Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008622/bt2024sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008622/bt2024Isup2.hkl |
CCDC reference: 605233
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.083
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 34 Perc. PLAT230_ALERT_2_B Hirshfeld Test Diff for N12 - C16 .. 7.17 su
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C6 .. 5.72 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C9 .. 6.17 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C3 .. 5.83 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2003).
C17H32N4 | Z = 2 |
Mr = 292.47 | F(000) = 324 |
Triclinic, P1 | Dx = 1.027 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.257 (2) Å | Cell parameters from 6881 reflections |
b = 11.719 (3) Å | θ = 3.1–25.2° |
c = 13.392 (5) Å | µ = 0.06 mm−1 |
α = 90.450 (13)° | T = 291 K |
β = 101.719 (8)° | Block, colourless |
γ = 100.067 (15)° | 0.20 × 0.15 × 0.15 mm |
V = 945.7 (5) Å3 |
Nonius KappaCCD diffractometer | 1123 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 25.2°, θmin = 3.1° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −7→7 |
498 frames via ω–rotation (Δω=1°) and two times 60 s per frame (four sets at different κ–angles) scans | k = −13→14 |
6681 measured reflections | l = −15→15 |
3297 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 1.01 | w = [exp{4.20(sinθ/λ)2}]/[σ2(Fo2)] |
3297 reflections | (Δ/σ)max = 0.001 |
190 parameters | Δρmax = 0.09 e Å−3 |
0 restraints | Δρmin = −0.11 e Å−3 |
Experimental. 1H NMR (500 MHz, CDCl3): δ 1.43 (s, 9H), 1.72 (s, 3H), 2.29 (4H), 2.83 (s, 2H). 3.39 (t, 4H, J = 4.7 Hz), 4.83 (s, 2H), 4.84 (s, 2H); 13C NMR (125 MHz, CDCl3): δ 20.8 (CH3), 28.4 (CH3), 50.7 (CH2), 52.9 (CH2), 65.3 (CH2), 79.4 (Cq), 113.1 (CH2), 142.4 (Cq), 154.8 (Cq); IR (KBr plate), ν (cm-1): 897 (m), 1009 (m), 1122 (s), 1168 (s), 1244 (s), 1362 (m), 1419 (s), 1696 (vs), 2801 (m), 2940 (s), 2980 (m); MS (FAB+ LR), m/z (%): (M)+, 240.0?(65); exact mass (FAB + HR): (M)+, 240.1852 ?(85) (calculated for C13H24N2O2: 240.1838). 1H NMR (500 MHz, CDCl3): δ 1.48 (s, 1H), 1.64 (s, 3H), 2.0–2.5 (4H), 2.74 (s, 2H), 2.77 (4H), 4.74 (s, 2H), 4.77 (s, 2H); 13C NMR (125 MHz, CDCl3): δ 20.7 (CH3), 46.0 (CH2), 54.5 (CH2), 65.8 (CH2), 112.6 (CH2), 142.5 (Cq); IR (KBr plate), ν (cm-1): 805 (m), 896 (s), 1014 (m), 1142 (s), 1370 (m), 1455 (s), 1651 (m), 2805 (s), 2940 (s), 2968 (s), 3073 (m) 3283 (w); MS (FAB+ LR), m/z (%): 141.1 (M + H+), (25); exact mass (FAB + HR): 141.1416 (M + H+), (100) (calculated for C8H17N2: 141.1392). 