The title compound, C
23H
15Cl
2NO
3, 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
CCDC reference: 163937
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
C23H15Cl2NO3 | Z = 4 |
Mr = 424.26 | F(000) = 872 |
Triclinic, P1 | Dx = 1.409 Mg m−3 |
a = 9.764 (3) Å | Cu Kα radiation, λ = 1.5418 Å |
b = 11.006 (2) Å | Cell parameters from 25 reflections |
c = 19.780 (3) Å | θ = 14–25° |
α = 97.56 (2)° | µ = 3.13 mm−1 |
β = 102.29 (2)° | T = 293 K |
γ = 101.73 (2)° | Rectangular prism, colourless |
V = 1999.4 (8) Å3 | 0.35 × 0.10 × 0.05 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 3326 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.045 |
Graphite monochromator | θmax = 69.9°, θmin = 2.3° |
ω–2θ scans | h = −11→11 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→13 |
Tmin = 0.830, Tmax = 0.997 | l = −24→23 |
7848 measured reflections | 3 standard reflections every 120min min |
7458 independent reflections | intensity decay: <1% |
Refinement top
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)] = 0.048 | H-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 reflections | Δρmax = 0.23 e Å−3 |
524 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
Cl1A | 0.19206 (14) | 0.21393 (10) | 0.31580 (6) | 0.0694 (4) | |
Cl2A | 0.31344 (15) | 0.82541 (10) | 0.66336 (6) | 0.0766 (4) | |
O1'A | 0.4091 (3) | 0.1923 (3) | 0.73024 (15) | 0.0558 (8) | |
N2'A | 0.4017 (4) | 0.1656 (3) | 0.65695 (19) | 0.0550 (9) | |
C3'A | 0.2974 (4) | 0.2050 (4) | 0.6235 (2) | 0.0451 (10) | |
C4'A | 0.2174 (4) | 0.2683 (3) | 0.6698 (2) | 0.0437 (10) | |
H4'A | 0.1139 | 0.2288 | 0.6537 | 0.052* | |
C5'A | 0.2787 (4) | 0.2313 (4) | 0.7393 (2) | 0.0423 (10) | |
O1A | 0.3827 (3) | 0.2895 (3) | 0.86692 (14) | 0.0602 (8) | |
O2A | 0.0942 (3) | 0.0391 (2) | 0.70194 (15) | 0.0627 (9) | |
C2A | 0.3175 (5) | 0.3312 (4) | 0.8047 (2) | 0.0519 (11) | |
H2A1 | 0.3838 | 0.4047 | 0.7982 | 0.062* | |
H2A2 | 0.2309 | 0.3563 | 0.8113 | 0.062* | |
C3A | 0.1829 (4) | 0.1101 (4) | 0.7510 (2) | 0.0437 (10) | |
C4A | 0.1577 (5) | −0.0312 (4) | 0.8380 (2) | 0.0564 (12) | |
H4A | 0.0920 | −0.0923 | 0.8025 | 0.068* | |
C5A | 0.1938 (5) | −0.0568 (5) | 0.9037 (3) | 0.0686 (14) | |
H5A | 0.1531 | −0.1352 | 0.9128 | 0.082* | |
C6A | 0.2905 (6) | 0.0326 (5) | 0.9573 (3) | 0.0721 (14) | |
H6A | 0.3148 | 0.0147 | 1.0024 | 0.086* | |
C7A | 0.3507 (5) | 0.1481 (4) | 0.9437 (2) | 0.0662 (13) | |
H7A | 0.4159 | 0.2086 | 0.9797 | 0.079* | |
C8A | 0.3142 (4) | 0.1746 (4) | 0.8765 (2) | 0.0483 (10) | |
C9A | 0.2172 (4) | 0.0850 (4) | 0.8226 (2) | 0.0437 (10) | |
C10A | 0.2694 (4) | 0.1977 (4) | 0.5467 (2) | 0.0456 (10) | |
C11A | 0.1325 (5) | 0.1876 (4) | 0.5064 (2) | 0.0662 (13) | |
H11A | 0.0558 | 0.1804 | 0.5277 | 0.079* | |
C12A | 0.1068 (5) | 0.1877 (4) | 0.4349 (2) | 0.0674 (13) | |
H12A | 0.0134 | 0.1788 | 0.4083 | 0.081* | |
C13A | 0.2192 (5) | 0.2010 (4) | 0.4040 (2) | 0.0526 (11) | |
C14A | 0.3554 (5) | 0.2080 (5) | 0.4422 (2) | 0.0744 (15) | |
H14A | 0.4315 | 0.2144 | 0.4204 | 0.089* | |
C15A | 0.3797 (5) | 0.2056 (5) | 0.5134 (2) | 0.0738 (15) | |
H15A | 0.4725 | 0.2093 | 0.5392 | 0.089* | |
C16A | 0.2425 (4) | 0.4088 (4) | 0.66796 (19) | 0.0414 (10) | |
C17A | 0.1289 (5) | 0.4656 (4) | 0.65532 (19) | 0.0462 (10) | |
H17A | 0.0355 | 0.4166 | 0.6474 | 0.055* | |
C18A | 0.1488 (5) | 0.5926 (4) | 0.6540 (2) | 0.0538 (11) | |
H18A | 0.0702 | 0.6289 | 0.6455 | 0.065* | |
C19A | 0.2871 (6) | 0.6648 (4) | 0.6657 (2) | 0.0529 (11) | |
C20A | 0.4024 (5) | 0.6118 (4) | 0.6781 (2) | 0.0584 (12) | |
H20A | 0.4955 | 0.6614 | 0.6859 | 0.070* | |
C21A | 0.3806 (5) | 0.4840 (4) | 0.6790 (2) | 0.0579 (12) | |
H21A | 0.4595 | 0.4480 | 0.6871 | 0.069* | |
Cl1B | 0.10022 (15) | −0.41962 (11) | 0.81339 (6) | 0.0782 (4) | |
Cl2B | 0.40011 (14) | 0.34687 (10) | 1.12655 (7) | 0.0738 (4) | |
O1'B | 0.0588 (3) | −0.2450 (2) | 1.21665 (13) | 0.0477 (7) | |
N2'B | 0.0175 (4) | −0.2964 (3) | 1.14330 (16) | 0.0451 (8) | |
C3'B | 0.1279 (4) | −0.2714 (3) | 1.1179 (2) | 0.0408 (9) | |
C4'B | 0.2631 (4) | −0.1922 (3) | 1.17037 (18) | 0.0391 (9) | |
H4'B | 0.3450 | −0.2297 | 1.1677 | 0.047* | |
C5'B | 0.2172 (4) | −0.2102 (3) | 1.23847 (19) | 0.0397 (9) | |
O1B | 0.2177 (3) | −0.1178 (3) | 1.35861 (14) | 0.0577 (8) | |
O2B | 0.2883 (3) | −0.4067 (2) | 1.22831 (14) | 0.0568 (8) | |
C2B | 0.2642 (5) | −0.0951 (4) | 1.2964 (2) | 0.0503 (11) | |
H2B1 | 0.3687 | −0.0675 | 1.3084 | 0.060* | |
H2B2 | 0.2256 | −0.0274 | 1.2791 | 0.060* | |
C3B | 0.2570 (4) | −0.3248 (3) | 1.2657 (2) | 0.0417 (10) | |
C4B | 0.2650 (5) | −0.4379 (4) | 1.3669 (2) | 0.0559 (12) | |
H4B | 0.2803 | −0.5068 | 1.3394 | 0.067* | |
C5B | 0.2555 (5) | −0.4440 (5) | 1.4346 (3) | 0.0710 (14) | |
H5B | 0.2635 | −0.5167 | 1.4528 | 0.085* | |
C6B | 0.2339 (5) | −0.3410 (5) | 1.4756 (2) | 0.0735 (15) | |
H6B | 0.2252 | −0.3460 | 1.5211 | 0.088* | |
C7B | 0.2249 (5) | −0.2315 (5) | 1.4505 (2) | 0.0635 (13) | |
H7B | 0.2137 | −0.1620 | 1.4791 | 0.076* | |
C8B | 0.2329 (4) | −0.2264 (4) | 1.3815 (2) | 0.0484 (10) | |
C9B | 0.2522 (4) | −0.3297 (4) | 1.3388 (2) | 0.0421 (10) | |
C10B | 0.1182 (4) | −0.3127 (3) | 1.04350 (19) | 0.0401 (9) | |
