1,2:5,6-Di-O-isopropyl­idene-α-d-3-glucofuranosyl (Rp)-2-(diphenyl­phosphino)ferrocene-1-carboxyl­ate

Štěpnička, P.; Lamač, M.; Císařová, I.

doi:10.1107/S1600536809038653

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages m1252-m1253

doi:10.1107/S1600536809038653

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1,2:5,6-Di-O-isopropylidene-α-D-3-glucofuranosyl (R_p)-2-(diphenylphosphino)ferrocene-1-carboxylate

Petr Štěpnička,^a ^* Martin Lamač ^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 24 September 2009; online 30 September 2009)

The title compound, [Fe(C₅H₅)(C₃₀H₃₂O₇P)], which is an intermediate in the synthesis of (R_p)-2-(diphenylphosphino)ferrocene-1-carboxylic acid, crystallizes in the common chiral space group P2₁2₁2₁. In general, the molecular geometry is very similar to that of the corresponding 2,1′-bis(diphenylphosphino) congener. The ferrocene unit assumes a regular geometry with the proximal bulky substituents efficiently avoiding mutual spatial contacts. In the crystal, the molecules participate in weak intra- and intermolecular C—H⋯O interactions.

Related literature

The title compound was prepared according to Breit & Breuninger (2005a ). For a related structure, see: Lamač et al. (2009 ). For selected references concerning the use of enantiopure 2-(diphenylphosphino)ferrocene-1-carboxylic acids, see: Longmire et al. (2000 , 2002 ); You et al. (2000 , 2001 ); Štěpnička (2002 ); Breit & Breuninger (2004 , 2005b ,c ); Lamač et al. (2007 ); Bianchini et al. (2008 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₃₀H₃₂O₇P)]
M_r = 656.47
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.3488 (1) Å
b = 11.5379 (1) Å
c = 26.9830 (3) Å
V = 3221.86 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.57 mm⁻¹
T = 150 K
0.30 × 0.20 × 0.18 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
68616 measured reflections
7369 independent reflections
6632 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.112
S = 1.07
7369 reflections
401 parameters
H-atom parameters constrained
Δρ_max = 2.00 e Å⁻³
Δρ_min = −0.41 e Å⁻³
Absolute structure: Flack (1983 ), 3230 Friedel pairs
Flack parameter: −0.012 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O34	0.93	2.50	3.357 (4)	153
C9—H9⋯O1ⁱ	0.93	2.54	3.314 (4)	140
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: 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: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038653/im2141sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809038653/im2141Isup2.hkl

checkCIF report

Comment top

1,2:5,6-Di-O-isopropylidene-α-D-3-glucofuranosyl 2-(diphenylphosphino)ferrocene-1-carboxylates are useful intermediates in the preparation of optically pure, planar-only chiral 2-(diphenylphosphino)ferrocene-1-carboxylic acids, which already proved to be valuable organometallic synthetic building blocks and chiral auxilliaries (selected references: Longmire et al., 2000 and 2002; You et al., 2000 and 2001; Štěpnička, 2002; Breit & Breuninger, 2004 and 2005b,c; Lamač et al., 2007; and Bianchini et al., 2008).

Structural parameters of the title compound (Fig. 1) are very similar to those reported previously for the related bisphosphine derivative, 1,2:5,6-di-O-isopropylidene-α-D-3-glucofuranosyl (R_p)-2,1'-bis(diphenylphosphino)ferrocene-1-carboxylate (Lamač et al., 2009). Likwise this reference compound, the ferrocene unit in the title compound is only negligibly tilted (dihedral angle of the mean cyclopentadienyl planes being 2.7 (2)°) and displays similar Fe—ring centroid distances (1.640 (1) and 1.650 (12) Å for the cyclopentadienyl rings C(1–5) and C(6–10), respectively). The ferrocene substituents attached in adjacent positions are directed away from each other so as to avoid spatial contacts and to minimize their steric influence on the ferrocene scaffold (cf. the torsion angle C11—C1—C2—P = 0.6 (4)°).

In the solid state, the individual molecules are involved in intra- and intermolecular C—H···O contacts (Table 1).

Related literature top

The title compound was prepared according to Breit & Breuninger (2005a). For a related structure, see: Lamač et al. (2009). For selected references concerning the use of enantiopure 2-(diphenylphosphino)ferrocene-1-carboxylic acids, see: Longmire et al. (2000, 2002); You et al. (2000, 2001); Štěpnička (2002); Breit & Breuninger (2004, 2005b,c); Lamač et al. (2007); Bianchini et al. (2008).

