Crystallography of 15. The crystal, a colorless block, was obtained from sublimation. The
crystal data for 15 are as follows: monoclinic, space group P21/c with a = 9.2959(16) Å, b =
12.951(2) Å, c = 10.2700(14) Å; = 92.549(13)°, volume = 1235.2(4) Å3, and Z = 4. The
empirical formula is C16H24, the formula weight is 216.4, and the calculated density is 1.163
g/cm3. The X-ray data were collected by use of CuKradiation ( = 1.54178 Å) on a
Siemens P4 diffractometer. The refinement was performed using a full-matrix least squares
procedure. The agreement factors are R = 0.0567 and Rw = 0.08 for 1417 reflections out of
1664 independent reflections.
Table 1 Structure Determination Summary for 15. Crystal Data
Empirical Formula
C16H24
Color; Habit
colorless block
Crystal Size (mm)
Crystal System
Space Group
0.4 x 0.5 x 0.5
Monoclinic
P21/c
a = 9.2959(16) Å
b = 12.951(2) Å
c = 10.2700(14) Å
β = 92.549(13)
1235.2(4) Å3
Unit Cell Dimensions
Volume
Peaks to determine cell
2-theta range of cell peaks
Z
Formula weight
Density (calc.)
Absorption Coefficient
F(000)
Data Collection
Diffractometer Used
Radiation
Temperature
Monochromator
2 Range
Scan Type
Scan Speed
41
20.0 to 55.00°
4
216.4
1.163 g/cm3
0.441 mm-1
480
Siemens P4
CuK ( = 1.54178 Å)
-160(2)°C 113(2) K
Highly oriented graphite crystal
4.0 to 114.0°
2
Variable; 4.00 to 30.00°/min.
in 
Scan Range (
Background Measurements
scan time
Standard Reflections
° plus -separation
Stationary crystal and stationary counter at
beginning and
end of scan, each for 20.0% of total
(1, 0, 4)
(0, 2,2)
(2, 1, 1)
measured every 50 reflections
with a maximum variation of .04
-1 ≤ h ≤10, -1 ≤ k ≤ 14
-11 ≤ l ≤ 11
2229
1664 (Rint = 4.36 %)
1417 (F > 4.0(F))
N/A
Index Ranges
Reflections Collected
Independent Reflections
Observed Reflections
Absorptions Correction
Solution and Refinement
System Used
Solution
Siemens SHELXTL PLUS(SGI)
Direct Methods
Refinement Method
Quantity Minimized
Full-Matrix Least-Squares
w(Fo-Fc)2
Extinction Correction
Hydrogen Atoms
Weighting Scheme
Number of Parameters refined
Final R indices (obs. data)
R indices (all data)
Goodness-of-Fit
N/A
Riding model, isotropic U
w-1 = 2(F) + 0.0010F2
146
R = 5.67 %, wR = 8.00 %
R = 6.42 %, wR = 8.27 %
1.70
Largest and Mean /
Data-to-Parameter Ratio
Largest Difference Peak
0.001, 0.000
9.7:1
0.30 eÅ-3
Largest Difference Hole
-0.24 eÅ-3
Table 2 Atomic coordinates (x105) and equivalent isotropic displacement
coefficients (Å x 104) for 15.
x
C(1a)
5707(3)
C(2a)
7050(3)
C(3a)
6867(3)
C(4a)
6683(3)
C(5a)
6700(3)
C(6a)
5520(3)
C(7a)
8351(3)
C(8a)
8152(3)
C(1b)
–1045(2)
C(2b)
–2340(3)
C(3b)
–3484(3)
C(4b)
–2908(3)
C(5b)
–1312(3)
C(6b)
–509(3)
C(7b)
–1879(3)
C(8b)
–1154(3)
y
3629(2)
3084(2)
2910(2)
3954(2)
4837(2)
4663(2)
3776(2)
4819(2)
–1230(2)
–1732(2)
–913(2)
–104(2)
–288(2)
–330(2)
–2188(2)
–1352(2)
z
–521(2)
46(2)
1498(2)
2184(2)
1187(2)
149(2)
–134(3)
546(2)
–696(2)
–103(2)
95(2)
1075(3)
1398(2)
157(2)
1231(2)
2080(3)
U(eq)
234(8)
226(8)
280(9)
253(8)
201(7)
170(7)
275(8)
253(8)
231(8)
223(8)
239(8)
352(9)
263(8)
169(7)
277(9)
363(9)
* Equivalent isotropic U defined as one third of the trace orthogonalized
Table 3. Bond lengths (Å) for 15.
