2-Phenyl­selanyl-3,5-methano-2H-cyclo­penta­[b]­furan-2-one

The title compound, C₁₄H₁₄O₂Se, crystallizes as separate neutral mol­ecules each consisting of one norbornane moiety bridged through aa Se atom to a phenyl group and covalently bonded to both the C and O atoms of a carboxyl­ate group forming a five-membered ring. It is a useful intermediate in the synthesis of larger organometallic complexes. One mol­ecule of the title compound constitutes the asymmetric unit. The packing of mol­ecules in well defined layers results in a number of C—H...Se `agostic' interactions and weak C—H...O=C hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.023
• wR factor = 0.054
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.79 mm

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.34
           From the CIF: _reflns_number_total               2344
           Count of symmetry unique reflns         1406
           Completeness (_total/calc)            166.71%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       938
           Fraction of Friedel pairs measured     0.667
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL'; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-Phenylselanyl-3,5-methano-2H-cyclopenta[b]furan-2-one

Crystal data

C14H14O2Se	Dx = 1.661 Mg m^−3
Mr = 293.21	Melting point: 376 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4814 reflections
a = 6.2771 (13) Å	θ = 4.3–53.0°
b = 9.792 (2) Å	µ = 3.19 mm^−1
c = 19.073 (4) Å	T = 293 K
V = 1172.4 (4) Å^3	Prism, colourless
Z = 4	0.79 × 0.25 × 0.15 mm
F(000) = 592

Data collection

Bruker SMART CCD diffractometer	2344 independent reflections
Radiation source: fine-focus sealed tube	2176 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 8.192 pixels mm^-1	θmax = 26.3°, θmin = 2.1°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker 1999)	k = −12→12
Tmin = 0.26, Tmax = 0.62	l = −23→20
5977 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.023	H-atom parameters constrained
wR(F^2) = 0.054	w = 1/[σ^2(Fo^2) + (0.0193P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
2344 reflections	Δρmax = 0.26 e Å^−3
154 parameters	Δρmin = −0.55 e Å^−3
0 restraints	Absolute structure: Flack (1983), 951 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.070 (11)

