N-[1′-(2,4,6-Trimethyl­anilino)-1-ferrocen­yl]-N-(2,4,6-trimethyl­phen­yl)thio­carbamoyl chloride

The title compound, [Fe(C₁₅H₁₅ClNS)(C₁₄H₁₆N)], crystallizes with the thio­carbamoyl chloride unit nearly coplanar with the cyclo­penta­dienyl ring to which it is attached. There is a slight deviation from planarity which, along with the orientation of the amino substituent on the other cyclo­penta­dienyl ring, is suggestive of an intra­molecular hydrogen bond. The long donor–acceptor N...S length of 3.702 (2) Å indicates that any inter­action is weak.

Key indicators

• Single-crystal X-ray study
• T = 161 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.043
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT073_ALERT_1_A H-atoms ref, but _hydrogen_treatment reported as     constr

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C20     ..       5.88 su
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C19
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C27
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H31    ...          ?
PLAT704_ALERT_1_C Contact Calc  3.7001(17), Rep    3.702(2), Dev..       1.12 Sigma
              S1   -N2      1.555   1.555

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 1998); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN.

N-[1'-(2,4,6-Trimethylanilino)-1-ferrocenyl]-N-(2,4,6- trimethylphenyl)thiocarbamoyl chloride

Crystal data

[Fe(C15H15ClNS)(C14H16N)]	F(000) = 1112.00
Mr = 530.94	Dx = 1.373 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 5416 reflections
a = 9.6245 (5) Å	θ = 2.4–26.3°
b = 20.623 (1) Å	µ = 0.79 mm^−1
c = 13.6569 (7) Å	T = 161 K
β = 108.699 (1)°	Column, red
V = 2567.7 (2) Å^3	0.20 × 0.12 × 0.05 mm
Z = 4

Data collection

Bruker APEX diffractometer	3992 reflections with F^2 > 3σ(F^2)
ω scans	Rint = 0.019
Absorption correction: ψ scan (SORTAV; Blessing, 1995)	θmax = 26.4°
Tmin = 0.825, Tmax = 0.961	h = 0→12
14858 measured reflections	k = 0→25
5213 independent reflections	l = −17→16

Refinement

Refinement on F	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.033	w = 1/[σ^2(Fo) + 0.00022|Fo|^2]
wR(F^2) = 0.043	(Δ/σ)max = 0.001
S = 1.87	Δρmax = 0.29 e Å^−3
3992 reflections	Δρmin = −0.22 e Å^−3
310 parameters

Special details

Refinement. Refinement using reflections with F² > 3.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F.

