Triethylphosphine as a molecular gear — phase transitions in ferrocenyl–acetylide–gold(I)

A sequence of two discontinuous phase transitions, occurring just above 125 K and 148 K, has been observed for a ferrocenyl–acetylide–gold(I) complex with triethylphosphine, structure (1), by means of a multi-temperature single-crystal X-ray diffraction technique. Three distinct phases have been identified. The high-temperature α and low-temperature γ phases share the same space group Pbca, whereas the intermediate β phase is in the Pb2₁a subgroup of Pbca. In all phases molecules of (1) form well defined double layers, with PEt₃ groups interlocking in planes perpendicular to c. On the molecular level, both phase transitions involve almost uniquely a conformational change of triethylphosphine: a gear-like rotation around the P—Au axis and concerted flips of the ethyl moieties. The mechanism of these transitions may be imagined as initiated by a rotation of a single PEt₃ group in a double layer (a single gear movement), followed by adjacent phosphines adjusting their conformations as a result of steric strain. The structural changes underlying phase transitions are sequential, occurring layer-wise, the γ→β transition involving approximately every other layer in the crystal lattice, the β→α yielding a total conformation change. The sequence of phase transitions results in a noticeable contraction of the crystal cell volume.

Computing details

Data collection: APEX2 v2012.4-3 (Bruker AXS) for 1-125k, 1-140k, 1-200k. Cell refinement: SAINT v8.34A (Bruker, 2013) for 1-110k, 1-200k; APEX2 v2012.4-3 (Bruker AXS) for 1-125k, 1-140k. Data reduction: SAINT v8.34A (Bruker, 2013) for 1-110k, 1-200k; SAINT V8.18C (Bruker AXS Inc., 2011) for 1-125k, 1-140k. Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for 1-125k, 1-140k; SHELXS (Sheldrick, 2008) for 1-200k. For all structures, program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(1-110k)

Crystal data

C18H24AuFeP	Dx = 1.952 Mg m^−3
Mr = 524.16	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9928 reflections
a = 13.8822 (17) Å	θ = 2.5–28.2°
b = 11.6188 (14) Å	µ = 9.11 mm^−1
c = 22.115 (3) Å	T = 110 K
V = 3567.0 (8) Å^3	Block, clear reddish brown
Z = 8	0.22 × 0.17 × 0.12 mm
F(000) = 2016

Data collection

Bruker APEX-II CCD diffractometer	3930 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.036
Absorption correction: multi-scan SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1149 before and 0.0801 after correction. The Ratio of minimum to maximum transmission is 0.5166. The λ/2 correction factor is 0.0015.	θmax = 29.1°, θmin = 1.8°
Tmin = 0.285, Tmax = 0.552	h = −19→18
26682 measured reflections	k = −11→15
4788 independent reflections	l = −30→30

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.020	H-atom parameters constrained
wR(F^2) = 0.044	w = 1/[σ^2(Fo^2) + (0.0159P)^2 + 3.7283P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
4788 reflections	Δρmax = 1.21 e Å^−3
193 parameters	Δρmin = −0.67 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Au1	0.41722 (2)	0.27011 (2)	0.34482 (2)	0.01689 (4)
Fe1	0.31732 (3)	−0.15453 (3)	0.49451 (2)	0.01342 (8)
P1	0.42580 (5)	0.44173 (6)	0.29546 (3)	0.01698 (14)
C1	0.39673 (18)	−0.0992 (2)	0.42235 (12)	0.0160 (5)
C2	0.45678 (19)	−0.1550 (2)	0.46636 (12)	0.0176 (5)
H2	0.5099	−0.1211	0.4868	0.021*
C3	0.4231 (2)	−0.2698 (2)	0.47417 (13)	0.0215 (6)
H3	0.4498	−0.3258	0.5006	0.026*
C4	0.3423 (2)	−0.2857 (2)	0.43533 (13)	0.0224 (6)
H4	0.3056	−0.3542	0.4314	0.027*
C5	0.3262 (2)	−0.1817 (2)	0.40351 (12)	0.0197 (6)
H5	0.2769	−0.1688	0.3745	0.024*
C6	0.26888 (19)	−0.0100 (2)	0.53648 (13)	0.0208 (6)
H6	0.2850	0.0668	0.5258	0.025*
C7	0.3198 (2)	−0.0806 (3)	0.57786 (12)	0.0224 (6)
H7	0.3757	−0.0595	0.6000	0.027*
C8	0.2721 (2)	−0.1885 (3)	0.58017 (13)	0.0246 (6)
H8	0.2909	−0.2526	0.6041	0.029*
C9	0.1922 (2)	−0.1843 (3)	0.54102 (14)	0.0243 (6)
H9	0.1476	−0.2449	0.5340	0.029*
C10	0.1901 (2)	−0.0735 (2)	0.51398 (14)	0.0224 (6)
H10	0.1438	−0.0468	0.4857	0.027*
C11	0.40337 (19)	0.0179 (3)	0.40202 (11)	0.0177 (6)
C12	0.40885 (19)	0.1144 (3)	0.38307 (12)	0.0192 (6)
C13	0.5163 (2)	0.5406 (3)	0.32452 (15)	0.0294 (7)
H13A	0.5231	0.6062	0.2963	0.035*
H13B	0.4946	0.5713	0.3640	0.035*
C14	0.6133 (2)	0.4833 (4)	0.33244 (17)	0.0419 (9)
H14A	0.6073	0.4193	0.3611	0.063*
H14B	0.6597	0.5394	0.3481	0.063*
H14C	0.6357	0.4540	0.2933	0.063*
C15	0.3140 (2)	0.5230 (3)	0.29539 (13)	0.0246 (6)
H15A	0.2630	0.4742	0.2775	0.030*
H15B	0.2956	0.5385	0.3379	0.030*
C16	0.3156 (3)	0.6375 (3)	0.26136 (15)	0.0354 (8)
H16A	0.3661	0.6870	0.2782	0.053*
H16B	0.2530	0.6757	0.2656	0.053*
H16C	0.3288	0.6234	0.2185	0.053*
C17	0.4580 (2)	0.4218 (3)	0.21635 (12)	0.0209 (6)
H17A	0.4643	0.4983	0.1970	0.025*
H17B	0.5216	0.3834	0.2142	0.025*
C18	0.3853 (2)	0.3508 (3)	0.18085 (13)	0.0245 (6)
H18A	0.3734	0.2781	0.2020	0.037*
H18B	0.4109	0.3349	0.1404	0.037*
H18C	0.3249	0.3938	0.1773	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.01714 (5)	0.01655 (6)	0.01698 (5)	−0.00181 (4)	0.00040 (4)	0.00325 (4)
Fe1	0.01328 (17)	0.01105 (18)	0.01592 (17)	−0.00005 (14)	0.00065 (14)	0.00001 (15)
P1	0.0179 (3)	0.0156 (4)	0.0174 (3)	−0.0036 (3)	−0.0023 (3)	0.0018 (3)
C1	0.0158 (13)	0.0171 (14)	0.0150 (12)	0.0016 (10)	0.0030 (10)	−0.0018 (11)
C2	0.0142 (12)	0.0204 (15)	0.0183 (13)	0.0053 (11)	0.0022 (10)	−0.0010 (11)
C3	0.0262 (15)	0.0163 (14)	0.0220 (13)	0.0081 (12)	0.0033 (11)	0.0012 (11)
C4	0.0332 (16)	0.0122 (15)	0.0218 (14)	−0.0009 (12)	0.0018 (12)	−0.0056 (11)
C5	0.0248 (15)	0.0183 (15)	0.0161 (12)	−0.0013 (12)	−0.0020 (10)	−0.0011 (11)
C6	0.0223 (14)	0.0130 (14)	0.0273 (14)	−0.0002 (11)	0.0103 (11)	−0.0009 (12)
C7	0.0228 (14)	0.0270 (17)	0.0172 (13)	−0.0002 (12)	0.0062 (11)	−0.0066 (12)
C8	0.0282 (16)	0.0220 (15)	0.0236 (14)	0.0066 (12)	0.0108 (12)	0.0066 (13)
C9	0.0174 (14)	0.0171 (15)	0.0385 (17)	−0.0008 (11)	0.0088 (12)	0.0010 (13)
C10	0.0176 (13)	0.0165 (14)	0.0330 (16)	0.0056 (11)	0.0043 (12)	0.0033 (13)
C11	0.0174 (13)	0.0227 (15)	0.0128 (12)	−0.0009 (11)	0.0027 (10)	−0.0003 (11)
C12	0.0160 (13)	0.0213 (15)	0.0205 (13)	−0.0017 (11)	0.0014 (11)	−0.0009 (12)
C13	0.0290 (16)	0.0253 (17)	0.0339 (16)	−0.0090 (13)	−0.0087 (13)	0.0002 (14)
C14	0.0232 (16)	0.052 (3)	0.050 (2)	−0.0096 (16)	−0.0070 (15)	−0.0072 (19)
C15	0.0268 (15)	0.0257 (17)	0.0212 (14)	0.0049 (13)	0.0007 (12)	−0.0024 (13)
C16	0.048 (2)	0.0253 (18)	0.0329 (17)	0.0163 (15)	−0.0012 (15)	0.0039 (14)
C17	0.0208 (14)	0.0216 (16)	0.0204 (13)	−0.0014 (12)	0.0038 (11)	0.0036 (12)
C18	0.0298 (15)	0.0247 (17)	0.0189 (13)	0.0010 (13)	0.0010 (12)	−0.0019 (13)

