Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109022203/gg3195sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109022203/gg3195Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109022203/gg3195IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109022203/gg3195IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109022203/gg3195IVsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109022203/gg3195Vsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109022203/gg3195VIsup7.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108270109022203/gg3195sup8.pdf |
CCDC references: 746064; 746065; 746066; 746067; 746068; 746069
Benzil (1 mmol), the appropriate benzaldehyde (1 mmol) and ammonium acetate (1.2 g) were dissolved in boiling glacial acetic acid (16 ml) and refluxed for 5–24 h. On completion of the reaction, the reaction mixture was poured into ice water, washed with NaHCO3 and then washed several times with EtOAc. The combined extracts were dried over MgSO4. The purification was done by flash column chromatography. Compound (I) crystallizes from ethanol as light yellow plates, in the monoclinic space group Cc (Fig. 1) and from acetonitrile as light yellow plates to form the solvatee (II) in the orthorhombic space group Pbca (Fig. 2). Compound (III) crystallizes from methanol as the solvate in light yellow plates in the monoclinic space group P21/c with Z' = 2 (Figs. 3a,b). Compound (IV) crystallizes from methanol as light yellow solvate plates (Fig. 4), (V) from acetonitrile as light yellow plates, both in the monoclinic space group P21/c (Fig. 5). Compound (VI) crystallizes from ethanol as light yellow prisms in the triclinic space group P1 with Z' = 2 for (III) (Figs. 6a,b).
H atoms were clearly found in the difference Fourier maps. The amine H atom was refined at the earlier stages of the refinement and was fixed at the later stages. All other H atoms were refined at idealized positions riding on the C and N atoms with C—H = 0.96 Å, N—H = 0.86 Å and O—H = 0.82 Å; Uiso(H) = 1.2Ueq(C N or O).
For all compounds, data collection: COLLECT (Nonius, 2000). Cell refinement: DENZO HKL-2000 (Otwinowski & Minor ,1997) for (I); DENZO HKL-2000 (Otwinowski & Minor, 1997) for (II), (III), (IV), (V), (VI). Data reduction: DENZO HKL-2000 (Otwinowski & Minor, 1997) for (I), (III), (IV), (V), (VI); DENZO HKL-2000 (Otwinowski & Minor ,1997) for (II). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999).
C21H15N3O2 | F(000) = 712 |
Mr = 341.36 | Dx = 1.294 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 6192 reflections |
a = 10.521 (2) Å | θ = 2.1–25.0° |
b = 19.769 (4) Å | µ = 0.09 mm−1 |
c = 9.056 (2) Å | T = 293 K |
β = 111.49 (3)° | Plate, yellow |
V = 1752.6 (7) Å3 | 0.59 × 0.37 × 0.08 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 943 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.083 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ϕ– and ω–scans | h = 0→12 |
6192 measured reflections | k = 0→23 |
1533 independent reflections | l = −10→10 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.043P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.090 | (Δ/σ)max < 0.001 |
S = 0.88 | Δρmax = 0.12 e Å−3 |
1533 reflections | Δρmin = −0.13 e Å−3 |
236 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0063 (10) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0 (10) |
C21H15N3O2 | V = 1752.6 (7) Å3 |
Mr = 341.36 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 10.521 (2) Å | µ = 0.09 mm−1 |
b = 19.769 (4) Å | T = 293 K |
c = 9.056 (2) Å | 0.59 × 0.37 × 0.08 mm |
β = 111.49 (3)° |
Nonius KappaCCD diffractometer | 943 reflections with I > 2σ(I) |
6192 measured reflections | Rint = 0.083 |
1533 independent reflections |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.090 | Δρmax = 0.12 e Å−3 |
S = 0.88 | Δρmin = −0.13 e Å−3 |
1533 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
236 parameters | Absolute structure parameter: 0 (10) |
2 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.0133 (4) | 0.07649 (19) | 0.5894 (5) | 0.0882 (11) | |
O2 | 1.0818 (5) | 0.0473 (2) | 0.4015 (5) | 0.1215 (17) | |
N1 | 0.6824 (3) | 0.01307 (16) | 0.6075 (3) | 0.0458 (9) | |
H1 | 0.6894 | −0.0147 | 0.6832 | 0.055* | |
N2 | 0.7172 (3) | 0.05953 (16) | 0.4034 (3) | 0.0441 (9) | |
N3 | 1.0259 (5) | 0.0362 (3) | 0.4955 (5) | 0.0779 (13) | |
C1 | 0.8504 (4) | −0.0436 (2) | 0.5167 (4) | 0.0476 (12) | |
C2 | 0.8143 (5) | −0.1106 (3) | 0.5325 (5) | 0.0632 (14) | |
H2 | 0.7300 | −0.1190 | 0.5477 | 0.076* | |
C3 | 0.8998 (8) | −0.1628 (3) | 0.5278 (7) | 0.093 (2) | |
H3 | 0.8745 | −0.2085 | 0.5397 | 0.111* | |
C4 | 1.0185 (8) | −0.1499 (4) | 0.5053 (8) | 0.098 (2) | |
H4 | 1.0745 | −0.1876 | 0.5009 | 0.117* | |
C5 | 1.0567 (6) | −0.0851 (4) | 0.4913 (6) | 0.0832 (17) | |
H5 | 1.1394 | −0.0753 | 0.4738 | 0.100* | |
C6 | 0.9739 (5) | −0.0324 (3) | 0.4997 (5) | 0.0589 (13) | |
C7 | 0.7540 (4) | 0.0099 (2) | 0.5090 (4) | 0.0439 (10) | |
C8 | 0.5973 (4) | 0.0680 (2) | 0.5649 (4) | 0.0422 (10) | |
C9 | 0.6182 (4) | 0.09628 (18) | 0.4374 (4) | 0.0426 (10) | |
C10 | 0.5523 (5) | 0.1545 (2) | 0.3382 (4) | 0.0474 (11) | |
C11 | 0.6255 (5) | 0.1963 (2) | 0.2735 (5) | 0.0608 (13) | |
H11 | 0.7188 | 0.1785 | 0.3065 | 0.073* | |
C12 | 0.5661 (6) | 0.2520 (3) | 0.1820 (5) | 0.0750 (16) | |
H12 | 0.6185 | 0.2804 | 0.1395 | 0.090* | |
C13 | 0.4324 (7) | 0.2668 (3) | 0.1529 (6) | 0.0815 (17) | |
H13 | 0.3909 | 0.3055 | 0.0897 | 0.098* | |
C14 | 0.3564 (6) | 0.2266 (3) | 0.2127 (6) | 0.0805 (16) | |
H14 | 0.2618 | 0.2367 | 0.1895 | 0.097* | |
C15 | 0.4170 (5) | 0.1701 (3) | 0.3060 (5) | 0.0637 (13) | |
H15 | 0.3624 | 0.1431 | 0.3481 | 0.076* | |
C16 | 0.5125 (4) | 0.0873 (2) | 0.6572 (4) | 0.0466 (11) | |
C17 | 0.5084 (4) | 0.1539 (2) | 0.7027 (5) | 0.0576 (12) | |
H17 | 0.5577 | 0.1880 | 0.6704 | 0.069* | |
C18 | 0.4345 (6) | 0.1718 (3) | 0.7930 (6) | 0.0748 (15) | |
H18 | 0.4305 | 0.2183 | 0.8219 | 0.090* | |
C19 | 0.3669 (6) | 0.1234 (4) | 0.8429 (6) | 0.0861 (19) | |
H19 | 0.3159 | 0.1355 | 0.9078 | 0.103* | |
C20 | 0.3687 (5) | 0.0577 (3) | 0.7994 (6) | 0.0757 (16) | |
H20 | 0.3196 | 0.0242 | 0.8341 | 0.091* | |
C21 | 0.4417 (5) | 0.0395 (2) | 0.7067 (5) | 0.0578 (12) | |
H21 | 0.4434 | −0.0070 | 0.6763 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.080 (3) | 0.079 (3) | 0.108 (3) | −0.006 (2) | 0.035 (2) | −0.014 (2) |
O2 | 0.117 (4) | 0.157 (5) | 0.115 (3) | −0.027 (3) | 0.071 (3) | 0.004 (3) |
N1 | 0.058 (2) | 0.045 (2) | 0.0388 (18) | 0.0096 (19) | 0.0235 (18) | 0.0066 (15) |
N2 | 0.050 (2) | 0.043 (2) | 0.0427 (19) | 0.0058 (18) | 0.0218 (16) | 0.0010 (16) |
N3 | 0.066 (3) | 0.096 (4) | 0.075 (3) | 0.002 (3) | 0.029 (3) | −0.005 (3) |
C1 | 0.056 (3) | 0.050 (3) | 0.040 (2) | 0.021 (2) | 0.021 (2) | 0.0048 (19) |
C2 | 0.083 (4) | 0.054 (3) | 0.061 (3) | 0.014 (3) | 0.035 (3) | 0.001 (2) |
C3 | 0.131 (6) | 0.055 (4) | 0.089 (4) | 0.038 (4) | 0.038 (4) | 0.005 (3) |
C4 | 0.100 (5) | 0.090 (5) | 0.103 (4) | 0.054 (4) | 0.036 (4) | −0.007 (4) |
C5 | 0.072 (4) | 0.106 (5) | 0.076 (4) | 0.029 (4) | 0.032 (3) | −0.006 (3) |
C6 | 0.058 (3) | 0.073 (4) | 0.048 (3) | 0.015 (3) | 0.021 (2) | −0.003 (2) |
C7 | 0.051 (3) | 0.048 (3) | 0.037 (2) | 0.004 (2) | 0.021 (2) | −0.0007 (19) |
C8 | 0.047 (3) | 0.042 (3) | 0.040 (2) | 0.000 (2) | 0.0196 (19) | 0.0005 (19) |
C9 | 0.053 (3) | 0.037 (2) | 0.041 (2) | 0.006 (2) | 0.022 (2) | −0.0050 (18) |
C10 | 0.050 (3) | 0.045 (3) | 0.044 (2) | 0.004 (2) | 0.013 (2) | −0.0037 (19) |
C11 | 0.077 (4) | 0.053 (3) | 0.047 (2) | 0.005 (3) | 0.017 (2) | 0.003 (2) |
C12 | 0.098 (5) | 0.060 (4) | 0.055 (3) | −0.001 (3) | 0.014 (3) | 0.010 (2) |
C13 | 0.092 (5) | 0.055 (4) | 0.070 (3) | 0.008 (3) | −0.002 (3) | 0.005 (3) |
C14 | 0.071 (4) | 0.075 (5) | 0.075 (3) | 0.023 (3) | 0.002 (3) | −0.013 (3) |
C15 | 0.058 (3) | 0.063 (4) | 0.062 (3) | 0.007 (3) | 0.014 (2) | −0.009 (2) |
C16 | 0.049 (3) | 0.047 (3) | 0.048 (2) | 0.005 (2) | 0.023 (2) | −0.001 (2) |
C17 | 0.061 (3) | 0.063 (3) | 0.059 (3) | 0.006 (3) | 0.035 (2) | −0.008 (2) |
C18 | 0.092 (4) | 0.067 (4) | 0.078 (3) | 0.008 (3) | 0.047 (3) | −0.018 (3) |
C19 | 0.087 (5) | 0.111 (5) | 0.082 (4) | 0.033 (4) | 0.058 (4) | 0.010 (4) |
C20 | 0.072 (4) | 0.089 (5) | 0.079 (3) | 0.005 (3) | 0.043 (3) | 0.016 (3) |
C21 | 0.061 (3) | 0.062 (3) | 0.060 (3) | 0.007 (3) | 0.034 (3) | 0.005 (2) |
O1—N3 | 1.207 (5) | C10—C15 | 1.379 (6) |
O2—N3 | 1.219 (5) | C10—C11 | 1.396 (6) |
N1—C7 | 1.364 (4) | C11—C12 | 1.383 (6) |
N1—C8 | 1.370 (5) | C11—H11 | 0.9793 |
N1—H1 | 0.8600 | C12—C13 | 1.364 (7) |
N2—C7 | 1.324 (5) | C12—H12 | 0.9600 |
N2—C9 | 1.394 (5) | C13—C14 | 1.371 (7) |
N3—C6 | 1.469 (6) | C13—H13 | 0.9599 |
C1—C6 | 1.382 (6) | C14—C15 | 1.405 (7) |
C1—C2 | 1.400 (6) | C14—H14 | 0.9600 |
C1—C7 | 1.449 (6) | C15—H15 | 0.9600 |
C2—C3 | 1.380 (7) | C16—C21 | 1.375 (6) |
C2—H2 | 0.9600 | C16—C17 | 1.386 (5) |
C3—C4 | 1.361 (8) | C17—C18 | 1.366 (6) |
C3—H3 | 0.9584 | C17—H17 | 0.9600 |
C4—C5 | 1.363 (8) | C18—C19 | 1.365 (7) |
C4—H4 | 0.9600 | C18—H18 | 0.9600 |
C5—C6 | 1.377 (7) | C19—C20 | 1.360 (8) |
C5—H5 | 0.9600 | C19—H19 | 0.9600 |
C8—C9 | 1.371 (5) | C20—C21 | 1.378 (6) |
C8—C16 | 1.478 (5) | C20—H20 | 0.9600 |
C9—C10 | 1.469 (5) | C21—H21 | 0.9600 |
C7—N1—C8 | 108.2 (3) | C15—C10—C9 | 121.6 (4) |
C7—N1—H1 | 125.9 | C11—C10—C9 | 120.7 (4) |
C8—N1—H1 | 125.9 | C12—C11—C10 | 121.6 (5) |
C7—N2—C9 | 105.8 (3) | C12—C11—H11 | 130.6 |
O1—N3—O2 | 125.4 (5) | C10—C11—H11 | 107.8 |
O1—N3—C6 | 117.0 (4) | C13—C12—C11 | 119.6 (5) |
O2—N3—C6 | 117.6 (5) | C13—C12—H12 | 120.0 |
C6—C1—C2 | 117.7 (4) | C11—C12—H12 | 120.4 |
C6—C1—C7 | 123.2 (4) | C12—C13—C14 | 120.6 (5) |
C2—C1—C7 | 119.0 (4) | C12—C13—H13 | 119.8 |
C3—C2—C1 | 120.0 (5) | C14—C13—H13 | 119.5 |
C3—C2—H2 | 121.5 | C13—C14—C15 | 119.7 (5) |
C1—C2—H2 | 118.5 | C13—C14—H14 | 120.1 |
C4—C3—C2 | 120.6 (6) | C15—C14—H14 | 120.2 |
C4—C3—H3 | 120.0 | C10—C15—C14 | 120.7 (5) |
C2—C3—H3 | 119.4 | C10—C15—H15 | 120.8 |
C5—C4—C3 | 120.5 (6) | C14—C15—H15 | 118.4 |
C5—C4—H4 | 121.3 | C21—C16—C17 | 118.5 (4) |
C3—C4—H4 | 118.1 | C21—C16—C8 | 121.2 (4) |
C4—C5—C6 | 119.5 (6) | C17—C16—C8 | 120.2 (4) |
C4—C5—H5 | 121.4 | C18—C17—C16 | 120.8 (4) |
C6—C5—H5 | 119.1 | C18—C17—H17 | 119.3 |
C1—C6—C5 | 121.6 (5) | C16—C17—H17 | 119.9 |
C1—C6—N3 | 121.7 (4) | C19—C18—C17 | 119.7 (5) |
C5—C6—N3 | 116.7 (5) | C19—C18—H18 | 120.1 |
N2—C7—N1 | 110.6 (3) | C17—C18—H18 | 120.2 |
N2—C7—C1 | 126.2 (3) | C20—C19—C18 | 120.7 (5) |
N1—C7—C1 | 123.1 (3) | C20—C19—H19 | 119.0 |
C9—C8—N1 | 105.7 (3) | C18—C19—H19 | 120.3 |
C9—C8—C16 | 133.4 (4) | C19—C20—C21 | 119.7 (5) |
N1—C8—C16 | 120.8 (3) | C19—C20—H20 | 119.8 |
C8—C9—N2 | 109.7 (3) | C21—C20—H20 | 120.4 |
C8—C9—C10 | 130.5 (4) | C20—C21—C16 | 120.6 (5) |
N2—C9—C10 | 119.8 (3) | C20—C21—H21 | 119.7 |
C15—C10—C11 | 117.7 (4) | C16—C21—H21 | 119.7 |
C6—C1—C2—C3 | −1.2 (6) | C16—C8—C9—C10 | −5.7 (7) |
C7—C1—C2—C3 | 175.0 (4) | C7—N2—C9—C8 | 0.3 (4) |
C1—C2—C3—C4 | −1.1 (8) | C7—N2—C9—C10 | −178.3 (4) |
C2—C3—C4—C5 | 1.8 (9) | C8—C9—C10—C15 | −33.1 (6) |
C3—C4—C5—C6 | −0.2 (8) | N2—C9—C10—C15 | 145.2 (4) |
C2—C1—C6—C5 | 2.9 (6) | C8—C9—C10—C11 | 146.6 (4) |
C7—C1—C6—C5 | −173.2 (4) | N2—C9—C10—C11 | −35.1 (5) |
C2—C1—C6—N3 | −174.9 (4) | C15—C10—C11—C12 | 0.9 (6) |
C7—C1—C6—N3 | 9.1 (6) | C9—C10—C11—C12 | −178.8 (4) |
C4—C5—C6—C1 | −2.2 (7) | C10—C11—C12—C13 | −0.4 (7) |
C4—C5—C6—N3 | 175.7 (5) | C11—C12—C13—C14 | −0.3 (8) |
O1—N3—C6—C1 | 42.3 (6) | C12—C13—C14—C15 | 0.5 (7) |
O2—N3—C6—C1 | −140.0 (5) | C11—C10—C15—C14 | −0.7 (6) |
O1—N3—C6—C5 | −135.6 (4) | C9—C10—C15—C14 | 179.1 (4) |
O2—N3—C6—C5 | 42.1 (6) | C13—C14—C15—C10 | 0.0 (7) |
C9—N2—C7—N1 | 0.5 (4) | C9—C8—C16—C21 | 139.2 (5) |
C9—N2—C7—C1 | 177.0 (4) | N1—C8—C16—C21 | −44.3 (6) |
C8—N1—C7—N2 | −1.1 (4) | C9—C8—C16—C17 | −44.0 (7) |
C8—N1—C7—C1 | −177.7 (4) | N1—C8—C16—C17 | 132.5 (4) |
C6—C1—C7—N2 | 44.3 (6) | C21—C16—C17—C18 | −0.7 (6) |
C2—C1—C7—N2 | −131.7 (4) | C8—C16—C17—C18 | −177.5 (4) |
C6—C1—C7—N1 | −139.7 (4) | C16—C17—C18—C19 | 1.8 (7) |
C2—C1—C7—N1 | 44.3 (6) | C17—C18—C19—C20 | −2.1 (8) |
C7—N1—C8—C9 | 1.3 (4) | C18—C19—C20—C21 | 1.3 (8) |
C7—N1—C8—C16 | −176.1 (4) | C19—C20—C21—C16 | −0.2 (8) |
N1—C8—C9—N2 | −1.0 (4) | C17—C16—C21—C20 | −0.1 (6) |
C16—C8—C9—N2 | 175.9 (4) | C8—C16—C21—C20 | 176.7 (4) |
