cis-1,2,2,3-Tetra­phenyl-2,3-dihydro-1H-2-benzosilole

The title compound, C₃₂H₂₆Si, is a benzosilacyclo­pentene in which the silacyclo­pentene ring assumes an envelope conformation, with the Si atom displaced by 0.953 (2) Å from the mean plane of the four C atoms. The Si atom is bonded to two phenyl rings and to two Csp³ atoms in the silacyclo­pentene ring; one phenyl ring is attached to each of these two Csp³ atoms in the cis configuration.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.101
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    Si     -   C16     ..       5.09 su

   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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

cis-1,2,2,3-Tetraphenyl-2,3-dihydro-1H-2-benzosilole

Crystal data

C32H26Si	Z = 2
Mr = 438.62	F(000) = 464
Triclinic, P1	Dx = 1.195 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 9.877 (3) Å	Cell parameters from 25 reflections
b = 10.633 (2) Å	θ = 3.5–25.2°
c = 13.693 (2) Å	µ = 0.96 mm^−1
α = 67.620 (14)°	T = 295 K
β = 84.657 (18)°	Prism, colorless
γ = 66.77 (2)°	0.50 × 0.30 × 0.25 mm
V = 1219.2 (5) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.013
Radiation source: normal-focus sealed tube	θmax = 69.9°, θmin = 3.5°
Graphite monochromator	h = −11→12
non–profiled ω/2θ scans	k = −11→12
7796 measured reflections	l = −12→16
4604 independent reflections	3 standard reflections every 94 reflections
4113 reflections with I > 2σ(I)	intensity decay: 3%

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0506P)^2 + 0.2363P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.035	(Δ/σ)max < 0.001
wR(F^2) = 0.101	Δρmax = 0.23 e Å^−3
S = 1.03	Δρmin = −0.20 e Å^−3
4604 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
299 parameters	Extinction coefficient: 0.0250 (10)
0 restraints

Special details

Experimental. (1): ¹H NMR (300 MHz, CDCl₃, δ, p.p.m.): 3.95 (s, 4H), 7.05–7.26 (m, 14H); ¹³C NMR (75.4 MHz, CDCl₃, δ, p.p.m.): 39.0 (CH₂), 126.0 (CH), 126.6 (CH), 128.4 (CH), 128.8 (CH), 130.6 (CH), 138.9 (C), 140.8 (C).

(3): ¹H NMR (500 MHz, CDCl₃, δ, p.p.m.): 4.36 (s, 2H), 6.71 (d, J = 8 Hz, 2H), 6.93 (t, J = 8 Hz, 2H), 7.05 (m, 6H), 7.13 (m, 5H), 7.25 (m, 4H), 7.42 (bt, J = 7 Hz, 2H), 7.47 (bt, J = 7 Hz, 1H), 7.66 (d, J = 8 Hz, 2H); ¹³C NMR (125.7 MHz, CDCl₃, δ, p.p.m.): 41.59 (CH), 124.82 (CH), 126.88 (CH), 127.07 (CH), 128.20(CH), 128.22 (CH), 128.27 (CH), 128.87 (CH), 129.59 (C), 130.03 (C), 130.49(C), 134.38 (C), 135.05 (CH), 136.36 (CH), 141.83 (C), 144.28 (C)

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 (Ų)

