Hexa­carbonyl­[μ₂-η³-N-(3-thienyl­methylidene)-4-(tri­methyl­silyl)­aniline]­diiron

The title compound, [Fe₂(C₁₄H₁₇NSSi)(CO)₆], was produced by the reaction of N-(3-thienyl­methyl­idene)-4-(tri­methyl­silyl)­aniline and Fe₂(CO)₉ via a reaction sequence involving a C—H activation step, followed by an intramolecular hydrogen transfer to the former imine C atom. The crystal structure analysis clearly proves that the reaction takes place regioselectively at the 2-position of the thio­phene moiety. The structure of the title compound consists of an aza­ferra­cyclo­penta­diene ring to which another Fe(CO)₃ moiety is apically coordinated. There are two independent mol­ecules per asymmetric unit, which differ slightly in their bond lengths and angles.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.038
• wR factor = 0.108
• Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      23.26 Deg.

Alert level B
THETM01_ALERT_3_B  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5556
PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6].....      23.26 Deg.

Alert level C
ABSTM02_ALERT_3_C  The ratio of Tmax/Tmin expected RT(exp) is > 1.10
            Absorption corrections should be applied.
            Tmin and Tmax expected:      0.626     0.702
            RT(exp) =      1.121
PLAT057_ALERT_3_C Correction for Absorption Required   RT(exp) ...       1.12
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe3    -   C35     ..       6.65 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C28
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        Si1
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        Si2
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12A   ..  O1      ..       2.80 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H33B   ..  O4      ..       2.78 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H33A   ..  O7      ..       2.74 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H25B   ..  O9      ..       2.77 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H34C   ..  O11     ..       2.77 Ang.
PLAT726_ALERT_1_C H...A   Calc     2.78960, Rep     2.80000 Dev...       0.01 Ang.
              H12A -O1      1.555   2.645
PLAT728_ALERT_1_C D-H..A  Calc      152.24, Rep      151.00 Dev...       1.24 Deg.
              C12  -H12A -O1      1.555   1.555   2.645
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      37.24 Deg.
              C4   -C3   -FE2     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      37.00 Deg.
              C24  -C23  -FE4     1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C20 H17 Fe2 N O6 S Si

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  16 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: XP.

Hexacarbonyl[µ₂-η³-N-(3-thienylmethylidene)-4- (trimethylsilyl)aniline]diiron

Crystal data

[Fe2(C14H17NSSi)(CO)6]	F(000) = 2192
Mr = 539.20	Dx = 1.526 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5103 reflections
a = 25.4591 (11) Å	θ = 3.4–23.4°
b = 14.1058 (7) Å	µ = 1.41 mm^−1
c = 13.2386 (6) Å	T = 293 K
β = 99.223 (3)°	Block, red
V = 4692.8 (4) Å^3	0.34 × 0.30 × 0.25 mm
Z = 8

Data collection

Nonius KappaCCD area-detector diffractometer	5103 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 23.3°, θmin = 3.4°
ω scans	h = −28→27
6680 measured reflections	k = −15→0
6680 independent reflections	l = 0→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0453P)^2 + 0.7589P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.006
6680 reflections	Δρmax = 0.29 e Å^−3
566 parameters	Δρmin = −0.28 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0046 (4)

Special details

Experimental. Spectroscopic data, for (3): ¹H NMR (CDCl₃): 0.28 (s, 9H), 7.18–7.55 (m, 5H), 7.69 (d, 1H), 7.78 (d, 1H), 8.42 (s, 1H); for (4): ¹H NMR (CDCl₃): 0.23 (s, 9H), 4.26 (s, 2H), 6.94–7.88 (m, 7H); MS (EI): 539 (M⁺), 511 (M⁺ - CO), 483 (M⁺ - 2 CO), 455 (M⁺ - 3 CO), 427 (M⁺ - 4 CO), 399 (M⁺ - 5 CO), 371 (M⁺ - 6 CO), 186 (C₁₁H₈NS⁺), 112 (Fe₂⁺), 56 (Fe⁺), 28 (CO⁺).

