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The title compound [systematic name: 3-hydr­oxy-4,5-bis­(hydroxy­meth­yl)-2-methyl­pyridinium 2,4,6-trinitro­phenolate], C8H12NO3+·C6H2N3O7-, is a complex of picric acid with pyridoxine. The asymmetric part of the unit cell contains one pyridoxinium cation and one picrate anion. The aromatic rings of the picrate anion and the pyridoxinium cation are inclined with a dihedral angle of 83.19 (7)°. An intra­molecular hydrogen bond between OH and a nearby CH2OH group is observed in the cation. The hydro­phobic layers at y = {1 \over 2} are packed between the hydro­philic layers at y = 0.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106018373/dn3016sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106018373/dn3016Isup2.hkl
Contains datablock I

CCDC reference: 616146

Comment top

Vitamin B6, also known as pyridoxine, is one of the B group vitamins and is water-soluble. It is required for both mental and physical health. Pyridoxine is one of the most versatile enzyme cofactors that support amino acid metabolism. It controls the absorption, metabolism and conversion of amino acids into neurotransmitters, antibodies, digestive enzymes, muscles and tissues in the body. Pyridoxal phosphate is a cofactor in the metabolism of amino acids and neurotransmitters and in the breakdown of glycogen. Pyridoxal phosphate can bind to steroid hormone receptors and may have a role in regulating steroid hormone action. Pyridoxal phosphate can be converted to pyridoxamine phosphate, which can also serve as an enzyme cofactor (Leklem, 1990). Pyridoxine has been found to play an essential role in the nervous system and aids in the metabolism of fats, carbohydrates and proteins. Other forms of vitamin B6 include pyridoxal and pyridoxamine.

The crystal structures of pyridoxine (Longo et al., 1982), pyridoxinium chloride (Bacon & Plant, 1980), pyridoxamine monohydrochloride (Longo & Richardson, 1980), copper complexes of neutral pyridoxamine (Franklin & Richardson, 1980), cis-(oxalato-O,O')bis(pyridoxine-N)palladium(II) (Dey et al., 2003), 6-dimethylaminopyridoxine-α4-(tert-butyldimethylsilyl ether) (Culbertson et al., 2003) and aquabis(2-methyl-4,5-bis(hydroxymethyl)pyridinium-3-oxalato-O,O')dioxouranium dichloride (Bonfada et al., 2005) are already known. In the present work, the crystal structure of pyridoxinium picrate, (I), is reported.

The asymmetric part of the unit cell contains one pyridoxinium cation and one picrate anion (Fig. 1). The bond distances and angles are similar to those observed in other vitamin B6 compounds (Bacon & Plant, 1980). The protonation of pyridine N is confirmed by the bond distances and angles, as in other pyridoxine complexes. Generally, in all the structures so far determined, the vitamin B6 exists as a zwitterion in which the phenolic group is deprotonated and the pyridine N is protonated (Longo & Richardson, 1980). In the present structure, both the phenolic group and the pyridine N are protonated, as in pyridoxinium chloride (Bacon & Plant, 1980). In both CH2OH groups, the OH group is symmetric with CH2, as evident from the dihedral angles. Both CH2OH groups are twisted from the plane of the pyridine ring, but the phenolic group is coplanar. The angle between the picrate and pyridoxine rings is 83.19?(7)°. The cations are linked to the picrate anions by an extensive hydrogen-bonding network.

The loss of a proton in the picrate anion is confirmed by the C—C distances near to the phenolic group (C11—C12 and C11—C16). The picrate anion plays a vital role in forming hydrogen bonds with the pyridoxinium residue. The anion forms a strong asymmetric O—H···O hydrogen bond and an N—H···O hydrogen bond with the pyridoxinium residue. Of the three nitro groups, two (N1–O2/O3 and N3–O6/O7) are twisted from the plane of the ring. This twisting property does not depend upon the C—N bond distances (Soriano-Garcia et al., 1978). The torsion angles are shown in Table 1. The picrate anions are stacked nearly parallel to the bc plane, making an angle of 15.86° with the bc plane. N1—H1···O11 and O5—H5···O11/O12 are the intermolecular hydrogen bonds which link pairs of picric acid molecules through O and NO2 groups. In addition to the hydrogen bonds, intramolecular contacts between phenolic O and nitro groups are observed. These are the important features observed in all aromatic picrate complexes.

