syn,syn-15,17-Di-2-naphthyl­hexa­cyclo­[10.2.1.13,10.15,8.02,11.04,9]hepta­decane deuterochloro­form monosolvate

DeBlase, A.F.; Thong, D.C.; Nadeau, J.M.; Gebhart, D.; Provo, J.; Foxman, B.M.

doi:10.1107/S160053680903565X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages o2427-o2428

doi:10.1107/S160053680903565X

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syn,syn-15,17-Di-2-naphthylhexacyclo[10.2.1.1^3,10.1^5,8.0^2,11.0^4,9]heptadecane deuterochloroform monosolvate

Andrew F. DeBlase,^a Darence Ca Thong,^a Jocelyn M. Nadeau,^a ^* David Gebhart,^b Jonathan Provo ^b and Bruce M. Foxman ^c

^aDepartment of Chemistry, Biochemistry and Physics, Marist College, Poughkeepsie, NY 12601, USA, ^bOlin College, Needham, MA 02492, USA, and ^cDepartment of Chemistry, MS015, Brandeis University, Waltham, MA 02454, USA
^*Correspondence e-mail: jocelyn.nadeau@marist.edu

(Received 20 August 2009; accepted 3 September 2009; online 12 September 2009)

The main molecule of the title compound, C₃₇H₃₆·CDCl₃, is a hydrocarbon with two naphthalene segments attached to opposite ends of a rigid norbornylogous spacer with an overall structure that is approximately C-shaped. The dihedral angle between the naphthalene ring planes is 9.27 (7)°. The cleft that exists between the naphthalene rings is large enough that the compound crystallizes with a solvent molecule (CDCl₃) in the cleft. The CDCl₃ solvent molecule is present in two disordered orientations in a 3:2 ratio, each involving C—D⋯π to C₆ ring centers.

Related literature

For examples of related molecules with C-shaped topologies, see: Chou et al. (2005 ); Klärner et al. (2001 ); Kurebayashi et al. (2001 ); Nemoto et al. (2000 ). For examples of related molecules with the same norbornyl skeleton, see: Bodige et al. (1999 ); Nadeau et al. (2003 ). For the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₃₈H₃₇Cl₃
M_r = 600.07
Triclinic, $[P \overline 1]$
a = 6.0833 (4) Å
b = 14.6343 (10) Å
c = 16.2725 (12) Å
α = 93.641 (5)°
β = 94.437 (4)°
γ = 90.770 (4)°
V = 1441.15 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 120 K
0.59 × 0.29 × 0.24 mm

Data collection

Area diffractometer
Absorption correction: multi-scan (APEX2; Bruker, 2006 ) T_min = 0.90, T_max = 0.92
18141 measured reflections
5889 independent reflections
4451 reflections with I > 2.0σ(I)
R_int = 0.074

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.162
S = 1.00
5889 reflections
505 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.83 e Å⁻³

Table 1
C—D⋯π interactions (Å, °)

C—D⋯Cg	C—D	D⋯Cg	D⋯Cg	C—D⋯Cg
C38—H381⋯Cg1	0.97	2.44	3.399	173
C381—H3811⋯Cg2	0.98	2.61	3.521	154
Cg1 is the centroid of the C30–C37 ring andCg2 is the centroid of the C4–C10 ring.

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: APEX2 (Bruker, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: CAMERON (Watkin et al., 1996 ); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903565X/jj2006sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680903565X/jj2006Isup2.hkl

checkCIF report

Comment top

The structure of the title compound, C₃₇H₃₆^.CDCl₃, consists of two naphthalene rings connected to opposite ends of a rigid, norbornylogous hydrocarbon spacer. The overall topology of the molecule is roughly C-shaped, and the cleft that exists between the rings allows for inclusion of a molecule of crystallization, chloroform-d (CDCl₃), as shown in Figs. 1 and 2. Although the naphthalene rings can rotate freely about the C—C bond through which they are attached to the rigid spacer, they are only found in a cofacially stacked, eclipsed conformation. The anti conformer is not observed. The CDCl₃ within the cleft is in two disordered orientations, occurring in about a 3:2 ratio. Both orientations show interactions with different areas of the naphthalene rings. The most common orientation shows coordination between the chloroform deuterium atom and the π system of the distal ring of the naphthyl group. In this orientation, the C···π and D···π distances are 3.399 and 2.44 Å, repectively, with a C—D···π angle of 172.7°. In the other orientation, the C···π and D···π distances are 3.521 and 2.61 Å, repectively, with a C—D···π angle of 153.9°. To establish the context for the measurements associated with this interaction, the Cambridge Structural Database (Allen, 2002: Version 5.30, including May 2009 updates) was searched for homologous structure-solvent motifs. The search results are organized into two histograms, one for the H(D)···π distance (Fig. 3) and one for the C—H(D)···π angle (Fig. 4). The histograms support the observations, with the values for distance and angle falling well within the range of previously observed values. The observed C···π distance of 3.399 Å was on the low end of recorded distances, whereas the angle of 172.7° was binned at the higher end of the angle range.