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

	x	y	z	Uiso*/Ueq
Fe1	0.19814 (2)	0.28258 (1)	0.29824 (2)	0.03027 (6)
Cl1	−0.07088 (5)	0.27780 (2)	0.59702 (4)	0.0504 (1)
S1	0.17513 (7)	0.34682 (2)	0.56535 (4)	0.0579 (2)
N1	0.0581 (1)	0.23615 (6)	0.46852 (10)	0.0315 (3)
N2	0.3086 (2)	0.42700 (7)	0.3701 (1)	0.0433 (4)
C1	0.1625 (2)	0.22895 (7)	0.4138 (1)	0.0297 (4)
C2	0.1324 (2)	0.19129 (8)	0.3209 (1)	0.0350 (4)
C3	0.2631 (2)	0.18860 (8)	0.2956 (1)	0.0397 (5)
C4	0.3721 (2)	0.22407 (7)	0.3702 (1)	0.0381 (5)
C5	0.3113 (2)	0.24919 (8)	0.4437 (1)	0.0335 (4)
C6	0.2245 (2)	0.38348 (8)	0.2949 (1)	0.0370 (4)
C7	0.0761 (2)	0.36609 (8)	0.2785 (1)	0.0426 (5)
C8	0.0294 (2)	0.32594 (9)	0.1889 (1)	0.0445 (5)
C9	0.1492 (2)	0.31782 (8)	0.1513 (1)	0.0418 (5)
C10	0.2705 (2)	0.35218 (8)	0.2180 (1)	0.0367 (4)
C11	−0.0521 (2)	0.18540 (8)	0.4511 (1)	0.0333 (4)
C12	−0.1918 (2)	0.19626 (8)	0.3804 (1)	0.0367 (4)
C13	−0.2951 (2)	0.14779 (9)	0.3686 (1)	0.0394 (5)
C14	−0.2655 (2)	0.09109 (9)	0.4260 (1)	0.0413 (5)
C15	−0.1246 (2)	0.08138 (8)	0.4926 (1)	0.0405 (5)
C16	−0.0147 (2)	0.12788 (8)	0.5062 (1)	0.0348 (4)
C17	−0.2297 (2)	0.25928 (9)	0.3228 (1)	0.0482 (5)
C18	−0.3868 (2)	0.0431 (1)	0.4200 (2)	0.0585 (6)
C19	0.1364 (2)	0.11667 (9)	0.5804 (1)	0.0447 (5)
C20	0.0631 (2)	0.28480 (8)	0.5350 (1)	0.0389 (5)
C21	0.4479 (2)	0.44686 (8)	0.3662 (1)	0.0416 (5)
C22	0.5781 (2)	0.42840 (8)	0.4421 (1)	0.0445 (5)
C23	0.7105 (2)	0.44822 (9)	0.4314 (1)	0.0512 (5)
C24	0.7180 (2)	0.48541 (8)	0.3479 (2)	0.0522 (5)
C25	0.5875 (2)	0.50542 (8)	0.2774 (1)	0.0507 (5)
C26	0.4531 (2)	0.48781 (8)	0.2848 (1)	0.0458 (5)
C27	0.5768 (2)	0.3871 (1)	0.5323 (1)	0.0565 (6)
C28	0.8638 (3)	0.50104 (10)	0.3355 (2)	0.0688 (7)
C29	0.3119 (2)	0.51285 (9)	0.2080 (1)	0.0560 (6)
H1	0.0413	0.1718	0.2835	0.0421*
H2	0.2757	0.1666	0.2379	0.0476*
H3	0.4703	0.2301	0.3709	0.0458*
H4	0.3608	0.2749	0.5023	0.0402*
H5	0.0182	0.3789	0.3199	0.0511*
H6	−0.0656	0.3078	0.1596	0.0534*
H7	0.1485	0.2937	0.0919	0.0502*
H8	0.3661	0.3539	0.2122	0.0440*
H9	−0.3897	0.1536	0.3194	0.0473*
H10	−0.1020	0.0419	0.5302	0.0486*
H11	−0.3301	0.2589	0.2816	0.0579*
H12	−0.2125	0.2941	0.3708	0.0579*
H13	−0.1703	0.2647	0.2796	0.0579*
H14	−0.4720	0.0547	0.3648	0.0701*
H15	−0.4085	0.0437	0.4832	0.0701*
H16	−0.3562	0.0009	0.4084	0.0701*
H17	0.1580	0.1488	0.6330	0.0536*
H18	0.1409	0.0750	0.6108	0.0536*
H19	0.2059	0.1191	0.5445	0.0536*
H20	0.7993	0.4360	0.4829	0.0615*
H21	0.5902	0.5324	0.2217	0.0609*
H22	0.5309	0.3468	0.5079	0.0677*
H23	0.5240	0.4087	0.5707	0.0677*
H24	0.6747	0.3797	0.5755	0.0677*
H25	0.8701	0.4814	0.2742	0.0825*
H26	0.9402	0.4849	0.3934	0.0825*
