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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 68| Part 4| April 2012| Pages o1054-o1055
doi:10.1107/S160053681200935X

(R)-Doxylaminium (R,R)-tartrate

A.S. Dayananda,a Grzegorz Dutkiewicz,b H. S. Yathirajana and Maciej Kubickib*

aDepartment of Studies in Chemistry, University of Mysore, Mysore 570 006, India, and bDepartment of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland
*Correspondence e-mail: mkubicki@amu.edu.pl

(Received 30 January 2012; accepted 2 March 2012; online 14 March 2012)

In the title compound (systematic name: (R)-dimeth­yl{2-[1-phenyl-1-(pyridin-2-yl)eth­oxy]eth­yl}aza­nium (R,R)-3-carb­oxy-2,3-dihy­droxy­propano­ate), C17H23N2O+·C4H5O6−, the doxylaminium cation is protonated at the N atom. The tartrate monoanions are linked by short, almost linear O—H⋯O hydrogen bonds into chains extended along [100]. These chains are inter­linked by anion–pyridine O—H⋯N hydrogen bonds into a two-dimensional grid structure. WeakC—H⋯O inter­actions also play a role in the crystal packing. An intra­molecular hy­droxy–carboxyl­ate O—H⋯O hydrogen bond influences the conformation of the anion: the hydrogen-bonded fragment is almost planar, the maximum deviation from the mean plane being 0.059 (14) Å. In the cation, the aromatic rings are almost perpendicular [dihedral angle = 84.94 (8)°] and the conformation of the O—C—C—N chain is gauche(−), the dihedral angle is −76.6 (2)°. The absolute configuration was assigned on the basis of known chirality of the parent compound.

Related literature

For related strucures, see: Braitenbach & Parvez (2001[Braitenbach, K. & Parvez, M. (2001). Acta Cryst. C57, 262-263.]); Parvez & Sabir (1998[Parvez, M. & Sabir, A. P. (1998). Acta Cryst. C54, 933-935.]); Parvez et al. (2001[Parvez, M., Dalrymple, S. & Cote, A. (2001). Acta Cryst. E57, o163-o165.]). For general literature on doxyl­amine, see, for example: Casy (1991[Casy, A. F. (1991). In Histamine and Histamine Antagonists, edited by B. Uvnas, pp. 858-862. Berlin, Heidelberg: Springer-Verlag.]); Eccles et al. (1995[Eccles, R., Van Cauwenberge, P., Tetzloff, W. & Borum, P. (1995). J. Pharm. Pharmacol. 47, 990-993.]). For graph-set motifs, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data

  • C17H23N2O+·C4H5O6−

  • Mr = 420.45

  • Monoclinic, P 21

  • a = 7.4419 (4) Å

  • b = 18.4394 (8) Å

  • c = 8.3517 (4) Å

  • β = 108.301 (5)°

  • V = 1088.09 (9) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 295 K

  • 0.35 × 0.2 × 0.15 mm
Data collection

  • Agilent Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.991, Tmax = 1.000

  • 4562 measured reflections

  • 3539 independent reflections

  • 3228 reflections with I > 2σ(I)

  • Rint = 0.011
Refinement

  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.079

  • S = 1.06

  • 3539 reflections

  • 290 parameters

  • 1 restraint

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

  • Δρmax = 0.11 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C42—H42A⋯O3A 0.97 2.52 3.391 (3) 149
C43—H43B⋯O41Ai 0.97 2.27 3.217 (3) 165
N44—H44⋯O12A 0.86 (3) 2.23 (3) 2.942 (2) 140 (2)
O2A—H2A1⋯N32ii 0.89 (4) 1.92 (4) 2.804 (2) 171 (3)
O3A—H3A1⋯O41A 0.81 (3) 2.08 (3) 2.613 (2) 123 (3)
O42A—H42⋯O12Aiii 1.12 (3) 1.33 (3) 2.4475 (18) 178 (3)
Symmetry codes: (i) x-1, y, z; (ii) [-x+1, y-{\script{1\over 2}}, -z+1]; (iii) x+1, y, z.

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: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681200935X/nr2021sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681200935X/nr2021Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681200935X/nr2021Isup3.cml

checkCIF report


Comment top

Doxylamine (dimethyl-[2-(1-phenyl-1-pyridin-2-yl-ethoxy)-ethyl]-amine) is a chiral tertiary aminoalkyl ether, which exhibits an antihistaminic action on the H1 receptor site (e.g. Casy, 1991). It is used as a short-term sedative, and - in combination with other drugs - as a night-time cold and allergy relief drug (Eccles et al., 1995).

There are not many crystal structures of related compounds in the Cambridge Crystallographic Database (Allen, 2002), and these are exclusively salts: monoprotonated doxylaminium hydrogen succinate (Parvez et al., 2001), and diprotonated doxylaminium tetrachlorocuprate(II) (Braitenbach & Parvez, 2001), and isostructural tetrachlorozincate(II) and tetrachlorocobaltate(II) (Parvez & Sabir, 1998). In view of the importance of doxylamine, we have determined the crystal and molecular structure of the title salt, (1, Scheme 1), (R)-doxylaminium (R,R)-tartarate. The absolute configuration was assigned on the basis of known chirality of the parent compound.

In 1 doxylamine is monoprotonated at N44, thus giving a quaternary ammonium cation (Fig. 1). This 'additional' hydrogen atom was found in the difference Fourier map and successfully refined. The aromatic rings in the cation are almost perpendicular, the dihedral angle between the least-squares planes of phenyl (planar within 0.0064 (16) Å) and pyridine (0.0056 (16) Å) rings is 84.94 (8)°. The conformation along C—O—C—C—N chain is tg-, the appropriate torsion angles are -164.77 (18)° and -76.6 (2)°. Similar conformation has been observed in previously reported doxylamine salts, despite the presence of intra-cationic hydrogen bonds in the di-cations (Parvez & Sabir, 1998, Braitenbach & Parvez, 2001).

In the anion the carbon chain is in an extended conformation (C—C—C—C torsion angle is -178.33 (16)°), and the overall conformation of the anion might be described by the dihedral angle betwen the two approximately planar 'halves': C1A, O11A, O12A, C2A and C3A, C4A, O41A, O42A, which is 43.45 (8) °. It might be noted that due to the intramolecular O3A—H···O41A hydrogen bond (cf. Table 1), the O3A oxygen atom is almost coplanar with the CCOO plane (0.033 (4) Å), while O2A is significantly deviated from similar plane, by -0.420 (3) Å.

In the crystal very short and almost linear O—H···O (x + 1,y,z) hydrogen bonds (O—H 1.12 (3) Å, H···O 1.33 (3) Å, O···O 2.4475 (18) Å, O—H···O 178 (3) °) connect the anions into infinite chains along x direction. As frequent happens for this kind of short bonds, the O—H bond is elongated, while H···O contact is quite short, which might suggest the covalent component in both of them. The anionic chains are connexted with the cations by means of N—H···O and O—H···N hydrogen bonds creating the rings (Fig. 2) which can be described as R65(36) (Etter et al., 1990, Bernstein et al., 1995). Repetition of these rings produces the chessboard-like pattern of anions and cations in the crystal structure (Fig. 3). Some secondary C—H···O interactions are also playing a role in the crystal packing.

Related literature top

For related strucures, see: Braitenbach & Parvez (2001); Parvez & Sabir (1998); Parvez et al. (2001). For general literature on doxylamine, see, for example: Casy (1991); Eccles et al. (1995). For graph-set motifs, see: Etter et al. (1990); Bernstein et al. (1995). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

The title compound was obtained as a gift sample from R. L. Fine Chem., Bengaluru, India. The compound was recrystallized from methanol by slow evaporation (m.p: 388 K).

Refinement top

Hydrogen atoms attached to O and N atoms were found in difference Fourier maps and isotropically refined, all other H atoms were put in the idealized positions, and refined as riding model. Their isotropic thermal parameters were set at 1.2 (1.5 for methyl groups) times Ueq's of appropriate carrier atoms. The Friedel pairs were not merged, however their coverage is relatively low, of ca 50%.

