metal-organic compounds
2-Amino-4-(4-chlorophenyl)-6-ferrocenylpyridine-3-carbonitrile
aDepartment of Public Health, Xuzhou Medical College, Xuzhou 221000, 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
In the molecule of the title compound, [Fe(C5H5)(C17H11ClN3)], the dihedral angles between the two five–membered rings and between the two six-membered rings are 3.28 (4) and 51.33 (4)°, respectively. In the intermolecular N—H⋯N hydrogen bonds link the molecules into centrosymmetric dimers.
Related literature
For general background, see: Dombrowski et al. (1986); Alyoubi (2000); Desai & Shah (2003); Murata et al. (2004).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1998); cell SAINT (Bruker, 1999); 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
10.1107/S1600536808008714/hk2443sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808008714/hk2443Isup2.hkl
Compound (I) was prepared by the reaction of 4-chlorobenzaldehyde (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 analysis were obtained by slow evaporation of an aqueous ethanol solution (95%) (yield; 95%, m.p. 548-550 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), 6.81 (2H, brs, NH2), 6.95 (1H, s, ArH), 7.64 (2H, d, J = 8.4 Hz, ArH), 7.68 (2H, d, J = 8.4 Hz, ArH).7.87 (2H, brs, NH2), 7.88–8.01 (4H, m, ArH), 11.85 (1H, s, NH).
H atoms were positioned geometrically, with N-H = 0.86 Å (for NH2) and C-H = 0.93 Å for aromatic H,and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C,N).
Data collection: SMART (Bruker, 1998); cell
SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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).[Fe(C5H5)(C17H11ClN3)] | F(000) = 848 |
Mr = 413.68 | Dx = 1.482 Mg m−3 |
Monoclinic, P21/n | Melting point = 548–550 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 12.1517 (13) Å | Cell parameters from 2405 reflections |
b = 7.4214 (11) Å | θ = 2.9–26.2° |
c = 20.742 (2) Å | µ = 0.97 mm−1 |
β = 97.691 (2)° | T = 298 K |
V = 1853.7 (4) Å3 | Block, red |
Z = 4 | 0.20 × 0.15 × 0.09 mm |
Bruker SMART CCD area-detector diffractometer | 3260 independent reflections |
Radiation source: fine-focus sealed tube | 2298 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.830, Tmax = 0.918 | k = −8→6 |
8876 measured reflections | l = −24→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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0178P)2 + 2.3504P] where P = (Fo2 + 2Fc2)/3 |
3260 reflections | (Δ/σ)max < 0.001 |
244 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
[Fe(C5H5)(C17H11ClN3)] | V = 1853.7 (4) Å3 |
Mr = 413.68 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.1517 (13) Å | µ = 0.97 mm−1 |
b = 7.4214 (11) Å | T = 298 K |
c = 20.742 (2) Å | 0.20 × 0.15 × 0.09 mm |
β = 97.691 (2)° |
Bruker SMART CCD area-detector diffractometer | 3260 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2298 reflections with I > 2σ(I) |
Tmin = 0.830, Tmax = 0.918 | Rint = 0.041 |
8876 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.44 e Å−3 |
3260 reflections | Δρmin = −0.43 e Å−3 |
244 parameters |
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 > 2sigma(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 | 0.38223 (4) | 0.42499 (7) | 0.10732 (3) | 0.03424 (16) | |
Cl1 | 0.81792 (10) | 1.44271 (17) | 0.38672 (6) | 0.0694 (4) | |
N1 | 0.3585 (2) | 0.5432 (4) | 0.27711 (13) | 0.0335 (7) | |
N2 | 0.3644 (2) | 0.4443 (4) | 0.38140 (14) | 0.0450 (8) | |
H2A | 0.3154 | 0.3649 | 0.3672 | 0.054* | |
H2B | 0.3892 | 0.4491 | 0.4222 | 0.054* | |
N3 | 0.5500 (3) | 0.6983 (5) | 0.48341 (17) | 0.0652 (12) | |
C1 | 0.4019 (3) | 0.5604 (5) | 0.33992 (16) | 0.0321 (8) | |
C2 | 0.4807 (3) | 0.6949 (5) | 0.36089 (16) | 0.0301 (8) | |
C3 | 0.5168 (3) | 0.8132 (5) | 0.31540 (17) | 0.0307 (8) | |
C4 | 0.4739 (3) | 0.7885 (5) | 0.25086 (17) | 0.0309 (8) | |
H4 | 0.4977 | 0.8613 | 0.2189 | 0.037* | |
C5 | 0.3950 (3) | 0.6543 (5) | 0.23368 (16) | 0.0292 (8) | |
C6 | 0.3441 (3) | 0.6283 (5) | 0.16610 (16) | 0.0287 (8) | |
C7 | 0.3802 (3) | 0.6998 (5) | 0.10848 (18) | 0.0366 (9) | |
H7 | 0.4408 | 0.7755 | 0.1070 | 0.044* | |
C8 | 0.3080 (3) | 0.6355 (5) | 0.05402 (17) | 0.0396 (10) | |
H8 | 0.3125 | 0.6617 | 0.0106 | 0.048* | |
C9 | 0.2277 (3) | 0.5243 (5) | 0.07769 (17) | 0.0390 (10) | |
H9 | 0.1701 | 0.4648 | 0.0523 | 0.047* | |
C10 | 0.2493 (3) | 0.5186 (5) | 0.14592 (17) | 0.0345 (9) | |
H10 | 0.2088 | 0.4543 | 0.1732 | 0.041* | |
C11 | 0.5039 (4) | 0.2760 (6) | 0.1590 (2) | 0.0615 (13) | |
H11 | 0.5385 | 0.3005 | 0.2008 | 0.074* | |
C12 | 0.5390 (3) | 0.3359 (6) | 0.1002 (2) | 0.0582 (13) | |
H12 | 0.6003 | 0.4081 | 0.0964 | 0.070* | |
C13 | 0.4640 (4) | 0.2662 (6) | 0.0484 (2) | 0.0562 (12) | |
H13 | 0.4672 | 0.2835 | 0.0042 | 0.067* | |
C14 | 0.3841 (4) | 0.1665 (6) | 0.0753 (3) | 0.0594 (13) | |
H14 | 0.3249 | 0.1057 | 0.0519 | 0.071* | |
C15 | 0.4071 (4) | 0.1726 (6) | 0.1426 (3) | 0.0648 (14) | |
H15 | 0.3658 | 0.1178 | 0.1717 | 0.078* | |
C16 | 0.5217 (3) | 0.7025 (5) | 0.42883 (19) | 0.0409 (10) | |
C17 | 0.5934 (3) | 0.9656 (5) | 0.33533 (17) | 0.0308 (8) | |
C18 | 0.5737 (3) | 1.0847 (6) | 0.38359 (19) | 0.0469 (10) | |
H18 | 0.5127 | 1.0663 | 0.4055 | 0.056* | |
C19 | 0.6424 (3) | 1.2308 (6) | 0.4002 (2) | 0.0489 (11) | |
