Dichlorido[(1,2,3,3a,8b-η)-2,4-di­methyl­cyclo­penta­[b]indol­yl)(η5-penta­methyl­cyclo­penta­dien­yl)zirconium(IV)

Medvedev, M.G.; Ryabov, A.N.; Uborsky, D.V.; Kononovich, D.S.; Izmer, V.V.; Voskoboynikov, A.Z.

doi:10.1107/S2414314616014085

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 9| September 2016| x161408

doi:10.1107/S2414314616014085

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Dichlorido[(1,2,3,3a,8b-η)-2,4-dimethylcyclopenta[b]indolyl)(η⁵-pentamethylcyclopentadienyl)zirconium(IV)

Michael G. Medvedev,^a ^* Alexey N. Ryabov,^b Dmitry V. Uborsky,^b Dmitry S. Kononovich,^b Vyatcheslav V. Izmer ^b and Alexander Z. Voskoboynikov ^b

^aX-ray Structural Laboratory, A.N. Nesmeyanov Institute of Organoelement, Compounds, Vavilova St. 28, GSP-1, Moscow 119991, V-334, Russian Federation, and ^bDepartment of Chemistry, Lomonosov Moscow State University 1/3 Leninskie Gory, GSP-1, Moscow 119991, Russian Federation
^*Correspondence e-mail: medvedev.m.g@gmail.com

Edited by K. Fejfarova, Institute of Biotechnology CAS, Czech Republic (Received 4 July 2016; accepted 3 September 2016; online 9 September 2016)

In the structure of the title compound, [Zn(C₁₃H₁₂N)(C₁₀H₁₅)Cl₂], the dihedral angle between the planes of rings coordinating to Zr is 51.6 (2)°. The Cl—Zr—Cl angle is 97.52 (4)°. The crystal structure is stabilized by H⋯Cl and C—H⋯π interactions.

Keywords: crystal structure; zirconium; organozirconium compounds.

CCDC reference: 1502439

Structure description

A view of the title molecule is given on Fig. 1. The chlorine ligands form intramolecular C—H⋯Cl hydrogen bonds (Table 1). The crystal structure is stabilized by C—H⋯π interactions.

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C6–C11 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cl1ⁱ	1.0	2.72	3.684 (5)	162
C10—H10⋯Cl2ⁱⁱ	0.95	2.77	3.699 (5)	166
C22—H22C⋯Cl1	0.98	2.67	3.158 (5)	111
C22—H22A⋯Cg4ⁱⁱⁱ	0.98	2.57	3.487 (5)	156
Symmetry codes: (i) -x+1, -y+1, z; (ii) y, -x+1, -z+1; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 1
The structure of the title compound with displacement ellipsoids at the 50% probability level.

Synthesis and crystallization

The title complex was obtained via treatment of (C₅Me₅)ZrCl₃ (Ryabov et al., 2002 ) with the lithium salt of 2,4-dimethyl-1,4-dihydrocyclopenta[b]indole (van Baar et al., 2003 ) in THF followed by crystallization of the crude product from toluene. Single crystals suitable for X-ray crystal structure analysis were grown from a toluene–hexanes solution at −30°C.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Zn(C₁₃H₁₂N)(C₁₀H₁₅)Cl₂]
M_r	479.57
Crystal system, space group	Tetragonal, P $[\overline{4}]$ 2₁c
Temperature (K)	100
a, c (Å)	15.9363 (8), 16.8801 (8)
V (Å³)	4287.0 (5)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.77
Crystal size (mm)	0.25 × 0.2 × 0.2

Data collection
Diffractometer	Bruker SMART CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001 )
T_min, T_max	0.759, 0.925
No. of measured, independent and observed [I > 2σ(I)] reflections	86055, 5707, 5264
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.096, 1.11
No. of reflections	5707
No. of parameters	251
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.25, −0.38
Absolute structure	Flack x determined using 2285 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013 )
Absolute structure parameter	−0.056 (13)
Computer programs: SMART and SAINT (Bruker, 2001), SHELXS (Sheldrick, 2008 ), SHELXL (Sheldrick, 2015 ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1502439

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616014085/ff4008sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616014085/ff4008Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616014085/ff4008Isup3.mol

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Dichlorido[(1,2,3,3a,8b-η)-2,4-dimethylcyclopenta[b]indolyl)(η⁵-pentamethylcyclopentadienyl]zirconium(IV) top