Structure description top

Doxylamine (dimethyl-[2-(1-phenyl-1-pyridin-2-yl-ethoxy)-ethyl]-amine) is a chiral tertiary aminoalkyl ether, which exhibits an antihistaminic action on the H1 receptor site (e.g. Casy, 1991). It is used as a short-term sedative, and - in combination with other drugs - as a night-time cold and allergy relief drug (Eccles et al., 1995).

There are not many crystal structures of related compounds in the Cambridge Crystallographic Database (Allen, 2002), and these are exclusively salts: monoprotonated doxylaminium hydrogen succinate (Parvez et al., 2001), and diprotonated doxylaminium tetrachlorocuprate(II) (Braitenbach & Parvez, 2001), and isostructural tetrachlorozincate(II) and tetrachlorocobaltate(II) (Parvez & Sabir, 1998). In view of the importance of doxylamine, we have determined the crystal and molecular structure of the title salt, (1, Scheme 1), (R)-doxylaminium (R,R)-tartarate. The absolute configuration was assigned on the basis of known chirality of the parent compound.

In 1 doxylamine is monoprotonated at N44, thus giving a quaternary ammonium cation (Fig. 1). This 'additional' hydrogen atom was found in the difference Fourier map and successfully refined. The aromatic rings in the cation are almost perpendicular, the dihedral angle between the least-squares planes of phenyl (planar within 0.0064 (16) Å) and pyridine (0.0056 (16) Å) rings is 84.94 (8)°. The conformation along C—O—C—C—N chain is tg-, the appropriate torsion angles are -164.77 (18)° and -76.6 (2)°. Similar conformation has been observed in previously reported doxylamine salts, despite the presence of intra-cationic hydrogen bonds in the di-cations (Parvez & Sabir, 1998, Braitenbach & Parvez, 2001).

In the anion the carbon chain is in an extended conformation (C—C—C—C torsion angle is -178.33 (16)°), and the overall conformation of the anion might be described by the dihedral angle betwen the two approximately planar 'halves': C1A, O11A, O12A, C2A and C3A, C4A, O41A, O42A, which is 43.45 (8) °. It might be noted that due to the intramolecular O3A—H···O41A hydrogen bond (cf. Table 1), the O3A oxygen atom is almost coplanar with the CCOO plane (0.033 (4) Å), while O2A is significantly deviated from similar plane, by -0.420 (3) Å.

In the crystal very short and almost linear O—H···O (x + 1,y,z) hydrogen bonds (O—H 1.12 (3) Å, H···O 1.33 (3) Å, O···O 2.4475 (18) Å, O—H···O 178 (3) °) connect the anions into infinite chains along x direction. As frequent happens for this kind of short bonds, the O—H bond is elongated, while H···O contact is quite short, which might suggest the covalent component in both of them. The anionic chains are connexted with the cations by means of N—H···O and O—H···N hydrogen bonds creating the rings (Fig. 2) which can be described as R65(36) (Etter et al., 1990, Bernstein et al., 1995). Repetition of these rings produces the chessboard-like pattern of anions and cations in the crystal structure (Fig. 3). Some secondary C—H···O interactions are also playing a role in the crystal packing.

For related strucures, see: Braitenbach & Parvez (2001); Parvez & Sabir (1998); Parvez et al. (2001). For general literature on doxylamine, see, for example: Casy (1991); Eccles et al. (1995). For graph-set motifs, see: Etter et al. (1990); Bernstein et al. (1995). For a description of the Cambridge Structural Database, see: Allen (2002).

