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Acta Cryst. (2011). E67, o190-o191    [ doi:10.1107/S1600536810049937 ]

Orphenadrinium picrate

J. P. Jasinski, R. J. Butcher, B. P. Siddaraju, H. S. Yathirajan and B. Narayana

Abstract top

In the title molecular salt {systematic name: N,N-dimethyl-2-[(2-methylphenyl)(phenyl)methoxy]ethanaminium 2,4,6-trinitrophenolate}, C18H24NO+·C6H2N3O7-, the phenyl rings of the orphenadrinum cation are disordered [occupancies = 0.662 (4) and 0.338 (4)]. The N atom in the orphenadrinum cation is protonated. The picrate anion interacts with the protonated N atom through a bifurcated N-H...O hydrogen bond, forming an R12(6) ring motif with an adjacent cation. The mean planes of the two o-NO2 and single p-NO2 groups in the picrate anion are twisted by 23.0 (6), 31.3 (3) and 6.3 (2)° with respect to the mean planes of the six-membered ring. Weak intermolecular C-H...O hydrogen bonds, C-H...[pi] intermolecular interactions and weak [pi]-[pi] stacking interactions [centroid-centroid distances = 3.677 (2) and 3.515 (3) Å} stabilize the crystal packing, creating a three-dimensional network.

Comment top

Orphenadrine (systematic IUPAC name: N, N-dimethyl-2-[(2-methylphenyl) phenyl-methoxy]ethanamine) is an anticholinergic drug of the ethanolamine antihistamine class with prominent CNS and peripheral actions used to treat painful muscle spasm and other symptoms and conditions as well as some aspects of Parkinson's disease. It is closely related to diphenhydramine and therefore related to other drugs used for Parkinson's like benztropine and trihexyphenidyl and is also structurally related to nefopam, a centrally acting yet non-opioid analgesic. Clinical and pharmacological review of the efficacy of orphenadrine and its combination with paracetamol has been described (Hunskaar & Donnel, 1991).

The solid-state structure of orphenadrine hydrochloride and conformational comparisons with diphenhydramine hydrochloride and nefopam hydrochloride was reported (Glaser et al., 1992). The crystal structure of orphenadrinium picrate picric acid is recently reported (Fun et al., 2010). The present work reports the crystal structure of the title compound, (I), which was obtained by the interaction between orphenadrine hydrochloride and 2,4,6-trinitrophenol in aqueous medium.

In the crystal structure of the title compound, C18H24NO+. C6H2N3O7-, there is one cation-anion pair in the asymmetric unit (Fig. 1). The two phenyl rings in the orphenadrinum cation are disordered [occupancy C1A–C14A = 0.662 (4); C1C–C13C = 0.338 (4)] with a protonated N atom in the N-dimethylethanamine group (Fig. 2). The dihedral angle between the mean planes of the two cation phenyl rings [occupancy C1A–C14A = 0.662 (4)] is 73.2 (1)°. The picrate anion interacts with the protonated N atom through a bifurcated N—H···O hydrogen bond forming a R12(6) ring motif with an adjacent cation. The dihedral angle between the mean planes of the anion benzene and two cation phenyl rings [occupancy C1A–C14A = 0.662 (4)] is 77.2 (6)° and 9.7 (0)°, respectively. The mean planes of the two o-NO2 and single p-NO2 groups in the picrate anion are twisted by 23.0 (6)°, 31.3 (3)° and 6.3 (2)° with respect to the mean planes of the 6-membered benzene ring. Weak Intermolecular C—H···O hydrogen bonds, C—H···Cg intermolecular interactions (Table 1), and weak π–π stacking interactions (Table 2) dominate the crystal packing creating a 3-D supramolecular structure (Fig. 3).

Related literature top

For the pharmacological activity of the title compound, see: Hunskaar & Donnel (1991). For related structures, see: Fun et al. (2010); Glaser et al. (1992).

Experimental top

Orphenadrine hydrochloride (3.05 g, 0.01 mol) was dissolved in 25 ml of water and picric acid (2.4 g, 0.01 mol) was also dissolved in 25 ml of water. Both solutions were mixed and stirred in a beaker at room temperature for 1 h. The mixture was warmed at 323 K for 10 min & kept aside for 2 days at room temperature. The formed product was filtered and dried in vaccum desiccator over phosphorous pentoxide. The product was recrystallized from dimethyl sulphoxide by slow evaporation (m.p. 341–344 K).

Refinement top

The two o-phenyl rings in the orphenadrinium cation are disordered [occupancy C1A–C14A = 0.662 (4); C1C–C13C = 0.338 (4)]. All of the H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.95Å (CH), 0.96 & 0.99Å (CH2), 0.98Å (CH3) or 0.93Å (NH). Isotropic displacement parameters for these atoms were set to 1.19 times (NH), 1.19–1.21 (CH, CH2) or 1.49–1.50 (CH3) times Ueq of the parent atom.

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, (I), showing the atom labeling scheme and 50% probability displacement ellipsoids. Only the highest occupied atoms in the disordered phenyl rings [occupancy C1A–C14A = 0.662 (4)] are shown. Dashed lines indicate weak C—H···O intermolecular hydrogen bonds between the cation and anion and R12(6) ring motifs.
[Figure 2] Fig. 2. Molecular structure of the title compound, (I), showing the disordered atoms in the two phenyl rings [occupancy C1A–C14A = 0.662 (4); C1C–C13C = 0.338 (4)] of the orphenadrinium cation.
[Figure 3] Fig. 3. Packing diagram of the title compound viewed down the a axis. Only the highest occupied atoms in the disordered phenyl rings [occupancy C1A–C14A = 0.662 (4)] are shown. Dashed lines indicate weak intermolecular C—H···O hydrogen bond interactions creating a 3-D supramolecular structure.
N,N-dimethyl-2-[(2-methylphenyl)(phenyl)methoxy]ethanaminium 2,4,6-trinitrophenolate top
Crystal data top
C18H24NO+·C6H2N3O7−Z = 2
Mr = 498.49F(000) = 524
Triclinic, P1Dx = 1.372 Mg m−3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54184 Å
a = 9.9434 (10) ÅCell parameters from 3744 reflections
b = 11.2216 (8) Åθ = 4.6–74.4°
c = 11.3523 (12) ŵ = 0.88 mm−1
α = 78.658 (7)°T = 123 K
β = 76.342 (9)°Triangular plate, yellow
γ = 87.660 (7)°0.52 × 0.43 × 0.16 mm
V = 1206.82 (19) Å3
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		4677 independent reflections
Radiation source: Enhance (Cu) X-ray Source3760 reflections with I > 2σ(I)
graphiteRint = 0.031
Detector resolution: 10.5081 pixels mm-1θmax = 74.6°, θmin = 4.6°
ω scansh = −12→12
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		k = −13→13
Tmin = 0.635, Tmax = 1.000l = −8→14
7402 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)] = 0.065H-atom parameters constrained
wR(F2) = 0.188 w = 1/[σ2(Fo2) + (0.093P)2 + 0.5659P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
4677 reflectionsΔρmax = 0.45 e Å−3
407 parametersΔρmin = −0.40 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0038 (11)
Crystal data top
C18H24NO+·C6H2N3O7−γ = 87.660 (7)°
Mr = 498.49V = 1206.82 (19) Å3
Triclinic, P1Z = 2
a = 9.9434 (10) ÅCu Kα radiation
b = 11.2216 (8) ŵ = 0.88 mm−1
c = 11.3523 (12) ÅT = 123 K
α = 78.658 (7)°0.52 × 0.43 × 0.16 mm
β = 76.342 (9)°
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		4677 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		3760 reflections with I > 2σ(I)
Tmin = 0.635, Tmax = 1.000Rint = 0.031
7402 measured reflectionsθmax = 74.6°
Refinement top
R[F2 > 2σ(F2)] = 0.065H-atom parameters constrained
wR(F2) = 0.188Δρmax = 0.45 e Å−3
S = 1.09Δρmin = −0.40 e Å−3
4677 reflectionsAbsolute structure: ?
407 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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)
O1A0.7336 (3)0.61869 (16)0.6143 (2)0.0829 (7)
N1A0.7148 (2)0.35671 (16)0.72631 (17)0.0460 (5)
H1AB0.75690.41480.75410.055*
C1A0.6397 (4)0.7080 (3)0.6259 (3)0.0453 (9)0.662 (4)
H1AA0.54860.66830.66950.054*0.662 (4)
C2A0.6208 (5)0.7849 (4)0.5018 (4)0.051 (2)0.662 (4)
C3A0.7346 (4)0.8060 (4)0.4020 (6)0.0592 (16)0.662 (4)
H3AA0.82100.76960.40900.071*0.662 (4)
C4A0.7220 (4)0.8805 (3)0.2918 (4)0.0681 (13)0.662 (4)
H4AA0.79980.89490.22360.082*0.662 (4)
C5A0.5956 (6)0.9339 (3)0.2815 (3)0.0590 (14)0.662 (4)
H5AA0.58700.98480.20620.071*0.662 (4)
C6A0.4818 (4)0.9128 (4)0.3813 (5)0.0531 (17)0.662 (4)
H6AA0.39540.94930.37430.064*0.662 (4)
C7A0.4944 (4)0.8383 (3)0.4915 (4)0.0464 (11)0.662 (4)
C8A0.3672 (4)0.8167 (3)0.5954 (4)0.0581 (11)0.662 (4)
H8AA0.29090.86070.56980.087*0.662 (4)
H8AB0.34540.73150.61770.087*0.662 (4)
H8AC0.38420.84450.66540.087*0.662 (4)
C9A0.6762 (5)0.7860 (3)0.7096 (4)0.0536 (11)0.662 (4)
C10A0.5891 (5)0.7873 (3)0.8248 (4)0.0708 (15)0.662 (4)
H10A0.50690.73960.85120.085*0.662 (4)
C11A0.6224 (6)0.8585 (4)0.9013 (3)0.087 (2)0.662 (4)
H11A0.56290.85940.98010.104*0.662 (4)
C12A0.7428 (6)0.9283 (4)0.8627 (4)0.075 (3)0.662 (4)
H12A0.76560.97690.91500.091*0.662 (4)
C13A0.8299 (5)0.9269 (4)0.7475 (5)0.081 (2)0.662 (4)
H13A0.91210.97470.72100.097*0.662 (4)
C14A0.7966 (4)0.8558 (4)0.6709 (4)0.0721 (18)0.662 (4)
H14A0.85610.85490.59220.087*0.662 (4)
C15A0.7104 (3)0.5276 (2)0.5497 (2)0.0519 (6)
H15A0.80020.49970.50490.062*
H15B0.65620.56210.48840.062*
C16A0.6334 (3)0.4220 (2)0.6388 (2)0.0473 (5)
H16A0.54640.45170.68670.057*
H16B0.60850.36420.59170.057*
C17A0.6223 (3)0.2806 (2)0.8360 (2)0.0589 (7)
H17A0.55850.33320.88220.088*
H17B0.67850.23450.88950.088*
H17C0.56940.22410.80840.088*
C18A0.8262 (3)0.2799 (2)0.6658 (2)0.0598 (7)
H18A0.88460.33000.59250.090*
H18B0.78410.21400.64140.090*
H18C0.88280.24540.72400.090*
C1C0.7475 (7)0.7270 (6)0.5766 (6)0.0435 (16)0.338 (4)
H1CA0.84070.73630.51820.052*0.338 (4)
C2C0.7572 (7)0.8018 (5)0.6752 (4)0.0309 (14)0.338 (4)
C3C0.6651 (6)0.7736 (5)0.7898 (6)0.0416 (17)0.338 (4)
H3CA0.59850.71060.80530.050*0.338 (4)
C4C0.6704 (8)0.8374 (8)0.8819 (5)0.053 (2)0.338 (4)
H4CA0.60740.81810.96030.064*0.338 (4)
C5C0.7678 (11)0.9295 (8)0.8593 (7)0.075 (5)0.338 (4)
H5CA0.77140.97310.92230.090*0.338 (4)
C6C0.8599 (9)0.9577 (7)0.7447 (8)0.057 (3)0.338 (4)
H6CA0.92651.02070.72930.068*0.338 (4)
C7C0.8547 (6)0.8939 (6)0.6526 (5)0.0482 (19)0.338 (4)
C8C0.9529 (9)0.9303 (7)0.5317 (9)0.067 (2)0.338 (4)
H8CA1.01220.99470.53420.101*0.338 (4)
H8CB1.00810.86200.51040.101*0.338 (4)
H8CC0.90020.95810.47080.101*0.338 (4)
C9C0.6485 (10)0.7893 (8)0.4994 (8)0.045 (3)0.338 (4)
C10C0.7073 (8)0.8359 (8)0.3758 (8)0.057 (3)0.338 (4)
H10B0.80340.82600.34340.069*0.338 (4)
C11C0.6255 (12)0.8969 (7)0.2996 (7)0.081 (5)0.338 (4)
H11B0.66560.92870.21520.097*0.338 (4)
C12C0.4848 (11)0.9113 (8)0.3471 (10)0.064 (4)0.338 (4)
H12B0.42890.95300.29500.077*0.338 (4)
C13C0.4260 (8)0.8648 (8)0.4707 (10)0.074 (3)0.338 (4)
H13B0.32990.87460.50310.089*0.338 (4)
C14C0.5079 (11)0.8038 (7)0.5468 (7)0.069 (3)0.338 (4)
H14B0.46770.77200.63130.083*0.338 (4)
O1B0.78560 (18)0.46162 (16)0.89387 (15)0.0545 (4)
O2B0.6057 (2)0.4845 (2)1.10418 (19)0.0708 (6)
O3B0.71427 (19)0.50961 (19)1.23996 (16)0.0624 (5)
O4B1.0321 (2)0.85253 (18)1.1050 (2)0.0723 (6)
O5B1.1774 (2)0.8672 (2)0.9274 (2)0.0818 (7)
O6B1.0764 (2)0.6666 (2)0.62610 (18)0.0766 (6)
O7B0.98789 (19)0.4863 (2)0.68726 (18)0.0680 (6)
N1B0.70630 (19)0.52022 (17)1.13249 (17)0.0461 (5)
N2B1.0733 (3)0.8227 (2)1.0032 (2)0.0606 (6)
N3B1.0114 (2)0.5869 (2)0.70603 (19)0.0574 (6)
C1B0.8494 (2)0.5445 (2)0.9157 (2)0.0429 (5)
C2B0.8186 (2)0.58148 (19)1.03509 (19)0.0406 (5)
C3B0.8897 (2)0.6690 (2)1.0645 (2)0.0434 (5)
H3BA0.86580.68761.14490.052*
C4B0.9972 (2)0.7300 (2)0.9748 (2)0.0474 (5)
C5B1.0340 (2)0.7033 (2)0.8576 (2)0.0491 (6)
H5BA1.10690.74690.79670.059*
C6B0.9642 (2)0.6133 (2)0.8304 (2)0.0466 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.140 (2)0.0331 (9)0.1071 (17)0.0224 (10)−0.0862 (16)−0.0234 (10)
N1A0.0622 (12)0.0382 (9)0.0454 (10)0.0079 (8)−0.0212 (9)−0.0178 (8)
C1A0.057 (2)0.0313 (15)0.0513 (19)−0.0021 (14)−0.0189 (17)−0.0076 (14)
C2A0.062 (4)0.031 (3)0.071 (5)0.005 (2)−0.030 (3)−0.016 (3)
C3A0.058 (3)0.041 (3)0.079 (4)0.008 (2)−0.026 (3)−0.004 (3)
C4A0.080 (3)0.049 (3)0.070 (3)−0.006 (2)−0.008 (3)−0.008 (2)
C5A0.091 (4)0.035 (3)0.054 (3)−0.005 (2)−0.029 (3)−0.0009 (19)
C6A0.073 (4)0.032 (3)0.072 (4)0.004 (2)−0.044 (3)−0.020 (3)
C7A0.055 (3)0.036 (2)0.056 (3)−0.0089 (19)−0.018 (2)−0.019 (2)
C8A0.057 (2)0.046 (2)0.077 (3)0.0000 (16)−0.018 (2)−0.0214 (19)
C9A0.082 (4)0.0247 (16)0.065 (3)−0.0023 (19)−0.044 (3)−0.0008 (18)
C10A0.111 (5)0.043 (2)0.064 (3)−0.020 (3)−0.033 (3)−0.005 (2)
C11A0.160 (7)0.047 (3)0.064 (3)−0.026 (4)−0.050 (4)−0.003 (2)
C12A0.140 (6)0.035 (4)0.073 (5)0.000 (4)−0.073 (4)−0.003 (3)
C13A0.093 (4)0.031 (3)0.145 (7)0.011 (3)−0.079 (4)−0.021 (3)
C14A0.074 (4)0.041 (3)0.121 (5)0.001 (2)−0.054 (4)−0.025 (3)
C15A0.0719 (16)0.0363 (11)0.0548 (13)0.0091 (10)−0.0261 (12)−0.0140 (10)
C16A0.0583 (13)0.0382 (11)0.0546 (13)0.0084 (9)−0.0244 (11)−0.0189 (10)
C17A0.0827 (18)0.0481 (13)0.0508 (14)−0.0061 (12)−0.0209 (13)−0.0134 (11)
C18A0.0833 (18)0.0522 (14)0.0529 (14)0.0280 (13)−0.0283 (13)−0.0222 (11)
C1C0.048 (4)0.041 (3)0.041 (3)0.000 (3)−0.010 (3)−0.008 (3)
C2C0.030 (3)0.027 (4)0.036 (3)−0.005 (3)−0.011 (3)−0.001 (3)
C3C0.049 (4)0.040 (4)0.037 (4)0.006 (3)−0.019 (4)0.001 (3)
C4C0.067 (5)0.049 (5)0.048 (4)0.021 (4)−0.021 (4)−0.017 (4)
C5C0.076 (7)0.036 (8)0.133 (16)0.004 (5)−0.057 (9)−0.029 (9)
C6C0.097 (7)0.021 (4)0.067 (6)0.004 (4)−0.045 (5)−0.014 (3)
C7C0.058 (5)0.029 (4)0.063 (5)−0.001 (3)−0.027 (4)−0.007 (3)
C8C0.066 (5)0.050 (4)0.080 (6)−0.009 (4)−0.006 (4)−0.010 (4)
C9C0.070 (7)0.029 (5)0.047 (7)0.001 (4)−0.032 (6)−0.012 (4)
C10C0.072 (6)0.043 (6)0.066 (7)0.005 (4)−0.045 (6)0.001 (5)
C11C0.138 (14)0.036 (6)0.092 (9)−0.004 (7)−0.079 (10)−0.001 (5)
C12C0.102 (11)0.029 (5)0.083 (8)0.002 (5)−0.056 (8)−0.019 (5)
C13C0.096 (8)0.050 (5)0.100 (10)−0.004 (6)−0.047 (8)−0.038 (6)
C14C0.110 (10)0.048 (6)0.075 (7)0.018 (5)−0.054 (7)−0.039 (5)
O1B0.0585 (10)0.0651 (11)0.0472 (9)−0.0057 (8)−0.0170 (7)−0.0212 (8)
O2B0.0593 (11)0.0916 (15)0.0678 (12)−0.0224 (10)−0.0065 (9)−0.0355 (11)
O3B0.0582 (10)0.0834 (13)0.0450 (9)−0.0066 (9)−0.0144 (8)−0.0062 (9)
O4B0.0985 (15)0.0594 (11)0.0697 (13)−0.0230 (10)−0.0421 (11)−0.0059 (10)
O5B0.0861 (15)0.0765 (14)0.0795 (14)−0.0389 (12)−0.0260 (12)0.0090 (11)
O6B0.0816 (14)0.0921 (16)0.0471 (11)0.0039 (12)−0.0065 (10)−0.0027 (10)
O7B0.0557 (11)0.0980 (16)0.0585 (11)0.0003 (10)−0.0114 (8)−0.0363 (11)
N1B0.0460 (10)0.0497 (11)0.0460 (10)−0.0003 (8)−0.0126 (8)−0.0148 (8)
N2B0.0753 (15)0.0520 (12)0.0589 (13)−0.0151 (11)−0.0351 (12)0.0054 (10)
N3B0.0517 (11)0.0799 (16)0.0392 (11)0.0083 (10)−0.0123 (9)−0.0079 (11)
C1B0.0445 (11)0.0504 (12)0.0400 (11)0.0042 (9)−0.0205 (9)−0.0115 (9)
C2B0.0436 (11)0.0416 (11)0.0403 (11)0.0020 (8)−0.0177 (9)−0.0069 (9)
C3B0.0520 (12)0.0425 (11)0.0412 (11)0.0013 (9)−0.0236 (10)−0.0056 (9)
C4B0.0529 (13)0.0437 (11)0.0501 (13)−0.0050 (9)−0.0282 (10)0.0009 (10)
C5B0.0473 (12)0.0542 (13)0.0440 (12)−0.0009 (10)−0.0195 (10)0.0059 (10)
C6B0.0460 (12)0.0581 (13)0.0390 (11)0.0088 (10)−0.0190 (9)−0.0078 (10)
Geometric parameters (Å, °) top
O1A—C1C1.208 (7)C1C—C2C1.548 (8)
O1A—C1A1.346 (4)C1C—H1CA1.0000
O1A—C15A1.425 (3)C2C—C3C1.3900
N1A—C16A1.491 (3)C2C—C7C1.3900
N1A—C17A1.494 (3)C3C—C4C1.3900
N1A—C18A1.495 (3)C3C—H3CA0.9500
N1A—H1AB0.9300C4C—C5C1.3900
C1A—C9A1.522 (4)C4C—H4CA0.9500
C1A—C2A1.549 (5)C5C—C6C1.3900
C1A—H1AA1.0000C5C—H5CA0.9500
C2A—C3A1.3900C6C—C7C1.3900
C2A—C7A1.3900C6C—H6CA0.9500
C3A—C4A1.3900C7C—C8C1.478 (10)
C3A—H3AA0.9500C8C—C8Ci1.789 (15)
C4A—C5A1.3900C8C—H8CA0.9600
C4A—H4AA0.9500C8C—H8CB0.9600
C5A—C6A1.3900C8C—H8CC0.9601
C5A—H5AA0.9500C9C—C10C1.3900
C6A—C7A1.3900C9C—C14C1.3900
C6A—H6AA0.9500C10C—C11C1.3900
C7A—C8A1.503 (6)C10C—H10B0.9500
C8A—H8AA0.9600C11C—C12C1.3900
C8A—H8AB0.9600C11C—H11B0.9500
C8A—H8AC0.9601C12C—C13C1.3900
C9A—C10A1.3900C12C—H12B0.9500
C9A—C14A1.3900C13C—C14C1.3900
C10A—C11A1.3900C13C—H8AA1.5316
C10A—H10A0.9500C13C—H13B0.9500
C11A—C12A1.3900C14C—H14B0.9500
C11A—H11A0.9500O1B—C1B1.242 (3)
C12A—C13A1.3900O2B—N1B1.225 (3)
C12A—H12A0.9500O3B—N1B1.223 (3)
C13A—C14A1.3900O4B—N2B1.238 (3)
C13A—H13A0.9500O5B—N2B1.231 (3)
C14A—H14A0.9500O6B—N3B1.221 (3)
C15A—C16A1.501 (3)O7B—N3B1.230 (3)
C15A—H15A0.9900N1B—C2B1.457 (3)
C15A—H15B0.9900N2B—C4B1.438 (3)
C16A—H16A0.9900N3B—C6B1.463 (3)
C16A—H16B0.9900C1B—C6B1.447 (3)
C17A—H17A0.9800C1B—C2B1.455 (3)
C17A—H17B0.9800C2B—C3B1.369 (3)
C17A—H17C0.9800C3B—C4B1.385 (3)
C18A—H18A0.9800C3B—H3BA0.9500
C18A—H18B0.9800C4B—C5B1.383 (3)
C18A—H18C0.9800C5B—C6B1.371 (3)
C1C—C9C1.528 (8)C5B—H5BA0.9500
C1C—O1A—C1A50.3 (4)O1A—C1C—C9C117.4 (6)
C1C—O1A—C15A128.2 (4)O1A—C1C—C2C114.9 (5)
C1A—O1A—C15A117.7 (2)C9C—C1C—C2C109.5 (6)
C16A—N1A—C17A110.9 (2)O1A—C1C—H1CA104.5
C16A—N1A—C18A112.23 (17)C9C—C1C—H1CA104.5
C17A—N1A—C18A110.01 (19)C2C—C1C—H1CA104.5
C16A—N1A—H1AB107.9C3C—C2C—C7C120.0
C17A—N1A—H1AB107.9C3C—C2C—C1C117.8 (5)
C18A—N1A—H1AB107.9C7C—C2C—C1C122.2 (5)
O1A—C1A—C9A108.7 (3)C2C—C3C—C4C120.0
O1A—C1A—C2A114.5 (3)C2C—C3C—H3CA120.0
C9A—C1A—C2A112.2 (3)C4C—C3C—H3CA120.0
O1A—C1A—H1AA107.0C3C—C4C—C5C120.0
C9A—C1A—H1AA107.0C3C—C4C—H4CA120.0
C2A—C1A—H1AA107.0C5C—C4C—H4CA120.0
C3A—C2A—C7A120.0C4C—C5C—C6C120.0
C3A—C2A—C1A118.9 (4)C4C—C5C—H5CA120.0
C7A—C2A—C1A121.0 (4)C6C—C5C—H5CA120.0
C4A—C3A—C2A120.0C5C—C6C—C7C120.0
C4A—C3A—H3AA120.0C5C—C6C—H6CA120.0
C2A—C3A—H3AA120.0C7C—C6C—H6CA120.0
C3A—C4A—C5A120.0C6C—C7C—C2C120.0
C3A—C4A—H4AA120.0C6C—C7C—C8C117.5 (6)
C5A—C4A—H4AA120.0C2C—C7C—C8C122.5 (6)
C4A—C5A—C6A120.0C7C—C8C—C8Ci129.1 (9)
C4A—C5A—H5AA120.0C7C—C8C—H8CA110.3
C6A—C5A—H5AA120.0C7C—C8C—H8CB110.1
C7A—C6A—C5A120.0C8Ci—C8C—H8CB111.1
C7A—C6A—H6AA120.0H8CA—C8C—H8CB109.5
C5A—C6A—H6AA120.0C7C—C8C—H8CC108.0
C6A—C7A—C2A120.0C8Ci—C8C—H8CC84.9
C6A—C7A—C8A117.6 (4)H8CA—C8C—H8CC109.5
C2A—C7A—C8A122.3 (4)H8CB—C8C—H8CC109.5
C7A—C8A—H8AA109.6C10C—C9C—C14C120.0
C7A—C8A—H8AB109.7C10C—C9C—C1C116.2 (7)
H8AA—C8A—H8AB109.5C14C—C9C—C1C123.8 (7)
C7A—C8A—H8AC109.2C11C—C10C—C9C120.0
H8AA—C8A—H8AC109.5C11C—C10C—H10B120.0
H8AB—C8A—H8AC109.5C9C—C10C—H10B120.0
C10A—C9A—C14A120.0C10C—C11C—C12C120.0
C10A—C9A—C1A120.0 (3)C10C—C11C—H11B120.0
C14A—C9A—C1A120.0 (3)C12C—C11C—H11B120.0
C9A—C10A—C11A120.0C11C—C12C—C13C120.0
C9A—C10A—H10A120.0C11C—C12C—H12B120.0
C11A—C10A—H10A120.0C13C—C12C—H12B120.0
C12A—C11A—C10A120.0C14C—C13C—C12C120.0
C12A—C11A—H11A120.0C14C—C13C—H8AA97.3
C10A—C11A—H11A120.0C12C—C13C—H8AA142.5
C11A—C12A—C13A120.0C14C—C13C—H13B120.0
C11A—C12A—H12A120.0C12C—C13C—H13B120.0
C13A—C12A—H12A120.0C13C—C14C—C9C120.0
C14A—C13A—C12A120.0C13C—C14C—H14B120.0
C14A—C13A—H13A120.0C9C—C14C—H14B120.0
C12A—C13A—H13A120.0O3B—N1B—O2B122.4 (2)
C13A—C14A—C9A120.0O3B—N1B—C2B118.62 (18)
C13A—C14A—H14A120.0O2B—N1B—C2B118.94 (19)
C9A—C14A—H14A120.0O5B—N2B—O4B122.7 (2)
O1A—C15A—C16A110.1 (2)O5B—N2B—C4B119.3 (2)
O1A—C15A—H15A109.6O4B—N2B—C4B118.0 (2)
C16A—C15A—H15A109.6O6B—N3B—O7B123.2 (2)
O1A—C15A—H15B109.6O6B—N3B—C6B117.2 (2)
C16A—C15A—H15B109.6O7B—N3B—C6B119.5 (2)
H15A—C15A—H15B108.2O1B—C1B—C6B125.6 (2)
N1A—C16A—C15A113.0 (2)O1B—C1B—C2B122.9 (2)
N1A—C16A—H16A109.0C6B—C1B—C2B111.48 (19)
C15A—C16A—H16A109.0C3B—C2B—C1B124.7 (2)
N1A—C16A—H16B109.0C3B—C2B—N1B116.68 (19)
C15A—C16A—H16B109.0C1B—C2B—N1B118.60 (18)
H16A—C16A—H16B107.8C2B—C3B—C4B118.8 (2)
N1A—C17A—H17A109.5C2B—C3B—H3BA120.6
N1A—C17A—H17B109.5C4B—C3B—H3BA120.6
H17A—C17A—H17B109.5C5B—C4B—C3B121.3 (2)
N1A—C17A—H17C109.5C5B—C4B—N2B118.8 (2)
H17A—C17A—H17C109.5C3B—C4B—N2B119.9 (2)
H17B—C17A—H17C109.5C6B—C5B—C4B119.3 (2)
N1A—C18A—H18A109.5C6B—C5B—H5BA120.4
N1A—C18A—H18B109.5C4B—C5B—H5BA120.4
H18A—C18A—H18B109.5C5B—C6B—C1B124.4 (2)
N1A—C18A—H18C109.5C5B—C6B—N3B116.5 (2)
H18A—C18A—H18C109.5C1B—C6B—N3B119.1 (2)
H18B—C18A—H18C109.5
C1C—O1A—C1A—C9A−68.1 (5)C5C—C6C—C7C—C2C0.0
C15A—O1A—C1A—C9A173.7 (3)C5C—C6C—C7C—C8C178.4 (6)
C1C—O1A—C1A—C2A58.2 (5)C3C—C2C—C7C—C6C0.0
C15A—O1A—C1A—C2A−60.0 (4)C1C—C2C—C7C—C6C−179.4 (6)
O1A—C1A—C2A—C3A−33.7 (4)C3C—C2C—C7C—C8C−178.4 (6)
C9A—C1A—C2A—C3A90.8 (4)C1C—C2C—C7C—C8C2.2 (8)
O1A—C1A—C2A—C7A150.0 (3)C6C—C7C—C8C—C8Ci−19.3 (14)
C9A—C1A—C2A—C7A−85.5 (4)C2C—C7C—C8C—C8Ci159.1 (10)
C7A—C2A—C3A—C4A0.0O1A—C1C—C9C—C10C−113.0 (6)
C1A—C2A—C3A—C4A−176.3 (4)C2C—C1C—C9C—C10C113.7 (6)
C2A—C3A—C4A—C5A0.0O1A—C1C—C9C—C14C68.7 (9)
C3A—C4A—C5A—C6A0.0C2C—C1C—C9C—C14C−64.6 (8)
C4A—C5A—C6A—C7A0.0C14C—C9C—C10C—C11C0.0
C5A—C6A—C7A—C2A0.0C1C—C9C—C10C—C11C−178.3 (8)
C5A—C6A—C7A—C8A−178.8 (3)C9C—C10C—C11C—C12C0.0
C3A—C2A—C7A—C6A0.0C10C—C11C—C12C—C13C0.0
C1A—C2A—C7A—C6A176.2 (4)C11C—C12C—C13C—C14C0.0
C3A—C2A—C7A—C8A178.7 (3)C12C—C13C—C14C—C9C0.0
C1A—C2A—C7A—C8A−5.0 (4)C10C—C9C—C14C—C13C0.0
O1A—C1A—C9A—C10A−113.1 (3)C1C—C9C—C14C—C13C178.2 (9)
C2A—C1A—C9A—C10A119.2 (4)O1B—C1B—C2B—C3B177.3 (2)
O1A—C1A—C9A—C14A66.9 (4)C6B—C1B—C2B—C3B−0.8 (3)
C2A—C1A—C9A—C14A−60.8 (4)O1B—C1B—C2B—N1B−1.3 (3)
C14A—C9A—C10A—C11A0.0C6B—C1B—C2B—N1B−179.36 (19)
C1A—C9A—C10A—C11A180.0 (3)O3B—N1B—C2B—C3B−29.4 (3)
C9A—C10A—C11A—C12A0.0O2B—N1B—C2B—C3B148.4 (2)
C10A—C11A—C12A—C13A0.0O3B—N1B—C2B—C1B149.3 (2)
C11A—C12A—C13A—C14A0.0O2B—N1B—C2B—C1B−32.9 (3)
C12A—C13A—C14A—C9A0.0C1B—C2B—C3B—C4B1.5 (3)
C10A—C9A—C14A—C13A0.0N1B—C2B—C3B—C4B−179.84 (19)
C1A—C9A—C14A—C13A−180.0 (3)C2B—C3B—C4B—C5B−0.6 (3)
C1C—O1A—C15A—C16A−152.5 (5)C2B—C3B—C4B—N2B179.8 (2)
C1A—O1A—C15A—C16A−92.8 (3)O5B—N2B—C4B—C5B−7.2 (4)
C17A—N1A—C16A—C15A161.73 (19)O4B—N2B—C4B—C5B174.2 (2)
C18A—N1A—C16A—C15A−74.8 (2)O5B—N2B—C4B—C3B172.5 (2)
O1A—C15A—C16A—N1A−65.3 (3)O4B—N2B—C4B—C3B−6.2 (3)
C1A—O1A—C1C—C9C−53.1 (6)C3B—C4B—C5B—C6B−1.1 (3)
C15A—O1A—C1C—C9C43.5 (9)N2B—C4B—C5B—C6B178.5 (2)
C1A—O1A—C1C—C2C77.7 (6)C4B—C5B—C6B—C1B1.9 (4)
C15A—O1A—C1C—C2C174.4 (4)C4B—C5B—C6B—N3B−178.1 (2)
O1A—C1C—C2C—C3C−43.8 (7)O1B—C1B—C6B—C5B−179.0 (2)
C9C—C1C—C2C—C3C90.7 (6)C2B—C1B—C6B—C5B−1.0 (3)
O1A—C1C—C2C—C7C135.6 (5)O1B—C1B—C6B—N3B0.9 (3)
C9C—C1C—C2C—C7C−89.8 (7)C2B—C1B—C6B—N3B178.98 (19)
C7C—C2C—C3C—C4C0.0O6B—N3B—C6B—C5B−21.7 (3)
C1C—C2C—C3C—C4C179.5 (6)O7B—N3B—C6B—C5B156.2 (2)
C2C—C3C—C4C—C5C0.0O6B—N3B—C6B—C1B158.3 (2)
C3C—C4C—C5C—C6C0.0O7B—N3B—C6B—C1B−23.8 (3)
C4C—C5C—C6C—C7C0.0
Symmetry codes: (i) −x+2, −y+2, −z+1.
Hydrogen-bond geometry (Å, °) top
Cg2 and Cg3 are the centroids of the C9A–C7A and C2C–C7C rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1A—H1AB···O1B0.931.852.661 (2)144
N1A—H1AB···O7B0.932.363.031 (3)129
C4A—H4AA···O4Bii0.952.463.346 (4)155
C16A—H16A···O3Biii0.992.573.519 (3)160
C17A—H17A···O2Biii0.982.573.470 (4)153
C18A—H18A···O6Biv0.982.413.167 (3)133
C18A—H18C···O4Bv0.982.363.317 (3)166
C8C—H8CB···O6B0.962.483.239 (9)136
C6A—H6AA···Cg2vi0.932.883.643 (2)138
C6A—H6AA···Cg3vi0.933.003.836 (4)148
C12C—H12B···Cg2vi0.932.623.492 (4)153
C12C—H12B···Cg3vi0.932.833.704 (4)153
Symmetry codes: (ii) x, y, z−1; (iii) −x+1, −y+1, −z+2; (iv) −x+2, −y+1, −z+1; (v) −x+2, −y+1, −z+2; (vi) −x+1, −y+2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
Cg2 and Cg3 are the centroids of the C9A–C7A and C2C–C7C rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1A—H1AB···O1B0.931.852.661 (2)144
N1A—H1AB···O7B0.932.363.031 (3)129
C4A—H4AA···O4Bi0.952.463.346 (4)155
C16A—H16A···O3Bii0.992.573.519 (3)160
C17A—H17A···O2Bii0.982.573.470 (4)153
C18A—H18A···O6Biii0.982.413.167 (3)133
C18A—H18C···O4Biv0.982.363.317 (3)166
C8C—H8CB···O6B0.962.483.239 (9)136
C6A—H6AA···Cg2v0.932.883.643 (2)138
C6A—H6AA···Cg3v0.933.003.836 (4)148
C12C—H12B···Cg2v0.932.623.492 (4)153
C12C—H12B···Cg3v0.932.833.704 (4)153
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+2; (iii) −x+2, −y+1, −z+1; (iv) −x+2, −y+1, −z+2; (v) −x+1, −y+2, −z+1.
Table 2
Cg···Cg π-stacking interactions (Å) Cg2, Cg3 and Cg5 are the centroids of rings C9A–C14A, C2C–C7C and C1B–C6B. Symmetry code: (i) 1-x, 2-y, 1-z top
CgI···CgJ (Å)CgI···Perp (Å)CgJ···Perp (Å)
Cg2···Cg5i3.677 (2)-3.616 (2)-3.6243 (9)
Cg3···Cg5i3.515 (3)-3.374 (3)3.3844 (9)
Acknowledgements top

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

references
References top

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Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.

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