Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801015197/ya6056sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801015197/ya6056Isup2.hkl |
CCDC reference: 175369
H atoms were placed in calculated positions with Uiso constrained to be 1.5Ueq of the carrier atom for the methyl-H and 1.2Ueq for the remaining H atoms.
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997), PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).
Fig. 1. View of the title compound showing the labelling of all non-H atoms. Displacement ellipsoids are shown at 50% probability level. H atoms are drawn as circles of arbitrary radii. |
C22H24N2O3 | Z = 2 |
Mr = 364.43 | F(000) = 388 |
Triclinic, P1 | Dx = 1.235 Mg m−3 |
a = 7.5983 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.4757 (4) Å | Cell parameters from 8836 reflections |
c = 11.5774 (4) Å | θ = 3.4–27.4° |
α = 84.8457 (15)° | µ = 0.08 mm−1 |
β = 82.2149 (16)° | T = 291 K |
γ = 79.0257 (17)° | Block, red |
V = 979.77 (6) Å3 | 0.25 × 0.23 × 0.23 mm |
Nonius KappaCCD diffractometer | 1655 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 27.4°, θmin = 3.4° |
Detector resolution: 10 vertical, 18 horizontal pixels mm-1 | h = −9→9 |
303 frames via ω–rotation (Δω=1°) with 3 sets at different κ–angles and two times 30 s per frame scans | k = −14→14 |
8836 measured reflections | l = −14→15 |
4334 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 0.90 | w = 1/[σ2(Fo2) + (0.0358P)2] where P = (Fo2 + 2Fc2)/3 |
4334 reflections | (Δ/σ)max < 0.001 |
249 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C22H24N2O3 | γ = 79.0257 (17)° |
Mr = 364.43 | V = 979.77 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.5983 (3) Å | Mo Kα radiation |
b = 11.4757 (4) Å | µ = 0.08 mm−1 |
c = 11.5774 (4) Å | T = 291 K |
α = 84.8457 (15)° | 0.25 × 0.23 × 0.23 mm |
β = 82.2149 (16)° |
Nonius KappaCCD diffractometer | 1655 reflections with I > 2σ(I) |
8836 measured reflections | Rint = 0.028 |
4334 independent reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 0.90 | Δρmax = 0.13 e Å−3 |
4334 reflections | Δρmin = −0.15 e Å−3 |
249 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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.74169 (19) | −0.08122 (12) | −0.28665 (12) | 0.0609 (4) | |
O2 | −0.8013 (2) | 0.24708 (15) | −0.55906 (14) | 0.0847 (6) | |
O3 | −0.3033 (2) | 0.16507 (13) | −0.32776 (13) | 0.0679 (5) | |
N1 | −0.2419 (3) | −0.54406 (19) | 0.3472 (2) | 0.0922 (8) | |
N2 | −0.6795 (3) | −0.49470 (17) | 0.13631 (18) | 0.0741 (6) | |
C1 | −0.3629 (3) | −0.17593 (16) | −0.04722 (17) | 0.0428 (5) | |
C2 | −0.4176 (3) | −0.27016 (16) | 0.01834 (17) | 0.0457 (6) | |
H2 | −0.5197 | −0.2954 | 0.0008 | 0.055* | |
C3 | −0.3285 (3) | −0.33195 (17) | 0.11146 (17) | 0.0422 (5) | |
C4 | −0.1674 (3) | −0.28993 (17) | 0.14223 (17) | 0.0477 (6) | |
H4A | −0.0859 | −0.3574 | 0.1734 | 0.057* | |
H4B | −0.2063 | −0.2344 | 0.2030 | 0.057* | |
C5 | −0.0651 (3) | −0.22925 (17) | 0.03806 (18) | 0.0447 (5) | |
C6 | −0.2004 (3) | −0.13312 (16) | −0.01925 (17) | 0.0484 (6) | |
H6A | −0.2400 | −0.0688 | 0.0326 | 0.058* | |
H6B | −0.1398 | −0.1011 | −0.0909 | 0.058* | |
C7 | −0.3895 (3) | −0.42658 (18) | 0.17406 (17) | 0.0465 (6) | |
C8 | −0.3043 (3) | −0.49138 (19) | 0.2702 (2) | 0.0583 (6) | |
C9 | −0.5491 (3) | −0.46511 (19) | 0.15193 (19) | 0.0541 (6) | |
C10 | 0.0280 (3) | −0.32090 (18) | −0.04900 (18) | 0.0594 (6) | |
H10A | 0.1012 | −0.2837 | −0.1102 | 0.089* | |
H10B | −0.0616 | −0.3518 | −0.0820 | 0.089* | |
H10C | 0.1029 | −0.3848 | −0.0095 | 0.089* | |
C11 | 0.0758 (3) | −0.17123 (19) | 0.0819 (2) | 0.0636 (7) | |
H11A | 0.1394 | −0.1321 | 0.0171 | 0.095* | |
H11B | 0.1598 | −0.2311 | 0.1194 | 0.095* | |
H11C | 0.0170 | −0.1140 | 0.1368 | 0.095* | |
C12 | −0.4641 (3) | −0.11889 (17) | −0.14026 (17) | 0.0492 (6) | |
H12 | −0.5619 | −0.1514 | −0.1541 | 0.059* | |
C13 | −0.4290 (3) | −0.02245 (17) | −0.20889 (17) | 0.0487 (6) | |
H13 | −0.3286 | 0.0065 | −0.1939 | 0.058* | |
C14 | −0.5230 (3) | 0.04287 (17) | −0.30199 (17) | 0.0440 (5) | |
C15 | −0.6795 (3) | 0.01705 (17) | −0.34007 (17) | 0.0475 (6) | |
C16 | −0.7677 (3) | 0.08601 (19) | −0.42457 (18) | 0.0573 (6) | |
H16 | −0.8717 | 0.0670 | −0.4464 | 0.069* | |
C17 | −0.7012 (3) | 0.1842 (2) | −0.47721 (18) | 0.0593 (6) | |
C18 | −0.5456 (3) | 0.21331 (18) | −0.44710 (18) | 0.0558 (6) | |
H18 | −0.5001 | 0.2787 | −0.4839 | 0.067* | |
C19 | −0.4591 (3) | 0.14241 (18) | −0.36065 (17) | 0.0491 (6) | |
C20 | −0.8898 (3) | −0.1165 (2) | −0.3313 (2) | 0.0723 (7) | |
H20A | −0.9971 | −0.0580 | −0.3153 | 0.109* | |
H20B | −0.9091 | −0.1920 | −0.2943 | 0.109* | |
H20C | −0.8623 | −0.1229 | −0.4142 | 0.109* | |
C21 | −0.7421 (4) | 0.3488 (2) | −0.6206 (2) | 0.1027 (10) | |
H21A | −0.7395 | 0.4066 | −0.5662 | 0.154* | |
H21B | −0.8238 | 0.3826 | −0.6762 | 0.154* | |
H21C | −0.6231 | 0.3254 | −0.6608 | 0.154* | |
C22 | −0.2380 (3) | 0.27014 (19) | −0.37544 (19) | 0.0646 (7) | |
H22A | −0.2101 | 0.2671 | −0.4586 | 0.097* | |
H22B | −0.1311 | 0.2753 | −0.3420 | 0.097* | |
H22C | −0.3290 | 0.3387 | −0.3578 | 0.097* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0653 (10) | 0.0610 (10) | 0.0601 (10) | −0.0203 (8) | −0.0208 (8) | 0.0153 (8) |