Crystal data top

[Zn(C₁₃H₁₂N)(C₁₀H₁₅)Cl₂]	D_x = 1.486 Mg m⁻³
M_r = 479.57	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42₁c	Cell parameters from 1024 reflections
a = 15.9363 (8) Å	θ = 2.8–28.9°
c = 16.8801 (8) Å	µ = 0.77 mm⁻¹
V = 4287.0 (5) Å³	T = 100 K
Z = 8	Prism, yellow
F(000) = 1968	0.25 × 0.2 × 0.2 mm

Data collection top

Bruker SMART CCD area detector diffractometer	5264 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
phi and ω scans	θ_max = 29.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −21→21
T_min = 0.759, T_max = 0.925	k = −21→21
86055 measured reflections	l = −23→23
5707 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.042	w = 1/[σ²(F_o²) + (0.040P)² + 7.P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.096	(Δ/σ)_max < 0.001
S = 1.11	Δρ_max = 1.25 e Å⁻³
5707 reflections	Δρ_min = −0.38 e Å⁻³
251 parameters	Absolute structure: Flack x determined using 2285 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.056 (13)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Zr1	0.65206 (2)	0.33633 (2)	0.77455 (2)	0.02065 (10)
Cl1	0.64847 (7)	0.47013 (7)	0.84549 (7)	0.0319 (2)
Cl2	0.65603 (7)	0.39342 (7)	0.64001 (7)	0.0297 (2)
N1	0.4764 (2)	0.3176 (2)	0.6413 (3)	0.0273 (8)
C1	0.4985 (3)	0.3110 (3)	0.7191 (3)	0.0279 (9)
C2	0.4924 (3)	0.3562 (3)	0.7901 (3)	0.0338 (11)
H2	0.4627	0.4110	0.7973	0.041*
C3	0.5219 (3)	0.3034 (4)	0.8516 (3)	0.0362 (12)
C4	0.5521 (3)	0.2274 (3)	0.8176 (3)	0.0279 (10)
H4	0.5667	0.1752	0.8474	0.033*
C5	0.5391 (3)	0.2331 (3)	0.7334 (3)	0.0238 (9)
C6	0.5416 (3)	0.1902 (3)	0.6576 (3)	0.0242 (9)
C7	0.5689 (3)	0.1122 (3)	0.6303 (3)	0.0263 (9)
H7	0.5931	0.0730	0.6660	0.032*
C8	0.5604 (3)	0.0922 (3)	0.5505 (3)	0.0291 (10)
H8	0.5798	0.0394	0.5318	0.035*
C9	0.5237 (3)	0.1489 (4)	0.4974 (3)	0.0310 (10)
H9	0.5183	0.1339	0.4432	0.037*
C10	0.4951 (3)	0.2267 (3)	0.5229 (3)	0.0298 (10)
H10	0.4710	0.2655	0.4867	0.036*
C11	0.5027 (3)	0.2461 (3)	0.6024 (3)	0.0258 (9)
C12	0.5167 (4)	0.3213 (4)	0.9390 (3)	0.0475 (15)
H12A	0.4582	0.3169	0.9565	0.071*
H12B	0.5375	0.3781	0.9495	0.071*
H12C	0.5510	0.2806	0.9680	0.071*
C13	0.4404 (3)	0.3916 (3)	0.6035 (4)	0.0394 (13)
H13A	0.4255	0.4330	0.6441	0.059*
H13B	0.3901	0.3755	0.5739	0.059*
H13C	0.4816	0.4161	0.5671	0.059*
C14	0.7468 (3)	0.2111 (3)	0.7950 (3)	0.0245 (9)
C15	0.7796 (3)	0.2544 (3)	0.7291 (3)	0.0240 (8)
C16	0.8101 (3)	0.3336 (3)	0.7566 (3)	0.0265 (9)
C17	0.7955 (3)	0.3379 (3)	0.8390 (3)	0.0227 (8)
C18	0.7547 (3)	0.2631 (3)	0.8630 (3)	0.0247 (9)
C19	0.7246 (3)	0.1194 (3)	0.7945 (3)	0.0313 (10)
H19B	0.7736	0.0866	0.7780	0.047*
H19C	0.6784	0.1098	0.7572	0.047*