The pyridine N and atom O5 form bifurcated hydrogen bonds with picrate anions, thus forming an infinite chain running along the a axis (Fig. 2). An intramolecular hydrogen bond between OH and a nearby CH2OH group is observed, with graph-set motif R11(6) (Etter et al., 1990). The pyridoxinium cation forms a closed dimer with an inversely related cation via C—H···O and O—H···O hydrogen bonds. The cation also forms a head-to-tail sequence with inversely related cations through picrate anions via N—H···O and O—H···O hydrogen bonds. The hydrophobic layers at y = 1/2 are packed between the hydrophilic layers at y = 0 (Fig. 3).

Experimental top

The title compound, (I), was crystallized from liquid mixtures [Solutions? In what solvents?] of pyridoxinium chloride with picric acid in the stoichiometric ratio 1:1 at room temperature by the technique of slow evaporation.

Refinement top

All H atoms were placed in geometrically calculated positions and included in the refinement in the riding–model approximation, with O—H = 0.82 Å, C—H = 0.93–0.96 Å and N—H = 0.86 Å, and with Uiso(H) = 1.2–1.5Ueq of the carrier atom.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2003) and Mercury (Version 1.4.1; Macrae et al., 2006); software used to prepare material for publication: SHELXTL/PC.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. An infinite chain connecting two inversely related picrate anions with cations, running along the a axis.
[Figure 3] Fig. 3. A packing diagram for (I), viewed down the b axis. Hydrogen bonds are shown as dashed lines. H atoms which are not involved in hydrogen bonding have been omitted for clarity.
3-hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridinium 2,4,6-trinitrophenolate top
Crystal data top
C8H12NO3+·C6H2N3O7Z = 2
Mr = 398.29F(000) = 412
Triclinic, P1Dx = 1.640 Mg m3
Dm = 1.64 Mg m3
Dm measured by flotation using a mixture of CCl4 and bromoform
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.094 (2) ÅCell parameters from 25 reflections
b = 8.522 (3) Åθ = 9.8–13.6°
c = 12.847 (5) ŵ = 0.14 mm1
α = 87.20 (2)°T = 293 K
β = 85.70 (1)°Nearly cubic block, yellow
γ = 65.92 (2)°0.3 × 0.25 × 0.2 mm
V = 806.6 (5) Å3
Data collection top
Nonius MACH3
diffractometer
2191 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.009
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
ω/2θ scansh = 19
Absorption correction: ψ scan
(North et al., 1968)
k = 910
Tmin = 0.912, Tmax = 0.999l = 1515
3502 measured reflections3 standard reflections every 60 min
2844 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0655P)2 + 0.4805P]
where P = (Fo2 + 2Fc2)/3
2844 reflections(Δ/σ)max < 0.001
256 parametersΔρmax = 0.66 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C8H12NO3+·C6H2N3O7γ = 65.92 (2)°
Mr = 398.29V = 806.6 (5) Å3
Triclinic, P1Z = 2
a = 8.094 (2) ÅMo Kα radiation