H19 | 0.6276 | 1.3099 | 0.4328 | 0.059* | |
C20 | 0.7325 (3) | 1.2576 (5) | 0.36813 (19) | 0.0429 (10) | |
C21 | 0.7559 (3) | 1.1393 (6) | 0.3206 (2) | 0.0487 (11) | |
H21 | 0.8182 | 1.1567 | 0.2998 | 0.058* | |
C22 | 0.6861 (3) | 0.9946 (6) | 0.30423 (19) | 0.0450 (10) | |
H22 | 0.7015 | 0.9155 | 0.2718 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0363 (3) | 0.0281 (3) | 0.0382 (3) | 0.0077 (3) | 0.0046 (2) | −0.0010 (3) |
Cl1 | 0.0680 (7) | 0.0544 (8) | 0.0859 (9) | −0.0359 (6) | 0.0103 (6) | −0.0084 (7) |
N1 | 0.0387 (16) | 0.0311 (18) | 0.0301 (15) | −0.0057 (15) | 0.0022 (13) | 0.0036 (15) |
N2 | 0.0533 (19) | 0.049 (2) | 0.0304 (16) | −0.0262 (18) | −0.0027 (14) | 0.0062 (18) |
N3 | 0.085 (3) | 0.067 (3) | 0.039 (2) | −0.033 (2) | −0.0095 (19) | 0.010 (2) |
C1 | 0.0330 (18) | 0.033 (2) | 0.0308 (19) | −0.0026 (18) | 0.0045 (15) | 0.0014 (19) |
C2 | 0.0306 (19) | 0.029 (2) | 0.0293 (19) | −0.0047 (16) | 0.0005 (16) | −0.0001 (17) |
C3 | 0.0280 (18) | 0.027 (2) | 0.038 (2) | −0.0002 (16) | 0.0048 (16) | −0.0007 (17) |
C4 | 0.0320 (19) | 0.029 (2) | 0.032 (2) | −0.0036 (16) | 0.0054 (16) | 0.0039 (17) |
C5 | 0.0295 (18) | 0.0260 (19) | 0.0326 (19) | 0.0050 (16) | 0.0056 (16) | 0.0004 (17) |
C6 | 0.0323 (19) | 0.027 (2) | 0.0264 (18) | 0.0038 (16) | 0.0022 (15) | 0.0028 (16) |
C7 | 0.042 (2) | 0.026 (2) | 0.042 (2) | 0.0062 (19) | 0.0067 (18) | 0.006 (2) |
C8 | 0.050 (2) | 0.042 (2) | 0.0275 (19) | 0.011 (2) | 0.0043 (18) | 0.0011 (19) |
C9 | 0.039 (2) | 0.040 (2) | 0.036 (2) | 0.0075 (18) | −0.0011 (17) | −0.0050 (19) |
C10 | 0.0318 (19) | 0.035 (2) | 0.036 (2) | 0.0041 (17) | 0.0018 (16) | −0.0006 (18) |
C11 | 0.065 (3) | 0.054 (3) | 0.061 (3) | 0.031 (3) | −0.008 (3) | 0.001 (3) |
C12 | 0.039 (2) | 0.052 (3) | 0.084 (4) | 0.018 (2) | 0.006 (2) | −0.009 (3) |
C13 | 0.058 (3) | 0.049 (3) | 0.064 (3) | 0.014 (2) | 0.017 (2) | −0.017 (3) |
C14 | 0.065 (3) | 0.033 (3) | 0.079 (4) | 0.007 (2) | 0.006 (3) | −0.011 (3) |
C15 | 0.075 (3) | 0.038 (3) | 0.083 (4) | 0.017 (3) | 0.017 (3) | 0.015 (3) |
C16 | 0.048 (2) | 0.036 (2) | 0.037 (2) | −0.0157 (19) | 0.0013 (19) | 0.006 (2) |
C17 | 0.0309 (18) | 0.026 (2) | 0.0358 (19) | −0.0052 (16) | 0.0041 (15) | 0.0030 (17) |
C18 | 0.043 (2) | 0.044 (2) | 0.057 (3) | −0.014 (2) | 0.0189 (19) | −0.012 (2) |
C19 | 0.053 (3) | 0.040 (2) | 0.056 (3) | −0.011 (2) | 0.013 (2) | −0.012 (2) |
C20 | 0.043 (2) | 0.039 (2) | 0.046 (2) | −0.014 (2) | 0.0060 (19) | 0.000 (2) |
C21 | 0.041 (2) | 0.049 (3) | 0.060 (3) | −0.013 (2) | 0.019 (2) | 0.002 (2) |
C22 | 0.045 (2) | 0.045 (2) | 0.046 (2) | −0.008 (2) | 0.0123 (19) | −0.004 (2) |
