11

Table 1 Crystal data and structure refinement for 11.
Identification code	11
Empirical formula	C₁₁H₉N₃O₄S
Formula weight	279.27
Temperature/K	294.37(10)
Crystal system	monoclinic
Space group	Pn
a/Å	6.7057(2)
b/Å	4.7543(2)
c/Å	17.7050(6)
α/°	90
β/°	95.298(3)
γ/°	90
Volume/Å³	562.04(3)
Z	2
ρ_calcg/cm³	1.650
μ/mm^‑1	2.740
F(000)	288.0
Crystal size/mm³	0.3 × 0.2 × 0.02
Radiation	Cu Kα (λ = 1.54184)
2Θ range for data collection/°	10.034 to 152.168
Index ranges	-8 ≤ h ≤ 7, -5 ≤ k ≤ 5, -21 ≤ l ≤ 19
Reflections collected	1983
Independent reflections	1499 [R_int = 0.0259, R_sigma = 0.0518]
Data/restraints/parameters	1499/2/176
Goodness-of-fit on F²	1.049
Final R indexes [I>=2σ (I)]	R₁ = 0.0343, wR₂ = 0.0815
Final R indexes [all data]	R₁ = 0.0358, wR₂ = 0.0833
Largest diff. peak/hole / e Å^-3	0.28/-0.19
Flack parameter	-0.02(3)

Table 2 Fractional Atomic Coordinates (×10⁴) and Equivalent Isotropic Displacement Parameters (Å²×10³) for 11. U_eq is defined as 1/3 of of the trace of the orthogonalised U_IJ tensor.
Atom	x	y	z	U(eq)
S11	5963.3(10)	3490.3(19)	4122.7(6)	32.7(2)
O1	6092(4)	9890(6)	5984.0(16)	34.2(6)
O2	7518(4)	6811(7)	5279.0(19)	46.1(8)
O3	6644(4)	13645(7)	7086.5(17)	41.6(7)
N14	2275(5)	4989(7)	3941.3(18)	34.2(7)
O4	9026(5)	-778(8)	3466(2)	52.9(8)
N16	4943(6)	120(8)	2917(2)	42.0(8)
C2	5996(5)	7972(8)	5410(2)	32.9(7)
N13	2503(5)	3037(7)	3380.0(19)	35.7(7)
C8	4755(5)	13383(8)	6739(2)	31.9(7)
C3	4024(5)	7484(8)	4993(2)	30.2(7)
C12	4335(5)	2041(8)	3404(2)	32.3(8)
C10	2568(5)	10964(8)	5779(2)	30.9(7)
C9	4459(5)	11393(8)	6162(2)	30.4(7)
C15	3914(5)	5473(8)	4368(2)	29.1(7)
C6	1247(6)	14559(9)	6545(2)	37.1(8)
C4	2406(5)	8886(8)	5191(2)	32.2(7)
C7	3139(6)	14958(9)	6922(2)	37.0(8)
C5	955(6)	12587(9)	5981(2)	35.4(8)

Table 2 Fractional Atomic Coordinates (×10⁴) and Equivalent Isotropic Displacement Parameters (Å²×10³) for 11. U_eq is defined as 1/3 of of the trace of the orthogonalised U_IJ tensor.

Atom

U(eq)

S11

5963.3(10)

3490.3(19)

4122.7(6)

32.7(2)

6092(4)

9890(6)

5984.0(16)

34.2(6)

7518(4)

6811(7)

5279.0(19)

46.1(8)

6644(4)

13645(7)

7086.5(17)

41.6(7)

N14

2275(5)

4989(7)

3941.3(18)

34.2(7)

9026(5)

-778(8)

3466(2)

52.9(8)

N16

4943(6)

120(8)

2917(2)

42.0(8)

5996(5)

7972(8)

5410(2)

32.9(7)

N13

2503(5)

3037(7)

3380.0(19)

35.7(7)

4755(5)

13383(8)

6739(2)

31.9(7)

4024(5)

7484(8)

4993(2)

30.2(7)

C12

4335(5)

2041(8)

3404(2)

32.3(8)

C10

2568(5)

10964(8)

5779(2)

30.9(7)

4459(5)

11393(8)

6162(2)

30.4(7)

C15

3914(5)

5473(8)

4368(2)

29.1(7)

1247(6)

14559(9)

6545(2)

37.1(8)

2406(5)

8886(8)

5191(2)

32.2(7)

3139(6)

14958(9)

6922(2)

37.0(8)

955(6)

12587(9)

5981(2)

35.4(8)

Table 3 Anisotropic Displacement Parameters (Å²×10³) for 11. The Anisotropic displacement factor exponent takes the form: -2π²[h²a*²U₁₁+2hka*b*U₁₂+…].
Atom	U₁₁	U₂₂	U₃₃	U₂₃	U₁₃	U₁₂
S11	29.1(4)	34.7(4)	33.6(4)	-3.1(4)	-1.4(3)	0.0(4)
O1	26.7(12)	38.6(15)	36.2(13)	-7.5(12)	-2.8(10)	1.5(10)
O2	32.0(14)	52.6(18)	52.3(18)	-15.2(15)	-3.6(13)	7.7(13)
O3	36.7(15)	50.3(17)	35.8(14)	-10.9(13)	-7.0(12)	0.7(12)
N14	34.9(16)	33.7(16)	32.8(15)	-3.9(14)	-3.2(13)	3.0(12)
O4	38.5(16)	54(2)	65(2)	-0.2(18)	-2.6(15)	0.0(14)
N16	43.3(18)	42.1(17)	39.8(17)	-10.9(17)	0.2(14)	0.8(15)
C2	29.6(17)	35.2(18)	33.4(17)	-0.6(15)	-0.4(14)	1.3(14)
N13	36.1(16)	38.4(17)	31.2(15)	-4.1(14)	-4.4(12)	1.5(13)
C8	29.8(17)	38.1(19)	27.1(16)	2.3(15)	-0.9(13)	-4.3(15)
C3	31.5(17)	30.4(18)	27.9(15)	2.9(14)	-1.6(13)	-3.2(13)
C12	34.5(18)	32.5(18)	29.2(17)	1.4(15)	-0.1(14)	-3.6(14)
C10	29.8(17)	31.8(18)	30.6(17)	3.5(14)	0.4(13)	-1.2(13)
C9	28.8(16)	32.2(18)	29.8(16)	3.3(14)	-0.2(13)	-0.6(13)
C15	28.4(16)	28.2(16)	30.2(16)	6.1(14)	-0.4(13)	3.1(13)
C6	35.6(19)	38(2)	38.5(19)	-1.4(16)	7.2(15)	4.3(15)
C4	28.1(16)	36.3(19)	31.4(17)	1.4(15)	-1.5(13)	-2.6(14)
C7	41(2)	37.8(19)	32.2(18)	-1.8(16)	4.1(15)	0.7(17)
C5	27.4(17)	42(2)	36.7(18)	3.1(17)	2.1(14)	1.8(14)

Table 3 Anisotropic Displacement Parameters (Å²×10³) for 11. The Anisotropic displacement factor exponent takes the form: -2π²[h²a*²U₁₁+2hka*b*U₁₂+…].

Atom

U₁₁

U₂₂

U₃₃

U₂₃

U₁₃

U₁₂

S11

29.1(4)

34.7(4)

33.6(4)

-3.1(4)

-1.4(3)

0.0(4)

26.7(12)

38.6(15)

36.2(13)

-7.5(12)

-2.8(10)

1.5(10)

32.0(14)

52.6(18)

52.3(18)

-15.2(15)

-3.6(13)

7.7(13)

36.7(15)

50.3(17)

35.8(14)

-10.9(13)

-7.0(12)

0.7(12)

N14

34.9(16)

33.7(16)

32.8(15)

-3.9(14)

-3.2(13)

3.0(12)

38.5(16)

54(2)

65(2)

-0.2(18)

-2.6(15)

0.0(14)

N16

43.3(18)

42.1(17)

39.8(17)

-10.9(17)

0.2(14)

0.8(15)

29.6(17)

35.2(18)

33.4(17)

-0.6(15)

-0.4(14)

1.3(14)

N13

36.1(16)

38.4(17)

31.2(15)

-4.1(14)

-4.4(12)

1.5(13)

29.8(17)

38.1(19)

27.1(16)

2.3(15)

-0.9(13)

-4.3(15)

31.5(17)

30.4(18)

27.9(15)

2.9(14)

-1.6(13)

-3.2(13)

C12

34.5(18)

32.5(18)

29.2(17)

1.4(15)

-0.1(14)

-3.6(14)

C10

29.8(17)

31.8(18)

30.6(17)

3.5(14)

0.4(13)

-1.2(13)

28.8(16)

32.2(18)

29.8(16)

3.3(14)

-0.2(13)

-0.6(13)

C15

28.4(16)

28.2(16)

30.2(16)

6.1(14)

-0.4(13)

3.1(13)

35.6(19)

38(2)

38.5(19)

-1.4(16)

7.2(15)

4.3(15)

28.1(16)

36.3(19)

31.4(17)

1.4(15)

-1.5(13)

-2.6(14)

41(2)

37.8(19)

32.2(18)

-1.8(16)

4.1(15)

0.7(17)

27.4(17)

42(2)

36.7(18)

3.1(17)

2.1(14)

1.8(14)

Table 4 Bond Lengths for 11.
Atom	Atom	Length/Å	Atom	Atom	Length/Å
S11	C12	1.740(4)	N13	C12	1.313(5)
S11	C15	1.754(4)	C8	C9	1.393(5)
O1	C2	1.363(5)	C8	C7	1.380(6)
O1	C9	1.368(5)	C3	C15	1.459(5)
O2	C2	1.202(5)	C3	C4	1.347(5)
O3	C8	1.362(5)	C10	C9	1.396(5)
N14	N13	1.378(5)	C10	C4	1.432(5)
N14	C15	1.296(5)	C10	C5	1.402(5)
N16	C12	1.345(5)	C6	C7	1.391(6)
C2	C3	1.472(5)	C6	C5	1.370(6)

Table 4 Bond Lengths for 11.

Atom

Length/Å

Atom

Length/Å

S11

C12

1.740(4)

N13

C12

1.313(5)

S11

C15

1.754(4)

1.393(5)

1.363(5)

1.380(6)

1.368(5)

C15

1.459(5)

1.202(5)

1.347(5)

1.362(5)

C10

1.396(5)

N14

N13

1.378(5)

C10

1.432(5)

N14

C15

1.296(5)

C10

1.402(5)

N16

C12

1.345(5)

1.391(6)

1.472(5)

1.370(6)

Table 5 Bond Angles for 11.
Atom	Atom	Atom	Angle/˚	Atom	Atom	Atom	Angle/˚
C12	S11	C15	86.60(18)	N13	C12	N16	124.2(4)
C2	O1	C9	122.5(3)	C9	C10	C4	117.3(3)
C15	N14	N13	113.3(3)	C9	C10	C5	118.9(4)
O1	C2	C3	117.2(3)	C5	C10	C4	123.8(3)
O2	C2	O1	117.9(3)	O1	C9	C8	117.4(3)
O2	C2	C3	124.8(4)	O1	C9	C10	121.5(3)
C12	N13	N14	112.6(3)	C8	C9	C10	121.1(4)
O3	C8	C9	117.2(3)	N14	C15	S11	113.7(3)
O3	C8	C7	124.2(4)	N14	C15	C3	122.7(3)
C7	C8	C9	118.6(3)	C3	C15	S11	123.6(3)
C15	C3	C2	117.6(3)	C5	C6	C7	120.4(4)
C4	C3	C2	120.0(4)	C3	C4	C10	121.4(3)
C4	C3	C15	122.4(3)	C8	C7	C6	120.9(4)
N16	C12	S11	122.0(3)	C6	C5	C10	120.1(4)
N13	C12	S11	113.8(3)

Table 5 Bond Angles for 11.

Atom

Angle/˚

Atom

Angle/˚

C12

S11

C15

86.60(18)

N13

C12

N16

124.2(4)

122.5(3)

C10

117.3(3)

C15

N14

N13

113.3(3)

C10

118.9(4)

117.2(3)

C10

123.8(3)

117.9(3)

117.4(3)

124.8(4)

C10

121.5(3)

C12

N13

N14

112.6(3)

C10

121.1(4)

117.2(3)

N14

C15

S11

113.7(3)

124.2(4)

N14

C15

122.7(3)

118.6(3)

C15

S11

123.6(3)

C15

117.6(3)

120.4(4)

120.0(4)

C10

121.4(3)

C15

122.4(3)

120.9(4)

N16

C12

S11

122.0(3)

C10

120.1(4)

N13

C12

S11

113.8(3)

Table 6 Torsion Angles for 11.
A	B	C	D	Angle/˚	A	B	C	D	Angle/˚
O1	C2	C3	C15	178.8(3)	C9	C8	C7	C6	0.5(6)
O1	C2	C3	C4	-0.7(5)	C9	C10	C4	C3	-2.6(5)
O2	C2	C3	C15	-1.0(6)	C9	C10	C5	C6	0.1(6)
O2	C2	C3	C4	179.5(4)	C15	S11	C12	N16	179.3(4)
O3	C8	C9	O1	-0.8(5)	C15	S11	C12	N13	0.5(3)
O3	C8	C9	C10	179.4(3)	C15	N14	N13	C12	1.1(5)
O3	C8	C7	C6	-179.6(4)	C15	C3	C4	C10	-176.5(3)
N14	N13	C12	S11	-1.0(4)	C4	C3	C15	S11	-176.9(3)
N14	N13	C12	N16	-179.7(4)	C4	C3	C15	N14	3.0(6)
C2	O1	C9	C8	-177.3(3)	C4	C10	C9	O1	-0.1(5)
C2	O1	C9	C10	2.5(6)	C4	C10	C9	C8	179.7(4)
C2	C3	C15	S11	3.6(5)	C4	C10	C5	C6	-179.1(4)
C2	C3	C15	N14	-176.5(4)	C7	C8	C9	O1	179.1(4)
C2	C3	C4	C10	3.0(6)	C7	C8	C9	C10	-0.7(6)
N13	N14	C15	S11	-0.7(4)	C7	C6	C5	C10	-0.3(6)
N13	N14	C15	C3	179.4(3)	C5	C10	C9	O1	-179.4(3)
C12	S11	C15	N14	0.1(3)	C5	C10	C9	C8	0.4(6)
C12	S11	C15	C3	-180.0(3)	C5	C10	C4	C3	176.6(4)
C9	O1	C2	O2	177.8(4)	C5	C6	C7	C8	0.0(6)
C9	O1	C2	C3	-2.1(5)

