N'-Ferrocenyl-2-hydroxy-benzohydrazide.

The title complex, [Fe(C(5)H(5))(C(13)H(11)N(2)O(3))], was prepared via self-assembly using ferrocenyl hydrazide and ethyl salicylate. The compound is potentially a tridentate ferrocene-based ligand. The conformation of the mol-ecule allows the formation of an intra-molecular N-H⋯O hydrogen bond involving the hydroxyl group. The CONHNHCO unit and the rings bonded to it are nearly coplanar. The crystal structure is stabilized by inter-molecular O-H⋯O(carbon-yl) and N-H⋯O(carbon-yl) hydrogen bonds.

Related literature

For related literature about applications of ferrocene complexes, see: Beer (1992 ▶); Beer & Smith (1997 ▶); Long (1995 ▶); Miller & Epstein (1994 ▶); Nguyen et al. (1999 ▶).

Experimental

Crystal data

[Fe(C5H5)(C13H11N2O3)]

M = 364.18

Monoclinic,

a = 20.680 (3) Å

b = 9.9673 (15) Å

c = 16.941 (3) Å

β = 121.704 (3)°

V = 2970.8 (8) Å3

Z = 8

Mo Kα radiation

μ = 1.03 mm−1

T = 293 (2) K

0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.820, T max = 0.852

7479 measured reflections

2611 independent reflections

1053 reflections with I > 2σ(I)

R int = 0.129

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.086

S = 0.57

2611 reflections

230 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065634/bh2153sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065634/bh2153Isup2.hkl

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

[Fe(C5H5)(C13H11N2O3)]	F000 = 1504
Mr = 364.18	Dx = 1.628 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 397 reflections
a = 20.680 (3) Å	θ = 2.3–28.0º
b = 9.9673 (15) Å	µ = 1.04 mm−1
c = 16.941 (3) Å	T = 293 (2) K
β = 121.704 (3)º	Block, red
V = 2970.8 (8) Å3	0.20 × 0.18 × 0.16 mm
Z = 8

Bruker SMART APEX CCD area-detector diffractometer	2611 independent reflections
Radiation source: fine-focus sealed tube	1053 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.129
T = 293(2) K	θmax = 25.0º
0.3° wide ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −24→18
Tmin = 0.820, Tmax = 0.852	k = −11→11
7479 measured reflections	l = −20→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.02P)2] where P = (Fo2 + 2Fc2)/3
S = 0.57	(Δ/σ)max < 0.001
2611 reflections	Δρmax = 0.48 e Å−3
230 parameters	Δρmin = −0.34 e Å−3
3 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
Fe1	0.94540 (4)	0.77786 (6)	0.86429 (4)	0.03507 (19)
O1	0.83150 (16)	0.4726 (3)	0.79890 (19)	0.0410 (9)
O2	0.92978 (15)	0.2865 (3)	0.63670 (17)	0.0437 (8)
O3	0.75985 (16)	0.1341 (3)	0.6733 (2)	0.0417 (8)
H3B	0.7289 (10)	0.099 (3)	0.683 (2)	0.060 (9)*
N1	0.9235 (2)	0.3971 (3)	0.7765 (2)	0.0308 (10)
H1B	0.9700 (8)	0.387 (4)	0.790 (2)	0.058 (16)*
N2	0.87479 (18)	0.2969 (4)	0.7205 (2)	0.0340 (9)
H2B	0.8365 (9)	0.276 (3)	0.7248 (17)	0.034 (5)*
C1	0.8498 (3)	0.8152 (5)	0.7406 (3)	0.0489 (14)
H1A	0.8151	0.7473	0.6970	0.059*
C2	0.8456 (3)	0.8730 (4)	0.8133 (3)	0.0432 (13)
H2A	0.8071	0.8530	0.8287	0.052*
C3	0.9052 (3)	0.9656 (4)	0.8594 (3)	0.0451 (14)
H3A	0.9161	1.0216	0.9126	0.054*
C4	0.9463 (3)	0.9629 (4)	0.8144 (3)	0.0454 (14)
H4A	0.9919	1.0160	0.8322	0.055*
C5	0.9131 (3)	0.8688 (5)	0.7419 (3)	0.0529 (15)
H5A	0.9302	0.8462	0.6995	0.064*
C6	1.0186 (3)	0.6269 (4)	0.8847 (3)	0.0376 (13)
H6A	1.0360	0.6011	0.8430	0.045*
C7	1.0541 (2)	0.7191 (4)	0.9589 (3)	0.0415 (13)
H7A	1.1002	0.7706	0.9767	0.050*
C8	1.0106 (3)	0.7288 (4)	1.0008 (3)	0.0444 (13)
H8A	1.0216	0.7865	1.0533	0.053*
C9	0.9489 (3)	0.6410 (4)	0.9538 (3)	0.0337 (12)
H9A	0.9093	0.6261	0.9681	0.040*
C10	0.9534 (3)	0.5776 (4)	0.8825 (3)	0.0304 (12)
C11	0.8976 (3)	0.4797 (4)	0.8161 (3)	0.0302 (12)
C12	0.8800 (2)	0.2468 (4)	0.6504 (3)	0.0272 (11)
C13	0.8246 (2)	0.1417 (4)	0.5917 (3)	0.0269 (11)
C14	0.8305 (3)	0.0933 (4)	0.5195 (3)	0.0388 (13)
H14A	0.8674	0.1284	0.5097	0.047*
C15	0.7828 (3)	−0.0064 (4)	0.4615 (3)	0.0490 (15)
H15A	0.7875	−0.0372	0.4129	0.059*
C16	0.7285 (3)	−0.0601 (4)	0.4754 (3)	0.0422 (14)
H16A	0.6968	−0.1283	0.4371	0.051*
C17	0.7214 (2)	−0.0123 (4)	0.5463 (3)	0.0375 (13)
H17A	0.6845	−0.0485	0.5556	0.045*
C18	0.7675 (3)	0.0877 (4)	0.6038 (3)	0.0300 (12)