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: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Anisotropic ellipsoid representation of the ionic components of the salt 1, together with atom labelling scheme. The ellipsoids are drawn at 50% probability level, hydrogen atoms are depicted as spheres with arbitrary radii. Intramolecular hydrogen bond is shown as dashed line.
[Figure 2] Fig. 2. The hydrogen-bonded ring of cations and anions. Hydrogen bonds are drawn as dashed lines, symmetry codes: (i) x,y,z; (ii) 1 - x,1/2 + y,1 - z; (iii) -1 + x,y,z; (iv) -x,1/2 + y,1 - z.
[Figure 3] Fig. 3. The crystal packing as seen approximately along c-direction, hydrogen bonds, including weak C—H···O interactions listed in table 1) are drawn as dashed lines.
(R)-dimethyl{2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl}azanium (R,R)-3-carboxy-2,3-dihydroxypropanoate top
Crystal data top
C17H23N2O+·C4H5O6−F(000) = 448
Mr = 420.45Dx = 1.283 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.7107 Å
a = 7.4419 (4) ÅCell parameters from 1885 reflections
b = 18.4394 (8) Åθ = 2.9–27.8°
c = 8.3517 (4) ŵ = 0.10 mm−1
β = 108.301 (5)°T = 295 K
V = 1088.09 (9) Å3Block, colourless
Z = 20.35 × 0.2 × 0.15 mm
Data collection top
Agilent Xcalibur Eos
diffractometer		3539 independent reflections
Radiation source: Enhance (Mo) X-ray Source3228 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
Detector resolution: 16.1544 pixels mm-1θmax = 27.9°, θmin = 2.9°
ω scanh = −5→9
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)		k = −23→19
Tmin = 0.991, Tmax = 1.000l = −10→10
4562 measured reflections
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0316P)2 + 0.1652P]
where P = (Fo2 + 2Fc2)/3
3539 reflections(Δ/σ)max = 0.001
290 parametersΔρmax = 0.11 e Å−3
1 restraintΔρmin = −0.16 e Å−3
Crystal data top
C17H23N2O+·C4H5O6−V = 1088.09 (9) Å3
Mr = 420.45Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.4419 (4) ŵ = 0.10 mm−1
b = 18.4394 (8) ÅT = 295 K
c = 8.3517 (4) Å0.35 × 0.2 × 0.15 mm
β = 108.301 (5)°
Data collection top
Agilent Xcalibur Eos
diffractometer		3539 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)		3228 reflections with I > 2σ(I)
Tmin = 0.991, Tmax = 1.000Rint = 0.011
4562 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0351 restraint
wR(F2) = 0.079H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.11 e Å−3
3539 reflectionsΔρmin = −0.16 e Å−3
290 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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*/Ueq
C10.4272 (3)0.67447 (11)0.6599 (2)0.0349 (5)
C110.3002 (4)0.71964 (15)0.7339 (3)0.0537 (6)
H11A0.17780.72510.65110.081*
H11B0.35590.76660.76540.081*
H11C0.28700.69560.83160.081*
C210.4472 (3)0.70427 (11)0.4958 (3)0.0372 (5)
C220.5716 (4)0.67112 (15)0.4264 (3)0.0524 (6)
H220.64170.63130.47990.063*
C230.5930 (5)0.69689 (19)0.2769 (4)0.0790 (10)
H230.67770.67440.23130.095*
C240.4894 (6)0.7554 (2)0.1966 (4)0.0884 (13)
H240.50450.77270.09700.106*
C250.3652 (6)0.78785 (17)0.2625 (4)0.0791 (11)
H250.29450.82730.20750.095*
C260.3427 (4)0.76266 (14)0.4116 (3)0.0562 (7)
H260.25650.78520.45530.067*
C310.6242 (3)0.66822 (12)0.7900 (2)0.0345 (4)
N320.7191 (3)0.73082 (10)0.8328 (2)0.0462 (5)
C330.8949 (4)0.72791 (14)0.9414 (3)0.0574 (7)
H330.96160.77120.97010.069*
C340.9824 (3)0.66531 (15)1.0129 (3)0.0504 (6)
H341.10490.66591.08800.061*
C350.8848 (4)0.60232 (14)0.9705 (3)0.0536 (7)
H350.93940.55871.01710.064*
C360.7034 (3)0.60348 (13)0.8576 (3)0.0477 (6)
H360.63540.56060.82770.057*
O410.3570 (2)0.60073 (8)0.63556 (17)0.0390 (4)
C420.1862 (3)0.58833 (13)0.5017 (3)0.0426 (5)
H42A0.21100.59020.39450.051*
H42B0.09490.62580.50190.051*
C430.1071 (3)0.51528 (13)0.5234 (3)0.0464 (6)
H43A0.11310.51000.64050.056*
H43B−0.02530.51410.45590.056*
N440.2040 (3)0.45177 (11)0.4760 (2)0.0503 (5)
H440.193 (4)0.4545 (15)0.371 (3)0.057 (7)*
C450.1053 (6)0.38380 (16)0.4956 (4)0.0868 (11)
H45A0.12100.37590.61280.130*
H45B0.15820.34370.45240.130*
H45C−0.02700.38790.43410.130*
C460.4095 (4)0.44705 (16)0.5709 (3)0.0659 (8)
H46A0.42650.44360.68940.099*
H46B0.47250.48960.54930.099*
H46C0.46210.40490.53510.099*
C1A0.0805 (3)0.41864 (11)0.0025 (2)0.0315 (4)
O11A−0.0017 (2)0.42724 (10)−0.14690 (18)0.0513 (4)
O12A0.00315 (19)0.41842 (9)0.12021 (18)0.0435 (4)
C2A0.2953 (3)0.40945 (11)0.0626 (2)0.0304 (4)
H2A0.33070.3787−0.01840.036*
O2A0.3691 (2)0.37835 (9)0.22459 (18)0.0396 (4)
H2A10.344 (5)0.331 (2)0.219 (4)0.095 (12)*
C3A0.3858 (3)0.48319 (11)0.0658 (3)0.0335 (4)
H3A0.34180.5043−0.04760.040*
O3A0.3330 (2)0.52934 (9)0.1788 (2)0.0472 (4)
H3A10.431 (4)0.5477 (17)0.236 (4)0.070 (10)*
C4A0.5998 (3)0.47547 (12)0.1202 (3)0.0360 (5)
O41A0.6965 (2)0.50948 (10)0.2428 (2)0.0549 (5)
O42A0.6590 (2)0.43365 (9)0.0257 (2)0.0470 (4)
H420.816 (5)0.4273 (19)0.067 (4)0.095 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0333 (10)0.0350 (12)0.0343 (10)−0.0003 (10)0.0076 (8)−0.0030 (9)
C110.0449 (13)0.0630 (17)0.0533 (14)0.0032 (13)0.0154 (11)−0.0132 (12)
C210.0427 (12)0.0327 (11)0.0315 (10)−0.0088 (10)0.0047 (9)−0.0027 (8)
C220.0659 (16)0.0510 (14)0.0456 (13)−0.0069 (14)0.0252 (12)−0.0047 (11)
C230.110 (3)0.082 (2)0.0596 (18)−0.041 (2)0.0468 (19)−0.0242 (17)