Geometric parameters (Å, º)

Au1—P1	2.2764 (8)	C6—C10	1.410 (4)
Au1—C12	2.000 (3)	C7—H7	0.9500
Fe1—C1	2.043 (3)	C7—C8	1.419 (4)
Fe1—C2	2.034 (3)	C8—H8	0.9500
Fe1—C3	2.038 (3)	C8—C9	1.409 (4)
Fe1—C4	2.038 (3)	C9—H9	0.9500
Fe1—C5	2.041 (3)	C9—C10	1.420 (4)
Fe1—C6	2.033 (3)	C10—H10	0.9500
Fe1—C7	2.034 (3)	C11—C12	1.200 (4)
Fe1—C8	2.034 (3)	C13—H13A	0.9900
Fe1—C9	2.049 (3)	C13—H13B	0.9900
Fe1—C10	2.047 (3)	C13—C14	1.512 (5)
P1—C13	1.820 (3)	C14—H14A	0.9800
P1—C15	1.817 (3)	C14—H14B	0.9800
P1—C17	1.821 (3)	C14—H14C	0.9800
C1—C2	1.436 (4)	C15—H15A	0.9900
C1—C5	1.432 (4)	C15—H15B	0.9900
C1—C11	1.435 (4)	C15—C16	1.528 (4)
C2—H2	0.9500	C16—H16A	0.9800
C2—C3	1.424 (4)	C16—H16B	0.9800
C3—H3	0.9500	C16—H16C	0.9800
C3—C4	1.424 (4)	C17—H17A	0.9900
C4—H4	0.9500	C17—H17B	0.9900
C4—C5	1.416 (4)	C17—C18	1.521 (4)
C5—H5	0.9500	C18—H18A	0.9800
C6—H6	0.9500	C18—H18B	0.9800
C6—C7	1.418 (4)	C18—H18C	0.9800
C12—Au1—P1	176.35 (8)	C5—C4—H4	125.9
C1—Fe1—C9	154.54 (12)	Fe1—C5—H5	126.7
C1—Fe1—C10	119.01 (11)	C1—C5—Fe1	69.57 (15)
C2—Fe1—C1	41.24 (10)	C1—C5—H5	125.7
C2—Fe1—C3	40.95 (11)	C4—C5—Fe1	69.60 (16)
C2—Fe1—C4	68.86 (12)	C4—C5—C1	108.6 (2)
C2—Fe1—C5	68.92 (11)	C4—C5—H5	125.7
C2—Fe1—C7	105.20 (11)	Fe1—C6—H6	125.7
C2—Fe1—C8	125.32 (12)	C7—C6—Fe1	69.62 (16)
C2—Fe1—C9	163.88 (12)	C7—C6—H6	125.9
C2—Fe1—C10	152.47 (12)	C10—C6—Fe1	70.29 (16)
C3—Fe1—C1	69.24 (11)	C10—C6—H6	125.9
C3—Fe1—C4	40.91 (12)	C10—C6—C7	108.1 (3)
C3—Fe1—C5	68.73 (12)	Fe1—C7—H7	126.2
C3—Fe1—C9	127.66 (12)	C6—C7—Fe1	69.58 (16)
C3—Fe1—C10	166.03 (12)	C6—C7—H7	126.2
C4—Fe1—C1	69.01 (11)	C6—C7—C8	107.6 (3)
C4—Fe1—C5	40.62 (12)	C8—C7—Fe1	69.60 (16)
C4—Fe1—C9	109.92 (12)	C8—C7—H7	126.2
C4—Fe1—C10	128.75 (12)	Fe1—C8—H8	125.8
C5—Fe1—C1	41.06 (11)	C7—C8—Fe1	69.58 (16)
C5—Fe1—C9	121.35 (12)	C7—C8—H8	125.8
C5—Fe1—C10	109.31 (12)	C9—C8—Fe1	70.37 (17)
C6—Fe1—C1	105.96 (11)	C9—C8—C7	108.4 (3)
C6—Fe1—C2	117.16 (11)	C9—C8—H8	125.8
C6—Fe1—C3	151.88 (12)	Fe1—C9—H9	126.6
C6—Fe1—C4	165.20 (12)	C8—C9—Fe1	69.27 (16)
C6—Fe1—C5	126.71 (12)	C8—C9—H9	126.1
C6—Fe1—C7	40.80 (12)	C8—C9—C10	107.8 (3)
C6—Fe1—C8	68.48 (12)	C10—C9—Fe1	69.64 (16)
C6—Fe1—C9	68.28 (11)	C10—C9—H9	126.1
C6—Fe1—C10	40.43 (11)	Fe1—C10—H10	126.6
C7—Fe1—C1	124.44 (12)	C6—C10—Fe1	69.28 (16)
C7—Fe1—C3	117.73 (12)	C6—C10—C9	108.1 (3)
C7—Fe1—C4	153.47 (12)	C6—C10—H10	125.9
C7—Fe1—C5	163.32 (12)	C9—C10—Fe1	69.79 (16)
C7—Fe1—C8	40.82 (12)	C9—C10—H10	125.9
C7—Fe1—C9	68.33 (12)	C12—C11—C1	177.8 (3)
C7—Fe1—C10	68.27 (12)	C11—C12—Au1	175.4 (3)
C8—Fe1—C1	162.69 (12)	P1—C13—H13A	109.2
C8—Fe1—C3	107.48 (12)	P1—C13—H13B	109.2
C8—Fe1—C4	120.37 (12)	H13A—C13—H13B	107.9
C8—Fe1—C5	155.10 (12)	C14—C13—P1	112.2 (2)
C8—Fe1—C9	40.36 (12)	C14—C13—H13A	109.2
C8—Fe1—C10	68.11 (12)	C14—C13—H13B	109.2
C10—Fe1—C9	40.58 (11)	C13—C14—H14A	109.5
C13—P1—Au1	114.81 (11)	C13—C14—H14B	109.5
C13—P1—C17	104.49 (14)	C13—C14—H14C	109.5
C15—P1—Au1	114.28 (10)	H14A—C14—H14B	109.5
C15—P1—C13	105.20 (15)	H14A—C14—H14C	109.5
C15—P1—C17	105.96 (13)	H14B—C14—H14C	109.5
C17—P1—Au1	111.23 (10)	P1—C15—H15A	108.3
C2—C1—Fe1	69.01 (15)	P1—C15—H15B	108.3
C5—C1—Fe1	69.37 (15)	H15A—C15—H15B	107.4
C5—C1—C2	107.0 (2)	C16—C15—P1	116.1 (2)
C5—C1—C11	125.9 (2)	C16—C15—H15A	108.3
C11—C1—Fe1	125.26 (19)	C16—C15—H15B	108.3
C11—C1—C2	127.1 (2)	C15—C16—H16A	109.5
Fe1—C2—H2	126.3	C15—C16—H16B	109.5
C1—C2—Fe1	69.74 (15)	C15—C16—H16C	109.5
C1—C2—H2	125.8	H16A—C16—H16B	109.5
C3—C2—Fe1	69.68 (15)	H16A—C16—H16C	109.5
C3—C2—C1	108.3 (2)	H16B—C16—H16C	109.5
C3—C2—H2	125.8	P1—C17—H17A	108.8
Fe1—C3—H3	126.6	P1—C17—H17B	108.8
C2—C3—Fe1	69.37 (15)	H17A—C17—H17B	107.7
C2—C3—H3	126.1	C18—C17—P1	113.73 (19)
C4—C3—Fe1	69.57 (16)	C18—C17—H17A	108.8
C4—C3—C2	107.8 (2)	C18—C17—H17B	108.8
C4—C3—H3	126.1	C17—C18—H18A	109.5
Fe1—C4—H4	126.4	C17—C18—H18B	109.5
C3—C4—Fe1	69.52 (16)	C17—C18—H18C	109.5
C3—C4—H4	125.9	H18A—C18—H18B	109.5
C5—C4—Fe1	69.78 (16)	H18A—C18—H18C	109.5
C5—C4—C3	108.3 (3)	H18B—C18—H18C	109.5
Au1—P1—C13—C14	48.8 (3)	C5—C1—C2—C3	0.0 (3)
Au1—P1—C15—C16	−178.5 (2)	C6—C7—C8—Fe1	59.45 (19)
Au1—P1—C17—C18	61.5 (2)	C6—C7—C8—C9	−0.4 (3)
Fe1—C1—C2—C3	59.19 (18)	C7—C6—C10—Fe1	−59.55 (19)
Fe1—C1—C5—C4	−58.84 (19)	C7—C6—C10—C9	−0.4 (3)
Fe1—C2—C3—C4	59.13 (19)	C7—C8—C9—Fe1	59.41 (19)
Fe1—C3—C4—C5	59.20 (19)	C7—C8—C9—C10	0.2 (3)
Fe1—C4—C5—C1	58.82 (19)	C8—C9—C10—Fe1	59.0 (2)
Fe1—C6—C7—C8	−59.47 (19)	C8—C9—C10—C6	0.1 (3)
Fe1—C6—C10—C9	59.2 (2)	C10—C6—C7—Fe1	60.0 (2)
Fe1—C7—C8—C9	−59.9 (2)	C10—C6—C7—C8	0.5 (3)
Fe1—C8—C9—C10	−59.2 (2)	C11—C1—C2—Fe1	119.0 (3)
Fe1—C9—C10—C6	−58.87 (19)	C11—C1—C2—C3	178.2 (2)
C1—C2—C3—Fe1	−59.23 (18)	C11—C1—C5—Fe1	−119.3 (3)
C1—C2—C3—C4	−0.1 (3)	C11—C1—C5—C4	−178.1 (3)
C2—C1—C5—Fe1	59.00 (18)	C13—P1—C15—C16	54.7 (3)
C2—C1—C5—C4	0.2 (3)	C13—P1—C17—C18	−174.1 (2)
C2—C3—C4—Fe1	−59.01 (18)	C15—P1—C13—C14	175.3 (2)
C2—C3—C4—C5	0.2 (3)	C15—P1—C17—C18	−63.3 (2)
C3—C4—C5—Fe1	−59.04 (19)	C17—P1—C13—C14	−73.3 (3)
C3—C4—C5—C1	−0.2 (3)	C17—P1—C15—C16	−55.7 (3)
C5—C1—C2—Fe1	−59.23 (18)