Related literature top

For examples of related molecules with C-shaped topologies, see: Chou et al. (2005); Klärner et al. (2001); Kurebayashi et al. (2001); Nemoto et al. (2000). For examples of related molecules with the same norbornyl skeleton, see: Bodige et al. (1999); Nadeau et al. (2003). For the Cambridge Structural Database, see: Allen (2002). Cg1 is the centroid of the C30—C37 ring and

Cg2 is the centroid of the C4–C10 ring.

Experimental top

Triethylsilane (94 µL; 0.588 mmol) and trifluoroacetic acid (44 µL; 0.588 mmol) were added to a stirring suspension of 15,17-di-2-naphthylhexacyclo[10.2.1.1^3,10.1^5,8.0^2,11.0^4,9]heptadecane-15,17-diol (25 mg; 0.049 mmol) in CH₂Cl₂ under nitrogen. Upon adding the trifluoroacetic acid, the solid gradually went into solution, and the reaction was refluxed for two hours. Upon cooling, solid sodium bicarbonate was added. After 30 minutes, the reaction mixture was filtered and concentrated under reduced pressure. The crude solid was purified by preparative TLC on silica gel (30% CH₂Cl₂ in petroleum ether) to give the title compound as the major diastereomer (with evidence of at least one additional diastereomer by NMR) as an off-white solid in 42% yield (10 mg). Single crystals suitable for crystallographic analysis were obtained by slow vapor diffusion of hexanes into a solution of the compound dissolved in chloroform-d at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: APEX2 (Bruker, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top

	Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. The major component [0.60 (1)] of the disordered CDCl₃ solvate is shown.
	Fig. 2. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. The minor component [0.40 (1)] of the disordered CDCl₃ solvate is shown.
	Fig. 3. Histogram of C···π distance versus number of structures (378 REFCODES, 443 data points).
	Fig. 4. Histogram of C—H···π angle versus number of structures (378 REFCODES, 443 data points).

syn,syn-15,17-Di-2-naphthylhexacyclo[10.2.1.1^3,10.1^5,8.0^2,11.0^4,9]heptadecane deuterochloroform monosolvate top

Crystal data top

C₃₈H₃₇Cl₃	Z = 2
M_r = 600.07	F(000) = 632
Triclinic, P1	D_x = 1.383 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0833 (4) Å	Cell parameters from 4571 reflections
b = 14.6343 (10) Å	θ = 3–26°
c = 16.2725 (12) Å	µ = 0.35 mm⁻¹
α = 93.641 (5)°	T = 120 K
β = 94.437 (4)°	Acicular, colourless
γ = 90.770 (4)°	0.59 × 0.29 × 0.24 mm
V = 1441.15 (17) Å³

Data collection top

Area diffractometer	5889 independent reflections
Radiation source: fine-focus sealed tube	4451 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.074
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.4°
Absorption correction: multi-scan (APEX2; Bruker, 2006)	h = −7→7
T_min = 0.90, T_max = 0.92	k = −18→18
18141 measured reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Method = Modified Sheldrick w = 1/[σ²(F²) + (0.09P)² + 0.62P], where P = (max(F_o²,0) + 2F_c²)/3
5889 reflections	(Δ/σ)_max = 0.005
505 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.83 e Å⁻³
0 constraints

Crystal data top

C₃₈H₃₇Cl₃	γ = 90.770 (4)°
M_r = 600.07	V = 1441.15 (17) Å³
Triclinic, P1	Z = 2
a = 6.0833 (4) Å	Mo Kα radiation
b = 14.6343 (10) Å	µ = 0.35 mm⁻¹
c = 16.2725 (12) Å	T = 120 K
α = 93.641 (5)°	0.59 × 0.29 × 0.24 mm
β = 94.437 (4)°

Data collection top

Area diffractometer	5889 independent reflections
Absorption correction: multi-scan (APEX2; Bruker, 2006)	4451 reflections with I > 2.0σ(I)
T_min = 0.90, T_max = 0.92	R_int = 0.074
18141 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.56 e Å⁻³
5889 reflections	Δρ_min = −0.83 e Å⁻³
505 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.9320 (6)	0.2872 (2)	0.1765 (2)	0.0336	0.600 (10)
Cl2	1.0165 (7)	0.4616 (3)	0.1051 (3)	0.0301	0.600 (10)
Cl3	0.6094 (4)	0.4332 (3)	0.18090 (16)	0.0440	0.600 (10)
Cl4	0.9649 (15)	0.2877 (5)	0.1738 (5)	0.0836	0.400 (10)
Cl5	0.9765 (16)	0.4486 (6)	0.0912 (6)	0.0735	0.400 (10)
Cl6	0.5802 (11)	0.4017 (5)	0.1684 (4)	0.0928	0.400 (10)
C1	0.7151 (4)	0.66524 (17)	0.32622 (16)	0.0234
C2	0.9142 (4)	0.67093 (17)	0.28739 (15)	0.0239
C3	1.0658 (4)	0.60376 (16)	0.29452 (15)	0.0219
C4	1.0253 (4)	0.52624 (16)	0.33995 (14)	0.0184
C5	0.8249 (4)	0.52025 (15)	0.37930 (14)	0.0179
C6	0.6729 (4)	0.59234 (16)	0.37159 (15)	0.0202
C7	1.1743 (4)	0.45312 (16)	0.34613 (15)	0.0201
C8	1.1285 (4)	0.37861 (16)	0.38892 (14)	0.0190
C9	0.9303 (4)	0.37194 (15)	0.42908 (13)	0.0162
C10	0.7845 (4)	0.44253 (16)	0.42341 (14)	0.0175
C11	0.8895 (3)	0.29369 (15)	0.48275 (14)	0.0159
C12	1.0068 (4)	0.20154 (15)	0.46699 (14)	0.0159
C13	0.9271 (4)	0.14916 (16)	0.53826 (14)	0.0194
C14	0.6849 (4)	0.18168 (16)	0.54398 (14)	0.0199
C15	0.6560 (4)	0.24780 (15)	0.47487 (14)	0.0167
C16	0.6501 (3)	0.20180 (14)	0.38662 (13)	0.0137
C17	0.8948 (3)	0.16819 (14)	0.38136 (14)	0.0143
C18	0.8645 (3)	0.06545 (15)	0.35275 (13)	0.0150
C19	0.6558 (4)	0.03744 (15)	0.39369 (14)	0.0166
C20	0.5112 (4)	0.11355 (15)	0.35897 (13)	0.0156
C21	0.5351 (3)	0.10019 (15)	0.26463 (14)	0.0152
C22	0.7780 (3)	0.06515 (14)	0.26049 (13)	0.0144
C23	0.3984 (3)	0.02792 (15)	0.20792 (14)	0.0158
C24	0.7472 (4)	−0.02281 (15)	0.20291 (14)	0.0161
C25	0.6271 (4)	−0.10214 (16)	0.23961 (15)	0.0181
C26	0.3867 (4)	−0.06678 (16)	0.24400 (16)	0.0194
C27	0.5594 (4)	0.00657 (15)	0.14019 (14)	0.0158
C28	0.6114 (4)	0.08106 (15)	0.08410 (14)	0.0163
C29	0.4645 (4)	0.14835 (16)	0.06462 (14)	0.0191
C30	0.5074 (4)	0.21408 (15)	0.00734 (14)	0.0178
C31	0.7088 (4)	0.21017 (16)	−0.03175 (14)	0.0187
C32	0.8588 (4)	0.14046 (16)	−0.01134 (15)	0.0196
C33	0.8119 (4)	0.07889 (16)	0.04453 (14)	0.0190
C34	0.3567 (4)	0.28382 (17)	−0.01205 (16)	0.0243
C35	0.4032 (4)	0.34658 (19)	−0.06702 (17)	0.0305
C36	0.6024 (4)	0.34290 (18)	−0.10577 (16)	0.0293
C37	0.7516 (4)	0.27660 (17)	−0.08869 (15)	0.0239
C38	0.8210 (7)	0.3799 (3)	0.1248 (3)	0.0265 (13)*	0.600 (10)
C381	0.8524 (14)	0.3936 (6)	0.1721 (7)	0.048 (3)*	0.400 (10)
H11	0.607 (5)	0.7098 (19)	0.3195 (17)	0.0275*
H21	0.943 (4)	0.725 (2)	0.2548 (17)	0.0293*
H31	1.208 (5)	0.6084 (18)	0.2710 (17)	0.0260*
H61	0.530 (4)	0.5875 (18)	0.4020 (16)	0.0252*
H71	1.315 (4)	0.4588 (18)	0.3205 (16)	0.0237*
H81	1.223 (4)	0.3286 (19)	0.3925 (16)	0.0234*
H101	0.647 (4)	0.4421 (17)	0.4477 (16)	0.0208*
H111	0.932 (4)	0.3167 (17)	0.5370 (16)	0.0189*
H121	1.169 (4)	0.2040 (17)	0.4708 (15)	0.0190*
H131	1.020 (4)	0.1663 (18)	0.5902 (17)	0.0233*
H132	0.930 (4)	0.0838 (19)	0.5293 (16)	0.0218*
H141	0.675 (4)	0.2147 (18)	0.5985 (17)	0.0245*
H142	0.572 (4)	0.1300 (19)	0.5386 (16)	0.0239*
H151	0.534 (4)	0.2870 (18)	0.4797 (15)	0.0192*
H161	0.616 (4)	0.2521 (17)	0.3478 (15)	0.0158*
H171	0.966 (4)	0.2026 (17)	0.3373 (15)	0.0165*
H181	1.006 (4)	0.0277 (17)	0.3629 (15)	0.0184*
H191	0.676 (4)	0.0403 (17)	0.4514 (17)	0.0189*
H192	0.601 (4)	−0.0250 (18)	0.3766 (15)	0.0196*
H201	0.356 (4)	0.1180 (17)	0.3726 (15)	0.0185*
H211	0.511 (4)	0.1604 (17)	0.2381 (15)	0.0177*
H221	0.867 (4)	0.1082 (17)	0.2315 (15)	0.0158*
H231	0.249 (4)	0.0489 (17)	0.1887 (15)	0.0189*
H241	0.888 (4)	−0.0443 (17)	0.1796 (15)	0.0187*
H251	0.703 (4)	−0.1205 (17)	0.2963 (16)	0.0207*
H252	0.632 (4)	−0.1557 (19)	0.2046 (16)	0.0218*
H261	0.343 (4)	−0.0617 (18)	0.2997 (17)	0.0229*
H262	0.279 (4)	−0.1069 (18)	0.2084 (16)	0.0223*
H271	0.506 (4)	−0.0479 (17)	0.1044 (15)	0.0188*
H291	0.319 (4)	0.1522 (18)	0.0904 (16)	0.0227*
H321	0.997 (4)	0.1389 (18)	−0.0381 (16)	0.0234*
H331	0.915 (4)	0.0338 (18)	0.0586 (16)	0.0222*
H341	0.228 (5)	0.2868 (19)	0.0184 (17)	0.0297*
H351	0.308 (5)	0.396 (2)	−0.0806 (18)	0.0354*
H361	0.633 (5)	0.389 (2)	−0.1449 (18)	0.0351*
H371	0.891 (5)	0.2712 (19)	−0.1160 (17)	0.0288*
H381	0.7479	0.3564	0.0729	0.0315*	0.600 (10)
H3811	0.9096	0.4268	0.2240	0.0571*	0.400 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0500 (11)	0.0233 (12)	0.0269 (13)	0.0005 (7)	−0.0086 (8)	0.0115 (9)
Cl2	0.0318 (9)	0.0239 (10)	0.0356 (10)	−0.0007 (7)	0.0087 (7)	0.0022 (7)
Cl3	0.0431 (9)	0.0483 (15)	0.0436 (11)	0.0073 (9)	0.0233 (7)	0.0010 (9)
Cl4	0.155 (6)	0.045 (3)	0.055 (3)	−0.006 (3)	0.039 (3)	0.000 (2)
Cl5	0.102 (5)	0.045 (3)	0.085 (5)	0.035 (3)	0.054 (3)	0.031 (3)
Cl6	0.091 (3)	0.061 (3)	0.130 (4)	−0.003 (2)	0.066 (3)	−0.038 (3)
C1	0.0247 (12)	0.0180 (12)	0.0273 (14)	0.0033 (10)	0.0002 (10)	0.0005 (10)
C2	0.0339 (14)	0.0195 (12)	0.0184 (12)	−0.0035 (10)	0.0031 (10)	0.0007 (10)
C3	0.0247 (12)	0.0218 (12)	0.0194 (12)	−0.0041 (10)	0.0070 (10)	−0.0014 (10)
C4	0.0203 (11)	0.0197 (11)	0.0145 (11)	−0.0040 (9)	0.0014 (8)	−0.0041 (9)
C5	0.0187 (11)	0.0159 (11)	0.0183 (12)	−0.0014 (9)	0.0012 (9)	−0.0037 (9)
C6	0.0190 (11)	0.0181 (11)	0.0230 (12)	−0.0007 (9)	0.0015 (9)	−0.0015 (9)
C7	0.0175 (11)	0.0215 (12)	0.0213 (12)	−0.0020 (9)	0.0046 (9)	−0.0025 (9)
C8	0.0158 (11)	0.0195 (12)	0.0211 (12)	0.0011 (9)	0.0015 (9)	−0.0035 (9)
C9	0.0166 (10)	0.0163 (11)	0.0146 (11)	−0.0022 (8)	−0.0010 (8)	−0.0039 (9)
C10	0.0144 (11)	0.0204 (12)	0.0176 (11)	−0.0028 (9)	0.0039 (9)	−0.0024 (9)
C11	0.0156 (11)	0.0162 (11)	0.0156 (11)	−0.0005 (8)	0.0012 (8)	−0.0018 (9)
C12	0.0134 (11)	0.0156 (11)	0.0185 (12)	−0.0007 (8)	0.0011 (8)	−0.0005 (9)
C13	0.0236 (12)	0.0172 (12)	0.0170 (12)	−0.0005 (9)	−0.0011 (9)	0.0003 (9)
C14	0.0252 (12)	0.0189 (12)	0.0160 (12)	0.0002 (10)	0.0047 (9)	0.0001 (9)
C15	0.0163 (11)	0.0154 (11)	0.0187 (12)	0.0002 (9)	0.0034 (8)	−0.0005 (9)
C16	0.0136 (10)	0.0134 (10)	0.0145 (11)	0.0011 (8)	0.0024 (8)	0.0019 (8)
C17	0.0124 (10)	0.0137 (10)	0.0170 (11)	0.0004 (8)	0.0035 (8)	−0.0001 (8)
C18	0.0134 (10)	0.0148 (11)	0.0170 (11)	−0.0005 (8)	0.0012 (8)	0.0020 (9)
C19	0.0190 (11)	0.0157 (11)	0.0148 (11)	−0.0019 (9)	0.0011 (9)	−0.0001 (9)
C20	0.0134 (10)	0.0170 (11)	0.0165 (11)	−0.0009 (8)	0.0041 (8)	−0.0014 (9)
C21	0.0125 (10)	0.0137 (11)	0.0196 (12)	0.0005 (8)	0.0029 (8)	0.0007 (9)
C22	0.0124 (10)	0.0131 (10)	0.0180 (11)	0.0008 (8)	0.0029 (8)	0.0008 (9)
C23	0.0112 (10)	0.0189 (11)	0.0173 (11)	0.0003 (8)	0.0010 (8)	0.0008 (9)
C24	0.0161 (11)	0.0156 (11)	0.0167 (11)	0.0017 (8)	0.0018 (8)	0.0004 (9)
C25	0.0192 (11)	0.0133 (11)	0.0219 (12)	0.0000 (9)	0.0029 (9)	−0.0013 (9)
C26	0.0169 (11)	0.0179 (11)	0.0229 (12)	−0.0040 (9)	0.0017 (9)	−0.0017 (9)
C27	0.0146 (10)	0.0152 (11)	0.0171 (11)	0.0004 (8)	0.0010 (8)	−0.0019 (9)
C28	0.0163 (11)	0.0163 (11)	0.0157 (11)	−0.0026 (8)	0.0007 (8)	−0.0040 (9)
C29	0.0165 (11)	0.0197 (12)	0.0208 (12)	−0.0002 (9)	0.0030 (9)	−0.0019 (9)
C30	0.0179 (11)	0.0167 (11)	0.0181 (11)	−0.0007 (9)	0.0005 (9)	−0.0026 (9)
C31	0.0201 (11)	0.0188 (11)	0.0164 (11)	−0.0033 (9)	0.0012 (9)	−0.0048 (9)
C32	0.0164 (11)	0.0212 (12)	0.0211 (12)	−0.0008 (9)	0.0054 (9)	−0.0042 (9)
C33	0.0163 (11)	0.0200 (12)	0.0202 (12)	0.0035 (9)	0.0012 (9)	−0.0038 (9)
C34	0.0221 (12)	0.0240 (13)	0.0274 (14)	0.0030 (10)	0.0026 (10)	0.0034 (10)
C35	0.0303 (14)	0.0263 (14)	0.0359 (16)	0.0060 (11)	0.0028 (11)	0.0094 (12)
C36	0.0386 (15)	0.0241 (13)	0.0262 (14)	−0.0012 (11)	0.0055 (11)	0.0071 (11)
C37	0.0252 (13)	0.0260 (13)	0.0207 (12)	−0.0037 (10)	0.0056 (10)	−0.0019 (10)

Geometric parameters (Å, º) top

Cl1—C38	1.756 (5)	C18—C22	1.552 (3)
Cl2—C38	1.736 (6)	C18—H181	1.04 (3)
Cl3—C38	1.794 (6)	C19—C20	1.537 (3)
Cl4—C381	1.704 (12)	C19—H191	0.94 (3)
Cl5—C381	1.795 (12)	C19—H192	0.98 (3)
Cl6—C381	1.658 (11)	C20—C21	1.553 (3)
C1—C2	1.413 (3)	C20—H201	0.99 (2)
C1—C6	1.368 (3)	C21—C22	1.575 (3)
C1—H11	0.94 (3)	C21—C23	1.548 (3)
C2—C3	1.361 (4)	C21—H211	1.01 (3)
C2—H21	1.00 (3)	C22—C24	1.544 (3)
C3—C4	1.422 (3)	C22—H221	0.99 (2)
C3—H31	0.98 (3)	C23—C26	1.542 (3)
C4—C5	1.425 (3)	C23—C27	1.550 (3)
C4—C7	1.415 (3)	C23—H231	0.99 (3)
C5—C6	1.417 (3)	C24—C25	1.540 (3)
C5—C10	1.412 (3)	C24—C27	1.556 (3)
C6—H61	1.04 (3)	C24—H241	1.01 (3)
C7—C8	1.367 (3)	C25—C26	1.563 (3)
C7—H71	0.98 (3)	C25—H251	1.05 (3)
C8—C9	1.421 (3)	C25—H252	0.94 (3)
C8—H81	0.94 (3)	C26—H261	0.96 (3)
C9—C10	1.373 (3)	C26—H262	1.00 (3)
C9—C11	1.513 (3)	C27—C28	1.511 (3)
C10—H101	0.95 (3)	C27—H271	0.99 (3)
C11—C12	1.550 (3)	C28—C29	1.374 (3)
C11—C15	1.556 (3)	C28—C33	1.423 (3)
C11—H111	0.94 (3)	C29—C30	1.417 (3)
C12—C13	1.535 (3)	C29—H291	1.01 (3)
C12—C17	1.550 (3)	C30—C31	1.424 (3)
C12—H121	0.99 (3)	C30—C34	1.415 (3)
C13—C14	1.562 (3)	C31—C32	1.416 (3)
C13—H131	1.00 (3)	C31—C37	1.420 (3)
C13—H132	0.96 (3)	C32—C33	1.363 (3)
C14—C15	1.531 (3)	C32—H321	0.98 (3)
C14—H141	0.99 (3)	C33—H331	0.94 (3)
C14—H142	1.01 (3)	C34—C35	1.364 (4)
C15—C16	1.545 (3)	C34—H341	0.96 (3)
C15—H151	0.95 (3)	C35—C36	1.408 (4)
C16—C17	1.580 (3)	C35—H351	0.95 (3)
C16—C20	1.556 (3)	C36—C37	1.365 (4)
C16—H161	1.01 (2)	C36—H361	0.98 (3)
C17—C18	1.550 (3)	C37—H371	0.99 (3)
C17—H171	1.02 (2)	C38—H381	0.965
C18—C19	1.541 (3)	C381—H3811	0.984

C2—C1—C6	120.4 (2)	C19—C20—H201	119.6 (14)
C2—C1—H11	120.8 (17)	C16—C20—H201	113.0 (14)
C6—C1—H11	118.8 (17)	C21—C20—H201	113.0 (14)
C1—C2—C3	120.3 (2)	C20—C21—C22	102.95 (17)
C1—C2—H21	119.3 (16)	C20—C21—C23	122.72 (18)
C3—C2—H21	120.4 (16)	C22—C21—C23	102.85 (17)
C2—C3—C4	120.7 (2)	C20—C21—H211	109.9 (14)
C2—C3—H31	121.5 (16)	C22—C21—H211	112.7 (14)
C4—C3—H31	117.7 (16)	C23—C21—H211	105.6 (14)
C3—C4—C5	119.1 (2)	C18—C22—C21	103.20 (17)
C3—C4—C7	122.6 (2)	C18—C22—C24	123.41 (18)
C5—C4—C7	118.3 (2)	C21—C22—C24	102.85 (16)
C4—C5—C6	118.4 (2)	C18—C22—H221	110.2 (14)
C4—C5—C10	118.8 (2)	C21—C22—H221	110.3 (14)
C6—C5—C10	122.7 (2)	C24—C22—H221	106.3 (14)
C5—C6—C1	121.0 (2)	C21—C23—C26	113.65 (18)
C5—C6—H61	117.2 (15)	C21—C23—C27	100.81 (16)
C1—C6—H61	121.8 (15)	C26—C23—C27	99.68 (18)
C4—C7—C8	121.2 (2)	C21—C23—H231	113.8 (14)
C4—C7—H71	117.8 (15)	C26—C23—H231	111.4 (14)
C8—C7—H71	121.0 (15)	C27—C23—H231	116.4 (15)
C7—C8—C9	121.3 (2)	C22—C24—C25	114.65 (19)
C7—C8—H81	122.5 (16)	C22—C24—C27	100.62 (17)
C9—C8—H81	116.2 (16)	C25—C24—C27	99.23 (17)
C8—C9—C10	118.0 (2)	C22—C24—H241	113.5 (14)
C8—C9—C11	121.1 (2)	C25—C24—H241	110.9 (14)
C10—C9—C11	120.7 (2)	C27—C24—H241	116.9 (14)
C5—C10—C9	122.4 (2)	C24—C25—C26	103.21 (18)
C5—C10—H101	114.9 (16)	C24—C25—H251	113.2 (14)
C9—C10—H101	122.6 (16)	C26—C25—H251	114.7 (14)
C9—C11—C12	119.44 (18)	C24—C25—H252	110.0 (16)
C9—C11—C15	118.04 (18)	C26—C25—H252	111.8 (16)
C12—C11—C15	93.27 (16)	H251—C25—H252	104 (2)
C9—C11—H111	105.1 (15)	C23—C26—C25	103.04 (17)
C12—C11—H111	108.2 (16)	C23—C26—H261	111.2 (16)
C15—C11—H111	112.6 (15)	C25—C26—H261	112.2 (15)
C11—C12—C13	99.73 (18)	C23—C26—H262	109.1 (15)
C11—C12—C17	100.98 (17)	C25—C26—H262	111.3 (15)
C13—C12—C17	113.39 (17)	H261—C26—H262	110 (2)
C11—C12—H121	116.4 (15)	C23—C27—C24	93.55 (17)
C13—C12—H121	109.7 (14)	C23—C27—C28	118.46 (19)
C17—C12—H121	115.4 (14)	C24—C27—C28	117.74 (18)
C12—C13—C14	103.27 (18)	C23—C27—H271	110.1 (14)
C12—C13—H131	110.0 (15)	C24—C27—H271	109.0 (14)
C14—C13—H131	111.4 (15)	C28—C27—H271	107.3 (14)
C12—C13—H132	114.3 (15)	C27—C28—C29	122.4 (2)
C14—C13—H132	110.5 (15)	C27—C28—C33	119.7 (2)
H131—C13—H132	107 (2)	C29—C28—C33	117.7 (2)
C13—C14—C15	102.96 (18)	C28—C29—C30	122.2 (2)
C13—C14—H141	108.2 (15)	C28—C29—H291	120.7 (15)
C15—C14—H141	110.5 (15)	C30—C29—H291	117.1 (15)
C13—C14—H142	113.8 (15)	C29—C30—C31	119.0 (2)
C15—C14—H142	113.4 (15)	C29—C30—C34	122.1 (2)
H141—C14—H142	108 (2)	C31—C30—C34	118.9 (2)
C14—C15—C11	99.77 (18)	C30—C31—C32	118.3 (2)
C14—C15—C16	114.65 (18)	C30—C31—C37	118.8 (2)
C11—C15—C16	100.76 (17)	C32—C31—C37	122.9 (2)
C14—C15—H151	113.5 (15)	C31—C32—C33	120.9 (2)
C11—C15—H151	117.2 (15)	C31—C32—H321	117.5 (15)
C16—C15—H151	110.2 (15)	C33—C32—H321	121.6 (15)
C15—C16—C17	102.56 (16)	C28—C33—C32	121.9 (2)
C15—C16—C20	122.89 (18)	C28—C33—H331	118.2 (16)
C17—C16—C20	102.65 (17)	C32—C33—H331	119.9 (16)
C15—C16—H161	106.0 (14)	C30—C34—C35	120.8 (2)
C17—C16—H161	111.2 (13)	C30—C34—H341	116.3 (17)
C20—C16—H161	111.0 (13)	C35—C34—H341	122.7 (17)
C12—C17—C16	102.74 (17)	C34—C35—C36	120.5 (2)
C12—C17—C18	122.80 (18)	C34—C35—H351	123.4 (18)
C16—C17—C18	103.31 (16)	C36—C35—H351	116.1 (18)
C12—C17—H171	108.3 (13)	C35—C36—C37	120.4 (2)
C16—C17—H171	108.7 (13)	C35—C36—H361	118.9 (17)
C18—C17—H171	110.0 (14)	C37—C36—H361	120.6 (17)
C17—C18—C19	102.78 (17)	C31—C37—C36	120.6 (2)
C17—C18—C22	104.64 (17)	C31—C37—H371	117.0 (16)
C19—C18—C22	101.88 (17)	C36—C37—H371	122.3 (16)
C17—C18—H181	113.6 (14)	Cl3—C38—Cl1	110.8 (3)
C19—C18—H181	118.4 (14)	Cl3—C38—Cl2	109.7 (3)
C22—C18—H181	113.8 (14)	Cl1—C38—Cl2	113.8 (3)
C18—C19—C20	95.48 (17)	Cl3—C38—H381	105.4
C18—C19—H191	112.9 (15)	Cl1—C38—H381	108.3
C20—C19—H191	114.2 (15)	Cl2—C38—H381	108.5
C18—C19—H192	114.0 (14)	Cl5—C381—Cl4	105.6 (7)
C20—C19—H192	114.2 (14)	Cl5—C381—Cl6	114.0 (7)
H191—C19—H192	106 (2)	Cl4—C381—Cl6	118.6 (6)
C19—C20—C16	102.68 (17)	Cl5—C381—H3811	105.9
C19—C20—C21	102.59 (17)	Cl4—C381—H3811	105.6
C16—C20—C21	104.22 (17)	Cl6—C381—H3811	106.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C38—H381···Cg1	0.97	2.44	3.399	173
C381—H3811···Cg2	0.98	2.61	3.521	154

Experimental details

Crystal data
Chemical formula	C₃₈H₃₇Cl₃
M_r	600.07
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	6.0833 (4), 14.6343 (10), 16.2725 (12)
α, β, γ (°)	93.641 (5), 94.437 (4), 90.770 (4)
V (Å³)	1441.15 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.59 × 0.29 × 0.24

Data collection
Diffractometer	Area diffractometer
Absorption correction	Multi-scan (APEX2; Bruker, 2006)
T_min, T_max	0.90, 0.92
No. of measured, independent and observed [I > 2.0σ(I)] reflections	18141, 5889, 4451
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.162, 1.00
No. of reflections	5889
No. of parameters	505
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.83

Computer programs: APEX2 (Bruker, 2006), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996).

Selected geometric parameters (Å, º) top

Cl1—C38	1.756 (5)	C16—C20	1.556 (3)
Cl2—C38	1.736 (6)	C17—C18	1.550 (3)
Cl3—C38	1.794 (6)	C18—C19	1.541 (3)
Cl4—C381	1.704 (12)	C18—C22	1.552 (3)
Cl5—C381	1.795 (12)	C19—C20	1.537 (3)
Cl6—C381	1.658 (11)	C20—C21	1.553 (3)
C1—C2	1.413 (3)	C21—C22	1.575 (3)
C1—C6	1.368 (3)	C21—C23	1.548 (3)
C2—C3	1.361 (4)	C22—C24	1.544 (3)
C3—C4	1.422 (3)	C23—C26	1.542 (3)
C4—C5	1.425 (3)	C23—C27	1.550 (3)
C4—C7	1.415 (3)	C24—C25	1.540 (3)
C5—C6	1.417 (3)	C24—C27	1.556 (3)
C5—C10	1.412 (3)	C25—C26	1.563 (3)
C7—C8	1.367 (3)	C27—C28	1.511 (3)
C8—C9	1.421 (3)	C28—C29	1.374 (3)
C9—C10	1.373 (3)	C28—C33	1.423 (3)
C9—C11	1.513 (3)	C29—C30	1.417 (3)
C11—C12	1.550 (3)	C30—C31	1.424 (3)
C11—C15	1.556 (3)	C30—C34	1.415 (3)
C12—C13	1.535 (3)	C31—C32	1.416 (3)
C12—C17	1.550 (3)	C31—C37	1.420 (3)
C13—C14	1.562 (3)	C32—C33	1.363 (3)
C14—C15	1.531 (3)	C34—C35	1.364 (4)
C15—C16	1.545 (3)	C35—C36	1.408 (4)
C16—C17	1.580 (3)	C36—C37	1.365 (4)

C2—C1—C6	120.4 (2)	C20—C21—C22	102.95 (17)
C1—C2—C3	120.3 (2)	C20—C21—C23	122.72 (18)
C2—C3—C4	120.7 (2)	C22—C21—C23	102.85 (17)
C3—C4—C5	119.1 (2)	C18—C22—C21	103.20 (17)
C3—C4—C7	122.6 (2)	C18—C22—C24	123.41 (18)
C5—C4—C7	118.3 (2)	C21—C22—C24	102.85 (16)
C4—C5—C6	118.4 (2)	C21—C23—C26	113.65 (18)
C4—C5—C10	118.8 (2)	C21—C23—C27	100.81 (16)
C6—C5—C10	122.7 (2)	C26—C23—C27	99.68 (18)
C5—C6—C1	121.0 (2)	C22—C24—C25	114.65 (19)
C4—C7—C8	121.2 (2)	C22—C24—C27	100.62 (17)
C7—C8—C9	121.3 (2)	C25—C24—C27	99.23 (17)
C8—C9—C10	118.0 (2)	C24—C25—C26	103.21 (18)
C8—C9—C11	121.1 (2)	C23—C26—C25	103.04 (17)
C10—C9—C11	120.7 (2)	C23—C27—C24	93.55 (17)
C5—C10—C9	122.4 (2)	C23—C27—C28	118.46 (19)
C9—C11—C12	119.44 (18)	C24—C27—C28	117.74 (18)
C9—C11—C15	118.04 (18)	C27—C28—C29	122.4 (2)
C12—C11—C15	93.27 (16)	C27—C28—C33	119.7 (2)
C11—C12—C13	99.73 (18)	C29—C28—C33	117.7 (2)
C11—C12—C17	100.98 (17)	C28—C29—C30	122.2 (2)
C13—C12—C17	113.39 (17)	C29—C30—C31	119.0 (2)
C12—C13—C14	103.27 (18)	C29—C30—C34	122.1 (2)
C13—C14—C15	102.96 (18)	C31—C30—C34	118.9 (2)
C14—C15—C11	99.77 (18)	C30—C31—C32	118.3 (2)
C14—C15—C16	114.65 (18)	C30—C31—C37	118.8 (2)
C11—C15—C16	100.76 (17)	C32—C31—C37	122.9 (2)
C15—C16—C17	102.56 (16)	C31—C32—C33	120.9 (2)
C15—C16—C20	122.89 (18)	C28—C33—C32	121.9 (2)
C17—C16—C20	102.65 (17)	C30—C34—C35	120.8 (2)
C12—C17—C16	102.74 (17)	C34—C35—C36	120.5 (2)
C12—C17—C18	122.80 (18)	C35—C36—C37	120.4 (2)
C16—C17—C18	103.31 (16)	C31—C37—C36	120.6 (2)
C17—C18—C19	102.78 (17)	Cl3—C38—Cl1	110.8 (3)
C17—C18—C22	104.64 (17)	Cl3—C38—Cl2	109.7 (3)
C19—C18—C22	101.88 (17)	Cl1—C38—Cl2	113.8 (3)
C18—C19—C20	95.48 (17)	Cl5—C381—Cl4	105.6 (7)
C19—C20—C16	102.68 (17)	Cl5—C381—Cl6	114.0 (7)
C19—C20—C21	102.59 (17)	Cl4—C381—Cl6	118.6 (6)
C16—C20—C21	104.22 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C38—H381···Cg1	0.97	2.44	3.399	172.7
C381—H3811···Cg2	0.98	2.61	3.521	153.9

Acknowledgements

The authors acknowledge the donors of the American Chemical Society Petroleum Research Fund for financial support (to JMN) and the National Science Foundation (grant No. CHE-0521047, to BMF) for funding to support the purchase of an X-ray diffractometer. We thank Professor Matthew B. Zimmt of Brown University for valuable discussions.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Web of Science CrossRef IUCr Journals Google Scholar
Bodige, S. G., Sun, D., Marchand, A. P., Namboothiri, N. N., Shukla, R. & Watson, W. H. (1999). J. Chem. Crystallogr. 29, 523–530. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2006). APEXII. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chou, T.-C., Hwa, C.-L., Lin, J.-J., Liao, K.-C. & Tseng, J.-C. (2005). J. Org. Chem. 70, 9717–9726. Web of Science CSD CrossRef PubMed CAS Google Scholar
Klärner, F.-G., Panitzky, J., Bläser, D. & Boese, R. (2001). Tetrahedron, 57, 3673–3687. Google Scholar
Kurebayashi, H., Haino, T., Usui, S. & Fukazawa, Y. (2001). Tetrahedron, 57, 8667–8674. Web of Science CSD CrossRef CAS Google Scholar
Nadeau, J. M., Liu, M., Waldeck, D. H. & Zimmt, M. B. (2003). J. Am. Chem. Soc. 125, 15964–15973. Web of Science CrossRef PubMed CAS Google Scholar
Nemoto, H., Kawano, T., Ueji, N., Bando, M., Kido, M., Suzuki, I. & Shibuya, M. (2000). Org. Lett. 2, 1015–1017. Web of Science CrossRef PubMed CAS Google Scholar
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England. Google Scholar

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Volume 65| Part 10| October 2009| Pages o2427-o2428

doi:10.1107/S160053680903565X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

syn,syn-15,17-Di-2-naphthyl­hexa­cyclo­[10.2.1.13,10.15,8.02,11.04,9]hepta­decane deutero­chloro­form monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

syn,syn-15,17-Di-2-naphthylhexacyclo[10.2.1.1^3,10.1^5,8.0^2,11.0^4,9]heptadecane deuterochloroform monosolvate