201804211

Table 1 Crystal data and structure refinement for 201804211.
Identification code	201804211
Empirical formula	C₁₀H₁₃N₅O₅
Formula weight	283.25
Temperature/K	293(2)
Crystal system	orthorhombic
Space group	P2₁2₁2₁
a/Å	4.7669(2)
b/Å	11.0409(5)
c/Å	21.6334(9)
α/°	90
β/°	90
γ/°	90
Volume/Å³	1138.59(8)
Z	4
ρ_calcg/cm³	1.652
μ/mm^‑1	1.157
F(000)	592.0
Crystal size/mm³	0.15 × 0.11 × 0.1
Radiation	CuKα (λ = 1.54184)
2Θ range for data collection/°	8.174 to 134.138
Index ranges	-3 ≤ h ≤ 5, -13 ≤ k ≤ 13, -25 ≤ l ≤ 25
Reflections collected	4100
Independent reflections	2032 [R_int = 0.0304, R_sigma = 0.0405]
Data/restraints/parameters	2032/0/184
Goodness-of-fit on F²	1.036
Final R indexes [I>=2σ (I)]	R₁ = 0.0366, wR₂ = 0.0880
Final R indexes [all data]	R₁ = 0.0408, wR₂ = 0.0924
Largest diff. peak/hole / e Å^-3	0.14/-0.21
Flack parameter	0.2(2)

Table 2 Fractional Atomic Coordinates (×10⁴) and Equivalent Isotropic Displacement Parameters (Å²×10³) for 201804211. U_eq is defined as 1/3 of of the trace of the orthogonalised U_IJ tensor.
Atom	x	y	z	U(eq)
C1'	4663(6)	2481(2)	3422.2(13)	21.7(6)
C2	832(6)	5821(3)	4035.5(14)	22.7(6)
C2'	7547(6)	2355(3)	3124.7(13)	22.4(6)
C3'	6988(7)	1333(3)	2674.1(13)	25.2(6)
C4	3543(6)	4186(2)	4141.0(13)	20.0(6)
C4'	5133(7)	498(3)	3059.4(14)	25.5(6)
C5	4812(6)	4588(3)	4682.5(13)	22.6(6)
C5'	6688(8)	-481(3)	3405.0(17)	35.6(8)
C6	4144(6)	5762(3)	4902.0(13)	23.5(6)
C7	6793(7)	3686(3)	4838.0(14)	26.0(6)
N1	2061(6)	6311(2)	4554.1(12)	26.0(6)
N3	1519(5)	4751(2)	3805.2(11)	22.0(5)
N4	-1135(6)	6508(2)	3770.3(13)	31.8(6)
N8	6804(6)	2803(2)	4434.6(11)	26.7(6)
N9	4761(5)	3109(2)	4004.7(11)	22.5(5)
O1	3700(5)	1267.1(18)	3504.8(11)	28.8(5)
O2	8443(5)	3436(2)	2836.4(10)	29.5(5)
O3	5381(5)	1733(2)	2162.3(10)	32.2(5)
O4	4822(6)	-1309(2)	3702.3(11)	40.6(6)
O5	5239(5)	6310(2)	5342.1(10)	32.2(5)

Table 2 Fractional Atomic Coordinates (×10⁴) and Equivalent Isotropic Displacement Parameters (Å²×10³) for 201804211. U_eq is defined as 1/3 of of the trace of the orthogonalised U_IJ tensor.

Atom

U(eq)

C1'

4663(6)

2481(2)

3422.2(13)

21.7(6)

832(6)

5821(3)

4035.5(14)

22.7(6)

C2'

7547(6)

2355(3)

3124.7(13)

22.4(6)

C3'

6988(7)

1333(3)

2674.1(13)

25.2(6)

3543(6)

4186(2)

4141.0(13)

20.0(6)

C4'

5133(7)

498(3)

3059.4(14)

25.5(6)

4812(6)

4588(3)

4682.5(13)

22.6(6)

C5'

6688(8)

-481(3)

3405.0(17)

35.6(8)

4144(6)

5762(3)

4902.0(13)

23.5(6)

6793(7)

3686(3)

4838.0(14)

26.0(6)

2061(6)

6311(2)

4554.1(12)

26.0(6)

1519(5)

4751(2)

3805.2(11)

22.0(5)

-1135(6)

6508(2)

3770.3(13)

31.8(6)

6804(6)

2803(2)

4434.6(11)

26.7(6)

4761(5)

3109(2)

4004.7(11)

22.5(5)

3700(5)

1267.1(18)

3504.8(11)

28.8(5)

8443(5)

3436(2)

2836.4(10)

29.5(5)

5381(5)

1733(2)

2162.3(10)

32.2(5)

4822(6)

-1309(2)

3702.3(11)

40.6(6)

5239(5)

6310(2)

5342.1(10)

32.2(5)

Table 3 Anisotropic Displacement Parameters (Å²×10³) for 201804211. The Anisotropic displacement factor exponent takes the form: -2π²[h²a*²U₁₁+2hka*b*U₁₂+…].
Atom	U₁₁	U₂₂	U₃₃	U₂₃	U₁₃	U₁₂
C1'	20.1(14)	18.8(13)	26.2(13)	-1.5(11)	-3.2(12)	-0.2(11)
C2	22.9(14)	19.0(13)	26.1(13)	1.8(11)	1.8(12)	0.8(11)
C2'	20.5(15)	21.9(14)	24.7(13)	0.2(12)	-0.9(12)	0.0(11)
C3'	24.4(15)	24.2(15)	27.0(14)	-4.3(12)	-0.9(12)	5.4(13)
C4	20.3(13)	17.1(12)	22.7(13)	0.8(10)	3.3(12)	-1.3(11)
C4'	26.5(16)	21.5(14)	28.4(14)	-5.9(11)	-3.5(12)	2.3(13)
C5	25.2(15)	20.0(13)	22.8(13)	2.4(11)	0.2(12)	-2.0(12)
C5'	38.1(19)	26.2(16)	42.4(18)	5.4(14)	2.6(16)	7.6(15)
C6	27.5(15)	19.7(14)	23.2(14)	-1.0(11)	2.5(12)	-4.8(12)
C7	28.3(15)	26.2(15)	23.6(13)	2.6(12)	-6.5(12)	0.1(13)
N1	32.9(14)	16.6(11)	28.4(13)	-4.3(10)	1.0(11)	3.8(10)
N3	21.3(12)	19.6(12)	25.1(12)	-0.6(9)	-0.7(10)	-0.1(10)
N4	34.0(15)	26.0(13)	35.4(14)	-5.7(11)	-6.7(12)	9.9(11)
N8	28.8(13)	24.6(12)	26.7(12)	3.3(10)	-3.7(11)	4.5(11)
N9	22.7(12)	19.2(12)	25.7(11)	-0.8(9)	-0.6(10)	4.7(10)
O1	26.0(11)	19.2(10)	41.4(12)	-5.0(9)	7.7(9)	-2.6(9)
O2	29.9(11)	28.8(12)	29.8(11)	2.4(9)	-4.3(9)	-7.3(9)
O3	40.0(13)	30.5(13)	26.0(10)	2.2(9)	-6.9(10)	-5.0(11)
O4	52.3(16)	24.8(11)	44.7(13)	1.1(10)	13.3(13)	6.0(12)
O5	44.1(13)	24.2(10)	28.4(10)	-4.4(9)	-7.2(10)	-4.5(10)

Table 3 Anisotropic Displacement Parameters (Å²×10³) for 201804211. The Anisotropic displacement factor exponent takes the form: -2π²[h²a*²U₁₁+2hka*b*U₁₂+…].

Atom

U₁₁

U₂₂

U₃₃

U₂₃

U₁₃

U₁₂

C1'

20.1(14)

18.8(13)

26.2(13)

-1.5(11)

-3.2(12)

-0.2(11)

22.9(14)

19.0(13)

26.1(13)

1.8(11)

1.8(12)

0.8(11)

C2'

20.5(15)

21.9(14)

24.7(13)

0.2(12)

-0.9(12)

0.0(11)

C3'

24.4(15)

24.2(15)

27.0(14)

-4.3(12)

-0.9(12)

5.4(13)

20.3(13)

17.1(12)

22.7(13)

0.8(10)

3.3(12)

-1.3(11)

C4'

26.5(16)

21.5(14)

28.4(14)

-5.9(11)

-3.5(12)

2.3(13)

25.2(15)

20.0(13)

22.8(13)

2.4(11)

0.2(12)

-2.0(12)

C5'

38.1(19)

26.2(16)

42.4(18)

5.4(14)

2.6(16)

7.6(15)

27.5(15)

19.7(14)

23.2(14)

-1.0(11)

2.5(12)

-4.8(12)

28.3(15)

26.2(15)

23.6(13)

2.6(12)

-6.5(12)

0.1(13)

32.9(14)

