Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805004861/rz6051sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805004861/rz6051Isup2.hkl |
CCDC reference: 269858
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C22H18N2O3 | Z = 2 |
Mr = 358.38 | F(000) = 376 |
Triclinic, P1 | Dx = 1.313 Mg m−3 |
Hall symbol: -P 1 | Melting point = 447–448 K |
a = 8.8670 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.7248 (13) Å | Cell parameters from 2107 reflections |
c = 11.2270 (15) Å | θ = 2.4–28.1° |
α = 101.006 (2)° | µ = 0.09 mm−1 |
β = 105.841 (2)° | T = 293 K |
γ = 93.966 (2)° | Block, colourless |
V = 906.6 (2) Å3 | 0.26 × 0.24 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 3176 independent reflections |
Radiation source: fine-focus sealed tube | 2468 reflections with I > 2s(I) |
Graphite monochromator | Rint = 0.014 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −10→10 |
Tmin = 0.965, Tmax = 0.983 | k = −11→7 |
4966 measured reflections | l = −12→13 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0583P)2 + 0.0577P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.104 | (Δ/σ)max = 0.002 |
S = 1.06 | Δρmax = 0.13 e Å−3 |
3176 reflections | Δρmin = −0.13 e Å−3 |
271 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 | Occ. (<1) | |
N1 | 1.27945 (14) | 0.71605 (13) | 0.64337 (11) | 0.0631 (3) | |
N2 | 1.22726 (14) | 0.83031 (13) | 0.70996 (11) | 0.0626 (4) | |
O1 | 1.04312 (10) | 0.74286 (9) | 0.52981 (8) | 0.0489 (3) | |
O2 | 0.93157 (11) | 0.37714 (10) | 0.10900 (9) | 0.0596 (3) | |
O3 | 1.16964 (11) | 0.23716 (10) | 0.13210 (9) | 0.0626 (3) | |
C1 | 1.08861 (16) | 0.84236 (14) | 0.64049 (12) | 0.0502 (3) | |
C2 | 1.16831 (15) | 0.66835 (14) | 0.53855 (13) | 0.0488 (3) | |
C3 | 0.98479 (16) | 0.94660 (15) | 0.66452 (12) | 0.0519 (4) | |
C4 | 0.84722 (18) | 0.95434 (16) | 0.57398 (14) | 0.0607 (4) | |
H4 | 0.8174 | 0.8898 | 0.4964 | 0.073* | |
C5 | 0.7531 (2) | 1.05758 (19) | 0.59773 (18) | 0.0736 (5) | |
H5 | 0.6604 | 1.0628 | 0.5361 | 0.088* | |
C6 | 0.7967 (2) | 1.15252 (18) | 0.71271 (19) | 0.0785 (5) | |
H6 | 0.7339 | 1.2224 | 0.7286 | 0.094* | |
C7 | 0.9322 (2) | 1.14451 (19) | 0.80367 (18) | 0.0813 (5) | |
H7 | 0.9606 | 1.2083 | 0.8816 | 0.098* | |
