Tables from CIF for the Compound 1

1

Supplementary materials

(Tables from CIF for the compound 1)

Table 1. Crystal data and structure refinement for the compound 1.

Identification code Compound 1

Empirical formula C18H22N6O4

Formula weight 386.42

Temperature 110(2) K

Wavelength 0.71073 Å

Crystal system Triclinic

Space group P-1

Unit cell dimensionsa = 8.7959(10) Å= 96.901(2)°.

b = 10.5312(12) Å= 98.135(2)°.

c = 10.6802(12) Å = 107.248(2)°.

Volume921.47(18) Å3

Z2

Density (calculated)1.393 Mg/m3

Absorption coefficient0.102 mm-1

F(000)408

Crystal size0.50 x 0.20 x 0.20 mm3

Theta range for data collection1.96 to 30.08°.

Index ranges-12<=h<=11, -14<=k<=14, -14<=l<=7

Reflections collected7201

Independent reflections5055 [R(int) = 0.0143]

Completeness to theta = 30.08°93.4 %

Absorption correctionSemi-empirical from equivalents

Max. and min. transmission0.9800 and 0.9509

Refinement methodFull-matrix least-squares on F2

Data / restraints / parameters5055 / 0 / 258

Goodness-of-fit on F21.001

Final R indices [I>2sigma(I)]R1 = 0.0466, wR2 = 0.1262

R indices (all data)R1 = 0.0589, wR2 = 0.1337

Largest diff. peak and hole0.406 and -0.252 e.Å-3

Table 2. Atomic coordinates ( x 104) and equivalent isotropic displacement parameters (Å2x 103)

for the compound 1. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.

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xyzU(eq)

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O(1A) 4550(1) 10751(1) 7956(1) 26(1)

N(1A) 1978(1) 10027(1) 4332(1) 22(1)

N(2A) 3562(1) 9417(1) 5977(1) 20(1)

N(3A) 4219(1) 8427(1) 6241(1) 23(1)

C(1A) 2090(1) 11167(1) 5137(1) 22(1)

C(2A) 2925(1) 11439(1) 6370(1) 22(1)

C(3A) 3749(1) 10570(1) 6870(1) 21(1)

C(4A) 3745(1) 7538(1) 5148(1) 24(1)

C(5A) 2794(1) 7922(1) 4174(1) 24(1)

C(6A) 2705(1) 9136(1) 4738(1) 20(1)

C(7A) 1277(2) 12085(1) 4572(1) 27(1)

C(8A) 4210(2) 6283(1) 5052(1) 29(1)

O(1B) -124(1) 926(1) -1943(1) 26(1)

N(1B) 3292(1) 272(1) 647(1) 21(1)

N(2B) 2029(1) 1697(1) -289(1) 20(1)

N(3B) 2069(1) 3013(1) -175(1) 22(1)

C(1B) 2227(1) -803(1) -185(1) 21(1)

C(2B) 1069(1) -631(1) -1090(1) 23(1)

C(3B) 892(1) 655(1) -1194(1) 21(1)

C(4B) 3287(1) 3666(1) 807(1) 23(1)

C(5B) 4033(1) 2795(1) 1342(1) 22(1)

C(6B) 3193(1) 1536(1) 623(1) 20(1)

C(7B) 2375(2) -2158(1) -51(1) 28(1)

C(8B) 3708(2) 5157(1) 1196(1) 30(1)

O(1S) 328(1) 4196(1) -1630(1) 30(1)

O(2S) 2353(1) 4635(1) -2720(1) 38(1)

C(1S) 1107(2) 4777(1) -2485(1) 25(1)

C(2S) 254(2) 5624(1) -3153(1) 34(1)

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Table 3. Bond lengths [Å] and angles [°] for the compound 1.

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O(1A)-C(3A) 1.2302(14)

N(1A)-C(1A) 1.3585(15)

N(1A)-C(6A) 1.3610(14)

N(1A)-H(1A) 0.8800

N(2A)-N(3A) 1.3718(13)

N(2A)-C(6A) 1.3777(14)

N(2A)-C(3A) 1.4031(15)

N(3A)-C(4A) 1.3349(16)

C(1A)-C(2A) 1.3667(16)

C(1A)-C(7A) 1.4961(16)

C(2A)-C(3A) 1.4312(16)

C(2A)-H(2A) 0.9500

C(4A)-C(5A) 1.4147(17)

C(4A)-C(8A) 1.4913(17)

C(5A)-C(6A) 1.3754(16)

C(5A)-H(5A) 0.9500

C(7A)-H(7A) 0.9800

C(7A)-H(7B) 0.9800

C(7A)-H(7C) 0.9800

C(8A)-H(8A) 0.9800

C(8A)-H(8B) 0.9800

C(8A)-H(8C) 0.9800

O(1B)-C(3B) 1.2344(14)

N(1B)-C(1B) 1.3573(14)

N(1B)-C(6B) 1.3625(14)

N(1B)-H(1B) 0.8800

N(2B)-N(3B) 1.3662(13)

N(2B)-C(6B) 1.3727(14)

N(2B)-C(3B) 1.3999(14)

N(3B)-C(4B) 1.3388(15)

C(1B)-C(2B) 1.3707(16)

C(1B)-C(7B) 1.4929(16)

C(2B)-C(3B) 1.4239(16)

C(2B)-H(2B) 0.9500

C(4B)-C(5B) 1.4057(16)

C(4B)-C(8B) 1.4938(17)

C(5B)-C(6B) 1.3803(15)

C(5B)-H(5B) 0.9500

C(7B)-H(7D) 0.9800

C(7B)-H(7E) 0.9800

C(7B)-H(7F) 0.9800

C(8B)-H(8D) 0.9800

C(8B)-H(8E) 0.9800

C(8B)-H(8F) 0.9800

O(1S)-C(1S) 1.3185(16)

O(1S)-H(1S) 0.8400

O(2S)-C(1S) 1.2054(16)

C(1S)-C(2S) 1.5046(17)

C(2S)-H(2SA) 0.9800

C(2S)-H(2SB) 0.9800

C(2S)-H(2SC) 0.9800

C(1A)-N(1A)-C(6A) 120.54(10)

C(1A)-N(1A)-H(1A) 119.7

C(6A)-N(1A)-H(1A) 119.7

N(3A)-N(2A)-C(6A) 111.73(9)

N(3A)-N(2A)-C(3A) 123.60(9)

C(6A)-N(2A)-C(3A) 124.67(10)

C(4A)-N(3A)-N(2A) 103.79(9)

N(1A)-C(1A)-C(2A) 120.82(10)

N(1A)-C(1A)-C(7A) 115.68(10)

C(2A)-C(1A)-C(7A) 123.49(11)

C(1A)-C(2A)-C(3A) 122.36(11)

C(1A)-C(2A)-H(2A) 118.8

C(3A)-C(2A)-H(2A) 118.8

O(1A)-C(3A)-N(2A) 120.52(10)

O(1A)-C(3A)-C(2A) 126.57(11)

N(2A)-C(3A)-C(2A) 112.91(10)

N(3A)-C(4A)-C(5A) 113.11(10)

N(3A)-C(4A)-C(8A) 120.24(11)

C(5A)-C(4A)-C(8A) 126.65(11)

C(6A)-C(5A)-C(4A) 104.08(10)

C(6A)-C(5A)-H(5A) 128.0

C(4A)-C(5A)-H(5A) 128.0

N(1A)-C(6A)-C(5A) 134.03(11)

N(1A)-C(6A)-N(2A) 118.68(10)

C(5A)-C(6A)-N(2A) 107.29(10)

C(1A)-C(7A)-H(7A) 109.5

C(1A)-C(7A)-H(7B) 109.5

H(7A)-C(7A)-H(7B) 109.5

C(1A)-C(7A)-H(7C) 109.5

H(7A)-C(7A)-H(7C) 109.5

H(7B)-C(7A)-H(7C) 109.5

C(4A)-C(8A)-H(8A) 109.5

C(4A)-C(8A)-H(8B) 109.5

H(8A)-C(8A)-H(8B) 109.5

C(4A)-C(8A)-H(8C) 109.5

H(8A)-C(8A)-H(8C) 109.5

H(8B)-C(8A)-H(8C) 109.5

C(1B)-N(1B)-C(6B) 120.53(10)

C(1B)-N(1B)-H(1B) 119.7

C(6B)-N(1B)-H(1B) 119.7

N(3B)-N(2B)-C(6B) 111.29(9)

N(3B)-N(2B)-C(3B) 123.33(9)

C(6B)-N(2B)-C(3B) 125.32(10)

C(4B)-N(3B)-N(2B) 104.65(9)

N(1B)-C(1B)-C(2B) 120.63(10)

N(1B)-C(1B)-C(7B) 116.91(10)

C(2B)-C(1B)-C(7B) 122.45(10)

C(1B)-C(2B)-C(3B) 122.56(10)

C(1B)-C(2B)-H(2B) 118.7

C(3B)-C(2B)-H(2B) 118.7

O(1B)-C(3B)-N(2B) 119.08(11)

O(1B)-C(3B)-C(2B) 128.29(11)

N(2B)-C(3B)-C(2B) 112.62(10)

N(3B)-C(4B)-C(5B) 112.26(10)

N(3B)-C(4B)-C(8B) 119.64(10)

C(5B)-C(4B)-C(8B) 128.10(11)

C(6B)-C(5B)-C(4B) 104.53(10)

C(6B)-C(5B)-H(5B) 127.7

C(4B)-C(5B)-H(5B) 127.7

N(1B)-C(6B)-N(2B) 118.30(10)

N(1B)-C(6B)-C(5B) 134.44(10)

N(2B)-C(6B)-C(5B) 107.26(10)

C(1B)-C(7B)-H(7D) 109.5

C(1B)-C(7B)-H(7E) 109.5

H(7D)-C(7B)-H(7E) 109.5

C(1B)-C(7B)-H(7F) 109.5

H(7D)-C(7B)-H(7F) 109.5

H(7E)-C(7B)-H(7F) 109.5

C(4B)-C(8B)-H(8D) 109.5

C(4B)-C(8B)-H(8E) 109.5

H(8D)-C(8B)-H(8E) 109.5

C(4B)-C(8B)-H(8F) 109.5

H(8D)-C(8B)-H(8F) 109.5

H(8E)-C(8B)-H(8F) 109.5

C(1S)-O(1S)-H(1S) 109.5

O(2S)-C(1S)-O(1S) 123.94(11)

O(2S)-C(1S)-C(2S) 123.51(12)

O(1S)-C(1S)-C(2S) 112.54(11)

C(1S)-C(2S)-H(2SA) 109.5

C(1S)-C(2S)-H(2SB) 109.5

H(2SA)-C(2S)-H(2SB) 109.5

C(1S)-C(2S)-H(2SC) 109.5

H(2SA)-C(2S)-H(2SC) 109.5

H(2SB)-C(2S)-H(2SC) 109.5

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Table 4. Anisotropic displacement parameters (Å2x 103) for the compound 1. The anisotropic

displacement factor exponent takes the form: -22[ h2 a*2U11 + ... + 2 h k a* b* U12 ]

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U11U22U33U23U13U12

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O(1A)26(1) 31(1)21(1) 5(1)-2(1) 13(1)

N(1A)20(1) 24(1)20(1) 4(1)-2(1) 8(1)

N(2A)19(1) 23(1)20(1) 6(1)0(1) 9(1)

N(3A)21(1) 25(1)26(1) 8(1)3(1) 12(1)

C(1A)18(1) 24(1)24(1) 7(1)2(1) 8(1)

C(2A)21(1) 24(1)22(1) 5(1)2(1) 10(1)

C(3A)19(1) 23(1)21(1) 6(1)2(1) 8(1)

C(4A)22(1) 24(1)27(1) 8(1)5(1) 10(1)

C(5A)23(1) 24(1)23(1) 4(1)2(1) 8(1)

C(6A)16(1) 24(1)20(1) 6(1)2(1) 6(1)

C(7A)27(1) 28(1)28(1) 8(1)-2(1) 14(1)

C(8A)33(1) 25(1)31(1) 7(1)7(1) 14(1)

O(1B)24(1) 32(1)22(1) 5(1)-2(1) 13(1)

N(1B)19(1) 22(1)21(1) 5(1)-1(1) 9(1)

N(2B)19(1) 22(1)20(1) 6(1)1(1) 9(1)

N(3B)23(1) 22(1)24(1) 6(1)2(1) 9(1)

C(1B)21(1) 22(1)22(1) 4(1)3(1) 8(1)

C(2B)21(1) 23(1)22(1) 2(1)0(1) 8(1)

C(3B)19(1) 26(1)18(1) 4(1)3(1) 8(1)

C(4B)22(1) 24(1)24(1) 6(1)3(1) 9(1)

C(5B)21(1) 23(1)23(1) 4(1)0(1) 8(1)

C(6B)18(1) 23(1)19(1) 5(1)1(1) 8(1)

C(7B)28(1) 22(1)33(1) 3(1)-3(1) 10(1)

C(8B)32(1) 24(1)35(1) 5(1)2(1) 11(1)

O(1S)30(1) 36(1)31(1) 16(1)6(1) 18(1)

O(2S)36(1) 44(1)44(1) 20(1)15(1) 20(1)

C(1S)27(1) 22(1)23(1) 3(1)-1(1) 7(1)

C(2S)41(1) 32(1)31(1) 11(1)-1(1) 15(1)

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Table 5. Hydrogen coordinates ( x 104) and isotropic displacement parameters (Å2x 10 3)

for the compound 1.

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xy z U(eq)

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H(1A) 1430 9864 3542 26

H(2A) 2960 12233 6915 26

H(5A) 2325 7450 3326 28

H(7A) 132 11585 4232 41

H(7B) 1804 12430 3877 41

H(7C) 1364 12842 5239 41

H(8A) 4310 6008 4165 43

H(8B) 3375 5562 5302 43

H(8C) 5249 6453 5624 43

H(1B) 4051 152 1206 25

H(2B) 355 -1401 -1671 27

H(5B) 4916 3021 2042 27

H(7D) 2581 -2224 862 42

H(7E) 3275 -2280 -443 42

H(7F) 1366 -2861 -482 42

H(8D) 2850 5357 1596 45

H(8E) 3815 5591 437 45

H(8F) 4736 5502 1811 45

H(1S) 842 3735 -1282 45

H(2SA) -365 5966 -2579 51

H(2SB) -485 5072 -3933 51

H(2SC) 1056 6384 -3382 51

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Table 6. Torsion angles [°] for the compound 1.

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C(6A)-N(2A)-N(3A)-C(4A)-0.22(13)

C(3A)-N(2A)-N(3A)-C(4A)179.71(11)

C(6A)-N(1A)-C(1A)-C(2A)-0.39(18)

C(6A)-N(1A)-C(1A)-C(7A)178.48(10)

N(1A)-C(1A)-C(2A)-C(3A)1.47(18)

C(7A)-C(1A)-C(2A)-C(3A)-177.31(11)

N(3A)-N(2A)-C(3A)-O(1A)0.83(18)

C(6A)-N(2A)-C(3A)-O(1A)-179.25(11)

N(3A)-N(2A)-C(3A)-C(2A)-178.95(10)

C(6A)-N(2A)-C(3A)-C(2A)0.96(16)

C(1A)-C(2A)-C(3A)-O(1A)178.56(12)

C(1A)-C(2A)-C(3A)-N(2A)-1.67(16)

N(2A)-N(3A)-C(4A)-C(5A)0.03(13)

N(2A)-N(3A)-C(4A)-C(8A)-179.30(11)

N(3A)-C(4A)-C(5A)-C(6A)0.16(14)

C(8A)-C(4A)-C(5A)-C(6A)179.43(12)

C(1A)-N(1A)-C(6A)-C(5A)179.13(13)

C(1A)-N(1A)-C(6A)-N(2A)-0.32(16)

C(4A)-C(5A)-C(6A)-N(1A)-179.77(13)

C(4A)-C(5A)-C(6A)-N(2A)-0.28(13)

N(3A)-N(2A)-C(6A)-N(1A)179.91(9)

C(3A)-N(2A)-C(6A)-N(1A)-0.02(17)

N(3A)-N(2A)-C(6A)-C(5A)0.32(13)

C(3A)-N(2A)-C(6A)-C(5A)-179.60(11)

C(6B)-N(2B)-N(3B)-C(4B)0.84(13)

C(3B)-N(2B)-N(3B)-C(4B)178.44(10)

C(6B)-N(1B)-C(1B)-C(2B)2.11(17)

C(6B)-N(1B)-C(1B)-C(7B)-177.20(10)

N(1B)-C(1B)-C(2B)-C(3B)-1.32(18)

C(7B)-C(1B)-C(2B)-C(3B)177.95(11)

N(3B)-N(2B)-C(3B)-O(1B)0.77(17)

C(6B)-N(2B)-C(3B)-O(1B)178.03(10)

N(3B)-N(2B)-C(3B)-C(2B)-177.97(10)

C(6B)-N(2B)-C(3B)-C(2B)-0.71(16)

C(1B)-C(2B)-C(3B)-O(1B)-178.01(12)

C(1B)-C(2B)-C(3B)-N(2B)0.58(16)

N(2B)-N(3B)-C(4B)-C(5B)-0.52(13)

N(2B)-N(3B)-C(4B)-C(8B)178.95(11)

N(3B)-C(4B)-C(5B)-C(6B)0.02(14)

C(8B)-C(4B)-C(5B)-C(6B)-179.39(13)

C(1B)-N(1B)-C(6B)-N(2B)-2.16(16)

C(1B)-N(1B)-C(6B)-C(5B)177.72(13)

N(3B)-N(2B)-C(6B)-N(1B)179.06(9)

C(3B)-N(2B)-C(6B)-N(1B)1.52(17)

N(3B)-N(2B)-C(6B)-C(5B)-0.85(13)

C(3B)-N(2B)-C(6B)-C(5B)-178.40(11)

C(4B)-C(5B)-C(6B)-N(1B)-179.40(13)

C(4B)-C(5B)-C(6B)-N(2B)0.49(13)

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