Literature DB >> 21581115

2-(4-Ferrocenylphen-yl)-4,4,5,5-tetra-methyl-1,3,2-dioxaborolane.

Abstract

In the title compound,, [Fe(C(5)H(5))(C(17)H(20)BO(2))], the two near parallel cyclo-penta-dienyl rings of the ferrocene group are eclipsed. The benzene ring is tilted with respect to the attached cyclo-penta-diene ring by 17.0 (1)° and by 24.2 (1)° with respect to the dioxaborolane ring. The mol-ecules assemble in the crystal via C-H⋯π inter-actions between the cyclo-penta-dienyl H atoms and the benzene and cyclo-penta-dienyl rings of neighbouring mol-ecules.

Entities: CellLine Chemical Disease Gene Species

Year: 2008 PMID： 21581115 PMCID： PMC2959994 DOI： 10.1107/S1600536808035228

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the related tris(4-ferrocenylphenyl)boroxine benzene solvate, see: Makarov et al. (2004 ▶). For other related structures, see: Anderson et al. (2003 ▶); Nyamori & Bala (2008 ▶). For related literature, see: Leclerc et al. (2003 ▶).

Experimental

Crystal data

[Fe(C5H5)(C17H20BO2)] M = 388.08 Monoclinic, a = 12.4439 (3) Å b = 12.9832 (3) Å c = 13.0728 (3) Å β = 117.126 (1)° V = 1879.75 (8) Å3 Z = 4 Mo Kα radiation μ = 0.82 mm−1 T = 89 (2) K 0.37 × 0.37 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.717, T max = 0.849 23134 measured reflections 4442 independent reflections 3984 reflections with I > 2σ(I) R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.031 wR(F 2) = 0.085 S = 1.03 4442 reflections 239 parameters H-atom parameters constrained Δρmax = 0.86 e Å−3 Δρmin = −0.31 e Å−3 Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2008 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035228/hg2435sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035228/hg2435Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Fe(C₅H₅)(C₁₇H₂₀BO₂)]	F₀₀₀ = 816
M_r = 388.08	D_x = 1.371 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9781 reflections
a = 12.4439 (3) Å	θ = 1.8–27.8º
b = 12.9832 (3) Å	µ = 0.82 mm⁻¹
c = 13.0728 (3) Å	T = 89 (2) K
β = 117.126 (1)º	Block, orange
V = 1879.75 (8) Å³	0.37 × 0.37 × 0.2 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4442 independent reflections
Radiation source: fine-focus sealed tube	3984 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.027
T = 89(2) K	θ_max = 27.8º
ω scans	θ_min = 1.8º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)	h = −16→14
T_min = 0.717, T_max = 0.849	k = 0→17
23134 measured reflections	l = 0→17