16.6(11)

28.4(13)

-4.3(10)

1.0(11)

3.8(10)

21.3(12)

19.6(12)

25.1(12)

-0.6(9)

-0.7(10)

-0.1(10)

34.0(15)

26.0(13)

35.4(14)

-5.7(11)

-6.7(12)

9.9(11)

28.8(13)

24.6(12)

26.7(12)

3.3(10)

-3.7(11)

4.5(11)

22.7(12)

19.2(12)

25.7(11)

-0.8(9)

-0.6(10)

4.7(10)

26.0(11)

19.2(10)

41.4(12)

-5.0(9)

7.7(9)

-2.6(9)

29.9(11)

28.8(12)

29.8(11)

2.4(9)

-4.3(9)

-7.3(9)

40.0(13)

30.5(13)

26.0(10)

2.2(9)

-6.9(10)

-5.0(11)

52.3(16)

24.8(11)

44.7(13)

1.1(10)

13.3(13)

6.0(12)

44.1(13)

24.2(10)

28.4(10)

-4.4(9)

-7.2(10)

-4.5(10)

Table 4 Bond Lengths for 201804211.
Atom	Atom	Length/Å	Atom	Atom	Length/Å
C1'	C2'	1.524(4)	C4	N3	1.360(4)
C1'	N9	1.439(4)	C4	N9	1.356(4)
C1'	O1	1.428(3)	C4'	C5'	1.510(4)
C2	N1	1.377(4)	C4'	O1	1.454(4)
C2	N3	1.323(4)	C5	C6	1.416(4)
C2	N4	1.335(4)	C5	C7	1.413(4)
C2'	C3'	1.515(4)	C5'	O4	1.428(4)
C2'	O2	1.413(3)	C6	N1	1.386(4)
C3'	C4'	1.525(4)	C6	O5	1.243(4)
C3'	O3	1.417(4)	C7	N8	1.308(4)
C4	C5	1.391(4)	N8	N9	1.388(3)

Table 4 Bond Lengths for 201804211.

Atom

Length/Å

Atom

Length/Å

C1'

C2'

1.524(4)

1.360(4)

C1'

1.439(4)

1.356(4)

C1'

1.428(3)

C4'

C5'

1.510(4)

1.377(4)

C4'

1.454(4)

1.323(4)

1.416(4)

1.335(4)

1.413(4)

C2'

C3'

1.515(4)

C5'

1.428(4)

C2'

1.413(3)

1.386(4)

C3'

C4'

1.525(4)

1.243(4)

C3'

1.417(4)

1.308(4)

1.391(4)

1.388(3)

Table 5 Bond Angles for 201804211.
Atom	Atom	Atom	Angle/˚	Atom	Atom	Atom	Angle/˚
N9	C1'	C2'	112.6(2)	O1	C4'	C5'	108.7(3)
O1	C1'	C2'	104.9(2)	C4	C5	C6	118.4(3)
O1	C1'	N9	110.7(2)	C4	C5	C7	105.4(3)
N3	C2	N1	123.6(3)	C7	C5	C6	135.7(3)
N3	C2	N4	121.3(3)	O4	C5'	C4'	112.1(3)
N4	C2	N1	115.2(3)	N1	C6	C5	112.3(3)
C3'	C2'	C1'	100.4(2)	O5	C6	C5	127.4(3)
O2	C2'	C1'	112.5(2)	O5	C6	N1	120.2(3)
O2	C2'	C3'	113.5(2)	N8	C7	C5	111.7(3)
C2'	C3'	C4'	101.6(2)	C2	N1	C6	125.1(2)
O3	C3'	C2'	111.4(2)	C2	N3	C4	112.6(3)
O3	C3'	C4'	107.6(3)	C7	N8	N9	105.2(2)
N3	C4	C5	127.8(3)	C4	N9	C1'	126.8(2)
N9	C4	C5	106.1(3)	C4	N9	N8	111.6(2)
N9	C4	N3	126.2(3)	N8	N9	C1'	119.5(2)
C5'	C4'	C3'	114.8(3)	C1'	O1	C4'	108.3(2)
O1	C4'	C3'	106.4(2)

Table 5 Bond Angles for 201804211.

