1-Adamantyl propargyl ether

1-Adamantyl propargyl ether, C₁₃H₁₈O, crystallizes in the `extended' conformation with a close contact between the acetyl­enic H atom and the O atom of an adjacent mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.092
• Data-to-parameter ratio = 14.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           30.00
         From the CIF: _reflns_number_total               1808
         Count of symmetry unique reflns         1807
         Completeness (_total/calc)            100.06%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         1
         Fraction of Friedel pairs measured     0.001
         Are heavy atom types Z>Si present           no
          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.

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S1. Comment

1-Adamantyl propargyl ether, (I), has been found to selectively inactivate the 2B5 form of rabbit cytochrome P-450 (Strobel et al., 1999). In order to provide data for computer-modelling studies of the docking of (I) with the enzyme, the structure of (I) (Fig. 1) was determined. The compound crystallizes in the `extended' conformation as the result of weak hydrogen bonding between the acetylenic H atom (H13 attached to C13) and the O atom of a neighboring molecule. This leads to the formation of spiral chains of molecules running parallel to a (Fig. 2 and Table 1).

S2. Experimental

Compound (I) was prepared as reported in the literature (Strobel et al., 1999) and recrystallized from a propan-2-ol/water mixture.

Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPAK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPAK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. Perspective view of (I). Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented by spheres of arbitrary radii.
	Fig. 2. View of the hydrogen-bonding interaction in (I).

1-(2-propynyloxy)-tricyclo[3.3.1.1^3,7]decane

Crystal data

C13H18O	Dx = 1.178 Mg m^−3
Mr = 190.27	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 10416 reflections
a = 7.4432 (2) Å	θ = 2.5–30.0°
b = 10.9094 (2) Å	µ = 0.07 mm^−1
c = 13.2137 (4) Å	T = 120 K
V = 1072.96 (5) Å^3	Block, colourless
Z = 4	0.23 × 0.18 × 0.17 mm
F(000) = 416

Data collection

Nonius KappaCCD (with Oxford Cryosystems Cryostream coller) diffractometer	1808 independent reflections
Radiation source: fine-focus sealed tube	1579 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω scans with κ offsets	θmax = 30.0°, θmin = 3.1°
Absorption correction: multi-scan (HKL SCALEPAK; Otwinowski & Minor, 1997)	h = −10→10
Tmin = 0.984, Tmax = 0.988	k = −15→15
10416 measured reflections	l = −18→18

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0367P)^2 + 0.2443P] where P = (Fo^2 + 2Fc^2)/3
1808 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.22 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
O	0.01556 (14)	0.82489 (9)	0.81781 (8)	0.0231 (2)
C1	−0.12312 (19)	0.86183 (12)	0.74667 (10)	0.0185 (3)
C2	−0.2046 (2)	0.74062 (13)	0.71162 (12)	0.0259 (3)
H2A	−0.2525	0.6954	0.7707	0.034*
H2B	−0.1104	0.6896	0.6797	0.034*
C3	−0.3564 (2)	0.76406 (14)	0.63543 (11)	0.0249 (3)
H3	−0.4090	0.6842	0.6131	0.032*
C4	−0.5015 (2)	0.84188 (16)	0.68574 (13)	0.0325 (4)
H4A	−0.5527	0.7972	0.7443	0.042*
H4B	−0.5997	0.8582	0.6370	0.042*
C5	−0.4197 (2)	0.96290 (16)	0.72125 (15)	0.0377 (4)
H5	−0.5152	1.0137	0.7541	0.049*
C6	−0.3435 (3)	1.03252 (16)	0.63068 (17)	0.0453 (5)
H6A	−0.2909	1.1111	0.6535	0.059*
H6B	−0.4408	1.0508	0.5819	0.059*
C7	−0.1986 (3)	0.95438 (18)	0.57933 (13)	0.0380 (4)
H7	−0.1493	0.9996	0.5197	0.049*
C8	−0.0466 (2)	0.92950 (16)	0.65548 (12)	0.0284 (4)
H8A	0.0482	0.8793	0.6232	0.037*
H8B	0.0077	1.0079	0.6775	0.037*
C9	−0.2794 (2)	0.83222 (17)	0.54396 (12)	0.0325 (4)
H9A	−0.3757	0.8477	0.4939	0.042*
H9B	−0.1855	0.7817	0.5112	0.042*
C10	−0.2688 (2)	0.93883 (16)	0.79773 (13)	0.0297 (4)
H10A	−0.2173	1.0176	0.8212	0.039*
H10B	−0.3171	0.8946	0.8572	0.039*
C11	0.1189 (2)	0.92254 (14)	0.85968 (12)	0.0249 (3)
H11A	0.0384	0.9838	0.8914	0.032*
H11B	0.1885	0.9638	0.8056	0.032*
C12	0.2411 (2)	0.87175 (14)	0.93563 (12)	0.0241 (3)
C13	0.3398 (2)	0.83105 (15)	0.99742 (12)	0.0291 (3)
H13	0.4190	0.7984	1.0470	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O	0.0262 (5)	0.0195 (5)	0.0237 (5)	−0.0017 (4)	−0.0068 (4)	0.0026 (4)
C1	0.0197 (6)	0.0188 (6)	0.0171 (6)	0.0007 (5)	−0.0009 (6)	0.0018 (5)
C2	0.0309 (8)	0.0188 (7)	0.0280 (7)	−0.0013 (6)	−0.0047 (7)	0.0003 (6)
C3	0.0259 (7)	0.0232 (7)	0.0255 (7)	−0.0027 (6)	−0.0033 (6)	−0.0025 (6)
C4	0.0209 (7)	0.0436 (9)	0.0329 (9)	−0.0010 (7)	−0.0007 (7)	−0.0073 (7)
C5	0.0277 (8)	0.0368 (9)	0.0487 (11)	0.0134 (7)	−0.0100 (8)	−0.0169 (8)
C6	0.0497 (11)	0.0247 (8)	0.0615 (13)	0.0021 (8)	−0.0315 (11)	0.0055 (8)
C7	0.0419 (10)	0.0456 (10)	0.0266 (8)	−0.0171 (8)	−0.0119 (8)	0.0162 (8)
C8	0.0262 (8)	0.0378 (8)	0.0211 (7)	−0.0092 (7)	−0.0018 (6)	0.0069 (6)
C9	0.0309 (8)	0.0466 (10)	0.0201 (7)	−0.0038 (8)	−0.0038 (7)	−0.0006 (7)
C10	0.0258 (7)	0.0350 (8)	0.0282 (8)	0.0039 (7)	−0.0023 (7)	−0.0122 (7)
C11	0.0265 (7)	0.0219 (7)	0.0264 (7)	−0.0009 (6)	−0.0047 (7)	0.0011 (6)
C12	0.0255 (7)	0.0234 (7)	0.0233 (7)	−0.0015 (6)	0.0000 (6)	−0.0008 (6)
C13	0.0303 (8)	0.0295 (8)	0.0276 (7)	−0.0007 (7)	−0.0047 (7)	0.0009 (7)

Geometric parameters (Å, º)

O—C11	1.4258 (18)	C4—C5	1.528 (2)
O—C1	1.4531 (16)	C5—C6	1.527 (3)
C1—C8	1.5235 (19)	C5—C10	1.534 (2)
C1—C2	1.5268 (19)	C6—C7	1.533 (3)
C1—C10	1.528 (2)	C7—C9	1.535 (3)
C2—C3	1.535 (2)	C7—C8	1.538 (2)
C3—C4	1.526 (2)	C11—C12	1.463 (2)
C3—C9	1.530 (2)	C12—C13	1.185 (2)
C11—O—C1	115.28 (10)	C6—C5—C4	109.71 (16)
O—C1—C8	112.37 (11)	C6—C5—C10	109.23 (15)
O—C1—C2	103.78 (11)	C4—C5—C10	110.26 (15)
C8—C1—C2	109.16 (12)	C5—C6—C7	109.38 (14)
O—C1—C10	111.76 (11)	C6—C7—C9	109.99 (15)
C8—C1—C10	110.36 (13)	C6—C7—C8	109.02 (15)
C2—C1—C10	109.15 (12)	C9—C7—C8	109.52 (15)
C1—C2—C3	110.31 (12)	C1—C8—C7	109.15 (12)
C4—C3—C9	109.80 (14)	C3—C9—C7	109.16 (13)
C4—C3—C2	109.14 (13)	C1—C10—C5	108.84 (12)
C9—C3—C2	108.86 (13)	O—C11—C12	108.58 (12)
C3—C4—C5	109.42 (13)	C13—C12—C11	179.69 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O^i	0.95	2.35	3.251 (2)	158

Symmetry code: (i) x+1/2, −y+3/2, −z+2.