rac-{[2-(Diphenyl-thio-phosphan-yl)ferrocen-yl]meth-yl}trimethyl-ammonium iodide chloro-form monosolvate.

The title compound, [Fe(C5H5)(C21H24NPS)]I·CHCl3, is built up from a (ferrocenylmeth-yl)trimethyl-ammonium cation, a iodine anion and a chloro-form solvent mol-ecule, all residing in general positions. The N atom of the ammonium group is displaced by 1.182 (2) Å from the plane of the substituted cyclo-penta-dienyl (Cp) ring towards the Fe atom, whereas the C atom attached to the same Cp ring is slightly below this plane by -0.128 (2) Å. These deviations might result from weak agostic interactions between the two H atoms of the CH2 group and the Fe atom.

Related literature

For related structures containing the (ferrocen­yl)trimethyl­ammonium framework, see: Bai et al. (2011 ▶); Ballester et al. (2003 ▶); Blake et al. (2004 ▶); Broomsgrove et al. (2010 ▶); Chohan et al. (1997 ▶); Deck et al. (2000 ▶); Ferguson et al. (1994 ▶); Herbstein & Kapon (2008 ▶); Hong et al. (2005 ▶); Hosmane et al. (1998 ▶); Hu et al. (2004 ▶); Li et al. (2009 ▶); Malezieux et al. (1994 ▶); Pullen et al. (1998 ▶); Reynes et al. (2002 ▶); Selvapalam et al. (2007 ▶); Sharma et al. (2006 ▶); Veya & Kochi (1995 ▶); Volkov et al. (2003 ▶, 2005 ▶, 2006 ▶); Xu et al. (2010 ▶); Yongmao et al. (1982 ▶); Zhuji et al. (1982 ▶). For their use in chemistry, see: Routaboul et al. (2005 ▶, 2007 ▶); Mateus et al. (2006 ▶); Le Roux et al. (2007 ▶); Diab et al. (2008 ▶); Audin et al. (2010 ▶); Debono et al. (2010 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

[Fe(C5H5)(C21H24NPS)]I·CHCl3

M = 720.65

Monoclinic,

a = 17.4056 (6) Å

b = 12.1843 (3) Å

c = 14.9389 (5) Å

β = 110.632 (4)°

V = 2964.97 (18) Å3

Z = 4

Mo Kα radiation

μ = 1.96 mm−1

T = 180 K

0.49 × 0.18 × 0.10 mm

Data collection

Agilent Xcalibur (Sapphire1, long nozzle) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.574, T max = 1.0

31103 measured reflections

6065 independent reflections

5385 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.062

S = 1.08

6065 reflections

319 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.61 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046053/rn2109sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046053/rn2109Isup2.hkl

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

[Fe(C5H5)(C21H24NPS)]I·CHCl3	F(000) = 1440
Mr = 720.65	Dx = 1.614 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19830 reflections
a = 17.4056 (6) Å	θ = 2.9–28.4°
b = 12.1843 (3) Å	µ = 1.96 mm−1
c = 14.9389 (5) Å	T = 180 K
β = 110.632 (4)°	Box, yellow
V = 2964.97 (18) Å3	0.49 × 0.18 × 0.10 mm
Z = 4

Agilent Xcalibur (Sapphire1, long nozzle) diffractometer	6065 independent reflections
Radiation source: fine-focus sealed tube	5385 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 8.2632 pixels mm-1	θmax = 26.4°, θmin = 2.9°
ω scans	h = −21→21
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −15→15
Tmin = 0.574, Tmax = 1.0	l = −18→18
31103 measured reflections

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0242P)2 + 2.8471P] where P = (Fo2 + 2Fc2)/3
6065 reflections	(Δ/σ)max = 0.002
319 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.61 e Å−3