N1—C8—C9—C10 | 177.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N2i | 0.86 | 2.10 | 2.942 (5) | 165 |
Symmetry code: (i) x, −y, z+1/2. |
C21H15N3O2·C2H3N | F(000) = 1600 |
Mr = 382.41 | Dx = 1.247 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 24379 reflections |
a = 9.111 (2) Å | θ = 2.2–25.3° |
b = 18.830 (4) Å | µ = 0.08 mm−1 |
c = 23.754 (5) Å | T = 293 K |
V = 4075.2 (15) Å3 | Plate, yellow |
Z = 8 | 0.50 × 0.09 × 0.05 mm |
Nonius KappaCCD diffractometer | 1506 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.080 |
Graphite monochromator | θmax = 25.0°, θmin = 2.2° |
ϕ– and ω scans | h = 0→10 |
6703 measured reflections | k = 0→22 |
3584 independent reflections | l = −28→28 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0394P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.81 | (Δ/σ)max < 0.001 |
3584 reflections | Δρmax = 0.15 e Å−3 |
263 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0038 (4) |
C21H15N3O2·C2H3N | V = 4075.2 (15) Å3 |
Mr = 382.41 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 9.111 (2) Å | µ = 0.08 mm−1 |
b = 18.830 (4) Å | T = 293 K |
c = 23.754 (5) Å | 0.50 × 0.09 × 0.05 mm |
Nonius KappaCCD diffractometer | 1506 reflections with I > 2σ(I) |
6703 measured reflections | Rint = 0.080 |
3584 independent reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 0.81 | Δρmax = 0.15 e Å−3 |
3584 reflections | Δρmin = −0.16 e Å−3 |
263 parameters |
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 | 0.4034 (2) | 0.07349 (10) | 0.74120 (8) | 0.0429 (5) | |
H1 | 0.3212 | 0.0691 | 0.7681 | 0.051* | |
N2 | 0.6218 (2) | 0.05601 (10) | 0.70178 (8) | 0.0434 (5) | |
N3 | 0.6575 (3) | −0.10449 (13) | 0.72208 (11) | 0.0680 (7) | |
N4 | 0.7829 (6) | −0.0663 (3) | 0.5086 (2) | 0.158 (2) | |
O1 | 0.5569 (3) | −0.09679 (11) | 0.68841 (8) | 0.0854 (7) | |
O2 | 0.7726 (3) | −0.13453 (14) | 0.71084 (9) | 0.1177 (10) | |
C1 | 0.5680 (3) | −0.01302 (13) | 0.78898 (10) | 0.0417 (6) | |
C2 | 0.5409 (3) | 0.00577 (15) | 0.84461 (12) | 0.0589 (8) | |
H2 | 0.4956 | 0.0508 | 0.8523 | 0.071* | |
C3 | 0.5785 (3) | −0.03916 (19) | 0.88872 (12) | 0.0779 (10) | |
H3 | 0.5551 | −0.0259 | 0.9267 | 0.094* | |
C4 | 0.6486 (4) | −0.10247 (18) | 0.87748 (13) | 0.0814 (10) | |
H4 | 0.6775 | −0.1328 | 0.9080 | 0.098* | |
C5 | 0.6778 (3) | −0.12183 (15) | 0.82327 (13) | 0.0677 (9) | |
H5 | 0.7279 | −0.1652 | 0.8144 | 0.081* | |
C6 | 0.6355 (3) | −0.07766 (14) | 0.77963 (11) | 0.0487 (7) | |
C7 | 0.5321 (3) | 0.03758 (12) | 0.74350 (10) | 0.0415 (6) | |
C8 | 0.4079 (3) | 0.11710 (13) | 0.69452 (9) | 0.0423 (6) | |
C9 | 0.5441 (3) | 0.10624 (13) | 0.67071 (9) | 0.0415 (6) | |
C10 | 0.6158 (3) | 0.14148 (15) | 0.62226 (10) | 0.0473 (7) | |
C11 | 0.7147 (3) | 0.10408 (15) | 0.58886 (10) | 0.0568 (8) | |
H11 | 0.7353 | 0.0552 | 0.5974 | 0.068* | |
C12 | 0.7845 (3) | 0.1364 (2) | 0.54365 (11) | 0.0729 (9) | |
H12 | 0.8535 | 0.1102 | 0.5213 | 0.088* | |
C13 | 0.7544 (4) | 0.2055 (2) | 0.53050 (12) | 0.0801 (11) | |
H13 | 0.8013 | 0.2279 | 0.4989 | 0.096* | |
C14 | 0.6562 (4) | 0.24378 (18) | 0.56297 (13) | 0.0784 (10) | |
H14 | 0.6358 | 0.2922 | 0.5531 | 0.094* | |
C15 | 0.5884 (3) | 0.21192 (15) | 0.60868 (11) | 0.0605 (8) | |
H15 | 0.5219 | 0.2384 | 0.6320 | 0.073* | |
C16 | 0.2788 (3) | 0.16029 (13) | 0.67881 (11) | 0.0450 (7) | |
C17 | 0.2335 (3) | 0.16581 (15) | 0.62305 (11) | 0.0588 (8) | |
H17 | 0.2907 | 0.1432 | 0.5942 | 0.071* | |
C18 | 0.1072 (3) | 0.20251 (17) | 0.60922 (13) | 0.0701 (9) | |
H18 | 0.0768 | 0.2065 | 0.5706 | 0.084* | |
C19 | 0.0237 (3) | 0.23444 (15) | 0.65040 (14) | 0.0682 (9) | |
H19 | −0.0641 | 0.2599 | 0.6407 | 0.082* | |
C20 | 0.0671 (3) | 0.23033 (14) | 0.70607 (13) | 0.0601 (8) | |
H20 | 0.0079 | 0.2516 | 0.7349 | 0.072* | |
C21 | 0.1953 (3) | 0.19412 (13) | 0.71993 (11) | 0.0492 (7) | |
H21 | 0.2280 | 0.1930 | 0.7583 | 0.059* | |
C22 | 0.6739 (8) | −0.0766 (3) | 0.5277 (2) | 0.120 (2) | |
C23 | 0.5327 (6) | −0.0861 (3) | 0.55276 (19) | 0.174 (2) | |
H23A | 0.4753 | −0.1182 | 0.5303 | 0.208* | |
H23B | 0.4854 | −0.0406 | 0.5539 | 0.208* | |
H23C | 0.5415 | −0.1046 | 0.5903 | 0.208* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0359 (13) | 0.0421 (13) | 0.0506 (13) | 0.0021 (11) | 0.0019 (10) | 0.0041 (11) |
N2 | 0.0429 (13) | 0.0400 (13) | 0.0473 (12) | −0.0003 (11) | 0.0018 (11) | 0.0031 (10) |
N3 | 0.086 (2) | 0.0478 (17) | 0.0698 (18) | 0.0050 (16) | 0.0076 (17) | 0.0002 (14) |
N4 | 0.225 (6) | 0.134 (4) | 0.115 (4) | −0.007 (4) | 0.004 (3) | −0.005 (3) |
O1 | 0.118 (2) | 0.0697 (15) | 0.0687 (14) | −0.0114 (14) | −0.0172 (14) | −0.0132 (12) |
O2 | 0.125 (2) | 0.126 (2) | 0.1024 (18) | 0.0546 (19) | 0.0255 (16) | −0.0161 (15) |
C1 | 0.0342 (15) | 0.0418 (17) | 0.0491 (17) | −0.0031 (13) | −0.0013 (13) | 0.0021 (13) |
C2 | 0.064 (2) | 0.053 (2) | 0.0590 (19) | 0.0042 (16) | 0.0033 (16) | 0.0022 (16) |
C3 | 0.095 (3) | 0.082 (3) | 0.0565 (19) | 0.007 (2) | 0.0043 (19) | 0.0074 (19) |
C4 | 0.101 (3) | 0.080 (3) | 0.063 (2) | 0.014 (2) | −0.004 (2) | 0.0192 (19) |
C5 | 0.077 (2) | 0.0472 (19) | 0.079 (2) | 0.0146 (16) | 0.0010 (18) | 0.0149 (17) |
C6 | 0.0525 (18) | 0.0452 (18) | 0.0485 (16) | 0.0003 (14) | 0.0043 (14) | −0.0008 (15) |
C7 | 0.0378 (16) | 0.0362 (16) | 0.0506 (16) | 0.0008 (13) | −0.0039 (14) | −0.0032 (13) |
C8 | 0.0369 (16) | 0.0435 (16) | 0.0465 (15) | 0.0009 (13) | −0.0019 (13) | 0.0021 (13) |
C9 | 0.0399 (16) | 0.0403 (16) | 0.0443 (14) | 0.0006 (13) | 0.0005 (13) | 0.0017 (12) |
C10 | 0.0392 (17) | 0.0532 (19) | 0.0496 (16) | −0.0017 (14) | −0.0027 (13) | 0.0016 (14) |
C11 | 0.058 (2) | 0.064 (2) | 0.0490 (16) | −0.0009 (17) | 0.0008 (15) | −0.0014 (15) |
C12 | 0.068 (2) | 0.096 (3) | 0.0547 (18) | −0.003 (2) | 0.0076 (17) | −0.0025 (18) |
C13 | 0.068 (3) | 0.112 (3) | 0.061 (2) | −0.019 (2) | 0.0026 (18) | 0.020 (2) |
C14 | 0.073 (2) | 0.080 (2) | 0.082 (2) | −0.006 (2) | −0.0022 (19) | 0.036 (2) |
C15 | 0.053 (2) | 0.060 (2) | 0.0687 (19) | 0.0002 (16) | 0.0052 (16) | 0.0132 (16) |
C16 | 0.0387 (16) | 0.0420 (17) | 0.0542 (16) | −0.0010 (13) | −0.0013 (14) | 0.0061 (13) |
C17 | 0.0455 (19) | 0.073 (2) | 0.0576 (18) | 0.0015 (16) | −0.0045 (15) | 0.0044 (15) |
C18 | 0.053 (2) | 0.083 (2) | 0.074 (2) | 0.0032 (19) | −0.0129 (18) | 0.0149 (18) |
C19 | 0.045 (2) | 0.058 (2) | 0.101 (3) | 0.0060 (16) | −0.0112 (19) | 0.0220 (19) |
C20 | 0.051 (2) | 0.0457 (19) | 0.083 (2) | 0.0045 (15) | 0.0090 (17) | 0.0076 (16) |
C21 | 0.0439 (17) | 0.0415 (16) | 0.0621 (17) | −0.0001 (14) | −0.0014 (14) | 0.0080 (14) |
C22 | 0.198 (8) | 0.077 (3) | 0.084 (4) | −0.028 (5) | −0.022 (4) | 0.005 (3) |
C23 | 0.175 (6) | 0.216 (6) | 0.130 (4) | −0.069 (5) | −0.043 (4) | 0.054 (4) |
N1—C7 | 1.355 (3) | C11—C12 | 1.388 (3) |
N1—C8 | 1.380 (3) | C11—H11 | 0.9602 |
N1—H1 | 0.9883 | C12—C13 | 1.366 (4) |
N2—C7 | 1.331 (3) | C12—H12 | 0.9600 |
N2—C9 | 1.393 (3) | C13—C14 | 1.384 (4) |
N3—O2 | 1.222 (3) | C13—H13 | 0.9601 |
N3—O1 | 1.225 (3) | C14—C15 | 1.386 (3) |
N3—C6 | 1.471 (3) | C14—H14 | 0.9602 |
N4—C22 | 1.110 (6) | C15—H15 | 0.9600 |
C1—C6 | 1.381 (3) | C16—C17 | 1.391 (3) |
C1—C2 | 1.390 (3) | C16—C21 | 1.393 (3) |
C1—C7 | 1.477 (3) | C17—C18 | 1.382 (3) |
C2—C3 | 1.390 (3) | C17—H17 | 0.9601 |
C2—H2 | 0.9601 | C18—C19 | 1.378 (4) |
C3—C4 | 1.378 (4) | C18—H18 | 0.9600 |
C3—H3 | 0.9599 | C19—C20 | 1.383 (3) |
C4—C5 | 1.364 (4) | C19—H19 | 0.9602 |
C4—H4 | 0.9600 | C20—C21 | 1.392 (3) |
C5—C6 | 1.384 (3) | C20—H20 | 0.9596 |
C5—H5 | 0.9599 | C21—H21 | 0.9601 |
C8—C9 | 1.379 (3) | C22—C23 | 1.429 (6) |
C8—C16 | 1.478 (3) | C23—H23A | 0.9600 |
C9—C10 | 1.480 (3) | C23—H23B | 0.9599 |
C10—C15 | 1.388 (3) | C23—H23C | 0.9602 |
C10—C11 | 1.392 (3) | ||
C7—N1—C8 | 107.7 (2) | C10—C11—H11 | 119.3 |
C7—N1—H1 | 126.0 | C13—C12—C11 | 120.2 (3) |
C8—N1—H1 | 126.4 | C13—C12—H12 | 119.6 |
C7—N2—C9 | 105.0 (2) | C11—C12—H12 | 120.2 |
O2—N3—O1 | 123.7 (3) | C12—C13—C14 | 119.9 (3) |
O2—N3—C6 | 118.6 (3) | C12—C13—H13 | 120.5 |
O1—N3—C6 | 117.7 (3) | C14—C13—H13 | 119.7 |
C6—C1—C2 | 117.2 (2) | C13—C14—C15 | 120.0 (3) |
C6—C1—C7 | 123.3 (2) | C13—C14—H14 | 118.9 |
C2—C1—C7 | 119.4 (2) | C15—C14—H14 | 121.1 |
C3—C2—C1 | 121.2 (3) | C14—C15—C10 | 121.1 (3) |
C3—C2—H2 | 120.0 | C14—C15—H15 | 120.6 |
C1—C2—H2 | 118.8 | C10—C15—H15 | 118.4 |
C4—C3—C2 | 119.7 (3) | C17—C16—C21 | 118.1 (2) |
C4—C3—H3 | 120.7 | C17—C16—C8 | 121.2 (2) |
C2—C3—H3 | 119.6 | C21—C16—C8 | 120.6 (2) |
C5—C4—C3 | 120.3 (3) | C18—C17—C16 | 120.7 (3) |
C5—C4—H4 | 120.0 | C18—C17—H17 | 120.3 |
C3—C4—H4 | 119.7 | C16—C17—H17 | 119.0 |
C4—C5—C6 | 119.5 (3) | C19—C18—C17 | 120.6 (3) |
C4—C5—H5 | 121.9 | C19—C18—H18 | 119.0 |
C6—C5—H5 | 118.6 | C17—C18—H18 | 120.4 |
C1—C6—C5 | 122.2 (2) | C18—C19—C20 | 119.8 (3) |
C1—C6—N3 | 120.8 (2) | C18—C19—H19 | 120.5 |
C5—C6—N3 | 116.9 (2) | C20—C19—H19 | 119.7 |
N2—C7—N1 | 111.8 (2) | C19—C20—C21 | 119.6 (3) |
N2—C7—C1 | 125.2 (2) | C19—C20—H20 | 119.9 |
N1—C7—C1 | 122.9 (2) | C21—C20—H20 | 120.5 |
C9—C8—N1 | 105.5 (2) | C20—C21—C16 | 121.1 (2) |
C9—C8—C16 | 134.0 (2) | C20—C21—H21 | 119.7 |
N1—C8—C16 | 120.4 (2) | C16—C21—H21 | 119.1 |
C8—C9—N2 | 109.9 (2) | N4—C22—C23 | 177.2 (7) |
C8—C9—C10 | 130.5 (2) | C22—C23—H23A | 109.8 |
N2—C9—C10 | 119.5 (2) | C22—C23—H23B | 107.7 |
C15—C10—C11 | 117.9 (2) | H23A—C23—H23B | 109.5 |
C15—C10—C9 | 122.0 (2) | C22—C23—H23C | 110.9 |
C11—C10—C9 | 120.1 (3) | H23A—C23—H23C | 109.5 |
C12—C11—C10 | 121.0 (3) | H23B—C23—H23C | 109.5 |
C12—C11—H11 | 119.6 | ||
C6—C1—C2—C3 | −0.8 (4) | C16—C8—C9—C10 | 7.5 (5) |
C7—C1—C2—C3 | −177.4 (2) | C7—N2—C9—C8 | −0.1 (3) |
C1—C2—C3—C4 | 2.2 (5) | C7—N2—C9—C10 | 176.6 (2) |
C2—C3—C4—C5 | −1.6 (5) | C8—C9—C10—C15 | 31.1 (4) |
C3—C4—C5—C6 | −0.5 (5) | N2—C9—C10—C15 | −144.7 (2) |
C2—C1—C6—C5 | −1.4 (4) | C8—C9—C10—C11 | −149.3 (3) |
C7—C1—C6—C5 | 175.1 (2) | N2—C9—C10—C11 | 34.9 (3) |
C2—C1—C6—N3 | 174.9 (2) | C15—C10—C11—C12 | 0.4 (4) |
C7—C1—C6—N3 | −8.6 (4) | C9—C10—C11—C12 | −179.2 (2) |
C4—C5—C6—C1 | 2.0 (4) | C10—C11—C12—C13 | −1.4 (4) |
C4—C5—C6—N3 | −174.4 (3) | C11—C12—C13—C14 | 1.2 (5) |
O2—N3—C6—C1 | 140.3 (3) | C12—C13—C14—C15 | −0.1 (5) |
O1—N3—C6—C1 | −41.5 (4) | C13—C14—C15—C10 | −0.9 (4) |
O2—N3—C6—C5 | −43.3 (4) | C11—C10—C15—C14 | 0.7 (4) |
O1—N3—C6—C5 | 135.0 (3) | C9—C10—C15—C14 | −179.7 (2) |
C9—N2—C7—N1 | −0.7 (3) | C9—C8—C16—C17 | 40.0 (4) |
C9—N2—C7—C1 | −177.9 (2) | N1—C8—C16—C17 | −136.8 (2) |
C8—N1—C7—N2 | 1.2 (3) | C9—C8—C16—C21 | −142.9 (3) |
C8—N1—C7—C1 | 178.4 (2) | N1—C8—C16—C21 | 40.3 (3) |
C6—C1—C7—N2 | −45.3 (4) | C21—C16—C17—C18 | −1.5 (4) |
C2—C1—C7—N2 | 131.1 (3) | C8—C16—C17—C18 | 175.7 (2) |
C6—C1—C7—N1 | 137.8 (2) | C16—C17—C18—C19 | 0.1 (4) |
C2—C1—C7—N1 | −45.8 (3) | C17—C18—C19—C20 | 0.6 (5) |
C7—N1—C8—C9 | −1.2 (3) | C18—C19—C20—C21 | 0.2 (4) |
C7—N1—C8—C16 | 176.5 (2) | C19—C20—C21—C16 | −1.7 (4) |
N1—C8—C9—N2 | 0.8 (3) | C17—C16—C21—C20 | 2.3 (4) |
C16—C8—C9—N2 | −176.4 (2) | C8—C16—C21—C20 | −175.0 (2) |
N1—C8—C9—C10 | −175.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N2i | 0.99 | 1.97 | 2.920 (3) | 161 |
Symmetry code: (i) x−1/2, y, −z+3/2. |
C21H15N3O2·CH4O | F(000) = 1568 |
Mr = 373.40 | Dx = 1.277 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 22154 reflections |
a = 11.728 (2) Å | θ = 2.2–25.0° |
b = 11.365 (2) Å | µ = 0.09 mm−1 |
c = 29.241 (6) Å | T = 293 K |
β = 94.62 (2)° | Plate, yellow |
V = 3884.8 (12) Å3 | 0.20 × 0.20 × 0.05 mm |
Z = 8 |
Nonius Kappa CCD diffractometer | 2718 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.105 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
ϕ– and ω– scans | h = 0→13 |
22154 measured reflections | k = 0→13 |
6747 independent reflections | l = −34→34 |
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 0.88 | w = 1/[σ2(Fo2) + (0.0689P)2] where P = (Fo2 + 2Fc2)/3 |
6747 reflections | (Δ/σ)max = 0.001 |
505 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C21H15N3O2·CH4O | V = 3884.8 (12) Å3 |
Mr = 373.40 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.728 (2) Å | µ = 0.09 mm−1 |
b = 11.365 (2) Å | T = 293 K |
c = 29.241 (6) Å | 0.20 × 0.20 × 0.05 mm |
β = 94.62 (2)° |
Nonius Kappa CCD diffractometer | 2718 reflections with I > 2σ(I) |
22154 measured reflections | Rint = 0.105 |
6747 independent reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 0.88 | Δρmax = 0.17 e Å−3 |
