Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0021889807007704/kk5009sup1.cif | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0021889807007704/kk5009sup2.pdf | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889807007704/kk50093asup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889807007704/kk50093bsup4.hkl |
CCDC references: 650783; 650784
For both compounds, data collection: Bruker SMART; cell refinement: Bruker SMART; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.
C20H14N2O | Dx = 1.294 Mg m−3 |
Mr = 298.33 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, I41/a | Cell parameters from 2975 reflections |
Hall symbol: -I4ad | θ = 2.7–20.7° |
a = 21.5111 (7) Å | µ = 0.08 mm−1 |
c = 13.2377 (9) Å | T = 298 K |
V = 6125.4 (5) Å3 | Prism, yellow |
Z = 16 | 0.16 × 0.13 × 0.10 mm |
F(000) = 2496 |
CCD area detector diffractometer | 1932 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.057 |
Graphite monochromator | θmax = 27.6°, θmin = 1.8° |
phi and ω scans | h = −28→24 |
25513 measured reflections | k = −25→28 |
3576 independent reflections | l = −17→15 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0769P)2 + 2.3111P] where P = (Fo2 + 2Fc2)/3 |
3576 reflections | (Δ/σ)max < 0.001 |
209 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C20H14N2O | Z = 16 |
Mr = 298.33 | Mo Kα radiation |
Tetragonal, I41/a | µ = 0.08 mm−1 |
a = 21.5111 (7) Å | T = 298 K |
c = 13.2377 (9) Å | 0.16 × 0.13 × 0.10 mm |
V = 6125.4 (5) Å3 |
CCD area detector diffractometer | 1932 reflections with I > 2σ(I) |
25513 measured reflections | Rint = 0.057 |
3576 independent reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.48 e Å−3 |
3576 reflections | Δρmin = −0.19 e Å−3 |
209 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 | ||
O1 | 0.98766 (8) | 0.43660 (8) | 0.22082 (12) | 0.0798 (5) | |
H1 | 0.9615 | 0.4642 | 0.2251 | 0.120* | |
N1 | 0.90921 (8) | 0.48603 (8) | 0.08379 (12) | 0.0559 (5) | |
N2 | 0.74190 (8) | 0.65311 (8) | 0.12063 (12) | 0.0559 (4) | |
C1 | 0.94769 (9) | 0.43967 (9) | 0.05313 (15) | 0.0520 (5) | |
C2 | 0.98875 (10) | 0.41431 (10) | 0.12548 (16) | 0.0574 (6) | |
C3 | 1.02810 (11) | 0.36736 (11) | 0.10049 (18) | 0.0690 (6) | |
H3 | 1.0553 | 0.3514 | 0.1485 | 0.083* | |
C4 | 1.02754 (12) | 0.34306 (12) | 0.00223 (19) | 0.0753 (7) | |
H4 | 1.0544 | 0.3107 | −0.0141 | 0.090* | |
C5 | 0.98868 (11) | 0.36573 (11) | −0.06935 (18) | 0.0691 (6) | |
H5 | 0.9889 | 0.3487 | −0.1339 | 0.083* | |
C6 | 0.94782 (10) | 0.41518 (10) | −0.04633 (15) | 0.0575 (5) | |
C7 | 0.90691 (11) | 0.44311 (12) | −0.11538 (16) | 0.0714 (7) | |
H7 | 0.9055 | 0.4293 | −0.1819 | 0.086* | |