C8 | 1.02623 (19) | 1.04305 (17) | 0.78066 (15) | 0.0701 (5) | |
H8 | 1.1185 | 1.0384 | 0.8430 | 0.084* | |
C9 | 1.16559 (15) | 0.55251 (14) | 0.43469 (12) | 0.0484 (3) | |
C10 | 1.04277 (15) | 0.52309 (14) | 0.32138 (13) | 0.0497 (3) | |
H10 | 0.9588 | 0.5763 | 0.3125 | 0.060* | |
C11 | 1.04536 (15) | 0.41565 (14) | 0.22275 (13) | 0.0484 (3) | |
C12 | 1.17413 (15) | 0.33716 (14) | 0.23554 (13) | 0.0498 (3) | |
C13 | 1.29419 (16) | 0.36621 (15) | 0.34832 (14) | 0.0556 (4) | |
H13 | 1.3788 | 0.3138 | 0.3576 | 0.067* | |
C14 | 1.28950 (16) | 0.47260 (15) | 0.44750 (13) | 0.0543 (4) | |
H14 | 1.3704 | 0.4906 | 0.5235 | 0.065* | |
C15 | 0.79243 (14) | 0.44583 (15) | 0.09707 (12) | 0.0643 (4) | |
H15A | 0.8133 | 0.5408 | 0.0877 | 0.077* | 0.750 (8) |
H15B | 0.7588 | 0.4493 | 0.1718 | 0.077* | 0.750 (8) |
H15C | 0.8175 | 0.5445 | 0.1008 | 0.077* | 0.250 (8) |
H15D | 0.7504 | 0.4371 | 0.1659 | 0.077* | 0.250 (8) |
C16 | 0.66486 (13) | 0.36181 (18) | −0.01656 (12) | 0.0438 (9) | 0.750 (8) |
C17 | 0.5910 (2) | 0.4238 (3) | −0.11515 (12) | 0.0585 (9) | 0.750 (8) |
H17A | 0.6238 | 0.5173 | −0.1134 | 0.070* | 0.750 (8) |
C18 | 0.46808 (17) | 0.3462 (4) | −0.21638 (11) | 0.0733 (12) | 0.750 (8) |
H18A | 0.4187 | 0.3877 | −0.2823 | 0.088* | 0.750 (8) |
C19 | 0.41907 (15) | 0.2064 (4) | −0.21902 (17) | 0.0664 (12) | 0.750 (8) |
H19A | 0.3368 | 0.1544 | −0.2868 | 0.080* | 0.750 (8) |
C20 | 0.4929 (2) | 0.1444 (3) | −0.1204 (2) | 0.0591 (9) | 0.750 (8) |
H20A | 0.4602 | 0.0509 | −0.1222 | 0.071* | 0.750 (8) |
C21 | 0.61584 (19) | 0.22208 (19) | −0.0192 (2) | 0.0512 (8) | 0.750 (8) |
H21A | 0.6653 | 0.1806 | 0.0468 | 0.061* | 0.750 (8) |
C16' | 0.67154 (14) | 0.37769 (18) | −0.02568 (12) | 0.063 (4) | 0.250 (8) |
C17' | 0.6129 (2) | 0.4580 (3) | −0.11393 (15) | 0.085 (4) | 0.250 (8) |
H17B | 0.6602 | 0.5498 | −0.1028 | 0.102* | 0.250 (8) |
C18' | 0.4837 (2) | 0.4011 (4) | −0.21881 (13) | 0.127 (6) | 0.250 (8) |
H18B | 0.4445 | 0.4548 | −0.2779 | 0.153* | 0.250 (8) |
C19' | 0.41314 (14) | 0.2639 (4) | −0.23544 (14) | 0.113 (7) | 0.250 (8) |
H19B | 0.3267 | 0.2259 | −0.3056 | 0.135* | 0.250 (8) |
C20' | 0.47175 (17) | 0.1836 (3) | −0.1472 (2) | 0.060 (3) | 0.250 (8) |
H20B | 0.4245 | 0.0918 | −0.1583 | 0.072* | 0.250 (8) |