6747 reflections | Δρmin = −0.18 e Å−3 |
505 parameters |
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 | ||
O1a | 0.6772 (2) | 0.5838 (3) | 0.41409 (8) | 0.0944 (11) | |
O2a | 0.8607 (2) | 0.5836 (3) | 0.41847 (8) | 0.0928 (10) | |
N1a | 0.69010 (19) | 0.5116 (3) | 0.17410 (9) | 0.0442 (8) | |
H1a | 0.6453 | 0.4575 | 0.1828 | 0.053* | |
N2a | 0.81539 (18) | 0.6566 (3) | 0.17794 (9) | 0.0438 (8) | |
N3a | 0.7679 (3) | 0.5816 (3) | 0.39644 (10) | 0.0638 (9) | |
C1a | 0.7585 (2) | 0.5805 (3) | 0.25228 (10) | 0.0411 (9) | |
C2a | 0.8460 (3) | 0.6361 (3) | 0.27870 (11) | 0.0543 (11) | |
H2a | 0.9057 | 0.6744 | 0.2637 | 0.065* | |
C3a | 0.8509 (3) | 0.6364 (3) | 0.32602 (11) | 0.0532 (11) | |
H3a | 0.9123 | 0.6758 | 0.3434 | 0.064* | |
C4a | 0.7657 (3) | 0.5798 (3) | 0.34658 (10) | 0.0469 (10) | |
C5a | 0.6775 (3) | 0.5225 (3) | 0.32200 (11) | 0.0506 (10) | |
H5a | 0.6185 | 0.4840 | 0.3373 | 0.061* | |
C6a | 0.6754 (2) | 0.5220 (3) | 0.27496 (11) | 0.0472 (10) | |
H6a | 0.6156 | 0.4815 | 0.2570 | 0.057* | |
C7a | 0.7561 (2) | 0.5826 (3) | 0.20230 (10) | 0.0402 (9) | |
C8a | 0.7060 (2) | 0.5396 (3) | 0.12947 (11) | 0.0438 (10) | |
C9a | 0.7845 (2) | 0.6304 (3) | 0.13254 (10) | 0.0427 (9) | |
C10a | 0.8308 (3) | 0.6980 (3) | 0.09517 (10) | 0.0454 (10) | |
C11a | 0.9469 (3) | 0.7220 (4) | 0.09614 (12) | 0.0698 (13) | |
H11a | 0.9970 | 0.6940 | 0.1214 | 0.084* | |
C12a | 0.9910 (3) | 0.7856 (4) | 0.06090 (13) | 0.0889 (16) | |
H12a | 1.0714 | 0.8024 | 0.0615 | 0.107* | |
C13a | 0.9190 (3) | 0.8264 (4) | 0.02500 (12) | 0.0737 (13) | |
H13a | 0.9503 | 0.8702 | 0.0009 | 0.088* | |
C14a | 0.8041 (3) | 0.8044 (4) | 0.02371 (11) | 0.0642 (12) | |
H14a | 0.7546 | 0.8333 | −0.0016 | 0.077* | |
C15a | 0.7602 (3) | 0.7413 (4) | 0.05872 (11) | 0.0546 (11) | |
H15a | 0.6795 | 0.7262 | 0.0579 | 0.065* | |
C16a | 0.6503 (3) | 0.4757 (3) | 0.09046 (11) | 0.0494 (10) | |
C17a | 0.7065 (3) | 0.4511 (4) | 0.05184 (12) | 0.0612 (11) | |
H17a | 0.7846 | 0.4755 | 0.0508 | 0.073* | |
C18a | 0.6522 (4) | 0.3897 (4) | 0.01599 (13) | 0.0791 (14) | |
H18a | 0.6933 | 0.3723 | −0.0103 | 0.095* | |
C19a | 0.5412 (4) | 0.3519 (4) | 0.01767 (15) | 0.0893 (15) | |
H19a | 0.5030 | 0.3109 | −0.0079 | 0.107* | |
C20a | 0.4840 (3) | 0.3761 (4) | 0.05563 (16) | 0.0887 (15) | |
H20a | 0.4071 | 0.3477 | 0.0563 | 0.106* | |
C21a | 0.5382 (3) | 0.4384 (4) | 0.09179 (12) | 0.0667 (12) | |
H21a | 0.4979 | 0.4561 | 0.1183 | 0.080* | |
N1b | 0.18791 (19) | 0.5121 (3) | 0.24788 (9) | 0.0446 (8) | |
H1b | 0.1369 | 0.4647 | 0.2566 | 0.054* | |
O1b | 0.3684 (3) | 0.5780 (3) | 0.49230 (9) | 0.0974 (11) | |
O2b | 0.1878 (3) | 0.6186 (3) | 0.48783 (9) | 0.1040 (12) | |
N2b | 0.33046 (19) | 0.6392 (3) | 0.25154 (9) | 0.0421 (8) | |
N3b | 0.2759 (3) | 0.5938 (3) | 0.47055 (11) | 0.0730 (10) | |
C1b | 0.2650 (2) | 0.5750 (3) | 0.32610 (10) | 0.0430 (9) | |
C2b | 0.3682 (3) | 0.5957 (3) | 0.35227 (11) | 0.0543 (10) | |
H2b | 0.4367 | 0.6073 | 0.3369 | 0.065* | |
C3b | 0.3718 (3) | 0.5991 (4) | 0.39940 (11) | 0.0563 (11) | |
H3b | 0.4423 | 0.6115 | 0.4178 | 0.068* | |
C4b | 0.2722 (3) | 0.5852 (3) | 0.42034 (11) | 0.0523 (10) | |
C5b | 0.1692 (3) | 0.5639 (4) | 0.39558 (12) | 0.0648 (12) | |
H5b | 0.1018 | 0.5540 | 0.4118 | 0.078* | |
C6b | 0.1669 (3) | 0.5587 (3) | 0.34865 (11) | 0.0551 (11) | |
H6b | 0.0962 | 0.5436 | 0.3307 | 0.066* | |
C7b | 0.2625 (2) | 0.5757 (3) | 0.27591 (11) | 0.0428 (9) | |
C8b | 0.2079 (2) | 0.5366 (3) | 0.20302 (11) | 0.0415 (9) | |
C9b | 0.2965 (2) | 0.6173 (3) | 0.20595 (11) | 0.0426 (9) | |
C10b | 0.3505 (3) | 0.6807 (3) | 0.16992 (10) | 0.0439 (9) | |
C11b | 0.4659 (3) | 0.7104 (3) | 0.17592 (11) | 0.0521 (10) | |
H11b | 0.5094 | 0.6855 | 0.2035 | 0.063* | |
C12b | 0.5186 (3) | 0.7756 (4) | 0.14338 (13) | 0.0591 (11) | |
H12b | 0.5981 | 0.7959 | 0.1484 | 0.071* | |
C13b | 0.4555 (3) | 0.8105 (4) | 0.10364 (12) | 0.0618 (11) | |
H13b | 0.4921 | 0.8550 | 0.0811 | 0.074* | |
C14b | 0.3417 (3) | 0.7820 (3) | 0.09691 (11) | 0.0568 (11) | |
H14b | 0.2978 | 0.8063 | 0.0694 | 0.068* | |
C15b | 0.2905 (3) | 0.7192 (3) | 0.12961 (11) | 0.0508 (10) | |
H15b | 0.2106 | 0.7007 | 0.1245 | 0.061* | |
C16b | 0.1429 (3) | 0.4759 (3) | 0.16525 (11) | 0.0467 (10) | |
C17b | 0.1915 (3) | 0.4505 (3) | 0.12422 (12) | 0.0570 (11) | |
H17b | 0.2692 | 0.4736 | 0.1211 | 0.068* | |
C18b | 0.1285 (3) | 0.3928 (4) | 0.08869 (13) | 0.0724 (13) | |
H18b | 0.1633 | 0.3762 | 0.0608 | 0.087* | |
C19b | 0.0174 (4) | 0.3599 (4) | 0.09315 (15) | 0.0763 (13) | |
H19b | −0.0260 | 0.3201 | 0.0686 | 0.092* | |
C20b | −0.0317 (3) | 0.3831 (4) | 0.13311 (15) | 0.0655 (12) | |
H20b | −0.1090 | 0.3584 | 0.1359 | 0.079* | |
C21b | 0.0300 (3) | 0.4413 (3) | 0.16882 (12) | 0.0552 (11) | |
H21b | −0.0059 | 0.4587 | 0.1964 | 0.066* | |
O3a | 0.55378 (17) | 0.3298 (2) | 0.20625 (7) | 0.0594 (7) | |
H3Oa | 0.5805 | 0.2705 | 0.2190 | 0.089* | |
C22a | 0.4354 (3) | 0.3277 (4) | 0.20601 (14) | 0.0981 (16) | |
H22a | 0.4137 | 0.3167 | 0.2367 | 0.118* | |
H22b | 0.4056 | 0.2643 | 0.1869 | 0.118* | |
H22C | 0.4050 | 0.4010 | 0.1941 | 0.118* | |
O3b | 0.94845 (17) | 0.8441 (2) | 0.21350 (7) | 0.0573 (7) | |
H3Ob | 0.9105 | 0.7930 | 0.1996 | 0.086* | |
C22b | 1.0643 (3) | 0.8157 (4) | 0.21422 (15) | 0.0982 (16) | |
H22D | 1.1064 | 0.8615 | 0.2374 | 0.118* | |
H22E | 1.0916 | 0.8328 | 0.1848 | 0.118* | |
H22F | 1.0746 | 0.7335 | 0.2209 | 0.118* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1a | 0.104 (2) | 0.126 (3) | 0.0576 (19) | −0.018 (2) | 0.0329 (16) | −0.0146 (19) |
O2a | 0.106 (2) | 0.129 (3) | 0.0409 (17) | −0.012 (2) | −0.0119 (15) | 0.0023 (18) |
N1a | 0.0478 (15) | 0.050 (2) | 0.0348 (17) | −0.0054 (15) | 0.0028 (13) | 0.0000 (17) |
N2a | 0.0446 (15) | 0.055 (2) | 0.0317 (17) | 0.0007 (15) | 0.0009 (12) | 0.0054 (16) |
N3a | 0.084 (3) | 0.067 (3) | 0.040 (2) | −0.008 (2) | 0.0024 (18) | −0.0041 (19) |
C1a | 0.0432 (19) | 0.045 (3) | 0.035 (2) | −0.0038 (18) | 0.0001 (15) | 0.0006 (19) |
C2a | 0.053 (2) | 0.068 (3) | 0.042 (2) | −0.015 (2) | 0.0047 (16) | 0.005 (2) |
C3a | 0.059 (2) | 0.064 (3) | 0.036 (2) | −0.020 (2) | −0.0011 (16) | −0.002 (2) |
C4a | 0.064 (2) | 0.048 (3) | 0.028 (2) | −0.004 (2) | 0.0016 (17) | −0.001 (2) |
C5a | 0.059 (2) | 0.058 (3) | 0.036 (2) | −0.004 (2) | 0.0097 (16) | 0.006 (2) |
C6a | 0.046 (2) | 0.053 (3) | 0.042 (2) | −0.0117 (18) | 0.0003 (16) | −0.004 (2) |
C7a | 0.0454 (19) | 0.046 (3) | 0.029 (2) | −0.0051 (18) | 0.0006 (15) | −0.001 (2) |
C8a | 0.044 (2) | 0.051 (3) | 0.037 (2) | 0.0057 (18) | 0.0016 (16) | 0.000 (2) |
C9a | 0.0459 (19) | 0.056 (3) | 0.027 (2) | 0.0002 (19) | 0.0017 (15) | 0.0018 (19) |
C10a | 0.052 (2) | 0.049 (3) | 0.035 (2) | 0.0008 (18) | 0.0048 (16) | 0.0014 (19) |
C11a | 0.055 (2) | 0.099 (4) | 0.056 (2) | 0.000 (2) | 0.0062 (18) | 0.029 (3) |
C12a | 0.070 (3) | 0.134 (5) | 0.063 (3) | −0.014 (3) | 0.010 (2) | 0.030 (3) |
C13a | 0.093 (3) | 0.085 (4) | 0.044 (2) | −0.008 (3) | 0.009 (2) | 0.024 (2) |
C14a | 0.084 (3) | 0.071 (4) | 0.037 (2) | 0.000 (2) | −0.0008 (19) | 0.007 (2) |
C15a | 0.059 (2) | 0.066 (3) | 0.038 (2) | 0.005 (2) | 0.0004 (17) | 0.005 (2) |
C16a | 0.055 (2) | 0.050 (3) | 0.042 (2) | 0.0046 (19) | −0.0076 (17) | −0.001 (2) |
C17a | 0.077 (2) | 0.066 (3) | 0.040 (2) | 0.010 (2) | −0.004 (2) | −0.008 (2) |
C18a | 0.114 (3) | 0.077 (4) | 0.044 (3) | 0.020 (3) | −0.008 (2) | −0.019 (3) |
C19a | 0.123 (4) | 0.071 (4) | 0.066 (3) | 0.005 (3) | −0.043 (3) | −0.016 (3) |
C20a | 0.087 (3) | 0.095 (4) | 0.078 (3) | −0.011 (3) | −0.025 (3) | −0.009 (3) |
C21a | 0.074 (3) | 0.072 (4) | 0.052 (3) | −0.004 (2) | −0.0086 (19) | −0.008 (2) |
N1b | 0.0462 (15) | 0.040 (2) | 0.0475 (19) | −0.0078 (14) | 0.0058 (13) | 0.0012 (17) |
O1b | 0.117 (2) | 0.125 (3) | 0.0488 (19) | −0.012 (2) | −0.0035 (16) | 0.0063 (19) |
O2b | 0.118 (2) | 0.141 (4) | 0.0577 (19) | −0.020 (2) | 0.0352 (17) | −0.027 (2) |
N2b | 0.0439 (15) | 0.046 (2) | 0.0365 (17) | −0.0014 (14) | 0.0033 (13) | −0.0017 (16) |
N3b | 0.105 (3) | 0.069 (3) | 0.046 (2) | −0.017 (2) | 0.015 (2) | −0.003 (2) |
C1b | 0.047 (2) | 0.045 (3) | 0.037 (2) | 0.0013 (17) | 0.0048 (17) | 0.0007 (19) |
C2b | 0.051 (2) | 0.067 (3) | 0.045 (2) | −0.0024 (19) | 0.0058 (17) | 0.003 (2) |
C3b | 0.062 (2) | 0.064 (3) | 0.041 (2) | −0.004 (2) | −0.0038 (17) | 0.001 (2) |
C4b | 0.075 (3) | 0.045 (3) | 0.037 (2) | −0.005 (2) | 0.0101 (19) | −0.007 (2) |
C5b | 0.064 (2) | 0.081 (4) | 0.051 (3) | −0.015 (2) | 0.0185 (19) | −0.010 (2) |
C6b | 0.057 (2) | 0.070 (3) | 0.039 (2) | −0.010 (2) | 0.0066 (17) | −0.007 (2) |
C7b | 0.0391 (19) | 0.050 (3) | 0.039 (2) | 0.0029 (18) | 0.0033 (16) | 0.000 (2) |
C8b | 0.047 (2) | 0.043 (3) | 0.034 (2) | 0.0045 (18) | 0.0005 (16) | −0.0007 (19) |
C9b | 0.0434 (19) | 0.048 (3) | 0.036 (2) | 0.0041 (18) | 0.0035 (15) | −0.002 (2) |
C10b | 0.052 (2) | 0.045 (3) | 0.037 (2) | 0.0034 (18) | 0.0096 (16) | −0.0015 (19) |
C11b | 0.054 (2) | 0.055 (3) | 0.048 (2) | 0.0042 (19) | 0.0103 (17) | −0.002 (2) |
C12b | 0.049 (2) | 0.066 (3) | 0.065 (3) | 0.004 (2) | 0.016 (2) | 0.000 (2) |
C13b | 0.078 (3) | 0.057 (3) | 0.053 (3) | −0.003 (2) | 0.025 (2) | 0.001 (2) |
C14b | 0.081 (3) | 0.055 (3) | 0.035 (2) | 0.001 (2) | 0.0086 (18) | 0.003 (2) |
C15b | 0.053 (2) | 0.058 (3) | 0.041 (2) | −0.0024 (19) | 0.0036 (17) | 0.006 (2) |
C16b | 0.050 (2) | 0.042 (3) | 0.047 (2) | 0.0053 (18) | −0.0040 (17) | 0.003 (2) |
C17b | 0.066 (2) | 0.055 (3) | 0.049 (2) | 0.006 (2) | −0.0005 (19) | −0.005 (2) |
C18b | 0.091 (3) | 0.074 (4) | 0.050 (3) | 0.003 (3) | −0.011 (2) | −0.015 (2) |
C19b | 0.086 (3) | 0.062 (4) | 0.074 (3) | 0.006 (3) | −0.033 (2) | −0.006 (3) |
C20b | 0.054 (2) | 0.054 (3) | 0.085 (3) | −0.002 (2) | −0.017 (2) | −0.002 (3) |
C21b | 0.055 (2) | 0.048 (3) | 0.060 (3) | 0.006 (2) | −0.0070 (18) | 0.000 (2) |
O3a | 0.0577 (15) | 0.0487 (19) | 0.0706 (17) | 0.0001 (13) | −0.0023 (11) | 0.0100 (14) |
C22a | 0.070 (3) | 0.088 (4) | 0.133 (4) | 0.007 (3) | −0.013 (2) | 0.030 (3) |
O3b | 0.0548 (14) | 0.0518 (19) | 0.0660 (16) | 0.0021 (12) | 0.0096 (11) | −0.0084 (14) |
C22b | 0.060 (3) | 0.089 (4) | 0.148 (4) | −0.005 (3) | 0.021 (2) | −0.038 (3) |
O1a—N3a | 1.220 (3) | N2b—C7b | 1.325 (4) |
O2a—N3a | 1.219 (3) | N2b—C9b | 1.383 (4) |
N1a—C7a | 1.352 (4) | N3b—C4b | 1.469 (4) |
N1a—C8a | 1.370 (4) | C1b—C6b | 1.383 (4) |
N1a—H1a | 0.8600 | C1b—C2b | 1.399 (4) |
N2a—C7a | 1.333 (4) | C1b—C7b | 1.465 (4) |
N2a—C9a | 1.380 (4) | C2b—C3b | 1.376 (4) |
N3a—C4a | 1.456 (4) | C2b—H2b | 0.9599 |
C1a—C2a | 1.386 (4) | C3b—C4b | 1.371 (4) |
C1a—C6a | 1.392 (4) | C3b—H3b | 0.9599 |
C1a—C7a | 1.460 (4) | C4b—C5b | 1.378 (4) |
C2a—C3a | 1.380 (4) | C5b—C6b | 1.372 (4) |
C2a—H2a | 0.9598 | C5b—H5b | 0.9599 |
C3a—C4a | 1.368 (4) | C6b—H6b | 0.9600 |
C3a—H3a | 0.9598 | C8b—C9b | 1.383 (4) |
C4a—C5a | 1.375 (4) | C8b—C16b | 1.464 (4) |
C5a—C6a | 1.374 (4) | C9b—C10b | 1.463 (4) |
C5a—H5a | 0.9600 | C10b—C11b | 1.392 (4) |
C6a—H6a | 0.9602 | C10b—C15b | 1.394 (4) |
C8a—C9a | 1.381 (4) | C11b—C12b | 1.389 (5) |
C8a—C16a | 1.461 (4) | C11b—H11b | 0.9600 |
C9a—C10a | 1.474 (4) | C12b—C13b | 1.384 (4) |
C10a—C15a | 1.386 (4) | C12b—H12b | 0.9602 |
C10a—C11a | 1.387 (4) | C13b—C14b | 1.372 (4) |
C11a—C12a | 1.392 (5) | C13b—H13b | 0.9598 |
C11a—H11a | 0.9602 | C14b—C15b | 1.370 (4) |
C12a—C13a | 1.374 (5) | C14b—H14b | 0.9600 |
C12a—H12a | 0.9601 | C15b—H15b | 0.9602 |
C13a—C14a | 1.368 (4) | C16b—C21b | 1.393 (4) |
C13a—H13a | 0.9601 | C16b—C17b | 1.399 (4) |
C14a—C15a | 1.383 (4) | C17b—C18b | 1.389 (5) |
C14a—H14a | 0.9597 | C17b—H17b | 0.9600 |
C15a—H15a | 0.9600 | C18b—C19b | 1.372 (5) |
C16a—C17a | 1.381 (4) | C18b—H18b | 0.9596 |
C16a—C21a | 1.385 (4) | C19b—C20b | 1.369 (5) |
C17a—C18a | 1.373 (5) | C19b—H19b | 0.9596 |
C17a—H17a | 0.9600 | C20b—C21b | 1.389 (5) |
C18a—C19a | 1.375 (5) | C20b—H20b | 0.9600 |
C18a—H18a | 0.9599 | C21b—H21b | 0.9600 |
C19a—C20a | 1.370 (5) | O3a—C22a | 1.388 (4) |
C19a—H19a | 0.9599 | O3a—H3Oa | 0.8200 |
C20a—C21a | 1.384 (5) | C22a—H22a | 0.9601 |
C20a—H20a | 0.9600 | C22a—H22b | 0.9599 |
C21a—H21a | 0.9598 | C22a—H22C | 0.9599 |
N1b—C7b | 1.358 (4) | O3b—C22b | 1.395 (4) |
N1b—C8b | 1.379 (4) | O3b—H3Ob | 0.8200 |
N1b—H1b | 0.8600 | C22b—H22D | 0.9598 |
O1b—N3b | 1.226 (3) | C22b—H22E | 0.9600 |
O2b—N3b | 1.220 (4) | C22b—H22F | 0.9600 |
C7a—N1a—C8a | 109.1 (3) | C6b—C1b—C2b | 118.5 (3) |
C7a—N1a—H1a | 125.5 | C6b—C1b—C7b | 121.9 (3) |
C8a—N1a—H1a | 125.5 | C2b—C1b—C7b | 119.6 (3) |
C7a—N2a—C9a | 105.7 (3) | C3b—C2b—C1b | 120.5 (3) |
O2a—N3a—O1a | 123.2 (3) | C3b—C2b—H2b | 120.3 |
O2a—N3a—C4a | 118.2 (3) | C1b—C2b—H2b | 119.2 |
O1a—N3a—C4a | 118.5 (3) | C4b—C3b—C2b | 119.0 (3) |
C2a—C1a—C6a | 117.9 (3) | C4b—C3b—H3b | 119.5 |
C2a—C1a—C7a | 120.3 (3) | C2b—C3b—H3b | 121.5 |
C6a—C1a—C7a | 121.8 (3) | C3b—C4b—C5b | 121.8 (3) |
C3a—C2a—C1a | 121.9 (3) | C3b—C4b—N3b | 118.7 (3) |
C3a—C2a—H2a | 118.9 | C5b—C4b—N3b | 119.4 (3) |
C1a—C2a—H2a | 119.2 | C6b—C5b—C4b | 118.6 (3) |
C4a—C3a—C2a | 117.8 (3) | C6b—C5b—H5b | 122.5 |
C4a—C3a—H3a | 122.0 | C4b—C5b—H5b | 118.9 |
C2a—C3a—H3a | 120.1 | C5b—C6b—C1b | 121.4 (3) |
C3a—C4a—C5a | 122.6 (3) | C5b—C6b—H6b | 120.1 |
C3a—C4a—N3a | 118.6 (3) | C1b—C6b—H6b | 118.5 |
C5a—C4a—N3a | 118.8 (3) | N2b—C7b—N1b | 110.6 (3) |
C6a—C5a—C4a | 118.5 (3) | N2b—C7b—C1b | 125.3 (3) |
C6a—C5a—H5a | 120.7 | N1b—C7b—C1b | 124.1 (3) |
C4a—C5a—H5a | 120.8 | N1b—C8b—C9b | 105.0 (3) |
C5a—C6a—C1a | 121.2 (3) | N1b—C8b—C16b | 120.3 (3) |
C5a—C6a—H6a | 120.2 | C9b—C8b—C16b | 134.6 (3) |
C1a—C6a—H6a | 118.5 | C8b—C9b—N2b | 109.6 (3) |
N2a—C7a—N1a | 110.4 (3) | C8b—C9b—C10b | 130.5 (3) |
N2a—C7a—C1a | 125.2 (3) | N2b—C9b—C10b | 119.9 (3) |
N1a—C7a—C1a | 124.4 (3) | C11b—C10b—C15b | 116.8 (3) |
N1a—C8a—C9a | 104.6 (3) | C11b—C10b—C9b | 120.1 (3) |
N1a—C8a—C16a | 122.8 (3) | C15b—C10b—C9b | 123.0 (3) |
C9a—C8a—C16a | 132.5 (3) | C12b—C11b—C10b | 121.6 (3) |
N2a—C9a—C8a | 110.2 (3) | C12b—C11b—H11b | 119.8 |
N2a—C9a—C10a | 121.1 (3) | C10b—C11b—H11b | 118.7 |
C8a—C9a—C10a | 128.6 (3) | C13b—C12b—C11b | 119.4 (3) |
C15a—C10a—C11a | 118.0 (3) | C13b—C12b—H12b | 120.3 |
C15a—C10a—C9a | 121.5 (3) | C11b—C12b—H12b | 120.2 |
C11a—C10a—C9a | 120.5 (3) | C14b—C13b—C12b | 120.0 (3) |
C10a—C11a—C12a | 120.7 (3) | C14b—C13b—H13b | 120.6 |
C10a—C11a—H11a | 119.3 | C12b—C13b—H13b | 119.4 |
C12a—C11a—H11a | 120.0 | C15b—C14b—C13b | 120.0 (3) |
C13a—C12a—C11a | 119.9 (4) | C15b—C14b—H14b | 119.9 |
C13a—C12a—H12a | 119.3 | C13b—C14b—H14b | 120.1 |
C11a—C12a—H12a | 120.8 | C14b—C15b—C10b | 122.2 (3) |
C14a—C13a—C12a | 120.2 (4) | C14b—C15b—H15b | 118.8 |
C14a—C13a—H13a | 120.5 | C10b—C15b—H15b | 118.9 |
C12a—C13a—H13a | 119.3 | C21b—C16b—C17b | 117.5 (3) |
C13a—C14a—C15a | 119.9 (3) | C21b—C16b—C8b | 121.1 (3) |
C13a—C14a—H14a | 119.5 | C17b—C16b—C8b | 121.4 (3) |
C15a—C14a—H14a | 120.6 | C18b—C17b—C16b | 120.7 (3) |
C14a—C15a—C10a | 121.2 (3) | C18b—C17b—H17b | 120.5 |
C14a—C15a—H15a | 120.0 | C16b—C17b—H17b | 118.8 |
C10a—C15a—H15a | 118.8 | C19b—C18b—C17b | 120.6 (4) |
C17a—C16a—C21a | 118.5 (3) | C19b—C18b—H18b | 119.9 |
C17a—C16a—C8a | 121.8 (3) | C17b—C18b—H18b | 119.5 |
C21a—C16a—C8a | 119.7 (3) | C20b—C19b—C18b | 119.7 (4) |
C18a—C17a—C16a | 120.3 (4) | C20b—C19b—H19b | 119.7 |
C18a—C17a—H17a | 120.6 | C18b—C19b—H19b | 120.6 |
C16a—C17a—H17a | 119.1 | C19b—C20b—C21b | 120.3 (4) |
C17a—C18a—C19a | 120.9 (4) | C19b—C20b—H20b | 118.8 |
C17a—C18a—H18a | 118.9 | C21b—C20b—H20b | 120.9 |
C19a—C18a—H18a | 120.1 | C20b—C21b—C16b | 121.2 (4) |
C20a—C19a—C18a | 119.5 (4) | C20b—C21b—H21b | 119.5 |
C20a—C19a—H19a | 120.0 | C16b—C21b—H21b | 119.3 |
C18a—C19a—H19a | 120.5 | C22a—O3a—H3Oa | 109.5 |
C19a—C20a—C21a | 119.9 (4) | O3a—C22a—H22a | 109.7 |
C19a—C20a—H20a | 118.1 | O3a—C22a—H22b | 109.5 |
C21a—C20a—H20a | 122.0 | H22a—C22a—H22b | 109.5 |
C20a—C21a—C16a | 120.9 (4) | O3a—C22a—H22C | 109.2 |
C20a—C21a—H21a | 119.9 | H22a—C22a—H22C | 109.5 |
C16a—C21a—H21a | 119.3 | H22b—C22a—H22C | 109.5 |
C7b—N1b—C8b | 108.4 (3) | C22b—O3b—H3Ob | 109.5 |
C7b—N1b—H1b | 125.8 | O3b—C22b—H22D | 109.3 |
C8b—N1b—H1b | 125.8 | O3b—C22b—H22E | 109.5 |
C7b—N2b—C9b | 106.3 (3) | H22D—C22b—H22E | 109.5 |
O2b—N3b—O1b | 124.3 (3) | O3b—C22b—H22F | 109.6 |
O2b—N3b—C4b | 118.1 (4) | H22D—C22b—H22F | 109.5 |
O1b—N3b—C4b | 117.6 (3) | H22E—C22b—H22F | 109.5 |
C6a—C1a—C2a—C3a | −1.3 (5) | C6b—C1b—C2b—C3b | 0.3 (6) |
C7a—C1a—C2a—C3a | 179.7 (3) | C7b—C1b—C2b—C3b | 177.9 (4) |
C1a—C2a—C3a—C4a | −0.1 (6) | C1b—C2b—C3b—C4b | −1.8 (6) |
C2a—C3a—C4a—C5a | 0.7 (6) | C2b—C3b—C4b—C5b | 2.2 (6) |
C2a—C3a—C4a—N3a | −178.6 (3) | C2b—C3b—C4b—N3b | −177.6 (4) |
O2a—N3a—C4a—C3a | −32.1 (5) | O2b—N3b—C4b—C3b | 157.2 (4) |
O1a—N3a—C4a—C3a | 146.2 (4) | O1b—N3b—C4b—C3b | −21.2 (6) |
O2a—N3a—C4a—C5a | 148.6 (4) | O2b—N3b—C4b—C5b | −22.6 (6) |
O1a—N3a—C4a—C5a | −33.1 (5) | O1b—N3b—C4b—C5b | 159.0 (4) |
C3a—C4a—C5a—C6a | 0.2 (6) | C3b—C4b—C5b—C6b | −1.2 (6) |
N3a—C4a—C5a—C6a | 179.5 (3) | N3b—C4b—C5b—C6b | 178.6 (4) |
C4a—C5a—C6a—C1a | −1.7 (5) | C4b—C5b—C6b—C1b | −0.4 (6) |
C2a—C1a—C6a—C5a | 2.3 (5) | C2b—C1b—C6b—C5b | 0.8 (6) |
C7a—C1a—C6a—C5a | −178.8 (3) | C7b—C1b—C6b—C5b | −176.8 (4) |
C9a—N2a—C7a—N1a | 0.1 (4) | C9b—N2b—C7b—N1b | 1.2 (4) |
C9a—N2a—C7a—C1a | −177.9 (3) | C9b—N2b—C7b—C1b | −177.7 (3) |
C8a—N1a—C7a—N2a | −0.1 (4) | C8b—N1b—C7b—N2b | −0.6 (4) |
C8a—N1a—C7a—C1a | 177.9 (3) | C8b—N1b—C7b—C1b | 178.3 (3) |
C2a—C1a—C7a—N2a | −17.1 (5) | C6b—C1b—C7b—N2b | 147.3 (4) |
C6a—C1a—C7a—N2a | 164.0 (3) | C2b—C1b—C7b—N2b | −30.2 (5) |
C2a—C1a—C7a—N1a | 165.2 (3) | C6b—C1b—C7b—N1b | −31.5 (6) |
C6a—C1a—C7a—N1a | −13.7 (5) | C2b—C1b—C7b—N1b | 151.0 (3) |
C7a—N1a—C8a—C9a | 0.0 (3) | C7b—N1b—C8b—C9b | −0.3 (3) |
C7a—N1a—C8a—C16a | 177.4 (3) | C7b—N1b—C8b—C16b | 177.2 (3) |
C7a—N2a—C9a—C8a | −0.1 (4) | N1b—C8b—C9b—N2b | 1.1 (3) |
C7a—N2a—C9a—C10a | 178.0 (3) | C16b—C8b—C9b—N2b | −175.9 (3) |
N1a—C8a—C9a—N2a | 0.0 (3) | N1b—C8b—C9b—C10b | −176.1 (3) |
C16a—C8a—C9a—N2a | −177.0 (3) | C16b—C8b—C9b—C10b | 7.0 (6) |
N1a—C8a—C9a—C10a | −177.9 (3) | C7b—N2b—C9b—C8b | −1.4 (4) |
C16a—C8a—C9a—C10a | 5.1 (6) | C7b—N2b—C9b—C10b | 176.0 (3) |
N2a—C9a—C10a—C15a | −131.9 (3) | C8b—C9b—C10b—C11b | −148.4 (4) |
C8a—C9a—C10a—C15a | 45.8 (5) | N2b—C9b—C10b—C11b | 34.7 (5) |
N2a—C9a—C10a—C11a | 46.8 (5) | C8b—C9b—C10b—C15b | 34.7 (6) |
C8a—C9a—C10a—C11a | −135.5 (4) | N2b—C9b—C10b—C15b | −142.1 (3) |
C15a—C10a—C11a—C12a | −1.4 (6) | C15b—C10b—C11b—C12b | 0.3 (5) |
C9a—C10a—C11a—C12a | 179.9 (4) | C9b—C10b—C11b—C12b | −176.8 (3) |
C10a—C11a—C12a—C13a | 0.9 (7) | C10b—C11b—C12b—C13b | −1.1 (5) |
C11a—C12a—C13a—C14a | −0.2 (7) | C11b—C12b—C13b—C14b | 0.8 (6) |
C12a—C13a—C14a—C15a | 0.2 (7) | C12b—C13b—C14b—C15b | 0.2 (6) |
C13a—C14a—C15a—C10a | −0.8 (6) | C13b—C14b—C15b—C10b | −1.0 (6) |
C11a—C10a—C15a—C14a | 1.4 (6) | C11b—C10b—C15b—C14b | 0.8 (5) |
C9a—C10a—C15a—C14a | −179.9 (4) | C9b—C10b—C15b—C14b | 177.7 (3) |
N1a—C8a—C16a—C17a | −141.1 (3) | N1b—C8b—C16b—C21b | 32.4 (5) |
C9a—C8a—C16a—C17a | 35.5 (6) | C9b—C8b—C16b—C21b | −151.0 (4) |
N1a—C8a—C16a—C21a | 38.9 (5) | N1b—C8b—C16b—C17b | −147.8 (3) |
C9a—C8a—C16a—C21a | −144.5 (4) | C9b—C8b—C16b—C17b | 28.8 (6) |
C21a—C16a—C17a—C18a | −0.8 (6) | C21b—C16b—C17b—C18b | −0.1 (5) |
C8a—C16a—C17a—C18a | 179.3 (4) | C8b—C16b—C17b—C18b | −179.9 (3) |
C16a—C17a—C18a—C19a | 0.1 (6) | C16b—C17b—C18b—C19b | 0.2 (6) |
C17a—C18a—C19a—C20a | 0.2 (7) | C17b—C18b—C19b—C20b | −0.6 (7) |
C18a—C19a—C20a—C21a | 0.1 (7) | C18b—C19b—C20b—C21b | 0.9 (6) |
C19a—C20a—C21a—C16a | −0.8 (7) | C19b—C20b—C21b—C16b | −0.9 (6) |
C17a—C16a—C21a—C20a | 1.1 (6) | C17b—C16b—C21b—C20b | 0.5 (5) |
C8a—C16a—C21a—C20a | −179.0 (4) | C8b—C16b—C21b—C20b | −179.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1a—H1a···O3 | 0.86 | 1.96 | 2.819 (4) | 175 |
N1b—H1b···O3bi | 0.86 | 1.95 | 2.788 (4) | 166 |
O3a—H3Oa···N2bi | 0.82 | 1.98 | 2.791 (4) | 171 |
O3b—H3Ob···N2a | 0.82 | 1.98 | 2.792 (4) | 169 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
C22H17N3O2·CH4O | F(000) = 816 |
Mr = 387.43 | Dx = 1.275 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11012 reflections |
a = 5.813 (1) Å | θ = 1.6–25.0° |
b = 15.003 (3) Å | µ = 0.09 mm−1 |
c = 23.243 (5) Å | T = 293 K |
β = 95.480 (3)° | Plate, yellow |
V = 2017.8 (7) Å3 | 0.09 × 0.02 × 0.02 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 1604 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.084 |
Graphite monochromator | θmax = 25.0°, θmin = 1.6° |
ϕ– and ω scans | h = 0→5 |
11012 measured reflections | k = 0→17 |
3292 independent reflections | l = −27→27 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 0.91 | w = 1/[σ2(Fo2) + (0.0753P)2] where P = (Fo2 + 2Fc2)/3 |
3292 reflections | (Δ/σ)max = 0.048 |
263 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C22H17N3O2·CH4O | V = 2017.8 (7) Å3 |
Mr = 387.43 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.813 (1) Å | µ = 0.09 mm−1 |
b = 15.003 (3) Å | T = 293 K |
c = 23.243 (5) Å | 0.09 × 0.02 × 0.02 mm |
β = 95.480 (3)° |
Nonius KappaCCD diffractometer | 1604 reflections with I > 2σ(I) |
11012 measured reflections | Rint = 0.084 |
3292 independent reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 0.91 | Δρmax = 0.15 e Å−3 |
3292 reflections | Δρmin = −0.24 e Å−3 |
263 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.2885 (4) | 0.3380 (2) | 0.52554 (12) | 0.0880 (9) | |
O2 | 0.4324 (5) | 0.2263 (2) | 0.57504 (14) | 0.1111 (11) | |
O33 | 0.2762 (5) | 0.09682 (17) | 0.37431 (13) | 0.0935 (9) | |
H33 | 0.2645 | 0.1494 | 0.3831 | 0.112* | |
N1 | −0.0704 (4) | 0.37648 (18) | 0.42371 (11) | 0.0505 (7) | |
N2 | 0.1675 (4) | 0.27789 (16) | 0.39029 (11) | 0.0512 (7) | |
N3 | 0.2822 (5) | 0.2607 (3) | 0.54190 (14) | 0.0726 (9) | |
C1 | −0.0455 (5) | 0.2257 (2) | 0.47055 (14) | 0.0514 (8) | |
C2 | −0.2336 (6) | 0.1714 (3) | 0.45527 (17) | 0.0791 (12) | |
H2 | −0.3256 | 0.1818 | 0.4193 | 0.095* | |
C3 | −0.2915 (7) | 0.1017 (3) | 0.4896 (2) | 0.0923 (14) | |
H3 | −0.4253 | 0.0660 | 0.4782 | 0.111* | |
C4 | −0.1617 (7) | 0.0836 (3) | 0.5401 (2) | 0.0851 (13) | |
H4 | −0.1995 | 0.0350 | 0.5643 | 0.102* | |
C5 | 0.0280 (6) | 0.1355 (3) | 0.55661 (16) | 0.0725 (11) | |
H5 | 0.1246 | 0.1249 | 0.5918 | 0.087* | |
C6 | 0.0808 (5) | 0.2055 (2) | 0.52228 (14) | 0.0532 (8) | |
C7 | 0.0194 (5) | 0.2935 (2) | 0.42873 (14) | 0.0513 (8) | |
C8 | 0.0305 (5) | 0.41818 (19) | 0.37860 (13) | 0.0441 (7) | |
C9 | 0.1740 (5) | 0.3553 (2) | 0.35840 (13) | 0.0470 (8) | |
C10 | 0.3154 (5) | 0.3597 (2) | 0.30860 (13) | 0.0459 (8) | |
C11 | 0.5046 (5) | 0.3035 (2) | 0.30674 (15) | 0.0567 (9) | |
H11 | 0.5402 | 0.2625 | 0.3380 | 0.068* | |
C12 | 0.6398 (6) | 0.3065 (2) | 0.26103 (17) | 0.0648 (10) | |
H12 | 0.7715 | 0.2680 | 0.2602 | 0.078* | |
C13 | 0.5869 (6) | 0.3646 (3) | 0.21620 (16) | 0.0656 (10) | |
H13 | 0.6812 | 0.3658 | 0.1845 | 0.079* | |
C14 | 0.3998 (6) | 0.4205 (2) | 0.21691 (15) | 0.0641 (9) | |
H14 | 0.3603 | 0.4616 | 0.1859 | 0.077* | |
C15 | 0.2640 (5) | 0.4176 (2) | 0.26310 (14) | 0.0532 (8) | |
H15 | 0.1322 | 0.4561 | 0.2632 | 0.064* | |
C16 | −0.0185 (4) | 0.51185 (19) | 0.36222 (13) | 0.0427 (8) | |
C17 | 0.1498 (5) | 0.5766 (2) | 0.37229 (14) | 0.0525 (8) | |
H17 | 0.2968 | 0.5606 | 0.3919 | 0.063* | |
C18 | 0.1072 (6) | 0.6636 (2) | 0.35467 (16) | 0.0641 (10) | |
H18 | 0.2242 | 0.7084 | 0.3618 | 0.077* | |
C19 | −0.1041 (6) | 0.6866 (2) | 0.32683 (16) | 0.0666 (10) | |
H19 | −0.1337 | 0.7464 | 0.3134 | 0.080* | |
C20 | −0.2734 (6) | 0.6228 (2) | 0.31756 (15) | 0.0656 (10) | |
H20 | −0.4220 | 0.6393 | 0.2990 | 0.079* | |
C21 | −0.2322 (5) | 0.5365 (2) | 0.33454 (15) | 0.0588 (9) | |
H21 | −0.3514 | 0.4924 | 0.3278 | 0.071* | |
C22 | −0.2369 (6) | 0.4160 (2) | 0.45944 (15) | 0.0689 (10) | |
H22A | −0.2129 | 0.4792 | 0.4618 | 0.083* | |
H22B | −0.2164 | 0.3907 | 0.4975 | 0.083* | |
H22C | −0.3909 | 0.4040 | 0.4425 | 0.083* | |
C23 | 0.1106 (10) | 0.0763 (3) | 0.3312 (2) | 0.1234 (18) | |
H23A | 0.1665 | 0.0893 | 0.2945 | 0.148* | |
H23B | −0.0255 | 0.1110 | 0.3354 | 0.148* | |
H23C | 0.0737 | 0.0140 | 0.3330 | 0.148* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0923 (19) | 0.089 (2) | 0.082 (2) | −0.0329 (16) | 0.0030 (14) | 0.0040 (17) |
O2 | 0.0810 (18) | 0.137 (3) | 0.108 (3) | 0.0089 (18) | −0.0287 (17) | 0.003 (2) |
O33 | 0.107 (2) | 0.0584 (19) | 0.111 (2) | 0.0009 (14) | −0.0119 (18) | 0.0022 (16) |
N1 | 0.0515 (15) | 0.0465 (17) | 0.0546 (18) | −0.0032 (12) | 0.0110 (12) | 0.0028 (14) |
N2 | 0.0587 (16) | 0.0405 (17) | 0.0542 (17) | −0.0028 (12) | 0.0045 (13) | 0.0067 (14) |
N3 | 0.068 (2) | 0.090 (3) | 0.059 (2) | −0.0031 (19) | 0.0008 (16) | −0.004 (2) |