C8 | 0.86941 (12) | 0.49024 (12) | −0.08526 (17) | 0.0736 (7) | |
H8 | 0.8427 | 0.5089 | −0.1313 | 0.088* | |
C9 | 0.87084 (10) | 0.51109 (10) | 0.01616 (15) | 0.0582 (5) | |
C10 | 0.82756 (11) | 0.55910 (11) | 0.05060 (17) | 0.0665 (6) | |
H10 | 0.8035 | 0.5795 | 0.0025 | 0.080* | |
C11 | 0.82074 (11) | 0.57513 (11) | 0.14698 (17) | 0.0656 (6) | |
H11 | 0.8477 | 0.5573 | 0.1936 | 0.079* | |
C12 | 0.77402 (10) | 0.61880 (10) | 0.18570 (16) | 0.0579 (5) | |
C13 | 0.76375 (11) | 0.62140 (11) | 0.29078 (17) | 0.0683 (6) | |
H13 | 0.7873 | 0.5967 | 0.3339 | 0.082* | |
C14 | 0.71975 (11) | 0.65964 (11) | 0.32903 (16) | 0.0686 (6) | |
H14 | 0.7129 | 0.6614 | 0.3983 | 0.082* | |
C15 | 0.68429 (10) | 0.69691 (10) | 0.26286 (15) | 0.0551 (5) | |
C16 | 0.63792 (11) | 0.73834 (11) | 0.29527 (18) | 0.0691 (6) | |
H16 | 0.6288 | 0.7416 | 0.3637 | 0.083* | |
C17 | 0.60639 (11) | 0.77350 (12) | 0.22773 (18) | 0.0723 (7) | |
H17 | 0.5757 | 0.8007 | 0.2502 | 0.087* | |
C18 | 0.61954 (11) | 0.76925 (11) | 0.12414 (17) | 0.0681 (6) | |
H18 | 0.5979 | 0.7939 | 0.0785 | 0.082* | |
C19 | 0.66387 (10) | 0.72916 (10) | 0.09005 (16) | 0.0591 (6) | |
H19 | 0.6719 | 0.7263 | 0.0212 | 0.071* | |
C20 | 0.69748 (9) | 0.69212 (9) | 0.15827 (14) | 0.0504 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0864 (13) | 0.0916 (13) | 0.0612 (10) | 0.0231 (9) | −0.0134 (8) | −0.0112 (8) |
N1 | 0.0569 (11) | 0.0568 (11) | 0.0540 (9) | 0.0025 (9) | 0.0015 (8) | −0.0010 (8) |
N2 | 0.0576 (11) | 0.0594 (11) | 0.0507 (9) | 0.0033 (9) | −0.0015 (8) | −0.0041 (8) |
C1 | 0.0512 (12) | 0.0507 (12) | 0.0542 (11) | −0.0004 (10) | 0.0062 (9) | 0.0021 (9) |
C2 | 0.0581 (13) | 0.0620 (13) | 0.0521 (12) | 0.0000 (11) | 0.0018 (10) | −0.0034 (10) |
C3 | 0.0645 (14) | 0.0732 (16) | 0.0693 (15) | 0.0148 (12) | −0.0005 (11) | −0.0011 (12) |
C4 | 0.0780 (17) | 0.0712 (16) | 0.0766 (16) | 0.0172 (13) | 0.0150 (13) | −0.0038 (13) |
C5 | 0.0752 (16) | 0.0729 (16) | 0.0593 (13) | 0.0093 (13) | 0.0115 (12) | −0.0082 (12) |
C6 | 0.0598 (13) | 0.0624 (13) | 0.0503 (11) | −0.0022 (11) | 0.0074 (10) | −0.0002 (9) |
C7 | 0.0794 (16) | 0.0861 (17) | 0.0488 (12) | 0.0087 (14) | 0.0012 (11) | −0.0065 (11) |
C8 | 0.0766 (16) | 0.0900 (18) | 0.0542 (13) | 0.0176 (14) | −0.0051 (12) | 0.0022 (12) |
C9 | 0.0588 (13) | 0.0631 (14) | 0.0527 (11) | 0.0053 (11) | 0.0015 (10) | 0.0023 (10) |
C10 | 0.0672 (15) | 0.0714 (15) | 0.0609 (13) | 0.0158 (12) | −0.0024 (11) | 0.0037 (11) |
C11 | 0.0675 (15) | 0.0668 (14) | 0.0625 (13) | 0.0125 (12) | −0.0072 (11) | −0.0008 (11) |
C12 | 0.0606 (13) | 0.0558 (13) | 0.0572 (12) | 0.0013 (11) | −0.0041 (10) | −0.0027 (10) |