	U11	U22	U33	U12	U13	U23
Fe1	0.0332 (4)	0.0339 (3)	0.0390 (4)	0.0019 (4)	0.0195 (3)	−0.0003 (4)
O1	0.0258 (18)	0.0442 (19)	0.058 (2)	−0.0049 (17)	0.0251 (17)	−0.0128 (15)
O2	0.0409 (17)	0.061 (2)	0.0440 (17)	−0.0154 (18)	0.0328 (15)	−0.0120 (16)
O3	0.0369 (18)	0.052 (2)	0.0518 (19)	−0.0128 (17)	0.0345 (16)	−0.0080 (16)
N1	0.026 (2)	0.029 (2)	0.043 (2)	0.000 (2)	0.022 (2)	−0.0085 (17)
N2	0.029 (2)	0.038 (2)	0.043 (2)	−0.005 (2)	0.0246 (18)	−0.0056 (19)
C1	0.043 (3)	0.058 (3)	0.031 (3)	0.006 (3)	0.010 (3)	0.001 (2)
C2	0.044 (3)	0.037 (3)	0.056 (3)	0.013 (3)	0.031 (3)	0.010 (2)
C3	0.049 (3)	0.031 (3)	0.059 (3)	−0.007 (3)	0.031 (3)	−0.007 (2)
C4	0.042 (3)	0.036 (3)	0.066 (4)	0.002 (3)	0.034 (3)	0.011 (3)
C5	0.051 (3)	0.069 (4)	0.048 (3)	0.019 (3)	0.032 (3)	0.021 (3)
C6	0.033 (3)	0.044 (3)	0.033 (3)	0.010 (3)	0.016 (2)	−0.003 (2)
C7	0.021 (2)	0.033 (3)	0.048 (3)	0.011 (3)	0.002 (2)	0.005 (3)
C8	0.049 (3)	0.039 (3)	0.040 (3)	0.000 (3)	0.020 (3)	−0.006 (2)
C9	0.039 (3)	0.029 (3)	0.038 (3)	0.002 (2)	0.024 (2)	−0.002 (2)
C10	0.028 (3)	0.027 (2)	0.037 (3)	−0.001 (2)	0.018 (2)	−0.005 (2)
C11	0.033 (3)	0.028 (3)	0.027 (3)	0.001 (3)	0.013 (2)	0.003 (2)
C12	0.024 (2)	0.030 (3)	0.031 (2)	0.005 (2)	0.016 (2)	0.008 (2)
C13	0.025 (3)	0.023 (2)	0.032 (3)	0.000 (2)	0.014 (2)	0.002 (2)
C14	0.038 (3)	0.042 (3)	0.046 (3)	0.000 (3)	0.028 (3)	0.000 (2)
C15	0.052 (4)	0.056 (3)	0.045 (3)	−0.006 (3)	0.030 (3)	−0.014 (3)
C16	0.038 (3)	0.043 (3)	0.044 (3)	−0.017 (3)	0.021 (3)	−0.019 (2)
C17	0.033 (3)	0.040 (3)	0.041 (3)	−0.012 (2)	0.020 (3)	−0.007 (2)
C18	0.034 (3)	0.030 (3)	0.031 (3)	0.005 (2)	0.020 (2)	0.002 (2)