Fe1—C15 | 2.019 (5) | C7—C8 | 1.417 (5) |
Fe1—C10 | 2.020 (3) | C7—H7 | 0.9300 |
Fe1—C14 | 2.031 (4) | C8—C9 | 1.415 (5) |
Fe1—C6 | 2.032 (3) | C8—H8 | 0.9300 |
Fe1—C11 | 2.033 (4) | C9—C10 | 1.405 (5) |
Fe1—C9 | 2.034 (4) | C9—H9 | 0.9300 |
Fe1—C7 | 2.040 (4) | C10—H10 | 0.9300 |
Fe1—C12 | 2.040 (4) | C11—C15 | 1.408 (6) |
Fe1—C13 | 2.048 (4) | C11—C12 | 1.415 (6) |
Fe1—C8 | 2.052 (4) | C11—H11 | 0.9300 |
Cl1—C20 | 1.734 (4) | C12—C13 | 1.412 (6) |
N1—C5 | 1.339 (4) | C12—H12 | 0.9300 |
N1—C1 | 1.344 (4) | C13—C14 | 1.395 (6) |
N2—C1 | 1.340 (4) | C13—H13 | 0.9300 |
N2—H2A | 0.8600 | C14—C15 | 1.385 (6) |
N2—H2B | 0.8600 | C14—H14 | 0.9300 |
N3—C16 | 1.139 (4) | C15—H15 | 0.9300 |
C1—C2 | 1.411 (5) | C17—C18 | 1.380 (5) |
C2—C3 | 1.401 (5) | C17—C22 | 1.388 (5) |
C2—C16 | 1.432 (5) | C18—C19 | 1.384 (5) |
C3—C4 | 1.382 (5) | C18—H18 | 0.9300 |
C3—C17 | 1.488 (5) | C19—C20 | 1.369 (5) |
C4—C5 | 1.396 (5) | C19—H19 | 0.9300 |
C4—H4 | 0.9300 | C20—C21 | 1.377 (5) |
C5—C6 | 1.467 (4) | C21—C22 | 1.383 (5) |
C6—C10 | 1.426 (5) | C21—H21 | 0.9300 |
C6—C7 | 1.429 (5) | C22—H22 | 0.9300 |
C15—Fe1—C10 | 105.34 (18) | C6—C7—Fe1 | 69.2 (2) |
C15—Fe1—C14 | 40.01 (18) | C8—C7—H7 | 125.8 |
C10—Fe1—C14 | 119.93 (18) | C6—C7—H7 | 125.8 |
C15—Fe1—C6 | 120.45 (18) | Fe1—C7—H7 | 126.4 |
C10—Fe1—C6 | 41.22 (13) | C9—C8—C7 | 107.6 (3) |
C14—Fe1—C6 | 155.60 (18) | C9—C8—Fe1 | 69.1 (2) |
C15—Fe1—C11 | 40.67 (18) | C7—C8—Fe1 | 69.3 (2) |
C10—Fe1—C11 | 122.83 (18) | C9—C8—H8 | 126.2 |
C14—Fe1—C11 | 67.62 (19) | C7—C8—H8 | 126.2 |
C6—Fe1—C11 | 107.21 (16) | Fe1—C8—H8 | 127.0 |
C15—Fe1—C9 | 122.21 (19) | C10—C9—C8 | 108.8 (3) |
C10—Fe1—C9 | 40.55 (13) | C10—C9—Fe1 | 69.2 (2) |
C14—Fe1—C9 | 107.10 (17) | C8—C9—Fe1 | 70.4 (2) |
C6—Fe1—C9 | 68.69 (14) | C10—C9—H9 | 125.6 |
C11—Fe1—C9 | 158.94 (19) | C8—C9—H9 | 125.6 |
C15—Fe1—C7 | 157.7 (2) | Fe1—C9—H9 | 126.4 |
C10—Fe1—C7 | 68.88 (15) | C9—C10—C6 | 108.3 (3) |
C14—Fe1—C7 | 161.62 (19) | C9—C10—Fe1 | 70.3 (2) |
C6—Fe1—C7 | 41.10 (13) | C6—C10—Fe1 | 69.86 (19) |
C11—Fe1—C7 | 123.14 (18) | C9—C10—H10 | 125.9 |
C9—Fe1—C7 | 68.23 (15) | C6—C10—H10 | 125.9 |
C15—Fe1—C12 | 68.25 (19) | Fe1—C10—H10 | 125.6 |
C10—Fe1—C12 | 160.75 (17) | C15—C11—C12 | 107.5 (4) |
C14—Fe1—C12 | 67.58 (19) | C15—C11—Fe1 | 69.1 (2) |
C6—Fe1—C12 | 125.06 (16) | C12—C11—Fe1 | 69.9 (2) |
C11—Fe1—C12 | 40.67 (17) | C15—C11—H11 | 126.2 |
C9—Fe1—C12 | 158.22 (17) | C12—C11—H11 | 126.2 |
C7—Fe1—C12 | 109.75 (18) | Fe1—C11—H11 | 126.3 |
C15—Fe1—C13 | 67.7 (2) | C13—C12—C11 | 107.6 (4) |
C10—Fe1—C13 | 155.78 (16) | C13—C12—Fe1 | 70.1 (2) |
C14—Fe1—C13 | 40.00 (17) | C11—C12—Fe1 | 69.4 (2) |
