syn,syn-15,17-Di-2-naphthyl-hexa-cyclo-[10.2.1.1.1.0.0]hepta-decane deuterochloro-form monosolvate.

The main molecule of the title compound, C(37)H(36)·CDCl(3), is a hydro-carbon 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 mol-ecule (CDCl(3)) in the cleft. The CDCl(3) solvent mol-ecule is present in two disordered orientations in a 3:2 ratio, each involving C-D⋯π to C(6) 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 = 600.07

Triclinic,

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[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.162

S = 1.00

5889 reflections

505 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.56 e Å−3

Δρmin = −0.83 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C38H37Cl3	Z = 2
Mr = 600.07	F(000) = 632
Triclinic, P1	Dx = 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

Area diffractometer	5889 independent reflections
Radiation source: fine-focus sealed tube	4451 reflections with I > 2.0σ(I)
graphite	Rint = 0.074
φ and ω scans	θmax = 26.4°, θmin = 1.4°
Absorption correction: multi-scan (APEX2; Bruker, 2006)	h = −7→7
Tmin = 0.90, Tmax = 0.92	k = −18→18
18141 measured reflections	l = −20→20

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(Fo2,0) + 2Fc2)/3
5889 reflections	(Δ/σ)max = 0.005
505 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.83 e Å−3
0 constraints

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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

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

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 and

Cg2 is the centroid of the C4–C10 ring.