Table 6 Torsion Angles for 11.

Angle/˚

C15

178.8(3)

0.5(6)

-0.7(5)

C10

-2.6(5)

C15

-1.0(6)

C10

0.1(6)

179.5(4)

C15

S11

C12

N16

179.3(4)

-0.8(5)

C15

S11

C12

N13

0.5(3)

C10

179.4(3)

C15

N14

N13

C12

1.1(5)

-179.6(4)

C15

C10

-176.5(3)

N14

N13

C12

S11

-1.0(4)

C15

S11

-176.9(3)

N14

N13

C12

N16

-179.7(4)

C15

N14

3.0(6)

-177.3(3)

C10

-0.1(5)

C10

2.5(6)

C10

179.7(4)

C15

S11

3.6(5)

C10

-179.1(4)

C15

N14

-176.5(4)

179.1(4)

C10

3.0(6)

C10

-0.7(6)

N13

N14

C15

S11

-0.7(4)

C10

-0.3(6)

N13

N14

C15

179.4(3)

C10

-179.4(3)

C12

S11

C15

N14

0.1(3)

C10

0.4(6)

C12

S11

C15

-180.0(3)

C10

176.6(4)

177.8(4)

0.0(6)

-2.1(5)

Table 7 Hydrogen Atom Coordinates (Å×10⁴) and Isotropic Displacement Parameters (Å²×10³) for 11.
Atom	x	y	z	U(eq)
H3	6665.96	14904.25	7403.53	62
H4A	9477.74	-2263.32	3687.1	79
H4B	9995.18	206.58	3335.49	79
H16A	4111.17	-532.99	2561.48	50
H16B	6164.65	-453.99	2961.38	50
H6	174.65	15638.28	6675.39	45
H4	1156.71	8497.19	4940.18	39
H7	3317.97	16304.09	7303.33	44
H5	-314.44	12323.82	5732.79	43

Table 7 Hydrogen Atom Coordinates (Å×10⁴) and Isotropic Displacement Parameters (Å²×10³) for 11.

Atom

U(eq)

6665.96

14904.25

7403.53

H4A

9477.74

-2263.32

3687.1

H4B

9995.18

206.58

3335.49

H16A

4111.17

-532.99

2561.48

H16B

6164.65

-453.99

2961.38

174.65

15638.28

6675.39

1156.71

8497.19

4940.18

3317.97

16304.09

7303.33

-314.44

12323.82

5732.79

Table 1 Crystal data and structure refinement for 11.
Identification code	11
Empirical formula	C₁₁H₉N₃O₄S
Formula weight	279.27
Temperature/K	294.37(10)
Crystal system	monoclinic
Space group	Pn
a/Å	6.7057(2)
b/Å	4.7543(2)
c/Å	17.7050(6)
α/°	90
β/°	95.298(3)
γ/°	90
Volume/Å³	562.04(3)
Z	2
ρ_calcg/cm³	1.650
μ/mm^‑1	2.740
F(000)	288.0
Crystal size/mm³	0.3 × 0.2 × 0.02
Radiation	Cu Kα (λ = 1.54184)
2Θ range for data collection/°	10.034 to 152.168
Index ranges	-8 ≤ h ≤ 7, -5 ≤ k ≤ 5, -21 ≤ l ≤ 19
Reflections collected	1983
Independent reflections	1499 [R_int = 0.0259, R_sigma = 0.0518]
Data/restraints/parameters	1499/2/176
Goodness-of-fit on F²	1.049
Final R indexes [I>=2σ (I)]	R₁ = 0.0343, wR₂ = 0.0815
Final R indexes [all data]	R₁ = 0.0358, wR₂ = 0.0833
Largest diff. peak/hole / e Å^-3	0.28/-0.19
Flack parameter	-0.02(3)