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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1387.
Published online 2009 May 23. doi:  10.1107/S1600536809019011
PMCID: PMC2969554

Triclinic modification of N-[(1,1-di­methyl­ethoxy)carbon­yl]-3-[(R)-prop-2-en-1-ylsulfin­yl]-(R)-alanine ethyl ester at 120 (1) K

Abstract

There are two independent mol­ecules in the asymmetric unit of the title compound, C13H23NO5S. In the crystal structure, inter­molecular N—H(...)O hydrogen bonds link mol­ecules into two independent one-dimensional chains along [100]. The crystal studied was found to be a non-merohedral twin with a ratio of 0.615 (6):0.385 (1) for the refined components. At 200 (1) K [Singh et al. (2009 [triangle]). Acta Cryst. E65, o1385–o1386] the crystal structure of the title compound contains one disordered mol­ecule in the asymmetric unit of a monoclinic unit cell.

Related literature

For the crystal structure of the monlinic modification of the title compound at 200 (1) K and background information, see the preceding paper: Singh et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1387-scheme1.jpg

Experimental

Crystal data

  • C13H23NO5S
  • M r = 305.38
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1387-efi1.jpg
  • a = 5.1483 (5) Å
  • b = 11.6600 (15) Å
  • c = 13.6510 (19) Å
  • α = 88.884 (6)°
  • β = 82.681 (8)°
  • γ = 87.306 (8)°
  • V = 811.81 (17) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.22 mm−1
  • T = 120 K
  • 0.38 × 0.12 × 0.12 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (SORTAV; Blessing, 1995 [triangle]) T min = 0.561, T max = 0.975
  • 4279 measured reflections
  • 4279 independent reflections
  • 3526 reflections with I > 2σ(I)
  • R int = 0.12

Refinement

  • R[F 2 > 2σ(F 2)] = 0.093
  • wR(F 2) = 0.261
  • S = 1.08
  • 4279 reflections
  • 362 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.76 e Å−3
  • Δρmin = −0.50 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1709 Friedel pairs
  • Flack parameter: −0.12 (18)

Data collection: COLLECT (Nonius, 2002 [triangle]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 [triangle]); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019011/hb2979sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019011/hb2979Isup2.hkl

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

Acknowledgments

The authors wish to acknowledge NSERC Canada and the University of Toronto for funding and the donors of the American Chemical Society Petroleum Research Fund for support of this research.

supplementary crystallographic information

Comment

For background information on the title compound see the previous paper (Singh et al., 2009).

The asymmetric unit of the title compound is shown in Fig. 1. It contains two indpendent moleclues [A and B] which have essentially the same conformation apart from the orientation of the propenyl groups (see Fig. 3). This difference is reflected in the the values of the S1—C6—C7—C8 torsion angles for molecules A and B which are -89.5 (13) and 112.2 (13)°, respectively. Data for the title compound were also collected at 200 (1) K and the crystal structure solves and refines in the monoclinic space group P21 (Singh et al., 2009) with one molecule in the asymmetric unit and a disordered propenyl group. The torsion angles for the S1—C6—C7—C8 sequence of atoms in the major and minor components of the disorder are -99 (1) and 107 (3). The same crystal was used for both determinations. In the crystal structure, intermolecular hydrogen bonds link molecules into two independent one-dimensional chains along [100] (Table 1, Fig. 2).

Experimental

For the synthetic procedure, see: Singh et al. (2009).

Refinement

Hydrogen atoms were placed in calculated positions with C—H = 0.95–0.99; N—H = 0.88 Å and refined as riding with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(methyl C). The crystal is a non-merohedral twin: an analysis using PLATON (Spek, 2009) gave the twin law -1 0 0, -0.205 1 - 0.023, 0 0 - 1 with the ratio of twin components being 0.615 (6):0.385 (1).

Figures

Fig. 1.
The asymmetric of (I): displacement elllipsoids are drawn at the 30% probabilty level.
Fig. 2.
Part of the crystal structure of (I) showing hydrogen bonds as dashed lines.
Fig. 3.
Overlay of both independent molecules of the title compound. Molecule A is drawn in black.

