1,2:5,6-Di-O-isopropyl-idene-α-d-3-glucofuranosyl (R(p))-2-(diphenyl-phosphino)ferrocene-1-carboxyl-ate.

The title compound, [Fe(C(5)H(5))(C(30)H(32)O(7)P)], which is an inter-mediate in the synthesis of (R(p))-2-(diphenyl-phos-phino)ferrocene-1-carboxylic acid, crystallizes in the common chiral space group P2(1)2(1)2(1). In general, the mol-ecular geometry is very similar to that of the corresponding 2,1'-bis-(diphenyl-phosphino) congener. The ferrocene unit assumes a regular geometry with the proximal bulky substituents efficiently avoiding mutual spatial contacts. In the crystal, the mol-ecules participate in weak intra- and inter-molecular C-H⋯O inter-actions.

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 = 656.47

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.112

S = 1.07

7369 reflections

401 parameters

H-atom parameters constrained

Δρmax = 2.00 e Å−3

Δρmin = −0.41 e Å−3

Absolute structure: Flack (1983 ▶), 3230 Friedel pairs

Flack parameter: −0.012 (16)

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Fe(C5H5)(C30H32O7P)]	F(000) = 1376
Mr = 656.47	Dx = 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 = 0.56 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

Nonius KappaCCD diffractometer	6632 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
horizontally mounted graphite crystal	θmax = 27.5°, θmin = 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 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(Fo2) + (0.0602P)2 + 2.0459P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
7369 reflections	Δρmax = 2.00 e Å−3
401 parameters	Δρmin = −0.41 e Å−3
0 restraints	Absolute structure: Flack (1983), 3230 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.012 (16)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .