1-(2-Chlorophenyl)-1H-indan-2-spiro-2′-pyrrolizidine-3′-spiro-3′′-1H-indole-1,3,2′′(2H,3′′H)-trione
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803027284/na6271sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803027284/na6271Isup2.hkl |
CCDC reference: 232146
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: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
C28H21ClN2O3 | F(000) = 976 |
Mr = 468.92 | Dx = 1.335 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.8456 (6) Å | Cell parameters from 4187 reflections |
b = 14.1502 (8) Å | θ = 2.3–24.3° |
c = 15.2068 (9) Å | µ = 0.20 mm−1 |
β = 92.053 (1)° | T = 293 K |
V = 2332.3 (2) Å3 | Needle, pale yellow |
Z = 4 | 0.18 × 0.17 × 0.11 mm |
CCD Area-Detector diffractometer | 3882 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 28.0°, θmin = 2.0° |
ω scans | h = −8→14 |
14407 measured reflections | k = −18→18 |
5387 independent reflections | l = −20→19 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.178 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.1051P)2 + 0.4748P] where P = (Fo2 + 2Fc2)/3 |
5387 reflections | (Δ/σ)max < 0.001 |
307 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
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 | 0.89248 (9) | 0.26176 (7) | 0.23346 (4) | 0.0873 (3) | |
N1 | 0.96749 (15) | 0.04470 (11) | −0.09583 (11) | 0.0405 (4) | |
H1 | 1.0153 | −0.0023 | −0.0836 | 0.049* | |
C2 | 0.87356 (18) | 0.04233 (14) | −0.16038 (12) | 0.0386 (4) | |
C3 | 0.8439 (2) | −0.03019 (16) | −0.21754 (16) | 0.0542 (6) | |
H3 | 0.8857 | −0.0875 | −0.2143 | 0.065* | |
C4 | 0.7506 (3) | −0.0155 (2) | −0.27946 (17) | 0.0663 (7) | |
H4 | 0.7280 | −0.0638 | −0.3182 | 0.080* | |
C5 | 0.6902 (3) | 0.0703 (2) | −0.28482 (17) | 0.0700 (8) | |
H5 | 0.6281 | 0.0791 | −0.3278 | 0.084* | |
C6 | 0.7203 (2) | 0.14431 (18) | −0.22687 (14) | 0.0538 (6) | |
H6 | 0.6798 | 0.2021 | −0.2312 | 0.065* | |
C7 | 0.81188 (18) | 0.12893 (14) | −0.16327 (12) | 0.0366 (4) | |
C8 | 0.86601 (16) | 0.19233 (12) | −0.09169 (11) | 0.0304 (4) | |
C9 | 0.97533 (17) | 0.12900 (13) | −0.05445 (12) | 0.0345 (4) | |
N10 | 0.90408 (15) | 0.28545 (11) | −0.12009 (10) | 0.0362 (4) | |
C11 | 1.0168 (2) | 0.29181 (16) | −0.17087 (15) | 0.0516 (6) | |
H11A | 0.9966 | 0.3055 | −0.2322 | 0.062* | |
H11B | 1.0628 | 0.2331 | −0.1673 | 0.062* | |
C12 | 1.0904 (3) | 0.3715 (2) | −0.1292 (2) | 0.0729 (8) | |
H12A | 1.0716 | 0.4309 | −0.1585 | 0.087* | |
H12B | 1.1782 | 0.3594 | −0.1321 | 0.087* | |
C13 | 1.0516 (2) | 0.37424 (16) | −0.03428 (16) | 0.0518 (6) | |
H13A | 1.0641 | 0.4365 | −0.0087 | 0.062* | |
H13B | 1.0964 | 0.3279 | 0.0014 | 0.062* | |
C14 | 0.91467 (18) | 0.34979 (13) | −0.04376 (13) | 0.0367 (4) | |
H14 | 0.8678 | 0.4076 | −0.0571 | 0.044* | |
C15 | 0.85482 (17) | 0.29784 (13) | 0.03223 (12) | 0.0354 (4) | |
H15 | 0.9213 | 0.2673 | 0.0671 | 0.042* | |
C16 | 0.77902 (16) | 0.21750 (12) | −0.01571 (11) | 0.0305 (4) | |
C17 | 0.74705 (17) | 0.13477 (13) | 0.04472 (12) | 0.0349 (4) | |
C18 | 0.61276 (18) | 0.12913 (14) | 0.05038 (13) | 0.0406 (4) | |
C19 | 0.5439 (2) | 0.06670 (18) | 0.09995 (16) | 0.0576 (6) | |
H19 | 0.5819 | 0.0229 | 0.1376 | 0.069* | |
C20 | 0.4175 (2) | 0.0725 (2) | 0.0908 (2) | 0.0741 (8) | |
H20 | 0.3690 | 0.0314 | 0.1224 | 0.089* | |
C21 | 0.3613 (2) | 0.1383 (2) | 0.0355 (2) | 0.0765 (9) | |
H21 | 0.2756 | 0.1405 | 0.0310 | 0.092* | |
C22 | 0.4289 (2) | 0.2007 (2) | −0.01337 (18) | 0.0632 (7) | |
H22 | 0.3904 | 0.2450 | −0.0503 | 0.076* | |
C23 | 0.55672 (18) | 0.19480 (15) | −0.00517 (13) | 0.0411 (5) | |
C24 | 0.65008 (17) | 0.25068 (13) | −0.05014 (13) | 0.0359 (4) | |
C25 | 0.78313 (19) | 0.35896 (15) | 0.09480 (14) | 0.0441 (5) | |
C26 | 0.7022 (2) | 0.42896 (17) | 0.06477 (18) | 0.0558 (6) | |
H26 | 0.6912 | 0.4387 | 0.0045 | 0.067* | |
C27 | 0.6371 (3) | 0.4848 (2) | 0.1225 (2) | 0.0756 (9) | |
H27 | 0.5823 | 0.5303 | 0.1007 | 0.091* | |
C28 | 0.6542 (3) | 0.4725 (2) | 0.2115 (2) | 0.0828 (10) | |
H28 | 0.6118 | 0.5106 | 0.2500 | 0.099* | |
C29 | 0.7327 (3) | 0.4048 (2) | 0.24404 (19) | 0.0780 (9) | |
H29 | 0.7439 | 0.3969 | 0.3045 | 0.094* | |
C30 | 0.7963 (2) | 0.34763 (19) | 0.18645 (15) | 0.0593 (7) | |
O31 | 1.05445 (13) | 0.15182 (10) | 0.00005 (10) | 0.0466 (4) | |
O32 | 0.62882 (14) | 0.31223 (11) | −0.10334 (10) | 0.0503 (4) | |
O33 | 0.81984 (14) | 0.08227 (11) | 0.08147 (10) | 0.0511 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1071 (7) | 0.1089 (7) | 0.0450 (4) | −0.0044 (5) | −0.0082 (4) | 0.0067 (4) |
N1 | 0.0375 (9) | 0.0356 (9) | 0.0485 (9) | 0.0067 (7) | 0.0032 (7) | 0.0018 (7) |
C2 | 0.0376 (10) | 0.0400 (10) | 0.0387 (10) | −0.0036 (8) | 0.0094 (8) | −0.0028 (8) |
C3 | 0.0545 (14) | 0.0462 (12) | 0.0624 (14) | −0.0037 (10) | 0.0117 (11) | −0.0185 (11) |
C4 | 0.0678 (16) | 0.0753 (18) | 0.0555 (14) | −0.0068 (14) | −0.0007 (12) | −0.0318 (13) |
C5 | 0.0696 (17) | 0.086 (2) | 0.0526 (14) | 0.0005 (15) | −0.0209 (13) | −0.0215 (13) |
C6 | 0.0561 (14) | 0.0603 (14) | 0.0438 (12) | 0.0059 (11) | −0.0131 (10) | −0.0063 (10) |
