Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807010562/lh2313sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807010562/lh2313Isup2.hkl |
CCDC reference: 647260
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Version 1.4; Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).
C21H24N2O3 | F(000) = 752 |
Mr = 352.42 | Dx = 1.206 Mg m−3 |
Monoclinic, P21/n | Melting point: 389 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8917 (4) Å | Cell parameters from 22 reflections |
b = 12.9205 (9) Å | θ = 8.2–11.6° |
c = 15.5882 (9) Å | µ = 0.08 mm−1 |
β = 103.216 (6)° | T = 290 K |
V = 1939.5 (2) Å3 | Prism, colourless |
Z = 4 | 0.5 × 0.25 × 0.1 mm |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.035 |
Radiation source: fine-focus sealed tube | θmax = 26.0°, θmin = 2.1° |
Graphite monochromator | h = −12→11 |
Non–profiled ω/2θ scans | k = 0→15 |
3907 measured reflections | l = 0→19 |
3770 independent reflections | 3 standard reflections every 200 reflections |
2371 reflections with I > 2σ(I) | intensity decay: −1% |
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)] = 0.089 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.292 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.1806P)2 + 0.5652P] where P = (Fo2 + 2Fc2)/3 |
3770 reflections | (Δ/σ)max < 0.001 |
236 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
Experimental. The 1H NMR spectrum of (I) was obtained on a Bruker Advance DRX-250 spectrometer at 250.13 MHz in DMSOd6 at 293 K with tetramethylsilane as internal standard. 1H NMR (250 MHz, DMSOd6, p.p.m.): 0.81–0.92 (3H, m, –CH3), 1.18–1.35 (6H, m, –CH2–), 1.45–1.63 (2H, m, –CH2–), 2.73–2.84 (1H, m, –CH2–), 4.03–4.15 (1H, m, –CH2–), 4.41 (1H, d, J = 1.0 Hz, H8), 5.33 (1H, d, J = 1.0 Hz, H9), 7.01 (1H, dd, J = 7.9 Hz, Ph—H), 7.17–7.21 (2H, m, Ph—H), 7.30–7.39 (2H, m, Pyr-H), 7.66 (1H, dt, J = 1.8 and 7.8 Hz, Ph—H), 7.87 (1H, dd, J = 2.3 and 6.8 Hz, Ph—H), 8.48 (1H, dm, J = 4.8 Hz, Pyr-H). |
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 | ||
O1 | 0.5371 (2) | 0.32470 (19) | 0.75690 (19) | 0.0754 (8) | |
H1 | 0.5690 | 0.2580 | 0.7450 | 0.113* | |
O2 | 0.9082 (2) | 0.63213 (18) | 0.77527 (18) | 0.0671 (7) | |
O3 | 0.7486 (3) | 0.3350 (2) | 0.8398 (2) | 0.0922 (11) | |
N1 | 0.6857 (3) | 0.5773 (2) | 0.73663 (18) | 0.0525 (7) | |
N2 | 0.3546 (3) | 0.6176 (3) | 0.8012 (2) | 0.0724 (9) | |
C1 | 0.8024 (3) | 0.6005 (2) | 0.7976 (2) | 0.0518 (8) | |
C2 | 0.8010 (3) | 0.5845 (2) | 0.8909 (2) | 0.0507 (8) | |
C3 | 0.9065 (4) | 0.6258 (3) | 0.9571 (3) | 0.0648 (10) | |
H3 | 0.9749 | 0.6668 | 0.9421 | 0.078* | |
C4 | 0.9102 (4) | 0.6065 (3) | 1.0438 (3) | 0.0767 (12) | |
H4 | 0.9805 | 0.6348 | 1.0875 | 0.092* | |
C5 | 0.8093 (4) | 0.5446 (3) | 1.0666 (3) | 0.0755 (11) | |
H5 | 0.8125 | 0.5313 | 1.1256 | 0.091* | |
C6 | 0.7053 (4) | 0.5031 (3) | 1.0027 (2) | 0.0639 (9) | |
H6 | 0.6382 | 0.4615 | 1.0185 | 0.077* | |
C7 | 0.6993 (3) | 0.5228 (2) | 0.9143 (2) | 0.0507 (8) | |
C8 | 0.5907 (3) | 0.4758 (2) | 0.8417 (2) | 0.0510 (8) | |
H8 | 0.5059 | 0.4662 | 0.8633 | 0.061* | |
C9 | 0.5578 (3) | 0.5491 (2) | 0.7628 (2) | 0.0513 (8) | |
H9 | 0.5001 | 0.5106 | 0.7136 | 0.062* | |
C10 | 0.4735 (3) | 0.6428 (3) | 0.7799 (2) | 0.0537 (8) | |
C11 | 0.2733 (4) | 0.6959 (4) | 0.8148 (3) | 0.0884 (14) | |
H11 | 0.1908 | 0.6800 | 0.8309 | 0.106* | |
C12 | 0.3050 (4) | 0.7987 (4) | 0.8062 (3) | 0.0827 (13) | |
H12 | 0.2448 | 0.8505 | 0.8156 | 0.099* | |
C13 | 0.4258 (4) | 0.8227 (3) | 0.7837 (3) | 0.0710 (10) | |
H13 | 0.4501 | 0.8915 | 0.7782 | 0.085* | |
C14 | 0.5132 (3) | 0.7436 (3) | 0.7688 (2) | 0.0614 (9) | |
H14 | 0.5955 | 0.7580 | 0.7519 | 0.074* | |
C15 | 0.6356 (3) | 0.3708 (2) | 0.8141 (2) | 0.0541 (8) | |
C16 | 0.6813 (4) | 0.5874 (3) | 0.6430 (2) | 0.0612 (9) | |
H16A | 0.7462 | 0.6408 | 0.6350 | 0.073* | |
H16B | 0.5890 | 0.6096 | 0.6127 | 0.073* | |
C17 | 0.7161 (4) | 0.4887 (3) | 0.6013 (3) | 0.0732 (11) | |
H17A | 0.6496 | 0.4357 | 0.6077 | 0.088* | |
H17B | 0.8074 | 0.4654 | 0.6325 | 0.088* | |
C18 | 0.7151 (5) | 0.5006 (4) | 0.5049 (3) | 0.0907 (14) | |
H18A | 0.7821 | 0.5535 | 0.4992 | 0.109* | |
H18B | 0.6242 | 0.5254 | 0.4746 | 0.109* | |
C19 | 0.7477 (7) | 0.4033 (6) | 0.4583 (4) | 0.125 (2) | |
H19A | 0.6821 | 0.3500 | 0.4655 | 0.150* | |
H19B | 0.7318 | 0.4182 | 0.3959 | 0.150* | |
C20 | 0.8796 (8) | 0.3637 (6) | 0.4859 (6) | 0.152 (3) | |
H20A | 0.8880 | 0.3390 | 0.5456 | 0.182* | |
H20B | 0.9433 | 0.4214 | 0.4894 | 0.182* | |
C21 | 0.9324 (7) | 0.2802 (5) | 0.4374 (5) | 0.145 (3) | |
H21A | 1.0229 | 0.2593 | 0.4697 | 0.217* | |
H21B | 0.9383 | 0.3050 | 0.3803 | 0.217* | |
H21C | 0.8704 | 0.2221 | 0.4307 | 0.217* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0511 (14) | 0.0528 (14) | 0.116 (2) | −0.0002 (11) | 0.0064 (13) | −0.0203 (14) |
O2 | 0.0424 (12) | 0.0561 (14) | 0.107 (2) | 0.0028 (10) | 0.0272 (12) | 0.0200 (13) |
O3 | 0.0488 (15) | 0.0600 (16) | 0.156 (3) | 0.0105 (12) | −0.0001 (16) | −0.0304 (17) |
N1 | 0.0429 (14) | 0.0500 (15) | 0.0673 (18) | 0.0035 (11) | 0.0182 (12) | 0.0040 (12) |
N2 | 0.0455 (15) | 0.070 (2) | 0.107 (2) | 0.0130 (14) | 0.0296 (16) | 0.0178 (17) |
C1 | 0.0425 (16) | 0.0380 (15) | 0.076 (2) | 0.0063 (12) | 0.0157 (15) | 0.0073 (14) |
C2 | 0.0433 (16) | 0.0392 (15) | 0.069 (2) | 0.0070 (12) | 0.0122 (14) | −0.0014 (14) |
C3 | 0.0492 (18) | 0.0500 (19) | 0.091 (3) | −0.0005 (15) | 0.0075 (18) | −0.0072 (18) |
C4 | 0.066 (2) | 0.071 (2) | 0.082 (3) | 0.005 (2) | −0.007 (2) | −0.017 (2) |
C5 | 0.077 (3) | 0.078 (3) | 0.070 (2) | 0.007 (2) | 0.013 (2) | −0.008 (2) |
C6 | 0.060 (2) | 0.061 (2) | 0.071 (2) | 0.0043 (17) | 0.0159 (17) | 0.0045 (18) |
C7 | 0.0441 (16) | 0.0395 (15) | 0.069 (2) | 0.0081 (13) | 0.0133 (14) | −0.0011 (14) |
C8 | 0.0396 (15) | 0.0436 (16) | 0.073 (2) | 0.0007 (12) | 0.0202 (14) | −0.0002 (15) |
C9 | 0.0394 (15) | 0.0472 (17) | 0.068 (2) | 0.0010 (13) | 0.0133 (14) | −0.0005 (15) |
C10 | 0.0397 (15) | 0.0515 (18) | 0.068 (2) | 0.0064 (13) | 0.0096 (14) | 0.0069 (15) |
C11 | 0.053 (2) | 0.092 (3) | 0.129 (4) | 0.024 (2) | 0.040 (2) | 0.021 (3) |
C12 | 0.062 (2) | 0.076 (3) | 0.110 (3) | 0.029 (2) | 0.020 (2) | 0.003 (2) |
C13 | 0.065 (2) | 0.054 (2) | 0.089 (3) | 0.0152 (17) | 0.0065 (19) | 0.0004 (18) |
C14 | 0.0455 (17) | 0.0538 (19) | 0.084 (2) | 0.0050 (14) | 0.0128 (16) | 0.0029 (17) |
C15 | 0.0397 (16) | 0.0412 (16) | 0.083 (2) | −0.0043 (13) | 0.0165 (15) | −0.0022 (15) |
C16 | 0.0565 (19) | 0.055 (2) | 0.075 (2) | 0.0021 (16) | 0.0205 (17) | 0.0030 (17) |
C17 | 0.074 (2) | 0.066 (2) | 0.082 (3) | 0.0041 (19) | 0.025 (2) | −0.0049 (19) |
C18 | 0.082 (3) | 0.100 (4) | 0.093 (3) | 0.011 (3) | 0.026 (2) | −0.014 (3) |
C19 | 0.106 (4) | 0.158 (6) | 0.116 (4) | 0.012 (4) | 0.035 (4) | −0.027 (4) |
