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The title compound, C23H15Cl2NO3, crystallizes with two independent mol­ecules in the asymmetric unit. The chroman­one moiety consists of a benzene ring fused with a six-membered heterocyclic ring which adopts a sofa conformation. The five-membered spiro­isoxazoline ring is in an envelope conformation. The p-chloro­phenyl rings bridged by the five-membered ring are nearly perpendicular to each other. The chromanone moiety of one mol­ecule packs into the cavity formed by the p-chloro­phenyl rings of a second mol­ecule through the formation of C—H...π interactions. The structure is stabilized by weak C—H...O, C—H...Cl and C—H...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101000920/bm1437sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101000920/bm1437Isup2.hkl
Contains datablock I

CCDC reference: 163937

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SDP Software (Frenz, 1978); data reduction: CAD-4; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1995); software used to prepare material for publication: PARST97 (Nardelli, 1995) and PLATON (Spek, 2000).

3',4'-Di-(p-chlorophenyl)-spiroisoxazoline-[5'.3]-4-chromanone top
Crystal data top
C23H15Cl2NO3Z = 4
Mr = 424.26F(000) = 872
Triclinic, P1Dx = 1.409 Mg m3
a = 9.764 (3) ÅCu Kα radiation, λ = 1.5418 Å
b = 11.006 (2) ÅCell parameters from 25 reflections
c = 19.780 (3) Åθ = 14–25°
α = 97.56 (2)°µ = 3.13 mm1
β = 102.29 (2)°T = 293 K
γ = 101.73 (2)°Rectangular prism, colourless
V = 1999.4 (8) Å30.35 × 0.10 × 0.05 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
3326 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
Graphite monochromatorθmax = 69.9°, θmin = 2.3°
ω–2θ scansh = 1111
Absorption correction: ψ scan
(North et al., 1968)
k = 013
Tmin = 0.830, Tmax = 0.997l = 2423
7848 measured reflections3 standard reflections every 120min min
7458 independent reflections intensity decay: <1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.139 w = 1/[σ2(Fo2) + (0.0476P)2 + 0.478P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
7458 reflectionsΔρmax = 0.23 e Å3
