The title compound, C
29H
19Cl
2NO
3, crystallizes with two molecules in the asymmetric unit. The pyran ring of the flavanone moiety is puckered due to the saturation of a bond and this causes the ring to adopt a sofa conformation. The spiroisoxazoline rings adopt envelope conformations. The phenyl rings on the isoxazoline ring are perpendicular to each other. The structure is stabilized by intermolecular C—H
O and C—H
N hydrogen bonds.
Supporting information
CCDC reference: 154651
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.139
- Data-to-parameter ratio = 14.4
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
Tmin and Tmax reported: 0.638 0.762
Tmin and Tmax expected: 0.485 0.762
RR = 1.316
Please check that your absorption correction is appropriate.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
To a stirred solution of 3-p-chlorobenzylidene-4-flavanone (3 mmol) and N-(p-chlorobenzhydroxyiminoyl chloride (3 mmol) in dry CHCl3 (5 ml), 3.3 mmol of triethylamine was added. The reaction was monitored by TLC. After completion of the reaction, water was added to remove triethylamine hydrochloride and the resulting solution extracted with CHCl3. The extracts were combined and dried using MgSO4 and the product was purified by column chromatography (hexane/ethylacetate 9:1). The title compound, (I), was recrystallized from ethyl acetate/hexane.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SDP (Frenz, 1978); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: PARST97 (Nardelli, 1995) and PLATON (Spek, 1998).
Spiro[3,4-di(4-chlorophenyl)-4,5-dihydroisoxazole-5,3'-flavan-4'-one]
top
Crystal data top
C29H19Cl2NO3 | Z = 4 |
Mr = 500.35 | F(000) = 1032 |
Triclinic, P1 | Dx = 1.397 Mg m−3 |
a = 11.2032 (10) Å | Cu Kα radiation, λ = 1.5418 Å |
b = 12.349 (2) Å | Cell parameters from 25 reflections |
c = 18.973 (5) Å | θ = 14–25° |
α = 108.89 (1)° | µ = 2.72 mm−1 |
β = 105.09 (1)° | T = 293 K |
γ = 91.66 (1)° | Needle, colourless |
V = 2379.5 (8) Å3 | 0.3 × 0.25 × 0.10 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 6262 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.047 |
Graphite monochromator | θmax = 72.0°, θmin = 2.6° |
ω–2θ scans | h = −13→13 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→15 |
Tmin = 0.638, Tmax = 0.762 | l = −23→22 |
9478 measured reflections | 3 standard reflections every 200 reflections |
9032 independent reflections | intensity decay: <0.1% |
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)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.139 | w = 1/[σ2(Fo2) + (0.0735P)2 + 0.5655P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
9032 reflections | Δρmax = 0.26 e Å−3 |
629 parameters | Δρmin = −0.36 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0021 (2) |
Crystal data top
C29H19Cl2NO3 | γ = 91.66 (1)° |
Mr = 500.35 | V = 2379.5 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.2032 (10) Å | Cu Kα radiation |
b = 12.349 (2) Å | µ = 2.72 mm−1 |
c = 18.973 (5) Å | T = 293 K |
α = 108.89 (1)° | 0.3 × 0.25 × 0.10 mm |
β = 105.09 (1)° | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 6262 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.047 |
Tmin = 0.638, Tmax = 0.762 | 3 standard reflections every 200 reflections |
9478 measured reflections | intensity decay: <0.1% |
9032 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.26 e Å−3 |
9032 reflections | Δρmin = −0.36 e Å−3 |
629 parameters | |
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 | 0.03398 (7) | 0.94750 (6) | 0.40389 (4) | 0.0765 (2) | |
Cl2A | −0.19490 (9) | 1.55588 (7) | 0.20412 (5) | 0.0978 (3) | |
O1'A | −0.28032 (15) | 0.64837 (15) | −0.03368 (9) | 0.0655 (4) | |
C2'A | −0.1957 (2) | 0.7420 (2) | 0.02954 (13) | 0.0582 (6) | |
H2'A | −0.2197 | 0.7478 | 0.0766 | 0.070* | |
C4'A | −0.2010 (2) | 0.8493 (2) | −0.06300 (14) | 0.0604 (6) | |
C5'A | −0.2554 (2) | 0.7401 (2) | −0.12504 (14) | 0.0604 (6) | |
C6'A | −0.2956 (2) | 0.6469 (2) | −0.10716 (14) | 0.0583 (6) | |
O7'A | −0.15443 (19) | 0.93177 (17) | −0.07273 (11) | 0.0791 (5) | |
O1A | −0.34627 (14) | 0.86759 (16) | 0.00810 (11) | 0.0730 (5) | |
N2A | −0.35683 (19) | 0.9864 (2) | 0.03769 (14) | 0.0752 (6) | |
C3A | −0.2492 (2) | 1.0418 (2) | 0.07613 (14) | 0.0598 (6) | |
C4A | −0.14575 (19) | 0.9667 (2) | 0.08157 (13) | 0.0555 (5) | |
H4A | −0.0765 | 0.9967 | 0.0677 | 0.067* | |
C5A | −0.2143 (2) | 0.8552 (2) | 0.01638 (13) | 0.0563 (5) | |
C6A | −0.10049 (19) | 0.9611 (2) | 0.16245 (13) | 0.0536 (5) | |
C7A | −0.1838 (2) | 0.9435 (2) | 0.20150 (14) | 0.0635 (6) | |
H7A | −0.2689 | 0.9358 | 0.1776 | 0.076* | |
C8A | −0.1435 (2) | 0.9373 (2) | 0.27481 (14) | 0.0647 (6) | |
H8A | −0.2004 | 0.9234 | 0.2999 | 0.078* | |
C9A | −0.0175 (2) | 0.9518 (2) | 0.31041 (14) | 0.0578 (6) | |
C10A | 0.0675 (2) | 0.9716 (2) | 0.27416 (15) | 0.0620 (6) | |
H10A | 0.1525 | 0.9823 | 0.2992 | 0.074* | |
C11A | 0.0256 (2) | 0.9753 (2) | 0.20000 (14) | 0.0592 (6) | |
H11A | 0.0829 | 0.9876 | 0.1748 | 0.071* | |
C12A | −0.2350 (2) | 1.1679 (2) | 0.11149 (14) | 0.0610 (6) | |
C13A | −0.1187 (2) | 1.2313 (2) | 0.14837 (15) | 0.0670 (6) | |
H13A | −0.0482 | 1.1933 | 0.1539 | 0.080* | |
C14A | −0.1061 (3) | 1.3509 (2) | 0.17721 (15) | 0.0717 (7) | |
H14A | −0.0276 | 1.3931 | 0.2014 | 0.086* | |
C15A | −0.2100 (3) | 1.4063 (2) | 0.16975 (15) | 0.0704 (7) | |
C16A | −0.3271 (3) | 1.3455 (3) | 0.13483 (17) | 0.0789 (8) | |
H16A | −0.3973 | 1.3842 | 0.1309 | 0.095* | |
C17A | −0.3393 (2) | 1.2269 (3) | 0.10573 (16) | 0.0733 (7) | |
H17A | −0.4183 | 1.1855 | 0.0819 | 0.088* | |
C18A | −0.3573 (3) | 0.5463 (2) | −0.16613 (16) | 0.0707 (7) | |
H18A | −0.3856 | 0.4847 | −0.1542 | 0.085* | |
C19A | −0.3766 (3) | 0.5382 (3) | −0.24236 (17) | 0.0858 (9) | |
H19A | −0.4178 | 0.4706 | −0.2819 | 0.103* | |
C20A | −0.3358 (4) | 0.6283 (3) | −0.26063 (17) | 0.0956 (11) | |
H20A | −0.3498 | 0.6217 | −0.3125 | 0.115* | |
C21A | −0.2743 (3) | 0.7284 (3) | −0.20305 (16) | 0.0778 (8) | |
H21A | −0.2452 | 0.7887 | −0.2159 | 0.093* | |
C22A | −0.0651 (2) | 0.7112 (2) | 0.04279 (13) | 0.0578 (6) | |
C23A | −0.0339 (3) | 0.6341 (3) | 0.0813 (2) | 0.0923 (10) | |
H23A | −0.0936 | 0.6043 | 0.0984 | 0.111* | |
C24A | 0.0833 (4) | 0.6002 (4) | 0.0951 (3) | 0.1137 (13) | |
H24A | 0.1026 | 0.5494 | 0.1223 | 0.136* | |
C25A | 0.1712 (3) | 0.6415 (3) | 0.0689 (2) | 0.0958 (10) | |
H25A | 0.2500 | 0.6174 | 0.0768 | 0.115* | |
C26A | 0.1426 (3) | 0.7173 (3) | 0.0316 (2) | 0.0918 (10) | |
H26A | 0.2026 | 0.7464 | 0.0143 | 0.110* | |
C27A | 0.0261 (2) | 0.7522 (3) | 0.01848 (18) | 0.0782 (8) | |
H27A | 0.0086 | 0.8048 | −0.0074 | 0.094* | |
Cl1B | 0.52718 (8) | 0.64612 (7) | 0.07550 (5) | 0.0982 (3) | |
Cl2B | 1.02062 (8) | 1.29857 (9) | 0.37424 (6) | 0.1102 (3) | |
O1'B | 0.44224 (16) | 1.39783 (13) | 0.51642 (11) | 0.0658 (5) | |
C2'B | 0.5288 (2) | 1.32046 (18) | 0.49036 (14) | 0.0537 (5) | |
H2'B | 0.5619 | 1.3498 | 0.4561 | 0.064* | |
C4'B | 0.3844 (2) | 1.15374 (18) | 0.48322 (13) | 0.0498 (5) | |
C5'B | 0.3253 (2) | 1.24131 (18) | 0.53039 (13) | 0.0499 (5) | |
C6'B | 0.3554 (2) | 1.35809 (19) | 0.54351 (14) | 0.0546 (5) | |
O7'B | 0.36989 (15) | 1.05176 (13) | 0.47398 (10) | 0.0620 (4) | |
O1B | 0.36655 (15) | 1.21113 (14) | 0.37540 (10) | 0.0608 (4) | |
N2B | 0.35608 (18) | 1.11148 (18) | 0.30973 (12) | 0.0600 (5) | |
C3B | 0.4486 (2) | 1.05591 (19) | 0.32394 (13) | 0.0513 (5) | |
C4B | 0.54038 (19) | 1.11146 (18) | 0.40293 (12) | 0.0480 (5) | |
H4B | 0.5569 | 1.0551 | 0.4295 | 0.058* | |
C5B | 0.4621 (2) | 1.19983 (18) | 0.44106 (13) | 0.0489 (5) | |
C6B | 0.66080 (19) | 1.15896 (17) | 0.39506 (12) | 0.0476 (5) | |
C7B | 0.6600 (2) | 1.20930 (19) | 0.33940 (13) | 0.0546 (5) | |
H7B | 0.5845 | 1.2138 | 0.3061 | 0.065* | |
C8B | 0.7702 (2) | 1.2530 (2) | 0.33269 (15) | 0.0633 (6) | |
H8B | 0.7692 | 1.2865 | 0.2952 | 0.076* | |
C9B | 0.8808 (2) | 1.2460 (2) | 0.38236 (16) | 0.0664 (7) | |
C10B | 0.8840 (2) | 1.1966 (2) | 0.43766 (16) | 0.0661 (6) | |
H10B | 0.9597 | 1.1931 | 0.4711 | 0.079* | |
C11B | 0.7734 (2) | 1.1519 (2) | 0.44335 (13) | 0.0566 (5) | |
H11B | 0.7753 | 1.1168 | 0.4801 | 0.068* | |
C12B | 0.4666 (2) | 0.9537 (2) | 0.26283 (13) | 0.0545 (5) | |
C13B | 0.5244 (2) | 0.8653 (2) | 0.28150 (15) | 0.0610 (6) | |
H13B | 0.5513 | 0.8698 | 0.3332 | 0.073* | |
C14B | 0.5426 (2) | 0.7701 (2) | 0.22387 (16) | 0.0686 (7) | |
H14B | 0.5803 | 0.7102 | 0.2366 | 0.082* | |
C15B | 0.5048 (2) | 0.7647 (2) | 0.14796 (16) | 0.0692 (7) | |
