	42.8 (6)
C7—Fe1—C2—C3	113.5 (2)	C5—Fe1—C8—C7	−170.0 (3)
C8—Fe1—C2—C3	72.9 (3)	C2—Fe1—C8—C7	74.3 (3)
C5—Fe1—C2—C3	−81.6 (2)	C6—Fe1—C8—C9	80.5 (3)
C9—Fe1—C2—C1	162.8 (5)	C10—Fe1—C8—C9	37.6 (2)
C6—Fe1—C2—C1	−84.4 (2)	C4—Fe1—C8—C9	−85.3 (3)
C10—Fe1—C2—C1	−51.8 (4)	C3—Fe1—C8—C9	−127.5 (2)
C4—Fe1—C2—C1	82.4 (2)	C1—Fe1—C8—C9	160.6 (4)
C3—Fe1—C2—C1	120.0 (3)	C7—Fe1—C8—C9	117.8 (3)
C7—Fe1—C2—C1	−126.5 (2)	C5—Fe1—C8—C9	−52.2 (4)
C8—Fe1—C2—C1	−167.1 (2)	C2—Fe1—C8—C9	−167.9 (2)
C5—Fe1—C2—C1	38.38 (18)	C7—C8—C9—C10	−0.1 (4)
C1—C2—C3—C4	0.8 (3)	Fe1—C8—C9—C10	−60.3 (2)
Fe1—C2—C3—C4	59.6 (2)	C7—C8—C9—Fe1	60.2 (2)
C1—C2—C3—Fe1	−58.80 (19)	C6—Fe1—C9—C10	37.2 (2)
C9—Fe1—C3—C4	74.3 (3)	C4—Fe1—C9—C10	−128.2 (2)
C6—Fe1—C3—C4	−171.7 (3)	C3—Fe1—C9—C10	−169.4 (2)
C10—Fe1—C3—C4	46.7 (6)	C1—Fe1—C9—C10	−49.0 (4)
C1—Fe1—C3—C4	−81.8 (2)	C7—Fe1—C9—C10	80.7 (2)
C7—Fe1—C3—C4	156.6 (2)	C8—Fe1—C9—C10	118.7 (3)
C8—Fe1—C3—C4	114.8 (2)	C5—Fe1—C9—C10	−85.1 (3)
C5—Fe1—C3—C4	−37.76 (19)	C2—Fe1—C9—C10	157.2 (5)
C2—Fe1—C3—C4	−119.1 (3)	C6—Fe1—C9—C8	−81.5 (3)
C9—Fe1—C3—C2	−166.6 (2)	C10—Fe1—C9—C8	−118.7 (3)
C6—Fe1—C3—C2	−52.6 (4)	C4—Fe1—C9—C8	113.0 (3)
C10—Fe1—C3—C2	165.8 (5)	C3—Fe1—C9—C8	71.9 (3)
C4—Fe1—C3—C2	119.1 (3)	C1—Fe1—C9—C8	−167.8 (3)
C1—Fe1—C3—C2	37.31 (18)	C7—Fe1—C9—C8	−38.0 (2)
C7—Fe1—C3—C2	−84.3 (2)	C5—Fe1—C9—C8	156.1 (2)
C8—Fe1—C3—C2	−126.2 (2)	C2—Fe1—C9—C8	38.4 (6)
C5—Fe1—C3—C2	81.3 (2)	C7—C6—C10—C9	−0.4 (4)
C2—C3—C4—C5	−0.2 (3)	Fe1—C6—C10—C9	59.6 (2)
Fe1—C3—C4—C5	59.5 (2)	C7—C6—C10—Fe1	−59.9 (2)
C2—C3—C4—Fe1	−59.7 (2)	C8—C9—C10—C6	0.3 (4)
C9—Fe1—C4—C3	−125.8 (2)	Fe1—C9—C10—C6	−59.9 (2)
C6—Fe1—C4—C3	164.6 (5)	C8—C9—C10—Fe1	60.2 (2)
C10—Fe1—C4—C3	−166.1 (2)	C9—Fe1—C10—C6	118.9 (3)
C1—Fe1—C4—C3	81.6 (2)	C4—Fe1—C10—C6	−169.1 (2)
C7—Fe1—C4—C3	−49.2 (4)	C3—Fe1—C10—C6	153.9 (5)
C8—Fe1—C4—C3	−82.5 (2)	C1—Fe1—C10—C6	−83.5 (2)
C5—Fe1—C4—C3	119.3 (3)	C7—Fe1—C10—C6	37.3 (2)
C2—Fe1—C4—C3	37.71 (18)	C8—Fe1—C10—C6	80.8 (2)
C9—Fe1—C4—C5	114.9 (2)	C5—Fe1—C10—C6	−127.3 (2)
C6—Fe1—C4—C5	45.3 (6)	C2—Fe1—C10—C6	−47.2 (4)
C10—Fe1—C4—C5	74.6 (2)	C6—Fe1—C10—C9	−118.9 (3)
C3—Fe1—C4—C5	−119.3 (3)	C4—Fe1—C10—C9	72.0 (3)
C1—Fe1—C4—C5	−37.63 (18)	C3—Fe1—C10—C9	34.9 (6)
C7—Fe1—C4—C5	−168.5 (3)	C1—Fe1—C10—C9	157.5 (2)
C8—Fe1—C4—C5	158.2 (2)	C7—Fe1—C10—C9	−81.6 (3)
C2—Fe1—C4—C5	−81.55 (19)	C8—Fe1—C10—C9	−38.1 (2)
C3—C4—C5—C1	−0.5 (3)	C5—Fe1—C10—C9	113.8 (2)
Fe1—C4—C5—C1	59.01 (19)	C2—Fe1—C10—C9	−166.2 (3)
C3—C4—C5—Fe1	−59.5 (2)	C12—N1—C11—C1	−150.6 (3)
C2—C1—C5—C4	1.0 (3)	C2—C1—C11—N1	−145.3 (3)
C11—C1—C5—C4	177.2 (3)	C5—C1—C11—N1	39.2 (4)
Fe1—C1—C5—C4	−59.02 (19)	Fe1—C1—C11—N1	−54.1 (4)
C2—C1—C5—Fe1	60.05 (19)	C11—N1—C12—N2	−175.8 (3)
C11—C1—C5—Fe1	−123.8 (3)	C11—N1—C12—S1	4.0 (4)
C9—Fe1—C5—C4	−83.8 (2)	C13—N2—C12—N1	2.1 (4)
C6—Fe1—C5—C4	−167.1 (2)	C13—N2—C12—S1	−177.7 (2)
C10—Fe1—C5—C4	−126.8 (2)	C12—N2—C13—C14	67.5 (4)
C3—Fe1—C5—C4	37.46 (19)	C12—N2—C13—C22	−115.0 (3)
C1—Fe1—C5—C4	119.5 (3)	C22—C13—C14—C15	0.7 (4)
C7—Fe1—C5—C4	158.9 (5)	N2—C13—C14—C15	178.1 (2)
C8—Fe1—C5—C4	−47.2 (4)	C13—C14—C15—C16	−2.2 (4)
C2—Fe1—C5—C4	81.2 (2)	C14—C15—C16—C17	1.3 (5)
C9—Fe1—C5—C1	156.8 (2)	C15—C16—C17—C18	−178.4 (3)
C6—Fe1—C5—C1	73.5 (2)	C15—C16—C17—C22	1.1 (4)
C10—Fe1—C5—C1	113.8 (2)	C16—C17—C18—C19	−178.7 (3)
C4—Fe1—C5—C1	−119.5 (3)	C22—C17—C18—C19	1.9 (4)
C3—Fe1—C5—C1	−82.01 (19)	C17—C18—C19—C20	0.1 (5)
C7—Fe1—C5—C1	39.4 (6)	C18—C19—C20—C21	−1.4 (5)
C8—Fe1—C5—C1	−166.6 (3)	C19—C20—C21—C22	0.7 (5)
C2—Fe1—C5—C1	−38.27 (16)	C14—C13—C22—C21	−178.9 (2)
C9—Fe1—C6—C10	−37.8 (2)	N2—C13—C22—C21	3.6 (4)
C4—Fe1—C6—C10	36.9 (6)	C14—C13—C22—C17	1.7 (4)
C3—Fe1—C6—C10	−165.4 (3)	N2—C13—C22—C17	−175.8 (2)
C1—Fe1—C6—C10	114.7 (2)	C20—C21—C22—C13	−178.2 (3)
C7—Fe1—C6—C10	−119.6 (3)	C20—C21—C22—C17	1.2 (4)
C8—Fe1—C6—C10	−82.2 (3)	C18—C17—C22—C13	177.0 (2)
C5—Fe1—C6—C10	73.2 (3)	C16—C17—C22—C13	−2.5 (4)
C2—Fe1—C6—C10	158.0 (2)	C18—C17—C22—C21	−2.5 (4)
C9—Fe1—C6—C7	81.8 (3)	C16—C17—C22—C21	178.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1ⁱ	0.90 (3)	2.45 (3)	3.326 (3)	167 (2)

Symmetry code: (i) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₇H₁₅N₂S)]
M_r	400.31
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.958 (3), 10.890 (5), 12.357 (5)
α, β, γ (°)	66.886 (6), 78.637 (8), 73.306 (8)
V (Å³)	939.1 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.92
Crystal size (mm)	0.39 × 0.24 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.755, 0.867
No. of measured, independent and observed [I > 2σ(I)] reflections	5178, 3645, 2741
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.105, 1.04
No. of reflections	3645
No. of parameters	241
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.32

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1ⁱ	0.90 (3)	2.45 (3)	3.326 (3)	167 (2)

Symmetry code: (i) −x+2, −y+1, −z.

Acknowledgements

We gratefully acknowledge financial support from the Foundation of Henan Educational Committee (2011B150001) and the Foundation of Henan University of Urban Construction (2010JYB007).

References

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