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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 8| August 2015| Pages o558-o559
https://doi.org/10.1107/S2056989015012670

Crystal structure of 3-hy­dr­oxy­methyl-1,2,3,4-tetra­hydro­isoquinolin-1-one

Ignez Caracelli,a* Camila Lury Hino,b Julio Zukerman-Schpector,b Francisco Carlos Biaggioc and Edward R. T. Tiekinkd

aDepartmento de Física, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, bDepartmento de Química, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, cEscola de Engenharia de Lorena - EEL, Universidade São Paulo, SP, Brazil, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: ignez@ufscar.br

Edited by P. C. Healy, Griffith University, Australia (Received 29 June 2015; accepted 1 July 2015; online 8 July 2015)

In the title compound, C10H11NO2, two independent but virtually superimposable mol­ecules, A and B, comprise the asymmetric unit. The heterocyclic ring in each mol­ecule has a screw-boat conformation, and the methyl­hydroxyl group occupies a position to one side of this ring with N—C—C—O torsion angles of −55.30 (15) (mol­ecule A) and −55.94 (16)° (mol­ecule B). In the crystal, O—H⋯O and N—H⋯O hydrogen bonding leads to 11-membered {⋯HNCO⋯HO⋯HNC2O} heterosynthons, involving three different mol­ecules, which are edge-shared to generate a supra­molecular chain along the a axis. Inter­actions of the type C—H⋯O provide additional stability to the chains, and link these into a three-dimensional architecture.

CCDC reference: 1409827

Similar articles

1. Related literature

For background, including medicinal potential, to compounds related to the title compound, see: Biaggio et al. (2007[Biaggio, F. C., Rufino, A. R. & Silveira, M. C. F. (2007). Lett. Org. Chem. 4, 1-3.]); Grunewald et al. (1999[Grunewald, G. L., Caldwell, T. M., Li, Q., Dahanukar, V. H., McNeil, B. & Criscione, K. R. (1999). J. Med. Chem. 42, 4351-4361.]); Zoretic & Soja (1977[Zoretic, P. A. & Soja, P. (1977). J. Heterocycl. Chem. 14, 1267-1269.]). For additional conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C10H11NO2

  • Mr = 177.20

  • Orthorhombic, P 21 21 21

  • a = 6.2846 (1) Å

  • b = 13.8914 (1) Å

  • c = 19.5592 (2) Å

  • V = 1707.56 (3) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 0.79 mm−1

  • T = 100 K

  • 0.35 × 0.25 × 0.15 mm

2.2. Data collection

  • Agilent SuperNova CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.882, Tmax = 1.000

  • 6258 measured reflections

  • 3358 independent reflections

  • 3336 reflections with I > 2σ(I)

  • Rint = 0.011

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.070

  • S = 1.06

  • 3358 reflections

  • 251 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.29 e Å−3

  • Absolute structure: Flack x determined using 1359 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 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2O⋯O1i 0.85 (1) 1.86 (1) 2.7066 (14) 176 (3)
O4—H4O⋯O3i 0.86 (1) 1.83 (1) 2.6808 (15) 178 (3)
N1—H1N⋯O4 0.86 (1) 2.05 (1) 2.9141 (15) 176 (2)
N2—H2N⋯O2ii 0.87 (1) 2.00 (1) 2.8737 (15) 179 (2)
C4—H4⋯O2iii 0.95 2.53 3.2512 (18) 132
C8—H8A⋯O1i 0.99 2.48 3.3157 (16) 142
C18—H18A⋯O3i 0.99 2.55 3.4007 (16) 145
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z; (iii) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2014 (Burla et al., 2015[Burla, M. C., Caliandro, R., Carrozzini, B., Cascarano, G. L., Cuocci, C., Giacovazzo, C., Mallamo, M., Mazzone, A. & Polidori, G. (2015). J. Appl. Cryst. 48, 306-309.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), QMOL (Gans & Shalloway, 2001[Gans, J. & Shalloway, D. (2001). J. Mol. Graphics Model. 19, 557-559.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010[ChemAxon (2010). Marvinsketch. http://www.chemaxon.com.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 1409827