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 on F² for ALL reflections except for 16 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating R-factor(obs.) and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Fe1	0.42391 (2)	0.14905 (3)	0.21700 (4)	0.04550 (17)
Fe2	0.35204 (2)	0.16274 (3)	0.07024 (4)	0.04668 (17)
S1	0.44194 (5)	0.33918 (7)	0.06043 (9)	0.0659 (3)
C1	0.50626 (17)	0.3043 (4)	0.0572 (3)	0.0770 (13)
H1	0.5336	0.3466	0.0512	0.080*
C2	0.51331 (16)	0.2097 (3)	0.0641 (3)	0.0693 (12)
H2	0.5457	0.1793	0.0632	0.080*
C3	0.46474 (14)	0.1619 (3)	0.0728 (3)	0.0508 (9)
C4	0.42069 (14)	0.2228 (2)	0.0724 (3)	0.0485 (9)
C5	0.44978 (14)	0.0598 (3)	0.0569 (3)	0.0543 (9)
H5A	0.4412	0.0442	−0.0153	0.080*
H5B	0.4778	0.0180	0.0893	0.080*
N1	0.40204 (10)	0.05537 (19)	0.1082 (2)	0.0437 (7)
C6	0.38443 (14)	−0.0417 (2)	0.1146 (3)	0.0478 (8)
C7	0.3569 (2)	−0.0844 (3)	0.0269 (3)	0.0733 (13)
H7	0.3491	−0.0499	−0.0335	0.080*
C8	0.3412 (2)	−0.1783 (3)	0.0297 (3)	0.0755 (13)
H8	0.3228	−0.2052	−0.0297	0.080*
C9	0.35166 (15)	−0.2339 (3)	0.1169 (3)	0.0533 (9)
C10	0.37830 (18)	−0.1891 (3)	0.2018 (3)	0.0711 (12)
H10	0.3861	−0.2232	0.2624	0.080*
C11	0.39421 (18)	−0.0951 (3)	0.2014 (3)	0.0680 (12)
H11	0.4119	−0.0680	0.2614	0.080*
Si1	0.32964 (5)	−0.36084 (7)	0.11404 (9)	0.0578 (3)
C12	0.35533 (18)	−0.4230 (3)	0.0082 (3)	0.0725 (12)
H12A	0.3935	−0.4255	0.0227	0.080*
H12B	0.3445	−0.3893	−0.0547	0.080*
H12C	0.3413	−0.4862	0.0018	0.080*
C13	0.25602 (19)	−0.3658 (4)	0.0933 (4)	0.0893 (15)
H13A	0.2445	−0.4297	0.0777	0.080*
H13B	0.2420	−0.3251	0.0374	0.080*
H13C	0.2433	−0.3452	0.1542	0.080*
C14	0.3556 (2)	−0.4182 (3)	0.2375 (3)	0.0898 (15)
H14A	0.3938	−0.4183	0.2476	0.080*
H14B	0.3429	−0.4823	0.2370	0.080*
H14C	0.3436	−0.3838	0.2921	0.080*
C15	0.47819 (17)	0.0876 (3)	0.2926 (3)	0.0652 (11)
O1	0.51071 (14)	0.0487 (2)	0.3449 (3)	0.1043 (12)
C16	0.44039 (17)	0.2592 (3)	0.2835 (3)	0.0607 (10)
O2	0.45158 (15)	0.3288 (2)	0.3236 (3)	0.0889 (10)
C17	0.37120 (16)	0.1274 (3)	0.2874 (3)	0.0556 (10)
O3	0.33929 (13)	0.1133 (2)	0.3370 (2)	0.0813 (9)
C18	0.29552 (16)	0.0949 (3)	0.0976 (3)	0.0619 (10)
O4	0.25959 (12)	0.0524 (3)	0.1128 (3)	0.0993 (12)
C19	0.32022 (17)	0.2721 (3)	0.0861 (3)	0.0649 (11)
