N-Ferrocenylmethyl-2-nitro­aniline

Rahim, O.; Khelef, A.; Terki, B.; Mahboub, M.S.; Lanez, T.

doi:10.1107/S1600536812039177

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page m1318

https://doi.org/10.1107/S1600536812039177

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N-Ferrocenylmethyl-2-nitroaniline

Oumelkheir Rahim,^a Abdelhamid Khelef,^b Belgacem Terki,^a Mohammed Sadok Mahboub ^c and Touhami Lanez ^c ^*

^aDepartment of Chemistry, University of Ouargla, PO Box 511, Ouargla 30000, Algeria, ^bDepartment of Sciences and Technology, University Mohamed Khider of Biskra, PO Box 145, Biskra 07000, Algeria, and ^cVTRS Laboratory, Institute of Sciences and Technology, University of El-Oued, PO Box 789, El-Oued 39000, Algeria
^*Correspondence e-mail: lanezt@gmail.com

(Received 26 August 2012; accepted 13 September 2012; online 29 September 2012)

In the title compound, [Fe(C₅H₅)(C₁₂H₁₁N₂O₂)], the two cyclopentadienyl (Cp) rings are nearly eclipsed and parallel to each other, the dihedral angle between their mean planes being 2.54 (1)°. One of the Cp rings is substituted by a nitrobenzenamine group, which is essentially perpendicular to the substituted cyclopentadienyl ring, with an N—C(H₂)—C—C torsion angle of 89.8 (2)°. Intramolecular N—H⋯O and N—H⋯N hydrogen bonds occur. In the crystal, weak C—H⋯O hydrogen bonds link adjacent molecules.

Related literature

For background to the design and properties of ferrocene derivatives, see: Argyropoulos & Coutouli-Argyropoulou (2002 ); Cano et al. (1995 ); Shaabani & Shaghaghi (2010 ). For the synthesis of (ferrocenylmethyl)trimethylammonium iodide, see: Osgerby & Pauson (1961 ). For a related structure, see: Khelef et al. (2012 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₂H₁₁N₂O₂)]
M_r = 336.17
Monoclinic, P 2₁ /a
a = 10.3609 (3) Å
b = 7.8700 (2) Å
c = 17.7948 (7) Å
β = 93.043 (2)°
V = 1448.95 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.05 mm⁻¹
T = 293 K
0.3 × 0.1 × 0.1 mm

Data collection

Nonius KappaCCD diffractometer
14651 measured reflections
3204 independent reflections
2881 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.069
S = 1.05
3204 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H10⋯O2	0.827 (16)	2.01 (2)	2.6511 (19)	133.3 (18)
N1—H10⋯N2	0.827 (16)	2.624 (19)	2.961 (2)	106.0 (16)
C4—H4⋯O2ⁱ	0.93	2.57	3.283 (2)	134
Symmetry code: (i) x, y+1, z.

Data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812039177/zq2180sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039177/zq2180Isup2.hkl

checkCIF report

Comment top

Ferrocene derivatives have attracted the attention of many groups of researchers because of their utility in organic synthesis (Cano et al., 1995), medicinal chemistry (Argyropoulos & Coutouli-Argyropoulou, 2002) and in electrochemical studies (Shaabani & Shaghaghi, 2010). Herein, as a continuation of our research related to ferrocene derivatives (Khelef et al., 2012), we report the synthesis and X-ray diffraction characterization of the title compound.

In the title compound, [Fe(C₅H₅)(C₁₂H₁₁N₂O₂)], the two cyclopentadienyl (Cp) rings are nearly eclipsed and parallel to each other, the dihedral angle between the mean planes is 2.54 (1)°. One of the Cp ring is substituted by a nitrobenzenamine group which is essentially perpendicular to the substituted cyclopentadienyl ring, with a N—C(H₂)—C—C torsion angle of -79.83 (2)°. Weak C—H···O hydrogen bonds link adjacent molecules (Table 1).

Related literature top

For background to the design and properties of ferrocene derivatives, see: Argyropoulos & Coutouli-Argyropoulou (2002); Cano et al. (1995); Shaabani & Shaghaghi (2010). For the synthesis of (ferrocenylmethyl)trimethylammonium iodide, see: Osgerby & Pauson (1961). For a related structure, see: Khelef et al. (2012).