C13 | 0.0774 (16) | 0.0732 (16) | 0.0542 (12) | 0.0107 (13) | −0.0055 (11) | 0.0041 (11) |
C14 | 0.0808 (16) | 0.0790 (16) | 0.0460 (11) | 0.0027 (13) | −0.0001 (11) | −0.0022 (11) |
C15 | 0.0578 (13) | 0.0570 (13) | 0.0506 (11) | −0.0030 (10) | −0.0013 (9) | −0.0058 (9) |
C16 | 0.0729 (16) | 0.0774 (16) | 0.0572 (13) | 0.0066 (13) | 0.0053 (11) | −0.0148 (12) |
C17 | 0.0711 (16) | 0.0721 (16) | 0.0736 (16) | 0.0162 (13) | 0.0046 (13) | −0.0101 (12) |
C18 | 0.0670 (15) | 0.0706 (15) | 0.0666 (14) | 0.0111 (12) | −0.0027 (12) | 0.0004 (12) |
C19 | 0.0580 (13) | 0.0640 (14) | 0.0552 (12) | 0.0043 (11) | −0.0027 (10) | −0.0012 (10) |
C20 | 0.0508 (12) | 0.0509 (12) | 0.0495 (11) | −0.0041 (10) | −0.0010 (9) | −0.0064 (9) |
O1—C2 | 1.350 (2) | C9—N1 | 1.332 (3) |
O1—H1 | 0.8200 | C9—C10 | 1.463 (3) |
N1—N1 | 0.000 (6) | C10—C11 | 1.330 (3) |
N1—C9 | 1.332 (3) | C10—H10 | 0.9300 |
N1—C1 | 1.358 (2) | C11—C12 | 1.468 (3) |
N2—C12 | 1.328 (3) | C11—H11 | 0.9300 |
N2—C20 | 1.366 (2) | C12—C13 | 1.410 (3) |
C1—N1 | 1.358 (2) | C13—C14 | 1.353 (3) |
C1—C2 | 1.413 (3) | C13—H13 | 0.9300 |
C1—C6 | 1.418 (3) | C14—C15 | 1.411 (3) |
C2—C3 | 1.359 (3) | C14—H14 | 0.9300 |
C3—C4 | 1.402 (3) | C15—C16 | 1.405 (3) |
C3—H3 | 0.9300 | C15—C20 | 1.417 (3) |
C4—C5 | 1.354 (3) | C16—C17 | 1.353 (3) |
C4—H4 | 0.9300 | C16—H16 | 0.9300 |
C5—C6 | 1.413 (3) | C17—C18 | 1.403 (3) |
C5—H5 | 0.9300 | C17—H17 | 0.9300 |
C6—C7 | 1.404 (3) | C18—C19 | 1.363 (3) |
C7—C8 | 1.355 (3) | C18—H18 | 0.9300 |
C7—H7 | 0.9300 | C19—C20 | 1.405 (3) |
C8—C9 | 1.416 (3) | C19—H19 | 0.9300 |
C8—H8 | 0.9300 | ||
C2—O1—H1 | 109.5 | N1—C9—C10 | 118.07 (19) |
N1—N1—C9 | 0 (10) | C8—C9—C10 | 120.4 (2) |
N1—N1—C1 | 0 (10) | C11—C10—C9 | 123.5 (2) |
C9—N1—C1 | 118.29 (17) | C11—C10—H10 | 118.2 |
C12—N2—C20 | 117.96 (17) | C9—C10—H10 | 118.2 |
N1—C1—N1 | 0.0 (2) | C10—C11—C12 | 125.2 (2) |
N1—C1—C2 | 117.52 (18) | C10—C11—H11 | 117.4 |
N1—C1—C2 | 117.52 (18) | C12—C11—H11 | 117.4 |
N1—C1—C6 | 123.48 (19) | N2—C12—C13 | 122.4 (2) |
N1—C1—C6 | 123.48 (19) | N2—C12—C11 | 119.03 (19) |
C2—C1—C6 | 119.00 (19) | C13—C12—C11 | 118.5 (2) |
O1—C2—C3 | 120.2 (2) | C14—C13—C12 | 120.2 (2) |
O1—C2—C1 | 119.06 (19) | C14—C13—H13 | 119.9 |
C3—C2—C1 | 120.8 (2) | C12—C13—H13 | 119.9 |
C2—C3—C4 | 119.9 (2) | C13—C14—C15 | 119.4 (2) |
C2—C3—H3 | 120.1 | C13—C14—H14 | 120.3 |
C4—C3—H3 | 120.1 | C15—C14—H14 | 120.3 |
C5—C4—C3 | 121.3 (2) | C16—C15—C14 | 123.7 (2) |
C5—C4—H4 | 119.3 | C16—C15—C20 | 119.1 (2) |
C3—C4—H4 | 119.3 | C14—C15—C20 | 117.19 (19) |
C4—C5—C6 | 120.3 (2) | C17—C16—C15 | 120.6 (2) |
C4—C5—H5 | 119.9 | C17—C16—H16 | 119.7 |
