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The title compound, C29H19Cl2NO3, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803001387/ob6202sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803001387/ob6202Isup2.hkl
Contains datablock I

CCDC reference: 154651

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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


Yellow Alert 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

Comment top

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).

Experimental top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I), showing ellipsoids at the 40% probability level for non-H atoms.
Spiro[3,4-di(4-chlorophenyl)-4,5-dihydroisoxazole-5,3'-flavan-4'-one] top
Crystal data top
C29H19Cl2NO3Z = 4
Mr = 500.35F(000) = 1032
Triclinic, P1Dx = 1.397 Mg m3
a = 11.2032 (10) ÅCu Kα radiation, λ = 1.5418 Å
b = 12.349 (2) ÅCell parameters from 25 reflections
c = 18.973 (5) Åθ = 14–25°
α = 108.89 (1)°µ = 2.72 mm1
β = 105.09 (1)°T = 293 K
γ = 91.66 (1)°Needle, colourless
V = 2379.5 (8) Å30.3 × 0.25 × 0.10 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
6262 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.047
Graphite monochromatorθmax = 72.0°, θmin = 2.6°
ω–2θ scansh = 1313
Absorption correction: ψ scan
(North et al., 1968)
k = 015
Tmin = 0.638, Tmax = 0.762l = 2322
9478 measured reflections3 standard reflections every 200 reflections
9032 independent reflections intensity decay: <0.1%
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)] = 0.044H-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 reflectionsΔρmax = 0.26 e Å3
629 parametersΔρmin = 0.36 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0021 (2)
Crystal data top
C29H19Cl2NO3γ = 91.66 (1)°
Mr = 500.35V = 2379.5 (8) Å3
Triclinic, P1Z = 4
a = 11.2032 (10) ÅCu Kα radiation
b = 12.349 (2) ŵ = 2.72 mm1
c = 18.973 (5) ÅT = 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 = 0.7623 standard reflections every 200 reflections
9478 measured reflections intensity decay: <0.1%
9032 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.139H-atom parameters constrained
S = 1.02Δρmax = 0.26 e Å3
9032 reflectionsΔρmin = 0.36 e Å3
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
xyzUiso*/Ueq
Cl1A0.03398 (7)0.94750 (6)0.40389 (4)0.0765 (2)
Cl2A0.19490 (9)1.55588 (7)0.20412 (5)0.0978 (3)
O1'A0.28032 (15)0.64837 (15)0.03368 (9)0.0655 (4)
C2'A0.1957 (2)0.7420 (2)0.02954 (13)0.0582 (6)
H2'A0.21970.74780.07660.070*
C4'A0.2010 (2)0.8493 (2)0.06300 (14)0.0604 (6)
C5'A0.2554 (2)0.7401 (2)0.12504 (14)0.0604 (6)
C6'A0.2956 (2)0.6469 (2)0.10716 (14)0.0583 (6)
O7'A0.15443 (19)0.93177 (17)0.07273 (11)0.0791 (5)
O1A0.34627 (14)0.86759 (16)0.00810 (11)0.0730 (5)
N2A0.35683 (19)0.9864 (2)0.03769 (14)0.0752 (6)
C3A0.2492 (2)1.0418 (2)0.07613 (14)0.0598 (6)
C4A0.14575 (19)0.9667 (2)0.08157 (13)0.0555 (5)
H4A0.07650.99670.06770.067*
C5A0.2143 (2)0.8552 (2)0.01638 (13)0.0563 (5)
C6A0.10049 (19)0.9611 (2)0.16245 (13)0.0536 (5)
C7A0.1838 (2)0.9435 (2)0.20150 (14)0.0635 (6)
H7A0.26890.93580.17760.076*
C8A0.1435 (2)0.9373 (2)0.27481 (14)0.0647 (6)
H8A0.20040.92340.29990.078*
C9A0.0175 (2)0.9518 (2)0.31041 (14)0.0578 (6)
C10A0.0675 (2)0.9716 (2)0.27416 (15)0.0620 (6)
H10A0.15250.98230.29920.074*
C11A0.0256 (2)0.9753 (2)0.20000 (14)0.0592 (6)
H11A0.08290.98760.17480.071*
C12A0.2350 (2)1.1679 (2)0.11149 (14)0.0610 (6)
C13A0.1187 (2)1.2313 (2)0.14837 (15)0.0670 (6)
H13A0.04821.19330.15390.080*
C14A0.1061 (3)1.3509 (2)0.17721 (15)0.0717 (7)
H14A0.02761.39310.20140.086*
C15A0.2100 (3)1.4063 (2)0.16975 (15)0.0704 (7)
C16A0.3271 (3)1.3455 (3)0.13483 (17)0.0789 (8)
H16A0.39731.38420.13090.095*
C17A0.3393 (2)1.2269 (3)0.10573 (16)0.0733 (7)
H17A0.41831.18550.08190.088*
C18A0.3573 (3)0.5463 (2)0.16613 (16)0.0707 (7)
H18A0.38560.48470.15420.085*
C19A0.3766 (3)0.5382 (3)0.24236 (17)0.0858 (9)
H19A0.41780.47060.28190.103*
C20A0.3358 (4)0.6283 (3)0.26063 (17)0.0956 (11)
H20A0.34980.62170.31250.115*
C21A0.2743 (3)0.7284 (3)0.20305 (16)0.0778 (8)
H21A0.24520.78870.21590.093*
C22A0.0651 (2)0.7112 (2)0.04279 (13)0.0578 (6)
C23A0.0339 (3)0.6341 (3)0.0813 (2)0.0923 (10)
H23A0.09360.60430.09840.111*
C24A0.0833 (4)0.6002 (4)0.0951 (3)0.1137 (13)
H24A0.10260.54940.12230.136*
C25A0.1712 (3)0.6415 (3)0.0689 (2)0.0958 (10)
H25A0.25000.61740.07680.115*
C26A0.1426 (3)0.7173 (3)0.0316 (2)0.0918 (10)
H26A0.20260.74640.01430.110*
C27A0.0261 (2)0.7522 (3)0.01848 (18)0.0782 (8)
H27A0.00860.80480.00740.094*
Cl1B0.52718 (8)0.64612 (7)0.07550 (5)0.0982 (3)
Cl2B1.02062 (8)1.29857 (9)0.37424 (6)0.1102 (3)
O1'B0.44224 (16)1.39783 (13)0.51642 (11)0.0658 (5)
C2'B0.5288 (2)1.32046 (18)0.49036 (14)0.0537 (5)
H2'B0.56191.34980.45610.064*
C4'B0.3844 (2)1.15374 (18)0.48322 (13)0.0498 (5)
C5'B0.3253 (2)1.24131 (18)0.53039 (13)0.0499 (5)
C6'B0.3554 (2)1.35809 (19)0.54351 (14)0.0546 (5)
O7'B0.36989 (15)1.05176 (13)0.47398 (10)0.0620 (4)
O1B0.36655 (15)1.21113 (14)0.37540 (10)0.0608 (4)
N2B0.35608 (18)1.11148 (18)0.30973 (12)0.0600 (5)
C3B0.4486 (2)1.05591 (19)0.32394 (13)0.0513 (5)
C4B0.54038 (19)1.11146 (18)0.40293 (12)0.0480 (5)
H4B0.55691.05510.42950.058*
C5B0.4621 (2)1.19983 (18)0.44106 (13)0.0489 (5)
C6B0.66080 (19)1.15896 (17)0.39506 (12)0.0476 (5)
C7B0.6600 (2)1.20930 (19)0.33940 (13)0.0546 (5)
H7B0.58451.21380.30610.065*
C8B0.7702 (2)1.2530 (2)0.33269 (15)0.0633 (6)
H8B0.76921.28650.29520.076*
C9B0.8808 (2)1.2460 (2)0.38236 (16)0.0664 (7)
C10B0.8840 (2)1.1966 (2)0.43766 (16)0.0661 (6)
H10B0.95971.19310.47110.079*
C11B0.7734 (2)1.1519 (2)0.44335 (13)0.0566 (5)
H11B0.77531.11680.48010.068*
C12B0.4666 (2)0.9537 (2)0.26283 (13)0.0545 (5)
C13B0.5244 (2)0.8653 (2)0.28150 (15)0.0610 (6)
H13B0.55130.86980.33320.073*
C14B0.5426 (2)0.7701 (2)0.22387 (16)0.0686 (7)
H14B0.58030.71020.23660.082*
C15B0.5048 (2)0.7647 (2)0.14796 (16)0.0692 (7)
C16B0.4506 (3)0.8525 (3)0.12843 (16)0.0772 (8)
H16B0.42770.84910.07690.093*
C17B0.4298 (3)0.9466 (2)0.18562 (15)0.0709 (7)
H17B0.39091.00550.17220.085*
C18B0.2950 (3)1.4409 (2)0.58431 (16)0.0699 (7)
H18B0.31561.51840.59260.084*
C19B0.2042 (3)1.4079 (2)0.61257 (16)0.0737 (7)
H19B0.16211.46340.63910.088*
C20B0.1747 (3)1.2927 (2)0.60186 (15)0.0708 (7)
H20B0.11461.27130.62230.085*
