(E)-1-Ferrocenyl-3-[2-(2-hy-droxy-eth-oxy)phen-yl]prop-2-en-1-one.

In the title compound, [Fe(C5H5)(C16H15O3)], the cyclo-penta-dienyl rings are in an eclipsed conformation and the benzene ring makes dihedral angles of 10.84 (9) and 12.35 (9)°, respectively, with the substituted and unsubstituted cyclo-penta-dienyl rings. In the crystal, mol-ecules form inversion dimers through pairs of O-H⋯O hydrogen bonds. Weak C-H⋯O hydrogen bonds are observed between the dimers.

Related literature

For the biological activity of ferrocenyl derivatives, see: Jaouen et al. (2004 ▶); Fouda et al. (2007 ▶); Biot et al. (2004 ▶); Edwards et al. (1975 ▶). For a related structure, see: Zora et al. (2006 ▶).

Experimental

Crystal data

[Fe(C5H5)(C16H15O3)]

M = 376.22

Monoclinic,

a = 12.5649 (10) Å

b = 19.0531 (14) Å

c = 7.4930 (6) Å

β = 103.932 (3)°

V = 1741.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.88 mm−1

T = 298 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

16289 measured reflections

4310 independent reflections

3510 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.096

S = 1.06

4310 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813003395/is5242sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003395/is5242Isup2.hkl

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

[Fe(C5H5)(C16H15O3)]	F(000) = 784
Mr = 376.22	Monoclinic
Monoclinic, P21/c	Dx = 1.435 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.5649 (10) Å	Cell parameters from 4310 reflections
b = 19.0531 (14) Å	θ = 1.7–28.3°
c = 7.4930 (6) Å	µ = 0.88 mm−1
β = 103.932 (3)°	T = 298 K
V = 1741.1 (2) Å3	Block, colourless
Z = 4	0.20 × 0.20 × 0.20 mm

Bruker SMART APEXII area-detector diffractometer	3510 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
Graphite monochromator	θmax = 28.3°, θmin = 1.7°
ω and φ scans	h = −13→16
16289 measured reflections	k = −24→25
4310 independent reflections	l = −9→9

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.044P)2 + 0.321P] where P = (Fo2 + 2Fc2)/3
4310 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.5017 (2)	0.19106 (15)	0.1792 (4)	0.0844 (8)
H1A	0.4927	0.2107	0.0571	0.101*
H1B	0.5491	0.2224	0.2651	0.101*
C2	0.3913 (2)	0.18912 (13)	0.2245 (3)	0.0687 (6)
H2A	0.3620	0.2362	0.2247	0.082*
H2B	0.3402	0.1612	0.1345	0.082*
C3	0.32089 (15)	0.14956 (9)	0.4781 (2)	0.0448 (4)
C4	0.21972 (18)	0.18139 (11)	0.4123 (3)	0.0601 (5)
H4	0.2076	0.2092	0.3075	0.072*
C5	0.13711 (18)	0.17179 (13)	0.5021 (4)	0.0689 (6)
H5	0.0694	0.1931	0.4568	0.083*
C6	0.15347 (17)	0.13110 (14)	0.6575 (3)	0.0665 (6)
H6	0.0977	0.1254	0.7185	0.080*
C7	0.25349 (16)	0.09891 (10)	0.7221 (3)	0.0526 (5)
H7	0.2642	0.0712	0.8271	0.063*
C8	0.33932 (14)	0.10650 (9)	0.6351 (2)	0.0399 (4)
C9	0.44013 (13)	0.06738 (9)	0.7103 (2)	0.0396 (4)
H9	0.4388	0.0402	0.8129	0.048*
C10	0.53325 (13)	0.06421 (9)	0.6567 (2)	0.0404 (4)
H10	0.5416	0.0911	0.5572	0.048*
C11	0.62388 (14)	0.01847 (9)	0.7532 (2)	0.0402 (4)
C12	0.72924 (13)	0.02332 (9)	0.7018 (2)	0.0420 (4)
C13	0.82896 (14)	−0.00662 (10)	0.8068 (3)	0.0494 (4)
H13	0.8358	−0.0356	0.9087	0.059*
C14	0.91522 (16)	0.01531 (12)	0.7295 (3)	0.0582 (5)
H14	0.9889	0.0038	0.7722	0.070*
C15	0.86994 (16)	0.05775 (14)	0.5762 (3)	0.0618 (6)
H15	0.9090	0.0785	0.4993	0.074*
C16	0.75584 (15)	0.06370 (12)	0.5579 (2)	0.0524 (5)
H16	0.7069	0.0892	0.4686	0.063*
C17	0.8640 (3)	0.13448 (14)	1.0708 (3)	0.0789 (8)
H17	0.8730	0.1060	1.1741	0.095*
C18	0.7635 (2)	0.16178 (13)	0.9658 (4)	0.0694 (7)
H18	0.6943	0.1543	0.9866	0.083*
C19	0.7877 (2)	0.20164 (12)	0.8261 (4)	0.0678 (6)
H19	0.7370	0.2260	0.7366	0.081*
C20	0.8997 (2)	0.19941 (12)	0.8411 (4)	0.0699 (6)
H20	0.9365	0.2218	0.7635	0.084*
C21	0.9477 (2)	0.15830 (14)	0.9908 (4)	0.0736 (7)
H21	1.0220	0.1482	1.0313	0.088*
O1	0.55410 (15)	0.12565 (11)	0.1848 (3)	0.0782 (5)
H1	0.5047	0.0927	0.1474	0.117*
O2	0.40793 (11)	0.15843 (7)	0.40196 (18)	0.0548 (3)
O3	0.61383 (11)	−0.02233 (8)	0.8744 (2)	0.0571 (4)
Fe1	0.836512 (18)	0.100494 (12)	0.80775 (3)	0.03666 (9)