C1 | 0.0610 (19) | 0.041 (2) | 0.053 (2) | −0.0065 (15) | 0.0057 (16) | 0.0069 (17) |
C2 | 0.082 (2) | 0.079 (3) | 0.072 (3) | −0.028 (2) | −0.0136 (19) | 0.030 (2) |
C3 | 0.098 (3) | 0.084 (3) | 0.092 (3) | −0.034 (2) | −0.004 (3) | 0.032 (3) |
C4 | 0.103 (3) | 0.061 (3) | 0.093 (4) | −0.012 (2) | 0.019 (3) | 0.027 (2) |
C5 | 0.084 (3) | 0.076 (3) | 0.057 (2) | 0.007 (2) | 0.0047 (19) | 0.022 (2) |
C6 | 0.060 (2) | 0.051 (2) | 0.048 (2) | −0.0035 (15) | 0.0045 (16) | −0.0005 (18) |
C7 | 0.0595 (19) | 0.042 (2) | 0.053 (2) | −0.0063 (15) | 0.0066 (16) | 0.0062 (17) |
C8 | 0.0467 (16) | 0.0372 (18) | 0.049 (2) | −0.0054 (14) | 0.0058 (14) | 0.0059 (16) |
C9 | 0.0487 (17) | 0.039 (2) | 0.052 (2) | −0.0055 (14) | 0.0020 (14) | 0.0054 (17) |
C10 | 0.0504 (17) | 0.0396 (19) | 0.048 (2) | −0.0053 (14) | 0.0040 (14) | 0.0032 (16) |
C11 | 0.059 (2) | 0.048 (2) | 0.063 (2) | −0.0006 (16) | 0.0081 (17) | 0.0007 (18) |
C12 | 0.067 (2) | 0.054 (2) | 0.075 (3) | 0.0027 (17) | 0.015 (2) | −0.007 (2) |
C13 | 0.071 (2) | 0.068 (3) | 0.061 (2) | −0.0107 (19) | 0.0226 (18) | −0.013 (2) |
C14 | 0.078 (2) | 0.065 (2) | 0.050 (2) | −0.0028 (19) | 0.0075 (18) | 0.0039 (19) |
C15 | 0.0559 (19) | 0.054 (2) | 0.049 (2) | −0.0009 (15) | 0.0058 (16) | −0.0005 (18) |
C16 | 0.0436 (17) | 0.0406 (19) | 0.045 (2) | −0.0024 (13) | 0.0093 (13) | 0.0012 (15) |
C17 | 0.0459 (17) | 0.047 (2) | 0.065 (2) | −0.0046 (15) | 0.0054 (14) | 0.0044 (17) |
C18 | 0.063 (2) | 0.044 (2) | 0.087 (3) | −0.0122 (16) | 0.0128 (19) | 0.000 (2) |
C19 | 0.082 (3) | 0.040 (2) | 0.080 (3) | 0.0076 (19) | 0.022 (2) | 0.0101 (19) |
C20 | 0.059 (2) | 0.056 (2) | 0.082 (3) | 0.0072 (18) | 0.0074 (18) | 0.012 (2) |
C21 | 0.0485 (18) | 0.051 (2) | 0.076 (3) | −0.0069 (15) | 0.0017 (16) | 0.0041 (19) |
C22 | 0.072 (2) | 0.065 (3) | 0.073 (3) | 0.0003 (18) | 0.0272 (19) | 0.007 (2) |
C23 | 0.176 (5) | 0.081 (4) | 0.105 (4) | 0.006 (3) | −0.029 (4) | −0.022 (3) |
O1—N3 | 1.223 (4) | C11—C12 | 1.381 (4) |
O2—N3 | 1.222 (4) | C11—H11 | 0.9599 |
O33—C23 | 1.358 (5) | C12—C13 | 1.371 (5) |
O33—H33 | 0.8199 | C12—H12 | 0.9601 |
N1—C7 | 1.350 (4) | C13—C14 | 1.375 (4) |
N1—C8 | 1.397 (4) | C13—H13 | 0.9599 |
N1—C22 | 1.460 (4) | C14—C15 | 1.393 (4) |
N2—C7 | 1.320 (4) | C14—H14 | 0.9600 |
N2—C9 | 1.380 (4) | C15—H15 | 0.9600 |
N3—C6 | 1.471 (4) | C16—C17 | 1.382 (4) |
C1—C6 | 1.381 (4) | C16—C21 | 1.393 (4) |
C1—C2 | 1.383 (4) | C17—C18 | 1.383 (4) |
C1—C7 | 1.481 (4) | C17—H17 | 0.9600 |
C2—C3 | 1.377 (5) | C18—C19 | 1.377 (5) |
C2—H2 | 0.9601 | C18—H18 | 0.9599 |
C3—C4 | 1.360 (5) | C19—C20 | 1.375 (5) |
C3—H3 | 0.9600 | C19—H19 | 0.9600 |
C4—C5 | 1.374 (5) | C20—C21 | 1.369 (4) |
C4—H4 | 0.9600 | C20—H20 | 0.9600 |
C5—C6 | 1.371 (5) | C21—H21 | 0.9599 |
C5—H5 | 0.9598 | C22—H22A | 0.9600 |
C8—C9 | 1.372 (4) | C22—H22B | 0.9600 |
C8—C16 | 1.477 (4) | C22—H22C | 0.9600 |
C9—C10 | 1.484 (4) | C23—H23A | 0.9601 |
C10—C15 | 1.378 (4) | C23—H23B | 0.9600 |
C10—C11 | 1.390 (4) | C23—H23C | 0.9600 |
C23—O33—H33 | 109.5 | C13—C12—H12 | 119.2 |
C7—N1—C8 | 106.9 (2) | C11—C12—H12 | 120.6 |
C7—N1—C22 | 126.6 (3) | C12—C13—C14 | 119.9 (3) |
C8—N1—C22 | 126.4 (3) | C12—C13—H13 | 119.6 |
C7—N2—C9 | 105.5 (2) | C14—C13—H13 | 120.5 |
O2—N3—O1 | 123.8 (3) | C13—C14—C15 | 119.8 (3) |
O2—N3—C6 | 117.2 (4) | C13—C14—H14 | 121.0 |
O1—N3—C6 | 119.0 (3) | C15—C14—H14 | 119.2 |
C6—C1—C2 | 115.8 (3) | C10—C15—C14 | 120.9 (3) |
C6—C1—C7 | 125.1 (3) | C10—C15—H15 | 119.4 |
C2—C1—C7 | 118.7 (3) | C14—C15—H15 | 119.6 |
C3—C2—C1 | 122.0 (4) | C17—C16—C21 | 118.5 (3) |
C3—C2—H2 | 118.7 | C17—C16—C8 | 120.6 (3) |
C1—C2—H2 | 119.3 | C21—C16—C8 | 120.8 (3) |
C4—C3—C2 | 120.3 (4) | C16—C17—C18 | 120.6 (3) |
C4—C3—H3 | 119.7 | C16—C17—H17 | 119.3 |
C2—C3—H3 | 120.0 | C18—C17—H17 | 120.1 |
C3—C4—C5 | 119.5 (4) | C19—C18—C17 | 120.2 (3) |
C3—C4—H4 | 121.2 | C19—C18—H18 | 119.4 |
C5—C4—H4 | 119.3 | C17—C18—H18 | 120.5 |
C6—C5—C4 | 119.3 (4) | C20—C19—C18 | 119.5 (3) |
C6—C5—H5 | 118.5 | C20—C19—H19 | 119.8 |
C4—C5—H5 | 122.2 | C18—C19—H19 | 120.8 |
C5—C6—C1 | 123.0 (3) | C21—C20—C19 | 120.7 (3) |
C5—C6—N3 | 117.8 (3) | C21—C20—H20 | 119.9 |
C1—C6—N3 | 119.2 (3) | C19—C20—H20 | 119.4 |
N2—C7—N1 | 112.2 (3) | C20—C21—C16 | 120.5 (3) |
N2—C7—C1 | 123.1 (3) | C20—C21—H21 | 120.1 |
N1—C7—C1 | 124.7 (3) | C16—C21—H21 | 119.4 |
C9—C8—N1 | 105.2 (3) | N1—C22—H22A | 109.5 |
C9—C8—C16 | 132.4 (3) | N1—C22—H22B | 109.5 |
N1—C8—C16 | 122.4 (3) | H22A—C22—H22B | 109.5 |
C8—C9—N2 | 110.3 (3) | N1—C22—H22C | 109.5 |
C8—C9—C10 | 129.5 (3) | H22A—C22—H22C | 109.5 |
N2—C9—C10 | 120.2 (3) | H22B—C22—H22C | 109.5 |
C15—C10—C11 | 118.2 (3) | O33—C23—H23A | 109.5 |
C15—C10—C9 | 122.1 (3) | O33—C23—H23B | 109.4 |
C11—C10—C9 | 119.7 (3) | H23A—C23—H23B | 109.5 |
C12—C11—C10 | 120.9 (3) | O33—C23—H23C | 109.5 |
C12—C11—H11 | 120.4 | H23A—C23—H23C | 109.5 |
C10—C11—H11 | 118.7 | H23B—C23—H23C | 109.5 |
C13—C12—C11 | 120.2 (3) | ||
C6—C1—C2—C3 | 0.1 (6) | C16—C8—C9—N2 | 176.8 (3) |
C7—C1—C2—C3 | 174.0 (4) | N1—C8—C9—C10 | 175.9 (3) |
C1—C2—C3—C4 | −0.6 (7) | C16—C8—C9—C10 | −6.0 (5) |
C2—C3—C4—C5 | 0.0 (7) | C7—N2—C9—C8 | 0.8 (3) |
C3—C4—C5—C6 | 1.0 (6) | C7—N2—C9—C10 | −176.7 (3) |
C4—C5—C6—C1 | −1.5 (6) | C8—C9—C10—C15 | −22.7 (5) |
C4—C5—C6—N3 | 178.8 (3) | N2—C9—C10—C15 | 154.2 (3) |
C2—C1—C6—C5 | 0.9 (5) | C8—C9—C10—C11 | 158.1 (3) |
C7—C1—C6—C5 | −172.5 (3) | N2—C9—C10—C11 | −25.0 (4) |
C2—C1—C6—N3 | −179.4 (3) | C15—C10—C11—C12 | 1.1 (4) |
C7—C1—C6—N3 | 7.3 (5) | C9—C10—C11—C12 | −179.7 (3) |
O2—N3—C6—C5 | 24.2 (5) | C10—C11—C12—C13 | −0.8 (5) |
O1—N3—C6—C5 | −154.2 (3) | C11—C12—C13—C14 | 0.4 (5) |
O2—N3—C6—C1 | −155.5 (3) | C12—C13—C14—C15 | −0.3 (5) |
O1—N3—C6—C1 | 26.1 (5) | C11—C10—C15—C14 | −0.9 (5) |
C9—N2—C7—N1 | 0.0 (3) | C9—C10—C15—C14 | 179.9 (3) |
C9—N2—C7—C1 | 177.6 (3) | C13—C14—C15—C10 | 0.5 (5) |
C8—N1—C7—N2 | −0.7 (4) | C9—C8—C16—C17 | −67.2 (5) |
C22—N1—C7—N2 | −179.4 (3) | N1—C8—C16—C17 | 110.6 (3) |
C8—N1—C7—C1 | −178.3 (3) | C9—C8—C16—C21 | 110.6 (4) |
C22—N1—C7—C1 | 3.0 (5) | N1—C8—C16—C21 | −71.6 (4) |
C6—C1—C7—N2 | 82.4 (4) | C21—C16—C17—C18 | −0.7 (5) |
C2—C1—C7—N2 | −90.8 (4) | C8—C16—C17—C18 | 177.1 (3) |
C6—C1—C7—N1 | −100.2 (4) | C16—C17—C18—C19 | 0.0 (5) |
C2—C1—C7—N1 | 86.6 (4) | C17—C18—C19—C20 | 1.1 (5) |
C7—N1—C8—C9 | 1.2 (3) | C18—C19—C20—C21 | −1.5 (5) |
C22—N1—C8—C9 | 179.8 (3) | C19—C20—C21—C16 | 0.8 (5) |
C7—N1—C8—C16 | −177.1 (3) | C17—C16—C21—C20 | 0.3 (5) |
C22—N1—C8—C16 | 1.5 (4) | C8—C16—C21—C20 | −177.6 (3) |
N1—C8—C9—N2 | −1.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···O2i | 0.96 | 2.56 | 3.426 (4) | 150 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
C22H17N3O2 | F(000) = 744 |
Mr = 355.39 | Dx = 1.310 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 10123 reflections |
a = 16.242 (3) Å | θ = 1.3–25.1° |
b = 9.583 (2) Å | µ = 0.09 mm−1 |
c = 11.615 (2) Å | T = 293 K |
β = 94.36 (2)° | Plate, yellow |
V = 1802.6 (6) Å3 | 0.08 × 0.03 × 0.01 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 1975 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.055 |
Graphite monochromator | θmax = 25.1°, θmin = 1.3° |
ϕ– and ω scans | h = −19→19 |
10123 measured reflections | k = −11→0 |
3139 independent reflections | l = 0→13 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0845P)2] where P = (Fo2 + 2Fc2)/3 |
3139 reflections | (Δ/σ)max < 0.001 |
244 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C22H17N3O2 | V = 1802.6 (6) Å3 |
Mr = 355.39 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.242 (3) Å | µ = 0.09 mm−1 |
b = 9.583 (2) Å | T = 293 K |
c = 11.615 (2) Å | 0.08 × 0.03 × 0.01 mm |
β = 94.36 (2)° |
Nonius KappaCCD diffractometer | 1975 reflections with I > 2σ(I) |
10123 measured reflections | Rint = 0.055 |
3139 independent reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.26 e Å−3 |
3139 reflections | Δρmin = −0.21 e Å−3 |
244 parameters |
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 | 0.29718 (11) | 0.62150 (18) | 0.56097 (15) | 0.0500 (5) | |
N2 | 0.24985 (12) | 0.77893 (17) | 0.43241 (16) | 0.0494 (5) | |
N3 | 0.44693 (14) | 1.1969 (2) | 0.4849 (2) | 0.0663 (6) | |
O1 | 0.43516 (13) | 1.18055 (19) | 0.38129 (19) | 0.0843 (6) | |
O2 | 0.48089 (15) | 1.2993 (2) | 0.5286 (2) | 0.1030 (8) | |
C1 | 0.35062 (14) | 0.8685 (2) | 0.58039 (18) | 0.0464 (6) | |
C2 | 0.36471 (16) | 0.8822 (2) | 0.7004 (2) | 0.0575 (7) | |
H2 | 0.3456 | 0.8110 | 0.7500 | 0.069* | |
C3 | 0.40664 (17) | 0.9967 (3) | 0.7481 (2) | 0.0640 (7) | |
H3 | 0.4157 | 1.0067 | 0.8304 | 0.077* | |
C4 | 0.43443 (16) | 1.1010 (2) | 0.6788 (2) | 0.0612 (7) | |
H4 | 0.4644 | 1.1810 | 0.7090 | 0.073* | |
C5 | 0.41943 (14) | 1.0863 (2) | 0.5615 (2) | 0.0518 (6) | |
C6 | 0.37952 (14) | 0.9729 (2) | 0.5113 (2) | 0.0490 (6) | |
H6 | 0.3712 | 0.9639 | 0.4289 | 0.059* | |
C7 | 0.30113 (14) | 0.7572 (2) | 0.52405 (19) | 0.0471 (6) | |
C8 | 0.23869 (14) | 0.5544 (2) | 0.48800 (19) | 0.0477 (6) | |
C9 | 0.20959 (14) | 0.6538 (2) | 0.40956 (18) | 0.0454 (6) | |
C10 | 0.14388 (14) | 0.6451 (2) | 0.31503 (19) | 0.0474 (6) | |
C11 | 0.08058 (16) | 0.5466 (2) | 0.3139 (2) | 0.0626 (7) | |
H11 | 0.0797 | 0.4805 | 0.3758 | 0.075* | |
C12 | 0.01967 (18) | 0.5451 (3) | 0.2239 (3) | 0.0766 (8) | |
H12 | −0.0239 | 0.4775 | 0.2237 | 0.092* | |
C13 | 0.02078 (18) | 0.6384 (3) | 0.1349 (2) | 0.0736 (8) | |
H13 | −0.0221 | 0.6364 | 0.0734 | 0.088* | |
C14 | 0.08184 (17) | 0.7361 (3) | 0.1353 (2) | 0.0701 (8) | |
H14 | 0.0839 | 0.8002 | 0.0720 | 0.084* | |
C15 | 0.14259 (16) | 0.7400 (2) | 0.2247 (2) | 0.0587 (7) | |
H15 | 0.1846 | 0.8105 | 0.2256 | 0.070* | |
C16 | 0.21831 (15) | 0.4063 (2) | 0.5027 (2) | 0.0514 (6) | |
C17 | 0.18107 (19) | 0.3616 (3) | 0.5993 (2) | 0.0752 (8) | |
H17 | 0.1683 | 0.4293 | 0.6561 | 0.090* | |
C18 | 0.1625 (2) | 0.2221 (3) | 0.6144 (3) | 0.0921 (11) | |
H18 | 0.1368 | 0.1893 | 0.6810 | 0.111* | |
C19 | 0.1812 (2) | 0.1270 (3) | 0.5320 (3) | 0.0830 (10) | |
H19 | 0.1690 | 0.0302 | 0.5438 | 0.100* | |
C20 | 0.21659 (18) | 0.1693 (3) | 0.4354 (3) | 0.0764 (9) | |
H20 | 0.2277 | 0.1009 | 0.3783 | 0.092* | |
C21 | 0.23568 (16) | 0.3083 (2) | 0.4202 (2) | 0.0634 (7) | |
H21 | 0.2617 | 0.3385 | 0.3530 | 0.076* | |
C22 | 0.35172 (17) | 0.5524 (2) | 0.6496 (2) | 0.0691 (8) | |
H22A | 0.3354 | 0.4571 | 0.6593 | 0.083* | |
H22B | 0.3491 | 0.6015 | 0.7212 | 0.083* | |
H22C | 0.4072 | 0.5552 | 0.6264 | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0561 (13) | 0.0501 (11) | 0.0426 (11) | −0.0010 (9) | −0.0033 (9) | 0.0017 (9) |
N2 | 0.0557 (12) | 0.0462 (11) | 0.0458 (12) | −0.0036 (9) | −0.0001 (10) | 0.0020 (8) |
N3 | 0.0671 (15) | 0.0512 (13) | 0.0816 (18) | −0.0004 (10) | 0.0123 (13) | 0.0005 (12) |
O1 | 0.1007 (17) | 0.0839 (13) | 0.0682 (14) | −0.0091 (11) | 0.0065 (12) | 0.0221 (11) |
O2 | 0.131 (2) | 0.0606 (11) | 0.1202 (19) | −0.0323 (12) | 0.0265 (15) | −0.0146 (12) |
C1 | 0.0493 (14) | 0.0505 (13) | 0.0388 (13) | 0.0007 (10) | 0.0006 (11) | −0.0042 (10) |
C2 | 0.0649 (17) | 0.0610 (14) | 0.0470 (14) | −0.0037 (12) | 0.0061 (12) | 0.0001 (12) |
C3 | 0.0714 (19) | 0.0762 (17) | 0.0437 (14) | −0.0067 (14) | 0.0003 (13) | −0.0116 (13) |
C4 | 0.0611 (17) | 0.0588 (15) | 0.0630 (17) | −0.0053 (12) | −0.0008 (13) | −0.0139 (13) |
C5 | 0.0537 (16) | 0.0474 (13) | 0.0541 (15) | −0.0001 (11) | 0.0034 (12) | −0.0016 (12) |
C6 | 0.0513 (15) | 0.0544 (14) | 0.0411 (13) | 0.0034 (11) | 0.0023 (11) | −0.0023 (11) |
C7 | 0.0504 (15) | 0.0487 (13) | 0.0417 (13) | −0.0019 (10) | 0.0006 (11) | 0.0004 (10) |
C8 | 0.0518 (15) | 0.0491 (13) | 0.0422 (13) | −0.0004 (10) | 0.0036 (11) | −0.0035 (11) |
C9 | 0.0516 (15) | 0.0442 (13) | 0.0411 (13) | −0.0011 (10) | 0.0067 (11) | −0.0023 (10) |
C10 | 0.0471 (15) | 0.0491 (13) | 0.0457 (13) | 0.0022 (10) | 0.0028 (11) | −0.0066 (11) |
C11 | 0.0621 (18) | 0.0614 (15) | 0.0633 (17) | −0.0084 (13) | −0.0024 (14) | 0.0029 (12) |
C12 | 0.0575 (19) | 0.0809 (19) | 0.089 (2) | −0.0115 (14) | −0.0101 (17) | −0.0015 (17) |
C13 | 0.0602 (18) | 0.097 (2) | 0.0610 (18) | 0.0052 (16) | −0.0138 (15) | −0.0042 (16) |
C14 | 0.0625 (18) | 0.0881 (18) | 0.0586 (17) | 0.0040 (15) | −0.0016 (14) | 0.0135 (14) |
C15 | 0.0580 (17) | 0.0649 (15) | 0.0521 (15) | −0.0020 (12) | −0.0029 (13) | 0.0091 (12) |
C16 | 0.0570 (15) | 0.0454 (13) | 0.0506 (15) | 0.0024 (11) | −0.0034 (12) | 0.0048 (12) |