C6—Fe1—C13 | 162.41 (16) | C13—C12—H12 | 126.2 |
C11—Fe1—C13 | 67.98 (19) | C11—C12—H12 | 126.2 |
C9—Fe1—C13 | 122.00 (16) | Fe1—C12—H12 | 125.9 |
C7—Fe1—C13 | 126.16 (18) | C14—C13—C12 | 107.5 (4) |
C12—Fe1—C13 | 40.39 (16) | C14—C13—Fe1 | 69.3 (2) |
C15—Fe1—C8 | 159.28 (19) | C12—C13—Fe1 | 69.5 (2) |
C10—Fe1—C8 | 68.55 (15) | C14—C13—H13 | 126.2 |
C14—Fe1—C8 | 124.52 (18) | C12—C13—H13 | 126.2 |
C6—Fe1—C8 | 68.82 (13) | Fe1—C13—H13 | 126.5 |
C11—Fe1—C8 | 159.14 (19) | C15—C14—C13 | 109.2 (5) |
C9—Fe1—C8 | 40.52 (14) | C15—C14—Fe1 | 69.5 (3) |
C7—Fe1—C8 | 40.53 (14) | C13—C14—Fe1 | 70.7 (3) |
C12—Fe1—C8 | 123.74 (18) | C15—C14—H14 | 125.4 |
C13—Fe1—C8 | 109.26 (17) | C13—C14—H14 | 125.4 |
C5—N1—C1 | 118.1 (3) | Fe1—C14—H14 | 126.0 |
C1—N2—H2A | 120.0 | C14—C15—C11 | 108.1 (5) |
C1—N2—H2B | 120.0 | C14—C15—Fe1 | 70.5 (3) |
H2A—N2—H2B | 120.0 | C11—C15—Fe1 | 70.2 (3) |
N2—C1—N1 | 116.0 (3) | C14—C15—H15 | 126.0 |
N2—C1—C2 | 122.2 (3) | C11—C15—H15 | 126.0 |
N1—C1—C2 | 121.8 (3) | Fe1—C15—H15 | 125.0 |
C3—C2—C1 | 119.8 (3) | N3—C16—C2 | 175.2 (4) |
C3—C2—C16 | 122.6 (3) | C18—C17—C22 | 117.9 (3) |
C1—C2—C16 | 117.6 (3) | C18—C17—C3 | 121.7 (3) |
C4—C3—C2 | 117.2 (3) | C22—C17—C3 | 120.4 (3) |
C4—C3—C17 | 120.7 (3) | C17—C18—C19 | 121.7 (4) |
C2—C3—C17 | 122.0 (3) | C17—C18—H18 | 119.2 |
C3—C4—C5 | 119.9 (3) | C19—C18—H18 | 119.2 |
C3—C4—H4 | 120.0 | C20—C19—C18 | 119.2 (4) |
C5—C4—H4 | 120.0 | C20—C19—H19 | 120.4 |
N1—C5—C4 | 123.1 (3) | C18—C19—H19 | 120.4 |
N1—C5—C6 | 115.2 (3) | C19—C20—C21 | 120.7 (4) |
C4—C5—C6 | 121.7 (3) | C19—C20—Cl1 | 120.0 (3) |
C10—C6—C7 | 107.0 (3) | C21—C20—Cl1 | 119.3 (3) |
C10—C6—C5 | 125.2 (3) | C20—C21—C22 | 119.5 (4) |
C7—C6—C5 | 127.8 (3) | C20—C21—H21 | 120.3 |
C10—C6—Fe1 | 68.9 (2) | C22—C21—H21 | 120.3 |
C7—C6—Fe1 | 69.73 (19) | C21—C22—C17 | 121.0 (4) |
C5—C6—Fe1 | 124.7 (2) | C21—C22—H22 | 119.5 |
C8—C7—C6 | 108.4 (3) | C17—C22—H22 | 119.5 |
C8—C7—Fe1 | 70.2 (2) | ||
C5—N1—C1—N2 | −178.8 (3) | C13—Fe1—C10—C9 | −52.3 (5) |
C5—N1—C1—C2 | 2.2 (5) | C8—Fe1—C10—C9 | 37.1 (2) |
N2—C1—C2—C3 | −179.8 (3) | C15—Fe1—C10—C6 | 119.0 (2) |
N1—C1—C2—C3 | −0.9 (5) | C14—Fe1—C10—C6 | 159.6 (2) |
N2—C1—C2—C16 | 0.9 (5) | C11—Fe1—C10—C6 | 78.3 (3) |
N1—C1—C2—C16 | 179.8 (3) | C9—Fe1—C10—C6 | −119.1 (3) |
C1—C2—C3—C4 | −1.4 (5) | C7—Fe1—C10—C6 | −38.3 (2) |
C16—C2—C3—C4 | 177.8 (3) | C12—Fe1—C10—C6 | 51.3 (6) |
C1—C2—C3—C17 | 175.5 (3) | C13—Fe1—C10—C6 | −171.4 (4) |
C16—C2—C3—C17 | −5.3 (5) | C8—Fe1—C10—C6 | −81.9 (2) |
C2—C3—C4—C5 | 2.3 (5) | C10—Fe1—C11—C15 | 74.5 (3) |
C17—C3—C4—C5 | −174.6 (3) | C14—Fe1—C11—C15 | −37.6 (3) |
C1—N1—C5—C4 | −1.3 (5) | C6—Fe1—C11—C15 | 117.0 (3) |