	U11	U22	U33	U12	U13	U23
C1	0.103 (2)	0.0783 (18)	0.0778 (16)	−0.0097 (15)	0.0332 (15)	0.0336 (14)
C2	0.0914 (17)	0.0574 (13)	0.0560 (12)	0.0086 (12)	0.0153 (11)	0.0243 (10)
C3	0.0480 (10)	0.0372 (9)	0.0448 (9)	0.0023 (7)	0.0027 (7)	−0.0046 (7)
C4	0.0599 (13)	0.0495 (11)	0.0606 (12)	0.0114 (9)	−0.0060 (10)	0.0000 (9)
C5	0.0438 (11)	0.0668 (14)	0.0871 (17)	0.0170 (10)	−0.0018 (11)	−0.0118 (13)
C6	0.0416 (11)	0.0781 (16)	0.0801 (15)	0.0070 (10)	0.0148 (10)	−0.0087 (13)
C7	0.0430 (10)	0.0591 (12)	0.0563 (11)	0.0033 (8)	0.0129 (9)	−0.0027 (9)
C8	0.0376 (9)	0.0397 (9)	0.0401 (9)	0.0008 (7)	0.0049 (7)	−0.0048 (7)
C9	0.0403 (9)	0.0401 (9)	0.0369 (8)	0.0001 (7)	0.0062 (7)	0.0017 (7)
C10	0.0382 (9)	0.0427 (9)	0.0391 (8)	−0.0022 (7)	0.0069 (7)	0.0030 (7)
C11	0.0364 (8)	0.0406 (9)	0.0414 (8)	−0.0028 (7)	0.0050 (7)	−0.0017 (7)
C12	0.0357 (8)	0.0444 (9)	0.0446 (9)	−0.0029 (7)	0.0070 (7)	−0.0090 (7)
C13	0.0420 (10)	0.0387 (9)	0.0651 (12)	0.0055 (7)	0.0081 (9)	−0.0057 (8)
C14	0.0390 (10)	0.0648 (13)	0.0709 (13)	0.0059 (9)	0.0136 (9)	−0.0197 (11)
C15	0.0453 (11)	0.0962 (17)	0.0485 (11)	−0.0104 (11)	0.0202 (9)	−0.0186 (11)
C16	0.0413 (10)	0.0805 (14)	0.0345 (9)	−0.0070 (9)	0.0071 (7)	−0.0078 (9)
C17	0.136 (3)	0.0599 (14)	0.0382 (11)	−0.0018 (15)	0.0168 (13)	−0.0121 (10)
C18	0.0701 (15)	0.0620 (14)	0.0872 (16)	−0.0094 (11)	0.0408 (13)	−0.0304 (12)
C19	0.0680 (15)	0.0461 (12)	0.0873 (16)	0.0113 (10)	0.0148 (12)	0.0026 (11)
C20	0.0710 (15)	0.0470 (12)	0.0943 (17)	−0.0173 (11)	0.0252 (13)	−0.0041 (12)
C21	0.0580 (13)	0.0725 (16)	0.0782 (16)	−0.0002 (12)	−0.0072 (12)	−0.0310 (13)
O1	0.0659 (10)	0.0967 (13)	0.0755 (11)	−0.0164 (10)	0.0240 (9)	0.0026 (10)
O2	0.0587 (8)	0.0565 (8)	0.0475 (7)	0.0058 (6)	0.0097 (6)	0.0163 (6)
O3	0.0449 (7)	0.0590 (8)	0.0663 (8)	0.0020 (6)	0.0111 (6)	0.0228 (7)
Fe1	0.03431 (14)	0.03993 (15)	0.03509 (14)	−0.00033 (9)	0.00705 (10)	−0.00048 (9)

