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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2474.
Published online 2009 September 16. doi:  10.1107/S1600536809035296
PMCID: PMC2970366

(1R,3S)-Methyl 3-[(S)-2-(hydroxy­diphenyl­meth­yl)pyrrolidin-1-ylmeth­yl]-2,2-dimethyl­cyclo­propane­carboxyl­ate

Abstract

The asymmetric unit of the title compound, C25H31NO3, prepared from (−)-1R-cis-caronaldehyde, contains three independent mol­ecules with similar conformations. The hydr­oxy groups are involved in intra­molecular O—H(...)N hydrogen bonds. The crystal packing exhibits weak inter­molecular O—H(...)O and C—H(...)O hydrogen bonds.

Related literature

For details of the preparation of an analogous compound, see: Bakshi et al. (1989 [triangle]); Mattson et al. (1990 [triangle]). For a related structure, see: Na & Wang (2009 [triangle]).

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Object name is e-65-o2474-scheme1.jpg

Experimental

Crystal data

  • C25H31NO3
  • M r = 393.51
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2474-efi1.jpg
  • a = 34.736 (7) Å
  • b = 17.729 (4) Å
  • c = 11.013 (2) Å
  • β = 97.62 (3)°
  • V = 6722 (2) Å3
  • Z = 12
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 173 K
  • 0.50 × 0.33 × 0.29 mm

Data collection

  • Rigaku Saturn724+ CCD diffractometer
  • Absorption correction: numerical ABSCOR (Higashi, 1995 [triangle]) T min = 0.963, T max = 0.978
  • 41275 measured reflections
  • 7960 independent reflections
  • 7677 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.145
  • S = 1.17
  • 7960 reflections
  • 784 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP in SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035296/cv2590sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035296/cv2590Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

Financial support from the National Natural Science Foundation of China (grant Nos. 20472111 and 20742004) is gratefully acknowledged.

supplementary crystallographic information

Comment

In continuation of our study of new (-)-1R-cis-caronaldehyde derivatives (Na &Wang, 2009), herewith we present the crystal structure of the title compound, (I).

The asymmetric unit of (I) contains three independent molecules (Fig. 1). The hydroxy groups are involved in intramolecular O—H···N hydrogen bonds (Table 1). The crystal packing exhibits weak intermolecular O—H···O and C—H···O hydrogen bonds (Table 1).

Experimental

(1R,5S)-4-Hydroxy-6,6-dimethyl-3-oxa-bicyclo[3.1.0]-hexan-2-one1 (42.6 g, 300 mmol) was dissolved in a mixture of 250 mL of MeOH containing p-toluene sulfonic acid (10 g, 58 mmol) and refluxed for 5 hr. When reaction mixture cooled, sodium acetate (10 g) was added to mixture and MeOH was removed underreduced pressure. The residue was dissolved in N-hexane (250 mL), washed with water (3×100 mL) and freed of solvent. The residuewas taken up in 0.5% aq oxalic acid (200 mL) and stirred at room temperature for 10 h and extracted with Et2O (3×100 mL). The combined organic layer was dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure, yield 35 g coloress oily. The crude product was not purified for next step (Bakshi et al., 1989). A mixture of the previous product (20 mmol), diphenyl-pyrrolidinemethanol (20 mmol), and titanium (IV) is opropoxide (7.5 mL,12.5 mmol) was stirred at room temperature in a 100 mL flask under a drying tube. After 1 h, the viscous solution was diluted with absolute methanol (20 mL). The solution became bright yellow. Sodium cyanoborohydride (0.84 g, 13.4 mmol) was added, and the solution was stirred for 20 h. Water (4 mL) was added with stirring,and the resulting inorganic precipitate was filtered and washed with methanol.The filtrate was then concentrated in vacuo. The crude product was dissolved in ether, filtered to remove the remaining inorganic solids, and concentrated in vacuo. The product was then purified by flash chromatography. Colourless solid, m.p. 393 K; [α]20D =-5.74 (c 0.01, CHCl3) (Mattson et al., 1990).

Refinement

All H atoms were positioned geometrically [C—H 0.95-1.00 Å; O—H 0.84-0.86 Å], and refined as riding, with Uiso (H) = 1.2-1.5 Ueq of the parent atom. In the absence of anomolous scatterers, 7396 Friedel pairs were merged before the final refinement.

Figures

Fig. 1.
Three independent molecules of (I), with atomic labels and 30% probability displacement ellipsoids. H atoms omitted for clarity.

Crystal data

C25H31NO3F(000) = 2544
Mr = 393.51Dx = 1.166 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
a = 34.736 (7) ÅCell parameters from 768 reflections
b = 17.729 (4) Åθ = 2.2–27.5°
c = 11.013 (2) ŵ = 0.08 mm1
β = 97.62 (3)°T = 173 K
V = 6722 (2) Å3Strip, colourless
Z = 120.50 × 0.33 × 0.29 mm

Data collection

Rigaku Saturn724+ CCD diffractometer7960 independent reflections
Radiation source: sealed tube7677 reflections with I > 2σ(I)
graphiteRint = 0.050
ω scans at fixed χ = 45°θmax = 27.5°, θmin = 2.3°
Absorption correction: numerical ABSCOR (Higashi, 1995)h = −45→45
Tmin = 0.963, Tmax = 0.978k = −23→23
41275 measured reflectionsl = −14→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.17w = 1/[σ2(Fo2) + (0.0632P)2 + 2.6224P] where P = (Fo2 + 2Fc2)/3
7960 reflections(Δ/σ)max = 0.001
784 parametersΔρmax = 0.41 e Å3
1 restraintΔρmin = −0.24 e Å3

Special details

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)

