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ISSN: 2056-9890

Crystal structure of natural phaeosphaeride A

aChemical Modeling Laboratory, Research Institute of Hygiene, Occupational Pathology and Human Ecology, Medical Biological Agency, p/o Kuz'molovsky, Saint Petersburg, 188663, Russian Federation, bAll-Russian Institute of Plant Protection, Russian Academy of Agricultural Sciences, Pushkin, Saint Petersburg, 196608, Russian Federation, cDepartment of Crystallography, Institute of Earth Sciences, Saint Petersburg State University, University Emb., 7/9, Saint Petersburg, 199034, Russian Federation, and dDepartment of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, University Emb., 26, Saint Petersburg, 198504, Russian Federation
*Correspondence e-mail: vvaavv@mail.ru, aberestetski@yahoo.com

Edited by S. Parkin, University of Kentucky, USA (Received 14 July 2015; accepted 22 July 2015; online 31 July 2015)

The asymmetric unit of the title compound, C15H23NO5, contains two independent mol­ecules. Phaeosphaeride A contains two primary sections, an alkyl chain consisting of five C atoms and a cyclic system consisting of fused five- and six-membered rings with attached substituents. In the crystal, the mol­ecules form layered structures. Nearly planar sheets, parallel to the (001) plane, form bilayers of two-dimensional hydrogen-bonded networks with the hy­droxy groups located on the inter­ior of the bilayer sheets. The network is constructed primarily of four O—H⋯O hydrogen bonds, which form a zigzag pattern in the (001) plane. The butyl chains inter­digitate with the butyl chains on adjacent sheets. The crystal was twinned by a twofold rotation about the c axis, with refined major–minor occupancy fractions of 0.718 (6):0.282 (6).

1. Related literature

For details of the extraction of natural phaeosphaeride A and a discussion of its biological activities, see: Maloney et al. (2006[Maloney, K. N., Hao, W., Xu, J., Gibbons, J., Hucul, J., Roll, D., Brady, S. F., Schroeder, F. C. & Clardy, J. (2006). Org. Lett. 8, 4067-4070.]). For details of trials of the synthesis of natural phaeosphaeride A, see: Kobayashi et al. (2011[Kobayashi, K., Okamoto, I., Morita, N., Kiyotani, T. & Tamura, O. (2011). Org. Biomol. Chem. 9, 5825-5832.]); Chatzimpaloglou et al. (2012[Chatzimpaloglou, A., Yavropoulou, M. P., Rooij, K. E., Biedermann, R., Mueller, U., Kaskel, S. & Sarli, V. (2012). J. Org. Chem. 77, 9659-9667.], 2014[Chatzimpaloglou, A., Kolosov, M., Eckols, T. K., Tweardy, D. J. & Sarli, V. (2014). J. Org. Chem. 79, 4043-4054.]); Kobayashi et al. (2015[Kobayashi, K., Kobayashi, Y., Nakamura, M., Tamura, O. & Kogen, H. (2015). J. Org. Chem. 80, 1243-1248.]). Ring-puckering parameters are as defined by Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). Hydrogen bonding is described in detail by Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). In The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press Inc.]) and by Arunan et al. (2011[Arunan, E., Desiraju, G. R., Klein, R. A., Sadley, J., Scheiner, S., Alcorta, I., Clary, D. C., Crabtree, R. H., Dannenberg, J. J., Hobza, P., Kjaergaard, H. G., Legon, A. C., Menucci, B. & Nesbitt, D. J. (2011). Pure Appl. Chem. 83, 1637-1641.]). The twin law was identified using TwinRotMat in PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). Criteria for absolute configuration determination are described by Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]) and Parsons et al. (2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C15H23NO5

  • Mr = 297.34

  • Monoclinic, P 21

  • a = 10.14078 (18) Å

  • b = 9.10361 (14) Å

  • c = 17.5991 (3) Å

  • β = 100.1847 (16)°

  • V = 1599.11 (5) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.77 mm−1

  • T = 100 K

  • 0.35 × 0.35 × 0.05 mm

2.2. Data collection

  • Agilent SuperNova Dual Source diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.824, Tmax = 1.000

  • 6054 measured reflections

  • 6054 independent reflections

  • 5940 reflections with I > 2σ(I)

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.150

  • S = 1.10

  • 6054 reflections

  • 389 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.30 e Å−3

  • Absolute structure: Flack x determined using 2632 quotients [(I+) − (I)]/[(I+) + (I)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])

  • Absolute structure parameter: 0.05 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O2A 0.82 2.04 2.818 (5) 158
O3—H3⋯O4i 0.82 2.03 2.836 (5) 168
O2A—H2A⋯O4i 0.82 2.00 2.685 (5) 141
O3A—H3A⋯O4Aii 0.82 2.10 2.829 (5) 149
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+2]; (ii) [-x+1, y-{\script{1\over 2}}, -z+2].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information


Comment top

In 2006, Clardy and colleagues isolated phaeosphaeride A from an endophytic fungus FA39 (Maloney et al., 2006). Phaeosphaeride A turned out to be an inhibitor of signal transduction and an activator of transcription 3 (STAT3)-dependent signaling. It was reported to selectively inhibit STAT3/DNA binding with an IC50 of 0.61 mM and to exhibit promising cell growth inhibition in STAT3-dependent U266 multiple myeloma cells with an IC50 of 6.7 µM.

While the relative stereochemistry of phaeosphaeride A was deduced on the basis of NOE experiments, its absolute configuration remained undetermined (Maloney et al., 2006). Moreover, the attempts of total synthesis of phaeosphaeride A showed considerable differences in 1H and 13C NMR data between the synthetic and natural phaeosphaeride A (Kobayashi et al., 2011; Chatzimpaloglou et al., 2012, 2014). In 2015, Kobayashi and colleagues established the relative and absolute configurations of natural phaeosphaeride A by completing the first total synthesis of ent-phaeosphaeride A (Kobayashi et al., 2015).

Our research group isolated phaeosphaeride A from a fungal strain belonging to the genus Phoma. Phaeosphaeride A was obtained as an optically active (-108.33 (c 0.06, CH2Cl2)) yellow glass. 1H and 13C NMR data as well as mass spectra of our phaeosphaeride A match with the data reported for Clardy's natural phaeosphaeride A (Maloney et al., 2006). Optical rotation of Clardy's product (-93.6 (c 2.0, CH2Cl2)) and our phaeosphaeride A have the same sign. In this work we describe the crystal structure of natural phaeosphaeride A.

Experimental top

NMR spectra were recorded on a Bruker AVANCE III 400 MHz spectrometer in DMSO-d6. The same solvent was used as an inter­nal standard. High-resolution mass spectra (HRMS) were recorded on a LTQ Orbitrap Velos spectrometer. Optical rotations were determined on an Optical Activity AA-55 polarimeter using a 20 cm cell with a Na 589 nm filter.

Phaeosphaeride A was isolated from solid culture of the fungus Phoma sp. N 19. The microorganism was obtained from leaves of Cirsium arvense (L.) Scop. and deposited in the culture collection of the All-Russian Institute of Plant Protection (Saint-Petersburg, Russian Federation). The metabolite was purified from the fungal extract with a combination of preparative column chromatography and TLC on silica gel to give phaeosphaeride A as a yellow precipitate. (-108.33 (c 0.06, CH2Cl2); 1H NMR (400 MHz, DMSO-d6) δ 5.44 (d, J = 5.8 Hz, 1H), 4.97 (s, 2H), 4.92 (s, 1H), 4.07 (d, J = 11.3 Hz, 1H), 3.86 (d, J = 5.8 Hz, 1H), 3.79 (s, 3H), 1.82 (m, 1H), 1.58-1.22 (m, 7H), 1.19 (s, 3H), 0.86 (t, J = 6.4 Hz, 3H); 13C NMR (100.6 MHz, DMSO-d6) δ 166.53, 155.30, 137.12, 104.80, 90.80, 86.25, 70.96, 64.36, 63.76, 30.90, 27.60, 26.11, 21.96, 20.40, 13.85; HRMS [M + H]+ calcd for C15H24NO5 298.16490, found 298.16493. Recrystallization from heptane yielded yellow crystals (-116.66; -108.33 (c 0.06, CH2Cl2).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

H atoms bonded to C atoms were included in calculated positions and refined using a riding model, with Uiso(H) set to 1.2Ueq(C) and C–H = 0.97 Å for CH2 groups, Uiso(H) set to 1.5Ueq(N) and C–H = 0.96 Å for CH3 groups and Uiso(H) set to 1.2Ueq(N) and C–H = 0.93 Å for CH groups. All H atoms bonded to O atoms were located in a difference Fourier map and were refined with distance restraints and constrained displacement parameters OH 0.82 Å and Uiso(H) set to 1.2Ueq(O). The large thermal ellipsoid on C13 is characteristic for the distal end of long alkyl chains.

The structure of phaeosphaeride A (Fig.1) was refined as rotational twin [by a two-fold rotation about (001)] with twin fractions of 0.718 (6) and 0.282 (6). The 'HKLF 5' format file for the final refinement was generated by the TwinRotMat facility in Platon (Spek, 2009). The ratio (Fc2-Fo2)/esd for the reflections with the highest error in final refinement model (as a rotational twin) has lower residuals than in the initial solution. We have used Bayesian Statistics for verifying absolute structure. Supplementary crystallographic data for this paper have been deposited at Cambridge Crystallographic Data Centre (CCDC 1412515) and can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif.

Geometry top

The asymmetric unit contains two independent molecules of phaeosphaeride A (I and II) (fig. 1). Each molecule of phaeosphaeride A (numbering of atoms of phaeosphaeride A is given according to Clardy (Maloney et al., 2006)) contains two primary sections; an alkyl chain consisting of C(13)—C(12)—C(11)—C(10)—C(9) atoms and a cyclic system consisting of five and six membered rings with adjacent atoms.

For the five-membered ring C(1)—N(2)—C(3)—C(4)—C(5) of molecule I the Cremer-Pople (Cremer & Pople, 1975) parameters are Q=0.0714 Å, φ=197.99°, revealing a slightly distorted half-chair (2T1) conformation. Cremer-Pople parameters of Q=0.501 Å, θ=128.71°, φ=88.01° for the six-membered heterocycle of molecule I are consistent with a half-chair conformation (5H4). The geometric parameters of the six-membered rings for both molecules are similar, but the five-membered rings have different conformations. The five-membered ring in molecule II exhibits an envelope (1E) conformation.

Torsion angles O(1)—C(4)—C(5)—C(1) and C(3)—C(4)—C(5)—C(6) are -178.2 (4)° and -177.1 (4)° respectively, corresponding to co-planar conformation between the five and six-membered rings. The geometry of the heterocyclic ring system of the molecule (base of the half chair and the five-membered ring) is close to planar.

The exocyclic alkyl chain of I and the back of the half-chair lie approximately in the same plane. The deviation between the plane of alkyl atoms C(8)—C(9)—C(10)—C(11)—C(12)—C(13) and the back of the chair is 9.7 (4)°.

The geometric parameters are similar for both molecules I and II forming the weak hydrogen-bonded dimer through O2—H2···O2A. But angles characterizing the meth­oxy groups N(2)—O(5)—C(16) are slightly different (109.9 (3)° for I and 110.4 (4)° for II). The difference between angles O(4)—C(1)—C(5) is much greater with values of 129.4 (4)° and 123.2 (4)° for I and II respectively.

The molecules form layered structures. Nearly planar sheets, parallel with the (001) plane, form primary layers of two-dimensional hydrogen-bonded networks with the hydroxyl moieties located on the inter­ior of the sheets. The network (Fig. 2) is dependent primarily on four hydrogen bonds (Table 1) O2—H2···O2A, O3—H3···O4, O2A—H2A···O4, O3A—H3A···O4A (Desiraju et al., 1999; Arunan et al., 2011). In the (001) plane, two-dimensional hydrogen-bonded networks form a zig-zag pattern. The aliphatic butyl chains inter­digitate with the butyl chains on the adjacent sheets.