1H NMR (500 MHz, CDCl3): δ 1.71 (s, 3H), 2.28–2.60 (16H), 2.84 (s, 4H), 2.9 (s, 2H), 4.81 (s, 2H), 4.84 (s, 2H); 13C NMR (125 MHz, CDCl3): δ 20.9 (CH3), 51.6 (CH2), 53.2 (CH2), 65.4 (CH2), 81.1 (CH2), 112.7 (CH2), 142.8 (Cq); IR (KBr plate), ν (cm-1): 831 (m), 899 (vs), 1012 (s), 1049 (m), 1119 (m), 1147 (vs), 1166 (s), 1282 (s), 1342 (m), 1371 (m), 1456 (s), 1647 (m), 2758 (m), 2802 (s), 2939 (s), 2964 (s), 3074 (w); MS (FAB + LR), m/z (%): 291.4 (M + H+), (15); exact mass (FAB + HR): 291.2563 (M - H+), (100) (calculated for C17H31N4: 291.2548). |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.3971 (3) | 1.20091 (14) | 0.61737 (13) | 0.0596 (5) | |
N2 | 0.3116 (2) | 1.01685 (13) | 0.75165 (13) | 0.0527 (5) | |
N11 | −0.1595 (2) | 0.68818 (13) | 0.90323 (13) | 0.0544 (5) | |
N12 | 0.1055 (2) | 0.90230 (12) | 0.86038 (12) | 0.0502 (5) | |
C1 | 0.7059 (4) | 1.2833 (2) | 0.4303 (2) | 0.1042 (9) | |
H1A | 0.8448 | 1.3225 | 0.4238 | 0.125* | |
H1B | 0.6301 | 1.2234 | 0.3837 | 0.125* | |
C2 | 0.7310 (4) | 1.40858 (19) | 0.5829 (2) | 0.1124 (10) | |
H2A | 0.8735 | 1.4407 | 0.5691 | 0.169* | |
H2B | 0.7499 | 1.3783 | 0.6499 | 0.169* | |
H2C | 0.6423 | 1.4681 | 0.5794 | 0.169* | |
C3 | 0.6170 (4) | 1.3126 (2) | 0.5051 (2) | 0.0730 (7) | |
C4 | 0.3933 (3) | 1.24962 (19) | 0.51690 (17) | 0.0826 (8) | |
H4A | 0.2892 | 1.3029 | 0.5061 | 0.099* | |
H4B | 0.3410 | 1.1874 | 0.4648 | 0.099* | |
C5 | 0.1726 (3) | 1.15719 (18) | 0.63186 (17) | 0.0749 (7) | |
H5A | 0.0997 | 1.0963 | 0.5805 | 0.090* | |
H5B | 0.0873 | 1.2193 | 0.6241 | 0.090* | |
C6 | 0.1820 (3) | 1.11001 (17) | 0.73703 (17) | 0.0686 (7) | |
H6A | 0.2484 | 1.1721 | 0.7882 | 0.082* | |
H6B | 0.0325 | 1.0807 | 0.7460 | 0.082* | |
C7 | 0.5355 (3) | 1.06116 (16) | 0.73701 (16) | 0.0643 (6) | |
H7A | 0.6220 | 0.9995 | 0.7452 | 0.077* | |
H7B | 0.6077 | 1.1226 | 0.7879 | 0.077* | |
C8 | 0.5246 (3) | 1.10713 (17) | 0.63196 (16) | 0.0675 (7) | |
H8A | 0.6738 | 1.1354 | 0.6222 | 0.081* | |
H8B | 0.4561 | 1.0448 | 0.5813 | 0.081* | |
C9 | 0.3204 (3) | 0.96918 (16) | 0.85167 (16) | 0.0608 (6) | |
H9A | 0.3646 | 1.0319 | 0.9035 | 0.073* | |
H9B | 0.4311 | 0.9195 | 0.8636 | 0.073* | |
C11 | −0.6125 (4) | 0.47358 (19) | 0.7867 (2) | 0.0988 (9) | |
H11A | −0.6439 | 0.4026 | 0.7504 | 0.119* | |
H11B | −0.7138 | 0.5239 | 0.7757 | 0.119* | |
C12 | −0.2518 (4) | 0.42637 (17) | 0.87620 (18) | 0.0926 (8) | |
H12A | −0.2998 | 0.3576 | 0.8323 | 0.139* | |
H12B | −0.2331 | 0.4053 | 0.9462 | 0.139* | |
H12C | −0.1131 | 0.4671 | 0.8640 | 0.139* | |
C13 | −0.4226 (4) | 0.50311 (19) | 0.85455 (18) | 0.0674 (7) | |
C14 | −0.3672 (3) | 0.61601 (16) | 0.91652 (16) | 0.0663 (6) | |
H14A | −0.4873 | 0.6589 | 0.8969 | 0.080* | |
H14B | −0.3556 | 0.5997 | 0.9881 | 0.080* | |
C15 | −0.1805 (3) | 0.72908 (16) | 0.79939 (15) | 0.0597 (6) | |
H15A | −0.2968 | 0.7752 | 0.7858 | 0.072* | |
H15B | −0.2207 | 0.6632 | 0.7508 | 0.072* | |
C16 | 0.0372 (3) | 0.80158 (16) | 0.78711 (15) | 0.0585 (6) | |
H16A | 0.1514 | 0.7540 | 0.7975 | 0.070* | |
H16B | 0.0217 | 0.8285 | 0.7181 | 0.070* | |
C17 | 0.1222 (3) | 0.86266 (15) | 0.96475 (15) | 0.0571 (6) | |
H17A | 0.1584 | 0.9292 | 1.0126 | 0.069* | |
H17B | 0.2401 | 0.8177 | 0.9804 | 0.069* | |
C18 | −0.0957 (3) | 0.78876 (16) | 0.97590 (15) | 0.0601 (6) | |
H18A | −0.0816 | 0.7621 | 1.0449 | 0.072* | |
H18B | −0.2113 | 0.8355 | 0.9645 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0492 (11) | 0.0679 (12) | 0.0641 (14) | 0.0111 (9) | 0.0162 (10) | 0.0240 (10) |
N2 | 0.0458 (11) | 0.0518 (11) | 0.0606 (14) | 0.0063 (8) | 0.0127 (9) | 0.0157 (9) |
N11 | 0.0650 (12) | 0.0469 (11) | 0.0523 (13) | 0.0031 (9) | 0.0205 (10) | 0.0065 (10) |
N12 | 0.0546 (11) | 0.0454 (10) | 0.0466 (12) | 0.0004 (8) | 0.0087 (9) | 0.0033 (9) |
C1 | 0.095 (2) | 0.141 (2) | 0.075 (2) | 0.0075 (17) | 0.0272 (17) | 0.0267 (19) |
C2 | 0.127 (2) | 0.089 (2) | 0.120 (3) | −0.0124 (16) | 0.051 (2) | 0.0069 (19) |
C3 | 0.0695 (17) | 0.0866 (19) | 0.0661 (19) | 0.0138 (14) | 0.0203 (15) | 0.0315 (15) |
C4 | 0.0743 (18) | 0.1015 (19) | 0.072 (2) | 0.0124 (13) | 0.0161 (14) | 0.0354 (15) |
C5 | 0.0529 (15) | 0.0886 (17) | 0.086 (2) | 0.0164 (12) | 0.0175 (14) | 0.0319 (14) |
C6 | 0.0534 (14) | 0.0748 (16) | 0.0833 (19) | 0.0140 (12) | 0.0244 (13) | 0.0262 (14) |
C7 | 0.0540 (14) | 0.0650 (15) | 0.0788 (19) | 0.0149 (11) | 0.0209 (13) | 0.0221 (13) |
C8 | 0.0623 (15) | 0.0684 (15) | 0.0781 (19) | 0.0114 (12) | 0.0290 (14) | 0.0152 (13) |
C9 | 0.0549 (14) | 0.0538 (13) | 0.0694 (18) | 0.0034 (10) | 0.0083 (12) | 0.0117 (12) |
C11 | 0.092 (2) | 0.0824 (18) | 0.108 (2) | −0.0106 (14) | 0.0114 (18) | 0.0112 (16) |
C12 | 0.115 (2) | 0.0598 (16) | 0.104 (2) | 0.0133 (14) | 0.0266 (17) | 0.0098 (15) |
C13 | 0.0734 (17) | 0.0551 (15) | 0.0726 (19) | −0.0044 (13) | 0.0256 (15) | 0.0144 (14) |
C14 | 0.0707 (15) | 0.0571 (14) | 0.0740 (17) | 0.0012 (11) | 0.0306 (13) | 0.0122 (13) |
C15 | 0.0670 (15) | 0.0541 (14) | 0.0558 (16) | 0.0019 (11) | 0.0154 (12) | 0.0049 (12) |
C16 | 0.0667 (15) | 0.0579 (14) | 0.0499 (15) | 0.0035 (11) | 0.0165 (12) | 0.0079 (12) |
C17 | 0.0657 (15) | 0.0539 (14) | 0.0497 (16) | 0.0080 (11) | 0.0099 (12) | 0.0043 (11) |
C18 | 0.0718 (15) | 0.0597 (14) | 0.0522 (15) | 0.0117 (11) | 0.0204 (12) | 0.0077 (12) |
N1—C8 | 1.459 (2) | C7—C8 | 1.503 (3) |
N1—C5 | 1.461 (2) | C7—H7A | 0.9700 |
N1—C4 | 1.463 (2) | C7—H7B | 0.9700 |
N2—C9 | 1.450 (2) | C8—H8A | 0.9700 |
N2—C7 | 1.459 (2) | C8—H8B | 0.9700 |
N2—C6 | 1.462 (2) | C9—H9A | 0.9700 |
N11—C15 | 1.463 (2) | C9—H9B | 0.9700 |
N11—C14 | 1.465 (2) | C11—C13 | 1.330 (3) |
N11—C18 | 1.468 (2) | C11—H11A | 0.9300 |
N12—C9 | 1.460 (2) | C11—H11B | 0.9300 |
N12—C17 | 1.466 (2) | C12—C13 | 1.500 (3) |
N12—C16 | 1.474 (2) | C12—H12A | 0.9600 |
C1—C3 | 1.311 (3) | C12—H12B | 0.9600 |
C1—H1A | 0.9300 | C12—H12C | 0.9600 |
C1—H1B | 0.9300 | C13—C14 | 1.505 (3) |
C2—C3 | 1.503 (3) | C14—H14A | 0.9700 |
C2—H2A | 0.9600 | C14—H14B | 0.9700 |
C2—H2B | 0.9600 | C15—C16 | 1.514 (2) |
C2—H2C | 0.9600 | C15—H15A | 0.9700 |
C3—C4 | 1.503 (3) | C15—H15B | 0.9700 |
C4—H4A | 0.9700 | C16—H16A | 0.9700 |
C4—H4B | 0.9700 | C16—H16B | 0.9700 |
C5—C6 | 1.511 (3) | C17—C18 | 1.518 (2) |
C5—H5A | 0.9700 | C17—H17A | 0.9700 |
C5—H5B | 0.9700 | C17—H17B | 0.9700 |
C6—H6A | 0.9700 | C18—H18A | 0.9700 |
C6—H6B | 0.9700 | C18—H18B | 0.9700 |
C8—N1—C5 | 108.91 (16) | N1—C8—H8B | 109.4 |
C8—N1—C4 | 111.63 (18) | C7—C8—H8B | 109.4 |
C5—N1—C4 | 111.16 (17) | H8A—C8—H8B | 108.0 |
C9—N2—C7 | 110.17 (15) | N2—C9—N12 | 111.33 (16) |
C9—N2—C6 | 112.05 (17) | N2—C9—H9A | 109.4 |
C7—N2—C6 | 109.13 (15) | N12—C9—H9A | 109.4 |
C15—N11—C14 | 110.91 (16) | N2—C9—H9B | 109.4 |
C15—N11—C18 | 109.00 (15) | N12—C9—H9B | 109.4 |
C14—N11—C18 | 110.93 (16) | H9A—C9—H9B | 108.0 |
C9—N12—C17 | 108.54 (16) | C13—C11—H11A | 120.0 |
C9—N12—C16 | 111.43 (16) | C13—C11—H11B | 120.0 |
C17—N12—C16 | 109.73 (15) | H11A—C11—H11B | 120.0 |
C3—C1—H1A | 120.0 | C13—C12—H12A | 109.5 |
C3—C1—H1B | 120.0 | C13—C12—H12B | 109.5 |
H1A—C1—H1B | 120.0 | H12A—C12—H12B | 109.5 |
C3—C2—H2A | 109.5 | C13—C12—H12C | 109.5 |
C3—C2—H2B | 109.5 | H12A—C12—H12C | 109.5 |
H2A—C2—H2B | 109.5 | H12B—C12—H12C | 109.5 |