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. CrysAlisPro (Agilent Technologies, 2012)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Fe1	0.170301 (18)	0.73893 (3)	0.16941 (2)	0.01825 (7)
P1	0.13712 (3)	0.49498 (4)	0.25844 (4)	0.01734 (11)
S1	0.13878 (4)	0.39785 (5)	0.15519 (4)	0.02843 (13)
N1	0.38708 (12)	0.51750 (17)	0.26266 (14)	0.0266 (4)
C1	0.19359 (13)	0.62039 (17)	0.26970 (14)	0.0173 (4)
C2	0.26568 (13)	0.64348 (18)	0.24522 (15)	0.0196 (4)
C3	0.28607 (14)	0.75593 (19)	0.26702 (16)	0.0242 (5)
H3	0.3307	0.7935	0.2581	0.029*
C4	0.22953 (15)	0.80223 (19)	0.30379 (16)	0.0253 (5)
H4	0.2297	0.8762	0.3241	0.030*
C5	0.17231 (14)	0.72073 (17)	0.30565 (15)	0.0211 (4)
H5	0.1274	0.7307	0.3270	0.025*
C6	0.06407 (17)	0.7065 (2)	0.05634 (18)	0.0407 (7)
H6	0.0244	0.6519	0.0537	0.049*
C7	0.13415 (18)	0.6930 (2)	0.03003 (17)	0.0367 (6)
H7	0.1500	0.6273	0.0070	0.044*
C8	0.17626 (15)	0.7942 (2)	0.04407 (16)	0.0292 (5)
H8	0.2253	0.8089	0.0319	0.035*
C9	0.13258 (15)	0.8694 (2)	0.07938 (17)	0.0309 (5)
H9	0.1471	0.9439	0.0954	0.037*
C10	0.06381 (16)	0.8155 (3)	0.08696 (18)	0.0377 (6)
H10	0.0239	0.8473	0.1090	0.045*
C21	0.30886 (13)	0.57269 (19)	0.19659 (15)	0.0231 (5)
H21A	0.3230	0.6180	0.1496	0.028*
H21B	0.2704	0.5149	0.1605	0.028*
C23	0.42053 (19)	0.4499 (3)	0.2013 (2)	0.0448 (7)
H23A	0.4707	0.4127	0.2417	0.067*
H23B	0.4331	0.4975	0.1554	0.067*
H23C	0.3797	0.3950	0.1667	0.067*
C24	0.36912 (17)	0.4455 (2)	0.3336 (2)	0.0409 (7)
H24A	0.3253	0.3939	0.2999	0.061*
H24B	0.3516	0.4907	0.3772	0.061*
H24C	0.4187	0.4045	0.3703	0.061*
C25	0.45051 (16)	0.6000 (2)	0.3157 (2)	0.0396 (6)
H25A	0.4302	0.6429	0.3581	0.059*
H25B	0.4618	0.6491	0.2699	0.059*
H25C	0.5011	0.5619	0.3537	0.059*
C111	0.17654 (13)	0.43111 (17)	0.37555 (15)	0.0186 (4)
C112	0.23704 (14)	0.47914 (18)	0.45243 (15)	0.0214 (4)
H112	0.2616	0.5462	0.4442	0.026*
C113	0.26174 (15)	0.4291 (2)	0.54143 (16)	0.0269 (5)
H113	0.3040	0.4611	0.5940	0.032*
C114	0.22482 (15)	0.3329 (2)	0.55350 (16)	0.0289 (5)
H114	0.2411	0.2995	0.6148	0.035*
C115	0.16466 (15)	0.2848 (2)	0.47744 (17)	0.0285 (5)
H115	0.1396	0.2185	0.4864	0.034*
C116	0.14071 (14)	0.33311 (19)	0.38783 (16)	0.0240 (5)
H116	0.0999	0.2993	0.3350	0.029*
C121	0.03365 (13)	0.53257 (17)	0.24974 (15)	0.0204 (4)
C122	0.01987 (14)	0.57870 (19)	0.32821 (16)	0.0243 (5)
H122	0.0646	0.5903	0.3863	0.029*
C123	−0.05875 (15)	0.6075 (2)	0.32155 (19)	0.0313 (5)
H123	−0.0678	0.6403	0.3747	0.038*
C124	−0.12427 (16)	0.5887 (2)	0.2378 (2)	0.0359 (6)
H124	−0.1782	0.6088	0.2333	0.043*
C125	−0.11120 (15)	0.5408 (2)	0.16082 (19)	0.0348 (6)
H125	−0.1564	0.5272	0.1036	0.042*
C126	−0.03235 (15)	0.51233 (19)	0.16629 (17)	0.0270 (5)
H126	−0.0237	0.4791	0.1131	0.032*
C100	0.40211 (16)	0.1117 (2)	0.40949 (18)	0.0339 (6)
H100	0.4611	0.1343	0.4362	0.041*
Cl1	0.39374 (5)	−0.02380 (6)	0.44430 (6)	0.04887 (18)
Cl2	0.34498 (6)	0.19884 (7)	0.45463 (7)	0.0642 (3)
Cl3	0.36757 (5)	0.12290 (10)	0.28457 (5)	0.0685 (3)
I1	0.586539 (10)	0.293348 (13)	0.433624 (12)	0.03129 (6)