C16B | 0.4506 (3) | 0.8525 (3) | 0.12843 (16) | 0.0772 (8) | |
H16B | 0.4277 | 0.8491 | 0.0769 | 0.093* | |
C17B | 0.4298 (3) | 0.9466 (2) | 0.18562 (15) | 0.0709 (7) | |
H17B | 0.3909 | 1.0055 | 0.1722 | 0.085* | |
C18B | 0.2950 (3) | 1.4409 (2) | 0.58431 (16) | 0.0699 (7) | |
H18B | 0.3156 | 1.5184 | 0.5926 | 0.084* | |
C19B | 0.2042 (3) | 1.4079 (2) | 0.61257 (16) | 0.0737 (7) | |
H19B | 0.1621 | 1.4634 | 0.6391 | 0.088* | |
C20B | 0.1747 (3) | 1.2927 (2) | 0.60186 (15) | 0.0708 (7) | |
H20B | 0.1146 | 1.2713 | 0.6223 | 0.085* | |
C21B | 0.2343 (2) | 1.2110 (2) | 0.56130 (13) | 0.0575 (6) | |
H21B | 0.2140 | 1.1338 | 0.5541 | 0.069* | |
C22B | 0.6382 (2) | 1.32612 (18) | 0.55793 (13) | 0.0538 (5) | |
C23B | 0.7385 (3) | 1.4093 (2) | 0.57932 (17) | 0.0733 (7) | |
H23B | 0.7361 | 1.4607 | 0.5526 | 0.088* | |
C24B | 0.8418 (3) | 1.4171 (3) | 0.63952 (19) | 0.0920 (10) | |
H24B | 0.9093 | 1.4724 | 0.6522 | 0.110* | |
C25B | 0.8461 (2) | 1.34455 (19) | 0.68079 (12) | 0.0884 (9) | |
H25B | 0.9157 | 1.3508 | 0.7220 | 0.106* | |
C26B | 0.7469 (2) | 1.26223 (19) | 0.66103 (12) | 0.0780 (8) | |
H26B | 0.7488 | 1.2130 | 0.6894 | 0.094* | |
C27B | 0.6443 (2) | 1.2520 (2) | 0.59938 (15) | 0.0637 (6) | |
H27B | 0.5785 | 1.1944 | 0.5856 | 0.076* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1A | 0.0803 (4) | 0.0854 (5) | 0.0584 (4) | −0.0008 (3) | 0.0091 (3) | 0.0268 (3) |
Cl2A | 0.1323 (7) | 0.0787 (5) | 0.0910 (5) | 0.0209 (5) | 0.0514 (5) | 0.0242 (4) |
O1'A | 0.0613 (10) | 0.0745 (11) | 0.0558 (9) | −0.0150 (8) | 0.0125 (8) | 0.0211 (8) |
C2'A | 0.0510 (12) | 0.0709 (15) | 0.0509 (12) | −0.0086 (10) | 0.0141 (10) | 0.0202 (11) |
C4'A | 0.0557 (13) | 0.0683 (15) | 0.0585 (14) | 0.0032 (11) | 0.0120 (11) | 0.0273 (12) |
C5'A | 0.0655 (14) | 0.0619 (14) | 0.0545 (13) | 0.0115 (11) | 0.0151 (11) | 0.0220 (11) |
C6'A | 0.0536 (13) | 0.0667 (14) | 0.0527 (13) | 0.0069 (11) | 0.0113 (10) | 0.0213 (11) |
O7'A | 0.0930 (14) | 0.0791 (12) | 0.0644 (11) | −0.0110 (10) | 0.0127 (10) | 0.0330 (9) |
O1A | 0.0399 (8) | 0.0818 (12) | 0.0788 (12) | −0.0021 (8) | 0.0090 (8) | 0.0103 (9) |
N2A | 0.0442 (11) | 0.0857 (16) | 0.0778 (15) | 0.0066 (10) | 0.0049 (10) | 0.0143 (12) |
C3A | 0.0456 (12) | 0.0726 (15) | 0.0555 (13) | 0.0041 (11) | 0.0097 (10) | 0.0186 (11) |
C4A | 0.0390 (11) | 0.0698 (14) | 0.0546 (13) | −0.0015 (10) | 0.0104 (10) | 0.0201 (11) |
C5A | 0.0397 (11) | 0.0702 (14) | 0.0560 (13) | −0.0010 (10) | 0.0121 (10) | 0.0195 (11) |
C6A | 0.0385 (10) | 0.0646 (13) | 0.0527 (12) | −0.0035 (9) | 0.0099 (9) | 0.0167 (10) |
C7A | 0.0370 (11) | 0.0890 (18) | 0.0577 (14) | −0.0050 (11) | 0.0111 (10) | 0.0194 (12) |
C8A | 0.0488 (13) | 0.0859 (17) | 0.0542 (13) | −0.0074 (11) | 0.0167 (11) | 0.0171 (12) |
C9A | 0.0540 (13) | 0.0575 (13) | 0.0555 (13) | −0.0044 (10) | 0.0097 (10) | 0.0165 (10) |
C10A | 0.0393 (11) | 0.0747 (15) | 0.0669 (15) | −0.0062 (10) | 0.0032 (10) | 0.0283 (12) |
C11A | 0.0400 (11) | 0.0734 (15) | 0.0672 (15) | −0.0036 (10) | 0.0153 (11) | 0.0288 (12) |
C12A | 0.0514 (13) | 0.0763 (16) | 0.0509 (13) | 0.0082 (11) | 0.0114 (10) | 0.0187 (11) |
C13A | 0.0559 (14) | 0.0764 (17) | 0.0618 (15) | 0.0081 (12) | 0.0102 (12) | 0.0198 (13) |
C14A | 0.0708 (17) | 0.0751 (17) | 0.0617 (15) | 0.0018 (13) | 0.0158 (13) | 0.0168 (13) |
C15A | 0.0855 (19) | 0.0736 (17) | 0.0546 (14) | 0.0148 (14) | 0.0271 (14) | 0.0192 (12) |
C16A | 0.0708 (18) | 0.095 (2) | 0.0783 (19) | 0.0294 (16) | 0.0301 (15) | 0.0307 (16) |
C17A | 0.0554 (14) | 0.0877 (19) | 0.0735 (17) | 0.0121 (13) | 0.0190 (13) | 0.0226 (14) |
C18A | 0.0743 (17) | 0.0605 (15) | 0.0687 (16) | 0.0081 (12) | 0.0102 (13) | 0.0187 (12) |
C19A | 0.114 (2) | 0.0631 (17) | 0.0601 (16) | 0.0200 (16) | 0.0051 (16) | 0.0092 (13) |
C20A | 0.150 (3) | 0.0754 (19) | 0.0542 (16) | 0.036 (2) | 0.0169 (18) | 0.0205 (14) |
C21A | 0.106 (2) | 0.0720 (17) | 0.0578 (15) | 0.0205 (15) | 0.0194 (15) | 0.0278 (13) |
C22A | 0.0546 (13) | 0.0693 (14) | 0.0511 (12) | −0.0026 (11) | 0.0133 (10) | 0.0249 (11) |
C23A | 0.082 (2) | 0.109 (2) | 0.120 (3) | 0.0121 (18) | 0.0401 (19) | 0.075 (2) |
C24A | 0.092 (2) | 0.137 (3) | 0.155 (4) | 0.035 (2) | 0.037 (2) | 0.103 (3) |
C25A | 0.0668 (19) | 0.118 (3) | 0.120 (3) | 0.0221 (18) | 0.0233 (18) | 0.064 (2) |
C26A | 0.0566 (16) | 0.134 (3) | 0.111 (2) | 0.0150 (17) | 0.0249 (16) | 0.076 (2) |
C27A | 0.0552 (15) | 0.108 (2) | 0.098 (2) | 0.0111 (14) | 0.0253 (14) | 0.0672 (18) |
Cl1B | 0.0988 (6) | 0.0930 (5) | 0.0856 (5) | −0.0106 (4) | 0.0461 (4) | −0.0057 (4) |
Cl2B | 0.0697 (5) | 0.1307 (7) | 0.1327 (7) | −0.0221 (5) | 0.0418 (5) | 0.0414 (6) |
O1'B | 0.0727 (11) | 0.0487 (8) | 0.0993 (13) | 0.0145 (7) | 0.0484 (10) | 0.0365 (9) |
C2'B | 0.0578 (13) | 0.0463 (11) | 0.0695 (14) | 0.0065 (9) | 0.0323 (11) | 0.0254 (10) |
C4'B | 0.0468 (11) | 0.0470 (11) | 0.0582 (13) | 0.0007 (9) | 0.0149 (10) | 0.0221 (10) |
C5'B | 0.0498 (12) | 0.0499 (11) | 0.0524 (12) | 0.0018 (9) | 0.0163 (10) | 0.0198 (9) |
C6'B | 0.0584 (13) | 0.0507 (12) | 0.0642 (14) | 0.0057 (10) | 0.0261 (11) | 0.0256 (10) |
O7'B | 0.0653 (10) | 0.0466 (8) | 0.0851 (12) | 0.0036 (7) | 0.0335 (9) | 0.0281 (8) |
O1B | 0.0599 (9) | 0.0670 (10) | 0.0643 (10) | 0.0172 (8) | 0.0175 (8) | 0.0336 (8) |
N2B | 0.0537 (11) | 0.0693 (12) | 0.0599 (12) | 0.0022 (9) | 0.0150 (9) | 0.0277 (10) |
C3B | 0.0472 (12) | 0.0561 (12) | 0.0537 (12) | −0.0016 (9) | 0.0132 (10) | 0.0244 (10) |
C4B | 0.0468 (11) | 0.0479 (11) | 0.0521 (12) | 0.0026 (9) | 0.0148 (9) | 0.0206 (9) |
C5B | 0.0489 (11) | 0.0489 (11) | 0.0557 (12) | 0.0046 (9) | 0.0162 (10) | 0.0260 (10) |
C6B | 0.0473 (11) | 0.0459 (11) | 0.0487 (11) | 0.0023 (8) | 0.0155 (9) | 0.0139 (9) |
C7B | 0.0522 (12) | 0.0584 (13) | 0.0562 (13) | 0.0028 (10) | 0.0148 (10) | 0.0245 (10) |
C8B | 0.0678 (16) | 0.0622 (14) | 0.0667 (15) | −0.0017 (11) | 0.0284 (13) | 0.0248 (12) |
C9B | 0.0573 (14) | 0.0637 (15) | 0.0742 (16) | −0.0062 (11) | 0.0276 (13) | 0.0126 (12) |
C10B | 0.0460 (12) | 0.0748 (16) | 0.0692 (16) | 0.0044 (11) | 0.0119 (11) | 0.0176 (13) |
C11B | 0.0505 (12) | 0.0626 (13) | 0.0549 (13) | 0.0064 (10) | 0.0141 (10) | 0.0183 (11) |
C12B | 0.0473 (12) | 0.0585 (13) | 0.0538 (12) | −0.0097 (10) | 0.0128 (10) | 0.0167 (10) |
C13B | 0.0621 (14) | 0.0626 (14) | 0.0586 (14) | −0.0001 (11) | 0.0195 (11) | 0.0201 (11) |
C14B | 0.0652 (15) | 0.0626 (15) | 0.0771 (17) | 0.0004 (12) | 0.0275 (13) | 0.0177 (13) |
C15B | 0.0594 (14) | 0.0701 (16) | 0.0667 (16) | −0.0165 (12) | 0.0262 (12) | 0.0043 (13) |
C16B | 0.0767 (18) | 0.088 (2) | 0.0525 (14) | −0.0116 (15) | 0.0119 (13) | 0.0119 (14) |
C17B | 0.0721 (16) | 0.0764 (17) | 0.0564 (15) | −0.0017 (13) | 0.0090 (13) | 0.0207 (13) |
C18B | 0.0836 (18) | 0.0530 (13) | 0.0837 (18) | 0.0107 (12) | 0.0415 (15) | 0.0233 (12) |
C19B | 0.0841 (18) | 0.0669 (16) | 0.0787 (18) | 0.0120 (13) | 0.0471 (15) | 0.0172 (13) |
C20B | 0.0732 (16) | 0.0718 (16) | 0.0700 (16) | −0.0035 (13) | 0.0381 (14) | 0.0147 (13) |
C21B | 0.0565 (13) | 0.0574 (13) | 0.0577 (13) | −0.0064 (10) | 0.0205 (11) | 0.0164 (10) |
C22B | 0.0573 (13) | 0.0436 (11) | 0.0610 (13) | 0.0016 (9) | 0.0259 (11) | 0.0118 (10) |
C23B | 0.0801 (18) | 0.0592 (15) | 0.0745 (17) | −0.0136 (13) | 0.0273 (15) | 0.0126 (13) |
C24B | 0.081 (2) | 0.089 (2) | 0.084 (2) | −0.0270 (17) | 0.0154 (17) | 0.0101 (17) |
C25B | 0.0687 (18) | 0.094 (2) | 0.077 (2) | 0.0001 (16) | 0.0057 (15) | 0.0074 (17) |
C26B | 0.0759 (18) | 0.0768 (18) | 0.0783 (19) | 0.0081 (14) | 0.0145 (15) | 0.0286 (15) |
C27B | 0.0599 (14) | 0.0588 (14) | 0.0717 (16) | −0.0012 (11) | 0.0156 (12) | 0.0245 (12) |
Geometric parameters (Å, º) top
Cl1A—C9A | 1.735 (2) | Cl1B—C15B | 1.730 (3) |
Cl2A—C15A | 1.735 (3) | Cl2B—C9B | 1.741 (2) |
O1'A—C6'A | 1.354 (3) | O1'B—C6'B | 1.359 (2) |
O1'A—C2'A | 1.456 (3) | O1'B—C2'B | 1.448 (3) |
C2'A—C22A | 1.501 (3) | C2'B—C22B | 1.506 (3) |
C2'A—C5A | 1.509 (3) | C2'B—C5B | 1.524 (3) |
C2'A—H2'A | 0.9800 | C2'B—H2'B | 0.9800 |
C4'A—O7'A | 1.218 (3) | C4'B—O7'B | 1.214 (2) |
C4'A—C5'A | 1.459 (3) | C4'B—C5'B | 1.460 (3) |
C4'A—C5A | 1.531 (3) | C4'B—C5B | 1.533 (3) |
C5'A—C6'A | 1.394 (3) | C5'B—C21B | 1.399 (3) |
C5'A—C21A | 1.397 (3) | C5'B—C6'B | 1.397 (3) |
C6'A—C18A | 1.386 (3) | C6'B—C18B | 1.380 (3) |
O1A—N2A | 1.412 (3) | O1B—N2B | 1.415 (3) |
O1A—C5A | 1.463 (3) | O1B—C5B | 1.465 (3) |
N2A—C3A | 1.275 (3) | N2B—C3B | 1.278 (3) |
C3A—C12A | 1.467 (3) | C3B—C12B | 1.472 (3) |
C3A—C4A | 1.508 (3) | C3B—C4B | 1.505 (3) |
C4A—C6A | 1.511 (3) | C4B—C6B | 1.517 (3) |