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
Se	1.13690 (4)	0.77766 (3)	0.561673 (12)	0.02483 (8)
O1	0.6835 (3)	0.71750 (18)	0.71171 (8)	0.0245 (4)
O2	0.3667 (3)	0.78627 (18)	0.75023 (9)	0.0318 (4)
C3	0.8810 (4)	0.7828 (2)	0.69025 (11)	0.0207 (4)
H3	1.0067	0.7282	0.7023	0.025*
C9	1.1551 (4)	0.5841 (2)	0.57378 (10)	0.0214 (5)
C10	0.9860 (4)	0.4981 (3)	0.55985 (14)	0.0271 (5)
H10	0.8540	0.5341	0.5476	0.033*
C5	0.6411 (5)	0.9524 (2)	0.72067 (11)	0.0221 (5)
H5	0.5911	1.0201	0.7547	0.027*
C14	1.3511 (5)	0.5302 (3)	0.59252 (11)	0.0254 (5)
H14	1.4643	0.5879	0.6031	0.031*
C2	0.8727 (4)	0.8190 (2)	0.61148 (10)	0.0200 (5)
H2	0.7515	0.7739	0.5888	0.024*
C1	0.8413 (4)	0.9743 (2)	0.61244 (11)	0.0215 (5)
H1	0.8701	1.0202	0.5678	0.026*
C7	0.9859 (4)	1.0171 (3)	0.67302 (12)	0.0235 (5)
H7A	1.1345	0.9951	0.6648	0.028*
H7B	0.9710	1.1129	0.6851	0.028*
C8	0.5423 (4)	0.8154 (3)	0.73009 (12)	0.0235 (5)
C6	0.6205 (5)	1.0010 (2)	0.64311 (11)	0.0244 (5)
H6A	0.5124	0.9491	0.6184	0.029*
H6B	0.5848	1.0973	0.6408	0.029*
C4	0.8815 (5)	0.9229 (2)	0.72617 (11)	0.0220 (5)
H4	0.9416	0.9253	0.7736	0.026*
C11	1.0139 (5)	0.3586 (3)	0.56414 (16)	0.0338 (6)
H11	0.8997	0.3005	0.5554	0.041*
C13	1.3771 (5)	0.3902 (3)	0.59544 (13)	0.0314 (6)
H13	1.5092	0.3537	0.6071	0.038*
C12	1.2101 (5)	0.3049 (3)	0.58133 (13)	0.0323 (7)
H12	1.2288	0.2108	0.5833	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se	0.02975 (14)	0.02018 (12)	0.02455 (12)	−0.00081 (11)	0.00971 (11)	−0.00075 (10)
O1	0.0237 (10)	0.0210 (8)	0.0287 (8)	−0.0029 (8)	0.0046 (7)	0.0033 (7)
O2	0.0203 (9)	0.0348 (10)	0.0402 (9)	−0.0021 (10)	0.0052 (8)	0.0064 (8)
C3	0.0196 (11)	0.0207 (11)	0.0218 (10)	0.0007 (12)	0.0005 (9)	0.0040 (9)
C9	0.0258 (14)	0.0235 (12)	0.0151 (11)	0.0018 (10)	0.0056 (10)	−0.0004 (8)
C10	0.0233 (13)	0.0269 (13)	0.0311 (13)	0.0013 (10)	−0.0053 (12)	−0.0013 (12)
C5	0.0253 (14)	0.0197 (12)	0.0214 (11)	−0.0003 (12)	0.0049 (12)	−0.0014 (9)
C14	0.0227 (14)	0.0301 (13)	0.0235 (11)	−0.0010 (13)	0.0018 (11)	0.0002 (10)
C2	0.0212 (12)	0.0213 (11)	0.0173 (10)	0.0000 (11)	0.0027 (10)	−0.0013 (8)
C1	0.0262 (14)	0.0203 (12)	0.0181 (10)	−0.0011 (11)	0.0001 (10)	0.0021 (9)
C7	0.0233 (14)	0.0238 (13)	0.0234 (12)	−0.0038 (11)	0.0012 (10)	−0.0013 (10)
C8	0.0233 (14)	0.0270 (14)	0.0203 (11)	0.0012 (10)	−0.0013 (10)	0.0027 (10)
C6	0.0263 (13)	0.0205 (12)	0.0264 (11)	0.0023 (12)	−0.0037 (11)	0.0031 (9)
C4	0.0232 (13)	0.0271 (12)	0.0156 (10)	−0.0020 (12)	0.0002 (10)	−0.0002 (9)
C11	0.0348 (16)	0.0271 (14)	0.0395 (14)	−0.0058 (11)	−0.0031 (14)	−0.0021 (14)
C13	0.0265 (15)	0.0385 (15)	0.0292 (12)	0.0090 (13)	0.0050 (12)	0.0067 (11)
C12	0.0401 (16)	0.0237 (15)	0.0333 (14)	0.0041 (11)	0.0101 (11)	0.0044 (10)

Geometric parameters (Å, º)

