Methyl (Sp)-2-(diphenyl­phosphino)ferrocene-1-carboxyl­ate

Štěpnička, P.; Tauchman, J.; Císařová, I.

doi:10.1107/S1600536809036654

metal-organic compounds

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Volume 65| Part 10| October 2009| Page m1216

doi:10.1107/S1600536809036654

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Methyl (S_p)-2-(diphenylphosphino)ferrocene-1-carboxylate

Petr Štěpnička,^a ^* Jiří Tauchman ^a and Ivana Císařová ^a

^aDepartment of Inorganic Chemistry, Faculty of Science, Charles University in Prague; Hlavova 2030, 12840 Prague 2, Czech Republic
^*Correspondence e-mail: stepnic@natur.cuni.cz

(Received 8 September 2009; accepted 10 September 2009; online 16 September 2009)

The title compound, [Fe(C₅H₅)(C₁₉H₁₆O₂P)], obtained serendipitously during recrystallization of 1-hydroxybenzotriazolyl (S_p)-2-(diphenylphosphino)ferrocene-1-carboxylate from methanol, crystallizes in the chiral space group P2₁2₁2₁. Its crystal structure not only confirms the anticipated absolute configuration but also establishes a rather regular geometry for the ferrocene unit, devoid of any significant deformation due to the attached substituents. In the crystal, symmetry-related molecules are linked via weak C—H⋯O interactions.

Related literature

For an overview of the chemistry of ferrocene, see: Štěpnička (2008 ). For the NMR spectroscopic data of the title compound, see: You et al. (2002 ); Lamač et al. (2008 ). For the structure of similar compounds, see: Lamač et al. (2009 ); Štěpnička (2002 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₉H₁₆O₂P)]
M_r = 428.23
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.6867 (2) Å
b = 12.9015 (3) Å
c = 14.1042 (2) Å
V = 1944.61 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.88 mm⁻¹
T = 150 K
0.40 × 0.40 × 0.28 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
15400 measured reflections
4449 independent reflections
4228 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.060
S = 1.06
4449 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 1918 Friedel pairs
Flack parameter: 0.004 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1ⁱ	0.93	2.58	3.184 (2)	123
C15—H15⋯O1ⁱⁱ	0.93	2.58	3.494 (3)	167
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+1]$ .

Data collection: COLLECT (Nonius, 2000 ); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036654/su2145sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036654/su2145Isup2.hkl

checkCIF report

Comment top

The crystal structure of the title compound was determined at 150 (2) K (Fig. 1). It crystallizes with the symmetry of the chiral space group P2₁2₁2₁ and one molecule in the asymmetric unit. The molecular geometry of the title compound compares well with the data reported previously for (S_p)-2-(diphenylphosphinoyl)ferrocene-1-carboxylic acid (Štěpnička, 2002) and methyl (R_p)-1',2-bis(diphenylphosphino)ferrocene-1-carboxylate (Lamač et al., 2009). The geometry of the ferrocene moiety is quite regular, showing similar Fe—ring centroid distances (1.6471 (9) and 1.6567 (9) Å for the rings C(1–5) and C(6–10), respectively) and insignificant tilting (the dihedral angle of the cyclopentadienyl mean planes being 2.08 (12) °). The attached substituents do not seem to impose any pronounced deformation of the ferrocene core, as evidenced by the C11—C1—C2—P torsion angle of –5.5 (3) °. However, the diphenylphosphinyl group binds somewhat unsymmetrically as indicated by the differences in the C(1/3)—C2—P angles being ca 2.7 ° (cf. the difference of the C(2/5)—C1—C11 angles, which is below 0.1 °, and also the perpendicular distances from the C(1–5) ring mean-plane: 0.136 (1) Å for P and –0.018 (2) Å for C11). This is reflected also by the variation in the Fe–C distances (2.0283 (18)–2.0672 (18) Å) for the substituted cyclopentadienyl ring (C1–C5).

The crystal structure of the title compound is essentially molecular, with symmetry related molecules forming only soft C—H···O contacts (Table 1).

Related literature top

For an overview of the chemistry of ferrocene, see: Štěpnička (2008). For the NMR spectroscopic data of the title compound, see: You et al. (2002); Lamač et al. (2008). For the structure of similar compounds, see: Lamač et al. (2009); Štěpnička (2002).

Experimental top

The title compound was formed on recrystallization of 1-hydroxybenzotriazolyl (S_p)-2-(diphenylphosphino)ferrocene-1-carboxylate (Štěpnička & Tauchman, unpublished results) from warm methanol, apparently resulting from a trans-esterification reaction of the starting activated ester. Its formulation was established by NMR spectroscopy (You et al., 2002; Lamač et al., 2008).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of the molecular structure of the title compound, showing the atom numbering scheme and displacement ellipsoids drawn at the 30% probability level.

Methyl (S_p)-2-(diphenylphosphino)ferrocene-1-carboxylate top

Crystal data top

[Fe(C₅H₅)(C₁₉H₁₆O₂P)]	F(000) = 888
M_r = 428.23	D_x = 1.463 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2517 reflections
a = 10.6867 (2) Å	θ = 1.0–27.5°
b = 12.9015 (3) Å	µ = 0.88 mm⁻¹
c = 14.1042 (2) Å	T = 150 K
V = 1944.61 (6) Å³	Block, orange
Z = 4	0.40 × 0.40 × 0.28 mm

Data collection top

Nonius KappaCCD diffractometer	4228 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Horizontally mounted graphite crystal monochromator	θ_max = 27.5°, θ_min = 2.1°
Detector resolution: 9.091 pixels mm^-1	h = −13→13
ω and π scans to fill the Ewald sphere	k = −16→16
15400 measured reflections	l = −18→18
4449 independent reflections

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)] = 0.025	H-atom parameters constrained
wR(F²) = 0.060	w = 1/[σ²(F_o²) + (0.0238P)² + 0.8124P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
4449 reflections	Δρ_max = 0.51 e Å⁻³
254 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1918 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.004 (11)

Crystal data top

[Fe(C₅H₅)(C₁₉H₁₆O₂P)]	V = 1944.61 (6) Å³
M_r = 428.23	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.6867 (2) Å	µ = 0.88 mm⁻¹
b = 12.9015 (3) Å	T = 150 K
c = 14.1042 (2) Å	0.40 × 0.40 × 0.28 mm

Data collection top

Nonius KappaCCD diffractometer	4228 reflections with I > 2σ(I)
15400 measured reflections	R_int = 0.036
4449 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	H-atom parameters constrained
wR(F²) = 0.060	Δρ_max = 0.51 e Å⁻³
S = 1.06	Δρ_min = −0.29 e Å⁻³
4449 reflections	Absolute structure: Flack (1983), 1918 Friedel pairs
254 parameters	Absolute structure parameter: 0.004 (11)
0 restraints

