2-Ferrocenyl-3-nitro-2H-chromene

Paramasivam, S.; Naga Siva Rao, J.; Seshadri, P.R.; Raghunathan, R.

doi:10.1107/S1600536813015730

2-Ferrocenyl-3-nitro-2H-chromene

S. Paramasivam, J. Naga Siva Rao, P. R. Seshadri and R. Raghunathan

In the title compound, [Fe(C₅H₅)(C₁₄H₁₀NO₃)], the cyclopentadienyl rings are in an eclipsed conformation and the pyran ring adopts a half-chair conformation. The mean plane of the pyran ring makes dihedral angles of 79.33 (1) and 80.73 (1)°, respectively, with the substituted and unsubstituted cyclopentadienyl rings. In the crystal, pairs of C—H

O hydrogen bonds link the molecules into inversion dimers with R₂²(16) motifs.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536813015730/is5279sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536813015730/is5279Isup2.hkl Contains datablock I

CCDC reference: 961528

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.028
wR factor = 0.076
Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ? Do !
PLAT153_ALERT_1_G The su's on the Cell Axes   are Equal ..........    0.00500 Ang.
PLAT793_ALERT_4_G The Model has Chirality at C9      (Verify) ....          S
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         25

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

As a continuation of our research related to ferrocenyl derivatives, we analyzed the crystal structure of (E)-1-ferrocenyl-3-[2-(2-hydroxyethoxy)phenyl]prop-2-en-1-one (Paramasivam et al., 2013). The present compound exhibits the pronounced similarity to the previous ones, either in bond lengths and angles as well as in molecular conformation.

Ferrocenyl derivatives exhibit antibacterial (Fouda et al., 2007), antitumor (Jaouen et al., 2004), antifungal and antimalarial (Biot et al., 2004) activities. It was proved that the replacement of the aromatic group by the ferrocenyl moiety in penicillins and cephalosporins could improve their antibiotic activity (Edwards et al., 1975). Against this background, the title compound was chosen for X-ray structure analysis (Fig. 1).

In the title compound, the pyran ring (O1/C1/C6–C9) adopts a half-chair conformation with the puckering parameters (Cremer & Pople, 1975) being q2 = 0.304 (1) Å, q3 = -0.138 (1) Å, QT = 0.334 (1) Å and it makes dihedral angles of 79.66 (1) and 80.65 (1)°, respectively, with the substituted (C10–C14) and unsubstituted (C15–C19) cyclopentadienyl (Cp) rings of the ferrocenyl unit. In ferrocenyl unit, the two Cp rings are planar and are essentially parallel to each other with a dihedral angle of 2.08 (1)° between them. The Fe atom lies in the middle of the two planes of Cp rings. The distances of the Fe1 atom from the centroids of the substituted and unsubstituted cyclopentadienyl rings are 1.636 (13) and 1.646 (14) Å, respectively. The Cg1—Fe1—Cg2 angle is 178.09 (4)°, where Cg1 and Cg2 are the centroids of (C10–C14) and (C15–C19) Cp rings, respectively. The C—C bond distances in the Cp rings range from 1.403 (3) to 1.429 (2) Å, while Fe—C bond lengths range between 2.028 (1) and 2.040 (2) Å and all of which are as expected (Zora et al., 2006). The torsion angles O1—C9—C10—C14 and C7—C8—N1—O2 [-42.8 (1)° and -6.1 (2)°, respectively] indicate the bent conformation of the molecule. The geometric parameters of the title compound (Fig. 1) agree well with the reported similar structures (Paramasivam et al., 2013).

The crystal packing reveals a weak C—H···O hydrogen bonds (Fig. 2). In the crystal structure, the molecules at (-x + 2, -y, -z + 1) are linked by C16—H16···O3 hydrogen bond, generating a centrosymmetric dimeric ring motif R₂²(16) (Bernstein et al., 1995).

