Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805035294/fl6199sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805035294/fl6199Isup2.hkl |
CCDC reference: 293894
Data collection: SMART (Bruker, 2003); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.
C20H25N2O2+·C4H6ClO2− | Dx = 1.291 Mg m−3 |
Mr = 446.96 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P43212 | Cell parameters from 1003 reflections |
Hall symbol: P 4nw 2abw | θ = 2.0–25.5° |
a = 10.5135 (5) Å | µ = 0.20 mm−1 |
c = 41.618 (3) Å | T = 299 K |
V = 4600.2 (5) Å3 | Columnar, colorless |
Z = 8 | 0.38 × 0.38 × 0.33 mm |
F(000) = 1904 |
Bruker SMART APEX CCD area-detector diffractometer | 4091 independent reflections |
Radiation source: fine-focus sealed tube | 3651 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 25.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −12→12 |
Tmin = 0.835, Tmax = 0.937 | k = −12→12 |
32606 measured reflections | l = −45→49 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0337P)2 + 2.0903P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.009 |
4091 reflections | Δρmax = 0.30 e Å−3 |
290 parameters | Δρmin = −0.31 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 1587 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (11) |
Experimental. Owing to the long c axes, the detector was positioned 10 cm from the crystal in order to differentiate reflections. The data-collection strategy used two different detector positions to achieve acceptable 2θ coverage (Table 2). |
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 | ||
Cl1 | 0.69383 (13) | 1.07381 (10) | 0.02488 (2) | 0.1044 (4) | |
O3 | 0.53144 (19) | 1.1160 (2) | 0.10077 (5) | 0.0563 (5) | |
O4 | 0.7296 (2) | 1.1820 (2) | 0.09458 (5) | 0.0732 (7) | |
C1 | 0.6392 (3) | 1.1123 (3) | 0.08781 (6) | 0.0456 (7) | |
C2 | 0.6598 (3) | 1.0051 (3) | 0.06335 (6) | 0.0459 (7) | |
H2 | 0.5806 | 0.9564 | 0.0616 | 0.055* | |
C3 | 0.7636 (3) | 0.9159 (4) | 0.07356 (10) | 0.0795 (11) | |
H3A | 0.7462 | 0.8877 | 0.0953 | 0.095* | |
H3B | 0.8433 | 0.9623 | 0.0740 | 0.095* | |
C4 | 0.7800 (4) | 0.7990 (4) | 0.05224 (11) | 0.1083 (16) | |
H4A | 0.7001 | 0.7555 | 0.0503 | 0.162* | |
H4B | 0.8418 | 0.7430 | 0.0616 | 0.162* | |
H4C | 0.8085 | 0.8250 | 0.0313 | 0.162* | |