	U11	U22	U33	U12	U13	U23
Fe1	0.01707 (16)	0.01936 (16)	0.01709 (15)	−0.00029 (12)	0.00449 (12)	0.00296 (12)
P1	0.0202 (3)	0.0167 (3)	0.0162 (2)	−0.0016 (2)	0.0079 (2)	−0.0016 (2)
S1	0.0382 (3)	0.0255 (3)	0.0257 (3)	−0.0051 (3)	0.0164 (3)	−0.0105 (2)
N1	0.0222 (10)	0.0349 (11)	0.0263 (10)	0.0080 (9)	0.0128 (8)	0.0060 (9)
C1	0.0195 (10)	0.0176 (10)	0.0141 (9)	−0.0006 (8)	0.0050 (8)	0.0013 (8)
C2	0.0179 (10)	0.0214 (11)	0.0177 (10)	−0.0007 (9)	0.0041 (8)	0.0040 (8)
C3	0.0210 (11)	0.0237 (11)	0.0241 (11)	−0.0042 (9)	0.0031 (9)	0.0031 (9)
C4	0.0280 (12)	0.0191 (11)	0.0242 (11)	−0.0026 (9)	0.0037 (10)	−0.0022 (9)
C5	0.0246 (11)	0.0212 (11)	0.0167 (10)	0.0006 (9)	0.0064 (9)	−0.0001 (8)
C6	0.0298 (14)	0.0541 (18)	0.0255 (13)	−0.0149 (13)	−0.0061 (11)	0.0118 (12)
C7	0.0471 (16)	0.0378 (15)	0.0173 (11)	0.0080 (12)	0.0015 (11)	0.0004 (10)
C8	0.0251 (12)	0.0424 (15)	0.0198 (11)	0.0069 (11)	0.0077 (10)	0.0125 (10)
C9	0.0330 (13)	0.0300 (13)	0.0273 (12)	0.0069 (11)	0.0079 (10)	0.0132 (10)
C10	0.0225 (13)	0.0568 (18)	0.0320 (13)	0.0130 (12)	0.0073 (11)	0.0167 (12)
C21	0.0201 (11)	0.0285 (12)	0.0207 (10)	0.0026 (9)	0.0075 (9)	0.0040 (9)
C23	0.0430 (16)	0.0575 (19)	0.0407 (15)	0.0219 (14)	0.0232 (13)	−0.0007 (14)
C24	0.0346 (15)	0.0467 (16)	0.0480 (16)	0.0167 (13)	0.0229 (13)	0.0256 (13)
C25	0.0232 (13)	0.0520 (17)	0.0382 (14)	0.0023 (12)	0.0039 (11)	0.0032 (13)
C111	0.0208 (11)	0.0183 (10)	0.0200 (10)	0.0021 (8)	0.0113 (9)	0.0017 (8)
C112	0.0246 (12)	0.0196 (11)	0.0228 (10)	−0.0008 (9)	0.0117 (9)	−0.0018 (9)
C113	0.0295 (13)	0.0291 (12)	0.0204 (11)	0.0002 (10)	0.0066 (10)	−0.0013 (9)
C114	0.0347 (14)	0.0311 (13)	0.0225 (11)	0.0050 (11)	0.0121 (10)	0.0076 (10)
C115	0.0314 (13)	0.0252 (12)	0.0326 (13)	−0.0023 (10)	0.0158 (11)	0.0065 (10)
C116	0.0230 (12)	0.0228 (11)	0.0263 (11)	−0.0027 (9)	0.0087 (9)	0.0010 (9)
C121	0.0207 (11)	0.0182 (10)	0.0231 (10)	−0.0025 (9)	0.0087 (9)	0.0006 (8)
C122	0.0241 (12)	0.0250 (12)	0.0246 (11)	−0.0012 (9)	0.0096 (9)	0.0002 (9)
C123	0.0314 (13)	0.0277 (13)	0.0399 (14)	0.0026 (10)	0.0189 (12)	0.0000 (11)
C124	0.0249 (13)	0.0313 (14)	0.0527 (16)	0.0046 (11)	0.0150 (12)	0.0068 (12)
C125	0.0236 (13)	0.0340 (14)	0.0396 (14)	−0.0050 (11)	0.0020 (11)	0.0021 (11)
C126	0.0264 (12)	0.0258 (12)	0.0264 (12)	−0.0066 (10)	0.0064 (10)	−0.0026 (9)
C100	0.0264 (13)	0.0414 (15)	0.0296 (13)	0.0052 (11)	0.0044 (11)	0.0017 (11)
Cl1	0.0362 (4)	0.0370 (4)	0.0614 (5)	−0.0056 (3)	0.0022 (3)	−0.0025 (3)
Cl2	0.0818 (6)	0.0558 (5)	0.0758 (6)	0.0302 (5)	0.0536 (5)	0.0199 (4)
Cl3	0.0528 (5)	0.1143 (8)	0.0300 (4)	−0.0006 (5)	0.0042 (3)	0.0028 (4)
I1	0.02343 (9)	0.03225 (10)	0.03755 (10)	0.00095 (6)	0.00995 (7)	−0.00385 (7)

