Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801020049/ci6079sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801020049/ci6079Isup2.hkl |
CCDC reference: 164867
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.
C24H18N10O | Z = 2 |
Mr = 462.48 | F(000) = 480 |
Triclinic, P1 | Dx = 1.426 Mg m−3 |
a = 7.949 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.540 (7) Å | Cell parameters from 4426 reflections |
c = 12.118 (7) Å | θ = 2.4–25.0° |
α = 83.200 (11)° | µ = 0.10 mm−1 |
β = 85.971 (12)° | T = 293 K |
γ = 77.557 (11)° | Prism, orange |
V = 1076.8 (11) Å3 | 0.30 × 0.25 × 0.20 mm |
Bruker SMART 1000 diffractometer | 2474 reflections with I > 2σ(I) |
ω scans | Rint = 0.052 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1997) | θmax = 25.0° |
Tmin = 0.972, Tmax = 0.981 | h = −8→9 |
4478 measured reflections | k = −13→13 |
3752 independent reflections | l = −7→14 |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.056 | w = 1/[σ2(Fo2) + (0.005P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.086 | (Δ/σ)max = 0.008 |
S = 0.88 | Δρmax = 0.17 e Å−3 |
3752 reflections | Δρmin = −0.17 e Å−3 |
324 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. Full-matrix |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2283 (3) | 0.8551 (2) | 0.36396 (17) | 0.0493 (7) | |
N1 | 0.5403 (4) | 0.8270 (3) | 0.5674 (2) | 0.0504 (9) | |
N2 | 0.7841 (4) | 0.5854 (2) | 0.0521 (2) | 0.0402 (8) | |
N3 | 1.2522 (4) | 0.5890 (3) | 0.4852 (2) | 0.0459 (9) | |
N4 | 0.7594 (4) | 0.9077 (3) | 0.0661 (2) | 0.0521 (9) | |
N5 | 0.8204 (4) | 0.6993 (2) | 0.2322 (2) | 0.0345 (8) | |
N6 | 0.8597 (4) | 0.6899 (3) | 0.3460 (2) | 0.0380 (8) | |
N7 | 1.1443 (4) | 0.6330 (3) | 0.2762 (2) | 0.0428 (8) | |
H7 | 1.2536 (18) | 0.629 (3) | 0.294 (2) | 0.048 (12)* | |
N8 | 1.1060 (4) | 0.7091 (3) | 0.1759 (2) | 0.0421 (8) | |
N9 | 0.5108 (4) | 0.7225 (2) | 0.2625 (2) | 0.0390 (8) | |
N10 | 0.5166 (4) | 0.7678 (3) | 0.3631 (2) | 0.0431 (9) | |
H10 | 0.614 (2) | 0.766 (3) | 0.397 (2) | 0.054 (13)* | |
C1 | 1.3134 (5) | 0.5693 (3) | 0.5886 (3) | 0.0530 (11) | |
H1 | 1.4303 | 0.5374 | 0.5964 | 0.064* | |
C2 | 1.2123 (6) | 0.5938 (3) | 0.6822 (3) | 0.0568 (12) | |
H2 | 1.2602 | 0.5812 | 0.7516 | 0.068* | |
C3 | 1.0394 (6) | 0.6372 (4) | 0.6723 (3) | 0.0575 (12) | |
H3 | 0.9676 | 0.6513 | 0.7354 | 0.069* | |
C4 | 0.9712 (5) | 0.6603 (3) | 0.5676 (3) | 0.0520 (11) | |
H4 | 0.8545 | 0.6916 | 0.5583 | 0.062* | |
C5 | 1.0853 (5) | 0.6344 (3) | 0.4777 (3) | 0.0371 (10) | |
C6 | 1.0189 (5) | 0.6554 (3) | 0.3626 (3) | 0.0369 (10) | |
