1-Acetyl-3-ferrocenyl-5-methyl-1H-pyrazole and 1-acetyl-5-ferrocenyl-3-(2-pyrid­yl)-1H-pyrazole

Mol­ecules of 1-acetyl-3-ferrocenyl-5-methyl-1H-pyrazole, [Fe(C₅H₅)(C₁₁H₁₁N₂O)], form a centrosymmetric dimer generated by a combination of one C-H...[pi](pyrazole) and one C-H...[pi](cyclo­penta­dienyl) inter­action. The dimers are linked by C-H...[pi] inter­actions, involving the pyrazole rings as acceptors, into layers parallel to (10). Mol­ecules of 1-acetyl-5-ferrocenyl-3-(2-pyrid­yl)-1H-pyrazole, [Fe(C₅H₅)(C₁₅H₁₂N₃O)], are linked by C-H...O inter­actions into a chain running in the [010] direction. Two chains of this type passing through each unit cell are connected by O...[pi](pyridyl) inter­actions into an [010] double chain.

S1. Comment

Recently pyrazole-based compounds have attracted much attention because their set of donor atoms, N₃ and N₂E (E = O and S), are used as important ligands to model the active sites of metalloenzymes and to recogize metal ions (Gross & Vahrenkamp, 2005; Scarpellini et al., 2005; Miranda et al., 2005). Some of their complexes can be used as catalysts and potential drugs (Ajellal et al., 2006; Porchia et al., 2005).

Acylation of tautomeric 3(5)-ferrocenyl-5(3)-methyl-1H-pyrazole with acetyl chloride afforded the first title compound, (I) (Shi et al., 2006) while 5(3)-ferrocenyl-3(5)-(2-pyridyl)-1H-pyrazole synthesized in our group after acylation of the pyrazolyl NH group generated the second title compound, (II). Since 3-(2-pyridyl)-1H-pyrazole acts as a multifunctional ligand having several coordination modes (Hu et al., 2006) and exhibiting plentiful coordination chemistry from dinuclearity to multinuclearity (Lam et al., 1997), compound (II) is expected to afford an interesting coordination chemistry via the set of N₂O donor atoms, viz. one pyridyl N atom, one pyrazolyl N atom and one carbonyl O atom, whereas (I) can act as an NO bidentate organometallic ligand on coordination to a metal ion. In view of the redox activity and nonlinear optical property of the ferrocenyl group, compounds (I) and (II) are also expected to have potential uses as new materials. For the fully unequivocal characterization, crystal structures of title compounds have been determined (Figs. 1 and 2).

As in N,N'-butanedioylbis(5-ferrocenyl-3-methyl-1H-pyrazole), the bond lengths of each pyrazole ring in (I) and (II) indicate electron delocalization (Shi et al., 2005; Tables 1 and 3). The dihedral angles between the pyrazole ring and, respectively, the corresponding substituted cyclopentadienyl ring and the corresponding acetyl plane are 21.52 (11) and 2.9 (3)° for (I), and 28.7 (2) and 9.7 (4)° for (II). Furthermore, for (II), the pyrazole ring and the pyridine ring make a dihedral angle of 4.47 (18)°. As expected, the small dihedral angle of 0.65 (13)° for (I) and 1.4 (2)° for (II) between the unsubstituted cyclopentadienyl ring and the substituted cyclopentadienyl ring indicates that the two cyclopentadienyl rings are parallel to each other. The C3–Cg2–Cg3–C10 torsion angle of 6.43 (15)° for (I) and 5.6 (3)° for (II), where Cg2 and Cg3 are the centroids of rings C1–C5 and C6–C10, indicates that the two cyclopentadienyl rings of the ferrocenyl group in each of (I) and (II) are nearly in an eclipsed conformation, as was previously observed in a ferrocene-containing compound (Erasmus et al., 1996).

Interestingly, the above dihedral angles and the C10—C11 bond lengths for (I) and C10—C11 and C13—C14 bond lengths for (II) (which are shorter than the value of 1.48 Å for a Csp²—Csp² single bond) suggest that each pyrazole ring of (I) and (II) is slightly conjugated with the corresponding substituted cyclopentadienyl ring and the pyridine ring (Tables 1 and 3).

Although compounds (I) and (II) both crystallize in space group P2₁/n, their packing modes are different. Since the pyrazole ring electrons are delocalized, an intermolecular three-center C—H···(N)₂ hydrogen bond indicates that there exists a C—H···π interaction involving the pyrazole ring in the crystalline state of (I) (Glidewell et al., 2005; Sylvestre et al., 2005; Table 3). Atoms C2 and C16 in the molecule at (x, y, z) act as hydrogen-bond donors, via atoms H2 and H16B, to the pyrazole ring N1/N2/C11–C13 and the unsubstituted cyclopentadienyl ring C1–C5 in the corresponding molecule at (1 − x, 1 − y, 1 − z), so leading to the formation of a centrosymmetric dimer (Fig. 3). The dimer is linked into a [010] double chain with the 2₁ screw axis along (3/4, y, 3/4) by hydrogen bonds in which atom C9 in the substituted cyclopentadienyl ring of the molecule at (x, y, z) acts as a hydrogen-bond donor, via atom H9, to the pyrazole ring N1/N2/C11–C13 in the corresponding molecule at (3/2 − x, −1/2 + y, 3/2 − z), and the pyrazole ring in the molecule at (x, y, z) acts as a hydrogen-bond acceptor and atom C9 in the corresponding molecule at (3/2 − x, 1/2 + y, 3/2 − z) as a hydrogen-bond donor.

In contrast, intermolecular C—H···O interactions are present in the crystalline state of (II) and the N atoms in (II) do not participate in hydrogen-bond formation (Table 4). Atom C8 in the substituted cyclopentadienyl ring of the molecule at (x, y, z) acts as a hydrogen-bond donor, via atom H8, to atom O1 in the corresponding molecule at (3/2 − x, 1/2 + y, 3/2 − z), and atom O1 in the molecule at (x, y, z) acts in turn as a hydrogen-bond acceptor and atom C8 in the corresponding molecule at (3/2 − x, −1/2 + y, 3/2 − z) as a hydrogen-bond donor (Fig. 4). Via the intermolecular C—H···O hydrogen bonds, molecules of (II) form a [010] chain and generate a 2₁ screw axis along (3/4, y, 3/4). Two chains of this type through each unit cell are linked by O···π contact interactions (Jara et al., 2006; Spek, 2003) into a [010] double chain [O1···Cg4ⁱ = 3.913 (3) Å, C19···Cg4ⁱ = 3.864 (3) Å and C19—O1···Cg4ⁱ = 78.9 (2)°; symmetry code: (i) 1 − x, 1 − y, 1 − z; Cg4 is the centroid of ring N3/C14–C18].

S2. Experimental

To a solution of 3(5)-ferrocenyl-5(3)-methyl-1H-pyrazole (1.33 g, 5 mmol) and Et₃N (1.423 g, 14 mmol) in 10 ml of THF was added dropwise acetyl chloride (1 ml, 14 mmol) in 5 ml of THF at ambient temperature. The reaction mixture was stirred for 1 h. After removal of the solvent, the resulting solid was washed with water, air-dried and recrystallized from dichloromethane and petroleum ether to afford the orange title compound (I) (yield 62.2%; m.p. 440.15–441.15 K). Analysis calculated for C₁₆H₁₆FeN₂O: C 62.36, H 5.23, N 9.09%; found: C 62.15, H 5.28, N 9.32%. IR (KBr, cm⁻¹): 1721 (vs, O═C). UV (λ_max, in DMF, nm): 256.00 (2.68 × 10⁴, B band), 328.00 (0.05 × 10⁴, R band). ¹H NMR (CDCl₃, p.p.m.): δ 6.200 (1H, s, CH), 4.694, 4.332 (s, 2H, s, 2H, C₅H₄), 4.102 (s, 5H, C₅H₅), 2.704 (s, 3H, COCH₃), 2.603 (s, 3H, CH₃). The similar reaction of 5(3)-ferrocenyl-3(5)-(2-pyridinyl)-1H-pyrazole (1.646 g, 5 mmol), acetyl chloride (2 ml, 28 mmol) and Et₃N (3.036 g, 30 mmol), via chromatography on silica gel with dichloromethane as an eluant, gave the red title compound (II) (yield 47.2%; m.p. 423.65–424.45 K). Analysis calculated for C₂₀H₁₇FeN₃O: C 64.71, H 4.62, N 11.32%; found: C 64.71, H 4.57, N 11.46%. IR (KBr, cm⁻¹): 1724 (vs, CO). UV (λ_max, in DMF, nm): 278.00 (2.32 × 10⁴, B band), 374.00 (0.1 × 10⁴, K band), 451.00 (0.046 × 10⁴, d–d band). ¹H NMR (600 MHz, CDCl₃, p.p.m.): δ 8.703–8.699, 8.123–8.110, 7.810–7.784, 7.329–7.309 (d, 1H, d, 1H, t, 1H, q, 1H, C₅H₄N), 7.200 (s, 1H, CH), 4.745, 4.364 (s, 2H, s, 2H, C₅H₄), 4.170 (s, 5H, C₅H₅), 2.809 (s, 3H, CH₃).

S3. Refinement

All H atoms bonded to parent atoms were located in difference maps and were treated as riding atoms, with C—H distances of 0.95 Å (pyrazolyl CH), 0.98 Å (CH₃) and 1.00 Å (Cp CH) at 193 K for (I), and C—H distances of 0.93–0.96 Å at 295 K for (II), and with U_iso(H) values of 1.2U_eq(C), or 1.5U_eq(C) for the methyl group(s). The H atoms of the C20 methyl group in (II) were modelled as six equally spaced half H atoms.

Computing details

Data collection: CrystalClear (Rigaku, 2001) for (I); CAD-4 Software (Enraf–Nonius, 1989) for (II). Cell refinement: CrystalClear for (I); CAD-4 Software for (II). Data reduction: CrystalStructure (Rigaku, 2001) for (I); XCAD4 (Harms & Wocadlo, 1995) for (II). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The molecular structure of (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 3. Part of the crystal structure of (I), showing the formation of a [010] chain. Atoms marked with an asterisk (*), hash (#) or dollar sign ($) are at the symmetry positions (3/2 − x, −1/2 + y, 3/2 − z), (1 − x, 1 − y, 1 − z) and (−3/2 + x, 1/2 − y, −3/2 + z), respectively. For clarity, H atoms not involved in the motifs shown have been omitted.
	Fig. 4. Part of the crystal structure of (II), showing the formation of a [010] chain. Atoms marked with an asterisk (*), hash (#), dollar sign ($) or ampersand (&) are at the symmetry positions (3/2 − x, 1/2 + y, 3/2 − z), (3/2 − x, −1/2 + y, 3/2 − z), (1 − x, 1 − y, 1 − z) and (−3/2 + x, 1/2 − y, −3/2 + z), respectively. For clarity, H atoms not involved in the motifs shown have been omitted.

(I) 1-Acetyl-3-ferrocenyl-5-methyl-1H-pyrazole

Crystal data

[Fe(C5H5)(C11H11N2O)]	F(000) = 640
Mr = 308.16	Dx = 1.477 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 5863 reflections
a = 11.8781 (18) Å	θ = 3.1–27.5°
b = 7.2993 (10) Å	µ = 1.08 mm^−1
c = 16.088 (2) Å	T = 193 K
β = 96.353 (5)°	Block, orange
V = 1386.3 (3) Å^3	0.50 × 0.35 × 0.16 mm
Z = 4

Data collection

Rigaku Mercury diffractometer	3178 independent reflections
Radiation source: fine-focus sealed tube	2964 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 7.31 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −15→14
Absorption correction: multi-scan (Jacobson, 1998)	k = −9→9
Tmin = 0.613, Tmax = 0.846	l = −20→20
14815 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0322P)^2 + 0.841P] where P = (Fo^2 + 2Fc^2)/3
3178 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.76919 (2)	0.46668 (3)	0.539625 (15)	0.02227 (9)
O1	0.33436 (12)	0.8684 (2)	0.77219 (10)	0.0458 (4)
N1	0.49087 (12)	0.7683 (2)	0.71718 (9)	0.0258 (3)
N2	0.57258 (12)	0.8046 (2)	0.66449 (9)	0.0251 (3)
C16	0.40302 (19)	1.0581 (3)	0.66757 (16)	0.0431 (5)
H16A	0.3360	1.1332	0.6736	0.065*
H16B	0.4014	1.0175	0.6094	0.065*
H16C	0.4716	1.1306	0.6830	0.065*
C15	0.40317 (16)	0.8953 (3)	0.72333 (13)	0.0330 (4)
C14	0.43764 (19)	0.5238 (3)	0.81953 (14)	0.0418 (5)
H14A	0.4721	0.4107	0.8433	0.063*
H14B	0.3631	0.4963	0.7897	0.063*
H14C	0.4291	0.6112	0.8646	0.063*
C13	0.51180 (15)	0.6049 (3)	0.76014 (11)	0.0279 (4)
C12	0.60871 (16)	0.5371 (3)	0.73392 (11)	0.0280 (4)
H12	0.6461	0.4265	0.7517	0.034*
C11	0.64284 (14)	0.6641 (2)	0.67475 (10)	0.0238 (3)
C10	0.74240 (15)	0.6537 (2)	0.62975 (10)	0.0243 (3)
C9	0.84107 (15)	0.5459 (3)	0.65479 (12)	0.0293 (4)
H9	0.8530	0.4664	0.7056	0.035*
C8	0.91870 (16)	0.5703 (3)	0.59469 (13)	0.0357 (5)
H8	0.9948	0.5111	0.5957	0.043*
C7	0.86901 (18)	0.6922 (3)	0.53264 (13)	0.0363 (5)
H7	0.9040	0.7333	0.4821	0.044*
C6	0.76016 (17)	0.7435 (2)	0.55352 (12)	0.0301 (4)
H6	0.7057	0.8275	0.5206	0.036*
C5	0.79989 (19)	0.2131 (3)	0.49373 (15)	0.0431 (5)
H5	0.8739	0.1466	0.5008	0.052*
C4	0.7141 (2)	0.2041 (3)	0.54861 (15)	0.0477 (6)
H4	0.7168	0.1298	0.6010	0.057*
C3	0.62432 (19)	0.3174 (3)	0.51574 (15)	0.0459 (6)
H3	0.5521	0.3384	0.5409	0.055*
C2	0.65368 (19)	0.3968 (3)	0.44176 (14)	0.0442 (5)
H2	0.6060	0.4841	0.4052	0.053*
C1	0.76194 (19)	0.3326 (3)	0.42772 (13)	0.0407 (5)
H1	0.8044	0.3663	0.3796	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.02582 (14)	0.01771 (14)	0.02343 (14)	−0.00012 (9)	0.00350 (10)	−0.00205 (9)
O1	0.0358 (8)	0.0518 (10)	0.0520 (9)	0.0084 (7)	0.0150 (7)	−0.0079 (8)
N1	0.0238 (7)	0.0278 (8)	0.0255 (7)	0.0013 (6)	0.0014 (6)	−0.0055 (6)
N2	0.0259 (7)	0.0252 (7)	0.0239 (7)	0.0003 (6)	0.0017 (6)	−0.0045 (6)
C16	0.0367 (11)	0.0350 (11)	0.0572 (14)	0.0117 (9)	0.0034 (10)	−0.0012 (10)
C15	0.0265 (9)	0.0345 (10)	0.0370 (10)	0.0031 (8)	−0.0015 (8)	−0.0122 (8)
C14	0.0413 (12)	0.0478 (13)	0.0386 (11)	0.0015 (10)	0.0148 (9)	0.0052 (10)
C13	0.0292 (9)	0.0316 (10)	0.0223 (8)	−0.0009 (8)	0.0000 (7)	−0.0027 (7)
C12	0.0300 (9)	0.0284 (9)	0.0253 (9)	0.0038 (7)	0.0010 (7)	0.0014 (7)
C11	0.0263 (8)	0.0231 (8)	0.0212 (8)	0.0007 (7)	−0.0011 (6)	−0.0052 (7)
C10	0.0272 (8)	0.0216 (8)	0.0234 (8)	−0.0001 (7)	0.0003 (6)	−0.0043 (7)
C9	0.0260 (9)	0.0360 (10)	0.0251 (9)	0.0031 (8)	−0.0009 (7)	−0.0045 (7)
C8	0.0226 (9)	0.0427 (11)	0.0424 (11)	−0.0043 (8)	0.0056 (8)	−0.0111 (9)
C7	0.0429 (11)	0.0297 (10)	0.0392 (11)	−0.0110 (9)	0.0171 (9)	−0.0050 (8)
C6	0.0420 (11)	0.0159 (8)	0.0327 (9)	−0.0018 (7)	0.0051 (8)	−0.0005 (7)
C5	0.0458 (12)	0.0258 (10)	0.0583 (14)	0.0052 (9)	0.0087 (10)	−0.0168 (10)
C4	0.0772 (17)	0.0209 (9)	0.0470 (13)	−0.0139 (11)	0.0165 (12)	−0.0036 (9)
C3	0.0376 (11)	0.0403 (12)	0.0627 (15)	−0.0174 (10)	0.0179 (10)	−0.0252 (11)
C2	0.0457 (12)	0.0409 (12)	0.0423 (12)	−0.0007 (10)	−0.0119 (10)	−0.0164 (10)
C1	0.0508 (12)	0.0390 (11)	0.0340 (10)	−0.0124 (10)	0.0124 (9)	−0.0168 (9)

Geometric parameters (Å, º)

Fe1—C1	2.0424 (19)	C15—C16	1.489 (3)
Fe1—C2	2.036 (2)	C16—H16A	0.9800
Fe1—C3	2.037 (2)	C16—H16B	0.9800
Fe1—C4	2.036 (2)	C16—H16C	0.9800
Fe1—C5	2.040 (2)	C10—C6	1.427 (3)
Fe1—C6	2.0374 (18)	C10—C9	1.432 (3)
Fe1—C7	2.0390 (19)	C9—H9	1.0000
Fe1—C8	2.0402 (19)	C8—C9	1.419 (3)
Fe1—C9	2.0363 (18)	C7—C8	1.416 (3)
Fe1—C10	2.0421 (17)	C8—H8	1.0000
O1—C15	1.211 (2)	C7—H7	1.0000
N1—N2	1.383 (2)	C6—C7	1.422 (3)
N1—C13	1.387 (2)	C6—H6	1.0000
N1—C15	1.406 (2)	C1—C5	1.409 (3)
C11—N2	1.321 (2)	C5—C4	1.422 (3)
C10—C11	1.455 (2)	C5—H5	1.0000
C11—C12	1.420 (3)	C4—H4	1.0000
C12—C13	1.362 (3)	C3—C4	1.405 (4)
C12—H12	0.9500	C3—C2	1.402 (3)
C13—C14	1.492 (3)	C3—H3	1.0000
C14—H14A	0.9800	C2—C1	1.410 (3)
C14—H14B	0.9800	C2—H2	1.0000
C14—H14C	0.9800	C1—H1	1.0000
C2—Fe1—C4	67.94 (10)	C6—C10—C9	107.45 (16)
C2—Fe1—C9	162.52 (9)	C6—C10—C11	127.54 (16)
C4—Fe1—C9	107.98 (9)	C9—C10—C11	125.00 (16)
C2—Fe1—C3	40.27 (10)	C6—C10—Fe1	69.35 (10)
C4—Fe1—C3	40.37 (10)	C9—C10—Fe1	69.23 (10)
C9—Fe1—C3	125.73 (9)	C11—C10—Fe1	125.95 (12)
C2—Fe1—C6	107.11 (9)	C7—C6—C10	107.87 (17)
C4—Fe1—C6	154.80 (9)	C7—C6—Fe1	69.65 (11)
C9—Fe1—C6	68.91 (8)	C10—C6—Fe1	69.71 (10)
C3—Fe1—C6	119.84 (9)	C7—C6—H6	126.1
C2—Fe1—C7	120.39 (10)	C10—C6—H6	126.1
C4—Fe1—C7	163.26 (10)	Fe1—C6—H6	126.1
C9—Fe1—C7	68.47 (8)	C8—C7—C6	108.54 (17)
C3—Fe1—C7	154.90 (10)	C8—C7—Fe1	69.73 (11)
C6—Fe1—C7	40.82 (8)	C6—C7—Fe1	69.53 (11)
C2—Fe1—C8	155.31 (10)	C8—C7—H7	125.7
C4—Fe1—C8	126.13 (10)	C6—C7—H7	125.7
C9—Fe1—C8	40.75 (8)	Fe1—C7—H7	125.7
C3—Fe1—C8	163.09 (10)	C7—C8—C9	107.91 (17)
C6—Fe1—C8	68.80 (8)	C7—C8—Fe1	69.64 (11)
C7—Fe1—C8	40.63 (9)	C9—C8—Fe1	69.48 (11)
C2—Fe1—C5	67.98 (9)	C7—C8—H8	126.0
C4—Fe1—C5	40.84 (9)	C9—C8—H8	126.0
C9—Fe1—C5	120.88 (9)	Fe1—C8—H8	126.0
C3—Fe1—C5	68.14 (9)	C8—C9—C10	108.23 (17)
C6—Fe1—C5	162.40 (9)	C8—C9—Fe1	69.77 (11)
C7—Fe1—C5	125.74 (9)	C10—C9—Fe1	69.66 (10)
C8—Fe1—C5	108.16 (9)	C8—C9—H9	125.9
C2—Fe1—C10	124.89 (8)	C10—C9—H9	125.9
C4—Fe1—C10	120.16 (8)	Fe1—C9—H9	125.9
C9—Fe1—C10	41.11 (7)	C2—C3—C4	108.2 (2)
C3—Fe1—C10	107.26 (8)	C2—C3—Fe1	69.81 (12)
C6—Fe1—C10	40.94 (7)	C4—C3—Fe1	69.77 (12)
C7—Fe1—C10	68.69 (7)	C2—C3—H3	125.9
C8—Fe1—C10	68.92 (7)	C4—C3—H3	125.9
C5—Fe1—C10	155.72 (9)	Fe1—C3—H3	125.9
C2—Fe1—C1	40.46 (9)	C3—C2—C1	108.4 (2)
C4—Fe1—C1	68.22 (9)	C3—C2—Fe1	69.92 (12)
C9—Fe1—C1	155.60 (9)	C1—C2—Fe1	70.03 (12)
C3—Fe1—C1	67.98 (9)	C3—C2—H2	125.8
C6—Fe1—C1	125.06 (9)	C1—C2—H2	125.8
C7—Fe1—C1	107.84 (8)	Fe1—C2—H2	125.8
C8—Fe1—C1	120.67 (8)	C5—C1—C2	107.8 (2)
C5—Fe1—C1	40.38 (9)	C5—C1—Fe1	69.73 (12)
C10—Fe1—C1	162.08 (9)	C2—C1—Fe1	69.51 (11)
N2—C11—C10	121.01 (16)	C5—C1—H1	126.1
N2—C11—C12	111.56 (16)	C2—C1—H1	126.1
C10—C11—C12	127.41 (16)	Fe1—C1—H1	126.1
N2—N1—C13	111.77 (14)	C1—C5—C4	107.8 (2)
N2—N1—C15	119.51 (16)	C1—C5—Fe1	69.89 (11)
C13—N1—C15	128.68 (16)	C4—C5—Fe1	69.41 (11)
C11—N2—N1	104.55 (14)	C1—C5—H5	126.1
O1—C15—N1	119.84 (19)	C4—C5—H5	126.1
O1—C15—C16	124.36 (19)	Fe1—C5—H5	126.1
N1—C15—C16	115.80 (18)	C3—C4—C5	107.8 (2)
C11—C12—C13	106.50 (16)	C3—C4—Fe1	69.86 (12)
C13—C12—H12	126.8	C5—C4—Fe1	69.75 (12)
C11—C12—H12	126.8	C3—C4—H4	126.1
N1—C13—C14	125.05 (17)	C5—C4—H4	126.1
C12—C13—N1	105.62 (16)	Fe1—C4—H4	126.1
C12—C13—C14	129.30 (19)	C13—C14—H14A	109.5
C15—C16—H16A	109.5	C13—C14—H14B	109.5
C15—C16—H16B	109.5	H14A—C14—H14B	109.5
H16A—C16—H16B	109.5	C13—C14—H14C	109.5
C15—C16—H16C	109.5	H14A—C14—H14C	109.5
H16A—C16—H16C	109.5	H14B—C14—H14C	109.5
H16B—C16—H16C	109.5
C12—C11—N2—N1	−0.47 (18)	C11—C10—C9—Fe1	120.06 (17)
C10—C11—N2—N1	−179.22 (14)	C2—Fe1—C9—C8	−161.5 (3)
C13—N1—N2—C11	0.28 (18)	C4—Fe1—C9—C8	124.97 (14)
C15—N1—N2—C11	178.32 (15)	C3—Fe1—C9—C8	166.10 (13)
N2—N1—C15—O1	−176.59 (17)	C6—Fe1—C9—C8	−81.60 (13)
C13—N1—C15—O1	1.1 (3)	C7—Fe1—C9—C8	−37.64 (13)
N2—N1—C15—C16	3.0 (2)	C5—Fe1—C9—C8	82.08 (15)
C13—N1—C15—C16	−179.31 (18)	C10—Fe1—C9—C8	−119.47 (17)
N2—C11—C12—C13	0.5 (2)	C1—Fe1—C9—C8	48.2 (3)
C10—C11—C12—C13	179.15 (16)	C2—Fe1—C9—C10	−42.1 (3)
C11—C12—C13—N1	−0.29 (19)	C4—Fe1—C9—C10	−115.56 (12)
C11—C12—C13—C14	177.47 (19)	C3—Fe1—C9—C10	−74.43 (14)
N2—N1—C13—C12	0.01 (19)	C6—Fe1—C9—C10	37.87 (11)
C15—N1—C13—C12	−177.79 (17)	C7—Fe1—C9—C10	81.84 (12)
N2—N1—C13—C14	−177.86 (17)	C8—Fe1—C9—C10	119.47 (17)
C15—N1—C13—C14	4.3 (3)	C5—Fe1—C9—C10	−158.45 (11)
N2—C11—C10—C6	−22.8 (3)	C1—Fe1—C9—C10	167.67 (18)
C12—C11—C10—C6	158.66 (18)	C4—Fe1—C3—C2	−119.41 (19)
N2—C11—C10—C9	158.29 (17)	C9—Fe1—C3—C2	165.60 (12)
C12—C11—C10—C9	−20.2 (3)	C6—Fe1—C3—C2	81.24 (15)
N2—C11—C10—Fe1	−113.26 (17)	C7—Fe1—C3—C2	47.6 (2)
C12—C11—C10—Fe1	68.2 (2)	C8—Fe1—C3—C2	−161.8 (3)
C2—Fe1—C10—C6	−75.14 (14)	C5—Fe1—C3—C2	−81.28 (15)
C4—Fe1—C10—C6	−158.00 (13)	C10—Fe1—C3—C2	124.05 (13)
C9—Fe1—C10—C6	119.06 (16)	C1—Fe1—C3—C2	−37.59 (14)
C3—Fe1—C10—C6	−115.91 (13)	C2—Fe1—C3—C4	119.41 (19)
C7—Fe1—C10—C6	37.82 (11)	C9—Fe1—C3—C4	−74.99 (15)
C8—Fe1—C10—C6	81.55 (12)	C6—Fe1—C3—C4	−159.34 (13)
C5—Fe1—C10—C6	169.12 (19)	C7—Fe1—C3—C4	166.97 (18)
C1—Fe1—C10—C6	−44.3 (3)	C8—Fe1—C3—C4	−42.4 (3)
C2—Fe1—C10—C9	165.80 (13)	C5—Fe1—C3—C4	38.13 (13)
C4—Fe1—C10—C9	82.94 (14)	C10—Fe1—C3—C4	−116.54 (13)
C3—Fe1—C10—C9	125.03 (13)	C1—Fe1—C3—C4	81.82 (14)
C6—Fe1—C10—C9	−119.06 (16)	C4—C3—C2—C1	0.3 (2)
C7—Fe1—C10—C9	−81.24 (12)	Fe1—C3—C2—C1	59.69 (14)
C8—Fe1—C10—C9	−37.52 (12)	C4—C3—C2—Fe1	−59.39 (15)
C5—Fe1—C10—C9	50.1 (2)	C4—Fe1—C2—C3	37.51 (14)
C1—Fe1—C10—C9	−163.3 (2)	C9—Fe1—C2—C3	−42.2 (4)
C2—Fe1—C10—C11	46.94 (19)	C6—Fe1—C2—C3	−116.23 (14)
C4—Fe1—C10—C11	−35.92 (19)	C7—Fe1—C2—C3	−158.72 (13)
C9—Fe1—C10—C11	−118.9 (2)	C8—Fe1—C2—C3	167.42 (19)
C3—Fe1—C10—C11	6.17 (18)	C5—Fe1—C2—C3	81.73 (15)
C6—Fe1—C10—C11	122.1 (2)	C10—Fe1—C2—C3	−74.72 (16)
C7—Fe1—C10—C11	159.89 (17)	C1—Fe1—C2—C3	119.4 (2)
C8—Fe1—C10—C11	−156.38 (17)	C4—Fe1—C2—C1	−81.85 (15)
C5—Fe1—C10—C11	−68.8 (3)	C9—Fe1—C2—C1	−161.6 (3)
C1—Fe1—C10—C11	77.8 (3)	C3—Fe1—C2—C1	−119.4 (2)
C9—C10—C6—C7	−0.5 (2)	C6—Fe1—C2—C1	124.41 (14)
C11—C10—C6—C7	−179.52 (17)	C7—Fe1—C2—C1	81.92 (15)
Fe1—C10—C6—C7	−59.42 (13)	C8—Fe1—C2—C1	48.1 (3)
C9—C10—C6—Fe1	58.95 (12)	C5—Fe1—C2—C1	−37.63 (14)
C11—C10—C6—Fe1	−120.11 (18)	C10—Fe1—C2—C1	165.92 (12)
C2—Fe1—C6—C7	−116.96 (13)	C3—C2—C1—C5	−0.2 (2)
C4—Fe1—C6—C7	168.6 (2)	Fe1—C2—C1—C5	59.42 (14)
C9—Fe1—C6—C7	81.06 (13)	C3—C2—C1—Fe1	−59.62 (14)
C3—Fe1—C6—C7	−158.91 (13)	C2—Fe1—C1—C5	−119.1 (2)
C8—Fe1—C6—C7	37.23 (12)	C4—Fe1—C1—C5	−38.03 (14)
C5—Fe1—C6—C7	−46.0 (3)	C9—Fe1—C1—C5	47.6 (3)
C10—Fe1—C6—C7	119.09 (16)	C3—Fe1—C1—C5	−81.70 (15)
C1—Fe1—C6—C7	−76.12 (15)	C6—Fe1—C1—C5	166.47 (13)
C2—Fe1—C6—C10	123.95 (12)	C7—Fe1—C1—C5	124.66 (14)
C4—Fe1—C6—C10	49.5 (3)	C8—Fe1—C1—C5	82.06 (15)
C9—Fe1—C6—C10	−38.03 (10)	C10—Fe1—C1—C5	−159.6 (2)
C3—Fe1—C6—C10	82.00 (13)	C4—Fe1—C1—C2	81.09 (16)
C7—Fe1—C6—C10	−119.09 (16)	C9—Fe1—C1—C2	166.73 (19)
C8—Fe1—C6—C10	−81.86 (12)	C3—Fe1—C1—C2	37.43 (15)
C5—Fe1—C6—C10	−165.1 (3)	C6—Fe1—C1—C2	−74.41 (16)
C1—Fe1—C6—C10	164.79 (11)	C7—Fe1—C1—C2	−116.22 (15)
C10—C6—C7—C8	0.5 (2)	C8—Fe1—C1—C2	−158.82 (14)
Fe1—C6—C7—C8	−58.98 (14)	C5—Fe1—C1—C2	119.1 (2)
C10—C6—C7—Fe1	59.45 (12)	C10—Fe1—C1—C2	−40.4 (3)
C2—Fe1—C7—C8	−159.06 (12)	C2—C1—C5—C4	0.0 (2)
C4—Fe1—C7—C8	−43.1 (3)	Fe1—C1—C5—C4	59.30 (14)
C9—Fe1—C7—C8	37.74 (11)	C2—C1—C5—Fe1	−59.28 (14)
C3—Fe1—C7—C8	167.36 (18)	C2—Fe1—C5—C1	37.70 (14)
C6—Fe1—C7—C8	119.98 (17)	C4—Fe1—C5—C1	119.0 (2)
C5—Fe1—C7—C8	−75.58 (15)	C9—Fe1—C5—C1	−159.17 (12)
C10—Fe1—C7—C8	82.05 (12)	C3—Fe1—C5—C1	81.27 (15)
C1—Fe1—C7—C8	−116.61 (13)	C6—Fe1—C5—C1	−39.3 (3)
C2—Fe1—C7—C6	80.96 (14)	C7—Fe1—C5—C1	−74.72 (16)
C4—Fe1—C7—C6	−163.1 (3)	C8—Fe1—C5—C1	−116.30 (14)
C9—Fe1—C7—C6	−82.24 (12)	C10—Fe1—C5—C1	164.85 (17)
C3—Fe1—C7—C6	47.4 (2)	C2—Fe1—C5—C4	−81.28 (16)
C8—Fe1—C7—C6	−119.98 (17)	C9—Fe1—C5—C4	81.85 (16)
C5—Fe1—C7—C6	164.44 (12)	C3—Fe1—C5—C4	−37.71 (15)
C10—Fe1—C7—C6	−37.93 (11)	C6—Fe1—C5—C4	−158.3 (3)
C1—Fe1—C7—C6	123.41 (12)	C7—Fe1—C5—C4	166.31 (14)
C6—C7—C8—C9	−0.3 (2)	C8—Fe1—C5—C4	124.72 (15)
Fe1—C7—C8—C9	−59.15 (14)	C10—Fe1—C5—C4	45.9 (3)
C6—C7—C8—Fe1	58.86 (14)	C1—Fe1—C5—C4	−119.0 (2)
C2—Fe1—C8—C7	47.6 (3)	C2—C3—C4—C5	−0.3 (2)
C4—Fe1—C8—C7	165.90 (12)	Fe1—C3—C4—C5	−59.70 (15)
C9—Fe1—C8—C7	−119.28 (17)	C2—C3—C4—Fe1	59.41 (15)
C3—Fe1—C8—C7	−161.4 (3)	C1—C5—C4—C3	0.2 (2)
C6—Fe1—C8—C7	−37.40 (11)	Fe1—C5—C4—C3	59.76 (14)
C5—Fe1—C8—C7	124.18 (13)	C1—C5—C4—Fe1	−59.60 (14)
C10—Fe1—C8—C7	−81.44 (12)	C2—Fe1—C4—C3	−37.42 (13)
C1—Fe1—C8—C7	81.70 (14)	C9—Fe1—C4—C3	124.48 (13)
C2—Fe1—C8—C9	166.84 (19)	C6—Fe1—C4—C3	45.9 (3)
C4—Fe1—C8—C9	−74.82 (15)	C7—Fe1—C4—C3	−160.6 (3)
C3—Fe1—C8—C9	−42.1 (3)	C8—Fe1—C4—C3	165.96 (13)
C6—Fe1—C8—C9	81.88 (12)	C5—Fe1—C4—C3	−118.8 (2)
C7—Fe1—C8—C9	119.28 (17)	C10—Fe1—C4—C3	81.16 (15)
C5—Fe1—C8—C9	−116.54 (13)	C1—Fe1—C4—C3	−81.18 (15)
C10—Fe1—C8—C9	37.84 (11)	C2—Fe1—C4—C5	81.38 (15)
C1—Fe1—C8—C9	−159.02 (12)	C9—Fe1—C4—C5	−116.72 (14)
C7—C8—C9—C10	0.0 (2)	C3—Fe1—C4—C5	118.8 (2)
Fe1—C8—C9—C10	−59.25 (13)	C6—Fe1—C4—C5	164.74 (18)
C7—C8—C9—Fe1	59.25 (14)	C7—Fe1—C4—C5	−41.8 (4)
C6—C10—C9—C8	0.3 (2)	C8—Fe1—C4—C5	−75.25 (16)
C11—C10—C9—C8	179.38 (17)	C10—Fe1—C4—C5	−160.04 (13)
Fe1—C10—C9—C8	59.32 (13)	C1—Fe1—C4—C5	37.62 (14)
C6—C10—C9—Fe1	−59.03 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg1^i	1.00	2.85	3.408 (2)	116
C9—H9···Cg1^ii	1.00	2.64	3.567 (2)	154
C16—H16B···Cg2^i	0.98	2.96	3.704 (3)	133
C9—H9···N1^ii	1.00	2.56	3.380 (3)	139
C9—H9···N2^ii	1.00	2.48	3.457 (3)	166

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y−1/2, −z+3/2.

(II) 1-Acetyl-5-ferrocenyl-3-(2-pyridyl)-1H-pyrazole

Crystal data

[Fe(C5H5)(C15H12N3O)]	F(000) = 768
Mr = 371.22	Dx = 1.486 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.4790 (15) Å	Cell parameters from 25 reflections
b = 8.9290 (18) Å	θ = 9–15°
c = 24.942 (3) Å	µ = 0.92 mm^−1
β = 94.84 (3)°	T = 295 K
V = 1659.7 (5) Å^3	Plate, orange-red
Z = 4	0.21 × 0.13 × 0.11 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	2548 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 26.0°, θmin = 1.6°
ω/2θ scans	h = 0→9
Absorption correction: empirical ψ scan (North et al., 1968)	k = 0→10
Tmin = 0.830, Tmax = 0.901	l = −30→30
3503 measured reflections	3 standard reflections every 200 reflections
3247 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0431P)^2 + 1.3303P] where P = (Fo^2 + 2Fc^2)/3
3247 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.47 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe1	0.49868 (6)	0.68302 (5)	0.694494 (17)	0.03029 (15)
O1	0.6454 (4)	0.2218 (3)	0.62279 (10)	0.0596 (8)
N1	0.6860 (3)	0.4194 (3)	0.56772 (10)	0.0325 (6)
N2	0.7244 (4)	0.4587 (3)	0.51654 (10)	0.0365 (6)
N3	0.8451 (4)	0.8314 (3)	0.47962 (12)	0.0498 (8)
C1	0.2711 (5)	0.7693 (4)	0.72156 (16)	0.0502 (10)
H1	0.2179	0.7385	0.7521	0.060*
C2	0.2345 (5)	0.7113 (4)	0.66945 (16)	0.0524 (10)
H2	0.1526	0.6359	0.6595	0.063*
C3	0.3429 (5)	0.7869 (5)	0.63499 (16)	0.0569 (11)
H3	0.3463	0.7700	0.5983	0.068*
C4	0.4455 (6)	0.8928 (4)	0.66593 (18)	0.0592 (11)
H4	0.5280	0.9589	0.6531	0.071*
C5	0.4023 (5)	0.8820 (4)	0.71965 (17)	0.0538 (10)
H5	0.4513	0.9387	0.7485	0.065*
C6	0.5565 (4)	0.4605 (4)	0.69085 (13)	0.0358 (7)
H6	0.4778	0.3859	0.6777	0.043*
C7	0.5791 (5)	0.5114 (4)	0.74460 (13)	0.0423 (8)
H7	0.5187	0.4748	0.7730	0.051*
C8	0.7082 (5)	0.6271 (4)	0.74821 (14)	0.0431 (8)
H8	0.7475	0.6797	0.7792	0.052*
C9	0.7672 (4)	0.6486 (4)	0.69637 (13)	0.0361 (7)
H9	0.8510	0.7190	0.6872	0.043*
C10	0.6755 (4)	0.5432 (3)	0.66028 (12)	0.0311 (7)
C11	0.7038 (4)	0.5412 (3)	0.60287 (12)	0.0317 (7)
C12	0.7553 (4)	0.6570 (4)	0.57238 (13)	0.0385 (8)
H12	0.7787	0.7545	0.5840	0.046*
C13	0.7668 (4)	0.6020 (4)	0.51996 (13)	0.0344 (7)
C14	0.8167 (4)	0.6848 (4)	0.47246 (12)	0.0361 (7)
C15	0.8343 (5)	0.6147 (5)	0.42391 (14)	0.0521 (10)
H15	0.8156	0.5121	0.4203	0.063*
C16	0.8796 (6)	0.6983 (5)	0.38125 (15)	0.0618 (11)
H16	0.8921	0.6533	0.3482	0.074*
C17	0.9063 (5)	0.8491 (5)	0.38766 (16)	0.0568 (11)
H17	0.9357	0.9084	0.3590	0.068*
C18	0.8889 (6)	0.9099 (5)	0.43675 (16)	0.0584 (11)
H18	0.9085	1.0122	0.4410	0.070*
C19	0.6552 (4)	0.2652 (4)	0.57789 (14)	0.0382 (8)
C20	0.6403 (6)	0.1652 (4)	0.52993 (15)	0.0529 (10)
H20A	0.6519	0.2235	0.4981	0.079*	0.50
H20B	0.5257	0.1162	0.5273	0.079*	0.50
H20C	0.7339	0.0914	0.5335	0.079*	0.50
H20D	0.6224	0.0638	0.5412	0.079*	0.50
H20E	0.7486	0.1712	0.5119	0.079*	0.50
H20F	0.5404	0.1960	0.5058	0.079*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0272 (2)	0.0299 (2)	0.0347 (2)	0.0008 (2)	0.00769 (17)	−0.0019 (2)
O1	0.101 (2)	0.0343 (14)	0.0460 (15)	0.0008 (14)	0.0212 (15)	0.0024 (11)
N2	0.0365 (15)	0.0411 (16)	0.0330 (14)	0.0028 (13)	0.0090 (12)	0.0003 (12)
N1	0.0341 (14)	0.0306 (14)	0.0337 (14)	0.0000 (11)	0.0080 (11)	−0.0005 (11)
N3	0.063 (2)	0.0408 (17)	0.0485 (17)	−0.0008 (15)	0.0199 (15)	0.0026 (14)
C1	0.040 (2)	0.051 (2)	0.062 (2)	0.0088 (17)	0.0211 (18)	−0.0130 (19)
C2	0.0307 (18)	0.058 (2)	0.069 (3)	0.0082 (17)	0.0027 (17)	−0.015 (2)
C3	0.054 (2)	0.068 (3)	0.047 (2)	0.026 (2)	−0.0012 (18)	0.006 (2)
C4	0.053 (2)	0.038 (2)	0.087 (3)	0.0099 (19)	0.009 (2)	0.019 (2)
C5	0.052 (2)	0.038 (2)	0.072 (3)	0.0089 (18)	0.010 (2)	−0.0173 (19)
C6	0.0372 (17)	0.0286 (16)	0.0427 (19)	0.0020 (14)	0.0107 (15)	−0.0004 (14)
C10	0.0288 (15)	0.0301 (16)	0.0347 (16)	0.0056 (13)	0.0053 (13)	−0.0006 (13)
C9	0.0264 (15)	0.0408 (18)	0.0414 (18)	0.0024 (14)	0.0048 (13)	−0.0043 (15)
C8	0.041 (2)	0.051 (2)	0.0354 (17)	0.0055 (16)	−0.0036 (15)	−0.0079 (16)
C7	0.053 (2)	0.0412 (19)	0.0340 (18)	0.0085 (17)	0.0128 (15)	0.0062 (15)
C11	0.0279 (15)	0.0297 (16)	0.0385 (17)	0.0036 (13)	0.0081 (13)	−0.0031 (13)
C12	0.0426 (19)	0.0313 (17)	0.0432 (18)	0.0013 (14)	0.0121 (15)	−0.0018 (14)
C13	0.0314 (16)	0.0364 (18)	0.0362 (17)	0.0028 (14)	0.0071 (13)	−0.0003 (14)
C14	0.0313 (16)	0.0416 (18)	0.0361 (17)	0.0042 (15)	0.0074 (13)	0.0030 (15)
C15	0.069 (3)	0.050 (2)	0.0379 (19)	−0.004 (2)	0.0114 (18)	−0.0032 (17)
C16	0.075 (3)	0.075 (3)	0.038 (2)	−0.007 (2)	0.0143 (19)	−0.002 (2)
C17	0.055 (2)	0.068 (3)	0.049 (2)	0.000 (2)	0.0136 (19)	0.017 (2)
C18	0.065 (3)	0.048 (2)	0.064 (3)	−0.001 (2)	0.018 (2)	0.013 (2)
C19	0.0368 (18)	0.0340 (17)	0.044 (2)	0.0039 (14)	0.0053 (15)	−0.0026 (15)
C20	0.066 (2)	0.037 (2)	0.055 (2)	−0.0003 (18)	0.0032 (19)	−0.0118 (18)

Geometric parameters (Å, º)

Fe1—C1	2.035 (3)	C6—C10	1.426 (4)
Fe1—C2	2.037 (4)	C6—H6	0.9300
Fe1—C3	2.032 (4)	C7—H7	0.9300
Fe1—C4	2.032 (4)	C8—C7	1.412 (5)
Fe1—C5	2.036 (4)	C8—H8	0.9300
Fe1—C6	2.037 (3)	C9—C8	1.414 (5)
Fe1—C7	2.036 (3)	C9—H9	0.9300
Fe1—C8	2.036 (3)	C10—C9	1.436 (4)
Fe1—C9	2.028 (3)	C10—C11	1.465 (4)
Fe1—C10	2.056 (3)	C11—C12	1.358 (4)
O1—C19	1.193 (4)	C12—C13	1.406 (4)
N1—N2	1.378 (3)	C12—H12	0.9300
N1—C11	1.396 (4)	C13—C14	1.471 (4)
N1—C19	1.422 (4)	C14—C15	1.379 (5)
N2—C13	1.319 (4)	C15—C16	1.366 (5)
N3—C14	1.336 (4)	C15—H15	0.9300
N3—C18	1.342 (4)	C16—C17	1.368 (6)
C1—C2	1.404 (5)	C16—H16	0.9300
C1—H1	0.9300	C17—C18	1.356 (5)
C2—C3	1.403 (6)	C17—H17	0.9300
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.407 (6)	C19—C20	1.489 (5)
C3—H3	0.9300	C20—H20A	0.9600
C4—C5	1.408 (6)	C20—H20B	0.9600
C4—H4	0.9300	C20—H20C	0.9600
C1—C5	1.410 (5)	C20—H20D	0.9600
C5—H5	0.9300	C20—H20E	0.9600
C6—C7	1.412 (4)	C20—H20F	0.9600
C9—Fe1—C4	108.18 (16)	Fe1—C5—H5	126.0
C9—Fe1—C3	126.27 (15)	C7—C6—C10	108.1 (3)
C4—Fe1—C3	40.51 (16)	C7—C6—Fe1	69.65 (19)
C9—Fe1—C1	154.70 (14)	C10—C6—Fe1	70.29 (17)
C4—Fe1—C1	67.84 (17)	C7—C6—H6	126.0
C3—Fe1—C1	68.00 (16)	C10—C6—H6	126.0
C9—Fe1—C7	68.36 (14)	Fe1—C6—H6	125.7
C4—Fe1—C7	161.49 (17)	C6—C10—C9	106.9 (3)
C3—Fe1—C7	155.98 (17)	C6—C10—C11	131.6 (3)
C1—Fe1—C7	107.05 (15)	C9—C10—C11	121.3 (3)
C9—Fe1—C5	120.03 (15)	C6—C10—Fe1	68.93 (17)
C4—Fe1—C5	40.49 (16)	C9—C10—Fe1	68.38 (17)
C3—Fe1—C5	68.33 (17)	C11—C10—Fe1	124.3 (2)
C1—Fe1—C5	40.52 (15)	C8—C9—C10	108.4 (3)
C7—Fe1—C5	124.16 (15)	C8—C9—Fe1	69.96 (19)
C9—Fe1—C8	40.72 (13)	C10—C9—Fe1	70.45 (17)
C4—Fe1—C8	125.02 (17)	C8—C9—H9	125.8
C3—Fe1—C8	162.67 (17)	C10—C9—H9	125.8
C1—Fe1—C8	119.57 (15)	Fe1—C9—H9	125.4
C7—Fe1—C8	40.57 (14)	C7—C8—C9	107.8 (3)
C5—Fe1—C8	106.50 (16)	C7—C8—Fe1	69.70 (19)
C9—Fe1—C2	163.48 (14)	C9—C8—Fe1	69.32 (18)
C4—Fe1—C2	67.79 (17)	C7—C8—H8	126.1
C3—Fe1—C2	40.35 (16)	C9—C8—H8	126.1
C1—Fe1—C2	40.35 (15)	Fe1—C8—H8	126.4
C7—Fe1—C2	120.67 (16)	C8—C7—C6	108.8 (3)
C5—Fe1—C2	68.10 (16)	C8—C7—Fe1	69.7 (2)
C8—Fe1—C2	154.81 (16)	C6—C7—Fe1	69.78 (19)
C9—Fe1—C6	68.89 (13)	C8—C7—H7	125.6
C4—Fe1—C6	156.89 (16)	C6—C7—H7	125.6
C3—Fe1—C6	121.56 (16)	Fe1—C7—H7	126.5
C1—Fe1—C6	124.80 (15)	C12—C11—N1	104.9 (3)
C7—Fe1—C6	40.58 (13)	C12—C11—C10	127.5 (3)
C5—Fe1—C6	161.23 (15)	N1—C11—C10	127.5 (3)
C8—Fe1—C6	68.63 (14)	C11—C12—C13	107.3 (3)
C2—Fe1—C6	108.14 (15)	C11—C12—H12	126.4
C9—Fe1—C10	41.16 (12)	C13—C12—H12	126.4
C4—Fe1—C10	121.88 (15)	N2—C13—C12	111.5 (3)
C3—Fe1—C10	108.86 (14)	N2—C13—C14	120.7 (3)
C1—Fe1—C10	162.38 (14)	C12—C13—C14	127.8 (3)
C7—Fe1—C10	68.33 (13)	N3—C14—C15	122.4 (3)
C5—Fe1—C10	156.14 (15)	N3—C14—C13	115.7 (3)
C8—Fe1—C10	68.77 (13)	C15—C14—C13	121.9 (3)
C2—Fe1—C10	126.11 (14)	C16—C15—C14	119.0 (4)
C6—Fe1—C10	40.78 (12)	C16—C15—H15	120.5
C13—N2—N1	104.8 (3)	C14—C15—H15	120.5
N2—N1—C11	111.5 (3)	C15—C16—C17	119.4 (4)
N2—N1—C19	117.5 (3)	C15—C16—H16	120.3
C11—N1—C19	130.6 (3)	C17—C16—H16	120.3
C14—N3—C18	116.9 (3)	C18—C17—C16	118.4 (4)
C2—C1—C5	108.3 (4)	C18—C17—H17	120.8
C2—C1—Fe1	69.9 (2)	C16—C17—H17	120.8
C5—C1—Fe1	69.8 (2)	N3—C18—C17	124.0 (4)
C2—C1—H1	125.9	N3—C18—H18	118.0
C5—C1—H1	125.9	C17—C18—H18	118.0
Fe1—C1—H1	126.0	O1—C19—N1	120.4 (3)
C3—C2—C1	108.2 (4)	O1—C19—C20	123.6 (3)
C3—C2—Fe1	69.6 (2)	N1—C19—C20	116.1 (3)
C1—C2—Fe1	69.7 (2)	C19—C20—H20A	109.5
C3—C2—H2	125.9	C19—C20—H20B	109.5
C1—C2—H2	125.9	H20A—C20—H20B	109.5
Fe1—C2—H2	126.3	C19—C20—H20C	109.5
C2—C3—C4	107.7 (4)	H20A—C20—H20C	109.5
C2—C3—Fe1	70.0 (2)	H20B—C20—H20C	109.5
C4—C3—Fe1	69.7 (2)	C19—C20—H20D	109.5
C2—C3—H3	126.2	H20A—C20—H20D	141.1
C4—C3—H3	126.2	H20B—C20—H20D	56.3
Fe1—C3—H3	125.7	H20C—C20—H20D	56.3
C3—C4—C5	108.5 (4)	C19—C20—H20E	109.5
C3—C4—Fe1	69.8 (2)	H20A—C20—H20E	56.3
C5—C4—Fe1	69.9 (2)	H20B—C20—H20E	141.1
C3—C4—H4	125.7	H20C—C20—H20E	56.3
C5—C4—H4	125.7	H20D—C20—H20E	109.5
Fe1—C4—H4	126.2	C19—C20—H20F	109.5
C4—C5—C1	107.3 (4)	H20A—C20—H20F	56.3
C4—C5—Fe1	69.6 (2)	H20B—C20—H20F	56.3
C1—C5—Fe1	69.7 (2)	H20C—C20—H20F	141.1
C4—C5—H5	126.3	H20D—C20—H20F	109.5
C1—C5—H5	126.3	H20E—C20—H20F	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1^i	0.93	2.54	3.416 (4)	158

Symmetry code: (i) −x+3/2, y+1/2, −z+3/2.