524 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00118 (14)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl1A0.19206 (14)0.21393 (10)0.31580 (6)0.0694 (4)
Cl2A0.31344 (15)0.82541 (10)0.66336 (6)0.0766 (4)
O1'A0.4091 (3)0.1923 (3)0.73024 (15)0.0558 (8)
N2'A0.4017 (4)0.1656 (3)0.65695 (19)0.0550 (9)
C3'A0.2974 (4)0.2050 (4)0.6235 (2)0.0451 (10)
C4'A0.2174 (4)0.2683 (3)0.6698 (2)0.0437 (10)
H4'A0.11390.22880.65370.052*
C5'A0.2787 (4)0.2313 (4)0.7393 (2)0.0423 (10)
O1A0.3827 (3)0.2895 (3)0.86692 (14)0.0602 (8)
O2A0.0942 (3)0.0391 (2)0.70194 (15)0.0627 (9)
C2A0.3175 (5)0.3312 (4)0.8047 (2)0.0519 (11)
H2A10.38380.40470.79820.062*
H2A20.23090.35630.81130.062*
C3A0.1829 (4)0.1101 (4)0.7510 (2)0.0437 (10)
C4A0.1577 (5)0.0312 (4)0.8380 (2)0.0564 (12)
H4A0.09200.09230.80250.068*
C5A0.1938 (5)0.0568 (5)0.9037 (3)0.0686 (14)
H5A0.15310.13520.91280.082*
C6A0.2905 (6)0.0326 (5)0.9573 (3)0.0721 (14)
H6A0.31480.01471.00240.086*
C7A0.3507 (5)0.1481 (4)0.9437 (2)0.0662 (13)
H7A0.41590.20860.97970.079*
C8A0.3142 (4)0.1746 (4)0.8765 (2)0.0483 (10)
C9A0.2172 (4)0.0850 (4)0.8226 (2)0.0437 (10)
C10A0.2694 (4)0.1977 (4)0.5467 (2)0.0456 (10)
C11A0.1325 (5)0.1876 (4)0.5064 (2)0.0662 (13)
H11A0.05580.18040.52770.079*
C12A0.1068 (5)0.1877 (4)0.4349 (2)0.0674 (13)
H12A0.01340.17880.40830.081*
C13A0.2192 (5)0.2010 (4)0.4040 (2)0.0526 (11)
C14A0.3554 (5)0.2080 (5)0.4422 (2)0.0744 (15)
H14A0.43150.21440.42040.089*
C15A0.3797 (5)0.2056 (5)0.5134 (2)0.0738 (15)
H15A0.47250.20930.53920.089*
C16A0.2425 (4)0.4088 (4)0.66796 (19)0.0414 (10)
C17A0.1289 (5)0.4656 (4)0.65532 (19)0.0462 (10)
H17A0.03550.41660.64740.055*
C18A0.1488 (5)0.5926 (4)0.6540 (2)0.0538 (11)
H18A0.07020.62890.64550.065*
C19A0.2871 (6)0.6648 (4)0.6657 (2)0.0529 (11)
C20A0.4024 (5)0.6118 (4)0.6781 (2)0.0584 (12)
H20A0.49550.66140.68590.070*
C21A0.3806 (5)0.4840 (4)0.6790 (2)0.0579 (12)
H21A0.45950.44800.68710.069*
Cl1B0.10022 (15)0.41962 (11)0.81339 (6)0.0782 (4)
Cl2B0.40011 (14)0.34687 (10)1.12655 (7)0.0738 (4)
O1'B0.0588 (3)0.2450 (2)1.21665 (13)0.0477 (7)
N2'B0.0175 (4)0.2964 (3)1.14330 (16)0.0451 (8)
C3'B0.1279 (4)0.2714 (3)1.1179 (2)0.0408 (9)
C4'B0.2631 (4)0.1922 (3)1.17037 (18)0.0391 (9)
H4'B0.34500.22971.16770.047*
C5'B0.2172 (4)0.2102 (3)1.23847 (19)0.0397 (9)
O1B0.2177 (3)0.1178 (3)1.35861 (14)0.0577 (8)
O2B0.2883 (3)0.4067 (2)1.22831 (14)0.0568 (8)
C2B0.2642 (5)0.0951 (4)1.2964 (2)0.0503 (11)
H2B10.36870.06751.30840.060*
H2B20.22560.02741.27910.060*
C3B0.2570 (4)0.3248 (3)1.2657 (2)0.0417 (10)
C4B0.2650 (5)0.4379 (4)1.3669 (2)0.0559 (12)
H4B0.28030.50681.33940.067*
C5B0.2555 (5)0.4440 (5)1.4346 (3)0.0710 (14)
H5B0.26350.51671.45280.085*
C6B0.2339 (5)0.3410 (5)1.4756 (2)0.0735 (15)
H6B0.22520.34601.52110.088*
C7B0.2249 (5)0.2315 (5)1.4505 (2)0.0635 (13)
H7B0.21370.16201.47910.076*
C8B0.2329 (4)0.2264 (4)1.3815 (2)0.0484 (10)
C9B0.2522 (4)0.3297 (4)1.3388 (2)0.0421 (10)
C10B0.1182 (4)0.3127 (3)1.04350 (19)0.0401 (9)
C15B0.0119 (5)0.3446 (3)0.9931 (2)0.0481 (11)
H15B0.09640.34001.00680.058*
C14B0.0187 (5)0.3829 (3)0.9230 (2)0.0494 (11)
H14B0.10720.40580.88990.059*
C13B0.1052 (5)0.3869 (4)0.9025 (2)0.0515 (11)
C12B0.2360 (5)0.3595 (4)0.9504 (2)0.0632 (13)
H12B0.31930.36560.93590.076*
C11B0.2422 (5)0.3220 (4)1.0217 (2)0.0552 (11)
H11B0.33040.30321.05480.066*
C16B0.2960 (4)0.0579 (3)1.15761 (19)0.0400 (9)
C17B0.4358 (4)0.0095 (4)1.1690 (2)0.0479 (10)
H17B0.51050.02921.18360.057*
C18B0.4693 (5)0.1328 (4)1.1594 (2)0.0553 (12)
H18B0.56500.17621.16680.066*
C19B0.3599 (5)0.1906 (4)1.1389 (2)0.0506 (11)
C20B0.2193 (5)0.1265 (4)1.1270 (2)0.0578 (12)
H20B0.14540.16631.11290.069*
C21B0.1874 (5)0.0032 (4)1.1359 (2)0.0512 (11)
H21B0.09130.04021.12720.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0918 (10)0.0552 (7)0.0494 (7)0.0054 (6)0.0072 (6)0.0043 (5)
Cl2A0.1072 (11)0.0466 (7)0.0689 (8)0.0173 (7)0.0060 (7)0.0129 (6)
O1'A0.0431 (18)0.071 (2)0.0545 (18)0.0135 (15)0.0109 (14)0.0180 (15)
N2'A0.052 (2)0.063 (2)0.057 (2)0.0234 (19)0.0168 (19)0.0176 (19)
C3'A0.041 (3)0.040 (2)0.052 (3)0.011 (2)0.008 (2)0.0058 (19)
C4'A0.037 (2)0.046 (2)0.046 (2)0.008 (2)0.0058 (19)0.0096 (19)
C5'A0.032 (2)0.044 (2)0.050 (2)0.0054 (19)0.0107 (19)0.0093 (19)
O1A0.067 (2)0.0500 (18)0.0473 (17)0.0094 (15)0.0009 (15)0.0108 (14)
O2A0.062 (2)0.0456 (17)0.0632 (19)0.0045 (15)0.0015 (17)0.0028 (15)
C2A0.056 (3)0.044 (2)0.051 (3)0.001 (2)0.013 (2)0.009 (2)
C3A0.036 (3)0.037 (2)0.057 (3)0.0086 (19)0.011 (2)0.005 (2)
C4A0.050 (3)0.051 (3)0.067 (3)0.004 (2)0.016 (2)0.019 (2)
C5A0.076 (4)0.059 (3)0.077 (4)0.014 (3)0.024 (3)0.030 (3)
C6A0.096 (4)0.071 (3)0.058 (3)0.018 (3)0.029 (3)0.031 (3)
C7A0.077 (4)0.070 (3)0.047 (3)0.008 (3)0.015 (2)0.009 (2)
C8A0.050 (3)0.046 (2)0.050 (3)0.007 (2)0.017 (2)0.012 (2)
C9A0.041 (3)0.044 (2)0.049 (2)0.010 (2)0.015 (2)0.013 (2)
C10A0.041 (3)0.045 (2)0.048 (2)0.012 (2)0.007 (2)0.0037 (19)
C11A0.048 (3)0.089 (4)0.060 (3)0.017 (3)0.011 (2)0.008 (3)
C12A0.054 (3)0.087 (4)0.056 (3)0.017 (3)0.005 (3)0.010 (3)
C13A0.067 (3)0.040 (2)0.043 (2)0.009 (2)0.007 (2)0.0013 (19)
C14A0.057 (3)0.109 (4)0.056 (3)0.013 (3)0.021 (3)0.010 (3)
C15A0.045 (3)0.116 (4)0.057 (3)0.017 (3)0.010 (3)0.013 (3)
C16A0.045 (3)0.043 (2)0.038 (2)0.012 (2)0.0118 (19)0.0115 (18)
C17A0.046 (3)0.052 (3)0.043 (2)0.017 (2)0.011 (2)0.012 (2)
C18A0.062 (3)0.056 (3)0.051 (3)0.028 (3)0.014 (2)0.014 (2)
C19A0.080 (4)0.045 (2)0.036 (2)0.017 (3)0.014 (2)0.0109 (19)
C20A0.055 (3)0.053 (3)0.070 (3)0.008 (2)0.018 (2)0.025 (2)
C21A0.049 (3)0.057 (3)0.075 (3)0.014 (2)0.019 (2)0.026 (2)
Cl1B0.1185 (12)0.0726 (8)0.0443 (6)0.0201 (8)0.0267 (7)0.0072 (6)
Cl2B0.0774 (9)0.0436 (6)0.0982 (10)0.0068 (6)0.0205 (7)0.0196 (6)
O1'B0.0425 (18)0.0564 (17)0.0431 (16)0.0139 (14)0.0117 (13)0.0005 (13)
N2'B0.044 (2)0.049 (2)0.0384 (19)0.0089 (17)0.0079 (16)0.0035 (16)
C3'B0.044 (3)0.033 (2)0.044 (2)0.0097 (19)0.007 (2)0.0081 (18)
C4'B0.042 (2)0.038 (2)0.039 (2)0.0115 (19)0.0113 (19)0.0096 (17)
C5'B0.036 (2)0.040 (2)0.042 (2)0.0124 (19)0.0048 (19)0.0067 (18)
O1B0.073 (2)0.0537 (18)0.0479 (17)0.0221 (16)0.0176 (16)0.0007 (14)
O2B0.073 (2)0.0447 (17)0.0583 (18)0.0227 (16)0.0205 (16)0.0076 (14)
C2B0.062 (3)0.044 (2)0.045 (2)0.014 (2)0.014 (2)0.003 (2)
C3B0.040 (2)0.035 (2)0.046 (2)0.0048 (19)0.0094 (19)0.0021 (18)
C4B0.061 (3)0.055 (3)0.050 (3)0.009 (2)0.012 (2)0.013 (2)
C5B0.073 (4)0.075 (4)0.067 (3)0.010 (3)0.017 (3)0.029 (3)
C6B0.067 (4)0.100 (4)0.046 (3)0.001 (3)0.014 (3)0.021 (3)
C7B0.058 (3)0.079 (3)0.047 (3)0.008 (3)0.012 (2)0.004 (3)
C8B0.039 (3)0.057 (3)0.041 (2)0.002 (2)0.004 (2)0.003 (2)
