Table 1 Crystal data and structure refinement parameters for compounds 1–3

Empirical formula

C₉H₁₁ClN₂O₅

C₉H₁₃ClN₂O₆

C₉H₁₂N₂O₅

Formula weight

262.65

280.66

228.21

Temperature (K)

293 (2)

293 (2)

293 (2)

Wavelength (Å)

1.54184

1.54184

0.71073

Crystal system

monoclinic

triclinic

monoclinic

Space group

P2₁ /c

P-1

P2₁ /c

Z

4

2

4

Unit cell dimensions

 a (Å)

8.402 (2)

7.019 (1)

6.211 (2)

 b (Å)

6.334 (1)

9.512 (2)

8.651 (3)

 c (Å)

22.023 (4)

9.740 (2)

19.594 (5)

 α (°)

90

79.19 (3)

90

 β (°)

100.72 (3)

88.58 (3)

91.27 (2)

 γ (°)

90

78.42 (3)

90

 V (ų)

1151.6 (4)

625.7 (2)

1052.6 (5)

 D _calc (g cm⁻³)

1.515

1.490

1.440

 μ (mm⁻¹)

3.099

2.950

0.119

 F (000)

544

292

480

Crystal size (mm)

0.22 × 0.14 × 0.07

0.15 × 0.12 × 0.08

0.35 × 0.4 × 0.6

θ range for data collection (°)

4.09–70.07

4.62–70.01

2.08–27.06

Limiting indices

− 10 ≤ h ≤ 1

− 8 ≤ h ≤ 8

0 ≤ h ≤ 7

− 7 ≤ k ≤ 0

− 4 ≤ k ≤ 11

0 ≤ k ≤ 11

− 26 ≤ l ≤ 26

− 11 ≤ l ≤ 11

− 25 ≤ l ≤ 25

Reflections collected/unique

2336/2192

2370/2370

2501/2294

Reflections with [I > 2σ(I)]

2010

2282

1761

Parameters

156

165

193

Goodness-of-fit on F²

1.007

1.003

1.001

R ₁, wR ₂ [I > 2σ(I)]

0.0384, 0.1128

0.0415, 0.1175

0.0371, 0.1023

R ₁, wR ₂ (all data)

0.0414, 0.1163

0.0424, 0.1187

0.0540, 0.11068

Largest difference in peak and hole (e Å⁻³)

0.330/− 0.311

0.385/− 0.315

0.265/− 0.212