C17 | 0.108 (2) | 0.0593 (17) | 0.0589 (17) | −0.0147 (15) | 0.0092 (16) | 0.0024 (13) |
C18 | 0.119 (3) | 0.075 (2) | 0.079 (2) | −0.0299 (19) | −0.009 (2) | 0.0268 (18) |
C19 | 0.080 (2) | 0.0496 (16) | 0.113 (3) | −0.0068 (14) | −0.036 (2) | 0.0140 (19) |
C20 | 0.069 (2) | 0.0544 (17) | 0.103 (3) | 0.0041 (13) | −0.0100 (19) | −0.0133 (16) |
C21 | 0.0598 (17) | 0.0566 (15) | 0.0736 (18) | 0.0024 (12) | 0.0040 (14) | −0.0080 (14) |
C22 | 0.0704 (19) | 0.0623 (15) | 0.0705 (18) | 0.0042 (12) | −0.0221 (15) | 0.0087 (12) |
N1—C7 | 1.372 (3) | C11—C12 | 1.384 (4) |
N1—C8 | 1.383 (3) | C11—H11 | 0.9600 |
N1—C22 | 1.464 (3) | C12—C13 | 1.367 (4) |
N2—C7 | 1.317 (3) | C12—H12 | 0.9599 |
N2—C9 | 1.382 (3) | C13—C14 | 1.364 (4) |
N3—O1 | 1.214 (3) | C13—H13 | 0.9601 |
N3—O2 | 1.217 (3) | C14—C15 | 1.378 (3) |
N3—C5 | 1.475 (3) | C14—H14 | 0.9600 |
C1—C6 | 1.387 (3) | C15—H15 | 0.9600 |
C1—C2 | 1.401 (3) | C16—C17 | 1.382 (4) |
C1—C7 | 1.460 (3) | C16—C21 | 1.386 (3) |
C2—C3 | 1.385 (3) | C17—C18 | 1.384 (4) |
C2—H2 | 0.9600 | C17—H17 | 0.9599 |
C3—C4 | 1.381 (4) | C18—C19 | 1.372 (4) |
C3—H3 | 0.9600 | C18—H18 | 0.9599 |
C4—C5 | 1.373 (3) | C19—C20 | 1.361 (4) |
C4—H4 | 0.9599 | C19—H19 | 0.9599 |
C5—C6 | 1.372 (3) | C20—C21 | 1.382 (4) |
C6—H6 | 0.9599 | C20—H20 | 0.9601 |
C8—C9 | 1.377 (3) | C21—H21 | 0.9600 |
C8—C16 | 1.470 (3) | C22—H22A | 0.9600 |
C9—C10 | 1.474 (3) | C22—H22B | 0.9599 |
C10—C15 | 1.387 (3) | C22—H22C | 0.9600 |
C10—C11 | 1.395 (3) | ||
C7—N1—C8 | 107.19 (17) | C12—C11—H11 | 120.6 |
C7—N1—C22 | 127.45 (18) | C10—C11—H11 | 119.5 |
C8—N1—C22 | 124.83 (18) | C13—C12—C11 | 121.0 (3) |
C7—N2—C9 | 106.20 (17) | C13—C12—H12 | 119.4 |
O1—N3—O2 | 123.3 (2) | C11—C12—H12 | 119.6 |
O1—N3—C5 | 118.2 (2) | C14—C13—C12 | 119.9 (2) |
O2—N3—C5 | 118.4 (2) | C14—C13—H13 | 120.2 |
C6—C1—C2 | 118.1 (2) | C12—C13—H13 | 120.0 |
C6—C1—C7 | 117.8 (2) | C13—C14—C15 | 120.0 (3) |
C2—C1—C7 | 123.8 (2) | C13—C14—H14 | 120.3 |
C3—C2—C1 | 120.7 (2) | C15—C14—H14 | 119.7 |
C3—C2—H2 | 119.7 | C14—C15—C10 | 121.4 (2) |
C1—C2—H2 | 119.6 | C14—C15—H15 | 119.6 |
C4—C3—C2 | 120.8 (2) | C10—C15—H15 | 118.9 |
C4—C3—H3 | 118.4 | C17—C16—C21 | 118.4 (2) |
C2—C3—H3 | 120.7 | C17—C16—C8 | 120.6 (2) |
C5—C4—C3 | 117.6 (2) | C21—C16—C8 | 121.0 (2) |
C5—C4—H4 | 119.4 | C16—C17—C18 | 121.0 (3) |
C3—C4—H4 | 122.9 | C16—C17—H17 | 118.7 |
C6—C5—C4 | 123.1 (2) | C18—C17—H17 | 120.3 |
C6—C5—N3 | 117.9 (2) | C19—C18—C17 | 119.4 (3) |
C4—C5—N3 | 119.1 (2) | C19—C18—H18 | 118.5 |
C5—C6—C1 | 119.7 (2) | C17—C18—H18 | 122.1 |
C5—C6—H6 | 121.4 | C20—C19—C18 | 120.4 (3) |
C1—C6—H6 | 118.9 | C20—C19—H19 | 120.7 |
N2—C7—N1 | 111.14 (18) | C18—C19—H19 | 118.9 |
N2—C7—C1 | 122.63 (19) | C19—C20—C21 | 120.4 (3) |
N1—C7—C1 | 126.12 (19) | C19—C20—H20 | 118.7 |
C9—C8—N1 | 105.59 (18) | C21—C20—H20 | 120.9 |
C9—C8—C16 | 132.52 (19) | C20—C21—C16 | 120.3 (3) |
N1—C8—C16 | 121.89 (18) | C20—C21—H21 | 120.8 |
C8—C9—N2 | 109.87 (18) | C16—C21—H21 | 118.9 |
C8—C9—C10 | 130.25 (19) | N1—C22—H22A | 110.8 |
N2—C9—C10 | 119.84 (18) | N1—C22—H22B | 108.9 |
C15—C10—C11 | 117.9 (2) | H22A—C22—H22B | 109.5 |
C15—C10—C9 | 119.6 (2) | N1—C22—H22C | 108.7 |
C11—C10—C9 | 122.5 (2) | H22A—C22—H22C | 109.5 |
C12—C11—C10 | 119.9 (2) | H22B—C22—H22C | 109.5 |
C6—C1—C2—C3 | −0.2 (4) | C16—C8—C9—N2 | −179.4 (2) |
C7—C1—C2—C3 | −174.7 (2) | N1—C8—C9—C10 | −176.6 (2) |
C1—C2—C3—C4 | 1.0 (4) | C16—C8—C9—C10 | 3.1 (4) |
C2—C3—C4—C5 | −0.4 (4) | C7—N2—C9—C8 | −1.2 (3) |
C3—C4—C5—C6 | −0.9 (4) | C7—N2—C9—C10 | 176.5 (2) |
C3—C4—C5—N3 | 178.9 (2) | C8—C9—C10—C15 | −159.0 (2) |
O1—N3—C5—C6 | −2.1 (3) | N2—C9—C10—C15 | 23.8 (3) |
O2—N3—C5—C6 | 178.5 (2) | C8—C9—C10—C11 | 22.9 (4) |
O1—N3—C5—C4 | 178.1 (2) | N2—C9—C10—C11 | −154.3 (2) |
O2—N3—C5—C4 | −1.3 (3) | C15—C10—C11—C12 | 0.6 (4) |
C4—C5—C6—C1 | 1.6 (4) | C9—C10—C11—C12 | 178.8 (2) |
N3—C5—C6—C1 | −178.2 (2) | C10—C11—C12—C13 | 0.5 (4) |
C2—C1—C6—C5 | −1.0 (3) | C11—C12—C13—C14 | −1.1 (4) |
C7—C1—C6—C5 | 173.8 (2) | C12—C13—C14—C15 | 0.5 (4) |
C9—N2—C7—N1 | 1.2 (3) | C13—C14—C15—C10 | 0.7 (4) |
C9—N2—C7—C1 | −175.2 (2) | C11—C10—C15—C14 | −1.2 (4) |
C8—N1—C7—N2 | −0.7 (3) | C9—C10—C15—C14 | −179.4 (2) |
C22—N1—C7—N2 | 171.2 (2) | C9—C8—C16—C17 | −114.0 (3) |
C8—N1—C7—C1 | 175.6 (2) | N1—C8—C16—C17 | 65.8 (3) |
C22—N1—C7—C1 | −12.6 (4) | C9—C8—C16—C21 | 65.8 (4) |
C6—C1—C7—N2 | −34.7 (3) | N1—C8—C16—C21 | −114.4 (3) |
C2—C1—C7—N2 | 139.8 (2) | C21—C16—C17—C18 | 0.9 (4) |
C6—C1—C7—N1 | 149.5 (2) | C8—C16—C17—C18 | −179.3 (2) |
C2—C1—C7—N1 | −36.1 (4) | C16—C17—C18—C19 | −0.2 (4) |
C7—N1—C8—C9 | −0.1 (2) | C17—C18—C19—C20 | −0.9 (5) |
C22—N1—C8—C9 | −172.2 (2) | C18—C19—C20—C21 | 1.3 (4) |
C7—N1—C8—C16 | −179.9 (2) | C19—C20—C21—C16 | −0.5 (4) |
C22—N1—C8—C16 | 8.0 (4) | C17—C16—C21—C20 | −0.5 (4) |
N1—C8—C9—N2 | 0.8 (3) | C8—C16—C21—C20 | 179.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O1i | 0.96 | 2.48 | 3.148 (3) | 127 |
Symmetry code: (i) x, −y+5/2, z+1/2. |
C22H17N3O2 | Z = 4 |
Mr = 355.39 | F(000) = 744 |
Triclinic, P1 | Dx = 1.320 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.855 (2) Å | Cell parameters from 14497 reflections |
b = 12.384 (2) Å | θ = 2.1–26.7° |
c = 14.791 (3) Å | µ = 0.09 mm−1 |
α = 111.95 (3)° | T = 293 K |
β = 99.56 (3)° | Prism, yellow |
γ = 109.63 (3)° | 0.50 × 0.05 × 0.05 mm |
V = 1788.2 (10) Å3 |
Nonius KappaCCD diffractometer | 4081 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.091 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ϕ and ω scans | h = 0→14 |
14497 measured reflections | k = −14→13 |
6250 independent reflections | l = −17→17 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 0.89 | w = 1/[σ2(Fo2) + (0.0865P)2] where P = (Fo2 + 2Fc2)/3 |
6248 reflections | (Δ/σ)max < 0.001 |
489 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C22H17N3O2 | γ = 109.63 (3)° |
Mr = 355.39 | V = 1788.2 (10) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.855 (2) Å | Mo Kα radiation |
b = 12.384 (2) Å | µ = 0.09 mm−1 |
c = 14.791 (3) Å | T = 293 K |
α = 111.95 (3)° | 0.50 × 0.05 × 0.05 mm |
β = 99.56 (3)° |
Nonius KappaCCD diffractometer | 4081 reflections with I > 2σ(I) |
14497 measured reflections | Rint = 0.091 |
6250 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 0.89 | Δρmax = 0.16 e Å−3 |
6248 reflections | Δρmin = −0.19 e Å−3 |
489 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | ||
O1A | 0.62167 (16) | 0.94566 (16) | 0.69731 (11) | 0.0669 (4) | |
O2A | 0.59949 (15) | 1.03422 (16) | 0.59954 (11) | 0.0643 (4) | |
N1A | 0.85884 (13) | 0.57836 (15) | 0.34194 (11) | 0.0410 (4) | |
N2A | 0.70651 (14) | 0.57110 (15) | 0.22603 (11) | 0.0429 (4) | |
N3A | 0.62593 (14) | 0.95609 (15) | 0.61876 (11) | 0.0445 (4) | |
C1A | 0.73778 (16) | 0.70946 (17) | 0.40577 (13) | 0.0386 (4) | |
C2A | 0.68118 (17) | 0.78033 (18) | 0.37790 (13) | 0.0423 (4) | |
H2A | 0.6671 | 0.7727 | 0.3095 | 0.051* | |
C3A | 0.64459 (17) | 0.86116 (18) | 0.44639 (13) | 0.0421 (4) | |
H3A | 0.6062 | 0.9105 | 0.4282 | 0.051* | |
C4A | 0.66476 (16) | 0.87126 (17) | 0.54479 (12) | 0.0387 (4) | |
C5A | 0.72008 (18) | 0.80324 (19) | 0.57544 (13) | 0.0455 (5) | |
H5A | 0.7337 | 0.8130 | 0.6444 | 0.055* | |
C6A | 0.75653 (19) | 0.72307 (19) | 0.50591 (14) | 0.0472 (5) | |
H6A | 0.7955 | 0.6755 | 0.5264 | 0.057* | |
C7A | 0.76783 (16) | 0.62080 (17) | 0.32623 (13) | 0.0398 (4) | |
C8A | 0.85512 (16) | 0.49840 (18) | 0.24490 (13) | 0.0409 (4) | |
C9A | 0.76005 (16) | 0.49490 (18) | 0.17504 (13) | 0.0408 (4) | |
C10A | 0.71068 (17) | 0.42251 (18) | 0.06087 (13) | 0.0426 (4) | |
C11A | 0.71765 (19) | 0.3076 (2) | 0.00647 (15) | 0.0539 (5) | |
H11A | 0.7571 | 0.2734 | 0.0437 | 0.065* | |
C12A | 0.6692 (2) | 0.2419 (2) | −0.10071 (16) | 0.0643 (6) | |
H12A | 0.6761 | 0.1632 | −0.1370 | 0.077* | |
C13A | 0.6102 (2) | 0.2886 (3) | −0.15481 (16) | 0.0691 (7) | |
H13A | 0.5766 | 0.2431 | −0.2290 | 0.083* | |
C14A | 0.6006 (2) | 0.4011 (2) | −0.10233 (15) | 0.0654 (6) | |
H14A | 0.5595 | 0.4344 | −0.1393 | 0.078* | |
C15A | 0.65086 (19) | 0.4683 (2) | 0.00475 (14) | 0.0532 (5) | |
H15A | 0.6430 | 0.5465 | 0.0408 | 0.064* | |
C16A | 0.94456 (17) | 0.43948 (19) | 0.22948 (14) | 0.0467 (5) | |
C17A | 0.95771 (19) | 0.3611 (2) | 0.27347 (17) | 0.0603 (6) | |
H17A | 0.9100 | 0.3479 | 0.3180 | 0.072* | |
C18A | 1.0370 (3) | 0.3016 (3) | 0.2537 (2) | 0.0867 (9) | |
H18A | 1.0454 | 0.2493 | 0.2863 | 0.104* | |
C19A | 1.1043 (3) | 0.3195 (3) | 0.1898 (3) | 0.0984 (11) | |
H19A | 1.1554 | 0.2735 | 0.1755 | 0.118* | |
C20A | 1.0947 (2) | 0.3985 (3) | 0.1463 (2) | 0.0892 (9) | |
H20A | 1.1446 | 0.4120 | 0.1033 | 0.107* | |
C21A | 1.0151 (2) | 0.4588 (2) | 0.16582 (17) | 0.0644 (6) | |
H21A | 1.0070 | 0.5133 | 0.1355 | 0.077* | |
C22A | 0.95606 (18) | 0.6224 (2) | 0.43956 (14) | 0.0566 (6) | |
H22A | 0.9786 | 0.7114 | 0.4843 | 0.068* | |
H22B | 1.0299 | 0.6140 | 0.4260 | 0.068* | |
H22C | 0.9234 | 0.5708 | 0.4723 | 0.068* | |
O1B | 0.60201 (18) | 0.55568 (17) | 0.60989 (12) | 0.0793 (5) | |
O2B | 0.59878 (16) | 0.44631 (16) | 0.69425 (12) | 0.0727 (5) | |
N1B | 0.68974 (13) | 0.07110 (14) | 0.21385 (10) | 0.0388 (4) | |
N2B | 0.82065 (14) | 0.08117 (15) | 0.34619 (10) | 0.0418 (4) | |
N3B | 0.61307 (15) | 0.46610 (17) | 0.62150 (12) | 0.0508 (4) | |
C1B | 0.70423 (16) | 0.21269 (17) | 0.39443 (13) | 0.0379 (4) | |
C2B | 0.67065 (18) | 0.30358 (18) | 0.37796 (14) | 0.0451 (5) | |
H2B | 0.6683 | 0.3085 | 0.3145 | 0.054* | |
C3B | 0.64123 (18) | 0.38684 (19) | 0.45237 (14) | 0.0465 (5) | |
H3B | 0.6169 | 0.4476 | 0.4393 | 0.056* | |
C4B | 0.64727 (16) | 0.37980 (18) | 0.54354 (13) | 0.0402 (4) | |
C5B | 0.68125 (17) | 0.29272 (19) | 0.56329 (13) | 0.0443 (5) | |
H5B | 0.6856 | 0.2894 | 0.6276 | 0.053* | |
C6B | 0.70952 (17) | 0.21002 (18) | 0.48863 (13) | 0.0422 (4) | |
H6B | 0.7344 | 0.1498 | 0.5021 | 0.051* | |
C7B | 0.73725 (16) | 0.12227 (18) | 0.31916 (12) | 0.0381 (4) | |
C8B | 0.74718 (16) | −0.00671 (17) | 0.17279 (12) | 0.0381 (4) | |
C9B | 0.82804 (16) | 0.00061 (18) | 0.25551 (12) | 0.0393 (4) | |
C10B | 0.91252 (17) | −0.06312 (18) | 0.25763 (13) | 0.0426 (5) | |
C11B | 0.9414 (2) | −0.1261 (2) | 0.17135 (16) | 0.0677 (7) | |
H11B | 0.9072 | −0.1262 | 0.1077 | 0.081* | |
C12B | 1.0199 (2) | −0.1873 (3) | 0.1764 (2) | 0.0817 (8) | |
H12B | 1.0390 | −0.2294 | 0.1159 | 0.098* | |
C13B | 1.0707 (2) | −0.1862 (2) | 0.2673 (2) | 0.0686 (7) | |
H13B | 1.1228 | −0.2304 | 0.2706 | 0.082* | |
C14B | 1.04414 (19) | −0.1236 (2) | 0.35344 (18) | 0.0600 (6) | |
H14B | 1.0806 | −0.1209 | 0.4177 | 0.072* | |
C15B | 0.96599 (17) | −0.0632 (2) | 0.34841 (15) | 0.0498 (5) | |
H15B | 0.9490 | −0.0194 | 0.4096 | 0.060* | |
C16B | 0.71506 (17) | −0.07747 (18) | 0.05848 (13) | 0.0389 (4) | |
C17B | 0.76997 (19) | −0.0133 (2) | 0.00666 (14) | 0.0510 (5) | |
H17B | 0.8305 | 0.0760 | 0.0448 | 0.061* | |
C18B | 0.7374 (2) | −0.0775 (2) | −0.09958 (15) | 0.0586 (6) | |
H18B | 0.7758 | −0.0327 | −0.1352 | 0.070* | |
C19B | 0.6497 (2) | −0.2045 (2) | −0.15436 (15) | 0.0573 (6) | |
H19B | 0.6265 | −0.2483 | −0.2283 | 0.069* | |
C20B | 0.5952 (2) | −0.2689 (2) | −0.10402 (15) | 0.0574 (6) | |
H20B | 0.5348 | −0.3582 | −0.1426 | 0.069* | |
C21B | 0.62762 (19) | −0.20544 (19) | 0.00266 (14) | 0.0511 (5) | |
H21B | 0.5890 | −0.2503 | 0.0382 | 0.061* | |
C22B | 0.58548 (19) | 0.0805 (2) | 0.15301 (14) | 0.0544 (6) | |
H22D | 0.5398 | 0.0024 | 0.0888 | 0.065* | |
H22E | 0.6196 | 0.1526 | 0.1392 | 0.065* | |
H22F | 0.5289 | 0.0929 | 0.1912 | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.1028 (12) | 0.0759 (11) | 0.0456 (8) | 0.0535 (10) | 0.0431 (8) | 0.0306 (8) |
O2A | 0.0919 (11) | 0.0681 (11) | 0.0575 (9) | 0.0581 (9) | 0.0335 (8) | 0.0290 (8) |
N1A | 0.0386 (8) | 0.0424 (9) | 0.0353 (8) | 0.0204 (7) | 0.0090 (6) | 0.0105 (7) |
N2A | 0.0450 (8) | 0.0437 (9) | 0.0366 (8) | 0.0247 (7) | 0.0138 (7) | 0.0103 (7) |
N3A | 0.0500 (9) | 0.0410 (10) | 0.0378 (9) | 0.0209 (8) | 0.0164 (7) | 0.0120 (7) |
C1A | 0.0376 (9) | 0.0334 (10) | 0.0360 (9) | 0.0142 (8) | 0.0116 (8) | 0.0089 (8) |
C2A | 0.0455 (10) | 0.0467 (12) | 0.0314 (9) | 0.0224 (9) | 0.0115 (8) | 0.0133 (8) |
C3A | 0.0435 (10) | 0.0429 (11) | 0.0373 (10) | 0.0222 (9) | 0.0113 (8) | 0.0140 (8) |
C4A | 0.0410 (10) | 0.0348 (10) | 0.0351 (9) | 0.0166 (8) | 0.0157 (8) | 0.0097 (8) |