Experimental top

The title compound was prepared by esterification of racemic 2-(diphenylphosphino)ferrocene-1-carboxylic acid with glucose diacetonide (i.e., 1,2:5,6-di-O-isopropylidene-α-D-3-glucofuranose) followed by chromatographic separation of the resulting mixture of diastereoisomers (Breit & Breuninger, 2005a). X-ray quality crystals were grown by crystallization from diethyl ether-pentane at -18 °C.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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: PLATON (Spek, 2009).

Figures top

Fig. 1. A view of the molecular structure showing the atom numbering scheme and displacement ellipsoids for the non-H atoms at the 30% probability level.

1,2:5,6-Di-O-isopropylidene-α-D-3-glucofuranosyl (R_p)-2-(diphenylphosphino)ferrocene-1-carboxylate top

Crystal data top

[Fe(C₅H₅)(C₃₀H₃₂O₇P)]	F(000) = 1376
M_r = 656.47	D_x = 1.353 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4167 reflections
a = 10.3488 (1) Å	θ = 1.0–27.5°
b = 11.5379 (1) Å	µ = 0.57 mm⁻¹
c = 26.9830 (3) Å	T = 150 K
V = 3221.86 (6) Å³	Prism, orange
Z = 4	0.30 × 0.20 × 0.18 mm

Data collection top

Nonius KappaCCD diffractometer	6632 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.053
Horizontally mounted graphite crystal monochromator	θ_max = 27.5°, θ_min = 1.5°
Detector resolution: 9.091 pixels mm^-1	h = −13→13
ω and π scans to fill the Ewald sphere	k = −14→14
68616 measured reflections	l = −34→34
7369 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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0602P)² + 2.0459P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
7369 reflections	Δρ_max = 2.00 e Å⁻³
401 parameters	Δρ_min = −0.41 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 3230 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.012 (16)

Crystal data top

[Fe(C₅H₅)(C₃₀H₃₂O₇P)]	V = 3221.86 (6) Å³
M_r = 656.47	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.3488 (1) Å	µ = 0.57 mm⁻¹
b = 11.5379 (1) Å	T = 150 K
c = 26.9830 (3) Å	0.30 × 0.20 × 0.18 mm