Fe1—C2	2.017 (2)	C21—H21A	0.9900
Fe1—C1	2.017 (2)	C21—H21B	0.9900
Fe1—C8	2.027 (2)	C23—H23A	0.9800
Fe1—C7	2.030 (2)	C23—H23B	0.9800
Fe1—C5	2.035 (2)	C23—H23C	0.9800
Fe1—C9	2.036 (2)	C24—H24A	0.9800
Fe1—C3	2.039 (2)	C24—H24B	0.9800
Fe1—C10	2.053 (3)	C24—H24C	0.9800
Fe1—C6	2.056 (3)	C25—H25A	0.9800
Fe1—C4	2.056 (2)	C25—H25B	0.9800
P1—C1	1.792 (2)	C25—H25C	0.9800
P1—C111	1.814 (2)	C111—C112	1.385 (3)
P1—C121	1.818 (2)	C111—C116	1.389 (3)
P1—S1	1.9524 (7)	C112—C113	1.386 (3)
N1—C24	1.492 (3)	C112—H112	0.9500
N1—C23	1.495 (3)	C113—C114	1.380 (3)
N1—C25	1.497 (3)	C113—H113	0.9500
N1—C21	1.527 (3)	C114—C115	1.375 (4)
C1—C5	1.435 (3)	C114—H114	0.9500
C1—C2	1.453 (3)	C115—C116	1.385 (3)
C2—C3	1.424 (3)	C115—H115	0.9500
C2—C21	1.490 (3)	C116—H116	0.9500
C3—C4	1.403 (3)	C121—C126	1.388 (3)
C3—H3	0.9500	C121—C122	1.395 (3)
C4—C5	1.414 (3)	C122—C123	1.382 (3)
C4—H4	0.9500	C122—H122	0.9500
C5—H5	0.9500	C123—C124	1.383 (4)
C6—C10	1.405 (4)	C123—H123	0.9500
C6—C7	1.417 (4)	C124—C125	1.377 (4)
C6—H6	0.9500	C124—H124	0.9500
C7—C8	1.412 (4)	C125—C126	1.390 (3)
C7—H7	0.9500	C125—H125	0.9500
C8—C9	1.406 (3)	C126—H126	0.9500
C8—H8	0.9500	C100—Cl2	1.745 (3)
C9—C10	1.404 (4)	C100—Cl1	1.752 (3)
C9—H9	0.9500	C100—Cl3	1.753 (3)
C10—H10	0.9500	C100—H100	1.0000
C2—Fe1—C1	42.23 (8)	Fe1—C6—H6	126.7
C2—Fe1—C8	114.24 (9)	C8—C7—C6	108.0 (2)
C1—Fe1—C8	149.55 (9)	C8—C7—Fe1	69.50 (14)
C2—Fe1—C7	108.25 (10)	C6—C7—Fe1	70.69 (15)
C1—Fe1—C7	118.22 (10)	C8—C7—H7	126.0
C8—Fe1—C7	40.74 (11)	C6—C7—H7	126.0
C2—Fe1—C5	69.81 (9)	Fe1—C7—H7	125.4
C1—Fe1—C5	41.49 (8)	C9—C8—C7	107.7 (2)
C8—Fe1—C5	166.33 (10)	C9—C8—Fe1	70.09 (13)
C7—Fe1—C5	152.30 (10)	C7—C8—Fe1	69.76 (13)
C2—Fe1—C9	146.24 (9)	C9—C8—H8	126.2
C1—Fe1—C9	169.62 (9)	C7—C8—H8	126.2
C8—Fe1—C9	40.51 (10)	Fe1—C8—H8	125.6
C7—Fe1—C9	68.06 (11)	C10—C9—C8	108.3 (2)
C5—Fe1—C9	129.32 (10)	C10—C9—Fe1	70.58 (14)
C2—Fe1—C3	41.11 (9)	C8—C9—Fe1	69.41 (13)
C1—Fe1—C3	69.65 (9)	C10—C9—H9	125.8
C8—Fe1—C3	105.52 (10)	C8—C9—H9	125.8
C7—Fe1—C3	129.23 (11)	Fe1—C9—H9	125.8
C5—Fe1—C3	68.38 (9)	C9—C10—C6	108.3 (2)
C9—Fe1—C3	113.61 (10)	C9—C10—Fe1	69.25 (14)
C2—Fe1—C10	171.76 (11)	C6—C10—Fe1	70.12 (15)
C1—Fe1—C10	132.36 (10)	C9—C10—H10	125.8
C8—Fe1—C10	67.91 (10)	C6—C10—H10	125.8
C7—Fe1—C10	67.79 (11)	Fe1—C10—H10	126.4
C5—Fe1—C10	110.07 (10)	C2—C21—N1	115.32 (18)
C9—Fe1—C10	40.17 (10)	C2—C21—H21A	108.4
C3—Fe1—C10	147.00 (11)	N1—C21—H21A	108.4
C2—Fe1—C6	132.44 (11)	C2—C21—H21B	108.4
C1—Fe1—C6	111.10 (10)	N1—C21—H21B	108.4
C8—Fe1—C6	68.21 (10)	H21A—C21—H21B	107.5
C7—Fe1—C6	40.57 (12)	N1—C23—H23A	109.5
C5—Fe1—C6	119.62 (10)	N1—C23—H23B	109.5
C9—Fe1—C6	67.65 (11)	H23A—C23—H23B	109.5
C3—Fe1—C6	169.41 (11)	N1—C23—H23C	109.5
C10—Fe1—C6	39.98 (12)	H23A—C23—H23C	109.5
C2—Fe1—C4	68.76 (9)	H23B—C23—H23C	109.5
C1—Fe1—C4	69.09 (9)	N1—C24—H24A	109.5
C8—Fe1—C4	127.30 (10)	N1—C24—H24B	109.5
C7—Fe1—C4	166.46 (11)	H24A—C24—H24B	109.5
C5—Fe1—C4	40.42 (9)	N1—C24—H24C	109.5
C9—Fe1—C4	106.63 (10)	H24A—C24—H24C	109.5
C3—Fe1—C4	40.07 (9)	H24B—C24—H24C	109.5
C10—Fe1—C4	116.83 (11)	N1—C25—H25A	109.5
C6—Fe1—C4	150.50 (11)	N1—C25—H25B	109.5
C1—P1—C111	105.46 (10)	H25A—C25—H25B	109.5
C1—P1—C121	106.77 (10)	N1—C25—H25C	109.5
C111—P1—C121	101.86 (9)	H25A—C25—H25C	109.5
C1—P1—S1	115.51 (7)	H25B—C25—H25C	109.5
C111—P1—S1	113.33 (7)	C112—C111—C116	120.0 (2)
C121—P1—S1	112.72 (8)	C112—C111—P1	122.49 (16)
C24—N1—C23	109.6 (2)	C116—C111—P1	117.47 (17)