C240.135 (3)0.084 (3)0.0394 (15)−0.070 (2)0.0173 (19)−0.0019 (16)
C250.104 (3)0.0553 (19)0.0509 (17)−0.0315 (19)−0.0144 (17)0.0186 (14)
C260.0590 (16)0.0426 (14)0.0527 (14)−0.0067 (13)−0.0030 (12)0.0058 (11)
C310.0364 (11)0.0334 (11)0.0343 (10)−0.0040 (10)0.0119 (8)−0.0004 (9)
N320.0458 (11)0.0314 (10)0.0516 (11)−0.0025 (9)0.0012 (9)−0.0018 (8)
C330.0480 (14)0.0370 (13)0.0696 (17)−0.0080 (12)−0.0069 (13)−0.0025 (12)
C340.0364 (12)0.0471 (14)0.0565 (14)−0.0046 (12)−0.0016 (10)0.0051 (11)
C350.0496 (14)0.0397 (14)0.0600 (15)0.0014 (12)0.0007 (12)0.0134 (11)
C360.0441 (13)0.0355 (13)0.0531 (13)−0.0067 (11)0.0003 (11)0.0055 (10)
O410.0360 (8)0.0380 (9)0.0358 (7)−0.0070 (7)0.0007 (6)0.0027 (6)
C420.0364 (12)0.0467 (13)0.0384 (11)−0.0038 (11)0.0026 (9)−0.0004 (10)
C430.0421 (13)0.0539 (15)0.0386 (12)−0.0148 (12)0.0060 (10)−0.0045 (11)
N440.0770 (15)0.0429 (11)0.0271 (10)−0.0149 (11)0.0106 (10)−0.0013 (8)
C450.159 (3)0.0560 (17)0.0523 (16)−0.046 (2)0.043 (2)−0.0080 (13)
C460.082 (2)0.0551 (16)0.0463 (15)0.0186 (15)−0.0007 (14)−0.0058 (12)
C1A0.0257 (9)0.0330 (11)0.0360 (10)−0.0023 (9)0.0100 (8)−0.0020 (9)
O11A0.0340 (7)0.0819 (13)0.0354 (8)0.0022 (8)0.0070 (7)0.0005 (8)
O12A0.0272 (7)0.0677 (11)0.0392 (8)0.0042 (7)0.0155 (6)0.0038 (8)
C2A0.0249 (9)0.0335 (11)0.0330 (10)0.0038 (9)0.0098 (8)−0.0039 (8)
O2A0.0344 (8)0.0369 (9)0.0412 (8)0.0017 (7)0.0029 (6)0.0025 (7)
C3A0.0263 (10)0.0377 (11)0.0361 (10)0.0010 (9)0.0093 (8)−0.0033 (9)
O3A0.0347 (9)0.0432 (10)0.0643 (11)0.0004 (8)0.0161 (8)−0.0182 (8)
C4A0.0256 (10)0.0416 (12)0.0420 (11)−0.0048 (10)0.0125 (9)0.0004 (10)
O41A0.0317 (8)0.0688 (12)0.0575 (10)−0.0053 (8)0.0042 (7)−0.0198 (9)
O42A0.0244 (7)0.0647 (11)0.0551 (9)−0.0016 (7)0.0172 (7)−0.0156 (8)
Geometric parameters (Å, º) top
C1—O411.448 (2)C42—C431.503 (3)
C1—C211.526 (3)C42—H42A0.9700
C1—C111.528 (3)C42—H42B0.9700
C1—C311.531 (3)C43—N441.492 (3)
C11—H11A0.9600C43—H43A0.9700
C11—H11B0.9600C43—H43B0.9700
C11—H11C0.9600N44—C451.487 (3)
C21—C221.380 (3)N44—C461.488 (3)
C21—C261.384 (3)N44—H440.86 (3)
C22—C231.390 (4)C45—H45A0.9600
C22—H220.9300C45—H45B0.9600
C23—C241.372 (5)C45—H45C0.9600
C23—H230.9300C46—H46A0.9600
C24—C251.356 (5)C46—H46B0.9600
C24—H240.9300C46—H46C0.9600
C25—C261.387 (4)C1A—O11A1.216 (2)
C25—H250.9300C1A—O12A1.285 (2)
C26—H260.9300C1A—C2A1.527 (3)
C31—N321.342 (3)C2A—O2A1.412 (2)
C31—C361.372 (3)C2A—C3A1.514 (3)
N32—C331.339 (3)C2A—H2A0.9800
C33—C341.367 (4)O2A—H2A10.89 (4)
C33—H330.9300C3A—O3A1.415 (3)
C34—C351.357 (4)C3A—C4A1.519 (3)
C34—H340.9300C3A—H3A0.9800
C35—C361.383 (3)O3A—H3A10.81 (3)
C35—H350.9300C4A—O41A1.223 (2)