C4A—C5A | 1.536 (3) | C4B—C5B | 1.535 (3) |
C4A—H4A | 0.9800 | C4B—H4B | 0.9800 |
C6A—C11A | 1.383 (3) | C6B—C11B | 1.377 (3) |
C6A—C7A | 1.386 (3) | C6B—C7B | 1.386 (3) |
C7A—C8A | 1.374 (3) | C7B—C8B | 1.386 (3) |
C7A—H7A | 0.9300 | C7B—H7B | 0.9300 |
C8A—C9A | 1.375 (3) | C8B—C9B | 1.372 (4) |
C8A—H8A | 0.9300 | C8B—H8B | 0.9300 |
C9A—C10A | 1.370 (3) | C9B—C10B | 1.367 (4) |
C10A—C11A | 1.379 (3) | C10B—C11B | 1.385 (3) |
C10A—H10A | 0.9300 | C10B—H10B | 0.9300 |
C11A—H11A | 0.9300 | C11B—H11B | 0.9300 |
C12A—C13A | 1.383 (3) | C12B—C13B | 1.382 (3) |
C12A—C17A | 1.393 (4) | C12B—C17B | 1.387 (3) |
C13A—C14A | 1.388 (4) | C13B—C14B | 1.384 (3) |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.366 (4) | C14B—C15B | 1.370 (4) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—C16A | 1.375 (4) | C15B—C16B | 1.365 (4) |
C16A—C17A | 1.377 (4) | C16B—C17B | 1.383 (4) |
C16A—H16A | 0.9300 | C16B—H16B | 0.9300 |
C17A—H17A | 0.9300 | C17B—H17B | 0.9300 |
C18A—C19A | 1.375 (4) | C18B—C19B | 1.375 (3) |
C18A—H18A | 0.9300 | C18B—H18B | 0.9300 |
C19A—C20A | 1.368 (5) | C19B—C20B | 1.388 (4) |
C19A—H19A | 0.9300 | C19B—H19B | 0.9300 |
C20A—C21A | 1.371 (4) | C20B—C21B | 1.364 (3) |
C20A—H20A | 0.9300 | C20B—H20B | 0.9300 |
C21A—H21A | 0.9300 | C21B—H21B | 0.9300 |
C22A—C27A | 1.371 (3) | C22B—C27B | 1.380 (3) |
C22A—C23A | 1.377 (4) | C22B—C23B | 1.381 (3) |
C23A—C24A | 1.375 (5) | C23B—C24B | 1.373 (4) |
C23A—H23A | 0.9300 | C23B—H23B | 0.9300 |
C24A—C25A | 1.367 (5) | C24B—C25B | 1.362 (4) |
C24A—H24A | 0.9300 | C24B—H24B | 0.9300 |
C25A—C26A | 1.345 (4) | C25B—C26B | 1.3710 |
C25A—H25A | 0.9300 | C25B—H25B | 0.9300 |
C26A—C27A | 1.373 (4) | C26B—C27B | 1.379 (3) |
C26A—H26A | 0.9300 | C26B—H26B | 0.9300 |
C27A—H27A | 0.9300 | C27B—H27B | 0.9300 |
| | | |
C6'A—O1'A—C2'A | 117.90 (17) | C6'B—O1'B—C2'B | 117.77 (16) |
O1'A—C2'A—C22A | 109.9 (2) | O1'B—C2'B—C22B | 110.43 (18) |
O1'A—C2'A—C5A | 110.38 (19) | O1'B—C2'B—C5B | 111.10 (18) |
C22A—C2'A—C5A | 116.16 (18) | C22B—C2'B—C5B | 115.20 (18) |
O1'A—C2'A—H2'A | 106.6 | O1'B—C2'B—H2'B | 106.5 |
C22A—C2'A—H2'A | 106.6 | C22B—C2'B—H2'B | 106.5 |
C5A—C2'A—H2'A | 106.6 | C5B—C2'B—H2'B | 106.5 |
O7'A—C4'A—C5'A | 124.2 (2) | O7'B—C4'B—C5'B | 124.19 (19) |
O7'A—C4'A—C5A | 121.8 (2) | O7'B—C4'B—C5B | 121.48 (19) |
C5'A—C4'A—C5A | 113.9 (2) | C5'B—C4'B—C5B | 114.23 (17) |
C6'A—C5'A—C21A | 118.8 (2) | C21B—C5'B—C6'B | 118.1 (2) |
C6'A—C5'A—C4'A | 119.9 (2) | C21B—C5'B—C4'B | 121.34 (19) |
C21A—C5'A—C4'A | 121.1 (2) | C6'B—C5'B—C4'B | 120.52 (19) |
O1'A—C6'A—C18A | 116.1 (2) | O1'B—C6'B—C18B | 115.7 (2) |
O1'A—C6'A—C5'A | 123.7 (2) | O1'B—C6'B—C5'B | 123.4 (2) |
C18A—C6'A—C5'A | 120.2 (2) | C18B—C6'B—C5'B | 120.9 (2) |
N2A—O1A—C5A | 107.82 (16) | N2B—O1B—C5B | 108.07 (16) |
C3A—N2A—O1A | 109.4 (2) | C3B—N2B—O1B | 109.26 (18) |
N2A—C3A—C12A | 119.8 (2) | N2B—C3B—C12B | 120.5 (2) |
N2A—C3A—C4A | 114.3 (2) | N2B—C3B—C4B | 114.4 (2) |
C12A—C3A—C4A | 125.9 (2) | C12B—C3B—C4B | 124.7 (2) |
C3A—C4A—C6A | 110.89 (19) | C3B—C4B—C6B | 110.06 (17) |
C3A—C4A—C5A | 98.77 (18) | C3B—C4B—C5B | 99.35 (17) |
C6A—C4A—C5A | 116.8 (2) | C6B—C4B—C5B | 116.82 (17) |
C3A—C4A—H4A | 109.9 | C3B—C4B—H4B | 110.0 |
C6A—C4A—H4A | 109.9 | C6B—C4B—H4B | 110.0 |
C5A—C4A—H4A | 109.9 | C5B—C4B—H4B | 110.0 |
O1A—C5A—C2'A | 105.81 (18) | O1B—C5B—C2'B | 107.00 (17) |
O1A—C5A—C4'A | 102.94 (18) | O1B—C5B—C4'B | 102.43 (16) |
C2'A—C5A—C4'A | 111.3 (2) | C2'B—C5B—C4'B | 111.53 (18) |
O1A—C5A—C4A | 104.12 (18) | O1B—C5B—C4B | 104.21 (17) |
C2'A—C5A—C4A | 118.4 (2) | C2'B—C5B—C4B | 116.80 (17) |
C4'A—C5A—C4A | 112.48 (19) | C4'B—C5B—C4B | 113.30 (17) |
C11A—C6A—C7A | 118.2 (2) | C11B—C6B—C7B | 118.9 (2) |
C11A—C6A—C4A | 120.73 (19) | C11B—C6B—C4B | 120.03 (19) |
C7A—C6A—C4A | 121.0 (2) | C7B—C6B—C4B | 121.11 (19) |
C8A—C7A—C6A | 121.4 (2) | C8B—C7B—C6B | 120.9 (2) |
C8A—C7A—H7A | 119.3 | C8B—C7B—H7B | 119.6 |
C6A—C7A—H7A | 119.3 | C6B—C7B—H7B | 119.6 |
C7A—C8A—C9A | 118.8 (2) | C9B—C8B—C7B | 118.8 (2) |
C7A—C8A—H8A | 120.6 | C9B—C8B—H8B | 120.6 |
C9A—C8A—H8A | 120.6 | C7B—C8B—H8B | 120.6 |
C10A—C9A—C8A | 121.4 (2) | C10B—C9B—C8B | 121.4 (2) |
C10A—C9A—Cl1A | 119.59 (18) | C10B—C9B—Cl2B | 118.9 (2) |
C8A—C9A—Cl1A | 119.03 (19) | C8B—C9B—Cl2B | 119.7 (2) |
