Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024457/hb2089sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024457/hb2089Isup2.hkl |
CCDC reference: 613703
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).
C23H27N3O2 | Dx = 1.190 Mg m−3 |
Mr = 377.48 | Melting point: 438 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 6889 reflections |
a = 8.2388 (7) Å | θ = 2.2–23.7° |
b = 19.9018 (17) Å | µ = 0.08 mm−1 |
c = 25.697 (2) Å | T = 292 K |
V = 4213.4 (6) Å3 | Block, colorless |
Z = 8 | 0.30 × 0.20 × 0.10 mm |
F(000) = 1616 |
Bruker SMART CCD diffractometer | 5130 independent reflections |
Radiation source: fine-focus sealed tube | 3292 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
ω scans | θmax = 28.3°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −10→10 |
Tmin = 0.977, Tmax = 0.992 | k = −25→25 |
40947 measured reflections | l = −33→33 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0891P)2] where P = (Fo2 + 2Fc2)/3 |
5130 reflections | (Δ/σ)max = 0.001 |
285 parameters | Δρmax = 0.22 e Å−3 |
6 restraints | Δρmin = −0.28 e Å−3 |
Experimental. 1H NMR (CDCl3, 200 MHz): δ 0.78 (t, 6H, 2CH3, J = 7.0 Hz), 1.50–1.62 (m, 4H, 2CH2), 3.23 (t, 4H, 2NCH2, J = 6.8 Hz), 3.82 (s, 3H, OCH3), 6.72 (s, 1H, ═CH), 6.87–8.07 (m, 9H, Ar—H). MS (EI 70 eV) m/z(%): 377 (M+). |
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 | Occ. (<1) | |
C1 | 0.3033 (3) | 0.24871 (11) | 0.23220 (8) | 0.0795 (7) | |
H1A | 0.1923 | 0.2340 | 0.2315 | 0.119* | |
H1B | 0.3358 | 0.2619 | 0.1978 | 0.119* | |
H1C | 0.3138 | 0.2863 | 0.2554 | 0.119* | |
C2 | 0.3773 (2) | 0.17042 (9) | 0.29855 (6) | 0.0502 (4) | |
C3 | 0.4901 (2) | 0.12404 (10) | 0.31604 (7) | 0.0582 (5) | |
H3 | 0.5765 | 0.1118 | 0.2948 | 0.070* | |
C4 | 0.4749 (2) | 0.09599 (9) | 0.36461 (6) | 0.0514 (4) | |
H4 | 0.5524 | 0.0654 | 0.3761 | 0.062* | |
C5 | 0.34472 (18) | 0.11270 (7) | 0.39710 (6) | 0.0407 (4) | |
C6 | 0.2336 (2) | 0.15936 (8) | 0.37881 (6) | 0.0476 (4) | |
H6 | 0.1466 | 0.1716 | 0.3998 | 0.057* | |
C7 | 0.2490 (2) | 0.18825 (8) | 0.33011 (6) | 0.0507 (4) | |
H7 | 0.1731 | 0.2196 | 0.3187 | 0.061* | |
C8 | 0.33305 (19) | 0.08033 (8) | 0.44784 (6) | 0.0433 (4) | |
H8 | 0.4224 | 0.0546 | 0.4575 | 0.052* | |
C9 | 0.21111 (19) | 0.08240 (7) | 0.48274 (6) | 0.0396 (4) | |
C10 | 0.21958 (19) | 0.04634 (8) | 0.53277 (6) | 0.0433 (4) | |
C11 | 0.05178 (19) | 0.04857 (8) | 0.61185 (5) | 0.0416 (4) | |
C12 | 0.0372 (2) | −0.01662 (9) | 0.62872 (7) | 0.0571 (5) | |
H12 | 0.0338 | −0.0517 | 0.6048 | 0.068* | |
C13 | 0.0278 (3) | −0.02978 (11) | 0.68124 (7) | 0.0790 (7) | |
H13 | 0.0182 | −0.0739 | 0.6928 | 0.095* | |
C14 | 0.0325 (3) | 0.02186 (11) | 0.71656 (7) | 0.0855 (7) | |
H14 | 0.0259 | 0.0128 | 0.7520 | 0.103* | |
C15 | 0.0470 (3) | 0.08664 (11) | 0.69965 (7) | 0.0824 (7) | |
H15 | 0.0500 | 0.1216 | 0.7236 | 0.099* | |
C16 | 0.0574 (2) | 0.10036 (9) | 0.64684 (7) | 0.0607 (5) | |
H16 | 0.0680 | 0.1444 | 0.6353 | 0.073* | |
C17 | −0.0147 (2) | 0.10276 (8) | 0.52269 (6) | 0.0438 (4) | |
C18 | −0.2796 (2) | 0.09601 (9) | 0.56884 (6) | 0.0561 (5) | |
H18A | −0.2274 | 0.0587 | 0.5864 | 0.067* | |
H18B | −0.3708 | 0.0782 | 0.5494 | 0.067* | |
C19 | −0.3418 (3) | 0.14440 (10) | 0.60886 (8) | 0.0713 (6) | |
H19A | −0.4058 | 0.1790 | 0.5919 | 0.086* | |
H19B | −0.2510 | 0.1659 | 0.6262 | 0.086* | |
C20 | −0.4452 (3) | 0.10827 (13) | 0.64866 (9) | 0.0997 (9) | |
H20A | −0.5334 | 0.0860 | 0.6314 | 0.150* | |
H20B | −0.4875 | 0.1402 | 0.6732 | 0.150* | |
H20C | −0.3802 | 0.0757 | 0.6667 | 0.150* | |
C21 | −0.2512 (3) | 0.15675 (15) | 0.48652 (11) | 0.0501 (9) | 0.677 (5) |
H21A | −0.2248 | 0.1323 | 0.4550 | 0.060* | 0.677 (5) |
H21B | −0.3677 | 0.1550 | 0.4917 | 0.060* | 0.677 (5) |
C22 | −0.1955 (4) | 0.22843 (15) | 0.48227 (13) | 0.0603 (9) | 0.677 (5) |
H22A | −0.0778 | 0.2300 | 0.4817 | 0.072* | 0.677 (5) |
H22B | −0.2328 | 0.2537 | 0.5123 | 0.072* | 0.677 (5) |
C23 | −0.2624 (8) | 0.2597 (3) | 0.4329 (2) | 0.0805 (15) | 0.677 (5) |
H23A | −0.2264 | 0.2343 | 0.4033 | 0.121* | 0.677 (5) |
H23B | −0.2242 | 0.3052 | 0.4299 | 0.121* | 0.677 (5) |
H23C | −0.3788 | 0.2596 | 0.4341 | 0.121* | 0.677 (5) |
C21' | −0.1943 (7) | 0.1976 (3) | 0.5070 (2) | 0.0451 (16) | 0.323 (5) |
H21C | −0.2568 | 0.2264 | 0.5299 | 0.054* | 0.323 (5) |
H21D | −0.0924 | 0.2195 | 0.4987 | 0.054* | 0.323 (5) |
C22' | −0.2895 (8) | 0.1804 (3) | 0.4579 (2) | 0.0561 (18) | 0.323 (5) |
H22C | −0.2334 | 0.1446 | 0.4398 | 0.067* | 0.323 (5) |
H22D | −0.3953 | 0.1635 | 0.4680 | 0.067* | 0.323 (5) |
C23' | −0.3131 (19) | 0.2378 (4) | 0.4210 (5) | 0.077 (3) | 0.323 (5) |
H23D | −0.3643 | 0.2745 | 0.4389 | 0.116* | 0.323 (5) |
H23E | −0.3805 | 0.2237 | 0.3925 | 0.116* | 0.323 (5) |
H23F | −0.2096 | 0.2521 | 0.4078 | 0.116* | 0.323 (5) |
N1 | 0.06302 (16) | 0.11546 (7) | 0.47960 (5) | 0.0479 (4) | |
N2 | 0.07157 (15) | 0.06132 (6) | 0.55712 (4) | 0.0412 (3) | |
N3 | −0.16450 (18) | 0.12609 (10) | 0.53256 (6) | 0.0720 (5) | |
O1 | 0.40308 (17) | 0.19569 (7) | 0.24956 (5) | 0.0728 (4) | |
O2 | 0.32543 (15) | 0.01202 (7) | 0.55148 (5) | 0.0680 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0839 (16) | 0.0946 (16) | 0.0600 (12) | −0.0145 (13) | −0.0054 (11) | 0.0335 (11) |
C2 | 0.0574 (11) | 0.0576 (10) | 0.0355 (8) | −0.0049 (8) | 0.0033 (8) | 0.0047 (7) |
C3 | 0.0590 (11) | 0.0703 (12) | 0.0454 (10) | 0.0095 (9) | 0.0171 (8) | 0.0016 (9) |
C4 | 0.0519 (10) | 0.0556 (10) | 0.0466 (10) | 0.0107 (8) | 0.0093 (8) | 0.0029 (8) |
C5 | 0.0434 (9) | 0.0403 (8) | 0.0385 (8) | 0.0016 (7) | 0.0037 (7) | 0.0010 (6) |
C6 | 0.0495 (10) | 0.0514 (9) | 0.0419 (9) | 0.0058 (8) | 0.0087 (7) | 0.0028 (7) |
C7 | 0.0519 (10) | 0.0531 (10) | 0.0473 (9) | 0.0052 (8) | 0.0017 (8) | 0.0104 (7) |
C8 | 0.0423 (9) | 0.0444 (8) | 0.0432 (9) | 0.0074 (7) | 0.0020 (7) | 0.0036 (7) |
C9 | 0.0421 (9) | 0.0415 (8) | 0.0351 (8) | 0.0046 (7) | 0.0015 (6) | 0.0035 (6) |
C10 | 0.0431 (9) | 0.0459 (9) | 0.0408 (8) | 0.0066 (7) | 0.0013 (7) | 0.0064 (7) |
C11 | 0.0453 (9) | 0.0468 (9) | 0.0326 (8) | −0.0011 (7) | 0.0003 (7) | 0.0063 (7) |
C12 | 0.0823 (14) | 0.0478 (10) | 0.0411 (9) | −0.0059 (9) | −0.0025 (9) | 0.0038 (7) |
C13 | 0.129 (2) | 0.0619 (12) | 0.0460 (11) | −0.0156 (12) | −0.0026 (12) | 0.0189 (10) |
C14 | 0.141 (2) | 0.0832 (15) | 0.0325 (10) | −0.0243 (14) | −0.0034 (12) | 0.0089 (10) |
C15 | 0.132 (2) | 0.0727 (14) | 0.0429 (11) | −0.0230 (13) | 0.0050 (12) | −0.0111 (10) |
C16 | 0.0863 (15) | 0.0502 (10) | 0.0455 (10) | −0.0109 (9) | 0.0041 (9) | 0.0015 (8) |
C17 | 0.0441 (9) | 0.0515 (9) | 0.0359 (8) | 0.0111 (7) | 0.0031 (7) | 0.0070 (7) |
C18 | 0.0484 (10) | 0.0693 (12) | 0.0506 (10) | 0.0097 (9) | 0.0052 (8) | 0.0003 (8) |
C19 | 0.0754 (14) | 0.0700 (13) | 0.0685 (13) | 0.0124 (10) | 0.0206 (11) | −0.0014 (10) |
C20 | 0.109 (2) | 0.116 (2) | 0.0732 (15) | 0.0156 (15) | 0.0492 (14) | 0.0065 (14) |
C21 | 0.0407 (15) | 0.0602 (18) | 0.0495 (18) | 0.0076 (13) | 0.0011 (13) | 0.0035 (14) |
C22 | 0.0610 (18) | 0.0544 (19) | 0.066 (2) | 0.0123 (14) | 0.0016 (15) | 0.0066 (16) |
C23 | 0.098 (4) | 0.076 (3) | 0.068 (3) | 0.023 (3) | 0.000 (2) | 0.024 (3) |
C21' | 0.050 (3) | 0.030 (3) | 0.056 (4) | 0.007 (2) | 0.008 (3) | 0.007 (3) |
C22' | 0.070 (4) | 0.052 (3) | 0.046 (4) | 0.016 (3) | −0.017 (3) | 0.011 (3) |
C23' | 0.116 (10) | 0.060 (6) | 0.056 (5) | −0.002 (5) | −0.018 (4) | 0.014 (4) |
N1 | 0.0469 (8) | 0.0602 (9) | 0.0367 (7) | 0.0153 (6) | 0.0067 (6) | 0.0109 (6) |
N2 | 0.0443 (8) | 0.0462 (7) | 0.0331 (7) | 0.0070 (6) | 0.0027 (6) | 0.0077 (5) |
N3 | 0.0568 (10) | 0.1049 (13) | 0.0543 (9) | 0.0387 (9) | 0.0217 (7) | 0.0393 (9) |
O1 | 0.0783 (10) | 0.0964 (10) | 0.0437 (7) | 0.0067 (8) | 0.0129 (6) | 0.0205 (7) |
O2 | 0.0565 (8) | 0.0861 (9) | 0.0613 (8) | 0.0287 (7) | 0.0074 (6) | 0.0307 (7) |
C1—O1 | 1.410 (2) | C17—N1 | 1.3038 (18) |
C1—H1A | 0.9600 | C17—N3 | 1.343 (2) |
C1—H1B | 0.9600 | C17—N2 | 1.4027 (19) |
C1—H1C | 0.9600 | C18—N3 | 1.458 (2) |
C2—O1 | 1.3722 (18) | C18—C19 | 1.499 (2) |
C2—C7 | 1.379 (2) | C18—H18A | 0.9700 |
C2—C3 | 1.385 (2) | C18—H18B | 0.9700 |
C3—C4 | 1.373 (2) | C19—C20 | 1.513 (3) |
C3—H3 | 0.9300 | C19—H19A | 0.9700 |
C4—C5 | 1.399 (2) | C19—H19B | 0.9700 |
C4—H4 | 0.9300 | C20—H20A | 0.9600 |
C5—C6 | 1.386 (2) | C20—H20B | 0.9600 |
C5—C8 | 1.457 (2) | C20—H20C | 0.9600 |
C6—C7 | 1.383 (2) | C21—C22 | 1.503 (4) |
C6—H6 | 0.9300 | C21—N3 | 1.510 (3) |
C7—H7 | 0.9300 | C21—H21A | 0.9700 |
C8—C9 | 1.347 (2) | C21—H21B | 0.9700 |
C8—H8 | 0.9300 | C22—C23 | 1.518 (5) |
C9—N1 | 1.388 (2) | C22—H22A | 0.9700 |
C9—C10 | 1.474 (2) | C22—H22B | 0.9700 |
C10—O2 | 1.2076 (18) | C23—H23A | 0.9600 |
C10—N2 | 1.403 (2) | C23—H23B | 0.9600 |
C11—C16 | 1.369 (2) | C23—H23C | 0.9600 |
C11—C12 | 1.373 (2) | C21'—C22' | 1.525 (7) |
C11—N2 | 1.4383 (18) | C21'—N3 | 1.586 (5) |
C12—C13 | 1.377 (2) | C21'—H21C | 0.9700 |
C12—H12 | 0.9300 | C21'—H21D | 0.9700 |
C13—C14 | 1.372 (3) | C22'—C23' | 1.499 (8) |
C13—H13 | 0.9300 | C22'—H22C | 0.9700 |
C14—C15 | 1.366 (3) | C22'—H22D | 0.9700 |
C14—H14 | 0.9300 | C23'—H23D | 0.9600 |
C15—C16 | 1.387 (2) | C23'—H23E | 0.9600 |
C15—H15 | 0.9300 | C23'—H23F | 0.9600 |
C16—H16 | 0.9300 | ||
O1—C1—H1A | 109.5 | N3—C18—H18B | 108.9 |
O1—C1—H1B | 109.5 | C19—C18—H18B | 108.9 |
H1A—C1—H1B | 109.5 | H18A—C18—H18B | 107.7 |
O1—C1—H1C | 109.5 | C18—C19—C20 | 110.53 (18) |
H1A—C1—H1C | 109.5 | C18—C19—H19A | 109.5 |
H1B—C1—H1C | 109.5 | C20—C19—H19A | 109.5 |
O1—C2—C7 | 124.33 (16) | C18—C19—H19B | 109.5 |
O1—C2—C3 | 115.98 (16) | C20—C19—H19B | 109.5 |
C7—C2—C3 | 119.69 (15) | H19A—C19—H19B | 108.1 |
C4—C3—C2 | 120.33 (16) | C19—C20—H20A | 109.5 |
C4—C3—H3 | 119.8 | C19—C20—H20B | 109.5 |
C2—C3—H3 | 119.8 | H20A—C20—H20B | 109.5 |
C3—C4—C5 | 121.03 (16) | C19—C20—H20C | 109.5 |
C3—C4—H4 | 119.5 | H20A—C20—H20C | 109.5 |
C5—C4—H4 | 119.5 | H20B—C20—H20C | 109.5 |
C6—C5—C4 | 117.58 (14) | C22—C21—N3 | 107.2 (2) |
C6—C5—C8 | 123.78 (14) | C22—C21—H21A | 110.3 |
C4—C5—C8 | 118.64 (14) | N3—C21—H21A | 110.3 |
C7—C6—C5 | 121.69 (15) | C22—C21—H21B | 110.3 |
C7—C6—H6 | 119.2 | N3—C21—H21B | 110.3 |
C5—C6—H6 | 119.2 | H21A—C21—H21B | 108.5 |
C2—C7—C6 | 119.67 (16) | C21—C22—C23 | 109.9 (3) |
C2—C7—H7 | 120.2 | C21—C22—H22A | 109.7 |
C6—C7—H7 | 120.2 | C23—C22—H22A | 109.7 |
C9—C8—C5 | 129.13 (15) | C21—C22—H22B | 109.7 |
C9—C8—H8 | 115.4 | C23—C22—H22B | 109.7 |
C5—C8—H8 | 115.4 | H22A—C22—H22B | 108.2 |
C8—C9—N1 | 129.13 (14) | C22'—C21'—N3 | 102.7 (4) |
C8—C9—C10 | 122.03 (14) | C22'—C21'—H21C | 111.2 |
N1—C9—C10 | 108.84 (12) | N3—C21'—H21C | 111.2 |
O2—C10—N2 | 124.79 (14) | C22'—C21'—H21D | 111.2 |
O2—C10—C9 | 131.06 (15) | N3—C21'—H21D | 111.2 |
N2—C10—C9 | 104.15 (12) | H21C—C21'—H21D | 109.1 |
C16—C11—C12 | 120.47 (15) | C23'—C22'—C21' | 114.8 (6) |
C16—C11—N2 | 120.38 (14) | C23'—C22'—H22C | 108.6 |
C12—C11—N2 | 119.03 (14) | C21'—C22'—H22C | 108.6 |
C11—C12—C13 | 119.61 (17) | C23'—C22'—H22D | 108.6 |
C11—C12—H12 | 120.2 | C21'—C22'—H22D | 108.6 |
C13—C12—H12 | 120.2 | H22C—C22'—H22D | 107.5 |
C14—C13—C12 | 120.29 (18) | C22'—C23'—H23D | 109.5 |
C14—C13—H13 | 119.9 | C22'—C23'—H23E | 109.5 |
C12—C13—H13 | 119.9 | H23D—C23'—H23E | 109.5 |
C15—C14—C13 | 119.96 (18) | C22'—C23'—H23F | 109.5 |
C15—C14—H14 | 120.0 | H23D—C23'—H23F | 109.5 |
C13—C14—H14 | 120.0 | H23E—C23'—H23F | 109.5 |
C14—C15—C16 | 120.17 (18) | C17—N1—C9 | 106.87 (12) |
C14—C15—H15 | 119.9 | C10—N2—C17 | 106.50 (12) |
C16—C15—H15 | 119.9 | C10—N2—C11 | 119.81 (12) |
C11—C16—C15 | 119.51 (17) | C17—N2—C11 | 131.53 (13) |
C11—C16—H16 | 120.2 | C17—N3—C18 | 125.19 (15) |
C15—C16—H16 | 120.2 | C17—N3—C21 | 115.23 (15) |
N1—C17—N3 | 122.99 (14) | C18—N3—C21 | 111.05 (16) |
N1—C17—N2 | 113.64 (13) | C17—N3—C21' | 112.0 (2) |
N3—C17—N2 | 123.35 (14) | C18—N3—C21' | 122.2 (2) |
N3—C18—C19 | 113.39 (16) | C21—N3—C21' | 40.6 (2) |
N3—C18—H18A | 108.9 | C2—O1—C1 | 118.31 (15) |
C19—C18—H18A | 108.9 | ||
O1—C2—C3—C4 | 179.86 (17) | C8—C9—N1—C17 | 179.99 (17) |
C7—C2—C3—C4 | −0.2 (3) | C10—C9—N1—C17 | 0.46 (18) |
C2—C3—C4—C5 | 1.0 (3) | O2—C10—N2—C17 | 179.36 (17) |
C3—C4—C5—C6 | −1.1 (3) | C9—C10—N2—C17 | 0.38 (16) |
C3—C4—C5—C8 | 178.78 (16) | O2—C10—N2—C11 | 14.2 (2) |
C4—C5—C6—C7 | 0.5 (2) | C9—C10—N2—C11 | −164.78 (13) |
C8—C5—C6—C7 | −179.34 (16) | N1—C17—N2—C10 | −0.12 (19) |
O1—C2—C7—C6 | 179.57 (16) | N3—C17—N2—C10 | 178.54 (17) |
C3—C2—C7—C6 | −0.4 (3) | N1—C17—N2—C11 | 162.61 (15) |
C5—C6—C7—C2 | 0.2 (3) | N3—C17—N2—C11 | −18.7 (3) |
C6—C5—C8—C9 | 8.3 (3) | C16—C11—N2—C10 | 103.32 (18) |
C4—C5—C8—C9 | −171.60 (16) | C12—C11—N2—C10 | −72.7 (2) |
C5—C8—C9—N1 | 0.6 (3) | C16—C11—N2—C17 | −57.5 (2) |
C5—C8—C9—C10 | −179.91 (15) | C12—C11—N2—C17 | 126.43 (19) |
C8—C9—C10—O2 | 1.0 (3) | N1—C17—N3—C18 | 156.36 (17) |
N1—C9—C10—O2 | −179.41 (18) | N2—C17—N3—C18 | −22.2 (3) |
C8—C9—C10—N2 | 179.91 (14) | N1—C17—N3—C21 | 11.5 (3) |
N1—C9—C10—N2 | −0.52 (17) | N2—C17—N3—C21 | −167.08 (18) |
C16—C11—C12—C13 | 0.2 (3) | N1—C17—N3—C21' | −32.9 (3) |
N2—C11—C12—C13 | 176.20 (19) | N2—C17—N3—C21' | 148.6 (3) |
C11—C12—C13—C14 | 0.1 (4) | C19—C18—N3—C17 | 125.6 (2) |
C12—C13—C14—C15 | −0.1 (4) | C19—C18—N3—C21 | −88.2 (2) |
C13—C14—C15—C16 | −0.2 (4) | C19—C18—N3—C21' | −44.2 (3) |
C12—C11—C16—C15 | −0.5 (3) | C22—C21—N3—C17 | −83.9 (3) |
N2—C11—C16—C15 | −176.45 (19) | C22—C21—N3—C18 | 126.4 (2) |
C14—C15—C16—C11 | 0.5 (3) | C22—C21—N3—C21' | 11.1 (3) |
N3—C18—C19—C20 | −173.62 (18) | C22'—C21'—N3—C17 | 100.0 (4) |
N3—C21—C22—C23 | 173.2 (3) | C22'—C21'—N3—C18 | −89.0 (4) |
N3—C21'—C22'—C23' | −170.8 (8) | C22'—C21'—N3—C21 | −3.7 (3) |
N3—C17—N1—C9 | −178.89 (18) | C7—C2—O1—C1 | 7.4 (3) |
N2—C17—N1—C9 | −0.22 (19) | C3—C2—O1—C1 | −172.70 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O2i | 0.93 | 2.48 | 3.361 (2) | 159 |
C6—H6···N1 | 0.93 | 2.43 | 3.074 (2) | 126 |
C1—H1A···O1ii | 0.96 | 2.55 | 3.493 (3) | 168 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1/2, y, −z+1/2. |