C20 | 0.130 (6) | 0.134 (6) | 0.176 (7) | 0.035 (5) | 0.002 (5) | −0.039 (5) |
C21 | 0.137 (6) | 0.128 (5) | 0.183 (7) | 0.008 (4) | 0.065 (5) | −0.058 (5) |
O1—C15 | 1.305 (4) | C10—C14 | 1.382 (5) |
O1—H1 | 0.9502 | C11—C12 | 1.379 (6) |
O2—C1 | 1.245 (4) | C11—H11 | 0.9300 |
O3—C15 | 1.191 (4) | C12—C13 | 1.356 (6) |
N1—C1 | 1.351 (4) | C12—H12 | 0.9300 |
N1—C16 | 1.456 (4) | C13—C14 | 1.392 (5) |
N1—C9 | 1.461 (4) | C13—H13 | 0.9300 |
N2—C10 | 1.334 (4) | C14—H14 | 0.9300 |
N2—C11 | 1.339 (5) | C16—C17 | 1.507 (5) |
C1—C2 | 1.472 (5) | C16—H16A | 0.9700 |
C2—C3 | 1.395 (5) | C16—H16B | 0.9700 |
C2—C7 | 1.396 (4) | C17—C18 | 1.507 (6) |
C3—C4 | 1.366 (6) | C17—H17A | 0.9700 |
C3—H3 | 0.9300 | C17—H17B | 0.9700 |
C4—C5 | 1.387 (6) | C18—C19 | 1.523 (7) |
C4—H4 | 0.9300 | C18—H18A | 0.9700 |
C5—C6 | 1.367 (5) | C18—H18B | 0.9700 |
C5—H5 | 0.9300 | C19—C20 | 1.376 (8) |
C6—C7 | 1.389 (5) | C19—H19A | 0.9700 |
C6—H6 | 0.9300 | C19—H19B | 0.9700 |
C7—C8 | 1.500 (5) | C20—C21 | 1.479 (8) |
C8—C15 | 1.519 (4) | C20—H20A | 0.9700 |
C8—C9 | 1.527 (5) | C20—H20B | 0.9700 |
C8—H8 | 0.9800 | C21—H21A | 0.9600 |
C9—C10 | 1.529 (4) | C21—H21B | 0.9600 |
C9—H9 | 0.9800 | C21—H21C | 0.9600 |
C15—O1—H1 | 108.6 | C11—C12—H12 | 120.7 |
C1—N1—C16 | 120.7 (3) | C12—C13—C14 | 119.5 (4) |
C1—N1—C9 | 120.9 (3) | C12—C13—H13 | 120.2 |
C16—N1—C9 | 118.2 (3) | C14—C13—H13 | 120.2 |
C10—N2—C11 | 116.8 (3) | C10—C14—C13 | 117.8 (3) |
O2—C1—N1 | 120.9 (3) | C10—C14—H14 | 121.1 |
O2—C1—C2 | 121.4 (3) | C13—C14—H14 | 121.1 |
N1—C1—C2 | 117.7 (3) | O3—C15—O1 | 123.3 (3) |
C3—C2—C7 | 119.1 (3) | O3—C15—C8 | 124.4 (3) |
C3—C2—C1 | 120.2 (3) | O1—C15—C8 | 112.3 (3) |
C7—C2—C1 | 120.6 (3) | N1—C16—C17 | 113.5 (3) |
C4—C3—C2 | 120.5 (4) | N1—C16—H16A | 108.9 |
C4—C3—H3 | 119.7 | C17—C16—H16A | 108.9 |
C2—C3—H3 | 119.7 | N1—C16—H16B | 108.9 |
C3—C4—C5 | 120.0 (4) | C17—C16—H16B | 108.9 |
C3—C4—H4 | 120.0 | H16A—C16—H16B | 107.7 |
C5—C4—H4 | 120.0 | C16—C17—C18 | 113.1 (3) |
C6—C5—C4 | 120.4 (4) | C16—C17—H17A | 109.0 |
C6—C5—H5 | 119.8 | C18—C17—H17A | 109.0 |
C4—C5—H5 | 119.8 | C16—C17—H17B | 109.0 |
C5—C6—C7 | 120.3 (4) | C18—C17—H17B | 109.0 |
C5—C6—H6 | 119.8 | H17A—C17—H17B | 107.8 |
C7—C6—H6 | 119.8 | C17—C18—C19 | 115.9 (5) |