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015012670/hg5449sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015012670/hg5449Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015012670/hg5449Isup3.cml

checkCIF report


Structural commentary top

Referring to Fig. 1, the treatment of la­ctam carbonate (1) with sodium hydride to form compound (2) was unsuccessful and led only to the la­ctam alcohol product (3). Compound (3) might be used as an inter­mediate in organic synthesis. The heterocyclic ring has a screw-boat conformation with puckering parameters (Cremer & Pople, 1975): Puckering Amplitude (Q) = 0.4213 (14) Å, θ = 64.15 (19)° and φ = 271.6 (2)° (molecule A), and Q = 0.4050 (15) Å, θ = 64.9 (2)° and φ = 269.3 (2)° (molecule B).

Synthesis and crystallization top

A 60% suspension of sodium hydride in mineral oil (22 mg, 1.55 mmol) was suspended in dry tetra­hydro­furan (10 mL; THF) under argon. La­ctam carbonate (1) (250 mg, 1.0 mmol) dissolved in THF (7 mL) was added drop-wise over 5 mins. The resulting reaction mixture was stirred at room temperature for 6 h. The solvent was removed with a rotary evaporator, and the resulting mixture was poured into saturated ammonium hydroxide (10 mL) and extracted with three 20 mL portions of chloro­form. The chloro­form extracts were combined and washed with saturated NaCl solution (20 mL), and dried over anhydrous Mg2SO4. The solvent was removed and the residue was purified by flash column chromatography (silica gel) with EtOAc as the eluent to yield la­ctam alcohol (3) as a white solid (0.12g, 67%), which was slowly recrystallised from its chloro­form solution (ca 7 days). M.pt: 140-142 °C. 1H NMR (300 MHz, CDCl3): δ 7.20-8.00 (m, 4H, ArH), 7.70 (s, 1H, NH), 2.0-5.0 (m, 5H), 2.02 (s, 1H, OH). 13C NMR (300 MHz): δ 167.0, 137.9, 132.3, 126.0, 127.0, 128.0, 129.0, 65.0, 53.0, 30.0. IR (KBr, cm-1): ν 3684 (OH), 3399, (NH), 1667 (C═O).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. Carbon-bound H-atoms were placed in calculated positions (C—H = 0.93 to 0.99 Å) and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2–1.5Ueq(C). The O-and N-bound H-atoms were refined with O—H = 0.84±0.01 Å and N—H = 0.86±0.01 Å, and with Uiso(H) = 1.5Ueq(O) or 1.2Ueq(N).

Related literature top

For background, including medicinal potential, to compounds related to the title compound, see: Biaggio et al. (2007); Grunewald et al. (1999); Zoretic & Soja (1977). For additional conformational analysis, see: Cremer & Pople (1975).

Structure description top

Referring to Fig. 1, the treatment of la­ctam carbonate (1) with sodium hydride to form compound (2) was unsuccessful and led only to the la­ctam alcohol product (3). Compound (3) might be used as an inter­mediate in organic synthesis. The heterocyclic ring has a screw-boat conformation with puckering parameters (Cremer & Pople, 1975): Puckering Amplitude (Q) = 0.4213 (14) Å, θ = 64.15 (19)° and φ = 271.6 (2)° (molecule A), and Q = 0.4050 (15) Å, θ = 64.9 (2)° and φ = 269.3 (2)° (molecule B).

For background, including medicinal potential, to compounds related to the title compound, see: Biaggio et al. (2007); Grunewald et al. (1999); Zoretic & Soja (1977). For additional conformational analysis, see: Cremer & Pople (1975).

Synthesis and crystallization top

A 60% suspension of sodium hydride in mineral oil (22 mg, 1.55 mmol) was suspended in dry tetra­hydro­furan (10 mL; THF) under argon. La­ctam carbonate (1) (250 mg, 1.0 mmol) dissolved in THF (7 mL) was added drop-wise over 5 mins. The resulting reaction mixture was stirred at room temperature for 6 h. The solvent was removed with a rotary evaporator, and the resulting mixture was poured into saturated ammonium hydroxide (10 mL) and extracted with three 20 mL portions of chloro­form. The chloro­form extracts were combined and washed with saturated NaCl solution (20 mL), and dried over anhydrous Mg2SO4. The solvent was removed and the residue was purified by flash column chromatography (silica gel) with EtOAc as the eluent to yield la­ctam alcohol (3) as a white solid (0.12g, 67%), which was slowly recrystallised from its chloro­form solution (ca 7 days). M.pt: 140-142 °C. 1H NMR (300 MHz, CDCl3): δ 7.20-8.00 (m, 4H, ArH), 7.70 (s, 1H, NH), 2.0-5.0 (m, 5H), 2.02 (s, 1H, OH). 13C NMR (300 MHz): δ 167.0, 137.9, 132.3, 126.0, 127.0, 128.0, 129.0, 65.0, 53.0, 30.0. IR (KBr, cm-1): ν 3684 (OH), 3399, (NH), 1667 (C═O).