(1-125k)

Crystal data

C18H24AuFeP	Dx = 1.950 Mg m^−3
Mr = 524.16	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9928 reflections
a = 13.8732 (18) Å	θ = 2.5–28.2°
b = 11.6316 (15) Å	µ = 9.10 mm^−1
c = 22.124 (3) Å	T = 125 K
V = 3570.0 (8) Å^3	Block, clear reddish brown
Z = 8	0.22 × 0.17 × 0.12 mm
F(000) = 2016

Data collection

Bruker kappa APEX2 area detector diffractometer	4687 independent reflections
Radiation source: rotating anode X-ray tube, Bruker TXS	3902 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.046
Detector resolution: 7.9 pixels mm^-1	θmax = 28.9°, θmin = 1.8°
ω and φ scans	h = −18→17
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS Inc.)	k = −11→15
Tmin = 0.303, Tmax = 0.552	l = −30→29
26121 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + 34.2581P] where P = (Fo^2 + 2Fc^2)/3
S = 1.26	(Δ/σ)max = 0.001
4687 reflections	Δρmax = 2.32 e Å^−3
193 parameters	Δρmin = −3.23 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Au1	0.41732 (2)	0.27016 (2)	0.34450 (2)	0.01974 (7)
Fe1	0.31733 (6)	−0.15398 (7)	0.49401 (4)	0.01480 (17)
P1	0.42632 (13)	0.44146 (14)	0.29514 (7)	0.0204 (3)
C1	0.3966 (4)	−0.0982 (5)	0.4219 (3)	0.0186 (13)
C2	0.4562 (5)	−0.1545 (6)	0.4662 (3)	0.0206 (13)
H2	0.5089	−0.1204	0.4870	0.025*
C3	0.4237 (5)	−0.2685 (6)	0.4738 (3)	0.0257 (14)
H3	0.4508	−0.3243	0.5002	0.031*
C4	0.3426 (5)	−0.2851 (6)	0.4348 (3)	0.0257 (14)
H4	0.3060	−0.3537	0.4308	0.031*
C5	0.3269 (5)	−0.1810 (6)	0.4030 (3)	0.0243 (14)
H5	0.2778	−0.1684	0.3739	0.029*
C6	0.2688 (5)	−0.0095 (6)	0.5360 (3)	0.0231 (14)
H6	0.2847	0.0673	0.5254	0.028*
C7	0.3197 (5)	−0.0800 (6)	0.5772 (3)	0.0250 (14)
H7	0.3757	−0.0590	0.5993	0.030*
C8	0.2719 (5)	−0.1878 (6)	0.5796 (3)	0.0281 (15)
H8	0.2906	−0.2517	0.6037	0.034*
C9	0.1922 (5)	−0.1842 (6)	0.5404 (3)	0.0286 (16)
H9	0.1479	−0.2452	0.5334	0.034*
C10	0.1892 (5)	−0.0744 (6)	0.5131 (3)	0.0273 (15)
H10	0.1427	−0.0484	0.4847	0.033*
C11	0.4030 (4)	0.0184 (6)	0.4018 (3)	0.0196 (13)
C12	0.4090 (5)	0.1155 (6)	0.3828 (3)	0.0220 (13)
C13	0.5165 (6)	0.5400 (7)	0.3245 (4)	0.0360 (18)
H13A	0.5229	0.6060	0.2966	0.043*
H13B	0.4948	0.5699	0.3641	0.043*
C14	0.6134 (6)	0.4835 (9)	0.3320 (4)	0.050 (2)
H14A	0.6082	0.4204	0.3611	0.075*
H14B	0.6601	0.5401	0.3467	0.075*
H14C	0.6350	0.4531	0.2929	0.075*
C15	0.3142 (5)	0.5228 (6)	0.2950 (3)	0.0293 (15)
H15A	0.2633	0.4743	0.2768	0.035*
H15B	0.2955	0.5379	0.3375	0.035*
C16	0.3166 (7)	0.6371 (7)	0.2614 (4)	0.042 (2)
H16A	0.3645	0.6878	0.2801	0.063*
H16B	0.2529	0.6733	0.2633	0.063*
H16C	0.3340	0.6236	0.2190	0.063*
C17	0.4580 (5)	0.4211 (6)	0.2165 (3)	0.0243 (14)
H17A	0.4646	0.4974	0.1971	0.029*
H17B	0.5214	0.3824	0.2143	0.029*
C18	0.3852 (5)	0.3507 (6)	0.1810 (3)	0.0279 (15)
H18A	0.3739	0.2774	0.2017	0.042*
H18B	0.4103	0.3359	0.1403	0.042*
H18C	0.3245	0.3933	0.1780	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.02044 (12)	0.01888 (11)	0.01991 (11)	−0.00158 (10)	0.00027 (10)	0.00409 (9)
Fe1	0.0137 (4)	0.0121 (4)	0.0187 (4)	−0.0004 (3)	0.0006 (3)	−0.0003 (3)
P1	0.0220 (8)	0.0180 (8)	0.0211 (7)	−0.0040 (7)	−0.0031 (7)	0.0022 (6)
C1	0.017 (3)	0.020 (3)	0.019 (3)	0.004 (2)	0.005 (2)	0.000 (2)
C2	0.019 (3)	0.020 (3)	0.023 (3)	0.005 (2)	0.001 (2)	−0.001 (3)
C3	0.031 (3)	0.020 (3)	0.027 (3)	0.013 (3)	0.007 (3)	0.001 (3)
C4	0.038 (4)	0.015 (3)	0.024 (3)	0.001 (3)	0.002 (3)	−0.006 (3)
C5	0.029 (4)	0.023 (3)	0.020 (3)	−0.001 (3)	−0.002 (3)	−0.003 (3)
C6	0.022 (4)	0.016 (3)	0.032 (3)	0.001 (3)	0.010 (3)	−0.002 (3)
C7	0.029 (4)	0.025 (3)	0.021 (3)	0.001 (3)	0.006 (3)	−0.010 (3)
C8	0.032 (4)	0.024 (3)	0.028 (3)	0.007 (3)	0.012 (3)	0.010 (3)
C9	0.019 (3)	0.019 (3)	0.048 (4)	−0.002 (3)	0.013 (3)	0.001 (3)
C10	0.022 (3)	0.017 (3)	0.044 (4)	0.008 (3)	0.007 (3)	0.002 (3)
C11	0.016 (3)	0.026 (3)	0.016 (3)	−0.003 (3)	0.003 (2)	0.000 (2)
C12	0.017 (3)	0.029 (3)	0.019 (3)	−0.001 (3)	0.003 (3)	0.000 (3)
C13	0.034 (4)	0.033 (4)	0.041 (4)	−0.010 (3)	−0.012 (3)	0.000 (3)
C14	0.030 (4)	0.059 (6)	0.062 (6)	−0.009 (4)	−0.008 (4)	−0.007 (5)
C15	0.032 (4)	0.028 (4)	0.028 (3)	0.004 (3)	0.000 (3)	−0.004 (3)
C16	0.054 (6)	0.031 (4)	0.039 (4)	0.017 (4)	0.000 (4)	0.004 (3)
C17	0.022 (3)	0.026 (4)	0.024 (3)	−0.001 (3)	0.006 (3)	0.004 (3)
C18	0.036 (4)	0.023 (3)	0.024 (3)	0.002 (3)	−0.004 (3)	−0.003 (3)

Geometric parameters (Å, º)

Au1—P1	2.2756 (16)	C1—C2	1.441 (9)
Au1—C12	1.992 (7)	C1—C5	1.427 (9)
Fe1—C1	2.044 (6)	C1—C11	1.430 (9)
Fe1—C2	2.023 (6)	C2—C3	1.410 (10)
Fe1—C3	2.038 (6)	C3—C4	1.432 (10)
Fe1—C4	2.041 (6)	C4—C5	1.416 (9)
Fe1—C5	2.041 (6)	C6—C7	1.416 (10)
Fe1—C6	2.035 (6)	C6—C10	1.430 (10)
Fe1—C7	2.033 (6)	C7—C8	1.419 (10)
Fe1—C8	2.035 (6)	C8—C9	1.407 (10)
Fe1—C9	2.047 (7)	C9—C10	1.413 (10)
Fe1—C10	2.048 (7)	C11—C12	1.208 (9)
P1—C13	1.817 (8)	C13—C14	1.506 (12)
P1—C15	1.820 (7)	C15—C16	1.524 (10)
P1—C17	1.810 (7)	C17—C18	1.519 (10)
C12—Au1—P1	176.49 (19)	C9—Fe1—C10	40.4 (3)
C1—Fe1—C9	154.5 (3)	C13—P1—Au1	114.7 (3)
C1—Fe1—C10	119.0 (3)	C13—P1—C15	105.1 (4)
C2—Fe1—C1	41.5 (2)	C15—P1—Au1	114.1 (3)
C2—Fe1—C3	40.6 (3)	C17—P1—Au1	111.1 (2)
C2—Fe1—C4	68.8 (3)	C17—P1—C13	105.0 (4)
C2—Fe1—C5	68.8 (3)	C17—P1—C15	105.9 (3)
C2—Fe1—C6	117.2 (3)	C2—C1—Fe1	68.5 (4)
C2—Fe1—C7	105.2 (3)	C5—C1—Fe1	69.5 (4)
C2—Fe1—C8	125.3 (3)	C5—C1—C2	106.3 (6)
C2—Fe1—C9	163.7 (3)	C5—C1—C11	126.2 (6)
C2—Fe1—C10	153.0 (3)	C11—C1—Fe1	125.2 (4)
C3—Fe1—C1	69.3 (3)	C11—C1—C2	127.4 (6)
C3—Fe1—C4	41.1 (3)	C1—C2—Fe1	70.0 (4)
C3—Fe1—C5	68.7 (3)	C3—C2—Fe1	70.2 (4)
C3—Fe1—C9	127.7 (3)	C3—C2—C1	109.0 (6)
C3—Fe1—C10	165.8 (3)	C2—C3—Fe1	69.1 (4)
C4—Fe1—C1	69.1 (3)	C2—C3—C4	107.8 (6)
C4—Fe1—C9	109.8 (3)	C4—C3—Fe1	69.6 (4)
C4—Fe1—C10	128.3 (3)	C3—C4—Fe1	69.3 (4)
C5—Fe1—C1	40.9 (3)	C5—C4—Fe1	69.7 (4)
C5—Fe1—C4	40.6 (3)	C5—C4—C3	107.7 (6)
C5—Fe1—C9	121.5 (3)	C1—C5—Fe1	69.6 (3)
C5—Fe1—C10	109.2 (3)	C4—C5—Fe1	69.7 (4)
C6—Fe1—C1	105.8 (3)	C4—C5—C1	109.1 (6)
C6—Fe1—C3	151.6 (3)	C7—C6—Fe1	69.6 (4)
C6—Fe1—C4	165.2 (3)	C7—C6—C10	107.9 (6)
C6—Fe1—C5	126.8 (3)	C10—C6—Fe1	70.0 (4)
C6—Fe1—C8	68.4 (3)	C6—C7—Fe1	69.7 (4)
C6—Fe1—C9	68.4 (3)	C6—C7—C8	107.6 (6)
C6—Fe1—C10	41.0 (3)	C8—C7—Fe1	69.7 (4)
C7—Fe1—C1	124.4 (3)	C7—C8—Fe1	69.5 (4)
C7—Fe1—C3	117.6 (3)	C9—C8—Fe1	70.3 (4)
C7—Fe1—C4	153.5 (3)	C9—C8—C7	108.5 (6)
C7—Fe1—C5	163.2 (3)	C8—C9—Fe1	69.4 (4)
C7—Fe1—C6	40.7 (3)	C8—C9—C10	108.3 (6)
C7—Fe1—C8	40.8 (3)	C10—C9—Fe1	69.9 (4)
C7—Fe1—C9	68.4 (3)	C6—C10—Fe1	69.0 (4)
C7—Fe1—C10	68.6 (3)	C9—C10—Fe1	69.8 (4)
C8—Fe1—C1	162.7 (3)	C9—C10—C6	107.7 (6)
C8—Fe1—C3	107.6 (3)	C12—C11—C1	177.7 (7)
C8—Fe1—C4	120.4 (3)	C11—C12—Au1	175.2 (6)
C8—Fe1—C5	155.2 (3)	C14—C13—P1	112.3 (6)
C8—Fe1—C9	40.3 (3)	C16—C15—P1	115.8 (6)
C8—Fe1—C10	68.1 (3)	C18—C17—P1	114.0 (5)

(1-140k)

Crystal data

C18H24AuFeP	Dx = 1.963 Mg m^−3
Mr = 524.16	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pb21a	Cell parameters from 9928 reflections
a = 13.872 (18) Å	θ = 2.5–28.2°
b = 11.644 (16) Å	µ = 9.16 mm^−1
c = 21.96 (3) Å	T = 140 K
V = 3548 (8) Å^3	Block, clear reddish brown
Z = 8	0.22 × 0.17 × 0.12 mm
F(000) = 2016