C21' | 0.60095 (16) | 0.24050 (19) | −0.04231 (18) | 0.053 (3) | 0.250 (8) |
H21B | 0.6402 | 0.1868 | 0.0167 | 0.064* | 0.250 (8) |
C22 | 1.29677 (19) | 0.15388 (18) | 0.14242 (16) | 0.0723 (5) | |
H22A | 1.3932 | 0.2131 | 0.1541 | 0.108* | |
H22B | 1.2759 | 0.0818 | 0.0664 | 0.108* | |
H22C | 1.3069 | 0.1106 | 0.2138 | 0.108* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0522 (7) | 0.0675 (8) | 0.0542 (7) | 0.0018 (6) | 0.0017 (6) | −0.0012 (6) |
N2 | 0.0563 (7) | 0.0683 (8) | 0.0482 (7) | 0.0006 (6) | 0.0034 (6) | −0.0030 (6) |
O1 | 0.0438 (5) | 0.0525 (5) | 0.0421 (5) | −0.0030 (4) | 0.0078 (4) | 0.0010 (4) |
O2 | 0.0434 (5) | 0.0661 (6) | 0.0540 (6) | 0.0114 (4) | 0.0029 (4) | −0.0086 (5) |
O3 | 0.0556 (6) | 0.0643 (6) | 0.0624 (6) | 0.0163 (5) | 0.0157 (5) | −0.0004 (5) |
C1 | 0.0496 (8) | 0.0532 (8) | 0.0390 (7) | −0.0086 (6) | 0.0088 (6) | 0.0004 (6) |
C2 | 0.0405 (7) | 0.0522 (8) | 0.0483 (8) | −0.0014 (6) | 0.0090 (6) | 0.0067 (6) |
C3 | 0.0532 (8) | 0.0537 (8) | 0.0455 (7) | −0.0064 (6) | 0.0179 (6) | 0.0026 (6) |
C4 | 0.0639 (9) | 0.0655 (9) | 0.0514 (8) | 0.0043 (7) | 0.0177 (7) | 0.0095 (7) |
C5 | 0.0711 (10) | 0.0808 (11) | 0.0806 (12) | 0.0168 (9) | 0.0319 (9) | 0.0287 (10) |
C6 | 0.0888 (13) | 0.0636 (10) | 0.1001 (14) | 0.0109 (9) | 0.0581 (12) | 0.0140 (10) |
C7 | 0.0855 (13) | 0.0718 (11) | 0.0810 (12) | −0.0069 (10) | 0.0419 (11) | −0.0161 (9) |
C8 | 0.0636 (9) | 0.0763 (11) | 0.0590 (9) | −0.0074 (8) | 0.0205 (8) | −0.0108 (8) |
C9 | 0.0416 (7) | 0.0491 (7) | 0.0498 (8) | −0.0045 (6) | 0.0109 (6) | 0.0067 (6) |
C10 | 0.0393 (7) | 0.0491 (7) | 0.0544 (8) | 0.0028 (6) | 0.0098 (6) | 0.0027 (6) |
C11 | 0.0379 (7) | 0.0496 (7) | 0.0506 (8) | −0.0011 (6) | 0.0085 (6) | 0.0024 (6) |
C12 | 0.0436 (7) | 0.0491 (8) | 0.0549 (8) | 0.0021 (6) | 0.0163 (6) | 0.0056 (6) |
C13 | 0.0419 (7) | 0.0584 (9) | 0.0648 (9) | 0.0079 (6) | 0.0128 (7) | 0.0126 (7) |
C14 | 0.0428 (7) | 0.0613 (9) | 0.0526 (8) | 0.0011 (6) | 0.0072 (6) | 0.0093 (7) |
C15 | 0.0497 (8) | 0.0583 (9) | 0.0690 (10) | 0.0128 (7) | 0.0031 (7) | −0.0057 (8) |
C16 | 0.0335 (16) | 0.0568 (18) | 0.0359 (16) | 0.0064 (13) | 0.0043 (13) | 0.0058 (15) |
C17 | 0.0651 (17) | 0.0577 (15) | 0.066 (2) | 0.0233 (12) | 0.0285 (15) | 0.0263 (13) |
C18 | 0.067 (2) | 0.120 (3) | 0.0395 (17) | 0.0413 (19) | 0.0073 (14) | 0.0339 (15) |
C19 | 0.0474 (16) | 0.101 (3) | 0.0364 (15) | 0.0109 (13) | −0.0047 (12) | 0.0060 (16) |
C20 | 0.0510 (13) | 0.0657 (17) | 0.0532 (14) | 0.0004 (12) | 0.0072 (11) | 0.0093 (14) |
C21 | 0.0532 (15) | 0.0553 (15) | 0.0381 (12) | 0.0048 (12) | 0.0026 (10) | 0.0095 (11) |
C16' | 0.079 (9) | 0.039 (5) | 0.090 (9) | 0.022 (5) | 0.048 (8) | 0.016 (6) |
C17' | 0.070 (6) | 0.128 (8) | 0.077 (8) | 0.016 (5) | 0.031 (5) | 0.059 (6) |
C18' | 0.129 (11) | 0.200 (15) | 0.068 (7) | 0.066 (9) | 0.033 (7) | 0.043 (8) |
C19' | 0.082 (9) | 0.138 (15) | 0.099 (9) | 0.037 (9) | 0.005 (6) | 0.005 (8) |
C20' | 0.059 (5) | 0.047 (4) | 0.063 (6) | −0.014 (4) | 0.009 (4) | 0.005 (5) |
C21' | 0.054 (5) | 0.079 (6) | 0.036 (4) | 0.022 (4) | 0.009 (3) | 0.035 (4) |
C22 | 0.0719 (10) | 0.0747 (10) | 0.0727 (10) | 0.0287 (9) | 0.0265 (9) | 0.0073 (9) |
O1—C1 | 1.3625 (15) | C15—C16' | 1.4946 |
O1—C2 | 1.3587 (16) | C15—C16 | 1.5036 |
N1—N2 | 1.3966 (17) | C15—H15A | 0.9600 |
N1—C2 | 1.2909 (17) | C15—H15B | 0.9600 |
N2—C1 | 1.2903 (18) | C15—H15C | 0.9600 |
O2—C11 | 1.3605 (16) | C15—H15D | 0.9601 |
O2—C15 | 1.4298 (16) | C16—C17 | 1.3900 |
O3—C12 | 1.3543 (16) | C16—C21 | 1.3900 |
O3—C22 | 1.4251 (17) | C17—C18 | 1.3900 |
C1—C3 | 1.452 (2) | C17—H17A | 0.9300 |
C2—C9 | 1.4521 (19) | C18—C19 | 1.3900 |
C3—C4 | 1.375 (2) | C18—H18A | 0.9300 |
C3—C8 | 1.3925 (19) | C19—C20 | 1.3900 |
C4—C5 | 1.383 (2) | C19—H19A | 0.9300 |
C4—H4 | 0.9300 | C20—C21 | 1.3900 |
C5—C6 | 1.375 (2) | C20—H20A | 0.9300 |
C5—H5 | 0.9300 | C21—H21A | 0.9300 |
C6—C7 | 1.366 (3) | C16'—C17' | 1.3900 |
C6—H6 | 0.9300 | C16'—C21' | 1.3900 |
C7—C8 | 1.367 (2) | C17'—C18' | 1.3900 |
C7—H7 | 0.9300 | C17'—H17B | 0.9300 |
C8—H8 | 0.9300 | C18'—C19' | 1.3900 |
C9—C14 | 1.3806 (19) | C18'—H18B | 0.9300 |
C9—C10 | 1.3957 (18) | C19'—C20' | 1.3900 |
C10—C11 | 1.3761 (18) | C19'—H19B | 0.9300 |
C10—H10 | 0.9300 | C20'—C21' | 1.3900 |
C11—C12 | 1.4071 (19) | C20'—H20B | 0.9300 |
C12—C13 | 1.3792 (19) | C21'—H21B | 0.9300 |
C13—C14 | 1.380 (2) | C22—H22A | 0.9600 |
C13—H13 | 0.9300 | C22—H22B | 0.9600 |
C14—H14 | 0.9300 | C22—H22C | 0.9600 |
C2—O1—C1 | 103.08 (10) | C16—C15—H15B | 109.4 |
