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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o379.
Published online 2008 January 9. doi:  10.1107/S1600536807068195
PMCID: PMC2960228

4-Nitro­phenyl α-l-rhamnopyran­oside hemihydrate

Abstract

In the title compound, C12H15NO7·0.5H2O, there are two independent mol­ecules in the asymmetric unit, together with one water molecule. The pyran­oside rings each have close to a 1 C 4 chair conformation and the nitro groups are almost coplanar with the benzene rings. The water mol­ecule links the two independent mol­ecules through O—H(...)O hydrogen bonds. All the hydroxyl groups are involved in hydrogen-bond inter­actions, giving rise to a three-dimensional network.

Related literature

For a related structure, see Fernandez-Castaño & Foces-Foces (1996 [triangle]). For related literature, see: Garegg et al. (1978 [triangle]).

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Object name is e-64-0o379-scheme1.jpg

Experimental

Crystal data

  • C12H15NO7·0.5H2O
  • M r = 294.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o379-efi1.jpg
  • a = 10.5371 (15) Å
  • b = 6.8681 (8) Å
  • c = 19.135 (3) Å
  • β = 101.543 (7)°
  • V = 1356.8 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.12 mm−1
  • T = 100 (2) K
  • 0.6 × 0.58 × 0.23 mm

Data collection

  • Bruker APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2002 [triangle]) T min = 0.923, T max = 0.972
  • 14281 measured reflections
  • 3340 independent reflections
  • 3147 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.080
  • S = 1.04
  • 3340 reflections
  • 396 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1995 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068195/bv2086sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068195/bv2086Isup2.hkl

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

Acknowledgments

PP is grateful to the Région Bretagne for a grant.

supplementary crystallographic information

Comment

α-L-Rhamnosidases (E.C. 3.2.1.40) catalyze the hydrolysis of L-rhamnose from polysaccharides and glycosides. During in vitro studies, the activity of these enzymes is determined most of the time using the title compound, (I), following the amount of p-nitrophenolate ions released by monitoring the emmision at 400 nm.

The stucture of (I) is shown in Fig. 1. The molecular packing (Fig. 2) is stabilized by hydrogen bonds between all the hydroxyl groups and the water molecules.

Experimental

The title compound is commercialy available (Sigma Chemical Company) or can be easily prepared following the described procedure of Garegg et al. (1978). The title compound, (I), was crystallized from methanol by slow evaporation of the solvent.

Refinement

In the absence of significant anomalous scattering effects, Friedel pairs were merged. The positional and displacement parameters for the H atoms bound to O were refined. The methyl H atoms were constrained to an ideal geometry, with C—H = 0.98Å and Uiso(H) = 1.5Ueq(C), but each group was allowed to rotate freely about its C—C bond. All other H atoms were placed in calculated positions (C—H = 0.95–1.00 Å), with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure and atom-labelling scheme for (I). Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
The crystal packing of the structure, showing the network of hydrogen bonds (dotted lines).

Crystal data

C12H15NO7·0.5H2OF000 = 620
Mr = 294.26Dx = 1.441 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 8274 reflections
a = 10.5371 (15) Åθ = 2.4–27.4º
b = 6.8681 (8) ŵ = 0.12 mm1
c = 19.135 (3) ÅT = 100 (2) K
β = 101.543 (7)ºPlate, colourless
V = 1356.8 (3) Å30.6 × 0.58 × 0.23 mm
Z = 4

Data collection

Bruker APEXII diffractometer3147 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.051
T = 100(2) Kθmax = 27.4º
CCD rotation images, thin slices scansθmin = 3.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 2002)h = −13→12
Tmin = 0.923, Tmax = 0.972k = −8→8
14281 measured reflectionsl = −24→21
3340 independent 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)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.080  w = 1/[σ2(Fo2) + (0.0398P)2 + 0.2743P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3340 reflectionsΔρmax = 0.38 e Å3
396 parametersΔρmin = −0.24 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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
N1130.06897 (18)1.3356 (3)−0.12305 (9)0.0208 (4)
O114−0.04061 (15)1.3222 (3)−0.16072 (8)0.0285 (4)
O1150.16860 (16)1.3419 (3)−0.14777 (8)0.0320 (4)
C1100.0816 (2)1.3456 (3)−0.04511 (10)0.0169 (4)
C109−0.0304 (2)1.3374 (3)−0.01675 (11)0.0181 (4)
H109−0.11321.326−0.04710.022*
C108−0.01818 (19)1.3462 (3)0.05646 (11)0.0176 (4)
H108−0.09331.34030.07680.021*
C1070.10436 (19)1.3638 (3)0.10079 (10)0.0154 (4)
C1120.21624 (19)1.3726 (3)0.07163 (11)0.0184 (4)
H1120.29921.38490.10180.022*
C1110.20393 (19)1.3632 (3)−0.00206 (11)0.0179 (4)
H1110.27861.3688−0.02280.021*
O1010.10387 (13)1.3698 (2)0.17252 (7)0.0173 (3)
C1010.21582 (18)1.4443 (3)0.22070 (10)0.0150 (4)
H1010.23871.5740.2030.018*
C1020.17225 (19)1.4730 (3)0.29214 (10)0.0143 (4)
H1020.09051.5510.28480.017*
O1020.27280 (15)1.5708 (2)0.34038 (8)0.0188 (3)
H120.259 (3)1.692 (6)0.3366 (17)0.05*
C1030.15121 (19)1.2737 (3)0.32381 (10)0.0136 (4)
H1030.07811.20650.29140.016*
O1030.11609 (15)1.3034 (2)0.39202 (7)0.0180 (3)
H130.115 (3)1.197 (6)0.4126 (18)0.05*
C1040.2735 (2)1.1506 (3)0.32928 (10)0.0136 (4)
H1040.34751.21510.36190.016*
O1040.25457 (15)0.9597 (2)0.35459 (8)0.0173 (3)
H140.246 (3)0.959 (6)0.3956 (19)0.05*
C1050.30432 (19)1.1288 (3)0.25488 (11)0.0151 (4)
H1050.22971.06410.22280.018*
C1060.4262 (2)1.0144 (3)0.25400 (12)0.0232 (5)
H10A0.44251.01120.20540.035*
H10B0.41570.88110.27030.035*
H10C0.49951.07640.28580.035*
O1050.32371 (13)1.3205 (2)0.22692 (7)0.0154 (3)
N213−0.39091 (16)0.4276 (3)0.01163 (9)0.0194 (4)