C15B | −0.0119 (5) | −0.3446 (3) | 0.9931 (2) | 0.0481 (11) | |
H15B | −0.0964 | −0.3400 | 1.0068 | 0.058* | |
C14B | −0.0187 (5) | −0.3829 (3) | 0.9230 (2) | 0.0494 (11) | |
H14B | −0.1072 | −0.4058 | 0.8899 | 0.059* | |
C13B | 0.1052 (5) | −0.3869 (4) | 0.9025 (2) | 0.0515 (11) | |
C12B | 0.2360 (5) | −0.3595 (4) | 0.9504 (2) | 0.0632 (13) | |
H12B | 0.3193 | −0.3656 | 0.9359 | 0.076* | |
C11B | 0.2422 (5) | −0.3220 (4) | 1.0217 (2) | 0.0552 (11) | |
H11B | 0.3304 | −0.3032 | 1.0548 | 0.066* | |
C16B | 0.2960 (4) | −0.0579 (3) | 1.15761 (19) | 0.0400 (9) | |
C17B | 0.4358 (4) | 0.0095 (4) | 1.1690 (2) | 0.0479 (10) | |
H17B | 0.5105 | −0.0292 | 1.1836 | 0.057* | |
C18B | 0.4693 (5) | 0.1328 (4) | 1.1594 (2) | 0.0553 (12) | |
H18B | 0.5650 | 0.1762 | 1.1668 | 0.066* | |
C19B | 0.3599 (5) | 0.1906 (4) | 1.1389 (2) | 0.0506 (11) | |
C20B | 0.2193 (5) | 0.1265 (4) | 1.1270 (2) | 0.0578 (12) | |
H20B | 0.1454 | 0.1663 | 1.1129 | 0.069* | |
C21B | 0.1874 (5) | 0.0032 (4) | 1.1359 (2) | 0.0512 (11) | |
H21B | 0.0913 | −0.0402 | 1.1272 | 0.061* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1A | 0.0918 (10) | 0.0552 (7) | 0.0494 (7) | 0.0054 (6) | 0.0072 (6) | 0.0043 (5) |
Cl2A | 0.1072 (11) | 0.0466 (7) | 0.0689 (8) | 0.0173 (7) | 0.0060 (7) | 0.0129 (6) |
O1'A | 0.0431 (18) | 0.071 (2) | 0.0545 (18) | 0.0135 (15) | 0.0109 (14) | 0.0180 (15) |
N2'A | 0.052 (2) | 0.063 (2) | 0.057 (2) | 0.0234 (19) | 0.0168 (19) | 0.0176 (19) |
C3'A | 0.041 (3) | 0.040 (2) | 0.052 (3) | 0.011 (2) | 0.008 (2) | 0.0058 (19) |
C4'A | 0.037 (2) | 0.046 (2) | 0.046 (2) | 0.008 (2) | 0.0058 (19) | 0.0096 (19) |
C5'A | 0.032 (2) | 0.044 (2) | 0.050 (2) | 0.0054 (19) | 0.0107 (19) | 0.0093 (19) |
O1A | 0.067 (2) | 0.0500 (18) | 0.0473 (17) | −0.0094 (15) | 0.0009 (15) | 0.0108 (14) |
O2A | 0.062 (2) | 0.0456 (17) | 0.0632 (19) | −0.0045 (15) | −0.0015 (17) | 0.0028 (15) |
C2A | 0.056 (3) | 0.044 (2) | 0.051 (3) | 0.001 (2) | 0.013 (2) | 0.009 (2) |
C3A | 0.036 (3) | 0.037 (2) | 0.057 (3) | 0.0086 (19) | 0.011 (2) | 0.005 (2) |
C4A | 0.050 (3) | 0.051 (3) | 0.067 (3) | 0.004 (2) | 0.016 (2) | 0.019 (2) |
C5A | 0.076 (4) | 0.059 (3) | 0.077 (4) | 0.014 (3) | 0.024 (3) | 0.030 (3) |
C6A | 0.096 (4) | 0.071 (3) | 0.058 (3) | 0.018 (3) | 0.029 (3) | 0.031 (3) |
C7A | 0.077 (4) | 0.070 (3) | 0.047 (3) | 0.008 (3) | 0.015 (2) | 0.009 (2) |
C8A | 0.050 (3) | 0.046 (2) | 0.050 (3) | 0.007 (2) | 0.017 (2) | 0.012 (2) |
C9A | 0.041 (3) | 0.044 (2) | 0.049 (2) | 0.010 (2) | 0.015 (2) | 0.013 (2) |
C10A | 0.041 (3) | 0.045 (2) | 0.048 (2) | 0.012 (2) | 0.007 (2) | 0.0037 (19) |
C11A | 0.048 (3) | 0.089 (4) | 0.060 (3) | 0.017 (3) | 0.011 (2) | 0.008 (3) |
C12A | 0.054 (3) | 0.087 (4) | 0.056 (3) | 0.017 (3) | 0.005 (3) | 0.010 (3) |
C13A | 0.067 (3) | 0.040 (2) | 0.043 (2) | 0.009 (2) | 0.007 (2) | −0.0013 (19) |
C14A | 0.057 (3) | 0.109 (4) | 0.056 (3) | 0.013 (3) | 0.021 (3) | 0.010 (3) |
C15A | 0.045 (3) | 0.116 (4) | 0.057 (3) | 0.017 (3) | 0.010 (3) | 0.013 (3) |
C16A | 0.045 (3) | 0.043 (2) | 0.038 (2) | 0.012 (2) | 0.0118 (19) | 0.0115 (18) |
C17A | 0.046 (3) | 0.052 (3) | 0.043 (2) | 0.017 (2) | 0.011 (2) | 0.012 (2) |
C18A | 0.062 (3) | 0.056 (3) | 0.051 (3) | 0.028 (3) | 0.014 (2) | 0.014 (2) |
C19A | 0.080 (4) | 0.045 (2) | 0.036 (2) | 0.017 (3) | 0.014 (2) | 0.0109 (19) |
C20A | 0.055 (3) | 0.053 (3) | 0.070 (3) | 0.008 (2) | 0.018 (2) | 0.025 (2) |
C21A | 0.049 (3) | 0.057 (3) | 0.075 (3) | 0.014 (2) | 0.019 (2) | 0.026 (2) |
Cl1B | 0.1185 (12) | 0.0726 (8) | 0.0443 (6) | 0.0201 (8) | 0.0267 (7) | 0.0072 (6) |
Cl2B | 0.0774 (9) | 0.0436 (6) | 0.0982 (10) | 0.0068 (6) | 0.0205 (7) | 0.0196 (6) |
O1'B | 0.0425 (18) | 0.0564 (17) | 0.0431 (16) | 0.0139 (14) | 0.0117 (13) | 0.0005 (13) |
N2'B | 0.044 (2) | 0.049 (2) | 0.0384 (19) | 0.0089 (17) | 0.0079 (16) | 0.0035 (16) |
C3'B | 0.044 (3) | 0.033 (2) | 0.044 (2) | 0.0097 (19) | 0.007 (2) | 0.0081 (18) |
C4'B | 0.042 (2) | 0.038 (2) | 0.039 (2) | 0.0115 (19) | 0.0113 (19) | 0.0096 (17) |
C5'B | 0.036 (2) | 0.040 (2) | 0.042 (2) | 0.0124 (19) | 0.0048 (19) | 0.0067 (18) |
O1B | 0.073 (2) | 0.0537 (18) | 0.0479 (17) | 0.0221 (16) | 0.0176 (16) | −0.0007 (14) |
O2B | 0.073 (2) | 0.0447 (17) | 0.0583 (18) | 0.0227 (16) | 0.0205 (16) | 0.0076 (14) |
C2B | 0.062 (3) | 0.044 (2) | 0.045 (2) | 0.014 (2) | 0.014 (2) | 0.003 (2) |
C3B | 0.040 (2) | 0.035 (2) | 0.046 (2) | 0.0048 (19) | 0.0094 (19) | 0.0021 (18) |
C4B | 0.061 (3) | 0.055 (3) | 0.050 (3) | 0.009 (2) | 0.012 (2) | 0.013 (2) |
C5B | 0.073 (4) | 0.075 (4) | 0.067 (3) | 0.010 (3) | 0.017 (3) | 0.029 (3) |
C6B | 0.067 (4) | 0.100 (4) | 0.046 (3) | −0.001 (3) | 0.014 (3) | 0.021 (3) |
C7B | 0.058 (3) | 0.079 (3) | 0.047 (3) | 0.008 (3) | 0.012 (2) | 0.004 (3) |
C8B | 0.039 (3) | 0.057 (3) | 0.041 (2) | 0.002 (2) | 0.004 (2) | 0.003 (2) |
C9B | 0.036 (2) | 0.044 (2) | 0.044 (2) | 0.0074 (19) | 0.0087 (19) | 0.0073 (19) |
C10B | 0.044 (3) | 0.035 (2) | 0.040 (2) | 0.0069 (19) | 0.009 (2) | 0.0073 (17) |
C15B | 0.054 (3) | 0.041 (2) | 0.045 (2) | 0.007 (2) | 0.007 (2) | 0.0056 (19) |
C14B | 0.057 (3) | 0.040 (2) | 0.043 (2) | 0.009 (2) | 0.000 (2) | 0.0062 (19) |