C21B0.2343 (2)1.2110 (2)0.56130 (13)0.0575 (6)
H21B0.21401.13380.55410.069*
C22B0.6382 (2)1.32612 (18)0.55793 (13)0.0538 (5)
C23B0.7385 (3)1.4093 (2)0.57932 (17)0.0733 (7)
H23B0.73611.46070.55260.088*
C24B0.8418 (3)1.4171 (3)0.63952 (19)0.0920 (10)
H24B0.90931.47240.65220.110*
C25B0.8461 (2)1.34455 (19)0.68079 (12)0.0884 (9)
H25B0.91571.35080.72200.106*
C26B0.7469 (2)1.26223 (19)0.66103 (12)0.0780 (8)
H26B0.74881.21300.68940.094*
C27B0.6443 (2)1.2520 (2)0.59938 (15)0.0637 (6)
H27B0.57851.19440.58560.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0803 (4)0.0854 (5)0.0584 (4)0.0008 (3)0.0091 (3)0.0268 (3)
Cl2A0.1323 (7)0.0787 (5)0.0910 (5)0.0209 (5)0.0514 (5)0.0242 (4)
O1'A0.0613 (10)0.0745 (11)0.0558 (9)0.0150 (8)0.0125 (8)0.0211 (8)
C2'A0.0510 (12)0.0709 (15)0.0509 (12)0.0086 (10)0.0141 (10)0.0202 (11)
C4'A0.0557 (13)0.0683 (15)0.0585 (14)0.0032 (11)0.0120 (11)0.0273 (12)
C5'A0.0655 (14)0.0619 (14)0.0545 (13)0.0115 (11)0.0151 (11)0.0220 (11)
C6'A0.0536 (13)0.0667 (14)0.0527 (13)0.0069 (11)0.0113 (10)0.0213 (11)
O7'A0.0930 (14)0.0791 (12)0.0644 (11)0.0110 (10)0.0127 (10)0.0330 (9)
O1A0.0399 (8)0.0818 (12)0.0788 (12)0.0021 (8)0.0090 (8)0.0103 (9)
N2A0.0442 (11)0.0857 (16)0.0778 (15)0.0066 (10)0.0049 (10)0.0143 (12)
C3A0.0456 (12)0.0726 (15)0.0555 (13)0.0041 (11)0.0097 (10)0.0186 (11)
C4A0.0390 (11)0.0698 (14)0.0546 (13)0.0015 (10)0.0104 (10)0.0201 (11)
C5A0.0397 (11)0.0702 (14)0.0560 (13)0.0010 (10)0.0121 (10)0.0195 (11)
C6A0.0385 (10)0.0646 (13)0.0527 (12)0.0035 (9)0.0099 (9)0.0167 (10)
C7A0.0370 (11)0.0890 (18)0.0577 (14)0.0050 (11)0.0111 (10)0.0194 (12)
C8A0.0488 (13)0.0859 (17)0.0542 (13)0.0074 (11)0.0167 (11)0.0171 (12)
C9A0.0540 (13)0.0575 (13)0.0555 (13)0.0044 (10)0.0097 (10)0.0165 (10)
C10A0.0393 (11)0.0747 (15)0.0669 (15)0.0062 (10)0.0032 (10)0.0283 (12)
C11A0.0400 (11)0.0734 (15)0.0672 (15)0.0036 (10)0.0153 (11)0.0288 (12)
C12A0.0514 (13)0.0763 (16)0.0509 (13)0.0082 (11)0.0114 (10)0.0187 (11)
C13A0.0559 (14)0.0764 (17)0.0618 (15)0.0081 (12)0.0102 (12)0.0198 (13)
C14A0.0708 (17)0.0751 (17)0.0617 (15)0.0018 (13)0.0158 (13)0.0168 (13)
C15A0.0855 (19)0.0736 (17)0.0546 (14)0.0148 (14)0.0271 (14)0.0192 (12)
C16A0.0708 (18)0.095 (2)0.0783 (19)0.0294 (16)0.0301 (15)0.0307 (16)
C17A0.0554 (14)0.0877 (19)0.0735 (17)0.0121 (13)0.0190 (13)0.0226 (14)
C18A0.0743 (17)0.0605 (15)0.0687 (16)0.0081 (12)0.0102 (13)0.0187 (12)
C19A0.114 (2)0.0631 (17)0.0601 (16)0.0200 (16)0.0051 (16)0.0092 (13)
C20A0.150 (3)0.0754 (19)0.0542 (16)0.036 (2)0.0169 (18)0.0205 (14)
C21A0.106 (2)0.0720 (17)0.0578 (15)0.0205 (15)0.0194 (15)0.0278 (13)
C22A0.0546 (13)0.0693 (14)0.0511 (12)0.0026 (11)0.0133 (10)0.0249 (11)
C23A0.082 (2)0.109 (2)0.120 (3)0.0121 (18)0.0401 (19)0.075 (2)
C24A0.092 (2)0.137 (3)0.155 (4)0.035 (2)0.037 (2)0.103 (3)
C25A0.0668 (19)0.118 (3)0.120 (3)0.0221 (18)0.0233 (18)0.064 (2)
C26A0.0566 (16)0.134 (3)0.111 (2)0.0150 (17)0.0249 (16)0.076 (2)
C27A0.0552 (15)0.108 (2)0.098 (2)0.0111 (14)0.0253 (14)0.0672 (18)
Cl1B0.0988 (6)0.0930 (5)0.0856 (5)0.0106 (4)0.0461 (4)0.0057 (4)
Cl2B0.0697 (5)0.1307 (7)0.1327 (7)0.0221 (5)0.0418 (5)0.0414 (6)