O215−0.32520 (14)0.3120 (3)−0.01531 (8)0.0235 (3)
O214−0.46481 (17)0.5465 (3)−0.02365 (8)0.0322 (4)
C210−0.38055 (19)0.4233 (3)0.08925 (10)0.0168 (4)
C209−0.4304 (2)0.5769 (3)0.12271 (11)0.0190 (4)
H209−0.47240.68270.09550.023*
C208−0.41803 (19)0.5738 (3)0.19635 (11)0.0180 (4)
H208−0.45040.67870.22010.022*
C207−0.35783 (18)0.4156 (3)0.23528 (10)0.0146 (4)
C212−0.3100 (2)0.2609 (3)0.20071 (11)0.0180 (4)
H212−0.26990.15320.22760.022*
C211−0.32092 (19)0.2644 (3)0.12718 (11)0.0178 (4)
H211−0.28830.16020.10330.021*
O201−0.34096 (13)0.3963 (2)0.30809 (7)0.0153 (3)
C201−0.37263 (19)0.5583 (3)0.34905 (10)0.0141 (4)
H201−0.46770.58470.33530.017*
C202−0.34018 (18)0.4911 (3)0.42743 (10)0.0139 (4)
H202−0.38270.3630.43230.017*
O202−0.38516 (14)0.6325 (2)0.47115 (8)0.0168 (3)
H22−0.464 (3)0.597 (6)0.4737 (17)0.05*
C203−0.19271 (18)0.4703 (3)0.45089 (10)0.0122 (4)
H203−0.16360.3550.42630.015*
O203−0.16051 (13)0.4396 (2)0.52635 (7)0.0148 (3)
H23−0.114 (3)0.341 (6)0.5351 (17)0.05*
C204−0.12210 (17)0.6509 (3)0.43223 (10)0.0123 (4)
H204−0.14530.76230.46090.015*
O2040.01541 (13)0.6233 (2)0.45107 (7)0.0149 (3)
H240.036 (3)0.533 (6)0.4294 (18)0.05*
C206−0.1076 (2)0.8921 (3)0.33282 (11)0.0202 (4)
H20A−0.13670.91480.28150.03*
H20B−0.01280.88430.34430.03*
H20C−0.13650.99970.35950.03*
C205−0.16438 (18)0.7030 (3)0.35314 (10)0.0131 (4)
H205−0.13980.59480.32340.016*
O205−0.30423 (13)0.7267 (2)0.33721 (7)0.0142 (3)
O10.62208 (15)0.0270 (2)0.50941 (9)0.0203 (3)
H1A0.628 (3)−0.084 (6)0.4891 (18)0.05*
H1B0.664 (3)0.021 (6)0.5520 (19)0.05*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N1130.0260 (9)0.0160 (8)0.0201 (9)−0.0018 (7)0.0036 (7)−0.0005 (7)
O1140.0280 (8)0.0352 (9)0.0194 (7)−0.0047 (7)−0.0025 (6)−0.0013 (7)
O1150.0295 (9)0.0478 (11)0.0201 (8)−0.0030 (8)0.0083 (7)−0.0006 (8)
C1100.0221 (10)0.0125 (9)0.0154 (9)−0.0003 (8)0.0023 (8)0.0008 (7)
C1090.0173 (10)0.0138 (9)0.0216 (10)−0.0015 (8)0.0003 (7)−0.0003 (8)
C1080.0162 (9)0.0151 (9)0.0222 (10)−0.0013 (8)0.0057 (8)0.0005 (8)
C1070.0174 (9)0.0125 (9)0.0163 (9)0.0001 (8)0.0030 (7)0.0007 (7)
C1120.0153 (9)0.0205 (10)0.0185 (10)−0.0014 (8)0.0014 (7)0.0014 (8)