C36—H360.9300C4A—O42A1.277 (2)
O41—C421.423 (2)O42A—H421.12 (3)
O41—C1—C21110.18 (16)C43—C42—H42A109.7
O41—C1—C11109.08 (18)O41—C42—H42B109.7
C21—C1—C11114.45 (19)C43—C42—H42B109.7
O41—C1—C31104.58 (16)H42A—C42—H42B108.2
C21—C1—C31108.82 (17)N44—C43—C42115.6 (2)
C11—C1—C31109.26 (17)N44—C43—H43A108.4
C1—C11—H11A109.5C42—C43—H43A108.4
C1—C11—H11B109.5N44—C43—H43B108.4
H11A—C11—H11B109.5C42—C43—H43B108.4
C1—C11—H11C109.5H43A—C43—H43B107.4
H11A—C11—H11C109.5C45—N44—C46110.7 (3)
H11B—C11—H11C109.5C45—N44—C43109.6 (2)
C22—C21—C26118.4 (2)C46—N44—C43113.97 (18)
C22—C21—C1119.0 (2)C45—N44—H44105.8 (18)
C26—C21—C1122.6 (2)C46—N44—H44107.3 (17)
C21—C22—C23120.4 (3)C43—N44—H44109.1 (18)
C21—C22—H22119.8N44—C45—H45A109.5
C23—C22—H22119.8N44—C45—H45B109.5
C24—C23—C22120.2 (3)H45A—C45—H45B109.5
C24—C23—H23119.9N44—C45—H45C109.5
C22—C23—H23119.9H45A—C45—H45C109.5
C25—C24—C23119.9 (3)H45B—C45—H45C109.5
C25—C24—H24120.0N44—C46—H46A109.5
C23—C24—H24120.0N44—C46—H46B109.5
C24—C25—C26120.4 (3)H46A—C46—H46B109.5
C24—C25—H25119.8N44—C46—H46C109.5
C26—C25—H25119.8H46A—C46—H46C109.5
C21—C26—C25120.6 (3)H46B—C46—H46C109.5
C21—C26—H26119.7O11A—C1A—O12A125.72 (18)
C25—C26—H26119.7O11A—C1A—C2A119.27 (17)
N32—C31—C36121.09 (19)O12A—C1A—C2A114.98 (16)
N32—C31—C1115.55 (18)O2A—C2A—C3A108.10 (16)
C36—C31—C1123.34 (19)O2A—C2A—C1A114.32 (16)
C33—N32—C31117.84 (19)C3A—C2A—C1A108.68 (16)
N32—C33—C34124.1 (2)O2A—C2A—H2A108.5
N32—C33—H33118.0C3A—C2A—H2A108.5
C34—C33—H33118.0C1A—C2A—H2A108.5
C35—C34—C33117.8 (2)C2A—O2A—H2A1110 (2)
C35—C34—H34121.1O3A—C3A—C2A109.67 (17)
C33—C34—H34121.1O3A—C3A—C4A109.98 (16)
C34—C35—C36119.5 (2)C2A—C3A—C4A109.87 (17)
C34—C35—H35120.2O3A—C3A—H3A109.1
C36—C35—H35120.2C2A—C3A—H3A109.1
C31—C36—C35119.7 (2)C4A—C3A—H3A109.1
C31—C36—H36120.1C3A—O3A—H3A1105 (2)
C35—C36—H36120.1O41A—C4A—O42A126.91 (19)
C42—O41—C1117.05 (15)O41A—C4A—C3A119.19 (19)
O41—C42—C43109.65 (18)O42A—C4A—C3A113.88 (17)
O41—C42—H42A109.7C4A—O42A—H42113.8 (17)
O41—C1—C21—C22−62.2 (3)C33—C34—C35—C360.4 (4)
C11—C1—C21—C22174.4 (2)N32—C31—C36—C35−0.7 (4)
C31—C1—C21—C2251.9 (3)C1—C31—C36—C35177.9 (2)
O41—C1—C21—C26116.5 (2)C34—C35—C36—C31−0.1 (4)
C11—C1—C21—C26−6.8 (3)C21—C1—O41—C42−54.2 (2)
C31—C1—C21—C26−129.4 (2)C11—C1—O41—C4272.3 (2)
C26—C21—C22—C231.1 (4)C31—C1—O41—C42−170.96 (17)
C1—C21—C22—C23179.9 (2)C1—O41—C42—C43−164.77 (18)
C21—C22—C23—C24−0.4 (4)O41—C42—C43—N44−76.6 (2)
C22—C23—C24—C25−0.4 (5)C42—C43—N44—C45−177.2 (2)
C23—C24—C25—C260.4 (4)C42—C43—N44—C4658.2 (3)
C22—C21—C26—C25−1.1 (4)O11A—C1A—C2A—O2A−161.60 (19)
C1—C21—C26—C25−179.8 (2)O12A—C1A—C2A—O2A20.3 (3)