H19A	0.7073	0.1021	0.8477	0.047*
C20	0.7866 (3)	0.2202 (3)	0.6466 (3)	0.0292 (10)
H20A	0.8277	0.1745	0.6458	0.044*
H20B	0.8048	0.2648	0.6106	0.044*
H20C	0.7318	0.1988	0.6295	0.044*
C21	0.8562 (3)	0.3978 (3)	0.7079 (3)	0.0327 (11)
H21B	0.9166	0.3932	0.7179	0.049*
H21C	0.8369	0.4541	0.7224	0.049*
H21A	0.8451	0.3879	0.6516	0.049*
C22	0.8289 (3)	0.4052 (3)	0.8927 (3)	0.0335 (11)
H22A	0.8902	0.4010	0.8955	0.050*
H22B	0.8052	0.3981	0.9459	0.050*
H22C	0.8132	0.4604	0.8719	0.050*
C23	0.7349 (4)	0.2407 (3)	0.9467 (3)	0.0341 (11)
H23A	0.7870	0.2283	0.9752	0.051*
H23B	0.6983	0.1913	0.9476	0.051*
H23C	0.7063	0.2879	0.9723	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zr1	0.02017 (18)	0.01997 (18)	0.02183 (17)	0.00016 (14)	0.00149 (16)	0.00073 (16)
Cl1	0.0272 (5)	0.0237 (5)	0.0448 (6)	0.0029 (4)	−0.0035 (5)	−0.0081 (4)
Cl2	0.0245 (5)	0.0343 (5)	0.0303 (5)	−0.0008 (5)	−0.0015 (5)	0.0120 (4)
N1	0.0210 (17)	0.0251 (18)	0.036 (2)	0.0016 (14)	−0.0022 (16)	0.0037 (16)
C1	0.0195 (19)	0.026 (2)	0.038 (3)	0.0002 (15)	−0.001 (2)	−0.003 (2)
C2	0.0191 (19)	0.036 (3)	0.046 (3)	−0.0020 (18)	0.0064 (18)	−0.009 (2)
C3	0.025 (2)	0.055 (3)	0.028 (2)	−0.009 (2)	0.012 (2)	−0.012 (2)
C4	0.029 (2)	0.029 (2)	0.026 (2)	−0.0101 (19)	0.0053 (18)	0.0029 (19)
C5	0.025 (2)	0.0193 (18)	0.027 (2)	−0.0078 (16)	0.0036 (18)	−0.0006 (17)
C6	0.020 (2)	0.025 (2)	0.027 (2)	−0.0019 (16)	−0.0019 (17)	0.0013 (17)
C7	0.028 (2)	0.023 (2)	0.028 (2)	−0.0005 (18)	−0.0034 (18)	−0.0005 (18)
C8	0.026 (2)	0.033 (2)	0.029 (2)	−0.0013 (18)	0.0008 (18)	−0.0036 (19)
C9	0.026 (2)	0.042 (3)	0.025 (2)	−0.008 (2)	−0.0008 (17)	0.000 (2)
C10	0.026 (2)	0.032 (2)	0.032 (2)	−0.0043 (18)	−0.0061 (19)	0.009 (2)
C11	0.022 (2)	0.025 (2)	0.031 (2)	−0.0026 (17)	−0.0013 (18)	0.0053 (18)
C12	0.039 (3)	0.065 (4)	0.038 (3)	−0.014 (3)	0.013 (2)	−0.014 (3)
C13	0.029 (3)	0.029 (3)	0.060 (4)	0.004 (2)	−0.011 (3)	0.005 (2)
C14	0.025 (2)	0.022 (2)	0.027 (2)	0.0073 (17)	−0.0012 (17)	0.0012 (17)
C15	0.0222 (19)	0.030 (2)	0.020 (2)	0.0079 (16)	−0.0002 (18)	−0.0013 (19)
C16	0.0164 (17)	0.029 (2)	0.034 (2)	0.0052 (17)	0.0001 (16)	0.0033 (19)
C17	0.0199 (18)	0.021 (2)	0.028 (2)	0.0010 (16)	−0.0052 (15)	−0.0031 (17)
C18	0.027 (2)	0.025 (2)	0.023 (2)	0.0048 (17)	−0.0022 (17)	0.0015 (17)
C19	0.038 (3)	0.023 (2)	0.033 (3)	0.0018 (19)	−0.004 (2)	−0.0025 (18)
C20	0.032 (2)	0.037 (3)	0.018 (2)	0.010 (2)	0.0025 (18)	−0.0015 (19)
C21	0.026 (2)	0.028 (2)	0.045 (3)	0.0010 (18)	0.004 (2)	0.0073 (19)
C22	0.029 (2)	0.028 (2)	0.043 (3)	0.0016 (19)	−0.009 (2)	−0.009 (2)
C23	0.049 (3)	0.031 (2)	0.023 (2)	0.007 (2)	0.002 (2)	0.0031 (19)