C1110.0184 (10)0.0166 (10)0.0195 (10)−0.0010 (8)0.0056 (8)0.0022 (8)
O1010.0152 (7)0.0213 (7)0.0151 (7)−0.0021 (6)0.0026 (5)0.0011 (6)
C1010.0138 (9)0.0137 (9)0.0169 (9)−0.0009 (7)0.0019 (7)0.0010 (7)
C1020.0155 (9)0.0105 (8)0.0160 (9)0.0034 (7)0.0010 (7)0.0014 (7)
O1020.0267 (8)0.0091 (6)0.0192 (7)0.0000 (6)0.0010 (6)−0.0003 (5)
C1030.0157 (9)0.0122 (8)0.0135 (9)−0.0005 (7)0.0039 (7)−0.0007 (7)
O1030.0260 (8)0.0131 (7)0.0170 (7)0.0042 (6)0.0097 (6)0.0012 (6)
C1040.0168 (9)0.0079 (8)0.0166 (9)0.0004 (7)0.0045 (7)0.0003 (7)
O1040.0280 (8)0.0092 (6)0.0171 (7)0.0004 (6)0.0105 (6)0.0006 (5)
C1050.0173 (10)0.0111 (8)0.0183 (10)−0.0007 (8)0.0067 (7)−0.0004 (7)
C1060.0255 (11)0.0168 (10)0.0317 (12)0.0061 (8)0.0163 (9)0.0045 (9)
O1050.0153 (7)0.0131 (6)0.0189 (7)0.0008 (5)0.0057 (5)0.0033 (5)
N2130.0159 (8)0.0243 (9)0.0178 (8)−0.0008 (7)0.0029 (7)−0.0022 (7)
O2150.0200 (7)0.0317 (8)0.0196 (7)0.0015 (7)0.0057 (6)−0.0045 (7)
O2140.0348 (9)0.0422 (10)0.0171 (8)0.0156 (8)−0.0009 (6)0.0026 (7)
C2100.0132 (9)0.0226 (10)0.0139 (9)−0.0016 (8)0.0012 (7)−0.0024 (8)
C2090.0160 (10)0.0201 (10)0.0190 (10)0.0038 (8)−0.0008 (8)0.0002 (8)
C2080.0161 (10)0.0176 (9)0.0194 (10)0.0042 (8)0.0013 (8)−0.0018 (8)
C2070.0120 (9)0.0158 (9)0.0150 (9)−0.0021 (7)0.0001 (7)−0.0034 (7)
C2120.0174 (9)0.0155 (9)0.0199 (10)0.0024 (8)0.0006 (8)−0.0006 (8)
C2110.0165 (10)0.0189 (10)0.0179 (10)0.0019 (8)0.0035 (8)−0.0046 (8)
O2010.0176 (7)0.0136 (7)0.0136 (7)0.0015 (6)0.0008 (5)−0.0013 (5)
C2010.0128 (9)0.0138 (9)0.0152 (9)0.0001 (8)0.0013 (7)−0.0033 (7)
C2020.0127 (9)0.0130 (9)0.0162 (9)0.0000 (7)0.0031 (7)−0.0021 (7)
O2020.0157 (7)0.0159 (7)0.0197 (7)0.0000 (6)0.0061 (6)−0.0038 (6)
C2030.0143 (9)0.0118 (8)0.0102 (8)0.0014 (7)0.0014 (7)0.0001 (7)
O2030.0185 (7)0.0143 (7)0.0114 (6)0.0026 (6)0.0027 (5)0.0018 (5)
C2040.0102 (8)0.0124 (8)0.0141 (9)0.0011 (7)0.0017 (7)−0.0005 (7)
O2040.0110 (6)0.0140 (7)0.0185 (7)0.0012 (5)0.0005 (5)−0.0024 (6)
C2060.0226 (10)0.0194 (10)0.0169 (10)−0.0050 (9)0.0001 (8)0.0052 (8)
C2050.0123 (9)0.0135 (8)0.0130 (9)0.0011 (7)0.0016 (7)0.0003 (7)
O2050.0127 (7)0.0133 (7)0.0155 (7)0.0011 (5)0.0003 (5)0.0011 (5)
O10.0191 (7)0.0178 (8)0.0238 (8)0.0025 (6)0.0032 (6)−0.0006 (6)