H27	0.8735	0.5467	0.3313	0.0825*
H28	0.3340	0.5384	0.1570	0.0671*
H29	0.2611	0.5386	0.2432	0.0671*
H30	0.2520	0.4772	0.1758	0.0671*
H31	0.294 (2)	0.4239 (9)	0.426 (1)	0.0592*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0317 (1)	0.0298 (1)	0.0309 (1)	0.00331 (9)	0.01228 (9)	−0.00094 (9)
Cl1	0.0442 (3)	0.0686 (3)	0.0467 (3)	−0.0006 (2)	0.0261 (2)	−0.0144 (2)
S1	0.0796 (4)	0.0466 (3)	0.0607 (3)	−0.0196 (3)	0.0407 (3)	−0.0224 (2)
N1	0.0314 (7)	0.0340 (7)	0.0315 (7)	0.0008 (5)	0.0135 (6)	−0.0033 (5)
N2	0.0600 (9)	0.0361 (8)	0.0367 (8)	0.0001 (7)	0.0196 (7)	−0.0052 (6)
C1	0.0303 (8)	0.0282 (8)	0.0332 (8)	0.0021 (6)	0.0137 (7)	0.0004 (6)
C2	0.0395 (9)	0.0300 (8)	0.0382 (9)	−0.0023 (7)	0.0159 (7)	−0.0045 (7)
C3	0.051 (1)	0.0298 (8)	0.0489 (10)	0.0048 (7)	0.0306 (8)	−0.0026 (7)
C4	0.0326 (9)	0.0351 (9)	0.0520 (10)	0.0082 (6)	0.0210 (7)	0.0088 (7)
C5	0.0313 (8)	0.0341 (9)	0.0341 (8)	0.0025 (7)	0.0090 (7)	0.0056 (7)
C6	0.0479 (9)	0.0287 (7)	0.0348 (8)	0.0087 (7)	0.0140 (7)	0.0040 (6)
C7	0.0450 (9)	0.0389 (9)	0.0444 (9)	0.0168 (7)	0.0150 (8)	0.0055 (7)
C8	0.0377 (9)	0.049 (1)	0.0424 (9)	0.0078 (8)	0.0061 (7)	0.0077 (7)
C9	0.049 (1)	0.0430 (10)	0.0313 (8)	0.0030 (8)	0.0104 (7)	0.0010 (7)
C10	0.0438 (10)	0.0340 (9)	0.0340 (8)	0.0008 (7)	0.0150 (7)	0.0021 (6)
C11	0.0300 (8)	0.0409 (9)	0.0345 (8)	−0.0029 (6)	0.0179 (6)	−0.0063 (7)
C12	0.0326 (8)	0.0454 (9)	0.0355 (9)	0.0033 (7)	0.0159 (7)	−0.0052 (7)
C13	0.0248 (8)	0.0576 (10)	0.0367 (9)	0.0004 (7)	0.0110 (7)	−0.0101 (7)
C14	0.0366 (9)	0.0498 (10)	0.0424 (9)	−0.0092 (7)	0.0193 (7)	−0.0106 (7)
C15	0.0406 (9)	0.0434 (9)	0.0405 (9)	−0.0044 (7)	0.0175 (8)	−0.0025 (8)
C16	0.0334 (8)	0.0415 (9)	0.0324 (8)	−0.0023 (7)	0.0146 (7)	−0.0035 (7)
C17	0.035 (1)	0.055 (1)	0.051 (1)	0.0072 (8)	0.0092 (9)	0.0041 (9)
C18	0.045 (1)	0.071 (1)	0.064 (1)	−0.0215 (10)	0.022 (1)	−0.010 (1)
C19	0.0407 (9)	0.046 (1)	0.0445 (10)	−0.0040 (8)	0.0091 (8)	0.0055 (8)
C20	0.0420 (9)	0.0442 (9)	0.0344 (9)	0.0015 (7)	0.0178 (7)	−0.0030 (7)
C21	0.061 (1)	0.0256 (8)	0.0386 (9)	0.0001 (7)	0.0172 (8)	−0.0065 (7)
C22	0.062 (1)	0.0301 (9)	0.0377 (9)	−0.0047 (8)	0.0111 (8)	−0.0062 (7)
C23	0.059 (1)	0.0363 (10)	0.052 (1)	−0.0026 (8)	0.0095 (10)	−0.0106 (8)
C24	0.074 (1)	0.0299 (9)	0.062 (1)	−0.0054 (8)	0.0332 (9)	−0.0139 (8)
C25	0.083 (1)	0.0291 (9)	0.046 (1)	−0.0003 (9)	0.0289 (10)	−0.0005 (8)
C26	0.074 (1)	0.0240 (8)	0.0413 (9)	0.0014 (8)	0.0204 (9)	−0.0020 (7)
C27	0.066 (1)	0.054 (1)	0.0398 (10)	−0.008 (1)	0.0035 (10)	0.0030 (8)
C28	0.082 (2)	0.045 (1)	0.094 (2)	−0.003 (1)	0.049 (1)	−0.011 (1)
C29	0.084 (1)	0.0355 (10)	0.046 (1)	0.0094 (10)	0.0168 (10)	0.0071 (8)

