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
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.061
- wR factor = 0.178
- Data-to-parameter ratio = 24.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 500 Ang. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 500 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.70 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.19 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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 |