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 1. Carbon-bound H-atoms were placed in calculated positions (C—H = 0.93 to 0.99 Å) and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2–1.5Ueq(C). The O-and N-bound H-atoms were refined with O—H = 0.84±0.01 Å and N—H = 0.86±0.01 Å, and with Uiso(H) = 1.5Ueq(O) or 1.2Ueq(N).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMOL (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Reaction scheme for the preparation of the title compound.
[Figure 2] Fig. 2. The molecular structures of the two independent molecules in the title compound showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.
[Figure 3] Fig. 3. Superimposition of the two independent molecules. Molecule A is shown in blue and B in red. The molecules have been superimposed such that the benzene rings are overlapped.
[Figure 4] Fig. 4. A view of the supramolecular chain sustained by O—H···O and N—H···O hydrogen bonds (orange and blue dashed lines, respectively) and aligned along the a axis in the crystal packing.
[Figure 5] Fig. 5. A view in projection down the a axis of the unit-cell contents. The O—H···O, N—H···O and C—H···O interactions are shown as orange, blue and purple dashed lines, respectively.
3-Hydroxymethyl-1,2,3,4-tetrahydroisoquinolin-1-one top
Crystal data top
C10H11NO2Dx = 1.379 Mg m−3
Mr = 177.20Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121Cell parameters from 5937 reflections
a = 6.2846 (1) Åθ = 3.2–74.2°
b = 13.8914 (1) ŵ = 0.79 mm−1
c = 19.5592 (2) ÅT = 100 K
V = 1707.56 (3) Å3Prism, colourless
Z = 80.35 × 0.25 × 0.15 mm
F(000) = 752
Data collection top
Agilent SuperNova CCD
diffractometer		3336 reflections with I > 2σ(I)
Radiation source: SuperNova (Cu) X-ray SourceRint = 0.011
ω scansθmax = 74.3°, θmin = 3.9°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)		h = −7→7
Tmin = 0.882, Tmax = 1.000k = −17→17
6258 measured reflectionsl = −14→24
3358 independent reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.026 w = 1/[σ2(Fo2) + (0.0483P)2 + 0.1971P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.070(Δ/σ)max = 0.001
S = 1.06Δρmax = 0.15 e Å−3
3358 reflectionsΔρmin = −0.29 e Å−3
251 parametersAbsolute structure: Flack x determined using 1359 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
4 restraintsAbsolute structure parameter: −0.05 (6)
Crystal data top
C10H11NO2V = 1707.56 (3) Å3
Mr = 177.20Z = 8
Orthorhombic, P212121Cu Kα radiation
a = 6.2846 (1) ŵ = 0.79 mm−1
b = 13.8914 (1) ÅT = 100 K
c = 19.5592 (2) Å0.35 × 0.25 × 0.15 mm
Data collection top
Agilent SuperNova CCD
diffractometer		3358 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)		3336 reflections with I > 2σ(I)
Tmin = 0.882, Tmax = 1.000Rint = 0.011
6258 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.026H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.070Δρmax = 0.15 e Å−3
S = 1.06Δρmin = −0.29 e Å−3
3358 reflectionsAbsolute structure: Flack x determined using 1359 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
251 parametersAbsolute structure parameter: −0.05 (6)
4 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.62669 (16)0.73762 (7)0.18705 (5)0.0180 (2)
O21.32523 (16)0.66602 (7)0.10231 (5)0.0168 (2)
H2O1.424 (3)0.6888 (18)0.1273 (11)0.049 (7)*
N10.91512 (19)0.75379 (8)0.11906 (6)0.0150 (2)
H1N0.887 (3)0.6996 (10)0.0994 (9)0.021 (5)*
C10.7850 (2)0.78505 (10)0.16823 (6)0.0144 (3)
C20.8387 (2)0.87911 (10)0.20099 (7)0.0156 (3)
C30.6905 (2)0.92359 (11)0.24371 (7)0.0195 (3)
H30.55480.89500.25070.023*
C40.7411 (3)1.00942 (11)0.27601 (8)0.0228 (3)
H40.63971.04010.30470.027*
C50.9411 (3)1.05064 (11)0.26623 (8)0.0212 (3)
H50.97641.10910.28870.025*
C61.0884 (2)1.00671 (10)0.22384 (7)0.0187 (3)
H61.22401.03550.21720.022*
C71.0392 (2)0.92024 (10)0.19065 (7)0.0158 (3)
C81.1995 (2)0.86671 (10)0.14844 (7)0.0169 (3)
H8A1.28100.82260.17840.020*
H8B1.30080.91320.12820.020*
C91.0952 (2)0.80877 (10)0.09148 (7)0.0153 (3)
H91.04050.85440.05610.018*
C101.2538 (2)0.74041 (10)0.05779 (7)0.0163 (3)
H10A1.18630.71080.01720.020*
H10B1.37830.77790.04190.020*
O30.10908 (16)0.52866 (7)−0.04188 (5)0.0200 (2)
O40.80454 (17)0.57641 (7)0.04790 (5)0.0183 (2)
H4O0.904 (3)0.5612 (18)0.0200 (11)0.050 (7)*
N20.3944 (2)0.49397 (8)0.02382 (6)0.0165 (2)
H2N0.373 (4)0.5458 (11)0.0481 (9)0.028 (5)*
C110.2649 (2)0.47641 (10)−0.02887 (7)0.0160 (3)
C120.3141 (2)0.39062 (10)−0.07222 (7)0.0174 (3)
C130.1653 (2)0.35932 (11)−0.12001 (7)0.0217 (3)
H130.03270.3916−0.12420.026*
C140.2107 (3)0.28085 (12)−0.16165 (7)0.0241 (3)
H140.10920.2591−0.19410.029*
C150.4058 (3)0.23446 (11)−0.15537 (8)0.0249 (3)
H150.43700.1805−0.18350.030*
C160.5553 (3)0.26632 (11)−0.10831 (8)0.0230 (3)
H160.68830.2342−0.10470.028*
C170.5124 (2)0.34507 (10)−0.06620 (7)0.0188 (3)
C180.6750 (2)0.38637 (10)−0.01815 (8)0.0208 (3)
H18A0.76100.4350−0.04280.025*
H18B0.77200.3344−0.00310.025*
C190.5744 (2)0.43317 (10)0.04445 (7)0.0179 (3)
H190.51970.38110.07510.022*
C200.7337 (2)0.49417 (10)0.08474 (7)0.0194 (3)
H20A0.66650.51550.12790.023*
H20B0.85830.45390.09660.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0137 (5)0.0198 (5)0.0204 (5)−0.0022 (4)0.0008 (4)−0.0006 (4)
O20.0153 (5)0.0148 (5)0.0203 (5)0.0004 (4)−0.0012 (4)−0.0004 (4)
N10.0141 (5)0.0138 (5)0.0171 (5)−0.0010 (4)−0.0001 (4)−0.0022 (4)
C10.0131 (6)0.0157 (6)0.0145 (6)0.0020 (5)−0.0029 (5)0.0016 (5)
C20.0162 (7)0.0161 (6)0.0146 (6)0.0009 (5)−0.0017 (5)0.0005 (5)
C30.0163 (7)0.0229 (7)0.0193 (6)0.0007 (6)0.0009 (6)−0.0021 (5)
C40.0222 (7)0.0242 (7)0.0219 (7)0.0035 (6)0.0021 (6)−0.0061 (6)
C50.0247 (8)0.0180 (7)0.0210 (7)−0.0005 (6)−0.0045 (6)−0.0050 (5)
C60.0193 (7)0.0172 (6)0.0196 (7)−0.0026 (6)−0.0027 (5)−0.0004 (5)
C70.0170 (7)0.0154 (6)0.0152 (6)0.0011 (5)−0.0021 (5)0.0015 (5)
C80.0131 (6)0.0162 (6)0.0216 (7)−0.0017 (5)0.0005 (6)−0.0017 (5)
C90.0137 (6)0.0153 (6)0.0167 (6)0.0003 (5)0.0015 (5)0.0009 (5)
C100.0158 (6)0.0179 (6)0.0152 (6)0.0013 (5)0.0013 (5)0.0013 (5)
O30.0151 (5)0.0225 (5)0.0225 (5)0.0022 (4)−0.0001 (4)−0.0020 (4)
O40.0162 (5)0.0161 (5)0.0227 (5)−0.0004 (4)0.0016 (4)−0.0021 (4)
N20.0163 (6)0.0150 (5)0.0183 (5)0.0013 (5)0.0003 (5)−0.0032 (4)
C110.0143 (6)0.0167 (6)0.0172 (6)−0.0033 (5)0.0034 (5)0.0004 (5)
C120.0179 (7)0.0169 (6)0.0174 (6)−0.0030 (5)0.0034 (5)−0.0017 (5)
C130.0191 (7)0.0253 (7)0.0206 (7)−0.0040 (6)0.0026 (6)−0.0014 (6)
C140.0275 (8)0.0260 (7)0.0187 (7)−0.0089 (6)0.0018 (6)−0.0036 (6)
C150.0348 (9)0.0187 (6)0.0212 (7)−0.0057 (7)0.0083 (6)−0.0046 (6)
C160.0250 (7)0.0173 (7)0.0267 (7)0.0007 (6)0.0057 (6)−0.0022 (6)
C170.0195 (7)0.0159 (6)0.0210 (6)−0.0020 (5)0.0034 (5)−0.0006 (5)
C180.0156 (7)0.0180 (6)0.0288 (7)0.0018 (5)−0.0001 (6)−0.0040 (6)
C190.0169 (6)0.0153 (6)0.0215 (7)0.0011 (5)−0.0018 (5)0.0019 (5)
C200.0185 (7)0.0200 (6)0.0198 (6)−0.0005 (6)−0.0026 (5)0.0005 (5)
Geometric parameters (Å, º) top
O1—C11.2486 (17)O3—C111.2454 (18)
O2—C101.4239 (16)O4—C201.4220 (17)
O2—H2O0.849 (13)O4—H4O0.855 (13)
N1—C11.3351 (18)N2—C111.3356 (18)
N1—C91.4680 (17)N2—C191.4682 (18)
N1—H1N0.863 (12)N2—H2N0.872 (12)
C1—C21.4939 (18)C11—C121.4949 (18)
C2—C31.396 (2)C12—C131.392 (2)
C2—C71.398 (2)C12—C171.402 (2)
C3—C41.386 (2)C13—C141.390 (2)
C3—H30.9500C13—H130.9500
C4—C51.395 (2)C14—C151.391 (2)
C4—H40.9500C14—H140.9500
C5—C61.385 (2)C15—C161.388 (2)
C5—H50.9500C15—H150.9500
C6—C71.400 (2)C16—C171.396 (2)
C6—H60.9500C16—H160.9500
C7—C81.4997 (19)C17—C181.502 (2)
C8—C91.5227 (18)C18—C191.524 (2)
C8—H8A0.9900C18—H18A0.9900
C8—H8B0.9900C18—H18B0.9900
C9—C101.5263 (19)C19—C201.5303 (19)
C9—H91.0000C19—H191.0000
C10—H10A0.9900C20—H20A0.9900
C10—H10B0.9900C20—H20B0.9900
C10—O2—H2O108.1 (18)C20—O4—H4O110.7 (17)
C1—N1—C9124.60 (12)C11—N2—C19125.20 (12)
C1—N1—H1N118.7 (14)C11—N2—H2N118.6 (14)
C9—N1—H1N116.5 (14)C19—N2—H2N116.2 (14)
O1—C1—N1121.92 (13)O3—C11—N2122.02 (13)
O1—C1—C2121.01 (12)O3—C11—C12120.76 (12)
N1—C1—C2117.06 (12)N2—C11—C12117.21 (12)
C3—C2—C7120.47 (13)C13—C12—C17120.82 (13)
C3—C2—C1119.55 (13)C13—C12—C11119.41 (13)
C7—C2—C1119.94 (12)C17—C12—C11119.73 (13)
C4—C3—C2120.03 (14)C14—C13—C12120.04 (15)
C4—C3—H3120.0C14—C13—H13120.0
C2—C3—H3120.0C12—C13—H13120.0
C3—C4—C5119.83 (14)C13—C14—C15119.50 (14)
C3—C4—H4120.1C13—C14—H14120.3
C5—C4—H4120.1C15—C14—H14120.3
C6—C5—C4120.26 (13)C16—C15—C14120.51 (14)
C6—C5—H5119.9C16—C15—H15119.7
C4—C5—H5119.9C14—C15—H15119.7
C5—C6—C7120.54 (14)C15—C16—C17120.70 (15)
C5—C6—H6119.7C15—C16—H16119.7
C7—C6—H6119.7C17—C16—H16119.7
C2—C7—C6118.86 (13)C16—C17—C12118.42 (14)
C2—C7—C8118.83 (12)C16—C17—C18122.47 (14)
C6—C7—C8122.17 (13)C12—C17—C18119.00 (12)
C7—C8—C9112.08 (12)C17—C18—C19112.53 (12)
C7—C8—H8A109.2C17—C18—H18A109.1
C9—C8—H8A109.2C19—C18—H18A109.1
C7—C8—H8B109.2C17—C18—H18B109.1