O1'B0.0727 (11)0.0487 (8)0.0993 (13)0.0145 (7)0.0484 (10)0.0365 (9)
C2'B0.0578 (13)0.0463 (11)0.0695 (14)0.0065 (9)0.0323 (11)0.0254 (10)
C4'B0.0468 (11)0.0470 (11)0.0582 (13)0.0007 (9)0.0149 (10)0.0221 (10)
C5'B0.0498 (12)0.0499 (11)0.0524 (12)0.0018 (9)0.0163 (10)0.0198 (9)
C6'B0.0584 (13)0.0507 (12)0.0642 (14)0.0057 (10)0.0261 (11)0.0256 (10)
O7'B0.0653 (10)0.0466 (8)0.0851 (12)0.0036 (7)0.0335 (9)0.0281 (8)
O1B0.0599 (9)0.0670 (10)0.0643 (10)0.0172 (8)0.0175 (8)0.0336 (8)
N2B0.0537 (11)0.0693 (12)0.0599 (12)0.0022 (9)0.0150 (9)0.0277 (10)
C3B0.0472 (12)0.0561 (12)0.0537 (12)0.0016 (9)0.0132 (10)0.0244 (10)
C4B0.0468 (11)0.0479 (11)0.0521 (12)0.0026 (9)0.0148 (9)0.0206 (9)
C5B0.0489 (11)0.0489 (11)0.0557 (12)0.0046 (9)0.0162 (10)0.0260 (10)
C6B0.0473 (11)0.0459 (11)0.0487 (11)0.0023 (8)0.0155 (9)0.0139 (9)
C7B0.0522 (12)0.0584 (13)0.0562 (13)0.0028 (10)0.0148 (10)0.0245 (10)
C8B0.0678 (16)0.0622 (14)0.0667 (15)0.0017 (11)0.0284 (13)0.0248 (12)
C9B0.0573 (14)0.0637 (15)0.0742 (16)0.0062 (11)0.0276 (13)0.0126 (12)
C10B0.0460 (12)0.0748 (16)0.0692 (16)0.0044 (11)0.0119 (11)0.0176 (13)
C11B0.0505 (12)0.0626 (13)0.0549 (13)0.0064 (10)0.0141 (10)0.0183 (11)
C12B0.0473 (12)0.0585 (13)0.0538 (12)0.0097 (10)0.0128 (10)0.0167 (10)
C13B0.0621 (14)0.0626 (14)0.0586 (14)0.0001 (11)0.0195 (11)0.0201 (11)
C14B0.0652 (15)0.0626 (15)0.0771 (17)0.0004 (12)0.0275 (13)0.0177 (13)
C15B0.0594 (14)0.0701 (16)0.0667 (16)0.0165 (12)0.0262 (12)0.0043 (13)
C16B0.0767 (18)0.088 (2)0.0525 (14)0.0116 (15)0.0119 (13)0.0119 (14)
C17B0.0721 (16)0.0764 (17)0.0564 (15)0.0017 (13)0.0090 (13)0.0207 (13)
C18B0.0836 (18)0.0530 (13)0.0837 (18)0.0107 (12)0.0415 (15)0.0233 (12)
C19B0.0841 (18)0.0669 (16)0.0787 (18)0.0120 (13)0.0471 (15)0.0172 (13)
C20B0.0732 (16)0.0718 (16)0.0700 (16)0.0035 (13)0.0381 (14)0.0147 (13)
C21B0.0565 (13)0.0574 (13)0.0577 (13)0.0064 (10)0.0205 (11)0.0164 (10)
C22B0.0573 (13)0.0436 (11)0.0610 (13)0.0016 (9)0.0259 (11)0.0118 (10)
C23B0.0801 (18)0.0592 (15)0.0745 (17)0.0136 (13)0.0273 (15)0.0126 (13)
C24B0.081 (2)0.089 (2)0.084 (2)0.0270 (17)0.0154 (17)0.0101 (17)
C25B0.0687 (18)0.094 (2)0.077 (2)0.0001 (16)0.0057 (15)0.0074 (17)
C26B0.0759 (18)0.0768 (18)0.0783 (19)0.0081 (14)0.0145 (15)0.0286 (15)
C27B0.0599 (14)0.0588 (14)0.0717 (16)0.0012 (11)0.0156 (12)0.0245 (12)
Geometric parameters (Å, º) top
Cl1A—C9A1.735 (2)Cl1B—C15B1.730 (3)
Cl2A—C15A1.735 (3)Cl2B—C9B1.741 (2)
O1'A—C6'A1.354 (3)O1'B—C6'B1.359 (2)
O1'A—C2'A1.456 (3)O1'B—C2'B1.448 (3)
C2'A—C22A1.501 (3)C2'B—C22B1.506 (3)
C2'A—C5A1.509 (3)C2'B—C5B1.524 (3)
C2'A—H2'A0.9800C2'B—H2'B0.9800
C4'A—O7'A1.218 (3)C4'B—O7'B1.214 (2)
C4'A—C5'A1.459 (3)C4'B—C5'B1.460 (3)
C4'A—C5A1.531 (3)C4'B—C5B1.533 (3)
C5'A—C6'A1.394 (3)C5'B—C21B1.399 (3)
C5'A—C21A1.397 (3)C5'B—C6'B1.397 (3)
C6'A—C18A1.386 (3)C6'B—C18B1.380 (3)
O1A—N2A1.412 (3)O1B—N2B1.415 (3)
O1A—C5A1.463 (3)O1B—C5B1.465 (3)
N2A—C3A1.275 (3)N2B—C3B1.278 (3)
C3A—C12A1.467 (3)C3B—C12B1.472 (3)
C3A—C4A1.508 (3)C3B—C4B1.505 (3)
C4A—C6A1.511 (3)C4B—C6B1.517 (3)
C4A—C5A1.536 (3)C4B—C5B1.535 (3)
C4A—H4A0.9800C4B—H4B0.9800
C6A—C11A1.383 (3)C6B—C11B1.377 (3)
