Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000438/is2133sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000438/is2133Isup2.hkl |
CCDC reference: 636709
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C22H26N2O4 | Z = 2 |
Mr = 382.45 | F(000) = 408 |
Triclinic, P1 | Dx = 1.234 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.090 (5) Å | Cell parameters from 4027 reflections |
b = 10.970 (5) Å | θ = 2.2–30.5° |
c = 11.678 (5) Å | µ = 0.09 mm−1 |
α = 115.254 (5)° | T = 294 K |
β = 112.401 (5)° | Needle, pale yellow |
γ = 95.258 (5)° | 0.2 × 0.2 × 0.2 mm |
V = 1029.7 (8) Å3 |
Rigaku R-AXIS RAPID-S diffractometer | 4115 reflections with I > 2σ(I) |
ω scans | Rint = 0.048 |
Absorption correction: multi-scan (Blessing, 1995) | θmax = 30.5°, θmin = 2.2° |
Tmin = 0.973, Tmax = 0.983 | h = −14→14 |
30731 measured reflections | k = −13→15 |
6285 independent reflections | l = −16→16 |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0753P)2 + 0.1247P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.061 | (Δ/σ)max < 0.001 |
wR(F2) = 0.179 | Δρmax = 0.22 e Å−3 |
S = 1.05 | Δρmin = −0.20 e Å−3 |
6285 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
262 parameters | Extinction coefficient: 0.039 (5) |
0 restraints |
Experimental. Uv-vis (λmax, nm; in EtOH): 422, 327, 295, 280. |
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 | ||
O3 | 0.70921 (14) | 0.51904 (13) | −0.00418 (13) | 0.0671 (3) | |
H21 | 0.7306 | 0.5619 | 0.0808 | 0.101* | |
O1 | 0.73336 (12) | 0.24167 (12) | 0.34255 (13) | 0.0656 (3) | |
H7 | 0.7549 | 0.3265 | 0.3698 | 0.098* | |
O4 | 0.66880 (17) | 0.36611 (17) | −0.26575 (14) | 0.0843 (4) | |
O2 | 0.62739 (15) | −0.03197 (13) | 0.23482 (16) | 0.0780 (4) | |
C22 | 0.6475 (3) | 0.2882 (4) | −0.4068 (2) | 0.1339 (13) | |
H22A | 0.5718 | 0.3105 | −0.468 | 0.201* | |
H22B | 0.6159 | 0.1889 | −0.4398 | 0.201* | |
H22C | 0.7404 | 0.3122 | −0.4086 | 0.201* | |
H15 | 0.992 (2) | 0.4822 (19) | 0.305 (2) | 0.069 (5)* | |
H8 | 0.479 (2) | 0.4559 (19) | 0.2324 (19) | 0.068 (5)* | |
N2 | 0.85450 (15) | 0.59426 (13) | 0.26929 (13) | 0.0531 (3) | |
C16 | 0.89708 (17) | 0.41847 (15) | 0.08687 (16) | 0.0495 (3) | |
N1 | 0.68645 (15) | 0.47760 (14) | 0.36649 (14) | 0.0546 (3) | |
C15 | 0.92030 (18) | 0.50197 (16) | 0.23275 (16) | 0.0527 (4) | |
C8 | 0.55124 (19) | 0.40773 (17) | 0.26931 (17) | 0.0543 (4) | |
C9 | 0.73833 (18) | 0.63031 (16) | 0.42458 (16) | 0.0532 (4) | |
H9 | 0.6616 | 0.6581 | 0.3674 | 0.064* | |
C21 | 0.79314 (17) | 0.43035 (16) | −0.02469 (16) | 0.0508 (3) | |
C7 | 0.58586 (17) | 0.17926 (17) | 0.24817 (16) | 0.0523 (3) | |
C6 | 0.49247 (17) | 0.25594 (17) | 0.20876 (16) | 0.0532 (4) | |
C17 | 0.97957 (19) | 0.32407 (17) | 0.05808 (17) | 0.0585 (4) | |
H17 | 1.049 | 0.3158 | 0.1322 | 0.07* | |
C20 | 0.77277 (18) | 0.34678 (18) | −0.16410 (17) | 0.0573 (4) | |
C14 | 0.88448 (17) | 0.66764 (16) | 0.41848 (15) | 0.0524 (4) | |
H14 | 0.9582 | 0.6343 | 0.4713 | 0.063* | |
C19 | 0.85570 (19) | 0.25441 (18) | −0.18895 (17) | 0.0605 (4) | |
H19 | 0.8418 | 0.1987 | −0.2814 | 0.073* | |
C2 | 0.52632 (19) | 0.03261 (18) | 0.18849 (18) | 0.0582 (4) | |
C18 | 0.95913 (19) | 0.24380 (17) | −0.07802 (18) | 0.0625 (4) | |
H18 | 1.0151 | 0.1818 | −0.0959 | 0.075* | |
C13 | 0.9491 (2) | 0.82687 (17) | 0.48640 (18) | 0.0615 (4) | |
H13A | 1.0443 | 0.8475 | 0.4858 | 0.074* | |
H13B | 0.8808 | 0.8598 | 0.4301 | 0.074* | |
C5 | 0.34032 (19) | 0.1848 (2) | 0.1090 (2) | 0.0673 (4) | |
H5 | 0.2775 | 0.2349 | 0.0817 | 0.081* | |
C10 | 0.7667 (2) | 0.70859 (19) | 0.57942 (18) | 0.0667 (5) | |
H10A | 0.6731 | 0.6872 | 0.5826 | 0.08* | |
H10B | 0.8374 | 0.6761 | 0.6344 | 0.08* | |
C3 | 0.3760 (2) | −0.0339 (2) | 0.0916 (2) | 0.0677 (5) | |
H3 | 0.336 | −0.1306 | 0.0527 | 0.081* | |
C12 | 0.9732 (2) | 0.90522 (19) | 0.6389 (2) | 0.0724 (5) | |
H12A | 1.0072 | 1.0063 | 0.6764 | 0.087* | |
H12B | 1.0508 | 0.8811 | 0.698 | 0.087* | |
C4 | 0.2836 (2) | 0.0422 (2) | 0.0515 (2) | 0.0743 (5) | |
H4 | 0.1825 | −0.004 | −0.0148 | 0.089* | |
C11 | 0.8294 (2) | 0.86791 (19) | 0.6464 (2) | 0.0768 (5) | |
H11A | 0.7552 | 0.9017 | 0.5963 | 0.092* | |
H11B | 0.8495 | 0.9145 | 0.7456 | 0.092* | |
C1 | 0.5769 (3) | −0.1810 (2) | 0.1712 (3) | 0.0873 (6) | |
H1A | 0.6581 | −0.2128 | 0.2127 | 0.131* | |
H1B | 0.5431 | −0.2242 | 0.0701 | 0.131* | |
H1C | 0.4953 | −0.2069 | 0.1878 | 0.131* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.0795 (8) | 0.0780 (8) | 0.0600 (7) | 0.0479 (7) | 0.0396 (6) | 0.0367 (6) |
O1 | 0.0523 (6) | 0.0581 (7) | 0.0711 (8) | 0.0142 (5) | 0.0155 (5) | 0.0320 (6) |
O4 | 0.0899 (9) | 0.1212 (12) | 0.0564 (7) | 0.0568 (9) | 0.0385 (7) | 0.0477 (8) |
O2 | 0.0715 (8) | 0.0585 (7) | 0.0929 (10) | 0.0188 (6) | 0.0243 (7) | 0.0415 (7) |
C22 | 0.126 (2) | 0.229 (4) | 0.0592 (12) | 0.101 (2) | 0.0506 (14) | 0.0671 (18) |
N2 | 0.0621 (8) | 0.0484 (7) | 0.0480 (7) | 0.0208 (6) | 0.0287 (6) | 0.0202 (5) |
C16 | 0.0528 (8) | 0.0432 (7) | 0.0480 (7) | 0.0161 (6) | 0.0241 (6) | 0.0184 (6) |
N1 | 0.0587 (8) | 0.0521 (7) | 0.0535 (7) | 0.0194 (6) | 0.0260 (6) | 0.0264 (6) |
C15 | 0.0561 (8) | 0.0485 (8) | 0.0470 (8) | 0.0190 (7) | 0.0222 (6) | 0.0195 (6) |
C8 | 0.0583 (9) | 0.0580 (9) | 0.0512 (8) | 0.0240 (7) | 0.0280 (7) | 0.0277 (7) |
C9 | 0.0601 (9) | 0.0487 (8) | 0.0515 (8) | 0.0221 (7) | 0.0268 (7) | 0.0238 (6) |
C21 | 0.0535 (8) | 0.0491 (8) | 0.0538 (8) | 0.0210 (6) | 0.0295 (7) | 0.0242 (6) |
C7 | 0.0493 (8) | 0.0566 (9) | 0.0492 (8) | 0.0147 (7) | 0.0227 (6) | 0.0257 (7) |
C6 | 0.0520 (8) | 0.0586 (9) | 0.0480 (8) | 0.0174 (7) | 0.0239 (6) | 0.0253 (7) |
C17 | 0.0629 (9) | 0.0516 (8) | 0.0535 (8) | 0.0259 (7) | 0.0253 (7) | 0.0202 (7) |
C20 | 0.0567 (9) | 0.0647 (9) | 0.0501 (8) | 0.0210 (7) | 0.0263 (7) | 0.0269 (7) |
C14 | 0.0598 (9) | 0.0506 (8) | 0.0440 (7) | 0.0222 (7) | 0.0256 (7) | 0.0193 (6) |
C19 | 0.0633 (9) | 0.0572 (9) | 0.0498 (8) | 0.0178 (7) | 0.0299 (7) | 0.0147 (7) |
C2 | 0.0596 (9) | 0.0580 (9) | 0.0568 (9) | 0.0161 (7) | 0.0267 (7) | 0.0294 (7) |
C18 | 0.0639 (10) | 0.0542 (9) | 0.0616 (10) | 0.0271 (8) | 0.0321 (8) | 0.0185 (7) |
C13 | 0.0688 (10) | 0.0504 (8) | 0.0578 (9) | 0.0166 (7) | 0.0325 (8) | 0.0188 (7) |
C5 | 0.0536 (9) | 0.0743 (11) | 0.0659 (10) | 0.0196 (8) | 0.0210 (8) | 0.0347 (9) |
C10 | 0.0823 (12) | 0.0654 (10) | 0.0581 (10) | 0.0267 (9) | 0.0418 (9) | 0.0269 (8) |
C3 | 0.0638 (10) | 0.0611 (10) | 0.0661 (10) | 0.0070 (8) | 0.0260 (8) | 0.0284 (8) |
C12 | 0.0836 (12) | 0.0547 (9) | 0.0584 (10) | 0.0161 (9) | 0.0353 (9) | 0.0110 (8) |
C4 | 0.0523 (9) | 0.0783 (13) | 0.0697 (11) | 0.0073 (9) | 0.0170 (8) | 0.0314 (10) |
C11 | 0.0955 (14) | 0.0616 (10) | 0.0674 (11) | 0.0264 (10) | 0.0501 (11) | 0.0165 (9) |
C1 | 0.0977 (16) | 0.0608 (11) | 0.0981 (16) | 0.0232 (11) | 0.0379 (13) | 0.0424 (11) |
O3—C21 | 1.3521 (18) | C17—C18 | 1.366 (2) |
O3—H21 | 0.82 | C17—H17 | 0.93 |
O1—C7 | 1.3482 (19) | C20—C19 | 1.379 (2) |
O1—H7 | 0.82 | C14—C13 | 1.523 (2) |
O4—C20 | 1.364 (2) | C14—H14 | 0.98 |
O4—C22 | 1.409 (3) | C19—C18 | 1.379 (2) |
O2—C2 | 1.369 (2) | C19—H19 | 0.93 |
O2—C1 | 1.416 (2) | C2—C3 | 1.378 (2) |
C22—H22A | 0.96 | C18—H18 | 0.93 |
C22—H22B | 0.96 | C13—C12 | 1.515 (2) |
C22—H22C | 0.96 | C13—H13A | 0.97 |
N2—C15 | 1.2721 (19) | C13—H13B | 0.97 |
N2—C14 | 1.4601 (19) | C5—C4 | 1.368 (3) |
C16—C21 | 1.394 (2) | C5—H5 | 0.93 |
C16—C17 | 1.397 (2) | C10—C11 | 1.523 (3) |
C16—C15 | 1.456 (2) | C10—H10A | 0.97 |
N1—C8 | 1.274 (2) | C10—H10B | 0.97 |
N1—C9 | 1.463 (2) | C3—C4 | 1.389 (3) |
C15—H15 | 1.006 (19) | C3—H3 | 0.93 |
C8—C6 | 1.456 (2) | C12—C11 | 1.516 (3) |
C8—H8 | 1.012 (19) | C12—H12A | 0.97 |
C9—C10 | 1.525 (2) | C12—H12B | 0.97 |
C9—C14 | 1.530 (2) | C4—H4 | 0.93 |
C9—H9 | 0.98 | C11—H11A | 0.97 |
C21—C20 | 1.404 (2) | C11—H11B | 0.97 |
C7—C6 | 1.397 (2) | C1—H1A | 0.96 |
C7—C2 | 1.408 (2) | C1—H1B | 0.96 |
C6—C5 | 1.402 (2) | C1—H1C | 0.96 |
C21—O3—H21 | 109.5 | C20—C19—C18 | 120.65 (15) |
C7—O1—H7 | 109.5 | C20—C19—H19 | 119.7 |
C20—O4—C22 | 117.29 (17) | C18—C19—H19 | 119.7 |
C2—O2—C1 | 117.76 (15) | O2—C2—C3 | 125.44 (16) |
O4—C22—H22A | 109.5 | O2—C2—C7 | 115.08 (14) |
O4—C22—H22B | 109.5 | C3—C2—C7 | 119.48 (16) |
H22A—C22—H22B | 109.5 | C17—C18—C19 | 120.22 (15) |
O4—C22—H22C | 109.5 | C17—C18—H18 | 119.9 |
H22A—C22—H22C | 109.5 | C19—C18—H18 | 119.9 |
H22B—C22—H22C | 109.5 | C12—C13—C14 | 111.56 (14) |
C15—N2—C14 | 117.97 (13) | C12—C13—H13A | 109.3 |
C21—C16—C17 | 119.45 (14) | C14—C13—H13A | 109.3 |
C21—C16—C15 | 121.11 (13) | C12—C13—H13B | 109.3 |
C17—C16—C15 | 119.44 (14) | C14—C13—H13B | 109.3 |
C8—N1—C9 | 119.23 (13) | H13A—C13—H13B | 108 |
N2—C15—C16 | 123.52 (14) | C4—C5—C6 | 120.49 (17) |
N2—C15—H15 | 120.7 (11) | C4—C5—H5 | 119.8 |
C16—C15—H15 | 115.8 (11) | C6—C5—H5 | 119.8 |
N1—C8—C6 | 121.77 (15) | C11—C10—C9 | 111.31 (14) |
N1—C8—H8 | 121.4 (10) | C11—C10—H10A | 109.4 |
C6—C8—H8 | 116.8 (10) | C9—C10—H10A | 109.4 |
N1—C9—C10 | 109.77 (13) | C11—C10—H10B | 109.4 |
N1—C9—C14 | 109.01 (12) | C9—C10—H10B | 109.4 |
C10—C9—C14 | 109.55 (13) | H10A—C10—H10B | 108 |
N1—C9—H9 | 109.5 | C2—C3—C4 | 120.54 (17) |
C10—C9—H9 | 109.5 | C2—C3—H3 | 119.7 |
C14—C9—H9 | 109.5 | C4—C3—H3 | 119.7 |
O3—C21—C16 | 122.38 (13) | C13—C12—C11 | 111.19 (15) |
O3—C21—C20 | 118.24 (14) | C13—C12—H12A | 109.4 |
C16—C21—C20 | 119.38 (14) | C11—C12—H12A | 109.4 |
O1—C7—C6 | 121.83 (14) | C13—C12—H12B | 109.4 |
O1—C7—C2 | 118.27 (14) | C11—C12—H12B | 109.4 |
C6—C7—C2 | 119.90 (15) | H12A—C12—H12B | 108 |
C7—C6—C5 | 119.17 (16) | C5—C4—C3 | 120.42 (17) |
C7—C6—C8 | 120.94 (14) | C5—C4—H4 | 119.8 |
C5—C6—C8 | 119.90 (15) | C3—C4—H4 | 119.8 |
C18—C17—C16 | 120.58 (15) | C12—C11—C10 | 110.97 (15) |
C18—C17—H17 | 119.7 | C12—C11—H11A | 109.4 |
C16—C17—H17 | 119.7 | C10—C11—H11A | 109.4 |
O4—C20—C19 | 125.28 (15) | C12—C11—H11B | 109.4 |
O4—C20—C21 | 114.99 (14) | C10—C11—H11B | 109.4 |
C19—C20—C21 | 119.73 (15) | H11A—C11—H11B | 108 |
N2—C14—C13 | 110.91 (13) | O2—C1—H1A | 109.5 |
N2—C14—C9 | 108.78 (12) | O2—C1—H1B | 109.5 |
C13—C14—C9 | 111.29 (12) | H1A—C1—H1B | 109.5 |
N2—C14—H14 | 108.6 | O2—C1—H1C | 109.5 |
C13—C14—H14 | 108.6 | H1A—C1—H1C | 109.5 |
C9—C14—H14 | 108.6 | H1B—C1—H1C | 109.5 |
C14—N2—C15—C16 | 178.21 (13) | C10—C9—C14—N2 | −178.77 (12) |
C21—C16—C15—N2 | −3.4 (2) | N1—C9—C14—C13 | −176.41 (13) |
C17—C16—C15—N2 | 177.10 (16) | C10—C9—C14—C13 | −56.29 (17) |
C9—N1—C8—C6 | −179.13 (13) | O4—C20—C19—C18 | 179.47 (17) |
C8—N1—C9—C10 | 111.36 (17) | C21—C20—C19—C18 | −0.3 (3) |
C8—N1—C9—C14 | −128.65 (15) | C1—O2—C2—C3 | 4.7 (3) |
C17—C16—C21—O3 | 179.63 (15) | C1—O2—C2—C7 | −175.62 (16) |
C15—C16—C21—O3 | 0.1 (2) | O1—C7—C2—O2 | 0.4 (2) |
C17—C16—C21—C20 | 0.3 (2) | C6—C7—C2—O2 | −179.78 (14) |
C15—C16—C21—C20 | −179.24 (14) | O1—C7—C2—C3 | −179.90 (15) |
O1—C7—C6—C5 | 179.38 (15) | C6—C7—C2—C3 | −0.1 (2) |
C2—C7—C6—C5 | −0.5 (2) | C16—C17—C18—C19 | −0.5 (3) |
O1—C7—C6—C8 | −0.4 (2) | C20—C19—C18—C17 | 0.6 (3) |
C2—C7—C6—C8 | 179.79 (14) | N2—C14—C13—C12 | 177.00 (14) |
N1—C8—C6—C7 | −4.5 (2) | C9—C14—C13—C12 | 55.75 (19) |
N1—C8—C6—C5 | 175.71 (15) | C7—C6—C5—C4 | 0.4 (3) |
C21—C16—C17—C18 | 0.0 (2) | C8—C6—C5—C4 | −179.86 (16) |
C15—C16—C17—C18 | 179.54 (15) | N1—C9—C10—C11 | 176.78 (15) |
C22—O4—C20—C19 | −1.9 (3) | C14—C9—C10—C11 | 57.12 (19) |
C22—O4—C20—C21 | 178.0 (2) | O2—C2—C3—C4 | −179.65 (18) |
O3—C21—C20—O4 | 0.7 (2) | C7—C2—C3—C4 | 0.7 (3) |
C16—C21—C20—O4 | −179.94 (14) | C14—C13—C12—C11 | −54.9 (2) |
O3—C21—C20—C19 | −179.50 (15) | C6—C5—C4—C3 | 0.2 (3) |
C16—C21—C20—C19 | −0.1 (2) | C2—C3—C4—C5 | −0.7 (3) |
C15—N2—C14—C13 | 121.25 (16) | C13—C12—C11—C10 | 55.4 (2) |
C15—N2—C14—C9 | −116.03 (16) | C9—C10—C11—C12 | −57.1 (2) |
N1—C9—C14—N2 | 61.10 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H7···N1 | 0.82 | 1.86 | 2.590 (3) | 147 |
O3—H21···N2 | 0.82 | 1.92 | 2.644 (2) | 147 |