Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016946/wk6050sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016946/wk6050Isup2.hkl |
CCDC reference: 277801
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).
C24H19N3O2 | F(000) = 1600 |
Mr = 381.42 | Dx = 1.272 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 4326 reflections |
a = 9.801 (3) Å | θ = 2.6–27.0° |
b = 15.549 (4) Å | µ = 0.08 mm−1 |
c = 26.142 (7) Å | T = 273 K |
V = 3984.1 (19) Å3 | Block, colorless |
Z = 8 | 0.48 × 0.37 × 0.32 mm |
Bruker SMART CCD 1K area-detector diffractometer | 2563 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.041 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 27.1°, θmin = 2.6° |
Tmin = 0.961, Tmax = 0.974 | h = −12→12 |
17659 measured reflections | k = −19→19 |
4326 independent reflections | l = −33→18 |
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Only H-atom displacement parameters refined |
R[F2 > 2σ(F2)] = 0.054 | w = 1/[σ2(Fo2) + (0.0634P)2 + 2.2522P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.130 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.38 e Å−3 |
4326 reflections | Δρmin = −0.56 e Å−3 |
261 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | −0.1756 (2) | 0.30445 (13) | 0.00221 (6) | 0.0669 (6) | |
O2A | 0.5881 (4) | 0.4511 (3) | 0.1531 (2) | 0.0535 (16)* | 0.453 (10) |
O2B | 0.5977 (3) | 0.4568 (2) | 0.1741 (2) | 0.0599 (14)* | 0.547 (10) |
N1 | −0.03100 (18) | 0.16509 (12) | 0.22640 (6) | 0.0365 (4) | |
H1A | −0.1083 | 0.1414 | 0.2198 | 0.044* | |
N2 | 0.15676 (18) | 0.19979 (12) | 0.26803 (6) | 0.0375 (4) | |
N3 | −0.2246 (3) | −0.02281 (18) | 0.48686 (10) | 0.0870 (9) | |
C1 | 0.0502 (2) | 0.12506 (16) | 0.36298 (8) | 0.0426 (6) | |
H1 | 0.1312 | 0.1561 | 0.3647 | 0.051* | |
C2 | −0.0146 (2) | 0.11409 (14) | 0.31590 (7) | 0.0342 (5) | |
C3 | 0.0395 (2) | 0.15785 (14) | 0.27065 (8) | 0.0344 (5) | |
C4 | 0.1590 (2) | 0.23811 (14) | 0.22041 (8) | 0.0357 (5) | |
C5 | 0.0422 (2) | 0.21675 (14) | 0.19388 (8) | 0.0343 (5) | |
C6 | −0.1337 (2) | 0.06622 (15) | 0.31409 (9) | 0.0434 (6) | |
H6 | −0.1770 | 0.0572 | 0.2829 | 0.052* | |
C7 | −0.1890 (3) | 0.03175 (16) | 0.35818 (9) | 0.0477 (6) | |
H7 | −0.2695 | 0.0003 | 0.3565 | 0.057* | |
C8 | −0.1246 (3) | 0.04394 (15) | 0.40491 (8) | 0.0436 (6) | |
C9 | −0.0042 (3) | 0.09058 (16) | 0.40698 (9) | 0.0467 (6) | |
H9 | 0.0398 | 0.0986 | 0.4381 | 0.056* | |
C10 | −0.1822 (3) | 0.00799 (18) | 0.45080 (10) | 0.0578 (7) | |
C11 | 0.2726 (2) | 0.29387 (15) | 0.20442 (8) | 0.0386 (5) | |
C12 | 0.3309 (3) | 0.35160 (17) | 0.23854 (10) | 0.0514 (6) | |
H12 | 0.2973 | 0.3551 | 0.2718 | 0.062* | |
C13 | 0.4376 (3) | 0.40379 (18) | 0.22395 (12) | 0.0629 (8) | |
H13 | 0.4748 | 0.4419 | 0.2476 | 0.076* | |
C14 | 0.4902 (2) | 0.40073 (16) | 0.17515 (13) | 0.0615 (8) | |
C15 | 0.4324 (3) | 0.34407 (18) | 0.14061 (11) | 0.0585 (8) | |
H15 | 0.4656 | 0.3414 | 0.1073 | 0.070* | |
C16 | 0.3252 (2) | 0.29106 (16) | 0.15525 (10) | 0.0456 (6) | |
H16 | 0.2880 | 0.2530 | 0.1316 | 0.055* | |
C17 | −0.0113 (2) | 0.23867 (14) | 0.14317 (8) | 0.0353 (5) | |
C18 | −0.0015 (2) | 0.32100 (15) | 0.12327 (8) | 0.0412 (5) | |
H18 | 0.0428 | 0.3636 | 0.1419 | 0.049* | |
C19 | −0.0565 (2) | 0.34054 (16) | 0.07613 (9) | 0.0452 (6) | |
H19 | −0.0481 | 0.3959 | 0.0631 | 0.054* | |
C20 | −0.1239 (2) | 0.27831 (17) | 0.04820 (8) | 0.0441 (6) | |
C21 | −0.1337 (3) | 0.19588 (17) | 0.06687 (8) | 0.0482 (6) | |
H21 | −0.1776 | 0.1534 | 0.0480 | 0.058* | |
C22 | −0.0774 (2) | 0.17702 (16) | 0.11402 (8) | 0.0435 (6) | |
H22 | −0.0840 | 0.1212 | 0.1266 | 0.052* | |
C23 | −0.2822 (4) | 0.2570 (2) | −0.01908 (11) | 0.0846 (11) | |
H23A | −0.3084 | 0.2821 | −0.0511 | 0.127* | |
H23B | −0.3587 | 0.2573 | 0.0038 | 0.127* | |
H23C | −0.2527 | 0.1988 | −0.0246 | 0.127* | |
C24A | 0.6389 (7) | 0.4476 (4) | 0.1032 (2) | 0.060 (2)* | 0.453 (10) |
H24A | 0.7100 | 0.4896 | 0.0993 | 0.090* | 0.453 (10) |
H24B | 0.5667 | 0.4596 | 0.0795 | 0.090* | 0.453 (10) |
H24C | 0.6750 | 0.3913 | 0.0967 | 0.090* | 0.453 (10) |
C24B | 0.6769 (6) | 0.4419 (4) | 0.1306 (3) | 0.078 (2)* | 0.547 (10) |
H24D | 0.7534 | 0.4805 | 0.1305 | 0.117* | 0.547 (10) |
H24E | 0.6227 | 0.4514 | 0.1006 | 0.117* | 0.547 (10) |
H24F | 0.7091 | 0.3836 | 0.1309 | 0.117* | 0.547 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0731 (13) | 0.0811 (14) | 0.0465 (10) | −0.0207 (11) | −0.0216 (9) | 0.0206 (10) |
N1 | 0.0314 (9) | 0.0441 (11) | 0.0341 (10) | −0.0072 (8) | −0.0013 (7) | −0.0002 (8) |
N2 | 0.0312 (10) | 0.0452 (11) | 0.0362 (10) | −0.0021 (9) | −0.0015 (8) | 0.0025 (8) |
N3 | 0.123 (3) | 0.0772 (19) | 0.0605 (16) | −0.0118 (17) | 0.0285 (16) | 0.0173 (14) |
C1 | 0.0370 (12) | 0.0502 (14) | 0.0406 (12) | −0.0026 (11) | −0.0040 (10) | 0.0034 (11) |
C2 | 0.0306 (11) | 0.0363 (12) | 0.0357 (11) | 0.0029 (10) | 0.0005 (9) | 0.0023 (9) |
C3 | 0.0312 (11) | 0.0390 (12) | 0.0330 (11) | 0.0004 (10) | −0.0004 (9) | −0.0003 (9) |
C4 | 0.0319 (11) | 0.0400 (13) | 0.0350 (11) | −0.0009 (10) | 0.0026 (9) | −0.0004 (9) |
C5 | 0.0313 (11) | 0.0388 (12) | 0.0330 (11) | −0.0023 (10) | 0.0031 (9) | −0.0008 (9) |
C6 | 0.0443 (14) | 0.0446 (14) | 0.0412 (13) | −0.0043 (11) | −0.0032 (10) | 0.0023 (10) |
C7 | 0.0472 (14) | 0.0429 (14) | 0.0531 (15) | −0.0111 (12) | 0.0033 (11) | 0.0063 (11) |
C8 | 0.0549 (15) | 0.0368 (13) | 0.0393 (12) | 0.0024 (12) | 0.0084 (11) | 0.0053 (10) |
C9 | 0.0529 (15) | 0.0514 (15) | 0.0358 (12) | 0.0000 (13) | −0.0041 (11) | 0.0038 (11) |
C10 | 0.0739 (19) | 0.0497 (16) | 0.0499 (15) | −0.0016 (15) | 0.0118 (13) | 0.0092 (13) |
C11 | 0.0295 (11) | 0.0409 (13) | 0.0455 (13) | 0.0006 (10) | −0.0027 (9) | 0.0063 (10) |
C12 | 0.0471 (14) | 0.0529 (16) | 0.0543 (15) | −0.0068 (13) | −0.0078 (12) | 0.0037 (12) |
C13 | 0.0485 (16) | 0.0516 (17) | 0.089 (2) | −0.0145 (14) | −0.0167 (15) | 0.0069 (15) |
C14 | 0.0297 (13) | 0.0402 (15) | 0.115 (3) | −0.0059 (12) | 0.0046 (15) | 0.0234 (16) |
C15 | 0.0431 (14) | 0.0549 (17) | 0.0774 (19) | 0.0078 (14) | 0.0225 (13) | 0.0215 (14) |
C16 | 0.0369 (13) | 0.0468 (14) | 0.0531 (14) | 0.0026 (11) | 0.0057 (11) | 0.0059 (11) |
C17 | 0.0312 (11) | 0.0434 (13) | 0.0313 (11) | −0.0017 (10) | 0.0018 (9) | −0.0004 (9) |
C18 | 0.0389 (12) | 0.0427 (13) | 0.0419 (12) | −0.0048 (11) | −0.0024 (10) | −0.0030 (10) |
C19 | 0.0457 (13) | 0.0436 (14) | 0.0462 (13) | −0.0021 (12) | −0.0017 (11) | 0.0087 (11) |
C20 | 0.0416 (13) | 0.0569 (16) | 0.0337 (12) | −0.0058 (12) | −0.0014 (10) | 0.0070 (10) |
C21 | 0.0547 (15) | 0.0542 (16) | 0.0357 (12) | −0.0168 (13) | −0.0063 (11) | −0.0017 (11) |
C22 | 0.0502 (14) | 0.0429 (14) | 0.0375 (12) | −0.0103 (12) | −0.0003 (10) | 0.0046 (10) |
C23 | 0.091 (2) | 0.106 (3) | 0.0569 (18) | −0.024 (2) | −0.0336 (17) | 0.0160 (18) |
O1—C20 | 1.367 (3) | C11—C12 | 1.388 (3) |
O1—C23 | 1.395 (3) | C12—C13 | 1.378 (4) |
O2A—C14 | 1.3663 (10) | C12—H12 | 0.9300 |
O2A—C24A | 1.3961 (11) | C13—C14 | 1.377 (4) |
O2B—C14 | 1.3677 (10) | C13—H13 | 0.9300 |
O2B—C24B | 1.3966 (11) | C14—C15 | 1.383 (4) |
N1—C3 | 1.352 (2) | C15—C16 | 1.390 (3) |
N1—C5 | 1.372 (3) | C15—H15 | 0.9300 |
N1—H1A | 0.8600 | C16—H16 | 0.9300 |
N2—C3 | 1.323 (3) | C17—C22 | 1.385 (3) |
N2—C4 | 1.380 (3) | C17—C18 | 1.385 (3) |
N3—C10 | 1.136 (3) | C18—C19 | 1.379 (3) |
C1—C9 | 1.377 (3) | C18—H18 | 0.9300 |
C1—C2 | 1.395 (3) | C19—C20 | 1.381 (3) |
C1—H1 | 0.9300 | C19—H19 | 0.9300 |
C2—C6 | 1.386 (3) | C20—C21 | 1.375 (3) |
C2—C3 | 1.464 (3) | C21—C22 | 1.382 (3) |
C4—C5 | 1.380 (3) | C21—H21 | 0.9300 |
C4—C11 | 1.472 (3) | C22—H22 | 0.9300 |
C5—C17 | 1.466 (3) | C23—H23A | 0.9600 |
C6—C7 | 1.381 (3) | C23—H23B | 0.9600 |
C6—H6 | 0.9300 | C23—H23C | 0.9600 |
C7—C8 | 1.388 (3) | C24A—H24A | 0.9600 |
C7—H7 | 0.9300 | C24A—H24B | 0.9600 |
C8—C9 | 1.386 (3) | C24A—H24C | 0.9600 |
C8—C10 | 1.439 (3) | C24B—H24D | 0.9600 |
C9—H9 | 0.9300 | C24B—H24E | 0.9600 |
C11—C16 | 1.386 (3) | C24B—H24F | 0.9600 |
C20—O1—C23 | 118.1 (2) | O2A—C14—C15 | 112.1 (4) |
C14—O2A—C24A | 128.5 (5) | O2B—C14—C15 | 135.2 (3) |
C14—O2B—C24B | 109.7 (4) | C13—C14—C15 | 118.3 (2) |
C3—N1—C5 | 108.16 (17) | C14—C15—C16 | 120.5 (2) |
C3—N1—H1A | 125.9 | C14—C15—H15 | 119.7 |
C5—N1—H1A | 125.9 | C16—C15—H15 | 119.7 |
C3—N2—C4 | 105.87 (17) | C11—C16—C15 | 121.2 (3) |
C9—C1—C2 | 120.9 (2) | C11—C16—H16 | 119.4 |
C9—C1—H1 | 119.6 | C15—C16—H16 | 119.4 |
C2—C1—H1 | 119.6 | C22—C17—C18 | 117.7 (2) |
C6—C2—C1 | 118.6 (2) | C22—C17—C5 | 120.3 (2) |
C6—C2—C3 | 121.81 (19) | C18—C17—C5 | 122.0 (2) |
C1—C2—C3 | 119.4 (2) | C19—C18—C17 | 120.8 (2) |
N2—C3—N1 | 111.01 (18) | C19—C18—H18 | 119.6 |
N2—C3—C2 | 125.83 (18) | C17—C18—H18 | 119.6 |
N1—C3—C2 | 123.02 (19) | C18—C19—C20 | 120.4 (2) |
C5—C4—N2 | 109.63 (18) | C18—C19—H19 | 119.8 |
C5—C4—C11 | 128.84 (19) | C20—C19—H19 | 119.8 |
N2—C4—C11 | 121.52 (18) | O1—C20—C21 | 124.3 (2) |
N1—C5—C4 | 105.28 (18) | O1—C20—C19 | 115.8 (2) |
N1—C5—C17 | 120.63 (18) | C21—C20—C19 | 119.9 (2) |
C4—C5—C17 | 134.1 (2) | C20—C21—C22 | 119.1 (2) |
C7—C6—C2 | 120.7 (2) | C20—C21—H21 | 120.4 |
C7—C6—H6 | 119.7 | C22—C21—H21 | 120.4 |
C2—C6—H6 | 119.7 | C21—C22—C17 | 122.0 (2) |
C6—C7—C8 | 120.2 (2) | C21—C22—H22 | 119.0 |
C6—C7—H7 | 119.9 | C17—C22—H22 | 119.0 |
C8—C7—H7 | 119.9 | O1—C23—H23A | 109.5 |
C9—C8—C7 | 119.5 (2) | O1—C23—H23B | 109.5 |
C9—C8—C10 | 120.3 (2) | H23A—C23—H23B | 109.5 |
C7—C8—C10 | 120.1 (2) | O1—C23—H23C | 109.5 |
C1—C9—C8 | 120.1 (2) | H23A—C23—H23C | 109.5 |
C1—C9—H9 | 120.0 | H23B—C23—H23C | 109.5 |