Fe1—C2	2.008 (4)	C3—H3A	0.9800
Fe1—C9	2.013 (4)	C4—C5	1.405 (6)
Fe1—C10	2.014 (4)	C4—H4A	0.9800
Fe1—C1	2.021 (4)	C5—H5A	0.9800
Fe1—C5	2.028 (5)	C6—C7	1.412 (5)
Fe1—C6	2.031 (4)	C6—C10	1.416 (6)
Fe1—C3	2.031 (4)	C6—H6A	0.9800
Fe1—C8	2.031 (4)	C7—C8	1.412 (6)
Fe1—C4	2.033 (4)	C7—H7A	0.9800
Fe1—C7	2.045 (4)	C8—C9	1.400 (5)
O1—C11	1.240 (5)	C8—H8A	0.9800
O2—C12	1.233 (4)	C9—C10	1.410 (5)
O3—C18	1.349 (5)	C9—H9A	0.9800
O3—H3B	0.822 (10)	C10—C11	1.478 (5)
N1—C11	1.340 (5)	C12—C13	1.484 (5)
N1—N2	1.381 (4)	C13—C14	1.379 (6)
N1—H1B	0.871 (10)	C13—C18	1.407 (6)
N2—C12	1.343 (5)	C14—C15	1.381 (5)
N2—H2B	0.860 (10)	C14—H14A	0.9300
C1—C5	1.402 (6)	C15—C16	1.373 (6)
C1—C2	1.404 (6)	C15—H15A	0.9300
C1—H1A	0.9800	C16—C17	1.370 (6)
C2—C3	1.403 (6)	C16—H16A	0.9300
C2—H2A	0.9800	C17—C18	1.369 (5)
C3—C4	1.410 (6)	C17—H17A	0.9300
C2—Fe1—C9	105.43 (18)	C4—C3—H3A	126.6
C2—Fe1—C10	121.17 (19)	Fe1—C3—H3A	126.6
C9—Fe1—C10	41.01 (16)	C5—C4—C3	109.2 (4)
C2—Fe1—C1	40.79 (16)	C5—C4—Fe1	69.5 (3)
C9—Fe1—C1	122.31 (19)	C3—C4—Fe1	69.6 (3)
C10—Fe1—C1	107.34 (18)	C5—C4—H4A	125.4
C2—Fe1—C5	68.7 (2)	C3—C4—H4A	125.4
C9—Fe1—C5	159.32 (19)	Fe1—C4—H4A	125.4
C10—Fe1—C5	123.77 (19)	C1—C5—C4	107.0 (5)
C1—Fe1—C5	40.53 (17)	C1—C5—Fe1	69.5 (3)
C2—Fe1—C6	158.24 (18)	C4—C5—Fe1	70.0 (3)
C9—Fe1—C6	68.96 (18)	C1—C5—H5A	126.5
C10—Fe1—C6	40.98 (16)	C4—C5—H5A	126.5
C1—Fe1—C6	123.23 (18)	Fe1—C5—H5A	126.5
C5—Fe1—C6	108.72 (19)	C7—C6—C10	107.0 (4)
C2—Fe1—C3	40.66 (16)	C7—C6—Fe1	70.3 (2)
C9—Fe1—C3	120.45 (18)	C10—C6—Fe1	68.9 (2)
C10—Fe1—C3	156.7 (2)	C7—C6—H6A	126.5
C1—Fe1—C3	68.42 (18)	C10—C6—H6A	126.5
C5—Fe1—C3	68.83 (19)	Fe1—C6—H6A	126.5
C6—Fe1—C3	160.36 (19)	C8—C7—C6	108.7 (4)
C2—Fe1—C8	121.38 (19)	C8—C7—Fe1	69.2 (2)
C9—Fe1—C8	40.51 (16)	C6—C7—Fe1	69.2 (2)
C10—Fe1—C8	68.62 (17)	C8—C7—H7A	125.6
C1—Fe1—C8	158.0 (2)	C6—C7—H7A	125.6
C5—Fe1—C8	159.5 (2)	Fe1—C7—H7A	125.6
C6—Fe1—C8	68.81 (18)	C9—C8—C7	107.6 (4)
C3—Fe1—C8	106.29 (19)	C9—C8—Fe1	69.0 (2)
C2—Fe1—C4	67.96 (18)	C7—C8—Fe1	70.2 (2)