Data collection

Bruker kappa APEX2 area detector diffractometer	7862 independent reflections
Radiation source: rotating anode X-ray tube, Bruker TXS	7010 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.066
Detector resolution: 7.9 pixels mm^-1	θmax = 28.3°, θmin = 0.9°
ω and φ scans	h = −18→17
Absorption correction: multi-scan SADABS V2008/1 (Bruker AXS Inc.)	k = −11→15
Tmin = 0.285, Tmax = 0.552	l = −29→29
23957 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.086	w = 1/[σ^2(Fo^2) + (0.0001P)^2 + 360.9662P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.214	(Δ/σ)max = 0.001
S = 1.13	Δρmax = 8.55 e Å^−3
7862 reflections	Δρmin = −6.76 e Å^−3
386 parameters	Absolute structure: Refined as an inversion twin.
493 restraints	Absolute structure parameter: 0.45 (3)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Au1	0.44740 (7)	0.76617 (11)	0.40498 (5)	0.0174 (3)
Fe1	0.3089 (3)	0.3430 (4)	0.2620 (2)	0.0171 (8)
P1	0.4994 (5)	0.9310 (7)	0.4501 (3)	0.0154 (13)
C1	0.386 (2)	0.399 (3)	0.3355 (14)	0.020 (3)
C2	0.311 (2)	0.325 (3)	0.3549 (15)	0.021 (3)
H2	0.2603	0.3445	0.3819	0.026*
C3	0.327 (2)	0.213 (3)	0.3255 (13)	0.021 (3)
H3	0.2893	0.1459	0.3310	0.025*
C4	0.411 (2)	0.225 (3)	0.2865 (14)	0.020 (3)
H4	0.4364	0.1679	0.2604	0.024*
C5	0.446 (2)	0.336 (3)	0.2944 (14)	0.021 (3)
H5	0.5021	0.3659	0.2751	0.025*
C6	0.262 (2)	0.481 (3)	0.2173 (14)	0.022 (3)
H6	0.2804	0.5571	0.2283	0.027*
C7	0.184 (2)	0.431 (3)	0.2378 (15)	0.022 (3)
H7	0.1366	0.4635	0.2638	0.027*
C8	0.183 (2)	0.315 (3)	0.2129 (15)	0.022 (3)
H8	0.1371	0.2565	0.2202	0.026*
C9	0.270 (2)	0.307 (3)	0.1744 (15)	0.022 (3)
H9	0.2884	0.2416	0.1515	0.026*
C10	0.319 (2)	0.410 (3)	0.1767 (15)	0.022 (3)
H10	0.3766	0.4302	0.1561	0.027*
C11	0.400 (2)	0.514 (3)	0.3554 (17)	0.024 (4)
C12	0.413 (2)	0.610 (3)	0.3764 (17)	0.024 (4)
C13	0.416 (2)	0.996 (3)	0.5049 (14)	0.021 (4)
H13A	0.3919	0.9354	0.5328	0.025*
H13B	0.4513	1.0532	0.5297	0.025*
C14	0.328 (2)	1.056 (3)	0.4723 (16)	0.023 (6)
H14A	0.3092	1.0108	0.4365	0.034*
H14B	0.3467	1.1333	0.4595	0.034*
H14C	0.2736	1.0606	0.5006	0.034*
C15	0.534 (2)	1.044 (3)	0.3981 (14)	0.018 (4)
H15A	0.5866	1.0147	0.3717	0.021*
H15B	0.4786	1.0619	0.3716	0.021*
C16	0.569 (3)	1.157 (3)	0.4268 (16)	0.026 (6)
H16A	0.5800	1.2136	0.3947	0.040*
H16B	0.6291	1.1429	0.4490	0.040*
H16C	0.5197	1.1852	0.4550	0.040*
C17	0.606 (2)	0.904 (3)	0.4966 (15)	0.021 (4)
H17A	0.6293	0.9785	0.5131	0.025*
H17B	0.5876	0.8552	0.5314	0.025*
C18	0.689 (2)	0.846 (3)	0.4614 (17)	0.026 (6)
H18A	0.7130	0.8983	0.4299	0.039*
H18B	0.6653	0.7754	0.4423	0.039*
H18C	0.7413	0.8273	0.4896	0.039*
Au2	0.58322 (10)	0.20278 (11)	0.09390 (5)	0.0256 (3)
Fe2	0.6901 (3)	0.6280 (4)	0.2405 (2)	0.0188 (9)
P2	0.5757 (6)	0.0362 (8)	0.0423 (4)	0.0224 (16)
C21	0.601 (2)	0.566 (3)	0.1724 (14)	0.022 (3)
C22	0.548 (2)	0.622 (3)	0.2205 (14)	0.022 (3)
H22	0.4992	0.5877	0.2447	0.026*
C23	0.580 (2)	0.739 (3)	0.2256 (15)	0.023 (3)
H23	0.5558	0.7961	0.2527	0.027*
C24	0.654 (2)	0.753 (3)	0.1827 (14)	0.024 (3)
H24	0.6919	0.8251	0.1771	0.029*
C25	0.669 (2)	0.655 (3)	0.1501 (15)	0.023 (3)
H25	0.7149	0.6456	0.1185	0.027*
C26	0.754 (3)	0.484 (3)	0.2807 (15)	0.025 (3)
H26	0.7426	0.4054	0.2723	0.030*
C27	0.707 (3)	0.557 (3)	0.3255 (16)	0.026 (3)
H27	0.6578	0.5339	0.3527	0.032*
C28	0.749 (3)	0.673 (3)	0.3220 (15)	0.026 (3)
H28	0.7305	0.7380	0.3455	0.031*
C29	0.823 (3)	0.668 (3)	0.2755 (15)	0.025 (3)
H29	0.8644	0.7295	0.2644	0.030*
C30	0.823 (2)	0.565 (3)	0.2512 (15)	0.025 (3)
H30	0.8651	0.5424	0.2163	0.030*
C31	0.595 (2)	0.449 (3)	0.1542 (13)	0.018 (4)
C32	0.590 (2)	0.353 (3)	0.1352 (12)	0.017 (4)
C33	0.479 (3)	−0.057 (3)	0.0699 (17)	0.029 (5)
H33A	0.4676	−0.1178	0.0392	0.035*
H33B	0.5011	−0.0951	0.1077	0.035*
C34	0.387 (3)	0.001 (4)	0.083 (2)	0.043 (10)
H34A	0.3646	0.0414	0.0458	0.065*
H34B	0.3954	0.0571	0.1155	0.065*
H34C	0.3382	−0.0555	0.0946	0.065*
C35	0.686 (3)	−0.047 (3)	0.0405 (16)	0.026 (4)
H35A	0.7374	−0.0008	0.0210	0.031*
H35B	0.7068	−0.0630	0.0829	0.031*
C36	0.678 (3)	−0.157 (4)	0.008 (2)	0.041 (9)
H36A	0.7325	−0.2065	0.0179	0.062*
H36B	0.6767	−0.1428	−0.0362	0.062*
H36C	0.6175	−0.1955	0.0197	0.062*
C37	0.539 (3)	0.057 (3)	−0.0382 (14)	0.025 (4)
H37A	0.5332	−0.0189	−0.0584	0.030*
H37B	0.4757	0.0953	−0.0399	0.030*
C38	0.614 (3)	0.130 (4)	−0.0718 (17)	0.036 (8)
H38A	0.5851	0.1633	−0.1084	0.053*
H38B	0.6691	0.0814	−0.0836	0.053*
H38C	0.6369	0.1914	−0.0450	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.0125 (4)	0.0207 (6)	0.0189 (5)	0.0017 (5)	−0.0032 (4)	−0.0032 (7)
Fe1	0.0191 (18)	0.014 (2)	0.0180 (19)	−0.0001 (15)	−0.0018 (15)	−0.0009 (17)
P1	0.014 (3)	0.016 (3)	0.016 (3)	−0.002 (2)	0.000 (2)	−0.002 (2)
C1	0.021 (5)	0.020 (4)	0.020 (5)	−0.001 (3)	−0.004 (4)	0.000 (3)
C2	0.022 (6)	0.021 (5)	0.021 (4)	−0.002 (4)	−0.003 (4)	0.000 (3)
C3	0.021 (6)	0.019 (5)	0.022 (5)	−0.001 (4)	−0.004 (4)	0.001 (4)
C4	0.020 (5)	0.018 (5)	0.021 (6)	−0.001 (4)	−0.004 (4)	0.001 (4)
C5	0.022 (4)	0.019 (5)	0.021 (5)	−0.001 (3)	−0.003 (4)	0.001 (4)
C6	0.025 (5)	0.019 (5)	0.023 (5)	0.000 (4)	−0.006 (4)	−0.001 (4)
C7	0.024 (5)	0.018 (6)	0.025 (6)	0.001 (4)	−0.006 (4)	−0.001 (4)
C8	0.023 (5)	0.018 (6)	0.024 (6)	0.001 (4)	−0.006 (4)	−0.001 (4)
C9	0.024 (6)	0.019 (6)	0.022 (4)	0.001 (4)	−0.006 (4)	−0.001 (4)
C10	0.026 (6)	0.020 (6)	0.021 (4)	0.000 (4)	−0.005 (4)	0.000 (4)
C11	0.015 (8)	0.022 (4)	0.035 (9)	−0.001 (4)	−0.001 (7)	−0.006 (5)
C12	0.013 (8)	0.022 (4)	0.038 (10)	−0.001 (5)	−0.001 (7)	−0.008 (5)
C13	0.020 (6)	0.020 (9)	0.022 (7)	0.001 (6)	0.003 (5)	−0.003 (6)
C14	0.019 (7)	0.016 (12)	0.033 (12)	−0.002 (8)	0.001 (7)	0.001 (10)
C15	0.015 (9)	0.016 (6)	0.022 (7)	0.000 (5)	0.001 (6)	−0.001 (5)
C16	0.034 (16)	0.017 (7)	0.028 (12)	−0.005 (8)	−0.006 (11)	0.000 (7)
C17	0.018 (5)	0.019 (9)	0.025 (7)	−0.001 (5)	−0.005 (5)	−0.001 (6)
C18	0.021 (7)	0.017 (14)	0.041 (13)	−0.003 (8)	0.000 (7)	−0.005 (11)
Au2	0.0424 (8)	0.0175 (6)	0.0167 (5)	0.0084 (6)	−0.0035 (5)	−0.0039 (7)
Fe2	0.024 (2)	0.017 (2)	0.0160 (19)	−0.0004 (16)	−0.0033 (15)	0.0018 (17)
P2	0.031 (4)	0.015 (3)	0.021 (3)	−0.003 (3)	0.002 (3)	−0.005 (3)
C21	0.028 (5)	0.018 (4)	0.019 (5)	0.001 (4)	−0.005 (4)	0.001 (3)
C22	0.027 (4)	0.019 (5)	0.019 (5)	0.000 (3)	−0.005 (4)	0.001 (4)
C23	0.028 (5)	0.019 (5)	0.022 (6)	0.000 (4)	−0.006 (4)	0.001 (4)
C24	0.029 (6)	0.020 (5)	0.022 (5)	0.000 (4)	−0.006 (4)	0.003 (4)
C25	0.028 (6)	0.020 (5)	0.021 (4)	0.000 (4)	−0.006 (4)	0.003 (3)
C26	0.030 (6)	0.021 (5)	0.024 (6)	0.000 (4)	−0.008 (5)	0.003 (4)
C27	0.033 (6)	0.023 (6)	0.023 (5)	0.001 (4)	−0.008 (4)	0.003 (4)
C28	0.032 (6)	0.023 (6)	0.023 (5)	0.001 (4)	−0.009 (4)	0.002 (4)
C29	0.030 (5)	0.021 (6)	0.025 (6)	0.001 (4)	−0.009 (4)	0.002 (4)
C30	0.029 (5)	0.020 (6)	0.025 (6)	0.001 (4)	−0.007 (4)	0.002 (4)
C31	0.028 (9)	0.017 (4)	0.010 (7)	0.002 (4)	−0.005 (6)	0.003 (4)
C32	0.028 (9)	0.017 (4)	0.008 (7)	0.003 (4)	−0.006 (7)	0.003 (4)
C33	0.038 (7)	0.023 (8)	0.027 (10)	−0.004 (6)	0.004 (6)	−0.004 (7)
C34	0.041 (8)	0.025 (14)	0.06 (3)	−0.002 (8)	0.018 (10)	0.007 (14)
C35	0.036 (6)	0.017 (8)	0.024 (10)	0.002 (5)	0.006 (6)	0.002 (7)
C36	0.052 (15)	0.024 (9)	0.048 (19)	0.005 (9)	0.001 (13)	−0.011 (11)
C37	0.042 (10)	0.013 (10)	0.020 (5)	0.005 (7)	0.003 (5)	−0.005 (5)
C38	0.050 (14)	0.033 (16)	0.024 (9)	−0.005 (13)	0.001 (8)	0.003 (10)

