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
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.058
- wR factor = 0.178
- Data-to-parameter ratio = 17.5
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.00 PLAT038_ALERT_1_A _diffrn_measured_fraction_theta_max Not Given . ? PLAT039_ALERT_1_A _diffrn_measured_fraction_theta_full Not Given . ?
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.73 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C27 - C28 = 5.52 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C12 PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... C1G H20 C1G PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... C1G C20 C1G PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... C1G C20 H20 C1G
3 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
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. |