2-Amino-4-(4-bromo­phen­yl)-6-ferro­cenyl­pyridine-3-carbonitrile

Jia, R.-H.; Tu, S.-J.

doi:10.1107/S160053680705489X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m135

https://doi.org/10.1107/S160053680705489X

Open

access

2-Amino-4-(4-bromophenyl)-6-ferrocenylpyridine-3-carbonitrile

Run-Hong Jia ^a and Shu-Jiang Tu ^b ^*

^aLianyungang Teacher's College, Lianyungang 222006, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
^*Correspondence e-mail: laotu2001@263.net

(Received 16 October 2007; accepted 31 October 2007; online 6 December 2007)

The title compound, [Fe(C₅H₅)(C₁₇H₁₁BrN₃)], was synthesized by the reaction of 4-bromobenzaldehyde, acetylferrocene and ammonium acetate in an aqueous medium. The crystal packing is stabilized by intermolecular N—H⋯N hydrogen bonds. The dihedral angles between the phenyl ring and the pyridine and cyclopentadienyl rings are 51.67 (13) and 12.12 (21)°, respectively.

Related literature

For related literature, see: Alyoubi (2000 ); Desai & Shah (2003 ); Dombrowski et al. (1986 ); Murata et al. (2004 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₇H₁₁BrN₃)]
M_r = 458.14
Monoclinic, P 2₁ /n
a = 12.250 (2) Å
b = 7.4511 (12) Å
c = 20.698 (3) Å
β = 97.729 (3)°
V = 1872.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.95 mm⁻¹
T = 298 (2) K
0.16 × 0.11 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.650, T_max = 0.820
9276 measured reflections
3290 independent reflections
2327 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.094
S = 1.02
3290 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯N3ⁱ	0.86	2.29	3.050 (5)	148
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680705489X/bq2041sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680705489X/bq2041Isup2.hkl

checkCIF report

Comment top

Metallocenes are known to exhibit a wide range of biological activity. Among them, ferrocene has attracted special attention since it is neutral, chemically stable, non-toxic and able to cross cell membranes (Dombrowski et al., 1986). In fact, it is now well established that the incorporation of ferrocene units in organic molecules introduces significant and new properties in these materials. In addition, it has been demonstrated that molecules containing cyanopyridine moiety may be able to work as ligands towards transition-metal ions (Alyoubi, 2000), new drugs (Murata et al., 2004 and Desai et al., 2003), and significant intermediates for the synthesis of important vitamins such as nicotinic acids and nicotinamides. For these reasons, the synthesis of new compounds containing cyanopyridine derivatives is strongly desired. In this paper we report the crystal structure of the title compound (I).

In the crystal structure, the dihedral angle between the C1/C2/C3/C4/C5/N1 plane and the C17—C22 benzene ring is 51.65 (13)°.The dihedral angle between the C1/C2/C3/C4/C5/N1 plane and the C11—C16 ring is 12.21 (14)°. The molecules are connected via N—H···N hydrogen bonds, forming a three-dimensional network (Fig. 2).

Related literature top

For related literature, see: Alyoubi (2000); Desai & Shah (2003); Dombrowski et al. (1986); Murata et al. (2004).

Experimental top

Compound (I) was prepared by the reaction of 4-bromobenzaldehyde (2 mmol), malononitrile (2 mmol), acetylferrocene (2 mmol) and ammonium acetate (4 mmol) in water (2 ml). Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a 95% aqueous ethanol solution (yield 94%; m.p. >573 K). IR (cm^-1): 3457, 3354, 2211; ¹H NMR (DMSO-d₆): 4.10 (5H, s, ferrocenyl), 4.50 (2H, s, ferrocenyl), 5.04 (2H, s, ferrocenyl), 6.83 (2H, brs, NH₂), 6.94 (1H, s, ArH), 7.60 (2H, d, J = 8.0 Hz, ArH), 7.77 (2H, d, J = 8.0 Hz, ArH).7.87 (2H, brs, NH₂), 7.88–8.01 (4H, m, ArH), 11.85 (1H, s, NH).

Structure description top

For related literature, see: Alyoubi (2000); Desai & Shah (2003); Dombrowski et al. (1986); Murata et al. (2004).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1999).