C6—C5—H5 | 119.9 | C15—C16—H16 | 119.7 |
C7—C6—C5 | 124.9 (2) | C16—C17—C18 | 120.5 (2) |
C7—C6—C1 | 116.4 (2) | C16—C17—H17 | 119.7 |
C5—C6—C1 | 118.8 (2) | C18—C17—H17 | 119.7 |
C8—C7—C6 | 120.1 (2) | C19—C18—C17 | 120.4 (2) |
C8—C7—H7 | 119.9 | C19—C18—H18 | 119.8 |
C6—C7—H7 | 119.9 | C17—C18—H18 | 119.8 |
C7—C8—C9 | 120.2 (2) | C18—C19—C20 | 120.4 (2) |
C7—C8—H8 | 119.9 | C18—C19—H19 | 119.8 |
C9—C8—H8 | 119.9 | C20—C19—H19 | 119.8 |
N1—C9—N1 | 0.0 (2) | N2—C20—C19 | 118.30 (17) |
N1—C9—C8 | 121.5 (2) | N2—C20—C15 | 122.76 (18) |
N1—C9—C8 | 121.5 (2) | C19—C20—C15 | 118.94 (19) |
N1—C9—C10 | 118.07 (19) | ||
C9—N1—C1—N1 | 0 (95) | C1—N1—C9—C10 | 177.34 (19) |
N1—N1—C1—C2 | 0.00 (10) | C7—C8—C9—N1 | 1.0 (4) |
C9—N1—C1—C2 | 179.02 (19) | C7—C8—C9—N1 | 1.0 (4) |
N1—N1—C1—C6 | 0.00 (7) | C7—C8—C9—C10 | −175.9 (2) |
C9—N1—C1—C6 | −2.1 (3) | N1—C9—C10—C11 | −6.1 (4) |
N1—C1—C2—O1 | 0.5 (3) | N1—C9—C10—C11 | −6.1 (4) |
N1—C1—C2—O1 | 0.5 (3) | C8—C9—C10—C11 | 171.0 (2) |
C6—C1—C2—O1 | −178.5 (2) | C9—C10—C11—C12 | −174.1 (2) |
N1—C1—C2—C3 | 179.3 (2) | C20—N2—C12—C13 | 0.0 (3) |
N1—C1—C2—C3 | 179.3 (2) | C20—N2—C12—C11 | 178.19 (18) |
C6—C1—C2—C3 | 0.3 (3) | C10—C11—C12—N2 | −11.4 (4) |
O1—C2—C3—C4 | 177.9 (2) | C10—C11—C12—C13 | 166.9 (2) |
C1—C2—C3—C4 | −0.9 (3) | N2—C12—C13—C14 | 0.2 (4) |
C2—C3—C4—C5 | 0.5 (4) | C11—C12—C13—C14 | −177.9 (2) |
C3—C4—C5—C6 | 0.5 (4) | C12—C13—C14—C15 | −0.1 (4) |
C4—C5—C6—C7 | 178.3 (2) | C13—C14—C15—C16 | −179.5 (2) |
C4—C5—C6—C1 | −1.0 (3) | C13—C14—C15—C20 | −0.3 (3) |
N1—C1—C6—C7 | 2.4 (3) | C14—C15—C16—C17 | 178.9 (2) |
N1—C1—C6—C7 | 2.4 (3) | C20—C15—C16—C17 | −0.3 (3) |
C2—C1—C6—C7 | −178.7 (2) | C15—C16—C17—C18 | −0.1 (4) |
N1—C1—C6—C5 | −178.3 (2) | C16—C17—C18—C19 | 0.6 (4) |
N1—C1—C6—C5 | −178.3 (2) | C17—C18—C19—C20 | −0.8 (3) |
C2—C1—C6—C5 | 0.6 (3) | C12—N2—C20—C19 | 179.18 (19) |
C5—C6—C7—C8 | 179.7 (2) | C12—N2—C20—C15 | −0.5 (3) |
C1—C6—C7—C8 | −0.9 (3) | C18—C19—C20—N2 | −179.32 (19) |
C6—C7—C8—C9 | −0.7 (4) | C18—C19—C20—C15 | 0.3 (3) |
C1—N1—C9—N1 | 0 (58) | C16—C15—C20—N2 | 179.8 (2) |
N1—N1—C9—C8 | 0.00 (9) | C14—C15—C20—N2 | 0.6 (3) |
C1—N1—C9—C8 | 0.3 (3) | C16—C15—C20—C19 | 0.2 (3) |
N1—N1—C9—C10 | 0.00 (9) | C14—C15—C20—C19 | −179.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 2.23 | 2.696 (2) | 116 |
O1—H1···N2i | 0.82 | 2.49 | 3.099 (2) | 133 |
Symmetry code: (i) y+1/4, −x+5/4, z+1/4. |
C20H14N2O | F(000) = 624 |
Mr = 298.33 | Dx = 1.311 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2yn | Cell parameters from 2512 reflections |
a = 10.7240 (6) Å | θ = 2.5–25.1° |
b = 8.9019 (5) Å | µ = 0.08 mm−1 |
c = 16.1894 (8) Å | T = 298 K |
β = 102.039 (4)° | Block, yellow |
V = 1511.51 (14) Å3 | 0.32 × 0.29 × 0.28 mm |
Z = 4 |
CCD area detector diffractometer | 2376 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 27.6°, θmin = 2.1° |
phi and ω scans | h = −10→13 |
13247 measured reflections | k = −11→10 |
3460 independent reflections | l = −21→20 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0526P)2 + 0.1209P] where P = (Fo2 + 2Fc2)/3 |
3460 reflections | (Δ/σ)max < 0.001 |
209 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C20H14N2O | V = 1511.51 (14) Å3 |
Mr = 298.33 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.7240 (6) Å | µ = 0.08 mm−1 |
b = 8.9019 (5) Å | T = 298 K |
c = 16.1894 (8) Å | 0.32 × 0.29 × 0.28 mm |
β = 102.039 (4)° |
CCD area detector diffractometer | 2376 reflections with I > 2σ(I) |
13247 measured reflections | Rint = 0.033 |
3460 independent reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.12 e Å−3 |
3460 reflections | Δρmin = −0.19 e Å−3 |
209 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 | ||
O1 | 0.28263 (10) | 0.49707 (12) | 0.16643 (7) | 0.0578 (3) | |
H1 | 0.3032 | 0.5676 | 0.1396 | 0.087* | |
N1 | 0.50709 (11) | 0.55344 (13) | 0.11577 (7) | 0.0430 (3) | |
N2 | 0.74000 (12) | 1.22073 (14) | −0.08230 (7) | 0.0502 (3) | |
C1 | 0.49795 (13) | 0.42565 (15) | 0.16041 (8) | 0.0417 (3) | |
C2 | 0.38159 (14) | 0.40009 (16) | 0.18676 (9) | 0.0464 (3) | |
C3 | 0.36949 (16) | 0.27616 (18) | 0.23504 (9) | 0.0558 (4) | |
H3 | 0.2938 | 0.2600 | 0.2531 | 0.067* | |
C4 | 0.46986 (18) | 0.17414 (18) | 0.25717 (10) | 0.0608 (4) | |
H4 | 0.4600 | 0.0912 | 0.2901 | 0.073* | |
C5 | 0.58216 (17) | 0.19378 (17) | 0.23135 (9) | 0.0568 (4) | |
H5 | 0.6474 | 0.1238 | 0.2459 | 0.068* | |
C6 | 0.59899 (14) | 0.32088 (15) | 0.18237 (9) | 0.0464 (3) | |
C7 | 0.71088 (15) | 0.35195 (17) | 0.15318 (10) | 0.0538 (4) | |
H7 | 0.7789 | 0.2850 | 0.1642 | 0.065* | |
C8 | 0.71976 (14) | 0.47981 (16) | 0.10877 (10) | 0.0513 (4) | |
H8 | 0.7937 | 0.5004 | 0.0894 | 0.062* | |
C9 | 0.61637 (13) | 0.58097 (15) | 0.09222 (9) | 0.0431 (3) | |
C10 | 0.62348 (14) | 0.72455 (16) | 0.04910 (9) | 0.0465 (3) | |
H10 | 0.5472 | 0.7652 | 0.0196 | 0.056* | |
C11 | 0.72883 (14) | 0.80146 (15) | 0.04840 (9) | 0.0463 (3) | |
H11 | 0.8056 | 0.7607 | 0.0771 | 0.056* | |
C12 | 0.73372 (13) | 0.94639 (15) | 0.00569 (8) | 0.0421 (3) | |
C13 | 0.64171 (15) | 0.98503 (17) | −0.06289 (10) | 0.0510 (4) | |
H13 | 0.5743 | 0.9198 | −0.0823 | 0.061* | |
C14 | 0.64829 (15) | 1.12191 (18) | −0.10403 (10) | 0.0541 (4) | |
H14 | 0.5832 | 1.1445 | −0.1500 | 0.065* | |
C15 | 0.83499 (13) | 1.18596 (15) | −0.01465 (9) | 0.0431 (3) | |