C8—C9—H9 | 120.0 | O2A—C24A—H24A | 109.5 |
N3—C10—C8 | 177.5 (3) | O2A—C24A—H24B | 109.5 |
C16—C11—C12 | 117.6 (2) | H24A—C24A—H24B | 109.5 |
C16—C11—C4 | 121.8 (2) | O2A—C24A—H24C | 109.5 |
C12—C11—C4 | 120.6 (2) | H24A—C24A—H24C | 109.5 |
C13—C12—C11 | 121.0 (3) | H24B—C24A—H24C | 109.5 |
C13—C12—H12 | 119.5 | O2B—C24B—H24D | 109.5 |
C11—C12—H12 | 119.5 | O2B—C24B—H24E | 109.5 |
C14—C13—C12 | 121.4 (3) | H24D—C24B—H24E | 109.5 |
C14—C13—H13 | 119.3 | O2B—C24B—H24F | 109.5 |
C12—C13—H13 | 119.3 | H24D—C24B—H24F | 109.5 |
O2A—C14—C13 | 129.4 (4) | H24E—C24B—H24F | 109.5 |
O2B—C14—C13 | 106.5 (3) | ||
C9—C1—C2—C6 | −1.3 (3) | C11—C12—C13—C14 | 0.0 (4) |
C9—C1—C2—C3 | 174.7 (2) | C24A—O2A—C14—O2B | 162.0 (10) |
C4—N2—C3—N1 | 2.1 (2) | C24A—O2A—C14—C13 | −179.1 (5) |
C4—N2—C3—C2 | −173.7 (2) | C24A—O2A—C14—C15 | −4.3 (6) |
C5—N1—C3—N2 | −2.0 (2) | C24B—O2B—C14—O2A | −29.9 (6) |
C5—N1—C3—C2 | 173.91 (19) | C24B—O2B—C14—C13 | 165.2 (4) |
C6—C2—C3—N2 | −175.1 (2) | C24B—O2B—C14—C15 | −11.9 (6) |
C1—C2—C3—N2 | 9.1 (3) | C12—C13—C14—O2A | 175.0 (3) |
C6—C2—C3—N1 | 9.6 (3) | C12—C13—C14—O2B | −177.2 (3) |
C1—C2—C3—N1 | −166.2 (2) | C12—C13—C14—C15 | 0.5 (4) |
C3—N2—C4—C5 | −1.4 (2) | O2A—C14—C15—C16 | −176.2 (3) |
C3—N2—C4—C11 | 177.4 (2) | O2B—C14—C15—C16 | 176.1 (3) |
C3—N1—C5—C4 | 1.1 (2) | C13—C14—C15—C16 | −0.8 (4) |
C3—N1—C5—C17 | −178.0 (2) | C12—C11—C16—C15 | 0.1 (3) |
N2—C4—C5—N1 | 0.2 (2) | C4—C11—C16—C15 | 180.0 (2) |
C11—C4—C5—N1 | −178.5 (2) | C14—C15—C16—C11 | 0.5 (4) |
N2—C4—C5—C17 | 179.1 (2) | N1—C5—C17—C22 | −40.5 (3) |
C11—C4—C5—C17 | 0.4 (4) | C4—C5—C17—C22 | 140.8 (3) |
C1—C2—C6—C7 | 1.5 (3) | N1—C5—C17—C18 | 137.8 (2) |
C3—C2—C6—C7 | −174.4 (2) | C4—C5—C17—C18 | −41.0 (4) |
C2—C6—C7—C8 | −0.7 (4) | C22—C17—C18—C19 | 0.4 (3) |
C6—C7—C8—C9 | −0.3 (4) | C5—C17—C18—C19 | −178.0 (2) |
C6—C7—C8—C10 | −180.0 (2) | C17—C18—C19—C20 | 0.8 (4) |
C2—C1—C9—C8 | 0.3 (4) | C23—O1—C20—C21 | 23.1 (4) |
C7—C8—C9—C1 | 0.5 (4) | C23—O1—C20—C19 | −157.8 (3) |
C10—C8—C9—C1 | −179.8 (2) | C18—C19—C20—O1 | 179.4 (2) |
C5—C4—C11—C16 | −41.6 (3) | C18—C19—C20—C21 | −1.5 (4) |
N2—C4—C11—C16 | 139.9 (2) | O1—C20—C21—C22 | −179.9 (2) |
C5—C4—C11—C12 | 138.3 (2) | C19—C20—C21—C22 | 1.1 (4) |
N2—C4—C11—C12 | −40.2 (3) | C20—C21—C22—C17 | 0.1 (4) |
C16—C11—C12—C13 | −0.3 (4) | C18—C17—C22—C21 | −0.8 (3) |
C4—C11—C12—C13 | 179.7 (2) | C5—C17—C22—C21 | 177.6 (2) |