Data collection top

Nonius KappaCCD diffractometer	6632 reflections with I > 2σ(I)
68616 measured reflections	R_int = 0.053
7369 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.112	Δρ_max = 2.00 e Å⁻³
S = 1.07	Δρ_min = −0.41 e Å⁻³
7369 reflections	Absolute structure: Flack (1983), 3230 Friedel pairs
401 parameters	Absolute structure parameter: −0.012 (16)
0 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Fe	0.75646 (3)	0.73651 (3)	0.085623 (12)	0.02205 (9)
P	0.67684 (7)	0.93927 (6)	0.17071 (3)	0.02765 (15)
O1	0.5336 (2)	0.9165 (2)	0.00514 (7)	0.0406 (5)
O2	0.48826 (16)	0.95039 (16)	0.08521 (7)	0.0250 (4)
C1	0.7010 (3)	0.8961 (2)	0.06389 (10)	0.0221 (5)
C2	0.7578 (3)	0.9010 (2)	0.11293 (9)	0.0224 (5)
C3	0.8872 (3)	0.8588 (2)	0.10792 (11)	0.0262 (6)
H3	0.9468	0.8517	0.1336	0.031*
C4	0.9102 (3)	0.8294 (2)	0.05762 (10)	0.0260 (6)
H4	0.9869	0.8000	0.0448	0.031*
C5	0.7963 (3)	0.8527 (2)	0.03036 (11)	0.0264 (6)
H5	0.7854	0.8416	−0.0035	0.032*
C6	0.5950 (3)	0.6355 (2)	0.09204 (12)	0.0332 (6)
H6	0.5102	0.6600	0.0873	0.040*
C7	0.6644 (3)	0.6387 (2)	0.13739 (11)	0.0353 (7)
H7	0.6327	0.6648	0.1676	0.042*
C8	0.7908 (3)	0.5949 (3)	0.12855 (12)	0.0364 (7)
H8	0.8566	0.5878	0.1518	0.044*
C9	0.7981 (3)	0.5639 (2)	0.07764 (12)	0.0325 (6)
H9	0.8698	0.5327	0.0617	0.039*
C10	0.6769 (3)	0.5888 (2)	0.05542 (12)	0.0337 (6)
H10	0.6552	0.5764	0.0224	0.040*
C11	0.5682 (3)	0.9205 (2)	0.04768 (10)	0.0242 (5)
C12	0.6543 (3)	1.0958 (2)	0.16384 (10)	0.0286 (6)
C13	0.5657 (3)	1.1494 (3)	0.19509 (13)	0.0374 (7)
H13	0.5208	1.1057	0.2184	0.045*
C14	0.5441 (4)	1.2664 (3)	0.19166 (16)	0.0527 (9)
H14	0.4854	1.3013	0.2131	0.063*
C15	0.6065 (4)	1.3323 (3)	0.15764 (19)	0.0614 (12)
H15	0.5906	1.4115	0.1557	0.074*
C16	0.6950 (4)	1.2801 (3)	0.12553 (17)	0.0568 (10)
H16	0.7378	1.3245	0.1019	0.068*
C17	0.7188 (3)	1.1630 (3)	0.12882 (13)	0.0428 (8)
H17	0.7783	1.1286	0.1076	0.051*
C18	0.8108 (3)	0.9280 (2)	0.21501 (10)	0.0312 (6)
C19	0.9024 (3)	1.0140 (3)	0.22259 (11)	0.0352 (7)
H19	0.9013	1.0804	0.2030	0.042*
C20	0.9958 (3)	1.0016 (3)	0.25926 (12)	0.0421 (8)
H20	1.0563	1.0600	0.2643	0.050*
C21	0.9992 (3)	0.9027 (3)	0.28826 (12)	0.0427 (8)
H21	1.0623	0.8945	0.3125	0.051*
C22	0.9091 (4)	0.8164 (3)	0.28114 (12)	0.0429 (8)
H22	0.9115	0.7498	0.3005	0.051*
C23	0.8147 (3)	0.8290 (3)	0.24498 (11)	0.0372 (7)
H23	0.7534	0.7709	0.2406	0.045*
O31	0.2736 (2)	1.05237 (18)	0.14377 (7)	0.0370 (5)
O32	0.1519 (3)	1.1833 (2)	0.09835 (9)	0.0525 (7)
O33	0.2334 (2)	1.11358 (17)	0.02688 (7)	0.0357 (5)
O34	0.3015 (2)	0.74486 (18)	0.11693 (7)	0.0348 (5)
O35	0.14038 (19)	0.7207 (2)	0.17217 (8)	0.0374 (5)
C31	0.2789 (3)	1.1452 (3)	0.11065 (12)	0.0373 (7)
H31	0.3312	1.2088	0.1240	0.045*
C32	0.3346 (3)	1.1002 (2)	0.06165 (11)	0.0293 (6)
H32	0.4140	1.1403	0.0518	0.035*
C33	0.3552 (2)	0.9699 (2)	0.07100 (10)	0.0260 (6)
H33	0.3307	0.9231	0.0422	0.031*
C34	0.2681 (3)	0.9470 (3)	0.11491 (10)	0.0299 (6)
H34	0.1795	0.9356	0.1030	0.036*
C35	0.3053 (3)	0.8459 (3)	0.14770 (11)	0.0319 (6)
H35	0.3920	0.8571	0.1615	0.038*
C36	0.2076 (3)	0.8218 (3)	0.18907 (12)	0.0401 (7)
H36A	0.2510	0.8071	0.2203	0.048*
H36B	0.1487	0.8865	0.1932	0.048*
C37	0.1424 (3)	1.1947 (3)	0.04633 (12)	0.0348 (7)
C38	0.1743 (4)	1.3153 (3)	0.02899 (17)	0.0534 (9)
H38A	0.1140	1.3693	0.0431	0.080*
H38B	0.1692	1.3185	−0.0065	0.080*
H38C	0.2603	1.3351	0.0394	0.080*
C39	0.0093 (3)	1.1574 (4)	0.02956 (19)	0.0577 (10)
H39A	−0.0124	1.0848	0.0448	0.087*
H39B	0.0087	1.1486	−0.0058	0.087*
H39C	−0.0529	1.2150	0.0390	0.087*
C40	0.2314 (3)	0.6572 (3)	0.14332 (10)	0.0319 (6)
C41	0.3214 (3)	0.5871 (3)	0.17559 (12)	0.0430 (8)
H41A	0.3676	0.6381	0.1974	0.065*
