Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 2| February 2011| Pages o500-o501
doi:10.1107/S1600536811002674

Cinnarizinium dipicrate

Jerry P. Jasinski,a* Ray J. Butcher,b M. S. Siddegowda,c H. S. Yathirajanc and C. S. Chidan Kumarc

aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
*Correspondence e-mail: jjasinski@keene.edu

(Received 30 December 2010; accepted 19 January 2011; online 26 January 2011)

In the cinnarizinium dication of the title compound {systematic name: 1-diphenyl­methyl-4-[(2E)-3-phenyl­prop-2-en-1-yl]piperazine-1,4-diium bis­(2,4,6-trinitro­phenolate)}, C26H30N22+·2C6H2N3O7−, the piperazine group is protonated at both N atoms and adopts a slightly distorted chair conformation. Strong N—H⋯Ohy­droxy cation–anion hydrogen bonds link the dication and two anions. In the cation, the (2E)-3-phenyl­prop-2-en-1-yl fragment is disordered over two positions in a ratio of 0.586 (4): 0.414 (4). Two nitro groups in one anion and three in the other one demonstrate rotational disorder. The crystal packing is stabilized by weak inter­molecular π–π [centroid–centroid distances = 3.844 (7), 3.677 (9), 3.825 (5), 3.634 (2) and 3.729 (7) Å], C—H⋯π and C—H⋯O inter­actions.

Related literature

For background to the anti­histamine cinnarizine (systematic name: 1-benzhydryl-4-cinnamyl-piperazine), see: Barrett & Zolov (1960[Barrett, R. J. & Zolov, B. (1960). J. Maine Med. Assoc. 51, 454-457.]); Towse (1980[Towse, G. (1980). J. Laryngol. Otol. 94, 1009-1015.]). For the structure of opipramol dipicrate {systematic name: 1-[3-(5H-dibenz[b,f]azepin-5-yl)prop­yl]-4-(2-hy­droxy­eth­yl)piperazine-1,4-diium bis­(2,4,6-tri­nitro­phrenolate)}, see: Jasinski et al. (2010[Jasinski, J. P., Pek, A. E., Siddaraju, B. P., Yathirajan, H. S. & Narayana, B. (2010). Acta Cryst. E66, o1979-o1980.]). For related structures, see: Bertolasi et al. (1980[Bertolasi, V., Borea, P. A., Gilli, G. & Sacerdoti, M. (1980). Acta Cryst. B36, 1975-1977.]); Mouillé et al. (1975[Mouillé, Y., Cotrait, M., Hospital, M. & Marsau, P. (1975). Acta Cryst. B31, 1495-1496.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem, Soc. 97, 1354-1358.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C26H30N22+·2C6H2N3O7−

  • Mr = 826.73

  • Monoclinic, P 21 /c

  • a = 15.1987 (2) Å

  • b = 10.09130 (17) Å

  • c = 25.0724 (3) Å

  • β = 95.9170 (14)°

  • V = 3824.98 (10) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.95 mm−1

  • T = 295 K

  • 0.49 × 0.42 × 0.27 mm
Data collection

  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.777, Tmax = 1.000

  • 14786 measured reflections

  • 7319 independent reflections

  • 5784 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.092

  • wR(F2) = 0.289

  • S = 1.01

  • 7319 reflections

  • 648 parameters

  • 40 restraints

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

  • Δρmax = 1.24 e Å−3

  • Δρmin = −0.48 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg5 and Cg6 are the centroids of the C6–C11 and C12–C17 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O1A 0.90 (1) 1.77 (1) 2.658 (3) 168 (3)
N2—H2N⋯O1B 0.90 (1) 1.83 (3) 2.603 (3) 143 (4)
N2—H2N⋯O7BA 0.90 (1) 2.30 (3) 3.047 (5) 140 (3)
C3—H3A⋯O2AA 0.97 2.50 3.214 (8) 130
C3—H3A⋯O2AB 0.97 2.52 3.242 (17) 131
C2—H2B⋯O7AA 0.97 2.48 3.304 (5) 142
C2—H2B⋯O7AB 0.97 2.54 3.42 (4) 151
C11—H11A⋯O4BAi 0.93 2.57 3.244 (4) 130
C17—H17A⋯O1A 0.93 2.62 3.473 (4) 154
C17—H17A⋯O5BBi 0.93 2.52 3.267 (8) 138
C18A—H18A⋯Cg6ii 0.97 2.88 3.742 (5) 148
C18A—H18B⋯Cg5ii 0.97 2.83 3.762 (1) 161
C18A—H18C⋯Cg5ii 0.97 3.00 3.762 (1) 137
C18A—H18D⋯Cg6ii 0.97 2.84 3.742 (5) 155
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) x, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002674/cv5030sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811002674/cv5030Isup2.hkl

checkCIF report


Comment top

Cinnarizine is an antihistamine which is mainly used for the control of nausea and vomiting due to motion sickness. Cinnarizine could be also viewed as a nootropic drug because of its vasorelaxating abilities (due to calcium channel blockage), which happen mostly in brain and is also used as a labyrinthine sedative (Towse, 1980). A clinical evaluation of cinnarizine in various allergic disorders is published (Barrett & Zolov, 1960). Cinnarizine can be used in scuba divers without an increased risk of central nervous system oxygen toxicity. The crystal structures of some related compounds viz., cinnarizine (Mouillé et al., 1975) and cyclizine hydrochloride (Bertolasi et al., 1980) have been reported. In continuation of our work on the picrates of pharmaceutical compounds, we have recently reported the crystal structure of opipramol dipicrate (Jasinski et al., 2010). In view of the importance of cinnarizine, this paper reports the crystal structure of the title compound, C26H30N22+. 2(C6H2N3O7)-, (I).

In the cinnarizinium dication of the title compound, (I), [systematic name: 1-benzhydryl-4-cinnamyl-piperazine dipicrate] the piperazine group is protonated at both N atoms and adopts a slightly distorted chair conformation with puckering parameters Q, θ and ϕ of 0.58 (3) Å, 177.1 (0)° and 175.518 (5)° (Cremer & Pople, 1975) (Fig. 1). For an ideal chair θ has a value of 0 or 180°. The dihedral angle between the mean planes of the cation piperazine ring and three benzene rings or the six-membered rings of the picrate anions are 75.9 (6)° 80.0 (2)°, 80.4 (9)° or 71.4 (9)° and 86.7 (6)°, respectively. Bond distances (Allen et al., 1987) and angles are in normal ranges. Strong N—H···Ohydroxy cation-anion hydrogen bonds link the dication and two anions. In the cation, the (2E)-3-phenylprop-2-ene-1yl fragment is disordered over two positions in a ratio of 0.586 (4): 0.414 (4). Two nitro groups in one anion (A) and three in the other (B) demonstrate rotational disorder [O2AA & O3AA (0.68 (2)), O2AB & O3AB (0.32 (2)); O6AA & O7AA (0.851 (14)), O6AB & O7AB (0.149 (14)); O2BA & O3BA (0.80 (2)), O2BB & O3BB (0.20 (2)); O4BA & O5BB (0.951 (19)), O4BB & O5BB (0.050 (19)); O6BA & O7BA (0.756 (8)), O6BB & O7BB (0.244 (8))]. The crystal packing is stabilized by π–π (Table 1), C—H···π-ring and C—H···O (Table 2) weak intermolecular interactions creating a 2-D network structure (Fig. 2).