C13B | 0.074 (3) | 0.039 (2) | 0.040 (2) | 0.011 (2) | 0.014 (2) | 0.0079 (19) |
C12B | 0.067 (4) | 0.072 (3) | 0.053 (3) | 0.017 (3) | 0.024 (3) | 0.004 (2) |
C11B | 0.050 (3) | 0.065 (3) | 0.047 (3) | 0.014 (2) | 0.009 (2) | 0.002 (2) |
C16B | 0.042 (3) | 0.037 (2) | 0.042 (2) | 0.0103 (19) | 0.0117 (19) | 0.0060 (18) |
C17B | 0.044 (3) | 0.040 (2) | 0.057 (3) | 0.011 (2) | 0.004 (2) | 0.009 (2) |
C18B | 0.049 (3) | 0.045 (3) | 0.065 (3) | 0.004 (2) | 0.008 (2) | 0.007 (2) |
C19B | 0.062 (3) | 0.035 (2) | 0.054 (3) | 0.008 (2) | 0.017 (2) | 0.0081 (19) |
C20B | 0.057 (3) | 0.045 (3) | 0.080 (3) | 0.021 (2) | 0.017 (3) | 0.023 (2) |
C21B | 0.039 (3) | 0.043 (2) | 0.072 (3) | 0.011 (2) | 0.013 (2) | 0.015 (2) |
Geometric parameters (Å, º) top
Cl1A—C13A | 1.737 (4) | Cl1B—C13B | 1.741 (4) |
Cl2A—C19A | 1.742 (4) | Cl2B—C19B | 1.746 (4) |
O1'A—N2'A | 1.424 (4) | O1'B—N2'B | 1.425 (4) |
O1'A—C5'A | 1.462 (4) | O1'B—C5'B | 1.468 (4) |
N2'A—C3'A | 1.277 (5) | N2'B—C3'B | 1.279 (5) |
C3'A—C10A | 1.473 (5) | C3'B—C10B | 1.459 (5) |
C3'A—C4'A | 1.514 (5) | C3'B—C4'B | 1.514 (5) |
C4'A—C5'A | 1.520 (5) | C4'B—C16B | 1.513 (5) |
C4'A—C16A | 1.522 (5) | C4'B—C5'B | 1.531 (5) |
C5'A—C2A | 1.508 (5) | C5'B—C2B | 1.512 (5) |
C5'A—C3A | 1.540 (5) | C5'B—C3B | 1.524 (5) |
O1A—C8A | 1.361 (4) | O1B—C8B | 1.357 (5) |
O1A—C2A | 1.437 (4) | O1B—C2B | 1.434 (4) |
O2A—C3A | 1.212 (4) | O2B—C3B | 1.219 (4) |
C3A—C9A | 1.461 (5) | C3B—C9B | 1.463 (5) |
C4A—C5A | 1.354 (6) | C4B—C5B | 1.370 (6) |
C4A—C9A | 1.394 (5) | C4B—C9B | 1.396 (5) |
C5A—C6A | 1.381 (6) | C5B—C6B | 1.385 (6) |
C6A—C7A | 1.374 (6) | C6B—C7B | 1.374 (6) |
C7A—C8A | 1.387 (5) | C7B—C8B | 1.390 (5) |
C8A—C9A | 1.386 (5) | C8B—C9B | 1.395 (5) |
C10A—C15A | 1.372 (6) | C10B—C15B | 1.386 (5) |
C10A—C11A | 1.377 (5) | C10B—C11B | 1.387 (5) |
C11A—C12A | 1.382 (6) | C15B—C14B | 1.378 (5) |
C12A—C13A | 1.358 (6) | C14B—C13B | 1.362 (5) |
C13A—C14A | 1.365 (6) | C13B—C12B | 1.369 (6) |
C14A—C15A | 1.383 (6) | C12B—C11B | 1.400 (5) |
C16A—C17A | 1.374 (5) | C16B—C17B | 1.371 (5) |
C16A—C21A | 1.387 (5) | C16B—C21B | 1.391 (5) |
C17A—C18A | 1.376 (5) | C17B—C18B | 1.378 (5) |
C18A—C19A | 1.376 (6) | C18B—C19B | 1.367 (5) |
C19A—C20A | 1.362 (6) | C19B—C20B | 1.365 (6) |
C20A—C21A | 1.382 (5) | C20B—C21B | 1.373 (5) |
| | | |
N2'A—O1'A—C5'A | 108.6 (3) | N2'B—O1'B—C5'B | 107.8 (3) |
C3'A—N2'A—O1'A | 108.7 (3) | C3'B—N2'B—O1'B | 108.9 (3) |
N2'A—C3'A—C10A | 121.0 (4) | N2'B—C3'B—C10B | 121.3 (4) |
N2'A—C3'A—C4'A | 114.5 (4) | N2'B—C3'B—C4'B | 114.4 (3) |
C10A—C3'A—C4'A | 124.3 (4) | C10B—C3'B—C4'B | 124.3 (4) |
C3'A—C4'A—C5'A | 99.9 (3) | C16B—C4'B—C3'B | 111.1 (3) |
C3'A—C4'A—C16A | 111.0 (3) | C16B—C4'B—C5'B | 115.9 (3) |
C5'A—C4'A—C16A | 117.0 (3) | C3'B—C4'B—C5'B | 98.9 (3) |
O1'A—C5'A—C2A | 108.8 (3) | O1'B—C5'B—C2B | 108.5 (3) |
O1'A—C5'A—C4'A | 104.7 (3) | O1'B—C5'B—C3B | 104.2 (3) |
C2A—C5'A—C4'A | 117.3 (3) | C2B—C5'B—C3B | 111.1 (3) |
O1'A—C5'A—C3A | 103.2 (3) | O1'B—C5'B—C4'B | 104.1 (3) |
C2A—C5'A—C3A | 109.6 (3) | C2B—C5'B—C4'B | 115.7 (3) |
C4'A—C5'A—C3A | 112.2 (3) | C3B—C5'B—C4'B | 112.2 (3) |
C8A—O1A—C2A | 115.9 (3) | C8B—O1B—C2B | 117.5 (3) |
O1A—C2A—C5'A | 113.0 (3) | O1B—C2B—C5'B | 113.1 (3) |
O2A—C3A—C9A | 124.5 (4) | O2B—C3B—C9B | 123.1 (4) |
O2A—C3A—C5'A | 120.5 (4) | O2B—C3B—C5'B | 121.6 (3) |
C9A—C3A—C5'A | 114.7 (3) | C9B—C3B—C5'B | 115.2 (3) |
C5A—C4A—C9A | 121.2 (4) | C5B—C4B—C9B | 120.9 (4) |
C4A—C5A—C6A | 120.4 (4) | C4B—C5B—C6B | 119.4 (5) |
C7A—C6A—C5A | 119.6 (4) | C7B—C6B—C5B | 121.4 (5) |
C6A—C7A—C8A | 120.1 (5) | C6B—C7B—C8B | 118.9 (5) |
O1A—C8A—C9A | 123.2 (4) | O1B—C8B—C7B | 116.4 (4) |
O1A—C8A—C7A | 116.4 (4) | O1B—C8B—C9B | 122.8 (4) |
C9A—C8A—C7A | 120.4 (4) | C7B—C8B—C9B | 120.7 (4) |
C8A—C9A—C4A | 118.2 (4) | C8B—C9B—C4B | 118.6 (4) |
C8A—C9A—C3A | 120.8 (4) | C8B—C9B—C3B | 120.5 (4) |
C4A—C9A—C3A | 120.9 (4) | C4B—C9B—C3B | 121.0 (4) |
C15A—C10A—C11A | 117.8 (4) | C15B—C10B—C11B | 118.1 (4) |
C15A—C10A—C3'A | 121.0 (4) | C15B—C10B—C3'B | 122.2 (4) |
C11A—C10A—C3'A | 121.1 (4) | C11B—C10B—C3'B | 119.7 (4) |
C10A—C11A—C12A | 121.4 (5) | C14B—C15B—C10B | 121.3 (4) |
C13A—C12A—C11A | 119.4 (4) | C13B—C14B—C15B | 119.4 (4) |
C12A—C13A—C14A | 120.5 (4) | C14B—C13B—C12B | 121.5 (4) |
C12A—C13A—Cl1A | 120.4 (4) | C14B—C13B—Cl1B | 119.8 (4) |
C14A—C13A—Cl1A | 119.1 (4) | C12B—C13B—Cl1B | 118.6 (4) |
C13A—C14A—C15A | 119.6 (4) | C13B—C12B—C11B | 118.8 (4) |
C10A—C15A—C14A | 121.2 (4) | C10B—C11B—C12B | 120.8 (4) |
C17A—C16A—C21A | 117.7 (4) | C17B—C16B—C21B | 117.3 (4) |
C17A—C16A—C4'A | 121.1 (4) | C17B—C16B—C4'B | 120.7 (3) |
C21A—C16A—C4'A | 121.3 (4) | C21B—C16B—C4'B | 122.0 (4) |
C16A—C17A—C18A | 122.2 (4) | C16B—C17B—C18B | 122.0 (4) |
C19A—C18A—C17A | 118.7 (4) | C19B—C18B—C17B | 119.1 (4) |
C20A—C19A—C18A | 120.7 (4) | C20B—C19B—C18B | 120.6 (4) |
C20A—C19A—Cl2A | 120.1 (4) | C20B—C19B—Cl2B | 119.6 (3) |
C18A—C19A—Cl2A | 119.1 (4) | C18B—C19B—Cl2B | 119.8 (4) |
C19A—C20A—C21A | 119.8 (4) | C19B—C20B—C21B | 119.8 (4) |
C20A—C21A—C16A | 120.8 (4) | C20B—C21B—C16B | 121.2 (4) |
| | | |
C5'A—O1'A—N2'A—C3'A | 11.3 (4) | C5'B—O1'B—N2'B—C3'B | −13.5 (4) |
O1'A—N2'A—C3'A—C10A | 175.9 (3) | O1'B—N2'B—C3'B—C10B | 179.9 (3) |
O1'A—N2'A—C3'A—C4'A | 1.1 (5) | O1'B—N2'B—C3'B—C4'B | −2.7 (4) |
N2'A—C3'A—C4'A—C5'A | −12.1 (4) | N2'B—C3'B—C4'B—C16B | −105.8 (4) |
C10A—C3'A—C4'A—C5'A | 173.3 (4) | C10B—C3'B—C4'B—C16B | 71.4 (4) |
N2'A—C3'A—C4'A—C16A | 112.0 (4) | N2'B—C3'B—C4'B—C5'B | 16.5 (4) |
C10A—C3'A—C4'A—C16A | −62.7 (5) | C10B—C3'B—C4'B—C5'B | −166.2 (3) |
N2'A—O1'A—C5'A—C2A | −144.6 (3) | N2'B—O1'B—C5'B—C2B | 147.0 (3) |
N2'A—O1'A—C5'A—C4'A | −18.4 (4) | N2'B—O1'B—C5'B—C3B | −94.5 (3) |
N2'A—O1'A—C5'A—C3A | 99.1 (3) | N2'B—O1'B—C5'B—C4'B | 23.3 (3) |
C3'A—C4'A—C5'A—O1'A | 17.4 (4) | C16B—C4'B—C5'B—O1'B | 96.2 (4) |
C16A—C4'A—C5'A—O1'A | −102.4 (4) | C3'B—C4'B—C5'B—O1'B | −22.6 (3) |
C3'A—C4'A—C5'A—C2A | 138.0 (3) | C16B—C4'B—C5'B—C2B | −22.8 (5) |
C16A—C4'A—C5'A—C2A | 18.2 (5) | C3'B—C4'B—C5'B—C2B | −141.6 (3) |
C3'A—C4'A—C5'A—C3A | −93.8 (4) | C16B—C4'B—C5'B—C3B | −151.8 (3) |
C16A—C4'A—C5'A—C3A | 146.4 (3) | C3'B—C4'B—C5'B—C3B | 89.5 (3) |
C8A—O1A—C2A—C5'A | −47.6 (5) | C8B—O1B—C2B—C5'B | 44.2 (5) |
O1'A—C5'A—C2A—O1A | −57.8 (4) | O1'B—C5'B—C2B—O1B | 63.3 (4) |
C4'A—C5'A—C2A—O1A | −176.4 (3) | C3B—C5'B—C2B—O1B | −50.7 (5) |
C3A—C5'A—C2A—O1A | 54.3 (4) | C4'B—C5'B—C2B—O1B | 179.8 (3) |
O1'A—C5'A—C3A—O2A | −94.1 (4) | O1'B—C5'B—C3B—O2B | 95.5 (4) |
C2A—C5'A—C3A—O2A | 150.2 (4) | C2B—C5'B—C3B—O2B | −147.8 (4) |
C4'A—C5'A—C3A—O2A | 18.1 (5) | C4'B—C5'B—C3B—O2B | −16.5 (5) |
O1'A—C5'A—C3A—C9A | 81.0 (4) | O1'B—C5'B—C3B—C9B | −83.5 (4) |
C2A—C5'A—C3A—C9A | −34.8 (4) | C2B—C5'B—C3B—C9B | 33.3 (5) |
C4'A—C5'A—C3A—C9A | −166.9 (3) | C4'B—C5'B—C3B—C9B | 164.5 (3) |
C9A—C4A—C5A—C6A | 0.3 (7) | C9B—C4B—C5B—C6B | −0.5 (7) |
C4A—C5A—C6A—C7A | −0.2 (8) | C4B—C5B—C6B—C7B | −1.5 (8) |
C5A—C6A—C7A—C8A | 0.1 (7) | C5B—C6B—C7B—C8B | 2.3 (7) |
C2A—O1A—C8A—C9A | 19.5 (6) | C2B—O1B—C8B—C7B | 163.1 (4) |
C2A—O1A—C8A—C7A | −163.0 (4) | C2B—O1B—C8B—C9B | −18.3 (5) |
C6A—C7A—C8A—O1A | −177.7 (4) | C6B—C7B—C8B—O1B | 177.5 (4) |
C6A—C7A—C8A—C9A | −0.1 (7) | C6B—C7B—C8B—C9B | −1.1 (7) |
O1A—C8A—C9A—C4A | 177.6 (4) | O1B—C8B—C9B—C4B | −179.3 (4) |
C7A—C8A—C9A—C4A | 0.2 (6) | C7B—C8B—C9B—C4B | −0.7 (6) |
O1A—C8A—C9A—C3A | 0.1 (6) | O1B—C8B—C9B—C3B | 0.0 (6) |
C7A—C8A—C9A—C3A | −177.3 (4) | C7B—C8B—C9B—C3B | 178.5 (4) |
C5A—C4A—C9A—C8A | −0.3 (6) | C5B—C4B—C9B—C8B | 1.5 (6) |
C5A—C4A—C9A—C3A | 177.2 (4) | C5B—C4B—C9B—C3B | −177.7 (4) |
O2A—C3A—C9A—C8A | −176.2 (4) | O2B—C3B—C9B—C8B | 172.2 (4) |
C5'A—C3A—C9A—C8A | 9.0 (5) | C5'B—C3B—C9B—C8B | −8.8 (5) |
O2A—C3A—C9A—C4A | 6.3 (6) | O2B—C3B—C9B—C4B | −8.5 (6) |
C5'A—C3A—C9A—C4A | −168.5 (4) | C5'B—C3B—C9B—C4B | 170.4 (4) |