C(1a)–C(2a)
1.527(3)
C(2a)–C(3a)
1.526(3)
C(3a)–C(4a)
1.537(3)
C(5a)–C(6a)
1.512(3)
C(6a)–C(6aa)
1.328(5)
C(1b)–C(2b)
1.520(3)
C(2b)–C(3b)
1.522(3)
C(3b)–C(4b)
1.533(4)
C(5b)–C(6b)
1.506(3)
C(6b)–C(6ba) 1.326(5)
C(1a)–C(6a)
C(2a)–C(7a)
C(4a)–C(5a)
C(5a)–C(8a)
C(7a)–C(8a)
C(1b)–C(6b)
C(2b)–C(7b)
C(4b)–C(5b)
C(5b)–C(8b)
C(7b)–C(8b)
Table 4. Bond angles (°) for 15
C(2a)–C(1a)–C(6a) 110.1(2)
C(1a)–C(2a)–C(7a) 108.8(2)
C(2a)–C(3a)–C(4a) 109.7(2)
C(4a)–C(5a)–C(6a) 109.3(2)
C(6a)–C(5a)–C(8a) 108.7(2)
C(1a)–C(6a)–C(6aa) 124.8(3)
C(2a)–C(7a)–C(8a) 110.5(2)
C(2b)–C(1b)–C(6b) 109.9(2)
C(1b)–C(2b)–C(7b) 109.1(2)
C(2b)–C(3b)–C(4b) 109.8(2)
C(1a)–C(2a)–C(3a)
C(3a)–C(2a)–C(7a)
C(3a)–C(4a)–C(5a)
C(4a)–C(5a)–C(8a)
C(1a)–C(6a)–C(5a)
C(5a)–C(6a)–C(6aa)
C(5a)–C(8a)–C(7a)
C(1b)–C(2b)–C(3b)
C(3b)–C(2b)–C(7b)
C(3b)–C(4b)–C(5b)
1.520(3)
1.523(3)
1.536(3)
1.528(3)
1.535(3)
1.529(3)
1.535(3)
1.524(4)
1.550(4)
1.528(4)
108.4(2)
109.3(2)
110.2(2)
108.2(2)
110.9(2)
124.3(3)
109.7(2)
109.0(2)
108.6(2)
110.2(2)
Uij tensor
C(4b)–C(5b)–C(6b)
C(6b)–C(5b)–C(8b)
C(1b)–C(6b)–C(6ba)
C(2b)–C(7b)–C(8b)
109.6(2)
108.0(2)
124.7(3)
109.6(2)
C(4b)–C(5b)–C(8b)
C(1b)–C(6b)–C(5b)
C(5b)–C(6b)–C(6ba)
C(5b)–C(8b)–C(7b)
108.0(2)
110.6(2)
124.7(3)
110.0(2)
Table 5. Anisotropic displacement coefficients (Å2x103) for 15.
U(11)
U(22)
U(33)
U(12)
U(13)
U(23)
C(1a)
212(14) 192(13) 295(14)
12(10) –29(10) –12(11)
C(2a)
257(14) 169(13) 253(14)
48(11)
11(10) –21(11)
C(3a)
364(16) 205(14) 272(15)
–7(11)
13(11)
56(11)
C(4a)
229(14) 309(16) 220(13)
25(11)
3(10) –14(11)
C(5a)
201(13) 181(13) 216(13)
1(10) –53(10) –28(10)
C(6a)
174(12) 164(12) 171(12)
–4(9)
2(9)
9(9)
C(7a)
219(13) 317(15) 290(15)
24(12)
27(11)
64(12)
C(8a)
224(14) 231(14) 299(15) –35(11) –51(11)
45(11)
C(1b)
184(13) 192(13) 319(14) –11(10)
31(10) –57(11)
C(2b)
193(14) 210(14) 266(14) –50(10)
12(10) –78(11)
C(3b)
193(13) 237(14) 287(14)
5(11)
26(10)
48(11)
C(4b)
275(15) 253(15) 545(18) –54(12) 192(13) –131(13)
C(5b)
256(15) 289(15) 247(14) –119(11)
37(11) –102(11)
C(6b)
173(12) 145(12) 188(12)
6(9)
–8(9)
–13(9)
C(7b)
268(15) 219(14) 344(16)
–9(11)
7(12)
45(11)
C(8b)
400(17) 444(17) 243(14) –143(14)
-22(12)
48(13)
Table 6 Hydrogen-atom coordinates (x 104) and equivalent isotropic displacement
coefficients (Å2 x 103) for 15.
x
y
z
U(eq)
H(1aa)
5795
3734
–1439
355(16)
H(1ab)
4876
3206
–401
355(16)
H(2aa)
7177
2436
–386
355(16)
H(3aa)
6037
2485
1620
355(16)
H(3ab)
7696
2559
1871
355(16)
H(4aa)
5787
3960
2615
355(16)
H(4ab)
7449
4049
2831
355(16)
H(5aa)
6565
5488
1613
355(16)
H(7aa)
9202
3443
224
355(16)
H(7ab)
8473
3886
–1047
355(16)
H(8aa)
8914
4922
1194
355(16)
H(8ab)
8191
5367
–81
355(16)
H(1ba)
–290
–1730
–768
355(16)
H(1bb)
–1309
–983
–1556
355(16)
H(2ba)
–2720
–2266
–668
355(16)
H(3ba)
–4333
–1230
414
355(16)
H(3bb)
–3739
–586
–722
355(16)
H(4ba)
–3042
574
714
355(16)
H(4bb)
H(5ba)
H(7ba)
H(7bb)
H(8ba)
H(8bb)
–3433
–929
–1220
–2706
–1591
–152
–145
248
–2749
–2452
–1328
–1513
1858
1957
1118
1649
2909
2229
355(16)
355(16)
355(16)
355(16)
355(16)
355(16)