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	0.29965 (2)	0.18843 (2)	0.72459 (2)	0.0181 (1)
P1	0.09939 (4)	0.08083 (4)	0.56683 (3)	0.0184 (1)
O1	0.36618 (12)	0.01291 (12)	0.50125 (10)	0.0306 (4)
O2	0.53342 (11)	0.03569 (11)	0.59516 (9)	0.0268 (4)
C1	0.33684 (16)	0.04902 (14)	0.66438 (12)	0.0188 (5)
C2	0.20328 (18)	0.06630 (13)	0.66896 (11)	0.0184 (4)
C3	0.17351 (16)	0.07818 (15)	0.76755 (13)	0.0224 (5)
C4	0.28491 (19)	0.06905 (15)	0.82171 (12)	0.0252 (5)
C5	0.38563 (17)	0.05158 (14)	0.75918 (13)	0.0224 (5)
C6	0.40940 (19)	0.30253 (16)	0.66633 (14)	0.0273 (6)
C7	0.28422 (19)	0.31090 (16)	0.63399 (13)	0.0284 (5)
C8	0.20585 (19)	0.32594 (14)	0.71400 (16)	0.0318 (6)
C9	0.2832 (2)	0.32638 (16)	0.79572 (14)	0.0322 (6)
C10	0.40893 (18)	0.31174 (16)	0.76638 (14)	0.0284 (5)
C11	0.40972 (16)	0.03148 (13)	0.57782 (13)	0.0192 (5)
C12	0.04477 (16)	−0.05296 (14)	0.54954 (12)	0.0188 (5)
C13	−0.04839 (17)	−0.06903 (16)	0.48155 (12)	0.0221 (5)
C14	−0.09729 (19)	−0.16720 (16)	0.46657 (13)	0.0268 (5)
C15	−0.0535 (2)	−0.25121 (17)	0.51784 (15)	0.0304 (6)
C16	0.0408 (2)	−0.23636 (16)	0.58396 (15)	0.0308 (6)
C17	0.08946 (18)	−0.13788 (15)	0.59981 (14)	0.0249 (5)
C18	−0.04185 (16)	0.13315 (15)	0.62459 (13)	0.0215 (5)
C19	−0.0773 (2)	0.23452 (16)	0.60378 (15)	0.0305 (6)
C20	−0.1852 (2)	0.2765 (2)	0.64381 (16)	0.0438 (8)
C21	−0.2570 (2)	0.2184 (2)	0.70388 (16)	0.0431 (8)
C22	−0.22483 (18)	0.11714 (19)	0.72475 (16)	0.0371 (7)
C23	−0.11703 (17)	0.07494 (17)	0.68559 (14)	0.0278 (5)
C24	0.61344 (18)	0.01350 (18)	0.51607 (14)	0.0309 (6)
H3	0.09400	0.09000	0.79200	0.0270*
H4	0.29050	0.07380	0.88740	0.0300*
H5	0.46900	0.04320	0.77630	0.0270*
H6	0.47960	0.29270	0.62840	0.0330*
H7	0.25800	0.30720	0.57120	0.0340*
H8	0.11940	0.33400	0.71300	0.0380*
H9	0.25610	0.33480	0.85790	0.0390*
H10	0.47860	0.30870	0.80580	0.0340*
H13	−0.07780	−0.01340	0.44600	0.0270*
H14	−0.16000	−0.17670	0.42170	0.0320*
H15	−0.08690	−0.31690	0.50800	0.0360*
H16	0.07170	−0.29260	0.61790	0.0370*
H17	0.15250	−0.12880	0.64450	0.0300*
H19	−0.02870	0.27440	0.56300	0.0370*
H20	−0.20840	0.34430	0.62960	0.0530*
H21	−0.32830	0.24730	0.73100	0.0520*
H22	−0.27500	0.07760	0.76470	0.0450*
H23	−0.09470	0.00710	0.70020	0.0330*
H24A	0.61180	−0.05950	0.50310	0.0460*
H24B	0.69750	0.03430	0.53080	0.0460*
H24C	0.58460	0.05090	0.46140	0.0460*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0169 (1)	0.0204 (1)	0.0170 (1)	−0.0002 (1)	0.0003 (1)	−0.0020 (1)
P1	0.0167 (2)	0.0190 (2)	0.0196 (2)	−0.0010 (2)	−0.0012 (2)	0.0012 (2)
O1	0.0238 (7)	0.0435 (9)	0.0244 (6)	0.0042 (6)	−0.0028 (6)	−0.0110 (6)
O2	0.0157 (6)	0.0392 (8)	0.0256 (7)	0.0010 (6)	0.0011 (5)	−0.0030 (6)
C1	0.0189 (8)	0.0166 (9)	0.0210 (8)	0.0004 (7)	−0.0013 (7)	0.0004 (7)
C2	0.0173 (8)	0.0189 (8)	0.0190 (7)	−0.0036 (8)	−0.0004 (7)	0.0007 (6)
C3	0.0190 (8)	0.0273 (9)	0.0208 (8)	−0.0038 (7)	0.0048 (7)	0.0011 (8)
C4	0.0271 (9)	0.0311 (10)	0.0175 (8)	−0.0027 (8)	0.0000 (8)	0.0052 (7)
C5	0.0217 (8)	0.0231 (9)	0.0225 (9)	0.0013 (7)	−0.0042 (7)	0.0035 (7)
C6	0.0283 (10)	0.0227 (10)	0.0309 (9)	−0.0052 (9)	0.0065 (8)	0.0011 (8)
C7	0.0367 (10)	0.0191 (8)	0.0293 (9)	0.0027 (9)	−0.0063 (8)	0.0033 (8)
C8	0.0259 (9)	0.0198 (9)	0.0497 (12)	0.0048 (8)	−0.0013 (10)	−0.0072 (9)
C9	0.0371 (11)	0.0279 (10)	0.0316 (10)	−0.0041 (9)	0.0078 (9)	−0.0133 (8)
C10	0.0270 (9)	0.0267 (9)	0.0315 (9)	−0.0060 (9)	−0.0048 (8)	−0.0047 (9)
C11	0.0181 (8)	0.0152 (8)	0.0244 (8)	0.0025 (7)	−0.0003 (7)	0.0002 (7)
C12	0.0161 (8)	0.0224 (9)	0.0178 (8)	0.0000 (7)	0.0034 (6)	−0.0025 (7)
C13	0.0232 (8)	0.0250 (10)	0.0181 (8)	0.0009 (8)	0.0009 (7)	−0.0007 (7)
C14	0.0222 (8)	0.0321 (11)	0.0261 (9)	−0.0021 (8)	−0.0012 (8)	−0.0074 (8)
C15	0.0297 (10)	0.0238 (10)	0.0376 (12)	−0.0064 (8)	0.0043 (9)	−0.0061 (9)
C16	0.0337 (11)	0.0218 (10)	0.0370 (11)	0.0019 (8)	−0.0023 (9)	0.0028 (9)
C17	0.0253 (9)	0.0233 (9)	0.0261 (9)	−0.0001 (8)	−0.0031 (8)	−0.0003 (7)
C18	0.0160 (8)	0.0236 (9)	0.0250 (9)	0.0000 (7)	−0.0041 (7)	−0.0048 (7)
C19	0.0332 (11)	0.0276 (10)	0.0307 (10)	0.0077 (9)	−0.0088 (9)	−0.0023 (8)
C20	0.0474 (14)	0.0429 (13)	0.0412 (12)	0.0272 (12)	−0.0170 (11)	−0.0124 (10)
C21	0.0252 (10)	0.0666 (17)	0.0374 (12)	0.0200 (11)	−0.0078 (9)	−0.0214 (11)
C22	0.0213 (9)	0.0546 (14)	0.0354 (11)	−0.0048 (9)	0.0035 (9)	−0.0135 (11)
C23	0.0193 (8)	0.0300 (10)	0.0342 (10)	−0.0030 (8)	0.0033 (8)	−0.0073 (8)
C24	0.0201 (9)	0.0393 (12)	0.0332 (10)	0.0027 (8)	0.0069 (8)	−0.0014 (9)