C9—C8—H8B109.2C19—C18—H18B109.1
H8A—C8—H8B107.9H18A—C18—H18B107.8
N1—C9—C8109.74 (11)N2—C19—C18110.14 (11)
N1—C9—C10109.78 (11)N2—C19—C20109.10 (11)
C8—C9—C10111.33 (11)C18—C19—C20112.23 (12)
N1—C9—H9108.6N2—C19—H19108.4
C8—C9—H9108.6C18—C19—H19108.4
C10—C9—H9108.6C20—C19—H19108.4
O2—C10—C9113.17 (11)O4—C20—C19112.88 (11)
O2—C10—H10A108.9O4—C20—H20A109.0
C9—C10—H10A108.9C19—C20—H20A109.0
O2—C10—H10B108.9O4—C20—H20B109.0
C9—C10—H10B108.9C19—C20—H20B109.0
H10A—C10—H10B107.8H20A—C20—H20B107.8
C9—N1—C1—O1175.75 (12)C19—N2—C11—O3176.74 (13)
C9—N1—C1—C2−5.26 (19)C19—N2—C11—C12−3.2 (2)
O1—C1—C2—C3−12.24 (19)O3—C11—C12—C13−11.1 (2)
N1—C1—C2—C3168.76 (13)N2—C11—C12—C13168.84 (13)
O1—C1—C2—C7165.51 (12)O3—C11—C12—C17166.40 (13)
N1—C1—C2—C7−13.49 (18)N2—C11—C12—C17−13.68 (19)
C7—C2—C3—C40.3 (2)C17—C12—C13—C141.2 (2)
C1—C2—C3—C4178.05 (13)C11—C12—C13—C14178.68 (13)
C2—C3—C4—C5−0.6 (2)C12—C13—C14—C15−0.4 (2)
C3—C4—C5—C60.7 (2)C13—C14—C15—C16−0.4 (2)
C4—C5—C6—C7−0.4 (2)C14—C15—C16—C170.3 (2)
C3—C2—C7—C60.0 (2)C15—C16—C17—C120.5 (2)
C1—C2—C7—C6−177.76 (12)C15—C16—C17—C18−175.52 (14)
C3—C2—C7—C8175.65 (13)C13—C12—C17—C16−1.3 (2)
C1—C2—C7—C8−2.08 (18)C11—C12—C17—C16−178.75 (13)
C5—C6—C7—C20.1 (2)C13—C12—C17—C18174.88 (13)
C5—C6—C7—C8−175.46 (13)C11—C12—C17—C18−2.57 (19)
C2—C7—C8—C933.21 (17)C16—C17—C18—C19−151.24 (14)
C6—C7—C8—C9−151.25 (13)C12—C17—C18—C1932.74 (18)
C1—N1—C9—C835.96 (18)C11—N2—C19—C1832.98 (18)
C1—N1—C9—C10158.62 (12)C11—N2—C19—C20156.58 (12)
C7—C8—C9—N1−47.52 (15)C17—C18—C19—N2−45.45 (16)
C7—C8—C9—C10−169.26 (11)C17—C18—C19—C20−167.21 (12)
N1—C9—C10—O2−55.30 (15)N2—C19—C20—O4−55.94 (16)
C8—C9—C10—O266.42 (15)C18—C19—C20—O466.41 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O1i0.85 (1)1.86 (1)2.7066 (14)176 (3)
O4—H4O···O3i0.86 (1)1.83 (1)2.6808 (15)178 (3)
N1—H1N···O40.86 (1)2.05 (1)2.9141 (15)176 (2)
N2—H2N···O2ii0.87 (1)2.00 (1)2.8737 (15)179 (2)
C4—H4···O2iii0.952.533.2512 (18)132
C8—H8A···O1i0.992.483.3157 (16)142
C18—H18A···O3i0.992.553.4007 (16)145
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x+2, y+1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O1i0.849 (13)1.859 (13)2.7066 (14)176 (3)
O4—H4O···O3i0.855 (13)1.826 (13)2.6808 (15)178 (3)
N1—H1N···O40.863 (12)2.053 (12)2.9141 (15)175.7 (19)
N2—H2N···O2ii0.872 (12)2.002 (12)2.8737 (15)179.0 (19)
C4—H4···O2iii0.952.533.2512 (18)132
C8—H8A···O1i0.992.483.3157 (16)142
C18—H18A···O3i0.992.553.4007 (16)145
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x+2, y+1/2, −z+1/2.
 

Acknowledgements

The Brazilian agencies CNPq (306121/2013-2 to IC, 117695/2014-9 to CLH and 305626/2013-2 to JZS), CAPES and FAPESP are acknowledged for financial support.

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ISSN: 2056-9890
Volume 71| Part 8| August 2015| Pages o558-o559
https://doi.org/10.1107/S2056989015012670
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