C1—O1	1.406 (3)	C13—C14	1.409 (3)
C1—C2	1.505 (4)	C13—Fe1	2.0429 (19)
C1—H1A	0.9700	C13—H13	0.9300
C1—H1B	0.9700	C14—C15	1.408 (3)
C2—O2	1.421 (2)	C14—Fe1	2.0579 (19)
C2—H2A	0.9700	C14—H14	0.9300
C2—H2B	0.9700	C15—C16	1.412 (3)
C3—O2	1.361 (2)	C15—Fe1	2.0496 (19)
C3—C4	1.387 (3)	C15—H15	0.9300
C3—C8	1.406 (3)	C16—Fe1	2.0271 (18)
C4—C5	1.378 (3)	C16—H16	0.9300
C4—H4	0.9300	C17—C21	1.405 (4)
C5—C6	1.373 (4)	C17—C18	1.417 (4)
C5—H5	0.9300	C17—Fe1	2.024 (2)
C6—C7	1.377 (3)	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.385 (3)
C7—C8	1.395 (3)	C18—Fe1	2.033 (2)
C7—H7	0.9300	C18—H18	0.9300
C8—C9	1.461 (2)	C19—C20	1.385 (4)
C9—C10	1.327 (2)	C19—Fe1	2.037 (2)
C9—H9	0.9300	C19—H19	0.9300
C10—C11	1.477 (2)	C20—C21	1.381 (4)
C10—H10	0.9300	C20—Fe1	2.037 (2)
C11—O3	1.225 (2)	C20—H20	0.9300
C11—C12	1.468 (2)	C21—Fe1	2.030 (2)
C12—C16	1.428 (3)	C21—H21	0.9300
C12—C13	1.428 (2)	O1—H1	0.8797
C12—Fe1	2.0234 (17)
O1—C1—C2	115.0 (2)	C18—C17—H17	126.2
O1—C1—H1A	108.5	Fe1—C17—H17	125.6
C2—C1—H1A	108.5	C19—C18—C17	107.0 (2)
O1—C1—H1B	108.5	C19—C18—Fe1	70.27 (13)
C2—C1—H1B	108.5	C17—C18—Fe1	69.23 (12)
H1A—C1—H1B	107.5	C19—C18—H18	126.5
O2—C2—C1	106.55 (19)	C17—C18—H18	126.5
O2—C2—H2A	110.4	Fe1—C18—H18	125.6
C1—C2—H2A	110.4	C20—C19—C18	109.0 (2)
O2—C2—H2B	110.4	C20—C19—Fe1	70.13 (12)
C1—C2—H2B	110.4	C18—C19—Fe1	69.93 (13)
H2A—C2—H2B	108.6	C20—C19—H19	125.5
O2—C3—C4	123.84 (18)	C18—C19—H19	125.5
O2—C3—C8	115.86 (15)	Fe1—C19—H19	126.0
C4—C3—C8	120.29 (19)	C21—C20—C19	108.6 (2)
C5—C4—C3	120.1 (2)	C21—C20—Fe1	69.88 (13)
C5—C4—H4	119.9	C19—C20—Fe1	70.12 (12)
C3—C4—H4	119.9	C21—C20—H20	125.7
C6—C5—C4	120.83 (19)	C19—C20—H20	125.7
C6—C5—H5	119.6	Fe1—C20—H20	125.9
C4—C5—H5	119.6	C20—C21—C17	107.8 (2)
C5—C6—C7	119.1 (2)	C20—C21—Fe1	70.42 (13)
C5—C6—H6	120.4	C17—C21—Fe1	69.49 (13)
C7—C6—H6	120.4	C20—C21—H21	126.1
C6—C7—C8	122.2 (2)	C17—C21—H21	126.1
C6—C7—H7	118.9	Fe1—C21—H21	125.6
C8—C7—H7	118.9	C1—O1—H1	109.00
C7—C8—C3	117.44 (17)	C3—O2—C2	119.45 (16)
C7—C8—C9	117.55 (16)	C12—Fe1—C17	123.79 (10)
C3—C8—C9	124.98 (16)	C12—Fe1—C16	41.28 (8)