xyzUiso*/Ueq
O1A0.61741 (6)0.71980 (12)0.0217 (2)0.0404 (5)
H1A0.60680.7249−0.05100.061*
O1C0.87641 (7)0.55390 (12)−0.0018 (2)0.0445 (5)
H1C0.88750.56140.06970.067*
O1B0.87006 (7)0.87326 (12)0.9332 (2)0.0475 (5)
H1BA0.88450.88780.99800.071*
O2B0.95265 (7)1.17966 (15)1.1925 (3)0.0608 (7)
O2A0.55251 (9)1.02781 (16)−0.2743 (3)0.0773 (9)
O2C0.95309 (8)0.84700 (15)0.3125 (4)0.0753 (9)
O3A0.49276 (7)0.98742 (15)−0.3403 (3)0.0585 (6)
O3C1.00025 (7)0.76433 (16)0.3560 (2)0.0559 (6)
O3B1.01025 (8)1.13285 (18)1.2684 (4)0.0783 (9)
N1C0.90248 (7)0.68825 (17)0.0848 (2)0.0400 (5)
N1A0.58899 (7)0.84984 (15)−0.0687 (2)0.0382 (5)
N1B0.90658 (7)0.99525 (15)1.0363 (2)0.0396 (6)
C1C0.85125 (8)0.61510 (16)−0.0382 (3)0.0342 (6)
C1A0.64291 (8)0.78108 (16)0.0535 (3)0.0340 (6)
C1B0.84952 (8)0.94225 (16)0.9081 (3)0.0364 (6)
C2A0.67399 (8)0.78459 (17)−0.0334 (3)0.0360 (6)
C2B0.82002 (8)0.95341 (16)0.9997 (3)0.0359 (6)
C2C0.82046 (9)0.62294 (18)0.0509 (3)0.0370 (6)
C3B0.79781 (9)1.01844 (19)0.9986 (3)0.0437 (7)
H3BA0.80061.05660.93980.052*
C3C0.81643 (10)0.56596 (19)0.1355 (3)0.0457 (7)
H3CA0.83220.52210.13680.055*
C3A0.69694 (8)0.84829 (19)−0.0430 (3)0.0429 (7)
H3AA0.69420.89070.00780.051*
C4B0.77159 (9)1.0288 (2)1.0822 (3)0.0499 (8)
H4BA0.75651.07361.07960.060*
C4A0.72399 (9)0.8506 (2)−0.1263 (3)0.0479 (8)
H4AA0.73950.8944−0.13140.057*
C4C0.78966 (12)0.5725 (2)0.2177 (3)0.0594 (10)
H4CA0.78740.53320.27490.071*
C5A0.72818 (9)0.7893 (2)−0.2012 (3)0.0514 (8)
H5AA0.74610.7913−0.25940.062*
C5B0.76748 (10)0.9744 (2)1.1686 (3)0.0509 (8)
H5BA0.74970.98151.22620.061*
C5C0.76616 (11)0.6356 (3)0.2178 (3)0.0587 (10)
H5CA0.74810.64010.27510.070*
C6C0.76942 (9)0.6920 (2)0.1327 (3)0.0510 (8)
H6CA0.75320.73520.13040.061*
C6A0.70623 (10)0.7253 (2)−0.1910 (3)0.0518 (8)
H6AA0.70940.6828−0.24130.062*
C6B0.78927 (11)0.9095 (2)1.1707 (3)0.0541 (9)
H6BA0.78650.87171.23000.065*
C7B0.81547 (9)0.89896 (18)1.0864 (3)0.0435 (7)
H7BA0.83030.85391.08870.052*
C7C0.79635 (9)0.6857 (2)0.0507 (3)0.0420 (6)
H7CA0.79840.7250−0.00680.050*
C7A0.67956 (9)0.72283 (18)−0.1076 (3)0.0406 (6)
H7AA0.66480.6782−0.10090.049*
C8B0.82818 (8)0.93710 (19)0.7772 (3)0.0410 (7)
C8A0.66136 (8)0.76902 (17)0.1854 (3)0.0379 (6)
C8C0.83178 (9)0.59895 (17)−0.1678 (3)0.0366 (6)
C9C0.80633 (10)0.6500 (2)−0.2317 (3)0.0488 (8)
H9CA0.80030.6957−0.19350.059*
C9A0.68768 (10)0.8206 (2)0.2450 (3)0.0534 (9)
H9AA0.69540.86310.20140.064*
C9B0.82172 (10)0.8679 (2)0.7206 (3)0.0523 (8)
H9BA0.83020.82300.76290.063*
C10A0.70284 (12)0.8108 (3)0.3671 (4)0.0645 (11)
H10A0.72090.84620.40610.077*
C10B0.80270 (13)0.8643 (3)0.6005 (4)0.0662 (12)
H10B0.79830.81660.56190.079*
C10C0.78971 (10)0.6349 (2)−0.3504 (3)0.0559 (9)
H10C0.77220.6703−0.39220.067*
C11C0.79803 (10)0.5699 (2)−0.4089 (3)0.0540 (9)
H11A0.78670.5604−0.49080.065*
C11A0.69168 (12)0.7497 (3)0.4321 (4)0.0622 (10)
H11B0.70160.74350.51610.075*
C11B0.79036 (12)0.9281 (3)0.5377 (4)0.0675 (12)
H11C0.77760.92490.45610.081*
C12B0.79658 (11)0.9970 (3)0.5934 (4)0.0611 (10)
H12A0.78801.04170.55040.073*
C12C0.82314 (12)0.5183 (2)−0.3466 (3)0.0551 (9)
H12B0.82900.4726−0.38520.066*
C12A0.66611 (12)0.6982 (2)0.3742 (3)0.0592 (9)
H12C0.65860.65570.41820.071*
C13C0.83986 (11)0.53344 (19)−0.2275 (3)0.0472 (7)
H13A0.85730.4978−0.18600.057*
C13A0.65107 (10)0.70757 (19)0.2516 (3)0.0479 (7)
H13B0.63350.67120.21270.057*
C13B0.81537 (10)1.0015 (2)0.7127 (3)0.0496 (8)
H13C0.81951.04950.75070.060*
C14A0.61745 (8)0.85411 (17)0.0434 (3)0.0353 (6)
H14A0.63430.89960.04020.042*
C14C0.87728 (8)0.68750 (18)−0.0340 (2)0.0346 (6)
H14B0.86070.7338−0.04310.042*
C14B0.88061 (8)1.00581 (17)0.9191 (3)0.0362 (6)
H14C0.86781.05630.91760.043*
C15C0.90579 (9)0.6871 (2)−0.1302 (3)0.0464 (7)
H15A0.89870.6473−0.19220.056*
H15B0.90570.7365−0.17220.056*
C15B0.90755 (9)1.0015 (2)0.8189 (3)0.0495 (8)
H15C0.89710.96590.75350.059*
H15D0.91041.05180.78190.059*
C15A0.59243 (9)0.86225 (18)0.1472 (3)0.0411 (7)
H15E0.58430.81230.17510.049*
H15F0.60670.88950.21790.049*
C16C0.94574 (10)0.6712 (3)−0.0572 (3)0.0643 (11)
H16A0.95070.6163−0.04870.077*
H16B0.96680.6950−0.09600.077*
C16A0.55793 (11)0.9070 (3)0.0899 (4)0.0615 (10)
H16C0.56390.96170.08990.074*
H16D0.53510.89860.13330.074*
C16B0.94672 (10)0.9736 (3)0.8845 (4)0.0686 (12)
H16E0.94780.91780.88820.082*
H16F0.96870.99270.84460.082*
C17A0.55103 (9)0.8763 (3)−0.0387 (3)0.0564 (9)