b = 8.522 (3) ŵ = 0.14 mm1
c = 12.847 (5) ÅT = 293 K
α = 87.20 (2)°0.3 × 0.25 × 0.2 mm
β = 85.70 (1)°
Data collection top
Nonius MACH3
diffractometer
2191 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.009
Tmin = 0.912, Tmax = 0.9993 standard reflections every 60 min
3502 measured reflections intensity decay: none
2844 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 1.05Δρmax = 0.66 e Å3
2844 reflectionsΔρmin = 0.32 e Å3
256 parameters
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.6717 (3)0.3997 (2)0.79623 (15)0.0379 (5)
H10.74580.41870.75120.045*
C20.7410 (3)0.2717 (3)0.86655 (17)0.0332 (5)
C210.9399 (3)0.1699 (3)0.8642 (2)0.0443 (6)
H21A0.99760.21260.80870.066*0.50
H21B0.96620.05140.85260.066*0.50
H21C0.98450.17980.92960.066*0.50
H21D0.96790.08330.91860.066*0.50
H21E0.99940.24440.87470.066*0.50
H21F0.98100.11600.79770.066*0.50
C30.6181 (3)0.2422 (3)0.93803 (16)0.0325 (5)
O30.6923 (2)0.1113 (2)1.00772 (14)0.0495 (5)
H30.61600.11571.05460.074*
C40.4322 (3)0.3418 (3)0.93571 (16)0.0306 (5)
C50.3703 (3)0.4754 (3)0.86080 (17)0.0331 (5)
C60.4956 (3)0.4993 (3)0.79160 (18)0.0386 (5)
H60.45730.58610.74080.046*
C410.2996 (3)0.3057 (3)1.01079 (18)0.0407 (6)
H41A0.18920.40901.02040.049*
H41B0.26910.21740.98360.049*
O40.3809 (3)0.2499 (3)1.10729 (14)0.0618 (6)
H40.31330.22281.14770.093*
C510.1735 (3)0.5936 (3)0.8535 (2)0.0411 (6)
H51A0.12660.65160.91920.049*
H51B0.16180.68030.79940.049*
O50.0709 (2)0.5007 (2)0.83026 (14)0.0485 (5)
H50.01190.54520.77940.073*
C110.7920 (3)0.6687 (3)0.58805 (17)0.0321 (5)
O110.8381 (2)0.5760 (2)0.66901 (12)0.0417 (4)
C120.7925 (3)0.8386 (3)0.57296 (17)0.0335 (5)
N110.8429 (3)0.9155 (3)0.65702 (15)0.0410 (5)
O120.8313 (3)0.8681 (3)0.74744 (13)0.0564 (5)
O130.9049 (4)1.0227 (3)0.63355 (16)0.0762 (7)
C130.7509 (3)0.9349 (3)0.48230 (17)0.0354 (5)
H130.75441.04270.47740.042*
C140.7039 (3)0.8697 (3)0.39857 (17)0.0344 (5)
N120.6560 (3)0.9713 (3)0.30265 (16)0.0443 (5)
O140.6626 (4)1.1115 (3)0.29815 (16)0.0737 (7)
O150.6133 (3)0.9123 (3)0.22987 (15)0.0674 (6)
C150.7008 (3)0.7087 (3)0.40373 (17)0.0355 (5)
H150.67170.66490.34620.043*
C160.7414 (3)0.6143 (3)0.49516 (17)0.0323 (5)
N130.7326 (3)0.4471 (2)0.49512 (16)0.0398 (5)
O160.7795 (3)0.3653 (2)0.41452 (15)0.0582 (5)
O170.6714 (3)0.3983 (3)0.57398 (15)0.0658 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0395 (11)0.0431 (11)0.0357 (10)0.0226 (9)0.0020 (8)0.0082 (8)
C20.0362 (12)0.0337 (11)0.0331 (11)0.0167 (10)0.0069 (9)0.0005 (9)
C210.0377 (13)0.0462 (14)0.0488 (14)0.0163 (11)0.0042 (11)0.0017 (11)
C30.0392 (13)0.0307 (11)0.0305 (11)0.0166 (10)0.0097 (9)0.0053 (9)
O30.0457 (10)0.0462 (10)0.0497 (10)0.0133 (8)0.0092 (8)0.0240 (8)
C40.0364 (12)0.0335 (11)0.0280 (10)0.0201 (10)0.0056 (9)0.0009 (8)
C50.0387 (12)0.0311 (11)0.0328 (11)0.0167 (10)0.0097 (9)0.0032 (9)
C60.0453 (14)0.0370 (12)0.0359 (12)0.0194 (11)0.0103 (10)0.0135 (10)
C410.0417 (13)0.0497 (14)0.0349 (12)0.0234 (11)0.0054 (10)0.0081 (10)
O40.0558 (12)0.0954 (16)0.0388 (10)0.0379 (11)0.0074 (8)0.0277 (10)
C510.0396 (13)0.0382 (13)0.0441 (13)0.0135 (11)0.0109 (10)0.0043 (10)
O50.0469 (10)0.0559 (11)0.0511 (11)0.0284 (9)0.0217 (8)0.0180 (8)
C110.0286 (11)0.0351 (11)0.0331 (11)0.0142 (9)0.0036 (9)0.0076 (9)
O110.0509 (10)0.0474 (9)0.0363 (9)0.0292 (8)0.0163 (7)0.0174 (7)
C120.0370 (12)0.0358 (12)0.0302 (11)0.0172 (10)0.0050 (9)0.0028 (9)
N110.0521 (12)0.0387 (11)0.0365 (11)0.0224 (10)0.0085 (9)0.0050 (8)
O120.0837 (14)0.0683 (12)0.0325 (9)0.0466 (11)0.0059 (9)0.0036 (8)
O130.131 (2)0.0796 (15)0.0555 (12)0.0798 (16)0.0200 (12)0.0097 (11)
C130.0372 (12)0.0312 (11)0.0375 (12)0.0140 (10)0.0039 (10)0.0052 (9)
C140.0360 (12)0.0337 (12)0.0305 (11)0.0116 (10)0.0050 (9)0.0090 (9)
N120.0501 (12)0.0383 (11)0.0391 (11)0.0124 (9)0.0110 (9)0.0112 (9)
O140.119 (2)0.0486 (12)0.0639 (13)0.0424 (13)0.0376 (13)0.0291 (10)
O150.1050 (17)0.0571 (12)0.0413 (10)0.0308 (12)0.0331 (11)0.0130 (9)
C150.0370 (12)0.0378 (12)0.0313 (11)0.0146 (10)0.0051 (9)0.0007 (9)
C160.0337 (11)0.0296 (11)0.0349 (11)0.0143 (9)0.0035 (9)0.0037 (9)
N130.0458 (12)0.0353 (10)0.0414 (11)0.0193 (9)0.0094 (9)0.0054 (9)
O160.0796 (14)0.0472 (11)0.0541 (11)0.0311 (10)0.0041 (10)0.0101 (9)
O170.1070 (18)0.0627 (13)0.0502 (11)0.0583 (13)0.0075 (11)0.0123 (9)
Geometric parameters (Å, º) top
N1—C61.333 (3)C51—O51.415 (3)
N1—C21.342 (3)C51—H51A0.9700
N1—H10.8600C51—H51B0.9700
C2—C31.394 (3)O5—H50.8200
C2—C211.483 (3)C11—O111.258 (3)
C21—H21A0.9600C11—C161.445 (3)
C21—H21B0.9600C11—C121.453 (3)
C21—H21C0.9600C12—C131.372 (3)
C21—H21D0.9600C12—N111.455 (3)
C21—H21E0.9600N11—O121.221 (3)
C21—H21F0.9600N11—O131.226 (3)
C3—O31.357 (3)C13—C141.379 (3)
C3—C41.396 (3)C13—H130.9300
O3—H30.8200C14—C151.381 (3)
C4—C51.405 (3)C14—N121.453 (3)
C4—C411.503 (3)N12—O141.216 (3)
C5—C61.370 (3)N12—O151.218 (3)
C5—C511.505 (3)C15—C161.373 (3)
C6—H60.9300C15—H150.9300
C41—O41.416 (3)C16—N131.455 (3)
C41—H41A0.9700N13—O171.223 (3)
C41—H41B0.9700N13—O161.224 (3)
O4—H40.8200
C6—N1—C2124.4 (2)O4—C41—H41A110.0
C6—N1—H1117.8C4—C41—H41A110.0
C2—N1—H1117.8O4—C41—H41B110.0
N1—C2—C3116.7 (2)C4—C41—H41B110.0
N1—C2—C21119.5 (2)H41A—C41—H41B108.4
C3—C2—C21123.8 (2)C41—O4—H4109.5
C2—C21—H21A109.5O5—C51—C5110.83 (19)
C2—C21—H21B109.5O5—C51—H51A109.5
H21A—C21—H21B109.5C5—C51—H51A109.5
C2—C21—H21C109.5O5—C51—H51B109.5
H21A—C21—H21C109.5C5—C51—H51B109.5
H21B—C21—H21C109.5H51A—C51—H51B108.1
C2—C21—H21D109.5C51—O5—H5109.5
H21A—C21—H21D141.1O11—C11—C16123.7 (2)
H21B—C21—H21D56.3O11—C11—C12125.0 (2)
H21C—C21—H21D56.3C16—C11—C12111.2 (2)
C2—C21—H21E109.5C13—C12—C11124.5 (2)
H21A—C21—H21E56.3C13—C12—N11115.7 (2)
H21B—C21—H21E141.1C11—C12—N11119.73 (19)
H21C—C21—H21E56.3O12—N11—O13121.4 (2)
H21D—C21—H21E109.5O12—N11—C12120.55 (19)