Geometric parameters (Å, °)

N113—O1151.236 (2)N213—O2151.232 (2)
N113—O1141.236 (2)N213—C2101.468 (3)
N113—C1101.472 (3)C210—C2111.389 (3)
C110—C1111.389 (3)C210—C2091.390 (3)
C110—C1091.395 (3)C209—C2081.389 (3)
C109—C1081.382 (3)C209—H2090.95
C109—H1090.95C208—C2071.396 (3)
C108—C1071.401 (3)C208—H2080.95
C108—H1080.95C207—O2011.375 (2)
C107—O1011.374 (2)C207—C2121.398 (3)
C107—C1121.403 (3)C212—C2111.389 (3)
C112—C1111.391 (3)C212—H2120.95
C112—H1120.95C211—H2110.95
C111—H1110.95O201—C2011.438 (2)
O101—C1011.438 (2)C201—O2051.405 (2)
C101—O1051.406 (2)C201—C2021.541 (3)
C101—C1021.539 (3)C201—H2011
C101—H1011C202—O2021.424 (2)
C102—O1021.426 (2)C202—C2031.535 (3)
C102—C1031.531 (3)C202—H2021
C102—H1021O202—H220.88 (3)
O102—H120.85 (4)C203—O2031.431 (2)
C103—O1031.440 (2)C203—C2041.525 (3)
C103—C1041.527 (3)C203—H2031
C103—H1031O203—H230.84 (4)
O103—H130.83 (4)C204—O2041.434 (2)
C104—O1041.426 (2)C204—C2051.532 (3)
C104—C1051.530 (3)C204—H2041
C104—H1041O204—H240.80 (4)
O104—H140.81 (4)C206—C2051.513 (3)
C105—O1051.450 (2)C206—H20A0.98
C105—C1061.508 (3)C206—H20B0.98
C105—H1051C206—H20C0.98
C106—H10A0.98C205—O2051.453 (2)
C106—H10B0.98C205—H2051
C106—H10C0.98O1—H1A0.86 (4)
N213—O2141.232 (2)O1—H1B0.85 (4)
O115—N113—O114123.06 (18)O214—N213—C210118.61 (17)
O115—N113—C110118.34 (17)O215—N213—C210118.43 (17)
O114—N113—C110118.61 (17)C211—C210—C209121.90 (18)
C111—C110—C109121.97 (19)C211—C210—N213118.60 (18)
C111—C110—N113119.34 (18)C209—C210—N213119.49 (18)
C109—C110—N113118.69 (17)C208—C209—C210119.23 (19)
C108—C109—C110118.56 (18)C208—C209—H209120.4
C108—C109—H109120.7C210—C209—H209120.4
C110—C109—H109120.7C209—C208—C207119.57 (19)
C109—C108—C107120.32 (18)C209—C208—H208120.2
C109—C108—H108119.8C207—C208—H208120.2
C107—C108—H108119.8O201—C207—C208124.66 (18)
O101—C107—C108114.84 (17)O201—C207—C212114.85 (18)
O101—C107—C112124.57 (17)C208—C207—C212120.49 (18)
C108—C107—C112120.59 (18)C211—C212—C207120.10 (19)
C111—C112—C107119.06 (18)C211—C212—H212119.9
C111—C112—H112120.5C207—C212—H212119.9
C107—C112—H112120.5C210—C211—C212118.68 (18)
C110—C111—C112119.49 (18)C210—C211—H211120.7
C110—C111—H111120.3C212—C211—H211120.7
C112—C111—H111120.3C207—O201—C201118.71 (15)
C107—O101—C101118.97 (15)O205—C201—O201111.51 (15)
O105—C101—O101112.63 (16)O205—C201—C202112.49 (16)
O105—C101—C102112.46 (15)O201—C201—C202105.56 (15)
O101—C101—C102105.23 (15)O205—C201—H201109.1
O105—C101—H101108.8O201—C201—H201109.1
O101—C101—H101108.8C202—C201—H201109.1
C102—C101—H101108.8O202—C202—C203109.15 (15)
O102—C102—C103108.21 (15)O202—C202—C201109.41 (15)
O102—C102—C101108.67 (16)C203—C202—C201109.08 (15)
C103—C102—C101109.26 (15)O202—C202—H202109.7
O102—C102—H102110.2C203—C202—H202109.7
C103—C102—H102110.2C201—C202—H202109.7
C101—C102—H102110.2C202—O202—H22106 (2)
C102—O102—H12108 (2)O203—C203—C204109.13 (14)
O103—C103—C104112.48 (15)O203—C203—C202109.29 (15)
O103—C103—C102108.43 (15)C204—C203—C202111.63 (15)
C104—C103—C102109.58 (16)O203—C203—H203108.9
O103—C103—H103108.8C204—C203—H203108.9
C104—C103—H103108.8C202—C203—H203108.9
C102—C103—H103108.8C203—O203—H23109 (2)
C103—O103—H13110 (2)O204—C204—C203110.44 (15)
O104—C104—C103111.05 (16)O204—C204—C205111.02 (15)
O104—C104—C105107.24 (15)C203—C204—C205111.23 (15)
C103—C104—C105108.90 (16)O204—C204—H204108
O104—C104—H104109.9C203—C204—H204108
C103—C104—H104109.9C205—C204—H204108
C105—C104—H104109.9C204—O204—H24110 (2)
C104—O104—H14113 (3)C205—C206—H20A109.5
O105—C105—C106106.61 (16)C205—C206—H20B109.5