Crystal data

C13H23NO5SZ = 2
Mr = 305.38F(000) = 328
Triclinic, P1Dx = 1.249 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.1483 (5) ÅCell parameters from 4279 reflections
b = 11.6600 (15) Åθ = 3.0–25.0°
c = 13.6510 (19) ŵ = 0.22 mm1
α = 88.884 (6)°T = 120 K
β = 82.681 (8)°Needle, colourless
γ = 87.306 (8)°0.38 × 0.12 × 0.12 mm
V = 811.81 (17) Å3

Data collection

Nonius KappaCCD diffractometer4279 independent reflections
Radiation source: fine-focus sealed tube3526 reflections with I > 2σ(I)
graphiteRint = 0.12
Detector resolution: 9 pixels mm-1θmax = 25.0°, θmin = 3.0°
[var phi] scans and ω scans with κ offsetsh = −6→6
Absorption correction: multi-scan (SORTAV; Blessing, 1995)k = −13→13
Tmin = 0.561, Tmax = 0.975l = −15→16
4279 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.093H-atom parameters constrained
wR(F2) = 0.261w = 1/[σ2(Fo2) + (0.1506P)2 + 0.8783P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.003
4279 reflectionsΔρmax = 0.76 e Å3
362 parametersΔρmin = −0.49 e Å3
3 restraintsAbsolute structure: Flack (1983), 1709 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.12 (18)