O5	0.30026 (15)	0.3436 (2)	0.0979 (3)	0.1003 (12)
C20	0.33689 (16)	0.1593 (3)	−0.0661 (4)	0.0610 (10)
O6	0.32874 (15)	0.1604 (2)	−0.1535 (3)	0.0930 (11)
Fe3	0.075344 (19)	0.14899 (3)	−0.19456 (4)	0.04322 (16)
Fe4	0.14615 (2)	0.14966 (3)	−0.30072 (4)	0.04856 (17)
S2	0.06606 (4)	0.34218 (6)	−0.35836 (9)	0.0616 (3)
C21	−0.00065 (17)	0.3196 (3)	−0.3922 (3)	0.0659 (11)
H21	−0.0259	0.3668	−0.4105	0.080*
C22	−0.01290 (16)	0.2270 (3)	−0.3896 (3)	0.0611 (10)
H22	−0.0472	0.2029	−0.4066	0.080*
C23	0.03329 (14)	0.1702 (2)	−0.3577 (3)	0.0482 (9)
C24	0.08098 (14)	0.2218 (2)	−0.3355 (3)	0.0473 (8)
C25	0.04149 (14)	0.0661 (2)	−0.3714 (3)	0.0491 (9)
H25A	0.0116	0.0293	−0.3561	0.080*
H25B	0.0478	0.0514	−0.4401	0.080*
N2	0.09020 (11)	0.05065 (18)	−0.2937 (2)	0.0438 (7)
C26	0.10450 (13)	−0.0483 (2)	−0.2814 (3)	0.0425 (8)
C27	0.09766 (19)	−0.1070 (3)	−0.3649 (3)	0.0736 (13)
H27	0.0821	−0.0835	−0.4283	0.080*
C28	0.11392 (19)	−0.2020 (3)	−0.3557 (3)	0.0762 (14)
H28	0.1082	−0.2404	−0.4135	0.080*
C29	0.13800 (14)	−0.2406 (2)	−0.2646 (3)	0.0482 (9)
C30	0.14318 (16)	−0.1802 (3)	−0.1821 (3)	0.0577 (10)
H30	0.1585	−0.2035	−0.1184	0.080*
C31	0.12658 (15)	−0.0857 (2)	−0.1890 (3)	0.0541 (9)
H31	0.1306	−0.0481	−0.1305	0.080*
Si2	0.16371 (4)	−0.36556 (7)	−0.25717 (9)	0.0544 (3)
C32	0.23678 (18)	−0.3626 (3)	−0.2142 (4)	0.0850 (14)
H32A	0.2496	−0.4259	−0.1997	0.080*
H32B	0.2446	−0.3246	−0.1535	0.080*
H32C	0.2538	−0.3357	−0.2672	0.080*
C33	0.14924 (17)	−0.4204 (3)	−0.3856 (3)	0.0684 (11)
H33A	0.1122	−0.4124	−0.4126	0.080*
H33B	0.1576	−0.4867	−0.3805	0.080*
H33C	0.1704	−0.3903	−0.4303	0.080*
C34	0.1313 (2)	−0.4340 (3)	−0.1640 (4)	0.0893 (15)
H34A	0.0934	−0.4336	−0.1854	0.080*
H34B	0.1397	−0.4055	−0.0975	0.080*
H34C	0.1440	−0.4981	−0.1611	0.080*
C35	0.02291 (16)	0.0882 (3)	−0.1467 (3)	0.0548 (9)
O7	−0.01003 (13)	0.0500 (2)	−0.1136 (3)	0.0848 (9)
C36	0.13094 (16)	0.1360 (2)	−0.0966 (3)	0.0540 (9)
O8	0.16447 (13)	0.1322 (2)	−0.0263 (2)	0.0784 (9)
C37	0.05884 (16)	0.2592 (3)	−0.1396 (3)	0.0557 (10)
O9	0.04692 (14)	0.3286 (2)	−0.1053 (2)	0.0806 (9)
C38	0.20067 (16)	0.0753 (3)	−0.2402 (3)	0.0633 (11)
O10	0.23627 (12)	0.0320 (2)	−0.2031 (3)	0.0914 (10)
C39	0.16060 (17)	0.1379 (3)	−0.4279 (4)	0.0624 (10)