O105—C105—C104109.04 (15)H20A—C206—H20B109.5
C106—C105—C104113.64 (17)C205—C206—H20C109.5
O105—C105—H105109.2H20A—C206—H20C109.5
C106—C105—H105109.2H20B—C206—H20C109.5
C104—C105—H105109.2O205—C205—C206106.63 (15)
C105—C106—H10A109.5O205—C205—C204108.41 (14)
C105—C106—H10B109.5C206—C205—C204113.74 (16)
H10A—C106—H10B109.5O205—C205—H205109.3
C105—C106—H10C109.5C206—C205—H205109.3
H10A—C106—H10C109.5C204—C205—H205109.3
H10B—C106—H10C109.5C201—O205—C205113.88 (14)
C101—O105—C105114.15 (14)H1A—O1—H1B109 (3)
O214—N213—O215122.95 (17)
O115—N113—C110—C1110.4 (3)O214—N213—C210—C211165.9 (2)
O114—N113—C110—C111−179.17 (19)O215—N213—C210—C211−14.1 (3)
O115—N113—C110—C109−179.6 (2)O214—N213—C210—C209−14.0 (3)
O114—N113—C110—C1090.8 (3)O215—N213—C210—C209166.02 (19)
C111—C110—C109—C108−0.3 (3)C211—C210—C209—C2081.3 (3)
N113—C110—C109—C108179.77 (18)N213—C210—C209—C208−178.75 (17)
C110—C109—C108—C1070.3 (3)C210—C209—C208—C207−1.0 (3)
C109—C108—C107—O101−179.59 (18)C209—C208—C207—O201−179.57 (18)
C109—C108—C107—C1120.0 (3)C209—C208—C207—C2120.0 (3)
O101—C107—C112—C111179.37 (18)O201—C207—C212—C211−179.71 (17)
C108—C107—C112—C111−0.1 (3)C208—C207—C212—C2110.6 (3)
C109—C110—C111—C1120.1 (3)C209—C210—C211—C212−0.7 (3)
N113—C110—C111—C112−179.95 (18)N213—C210—C211—C212179.43 (17)
C107—C112—C111—C1100.1 (3)C207—C212—C211—C210−0.3 (3)
C108—C107—O101—C101−161.68 (17)C208—C207—O201—C201−7.9 (3)
C112—C107—O101—C10118.8 (3)C212—C207—O201—C201172.50 (17)
C107—O101—C101—O105−69.4 (2)C207—O201—C201—O205−56.3 (2)
C107—O101—C101—C102167.78 (16)C207—O201—C201—C202−178.77 (15)
O105—C101—C102—O10264.6 (2)O205—C201—C202—O20266.1 (2)
O101—C101—C102—O102−172.44 (15)O201—C201—C202—O202−172.04 (14)
O105—C101—C102—C103−53.3 (2)O205—C201—C202—C203−53.2 (2)
O101—C101—C102—C10369.69 (19)O201—C201—C202—C20368.62 (19)
O102—C102—C103—O10359.34 (19)O202—C202—C203—O20351.0 (2)
C101—C102—C103—O103177.50 (14)C201—C202—C203—O203170.50 (15)
O102—C102—C103—C104−63.78 (19)O202—C202—C203—C204−69.81 (19)
C101—C102—C103—C10454.4 (2)C201—C202—C203—C20449.7 (2)
O103—C103—C104—O10462.8 (2)O203—C203—C204—O20462.33 (19)
C102—C103—C104—O104−176.49 (15)C202—C203—C204—O204−176.76 (14)
O103—C103—C104—C105−179.32 (15)O203—C203—C204—C205−173.93 (14)
C102—C103—C104—C105−58.6 (2)C202—C203—C204—C205−53.0 (2)
O104—C104—C105—O105179.73 (15)O204—C204—C205—O205179.33 (14)
C103—C104—C105—O10559.5 (2)C203—C204—C205—O20555.92 (19)
O104—C104—C105—C106−61.5 (2)O204—C204—C205—C206−62.3 (2)
C103—C104—C105—C106178.25 (17)C203—C204—C205—C206174.33 (16)
O101—C101—O105—C105−61.5 (2)O201—C201—O205—C205−57.5 (2)
C102—C101—O105—C10557.2 (2)C202—C201—O205—C20560.9 (2)
C106—C105—O105—C101177.03 (16)C206—C205—O205—C201176.29 (15)
C104—C105—O105—C101−59.9 (2)C204—C205—O205—C201−60.88 (19)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1A···O202i0.86 (3)1.97 (7)2.803 (7)159 (9)
O1—H1B···O102ii0.84 (8)2.06 (1)2.881 (8)162 (7)
O102—H12···O104iii0.84 (5)1.87 (3)2.695 (6)163 (8)
O103—H13···O203iv0.83 (0)2.12 (3)2.934 (2)165 (6)
O104—H14···O203iv0.80 (8)1.89 (5)2.663 (7)158 (5)
O202—H22···O1iv0.88 (0)1.82 (0)2.695 (8)173 (0)
O203—H23···O204v0.83 (7)1.80 (6)2.641 (8)176 (8)
O204—H24···O103vi0.79 (7)1.99 (1)2.776 (5)168 (4)

Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, y−3/2, −z+1; (iii) x, y+1, z; (iv) −x, y+1/2, −z+1; (v) −x, y−1/2, −z+1; (vi) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2086).

References

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