C9B0.036 (2)0.044 (2)0.044 (2)0.0074 (19)0.0087 (19)0.0073 (19)
C10B0.044 (3)0.035 (2)0.040 (2)0.0069 (19)0.009 (2)0.0073 (17)
C15B0.054 (3)0.041 (2)0.045 (2)0.007 (2)0.007 (2)0.0056 (19)
C14B0.057 (3)0.040 (2)0.043 (2)0.009 (2)0.000 (2)0.0062 (19)
C13B0.074 (3)0.039 (2)0.040 (2)0.011 (2)0.014 (2)0.0079 (19)
C12B0.067 (4)0.072 (3)0.053 (3)0.017 (3)0.024 (3)0.004 (2)
C11B0.050 (3)0.065 (3)0.047 (3)0.014 (2)0.009 (2)0.002 (2)
C16B0.042 (3)0.037 (2)0.042 (2)0.0103 (19)0.0117 (19)0.0060 (18)
C17B0.044 (3)0.040 (2)0.057 (3)0.011 (2)0.004 (2)0.009 (2)
C18B0.049 (3)0.045 (3)0.065 (3)0.004 (2)0.008 (2)0.007 (2)
C19B0.062 (3)0.035 (2)0.054 (3)0.008 (2)0.017 (2)0.0081 (19)
C20B0.057 (3)0.045 (3)0.080 (3)0.021 (2)0.017 (3)0.023 (2)
C21B0.039 (3)0.043 (2)0.072 (3)0.011 (2)0.013 (2)0.015 (2)
Geometric parameters (Å, º) top
Cl1A—C13A1.737 (4)Cl1B—C13B1.741 (4)
Cl2A—C19A1.742 (4)Cl2B—C19B1.746 (4)
O1'A—N2'A1.424 (4)O1'B—N2'B1.425 (4)
O1'A—C5'A1.462 (4)O1'B—C5'B1.468 (4)
N2'A—C3'A1.277 (5)N2'B—C3'B1.279 (5)
C3'A—C10A1.473 (5)C3'B—C10B1.459 (5)
C3'A—C4'A1.514 (5)C3'B—C4'B1.514 (5)
C4'A—C5'A1.520 (5)C4'B—C16B1.513 (5)
C4'A—C16A1.522 (5)C4'B—C5'B1.531 (5)
C5'A—C2A1.508 (5)C5'B—C2B1.512 (5)
C5'A—C3A1.540 (5)C5'B—C3B1.524 (5)
O1A—C8A1.361 (4)O1B—C8B1.357 (5)
O1A—C2A1.437 (4)O1B—C2B1.434 (4)
O2A—C3A1.212 (4)O2B—C3B1.219 (4)
C3A—C9A1.461 (5)C3B—C9B1.463 (5)
C4A—C5A1.354 (6)C4B—C5B1.370 (6)
C4A—C9A1.394 (5)C4B—C9B1.396 (5)
C5A—C6A1.381 (6)C5B—C6B1.385 (6)
C6A—C7A1.374 (6)C6B—C7B1.374 (6)
C7A—C8A1.387 (5)C7B—C8B1.390 (5)
C8A—C9A1.386 (5)C8B—C9B1.395 (5)
C10A—C15A1.372 (6)C10B—C15B1.386 (5)
C10A—C11A1.377 (5)C10B—C11B1.387 (5)
C11A—C12A1.382 (6)C15B—C14B1.378 (5)
C12A—C13A1.358 (6)C14B—C13B1.362 (5)
C13A—C14A1.365 (6)C13B—C12B1.369 (6)
C14A—C15A1.383 (6)C12B—C11B1.400 (5)
C16A—C17A1.374 (5)C16B—C17B1.371 (5)
C16A—C21A1.387 (5)C16B—C21B1.391 (5)
C17A—C18A1.376 (5)C17B—C18B1.378 (5)
C18A—C19A1.376 (6)C18B—C19B1.367 (5)
C19A—C20A1.362 (6)C19B—C20B1.365 (6)
C20A—C21A1.382 (5)C20B—C21B1.373 (5)
N2'A—O1'A—C5'A108.6 (3)N2'B—O1'B—C5'B107.8 (3)
C3'A—N2'A—O1'A108.7 (3)C3'B—N2'B—O1'B108.9 (3)
N2'A—C3'A—C10A121.0 (4)N2'B—C3'B—C10B121.3 (4)
N2'A—C3'A—C4'A114.5 (4)N2'B—C3'B—C4'B114.4 (3)
C10A—C3'A—C4'A124.3 (4)C10B—C3'B—C4'B124.3 (4)
C3'A—C4'A—C5'A99.9 (3)C16B—C4'B—C3'B111.1 (3)
C3'A—C4'A—C16A111.0 (3)C16B—C4'B—C5'B115.9 (3)
C5'A—C4'A—C16A117.0 (3)C3'B—C4'B—C5'B98.9 (3)
O1'A—C5'A—C2A108.8 (3)O1'B—C5'B—C2B108.5 (3)
O1'A—C5'A—C4'A104.7 (3)O1'B—C5'B—C3B104.2 (3)
C2A—C5'A—C4'A117.3 (3)C2B—C5'B—C3B111.1 (3)
O1'A—C5'A—C3A103.2 (3)O1'B—C5'B—C4'B104.1 (3)
C2A—C5'A—C3A109.6 (3)C2B—C5'B—C4'B115.7 (3)
C4'A—C5'A—C3A112.2 (3)C3B—C5'B—C4'B112.2 (3)
C8A—O1A—C2A115.9 (3)C8B—O1B—C2B117.5 (3)
O1A—C2A—C5'A113.0 (3)O1B—C2B—C5'B113.1 (3)
O2A—C3A—C9A124.5 (4)O2B—C3B—C9B123.1 (4)
O2A—C3A—C5'A120.5 (4)O2B—C3B—C5'B121.6 (3)
C9A—C3A—C5'A114.7 (3)C9B—C3B—C5'B115.2 (3)
C5A—C4A—C9A121.2 (4)C5B—C4B—C9B120.9 (4)
C4A—C5A—C6A120.4 (4)C4B—C5B—C6B119.4 (5)
C7A—C6A—C5A119.6 (4)C7B—C6B—C5B121.4 (5)
C6A—C7A—C8A120.1 (5)C6B—C7B—C8B118.9 (5)
O1A—C8A—C9A123.2 (4)O1B—C8B—C7B116.4 (4)
O1A—C8A—C7A116.4 (4)O1B—C8B—C9B122.8 (4)
C9A—C8A—C7A120.4 (4)C7B—C8B—C9B120.7 (4)
C8A—C9A—C4A118.2 (4)C8B—C9B—C4B118.6 (4)
C8A—C9A—C3A120.8 (4)C8B—C9B—C3B120.5 (4)
C4A—C9A—C3A120.9 (4)C4B—C9B—C3B121.0 (4)
C15A—C10A—C11A117.8 (4)C15B—C10B—C11B118.1 (4)
C15A—C10A—C3'A121.0 (4)C15B—C10B—C3'B122.2 (4)
C11A—C10A—C3'A121.1 (4)C11B—C10B—C3'B119.7 (4)
C10A—C11A—C12A121.4 (5)C14B—C15B—C10B121.3 (4)
C13A—C12A—C11A119.4 (4)C13B—C14B—C15B119.4 (4)
C12A—C13A—C14A120.5 (4)C14B—C13B—C12B121.5 (4)
C12A—C13A—Cl1A120.4 (4)C14B—C13B—Cl1B119.8 (4)
C14A—C13A—Cl1A119.1 (4)C12B—C13B—Cl1B118.6 (4)
C13A—C14A—C15A119.6 (4)C13B—C12B—C11B118.8 (4)
C10A—C15A—C14A121.2 (4)C10B—C11B—C12B120.8 (4)
C17A—C16A—C21A117.7 (4)C17B—C16B—C21B117.3 (4)
C17A—C16A—C4'A121.1 (4)C17B—C16B—C4'B120.7 (3)
C21A—C16A—C4'A121.3 (4)C21B—C16B—C4'B122.0 (4)
C16A—C17A—C18A122.2 (4)C16B—C17B—C18B122.0 (4)
C19A—C18A—C17A118.7 (4)C19B—C18B—C17B119.1 (4)
C20A—C19A—C18A120.7 (4)C20B—C19B—C18B120.6 (4)
C20A—C19A—Cl2A120.1 (4)C20B—C19B—Cl2B119.6 (3)
C18A—C19A—Cl2A119.1 (4)C18B—C19B—Cl2B119.8 (4)
C19A—C20A—C21A119.8 (4)C19B—C20B—C21B119.8 (4)
C20A—C21A—C16A120.8 (4)C20B—C21B—C16B121.2 (4)
C5'A—O1'A—N2'A—C3'A11.3 (4)C5'B—O1'B—N2'B—C3'B13.5 (4)
O1'A—N2'A—C3'A—C10A175.9 (3)O1'B—N2'B—C3'B—C10B179.9 (3)
