Diethyl 3,4-bis-(acetoxymethyl)thieno[2,3-b]thiophene-2,5-dicarboxylate
B. Gunasekaran,
R. Sureshbabu,
A. K. Mohanakrishnan,
G. Chakkaravarthi,
V. Manivannan
Contact
V. Manivannan (manivan_1999@yahoo.com)
Department of Research and Development
PRIST University
Vallam
Thanjavur 613 403
Tamil Nadu
India
Structure (I):
Diethyl 3,4-bis-(acetoxymethyl)thieno[2,3-b]thiophene-2,5-dicarboxylate
Crystal data
| Formula: |
C18 H20 O8 S2 |
| Mr = |
428.46 |
| Cell: |
| triclinic |
P -1 |
| a = 9.3214(5) |
α = 84.952(3) |
| b = 10.2416(6) |
β = 82.814(4) |
| c = 10.6622(6) |
γ = 75.432(3) |
| V = 975.72(9) |
Z = 2 |
| Radiation: |
MoKα |
| μ = |
0.316 |
| T = |
295(2) |
| Crystal size: |
0.29
x 0.14
x 0.12 |
Data collection
| Device type: |
Bruker Kappa APEX2 CCD |
| Absorption correction: |
multi-scan / (SADABS; Sheldrick, 1996) |
| Tmin = 0.9138 |
Tmax = 0.9630 |
| Measured reflections: |
25739 |
| Independent reflections: |
6686 |
| Reflections with
I>2σ(I):
|
4444 |
| Rint = |
0.0248 |
Refinement
| R1 = |
0.0572 |
| wR2 = |
0.1883 |
| S = |
1.042 |
| Reflections: |
6686 |
| Parameters: |
279 |
| Restraints: |
4 |
| H treatment: |
constr |
| Δρmax = 0.819 |
Δρmin = -0.591 |
Geometry
Table 1. Atoms
| atom |
x |
y |
z |
Uiso or Ueq
|
ADP type |
calc. flag |
refinement type |
occ. |
disorder assembly |
disorder group |
| S1 |
0.02951(5) |
0.21624(6) |
0.28483(5) |
0.04706(15) |
Uani |
d |
. |
1 |
. |
. |
| S2 |
-0.08189(5) |
0.30619(5) |
0.55975(5) |
0.04537(15) |
Uani |
d |
. |
1 |
. |
. |
| O1 |
0.1876(2) |
0.1299(2) |
0.05271(17) |
0.0747(5) |
Uani |
d |
. |
1 |
A |
. |
| O2 |
0.4020(2) |
0.1825(3) |
0.0622(2) |
0.0920(7) |
Uani |
d |
. |
1 |
. |
. |
| O3 |
0.51977(16) |
0.15799(15) |
0.36366(18) |
0.0544(4) |
Uani |
d |
. |
1 |
. |
. |
| O4 |
0.70351(19) |
0.25297(19) |
0.3848(2) |
0.0719(5) |
Uani |
d |
. |
1 |
. |
. |
| O5 |
0.40617(17) |
0.27623(16) |
0.65075(16) |
0.0533(4) |
Uani |
d |
. |
1 |
. |
. |
| O6 |
0.5449(3) |
0.4048(2) |
0.7014(3) |
0.0978(8) |
Uani |
d |
. |
1 |
. |
. |
| O7 |
-0.1209(3) |
0.3926(2) |
0.80902(18) |
0.0821(6) |
Uani |
d |
. |
1 |
B |
. |
| O8 |
0.1045(3) |
0.4242(3) |
0.8232(2) |
0.1029(9) |
Uani |
d |
. |
1 |
. |
. |
| C1 |
0.2123(2) |
0.2247(2) |
0.2352(2) |
0.0483(5) |
Uani |