O11	0.16930 (15)	0.1337 (3)	−0.5100 (3)	0.0944 (10)
C40	0.18371 (17)	0.2555 (3)	−0.2660 (4)	0.0690 (12)
O12	0.20615 (16)	0.3229 (3)	−0.2438 (3)	0.1111 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0510 (3)	0.0431 (3)	0.0424 (3)	0.0018 (2)	0.0073 (2)	−0.0009 (2)
Fe2	0.0463 (3)	0.0451 (3)	0.0482 (3)	−0.0002 (2)	0.0063 (2)	0.0012 (2)
S1	0.0804 (7)	0.0501 (6)	0.0639 (7)	−0.0159 (5)	0.0018 (6)	0.0079 (5)
C1	0.069 (3)	0.090 (3)	0.072 (3)	−0.033 (3)	0.009 (2)	0.008 (3)
C2	0.055 (2)	0.085 (3)	0.068 (3)	−0.015 (2)	0.010 (2)	0.005 (2)
C3	0.049 (2)	0.055 (2)	0.049 (2)	−0.0021 (17)	0.0101 (17)	0.0015 (17)
C4	0.059 (2)	0.046 (2)	0.039 (2)	−0.0085 (17)	0.0038 (16)	0.0005 (16)
C5	0.055 (2)	0.056 (2)	0.055 (2)	0.0059 (18)	0.0180 (18)	−0.0040 (18)
N1	0.0497 (16)	0.0394 (16)	0.0443 (16)	−0.0010 (12)	0.0145 (13)	−0.0011 (13)
C6	0.057 (2)	0.043 (2)	0.045 (2)	−0.0023 (16)	0.0118 (17)	−0.0045 (16)
C7	0.124 (4)	0.049 (2)	0.044 (2)	−0.013 (2)	0.002 (2)	0.0009 (18)
C8	0.120 (4)	0.056 (2)	0.045 (2)	−0.023 (3)	−0.002 (2)	−0.003 (2)
C9	0.067 (2)	0.049 (2)	0.046 (2)	−0.0046 (18)	0.0134 (18)	0.0024 (17)
C10	0.102 (3)	0.050 (2)	0.054 (3)	−0.012 (2)	−0.011 (2)	0.011 (2)
C11	0.093 (3)	0.052 (2)	0.051 (2)	−0.013 (2)	−0.015 (2)	0.0065 (19)
Si1	0.0715 (7)	0.0472 (6)	0.0551 (7)	−0.0108 (5)	0.0110 (5)	0.0002 (5)
C12	0.086 (3)	0.060 (3)	0.071 (3)	0.000 (2)	0.011 (2)	−0.007 (2)
C13	0.087 (3)	0.086 (4)	0.098 (4)	−0.021 (3)	0.026 (3)	−0.004 (3)
C14	0.126 (4)	0.066 (3)	0.075 (3)	−0.018 (3)	0.007 (3)	0.014 (2)
C15	0.067 (3)	0.054 (2)	0.070 (3)	0.009 (2)	−0.002 (2)	−0.008 (2)
O1	0.098 (2)	0.088 (2)	0.109 (3)	0.029 (2)	−0.037 (2)	−0.007 (2)
C16	0.076 (3)	0.055 (3)	0.052 (2)	0.002 (2)	0.013 (2)	−0.001 (2)
O2	0.137 (3)	0.0579 (19)	0.072 (2)	−0.0182 (18)	0.019 (2)	−0.0216 (16)
C17	0.064 (2)	0.058 (2)	0.046 (2)	0.0018 (19)	0.010 (2)	0.0023 (18)
O3	0.080 (2)	0.101 (2)	0.067 (2)	−0.0073 (18)	0.0286 (17)	0.0102 (18)
C18	0.052 (2)	0.071 (3)	0.063 (3)	0.001 (2)	0.008 (2)	0.010 (2)
O4	0.0618 (19)	0.111 (3)	0.128 (3)	−0.0139 (19)	0.0250 (19)	0.031 (2)
C19	0.067 (3)	0.060 (3)	0.066 (3)	0.015 (2)	0.005 (2)	0.001 (2)
O5	0.106 (3)	0.077 (2)	0.117 (3)	0.036 (2)	0.015 (2)	−0.001 (2)
C20	0.065 (3)	0.059 (2)	0.059 (3)	−0.0127 (19)	0.009 (2)	0.008 (2)