Special details

Experimental. Absorption correction: multi-scan from symmetry-related measurements (SORTAV; Blessing, 1995)
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S1A0.2491 (4)0.89719 (19)0.70483 (18)0.0441 (7)
O1A0.5083 (12)0.9001 (5)0.7397 (6)0.050 (2)
O2A−0.046 (3)0.6226 (7)0.9264 (8)0.115 (4)
O3A0.1256 (13)0.4856 (5)0.8249 (6)0.0507 (17)
O4A0.7047 (11)0.5997 (5)0.6652 (5)0.0413 (15)
O5A0.4606 (12)0.5281 (6)0.5530 (5)0.0463 (16)
N1A0.2589 (14)0.6302 (6)0.6753 (6)0.0383 (18)
H1AC0.12450.63030.64150.046*
C1A0.0703 (18)0.7904 (8)0.7809 (8)0.042 (2)
H1AA0.04120.81580.85040.051*
H1AB−0.10310.78210.75830.051*
C2A0.2212 (19)0.6762 (8)0.7748 (8)0.042 (2)
H2AA0.39900.68920.79340.051*
C3A0.088 (2)0.5935 (8)0.8518 (9)0.051 (3)
C4A−0.010 (2)0.3966 (9)0.8887 (8)0.045 (2)
H4AA0.10430.32590.88860.054*
H4AB−0.04650.42430.95740.054*
C5A−0.256 (2)0.3713 (10)0.8523 (8)0.052 (3)
H5AA−0.34350.31200.89430.078*
H5AB−0.21860.34380.78430.078*
H5AC−0.36940.44120.85370.078*
C6A0.058 (2)1.0212 (9)0.7578 (10)0.053 (3)
H6AA−0.13031.01010.75600.063*
H6AB0.08701.02860.82770.063*
C7A0.135 (2)1.1285 (9)0.7021 (10)0.060 (3)
H7A0.04291.15080.64830.072*
C8A0.317 (3)1.1927 (11)0.7218 (13)0.081 (4)
H8A10.41371.17300.77500.097*
H8A20.35541.25980.68310.097*
C9A0.4911 (15)0.5880 (7)0.6343 (7)0.0332 (19)
C10A0.6878 (18)0.4846 (8)0.4849 (7)0.045 (2)
C11A0.558 (2)0.4260 (10)0.4071 (9)0.057 (3)
H11A0.45710.48320.37230.086*
H11B0.44120.36850.43870.086*
H11C0.69330.38820.35980.086*
C12A0.849 (2)0.5805 (8)0.4435 (8)0.051 (3)
H12A0.73950.63560.40980.077*
H12B0.99410.55040.39640.077*
H12C0.91830.61900.49710.077*
C13A0.846 (2)0.3923 (9)0.5393 (9)0.052 (3)
H13A0.92970.42910.59040.077*
H13B0.98120.35500.49180.077*
H13C0.72770.33480.57000.077*
S1B0.1520 (4)0.40207 (18)0.18589 (17)0.0407 (6)
O1B−0.1088 (12)0.4057 (5)0.1524 (5)0.0425 (17)
O2B0.467 (2)0.1249 (6)−0.0308 (7)0.084 (3)
O3B0.3134 (13)−0.0110 (5)0.0748 (5)0.0487 (17)
O4B−0.2688 (11)0.1054 (5)0.2279 (5)0.0411 (15)
O5B−0.0182 (11)0.0315 (6)0.3428 (5)0.0444 (16)
N1B0.1704 (14)0.1343 (6)0.2209 (6)0.0372 (18)
H1BC0.30290.13400.25570.045*
C1B0.3469 (17)0.2925 (8)0.1143 (8)0.041 (2)
H1BA0.38310.31860.04470.050*
H1BB0.51670.27890.14040.050*
C2B0.2017 (18)0.1810 (8)0.1194 (8)0.041 (2)
H2BA0.02310.19860.10000.050*
C3B0.342 (2)0.0972 (8)0.0474 (8)0.047 (2)
C4B0.455 (2)−0.1020 (9)0.0122 (10)0.054 (3)
H4BA0.4769−0.0765−0.05790.065*
H4BB0.3548−0.17270.01790.065*
C5B0.718 (2)−0.1254 (10)0.0464 (9)0.059 (3)
H5BA0.8162−0.18500.00550.089*
H5BB0.6947−0.15150.11550.089*
H5BC0.8158−0.05490.04070.089*
C6B0.322 (2)0.5239 (8)0.1283 (9)0.045 (2)
H6BA0.50680.51930.14140.054*
H6BB0.31980.52240.05590.054*
C7B0.190 (2)0.6333 (9)0.1687 (10)0.056 (3)
H7B0.01910.65280.15290.067*
C8B0.293 (3)0.7024 (11)0.2231 (11)0.071 (4)
H8B10.46390.68560.24030.086*
H8B20.19800.77050.24620.086*
C9B−0.0584 (16)0.0921 (7)0.2610 (7)0.035 (2)
C10B−0.2460 (17)−0.0139 (8)0.4090 (8)0.044 (2)