H17A0.53220.8341−0.04370.068*
H17B0.54050.9162−0.09670.068*
C17C0.94190 (9)0.7067 (3)0.0640 (3)0.0570 (10)
H17C0.96110.68540.12950.068*
H17D0.94560.76200.06080.068*
C17B0.94646 (9)1.0081 (3)1.0113 (4)0.0625 (11)
H17E0.96540.98261.07290.075*
H17F0.95251.06271.01080.075*
C18B0.89627 (9)1.04214 (17)1.1372 (3)0.0384 (6)
H18A0.86851.03501.14520.046*
H18B0.90041.09601.11870.046*
C18C0.88879 (9)0.73210 (18)0.1836 (3)0.0394 (6)
H18C0.86000.73330.17180.047*
H18D0.89830.78460.18090.047*
C18A0.60099 (9)0.88466 (19)−0.1784 (3)0.0429 (7)
H18E0.62840.8716−0.18390.051*
H18F0.59910.9402−0.17220.051*
C19B0.92066 (10)1.02140 (18)1.2559 (3)0.0430 (7)
H19A0.92290.96581.27010.052*
C19C0.90315 (9)0.69780 (19)0.3067 (3)0.0414 (7)
H19B0.89920.64200.30970.050*
C19A0.57583 (10)0.85798 (19)−0.2918 (3)0.0450 (7)
H19C0.57070.8025−0.29130.054*
C20A0.54190 (10)0.9032 (2)−0.3598 (3)0.0479 (8)
H20A0.51920.8715−0.39440.057*
C20B0.95673 (10)1.0655 (2)1.3112 (3)0.0492 (8)
H20B0.97781.03301.35470.059*
C20C0.93935 (9)0.72480 (19)0.3894 (3)0.0432 (7)
H20C0.95450.68380.43620.052*
C21C0.89832 (10)0.7365 (2)0.4234 (3)0.0530 (9)
C21A0.57894 (12)0.8878 (3)−0.4164 (3)0.0597 (10)
C21B0.91957 (12)1.0658 (2)1.3705 (3)0.0541 (9)
C22B0.89454 (13)1.1358 (3)1.3665 (4)0.0672 (11)
H22A0.87201.12601.40890.101*
H22B0.88571.14931.28100.101*
H22C0.90971.17751.40690.101*
C22C0.88819 (16)0.6850 (4)0.5251 (4)0.0888 (17)
H22D0.86170.69580.54160.133*
H22E0.90650.69380.59950.133*
H22F0.88990.63230.49960.133*
C22A0.60725 (14)0.9508 (3)−0.4305 (5)0.0899 (18)
H22G0.62910.9312−0.46880.135*
H22H0.61690.9716−0.34960.135*
H22I0.59410.9906−0.48210.135*
C23C0.87987 (12)0.8133 (3)0.4212 (4)0.0679 (11)
H23A0.85380.80910.44570.102*
H23B0.87790.83420.33820.102*
H23C0.89580.84670.47830.102*
C23B0.92173 (17)1.0215 (3)1.4887 (4)0.0816 (14)
H23D0.89681.02481.52080.122*
H23E0.94231.04241.54890.122*
H23F0.92750.96851.47300.122*
C23A0.57365 (16)0.8325 (3)−0.5219 (4)0.0868 (17)
H23G0.59840.8256−0.55390.130*
H23H0.55420.8521−0.58700.130*
H23I0.56480.7839−0.49320.130*
C24C0.96302 (9)0.78642 (19)0.3501 (3)0.0430 (7)
C24A0.53123 (11)0.9789 (2)−0.3215 (3)0.0505 (8)
C24B0.97119 (10)1.1316 (2)1.2508 (3)0.0510 (8)
C25C1.02614 (12)0.8199 (3)0.3171 (5)0.0731 (12)
H25A1.05250.79930.32460.110*
H25B1.02600.86500.36860.110*
H25C1.01760.83340.23140.110*
C25B1.02795 (15)1.1948 (3)1.2119 (7)0.107 (2)
H25D1.05631.19121.23050.161*
H25E1.01921.24261.24370.161*
H25F1.02051.19291.12300.161*
C25A0.47831 (16)1.0591 (3)−0.3037 (6)0.0923 (17)
H25G0.44991.0596−0.32080.139*
H25H0.48901.0997−0.34970.139*
H25I0.48631.0666−0.21580.139*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0363 (11)0.0367 (11)0.0476 (12)−0.0111 (8)0.0026 (9)−0.0030 (9)
O1C0.0513 (13)0.0406 (11)0.0414 (11)0.0158 (10)0.0051 (9)0.0032 (9)
O1B0.0438 (12)0.0351 (11)0.0637 (15)0.0087 (9)0.0080 (10)−0.0022 (10)
O2B0.0548 (14)0.0447 (13)0.0797 (19)−0.0020 (12)−0.0036 (13)0.0076 (13)
O2A0.0625 (18)0.0436 (15)0.122 (3)−0.0002 (13)−0.0030 (17)−0.0005 (16)
O2C0.0548 (16)0.0404 (14)0.132 (3)0.0018 (12)0.0165 (16)0.0139 (16)
O3A0.0514 (14)0.0556 (15)0.0687 (17)0.0116 (11)0.0085 (12)−0.0045 (13)
O3C0.0402 (12)0.0709 (17)0.0567 (15)0.0051 (11)0.0075 (10)0.0093 (13)
O3B0.0432 (15)0.0626 (17)0.125 (3)−0.0071 (13)−0.0049 (16)0.0134 (18)
N1C0.0316 (11)0.0566 (15)0.0309 (12)0.0061 (11)0.0006 (9)−0.0027 (11)
N1A0.0275 (11)0.0484 (14)0.0379 (13)−0.0046 (10)0.0013 (9)−0.0015 (11)
N1B0.0298 (12)0.0468 (14)0.0410 (13)0.0061 (10)−0.0005 (10)−0.0016 (11)
C1C0.0343 (14)0.0358 (14)0.0321 (14)0.0059 (11)0.0033 (11)0.0034 (11)
C1A0.0281 (13)0.0320 (13)0.0414 (15)−0.0067 (10)0.0033 (11)−0.0023 (11)
C1B0.0331 (14)0.0290 (13)0.0467 (16)0.0035 (10)0.0040 (11)−0.0024 (12)
C2A0.0292 (13)0.0383 (14)0.0395 (15)0.0002 (11)0.0006 (11)0.0005 (12)
C2B0.0297 (13)0.0352 (14)0.0417 (15)0.0000 (11)0.0004 (11)−0.0018 (12)
C2C0.0373 (15)0.0407 (15)0.0330 (14)−0.0035 (12)0.0051 (11)−0.0033 (12)
C3B0.0347 (15)0.0426 (16)0.0533 (18)0.0040 (12)0.0043 (13)0.0051 (14)
C3C0.058 (2)0.0418 (16)0.0381 (16)−0.0043 (14)0.0097 (14)0.0008 (13)
C3A0.0310 (14)0.0436 (16)0.0539 (19)−0.0046 (12)0.0047 (13)−0.0020 (14)
C4B0.0375 (16)0.057 (2)0.0553 (19)0.0105 (14)0.0051 (14)−0.0049 (16)
C4A0.0305 (15)0.0546 (19)0.059 (2)−0.0046 (13)0.0066 (13)0.0074 (16)
C4C0.075 (3)0.064 (2)0.0426 (19)−0.017 (2)0.0197 (17)−0.0008 (17)