Geometric parameters (Å, º) top

Fe1—C1	2.0283 (18)	C14—C15	1.384 (3)
Fe1—C2	2.0394 (17)	C15—C16	1.386 (3)
Fe1—C3	2.0512 (18)	C16—C17	1.391 (3)
Fe1—C4	2.0672 (18)	C18—C19	1.393 (3)
Fe1—C5	2.0493 (18)	C18—C23	1.396 (3)
Fe1—C6	2.054 (2)	C19—C20	1.394 (3)
Fe1—C7	2.039 (2)	C20—C21	1.367 (3)
Fe1—C8	2.0431 (19)	C21—C22	1.383 (4)
Fe1—C9	2.051 (2)	C22—C23	1.389 (3)
Fe1—C10	2.060 (2)	C3—H3	0.9300
P1—C2	1.8283 (18)	C4—H4	0.9300
P1—C12	1.8384 (19)	C5—H5	0.9300
P1—C18	1.8433 (18)	C6—H6	0.9300
O1—C11	1.200 (2)	C7—H7	0.9300
O2—C11	1.346 (2)	C8—H8	0.9300
O2—C24	1.434 (2)	C9—H9	0.9300
C1—C2	1.446 (3)	C10—H10	0.9300
C1—C5	1.436 (2)	C13—H13	0.9300
C1—C11	1.466 (2)	C14—H14	0.9300
C2—C3	1.435 (2)	C15—H15	0.9300
C3—C4	1.419 (3)	C16—H16	0.9300
C4—C5	1.410 (3)	C17—H17	0.9300
C6—C7	1.418 (3)	C19—H19	0.9300
C6—C10	1.416 (3)	C20—H20	0.9300
C7—C8	1.419 (3)	C21—H21	0.9300
C8—C9	1.418 (3)	C22—H22	0.9300
C9—C10	1.419 (3)	C23—H23	0.9300
C12—C13	1.398 (2)	C24—H24A	0.9600
C12—C17	1.390 (3)	C24—H24B	0.9600
C13—C14	1.386 (3)	C24—H24C	0.9600