Geometric parameters (Å, º)

Fe1—C1	2.045 (2)	C22—C23	1.390 (4)
Fe1—C2	2.041 (2)	C22—C27	1.501 (3)
Fe1—C3	2.040 (2)	C23—C24	1.395 (4)
Fe1—C4	2.042 (2)	C24—C25	1.379 (4)
Fe1—C5	2.054 (2)	C24—C28	1.501 (4)
Fe1—C6	2.099 (2)	C25—C26	1.377 (4)
Fe1—C7	2.053 (2)	C26—C29	1.517 (4)
Fe1—C8	2.027 (2)	N2—H31	0.83 (2)
Fe1—C9	2.043 (2)	C2—H1	0.950
Fe1—C10	2.058 (2)	C3—H2	0.949
Cl1—C20	1.762 (2)	C4—H3	0.950
S1—C20	1.638 (2)	C5—H4	0.951
N1—C1	1.439 (3)	C7—H5	0.950
N1—C11	1.454 (3)	C8—H6	0.949
N1—C20	1.343 (3)	C9—H7	0.949
N2—C6	1.408 (3)	C10—H8	0.950
N2—C21	1.419 (3)	C13—H9	0.950
C1—C2	1.436 (3)	C15—H10	0.951
C1—C5	1.420 (3)	C17—H11	0.950
C2—C3	1.409 (3)	C17—H12	0.951
C3—C4	1.410 (3)	C17—H13	0.950
C4—C5	1.412 (3)	C18—H14	0.952
C6—C7	1.419 (3)	C18—H15	0.948
C6—C10	1.419 (3)	C18—H16	0.950
C7—C8	1.426 (3)	C19—H17	0.950
C8—C9	1.415 (3)	C19—H18	0.949
C9—C10	1.419 (3)	C19—H19	0.951
C11—C12	1.400 (3)	C23—H20	0.951
C11—C16	1.389 (3)	C25—H21	0.949
C12—C13	1.383 (3)	C27—H22	0.951
C12—C17	1.502 (3)	C27—H23	0.949
C13—C14	1.386 (3)	C27—H24	0.950
C14—C15	1.384 (3)	C28—H25	0.951
C14—C18	1.512 (3)	C28—H26	0.949
C15—C16	1.395 (3)	C28—H27	0.950
C16—C19	1.500 (3)	C29—H28	0.949
C21—C22	1.399 (3)	C29—H29	0.950
C21—C26	1.410 (3)	C29—H30	0.949
S1···N2	3.702 (2)	C4···C13^ii	3.576 (3)
S1···C28^i	3.484 (3)
C1—Fe1—C2	41.15 (8)	C13—C14—C18	120.4 (2)
C1—Fe1—C3	68.16 (8)	C15—C14—C18	121.2 (2)
C1—Fe1—C4	67.87 (8)	C14—C15—C16	122.0 (2)
C1—Fe1—C5	40.55 (8)	C11—C16—C15	117.5 (2)
C1—Fe1—C6	127.20 (8)	C11—C16—C19	121.6 (2)
C1—Fe1—C7	108.93 (9)	C15—C16—C19	120.9 (2)
C1—Fe1—C8	120.94 (9)	Cl1—C20—S1	117.8 (1)
C1—Fe1—C9	155.27 (9)	Cl1—C20—N1	113.0 (2)
C1—Fe1—C10	163.26 (8)	S1—C20—N1	129.2 (2)
C2—Fe1—C3	40.38 (9)	N2—C21—C22	121.8 (2)
C2—Fe1—C4	68.18 (9)	N2—C21—C26	118.4 (2)
C2—Fe1—C5	68.78 (9)	C22—C21—C26	119.8 (2)
C2—Fe1—C6	164.44 (9)	C21—C22—C23	118.4 (2)
C2—Fe1—C7	126.96 (10)	C21—C22—C27	121.4 (2)
C2—Fe1—C8	107.72 (10)	C23—C22—C27	120.2 (2)
C2—Fe1—C9	119.49 (9)	C22—C23—C24	122.5 (3)
C2—Fe1—C10	153.95 (9)	C23—C24—C25	117.4 (3)
C3—Fe1—C4	40.42 (9)	C23—C24—C28	120.3 (3)
C3—Fe1—C5	68.17 (9)	C25—C24—C28	122.2 (3)
C3—Fe1—C6	154.39 (10)	C24—C25—C26	122.5 (2)
C3—Fe1—C7	163.76 (10)	C21—C26—C25	119.1 (2)
C3—Fe1—C8	125.70 (10)	C21—C26—C29	119.9 (2)
C3—Fe1—C9	107.22 (9)	C25—C26—C29	121.0 (2)