O2 | 0.30341 (19) | 0.14784 (18) | 0.06762 (5) | 0.0449 (5) | |
N1 | 0.0779 (2) | 0.33565 (19) | 0.08616 (5) | 0.0382 (5) | |
C5 | 0.0938 (2) | −0.0728 (2) | 0.11316 (6) | 0.0399 (6) | |
O1 | −0.0254 (2) | −0.0165 (2) | 0.19548 (5) | 0.0626 (6) | |
C6 | 0.0795 (2) | 0.1997 (2) | 0.07447 (6) | 0.0344 (6) | |
H6 | 0.0029 | 0.1583 | 0.0828 | 0.041* | |
C7 | 0.1920 (3) | 0.4094 (2) | 0.07524 (6) | 0.0432 (6) | |
H7A | 0.2681 | 0.3760 | 0.0854 | 0.052* | |
H7B | 0.1831 | 0.4980 | 0.0813 | 0.052* | |
C8 | 0.2033 (2) | 0.3978 (3) | 0.03854 (6) | 0.0450 (7) | |
H8A | 0.2181 | 0.4809 | 0.0291 | 0.054* | |
H8B | 0.2742 | 0.3430 | 0.0330 | 0.054* | |
C9 | −0.0417 (3) | 0.3986 (3) | 0.07425 (6) | 0.0448 (7) | |
H9A | −0.0547 | 0.4782 | 0.0856 | 0.054* | |
H9B | −0.1142 | 0.3440 | 0.0784 | 0.054* | |
C10 | 0.0639 (2) | −0.0073 (3) | 0.14197 (6) | 0.0431 (6) | |
H10 | 0.0867 | 0.0777 | 0.1443 | 0.052* | |
N2 | 0.0860 (3) | −0.2748 (2) | 0.08354 (7) | 0.0586 (7) | |
C11 | 0.0669 (3) | 0.2039 (2) | 0.03739 (6) | 0.0400 (6) | |
H11A | 0.1329 | 0.1520 | 0.0277 | 0.048* | |
H11B | −0.0149 | 0.1696 | 0.0310 | 0.048* | |
C12 | 0.0571 (3) | −0.2027 (3) | 0.10997 (7) | 0.0484 (7) | |
C13 | 0.1600 (2) | −0.0166 (2) | 0.08693 (6) | 0.0375 (6) | |
C14 | 0.1948 (2) | 0.1240 (2) | 0.08703 (6) | 0.0365 (6) | |
H14 | 0.2131 | 0.1505 | 0.1091 | 0.044* | |
C15 | −0.0308 (2) | 0.4241 (2) | 0.03788 (6) | 0.0415 (6) | |
H15 | −0.0074 | 0.5136 | 0.0349 | 0.050* | |
C16 | 0.1880 (3) | −0.0912 (3) | 0.06103 (7) | 0.0499 (7) | |
H16 | 0.2329 | −0.0574 | 0.0438 | 0.060* | |
C17 | 0.0016 (3) | −0.0685 (3) | 0.16623 (7) | 0.0506 (7) | |
C18 | −0.1536 (3) | 0.4011 (3) | 0.02069 (7) | 0.0546 (8) | |
H18 | −0.1907 | 0.3212 | 0.0227 | 0.066* | |
C19 | −0.0101 (3) | −0.2607 (3) | 0.13533 (8) | 0.0632 (9) | |
H19 | −0.0361 | −0.3448 | 0.1334 | 0.076* | |
C20 | 0.0225 (3) | 0.1082 (3) | 0.20172 (7) | 0.0592 (8) | |
H20A | 0.1119 | 0.1107 | 0.1971 | 0.089* | |
H20B | 0.0089 | 0.1292 | 0.2239 | 0.089* | |
H20C | −0.0212 | 0.1685 | 0.1884 | 0.089* | |
C21 | 0.1491 (3) | −0.2187 (3) | 0.06039 (8) | 0.0583 (8) | |
H21 | 0.1695 | −0.2667 | 0.0423 | 0.070* | |
C22 | 0.0792 (2) | 0.3416 (2) | 0.02558 (6) | 0.0391 (6) | |
H22 | 0.0804 | 0.3430 | 0.0020 | 0.047* | |
C23 | −0.0372 (3) | −0.1956 (3) | 0.16240 (9) | 0.0636 (9) | |
H23 | −0.0822 | −0.2353 | 0.1788 | 0.076* | |
C24 | −0.2116 (3) | 0.4845 (4) | 0.00323 (8) | 0.0799 (11) | |
H24A | −0.1771 | 0.5653 | 0.0007 | 0.096* | |
H24B | −0.2879 | 0.4637 | −0.0068 | 0.096* | |
H99A | 0.074 (3) | 0.333 (2) | 0.1089 (7) | 0.051 (8)* | |
H99B | 0.369 (4) | 0.121 (4) | 0.0768 (9) | 0.102 (15)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1768 (12) | 0.0905 (7) | 0.0458 (5) | −0.0561 (8) | 0.0082 (6) | −0.0032 (5) |
O3 | 0.0525 (13) | 0.0727 (15) | 0.0437 (11) | 0.0087 (11) | 0.0019 (10) | −0.0031 (10) |
O4 | 0.0710 (15) | 0.0687 (15) | 0.0799 (16) | −0.0203 (13) | 0.0007 (12) | −0.0290 (12) |
C1 | 0.0495 (17) | 0.0475 (17) | 0.0397 (15) | 0.0013 (15) | −0.0055 (14) | 0.0026 (13) |
C2 | 0.0457 (16) | 0.0479 (17) | 0.0441 (16) | −0.0088 (13) | 0.0000 (12) | −0.0023 (13) |
C3 | 0.064 (2) | 0.076 (2) | 0.099 (3) | 0.0089 (19) | −0.021 (2) | −0.027 (2) |
C4 | 0.077 (3) | 0.100 (3) | 0.148 (4) | 0.030 (3) | −0.021 (3) | −0.055 (3) |
O2 | 0.0372 (11) | 0.0473 (11) | 0.0503 (11) | 0.0007 (9) | 0.0036 (9) | 0.0098 (9) |
N1 | 0.0486 (14) | 0.0329 (12) | 0.0331 (12) | 0.0000 (10) | 0.0021 (10) | −0.0012 (9) |
C5 | 0.0384 (14) | 0.0321 (14) | 0.0491 (15) | 0.0043 (12) | −0.0037 (12) | 0.0069 (12) |
O1 | 0.0683 (14) | 0.0623 (14) | 0.0572 (13) | 0.0088 (12) | 0.0216 (11) | 0.0146 (11) |
C6 | 0.0378 (14) | 0.0270 (12) | 0.0383 (13) | −0.0027 (11) | 0.0054 (11) | −0.0023 (10) |
C7 | 0.0495 (16) | 0.0320 (14) | 0.0480 (15) | −0.0092 (13) | −0.0048 (13) | 0.0001 (12) |
C8 | 0.0404 (15) | 0.0488 (17) | 0.0458 (16) | −0.0032 (13) | 0.0012 (12) | 0.0112 (13) |
C9 | 0.0456 (16) | 0.0343 (14) | 0.0544 (17) | 0.0056 (12) | 0.0082 (13) | 0.0000 (12) |
C10 | 0.0433 (15) | 0.0366 (15) | 0.0495 (16) | 0.0047 (12) | 0.0058 (13) | 0.0113 (12) |
N2 | 0.0712 (18) | 0.0332 (13) | 0.0712 (17) | 0.0023 (13) | −0.0076 (15) | −0.0011 (13) |
C11 | 0.0421 (15) | 0.0388 (15) | 0.0390 (14) | 0.0028 (12) | −0.0021 (12) | −0.0059 (12) |
C12 | 0.0478 (17) | 0.0327 (15) | 0.0648 (19) | 0.0008 (13) | −0.0069 (15) | 0.0089 (14) |
C13 | 0.0384 (14) | 0.0319 (14) | 0.0423 (15) | 0.0044 (11) | −0.0029 (12) | 0.0027 (12) |
C14 | 0.0396 (14) | 0.0356 (14) | 0.0343 (13) | −0.0027 (12) | 0.0031 (11) | −0.0008 (11) |
C15 | 0.0414 (15) | 0.0335 (14) | 0.0495 (15) | −0.0005 (12) | −0.0003 (12) | 0.0048 (12) |
C16 | 0.0569 (18) | 0.0415 (16) | 0.0513 (17) | 0.0051 (13) | 0.0028 (14) | −0.0020 (13) |
C17 | 0.0454 (17) | 0.0512 (18) | 0.0553 (18) | 0.0122 (14) | 0.0086 (14) | 0.0156 (15) |
C18 | 0.0415 (17) | 0.0551 (19) | 0.0671 (19) | −0.0002 (15) | −0.0024 (15) | 0.0022 (16) |
C19 | 0.066 (2) | 0.0380 (17) | 0.086 (2) | −0.0112 (15) | 0.0030 (19) | 0.0146 (17) |
C20 | 0.0496 (18) | 0.074 (2) | 0.0539 (18) | 0.0013 (17) | 0.0054 (15) | −0.0001 (16) |
C21 | 0.075 (2) | 0.0415 (17) | 0.0581 (19) | 0.0096 (16) | −0.0054 (17) | −0.0108 (15) |
C22 | 0.0386 (14) | 0.0429 (15) | 0.0359 (13) | −0.0012 (12) | −0.0028 (12) | 0.0031 (12) |
C23 | 0.062 (2) | 0.0496 (19) | 0.079 (2) | −0.0015 (16) | 0.0160 (17) | 0.0237 (18) |
C24 | 0.055 (2) | 0.113 (3) | 0.071 (2) | −0.002 (2) | −0.0103 (18) | 0.030 (2) |
Cl1—C2 | 1.793 (3) | C9—C15 | 1.541 (4) |
O3—C1 | 1.256 (3) | C9—H9A | 0.9700 |
O4—C1 | 1.232 (3) | C9—H9B | 0.9700 |
C1—C2 | 1.534 (4) | C10—C17 | 1.365 (4) |
C2—C3 | 1.501 (4) | C10—H10 | 0.9300 |
C2—H2 | 0.9800 | N2—C21 | 1.310 (4) |
C3—C4 | 1.525 (5) | N2—C12 | 1.370 (4) |
C3—H3A | 0.9700 | C11—C22 | 1.534 (4) |
C3—H3B | 0.9700 | C11—H11A | 0.9700 |
C4—H4A | 0.9600 | C11—H11B | 0.9700 |
C4—H4B | 0.9600 | C12—C19 | 1.409 (4) |
C4—H4C | 0.9600 | C13—C16 | 1.365 (4) |
O2—C14 | 1.421 (3) | C13—C14 | 1.522 (3) |
O2—H99B | 0.84 (4) | C14—H14 | 0.9800 |
N1—C7 | 1.499 (3) | C15—C18 | 1.496 (4) |
N1—C9 | 1.505 (3) | C15—C22 | 1.534 (4) |
N1—C6 | 1.510 (3) | C15—H15 | 0.9800 |
N1—H99A | 0.95 (3) | C16—C21 | 1.402 (4) |
C5—C10 | 1.418 (4) | C16—H16 | 0.9300 |
C5—C13 | 1.423 (4) | C17—C23 | 1.405 (4) |
C5—C12 | 1.425 (4) | C18—C24 | 1.292 (4) |
O1—C17 | 1.364 (3) | C18—H18 | 0.9300 |
O1—C20 | 1.428 (4) | C19—C23 | 1.349 (4) |
C6—C14 | 1.542 (4) | C19—H19 | 0.9300 |
C6—C11 | 1.550 (3) | C20—H20A | 0.9600 |
C6—H6 | 0.9800 | C20—H20B | 0.9600 |
C7—C8 | 1.537 (4) | C20—H20C | 0.9600 |
C7—H7A | 0.9700 | C21—H21 | 0.9300 |
C7—H7B | 0.9700 | C22—H22 | 0.9800 |
C8—C22 | 1.530 (3) | C23—H23 | 0.9300 |
C8—H8A | 0.9700 | C24—H24A | 0.9300 |
C8—H8B | 0.9700 | C24—H24B | 0.9300 |
O4—C1—O3 | 125.4 (3) | C21—N2—C12 | 117.0 (2) |
O4—C1—C2 | 118.7 (3) | C22—C11—C6 | 109.8 (2) |
O3—C1—C2 | 115.8 (3) | C22—C11—H11A | 109.7 |