C16 | 0.93575 (15) | 1.28937 (16) | 0.00899 (10) | 0.0519 (4) | |
H16 | 0.9369 | 1.3767 | −0.0224 | 0.062* | |
C17 | 1.03098 (15) | 1.26297 (18) | 0.07688 (11) | 0.0589 (4) | |
H17 | 1.0966 | 1.3323 | 0.0919 | 0.071* | |
C18 | 1.03080 (15) | 1.13168 (19) | 0.12437 (11) | 0.0598 (4) | |
H18 | 1.0961 | 1.1149 | 0.1712 | 0.072* | |
C19 | 0.93615 (14) | 1.02835 (17) | 0.10280 (10) | 0.0511 (4) | |
H19 | 0.9378 | 0.9416 | 0.1350 | 0.061* | |
C20 | 0.83558 (12) | 1.05068 (14) | 0.03233 (8) | 0.0405 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0494 (6) | 0.0559 (6) | 0.0713 (7) | −0.0055 (5) | 0.0198 (5) | 0.0106 (5) |
N1 | 0.0423 (6) | 0.0407 (6) | 0.0451 (6) | −0.0055 (5) | 0.0074 (5) | 0.0011 (5) |
N2 | 0.0531 (7) | 0.0470 (7) | 0.0514 (7) | −0.0005 (6) | 0.0127 (6) | 0.0067 (6) |
C1 | 0.0478 (8) | 0.0376 (7) | 0.0379 (7) | −0.0084 (6) | 0.0049 (6) | −0.0026 (6) |
C2 | 0.0509 (9) | 0.0445 (8) | 0.0429 (7) | −0.0106 (7) | 0.0080 (6) | −0.0026 (6) |
C3 | 0.0658 (10) | 0.0547 (9) | 0.0477 (8) | −0.0169 (8) | 0.0140 (8) | 0.0011 (7) |
C4 | 0.0851 (12) | 0.0464 (9) | 0.0479 (9) | −0.0158 (9) | 0.0070 (9) | 0.0066 (7) |
C5 | 0.0707 (11) | 0.0432 (8) | 0.0503 (9) | −0.0018 (8) | −0.0016 (8) | 0.0044 (7) |
C6 | 0.0539 (9) | 0.0393 (7) | 0.0428 (7) | −0.0044 (7) | 0.0025 (6) | −0.0031 (6) |
C7 | 0.0527 (9) | 0.0419 (8) | 0.0645 (10) | 0.0047 (7) | 0.0066 (8) | −0.0041 (7) |
C8 | 0.0459 (8) | 0.0449 (8) | 0.0652 (10) | −0.0020 (7) | 0.0167 (7) | −0.0059 (7) |
C9 | 0.0453 (8) | 0.0391 (7) | 0.0446 (7) | −0.0062 (6) | 0.0086 (6) | −0.0029 (6) |
C10 | 0.0457 (8) | 0.0433 (8) | 0.0513 (8) | −0.0005 (6) | 0.0119 (7) | 0.0021 (6) |
C11 | 0.0458 (8) | 0.0424 (8) | 0.0508 (8) | −0.0035 (6) | 0.0102 (7) | 0.0018 (6) |
C12 | 0.0430 (8) | 0.0403 (7) | 0.0451 (7) | −0.0019 (6) | 0.0143 (6) | −0.0015 (6) |
C13 | 0.0503 (8) | 0.0510 (9) | 0.0503 (8) | −0.0096 (7) | 0.0074 (7) | 0.0016 (7) |
C14 | 0.0542 (9) | 0.0564 (9) | 0.0488 (8) | −0.0016 (8) | 0.0041 (7) | 0.0064 (7) |
C15 | 0.0428 (8) | 0.0397 (7) | 0.0496 (8) | 0.0015 (6) | 0.0157 (6) | −0.0001 (6) |
C16 | 0.0529 (9) | 0.0399 (8) | 0.0664 (10) | −0.0045 (7) | 0.0202 (8) | 0.0030 (7) |
C17 | 0.0494 (9) | 0.0481 (9) | 0.0788 (11) | −0.0121 (7) | 0.0124 (8) | −0.0031 (8) |
C18 | 0.0493 (9) | 0.0572 (10) | 0.0674 (10) | −0.0059 (8) | −0.0004 (8) | 0.0012 (8) |
C19 | 0.0476 (8) | 0.0465 (8) | 0.0577 (9) | −0.0020 (7) | 0.0075 (7) | 0.0052 (7) |
C20 | 0.0400 (7) | 0.0373 (7) | 0.0462 (8) | −0.0004 (6) | 0.0133 (6) | −0.0015 (6) |
O1—C2 | 1.3543 (18) | C9—C10 | 1.4660 (19) |
O1—H1 | 0.8200 | C10—C11 | 1.323 (2) |
N1—C9 | 1.3286 (18) | C10—H10 | 0.9300 |
