organic compounds
N-(2,4-Dinitrophenyl)dehydroabietylamine
aSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People's Republic of China, bDepartment of Polymer Science and Engineering, School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, People's Republic of China, and cMedical School, Nanjing University, Nanjing 210093, People's Republic of China
*Correspondence e-mail: huanglq@nju.edu.cn
In the 26H33N3O4, 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.
of the title compound, CRelated literature
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
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808010490/is2284sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010490/is2284Isup2.hkl
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
(n-hexane/ethyl acetate as eluent) and then recrystallized from methanol to give the title compound (yield 35.5%, m.p. 408–409 K).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
effects, Friedel pairs have been merged.Data collection: SMART (Bruker, 2000); cell
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).C26H33N3O4 | F(000) = 968 |
Mr = 451.55 | Dx = 1.249 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1357 reflections |
a = 14.119 (7) Å | θ = 2.9–18.1° |
b = 23.574 (12) Å | µ = 0.09 mm−1 |
c = 7.309 (4) Å | T = 291 K |
β = 99.191 (9)° | Block, light-yellow |
V = 2402 (2) Å3 | 0.30 × 0.26 × 0.24 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 6027 independent reflections |
Radiation source: sealed tube | 4715 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
ϕ and ω scans | θmax = 28.6°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −16→18 |
Tmin = 0.98, Tmax = 0.98 | k = −31→31 |
15350 measured reflections | l = −9→9 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.07P)2] where P = (Fo2 + 2Fc2)/3 |
6027 reflections | (Δ/σ)max < 0.001 |
609 parameters | Δρmax = 0.19 e Å−3 |
1 restraint | Δρmin = −0.19 e Å−3 |
C26H33N3O4 | V = 2402 (2) Å3 |
Mr = 451.55 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 14.119 (7) Å | µ = 0.09 mm−1 |
b = 23.574 (12) Å | T = 291 K |
c = 7.309 (4) Å | 0.30 × 0.26 × 0.24 mm |
β = 99.191 (9)° |
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 = 0.98 | Rint = 0.046 |
15350 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 1 restraint |
wR(F2) = 0.139 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.19 e Å−3 |
6027 reflections | Δρmin = −0.19 e Å−3 |
609 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6051 (3) | 1.03496 (15) | 0.3284 (6) | 0.0432 (8) | |
C2 | 0.6497 (3) | 1.01296 (18) | 0.1815 (5) | 0.0433 (8) | |
H2 | 0.6574 | 0.9738 | 0.1763 | 0.052* | |
C3 | 0.6826 (3) | 1.0453 (2) | 0.0451 (6) | 0.0539 (10) | |
H3 | 0.7101 | 1.0292 | −0.0501 | 0.065* | |
C4 | 0.6711 (3) | 1.1052 (2) | 0.0627 (7) | 0.0562 (11) | |
C5 | 0.6347 (3) | 1.12950 (17) | 0.2041 (6) | 0.0481 (9) | |
H5 | 0.6308 | 1.1688 | 0.2131 | 0.058* | |
C6 | 0.6036 (3) | 1.09476 (15) | 0.3349 (5) | 0.0419 (8) | |
C7 | 0.5823 (3) | 0.93895 (15) | 0.4645 (6) | 0.0462 (9) | |
H7A | 0.6455 | 0.9286 | 0.5285 | 0.055* | |
H7B | 0.5737 | 0.9215 | 0.3428 | 0.055* | |
C8 | 0.5050 (2) | 0.91540 (12) | 0.5747 (5) | 0.0331 (7) | |
C9 | 0.5037 (3) | 0.94785 (13) | 0.7600 (5) | 0.0386 (8) | |
H9A | 0.5694 | 0.9527 | 0.8211 | 0.046* | |
H9B | 0.4773 | 0.9854 | 0.7309 | 0.046* | |
C10 | 0.4483 (3) | 0.92050 (15) | 0.8925 (6) | 0.0447 (9) | |
H10A | 0.3817 | 0.9166 | 0.8359 | 0.054* | |
H10B | 0.4509 | 0.9439 | 1.0024 | 0.054* | |
C11 | 0.4910 (3) | 0.86223 (14) | 0.9458 (5) | 0.0415 (8) | |
H11A | 0.4554 | 0.8445 | 1.0336 | 0.050* | |
H11B | 0.5570 | 0.8666 | 1.0057 | 0.050* | |
C12 | 0.4876 (3) | 0.82217 (15) | 0.7685 (5) | 0.0381 (7) | |
C13 | 0.5412 (3) | 0.76731 (14) | 0.8357 (5) | 0.0357 (7) | |
C14 | 0.5280 (2) | 0.74107 (13) | 0.9926 (5) | 0.0344 (7) | |
H14 | 0.4851 | 0.7570 | 1.0623 | 0.041* | |
C15 | 0.5761 (3) | 0.69012 (16) | 1.0579 (5) | 0.0459 (8) | |
H15 | 0.5650 | 0.6737 | 1.1683 | 0.055* | |
C16 | 0.6404 (3) | 0.66476 (14) | 0.9544 (5) | 0.0398 (8) | |
C17 | 0.6516 (3) | 0.69130 (14) | 0.7860 (5) | 0.0407 (8) | |
H17 | 0.6923 | 0.6752 | 0.7122 | 0.049* | |
C18 | 0.6025 (2) | 0.74134 (14) | 0.7281 (5) | 0.0352 (7) | |
C19 | 0.6249 (3) | 0.76646 (14) | 0.5425 (5) | 0.0390 (8) | |
H19A | 0.6892 | 0.7822 | 0.5620 | 0.047* | |
H19B | 0.6224 | 0.7365 | 0.4510 | 0.047* | |
C20 | 0.5532 (3) | 0.81258 (14) | 0.4705 (5) | 0.0383 (8) | |
H20A | 0.4914 | 0.7958 | 0.4236 | 0.046* | |
H20B | 0.5752 | 0.8331 | 0.3701 | 0.046* | |
C21 | 0.5437 (3) | 0.85369 (13) | 0.6321 (5) | 0.0331 (7) | |
H21 | 0.6089 | 0.8590 | 0.6994 | 0.040* | |
C22 | 0.4086 (3) | 0.91669 (18) | 0.4435 (6) | 0.0513 (10) | |
H22A | 0.3573 | 0.9200 | 0.5147 | 0.077* | |
H22B | 0.4010 | 0.8823 | 0.3723 | 0.077* | |
H22C | 0.4072 | 0.9486 | 0.3615 | 0.077* | |
C23 | 0.3848 (3) | 0.80579 (14) | 0.7005 (5) | 0.0421 (8) | |
H23A | 0.3797 | 0.7896 | 0.5788 | 0.063* | |
H23B | 0.3448 | 0.8389 | 0.6957 | 0.063* | |
H23C | 0.3644 | 0.7785 | 0.7836 | 0.063* | |
C24 | 0.6938 (3) | 0.61086 (15) | 1.0142 (6) | 0.0420 (8) | |
H24 | 0.7451 | 0.6057 | 0.9399 | 0.050* | |
C25 | 0.6235 (3) | 0.56052 (16) | 0.9783 (6) | 0.0513 (10) | |
H25A | 0.6583 | 0.5268 | 0.9571 | 0.077* | |
H25B | 0.5764 | 0.5684 | 0.8713 | 0.077* | |
H25C | 0.5921 | 0.5551 | 1.0842 | 0.077* | |
C26 | 0.7371 (3) | 0.61064 (15) | 1.2165 (6) | 0.0462 (9) | |
H26A | 0.6879 | 0.6031 | 1.2901 | 0.069* | |
H26B | 0.7655 | 0.6470 | 1.2499 | 0.069* | |
H26C | 0.7854 | 0.5817 | 1.2386 | 0.069* | |
C27 | 0.8660 (3) | 0.30147 (16) | 0.5585 (5) | 0.0461 (9) | |
C28 | 0.8144 (2) | 0.28052 (15) | 0.6931 (5) | 0.0364 (7) | |
H28 | 0.7932 | 0.2431 | 0.6848 | 0.044* | |
C29 | 0.7940 (3) | 0.31439 (17) | 0.8397 (6) | 0.0476 (9) | |
H29 | 0.7646 | 0.2991 | 0.9338 | 0.057* | |
C30 | 0.8189 (3) | 0.37176 (18) | 0.8405 (5) | 0.0461 (9) | |
C31 | 0.8630 (3) | 0.39573 (17) | 0.7035 (6) | 0.0481 (9) | |
H31 | 0.8753 | 0.4345 | 0.7041 | 0.058* | |
C32 | 0.8884 (3) | 0.36200 (17) | 0.5670 (6) | 0.0496 (10) | |
C33 | 0.8782 (3) | 0.20752 (18) | 0.4190 (7) | 0.0526 (10) | |
H33A | 0.8187 | 0.1987 | 0.3378 | 0.063* | |
H33B | 0.8737 | 0.1928 | 0.5413 | 0.063* | |
C34 | 0.9638 (2) | 0.17850 (16) | 0.3441 (5) | 0.0394 (8) | |
C35 | 0.9616 (3) | 0.2017 (2) | 0.1400 (6) | 0.0533 (10) | |
H35A | 0.8959 | 0.2009 | 0.0759 | 0.064* | |
H35B | 0.9825 | 0.2409 | 0.1467 | 0.064* | |
C36 | 1.0223 (3) | 0.16940 (16) | 0.0306 (6) | 0.0451 (9) | |
H36A | 1.0886 | 0.1716 | 0.0908 | 0.054* | |
H36B | 1.0181 | 0.1864 | −0.0913 | 0.054* | |
C37 | 0.9912 (3) | 0.10552 (17) | 0.0095 (6) | 0.0451 (9) | |
H37A | 0.9266 | 0.1031 | −0.0593 | 0.054* | |
H37B | 1.0338 | 0.0855 | −0.0601 | 0.054* | |
C38 | 0.9944 (3) | 0.07674 (16) | 0.2038 (5) | 0.0410 (8) | |
C39 | 0.9476 (3) | 0.01943 (17) | 0.1764 (6) | 0.0462 (9) | |
C40 | 0.9525 (3) | −0.01538 (18) | 0.0191 (6) | 0.0487 (9) | |
H40 | 0.9807 | −0.0001 | −0.0765 | 0.058* | |
C41 | 0.9189 (3) | −0.06933 (18) | −0.0008 (6) | 0.0527 (10) | |
H41 | 0.9299 | −0.0920 | −0.0995 | 0.063* | |
C42 | 0.8665 (3) | −0.08959 (17) | 0.1350 (6) | 0.0495 (9) | |
C43 | 0.8643 (3) | −0.05987 (15) | 0.2910 (6) | 0.0469 (9) | |
H43 | 0.8387 | −0.0768 | 0.3871 | 0.056* | |
C44 | 0.8990 (3) | −0.00449 (16) | 0.3140 (6) | 0.0454 (9) | |
C45 | 0.8833 (3) | 0.02884 (19) | 0.4823 (5) | 0.0504 (9) | |
H45A | 0.8157 | 0.0382 | 0.4710 | 0.060* | |
H45B | 0.8995 | 0.0050 | 0.5910 | 0.060* | |
C46 | 0.9406 (3) | 0.08257 (18) | 0.5118 (5) | 0.0472 (9) | |
H46A | 1.0063 | 0.0738 | 0.5659 | 0.057* | |
H46B | 0.9137 | 0.1070 | 0.5971 | 0.057* | |
C47 | 0.9395 (3) | 0.11368 (17) | 0.3245 (5) | 0.0414 (8) | |
H47 | 0.8725 | 0.1122 | 0.2635 | 0.050* | |
C48 | 1.0574 (3) | 0.19114 (17) | 0.4684 (6) | 0.0478 (9) | |
H48A | 1.0632 | 0.2313 | 0.4892 | 0.072* | |
H48B | 1.1098 | 0.1781 | 0.4102 | 0.072* | |
H48C | 1.0589 | 0.1720 | 0.5847 | 0.072* | |
C49 | 1.1003 (3) | 0.06585 (17) | 0.2926 (6) | 0.0477 (9) | |
H49A | 1.1022 | 0.0490 | 0.4127 | 0.071* | |
H49B | 1.1346 | 0.1012 | 0.3049 | 0.071* | |
H49C | 1.1297 | 0.0407 | 0.2150 | 0.071* | |
C50 | 0.8210 (3) | −0.15026 (17) | 0.1030 (6) | 0.0457 (9) | |
H50 | 0.7520 | −0.1475 | 0.1065 | 0.055* | |
C51 | 0.8665 (3) | −0.18691 (18) | 0.2626 (6) | 0.0485 (9) | |
H51A | 0.8173 | −0.2052 | 0.3177 | 0.073* | |
H51B | 0.9050 | −0.1637 | 0.3537 | 0.073* | |
H51C | 0.9063 | −0.2151 | 0.2180 | 0.073* | |
C52 | 0.8352 (3) | −0.18168 (19) | −0.0710 (5) | 0.0524 (10) | |
H52A | 0.8988 | −0.1972 | −0.0552 | 0.079* | |
H52B | 0.8266 | −0.1559 | −0.1740 | 0.079* | |
H52C | 0.7891 | −0.2118 | −0.0941 | 0.079* | |
N1 | 0.7052 (2) | 1.13979 (16) | −0.0758 (5) | 0.0526 (9) | |
N2 | 0.5607 (2) | 1.12477 (13) | 0.4765 (5) | 0.0467 (8) | |
N3 | 0.5767 (3) | 1.00406 (13) | 0.4424 (5) | 0.0487 (8) | |
H3A | 0.549 (3) | 1.021 (2) | 0.523 (7) | 0.058* | |
N4 | 0.7997 (2) | 0.40656 (16) | 0.9895 (6) | 0.0549 (9) | |
N5 | 0.9317 (3) | 0.39006 (16) | 0.4270 (6) | 0.0568 (9) | |
N6 | 0.8912 (2) | 0.26788 (15) | 0.4290 (5) | 0.0478 (8) | |
H6 | 0.918 (3) | 0.284 (2) | 0.344 (7) | 0.057* | |
O1 | 0.7368 (2) | 1.11758 (13) | −0.2038 (4) | 0.0527 (7) | |
O2 | 0.70301 (19) | 1.19145 (13) | −0.0571 (4) | 0.0495 (7) | |
O3 | 0.57835 (17) | 1.17599 (9) | 0.4971 (4) | 0.0389 (5) | |
O4 | 0.5187 (2) | 1.09936 (10) | 0.5818 (4) | 0.0450 (6) | |
O5 | 0.7625 (2) | 0.38555 (12) | 1.1176 (4) | 0.0506 (7) | |
O6 | 0.8212 (2) | 0.45609 (12) | 0.9977 (4) | 0.0512 (7) | |
O7 | 0.93068 (18) | 0.44089 (12) | 0.4172 (4) | 0.0479 (6) | |
O8 | 0.9785 (2) | 0.35937 (12) | 0.3293 (4) | 0.0494 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.055 (2) | 0.0282 (17) | 0.048 (2) | −0.0011 (15) | 0.0145 (17) | 0.0057 (15) |
C2 | 0.0429 (18) | 0.049 (2) | 0.0401 (19) | −0.0011 (16) | 0.0125 (16) | 0.0006 (16) |
C3 | 0.059 (2) | 0.059 (3) | 0.045 (2) | −0.004 (2) | 0.016 (2) | 0.0064 (19) |
C4 | 0.051 (2) | 0.062 (3) | 0.059 (3) | 0.0028 (19) | 0.0181 (19) | 0.022 (2) |
C5 | 0.0405 (19) | 0.0402 (19) | 0.063 (3) | 0.0012 (15) | 0.0062 (18) | 0.0205 (18) |
C6 | 0.060 (2) | 0.0285 (16) | 0.0371 (18) | 0.0034 (15) | 0.0081 (16) | 0.0037 (14) |
C7 | 0.065 (2) | 0.0340 (18) | 0.044 (2) | −0.0035 (17) | 0.0238 (18) | 0.0093 (15) |
C8 | 0.0305 (15) | 0.0190 (13) | 0.0514 (19) | 0.0003 (11) | 0.0117 (14) | −0.0050 (13) |
C9 | 0.0415 (16) | 0.0232 (14) | 0.057 (2) | 0.0065 (13) | 0.0248 (16) | −0.0095 (14) |
C10 | 0.056 (2) | 0.0351 (18) | 0.049 (2) | 0.0085 (16) | 0.0267 (18) | 0.0059 (15) |
C11 | 0.056 (2) | 0.0302 (17) | 0.0373 (18) | 0.0018 (15) | 0.0051 (16) | −0.0096 (14) |
C12 | 0.0418 (18) | 0.0327 (17) | 0.0418 (19) | −0.0009 (14) | 0.0127 (15) | −0.0057 (14) |
C13 | 0.0452 (18) | 0.0285 (15) | 0.0355 (16) | −0.0006 (14) | 0.0131 (14) | −0.0032 (13) |
C14 | 0.0433 (17) | 0.0211 (13) | 0.0437 (18) | −0.0080 (13) | 0.0219 (14) | −0.0025 (13) |
C15 | 0.059 (2) | 0.0371 (19) | 0.042 (2) | −0.0016 (17) | 0.0098 (17) | 0.0057 (16) |
C16 | 0.0444 (18) | 0.0261 (16) | 0.046 (2) | 0.0035 (14) | −0.0019 (15) | 0.0028 (14) |
C17 | 0.054 (2) | 0.0240 (15) | 0.0467 (19) | −0.0027 (14) | 0.0147 (16) | 0.0017 (14) |
C18 | 0.0411 (17) | 0.0337 (16) | 0.0341 (16) | 0.0100 (14) | 0.0159 (14) | 0.0021 (13) |
C19 | 0.057 (2) | 0.0338 (17) | 0.0321 (16) | 0.0245 (15) | 0.0254 (15) | 0.0071 (13) |
C20 | 0.0441 (18) | 0.0261 (15) | 0.049 (2) | 0.0134 (13) | 0.0197 (16) | −0.0029 (14) |
C21 | 0.0447 (18) | 0.0207 (13) | 0.0336 (17) | 0.0115 (12) | 0.0053 (14) | 0.0012 (12) |
C22 | 0.046 (2) | 0.042 (2) | 0.059 (2) | 0.0082 (16) | −0.0129 (18) | 0.0162 (18) |
C23 | 0.052 (2) | 0.0274 (16) | 0.0436 (19) | −0.0006 (14) | −0.0014 (16) | −0.0077 (14) |
C24 | 0.0447 (19) | 0.0308 (16) | 0.050 (2) | −0.0030 (14) | 0.0054 (16) | 0.0094 (15) |
C25 | 0.059 (2) | 0.0331 (19) | 0.055 (2) | 0.0007 (16) | −0.0121 (19) | −0.0160 (16) |
C26 | 0.050 (2) | 0.0294 (17) | 0.052 (2) | 0.0095 (14) | −0.0156 (17) | −0.0079 (15) |
C27 | 0.060 (2) | 0.040 (2) | 0.043 (2) | −0.0045 (16) | 0.0252 (18) | 0.0103 (16) |
C28 | 0.0326 (15) | 0.0414 (18) | 0.0382 (17) | −0.0001 (13) | 0.0152 (13) | 0.0158 (14) |
C29 | 0.048 (2) | 0.047 (2) | 0.053 (2) | 0.0011 (17) | 0.0230 (18) | 0.0061 (17) |
C30 | 0.045 (2) | 0.053 (2) | 0.039 (2) | 0.0013 (16) | 0.0026 (16) | 0.0023 (16) |
C31 | 0.051 (2) | 0.044 (2) | 0.053 (2) | 0.0036 (17) | 0.0191 (18) | 0.0070 (17) |
C32 | 0.052 (2) | 0.044 (2) | 0.057 (2) | 0.0019 (17) | 0.0231 (19) | 0.0163 (18) |
C33 | 0.049 (2) | 0.053 (2) | 0.059 (3) | 0.0070 (18) | 0.020 (2) | 0.0074 (19) |
C34 | 0.0322 (15) | 0.049 (2) | 0.0383 (18) | −0.0087 (14) | 0.0087 (14) | −0.0041 (15) |
C35 | 0.057 (2) | 0.067 (3) | 0.038 (2) | 0.013 (2) | 0.0137 (17) | 0.0020 (18) |
C36 | 0.0416 (19) | 0.047 (2) | 0.052 (2) | −0.0066 (16) | 0.0224 (17) | 0.0010 (17) |
C37 | 0.050 (2) | 0.050 (2) | 0.0422 (19) | −0.0061 (16) | 0.0277 (16) | 0.0090 (16) |
C38 | 0.054 (2) | 0.0417 (19) | 0.0286 (16) | 0.0002 (16) | 0.0112 (15) | 0.0004 (14) |
C39 | 0.049 (2) | 0.042 (2) | 0.050 (2) | 0.0074 (16) | 0.0171 (17) | 0.0019 (16) |
C40 | 0.046 (2) | 0.053 (2) | 0.050 (2) | −0.0102 (17) | 0.0156 (18) | −0.0104 (18) |
C41 | 0.052 (2) | 0.053 (2) | 0.060 (3) | −0.0086 (18) | 0.030 (2) | −0.0151 (19) |
C42 | 0.053 (2) | 0.046 (2) | 0.056 (2) | 0.0008 (17) | 0.0279 (18) | −0.0146 (18) |
C43 | 0.060 (2) | 0.0311 (18) | 0.055 (2) | 0.0016 (16) | 0.0264 (19) | −0.0056 (16) |
C44 | 0.0364 (17) | 0.047 (2) | 0.057 (2) | −0.0018 (15) | 0.0211 (17) | −0.0112 (17) |
C45 | 0.056 (2) | 0.060 (2) | 0.0368 (19) | −0.0081 (19) | 0.0127 (17) | −0.0130 (17) |
C46 | 0.060 (2) | 0.058 (2) | 0.0237 (16) | −0.0101 (18) | 0.0073 (16) | −0.0009 (15) |
C47 | 0.0413 (18) | 0.053 (2) | 0.0330 (17) | −0.0014 (15) | 0.0147 (14) | −0.0052 (15) |
C48 | 0.0393 (18) | 0.043 (2) | 0.058 (2) | 0.0094 (15) | −0.0001 (17) | 0.0002 (18) |
C49 | 0.048 (2) | 0.046 (2) | 0.056 (2) | 0.0143 (17) | 0.0266 (18) | 0.0156 (17) |
C50 | 0.046 (2) | 0.044 (2) | 0.050 (2) | −0.0041 (16) | 0.0168 (17) | −0.0169 (17) |
C51 | 0.049 (2) | 0.052 (2) | 0.052 (2) | 0.0156 (17) | 0.0310 (18) | −0.0003 (17) |
C52 | 0.069 (3) | 0.054 (2) | 0.0344 (19) | −0.013 (2) | 0.0110 (18) | −0.0182 (17) |
N1 | 0.0447 (18) | 0.062 (2) | 0.051 (2) | −0.0056 (16) | 0.0073 (15) | 0.0190 (18) |
N2 | 0.0492 (18) | 0.0325 (16) | 0.061 (2) | 0.0058 (13) | 0.0167 (16) | −0.0006 (14) |
N3 | 0.060 (2) | 0.0323 (15) | 0.059 (2) | 0.0134 (14) | 0.0258 (17) | 0.0106 (14) |
N4 | 0.0407 (16) | 0.059 (2) | 0.074 (2) | −0.0129 (15) | 0.0368 (17) | −0.0182 (18) |
N5 | 0.060 (2) | 0.052 (2) | 0.065 (2) | −0.0081 (17) | 0.0302 (18) | 0.0090 (18) |
N6 | 0.0416 (16) | 0.055 (2) | 0.055 (2) | 0.0091 (14) | 0.0337 (15) | 0.0108 (16) |
O1 | 0.0482 (15) | 0.0534 (17) | 0.0579 (18) | 0.0120 (13) | 0.0132 (13) | 0.0199 (14) |
O2 | 0.0402 (14) | 0.0585 (17) | 0.0540 (16) | −0.0084 (12) | 0.0203 (12) | 0.0111 (13) |
O3 | 0.0461 (12) | 0.0225 (11) | 0.0516 (14) | 0.0126 (9) | 0.0185 (11) | 0.0055 (10) |
O4 | 0.0571 (16) | 0.0349 (13) | 0.0460 (14) | 0.0099 (12) | 0.0175 (12) | 0.0055 (11) |
O5 | 0.0531 (15) | 0.0542 (16) | 0.0460 (15) | −0.0260 (12) | 0.0124 (12) | −0.0079 (12) |
O6 | 0.0542 (16) | 0.0463 (16) | 0.0557 (17) | −0.0035 (12) | 0.0166 (13) | −0.0040 (13) |
O7 | 0.0435 (13) | 0.0539 (17) | 0.0458 (15) | −0.0245 (12) | 0.0057 (11) | 0.0123 (12) |
O8 | 0.0535 (16) | 0.0477 (15) | 0.0511 (16) | −0.0099 (12) | 0.0208 (13) | 0.0168 (12) |
C1—N3 | 1.222 (5) | C29—C30 | 1.397 (6) |
C1—C6 | 1.411 (5) | C29—H29 | 0.9300 |
C1—C2 | 1.426 (5) | C30—C31 | 1.381 (5) |
C2—C3 | 1.392 (5) | C30—N4 | 1.424 (5) |
C2—H2 | 0.9300 | C31—C32 | 1.367 (6) |
C3—C4 | 1.429 (7) | C31—H31 | 0.9300 |
C3—H3 | 0.9300 | C32—N5 | 1.435 (5) |
C4—C5 | 1.352 (6) | C33—N6 | 1.435 (6) |
C4—N1 | 1.441 (5) | C33—C34 | 1.562 (5) |
C5—C6 | 1.383 (5) | C33—H33A | 0.9700 |
C5—H5 | 0.9300 | C33—H33B | 0.9700 |
C6—N2 | 1.462 (5) | C34—C48 | 1.510 (5) |
C7—N3 | 1.544 (5) | C34—C47 | 1.568 (5) |
C7—C8 | 1.558 (5) | C34—C35 | 1.584 (5) |
C7—H7A | 0.9700 | C35—C36 | 1.474 (5) |
C7—H7B | 0.9700 | C35—H35A | 0.9700 |
C8—C22 | 1.535 (5) | C35—H35B | 0.9700 |
C8—C9 | 1.558 (5) | C36—C37 | 1.569 (5) |
C8—C21 | 1.587 (4) | C36—H36A | 0.9700 |
C9—C10 | 1.486 (5) | C36—H36B | 0.9700 |
C9—H9A | 0.9700 | C37—C38 | 1.568 (5) |
C9—H9B | 0.9700 | C37—H37A | 0.9700 |
C10—C11 | 1.525 (5) | C37—H37B | 0.9700 |
C10—H10A | 0.9700 | C38—C39 | 1.503 (6) |
C10—H10B | 0.9700 | C38—C47 | 1.535 (5) |
C11—C12 | 1.598 (5) | C38—C49 | 1.554 (6) |
C11—H11A | 0.9700 | C39—C44 | 1.421 (5) |
C11—H11B | 0.9700 | C39—C40 | 1.423 (6) |
C12—C23 | 1.508 (5) | C40—C41 | 1.357 (6) |
C12—C13 | 1.539 (5) | C40—H40 | 0.9300 |
C12—C21 | 1.557 (5) | C41—C42 | 1.413 (5) |
C13—C14 | 1.342 (5) | C41—H41 | 0.9300 |
C13—C18 | 1.400 (4) | C42—C43 | 1.343 (5) |
C14—C15 | 1.424 (5) | C42—C50 | 1.570 (6) |
C14—H14 | 0.9300 | C43—C44 | 1.395 (5) |
C15—C16 | 1.405 (5) | C43—H43 | 0.9300 |
C15—H15 | 0.9300 | C44—C45 | 1.506 (5) |
C16—C17 | 1.412 (5) | C45—C46 | 1.500 (6) |
C16—C24 | 1.506 (5) | C45—H45A | 0.9700 |
C17—C18 | 1.399 (5) | C45—H45B | 0.9700 |
C17—H17 | 0.9300 | C46—C47 | 1.551 (5) |
C18—C19 | 1.558 (4) | C46—H46A | 0.9700 |
C19—C20 | 1.521 (4) | C46—H46B | 0.9700 |
C19—H19A | 0.9700 | C47—H47 | 0.9800 |
C19—H19B | 0.9700 | C48—H48A | 0.9600 |
C20—C21 | 1.550 (4) | C48—H48B | 0.9600 |
C20—H20A | 0.9700 | C48—H48C | 0.9600 |
C20—H20B | 0.9700 | C49—H49A | 0.9600 |
C21—H21 | 0.9800 | C49—H49B | 0.9600 |
C22—H22A | 0.9600 | C49—H49C | 0.9600 |
C22—H22B | 0.9600 | C50—C51 | 1.511 (6) |
C22—H22C | 0.9600 | C50—C52 | 1.512 (5) |
C23—H23A | 0.9600 | C50—H50 | 0.9800 |
C23—H23B | 0.9600 | C51—H51A | 0.9600 |
C23—H23C | 0.9600 | C51—H51B | 0.9600 |
C24—C26 | 1.507 (5) | C51—H51C | 0.9600 |
C24—C25 | 1.542 (5) | C52—H52A | 0.9600 |
C24—H24 | 0.9800 | C52—H52B | 0.9600 |
C25—H25A | 0.9600 | C52—H52C | 0.9600 |
C25—H25B | 0.9600 | N1—O1 | 1.217 (5) |
C25—H25C | 0.9600 | N1—O2 | 1.226 (5) |
C26—H26A | 0.9600 | N2—O4 | 1.204 (4) |
C26—H26B | 0.9600 | N2—O3 | 1.237 (4) |
C26—H26C | 0.9600 | N3—H3A | 0.86 (5) |
C27—N6 | 1.326 (5) | N4—O6 | 1.206 (4) |
C27—C28 | 1.404 (4) | N4—O5 | 1.247 (4) |
C27—C32 | 1.461 (6) | N5—O7 | 1.200 (5) |
C28—C29 | 1.403 (5) | N5—O8 | 1.273 (5) |
C28—H28 | 0.9300 | N6—H6 | 0.86 (5) |
N3—C1—C6 | 124.4 (4) | C31—C30—C29 | 122.4 (4) |
N3—C1—C2 | 121.9 (4) | C31—C30—N4 | 118.8 (4) |
C6—C1—C2 | 113.5 (3) | C29—C30—N4 | 118.8 (4) |
C3—C2—C1 | 125.3 (4) | C32—C31—C30 | 119.5 (4) |
C3—C2—H2 | 117.4 | C32—C31—H31 | 120.3 |
C1—C2—H2 | 117.4 | C30—C31—H31 | 120.3 |
C2—C3—C4 | 114.9 (4) | C31—C32—N5 | 116.3 (4) |
C2—C3—H3 | 122.6 | C31—C32—C27 | 121.3 (3) |
C4—C3—H3 | 122.6 | N5—C32—C27 | 122.3 (4) |
C5—C4—C3 | 123.4 (4) | N6—C33—C34 | 110.6 (3) |
C5—C4—N1 | 120.5 (4) | N6—C33—H33A | 109.5 |
C3—C4—N1 | 116.1 (4) | C34—C33—H33A | 109.5 |
C4—C5—C6 | 118.6 (4) | N6—C33—H33B | 109.5 |
C4—C5—H5 | 120.7 | C34—C33—H33B | 109.5 |
C6—C5—H5 | 120.7 | H33A—C33—H33B | 108.1 |
C5—C6—C1 | 124.1 (4) | C48—C34—C33 | 110.8 (3) |
C5—C6—N2 | 114.6 (3) | C48—C34—C47 | 113.9 (3) |
C1—C6—N2 | 121.2 (3) | C33—C34—C47 | 106.8 (3) |
N3—C7—C8 | 112.3 (3) | C48—C34—C35 | 112.5 (3) |
N3—C7—H7A | 109.1 | C33—C34—C35 | 106.2 (3) |
C8—C7—H7A | 109.1 | C47—C34—C35 | 106.2 (3) |
N3—C7—H7B | 109.1 | C36—C35—C34 | 114.0 (3) |
C8—C7—H7B | 109.1 | C36—C35—H35A | 108.8 |
H7A—C7—H7B | 107.9 | C34—C35—H35A | 108.8 |
C22—C8—C9 | 113.6 (3) | C36—C35—H35B | 108.8 |
C22—C8—C7 | 107.1 (3) | C34—C35—H35B | 108.8 |
C9—C8—C7 | 112.4 (3) | H35A—C35—H35B | 107.6 |
C22—C8—C21 | 114.6 (3) | C35—C36—C37 | 111.8 (3) |
C9—C8—C21 | 105.8 (3) | C35—C36—H36A | 109.3 |
C7—C8—C21 | 102.9 (3) | C37—C36—H36A | 109.3 |
C10—C9—C8 | 115.7 (3) | C35—C36—H36B | 109.3 |
C10—C9—H9A | 108.3 | C37—C36—H36B | 109.3 |
C8—C9—H9A | 108.3 | H36A—C36—H36B | 107.9 |
C10—C9—H9B | 108.3 | C38—C37—C36 | 111.0 (3) |
C8—C9—H9B | 108.3 | C38—C37—H37A | 109.4 |
H9A—C9—H9B | 107.4 | C36—C37—H37A | 109.4 |
C9—C10—C11 | 109.3 (3) | C38—C37—H37B | 109.4 |
C9—C10—H10A | 109.8 | C36—C37—H37B | 109.4 |
C11—C10—H10A | 109.8 | H37A—C37—H37B | 108.0 |
C9—C10—H10B | 109.8 | C39—C38—C47 | 109.5 (3) |
C11—C10—H10B | 109.8 | C39—C38—C49 | 106.3 (3) |
H10A—C10—H10B | 108.3 | C47—C38—C49 | 113.3 (3) |
C10—C11—C12 | 111.4 (3) | C39—C38—C37 | 108.6 (3) |
C10—C11—H11A | 109.3 | C47—C38—C37 | 109.3 (3) |
C12—C11—H11A | 109.3 | C49—C38—C37 | 109.7 (3) |
C10—C11—H11B | 109.3 | C44—C39—C40 | 115.7 (4) |
C12—C11—H11B | 109.3 | C44—C39—C38 | 120.9 (3) |
H11A—C11—H11B | 108.0 | C40—C39—C38 | 123.3 (3) |
C23—C12—C13 | 106.8 (3) | C41—C40—C39 | 124.4 (4) |
C23—C12—C21 | 118.2 (3) | C41—C40—H40 | 117.8 |
C13—C12—C21 | 109.3 (3) | C39—C40—H40 | 117.8 |
C23—C12—C11 | 108.7 (3) | C40—C41—C42 | 117.1 (4) |
C13—C12—C11 | 106.7 (3) | C40—C41—H41 | 121.5 |
C21—C12—C11 | 106.5 (3) | C42—C41—H41 | 121.5 |
C14—C13—C18 | 117.5 (3) | C43—C42—C41 | 120.4 (4) |
C14—C13—C12 | 122.1 (3) | C43—C42—C50 | 122.5 (3) |
C18—C13—C12 | 120.3 (3) | C41—C42—C50 | 116.8 (3) |
C13—C14—C15 | 123.5 (3) | C42—C43—C44 | 122.4 (4) |
C13—C14—H14 | 118.3 | C42—C43—H43 | 118.8 |
C15—C14—H14 | 118.3 | C44—C43—H43 | 118.8 |
C16—C15—C14 | 119.5 (3) | C43—C44—C39 | 119.1 (3) |
C16—C15—H15 | 120.2 | C43—C44—C45 | 119.5 (3) |
C14—C15—H15 | 120.2 | C39—C44—C45 | 121.4 (4) |
C15—C16—C17 | 116.9 (3) | C46—C45—C44 | 114.3 (3) |
C15—C16—C24 | 122.6 (3) | C46—C45—H45A | 108.7 |
C17—C16—C24 | 120.4 (3) | C44—C45—H45A | 108.7 |
C18—C17—C16 | 121.2 (3) | C46—C45—H45B | 108.7 |
C18—C17—H17 | 119.4 | C44—C45—H45B | 108.7 |
C16—C17—H17 | 119.4 | H45A—C45—H45B | 107.6 |
C17—C18—C13 | 121.3 (3) | C45—C46—C47 | 110.1 (3) |
C17—C18—C19 | 115.1 (3) | C45—C46—H46A | 109.6 |
C13—C18—C19 | 123.6 (3) | C47—C46—H46A | 109.6 |
C20—C19—C18 | 110.9 (3) | C45—C46—H46B | 109.6 |
C20—C19—H19A | 109.5 | C47—C46—H46B | 109.6 |
C18—C19—H19A | 109.5 | H46A—C46—H46B | 108.2 |
C20—C19—H19B | 109.5 | C38—C47—C46 | 107.7 (3) |
C18—C19—H19B | 109.5 | C38—C47—C34 | 118.8 (3) |
H19A—C19—H19B | 108.1 | C46—C47—C34 | 114.1 (3) |
C19—C20—C21 | 108.5 (3) | C38—C47—H47 | 105.0 |
C19—C20—H20A | 110.0 | C46—C47—H47 | 105.0 |
C21—C20—H20A | 110.0 | C34—C47—H47 | 105.0 |
C19—C20—H20B | 110.0 | C34—C48—H48A | 109.5 |
C21—C20—H20B | 110.0 | C34—C48—H48B | 109.5 |
H20A—C20—H20B | 108.4 | H48A—C48—H48B | 109.5 |
C20—C21—C12 | 107.7 (3) | C34—C48—H48C | 109.5 |
C20—C21—C8 | 116.1 (3) | H48A—C48—H48C | 109.5 |
C12—C21—C8 | 114.7 (3) | H48B—C48—H48C | 109.5 |
C20—C21—H21 | 105.8 | C38—C49—H49A | 109.5 |
C12—C21—H21 | 105.8 | C38—C49—H49B | 109.5 |
C8—C21—H21 | 105.8 | H49A—C49—H49B | 109.5 |
C8—C22—H22A | 109.5 | C38—C49—H49C | 109.5 |
C8—C22—H22B | 109.5 | H49A—C49—H49C | 109.5 |
H22A—C22—H22B | 109.5 | H49B—C49—H49C | 109.5 |
C8—C22—H22C | 109.5 | C51—C50—C52 | 105.8 (3) |
H22A—C22—H22C | 109.5 | C51—C50—C42 | 107.0 (3) |
H22B—C22—H22C | 109.5 | C52—C50—C42 | 117.7 (3) |
C12—C23—H23A | 109.5 | C51—C50—H50 | 108.7 |
C12—C23—H23B | 109.5 | C52—C50—H50 | 108.7 |
H23A—C23—H23B | 109.5 | C42—C50—H50 | 108.7 |
C12—C23—H23C | 109.5 | C50—C51—H51A | 109.5 |
H23A—C23—H23C | 109.5 | C50—C51—H51B | 109.5 |
H23B—C23—H23C | 109.5 | H51A—C51—H51B | 109.5 |
C16—C24—C26 | 113.2 (3) | C50—C51—H51C | 109.5 |
C16—C24—C25 | 108.8 (3) | H51A—C51—H51C | 109.5 |
C26—C24—C25 | 108.3 (3) | H51B—C51—H51C | 109.5 |
C16—C24—H24 | 108.9 | C50—C52—H52A | 109.5 |
C26—C24—H24 | 108.9 | C50—C52—H52B | 109.5 |
C25—C24—H24 | 108.9 | H52A—C52—H52B | 109.5 |
C24—C25—H25A | 109.5 | C50—C52—H52C | 109.5 |
C24—C25—H25B | 109.5 | H52A—C52—H52C | 109.5 |
H25A—C25—H25B | 109.5 | H52B—C52—H52C | 109.5 |
C24—C25—H25C | 109.5 | O1—N1—O2 | 122.1 (3) |
H25A—C25—H25C | 109.5 | O1—N1—C4 | 120.1 (4) |
H25B—C25—H25C | 109.5 | O2—N1—C4 | 117.8 (4) |
C24—C26—H26A | 109.5 | O4—N2—O3 | 121.2 (3) |
C24—C26—H26B | 109.5 | O4—N2—C6 | 120.9 (3) |
H26A—C26—H26B | 109.5 | O3—N2—C6 | 117.4 (3) |
C24—C26—H26C | 109.5 | C1—N3—C7 | 130.3 (3) |
H26A—C26—H26C | 109.5 | C1—N3—H3A | 115 (3) |
H26B—C26—H26C | 109.5 | C7—N3—H3A | 115 (3) |
N6—C27—C28 | 121.2 (3) | O6—N4—O5 | 118.7 (3) |
N6—C27—C32 | 122.2 (3) | O6—N4—C30 | 121.2 (3) |
C28—C27—C32 | 116.5 (3) | O5—N4—C30 | 120.0 (4) |
C29—C28—C27 | 121.9 (3) | O7—N5—O8 | 122.5 (3) |
C29—C28—H28 | 119.1 | O7—N5—C32 | 120.0 (4) |
C27—C28—H28 | 119.1 | O8—N5—C32 | 117.2 (3) |
C30—C29—C28 | 118.1 (3) | C27—N6—C33 | 125.6 (3) |
C30—C29—H29 | 120.9 | C27—N6—H6 | 117 (3) |
C28—C29—H29 | 120.9 | C33—N6—H6 | 117 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O4 | 0.86 (5) | 1.95 (5) | 2.650 (4) | 137 (4) |
N6—H6···O8 | 0.86 (5) | 1.99 (5) | 2.643 (4) | 132 (4) |
C10—H10A···O5i | 0.97 | 2.24 | 3.078 (5) | 144 |
C23—H23B···O5i | 0.96 | 2.46 | 3.242 (5) | 139 |
C41—H41···O8ii | 0.93 | 2.55 | 3.435 (5) | 159 |
Symmetry codes: (i) −x+1, y+1/2, −z+2; (ii) −x+2, y−1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C26H33N3O4 |
Mr | 451.55 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 291 |
a, b, c (Å) | 14.119 (7), 23.574 (12), 7.309 (4) |
β (°) | 99.191 (9) |
V (Å3) | 2402 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.26 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.98, 0.98 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15350, 6027, 4715 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.674 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.139, 1.07 |
No. of reflections | 6027 |
No. of parameters | 609 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.19, −0.19 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O4 | 0.86 (5) | 1.95 (5) | 2.650 (4) | 137 (4) |
N6—H6···O8 | 0.86 (5) | 1.99 (5) | 2.643 (4) | 132 (4) |
C10—H10A···O5i | 0.97 | 2.24 | 3.078 (5) | 144 |
C23—H23B···O5i | 0.96 | 2.46 | 3.242 (5) | 139 |
C41—H41···O8ii | 0.93 | 2.55 | 3.435 (5) | 159 |
Symmetry codes: (i) −x+1, y+1/2, −z+2; (ii) −x+2, y−1/2, −z. |
Acknowledgements
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
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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).