H41B	0.3817	0.5460	0.1551	0.065*
H41C	0.2722	0.5328	0.1948	0.065*
C42	0.1585 (4)	0.5848 (3)	0.10663 (13)	0.0467 (8)
H42A	0.1134	0.5241	0.1237	0.070*
H42B	0.2180	0.5513	0.0834	0.070*
H42C	0.0975	0.6325	0.0893	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe	0.02177 (17)	0.02121 (16)	0.02317 (17)	0.00037 (15)	0.00262 (15)	−0.00003 (13)
P	0.0337 (4)	0.0239 (3)	0.0253 (3)	0.0028 (3)	0.0028 (3)	−0.0012 (3)
O1	0.0324 (11)	0.0661 (16)	0.0233 (10)	0.0081 (11)	−0.0023 (8)	−0.0013 (10)
O2	0.0197 (8)	0.0311 (9)	0.0241 (9)	0.0034 (7)	−0.0025 (7)	−0.0028 (8)
C1	0.0224 (12)	0.0207 (11)	0.0232 (12)	0.0016 (9)	0.0020 (10)	−0.0002 (10)
C2	0.0220 (12)	0.0191 (10)	0.0261 (11)	−0.0010 (11)	0.0001 (12)	0.0003 (9)
C3	0.0209 (13)	0.0259 (13)	0.0319 (14)	−0.0008 (10)	−0.0036 (11)	−0.0005 (11)
C4	0.0198 (12)	0.0262 (14)	0.0320 (14)	−0.0001 (10)	0.0077 (11)	0.0037 (11)
C5	0.0253 (13)	0.0272 (13)	0.0267 (13)	−0.0005 (10)	0.0028 (10)	0.0063 (11)
C6	0.0252 (13)	0.0252 (13)	0.0491 (18)	−0.0047 (10)	0.0067 (13)	−0.0001 (13)
C7	0.0468 (18)	0.0262 (14)	0.0330 (15)	−0.0044 (13)	0.0190 (14)	0.0017 (12)
C8	0.0441 (18)	0.0248 (13)	0.0401 (17)	−0.0016 (12)	−0.0016 (13)	0.0099 (12)
C9	0.0349 (14)	0.0191 (12)	0.0436 (17)	0.0031 (10)	0.0117 (12)	−0.0012 (12)
C10	0.0367 (16)	0.0275 (14)	0.0369 (16)	−0.0055 (12)	0.0041 (13)	−0.0066 (12)
C11	0.0246 (13)	0.0237 (13)	0.0243 (13)	0.0003 (10)	0.0006 (10)	0.0012 (10)
C12	0.0291 (14)	0.0256 (12)	0.0310 (14)	0.0000 (11)	−0.0072 (11)	−0.0032 (11)
C13	0.0324 (16)	0.0362 (16)	0.0437 (18)	0.0045 (13)	−0.0024 (13)	−0.0103 (14)
C14	0.0422 (18)	0.0366 (18)	0.079 (3)	0.0080 (16)	−0.0027 (17)	−0.0191 (19)
C15	0.056 (2)	0.0242 (16)	0.104 (4)	0.0048 (16)	−0.023 (2)	−0.0059 (19)
C16	0.068 (2)	0.0303 (17)	0.072 (3)	−0.0042 (17)	0.002 (2)	0.0071 (17)
C17	0.055 (2)	0.0261 (14)	0.0474 (19)	−0.0005 (14)	0.0070 (15)	−0.0008 (13)
C18	0.0401 (15)	0.0304 (14)	0.0231 (13)	0.0070 (12)	0.0024 (11)	−0.0044 (11)
C19	0.0413 (17)	0.0359 (15)	0.0284 (15)	0.0032 (13)	−0.0054 (13)	−0.0015 (12)
C20	0.0406 (17)	0.048 (2)	0.0373 (18)	0.0037 (15)	−0.0029 (15)	−0.0089 (15)
C21	0.0441 (19)	0.055 (2)	0.0285 (15)	0.0132 (16)	−0.0079 (14)	−0.0078 (14)
C22	0.058 (2)	0.0410 (18)	0.0298 (16)	0.0161 (16)	−0.0012 (15)	0.0017 (13)
C23	0.0480 (18)	0.0322 (15)	0.0315 (15)	0.0067 (14)	−0.0010 (14)	−0.0008 (12)
O31	0.0423 (12)	0.0388 (11)	0.0300 (10)	0.0069 (10)	0.0007 (9)	−0.0086 (9)
O32	0.0508 (14)	0.0652 (17)	0.0415 (13)	0.0302 (13)	0.0041 (11)	−0.0036 (11)
O33	0.0382 (12)	0.0353 (10)	0.0337 (10)	0.0132 (10)	−0.0098 (10)	−0.0054 (8)
O34	0.0381 (10)	0.0327 (11)	0.0335 (10)	0.0007 (9)	0.0119 (8)	0.0062 (9)
O35	0.0267 (10)	0.0502 (13)	0.0352 (11)	0.0015 (9)	0.0087 (8)	0.0063 (10)
C31	0.0432 (18)	0.0335 (15)	0.0353 (15)	0.0086 (13)	−0.0087 (13)	−0.0072 (12)
C32	0.0261 (14)	0.0269 (13)	0.0349 (14)	0.0052 (11)	−0.0029 (12)	−0.0012 (11)
C33	0.0212 (12)	0.0279 (13)	0.0289 (13)	0.0031 (10)	−0.0031 (10)	−0.0016 (10)
C34	0.0240 (13)	0.0350 (14)	0.0308 (13)	−0.0001 (12)	−0.0013 (11)	−0.0029 (11)
C35	0.0249 (13)	0.0397 (16)	0.0310 (15)	−0.0010 (12)	0.0031 (11)	0.0030 (12)
C36	0.0383 (17)	0.0512 (19)	0.0307 (15)	−0.0003 (14)	0.0081 (12)	−0.0011 (14)
C37	0.0296 (15)	0.0320 (15)	0.0427 (17)	0.0098 (12)	−0.0025 (13)	−0.0013 (13)
C38	0.048 (2)	0.0327 (16)	0.079 (3)	0.0075 (16)	0.007 (2)	0.0024 (17)
C39	0.0371 (19)	0.050 (2)	0.086 (3)	0.0038 (16)	−0.0101 (19)	0.003 (2)
C40	0.0290 (15)	0.0387 (14)	0.0280 (13)	−0.0009 (12)	0.0043 (12)	0.0079 (11)
C41	0.0363 (16)	0.0530 (19)	0.0398 (17)	0.0037 (15)	0.0064 (14)	0.0161 (15)
C42	0.051 (2)	0.048 (2)	0.0415 (18)	−0.0077 (17)	−0.0051 (16)	0.0030 (15)