N1—C1 | 1.3621 (17) | C11—C12 | 1.4699 (19) |
N2—C14 | 1.3117 (19) | C11—H11 | 0.9300 |
N2—C15 | 1.3667 (18) | C12—C13 | 1.367 (2) |
C1—C6 | 1.418 (2) | C12—C20 | 1.4299 (19) |
C1—C2 | 1.419 (2) | C13—C14 | 1.397 (2) |
C2—C3 | 1.374 (2) | C13—H13 | 0.9300 |
C3—C4 | 1.397 (2) | C14—H14 | 0.9300 |
C3—H3 | 0.9300 | C15—C16 | 1.410 (2) |
C4—C5 | 1.366 (2) | C15—C20 | 1.4236 (19) |
C4—H4 | 0.9300 | C16—C17 | 1.356 (2) |
C5—C6 | 1.415 (2) | C16—H16 | 0.9300 |
C5—H5 | 0.9300 | C17—C18 | 1.399 (2) |
C6—C7 | 1.406 (2) | C17—H17 | 0.9300 |
C7—C8 | 1.360 (2) | C18—C19 | 1.360 (2) |
C7—H7 | 0.9300 | C18—H18 | 0.9300 |
C8—C9 | 1.410 (2) | C19—C20 | 1.411 (2) |
C8—H8 | 0.9300 | C19—H19 | 0.9300 |
C2—O1—H1 | 109.5 | C9—C10—H10 | 117.1 |
C9—N1—C1 | 118.14 (12) | C10—C11—C12 | 124.92 (14) |
C14—N2—C15 | 117.06 (12) | C10—C11—H11 | 117.5 |
N1—C1—C6 | 123.14 (13) | C12—C11—H11 | 117.5 |
N1—C1—C2 | 117.29 (13) | C13—C12—C20 | 117.28 (12) |
C6—C1—C2 | 119.55 (13) | C13—C12—C11 | 120.83 (13) |
O1—C2—C3 | 119.20 (14) | C20—C12—C11 | 121.87 (12) |
O1—C2—C1 | 121.23 (12) | C12—C13—C14 | 120.47 (14) |
C3—C2—C1 | 119.56 (14) | C12—C13—H13 | 119.8 |
C2—C3—C4 | 120.59 (15) | C14—C13—H13 | 119.8 |
C2—C3—H3 | 119.7 | N2—C14—C13 | 124.50 (14) |
C4—C3—H3 | 119.7 | N2—C14—H14 | 117.7 |
C5—C4—C3 | 121.31 (15) | C13—C14—H14 | 117.7 |
C5—C4—H4 | 119.3 | N2—C15—C16 | 118.06 (13) |
C3—C4—H4 | 119.3 | N2—C15—C20 | 122.63 (12) |
C4—C5—C6 | 119.84 (15) | C16—C15—C20 | 119.30 (13) |
C4—C5—H5 | 120.1 | C17—C16—C15 | 120.78 (14) |
C6—C5—H5 | 120.1 | C17—C16—H16 | 119.6 |
C7—C6—C5 | 124.30 (15) | C15—C16—H16 | 119.6 |
C7—C6—C1 | 116.59 (13) | C16—C17—C18 | 120.21 (14) |
C5—C6—C1 | 119.12 (14) | C16—C17—H17 | 119.9 |
C8—C7—C6 | 120.08 (14) | C18—C17—H17 | 119.9 |
C8—C7—H7 | 120.0 | C19—C18—C17 | 120.68 (15) |
C6—C7—H7 | 120.0 | C19—C18—H18 | 119.7 |
C7—C8—C9 | 119.73 (14) | C17—C18—H18 | 119.7 |
C7—C8—H8 | 120.1 | C18—C19—C20 | 121.05 (14) |
C9—C8—H8 | 120.1 | C18—C19—H19 | 119.5 |
N1—C9—C8 | 122.23 (13) | C20—C19—H19 | 119.5 |
N1—C9—C10 | 115.73 (12) | C19—C20—C15 | 117.94 (12) |
C8—C9—C10 | 122.03 (13) | C19—C20—C12 | 124.01 (12) |
C11—C10—C9 | 125.77 (14) | C15—C20—C12 | 118.04 (12) |
C11—C10—H10 | 117.1 | ||
C9—N1—C1—C6 | −0.34 (19) | C9—C10—C11—C12 | −179.12 (13) |
C9—N1—C1—C2 | 178.49 (12) | C10—C11—C12—C13 | −26.6 (2) |
N1—C1—C2—O1 | 1.63 (19) | C10—C11—C12—C20 | 155.01 (14) |
C6—C1—C2—O1 | −179.49 (12) | C20—C12—C13—C14 | −0.4 (2) |
N1—C1—C2—C3 | −177.22 (12) | C11—C12—C13—C14 | −178.87 (13) |
C6—C1—C2—C3 | 1.7 (2) | C15—N2—C14—C13 | 0.0 (2) |
O1—C2—C3—C4 | −179.91 (13) | C12—C13—C14—N2 | 0.9 (2) |
C1—C2—C3—C4 | −1.0 (2) | C14—N2—C15—C16 | 178.94 (14) |
C2—C3—C4—C5 | −0.3 (2) | C14—N2—C15—C20 | −1.2 (2) |
C3—C4—C5—C6 | 1.1 (2) | N2—C15—C16—C17 | 178.27 (14) |
C4—C5—C6—C7 | 179.56 (14) | C20—C15—C16—C17 | −1.6 (2) |
C4—C5—C6—C1 | −0.4 (2) | C15—C16—C17—C18 | 0.3 (2) |
N1—C1—C6—C7 | −2.10 (19) | C16—C17—C18—C19 | 0.6 (3) |
C2—C1—C6—C7 | 179.09 (13) | C17—C18—C19—C20 | −0.2 (3) |
N1—C1—C6—C5 | 177.87 (12) | C18—C19—C20—C15 | −1.1 (2) |
C2—C1—C6—C5 | −0.93 (19) | C18—C19—C20—C12 | 179.48 (14) |
C5—C6—C7—C8 | −177.81 (14) | N2—C15—C20—C19 | −177.91 (13) |
C1—C6—C7—C8 | 2.2 (2) | C16—C15—C20—C19 | 1.95 (19) |
C6—C7—C8—C9 | 0.0 (2) | N2—C15—C20—C12 | 1.56 (19) |
C1—N1—C9—C8 | 2.76 (19) | C16—C15—C20—C12 | −178.57 (13) |
C1—N1—C9—C10 | −176.27 (12) | C13—C12—C20—C19 | 178.75 (13) |
C7—C8—C9—N1 | −2.7 (2) | C11—C12—C20—C19 | −2.8 (2) |
C7—C8—C9—C10 | 176.30 (14) | C13—C12—C20—C15 | −0.69 (19) |
N1—C9—C10—C11 | 152.78 (15) | C11—C12—C20—C15 | 177.74 (12) |
C8—C9—C10—C11 | −26.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2i | 0.82 | 2.11 | 2.8438 (15) | 149 |
O1—H1···N1 | 0.82 | 2.30 | 2.7463 (16) | 115 |
Symmetry code: (i) −x+1, −y+2, −z. |
Experimental details
(3a) | (3b) | |
Crystal data | ||
Chemical formula | C20H14N2O | C20H14N2O |
Mr | 298.33 | 298.33 |
Crystal system, space group | Tetragonal, I41/a | Monoclinic, P21/n |
Temperature (K) | 298 | 298 |
a, b, c (Å) | 21.5111 (7), 21.5111 (7), 13.2377 (9) | 10.7240 (6), 8.9019 (5), 16.1894 (8) |
α, β, γ (°) | 90, 90, 90 | 90, 102.039 (4), 90 |
V (Å3) | 6125.4 (5) | 1511.51 (14) |
Z | 16 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.08 | 0.08 |
Crystal size (mm) | 0.16 × 0.13 × 0.10 | 0.32 × 0.29 × 0.28 |
Data collection | ||
Diffractometer | CCD area detector diffractometer | CCD area detector diffractometer |
Absorption correction | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25513, 3576, 1932 | 13247, 3460, 2376 |
Rint | 0.057 | 0.033 |
(sin θ/λ)max (Å−1) | 0.653 | 0.651 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.168, 1.00 | 0.043, 0.116, 1.05 |
No. of reflections | 3576 | 3460 |
No. of parameters | 209 | 209 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.48, −0.19 | 0.12, −0.19 |
Computer programs: Bruker SMART, Bruker SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), Bruker SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 2.23 | 2.696 (2) | 116.1 |
O1—H1···N2i | 0.82 | 2.49 | 3.099 (2) | 132.5 |
Symmetry code: (i) y+1/4, −x+5/4, z+1/4. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2i | 0.82 | 2.11 | 2.8438 (15) | 149.2 |
O1—H1···N1 | 0.82 | 2.301 | 2.7463 (16) | 114.63 |
Symmetry code: (i) −x+1, −y+2, −z. |