C2—C21—H21F109.5O13—N11—C12117.9 (2)
H21A—C21—H21F56.3C12—C13—C14119.2 (2)
H21B—C21—H21F56.3C12—C13—H13120.4
H21C—C21—H21F141.1C14—C13—H13120.4
H21D—C21—H21F109.5C13—C14—C15121.3 (2)
H21E—C21—H21F109.5C13—C14—N12119.9 (2)
O3—C3—C2115.3 (2)C15—C14—N12118.8 (2)
O3—C3—C4123.6 (2)O14—N12—O15122.7 (2)
C2—C3—C4121.07 (19)O14—N12—C14118.3 (2)
C3—O3—H3109.5O15—N12—C14119.0 (2)
C3—C4—C5118.8 (2)C16—C15—C14118.9 (2)
C3—C4—C41120.85 (19)C16—C15—H15120.6
C5—C4—C41120.3 (2)C14—C15—H15120.6
C6—C5—C4118.2 (2)C15—C16—C11125.0 (2)
C6—C5—C51118.6 (2)C15—C16—N13115.7 (2)
C4—C5—C51123.1 (2)C11—C16—N13119.34 (19)
N1—C6—C5120.8 (2)O17—N13—O16123.0 (2)
N1—C6—H6119.6O17—N13—C16118.6 (2)
C5—C6—H6119.6O16—N13—C16118.3 (2)
O4—C41—C4108.31 (19)
C6—N1—C2—C30.8 (3)C13—C12—N11—O12158.8 (2)
C6—N1—C2—C21179.6 (2)C11—C12—N11—O1222.2 (4)
N1—C2—C3—O3179.7 (2)C13—C12—N11—O1324.7 (3)
C21—C2—C3—O30.2 (3)C11—C12—N11—O13154.3 (2)
N1—C2—C3—C40.1 (3)C11—C12—C13—C140.4 (4)
C21—C2—C3—C4179.6 (2)N11—C12—C13—C14179.4 (2)
O3—C3—C4—C5179.3 (2)C12—C13—C14—C151.1 (4)
C2—C3—C4—C51.0 (3)C12—C13—C14—N12178.8 (2)
O3—C3—C4—C411.7 (3)C15—C14—N12—O14178.4 (3)
C2—C3—C4—C41178.0 (2)C13—C14—N12—O141.7 (4)
C3—C4—C5—C61.3 (3)C15—C14—N12—O150.5 (4)
C41—C4—C5—C6177.7 (2)C13—C14—N12—O15179.4 (2)
C3—C4—C5—C51178.1 (2)C13—C14—C15—C161.6 (4)
C41—C4—C5—C512.8 (3)N12—C14—C15—C16178.3 (2)
C2—N1—C6—C50.5 (4)C14—C15—C16—C111.4 (4)
C4—C5—C6—N10.6 (3)C14—C15—C16—N13179.0 (2)
C51—C5—C6—N1178.9 (2)O11—C11—C16—C15176.0 (2)
C3—C4—C41—O435.1 (3)C12—C11—C16—C150.7 (3)
C5—C4—C41—O4145.9 (2)O11—C11—C16—N133.5 (4)
C6—C5—C51—O5117.9 (2)C12—C11—C16—N13179.8 (2)
C4—C5—C51—O562.6 (3)C15—C16—N13—O17141.4 (2)
O11—C11—C12—C13176.5 (2)C11—C16—N13—O1739.1 (3)
C16—C11—C12—C130.2 (3)C15—C16—N13—O1635.4 (3)
O11—C11—C12—N112.4 (4)C11—C16—N13—O16144.1 (2)
C16—C11—C12—N11179.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O110.862.012.797 (2)152
O3—H3···O40.821.872.572 (3)143
O4—H4···O12i0.822.052.862 (3)174
O5—H5···O11ii0.822.012.779 (2)157
C21—H21B···O12iii0.962.703.472 (3)138
C21—H21F···O13iii0.962.493.348 (3)148
C6—H6···O14iv0.932.403.217 (3)147
Symmetry codes: (i) x+1, y+1, z+2; (ii) x1, y, z; (iii) x, y1, z; (iv) x+1, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC8H12NO3+·C6H2N3O7
Mr398.29
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.094 (2), 8.522 (3), 12.847 (5)
α, β, γ (°)87.20 (2), 85.70 (1), 65.92 (2)
V3)806.6 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.14
Crystal size (mm)0.3 × 0.25 × 0.2
Data collection
DiffractometerNonius MACH3
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.912, 0.999
No. of measured, independent and
observed [I > 2σ(I)] reflections
3502, 2844, 2191
Rint0.009
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.130, 1.05
No. of reflections2844
No. of parameters256
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.66, 0.32

