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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 66| Part 9| September 2010| Pages o2443-o2444
https://doi.org/10.1107/S1600536810034288

Redetermination of bis­­{(1S,2S,4S,5R)-2-[(R)-hy­dr­oxy(6-meth­­oxy-4-quinol­yl)meth­yl]-5-vinyl­quinuclidinium} sulfate dihydrate

Peter Mangwala Kimpendea and Luc Van Meervelta*

aKatholieke Universiteit Leuven, Department of Chemistry, Celestijnenlaan 200F, B-3001 Leuven (Heverlee), Belgium
*Correspondence e-mail: luc.vanmeervelt@chem.kuleuven.be

(Received 30 July 2010; accepted 25 August 2010; online 28 August 2010)

The structure of the title compound, known as quinine sulfate dihydrate, 2C20H25N2O2+·SO42−·2H2O, was previously reported by Mendel [Proc. K. Ned. Akad. Wet. (1955), 58, 132–134], but only the [010] projection was determined. Hence, we have redetermined its crystal structure at 100 K using three-dimensional data. The asymmetric unit consists of a quininium cation, viz. (R)-(6-meth­oxy­quinolinium-4-yl)[(1S,2S,4S,5R)-5-vinyl­quinuclid­in­ium-2-yl]methanol, one half of a sulfate anion and a water mol­ecule. The S atom occupies a special position on a twofold axis. The packing is characterized by infinite columns, consisting of sulfate anions and water mol­ecules, linked through hydrogen bonds along the b axis, and further stabilized by hydrogen bonds to quininium cations. The quininium cations inter­act further through C—H⋯O and C—H⋯π inter­actions.

Related literature

For the biological activity of quinoline-based anti­malarial drugs, see: Chou et al. (1980[Chou, A. C., Chevli, R. & Fitch, C. D. (1980). Biochemistry, 19, 1543-1549.]). For related structures and a previous determination of the title compound, see: Mendel (1955[Mendel, H. (1955). Proc. K. Ned. Akad. Wet. 58, 132-134.]).

[Scheme 1]

Experimental

Crystal data

  • 2C20H25N2O2+·SO42−·2H2O

  • Mr = 782.94

  • Monoclinic, C 2

  • a = 20.180 (7) Å

  • b = 6.637 (2) Å

  • c = 15.316 (6) Å

  • β = 113.288 (9)°

  • V = 1884.2 (11) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 1.31 mm−1

  • T = 100 K

  • 0.24 × 0.15 × 0.04 mm
Data collection

  • Bruker SMART 6000 diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.743, Tmax = 0.949

  • 9588 measured reflections

  • 3319 independent reflections

  • 3112 reflections with I > 2σ(I)

  • Rint = 0.063
Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.095

  • S = 1.04

  • 3319 reflections

  • 251 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.29 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1339 Friedel pairs

  • Flack parameter: 0.00 (2)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C10 and N1–C5 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C11—H11⋯O4i 1.00 2.59 3.584 (3) 171
C16—H16A⋯O3 0.99 2.36 3.345 (3) 176
C17—H17B⋯O2ii 0.99 2.33 3.174 (3) 143
N2—H2N⋯O5 0.93 1.77 2.698 (3) 175
O2—H2⋯O3 0.84 1.87 2.695 (2) 166
O3—H3A⋯O5iii 0.86 1.99 2.765 (3) 149
O3—H3B⋯O4 0.86 1.97 2.794 (3) 159
C6—H6⋯Cg2iv 0.95 2.67 3.482 (3) 144
C20—H20B⋯Cg1v 0.95 2.85 3.530 (3) 130
Symmetry codes: (i) -x+1, y, -z+2; (ii) x, y-1, z; (iii) x, y+1, z; (iv) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+1]; (v) [x-{\script{1\over 2}}, y-{\script{1\over 2}}, z].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLUTON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810034288/lx2164sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810034288/lx2164Isup2.hkl

checkCIF report


Comment top

Malaria is the most widespread and deadly humain infectious disease that is presently endemic in tropical and subtropical countries, covering approximately half of the world population. Its treatement is sometimes complicated with the appearence of antimalarial-resistant Plasmodium falciparum strains, arising in regions due to a long time use of a specific antimalarial drug molecule. Quinine, a quinoline core alkaloid extracted from the bark of cinchona tree, is considered in certain countries as medication of last resort against malaria and it is solely used to fight parasite strains that had resisted to other available antimalarial drug molecules.