d |
. |
1 |
. |
. |
| C2 |
0.2772(2) |
0.2731(2) |
0.3227(2) |
0.0463(4) |
Uani |
d |
. |
1 |
. |
. |
| C3 |
0.1771(2) |
0.30467(19) |
0.4351(2) |
0.0424(4) |
Uani |
d |
. |
1 |
. |
. |
| C4 |
0.1817(2) |
0.3531(2) |
0.5561(2) |
0.0469(5) |
Uani |
d |
. |
1 |
. |
. |
| C5 |
0.0511(3) |
0.3560(2) |
0.6319(2) |
0.0483(5) |
Uani |
d |
. |
1 |
. |
. |
| C6 |
0.0398(2) |
0.2773(2) |
0.42631(19) |
0.0406(4) |
Uani |
d |
. |
1 |
. |
. |
| C7 |
0.2789(3) |
0.1791(3) |
0.1093(2) |
0.0592(6) |
Uani |
d |
. |
1 |
. |
. |
| C8 |
0.2451(5) |
0.0815(5) |
-0.0725(3) |
0.0994(12) |
Uani |
d |
D |
1 |
. |
. |
| H8A |
0.3523 |
0.0700 |
-0.0854 |
0.119 |
Uiso |
calc |
PR |
0.368(18) |
A |
1 |
| H8B |
0.2009 |
0.1469 |
-0.1369 |
0.119 |
Uiso |
calc |
PR |
0.368(18) |
A |
1 |
| H8C |
0.2708 |
0.1540 |
-0.1285 |
0.119 |
Uiso |
d |
PR |
0.632(18) |
A |
2 |
| H8D |
0.3340 |
0.0087 |
-0.0667 |
0.119 |
Uiso |
d |
PR |
0.632(18) |
A |
2 |
| C9 |
0.208(3) |
-0.0509(13) |
-0.0829(17) |
0.148(7) |
Uani |
d |
PD |
0.368(18) |
A |
1 |
| H9A |
0.1181 |
-0.0543 |
-0.0286 |
0.223 |
Uiso |
calc |
PR |
0.368(18) |
A |
1 |
| H9B |
0.2880 |
-0.1235 |
-0.0579 |
0.223 |
Uiso |
calc |
PR |
0.368(18) |
A |
1 |
| H9C |
0.1924 |
-0.0595 |
-0.1689 |
0.223 |
Uiso |
calc |
PR |
0.368(18) |
A |
1 |
| C9A |
0.1272(9) |
0.0290(14) |
-0.1206(8) |
0.112(4) |
Uani |
d |
PD |
0.632(18) |
A |
2 |
| H9A1 |
0.1651 |
-0.0102 |
-0.2003 |
0.168 |
Uiso |
calc |
PR |
0.632(18) |
A |
2 |
| H9A2 |
0.0413 |
0.1020 |
-0.1316 |
0.168 |
Uiso |
calc |
PR |
0.632(18) |
A |
2 |
| H9A3 |
0.0998 |
-0.0385 |
-0.0606 |
0.168 |
Uiso |
calc |
PR |
0.632(18) |
A |
2 |
| C10 |
0.4373(2) |
0.2825(2) |
0.3058(3) |
0.0538(5) |
Uani |
d |
. |
1 |
. |
. |
| H10A |
0.4724 |
0.2915 |
0.2167 |
0.065 |
Uiso |
calc |
R |
1 |
. |
. |
| H10B |
0.4480 |
0.3596 |
0.3472 |
0.065 |
Uiso |
calc |
R |
1 |
. |
. |
| C11 |
0.6524(2) |
0.1574(2) |
0.3979(2) |
0.0457(4) |
Uani |
d |
. |
1 |
. |
. |
| C12 |
0.7265(3) |
0.0225(3) |
0.4536(3) |
0.0755(8) |
Uani |
d |
. |
1 |
. |
. |
| H12A |
0.7131 |
-0.0469 |
0.4044 |
0.113 |
Uiso |
calc |
R |
1 |
. |
. |
| H12B |
0.6830 |
0.0110 |
0.5391 |
0.113 |
Uiso |
calc |
R |
1 |
. |
. |
| H12C |
0.8310 |
0.0164 |
0.4532 |
0.113 |
Uiso |
calc |
R |
1 |
. |