C1—N1—C5—C6 | −179.9 (3) | C9—Fe1—C11—C15 | 41.7 (6) |
C3—C4—C5—N1 | −1.1 (5) | C7—Fe1—C11—C15 | 159.3 (3) |
C3—C4—C5—C6 | 177.5 (3) | C12—Fe1—C11—C15 | −118.8 (4) |
N1—C5—C6—C10 | 10.9 (5) | C13—Fe1—C11—C15 | −81.0 (3) |
C4—C5—C6—C10 | −167.8 (3) | C8—Fe1—C11—C15 | −167.5 (4) |
N1—C5—C6—C7 | −166.7 (3) | C15—Fe1—C11—C12 | 118.8 (4) |
C4—C5—C6—C7 | 14.6 (6) | C10—Fe1—C11—C12 | −166.7 (3) |
N1—C5—C6—Fe1 | −76.5 (4) | C14—Fe1—C11—C12 | 81.2 (3) |
C4—C5—C6—Fe1 | 104.9 (4) | C6—Fe1—C11—C12 | −124.2 (3) |
C15—Fe1—C6—C10 | −78.2 (3) | C9—Fe1—C11—C12 | 160.5 (4) |
C14—Fe1—C6—C10 | −46.9 (5) | C7—Fe1—C11—C12 | −81.9 (3) |
C11—Fe1—C6—C10 | −120.5 (2) | C13—Fe1—C11—C12 | 37.8 (3) |
C9—Fe1—C6—C10 | 37.6 (2) | C8—Fe1—C11—C12 | −48.6 (6) |
C7—Fe1—C6—C10 | 118.5 (3) | C15—C11—C12—C13 | −0.8 (5) |
C12—Fe1—C6—C10 | −161.7 (2) | Fe1—C11—C12—C13 | −59.9 (3) |
C13—Fe1—C6—C10 | 168.2 (5) | C15—C11—C12—Fe1 | 59.1 (3) |
C8—Fe1—C6—C10 | 81.2 (2) | C15—Fe1—C12—C13 | 80.8 (3) |
C15—Fe1—C6—C7 | 163.4 (2) | C10—Fe1—C12—C13 | 154.6 (5) |
C10—Fe1—C6—C7 | −118.5 (3) | C14—Fe1—C12—C13 | 37.4 (3) |
C14—Fe1—C6—C7 | −165.4 (4) | C6—Fe1—C12—C13 | −166.5 (3) |
C11—Fe1—C6—C7 | 121.0 (3) | C11—Fe1—C12—C13 | 118.7 (4) |
C9—Fe1—C6—C7 | −80.9 (2) | C9—Fe1—C12—C13 | −42.5 (6) |
C12—Fe1—C6—C7 | 79.9 (3) | C7—Fe1—C12—C13 | −123.0 (3) |
C13—Fe1—C6—C7 | 49.8 (6) | C8—Fe1—C12—C13 | −80.0 (3) |
C8—Fe1—C6—C7 | −37.3 (2) | C15—Fe1—C12—C11 | −37.9 (3) |
C15—Fe1—C6—C5 | 40.8 (4) | C10—Fe1—C12—C11 | 35.9 (7) |
C10—Fe1—C6—C5 | 118.9 (4) | C14—Fe1—C12—C11 | −81.3 (3) |
C14—Fe1—C6—C5 | 72.1 (5) | C6—Fe1—C12—C11 | 74.8 (3) |
C11—Fe1—C6—C5 | −1.6 (4) | C9—Fe1—C12—C11 | −161.2 (4) |
C9—Fe1—C6—C5 | 156.5 (3) | C7—Fe1—C12—C11 | 118.3 (3) |
C7—Fe1—C6—C5 | −122.6 (4) | C13—Fe1—C12—C11 | −118.7 (4) |
C12—Fe1—C6—C5 | −42.7 (4) | C8—Fe1—C12—C11 | 161.3 (3) |
C13—Fe1—C6—C5 | −72.8 (6) | C11—C12—C13—C14 | 0.4 (5) |
C8—Fe1—C6—C5 | −159.8 (3) | Fe1—C12—C13—C14 | −59.1 (3) |
C10—C6—C7—C8 | 0.4 (4) | C11—C12—C13—Fe1 | 59.5 (3) |
C5—C6—C7—C8 | 178.3 (3) | C15—Fe1—C13—C14 | 36.9 (3) |
Fe1—C6—C7—C8 | 59.5 (3) | C10—Fe1—C13—C14 | −40.8 (6) |
C10—C6—C7—Fe1 | −59.1 (2) | C6—Fe1—C13—C14 | 158.3 (5) |
C5—C6—C7—Fe1 | 118.8 (4) | C11—Fe1—C13—C14 | 81.0 (3) |
C15—Fe1—C7—C8 | −160.1 (4) | C9—Fe1—C13—C14 | −78.2 (3) |
C10—Fe1—C7—C8 | −81.3 (2) | C7—Fe1—C13—C14 | −163.3 (3) |
C14—Fe1—C7—C8 | 41.0 (6) | C12—Fe1—C13—C14 | 119.0 (4) |
C6—Fe1—C7—C8 | −119.7 (3) | C8—Fe1—C13—C14 | −121.2 (3) |
C11—Fe1—C7—C8 | 162.5 (2) | C15—Fe1—C13—C12 | −82.1 (3) |
C9—Fe1—C7—C8 | −37.6 (2) | C10—Fe1—C13—C12 | −159.8 (4) |
C12—Fe1—C7—C8 | 119.2 (2) | C14—Fe1—C13—C12 | −119.0 (4) |