C2—N1—N2 | 106.43 (12) | H15A—C15—H15B | 108.5 |
C1—N2—N1 | 106.62 (11) | O2—C15—H15C | 110.2 |
C11—O2—C15 | 116.46 (10) | C16'—C15—H15C | 110.2 |
C12—O3—C22 | 117.21 (11) | C16—C15—H15C | 117.7 |
N2—C1—O1 | 111.82 (12) | H15B—C15—H15C | 101.3 |
N2—C1—C3 | 128.78 (12) | O2—C15—H15D | 109.3 |
O1—C1—C3 | 119.37 (12) | C16'—C15—H15D | 109.2 |
N1—C2—O1 | 112.04 (12) | C16—C15—H15D | 102.6 |
N1—C2—C9 | 128.36 (13) | H15A—C15—H15D | 115.1 |
O1—C2—C9 | 119.59 (11) | H15C—C15—H15D | 108.3 |
C4—C3—C8 | 118.93 (15) | C17—C16—C21 | 120.0 |
C4—C3—C1 | 121.47 (13) | C17—C16—C15 | 120.95 (11) |
C8—C3—C1 | 119.59 (14) | C21—C16—C15 | 118.98 (11) |
C3—C4—C5 | 120.33 (15) | C18—C17—C16 | 120.0 |
C3—C4—H4 | 119.8 | C18—C17—H17A | 120.0 |
C5—C4—H4 | 119.8 | C16—C17—H17A | 120.0 |
C6—C5—C4 | 119.83 (17) | C17—C18—C19 | 120.0 |
C6—C5—H5 | 120.1 | C17—C18—H18A | 120.0 |
C4—C5—H5 | 120.1 | C19—C18—H18A | 120.0 |
C7—C6—C5 | 120.21 (17) | C20—C19—C18 | 120.0 |
C7—C6—H6 | 119.9 | C20—C19—H19A | 120.0 |
C5—C6—H6 | 119.9 | C18—C19—H19A | 120.0 |
C6—C7—C8 | 120.29 (16) | C19—C20—C21 | 120.0 |
C6—C7—H7 | 119.9 | C19—C20—H20A | 120.0 |
C8—C7—H7 | 119.9 | C21—C20—H20A | 120.0 |
C7—C8—C3 | 120.42 (16) | C20—C21—C16 | 120.0 |
C7—C8—H8 | 119.8 | C20—C21—H21A | 120.0 |
C3—C8—H8 | 119.8 | C16—C21—H21A | 120.0 |
C14—C9—C10 | 119.56 (13) | C17'—C16'—C21' | 120.0 |
C14—C9—C2 | 119.07 (12) | C17'—C16'—C15 | 119.84 (11) |
C10—C9—C2 | 121.34 (13) | C21'—C16'—C15 | 119.40 (11) |
C11—C10—C9 | 120.29 (13) | C18'—C17'—C16' | 120.0 |
C11—C10—H10 | 119.9 | C18'—C17'—H17B | 120.0 |
C9—C10—H10 | 119.9 | C16'—C17'—H17B | 120.0 |
O2—C11—C10 | 125.19 (12) | C17'—C18'—C19' | 120.0 |
O2—C11—C12 | 115.08 (11) | C17'—C18'—H18B | 120.0 |
C10—C11—C12 | 119.72 (12) | C19'—C18'—H18B | 120.0 |
O3—C12—C13 | 124.81 (13) | C20'—C19'—C18' | 120.0 |
O3—C12—C11 | 115.68 (12) | C20'—C19'—H19B | 120.0 |
C13—C12—C11 | 119.51 (12) | C18'—C19'—H19B | 120.0 |
C12—C13—C14 | 120.41 (13) | C19'—C20'—C21' | 120.0 |
C12—C13—H13 | 119.8 | C19'—C20'—H20B | 120.0 |
C14—C13—H13 | 119.8 | C21'—C20'—H20B | 120.0 |
C13—C14—C9 | 120.47 (13) | C20'—C21'—C16' | 120.0 |
C13—C14—H14 | 119.8 | C20'—C21'—H21B | 120.0 |
C9—C14—H14 | 119.8 | C16'—C21'—H21B | 120.0 |