. |
| C13 |
0.3113(3) |
0.3958(2) |
0.5957(3) |
0.0562(6) |
Uani |
d |
. |
1 |
. |
. |
| H13A |
0.3653 |
0.4326 |
0.5231 |
0.067 |
Uiso |
calc |
R |
1 |
. |
. |
| H13B |
0.2769 |
0.4644 |
0.6572 |
0.067 |
Uiso |
calc |
R |
1 |
. |
. |
| C14 |
0.5192(2) |
0.2971(2) |
0.7048(2) |
0.0508(5) |
Uani |
d |
. |
1 |
. |
. |
| C15 |
0.6043(3) |
0.1712(3) |
0.7674(3) |
0.0684(7) |
Uani |
d |
. |
1 |
. |
. |
| H15A |
0.7092 |
0.1640 |
0.7472 |
0.103 |
Uiso |
calc |
R |
1 |
. |
. |
| H15B |
0.5792 |
0.0946 |
0.7381 |
0.103 |
Uiso |
calc |
R |
1 |
. |
. |
| H15C |
0.5796 |
0.1736 |
0.8575 |
0.103 |
Uiso |
calc |
R |
1 |
. |
. |
| C16 |
0.0166(4) |
0.3957(3) |
0.7634(2) |
0.0638(6) |
Uani |
d |
. |
1 |
. |
. |
| C17 |
-0.1557(5) |
0.4318(5) |
0.9381(3) |
0.1211(17) |
Uani |
d |
D |
1 |
. |
. |
| H17A |
-0.1449 |
0.5229 |
0.9429 |
0.145 |
Uiso |
calc |
PR |
0.368(18) |
A |
1 |
| H17B |
-0.0876 |
0.3714 |
0.9916 |
0.145 |
Uiso |
calc |
PR |
0.368(18) |
A |
1 |
| H17C |
-0.0621 |
0.4205 |
0.9736 |
0.145 |
Uiso |
d |
PR |
0.632(18) |
A |
2 |
| H17D |
-0.2071 |
0.5267 |
0.9393 |
0.145 |
Uiso |
d |
PR |
0.632(18) |
A |
2 |
| C18 |
-0.3127(7) |
0.4253(12) |
0.9829(7) |
0.097(3) |
Uani |
d |
PD |
0.623(17) |
B |
1 |
| H18A |
-0.3228 |
0.3352 |
0.9769 |
0.146 |
Uiso |
calc |
PR |
0.623(17) |
B |
1 |
| H18B |
-0.3796 |
0.4871 |
0.9311 |
0.146 |
Uiso |
calc |
PR |
0.623(17) |
B |
1 |
| H18C |
-0.3361 |
0.4495 |
1.0693 |
0.146 |
Uiso |
calc |
PR |
0.623(17) |
B |
1 |
| C18A |
-0.238(2) |
0.3432(15) |
1.0223(10) |
0.107(5) |
Uani |
d |
PD |
0.377(17) |
B |
2 |
| H18D |
-0.2882 |
0.3907 |
1.0951 |
0.161 |
Uiso |
calc |
PR |
0.377(17) |
B |
2 |
| H18E |
-0.1680 |
0.2625 |
1.0491 |
0.161 |
Uiso |
calc |
PR |
0.377(17) |
B |
2 |
| H18F |
-0.3090 |
0.3197 |
0.9766 |
0.161 |
Uiso |
calc |
PR |
0.377(17) |
B |
2 |
Table 2. Selected Bonds
| bond |
distance |
| S1 - C6 |
1.705(2) |
| S1 - C1 |
1.741(2) |
| S2 - C6 |
1.703(2) |
| S2 - C5 |
1.736(2) |
| O1 - C7 |
1.319(3) |
| O1 - C8 |
1.455(3) |
| O2 - C7 |
1.200(3) |
| O3 - C11 |
1.331(2) |
| O3 - C10 |
1.443(3) |
| O4 - C11 |
1.183(3) |
| O5 - C14 |
1.332(2) |
| O5 - C13 |
1.444(3) |
| O6 - C14 |
1.182(3) |
| O7 - C16 |
1.320(4) |
| O7 - C17 |
1.443(4) |
| O8 - C16 |
1.203(3) |
| C1 - C2 |