C3—C2—C1 | 112.0 (2) | C6—C11—H11A | 109.7 |
C3—C2—Cl1 | 111.1 (2) | C22—C11—H11B | 109.7 |
C1—C2—Cl1 | 108.9 (2) | C6—C11—H11B | 109.7 |
C3—C2—H2 | 108.2 | H11A—C11—H11B | 108.2 |
C1—C2—H2 | 108.2 | N2—C12—C19 | 118.3 (3) |
Cl1—C2—H2 | 108.2 | N2—C12—C5 | 123.0 (3) |
C2—C3—C4 | 114.9 (3) | C19—C12—C5 | 118.7 (3) |
C2—C3—H3A | 108.5 | C16—C13—C5 | 118.2 (2) |
C4—C3—H3A | 108.5 | C16—C13—C14 | 120.5 (2) |
C2—C3—H3B | 108.5 | C5—C13—C14 | 121.2 (2) |
C4—C3—H3B | 108.5 | O2—C14—C13 | 111.3 (2) |
H3A—C3—H3B | 107.5 | O2—C14—C6 | 110.4 (2) |
C3—C4—H4A | 109.5 | C13—C14—C6 | 108.1 (2) |
C3—C4—H4B | 109.5 | O2—C14—H14 | 109.0 |
H4A—C4—H4B | 109.5 | C13—C14—H14 | 109.0 |
C3—C4—H4C | 109.5 | C6—C14—H14 | 109.0 |
H4A—C4—H4C | 109.5 | C18—C15—C22 | 113.5 (2) |
H4B—C4—H4C | 109.5 | C18—C15—C9 | 112.2 (2) |
C14—O2—H99B | 110 (3) | C22—C15—C9 | 106.6 (2) |
C7—N1—C9 | 109.97 (19) | C18—C15—H15 | 108.1 |
C7—N1—C6 | 112.5 (2) | C22—C15—H15 | 108.1 |
C9—N1—C6 | 108.65 (19) | C9—C15—H15 | 108.1 |
C7—N1—H99A | 110.4 (17) | C13—C16—C21 | 120.1 (3) |
C9—N1—H99A | 107.8 (17) | C13—C16—H16 | 119.9 |
C6—N1—H99A | 107.4 (16) | C21—C16—H16 | 119.9 |
C10—C5—C13 | 123.7 (2) | O1—C17—C10 | 124.8 (3) |
C10—C5—C12 | 119.0 (2) | O1—C17—C23 | 114.9 (3) |
C13—C5—C12 | 117.3 (2) | C10—C17—C23 | 120.2 (3) |
C17—O1—C20 | 117.2 (2) | C24—C18—C15 | 124.5 (3) |
N1—C6—C14 | 112.9 (2) | C24—C18—H18 | 117.7 |
N1—C6—C11 | 107.0 (2) | C15—C18—H18 | 117.7 |
C14—C6—C11 | 114.8 (2) | C23—C19—C12 | 120.8 (3) |
N1—C6—H6 | 107.3 | C23—C19—H19 | 119.6 |
C14—C6—H6 | 107.3 | C12—C19—H19 | 119.6 |
C11—C6—H6 | 107.3 | O1—C20—H20A | 109.5 |
N1—C7—C8 | 108.8 (2) | O1—C20—H20B | 109.5 |
N1—C7—H7A | 109.9 | H20A—C20—H20B | 109.5 |
C8—C7—H7A | 109.9 | O1—C20—H20C | 109.5 |
N1—C7—H7B | 109.9 | H20A—C20—H20C | 109.5 |
C8—C7—H7B | 109.9 | H20B—C20—H20C | 109.5 |
H7A—C7—H7B | 108.3 | N2—C21—C16 | 124.4 (3) |
C22—C8—C7 | 108.4 (2) | N2—C21—H21 | 117.8 |
C22—C8—H8A | 110.0 | C16—C21—H21 | 117.8 |
C7—C8—H8A | 110.0 | C8—C22—C15 | 107.9 (2) |
C22—C8—H8B | 110.0 | C8—C22—C11 | 108.8 (2) |
C7—C8—H8B | 110.0 | C15—C22—C11 | 111.3 (2) |
H8A—C8—H8B | 108.4 | C8—C22—H22 | 109.6 |
N1—C9—C15 | 109.7 (2) | C15—C22—H22 | 109.6 |
N1—C9—H9A | 109.7 | C11—C22—H22 | 109.6 |
C15—C9—H9A | 109.7 | C19—C23—C17 | 121.0 (3) |
N1—C9—H9B | 109.7 | C19—C23—H23 | 119.5 |
C15—C9—H9B | 109.7 | C17—C23—H23 | 119.5 |
H9A—C9—H9B | 108.2 | C18—C24—H24A | 120.0 |
C17—C10—C5 | 120.2 (3) | C18—C24—H24B | 120.0 |
C17—C10—H10 | 119.9 | H24A—C24—H24B | 120.0 |
C5—C10—H10 | 119.9 | ||
O4—C1—C2—C3 | 57.8 (4) | C16—C13—C14—C6 | 92.8 (3) |
O3—C1—C2—C3 | −118.0 (3) | C5—C13—C14—C6 | −84.9 (3) |
O4—C1—C2—Cl1 | −65.4 (3) | N1—C6—C14—O2 | −82.7 (3) |
O3—C1—C2—Cl1 | 118.8 (2) | C11—C6—C14—O2 | 40.4 (3) |
C1—C2—C3—C4 | 173.8 (3) | N1—C6—C14—C13 | 155.4 (2) |
Cl1—C2—C3—C4 | −64.2 (4) | C11—C6—C14—C13 | −81.6 (3) |
C7—N1—C6—C14 | 61.3 (3) | N1—C9—C15—C18 | 141.3 (2) |
C9—N1—C6—C14 | −176.7 (2) | N1—C9—C15—C22 | 16.4 (3) |
C7—N1—C6—C11 | −65.9 (3) | C5—C13—C16—C21 | 1.5 (4) |
C9—N1—C6—C11 | 56.1 (3) | C14—C13—C16—C21 | −176.3 (3) |
C9—N1—C7—C8 | −67.7 (3) | C20—O1—C17—C10 | −4.2 (4) |
C6—N1—C7—C8 | 53.6 (3) | C20—O1—C17—C23 | 174.3 (3) |
N1—C7—C8—C22 | 12.7 (3) | C5—C10—C17—O1 | 176.2 (2) |
C7—N1—C9—C15 | 50.5 (3) | C5—C10—C17—C23 | −2.2 (4) |
C6—N1—C9—C15 | −73.0 (3) | C22—C15—C18—C24 | −115.6 (3) |
C13—C5—C10—C17 | −179.1 (2) | C9—C15—C18—C24 | 123.5 (3) |
C12—C5—C10—C17 | 0.4 (4) | N2—C12—C19—C23 | 177.7 (3) |
N1—C6—C11—C22 | 9.1 (3) | C5—C12—C19—C23 | −1.3 (5) |
C14—C6—C11—C22 | −117.0 (2) | C12—N2—C21—C16 | −0.2 (5) |
C21—N2—C12—C19 | −179.6 (3) | C13—C16—C21—N2 | −0.2 (5) |
C21—N2—C12—C5 | −0.7 (4) | C7—C8—C22—C15 | 54.0 (3) |
C10—C5—C12—N2 | −177.6 (3) | C7—C8—C22—C11 | −66.9 (3) |
C13—C5—C12—N2 | 2.0 (4) | C18—C15—C22—C8 | 165.4 (2) |
C10—C5—C12—C19 | 1.3 (4) | C9—C15—C22—C8 | −70.6 (2) |
C13—C5—C12—C19 | −179.2 (3) | C18—C15—C22—C11 | −75.3 (3) |
C10—C5—C13—C16 | 177.2 (2) | C9—C15—C22—C11 | 48.7 (3) |
C12—C5—C13—C16 | −2.3 (4) | C6—C11—C22—C8 | 54.1 (3) |
C10—C5—C13—C14 | −4.9 (4) | C6—C11—C22—C15 | −64.6 (3) |
C12—C5—C13—C14 | 175.6 (2) | C12—C19—C23—C17 | −0.5 (5) |
C16—C13—C14—O2 | −28.5 (3) | O1—C17—C23—C19 | −176.3 (3) |
C5—C13—C14—O2 | 153.7 (2) | C10—C17—C23—C19 | 2.3 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H99B···O3i | 0.84 (4) | 1.98 (4) | 2.786 (3) | 162 (4) |
N1—H99A···O4ii | 0.95 (3) | 2.54 (3) | 3.299 (3) | 137 (2) |
N1—H99A···O3ii | 0.95 (3) | 1.82 (3) | 2.718 (3) | 158 (2) |
Symmetry codes: (i) x, y−1, z; (ii) x−1/2, −y+3/2, −z+1/4. |