C13—Fe1—C7—C8 | 76.9 (3) | C6—Fe1—C13—C12 | 39.3 (7) |
C15—Fe1—C7—C6 | −40.4 (5) | C11—Fe1—C13—C12 | −38.1 (3) |
C10—Fe1—C7—C6 | 38.39 (19) | C9—Fe1—C13—C12 | 162.8 (3) |
C14—Fe1—C7—C6 | 160.7 (5) | C7—Fe1—C13—C12 | 77.7 (3) |
C11—Fe1—C7—C6 | −77.8 (3) | C8—Fe1—C13—C12 | 119.8 (3) |
C9—Fe1—C7—C6 | 82.1 (2) | C12—C13—C14—C15 | 0.2 (5) |
C12—Fe1—C7—C6 | −121.1 (2) | Fe1—C13—C14—C15 | −59.0 (3) |
C13—Fe1—C7—C6 | −163.4 (2) | C12—C13—C14—Fe1 | 59.2 (3) |
C8—Fe1—C7—C6 | 119.7 (3) | C10—Fe1—C14—C15 | −77.8 (3) |
C6—C7—C8—C9 | −0.2 (4) | C6—Fe1—C14—C15 | −44.1 (5) |
Fe1—C7—C8—C9 | 58.6 (3) | C11—Fe1—C14—C15 | 38.3 (3) |
C6—C7—C8—Fe1 | −58.8 (2) | C9—Fe1—C14—C15 | −120.1 (3) |
C15—Fe1—C8—C9 | 39.2 (6) | C7—Fe1—C14—C15 | 167.7 (5) |
C10—Fe1—C8—C9 | −37.2 (2) | C12—Fe1—C14—C15 | 82.4 (3) |
C14—Fe1—C8—C9 | 75.2 (3) | C13—Fe1—C14—C15 | 120.2 (4) |
C6—Fe1—C8—C9 | −81.6 (2) | C8—Fe1—C14—C15 | −161.1 (3) |
C11—Fe1—C8—C9 | −164.4 (4) | C15—Fe1—C14—C13 | −120.2 (4) |
C7—Fe1—C8—C9 | −119.3 (3) | C10—Fe1—C14—C13 | 162.0 (3) |
C12—Fe1—C8—C9 | 159.6 (2) | C6—Fe1—C14—C13 | −164.3 (3) |
C13—Fe1—C8—C9 | 117.1 (2) | C11—Fe1—C14—C13 | −82.0 (3) |
C15—Fe1—C8—C7 | 158.6 (5) | C9—Fe1—C14—C13 | 119.7 (3) |
C10—Fe1—C8—C7 | 82.2 (2) | C7—Fe1—C14—C13 | 47.5 (7) |
C14—Fe1—C8—C7 | −165.5 (3) | C12—Fe1—C14—C13 | −37.8 (3) |
C6—Fe1—C8—C7 | 37.8 (2) | C8—Fe1—C14—C13 | 78.6 (3) |
C11—Fe1—C8—C7 | −45.0 (6) | C13—C14—C15—C11 | −0.7 (5) |
C9—Fe1—C8—C7 | 119.3 (3) | Fe1—C14—C15—C11 | −60.4 (3) |
C12—Fe1—C8—C7 | −81.0 (3) | C13—C14—C15—Fe1 | 59.7 (3) |
C13—Fe1—C8—C7 | −123.6 (2) | C12—C11—C15—C14 | 0.9 (5) |
C7—C8—C9—C10 | −0.1 (4) | Fe1—C11—C15—C14 | 60.6 (3) |
Fe1—C8—C9—C10 | 58.7 (3) | C12—C11—C15—Fe1 | −59.6 (3) |
C7—C8—C9—Fe1 | −58.8 (3) | C10—Fe1—C15—C14 | 118.6 (3) |
C15—Fe1—C9—C10 | 75.2 (3) | C6—Fe1—C15—C14 | 160.5 (3) |
C14—Fe1—C9—C10 | 116.3 (3) | C11—Fe1—C15—C14 | −118.5 (4) |
C6—Fe1—C9—C10 | −38.2 (2) | C9—Fe1—C15—C14 | 77.9 (3) |
C11—Fe1—C9—C10 | 44.4 (6) | C7—Fe1—C15—C14 | −169.8 (4) |
C7—Fe1—C9—C10 | −82.5 (2) | C12—Fe1—C15—C14 | −80.6 (3) |
C12—Fe1—C9—C10 | −171.5 (4) | C13—Fe1—C15—C14 | −36.9 (3) |
C13—Fe1—C9—C10 | 157.5 (2) | C8—Fe1—C15—C14 | 48.8 (6) |
C8—Fe1—C9—C10 | −120.1 (3) | C10—Fe1—C15—C11 | −122.9 (3) |
C15—Fe1—C9—C8 | −164.7 (2) | C14—Fe1—C15—C11 | 118.5 (4) |
C10—Fe1—C9—C8 | 120.1 (3) | C6—Fe1—C15—C11 | −80.9 (3) |
C14—Fe1—C9—C8 | −123.5 (2) | C9—Fe1—C15—C11 | −163.6 (3) |
C6—Fe1—C9—C8 | 81.9 (2) | C7—Fe1—C15—C11 | −51.3 (6) |
C11—Fe1—C9—C8 | 164.5 (4) | C12—Fe1—C15—C11 | 37.9 (3) |
C7—Fe1—C9—C8 | 37.6 (2) | C13—Fe1—C15—C11 | 81.7 (3) |
C12—Fe1—C9—C8 | −51.3 (5) | C8—Fe1—C15—C11 | 167.4 (4) |