Atom

Angle/˚

Atom

Angle/˚

C1'

C2'

112.6(2)

C4'

C5'

108.7(3)

C1'

C2'

104.9(2)

118.4(3)

C1'

110.7(2)

105.4(3)

123.6(3)

135.7(3)

121.3(3)

C5'

C4'

112.1(3)

115.2(3)

112.3(3)

C3'

C2'

C1'

100.4(2)

127.4(3)

C2'

C1'

112.5(2)

120.2(3)

C2'

C3'

113.5(2)

111.7(3)

C2'

C3'

C4'

101.6(2)

125.1(2)

C3'

C2'

111.4(2)

112.6(3)

C3'

C4'

107.6(3)

105.2(2)

127.8(3)

C1'

126.8(2)

106.1(3)

111.6(2)

126.2(3)

C1'

119.5(2)

C5'

C4'

C3'

114.8(3)

C1'

C4'

108.3(2)

C4'

C3'

106.4(2)

Table 6 Hydrogen Bonds for 201804211.
D	H	A	d(D-H)/Å	d(H-A)/Å	d(D-A)/Å	D-H-A/°
N1	H1	O5¹	0.86	1.94	2.775(3)	161.9
N4	H4A	O3²	0.86	2.15	2.869(3)	140.9
N4	H4B	O4³	0.86	2.43	3.090(4)	133.5
N4	H4B	O5¹	0.86	2.44	3.150(3)	140.7
O2	H2	N3⁴	0.82	2.13	2.941(3)	172.9
O3	H3	O4⁵	0.82	2.21	2.860(3)	135.7
O4	H4	O5⁶	0.82	2.34	3.008(3)	139.3

Table 6 Hydrogen Bonds for 201804211.

d(D-H)/Å

d(H-A)/Å

d(D-A)/Å

D-H-A/°

O5¹

0.86

1.94

2.775(3)

161.9

H4A

O3²

0.86

2.15

2.869(3)

140.9

H4B

O4³

0.86

2.43

3.090(4)

133.5

H4B

O5¹

0.86

2.44

3.150(3)

140.7

N3⁴

0.82

2.13

2.941(3)

172.9

O4⁵

0.82

2.21

2.860(3)

135.7

O5⁶

0.82

2.34

3.008(3)

139.3

¹-1/2+X,3/2-Y,1-Z; ²-X,1/2+Y,1/2-Z; ³-1+X,1+Y,+Z; ⁴1+X,+Y,+Z; ⁵1-X,1/2+Y,1/2-Z; ⁶-1/2+X,1/2-Y,1-Z

Table 7 Torsion Angles for 201804211.
A	B	C	D	Angle/˚	A	B	C	D	Angle/˚
C1'	C2'	C3'	C4'	-40.3(3)	N3	C2	N1	C6	-0.2(5)
C1'	C2'	C3'	O3	74.0(3)	N3	C4	C5	C6	-5.5(5)
C2'	C1'	N9	C4	116.3(3)	N3	C4	C5	C7	-179.0(3)
C2'	C1'	N9	N8	-45.7(3)	N3	C4	N9	C1'	15.3(5)
C2'	C1'	O1	C4'	-24.2(3)	N3	C4	N9	N8	178.5(3)
C2'	C3'	C4'	C5'	-92.9(3)	N4	C2	N1	C6	-179.9(3)
C2'	C3'	C4'	O1	27.3(3)	N4	C2	N3	C4	-179.6(3)
C3'	C4'	C5'	O4	-173.7(2)	N9	C1'	C2'	C3'	161.0(2)
C3'	C4'	O1	C1'	-2.1(3)	N9	C1'	C2'	O2	-78.0(3)
C4	C5	C6	N1	5.2(4)	N9	C1'	O1	C4'	-145.9(2)
C4	C5	C6	O5	-173.2(3)	N9	C4	C5	C6	173.7(3)
C4	C5	C7	N8	0.5(4)	N9	C4	C5	C7	0.2(3)
C5	C4	N3	C2	2.2(4)	N9	C4	N3	C2	-176.9(3)
C5	C4	N9	C1'	-164.0(3)	O1	C1'	C2'	C3'	40.6(3)
C5	C4	N9	N8	-0.8(3)	O1	C1'	C2'	O2	161.5(2)
C5	C6	N1	C2	-2.8(4)	O1	C1'	N9	C4	-126.6(3)
C5	C7	N8	N9	-0.9(3)	O1	C1'	N9	N8	71.3(3)
C5'	C4'	O1	C1'	122.0(3)	O1	C4'	C5'	O4	67.4(3)
C6	C5	C7	N8	-171.4(3)	O2	C2'	C3'	C4'	-160.5(2)
C7	C5	C6	N1	176.3(3)	O2	C2'	C3'	O3	-46.2(3)
C7	C5	C6	O5	-2.1(6)	O3	C3'	C4'	C5'	150.0(3)
C7	N8	N9	C1'	165.6(3)	O3	C3'	C4'	O1	-89.8(3)
C7	N8	N9	C4	1.0(3)	O5	C6	N1	C2	175.7(3)
N1	C2	N3	C4	0.7(4)

Table 7 Torsion Angles for 201804211.