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)] = 0.031	H-atom parameters constrained
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0491P)² + 1.0943P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4442 reflections	Δρ_max = 0.86 e Å⁻³
239 parameters	Δρ_min = −0.31 e Å⁻³
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 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	U_iso*/U_eq
Fe1	0.244744 (18)	0.661122 (14)	0.209954 (16)	0.01545 (8)
O2	0.36539 (9)	1.21833 (8)	−0.03562 (9)	0.0207 (2)
O1	0.16554 (9)	1.19391 (8)	−0.16076 (9)	0.0195 (2)
C11	0.26427 (12)	0.89643 (10)	0.14427 (11)	0.0157 (3)
C14	0.26540 (13)	1.05937 (10)	0.00034 (12)	0.0167 (3)
C18	0.33635 (13)	1.29767 (11)	−0.12386 (12)	0.0187 (3)
C2	0.16209 (14)	0.52057 (11)	0.16048 (14)	0.0231 (3)
H2	0.1105	0.4901	0.1854	0.028*
C16	0.37235 (12)	0.94523 (10)	0.16343 (12)	0.0178 (3)
H16	0.4447	0.9239	0.2241	0.021*
C7	0.15815 (13)	0.78484 (11)	0.23606 (12)	0.0186 (3)
H7	0.0789	0.8050	0.1895	0.022*
C13	0.15859 (13)	1.00753 (10)	−0.02096 (12)	0.0172 (3)
H13	0.0868	1.0269	−0.0836	0.021*
C8	0.26304 (13)	0.81901 (11)	0.22597 (12)	0.0167 (3)
C9	0.36571 (13)	0.76831 (11)	0.31467 (12)	0.0187 (3)
H9	0.4454	0.7758	0.3281	0.022*
C6	0.19744 (14)	0.71467 (11)	0.33018 (12)	0.0209 (3)
H6	0.1480	0.6811	0.3556	0.025*
B1	0.26500 (15)	1.15783 (11)	−0.06779 (14)	0.0174 (3)
C15	0.37260 (13)	1.02504 (11)	0.09282 (12)	0.0184 (3)
H15	0.4453	1.0564	0.1071	0.022*
C5	0.23381 (15)	0.61510 (11)	0.05503 (13)	0.0243 (3)
H5	0.2370	0.6572	−0.0011	0.029*
C21	0.39377 (14)	1.39832 (11)	−0.06503 (13)	0.0238 (3)
H21A	0.3680	1.4143	−0.0079	0.036*
H21B	0.3695	1.4526	−0.1210	0.036*
H21C	0.4801	1.3916	−0.0290	0.036*
C4	0.33403 (14)	0.56821 (11)	0.14749 (13)	0.0226 (3)
H4	0.4144	0.5745	0.1628	0.027*
C10	0.32509 (14)	0.70475 (11)	0.37867 (12)	0.0208 (3)
H10	0.3735	0.6639	0.4413	0.025*
C12	0.15769 (12)	0.92783 (10)	0.04947 (12)	0.0169 (3)
H12	0.0854	0.8949	0.0335	0.020*
C17	0.19486 (13)	1.29760 (11)	−0.18488 (13)	0.0201 (3)
C22	0.39120 (14)	1.26270 (11)	−0.20117 (14)	0.0235 (3)
H22A	0.4761	1.2510	−0.1555	0.035*
H22B	0.3790	1.3150	−0.2573	0.035*
H22C	0.3530	1.2000	−0.2395	0.035*
C3	0.29014 (14)	0.50988 (11)	0.21282 (14)	0.0228 (3)
H3	0.3369	0.4715	0.2783	0.027*
C20	0.14060 (15)	1.37292 (13)	−0.13159 (16)	0.0294 (3)