O2—C15—C16' | 109.49 (10) | O3—C22—H22A | 109.5 |
O2—C15—C16 | 108.27 (10) | O3—C22—H22B | 109.5 |
O2—C15—H15A | 110.5 | H22A—C22—H22B | 109.5 |
C16'—C15—H15A | 102.9 | O3—C22—H22C | 109.5 |
C16—C15—H15A | 110.5 | H22A—C22—H22C | 109.5 |
O2—C15—H15B | 109.6 | H22B—C22—H22C | 109.5 |
C16'—C15—H15B | 115.7 | ||
C2—N1—N2—C1 | 0.25 (16) | C10—C11—C12—O3 | −177.57 (11) |
N1—N2—C1—O1 | −0.17 (16) | O2—C11—C12—C13 | −178.70 (12) |
N1—N2—C1—C3 | −178.21 (13) | C10—C11—C12—C13 | 1.9 (2) |
C2—O1—C1—N2 | 0.03 (14) | O3—C12—C13—C14 | 178.55 (12) |
C2—O1—C1—C3 | 178.27 (11) | C11—C12—C13—C14 | −0.8 (2) |
N2—N1—C2—O1 | −0.24 (16) | C12—C13—C14—C9 | −0.8 (2) |
N2—N1—C2—C9 | 178.35 (13) | C10—C9—C14—C13 | 1.4 (2) |
C1—O1—C2—N1 | 0.14 (14) | C2—C9—C14—C13 | −176.87 (12) |
C1—O1—C2—C9 | −178.59 (11) | C11—O2—C15—C16' | −172.17 (13) |
N2—C1—C3—C4 | 172.68 (14) | C11—O2—C15—C16 | −163.60 (13) |
O1—C1—C3—C4 | −5.2 (2) | O2—C15—C16—C17 | −122.97 (11) |
N2—C1—C3—C8 | −6.0 (2) | C16'—C15—C16—C17 | −23.05 (8) |
O1—C1—C3—C8 | 176.07 (12) | O2—C15—C16—C21 | 60.13 (16) |
C8—C3—C4—C5 | 0.8 (2) | C16'—C15—C16—C21 | 160.05 (5) |
C1—C3—C4—C5 | −177.86 (13) | C21—C16—C17—C18 | 0.0 |
C3—C4—C5—C6 | −0.3 (2) | C15—C16—C17—C18 | −176.87 (13) |
C4—C5—C6—C7 | −0.4 (2) | C16—C17—C18—C19 | 0.0 |
C5—C6—C7—C8 | 0.7 (3) | C17—C18—C19—C20 | 0.0 |
C6—C7—C8—C3 | −0.2 (3) | C18—C19—C20—C21 | 0.0 |
C4—C3—C8—C7 | −0.6 (2) | C19—C20—C21—C16 | 0.0 |
C1—C3—C8—C7 | 178.15 (14) | C17—C16—C21—C20 | 0.0 |
N1—C2—C9—C14 | 5.0 (2) | C15—C16—C21—C20 | 176.94 (13) |
O1—C2—C9—C14 | −176.45 (11) | O2—C15—C16'—C17' | −121.54 (11) |
N1—C2—C9—C10 | −173.17 (14) | C16—C15—C16'—C17' | 155.61 (6) |
O1—C2—C9—C10 | 5.34 (19) | O2—C15—C16'—C21' | 68.41 (16) |
C14—C9—C10—C11 | −0.3 (2) | C16—C15—C16'—C21' | −14.44 (7) |
C2—C9—C10—C11 | 177.87 (12) | C21'—C16'—C17'—C18' | 0.0 |
C15—O2—C11—C10 | −6.2 (2) | C15—C16'—C17'—C18' | −169.99 (13) |
C15—O2—C11—C12 | 174.40 (12) | C16'—C17'—C18'—C19' | 0.0 |
C9—C10—C11—O2 | 179.35 (12) | C17'—C18'—C19'—C20' | 0.0 |
C9—C10—C11—C12 | −1.3 (2) | C18'—C19'—C20'—C21' | 0.0 |
C22—O3—C12—C13 | 1.7 (2) | C19'—C20'—C21'—C16' | 0.0 |
C22—O3—C12—C11 | −178.90 (12) | C17'—C16'—C21'—C20' | 0.0 |
O2—C11—C12—O3 | 1.85 (17) | C15—C16'—C21'—C20' | 170.04 (13) |