(Ferrocenylmethyl)trimethylammonium triiodide

Blake, A.J.; Caltagirone, C.; Lippolis, V.; Schröder, M.; Wilson, C.

doi:10.1107/S1600536803026084

(Ferrocenylmethyl)trimethylammonium triiodide

A. J. Blake, C. Caltagirone, V. Lippolis, M. Schröder and C. Wilson

The salt (ferrocenylmethyl)trimethylammonium iodide, [Fe(C₅H₅)(C₉H₁₅N)]I, is used in an established procedure to attach ferrocenylmethyl frameworks to secondary amines. The title salt, [Fe(C₅H₅)(C₉H₁₅N)]I₃, obtained by diffusion of Et₂O vapour into a CH₂Cl₂ solution containing equimolar [Fe(C₅H₅)(C₉H₁₅N)]I and I₂, shows the expected cation balanced by an asymmetric but isolated triiodide counteranion [I-I = 3.0006 (4) and 2.8728 (4) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803026084/om6194sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803026084/om6194Isup2.hkl Contains datablock I

CCDC reference: 231806

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
R factor = 0.026
wR factor = 0.062
Data-to-parameter ratio = 25.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.80

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT and SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: enCIFer (CCDC, 2003) and PLATON (Spek, 2003).

(Ferrocenylmethyl)trimethylammonium triiodide top

Crystal data top

[Fe(C₅H₅)(C₉H₁₅N)]I₃	F(000) = 1184
M_r = 638.86	D_x = 2.228 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7671 reflections
a = 11.6959 (9) Å	θ = 2.3–27.6°
b = 10.6136 (9) Å	µ = 5.64 mm⁻¹
c = 15.3474 (12) Å	T = 150 K
β = 91.638 (2)°	Block, red
V = 1904.4 (3) Å³	0.50 × 0.36 × 0.30 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4393 independent reflections
Radiation source: normal-focus sealed tube	3925 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 27.6°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→14
T_min = 0.064, T_max = 0.180	k = −13→12
13480 measured reflections	l = −20→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.062	w = 1/[σ²(F_o²) + (0.029P)² + 2.356P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
4393 reflections	Δρ_max = 1.08 e Å⁻³
173 parameters	Δρ_min = −1.18 e Å⁻³
113 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00106 (8)