C5A | 0.0602 (12) | 0.0464 (12) | 0.0350 (9) | 0.0275 (10) | 0.0196 (9) | 0.0185 (9) |
C6A | 0.0609 (12) | 0.0461 (12) | 0.0434 (10) | 0.0310 (10) | 0.0205 (9) | 0.0213 (9) |
C7A | 0.0405 (10) | 0.0379 (11) | 0.0369 (10) | 0.0189 (8) | 0.0124 (8) | 0.0117 (8) |
C8A | 0.0396 (10) | 0.0387 (11) | 0.0391 (10) | 0.0182 (8) | 0.0147 (8) | 0.0109 (8) |
C9A | 0.0440 (10) | 0.0403 (11) | 0.0365 (10) | 0.0224 (9) | 0.0164 (8) | 0.0116 (8) |
C10A | 0.0465 (10) | 0.0436 (11) | 0.0360 (9) | 0.0241 (9) | 0.0161 (8) | 0.0117 (8) |
C11A | 0.0584 (12) | 0.0558 (13) | 0.0442 (11) | 0.0329 (11) | 0.0151 (9) | 0.0136 (10) |
C12A | 0.0752 (15) | 0.0594 (15) | 0.0456 (12) | 0.0356 (12) | 0.0217 (11) | 0.0057 (10) |
C13A | 0.0820 (16) | 0.0823 (18) | 0.0347 (11) | 0.0402 (14) | 0.0199 (11) | 0.0148 (11) |
C14A | 0.0860 (16) | 0.0796 (17) | 0.0441 (12) | 0.0460 (14) | 0.0245 (11) | 0.0318 (12) |
C15A | 0.0697 (14) | 0.0551 (13) | 0.0419 (11) | 0.0363 (11) | 0.0242 (10) | 0.0190 (9) |
C16A | 0.0366 (10) | 0.0417 (12) | 0.0479 (11) | 0.0188 (9) | 0.0101 (8) | 0.0073 (9) |
C17A | 0.0515 (12) | 0.0492 (13) | 0.0705 (14) | 0.0252 (10) | 0.0086 (11) | 0.0201 (11) |
C18A | 0.0654 (16) | 0.0665 (18) | 0.102 (2) | 0.0422 (14) | −0.0022 (15) | 0.0146 (15) |
C19A | 0.0583 (16) | 0.086 (2) | 0.108 (2) | 0.0489 (16) | 0.0061 (16) | −0.0042 (18) |
C20A | 0.0548 (14) | 0.100 (2) | 0.0815 (19) | 0.0355 (15) | 0.0307 (13) | 0.0060 (16) |
C21A | 0.0536 (12) | 0.0654 (16) | 0.0625 (13) | 0.0291 (11) | 0.0242 (11) | 0.0133 (11) |
C22A | 0.0441 (11) | 0.0612 (14) | 0.0438 (11) | 0.0241 (10) | 0.0020 (9) | 0.0082 (10) |
O1B | 0.1224 (14) | 0.0700 (12) | 0.0632 (10) | 0.0676 (11) | 0.0371 (10) | 0.0228 (9) |
O2B | 0.0970 (12) | 0.0692 (11) | 0.0602 (9) | 0.0393 (9) | 0.0497 (9) | 0.0255 (8) |
N1B | 0.0437 (8) | 0.0441 (9) | 0.0313 (8) | 0.0268 (7) | 0.0106 (6) | 0.0141 (7) |
N2B | 0.0487 (9) | 0.0467 (10) | 0.0325 (8) | 0.0280 (8) | 0.0119 (7) | 0.0152 (7) |
N3B | 0.0521 (10) | 0.0440 (10) | 0.0439 (9) | 0.0202 (8) | 0.0162 (8) | 0.0088 (8) |
C1B | 0.0371 (9) | 0.0379 (11) | 0.0354 (9) | 0.0179 (8) | 0.0104 (7) | 0.0132 (8) |
C2B | 0.0579 (12) | 0.0442 (12) | 0.0375 (10) | 0.0279 (10) | 0.0174 (9) | 0.0175 (9) |
C3B | 0.0544 (11) | 0.0423 (12) | 0.0440 (11) | 0.0270 (9) | 0.0141 (9) | 0.0169 (9) |
C4B | 0.0387 (9) | 0.0386 (11) | 0.0378 (10) | 0.0186 (8) | 0.0148 (8) | 0.0098 (8) |
C5B | 0.0496 (11) | 0.0473 (12) | 0.0363 (10) | 0.0227 (9) | 0.0168 (8) | 0.0172 (9) |
C6B | 0.0466 (10) | 0.0447 (12) | 0.0377 (10) | 0.0246 (9) | 0.0134 (8) | 0.0177 (8) |
C7B | 0.0420 (10) | 0.0422 (11) | 0.0317 (9) | 0.0225 (8) | 0.0122 (8) | 0.0152 (8) |
C8B | 0.0430 (10) | 0.0408 (11) | 0.0328 (9) | 0.0239 (8) | 0.0148 (8) | 0.0132 (8) |
C9B | 0.0441 (10) | 0.0421 (11) | 0.0350 (9) | 0.0244 (9) | 0.0131 (8) | 0.0162 (8) |
C10B | 0.0418 (10) | 0.0415 (11) | 0.0436 (10) | 0.0229 (9) | 0.0117 (8) | 0.0157 (9) |
C11B | 0.0759 (15) | 0.0872 (18) | 0.0492 (12) | 0.0599 (14) | 0.0179 (11) | 0.0200 (12) |
C12B | 0.0808 (17) | 0.092 (2) | 0.0747 (16) | 0.0646 (16) | 0.0245 (14) | 0.0173 (14) |
C13B | 0.0533 (13) | 0.0540 (14) | 0.0909 (17) | 0.0341 (11) | 0.0084 (12) | 0.0231 (13) |
C14B | 0.0498 (12) | 0.0577 (14) | 0.0749 (15) | 0.0274 (11) | 0.0093 (11) | 0.0345 (12) |
C15B | 0.0459 (11) | 0.0520 (13) | 0.0542 (12) | 0.0249 (10) | 0.0125 (9) | 0.0258 (10) |
C16B | 0.0433 (10) | 0.0432 (11) | 0.0327 (9) | 0.0268 (9) | 0.0118 (8) | 0.0133 (8) |
C17B | 0.0602 (12) | 0.0483 (13) | 0.0409 (10) | 0.0222 (10) | 0.0160 (9) | 0.0185 (9) |
C18B | 0.0757 (15) | 0.0690 (16) | 0.0437 (11) | 0.0392 (13) | 0.0259 (11) | 0.0289 (11) |
C19B | 0.0653 (13) | 0.0725 (16) | 0.0360 (10) | 0.0463 (13) | 0.0161 (10) | 0.0129 (11) |
C20B | 0.0564 (12) | 0.0475 (13) | 0.0465 (11) | 0.0250 (10) | 0.0097 (10) | 0.0016 (10) |
C21B | 0.0558 (12) | 0.0445 (12) | 0.0462 (11) | 0.0215 (10) | 0.0189 (9) | 0.0139 (9) |
C22B | 0.0592 (12) | 0.0727 (15) | 0.0358 (10) | 0.0450 (11) | 0.0085 (9) | 0.0181 (10) |
O1A—N3A | 1.2234 (19) | O1B—N3B | 1.229 (2) |
O2A—N3A | 1.223 (2) | O2B—N3B | 1.215 (2) |
N1A—C7A | 1.372 (2) | N1B—C7B | 1.370 (2) |
N1A—C8A | 1.389 (2) | N1B—C8B | 1.379 (2) |
N1A—C22A | 1.465 (2) | N1B—C22B | 1.469 (2) |
N2A—C7A | 1.328 (2) | N2B—C7B | 1.325 (2) |
N2A—C9A | 1.375 (2) | N2B—C9B | 1.378 (2) |
N3A—C4A | 1.465 (2) | N3B—C4B | 1.470 (2) |
C1A—C6A | 1.397 (2) | C1B—C6B | 1.398 (2) |
C1A—C2A | 1.402 (2) | C1B—C2B | 1.399 (2) |
C1A—C7A | 1.467 (2) | C1B—C7B | 1.468 (2) |
C2A—C3A | 1.377 (3) | C2B—C3B | 1.384 (3) |
C2A—H2A | 0.9600 | C2B—H2B | 0.9600 |
C3A—C4A | 1.385 (2) | C3B—C4B | 1.375 (2) |
C3A—H3A | 0.9600 | C3B—H3B | 0.9600 |
C4A—C5A | 1.380 (2) | C4B—C5B | 1.378 (3) |
C5A—C6A | 1.379 (3) | C5B—C6B | 1.374 (3) |
C5A—H5A | 0.9599 | C5B—H5B | 0.9600 |
C6A—H6A | 0.9599 | C6B—H6B | 0.9600 |
C8A—C9A | 1.374 (2) | C8B—C9B | 1.376 (2) |
C8A—C16A | 1.478 (3) | C8B—C16B | 1.492 (2) |
C9A—C10A | 1.478 (2) | C9B—C10B | 1.472 (2) |
C10A—C11A | 1.388 (3) | C10B—C15B | 1.387 (2) |
C10A—C15A | 1.393 (3) | C10B—C11B | 1.391 (3) |
C11A—C12A | 1.387 (3) | C11B—C12B | 1.392 (3) |
C11A—H11A | 0.9601 | C11B—H11B | 0.9601 |
C12A—C13A | 1.376 (3) | C12B—C13B | 1.372 (3) |
C12A—H12A | 0.9600 | C12B—H12B | 0.9599 |
C13A—C14A | 1.373 (3) | C13B—C14B | 1.372 (3) |
C13A—H13A | 0.9600 | C13B—H13B | 0.9600 |
C14A—C15A | 1.387 (3) | C14B—C15B | 1.381 (3) |
C14A—H14A | 0.9599 | C14B—H14B | 0.9601 |
C15A—H15A | 0.9601 | C15B—H15B | 0.9601 |
C16A—C17A | 1.389 (3) | C16B—C21B | 1.379 (3) |
C16A—C21A | 1.392 (3) | C16B—C17B | 1.384 (3) |
C17A—C18A | 1.381 (3) | C17B—C18B | 1.382 (3) |
C17A—H17A | 0.9600 | C17B—H17B | 0.9601 |
C18A—C19A | 1.367 (4) | C18B—C19B | 1.371 (3) |
C18A—H18A | 0.9600 | C18B—H18B | 0.9598 |
C19A—C20A | 1.380 (4) | C19B—C20B | 1.365 (3) |
C19A—H19A | 0.9601 | C19B—H19B | 0.9600 |
C20A—C21A | 1.391 (3) | C20B—C21B | 1.387 (3) |
C20A—H20A | 0.9599 | C20B—H20B | 0.9602 |
C21A—H21A | 0.9598 | C21B—H21B | 0.9600 |
C22A—H22A | 0.9600 | C22B—H22D | 0.9600 |
C22A—H22B | 0.9600 | C22B—H22E | 0.9600 |
C22A—H22C | 0.9600 | C22B—H22F | 0.9600 |
C7A—N1A—C8A | 106.88 (14) | C7B—N1B—C8B | 106.94 (13) |
C7A—N1A—C22A | 127.75 (15) | C7B—N1B—C22B | 127.83 (15) |
C8A—N1A—C22A | 124.73 (15) | C8B—N1B—C22B | 124.76 (14) |
C7A—N2A—C9A | 106.11 (14) | C7B—N2B—C9B | 106.31 (13) |
O2A—N3A—O1A | 122.90 (16) | O2B—N3B—O1B | 123.56 (18) |
O2A—N3A—C4A | 118.73 (15) | O2B—N3B—C4B | 118.61 (18) |
O1A—N3A—C4A | 118.36 (16) | O1B—N3B—C4B | 117.81 (17) |
C6A—C1A—C2A | 117.99 (16) | C6B—C1B—C2B | 118.21 (17) |
C6A—C1A—C7A | 124.10 (17) | C6B—C1B—C7B | 118.27 (16) |
C2A—C1A—C7A | 117.83 (15) | C2B—C1B—C7B | 123.51 (15) |
C3A—C2A—C1A | 121.57 (16) | C3B—C2B—C1B | 120.74 (17) |
C3A—C2A—H2A | 118.7 | C3B—C2B—H2B | 119.6 |
C1A—C2A—H2A | 119.7 | C1B—C2B—H2B | 119.6 |
C2A—C3A—C4A | 118.37 (17) | C4B—C3B—C2B | 118.74 (18) |
C2A—C3A—H3A | 122.2 | C4B—C3B—H3B | 121.6 |
C4A—C3A—H3A | 119.4 | C2B—C3B—H3B | 119.7 |
C5A—C4A—C3A | 121.98 (16) | C3B—C4B—C5B | 122.35 (17) |
C5A—C4A—N3A | 118.70 (15) | C3B—C4B—N3B | 118.71 (17) |
C3A—C4A—N3A | 119.33 (16) | C5B—C4B—N3B | 118.93 (16) |
C6A—C5A—C4A | 118.85 (16) | C6B—C5B—C4B | 118.41 (16) |
C6A—C5A—H5A | 121.1 | C6B—C5B—H5B | 120.3 |
C4A—C5A—H5A | 120.1 | C4B—C5B—H5B | 121.3 |
C5A—C6A—C1A | 121.24 (17) | C5B—C6B—C1B | 121.54 (18) |
C5A—C6A—H6A | 119.6 | C5B—C6B—H6B | 119.0 |
C1A—C6A—H6A | 119.1 | C1B—C6B—H6B | 119.4 |
N2A—C7A—N1A | 111.05 (15) | N2B—C7B—N1B | 111.03 (15) |
N2A—C7A—C1A | 122.00 (16) | N2B—C7B—C1B | 123.14 (14) |
N1A—C7A—C1A | 126.94 (15) | N1B—C7B—C1B | 125.82 (15) |
C9A—C8A—N1A | 105.76 (15) | C9B—C8B—N1B | 106.27 (14) |
C9A—C8A—C16A | 131.11 (16) | C9B—C8B—C16B | 133.56 (16) |
N1A—C8A—C16A | 123.07 (16) | N1B—C8B—C16B | 120.17 (14) |
C8A—C9A—N2A | 110.19 (15) | C8B—C9B—N2B | 109.45 (15) |
C8A—C9A—C10A | 130.01 (17) | C8B—C9B—C10B | 130.01 (16) |
N2A—C9A—C10A | 119.79 (15) | N2B—C9B—C10B | 120.54 (15) |
C11A—C10A—C15A | 117.99 (16) | C15B—C10B—C11B | 117.15 (18) |
C11A—C10A—C9A | 122.71 (17) | C15B—C10B—C9B | 119.84 (17) |
C15A—C10A—C9A | 119.27 (17) | C11B—C10B—C9B | 123.00 (17) |
C12A—C11A—C10A | 120.96 (19) | C10B—C11B—C12B | 121.1 (2) |
C12A—C11A—H11A | 119.7 | C10B—C11B—H11B | 119.1 |
C10A—C11A—H11A | 119.4 | C12B—C11B—H11B | 119.8 |
C13A—C12A—C11A | 120.2 (2) | C13B—C12B—C11B | 120.3 (2) |
C13A—C12A—H12A | 120.1 | C13B—C12B—H12B | 120.2 |
C11A—C12A—H12A | 119.7 | C11B—C12B—H12B | 119.5 |
C14A—C13A—C12A | 119.73 (19) | C12B—C13B—C14B | 119.5 (2) |
C14A—C13A—H13A | 120.0 | C12B—C13B—H13B | 120.7 |
C12A—C13A—H13A | 120.2 | C14B—C13B—H13B | 119.9 |
C13A—C14A—C15A | 120.3 (2) | C13B—C14B—C15B | 120.2 (2) |
C13A—C14A—H14A | 120.4 | C13B—C14B—H14B | 120.1 |
C15A—C14A—H14A | 119.3 | C15B—C14B—H14B | 119.7 |
C14A—C15A—C10A | 120.8 (2) | C14B—C15B—C10B | 121.8 (2) |
C14A—C15A—H15A | 119.7 | C14B—C15B—H15B | 119.0 |
C10A—C15A—H15A | 119.5 | C10B—C15B—H15B | 119.2 |
C17A—C16A—C21A | 118.40 (19) | C21B—C16B—C17B | 119.14 (17) |
C17A—C16A—C8A | 122.23 (19) | C21B—C16B—C8B | 120.90 (17) |
C21A—C16A—C8A | 119.33 (19) | C17B—C16B—C8B | 119.92 (17) |
C18A—C17A—C16A | 121.3 (3) | C18B—C17B—C16B | 120.05 (19) |
C18A—C17A—H17A | 119.7 | C18B—C17B—H17B | 120.3 |
C16A—C17A—H17A | 119.0 | C16B—C17B—H17B | 119.7 |
C19A—C18A—C17A | 119.8 (3) | C19B—C18B—C17B | 120.3 (2) |
C19A—C18A—H18A | 120.7 | C19B—C18B—H18B | 119.9 |
C17A—C18A—H18A | 119.4 | C17B—C18B—H18B | 119.8 |
C18A—C19A—C20A | 120.2 (3) | C20B—C19B—C18B | 120.14 (19) |
C18A—C19A—H19A | 117.4 | C20B—C19B—H19B | 119.9 |
C20A—C19A—H19A | 122.4 | C18B—C19B—H19B | 119.9 |
C19A—C20A—C21A | 120.3 (3) | C19B—C20B—C21B | 120.0 (2) |
C19A—C20A—H20A | 119.0 | C19B—C20B—H20B | 119.8 |
C21A—C20A—H20A | 120.7 | C21B—C20B—H20B | 120.2 |
C20A—C21A—C16A | 120.0 (3) | C16B—C21B—C20B | 120.36 (19) |
C20A—C21A—H21A | 121.1 | C16B—C21B—H21B | 119.5 |
C16A—C21A—H21A | 118.9 | C20B—C21B—H21B | 120.2 |
N1A—C22A—H22A | 109.5 | N1B—C22B—H22D | 109.5 |
N1A—C22A—H22B | 109.5 | N1B—C22B—H22E | 109.5 |
H22A—C22A—H22B | 109.5 | H22D—C22B—H22E | 109.5 |
N1A—C22A—H22C | 109.5 | N1B—C22B—H22F | 109.5 |
H22A—C22A—H22C | 109.5 | H22D—C22B—H22F | 109.5 |
H22B—C22A—H22C | 109.5 | H22E—C22B—H22F | 109.5 |
C6A—C1A—C2A—C3A | −0.1 (3) | C6B—C1B—C2B—C3B | −1.2 (3) |
C7A—C1A—C2A—C3A | 176.97 (17) | C7B—C1B—C2B—C3B | −179.60 (17) |
C1A—C2A—C3A—C4A | −0.1 (3) | C1B—C2B—C3B—C4B | 0.9 (3) |
C2A—C3A—C4A—C5A | 0.1 (3) | C2B—C3B—C4B—C5B | −0.2 (3) |
C2A—C3A—C4A—N3A | −179.65 (16) | C2B—C3B—C4B—N3B | −178.56 (17) |
O2A—N3A—C4A—C5A | 166.38 (17) | O2B—N3B—C4B—C3B | 168.45 (18) |
O1A—N3A—C4A—C5A | −13.5 (2) | O1B—N3B—C4B—C3B | −12.4 (3) |
O2A—N3A—C4A—C3A | −13.9 (2) | O2B—N3B—C4B—C5B | −10.0 (3) |
O1A—N3A—C4A—C3A | 166.25 (17) | O1B—N3B—C4B—C5B | 169.13 (18) |
C3A—C4A—C5A—C6A | 0.1 (3) | C3B—C4B—C5B—C6B | −0.2 (3) |
N3A—C4A—C5A—C6A | 179.87 (17) | N3B—C4B—C5B—C6B | 178.17 (16) |
C4A—C5A—C6A—C1A | −0.3 (3) | C4B—C5B—C6B—C1B | −0.1 (3) |
C2A—C1A—C6A—C5A | 0.3 (3) | C2B—C1B—C6B—C5B | 0.8 (3) |
C7A—C1A—C6A—C5A | −176.55 (18) | C7B—C1B—C6B—C5B | 179.29 (16) |
C9A—N2A—C7A—N1A | −0.5 (2) | C9B—N2B—C7B—N1B | 0.1 (2) |
C9A—N2A—C7A—C1A | 179.23 (16) | C9B—N2B—C7B—C1B | −178.86 (16) |
C8A—N1A—C7A—N2A | 0.9 (2) | C8B—N1B—C7B—N2B | 0.0 (2) |
C22A—N1A—C7A—N2A | 172.01 (17) | C22B—N1B—C7B—N2B | 172.35 (18) |
C8A—N1A—C7A—C1A | −178.80 (17) | C8B—N1B—C7B—C1B | 178.92 (17) |
C22A—N1A—C7A—C1A | −7.7 (3) | C22B—N1B—C7B—C1B | −8.7 (3) |
C6A—C1A—C7A—N2A | 152.45 (18) | C6B—C1B—C7B—N2B | −30.7 (3) |
C2A—C1A—C7A—N2A | −24.4 (3) | C2B—C1B—C7B—N2B | 147.70 (19) |
C6A—C1A—C7A—N1A | −27.8 (3) | C6B—C1B—C7B—N1B | 150.49 (18) |
C2A—C1A—C7A—N1A | 155.31 (18) | C2B—C1B—C7B—N1B | −31.1 (3) |
C7A—N1A—C8A—C9A | −0.9 (2) | C7B—N1B—C8B—C9B | −0.09 (19) |
C22A—N1A—C8A—C9A | −172.36 (17) | C22B—N1B—C8B—C9B | −172.74 (17) |
C7A—N1A—C8A—C16A | 176.44 (17) | C7B—N1B—C8B—C16B | 179.86 (16) |
C22A—N1A—C8A—C16A | 5.0 (3) | C22B—N1B—C8B—C16B | 7.2 (3) |
N1A—C8A—C9A—N2A | 0.7 (2) | N1B—C8B—C9B—N2B | 0.2 (2) |
C16A—C8A—C9A—N2A | −176.43 (19) | C16B—C8B—C9B—N2B | −179.79 (19) |
N1A—C8A—C9A—C10A | −177.95 (18) | N1B—C8B—C9B—C10B | 179.49 (18) |
C16A—C8A—C9A—C10A | 5.0 (4) | C16B—C8B—C9B—C10B | −0.4 (4) |
C7A—N2A—C9A—C8A | −0.1 (2) | C7B—N2B—C9B—C8B | −0.2 (2) |
C7A—N2A—C9A—C10A | 178.66 (16) | C7B—N2B—C9B—C10B | −179.57 (16) |
C8A—C9A—C10A—C11A | 26.5 (3) | C8B—C9B—C10B—C15B | −166.60 (19) |