O6	0.119 (3)	0.103 (3)	0.052 (2)	−0.039 (2)	−0.0011 (19)	0.0068 (17)
Fe3	0.0502 (3)	0.0383 (3)	0.0419 (3)	−0.0012 (2)	0.0096 (2)	−0.0011 (2)
Fe4	0.0499 (3)	0.0432 (3)	0.0546 (3)	−0.0032 (2)	0.0146 (2)	−0.0016 (2)
S2	0.0779 (7)	0.0400 (5)	0.0693 (7)	0.0030 (5)	0.0192 (5)	0.0084 (5)
C21	0.072 (3)	0.054 (2)	0.071 (3)	0.016 (2)	0.009 (2)	0.010 (2)
C22	0.061 (2)	0.053 (2)	0.067 (3)	0.0060 (19)	0.004 (2)	0.002 (2)
C23	0.060 (2)	0.0414 (19)	0.043 (2)	0.0038 (17)	0.0094 (17)	0.0029 (16)
C24	0.058 (2)	0.0381 (18)	0.047 (2)	−0.0009 (16)	0.0144 (17)	−0.0002 (16)
C25	0.055 (2)	0.046 (2)	0.043 (2)	0.0032 (17)	0.0013 (17)	0.0016 (16)
N2	0.0497 (16)	0.0386 (16)	0.0425 (16)	0.0012 (12)	0.0057 (13)	0.0015 (12)
C26	0.0463 (18)	0.0346 (18)	0.047 (2)	−0.0009 (14)	0.0077 (15)	−0.0015 (15)
C27	0.113 (4)	0.051 (2)	0.048 (2)	0.028 (2)	−0.011 (2)	−0.0023 (19)
C28	0.115 (4)	0.050 (2)	0.056 (3)	0.022 (2)	−0.011 (3)	−0.017 (2)
C29	0.052 (2)	0.043 (2)	0.050 (2)	0.0022 (16)	0.0087 (17)	−0.0043 (17)
C30	0.082 (3)	0.046 (2)	0.044 (2)	0.0075 (19)	0.0053 (19)	0.0052 (17)
C31	0.078 (3)	0.042 (2)	0.041 (2)	0.0045 (18)	0.0054 (19)	−0.0051 (16)
Si2	0.0647 (7)	0.0433 (6)	0.0555 (7)	0.0092 (5)	0.0106 (5)	0.0002 (5)
C32	0.076 (3)	0.085 (3)	0.088 (4)	0.016 (2)	−0.005 (3)	−0.001 (3)
C33	0.076 (3)	0.055 (2)	0.074 (3)	0.012 (2)	0.014 (2)	−0.010 (2)
C34	0.123 (4)	0.060 (3)	0.091 (4)	0.019 (3)	0.035 (3)	0.014 (3)
C35	0.067 (2)	0.046 (2)	0.054 (2)	−0.0006 (19)	0.015 (2)	−0.0040 (18)
O7	0.091 (2)	0.074 (2)	0.100 (2)	−0.0246 (17)	0.0464 (19)	−0.0035 (17)
C36	0.063 (2)	0.043 (2)	0.055 (2)	−0.0019 (18)	0.007 (2)	−0.0047 (18)
O8	0.081 (2)	0.080 (2)	0.066 (2)	0.0066 (16)	−0.0111 (17)	−0.0025 (16)
C37	0.070 (3)	0.052 (2)	0.047 (2)	0.0018 (19)	0.0139 (19)	−0.0006 (18)
O9	0.106 (2)	0.0615 (19)	0.077 (2)	0.0133 (17)	0.0232 (18)	−0.0179 (16)
C38	0.051 (2)	0.060 (2)	0.080 (3)	−0.004 (2)	0.013 (2)	−0.004 (2)
O10	0.0580 (18)	0.084 (2)	0.129 (3)	0.0091 (17)	0.0044 (18)	0.009 (2)
C39	0.065 (3)	0.063 (3)	0.062 (3)	0.0039 (19)	0.019 (2)	−0.001 (2)
O11	0.115 (3)	0.105 (3)	0.071 (2)	−0.004 (2)	0.039 (2)	−0.0100 (19)
C40	0.064 (3)	0.067 (3)	0.081 (3)	−0.021 (2)	0.026 (2)	−0.007 (2)
O12	0.115 (3)	0.078 (2)	0.145 (4)	−0.047 (2)	0.032 (3)	−0.021 (2)

Geometric parameters (Å, º)

Fe1—C17	1.779 (4)	Fe3—C35	1.786 (4)
Fe1—C15	1.794 (4)	Fe3—C37	1.795 (4)
Fe1—C16	1.802 (4)	Fe3—N2	1.987 (3)
Fe1—N1	1.968 (3)	Fe3—C24	2.154 (3)
Fe1—C4	2.169 (3)	Fe3—C23	2.271 (4)
Fe1—C3	2.322 (4)	Fe3—Fe4	2.4570 (7)
Fe1—Fe2	2.4538 (7)	Fe3—C25	2.635 (3)
Fe1—C5	2.639 (4)	Fe4—C39	1.788 (5)
Fe2—C19	1.770 (4)	Fe4—C40	1.793 (4)
Fe2—C20	1.785 (5)	Fe4—C38	1.820 (4)
Fe2—C18	1.812 (4)	Fe4—C24	1.938 (4)
Fe2—C4	1.939 (4)	Fe4—N2	2.008 (3)
Fe2—N1	1.991 (3)	Fe4—C36	2.797 (4)
Fe2—C3	2.864 (4)	Fe4—C23	2.866 (4)
S1—C1	1.717 (5)	S2—C21	1.715 (4)
S1—C4	1.743 (3)	S2—C24	1.756 (3)
C1—C2	1.348 (6)	C21—C22	1.345 (5)
C1—H1	0.9300	C21—H21	0.9300
C2—C3	1.429 (5)	C22—C23	1.430 (5)
C2—H2	0.9300	C22—H22	0.9300
C3—C4	1.412 (5)	C23—C24	1.406 (5)
C3—C5	1.497 (5)	C23—C25	1.498 (4)
C5—N1	1.486 (4)	C25—N2	1.495 (4)
C5—H5A	0.9700	C25—H25A	0.9700
C5—H5B	0.9700	C25—H25B	0.9700
N1—C6	1.447 (4)	N2—C26	1.446 (4)
C6—C11	1.363 (5)	C26—C31	1.368 (5)
C6—C7	1.393 (5)	C26—C27	1.369 (5)
C7—C8	1.385 (5)	C27—C28	1.402 (5)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.386 (5)	C28—C29	1.375 (5)
C8—H8	0.9300	C28—H28	0.9300
C9—C10	1.370 (5)	C29—C30	1.374 (5)
C9—Si1	1.875 (4)	C29—Si2	1.878 (3)
C10—C11	1.386 (5)	C30—C31	1.397 (5)
C10—H10	0.9300	C30—H30	0.9300
C11—H11	0.9300	C31—H31	0.9300
Si1—C14	1.849 (4)	Si2—C33	1.850 (4)
Si1—C13	1.852 (5)	Si2—C32	1.856 (4)
Si1—C12	1.858 (4)	Si2—C34	1.860 (5)
C12—H12A	0.9600	C32—H32A	0.9600
C12—H12B	0.9600	C32—H32B	0.9600
C12—H12C	0.9600	C32—H32C	0.9600
C13—H13A	0.9600	C33—H33A	0.9600
C13—H13B	0.9600	C33—H33B	0.9600
C13—H13C	0.9600	C33—H33C	0.9600
C14—H14A	0.9600	C34—H34A	0.9600
C14—H14B	0.9600	C34—H34B	0.9600
C14—H14C	0.9600	C34—H34C	0.9600
C15—O1	1.132 (5)	C35—O7	1.141 (4)
C16—O2	1.131 (5)	C36—O8	1.159 (4)
C17—O3	1.141 (5)	C37—O9	1.140 (4)
C18—O4	1.138 (5)	C38—O10	1.138 (5)
C19—O5	1.151 (5)	C39—O11	1.145 (5)
C20—O6	1.142 (5)	C40—O12	1.123 (5)
Fe3—C36	1.769 (4)
C17—Fe1—C15	101.74 (19)	C37—Fe3—N2	162.56 (14)
C17—Fe1—C16	91.60 (18)	C36—Fe3—C24	121.83 (16)
C15—Fe1—C16	92.62 (18)	C35—Fe3—C24	133.91 (16)
C17—Fe1—N1	96.87 (15)	C37—Fe3—C24	89.44 (15)
C15—Fe1—N1	100.72 (15)	N2—Fe3—C24	73.42 (12)
C16—Fe1—N1	162.37 (15)	C36—Fe3—C23	155.55 (16)
C17—Fe1—C4	128.30 (16)	C35—Fe3—C23	97.79 (16)
C15—Fe1—C4	129.85 (18)	C37—Fe3—C23	99.54 (15)
C16—Fe1—C4	89.45 (15)	N2—Fe3—C23	64.82 (11)
N1—Fe1—C4	73.16 (12)	C24—Fe3—C23	36.92 (13)
C17—Fe1—C3	156.76 (15)	C36—Fe3—Fe4	81.11 (13)
C15—Fe1—C3	95.16 (17)	C35—Fe3—Fe4	149.70 (12)
C16—Fe1—C3	103.55 (16)	C37—Fe3—Fe4	117.99 (13)
N1—Fe1—C3	64.07 (12)	N2—Fe3—Fe4	52.42 (8)
C4—Fe1—C3	36.45 (13)	C24—Fe3—Fe4	49.16 (9)
C17—Fe1—Fe2	84.20 (12)	C23—Fe3—Fe4	74.51 (9)
C15—Fe1—Fe2	152.82 (13)	C36—Fe3—C25	135.60 (14)