C9A—C10A—C11A | 119.1 (2) | C9B—C10B—C11B | 119.4 (2) |
C9A—C10A—H10A | 120.4 | C9B—C10B—H10B | 120.3 |
C11A—C10A—H10A | 120.4 | C11B—C10B—H10B | 120.3 |
C10A—C11A—C6A | 121.1 (2) | C6B—C11B—C10B | 120.6 (2) |
C10A—C11A—H11A | 119.5 | C6B—C11B—H11B | 119.7 |
C6A—C11A—H11A | 119.5 | C10B—C11B—H11B | 119.7 |
C13A—C12A—C17A | 118.4 (3) | C13B—C12B—C17B | 118.8 (2) |
C13A—C12A—C3A | 121.2 (2) | C13B—C12B—C3B | 120.7 (2) |
C17A—C12A—C3A | 120.3 (2) | C17B—C12B—C3B | 120.4 (2) |
C12A—C13A—C14A | 120.7 (3) | C12B—C13B—C14B | 120.5 (2) |
C12A—C13A—H13A | 119.7 | C12B—C13B—H13B | 119.8 |
C14A—C13A—H13A | 119.7 | C14B—C13B—H13B | 119.8 |
C15A—C14A—C13A | 119.5 (3) | C15B—C14B—C13B | 119.6 (3) |
C15A—C14A—H14A | 120.2 | C15B—C14B—H14B | 120.2 |
C13A—C14A—H14A | 120.2 | C13B—C14B—H14B | 120.2 |
C14A—C15A—C16A | 121.1 (3) | C16B—C15B—C14B | 120.9 (3) |
C14A—C15A—Cl2A | 119.8 (2) | C16B—C15B—Cl1B | 119.1 (2) |
C16A—C15A—Cl2A | 119.1 (2) | C14B—C15B—Cl1B | 120.0 (2) |
C15A—C16A—C17A | 119.3 (3) | C15B—C16B—C17B | 119.7 (3) |
C15A—C16A—H16A | 120.4 | C15B—C16B—H16B | 120.2 |
C17A—C16A—H16A | 120.4 | C17B—C16B—H16B | 120.2 |
C16A—C17A—C12A | 121.0 (3) | C16B—C17B—C12B | 120.5 (3) |
C16A—C17A—H17A | 119.5 | C16B—C17B—H17B | 119.8 |
C12A—C17A—H17A | 119.5 | C12B—C17B—H17B | 119.8 |
C19A—C18A—C6'A | 119.6 (3) | C19B—C18B—C6'B | 119.5 (2) |
C19A—C18A—H18A | 120.2 | C19B—C18B—H18B | 120.3 |
C6'A—C18A—H18A | 120.2 | C6'B—C18B—H18B | 120.3 |
C20A—C19A—C18A | 120.8 (3) | C18B—C19B—C20B | 120.7 (2) |
C20A—C19A—H19A | 119.6 | C18B—C19B—H19B | 119.7 |
C18A—C19A—H19A | 119.6 | C20B—C19B—H19B | 119.7 |
C19A—C20A—C21A | 120.5 (3) | C21B—C20B—C19B | 119.7 (2) |
C19A—C20A—H20A | 119.8 | C21B—C20B—H20B | 120.1 |
C21A—C20A—H20A | 119.8 | C19B—C20B—H20B | 120.1 |
C20A—C21A—C5'A | 120.1 (3) | C20B—C21B—C5'B | 121.1 (2) |
C20A—C21A—H21A | 119.9 | C20B—C21B—H21B | 119.5 |
C5'A—C21A—H21A | 119.9 | C5'B—C21B—H21B | 119.5 |
C27A—C22A—C23A | 116.9 (2) | C27B—C22B—C23B | 118.0 (2) |
C27A—C22A—C2'A | 125.2 (2) | C27B—C22B—C2'B | 123.6 (2) |
C23A—C22A—C2'A | 117.9 (2) | C23B—C22B—C2'B | 118.4 (2) |
C24A—C23A—C22A | 121.8 (3) | C24B—C23B—C22B | 121.0 (3) |
C24A—C23A—H23A | 119.1 | C24B—C23B—H23B | 119.5 |
C22A—C23A—H23A | 119.1 | C22B—C23B—H23B | 119.5 |
C25A—C24A—C23A | 119.7 (3) | C25B—C24B—C23B | 120.5 (3) |
C25A—C24A—H24A | 120.1 | C25B—C24B—H24B | 119.7 |
C23A—C24A—H24A | 120.1 | C23B—C24B—H24B | 119.7 |
C26A—C25A—C24A | 119.3 (3) | C24B—C25B—C26B | 119.38 (16) |
C26A—C25A—H25A | 120.3 | C24B—C25B—H25B | 120.3 |
C24A—C25A—H25A | 120.3 | C26B—C25B—H25B | 120.3 |
C25A—C26A—C27A | 121.0 (3) | C25B—C26B—C27B | 120.37 (14) |
C25A—C26A—H26A | 119.5 | C25B—C26B—H26B | 119.8 |
C27A—C26A—H26A | 119.5 | C27B—C26B—H26B | 119.8 |
C22A—C27A—C26A | 121.3 (3) | C26B—C27B—C22B | 120.7 (2) |
C22A—C27A—H27A | 119.3 | C26B—C27B—H27B | 119.6 |
C26A—C27A—H27A | 119.3 | C22B—C27B—H27B | 119.6 |
| | | |
C6'A—O1'A—C2'A—C22A | −86.6 (2) | C6'B—O1'B—C2'B—C22B | −85.3 (2) |
C6'A—O1'A—C2'A—C5A | 42.9 (3) | C6'B—O1'B—C2'B—C5B | 43.8 (3) |
O7'A—C4'A—C5'A—C6'A | 173.7 (3) | O7'B—C4'B—C5'B—C21B | −7.9 (4) |
C5A—C4'A—C5'A—C6'A | −9.9 (3) | C5B—C4'B—C5'B—C21B | 168.5 (2) |
O7'A—C4'A—C5'A—C21A | −9.6 (4) | O7'B—C4'B—C5'B—C6'B | 174.4 (2) |
C5A—C4'A—C5'A—C21A | 166.7 (2) | C5B—C4'B—C5'B—C6'B | −9.2 (3) |
C2'A—O1'A—C6'A—C18A | 168.2 (2) | C2'B—O1'B—C6'B—C18B | 165.2 (2) |
C2'A—O1'A—C6'A—C5'A | −13.2 (3) | C2'B—O1'B—C6'B—C5'B | −16.1 (3) |
C21A—C5'A—C6'A—O1'A | 179.0 (2) | C21B—C5'B—C6'B—O1'B | 180.0 (2) |
C4'A—C5'A—C6'A—O1'A | −4.3 (4) | C4'B—C5'B—C6'B—O1'B | −2.3 (4) |
C21A—C5'A—C6'A—C18A | −2.5 (4) | C21B—C5'B—C6'B—C18B | −1.4 (4) |
C4'A—C5'A—C6'A—C18A | 174.2 (2) | C4'B—C5'B—C6'B—C18B | 176.3 (2) |
C5A—O1A—N2A—C3A | −13.4 (3) | C5B—O1B—N2B—C3B | −13.1 (2) |
O1A—N2A—C3A—C12A | 178.7 (2) | O1B—N2B—C3B—C12B | −174.69 (17) |
O1A—N2A—C3A—C4A | −2.3 (3) | O1B—N2B—C3B—C4B | −1.1 (2) |
N2A—C3A—C4A—C6A | −107.4 (2) | N2B—C3B—C4B—C6B | −109.4 (2) |
C12A—C3A—C4A—C6A | 71.5 (3) | C12B—C3B—C4B—C6B | 63.8 (3) |
N2A—C3A—C4A—C5A | 15.8 (3) | N2B—C3B—C4B—C5B | 13.7 (2) |
C12A—C3A—C4A—C5A | −165.3 (2) | C12B—C3B—C4B—C5B | −173.02 (19) |
N2A—O1A—C5A—C2'A | 148.3 (2) | N2B—O1B—C5B—C2'B | 145.43 (16) |
N2A—O1A—C5A—C4'A | −94.8 (2) | N2B—O1B—C5B—C4'B | −97.16 (18) |