Geometric parameters (Å, º) top

Zr1—Cl1	2.4463 (12)	C3—C12	1.505 (7)
Zr1—Cl2	2.4473 (12)	C4—C5	1.439 (6)
Zr1—C1	2.651 (4)	C5—C6	1.451 (7)
Zr1—C2	2.578 (5)	C6—C7	1.394 (6)
Zr1—C3	2.504 (5)	C6—C11	1.430 (6)
Zr1—C4	2.466 (5)	C7—C8	1.391 (7)
Zr1—C5	2.535 (4)	C8—C9	1.401 (7)
Zr1—C14	2.525 (4)	C9—C10	1.389 (8)
Zr1—C15	2.534 (4)	C10—C11	1.383 (7)
Zr1—C16	2.538 (4)	C14—C15	1.409 (7)
Zr1—C17	2.532 (4)	C14—C18	1.421 (7)
Zr1—C18	2.504 (4)	C14—C19	1.504 (6)
N1—C1	1.364 (7)	C15—C16	1.429 (7)
N1—C11	1.381 (6)	C15—C20	1.501 (6)
N1—C13	1.459 (6)	C16—C17	1.413 (6)
C1—C2	1.402 (7)	C16—C21	1.504 (6)
C1—C5	1.420 (6)	C17—C18	1.418 (6)
C2—C3	1.418 (8)	C17—C22	1.501 (6)
C3—C4	1.424 (7)	C18—C23	1.491 (7)