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Fe	0.57586 (4)	0.41067 (4)	0.25079 (2)	0.01770 (10)
C1	0.4474 (3)	0.3846 (3)	0.16064 (17)	0.0184 (6)
C2	0.5574 (3)	0.3775 (3)	0.12134 (18)	0.0235 (6)
H2	0.5886	0.3037	0.0892	0.028*
C3	0.6139 (3)	0.4952 (3)	0.1362 (2)	0.0287 (7)
H3	0.6922	0.5178	0.1170	0.034*
C4	0.5408 (3)	0.5734 (3)	0.1841 (2)	0.0315 (7)
H4	0.5592	0.6605	0.2050	0.038*
C5	0.4381 (3)	0.5074 (3)	0.1987 (2)	0.0243 (6)
H5	0.3716	0.5396	0.2317	0.029*
C6	0.5635 (3)	0.2764 (4)	0.3459 (2)	0.0351 (8)
H6	0.5019	0.2116	0.3500	0.042*
C7	0.6673 (3)	0.2630 (4)	0.3009 (2)	0.0371 (8)
H7	0.6908	0.1867	0.2676	0.044*
C8	0.7307 (3)	0.3744 (4)	0.3096 (2)	0.0387 (9)
H8	0.8074	0.3913	0.2848	0.046*
C9	0.6666 (3)	0.4582 (4)	0.3613 (2)	0.0403 (9)
H9	0.6899	0.5454	0.3790	0.048*
C10	0.5626 (3)	0.3968 (4)	0.3829 (2)	0.0384 (9)
H10	0.5003	0.4333	0.4184	0.046*
N12	0.2867 (2)	0.2681 (3)	0.08344 (16)	0.0237 (6)
C11	0.3607 (3)	0.2830 (3)	0.16649 (18)	0.0217 (6)
H11A	0.3105	0.3013	0.2158	0.026*
H11B	0.4002	0.2023	0.1791	0.026*
C13	0.1944 (3)	0.1737 (3)	0.1018 (2)	0.0315 (8)
H13A	0.1455	0.1623	0.0494	0.047*
H13B	0.1481	0.2044	0.1496	0.047*
H13C	0.2294	0.0929	0.1182	0.047*
C14	0.3576 (3)	0.2202 (4)	0.0107 (2)	0.0369 (8)
H14A	0.3095	0.2109	−0.0422	0.055*
H14B	0.3904	0.1382	0.0269	0.055*
H14C	0.4194	0.2800	−0.0001	0.055*
C15	0.2323 (3)	0.3907 (3)	0.0578 (2)	0.0311 (8)
H15A	0.1853	0.3790	0.0046	0.047*
H15B	0.2919	0.4533	0.0474	0.047*
H15C	0.1839	0.4200	0.1049	0.047*
I1	0.57558 (2)	0.08364 (2)	−0.202225 (17)	0.03604 (8)
I2	0.733082 (18)	0.20712 (2)	−0.070191 (13)	0.02773 (7)
I3	0.88581 (2)	0.31936 (3)	0.057543 (16)	0.03910 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe	0.0160 (2)	0.0243 (2)	0.01252 (18)	0.00239 (16)	−0.00494 (15)	−0.00021 (15)
C1	0.0202 (14)	0.0222 (14)	0.0125 (12)	0.0032 (11)	−0.0050 (10)	0.0003 (11)
C2	0.0229 (15)	0.0344 (17)	0.0131 (12)	0.0061 (13)	−0.0025 (11)	−0.0013 (12)
C3	0.0256 (16)	0.0373 (19)	0.0231 (14)	−0.0037 (14)	−0.0033 (12)	0.0122 (13)
C4	0.0332 (18)	0.0236 (16)	0.0369 (17)	0.0002 (14)	−0.0115 (15)	0.0073 (13)
C5	0.0225 (15)	0.0246 (16)	0.0254 (14)	0.0071 (12)	−0.0079 (12)	−0.0042 (12)
C6	0.0342 (18)	0.046 (2)	0.0243 (15)	−0.0063 (16)	−0.0121 (14)	0.0163 (14)
C7	0.039 (2)	0.043 (2)	0.0280 (16)	0.0157 (16)	−0.0131 (15)	0.0068 (15)
C8	0.0179 (15)	0.071 (3)	0.0267 (16)	0.0015 (16)	−0.0113 (13)	0.0154 (17)
C9	0.046 (2)	0.051 (2)	0.0229 (15)	−0.0084 (18)	−0.0211 (15)	−0.0014 (15)
C10	0.0369 (19)	0.063 (2)	0.0146 (13)	0.0048 (18)	−0.0078 (13)	0.0006 (15)
N12	0.0231 (13)	0.0286 (14)	0.0187 (12)	−0.0020 (11)	−0.0121 (10)	0.0032 (10)
C11	0.0234 (15)	0.0271 (16)	0.0140 (12)	0.0001 (12)	−0.0095 (11)	0.0021 (11)
C13	0.0296 (18)	0.0293 (17)	0.0346 (17)	−0.0066 (14)	−0.0161 (14)	0.0049 (14)
C14	0.043 (2)	0.048 (2)	0.0186 (15)	−0.0024 (18)	−0.0062 (14)	−0.0087 (14)
C15	0.0320 (18)	0.0308 (18)	0.0296 (16)	0.0018 (14)	−0.0149 (14)	0.0120 (14)
I1	0.02726 (13)	0.03188 (13)	0.04844 (15)	0.00596 (9)	−0.00824 (10)	0.00393 (10)
I2	0.02294 (11)	0.02951 (12)	0.03092 (12)	0.00938 (8)	0.00389 (8)	0.00381 (8)
I3	0.02922 (13)	0.04378 (15)	0.04403 (14)	0.00875 (10)	−0.00385 (10)	−0.00688 (11)