H20A	0.0554	1.3605	−0.1625	0.044*
H20B	0.1539	1.4422	−0.1489	0.044*
H20C	0.1783	1.3635	−0.0498	0.044*
C19	0.13736 (16)	1.31085 (15)	−0.31429 (14)	0.0312 (4)
H19A	0.1653	1.2574	−0.3471	0.047*
H19B	0.1593	1.3768	−0.3324	0.047*
H19C	0.0511	1.3068	−0.3453	0.047*
C1	0.12727 (14)	0.58627 (12)	0.06311 (13)	0.0249 (3)
H1	0.0489	0.6067	0.0136	0.030*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.02072 (12)	0.00975 (11)	0.01600 (12)	−0.00098 (7)	0.00849 (9)	0.00033 (7)
O2	0.0219 (5)	0.0155 (5)	0.0231 (5)	−0.0012 (4)	0.0087 (4)	0.0059 (4)
O1	0.0234 (5)	0.0134 (5)	0.0205 (5)	−0.0019 (4)	0.0090 (4)	0.0031 (4)
C11	0.0225 (6)	0.0095 (5)	0.0171 (6)	−0.0009 (5)	0.0106 (5)	−0.0026 (5)
C14	0.0228 (7)	0.0119 (6)	0.0174 (6)	0.0003 (5)	0.0110 (5)	−0.0002 (5)
C18	0.0234 (7)	0.0130 (6)	0.0206 (7)	0.0000 (5)	0.0107 (6)	0.0037 (5)
C2	0.0296 (8)	0.0134 (6)	0.0292 (8)	−0.0063 (6)	0.0159 (6)	−0.0055 (6)
C16	0.0196 (6)	0.0135 (6)	0.0192 (6)	0.0003 (5)	0.0078 (5)	−0.0001 (5)
C7	0.0243 (7)	0.0137 (6)	0.0202 (7)	−0.0002 (5)	0.0122 (6)	−0.0005 (5)
C13	0.0214 (7)	0.0144 (6)	0.0155 (6)	0.0007 (5)	0.0080 (5)	−0.0011 (5)
C8	0.0235 (7)	0.0105 (6)	0.0170 (6)	−0.0017 (5)	0.0099 (5)	−0.0018 (5)
C9	0.0232 (7)	0.0140 (6)	0.0176 (6)	−0.0024 (5)	0.0081 (6)	−0.0015 (5)
C6	0.0310 (8)	0.0147 (6)	0.0214 (7)	−0.0024 (5)	0.0158 (6)	0.0000 (5)
B1	0.0228 (8)	0.0131 (7)	0.0182 (7)	−0.0004 (5)	0.0111 (6)	−0.0004 (5)
C15	0.0207 (6)	0.0142 (6)	0.0215 (7)	−0.0014 (5)	0.0106 (6)	−0.0008 (5)
C5	0.0386 (9)	0.0156 (7)	0.0207 (7)	−0.0018 (6)	0.0153 (6)	−0.0020 (5)
C21	0.0284 (7)	0.0160 (7)	0.0263 (7)	−0.0033 (6)	0.0118 (6)	0.0005 (6)
C4	0.0291 (7)	0.0154 (6)	0.0273 (7)	−0.0018 (6)	0.0165 (6)	−0.0046 (6)
C10	0.0305 (8)	0.0149 (6)	0.0153 (6)	−0.0012 (5)	0.0090 (6)	0.0011 (5)
C12	0.0210 (6)	0.0127 (6)	0.0185 (6)	−0.0031 (5)	0.0102 (5)	−0.0032 (5)
C17	0.0246 (7)	0.0128 (6)	0.0241 (7)	0.0002 (5)	0.0122 (6)	0.0038 (5)
C22	0.0303 (8)	0.0157 (6)	0.0308 (8)	−0.0003 (6)	0.0193 (7)	0.0017 (6)
C3	0.0316 (8)	0.0103 (6)	0.0272 (7)	0.0015 (5)	0.0140 (6)	0.0007 (5)
C20	0.0302 (8)	0.0184 (7)	0.0438 (10)	0.0026 (6)	0.0205 (8)	−0.0005 (7)
C19	0.0293 (8)	0.0348 (9)	0.0256 (8)	0.0004 (7)	0.0090 (7)	0.0131 (7)
C1	0.0274 (8)	0.0194 (7)	0.0216 (7)	−0.0019 (6)	0.0057 (6)	−0.0056 (6)

