Table 1 Crystal data and the structure refinement of the compounds 4a-d

Empirical formula

C₂₃ H₃₀ N₂

C₂₄ H₃₂ N₂

C₂₄ H₃₂ N₂ O

C₂₃ H₂₉ Cl N₂

Formula weight

334.49

348.52

364.52

368.93

Temperature (K)

198(2)

143(2)

88(2)

143(2)

Wavelength (Å)

0.71073

0.71073

0.71073

0.71073

Crystal system

Triclinic

Triclinic

Triclinic

Triclinic

Space group

P $\overline{1}$

P $\overline{1}$

P $\overline{1}$

P $\overline{1}$

Unit cell dimensions

a (Å)

9.6209(4)

8.9868(7)

9.4632(5)

8.8970(6)

b (Å)

11.0221(5)

10.3608(8)

10.3455(5)

10.3481(6)

c (Å)

11.0824(5)

12.0081(9)

12.0086(6)

11.9800(8)

α (^o)

112.2432(5)

98.8602(9)

92.8431(6)

98.9102(7)

β (^o)

97.8486(5)

106.9857(8)°

106.1653(5)

107.4484(6)

γ (^o)

102.1196(5)

93.2382(9)°

105.4519(6)

92.1628(7)

Volume (ų)

1032.76(8)

1050.44(14)

1078.59(9)

1035.36(12)

Z

2

2

2

2

Density (calculated) (Mg/m³)

1.076

1.102

1.122

1.183

Absorption coefficient (mm^-1)

0.062

0.064

0.068

0.193

F₀₀₀

364

380

396

396

Crystal size (mm³)

0.42 x 0.33 x 0.26

0.33 x 0.31 x 0.25

0.36 x 0.36 x 0.23

0.38 x 0.37 x 0.26

Theta range for data collection (^o)

2.04 to 26.37

1.80 to 28.40

1.78 to 28.82

1.81 to 28.54

Index ranges

−12 ≤ h ≤ 12, -13 ≤ k ≤ 13, -13 ≤ l ≤ 13

12 ≤ h ≤ 11, -13 ≤ k ≤ 13, -15 ≤ l ≤ 15

−12 ≤ h ≤ 12, -13 ≤ k ≤ 13, -15 ≤ l ≤ 16

−11 ≤ h ≤ 11, -13 ≤ k ≤ 13, -15 ≤ l ≤ 15

Reflections collected

11311

12098

13056

12115

Independent reflections

4202 [R(int) = 0.0142]

4779 [R(int) = 0.0145]

5172 [R(int) = 0.0138]

4753 [R(int) = 0.0172]

Refinement method

Full-matrix least-squares on F²

Full-matrix least-squares on F²

Full-matrix least-squares on F²

Full-matrix least-squares on F²

Completeness to theta = 25.50°

99.7%

99.6%

99.7%

99.6%

Max. and min. Transmission

0.9842 and 0.9742

0.9842 and 0.9794

0.9846 and 0.9760

0.9522 and 0.9295

Data / restraints / parameters

4202 / 0 / 251

4779 / 0 / 277

5172 / 0 / 255

4753 / 0 / 348

Goodness-of-fit on F²

1.049

1.037

1.072

1.049

Final R indices [I>2sigma(I)]

R1 = 0.0436, wR2 = 0.1186

R1 = 0.0438, wR2 = 0.1149

R1 = 0.0407, wR2 = 0.1089

R1 = 0.0366, wR2 = 0.0996

R indices (all data)

R1 = 0.0505, wR2 = 0.1248

R1 = 0.0535, wR2 = 0.1225

R1 = 0.0452, wR2 = 0.1126

R1 = 0.0406, wR2 = 0.1031

Largest diff. peak and hole (e.Å^-3)

0.264 and −0.197

0.264 and −0.201

0.328 and −0.325

0.328 and −0.225