1.362(3) |
| C1 - C7 |
1.471(3) |
| C2 - C3 |
1.431(3) |
| C2 - C10 |
1.507(3) |
| C3 - C6 |
1.393(2) |
| C3 - C4 |
1.431(3) |
| C4 - C5 |
1.369(3) |
| C4 - C13 |
1.503(3) |
| C5 - C16 |
1.469(3) |
| C8 - C9A |
1.4988(10) |
| C8 - C9 |
1.4994(10) |
| C8 - H8A |
0.9700 |
| C8 - H8B |
0.9700 |
| C8 - H8C |
0.9700 |
| C8 - H8D |
0.9700 |
| C9 - H9A |
0.9600 |
| C9 - H9B |
0.9600 |
| C9 - H9C |
0.9600 |
| C9A - H9A1 |
0.9600 |
| C9A - H9A2 |
0.9600 |
| C9A - H9A3 |
0.9600 |
| C10 - H10A |
0.9700 |
| C10 - H10B |
0.9700 |
| C11 - C12 |
1.489(3) |
| C12 - H12A |
0.9600 |
| C12 - H12B |
0.9600 |
| C12 - H12C |
0.9600 |
| C13 - H13A |
0.9700 |
| C13 - H13B |
0.9700 |
| C14 - C15 |
1.485(3) |
| C15 - H15A |
0.9600 |
| C15 - H15B |
0.9600 |
| C15 - H15C |
0.9600 |
| C17 - C18 |
1.4972(10) |
| C17 - C18A |
1.4987(10) |
| C17 - H17A |
0.9700 |
| C17 - H17B |
0.9700 |
| C17 - H17C |
0.9700 |
| C17 - H17D |
0.9700 |
| C18 - H18A |
0.9600 |
| C18 - H18B |
0.9600 |
| C18 - H18C |
0.9600 |
| C18A - H18D |
0.9600 |
| C18A - H18E |
0.9600 |
| C18A - H18F |
0.9600 |
Table 3. Selected Angles
| bonds |
angle |
| C6
- S1 -
C1 |
90.24(10) |
| C6
- S2 -
C5 |
89.62(10) |
| C7
- O1 -
C8 |
115.4(2) |
| C11
- O3 -
C10 |
117.10(16) |
| C14
- O5 -
C13 |
115.27(17) |
| C16
- O7 -
C17 |
112.2(3) |
| C2
- C1 -
C7 |
127.8(2) |
| C2
- C1 -
S1 |
113.60(17) |
| C7
- C1 -
S1 |
118.60(17) |
| C1
- C2 -
C3 |
111.29(17) |
| C1
- C2 -
C10 |
123.9(2) |
| C3
- C2 -
C10 |
124.7(2) |
| C6
- C3 -
C4 |
111.15(19) |
| C6
- C3 -
C2 |
111.75(18) |
| C4
- C3 -
C2 |
137.07(18) |
| C5
- C4 -
C3 |
110.97(17) |
| C5
- C4 -
C13 |
124.0(2) |
| C3
- C4 -
C13 |
125.0(2) |
| C4
- C5 -
C16 |
126.5(2) |
| C4
- C5 -
S2 |
114.14(16) |
| C16
- C5 -
S2 |
119.35(19) |
| C3
- C6 -
S2 |
114.09(15) |
| C3
- C6 -
S1 |
113.12(15) |
| S2
- C6 -
S1 |
132.76(11) |
| O2
- C7 -
O1 |
122.8(3) |
| O2
- C7 -
C1 |
125.5(3) |
| O1
- C7 -
C1 |
111.7(2) |
| O1
- C8 -
C9A |
107.7(3) |
| O1
- C8 -
C9 |
108.9(7) |
| O1
- C8 -
H8A |
109.9 |
| C9A
- C8 -
H8A |
139.2 |
| C9
- C8 -
H8A |
109.9 |
| O1
- C8 -
H8B |
109.9 |
| C9A
- C8 -
H8B |
72.5 |
| C9
- C8 -
H8B |
109.9 |
| H8A
- C8 -
H8B |
108.3 |
| O1
- C8 -
H8C |
110.2 |
| C9A
- C8 -
H8C |
111.5 |
| C9
- C8 -
H8C |
138.2 |
| H8A
- C8 -