C11B−0.107 (2)−0.0749 (11)0.4897 (9)0.061 (3)
H11D−0.0214−0.01820.52530.092*
H11E0.0257−0.13100.45930.092*
H11F−0.2352−0.11450.53590.092*
C12B−0.4219 (18)0.0843 (9)0.4501 (8)0.052 (3)
H12D−0.50830.12140.39710.078*
H12E−0.31770.14020.47870.078*
H12F−0.55470.05570.50140.078*
C13B−0.3820 (19)−0.1009 (8)0.3539 (8)0.047 (3)
H13D−0.4722−0.06110.30310.070*
H13E−0.5098−0.14040.40040.070*
H13F−0.2514−0.15710.32260.070*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S1A0.0443 (15)0.0370 (13)0.0497 (18)0.0002 (10)−0.0016 (12)−0.0016 (11)
O1A0.034 (4)0.035 (4)0.078 (6)0.003 (3)0.000 (4)−0.011 (3)
O2A0.223 (12)0.033 (4)0.065 (7)0.014 (5)0.062 (8)0.006 (4)
O3A0.055 (4)0.038 (4)0.058 (5)−0.005 (3)−0.003 (3)−0.007 (3)
O4A0.035 (3)0.040 (3)0.049 (4)−0.001 (3)−0.006 (3)−0.003 (3)
O5A0.041 (4)0.055 (4)0.043 (4)−0.004 (3)−0.003 (3)−0.015 (3)
N1A0.034 (4)0.046 (4)0.036 (5)0.002 (3)−0.011 (3)0.001 (4)
C1A0.036 (5)0.045 (5)0.045 (6)0.000 (4)−0.003 (4)0.002 (5)
C2A0.050 (6)0.034 (5)0.043 (6)0.001 (4)−0.008 (4)−0.003 (4)
C3A0.058 (6)0.043 (6)0.049 (7)0.003 (4)−0.003 (5)0.008 (5)
C4A0.046 (6)0.050 (6)0.040 (6)−0.002 (4)−0.004 (5)0.005 (5)
C5A0.060 (7)0.059 (6)0.039 (6)−0.019 (5)−0.010 (5)0.019 (5)
C6A0.055 (6)0.038 (5)0.064 (8)−0.004 (4)−0.003 (5)−0.001 (5)
C7A0.057 (7)0.051 (7)0.071 (9)−0.007 (5)0.001 (6)−0.012 (6)
C8A0.073 (8)0.061 (8)0.105 (12)−0.016 (6)0.016 (8)−0.019 (8)
C9A0.029 (5)0.028 (4)0.043 (6)−0.001 (3)−0.009 (4)0.006 (4)
C10A0.043 (5)0.045 (5)0.044 (6)0.002 (4)−0.001 (4)−0.001 (4)
C11A0.044 (6)0.083 (8)0.044 (7)0.004 (5)−0.004 (5)−0.021 (6)
C12A0.054 (6)0.043 (5)0.056 (7)0.001 (4)−0.001 (5)0.003 (5)
C13A0.046 (6)0.045 (6)0.061 (8)−0.001 (4)0.006 (5)−0.004 (5)
S1B0.0410 (14)0.0346 (13)0.0462 (17)−0.0050 (9)−0.0031 (11)0.0014 (10)
O1B0.039 (4)0.035 (4)0.053 (5)−0.005 (3)−0.004 (3)0.002 (3)
O2B0.151 (9)0.035 (4)0.057 (6)−0.020 (4)0.034 (6)0.001 (4)
O3B0.056 (4)0.035 (4)0.053 (5)0.002 (3)−0.001 (3)−0.002 (3)
O4B0.033 (3)0.043 (4)0.047 (4)−0.003 (3)−0.006 (3)0.008 (3)
O5B0.038 (4)0.051 (4)0.045 (4)−0.008 (3)−0.006 (3)0.009 (3)
N1B0.032 (4)0.045 (4)0.036 (5)−0.009 (3)−0.008 (3)−0.002 (4)
C1B0.031 (5)0.042 (5)0.051 (7)−0.002 (4)−0.003 (4)−0.004 (5)
C2B0.035 (5)0.035 (5)0.055 (7)−0.005 (4)−0.007 (4)0.003 (4)
C3B0.054 (6)0.035 (5)0.052 (7)−0.006 (4)−0.011 (5)0.004 (5)
C4B0.074 (7)0.027 (5)0.059 (8)−0.003 (4)0.005 (6)0.000 (5)
C5B0.060 (7)0.054 (6)0.061 (8)0.010 (5)−0.002 (5)−0.015 (6)
C6B0.040 (5)0.040 (5)0.054 (7)−0.006 (4)−0.002 (4)−0.002 (4)
C7B0.049 (6)0.045 (6)0.073 (9)−0.006 (5)−0.003 (6)−0.001 (6)
C8B0.066 (7)0.050 (7)0.094 (11)−0.009 (5)0.008 (7)−0.009 (7)
C9B0.034 (5)0.031 (4)0.039 (6)−0.005 (3)−0.001 (4)0.003 (4)
C10B0.042 (5)0.044 (5)0.044 (6)−0.005 (4)−0.002 (4)0.005 (4)
C11B0.054 (6)0.077 (8)0.050 (7)−0.013 (5)0.002 (5)0.017 (6)
C12B0.042 (5)0.063 (7)0.049 (7)−0.011 (5)0.003 (5)−0.013 (5)
C13B0.048 (6)0.043 (6)0.048 (7)−0.006 (4)0.000 (5)0.005 (5)

Geometric parameters (Å, °)

S1A—O1A1.475 (7)S1B—O1B1.471 (7)
S1A—C1A1.814 (10)S1B—C1B1.809 (10)
S1A—C6A1.818 (11)S1B—C6B1.816 (11)
O2A—C3A1.200 (14)O2B—C3B1.220 (13)
O3A—C3A1.316 (12)O3B—C3B1.319 (12)
O3A—C4A1.483 (13)O3B—C4B1.481 (13)
O4A—C9A1.241 (10)O4B—C9B1.228 (10)
O5A—C9A1.353 (11)O5B—C9B1.344 (11)
O5A—C10A1.475 (11)O5B—C10B1.497 (11)
N1A—C9A1.330 (11)N1B—C9B1.345 (11)
N1A—C2A1.456 (13)N1B—C2B1.471 (13)
N1A—H1AC0.8800N1B—H1BC0.8800
C1A—C2A1.508 (12)C1B—C2B1.526 (13)
C1A—H1AA0.9900C1B—H1BA0.9900
C1A—H1AB0.9900C1B—H1BB0.9900
C2A—C3A1.532 (15)C2B—C3B1.495 (14)
C2A—H2AA1.0000C2B—H2BA1.0000
C4A—C5A1.461 (14)C4B—C5B1.500 (16)
C4A—H4AA0.9900C4B—H4BA0.9900
C4A—H4AB0.9900C4B—H4BB0.9900
C5A—H5AA0.9800C5B—H5BA0.9800
C5A—H5AB0.9800C5B—H5BB0.9800
C5A—H5AC0.9800C5B—H5BC0.9800
C6A—C7A1.494 (17)C6B—C7B1.497 (14)
C6A—H6AA0.9900C6B—H6BA0.9900
C6A—H6AB0.9900C6B—H6BB0.9900
C7A—C8A1.283 (17)C7B—C8B1.282 (17)
C7A—H7A0.9500C7B—H7B0.9500
C8A—H8A10.9500C8B—H8B10.9500
C8A—H8A20.9500C8B—H8B20.9500
C10A—C12A1.483 (14)C10B—C12B1.498 (13)
C10A—C11A1.513 (14)C10B—C13B1.521 (14)
C10A—C13A1.554 (14)C10B—C11B1.535 (15)
C11A—H11A0.9800C11B—H11D0.9800
C11A—H11B0.9800C11B—H11E0.9800
C11A—H11C0.9800C11B—H11F0.9800
C12A—H12A0.9800C12B—H12D0.9800
C12A—H12B0.9800C12B—H12E0.9800
C12A—H12C0.9800C12B—H12F0.9800
C13A—H13A0.9800C13B—H13D0.9800
C13A—H13B0.9800C13B—H13E0.9800
C13A—H13C0.9800C13B—H13F0.9800
O1A—S1A—C1A106.2 (4)O1B—S1B—C1B106.4 (4)
O1A—S1A—C6A106.3 (5)O1B—S1B—C6B106.8 (4)
C1A—S1A—C6A96.2 (5)C1B—S1B—C6B96.5 (5)
C3A—O3A—C4A118.2 (8)C3B—O3B—C4B118.7 (8)
C9A—O5A—C10A121.6 (7)C9B—O5B—C10B120.0 (6)
C9A—N1A—C2A121.8 (8)C9B—N1B—C2B120.8 (8)
C9A—N1A—H1AC119.1C9B—N1B—H1BC119.6
C2A—N1A—H1AC119.1C2B—N1B—H1BC119.6
C2A—C1A—S1A110.4 (7)C2B—C1B—S1B110.2 (6)
C2A—C1A—H1AA109.6C2B—C1B—H1BA109.6
S1A—C1A—H1AA109.6S1B—C1B—H1BA109.6
C2A—C1A—H1AB109.6C2B—C1B—H1BB109.6
S1A—C1A—H1AB109.6S1B—C1B—H1BB109.6
H1AA—C1A—H1AB108.1H1BA—C1B—H1BB108.1
N1A—C2A—C1A112.7 (8)N1B—C2B—C3B112.1 (8)
N1A—C2A—C3A113.1 (8)N1B—C2B—C1B110.4 (8)
C1A—C2A—C3A109.1 (8)C3B—C2B—C1B109.9 (8)
N1A—C2A—H2AA107.2N1B—C2B—H2BA108.1
C1A—C2A—H2AA107.2C3B—C2B—H2BA108.1
C3A—C2A—H2AA107.2C1B—C2B—H2BA108.1
O2A—C3A—O3A123.0 (10)O2B—C3B—O3B122.5 (10)
O2A—C3A—C2A124.6 (9)O2B—C3B—C2B123.8 (9)