C16—Fe1—Fe2	113.88 (13)	C35—Fe3—C25	86.89 (15)
N1—Fe1—Fe2	52.11 (8)	C37—Fe3—C25	132.83 (14)
C4—Fe1—Fe2	49.11 (9)	N2—Fe3—C25	34.24 (10)
C3—Fe1—Fe2	73.64 (9)	C24—Fe3—C25	59.99 (12)
C17—Fe1—C5	130.21 (15)	C23—Fe3—C25	34.56 (11)
C15—Fe1—C5	87.04 (16)	Fe4—Fe3—C25	70.06 (8)
C16—Fe1—C5	137.37 (16)	C39—Fe4—C40	97.9 (2)
N1—Fe1—C5	33.83 (11)	C39—Fe4—C38	95.94 (19)
C4—Fe1—C5	59.94 (13)	C40—Fe4—C38	91.70 (19)
C3—Fe1—C5	34.39 (11)	C39—Fe4—C24	97.05 (17)
Fe2—Fe1—C5	69.63 (8)	C40—Fe4—C24	91.41 (18)
C19—Fe2—C20	96.62 (19)	C38—Fe4—C24	166.10 (17)
C19—Fe2—C18	92.49 (19)	C39—Fe4—N2	103.50 (16)
C20—Fe2—C18	97.92 (18)	C40—Fe4—N2	157.05 (16)
C19—Fe2—C4	92.63 (18)	C38—Fe4—N2	94.33 (14)
C20—Fe2—C4	94.32 (16)	C24—Fe4—N2	77.85 (13)
C18—Fe2—C4	166.10 (16)	C39—Fe4—Fe3	144.97 (14)
C19—Fe2—N1	156.80 (16)	C40—Fe4—Fe3	105.47 (14)
C20—Fe2—N1	105.10 (16)	C38—Fe4—Fe3	108.89 (13)
C18—Fe2—N1	92.50 (15)	C24—Fe4—Fe3	57.25 (10)
C4—Fe2—N1	77.90 (13)	N2—Fe4—Fe3	51.68 (8)
C19—Fe2—Fe1	105.77 (14)	C39—Fe4—C36	169.94 (15)
C20—Fe2—Fe1	144.23 (14)	C40—Fe4—C36	87.75 (16)
C18—Fe2—Fe1	108.38 (13)	C38—Fe4—C36	75.46 (16)
C4—Fe2—Fe1	57.76 (10)	C24—Fe4—C36	91.13 (13)
N1—Fe2—Fe1	51.28 (8)	N2—Fe4—C36	72.45 (11)
C19—Fe2—C3	118.60 (16)	Fe3—Fe4—C36	38.68 (8)
C20—Fe2—C3	93.77 (15)	C39—Fe4—C23	96.35 (15)
C18—Fe2—C3	145.22 (15)	C40—Fe4—C23	117.01 (16)
C4—Fe2—C3	26.16 (13)	C38—Fe4—C23	146.70 (14)
N1—Fe2—C3	52.78 (10)	C24—Fe4—C23	25.88 (12)
Fe1—Fe2—C3	51.07 (8)	N2—Fe4—C23	52.68 (10)
C1—S1—C4	92.5 (2)	Fe3—Fe4—C23	49.79 (7)
C2—C1—S1	113.5 (3)	C36—Fe4—C23	88.45 (11)
C2—C1—H1	123.2	C21—S2—C24	92.49 (18)
S1—C1—H1	123.2	C22—C21—S2	113.4 (3)
C1—C2—C3	111.4 (4)	C22—C21—H21	123.3
C1—C2—H2	124.3	S2—C21—H21	123.3
C3—C2—H2	124.3	C21—C22—C23	111.6 (4)
C4—C3—C2	114.2 (3)	C21—C22—H22	124.2
C4—C3—C5	113.6 (3)	C23—C22—H22	124.2
C2—C3—C5	130.2 (4)	C24—C23—C22	114.4 (3)
C4—C3—Fe1	65.9 (2)	C24—C23—C25	113.6 (3)
C2—C3—Fe1	127.7 (3)	C22—C23—C25	129.6 (3)
C5—C3—Fe1	84.5 (2)	C24—C23—Fe3	67.0 (2)
C4—C3—Fe2	37.24 (17)	C22—C23—Fe3	126.5 (3)
C2—C3—Fe2	151.1 (3)	C25—C23—Fe3	86.1 (2)
C5—C3—Fe2	76.72 (19)	C24—C23—Fe4	37.00 (17)
Fe1—C3—Fe2	55.29 (8)	C22—C23—Fe4	151.3 (3)
C3—C4—S1	108.4 (3)	C25—C23—Fe4	77.26 (19)
C3—C4—Fe2	116.6 (3)	Fe3—C23—Fe4	55.71 (8)
S1—C4—Fe2	134.6 (2)	C23—C24—S2	108.0 (3)
C3—C4—Fe1	77.7 (2)	C23—C24—Fe4	117.1 (3)
S1—C4—Fe1	124.32 (18)	S2—C24—Fe4	134.6 (2)
Fe2—C4—Fe1	73.13 (12)	C23—C24—Fe3	76.1 (2)
N1—C5—C3	100.6 (3)	S2—C24—Fe3	124.60 (18)
N1—C5—Fe1	47.50 (15)	Fe4—C24—Fe3	73.59 (12)
C3—C5—Fe1	61.16 (19)	N2—C25—C23	100.1 (3)
N1—C5—H5A	111.7	N2—C25—Fe3	48.42 (14)
C3—C5—H5A	111.7	C23—C25—Fe3	59.30 (18)
Fe1—C5—H5A	148.5	N2—C25—H25A	111.7
N1—C5—H5B	111.7	C23—C25—H25A	111.7
C3—C5—H5B	111.7	Fe3—C25—H25A	102.0
Fe1—C5—H5B	101.2	N2—C25—H25B	111.7