Cl1—Zr1—Cl2	97.52 (4)	C1—N1—C13	125.8 (4)
Cl1—Zr1—C1	106.50 (11)	C11—N1—C13	125.4 (4)
Cl1—Zr1—C2	79.62 (12)	N1—C1—Zr1	124.5 (3)
Cl1—Zr1—C3	84.79 (13)	N1—C1—C2	139.9 (5)
Cl1—Zr1—C4	117.03 (12)	N1—C1—C5	110.4 (4)
Cl1—Zr1—C5	133.10 (11)	C2—C1—Zr1	71.6 (3)
Cl1—Zr1—C14	129.47 (11)	C2—C1—C5	109.7 (5)
Cl1—Zr1—C15	128.01 (11)	C5—C1—Zr1	69.7 (2)
Cl1—Zr1—C16	95.56 (11)	C1—C2—Zr1	77.3 (3)
Cl1—Zr1—C17	78.57 (10)	C1—C2—C3	107.3 (4)
Cl1—Zr1—C18	97.46 (11)	C3—C2—Zr1	70.9 (3)
Cl2—Zr1—C1	75.69 (12)	C2—C3—Zr1	76.7 (3)
Cl2—Zr1—C2	94.25 (13)	C2—C3—C4	108.8 (4)
Cl2—Zr1—C3	125.56 (14)	C2—C3—C12	125.9 (5)
Cl2—Zr1—C4	123.48 (12)	C4—C3—Zr1	71.9 (3)
Cl2—Zr1—C5	90.29 (12)	C4—C3—C12	125.2 (6)
Cl2—Zr1—C14	113.90 (11)	C12—C3—Zr1	121.0 (4)
Cl2—Zr1—C15	83.69 (11)	C3—C4—Zr1	74.8 (3)
Cl2—Zr1—C16	82.53 (11)	C3—C4—C5	107.2 (4)
Cl2—Zr1—C17	111.83 (11)	C5—C4—Zr1	75.9 (3)
Cl2—Zr1—C18	135.23 (11)	C1—C5—Zr1	78.7 (3)
C2—Zr1—C1	31.06 (15)	C1—C5—C4	106.7 (4)
C3—Zr1—C1	52.18 (17)	C1—C5—C6	106.0 (4)
C3—Zr1—C2	32.36 (18)	C4—C5—Zr1	70.7 (3)
C3—Zr1—C5	54.44 (16)	C4—C5—C6	146.8 (5)
C3—Zr1—C14	104.96 (18)	C6—C5—Zr1	121.9 (3)
C3—Zr1—C15	135.51 (18)	C7—C6—C5	136.0 (4)
C3—Zr1—C16	151.72 (17)	C7—C6—C11	118.4 (4)
C3—Zr1—C17	121.77 (16)	C11—C6—C5	105.6 (4)
C3—Zr1—C18	97.67 (18)	C8—C7—C6	119.6 (5)
C4—Zr1—C1	53.15 (16)	C7—C8—C9	120.8 (5)
C4—Zr1—C2	54.47 (17)	C10—C9—C8	121.0 (5)
C4—Zr1—C3	33.29 (17)	C11—C10—C9	118.1 (5)
C4—Zr1—C5	33.41 (14)	N1—C11—C6	109.6 (4)
C4—Zr1—C14	77.85 (16)	N1—C11—C10	128.3 (4)
C4—Zr1—C15	104.16 (16)	C10—C11—C6	122.1 (5)
C4—Zr1—C16	131.63 (16)	C15—C14—Zr1	74.2 (2)
C4—Zr1—C17	117.64 (16)	C15—C14—C18	108.6 (4)
C4—Zr1—C18	85.31 (16)	C15—C14—C19	123.9 (4)
C5—Zr1—C1	31.69 (14)	C18—C14—Zr1	72.8 (2)
C5—Zr1—C2	53.63 (15)	C18—C14—C19	126.3 (4)
C5—Zr1—C16	131.34 (15)	C19—C14—Zr1	128.8 (3)
C14—Zr1—C1	118.66 (15)	C14—C15—Zr1	73.5 (3)
C14—Zr1—C2	132.32 (17)	C14—C15—C16	107.6 (4)
C14—Zr1—C5	87.08 (15)	C14—C15—C20	125.6 (4)
C14—Zr1—C15	32.35 (15)	C16—C15—Zr1	73.8 (2)
C14—Zr1—C16	53.80 (15)	C16—C15—C20	126.6 (4)
C14—Zr1—C17	53.82 (15)	C20—C15—Zr1	121.9 (3)
C15—Zr1—C1	123.72 (15)	C15—C16—Zr1	73.5 (2)
C15—Zr1—C2	152.35 (16)	C15—C16—C21	126.1 (4)
C15—Zr1—C5	98.75 (14)	C17—C16—Zr1	73.6 (2)
C15—Zr1—C16	32.73 (15)	C17—C16—C15	107.9 (4)
C16—Zr1—C1	150.64 (16)	C17—C16—C21	125.8 (4)
C16—Zr1—C2	173.85 (16)	C21—C16—Zr1	122.5 (3)
C17—Zr1—C1	170.66 (15)	C16—C17—Zr1	74.0 (2)
C17—Zr1—C2	147.81 (15)	C16—C17—C18	108.4 (4)
C17—Zr1—C5	139.93 (14)	C16—C17—C22	124.9 (4)
C17—Zr1—C15	53.93 (14)	C18—C17—Zr1	72.6 (2)
C17—Zr1—C16	32.36 (14)	C18—C17—C22	126.2 (4)
C18—Zr1—C1	137.96 (15)	C22—C17—Zr1	125.9 (3)
C18—Zr1—C2	129.92 (17)	C14—C18—Zr1	74.4 (3)
C18—Zr1—C5	108.95 (15)	C14—C18—C23	127.4 (4)
C18—Zr1—C14	32.82 (15)	C17—C18—Zr1	74.7 (2)
C18—Zr1—C15	54.29 (15)	C17—C18—C14	107.5 (4)
C18—Zr1—C16	54.17 (15)	C17—C18—C23	124.7 (4)
C18—Zr1—C17	32.70 (15)	C23—C18—Zr1	122.5 (3)
C1—N1—C11	108.4 (4)

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C6–C11 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl1ⁱ	1.0	2.72	3.684 (5)	162
C10—H10···Cl2ⁱⁱ	0.95	2.77	3.699 (5)	166
C22—H22C···Cl1	0.98	2.67	3.158 (5)	111
C22—H22A···Cg4ⁱⁱⁱ	0.98	2.57	3.487 (5)	156

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

Acknowledgements

This work was supported by the Ministry of Education and Science of the Russian Federation, grant agreement No. 14.613.21.0041 on 11.11.2015 (unique project identifier RFMEFI61315X0041).

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