Geometric parameters (Å, º) top

Fe—C1	2.032 (3)	C8—H8	1.0000
Fe—C2	2.023 (3)	C9—C10	1.427 (6)
Fe—C3	2.034 (3)	C9—H9	1.0000
Fe—C4	2.043 (3)	C10—H10	1.0000
Fe—C5	2.053 (3)	C10—C6	1.399 (6)
Fe—C6	2.048 (3)	C1—C11	1.486 (4)
Fe—C7	2.036 (3)	C11—H11A	0.9900
Fe—C8	2.037 (3)	C11—H11B	0.9900
Fe—C9	2.038 (3)	C11—N12	1.528 (3)
Fe—C10	2.044 (3)	N12—C15	1.496 (4)
C1—C2	1.438 (4)	N12—C14	1.499 (4)
C2—C3	1.428 (5)	N12—C13	1.505 (4)
C2—H2	1.0000	C13—H13A	0.9800
C3—C4	1.412 (5)	C13—H13B	0.9800
C3—H3	1.0000	C13—H13C	0.9800
C4—C5	1.415 (5)	C14—H14A	0.9800
C4—H4	1.0000	C14—H14B	0.9800
C5—H5	1.0000	C14—H14C	0.9800
C5—C1	1.433 (4)	C15—H15A	0.9800
C6—C7	1.421 (5)	C15—H15B	0.9800
C6—H6	1.0000	C15—H15C	0.9800
C7—C8	1.400 (6)	I1—I2	3.0006 (4)
C7—H7	1.0000	I2—I3	2.8728 (4)
C8—C9	1.420 (6)

I3···C15ⁱ	3.791 (3)	I1···H13C^iv	3.19
I1···H4ⁱ	3.14	I1···H15Cⁱⁱⁱ	3.25
I1···H8ⁱⁱ	3.15	I2···H2	3.18
I1···H11Aⁱⁱⁱ	3.29	I2···H13C^iv	3.30
I1···H11B^iv	3.07	I3···H3	3.24
I1···H13Bⁱⁱⁱ	3.33	I3···H9^v	3.20

C2—Fe—C1	41.56 (12)	Fe—C4—H4	125.6
C2—Fe—C3	41.22 (14)	C4—C5—C1	108.1 (3)
C1—Fe—C3	69.33 (12)	C4—C5—Fe	69.42 (18)
C2—Fe—C7	106.07 (14)	C1—C5—Fe	68.65 (16)
C1—Fe—C7	121.51 (14)	C4—C5—H5	125.9
C3—Fe—C7	122.72 (15)	C1—C5—H5	125.9
C2—Fe—C8	118.07 (14)	Fe—C5—H5	125.9
C1—Fe—C8	155.05 (15)	C10—C6—C7	107.8 (3)
C3—Fe—C8	104.64 (14)	C10—C6—Fe	69.9 (2)
C7—Fe—C8	40.22 (17)	C7—C6—Fe	69.2 (2)
C2—Fe—C9	153.98 (15)	C10—C6—H6	126.1
C1—Fe—C9	163.23 (15)	C7—C6—H6	126.1
C3—Fe—C9	119.26 (15)	Fe—C6—H6	126.1
C7—Fe—C9	67.72 (16)	C8—C7—C6	109.1 (4)
C8—Fe—C9	40.80 (17)	C8—C7—Fe	69.9 (2)
C2—Fe—C4	68.96 (14)	C6—C7—Fe	70.1 (2)
C1—Fe—C4	68.90 (13)	C8—C7—H7	125.5
C3—Fe—C4	40.52 (15)	C6—C7—H7	125.5
C7—Fe—C4	159.33 (16)	Fe—C7—H7	125.5
C8—Fe—C4	123.00 (16)	C7—C8—C9	107.2 (3)
C9—Fe—C4	107.45 (16)	C7—C8—Fe	69.85 (19)
C2—Fe—C10	162.37 (15)	C9—C8—Fe	69.65 (19)
C1—Fe—C10	126.19 (14)	C7—C8—H8	126.4
C3—Fe—C10	156.07 (16)	C9—C8—H8	126.4
C7—Fe—C10	67.90 (16)	Fe—C8—H8	126.4
C8—Fe—C10	68.80 (15)	C8—C9—C10	108.1 (4)
C9—Fe—C10	40.91 (16)	C8—C9—Fe	69.55 (19)
C4—Fe—C10	122.56 (16)	C10—C9—Fe	69.76 (19)
C2—Fe—C6	124.81 (15)	C8—C9—H9	125.9
C1—Fe—C6	108.95 (13)	C10—C9—H9	125.9
C3—Fe—C6	160.81 (16)	Fe—C9—H9	125.9
C7—Fe—C6	40.72 (15)	C6—C10—C9	107.8 (4)
C8—Fe—C6	68.45 (15)	C6—C10—Fe	70.16 (19)
C9—Fe—C6	67.96 (16)	C9—C10—Fe	69.33 (19)
C4—Fe—C6	158.14 (16)	C6—C10—H10	126.1
C10—Fe—C6	39.99 (16)	C9—C10—H10	126.1
C2—Fe—C5	69.17 (12)	Fe—C10—H10	126.1
C1—Fe—C5	41.08 (12)	C15—N12—C14	109.9 (3)
C3—Fe—C5	68.38 (13)	C15—N12—C13	109.0 (3)
C7—Fe—C5	158.42 (15)	C14—N12—C13	109.2 (3)
C8—Fe—C5	160.89 (16)	C15—N12—C11	110.8 (2)
C9—Fe—C5	125.76 (15)	C14—N12—C11	110.1 (2)
C4—Fe—C5	40.40 (14)	C13—N12—C11	107.8 (2)
C10—Fe—C5	109.96 (14)	C1—C11—N12	113.3 (2)
C6—Fe—C5	123.70 (14)	C1—C11—H11A	108.9
C5—C1—C2	107.4 (3)	N12—C11—H11A	108.9
C5—C1—C11	125.1 (3)	C1—C11—H11B	108.9
C2—C1—C11	127.4 (3)	N12—C11—H11B	108.9
C5—C1—Fe	70.28 (16)	H11A—C11—H11B	107.7
C2—C1—Fe	68.91 (16)	N12—C13—H13A	109.5
C11—C1—Fe	123.41 (19)	N12—C13—H13B	109.5
C3—C2—C1	107.5 (3)	H13A—C13—H13B	109.5
C3—C2—Fe	69.81 (17)	N12—C13—H13C	109.5
C1—C2—Fe	69.54 (15)	H13A—C13—H13C	109.5
C3—C2—H2	126.2	H13B—C13—H13C	109.5
C1—C2—H2	126.2	N12—C14—H14A	109.5
Fe—C2—H2	126.2	N12—C14—H14B	109.5
C4—C3—C2	108.3 (3)	H14A—C14—H14B	109.5
C4—C3—Fe	70.08 (19)	N12—C14—H14C	109.5
C2—C3—Fe	68.97 (17)	H14A—C14—H14C	109.5
C4—C3—H3	125.9	H14B—C14—H14C	109.5
C2—C3—H3	125.9	N12—C15—H15A	109.5
Fe—C3—H3	125.9	N12—C15—H15B	109.5
C3—C4—C5	108.7 (3)	H15A—C15—H15B	109.5
C3—C4—Fe	69.40 (19)	N12—C15—H15C	109.5
C5—C4—Fe	70.18 (18)	H15A—C15—H15C	109.5
C3—C4—H4	125.6	H15B—C15—H15C	109.5
C5—C4—H4	125.6	I1—I2—I3	178.600 (10)

C5—C1—C11—N12	102.1 (3)	C14—N12—C11—C1	67.6 (3)
C2—C1—C11—N12	−81.8 (4)	C13—N12—C11—C1	−173.4 (3)
C15—N12—C11—C1	−54.2 (4)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x+1, −y, −z; (v) −x+3/2, y−1/2, −z+1/2.

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