According to Chou et al. (1980) the biological activity of quinoline-based antimalarial drugs is based on the formation of cytotoxic complexes between the latter molecules and ferriprotoporphyrin IX (hematin or hemin). The knowledge of the three-dimensional structure of such complexes should be a significant step towards the elucidation of its mechanism of action and the design of new antimalarial drugs. In an attempt to crystallize porphyrin-quinine complexes, quinine sulfate dihyrate was cocrystallized with the acidic form of [Fe(III) meso-tetra(4-sulfonatophenyl)porphine]chloride at pH 4.8 from a water/propyleneglycol mixture. However, the title compound was obtained of which the [010] projection of the crystal structure has previously been determined (Mendel, 1955). Hence, we have redetermined the structure at 100 K (Fig. 1).

The unit cell comprises two formula units; each of them consists of one sulfate anion, two water molecules, and two quininium cations, (R)-(6-methoxyquinolinium-4-yl)[(1S,2S,4S,5R)-5-vinylquinuclidinium-2-yl]methanol. The sulfur atom occupies a special position on a twofold axis; both cations are related by a twofold axis. The quinoline ring is planar; the maximal deviation (0.026 (2) Å) from the best plane is observed for C10. The angle between the best planes through the quinoline rings of both cations is 58.8 (1)°. The packing is characterized by infinite columns along the b-axis, in which sulfate anions and water molecules are alternately tied together through hydrogen bonds O3—H3B···04 and O3—H3A···O5 (Fig. 2, Table 1). These columns interact further with the quininium cations by hydrogen bonding (N2—H2N···O5, O2—H2···O3, C16—H16A···O3, C11—H11···O4; Table 1). The quininium cations interact further with each other by C—H···π (Fig. 3, Table 1) interactions and a C—H···O interaction (C17—H17B···O24; Table 1).

Related literature top

For the biological activity of quinoline-based antimalarial drugs, see: Chou et al. (1980). For related structures and a previous determination of the title compound, see: Mendel (1955).

Experimental top

Quinine sulfate dihydrate, purchased from Acros Organics (Geel, Belgium), was added to the acid form of [Fe(III)meso-tetra(4-sulfonatophenyl)porphine]chloride (FeTSPP) in the mixture of water and propyleneglycol 6:4 to induce reaction between the two compounds at room temperature. The pH was fixed at 4.8 using 0.01 M acetate buffer and adjusted with either HCl or NaOH. Colourless plate-like crystals, suitable for X-ray diffraction, were obtained within five to six h.

Refinement top

Hydrogen atoms attached to N2 and O3 were located in a difference Fourier map. The other hydrogen atoms were positioned with idealized geometry using a riding model with C—H = 0.95–0.99 Å. All hydrogen atoms were further refined with isotropic temperature factors fixed at 1.2 or 1.5 times Ueq of the parent atoms.

Structure description top

Malaria is the most widespread and deadly humain infectious disease that is presently endemic in tropical and subtropical countries, covering approximately half of the world population. Its treatement is sometimes complicated with the appearence of antimalarial-resistant Plasmodium falciparum strains, arising in regions due to a long time use of a specific antimalarial drug molecule. Quinine, a quinoline core alkaloid extracted from the bark of cinchona tree, is considered in certain countries as medication of last resort against malaria and it is solely used to fight parasite strains that had resisted to other available antimalarial drug molecules.

According to Chou et al. (1980) the biological activity of quinoline-based antimalarial drugs is based on the formation of cytotoxic complexes between the latter molecules and ferriprotoporphyrin IX (hematin or hemin). The knowledge of the three-dimensional structure of such complexes should be a significant step towards the elucidation of its mechanism of action and the design of new antimalarial drugs. In an attempt to crystallize porphyrin-quinine complexes, quinine sulfate dihyrate was cocrystallized with the acidic form of [Fe(III) meso-tetra(4-sulfonatophenyl)porphine]chloride at pH 4.8 from a water/propyleneglycol mixture. However, the title compound was obtained of which the [010] projection of the crystal structure has previously been determined (Mendel, 1955). Hence, we have redetermined the structure at 100 K (Fig. 1).