Related literature top

For background to the antihistamine cinnarizine (systematic name: 1-benzhydryl-4-cinnamyl-piperazine), see: Barrett & Zolov (1960); Towse (1980). For the structure of opipramol dipicrate {systematic name: 1-[3-(5H-dibenz[b,f]azepin-5-yl)propyl]-4-(2-hydroxyethyl)piperazine-1,4-diium bis(2,4,6-trinitrophrenolate)}, see: Jasinski et al. (2010). For related structures, see: Bertolasi et al. (1980); Mouillé et al. (1975). For puckering parametes, see: Cremer & Pople (1975). For standard bond lengths, see: Allen et al. (1987).

Experimental top

Cinnarizine (3.68 g, 0.01 mol) and picric acid (2.99 g, 0.01 mol) were dissolved in hot acetonitrile and dimethyl sulphoxide (80:20 v/v) solution and stirred over a heating magnetic stirrer for few minutes (330 K). The resulting solution was allowed to cool slowly at room temperature. X-ray quality crystals of the title compound appeared after a few days. (M.P.: 481– 483 K).

Refinement top

Carbon atoms C18–C26 are disordered (0.586 (4) A: 0.414 (4) B). The oxygen atoms on the N1A, N3A, N1B, N2B and N3B anion nitro groups are rotationally disordered [O2AA & O3AA (0.68 (2)), O2AB & O3AB (0.32 (2)); O6AA & O7AA (0.851 (14)), O6AB & O7AB (0.149 (14)); O2BA & O3BA (0.80 (2)), O2BB & O3BB (0.20 (2)); O4BA & O5BB (0.951 (19)), O4BB & O5BB (0.050 (19)); O6BA & O7BA (0.756 (8)), O6BB & O7BB (0.244 (8))] H1N and H2N were refined isotropically. All of the remaining H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.93 & 0.98Å (CH), or 0.97Å (CH2). Isotropic displacement parameters for these atoms were set to 1.19–1.20 (CH, CH2) times Ueq of the parent atom. The highest residual peak of 1.24 eÅ-3 is situated 1.16 Å from atom O1B.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 30% probability displacement ellipsoids. Dashed lines indicate strong intermolecular N—H···O hydrogen bonds between the protonated N atoms from the piperazine group in the cinnarizinium cation and the two picrate anions. For the disordered atoms, only major components are shown.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed down the a axis. Dashed lines indicate N—H···O hydrogen bonds and weak C—H···O intermolecular interactions creating a 2-D network structure.
1-diphenylmethyl-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine-1,4-diium bis(2,4,6-trinitrophenolate) top
Crystal data top
C26H30N22+·2C6H2N3O7−F(000) = 1720
Mr = 826.73Dx = 1.436 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 7661 reflections
a = 15.1987 (2) Åθ = 4.8–73.3°
b = 10.09130 (17) ŵ = 0.95 mm−1
c = 25.0724 (3) ÅT = 295 K
β = 95.9170 (14)°Chunk, yellow
V = 3824.98 (10) Å30.49 × 0.42 × 0.27 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		7319 independent reflections
Radiation source: Enhance (Cu) X-ray Source5784 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 10.5081 pixels mm-1θmax = 73.5°, θmin = 4.8°
ω scansh = −18→17
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		k = −11→12
Tmin = 0.777, Tmax = 1.000l = −31→20
14786 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.092H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.289 w = 1/[σ2(Fo2) + (0.196P)2 + 2.2706P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.007
7319 reflectionsΔρmax = 1.24 e Å−3
648 parametersΔρmin = −0.48 e Å−3
40 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0017 (4)
Crystal data top
C26H30N22+·2C6H2N3O7−V = 3824.98 (10) Å3
Mr = 826.73Z = 4
Monoclinic, P21/cCu Kα radiation
a = 15.1987 (2) ŵ = 0.95 mm−1
b = 10.09130 (17) ÅT = 295 K
c = 25.0724 (3) Å0.49 × 0.42 × 0.27 mm
β = 95.9170 (14)°
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		7319 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		5784 reflections with I > 2σ(I)
Tmin = 0.777, Tmax = 1.000Rint = 0.024
14786 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.09240 restraints
wR(F2) = 0.289H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 1.24 e Å−3
7319 reflectionsΔρmin = −0.48 e Å−3
648 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)
N10.75982 (13)0.8086 (2)0.55675 (7)0.0344 (5)
H1N0.759 (2)0.816 (3)0.5925 (3)0.044 (8)*
N20.75781 (15)0.5191 (2)0.55806 (8)0.0413 (5)
H2N0.766 (3)0.501 (4)0.5239 (5)0.062 (10)*
C10.84038 (16)0.7281 (3)0.54794 (11)0.0408 (6)
H1A0.89320.77660.56130.049*
H1B0.84220.71340.50980.049*
C20.83881 (18)0.5960 (3)0.57647 (11)0.0433 (6)
H2A0.89070.54510.56970.052*
H2B0.84100.61090.61480.052*
C30.67708 (17)0.5985 (3)0.56498 (11)0.0431 (6)
H3A0.67320.61360.60290.052*
H3B0.62500.54920.55080.052*
C40.67904 (16)0.7304 (3)0.53629 (10)0.0403 (6)
H4A0.67920.71540.49810.048*
H4B0.62630.78060.54190.048*
C50.76219 (17)0.9422 (3)0.52874 (9)0.0384 (6)
H5A0.76620.92460.49060.046*
C60.67862 (17)1.0214 (3)0.53265 (10)0.0394 (6)
C70.6353 (2)1.0759 (3)0.48662 (12)0.0526 (7)
H7A0.65411.05530.45350.063*
C80.5645 (2)1.1607 (4)0.48926 (15)0.0671 (9)
H8A0.53641.19730.45800.080*
C90.5356 (2)1.1908 (4)0.53768 (15)0.0618 (9)
H9A0.48881.24940.53950.074*
C100.5762 (2)1.1342 (4)0.58369 (14)0.0582 (8)
H10A0.55511.15190.61650.070*
C110.6478 (2)1.0515 (3)0.58150 (11)0.0497 (7)
H11A0.67571.01540.61290.060*
C120.84287 (18)1.0223 (3)0.54911 (11)0.0425 (6)
C130.8878 (2)1.0922 (4)0.51268 (15)0.0679 (10)
H13A0.87191.08120.47610.081*
C140.9559 (3)1.1782 (5)0.5300 (2)0.0871 (14)
H14A0.98431.22590.50510.105*
C150.9817 (2)1.1931 (5)0.5837 (2)0.0811 (13)
H15A1.02761.25040.59520.097*
C160.9390 (2)1.1228 (4)0.62025 (16)0.0675 (9)
H16A0.95711.13140.65670.081*
C170.8696 (2)1.0395 (3)0.60355 (12)0.0524 (7)
H17A0.84030.99440.62880.063*
C18A0.7558 (2)0.3854 (3)0.58610 (13)0.0561 (8)0.586 (4)
H18A0.81310.34310.58580.067*0.586 (4)
H18B0.71220.32920.56620.067*0.586 (4)
C19A0.7334 (4)0.3969 (6)0.6447 (3)0.0529 (11)0.586 (4)
H19A0.67480.40710.65150.063*0.586 (4)
C20A0.7955 (4)0.3926 (5)0.6849 (2)0.0520 (10)0.586 (4)
H20A0.85290.38490.67550.062*0.586 (4)
C21A0.7875 (8)0.3981 (12)0.7433 (4)0.053 (3)0.586 (4)
C22A0.8612 (7)0.3990 (12)0.7805 (5)0.058 (2)0.586 (4)
H22A0.91770.40000.76930.070*0.586 (4)
C23A0.8507 (14)0.398 (2)0.8307 (10)0.066 (5)0.586 (4)
H23A0.90110.39960.85510.079*0.586 (4)
C24A0.7726 (14)0.3958 (14)0.8500 (8)0.068 (7)0.586 (4)
H24A0.77390.38560.88690.082*0.586 (4)
C25A0.691 (2)0.406 (3)0.8224 (14)0.079 (8)0.586 (4)
H25A0.63720.41520.83690.094*0.586 (4)
C26A0.7035 (14)0.401 (3)0.7669 (14)0.072 (5)0.586 (4)
H26A0.65250.39950.74300.086*0.586 (4)
C18B0.7558 (2)0.3854 (3)0.58610 (13)0.0561 (8)0.414 (4)
H18C0.69600.35070.58150.067*0.414 (4)
H18D0.79360.32380.56930.067*0.414 (4)
C19B0.7860 (6)0.3939 (8)0.6445 (4)0.0529 (11)0.414 (4)
H19B0.84600.39970.65610.063*0.414 (4)
C20B0.7274 (6)0.3932 (8)0.6793 (3)0.0520 (10)0.414 (4)
H20B0.66790.38880.66630.062*0.414 (4)
C21B0.7502 (10)0.3992 (16)0.7386 (4)0.044 (3)0.414 (4)
C22B0.8333 (9)0.3969 (16)0.7670 (6)0.051 (3)0.414 (4)
H22B0.88370.39420.74890.061*0.414 (4)
C23B0.841 (3)0.399 (3)0.826 (2)0.104 (14)0.414 (4)
H23B0.89750.39760.84420.125*0.414 (4)
C24B0.771 (2)0.402 (2)0.8544 (11)0.071 (10)0.414 (4)
H24B0.77240.40880.89150.085*0.414 (4)
C25B0.694 (3)0.395 (3)0.8183 (13)0.050 (5)0.414 (4)
H25B0.64290.38480.83510.060*0.414 (4)
C26B0.6787 (18)0.400 (3)0.7629 (13)0.052 (4)0.414 (4)
H26B0.62220.40290.74470.062*0.414 (4)
O1A0.7492 (2)0.7961 (3)0.66177 (8)0.0704 (7)
O2AA0.5803 (8)0.7737 (14)0.64870 (13)0.108 (3)0.68 (2)
O3AA0.5075 (5)0.803 (2)0.7157 (4)0.169 (5)0.68 (2)
O2AB0.5627 (18)0.742 (3)0.6507 (4)0.108 (3)0.32 (2)
O3AB0.5305 (13)0.863 (2)0.7152 (11)0.169 (5)0.32 (2)
O4A0.64470 (17)0.7000 (3)0.89225 (10)0.0867 (9)
O5A0.78481 (17)0.7067 (3)0.90778 (9)0.0809 (9)
O6AA0.9618 (2)0.7918 (10)0.76971 (16)0.134 (3)0.851 (14)
O7AA0.9173 (3)0.7450 (11)0.68875 (15)0.143 (3)0.851 (14)
O6AB0.9535 (15)0.851 (2)0.7519 (13)0.134 (3)0.149 (14)
O7AB0.924 (2)0.680 (4)0.7036 (18)0.143 (3)0.149 (14)
N1A0.57602 (18)0.7801 (4)0.69661 (10)0.0703 (8)
N2A0.71761 (14)0.7114 (3)0.87725 (8)0.0593 (7)
N3A0.90351 (17)0.7638 (4)0.73487 (10)0.0758 (9)
C1A0.7410 (2)0.7722 (3)0.70954 (10)0.0431 (6)
C2A0.6581 (2)0.7630 (3)0.73172 (11)0.0462 (6)
C3A0.6493 (2)0.7436 (3)0.78570 (12)0.0493 (7)
H3AA0.59360.73960.79790.059*
C4A0.7242 (2)0.7305 (3)0.82064 (10)0.0453 (6)
C5A0.8072 (2)0.7370 (3)0.80328 (11)0.0478 (7)
H5AA0.85740.72860.82760.057*
C6A0.8152 (2)0.7560 (3)0.74985 (11)0.0474 (7)
O1B0.7062 (2)0.4822 (4)0.45690 (11)0.0924 (10)
O2BA0.5305 (6)0.4599 (7)0.4261 (2)0.1086 (19)0.80 (2)
O3BA0.5020 (6)0.5403 (14)0.3479 (3)0.126 (2)0.80 (2)
O2BB0.5629 (15)0.483 (4)0.43148 (19)0.1086 (19)0.20 (2)
O3BB0.493 (3)0.556 (6)0.3597 (9)0.126 (2)0.20 (2)