Geometric parameters (Å, º)

Au1—P1	2.278 (8)	Au2—P2	2.248 (9)
Au1—C12	1.98 (3)	Au2—C32	1.97 (3)
Fe1—C1	2.04 (3)	Fe2—C21	2.07 (3)
Fe1—C2	2.05 (3)	Fe2—C22	2.02 (3)
Fe1—C3	2.07 (3)	Fe2—C23	2.03 (3)
Fe1—C4	2.04 (3)	Fe2—C24	1.99 (3)
Fe1—C5	2.03 (3)	Fe2—C25	2.03 (3)
Fe1—C6	1.99 (3)	Fe2—C26	2.09 (3)
Fe1—C7	2.08 (3)	Fe2—C27	2.05 (4)
Fe1—C8	2.07 (3)	Fe2—C28	2.03 (3)
Fe1—C9	2.04 (3)	Fe2—C29	2.05 (3)
Fe1—C10	2.04 (3)	Fe2—C30	2.00 (3)
P1—C13	1.83 (3)	P2—C33	1.83 (4)
P1—C15	1.81 (3)	P2—C35	1.82 (4)
P1—C17	1.82 (3)	P2—C37	1.86 (3)
C1—C2	1.41 (5)	C21—C22	1.45 (5)
C1—C5	1.43 (5)	C21—C25	1.48 (5)
C1—C11	1.42 (5)	C21—C31	1.43 (5)
C2—C3	1.47 (5)	C22—C23	1.44 (5)
C3—C4	1.45 (4)	C23—C24	1.40 (5)
C4—C5	1.39 (4)	C24—C25	1.36 (5)
C6—C7	1.32 (5)	C26—C27	1.45 (5)
C6—C10	1.44 (5)	C26—C30	1.49 (5)
C7—C8	1.45 (5)	C27—C28	1.47 (5)
C8—C9	1.47 (5)	C28—C29	1.45 (5)
C9—C10	1.38 (5)	C29—C30	1.32 (5)
C11—C12	1.22 (5)	C31—C32	1.19 (5)
C13—C14	1.58 (4)	C33—C34	1.48 (5)
C15—C16	1.53 (4)	C35—C36	1.47 (5)
C17—C18	1.55 (4)	C37—C38	1.53 (5)
C12—Au1—P1	170.8 (11)	C32—Au2—P2	177.1 (9)
C1—Fe1—C2	40.3 (13)	C21—Fe2—C26	106.2 (13)
C1—Fe1—C3	68.7 (13)	C22—Fe2—C21	41.4 (13)
C1—Fe1—C7	118.9 (13)	C22—Fe2—C23	41.5 (13)
C1—Fe1—C8	154.3 (13)	C22—Fe2—C25	69.6 (13)
C1—Fe1—C9	161.7 (13)	C22—Fe2—C26	118.6 (14)
C2—Fe1—C3	41.8 (13)	C22—Fe2—C27	107.4 (14)
C2—Fe1—C7	108.5 (13)	C22—Fe2—C28	126.1 (14)
C2—Fe1—C8	121.0 (13)	C22—Fe2—C29	164.8 (14)
C3—Fe1—C7	129.0 (13)	C23—Fe2—C21	69.9 (13)
C3—Fe1—C8	109.6 (13)	C23—Fe2—C25	68.5 (13)
C4—Fe1—C1	69.0 (13)	C23—Fe2—C26	153.9 (14)
C4—Fe1—C2	70.0 (13)	C23—Fe2—C27	119.3 (14)
C4—Fe1—C3	41.2 (12)	C23—Fe2—C28	106.1 (14)
C4—Fe1—C7	166.7 (13)	C23—Fe2—C29	126.2 (14)
C4—Fe1—C8	127.7 (13)	C24—Fe2—C21	69.1 (14)
C4—Fe1—C9	107.2 (13)	C24—Fe2—C22	68.9 (13)
C5—Fe1—C1	41.0 (13)	C24—Fe2—C23	40.9 (13)
C5—Fe1—C2	68.5 (13)	C24—Fe2—C25	39.4 (14)
C5—Fe1—C3	67.9 (13)	C24—Fe2—C26	163.7 (14)
C5—Fe1—C4	40.0 (12)	C24—Fe2—C27	154.2 (15)
C5—Fe1—C7	152.7 (14)	C24—Fe2—C28	118.2 (14)
C5—Fe1—C8	164.1 (14)	C24—Fe2—C29	107.3 (14)
C5—Fe1—C9	124.9 (13)	C24—Fe2—C30	125.1 (14)
C5—Fe1—C10	106.0 (13)	C25—Fe2—C21	42.4 (13)
C6—Fe1—C1	107.6 (13)	C25—Fe2—C26	126.8 (14)
C6—Fe1—C2	125.2 (14)	C25—Fe2—C27	165.3 (15)
C6—Fe1—C3	163.7 (13)	C25—Fe2—C28	151.3 (14)
C6—Fe1—C4	153.8 (13)	C25—Fe2—C29	117.4 (14)
C6—Fe1—C5	120.5 (14)	C27—Fe2—C21	126.0 (14)
C6—Fe1—C7	37.7 (13)	C27—Fe2—C26	41.0 (14)
C6—Fe1—C8	66.4 (13)	C28—Fe2—C21	164.6 (14)
C6—Fe1—C9	67.3 (13)	C28—Fe2—C26	70.5 (14)
C6—Fe1—C10	42.0 (14)	C28—Fe2—C27	42.0 (15)
C8—Fe1—C7	41.0 (13)	C28—Fe2—C29	41.6 (14)
C9—Fe1—C2	156.9 (13)	C29—Fe2—C21	152.5 (14)
C9—Fe1—C3	121.1 (14)	C29—Fe2—C26	69.2 (14)
C9—Fe1—C7	68.7 (13)	C29—Fe2—C27	69.3 (14)
C9—Fe1—C8	41.7 (13)	C30—Fe2—C21	120.4 (14)
C10—Fe1—C1	124.8 (14)	C30—Fe2—C22	156.0 (14)
C10—Fe1—C2	162.5 (14)	C30—Fe2—C23	161.5 (14)
C10—Fe1—C3	153.2 (14)	C30—Fe2—C25	107.8 (14)
C10—Fe1—C4	117.1 (13)	C30—Fe2—C26	42.7 (14)
C10—Fe1—C7	68.4 (14)	C30—Fe2—C27	68.8 (14)
C10—Fe1—C8	68.8 (13)	C30—Fe2—C28	67.9 (15)
C10—Fe1—C9	39.6 (13)	C30—Fe2—C29	38.0 (14)
C13—P1—Au1	115.7 (11)	C33—P2—Au2	112.3 (12)
C15—P1—Au1	115.1 (10)	C33—P2—C37	101.1 (17)
C15—P1—C13	106.5 (15)	C35—P2—Au2	115.7 (12)
C15—P1—C17	105.0 (15)	C35—P2—C33	108.0 (17)
C17—P1—Au1	111.0 (11)	C35—P2—C37	106.2 (16)
C17—P1—C13	102.3 (16)	C37—P2—Au2	112.5 (11)
C2—C1—Fe1	70.1 (18)	C22—C21—Fe2	67.7 (18)
C2—C1—C5	108 (3)	C22—C21—C25	104 (3)
C2—C1—C11	125 (3)	C25—C21—Fe2	67.5 (18)
C5—C1—Fe1	69.1 (18)	C31—C21—Fe2	125 (2)
C11—C1—Fe1	128 (2)	C31—C21—C22	127 (3)
C11—C1—C5	127 (3)	C31—C21—C25	128 (3)
C1—C2—Fe1	69.5 (19)	C21—C22—Fe2	70.9 (19)
C1—C2—C3	107 (3)	C23—C22—Fe2	69.5 (18)
C3—C2—Fe1	69.8 (17)	C23—C22—C21	109 (3)
C2—C3—Fe1	68.4 (18)	C22—C23—Fe2	69.0 (18)
C4—C3—Fe1	68.2 (18)	C24—C23—Fe2	68.2 (19)
C4—C3—C2	107 (3)	C24—C23—C22	106 (3)
C3—C4—Fe1	70.6 (18)	C23—C24—Fe2	70.9 (19)
C5—C4—Fe1	69.7 (18)	C25—C24—Fe2	72 (2)
C5—C4—C3	107 (3)	C25—C24—C23	112 (3)
C1—C5—Fe1	69.9 (18)	C21—C25—Fe2	70.1 (18)
C4—C5—Fe1	70.3 (17)	C24—C25—Fe2	68.8 (19)
C4—C5—C1	110 (3)	C24—C25—C21	108 (3)
C7—C6—Fe1	75 (2)	C27—C26—Fe2	68.3 (19)
C7—C6—C10	114 (3)	C27—C26—C30	102 (3)
C10—C6—Fe1	70.6 (19)	C30—C26—Fe2	65.4 (18)
C6—C7—Fe1	67 (2)	C26—C27—Fe2	70.7 (19)
C6—C7—C8	107 (3)	C26—C27—C28	109 (3)
C8—C7—Fe1	69.2 (18)	C28—C27—Fe2	68 (2)
C7—C8—Fe1	69.8 (18)	C27—C28—Fe2	69.7 (19)
C7—C8—C9	106 (3)	C29—C28—Fe2	69.7 (19)
C9—C8—Fe1	68.1 (17)	C29—C28—C27	106 (3)
C8—C9—Fe1	70.2 (18)	C28—C29—Fe2	68.7 (19)
C10—C9—Fe1	69.9 (19)	C30—C29—Fe2	69 (2)
C10—C9—C8	109 (3)	C30—C29—C28	109 (3)
C6—C10—Fe1	67.3 (18)	C26—C30—Fe2	71.9 (19)
C9—C10—Fe1	70 (2)	C29—C30—Fe2	73 (2)
C9—C10—C6	105 (3)	C29—C30—C26	113 (3)
C12—C11—C1	176 (4)	C32—C31—C21	176 (3)
C11—C12—Au1	174 (3)	C31—C32—Au2	173 (3)
C14—C13—P1	112 (2)	C34—C33—P2	115 (3)
C16—C15—P1	117 (2)	C36—C35—P2	114 (3)
C18—C17—P1	114 (2)	C38—C37—P2	110 (3)