The unit cell comprises two formula units; each of them consists of one sulfate anion, two water molecules, and two quininium cations, (R)-(6-methoxyquinolinium-4-yl)[(1S,2S,4S,5R)-5-vinylquinuclidinium-2-yl]methanol. The sulfur atom occupies a special position on a twofold axis; both cations are related by a twofold axis. The quinoline ring is planar; the maximal deviation (0.026 (2) Å) from the best plane is observed for C10. The angle between the best planes through the quinoline rings of both cations is 58.8 (1)°. The packing is characterized by infinite columns along the b-axis, in which sulfate anions and water molecules are alternately tied together through hydrogen bonds O3—H3B···04 and O3—H3A···O5 (Fig. 2, Table 1). These columns interact further with the quininium cations by hydrogen bonding (N2—H2N···O5, O2—H2···O3, C16—H16A···O3, C11—H11···O4; Table 1). The quininium cations interact further with each other by C—H···π (Fig. 3, Table 1) interactions and a C—H···O interaction (C17—H17B···O24; Table 1).

For the biological activity of quinoline-based antimalarial drugs, see: Chou et al. (1980). For related structures and a previous determination of the title compound, see: Mendel (1955).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLUTON (Spek, 2009) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. N—H···O and O—H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x + 1, y, - z + 2; (ii) x, y - 1, z; (iii) x, y + 1, z]
[Figure 3] Fig. 3. C—H···π interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroid. [Symmetry codes: (iv) -x + 1/2, y + 1/2, -z + 1; (v) x - 1/2, y - 1/2, z; (vi) -x + 1/2, y - 1/2, -z + 1; (vii) x + 1/2, y + 1/2, z]
bis{(1S,2S,4S,5R)-2-[(R)-hydroxy(6-methoxy- 4-quinolyl)methyl]-5-vinylquinuclidinium} sulfate dihydrate top
Crystal data top
2C20H25N2O2+·SO42−·2H2OF(000) = 836
Mr = 782.94Dx = 1.380 Mg m−3
Monoclinic, C2Cu Kα radiation, λ = 1.54178 Å
Hall symbol: C 2yCell parameters from 3041 reflections
a = 20.180 (7) Åθ = 3.1–70.8°
b = 6.637 (2) ŵ = 1.31 mm−1
c = 15.316 (6) ÅT = 100 K
β = 113.288 (9)°Plate, colourless
V = 1884.2 (11) Å30.24 × 0.15 × 0.04 mm
Z = 2
Data collection top
Bruker SMART 6000
diffractometer		3319 independent reflections
Radiation source: fine-focus sealed tube3112 reflections with I > 2σ(I)
Crossed Globel mirrors monochromatorRint = 0.063
ω and φ scanθmax = 70.7°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)		h = −24→23
Tmin = 0.743, Tmax = 0.949k = −8→7
9588 measured reflectionsl = −18→18
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0484P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3319 reflectionsΔρmax = 0.32 e Å−3
251 parametersΔρmin = −0.29 e Å−3
1 restraintAbsolute structure: Flack (1983), 1339 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (2)
Crystal data top
2C20H25N2O2+·SO42−·2H2OV = 1884.2 (11) Å3
Mr = 782.94Z = 2
Monoclinic, C2Cu Kα radiation
a = 20.180 (7) ŵ = 1.31 mm−1
b = 6.637 (2) ÅT = 100 K
c = 15.316 (6) Å0.24 × 0.15 × 0.04 mm
β = 113.288 (9)°
Data collection top
Bruker SMART 6000
diffractometer		3319 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)		3112 reflections with I > 2σ(I)
Tmin = 0.743, Tmax = 0.949Rint = 0.063
9588 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.095Δρmax = 0.32 e Å−3
S = 1.04Δρmin = −0.29 e Å−3
3319 reflectionsAbsolute structure: Flack (1983), 1339 Friedel pairs
251 parametersAbsolute structure parameter: 0.00 (2)
1 restraint
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
S10.50000.51309 (11)1.00000.01395 (17)
O10.47279 (8)0.1096 (3)0.69000 (11)0.0189 (3)
O20.32201 (8)0.9132 (3)0.79914 (10)0.0157 (3)
H20.35330.94430.85280.024*
O30.40574 (8)0.9948 (3)0.98222 (10)0.0203 (3)
H3A0.43081.10280.98750.024*
H3B0.43780.90421.00970.024*
O40.47838 (9)0.6396 (3)1.06305 (11)0.0224 (4)
O50.43932 (8)0.3783 (3)0.94218 (11)0.0189 (4)
C10.48547 (12)0.0841 (4)0.78784 (16)0.0209 (5)
H1A0.51640.19340.82520.031*
H1B0.5094−0.04560.81040.031*
H1C0.43940.08690.79510.031*
C20.43495 (11)0.2754 (4)0.64592 (15)0.0147 (4)
C30.42548 (11)0.2932 (4)0.54931 (15)0.0178 (5)
H30.44230.18990.52030.021*
C40.39215 (11)0.4589 (4)0.49829 (15)0.0185 (5)
H40.38740.47120.43430.022*
C50.36455 (11)0.6127 (4)0.53810 (15)0.0163 (4)
C60.30432 (11)0.9131 (4)0.52007 (15)0.0167 (4)
H60.28191.02680.48230.020*
C70.30701 (11)0.9037 (4)0.61389 (15)0.0156 (4)
H70.28591.00760.63700.019*
C80.34015 (11)0.7442 (4)0.67093 (14)0.0141 (4)
C90.37165 (10)0.5906 (4)0.63416 (15)0.0141 (4)
C100.40826 (10)0.4200 (4)0.68725 (14)0.0145 (4)
H100.41430.40600.75170.017*
C110.34041 (11)0.7262 (4)0.77006 (14)0.0138 (4)
H110.38960.68520.81570.017*
C120.28570 (10)0.5609 (3)0.76677 (14)0.0132 (4)
H120.29280.44570.72930.016*
C130.20590 (10)0.6274 (4)0.71813 (14)0.0150 (4)
H13A0.20340.77280.70280.018*
H13B0.18180.55190.65810.018*
C140.16724 (11)0.5862 (4)0.78526 (15)0.0161 (5)
H140.11550.62820.75390.019*
C150.20490 (12)0.7091 (4)0.87635 (16)0.0181 (5)
H15A0.17790.69710.91780.022*
H15B0.20640.85300.86040.022*
C160.28208 (11)0.6285 (4)0.92844 (14)0.0166 (4)
H16A0.31690.74160.94500.020*
H16B0.28640.56050.98800.020*
C170.25215 (11)0.2979 (4)0.85222 (15)0.0159 (5)
H17A0.26510.22790.91380.019*
H17B0.26010.20380.80720.019*
C180.17165 (11)0.3630 (4)0.81314 (15)0.0154 (5)
H180.15380.34830.86520.018*
C190.12712 (12)0.2289 (4)0.73183 (16)0.0216 (5)
H190.13650.23260.67570.026*
C200.07601 (13)0.1066 (4)0.73313 (19)0.0281 (6)
H20A0.06520.09910.78810.034*
H20B0.05000.02600.67910.034*
N10.33113 (10)0.7734 (3)0.48223 (13)0.0185 (4)
N20.29863 (9)0.4822 (3)0.86512 (12)0.0134 (4)
H2N0.34670.44380.89480.016*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0136 (3)0.0123 (4)0.0143 (3)0.0000.0038 (3)0.000
O10.0200 (7)0.0183 (9)0.0194 (7)0.0051 (6)0.0089 (6)0.0009 (7)
O20.0184 (7)0.0137 (8)0.0128 (6)0.0003 (6)0.0039 (6)−0.0020 (6)
O30.0190 (7)0.0168 (8)0.0208 (7)0.0013 (7)0.0032 (6)0.0005 (7)
O40.0266 (8)0.0199 (9)0.0218 (8)0.0033 (7)0.0108 (7)−0.0009 (7)
O50.0150 (8)0.0146 (9)0.0226 (8)0.0019 (6)0.0024 (6)0.0014 (7)
C10.0204 (10)0.0243 (13)0.0195 (10)0.0045 (9)0.0094 (9)0.0054 (10)
C20.0112 (9)0.0147 (12)0.0187 (10)−0.0007 (8)0.0064 (8)0.0003 (9)
C30.0189 (10)0.0187 (12)0.0196 (10)−0.0018 (9)0.0114 (9)−0.0040 (10)
C40.0195 (10)0.0236 (14)0.0143 (9)−0.0032 (9)0.0087 (8)−0.0021 (9)
C50.0144 (9)0.0180 (12)0.0160 (10)−0.0019 (9)0.0055 (8)0.0009 (10)
C60.0158 (10)0.0165 (11)0.0161 (10)−0.0013 (9)0.0044 (8)0.0032 (9)
C70.0154 (9)0.0144 (11)0.0175 (10)−0.0004 (9)0.0070 (8)0.0010 (9)
C80.0105 (9)0.0158 (11)0.0143 (9)−0.0032 (8)0.0030 (7)−0.0004 (9)
C90.0107 (9)0.0167 (11)0.0146 (9)−0.0045 (8)0.0047 (8)−0.0022 (9)
C100.0128 (9)0.0194 (12)0.0128 (9)−0.0024 (9)0.0066 (8)−0.0001 (9)
C110.0140 (10)0.0133 (11)0.0142 (9)0.0017 (8)0.0056 (8)−0.0015 (9)
C120.0142 (9)0.0167 (12)0.0100 (9)0.0004 (8)0.0063 (7)−0.0005 (8)
C130.0131 (9)0.0182 (12)0.0128 (9)−0.0002 (8)0.0042 (8)0.0009 (9)
C140.0117 (9)0.0210 (13)0.0149 (9)0.0028 (9)0.0046 (8)−0.0004 (9)
C150.0211 (11)0.0161 (12)0.0199 (10)0.0006 (9)0.0110 (9)−0.0025 (10)
C160.0209 (10)0.0161 (12)0.0130 (9)−0.0034 (9)0.0069 (8)−0.0024 (9)
C170.0195 (10)0.0114 (11)0.0175 (10)−0.0008 (9)0.0082 (8)0.0005 (9)
C180.0151 (10)0.0180 (12)0.0157 (10)−0.0041 (8)0.0090 (8)−0.0018 (9)
C190.0220 (11)0.0215 (13)0.0221 (11)−0.0040 (10)0.0096 (9)−0.0046 (10)
C200.0257 (12)0.0260 (15)0.0348 (13)−0.0075 (11)0.0144 (10)−0.0085 (12)
N10.0176 (8)0.0223 (11)0.0157 (8)−0.0016 (8)0.0066 (7)0.0018 (8)
N20.0114 (7)0.0144 (10)0.0144 (8)0.0000 (7)0.0050 (6)0.0027 (8)
Geometric parameters (Å, º) top
S1—O41.4703 (17)C10—H100.9500
S1—O4i1.4703 (17)C11—C121.543 (3)
S1—O5i1.4923 (16)C11—H111.0000
S1—O51.4923 (16)C12—N21.517 (3)
O1—C21.357 (3)C12—C131.547 (3)
O1—C11.427 (3)C12—H121.0000
O2—C111.417 (3)C13—C141.541 (3)
O2—H20.8400C13—H13A0.9900
O3—H3A0.8626C13—H13B0.9900
O3—H3B0.8622C14—C151.533 (3)
C1—H1A0.9800C14—C181.535 (4)
C1—H1B0.9800C14—H141.0000
C1—H1C0.9800C15—C161.538 (3)
C2—C101.372 (3)C15—H15A0.9900
C2—C31.420 (3)C15—H15B0.9900
C3—C41.362 (4)C16—N21.500 (3)
C3—H30.9500C16—H16A0.9900
C4—C51.412 (3)C16—H16B0.9900
C4—H40.9500C17—N21.506 (3)
C5—N11.367 (3)C17—C181.554 (3)
C5—C91.428 (3)C17—H17A0.9900
C6—N11.317 (3)C17—H17B0.9900
C6—C71.418 (3)C18—C191.505 (3)
C6—H60.9500C18—H181.0000
C7—C81.367 (3)C19—C201.319 (4)
C7—H70.9500C19—H190.9500
C8—C91.429 (3)C20—H20A0.9500
C8—C111.521 (3)C20—H20B0.9500
C9—C101.419 (3)N2—H2N0.9300
O4—S1—O4i110.34 (12)C11—C12—H12107.4
O4—S1—O5i109.85 (9)C13—C12—H12107.4
O4i—S1—O5i110.20 (9)C14—C13—C12109.47 (17)
O4—S1—O5110.20 (9)C14—C13—H13A109.8
O4i—S1—O5109.85 (9)C12—C13—H13A109.8
O5i—S1—O5106.33 (11)C14—C13—H13B109.8
C2—O1—C1116.78 (18)C12—C13—H13B109.8
C11—O2—H2109.5H13A—C13—H13B108.2
H3A—O3—H3B103.5C15—C14—C18107.87 (18)
O1—C1—H1A109.5C15—C14—C13108.27 (18)
O1—C1—H1B109.5C18—C14—C13111.57 (18)
H1A—C1—H1B109.5C15—C14—H14109.7
O1—C1—H1C109.5C18—C14—H14109.7
H1A—C1—H1C109.5C13—C14—H14109.7
H1B—C1—H1C109.5C14—C15—C16108.85 (18)
O1—C2—C10125.74 (19)C14—C15—H15A109.9
O1—C2—C3113.79 (19)C16—C15—H15A109.9
C10—C2—C3120.5 (2)C14—C15—H15B109.9
C4—C3—C2119.8 (2)C16—C15—H15B109.9
C4—C3—H3120.1H15A—C15—H15B108.3
C2—C3—H3120.1N2—C16—C15109.17 (17)
C3—C4—C5121.70 (19)N2—C16—H16A109.8
C3—C4—H4119.2C15—C16—H16A109.8
C5—C4—H4119.2N2—C16—H16B109.8
N1—C5—C4118.38 (19)C15—C16—H16B109.8
N1—C5—C9123.3 (2)H16A—C16—H16B108.3
C4—C5—C9118.4 (2)N2—C17—C18109.07 (18)
N1—C6—C7123.8 (2)N2—C17—H17A109.9
N1—C6—H6118.1C18—C17—H17A109.9
C7—C6—H6118.1N2—C17—H17B109.9
C8—C7—C6119.7 (2)C18—C17—H17B109.9
C8—C7—H7120.2H17A—C17—H17B108.3
C6—C7—H7120.2C19—C18—C14113.00 (19)
C7—C8—C9118.79 (19)C19—C18—C17110.20 (19)
C7—C8—C11120.4 (2)C14—C18—C17108.20 (18)
C9—C8—C11120.7 (2)C19—C18—H18108.4
C10—C9—C5119.3 (2)C14—C18—H18108.4
C10—C9—C8123.71 (19)C17—C18—H18108.4
C5—C9—C8117.0 (2)C20—C19—C18124.5 (2)
C2—C10—C9120.28 (19)C20—C19—H19117.8
C2—C10—H10119.9C18—C19—H19117.8
C9—C10—H10119.9C19—C20—H20A120.0
O2—C11—C8110.29 (18)C19—C20—H20B120.0
O2—C11—C12111.09 (16)H20A—C20—H20B120.0
C8—C11—C12107.66 (17)C6—N1—C5117.42 (18)
O2—C11—H11109.3C16—N2—C17108.91 (16)
C8—C11—H11109.3C16—N2—C12115.10 (17)
C12—C11—H11109.3C17—N2—C12107.21 (16)
N2—C12—C11111.88 (16)C16—N2—H2N108.5
N2—C12—C13108.31 (15)C17—N2—H2N108.5
C11—C12—C13114.11 (19)C12—N2—H2N108.5
N2—C12—H12107.4
C1—O1—C2—C100.3 (3)O2—C11—C12—C1345.5 (2)
C1—O1—C2—C3178.89 (18)C8—C11—C12—C13−75.4 (2)
O1—C2—C3—C4−176.14 (19)N2—C12—C13—C14−1.2 (3)
C10—C2—C3—C42.6 (3)C11—C12—C13—C14−126.55 (19)
C2—C3—C4—C5−1.9 (3)C12—C13—C14—C1560.7 (2)
C3—C4—C5—N1−179.3 (2)C12—C13—C14—C18−57.9 (2)
C3—C4—C5—C9−0.6 (3)C18—C14—C15—C1655.2 (2)
N1—C6—C7—C81.3 (3)C13—C14—C15—C16−65.7 (2)
C6—C7—C8—C90.2 (3)C14—C15—C16—N29.5 (2)
C6—C7—C8—C11−177.01 (19)C15—C14—C18—C19171.51 (16)
N1—C5—C9—C10−179.0 (2)C13—C14—C18—C19−69.7 (2)
C4—C5—C9—C102.3 (3)C15—C14—C18—C17−66.2 (2)
N1—C5—C9—C81.6 (3)C13—C14—C18—C1752.6 (2)
C4—C5—C9—C8−177.13 (19)N2—C17—C18—C19133.72 (19)
C7—C8—C9—C10179.07 (19)N2—C17—C18—C149.7 (2)
C11—C8—C9—C10−3.7 (3)C14—C18—C19—C20−123.4 (3)
C7—C8—C9—C5−1.5 (3)C17—C18—C19—C20115.4 (3)
C11—C8—C9—C5175.70 (18)C7—C6—N1—C5−1.3 (3)
O1—C2—C10—C9177.73 (19)C4—C5—N1—C6178.53 (19)
C3—C2—C10—C9−0.8 (3)C9—C5—N1—C6−0.2 (3)
C5—C9—C10—C2−1.6 (3)C15—C16—N2—C17−67.5 (2)
C8—C9—C10—C2177.8 (2)C15—C16—N2—C1252.9 (2)
C7—C8—C11—O2−16.4 (3)C18—C17—N2—C1655.8 (2)
C9—C8—C11—O2166.46 (18)C18—C17—N2—C12−69.36 (19)
C7—C8—C11—C12105.0 (2)C11—C12—N2—C1669.1 (2)
C9—C8—C11—C12−72.2 (2)C13—C12—N2—C16−57.5 (2)
O2—C11—C12—N2−78.0 (2)C11—C12—N2—C17−169.59 (17)
C8—C11—C12—N2161.20 (17)C13—C12—N2—C1763.8 (2)
Symmetry code: (i) −x+1, y, −z+2.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C2–C10 and N1–C5 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C11—H11···O4i1.002.593.584 (3)171
C16—H16A···O30.992.363.345 (3)176
C17—H17B···O2ii0.992.333.174 (3)143
N2—H2N···O50.931.772.698 (3)175
O2—H2···O30.841.872.695 (2)166
O3—H3A···O5iii0.861.992.765 (3)149
O3—H3B···O40.861.972.794 (3)159
C6—H6···Cg2iv0.952.673.482 (3)144
C20—H20B···Cg1v0.952.853.530 (3)130
Symmetry codes: (i) −x+1, y, −z+2; (ii) x, y−1, z; (iii) x, y+1, z; (iv) −x+1/2, y+1/2, −z+1; (v) x−1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula2C20H25N2O2+·SO42−·2H2O
Mr782.94
Crystal system, space groupMonoclinic, C2
Temperature (K)100
a, b, c (Å)20.180 (7), 6.637 (2), 15.316 (6)
β (°) 113.288 (9)
V (Å3)1884.2 (11)
Z2
Radiation typeCu Kα
µ (mm−1)1.31
Crystal size (mm)0.24 × 0.15 × 0.04
Data collection
DiffractometerBruker SMART 6000
Absorption correctionMulti-scan
(SADABS; Bruker, 2003)
Tmin, Tmax0.743, 0.949
No. of measured, independent and
observed [I > 2σ(I)] reflections		9588, 3319, 3112
Rint0.063
(sin θ/λ)max (Å−1)0.612
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.095, 1.04
No. of reflections3319
No. of parameters251
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.32, −0.29
Absolute structureFlack (1983), 1339 Friedel pairs
Absolute structure parameter0.00 (2)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLUTON (Spek, 2009) and DIAMOND (Brandenburg, 2010), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C2–C10 and N1–C5 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C11—H11···O4i1.002.593.584 (3)171
C16—H16A···O30.992.363.345 (3)176
C17—H17B···O2ii0.992.333.174 (3)143
N2—H2N···O50.931.772.698 (3)175
O2—H2···O30.841.872.695 (2)166
O3—H3A···O5iii0.861.992.765 (3)149
O3—H3B···O40.861.972.794 (3)159
C6—H6···Cg2iv0.952.673.482 (3)144
C20—H20B···Cg1v0.952.853.530 (3)130
Symmetry codes: (i) −x+1, y, −z+2; (ii) x, y−1, z; (iii) x, y+1, z; (iv) −x+1/2, y+1/2, −z+1; (v) x−1/2, y−1/2, z.
 

Acknowledgements

The authors thank the Katholieke Universiteit Leuven for financial support and K. Van Hecke, M. Ovaere and K. Robeyns for help and discussions.

References

First citationBrandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2003). SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChou, A. C., Chevli, R. & Fitch, C. D. (1980). Biochemistry, 19, 1543–1549.  CAS PubMed Web of Science Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationMendel, H. (1955). Proc. K. Ned. Akad. Wet. 58, 132–134.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 9| September 2010| Pages o2443-o2444
https://doi.org/10.1107/S1600536810034288
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