Figures top

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

2-Amino-4-(4-bromophenyl)-6-ferrocenylpyridine-3-carbonitrile top

Crystal data top

[Fe(C₅H₅)(C₁₇H₁₁BrN₃)]	F(000) = 920
M_r = 458.14	D_x = 1.625 Mg m⁻³
Monoclinic, P2₁/n	Melting point > 573 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.250 (2) Å	Cell parameters from 9276 reflections
b = 7.4511 (12) Å	θ = 1.8–25.0°
c = 20.698 (3) Å	µ = 2.95 mm⁻¹
β = 97.729 (3)°	T = 298 K
V = 1872.2 (5) Å³	Block, red
Z = 4	0.16 × 0.11 × 0.07 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3290 independent reflections
Radiation source: fine-focus sealed tube	2327 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
phi and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −14→12
T_min = 0.650, T_max = 0.820	k = −8→8
9276 measured reflections	l = −21→24

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0439P)² + 0.873P] where P = (F_o² + 2F_c²)/3
3290 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₇H₁₁BrN₃)]	V = 1872.2 (5) Å³
M_r = 458.14	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.250 (2) Å	µ = 2.95 mm⁻¹
b = 7.4511 (12) Å	T = 298 K
c = 20.698 (3) Å	0.16 × 0.11 × 0.07 mm
β = 97.729 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3290 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2327 reflections with I > 2σ(I)
T_min = 0.650, T_max = 0.820	R_int = 0.042
9276 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.02	Δρ_max = 0.41 e Å⁻³
3290 reflections	Δρ_min = −0.50 e Å⁻³
244 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	0.88176 (4)	0.56744 (7)	0.10748 (3)	0.03294 (17)
Br1	1.31762 (4)	−0.46355 (6)	0.38737 (3)	0.06095 (19)
N1	0.8559 (2)	0.4500 (4)	0.27746 (15)	0.0335 (7)
N2	0.8621 (3)	0.5510 (4)	0.38201 (16)	0.0441 (9)
H2A	0.8136	0.6301	0.3678	0.053*
H2B	0.8871	0.5466	0.4228	0.053*
N3	1.0484 (3)	0.3011 (5)	0.48388 (19)	0.0596 (11)
C1	0.8991 (3)	0.4337 (5)	0.34017 (18)	0.0319 (9)
C2	0.9785 (3)	0.3014 (5)	0.36174 (18)	0.0302 (8)
C3	1.0146 (3)	0.1847 (5)	0.31590 (18)	0.0302 (9)
C4	0.9720 (3)	0.2070 (5)	0.25112 (18)	0.0313 (9)
H4	0.9956	0.1339	0.2193	0.038*
C5	0.8928 (3)	0.3408 (5)	0.23362 (17)	0.0274 (8)
C6	0.8419 (3)	0.3651 (5)	0.16587 (17)	0.0295 (8)
C7	0.7494 (3)	0.4767 (5)	0.14559 (18)	0.0328 (9)
H7	0.7103	0.5424	0.1731	0.039*
C8	0.7267 (3)	0.4714 (5)	0.0769 (2)	0.0404 (10)
H8	0.6696	0.5310	0.0514	0.048*
C9	0.8063 (3)	0.3594 (5)	0.05372 (19)	0.0384 (9)
H9	0.8107	0.3334	0.0102	0.046*
C10	0.8781 (3)	0.2935 (5)	0.10802 (18)	0.0343 (9)
H10	0.9379	0.2175	0.1064	0.041*
C11	1.0377 (4)	0.6526 (6)	0.1005 (2)	0.0542 (12)
H11	1.0979	0.5798	0.0960	0.065*
C12	1.0040 (4)	0.7097 (6)	0.1601 (3)	0.0596 (13)