O1'A—N2'A—C3'A—C4'A1.1 (5)O1'B—N2'B—C3'B—C4'B2.7 (4)
N2'A—C3'A—C4'A—C5'A12.1 (4)N2'B—C3'B—C4'B—C16B105.8 (4)
C10A—C3'A—C4'A—C5'A173.3 (4)C10B—C3'B—C4'B—C16B71.4 (4)
N2'A—C3'A—C4'A—C16A112.0 (4)N2'B—C3'B—C4'B—C5'B16.5 (4)
C10A—C3'A—C4'A—C16A62.7 (5)C10B—C3'B—C4'B—C5'B166.2 (3)
N2'A—O1'A—C5'A—C2A144.6 (3)N2'B—O1'B—C5'B—C2B147.0 (3)
N2'A—O1'A—C5'A—C4'A18.4 (4)N2'B—O1'B—C5'B—C3B94.5 (3)
N2'A—O1'A—C5'A—C3A99.1 (3)N2'B—O1'B—C5'B—C4'B23.3 (3)
C3'A—C4'A—C5'A—O1'A17.4 (4)C16B—C4'B—C5'B—O1'B96.2 (4)
C16A—C4'A—C5'A—O1'A102.4 (4)C3'B—C4'B—C5'B—O1'B22.6 (3)
C3'A—C4'A—C5'A—C2A138.0 (3)C16B—C4'B—C5'B—C2B22.8 (5)
C16A—C4'A—C5'A—C2A18.2 (5)C3'B—C4'B—C5'B—C2B141.6 (3)
C3'A—C4'A—C5'A—C3A93.8 (4)C16B—C4'B—C5'B—C3B151.8 (3)
C16A—C4'A—C5'A—C3A146.4 (3)C3'B—C4'B—C5'B—C3B89.5 (3)
C8A—O1A—C2A—C5'A47.6 (5)C8B—O1B—C2B—C5'B44.2 (5)
O1'A—C5'A—C2A—O1A57.8 (4)O1'B—C5'B—C2B—O1B63.3 (4)
C4'A—C5'A—C2A—O1A176.4 (3)C3B—C5'B—C2B—O1B50.7 (5)
C3A—C5'A—C2A—O1A54.3 (4)C4'B—C5'B—C2B—O1B179.8 (3)
O1'A—C5'A—C3A—O2A94.1 (4)O1'B—C5'B—C3B—O2B95.5 (4)
C2A—C5'A—C3A—O2A150.2 (4)C2B—C5'B—C3B—O2B147.8 (4)
C4'A—C5'A—C3A—O2A18.1 (5)C4'B—C5'B—C3B—O2B16.5 (5)
O1'A—C5'A—C3A—C9A81.0 (4)O1'B—C5'B—C3B—C9B83.5 (4)
C2A—C5'A—C3A—C9A34.8 (4)C2B—C5'B—C3B—C9B33.3 (5)
C4'A—C5'A—C3A—C9A166.9 (3)C4'B—C5'B—C3B—C9B164.5 (3)
C9A—C4A—C5A—C6A0.3 (7)C9B—C4B—C5B—C6B0.5 (7)
C4A—C5A—C6A—C7A0.2 (8)C4B—C5B—C6B—C7B1.5 (8)
C5A—C6A—C7A—C8A0.1 (7)C5B—C6B—C7B—C8B2.3 (7)
C2A—O1A—C8A—C9A19.5 (6)C2B—O1B—C8B—C7B163.1 (4)
C2A—O1A—C8A—C7A163.0 (4)C2B—O1B—C8B—C9B18.3 (5)
C6A—C7A—C8A—O1A177.7 (4)C6B—C7B—C8B—O1B177.5 (4)
C6A—C7A—C8A—C9A0.1 (7)C6B—C7B—C8B—C9B1.1 (7)
O1A—C8A—C9A—C4A177.6 (4)O1B—C8B—C9B—C4B179.3 (4)
C7A—C8A—C9A—C4A0.2 (6)C7B—C8B—C9B—C4B0.7 (6)
O1A—C8A—C9A—C3A0.1 (6)O1B—C8B—C9B—C3B0.0 (6)
C7A—C8A—C9A—C3A177.3 (4)C7B—C8B—C9B—C3B178.5 (4)
C5A—C4A—C9A—C8A0.3 (6)C5B—C4B—C9B—C8B1.5 (6)
C5A—C4A—C9A—C3A177.2 (4)C5B—C4B—C9B—C3B177.7 (4)
O2A—C3A—C9A—C8A176.2 (4)O2B—C3B—C9B—C8B172.2 (4)
C5'A—C3A—C9A—C8A9.0 (5)C5'B—C3B—C9B—C8B8.8 (5)
O2A—C3A—C9A—C4A6.3 (6)O2B—C3B—C9B—C4B8.5 (6)
C5'A—C3A—C9A—C4A168.5 (4)C5'B—C3B—C9B—C4B170.4 (4)
N2'A—C3'A—C10A—C15A30.3 (6)N2'B—C3'B—C10B—C15B20.4 (6)