N2'A—C3'A—C10A—C15A | −30.3 (6) | N2'B—C3'B—C10B—C15B | 20.4 (6) |
C4'A—C3'A—C10A—C15A | 144.0 (4) | C4'B—C3'B—C10B—C15B | −156.7 (4) |
N2'A—C3'A—C10A—C11A | 152.2 (4) | N2'B—C3'B—C10B—C11B | −158.9 (4) |
C4'A—C3'A—C10A—C11A | −33.6 (6) | C4'B—C3'B—C10B—C11B | 24.0 (5) |
C15A—C10A—C11A—C12A | −1.3 (7) | C11B—C10B—C15B—C14B | −0.9 (6) |
C3'A—C10A—C11A—C12A | 176.4 (4) | C3'B—C10B—C15B—C14B | 179.8 (3) |
C10A—C11A—C12A—C13A | −1.5 (7) | C10B—C15B—C14B—C13B | −1.5 (6) |
C11A—C12A—C13A—C14A | 3.2 (7) | C15B—C14B—C13B—C12B | 3.1 (6) |
C11A—C12A—C13A—Cl1A | −175.0 (4) | C15B—C14B—C13B—Cl1B | −173.5 (3) |
C12A—C13A—C14A—C15A | −2.1 (7) | C14B—C13B—C12B—C11B | −2.4 (7) |
Cl1A—C13A—C14A—C15A | 176.1 (4) | Cl1B—C13B—C12B—C11B | 174.3 (3) |
C11A—C10A—C15A—C14A | 2.4 (7) | C15B—C10B—C11B—C12B | 1.6 (6) |
C3'A—C10A—C15A—C14A | −175.3 (4) | C3'B—C10B—C11B—C12B | −179.0 (4) |
C13A—C14A—C15A—C10A | −0.8 (8) | C13B—C12B—C11B—C10B | 0.0 (7) |
C3'A—C4'A—C16A—C17A | 129.9 (4) | C3'B—C4'B—C16B—C17B | −145.3 (4) |
C5'A—C4'A—C16A—C17A | −116.5 (4) | C5'B—C4'B—C16B—C17B | 102.8 (4) |
C3'A—C4'A—C16A—C21A | −50.2 (5) | C3'B—C4'B—C16B—C21B | 36.4 (5) |
C5'A—C4'A—C16A—C21A | 63.5 (5) | C5'B—C4'B—C16B—C21B | −75.4 (5) |
C21A—C16A—C17A—C18A | −0.6 (6) | C21B—C16B—C17B—C18B | −0.1 (6) |
C4'A—C16A—C17A—C18A | 179.4 (4) | C4'B—C16B—C17B—C18B | −178.5 (4) |
C16A—C17A—C18A—C19A | 0.1 (6) | C16B—C17B—C18B—C19B | 1.0 (6) |
C17A—C18A—C19A—C20A | 0.2 (6) | C17B—C18B—C19B—C20B | −1.0 (6) |
C17A—C18A—C19A—Cl2A | 179.4 (3) | C17B—C18B—C19B—Cl2B | 179.9 (3) |
C18A—C19A—C20A—C21A | 0.0 (7) | C18B—C19B—C20B—C21B | 0.2 (7) |
Cl2A—C19A—C20A—C21A | −179.2 (3) | Cl2B—C19B—C20B—C21B | 179.3 (3) |
C19A—C20A—C21A—C16A | −0.5 (7) | C19B—C20B—C21B—C16B | 0.7 (7) |
C17A—C16A—C21A—C20A | 0.7 (6) | C17B—C16B—C21B—C20B | −0.7 (6) |
C4'A—C16A—C21A—C20A | −179.2 (4) | C4'B—C16B—C21B—C20B | 177.6 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4′A—H4′A···O2A | 0.98 | 2.40 | 2.780 (5) | 103 |
C2B—H2B2···Cl1Ai | 0.97 | 2.76 | 3.600 (4) | 145 |
C5A—H5A···Cg2 | 0.93 | 2.85 | 3.740 (5) | 160 |
C6A—H6A···Cg3 | 0.93 | 2.83 | 3.671 (5) | 151 |
C17A—H17A···Cg1ii | 0.93 | 2.63 | 3.515 (5) | 159 |
C15A—H15A···Cg1iii | 0.93 | 2.74 | 3.578 (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 topRing | Molecule | q2Å | q3Å | QTÅ | φ2° | Conformation |
Ring B | I | 0.335 (4) | 0.271 (4) | 0.431 (4) | -39.7 (6) | sofa |
Ring B | II | 0.312 (4) | -0.252 (4) | 0.401 (4) | 141.0 (7) | sofa |
Ring C | I | 0.183 (4) | – | – | 140.8 (11) | envelope |
Ring C | II | 0.237 (4) | – | – | -41.5 (8) | envelope |