N2A—O1A—C5A—C4A | 22.7 (2) | N2B—O1B—C5B—C4B | 21.11 (19) |
O1'A—C2'A—C5A—O1A | 56.2 (2) | O1'B—C2'B—C5B—O1B | 58.1 (2) |
C22A—C2'A—C5A—O1A | −177.86 (19) | C22B—C2'B—C5B—O1B | −175.36 (17) |
O1'A—C2'A—C5A—C4'A | −55.0 (2) | O1'B—C2'B—C5B—C4'B | −53.1 (2) |
C22A—C2'A—C5A—C4'A | 71.0 (2) | C22B—C2'B—C5B—C4'B | 73.4 (2) |
O1'A—C2'A—C5A—C4A | 172.36 (18) | O1'B—C2'B—C5B—C4B | 174.35 (17) |
C22A—C2'A—C5A—C4A | −61.7 (3) | C22B—C2'B—C5B—C4B | −59.1 (2) |
O7'A—C4'A—C5A—O1A | 102.7 (3) | O7'B—C4'B—C5B—O1B | 98.7 (2) |
C5'A—C4'A—C5A—O1A | −73.8 (2) | C5'B—C4'B—C5B—O1B | −77.9 (2) |
O7'A—C4'A—C5A—C2'A | −144.4 (2) | O7'B—C4'B—C5B—C2'B | −147.2 (2) |
C5'A—C4'A—C5A—C2'A | 39.2 (3) | C5'B—C4'B—C5B—C2'B | 36.3 (3) |
O7'A—C4'A—C5A—C4A | −8.8 (3) | O7'B—C4'B—C5B—C4B | −13.0 (3) |
C5'A—C4'A—C5A—C4A | 174.7 (2) | C5'B—C4'B—C5B—C4B | 170.52 (18) |
C3A—C4A—C5A—O1A | −21.9 (2) | C3B—C4B—C5B—O1B | −19.88 (18) |
C6A—C4A—C5A—O1A | 97.0 (2) | C6B—C4B—C5B—O1B | 98.3 (2) |
C3A—C4A—C5A—C2'A | −139.0 (2) | C3B—C4B—C5B—C2'B | −137.64 (18) |
C6A—C4A—C5A—C2'A | −20.1 (3) | C6B—C4B—C5B—C2'B | −19.4 (3) |
C3A—C4A—C5A—C4'A | 88.8 (2) | C3B—C4B—C5B—C4'B | 90.7 (2) |
C6A—C4A—C5A—C4'A | −152.31 (19) | C6B—C4B—C5B—C4'B | −151.13 (19) |
C3A—C4A—C6A—C11A | −133.5 (2) | C3B—C4B—C6B—C11B | −142.3 (2) |
C5A—C4A—C6A—C11A | 114.4 (2) | C5B—C4B—C6B—C11B | 105.4 (2) |
C3A—C4A—C6A—C7A | 45.4 (3) | C3B—C4B—C6B—C7B | 37.3 (3) |
C5A—C4A—C6A—C7A | −66.7 (3) | C5B—C4B—C6B—C7B | −74.9 (3) |
C11A—C6A—C7A—C8A | −1.7 (4) | C11B—C6B—C7B—C8B | −0.7 (3) |
C4A—C6A—C7A—C8A | 179.4 (2) | C4B—C6B—C7B—C8B | 179.7 (2) |
C6A—C7A—C8A—C9A | 1.7 (4) | C6B—C7B—C8B—C9B | −0.2 (4) |
C7A—C8A—C9A—C10A | −0.4 (4) | C7B—C8B—C9B—C10B | 0.3 (4) |
C7A—C8A—C9A—Cl1A | 178.4 (2) | C7B—C8B—C9B—Cl2B | 179.15 (19) |
C8A—C9A—C10A—C11A | −0.9 (4) | C8B—C9B—C10B—C11B | 0.5 (4) |
Cl1A—C9A—C10A—C11A | −179.69 (19) | Cl2B—C9B—C10B—C11B | −178.41 (19) |
C9A—C10A—C11A—C6A | 0.9 (4) | C7B—C6B—C11B—C10B | 1.4 (3) |
C7A—C6A—C11A—C10A | 0.3 (4) | C4B—C6B—C11B—C10B | −178.9 (2) |
C4A—C6A—C11A—C10A | 179.3 (2) | C9B—C10B—C11B—C6B | −1.4 (4) |
N2A—C3A—C12A—C13A | −175.0 (3) | N2B—C3B—C12B—C13B | −150.3 (2) |
C4A—C3A—C12A—C13A | 6.2 (4) | C4B—C3B—C12B—C13B | 36.8 (3) |
N2A—C3A—C12A—C17A | 2.4 (4) | N2B—C3B—C12B—C17B | 32.1 (3) |
C4A—C3A—C12A—C17A | −176.5 (2) | C4B—C3B—C12B—C17B | −140.8 (2) |
C17A—C12A—C13A—C14A | −1.6 (4) | C17B—C12B—C13B—C14B | −1.5 (3) |
C3A—C12A—C13A—C14A | 175.8 (2) | C3B—C12B—C13B—C14B | −179.1 (2) |
C12A—C13A—C14A—C15A | 0.7 (4) | C12B—C13B—C14B—C15B | 1.1 (4) |
C13A—C14A—C15A—C16A | 0.7 (4) | C13B—C14B—C15B—C16B | 0.7 (4) |
C13A—C14A—C15A—Cl2A | −178.9 (2) | C13B—C14B—C15B—Cl1B | 179.95 (18) |
C14A—C15A—C16A—C17A | −1.2 (4) | C14B—C15B—C16B—C17B | −2.1 (4) |
Cl2A—C15A—C16A—C17A | 178.4 (2) | Cl1B—C15B—C16B—C17B | 178.7 (2) |
C15A—C16A—C17A—C12A | 0.3 (4) | C15B—C16B—C17B—C12B | 1.7 (4) |
C13A—C12A—C17A—C16A | 1.1 (4) | C13B—C12B—C17B—C16B | 0.1 (4) |
C3A—C12A—C17A—C16A | −176.4 (2) | C3B—C12B—C17B—C16B | 177.7 (2) |
O1'A—C6'A—C18A—C19A | 179.9 (3) | O1'B—C6'B—C18B—C19B | 178.8 (3) |
C5'A—C6'A—C18A—C19A | 1.3 (4) | C5'B—C6'B—C18B—C19B | 0.1 (4) |
C6'A—C18A—C19A—C20A | −0.2 (5) | C6'B—C18B—C19B—C20B | 1.4 (5) |
C18A—C19A—C20A—C21A | 0.3 (5) | C18B—C19B—C20B—C21B | −1.6 (5) |
C19A—C20A—C21A—C5'A | −1.5 (5) | C19B—C20B—C21B—C5'B | 0.3 (4) |
C6'A—C5'A—C21A—C20A | 2.6 (4) | C6'B—C5'B—C21B—C20B | 1.2 (4) |
C4'A—C5'A—C21A—C20A | −174.1 (3) | C4'B—C5'B—C21B—C20B | −176.5 (2) |
O1'A—C2'A—C22A—C27A | 102.5 (3) | O1'B—C2'B—C22B—C27B | 93.7 (2) |
C5A—C2'A—C22A—C27A | −23.7 (4) | C5B—C2'B—C22B—C27B | −33.1 (3) |
O1'A—C2'A—C22A—C23A | −76.4 (3) | O1'B—C2'B—C22B—C23B | −86.9 (2) |
C5A—C2'A—C22A—C23A | 157.4 (3) | C5B—C2'B—C22B—C23B | 146.3 (2) |
C27A—C22A—C23A—C24A | 0.3 (5) | C27B—C22B—C23B—C24B | 0.7 (4) |
C2'A—C22A—C23A—C24A | 179.3 (3) | C2'B—C22B—C23B—C24B | −178.8 (3) |
C22A—C23A—C24A—C25A | −1.4 (7) | C22B—C23B—C24B—C25B | −1.7 (5) |
C23A—C24A—C25A—C26A | 1.7 (7) | C23B—C24B—C25B—C26B | 0.9 (4) |
C24A—C25A—C26A—C27A | −1.0 (6) | C24B—C25B—C26B—C27B | 0.8 (2) |
C23A—C22A—C27A—C26A | 0.5 (5) | C25B—C26B—C27B—C22B | −1.8 (3) |
C2'A—C22A—C27A—C26A | −178.5 (3) | C23B—C22B—C27B—C26B | 1.0 (4) |