C5A0.0364 (16)0.068 (2)0.051 (2)0.0043 (15)0.0102 (14)0.0079 (17)
C5B0.0411 (17)0.067 (2)0.0468 (19)−0.0021 (15)0.0118 (14)−0.0066 (16)
C5C0.052 (2)0.077 (3)0.050 (2)−0.0188 (19)0.0189 (16)−0.0196 (19)
C6C0.0376 (16)0.061 (2)0.055 (2)0.0003 (15)0.0091 (14)−0.0138 (17)
C6A0.0518 (19)0.055 (2)0.0499 (19)0.0058 (16)0.0118 (15)−0.0045 (16)
C6B0.060 (2)0.058 (2)0.0458 (19)−0.0088 (17)0.0110 (16)0.0048 (16)
C7B0.0455 (17)0.0380 (15)0.0462 (18)0.0003 (13)0.0034 (13)0.0025 (13)
C7C0.0395 (15)0.0445 (16)0.0419 (16)−0.0016 (13)0.0051 (12)−0.0014 (13)
C7A0.0392 (15)0.0414 (16)0.0408 (16)−0.0007 (12)0.0039 (12)−0.0005 (13)
C8B0.0308 (14)0.0472 (16)0.0451 (17)−0.0025 (12)0.0059 (12)−0.0080 (13)
C8A0.0326 (14)0.0393 (15)0.0411 (16)0.0015 (11)0.0024 (11)−0.0001 (12)
C8C0.0362 (14)0.0388 (15)0.0351 (14)−0.0019 (11)0.0060 (11)0.0003 (11)
C9C0.0467 (18)0.054 (2)0.0430 (18)0.0083 (15)−0.0029 (14)−0.0052 (15)
C9A0.0483 (19)0.058 (2)0.049 (2)−0.0133 (16)−0.0106 (15)0.0079 (16)
C9B0.0508 (19)0.056 (2)0.053 (2)−0.0104 (15)0.0166 (15)−0.0129 (16)
C10A0.058 (2)0.073 (3)0.057 (2)−0.0085 (19)−0.0152 (18)0.0033 (19)
C10B0.066 (2)0.083 (3)0.053 (2)−0.027 (2)0.0202 (18)−0.034 (2)
C10C0.0454 (19)0.073 (2)0.0462 (19)0.0050 (17)−0.0057 (14)−0.0041 (18)
C11C0.0471 (19)0.080 (3)0.0355 (16)−0.0170 (17)0.0056 (13)−0.0085 (16)
C11A0.062 (2)0.079 (3)0.043 (2)0.015 (2)−0.0032 (16)0.0041 (18)
C11B0.054 (2)0.106 (4)0.043 (2)−0.022 (2)0.0061 (16)−0.018 (2)
C12B0.049 (2)0.084 (3)0.047 (2)−0.0039 (19)−0.0053 (16)−0.0007 (19)
C12C0.065 (2)0.056 (2)0.0466 (19)−0.0077 (17)0.0144 (16)−0.0172 (16)
C12A0.071 (2)0.056 (2)0.050 (2)0.0044 (18)0.0096 (17)0.0093 (17)
C13C0.058 (2)0.0436 (17)0.0406 (16)0.0018 (14)0.0106 (14)−0.0033 (14)
C13A0.0536 (19)0.0441 (17)0.0467 (18)−0.0027 (14)0.0092 (14)0.0028 (14)
C13B0.0459 (18)0.054 (2)0.0450 (18)0.0022 (15)−0.0065 (14)−0.0070 (15)
C14A0.0288 (13)0.0388 (15)0.0375 (15)−0.0050 (11)0.0013 (11)−0.0013 (11)
C14C0.0316 (13)0.0428 (15)0.0286 (13)0.0001 (12)0.0012 (10)−0.0004 (11)
C14B0.0311 (14)0.0414 (15)0.0349 (14)−0.0018 (11)−0.0002 (10)0.0016 (11)
C15C0.0425 (16)0.064 (2)0.0334 (15)−0.0085 (15)0.0067 (12)−0.0019 (15)
C15B0.0390 (16)0.067 (2)0.0436 (17)−0.0078 (15)0.0086 (13)−0.0021 (15)
C15A0.0387 (15)0.0450 (17)0.0405 (16)−0.0044 (12)0.0087 (12)−0.0039 (13)
C16C0.0371 (17)0.111 (4)0.046 (2)−0.0007 (19)0.0119 (14)−0.013 (2)
C16A0.047 (2)0.082 (3)0.057 (2)0.0123 (18)0.0121 (16)0.001 (2)
C16B0.0345 (17)0.107 (4)0.065 (2)−0.0014 (19)0.0121 (16)−0.020 (2)
C17A0.0293 (16)0.086 (3)0.052 (2)0.0042 (16)0.0011 (13)−0.0020 (19)
C17C0.0313 (15)0.097 (3)0.0416 (17)−0.0010 (16)0.0021 (12)−0.0098 (18)
C17B0.0284 (16)0.097 (3)0.061 (2)−0.0005 (17)−0.0006 (14)−0.012 (2)
C18B0.0392 (15)0.0353 (14)0.0389 (15)0.0026 (11)−0.0013 (12)−0.0015 (11)
C18C0.0382 (15)0.0487 (17)0.0306 (14)0.0031 (12)0.0021 (11)−0.0033 (12)
C18A0.0344 (15)0.0462 (17)0.0474 (18)0.0016 (12)0.0027 (12)0.0074 (14)
C19B0.0513 (18)0.0361 (15)0.0388 (15)−0.0029 (13)−0.0041 (13)0.0017 (12)
C19C0.0430 (16)0.0449 (17)0.0360 (15)−0.0063 (13)0.0035 (12)0.0027 (13)
C19A0.0471 (17)0.0455 (17)0.0414 (17)0.0100 (14)0.0029 (13)0.0039 (13)
C20A0.0475 (18)0.0496 (18)0.0447 (18)0.0056 (14)−0.0002 (14)0.0057 (14)
C20B0.0498 (19)0.0471 (18)0.0472 (18)−0.0001 (14)−0.0070 (14)0.0005 (14)
C20C0.0468 (17)0.0500 (18)0.0302 (14)−0.0024 (14)−0.0049 (12)0.0039 (13)
C21C0.0491 (19)0.075 (2)0.0353 (17)−0.0121 (17)0.0066 (13)−0.0034 (16)
C21A0.065 (2)0.071 (2)0.0453 (19)0.024 (2)0.0139 (16)0.0149 (18)
C21B0.070 (2)0.051 (2)0.0382 (17)−0.0082 (17)−0.0016 (15)−0.0033 (15)
C22B0.071 (3)0.066 (3)0.066 (2)−0.002 (2)0.012 (2)−0.021 (2)
C22C0.104 (4)0.126 (4)0.039 (2)−0.045 (3)0.019 (2)−0.001 (2)
C22A0.070 (3)0.112 (4)0.092 (4)0.022 (3)0.030 (3)0.055 (3)
C23C0.052 (2)0.089 (3)0.065 (3)0.002 (2)0.0129 (18)−0.028 (2)
C23B0.115 (4)0.086 (3)0.041 (2)−0.022 (3)0.000 (2)0.000 (2)
C23A0.114 (4)0.107 (4)0.039 (2)0.054 (3)0.010 (2)0.006 (2)
C24C0.0399 (16)0.0459 (17)0.0418 (17)−0.0015 (13)0.0000 (12)−0.0039 (14)
C24A0.054 (2)0.0438 (18)0.053 (2)0.0047 (15)0.0059 (15)0.0061 (15)
C24B0.0481 (19)0.0459 (18)0.056 (2)−0.0003 (14)−0.0051 (15)−0.0046 (15)
C25C0.046 (2)0.098 (3)0.077 (3)−0.011 (2)0.0140 (19)0.010 (3)
C25B0.059 (3)0.076 (3)0.185 (7)−0.022 (3)0.015 (3)0.026 (4)
C25A0.086 (4)0.071 (3)0.127 (5)0.024 (3)0.039 (3)−0.013 (3)