O3A—C3A—C2A112.3 (9)O3B—C3B—C2B113.6 (9)
C5A—C4A—O3A109.9 (8)O3B—C4B—C5B108.1 (9)
C5A—C4A—H4AA109.7O3B—C4B—H4BA110.1
O3A—C4A—H4AA109.7C5B—C4B—H4BA110.1
C5A—C4A—H4AB109.7O3B—C4B—H4BB110.1
O3A—C4A—H4AB109.7C5B—C4B—H4BB110.1
H4AA—C4A—H4AB108.2H4BA—C4B—H4BB108.4
C4A—C5A—H5AA109.5C4B—C5B—H5BA109.5
C4A—C5A—H5AB109.5C4B—C5B—H5BB109.5
H5AA—C5A—H5AB109.5H5BA—C5B—H5BB109.5
C4A—C5A—H5AC109.5C4B—C5B—H5BC109.5
H5AA—C5A—H5AC109.5H5BA—C5B—H5BC109.5
H5AB—C5A—H5AC109.5H5BB—C5B—H5BC109.5
C7A—C6A—S1A110.9 (8)C7B—C6B—S1B109.7 (8)
C7A—C6A—H6AA109.5C7B—C6B—H6BA109.7
S1A—C6A—H6AA109.5S1B—C6B—H6BA109.7
C7A—C6A—H6AB109.5C7B—C6B—H6BB109.7
S1A—C6A—H6AB109.5S1B—C6B—H6BB109.7
H6AA—C6A—H6AB108.1H6BA—C6B—H6BB108.2
C8A—C7A—C6A124.6 (14)C8B—C7B—C6B124.5 (11)
C8A—C7A—H7A117.7C8B—C7B—H7B117.8
C6A—C7A—H7A117.7C6B—C7B—H7B117.8
C7A—C8A—H8A1120.0C7B—C8B—H8B1120.0
C7A—C8A—H8A2120.0C7B—C8B—H8B2120.0
H8A1—C8A—H8A2120.0H8B1—C8B—H8B2120.0
O4A—C9A—N1A126.2 (8)O4B—C9B—O5B125.5 (7)
O4A—C9A—O5A124.3 (7)O4B—C9B—N1B125.9 (8)
N1A—C9A—O5A109.5 (7)O5B—C9B—N1B108.7 (7)
O5A—C10A—C12A110.6 (7)O5B—C10B—C12B109.5 (7)
O5A—C10A—C11A102.4 (7)O5B—C10B—C13B109.9 (8)
C12A—C10A—C11A112.5 (9)C12B—C10B—C13B114.2 (8)
O5A—C10A—C13A109.3 (8)O5B—C10B—C11B101.2 (7)
C12A—C10A—C13A113.0 (8)C12B—C10B—C11B111.3 (9)
C11A—C10A—C13A108.6 (9)C13B—C10B—C11B110.0 (9)
C10A—C11A—H11A109.5C10B—C11B—H11D109.5
C10A—C11A—H11B109.5C10B—C11B—H11E109.5
H11A—C11A—H11B109.5H11D—C11B—H11E109.5
C10A—C11A—H11C109.5C10B—C11B—H11F109.5
H11A—C11A—H11C109.5H11D—C11B—H11F109.5
H11B—C11A—H11C109.5H11E—C11B—H11F109.5
C10A—C12A—H12A109.5C10B—C12B—H12D109.5
C10A—C12A—H12B109.5C10B—C12B—H12E109.5
H12A—C12A—H12B109.5H12D—C12B—H12E109.5
C10A—C12A—H12C109.5C10B—C12B—H12F109.5
H12A—C12A—H12C109.5H12D—C12B—H12F109.5
H12B—C12A—H12C109.5H12E—C12B—H12F109.5
C10A—C13A—H13A109.5C10B—C13B—H13D109.5
C10A—C13A—H13B109.5C10B—C13B—H13E109.5
H13A—C13A—H13B109.5H13D—C13B—H13E109.5
C10A—C13A—H13C109.5C10B—C13B—H13F109.5
H13A—C13A—H13C109.5H13D—C13B—H13F109.5
H13B—C13A—H13C109.5H13E—C13B—H13F109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1A—H1AC···O4Ai0.882.192.913 (9)139
N1B—H1BC···O4Bii0.882.202.904 (9)137

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2979).

References

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