C7 | 0.0360 (10) | 0.0402 (10) | 0.0338 (9) | −0.0039 (8) | 0.0020 (7) | −0.0027 (8) |
C8 | 0.0274 (8) | 0.0314 (9) | 0.0324 (8) | −0.0002 (7) | −0.0006 (7) | 0.0012 (7) |
C9 | 0.0302 (9) | 0.0371 (10) | 0.0365 (9) | 0.0011 (7) | 0.0033 (7) | 0.0051 (7) |
N10 | 0.0406 (9) | 0.0311 (8) | 0.0371 (8) | −0.0026 (6) | 0.0037 (7) | 0.0026 (6) |
C11 | 0.0564 (14) | 0.0466 (12) | 0.0531 (13) | −0.0053 (10) | 0.0197 (11) | 0.0021 (10) |
C12 | 0.0605 (16) | 0.0716 (17) | 0.0882 (19) | −0.0242 (13) | 0.0264 (14) | −0.0051 (15) |
C13 | 0.0442 (12) | 0.0422 (12) | 0.0693 (15) | −0.0129 (9) | 0.0046 (11) | −0.0068 (10) |
C14 | 0.0363 (10) | 0.0308 (9) | 0.0431 (10) | −0.0020 (7) | 0.0011 (8) | −0.0011 (8) |
C15 | 0.0317 (9) | 0.0370 (10) | 0.0373 (9) | −0.0027 (7) | −0.0013 (7) | −0.0034 (8) |
C16 | 0.0274 (8) | 0.0308 (9) | 0.0332 (9) | 0.0007 (7) | −0.0009 (7) | 0.0008 (7) |
C17 | 0.0345 (9) | 0.0355 (9) | 0.0350 (9) | 0.0010 (7) | 0.0041 (7) | 0.0003 (7) |
C18 | 0.0345 (10) | 0.0439 (11) | 0.0438 (10) | −0.0040 (8) | 0.0063 (8) | −0.0011 (9) |
C19 | 0.0500 (13) | 0.0625 (15) | 0.0612 (14) | −0.0087 (11) | 0.0161 (11) | 0.0086 (12) |
C20 | 0.0469 (14) | 0.095 (2) | 0.0822 (19) | −0.0210 (14) | 0.0205 (13) | 0.0086 (16) |
C21 | 0.0297 (11) | 0.113 (2) | 0.087 (2) | −0.0090 (13) | 0.0101 (12) | 0.0028 (18) |
C22 | 0.0329 (11) | 0.0865 (18) | 0.0700 (16) | 0.0035 (12) | −0.0014 (11) | 0.0037 (14) |
C23 | 0.0298 (9) | 0.0490 (11) | 0.0446 (11) | 0.0000 (8) | 0.0011 (8) | −0.0024 (9) |
C24 | 0.0328 (9) | 0.0364 (10) | 0.0382 (10) | 0.0038 (7) | −0.0022 (8) | −0.0034 (8) |
C25 | 0.0389 (11) | 0.0481 (12) | 0.0458 (11) | −0.0104 (9) | 0.0068 (9) | −0.0132 (9) |
C26 | 0.0466 (12) | 0.0503 (13) | 0.0707 (15) | 0.0007 (10) | 0.0071 (11) | −0.0168 (11) |
C27 | 0.0542 (15) | 0.0594 (16) | 0.115 (3) | −0.0036 (12) | 0.0239 (16) | −0.0284 (16) |
C28 | 0.076 (2) | 0.086 (2) | 0.090 (2) | −0.0213 (17) | 0.0472 (18) | −0.0383 (18) |
C29 | 0.087 (2) | 0.091 (2) | 0.0576 (15) | −0.0349 (18) | 0.0327 (15) | −0.0275 (15) |
C30 | 0.0609 (15) | 0.0685 (16) | 0.0493 (13) | −0.0240 (12) | 0.0123 (11) | −0.0150 (11) |
O31 | 0.0342 (7) | 0.0508 (8) | 0.0540 (8) | 0.0037 (6) | −0.0085 (6) | 0.0006 (7) |
O32 | 0.0450 (8) | 0.0479 (8) | 0.0574 (9) | 0.0091 (7) | −0.0057 (7) | 0.0130 (7) |
O33 | 0.0411 (8) | 0.0553 (9) | 0.0574 (9) | 0.0109 (7) | 0.0077 (7) | 0.0227 (7) |
Cl1—C30 | 1.739 (3) | C14—H14 | 0.9800 |
N1—C9 | 1.350 (2) | C15—C25 | 1.520 (3) |
N1—C2 | 1.390 (3) | C15—C16 | 1.567 (2) |
N1—H1 | 0.8600 | C15—H15 | 0.9800 |
C2—C3 | 1.376 (3) | C16—C17 | 1.536 (3) |
C2—C7 | 1.396 (3) | C16—C24 | 1.548 (2) |
C3—C4 | 1.373 (4) | C17—O33 | 1.207 (2) |
C3—H3 | 0.9300 | C17—C18 | 1.464 (3) |
C4—C5 | 1.381 (4) | C18—C23 | 1.382 (3) |
C4—H4 | 0.9300 | C18—C19 | 1.395 (3) |
C5—C6 | 1.400 (3) | C19—C20 | 1.376 (4) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—C7 | 1.378 (3) | C20—C21 | 1.381 (4) |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C7—C8 | 1.513 (2) | C21—C22 | 1.382 (4) |
C8—N10 | 1.451 (2) | C21—H21 | 0.9300 |
C8—C16 | 1.559 (2) | C22—C23 | 1.390 (3) |
C8—C9 | 1.575 (2) | C22—H22 | 0.9300 |
C9—O31 | 1.215 (2) | C23—C24 | 1.472 (3) |
N10—C11 | 1.472 (3) | C24—O32 | 1.205 (2) |
N10—C14 | 1.476 (2) | C25—C26 | 1.390 (3) |
C11—C12 | 1.508 (3) | C25—C30 | 1.405 (3) |
C11—H11A | 0.9700 | C26—C27 | 1.391 (3) |
C11—H11B | 0.9700 | C26—H26 | 0.9300 |
C12—C13 | 1.518 (4) | C27—C28 | 1.371 (5) |
C12—H12A | 0.9700 | C27—H27 | 0.9300 |
C12—H12B | 0.9700 | C28—C29 | 1.362 (5) |
C13—C14 | 1.527 (3) | C28—H28 | 0.9300 |
C13—H13A | 0.9700 | C29—C30 | 1.393 (4) |
C13—H13B | 0.9700 | C29—H29 | 0.9300 |
C14—C15 | 1.533 (3) | ||
C9—N1—C2 | 112.5 (2) | C15—C14—H14 | 109.0 |
C9—N1—H1 | 123.7 | C25—C15—C14 | 116.03 (16) |
C2—N1—H1 | 123.7 | C25—C15—C16 | 115.61 (15) |
C3—C2—N1 | 127.8 (2) | C14—C15—C16 | 103.08 (14) |
C3—C2—C7 | 122.3 (2) | C25—C15—H15 | 107.2 |
N1—C2—C7 | 109.84 (16) | C14—C15—H15 | 107.2 |
C4—C3—C2 | 118.1 (2) | C16—C15—H15 | 107.2 |
C4—C3—H3 | 121.0 | C17—C16—C24 | 102.29 (14) |
C2—C3—H3 | 121.0 | C17—C16—C8 | 115.15 (14) |
C3—C4—C5 | 120.7 (2) | C24—C16—C8 | 112.45 (14) |
C3—C4—H4 | 119.7 | C17—C16—C15 | 113.61 (14) |
C5—C4—H4 | 119.7 | C24—C16—C15 | 112.93 (14) |
C4—C5—C6 | 121.4 (2) | C8—C16—C15 | 100.91 (13) |
C4—C5—H5 | 119.3 | O33—C17—C18 | 125.09 (18) |
C6—C5—H5 | 119.3 | O33—C17—C16 | 126.06 (17) |
C7—C6—C5 | 118.0 (2) | C18—C17—C16 | 108.85 (15) |
C7—C6—H6 | 121.0 | C23—C18—C19 | 121.59 (19) |
C5—C6—H6 | 121.0 | C23—C18—C17 | 110.12 (17) |
C6—C7—C2 | 119.5 (2) | C19—C18—C17 | 128.2 (2) |
C6—C7—C8 | 131.49 (18) | C20—C19—C18 | 117.2 (2) |
C2—C7—C8 | 108.95 (16) | C20—C19—H19 | 121.4 |
N10—C8—C7 | 115.6 (2) | C18—C19—H19 | 121.4 |
N10—C8—C16 | 101.50 (14) | C19—C20—C21 | 121.3 (2) |
C7—C8—C16 | 116.06 (14) | C19—C20—H20 | 119.4 |
N10—C8—C9 | 113.89 (14) | C21—C20—H20 | 119.4 |
C7—C8—C9 | 100.89 (14) | C20—C21—C22 | 121.8 (2) |
C16—C8—C9 | 109.34 (13) | C20—C21—H21 | 119.1 |
O31—C9—N1 | 125.72 (18) | C22—C21—H21 | 119.1 |
O31—C9—C8 | 126.73 (17) | C21—C22—C23 | 117.4 (2) |
