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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1092.
Published online 2010 April 17. doi:  10.1107/S1600536810013425
PMCID: PMC2979290

(3S,4R)-3-Ethyl-4-hydr­oxy-3-(3-methoxy­phen­yl)-1-methyl­azepanium (2R,3R)-2,3-bis­(benzo­yloxy)-3-carboxy­propionate

Abstract

The crystal structure of the title compound, C16H26NO2 +·C18H13O8 , is stabilized by an extensive network of classical N—H(...)O and O—H(...)O hydrogen bonding. The crystal structure also shows an ammonium-driven diastereo­isomerism.

Related literature

For the synthesis of the racemic compound, see: Hao et al. (2005 [triangle]). For conformational studies of seven-membered rings, see: Eliel et al. (1994 [triangle]); Entrena et al. (2005 [triangle]). For a related structure, see: Wang et al. (2008 [triangle]).

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Object name is e-66-o1092-scheme1.jpg

Experimental

Crystal data

  • C16H26NO2 +·C18H13O8
  • M r = 621.66
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1092-efi1.jpg
  • a = 7.772 (3) Å
  • b = 14.603 (6) Å
  • c = 15.060 (6) Å
  • α = 75.313 (6)°
  • β = 82.182 (6)°
  • γ = 88.367 (6)°
  • V = 1638.0 (11) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 295 K
  • 0.25 × 0.15 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.977, T max = 0.991
  • 8191 measured reflections
  • 5753 independent reflections
  • 2826 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.110
  • S = 0.80
  • 5753 reflections
  • 795 parameters
  • 16 restraints
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810013425/rk2195sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013425/rk2195Isup2.hkl

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

Acknowledgments

This work was funded in part by the National Natural Science Foundation of China (grant No. 30472088).

supplementary crystallographic information

Comment

The overall shape of the title compound can be described as two domains (Fig. 1), viz, a multi-substituted azepane and a L-dibenzoyltartrate anion. The absolute configuration of azepane ring atoms were established as C3(S) and C4(R), according to the reference molecule L-dibenzoyltartaric acid. Molecules are linked by classical N—H···O and O—H···O hydrogen bonds involving all potential donors (Table 1). The 3-methoxyphenyl substituent at C3 is cis-configuration to the OH group at C4, resulting in an extended conformation of the cation.

Surprisingly, the solid-state structure of the molecule reveals an ammonium-driven diastereoisomerism. The protonated N1 bears S, while the corresponding N2 bears R. In addition, the conformations of the two azepane rings are also different, but both of them could be identified as twist-chair forms, which are believed the most preferred conformations in seven-membered rings (Eliel et al., 1994; Entrena et al., 2005). It's worth noting that such phenomenon was not oberserved in its diastereomers, like D-tartrate salt of the (3S,4S)-isomer (Wang et al., 2008). The unique result here could be attributed to the flexibility of the azepane, which can present different conformations in similar energy.

Experimental

The title compound was prepared by standard procedures upon optical resolution of racemate. The synthesis of the racemic compound was described by Hao et al., (2005). The title compound' configuration is determined, via the known absolute configuration of the anions (2R, 3R), which is a common acid to resolve racemic amines.

Refinement

The H atoms were positioned geometrically and refined as riding (C—H = 0.93–0.97Å, N—H = 0.89Å, O—H = 0.82Å), with Uiso(H) = 1.2Ueq(C) and the three H atoms of the methyl refined as riding (C—H = 0.98Å), with Uiso(H) = 1.5Ueq(C).

Pure diffraction experiment (ratio observed/unique reflections 49%) we explain by weak diffraction of the crystal.

The 1170 Friedel pairs were merged.

Figures

Fig. 1.
The molecular structure of the title compound with the atom numbering scheme. Displasement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.

Crystal data

C16H26NO2+·C18H13O8Z = 2
Mr = 621.66F(000) = 660
Triclinic, P1Dx = 1.260 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.772 (3) ÅCell parameters from 802 reflections
b = 14.603 (6) Åθ = 2.8–19.5°
c = 15.060 (6) ŵ = 0.09 mm1
α = 75.313 (6)°T = 295 K
β = 82.182 (6)°Parallelepiped, colourless
γ = 88.367 (6)°0.25 × 0.15 × 0.10 mm
V = 1638.0 (11) Å3

Data collection

Bruker SMART APEX CCD area-detector diffractometer5753 independent reflections
Radiation source: fine-focus sealed tube2826 reflections with I > 2σ(I)
graphiteRint = 0.034
[var phi] and ω scansθmax = 25.2°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.977, Tmax = 0.991k = −16→17
8191 measured reflectionsl = −18→17

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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 0.80w = 1/[σ2(Fo2) + (0.0505P)2] where P = (Fo2 + 2Fc2)/3
5753 reflections(Δ/σ)max < 0.001
795 parametersΔρmax = 0.19 e Å3
16 restraintsΔρmin = −0.19 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
N10.1267 (6)0.8021 (3)0.0702 (3)0.0527 (12)
H10.16450.76170.11840.063*
O10.0083 (7)1.1593 (4)0.3418 (4)0.1107 (19)
O20.2316 (5)1.0406 (3)0.0160 (3)0.0681 (12)
H2X0.28821.0897−0.00420.102*
C1−0.0586 (9)1.1148 (5)0.2846 (5)0.0655 (18)
C20.0504 (8)1.0513 (4)0.2549 (4)0.0613 (17)
H20.15771.04000.27620.074*
C30.0037 (7)1.0018 (4)0.1921 (4)0.0479 (14)
C4−0.1594 (9)1.0219 (4)0.1656 (4)0.0673 (18)
H4−0.19610.99260.12330.081*
C5−0.2679 (9)1.0837 (5)0.1996 (6)0.087 (2)
H5−0.37871.09250.18220.104*
C6−0.2200 (9)1.1326 (5)0.2579 (5)0.074 (2)
H6−0.29381.17620.27880.089*
C7−0.0919 (13)1.2314 (6)0.3748 (7)0.141 (4)
H7A−0.09791.28640.32440.212*
H7B−0.03751.24790.42220.212*
H7C−0.20711.20790.39980.212*
C80.1294 (7)0.9302 (4)0.1599 (4)0.0436 (13)
C90.2899 (7)0.9882 (4)0.0996 (4)0.0505 (15)
H90.32171.03390.13240.061*
C100.4512 (7)0.9319 (4)0.0800 (4)0.0586 (16)
H10A0.53600.97630.03960.070*
H10B0.49750.90870.13820.070*
C110.4455 (8)0.8496 (5)0.0383 (5)0.077 (2)
H11A0.46330.79250.08560.092*
H11B0.54320.8556−0.01030.092*
C120.2830 (8)0.8353 (5)−0.0022 (4)0.0695 (19)
H12A0.30690.7891−0.03850.083*
H12B0.25470.8945−0.04380.083*
C130.0350 (7)0.8796 (4)0.1046 (4)0.0497 (15)
H13A−0.07190.85350.14270.060*
H13B0.00260.92660.05150.060*
C140.1910 (7)0.8608 (4)0.2444 (4)0.0526 (15)
H14A0.27290.81750.22240.063*
H14B0.25330.89660.27630.063*
C150.0492 (8)0.8022 (4)0.3150 (4)0.0696 (19)
H15A−0.03620.84380.33540.104*
H15B0.10020.76530.36710.104*
H15C−0.00510.76080.28650.104*
C160.0031 (8)0.7502 (4)0.0333 (4)0.0673 (18)
H16A−0.09410.72850.08000.101*
H16B0.06050.69690.01630.101*
H16C−0.03690.7916−0.02010.101*
N20.3412 (8)0.3378 (4)0.0241 (4)0.099 (2)
H2A0.33980.38450.05250.119*
O30.3518 (6)0.8128 (3)−0.2301 (3)0.0853 (14)
O40.1594 (5)0.5076 (3)0.0450 (3)0.0671 (12)
H4X0.08560.53620.07160.101*
C210.4215 (9)0.7309 (5)−0.1845 (4)0.0609 (17)
C220.3197 (8)0.6523 (4)−0.1683 (4)0.0557 (16)
H220.21240.6581−0.18990.067*
C230.3720 (7)0.5635 (4)−0.1202 (4)0.0527 (16)
C240.5353 (8)0.5589 (5)−0.0888 (5)0.084 (2)
H240.57760.5010−0.05790.101*
C250.6320 (11)0.6402 (7)−0.1041 (7)0.106 (3)
H250.73650.6368−0.07980.127*
C260.5800 (10)0.7256 (6)−0.1535 (6)0.084 (2)
H260.65030.7790−0.16590.101*
C270.4469 (11)0.9008 (5)−0.2537 (5)0.104 (3)
H27A0.47470.9145−0.19830.157*
H27B0.37710.9508−0.28500.157*
H27C0.55210.8957−0.29360.157*
C280.2545 (7)0.4771 (4)−0.1023 (4)0.0492 (15)
C290.0952 (8)0.4885 (5)−0.0333 (4)0.0651 (18)
H290.02840.5432−0.06240.078*
C30−0.0287 (8)0.3998 (6)0.0010 (5)0.087 (2)
H30A−0.14440.42080.01970.104*
H30B−0.03500.3719−0.05040.104*
C310.0271 (11)0.3245 (5)0.0811 (5)0.095 (3)
H31A0.02700.35330.13240.114*
H31B−0.06290.27610.09960.114*
C320.1907 (11)0.2767 (5)0.0714 (5)0.083 (2)
H32A0.17850.22950.03750.100*
H32B0.21570.24350.13270.100*
C330.3472 (8)0.3816 (6)−0.0691 (5)0.086 (2)
H33A0.30120.3369−0.09780.103*
H33B0.46880.3911−0.09440.103*
C340.1910 (8)0.4722 (4)−0.1929 (4)0.0628 (18)
H34A0.11130.4191−0.17940.075*
H34B0.12550.5292−0.21460.075*
C350.3281 (9)0.4621 (5)−0.2713 (4)0.088 (2)
H35A0.42060.5066−0.27780.133*
H35B0.27750.4745−0.32780.133*
H35C0.37330.3990−0.25790.133*
C360.5075 (11)0.2821 (6)0.0447 (5)0.122 (3)
H36A0.52250.23480.01030.183*
H36B0.49870.25210.10980.183*
H36C0.60540.32450.02710.183*
O50.9452 (8)−0.0629 (3)0.8618 (3)0.0992 (17)
O60.9088 (5)0.0795 (3)0.7676 (2)0.0524 (10)
O71.2214 (5)0.1267 (3)0.7907 (3)0.0716 (12)
H7X1.30740.11890.81770.107*
O81.1174 (5)0.2261 (3)0.8756 (3)0.0726 (13)
O90.5471 (6)0.1132 (4)0.9168 (4)0.117 (2)
O100.5145 (5)0.1943 (3)0.7770 (3)0.0781 (14)
O110.8346 (4)0.2695 (3)0.7461 (2)0.0498 (10)
O120.7405 (5)0.3877 (3)0.8101 (3)0.0749 (13)
C411.0994 (8)0.1653 (5)0.8366 (4)0.0555 (16)
C420.9188 (7)0.1249 (4)0.8400 (4)0.0490 (15)
H420.89020.07830.89950.059*
C430.7844 (6)0.2025 (4)0.8329 (4)0.0456 (14)
H430.79140.23380.88270.055*
C440.5973 (7)0.1672 (5)0.8413 (5)0.0556 (16)
C450.9283 (8)−0.0146 (5)0.7871 (5)0.0623 (17)
C460.9312 (6)−0.0507 (4)0.7052 (3)0.0660 (18)
C470.8973 (7)0.0068 (3)0.6206 (4)0.103 (3)
H470.87630.07100.61450.124*
C480.8949 (9)−0.0316 (5)0.5452 (3)0.153 (5)
H480.87230.00690.48870.184*
C490.9264 (9)−0.1275 (5)0.5544 (4)0.139 (4)
H490.9248−0.15320.50400.167*
C500.9603 (7)−0.1850 (4)0.6389 (5)0.130 (4)
H500.9813−0.24920.64510.156*
C510.9627 (6)−0.1466 (4)0.7143 (4)0.095 (3)
H510.9853−0.18510.77090.114*
C520.8058 (8)0.3597 (5)0.7438 (4)0.0556 (16)
C530.8647 (8)0.4249 (5)0.6522 (4)0.0573 (16)
C540.9568 (11)0.3910 (5)0.5829 (5)0.093 (3)
H540.98100.32670.59280.112*
C551.0134 (16)0.4525 (7)0.4984 (6)0.144 (4)
H551.07830.42990.45190.173*
C560.9737 (16)0.5470 (8)0.4832 (6)0.132 (4)
H561.01010.58800.42580.158*
C570.8808 (14)0.5815 (6)0.5517 (7)0.118 (3)
H570.85370.64550.54130.142*
C580.8279 (10)0.5192 (5)0.6369 (5)0.088 (2)
H580.76650.54200.68420.106*
O130.4031 (7)0.3360 (3)0.2308 (3)0.0842 (14)
O140.4754 (4)0.4456 (3)0.3002 (2)0.0474 (9)
O150.1637 (5)0.5055 (3)0.2669 (3)0.0712 (13)
H150.06800.53030.26350.085*
O160.2626 (5)0.6433 (3)0.1736 (3)0.0685 (12)
O170.8683 (5)0.5661 (3)0.2735 (3)0.0748 (13)
O180.8313 (5)0.5233 (3)0.1457 (3)0.0767 (13)
O190.5475 (4)0.6277 (3)0.2977 (2)0.0465 (9)
O200.6701 (5)0.7679 (3)0.2244 (3)0.0632 (11)
C610.2803 (8)0.5636 (5)0.2179 (4)0.0500 (15)
C620.4637 (6)0.5201 (4)0.2181 (3)0.0412 (13)
H620.49280.49510.16340.049*
C630.5935 (7)0.5941 (4)0.2166 (3)0.0436 (14)
H630.58500.64680.16220.052*
C640.7800 (7)0.5580 (4)0.2117 (4)0.0521 (15)
C650.4332 (7)0.3582 (5)0.2999 (4)0.0540 (16)
C660.4315 (8)0.2927 (4)0.3917 (4)0.0566 (16)
C670.3754 (10)0.2014 (5)0.4064 (5)0.086 (2)
H670.34090.18180.35730.103*
C680.3682 (14)0.1371 (6)0.4925 (7)0.125 (4)
H680.33030.07520.50130.150*
C690.4179 (16)0.1670 (7)0.5627 (7)0.137 (4)
H690.40520.12650.62180.165*
C700.4871 (14)0.2563 (7)0.5494 (5)0.125 (3)
H700.53200.27290.59740.150*
C710.4891 (10)0.3209 (5)0.4643 (5)0.082 (2)
H710.52850.38250.45570.099*
C720.5936 (7)0.7161 (5)0.2930 (4)0.0481 (15)
C730.5347 (6)0.7444 (3)0.3800 (3)0.0556 (16)
C740.5617 (6)0.8376 (3)0.3815 (3)0.079 (2)
H740.61910.87970.32960.095*
C750.5027 (7)0.8680 (3)0.4605 (4)0.117 (3)
H750.52070.93040.46150.141*
C760.4168 (8)0.8052 (5)0.5381 (3)0.131 (4)
H760.37730.82550.59100.157*
C770.3898 (7)0.7119 (5)0.5366 (3)0.124 (3)
H770.33230.66980.58850.148*
C780.4488 (7)0.6815 (3)0.4576 (4)0.089 (2)
H780.43080.61910.45660.106*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.058 (3)0.048 (3)0.051 (3)0.003 (3)−0.007 (3)−0.011 (2)
O10.103 (4)0.123 (5)0.139 (5)0.022 (3)−0.019 (4)−0.094 (4)
O20.056 (3)0.053 (3)0.077 (3)−0.007 (2)−0.004 (2)0.015 (2)
C10.067 (5)0.060 (5)0.076 (5)0.004 (4)−0.002 (4)−0.033 (4)
C20.049 (4)0.069 (5)0.069 (4)0.005 (3)−0.006 (3)−0.024 (4)
C30.039 (4)0.043 (4)0.053 (4)−0.004 (3)−0.003 (3)0.004 (3)
C40.067 (5)0.055 (4)0.086 (5)0.010 (3)−0.026 (4)−0.021 (4)
C50.053 (5)0.087 (6)0.128 (7)0.015 (4)−0.019 (5)−0.041 (5)
C60.060 (5)0.060 (5)0.100 (6)0.007 (4)0.001 (4)−0.022 (4)
C70.131 (8)0.134 (9)0.199 (10)0.032 (7)−0.020 (7)−0.118 (8)
C80.040 (3)0.041 (3)0.046 (3)−0.006 (3)−0.006 (3)−0.003 (3)
C90.046 (4)0.049 (4)0.050 (4)−0.009 (3)−0.010 (3)0.003 (3)
C100.048 (4)0.056 (4)0.063 (4)0.000 (3)−0.006 (3)0.001 (3)
C110.039 (4)0.094 (6)0.096 (5)−0.001 (4)0.007 (4)−0.028 (4)
C120.066 (5)0.091 (5)0.047 (4)0.002 (4)0.013 (4)−0.020 (3)
C130.049 (4)0.052 (4)0.042 (3)0.005 (3)−0.003 (3)−0.003 (3)
C140.045 (3)0.054 (4)0.054 (4)−0.003 (3)0.000 (3)−0.009 (3)
C150.075 (5)0.069 (5)0.056 (4)−0.006 (4)−0.003 (4)−0.001 (3)
C160.076 (5)0.059 (4)0.069 (4)−0.008 (4)−0.015 (4)−0.018 (3)
N20.084 (5)0.095 (5)0.096 (5)0.024 (4)0.031 (4)−0.005 (4)
O30.096 (4)0.068 (4)0.083 (3)−0.018 (3)0.003 (3)−0.010 (3)
O40.051 (3)0.085 (3)0.072 (3)−0.010 (2)0.011 (2)−0.041 (2)
C210.071 (5)0.058 (5)0.051 (4)0.002 (4)0.002 (4)−0.015 (3)
C220.063 (4)0.052 (4)0.051 (4)−0.009 (3)0.004 (3)−0.015 (3)
C230.046 (4)0.065 (5)0.046 (3)0.002 (3)0.009 (3)−0.018 (3)
C240.043 (4)0.088 (6)0.124 (6)0.008 (4)−0.020 (4)−0.026 (5)
C250.068 (5)0.107 (8)0.150 (8)−0.007 (5)−0.020 (5)−0.043 (6)
C260.065 (6)0.074 (6)0.114 (6)−0.019 (4)0.005 (5)−0.033 (5)
C270.139 (7)0.061 (5)0.104 (6)−0.045 (5)0.017 (5)−0.016 (4)
C280.035 (3)0.058 (4)0.056 (4)0.007 (3)−0.007 (3)−0.018 (3)
C290.050 (4)0.087 (5)0.059 (4)−0.013 (3)0.004 (3)−0.024 (4)
C300.041 (4)0.144 (7)0.082 (5)−0.015 (4)0.010 (4)−0.050 (5)
C310.112 (7)0.075 (5)0.083 (6)−0.023 (5)0.032 (5)−0.016 (5)
C320.101 (6)0.082 (6)0.062 (5)−0.029 (5)0.013 (4)−0.018 (4)
C330.046 (4)0.117 (6)0.069 (5)0.017 (4)0.011 (4)0.011 (4)
C340.060 (4)0.071 (5)0.056 (4)−0.001 (3)−0.001 (3)−0.016 (3)
C350.087 (5)0.102 (6)0.075 (5)0.006 (4)0.008 (4)−0.030 (4)
C360.103 (7)0.142 (8)0.100 (6)0.075 (6)−0.008 (5)−0.002 (5)
O50.168 (5)0.059 (3)0.070 (3)0.016 (3)−0.032 (3)−0.008 (3)
O60.059 (3)0.053 (3)0.044 (2)−0.011 (2)−0.0099 (19)−0.007 (2)
O70.049 (3)0.096 (4)0.075 (3)−0.005 (3)−0.007 (2)−0.031 (3)
O80.058 (3)0.071 (3)0.097 (3)−0.006 (2)−0.017 (2)−0.032 (3)
O90.060 (3)0.168 (5)0.082 (3)−0.051 (3)−0.005 (3)0.047 (3)
O100.051 (3)0.116 (4)0.055 (3)−0.008 (2)−0.012 (2)0.006 (3)
O110.050 (2)0.042 (3)0.050 (2)−0.0043 (18)0.0010 (19)0.000 (2)
O120.062 (3)0.091 (4)0.071 (3)0.012 (2)0.010 (2)−0.032 (3)
C410.058 (5)0.050 (4)0.051 (4)−0.003 (3)−0.014 (3)0.005 (3)
C420.044 (4)0.058 (4)0.040 (3)−0.018 (3)−0.004 (3)−0.001 (3)
C430.034 (3)0.056 (4)0.039 (3)−0.011 (3)0.003 (3)−0.001 (3)
C440.030 (3)0.077 (5)0.047 (4)−0.012 (3)0.008 (3)0.001 (3)
C450.066 (5)0.059 (5)0.059 (5)−0.004 (4)−0.007 (4)−0.010 (4)
C460.059 (4)0.069 (5)0.067 (5)−0.019 (4)0.004 (4)−0.015 (4)
C470.131 (7)0.122 (7)0.063 (5)−0.046 (6)−0.002 (5)−0.035 (5)
C480.249 (14)0.141 (10)0.078 (6)−0.078 (9)0.013 (7)−0.053 (6)
C490.167 (10)0.178 (11)0.094 (7)−0.033 (9)0.020 (7)−0.089 (8)
C500.099 (7)0.171 (10)0.150 (9)0.005 (6)−0.010 (7)−0.102 (9)
C510.083 (6)0.105 (7)0.115 (7)0.013 (5)−0.015 (5)−0.062 (6)
C520.041 (4)0.055 (5)0.065 (5)−0.004 (3)−0.009 (3)−0.004 (4)
C530.051 (4)0.058 (5)0.058 (4)−0.004 (3)−0.009 (3)−0.003 (4)
C540.148 (8)0.058 (5)0.058 (5)−0.013 (5)0.017 (5)−0.001 (4)
C550.268 (14)0.073 (7)0.073 (6)−0.043 (7)0.029 (7)−0.004 (5)
C560.229 (13)0.092 (8)0.067 (6)−0.058 (7)−0.018 (7)0.002 (6)
C570.177 (10)0.051 (5)0.114 (7)−0.005 (6)−0.039 (7)0.014 (6)
C580.101 (6)0.070 (6)0.080 (5)−0.004 (4)−0.006 (4)0.005 (4)
O130.121 (4)0.069 (3)0.063 (3)−0.019 (3)−0.004 (3)−0.020 (3)
O140.044 (2)0.048 (3)0.050 (2)0.0049 (19)−0.0105 (18)−0.009 (2)
O150.039 (3)0.085 (3)0.076 (3)0.012 (2)−0.001 (2)0.000 (3)
O160.061 (3)0.055 (3)0.078 (3)0.010 (2)−0.013 (2)0.004 (2)
O170.042 (3)0.118 (4)0.072 (3)0.018 (2)−0.011 (2)−0.037 (3)
O180.049 (3)0.110 (4)0.083 (3)0.011 (2)0.001 (2)−0.052 (3)
O190.046 (2)0.048 (3)0.045 (2)0.0038 (19)0.0048 (18)−0.0151 (19)
O200.063 (3)0.059 (3)0.064 (3)−0.012 (2)0.004 (2)−0.014 (2)
C610.046 (4)0.058 (4)0.046 (4)−0.005 (3)−0.005 (3)−0.013 (3)
C620.043 (4)0.043 (4)0.038 (3)0.009 (3)−0.005 (3)−0.013 (3)
C630.048 (4)0.044 (4)0.039 (3)0.000 (3)0.005 (3)−0.015 (3)
C640.032 (4)0.061 (4)0.058 (4)0.004 (3)0.006 (3)−0.011 (3)
C650.045 (4)0.057 (5)0.059 (4)0.001 (3)0.001 (3)−0.016 (4)
C660.055 (4)0.048 (4)0.063 (4)0.002 (3)0.005 (3)−0.012 (3)
C670.106 (6)0.067 (5)0.081 (5)−0.015 (4)0.002 (5)−0.017 (4)
C680.188 (11)0.065 (6)0.098 (7)−0.015 (6)0.038 (7)−0.005 (6)
C690.228 (12)0.072 (8)0.085 (7)0.009 (7)0.020 (7)0.008 (6)
C700.220 (11)0.086 (7)0.060 (6)0.013 (7)−0.010 (6)−0.007 (5)
C710.120 (7)0.066 (5)0.061 (5)0.005 (4)−0.016 (4)−0.014 (4)
C720.029 (3)0.054 (4)0.063 (4)0.005 (3)−0.009 (3)−0.017 (4)
C730.049 (4)0.070 (5)0.056 (4)0.008 (3)−0.014 (3)−0.027 (4)
C740.069 (5)0.095 (6)0.092 (5)0.000 (4)−0.019 (4)−0.053 (5)
C750.104 (7)0.140 (9)0.143 (8)−0.002 (6)−0.006 (6)−0.105 (8)
C760.114 (8)0.201 (12)0.106 (7)0.014 (8)−0.009 (6)−0.094 (8)
C770.163 (9)0.147 (9)0.062 (5)0.013 (7)0.016 (5)−0.046 (6)
C780.108 (6)0.097 (6)0.055 (4)0.006 (5)0.006 (4)−0.017 (5)

Geometric parameters (Å, °)

N1—C131.486 (6)C35—H35A0.9600
N1—C161.486 (7)C35—H35B0.9600
N1—C121.519 (7)C35—H35C0.9600
N1—H10.8900C36—H36A0.9600
O1—C11.362 (8)C36—H36B0.9600
O1—C71.441 (8)C36—H36C0.9600
O2—C91.422 (6)O5—C451.189 (7)
O2—H2X0.8200O6—C451.339 (7)
C1—C21.357 (8)O6—C421.425 (6)
C1—C61.367 (9)O7—C411.297 (7)
C2—C31.415 (8)O7—H7X0.8200
C2—H20.9300O8—C411.204 (7)
C3—C41.382 (8)O9—C441.228 (6)
C3—C81.533 (8)O10—C441.213 (6)
C4—C51.364 (9)O11—C521.322 (7)
C4—H40.9300O11—C431.433 (6)
C5—C61.357 (9)O12—C521.215 (7)
C5—H50.9300C41—C421.527 (8)
C6—H60.9300C42—C431.513 (7)
C7—H7A0.9600C42—H420.9800
C7—H7B0.9600C43—C441.535 (7)
C7—H7C0.9600C43—H430.9800
C8—C131.513 (7)C45—C461.457 (7)
C8—C141.537 (7)C46—C471.3900
C8—C91.568 (7)C46—C511.3900
C9—C101.516 (7)C47—C481.3900
C9—H90.9800C47—H470.9300
C10—C111.494 (8)C48—C491.3900
C10—H10A0.9700C48—H480.9300
C10—H10B0.9700C49—C501.3900
C11—C121.517 (8)C49—H490.9300
C11—H11A0.9700C50—C511.3900
C11—H11B0.9700C50—H500.9300
C12—H12A0.9700C51—H510.9300
C12—H12B0.9700C52—C531.485 (8)
C13—H13A0.9700C53—C581.365 (8)
C13—H13B0.9700C53—C541.374 (8)
C14—C151.533 (7)C54—C551.382 (10)
C14—H14A0.9700C54—H540.9300
C14—H14B0.9700C55—C561.374 (11)
C15—H15A0.9600C55—H550.9300
C15—H15B0.9600C56—C571.372 (12)
C15—H15C0.9600C56—H560.9300
C16—H16A0.9600C57—C581.389 (10)
C16—H16B0.9600C57—H570.9300
C16—H16C0.9600C58—H580.9300
N2—C331.381 (8)O13—C651.217 (7)
N2—C321.477 (9)O14—C651.328 (7)
N2—C361.533 (9)O14—C621.436 (5)
N2—H2A0.8900O15—C611.277 (7)
O3—C211.358 (7)O15—H150.8200
O3—C271.440 (7)O16—C611.201 (6)
O4—C291.433 (7)O17—C641.260 (7)
O4—H4X0.8200O18—C641.240 (7)
C21—C221.364 (8)O19—C721.332 (6)
C21—C261.369 (9)O19—C631.427 (6)
C22—C231.394 (7)O20—C721.207 (6)
C22—H220.9300C61—C621.544 (7)
C23—C241.407 (8)C62—C631.494 (7)
C23—C281.525 (8)C62—H620.9800
C24—C251.377 (10)C63—C641.527 (7)
C24—H240.9300C63—H630.9800
C25—C261.362 (10)C65—C661.467 (8)
C25—H250.9300C66—C671.370 (8)
C26—H260.9300C66—C711.391 (9)
C27—H27A0.9600C67—C681.389 (10)
C27—H27B0.9600C67—H670.9300
C27—H27C0.9600C68—C691.347 (12)
C28—C341.532 (7)C68—H680.9300
C28—C291.538 (7)C69—C701.381 (12)
C28—C331.550 (8)C69—H690.9300
C29—C301.570 (9)C70—C711.384 (9)
C29—H290.9800C70—H700.9300
C30—C311.515 (9)C71—H710.9300
C30—H30A0.9700C72—C731.482 (7)
C30—H30B0.9700C73—C741.3900
C31—C321.440 (10)C73—C781.3900
C31—H31A0.9700C74—C751.3900
C31—H31B0.9700C74—H740.9300
C32—H32A0.9700C75—C761.3900
C32—H32B0.9700C75—H750.9300
C33—H33A0.9700C76—C771.3900
C33—H33B0.9700C76—H760.9300
C34—C351.512 (8)C77—C781.3900
C34—H34A0.9700C77—H770.9300
C34—H34B0.9700C78—H780.9300
C13—N1—C16109.8 (5)N2—C33—H33A107.1
C13—N1—C12113.8 (4)C28—C33—H33A107.1
C16—N1—C12110.1 (4)N2—C33—H33B107.1
C13—N1—H1107.6C28—C33—H33B107.1
C16—N1—H1107.6H33A—C33—H33B106.8
C12—N1—H1107.6C35—C34—C28116.9 (5)
C1—O1—C7119.4 (6)C35—C34—H34A108.1
C9—O2—H2X109.5C28—C34—H34A108.1
C2—C1—O1114.1 (6)C35—C34—H34B108.1
C2—C1—C6122.2 (7)C28—C34—H34B108.1
O1—C1—C6123.8 (6)H34A—C34—H34B107.3
C1—C2—C3121.3 (6)C34—C35—H35A109.5
C1—C2—H2119.4C34—C35—H35B109.5
C3—C2—H2119.4H35A—C35—H35B109.5
C4—C3—C2115.2 (6)C34—C35—H35C109.5
C4—C3—C8124.6 (6)H35A—C35—H35C109.5
C2—C3—C8120.1 (5)H35B—C35—H35C109.5
C5—C4—C3121.8 (7)N2—C36—H36A109.5
C5—C4—H4119.1N2—C36—H36B109.5
C3—C4—H4119.1H36A—C36—H36B109.5
C6—C5—C4122.4 (7)N2—C36—H36C109.5
C6—C5—H5118.8H36A—C36—H36C109.5
C4—C5—H5118.8H36B—C36—H36C109.5
C5—C6—C1117.0 (6)C45—O6—C42117.6 (4)
C5—C6—H6121.5C41—O7—H7X109.5
C1—C6—H6121.5C52—O11—C43116.6 (4)
O1—C7—H7A109.5O8—C41—O7126.5 (6)
O1—C7—H7B109.5O8—C41—C42119.8 (6)
H7A—C7—H7B109.5O7—C41—C42113.7 (6)
O1—C7—H7C109.5O6—C42—C43108.3 (4)
H7A—C7—H7C109.5O6—C42—C41112.5 (5)
H7B—C7—H7C109.5C43—C42—C41110.5 (5)
C13—C8—C3107.9 (4)O6—C42—H42108.5
C13—C8—C14111.6 (4)C43—C42—H42108.5
C3—C8—C14109.6 (4)C41—C42—H42108.5
C13—C8—C9112.0 (4)O11—C43—C42106.1 (4)
C3—C8—C9106.8 (4)O11—C43—C44111.8 (4)
C14—C8—C9108.8 (4)C42—C43—C44114.0 (5)
O2—C9—C10111.2 (4)O11—C43—H43108.3
O2—C9—C8106.6 (4)C42—C43—H43108.3
C10—C9—C8116.4 (5)C44—C43—H43108.3
O2—C9—H9107.4O10—C44—O9126.9 (6)
C10—C9—H9107.4O10—C44—C43119.7 (5)
C8—C9—H9107.4O9—C44—C43113.4 (5)
C11—C10—C9121.7 (5)O5—C45—O6124.2 (6)
C11—C10—H10A106.9O5—C45—C46123.8 (6)
C9—C10—H10A106.9O6—C45—C46111.9 (6)
C11—C10—H10B106.9C47—C46—C51120.0
C9—C10—H10B106.9C47—C46—C45122.0 (5)
H10A—C10—H10B106.7C51—C46—C45117.9 (5)
C10—C11—C12118.0 (5)C48—C47—C46120.0
C10—C11—H11A107.8C48—C47—H47120.0
C12—C11—H11A107.8C46—C47—H47120.0
C10—C11—H11B107.8C47—C48—C49120.0
C12—C11—H11B107.8C47—C48—H48120.0
H11A—C11—H11B107.1C49—C48—H48120.0
C11—C12—N1113.6 (5)C50—C49—C48120.0
C11—C12—H12A108.8C50—C49—H49120.0
N1—C12—H12A108.8C48—C49—H49120.0
C11—C12—H12B108.8C49—C50—C51120.0
N1—C12—H12B108.8C49—C50—H50120.0
H12A—C12—H12B107.7C51—C50—H50120.0
N1—C13—C8118.2 (5)C50—C51—C46120.0
N1—C13—H13A107.8C50—C51—H51120.0
C8—C13—H13A107.8C46—C51—H51120.0
N1—C13—H13B107.8O12—C52—O11123.9 (6)
C8—C13—H13B107.8O12—C52—C53122.6 (6)
H13A—C13—H13B107.1O11—C52—C53113.5 (6)
C15—C14—C8116.2 (5)C58—C53—C54119.7 (6)
C15—C14—H14A108.2C58—C53—C52119.9 (6)
C8—C14—H14A108.2C54—C53—C52120.4 (6)
C15—C14—H14B108.2C53—C54—C55119.9 (8)
C8—C14—H14B108.2C53—C54—H54120.1
H14A—C14—H14B107.4C55—C54—H54120.1
C14—C15—H15A109.5C56—C55—C54120.0 (9)
C14—C15—H15B109.5C56—C55—H55120.0
H15A—C15—H15B109.5C54—C55—H55120.0
C14—C15—H15C109.5C57—C56—C55120.6 (8)
H15A—C15—H15C109.5C57—C56—H56119.7
H15B—C15—H15C109.5C55—C56—H56119.7
N1—C16—H16A109.5C56—C57—C58118.8 (8)
N1—C16—H16B109.5C56—C57—H57120.6
H16A—C16—H16B109.5C58—C57—H57120.6
N1—C16—H16C109.5C53—C58—C57121.0 (8)
H16A—C16—H16C109.5C53—C58—H58119.5
H16B—C16—H16C109.5C57—C58—H58119.5
C33—N2—C32118.9 (7)C65—O14—C62118.4 (4)
C33—N2—C36111.5 (5)C61—O15—H15109.5
C32—N2—C36108.3 (6)C72—O19—C63117.0 (4)
C33—N2—H2A105.7O16—C61—O15128.4 (6)
C32—N2—H2A105.7O16—C61—C62119.4 (6)
C36—N2—H2A105.7O15—C61—C62112.2 (5)
C21—O3—C27121.2 (6)O14—C62—C63107.0 (4)
C29—O4—H4X109.5O14—C62—C61111.7 (4)
O3—C21—C22115.3 (7)C63—C62—C61109.7 (4)
O3—C21—C26123.7 (7)O14—C62—H62109.5
C22—C21—C26121.0 (7)C63—C62—H62109.5
C21—C22—C23121.9 (6)C61—C62—H62109.5
C21—C22—H22119.1O19—C63—C62107.6 (4)
C23—C22—H22119.1O19—C63—C64110.7 (4)
C22—C23—C24116.7 (6)C62—C63—C64113.0 (4)
C22—C23—C28120.7 (5)O19—C63—H63108.5
C24—C23—C28122.6 (6)C62—C63—H63108.5
C25—C24—C23119.7 (7)C64—C63—H63108.5
C25—C24—H24120.1O18—C64—O17125.7 (5)
C23—C24—H24120.1O18—C64—C63116.1 (6)
C26—C25—C24122.3 (8)O17—C64—C63118.2 (5)
C26—C25—H25118.9O13—C65—O14123.4 (6)
C24—C25—H25118.9O13—C65—C66125.0 (7)
C25—C26—C21118.3 (7)O14—C65—C66111.6 (6)
C25—C26—H26120.8C67—C66—C71118.9 (6)
C21—C26—H26120.8C67—C66—C65119.7 (6)
O3—C27—H27A109.5C71—C66—C65121.4 (6)
O3—C27—H27B109.5C66—C67—C68122.0 (8)
H27A—C27—H27B109.5C66—C67—H67119.0
O3—C27—H27C109.5C68—C67—H67119.0
H27A—C27—H27C109.5C69—C68—C67118.0 (9)
H27B—C27—H27C109.5C69—C68—H68121.0
C23—C28—C34109.4 (5)C67—C68—H68121.0
C23—C28—C29108.5 (4)C68—C69—C70121.8 (9)
C34—C28—C29108.2 (4)C68—C69—H69119.1
C23—C28—C33113.9 (5)C70—C69—H69119.1
C34—C28—C33105.0 (5)C69—C70—C71119.6 (9)
C29—C28—C33111.7 (5)C69—C70—H70120.2
O4—C29—C28106.9 (5)C71—C70—H70120.2
O4—C29—C30108.9 (5)C70—C71—C66119.3 (8)
C28—C29—C30114.8 (5)C70—C71—H71120.4
O4—C29—H29108.7C66—C71—H71120.4
C28—C29—H29108.7O20—C72—O19123.4 (5)
C30—C29—H29108.7O20—C72—C73124.1 (6)
C31—C30—C29114.2 (6)O19—C72—C73112.4 (5)
C31—C30—H30A108.7C74—C73—C78120.0
C29—C30—H30A108.7C74—C73—C72118.1 (4)
C31—C30—H30B108.7C78—C73—C72121.8 (4)
C29—C30—H30B108.7C73—C74—C75120.0
H30A—C30—H30B107.6C73—C74—H74120.0
C32—C31—C30121.0 (6)C75—C74—H74120.0
C32—C31—H31A107.1C76—C75—C74120.0
C30—C31—H31A107.1C76—C75—H75120.0
C32—C31—H31B107.1C74—C75—H75120.0
C30—C31—H31B107.1C75—C76—C77120.0
H31A—C31—H31B106.8C75—C76—H76120.0
C31—C32—N2115.7 (6)C77—C76—H76120.0
C31—C32—H32A108.3C78—C77—C76120.0
N2—C32—H32A108.3C78—C77—H77120.0
C31—C32—H32B108.3C76—C77—H77120.0
N2—C32—H32B108.3C77—C78—C73120.0
H32A—C32—H32B107.4C77—C78—H78120.0
N2—C33—C28121.1 (6)C73—C78—H78120.0
C7—O1—C1—C2177.4 (7)C52—O11—C43—C42−144.4 (4)
C7—O1—C1—C6−1.9 (11)C52—O11—C43—C4490.8 (6)
O1—C1—C2—C3−177.4 (5)O6—C42—C43—O11−63.9 (5)
C6—C1—C2—C31.9 (10)C41—C42—C43—O1159.8 (5)
C1—C2—C3—C4−1.1 (9)O6—C42—C43—C4459.6 (5)
C1—C2—C3—C8−179.9 (6)C41—C42—C43—C44−176.8 (5)
C2—C3—C4—C5−1.4 (9)O11—C43—C44—O102.5 (8)
C8—C3—C4—C5177.3 (6)C42—C43—C44—O10−117.9 (6)
C3—C4—C5—C63.3 (11)O11—C43—C44—O9−176.6 (5)
C4—C5—C6—C1−2.5 (11)C42—C43—C44—O963.1 (7)
C2—C1—C6—C5−0.1 (10)C42—O6—C45—O53.6 (9)
O1—C1—C6—C5179.1 (7)C42—O6—C45—C46−174.8 (5)
C4—C3—C8—C13−6.4 (7)O5—C45—C46—C47174.8 (6)
C2—C3—C8—C13172.3 (5)O6—C45—C46—C47−6.8 (7)
C4—C3—C8—C14−128.1 (6)O5—C45—C46—C51−2.7 (9)
C2—C3—C8—C1450.6 (7)O6—C45—C46—C51175.7 (4)
C4—C3—C8—C9114.1 (6)C51—C46—C47—C480.0
C2—C3—C8—C9−67.2 (6)C45—C46—C47—C48−177.5 (5)
C13—C8—C9—O247.5 (6)C46—C47—C48—C490.0
C3—C8—C9—O2−70.3 (5)C47—C48—C49—C500.0
C14—C8—C9—O2171.4 (4)C48—C49—C50—C510.0
C13—C8—C9—C10−77.2 (6)C49—C50—C51—C460.0
C3—C8—C9—C10165.0 (5)C47—C46—C51—C500.0
C14—C8—C9—C1046.7 (6)C45—C46—C51—C50177.6 (5)
O2—C9—C10—C11−68.5 (7)C43—O11—C52—O120.0 (8)
C8—C9—C10—C1153.9 (8)C43—O11—C52—C53178.8 (4)
C9—C10—C11—C1212.2 (9)O12—C52—C53—C58−7.7 (9)
C10—C11—C12—N1−71.1 (8)O11—C52—C53—C58173.5 (6)
C13—N1—C12—C1181.3 (6)O12—C52—C53—C54172.0 (7)
C16—N1—C12—C11−154.9 (5)O11—C52—C53—C54−6.8 (8)
C16—N1—C13—C8169.6 (4)C58—C53—C54—C550.8 (12)
C12—N1—C13—C8−66.4 (6)C52—C53—C54—C55−179.0 (8)
C3—C8—C13—N1−176.4 (4)C53—C54—C55—C56−1.7 (15)
C14—C8—C13—N1−55.9 (6)C54—C55—C56—C571.2 (17)
C9—C8—C13—N166.4 (6)C55—C56—C57—C580.1 (16)
C13—C8—C14—C15−59.7 (6)C54—C53—C58—C570.6 (11)
C3—C8—C14—C1559.8 (6)C52—C53—C58—C57−179.7 (7)
C9—C8—C14—C15176.2 (5)C56—C57—C58—C53−1.0 (14)
C27—O3—C21—C22−178.5 (5)C65—O14—C62—C63−152.1 (4)
C27—O3—C21—C263.4 (9)C65—O14—C62—C6187.8 (5)
O3—C21—C22—C23−178.5 (5)O16—C61—C62—O14155.2 (5)
C26—C21—C22—C23−0.3 (9)O15—C61—C62—O14−25.7 (7)
C21—C22—C23—C240.2 (8)O16—C61—C62—C6336.7 (7)
C21—C22—C23—C28179.4 (5)O15—C61—C62—C63−144.1 (5)
C22—C23—C24—C251.8 (10)C72—O19—C63—C62−152.4 (4)
C28—C23—C24—C25−177.4 (7)C72—O19—C63—C6483.7 (5)
C23—C24—C25—C26−3.7 (13)O14—C62—C63—O19−60.9 (5)
C24—C25—C26—C213.6 (12)C61—C62—C63—O1960.4 (5)
O3—C21—C26—C25176.5 (7)O14—C62—C63—C6461.7 (5)
C22—C21—C26—C25−1.5 (10)C61—C62—C63—C64−177.0 (5)
C22—C23—C28—C3449.4 (6)O19—C63—C64—O18177.0 (5)
C24—C23—C28—C34−131.5 (6)C62—C63—C64—O1856.2 (7)
C22—C23—C28—C29−68.5 (6)O19—C63—C64—O17−3.3 (7)
C24—C23—C28—C29110.7 (6)C62—C63—C64—O17−124.1 (5)
C22—C23—C28—C33166.5 (5)C62—O14—C65—O138.2 (8)
C24—C23—C28—C33−14.4 (8)C62—O14—C65—C66−173.1 (4)
C23—C28—C29—O4−52.6 (6)O13—C65—C66—C67−7.2 (9)
C34—C28—C29—O4−171.2 (5)O14—C65—C66—C67174.0 (5)
C33—C28—C29—O473.7 (6)O13—C65—C66—C71171.5 (6)
C23—C28—C29—C30−173.5 (6)O14—C65—C66—C71−7.2 (8)
C34—C28—C29—C3067.9 (7)C71—C66—C67—C682.4 (11)
C33—C28—C29—C30−47.1 (7)C65—C66—C67—C68−178.8 (7)
O4—C29—C30—C31−36.0 (7)C66—C67—C68—C690.3 (14)
C28—C29—C30—C3183.8 (7)C67—C68—C69—C70−5.1 (16)
C29—C30—C31—C32−61.7 (9)C68—C69—C70—C717.0 (16)
C30—C31—C32—N244.2 (10)C69—C70—C71—C66−4.1 (13)
C33—N2—C32—C31−67.6 (9)C67—C66—C71—C70−0.4 (10)
C36—N2—C32—C31163.7 (7)C65—C66—C71—C70−179.2 (7)
C32—N2—C33—C2884.7 (9)C63—O19—C72—O200.4 (7)
C36—N2—C33—C28−148.2 (7)C63—O19—C72—C73178.3 (4)
C23—C28—C33—N294.8 (7)O20—C72—C73—C743.3 (7)
C34—C28—C33—N2−145.6 (7)O19—C72—C73—C74−174.6 (3)
C29—C28—C33—N2−28.6 (9)O20—C72—C73—C78−179.2 (4)
C23—C28—C34—C3561.2 (7)O19—C72—C73—C782.9 (6)
C29—C28—C34—C35179.3 (5)C78—C73—C74—C750.0
C33—C28—C34—C35−61.4 (7)C72—C73—C74—C75177.6 (4)
C45—O6—C42—C43−141.2 (5)C73—C74—C75—C760.0
C45—O6—C42—C4196.4 (6)C74—C75—C76—C770.0
O8—C41—C42—O6160.0 (5)C75—C76—C77—C780.0
O7—C41—C42—O6−21.0 (7)C76—C77—C78—C730.0
O8—C41—C42—C4338.8 (7)C74—C73—C78—C770.0
O7—C41—C42—C43−142.2 (5)C72—C73—C78—C77−177.5 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O160.891.902.719 (6)151
N2—H2A···O40.892.242.884 (7)129
O2—H2X···O9i0.822.182.779 (6)130
O4—H4X···O18ii0.822.122.819 (6)143
O7—H7X···O9iii0.822.533.339 (6)170
O7—H7X···O10iii0.821.912.470 (6)124
O15—H15···O17ii0.821.622.435 (5)170

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2195).

References

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  • Hao, J. L., Li, W., Xie, Q., Chen, Y. & Qiu, Z. B. (2005). J. Fudan. University. (Med. Sci.), 32, 173–177.
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