H5A—C5—H5B	109.4	C23—C25—H25B	111.7
C6—N1—C5	110.5 (3)	Fe3—C25—H25B	148.0
C6—N1—Fe1	130.3 (2)	H25A—C25—H25B	109.5
C5—N1—Fe1	98.7 (2)	C26—N2—C25	112.6 (2)
C6—N1—Fe2	122.9 (2)	C26—N2—Fe3	132.1 (2)
C5—N1—Fe2	112.9 (2)	C25—N2—Fe3	97.34 (19)
Fe1—N1—Fe2	76.61 (10)	C26—N2—Fe4	120.6 (2)
C11—C6—C7	117.6 (3)	C25—N2—Fe4	112.5 (2)
C11—C6—N1	123.8 (3)	Fe3—N2—Fe4	75.90 (9)
C7—C6—N1	118.6 (3)	C31—C26—C27	118.1 (3)
C8—C7—C6	119.9 (4)	C31—C26—N2	122.2 (3)
C8—C7—H7	120.0	C27—C26—N2	119.7 (3)
C6—C7—H7	120.0	C26—C27—C28	120.6 (3)
C9—C8—C7	123.1 (4)	C26—C27—H27	119.7
C9—C8—H8	118.4	C28—C27—H27	119.7
C7—C8—H8	118.4	C29—C28—C27	122.6 (4)
C10—C9—C8	115.1 (4)	C29—C28—H28	118.7
C10—C9—Si1	124.4 (3)	C27—C28—H28	118.7
C8—C9—Si1	120.5 (3)	C28—C29—C30	115.1 (3)
C9—C10—C11	123.0 (4)	C28—C29—Si2	121.3 (3)
C9—C10—H10	118.5	C30—C29—Si2	123.5 (3)
C11—C10—H10	118.5	C29—C30—C31	123.4 (3)
C6—C11—C10	121.2 (4)	C29—C30—H30	118.3
C6—C11—H11	119.4	C31—C30—H30	118.3
C10—C11—H11	119.4	C26—C31—C30	120.2 (3)
C14—Si1—C13	108.9 (2)	C26—C31—H31	119.9
C14—Si1—C12	110.0 (2)	C30—C31—H31	119.9
C13—Si1—C12	109.9 (2)	C33—Si2—C32	109.5 (2)
C14—Si1—C9	109.68 (19)	C33—Si2—C34	110.4 (2)
C13—Si1—C9	109.4 (2)	C32—Si2—C34	109.8 (2)
C12—Si1—C9	109.00 (19)	C33—Si2—C29	109.15 (18)
Si1—C12—H12A	109.5	C32—Si2—C29	108.57 (19)
Si1—C12—H12B	109.5	C34—Si2—C29	109.48 (19)
H12A—C12—H12B	109.5	Si2—C32—H32A	109.5
Si1—C12—H12C	109.5	Si2—C32—H32B	109.5
H12A—C12—H12C	109.5	H32A—C32—H32B	109.5
H12B—C12—H12C	109.5	Si2—C32—H32C	109.5
Si1—C13—H13A	109.5	H32A—C32—H32C	109.5
Si1—C13—H13B	109.5	H32B—C32—H32C	109.5
H13A—C13—H13B	109.5	Si2—C33—H33A	109.5
Si1—C13—H13C	109.5	Si2—C33—H33B	109.5
H13A—C13—H13C	109.5	H33A—C33—H33B	109.5
H13B—C13—H13C	109.5	Si2—C33—H33C	109.5
Si1—C14—H14A	109.5	H33A—C33—H33C	109.5
Si1—C14—H14B	109.5	H33B—C33—H33C	109.5
H14A—C14—H14B	109.5	Si2—C34—H34A	109.5
Si1—C14—H14C	109.5	Si2—C34—H34B	109.5
H14A—C14—H14C	109.5	H34A—C34—H34B	109.5
H14B—C14—H14C	109.5	Si2—C34—H34C	109.5
O1—C15—Fe1	175.9 (4)	H34A—C34—H34C	109.5
O2—C16—Fe1	178.3 (4)	H34B—C34—H34C	109.5
O3—C17—Fe1	176.5 (4)	O7—C35—Fe3	178.3 (4)
O4—C18—Fe2	178.7 (4)	O8—C36—Fe3	173.3 (4)
O5—C19—Fe2	178.8 (4)	O8—C36—Fe4	125.5 (3)
O6—C20—Fe2	176.9 (4)	Fe3—C36—Fe4	60.22 (12)
C36—Fe3—C35	104.23 (18)	O9—C37—Fe3	178.1 (4)
C36—Fe3—C37	90.27 (17)	O10—C38—Fe4	177.0 (4)
C35—Fe3—C37	92.03 (17)	O11—C39—Fe4	177.5 (4)
C36—Fe3—N2	101.36 (14)	O12—C40—Fe4	178.3 (4)
C35—Fe3—N2	97.56 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	H···A	D···A	D—H···A
C12—H12A···O1^i	2.80	3.668 (5)	151
C33—H33B···O4^ii	2.78	3.376 (6)	121
C33—H33A···O7^iii	2.74	3.567 (6)	145
C25—H25B···O9^iv	2.77	3.458 (5)	129
C34—H34C···O11^v	2.77	3.521 (6)	136

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