H8C |
69.4 |
| O1
- C8 -
H8D |
109.8 |
| C9A
- C8 -
H8D |
109.2 |
| C9
- C8 -
H8D |
70.6 |
| H8B
- C8 -
H8D |
137.3 |
| H8C
- C8 -
H8D |
108.5 |
| C8
- C9 -
H9A |
109.5 |
| H8D
- C9 -
H9A |
131.3 |
| C8
- C9 -
H9B |
109.5 |
| H8D
- C9 -
H9B |
72.5 |
| C8
- C9 -
H9C |
109.5 |
| H8D
- C9 -
H9C |
115.5 |
| C8
- C9A -
H9A1 |
109.5 |
| C8
- C9A -
H9A2 |
109.5 |
| H9A1
- C9A -
H9A2 |
109.5 |
| C8
- C9A -
H9A3 |
109.5 |
| H9A1
- C9A -
H9A3 |
109.5 |
| H9A2
- C9A -
H9A3 |
109.5 |
| O3
- C10 -
C2 |
105.38(16) |
| O3
- C10 -
H10A |
110.7 |
| C2
- C10 -
H10A |
110.7 |
| O3
- C10 -
H10B |
110.7 |
| C2
- C10 -
H10B |
110.7 |
| H10A
- C10 -
H10B |
108.8 |
| O4
- C11 -
O3 |
123.4(2) |
| O4
- C11 -
C12 |
125.0(2) |
| O3
- C11 -
C12 |
111.5(2) |
| C11
- C12 -
H12A |
109.5 |
| C11
- C12 -
H12B |
109.5 |
| H12A
- C12 -
H12B |
109.5 |
| C11
- C12 -
H12C |
109.5 |
| H12A
- C12 -
H12C |
109.5 |
| H12B
- C12 -
H12C |
109.5 |
| O5
- C13 -
C4 |
106.55(16) |
| O5
- C13 -
H13A |
110.4 |
| C4
- C13 -
H13A |
110.4 |
| O5
- C13 -
H13B |
110.4 |
| C4
- C13 -
H13B |
110.4 |
| H13A
- C13 -
H13B |
108.6 |
| O6
- C14 -
O5 |
122.2(2) |
| O6
- C14 -
C15 |
125.9(2) |
| O5
- C14 -
C15 |
111.9(2) |
| C14
- C15 -
H15A |
109.5 |
| C14
- C15 -
H15B |
109.5 |
| H15A
- C15 -
H15B |
109.5 |
| C14
- C15 -
H15C |
109.5 |
| H15A
- C15 -
H15C |
109.5 |
| H15B
- C15 -
H15C |
109.5 |
| O8
- C16 -
O7 |
124.1(3) |
| O8
- C16 -
C5 |
124.0(3) |
| O7
- C16 -
C5 |
111.9(2) |
| O7
- C17 -
C18 |
108.9(3) |
| O7
- C17 -
C18A |
113.7(5) |
| O7
- C17 -
H17A |
109.9 |
| C18
- C17 -
H17A |
109.9 |
| C18A
- C17 -
H17A |
133.7 |
| O7
- C17 -
H17B |
109.9 |
| C18
- C17 -
H17B |
109.9 |
| C18A
- C17 -
H17B |
70.5 |
| H17A
- C17 -
H17B |
108.3 |
| O7
- C17 -
H17C |
107.6 |
| C18
- C17 -
H17C |
138.3 |
| C18A
- C17 -
H17C |
105.0 |
| H17A
- C17 -
H17C |
75.1 |
| O7
- C17 -
H17D |
109.6 |
| C18
- C17 -
H17D |
78.0 |
| C18A
- C17 -
H17D |
112.7 |
| H17B
- C17 -
H17D |
134.0 |
| H17C
- C17 -
H17D |
107.8 |
| C17
- C18 -
H18A |
109.5 |
| C17
- C18 -
H18B |
109.5 |
| C17
- C18 -
H18C |
109.5 |
| C17
- C18A -
H18D |
109.5 |
| C17
- C18A -
H18E |
109.5 |
| H18D
- C18A -
H18E |
109.5 |
| C17
- C18A -
H18F |
109.5 |
| H18D
- C18A -
H18F |
109.5 |
| H18E
- C18A -
H18F |
109.5 |