C1—Fe1—C2	41.65 (7)	Fe1—C8—C9	70.01 (12)
C1—Fe1—C3	68.75 (7)	C7—C8—C9	107.63 (18)
C1—Fe1—C4	68.39 (7)	Fe1—C9—C8	69.45 (11)
C1—Fe1—C5	41.22 (7)	Fe1—C9—C10	70.15 (12)
C1—Fe1—C6	110.87 (8)	C8—C9—C10	108.33 (17)
C1—Fe1—C7	116.15 (7)	Fe1—C10—C6	69.64 (12)
C1—Fe1—C8	146.67 (8)	Fe1—C10—C9	69.47 (11)
C1—Fe1—C9	172.42 (8)	C6—C10—C9	107.77 (17)
C1—Fe1—C10	133.92 (7)	O1—C11—O2	123.54 (16)
C2—Fe1—C3	41.06 (7)	O1—C11—C1	125.06 (16)
C2—Fe1—C4	68.95 (7)	O2—C11—C1	111.37 (15)
C2—Fe1—C5	69.66 (7)	P1—C12—C13	117.16 (14)
C2—Fe1—C6	133.49 (7)	P1—C12—C17	124.29 (14)
C2—Fe1—C7	108.47 (7)	C13—C12—C17	118.55 (17)
C2—Fe1—C8	113.27 (8)	C12—C13—C14	120.57 (18)
C2—Fe1—C9	144.64 (8)	C13—C14—C15	120.55 (18)
C2—Fe1—C10	173.33 (7)	C14—C15—C16	119.3 (2)
C3—Fe1—C4	40.32 (7)	C15—C16—C17	120.41 (19)
C3—Fe1—C5	68.09 (7)	C12—C17—C16	120.64 (18)
C3—Fe1—C6	172.11 (8)	P1—C18—C19	118.26 (14)
C3—Fe1—C7	132.02 (8)	P1—C18—C23	123.13 (15)
C3—Fe1—C8	107.54 (8)	C19—C18—C23	118.58 (17)
C3—Fe1—C9	113.64 (8)	C18—C19—C20	120.3 (2)
C3—Fe1—C10	145.46 (8)	C19—C20—C21	120.2 (2)
C4—Fe1—C5	40.05 (7)	C20—C21—C22	120.7 (2)
C4—Fe1—C6	147.42 (8)	C21—C22—C23	119.5 (2)
C4—Fe1—C7	170.60 (8)	C18—C23—C22	120.8 (2)
C4—Fe1—C8	131.15 (8)	Fe1—C3—H3	127.00
C4—Fe1—C9	108.42 (8)	C2—C3—H3	125.00
C4—Fe1—C10	115.41 (8)	C4—C3—H3	125.00
C5—Fe1—C6	117.18 (8)	Fe1—C4—H4	127.00
C5—Fe1—C7	148.56 (8)	C3—C4—H4	126.00
C5—Fe1—C8	170.22 (8)	C5—C4—H4	126.00
C5—Fe1—C9	132.05 (8)	Fe1—C5—H5	126.00
C5—Fe1—C10	110.07 (8)	C1—C5—H5	126.00
C6—Fe1—C7	40.53 (8)	C4—C5—H5	126.00
C6—Fe1—C8	68.20 (8)	Fe1—C6—H6	126.00
C6—Fe1—C9	67.83 (8)	C7—C6—H6	126.00
C6—Fe1—C10	40.28 (8)	C10—C6—H6	126.00
C7—Fe1—C8	40.67 (8)	Fe1—C7—H7	126.00
C7—Fe1—C9	68.10 (8)	C6—C7—H7	126.00
C7—Fe1—C10	68.08 (8)	C8—C7—H7	126.00
C8—Fe1—C9	40.54 (8)	Fe1—C8—H8	126.00
C8—Fe1—C10	68.19 (8)	C7—C8—H8	126.00
C9—Fe1—C10	40.38 (8)	C9—C8—H8	126.00
C2—P1—C12	101.60 (8)	Fe1—C9—H9	126.00
C2—P1—C18	100.75 (8)	C8—C9—H9	126.00
C12—P1—C18	98.19 (8)	C10—C9—H9	126.00
C11—O2—C24	115.87 (14)	Fe1—C10—H10	126.00
Fe1—C1—C2	69.59 (10)	C6—C10—H10	126.00
Fe1—C1—C5	70.17 (10)	C9—C10—H10	126.00
Fe1—C1—C11	126.14 (13)	C12—C13—H13	120.00
C2—C1—C5	108.26 (15)	C14—C13—H13	120.00
C2—C1—C11	125.84 (15)	C13—C14—H14	120.00
C5—C1—C11	125.90 (16)	C15—C14—H14	120.00
Fe1—C2—P1	122.04 (9)	C14—C15—H15	120.00
Fe1—C2—C1	68.77 (10)	C16—C15—H15	120.00
Fe1—C2—C3	69.91 (10)	C15—C16—H16	120.00
P1—C2—C1	125.45 (12)	C17—C16—H16	120.00
P1—C2—C3	128.17 (14)	C12—C17—H17	120.00
C1—C2—C3	106.18 (15)	C16—C17—H17	120.00
Fe1—C3—C2	69.03 (10)	C18—C19—H19	120.00
Fe1—C3—C4	70.45 (11)	C20—C19—H19	120.00
C2—C3—C4	109.07 (15)	C19—C20—H20	120.00
Fe1—C4—C3	69.24 (11)	C21—C20—H20	120.00
Fe1—C4—C5	69.29 (10)	C20—C21—H21	120.00
C3—C4—C5	108.48 (15)	C22—C21—H21	120.00
Fe1—C5—C1	68.61 (10)	C21—C22—H22	120.00
Fe1—C5—C4	70.66 (11)	C23—C22—H22	120.00
C1—C5—C4	108.00 (16)	C18—C23—H23	120.00
Fe1—C6—C7	69.17 (12)	C22—C23—H23	120.00
Fe1—C6—C10	70.09 (12)	O2—C24—H24A	109.00
C7—C6—C10	108.11 (17)	O2—C24—H24B	109.00
Fe1—C7—C6	70.30 (12)	O2—C24—H24C	109.00
Fe1—C7—C8	69.83 (11)	H24A—C24—H24B	109.00
C6—C7—C8	108.16 (17)	H24A—C24—H24C	110.00
Fe1—C8—C7	69.50 (11)	H24B—C24—H24C	109.00