C3—C2—H2C | 109.5 | C11—C13—C12 | 122.9 (2) |
H2A—C2—H2C | 109.5 | C11—C13—C14 | 121.7 (2) |
H2B—C2—H2C | 109.5 | C12—C13—C14 | 115.4 (2) |
C1—C3—C2 | 122.6 (2) | N11—C14—C13 | 112.95 (17) |
C1—C3—C4 | 120.6 (3) | N11—C14—H14A | 109.0 |
C2—C3—C4 | 116.8 (2) | C13—C14—H14A | 109.0 |
N1—C4—C3 | 112.84 (19) | N11—C14—H14B | 109.0 |
N1—C4—H4A | 109.0 | C13—C14—H14B | 109.0 |
C3—C4—H4A | 109.0 | H14A—C14—H14B | 107.8 |
N1—C4—H4B | 109.0 | N11—C15—C16 | 109.88 (17) |
C3—C4—H4B | 109.0 | N11—C15—H15A | 109.7 |
H4A—C4—H4B | 107.8 | C16—C15—H15A | 109.7 |
N1—C5—C6 | 109.86 (17) | N11—C15—H15B | 109.7 |
N1—C5—H5A | 109.7 | C16—C15—H15B | 109.7 |
C6—C5—H5A | 109.7 | H15A—C15—H15B | 108.2 |
N1—C5—H5B | 109.7 | N12—C16—C15 | 111.46 (17) |
C6—C5—H5B | 109.7 | N12—C16—H16A | 109.3 |
H5A—C5—H5B | 108.2 | C15—C16—H16A | 109.3 |
N2—C6—C5 | 111.09 (18) | N12—C16—H16B | 109.3 |
N2—C6—H6A | 109.4 | C15—C16—H16B | 109.3 |
C5—C6—H6A | 109.4 | H16A—C16—H16B | 108.0 |
N2—C6—H6B | 109.4 | N12—C17—C18 | 110.20 (17) |
C5—C6—H6B | 109.4 | N12—C17—H17A | 109.6 |
H6A—C6—H6B | 108.0 | C18—C17—H17A | 109.6 |
N2—C7—C8 | 109.67 (17) | N12—C17—H17B | 109.6 |
N2—C7—H7A | 109.7 | C18—C17—H17B | 109.6 |
C8—C7—H7A | 109.7 | H17A—C17—H17B | 108.1 |
N2—C7—H7B | 109.7 | N11—C18—C17 | 111.48 (16) |
C8—C7—H7B | 109.7 | N11—C18—H18A | 109.3 |
H7A—C7—H7B | 108.2 | C17—C18—H18A | 109.3 |
N1—C8—C7 | 111.17 (18) | N11—C18—H18B | 109.3 |
N1—C8—H8A | 109.4 | C17—C18—H18B | 109.3 |
C7—C8—H8A | 109.4 | H18A—C18—H18B | 108.0 |
C8—N1—C4—C3 | −67.4 (2) | C17—N12—C9—N2 | −176.62 (15) |
C5—N1—C4—C3 | 170.77 (19) | C16—N12—C9—N2 | 62.4 (2) |
C1—C3—C4—N1 | 124.0 (2) | C15—N11—C14—C13 | 67.0 (2) |
C2—C3—C4—N1 | −55.6 (3) | C18—N11—C14—C13 | −171.69 (17) |
C8—N1—C5—C6 | 57.9 (2) | C11—C13—C14—N11 | −122.4 (2) |
C4—N1—C5—C6 | −178.73 (18) | C12—C13—C14—N11 | 58.7 (2) |
C9—N2—C6—C5 | −179.23 (16) | C14—N11—C15—C16 | −179.00 (16) |
C7—N2—C6—C5 | 58.5 (2) | C18—N11—C15—C16 | 58.6 (2) |
N1—C5—C6—N2 | −58.7 (2) | C9—N12—C16—C15 | 177.38 (17) |
C9—N2—C7—C8 | 178.34 (17) | C17—N12—C16—C15 | 57.1 (2) |
C6—N2—C7—C8 | −58.2 (2) | N11—C15—C16—N12 | −58.9 (2) |
C5—N1—C8—C7 | −59.3 (2) | C9—N12—C17—C18 | −177.85 (15) |
C4—N1—C8—C7 | 177.59 (16) | C16—N12—C17—C18 | −55.9 (2) |
N2—C7—C8—N1 | 59.9 (2) | C15—N11—C18—C17 | −59.0 (2) |
C7—N2—C9—N12 | −167.72 (16) | C14—N11—C18—C17 | 178.57 (17) |
C6—N2—C9—N12 | 70.6 (2) | N12—C17—C18—N11 | 58.1 (2) |