	x	y	z	Uiso*/Ueq
Si	0.43091 (4)	0.68959 (4)	0.73198 (3)	0.04569 (13)
C22	0.27888 (14)	0.86421 (14)	0.64767 (10)	0.0466 (3)
C27	0.16428 (16)	0.95296 (16)	0.69054 (12)	0.0558 (3)
H27	0.1606	0.9231	0.7637	0.067*
C16	0.56546 (14)	0.60922 (14)	0.64593 (11)	0.0485 (3)
C23	0.27846 (16)	0.91449 (15)	0.53762 (11)	0.0528 (3)
H23	0.3526	0.8585	0.5064	0.063*
C24	0.17074 (18)	1.04549 (17)	0.47352 (12)	0.0627 (4)
H24	0.1735	1.0767	0.4003	0.075*
C28	0.25036 (16)	0.50845 (16)	0.80844 (11)	0.0555 (3)
C33	0.10765 (18)	0.60581 (18)	0.76522 (13)	0.0658 (4)
H33	0.0768	0.7049	0.7549	0.079*
C5	0.38919 (17)	0.72624 (16)	0.91117 (11)	0.0571 (4)
C10	0.57759 (16)	0.83369 (16)	0.81243 (11)	0.0535 (3)
C21	0.58560 (19)	0.47552 (16)	0.63999 (14)	0.0641 (4)
H21	0.535	0.4201	0.6838	0.077*
C26	0.05716 (16)	1.08338 (16)	0.62663 (13)	0.0609 (4)
H26	−0.0172	1.1407	0.6569	0.073*
C4	0.30808 (17)	0.64298 (16)	0.91202 (11)	0.0572 (4)
C17	0.64621 (17)	0.68624 (18)	0.57996 (14)	0.0625 (4)
H17	0.637	0.7752	0.5828	0.075*
C15	0.50363 (18)	0.97942 (17)	0.74465 (14)	0.0643 (4)
H15	0.4126	1.0066	0.7119	0.077*
C19	0.7551 (2)	0.50218 (19)	0.50561 (15)	0.0725 (5)
H19	0.8172	0.467	0.4583	0.087*
C1	0.51491 (16)	0.71737 (15)	0.83767 (11)	0.0537 (3)
H1	0.5959	0.6228	0.8745	0.064*
C11	0.71408 (19)	0.7988 (2)	0.85753 (15)	0.0740 (5)
H11	0.7675	0.7023	0.9029	0.089*
C14	0.5618 (2)	1.08499 (18)	0.72472 (14)	0.0679 (4)
H14	0.5095	1.1818	0.6795	0.081*
C25	0.05989 (18)	1.12922 (16)	0.51803 (13)	0.0639 (4)
H25	−0.0132	1.2167	0.4751	0.077*
C32	0.0112 (2)	0.5578 (2)	0.73738 (14)	0.0742 (5)
H32	−0.0838	0.6245	0.7095	0.089*
C3	0.35802 (16)	0.55839 (15)	0.83785 (11)	0.0536 (3)
H3	0.4444	0.4688	0.8742	0.064*
C6	0.3457 (2)	0.8162 (2)	0.96970 (13)	0.0744 (5)
H6	0.3988	0.8716	0.9695	0.089*
C29	0.2910 (2)	0.36132 (18)	0.82231 (14)	0.0687 (4)
H29	0.3848	0.2932	0.8519	0.082*
C20	0.6792 (2)	0.42314 (19)	0.57040 (16)	0.0767 (5)
H20C	0.6906	0.3335	0.5677	0.092*
C8	0.1448 (3)	0.7397 (3)	1.03046 (15)	0.0917 (6)
H8	0.0632	0.7442	1.0709	0.11*
C31	0.0547 (2)	0.4124 (2)	0.75065 (15)	0.0798 (5)
H31	−0.01	0.3806	0.7311	0.096*
C18	0.73960 (19)	0.6336 (2)	0.51045 (15)	0.0730 (5)
H18	0.792	0.6873	0.4669	0.088*
C13	0.6960 (2)	1.0475 (2)	0.77119 (15)	0.0733 (5)
H13	0.7348	1.1186	0.7585	0.088*
C30	0.1947 (2)	0.3142 (2)	0.79299 (17)	0.0824 (5)
H30	0.225	0.2156	0.802	0.099*
C9	0.1865 (2)	0.6493 (2)	0.97282 (12)	0.0727 (5)
H9	0.1334	0.5931	0.9748	0.087*
C7	0.2225 (3)	0.8226 (3)	1.02838 (15)	0.0930 (6)
H7	0.1924	0.8838	1.0667	0.112*
C12	0.7723 (2)	0.9049 (2)	0.83637 (18)	0.0869 (6)