Geometric parameters (Å, °)

O1A—C1A1.416 (3)C12A—H12C0.9500
O1A—H1A0.8400C13C—H13A0.9500
O1C—C1C1.417 (3)C13A—H13B0.9500
O1C—H1C0.8400C13B—H13C0.9500
O1B—C1B1.425 (3)C14A—C15A1.532 (4)
O1B—H1BA0.8552C14A—H14A1.0000
O2B—C24B1.202 (4)C14C—C15C1.543 (4)
O2A—C24A1.210 (5)C14C—H14B1.0000
O2C—C24C1.185 (4)C14B—C15B1.540 (4)
O3A—C24A1.333 (4)C14B—H14C1.0000
O3A—C25A1.443 (5)C15C—C16C1.535 (5)
O3C—C24C1.344 (4)C15C—H15A0.9900
O3C—C25C1.438 (5)C15C—H15B0.9900
O3B—C24B1.345 (4)C15B—C16B1.536 (5)
O3B—C25B1.440 (6)C15B—H15C0.9900
N1C—C17C1.455 (4)C15B—H15D0.9900
N1C—C18C1.466 (4)C15A—C16A1.505 (5)
N1C—C14C1.475 (3)C15A—H15E0.9900
N1A—C18A1.465 (4)C15A—H15F0.9900
N1A—C14A1.478 (4)C16C—C17C1.497 (5)
N1A—C17A1.478 (4)C16C—H16A0.9900
N1B—C17B1.466 (4)C16C—H16B0.9900
N1B—C18B1.469 (4)C16A—C17A1.506 (6)
N1B—C14B1.486 (4)C16A—H16C0.9900
C1C—C8C1.524 (4)C16A—H16D0.9900
C1C—C2C1.550 (4)C16B—C17B1.525 (6)
C1C—C14C1.567 (4)C16B—H16E0.9900
C1A—C8A1.522 (4)C16B—H16F0.9900
C1A—C2A1.536 (4)C17A—H17A0.9900
C1A—C14A1.564 (4)C17A—H17B0.9900
C1B—C8B1.533 (4)C17C—H17C0.9900
C1B—C2B1.543 (4)C17C—H17D0.9900
C1B—C14B1.554 (4)C17B—H17E0.9900
C2A—C3A1.395 (4)C17B—H17F0.9900
C2A—C7A1.395 (4)C18B—C19B1.507 (4)
C2B—C7B1.382 (4)C18B—H18A0.9900
C2B—C3B1.386 (4)C18B—H18B0.9900
C2C—C7C1.392 (5)C18C—C19C1.509 (4)
C2C—C3C1.394 (4)C18C—H18C0.9900
C3B—C4B1.390 (5)C18C—H18D0.9900
C3B—H3BA0.9500C18A—C19A1.503 (5)
C3C—C4C1.386 (5)C18A—H18E0.9900
C3C—H3CA0.9500C18A—H18F0.9900
C3A—C4A1.398 (5)C19B—C21B1.492 (5)
C3A—H3AA0.9500C19B—C20B1.533 (4)
C4B—C5B1.376 (5)C19B—H19A1.0000
C4B—H4BA0.9500C19C—C21C1.486 (5)
C4A—C5A1.384 (5)C19C—C20C1.528 (4)
C4A—H4AA0.9500C19C—H19B1.0000
C4C—C5C1.385 (6)C19A—C21A1.487 (5)
C4C—H4CA0.9500C19A—C20A1.536 (4)
C5A—C6A1.380 (5)C19A—H19C1.0000
C5A—H5AA0.9500C20A—C24A1.470 (5)
C5B—C6B1.375 (5)C20A—C21A1.527 (5)
C5B—H5BA0.9500C20A—H20A1.0000
C5C—C6C1.386 (6)C20B—C24B1.468 (5)
C5C—H5CA0.9500C20B—C21B1.522 (6)
C6C—C7C1.388 (4)C20B—H20B1.0000
C6C—H6CA0.9500C20C—C24C1.467 (5)
C6A—C7A1.390 (5)C20C—C21C1.535 (5)
C6A—H6AA0.9500C20C—H20C1.0000
C6B—C7B1.396 (5)C21C—C23C1.504 (6)
C6B—H6BA0.9500C21C—C22C1.522 (6)
C7B—H7BA0.9500C21A—C22A1.511 (7)
C7C—H7CA0.9500C21A—C23A1.512 (6)
C7A—H7AA0.9500C21B—C22B1.513 (6)
C8B—C9B1.381 (5)C21B—C23B1.513 (6)
C8B—C13B1.387 (5)C22B—H22A0.9800
C8A—C13A1.384 (4)C22B—H22B0.9800
C8A—C9A1.395 (4)C22B—H22C0.9800
C8C—C13C1.382 (4)C22C—H22D0.9800
C8C—C9C1.390 (4)C22C—H22E0.9800
C9C—C10C1.383 (5)C22C—H22F0.9800
C9C—H9CA0.9500C22A—H22G0.9800
C9A—C10A1.388 (5)C22A—H22H0.9800
C9A—H9AA0.9500C22A—H22I0.9800
C9B—C10B1.399 (6)C23C—H23A0.9800
C9B—H9BA0.9500C23C—H23B0.9800
C10A—C11A1.382 (6)C23C—H23C0.9800
C10A—H10A0.9500C23B—H23D0.9800
C10B—C11B1.365 (7)C23B—H23E0.9800
C10B—H10B0.9500C23B—H23F0.9800
C10C—C11C1.369 (6)C23A—H23G0.9800
C10C—H10C0.9500C23A—H23H0.9800
C11C—C12C1.382 (6)C23A—H23I0.9800
C11C—H11A0.9500C25C—H25A0.9800
C11A—C12A1.371 (6)C25C—H25B0.9800
C11A—H11B0.9500C25C—H25C0.9800
C11B—C12B1.371 (6)C25B—H25D0.9800
C11B—H11C0.9500C25B—H25E0.9800
C12B—C13B1.390 (5)C25B—H25F0.9800
C12B—H12A0.9500C25A—H25G0.9800
C12C—C13C1.388 (5)C25A—H25H0.9800
C12C—H12B0.9500C25A—H25I0.9800
C12A—C13A1.392 (5)
C1A—O1A—H1A109.5C16A—C15A—H15F111.0
C1C—O1C—H1C109.5C14A—C15A—H15F111.0
C1B—O1B—H1BA97.3H15E—C15A—H15F109.0
C24A—O3A—C25A115.7 (4)C17C—C16C—C15C102.0 (3)
C24C—O3C—C25C114.9 (3)C17C—C16C—H16A111.4
C24B—O3B—C25B115.5 (4)C15C—C16C—H16A111.4
C17C—N1C—C18C113.7 (3)C17C—C16C—H16B111.4
C17C—N1C—C14C108.8 (2)C15C—C16C—H16B111.4
C18C—N1C—C14C116.8 (2)H16A—C16C—H16B109.2
C18A—N1A—C14A115.8 (2)C15A—C16A—C17A102.9 (3)
C18A—N1A—C17A114.2 (3)C15A—C16A—H16C111.2
C14A—N1A—C17A108.3 (2)C17A—C16A—H16C111.2
C17B—N1B—C18B112.7 (3)C15A—C16A—H16D111.2
C17B—N1B—C14B107.3 (3)C17A—C16A—H16D111.2
C18B—N1B—C14B113.9 (2)H16C—C16A—H16D109.1
O1C—C1C—C8C107.5 (2)C17B—C16B—C15B100.9 (3)
O1C—C1C—C2C110.0 (2)C17B—C16B—H16E111.6
C8C—C1C—C2C110.6 (2)C15B—C16B—H16E111.6
O1C—C1C—C14C106.7 (2)C17B—C16B—H16F111.6
C8C—C1C—C14C111.3 (2)C15B—C16B—H16F111.6
C2C—C1C—C14C110.6 (2)H16E—C16B—H16F109.4
O1A—C1A—C8A107.4 (2)N1A—C17A—C16A106.8 (3)
O1A—C1A—C2A110.2 (2)N1A—C17A—H17A110.4
C8A—C1A—C2A111.0 (2)C16A—C17A—H17A110.4
O1A—C1A—C14A106.8 (2)N1A—C17A—H17B110.4
C8A—C1A—C14A110.3 (2)C16A—C17A—H17B110.4
C2A—C1A—C14A111.1 (2)H17A—C17A—H17B108.6
O1B—C1B—C8B107.4 (2)N1C—C17C—C16C104.1 (3)
O1B—C1B—C2B110.0 (2)N1C—C17C—H17C110.9
C8B—C1B—C2B110.0 (2)C16C—C17C—H17C110.9
O1B—C1B—C14B106.4 (2)N1C—C17C—H17D110.9
C8B—C1B—C14B111.2 (3)C16C—C17C—H17D110.9
C2B—C1B—C14B111.8 (2)H17C—C17C—H17D109.0
C3A—C2A—C7A117.8 (3)N1B—C17B—C16B103.3 (3)
C3A—C2A—C1A122.4 (3)N1B—C17B—H17E111.1
C7A—C2A—C1A119.8 (3)C16B—C17B—H17E111.1
C7B—C2B—C3B118.2 (3)N1B—C17B—H17F111.1
C7B—C2B—C1B120.6 (3)C16B—C17B—H17F111.1
C3B—C2B—C1B121.2 (3)H17E—C17B—H17F109.1
C7C—C2C—C3C117.8 (3)N1B—C18B—C19B110.6 (2)
C7C—C2C—C1C122.4 (3)N1B—C18B—H18A109.5
C3C—C2C—C1C119.8 (3)C19B—C18B—H18A109.5
C2B—C3B—C4B121.2 (3)N1B—C18B—H18B109.5
C2B—C3B—H3BA119.4C19B—C18B—H18B109.5
C4B—C3B—H3BA119.4H18A—C18B—H18B108.1
C4C—C3C—C2C120.8 (3)N1C—C18C—C19C110.6 (3)
C4C—C3C—H3CA119.6N1C—C18C—H18C109.5
C2C—C3C—H3CA119.6C19C—C18C—H18C109.5
C2A—C3A—C4A121.0 (3)N1C—C18C—H18D109.5
C2A—C3A—H3AA119.5C19C—C18C—H18D109.5
C4A—C3A—H3AA119.5H18C—C18C—H18D108.1
C5B—C4B—C3B120.1 (3)N1A—C18A—C19A110.8 (3)
C5B—C4B—H4BA119.9N1A—C18A—H18E109.5
C3B—C4B—H4BA119.9C19A—C18A—H18E109.5
C5A—C4A—C3A120.0 (3)N1A—C18A—H18F109.5
C5A—C4A—H4AA120.0C19A—C18A—H18F109.5
C3A—C4A—H4AA120.0H18E—C18A—H18F108.1
C5C—C4C—C3C121.0 (4)C21B—C19B—C18B122.1 (3)
C5C—C4C—H4CA119.5C21B—C19B—C20B60.4 (2)
C3C—C4C—H4CA119.5C18B—C19B—C20B123.8 (3)
C6A—C5A—C4A119.6 (3)C21B—C19B—H19A113.5
C6A—C5A—H5AA120.2C18B—C19B—H19A113.5
C4A—C5A—H5AA120.2C20B—C19B—H19A113.5
C6B—C5B—C4B119.4 (3)C21C—C19C—C18C121.9 (3)
C6B—C5B—H5BA120.3C21C—C19C—C20C61.2 (2)
C4B—C5B—H5BA120.3C18C—C19C—C20C123.8 (3)
C4C—C5C—C6C118.8 (3)C21C—C19C—H19B113.4
C4C—C5C—H5CA120.6C18C—C19C—H19B113.4
C6C—C5C—H5CA120.6C20C—C19C—H19B113.4
C5C—C6C—C7C120.3 (3)C21A—C19A—C18A123.4 (3)
C5C—C6C—H6CA119.9C21A—C19A—C20A60.6 (2)
C7C—C6C—H6CA119.9C18A—C19A—C20A124.4 (3)
C5A—C6A—C7A120.3 (3)C21A—C19A—H19C112.9
C5A—C6A—H6AA119.9C18A—C19A—H19C112.9
C7A—C6A—H6AA119.9C20A—C19A—H19C112.9
C5B—C6B—C7B120.4 (3)C24A—C20A—C21A122.6 (3)
C5B—C6B—H6BA119.8C24A—C20A—C19A122.9 (3)
C7B—C6B—H6BA119.8C21A—C20A—C19A58.1 (2)
C2B—C7B—C6B120.7 (3)C24A—C20A—H20A114.0
C2B—C7B—H7BA119.6C21A—C20A—H20A114.0
C6B—C7B—H7BA119.6C19A—C20A—H20A114.0
C6C—C7C—C2C121.4 (3)C24B—C20B—C21B123.5 (3)
C6C—C7C—H7CA119.3C24B—C20B—C19B122.5 (3)
C2C—C7C—H7CA119.3C21B—C20B—C19B58.5 (2)
C6A—C7A—C2A121.3 (3)C24B—C20B—H20B113.8
C6A—C7A—H7AA119.4C21B—C20B—H20B113.8
C2A—C7A—H7AA119.4C19B—C20B—H20B113.8
C9B—C8B—C13B118.6 (3)C24C—C20C—C19C120.5 (3)
C9B—C8B—C1B120.5 (3)C24C—C20C—C21C123.1 (3)
C13B—C8B—C1B121.0 (3)C19C—C20C—C21C58.0 (2)
C13A—C8A—C9A117.9 (3)C24C—C20C—H20C114.6
C13A—C8A—C1A120.5 (3)C19C—C20C—H20C114.6
C9A—C8A—C1A121.6 (3)C21C—C20C—H20C114.6
C13C—C8C—C9C117.5 (3)C19C—C21C—C23C120.1 (3)
C13C—C8C—C1C120.7 (3)C19C—C21C—C22C115.0 (4)
C9C—C8C—C1C121.7 (3)C23C—C21C—C22C114.6 (4)
C10C—C9C—C8C120.7 (3)C19C—C21C—C20C60.7 (2)
C10C—C9C—H9CA119.7C23C—C21C—C20C121.7 (3)
C8C—C9C—H9CA119.7C22C—C21C—C20C114.3 (4)
C10A—C9A—C8A120.9 (4)C19A—C21A—C22A119.0 (4)
C10A—C9A—H9AA119.5C19A—C21A—C23A117.5 (4)
C8A—C9A—H9AA119.5C22A—C21A—C23A114.5 (4)
C8B—C9B—C10B119.7 (4)C19A—C21A—C20A61.2 (2)
C8B—C9B—H9BA120.1C22A—C21A—C20A120.3 (4)
C10B—C9B—H9BA120.1C23A—C21A—C20A114.0 (4)
C11A—C10A—C9A120.3 (4)C19B—C21B—C22B119.1 (3)
C11A—C10A—H10A119.9C19B—C21B—C23B116.7 (3)
C9A—C10A—H10A119.9C22B—C21B—C23B114.5 (4)
C11B—C10B—C9B121.2 (4)C19B—C21B—C20B61.1 (2)
C11B—C10B—H10B119.4C22B—C21B—C20B120.5 (3)
C9B—C10B—H10B119.4C23B—C21B—C20B114.8 (4)
C11C—C10C—C9C121.3 (4)C21B—C22B—H22A109.5
C11C—C10C—H10C119.3C21B—C22B—H22B109.5
C9C—C10C—H10C119.3H22A—C22B—H22B109.5
C10C—C11C—C12C118.8 (3)C21B—C22B—H22C109.5
C10C—C11C—H11A120.6H22A—C22B—H22C109.5
C12C—C11C—H11A120.6H22B—C22B—H22C109.5
C12A—C11A—C10A119.4 (4)C21C—C22C—H22D109.5
C12A—C11A—H11B120.3C21C—C22C—H22E109.5
C10A—C11A—H11B120.3H22D—C22C—H22E109.5
C10B—C11B—C12B119.4 (4)C21C—C22C—H22F109.5
C10B—C11B—H11C120.3H22D—C22C—H22F109.5
C12B—C11B—H11C120.3H22E—C22C—H22F109.5
C11B—C12B—C13B120.1 (4)C21A—C22A—H22G109.5
C11B—C12B—H12A120.0C21A—C22A—H22H109.5
C13B—C12B—H12A120.0H22G—C22A—H22H109.5
C11C—C12C—C13C119.9 (3)C21A—C22A—H22I109.5
C11C—C12C—H12B120.0H22G—C22A—H22I109.5
C13C—C12C—H12B120.0H22H—C22A—H22I109.5
C11A—C12A—C13A120.5 (4)C21C—C23C—H23A109.5
C11A—C12A—H12C119.7C21C—C23C—H23B109.5
C13A—C12A—H12C119.7H23A—C23C—H23B109.5
C8C—C13C—C12C121.7 (3)C21C—C23C—H23C109.5
C8C—C13C—H13A119.1H23A—C23C—H23C109.5
C12C—C13C—H13A119.1H23B—C23C—H23C109.5
C8A—C13A—C12A121.0 (3)C21B—C23B—H23D109.5
C8A—C13A—H13B119.5C21B—C23B—H23E109.5
C12A—C13A—H13B119.5H23D—C23B—H23E109.5
C8B—C13B—C12B121.0 (3)C21B—C23B—H23F109.5
C8B—C13B—H13C119.5H23D—C23B—H23F109.5
C12B—C13B—H13C119.5H23E—C23B—H23F109.5
N1A—C14A—C15A104.2 (2)C21A—C23A—H23G109.5
N1A—C14A—C1A109.1 (2)C21A—C23A—H23H109.5
C15A—C14A—C1A113.3 (2)H23G—C23A—H23H109.5
N1A—C14A—H14A110.0C21A—C23A—H23I109.5
C15A—C14A—H14A110.0H23G—C23A—H23I109.5
C1A—C14A—H14A110.0H23H—C23A—H23I109.5
N1C—C14C—C15C104.5 (2)O2C—C24C—O3C121.0 (3)
N1C—C14C—C1C107.8 (2)O2C—C24C—C20C129.0 (3)
C15C—C14C—C1C113.4 (2)O3C—C24C—C20C110.0 (3)
N1C—C14C—H14B110.3O2A—C24A—O3A121.9 (3)
C15C—C14C—H14B110.3O2A—C24A—C20A127.9 (4)
C1C—C14C—H14B110.3O3A—C24A—C20A110.1 (3)
N1B—C14B—C15B105.1 (2)O2B—C24B—O3B121.6 (4)
N1B—C14B—C1B108.2 (2)O2B—C24B—C20B128.1 (3)
C15B—C14B—C1B113.0 (3)O3B—C24B—C20B110.3 (3)
N1B—C14B—H14C110.2O3C—C25C—H25A109.5
C15B—C14B—H14C110.2O3C—C25C—H25B109.5
C1B—C14B—H14C110.2H25A—C25C—H25B109.5
C16C—C15C—C14C105.0 (3)O3C—C25C—H25C109.5
C16C—C15C—H15A110.7H25A—C25C—H25C109.5
C14C—C15C—H15A110.7H25B—C25C—H25C109.5
C16C—C15C—H15B110.7O3B—C25B—H25D109.5
C14C—C15C—H15B110.7O3B—C25B—H25E109.5
H15A—C15C—H15B108.8H25D—C25B—H25E109.5
C16B—C15B—C14B105.3 (3)O3B—C25B—H25F109.5
C16B—C15B—H15C110.7H25D—C25B—H25F109.5
C14B—C15B—H15C110.7H25E—C25B—H25F109.5
C16B—C15B—H15D110.7O3A—C25A—H25G109.5
C14B—C15B—H15D110.7O3A—C25A—H25H109.5
H15C—C15B—H15D108.8H25G—C25A—H25H109.5
C16A—C15A—C14A103.6 (3)O3A—C25A—H25I109.5
C16A—C15A—H15E111.0H25G—C25A—H25I109.5
C14A—C15A—H15E111.0H25H—C25A—H25I109.5
O1A—C1A—C2A—C3A164.3 (3)O1C—C1C—C14C—C15C66.5 (3)
C8A—C1A—C2A—C3A−76.9 (3)C8C—C1C—C14C—C15C−50.6 (3)
C14A—C1A—C2A—C3A46.2 (4)C2C—C1C—C14C—C15C−174.0 (2)
O1A—C1A—C2A—C7A−14.8 (4)C17B—N1B—C14B—C15B16.6 (4)
C8A—C1A—C2A—C7A104.0 (3)C18B—N1B—C14B—C15B142.0 (3)
C14A—C1A—C2A—C7A−132.9 (3)C17B—N1B—C14B—C1B137.6 (3)
O1B—C1B—C2B—C7B−2.5 (4)C18B—N1B—C14B—C1B−97.0 (3)
C8B—C1B—C2B—C7B115.5 (3)O1B—C1B—C14B—N1B−49.2 (3)
C14B—C1B—C2B—C7B−120.5 (3)C8B—C1B—C14B—N1B−165.8 (2)
O1B—C1B—C2B—C3B176.5 (3)C2B—C1B—C14B—N1B70.9 (3)
C8B—C1B—C2B—C3B−65.4 (4)O1B—C1B—C14B—C15B66.7 (3)
C14B—C1B—C2B—C3B58.5 (4)C8B—C1B—C14B—C15B−49.9 (3)
O1C—C1C—C2C—C7C168.5 (3)C2B—C1B—C14B—C15B−173.2 (3)
C8C—C1C—C2C—C7C−72.9 (4)N1C—C14C—C15C—C16C11.4 (4)
C14C—C1C—C2C—C7C50.9 (4)C1C—C14C—C15C—C16C−105.7 (3)
O1C—C1C—C2C—C3C−11.1 (4)N1B—C14B—C15B—C16B10.5 (4)
C8C—C1C—C2C—C3C107.5 (3)C1B—C14B—C15B—C16B−107.2 (3)
C14C—C1C—C2C—C3C−128.7 (3)N1A—C14A—C15A—C16A−33.1 (3)
C7B—C2B—C3B—C4B−0.1 (5)C1A—C14A—C15A—C16A−151.6 (3)
C1B—C2B—C3B—C4B−179.2 (3)C14C—C15C—C16C—C17C−31.1 (4)
C7C—C2C—C3C—C4C−1.0 (5)C14A—C15A—C16A—C17A37.4 (4)
C1C—C2C—C3C—C4C178.6 (3)C14B—C15B—C16B—C17B−32.1 (4)
C7A—C2A—C3A—C4A1.4 (5)C18A—N1A—C17A—C16A−123.1 (3)
C1A—C2A—C3A—C4A−177.6 (3)C14A—N1A—C17A—C16A7.6 (4)
C2B—C3B—C4B—C5B0.5 (5)C15A—C16A—C17A—N1A−28.2 (4)
C2A—C3A—C4A—C5A0.3 (5)C18C—N1C—C17C—C16C−166.1 (3)
C2C—C3C—C4C—C5C0.2 (6)C14C—N1C—C17C—C16C−34.1 (4)
C3A—C4A—C5A—C6A−1.7 (5)C15C—C16C—C17C—N1C39.6 (4)
C3B—C4B—C5B—C6B−0.5 (5)C18B—N1B—C17B—C16B−163.7 (3)
C3C—C4C—C5C—C6C0.9 (6)C14B—N1B—C17B—C16B−37.5 (4)
C4C—C5C—C6C—C7C−1.2 (5)C15B—C16B—C17B—N1B42.4 (4)
C4A—C5A—C6A—C7A1.2 (5)C17B—N1B—C18B—C19B−64.5 (4)
C4B—C5B—C6B—C7B0.2 (5)C14B—N1B—C18B—C19B173.0 (3)
C3B—C2B—C7B—C6B−0.2 (5)C17C—N1C—C18C—C19C−82.3 (3)
C1B—C2B—C7B—C6B178.9 (3)C14C—N1C—C18C—C19C149.7 (3)
C5B—C6B—C7B—C2B0.1 (5)C14A—N1A—C18A—C19A163.5 (3)
C5C—C6C—C7C—C2C0.4 (5)C17A—N1A—C18A—C19A−69.6 (4)
C3C—C2C—C7C—C6C0.7 (5)N1B—C18B—C19B—C21B172.8 (3)
C1C—C2C—C7C—C6C−178.9 (3)N1B—C18B—C19B—C20B99.2 (4)
C5A—C6A—C7A—C2A0.7 (5)N1C—C18C—C19C—C21C171.3 (3)
C3A—C2A—C7A—C6A−1.9 (5)N1C—C18C—C19C—C20C96.6 (4)
C1A—C2A—C7A—C6A177.2 (3)N1A—C18A—C19A—C21A175.2 (3)
O1B—C1B—C8B—C9B18.7 (4)N1A—C18A—C19A—C20A100.3 (4)
C2B—C1B—C8B—C9B−101.0 (3)C21A—C19A—C20A—C24A−110.7 (4)
C14B—C1B—C8B—C9B134.7 (3)C18A—C19A—C20A—C24A1.6 (5)
O1B—C1B—C8B—C13B−160.5 (3)C18A—C19A—C20A—C21A112.3 (4)
C2B—C1B—C8B—C13B79.8 (4)C21B—C19B—C20B—C24B−112.1 (4)
C14B—C1B—C8B—C13B−44.5 (4)C18B—C19B—C20B—C24B−1.3 (5)
O1A—C1A—C8A—C13A−1.8 (4)C18B—C19B—C20B—C21B110.8 (4)
C2A—C1A—C8A—C13A−122.3 (3)C21C—C19C—C20C—C24C−112.3 (4)
C14A—C1A—C8A—C13A114.1 (3)C18C—C19C—C20C—C24C−1.3 (5)
O1A—C1A—C8A—C9A−179.0 (3)C18C—C19C—C20C—C21C111.0 (4)
C2A—C1A—C8A—C9A60.5 (4)C18C—C19C—C21C—C23C−2.1 (5)
C14A—C1A—C8A—C9A−63.1 (4)C20C—C19C—C21C—C23C111.9 (4)
O1C—C1C—C8C—C13C0.5 (4)C18C—C19C—C21C—C22C141.1 (4)
C2C—C1C—C8C—C13C−119.6 (3)C20C—C19C—C21C—C22C−105.0 (4)
C14C—C1C—C8C—C13C117.0 (3)C18C—C19C—C21C—C20C−113.9 (3)
O1C—C1C—C8C—C9C−177.5 (3)C24C—C20C—C21C—C19C107.8 (3)
C2C—C1C—C8C—C9C62.4 (4)C24C—C20C—C21C—C23C−1.4 (5)
C14C—C1C—C8C—C9C−61.0 (4)C19C—C20C—C21C—C23C−109.2 (4)
C13C—C8C—C9C—C10C0.4 (5)C24C—C20C—C21C—C22C−146.0 (3)
C1C—C8C—C9C—C10C178.5 (3)C19C—C20C—C21C—C22C106.2 (4)
C13A—C8A—C9A—C10A−0.4 (6)C18A—C19A—C21A—C22A−3.3 (5)
C1A—C8A—C9A—C10A176.8 (4)C20A—C19A—C21A—C22A110.7 (4)
C13B—C8B—C9B—C10B0.2 (5)C18A—C19A—C21A—C23A142.3 (4)
C1B—C8B—C9B—C10B−179.1 (3)C20A—C19A—C21A—C23A−103.7 (4)
C8A—C9A—C10A—C11A−0.7 (7)C18A—C19A—C21A—C20A−114.0 (4)
C8B—C9B—C10B—C11B0.1 (6)C24A—C20A—C21A—C19A111.2 (4)
C8C—C9C—C10C—C11C−0.7 (6)C24A—C20A—C21A—C22A2.5 (5)
C9C—C10C—C11C—C12C0.9 (6)C19A—C20A—C21A—C22A−108.7 (4)
C9A—C10A—C11A—C12A1.3 (7)C24A—C20A—C21A—C23A−139.4 (4)
C9B—C10B—C11B—C12B−0.2 (6)C19A—C20A—C21A—C23A109.5 (4)
C10B—C11B—C12B—C13B0.1 (6)C18B—C19B—C21B—C22B−2.7 (5)
C10C—C11C—C12C—C13C−0.9 (5)C20B—C19B—C21B—C22B110.8 (4)
C10A—C11A—C12A—C13A−0.8 (6)C18B—C19B—C21B—C23B141.5 (4)
C9C—C8C—C13C—C12C−0.4 (5)C20B—C19B—C21B—C23B−105.0 (4)
C1C—C8C—C13C—C12C−178.5 (3)C18B—C19B—C21B—C20B−113.5 (3)
C11C—C12C—C13C—C8C0.7 (5)C24B—C20B—C21B—C19B110.5 (4)
C9A—C8A—C13A—C12A0.9 (5)C24B—C20B—C21B—C22B1.8 (5)
C1A—C8A—C13A—C12A−176.4 (3)C19B—C20B—C21B—C22B−108.7 (4)
C11A—C12A—C13A—C8A−0.3 (6)C24B—C20B—C21B—C23B−141.4 (4)
C9B—C8B—C13B—C12B−0.3 (5)C19B—C20B—C21B—C23B108.1 (4)
C1B—C8B—C13B—C12B178.9 (3)C25C—O3C—C24C—O2C1.5 (5)
C11B—C12B—C13B—C8B0.1 (6)C25C—O3C—C24C—C20C178.8 (3)
C18A—N1A—C14A—C15A145.6 (3)C19C—C20C—C24C—O2C51.1 (6)
C17A—N1A—C14A—C15A15.8 (3)C21C—C20C—C24C—O2C−18.4 (6)
C18A—N1A—C14A—C1A−93.1 (3)C19C—C20C—C24C—O3C−125.9 (3)
C17A—N1A—C14A—C1A137.1 (3)C21C—C20C—C24C—O3C164.6 (3)
O1A—C1A—C14A—N1A−42.5 (3)C25A—O3A—C24A—O2A1.5 (6)
C8A—C1A—C14A—N1A−158.8 (2)C25A—O3A—C24A—C20A178.6 (4)
C2A—C1A—C14A—N1A77.6 (3)C21A—C20A—C24A—O2A−37.4 (6)
O1A—C1A—C14A—C15A73.1 (3)C19A—C20A—C24A—O2A33.1 (6)
C8A—C1A—C14A—C15A−43.2 (3)C21A—C20A—C24A—O3A145.6 (3)
C2A—C1A—C14A—C15A−166.7 (2)C19A—C20A—C24A—O3A−143.8 (3)
C17C—N1C—C14C—C15C13.7 (4)C25B—O3B—C24B—O2B−0.6 (7)
C18C—N1C—C14C—C15C144.0 (3)C25B—O3B—C24B—C20B179.2 (4)
C17C—N1C—C14C—C1C134.5 (3)C21B—C20B—C24B—O2B−34.9 (6)
C18C—N1C—C14C—C1C−95.1 (3)C19B—C20B—C24B—O2B36.3 (6)
O1C—C1C—C14C—N1C−48.6 (3)C21B—C20B—C24B—O3B145.3 (3)
C8C—C1C—C14C—N1C−165.7 (2)C19B—C20B—C24B—O3B−143.4 (4)
C2C—C1C—C14C—N1C70.9 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1B—H1BA···N1B0.862.082.682 (4)127
O1A—H1A···N1A0.842.302.650 (4)105
O1C—H1C···N1C0.842.312.679 (4)107
C14C—H14B···O1Bi1.002.513.319 (4)138
C19B—H19A···O2Cii1.002.373.321 (4)158
O1A—H1A···O2Biii0.842.553.236 (4)140

Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1; (iii) −x+3/2, y−1/2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2590).

References

  • Bakshi, D., Mahindroo, V. K., Soman, R. & Dev, S. (1989). Tetrahedron, 45, 767–74.
  • Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
  • Mattson, R. J., Pham, K. M., Leuck, D. J. & Cowen, K. A. (1990). J Org Chem 55, 2552–2554.
  • Na, R. & Wang, M. (2009). Acta Cryst. E65, o1230. [PMC free article] [PubMed]
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst A64, 112–122. [PubMed]

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