C7 | 0.9463 (5) | 0.7364 (3) | 0.1557 (3) | 0.0318 (9) | |
C8 | 0.8946 (5) | 0.8195 (3) | 0.0548 (3) | 0.0381 (10) | |
C9 | 0.9952 (5) | 0.8068 (4) | −0.0425 (3) | 0.0623 (13) | |
H9 | 1.0897 | 0.7437 | −0.0470 | 0.075* | |
C10 | 0.9519 (6) | 0.8903 (5) | −0.1333 (3) | 0.0706 (14) | |
H10A | 1.0149 | 0.8829 | −0.2006 | 0.085* | |
C11 | 0.8170 (7) | 0.9826 (4) | −0.1228 (3) | 0.0733 (15) | |
H11 | 0.7885 | 1.0421 | −0.1812 | 0.088* | |
C12 | 0.7232 (6) | 0.9860 (4) | −0.0234 (4) | 0.0740 (14) | |
H12 | 0.6270 | 1.0477 | −0.0181 | 0.089* | |
C13 | 0.7754 (5) | 0.5528 (3) | −0.0498 (3) | 0.0454 (11) | |
H13 | 0.8716 | 0.5026 | −0.0789 | 0.054* | |
C14 | 0.6339 (5) | 0.5887 (3) | −0.1136 (3) | 0.0487 (11) | |
H14 | 0.6360 | 0.5657 | −0.1848 | 0.058* | |
C15 | 0.4882 (5) | 0.6599 (3) | −0.0696 (3) | 0.0512 (11) | |
H15 | 0.3894 | 0.6851 | −0.1101 | 0.061* | |
C16 | 0.4923 (4) | 0.6928 (3) | 0.0358 (3) | 0.0388 (10) | |
H16 | 0.3953 | 0.7394 | 0.0680 | 0.047* | |
C17 | 0.6416 (5) | 0.6559 (3) | 0.0926 (3) | 0.0310 (9) | |
C18 | 0.6535 (5) | 0.6968 (3) | 0.2050 (3) | 0.0336 (9) | |
C19 | 0.3687 (5) | 0.8305 (3) | 0.4076 (3) | 0.0401 (10) | |
C20 | 0.3867 (5) | 0.8703 (3) | 0.5199 (3) | 0.0387 (10) | |
C21 | 0.2542 (5) | 0.9475 (3) | 0.5661 (3) | 0.0532 (12) | |
H21 | 0.1510 | 0.9749 | 0.5305 | 0.064* | |
C22 | 0.2774 (6) | 0.9844 (4) | 0.6680 (3) | 0.0653 (14) | |
H22 | 0.1898 | 1.0375 | 0.7019 | 0.078* | |
C23 | 0.4312 (7) | 0.9414 (4) | 0.7178 (3) | 0.0675 (14) | |
H23 | 0.4482 | 0.9638 | 0.7867 | 0.081* | |
C24 | 0.5592 (6) | 0.8655 (4) | 0.6656 (3) | 0.0674 (14) | |
H24 | 0.6641 | 0.8391 | 0.6993 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0435 (19) | 0.0626 (19) | 0.0394 (16) | −0.0068 (16) | −0.0033 (13) | −0.0025 (13) |
N1 | 0.060 (3) | 0.060 (2) | 0.032 (2) | −0.012 (2) | 0.0011 (17) | −0.0101 (17) |
N2 | 0.037 (2) | 0.049 (2) | 0.0304 (19) | 0.0017 (17) | 0.0008 (15) | −0.0083 (16) |
N3 | 0.042 (2) | 0.056 (2) | 0.036 (2) | −0.0047 (18) | −0.0120 (16) | 0.0052 (16) |
N4 | 0.060 (2) | 0.041 (2) | 0.045 (2) | 0.0055 (19) | −0.0060 (17) | 0.0048 (17) |
N5 | 0.036 (2) | 0.052 (2) | 0.0168 (17) | −0.0111 (17) | −0.0026 (14) | −0.0024 (14) |
N6 | 0.037 (2) | 0.055 (2) | 0.0212 (17) | −0.0080 (18) | −0.0065 (14) | −0.0015 (14) |
N7 | 0.035 (2) | 0.063 (2) | 0.0247 (19) | 0.000 (2) | −0.0013 (16) | −0.0008 (16) |
N8 | 0.041 (2) | 0.059 (2) | 0.0239 (18) | −0.0077 (18) | 0.0012 (15) | −0.0011 (15) |
N9 | 0.039 (2) | 0.054 (2) | 0.0242 (18) | −0.0100 (17) | 0.0015 (14) | −0.0061 (15) |
N10 | 0.037 (2) | 0.065 (2) | 0.027 (2) | −0.007 (2) | 0.0012 (16) | −0.0144 (16) |