C6A—C7A1.386 (3)C6B—C7B1.386 (3)
C7A—C8A1.374 (3)C7B—C8B1.386 (3)
C7A—H7A0.9300C7B—H7B0.9300
C8A—C9A1.375 (3)C8B—C9B1.372 (4)
C8A—H8A0.9300C8B—H8B0.9300
C9A—C10A1.370 (3)C9B—C10B1.367 (4)
C10A—C11A1.379 (3)C10B—C11B1.385 (3)
C10A—H10A0.9300C10B—H10B0.9300
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.383 (3)C12B—C13B1.382 (3)
C12A—C17A1.393 (4)C12B—C17B1.387 (3)
C13A—C14A1.388 (4)C13B—C14B1.384 (3)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.366 (4)C14B—C15B1.370 (4)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.375 (4)C15B—C16B1.365 (4)
C16A—C17A1.377 (4)C16B—C17B1.383 (4)
C16A—H16A0.9300C16B—H16B0.9300
C17A—H17A0.9300C17B—H17B0.9300
C18A—C19A1.375 (4)C18B—C19B1.375 (3)
C18A—H18A0.9300C18B—H18B0.9300
C19A—C20A1.368 (5)C19B—C20B1.388 (4)
C19A—H19A0.9300C19B—H19B0.9300
C20A—C21A1.371 (4)C20B—C21B1.364 (3)
C20A—H20A0.9300C20B—H20B0.9300
C21A—H21A0.9300C21B—H21B0.9300
C22A—C27A1.371 (3)C22B—C27B1.380 (3)
C22A—C23A1.377 (4)C22B—C23B1.381 (3)
C23A—C24A1.375 (5)C23B—C24B1.373 (4)
C23A—H23A0.9300C23B—H23B0.9300
C24A—C25A1.367 (5)C24B—C25B1.362 (4)
C24A—H24A0.9300C24B—H24B0.9300
C25A—C26A1.345 (4)C25B—C26B1.3710
C25A—H25A0.9300C25B—H25B0.9300
C26A—C27A1.373 (4)C26B—C27B1.379 (3)
C26A—H26A0.9300C26B—H26B0.9300
C27A—H27A0.9300C27B—H27B0.9300
C6'A—O1'A—C2'A117.90 (17)C6'B—O1'B—C2'B117.77 (16)
O1'A—C2'A—C22A109.9 (2)O1'B—C2'B—C22B110.43 (18)
O1'A—C2'A—C5A110.38 (19)O1'B—C2'B—C5B111.10 (18)
C22A—C2'A—C5A116.16 (18)C22B—C2'B—C5B115.20 (18)
O1'A—C2'A—H2'A106.6O1'B—C2'B—H2'B106.5
C22A—C2'A—H2'A106.6C22B—C2'B—H2'B106.5
C5A—C2'A—H2'A106.6C5B—C2'B—H2'B106.5
O7'A—C4'A—C5'A124.2 (2)O7'B—C4'B—C5'B124.19 (19)
O7'A—C4'A—C5A121.8 (2)O7'B—C4'B—C5B121.48 (19)
C5'A—C4'A—C5A113.9 (2)C5'B—C4'B—C5B114.23 (17)
C6'A—C5'A—C21A118.8 (2)C21B—C5'B—C6'B118.1 (2)
C6'A—C5'A—C4'A119.9 (2)C21B—C5'B—C4'B121.34 (19)
C21A—C5'A—C4'A121.1 (2)C6'B—C5'B—C4'B120.52 (19)
O1'A—C6'A—C18A116.1 (2)O1'B—C6'B—C18B115.7 (2)
O1'A—C6'A—C5'A123.7 (2)O1'B—C6'B—C5'B123.4 (2)
C18A—C6'A—C5'A120.2 (2)C18B—C6'B—C5'B120.9 (2)
N2A—O1A—C5A107.82 (16)N2B—O1B—C5B108.07 (16)
C3A—N2A—O1A109.4 (2)C3B—N2B—O1B109.26 (18)
N2A—C3A—C12A119.8 (2)N2B—C3B—C12B120.5 (2)
N2A—C3A—C4A114.3 (2)N2B—C3B—C4B114.4 (2)
C12A—C3A—C4A125.9 (2)C12B—C3B—C4B124.7 (2)
C3A—C4A—C6A110.89 (19)C3B—C4B—C6B110.06 (17)
C3A—C4A—C5A98.77 (18)C3B—C4B—C5B99.35 (17)
C6A—C4A—C5A116.8 (2)C6B—C4B—C5B116.82 (17)
C3A—C4A—H4A109.9C3B—C4B—H4B110.0
C6A—C4A—H4A109.9C6B—C4B—H4B110.0
C5A—C4A—H4A109.9C5B—C4B—H4B110.0
O1A—C5A—C2'A105.81 (18)O1B—C5B—C2'B107.00 (17)
O1A—C5A—C4'A102.94 (18)O1B—C5B—C4'B102.43 (16)
C2'A—C5A—C4'A111.3 (2)C2'B—C5B—C4'B111.53 (18)
O1A—C5A—C4A104.12 (18)O1B—C5B—C4B104.21 (17)
C2'A—C5A—C4A118.4 (2)C2'B—C5B—C4B116.80 (17)
C4'A—C5A—C4A112.48 (19)C4'B—C5B—C4B113.30 (17)
C11A—C6A—C7A118.2 (2)C11B—C6B—C7B118.9 (2)
C11A—C6A—C4A120.73 (19)C11B—C6B—C4B120.03 (19)
C7A—C6A—C4A121.0 (2)C7B—C6B—C4B121.11 (19)
C8A—C7A—C6A121.4 (2)C8B—C7B—C6B120.9 (2)
C8A—C7A—H7A119.3C8B—C7B—H7B119.6
C6A—C7A—H7A119.3C6B—C7B—H7B119.6
C7A—C8A—C9A118.8 (2)C9B—C8B—C7B118.8 (2)
C7A—C8A—H8A120.6C9B—C8B—H8B120.6
C9A—C8A—H8A120.6C7B—C8B—H8B120.6
C10A—C9A—C8A121.4 (2)C10B—C9B—C8B121.4 (2)
C10A—C9A—Cl1A119.59 (18)C10B—C9B—Cl2B118.9 (2)
C8A—C9A—Cl1A119.03 (19)C8B—C9B—Cl2B119.7 (2)
C9A—C10A—C11A119.1 (2)C9B—C10B—C11B119.4 (2)
C9A—C10A—H10A120.4C9B—C10B—H10B120.3
C11A—C10A—H10A120.4C11B—C10B—H10B120.3
C10A—C11A—C6A121.1 (2)C6B—C11B—C10B120.6 (2)
C10A—C11A—H11A119.5C6B—C11B—H11B119.7
C6A—C11A—H11A119.5C10B—C11B—H11B119.7
C13A—C12A—C17A118.4 (3)C13B—C12B—C17B118.8 (2)
C13A—C12A—C3A121.2 (2)C13B—C12B—C3B120.7 (2)
C17A—C12A—C3A120.3 (2)C17B—C12B—C3B120.4 (2)
C12A—C13A—C14A120.7 (3)C12B—C13B—C14B120.5 (2)
C12A—C13A—H13A119.7C12B—C13B—H13B119.8
C14A—C13A—H13A119.7C14B—C13B—H13B119.8
C15A—C14A—C13A119.5 (3)C15B—C14B—C13B119.6 (3)
C15A—C14A—H14A120.2C15B—C14B—H14B120.2
C13A—C14A—H14A120.2C13B—C14B—H14B120.2
C14A—C15A—C16A121.1 (3)C16B—C15B—C14B120.9 (3)
C14A—C15A—Cl2A119.8 (2)C16B—C15B—Cl1B119.1 (2)
C16A—C15A—Cl2A119.1 (2)C14B—C15B—Cl1B120.0 (2)
C15A—C16A—C17A119.3 (3)C15B—C16B—C17B119.7 (3)
C15A—C16A—H16A120.4C15B—C16B—H16B120.2
C17A—C16A—H16A120.4C17B—C16B—H16B120.2
C16A—C17A—C12A121.0 (3)C16B—C17B—C12B120.5 (3)
C16A—C17A—H17A119.5C16B—C17B—H17B119.8
C12A—C17A—H17A119.5C12B—C17B—H17B119.8
C19A—C18A—C6'A119.6 (3)C19B—C18B—C6'B119.5 (2)
C19A—C18A—H18A120.2C19B—C18B—H18B120.3
C6'A—C18A—H18A120.2C6'B—C18B—H18B120.3
C20A—C19A—C18A120.8 (3)C18B—C19B—C20B120.7 (2)
C20A—C19A—H19A119.6C18B—C19B—H19B119.7
C18A—C19A—H19A119.6C20B—C19B—H19B119.7
C19A—C20A—C21A120.5 (3)C21B—C20B—C19B119.7 (2)
C19A—C20A—H20A119.8C21B—C20B—H20B120.1
C21A—C20A—H20A119.8C19B—C20B—H20B120.1
C20A—C21A—C5'A120.1 (3)C20B—C21B—C5'B121.1 (2)
C20A—C21A—H21A119.9C20B—C21B—H21B119.5
C5'A—C21A—H21A119.9C5'B—C21B—H21B119.5
C27A—C22A—C23A116.9 (2)C27B—C22B—C23B118.0 (2)
C27A—C22A—C2'A125.2 (2)C27B—C22B—C2'B123.6 (2)
C23A—C22A—C2'A117.9 (2)C23B—C22B—C2'B118.4 (2)
C24A—C23A—C22A121.8 (3)C24B—C23B—C22B121.0 (3)
C24A—C23A—H23A119.1C24B—C23B—H23B119.5
C22A—C23A—H23A119.1C22B—C23B—H23B119.5
C25A—C24A—C23A119.7 (3)C25B—C24B—C23B120.5 (3)
C25A—C24A—H24A120.1C25B—C24B—H24B119.7
C23A—C24A—H24A120.1C23B—C24B—H24B119.7
C26A—C25A—C24A119.3 (3)C24B—C25B—C26B119.38 (16)
C26A—C25A—H25A120.3C24B—C25B—H25B120.3
C24A—C25A—H25A120.3C26B—C25B—H25B120.3
C25A—C26A—C27A121.0 (3)C25B—C26B—C27B120.37 (14)
C25A—C26A—H26A119.5C25B—C26B—H26B119.8
C27A—C26A—H26A119.5C27B—C26B—H26B119.8
C22A—C27A—C26A121.3 (3)C26B—C27B—C22B120.7 (2)
C22A—C27A—H27A119.3C26B—C27B—H27B119.6
C26A—C27A—H27A119.3C22B—C27B—H27B119.6
C6'A—O1'A—C2'A—C22A86.6 (2)C6'B—O1'B—C2'B—C22B85.3 (2)
C6'A—O1'A—C2'A—C5A42.9 (3)C6'B—O1'B—C2'B—C5B43.8 (3)
O7'A—C4'A—C5'A—C6'A173.7 (3)O7'B—C4'B—C5'B—C21B7.9 (4)
C5A—C4'A—C5'A—C6'A9.9 (3)C5B—C4'B—C5'B—C21B168.5 (2)
O7'A—C4'A—C5'A—C21A9.6 (4)O7'B—C4'B—C5'B—C6'B174.4 (2)
C5A—C4'A—C5'A—C21A166.7 (2)C5B—C4'B—C5'B—C6'B9.2 (3)
C2'A—O1'A—C6'A—C18A168.2 (2)C2'B—O1'B—C6'B—C18B165.2 (2)
C2'A—O1'A—C6'A—C5'A13.2 (3)C2'B—O1'B—C6'B—C5'B16.1 (3)
C21A—C5'A—C6'A—O1'A179.0 (2)C21B—C5'B—C6'B—O1'B180.0 (2)
C4'A—C5'A—C6'A—O1'A4.3 (4)C4'B—C5'B—C6'B—O1'B2.3 (4)
C21A—C5'A—C6'A—C18A2.5 (4)C21B—C5'B—C6'B—C18B1.4 (4)
C4'A—C5'A—C6'A—C18A174.2 (2)C4'B—C5'B—C6'B—C18B176.3 (2)
C5A—O1A—N2A—C3A13.4 (3)C5B—O1B—N2B—C3B13.1 (2)
O1A—N2A—C3A—C12A178.7 (2)O1B—N2B—C3B—C12B174.69 (17)
O1A—N2A—C3A—C4A2.3 (3)O1B—N2B—C3B—C4B1.1 (2)
N2A—C3A—C4A—C6A107.4 (2)N2B—C3B—C4B—C6B109.4 (2)
C12A—C3A—C4A—C6A71.5 (3)C12B—C3B—C4B—C6B63.8 (3)
N2A—C3A—C4A—C5A15.8 (3)N2B—C3B—C4B—C5B13.7 (2)
C12A—C3A—C4A—C5A165.3 (2)C12B—C3B—C4B—C5B173.02 (19)
N2A—O1A—C5A—C2'A148.3 (2)N2B—O1B—C5B—C2'B145.43 (16)
N2A—O1A—C5A—C4'A94.8 (2)N2B—O1B—C5B—C4'B97.16 (18)
N2A—O1A—C5A—C4A22.7 (2)N2B—O1B—C5B—C4B21.11 (19)
O1'A—C2'A—C5A—O1A56.2 (2)O1'B—C2'B—C5B—O1B58.1 (2)
C22A—C2'A—C5A—O1A177.86 (19)C22B—C2'B—C5B—O1B175.36 (17)
O1'A—C2'A—C5A—C4'A55.0 (2)O1'B—C2'B—C5B—C4'B53.1 (2)
C22A—C2'A—C5A—C4'A71.0 (2)C22B—C2'B—C5B—C4'B73.4 (2)
O1'A—C2'A—C5A—C4A172.36 (18)O1'B—C2'B—C5B—C4B174.35 (17)
C22A—C2'A—C5A—C4A61.7 (3)C22B—C2'B—C5B—C4B59.1 (2)
O7'A—C4'A—C5A—O1A102.7 (3)O7'B—C4'B—C5B—O1B98.7 (2)
C5'A—C4'A—C5A—O1A73.8 (2)C5'B—C4'B—C5B—O1B77.9 (2)
O7'A—C4'A—C5A—C2'A144.4 (2)O7'B—C4'B—C5B—C2'B147.2 (2)
C5'A—C4'A—C5A—C2'A39.2 (3)C5'B—C4'B—C5B—C2'B36.3 (3)
O7'A—C4'A—C5A—C4A8.8 (3)O7'B—C4'B—C5B—C4B13.0 (3)
C5'A—C4'A—C5A—C4A174.7 (2)C5'B—C4'B—C5B—C4B170.52 (18)
C3A—C4A—C5A—O1A21.9 (2)C3B—C4B—C5B—O1B19.88 (18)
C6A—C4A—C5A—O1A97.0 (2)C6B—C4B—C5B—O1B98.3 (2)
C3A—C4A—C5A—C2'A139.0 (2)C3B—C4B—C5B—C2'B137.64 (18)
C6A—C4A—C5A—C2'A20.1 (3)C6B—C4B—C5B—C2'B19.4 (3)
C3A—C4A—C5A—C4'A88.8 (2)C3B—C4B—C5B—C4'B90.7 (2)
C6A—C4A—C5A—C4'A152.31 (19)C6B—C4B—C5B—C4'B151.13 (19)
C3A—C4A—C6A—C11A133.5 (2)C3B—C4B—C6B—C11B142.3 (2)
C5A—C4A—C6A—C11A114.4 (2)C5B—C4B—C6B—C11B105.4 (2)
C3A—C4A—C6A—C7A45.4 (3)C3B—C4B—C6B—C7B37.3 (3)
C5A—C4A—C6A—C7A66.7 (3)C5B—C4B—C6B—C7B74.9 (3)
C11A—C6A—C7A—C8A1.7 (4)C11B—C6B—C7B—C8B0.7 (3)
C4A—C6A—C7A—C8A179.4 (2)C4B—C6B—C7B—C8B179.7 (2)
C6A—C7A—C8A—C9A1.7 (4)C6B—C7B—C8B—C9B0.2 (4)
C7A—C8A—C9A—C10A0.4 (4)C7B—C8B—C9B—C10B0.3 (4)
C7A—C8A—C9A—Cl1A178.4 (2)C7B—C8B—C9B—Cl2B179.15 (19)
C8A—C9A—C10A—C11A0.9 (4)C8B—C9B—C10B—C11B0.5 (4)
Cl1A—C9A—C10A—C11A179.69 (19)Cl2B—C9B—C10B—C11B178.41 (19)
C9A—C10A—C11A—C6A0.9 (4)C7B—C6B—C11B—C10B1.4 (3)
C7A—C6A—C11A—C10A0.3 (4)C4B—C6B—C11B—C10B178.9 (2)
C4A—C6A—C11A—C10A179.3 (2)C9B—C10B—C11B—C6B1.4 (4)
N2A—C3A—C12A—C13A175.0 (3)N2B—C3B—C12B—C13B150.3 (2)
C4A—C3A—C12A—C13A6.2 (4)C4B—C3B—C12B—C13B36.8 (3)
N2A—C3A—C12A—C17A2.4 (4)N2B—C3B—C12B—C17B32.1 (3)
C4A—C3A—C12A—C17A176.5 (2)C4B—C3B—C12B—C17B140.8 (2)
C17A—C12A—C13A—C14A1.6 (4)C17B—C12B—C13B—C14B1.5 (3)
C3A—C12A—C13A—C14A175.8 (2)C3B—C12B—C13B—C14B179.1 (2)
C12A—C13A—C14A—C15A0.7 (4)C12B—C13B—C14B—C15B1.1 (4)
C13A—C14A—C15A—C16A0.7 (4)C13B—C14B—C15B—C16B0.7 (4)
C13A—C14A—C15A—Cl2A178.9 (2)C13B—C14B—C15B—Cl1B179.95 (18)
C14A—C15A—C16A—C17A1.2 (4)C14B—C15B—C16B—C17B2.1 (4)
Cl2A—C15A—C16A—C17A178.4 (2)Cl1B—C15B—C16B—C17B178.7 (2)
C15A—C16A—C17A—C12A0.3 (4)C15B—C16B—C17B—C12B1.7 (4)
C13A—C12A—C17A—C16A1.1 (4)C13B—C12B—C17B—C16B0.1 (4)
C3A—C12A—C17A—C16A176.4 (2)C3B—C12B—C17B—C16B177.7 (2)
O1'A—C6'A—C18A—C19A179.9 (3)O1'B—C6'B—C18B—C19B178.8 (3)
C5'A—C6'A—C18A—C19A1.3 (4)C5'B—C6'B—C18B—C19B0.1 (4)
C6'A—C18A—C19A—C20A0.2 (5)C6'B—C18B—C19B—C20B1.4 (5)
C18A—C19A—C20A—C21A0.3 (5)C18B—C19B—C20B—C21B1.6 (5)
C19A—C20A—C21A—C5'A1.5 (5)C19B—C20B—C21B—C5'B0.3 (4)
C6'A—C5'A—C21A—C20A2.6 (4)C6'B—C5'B—C21B—C20B1.2 (4)
C4'A—C5'A—C21A—C20A174.1 (3)C4'B—C5'B—C21B—C20B176.5 (2)
O1'A—C2'A—C22A—C27A102.5 (3)O1'B—C2'B—C22B—C27B93.7 (2)
C5A—C2'A—C22A—C27A23.7 (4)C5B—C2'B—C22B—C27B33.1 (3)
O1'A—C2'A—C22A—C23A76.4 (3)O1'B—C2'B—C22B—C23B86.9 (2)
C5A—C2'A—C22A—C23A157.4 (3)C5B—C2'B—C22B—C23B146.3 (2)
C27A—C22A—C23A—C24A0.3 (5)C27B—C22B—C23B—C24B0.7 (4)
C2'A—C22A—C23A—C24A179.3 (3)C2'B—C22B—C23B—C24B178.8 (3)
C22A—C23A—C24A—C25A1.4 (7)C22B—C23B—C24B—C25B1.7 (5)
C23A—C24A—C25A—C26A1.7 (7)C23B—C24B—C25B—C26B0.9 (4)
C24A—C25A—C26A—C27A1.0 (6)C24B—C25B—C26B—C27B0.8 (2)
C23A—C22A—C27A—C26A0.5 (5)C25B—C26B—C27B—C22B1.8 (3)
C2'A—C22A—C27A—C26A178.5 (3)C23B—C22B—C27B—C26B1.0 (4)
C25A—C26A—C27A—C22A0.1 (6)C2'B—C22B—C27B—C26B179.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4A—H4A···O7A0.982.422.792 (3)102
C10A—H10A···N2B0.932.673.417 (3)138
C27A—H27A···O7A0.932.753.595 (3)151
C11A—H11A···O7Ai0.932.723.570 (3)152
C4A—H4A···O7Ai0.982.683.619 (3)161
C17A—H17A···O1Aii0.932.673.550 (3)158
C4B—H4B···O7Biii0.982.573.531 (3)167
Symmetry codes: (i) x, y+2, z; (ii) x1, y+2, z; (iii) x+1, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC29H19Cl2NO3
Mr500.35
Crystal system, space groupTriclinic, 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)
V3)2379.5 (8)
Z4
Radiation typeCu Kα
µ (mm1)2.72
Crystal size (mm)0.3 × 0.25 × 0.10
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.638, 0.762
No. of measured, independent and
observed [I > 2σ(I)] reflections
9478, 9032, 6262
Rint0.047
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.139, 1.02
No. of reflections9032
No. of parameters629
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.36

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), SDP (Frenz, 1978), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997), PARST97 (Nardelli, 1995) and PLATON (Spek, 1998).

Selected geometric parameters (Å, º) top
Cl1A—C9A1.735 (2)Cl1B—C15B1.730 (3)
Cl2A—C15A1.735 (3)Cl2B—C9B1.741 (2)
O1'A—C6'A1.354 (3)O1'B—C6'B1.359 (2)
O1'A—C2'A1.456 (3)O1'B—C2'B1.448 (3)
C2'A—C5A1.509 (3)C2'B—C22B1.506 (3)
C4'A—O7'A1.218 (3)C2'B—C5B1.524 (3)
C4'A—C5A1.531 (3)C4'B—O7'B1.214 (2)
C5'A—C6'A1.394 (3)C4'B—C5B1.533 (3)
O1A—N2A1.412 (3)C5'B—C6'B1.397 (3)
O1A—C5A1.463 (3)O1B—C5B1.465 (3)
N2A—C3A1.275 (3)N2B—C3B1.278 (3)
C3A—C4A1.508 (3)C3B—C4B1.505 (3)
C4A—C5A1.536 (3)C4B—C5B1.535 (3)
C5A—O1A—N2A—C3A13.4 (3)C5B—O1B—N2B—C3B13.1 (2)
O1A—N2A—C3A—C4A2.3 (3)O1B—N2B—C3B—C4B1.1 (2)
N2A—C3A—C4A—C5A15.8 (3)N2B—C3B—C4B—C5B13.7 (2)
N2A—O1A—C5A—C4A22.7 (2)N2B—O1B—C5B—C4B21.11 (19)
C3A—C4A—C5A—O1A21.9 (2)C3B—C4B—C5B—O1B19.88 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4A—H4A···O7'A0.982.422.792 (3)102
C10A—H10A···N2B0.932.673.417 (3)138
C27A—H27A···O7'A0.932.753.595 (3)151
C11A—H11A···O7'Ai0.932.723.570 (3)152
C4A—H4A···O7'Ai0.982.683.619 (3)161
C17A—H17A···O1Aii0.932.673.550 (3)158
C4B—H4B···O7'Biii0.982.573.531 (3)167
Symmetry codes: (i) x, y+2, z; (ii) x1, y+2, z; (iii) x+1, y+2, z+1.
 

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