3,3,6,6-Tetra­phenyl-trans-tricyclo­[3.1.0.0^2,4]hexane

The title compound, C₃₀H₂₄, was produced serendipitously whilst investigating the reactions of 3,3-diphenyl­cyclo­propane with low-valent metal substrates. There are only a small number of crystal structure determinations of products from metal-catalysed (2 + 2)-cyclo­additions of cyclo­propenes. The product here is the centrosymmetric trans isomer.

Key indicators

• Single-crystal X-ray study
• T = 85 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.048
• wR factor = 0.120
• Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.02
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1995).

3,3,6,6-Tetraphenyl-trans-tricyclo[3.1.0.0^2,4]hexane

Crystal data

C30H24	F(000) = 408
Mr = 384.49	Dx = 1.214 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.1918 (5) Å	Cell parameters from 4253 reflections
b = 18.4683 (12) Å	θ = 2.2–25.7°
c = 7.0314 (4) Å	µ = 0.07 mm^−1
β = 98.709 (1)°	T = 85 K
V = 1051.51 (11) Å^3	Plate, colourless
Z = 2	0.28 × 0.22 × 0.12 mm

Data collection

Siemens SMART CCD diffractometer	1994 independent reflections
Radiation source: fine-focus sealed tube	1630 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 25.7°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.924, Tmax = 0.970	k = 0→22
5914 measured reflections	l = 0→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	All H-atom parameters refined
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0494P)^2 + 0.4478P] where P = (Fo^2 + 2Fc^2)/3
1994 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3558 (2)	−0.01306 (9)	0.1602 (2)	0.0261 (4)
C2	0.5385 (2)	−0.01928 (9)	0.1434 (2)	0.0253 (4)
H2	0.610 (2)	−0.0506 (10)	0.224 (3)	0.028 (5)*
C3	0.4051 (2)	−0.04069 (10)	−0.0258 (2)	0.0248 (4)
H3	0.372 (2)	−0.0886 (11)	−0.072 (2)	0.028 (5)*
C4	0.2798 (2)	0.06096 (9)	0.1638 (2)	0.0250 (4)
C5	0.3470 (2)	0.11191 (10)	0.2990 (2)	0.0283 (4)
H5	0.448 (2)	0.0994 (10)	0.395 (3)	0.026 (4)*
C6	0.2796 (2)	0.18099 (10)	0.3005 (3)	0.0318 (4)
H6	0.327 (2)	0.2160 (11)	0.392 (3)	0.036 (5)*
C7	0.1433 (2)	0.19987 (10)	0.1668 (3)	0.0302 (4)
H7	0.094 (2)	0.2485 (11)	0.171 (3)	0.032 (5)*
C8	0.0751 (2)	0.14923 (10)	0.0325 (3)	0.0308 (4)
H8	−0.020 (2)	0.1610 (11)	−0.062 (3)	0.038 (5)*
C9	0.1430 (2)	0.08025 (9)	0.0307 (2)	0.0279 (4)
H9	0.092 (2)	0.0426 (10)	−0.068 (3)	0.033 (5)*
C10	0.2955 (2)	−0.07043 (9)	0.2874 (2)	0.0263 (4)
C11	0.1857 (2)	−0.05273 (10)	0.4123 (3)	0.0311 (4)
H11	0.147 (3)	−0.0014 (11)	0.420 (3)	0.039 (5)*
C12	0.1330 (2)	−0.10495 (11)	0.5320 (3)	0.0354 (5)
H12	0.056 (3)	−0.0911 (12)	0.620 (3)	0.046 (6)*
C13	0.1893 (2)	−0.17561 (10)	0.5292 (3)	0.0328 (4)
H13	0.149 (2)	−0.2112 (10)	0.610 (3)	0.032 (5)*
C14	0.2994 (2)	−0.19413 (10)	0.4069 (3)	0.0325 (4)
H14	0.341 (2)	−0.2439 (11)	0.405 (3)	0.033 (5)*
C15	0.3527 (2)	−0.14161 (10)	0.2856 (2)	0.0291 (4)
H15	0.432 (2)	−0.1563 (10)	0.204 (3)	0.034 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0261 (9)	0.0286 (9)	0.0220 (8)	−0.0020 (7)	−0.0013 (7)	0.0005 (7)
C2	0.0234 (8)	0.0294 (9)	0.0208 (8)	−0.0009 (7)	−0.0035 (6)	0.0013 (7)
C3	0.0237 (8)	0.0285 (9)	0.0205 (8)	−0.0031 (7)	−0.0025 (7)	0.0001 (7)
C4	0.0242 (8)	0.0290 (9)	0.0221 (8)	−0.0027 (7)	0.0040 (7)	0.0035 (7)
C5	0.0261 (9)	0.0340 (10)	0.0234 (9)	−0.0010 (7)	−0.0005 (7)	0.0002 (7)
C6	0.0320 (10)	0.0322 (10)	0.0305 (10)	−0.0035 (8)	0.0029 (8)	−0.0054 (8)
C7	0.0289 (9)	0.0275 (9)	0.0348 (10)	0.0018 (7)	0.0068 (8)	0.0045 (8)
C8	0.0254 (9)	0.0347 (10)	0.0312 (10)	0.0008 (7)	0.0004 (7)	0.0069 (8)
C9	0.0258 (9)	0.0309 (10)	0.0261 (9)	−0.0038 (7)	0.0012 (7)	0.0021 (7)
C10	0.0232 (8)	0.0299 (9)	0.0224 (8)	−0.0040 (7)	−0.0075 (7)	0.0017 (7)
C11	0.0284 (9)	0.0354 (11)	0.0276 (9)	−0.0012 (8)	−0.0018 (7)	0.0037 (8)
C12	0.0312 (10)	0.0431 (11)	0.0303 (10)	−0.0031 (8)	−0.0005 (8)	0.0072 (8)
C13	0.0304 (9)	0.0353 (10)	0.0296 (10)	−0.0099 (8)	−0.0052 (8)	0.0090 (8)
C14	0.0328 (9)	0.0299 (10)	0.0309 (10)	−0.0051 (8)	−0.0080 (8)	0.0006 (8)
C15	0.0270 (9)	0.0330 (10)	0.0244 (9)	−0.0023 (7)	−0.0049 (7)	−0.0012 (7)