H12	1.0381	0.6819	0.2018	0.072*
C13	0.9095 (4)	0.8163 (6)	0.1444 (3)	0.0597 (13)
H13	0.8697	0.8711	0.1741	0.072*
C14	0.8852 (4)	0.8261 (6)	0.0762 (3)	0.0586 (13)
H14	0.8269	0.8885	0.0530	0.070*
C15	0.9639 (4)	0.7257 (6)	0.0495 (2)	0.0533 (12)
H15	0.9671	0.7098	0.0053	0.064*
C16	1.0201 (3)	0.2954 (5)	0.4291 (2)	0.0395 (10)
C17	1.0911 (3)	0.0326 (5)	0.33629 (17)	0.0306 (8)
C18	1.1829 (3)	0.0036 (5)	0.3047 (2)	0.0439 (10)
H18	1.1986	0.0831	0.2725	0.053*
C19	1.2509 (3)	−0.1418 (6)	0.3206 (2)	0.0461 (11)
H19	1.3125	−0.1601	0.2996	0.055*
C20	1.2267 (3)	−0.2594 (5)	0.3678 (2)	0.0389 (10)
C21	1.1376 (3)	−0.2323 (5)	0.3997 (2)	0.0484 (11)
H21	1.1226	−0.3120	0.4320	0.058*
C22	1.0702 (3)	−0.0868 (5)	0.3841 (2)	0.0455 (11)
H22	1.0097	−0.0686	0.4060	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0303 (3)	0.0277 (3)	0.0417 (3)	−0.0076 (2)	0.0078 (2)	0.0011 (2)
Br1	0.0584 (3)	0.0489 (3)	0.0780 (4)	0.0306 (2)	0.0181 (3)	0.0102 (3)
N1	0.0335 (18)	0.0312 (17)	0.0363 (18)	0.0084 (14)	0.0065 (14)	−0.0016 (15)
N2	0.048 (2)	0.045 (2)	0.0387 (19)	0.0278 (17)	0.0043 (16)	−0.0063 (16)
N3	0.070 (3)	0.065 (3)	0.041 (2)	0.031 (2)	−0.002 (2)	−0.005 (2)
C1	0.028 (2)	0.030 (2)	0.038 (2)	0.0045 (16)	0.0073 (17)	−0.0006 (18)
C2	0.030 (2)	0.0270 (19)	0.033 (2)	0.0053 (16)	0.0019 (16)	−0.0024 (16)
C3	0.027 (2)	0.0275 (19)	0.037 (2)	−0.0008 (16)	0.0081 (17)	0.0005 (17)
C4	0.027 (2)	0.0300 (19)	0.039 (2)	0.0041 (16)	0.0100 (17)	−0.0031 (17)
C5	0.026 (2)	0.0267 (19)	0.031 (2)	−0.0012 (15)	0.0091 (16)	−0.0010 (16)
C6	0.028 (2)	0.0263 (18)	0.035 (2)	−0.0034 (16)	0.0058 (16)	−0.0018 (17)
C7	0.029 (2)	0.035 (2)	0.036 (2)	−0.0065 (17)	0.0084 (16)	−0.0015 (17)
C8	0.033 (2)	0.040 (2)	0.048 (3)	−0.0059 (18)	0.0007 (18)	0.005 (2)
C9	0.041 (2)	0.041 (2)	0.034 (2)	−0.013 (2)	0.0084 (18)	−0.0028 (19)
C10	0.037 (2)	0.0253 (19)	0.042 (2)	−0.0050 (17)	0.0114 (18)	−0.0030 (18)
C11	0.036 (3)	0.052 (3)	0.075 (4)	−0.018 (2)	0.012 (2)	0.008 (3)
C12	0.060 (3)	0.052 (3)	0.064 (3)	−0.035 (3)	−0.005 (3)	0.003 (2)
C13	0.067 (4)	0.035 (2)	0.080 (4)	−0.021 (2)	0.023 (3)	−0.012 (3)
C14	0.055 (3)	0.035 (2)	0.088 (4)	−0.006 (2)	0.020 (3)	0.011 (3)
C15	0.053 (3)	0.050 (3)	0.059 (3)	−0.017 (2)	0.020 (2)	0.011 (2)
C16	0.042 (3)	0.037 (2)	0.039 (3)	0.0170 (19)	0.006 (2)	−0.0008 (19)
C17	0.028 (2)	0.0270 (19)	0.037 (2)	0.0028 (16)	0.0087 (16)	−0.0027 (17)
C18	0.048 (3)	0.038 (2)	0.049 (3)	0.0091 (19)	0.018 (2)	0.006 (2)
C19	0.038 (2)	0.047 (2)	0.058 (3)	0.011 (2)	0.024 (2)	0.003 (2)
C20	0.033 (2)	0.032 (2)	0.052 (3)	0.0118 (17)	0.0080 (19)	−0.003 (2)
C21	0.050 (3)	0.039 (2)	0.061 (3)	0.012 (2)	0.023 (2)	0.013 (2)
C22	0.040 (2)	0.042 (2)	0.059 (3)	0.012 (2)	0.024 (2)	0.007 (2)

Geometric parameters (Å, º) top

Fe1—C7	2.013 (4)	C7—C8	1.412 (5)
Fe1—C13	2.017 (4)	C7—H7	0.9300
Fe1—C12	2.028 (4)	C8—C9	1.416 (5)
Fe1—C6	2.033 (4)	C8—H8	0.9300
Fe1—C14	2.035 (4)	C9—C10	1.419 (5)
Fe1—C11	2.037 (4)	C9—H9	0.9300
Fe1—C15	2.041 (4)	C10—H10	0.9300
Fe1—C10	2.042 (4)	C11—C15	1.404 (6)
Fe1—C8	2.049 (4)	C11—C12	1.417 (6)
Fe1—C9	2.054 (4)	C11—H11	0.9300
Br1—C20	1.897 (4)	C12—C13	1.406 (6)
N1—C1	1.340 (5)	C12—H12	0.9300
N1—C5	1.342 (4)	C13—C14	1.404 (7)
N2—C1	1.351 (4)	C13—H13	0.9300
N2—H2A	0.8600	C14—C15	1.392 (6)
N2—H2B	0.8600	C14—H14	0.9300
N3—C16	1.140 (5)	C15—H15	0.9300
C1—C2	1.415 (5)	C17—C22	1.380 (5)
C2—C3	1.402 (5)	C17—C18	1.392 (5)
C2—C16	1.420 (6)	C18—C19	1.379 (5)
C3—C4	1.382 (5)	C18—H18	0.9300
C3—C17	1.495 (5)	C19—C20	1.374 (5)
C4—C5	1.404 (5)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.365 (5)
C5—C6	1.468 (5)	C21—C22	1.375 (5)
C6—C7	1.423 (5)	C21—H21	0.9300
C6—C10	1.435 (5)	C22—H22	0.9300

C7—Fe1—C13	105.30 (18)	C6—C7—Fe1	70.1 (2)
C7—Fe1—C12	122.73 (18)	C8—C7—H7	125.6
C13—Fe1—C12	40.67 (19)	C6—C7—H7	125.6
C7—Fe1—C6	41.17 (14)	Fe1—C7—H7	124.8
C13—Fe1—C6	119.91 (18)	C7—C8—C9	107.8 (3)
C12—Fe1—C6	106.72 (17)	C7—C8—Fe1	68.3 (2)
C7—Fe1—C14	119.64 (17)	C9—C8—Fe1	70.0 (2)
C13—Fe1—C14	40.54 (18)	C7—C8—H8	126.1
C12—Fe1—C14	68.3 (2)	C9—C8—H8	126.1
C6—Fe1—C14	155.28 (18)	Fe1—C8—H8	127.2
C7—Fe1—C11	160.93 (17)	C8—C9—C10	108.5 (3)
C13—Fe1—C11	68.2 (2)	C8—C9—Fe1	69.6 (2)
C12—Fe1—C11	40.81 (18)	C10—C9—Fe1	69.3 (2)
C6—Fe1—C11	125.17 (17)	C8—C9—H9	125.7
C14—Fe1—C11	67.84 (19)	C10—C9—H9	125.7
C7—Fe1—C15	155.64 (17)	Fe1—C9—H9	127.0
C13—Fe1—C15	67.7 (2)	C9—C10—C6	107.7 (3)
C12—Fe1—C15	68.07 (19)	C9—C10—Fe1	70.2 (2)
C6—Fe1—C15	162.71 (17)	C6—C10—Fe1	69.1 (2)
C14—Fe1—C15	39.94 (17)	C9—C10—H10	126.1
C11—Fe1—C15	40.27 (17)	C6—C10—H10	126.1
C7—Fe1—C10	69.07 (15)	Fe1—C10—H10	126.2
C13—Fe1—C10	156.9 (2)	C15—C11—C12	107.7 (5)
C12—Fe1—C10	122.33 (18)	C15—C11—Fe1	70.1 (2)
C6—Fe1—C10	41.23 (14)	C12—C11—Fe1	69.3 (2)
C14—Fe1—C10	161.78 (19)	C15—C11—H11	126.2
C11—Fe1—C10	109.48 (18)	C12—C11—H11	126.2
C15—Fe1—C10	126.43 (17)	Fe1—C11—H11	126.1
C7—Fe1—C8	40.67 (15)	C13—C12—C11	107.2 (4)
C13—Fe1—C8	122.68 (19)	C13—C12—Fe1	69.2 (2)
C12—Fe1—C8	159.3 (2)	C11—C12—Fe1	69.9 (2)
C6—Fe1—C8	68.75 (15)	C13—C12—H12	126.4
C14—Fe1—C8	106.87 (18)	C11—C12—H12	126.4
C11—Fe1—C8	157.92 (18)	Fe1—C12—H12	126.0
C15—Fe1—C8	122.02 (18)	C14—C13—C12	108.6 (5)
C10—Fe1—C8	68.44 (16)	C14—C13—Fe1	70.4 (3)
C7—Fe1—C9	68.36 (15)	C12—C13—Fe1	70.1 (2)
C13—Fe1—C9	160.0 (2)	C14—C13—H13	125.7
C12—Fe1—C9	158.7 (2)	C12—C13—H13	125.7
C6—Fe1—C9	68.62 (15)	Fe1—C13—H13	125.3
C14—Fe1—C9	124.71 (19)	C15—C14—C13	107.8 (5)
C11—Fe1—C9	123.72 (18)	C15—C14—Fe1	70.3 (2)
C15—Fe1—C9	109.84 (17)	C13—C14—Fe1	69.0 (3)
C10—Fe1—C9	40.53 (14)	C15—C14—H14	126.1
C8—Fe1—C9	40.36 (15)	C13—C14—H14	126.1
C1—N1—C5	118.3 (3)	Fe1—C14—H14	126.2
C1—N2—H2A	120.0	C14—C15—C11	108.7 (4)
C1—N2—H2B	120.0	C14—C15—Fe1	69.8 (2)
H2A—N2—H2B	120.0	C11—C15—Fe1	69.7 (2)
N1—C1—N2	116.1 (3)	C14—C15—H15	125.6
N1—C1—C2	122.3 (3)	C11—C15—H15	125.6
N2—C1—C2	121.6 (3)	Fe1—C15—H15	126.5
C3—C2—C1	119.0 (3)	N3—C16—C2	174.9 (4)
C3—C2—C16	122.8 (3)	C22—C17—C18	118.5 (3)
C1—C2—C16	118.2 (3)	C22—C17—C3	121.4 (3)
C4—C3—C2	118.0 (3)	C18—C17—C3	120.0 (3)
C4—C3—C17	120.4 (3)	C19—C18—C17	120.7 (4)
C2—C3—C17	121.5 (3)	C19—C18—H18	119.7
C3—C4—C5	119.6 (3)	C17—C18—H18	119.7
C3—C4—H4	120.2	C20—C19—C18	119.3 (4)
C5—C4—H4	120.2	C20—C19—H19	120.4
N1—C5—C4	122.7 (3)	C18—C19—H19	120.4
N1—C5—C6	115.6 (3)	C21—C20—C19	120.9 (4)
C4—C5—C6	121.6 (3)	C21—C20—Br1	120.0 (3)
C7—C6—C10	107.1 (3)	C19—C20—Br1	119.1 (3)
C7—C6—C5	125.0 (3)	C20—C21—C22	119.8 (4)
C10—C6—C5	127.7 (3)	C20—C21—H21	120.1
C7—C6—Fe1	68.7 (2)	C22—C21—H21	120.1
C10—C6—Fe1	69.7 (2)	C21—C22—C17	120.9 (4)
C5—C6—Fe1	123.7 (2)	C21—C22—H22	119.5
C8—C7—C6	108.8 (3)	C17—C22—H22	119.5
C8—C7—Fe1	71.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N3ⁱ	0.86	2.29	3.050 (5)	148

Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₇H₁₁BrN₃)]
M_r	458.14
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	12.250 (2), 7.4511 (12), 20.698 (3)
β (°)	97.729 (3)
V (Å³)	1872.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.95
Crystal size (mm)	0.16 × 0.11 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.650, 0.820
No. of measured, independent and observed [I > 2σ(I)] reflections	9276, 3290, 2327
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.094, 1.02
No. of reflections	3290
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.50

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N3ⁱ	0.86	2.29	3.050 (5)	148.0

Symmetry code: (i) −x+2, −y+1, −z+1.

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant No. 20672090) and the Natural Science Foundation of the Jiangsu Province (grant No. BK2006033) for financial support.

References

Alyoubi, A. O. (2000). Spectrochim. Acta Part A, 56, 2397–2404. CrossRef Google Scholar
Bruker (1998). SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Desai, J. M. & Shah, V. H. (2003). Indian J. Chem. Sect. B, 42, 382–385. Google Scholar
Dombrowski, K. E., Baldwin, W. & Sheats, J. E. (1986). J. Organomet. Chem. 302, 281–306. CrossRef CAS Web of Science Google Scholar
Murata, T., Shimada, M., Sakakibara, S., Yoshino, T., Masuda, T., Shintani, T., Sato, H., Koriyama, Y., Fukushima, K., Nunami, N., Yamauchi, M., Fuchikami, K., Komura, H., Watanabe, A., Ziegelbauer, K. B., Bacon, K. B. & Lowinger, T. B. (2004). Bioorg. Med. Chem. Lett. 14, 4019–4022. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar