supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

sj2729 scheme

Acta Cryst. (2010). E66, o674-o675    [ doi:10.1107/S1600536810006203 ]

Desipramine hydrochloride: a non-merohedrally twinned structure

J. P. Jasinski, R. J. Butcher, Q. N. M. Hakim Al-Arique, H. S. Yathirajan and A. R. Ramesha

Abstract top

The title compound, C18H23N2+·Cl-, is a non-merohedrally twinned salt [domains 0.9288 (3) and 0.0712 (3)] which crystallizes with four independent cation-anion pairs in the asymmetric unit. The seven-membered ring in each of the cations adopts a boat conformation, thus creating a butterfly effect within the ring system. The average value of the dihedral angle between the two aromatic rings in the four cations is 57.1 (1)°. The crystal packing is stabilized only slightly by a collection of intermediate N-H...Cl hydrogen-bonding interactions, which produce a weak, but cooperative, infinite, one-dimensional, intermolecular hydrogen-bond network along the a axis. A MOPAC PM3 computational calculation gives support to these observations.

Comment top

The pharmacological properties of the active metabolites of the antidepressants desipramine and citalopram have been described (Deupree et al., 2007). Desipramine, 10,11-dihydro-5-[3-(methylamino)propyl]-5H-dibenz[b,f]azepine is a tricyclic antidepressant (TCA) that inhibits the re-uptake of norepinephrine. Desipramine is an active metabolite of imipramine. Along with other tricyclics, desipramine has found use in treating neuropathic pain. The mechanism of action seems to involve the activation, through norepinephrine re-uptake inhibition, of descending pathways in the spinal cord that block pain signals from ascending to the brain. Desipramine is one of the most potent and selective medications in this respect. Desipramine hydrochloride works by increasing the amount of serotonin and norepinephrine in the brain so that the feeling of depression is prevented or relieved. By a separate mechanism, desipramine hydrochloride may also reduce pain related to peripheral neuropathy. The effect of desipramine hydrochloride on peripheral sympathetic nerve activity is reported (Cohen et al., 1990). A sensitive spectrophotometric method has been developed for the determination of desipramine hydrochloride (Nagaraja et al., 2000). Desipramine hydrochloride is proposed as a new reagent for detection of microamounts of blood in urine (Ahmed et al., 2002).

The crystal structures of imipramine hydrochloride (Post et al. 1975), nortriptyline hydrochloride (Klein et al. 1991), amitriptyline hydrochloride (Klein et al. 1994), 5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[a,d][7]annulen-5-o l derived from the hydrolysis of amitriptyline (Portalone et al., 2007) and amitriptylinium picrate (Bindya et al., 2007) have been reported. The crystal structures of desipraminium picrate and desipraminium picrate hydrate have also been recently reported (Swamy et al., 2007; Harrison et al., 2007). In continuation of our work on related pharmaceutical compounds (Butcher et al., 2007) and in view of the importance of desipramine, this paper reports the crystal structure of the title compound, C18H23N2+ . Cl-, (I).

The title compound, (I), is a non-merohedrally twinned salt and crystallizes with four independent cation-anion pairs (A,B,C,D) in the asymmetric unit cell. Cation-anion pair A is shown in Fig. 1. These cation-anion pairs form two sets of a pair of enantiomers connected by a salt linkage between the proton that has been transfered from the hydrogen chloride to the desipramine (dp) group resulting in the protonation of the secondary-amine N atom of the side chain yielding an -NH2+- grouping and a chloride anion (Fig. 2). The dihedral angle between the C1—C6 and C9—C14 ring planes in the cation is 57.5 (5)° (A), 57.8 (3)° (B), 55.8 (3)° (C) and 57.1 (9)° (D), respectively. The average value, 57.1 (1)°, is significantly higher than that observed in the related structures of desipraminum picrate, 52.79 (6)°, (Swamy et al., 2007) and desipraminum picrate monohydrate, 53.92 (8)°, (Harrison et al., 2007). The bond-angle sum for N1 is 353.44 (15)° (A), 353.08 (15)° (B), 353.98 (15)° (C) and 353.61 (15)° (D), respectively, which indicates a slightly distorted sp2 hybridization and a poorly aligned p orbital with the π cloud of adjacent benzene rings. The least squares plane of the C1/C14/C15/N1 group makes dihedral angles of 40.6 (8)° (A), 38.5 (4)° (B), 38.6 (1)° (C), 39.3 (8)° with the C1—C6 ring planes (average = 39.3 (1)°) and 57.7 (5)° (A), 56.1 (3)° (B), 57.1 (6)° (C), 56.8 (4)° (D) with the C9—C14 ring planes (average = 56.9 (7)°), respectively. In each of the four cations in the asymmetric unit the seven-membered ring approximates a boat thereby creating a butterfly effect within the ring system.

Crystal packing is stabilized only slightly by a collection of intermediate N—H···Cl hydrogen bonding interactions (Table 1) which produces a weak, but cooperative, infinite, one-dimensional, intermolecular hydrogen bond network along the a axis of the unit cell (Fig. 3).

From the results of a MOPAC PM3 computational calculation (Schmidt & Polik, 2007), the dihedral angle between the C1—C6 and C9—C14 ring planes in the cation is found to be 57.7 (3)°, just slightly higher than the 57.1 (1)° average value of the four molecules in the asymmetric unit. The least squares plane of the C1/C14/C15/N1 group makes dihedral angles of 40.09° with the C1—C6 ring plane and 55.60° with the C9—C14 ring plane, which is slightly higher than the C1—C6 ring plane average value in the crystal (39.3 (1)°) and slightly lower than the C9—C14 ring plane average value (56.9 (7)°) in the crystal. From these observations it is clear that the collective effect of the intermediate hydrogen bond interactions in (I) only slightly influences crystal packing stability, in sharp contrast to the traditional hydrogen bonding effects observed in desipraminium picrate (Swamy et al., 2007) and desipraminium picrate monohydrate (Harrison et al., 2007), respectively, which resulted in much greater deviations in these values.

Related literature top

For related structures, see: Bindya et al. (2007); Butcher et al. (2007); Harrison et al. (2007); Klein et al. (1991, 1994); Portalone et al. (2007); Post et al. (1975); Swamy et al. (2007). For pharmaceutical uses of desipramine, see: Deupree et al. (2007); Cohen et al. (1990). For the analysis of desipramine hydrochloride, see: Nagaraja et al. (2000) and for its use in the detection of trace amounts of blood in urine, see: Ahmed et al. (2002). For MOPAC PM3 calculations, see: Schmidt & Polik (2007).

Experimental top

The title compound was obtained as a gift sample from R.L. Fine Chem, Bangalore, India. The compound was used without further purification. X-ray quality crystals (m.p. 458-461 K) were obtained by slow evaporation from an aqueous solution.

Refinement top

The crystal is a non-merohedral twin with domains of 0.9288 (3) and 0.0712 (3). The structure was solved using the non-overlapping reflections and refined using all data in a SHELXTL HKLF5 format. In this format reflections cannot be merged hence the data appears to be more than 100% complete.

All of the H atoms were placed in their calculated positions and then refined using the riding model with N—H = 0.92, C—H = 0.95-0.99 Å, and with Uiso(H) = 1.18-1.51Ueq(C,N).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (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 cation-anion pair A for C18H23N2+.Cl-, (I), showing atom labeling scheme and 50% probability displacement ellipsoids. H atoms are presented as small circles of arbitrary radius.
[Figure 2] Fig. 2. Molecular structure of C18H23N2+.Cl- showing one of two sets of a pair of enantiomers connected by a salt linkage between the proton that has been transfered from the hydrogen chloride to the desipramine (dp) group resulting in the protonation of the secondary-amine N atom of the side chain yielding an -NH2+- grouping and a chloride anion.
[Figure 3] Fig. 3. Packing diagram of the title compound, (I), viewed down the c axis. Dashed lines indicate weak intermediate intermolecular N—H···Cl interactions which produce an infinite network arranged along the c axis of the unit cell.
Desipramine hydrochloride top
Crystal data top
C18H23N2+·Cl−Z = 8
Mr = 302.83F(000) = 1296
Triclinic, P1Dx = 1.210 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.7258 (3) ÅCell parameters from 19411 reflections
b = 15.9997 (6) Åθ = 4.8–32.7°
c = 20.6088 (8) ŵ = 0.23 mm−1
α = 107.347 (3)°T = 110 K
β = 89.960 (2)°Chunk, colorless
γ = 99.414 (2)°0.53 × 0.44 × 0.32 mm
V = 3326.0 (2) Å3
Data collection top
Oxford Diffraction Xcalibur
diffractometer with Ruby (Gemini Mo) detector		60082 independent reflections
Radiation source: Enhance (Mo) X-ray Source33887 reflections with I > 2σ(I)
graphiteRint = 0.0000
Detector resolution: 10.5081 pixels mm-1θmax = 32.9°, θmin = 4.8°
ω scansh = −15→16
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		k = −23→24
Tmin = 0.806, Tmax = 1.000l = −31→30
60082 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)] = 0.083Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.280H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.1596P)2 + 0.0167P]
where P = (Fo2 + 2Fc2)/3
60082 reflections(Δ/σ)max = 0.001
762 parametersΔρmax = 1.40 e Å−3
0 restraintsΔρmin = −0.93 e Å−3
Crystal data top
C18H23N2+·Cl−γ = 99.414 (2)°
Mr = 302.83V = 3326.0 (2) Å3
Triclinic, P1Z = 8
a = 10.7258 (3) ÅMo Kα radiation
b = 15.9997 (6) ŵ = 0.23 mm−1
c = 20.6088 (8) ÅT = 110 K
α = 107.347 (3)°0.53 × 0.44 × 0.32 mm
β = 89.960 (2)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with Ruby (Gemini Mo) detector		60082 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		33887 reflections with I > 2σ(I)
Tmin = 0.806, Tmax = 1.000Rint = 0.0000
60082 measured reflectionsθmax = 32.9°
Refinement top
R[F2 > 2σ(F2)] = 0.083H-atom parameters constrained
wR(F2) = 0.280Δρmax = 1.40 e Å−3
S = 1.09Δρmin = −0.93 e Å−3
60082 reflectionsAbsolute structure: ?
762 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
Cl10.21608 (4)0.50056 (3)0.74908 (3)0.02317 (11)
Cl20.28400 (4)0.47582 (4)0.99515 (3)0.02684 (12)
Cl30.70231 (4)0.47109 (4)0.49442 (3)0.02741 (12)
Cl4−0.20743 (4)0.50182 (4)0.75046 (3)0.02630 (11)
N1A0.62641 (14)0.73248 (10)0.67767 (8)0.0178 (3)
N2A0.47318 (14)0.44709 (10)0.58136 (8)0.0209 (3)
H2AB0.41350.47330.56630.025*
H2AC0.54720.45900.56070.025*
N1B0.12250 (14)0.74135 (10)0.68520 (8)0.0184 (3)
N2B−0.00850 (14)0.45333 (10)0.64241 (8)0.0200 (3)
H2BB0.06380.47290.67040.024*
H2BC−0.07540.47010.66820.024*
N1C0.00555 (14)0.26122 (10)0.81590 (8)0.0198 (3)
N2C0.01723 (14)0.54983 (10)0.85746 (8)0.0203 (3)
H2CB0.07960.52940.82940.024*
H2CC−0.05780.53380.83170.024*
N1D0.51015 (14)0.26770 (10)0.82101 (8)0.0181 (3)
N2D0.50186 (14)0.55342 (10)0.91841 (8)0.0199 (3)
H2DB0.42900.52890.93420.024*
H2DC0.56930.53930.93800.024*
C1A0.64897 (16)0.77542 (12)0.74864 (10)0.0166 (4)
C2A0.71358 (18)0.73653 (14)0.78838 (11)0.0246 (4)
H2AA0.73830.68070.76730.030*
C3A0.74191 (19)0.77664 (16)0.85651 (11)0.0304 (5)
H3AA0.78760.74930.88150.036*
C4A0.70423 (19)0.85697 (15)0.88913 (11)0.0299 (5)
H4AA0.72300.88520.93640.036*
C5A0.63804 (19)0.89520 (14)0.85063 (11)0.0257 (4)
H5AA0.61170.95010.87280.031*
C6A0.60863 (16)0.85672 (13)0.78113 (10)0.0196 (4)
C7A0.53339 (18)0.90674 (13)0.74724 (11)0.0237 (4)
H7AA0.45740.91800.77360.028*
H7AB0.58570.96530.75150.028*
C8A0.48966 (17)0.86384 (14)0.67260 (11)0.0236 (4)
H8AA0.43330.80640.66740.028*
H8AB0.44050.90290.65790.028*
C9A0.59992 (17)0.84817 (13)0.62775 (10)0.0199 (4)
C10A0.6371 (2)0.89616 (14)0.58272 (11)0.0277 (5)
H10A0.59230.94160.57980.033*
C11A0.7390 (2)0.87870 (14)0.54186 (11)0.0294 (5)
H11A0.76220.91100.51060.035*
C12A0.80635 (19)0.81377 (14)0.54719 (11)0.0262 (4)
H12A0.87700.80240.52010.031*
C13A0.77070 (17)0.76544 (13)0.59198 (10)0.0213 (4)
H13A0.81640.72060.59510.026*
C14A0.66759 (16)0.78258 (12)0.63254 (9)0.0163 (4)
C15A0.62178 (16)0.63576 (12)0.65202 (10)0.0183 (4)
H15A0.69990.62040.66750.022*
H15B0.61690.61630.60160.022*
C16A0.50702 (17)0.58786 (13)0.67781 (11)0.0219 (4)
H16A0.42970.60290.66100.026*
H16B0.51080.61060.72810.026*
C17A0.49516 (17)0.48699 (13)0.65663 (10)0.0199 (4)
H17A0.57360.47110.67140.024*
H17B0.42390.46210.67960.024*
C18A0.4296 (2)0.34976 (15)0.56104 (13)0.0407 (6)
H18A0.48960.32200.57990.061*
H18B0.42450.32590.51130.061*
H18C0.34590.33700.57850.061*
C1B0.16087 (16)0.78628 (12)0.75472 (10)0.0167 (4)
C2B0.26179 (18)0.76692 (13)0.78704 (11)0.0233 (4)
H2BA0.30860.72340.76200.028*
C3B0.29468 (19)0.81052 (14)0.85544 (11)0.0267 (4)
H3BA0.36440.79750.87680.032*
C4B0.2259 (2)0.87278 (14)0.89219 (11)0.0293 (5)
H4BA0.24640.90150.93930.035*
C5B0.1262 (2)0.89333 (14)0.86011 (11)0.0273 (4)
H5BA0.08060.93740.88550.033*
C6B0.09191 (17)0.85071 (13)0.79162 (10)0.0198 (4)
C7B−0.01698 (17)0.86960 (14)0.75529 (11)0.0234 (4)
H7BA−0.06770.90580.78910.028*
H7BB−0.07230.81280.73100.028*
C8B0.02855 (18)0.91882 (13)0.70444 (11)0.0231 (4)
H8BA−0.04670.93120.68350.028*
H8BB0.07930.97690.73010.028*
C9B0.10706 (16)0.87295 (13)0.64727 (10)0.0188 (4)
C10B0.14031 (18)0.91826 (14)0.59927 (11)0.0256 (4)
H10B0.11660.97480.60620.031*
C11B0.2061 (2)0.88405 (15)0.54239 (11)0.0299 (5)
H11B0.22750.91660.51100.036*
C12B0.23969 (19)0.80178 (15)0.53218 (11)0.0300 (5)
H12B0.28410.77700.49320.036*
C13B0.20918 (17)0.75494 (13)0.57840 (10)0.0225 (4)
H13B0.23150.69770.57000.027*
C14B0.14582 (16)0.79036 (12)0.63743 (10)0.0177 (4)
C15B0.12217 (17)0.64509 (12)0.66252 (10)0.0200 (4)
H15C0.12050.62290.70260.024*
H15D0.20060.63290.63880.024*
C16B0.00773 (17)0.59651 (13)0.61475 (11)0.0220 (4)
H16C−0.07010.60800.63930.026*
H16D0.00820.62110.57600.026*
C17B0.00322 (17)0.49670 (13)0.58728 (10)0.0200 (4)
H17C−0.06970.47040.55400.024*
H17D0.08120.48480.56310.024*
C18B−0.0284 (2)0.35501 (14)0.61524 (13)0.0350 (5)
H18D−0.10340.33400.58390.052*
H18E−0.04070.32940.65290.052*
H18F0.04590.33660.59090.052*
C1C0.00597 (16)0.21325 (12)0.86386 (9)0.0166 (4)
C2C0.08932 (18)0.24836 (14)0.92181 (10)0.0245 (4)
H2CA0.14210.30440.92870.029*
C3C0.0962 (2)0.20309 (16)0.96890 (11)0.0319 (5)
H3CA0.15410.22791.00730.038*
C4C0.0192 (2)0.12169 (15)0.96061 (11)0.0303 (5)
H4CA0.02500.08940.99210.036*
C5C−0.06634 (19)0.08886 (14)0.90512 (11)0.0251 (4)
H5CA−0.12130.03410.90010.030*
C6C−0.07610 (17)0.13206 (13)0.85609 (10)0.0192 (4)
C7C−0.17924 (17)0.08723 (13)0.79940 (11)0.0222 (4)
H7CA−0.15790.02910.77310.027*
H7CB−0.25980.07500.82110.027*
C8C−0.20272 (17)0.13679 (14)0.74909 (10)0.0228 (4)
H8CA−0.27340.10140.71650.027*
H8CB−0.22780.19420.77410.027*
C9C−0.08723 (17)0.15374 (12)0.71060 (10)0.0182 (4)
C10C−0.0802 (2)0.11172 (14)0.64149 (10)0.0261 (4)
H10C−0.15030.06980.61710.031*
C11C0.0282 (2)0.13006 (14)0.60735 (11)0.0273 (4)
H11C0.03120.10150.56000.033*
C12C0.13166 (19)0.19016 (14)0.64277 (11)0.0260 (4)
H12C0.20620.20210.61980.031*
C13C0.12624 (17)0.23284 (13)0.71167 (11)0.0236 (4)
H13C0.19720.27400.73590.028*
C14C0.01636 (16)0.21541 (12)0.74571 (9)0.0167 (4)
C15C0.05277 (17)0.35747 (12)0.83755 (10)0.0199 (4)
H15E0.06220.37880.79710.024*
H15F0.13700.37000.86140.024*
C16C−0.03885 (17)0.40641 (13)0.88492 (11)0.0227 (4)
H16E−0.12170.39530.85990.027*
H16F−0.05170.38180.92360.027*
C17C0.00607 (17)0.50606 (13)0.91257 (10)0.0213 (4)
H17E−0.05420.53260.94560.026*
H17F0.08950.51760.93700.026*
C18C0.0473 (2)0.64785 (14)0.88395 (13)0.0357 (5)
H18G−0.01510.66980.91660.054*
H18H0.04500.67310.84620.054*
H18I0.13200.66570.90660.054*
C1D0.51377 (16)0.22531 (12)0.74997 (9)0.0160 (3)
C2D0.59751 (17)0.26645 (14)0.71156 (10)0.0237 (4)
H2DA0.64760.32270.73340.028*
C3D0.60846 (19)0.22704 (16)0.64306 (11)0.0305 (5)
H3DA0.66590.25600.61830.037*
C4D0.5352 (2)0.14472 (16)0.61007 (11)0.0309 (5)
H4DA0.54380.11620.56310.037*
C5D0.44992 (18)0.10531 (14)0.64707 (10)0.0239 (4)
H5DA0.39840.04990.62430.029*
C6D0.43638 (16)0.14369 (12)0.71671 (10)0.0183 (4)
C7D0.33540 (18)0.09215 (13)0.74909 (11)0.0235 (4)
H7DA0.35980.03370.74480.028*
H7DB0.25490.08060.72190.028*
C8D0.30945 (18)0.13415 (14)0.82366 (11)0.0247 (4)
H8DA0.27970.19100.82870.030*
H8DB0.24130.09420.83750.030*
C9D0.42521 (18)0.15095 (13)0.86956 (10)0.0221 (4)
C10D0.4375 (2)0.10296 (14)0.91468 (12)0.0300 (5)
H10D0.37080.05680.91650.036*
C11D0.5457 (2)0.12130 (14)0.95734 (12)0.0316 (5)
H11D0.55170.08890.98880.038*
C12D0.6448 (2)0.18731 (14)0.95360 (11)0.0279 (5)
H12D0.71940.19950.98200.033*
C13D0.63488 (18)0.23548 (13)0.90830 (10)0.0220 (4)
H13D0.70260.28060.90570.026*
C14D0.52467 (17)0.21739 (12)0.86643 (10)0.0176 (4)
C15D0.55222 (16)0.36414 (12)0.84757 (10)0.0188 (4)
H15G0.63830.37990.83260.023*
H15H0.55590.38270.89800.023*
C16D0.46105 (17)0.41302 (13)0.82192 (11)0.0222 (4)
H16G0.45330.39040.77160.027*
H16H0.37640.39880.83900.027*
C17D0.50053 (17)0.51341 (13)0.84319 (10)0.0198 (4)
H17G0.58600.52830.82730.024*
H17H0.44110.53920.82120.024*
C18D0.5113 (2)0.65135 (15)0.93995 (13)0.0399 (6)
H18J0.58560.67770.92070.060*
H18K0.51960.67430.98970.060*
H18L0.43490.66680.92370.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01509 (19)0.0342 (3)0.0256 (3)0.00686 (18)0.00291 (16)0.0158 (2)
Cl20.01409 (19)0.0427 (3)0.0228 (3)0.00182 (19)0.00046 (16)0.0101 (2)
Cl30.0195 (2)0.0429 (3)0.0234 (3)0.0157 (2)0.00421 (17)0.0099 (2)
Cl40.0160 (2)0.0403 (3)0.0278 (3)0.00850 (19)0.00336 (17)0.0162 (2)
N1A0.0245 (8)0.0154 (7)0.0146 (8)0.0052 (6)0.0025 (6)0.0052 (7)
N2A0.0180 (7)0.0232 (8)0.0226 (9)0.0027 (6)−0.0022 (6)0.0091 (7)
N1B0.0269 (8)0.0156 (7)0.0137 (8)0.0065 (6)0.0001 (6)0.0046 (7)
N2B0.0168 (7)0.0228 (8)0.0211 (9)0.0034 (6)−0.0001 (6)0.0079 (7)
N1C0.0263 (8)0.0177 (8)0.0137 (8)−0.0017 (6)0.0024 (6)0.0051 (7)
N2C0.0177 (7)0.0248 (8)0.0205 (9)0.0064 (6)0.0029 (6)0.0084 (7)
N1D0.0249 (8)0.0165 (7)0.0136 (8)0.0029 (6)−0.0006 (6)0.0059 (7)
N2D0.0178 (7)0.0239 (8)0.0208 (9)0.0069 (6)0.0042 (6)0.0090 (7)
C1A0.0156 (8)0.0202 (9)0.0156 (9)0.0005 (7)0.0033 (6)0.0092 (8)
C2A0.0250 (9)0.0299 (11)0.0224 (11)0.0067 (8)0.0034 (8)0.0120 (9)
C3A0.0292 (10)0.0434 (13)0.0227 (12)0.0062 (9)−0.0005 (8)0.0162 (11)
C4A0.0329 (11)0.0382 (12)0.0148 (11)−0.0039 (9)−0.0001 (8)0.0076 (10)
C5A0.0297 (10)0.0243 (10)0.0176 (11)−0.0001 (8)0.0033 (8)0.0006 (9)
C6A0.0175 (8)0.0226 (9)0.0176 (10)0.0015 (7)0.0029 (7)0.0052 (8)
C7A0.0242 (9)0.0219 (10)0.0248 (11)0.0050 (8)0.0043 (8)0.0060 (9)
C8A0.0208 (9)0.0279 (10)0.0257 (11)0.0082 (8)−0.0005 (7)0.0115 (9)
C9A0.0204 (9)0.0213 (9)0.0184 (10)0.0027 (7)−0.0003 (7)0.0068 (8)
C10A0.0376 (11)0.0246 (10)0.0252 (12)0.0091 (9)0.0022 (9)0.0118 (10)
C11A0.0432 (12)0.0234 (10)0.0224 (12)0.0001 (9)0.0057 (9)0.0113 (9)
C12A0.0267 (10)0.0299 (11)0.0180 (11)−0.0003 (8)0.0063 (8)0.0040 (9)
C13A0.0221 (9)0.0246 (10)0.0182 (10)0.0071 (8)0.0015 (7)0.0062 (8)
C14A0.0167 (8)0.0182 (9)0.0132 (9)0.0000 (7)−0.0018 (6)0.0050 (8)
C15A0.0183 (8)0.0185 (9)0.0192 (10)0.0057 (7)0.0053 (7)0.0060 (8)
C16A0.0199 (9)0.0242 (10)0.0224 (10)0.0044 (7)0.0049 (7)0.0079 (9)
C17A0.0187 (8)0.0252 (10)0.0188 (10)0.0034 (7)0.0036 (7)0.0113 (8)
C18A0.0579 (15)0.0249 (11)0.0332 (14)−0.0072 (10)−0.0118 (11)0.0073 (11)
C1B0.0173 (8)0.0186 (9)0.0171 (10)0.0047 (7)0.0028 (6)0.0090 (8)
C2B0.0231 (9)0.0269 (10)0.0231 (11)0.0075 (8)0.0027 (7)0.0107 (9)
C3B0.0268 (10)0.0303 (11)0.0258 (12)0.0020 (8)−0.0062 (8)0.0143 (10)
C4B0.0425 (12)0.0276 (11)0.0162 (11)0.0013 (9)−0.0049 (9)0.0069 (9)
C5B0.0391 (12)0.0242 (10)0.0192 (11)0.0114 (9)0.0033 (8)0.0042 (9)
C6B0.0221 (9)0.0221 (9)0.0175 (10)0.0055 (7)0.0021 (7)0.0085 (8)
C7B0.0210 (9)0.0268 (10)0.0253 (11)0.0097 (8)0.0058 (7)0.0090 (9)
C8B0.0245 (9)0.0227 (10)0.0260 (11)0.0081 (8)0.0018 (8)0.0111 (9)
C9B0.0151 (8)0.0238 (9)0.0197 (10)0.0019 (7)−0.0003 (7)0.0106 (8)
C10B0.0262 (10)0.0271 (10)0.0261 (12)0.0016 (8)−0.0015 (8)0.0134 (9)
C11B0.0343 (11)0.0377 (12)0.0190 (11)−0.0039 (9)0.0005 (8)0.0159 (10)
C12B0.0284 (10)0.0389 (12)0.0173 (11)−0.0007 (9)0.0047 (8)0.0039 (10)
C13B0.0236 (9)0.0234 (10)0.0190 (10)0.0037 (8)0.0019 (7)0.0044 (9)
C14B0.0171 (8)0.0211 (9)0.0152 (9)0.0002 (7)−0.0019 (6)0.0075 (8)
C15B0.0225 (9)0.0168 (9)0.0207 (10)0.0057 (7)−0.0012 (7)0.0043 (8)
C16B0.0196 (8)0.0222 (9)0.0246 (11)0.0050 (7)−0.0016 (7)0.0067 (9)
C17B0.0196 (8)0.0245 (10)0.0165 (10)0.0040 (7)−0.0011 (7)0.0070 (8)
C18B0.0446 (13)0.0212 (10)0.0376 (14)0.0008 (9)−0.0074 (10)0.0091 (10)
C1C0.0183 (8)0.0215 (9)0.0122 (9)0.0083 (7)0.0047 (6)0.0057 (8)
C2C0.0259 (10)0.0262 (10)0.0180 (10)0.0046 (8)−0.0012 (7)0.0018 (9)
C3C0.0382 (12)0.0413 (13)0.0169 (11)0.0169 (10)−0.0027 (8)0.0047 (10)
C4C0.0444 (13)0.0361 (12)0.0190 (11)0.0194 (10)0.0058 (9)0.0148 (10)
C5C0.0280 (10)0.0276 (10)0.0254 (12)0.0098 (8)0.0069 (8)0.0140 (9)
C6C0.0180 (8)0.0235 (9)0.0200 (10)0.0086 (7)0.0046 (7)0.0098 (8)
C7C0.0205 (9)0.0223 (9)0.0249 (11)0.0030 (7)0.0026 (7)0.0092 (9)
C8C0.0180 (8)0.0292 (10)0.0215 (11)0.0030 (8)−0.0008 (7)0.0086 (9)
C9C0.0200 (8)0.0192 (9)0.0173 (10)0.0053 (7)0.0010 (7)0.0074 (8)
C10C0.0348 (11)0.0251 (10)0.0158 (10)0.0015 (8)−0.0018 (8)0.0043 (9)
C11C0.0428 (12)0.0258 (10)0.0154 (10)0.0113 (9)0.0052 (8)0.0063 (9)
C12C0.0308 (10)0.0292 (11)0.0242 (11)0.0114 (9)0.0115 (8)0.0142 (10)
C13C0.0203 (9)0.0277 (10)0.0248 (11)0.0033 (8)0.0024 (7)0.0111 (9)
C14C0.0189 (8)0.0188 (9)0.0146 (9)0.0053 (7)0.0007 (6)0.0069 (8)
C15C0.0220 (9)0.0178 (9)0.0181 (10)−0.0015 (7)0.0032 (7)0.0054 (8)
C16C0.0194 (9)0.0244 (10)0.0258 (11)0.0026 (7)0.0045 (7)0.0103 (9)
C17C0.0200 (9)0.0282 (10)0.0180 (10)0.0067 (8)0.0030 (7)0.0091 (9)
C18C0.0495 (14)0.0235 (11)0.0339 (14)0.0067 (10)0.0088 (10)0.0080 (11)
C1D0.0152 (8)0.0217 (9)0.0135 (9)0.0067 (7)0.0010 (6)0.0069 (8)
C2D0.0221 (9)0.0294 (10)0.0208 (11)0.0034 (8)0.0017 (7)0.0098 (9)
C3D0.0273 (10)0.0441 (13)0.0239 (12)0.0073 (9)0.0065 (8)0.0151 (11)
C4D0.0355 (11)0.0419 (13)0.0136 (10)0.0109 (10)0.0048 (8)0.0035 (10)
C5D0.0286 (10)0.0239 (10)0.0167 (10)0.0074 (8)−0.0022 (7)0.0009 (9)
C6D0.0164 (8)0.0199 (9)0.0193 (10)0.0083 (7)0.0012 (7)0.0043 (8)
C7D0.0236 (9)0.0218 (9)0.0247 (11)0.0013 (8)−0.0017 (7)0.0078 (9)
C8D0.0214 (9)0.0268 (10)0.0257 (11)0.0025 (8)0.0035 (8)0.0083 (9)
C9D0.0223 (9)0.0257 (10)0.0197 (10)0.0062 (8)0.0047 (7)0.0079 (9)
C10D0.0392 (12)0.0273 (11)0.0263 (12)0.0011 (9)0.0059 (9)0.0147 (10)
C11D0.0516 (14)0.0262 (11)0.0211 (12)0.0126 (10)0.0021 (9)0.0101 (10)
C12D0.0329 (11)0.0331 (11)0.0190 (11)0.0150 (9)−0.0022 (8)0.0050 (10)
C13D0.0227 (9)0.0242 (10)0.0186 (10)0.0055 (8)0.0007 (7)0.0048 (9)
C14D0.0221 (9)0.0209 (9)0.0138 (9)0.0107 (7)0.0050 (7)0.0075 (8)
C15D0.0199 (8)0.0192 (9)0.0174 (10)0.0031 (7)−0.0021 (7)0.0060 (8)
C16D0.0199 (9)0.0244 (10)0.0224 (10)0.0040 (7)−0.0014 (7)0.0070 (9)
C17D0.0205 (8)0.0255 (10)0.0178 (10)0.0085 (7)0.0024 (7)0.0110 (8)
C18D0.0617 (16)0.0247 (11)0.0344 (14)0.0152 (11)0.0128 (12)0.0063 (11)
Geometric parameters (Å, °) top
N1A—C1A1.420 (2)C12B—H12B0.9500
N1A—C14A1.425 (2)C13B—C14B1.406 (3)
N1A—C15A1.471 (2)C13B—H13B0.9500
N2A—C18A1.481 (3)C15B—C16B1.521 (2)
N2A—C17A1.493 (3)C15B—H15C0.9900
N2A—H2AB0.9200C15B—H15D0.9900
N2A—H2AC0.9200C16B—C17B1.519 (3)
N1B—C1B1.424 (2)C16B—H16C0.9900
N1B—C14B1.429 (2)C16B—H16D0.9900
N1B—C15B1.470 (2)C17B—H17C0.9900
N2B—C18B1.483 (2)C17B—H17D0.9900
N2B—C17B1.493 (2)C18B—H18D0.9800
N2B—H2BB0.9200C18B—H18E0.9800
N2B—H2BC0.9200C18B—H18F0.9800
N1C—C1C1.421 (2)C1C—C2C1.406 (3)
N1C—C14C1.428 (2)C1C—C6C1.411 (3)
N1C—C15C1.471 (2)C2C—C3C1.381 (3)
N2C—C18C1.478 (3)C2C—H2CA0.9500
N2C—C17C1.497 (2)C3C—C4C1.387 (3)
N2C—H2CB0.9200C3C—H3CA0.9500
N2C—H2CC0.9200C4C—C5C1.382 (3)
N1D—C1D1.422 (2)C4C—H4CA0.9500
N1D—C14D1.428 (2)C5C—C6C1.396 (3)
N1D—C15D1.467 (2)C5C—H5CA0.9500
N2D—C18D1.482 (3)C6C—C7C1.532 (3)
N2D—C17D1.489 (2)C7C—C8C1.524 (3)
N2D—H2DB0.9200C7C—H7CA0.9900
N2D—H2DC0.9200C7C—H7CB0.9900
C1A—C2A1.409 (3)C8C—C9C1.501 (3)
C1A—C6A1.411 (3)C8C—H8CA0.9900
C2A—C3A1.369 (3)C8C—H8CB0.9900
C2A—H2AA0.9500C9C—C10C1.390 (3)
C3A—C4A1.386 (3)C9C—C14C1.396 (2)
C3A—H3AA0.9500C10C—C11C1.394 (3)
C4A—C5A1.393 (3)C10C—H10C0.9500
C4A—H4AA0.9500C11C—C12C1.386 (3)
C5A—C6A1.393 (3)C11C—H11C0.9500
C5A—H5AA0.9500C12C—C13C1.386 (3)
C6A—C7A1.525 (3)C12C—H12C0.9500
C7A—C8A1.524 (3)C13C—C14C1.403 (3)
C7A—H7AA0.9900C13C—H13C0.9500
C7A—H7AB0.9900C15C—C16C1.525 (3)
C8A—C9A1.508 (3)C15C—H15E0.9900
C8A—H8AA0.9900C15C—H15F0.9900
C8A—H8AB0.9900C16C—C17C1.519 (3)
C9A—C10A1.391 (3)C16C—H16E0.9900
C9A—C14A1.396 (3)C16C—H16F0.9900
C10A—C11A1.393 (3)C17C—H17E0.9900
C10A—H10A0.9500C17C—H17F0.9900
C11A—C12A1.388 (3)C18C—H18G0.9800
C11A—H11A0.9500C18C—H18H0.9800
C12A—C13A1.387 (3)C18C—H18I0.9800
C12A—H12A0.9500C1D—C6D1.406 (3)
C13A—C14A1.399 (3)C1D—C2D1.408 (3)
C13A—H13A0.9500C2D—C3D1.377 (3)
C15A—C16A1.523 (3)C2D—H2DA0.9500
C15A—H15A0.9900C3D—C4D1.394 (3)
C15A—H15B0.9900C3D—H3DA0.9500
C16A—C17A1.525 (3)C4D—C5D1.383 (3)
C16A—H16A0.9900C4D—H4DA0.9500
C16A—H16B0.9900C5D—C6D1.400 (3)
C17A—H17A0.9900C5D—H5DA0.9500
C17A—H17B0.9900C6D—C7D1.528 (3)
C18A—H18A0.9800C7D—C8D1.528 (3)
C18A—H18B0.9800C7D—H7DA0.9900
C18A—H18C0.9800C7D—H7DB0.9900
C1B—C2B1.395 (3)C8D—C9D1.500 (3)
C1B—C6B1.403 (2)C8D—H8DA0.9900
C2B—C3B1.390 (3)C8D—H8DB0.9900
C2B—H2BA0.9500C9D—C10D1.389 (3)
C3B—C4B1.379 (3)C9D—C14D1.393 (3)
C3B—H3BA0.9500C10D—C11D1.394 (3)
C4B—C5B1.390 (3)C10D—H10D0.9500
C4B—H4BA0.9500C11D—C12D1.390 (3)
C5B—C6B1.392 (3)C11D—H11D0.9500
C5B—H5BA0.9500C12D—C13D1.390 (3)
C6B—C7B1.506 (3)C12D—H12D0.9500
C7B—C8B1.524 (3)C13D—C14D1.402 (2)
C7B—H7BA0.9900C13D—H13D0.9500
C7B—H7BB0.9900C15D—C16D1.531 (3)
C8B—C9B1.524 (3)C15D—H15G0.9900
C8B—H8BA0.9900C15D—H15H0.9900
C8B—H8BB0.9900C16D—C17D1.520 (3)
C9B—C10B1.405 (3)C16D—H16G0.9900
C9B—C14B1.407 (3)C16D—H16H0.9900
C10B—C11B1.383 (3)C17D—H17G0.9900
C10B—H10B0.9500C17D—H17H0.9900
C11B—C12B1.377 (3)C18D—H18J0.9800
C11B—H11B0.9500C18D—H18K0.9800
C12B—C13B1.386 (3)C18D—H18L0.9800
C1A—N1A—C14A117.77 (14)C17B—C16B—C15B113.78 (15)
C1A—N1A—C15A118.55 (15)C17B—C16B—H16C108.8
C14A—N1A—C15A117.12 (15)C15B—C16B—H16C108.8
C18A—N2A—C17A112.49 (16)C17B—C16B—H16D108.8
C18A—N2A—H2AB109.1C15B—C16B—H16D108.8
C17A—N2A—H2AB109.1H16C—C16B—H16D107.7
C18A—N2A—H2AC109.1N2B—C17B—C16B112.18 (16)
C17A—N2A—H2AC109.1N2B—C17B—H17C109.2
H2AB—N2A—H2AC107.8C16B—C17B—H17C109.2
C1B—N1B—C14B117.82 (14)N2B—C17B—H17D109.2
C1B—N1B—C15B115.96 (15)C16B—C17B—H17D109.2
C14B—N1B—C15B119.30 (15)H17C—C17B—H17D107.9
C18B—N2B—C17B112.37 (16)N2B—C18B—H18D109.5
C18B—N2B—H2BB109.1N2B—C18B—H18E109.5
C17B—N2B—H2BB109.1H18D—C18B—H18E109.5
C18B—N2B—H2BC109.1N2B—C18B—H18F109.5
C17B—N2B—H2BC109.1H18D—C18B—H18F109.5
H2BB—N2B—H2BC107.9H18E—C18B—H18F109.5
C1C—N1C—C14C118.46 (14)C2C—C1C—C6C118.56 (17)
C1C—N1C—C15C119.45 (15)C2C—C1C—N1C119.15 (16)
C14C—N1C—C15C116.07 (15)C6C—C1C—N1C122.28 (16)
C18C—N2C—C17C113.03 (16)C3C—C2C—C1C121.42 (19)
C18C—N2C—H2CB109.0C3C—C2C—H2CA119.3
C17C—N2C—H2CB109.0C1C—C2C—H2CA119.3
C18C—N2C—H2CC109.0C2C—C3C—C4C120.6 (2)
C17C—N2C—H2CC109.0C2C—C3C—H3CA119.7
H2CB—N2C—H2CC107.8C4C—C3C—H3CA119.7
C1D—N1D—C14D118.17 (14)C5C—C4C—C3C118.02 (19)
C1D—N1D—C15D118.84 (15)C5C—C4C—H4CA121.0
C14D—N1D—C15D116.60 (15)C3C—C4C—H4CA121.0
C18D—N2D—C17D113.21 (17)C4C—C5C—C6C123.36 (19)
C18D—N2D—H2DB108.9C4C—C5C—H5CA118.3
C17D—N2D—H2DB108.9C6C—C5C—H5CA118.3
C18D—N2D—H2DC108.9C5C—C6C—C1C117.98 (18)
C17D—N2D—H2DC108.9C5C—C6C—C7C116.04 (17)
H2DB—N2D—H2DC107.7C1C—C6C—C7C125.95 (17)
C2A—C1A—C6A118.40 (18)C8C—C7C—C6C117.86 (16)
C2A—C1A—N1A119.65 (17)C8C—C7C—H7CA107.8
C6A—C1A—N1A121.95 (16)C6C—C7C—H7CA107.8
C3A—C2A—C1A122.1 (2)C8C—C7C—H7CB107.8
C3A—C2A—H2AA119.0C6C—C7C—H7CB107.8
C1A—C2A—H2AA119.0H7CA—C7C—H7CB107.2
C2A—C3A—C4A120.3 (2)C9C—C8C—C7C111.71 (15)
C2A—C3A—H3AA119.9C9C—C8C—H8CA109.3
C4A—C3A—H3AA119.9C7C—C8C—H8CA109.3
C3A—C4A—C5A118.1 (2)C9C—C8C—H8CB109.3
C3A—C4A—H4AA120.9C7C—C8C—H8CB109.3
C5A—C4A—H4AA120.9H8CA—C8C—H8CB107.9
C4A—C5A—C6A123.1 (2)C10C—C9C—C14C118.87 (17)
C4A—C5A—H5AA118.4C10C—C9C—C8C122.76 (17)
C6A—C5A—H5AA118.4C14C—C9C—C8C118.36 (17)
C5A—C6A—C1A117.93 (17)C9C—C10C—C11C121.05 (19)
C5A—C6A—C7A116.16 (17)C9C—C10C—H10C119.5
C1A—C6A—C7A125.90 (18)C11C—C10C—H10C119.5
C8A—C7A—C6A118.24 (16)C12C—C11C—C10C119.80 (19)
C8A—C7A—H7AA107.8C12C—C11C—H11C120.1
C6A—C7A—H7AA107.8C10C—C11C—H11C120.1
C8A—C7A—H7AB107.8C13C—C12C—C11C119.95 (18)
C6A—C7A—H7AB107.8C13C—C12C—H12C120.0
H7AA—C7A—H7AB107.1C11C—C12C—H12C120.0
C9A—C8A—C7A111.64 (16)C12C—C13C—C14C120.19 (18)
C9A—C8A—H8AA109.3C12C—C13C—H13C119.9
C7A—C8A—H8AA109.3C14C—C13C—H13C119.9
C9A—C8A—H8AB109.3C9C—C14C—C13C120.12 (17)
C7A—C8A—H8AB109.3C9C—C14C—N1C118.27 (16)
H8AA—C8A—H8AB108.0C13C—C14C—N1C121.59 (16)
C10A—C9A—C14A119.11 (17)N1C—C15C—C16C110.18 (15)
C10A—C9A—C8A123.12 (17)N1C—C15C—H15E109.6
C14A—C9A—C8A117.78 (17)C16C—C15C—H15E109.6
C9A—C10A—C11A121.01 (19)N1C—C15C—H15F109.6
C9A—C10A—H10A119.5C16C—C15C—H15F109.6
C11A—C10A—H10A119.5H15E—C15C—H15F108.1
C12A—C11A—C10A119.6 (2)C17C—C16C—C15C113.63 (15)
C12A—C11A—H11A120.2C17C—C16C—H16E108.8
C10A—C11A—H11A120.2C15C—C16C—H16E108.8
C13A—C12A—C11A120.12 (18)C17C—C16C—H16F108.8
C13A—C12A—H12A119.9C15C—C16C—H16F108.8
C11A—C12A—H12A119.9H16E—C16C—H16F107.7
C12A—C13A—C14A120.18 (18)N2C—C17C—C16C112.27 (16)
C12A—C13A—H13A119.9N2C—C17C—H17E109.2
C14A—C13A—H13A119.9C16C—C17C—H17E109.2
C9A—C14A—C13A119.99 (18)N2C—C17C—H17F109.2
C9A—C14A—N1A118.42 (16)C16C—C17C—H17F109.2
C13A—C14A—N1A121.56 (16)H17E—C17C—H17F107.9
N1A—C15A—C16A110.20 (14)N2C—C18C—H18G109.5
N1A—C15A—H15A109.6N2C—C18C—H18H109.5
C16A—C15A—H15A109.6H18G—C18C—H18H109.5
N1A—C15A—H15B109.6N2C—C18C—H18I109.5
C16A—C15A—H15B109.6H18G—C18C—H18I109.5
H15A—C15A—H15B108.1H18H—C18C—H18I109.5
C15A—C16A—C17A114.88 (15)C6D—C1D—C2D118.84 (17)
C15A—C16A—H16A108.5C6D—C1D—N1D122.21 (16)
C17A—C16A—H16A108.5C2D—C1D—N1D118.95 (17)
C15A—C16A—H16B108.5C3D—C2D—C1D121.6 (2)
C17A—C16A—H16B108.5C3D—C2D—H2DA119.2
H16A—C16A—H16B107.5C1D—C2D—H2DA119.2
N2A—C17A—C16A111.45 (16)C2D—C3D—C4D120.0 (2)
N2A—C17A—H17A109.3C2D—C3D—H3DA120.0
C16A—C17A—H17A109.3C4D—C3D—H3DA120.0
N2A—C17A—H17B109.3C5D—C4D—C3D118.64 (19)
C16A—C17A—H17B109.3C5D—C4D—H4DA120.7
H17A—C17A—H17B108.0C3D—C4D—H4DA120.7
N2A—C18A—H18A109.5C4D—C5D—C6D122.69 (19)
N2A—C18A—H18B109.5C4D—C5D—H5DA118.7
H18A—C18A—H18B109.5C6D—C5D—H5DA118.7
N2A—C18A—H18C109.5C5D—C6D—C1D118.16 (18)
H18A—C18A—H18C109.5C5D—C6D—C7D115.69 (17)
H18B—C18A—H18C109.5C1D—C6D—C7D126.14 (17)
C2B—C1B—C6B119.63 (18)C6D—C7D—C8D118.03 (17)
C2B—C1B—N1B122.30 (17)C6D—C7D—H7DA107.8
C6B—C1B—N1B118.05 (15)C8D—C7D—H7DA107.8
C3B—C2B—C1B120.78 (19)C6D—C7D—H7DB107.8
C3B—C2B—H2BA119.6C8D—C7D—H7DB107.8
C1B—C2B—H2BA119.6H7DA—C7D—H7DB107.1
C4B—C3B—C2B119.80 (18)C9D—C8D—C7D111.84 (15)
C4B—C3B—H3BA120.1C9D—C8D—H8DA109.2
C2B—C3B—H3BA120.1C7D—C8D—H8DA109.2
C3B—C4B—C5B119.8 (2)C9D—C8D—H8DB109.2
C3B—C4B—H4BA120.1C7D—C8D—H8DB109.2
C5B—C4B—H4BA120.1H8DA—C8D—H8DB107.9
C4B—C5B—C6B121.41 (19)C10D—C9D—C14D118.83 (18)
C4B—C5B—H5BA119.3C10D—C9D—C8D122.82 (18)
C6B—C5B—H5BA119.3C14D—C9D—C8D118.36 (17)
C5B—C6B—C1B118.61 (17)C9D—C10D—C11D121.26 (19)
C5B—C6B—C7B123.12 (18)C9D—C10D—H10D119.4
C1B—C6B—C7B118.27 (17)C11D—C10D—H10D119.4
C6B—C7B—C8B111.72 (16)C12D—C11D—C10D119.54 (19)
C6B—C7B—H7BA109.3C12D—C11D—H11D120.2
C8B—C7B—H7BA109.3C10D—C11D—H11D120.2
C6B—C7B—H7BB109.3C11D—C12D—C13D120.05 (19)
C8B—C7B—H7BB109.3C11D—C12D—H12D120.0
H7BA—C7B—H7BB107.9C13D—C12D—H12D120.0
C9B—C8B—C7B117.28 (16)C12D—C13D—C14D119.87 (18)
C9B—C8B—H8BA108.0C12D—C13D—H13D120.1
C7B—C8B—H8BA108.0C14D—C13D—H13D120.1
C9B—C8B—H8BB108.0C9D—C14D—C13D120.44 (17)
C7B—C8B—H8BB108.0C9D—C14D—N1D118.45 (16)
H8BA—C8B—H8BB107.2C13D—C14D—N1D121.10 (16)
C10B—C9B—C14B117.99 (18)N1D—C15D—C16D110.32 (15)
C10B—C9B—C8B115.28 (17)N1D—C15D—H15G109.6
C14B—C9B—C8B126.71 (17)C16D—C15D—H15G109.6
C11B—C10B—C9B122.8 (2)N1D—C15D—H15H109.6
C11B—C10B—H10B118.6C16D—C15D—H15H109.6
C9B—C10B—H10B118.6H15G—C15D—H15H108.1
C12B—C11B—C10B118.6 (2)C17D—C16D—C15D114.46 (15)
C12B—C11B—H11B120.7C17D—C16D—H16G108.6
C10B—C11B—H11B120.7C15D—C16D—H16G108.6
C11B—C12B—C13B120.49 (19)C17D—C16D—H16H108.6
C11B—C12B—H12B119.8C15D—C16D—H16H108.6
C13B—C12B—H12B119.8H16G—C16D—H16H107.6
C12B—C13B—C14B121.35 (19)N2D—C17D—C16D111.78 (16)
C12B—C13B—H13B119.3N2D—C17D—H17G109.3
C14B—C13B—H13B119.3C16D—C17D—H17G109.3
C13B—C14B—C9B118.67 (18)N2D—C17D—H17H109.3
C13B—C14B—N1B119.09 (17)C16D—C17D—H17H109.3
C9B—C14B—N1B122.24 (16)H17G—C17D—H17H107.9
N1B—C15B—C16B110.75 (14)N2D—C18D—H18J109.5
N1B—C15B—H15C109.5N2D—C18D—H18K109.5
C16B—C15B—H15C109.5H18J—C18D—H18K109.5
N1B—C15B—H15D109.5N2D—C18D—H18L109.5
C16B—C15B—H15D109.5H18J—C18D—H18L109.5
H15C—C15B—H15D108.1H18K—C18D—H18L109.5
C14A—N1A—C1A—C2A−125.96 (18)C14C—N1C—C1C—C2C129.01 (18)
C15A—N1A—C1A—C2A24.9 (2)C15C—N1C—C1C—C2C−22.6 (2)
C14A—N1A—C1A—C6A53.9 (2)C14C—N1C—C1C—C6C−52.1 (2)
C15A—N1A—C1A—C6A−155.25 (16)C15C—N1C—C1C—C6C156.23 (16)
C6A—C1A—C2A—C3A−2.3 (3)C6C—C1C—C2C—C3C3.1 (3)
N1A—C1A—C2A—C3A177.58 (18)N1C—C1C—C2C—C3C−178.01 (17)
C1A—C2A—C3A—C4A1.7 (3)C1C—C2C—C3C—C4C−0.8 (3)
C2A—C3A—C4A—C5A−0.3 (3)C2C—C3C—C4C—C5C−1.7 (3)
C3A—C4A—C5A—C6A−0.3 (3)C3C—C4C—C5C—C6C2.1 (3)
C4A—C5A—C6A—C1A−0.4 (3)C4C—C5C—C6C—C1C0.1 (3)
C4A—C5A—C6A—C7A178.84 (19)C4C—C5C—C6C—C7C−178.10 (18)
C2A—C1A—C6A—C5A1.6 (3)C2C—C1C—C6C—C5C−2.7 (2)
N1A—C1A—C6A—C5A−178.26 (17)N1C—C1C—C6C—C5C178.46 (16)
C2A—C1A—C6A—C7A−177.52 (18)C2C—C1C—C6C—C7C175.35 (17)
N1A—C1A—C6A—C7A2.6 (3)N1C—C1C—C6C—C7C−3.5 (3)
C5A—C6A—C7A—C8A−175.18 (17)C5C—C6C—C7C—C8C173.64 (17)
C1A—C6A—C7A—C8A4.0 (3)C1C—C6C—C7C—C8C−4.4 (3)
C6A—C7A—C8A—C9A−60.4 (2)C6C—C7C—C8C—C9C61.0 (2)
C7A—C8A—C9A—C10A−109.5 (2)C7C—C8C—C9C—C10C111.0 (2)
C7A—C8A—C9A—C14A70.0 (2)C7C—C8C—C9C—C14C−70.1 (2)
C14A—C9A—C10A—C11A1.0 (3)C14C—C9C—C10C—C11C0.3 (3)
C8A—C9A—C10A—C11A−179.4 (2)C8C—C9C—C10C—C11C179.19 (18)
C9A—C10A—C11A—C12A−1.4 (3)C9C—C10C—C11C—C12C0.9 (3)
C10A—C11A—C12A—C13A1.3 (3)C10C—C11C—C12C—C13C−1.0 (3)
C11A—C12A—C13A—C14A−0.7 (3)C11C—C12C—C13C—C14C0.0 (3)
C10A—C9A—C14A—C13A−0.5 (3)C10C—C9C—C14C—C13C−1.3 (3)
C8A—C9A—C14A—C13A179.97 (18)C8C—C9C—C14C—C13C179.71 (17)
C10A—C9A—C14A—N1A−178.46 (17)C10C—C9C—C14C—N1C177.03 (16)
C8A—C9A—C14A—N1A2.0 (3)C8C—C9C—C14C—N1C−1.9 (2)
C12A—C13A—C14A—C9A0.3 (3)C12C—C13C—C14C—C9C1.2 (3)
C12A—C13A—C14A—N1A178.24 (17)C12C—C13C—C14C—N1C−177.09 (17)
C1A—N1A—C14A—C9A−73.3 (2)C1C—N1C—C14C—C9C72.2 (2)
C15A—N1A—C14A—C9A135.44 (17)C15C—N1C—C14C—C9C−135.26 (17)
C1A—N1A—C14A—C13A108.7 (2)C1C—N1C—C14C—C13C−109.53 (19)
C15A—N1A—C14A—C13A−42.5 (2)C15C—N1C—C14C—C13C43.1 (2)
C1A—N1A—C15A—C16A66.8 (2)C1C—N1C—C15C—C16C−70.4 (2)
C14A—N1A—C15A—C16A−142.22 (16)C14C—N1C—C15C—C16C137.35 (16)
N1A—C15A—C16A—C17A−177.75 (16)N1C—C15C—C16C—C17C177.12 (16)
C18A—N2A—C17A—C16A−165.59 (16)C18C—N2C—C17C—C16C173.74 (16)
C15A—C16A—C17A—N2A−65.2 (2)C15C—C16C—C17C—N2C63.4 (2)
C14B—N1B—C1B—C2B−109.8 (2)C14D—N1D—C1D—C6D52.6 (2)
C15B—N1B—C1B—C2B41.0 (2)C15D—N1D—C1D—C6D−156.35 (16)
C14B—N1B—C1B—C6B71.6 (2)C14D—N1D—C1D—C2D−127.45 (18)
C15B—N1B—C1B—C6B−137.62 (17)C15D—N1D—C1D—C2D23.6 (2)
C6B—C1B—C2B—C3B0.2 (3)C6D—C1D—C2D—C3D−2.4 (3)
N1B—C1B—C2B—C3B−178.37 (17)N1D—C1D—C2D—C3D177.64 (17)
C1B—C2B—C3B—C4B0.9 (3)C1D—C2D—C3D—C4D0.3 (3)
C2B—C3B—C4B—C5B−1.8 (3)C2D—C3D—C4D—C5D1.7 (3)
C3B—C4B—C5B—C6B1.6 (3)C3D—C4D—C5D—C6D−1.7 (3)
C4B—C5B—C6B—C1B−0.5 (3)C4D—C5D—C6D—C1D−0.5 (3)
C4B—C5B—C6B—C7B178.7 (2)C4D—C5D—C6D—C7D178.58 (18)
C2B—C1B—C6B—C5B−0.4 (3)C2D—C1D—C6D—C5D2.5 (2)
N1B—C1B—C6B—C5B178.22 (17)N1D—C1D—C6D—C5D−177.62 (15)
C2B—C1B—C6B—C7B−179.63 (18)C2D—C1D—C6D—C7D−176.46 (17)
N1B—C1B—C6B—C7B−1.0 (3)N1D—C1D—C6D—C7D3.4 (3)
C5B—C6B—C7B—C8B109.6 (2)C5D—C6D—C7D—C8D−175.50 (16)
C1B—C6B—C7B—C8B−71.2 (2)C1D—C6D—C7D—C8D3.5 (3)
C6B—C7B—C8B—C9B59.9 (2)C6D—C7D—C8D—C9D−59.9 (2)
C7B—C8B—C9B—C10B176.24 (17)C7D—C8D—C9D—C10D−109.9 (2)
C7B—C8B—C9B—C14B−2.1 (3)C7D—C8D—C9D—C14D69.8 (2)
C14B—C9B—C10B—C11B1.8 (3)C14D—C9D—C10D—C11D1.2 (3)
C8B—C9B—C10B—C11B−176.79 (19)C8D—C9D—C10D—C11D−179.01 (19)
C9B—C10B—C11B—C12B0.4 (3)C9D—C10D—C11D—C12D−1.7 (3)
C10B—C11B—C12B—C13B−0.6 (3)C10D—C11D—C12D—C13D1.0 (3)
C11B—C12B—C13B—C14B−1.3 (3)C11D—C12D—C13D—C14D0.0 (3)
C12B—C13B—C14B—C9B3.5 (3)C10D—C9D—C14D—C13D−0.2 (3)
C12B—C13B—C14B—N1B−176.75 (17)C8D—C9D—C14D—C13D−179.94 (17)
C10B—C9B—C14B—C13B−3.6 (3)C10D—C9D—C14D—N1D−178.64 (17)
C8B—C9B—C14B—C13B174.75 (18)C8D—C9D—C14D—N1D1.6 (3)
C10B—C9B—C14B—N1B176.65 (17)C12D—C13D—C14D—C9D−0.5 (3)
C8B—C9B—C14B—N1B−5.0 (3)C12D—C13D—C14D—N1D177.96 (17)
C1B—N1B—C14B—C13B128.10 (18)C1D—N1D—C14D—C9D−72.2 (2)
C15B—N1B—C14B—C13B−21.6 (2)C15D—N1D—C14D—C9D136.13 (18)
C1B—N1B—C14B—C9B−52.2 (2)C1D—N1D—C14D—C13D109.35 (19)
C15B—N1B—C14B—C9B158.11 (16)C15D—N1D—C14D—C13D−42.3 (2)
C1B—N1B—C15B—C16B140.25 (16)C1D—N1D—C15D—C16D67.2 (2)
C14B—N1B—C15B—C16B−69.5 (2)C14D—N1D—C15D—C16D−141.31 (16)
N1B—C15B—C16B—C17B178.11 (16)N1D—C15D—C16D—C17D−176.53 (16)
C18B—N2B—C17B—C16B173.14 (16)C18D—N2D—C17D—C16D−166.99 (16)
C15B—C16B—C17B—N2B63.2 (2)C15D—C16D—C17D—N2D−64.0 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2A—H2AB···Cl3i0.922.223.1186 (16)165
N2A—H2AC···Cl30.922.173.0811 (17)169
N2B—H2BB···Cl10.922.203.1027 (16)168
N2B—H2BC···Cl40.922.203.1014 (16)165
N2C—H2CB···Cl10.922.203.1069 (16)167
N2C—H2CC···Cl40.922.213.1065 (16)166
N2D—H2DB···Cl20.922.223.1176 (16)166
N2D—H2DC···Cl2ii0.922.183.0859 (16)168
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2A—H2AB···Cl3i0.922.223.1186 (16)165
N2A—H2AC···Cl30.922.173.0811 (17)169
N2B—H2BB···Cl10.922.203.1027 (16)168
N2B—H2BC···Cl40.922.203.1014 (16)165
N2C—H2CB···Cl10.922.203.1069 (16)167
N2C—H2CC···Cl40.922.213.1065 (16)166
N2D—H2DB···Cl20.922.223.1176 (16)166
N2D—H2DC···Cl2ii0.922.183.0859 (16)168
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2.
Acknowledgements top

QNMHA thanks the University of Mysore for use of its research facilities. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

references
References top

Ahmed, S. A., Silwadi, M. F. & Khatoon, B. A. (2002). J. Pharm. Biomed. Anal. 28, 501–507.

Bindya, S., Wong, W.-T., Ashok, M. A., Yathirajan, H. S. & Rathore, R. S. (2007). Acta Cryst. C63, o546–o548.

Butcher, R. J., Jasinski, J. P., Yathirajan, H. S., Bindya, S. & Narayana, B. (2007). Acta Cryst. E63, o3291–o3292.

Cohen, M. D., Finberg, J., Dibner-Dunlap, M., Yuih, S. N. & Thames, M. D. (1990). Am. J. Physiol. Regul. Integr. Comp. Physiol. 258, 876–882.

Deupree, J. D., Montogomery, M. D. & Bylund, D. B. (2007). Eur. J. Pharmacol. 576, 55–60.

Harrison, W. T. A., Swamy, M. T., Nagaraja, P., Yathirajan, H. S. & Narayana, B. (2007). Acta Cryst. E63, o3892.

Klein, C. L., Banks, T. A. & Rouselle, D. (1991). Acta Cryst. C47, 1478–1480.

Klein, C. L., Lear, J., O'Rourke, S., Williams, S. & Liang, L. (1994). J. Pharm. Sci. 83, 1253–1256.

Nagaraja, P., Silwadi, M. F. & Akheel Ahmed, S. (2000). Mikrochim. Acta, 135, 185–189.

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

Portalone, G., Colapietro, M., Bindya, S., Ashok, M. A. & Yathirajan, H. S. (2007). Acta Cryst. E63, o746–o747.

Post, M. L., Kennard, O. & Horn, A. S. (1975). Acta Cryst. B31, 1008–1013.

Schmidt, J. R. & Polik, W. F. (2007). WebMO Pro. WebMO, LLC: Holland, MI, USA, ; available from http://www.webmo.net.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Swamy, M. T., Ashok, M. A., Yathirajan, H. S., Narayana, B. & Bolte, M. (2007). Acta Cryst. E63, o4919.