Related literature top

For the biological activity of ferrocenyl derivatives, see: Fouda et al. (2007); Jaouen et al. (2004); Biot et al. (2004); Edwards et al. (1975). For conformational analysis and puckering parameters, see: Cremer & Pople (1975). For related structures, see: Zora et al. (2006); Paramasivam et al. (2013). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

To a solution of salicylaldehyde (2 equiv) and (E)-(2-nitrovinyl) ferrocene (1 equiv), 1,4 diazabicyclo[2.2.2]octane (DABCO) (0.5 equiv) was added, and in the absence of solvent the reaction mixture was stirred at 45 °C for 2 h. After completion of the reaction as indicated by TLC, the crude product was extracted with ethylacetate, The organic layer was dried with anhydrous sodium sulfate and concentrated in vacuo. Then the crude product was purified by column chromatography using hexane/EtOAc (9:1) as eluent.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The packing arrangement of the title compound viewed down c axis, showing the formation of centrosymmetric R₂²(16) dimer. The dashed lines indicate C—H···O intermolecular interactions. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry code: (i) -x +2, -y, -z + 1.]

2-Ferrocenyl-3-nitro-2H-chromene top

Crystal data top

[Fe(C₅H₅)(C₁₄H₁₀NO₃)]	F(000) = 744
M_r = 361.17	Monoclic
Monoclinic, P2₁/c	D_x = 1.530 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.047 (5) Å	Cell parameters from 3878 reflections
b = 19.317 (5) Å	θ = 2.0–28.3°
c = 8.135 (5) Å	µ = 0.98 mm⁻¹
β = 96.667 (5)°	T = 298 K
V = 1568.1 (13) Å³	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker SMART APEXII area-detector diffractometer	3878 independent reflections
Radiation source: fine-focus sealed tube	3320 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω and φ scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→13
T_min = 0.752, T_max = 0.822	k = −25→25
14295 measured reflections	l = −10→10

Refinement top

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)] = 0.028	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.033P)² + 0.4857P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3878 reflections	Δρ_max = 0.27 e Å⁻³
218 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0231 (10)

Crystal data top

[Fe(C₅H₅)(C₁₄H₁₀NO₃)]	V = 1568.1 (13) Å³
M_r = 361.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.047 (5) Å	µ = 0.98 mm⁻¹
b = 19.317 (5) Å	T = 298 K
c = 8.135 (5) Å	0.30 × 0.25 × 0.20 mm
β = 96.667 (5)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	3878 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3320 reflections with I > 2σ(I)
T_min = 0.752, T_max = 0.822	R_int = 0.032
14295 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.01	Δρ_max = 0.27 e Å⁻³
3878 reflections	Δρ_min = −0.27 e Å⁻³
218 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	0.86764 (2)	0.122593 (11)	0.36654 (3)	0.03932 (9)
O1	0.53463 (10)	0.08538 (5)	0.40784 (12)	0.0377 (2)
O3	0.67181 (11)	−0.10978 (6)	0.34443 (16)	0.0499 (3)
O2	0.48671 (13)	−0.13896 (6)	0.19888 (17)	0.0564 (3)
C8	0.52228 (13)	−0.02353 (7)	0.26407 (16)	0.0310 (3)
C7	0.41120 (13)	−0.00411 (7)	0.17099 (16)	0.0343 (3)
H7	0.3591	−0.0364	0.1077	0.041*
N1	0.56204 (12)	−0.09583 (6)	0.26937 (15)	0.0380 (3)
C1	0.43906 (14)	0.11112 (7)	0.28951 (18)	0.0358 (3)
C6	0.37266 (13)	0.06792 (7)	0.16975 (17)	0.0350 (3)
C10	0.73280 (13)	0.04854 (7)	0.28505 (16)	0.0334 (3)
C9	0.61296 (13)	0.02649 (7)	0.36567 (16)	0.0311 (3)
H9	0.6460	0.0031	0.4693	0.037*
C14	0.73990 (16)	0.10038 (8)	0.16104 (18)	0.0418 (3)
H14	0.6695	0.1279	0.1142	0.050*
C2	0.40451 (17)	0.18034 (9)	0.2994 (2)	0.0503 (4)
H2	0.4481	0.2087	0.3809	0.060*
C11	0.86294 (14)	0.01895 (8)	0.3209 (2)	0.0416 (3)
H11	0.8869	−0.0161	0.3971	0.050*
C5	0.27019 (15)	0.09517 (9)	0.0577 (2)	0.0459 (4)
H5	0.2245	0.0668	−0.0223	0.055*
C4	0.23676 (18)	0.16440 (10)	0.0658 (2)	0.0588 (5)
H4	0.1691	0.1827	−0.0094	0.071*
C13	0.87430 (18)	0.10230 (10)	0.1222 (2)	0.0540 (4)
H13	0.9071	0.1315	0.0454	0.065*
C3	0.3038 (2)	0.20631 (9)	0.1855 (3)	0.0612 (5)
H3	0.2809	0.2529	0.1897	0.073*
C16	1.02060 (19)	0.17053 (10)	0.5089 (3)	0.0621 (5)
H16	1.1114	0.1609	0.5098	0.074*
C19	0.8045 (2)	0.16867 (11)	0.5692 (3)	0.0644 (5)
H19	0.7277	0.1575	0.6172	0.077*
C12	0.94954 (16)	0.05243 (10)	0.2199 (2)	0.0538 (4)
H12	1.0402	0.0431	0.2184	0.065*
C15	0.9335 (2)	0.13943 (10)	0.6101 (2)	0.0625 (5)
H15	0.9564	0.1056	0.6898	0.075*
C18	0.8136 (2)	0.21766 (10)	0.4431 (3)	0.0651 (6)
H18	0.7437	0.2446	0.3932	0.078*
C17	0.9465 (2)	0.21885 (9)	0.4056 (3)	0.0650 (5)
H17	0.9798	0.2466	0.3264	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.03815 (13)	0.03059 (13)	0.04735 (14)	−0.00762 (8)	−0.00298 (9)	−0.00190 (9)
O1	0.0411 (5)	0.0328 (5)	0.0384 (5)	0.0026 (4)	0.0010 (4)	−0.0087 (4)
O3	0.0464 (6)	0.0370 (6)	0.0652 (7)	0.0085 (5)	0.0013 (5)	0.0051 (5)
O2	0.0640 (7)	0.0295 (6)	0.0730 (8)	−0.0069 (5)	−0.0030 (6)	−0.0103 (6)
C8	0.0352 (6)	0.0250 (6)	0.0334 (6)	−0.0023 (5)	0.0069 (5)	−0.0014 (5)
C7	0.0360 (6)	0.0327 (7)	0.0340 (6)	−0.0044 (5)	0.0037 (5)	−0.0034 (5)
N1	0.0439 (6)	0.0279 (6)	0.0430 (6)	0.0000 (5)	0.0084 (5)	−0.0001 (5)
C1	0.0362 (7)	0.0309 (7)	0.0415 (7)	0.0011 (5)	0.0093 (6)	0.0016 (6)
C6	0.0333 (6)	0.0347 (7)	0.0375 (7)	0.0009 (5)	0.0066 (5)	0.0027 (6)
C10	0.0364 (6)	0.0287 (7)	0.0345 (6)	−0.0050 (5)	0.0014 (5)	−0.0040 (5)
C9	0.0341 (6)	0.0265 (6)	0.0320 (6)	0.0002 (5)	0.0017 (5)	−0.0008 (5)
C14	0.0469 (8)	0.0400 (8)	0.0375 (7)	−0.0105 (6)	0.0002 (6)	0.0000 (6)
C2	0.0538 (9)	0.0317 (8)	0.0660 (10)	0.0031 (7)	0.0102 (8)	−0.0049 (7)
C11	0.0380 (7)	0.0324 (8)	0.0541 (8)	−0.0029 (6)	0.0036 (6)	−0.0054 (6)
C5	0.0397 (7)	0.0520 (10)	0.0455 (8)	0.0051 (7)	0.0032 (6)	0.0061 (7)
C4	0.0503 (9)	0.0566 (11)	0.0687 (11)	0.0174 (8)	0.0043 (8)	0.0200 (9)
C13	0.0576 (10)	0.0572 (11)	0.0495 (9)	−0.0189 (8)	0.0160 (8)	−0.0018 (8)
C3	0.0619 (10)	0.0364 (9)	0.0867 (13)	0.0153 (8)	0.0147 (10)	0.0118 (9)
C16	0.0506 (9)	0.0501 (11)	0.0791 (12)	−0.0092 (8)	−0.0194 (9)	−0.0113 (10)
C19	0.0669 (11)	0.0591 (12)	0.0667 (11)	−0.0139 (9)	0.0056 (9)	−0.0302 (10)
C12	0.0408 (8)	0.0514 (10)	0.0717 (11)	−0.0085 (7)	0.0167 (8)	−0.0104 (9)
C15	0.0843 (14)	0.0448 (10)	0.0527 (10)	−0.0026 (9)	−0.0159 (9)	−0.0089 (8)
C18	0.0631 (11)	0.0386 (9)	0.0864 (14)	0.0045 (8)	−0.0213 (10)	−0.0170 (10)
C17	0.0699 (12)	0.0370 (9)	0.0823 (13)	−0.0202 (8)	−0.0154 (10)	0.0009 (9)

Geometric parameters (Å, º) top

Fe1—C10	2.0280 (14)	C9—H9	0.9800
Fe1—C17	2.0315 (18)	C14—C13	1.423 (2)
Fe1—C14	2.0317 (17)	C14—H14	0.9300
Fe1—C18	2.0330 (19)	C2—C3	1.384 (3)
Fe1—C13	2.035 (2)	C2—H2	0.9300
Fe1—C11	2.0358 (16)	C11—C12	1.420 (2)
Fe1—C16	2.0364 (18)	C11—H11	0.9300
Fe1—C19	2.039 (2)	C5—C4	1.382 (3)
Fe1—C12	2.0407 (19)	C5—H5	0.9300
Fe1—C15	2.041 (2)	C4—C3	1.380 (3)
O1—C1	1.3715 (18)	C4—H4	0.9300
O1—C9	1.4471 (16)	C13—C12	1.411 (3)
O3—N1	1.2269 (17)	C13—H13	0.9300
O2—N1	1.2227 (17)	C3—H3	0.9300
C8—C7	1.328 (2)	C16—C15	1.404 (3)
C8—N1	1.4519 (18)	C16—C17	1.409 (3)
C8—C9	1.5072 (18)	C16—H16	0.9300
C7—C6	1.444 (2)	C19—C18	1.407 (3)
C7—H7	0.9300	C19—C15	1.417 (3)
C1—C2	1.386 (2)	C19—H19	0.9300
C1—C6	1.393 (2)	C12—H12	0.9300
C6—C5	1.397 (2)	C15—H15	0.9300
C10—C11	1.426 (2)	C18—C17	1.403 (3)
C10—C14	1.429 (2)	C18—H18	0.9300
C10—C9	1.4982 (19)	C17—H17	0.9300