C1 | 0.050 (3) | 0.061 (3) | 0.047 (3) | −0.010 (2) | −0.017 (2) | 0.006 (2) |
C2 | 0.086 (4) | 0.058 (3) | 0.029 (3) | −0.019 (3) | −0.015 (2) | 0.003 (2) |
C3 | 0.064 (3) | 0.076 (3) | 0.032 (3) | −0.014 (3) | −0.003 (2) | −0.004 (2) |
C4 | 0.048 (3) | 0.070 (3) | 0.034 (3) | −0.003 (2) | −0.009 (2) | −0.004 (2) |
C5 | 0.045 (3) | 0.043 (2) | 0.024 (2) | −0.012 (2) | −0.0045 (19) | −0.0020 (18) |
C6 | 0.042 (3) | 0.040 (2) | 0.027 (2) | −0.008 (2) | −0.0030 (19) | −0.0013 (17) |
C7 | 0.027 (2) | 0.040 (2) | 0.029 (2) | −0.005 (2) | −0.0029 (17) | −0.0096 (17) |
C8 | 0.038 (3) | 0.046 (3) | 0.030 (2) | −0.008 (2) | −0.0035 (18) | −0.0044 (19) |
C9 | 0.062 (3) | 0.090 (3) | 0.033 (3) | −0.015 (3) | 0.009 (2) | −0.006 (2) |
C10 | 0.090 (4) | 0.094 (4) | 0.032 (3) | −0.042 (3) | 0.004 (3) | 0.010 (3) |
C11 | 0.100 (4) | 0.070 (4) | 0.053 (3) | −0.035 (3) | −0.021 (3) | 0.024 (3) |
C12 | 0.088 (4) | 0.045 (3) | 0.081 (4) | −0.004 (3) | −0.020 (3) | 0.017 (3) |
C13 | 0.047 (3) | 0.048 (3) | 0.042 (3) | −0.006 (2) | 0.002 (2) | −0.016 (2) |
C14 | 0.052 (3) | 0.062 (3) | 0.034 (2) | −0.009 (2) | −0.005 (2) | −0.017 (2) |
C15 | 0.043 (3) | 0.072 (3) | 0.036 (2) | −0.004 (2) | −0.0082 (19) | −0.009 (2) |
C16 | 0.032 (2) | 0.044 (3) | 0.038 (2) | −0.001 (2) | −0.0007 (18) | −0.0106 (19) |
C17 | 0.033 (2) | 0.035 (2) | 0.025 (2) | −0.007 (2) | 0.0000 (17) | −0.0039 (17) |
C18 | 0.031 (2) | 0.042 (2) | 0.026 (2) | −0.007 (2) | −0.0043 (17) | 0.0042 (17) |
C19 | 0.039 (3) | 0.044 (3) | 0.036 (2) | −0.007 (2) | 0.000 (2) | −0.0026 (19) |
C20 | 0.049 (3) | 0.035 (2) | 0.031 (2) | −0.010 (2) | 0.006 (2) | −0.0043 (18) |
C21 | 0.054 (3) | 0.053 (3) | 0.049 (3) | −0.001 (2) | 0.007 (2) | −0.011 (2) |
C22 | 0.086 (4) | 0.058 (3) | 0.053 (3) | −0.019 (3) | 0.024 (3) | −0.022 (3) |
C23 | 0.100 (4) | 0.077 (4) | 0.030 (3) | −0.026 (3) | 0.007 (3) | −0.017 (2) |
C24 | 0.079 (4) | 0.082 (4) | 0.039 (3) | −0.009 (3) | −0.003 (2) | −0.017 (2) |
O1—C19 | 1.232 (4) | C5—C6 | 1.500 (4) |
N1—C24 | 1.347 (4) | C7—C8 | 1.486 (4) |
N1—C20 | 1.356 (4) | C8—C9 | 1.382 (4) |
N2—C13 | 1.343 (3) | C9—C10 | 1.384 (5) |
N2—C17 | 1.344 (4) | C9—H9 | 0.93 |
N3—C5 | 1.322 (4) | C10—C11 | 1.349 (5) |
N3—C1 | 1.353 (4) | C10—H10A | 0.93 |
N4—C8 | 1.323 (4) | C11—C12 | 1.371 (5) |
N4—C12 | 1.333 (4) | C11—H11 | 0.93 |
N5—C18 | 1.396 (4) | C12—H12 | 0.93 |
N5—C7 | 1.416 (4) | C13—C14 | 1.371 (4) |
N5—N6 | 1.422 (3) | C13—H13 | 0.93 |
N6—C6 | 1.265 (4) | C14—C15 | 1.382 (4) |
N7—C6 | 1.401 (4) | C14—H14 | 0.93 |
N7—N8 | 1.423 (4) | C15—C16 | 1.379 (4) |
N7—H7 | 0.899 (10) | C15—H15 | 0.93 |
N8—C7 | 1.274 (4) | C16—C17 | 1.375 (4) |
N9—C18 | 1.285 (4) | C16—H16 | 0.93 |
N9—N10 | 1.389 (3) | C17—C18 | 1.509 (4) |
N10—C19 | 1.355 (4) | C19—C20 | 1.512 (4) |
N10—H10 | 0.896 (10) | C20—C21 | 1.360 (4) |
C1—C2 | 1.364 (4) | C21—C22 | 1.389 (5) |
C1—H1 | 0.93 | C21—H21 | 0.93 |
C2—C3 | 1.366 (5) | C22—C23 | 1.370 (5) |
C2—H2 | 0.93 | C22—H22 | 0.93 |
C3—C4 | 1.388 (4) | C23—C24 | 1.363 (5) |
C3—H3 | 0.93 | C23—H23 | 0.93 |
C4—C5 | 1.386 (4) | C24—H24 | 0.93 |
C4—H4 | 0.93 | ||
C24—N1—C20 | 116.5 (3) | C11—C10—H10A | 120.4 |
C13—N2—C17 | 116.3 (3) | C9—C10—H10A | 120.4 |
C5—N3—C1 | 116.5 (3) | C10—C11—C12 | 118.1 (4) |
C8—N4—C12 | 115.9 (3) | C10—C11—H11 | 121.0 |
C18—N5—C7 | 124.3 (3) | C12—C11—H11 | 121.0 |
C18—N5—N6 | 119.3 (3) | N4—C12—C11 | 125.0 (4) |
C7—N5—N6 | 114.9 (3) | N4—C12—H12 | 117.5 |
C6—N6—N5 | 113.5 (3) | C11—C12—H12 | 117.5 |
C6—N7—N8 | 114.1 (3) | N2—C13—C14 | 124.3 (3) |
C6—N7—H7 | 115.8 (19) | N2—C13—H13 | 117.9 |
N8—N7—H7 | 110 (2) | C14—C13—H13 | 117.9 |
C7—N8—N7 | 114.1 (3) | C13—C14—C15 | 118.3 (3) |
C18—N9—N10 | 117.2 (3) | C13—C14—H14 | 120.8 |
C19—N10—N9 | 118.4 (3) | C15—C14—H14 | 120.8 |
C19—N10—H10 | 116 (2) | C16—C15—C14 | 118.6 (3) |
N9—N10—H10 | 125 (2) | C16—C15—H15 | 120.7 |
N3—C1—C2 | 123.3 (4) | C14—C15—H15 | 120.7 |
N3—C1—H1 | 118.3 | C17—C16—C15 | 119.2 (3) |
C2—C1—H1 | 118.3 | C17—C16—H16 | 120.4 |
C1—C2—C3 | 118.8 (4) | C15—C16—H16 | 120.4 |
C1—C2—H2 | 120.6 | N2—C17—C16 | 123.2 (3) |
C3—C2—H2 | 120.6 | N2—C17—C18 | 116.3 (3) |
C2—C3—C4 | 119.8 (4) | C16—C17—C18 | 120.4 (3) |
C2—C3—H3 | 120.1 | N9—C18—N5 | 129.3 (3) |
C4—C3—H3 | 120.1 | N9—C18—C17 | 116.1 (3) |
C5—C4—C3 | 116.9 (4) | N5—C18—C17 | 114.5 (3) |
C5—C4—H4 | 121.6 | O1—C19—N10 | 125.1 (3) |
C3—C4—H4 | 121.6 | O1—C19—C20 | 120.6 (3) |
N3—C5—C4 | 124.6 (3) | N10—C19—C20 | 114.3 (3) |
N3—C5—C6 | 116.0 (3) | N1—C20—C21 | 123.9 (4) |
C4—C5—C6 | 119.4 (4) | N1—C20—C19 | 116.3 (3) |
N6—C6—N7 | 122.8 (3) | C21—C20—C19 | 119.8 (4) |
N6—C6—C5 | 121.6 (3) | C20—C21—C22 | 118.1 (4) |
N7—C6—C5 | 115.6 (3) | C20—C21—H21 | 120.9 |
N8—C7—N5 | 121.4 (3) | C22—C21—H21 | 120.9 |
N8—C7—C8 | 117.5 (3) | C23—C22—C21 | 119.0 (4) |
N5—C7—C8 | 120.7 (3) | C23—C22—H22 | 120.5 |
N4—C8—C9 | 123.5 (3) | C21—C22—H22 | 120.5 |
N4—C8—C7 | 117.0 (3) | C24—C23—C22 | 119.5 (4) |
C9—C8—C7 | 119.3 (4) | C24—C23—H23 | 120.2 |
C8—C9—C10 | 118.3 (4) | C22—C23—H23 | 120.2 |
C8—C9—H9 | 120.8 | N1—C24—C23 | 122.9 (4) |
C10—C9—H9 | 120.8 | N1—C24—H24 | 118.5 |
C11—C10—C9 | 119.2 (4) | C23—C24—H24 | 118.5 |