Experimental top

(Ferrocenylmethyl)trimethylammonium iodide was synthesized according to the reported methods of Osgerby & Pauson (Osgerby & Pauson, 1961). N-(Ferrocenylmethyl)-2-nitrobenzenamine was synthesized as follows: 2-nitroaniline (2.14 g, 15.48 mmol) was added in small portions to a well stirred solution of (ferrocenylmethyl)trimethylammonium iodide (6 g, 15.48 mmol) in water (120 cm³). The resulting mixture was then heated at 110–115°C for 6 h. It was then allowed to cool to room temperature. The obtained precipitate was separated by filtration, washed with water to remove any trace of unchanged (ferrocenylmethy)trimethylammonium iodide and finally recrystallized from ethanol 95% to produce the title compound as cinnabar-red needles (4.85 g, 92%; m.p. 110–112°C).

¹H NMR (CDCl₃): 4.14 (d, 2H, J = 4.73 Hz, CH₂Fc); 4.21 (t, 2H, J = 1.88 Hz, η⁵-C₅H₄ ortho); 4.27 (s, 5H, η⁵-C₅H₅); 4.28 (d, 2H, η⁵-C₅H₄ meta); 6.68 (t, 1H, J = 7.18 Hz, ArH); 6.90 (d, 1H, J = 8.49 Hz, ArH); 7.47 (t, 1H, J = 8.12 Hz, ArH); 8.23 (dd, 1H, J = 8.12 Hz, ArH); 8.37 (s, 1H, NH).

¹³C NMR (CDCl₃): 42.3 (-ve DEPT) (1 C, CH2Fc); 67.3 (2 C, η⁵-C₅H₄ meta); 68.1 (2 C, η⁵-C₅H₄); 68.8 (5 C, η⁵-C₅H₅); 84.5 (1 C, η⁵-C₅H₄); 113.8 (1 C, C₆H₄); 115.3 (1 C, C₆H₄);126.9 (1 C, C₆H₄); 131.8 (1 C, C₆H₄); 136.3 (1 C, C₆H₄); 144.9 (1 C, C₆H₄).

Structure description top

For background to the design and properties of ferrocene derivatives, see: Argyropoulos & Coutouli-Argyropoulou (2002); Cano et al. (1995); Shaabani & Shaghaghi (2010). For the synthesis of (ferrocenylmethyl)trimethylammonium iodide, see: Osgerby & Pauson (1961). For a related structure, see: Khelef et al. (2012).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme and 50% probability displacement ellipsoids.

N-Ferrocenylmethyl-2-nitroaniline top

Crystal data top

[Fe(C₅H₅)(C₁₂H₁₁N₂O₂)]	Z = 4
M_r = 336.17	F(000) = 696
Monoclinic, P2₁/a	D_x = 1.541 Mg m⁻³
Hall symbol: -P 2yab	Mo Kα radiation, λ = 0.71073 Å
a = 10.3609 (3) Å	θ = 1.2–27.4°
b = 7.8700 (2) Å	µ = 1.05 mm⁻¹
c = 17.7948 (7) Å	T = 293 K
β = 93.043 (2)°	Needle, red
V = 1448.95 (8) Å³	0.3 × 0.1 × 0.1 mm

Data collection top

Nonius KappaCCD diffractometer	2881 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 27.4°, θ_min = 1.2°
Detector resolution: 9 pixels mm^-1	h = −13→13
CCD scans	k = −10→10
14651 measured reflections	l = −22→22
3204 independent reflections

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0381P)² + 0.5817P] where P = (F_o² + 2F_c²)/3
3204 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₂H₁₁N₂O₂)]	V = 1448.95 (8) Å³
M_r = 336.17	Z = 4
Monoclinic, P2₁/a	Mo Kα radiation
a = 10.3609 (3) Å	µ = 1.05 mm⁻¹
b = 7.8700 (2) Å	T = 293 K
c = 17.7948 (7) Å	0.3 × 0.1 × 0.1 mm
β = 93.043 (2)°

Data collection top

Nonius KappaCCD diffractometer	2881 reflections with I > 2σ(I)
14651 measured reflections	R_int = 0.028
3204 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.40 e Å⁻³
3204 reflections	Δρ_min = −0.25 e Å⁻³
203 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
Fe	0.175327 (16)	0.49618 (2)	0.136596 (10)	0.01155 (8)
O1	−0.08310 (11)	−0.31659 (13)	0.38282 (7)	0.0288 (3)
O2	0.09259 (10)	−0.23198 (13)	0.33170 (7)	0.0277 (3)
N1	0.13730 (11)	0.09690 (15)	0.31440 (7)	0.0173 (2)
N2	−0.00760 (11)	−0.20171 (15)	0.36602 (7)	0.0190 (2)
C1	0.34295 (12)	0.55527 (19)	0.08304 (8)	0.0196 (3)
H1	0.3849	0.4876	0.0491	0.024*
C2	0.24330 (13)	0.67691 (19)	0.06407 (9)	0.0219 (3)
H2	0.2089	0.7022	0.0160	0.026*
C3	0.20652 (13)	0.75263 (18)	0.13377 (10)	0.0244 (3)
H3	0.1437	0.8360	0.1382	0.029*
C4	0.28328 (13)	0.67775 (19)	0.19565 (9)	0.0224 (3)
H4	0.2788	0.7042	0.2464	0.027*
C5	0.36735 (12)	0.55548 (19)	0.16420 (9)	0.0195 (3)
H5	0.4272	0.4879	0.1911	0.023*
C6	0.13517 (12)	0.24086 (17)	0.12877 (8)	0.0155 (3)
H6	0.1914	0.1558	0.1147	0.019*
C7	0.04727 (12)	0.33367 (17)	0.07798 (8)	0.0163 (3)
H7	0.0373	0.3199	0.0261	0.020*
C8	−0.02175 (12)	0.45125 (18)	0.12293 (8)	0.0162 (3)
H8	−0.0848	0.5271	0.1049	0.019*
C9	0.02341 (11)	0.43195 (17)	0.20148 (8)	0.0153 (3)
H9	−0.0059	0.4929	0.2420	0.018*
C10	0.12191 (11)	0.30137 (16)	0.20541 (8)	0.0144 (3)
C11	0.19956 (12)	0.23941 (18)	0.27600 (8)	0.0173 (3)
H11A	0.2846	0.2037	0.2619	0.021*
H11B	0.2111	0.3334	0.3110	0.021*
C12	0.03771 (12)	0.11221 (16)	0.36170 (7)	0.0141 (3)
C13	−0.00039 (12)	0.27404 (17)	0.38947 (8)	0.0161 (3)
H13	0.0417	0.3709	0.3735	0.019*
C14	−0.09834 (13)	0.29185 (17)	0.43954 (8)	0.0181 (3)
H14	−0.1180	0.3994	0.4573	0.022*
C15	−0.16826 (13)	0.15031 (18)	0.46392 (8)	0.0201 (3)
H15	−0.2335	0.1634	0.4974	0.024*
C16	−0.13745 (14)	−0.00804 (16)	0.43693 (9)	0.0191 (3)
H16	−0.1841	−0.1025	0.4514	0.023*
C17	−0.03569 (13)	−0.02881 (17)	0.38750 (8)	0.0157 (3)
H10	0.1571 (19)	−0.001 (2)	0.3026 (12)	0.028 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe	0.01011 (11)	0.00982 (11)	0.01488 (12)	−0.00088 (6)	0.00230 (8)	0.00070 (6)
O1	0.0366 (6)	0.0115 (5)	0.0392 (7)	−0.0041 (4)	0.0109 (5)	0.0019 (4)
O2	0.0323 (5)	0.0169 (5)	0.0353 (6)	0.0029 (4)	0.0149 (5)	−0.0029 (4)
N1	0.0198 (5)	0.0129 (6)	0.0197 (6)	0.0014 (4)	0.0052 (4)	0.0026 (5)
N2	0.0242 (6)	0.0137 (6)	0.0192 (6)	0.0005 (5)	0.0029 (5)	0.0014 (4)
C1	0.0156 (6)	0.0184 (7)	0.0256 (8)	−0.0041 (5)	0.0079 (5)	−0.0016 (6)
C2	0.0188 (6)	0.0216 (7)	0.0249 (8)	−0.0077 (5)	−0.0011 (5)	0.0106 (6)
C3	0.0159 (6)	0.0108 (6)	0.0470 (10)	−0.0022 (5)	0.0079 (6)	0.0012 (6)
C4	0.0212 (6)	0.0227 (7)	0.0238 (8)	−0.0102 (6)	0.0058 (5)	−0.0074 (6)
C5	0.0113 (5)	0.0196 (7)	0.0274 (8)	−0.0040 (5)	−0.0004 (5)	0.0041 (6)
C6	0.0153 (6)	0.0106 (6)	0.0211 (7)	−0.0020 (5)	0.0037 (5)	0.0001 (5)
C7	0.0154 (6)	0.0164 (6)	0.0172 (7)	−0.0047 (5)	0.0007 (5)	−0.0006 (5)
C8	0.0103 (5)	0.0154 (6)	0.0230 (7)	−0.0019 (5)	0.0012 (5)	0.0034 (5)
C9	0.0125 (5)	0.0144 (6)	0.0196 (7)	−0.0024 (5)	0.0052 (5)	0.0008 (5)
C10	0.0129 (5)	0.0128 (6)	0.0178 (7)	−0.0030 (5)	0.0024 (5)	0.0026 (5)
C11	0.0153 (6)	0.0185 (7)	0.0184 (7)	−0.0019 (5)	0.0027 (5)	0.0039 (5)
C12	0.0159 (6)	0.0129 (6)	0.0132 (6)	0.0004 (5)	−0.0017 (5)	0.0021 (5)
C13	0.0196 (6)	0.0109 (6)	0.0179 (7)	−0.0018 (5)	−0.0004 (5)	0.0017 (5)
C14	0.0227 (6)	0.0124 (6)	0.0189 (7)	0.0032 (5)	−0.0004 (5)	−0.0006 (5)
C15	0.0218 (6)	0.0182 (7)	0.0208 (7)	0.0036 (5)	0.0066 (5)	0.0019 (5)
C16	0.0208 (7)	0.0140 (7)	0.0229 (8)	−0.0007 (5)	0.0052 (6)	0.0039 (5)
C17	0.0197 (6)	0.0104 (6)	0.0169 (7)	0.0015 (5)	0.0014 (5)	0.0016 (5)

Geometric parameters (Å, º) top

Fe—C3	2.0450 (14)	C4—H4	0.9300
Fe—C6	2.0552 (13)	C5—H5	0.9300
Fe—C10	2.0562 (13)	C6—C7	1.4466 (19)
Fe—C9	2.0638 (12)	C6—C10	1.4579 (19)
Fe—C4	2.0669 (14)	C6—H6	0.9300
Fe—C2	2.0691 (14)	C7—C8	1.4382 (19)
Fe—C8	2.0738 (12)	C7—H7	0.9300
Fe—C5	2.0769 (13)	C8—C9	1.458 (2)
Fe—C1	2.0776 (13)	C8—H8	0.9300
Fe—C7	2.0826 (13)	C9—C10	1.4474 (18)
O1—N2	1.2423 (15)	C9—H9	0.9300
O2—N2	1.2549 (15)	C10—C11	1.5348 (18)
N1—C12	1.3711 (17)	C11—H11A	0.9700
N1—C11	1.4790 (17)	C11—H11B	0.9700
N1—H10	0.830 (18)	C12—C13	1.4292 (18)
N2—C17	1.4471 (17)	C12—C17	1.4346 (18)
C1—C2	1.435 (2)	C13—C14	1.3926 (19)
C1—C5	1.453 (2)	C13—H13	0.9300
C1—H1	0.9300	C14—C15	1.4096 (19)
C2—C3	1.445 (2)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.3790 (19)
C3—C4	1.449 (2)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.4179 (19)
C4—C5	1.432 (2)	C16—H16	0.9300

C3—Fe—C6	174.23 (6)	Fe—C3—H3	125.6
C3—Fe—C10	142.98 (6)	C5—C4—C3	107.29 (13)
C6—Fe—C10	41.54 (5)	C5—C4—Fe	70.17 (8)
C3—Fe—C9	112.44 (6)	C3—C4—Fe	68.56 (8)
C6—Fe—C9	68.95 (5)	C5—C4—H4	126.4
C10—Fe—C9	41.13 (5)	C3—C4—H4	126.4
C3—Fe—C4	41.26 (6)	Fe—C4—H4	126.5
C6—Fe—C4	144.34 (6)	C4—C5—C1	108.18 (13)
C10—Fe—C4	111.60 (6)	C4—C5—Fe	69.41 (7)
C9—Fe—C4	107.04 (6)	C1—C5—Fe	69.55 (7)
C3—Fe—C2	41.13 (6)	C4—C5—H5	125.9
C6—Fe—C2	134.76 (6)	C1—C5—H5	125.9
C10—Fe—C2	174.42 (5)	Fe—C5—H5	126.7
C9—Fe—C2	144.32 (6)	C7—C6—C10	109.39 (11)
C4—Fe—C2	69.45 (6)	C7—C6—Fe	70.56 (7)
C3—Fe—C8	108.74 (6)	C10—C6—Fe	69.27 (7)
C6—Fe—C8	68.34 (5)	C7—C6—H6	125.3
C10—Fe—C8	69.41 (5)	C10—C6—H6	125.3
C9—Fe—C8	41.27 (5)	Fe—C6—H6	126.5
C4—Fe—C8	132.87 (6)	C8—C7—C6	107.01 (12)
C2—Fe—C8	114.18 (5)	C8—C7—Fe	69.43 (7)
C3—Fe—C5	68.49 (6)	C6—C7—Fe	68.52 (7)
C6—Fe—C5	115.06 (6)	C8—C7—H7	126.5
C10—Fe—C5	108.15 (5)	C6—C7—H7	126.5
C9—Fe—C5	132.24 (6)	Fe—C7—H7	127.1
C4—Fe—C5	40.42 (6)	C7—C8—C9	108.81 (12)
C2—Fe—C5	68.87 (6)	C7—C8—Fe	70.09 (7)
C8—Fe—C5	172.26 (6)	C9—C8—Fe	69.00 (7)
C3—Fe—C1	68.33 (6)	C7—C8—H8	125.6
C6—Fe—C1	111.03 (5)	C9—C8—H8	125.6
C10—Fe—C1	134.27 (5)	Fe—C8—H8	126.9
C9—Fe—C1	172.94 (6)	C10—C9—C8	108.04 (12)
C4—Fe—C1	68.62 (6)	C10—C9—Fe	69.15 (7)
C2—Fe—C1	40.50 (6)	C8—C9—Fe	69.73 (7)
C8—Fe—C1	145.71 (6)	C10—C9—H9	126.0
C5—Fe—C1	40.94 (6)	C8—C9—H9	126.0
C3—Fe—C7	133.71 (6)	Fe—C9—H9	126.7
C6—Fe—C7	40.92 (5)	C9—C10—C6	106.74 (11)
C10—Fe—C7	69.88 (5)	C9—C10—C11	127.06 (12)
C9—Fe—C7	69.22 (5)	C6—C10—C11	126.19 (11)
C4—Fe—C7	172.91 (5)	C9—C10—Fe	69.71 (7)
C2—Fe—C7	109.79 (6)	C6—C10—Fe	69.19 (7)
C8—Fe—C7	40.49 (5)	C11—C10—Fe	125.33 (8)
C5—Fe—C7	146.44 (6)	N1—C11—C10	113.36 (10)
C1—Fe—C7	115.69 (6)	N1—C11—H11A	108.9
C12—N1—C11	125.30 (12)	C10—C11—H11A	108.9
C12—N1—H10	116.2 (13)	N1—C11—H11B	108.9
C11—N1—H10	118.1 (13)	C10—C11—H11B	108.9
O1—N2—O2	121.78 (12)	H11A—C11—H11B	107.7
O1—N2—C17	118.86 (11)	N1—C12—C13	121.41 (12)
O2—N2—C17	119.36 (11)	N1—C12—C17	123.88 (12)
C2—C1—C5	108.55 (12)	C13—C12—C17	114.71 (11)
C2—C1—Fe	69.43 (7)	C14—C13—C12	122.34 (12)
C5—C1—Fe	69.51 (7)	C14—C13—H13	118.8
C2—C1—H1	125.7	C12—C13—H13	118.8
C5—C1—H1	125.7	C13—C14—C15	121.41 (12)
Fe—C1—H1	126.9	C13—C14—H14	119.3
C1—C2—C3	107.00 (13)	C15—C14—H14	119.3
C1—C2—Fe	70.07 (8)	C16—C15—C14	118.34 (12)
C3—C2—Fe	68.54 (8)	C16—C15—H15	120.8
C1—C2—H2	126.5	C14—C15—H15	120.8
C3—C2—H2	126.5	C15—C16—C17	120.91 (12)
Fe—C2—H2	126.4	C15—C16—H16	119.5
C2—C3—C4	108.99 (12)	C17—C16—H16	119.5
C2—C3—Fe	70.33 (8)	C16—C17—C12	122.25 (12)
C4—C3—Fe	70.18 (8)	C16—C17—N2	116.03 (11)
C2—C3—H3	125.5	C12—C17—N2	121.70 (12)
C4—C3—H3	125.5

C3—Fe—C1—C2	−38.48 (9)	C3—Fe—C7—C8	−64.19 (11)
C6—Fe—C1—C2	135.36 (9)	C6—Fe—C7—C8	118.91 (11)
C10—Fe—C1—C2	177.19 (8)	C10—Fe—C7—C8	81.50 (8)
C4—Fe—C1—C2	−82.98 (10)	C9—Fe—C7—C8	37.47 (8)
C8—Fe—C1—C2	53.30 (14)	C2—Fe—C7—C8	−104.42 (9)
C5—Fe—C1—C2	−120.20 (12)	C5—Fe—C7—C8	174.23 (9)
C7—Fe—C1—C2	90.87 (9)	C1—Fe—C7—C8	−148.06 (8)
C3—Fe—C1—C5	81.72 (9)	C3—Fe—C7—C6	176.90 (8)
C6—Fe—C1—C5	−104.44 (9)	C10—Fe—C7—C6	−37.40 (7)
C10—Fe—C1—C5	−62.61 (11)	C9—Fe—C7—C6	−81.44 (8)
C4—Fe—C1—C5	37.21 (9)	C2—Fe—C7—C6	136.67 (8)
C2—Fe—C1—C5	120.20 (12)	C8—Fe—C7—C6	−118.91 (11)
C8—Fe—C1—C5	173.50 (9)	C5—Fe—C7—C6	55.33 (13)
C7—Fe—C1—C5	−148.93 (8)	C1—Fe—C7—C6	93.04 (8)
C5—C1—C2—C3	0.17 (15)	C6—C7—C8—C9	0.16 (14)
Fe—C1—C2—C3	58.82 (9)	Fe—C7—C8—C9	−58.25 (9)
C5—C1—C2—Fe	−58.65 (9)	C6—C7—C8—Fe	58.42 (8)
C3—Fe—C2—C1	118.47 (12)	C3—Fe—C8—C7	136.60 (9)
C6—Fe—C2—C1	−67.47 (11)	C6—Fe—C8—C7	−38.09 (8)
C9—Fe—C2—C1	171.60 (9)	C10—Fe—C8—C7	−82.77 (8)
C4—Fe—C2—C1	80.77 (9)	C9—Fe—C8—C7	−120.43 (11)
C8—Fe—C2—C1	−150.32 (9)	C4—Fe—C8—C7	176.41 (8)
C5—Fe—C2—C1	37.38 (9)	C2—Fe—C8—C7	92.62 (9)
C7—Fe—C2—C1	−106.74 (9)	C1—Fe—C8—C7	57.81 (13)
C6—Fe—C2—C3	174.06 (8)	C3—Fe—C8—C9	−102.97 (9)
C9—Fe—C2—C3	53.14 (13)	C6—Fe—C8—C9	82.34 (8)
C4—Fe—C2—C3	−37.70 (8)	C10—Fe—C8—C9	37.66 (8)
C8—Fe—C2—C3	91.21 (9)	C4—Fe—C8—C9	−63.16 (11)
C5—Fe—C2—C3	−81.08 (9)	C2—Fe—C8—C9	−146.95 (8)
C1—Fe—C2—C3	−118.47 (12)	C1—Fe—C8—C9	178.24 (9)
C7—Fe—C2—C3	134.79 (8)	C7—Fe—C8—C9	120.43 (11)
C1—C2—C3—C4	−0.05 (15)	C7—C8—C9—C10	0.20 (14)
Fe—C2—C3—C4	59.75 (9)	Fe—C8—C9—C10	−58.72 (8)
C1—C2—C3—Fe	−59.79 (9)	C7—C8—C9—Fe	58.92 (9)
C10—Fe—C3—C2	174.00 (8)	C3—Fe—C9—C10	−147.17 (8)
C9—Fe—C3—C2	−149.68 (8)	C6—Fe—C9—C10	38.87 (8)
C4—Fe—C3—C2	119.75 (11)	C4—Fe—C9—C10	−103.56 (8)
C8—Fe—C3—C2	−105.61 (9)	C2—Fe—C9—C10	178.13 (9)
C5—Fe—C3—C2	82.08 (9)	C8—Fe—C9—C10	119.60 (11)
C1—Fe—C3—C2	37.90 (8)	C5—Fe—C9—C10	−66.42 (10)
C7—Fe—C3—C2	−67.50 (10)	C7—Fe—C9—C10	82.82 (8)
C10—Fe—C3—C4	54.25 (12)	C3—Fe—C9—C8	93.23 (9)
C9—Fe—C3—C4	90.58 (8)	C6—Fe—C9—C8	−80.73 (8)
C2—Fe—C3—C4	−119.75 (11)	C10—Fe—C9—C8	−119.60 (11)
C8—Fe—C3—C4	134.64 (8)	C4—Fe—C9—C8	136.84 (8)
C5—Fe—C3—C4	−37.66 (8)	C2—Fe—C9—C8	58.53 (13)
C1—Fe—C3—C4	−81.85 (9)	C5—Fe—C9—C8	173.98 (8)
C7—Fe—C3—C4	172.75 (7)	C7—Fe—C9—C8	−36.78 (8)
C2—C3—C4—C5	−0.10 (15)	C8—C9—C10—C6	−0.48 (13)
Fe—C3—C4—C5	59.74 (9)	Fe—C9—C10—C6	−59.56 (8)
C2—C3—C4—Fe	−59.84 (9)	C8—C9—C10—C11	178.65 (11)
C3—Fe—C4—C5	−118.75 (12)	Fe—C9—C10—C11	119.57 (12)
C6—Fe—C4—C5	58.96 (13)	C8—C9—C10—Fe	59.08 (9)
C10—Fe—C4—C5	92.96 (9)	C7—C6—C10—C9	0.59 (14)
C9—Fe—C4—C5	136.42 (8)	Fe—C6—C10—C9	59.89 (8)
C2—Fe—C4—C5	−81.17 (9)	C7—C6—C10—C11	−178.55 (11)
C8—Fe—C4—C5	174.41 (8)	Fe—C6—C10—C11	−119.25 (12)
C1—Fe—C4—C5	−37.67 (9)	C7—C6—C10—Fe	−59.30 (9)
C6—Fe—C4—C3	177.71 (8)	C3—Fe—C10—C9	56.33 (12)
C10—Fe—C4—C3	−148.29 (8)	C6—Fe—C10—C9	−117.97 (11)
C9—Fe—C4—C3	−104.83 (8)	C4—Fe—C10—C9	91.48 (8)
C2—Fe—C4—C3	37.58 (8)	C8—Fe—C10—C9	−37.78 (8)
C8—Fe—C4—C3	−66.84 (11)	C5—Fe—C10—C9	134.43 (8)
C5—Fe—C4—C3	118.75 (12)	C1—Fe—C10—C9	172.19 (8)
C1—Fe—C4—C3	81.08 (9)	C7—Fe—C10—C9	−81.10 (8)
C3—C4—C5—C1	0.21 (15)	C3—Fe—C10—C6	174.30 (8)
Fe—C4—C5—C1	58.93 (9)	C9—Fe—C10—C6	117.97 (11)
C3—C4—C5—Fe	−58.72 (9)	C4—Fe—C10—C6	−150.56 (7)
C2—C1—C5—C4	−0.24 (15)	C8—Fe—C10—C6	80.18 (8)
Fe—C1—C5—C4	−58.84 (9)	C5—Fe—C10—C6	−107.60 (8)
C2—C1—C5—Fe	58.60 (9)	C1—Fe—C10—C6	−69.85 (10)
C3—Fe—C5—C4	38.42 (9)	C7—Fe—C10—C6	36.87 (7)
C6—Fe—C5—C4	−146.53 (9)	C3—Fe—C10—C11	−65.38 (14)
C10—Fe—C5—C4	−102.28 (9)	C6—Fe—C10—C11	120.33 (14)
C9—Fe—C5—C4	−62.91 (11)	C9—Fe—C10—C11	−121.71 (14)
C2—Fe—C5—C4	82.72 (9)	C4—Fe—C10—C11	−30.23 (12)
C1—Fe—C5—C4	119.71 (12)	C8—Fe—C10—C11	−159.49 (12)
C7—Fe—C5—C4	176.98 (10)	C5—Fe—C10—C11	12.73 (12)
C3—Fe—C5—C1	−81.29 (9)	C1—Fe—C10—C11	50.48 (14)
C6—Fe—C5—C1	93.75 (9)	C7—Fe—C10—C11	157.20 (12)
C10—Fe—C5—C1	138.00 (8)	C12—N1—C11—C10	−79.74 (16)
C9—Fe—C5—C1	177.38 (8)	C9—C10—C11—N1	89.84 (16)
C4—Fe—C5—C1	−119.71 (12)	C6—C10—C11—N1	−91.19 (15)
C2—Fe—C5—C1	−36.99 (9)	Fe—C10—C11—N1	180.00 (9)
C7—Fe—C5—C1	57.26 (13)	C11—N1—C12—C13	−11.7 (2)
C10—Fe—C6—C7	120.67 (10)	C11—N1—C12—C17	168.50 (13)
C9—Fe—C6—C7	82.17 (8)	N1—C12—C13—C14	−177.79 (13)
C4—Fe—C6—C7	172.30 (8)	C17—C12—C13—C14	1.99 (19)
C2—Fe—C6—C7	−65.41 (10)	C12—C13—C14—C15	−1.9 (2)
C8—Fe—C6—C7	37.70 (8)	C13—C14—C15—C16	0.0 (2)
C5—Fe—C6—C7	−149.87 (8)	C14—C15—C16—C17	1.7 (2)
C1—Fe—C6—C7	−105.40 (8)	C15—C16—C17—C12	−1.6 (2)
C9—Fe—C6—C10	−38.50 (7)	C15—C16—C17—N2	176.83 (13)
C4—Fe—C6—C10	51.63 (12)	N1—C12—C17—C16	179.49 (13)
C2—Fe—C6—C10	173.92 (7)	C13—C12—C17—C16	−0.3 (2)
C8—Fe—C6—C10	−82.97 (8)	N1—C12—C17—N2	1.2 (2)
C5—Fe—C6—C10	89.46 (8)	C13—C12—C17—N2	−178.58 (12)
C1—Fe—C6—C10	133.93 (8)	O1—N2—C17—C16	9.75 (19)
C7—Fe—C6—C10	−120.67 (10)	O2—N2—C17—C16	−169.57 (13)
C10—C6—C7—C8	−0.47 (14)	O1—N2—C17—C12	−171.86 (13)
Fe—C6—C7—C8	−58.99 (9)	O2—N2—C17—C12	8.8 (2)
C10—C6—C7—Fe	58.52 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H10···O2	0.827 (16)	2.01 (2)	2.6511 (19)	133.3 (18)
N1—H10···N2	0.827 (16)	2.624 (19)	2.961 (2)	106.0 (16)
C4—H4···O2ⁱ	0.93	2.57	3.283 (2)	134
C16—H16···O1	0.93	2.36	2.683 (2)	100

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₂H₁₁N₂O₂)]
M_r	336.17
Crystal system, space group	Monoclinic, P2₁/a
Temperature (K)	293
a, b, c (Å)	10.3609 (3), 7.8700 (2), 17.7948 (7)
β (°)	93.043 (2)
V (Å³)	1448.95 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.3 × 0.1 × 0.1

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14651, 3204, 2881
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.069, 1.05
No. of reflections	3204
No. of parameters	203
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.25

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H10···O2	0.827 (16)	2.01 (2)	2.6511 (19)	133.3 (18)
N1—H10···N2	0.827 (16)	2.624 (19)	2.961 (2)	106.0 (16)
C4—H4···O2ⁱ	0.93	2.5700	3.283 (2)	134.00

Symmetry code: (i) x, y+1, z.

Acknowledgements

This research was financed by the Laboratory of Valorization and Promotion of Saharan Resources (project No. E03220080002). The authors acknowledge the assistance of Merazig Hocine in the data collection.

References

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