Geometric parameters (Å, º)

C1—C4	1.504 (2)	C7—H7	0.99 (2)
C1—C3	1.514 (2)	C8—C9	1.391 (3)
C1—C10	1.517 (2)	C8—H8	0.97 (2)
C1—C2	1.523 (2)	C9—H9	1.027 (19)
C2—C3^i	1.496 (2)	C10—C11	1.388 (3)
C2—C3	1.540 (2)	C10—C15	1.396 (2)
C2—H2	0.946 (19)	C11—C12	1.391 (3)
C3—C2^i	1.496 (2)	C11—H11	1.00 (2)
C3—H3	0.966 (19)	C12—C13	1.385 (3)
C4—C5	1.391 (2)	C12—H12	0.99 (2)
C4—C9	1.393 (2)	C13—C14	1.380 (3)
C5—C6	1.391 (2)	C13—H13	0.959 (19)
C5—H5	1.010 (18)	C14—C15	1.404 (3)
C6—C7	1.391 (2)	C14—H14	0.98 (2)
C6—H6	0.95 (2)	C15—H15	0.97 (2)
C7—C8	1.385 (3)
C4—C1—C3	119.10 (14)	C8—C7—C6	119.42 (17)
C4—C1—C10	116.87 (14)	C8—C7—H7	120.6 (11)
C3—C1—C10	115.29 (14)	C6—C7—H7	119.9 (11)
C4—C1—C2	118.95 (14)	C7—C8—C9	120.26 (17)
C3—C1—C2	60.93 (11)	C7—C8—H8	121.0 (12)
C10—C1—C2	113.88 (14)	C9—C8—H8	118.7 (12)
C3^i—C2—C1	112.10 (14)	C8—C9—C4	120.68 (16)
C3^i—C2—C3	90.32 (13)	C8—C9—H9	120.3 (11)
C1—C2—C3	59.23 (11)	C4—C9—H9	119.0 (11)
C3^i—C2—H2	124.8 (11)	C11—C10—C15	118.55 (16)
C1—C2—H2	121.4 (11)	C11—C10—C1	120.60 (15)
C3—C2—H2	127.4 (11)	C15—C10—C1	120.82 (16)
C2^i—C3—C1	111.89 (14)	C10—C11—C12	120.65 (18)
C2^i—C3—C2	89.68 (13)	C10—C11—H11	120.0 (11)
C1—C3—C2	59.83 (11)	C12—C11—H11	119.3 (11)
C2^i—C3—H3	126.0 (10)	C13—C12—C11	120.68 (19)
C1—C3—H3	119.9 (10)	C13—C12—H12	120.0 (13)
C2—C3—H3	128.5 (11)	C11—C12—H12	119.3 (13)
C5—C4—C9	118.77 (16)	C14—C13—C12	119.51 (17)
C5—C4—C1	120.29 (15)	C14—C13—H13	121.0 (11)
C9—C4—C1	120.93 (15)	C12—C13—H13	119.5 (11)
C6—C5—C4	120.61 (16)	C13—C14—C15	120.00 (18)
C6—C5—H5	119.3 (10)	C13—C14—H14	120.4 (11)
C4—C5—H5	120.0 (10)	C15—C14—H14	119.6 (11)
C5—C6—C7	120.26 (17)	C10—C15—C14	120.60 (17)
C5—C6—H6	120.4 (12)	C10—C15—H15	121.6 (11)
C7—C6—H6	119.3 (12)	C14—C15—H15	117.8 (11)

Symmetry code: (i) −x+1, −y, −z.