(1-200k)

Crystal data

C18H24AuFeP	Dx = 1.954 Mg m^−3
Mr = 524.16	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9928 reflections
a = 14.0011 (19) Å	θ = 2.5–28.2°
b = 11.6244 (16) Å	µ = 9.12 mm^−1
c = 21.893 (3) Å	T = 200 K
V = 3563.3 (8) Å^3	Block, clear reddish brown
Z = 8	0.21 × 0.17 × 0.12 mm
F(000) = 2016

Data collection

Bruker APEX-II CCD diffractometer	5048 independent reflections
Radiation source: rotating anode X-ray tube, Bruker TXS	3964 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.041
Detector resolution: 7.9 pixels mm^-1	θmax = 29.8°, θmin = 1.9°
φ and ω scans	h = −19→18
Absorption correction: multi-scan SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1149 before and 0.0801 after correction. The Ratio of minimum to maximum transmission is 0.5166. The λ/2 correction factor is 0.0015.	k = −11→16
Tmin = 0.285, Tmax = 0.552	l = −30→30
27588 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.022	H-atom parameters constrained
wR(F^2) = 0.047	w = 1/[σ^2(Fo^2) + (0.016P)^2 + 1.8511P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
5048 reflections	Δρmax = 0.74 e Å^−3
193 parameters	Δρmin = −0.71 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Au1	0.44772 (2)	0.29652 (2)	0.34609 (2)	0.02543 (4)
Fe1	0.30636 (3)	−0.12974 (3)	0.48724 (2)	0.02303 (9)
P1	0.49872 (5)	0.46111 (6)	0.29991 (3)	0.02197 (15)
C1	0.39035 (19)	−0.0717 (2)	0.41695 (12)	0.0244 (6)
C2	0.4462 (2)	−0.1338 (3)	0.46101 (14)	0.0288 (6)
H2	0.4991	−0.1044	0.4832	0.035*
C3	0.4082 (2)	−0.2472 (3)	0.46552 (15)	0.0308 (7)
H3	0.4316	−0.3065	0.4914	0.037*
C4	0.3298 (2)	−0.2566 (3)	0.42502 (14)	0.0306 (7)
H4	0.2917	−0.3232	0.4189	0.037*
C5	0.3183 (2)	−0.1495 (3)	0.39526 (13)	0.0274 (6)
H5	0.2707	−0.1320	0.3658	0.033*
C6	0.2508 (3)	0.0097 (3)	0.53059 (16)	0.0456 (9)
H6	0.2648	0.0880	0.5220	0.055*
C7	0.3003 (3)	−0.0613 (3)	0.57240 (15)	0.0503 (10)
H7	0.3535	−0.0398	0.5968	0.060*
C8	0.2551 (3)	−0.1715 (3)	0.57107 (15)	0.0445 (9)
H8	0.2728	−0.2367	0.5947	0.053*
C9	0.1804 (2)	−0.1664 (3)	0.52899 (16)	0.0425 (9)
H9	0.1387	−0.2280	0.5190	0.051*
C10	0.1771 (2)	−0.0554 (3)	0.50383 (17)	0.0456 (9)
H10	0.1330	−0.0290	0.4740	0.055*
C11	0.4033 (2)	0.0452 (3)	0.39855 (13)	0.0277 (6)
C12	0.4154 (2)	0.1433 (3)	0.38151 (14)	0.0300 (7)
C13	0.4167 (2)	0.5266 (3)	0.24534 (13)	0.0294 (7)
H13A	0.4515	0.5853	0.2213	0.035*
H13B	0.3940	0.4668	0.2166	0.035*
C14	0.3307 (2)	0.5830 (3)	0.27576 (16)	0.0379 (8)
H14A	0.2865	0.6107	0.2443	0.057*
H14B	0.3522	0.6478	0.3008	0.057*
H14C	0.2981	0.5265	0.3017	0.057*
C15	0.5316 (2)	0.5757 (3)	0.35231 (13)	0.0290 (7)
H15A	0.4750	0.5947	0.3776	0.035*
H15B	0.5816	0.5461	0.3802	0.035*
C16	0.5681 (2)	0.6865 (3)	0.32326 (16)	0.0358 (7)
H16A	0.5213	0.7146	0.2935	0.054*
H16B	0.6289	0.6715	0.3025	0.054*
H16C	0.5777	0.7448	0.3550	0.054*
C17	0.60457 (19)	0.4319 (3)	0.25423 (13)	0.0261 (6)
H17A	0.5868	0.3809	0.2198	0.031*
H17B	0.6283	0.5051	0.2368	0.031*
C18	0.6850 (2)	0.3753 (3)	0.29070 (15)	0.0366 (7)
H18A	0.7384	0.3575	0.2633	0.055*
H18B	0.6614	0.3041	0.3094	0.055*
H18C	0.7067	0.4280	0.3228	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.02969 (6)	0.02138 (6)	0.02522 (6)	−0.00376 (5)	0.00615 (4)	0.00319 (5)
Fe1	0.0305 (2)	0.0175 (2)	0.02112 (18)	0.00110 (16)	0.00578 (16)	0.00179 (17)
P1	0.0239 (4)	0.0209 (4)	0.0211 (3)	−0.0034 (3)	0.0012 (3)	0.0023 (3)
C1	0.0269 (15)	0.0226 (15)	0.0238 (14)	−0.0033 (12)	0.0086 (11)	0.0006 (12)
C2	0.0272 (14)	0.0256 (16)	0.0337 (15)	−0.0017 (12)	−0.0005 (13)	−0.0031 (13)
C3	0.0357 (16)	0.0198 (15)	0.0368 (16)	0.0057 (13)	0.0068 (14)	0.0019 (14)
C4	0.0379 (17)	0.0218 (15)	0.0322 (15)	−0.0065 (13)	0.0089 (13)	−0.0073 (13)
C5	0.0327 (16)	0.0293 (16)	0.0203 (13)	−0.0037 (13)	0.0038 (11)	−0.0021 (13)
C6	0.074 (3)	0.0234 (17)	0.0397 (19)	0.0080 (17)	0.0240 (18)	−0.0022 (16)
C7	0.063 (2)	0.062 (3)	0.0256 (17)	0.000 (2)	0.0075 (16)	−0.0153 (18)
C8	0.067 (2)	0.040 (2)	0.0264 (16)	0.0100 (18)	0.0183 (17)	0.0112 (15)
C9	0.044 (2)	0.0344 (19)	0.049 (2)	0.0005 (15)	0.0258 (17)	0.0038 (16)
C10	0.052 (2)	0.039 (2)	0.046 (2)	0.0185 (17)	0.0174 (17)	0.0047 (18)
C11	0.0284 (15)	0.0297 (17)	0.0249 (14)	−0.0029 (13)	0.0063 (12)	0.0021 (13)
C12	0.0317 (15)	0.0300 (17)	0.0282 (15)	−0.0038 (13)	0.0039 (12)	0.0019 (14)
C13	0.0267 (15)	0.0326 (17)	0.0289 (15)	−0.0063 (13)	−0.0040 (12)	0.0069 (14)
C14	0.0254 (15)	0.0328 (18)	0.056 (2)	−0.0006 (13)	−0.0064 (15)	0.0028 (16)
C15	0.0390 (17)	0.0229 (15)	0.0252 (14)	−0.0031 (13)	−0.0012 (12)	−0.0024 (13)
C16	0.0436 (19)	0.0223 (16)	0.0413 (18)	−0.0066 (13)	−0.0122 (15)	0.0013 (14)
C17	0.0255 (15)	0.0260 (15)	0.0267 (14)	−0.0029 (12)	0.0044 (11)	0.0004 (13)
C18	0.0325 (16)	0.0335 (18)	0.0438 (18)	0.0016 (14)	0.0024 (14)	0.0073 (16)