H12	0.8646	0.8785	0.867	0.104*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si	0.0453 (2)	0.03789 (19)	0.0459 (2)	−0.01026 (14)	0.00127 (14)	−0.01339 (15)
C22	0.0462 (7)	0.0397 (6)	0.0490 (7)	−0.0149 (5)	0.0004 (5)	−0.0130 (5)
C27	0.0520 (8)	0.0495 (7)	0.0523 (8)	−0.0120 (6)	0.0039 (6)	−0.0132 (6)
C16	0.0445 (7)	0.0428 (7)	0.0528 (7)	−0.0119 (5)	0.0008 (5)	−0.0173 (6)
C23	0.0577 (8)	0.0456 (7)	0.0508 (7)	−0.0173 (6)	0.0006 (6)	−0.0160 (6)
C24	0.0740 (10)	0.0521 (8)	0.0490 (8)	−0.0209 (7)	−0.0066 (7)	−0.0071 (6)
C28	0.0589 (8)	0.0478 (7)	0.0495 (7)	−0.0209 (6)	0.0080 (6)	−0.0083 (6)
C33	0.0634 (9)	0.0542 (8)	0.0664 (10)	−0.0218 (7)	0.0009 (7)	−0.0094 (7)
C5	0.0621 (8)	0.0528 (8)	0.0394 (7)	−0.0102 (7)	−0.0067 (6)	−0.0103 (6)
C10	0.0553 (8)	0.0491 (7)	0.0534 (8)	−0.0125 (6)	−0.0025 (6)	−0.0231 (6)
C21	0.0721 (10)	0.0463 (8)	0.0734 (10)	−0.0240 (7)	0.0204 (8)	−0.0245 (7)
C26	0.0496 (8)	0.0469 (8)	0.0709 (10)	−0.0087 (6)	0.0039 (7)	−0.0169 (7)
C4	0.0621 (8)	0.0489 (7)	0.0380 (7)	−0.0109 (6)	−0.0014 (6)	−0.0033 (6)
C17	0.0601 (9)	0.0571 (8)	0.0800 (11)	−0.0285 (7)	0.0159 (7)	−0.0325 (8)
C15	0.0613 (9)	0.0514 (8)	0.0739 (10)	−0.0149 (7)	−0.0124 (7)	−0.0207 (7)
C19	0.0688 (10)	0.0645 (10)	0.0729 (11)	−0.0131 (8)	0.0205 (8)	−0.0311 (8)
C1	0.0531 (8)	0.0428 (7)	0.0522 (8)	−0.0072 (6)	−0.0077 (6)	−0.0139 (6)
C11	0.0662 (10)	0.0605 (9)	0.0825 (12)	−0.0148 (8)	−0.0191 (9)	−0.0186 (9)
C14	0.0777 (11)	0.0515 (8)	0.0735 (10)	−0.0219 (8)	−0.0017 (8)	−0.0243 (8)
C25	0.0596 (9)	0.0432 (7)	0.0673 (10)	−0.0107 (6)	−0.0102 (7)	−0.0048 (7)
C32	0.0652 (10)	0.0791 (12)	0.0695 (10)	−0.0348 (9)	0.0038 (8)	−0.0119 (9)
C3	0.0532 (8)	0.0402 (7)	0.0506 (7)	−0.0106 (6)	−0.0010 (6)	−0.0067 (6)
C6	0.0884 (12)	0.0791 (11)	0.0508 (9)	−0.0220 (9)	−0.0030 (8)	−0.0287 (8)
C29	0.0684 (10)	0.0523 (8)	0.0768 (11)	−0.0241 (8)	0.0115 (8)	−0.0163 (8)
C20	0.0919 (13)	0.0531 (9)	0.0872 (12)	−0.0236 (9)	0.0245 (10)	−0.0376 (9)
C8	0.0977 (15)	0.1110 (16)	0.0519 (10)	−0.0323 (13)	0.0255 (10)	−0.0292 (10)
C31	0.0863 (13)	0.0937 (14)	0.0761 (12)	−0.0587 (12)	0.0197 (10)	−0.0279 (10)
C18	0.0650 (10)	0.0756 (11)	0.0819 (12)	−0.0335 (9)	0.0257 (9)	−0.0316 (9)
C13	0.0786 (11)	0.0726 (11)	0.0808 (12)	−0.0364 (9)	0.0038 (9)	−0.0339 (9)
C30	0.0940 (14)	0.0662 (11)	0.0966 (14)	−0.0450 (10)	0.0232 (11)	−0.0300 (10)
C9	0.0802 (11)	0.0723 (10)	0.0468 (8)	−0.0263 (9)	0.0101 (8)	−0.0080 (7)
C7	0.1103 (16)	0.1108 (17)	0.0582 (11)	−0.0319 (14)	0.0175 (10)	−0.0462 (11)
C12	0.0707 (11)	0.0850 (13)	0.1071 (16)	−0.0319 (10)	−0.0177 (11)	−0.0311 (12)