C10—C9—C8	130.69 (16)	C17—Fe1—C16	160.08 (11)
C10—C9—H9	114.7	C12—Fe1—C21	160.77 (10)
C8—C9—H9	114.7	C17—Fe1—C21	40.55 (11)
C9—C10—C11	120.68 (15)	C16—Fe1—C21	157.08 (11)
C9—C10—H10	119.7	C12—Fe1—C18	107.13 (8)
C11—C10—H10	119.7	C17—Fe1—C18	40.89 (11)
O3—C11—C12	119.67 (16)	C16—Fe1—C18	122.76 (9)
O3—C11—C10	122.17 (15)	C21—Fe1—C18	68.19 (10)
C12—C11—C10	118.15 (15)	C12—Fe1—C20	157.48 (9)
C16—C12—C13	107.29 (15)	C17—Fe1—C20	67.31 (11)
C16—C12—C11	128.45 (16)	C16—Fe1—C20	121.80 (10)
C13—C12—C11	123.87 (16)	C21—Fe1—C20	39.70 (11)
C16—C12—Fe1	69.50 (10)	C18—Fe1—C20	67.32 (10)
C13—C12—Fe1	70.17 (10)	C12—Fe1—C19	122.09 (9)
C11—C12—Fe1	120.02 (11)	C17—Fe1—C19	67.37 (11)
C14—C13—C12	108.35 (18)	C16—Fe1—C19	107.33 (10)
C14—C13—Fe1	70.47 (12)	C21—Fe1—C19	67.07 (10)
C12—C13—Fe1	68.71 (10)	C18—Fe1—C19	39.81 (10)
C14—C13—H13	125.8	C20—Fe1—C19	39.75 (10)
C12—C13—H13	125.8	C12—Fe1—C13	41.12 (7)
Fe1—C13—H13	126.6	C17—Fe1—C13	108.66 (9)
C15—C14—C13	107.80 (17)	C16—Fe1—C13	68.82 (8)
C15—C14—Fe1	69.64 (12)	C21—Fe1—C13	124.62 (9)
C13—C14—Fe1	69.33 (11)	C18—Fe1—C13	123.29 (9)
C15—C14—H14	126.1	C20—Fe1—C13	160.23 (9)
C13—C14—H14	126.1	C19—Fe1—C13	158.58 (9)
Fe1—C14—H14	126.5	C12—Fe1—C15	68.40 (8)
C14—C15—C16	109.06 (18)	C17—Fe1—C15	158.41 (11)
C14—C15—Fe1	70.27 (11)	C16—Fe1—C15	40.51 (7)
C16—C15—Fe1	68.89 (10)	C21—Fe1—C15	122.65 (10)
C14—C15—H15	125.5	C18—Fe1—C15	159.19 (11)
C16—C15—H15	125.5	C20—Fe1—C15	108.56 (10)
Fe1—C15—H15	127.0	C19—Fe1—C15	124.01 (11)
C15—C16—C12	107.48 (18)	C13—Fe1—C15	67.59 (9)
C15—C16—Fe1	70.60 (11)	C12—Fe1—C14	68.62 (7)
C12—C16—Fe1	69.22 (9)	C17—Fe1—C14	123.28 (11)
C15—C16—H16	126.3	C16—Fe1—C14	68.40 (9)
C12—C16—H16	126.3	C21—Fe1—C14	108.71 (9)
Fe1—C16—H16	125.5	C18—Fe1—C14	159.13 (11)
C21—C17—C18	107.6 (2)	C20—Fe1—C14	124.38 (9)
C21—C17—Fe1	69.96 (13)	C19—Fe1—C14	159.79 (10)
C18—C17—Fe1	69.88 (12)	C13—Fe1—C14	40.20 (8)
C21—C17—H17	126.2	C15—Fe1—C14	40.09 (9)
O1—C1—C2—O2	56.9 (3)	C15—C16—Fe1—C14	−36.56 (14)
O2—C3—C4—C5	−177.42 (19)	C12—C16—Fe1—C14	81.76 (12)
C8—C3—C4—C5	0.9 (3)	C20—C21—Fe1—C12	−159.7 (2)
C3—C4—C5—C6	0.3 (3)	C17—C21—Fe1—C12	−41.1 (3)
C4—C5—C6—C7	−0.9 (4)	C20—C21—Fe1—C17	−118.6 (2)
C5—C6—C7—C8	0.3 (3)	C20—C21—Fe1—C16	43.1 (3)
C6—C7—C8—C3	0.9 (3)	C17—C21—Fe1—C16	161.7 (2)
C6—C7—C8—C9	−177.20 (19)	C20—C21—Fe1—C18	−80.31 (17)
O2—C3—C8—C7	177.02 (16)	C17—C21—Fe1—C18	38.30 (16)
C4—C3—C8—C7	−1.5 (3)	C17—C21—Fe1—C20	118.6 (2)
O2—C3—C8—C9	−5.1 (3)	C20—C21—Fe1—C19	−37.13 (16)
C4—C3—C8—C9	176.43 (17)	C17—C21—Fe1—C19	81.48 (17)
C7—C8—C9—C10	179.68 (19)	C20—C21—Fe1—C13	163.45 (14)
C3—C8—C9—C10	1.8 (3)	C17—C21—Fe1—C13	−77.94 (17)
C8—C9—C10—C11	−178.11 (16)	C20—C21—Fe1—C15	79.63 (17)
C9—C10—C11—O3	6.4 (3)	C17—C21—Fe1—C15	−161.76 (16)
C9—C10—C11—C12	−172.95 (16)	C20—C21—Fe1—C14	121.70 (15)
O3—C11—C12—C16	175.64 (18)	C17—C21—Fe1—C14	−119.69 (16)
C10—C11—C12—C16	−5.0 (3)	C19—C18—Fe1—C12	−119.90 (14)
O3—C11—C12—C13	−12.5 (3)	C17—C18—Fe1—C12	122.21 (15)
C10—C11—C12—C13	166.86 (16)	C19—C18—Fe1—C17	117.9 (2)
O3—C11—C12—Fe1	−97.67 (18)	C19—C18—Fe1—C16	−77.36 (17)
C10—C11—C12—Fe1	81.67 (18)	C17—C18—Fe1—C16	164.76 (15)
C16—C12—C13—C14	0.3 (2)	C19—C18—Fe1—C21	79.90 (17)
C11—C12—C13—C14	−173.01 (16)	C17—C18—Fe1—C21	−37.99 (16)
Fe1—C12—C13—C14	−59.52 (14)	C19—C18—Fe1—C20	36.86 (16)
C16—C12—C13—Fe1	59.86 (12)	C17—C18—Fe1—C20	−81.03 (17)
C11—C12—C13—Fe1	−113.49 (16)	C17—C18—Fe1—C19	−117.9 (2)
C12—C13—C14—C15	−0.8 (2)	C19—C18—Fe1—C13	−162.11 (14)
Fe1—C13—C14—C15	−59.22 (15)	C17—C18—Fe1—C13	80.01 (17)
C12—C13—C14—Fe1	58.43 (13)	C19—C18—Fe1—C15	−45.8 (3)
C13—C14—C15—C16	0.9 (2)	C17—C18—Fe1—C15	−163.6 (2)
Fe1—C14—C15—C16	−58.08 (15)	C19—C18—Fe1—C14	165.3 (2)
C13—C14—C15—Fe1	59.02 (14)	C17—C18—Fe1—C14	47.4 (3)
C14—C15—C16—C12	−0.7 (2)	C21—C20—Fe1—C12	162.6 (2)
Fe1—C15—C16—C12	−59.65 (13)	C19—C20—Fe1—C12	43.0 (3)
C14—C15—C16—Fe1	58.92 (15)	C21—C20—Fe1—C17	38.22 (16)
C13—C12—C16—C15	0.2 (2)	C19—C20—Fe1—C17	−81.40 (18)
C11—C12—C16—C15	173.19 (17)	C21—C20—Fe1—C16	−161.77 (14)
Fe1—C12—C16—C15	60.53 (14)	C19—C20—Fe1—C16	78.61 (18)
C13—C12—C16—Fe1	−60.29 (12)	C19—C20—Fe1—C21	−119.6 (2)
C11—C12—C16—Fe1	112.66 (17)	C21—C20—Fe1—C18	82.71 (17)
C21—C17—C18—C19	−0.4 (3)	C19—C20—Fe1—C18	−36.91 (16)