O4BA0.6720 (3)0.4105 (6)0.21067 (13)0.149 (3)0.950 (19)
O5BA0.8123 (3)0.4153 (7)0.22437 (14)0.136 (3)0.950 (19)
O4BB0.6771 (15)0.376 (6)0.2114 (4)0.149 (3)0.050 (19)
O5BB0.803 (2)0.470 (5)0.2232 (5)0.136 (3)0.050 (19)
O6BA0.9445 (3)0.3776 (7)0.4123 (2)0.114 (2)0.756 (8)
O7BA0.8773 (4)0.4852 (11)0.4686 (2)0.120 (2)0.756 (8)
O6BB0.9310 (8)0.461 (2)0.3901 (5)0.114 (2)0.244 (8)
O7BB0.8972 (14)0.478 (4)0.4700 (5)0.120 (2)0.244 (8)
N1B0.5528 (2)0.4924 (4)0.38306 (12)0.0794 (9)
N2B0.7398 (3)0.4172 (3)0.24045 (11)0.1022 (17)
N3B0.8814 (2)0.4406 (4)0.42404 (12)0.0837 (10)
C1B0.7204 (3)0.4642 (3)0.40885 (12)0.0632 (9)
C2B0.6469 (3)0.4639 (3)0.36980 (15)0.0606 (8)
C3B0.6514 (3)0.4471 (3)0.31648 (14)0.0619 (9)
H3BA0.59990.44720.29300.074*
C4B0.7305 (3)0.4302 (3)0.29740 (11)0.0612 (9)
C5B0.8079 (3)0.4290 (3)0.33118 (17)0.0669 (10)
H5BA0.86230.41720.31790.080*
C6B0.8022 (3)0.4458 (3)0.38576 (16)0.0669 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0331 (10)0.0443 (11)0.0259 (9)0.0034 (8)0.0041 (7)0.0004 (8)
N20.0504 (12)0.0432 (12)0.0302 (10)0.0019 (9)0.0047 (9)−0.0040 (9)
C10.0331 (12)0.0481 (14)0.0418 (13)0.0051 (10)0.0076 (10)−0.0005 (11)
C20.0414 (13)0.0484 (15)0.0393 (13)0.0070 (11)−0.0001 (10)0.0017 (11)
C30.0405 (13)0.0501 (15)0.0391 (13)−0.0047 (11)0.0063 (10)−0.0046 (11)
C40.0356 (12)0.0506 (14)0.0339 (12)0.0023 (11)0.0002 (9)−0.0012 (10)
C50.0480 (13)0.0452 (13)0.0225 (10)0.0037 (11)0.0057 (9)0.0033 (9)
C60.0417 (13)0.0409 (13)0.0349 (12)0.0006 (10)0.0003 (10)0.0013 (10)
C70.0501 (15)0.0670 (19)0.0396 (14)0.0057 (14)−0.0002 (11)0.0096 (13)
C80.0548 (18)0.077 (2)0.066 (2)0.0148 (17)−0.0096 (15)0.0207 (18)
C90.0429 (15)0.0615 (19)0.079 (2)0.0129 (14)−0.0023 (14)−0.0033 (16)
C100.0477 (16)0.068 (2)0.0591 (18)0.0118 (14)0.0060 (13)−0.0144 (15)
C110.0516 (15)0.0595 (17)0.0372 (14)0.0122 (13)0.0006 (11)−0.0033 (12)
C120.0407 (13)0.0485 (14)0.0395 (13)0.0050 (11)0.0096 (10)0.0054 (11)
C130.0509 (17)0.100 (3)0.0545 (19)−0.0023 (18)0.0131 (14)0.0241 (18)
C140.0514 (19)0.111 (4)0.102 (3)−0.015 (2)0.021 (2)0.041 (3)
C150.0446 (17)0.083 (3)0.113 (3)−0.0171 (17)−0.0048 (19)0.018 (2)
C160.0619 (19)0.070 (2)0.068 (2)−0.0113 (17)−0.0049 (16)−0.0060 (17)
C170.0530 (16)0.0623 (18)0.0419 (15)−0.0087 (14)0.0042 (12)0.0006 (13)
C18A0.079 (2)0.0422 (15)0.0474 (16)0.0015 (14)0.0080 (14)0.0001 (12)
C19A0.058 (3)0.049 (2)0.053 (2)0.000 (3)0.011 (3)0.0089 (18)
C20A0.060 (2)0.050 (2)0.047 (2)0.004 (2)0.012 (2)0.0043 (18)
C21A0.060 (7)0.039 (3)0.063 (5)0.003 (6)0.021 (5)0.004 (3)
C22A0.043 (6)0.059 (4)0.069 (7)0.000 (5)−0.011 (4)0.008 (5)
C23A0.062 (6)0.056 (8)0.078 (9)0.006 (5)−0.001 (5)−0.005 (7)
C24A0.115 (15)0.042 (6)0.046 (8)−0.021 (7)−0.001 (7)−0.003 (4)
C25A0.085 (12)0.065 (10)0.088 (14)−0.001 (7)0.021 (8)−0.023 (7)
C26A0.071 (11)0.050 (5)0.084 (10)−0.001 (7)−0.040 (9)−0.001 (5)
C18B0.079 (2)0.0422 (15)0.0474 (16)0.0015 (14)0.0080 (14)0.0001 (12)
C19B0.058 (3)0.049 (2)0.053 (2)0.000 (3)0.011 (3)0.0089 (18)
C20B0.060 (2)0.050 (2)0.047 (2)0.004 (2)0.012 (2)0.0043 (18)
C21B0.052 (8)0.041 (4)0.043 (5)0.003 (7)0.020 (5)0.003 (3)
C22B0.026 (7)0.067 (6)0.054 (8)0.002 (6)−0.017 (5)0.004 (6)
C23B0.13 (3)0.066 (16)0.11 (2)−0.007 (13)−0.018 (18)0.042 (15)
C24B0.11 (2)0.070 (12)0.030 (8)0.046 (11)0.019 (9)0.004 (6)
C25B0.080 (12)0.037 (7)0.037 (8)0.006 (7)0.019 (7)0.003 (6)
C26B0.064 (12)0.042 (5)0.042 (6)0.004 (8)−0.026 (8)−0.003 (4)
O1A0.111 (2)0.0770 (16)0.0255 (10)−0.0050 (14)0.0153 (11)0.0045 (10)
O2AA0.092 (5)0.157 (7)0.068 (2)0.028 (5)−0.035 (2)−0.036 (3)
O3AA0.036 (3)0.371 (16)0.098 (3)0.009 (6)−0.004 (3)−0.030 (7)
O2AB0.092 (5)0.157 (7)0.068 (2)0.028 (5)−0.035 (2)−0.036 (3)
O3AB0.036 (3)0.371 (16)0.098 (3)0.009 (6)−0.004 (3)−0.030 (7)
O4A0.112 (2)0.102 (2)0.0538 (15)−0.0046 (18)0.0436 (15)0.0099 (14)
O5A0.118 (2)0.095 (2)0.0289 (11)0.0025 (17)0.0035 (13)0.0106 (11)
O6AA0.062 (2)0.271 (8)0.068 (3)−0.027 (3)−0.0050 (18)0.040 (4)
O7AA0.090 (3)0.265 (9)0.083 (4)−0.038 (4)0.050 (3)−0.053 (5)
O6AB0.062 (2)0.271 (8)0.068 (3)−0.027 (3)−0.0050 (18)0.040 (4)
O7AB0.090 (3)0.265 (9)0.083 (4)−0.038 (4)0.050 (3)−0.053 (5)
N1A0.0604 (17)0.090 (2)0.0574 (17)0.0002 (16)−0.0077 (13)−0.0144 (15)
N2A0.096 (2)0.0496 (14)0.0352 (13)0.0009 (14)0.0206 (14)0.0022 (10)
N3A0.0589 (17)0.114 (3)0.0562 (17)−0.0070 (18)0.0158 (14)0.0052 (17)
