Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032661/bt2171sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032661/bt2171IIsup2.hkl |
CCDC reference: 620700
Data collection: KM-4 Software (Kuma, 1993); cell refinement: KM-4 Software; data reduction: DATAPROC (Gałdecki et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) ORTEP-3 (Version 1.062; Farrugia, 1997) and Mercury (Version 1.4; Macrae et al., 2006); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
C17H17N3O2 | Z = 2 |
Mr = 295.34 | F(000) = 312 |
Triclinic, P1 | Dx = 1.290 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54178 Å |
a = 4.701 (1) Å | Cell parameters from 99 reflections |
b = 12.415 (2) Å | θ = 4–50° |
c = 14.083 (3) Å | µ = 0.70 mm−1 |
α = 110.77 (3)° | T = 291 K |
β = 93.16 (3)° | Prism, colourless |
γ = 96.04 (3)° | 0.35 × 0.31 × 0.27 mm |
V = 760.5 (3) Å3 |
Kuma KM-4 diffractometer | 2835 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 80.7°, θmin = 3.4° |
ω–2θ scans | h = −5→5 |
Absorption correction: ψ scan (North et al., 1968) | k = −7→15 |
Tmin = 0.784, Tmax = 0.820 | l = −17→16 |
3332 measured reflections | 3 standard reflections every 100 reflections |
3191 independent reflections | intensity decay: 11.2% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: mixed |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.077P)2 + 0.1995P] where P = (Fo2 + 2Fc2)/3 |
3191 reflections | (Δ/σ)max < 0.001 |
199 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Experimental. For (I): 1H NMR (DMSO/TMS, p.p.m.): 2.35 (s, 6H, 2CH3), 4.45 (s, 4H, 2CH2), 7.45 (s, 2H, Har), 9.75 (s, 2H, 2NHCO). For (II): 1H NMR (DMSO/TMS, p.p.m.): 3.21 (broad, 1H, NHCH2), 3.6 (s, 2H) 3.75 (s, 2H, CH2CO), 4.50 (s, 2H, NCH2Ph), 7.25 (m, 9H, Har), 10.00 (broad, 1H, NHCO). |
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 | Occ. (<1) | |
N1 | 0.4465 (3) | 0.46485 (11) | 0.26107 (9) | 0.0411 (3) | |
O1 | 0.0468 (3) | 0.60225 (11) | 0.12859 (9) | 0.0595 (4) | |
O11 | 0.2272 (3) | 0.53381 (10) | 0.40433 (9) | 0.0605 (4) | |
N2 | 0.2493 (3) | 0.43696 (11) | 0.06757 (10) | 0.0469 (3) | |
H2N | 0.1514 | 0.4216 | 0.0080 | 0.056* | |
N3 | 0.1126 (3) | 0.32776 (11) | 0.42530 (9) | 0.0444 (3) | |
H3N | 0.0938 | 0.3986 | 0.4713 | 0.053* | |
C1 | 0.5428 (3) | 0.37455 (13) | 0.17962 (11) | 0.0392 (3) | |
C2 | 0.7312 (4) | 0.30156 (15) | 0.19305 (12) | 0.0472 (4) | |
H2 | 0.8084 | 0.3115 | 0.2583 | 0.057* | |
C3 | 0.8046 (4) | 0.21369 (17) | 0.10903 (14) | 0.0566 (4) | |
H3 | 0.9268 | 0.1632 | 0.1183 | 0.068* | |
C4 | 0.6979 (4) | 0.20048 (17) | 0.01168 (14) | 0.0592 (5) | |
H4 | 0.7476 | 0.1411 | −0.0444 | 0.071* | |
C5 | 0.5179 (4) | 0.27530 (15) | −0.00244 (12) | 0.0517 (4) | |
H5 | 0.4490 | 0.2672 | −0.0681 | 0.062* | |
C6 | 0.4390 (3) | 0.36271 (13) | 0.08095 (11) | 0.0420 (3) | |
C7 | 0.2157 (4) | 0.53793 (13) | 0.14071 (12) | 0.0456 (4) | |
C8 | 0.4070 (4) | 0.56881 (13) | 0.23882 (12) | 0.0485 (4) | |
H8A | 0.5924 | 0.6071 | 0.2330 | 0.058* | |
H8B | 0.3214 | 0.6225 | 0.2945 | 0.058* | |
C11 | 0.3340 (3) | 0.45355 (13) | 0.34560 (10) | 0.0411 (3) | |
C12 | 0.3461 (3) | 0.34270 (13) | 0.36611 (11) | 0.0422 (3) | |
H12A | 0.3291 | 0.2771 | 0.3021 | 0.051* | |
H12B | 0.5289 | 0.3465 | 0.4035 | 0.051* | |
C13 | 0.1512 (5) | 0.24340 (15) | 0.47346 (12) | 0.0554 (4) | |
H13A | 0.0177 | 0.2518 | 0.5249 | 0.067* | |
H13B | 0.3445 | 0.2603 | 0.5076 | 0.067* | |
C14 | 0.1048 (4) | 0.11929 (15) | 0.39918 (13) | 0.0503 (4) | |
C17 | 0.0146 (7) | −0.1107 (2) | 0.2654 (2) | 0.0886 (8) | |
H17 | −0.0175 | −0.1874 | 0.2201 | 0.106* | |
C15' | −0.041 (2) | 0.0839 (7) | 0.3020 (6) | 0.0552 (16) | 0.480 (17) |
H15' | −0.1176 | 0.1395 | 0.2818 | 0.066* | 0.480 (17) |
C16' | −0.078 (2) | −0.0291 (7) | 0.2348 (7) | 0.072 (2) | 0.480 (17) |
H16' | −0.1655 | −0.0486 | 0.1690 | 0.086* | 0.480 (17) |
C18' | 0.143 (3) | −0.0844 (7) | 0.3605 (9) | 0.085 (2) | 0.480 (17) |
H18' | 0.2015 | −0.1430 | 0.3805 | 0.103* | 0.480 (17) |
C19' | 0.187 (2) | 0.0299 (5) | 0.4283 (6) | 0.0656 (19) | 0.480 (17) |
H19' | 0.2726 | 0.0471 | 0.4941 | 0.079* | 0.480 (17) |
C15 | −0.125 (2) | 0.0841 (7) | 0.3299 (9) | 0.070 (2) | 0.520 (17) |
H15 | −0.2481 | 0.1365 | 0.3260 | 0.085* | 0.520 (17) |
C16 | −0.177 (3) | −0.0309 (8) | 0.2637 (9) | 0.092 (3) | 0.520 (17) |
H16 | −0.3414 | −0.0559 | 0.2175 | 0.110* | 0.520 (17) |
C18 | 0.249 (2) | −0.0711 (8) | 0.3364 (9) | 0.093 (2) | 0.520 (17) |
H18 | 0.3755 | −0.1223 | 0.3410 | 0.111* | 0.520 (17) |
C19 | 0.302 (2) | 0.0446 (5) | 0.4016 (7) | 0.0728 (18) | 0.520 (17) |
H19 | 0.4686 | 0.0717 | 0.4466 | 0.087* | 0.520 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0510 (8) | 0.0380 (6) | 0.0337 (6) | 0.0102 (5) | 0.0050 (5) | 0.0110 (5) |
O1 | 0.0833 (9) | 0.0519 (7) | 0.0505 (7) | 0.0265 (6) | 0.0074 (6) | 0.0225 (5) |
O11 | 0.0917 (10) | 0.0418 (6) | 0.0484 (7) | 0.0205 (6) | 0.0270 (6) | 0.0107 (5) |
N2 | 0.0609 (9) | 0.0457 (7) | 0.0354 (6) | 0.0132 (6) | 0.0033 (5) | 0.0148 (5) |
N3 | 0.0569 (8) | 0.0424 (7) | 0.0361 (6) | 0.0138 (6) | 0.0106 (5) | 0.0140 (5) |
C1 | 0.0403 (8) | 0.0397 (7) | 0.0357 (7) | 0.0066 (6) | 0.0059 (5) | 0.0107 (6) |
C2 | 0.0445 (9) | 0.0535 (9) | 0.0443 (8) | 0.0132 (7) | 0.0060 (6) | 0.0163 (7) |
C3 | 0.0554 (11) | 0.0586 (10) | 0.0576 (10) | 0.0254 (8) | 0.0126 (8) | 0.0173 (8) |
C4 | 0.0684 (12) | 0.0570 (10) | 0.0483 (9) | 0.0220 (9) | 0.0181 (8) | 0.0087 (8) |
C5 | 0.0624 (11) | 0.0537 (9) | 0.0365 (7) | 0.0121 (8) | 0.0093 (7) | 0.0114 (7) |
C6 | 0.0476 (9) | 0.0413 (7) | 0.0380 (7) | 0.0079 (6) | 0.0072 (6) | 0.0144 (6) |
C7 | 0.0616 (10) | 0.0388 (7) | 0.0418 (7) | 0.0105 (7) | 0.0108 (7) | 0.0196 (6) |
C8 | 0.0646 (10) | 0.0370 (7) | 0.0425 (8) | 0.0077 (7) | 0.0054 (7) | 0.0126 (6) |
C11 | 0.0482 (9) | 0.0390 (7) | 0.0323 (6) | 0.0072 (6) | 0.0034 (6) | 0.0080 (5) |
C12 | 0.0476 (9) | 0.0442 (8) | 0.0352 (7) | 0.0124 (6) | 0.0044 (6) | 0.0132 (6) |
C13 | 0.0809 (13) | 0.0517 (9) | 0.0382 (8) | 0.0133 (8) | 0.0079 (8) | 0.0202 (7) |
C14 | 0.0615 (11) | 0.0476 (9) | 0.0486 (9) | 0.0132 (7) | 0.0129 (7) | 0.0230 (7) |
C17 | 0.116 (2) | 0.0470 (11) | 0.0933 (19) | 0.0091 (12) | 0.0246 (16) | 0.0120 (11) |
C15' | 0.071 (5) | 0.046 (2) | 0.049 (3) | 0.013 (3) | 0.006 (2) | 0.015 (2) |
C16' | 0.092 (6) | 0.049 (3) | 0.062 (3) | 0.003 (3) | 0.015 (3) | 0.007 (2) |
C18' | 0.106 (7) | 0.055 (3) | 0.115 (6) | 0.030 (4) | 0.029 (5) | 0.047 (3) |
C19' | 0.076 (5) | 0.065 (3) | 0.073 (3) | 0.025 (3) | 0.010 (3) | 0.040 (2) |
C15 | 0.071 (5) | 0.052 (2) | 0.082 (6) | 0.013 (3) | 0.000 (3) | 0.018 (3) |
C16 | 0.095 (6) | 0.067 (3) | 0.093 (6) | −0.008 (4) | −0.013 (4) | 0.013 (4) |
C18 | 0.095 (6) | 0.066 (4) | 0.128 (6) | 0.039 (4) | 0.040 (4) | 0.035 (4) |
C19 | 0.068 (4) | 0.066 (3) | 0.090 (4) | 0.017 (2) | 0.010 (3) | 0.031 (3) |
N1—C11 | 1.3743 (19) | C12—H12B | 0.9700 |
N1—C1 | 1.4247 (18) | C13—C14 | 1.509 (2) |
N1—C8 | 1.4593 (19) | C13—H13A | 0.9700 |
O1—C7 | 1.230 (2) | C13—H13B | 0.9700 |
O11—C11 | 1.2230 (19) | C14—C15 | 1.337 (10) |
N2—C7 | 1.342 (2) | C14—C19 | 1.387 (6) |
N2—C6 | 1.399 (2) | C14—C15' | 1.394 (9) |
N2—H2N | 0.8824 | C14—C19' | 1.395 (5) |
N3—C12 | 1.450 (2) | C17—C16' | 1.335 (10) |
N3—C13 | 1.456 (2) | C17—C18' | 1.349 (11) |
N3—H3N | 0.9049 | C17—C18 | 1.369 (11) |
C1—C2 | 1.383 (2) | C17—C16 | 1.414 (11) |
C1—C6 | 1.399 (2) | C17—H17 | 0.9300 |
C2—C3 | 1.385 (2) | C15'—C16' | 1.373 (11) |
C2—H2 | 0.9300 | C15'—H15' | 0.9300 |
C3—C4 | 1.380 (3) | C16'—H16' | 0.9300 |
C3—H3 | 0.9300 | C18'—C19' | 1.387 (11) |
C4—C5 | 1.377 (3) | C18'—H18' | 0.9300 |
C4—H4 | 0.9300 | C19'—H19' | 0.9300 |
C5—C6 | 1.387 (2) | C15—C16 | 1.388 (12) |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
C7—C8 | 1.510 (2) | C16—H16 | 0.9300 |
C8—H8A | 0.9700 | C18—C19 | 1.391 (11) |
C8—H8B | 0.9700 | C18—H18 | 0.9300 |
C11—C12 | 1.509 (2) | C19—H19 | 0.9300 |
C12—H12A | 0.9700 | ||
C11—N1—C1 | 125.98 (12) | H12A—C12—H12B | 108.3 |
C11—N1—C8 | 118.09 (13) | N3—C13—C14 | 113.35 (13) |
C1—N1—C8 | 114.39 (12) | N3—C13—H13A | 108.9 |
C7—N2—C6 | 123.31 (14) | C14—C13—H13A | 108.9 |
C7—N2—H2N | 115.6 | N3—C13—H13B | 108.9 |
C6—N2—H2N | 121.0 | C14—C13—H13B | 108.9 |
C12—N3—C13 | 113.15 (13) | H13A—C13—H13B | 107.7 |
C12—N3—H3N | 107.7 | C15—C14—C19 | 121.0 (5) |
C13—N3—H3N | 112.2 | C15'—C14—C19' | 115.3 (4) |
C2—C1—C6 | 119.70 (14) | C15—C14—C13 | 118.9 (4) |
C2—C1—N1 | 124.13 (13) | C19—C14—C13 | 120.0 (3) |
C6—C1—N1 | 116.17 (13) | C15'—C14—C13 | 123.8 (4) |
C1—C2—C3 | 119.80 (15) | C19'—C14—C13 | 120.7 (3) |
C1—C2—H2 | 120.1 | C16'—C17—C18' | 121.5 (5) |
C3—C2—H2 | 120.1 | C18—C17—C16 | 117.6 (5) |
C4—C3—C2 | 120.51 (16) | C16'—C17—H17 | 118.1 |
C4—C3—H3 | 119.7 | C18'—C17—H17 | 120.4 |
C2—C3—H3 | 119.7 | C18—C17—H17 | 121.2 |
C5—C4—C3 | 119.98 (16) | C16—C17—H17 | 121.2 |
C5—C4—H4 | 120.0 | C16'—C15'—C14 | 123.0 (8) |
C3—C4—H4 | 120.0 | C16'—C15'—H15' | 118.5 |
C4—C5—C6 | 120.24 (16) | C14—C15'—H15' | 118.5 |
C4—C5—H5 | 119.9 | C17—C16'—C15' | 118.9 (8) |
C6—C5—H5 | 119.9 | C17—C16'—H16' | 120.6 |
C5—C6—C1 | 119.70 (15) | C15'—C16'—H16' | 120.6 |
C5—C6—N2 | 120.69 (14) | C17—C18'—C19' | 120.2 (6) |
C1—C6—N2 | 119.58 (14) | C17—C18'—H18' | 119.9 |
O1—C7—N2 | 122.90 (15) | C19'—C18'—H18' | 119.9 |
O1—C7—C8 | 122.08 (15) | C18'—C19'—C14 | 120.8 (6) |
N2—C7—C8 | 115.00 (14) | C18'—C19'—H19' | 119.6 |
N1—C8—C7 | 110.73 (13) | C14—C19'—H19' | 119.6 |
N1—C8—H8A | 109.5 | C14—C15—C16 | 119.7 (8) |
C7—C8—H8A | 109.5 | C14—C15—H15 | 120.1 |
N1—C8—H8B | 109.5 | C16—C15—H15 | 120.1 |
C7—C8—H8B | 109.5 | C15—C16—C17 | 120.9 (8) |
H8A—C8—H8B | 108.1 | C15—C16—H16 | 119.5 |
O11—C11—N1 | 119.82 (14) | C17—C16—H16 | 119.5 |
O11—C11—C12 | 120.36 (14) | C17—C18—C19 | 121.0 (7) |
N1—C11—C12 | 119.81 (13) | C17—C18—H18 | 119.5 |
N3—C12—C11 | 109.11 (12) | C19—C18—H18 | 119.5 |
N3—C12—H12A | 109.9 | C14—C19—C18 | 119.5 (6) |
C11—C12—H12A | 109.9 | C14—C19—H19 | 120.3 |
N3—C12—H12B | 109.9 | C18—C19—H19 | 120.3 |
C11—C12—H12B | 109.9 | ||
C11—N1—C1—C2 | −50.3 (2) | N3—C13—C14—C19' | 167.4 (6) |
C8—N1—C1—C2 | 144.16 (16) | C15—C14—C15'—C16' | −95.3 (18) |
C11—N1—C1—C6 | 130.61 (16) | C19—C14—C15'—C16' | 25.8 (8) |
C8—N1—C1—C6 | −34.89 (19) | C19'—C14—C15'—C16' | −6.4 (8) |
C6—C1—C2—C3 | −3.2 (2) | C13—C14—C15'—C16' | 179.0 (5) |
N1—C1—C2—C3 | 177.82 (15) | C18'—C17—C16'—C15' | −0.1 (9) |
C1—C2—C3—C4 | 1.9 (3) | C18—C17—C16'—C15' | −30.8 (8) |
C2—C3—C4—C5 | 0.3 (3) | C16—C17—C16'—C15' | 73.5 (13) |
C3—C4—C5—C6 | −1.2 (3) | C14—C15'—C16'—C17 | 4.3 (10) |
C4—C5—C6—C1 | −0.1 (3) | C16'—C17—C18'—C19' | −1.4 (10) |
C4—C5—C6—N2 | −178.06 (16) | C18—C17—C18'—C19' | 80.6 (13) |
C2—C1—C6—C5 | 2.2 (2) | C16—C17—C18'—C19' | −29.0 (9) |
N1—C1—C6—C5 | −178.66 (14) | C17—C18'—C19'—C14 | −1.1 (10) |
C2—C1—C6—N2 | −179.74 (14) | C15—C14—C19'—C18' | 30.8 (8) |
N1—C1—C6—N2 | −0.7 (2) | C19—C14—C19'—C18' | −82.6 (9) |
C7—N2—C6—C5 | −164.15 (16) | C15'—C14—C19'—C18' | 4.7 (8) |
C7—N2—C6—C1 | 17.9 (2) | C13—C14—C19'—C18' | 179.5 (5) |
C6—N2—C7—O1 | −179.41 (15) | C19—C14—C15—C16 | 4.4 (8) |
C6—N2—C7—C8 | 2.1 (2) | C15'—C14—C15—C16 | 73.9 (16) |
C11—N1—C8—C7 | −113.87 (16) | C19'—C14—C15—C16 | −28.0 (8) |
C1—N1—C8—C7 | 52.85 (19) | C13—C14—C15—C16 | −177.3 (5) |
O1—C7—C8—N1 | 145.30 (16) | C14—C15—C16—C17 | −2.7 (11) |
N2—C7—C8—N1 | −36.2 (2) | C16'—C17—C16—C15 | −87.1 (16) |
C1—N1—C11—O11 | −171.28 (15) | C18'—C17—C16—C15 | 31.7 (9) |
C8—N1—C11—O11 | −6.3 (2) | C18—C17—C16—C15 | 1.7 (10) |
C1—N1—C11—C12 | 9.4 (2) | C16'—C17—C18—C19 | 27.1 (9) |
C8—N1—C11—C12 | 174.44 (13) | C18'—C17—C18—C19 | −85.5 (13) |
C13—N3—C12—C11 | −163.52 (13) | C16—C17—C18—C19 | −2.4 (9) |
O11—C11—C12—N3 | 27.0 (2) | C15—C14—C19—C18 | −5.1 (8) |
N1—C11—C12—N3 | −153.67 (14) | C15'—C14—C19—C18 | −29.0 (7) |
C12—N3—C13—C14 | −73.1 (2) | C19'—C14—C19—C18 | 76.5 (9) |
N3—C13—C14—C15 | −45.8 (7) | C13—C14—C19—C18 | 176.7 (5) |
N3—C13—C14—C19 | 132.5 (6) | C17—C18—C19—C14 | 4.1 (10) |
N3—C13—C14—C15' | −18.3 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O1i | 0.88 | 2.00 | 2.879 (2) | 175 |
N3—H3N···O11 | 0.90 | 2.25 | 2.6804 (18) | 109 |
N3—H3N···O11ii | 0.90 | 2.36 | 3.056 (2) | 134 |
C2—H2···N3iii | 0.93 | 2.62 | 3.535 (2) | 169 |
C8—H8B···O11 | 0.97 | 2.23 | 2.682 (2) | 107 |
C17—H17···O1iv | 0.93 | 2.53 | 3.422 (3) | 161 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y+1, −z+1; (iii) x+1, y, z; (iv) x, y−1, z. |
Torsion angle | (II) | (IIB) |
C8—N1—C11—C12 | 174.44 (13) | 166.0 (5) |
N1—C11—C12—N3 | -153.67 (14) | -145.6 (5) |
C11—C12—N3—C13 | -163.52 (13) | 65.3 (6) |
C12—N3—C13—C14 | -73.1 (2) | 176.3 (4) |
N3—C13—C14—C15 | -45.8 (7) | -12.9 (8) |
N3—C13—C14—C15" | -18.3 (6) | – |