Fe1—C17—C18—C19	−60.44 (16)	C21—C20—Fe1—C19	119.6 (2)
C21—C17—C18—Fe1	60.05 (15)	C21—C20—Fe1—C13	−43.9 (3)
C17—C18—C19—C20	0.3 (3)	C19—C20—Fe1—C13	−163.5 (2)
Fe1—C18—C19—C20	−59.43 (17)	C21—C20—Fe1—C15	−119.11 (16)
C17—C18—C19—Fe1	59.78 (15)	C19—C20—Fe1—C15	121.27 (16)
C18—C19—C20—C21	−0.2 (3)	C21—C20—Fe1—C14	−77.54 (18)
Fe1—C19—C20—C21	−59.47 (16)	C19—C20—Fe1—C14	162.84 (15)
C18—C19—C20—Fe1	59.30 (16)	C20—C19—Fe1—C12	−162.04 (15)
C19—C20—C21—C17	−0.1 (3)	C18—C19—Fe1—C12	77.91 (17)
Fe1—C20—C21—C17	−59.70 (16)	C20—C19—Fe1—C17	81.24 (18)
C19—C20—C21—Fe1	59.62 (16)	C18—C19—Fe1—C17	−38.82 (16)
C18—C17—C21—C20	0.3 (3)	C20—C19—Fe1—C16	−119.22 (16)
Fe1—C17—C21—C20	60.29 (16)	C18—C19—Fe1—C16	120.73 (15)
C18—C17—C21—Fe1	−60.00 (15)	C20—C19—Fe1—C21	37.08 (17)
C4—C3—O2—C2	−14.0 (3)	C18—C19—Fe1—C21	−82.97 (17)
C8—C3—O2—C2	167.58 (17)	C20—C19—Fe1—C18	120.1 (2)
C1—C2—O2—C3	−179.56 (19)	C18—C19—Fe1—C20	−120.1 (2)
C16—C12—Fe1—C17	162.26 (14)	C20—C19—Fe1—C13	164.7 (2)
C13—C12—Fe1—C17	−79.57 (15)	C18—C19—Fe1—C13	44.7 (3)
C11—C12—Fe1—C17	38.85 (19)	C20—C19—Fe1—C15	−77.83 (18)
C13—C12—Fe1—C16	118.17 (15)	C18—C19—Fe1—C15	162.12 (14)
C11—C12—Fe1—C16	−123.41 (19)	C20—C19—Fe1—C14	−44.8 (3)
C16—C12—Fe1—C21	−166.8 (3)	C18—C19—Fe1—C14	−164.9 (2)
C13—C12—Fe1—C21	−48.6 (3)	C14—C13—Fe1—C12	119.78 (17)
C11—C12—Fe1—C21	69.8 (3)	C14—C13—Fe1—C17	−119.84 (15)
C16—C12—Fe1—C18	120.48 (13)	C12—C13—Fe1—C17	120.38 (14)
C13—C12—Fe1—C18	−121.35 (13)	C14—C13—Fe1—C16	81.19 (13)
C11—C12—Fe1—C18	−2.93 (17)	C12—C13—Fe1—C16	−38.59 (10)
C16—C12—Fe1—C20	48.6 (3)	C14—C13—Fe1—C21	−77.69 (16)
C13—C12—Fe1—C20	166.7 (2)	C12—C13—Fe1—C21	162.52 (13)
C11—C12—Fe1—C20	−74.9 (3)	C14—C13—Fe1—C18	−162.72 (14)
C16—C12—Fe1—C19	79.55 (14)	C12—C13—Fe1—C18	77.50 (14)
C13—C12—Fe1—C19	−162.28 (13)	C14—C13—Fe1—C20	−45.2 (3)
C11—C12—Fe1—C19	−43.86 (18)	C12—C13—Fe1—C20	−164.9 (3)
C16—C12—Fe1—C13	−118.17 (15)	C14—C13—Fe1—C19	164.7 (2)
C11—C12—Fe1—C13	118.42 (19)	C12—C13—Fe1—C19	44.9 (3)
C16—C12—Fe1—C15	−37.96 (12)	C14—C13—Fe1—C15	37.43 (12)
C13—C12—Fe1—C15	80.21 (12)	C12—C13—Fe1—C15	−82.36 (12)
C11—C12—Fe1—C15	−161.37 (17)	C12—C13—Fe1—C14	−119.78 (17)
C16—C12—Fe1—C14	−81.18 (13)	C14—C15—Fe1—C12	−82.03 (13)
C13—C12—Fe1—C14	36.99 (12)	C16—C15—Fe1—C12	38.66 (13)
C11—C12—Fe1—C14	155.40 (16)	C14—C15—Fe1—C17	46.7 (3)
C21—C17—Fe1—C12	164.90 (14)	C16—C15—Fe1—C17	167.3 (3)
C18—C17—Fe1—C12	−76.62 (16)	C14—C15—Fe1—C16	−120.69 (19)
C21—C17—Fe1—C16	−158.9 (3)	C14—C15—Fe1—C21	80.23 (16)
C18—C17—Fe1—C16	−40.5 (4)	C16—C15—Fe1—C21	−159.08 (15)
C18—C17—Fe1—C21	118.5 (2)	C14—C15—Fe1—C18	−163.4 (2)
C21—C17—Fe1—C18	−118.5 (2)	C16—C15—Fe1—C18	−42.7 (3)
C21—C17—Fe1—C20	−37.43 (15)	C14—C15—Fe1—C20	121.75 (14)
C18—C17—Fe1—C20	81.05 (16)	C16—C15—Fe1—C20	−117.56 (15)
C21—C17—Fe1—C19	−80.67 (17)	C14—C15—Fe1—C19	163.00 (13)
C18—C17—Fe1—C19	37.81 (14)	C16—C15—Fe1—C19	−76.31 (17)
C21—C17—Fe1—C13	121.85 (15)	C14—C15—Fe1—C13	−37.53 (12)
C18—C17—Fe1—C13	−119.67 (14)	C16—C15—Fe1—C13	83.16 (14)
C21—C17—Fe1—C15	45.7 (3)	C16—C15—Fe1—C14	120.69 (19)
C18—C17—Fe1—C15	164.2 (2)	C15—C14—Fe1—C12	81.45 (12)
C21—C17—Fe1—C14	79.81 (18)	C13—C14—Fe1—C12	−37.80 (11)
C18—C17—Fe1—C14	−161.71 (14)	C15—C14—Fe1—C17	−161.33 (14)
C15—C16—Fe1—C12	−118.31 (19)	C13—C14—Fe1—C17	79.42 (16)
C15—C16—Fe1—C17	−166.3 (3)	C15—C14—Fe1—C16	36.93 (12)
C12—C16—Fe1—C17	−48.0 (3)	C13—C14—Fe1—C16	−82.33 (12)
C15—C16—Fe1—C21	50.5 (3)	C15—C14—Fe1—C21	−118.83 (14)
C12—C16—Fe1—C21	168.9 (2)	C13—C14—Fe1—C21	121.91 (14)
C15—C16—Fe1—C18	163.34 (15)	C15—C14—Fe1—C18	163.5 (2)
C12—C16—Fe1—C18	−78.34 (15)	C13—C14—Fe1—C18	44.2 (3)
C15—C16—Fe1—C20	81.43 (17)	C15—C14—Fe1—C20	−77.64 (16)
C12—C16—Fe1—C20	−160.26 (12)	C13—C14—Fe1—C20	163.10 (13)
C15—C16—Fe1—C19	122.47 (15)	C15—C14—Fe1—C19	−44.6 (3)
C12—C16—Fe1—C19	−119.21 (12)	C13—C14—Fe1—C19	−163.8 (2)
C15—C16—Fe1—C13	−79.87 (15)	C15—C14—Fe1—C13	119.25 (17)
C12—C16—Fe1—C13	38.44 (10)	C13—C14—Fe1—C15	−119.25 (17)
C12—C16—Fe1—C15	118.31 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.88	1.98	2.841 (2)	165
C7—H7···O3ii	0.93	2.56	3.409 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.88	1.98	2.841 (2)	165
C7—H7⋯O3ii	0.93	2.56	3.409 (3)	152

Symmetry codes: (i) ; (ii) .