C13—Fe1—C9—C8 | −82.4 (3) | C4—C3—C17—C18 | 126.9 (4) |
C8—C9—C10—C6 | 0.4 (4) | C2—C3—C17—C18 | −49.8 (5) |
Fe1—C9—C10—C6 | 59.8 (2) | C4—C3—C17—C22 | −51.3 (5) |
C8—C9—C10—Fe1 | −59.4 (3) | C2—C3—C17—C22 | 131.9 (4) |
C7—C6—C10—C9 | −0.5 (4) | C22—C17—C18—C19 | 1.1 (6) |
C5—C6—C10—C9 | −178.5 (3) | C3—C17—C18—C19 | −177.2 (4) |
Fe1—C6—C10—C9 | −60.1 (2) | C17—C18—C19—C20 | −0.2 (6) |
C7—C6—C10—Fe1 | 59.6 (2) | C18—C19—C20—C21 | −1.1 (6) |
C5—C6—C10—Fe1 | −118.4 (3) | C18—C19—C20—Cl1 | 178.5 (3) |
C15—Fe1—C10—C9 | −122.0 (3) | C19—C20—C21—C22 | 1.5 (6) |
C14—Fe1—C10—C9 | −81.3 (3) | Cl1—C20—C21—C22 | −178.0 (3) |
C6—Fe1—C10—C9 | 119.1 (3) | C20—C21—C22—C17 | −0.7 (6) |
C11—Fe1—C10—C9 | −162.6 (3) | C18—C17—C22—C21 | −0.6 (6) |
C7—Fe1—C10—C9 | 80.8 (2) | C3—C17—C22—C21 | 177.7 (3) |
C12—Fe1—C10—C9 | 170.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···N3i | 0.86 | 2.28 | 3.047 (5) | 149 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Fe(C5H5)(C17H11ClN3)] |
Mr | 413.68 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 12.1517 (13), 7.4214 (11), 20.742 (2) |
β (°) | 97.691 (2) |
V (Å3) | 1853.7 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.97 |
Crystal size (mm) | 0.20 × 0.15 × 0.09 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.830, 0.918 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8876, 3260, 2298 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.093, 1.09 |
No. of reflections | 3260 |
No. of parameters | 244 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.44, −0.43 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···N3i | 0.86 | 2.28 | 3.047 (5) | 148.9 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Acknowledgements
The authors thank the National Natural Science Foundation of China (grant No. 20672090) and the Natural Science Foundation of Jiangsu Province (grant No. BK2006033) for financial support.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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 into 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; Desai & Shah, 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. We report herein the crystal structure of the title compound, (I).
In the molecule of (I), (Fig. 1), rings A (N1/C1-C5), B (C17-C22), C (C6-C10) and D (C11-C15) are, of course, planar. The dihedral angles between them are A/B = 51.33 (4)°, A/C = 13.20 (3)°, A/D = 16.32 (4)°, B/C = 46.38 (3)°, B/D= 44.47 (3)° and C/D = 3.28 (4)°. So, rings C and D are nearly paralllel to each other.
In the crystal structure, intermolecular N-H···N hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.