Geometric parameters (Å, º)

Si—C16	1.8611 (15)	C17—H17	0.93
Si—C22	1.8777 (15)	C15—C14	1.383 (2)
Si—C1	1.9007 (15)	C15—H15	0.93
Si—C3	1.9038 (15)	C19—C20	1.364 (3)
C22—C23	1.3938 (19)	C19—C18	1.372 (2)
C22—C27	1.404 (2)	C19—H19	0.93
C27—C26	1.378 (2)	C1—H1	0.98
C27—H27	0.93	C11—C12	1.386 (3)
C16—C21	1.389 (2)	C11—H11	0.93
C16—C17	1.393 (2)	C14—C13	1.366 (2)
C23—C24	1.384 (2)	C14—H14	0.93
C23—H23	0.93	C25—H25	0.93
C24—C25	1.372 (2)	C32—C31	1.373 (3)
C24—H24	0.93	C32—H32	0.93
C28—C29	1.392 (2)	C3—H3	0.98
C28—C33	1.395 (2)	C6—C7	1.388 (3)
C28—C3	1.504 (2)	C6—H6	0.93
C33—C32	1.383 (2)	C29—C30	1.384 (3)
C33—H33	0.93	C29—H29	0.93
C5—C6	1.392 (2)	C20—H20C	0.93
C5—C4	1.406 (2)	C8—C7	1.370 (3)
C5—C1	1.520 (2)	C8—C9	1.386 (3)
C10—C11	1.387 (2)	C8—H8	0.93
C10—C15	1.391 (2)	C31—C30	1.374 (3)
C10—C1	1.507 (2)	C31—H31	0.93
C21—C20	1.381 (2)	C18—H18	0.93
C21—H21	0.93	C13—C12	1.363 (3)
C26—C25	1.379 (2)	C13—H13	0.93
C26—H26	0.93	C30—H30	0.93
C4—C9	1.390 (2)	C9—H9	0.93
C4—C3	1.528 (2)	C7—H7	0.93
C17—C18	1.380 (2)	C12—H12	0.93
C16—Si—C22	109.70 (6)	C10—C1—H1	105.9
C16—Si—C1	115.01 (7)	C5—C1—H1	105.9
C22—Si—C1	111.95 (6)	Si—C1—H1	105.9
C16—Si—C3	115.92 (7)	C12—C11—C10	121.27 (16)
C22—Si—C3	112.55 (6)	C12—C11—H11	119.4
C1—Si—C3	90.68 (7)	C10—C11—H11	119.4
C23—C22—C27	116.69 (12)	C13—C14—C15	120.22 (16)
C23—C22—Si	120.54 (10)	C13—C14—H14	119.9
C27—C22—Si	122.74 (10)	C15—C14—H14	119.9
C26—C27—C22	121.44 (14)	C24—C25—C26	119.82 (14)
C26—C27—H27	119.3	C24—C25—H25	120.1
C22—C27—H27	119.3	C26—C25—H25	120.1
C21—C16—C17	116.86 (13)	C31—C32—C33	120.45 (18)
C21—C16—Si	122.66 (11)	C31—C32—H32	119.8
C17—C16—Si	120.40 (11)	C33—C32—H32	119.8
C24—C23—C22	121.81 (14)	C28—C3—C4	117.49 (13)
C24—C23—H23	119.1	C28—C3—Si	120.72 (10)
C22—C23—H23	119.1	C4—C3—Si	98.12 (9)
C25—C24—C23	120.00 (14)	C28—C3—H3	106.4
C25—C24—H24	120	C4—C3—H3	106.4
C23—C24—H24	120	Si—C3—H3	106.4
C29—C28—C33	117.05 (16)	C7—C6—C5	119.5 (2)
C29—C28—C3	120.66 (14)	C7—C6—H6	120.2
C33—C28—C3	122.28 (14)	C5—C6—H6	120.2
C32—C33—C28	121.30 (16)	C30—C29—C28	121.43 (17)
C32—C33—H33	119.4	C30—C29—H29	119.3
C28—C33—H33	119.4	C28—C29—H29	119.3
C6—C5—C4	119.79 (16)	C19—C20—C21	120.38 (16)
C6—C5—C1	124.81 (16)	C19—C20—H20C	119.8
C4—C5—C1	115.26 (13)	C21—C20—H20C	119.8
C11—C10—C15	116.65 (15)	C7—C8—C9	120.65 (19)
C11—C10—C1	120.53 (14)	C7—C8—H8	119.7
C15—C10—C1	122.82 (13)	C9—C8—H8	119.7
C20—C21—C16	121.40 (15)	C32—C31—C30	119.43 (18)
C20—C21—H21	119.3	C32—C31—H31	120.3
C16—C21—H21	119.3	C30—C31—H31	120.3
C27—C26—C25	120.24 (14)	C19—C18—C17	119.97 (16)
C27—C26—H26	119.9	C19—C18—H18	120
C25—C26—H26	119.9	C17—C18—H18	120
C9—C4—C5	119.66 (16)	C12—C13—C14	119.35 (17)
C9—C4—C3	124.98 (16)	C12—C13—H13	120.3
C5—C4—C3	115.24 (13)	C14—C13—H13	120.3
C18—C17—C16	121.58 (15)	C31—C30—C29	120.33 (18)
C18—C17—H17	119.2	C31—C30—H30	119.8
C16—C17—H17	119.2	C29—C30—H30	119.8
C14—C15—C10	121.75 (15)	C8—C9—C4	119.7 (2)
C14—C15—H15	119.1	C8—C9—H9	120.2
C10—C15—H15	119.1	C4—C9—H9	120.2
C20—C19—C18	119.79 (16)	C8—C7—C6	120.68 (19)
C20—C19—H19	120.1	C8—C7—H7	119.7
C18—C19—H19	120.1	C6—C7—H7	119.7
C10—C1—C5	116.53 (12)	C13—C12—C11	120.75 (17)
C10—C1—Si	122.88 (10)	C13—C12—H12	119.6
C5—C1—Si	98.27 (10)	C11—C12—H12	119.6