C1A0.0646 (17)0.0379 (13)0.0272 (12)−0.0032 (12)0.0059 (11)−0.0032 (9)
C2A0.0566 (16)0.0450 (14)0.0361 (13)−0.0022 (12)−0.0001 (11)−0.0035 (11)
C3A0.0599 (17)0.0450 (14)0.0453 (15)−0.0080 (13)0.0163 (12)−0.0041 (12)
C4A0.0696 (18)0.0384 (13)0.0291 (13)−0.0002 (12)0.0115 (11)0.0030 (10)
C5A0.0610 (17)0.0491 (15)0.0330 (13)0.0019 (13)0.0029 (11)0.0031 (11)
C6A0.0553 (16)0.0532 (16)0.0349 (13)−0.0051 (13)0.0101 (11)−0.0004 (11)
O1B0.0833 (19)0.145 (3)0.0486 (14)−0.0058 (19)0.0058 (12)−0.0186 (16)
O2BA0.047 (4)0.159 (5)0.123 (3)−0.007 (3)0.023 (2)0.013 (3)
O3BA0.083 (3)0.166 (6)0.126 (4)0.036 (3)−0.002 (3)0.028 (5)
O2BB0.047 (4)0.159 (5)0.123 (3)−0.007 (3)0.023 (2)0.013 (3)
O3BB0.083 (3)0.166 (6)0.126 (4)0.036 (3)−0.002 (3)0.028 (5)
O4BA0.321 (8)0.073 (3)0.0417 (16)0.015 (3)−0.037 (3)−0.0044 (15)
O5BA0.267 (6)0.079 (4)0.081 (2)0.013 (3)0.109 (4)0.0066 (18)
O4BB0.321 (8)0.073 (3)0.0417 (16)0.015 (3)−0.037 (3)−0.0044 (15)
O5BB0.267 (6)0.079 (4)0.081 (2)0.013 (3)0.109 (4)0.0066 (18)
O6BA0.060 (2)0.199 (7)0.083 (3)0.038 (3)0.002 (2)−0.019 (3)
O7BA0.069 (4)0.198 (5)0.087 (2)0.029 (4)−0.015 (2)−0.044 (3)
O6BB0.060 (2)0.199 (7)0.083 (3)0.038 (3)0.002 (2)−0.019 (3)
O7BB0.069 (4)0.198 (5)0.087 (2)0.029 (4)−0.015 (2)−0.044 (3)
N1B0.086 (2)0.075 (2)0.077 (2)−0.0108 (18)0.0077 (19)0.0077 (17)
N2B0.219 (6)0.0467 (17)0.0441 (18)0.013 (2)0.030 (3)0.0043 (14)
N3B0.068 (2)0.104 (3)0.079 (2)−0.0047 (19)0.0071 (17)−0.016 (2)
C1B0.106 (3)0.0482 (16)0.0361 (15)−0.0035 (17)0.0081 (16)−0.0068 (12)
C2B0.078 (2)0.0448 (16)0.0622 (19)−0.0044 (15)0.0237 (17)−0.0017 (14)
C3B0.085 (2)0.0398 (15)0.0569 (19)−0.0046 (15)−0.0138 (17)−0.0028 (13)
C4B0.115 (3)0.0375 (14)0.0333 (14)0.0022 (16)0.0168 (16)0.0006 (11)
C5B0.077 (2)0.0393 (15)0.089 (3)0.0016 (15)0.031 (2)0.0018 (16)
C6B0.077 (2)0.0464 (16)0.072 (2)−0.0066 (16)−0.0183 (18)0.0004 (15)
Geometric parameters (Å, º) top
N1—C41.505 (3)C19B—C20B1.309 (12)
N1—C11.505 (3)C19B—H19B0.9300
N1—C51.522 (3)C20B—C21B1.493 (9)
N1—H1N0.901 (5)C20B—H20B0.9300
N2—C21.488 (4)C21B—C26B1.30 (4)
N2—C31.490 (4)C21B—C22B1.385 (14)
N2—C18A1.524 (4)C22B—C23B1.47 (5)
N2—H2N0.897 (5)C22B—H22B0.9300
C1—C21.514 (4)C23B—C24B1.35 (5)
C1—H1A0.9700C23B—H23B0.9300
C1—H1B0.9700C24B—C25B1.40 (6)
C2—H2A0.9700C24B—H24B0.9300
C2—H2B0.9700C25B—C26B1.39 (4)
C3—C41.515 (4)C25B—H25B0.9300
C3—H3A0.9700C26B—H26B0.9300
C3—H3B0.9700O1A—C1A1.241 (3)
C4—H4A0.9700O2AA—N1A1.2115 (16)
C4—H4B0.9700O3AA—N1A1.2120 (17)
C5—C61.513 (4)O2AB—N1A1.2115 (17)
C5—C121.513 (4)O3AB—N1A1.2118 (17)
C5—H5A0.9800O4A—N2A1.2118 (16)
C6—C71.382 (4)O5A—N2A1.2125 (16)
C6—C111.389 (4)O6AA—N3A1.2122 (16)
C7—C81.381 (5)O7AA—N3A1.2115 (16)
C7—H7A0.9300O6AB—N3A1.2117 (17)
C8—C91.367 (6)O7AB—N3A1.2117 (17)
C8—H8A0.9300N1A—C2A1.461 (4)
C9—C101.375 (5)N2A—C4A1.446 (3)
C9—H9A0.9300N3A—C6A1.433 (4)
C10—C111.378 (4)C1A—C2A1.432 (4)
C10—H10A0.9300C1A—C6A1.443 (4)
C11—H11A0.9300C2A—C3A1.388 (4)
C12—C131.388 (4)C3A—C4A1.370 (4)
C12—C171.394 (4)C3A—H3AA0.9300
C13—C141.386 (6)C4A—C5A1.377 (4)
C13—H13A0.9300C5A—C6A1.371 (4)
C14—C151.371 (7)C5A—H5AA0.9300
C14—H14A0.9300O1B—C1B1.259 (4)
C15—C161.374 (6)O2BA—N1B1.2101 (17)
C15—H15A0.9300O3BA—N1B1.2111 (17)
C16—C171.380 (5)O2BB—N1B1.2118 (17)
C16—H16A0.9300O3BB—N1B1.2116 (17)
C17—H17A0.9300O4BA—N2B1.2109 (16)
C18A—C19A1.546 (7)O5BA—N2B1.2120 (16)
C18A—H18A0.9700O4BB—N2B1.2119 (17)
C18A—H18B0.9700O5BB—N2B1.2119 (17)
C19A—C20A1.310 (9)O6BA—N3B1.2132 (16)
C19A—H19A0.9300O7BA—N3B1.2120 (16)
C20A—C21A1.483 (8)O6BB—N3B1.2116 (17)
C20A—H20A0.9300O7BB—N3B1.2117 (17)
C21A—C22A1.382 (12)N1B—C2B1.528 (5)
C21A—C26A1.46 (3)N2B—C4B1.455 (4)
C22A—C23A1.29 (3)N3B—C6B1.461 (5)
C22A—H22A0.9300C1B—C2B1.407 (6)
C23A—C24A1.33 (3)C1B—C6B1.437 (6)
C23A—H23A0.9300C2B—C3B1.356 (5)
C24A—C25A1.36 (5)C3B—C4B1.350 (6)
C24A—H24A0.9300C3B—H3BA0.9300
C25A—C26A1.42 (4)C4B—C5B1.376 (6)
C25A—H25A0.9300C5B—C6B1.390 (6)
C26A—H26A0.9300C5B—H5BA0.9300
Cg1···Cg33.844 (7)Cg2···Cg43.634 (2)
Cg1···Cg43.677 (9)Cg3···Cg4i3.729 (7)
Cg2···Cg33.825 (5)
C4—N1—C1108.3 (2)C25A—C26A—C21A127.5 (18)
C4—N1—C5111.38 (19)C25A—C26A—H26A116.3
C1—N1—C5110.63 (19)C21A—C26A—H26A116.3
C4—N1—H1N107 (2)C20B—C19B—H19B120.2
C1—N1—H1N107 (2)C19B—C20B—C21B124.0 (9)
C5—N1—H1N113 (2)C19B—C20B—H20B118.0
C2—N2—C3110.4 (2)C21B—C20B—H20B118.0
C2—N2—C18A112.0 (2)C26B—C21B—C22B121.5 (13)
C3—N2—C18A111.5 (2)C26B—C21B—C20B110.3 (13)
C2—N2—H2N103 (3)C22B—C21B—C20B128.1 (12)
C3—N2—H2N114 (3)C21B—C22B—C23B120 (2)
C18A—N2—H2N106 (3)C21B—C22B—H22B120.2
N1—C1—C2110.7 (2)C23B—C22B—H22B120.3
N1—C1—H1A109.5C24B—C23B—C22B123 (4)
C2—C1—H1A109.5C24B—C23B—H23B118.5
N1—C1—H1B109.5C22B—C23B—H23B118.5
C2—C1—H1B109.5C23B—C24B—C25B108 (3)
H1A—C1—H1B108.1C23B—C24B—H24B126.1
N2—C2—C1111.4 (2)C25B—C24B—H24B126.1
N2—C2—H2A109.3C26B—C25B—C24B134 (3)
C1—C2—H2A109.3C26B—C25B—H25B113.1
N2—C2—H2B109.3C24B—C25B—H25B113.1
C1—C2—H2B109.3C21B—C26B—C25B114 (2)
H2A—C2—H2B108.0C21B—C26B—H26B123.1
N2—C3—C4111.1 (2)C25B—C26B—H26B123.1
N2—C3—H3A109.4O2AB—N1A—O3AB122.6 (2)
C4—C3—H3A109.4O2AA—N1A—O3AB120.6 (19)
N2—C3—H3B109.4O2AB—N1A—O3AA111.7 (16)
C4—C3—H3B109.4O2AA—N1A—O3AA122.6 (2)
H3A—C3—H3B108.0O2AB—N1A—C2A125.8 (12)
N1—C4—C3110.8 (2)O2AA—N1A—C2A117.5 (5)
N1—C4—H4A109.5O3AB—N1A—C2A109.6 (10)
C3—C4—H4A109.5O3AA—N1A—C2A119.9 (5)
N1—C4—H4B109.5O4A—N2A—O5A122.6 (2)
C3—C4—H4B109.5O4A—N2A—C4A118.4 (2)
H4A—C4—H4B108.1O5A—N2A—C4A119.0 (2)
C6—C5—C12110.6 (2)O7AA—N3A—O6AB106.6 (14)
C6—C5—N1112.2 (2)O7AB—N3A—O6AB122.6 (2)
C12—C5—N1112.0 (2)O7AA—N3A—O6AA122.6 (2)
C6—C5—H5A107.2O7AB—N3A—O6AA114 (2)
C12—C5—H5A107.2O7AA—N3A—C6A120.1 (3)
N1—C5—H5A107.2O7AB—N3A—C6A116.2 (13)
C7—C6—C11118.3 (3)O6AB—N3A—C6A121.2 (13)
C7—C6—C5119.1 (2)O6AA—N3A—C6A117.4 (3)
C11—C6—C5122.3 (2)O1A—C1A—C2A124.6 (3)
C8—C7—C6120.8 (3)O1A—C1A—C6A123.3 (3)
C8—C7—H7A119.6C2A—C1A—C6A112.1 (2)
C6—C7—H7A119.6C3A—C2A—C1A124.4 (3)
C9—C8—C7120.2 (3)C3A—C2A—N1A116.3 (3)
C9—C8—H8A119.9C1A—C2A—N1A119.3 (2)
C7—C8—H8A119.9C4A—C3A—C2A118.7 (3)
C8—C9—C10119.7 (3)C4A—C3A—H3AA120.7
C8—C9—H9A120.1C2A—C3A—H3AA120.7
C10—C9—H9A120.1C3A—C4A—C5A121.4 (2)
C9—C10—C11120.4 (3)C3A—C4A—N2A120.2 (3)
C9—C10—H10A119.8C5A—C4A—N2A118.4 (3)
C11—C10—H10A119.8C6A—C5A—C4A119.4 (3)
C10—C11—C6120.5 (3)C6A—C5A—H5AA120.3
C10—C11—H11A119.8C4A—C5A—H5AA120.3
C6—C11—H11A119.8C5A—C6A—N3A116.3 (3)
C13—C12—C17117.9 (3)C5A—C6A—C1A124.0 (3)
C13—C12—C5119.1 (3)N3A—C6A—C1A119.7 (2)
C17—C12—C5122.8 (2)O2BA—N1B—O3BA122.8 (2)
C14—C13—C12120.9 (4)O2BA—N1B—O3BB108.0 (17)
C14—C13—H13A119.5O3BA—N1B—O2BB140.1 (12)
C12—C13—H13A119.5O3BB—N1B—O2BB122.6 (2)
C15—C14—C13120.3 (3)O2BA—N1B—C2B119.9 (4)
C15—C14—H14A119.8O3BA—N1B—C2B117.2 (5)
C13—C14—H14A119.8O3BB—N1B—C2B131.8 (18)
C14—C15—C16119.5 (4)O2BB—N1B—C2B100.3 (10)
C14—C15—H15A120.2O4BA—N2B—O5BB117.3 (15)
C16—C15—H15A120.2O4BB—N2B—O5BB122.6 (2)
C15—C16—C17120.7 (4)O4BA—N2B—O5BA122.6 (2)
C15—C16—H16A119.6O4BB—N2B—O5BA118.7 (11)
C17—C16—H16A119.6O4BA—N2B—C4B116.6 (3)
C16—C17—C12120.6 (3)O4BB—N2B—C4B118.0 (3)
C16—C17—H17A119.7O5BB—N2B—C4B118.0 (3)
C12—C17—H17A119.7O5BA—N2B—C4B120.7 (3)
N2—C18A—C19A112.8 (3)O6BB—N3B—O7BB122.6 (3)
N2—C18A—H18A109.0O6BB—N3B—O7BA132.8 (12)
C19A—C18A—H18A109.0O7BB—N3B—O6BA107.9 (17)
N2—C18A—H18B109.0O7BA—N3B—O6BA122.4 (2)
C19A—C18A—H18B109.0O6BB—N3B—C6B93.6 (8)
H18A—C18A—H18B107.8O7BB—N3B—C6B133.1 (15)
C20A—C19A—C18A121.1 (5)O7BA—N3B—C6B118.4 (3)
C20A—C19A—H19A119.4O6BA—N3B—C6B118.6 (3)
C18A—C19A—H19A119.4O1B—C1B—C2B117.7 (4)
C19A—C20A—C21A129.3 (7)O1B—C1B—C6B130.2 (4)
C19A—C20A—H20A115.4C2B—C1B—C6B112.1 (3)
C21A—C20A—H20A115.4C3B—C2B—C1B124.7 (4)
C22A—C21A—C26A114.1 (13)C3B—C2B—N1B112.4 (3)
C22A—C21A—C20A121.5 (10)C1B—C2B—N1B122.8 (3)
C26A—C21A—C20A124.4 (14)C4B—C3B—C2B120.1 (3)
C23A—C22A—C21A119.1 (14)C4B—C3B—H3BA119.9
C23A—C22A—H22A120.4C2B—C3B—H3BA119.9
C21A—C22A—H22A120.4C3B—C4B—C5B121.2 (3)
C22A—C23A—C24A124 (2)C3B—C4B—N2B122.6 (4)
C22A—C23A—H23A117.9C5B—C4B—N2B116.1 (4)
C24A—C23A—H23A117.9C4B—C5B—C6B118.0 (3)
C23A—C24A—C25A128 (2)C4B—C5B—H5BA121.0
C23A—C24A—H24A115.9C6B—C5B—H5BA121.0
C25A—C24A—H24A115.9C5B—C6B—C1B123.8 (3)
C24A—C25A—C26A106 (2)C5B—C6B—N3B120.8 (4)
C24A—C25A—H25A126.8C1B—C6B—N3B115.4 (3)
C26A—C25A—H25A126.8
C4—N1—C1—C2−58.5 (3)O3AA—N1A—C2A—C3A14.3 (14)
C5—N1—C1—C2179.1 (2)O2AB—N1A—C2A—C1A37 (2)
C3—N2—C2—C1−55.7 (3)O2AA—N1A—C2A—C1A15.2 (9)
C18A—N2—C2—C1179.5 (2)O3AB—N1A—C2A—C1A−127.4 (18)
N1—C1—C2—N258.0 (3)O3AA—N1A—C2A—C1A−163.3 (13)
C2—N2—C3—C455.7 (3)C1A—C2A—C3A—C4A−0.9 (4)
C18A—N2—C3—C4−179.2 (2)N1A—C2A—C3A—C4A−178.3 (3)
C1—N1—C4—C358.8 (3)C2A—C3A—C4A—C5A0.4 (4)
C5—N1—C4—C3−179.36 (19)C2A—C3A—C4A—N2A179.5 (3)
N2—C3—C4—N1−58.3 (3)O4A—N2A—C4A—C3A4.0 (4)
C4—N1—C5—C654.6 (3)O5A—N2A—C4A—C3A−176.3 (3)
C1—N1—C5—C6175.1 (2)O4A—N2A—C4A—C5A−176.9 (3)
C4—N1—C5—C12179.7 (2)O5A—N2A—C4A—C5A2.8 (4)
C1—N1—C5—C12−59.8 (3)C3A—C4A—C5A—C6A−0.5 (5)
C12—C5—C6—C7104.0 (3)N2A—C4A—C5A—C6A−179.6 (3)
N1—C5—C6—C7−130.2 (3)C4A—C5A—C6A—N3A179.0 (3)
C12—C5—C6—C11−70.3 (3)C4A—C5A—C6A—C1A1.1 (5)
N1—C5—C6—C1155.6 (3)O7AA—N3A—C6A—C5A160.3 (7)
C11—C6—C7—C81.6 (5)O7AB—N3A—C6A—C5A119 (3)
C5—C6—C7—C8−172.9 (3)O6AB—N3A—C6A—C5A−62 (2)
C6—C7—C8—C9−0.7 (6)O6AA—N3A—C6A—C5A−20.9 (7)
C7—C8—C9—C10−1.4 (6)O7AA—N3A—C6A—C1A−21.7 (8)
C8—C9—C10—C112.6 (6)O7AB—N3A—C6A—C1A−63 (3)
C9—C10—C11—C6−1.6 (5)O6AB—N3A—C6A—C1A116 (2)
C7—C6—C11—C10−0.4 (5)O6AA—N3A—C6A—C1A157.1 (6)
C5—C6—C11—C10173.9 (3)O1A—C1A—C6A—C5A176.1 (3)
C6—C5—C12—C13−95.4 (3)C2A—C1A—C6A—C5A−1.4 (4)
N1—C5—C12—C13138.6 (3)O1A—C1A—C6A—N3A−1.7 (5)
C6—C5—C12—C1778.4 (3)C2A—C1A—C6A—N3A−179.3 (3)
N1—C5—C12—C17−47.6 (3)O1B—C1B—C2B—C3B179.4 (4)
C17—C12—C13—C14−1.2 (5)C6B—C1B—C2B—C3B0.6 (5)
C5—C12—C13—C14172.9 (4)O1B—C1B—C2B—N1B3.7 (5)
C12—C13—C14—C151.7 (7)C6B—C1B—C2B—N1B−175.1 (3)
C13—C14—C15—C16−0.4 (7)O2BA—N1B—C2B—C3B151.3 (6)
C14—C15—C16—C17−1.3 (7)O3BA—N1B—C2B—C3B−24.4 (10)
C15—C16—C17—C121.7 (6)O3BB—N1B—C2B—C3B−37 (4)
C13—C12—C17—C16−0.5 (5)O2BB—N1B—C2B—C3B169.8 (18)
C5—C12—C17—C16−174.3 (3)O2BA—N1B—C2B—C1B−32.6 (7)
C2—N2—C18A—C19A74.9 (4)O3BA—N1B—C2B—C1B151.8 (9)
C3—N2—C18A—C19A−49.4 (4)O3BB—N1B—C2B—C1B139 (4)
N2—C18A—C19A—C20A−100.0 (5)O2BB—N1B—C2B—C1B−14.1 (19)
C18A—C19A—C20A—C21A−178.2 (7)C1B—C2B—C3B—C4B−0.6 (5)
C19A—C20A—C21A—C22A−176.6 (8)N1B—C2B—C3B—C4B175.5 (3)
C19A—C20A—C21A—C26A4 (2)C2B—C3B—C4B—C5B0.3 (5)
C26A—C21A—C22A—C23A2 (2)C2B—C3B—C4B—N2B−177.4 (3)
C20A—C21A—C22A—C23A−177.1 (14)O4BA—N2B—C4B—C3B−6.4 (6)
C21A—C22A—C23A—C24A1 (3)O4BB—N2B—C4B—C3B−25 (3)
C22A—C23A—C24A—C25A−7 (3)O5BB—N2B—C4B—C3B142 (3)
C23A—C24A—C25A—C26A8 (3)O5BA—N2B—C4B—C3B172.7 (5)
C24A—C25A—C26A—C21A−5 (4)O4BA—N2B—C4B—C5B175.9 (4)
C22A—C21A—C26A—C25A1 (3)O4BB—N2B—C4B—C5B157 (3)
C20A—C21A—C26A—C25A180 (2)O5BB—N2B—C4B—C5B−36 (3)
C19B—C20B—C21B—C26B178.7 (18)O5BA—N2B—C4B—C5B−5.1 (6)
C19B—C20B—C21B—C22B−5 (2)C3B—C4B—C5B—C6B−0.1 (5)
C26B—C21B—C22B—C23B−2 (3)N2B—C4B—C5B—C6B177.7 (3)
C20B—C21B—C22B—C23B−178 (2)C4B—C5B—C6B—C1B0.1 (5)
C21B—C22B—C23B—C24B0 (4)C4B—C5B—C6B—N3B177.7 (3)
C22B—C23B—C24B—C25B4 (4)O1B—C1B—C6B—C5B−178.9 (4)
C23B—C24B—C25B—C26B−8 (5)C2B—C1B—C6B—C5B−0.3 (5)
C22B—C21B—C26B—C25B−1 (4)O1B—C1B—C6B—N3B3.4 (6)
C20B—C21B—C26B—C25B175 (2)C2B—C1B—C6B—N3B−178.0 (3)
C24B—C25B—C26B—C21B7 (5)O6BB—N3B—C6B—C5B19.3 (11)
O1A—C1A—C2A—C3A−176.2 (3)O7BB—N3B—C6B—C5B162 (2)
C6A—C1A—C2A—C3A1.3 (4)O7BA—N3B—C6B—C5B163.2 (7)
O1A—C1A—C2A—N1A1.1 (5)O6BA—N3B—C6B—C5B−25.8 (7)
C6A—C1A—C2A—N1A178.6 (3)O6BB—N3B—C6B—C1B−162.9 (11)
O2AB—N1A—C2A—C3A−146 (2)O7BB—N3B—C6B—C1B−20 (2)
O2AA—N1A—C2A—C3A−167.3 (8)O7BA—N3B—C6B—C1B−19.0 (9)
O3AB—N1A—C2A—C3A50.1 (18)O6BA—N3B—C6B—C1B152.0 (5)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
Cg5 and Cg6 are the centroids of the C6–C11 and C12–C17 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1A0.90 (1)1.77 (1)2.658 (3)168 (3)
N2—H2N···O1B0.90 (1)1.83 (3)2.603 (3)143 (4)
N2—H2N···O7BA0.90 (1)2.30 (3)3.047 (5)140 (3)
C3—H3A···O2AA0.972.503.214 (8)130
C3—H3A···O2AB0.972.523.242 (17)131
C2—H2B···O7AA0.972.483.304 (5)142
C2—H2B···O7AB0.972.543.42 (4)151
C11—H11A···O4BAii0.932.573.244 (4)130
C17—H17A···O1A0.932.623.473 (4)154
C17—H17A···O5BBii0.932.523.267 (8)138
C18A—H18A···Cg6i0.972.883.742 (5)148
C18A—H18B···Cg5i0.972.833.762 (1)161
C18A—H18C···Cg5i0.973.003.762 (1)137
C18A—H18D···Cg6i0.972.843.742 (5)155
Symmetry codes: (i) x, y+1, z; (ii) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC26H30N22+·2C6H2N3O7−
Mr826.73
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)15.1987 (2), 10.09130 (17), 25.0724 (3)
β (°) 95.9170 (14)
V (Å3)3824.98 (10)
Z4
Radiation typeCu Kα
µ (mm−1)0.95
Crystal size (mm)0.49 × 0.42 × 0.27
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby Gemini
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.777, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		14786, 7319, 5784
Rint0.024
(sin θ/λ)max (Å−1)0.622
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.092, 0.289, 1.01
No. of reflections7319
No. of parameters648
No. of restraints40
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)1.24, −0.48

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg5 and Cg6 are the centroids of the C6–C11 and C12–C17 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1A0.901 (5)1.770 (9)2.658 (3)168 (3)
N2—H2N···O1B0.897 (5)1.83 (3)2.603 (3)143 (4)
N2—H2N···O7BA0.897 (5)2.30 (3)3.047 (5)140 (3)
C3—H3A···O2AA0.972.503.214 (8)130
C3—H3A···O2AB0.972.523.242 (17)131
C2—H2B···O7AA0.972.483.304 (5)142
C2—H2B···O7AB0.972.543.42 (4)151
C11—H11A···O4BAi0.932.573.244 (4)130
C17—H17A···O1A0.932.623.473 (4)154
C17—H17A···O5BBi0.932.523.267 (8)138
C18A—H18A···Cg6ii0.972.883.742 (5)148
C18A—H18B···Cg5ii0.972.833.762 (0)161
C18A—H18C···Cg5ii0.973.003.762 (0)137
C18A—H18D···Cg6ii0.972.843.742 (5)155
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y+1, z.
 

Acknowledgements

MSS thanks the University of Mysore for the research facilities and HSY thanks the UOM for a sabbatical leave. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
 First citationBarrett, R. J. & Zolov, B. (1960). J. Maine Med. Assoc. 51, 454–457.  PubMed Google Scholar
 First citationBertolasi, V., Borea, P. A., Gilli, G. & Sacerdoti, M. (1980). Acta Cryst. B36, 1975–1977.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
 First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem, Soc. 97, 1354–1358.  Google Scholar
 First citationJasinski, J. P., Pek, A. E., Siddaraju, B. P., Yathirajan, H. S. & Narayana, B. (2010). Acta Cryst. E66, o1979–o1980.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationMouillé, Y., Cotrait, M., Hospital, M. & Marsau, P. (1975). Acta Cryst. B31, 1495–1496.  CSD CrossRef IUCr Journals Web of Science Google Scholar
 First citationOxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationTowse, G. (1980). J. Laryngol. Otol. 94, 1009–1015.  CrossRef CAS PubMed Web of Science 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 67| Part 2| February 2011| Pages o500-o501
doi:10.1107/S1600536811002674
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS