1-(2,5-Dimethoxy­phen­yl)-3-ferrocenyl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one

Liu, J.-B.; Dai, H.; Li, L.-C.; Tao, W.-F.; Fang, J.-X.

doi:10.1107/S1600536805038699

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1-(2,5-Dimethoxyphenyl)-3-ferrocenyl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one

J.-B. Liu, H. Dai, L.-C. Li, W.-F. Tao and J.-X. Fang

In the title compound, [Fe(C₅H₅)(C₁₈H₁₆N₃O₃)], the propene plane is tilted from its parent cyclopentadienyl ring by a small dihedral angle [17.9 (5)°], whereas the triazole and dimethoxyphenyl groups are nearly perpendicular to the propene plane [dihedral angles 75.9 (2) and 67.9 (2)°, respectively]. The cyclopentadienyl rings exhibit an almost eclipsed geometry.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038699/xu6063sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038699/xu6063Isup2.hkl Contains datablock I

CCDC reference: 296708

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
R factor = 0.049
wR factor = 0.129
Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

We are interested in 1H-1,2,4-triazole derivatives because of their biological activities (Moreno-Manas et al., 1992; Chu et al., 1999; Liu et al., 1998). As part of an investigation on ferrocenyl-triazole derivatives (Fang et al., 2003; Jin et al., 2005), we report here the structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1. The Fe—C bond lengths range from 2.021 (3) to 2.042 (3) Å. The Fe1···Cg1 and Fe1···Cg2 distances are 1.634 (2) and 1.647 (2) Å, respectively (where Cg is the centroid of the five rings of the ferrocene). The cyclopentadienyl rings of the ferrocene are in an almost eclipsed geometry. While the propene plane tilts to the η(C₅H₄) ring of the ferrocene with a small dihedral angle of 17.9 (5)°, the dimethoxyphenyl and triazole rings are nearly perpendicular to the propene plane, the dihedral angles being 75.9 (2) and 67.9 (2)°, respectively.

Experimental top

1-(2,5-Dimethoxyphenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone (10 mmol) and ferrocenecarboxaldehyde (11 mmol) were dissolved in a dry toluene solution (50 ml). To the solution five drops of piperidine and five drops of glacial acetic acid were added at room temperature under a nitrogen atmosphere. The mixture was refluxed for 6 h, meanwhile the water generated in the reaction was evaporated. The toluene was evaporated under reduced pressure, and the residue was then purified by column chromatography on silica gel with petroleum ether/ethyl acetate (v/v = 4:1). Recrystallization from a petroleum ether/ethyl acetate solution (v/v = 3:1) gave single crystals of (I) (yield 70.0%).

Computing details top

Data collection: SMART (Bruker,1998); cell refinement: SAINT; data reduction: SAINT (Bruker,1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).

1-(2,5-Dimethoxyphenyl)-3-ferrocenyl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one top

Crystal data top

[Fe(C₅H₅)(C₁₈H₁₆N₃O₃)]	F(000) = 920
M_r = 443.28	D_x = 1.433 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2484 reflections
a = 7.292 (2) Å	θ = 2.5–24.3°
b = 20.226 (5) Å	µ = 0.76 mm⁻¹
c = 13.956 (4) Å	T = 294 K
β = 93.669 (5)°	Block, black
V = 2054.2 (10) Å³	0.24 × 0.22 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4181 independent reflections
Radiation source: fine-focus sealed tube	2551 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ϕ and ω scans	θ_max = 26.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
T_min = 0.826, T_max = 0.878	k = −22→25
11212 measured reflections	l = −11→17

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0659P)²] where P = (F_o² + 2F_c²)/3
4181 reflections	(Δ/σ)_max = 0.002
273 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₈H₁₆N₃O₃)]	V = 2054.2 (10) Å³
M_r = 443.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.292 (2) Å	µ = 0.76 mm⁻¹
b = 20.226 (5) Å	T = 294 K
c = 13.956 (4) Å	0.24 × 0.22 × 0.18 mm
β = 93.669 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4181 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2551 reflections with I > 2σ(I)
T_min = 0.826, T_max = 0.878	R_int = 0.054
11212 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 0.99	Δρ_max = 0.40 e Å⁻³
4181 reflections	Δρ_min = −0.53 e Å⁻³
273 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	0.22765 (6)	1.01115 (2)	0.29240 (4)	0.03427 (18)
O1	0.5728 (3)	0.83702 (11)	0.5326 (2)	0.0584 (8)
O2	0.1496 (3)	0.76394 (11)	0.61889 (17)	0.0489 (6)
O3	0.6221 (3)	0.57989 (11)	0.47810 (19)	0.0522 (7)
N1	0.1376 (3)	0.81187 (12)	0.40552 (19)	0.0315 (6)
N2	0.1749 (4)	0.77970 (14)	0.3239 (2)	0.0469 (8)
N3	−0.1227 (4)	0.76715 (16)	0.3551 (2)	0.0562 (9)
C1	0.4268 (4)	0.81071 (15)	0.5090 (2)	0.0346 (8)
C2	0.3994 (4)	0.73906 (15)	0.5280 (2)	0.0305 (7)
C3	0.5257 (4)	0.69431 (16)	0.4930 (2)	0.0324 (8)
H3	0.6198	0.7095	0.4568	0.039*
C4	0.5103 (4)	0.62812 (17)	0.5122 (2)	0.0378 (9)
C5	0.3701 (5)	0.60550 (17)	0.5664 (3)	0.0439 (9)
H5	0.3588	0.5605	0.5781	0.053*
C6	0.2472 (4)	0.64926 (17)	0.6030 (2)	0.0438 (9)
H6	0.1559	0.6338	0.6408	0.053*
C7	0.2600 (4)	0.71656 (16)	0.5834 (2)	0.0348 (8)
C8	0.0054 (5)	0.7428 (2)	0.6765 (3)	0.0601 (11)
H8A	−0.0777	0.7147	0.6392	0.090*
H8B	−0.0598	0.7807	0.6980	0.090*
H8C	0.0570	0.7188	0.7312	0.090*
C9	0.7755 (5)	0.60015 (18)	0.4297 (3)	0.0624 (12)
H9A	0.7352	0.6246	0.3733	0.094*
H9B	0.8435	0.5620	0.4116	0.094*
H9C	0.8527	0.6277	0.4712	0.094*
C10	0.2776 (4)	0.84912 (15)	0.4585 (2)	0.0299 (7)
C11	−0.0398 (4)	0.80330 (16)	0.4223 (3)	0.0445 (9)
H11	−0.0961	0.8207	0.4746	0.053*
C12	0.0140 (6)	0.75470 (19)	0.2965 (3)	0.0555 (11)
H12	−0.0048	0.7301	0.2405	0.067*
C13	0.2768 (4)	0.91498 (15)	0.4592 (2)	0.0328 (8)
H13	0.3703	0.9346	0.4978	0.039*
C14	0.1516 (4)	0.96037 (16)	0.4088 (2)	0.0334 (8)
C15	0.0244 (4)	0.94979 (17)	0.3284 (3)	0.0420 (9)
H15	−0.0041	0.9092	0.2998	0.050*
C16	−0.0507 (5)	1.01155 (19)	0.2996 (3)	0.0523 (10)
H16	−0.1380	1.0187	0.2491	0.063*
C17	0.0299 (5)	1.06069 (18)	0.3608 (3)	0.0525 (11)
H17	0.0042	1.1057	0.3573	0.063*
C18	0.1552 (5)	1.03047 (16)	0.4276 (3)	0.0434 (9)
H18	0.2275	1.0518	0.4754	0.052*
C19	0.3665 (6)	0.9642 (2)	0.1908 (3)	0.0606 (11)
H19	0.3482	0.9207	0.1709	0.073*
C20	0.2777 (5)	1.0194 (2)	0.1511 (3)	0.0542 (10)
H20	0.1898	1.0191	0.0998	0.065*
C21	0.3416 (5)	1.0753 (2)	0.2004 (3)	0.0545 (11)
H21	0.3045	1.1186	0.1879	0.065*
C22	0.4726 (5)	1.0548 (2)	0.2728 (3)	0.0609 (12)
H22	0.5366	1.0820	0.3170	0.073*
C23	0.4890 (5)	0.9857 (2)	0.2663 (3)	0.0636 (12)
H23	0.5668	0.9590	0.3049	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0211 (3)	0.0380 (3)	0.0451 (3)	−0.0006 (2)	0.0126 (2)	0.0024 (2)
O1	0.0296 (13)	0.0420 (15)	0.102 (2)	−0.0102 (12)	−0.0110 (14)	−0.0016 (14)
O2	0.0420 (15)	0.0492 (15)	0.0581 (16)	0.0013 (12)	0.0243 (13)	0.0026 (12)
O3	0.0454 (15)	0.0387 (14)	0.0743 (19)	0.0054 (11)	0.0180 (14)	0.0042 (13)
N1	0.0248 (14)	0.0321 (15)	0.0378 (16)	−0.0040 (11)	0.0035 (12)	−0.0004 (12)
N2	0.0438 (19)	0.0548 (19)	0.0415 (18)	0.0041 (15)	−0.0026 (15)	−0.0107 (15)
N3	0.045 (2)	0.055 (2)	0.067 (2)	−0.0186 (16)	−0.0106 (19)	0.0046 (18)
C1	0.0287 (17)	0.0350 (18)	0.041 (2)	−0.0030 (15)	0.0082 (15)	−0.0001 (15)
C2	0.0233 (16)	0.0344 (18)	0.0335 (18)	−0.0028 (13)	−0.0012 (14)	0.0013 (15)
C3	0.0203 (17)	0.039 (2)	0.038 (2)	−0.0042 (13)	0.0042 (15)	0.0042 (15)
C4	0.0335 (19)	0.037 (2)	0.043 (2)	0.0004 (15)	0.0010 (17)	0.0024 (16)
C5	0.045 (2)	0.038 (2)	0.049 (2)	−0.0015 (16)	0.0112 (18)	0.0117 (17)
C6	0.034 (2)	0.049 (2)	0.049 (2)	−0.0057 (16)	0.0097 (17)	0.0145 (18)
C7	0.0285 (18)	0.042 (2)	0.0337 (19)	−0.0016 (15)	0.0035 (15)	0.0039 (16)
C8	0.046 (2)	0.068 (3)	0.071 (3)	0.0032 (19)	0.034 (2)	0.008 (2)
C9	0.054 (3)	0.057 (3)	0.079 (3)	0.004 (2)	0.031 (2)	−0.004 (2)
C10	0.0239 (16)	0.0301 (18)	0.0366 (19)	−0.0069 (13)	0.0080 (14)	−0.0011 (15)
C11	0.0278 (18)	0.048 (2)	0.058 (3)	−0.0104 (16)	0.0080 (18)	0.0020 (19)
C12	0.060 (3)	0.052 (2)	0.052 (3)	0.001 (2)	−0.017 (2)	−0.012 (2)
C13	0.0261 (17)	0.037 (2)	0.0359 (19)	−0.0094 (14)	0.0069 (15)	−0.0007 (15)
C14	0.0268 (17)	0.0325 (18)	0.043 (2)	−0.0020 (14)	0.0151 (16)	0.0028 (16)
C15	0.0201 (17)	0.045 (2)	0.061 (2)	−0.0079 (15)	0.0049 (17)	0.0066 (18)
C16	0.0211 (17)	0.065 (3)	0.072 (3)	0.0053 (18)	0.0120 (18)	0.023 (2)
C17	0.046 (2)	0.043 (2)	0.073 (3)	0.0144 (19)	0.034 (2)	0.009 (2)
C18	0.043 (2)	0.039 (2)	0.051 (2)	−0.0009 (16)	0.0240 (18)	−0.0007 (17)
C19	0.045 (2)	0.067 (3)	0.073 (3)	0.004 (2)	0.027 (2)	−0.019 (2)
C20	0.040 (2)	0.083 (3)	0.041 (2)	−0.002 (2)	0.0126 (18)	0.002 (2)
C21	0.047 (2)	0.055 (3)	0.064 (3)	−0.0104 (19)	0.022 (2)	0.014 (2)
C22	0.038 (2)	0.091 (4)	0.055 (3)	−0.026 (2)	0.018 (2)	−0.009 (2)
C23	0.025 (2)	0.098 (4)	0.070 (3)	0.017 (2)	0.018 (2)	0.020 (3)

Geometric parameters (Å, º) top

Fe1—C15	2.021 (3)	C6—H6	0.9300
Fe1—C22	2.026 (4)	C8—H8A	0.9600
Fe1—C14	2.029 (3)	C8—H8B	0.9600
Fe1—C23	2.030 (4)	C8—H8C	0.9600
Fe1—C18	2.030 (4)	C9—H9A	0.9600
Fe1—C19	2.031 (4)	C9—H9B	0.9600
Fe1—C20	2.036 (4)	C9—H9C	0.9600
Fe1—C16	2.039 (3)	C10—C13	1.332 (4)
Fe1—C21	2.039 (4)	C11—H11	0.9300
Fe1—C17	2.042 (3)	C12—H12	0.9300
O1—C1	1.216 (4)	C13—C14	1.445 (4)
O2—C7	1.365 (4)	C13—H13	0.9300
O2—C8	1.430 (4)	C14—C15	1.426 (4)
O3—C4	1.376 (4)	C14—C18	1.442 (5)
O3—C9	1.405 (4)	C15—C16	1.412 (5)
N1—C11	1.340 (4)	C15—H15	0.9300
N1—N2	1.354 (4)	C16—C17	1.414 (5)
N1—C10	1.436 (4)	C16—H16	0.9300
N2—C12	1.312 (4)	C17—C18	1.403 (5)
N3—C11	1.307 (4)	C17—H17	0.9300
N3—C12	1.353 (5)	C18—H18	0.9300
C1—C2	1.489 (4)	C19—C20	1.389 (5)
C1—C10	1.478 (4)	C19—C23	1.406 (6)
C2—C7	1.393 (4)	C19—H19	0.9300
C2—C3	1.401 (4)	C20—C21	1.388 (5)
C3—C4	1.371 (4)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.407 (5)
C4—C5	1.387 (4)	C21—H21	0.9300
C5—C6	1.381 (5)	C22—C23	1.407 (6)
C5—H5	0.9300	C22—H22	0.9300
C6—C7	1.392 (4)	C23—H23	0.9300

C15—Fe1—C22	165.40 (17)	O3—C9—H9A	109.5
C15—Fe1—C14	41.22 (13)	O3—C9—H9B	109.5
C22—Fe1—C14	128.08 (16)	H9A—C9—H9B	109.5
C15—Fe1—C23	126.92 (17)	O3—C9—H9C	109.5
C22—Fe1—C23	40.59 (16)	H9A—C9—H9C	109.5
C14—Fe1—C23	108.86 (15)	H9B—C9—H9C	109.5
C15—Fe1—C18	69.44 (15)	C13—C10—N1	121.7 (3)
C22—Fe1—C18	108.98 (16)	C13—C10—C1	121.7 (3)
C14—Fe1—C18	41.62 (13)	N1—C10—C1	116.6 (3)
C23—Fe1—C18	121.27 (17)	N3—C11—N1	110.8 (3)
C15—Fe1—C19	107.02 (16)	N3—C11—H11	124.6
C22—Fe1—C19	68.07 (17)	N1—C11—H11	124.6
C14—Fe1—C19	119.76 (16)	N2—C12—N3	115.6 (3)
C23—Fe1—C19	40.51 (16)	N2—C12—H12	122.2
C18—Fe1—C19	155.57 (17)	N3—C12—H12	122.2
C15—Fe1—C20	118.10 (16)	C10—C13—C14	129.4 (3)
C22—Fe1—C20	67.63 (16)	C10—C13—H13	115.3
C14—Fe1—C20	153.19 (15)	C14—C13—H13	115.3
C23—Fe1—C20	67.54 (16)	C15—C14—C18	107.1 (3)
C18—Fe1—C20	163.42 (15)	C15—C14—C13	130.3 (3)
C19—Fe1—C20	39.95 (16)	C18—C14—C13	122.1 (3)
C15—Fe1—C16	40.71 (13)	C15—C14—Fe1	69.10 (18)
C22—Fe1—C16	153.36 (18)	C18—C14—Fe1	69.23 (18)
C14—Fe1—C16	68.82 (14)	C13—C14—Fe1	121.0 (2)
C23—Fe1—C16	163.55 (18)	C16—C15—C14	108.2 (3)
C18—Fe1—C16	68.56 (16)	C16—C15—Fe1	70.32 (19)
C19—Fe1—C16	125.36 (18)	C14—C15—Fe1	69.68 (18)
C20—Fe1—C16	106.74 (17)	C16—C15—H15	125.9
C15—Fe1—C21	151.89 (16)	C14—C15—H15	125.9
C22—Fe1—C21	40.51 (15)	Fe1—C15—H15	125.7
C14—Fe1—C21	165.79 (16)	C15—C16—C17	108.1 (3)
C23—Fe1—C21	67.84 (17)	C15—C16—Fe1	68.98 (18)
C18—Fe1—C21	127.13 (15)	C17—C16—Fe1	69.9 (2)
C19—Fe1—C21	67.43 (18)	C15—C16—H16	125.9
C20—Fe1—C21	39.83 (15)	C17—C16—H16	125.9
C16—Fe1—C21	118.41 (16)	Fe1—C16—H16	126.8
C15—Fe1—C17	68.55 (15)	C18—C17—C16	108.9 (3)
C22—Fe1—C17	120.26 (18)	C18—C17—Fe1	69.4 (2)
C14—Fe1—C17	68.72 (14)	C16—C17—Fe1	69.6 (2)
C23—Fe1—C17	155.20 (19)	C18—C17—H17	125.6
C18—Fe1—C17	40.32 (14)	C16—C17—H17	125.6
C19—Fe1—C17	162.67 (18)	Fe1—C17—H17	127.0
C20—Fe1—C17	126.03 (16)	C17—C18—C14	107.7 (3)
C16—Fe1—C17	40.54 (15)	C17—C18—Fe1	70.3 (2)
C21—Fe1—C17	108.10 (16)	C14—C18—Fe1	69.14 (18)
C7—O2—C8	117.8 (3)	C17—C18—H18	126.2
C4—O3—C9	117.9 (3)	C14—C18—H18	126.2
C11—N1—N2	109.5 (3)	Fe1—C18—H18	126.0
C11—N1—C10	129.8 (3)	C20—C19—C23	107.9 (4)
N2—N1—C10	120.7 (3)	C20—C19—Fe1	70.2 (2)
C12—N2—N1	101.9 (3)	C23—C19—Fe1	69.7 (2)
C11—N3—C12	102.3 (3)	C20—C19—H19	126.0
O1—C1—C10	120.2 (3)	C23—C19—H19	126.0
O1—C1—C2	120.2 (3)	Fe1—C19—H19	125.6
C10—C1—C2	119.5 (3)	C21—C20—C19	108.9 (4)
C7—C2—C3	120.1 (3)	C21—C20—Fe1	70.2 (2)
C7—C2—C1	121.9 (3)	C19—C20—Fe1	69.8 (2)
C3—C2—C1	117.9 (3)	C21—C20—H20	125.6
C4—C3—C2	119.9 (3)	C19—C20—H20	125.6
C4—C3—H3	120.1	Fe1—C20—H20	126.0
C2—C3—H3	120.1	C20—C21—C22	108.0 (4)
C3—C4—O3	124.5 (3)	C20—C21—Fe1	70.0 (2)
C3—C4—C5	120.1 (3)	C22—C21—Fe1	69.3 (2)
O3—C4—C5	115.4 (3)	C20—C21—H21	126.0
C6—C5—C4	120.6 (3)	C22—C21—H21	126.0
C6—C5—H5	119.7	Fe1—C21—H21	126.3
C4—C5—H5	119.7	C23—C22—C21	107.6 (4)
C5—C6—C7	120.0 (3)	C23—C22—Fe1	69.8 (2)
C5—C6—H6	120.0	C21—C22—Fe1	70.2 (2)
C7—C6—H6	120.0	C23—C22—H22	126.2
O2—C7—C2	116.1 (3)	C21—C22—H22	126.2
O2—C7—C6	124.5 (3)	Fe1—C22—H22	125.3
C2—C7—C6	119.3 (3)	C19—C23—C22	107.7 (4)
O2—C8—H8A	109.5	C19—C23—Fe1	69.8 (2)
O2—C8—H8B	109.5	C22—C23—Fe1	69.6 (2)
H8A—C8—H8B	109.5	C19—C23—H23	126.2
O2—C8—H8C	109.5	C22—C23—H23	126.2
H8A—C8—H8C	109.5	Fe1—C23—H23	126.0
H8B—C8—H8C	109.5

C11—N1—N2—C12	1.0 (4)	C19—Fe1—C17—C16	40.8 (6)
C10—N1—N2—C12	−177.7 (3)	C20—Fe1—C17—C16	72.4 (3)
O1—C1—C2—C7	121.6 (4)	C21—Fe1—C17—C16	112.8 (2)
C10—C1—C2—C7	−60.4 (4)	C16—C17—C18—C14	−0.7 (4)
O1—C1—C2—C3	−54.7 (5)	Fe1—C17—C18—C14	−59.3 (2)
C10—C1—C2—C3	123.3 (3)	C16—C17—C18—Fe1	58.5 (2)
C7—C2—C3—C4	0.9 (5)	C15—C14—C18—C17	1.1 (3)
C1—C2—C3—C4	177.3 (3)	C13—C14—C18—C17	174.3 (3)
C2—C3—C4—O3	177.2 (3)	Fe1—C14—C18—C17	60.0 (2)
C2—C3—C4—C5	−0.1 (5)	C15—C14—C18—Fe1	−58.9 (2)
C9—O3—C4—C3	7.8 (5)	C13—C14—C18—Fe1	114.3 (3)
C9—O3—C4—C5	−174.8 (3)	C15—Fe1—C18—C17	−80.7 (2)
C3—C4—C5—C6	−1.3 (5)	C22—Fe1—C18—C17	114.7 (3)
O3—C4—C5—C6	−178.8 (3)	C14—Fe1—C18—C17	−118.8 (3)
C4—C5—C6—C7	1.9 (5)	C23—Fe1—C18—C17	157.8 (2)
C8—O2—C7—C2	−179.7 (3)	C19—Fe1—C18—C17	−166.7 (4)
C8—O2—C7—C6	−3.0 (5)	C20—Fe1—C18—C17	39.5 (6)
C3—C2—C7—O2	176.5 (3)	C16—Fe1—C18—C17	−37.0 (2)
C1—C2—C7—O2	0.3 (5)	C21—Fe1—C18—C17	73.1 (3)
C3—C2—C7—C6	−0.4 (5)	C15—Fe1—C18—C14	38.07 (18)
C1—C2—C7—C6	−176.6 (3)	C22—Fe1—C18—C14	−126.5 (2)
C5—C6—C7—O2	−177.6 (3)	C23—Fe1—C18—C14	−83.4 (2)
C5—C6—C7—C2	−1.0 (5)	C19—Fe1—C18—C14	−47.9 (4)
C11—N1—C10—C13	−70.9 (4)	C20—Fe1—C18—C14	158.3 (5)
N2—N1—C10—C13	107.5 (3)	C16—Fe1—C18—C14	81.8 (2)
C11—N1—C10—C1	111.5 (4)	C21—Fe1—C18—C14	−168.1 (2)
N2—N1—C10—C1	−70.1 (4)	C17—Fe1—C18—C14	118.8 (3)
O1—C1—C10—C13	−17.8 (5)	C15—Fe1—C19—C20	113.7 (3)
C2—C1—C10—C13	164.1 (3)	C22—Fe1—C19—C20	−80.9 (3)
O1—C1—C10—N1	159.8 (3)	C14—Fe1—C19—C20	156.7 (2)
C2—C1—C10—N1	−18.3 (4)	C23—Fe1—C19—C20	−118.8 (4)
C12—N3—C11—N1	−0.4 (4)	C18—Fe1—C19—C20	−168.7 (3)
N2—N1—C11—N3	−0.4 (4)	C16—Fe1—C19—C20	72.7 (3)
C10—N1—C11—N3	178.2 (3)	C21—Fe1—C19—C20	−37.0 (2)
N1—N2—C12—N3	−1.3 (4)	C17—Fe1—C19—C20	41.3 (6)
C11—N3—C12—N2	1.1 (5)	C15—Fe1—C19—C23	−127.5 (3)
N1—C10—C13—C14	−2.6 (5)	C22—Fe1—C19—C23	37.9 (2)
C1—C10—C13—C14	174.9 (3)	C14—Fe1—C19—C23	−84.5 (3)
C10—C13—C14—C15	−17.1 (5)	C18—Fe1—C19—C23	−49.9 (5)
C10—C13—C14—C18	171.3 (3)	C20—Fe1—C19—C23	118.8 (4)
C10—C13—C14—Fe1	−105.0 (3)	C16—Fe1—C19—C23	−168.5 (2)
C22—Fe1—C14—C15	−166.2 (2)	C21—Fe1—C19—C23	81.8 (3)
C23—Fe1—C14—C15	−125.0 (2)	C17—Fe1—C19—C23	160.1 (5)
C18—Fe1—C14—C15	118.8 (3)	C23—C19—C20—C21	−0.2 (4)
C19—Fe1—C14—C15	−81.9 (2)	Fe1—C19—C20—C21	59.5 (3)
C20—Fe1—C14—C15	−47.6 (4)	C23—C19—C20—Fe1	−59.7 (3)
C16—Fe1—C14—C15	37.7 (2)	C15—Fe1—C20—C21	157.1 (2)
C21—Fe1—C14—C15	160.9 (6)	C22—Fe1—C20—C21	−37.8 (2)
C17—Fe1—C14—C15	81.3 (2)	C14—Fe1—C20—C21	−169.4 (3)
C15—Fe1—C14—C18	−118.8 (3)	C23—Fe1—C20—C21	−81.9 (3)
C22—Fe1—C14—C18	74.9 (3)	C18—Fe1—C20—C21	43.6 (6)
C23—Fe1—C14—C18	116.2 (2)	C19—Fe1—C20—C21	−119.9 (4)
C19—Fe1—C14—C18	159.3 (2)	C16—Fe1—C20—C21	114.5 (3)
C20—Fe1—C14—C18	−166.5 (3)	C17—Fe1—C20—C21	74.2 (3)
C16—Fe1—C14—C18	−81.1 (2)	C15—Fe1—C20—C19	−83.1 (3)
C21—Fe1—C14—C18	42.1 (6)	C22—Fe1—C20—C19	82.1 (3)
C17—Fe1—C14—C18	−37.5 (2)	C14—Fe1—C20—C19	−49.6 (4)
C15—Fe1—C14—C13	125.3 (4)	C23—Fe1—C20—C19	38.0 (2)
C22—Fe1—C14—C13	−40.9 (4)	C18—Fe1—C20—C19	163.5 (5)
C23—Fe1—C14—C13	0.3 (3)	C16—Fe1—C20—C19	−125.6 (3)
C18—Fe1—C14—C13	−115.9 (3)	C21—Fe1—C20—C19	119.9 (4)
C19—Fe1—C14—C13	43.4 (3)	C17—Fe1—C20—C19	−165.9 (2)
C20—Fe1—C14—C13	77.7 (4)	C19—C20—C21—C22	−0.3 (4)
C16—Fe1—C14—C13	163.0 (3)	Fe1—C20—C21—C22	59.1 (2)
C21—Fe1—C14—C13	−73.7 (7)	C19—C20—C21—Fe1	−59.3 (3)
C17—Fe1—C14—C13	−153.3 (3)	C15—Fe1—C21—C20	−46.9 (4)
C18—C14—C15—C16	−1.0 (3)	C22—Fe1—C21—C20	119.3 (4)
C13—C14—C15—C16	−173.5 (3)	C14—Fe1—C21—C20	160.3 (5)
Fe1—C14—C15—C16	−60.0 (2)	C23—Fe1—C21—C20	81.0 (3)
C18—C14—C15—Fe1	59.0 (2)	C18—Fe1—C21—C20	−165.7 (2)
C13—C14—C15—Fe1	−113.5 (3)	C19—Fe1—C21—C20	37.1 (2)
C22—Fe1—C15—C16	167.1 (6)	C16—Fe1—C21—C20	−82.1 (3)
C14—Fe1—C15—C16	119.1 (3)	C17—Fe1—C21—C20	−125.0 (3)
C23—Fe1—C15—C16	−165.0 (3)	C15—Fe1—C21—C22	−166.1 (3)
C18—Fe1—C15—C16	80.7 (2)	C14—Fe1—C21—C22	41.1 (7)
C19—Fe1—C15—C16	−124.9 (3)	C23—Fe1—C21—C22	−38.2 (3)
C20—Fe1—C15—C16	−83.1 (3)	C18—Fe1—C21—C22	75.0 (3)
C21—Fe1—C15—C16	−51.1 (4)	C19—Fe1—C21—C22	−82.2 (3)
C17—Fe1—C15—C16	37.3 (2)	C20—Fe1—C21—C22	−119.3 (4)
C22—Fe1—C15—C14	48.0 (7)	C16—Fe1—C21—C22	158.6 (3)
C23—Fe1—C15—C14	75.9 (3)	C17—Fe1—C21—C22	115.7 (3)
C18—Fe1—C15—C14	−38.4 (2)	C20—C21—C22—C23	0.6 (4)
C19—Fe1—C15—C14	116.0 (2)	Fe1—C21—C22—C23	60.1 (3)
C20—Fe1—C15—C14	157.8 (2)	C20—C21—C22—Fe1	−59.5 (3)
C16—Fe1—C15—C14	−119.1 (3)	C15—Fe1—C22—C23	35.1 (7)
C21—Fe1—C15—C14	−170.2 (3)	C14—Fe1—C22—C23	73.5 (3)
C17—Fe1—C15—C14	−81.8 (2)	C18—Fe1—C22—C23	116.3 (3)
C14—C15—C16—C17	0.6 (4)	C19—Fe1—C22—C23	−37.8 (2)
Fe1—C15—C16—C17	−59.1 (2)	C20—Fe1—C22—C23	−81.1 (3)
C14—C15—C16—Fe1	59.6 (2)	C16—Fe1—C22—C23	−163.9 (4)
C22—Fe1—C16—C15	−172.8 (3)	C21—Fe1—C22—C23	−118.3 (4)
C14—Fe1—C16—C15	−38.1 (2)	C17—Fe1—C22—C23	159.1 (3)
C23—Fe1—C16—C15	46.8 (7)	C15—Fe1—C22—C21	153.3 (6)
C18—Fe1—C16—C15	−83.0 (2)	C14—Fe1—C22—C21	−168.2 (2)
C19—Fe1—C16—C15	74.1 (3)	C23—Fe1—C22—C21	118.3 (4)
C20—Fe1—C16—C15	113.9 (2)	C18—Fe1—C22—C21	−125.5 (2)
C21—Fe1—C16—C15	155.4 (2)	C19—Fe1—C22—C21	80.5 (3)
C17—Fe1—C16—C15	−119.8 (3)	C20—Fe1—C22—C21	37.2 (2)
C15—Fe1—C16—C17	119.8 (3)	C16—Fe1—C22—C21	−45.6 (5)
C22—Fe1—C16—C17	−53.0 (5)	C17—Fe1—C22—C21	−82.6 (3)
C14—Fe1—C16—C17	81.6 (2)	C20—C19—C23—C22	0.6 (4)
C23—Fe1—C16—C17	166.6 (5)	Fe1—C19—C23—C22	−59.5 (3)
C18—Fe1—C16—C17	36.8 (2)	C20—C19—C23—Fe1	60.1 (3)
C19—Fe1—C16—C17	−166.2 (2)	C21—C22—C23—C19	−0.7 (4)
C20—Fe1—C16—C17	−126.4 (2)	Fe1—C22—C23—C19	59.6 (3)
C21—Fe1—C16—C17	−84.9 (3)	C21—C22—C23—Fe1	−60.4 (2)
C15—C16—C17—C18	0.1 (4)	C15—Fe1—C23—C19	71.6 (3)
Fe1—C16—C17—C18	−58.4 (2)	C22—Fe1—C23—C19	−118.8 (4)
C15—C16—C17—Fe1	58.5 (2)	C14—Fe1—C23—C19	114.1 (3)
C15—Fe1—C17—C18	83.1 (2)	C18—Fe1—C23—C19	158.3 (2)
C22—Fe1—C17—C18	−84.0 (3)	C20—Fe1—C23—C19	−37.5 (2)
C14—Fe1—C17—C18	38.7 (2)	C16—Fe1—C23—C19	35.1 (7)
C23—Fe1—C17—C18	−50.4 (5)	C21—Fe1—C23—C19	−80.7 (3)
C19—Fe1—C17—C18	161.4 (5)	C17—Fe1—C23—C19	−166.0 (3)
C20—Fe1—C17—C18	−167.0 (2)	C15—Fe1—C23—C22	−169.6 (2)
C16—Fe1—C17—C18	120.6 (3)	C14—Fe1—C23—C22	−127.1 (2)
C21—Fe1—C17—C18	−126.6 (2)	C18—Fe1—C23—C22	−82.9 (3)
C15—Fe1—C17—C16	−37.5 (2)	C19—Fe1—C23—C22	118.8 (4)
C22—Fe1—C17—C16	155.5 (2)	C20—Fe1—C23—C22	81.3 (3)
C14—Fe1—C17—C16	−81.9 (2)	C16—Fe1—C23—C22	153.9 (5)
C23—Fe1—C17—C16	−171.0 (3)	C21—Fe1—C23—C22	38.1 (2)
C18—Fe1—C17—C16	−120.6 (3)	C17—Fe1—C23—C22	−47.2 (5)

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₈H₁₆N₃O₃)]
M_r	443.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	7.292 (2), 20.226 (5), 13.956 (4)
β (°)	93.669 (5)
V (Å³)	2054.2 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.24 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.826, 0.878
No. of measured, independent and observed [I > 2σ(I)] reflections	11212, 4181, 2551
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.129, 0.99
No. of reflections	4181
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.53

Computer programs: SMART (Bruker,1998), SAINT (Bruker,1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.

Selected geometric parameters (Å, º) top

O1—C1	1.216 (4)	C1—C10	1.478 (4)
C1—C2	1.489 (4)	C10—C13	1.332 (4)

O1—C1—C10	120.2 (3)	C13—C10—N1	121.7 (3)
O1—C1—C2	120.2 (3)	C13—C10—C1	121.7 (3)
C10—C1—C2	119.5 (3)	N1—C10—C1	116.6 (3)

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