C2—Fe1—C1—C5	−119.32 (14)	C2—Fe1—C8—C9	149.66 (11)
C2—Fe1—C1—C11	120.12 (19)	C3—Fe1—C8—C7	−135.19 (12)
C3—Fe1—C1—C2	38.73 (10)	C3—Fe1—C8—C9	106.12 (12)
C3—Fe1—C1—C5	−80.58 (11)	C4—Fe1—C8—C7	−173.40 (11)
C3—Fe1—C1—C11	158.85 (17)	C4—Fe1—C8—C9	67.91 (15)
C4—Fe1—C1—C2	82.19 (11)	C6—Fe1—C8—C7	37.77 (12)
C4—Fe1—C1—C5	−37.13 (11)	C6—Fe1—C8—C9	−80.93 (13)
C4—Fe1—C1—C11	−157.69 (17)	C7—Fe1—C8—C9	−118.70 (17)
C5—Fe1—C1—C2	119.32 (14)	C9—Fe1—C8—C7	118.70 (17)
C5—Fe1—C1—C11	−120.57 (19)	C10—Fe1—C8—C7	81.30 (12)
C6—Fe1—C1—C2	−132.83 (10)	C10—Fe1—C8—C9	−37.40 (12)
C6—Fe1—C1—C5	107.86 (11)	C2—Fe1—C9—C8	−53.32 (18)
C6—Fe1—C1—C11	−12.71 (17)	C2—Fe1—C9—C10	−172.81 (12)
C7—Fe1—C1—C2	−88.80 (11)	C3—Fe1—C9—C8	−89.67 (13)
C7—Fe1—C1—C5	151.88 (11)	C3—Fe1—C9—C10	150.84 (11)
C7—Fe1—C1—C11	31.32 (17)	C4—Fe1—C9—C8	−132.66 (12)
C8—Fe1—C1—C2	−51.10 (17)	C4—Fe1—C9—C10	107.85 (12)
C8—Fe1—C1—C5	−170.41 (13)	C5—Fe1—C9—C8	−170.83 (12)
C8—Fe1—C1—C11	69.0 (2)	C5—Fe1—C9—C10	69.68 (15)
C10—Fe1—C1—C2	−172.79 (10)	C6—Fe1—C9—C8	81.92 (13)
C10—Fe1—C1—C5	67.89 (14)	C6—Fe1—C9—C10	−37.58 (12)
C10—Fe1—C1—C11	−52.67 (19)	C7—Fe1—C9—C8	38.04 (12)
C1—Fe1—C2—P1	−119.40 (15)	C7—Fe1—C9—C10	−81.46 (12)
C1—Fe1—C2—C3	117.41 (14)	C8—Fe1—C9—C10	−119.49 (17)
C3—Fe1—C2—P1	123.19 (16)	C10—Fe1—C9—C8	119.49 (17)
C3—Fe1—C2—C1	−117.41 (14)	C1—Fe1—C10—C6	68.19 (15)
C4—Fe1—C2—P1	159.87 (13)	C1—Fe1—C10—C9	−172.69 (11)
C4—Fe1—C2—C1	−80.73 (11)	C3—Fe1—C10—C6	−171.06 (13)
C4—Fe1—C2—C3	36.68 (11)	C3—Fe1—C10—C9	−51.93 (18)
C5—Fe1—C2—P1	−157.19 (13)	C4—Fe1—C10—C6	151.95 (12)
C5—Fe1—C2—C1	−37.79 (10)	C4—Fe1—C10—C9	−88.93 (13)
C5—Fe1—C2—C3	79.62 (11)	C5—Fe1—C10—C6	108.73 (12)
C6—Fe1—C2—P1	−48.55 (16)	C5—Fe1—C10—C9	−132.15 (12)
C6—Fe1—C2—C1	70.85 (13)	C6—Fe1—C10—C9	119.12 (17)
C6—Fe1—C2—C3	−171.74 (11)	C7—Fe1—C10—C6	−37.59 (12)
C7—Fe1—C2—P1	−10.52 (13)	C7—Fe1—C10—C9	81.53 (12)
C7—Fe1—C2—C1	108.88 (11)	C8—Fe1—C10—C6	−81.57 (13)
C7—Fe1—C2—C3	−133.71 (11)	C8—Fe1—C10—C9	37.55 (12)
C8—Fe1—C2—P1	32.86 (13)	C9—Fe1—C10—C6	−119.12 (17)
C8—Fe1—C2—C1	152.26 (11)	C12—P1—C2—Fe1	178.79 (10)
C8—Fe1—C2—C3	−90.33 (12)	C12—P1—C2—C1	93.31 (16)
C9—Fe1—C2—P1	67.43 (16)	C12—P1—C2—C3	−92.55 (17)
C9—Fe1—C2—C1	−173.17 (12)	C18—P1—C2—Fe1	−80.43 (12)
C9—Fe1—C2—C3	−55.76 (16)	C18—P1—C2—C1	−165.91 (15)
C1—Fe1—C3—C2	−39.27 (10)	C18—P1—C2—C3	8.23 (18)
C1—Fe1—C3—C4	81.23 (11)	C2—P1—C12—C13	173.55 (14)
C2—Fe1—C3—C4	120.50 (15)	C2—P1—C12—C17	−6.04 (18)