C6—C7—C2 | 119.6 (3) | C17—C18—H18A | 108.3 |
C6—C7—C8 | 122.4 (3) | C19—C18—H18A | 108.3 |
C2—C7—C8 | 117.9 (3) | C17—C18—H18B | 108.3 |
C7—C8—C15 | 111.7 (2) | C19—C18—H18B | 108.3 |
C7—C8—C9 | 109.9 (3) | H18A—C18—H18B | 107.4 |
C15—C8—C9 | 110.3 (3) | C20—C19—C18 | 116.6 (6) |
C7—C8—H8 | 108.3 | C20—C19—H19A | 108.1 |
C15—C8—H8 | 108.3 | C18—C19—H19A | 108.1 |
C9—C8—H8 | 108.3 | C20—C19—H19B | 108.1 |
N1—C9—C8 | 110.0 (2) | C18—C19—H19B | 108.1 |
N1—C9—C10 | 113.1 (3) | H19A—C19—H19B | 107.3 |
C8—C9—C10 | 112.0 (3) | C19—C20—C21 | 122.2 (7) |
N1—C9—H9 | 107.1 | C19—C20—H20A | 106.8 |
C8—C9—H9 | 107.1 | C21—C20—H20A | 106.8 |
C10—C9—H9 | 107.1 | C19—C20—H20B | 106.8 |
N2—C10—C14 | 123.6 (3) | C21—C20—H20B | 106.8 |
N2—C10—C9 | 113.4 (3) | H20A—C20—H20B | 106.6 |
C14—C10—C9 | 122.9 (3) | C20—C21—H21A | 109.5 |
N2—C11—C12 | 123.7 (4) | C20—C21—H21B | 109.5 |
N2—C11—H11 | 118.2 | H21A—C21—H21B | 109.5 |
C12—C11—H11 | 118.2 | C20—C21—H21C | 109.5 |
C13—C12—C11 | 118.6 (4) | H21A—C21—H21C | 109.5 |
C13—C12—H12 | 120.7 | H21B—C21—H21C | 109.5 |
C9—N1—C1—O2 | −174.5 (3) | C10—N2—C11—H11 | −178.7 |
C9—N1—C1—C2 | 7.1 (4) | C1—C2—C3—H3 | 3.6 |
C16—N1—C1—O2 | 0.7 (4) | C7—C2—C3—H3 | 179.8 |
C16—N1—C1—C2 | −177.6 (3) | C2—C3—C4—H4 | −179.4 |
C1—N1—C9—C8 | −42.5 (4) | H3—C3—C4—C5 | −179.4 |
C1—N1—C9—C10 | 83.5 (3) | H3—C3—C4—H4 | 0.6 |
C16—N1—C9—C8 | 142.1 (3) | C3—C4—C5—H5 | 179.6 |
C16—N1—C9—C10 | −91.8 (3) | H4—C4—C5—C6 | 179.6 |
C1—N1—C16—C17 | 93.3 (4) | H4—C4—C5—H5 | −0.4 |
C9—N1—C16—C17 | −91.3 (4) | C4—C5—C6—H6 | 179.8 |
C11—N2—C10—C9 | −178.2 (3) | H5—C5—C6—C7 | 179.8 |
C11—N2—C10—C14 | −2.2 (6) | H5—C5—C6—H6 | −0.2 |
C10—N2—C11—C12 | 1.3 (7) | H6—C6—C7—C2 | −179.4 |
O2—C1—C2—C3 | 14.4 (4) | H6—C6—C7—C8 | −2.5 |
O2—C1—C2—C7 | −161.6 (3) | C2—C7—C8—H8 | −151.8 |
N1—C1—C2—C3 | −167.2 (3) | C6—C7—C8—H8 | 31.3 |
N1—C1—C2—C7 | 16.7 (4) | C7—C8—C9—H9 | 169.8 |
C1—C2—C3—C4 | −176.4 (3) | C15—C8—C9—H9 | 46.2 |
C7—C2—C3—C4 | −0.2 (5) | H8—C8—C9—N1 | 171.8 |
C1—C2—C7—C6 | 175.8 (3) | H8—C8—C9—C10 | 45.1 |
C1—C2—C7—C8 | −1.3 (4) | H8—C8—C9—H9 | −72.1 |
C3—C2—C7—C6 | −0.4 (4) | H8—C8—C15—O1 | 54.8 |
C3—C2—C7—C8 | −177.4 (3) | H8—C8—C15—O3 | −126.7 |
C2—C3—C4—C5 | 0.6 (6) | H9—C9—C10—N2 | 60.2 |
C3—C4—C5—C6 | −0.4 (6) | H9—C9—C10—C14 | −115.9 |