Angle/˚

C1'

C2'

C3'

C4'

-40.3(3)

-0.2(5)

C1'

C2'

C3'

74.0(3)

-5.5(5)

C2'

C1'

116.3(3)

-179.0(3)

C2'

C1'

-45.7(3)

C1'

15.3(5)

C2'

C1'

C4'

-24.2(3)

178.5(3)

C2'

C3'

C4'

C5'

-92.9(3)

-179.9(3)

C2'

C3'

C4'

27.3(3)

-179.6(3)

C3'

C4'

C5'

-173.7(2)

C1'

C2'

C3'

161.0(2)

C3'

C4'

C1'

-2.1(3)

C1'

C2'

-78.0(3)

5.2(4)

C1'

C4'

-145.9(2)

-173.2(3)

173.7(3)

0.5(4)

0.2(3)

2.2(4)

-176.9(3)

C1'

-164.0(3)

C1'

C2'

C3'

40.6(3)

-0.8(3)

C1'

C2'

161.5(2)

-2.8(4)

C1'

-126.6(3)

-0.9(3)

C1'

71.3(3)

C5'

C4'

C1'

122.0(3)

C4'

C5'

67.4(3)

-171.4(3)

C2'

C3'

C4'

-160.5(2)

176.3(3)

C2'

C3'

-46.2(3)

-2.1(6)

C3'

C4'

C5'

150.0(3)

C1'

165.6(3)

C3'

C4'

-89.8(3)

1.0(3)

175.7(3)

0.7(4)

Table 8 Hydrogen Atom Coordinates (Å×10⁴) and Isotropic Displacement Parameters (Å²×10³) for 201804211.
Atom	x	y	z	U(eq)
H1'	3401	2909	3139	26
H2'	8926	2099	3434	27
H3'	8724	931	2544	30
H4'	3735	121	2789	31
H5'A	7871	-923	3118	43
H5'B	7892	-111	3713	43
H7	7946	3716	5184	31
H1	1492	7014	4671	31
H4A	-1981	6257	3443	38
H4B	-1554	7201	3926	38
H2	9277	3859	3088	44
H3	6248	2261	1976	48
H4	3933	-952	3971	61

Table 8 Hydrogen Atom Coordinates (Å×10⁴) and Isotropic Displacement Parameters (Å²×10³) for 201804211.

Atom

U(eq)

H1'

3401

2909

3139

H2'

8926

2099

3434

H3'

8724

931

2544

H4'

3735

121

2789

H5'A

7871

-923

3118

H5'B

7892

-111

3713

7946

3716

5184

1492

7014

4671

H4A

-1981

6257

3443

H4B

-1554

7201

3926

9277

3859

3088

6248

2261

1976

3933

-952

3971

Experimental

Single crystals of C₁₀H₁₃N₅O₅ [201804211] were []. A suitable crystal was selected and [] on a Xcalibur, Eos, Gemini diffractometer. The crystal was kept at 293(2) K during data collection. Using Olex2 [1], the structure was solved with the ShelXS [2] structure solution program using Direct Methods and refined with the ShelXL [3] refinement package using Least Squares minimisation.

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341.
Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.

Crystal structure determination of [201804211]

Crystal Data for C₁₀H₁₃N₅O₅ (M =283.25 g/mol): orthorhombic, space group P2₁2₁2₁ (no. 19), a = 4.7669(2) Å, b = 11.0409(5) Å, c = 21.6334(9) Å, V = 1138.59(8) Å³, Z = 4, T = 293(2) K, μ(CuKα) = 1.157 mm^-1, Dcalc = 1.652 g/cm³, 4100 reflections measured (8.174° ≤ 2Θ ≤ 134.138°), 2032 unique (R_int = 0.0304, R_sigma = 0.0405) which were used in all calculations. The final R₁ was 0.0366 (I > 2σ(I)) and wR₂ was 0.0924 (all data).

Refinement model description

Number of restraints - 0, number of constraints - unknown.

Details:

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4')
2.b Secondary CH2 refined with riding coordinates:
 C5'(H5'A,H5'B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), N1(H1)
2.d X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O4(H4)

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