C3—Fe1—C10	119.69 (9)	C6—N2—H31	113 (1)
C4—Fe1—C5	40.32 (9)	C21—N2—H31	120 (1)
C4—Fe1—C6	120.68 (9)	Fe1—C2—H1	125.976
C4—Fe1—C7	154.83 (10)	C1—C2—H1	126.358
C4—Fe1—C8	162.66 (10)	C3—C2—H1	126.490
C4—Fe1—C9	125.34 (10)	Fe1—C3—H2	126.055
C4—Fe1—C10	107.66 (9)	C2—C3—H2	125.701
C5—Fe1—C6	108.86 (8)	C4—C3—H2	125.739
C5—Fe1—C7	120.78 (9)	Fe1—C4—H3	125.919
C5—Fe1—C8	155.67 (9)	C3—C4—H3	125.455
C5—Fe1—C9	162.41 (9)	C5—C4—H3	125.758
C5—Fe1—C10	125.72 (9)	Fe1—C5—H4	126.543
C6—Fe1—C7	39.96 (9)	C1—C5—H4	126.332
C6—Fe1—C8	67.69 (9)	C4—C5—H4	126.357
C6—Fe1—C9	67.49 (9)	Fe1—C7—H5	125.110
C6—Fe1—C10	39.90 (8)	C6—C7—H5	126.113
C7—Fe1—C8	40.89 (9)	C8—C7—H5	126.070
C7—Fe1—C9	68.33 (9)	Fe1—C8—H6	124.893
C7—Fe1—C10	67.80 (9)	C7—C8—H6	125.876
C8—Fe1—C9	40.68 (10)	C9—C8—H6	125.964
C8—Fe1—C10	68.16 (9)	Fe1—C9—H7	125.896
C9—Fe1—C10	40.48 (9)	C8—C9—H7	126.102
C1—N1—C11	115.8 (2)	C10—C9—H7	126.094
C1—N1—C20	123.2 (2)	Fe1—C10—H8	125.036
C11—N1—C20	121.0 (2)	C6—C10—H8	125.896
C6—N2—C21	119.1 (2)	C9—C10—H8	125.735
Fe1—C1—N1	131.5 (1)	C12—C13—H9	118.760
Fe1—C1—C2	69.3 (1)	C14—C13—H9	118.939
Fe1—C1—C5	70.1 (1)	C14—C15—H10	119.013
N1—C1—C2	122.5 (2)	C16—C15—H10	119.020
N1—C1—C5	128.9 (2)	C12—C17—H11	109.527
C2—C1—C5	108.2 (2)	C12—C17—H12	109.571
Fe1—C2—C1	69.5 (1)	C12—C17—H13	109.608
Fe1—C2—C3	69.8 (1)	H11—C17—H12	109.350
C1—C2—C3	107.2 (2)	H11—C17—H13	109.428
Fe1—C3—C2	69.9 (1)	H12—C17—H13	109.342
Fe1—C3—C4	69.9 (1)	C14—C18—H14	109.436
C2—C3—C4	108.6 (2)	C14—C18—H15	109.589
Fe1—C4—C3	69.7 (1)	C14—C18—H16	109.465
Fe1—C4—C5	70.3 (1)	H14—C18—H15	109.434
C3—C4—C5	108.8 (2)	H14—C18—H16	109.298
Fe1—C5—C1	69.4 (1)	H15—C18—H16	109.605
Fe1—C5—C4	69.4 (1)	C16—C19—H17	109.485
C1—C5—C4	107.3 (2)	C16—C19—H18	109.555
Fe1—C6—N2	131.4 (2)	C16—C19—H19	109.398
Fe1—C6—C7	68.3 (1)	H17—C19—H18	109.532
Fe1—C6—C10	68.5 (1)	H17—C19—H19	109.396
N2—C6—C7	126.2 (2)	H18—C19—H19	109.461
N2—C6—C10	125.9 (2)	C22—C23—H20	118.733
C7—C6—C10	107.8 (2)	C24—C23—H20	118.794
Fe1—C7—C6	71.7 (1)	C24—C25—H21	118.821
Fe1—C7—C8	68.6 (1)	C26—C25—H21	118.690
C6—C7—C8	107.8 (2)	C22—C27—H22	109.491
Fe1—C8—C7	70.5 (1)	C22—C27—H23	109.505
Fe1—C8—C9	70.2 (1)	C22—C27—H24	109.445
C7—C8—C9	108.2 (2)	H22—C27—H23	109.489
Fe1—C9—C8	69.1 (1)	H22—C27—H24	109.377
Fe1—C9—C10	70.3 (1)	H23—C27—H24	109.521