C4—Fe1—C3—C2	−120.50 (15)	C18—P1—C12—C13	70.72 (15)
C5—Fe1—C3—C2	−83.75 (11)	C18—P1—C12—C17	−108.86 (16)
C5—Fe1—C3—C4	36.75 (11)	C2—P1—C18—C19	113.07 (16)
C7—Fe1—C3—C2	67.35 (14)	C2—P1—C18—C23	−69.12 (17)
C7—Fe1—C3—C4	−172.15 (11)	C12—P1—C18—C19	−143.39 (16)
C8—Fe1—C3—C2	105.54 (12)	C12—P1—C18—C23	34.41 (17)
C8—Fe1—C3—C4	−133.96 (12)	C24—O2—C11—O1	−1.7 (3)
C9—Fe1—C3—C2	148.52 (11)	C24—O2—C11—C1	176.49 (16)
C9—Fe1—C3—C4	−90.98 (12)	Fe1—C1—C2—P1	114.97 (13)
C10—Fe1—C3—C2	−177.65 (13)	Fe1—C1—C2—C3	−60.24 (12)
C10—Fe1—C3—C4	−57.15 (17)	C5—C1—C2—Fe1	59.74 (12)
C1—Fe1—C4—C3	−82.20 (11)	C5—C1—C2—P1	174.71 (13)
C1—Fe1—C4—C5	38.18 (11)	C5—C1—C2—C3	−0.5 (2)
C2—Fe1—C4—C3	−37.33 (11)	C11—C1—C2—Fe1	−120.49 (18)
C2—Fe1—C4—C5	83.05 (11)	C11—C1—C2—P1	−5.5 (3)
C3—Fe1—C4—C5	120.38 (15)	C11—C1—C2—C3	179.27 (17)
C5—Fe1—C4—C3	−120.38 (15)	Fe1—C1—C5—C4	59.91 (13)
C6—Fe1—C4—C3	−177.45 (14)	C2—C1—C5—Fe1	−59.37 (12)
C6—Fe1—C4—C5	−57.07 (18)	C2—C1—C5—C4	0.5 (2)
C8—Fe1—C4—C3	65.71 (14)	C11—C1—C5—Fe1	120.86 (18)
C8—Fe1—C4—C5	−173.91 (11)	C11—C1—C5—C4	−179.23 (17)
C9—Fe1—C4—C3	105.12 (12)	Fe1—C1—C11—O1	−102.1 (2)
C9—Fe1—C4—C5	−134.50 (11)	Fe1—C1—C11—O2	79.71 (18)
C10—Fe1—C4—C3	148.17 (11)	C2—C1—C11—O1	−12.5 (3)
C10—Fe1—C4—C5	−91.45 (12)	C2—C1—C11—O2	169.40 (16)
C1—Fe1—C5—C4	−119.29 (15)	C5—C1—C11—O1	167.28 (19)
C2—Fe1—C5—C1	38.17 (10)	C5—C1—C11—O2	−10.9 (2)
C2—Fe1—C5—C4	−81.13 (11)	Fe1—C2—C3—C4	−59.22 (13)
C3—Fe1—C5—C1	82.31 (11)	P1—C2—C3—Fe1	−115.54 (14)
C3—Fe1—C5—C4	−36.99 (11)	P1—C2—C3—C4	−174.76 (14)
C4—Fe1—C5—C1	119.29 (15)	C1—C2—C3—Fe1	59.50 (12)
C6—Fe1—C5—C1	−91.24 (12)	C1—C2—C3—C4	0.3 (2)
C6—Fe1—C5—C4	149.47 (11)	Fe1—C3—C4—C5	−58.30 (13)
C7—Fe1—C5—C1	−54.20 (18)	C2—C3—C4—Fe1	58.35 (13)
C7—Fe1—C5—C4	−173.49 (14)	C2—C3—C4—C5	0.1 (2)
C9—Fe1—C5—C1	−175.02 (11)	Fe1—C4—C5—C1	−58.63 (13)
C9—Fe1—C5—C4	65.68 (14)	C3—C4—C5—Fe1	58.27 (13)
C10—Fe1—C5—C1	−134.72 (11)	C3—C4—C5—C1	−0.4 (2)
C10—Fe1—C5—C4	105.98 (12)	Fe1—C6—C7—C8	59.81 (14)
C1—Fe1—C6—C7	106.25 (12)	C10—C6—C7—Fe1	−59.48 (14)
C1—Fe1—C6—C10	−134.30 (11)	C10—C6—C7—C8	0.3 (2)
C2—Fe1—C6—C7	64.04 (15)	Fe1—C6—C10—C9	−59.21 (14)
C2—Fe1—C6—C10	−176.51 (11)	C7—C6—C10—Fe1	58.91 (14)
C4—Fe1—C6—C7	−171.54 (13)	C7—C6—C10—C9	−0.3 (2)
C4—Fe1—C6—C10	−52.09 (19)	Fe1—C7—C8—C9	59.88 (14)
C5—Fe1—C6—C7	151.09 (11)	C6—C7—C8—Fe1	−60.11 (14)
C5—Fe1—C6—C10	−89.47 (13)	C6—C7—C8—C9	−0.2 (2)
C7—Fe1—C6—C10	119.45 (17)	Fe1—C8—C9—C10	59.59 (14)
