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
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.056
- wR factor = 0.086
- Data-to-parameter ratio = 11.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level A:
DIFF_020 Alert A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards.
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
0 Alert Level C = Please check
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 |
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