Se—C9	1.913 (2)	C14—H14	0.9300
Se—C2	1.954 (3)	C2—C1	1.534 (3)
O1—C8	1.352 (3)	C2—H2	0.9800
O1—C3	1.453 (3)	C1—C7	1.528 (3)
O2—C8	1.202 (3)	C1—C6	1.527 (4)
C3—C4	1.534 (3)	C1—H1	0.9800
C3—C2	1.544 (3)	C7—C4	1.520 (3)
C3—H3	0.9800	C7—H7A	0.9700
C9—C10	1.380 (4)	C7—H7B	0.9700
C9—C14	1.385 (4)	C6—H6A	0.9700
C10—C11	1.380 (4)	C6—H6B	0.9700
C10—H10	0.9300	C4—H4	0.9800
C5—C8	1.489 (3)	C11—C12	1.379 (4)
C5—C4	1.540 (4)	C11—H11	0.9300
C5—C6	1.560 (3)	C13—C12	1.367 (4)
C5—H5	0.9800	C13—H13	0.9300
C14—C13	1.382 (4)	C12—H12	0.9300
C9—Se—C2	101.36 (10)	C6—C1—H1	114.9
C8—O1—C3	108.70 (18)	C2—C1—H1	114.9
O1—C3—C4	105.63 (19)	C4—C7—C1	94.7 (2)
O1—C3—C2	110.25 (19)	C4—C7—H7A	112.8
C4—C3—C2	103.26 (18)	C1—C7—H7A	112.8
O1—C3—H3	112.4	C4—C7—H7B	112.8
C4—C3—H3	112.4	C1—C7—H7B	112.8
C2—C3—H3	112.4	H7A—C7—H7B	110.3
C10—C9—C14	120.0 (2)	O2—C8—O1	121.1 (2)
C10—C9—Se	122.3 (2)	O2—C8—C5	129.4 (2)
C14—C9—Se	117.5 (2)	O1—C8—C5	109.5 (2)
C9—C10—C11	119.6 (2)	C1—C6—C5	103.6 (2)
C9—C10—H10	120.2	C1—C6—H6A	111.0
C11—C10—H10	120.2	C5—C6—H6A	111.0
C8—C5—C4	103.3 (2)	C1—C6—H6B	111.0
C8—C5—C6	110.8 (2)	C5—C6—H6B	111.0
C4—C5—C6	101.72 (19)	H6A—C6—H6B	109.0
C8—C5—H5	113.3	C7—C4—C3	104.26 (18)
C4—C5—H5	113.3	C7—C4—C5	105.3 (2)
C6—C5—H5	113.3	C3—C4—C5	97.78 (19)
C13—C14—C9	119.5 (3)	C7—C4—H4	115.8
C13—C14—H14	120.2	C3—C4—H4	115.8
C9—C14—H14	120.2	C5—C4—H4	115.8
C1—C2—C3	102.73 (17)	C12—C11—C10	120.3 (3)
C1—C2—Se	108.67 (16)	C12—C11—H11	119.8
C3—C2—Se	113.39 (17)	C10—C11—H11	119.8
C1—C2—H2	110.6	C12—C13—C14	120.5 (3)
C3—C2—H2	110.6	C12—C13—H13	119.8
Se—C2—H2	110.6	C14—C13—H13	119.8
C7—C1—C6	101.68 (18)	C13—C12—C11	119.9 (3)
C7—C1—C2	101.84 (19)	C13—C12—H12	120.0
C6—C1—C2	106.9 (2)	C11—C12—H12	120.0
C7—C1—H1	114.9
C8—O1—C3—C4	23.7 (2)	C4—C5—C8—O2	155.8 (3)
C8—O1—C3—C2	−87.2 (2)	C6—C5—C8—O2	−95.9 (3)
C2—Se—C9—C10	49.5 (2)	C4—C5—C8—O1	−24.4 (2)
C2—Se—C9—C14	−135.11 (17)	C6—C5—C8—O1	83.9 (2)
C14—C9—C10—C11	−0.5 (4)	C7—C1—C6—C5	−39.9 (2)
Se—C9—C10—C11	174.8 (2)	C2—C1—C6—C5	66.5 (2)
C10—C9—C14—C13	1.6 (3)	C8—C5—C6—C1	−101.8 (2)
Se—C9—C14—C13	−173.95 (17)	C4—C5—C6—C1	7.5 (2)
O1—C3—C2—C1	105.7 (2)	C1—C7—C4—C3	51.2 (2)
C4—C3—C2—C1	−6.8 (3)	C1—C7—C4—C5	−51.1 (2)
O1—C3—C2—Se	−137.26 (16)	O1—C3—C4—C7	−144.1 (2)
C4—C3—C2—Se	110.28 (19)	C2—C3—C4—C7	−28.3 (3)
C9—Se—C2—C1	175.36 (15)	O1—C3—C4—C5	−36.2 (2)
C9—Se—C2—C3	61.81 (18)	C2—C3—C4—C5	79.6 (2)
C3—C2—C1—C7	39.4 (2)	C8—C5—C4—C7	142.70 (19)
Se—C2—C1—C7	−80.99 (18)	C6—C5—C4—C7	27.7 (2)
C3—C2—C1—C6	−66.9 (2)	C8—C5—C4—C3	35.55 (19)
Se—C2—C1—C6	172.75 (14)	C6—C5—C4—C3	−79.40 (19)
C6—C1—C7—C4	55.0 (2)	C9—C10—C11—C12	−0.9 (4)
C2—C1—C7—C4	−55.3 (2)	C9—C14—C13—C12	−1.3 (4)
C3—O1—C8—O2	−179.6 (2)	C14—C13—C12—C11	−0.1 (4)
C3—O1—C8—C5	0.6 (2)	C10—C11—C12—C13	1.2 (4)