Geometric parameters (Å, º)

Au1—P1	2.2788 (7)	C1—C2	1.436 (4)
Au1—C12	1.994 (3)	C1—C5	1.436 (4)
Fe1—C1	2.051 (3)	C1—C11	1.429 (4)
Fe1—C2	2.041 (3)	C2—C3	1.425 (4)
Fe1—C3	2.031 (3)	C3—C4	1.415 (4)
Fe1—C4	2.034 (3)	C4—C5	1.415 (4)
Fe1—C5	2.034 (3)	C6—C7	1.414 (5)
Fe1—C6	2.033 (3)	C6—C10	1.407 (5)
Fe1—C7	2.029 (3)	C7—C8	1.429 (5)
Fe1—C8	2.030 (3)	C8—C9	1.395 (5)
Fe1—C9	2.031 (3)	C9—C10	1.404 (5)
Fe1—C10	2.038 (3)	C11—C12	1.212 (4)
P1—C13	1.824 (3)	C13—C14	1.524 (4)
P1—C15	1.817 (3)	C15—C16	1.525 (4)
P1—C17	1.820 (3)	C17—C18	1.529 (4)
C12—Au1—P1	173.38 (9)	C10—Fe1—C2	155.74 (14)
C2—Fe1—C1	41.09 (11)	C13—P1—Au1	116.35 (10)
C3—Fe1—C1	69.07 (12)	C15—P1—Au1	114.50 (10)
C3—Fe1—C2	40.98 (12)	C15—P1—C13	105.48 (15)
C3—Fe1—C4	40.74 (12)	C15—P1—C17	106.11 (14)
C3—Fe1—C5	68.57 (12)	C17—P1—Au1	110.02 (10)
C3—Fe1—C6	156.08 (15)	C17—P1—C13	103.34 (13)
C3—Fe1—C9	125.01 (13)	C2—C1—Fe1	69.07 (16)
C3—Fe1—C10	161.87 (14)	C2—C1—C5	106.8 (2)
C4—Fe1—C1	69.11 (12)	C5—C1—Fe1	68.78 (15)
C4—Fe1—C2	68.90 (12)	C11—C1—Fe1	126.7 (2)
C4—Fe1—C10	124.77 (14)	C11—C1—C2	126.7 (3)
C5—Fe1—C1	41.17 (11)	C11—C1—C5	126.5 (3)
C5—Fe1—C2	68.91 (12)	C1—C2—Fe1	69.83 (15)
C5—Fe1—C4	40.70 (12)	C3—C2—Fe1	69.14 (16)
C5—Fe1—C10	107.29 (14)	C3—C2—C1	107.9 (3)
C6—Fe1—C1	107.90 (13)	C2—C3—Fe1	69.88 (17)
C6—Fe1—C2	121.12 (14)	C4—C3—Fe1	69.77 (17)
C6—Fe1—C4	162.24 (15)	C4—C3—C2	108.5 (3)
C6—Fe1—C5	125.71 (13)	C3—C4—Fe1	69.49 (17)
C6—Fe1—C10	40.44 (14)	C5—C4—Fe1	69.63 (16)
C7—Fe1—C1	125.78 (14)	C5—C4—C3	108.0 (3)
C7—Fe1—C2	107.92 (14)	C1—C5—Fe1	70.06 (15)
C7—Fe1—C3	120.54 (15)	C4—C5—Fe1	69.68 (17)
C7—Fe1—C4	155.00 (15)	C4—C5—C1	108.7 (3)
C7—Fe1—C5	163.29 (15)	C7—C6—Fe1	69.45 (19)
C7—Fe1—C6	40.75 (14)	C10—C6—Fe1	69.95 (19)
C7—Fe1—C8	41.23 (14)	C10—C6—C7	108.3 (3)
C7—Fe1—C9	68.43 (16)	C6—C7—Fe1	69.80 (19)
C7—Fe1—C10	68.46 (15)	C6—C7—C8	107.1 (3)
C8—Fe1—C1	163.73 (14)	C8—C7—Fe1	69.42 (19)
C8—Fe1—C2	126.02 (14)	C7—C8—Fe1	69.36 (18)
C8—Fe1—C3	107.41 (14)	C9—C8—Fe1	69.98 (18)
C8—Fe1—C4	119.29 (14)	C9—C8—C7	107.9 (3)
C8—Fe1—C5	153.82 (14)	C8—C9—Fe1	69.85 (19)
C8—Fe1—C6	68.49 (14)	C8—C9—C10	108.8 (3)
C8—Fe1—C9	40.17 (15)	C10—C9—Fe1	70.07 (18)
C8—Fe1—C10	68.06 (15)	C6—C10—Fe1	69.61 (19)
C9—Fe1—C1	154.75 (13)	C9—C10—Fe1	69.57 (18)
C9—Fe1—C2	162.64 (13)	C9—C10—C6	107.9 (3)
C9—Fe1—C4	106.82 (14)	C12—C11—C1	178.2 (3)
C9—Fe1—C5	119.54 (14)	C11—C12—Au1	172.6 (3)
C9—Fe1—C6	67.98 (14)	C14—C13—P1	113.0 (2)
C9—Fe1—C10	40.37 (13)	C16—C15—P1	116.2 (2)
C10—Fe1—C1	120.23 (13)	C18—C17—P1	113.1 (2)