Related literature top

For details of the extraction of natural phaeosphaeride A and a discussion of its biological activities, see: Maloney et al. (2006). For details of trials of the synthesis of natural phaeosphaeride A, see: Kobayashi et al. (2011); Chatzimpaloglou et al. (2012, 2014); Kobayashi et al. (2015). Ring-puckering parameters are as defined by Cremer & Pople (1975). Hydrogen bonding is described in detail by Desiraju & Steiner (1999) and by Arunan et al. (2011). The twin law was identified using TwinRotMat in PLATON (Spek, 2009). Criteria for absolute configuration determination are described by Flack (1983) and Parsons et al. (2013).

Structure description top

In 2006, Clardy and colleagues isolated phaeosphaeride A from an endophytic fungus FA39 (Maloney et al., 2006). Phaeosphaeride A turned out to be an inhibitor of signal transduction and an activator of transcription 3 (STAT3)-dependent signaling. It was reported to selectively inhibit STAT3/DNA binding with an IC50 of 0.61 mM and to exhibit promising cell growth inhibition in STAT3-dependent U266 multiple myeloma cells with an IC50 of 6.7 µM.

While the relative stereochemistry of phaeosphaeride A was deduced on the basis of NOE experiments, its absolute configuration remained undetermined (Maloney et al., 2006). Moreover, the attempts of total synthesis of phaeosphaeride A showed considerable differences in 1H and 13C NMR data between the synthetic and natural phaeosphaeride A (Kobayashi et al., 2011; Chatzimpaloglou et al., 2012, 2014). In 2015, Kobayashi and colleagues established the relative and absolute configurations of natural phaeosphaeride A by completing the first total synthesis of ent-phaeosphaeride A (Kobayashi et al., 2015).

Our research group isolated phaeosphaeride A from a fungal strain belonging to the genus Phoma. Phaeosphaeride A was obtained as an optically active (-108.33 (c 0.06, CH2Cl2)) yellow glass. 1H and 13C NMR data as well as mass spectra of our phaeosphaeride A match with the data reported for Clardy's natural phaeosphaeride A (Maloney et al., 2006). Optical rotation of Clardy's product (-93.6 (c 2.0, CH2Cl2)) and our phaeosphaeride A have the same sign. In this work we describe the crystal structure of natural phaeosphaeride A.

NMR spectra were recorded on a Bruker AVANCE III 400 MHz spectrometer in DMSO-d6. The same solvent was used as an inter­nal standard. High-resolution mass spectra (HRMS) were recorded on a LTQ Orbitrap Velos spectrometer. Optical rotations were determined on an Optical Activity AA-55 polarimeter using a 20 cm cell with a Na 589 nm filter.

Phaeosphaeride A was isolated from solid culture of the fungus Phoma sp. N 19. The microorganism was obtained from leaves of Cirsium arvense (L.) Scop. and deposited in the culture collection of the All-Russian Institute of Plant Protection (Saint-Petersburg, Russian Federation). The metabolite was purified from the fungal extract with a combination of preparative column chromatography and TLC on silica gel to give phaeosphaeride A as a yellow precipitate. (-108.33 (c 0.06, CH2Cl2); 1H NMR (400 MHz, DMSO-d6) δ 5.44 (d, J = 5.8 Hz, 1H), 4.97 (s, 2H), 4.92 (s, 1H), 4.07 (d, J = 11.3 Hz, 1H), 3.86 (d, J = 5.8 Hz, 1H), 3.79 (s, 3H), 1.82 (m, 1H), 1.58-1.22 (m, 7H), 1.19 (s, 3H), 0.86 (t, J = 6.4 Hz, 3H); 13C NMR (100.6 MHz, DMSO-d6) δ 166.53, 155.30, 137.12, 104.80, 90.80, 86.25, 70.96, 64.36, 63.76, 30.90, 27.60, 26.11, 21.96, 20.40, 13.85; HRMS [M + H]+ calcd for C15H24NO5 298.16490, found 298.16493. Recrystallization from heptane yielded yellow crystals (-116.66; -108.33 (c 0.06, CH2Cl2).

The asymmetric unit contains two independent molecules of phaeosphaeride A (I and II) (fig. 1). Each molecule of phaeosphaeride A (numbering of atoms of phaeosphaeride A is given according to Clardy (Maloney et al., 2006)) contains two primary sections; an alkyl chain consisting of C(13)—C(12)—C(11)—C(10)—C(9) atoms and a cyclic system consisting of five and six membered rings with adjacent atoms.

For the five-membered ring C(1)—N(2)—C(3)—C(4)—C(5) of molecule I the Cremer-Pople (Cremer & Pople, 1975) parameters are Q=0.0714 Å, φ=197.99°, revealing a slightly distorted half-chair (2T1) conformation. Cremer-Pople parameters of Q=0.501 Å, θ=128.71°, φ=88.01° for the six-membered heterocycle of molecule I are consistent with a half-chair conformation (5H4). The geometric parameters of the six-membered rings for both molecules are similar, but the five-membered rings have different conformations. The five-membered ring in molecule II exhibits an envelope (1E) conformation.

Torsion angles O(1)—C(4)—C(5)—C(1) and C(3)—C(4)—C(5)—C(6) are -178.2 (4)° and -177.1 (4)° respectively, corresponding to co-planar conformation between the five and six-membered rings. The geometry of the heterocyclic ring system of the molecule (base of the half chair and the five-membered ring) is close to planar.

The exocyclic alkyl chain of I and the back of the half-chair lie approximately in the same plane. The deviation between the plane of alkyl atoms C(8)—C(9)—C(10)—C(11)—C(12)—C(13) and the back of the chair is 9.7 (4)°.

The geometric parameters are similar for both molecules I and II forming the weak hydrogen-bonded dimer through O2—H2···O2A. But angles characterizing the meth­oxy groups N(2)—O(5)—C(16) are slightly different (109.9 (3)° for I and 110.4 (4)° for II). The difference between angles O(4)—C(1)—C(5) is much greater with values of 129.4 (4)° and 123.2 (4)° for I and II respectively.

The molecules form layered structures. Nearly planar sheets, parallel with the (001) plane, form primary layers of two-dimensional hydrogen-bonded networks with the hydroxyl moieties located on the inter­ior of the sheets. The network (Fig. 2) is dependent primarily on four hydrogen bonds (Table 1) O2—H2···O2A, O3—H3···O4, O2A—H2A···O4, O3A—H3A···O4A (Desiraju et al., 1999; Arunan et al., 2011). In the (001) plane, two-dimensional hydrogen-bonded networks form a zig-zag pattern. The aliphatic butyl chains inter­digitate with the butyl chains on the adjacent sheets.

For details of the extraction of natural phaeosphaeride A and a discussion of its biological activities, see: Maloney et al. (2006). For details of trials of the synthesis of natural phaeosphaeride A, see: Kobayashi et al. (2011); Chatzimpaloglou et al. (2012, 2014); Kobayashi et al. (2015). Ring-puckering parameters are as defined by Cremer & Pople (1975). Hydrogen bonding is described in detail by Desiraju & Steiner (1999) and by Arunan et al. (2011). The twin law was identified using TwinRotMat in PLATON (Spek, 2009). Criteria for absolute configuration determination are described by Flack (1983) and Parsons et al. (2013).

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 1.

H atoms bonded to C atoms were included in calculated positions and refined using a riding model, with Uiso(H) set to 1.2Ueq(C) and C–H = 0.97 Å for CH2 groups, Uiso(H) set to 1.5Ueq(N) and C–H = 0.96 Å for CH3 groups and Uiso(H) set to 1.2Ueq(N) and C–H = 0.93 Å for CH groups. All H atoms bonded to O atoms were located in a difference Fourier map and were refined with distance restraints and constrained displacement parameters OH 0.82 Å and Uiso(H) set to 1.2Ueq(O). The large thermal ellipsoid on C13 is characteristic for the distal end of long alkyl chains.

