2-Amino-4-(4-bromo-phen-yl)-6-ferro-cenyl-pyridine-3-carbonitrile.

The title compound, [Fe(C(5)H(5))(C(17)H(11)BrN(3))], was synthesized by the reaction of 4-bromo-benzaldehyde, acetyl-ferrocene and ammonium acetate in an aqueous medium. The crystal packing is stabilized by inter-molecular 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 = 458.14

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.094

S = 1.02

3290 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.50 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S160053680705489X/bq2041Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Fe(C5H5)(C17H11BrN3)]	F(000) = 920
Mr = 458.14	Dx = 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

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

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(Fo2) + (0.0439P)2 + 0.873P] where P = (Fo2 + 2Fc2)/3
3290 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

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	0.88176 (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*

	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)

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)

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

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) .