N1—C9—C8 | 107.52 (15) | C21—C22—H22 | 121.3 |
C8—N10—C11 | 117.5 (2) | C23—C22—H22 | 121.3 |
C8—N10—C14 | 109.9 (1) | C18—C23—C22 | 120.7 (2) |
C11—N10—C14 | 109.4 (2) | C18—C23—C24 | 110.50 (17) |
N10—C11—C12 | 105.21 (18) | C22—C23—C24 | 128.8 (2) |
N10—C11—H11A | 110.7 | O32—C24—C23 | 125.56 (18) |
C12—C11—H11A | 110.7 | O32—C24—C16 | 126.49 (17) |
N10—C11—H11B | 110.7 | C23—C24—C16 | 107.94 (15) |
C12—C11—H11B | 110.7 | C26—C25—C30 | 116.6 (2) |
H11A—C11—H11B | 108.8 | C26—C25—C15 | 122.07 (19) |
C11—C12—C13 | 104.98 (19) | C30—C25—C15 | 121.3 (2) |
C11—C12—H12A | 110.8 | C25—C26—C27 | 121.7 (3) |
C13—C12—H12A | 110.8 | C25—C26—H26 | 119.1 |
C11—C12—H12B | 110.8 | C27—C26—H26 | 119.1 |
C13—C12—H12B | 110.8 | C28—C27—C26 | 119.8 (3) |
H12A—C12—H12B | 108.8 | C28—C27—H27 | 120.1 |
C12—C13—C14 | 101.90 (19) | C26—C27—H27 | 120.1 |
C12—C13—H13A | 111.4 | C29—C28—C27 | 120.6 (3) |
C14—C13—H13A | 111.4 | C29—C28—H28 | 119.7 |
C12—C13—H13B | 111.4 | C27—C28—H28 | 119.7 |
C14—C13—H13B | 111.4 | C28—C29—C30 | 119.8 (3) |
H13A—C13—H13B | 109.3 | C28—C29—H29 | 120.1 |
N10—C14—C13 | 105.19 (16) | C30—C29—H29 | 120.1 |
N10—C14—C15 | 105.89 (14) | C29—C30—C25 | 121.5 (3) |
C13—C14—C15 | 118.31 (17) | C29—C30—Cl1 | 116.8 (2) |
N10—C14—H14 | 109.0 | C25—C30—Cl1 | 121.71 (19) |
C13—C14—H14 | 109.0 | ||
C9—N1—C2—C3 | 176.6 (2) | C7—C8—C16—C15 | −168.77 (15) |
C9—N1—C2—C7 | −0.8 (2) | C9—C8—C16—C15 | 77.99 (16) |
N1—C2—C3—C4 | −176.8 (2) | C25—C15—C16—C17 | −72.7 (2) |
C7—C2—C3—C4 | 0.4 (3) | C14—C15—C16—C17 | 159.62 (15) |
C2—C3—C4—C5 | 1.1 (4) | C25—C15—C16—C24 | 43.2 (2) |
C3—C4—C5—C6 | −1.0 (4) | C14—C15—C16—C24 | −84.45 (17) |
C4—C5—C6—C7 | −0.6 (4) | C25—C15—C16—C8 | 163.47 (16) |
C5—C6—C7—C2 | 2.0 (3) | C14—C15—C16—C8 | 35.80 (16) |
C5—C6—C7—C8 | −180.0 (2) | C24—C16—C17—O33 | 174.26 (19) |
C3—C2—C7—C6 | −2.0 (3) | C8—C16—C17—O33 | 52.0 (3) |
N1—C2—C7—C6 | 175.64 (18) | C15—C16—C17—O33 | −63.7 (2) |
C3—C2—C7—C8 | 179.61 (18) | C24—C16—C17—C18 | −5.38 (19) |
N1—C2—C7—C8 | −2.8 (2) | C8—C16—C17—C18 | −127.67 (16) |
C6—C7—C8—N10 | −50.2 (3) | C15—C16—C17—C18 | 116.66 (17) |
C2—C7—C8—N10 | 127.98 (17) | O33—C17—C18—C23 | −175.1 (2) |
C6—C7—C8—C16 | 68.5 (3) | C16—C17—C18—C23 | 4.5 (2) |
C2—C7—C8—C16 | −113.34 (17) | O33—C17—C18—C19 | 2.5 (4) |
C6—C7—C8—C9 | −173.5 (2) | C16—C17—C18—C19 | −177.8 (2) |
C2—C7—C8—C9 | 4.67 (18) | C23—C18—C19—C20 | 0.5 (4) |
C2—N1—C9—O31 | −174.56 (18) | C17—C18—C19—C20 | −176.9 (2) |
C2—N1—C9—C8 | 3.9 (2) | C18—C19—C20—C21 | −0.7 (4) |