C4'A—C3'A—C10A—C15A144.0 (4)C4'B—C3'B—C10B—C15B156.7 (4)
N2'A—C3'A—C10A—C11A152.2 (4)N2'B—C3'B—C10B—C11B158.9 (4)
C4'A—C3'A—C10A—C11A33.6 (6)C4'B—C3'B—C10B—C11B24.0 (5)
C15A—C10A—C11A—C12A1.3 (7)C11B—C10B—C15B—C14B0.9 (6)
C3'A—C10A—C11A—C12A176.4 (4)C3'B—C10B—C15B—C14B179.8 (3)
C10A—C11A—C12A—C13A1.5 (7)C10B—C15B—C14B—C13B1.5 (6)
C11A—C12A—C13A—C14A3.2 (7)C15B—C14B—C13B—C12B3.1 (6)
C11A—C12A—C13A—Cl1A175.0 (4)C15B—C14B—C13B—Cl1B173.5 (3)
C12A—C13A—C14A—C15A2.1 (7)C14B—C13B—C12B—C11B2.4 (7)
Cl1A—C13A—C14A—C15A176.1 (4)Cl1B—C13B—C12B—C11B174.3 (3)
C11A—C10A—C15A—C14A2.4 (7)C15B—C10B—C11B—C12B1.6 (6)
C3'A—C10A—C15A—C14A175.3 (4)C3'B—C10B—C11B—C12B179.0 (4)
C13A—C14A—C15A—C10A0.8 (8)C13B—C12B—C11B—C10B0.0 (7)
C3'A—C4'A—C16A—C17A129.9 (4)C3'B—C4'B—C16B—C17B145.3 (4)
C5'A—C4'A—C16A—C17A116.5 (4)C5'B—C4'B—C16B—C17B102.8 (4)
C3'A—C4'A—C16A—C21A50.2 (5)C3'B—C4'B—C16B—C21B36.4 (5)
C5'A—C4'A—C16A—C21A63.5 (5)C5'B—C4'B—C16B—C21B75.4 (5)
C21A—C16A—C17A—C18A0.6 (6)C21B—C16B—C17B—C18B0.1 (6)
C4'A—C16A—C17A—C18A179.4 (4)C4'B—C16B—C17B—C18B178.5 (4)
C16A—C17A—C18A—C19A0.1 (6)C16B—C17B—C18B—C19B1.0 (6)
C17A—C18A—C19A—C20A0.2 (6)C17B—C18B—C19B—C20B1.0 (6)
C17A—C18A—C19A—Cl2A179.4 (3)C17B—C18B—C19B—Cl2B179.9 (3)
C18A—C19A—C20A—C21A0.0 (7)C18B—C19B—C20B—C21B0.2 (7)
Cl2A—C19A—C20A—C21A179.2 (3)Cl2B—C19B—C20B—C21B179.3 (3)
C19A—C20A—C21A—C16A0.5 (7)C19B—C20B—C21B—C16B0.7 (7)
C17A—C16A—C21A—C20A0.7 (6)C17B—C16B—C21B—C20B0.7 (6)
C4'A—C16A—C21A—C20A179.2 (4)C4'B—C16B—C21B—C20B177.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4A—H4A···O2A0.982.402.780 (5)103
C2B—H2B2···Cl1Ai0.972.763.600 (4)145
C5A—H5A···Cg20.932.853.740 (5)160
C6A—H6A···Cg30.932.833.671 (5)151
C17A—H17A···Cg1ii0.932.633.515 (5)159
C15A—H15A···Cg1iii0.932.743.578 (5)151
Symmetry codes: (i) x, y, z+1; (ii) x, y, z+2; (iii) x+1, y, z+2.
Table 1. Cremer and Pople conformational parameters for the rings in the two molecules top
RingMoleculeq2Åq3ÅQTÅφ2°Conformation
Ring BI0.335 (4)0.271 (4)0.431 (4)-39.7 (6)sofa
Ring BII0.312 (4)-0.252 (4)0.401 (4)141.0 (7)sofa
Ring CI0.183 (4)140.8 (11)envelope
Ring CII0.237 (4)-41.5 (8)envelope
 

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