C24—N1—C25	108.6 (2)	C111—C112—C113	119.9 (2)
C23—N1—C25	108.7 (2)	C111—C112—H112	120.1
C24—N1—C21	110.85 (18)	C113—C112—H112	120.1
C23—N1—C21	107.32 (19)	C114—C113—C112	119.9 (2)
C25—N1—C21	111.69 (19)	C114—C113—H113	120.1
C5—C1—C2	106.79 (18)	C112—C113—H113	120.1
C5—C1—P1	123.78 (16)	C115—C114—C113	120.5 (2)
C2—C1—P1	129.43 (16)	C115—C114—H114	119.7
C5—C1—Fe1	69.95 (12)	C113—C114—H114	119.7
C2—C1—Fe1	68.88 (11)	C114—C115—C116	120.0 (2)
P1—C1—Fe1	125.51 (11)	C114—C115—H115	120.0
C3—C2—C1	107.25 (19)	C116—C115—H115	120.0
C3—C2—C21	122.72 (19)	C115—C116—C111	119.8 (2)
C1—C2—C21	129.7 (2)	C115—C116—H116	120.1
C3—C2—Fe1	70.31 (13)	C111—C116—H116	120.1
C1—C2—Fe1	68.89 (12)	C126—C121—C122	119.6 (2)
C21—C2—Fe1	121.12 (15)	C126—C121—P1	120.34 (17)
C4—C3—C2	108.9 (2)	C122—C121—P1	120.05 (17)
C4—C3—Fe1	70.62 (13)	C123—C122—C121	120.1 (2)
C2—C3—Fe1	68.59 (12)	C123—C122—H122	120.0
C4—C3—H3	125.6	C121—C122—H122	120.0
C2—C3—H3	125.6	C122—C123—C124	120.2 (2)
Fe1—C3—H3	126.8	C122—C123—H123	119.9
C3—C4—C5	108.8 (2)	C124—C123—H123	119.9
C3—C4—Fe1	69.31 (13)	C125—C124—C123	119.9 (2)
C5—C4—Fe1	68.99 (12)	C125—C124—H124	120.0
C3—C4—H4	125.6	C123—C124—H124	120.0
C5—C4—H4	125.6	C124—C125—C126	120.5 (2)
Fe1—C4—H4	127.7	C124—C125—H125	119.8
C4—C5—C1	108.33 (19)	C126—C125—H125	119.8
C4—C5—Fe1	70.59 (12)	C121—C126—C125	119.7 (2)
C1—C5—Fe1	68.56 (11)	C121—C126—H126	120.1
C4—C5—H5	125.8	C125—C126—H126	120.1
C1—C5—H5	125.8	Cl2—C100—Cl1	109.90 (14)
Fe1—C5—H5	126.6	Cl2—C100—Cl3	109.62 (14)
C10—C6—C7	107.6 (2)	Cl1—C100—Cl3	110.86 (15)
C10—C6—Fe1	69.89 (15)	Cl2—C100—H100	108.8
C7—C6—Fe1	68.74 (15)	Cl1—C100—H100	108.8
C10—C6—H6	126.2	Cl3—C100—H100	108.8
C7—C6—H6	126.2

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24C···I1	0.98	3.05	4.001 (3)	163
C100—H100···I1	1.00	2.93	3.810 (3)	147

Reference	C2—C21	C21—N1	N1···Cp	C21···Cp	Ang
This study	1.490 (3)	1.527 (3)	1.182 (2)	-0.128 (2)	83.2 (2)
ASAZIE	1.476	1.530	1.253	-0.096	87.49
BUBCOQ	1.505	1.520	1.256	-0.106	90.0
BUBCUW(1)	1.518	1.531	1.260	-0.095	84.38
BUBCUW(2)	1.494	1.525	1.311	-0.048	87.72
DEHHUU	1.482	1.524	1.220	-0.111	90.0
EDUQUP	1.493	1.525	1.294	-0.072	88.68
HABDUL(1)	1.493	1.520	1.167	-0.147	87.20
HABDUL(2)	1.467	1.472	1.270	-0.033	85.45
HABFAT(1)	1.460	1.530	1.233	-0.125	86.58
HABFAT(2)	1.478	1.540	1.125	-0.167	84.17
HABFAT(3)	1.499	1.526	1.309	-0.063	88.73
HIZFOM(1)	1.471	1.519	1.327	-0.029	81.08
HIZFOM(2)	1.447	1.525	1.425	-0.032	90.0
HIZFOM(3)	1.432	1.515	1.393	-0.042	83.97
HIZFOM(4)	1.336	1.529	1.335	-0.007	90.0
IBIROB(1)	1.493	1.529	1.197	-0.142	88.83
IBIROB(2)	1.470	1.537	1.324	-0.060	82.55
IGEPUG(1)	1.519	1.520	1.248	-0.066	77.69
IGEPUG(2)	1.522	1.523	0.999	-0.274	85.92
IGEPUG(3)	1.514	1.533	1.914	-0.426	81.02
IGEPUG(4)	1.516	1.533	1.152	-0.163	83.23
IGEQAN(1)	1.462	1.533	1.251	-0.106	82.66
IGEQAN(2)	1.481	1.543	1.216	-0.123	87.22
IKONOL	1.485	1.522	1.223	-0.100	84.09
IKONOL01	1.484	1.514	1.223	-0.097	90.0
IKONUR	1.495	1.526	1.177	-0.134	86.93
IKUZOD(1)	1.493	1.530	1.272	-0.073	80.32
IKUZOD(2)	1.487	1.528	1.316	-0.050	82.74
IKUZUJ(1)	1.484	1.535	1.290	-0.072	88.63
IKUZUJ(2)	1.489	1.537	1.256	-0.094	87.41
IQUCIG	1.485	1.528	1.263	-0.083	79.62
JUHXEP	1.471	1.516	1.283	-0.066	88.29
JUJDOH	1.482	1.536	1.330	-0.056	88.54
JUJDOH01	1.488	1.510	1.327	-0.033	87.68
JUJFEZ	1.485	1.530	1.225	-0.111	88.50
LEJHIR	1.488	1.521	1.129	-0.141	76.82
LEJHOX(1)	1.502	1.523	1.200	-0.120	83.12
LEJHOX(2)	1.484	1.526	1.203	-0.127	86.84
LIFWUS(1)	1.509	1.536	1.127	-0.166	78.64
LIFWUS(2)	1.485	1.544	1.101	-0.127	69.81
LIFXAZ	1.494	1.525	1.125	-0.129	70.44
NAGHOU	1.501	1.527	1.256	-0.060	77.63
NAGHUA(1)	1.489	1.526	1.235	-0.097	79.70
NAGHUA(2)	1.495	1.528	1.182	-0.129	79.44
NATZEO	1.459	1.549	1.295	-0.074	89.24
NEYSIT	1.486	1.525	1.256	-0.090	86.76
SAZWIA	1.472	1.530	1.188	-0.119	80.76
WASGED(1)	1.489	1.533	1.181	-0.150	88.52
WASGED(2)	1.488	1.523	1.239	-0.101	88.53
WASGED(3)	1.479	1.518	1.241	-0.093	88.22
XAJNIF(1)	1.481	1.519	1.318	-0.054	87.91
XAJNIF(2)	1.488	1.532	1.325	-0.049	87.05
XEQKIN	1.497	1.531	1.378	-0.012	84.17
YOVGOF	1.488	1.524	1.265	-0.057	75.89

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24C⋯I1	0.98	3.05	4.001 (3)	163
C100—H100⋯I1	1.00	2.93	3.810 (3)	147