O2 | 0.0824 (12) | 0.0934 (12) | 0.0798 (12) | −0.0254 (10) | −0.0364 (10) | 0.0470 (10) |
O3 | 0.0627 (10) | 0.0669 (11) | 0.0774 (11) | −0.0259 (9) | −0.0218 (9) | 0.0279 (8) |
N1 | 0.1013 (18) | 0.0922 (17) | 0.0789 (16) | −0.0136 (14) | −0.0302 (13) | 0.0375 (13) |
N2 | 0.0756 (15) | 0.0687 (14) | 0.0825 (16) | −0.0277 (13) | −0.0195 (12) | 0.0177 (11) |
C1 | 0.0403 (13) | 0.0374 (12) | 0.0482 (14) | −0.0035 (10) | −0.0057 (10) | 0.0032 (10) |
C2 | 0.0407 (12) | 0.0441 (13) | 0.0525 (14) | −0.0083 (11) | −0.0123 (10) | 0.0077 (11) |
C3 | 0.0410 (13) | 0.0394 (13) | 0.0433 (13) | −0.0029 (11) | −0.0048 (10) | 0.0026 (10) |
C4 | 0.0475 (13) | 0.0469 (13) | 0.0475 (14) | −0.0058 (11) | −0.0103 (10) | 0.0048 (10) |
C5 | 0.0420 (12) | 0.0426 (13) | 0.0491 (14) | −0.0069 (11) | −0.0102 (10) | 0.0045 (11) |
C6 | 0.0476 (13) | 0.0429 (13) | 0.0522 (14) | −0.0061 (11) | −0.0058 (11) | 0.0049 (10) |
C7 | 0.0481 (14) | 0.0435 (13) | 0.0456 (14) | −0.0073 (11) | −0.0057 (11) | 0.0067 (11) |
C8 | 0.0640 (16) | 0.0529 (15) | 0.0553 (16) | −0.0116 (13) | −0.0062 (13) | 0.0117 (12) |
C9 | 0.0630 (17) | 0.0448 (14) | 0.0518 (15) | −0.0117 (14) | −0.0068 (13) | 0.0146 (11) |
C10 | 0.0519 (14) | 0.0618 (15) | 0.0583 (15) | 0.0023 (12) | −0.0078 (11) | 0.0042 (12) |
C11 | 0.0547 (15) | 0.0636 (16) | 0.0747 (17) | −0.0155 (13) | −0.0174 (12) | 0.0084 (12) |
C12 | 0.0469 (13) | 0.0472 (14) | 0.0520 (15) | −0.0068 (11) | −0.0105 (11) | 0.0083 (11) |
C13 | 0.0453 (13) | 0.0494 (14) | 0.0481 (14) | −0.0037 (11) | −0.0074 (10) | 0.0073 (11) |
C14 | 0.0455 (13) | 0.0418 (13) | 0.0417 (13) | −0.0029 (11) | −0.0067 (11) | 0.0051 (10) |
C15 | 0.0532 (14) | 0.0430 (14) | 0.0436 (14) | −0.0089 (12) | −0.0031 (11) | 0.0075 (11) |
C16 | 0.0582 (15) | 0.0619 (15) | 0.0521 (15) | −0.0131 (13) | −0.0170 (12) | 0.0152 (12) |
C17 | 0.0612 (16) | 0.0659 (17) | 0.0460 (15) | −0.0013 (14) | −0.0162 (12) | 0.0155 (12) |
C18 | 0.0582 (15) | 0.0558 (15) | 0.0499 (14) | −0.0106 (13) | −0.0066 (12) | 0.0158 (11) |
C19 | 0.0477 (14) | 0.0503 (14) | 0.0458 (14) | −0.0051 (12) | −0.0051 (11) | 0.0064 (11) |
C20 | 0.0826 (18) | 0.0746 (17) | 0.0691 (17) | −0.0334 (15) | −0.0242 (14) | 0.0087 (13) |
C21 | 0.109 (2) | 0.099 (2) | 0.101 (2) | −0.0326 (19) | −0.0406 (17) | 0.0647 (18) |
C22 | 0.0667 (16) | 0.0614 (16) | 0.0664 (17) | −0.0221 (13) | −0.0029 (12) | 0.0067 (12) |
O1—C15 | 1.369 (2) | C10—H10B | 0.960 |
O1—C20 | 1.438 (2) | C10—H10C | 0.960 |
O2—C17 | 1.364 (2) | C11—H11A | 0.960 |