The structure of phaeosphaeride A (Fig.1) was refined as rotational twin [by a two-fold rotation about (001)] with twin fractions of 0.718 (6) and 0.282 (6). The 'HKLF 5' format file for the final refinement was generated by the TwinRotMat facility in Platon (Spek, 2009). The ratio (Fc2-Fo2)/esd for the reflections with the highest error in final refinement model (as a rotational twin) has lower residuals than in the initial solution. We have used Bayesian Statistics for verifying absolute structure. Supplementary crystallographic data for this paper have been deposited at Cambridge Crystallographic Data Centre (CCDC 1412515) and can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. A view of molecules I (left) and II (right) of phaeosphaeride A. The atom numbering scheme is that of Maloney et al. (2006). Displacement ellipsoids are shown at the 50% probability level.
[Figure 2] Fig. 2. Projection of the layered crystal structure of phaeosphaeride A on the (100) plane. The dashed lines indicate the short contacts between molecules of phaeosphaeride A (only hydrogen atoms forming hydrogen bonds are shown).
3,4-Dihydroxy-6-methoxy-3-methyl-7-methylidene-2-pentyl-3,4-dihydro-2H,7H-pyrano[2,3-c]pyrrol-5(6H)-one top
Crystal data top
C15H23NO5F(000) = 640
Mr = 297.34Dx = 1.235 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
a = 10.14078 (18) ÅCell parameters from 14376 reflections
b = 9.10361 (14) Åθ = 4.4–75.9°
c = 17.5991 (3) ŵ = 0.77 mm1
β = 100.1847 (16)°T = 100 K
V = 1599.11 (5) Å3Tabular, colourless
Z = 40.35 × 0.35 × 0.05 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Atlas detector
6054 measured reflections
Radiation source: SuperNova (Cu) X-ray Source6054 independent reflections
Mirror monochromator5940 reflections with I > 2σ(I)
Detector resolution: 10.3829 pixels mm-1θmax = 70.0°, θmin = 4.4°
ω scansh = 1212
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 1111
Tmin = 0.824, Tmax = 1.000l = 421
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.058 w = 1/[σ2(Fo2) + (0.0289P)2 + 2.9758P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.150(Δ/σ)max < 0.001
S = 1.10Δρmax = 0.36 e Å3
6054 reflectionsΔρmin = 0.30 e Å3
389 parametersAbsolute structure: Flack x determined using 2632 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.05 (8)
Crystal data top
C15H23NO5V = 1599.11 (5) Å3
Mr = 297.34Z = 4
Monoclinic, P21Cu Kα radiation
a = 10.14078 (18) ŵ = 0.77 mm1
b = 9.10361 (14) ÅT = 100 K
c = 17.5991 (3) Å0.35 × 0.35 × 0.05 mm
β = 100.1847 (16)°
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Atlas detector
6054 measured reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
6054 independent reflections
Tmin = 0.824, Tmax = 1.0005940 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.150Δρmax = 0.36 e Å3
S = 1.10Δρmin = 0.30 e Å3
6054 reflectionsAbsolute structure: Flack x determined using 2632 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
389 parametersAbsolute structure parameter: 0.05 (8)
1 restraint
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C11.1431 (5)0.8972 (6)0.9253 (3)0.0153 (10)
N21.1842 (4)0.7850 (5)0.8817 (2)0.0163 (9)
C31.1862 (5)0.8314 (6)0.8053 (3)0.0149 (10)
C41.1266 (5)0.9782 (6)0.8025 (3)0.0143 (10)
C51.0975 (5)1.0166 (5)0.8717 (3)0.0135 (9)
C61.0311 (5)1.1589 (6)0.8845 (3)0.0159 (10)
H61.09841.22690.91150.019*
C70.9703 (5)1.2250 (6)0.8039 (3)0.0167 (10)
C81.0752 (5)1.2122 (5)0.7508 (3)0.0144 (10)
H81.15801.25960.77650.017*
C91.0343 (5)1.2809 (6)0.6718 (3)0.0194 (11)
H9A1.00061.37910.67790.023*
H9B0.96201.22370.64260.023*
C101.1482 (5)1.2899 (7)0.6264 (3)0.0231 (11)
H10A1.18551.19240.62310.028*
H10B1.21831.35190.65430.028*
C111.1059 (7)1.3504 (8)0.5454 (4)0.0349 (15)
H11A1.03801.28640.51710.042*
H11B1.06571.44630.54870.042*
C121.2195 (8)1.3646 (9)0.5007 (4)0.0433 (19)
H12A1.26271.26970.49980.052*
H12B1.28521.43260.52780.052*
C131.1771 (12)1.4175 (13)0.4187 (5)0.080 (4)
H13A1.11191.35110.39130.120*
H13B1.25381.42110.39360.120*
H13C1.13871.51380.41890.120*
C141.2311 (5)0.7567 (6)0.7508 (3)0.0213 (11)
H14A1.26600.66290.76110.026*
H14B1.22770.79790.70210.026*
C150.8381 (5)1.1508 (6)0.7705 (3)0.0193 (10)
H15A0.85401.04950.76000.029*
H15B0.79861.19920.72350.029*
H15C0.77821.15700.80700.029*
C161.2068 (6)0.5407 (6)0.9208 (3)0.0203 (11)
H16A1.16480.51030.87010.031*
H16B1.14000.55210.95280.031*
H16C1.27060.46780.94290.031*
O11.1050 (4)1.0568 (4)0.73717 (19)0.0172 (7)
O20.9541 (4)1.3789 (4)0.8112 (2)0.0183 (8)
H20.89421.39510.83590.027*
O30.9324 (4)1.1327 (4)0.9312 (2)0.0213 (8)
H30.90601.21140.94560.032*
O41.1447 (4)0.8881 (4)0.99543 (19)0.0183 (8)
O51.2747 (4)0.6794 (4)0.9159 (2)0.0194 (8)
C1A0.4815 (5)1.9716 (6)0.8996 (3)0.0156 (10)
N2A0.4361 (4)2.0638 (5)0.8379 (2)0.0174 (9)
C3A0.4890 (5)2.0271 (6)0.7717 (3)0.0159 (10)
C4A0.5564 (5)1.8865 (6)0.7938 (3)0.0136 (9)
C5A0.5529 (5)1.8520 (5)0.8678 (3)0.0147 (10)
C6A0.6116 (5)1.7116 (5)0.9032 (3)0.0140 (10)
H6A0.53931.63980.90200.017*
C7A0.7097 (5)1.6545 (5)0.8525 (3)0.0126 (9)
C8A0.6355 (5)1.6563 (5)0.7676 (3)0.0140 (10)
H8A0.54981.60550.76560.017*
C9A0.7086 (5)1.5840 (6)0.7096 (3)0.0191 (11)
H9AA0.74191.48910.72960.023*
H9AB0.78531.64390.70380.023*
C10A0.6212 (6)1.5621 (7)0.6302 (3)0.0223 (11)
H10C0.53841.51390.63640.027*
H10D0.59861.65720.60660.027*
C11A0.6921 (6)1.4697 (7)0.5771 (3)0.0270 (13)
H11C0.77321.52020.56990.032*
H11D0.71831.37680.60230.032*
C12A0.6074 (6)1.4392 (8)0.4983 (3)0.0295 (14)
H12C0.58051.53180.47300.035*
H12D0.52691.38710.50510.035*
C13A0.6823 (7)1.3483 (8)0.4466 (3)0.0344 (15)
H13D0.62441.32970.39820.052*
H13E0.70961.25660.47150.052*
H13F0.75991.40130.43770.052*
C14A0.4806 (5)2.1038 (6)0.7075 (3)0.0210 (11)
H14C0.43562.19320.70260.025*
H14D0.51982.06850.66710.025*
C15A0.8399 (5)1.7422 (6)0.8646 (3)0.0160 (10)
H15D0.82011.84440.85500.024*
H15E0.89581.70770.82960.024*
H15F0.88581.72980.91680.024*
C16A0.5035 (6)2.3002 (6)0.8752 (4)0.0273 (12)
H16D0.56162.29980.83760.041*
H16E0.55202.26630.92380.041*
H16F0.47192.39830.88090.041*
O1A0.6069 (4)1.8064 (4)0.74144 (18)0.0166 (7)
O2A0.7369 (3)1.5024 (4)0.86892 (19)0.0145 (7)
H2A0.74101.48770.91520.022*
O3A0.6775 (3)1.7297 (4)0.98091 (18)0.0145 (7)
H3A0.63631.68501.00970.022*
O4A0.4586 (4)1.9909 (4)0.9650 (2)0.0179 (7)
O5A0.3911 (4)2.2045 (4)0.8499 (2)0.0186 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.015 (2)0.013 (2)0.017 (2)0.004 (2)0.0009 (19)0.0023 (19)
N20.016 (2)0.013 (2)0.018 (2)0.0036 (17)0.0009 (16)0.0025 (17)
C30.011 (2)0.018 (2)0.016 (2)0.0028 (19)0.0039 (18)0.0019 (19)
C40.014 (2)0.016 (2)0.015 (2)0.0008 (19)0.0064 (18)0.0002 (19)
C50.010 (2)0.014 (2)0.017 (2)0.0018 (19)0.0024 (17)0.0027 (19)
C60.017 (2)0.017 (2)0.014 (2)0.001 (2)0.0063 (19)0.0035 (19)
C70.017 (2)0.012 (2)0.022 (3)0.001 (2)0.006 (2)0.0002 (19)
C80.013 (2)0.012 (2)0.017 (2)0.0003 (18)0.0002 (18)0.0007 (19)
C90.018 (2)0.021 (3)0.018 (2)0.005 (2)0.0005 (19)0.006 (2)
C100.022 (3)0.027 (3)0.020 (3)0.009 (2)0.003 (2)0.008 (2)
C110.037 (4)0.041 (4)0.027 (3)0.016 (3)0.009 (3)0.017 (3)
C120.055 (5)0.047 (4)0.035 (3)0.015 (4)0.027 (3)0.021 (3)
C130.113 (9)0.095 (8)0.046 (5)0.054 (7)0.049 (5)0.046 (5)
C140.021 (3)0.022 (3)0.022 (3)0.005 (2)0.009 (2)0.002 (2)
C150.016 (2)0.020 (3)0.021 (2)0.000 (2)0.003 (2)0.000 (2)
C160.024 (3)0.012 (2)0.026 (3)0.000 (2)0.007 (2)0.000 (2)
O10.0200 (18)0.0170 (18)0.0144 (16)0.0042 (15)0.0022 (13)0.0008 (14)
O20.0174 (18)0.0135 (17)0.0253 (19)0.0032 (14)0.0075 (15)0.0004 (14)
O30.030 (2)0.0158 (18)0.0222 (18)0.0035 (16)0.0158 (16)0.0017 (15)
O40.0252 (19)0.0170 (17)0.0123 (16)0.0038 (15)0.0022 (14)0.0014 (14)
O50.0177 (18)0.0127 (18)0.0263 (19)0.0023 (14)0.0006 (15)0.0034 (14)
C1A0.013 (2)0.013 (2)0.021 (2)0.0010 (19)0.0022 (19)0.0025 (19)
N2A0.021 (2)0.011 (2)0.020 (2)0.0053 (18)0.0049 (17)0.0022 (17)
C3A0.010 (2)0.016 (2)0.023 (2)0.0024 (19)0.0038 (18)0.005 (2)
C4A0.010 (2)0.014 (2)0.017 (2)0.0044 (19)0.0032 (18)0.0027 (19)
C5A0.013 (2)0.014 (2)0.019 (2)0.0059 (19)0.0059 (19)0.0034 (19)
C6A0.016 (2)0.014 (2)0.012 (2)0.0061 (19)0.0038 (18)0.0016 (18)
C7A0.012 (2)0.011 (2)0.015 (2)0.0008 (19)0.0008 (18)0.0019 (18)
C8A0.014 (2)0.014 (2)0.013 (2)0.0007 (19)0.0007 (18)0.0015 (18)