C9—Fe1—C4	157.47 (19)	C9—C8—H8A	126.2
C10—Fe1—C4	160.9 (2)	C7—C8—H8A	126.2
C1—Fe1—C4	67.63 (19)	Fe1—C8—H8A	126.2
C5—Fe1—C4	40.48 (17)	C8—C9—C10	108.4 (4)
C6—Fe1—C4	125.03 (19)	C8—C9—Fe1	70.5 (2)
C3—Fe1—C4	40.59 (17)	C10—C9—Fe1	69.5 (2)
C8—Fe1—C4	123.09 (19)	C8—C9—H9A	125.8
C2—Fe1—C7	158.59 (19)	C10—C9—H9A	125.8
C9—Fe1—C7	68.03 (18)	Fe1—C9—H9A	125.8
C10—Fe1—C7	68.14 (18)	C9—C10—C6	108.2 (4)
C1—Fe1—C7	159.89 (19)	C9—C10—C11	124.8 (4)
C5—Fe1—C7	124.4 (2)	C6—C10—C11	127.0 (4)
C6—Fe1—C7	40.55 (15)	C9—C10—Fe1	69.5 (2)
C3—Fe1—C7	123.62 (18)	C6—C10—Fe1	70.2 (2)
C8—Fe1—C7	40.54 (16)	C11—C10—Fe1	124.7 (3)
C4—Fe1—C7	109.83 (19)	O1—C11—N1	121.9 (4)
C18—O3—H3B	120 (3)	O1—C11—C10	122.7 (4)
C11—N1—N2	116.7 (4)	N1—C11—C10	115.3 (4)
C11—N1—H1B	128 (2)	O2—C12—N2	120.7 (4)
N2—N1—H1B	114 (2)	O2—C12—C13	121.8 (4)
C12—N2—N1	120.5 (3)	N2—C12—C13	117.6 (4)
C12—N2—H2B	119 (2)	C14—C13—C18	117.9 (4)
N1—N2—H2B	120 (2)	C14—C13—C12	116.4 (4)
C5—C1—C2	108.5 (4)	C18—C13—C12	125.7 (4)
C5—C1—Fe1	70.0 (3)	C13—C14—C15	121.4 (5)
C2—C1—Fe1	69.1 (3)	C13—C14—H14A	119.3
C5—C1—H1A	125.7	C15—C14—H14A	119.3
C2—C1—H1A	125.7	C16—C15—C14	120.1 (5)
Fe1—C1—H1A	125.7	C16—C15—H15A	120.0
C3—C2—C1	108.5 (4)	C14—C15—H15A	120.0
C3—C2—Fe1	70.6 (3)	C17—C16—C15	119.3 (4)
C1—C2—Fe1	70.1 (3)	C17—C16—H16A	120.3
C3—C2—H2A	125.8	C15—C16—H16A	120.3
C1—C2—H2A	125.8	C18—C17—C16	121.4 (4)
Fe1—C2—H2A	125.8	C18—C17—H17A	119.3
C2—C3—C4	106.8 (4)	C16—C17—H17A	119.3
C2—C3—Fe1	68.8 (2)	O3—C18—C17	120.8 (4)
C4—C3—Fe1	69.8 (3)	O3—C18—C13	119.2 (4)
C2—C3—H3A	126.6	C17—C18—C13	120.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O3	0.860 (10)	1.95 (2)	2.631 (4)	135 (3)
O3—H3B···O1i	0.822 (10)	1.908 (15)	2.705 (4)	163 (4)
N1—H1B···O2ii	0.871 (10)	2.03 (2)	2.810 (4)	148 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O3	0.860 (10)	1.95 (2)	2.631 (4)	135 (3)
O3—H3B⋯O1i	0.822 (10)	1.908 (15)	2.705 (4)	163 (4)
N1—H1B⋯O2ii	0.871 (10)	2.03 (2)	2.810 (4)	148 (4)

Symmetry codes: (i) ; (ii) .