Geometric parameters (Å, º) top

Fe—C1	2.016 (3)	C19—C20	1.391 (4)
Fe—C7	2.033 (3)	C19—H19	0.9300
Fe—C8	2.034 (3)	C20—C21	1.383 (5)
Fe—C2	2.035 (2)	C20—H20	0.9300
Fe—C6	2.045 (3)	C21—C22	1.378 (5)
Fe—C3	2.045 (3)	C21—H21	0.9300
Fe—C5	2.047 (3)	C22—C23	1.388 (5)
Fe—C9	2.050 (3)	C22—H22	0.9300
Fe—C10	2.061 (3)	C23—H23	0.9300
Fe—C4	2.062 (3)	O31—C31	1.396 (4)
P—C2	1.824 (3)	O31—C34	1.445 (3)
P—C12	1.831 (3)	O32—C37	1.413 (4)
P—C18	1.835 (3)	O32—C31	1.426 (4)
O1—C11	1.203 (3)	O33—C32	1.415 (3)
O2—C11	1.352 (3)	O33—C37	1.428 (4)
O2—C33	1.447 (3)	O34—C35	1.432 (4)
C1—C5	1.429 (4)	O34—C40	1.434 (3)
C1—C2	1.449 (4)	O35—C40	1.425 (4)
C1—C11	1.469 (4)	O35—C36	1.432 (4)
C2—C3	1.432 (4)	C31—C32	1.533 (4)
C3—C4	1.419 (4)	C31—H31	0.9800
C3—H3	0.9300	C32—C33	1.540 (4)
C4—C5	1.415 (4)	C32—H32	0.9800
C4—H4	0.9300	C33—C34	1.512 (4)
C5—H5	0.9300	C33—H33	0.9800
C6—C10	1.409 (4)	C34—C35	1.514 (4)
C6—C7	1.419 (5)	C34—H34	0.9800
C6—H6	0.9300	C35—C36	1.531 (4)
C7—C8	1.423 (5)	C35—H35	0.9800
C7—H7	0.9300	C36—H36A	0.9700
C8—C9	1.422 (5)	C36—H36B	0.9700
C8—H8	0.9300	C37—C38	1.505 (5)
C9—C10	1.420 (4)	C37—C39	1.512 (5)
C9—H9	0.9300	C38—H38A	0.9600
C10—H10	0.9300	C38—H38B	0.9600
C12—C13	1.391 (4)	C38—H38C	0.9600
C12—C17	1.393 (4)	C39—H39A	0.9600
C13—C14	1.372 (5)	C39—H39B	0.9600
C13—H13	0.9300	C39—H39C	0.9600
C14—C15	1.356 (6)	C40—C42	1.499 (4)
C14—H14	0.9300	C40—C41	1.510 (4)
C15—C16	1.397 (6)	C41—H41A	0.9600
C15—H15	0.9300	C41—H41B	0.9600
C16—C17	1.375 (5)	C41—H41C	0.9600
C16—H16	0.9300	C42—H42A	0.9600
C17—H17	0.9300	C42—H42B	0.9600
C18—C19	1.387 (4)	C42—H42C	0.9600
C18—C23	1.401 (4)