C25A—C26A—C27A—C22A | −0.1 (6) | C2'B—C22B—C27B—C26B | −179.6 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4A—H4A···O7′A | 0.98 | 2.42 | 2.792 (3) | 102 |
C10A—H10A···N2B | 0.93 | 2.67 | 3.417 (3) | 138 |
C27A—H27A···O7′A | 0.93 | 2.75 | 3.595 (3) | 151 |
C11A—H11A···O7′Ai | 0.93 | 2.72 | 3.570 (3) | 152 |
C4A—H4A···O7′Ai | 0.98 | 2.68 | 3.619 (3) | 161 |
C17A—H17A···O1Aii | 0.93 | 2.67 | 3.550 (3) | 158 |
C4B—H4B···O7′Biii | 0.98 | 2.57 | 3.531 (3) | 167 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x−1, −y+2, −z; (iii) −x+1, −y+2, −z+1. |
Experimental details
Crystal data |
Chemical formula | C29H19Cl2NO3 |
Mr | 500.35 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 11.2032 (10), 12.349 (2), 18.973 (5) |
α, β, γ (°) | 108.89 (1), 105.09 (1), 91.66 (1) |
V (Å3) | 2379.5 (8) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 2.72 |
Crystal size (mm) | 0.3 × 0.25 × 0.10 |
|
Data collection |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.638, 0.762 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9478, 9032, 6262 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.139, 1.02 |
No. of reflections | 9032 |
No. of parameters | 629 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.36 |
Selected geometric parameters (Å, º) topCl1A—C9A | 1.735 (2) | Cl1B—C15B | 1.730 (3) |
Cl2A—C15A | 1.735 (3) | Cl2B—C9B | 1.741 (2) |
O1'A—C6'A | 1.354 (3) | O1'B—C6'B | 1.359 (2) |
O1'A—C2'A | 1.456 (3) | O1'B—C2'B | 1.448 (3) |
C2'A—C5A | 1.509 (3) | C2'B—C22B | 1.506 (3) |
C4'A—O7'A | 1.218 (3) | C2'B—C5B | 1.524 (3) |
C4'A—C5A | 1.531 (3) | C4'B—O7'B | 1.214 (2) |
C5'A—C6'A | 1.394 (3) | C4'B—C5B | 1.533 (3) |
O1A—N2A | 1.412 (3) | C5'B—C6'B | 1.397 (3) |
O1A—C5A | 1.463 (3) | O1B—C5B | 1.465 (3) |
N2A—C3A | 1.275 (3) | N2B—C3B | 1.278 (3) |
C3A—C4A | 1.508 (3) | C3B—C4B | 1.505 (3) |
C4A—C5A | 1.536 (3) | C4B—C5B | 1.535 (3) |
| | | |
C5A—O1A—N2A—C3A | −13.4 (3) | C5B—O1B—N2B—C3B | −13.1 (2) |
O1A—N2A—C3A—C4A | −2.3 (3) | O1B—N2B—C3B—C4B | −1.1 (2) |
N2A—C3A—C4A—C5A | 15.8 (3) | N2B—C3B—C4B—C5B | 13.7 (2) |
N2A—O1A—C5A—C4A | 22.7 (2) | N2B—O1B—C5B—C4B | 21.11 (19) |
C3A—C4A—C5A—O1A | −21.9 (2) | C3B—C4B—C5B—O1B | −19.88 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4A—H4A···O7'A | 0.98 | 2.42 | 2.792 (3) | 102 |
C10A—H10A···N2B | 0.93 | 2.67 | 3.417 (3) | 138 |
C27A—H27A···O7'A | 0.93 | 2.75 | 3.595 (3) | 151 |
C11A—H11A···O7'Ai | 0.93 | 2.72 | 3.570 (3) | 152 |
C4A—H4A···O7'Ai | 0.98 | 2.68 | 3.619 (3) | 161 |
C17A—H17A···O1Aii | 0.93 | 2.67 | 3.550 (3) | 158 |
C4B—H4B···O7'Biii | 0.98 | 2.57 | 3.531 (3) | 167 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x−1, −y+2, −z; (iii) −x+1, −y+2, −z+1. |
Flavonones are widely distributed and they form a part of our human diet, owing to their abundance in edible plants. The vitality of these compounds is confirmed by their pharmacological activities. They possess therapeutic properties such as antiviral, antibiotic and antitumour (Cody, 1988). Spiroisoxazolines display interesting biological properties, such as herbicidal, plant-growth regulatory and antitumour activities (Howe & Shelton, 1990; Smietana et al., 1999). To understand the structure and conformation, a crystallographic study of the title compound, (I), was undertaken.
The bond geometry of the flavanone moiety in (I) agrees with reported values (Tomlin & Cantrell, 1990). As shown in Fig. 1, the pyran ring is planar, with the fused phenyl ring making the dihedral angle of 3.5 (1)° in molecule A and 3.2 (1)° in molecule B, which are larger than the reported value (Kendi & Ozbey, 1995). This may be due to the substitution at C5. The best plane of the benzopyran ring is perpendicular to the isoxazoline ring plane. Conformational parameters (Cremer & Pople, 1975) for the pyran ring are q2 = 0.360 (3) Å, q3 = −0.261 (3) Å QT = 0.445 (2) Å and ϕ2 = −91.8 (4)° in molecule A; q2 = 0.341 (3) Å, q3 = −0.260 (2) Å, QT = 0.428 (2) Å and ϕ2 = −95.6 (4)° in molecule B. For the isoxazoline ring, q2 = 0.231 (2) Å and ϕ2 = −41.0 (6)° in molecule A; q2 = 0.211 (2) Å and ϕ2 = −38.8 (6)° in molecule B, which confirm their envelope conformations. Apart from van der Waals interactions, the packing of the molecules in the crystal lattice is stabilized by intermolecular C—H···O and C—H···N interactions (Table 2).