organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aDepartment of Medicinal Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, People's Republic of China
*Correspondence e-mail: zbqiu@shmu.edu.cn

(Received 10 March 2010; accepted 12 April 2010; online 17 April 2010)

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[Hao, J. L., Li, W., Xie, Q., Chen, Y. & Qiu, Z. B. (2005). J. Fudan. University. (Med. Sci.), 32, 173-177.]). For conformational studies of seven-membered rings, see: Eliel et al. (1994[Eliel, E. L., Wilen, S. H. & Mander, L. N. (1994). Stereochemistry of Organic Compounds, pp. 762-769. New York: Wiley.]); Entrena et al. (2005[Entrena, A., Campos, J. M., Gallo, M. A. E. & Spinosa, A. (2005). Arkivoc, 6, 88-108.]). For a related structure, see: Wang et al. (2008[Wang, X.-H., Chao, B. & Qiu, Z.-B. (2008). Acta Cryst. E64, o784.]).

[Scheme 1]

Experimental

Crystal data
  • C16H26NO2+·C18H13O8

  • Mr = 621.66

  • Triclinic, P 1

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.977, Tmax = 0.991

  • 8191 measured reflections

  • 5753 independent reflections

  • 2826 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O16 0.89 1.90 2.719 (6) 151
N2—H2A⋯O4 0.89 2.24 2.884 (7) 129
O2—H2X⋯O9i 0.82 2.18 2.779 (6) 130
O4—H4X⋯O18ii 0.82 2.12 2.819 (6) 143
O7—H7X⋯O9iii 0.82 2.53 3.339 (6) 170
O7—H7X⋯O10iii 0.82 1.91 2.470 (6) 124
O15—H15⋯O17ii 0.82 1.62 2.435 (5) 170
Symmetry codes: (i) x, y+1, z-1; (ii) x-1, y, z; (iii) x+1, y, z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconisin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconisin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Structure description top

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.

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

Computing details top

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

Figures top
[Figure 1] 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.
(3S,4R)-3-ethyl-4-hydroxy-3-(3-methoxyphenyl)-1-methylazepanium (2R,3R)-2,3-bis(benzoyloxy)-3-carboxypropionate top
Crystal data top
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 top
Bruker SMART APEX CCD area-detector
diffractometer
5753 independent reflections
Radiation source: fine-focus sealed tube2826 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scansθmax = 25.2°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.977, Tmax = 0.991k = 1617
8191 measured reflectionsl = 1817
Refinement top
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 = 0.80 w = 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
Crystal data top
C16H26NO2+·C18H13O8γ = 88.367 (6)°
Mr = 621.66V = 1638.0 (11) Å3
Triclinic, P1Z = 2
a = 7.772 (3) ÅMo Kα radiation
b = 14.603 (6) ŵ = 0.09 mm1
c = 15.060 (6) ÅT = 295 K
α = 75.313 (6)°0.25 × 0.15 × 0.10 mm
β = 82.182 (6)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5753 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2826 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.991Rint = 0.034
8191 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04816 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 0.80Δρmax = 0.19 e Å3
5753 reflectionsΔρmin = 0.19 e Å3
795 parameters
Special details top