O2—C21 | 1.426 (2) | C11—H11B | 0.960 |
O3—C19 | 1.368 (2) | C11—H11C | 0.960 |
O3—C22 | 1.428 (2) | C12—C13 | 1.351 (2) |
N1—C8 | 1.137 (2) | C12—H12 | 0.930 |
N2—C9 | 1.147 (3) | C13—C14 | 1.447 (2) |
C1—C2 | 1.363 (2) | C13—H13 | 0.930 |
C1—C12 | 1.444 (3) | C14—C19 | 1.408 (2) |
C1—C6 | 1.496 (2) | C14—C15 | 1.413 (3) |
C2—C3 | 1.415 (2) | C15—C16 | 1.367 (2) |
C2—H2 | 0.9300 | C16—C17 | 1.381 (3) |
C3—C7 | 1.371 (2) | C16—H16 | 0.930 |
C3—C4 | 1.494 (3) | C17—C18 | 1.383 (3) |
C4—C5 | 1.531 (3) | C18—C19 | 1.387 (3) |
C4—H4A | 0.9700 | C18—H18 | 0.930 |
C4—H4B | 0.9700 | C20—H20A | 0.960 |
C5—C11 | 1.526 (2) | C20—H20B | 0.960 |
C5—C6 | 1.528 (2) | C20—H20C | 0.960 |
C5—C10 | 1.529 (3) | C21—H21A | 0.960 |
C6—H6A | 0.9700 | C21—H21B | 0.960 |
C6—H6B | 0.9700 | C21—H21C | 0.960 |
C7—C9 | 1.428 (3) | C22—H22A | 0.960 |
C7—C8 | 1.441 (3) | C22—H22B | 0.960 |
C10—H10A | 0.960 | C22—H22C | 0.960 |
C15—O1—C20 | 117.67 (16) | H11A—C11—H11C | 109.5 |
C17—O2—C21 | 118.81 (19) | H11B—C11—H11C | 109.5 |
C19—O3—C22 | 119.17 (16) | C13—C12—C1 | 125.62 (19) |
C2—C1—C12 | 119.46 (18) | C13—C12—H12 | 117.2 |
C2—C1—C6 | 118.78 (17) | C1—C12—H12 | 117.2 |
C12—C1—C6 | 121.75 (16) | C12—C13—C14 | 130.2 (2) |
C1—C2—C3 | 123.91 (19) | C12—C13—H13 | 114.9 |
C1—C2—H2 | 118.0 | C14—C13—H13 | 114.9 |
C3—C2—H2 | 118.0 | C19—C14—C15 | 115.25 (18) |
C7—C3—C2 | 121.28 (19) | C19—C14—C13 | 119.21 (19) |
C7—C3—C4 | 120.35 (18) | C15—C14—C13 | 125.53 (18) |
C2—C3—C4 | 118.36 (17) | C16—C15—O1 | 120.8 (2) |
C3—C4—C5 | 113.13 (16) | C16—C15—C14 | 122.74 (19) |
C3—C4—H4A | 109.0 | O1—C15—C14 | 116.45 (17) |
C5—C4—H4A | 109.0 | C15—C16—C17 | 119.4 (2) |
C3—C4—H4B | 109.0 | C15—C16—H16 | 120.3 |
C5—C4—H4B | 109.0 | C17—C16—H16 | 120.3 |
H4A—C4—H4B | 107.8 | O2—C17—C16 | 114.3 (2) |
C11—C5—C6 | 109.17 (16) | O2—C17—C18 | 124.5 (2) |
C11—C5—C10 | 109.66 (17) | C16—C17—C18 | 121.2 (2) |
C6—C5—C10 | 110.68 (17) | C17—C18—C19 | 118.3 (2) |
C11—C5—C4 | 109.04 (17) | C17—C18—H18 | 120.9 |
C6—C5—C4 | 108.26 (16) | C19—C18—H18 | 120.9 |
C10—C5—C4 | 110.00 (16) | O3—C19—C18 | 121.32 (19) |
C1—C6—C5 | 114.07 (15) | O3—C19—C14 | 115.64 (17) |
C1—C6—H6A | 108.7 | C18—C19—C14 | 123.0 (2) |
C5—C6—H6A | 108.7 | O1—C20—H20A | 109.5 |
C1—C6—H6B | 108.7 | O1—C20—H20B | 109.5 |
C5—C6—H6B | 108.7 | H20A—C20—H20B | 109.5 |
H6A—C6—H6B | 107.6 | O1—C20—H20C | 109.5 |
C3—C7—C9 | 122.09 (18) | H20A—C20—H20C | 109.5 |
C3—C7—C8 | 123.23 (19) | H20B—C20—H20C | 109.5 |
C9—C7—C8 | 114.62 (18) | O2—C21—H21A | 109.5 |
N1—C8—C7 | 177.8 (2) | O2—C21—H21B | 109.5 |
N2—C9—C7 | 178.4 (2) | H21A—C21—H21B | 109.5 |
C5—C10—H10A | 109.5 | O2—C21—H21C | 109.5 |
C5—C10—H10B | 109.5 | H21A—C21—H21C | 109.5 |
H10A—C10—H10B | 109.5 | H21B—C21—H21C | 109.5 |
C5—C10—H10C | 109.5 | O3—C22—H22A | 109.5 |
H10A—C10—H10C | 109.5 | O3—C22—H22B | 109.5 |
H10B—C10—H10C | 109.5 | H22A—C22—H22B | 109.5 |
C5—C11—H11A | 109.5 | O3—C22—H22C | 109.5 |
C5—C11—H11B | 109.5 | H22A—C22—H22C | 109.5 |
H11A—C11—H11B | 109.5 | H22B—C22—H22C | 109.5 |
C5—C11—H11C | 109.5 | ||
C12—C1—C2—C3 | −179.83 (19) | C20—O1—C15—C16 | 6.7 (3) |
C6—C1—C2—C3 | −0.8 (3) | C20—O1—C15—C14 | −174.00 (18) |
C1—C2—C3—C7 | −179.71 (19) | C19—C14—C15—C16 | −2.5 (3) |
C1—C2—C3—C4 | 1.7 (3) | C13—C14—C15—C16 | 176.5 (2) |
C7—C3—C4—C5 | 152.78 (19) | C19—C14—C15—O1 | 178.29 (17) |
C2—C3—C4—C5 | −28.6 (3) | C13—C14—C15—O1 | −2.8 (3) |
C3—C4—C5—C11 | 170.40 (16) | O1—C15—C16—C17 | −179.68 (18) |
C3—C4—C5—C6 | 51.7 (2) | C14—C15—C16—C17 | 1.1 (3) |
C3—C4—C5—C10 | −69.3 (2) | C21—O2—C17—C16 | −178.6 (2) |
C2—C1—C6—C5 | 27.2 (3) | C21—O2—C17—C18 | 1.3 (4) |
C12—C1—C6—C5 | −153.78 (18) | C15—C16—C17—O2 | −179.2 (2) |
C11—C5—C6—C1 | −169.97 (17) | C15—C16—C17—C18 | 0.8 (3) |
C10—C5—C6—C1 | 69.2 (2) | O2—C17—C18—C19 | 178.9 (2) |
C4—C5—C6—C1 | −51.4 (2) | C16—C17—C18—C19 | −1.2 (3) |
C2—C3—C7—C9 | −2.4 (3) | C22—O3—C19—C18 | 6.0 (3) |
C4—C3—C7—C9 | 176.24 (19) | C22—O3—C19—C14 | −174.54 (18) |
C2—C3—C7—C8 | −179.4 (2) | C17—C18—C19—O3 | 179.05 (19) |
C4—C3—C7—C8 | −0.7 (3) | C17—C18—C19—C14 | −0.3 (3) |
C2—C1—C12—C13 | 177.44 (19) | C15—C14—C19—O3 | −177.34 (18) |
C6—C1—C12—C13 | −1.5 (3) | C13—C14—C19—O3 | 3.7 (3) |
C1—C12—C13—C14 | −178.5 (2) | C15—C14—C19—C18 | 2.1 (3) |
C12—C13—C14—C19 | 179.6 (2) | C13—C14—C19—C18 | −176.9 (2) |
C12—C13—C14—C15 | 0.7 (4) |
Experimental details
Crystal data | |
Chemical formula | C22H24N2O3 |
Mr | 364.43 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 291 |
a, b, c (Å) | 7.5983 (3), 11.4757 (4), 11.5774 (4) |
α, β, γ (°) | 84.8457 (15), 82.2149 (16), 79.0257 (17) |
V (Å3) | 979.77 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.25 × 0.23 × 0.23 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8836, 4334, 1655 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.647 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.118, 0.90 |
No. of reflections | 4334 |
No. of parameters | 249 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.13, −0.15 |
Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK, SHELXS97 (Sheldrick, 1990), SHELXTL-Plus (Sheldrick, 1991), SHELXL97 (Sheldrick, 1997), PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).
No Comment