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXTL/PC (Bruker, 2000), SHELXTL/PC, ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2003) and Mercury (Version 1.4.1; Macrae et al., 2006).

Selected geometric parameters (Å, º) top
N1—C61.333 (3)C11—O111.258 (3)
N1—C21.342 (3)
C6—N1—C2124.4 (2)O11—C11—C12125.0 (2)
O11—C11—C16123.7 (2)C16—C11—C12111.2 (2)
N1—C2—C3—O3179.7 (2)C4—C5—C51—O562.6 (3)
C21—C2—C3—O30.2 (3)C11—C12—N11—O1222.2 (4)
O3—C3—C4—C5179.3 (2)C13—C12—N11—O1324.7 (3)
O3—C3—C4—C411.7 (3)C13—C14—N12—O141.7 (4)
C3—C4—C41—O435.1 (3)C15—C14—N12—O150.5 (4)
C5—C4—C41—O4145.9 (2)C11—C16—N13—O1739.1 (3)
C6—C5—C51—O5117.9 (2)C15—C16—N13—O1635.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O110.862.012.797 (2)152.2
O3—H3···O40.821.872.572 (3)143.1
O4—H4···O12i0.822.052.862 (3)173.8
O5—H5···O11ii0.822.012.779 (2)156.9
C21—H21B···O12iii0.962.703.472 (3)138.1
C21—H21F···O13iii0.962.493.348 (3)148.2
C6—H6···O14iv0.932.403.217 (3)147.2
Symmetry codes: (i) x+1, y+1, z+2; (ii) x1, y, z; (iii) x, y1, z; (iv) x+1, y+2, z+1.
 

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