C4—C5—C6—C7 | −0.2 (6) | N2—C10—C14—H14 | −177.7 |
C5—C6—C7—C2 | 0.6 (5) | C9—C10—C14—H14 | −2.0 |
C5—C6—C7—C8 | 177.5 (3) | N2—C11—C12—H12 | 179.3 |
C2—C7—C8—C9 | −33.7 (4) | H11—C11—C12—C13 | 179.3 |
C2—C7—C8—C15 | 89.1 (3) | H11—C11—C12—H12 | −0.7 |
C6—C7—C8—C9 | 149.3 (3) | C11—C12—C13—H13 | −179.2 |
C6—C7—C8—C15 | −87.9 (4) | H12—C12—C13—C14 | −179.2 |
C7—C8—C9—N1 | 53.7 (3) | H12—C12—C13—H13 | 0.8 |
C7—C8—C9—C10 | −73.0 (3) | C12—C13—C14—H14 | 178.4 |
C15—C8—C9—N1 | −69.9 (3) | H13—C13—C14—C10 | 178.4 |
C15—C8—C9—C10 | 163.4 (2) | H13—C13—C14—H14 | −1.6 |
C7—C8—C15—O1 | 174.0 (3) | N1—C16—C17—H17A | 60.2 |
C7—C8—C15—O3 | −7.6 (5) | N1—C16—C17—H17B | −57.1 |
C9—C8—C15—O1 | −63.5 (4) | H16A—C16—C17—C18 | −57.0 |
C9—C8—C15—O3 | 114.9 (4) | H16A—C16—C17—H17A | −178.4 |
N1—C9—C10—N2 | 178.1 (3) | H16A—C16—C17—H17B | 64.3 |
N1—C9—C10—C14 | 2.0 (5) | H16B—C16—C17—C18 | 60.1 |
C8—C9—C10—N2 | −57.0 (4) | H16B—C16—C17—H17A | −61.2 |
C8—C9—C10—C14 | 126.9 (3) | H16B—C16—C17—H17B | −178.5 |
N2—C10—C14—C13 | 2.3 (6) | C16—C17—C18—H18A | 58.8 |
C9—C10—C14—C13 | 178.0 (3) | C16—C17—C18—H18B | −57.4 |
N2—C11—C12—C13 | −0.7 (8) | H17A—C17—C18—C19 | −57.9 |
C11—C12—C13—C14 | 0.8 (7) | H17A—C17—C18—H18A | −179.8 |
C12—C13—C14—C10 | −1.6 (6) | H17A—C17—C18—H18B | 64.0 |
N1—C16—C17—C18 | −178.4 (3) | H17B—C17—C18—C19 | 59.4 |
C16—C17—C18—C19 | −179.3 (4) | H17B—C17—C18—H18A | −62.5 |
C17—C18—C19—C20 | −65.4 (8) | H17B—C17—C18—H18B | −178.7 |
C18—C19—C20—C21 | −169.9 (7) | C17—C18—C19—H19A | 56.6 |
H1—O1—C15—O3 | 5.2 | C17—C18—C19—H19B | 172.5 |
H1—O1—C15—C8 | −176.4 | H18A—C18—C19—C20 | 56.4 |
C1—N1—C9—H9 | −158.6 | H18A—C18—C19—H19A | 178.5 |
C16—N1—C9—H9 | 26.0 | H18A—C18—C19—H19B | −65.6 |
C1—N1—C16—H16A | −28.1 | H18B—C18—C19—C20 | 172.7 |
C1—N1—C16—H16B | −145.3 | H18B—C18—C19—H19A | −65.3 |
C9—N1—C16—H16A | 147.3 | H18B—C18—C19—H19B | 50.6 |
C9—N1—C16—H16B | 30.1 | C18—C19—C20—H20A | 66.9 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.95 | 1.68 | 2.619 (2) | 168 |
C4—H4···O3ii | 0.93 | 2.69 | 3.529 (3) | 151 |
C14—H14···O3iii | 0.93 | 2.53 | 3.411 (3) | 157 |
C16—H16A···O3iii | 0.97 | 2.54 | 3.271 (3) | 132 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+2, −y+1, −z+2; (iii) −x+3/2, y+1/2, −z+3/2. |