C8—C9—C10	107.8 (2)	C24—C28—H25	109.469
Fe1—C10—C6	71.6 (1)	C24—C28—H26	109.509
Fe1—C10—C9	69.2 (1)	C24—C28—H27	109.436
C6—C10—C9	108.4 (2)	H25—C28—H26	109.497
N1—C11—C12	119.1 (2)	H25—C28—H27	109.397
N1—C11—C16	118.5 (2)	H26—C28—H27	109.520
C12—C11—C16	122.4 (2)	C26—C29—H28	109.361
C11—C12—C13	117.4 (2)	C26—C29—H29	109.305
C11—C12—C17	121.2 (2)	C26—C29—H30	109.455
C13—C12—C17	121.3 (2)	H28—C29—H29	109.517
C12—C13—C14	122.3 (2)	H28—C29—H30	109.643
C13—C14—C15	118.3 (2)	H29—C29—H30	109.546
Fe1—C1—N1—C11	113.5 (2)	C3—Fe1—C6—C7	165.6 (2)
Fe1—C1—N1—C20	−69.1 (3)	C3—Fe1—C6—C10	44.9 (3)
Fe1—C1—C2—C3	59.9 (1)	C3—Fe1—C7—C6	−157.4 (3)
Fe1—C1—C5—C4	−59.2 (1)	C3—Fe1—C7—C8	−39.0 (4)
Fe1—C2—C1—N1	126.8 (2)	C3—Fe1—C8—C7	167.5 (1)
Fe1—C2—C1—C5	−59.5 (1)	C3—Fe1—C8—C9	−73.9 (2)
Fe1—C2—C3—C4	59.3 (2)	C3—Fe1—C9—C8	125.2 (1)
Fe1—C3—C2—C1	−59.8 (1)	C3—Fe1—C9—C10	−115.8 (1)
Fe1—C3—C4—C5	59.6 (2)	C3—Fe1—C10—C6	−159.4 (1)
Fe1—C4—C3—C2	−59.3 (2)	C3—Fe1—C10—C9	81.8 (2)
Fe1—C4—C5—C1	59.2 (1)	C3—C2—Fe1—C4	−37.3 (1)
Fe1—C5—C1—N1	−127.8 (2)	C3—C2—Fe1—C5	−80.8 (1)
Fe1—C5—C1—C2	59.0 (1)	C3—C2—Fe1—C6	−165.0 (3)
Fe1—C5—C4—C3	−59.3 (2)	C3—C2—Fe1—C7	165.9 (1)
Fe1—C6—N2—C21	97.7 (2)	C3—C2—Fe1—C8	124.7 (1)
Fe1—C6—C7—C8	−59.3 (2)	C3—C2—Fe1—C9	82.0 (2)
Fe1—C6—C10—C9	59.7 (1)	C3—C2—Fe1—C10	48.4 (3)
Fe1—C7—C6—N2	−126.2 (2)	C3—C2—C1—C5	0.4 (2)
Fe1—C7—C6—C10	57.2 (1)	C3—C4—Fe1—C5	119.8 (2)
Fe1—C7—C8—C9	−60.4 (2)	C3—C4—Fe1—C6	−157.0 (1)
Fe1—C8—C7—C6	61.3 (2)	C3—C4—Fe1—C7	169.4 (2)
Fe1—C8—C9—C10	−59.9 (2)	C3—C4—Fe1—C8	−42.2 (4)
Fe1—C9—C8—C7	60.6 (2)	C3—C4—Fe1—C9	−74.2 (2)
Fe1—C9—C10—C6	−61.2 (1)	C3—C4—Fe1—C10	−115.3 (1)
Fe1—C10—C6—N2	126.3 (2)	C4—Fe1—C1—C5	37.8 (1)
Fe1—C10—C6—C7	−57.1 (2)	C4—Fe1—C6—C7	−158.5 (1)
Fe1—C10—C9—C8	59.1 (2)	C4—Fe1—C6—C10	80.8 (1)
Cl1—C20—N1—C1	−175.8 (2)	C4—Fe1—C7—C6	47.8 (3)
Cl1—C20—N1—C11	1.5 (3)	C4—Fe1—C7—C8	166.2 (2)
S1—C20—N1—C1	3.4 (3)	C4—Fe1—C8—C7	−160.1 (3)
S1—C20—N1—C11	−179.3 (2)	C4—Fe1—C8—C9	−41.5 (4)
N1—C1—Fe1—C2	−115.6 (2)	C4—Fe1—C9—C8	166.0 (1)
N1—C1—Fe1—C3	−153.6 (2)	C4—Fe1—C9—C10	−75.1 (2)
N1—C1—Fe1—C4	162.7 (2)	C4—Fe1—C10—C6	−117.0 (1)
N1—C1—Fe1—C5	124.9 (2)	C4—Fe1—C10—C9	124.2 (1)
N1—C1—Fe1—C6	50.1 (2)	C4—C3—Fe1—C5	−37.2 (1)
N1—C1—Fe1—C7	9.3 (2)	C4—C3—Fe1—C6	51.0 (3)
N1—C1—Fe1—C8	−34.1 (2)	C4—C3—Fe1—C7	−163.8 (3)
N1—C1—Fe1—C9	−69.8 (3)	C4—C3—Fe1—C8	165.7 (1)
N1—C1—Fe1—C10	85.1 (4)	C4—C3—Fe1—C9	124.7 (1)
N1—C1—C2—C3	−173.3 (2)	C4—C3—Fe1—C10	82.5 (1)
N1—C1—C5—C4	172.9 (2)	C4—C5—Fe1—C6	−115.5 (1)
N1—C11—C12—C13	−177.8 (2)	C4—C5—Fe1—C7	−157.8 (1)
N1—C11—C12—C17	−0.3 (3)	C4—C5—Fe1—C8	167.1 (2)
N1—C11—C16—C15	176.4 (2)	C4—C5—Fe1—C9	−40.7 (3)
N1—C11—C16—C19	−1.5 (3)	C4—C5—Fe1—C10	−74.4 (2)
N2—C6—Fe1—C1	45.5 (3)	C5—Fe1—C6—C7	−115.7 (1)
N2—C6—Fe1—C2	82.5 (4)	C5—Fe1—C6—C10	123.6 (1)
N2—C6—Fe1—C3	−74.6 (3)	C5—Fe1—C7—C6	82.8 (1)
N2—C6—Fe1—C4	−38.7 (3)	C5—Fe1—C7—C8	−158.8 (1)
N2—C6—Fe1—C5	4.0 (2)	C5—Fe1—C8—C7	49.0 (3)
N2—C6—Fe1—C7	119.8 (3)	C5—Fe1—C8—C9	167.5 (2)
N2—C6—Fe1—C8	158.3 (2)	C5—Fe1—C9—C8	−162.9 (3)
N2—C6—Fe1—C9	−157.6 (2)	C5—Fe1—C9—C10	−43.9 (3)
N2—C6—Fe1—C10	−119.6 (3)	C5—Fe1—C10—C6	−76.2 (2)
N2—C6—C7—C8	174.4 (2)	C5—Fe1—C10—C9	165.0 (1)
N2—C6—C10—C9	−174.0 (2)	C5—C1—Fe1—C6	−74.8 (2)
N2—C21—C22—C23	178.2 (2)	C5—C1—Fe1—C7	−115.6 (1)
N2—C21—C22—C27	−0.7 (3)	C5—C1—Fe1—C8	−159.0 (1)
N2—C21—C26—C25	−177.4 (2)	C5—C1—Fe1—C9	165.3 (2)
N2—C21—C26—C29	3.8 (3)	C5—C1—Fe1—C10	−39.8 (3)
C1—Fe1—C2—C3	−118.2 (2)	C5—C1—N1—C11	−149.0 (2)
C1—Fe1—C3—C2	38.7 (1)	C5—C1—N1—C20	28.4 (3)
C1—Fe1—C3—C4	−81.1 (1)	C5—C4—Fe1—C6	83.2 (1)
C1—Fe1—C4—C3	81.8 (1)	C5—C4—Fe1—C7	49.6 (3)
C1—Fe1—C4—C5	−38.0 (1)	C5—C4—Fe1—C8	−162.0 (3)
C1—Fe1—C5—C4	118.8 (2)	C5—C4—Fe1—C9	166.0 (1)
C1—Fe1—C6—C7	−74.2 (2)	C5—C4—Fe1—C10	124.9 (1)
C1—Fe1—C6—C10	165.1 (1)	C6—Fe1—C7—C8	118.4 (2)
C1—Fe1—C7—C6	125.9 (1)	C6—Fe1—C8—C7	−37.6 (1)
C1—Fe1—C7—C8	−115.7 (1)	C6—Fe1—C8—C9	80.9 (1)
C1—Fe1—C8—C7	83.4 (2)	C6—Fe1—C9—C8	−81.5 (2)
C1—Fe1—C8—C9	−158.0 (1)	C6—Fe1—C9—C10	37.5 (1)
C1—Fe1—C9—C8	50.2 (3)	C6—Fe1—C10—C9	−118.8 (2)
C1—Fe1—C9—C10	169.1 (2)	C6—N2—C21—C22	−112.1 (2)
C1—Fe1—C10—C6	−45.3 (3)	C6—N2—C21—C26	69.7 (3)
C1—Fe1—C10—C9	−164.1 (3)	C6—C7—Fe1—C8	−118.4 (2)
C1—N1—C11—C12	−99.0 (2)	C6—C7—Fe1—C9	−80.4 (1)
C1—N1—C11—C16	81.4 (2)	C6—C7—Fe1—C10	−36.6 (1)
C1—C2—Fe1—C3	118.2 (2)	C6—C7—C8—C9	0.9 (3)
C1—C2—Fe1—C4	80.9 (1)	C6—C10—Fe1—C7	36.6 (1)
C1—C2—Fe1—C5	37.4 (1)	C6—C10—Fe1—C8	80.9 (1)
C1—C2—Fe1—C6	−46.8 (4)	C6—C10—Fe1—C9	118.8 (2)
C1—C2—Fe1—C7	−75.9 (2)	C6—C10—C9—C8	−2.0 (2)
C1—C2—Fe1—C8	−117.0 (1)	C7—Fe1—C6—C10	−120.7 (2)
C1—C2—Fe1—C9	−159.8 (1)	C7—Fe1—C8—C9	118.6 (2)
C1—C2—Fe1—C10	166.6 (2)	C7—Fe1—C9—C8	−38.2 (1)
