36

Table 1 Crystal data and structure refinement for 36.
Identification code	36
Empirical formula	C₁₃H₁₁ClN₄O₂
Formula weight	290.71
Temperature/K	293(2)
Crystal system	monoclinic
Space group	P2₁/c
a/Å	11.7767(7)
b/Å	14.4529(7)
c/Å	7.9073(4)
α/°	90
β/°	91.381(5)
γ/°	90
Volume/Å³	1345.49(12)
Z	4
ρ_calcg/cm³	1.435
μ/mm^‑1	0.291
F(000)	600.0
Crystal size/mm³	0.14 × 0.13 × 0.12
Radiation	Mo Kα (λ = 0.71073)
2Θ range for data collection/°	6.756 to 49.996
Index ranges	-8 ≤ h ≤ 14, -16 ≤ k ≤ 16, -8 ≤ l ≤ 9
Reflections collected	4286
Independent reflections	2343 [R_int = 0.0161, R_sigma = 0.0302]
Data/restraints/parameters	2343/0/182
Goodness-of-fit on F²	1.047
Final R indexes [I>=2σ (I)]	R₁ = 0.0548, wR₂ = 0.1338
Final R indexes [all data]	R₁ = 0.0790, wR₂ = 0.1491
Largest diff. peak/hole / e Å^-3	0.21/-0.41

Table 2 Fractional Atomic Coordinates (×10⁴) and Equivalent Isotropic Displacement Parameters (Å²×10³) for 36. U_eq is defined as 1/3 of of the trace of the orthogonalised U_IJ tensor.
Atom	x	y	z	U(eq)
Cl11	4103.2(9)	9336.3(6)	7985.1(11)	102.1(4)
O19	10977(2)	5282(2)	1630(4)	128.2(10)
O20	9892(2)	4189(2)	2457(4)	117.1(9)
N1	4418.5(18)	6616.3(16)	7584(3)	65.2(6)
N7	5479.5(17)	7847.2(13)	6578(3)	56.8(6)
N8	6246.3(17)	7260.4(13)	5911(2)	50.5(5)
N18	10137(2)	5001(2)	2323(4)	86.1(8)
C6	3497(3)	6328(3)	8375(4)	85.1(10)
C5	2698(3)	6905(3)	9029(4)	96.9(12)
C4	2865(3)	7841(3)	8911(4)	92.5(11)
C3	3818(2)	8164(2)	8129(3)	70.4(8)
C2	4563(2)	7524.8(19)	7439(3)	55.1(6)
C9	7042.2(19)	7614.1(15)	5031(3)	47.7(6)
C12	7857.7(19)	6942.6(15)	4359(3)	47.3(6)
C17	8840(2)	7219.9(18)	3559(3)	60.7(7)
C16	9589(2)	6595(2)	2912(4)	69.0(8)
C15	9358(2)	5676.3(19)	3059(3)	62.3(7)
C14	8403(2)	5362.8(17)	3855(3)	64.4(7)
C13	7656(2)	5993.6(16)	4503(3)	57.8(7)
C10	7157(2)	8631.5(16)	4663(4)	62.3(7)

Table 2 Fractional Atomic Coordinates (×10⁴) and Equivalent Isotropic Displacement Parameters (Å²×10³) for 36. U_eq is defined as 1/3 of of the trace of the orthogonalised U_IJ tensor.

Atom

U(eq)

Cl11

4103.2(9)

9336.3(6)

7985.1(11)

102.1(4)

O19

10977(2)

5282(2)

1630(4)

128.2(10)

O20

9892(2)

4189(2)

2457(4)

117.1(9)

4418.5(18)

6616.3(16)

7584(3)

65.2(6)

5479.5(17)

7847.2(13)

6578(3)

56.8(6)

6246.3(17)

7260.4(13)

5911(2)

50.5(5)

N18

10137(2)

5001(2)

2323(4)

86.1(8)

3497(3)

6328(3)

8375(4)

85.1(10)

2698(3)

6905(3)

9029(4)

96.9(12)

2865(3)

7841(3)

8911(4)

92.5(11)

3818(2)

8164(2)

8129(3)

70.4(8)

4563(2)

7524.8(19)

7439(3)

55.1(6)

7042.2(19)

7614.1(15)

5031(3)

47.7(6)

C12

7857.7(19)

6942.6(15)

4359(3)

47.3(6)

C17

8840(2)

7219.9(18)

3559(3)

60.7(7)

C16

9589(2)

6595(2)

2912(4)

69.0(8)

C15

9358(2)

5676.3(19)

3059(3)

62.3(7)

C14

8403(2)

5362.8(17)

3855(3)

64.4(7)

C13

7656(2)

5993.6(16)

4503(3)

57.8(7)

C10

7157(2)

8631.5(16)

4663(4)

62.3(7)

Table 3 Anisotropic Displacement Parameters (Å²×10³) for 36. The Anisotropic displacement factor exponent takes the form: -2π²[h²a*²U₁₁+2hka*b*U₁₂+…].
Atom	U₁₁	U₂₂	U₃₃	U₂₃	U₁₃	U₁₂
Cl11	125.1(8)	83.6(6)	98.3(7)	-13.5(5)	15.3(6)	40.3(5)
O19	90.7(18)	146(2)	150(3)	-4.1(19)	44.1(18)	38.3(17)
O20	113(2)	90.5(18)	147(2)	-33.2(17)	-3.4(17)	39.5(16)
N1	62.8(13)	70.3(15)	62.5(14)	0.1(12)	0.6(11)	-7.5(11)
N7	63.9(13)	50.4(11)	56.3(13)	-0.2(10)	6.7(11)	7.4(10)
N8	55.0(11)	49.0(11)	47.4(12)	-2.4(9)	-1.8(9)	5.0(9)
N18	77.8(18)	95(2)	85.1(19)	-15.5(17)	-6.6(15)	31.8(16)
C6	79(2)	106(3)	70(2)	1.5(18)	-3.5(17)	-28.3(19)
C5	60.8(19)	159(4)	71(2)	-11(2)	7.5(16)	-20(2)
C4	64(2)	143(3)	70(2)	-23(2)	0.6(17)	18(2)
C3	66.4(17)	91(2)	54.0(16)	-9.2(15)	-1.5(14)	17.9(15)
C2	55.0(14)	66.6(16)	43.3(14)	-2.4(12)	-6.8(12)	5.8(13)
C9	54.4(13)	43.8(12)	44.8(14)	0.2(11)	-3.3(11)	-4.0(11)
C12	51.7(13)	44.1(12)	45.8(13)	2.5(11)	-3.5(11)	0.1(10)
C17	58.0(15)	54.5(15)	69.8(18)	5.5(13)	5.4(13)	-5.5(12)
C16	55.4(15)	80(2)	72.1(19)	2.8(16)	7.9(14)	0.8(14)
C15	54.6(15)	73.4(18)	58.5(16)	-6.1(14)	-5.2(13)	17.0(13)
C14	77.4(18)	46.6(14)	69.0(17)	0.2(13)	-1.5(15)	10.0(13)
C13	61.7(15)	49.7(14)	62.1(16)	3.4(12)	7.9(13)	-2.2(12)
C10	72.1(17)	44.5(14)	70.4(18)	1.9(13)	4.0(14)	-0.7(12)

Table 3 Anisotropic Displacement Parameters (Å²×10³) for 36. The Anisotropic displacement factor exponent takes the form: -2π²[h²a*²U₁₁+2hka*b*U₁₂+…].

Atom

U₁₁

U₂₂

U₃₃

U₂₃

U₁₃

U₁₂

Cl11

125.1(8)

83.6(6)

98.3(7)

-13.5(5)

15.3(6)

40.3(5)

O19

90.7(18)

146(2)

150(3)

-4.1(19)

44.1(18)

38.3(17)

O20

113(2)

90.5(18)

147(2)

-33.2(17)

-3.4(17)

39.5(16)

62.8(13)

70.3(15)

62.5(14)

0.1(12)

0.6(11)

-7.5(11)

63.9(13)

50.4(11)

56.3(13)

-0.2(10)

6.7(11)

7.4(10)

55.0(11)

49.0(11)

47.4(12)

-2.4(9)

-1.8(9)

5.0(9)

N18

77.8(18)

95(2)

85.1(19)

-15.5(17)

-6.6(15)

31.8(16)

79(2)

106(3)

70(2)

1.5(18)

-3.5(17)

-28.3(19)

60.8(19)

159(4)

71(2)

-11(2)

7.5(16)

-20(2)

64(2)

143(3)

70(2)

-23(2)

0.6(17)

18(2)

66.4(17)

91(2)

54.0(16)

-9.2(15)

-1.5(14)

17.9(15)

55.0(14)

66.6(16)

43.3(14)

-2.4(12)

-6.8(12)

5.8(13)

54.4(13)

43.8(12)

44.8(14)

0.2(11)

-3.3(11)

-4.0(11)

C12

51.7(13)

44.1(12)

45.8(13)

2.5(11)

-3.5(11)

0.1(10)

C17

58.0(15)

54.5(15)

69.8(18)

5.5(13)

5.4(13)

-5.5(12)

C16

55.4(15)

80(2)

72.1(19)

2.8(16)

7.9(14)

0.8(14)

C15

54.6(15)

73.4(18)

58.5(16)

-6.1(14)

-5.2(13)

17.0(13)

C14

77.4(18)

46.6(14)

69.0(17)

0.2(13)

-1.5(15)

10.0(13)

C13

61.7(15)

49.7(14)

62.1(16)

3.4(12)

7.9(13)

-2.2(12)

C10

72.1(17)

44.5(14)

70.4(18)

1.9(13)

4.0(14)

-0.7(12)

Table 4 Bond Lengths for 36.
Atom	Atom	Length/Å	Atom	Atom	Length/Å
Cl11	C3	1.732(3)	C4	C3	1.375(4)
O19	N18	1.213(4)	C3	C2	1.394(4)
O20	N18	1.213(4)	C9	C12	1.474(3)
N1	C6	1.333(4)	C9	C10	1.505(3)
N1	C2	1.329(3)	C12	C17	1.391(3)
N7	N8	1.355(3)	C12	C13	1.397(3)
N7	C2	1.371(3)	C17	C16	1.369(4)
N8	C9	1.287(3)	C16	C15	1.361(4)
N18	C15	1.469(4)	C15	C14	1.379(4)
C6	C5	1.368(5)	C14	C13	1.375(3)
C5	C4	1.371(5)

Table 4 Bond Lengths for 36.

Atom

Length/Å

Atom

Length/Å

Cl11

1.732(3)

1.375(4)

O19

N18

1.213(4)

1.394(4)

O20

N18

1.213(4)

C12

1.474(3)

1.333(4)

C10

1.505(3)

1.329(3)

C12

C17

1.391(3)

1.355(3)

C12

C13

1.397(3)

1.371(3)

C17

C16

1.369(4)

1.287(3)

C16

C15

1.361(4)

N18

C15

1.469(4)

C15

C14

1.379(4)

1.368(5)

C14

C13

1.375(3)

1.371(5)

Table 5 Bond Angles for 36.
Atom	Atom	Atom	Angle/˚	Atom	Atom	Atom	Angle/˚
C2	N1	C6	117.2(3)	N7	C2	C3	118.7(2)
N8	N7	C2	121.4(2)	N8	C9	C12	115.0(2)
C9	N8	N7	117.57(19)	N8	C9	C10	124.2(2)
O19	N18	O20	124.1(3)	C12	C9	C10	120.8(2)
O19	N18	C15	118.7(3)	C17	C12	C9	122.1(2)
O20	N18	C15	117.2(3)	C17	C12	C13	117.7(2)
N1	C6	C5	124.2(3)	C13	C12	C9	120.2(2)
C6	C5	C4	118.3(3)	C16	C17	C12	122.0(2)
C5	C4	C3	119.0(3)	C15	C16	C17	118.7(2)
C4	C3	Cl11	121.5(3)	C16	C15	N18	119.2(3)
C4	C3	C2	118.7(3)	C16	C15	C14	121.7(2)
C2	C3	Cl11	119.8(2)	C14	C15	N18	119.1(3)
N1	C2	N7	118.9(2)	C13	C14	C15	119.3(2)
N1	C2	C3	122.5(2)	C14	C13	C12	120.6(2)

Table 5 Bond Angles for 36.

Atom

Angle/˚

Atom

Angle/˚

117.2(3)

118.7(2)

121.4(2)

C12

115.0(2)

117.57(19)

C10

124.2(2)

O19

N18

O20

124.1(3)

C12

C10

120.8(2)

O19

N18

C15

118.7(3)

C17

C12

122.1(2)

O20

N18

C15

117.2(3)

C17

C12

C13

117.7(2)

124.2(3)

C13

C12

120.2(2)

118.3(3)

C16

C17

C12

122.0(2)

119.0(3)

C15

C16

C17

118.7(2)

Cl11

121.5(3)

C16

C15

N18

119.2(3)

118.7(3)

C16

C15

C14

121.7(2)

Cl11

119.8(2)

C14

C15

N18

119.1(3)

118.9(2)

C13

C14

C15

119.3(2)

122.5(2)

C14

C13

C12

120.6(2)

Table 6 Torsion Angles for 36.
A	B	C	D	Angle/˚	A	B	C	D	Angle/˚
Cl11	C3	C2	N1	176.6(2)	C5	C4	C3	Cl11	-178.2(3)
Cl11	C3	C2	N7	-3.5(3)	C5	C4	C3	C2	1.9(5)
O19	N18	C15	C16	1.4(4)	C4	C3	C2	N1	-3.5(4)
O19	N18	C15	C14	-179.7(3)	C4	C3	C2	N7	176.5(3)
O20	N18	C15	C16	-178.9(3)	C2	N1	C6	C5	0.4(4)
O20	N18	C15	C14	0.0(4)	C2	N7	N8	C9	175.7(2)
N1	C6	C5	C4	-1.9(5)	C9	C12	C17	C16	-179.0(2)
N7	N8	C9	C12	179.23(19)	C9	C12	C13	C14	178.9(2)
N7	N8	C9	C10	-1.6(3)	C12	C17	C16	C15	0.1(4)
N8	N7	C2	N1	-1.4(3)	C17	C12	C13	C14	-0.7(4)
N8	N7	C2	C3	178.6(2)	C17	C16	C15	N18	178.1(3)
N8	C9	C12	C17	-172.1(2)	C17	C16	C15	C14	-0.8(4)
N8	C9	C12	C13	8.3(3)	C16	C15	C14	C13	0.7(4)
N18	C15	C14	C13	-178.2(2)	C15	C14	C13	C12	0.0(4)
C6	N1	C2	N7	-177.6(2)	C13	C12	C17	C16	0.6(4)
C6	N1	C2	C3	2.4(4)	C10	C9	C12	C17	8.7(3)
C6	C5	C4	C3	0.7(5)	C10	C9	C12	C13	-170.9(2)

Table 6 Torsion Angles for 36.

Angle/˚

Cl11

176.6(2)

Cl11

-178.2(3)

Cl11

-3.5(3)

1.9(5)

O19

N18

C15

C16

1.4(4)

-3.5(4)

O19

N18

C15

C14

-179.7(3)

176.5(3)

O20

N18

C15

C16

-178.9(3)

0.4(4)

O20

N18

C15

C14

0.0(4)

175.7(2)

-1.9(5)

C12

C17

C16

-179.0(2)

C12

179.23(19)

C12

C13

C14

178.9(2)

C10

-1.6(3)

C12

C17

C16

C15

0.1(4)

-1.4(3)

C17

C12

C13

C14

-0.7(4)

178.6(2)

C17

C16

C15

N18

178.1(3)

C12

C17

-172.1(2)

C17

C16

C15

C14

-0.8(4)

C12

C13

8.3(3)

C16

C15

C14

C13

0.7(4)

N18

C15

C14

C13

-178.2(2)

C15

C14

C13

C12

0.0(4)

-177.6(2)

C13

C12

C17

C16

0.6(4)

2.4(4)

C10

C12

C17

8.7(3)

0.7(5)

C10

C12

C13

-170.9(2)

Table 7 Hydrogen Atom Coordinates (Å×10⁴) and Isotropic Displacement Parameters (Å²×10³) for 36.
Atom	x	y	z	U(eq)
H7	5569	8434	6460	68
H6	3390	5694	8491	102
H5	2057	6668	9540	116
H4	2342	8252	9353	111
H17	8993	7849	3461	73
H16	10241	6795	2383	83
H14	8266	4732	3952	77
H13	7010	5787	5042	69
H10A	6465	8856	4144	93
H10B	7774	8727	3911	93
H10C	7305	8960	5701	93

Table 7 Hydrogen Atom Coordinates (Å×10⁴) and Isotropic Displacement Parameters (Å²×10³) for 36.

Atom

U(eq)

5569

8434

6460

3390

5694

8491

102

2057

6668

9540

116

2342

8252

9353

111

H17

8993

7849

3461

H16

10241

6795

2383

H14

8266

4732

3952

H13

7010

5787

5042

H10A

6465

8856

4144

H10B

7774

8727

3911

H10C

7305

8960

5701

Experimental

Single crystals of C₁₃H₁₁ClN₄O₂ [36] were []. A suitable crystal was selected and [] on a SuperNova, Single source at offset, Eos diffractometer. The crystal was kept at 293(2) K during data collection. Using Olex2 [1], the structure was solved with the SHELXT [2] structure solution program using Intrinsic Phasing and refined with the XL [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. (2015). Acta Cryst. A71, 3-8.
Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Crystal structure determination of [36]

Crystal Data for C₁₃H₁₁ClN₄O₂ (M =290.71 g/mol): monoclinic, space group P2₁/c (no. 14), a = 11.7767(7) Å, b = 14.4529(7) Å, c = 7.9073(4) Å, β = 91.381(5)°, V = 1345.49(12) Å³, Z = 4, T = 293(2) K, μ(Mo Kα) = 0.291 mm^-1, Dcalc = 1.435 g/cm³, 4286 reflections measured (6.756° ≤ 2Θ ≤ 49.996°), 2343 unique (R_int = 0.0161, R_sigma = 0.0302) which were used in all calculations. The final R₁ was 0.0548 (I > 2σ(I)) and wR₂ was 0.1491 (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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N7(H7), C6(H6), C5(H5), C4(H4), C17(H17), C16(H16), C14(H14), C13(H13)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)

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