C9A0.018 (3)0.024 (3)0.015 (2)0.006 (2)0.002 (2)0.000 (2)
C10A0.023 (3)0.028 (3)0.016 (2)0.006 (2)0.004 (2)0.005 (2)
C11A0.031 (3)0.032 (3)0.018 (3)0.010 (3)0.003 (2)0.004 (2)
C12A0.029 (3)0.041 (4)0.019 (3)0.006 (3)0.003 (2)0.008 (2)
C13A0.040 (4)0.043 (4)0.020 (3)0.003 (3)0.005 (3)0.010 (3)
C14A0.021 (3)0.021 (3)0.021 (3)0.005 (2)0.005 (2)0.003 (2)
C15A0.017 (2)0.018 (2)0.014 (2)0.002 (2)0.0056 (18)0.0015 (19)
C16A0.029 (3)0.017 (3)0.036 (3)0.011 (2)0.006 (2)0.008 (2)
O1A0.0188 (17)0.0195 (18)0.0120 (15)0.0060 (15)0.0039 (13)0.0011 (14)
O2A0.0181 (17)0.0128 (17)0.0122 (15)0.0024 (14)0.0016 (13)0.0016 (13)
O3A0.0175 (17)0.0154 (17)0.0104 (15)0.0013 (14)0.0022 (13)0.0008 (13)
O4A0.0234 (19)0.0152 (18)0.0175 (17)0.0020 (15)0.0105 (14)0.0016 (14)
O5A0.0157 (18)0.0102 (17)0.0301 (19)0.0022 (14)0.0044 (15)0.0040 (15)
Geometric parameters (Å, º) top
C1—N21.385 (7)C1A—N2A1.386 (7)
C1—C51.460 (7)C1A—C5A1.472 (7)
C1—O41.234 (6)C1A—O4A1.226 (6)
N2—C31.412 (6)N2A—C3A1.406 (7)
N2—O51.391 (5)N2A—O5A1.389 (5)
C3—C41.463 (7)C3A—C4A1.471 (7)
C3—C141.320 (7)C3A—C14A1.318 (7)
C4—C51.349 (7)C4A—C5A1.347 (7)
C4—O11.339 (6)C4A—O1A1.345 (6)
C5—C61.495 (7)C5A—C6A1.498 (7)
C6—H60.9800C6A—H6A0.9800
C6—C71.563 (7)C6A—C7A1.540 (7)
C6—O31.423 (6)C6A—O3A1.422 (6)
C7—C81.540 (7)C7A—C8A1.549 (6)
C7—C151.523 (7)C7A—C15A1.526 (7)
C7—O21.419 (6)C7A—O2A1.431 (6)
C8—H80.9800C8A—H8A0.9800
C8—C91.514 (7)C8A—C9A1.515 (7)
C8—O11.475 (6)C8A—O1A1.455 (6)
C9—H9A0.9700C9A—H9AA0.9700
C9—H9B0.9700C9A—H9AB0.9700
C9—C101.518 (7)C9A—C10A1.529 (7)
C10—H10A0.9700C10A—H10C0.9700
C10—H10B0.9700C10A—H10D0.9700
C10—C111.519 (7)C10A—C11A1.528 (7)
C11—H11A0.9700C11A—H11C0.9700
C11—H11B0.9700C11A—H11D0.9700
C11—C121.510 (9)C11A—C12A1.523 (8)
C12—H12A0.9700C12A—H12C0.9700
C12—H12B0.9700C12A—H12D0.9700
C12—C131.511 (10)C12A—C13A1.527 (8)
C13—H13A0.9600C13A—H13D0.9600
C13—H13B0.9600C13A—H13E0.9600
C13—H13C0.9600C13A—H13F0.9600
C14—H14A0.9300C14A—H14C0.9300
C14—H14B0.9300C14A—H14D0.9300
C15—H15A0.9600C15A—H15D0.9600
C15—H15B0.9600C15A—H15E0.9600
C15—H15C0.9600C15A—H15F0.9600
C16—H16A0.9600C16A—H16D0.9600
C16—H16B0.9600C16A—H16E0.9600
C16—H16C0.9600C16A—H16F0.9600
C16—O51.448 (6)C16A—O5A1.442 (6)
O2—H20.8200O2A—H2A0.8200
O3—H30.8200O3A—H3A0.8200
N2—C1—C5106.4 (4)N2A—C1A—C5A105.5 (4)
O4—C1—N2123.6 (5)O4A—C1A—N2A123.9 (5)
O4—C1—C5129.9 (5)O4A—C1A—C5A130.6 (5)
C1—N2—C3111.3 (4)C1A—N2A—C3A112.5 (4)
C1—N2—O5120.6 (4)C1A—N2A—O5A120.8 (4)
O5—N2—C3120.0 (4)O5A—N2A—C3A122.0 (4)
N2—C3—C4103.3 (4)N2A—C3A—C4A102.4 (4)
C14—C3—N2127.0 (5)C14A—C3A—N2A127.4 (5)
C14—C3—C4129.7 (5)C14A—C3A—C4A130.1 (5)
C5—C4—C3111.2 (4)C5A—C4A—C3A111.6 (4)
O1—C4—C3121.4 (4)O1A—C4A—C3A120.4 (4)
O1—C4—C5127.4 (5)O1A—C4A—C5A127.9 (5)
C1—C5—C6130.4 (4)C1A—C5A—C6A131.2 (4)
C4—C5—C1107.1 (4)C4A—C5A—C1A107.1 (4)
C4—C5—C6122.5 (5)C4A—C5A—C6A121.6 (4)
C5—C6—H6109.0C5A—C6A—H6A108.7
C5—C6—C7108.3 (4)C5A—C6A—C7A107.3 (4)
C7—C6—H6109.0C7A—C6A—H6A108.7
O3—C6—C5108.9 (4)O3A—C6A—C5A112.7 (4)
O3—C6—H6109.0O3A—C6A—H6A108.7
O3—C6—C7112.6 (4)O3A—C6A—C7A110.8 (4)
C8—C7—C6108.5 (4)C6A—C7A—C8A107.6 (4)
C15—C7—C6111.0 (4)C15A—C7A—C6A112.0 (4)
C15—C7—C8112.8 (4)C15A—C7A—C8A113.0 (4)
O2—C7—C6109.4 (4)O2A—C7A—C6A109.3 (4)
O2—C7—C8103.5 (4)O2A—C7A—C8A104.4 (4)
O2—C7—C15111.4 (4)O2A—C7A—C15A110.3 (4)
C7—C8—H8108.3C7A—C8A—H8A107.8
C9—C8—C7114.8 (4)C9A—C8A—C7A115.7 (4)
C9—C8—H8108.3C9A—C8A—H8A107.8
O1—C8—C7110.8 (4)O1A—C8A—C7A110.5 (4)
O1—C8—H8108.3O1A—C8A—H8A107.8
O1—C8—C9106.1 (4)O1A—C8A—C9A106.8 (4)
C8—C9—H9A108.9C8A—C9A—H9AA108.9
C8—C9—H9B108.9C8A—C9A—H9AB108.9
C8—C9—C10113.3 (4)C8A—C9A—C10A113.5 (4)
H9A—C9—H9B107.7H9AA—C9A—H9AB107.7
C10—C9—H9A108.9C10A—C9A—H9AA108.9
C10—C9—H9B108.9C10A—C9A—H9AB108.9
C9—C10—H10A108.9C9A—C10A—H10C109.3
C9—C10—H10B108.9C9A—C10A—H10D109.3
C9—C10—C11113.5 (4)H10C—C10A—H10D107.9
H10A—C10—H10B107.7C11A—C10A—C9A111.7 (5)
C11—C10—H10A108.9C11A—C10A—H10C109.3
C11—C10—H10B108.9C11A—C10A—H10D109.3
C10—C11—H11A108.8C10A—C11A—H11C108.7
C10—C11—H11B108.8C10A—C11A—H11D108.7
H11A—C11—H11B107.7H11C—C11A—H11D107.6
C12—C11—C10113.9 (5)C12A—C11A—C10A114.0 (5)
C12—C11—H11A108.8C12A—C11A—H11C108.7
C12—C11—H11B108.8C12A—C11A—H11D108.7
C11—C12—H12A108.7C11A—C12A—H12C109.1
C11—C12—H12B108.7C11A—C12A—H12D109.1
C11—C12—C13114.2 (7)C11A—C12A—C13A112.4 (5)
H12A—C12—H12B107.6H12C—C12A—H12D107.8
C13—C12—H12A108.7C13A—C12A—H12C109.1
C13—C12—H12B108.7C13A—C12A—H12D109.1
C12—C13—H13A109.5C12A—C13A—H13D109.5
C12—C13—H13B109.5C12A—C13A—H13E109.5
C12—C13—H13C109.5C12A—C13A—H13F109.5
H13A—C13—H13B109.5H13D—C13A—H13E109.5
H13A—C13—H13C109.5H13D—C13A—H13F109.5
H13B—C13—H13C109.5H13E—C13A—H13F109.5
C3—C14—H14A120.0C3A—C14A—H14C120.0
C3—C14—H14B120.0C3A—C14A—H14D120.0
H14A—C14—H14B120.0H14C—C14A—H14D120.0
C7—C15—H15A109.5C7A—C15A—H15D109.5
C7—C15—H15B109.5C7A—C15A—H15E109.5
C7—C15—H15C109.5C7A—C15A—H15F109.5
H15A—C15—H15B109.5H15D—C15A—H15E109.5
H15A—C15—H15C109.5H15D—C15A—H15F109.5
H15B—C15—H15C109.5H15E—C15A—H15F109.5
H16A—C16—H16B109.5H16D—C16A—H16E109.5
H16A—C16—H16C109.5H16D—C16A—H16F109.5
H16B—C16—H16C109.5H16E—C16A—H16F109.5
O5—C16—H16A109.5O5A—C16A—H16D109.5
O5—C16—H16B109.5O5A—C16A—H16E109.5
O5—C16—H16C109.5O5A—C16A—H16F109.5
C4—O1—C8112.3 (4)C4A—O1A—C8A111.8 (4)
C7—O2—H2109.5C7A—O2A—H2A109.5
C6—O3—H3109.5C6A—O3A—H3A109.5
N2—O5—C16110.1 (4)N2A—O5A—C16A109.9 (4)
C1—N2—C3—C46.7 (5)C1A—N2A—C3A—C4A8.7 (5)
C1—N2—C3—C14173.8 (5)C1A—N2A—C3A—C14A170.0 (5)
C1—N2—O5—C16107.4 (5)C1A—N2A—O5A—C16A76.8 (6)
C1—C5—C6—C7165.0 (5)C1A—C5A—C6A—C7A162.9 (5)
C1—C5—C6—O342.4 (7)C1A—C5A—C6A—O3A40.7 (7)
N2—C1—C5—C46.6 (5)N2A—C1A—C5A—C4A5.5 (5)
N2—C1—C5—C6173.7 (5)N2A—C1A—C5A—C6A172.8 (5)
N2—C3—C4—C52.4 (5)N2A—C3A—C4A—C5A5.0 (5)
N2—C3—C4—O1176.8 (4)N2A—C3A—C4A—O1A172.2 (4)
C3—N2—O5—C16106.7 (5)C3A—N2A—O5A—C16A77.1 (6)
C3—C4—C5—C12.5 (6)C3A—C4A—C5A—C1A0.2 (6)
C3—C4—C5—C6177.7 (4)C3A—C4A—C5A—C6A178.2 (4)
C3—C4—O1—C8166.3 (4)C3A—C4A—O1A—C8A164.3 (4)
C4—C5—C6—C715.3 (7)C4A—C5A—C6A—C7A19.1 (6)
C4—C5—C6—O3137.9 (5)C4A—C5A—C6A—O3A141.3 (4)
C5—C1—N2—C38.4 (6)C5A—C1A—N2A—C3A9.1 (6)
C5—C1—N2—O5157.1 (4)C5A—C1A—N2A—O5A165.3 (4)
C5—C4—O1—C814.7 (7)C5A—C4A—O1A—C8A12.4 (7)
C5—C6—C7—C845.3 (5)C5A—C6A—C7A—C8A49.7 (5)
C5—C6—C7—C1579.3 (5)C5A—C6A—C7A—C15A75.0 (5)
C5—C6—C7—O2157.4 (4)C5A—C6A—C7A—O2A162.5 (4)
C6—C7—C8—C9176.2 (4)C6A—C7A—C8A—C9A171.8 (4)
C6—C7—C8—O163.7 (5)C6A—C7A—C8A—O1A66.7 (5)
C7—C8—C9—C10170.0 (5)C7A—C8A—C9A—C10A168.8 (4)
C7—C8—O1—C447.0 (5)C7A—C8A—O1A—C4A45.8 (5)
C8—C9—C10—C11176.6 (5)C8A—C9A—C10A—C11A171.9 (5)
C9—C8—O1—C4172.2 (4)C9A—C8A—O1A—C4A172.5 (4)
C9—C10—C11—C12178.0 (6)C9A—C10A—C11A—C12A177.7 (5)
C10—C11—C12—C13177.0 (8)C10A—C11A—C12A—C13A179.3 (6)
C14—C3—C4—C5178.1 (5)C14A—C3A—C4A—C5A173.7 (5)
C14—C3—C4—O12.7 (8)C14A—C3A—C4A—O1A9.1 (8)
C15—C7—C8—C960.4 (6)C15A—C7A—C8A—C9A64.2 (6)
C15—C7—C8—O159.7 (5)C15A—C7A—C8A—O1A57.4 (5)
O1—C4—C5—C1178.4 (5)O1A—C4A—C5A—C1A177.1 (5)
O1—C4—C5—C61.4 (8)O1A—C4A—C5A—C6A1.3 (8)
O1—C8—C9—C1067.3 (6)O1A—C8A—C9A—C10A67.7 (6)
O2—C7—C8—C960.1 (5)O2A—C7A—C8A—C9A55.7 (5)
O2—C7—C8—O1179.8 (4)O2A—C7A—C8A—O1A177.2 (4)
O3—C6—C7—C8165.6 (4)O3A—C6A—C7A—C8A173.1 (4)
O3—C6—C7—C1541.1 (6)O3A—C6A—C7A—C15A48.4 (5)
O3—C6—C7—O282.2 (5)O3A—C6A—C7A—O2A74.1 (5)
O4—C1—N2—C3173.2 (5)O4A—C1A—N2A—C3A173.0 (5)
O4—C1—N2—O524.5 (7)O4A—C1A—N2A—O5A16.8 (8)
O4—C1—C5—C4175.2 (5)O4A—C1A—C5A—C4A176.8 (5)
O4—C1—C5—C64.6 (9)O4A—C1A—C5A—C6A5.0 (9)
O5—N2—C3—C4155.6 (4)O5A—N2A—C3A—C4A164.6 (4)
O5—N2—C3—C1424.9 (8)O5A—N2A—C3A—C14A14.2 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O2A0.822.042.818 (5)158
O3—H3···O4i0.822.032.836 (5)168
O2A—H2A···O4i0.822.002.685 (5)141
O3A—H3A···O4Aii0.822.102.829 (5)149
Symmetry codes: (i) x+2, y+1/2, z+2; (ii) x+1, y1/2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O2A0.822.042.818 (5)157.8
O3—H3···O4i0.822.032.836 (5)167.5
O2A—H2A···O4i0.822.002.685 (5)141.0
O3A—H3A···O4Aii0.822.102.829 (5)148.5
Symmetry codes: (i) x+2, y+1/2, z+2; (ii) x+1, y1/2, z+2.
 

Acknowledgements

XRD study was completed at the X-ray Diffraction Centre of St Petersburg State University. The research was financially supported by Russian Scientific Fund (project No. 14-26-00067).

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