C24—C25—C26—C210.3 (4)O11A—C1A—C2A—C3A77.6 (2)
O41—C1—C31—N32179.69 (18)O12A—C1A—C2A—C3A−100.6 (2)
C21—C1—C31—N3262.0 (2)O2A—C2A—C3A—O3A−63.9 (2)
C11—C1—C31—N32−63.6 (2)C1A—C2A—C3A—O3A60.7 (2)
O41—C1—C31—C361.0 (3)O2A—C2A—C3A—C4A57.1 (2)
C21—C1—C31—C36−116.7 (2)C1A—C2A—C3A—C4A−178.33 (16)
C11—C1—C31—C36117.7 (2)O3A—C3A—C4A—O41A−2.5 (3)
C36—C31—N32—C331.1 (3)C2A—C3A—C4A—O41A−123.3 (2)
C1—C31—N32—C33−177.6 (2)O3A—C3A—C4A—O42A179.04 (18)
C31—N32—C33—C34−0.9 (4)C2A—C3A—C4A—O42A58.2 (2)
N32—C33—C34—C350.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C42—H42A···O3A0.972.523.391 (3)149
C43—H43B···O41Ai0.972.273.217 (3)165
N44—H44···O12A0.86 (3)2.23 (3)2.942 (2)140 (2)
C46—H46C···O2A0.962.513.084 (3)118
O2A—H2A1···N32ii0.89 (4)1.92 (4)2.804 (2)171 (3)
O3A—H3A1···O41A0.81 (3)2.08 (3)2.613 (2)123 (3)
O42A—H42···O12Aiii1.12 (3)1.33 (3)2.4475 (18)178 (3)
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+1; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC17H23N2O+·C4H5O6−
Mr420.45
Crystal system, space groupMonoclinic, P21
Temperature (K)295
a, b, c (Å)7.4419 (4), 18.4394 (8), 8.3517 (4)
β (°) 108.301 (5)
V (Å3)1088.09 (9)
Z2
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.35 × 0.2 × 0.15
Data collection
DiffractometerAgilent Xcalibur Eos
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2011)
Tmin, Tmax0.991, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		4562, 3539, 3228
Rint0.011
(sin θ/λ)max (Å−1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.079, 1.06
No. of reflections3539
No. of parameters290
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.11, −0.16

Computer programs: CrysAlis PRO (Agilent, 2011), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C42—H42A···O3A0.972.523.391 (3)149.3
C43—H43B···O41Ai0.972.273.217 (3)165.3
N44—H44···O12A0.86 (3)2.23 (3)2.942 (2)140 (2)
C46—H46C···O2A0.962.513.084 (3)118.1
O2A—H2A1···N32ii0.89 (4)1.92 (4)2.804 (2)171 (3)
O3A—H3A1···O41A0.81 (3)2.08 (3)2.613 (2)123 (3)
O42A—H42···O12Aiii1.12 (3)1.33 (3)2.4475 (18)178 (3)
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+1; (iii) x+1, y, z.
 

Acknowledgements

ASD thanks the University of Mysore for research facilities. HSY thanks R. L. Fine Chem., Bengaluru, for the gift sample of the title compound.

References

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 First citationParvez, M., Dalrymple, S. & Cote, A. (2001). Acta Cryst. E57, o163–o165.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 68| Part 4| April 2012| Pages o1054-o1055
doi:10.1107/S160053681200935X
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