C1—Fe—C7	124.99 (12)	C13—C12—P	117.5 (2)
C1—Fe—C8	161.64 (12)	C17—C12—P	123.8 (2)
C7—Fe—C8	40.94 (13)	C14—C13—C12	120.3 (3)
C1—Fe—C2	41.92 (10)	C14—C13—H13	119.9
C7—Fe—C2	105.79 (11)	C12—C13—H13	119.9
C8—Fe—C2	122.79 (12)	C15—C14—C13	121.3 (4)
C1—Fe—C6	108.19 (11)	C15—C14—H14	119.3
C7—Fe—C6	40.73 (14)	C13—C14—H14	119.3
C8—Fe—C6	68.69 (13)	C14—C15—C16	119.4 (3)
C2—Fe—C6	120.40 (11)	C14—C15—H15	120.3
C1—Fe—C3	69.16 (11)	C16—C15—H15	120.3
C7—Fe—C3	119.41 (12)	C17—C16—C15	120.0 (4)
C8—Fe—C3	105.73 (13)	C17—C16—H16	120.0
C2—Fe—C3	41.07 (11)	C15—C16—H16	120.0
C6—Fe—C3	155.36 (12)	C16—C17—C12	120.3 (3)
C1—Fe—C5	41.19 (10)	C16—C17—H17	119.9
C7—Fe—C5	163.43 (12)	C12—C17—H17	119.8
C8—Fe—C5	154.91 (12)	C19—C18—C23	118.6 (3)
C2—Fe—C5	69.64 (10)	C19—C18—P	124.2 (2)
C6—Fe—C5	126.84 (12)	C23—C18—P	117.1 (2)
C3—Fe—C5	68.24 (11)	C18—C19—C20	120.4 (3)
C1—Fe—C9	156.50 (12)	C18—C19—H19	119.8
C7—Fe—C9	68.36 (12)	C20—C19—H19	119.8
C8—Fe—C9	40.74 (13)	C21—C20—C19	120.4 (3)
C2—Fe—C9	160.49 (12)	C21—C20—H20	119.8
C6—Fe—C9	68.10 (11)	C19—C20—H20	119.8
C3—Fe—C9	124.19 (12)	C22—C21—C20	120.0 (3)
C5—Fe—C9	121.16 (12)	C22—C21—H21	120.0
C1—Fe—C10	121.76 (12)	C20—C21—H21	120.0
C7—Fe—C10	67.98 (12)	C21—C22—C23	119.9 (3)
C8—Fe—C10	68.32 (14)	C21—C22—H22	120.0
C2—Fe—C10	156.46 (12)	C23—C22—H22	120.0
C6—Fe—C10	40.14 (12)	C22—C23—C18	120.7 (3)
C3—Fe—C10	162.01 (12)	C22—C23—H23	119.6
C5—Fe—C10	109.51 (12)	C18—C23—H23	119.6
C9—Fe—C10	40.43 (12)	C31—O31—C34	107.6 (2)
C1—Fe—C4	68.81 (11)	C37—O32—C31	108.9 (2)
C7—Fe—C4	154.44 (13)	C32—O33—C37	108.4 (2)
C8—Fe—C4	119.45 (12)	C35—O34—C40	107.5 (2)
C2—Fe—C4	69.07 (11)	C40—O35—C36	105.8 (2)
C6—Fe—C4	163.34 (12)	O31—C31—O32	110.4 (3)
C3—Fe—C4	40.41 (11)	O31—C31—C32	107.9 (2)
C5—Fe—C4	40.29 (11)	O32—C31—C32	104.5 (2)
C9—Fe—C4	107.72 (11)	O31—C31—H31	111.2
C10—Fe—C4	126.40 (12)	O32—C31—H31	111.2
C2—P—C12	102.19 (12)	C32—C31—H31	111.2
C2—P—C18	101.10 (13)	O33—C32—C31	104.9 (2)
C12—P—C18	103.40 (13)	O33—C32—C33	108.5 (2)
C11—O2—C33	115.1 (2)	C31—C32—C33	103.9 (2)
C5—C1—C2	108.1 (2)	O33—C32—H32	112.9
C5—C1—C11	121.6 (2)	C31—C32—H32	112.9
C2—C1—C11	130.1 (2)	C33—C32—H32	112.9
C5—C1—Fe	70.57 (15)	O2—C33—C34	109.4 (2)
C2—C1—Fe	69.77 (14)	O2—C33—C32	109.1 (2)
C11—C1—Fe	121.91 (19)	C34—C33—C32	102.5 (2)
C3—C2—C1	106.3 (2)	O2—C33—H33	111.8
C3—C2—P	126.4 (2)	C34—C33—H33	111.8
C1—C2—P	127.1 (2)	C32—C33—H33	111.8
C3—C2—Fe	69.83 (14)	O31—C34—C33	104.6 (2)
C1—C2—Fe	68.31 (14)	O31—C34—C35	108.9 (2)
P—C2—Fe	122.15 (13)	C33—C34—C35	116.2 (2)
C4—C3—C2	109.2 (2)	O31—C34—H34	109.0
C4—C3—Fe	70.44 (16)	C33—C34—H34	109.0
C2—C3—Fe	69.10 (14)	C35—C34—H34	109.0
C4—C3—H3	125.4	O34—C35—C34	106.3 (2)
C2—C3—H3	125.4	O34—C35—C36	104.9 (2)
Fe—C3—H3	126.6	C34—C35—C36	113.4 (3)
C5—C4—C3	108.2 (2)	O34—C35—H35	110.6
C5—C4—Fe	69.26 (15)	C34—C35—H35	110.6
C3—C4—Fe	69.15 (16)	C36—C35—H35	110.6
C5—C4—H4	125.9	O35—C36—C35	103.7 (2)
C3—C4—H4	125.9	O35—C36—H36A	111.0
Fe—C4—H4	127.3	C35—C36—H36A	111.0
C4—C5—C1	108.2 (2)	O35—C36—H36B	111.0
C4—C5—Fe	70.45 (15)	C35—C36—H36B	111.0
C1—C5—Fe	68.24 (15)	H36A—C36—H36B	109.0
C4—C5—H5	125.9	O32—C37—O33	105.0 (2)
C1—C5—H5	125.9	O32—C37—C38	112.3 (3)
Fe—C5—H5	127.0	O33—C37—C38	110.3 (3)
C10—C6—C7	108.1 (3)	O32—C37—C39	109.5 (3)
C10—C6—Fe	70.55 (17)	O33—C37—C39	107.7 (3)
C7—C6—Fe	69.20 (16)	C38—C37—C39	111.8 (3)
C10—C6—H6	126.0	C37—C38—H38A	109.5
C7—C6—H6	126.0	C37—C38—H38B	109.5
Fe—C6—H6	125.9	H38A—C38—H38B	109.5
C6—C7—C8	108.2 (3)	C37—C38—H38C	109.5
C6—C7—Fe	70.07 (16)	H38A—C38—H38C	109.5
C8—C7—Fe	69.57 (17)	H38B—C38—H38C	109.5
C6—C7—H7	125.9	C37—C39—H39A	109.5
C8—C7—H7	125.9	C37—C39—H39B	109.5
Fe—C7—H7	126.0	H39A—C39—H39B	109.5
C9—C8—C7	107.5 (3)	C37—C39—H39C	109.5
C9—C8—Fe	70.20 (17)	H39A—C39—H39C	109.5
C7—C8—Fe	69.49 (17)	H39B—C39—H39C	109.5
C9—C8—H8	126.2	O35—C40—O34	104.1 (2)
C7—C8—H8	126.2	O35—C40—C42	108.4 (3)
Fe—C8—H8	125.6	O34—C40—C42	108.6 (2)
C10—C9—C8	108.0 (3)	O35—C40—C41	111.6 (2)
C10—C9—Fe	70.23 (16)	O34—C40—C41	110.6 (2)
C8—C9—Fe	69.06 (16)	C42—C40—C41	113.1 (3)
C10—C9—H9	126.0	C40—C41—H41A	109.5
C8—C9—H9	126.0	C40—C41—H41B	109.5
Fe—C9—H9	126.3	H41A—C41—H41B	109.5
C6—C10—C9	108.2 (3)	C40—C41—H41C	109.5
C6—C10—Fe	69.31 (16)	H41A—C41—H41C	109.5
C9—C10—Fe	69.35 (17)	H41B—C41—H41C	109.5
C6—C10—H10	125.9	C40—C42—H42A	109.5
C9—C10—H10	125.9	C40—C42—H42B	109.5
Fe—C10—H10	127.0	H42A—C42—H42B	109.5
O1—C11—O2	122.8 (2)	C40—C42—H42C	109.5
O1—C11—C1	123.7 (3)	H42A—C42—H42C	109.5
O2—C11—C1	113.5 (2)	H42B—C42—H42C	109.5
C13—C12—C17	118.7 (3)

C5—C1—C2—C3	−0.6 (3)	C21—C22—C23—C18	0.8 (5)
C11—C1—C2—C3	175.0 (3)	C19—C18—C23—C22	−0.7 (4)
C5—C1—C2—P	−175.07 (19)	P—C18—C23—C22	−176.8 (2)
C11—C1—C2—P	0.6 (4)	C34—O31—C31—O32	89.5 (3)
C12—P—C2—C3	114.0 (2)	C34—O31—C31—C32	−24.1 (3)
C18—P—C2—C3	7.5 (3)	C37—O32—C31—O31	−131.8 (3)
C12—P—C2—C1	−72.6 (2)	C37—O32—C31—C32	−16.0 (3)
C18—P—C2—C1	−179.1 (2)	C37—O33—C32—C31	18.8 (3)
C1—C2—C3—C4	0.3 (3)	C37—O33—C32—C33	129.4 (2)
P—C2—C3—C4	174.88 (19)	O31—C31—C32—O33	115.8 (3)
C2—C3—C4—C5	0.0 (3)	O32—C31—C32—O33	−1.8 (3)
C3—C4—C5—C1	−0.4 (3)	O31—C31—C32—C33	1.9 (3)
C2—C1—C5—C4	0.6 (3)	O32—C31—C32—C33	−115.7 (3)
C11—C1—C5—C4	−175.5 (2)	C11—O2—C33—C34	153.8 (2)
C10—C6—C7—C8	0.7 (3)	C11—O2—C33—C32	−94.9 (3)
C6—C7—C8—C9	−0.5 (3)	O33—C32—C33—O2	152.3 (2)
C7—C8—C9—C10	0.1 (3)	C31—C32—C33—O2	−96.4 (3)
C7—C6—C10—C9	−0.7 (3)	O33—C32—C33—C34	−91.8 (3)
C8—C9—C10—C6	0.4 (3)	C31—C32—C33—C34	19.5 (3)
C33—O2—C11—O1	3.9 (4)	C31—O31—C34—C33	37.1 (3)
C33—O2—C11—C1	−177.2 (2)	C31—O31—C34—C35	161.9 (2)
C5—C1—C11—O1	−7.2 (4)	O2—C33—C34—O31	81.6 (3)
C2—C1—C11—O1	177.7 (3)	C32—C33—C34—O31	−34.1 (3)
C5—C1—C11—O2	174.0 (2)	O2—C33—C34—C35	−38.4 (3)
C2—C1—C11—O2	−1.1 (4)	C32—C33—C34—C35	−154.1 (2)
C2—P—C12—C13	163.4 (2)	C40—O34—C35—C34	−132.7 (2)
C18—P—C12—C13	−91.8 (2)	C40—O34—C35—C36	−12.2 (3)
C2—P—C12—C17	−15.4 (3)	O31—C34—C35—O34	−178.5 (2)
C18—P—C12—C17	89.3 (3)	C33—C34—C35—O34	−60.8 (3)
C17—C12—C13—C14	−0.8 (5)	O31—C34—C35—C36	66.7 (3)
P—C12—C13—C14	−179.8 (3)	C33—C34—C35—C36	−175.6 (3)
C12—C13—C14—C15	0.9 (5)	C40—O35—C36—C35	30.5 (3)
C13—C14—C15—C16	−0.2 (6)	O34—C35—C36—O35	−11.1 (3)
C14—C15—C16—C17	−0.5 (6)	C34—C35—C36—O35	104.6 (3)
C15—C16—C17—C12	0.5 (6)	C31—O32—C37—O33	27.8 (3)
C13—C12—C17—C16	0.2 (5)	C31—O32—C37—C38	−92.1 (3)
P—C12—C17—C16	179.0 (3)	C31—O32—C37—C39	143.1 (3)
C2—P—C18—C19	81.3 (3)	C32—O33—C37—O32	−29.0 (3)
C12—P—C18—C19	−24.2 (3)	C32—O33—C37—C38	92.2 (3)
C2—P—C18—C23	−102.9 (2)	C32—O33—C37—C39	−145.6 (3)
C12—P—C18—C23	151.6 (2)	C36—O35—C40—O34	−38.8 (3)
C23—C18—C19—C20	0.0 (4)	C36—O35—C40—C42	−154.2 (3)
P—C18—C19—C20	175.7 (2)	C36—O35—C40—C41	80.5 (3)
C18—C19—C20—C21	0.7 (5)	C35—O34—C40—O35	31.3 (3)
C19—C20—C21—C22	−0.5 (5)	C35—O34—C40—C42	146.6 (3)
C20—C21—C22—C23	−0.2 (5)	C35—O34—C40—C41	−88.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O34	0.93	2.50	3.357 (4)	153
C9—H9···O1ⁱ	0.93	2.54	3.314 (4)	140

Symmetry code: (i) x+1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₃₀H₃₂O₇P)]
M_r	656.47
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	150
a, b, c (Å)	10.3488 (1), 11.5379 (1), 26.9830 (3)
V (Å³)	3221.86 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.57
Crystal size (mm)	0.30 × 0.20 × 0.18

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	68616, 7369, 6632
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.112, 1.07
No. of reflections	7369
No. of parameters	401
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.00, −0.41
Absolute structure	Flack (1983), 3230 Friedel pairs
Absolute structure parameter	−0.012 (16)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O34	0.93	2.50	3.357 (4)	153
C9—H9···O1ⁱ	0.93	2.54	3.314 (4)	140

Symmetry code: (i) x+1/2, −y+3/2, −z.

Acknowledgements

This work is a part of the long-term research projects supported by the Ministry of Education, Youth and Sports of the Czech Republic (project Nos. LC06070 and MSM0021620857).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 65| Part 10| October 2009| Pages m1252-m1253

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1,2:5,6-Di-O-iso­propyl­­idene-α-D-3-gluco­furanosyl (Rp)-2-(di­phenyl­phosphino)ferrocene-1-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

1,2:5,6-Di-O-isopropylidene-α-D-3-glucofuranosyl (R_p)-2-(diphenylphosphino)ferrocene-1-carboxylate