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) top
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)
H2X0.28821.08970.00420.102*
C10.0586 (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)
C40.1594 (9)1.0219 (4)0.1656 (4)0.0673 (18)
H40.19610.99260.12330.081*
C50.2679 (9)1.0837 (5)0.1996 (6)0.087 (2)
H50.37871.09250.18220.104*
C60.2200 (9)1.1326 (5)0.2579 (5)0.074 (2)
H60.29381.17620.27880.089*
C70.0919 (13)1.2314 (6)0.3748 (7)0.141 (4)
H7A0.09791.28640.32440.212*
H7B0.03751.24790.42220.212*
H7C0.20711.20790.39980.212*
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*
H11B0.54320.85560.01030.092*
C120.2830 (8)0.8353 (5)0.0022 (4)0.0695 (19)
H12A0.30690.78910.03850.083*
H12B0.25470.89450.04380.083*
C130.0350 (7)0.8796 (4)0.1046 (4)0.0497 (15)
H13A0.07190.85350.14270.060*
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)
H15A0.03620.84380.33540.104*
H15B0.10020.76530.36710.104*
H15C0.00510.76080.28650.104*
C160.0031 (8)0.7502 (4)0.0333 (4)0.0673 (18)
H16A0.09410.72850.08000.101*
H16B0.06050.69690.01630.101*
H16C0.03690.79160.02010.101*
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)
H220.21240.65810.18990.067*
C230.3720 (7)0.5635 (4)0.1202 (4)0.0527 (16)
C240.5353 (8)0.5589 (5)0.0888 (5)0.084 (2)
H240.57760.50100.05790.101*
C250.6320 (11)0.6402 (7)0.1041 (7)0.106 (3)
H250.73650.63680.07980.127*
C260.5800 (10)0.7256 (6)0.1535 (6)0.084 (2)
H260.65030.77900.16590.101*
C270.4469 (11)0.9008 (5)0.2537 (5)0.104 (3)
H27A0.47470.91450.19830.157*
H27B0.37710.95080.28500.157*
H27C0.55210.89570.29360.157*
C280.2545 (7)0.4771 (4)0.1023 (4)0.0492 (15)
C290.0952 (8)0.4885 (5)0.0333 (4)0.0651 (18)
H290.02840.54320.06240.078*
C300.0287 (8)0.3998 (6)0.0010 (5)0.087 (2)
H30A0.14440.42080.01970.104*
H30B0.03500.37190.05040.104*
C310.0271 (11)0.3245 (5)0.0811 (5)0.095 (3)
H31A0.02700.35330.13240.114*
H31B0.06290.27610.09960.114*
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)
H33A0.30120.33690.09780.103*
H33B0.46880.39110.09440.103*
C340.1910 (8)0.4722 (4)0.1929 (4)0.0628 (18)
H34A0.11130.41910.17940.075*
H34B0.12550.52920.21460.075*
C350.3281 (9)0.4621 (5)0.2713 (4)0.088 (2)
H35A0.42060.50660.27780.133*
H35B0.27750.47450.32780.133*
H35C0.37330.39900.25790.133*
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)
H490.92480.15320.50400.167*
C500.9603 (7)0.1850 (4)0.6389 (5)0.130 (4)
H500.98130.24920.64510.156*
C510.9627 (6)0.1466 (4)0.7143 (4)0.095 (3)
H510.98530.18510.77090.114*
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) top
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, º) top
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—C42144.4 (4)
C7—O1—C1—C61.9 (11)C52—O11—C43—C4490.8 (6)
O1—C1—C2—C3177.4 (5)O6—C42—C43—O1163.9 (5)
C6—C1—C2—C31.9 (10)C41—C42—C43—O1159.8 (5)
C1—C2—C3—C41.1 (9)O6—C42—C43—C4459.6 (5)
C1—C2—C3—C8179.9 (6)C41—C42—C43—C44176.8 (5)
C2—C3—C4—C51.4 (9)O11—C43—C44—O102.5 (8)
C8—C3—C4—C5177.3 (6)C42—C43—C44—O10117.9 (6)
C3—C4—C5—C63.3 (11)O11—C43—C44—O9176.6 (5)
C4—C5—C6—C12.5 (11)C42—C43—C44—O963.1 (7)
C2—C1—C6—C50.1 (10)C42—O6—C45—O53.6 (9)
O1—C1—C6—C5179.1 (7)C42—O6—C45—C46174.8 (5)
C4—C3—C8—C136.4 (7)O5—C45—C46—C47174.8 (6)
C2—C3—C8—C13172.3 (5)O6—C45—C46—C476.8 (7)
C4—C3—C8—C14128.1 (6)O5—C45—C46—C512.7 (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—C967.2 (6)C45—C46—C47—C48177.5 (5)
C13—C8—C9—O247.5 (6)C46—C47—C48—C490.0
C3—C8—C9—O270.3 (5)C47—C48—C49—C500.0
C14—C8—C9—O2171.4 (4)C48—C49—C50—C510.0
C13—C8—C9—C1077.2 (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—C1168.5 (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—C587.7 (9)
C10—C11—C12—N171.1 (8)O11—C52—C53—C58173.5 (6)
C13—N1—C12—C1181.3 (6)O12—C52—C53—C54172.0 (7)
C16—N1—C12—C11154.9 (5)O11—C52—C53—C546.8 (8)
C16—N1—C13—C8169.6 (4)C58—C53—C54—C550.8 (12)
C12—N1—C13—C866.4 (6)C52—C53—C54—C55179.0 (8)
C3—C8—C13—N1176.4 (4)C53—C54—C55—C561.7 (15)
C14—C8—C13—N155.9 (6)C54—C55—C56—C571.2 (17)
C9—C8—C13—N166.4 (6)C55—C56—C57—C580.1 (16)
C13—C8—C14—C1559.7 (6)C54—C53—C58—C570.6 (11)
C3—C8—C14—C1559.8 (6)C52—C53—C58—C57179.7 (7)
C9—C8—C14—C15176.2 (5)C56—C57—C58—C531.0 (14)
C27—O3—C21—C22178.5 (5)C65—O14—C62—C63152.1 (4)
C27—O3—C21—C263.4 (9)C65—O14—C62—C6187.8 (5)
O3—C21—C22—C23178.5 (5)O16—C61—C62—O14155.2 (5)
C26—C21—C22—C230.3 (9)O15—C61—C62—O1425.7 (7)
C21—C22—C23—C240.2 (8)O16—C61—C62—C6336.7 (7)
C21—C22—C23—C28179.4 (5)O15—C61—C62—C63144.1 (5)
C22—C23—C24—C251.8 (10)C72—O19—C63—C62152.4 (4)
C28—C23—C24—C25177.4 (7)C72—O19—C63—C6483.7 (5)
C23—C24—C25—C263.7 (13)O14—C62—C63—O1960.9 (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—C251.5 (10)C61—C62—C63—C64177.0 (5)
C22—C23—C28—C3449.4 (6)O19—C63—C64—O18177.0 (5)
C24—C23—C28—C34131.5 (6)C62—C63—C64—O1856.2 (7)
C22—C23—C28—C2968.5 (6)O19—C63—C64—O173.3 (7)
C24—C23—C28—C29110.7 (6)C62—C63—C64—O17124.1 (5)
C22—C23—C28—C33166.5 (5)C62—O14—C65—O138.2 (8)
C24—C23—C28—C3314.4 (8)C62—O14—C65—C66173.1 (4)
C23—C28—C29—O452.6 (6)O13—C65—C66—C677.2 (9)
C34—C28—C29—O4171.2 (5)O14—C65—C66—C67174.0 (5)
C33—C28—C29—O473.7 (6)O13—C65—C66—C71171.5 (6)
C23—C28—C29—C30173.5 (6)O14—C65—C66—C717.2 (8)
C34—C28—C29—C3067.9 (7)C71—C66—C67—C682.4 (11)
C33—C28—C29—C3047.1 (7)C65—C66—C67—C68178.8 (7)
O4—C29—C30—C3136.0 (7)C66—C67—C68—C690.3 (14)
C28—C29—C30—C3183.8 (7)C67—C68—C69—C705.1 (16)
C29—C30—C31—C3261.7 (9)C68—C69—C70—C717.0 (16)
C30—C31—C32—N244.2 (10)C69—C70—C71—C664.1 (13)
C33—N2—C32—C3167.6 (9)C67—C66—C71—C700.4 (10)
C36—N2—C32—C31163.7 (7)C65—C66—C71—C70179.2 (7)
C32—N2—C33—C2884.7 (9)C63—O19—C72—O200.4 (7)
C36—N2—C33—C28148.2 (7)C63—O19—C72—C73178.3 (4)
C23—C28—C33—N294.8 (7)O20—C72—C73—C743.3 (7)
C34—C28—C33—N2145.6 (7)O19—C72—C73—C74174.6 (3)
C29—C28—C33—N228.6 (9)O20—C72—C73—C78179.2 (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—C3561.4 (7)C72—C73—C74—C75177.6 (4)
C45—O6—C42—C43141.2 (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—O621.0 (7)C76—C77—C78—C730.0
O8—C41—C42—C4338.8 (7)C74—C73—C78—C770.0
O7—C41—C42—C43142.2 (5)C72—C73—C78—C77177.5 (4)
Hydrogen-bond geometry (Å, º) top
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, z1; (ii) x1, y, z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC16H26NO2+·C18H13O8
Mr621.66
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)7.772 (3), 14.603 (6), 15.060 (6)
α, β, γ (°)75.313 (6), 82.182 (6), 88.367 (6)
V3)1638.0 (11)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.25 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.977, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
8191, 5753, 2826
Rint0.034
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.110, 0.80
No. of reflections5753
No. of parameters795
No. of restraints16
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.19

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O160.891.902.719 (6)151.3
N2—H2A···O40.892.242.884 (7)129.1
O2—H2X···O9i0.822.182.779 (6)129.6
O4—H4X···O18ii0.822.122.819 (6)142.8
O7—H7X···O9iii0.822.533.339 (6)170.3
O7—H7X···O10iii0.821.912.470 (6)124.1
O15—H15···O17ii0.821.622.435 (5)170.2
Symmetry codes: (i) x, y+1, z1; (ii) x1, y, z; (iii) x+1, y, z.
 

Acknowledgements

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

References

First citationBruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconisin, USA.  Google Scholar
First citationEliel, E. L., Wilen, S. H. & Mander, L. N. (1994). Stereochemistry of Organic Compounds, pp. 762–769. New York: Wiley.  Google Scholar
First citationEntrena, A., Campos, J. M., Gallo, M. A. E. & Spinosa, A. (2005). Arkivoc, 6, 88–108.  CrossRef Google Scholar
First citationHao, J. L., Li, W., Xie, Q., Chen, Y. & Qiu, Z. B. (2005). J. Fudan. University. (Med. Sci.), 32, 173–177.  CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, X.-H., Chao, B. & Qiu, Z.-B. (2008). Acta Cryst. E64, o784.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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