N2A—C9A—C10A—C11A | −151.96 (19) | N2B—C9B—C10B—C15B | 12.7 (3) |
C8A—C9A—C10A—C15A | −155.6 (2) | C8B—C9B—C10B—C11B | 12.6 (3) |
N2A—C9A—C10A—C15A | 25.9 (3) | N2B—C9B—C10B—C11B | −168.1 (2) |
C15A—C10A—C11A—C12A | 1.5 (3) | C15B—C10B—C11B—C12B | 0.5 (3) |
C9A—C10A—C11A—C12A | 179.43 (19) | C9B—C10B—C11B—C12B | −178.8 (2) |
C10A—C11A—C12A—C13A | −1.6 (3) | C10B—C11B—C12B—C13B | −0.1 (4) |
C11A—C12A—C13A—C14A | 0.6 (4) | C11B—C12B—C13B—C14B | −0.5 (4) |
C12A—C13A—C14A—C15A | 0.5 (4) | C12B—C13B—C14B—C15B | 0.6 (4) |
C13A—C14A—C15A—C10A | −0.6 (3) | C13B—C14B—C15B—C10B | −0.2 (3) |
C11A—C10A—C15A—C14A | −0.4 (3) | C11B—C10B—C15B—C14B | −0.3 (3) |
C9A—C10A—C15A—C14A | −178.37 (19) | C9B—C10B—C15B—C14B | 178.95 (18) |
C9A—C8A—C16A—C17A | −126.2 (2) | C9B—C8B—C16B—C21B | 82.2 (3) |
N1A—C8A—C16A—C17A | 57.2 (3) | N1B—C8B—C16B—C21B | −97.8 (2) |
C9A—C8A—C16A—C21A | 51.4 (3) | C9B—C8B—C16B—C17B | −100.1 (3) |
N1A—C8A—C16A—C21A | −125.2 (2) | N1B—C8B—C16B—C17B | 79.9 (2) |
C21A—C16A—C17A—C18A | −1.0 (3) | C21B—C16B—C17B—C18B | −0.2 (3) |
C8A—C16A—C17A—C18A | 176.61 (19) | C8B—C16B—C17B—C18B | −177.97 (17) |
C16A—C17A—C18A—C19A | 0.0 (4) | C16B—C17B—C18B—C19B | 0.7 (3) |
C17A—C18A—C19A—C20A | 1.0 (4) | C17B—C18B—C19B—C20B | −0.9 (3) |
C18A—C19A—C20A—C21A | −1.0 (4) | C18B—C19B—C20B—C21B | 0.6 (3) |
C19A—C20A—C21A—C16A | −0.1 (4) | C17B—C16B—C21B—C20B | 0.0 (3) |
C17A—C16A—C21A—C20A | 1.1 (3) | C8B—C16B—C21B—C20B | 177.69 (16) |
C8A—C16A—C21A—C20A | −176.65 (19) | C19B—C20B—C21B—C16B | −0.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12a—H12a···O1ai | 0.96 | 2.66 | 3.544 (3) | 154 |
C14a—H14a···O2bii | 0.96 | 2.63 | 3.258 (3) | 124 |
C18b—H18b···O1ai | 0.96 | 2.69 | 3.245 (3) | 118 |
C19b—H19b···O1bi | 0.96 | 2.58 | 3.431 (3) | 148 |
Symmetry codes: (i) x, y−1, z−1; (ii) x, y, z−1. |
Experimental details
(I) | (II) | (III) | (IV) | |
Crystal data | ||||
Chemical formula | C21H15N3O2 | C21H15N3O2·C2H3N | C21H15N3O2·CH4O | C22H17N3O2·CH4O |
Mr | 341.36 | 382.41 | 373.40 | 387.43 |
Crystal system, space group | Monoclinic, Cc | Orthorhombic, Pbca | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 293 | 293 | 293 | 293 |
a, b, c (Å) | 10.521 (2), 19.769 (4), 9.056 (2) | 9.111 (2), 18.830 (4), 23.754 (5) | 11.728 (2), 11.365 (2), 29.241 (6) | 5.813 (1), 15.003 (3), 23.243 (5) |
α, β, γ (°) | 90, 111.49 (3), 90 | 90, 90, 90 | 90, 94.62 (2), 90 | 90, 95.480 (3), 90 |
V (Å3) | 1752.6 (7) | 4075.2 (15) | 3884.8 (12) | 2017.8 (7) |
Z | 4 | 8 | 8 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.08 | 0.09 | 0.09 |
Crystal size (mm) | 0.59 × 0.37 × 0.08 | 0.50 × 0.09 × 0.05 | 0.20 × 0.20 × 0.05 | 0.09 × 0.02 × 0.02 |
Data collection | ||||
Diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer | Nonius Kappa CCD diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6192, 1533, 943 | 6703, 3584, 1506 | 22154, 6747, 2718 | 11012, 3292, 1604 |
Rint | 0.083 | 0.080 | 0.105 | 0.084 |
(sin θ/λ)max (Å−1) | 0.596 | 0.595 | 0.595 | 0.595 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.090, 0.88 | 0.047, 0.106, 0.81 | 0.067, 0.156, 0.88 | 0.059, 0.150, 0.91 |
No. of reflections | 1533 | 3584 | 6747 | 3292 |
No. of parameters | 236 | 263 | 505 | 263 |
No. of restraints | 2 | 0 | 0 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.12, −0.13 | 0.15, −0.16 | 0.17, −0.18 | 0.15, −0.24 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | ? | ? | ? |
Absolute structure parameter | 0 (10) | ? | ? | ? |
(V) | (VI) | |
Crystal data | ||
Chemical formula | C22H17N3O2 | C22H17N3O2 |
Mr | 355.39 | 355.39 |
Crystal system, space group | Monoclinic, P21/c | Triclinic, P1 |
Temperature (K) | 293 | 293 |
a, b, c (Å) | 16.242 (3), 9.583 (2), 11.615 (2) | 11.855 (2), 12.384 (2), 14.791 (3) |
α, β, γ (°) | 90, 94.36 (2), 90 | 111.95 (3), 99.56 (3), 109.63 (3) |
V (Å3) | 1802.6 (6) | 1788.2 (10) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.09 |
Crystal size (mm) | 0.08 × 0.03 × 0.01 | 0.50 × 0.05 × 0.05 |
Data collection | ||
Diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10123, 3139, 1975 | 14497, 6250, 4081 |
Rint | 0.055 | 0.091 |
(sin θ/λ)max (Å−1) | 0.597 | 0.595 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.154, 1.09 | 0.044, 0.130, 0.89 |
No. of reflections | 3139 | 6248 |
No. of parameters | 244 | 489 |
No. of restraints | 0 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.21 | 0.16, −0.19 |
Absolute structure | ? | ? |
Absolute structure parameter | ? | ? |
Computer programs: COLLECT (Nonius, 2000), DENZO HKL-2000 (Otwinowski & Minor ,1997), DENZO HKL-2000 (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1999).
Ph rotation at position 2 | Ph rotation at position 4 | Ph rotation at position 5 | |
(I) | 44.8 (2) | 45.0 (2) | 34.3 (2) |
(II) | 45.5 (1) | 41.0 (2) | 33.1 (1) |
(IIIa) | 15.7 (2) | 37.4 (2) | 46.5 (2) |
(IIIb) | 31.5 (1) | 30.9 (2) | 35.3 (2) |
(IV) | 85.2 (1) | 69.5 (1) | 24.3 (2) |
(V) | 30.5 (1) | 65.5 (1) | 24.2 (1) |
(VIa) | 26.0 (1) | 54.5 (1) | 25.8 (2) |
(VIb) | 30.8 (1) | 81.1 (1) | 12.5 (2) |
Compound | D—H···A | D—H | H···A | D···A | D—H···A |
(I) | |||||
N1—H1···N2i | 0.86 | 2.10 | 2.942 (5) | 165 | |
(II) | |||||
N1—H1···N2ii | 0.99 | 1.97 | 2.920 (3) | 161 | |
(III) | |||||
N1a—H1a···O3a | 0.86 | 1.96 | 2.819 (4) | 175 | |
N1b—H1b···O3biii | 0.86 | 1.95 | 2.788 (4) | 166 | |
O3a—H3Oa···N2biii | 0.82 | 1.98 | 2.791 (4) | 171 | |
O3b—H3Ob···N2a | 0.82 | 1.98 | 2.792 (4) | 169 | |
(IV) | |||||
C18—H18···O2iv | 0.96 | 2.56 | 3.426 (4) | 150 | |
(V) | |||||
C4—H4···O1v | 0.96 | 2.48 | 3.148 (3) | 127 | |
(VI) | |||||
C12a—H12a···O1avi | 0.96 | 2.66 | 3.544 (3) | 154 | |
C14b—H14b···O2bvii | 0.96 | 2.63 | 3.258 (3) | 124 | |
C18b—H18b···O1avi | 0.96 | 2.69 | 3.241 (3) | 118 | |
C19b—H19b···O1bvi | 0.96 | 2.58 | 3.431 (3) | 148 |
Symmetry codes: (i) x, -y, 1/2+z; (ii) 1/2-x, y, 3/2-z; (iii) 1-x, -1/2+y, 1/2-z; (iv) 1-x, 1-y, 1-z; (v) x, 5/2-y, 1/2+z; (vi) x, -1+y, -1+z; (vi) x, y, -1+z. |
Recently, heterocyclic imidazole derivatives have attracted considerable attention because of their unique linear and nonlinear optical properties (Santos et al., 2001). Lophine (2,4,5-triphenyl-1H-imidazole) is an attractive fluorescence and chemiluminescence compound. The chemiluminescence properties of lophine were reported for the first time by Radziszewski (1877) who showed that it emits yellow light when it reacts with oxygen in the presence of a strong base. The chemistry of lophine derivatives has a long history in relation to important physicochemical phenomena such as chemiluminescence through its oxidation and photo-, piezo- and thermochromic properties (Zimmerman et al., 1961; Maeda & Hayashi, 1969, 1970). Only a few imidazole analogues or nitro lophine derivatives are known (Inouye & Sakaino, 1985,1986, 2000; Sakaino, Fujii et al., 1990; Sakaino, Shimizu et al., 1990; Kaftory et al., 1998; Inouye et al., 2003; Bu et al., 2003). The spectral properties of lophine derivatives are of interest: the colour change is dependent on the solvation in the crystal and in different derivatives. We have recently synthesized various lophine derivatives to study their spectral properties with the aim of understanding the relationship between molecular and crystal structures and colour change (Fridman, Kaftory, Eichen et al., 2007; Fridman, Kaftory & Speiser, 2007; Fridman et al., 2008). In order to examine the effect of the imidazole ring's ability to form hydrogen bonds on the crystal colour, we have prepared lophine derivatives with nitrophenyl at position 2 of the imidazole (for notation see scheme) as well as compounds where the hydrogen donor ability is blocked (N—H) in imidazole by replacing the H atom by a methyl group. We present here a comparison between molecular and crystal structures of six lophine o-, m- and p-nitrophenyl derivatives (Fig. 1–6).
Comparison of the bond lengths in the imidazole rings of (I) to (IV) reveals the following ranges: N1—C7 1.350–1.375 Å, N2—C7 1.317–1.333 Å, N1—C8 1.377–1.395 Å, N2—C9 1.369–1.383 Å and C8—C9 1.374–1.377 Å. Statistical calculation of the related bond lengths in the imidazole rings in 56 lophine derivatives taken from the Cambridge Structural Database (CSD; Allen, 2002) provided corresponding average values of 1.353 (8), 1.333 (7), 1.370 (16), 1.386 (7) and 1.375 (8) Å, respectively.
The conformation of the molecules differs by rotation of the phenyl rings with respect to the central imidazole. The conformation is affected by the presence or absence of a bulky group [H atom in (I)–(III) and methyl group in (IV)–(VI)], and is also dependent on the position of the nitro group (o, m, p) on the phenyl ring at position 2 of the imidazole with respect to the H atom or methyl group. An overlay of the molecules in the six crystals [only one of the two molecules of (III) and (VI) is shown] is shown in Figs. 7(a) and 7(b), and the rotation angles of the phenyl rings are given in Table 1. The main difference between the conformation of molecule (I) and (III) is the rotation of the phenyl ring at position 2. The rotation angles in (I) and (II) are 44.8 (7) and 45.5 (4)°, respectively, compared with 15.7 (5)° and 31.5 (6)° in molecules (IIIa) and (IIIb), respectively. This difference can be explained by the larger repulsion of the nitro group in the ortho position compared with that in the para position. In the presence of a methyl group, the rotation angle decreases in the sequence: nitro at the ortho position (IV) > meta position (V) > para position (VI) [85.2 (1)°, 36.0 (1)°, 26.0 (1)° (VIa) and 30.8 (1)° (VIb), respectively]. It should be noted that the conformation of the two crystallographically independent molecules in (VI) are different with respect to the rotation of the phenyl rings in positions 4 and 5 (see notation in the scheme). The effect of the methyl group is also seen in the bond angles C1—C7—N1 and C1—C7—N2, where the bond angle is larger on the side with the methyl group: 124.7 (3) and 123.2 (3)° in (IV), 126.1 (2) and 122.6 (2)° in (V), 126.9 (2) and 122.2 (2)° in (VIa), and 125.8 (2) and 123.2 (2)° in (VIb), respectively. In the absence of the methyl group [compounds (I)–(III)] the opposite relation between values of the equivalent bond angles is observed: 123.2 (3) and 126.1 (3)° in (I), 122.9 (2) and 125.2 (2)° (nitro group in ortho position) in (II), 124.4 (3) and 125.2 (3)° in(IIIa), and 124.1 (3)° and 125.3 (3)° (nitro group in para position) in (IIIb).
The molecular packing is similar in compounds (I)–(III) as they all form folded chains comprising molecules bonded to each other by hydrogen bonds. However, while in the crystals of (I) and (II) the molecules are connected to each other through N—H···N hydrogen bonds, in (III) a mediator molecule, methanol, forms the hydrogen bonds between each pair of molecules of (III). The hydrogen-bonding schemes are shown in Figs. 8–10, and the geometry of the hydrogen bonds is given in Table 2. A similar chain formation by hydrogen bonds has been observed in five other lophine derivatives (Seethalakshmi et al., 2006; Inouye & Sakaino, 1986; Thuer et al., 2004; Liu et al., 2005, Thiruvalluvar et al., 2007). While the methanol solvent molecule in (III) has a specific role in the packing arrangement as described above, the role of the acetonitrile molecules in solvate (II) is to occupy lattice voids. In the absence of the hydrogen donor (N—H) of the imidazole, the packing of molecules in (IV)–(VI) is determined by much weaker intermolecular interactions such as weak hydrogen bonds between the O atoms of the nitro group and aromatic H atoms (Table 2). The methanol solvent in (IV), although hydrogen bonded to the imidazole, does not play any significant role in the molecular packing [the HO···N distance is 2.823 (4) Å]. Differential scanning calorimetry (DSC) thermographs (see Supplementary material) show that the solvent molecules are removed at 394 and 377 K for (II) and (III), respectively. Upon removal of acetonitrile from (II) there is no change in the crystal colour, whereas removal of the methanol from (III) changes the crystal colour to red. It is therefore suggested that the change of colour is a result of the change in the hydrogen bonding. This assumption needs further investigation.