N10—C8—C9—O31 | 48.9 (2) | C19—C20—C21—C22 | 0.3 (5) |
C7—C8—C9—O31 | 173.33 (18) | C20—C21—C22—C23 | 0.3 (4) |
C16—C8—C9—O31 | −63.9 (2) | C19—C18—C23—C22 | 0.0 (3) |
N10—C8—C9—N1 | −129.59 (16) | C17—C18—C23—C22 | 177.9 (2) |
C7—C8—C9—N1 | −5.12 (18) | C19—C18—C23—C24 | −179.3 (2) |
C16—C8—C9—N1 | 117.68 (16) | C17—C18—C23—C24 | −1.5 (2) |
C7—C8—N10—C11 | −73.1 (2) | C21—C22—C23—C18 | −0.5 (4) |
C16—C8—N10—C11 | 160.44 (16) | C21—C22—C23—C24 | 178.8 (2) |
C9—C8—N10—C11 | 43.1 (2) | C18—C23—C24—O32 | 178.9 (2) |
C7—C8—N10—C14 | 160.93 (15) | C22—C23—C24—O32 | −0.4 (4) |
C16—C8—N10—C14 | 34.48 (17) | C18—C23—C24—C16 | −2.1 (2) |
C9—C8—N10—C14 | −82.90 (18) | C22—C23—C24—C16 | 178.6 (2) |
C8—N10—C11—C12 | −133.1 (2) | C17—C16—C24—O32 | −176.51 (19) |
C14—N10—C11—C12 | −6.8 (2) | C8—C16—C24—O32 | −52.4 (2) |
N10—C11—C12—C13 | 27.3 (3) | C15—C16—C24—O32 | 61.0 (2) |
C11—C12—C13—C14 | −36.4 (3) | C17—C16—C24—C23 | 4.49 (18) |
C8—N10—C14—C13 | 114.38 (17) | C8—C16—C24—C23 | 128.59 (16) |
C11—N10—C14—C13 | −16.1 (2) | C15—C16—C24—C23 | −118.01 (17) |
C8—N10—C14—C15 | −11.64 (19) | C14—C15—C25—C26 | 44.5 (3) |
C11—N10—C14—C15 | −142.09 (16) | C16—C15—C25—C26 | −76.4 (2) |
C12—C13—C14—N10 | 32.0 (2) | C14—C15—C25—C30 | −135.1 (2) |
C12—C13—C14—C15 | 149.9 (2) | C16—C15—C25—C30 | 104.0 (2) |
N10—C14—C15—C25 | −143.60 (16) | C30—C25—C26—C27 | −0.2 (3) |
C13—C14—C15—C25 | 98.8 (2) | C15—C25—C26—C27 | −179.8 (2) |
N10—C14—C15—C16 | −16.20 (18) | C25—C26—C27—C28 | 1.3 (4) |
C13—C14—C15—C16 | −133.76 (17) | C26—C27—C28—C29 | −1.2 (4) |
N10—C8—C16—C17 | −165.38 (14) | C27—C28—C29—C30 | 0.0 (4) |
C7—C8—C16—C17 | 68.48 (19) | C28—C29—C30—C25 | 1.1 (4) |
C9—C8—C16—C17 | −44.76 (19) | C28—C29—C30—Cl1 | −178.9 (2) |
N10—C8—C16—C24 | 77.97 (16) | C26—C25—C30—C29 | −1.0 (3) |
C7—C8—C16—C24 | −48.2 (2) | C15—C25—C30—C29 | 178.6 (2) |
C9—C8—C16—C24 | −161.41 (14) | C26—C25—C30—Cl1 | 179.03 (17) |
N10—C8—C16—C15 | −42.63 (15) | C15—C25—C30—Cl1 | −1.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O32 | 0.93 | 2.57 | 3.208 (3) | 127 |
C13—H13B···O31 | 0.97 | 2.53 | 3.190 (3) | 125 |
C15—H15···Cl1 | 0.98 | 2.56 | 3.115 (2) | 116 |
C15—H15···O31 | 0.98 | 2.43 | 3.045 (2) | 121 |
C26—H26···O32 | 0.93 | 2.50 | 3.123 (3) | 124 |
N1—H1···O31i | 0.86 | 2.59 | 3.152 (2) | 124 |
N1—H1···O33i | 0.86 | 2.11 | 2.926 (2) | 157 |
C21—H21···O31ii | 0.93 | 2.43 | 3.357 (3) | 173 |
C20—H20···C1giii | 0.93 | 2.59 | 3.508 (4) | 170 |
Symmetry codes: (i) −x+2, −y, −z; (ii) x−1, y, z; (iii) −x+1, −y, −z. |