Fe1—C6	2.0357 (14)	C13—C12	1.3885 (19)
Fe1—C3	2.0388 (14)	C13—H13	0.9300
Fe1—C10	2.0431 (14)	C8—C9	1.435 (2)
Fe1—C4	2.0454 (15)	C9—C10	1.4220 (19)
Fe1—C7	2.0477 (14)	C9—H9	0.9300
Fe1—C2	2.0492 (14)	C6—C10	1.422 (2)
Fe1—C9	2.0488 (14)	C6—H6	0.9300
Fe1—C1	2.0512 (15)	C15—H15	0.9300
Fe1—C5	2.0558 (15)	C5—C4	1.419 (2)
Fe1—C8	2.0626 (14)	C5—C1	1.427 (2)
O2—B1	1.3695 (19)	C5—H5	0.9300
O2—C18	1.4636 (16)	C21—H21A	0.9600
O1—B1	1.3626 (19)	C21—H21B	0.9600
O1—C17	1.4663 (16)	C21—H21C	0.9600
C11—C12	1.4007 (19)	C4—C3	1.424 (2)
C11—C16	1.4020 (19)	C4—H4	0.9300
C11—C8	1.4718 (18)	C10—H10	0.9300
C14—C13	1.3998 (19)	C12—H12	0.9300
C14—C15	1.403 (2)	C17—C19	1.516 (2)
C14—B1	1.557 (2)	C17—C20	1.525 (2)
C18—C21	1.519 (2)	C22—H22A	0.9600
C18—C22	1.524 (2)	C22—H22B	0.9600
C18—C17	1.567 (2)	C22—H22C	0.9600
C2—C3	1.426 (2)	C3—H3	0.9300
C2—C1	1.426 (2)	C20—H20A	0.9600
C2—H2	0.9300	C20—H20B	0.9600
C16—C15	1.3887 (19)	C20—H20C	0.9600
C16—H16	0.9300	C19—H19A	0.9600
C7—C6	1.426 (2)	C19—H19B	0.9600
C7—C8	1.4405 (19)	C19—H19C	0.9600
C7—H7	0.9300	C1—H1	0.9300

C6—Fe1—C3	119.34 (6)	C11—C8—Fe1	129.97 (9)
C6—Fe1—C10	40.82 (6)	C10—C9—C8	108.51 (13)
C3—Fe1—C10	104.60 (6)	C10—C9—Fe1	69.45 (8)
C6—Fe1—C4	155.59 (6)	C8—C9—Fe1	70.09 (8)
C3—Fe1—C4	40.80 (6)	C10—C9—H9	125.7
C10—Fe1—C4	120.46 (6)	C8—C9—H9	125.7
C6—Fe1—C7	40.89 (6)	Fe1—C9—H9	126.3
C3—Fe1—C7	156.19 (6)	C10—C6—C7	108.43 (12)
C10—Fe1—C7	68.79 (6)	C10—C6—Fe1	69.87 (8)
C4—Fe1—C7	162.19 (6)	C7—C6—Fe1	70.01 (8)
C6—Fe1—C2	105.52 (6)	C10—C6—H6	125.8
C3—Fe1—C2	40.82 (6)	C7—C6—H6	125.8
C10—Fe1—C2	121.05 (6)	Fe1—C6—H6	125.9
C4—Fe1—C2	68.57 (6)	O1—B1—O2	114.03 (12)
C7—Fe1—C2	121.64 (6)	O1—B1—C14	123.86 (13)
C6—Fe1—C9	68.60 (6)	O2—B1—C14	122.06 (13)
C3—Fe1—C9	121.93 (6)	C16—C15—C14	121.35 (13)
C10—Fe1—C9	40.67 (5)	C16—C15—H15	119.3
C4—Fe1—C9	107.46 (6)	C14—C15—H15	119.3
C7—Fe1—C9	68.77 (6)	C4—C5—C1	108.05 (13)
C2—Fe1—C9	157.80 (6)	C4—C5—Fe1	69.37 (8)
C6—Fe1—C1	123.42 (6)	C1—C5—Fe1	69.50 (9)
C3—Fe1—C1	68.54 (6)	C4—C5—H5	126.0
C10—Fe1—C1	158.56 (6)	C1—C5—H5	126.0
C4—Fe1—C1	68.41 (6)	Fe1—C5—H5	126.7
C7—Fe1—C1	108.84 (6)	C18—C21—H21A	109.5
C2—Fe1—C1	40.69 (6)	C18—C21—H21B	109.5
C9—Fe1—C1	160.07 (6)	H21A—C21—H21B	109.5
C6—Fe1—C5	161.33 (7)	C18—C21—H21C	109.5
C3—Fe1—C5	68.38 (6)	H21A—C21—H21C	109.5
C10—Fe1—C5	157.54 (7)	H21B—C21—H21C	109.5
C4—Fe1—C5	40.47 (6)	C5—C4—C3	108.11 (13)
C7—Fe1—C5	126.07 (6)	C5—C4—Fe1	70.16 (9)
C2—Fe1—C5	68.40 (6)	C3—C4—Fe1	69.36 (8)
C9—Fe1—C5	123.65 (6)	C5—C4—H4	125.9
C1—Fe1—C5	40.67 (6)	C3—C4—H4	125.9
C6—Fe1—C8	68.88 (5)	Fe1—C4—H4	126.1
C3—Fe1—C8	159.79 (6)	C9—C10—C6	108.03 (12)
C10—Fe1—C8	68.77 (5)	C9—C10—Fe1	69.88 (8)
C4—Fe1—C8	124.87 (6)	C6—C10—Fe1	69.31 (8)
C7—Fe1—C8	41.03 (5)	C9—C10—H10	126.0
C2—Fe1—C8	158.96 (6)	C6—C10—H10	126.0
C9—Fe1—C8	40.85 (6)	Fe1—C10—H10	126.4
C1—Fe1—C8	124.36 (6)	C13—C12—C11	120.85 (13)
C5—Fe1—C8	110.09 (6)	C13—C12—H12	119.6
B1—O2—C18	107.39 (11)	C11—C12—H12	119.6
B1—O1—C17	107.07 (11)	O1—C17—C19	107.88 (12)
C12—C11—C16	118.08 (12)	O1—C17—C20	106.56 (12)
C12—C11—C8	121.46 (12)	C19—C17—C20	110.78 (14)
C16—C11—C8	120.36 (13)	O1—C17—C18	102.89 (11)
C13—C14—C15	117.52 (12)	C19—C17—C18	114.64 (12)
C13—C14—B1	121.73 (13)	C20—C17—C18	113.31 (12)
C15—C14—B1	120.50 (13)	C18—C22—H22A	109.5
O2—C18—C21	108.44 (11)	C18—C22—H22B	109.5
O2—C18—C22	106.79 (11)	H22A—C22—H22B	109.5
C21—C18—C22	110.03 (12)	C18—C22—H22C	109.5
O2—C18—C17	102.54 (10)	H22A—C22—H22C	109.5
C21—C18—C17	114.71 (12)	H22B—C22—H22C	109.5
C22—C18—C17	113.65 (12)	C4—C3—C2	108.11 (13)
C3—C2—C1	107.76 (13)	C4—C3—Fe1	69.85 (8)
C3—C2—Fe1	69.20 (8)	C2—C3—Fe1	69.98 (8)
C1—C2—Fe1	69.73 (8)	C4—C3—H3	125.9
C3—C2—H2	126.1	C2—C3—H3	125.9
C1—C2—H2	126.1	Fe1—C3—H3	125.8
Fe1—C2—H2	126.5	C17—C20—H20A	109.5
C15—C16—C11	120.74 (13)	C17—C20—H20B	109.5
C15—C16—H16	119.6	H20A—C20—H20B	109.5
C11—C16—H16	119.6	C17—C20—H20C	109.5
C6—C7—C8	107.89 (13)	H20A—C20—H20C	109.5
C6—C7—Fe1	69.10 (8)	H20B—C20—H20C	109.5
C8—C7—Fe1	70.04 (8)	C17—C19—H19A	109.5
C6—C7—H7	126.1	C17—C19—H19B	109.5
C8—C7—H7	126.1	H19A—C19—H19B	109.5
Fe1—C7—H7	126.4	C17—C19—H19C	109.5
C12—C13—C14	121.36 (13)	H19A—C19—H19C	109.5
C12—C13—H13	119.3	H19B—C19—H19C	109.5
C14—C13—H13	119.3	C2—C1—C5	107.97 (14)
C9—C8—C7	107.14 (12)	C2—C1—Fe1	69.58 (8)
C9—C8—C11	126.85 (12)	C5—C1—Fe1	69.84 (9)
C7—C8—C11	125.90 (13)	C2—C1—H1	126.0
C9—C8—Fe1	69.06 (8)	C5—C1—H1	126.0
C7—C8—Fe1	68.93 (8)	Fe1—C1—H1	126.1

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···C12ⁱ	0.93	2.86	3.6302 (19)	141
C5—H5···C6ⁱⁱ	0.93	2.62	3.538 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯C12ⁱ	0.93	2.86	3.6302 (19)	141
C5—H5⋯C6ⁱⁱ	0.93	2.62	3.538 (2)	168

Symmetry codes: (i) ; (ii) .

3 in total

2-(4-Ferrocenylphen-yl)-4,4,5,5-tetra-methyl-1,3,2-dioxaborolane.

Related literature

Experimental

Crystal data

Data collection

Refinement

1. A short history of SHELX.

2. 1-(4-Bromo-phen-yl)ferrocene.

3. Ethyl and isopropyl 4-ferrocenyl-benzoate.