C1—C2—C3—C4	−0.4 (2)	C7—Fe1—C9—C10	80.7 (1)
C1—C5—Fe1—C2	−37.9 (1)	C7—Fe1—C10—C9	−82.2 (1)
C1—C5—Fe1—C3	−81.5 (1)	C7—C6—Fe1—C8	38.5 (1)
C1—C5—Fe1—C4	−118.8 (2)	C7—C6—Fe1—C9	82.7 (1)
C1—C5—Fe1—C6	125.7 (1)	C7—C6—Fe1—C10	120.7 (2)
C1—C5—Fe1—C7	83.4 (1)	C7—C6—N2—C21	−170.3 (2)
C1—C5—Fe1—C8	48.3 (3)	C7—C6—C10—C9	2.6 (2)
C1—C5—Fe1—C9	−159.4 (3)	C7—C8—Fe1—C9	−118.6 (2)
C1—C5—Fe1—C10	166.9 (1)	C7—C8—Fe1—C10	−80.8 (2)
C1—C5—C4—C3	−0.1 (2)	C7—C8—C9—C10	0.7 (3)
C2—Fe1—C1—C5	119.4 (2)	C8—Fe1—C6—C10	−82.2 (1)
C2—Fe1—C3—C4	−119.7 (2)	C8—Fe1—C9—C10	119.0 (2)
C2—Fe1—C4—C3	37.3 (1)	C8—Fe1—C10—C9	−37.9 (1)
C2—Fe1—C4—C5	−82.5 (1)	C8—C7—Fe1—C9	38.0 (1)
C2—Fe1—C5—C4	80.9 (1)	C8—C7—Fe1—C10	81.8 (2)
C2—Fe1—C6—C7	−37.2 (4)	C8—C7—C6—C10	−2.1 (2)
C2—Fe1—C6—C10	−157.9 (3)	C8—C9—Fe1—C10	−119.0 (2)
C2—Fe1—C7—C6	168.3 (1)	C9—Fe1—C6—C10	−38.0 (1)
C2—Fe1—C7—C8	−73.3 (2)	C9—C8—Fe1—C10	37.7 (1)
C2—Fe1—C8—C7	126.5 (1)	C10—C6—N2—C21	5.6 (3)
C2—Fe1—C8—C9	−114.9 (1)	C11—C12—C13—C14	1.9 (3)
C2—Fe1—C9—C8	83.0 (2)	C11—C16—C15—C14	0.9 (3)
C2—Fe1—C9—C10	−158.0 (1)	C12—C11—N1—C20	83.5 (3)
C2—Fe1—C10—C6	166.7 (2)	C12—C11—C16—C15	−3.1 (3)
C2—Fe1—C10—C9	47.9 (3)	C12—C11—C16—C19	179.0 (2)
C2—C1—Fe1—C3	−37.9 (1)	C12—C13—C14—C15	−4.1 (3)
C2—C1—Fe1—C4	−81.7 (1)	C12—C13—C14—C18	172.5 (2)
C2—C1—Fe1—C5	−119.4 (2)	C13—C12—C11—C16	1.8 (3)
C2—C1—Fe1—C6	165.8 (1)	C13—C14—C15—C16	2.6 (3)
C2—C1—Fe1—C7	125.0 (1)	C14—C13—C12—C17	−175.5 (2)
C2—C1—Fe1—C8	81.6 (1)	C14—C15—C16—C19	178.8 (2)
C2—C1—Fe1—C9	45.9 (3)	C16—C11—N1—C20	−96.1 (2)
C2—C1—Fe1—C10	−159.3 (3)	C16—C11—C12—C17	179.3 (2)
C2—C1—N1—C11	23.3 (3)	C16—C15—C14—C18	−173.9 (2)
C2—C1—N1—C20	−159.3 (2)	C21—C22—C23—C24	−0.3 (3)
C2—C1—C5—C4	−0.2 (2)	C21—C26—C25—C24	−1.2 (4)
C2—C3—Fe1—C4	119.7 (2)	C22—C21—C26—C25	4.4 (3)
C2—C3—Fe1—C5	82.5 (1)	C22—C21—C26—C29	−174.4 (2)
C2—C3—Fe1—C6	170.8 (2)	C22—C23—C24—C25	3.5 (4)
C2—C3—Fe1—C7	−44.1 (4)	C22—C23—C24—C28	−175.1 (2)
C2—C3—Fe1—C8	−74.6 (2)	C23—C22—C21—C26	−3.7 (3)
C2—C3—Fe1—C9	−115.5 (1)	C23—C24—C25—C26	−2.7 (4)
C2—C3—Fe1—C10	−157.8 (1)	C24—C23—C22—C27	178.6 (2)
C2—C3—C4—C5	0.3 (3)	C24—C25—C26—C29	177.7 (2)
C3—Fe1—C1—C5	81.5 (1)	C26—C21—C22—C27	177.5 (2)
C3—Fe1—C4—C5	−119.8 (2)	C26—C25—C24—C28	175.8 (2)
C3—Fe1—C5—C4	37.3 (1)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z.