C8—Fe1—C6—C7	−37.90 (12)	C7—C8—C9—Fe1	−59.56 (13)
C8—Fe1—C6—C10	81.55 (13)	C7—C8—C9—C10	0.0 (2)
C9—Fe1—C6—C7	−81.78 (12)	Fe1—C9—C10—C6	59.32 (14)
C9—Fe1—C6—C10	37.67 (12)	C8—C9—C10—Fe1	−59.15 (14)
C10—Fe1—C6—C7	−119.45 (17)	C8—C9—C10—C6	0.2 (2)
C1—Fe1—C7—C6	−92.09 (12)	P1—C12—C13—C14	−177.91 (14)
C1—Fe1—C7—C8	148.96 (11)	C17—C12—C13—C14	1.7 (3)
C2—Fe1—C7—C6	−136.55 (11)	P1—C12—C17—C16	178.41 (15)
C2—Fe1—C7—C8	104.49 (12)	C13—C12—C17—C16	−1.2 (3)
C3—Fe1—C7—C6	−176.28 (11)	C12—C13—C14—C15	−0.9 (3)
C3—Fe1—C7—C8	64.77 (15)	C13—C14—C15—C16	−0.6 (3)
C5—Fe1—C7—C6	−55.55 (19)	C14—C15—C16—C17	1.1 (3)
C5—Fe1—C7—C8	−174.50 (14)	C15—C16—C17—C12	−0.2 (3)
C6—Fe1—C7—C8	−118.95 (16)	P1—C18—C19—C20	178.32 (16)
C8—Fe1—C7—C6	118.95 (16)	C23—C18—C19—C20	0.4 (3)
C9—Fe1—C7—C6	81.04 (13)	P1—C18—C23—C22	−177.83 (16)
C9—Fe1—C7—C8	−37.92 (12)	C19—C18—C23—C22	0.0 (3)
C10—Fe1—C7—C6	37.36 (11)	C18—C19—C20—C21	0.0 (3)
C10—Fe1—C7—C8	−81.59 (12)	C19—C20—C21—C22	−0.9 (3)
C1—Fe1—C8—C7	−57.39 (18)	C20—C21—C22—C23	1.3 (3)
C1—Fe1—C8—C9	−176.09 (13)	C21—C22—C23—C18	−0.8 (3)
C2—Fe1—C8—C7	−91.65 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.93	2.58	3.184 (2)	123
C15—H15···O1ⁱⁱ	0.93	2.58	3.494 (3)	167

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

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₉H₁₆O₂P)]
M_r	428.23
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	150
a, b, c (Å)	10.6867 (2), 12.9015 (3), 14.1042 (2)
V (Å³)	1944.61 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.88
Crystal size (mm)	0.40 × 0.40 × 0.28

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15400, 4449, 4228
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.060, 1.06
No. of reflections	4449
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.29
Absolute structure	Flack (1983), 1918 Friedel pairs
Absolute structure parameter	0.004 (11)

Computer programs: COLLECT (Nonius, 2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.93	2.58	3.184 (2)	123
C15—H15···O1ⁱⁱ	0.93	2.58	3.494 (3)	167

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

Acknowledgements

This work was supported financially by the Grant Agency of Charles University in Prague (project No. 58009) and is a part of the long-term research project supported by the Ministry of Education, Youth and Sports of the Czech Republic (project No. MSM0021620857).

References

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