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Acta Cryst. (2008). E64, o889    [ doi:10.1107/S1600536808010490 ]

N-(2,4-Dinitrophenyl)dehydroabietylamine

F. Qiu, M. Hong, D. Jiang, J. Zhu and L. L. Huang

Abstract top

In the crystal structure of the title compound, C26H33N3O4, there are two crystallographically independent molecules. The two cyclohexane rings are trans-fused; the ring neighboring the phenyl group is in a half-chair conformation and the other is in a chair conformation. The two nitro groups and the benzene ring of the dinitrophenyl group are almost coplanar. Intramolecular N-H...O hydrogen bonds and weak intermolecular C-H...O hydrogen bonds are observed.

Comment top

Chiral ionic liquids have potential applications in chiral recognition and asymmetric synthesis (Baudequin et al., 2005). One way to get chiral ionic liquids is from chiral amine through Marazano's route (Patrascu et al., 2004; Ou & Huang, 2006). Dehydroabietylamine which acts as a resolving agent for carboxylic acids (Gottstein & Cheney, 1965), has three chiral centres, and is inexpensive and relatively nontoxic. The title compound, (I), was an unexpected product obtained in an attempt to synthesize a chiral imidazolium ionic liquid via the reaction of 1-(2,4-dinitrophenyl)-3-methylimidazolium chloride with dehydroabietylamine. In this work, we describe the synthesis and crystal structure of the title compound.

As shown in Fig. 1, the asymmetric unit of (I) contains two independent molecules. Each molecule has three chiral centers. In (I), there exists four crystallographically distinct six-membered rings. Two cyclohexane rings form a trans ring junction with a classical chair and a half-chair conformation, and two methyl groups in axial positions (Pan et al., 2005; Jiang et al., 2007). Two nitro groups and the benzene ring in the substituted aryl group are almost coplanar. Intramolecular N—H···O hydrogen bonds contribute strongly to the stability of the molecular configuration (Fig. 2 and Table 1). Further analysis of the crystal packing suggests that there are some weak C—H···O interactions stabilizing the packing of (I).

Related literature top

For related literature, see: Baudequin et al. (2005); Gottstein & Cheney (1965); Jiang et al. (2007); Ou & Huang (2006); Pan et al. (2005); Patrascu et al. (2004).

Experimental top

To 1-(2,4-dinitrophenyl)-3-methylimidazolium chloride (3.0 g, 10.5 mmol) suspended in n-butanol (50 ml) was added a solution of dehydroabietylamine (3.3 g, 11.5 mmol) in n-butanol (10 ml) and the mixture was refluxed for 24 h. Removal of solvent under reduced pressure left a residue, which was further purified by column chromatography (n-hexane/ethyl acetate as eluent) and then recrystallized from methanol to give the title compound (yield 35.5%, m.p. 408–409 K).

Refinement top

H atoms attached to C atoms were positioned geometrically (C—H = 0.93–0.98 Å) and were refined as riding, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The coordinates of the H atoms bonded to N were refined with Uiso(H) = 1.2Ueq(N), giving the N—H distance of 0.86 (5) Å. In the absence of significant anomalous scattering effects, Friedel pairs have been merged.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 35% probability displacement ellipsoids and the atom-numbering schemes.
[Figure 2] Fig. 2. A packing diagram of the title compound, showing hydrogen bonds drawn as dashed lines.
N-(2,4-Dinitrophenyl)dehydroabietylamine top
Crystal data top
C26H33N3O4F000 = 968
Mr = 451.55Dx = 1.249 Mg m−3
Monoclinic, P21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1357 reflections
a = 14.119 (7) Åθ = 2.9–18.1º
b = 23.574 (12) ŵ = 0.09 mm−1
c = 7.309 (4) ÅT = 291 (2) K
β = 99.191 (9)ºBlock, light-yellow
V = 2402 (2) Å30.30 × 0.26 × 0.24 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer		6027 independent reflections
Radiation source: sealed tube4715 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.046
T = 291(2) Kθmax = 28.6º
φ and ω scansθmin = 1.7º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −16→18
Tmin = 0.98, Tmax = 0.98k = −31→31
15350 measured reflectionsl = −9→9
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)] = 0.062H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.139  w = 1/[σ2(Fo2) + (0.07P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
6027 reflectionsΔρmax = 0.19 e Å−3
609 parametersΔρmin = −0.19 e Å−3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C26H33N3O4V = 2402 (2) Å3
Mr = 451.55Z = 4
Monoclinic, P21Mo Kα
a = 14.119 (7) ŵ = 0.09 mm−1
b = 23.574 (12) ÅT = 291 (2) K
c = 7.309 (4) Å0.30 × 0.26 × 0.24 mm
β = 99.191 (9)º
Data collection top
Bruker SMART APEX CCD
diffractometer		6027 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		4715 reflections with I > 2σ(I)
Tmin = 0.98, Tmax = 0.98Rint = 0.046
15350 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.062H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.139Δρmax = 0.19 e Å−3
S = 1.07Δρmin = −0.19 e Å−3
6027 reflectionsAbsolute structure: ?
609 parametersFlack parameter: ?
1 restraintRogers 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*/Ueq
C10.6051 (3)1.03496 (15)0.3284 (6)0.0432 (8)
C20.6497 (3)1.01296 (18)0.1815 (5)0.0433 (8)
H20.65740.97380.17630.052*
C30.6826 (3)1.0453 (2)0.0451 (6)0.0539 (10)
H30.71011.0292−0.05010.065*
C40.6711 (3)1.1052 (2)0.0627 (7)0.0562 (11)
C50.6347 (3)1.12950 (17)0.2041 (6)0.0481 (9)
H50.63081.16880.21310.058*
C60.6036 (3)1.09476 (15)0.3349 (5)0.0419 (8)
C70.5823 (3)0.93895 (15)0.4645 (6)0.0462 (9)
H7A0.64550.92860.52850.055*
H7B0.57370.92150.34280.055*
C80.5050 (2)0.91540 (12)0.5747 (5)0.0331 (7)
C90.5037 (3)0.94785 (13)0.7600 (5)0.0386 (8)
H9A0.56940.95270.82110.046*
H9B0.47730.98540.73090.046*
C100.4483 (3)0.92050 (15)0.8925 (6)0.0447 (9)
H10A0.38170.91660.83590.054*
H10B0.45090.94391.00240.054*
C110.4910 (3)0.86223 (14)0.9458 (5)0.0415 (8)
H11A0.45540.84451.03360.050*
H11B0.55700.86661.00570.050*
C120.4876 (3)0.82217 (15)0.7685 (5)0.0381 (7)
C130.5412 (3)0.76731 (14)0.8357 (5)0.0357 (7)
C140.5280 (2)0.74107 (13)0.9926 (5)0.0344 (7)
H140.48510.75701.06230.041*
C150.5761 (3)0.69012 (16)1.0579 (5)0.0459 (8)
H150.56500.67371.16830.055*
C160.6404 (3)0.66476 (14)0.9544 (5)0.0398 (8)
C170.6516 (3)0.69130 (14)0.7860 (5)0.0407 (8)
H170.69230.67520.71220.049*
C180.6025 (2)0.74134 (14)0.7281 (5)0.0352 (7)
C190.6249 (3)0.76646 (14)0.5425 (5)0.0390 (8)
H19A0.68920.78220.56200.047*
H19B0.62240.73650.45100.047*
C200.5532 (3)0.81258 (14)0.4705 (5)0.0383 (8)
H20A0.49140.79580.42360.046*
H20B0.57520.83310.37010.046*
C210.5437 (3)0.85369 (13)0.6321 (5)0.0331 (7)
H210.60890.85900.69940.040*
C220.4086 (3)0.91669 (18)0.4435 (6)0.0513 (10)
H22A0.35730.92000.51470.077*
H22B0.40100.88230.37230.077*
H22C0.40720.94860.36150.077*
C230.3848 (3)0.80579 (14)0.7005 (5)0.0421 (8)
H23A0.37970.78960.57880.063*
H23B0.34480.83890.69570.063*
H23C0.36440.77850.78360.063*
C240.6938 (3)0.61086 (15)1.0142 (6)0.0420 (8)
H240.74510.60570.93990.050*
C250.6235 (3)0.56052 (16)0.9783 (6)0.0513 (10)
H25A0.65830.52680.95710.077*
H25B0.57640.56840.87130.077*
H25C0.59210.55511.08420.077*
C260.7371 (3)0.61064 (15)1.2165 (6)0.0462 (9)
H26A0.68790.60311.29010.069*
H26B0.76550.64701.24990.069*
H26C0.78540.58171.23860.069*
C270.8660 (3)0.30147 (16)0.5585 (5)0.0461 (9)
C280.8144 (2)0.28052 (15)0.6931 (5)0.0364 (7)
H280.79320.24310.68480.044*
C290.7940 (3)0.31439 (17)0.8397 (6)0.0476 (9)
H290.76460.29910.93380.057*
C300.8189 (3)0.37176 (18)0.8405 (5)0.0461 (9)
C310.8630 (3)0.39573 (17)0.7035 (6)0.0481 (9)
H310.87530.43450.70410.058*
C320.8884 (3)0.36200 (17)0.5670 (6)0.0496 (10)
C330.8782 (3)0.20752 (18)0.4190 (7)0.0526 (10)
H33A0.81870.19870.33780.063*
H33B0.87370.19280.54130.063*
C340.9638 (2)0.17850 (16)0.3441 (5)0.0394 (8)
C350.9616 (3)0.2017 (2)0.1400 (6)0.0533 (10)
H35A0.89590.20090.07590.064*
H35B0.98250.24090.14670.064*
C361.0223 (3)0.16940 (16)0.0306 (6)0.0451 (9)
H36A1.08860.17160.09080.054*
H36B1.01810.1864−0.09130.054*
C370.9912 (3)0.10552 (17)0.0095 (6)0.0451 (9)
H37A0.92660.1031−0.05930.054*
H37B1.03380.0855−0.06010.054*
C380.9944 (3)0.07674 (16)0.2038 (5)0.0410 (8)
C390.9476 (3)0.01943 (17)0.1764 (6)0.0462 (9)
C400.9525 (3)−0.01538 (18)0.0191 (6)0.0487 (9)
H400.9807−0.0001−0.07650.058*
C410.9189 (3)−0.06933 (18)−0.0008 (6)0.0527 (10)
H410.9299−0.0920−0.09950.063*
C420.8665 (3)−0.08959 (17)0.1350 (6)0.0495 (9)
C430.8643 (3)−0.05987 (15)0.2910 (6)0.0469 (9)
H430.8387−0.07680.38710.056*
C440.8990 (3)−0.00449 (16)0.3140 (6)0.0454 (9)
C450.8833 (3)0.02884 (19)0.4823 (5)0.0504 (9)
H45A0.81570.03820.47100.060*
H45B0.89950.00500.59100.060*
C460.9406 (3)0.08257 (18)0.5118 (5)0.0472 (9)
H46A1.00630.07380.56590.057*
H46B0.91370.10700.59710.057*
C470.9395 (3)0.11368 (17)0.3245 (5)0.0414 (8)
H470.87250.11220.26350.050*
C481.0574 (3)0.19114 (17)0.4684 (6)0.0478 (9)
H48A1.06320.23130.48920.072*
H48B1.10980.17810.41020.072*
H48C1.05890.17200.58470.072*
C491.1003 (3)0.06585 (17)0.2926 (6)0.0477 (9)
H49A1.10220.04900.41270.071*
H49B1.13460.10120.30490.071*
H49C1.12970.04070.21500.071*
C500.8210 (3)−0.15026 (17)0.1030 (6)0.0457 (9)
H500.7520−0.14750.10650.055*
C510.8665 (3)−0.18691 (18)0.2626 (6)0.0485 (9)
H51A0.8173−0.20520.31770.073*
H51B0.9050−0.16370.35370.073*
H51C0.9063−0.21510.21800.073*
C520.8352 (3)−0.18168 (19)−0.0710 (5)0.0524 (10)
H52A0.8988−0.1972−0.05520.079*
H52B0.8266−0.1559−0.17400.079*
H52C0.7891−0.2118−0.09410.079*
N10.7052 (2)1.13979 (16)−0.0758 (5)0.0526 (9)
N20.5607 (2)1.12477 (13)0.4765 (5)0.0467 (8)
N30.5767 (3)1.00406 (13)0.4424 (5)0.0487 (8)
H3A0.549 (3)1.021 (2)0.523 (7)0.058*
N40.7997 (2)0.40656 (16)0.9895 (6)0.0549 (9)
N50.9317 (3)0.39006 (16)0.4270 (6)0.0568 (9)
N60.8912 (2)0.26788 (15)0.4290 (5)0.0478 (8)
H60.918 (3)0.284 (2)0.344 (7)0.057*
O10.7368 (2)1.11758 (13)−0.2038 (4)0.0527 (7)
O20.70301 (19)1.19145 (13)−0.0571 (4)0.0495 (7)
O30.57835 (17)1.17599 (9)0.4971 (4)0.0389 (5)
O40.5187 (2)1.09936 (10)0.5818 (4)0.0450 (6)
O50.7625 (2)0.38555 (12)1.1176 (4)0.0506 (7)
O60.8212 (2)0.45609 (12)0.9977 (4)0.0512 (7)
O70.93068 (18)0.44089 (12)0.4172 (4)0.0479 (6)
O80.9785 (2)0.35937 (12)0.3293 (4)0.0494 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.055 (2)0.0282 (17)0.048 (2)−0.0011 (15)0.0145 (17)0.0057 (15)
C20.0429 (18)0.049 (2)0.0401 (19)−0.0011 (16)0.0125 (16)0.0006 (16)
C30.059 (2)0.059 (3)0.045 (2)−0.004 (2)0.016 (2)0.0064 (19)
C40.051 (2)0.062 (3)0.059 (3)0.0028 (19)0.0181 (19)0.022 (2)
C50.0405 (19)0.0402 (19)0.063 (3)0.0012 (15)0.0062 (18)0.0205 (18)
C60.060 (2)0.0285 (16)0.0371 (18)0.0034 (15)0.0081 (16)0.0037 (14)
C70.065 (2)0.0340 (18)0.044 (2)−0.0035 (17)0.0238 (18)0.0093 (15)
C80.0305 (15)0.0190 (13)0.0514 (19)0.0003 (11)0.0117 (14)−0.0050 (13)
C90.0415 (16)0.0232 (14)0.057 (2)0.0065 (13)0.0248 (16)−0.0095 (14)
C100.056 (2)0.0351 (18)0.049 (2)0.0085 (16)0.0267 (18)0.0059 (15)
C110.056 (2)0.0302 (17)0.0373 (18)0.0018 (15)0.0051 (16)−0.0096 (14)
C120.0418 (18)0.0327 (17)0.0418 (19)−0.0009 (14)0.0127 (15)−0.0057 (14)
C130.0452 (18)0.0285 (15)0.0355 (16)−0.0006 (14)0.0131 (14)−0.0032 (13)
C140.0433 (17)0.0211 (13)0.0437 (18)−0.0080 (13)0.0219 (14)−0.0025 (13)
C150.059 (2)0.0371 (19)0.042 (2)−0.0016 (17)0.0098 (17)0.0057 (16)
C160.0444 (18)0.0261 (16)0.046 (2)0.0035 (14)−0.0019 (15)0.0028 (14)
C170.054 (2)0.0240 (15)0.0467 (19)−0.0027 (14)0.0147 (16)0.0017 (14)
C180.0411 (17)0.0337 (16)0.0341 (16)0.0100 (14)0.0159 (14)0.0021 (13)
C190.057 (2)0.0338 (17)0.0321 (16)0.0245 (15)0.0254 (15)0.0071 (13)
C200.0441 (18)0.0261 (15)0.049 (2)0.0134 (13)0.0197 (16)−0.0029 (14)
C210.0447 (18)0.0207 (13)0.0336 (17)0.0115 (12)0.0053 (14)0.0012 (12)
C220.046 (2)0.042 (2)0.059 (2)0.0082 (16)−0.0129 (18)0.0162 (18)
C230.052 (2)0.0274 (16)0.0436 (19)−0.0006 (14)−0.0014 (16)−0.0077 (14)
C240.0447 (19)0.0308 (16)0.050 (2)−0.0030 (14)0.0054 (16)0.0094 (15)
C250.059 (2)0.0331 (19)0.055 (2)0.0007 (16)−0.0121 (19)−0.0160 (16)
C260.050 (2)0.0294 (17)0.052 (2)0.0095 (14)−0.0156 (17)−0.0079 (15)
C270.060 (2)0.040 (2)0.043 (2)−0.0045 (16)0.0252 (18)0.0103 (16)
C280.0326 (15)0.0414 (18)0.0382 (17)−0.0001 (13)0.0152 (13)0.0158 (14)
C290.048 (2)0.047 (2)0.053 (2)0.0011 (17)0.0230 (18)0.0061 (17)
C300.045 (2)0.053 (2)0.039 (2)0.0013 (16)0.0026 (16)0.0023 (16)
C310.051 (2)0.044 (2)0.053 (2)0.0036 (17)0.0191 (18)0.0070 (17)
C320.052 (2)0.044 (2)0.057 (2)0.0019 (17)0.0231 (19)0.0163 (18)
C330.049 (2)0.053 (2)0.059 (3)0.0070 (18)0.020 (2)0.0074 (19)
C340.0322 (15)0.049 (2)0.0383 (18)−0.0087 (14)0.0087 (14)−0.0041 (15)
C350.057 (2)0.067 (3)0.038 (2)0.013 (2)0.0137 (17)0.0020 (18)
C360.0416 (19)0.047 (2)0.052 (2)−0.0066 (16)0.0224 (17)0.0010 (17)
C370.050 (2)0.050 (2)0.0422 (19)−0.0061 (16)0.0277 (16)0.0090 (16)
C380.054 (2)0.0417 (19)0.0286 (16)0.0002 (16)0.0112 (15)0.0004 (14)
C390.049 (2)0.042 (2)0.050 (2)0.0074 (16)0.0171 (17)0.0019 (16)
C400.046 (2)0.053 (2)0.050 (2)−0.0102 (17)0.0156 (18)−0.0104 (18)
C410.052 (2)0.053 (2)0.060 (3)−0.0086 (18)0.030 (2)−0.0151 (19)
C420.053 (2)0.046 (2)0.056 (2)0.0008 (17)0.0279 (18)−0.0146 (18)
C430.060 (2)0.0311 (18)0.055 (2)0.0016 (16)0.0264 (19)−0.0056 (16)
C440.0364 (17)0.047 (2)0.057 (2)−0.0018 (15)0.0211 (17)−0.0112 (17)
C450.056 (2)0.060 (2)0.0368 (19)−0.0081 (19)0.0127 (17)−0.0130 (17)
C460.060 (2)0.058 (2)0.0237 (16)−0.0101 (18)0.0073 (16)−0.0009 (15)
C470.0413 (18)0.053 (2)0.0330 (17)−0.0014 (15)0.0147 (14)−0.0052 (15)
C480.0393 (18)0.043 (2)0.058 (2)0.0094 (15)−0.0001 (17)0.0002 (18)
C490.048 (2)0.046 (2)0.056 (2)0.0143 (17)0.0266 (18)0.0156 (17)
C500.046 (2)0.044 (2)0.050 (2)−0.0041 (16)0.0168 (17)−0.0169 (17)
C510.049 (2)0.052 (2)0.052 (2)0.0156 (17)0.0310 (18)−0.0003 (17)
C520.069 (3)0.054 (2)0.0344 (19)−0.013 (2)0.0110 (18)−0.0182 (17)
N10.0447 (18)0.062 (2)0.051 (2)−0.0056 (16)0.0073 (15)0.0190 (18)
N20.0492 (18)0.0325 (16)0.061 (2)0.0058 (13)0.0167 (16)−0.0006 (14)
N30.060 (2)0.0323 (15)0.059 (2)0.0134 (14)0.0258 (17)0.0106 (14)
N40.0407 (16)0.059 (2)0.074 (2)−0.0129 (15)0.0368 (17)−0.0182 (18)
N50.060 (2)0.052 (2)0.065 (2)−0.0081 (17)0.0302 (18)0.0090 (18)
N60.0416 (16)0.055 (2)0.055 (2)0.0091 (14)0.0337 (15)0.0108 (16)
O10.0482 (15)0.0534 (17)0.0579 (18)0.0120 (13)0.0132 (13)0.0199 (14)
O20.0402 (14)0.0585 (17)0.0540 (16)−0.0084 (12)0.0203 (12)0.0111 (13)
O30.0461 (12)0.0225 (11)0.0516 (14)0.0126 (9)0.0185 (11)0.0055 (10)
O40.0571 (16)0.0349 (13)0.0460 (14)0.0099 (12)0.0175 (12)0.0055 (11)
O50.0531 (15)0.0542 (16)0.0460 (15)−0.0260 (12)0.0124 (12)−0.0079 (12)
O60.0542 (16)0.0463 (16)0.0557 (17)−0.0035 (12)0.0166 (13)−0.0040 (13)
O70.0435 (13)0.0539 (17)0.0458 (15)−0.0245 (12)0.0057 (11)0.0123 (12)
O80.0535 (16)0.0477 (15)0.0511 (16)−0.0099 (12)0.0208 (13)0.0168 (12)
Geometric parameters (Å, °) top
C1—N31.222 (5)C29—C301.397 (6)
C1—C61.411 (5)C29—H290.9300
C1—C21.426 (5)C30—C311.381 (5)
C2—C31.392 (5)C30—N41.424 (5)
C2—H20.9300C31—C321.367 (6)
C3—C41.429 (7)C31—H310.9300
C3—H30.9300C32—N51.435 (5)
C4—C51.352 (6)C33—N61.435 (6)
C4—N11.441 (5)C33—C341.562 (5)
C5—C61.383 (5)C33—H33A0.9700
C5—H50.9300C33—H33B0.9700
C6—N21.462 (5)C34—C481.510 (5)
C7—N31.544 (5)C34—C471.568 (5)
C7—C81.558 (5)C34—C351.584 (5)
C7—H7A0.9700C35—C361.474 (5)
C7—H7B0.9700C35—H35A0.9700
C8—C221.535 (5)C35—H35B0.9700
C8—C91.558 (5)C36—C371.569 (5)
C8—C211.587 (4)C36—H36A0.9700
C9—C101.486 (5)C36—H36B0.9700
C9—H9A0.9700C37—C381.568 (5)
C9—H9B0.9700C37—H37A0.9700
C10—C111.525 (5)C37—H37B0.9700
C10—H10A0.9700C38—C391.503 (6)
C10—H10B0.9700C38—C471.535 (5)
C11—C121.598 (5)C38—C491.554 (6)
C11—H11A0.9700C39—C441.421 (5)
C11—H11B0.9700C39—C401.423 (6)
C12—C231.508 (5)C40—C411.357 (6)
C12—C131.539 (5)C40—H400.9300
C12—C211.557 (5)C41—C421.413 (5)
C13—C141.342 (5)C41—H410.9300
C13—C181.400 (4)C42—C431.343 (5)
C14—C151.424 (5)C42—C501.570 (6)
C14—H140.9300C43—C441.395 (5)
C15—C161.405 (5)C43—H430.9300
C15—H150.9300C44—C451.506 (5)
C16—C171.412 (5)C45—C461.500 (6)
C16—C241.506 (5)C45—H45A0.9700
C17—C181.399 (5)C45—H45B0.9700
C17—H170.9300C46—C471.551 (5)
C18—C191.558 (4)C46—H46A0.9700
C19—C201.521 (4)C46—H46B0.9700
C19—H19A0.9700C47—H470.9800
C19—H19B0.9700C48—H48A0.9600
C20—C211.550 (4)C48—H48B0.9600
C20—H20A0.9700C48—H48C0.9600
C20—H20B0.9700C49—H49A0.9600
C21—H210.9800C49—H49B0.9600
C22—H22A0.9600C49—H49C0.9600
C22—H22B0.9600C50—C511.511 (6)
C22—H22C0.9600C50—C521.512 (5)
C23—H23A0.9600C50—H500.9800
C23—H23B0.9600C51—H51A0.9600
C23—H23C0.9600C51—H51B0.9600
C24—C261.507 (5)C51—H51C0.9600
C24—C251.542 (5)C52—H52A0.9600
C24—H240.9800C52—H52B0.9600
C25—H25A0.9600C52—H52C0.9600
C25—H25B0.9600N1—O11.217 (5)
C25—H25C0.9600N1—O21.226 (5)
C26—H26A0.9600N2—O41.204 (4)
C26—H26B0.9600N2—O31.237 (4)
C26—H26C0.9600N3—H3A0.86 (5)
C27—N61.326 (5)N4—O61.206 (4)
C27—C281.404 (4)N4—O51.247 (4)
C27—C321.461 (6)N5—O71.200 (5)
C28—C291.403 (5)N5—O81.273 (5)
C28—H280.9300N6—H60.86 (5)
N3—C1—C6124.4 (4)C31—C30—C29122.4 (4)
N3—C1—C2121.9 (4)C31—C30—N4118.8 (4)
C6—C1—C2113.5 (3)C29—C30—N4118.8 (4)
C3—C2—C1125.3 (4)C32—C31—C30119.5 (4)
C3—C2—H2117.4C32—C31—H31120.3
C1—C2—H2117.4C30—C31—H31120.3
C2—C3—C4114.9 (4)C31—C32—N5116.3 (4)
C2—C3—H3122.6C31—C32—C27121.3 (3)
C4—C3—H3122.6N5—C32—C27122.3 (4)
C5—C4—C3123.4 (4)N6—C33—C34110.6 (3)
C5—C4—N1120.5 (4)N6—C33—H33A109.5
C3—C4—N1116.1 (4)C34—C33—H33A109.5
C4—C5—C6118.6 (4)N6—C33—H33B109.5
C4—C5—H5120.7C34—C33—H33B109.5
C6—C5—H5120.7H33A—C33—H33B108.1
C5—C6—C1124.1 (4)C48—C34—C33110.8 (3)
C5—C6—N2114.6 (3)C48—C34—C47113.9 (3)
C1—C6—N2121.2 (3)C33—C34—C47106.8 (3)
N3—C7—C8112.3 (3)C48—C34—C35112.5 (3)
N3—C7—H7A109.1C33—C34—C35106.2 (3)
C8—C7—H7A109.1C47—C34—C35106.2 (3)
N3—C7—H7B109.1C36—C35—C34114.0 (3)
C8—C7—H7B109.1C36—C35—H35A108.8
H7A—C7—H7B107.9C34—C35—H35A108.8
C22—C8—C9113.6 (3)C36—C35—H35B108.8
C22—C8—C7107.1 (3)C34—C35—H35B108.8
C9—C8—C7112.4 (3)H35A—C35—H35B107.6
C22—C8—C21114.6 (3)C35—C36—C37111.8 (3)
C9—C8—C21105.8 (3)C35—C36—H36A109.3
C7—C8—C21102.9 (3)C37—C36—H36A109.3
C10—C9—C8115.7 (3)C35—C36—H36B109.3
C10—C9—H9A108.3C37—C36—H36B109.3
C8—C9—H9A108.3H36A—C36—H36B107.9
C10—C9—H9B108.3C38—C37—C36111.0 (3)
C8—C9—H9B108.3C38—C37—H37A109.4
H9A—C9—H9B107.4C36—C37—H37A109.4
C9—C10—C11109.3 (3)C38—C37—H37B109.4
C9—C10—H10A109.8C36—C37—H37B109.4
C11—C10—H10A109.8H37A—C37—H37B108.0
C9—C10—H10B109.8C39—C38—C47109.5 (3)
C11—C10—H10B109.8C39—C38—C49106.3 (3)
H10A—C10—H10B108.3C47—C38—C49113.3 (3)
C10—C11—C12111.4 (3)C39—C38—C37108.6 (3)
C10—C11—H11A109.3C47—C38—C37109.3 (3)
C12—C11—H11A109.3C49—C38—C37109.7 (3)
C10—C11—H11B109.3C44—C39—C40115.7 (4)
C12—C11—H11B109.3C44—C39—C38120.9 (3)
H11A—C11—H11B108.0C40—C39—C38123.3 (3)
C23—C12—C13106.8 (3)C41—C40—C39124.4 (4)
C23—C12—C21118.2 (3)C41—C40—H40117.8
C13—C12—C21109.3 (3)C39—C40—H40117.8
C23—C12—C11108.7 (3)C40—C41—C42117.1 (4)
C13—C12—C11106.7 (3)C40—C41—H41121.5
C21—C12—C11106.5 (3)C42—C41—H41121.5
C14—C13—C18117.5 (3)C43—C42—C41120.4 (4)
C14—C13—C12122.1 (3)C43—C42—C50122.5 (3)
C18—C13—C12120.3 (3)C41—C42—C50116.8 (3)
C13—C14—C15123.5 (3)C42—C43—C44122.4 (4)
C13—C14—H14118.3C42—C43—H43118.8
C15—C14—H14118.3C44—C43—H43118.8
C16—C15—C14119.5 (3)C43—C44—C39119.1 (3)
C16—C15—H15120.2C43—C44—C45119.5 (3)
C14—C15—H15120.2C39—C44—C45121.4 (4)
C15—C16—C17116.9 (3)C46—C45—C44114.3 (3)
C15—C16—C24122.6 (3)C46—C45—H45A108.7
C17—C16—C24120.4 (3)C44—C45—H45A108.7
C18—C17—C16121.2 (3)C46—C45—H45B108.7
C18—C17—H17119.4C44—C45—H45B108.7
C16—C17—H17119.4H45A—C45—H45B107.6
C17—C18—C13121.3 (3)C45—C46—C47110.1 (3)
C17—C18—C19115.1 (3)C45—C46—H46A109.6
C13—C18—C19123.6 (3)C47—C46—H46A109.6
C20—C19—C18110.9 (3)C45—C46—H46B109.6
C20—C19—H19A109.5C47—C46—H46B109.6
C18—C19—H19A109.5H46A—C46—H46B108.2
C20—C19—H19B109.5C38—C47—C46107.7 (3)
C18—C19—H19B109.5C38—C47—C34118.8 (3)
H19A—C19—H19B108.1C46—C47—C34114.1 (3)
C19—C20—C21108.5 (3)C38—C47—H47105.0
C19—C20—H20A110.0C46—C47—H47105.0
C21—C20—H20A110.0C34—C47—H47105.0
C19—C20—H20B110.0C34—C48—H48A109.5
C21—C20—H20B110.0C34—C48—H48B109.5
H20A—C20—H20B108.4H48A—C48—H48B109.5
C20—C21—C12107.7 (3)C34—C48—H48C109.5
C20—C21—C8116.1 (3)H48A—C48—H48C109.5
C12—C21—C8114.7 (3)H48B—C48—H48C109.5
C20—C21—H21105.8C38—C49—H49A109.5
C12—C21—H21105.8C38—C49—H49B109.5
C8—C21—H21105.8H49A—C49—H49B109.5
C8—C22—H22A109.5C38—C49—H49C109.5
C8—C22—H22B109.5H49A—C49—H49C109.5
H22A—C22—H22B109.5H49B—C49—H49C109.5
C8—C22—H22C109.5C51—C50—C52105.8 (3)
H22A—C22—H22C109.5C51—C50—C42107.0 (3)
H22B—C22—H22C109.5C52—C50—C42117.7 (3)
C12—C23—H23A109.5C51—C50—H50108.7
C12—C23—H23B109.5C52—C50—H50108.7
H23A—C23—H23B109.5C42—C50—H50108.7
C12—C23—H23C109.5C50—C51—H51A109.5
H23A—C23—H23C109.5C50—C51—H51B109.5
H23B—C23—H23C109.5H51A—C51—H51B109.5
C16—C24—C26113.2 (3)C50—C51—H51C109.5
C16—C24—C25108.8 (3)H51A—C51—H51C109.5
C26—C24—C25108.3 (3)H51B—C51—H51C109.5
C16—C24—H24108.9C50—C52—H52A109.5
C26—C24—H24108.9C50—C52—H52B109.5
C25—C24—H24108.9H52A—C52—H52B109.5
C24—C25—H25A109.5C50—C52—H52C109.5
C24—C25—H25B109.5H52A—C52—H52C109.5
H25A—C25—H25B109.5H52B—C52—H52C109.5
C24—C25—H25C109.5O1—N1—O2122.1 (3)
H25A—C25—H25C109.5O1—N1—C4120.1 (4)
H25B—C25—H25C109.5O2—N1—C4117.8 (4)
C24—C26—H26A109.5O4—N2—O3121.2 (3)
C24—C26—H26B109.5O4—N2—C6120.9 (3)
H26A—C26—H26B109.5O3—N2—C6117.4 (3)
C24—C26—H26C109.5C1—N3—C7130.3 (3)
H26A—C26—H26C109.5C1—N3—H3A115 (3)
H26B—C26—H26C109.5C7—N3—H3A115 (3)
N6—C27—C28121.2 (3)O6—N4—O5118.7 (3)
N6—C27—C32122.2 (3)O6—N4—C30121.2 (3)
C28—C27—C32116.5 (3)O5—N4—C30120.0 (4)
C29—C28—C27121.9 (3)O7—N5—O8122.5 (3)
C29—C28—H28119.1O7—N5—C32120.0 (4)
C27—C28—H28119.1O8—N5—C32117.2 (3)
C30—C29—C28118.1 (3)C27—N6—C33125.6 (3)
C30—C29—H29120.9C27—N6—H6117 (3)
C28—C29—H29120.9C33—N6—H6117 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O40.86 (5)1.95 (5)2.650 (4)137 (4)
N6—H6···O80.86 (5)1.99 (5)2.643 (4)132 (4)
C10—H10A···O5i0.972.243.078 (5)144
C23—H23B···O5i0.962.463.242 (5)139
C41—H41···O8ii0.932.553.435 (5)159
Symmetry codes: (i) −x+1, y+1/2, −z+2; (ii) −x+2, y−1/2, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O40.86 (5)1.95 (5)2.650 (4)137 (4)
N6—H6···O80.86 (5)1.99 (5)2.643 (4)132 (4)
C10—H10A···O5i0.972.243.078 (5)144
C23—H23B···O5i0.962.463.242 (5)139
C41—H41···O8ii0.932.553.435 (5)159
Symmetry codes: (i) −x+1, y+1/2, −z+2; (ii) −x+2, y−1/2, −z.
Acknowledgements top

We acknowledge the National Natural Science Foundation of China (No. 20604011) and the Six-Profession Talents Summit Program of Jiangsu Province (No. 06-A-018) for support of this research.

references
References top

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