C10—Fe1—C17	158.48 (7)	O1—C9—H9	107.4
C10—Fe1—C14	41.22 (6)	C10—C9—H9	107.4
C17—Fe1—C14	121.30 (7)	C8—C9—H9	107.4
C10—Fe1—C18	123.06 (7)	C13—C14—C10	107.55 (15)
C17—Fe1—C18	40.40 (9)	C13—C14—Fe1	69.64 (10)
C14—Fe1—C18	106.10 (8)	C10—C14—Fe1	69.25 (8)
C10—Fe1—C13	68.98 (6)	C13—C14—H14	126.2
C17—Fe1—C13	105.82 (8)	C10—C14—H14	126.2
C14—Fe1—C13	40.95 (7)	Fe1—C14—H14	126.5
C18—Fe1—C13	120.90 (9)	C3—C2—C1	118.63 (17)
C10—Fe1—C11	41.08 (6)	C3—C2—H2	120.7
C17—Fe1—C11	158.28 (8)	C1—C2—H2	120.7
C14—Fe1—C11	69.10 (7)	C12—C11—C10	107.93 (15)
C18—Fe1—C11	160.53 (8)	C12—C11—Fe1	69.80 (10)
C13—Fe1—C11	68.61 (7)	C10—C11—Fe1	69.17 (8)
C10—Fe1—C16	159.72 (7)	C12—C11—H11	126.0
C17—Fe1—C16	40.54 (8)	C10—C11—H11	126.0
C14—Fe1—C16	157.95 (8)	Fe1—C11—H11	126.6
C18—Fe1—C16	68.01 (8)	C4—C5—C6	119.88 (16)
C13—Fe1—C16	122.33 (9)	C4—C5—H5	120.1
C11—Fe1—C16	123.42 (7)	C6—C5—H5	120.1
C10—Fe1—C19	108.28 (7)	C3—C4—C5	119.99 (16)
C17—Fe1—C19	68.05 (9)	C3—C4—H4	120.0
C14—Fe1—C19	122.11 (8)	C5—C4—H4	120.0
C18—Fe1—C19	40.42 (9)	C12—C13—C14	108.49 (15)
C13—Fe1—C19	157.35 (9)	C12—C13—Fe1	69.96 (11)
C11—Fe1—C19	125.02 (8)	C14—C13—Fe1	69.41 (9)
C16—Fe1—C19	68.08 (9)	C12—C13—H13	125.8
C10—Fe1—C12	68.89 (7)	C14—C13—H13	125.8
C17—Fe1—C12	121.53 (9)	Fe1—C13—H13	126.5
C14—Fe1—C12	68.77 (8)	C4—C3—C2	121.23 (16)
C18—Fe1—C12	156.79 (9)	C4—C3—H3	119.4
C13—Fe1—C12	40.53 (8)	C2—C3—H3	119.4
C11—Fe1—C12	40.77 (7)	C15—C16—C17	108.10 (18)
C16—Fe1—C12	107.79 (8)	C15—C16—Fe1	70.02 (11)
C19—Fe1—C12	161.28 (9)	C17—C16—Fe1	69.54 (10)
C10—Fe1—C15	123.97 (8)	C15—C16—H16	126.0
C17—Fe1—C15	68.02 (9)	C17—C16—H16	126.0
C14—Fe1—C15	159.25 (8)	Fe1—C16—H16	126.1
C18—Fe1—C15	68.06 (8)	C18—C19—C15	107.68 (19)
C13—Fe1—C15	159.30 (9)	C18—C19—Fe1	69.57 (12)
C11—Fe1—C15	109.37 (7)	C15—C19—Fe1	69.75 (11)
C16—Fe1—C15	40.29 (9)	C18—C19—H19	126.2
C19—Fe1—C15	40.66 (9)	C15—C19—H19	126.2
C12—Fe1—C15	124.47 (9)	Fe1—C19—H19	126.1
C1—O1—C9	118.31 (11)	C13—C12—C11	108.23 (15)
C7—C8—N1	119.92 (12)	C13—C12—Fe1	69.51 (11)
C7—C8—C9	123.11 (13)	C11—C12—Fe1	69.43 (10)
N1—C8—C9	116.97 (11)	C13—C12—H12	125.9
C8—C7—C6	118.89 (13)	C11—C12—H12	125.9
C8—C7—H7	120.6	Fe1—C12—H12	126.8
C6—C7—H7	120.6	C16—C15—C19	107.89 (19)
O2—N1—O3	123.74 (13)	C16—C15—Fe1	69.68 (11)
O2—N1—C8	119.23 (13)	C19—C15—Fe1	69.60 (11)
O3—N1—C8	117.03 (12)	C16—C15—H15	126.1
O1—C1—C2	117.93 (14)	C19—C15—H15	126.1
O1—C1—C6	120.88 (13)	Fe1—C15—H15	126.2
C2—C1—C6	121.06 (14)	C17—C18—C19	108.30 (17)
C1—C6—C5	119.19 (14)	C17—C18—Fe1	69.75 (11)
C1—C6—C7	117.79 (12)	C19—C18—Fe1	70.02 (11)
C5—C6—C7	123.00 (14)	C17—C18—H18	125.8
C11—C10—C14	107.80 (13)	C19—C18—H18	125.8
C11—C10—C9	124.12 (13)	Fe1—C18—H18	126.0
C14—C10—C9	128.07 (13)	C18—C17—C16	108.03 (19)
C11—C10—Fe1	69.75 (8)	C18—C17—Fe1	69.86 (10)
C14—C10—Fe1	69.53 (8)	C16—C17—Fe1	69.92 (10)
C9—C10—Fe1	126.71 (10)	C18—C17—H17	126.0
O1—C9—C10	111.54 (11)	C16—C17—H17	126.0
O1—C9—C8	108.86 (11)	Fe1—C17—H17	125.8
C10—C9—C8	114.05 (11)

N1—C8—C7—C6	179.06 (12)	C1—C2—C3—C4	1.2 (3)
C9—C8—C7—C6	−1.8 (2)	C10—Fe1—C16—C15	−45.6 (3)
C7—C8—N1—O2	−6.1 (2)	C17—Fe1—C16—C15	119.24 (19)
C9—C8—N1—O2	174.62 (13)	C14—Fe1—C16—C15	160.02 (18)
C7—C8—N1—O3	173.14 (13)	C18—Fe1—C16—C15	81.56 (14)
C9—C8—N1—O3	−6.09 (18)	C13—Fe1—C16—C15	−164.86 (12)
C9—O1—C1—C2	−153.62 (13)	C11—Fe1—C16—C15	−80.57 (14)
C9—O1—C1—C6	30.53 (18)	C19—Fe1—C16—C15	37.83 (13)
O1—C1—C6—C5	176.06 (13)	C12—Fe1—C16—C15	−122.74 (13)
C2—C1—C6—C5	0.3 (2)	C10—Fe1—C16—C17	−164.87 (19)
O1—C1—C6—C7	−2.15 (19)	C14—Fe1—C16—C17	40.8 (3)
C2—C1—C6—C7	−177.87 (14)	C18—Fe1—C16—C17	−37.67 (14)
C8—C7—C6—C1	−12.08 (19)	C13—Fe1—C16—C17	75.90 (16)
C8—C7—C6—C5	169.79 (14)	C11—Fe1—C16—C17	160.19 (13)
C17—Fe1—C10—C11	160.9 (2)	C19—Fe1—C16—C17	−81.40 (15)
C14—Fe1—C10—C11	119.05 (13)	C12—Fe1—C16—C17	118.03 (14)
C18—Fe1—C10—C11	−164.87 (11)	C15—Fe1—C16—C17	−119.24 (19)
C13—Fe1—C10—C11	81.15 (11)	C10—Fe1—C19—C18	−119.88 (11)
C16—Fe1—C10—C11	−46.7 (2)	C17—Fe1—C19—C18	37.51 (11)
C19—Fe1—C10—C11	−122.75 (11)	C14—Fe1—C19—C18	−76.59 (13)
C12—Fe1—C10—C11	37.58 (10)	C13—Fe1—C19—C18	−40.8 (2)
C15—Fe1—C10—C11	−80.55 (12)	C11—Fe1—C19—C18	−162.33 (10)
C17—Fe1—C10—C14	41.8 (2)	C16—Fe1—C19—C18	81.38 (12)
C18—Fe1—C10—C14	76.08 (12)	C12—Fe1—C19—C18	162.08 (19)
C13—Fe1—C10—C14	−37.90 (10)	C15—Fe1—C19—C18	118.88 (17)
C11—Fe1—C10—C14	−119.05 (13)	C10—Fe1—C19—C15	121.24 (12)
C16—Fe1—C10—C14	−165.7 (2)	C17—Fe1—C19—C15	−81.37 (13)
C19—Fe1—C10—C14	118.20 (11)	C14—Fe1—C19—C15	164.53 (11)
C12—Fe1—C10—C14	−81.47 (11)	C18—Fe1—C19—C15	−118.88 (17)
C15—Fe1—C10—C14	160.40 (11)	C13—Fe1—C19—C15	−159.69 (18)
C17—Fe1—C10—C9	−81.0 (3)	C11—Fe1—C19—C15	78.79 (14)
C14—Fe1—C10—C9	−122.87 (16)	C16—Fe1—C19—C15	−37.50 (12)
C18—Fe1—C10—C9	−46.79 (15)	C12—Fe1—C19—C15	43.2 (3)
C13—Fe1—C10—C9	−160.77 (14)	C14—C13—C12—C11	−0.1 (2)
C11—Fe1—C10—C9	118.08 (16)	Fe1—C13—C12—C11	58.80 (12)
C16—Fe1—C10—C9	71.4 (3)	C14—C13—C12—Fe1	−58.89 (12)
C19—Fe1—C10—C9	−4.67 (14)	C10—C11—C12—C13	−0.01 (19)
C12—Fe1—C10—C9	155.66 (14)	Fe1—C11—C12—C13	−58.85 (13)
C15—Fe1—C10—C9	37.53 (15)	C10—C11—C12—Fe1	58.85 (11)
C1—O1—C9—C10	86.39 (14)	C10—Fe1—C12—C13	81.94 (10)
C1—O1—C9—C8	−40.33 (15)	C17—Fe1—C12—C13	−76.98 (12)
C11—C10—C9—O1	137.94 (13)	C14—Fe1—C12—C13	37.58 (10)
C14—C10—C9—O1	−42.85 (18)	C18—Fe1—C12—C13	−43.7 (2)
Fe1—C10—C9—O1	48.87 (15)	C11—Fe1—C12—C13	119.80 (14)
C11—C10—C9—C8	−98.24 (16)	C16—Fe1—C12—C13	−119.29 (11)
C14—C10—C9—C8	80.98 (18)	C19—Fe1—C12—C13	166.7 (2)
Fe1—C10—C9—C8	172.69 (10)	C15—Fe1—C12—C13	−160.58 (11)
C7—C8—C9—O1	26.80 (17)	C10—Fe1—C12—C11	−37.85 (9)
N1—C8—C9—O1	−153.99 (11)	C17—Fe1—C12—C11	163.23 (10)
C7—C8—C9—C10	−98.46 (16)	C14—Fe1—C12—C11	−82.21 (10)
N1—C8—C9—C10	80.76 (15)	C18—Fe1—C12—C11	−163.54 (16)
C11—C10—C14—C13	−0.15 (17)	C13—Fe1—C12—C11	−119.80 (14)
C9—C10—C14—C13	−179.46 (14)	C16—Fe1—C12—C11	120.92 (11)
Fe1—C10—C14—C13	59.33 (11)	C19—Fe1—C12—C11	46.9 (3)
C11—C10—C14—Fe1	−59.48 (10)	C15—Fe1—C12—C11	79.63 (13)
C9—C10—C14—Fe1	121.21 (14)	C17—C16—C15—C19	0.0 (2)
C10—Fe1—C14—C13	−118.98 (15)	Fe1—C16—C15—C19	−59.33 (13)
C17—Fe1—C14—C13	77.66 (14)	C17—C16—C15—Fe1	59.33 (13)
C18—Fe1—C14—C13	118.88 (13)	C18—C19—C15—C16	−0.1 (2)
C11—Fe1—C14—C13	−81.04 (11)	Fe1—C19—C15—C16	59.38 (13)
C16—Fe1—C14—C13	47.9 (2)	C18—C19—C15—Fe1	−59.46 (13)
C19—Fe1—C14—C13	159.90 (12)	C10—Fe1—C15—C16	162.62 (11)
C12—Fe1—C14—C13	−37.20 (11)	C17—Fe1—C15—C16	−37.71 (12)
C15—Fe1—C14—C13	−170.7 (2)	C14—Fe1—C15—C16	−158.78 (19)
C17—Fe1—C14—C10	−163.36 (11)	C18—Fe1—C15—C16	−81.42 (13)
C18—Fe1—C14—C10	−122.14 (11)	C13—Fe1—C15—C16	38.6 (3)
C13—Fe1—C14—C10	118.98 (15)	C11—Fe1—C15—C16	119.22 (12)
C11—Fe1—C14—C10	37.95 (9)	C19—Fe1—C15—C16	−119.15 (18)
C16—Fe1—C14—C10	166.84 (18)	C12—Fe1—C15—C16	76.30 (14)
C19—Fe1—C14—C10	−81.11 (12)	C10—Fe1—C15—C19	−78.22 (14)
C12—Fe1—C14—C10	81.78 (10)	C17—Fe1—C15—C19	81.44 (14)
C15—Fe1—C14—C10	−51.7 (2)	C14—Fe1—C15—C19	−39.6 (3)
O1—C1—C2—C3	−177.03 (15)	C18—Fe1—C15—C19	37.73 (12)
C6—C1—C2—C3	−1.2 (2)	C13—Fe1—C15—C19	157.8 (2)
C14—C10—C11—C12	0.10 (17)	C11—Fe1—C15—C19	−121.63 (12)
C9—C10—C11—C12	179.45 (13)	C16—Fe1—C15—C19	119.15 (18)
Fe1—C10—C11—C12	−59.24 (11)	C12—Fe1—C15—C19	−164.54 (11)
C14—C10—C11—Fe1	59.34 (10)	C15—C19—C18—C17	0.1 (2)
C9—C10—C11—Fe1	−121.31 (13)	Fe1—C19—C18—C17	−59.45 (13)
C10—Fe1—C11—C12	119.40 (14)	C15—C19—C18—Fe1	59.57 (13)
C17—Fe1—C11—C12	−41.7 (2)	C10—Fe1—C18—C17	−161.43 (11)
C14—Fe1—C11—C12	81.33 (12)	C14—Fe1—C18—C17	−119.68 (12)
C18—Fe1—C11—C12	160.4 (2)	C13—Fe1—C18—C17	−77.70 (13)
C13—Fe1—C11—C12	37.27 (11)	C11—Fe1—C18—C17	167.60 (19)
C16—Fe1—C11—C12	−78.18 (14)	C16—Fe1—C18—C17	37.81 (13)
C19—Fe1—C11—C12	−163.38 (11)	C19—Fe1—C18—C17	119.36 (16)
C15—Fe1—C11—C12	−120.73 (12)	C12—Fe1—C18—C17	−46.1 (2)
C17—Fe1—C11—C10	−161.06 (19)	C15—Fe1—C18—C17	81.41 (13)
C14—Fe1—C11—C10	−38.07 (9)	C10—Fe1—C18—C19	79.21 (13)
C18—Fe1—C11—C10	41.0 (3)	C17—Fe1—C18—C19	−119.36 (16)
C13—Fe1—C11—C10	−82.13 (10)	C14—Fe1—C18—C19	120.96 (12)
C16—Fe1—C11—C10	162.42 (10)	C13—Fe1—C18—C19	162.94 (11)
C19—Fe1—C11—C10	77.22 (12)	C11—Fe1—C18—C19	48.2 (3)
C12—Fe1—C11—C10	−119.40 (14)	C16—Fe1—C18—C19	−81.56 (13)
C15—Fe1—C11—C10	119.87 (10)	C12—Fe1—C18—C19	−165.48 (17)
C1—C6—C5—C4	0.6 (2)	C15—Fe1—C18—C19	−37.95 (12)
C7—C6—C5—C4	178.67 (15)	C19—C18—C17—C16	−0.1 (2)
C6—C5—C4—C3	−0.6 (3)	Fe1—C18—C17—C16	−59.73 (13)
C10—C14—C13—C12	0.15 (19)	C19—C18—C17—Fe1	59.62 (13)
Fe1—C14—C13—C12	59.23 (13)	C15—C16—C17—C18	0.1 (2)
C10—C14—C13—Fe1	−59.08 (11)	Fe1—C16—C17—C18	59.70 (13)
C10—Fe1—C13—C12	−81.71 (10)	C15—C16—C17—Fe1	−59.63 (13)
C17—Fe1—C13—C12	120.33 (11)	C10—Fe1—C17—C18	46.7 (3)
C14—Fe1—C13—C12	−119.85 (14)	C14—Fe1—C17—C18	77.66 (15)
C18—Fe1—C13—C12	161.48 (10)	C13—Fe1—C17—C18	119.39 (13)
C11—Fe1—C13—C12	−37.49 (9)	C11—Fe1—C17—C18	−168.85 (18)
C16—Fe1—C13—C12	79.39 (12)	C16—Fe1—C17—C18	−119.02 (19)
C19—Fe1—C13—C12	−168.93 (18)	C19—Fe1—C17—C18	−37.53 (12)
C15—Fe1—C13—C12	50.9 (3)	C12—Fe1—C17—C18	160.53 (12)
C10—Fe1—C13—C14	38.14 (10)	C15—Fe1—C17—C18	−81.53 (14)
C17—Fe1—C13—C14	−119.83 (11)	C10—Fe1—C17—C16	165.72 (18)
C18—Fe1—C13—C14	−78.67 (12)	C14—Fe1—C17—C16	−163.32 (12)
C11—Fe1—C13—C14	82.35 (10)	C18—Fe1—C17—C16	119.02 (19)
C16—Fe1—C13—C14	−160.76 (10)	C13—Fe1—C17—C16	−121.60 (14)
C19—Fe1—C13—C14	−49.1 (2)	C11—Fe1—C17—C16	−49.8 (3)
C12—Fe1—C13—C14	119.85 (14)	C19—Fe1—C17—C16	81.49 (15)
C15—Fe1—C13—C14	170.70 (19)	C12—Fe1—C17—C16	−80.45 (16)
C5—C4—C3—C2	−0.3 (3)	C15—Fe1—C17—C16	37.49 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O3ⁱ	0.93	2.55	3.390 (3)	150

Symmetry code: (i) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₄H₁₀NO₃)]
M_r	361.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.047 (5), 19.317 (5), 8.135 (5)
β (°)	96.667 (5)
V (Å³)	1568.1 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.98
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.752, 0.822
No. of measured, independent and observed [I > 2σ(I)] reflections	14295, 3878, 3320
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.076, 1.01
No. of reflections	3878
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.27

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O3ⁱ	0.93	2.55	3.390 (3)	150

Symmetry code: (i) −x+2, −y, −z+1.

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