organic compounds
(7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,-9,10,10a-octahydrophenanthren-1-yl)methanaminium 4-toluenesulfonate
aCollege of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, People's Republic of China
*Correspondence e-mail: actae@googlegroups.com
In the title compound, C20H32N+·C7H7O3S−, the configurations of the two chiral centers observed in the protonated cation are consistent with previous reports. In the weak intermolecular N—H⋯O hydrogen bonds link ions into chains which develop along the a axis. The isopropyl group and four CH groups of the attached benzene ring are disordered approximately equally over two positions.
Related literature
For related literature, see: Gottstein & Cheney (1965); Rao et al. (2006); Tao (1993).
Experimental
Crystal data
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Data collection: SMART (Bruker, 2002); cell SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP3 (Farrugia, 1997) and XP in SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808010210/dn2336sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010210/dn2336Isup2.hkl
The title compound was synthesized according to the literature method(Gottstein & Cheney, 1965, Tao, 1993).
All H atoms attached to C atoms and N atom were fixed geometrically and treated as riding with C—H = 0.98 Å (methine), 0.97 Å(methylene), 0.96Å(methyl) or 0.93Å (aromatic) and N—H = 0.89Å with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(Cmethyl, N).
The isopropyl group and part of the ring to which it is attached is disordered over two positions as indicated by very elongated thermal ellipsoids. This disorder was treated using the PART and SADI instruction available in SHELXL97 (Sheldrick, 2008). The ratio between the two disordered fragments has been initialy obtained by refining the occupancy factor using the FVAR instruction with an overall isotropic thermal parameter. The ratio of the occupancy factor was found to be 0.53/0.47. Once correctly defined, the occupancy factors were fixed and a full
using restraints on C-C distances (SADI) and UIJ (SIMU, DELU) was carried out.Data collection: SMART (Bruker, 2002); cell
SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-32 (Farrugia, 1998) and XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C20H32N+·C7H7O3S− | F(000) = 992 |
Mr = 457.65 | Dx = 1.170 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5550 reflections |
a = 5.9954 (2) Å | θ = 2.4–21.4° |
b = 11.7039 (5) Å | µ = 0.15 mm−1 |
c = 37.0381 (13) Å | T = 296 K |
V = 2598.95 (17) Å3 | Box, colourless |
Z = 4 | 0.40 × 0.30 × 0.30 mm |
Bruker SMART CCD area-detector diffractometer | 5925 independent reflections |
Radiation source: fine-focus sealed tube | 4346 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ϕ and ω scans | θmax = 27.5°, θmin = 1.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −7→7 |
Tmin = 0.942, Tmax = 0.956 | k = −15→10 |
22386 measured reflections | l = −45→48 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.139 | w = 1/[σ2(Fo2) + (0.0817P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
5925 reflections | Δρmax = 0.22 e Å−3 |
360 parameters | Δρmin = −0.36 e Å−3 |
204 restraints | Absolute structure: Flack (1983), 2489 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.03 (8) |
C20H32N+·C7H7O3S− | V = 2598.95 (17) Å3 |
Mr = 457.65 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.9954 (2) Å | µ = 0.15 mm−1 |
b = 11.7039 (5) Å | T = 296 K |
c = 37.0381 (13) Å | 0.40 × 0.30 × 0.30 mm |
Bruker SMART CCD area-detector diffractometer | 5925 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 4346 reflections with I > 2σ(I) |
Tmin = 0.942, Tmax = 0.956 | Rint = 0.029 |
22386 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.139 | Δρmax = 0.22 e Å−3 |
S = 1.05 | Δρmin = −0.36 e Å−3 |
5925 reflections | Absolute structure: Flack (1983), 2489 Friedel pairs |
360 parameters | Absolute structure parameter: 0.03 (8) |
204 restraints |
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 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 | Occ. (<1) | |
C1 | 0.4813 (5) | 0.45313 (18) | 0.84444 (6) | 0.0648 (6) | |
H1A | 0.5164 | 0.5149 | 0.8279 | 0.078* | |
H1B | 0.3210 | 0.4529 | 0.8481 | 0.078* | |
C2 | 0.5952 (5) | 0.4754 (2) | 0.88024 (6) | 0.0714 (7) | |
H2A | 0.5444 | 0.5479 | 0.8899 | 0.086* | |
H2B | 0.7551 | 0.4804 | 0.8766 | 0.086* | |
C3 | 0.5442 (4) | 0.38020 (18) | 0.90724 (6) | 0.0596 (6) | |
H3A | 0.6241 | 0.3956 | 0.9295 | 0.072* | |
H3B | 0.3860 | 0.3813 | 0.9127 | 0.072* | |
C4 | 0.6073 (3) | 0.26118 (18) | 0.89395 (6) | 0.0513 (5) | |
C5 | 0.5098 (3) | 0.24264 (17) | 0.85538 (5) | 0.0512 (5) | |
H5 | 0.3478 | 0.2425 | 0.8589 | 0.061* | |
C6 | 0.5598 (5) | 0.1269 (2) | 0.83848 (7) | 0.0723 (7) | |
H6A | 0.7071 | 0.1275 | 0.8277 | 0.087* | |
H6B | 0.5562 | 0.0678 | 0.8568 | 0.087* | |
C7 | 0.3844 (6) | 0.1028 (3) | 0.80977 (8) | 0.0937 (10) | |
H7A | 0.4337 | 0.0386 | 0.7952 | 0.112* | |
H7B | 0.2467 | 0.0806 | 0.8216 | 0.112* | |
C8 | 0.3379 (5) | 0.2025 (3) | 0.78531 (7) | 0.0763 (8) | |
C9 | 0.4075 (4) | 0.3128 (2) | 0.79388 (6) | 0.0643 (6) | |
C10 | 0.5512 (4) | 0.3390 (2) | 0.82710 (6) | 0.0557 (5) | |
C11A | 0.354 (6) | 0.4122 (15) | 0.7717 (7) | 0.073 (4) | 0.47 |
H11A | 0.4093 | 0.4832 | 0.7787 | 0.087* | 0.47 |
C12A | 0.2225 (19) | 0.4056 (6) | 0.7397 (3) | 0.065 (2) | 0.47 |
H12A | 0.1884 | 0.4708 | 0.7265 | 0.078* | 0.47 |
C13A | 0.1461 (16) | 0.2979 (8) | 0.7289 (2) | 0.061 (2) | 0.47 |
C14A | 0.210 (2) | 0.2074 (7) | 0.7520 (3) | 0.066 (2) | 0.47 |
H14A | 0.1599 | 0.1364 | 0.7442 | 0.079* | 0.47 |
C18A | 0.0100 (12) | 0.2855 (7) | 0.69557 (16) | 0.0750 (17) | 0.47 |
H18A | −0.0248 | 0.3610 | 0.6856 | 0.090* | 0.47 |
C19A | 0.108 (2) | 0.2104 (16) | 0.6668 (4) | 0.164 (8) | 0.47 |
H19A | 0.1331 | 0.1354 | 0.6764 | 0.246* | 0.47 |
H19B | 0.2467 | 0.2422 | 0.6587 | 0.246* | 0.47 |
H19C | 0.0062 | 0.2056 | 0.6468 | 0.246* | 0.47 |
C20A | −0.199 (3) | 0.2203 (19) | 0.7017 (7) | 0.178 (10) | 0.47 |
H20A | −0.1629 | 0.1465 | 0.7114 | 0.268* | 0.47 |
H20B | −0.2766 | 0.2114 | 0.6793 | 0.268* | 0.47 |
H20C | −0.2912 | 0.2610 | 0.7185 | 0.268* | 0.47 |
C11B | 0.344 (6) | 0.3896 (14) | 0.7680 (6) | 0.076 (4) | 0.53 |
H11B | 0.3803 | 0.4664 | 0.7707 | 0.091* | 0.53 |
C12B | 0.2278 (18) | 0.3544 (7) | 0.7386 (3) | 0.069 (2) | 0.53 |
H12B | 0.1855 | 0.4096 | 0.7218 | 0.083* | 0.53 |
C13B | 0.1685 (14) | 0.2434 (7) | 0.7317 (3) | 0.068 (2) | 0.53 |
C14B | 0.223 (2) | 0.1613 (6) | 0.7559 (2) | 0.068 (2) | 0.53 |
H14B | 0.1867 | 0.0847 | 0.7529 | 0.082* | 0.53 |
C18B | 0.0331 (11) | 0.2128 (8) | 0.69788 (16) | 0.0893 (19) | 0.53 |
H18B | 0.0283 | 0.1295 | 0.6954 | 0.107* | 0.53 |
C19B | 0.162 (2) | 0.2641 (14) | 0.6647 (3) | 0.136 (6) | 0.53 |
H19D | 0.1625 | 0.3460 | 0.6664 | 0.205* | 0.53 |
H19E | 0.0897 | 0.2412 | 0.6428 | 0.205* | 0.53 |
H19F | 0.3129 | 0.2365 | 0.6648 | 0.205* | 0.53 |
C20B | −0.2109 (16) | 0.2584 (13) | 0.7026 (4) | 0.094 (3) | 0.53 |
H20D | −0.2664 | 0.2366 | 0.7259 | 0.141* | 0.53 |
H20E | −0.3045 | 0.2264 | 0.6842 | 0.141* | 0.53 |
H20F | −0.2113 | 0.3402 | 0.7006 | 0.141* | 0.53 |
C15 | 0.4892 (4) | 0.17224 (18) | 0.91797 (6) | 0.0576 (5) | |
H15A | 0.3300 | 0.1765 | 0.9134 | 0.069* | |
H15B | 0.5387 | 0.0967 | 0.9108 | 0.069* | |
C16 | 0.8591 (4) | 0.2415 (3) | 0.89661 (8) | 0.0758 (7) | |
H16A | 0.9361 | 0.3014 | 0.8840 | 0.114* | |
H16B | 0.8960 | 0.1692 | 0.8860 | 0.114* | |
H16C | 0.9031 | 0.2417 | 0.9215 | 0.114* | |
C17 | 0.7940 (4) | 0.3494 (3) | 0.81380 (7) | 0.0770 (8) | |
H17A | 0.8009 | 0.4033 | 0.7943 | 0.115* | |
H17B | 0.8453 | 0.2762 | 0.8056 | 0.115* | |
H17C | 0.8870 | 0.3752 | 0.8333 | 0.115* | |
C31 | 0.8536 (4) | −0.25930 (19) | 1.06820 (6) | 0.0626 (6) | |
C32 | 1.0535 (4) | −0.25420 (19) | 1.04994 (6) | 0.0678 (7) | |
H32 | 1.1605 | −0.3103 | 1.0540 | 0.081* | |
C33 | 1.0981 (4) | −0.16706 (19) | 1.02573 (6) | 0.0598 (6) | |
H33 | 1.2343 | −0.1647 | 1.0137 | 0.072* | |
C34 | 0.9414 (3) | −0.08452 (17) | 1.01948 (6) | 0.0506 (5) | |
C35 | 0.7373 (4) | −0.08909 (19) | 1.03689 (6) | 0.0607 (6) | |
H35 | 0.6292 | −0.0339 | 1.0324 | 0.073* | |
C36 | 0.6962 (4) | −0.1768 (2) | 1.06106 (7) | 0.0667 (6) | |
H36 | 0.5590 | −0.1801 | 1.0727 | 0.080* | |
C37 | 0.8088 (7) | −0.3537 (2) | 1.09495 (8) | 0.0913 (10) | |
H37A | 0.7348 | −0.4158 | 1.0830 | 0.137* | |
H37B | 0.7157 | −0.3253 | 1.1140 | 0.137* | |
H37C | 0.9475 | −0.3801 | 1.1049 | 0.137* | |
N1 | 0.5270 (3) | 0.18534 (15) | 0.95701 (5) | 0.0565 (4) | |
H1C | 0.6678 | 0.1678 | 0.9622 | 0.085* | |
H1D | 0.4359 | 0.1389 | 0.9690 | 0.085* | |
H1E | 0.5001 | 0.2573 | 0.9634 | 0.085* | |
O1 | 0.8894 (4) | 0.12792 (13) | 1.00269 (5) | 0.0828 (6) | |
O2 | 0.9025 (4) | −0.00303 (15) | 0.95411 (4) | 0.0818 (5) | |
O3 | 1.2366 (3) | 0.0371 (2) | 0.98855 (8) | 0.1196 (10) | |
S1 | 0.99852 (11) | 0.02625 (5) | 0.988456 (17) | 0.06402 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0798 (17) | 0.0532 (12) | 0.0612 (13) | −0.0036 (13) | 0.0047 (13) | 0.0070 (10) |
C2 | 0.0970 (19) | 0.0557 (13) | 0.0615 (14) | −0.0134 (14) | 0.0079 (13) | 0.0041 (11) |
C3 | 0.0707 (15) | 0.0544 (11) | 0.0537 (12) | −0.0089 (11) | 0.0018 (11) | 0.0018 (9) |
C4 | 0.0412 (10) | 0.0523 (11) | 0.0604 (12) | −0.0054 (10) | 0.0072 (9) | 0.0037 (10) |
C5 | 0.0432 (10) | 0.0515 (10) | 0.0589 (12) | −0.0003 (10) | 0.0120 (10) | −0.0024 (9) |
C6 | 0.086 (2) | 0.0623 (14) | 0.0682 (15) | 0.0065 (13) | 0.0188 (14) | −0.0090 (11) |
C7 | 0.111 (2) | 0.0824 (19) | 0.088 (2) | −0.0165 (19) | 0.0141 (19) | −0.0295 (17) |
C8 | 0.0679 (16) | 0.100 (2) | 0.0611 (16) | −0.0084 (16) | 0.0129 (12) | −0.0205 (15) |
C9 | 0.0513 (12) | 0.0902 (18) | 0.0513 (13) | −0.0044 (13) | 0.0133 (11) | −0.0015 (12) |
C10 | 0.0511 (13) | 0.0661 (13) | 0.0499 (12) | −0.0036 (10) | 0.0088 (9) | 0.0011 (10) |
C11A | 0.064 (7) | 0.101 (7) | 0.053 (6) | 0.003 (7) | −0.002 (4) | 0.007 (6) |
C12A | 0.071 (4) | 0.061 (4) | 0.062 (4) | 0.009 (5) | 0.006 (3) | 0.011 (4) |
C13A | 0.057 (4) | 0.071 (6) | 0.055 (4) | 0.009 (4) | 0.011 (3) | 0.000 (4) |
C14A | 0.077 (5) | 0.049 (5) | 0.071 (5) | −0.013 (5) | 0.013 (4) | −0.004 (5) |
C18A | 0.076 (4) | 0.082 (4) | 0.068 (4) | 0.014 (4) | −0.008 (3) | −0.006 (3) |
C19A | 0.113 (10) | 0.257 (18) | 0.121 (10) | 0.111 (12) | −0.046 (8) | −0.101 (10) |
C20A | 0.162 (18) | 0.182 (19) | 0.191 (15) | −0.089 (14) | −0.055 (12) | −0.012 (13) |
C11B | 0.069 (6) | 0.098 (7) | 0.060 (6) | −0.014 (6) | 0.008 (5) | −0.001 (5) |
C12B | 0.079 (5) | 0.069 (5) | 0.058 (4) | 0.021 (5) | −0.001 (3) | 0.002 (5) |
C13B | 0.061 (3) | 0.077 (6) | 0.067 (4) | 0.013 (4) | 0.003 (3) | −0.010 (4) |
C14B | 0.083 (4) | 0.058 (4) | 0.063 (4) | −0.014 (5) | 0.013 (3) | −0.011 (4) |
C18B | 0.091 (5) | 0.100 (5) | 0.077 (4) | 0.023 (5) | −0.012 (3) | −0.015 (4) |
C19B | 0.109 (7) | 0.253 (15) | 0.047 (4) | −0.027 (8) | −0.010 (4) | −0.024 (6) |
C20B | 0.068 (5) | 0.124 (8) | 0.091 (6) | 0.002 (5) | −0.020 (4) | −0.005 (5) |
C15 | 0.0590 (13) | 0.0555 (11) | 0.0583 (12) | −0.0110 (11) | 0.0052 (11) | 0.0063 (9) |
C16 | 0.0469 (13) | 0.0997 (19) | 0.0810 (17) | 0.0028 (14) | 0.0065 (11) | 0.0155 (16) |
C17 | 0.0577 (15) | 0.107 (2) | 0.0661 (15) | −0.0105 (14) | 0.0169 (12) | 0.0118 (15) |
C31 | 0.0839 (17) | 0.0460 (11) | 0.0578 (13) | −0.0055 (12) | −0.0035 (11) | 0.0019 (10) |
C32 | 0.0838 (18) | 0.0469 (11) | 0.0728 (15) | 0.0147 (12) | −0.0042 (13) | 0.0028 (11) |
C33 | 0.0549 (13) | 0.0567 (13) | 0.0679 (14) | 0.0115 (10) | 0.0036 (11) | 0.0048 (10) |
C34 | 0.0461 (11) | 0.0456 (10) | 0.0601 (12) | −0.0033 (9) | −0.0021 (9) | 0.0019 (9) |
C35 | 0.0482 (12) | 0.0524 (12) | 0.0816 (16) | 0.0031 (10) | −0.0028 (12) | 0.0089 (11) |
C36 | 0.0612 (14) | 0.0653 (14) | 0.0735 (15) | −0.0078 (12) | 0.0075 (12) | 0.0065 (12) |
C37 | 0.137 (3) | 0.0662 (16) | 0.0708 (17) | −0.0128 (17) | −0.0046 (18) | 0.0159 (13) |
N1 | 0.0503 (10) | 0.0550 (9) | 0.0641 (11) | −0.0047 (8) | 0.0032 (9) | 0.0131 (8) |
O1 | 0.1152 (16) | 0.0473 (9) | 0.0859 (12) | −0.0018 (10) | −0.0308 (11) | 0.0102 (8) |
O2 | 0.1068 (14) | 0.0746 (11) | 0.0641 (10) | 0.0038 (10) | −0.0039 (10) | 0.0154 (9) |
O3 | 0.0561 (11) | 0.1249 (19) | 0.178 (2) | −0.0252 (12) | −0.0091 (13) | 0.0906 (18) |
S1 | 0.0572 (3) | 0.0545 (3) | 0.0804 (4) | −0.0071 (3) | −0.0065 (3) | 0.0208 (3) |
C1—C2 | 1.514 (3) | C11B—H11B | 0.9300 |
C1—C10 | 1.540 (3) | C12B—C13B | 1.371 (9) |
C1—H1A | 0.9700 | C12B—H12B | 0.9300 |
C1—H1B | 0.9700 | C13B—C14B | 1.353 (8) |
C2—C3 | 1.528 (3) | C13B—C18B | 1.535 (10) |
C2—H2A | 0.9700 | C14B—H14B | 0.9300 |
C2—H2B | 0.9700 | C18B—C20B | 1.566 (11) |
C3—C4 | 1.525 (3) | C18B—C19B | 1.571 (12) |
C3—H3A | 0.9700 | C18B—H18B | 0.9800 |
C3—H3B | 0.9700 | C19B—H19D | 0.9600 |
C4—C16 | 1.530 (3) | C19B—H19E | 0.9600 |
C4—C15 | 1.542 (3) | C19B—H19F | 0.9600 |
C4—C5 | 1.559 (3) | C20B—H20D | 0.9600 |
C5—C6 | 1.522 (3) | C20B—H20E | 0.9600 |
C5—C10 | 1.559 (3) | C20B—H20F | 0.9600 |
C5—H5 | 0.9800 | C15—N1 | 1.472 (3) |
C6—C7 | 1.522 (4) | C15—H15A | 0.9700 |
C6—H6A | 0.9700 | C15—H15B | 0.9700 |
C6—H6B | 0.9700 | C16—H16A | 0.9600 |
C7—C8 | 1.504 (4) | C16—H16B | 0.9600 |
C7—H7A | 0.9700 | C16—H16C | 0.9600 |
C7—H7B | 0.9700 | C17—H17A | 0.9600 |
C8—C14B | 1.375 (9) | C17—H17B | 0.9600 |
C8—C9 | 1.393 (4) | C17—H17C | 0.9600 |
C8—C14A | 1.455 (10) | C31—C36 | 1.376 (3) |
C9—C11B | 1.368 (11) | C31—C32 | 1.377 (4) |
C9—C11A | 1.460 (12) | C31—C37 | 1.508 (3) |
C9—C10 | 1.533 (3) | C32—C33 | 1.384 (3) |
C10—C17 | 1.542 (3) | C32—H32 | 0.9300 |
C11A—C12A | 1.425 (11) | C33—C34 | 1.367 (3) |
C11A—H11A | 0.9300 | C33—H33 | 0.9300 |
C12A—C13A | 1.400 (9) | C34—C35 | 1.384 (3) |
C12A—H12A | 0.9300 | C34—S1 | 1.766 (2) |
C13A—C14A | 1.412 (9) | C35—C36 | 1.384 (3) |
C13A—C18A | 1.488 (11) | C35—H35 | 0.9300 |
C14A—H14A | 0.9300 | C36—H36 | 0.9300 |
C18A—C20A | 1.482 (16) | C37—H37A | 0.9600 |
C18A—C19A | 1.501 (12) | C37—H37B | 0.9600 |
C18A—H18A | 0.9800 | C37—H37C | 0.9600 |
C19A—H19A | 0.9600 | N1—H1C | 0.8900 |
C19A—H19B | 0.9600 | N1—H1D | 0.8900 |
C19A—H19C | 0.9600 | N1—H1E | 0.8900 |
C20A—H20A | 0.9600 | O1—S1 | 1.457 (2) |
C20A—H20B | 0.9600 | O2—S1 | 1.4377 (19) |
C20A—H20C | 0.9600 | O3—S1 | 1.433 (2) |
C11B—C12B | 1.359 (11) | ||
C2—C1—C10 | 113.1 (2) | C11B—C12B—C13B | 124.7 (9) |
C2—C1—H1A | 109.0 | C11B—C12B—H12B | 117.7 |
C10—C1—H1A | 109.0 | C13B—C12B—H12B | 117.7 |
C2—C1—H1B | 109.0 | C14B—C13B—C12B | 119.2 (7) |
C10—C1—H1B | 109.0 | C14B—C13B—C18B | 120.2 (7) |
H1A—C1—H1B | 107.8 | C12B—C13B—C18B | 120.6 (8) |
C1—C2—C3 | 110.9 (2) | C13B—C14B—C8 | 113.4 (6) |
C1—C2—H2A | 109.5 | C13B—C14B—H14B | 123.3 |
C3—C2—H2A | 109.5 | C8—C14B—H14B | 123.3 |
C1—C2—H2B | 109.5 | C13B—C18B—C20B | 108.9 (7) |
C3—C2—H2B | 109.5 | C13B—C18B—C19B | 106.8 (8) |
H2A—C2—H2B | 108.0 | C20B—C18B—C19B | 114.6 (9) |
C4—C3—C2 | 113.92 (18) | C13B—C18B—H18B | 108.8 |
C4—C3—H3A | 108.8 | C20B—C18B—H18B | 108.8 |
C2—C3—H3A | 108.8 | C19B—C18B—H18B | 108.8 |
C4—C3—H3B | 108.8 | C18B—C19B—H19D | 109.5 |
C2—C3—H3B | 108.8 | C18B—C19B—H19E | 109.5 |
H3A—C3—H3B | 107.7 | H19D—C19B—H19E | 109.5 |
C3—C4—C16 | 111.2 (2) | C18B—C19B—H19F | 109.5 |
C3—C4—C15 | 108.46 (17) | H19D—C19B—H19F | 109.5 |
C16—C4—C15 | 108.3 (2) | H19E—C19B—H19F | 109.5 |
C3—C4—C5 | 109.27 (17) | C18B—C20B—H20D | 109.5 |
C16—C4—C5 | 114.08 (19) | C18B—C20B—H20E | 109.5 |
C15—C4—C5 | 105.23 (17) | H20D—C20B—H20E | 109.5 |
C6—C5—C4 | 115.28 (18) | C18B—C20B—H20F | 109.5 |
C6—C5—C10 | 109.66 (17) | H20D—C20B—H20F | 109.5 |
C4—C5—C10 | 117.08 (17) | H20E—C20B—H20F | 109.5 |
C6—C5—H5 | 104.4 | N1—C15—C4 | 115.21 (18) |
C4—C5—H5 | 104.4 | N1—C15—H15A | 108.5 |
C10—C5—H5 | 104.4 | C4—C15—H15A | 108.5 |
C7—C6—C5 | 108.5 (2) | N1—C15—H15B | 108.5 |
C7—C6—H6A | 110.0 | C4—C15—H15B | 108.5 |
C5—C6—H6A | 110.0 | H15A—C15—H15B | 107.5 |
C7—C6—H6B | 110.0 | C4—C16—H16A | 109.5 |
C5—C6—H6B | 110.0 | C4—C16—H16B | 109.5 |
H6A—C6—H6B | 108.4 | H16A—C16—H16B | 109.5 |
C8—C7—C6 | 113.9 (2) | C4—C16—H16C | 109.5 |
C8—C7—H7A | 108.8 | H16A—C16—H16C | 109.5 |
C6—C7—H7A | 108.8 | H16B—C16—H16C | 109.5 |
C8—C7—H7B | 108.8 | C10—C17—H17A | 109.5 |
C6—C7—H7B | 108.8 | C10—C17—H17B | 109.5 |
H7A—C7—H7B | 107.7 | H17A—C17—H17B | 109.5 |
C14B—C8—C9 | 130.9 (4) | C10—C17—H17C | 109.5 |
C14B—C8—C14A | 22.8 (3) | H17A—C17—H17C | 109.5 |
C9—C8—C14A | 108.3 (4) | H17B—C17—H17C | 109.5 |
C14B—C8—C7 | 107.4 (4) | C36—C31—C32 | 118.2 (2) |
C9—C8—C7 | 121.8 (2) | C36—C31—C37 | 121.2 (3) |
C14A—C8—C7 | 129.8 (4) | C32—C31—C37 | 120.6 (2) |
C11B—C9—C8 | 111.5 (7) | C31—C32—C33 | 121.2 (2) |
C11B—C9—C11A | 11.7 (14) | C31—C32—H32 | 119.4 |
C8—C9—C11A | 123.0 (7) | C33—C32—H32 | 119.4 |
C11B—C9—C10 | 125.9 (7) | C34—C33—C32 | 119.9 (2) |
C8—C9—C10 | 122.4 (2) | C34—C33—H33 | 120.1 |
C11A—C9—C10 | 114.5 (7) | C32—C33—H33 | 120.1 |
C9—C10—C1 | 110.8 (2) | C33—C34—C35 | 120.1 (2) |
C9—C10—C17 | 106.86 (19) | C33—C34—S1 | 119.73 (17) |
C1—C10—C17 | 108.8 (2) | C35—C34—S1 | 120.19 (17) |
C9—C10—C5 | 107.74 (19) | C34—C35—C36 | 119.2 (2) |
C1—C10—C5 | 107.70 (16) | C34—C35—H35 | 120.4 |
C17—C10—C5 | 115.0 (2) | C36—C35—H35 | 120.4 |
C12A—C11A—C9 | 123.0 (13) | C31—C36—C35 | 121.5 (2) |
C12A—C11A—H11A | 118.5 | C31—C36—H36 | 119.3 |
C9—C11A—H11A | 118.5 | C35—C36—H36 | 119.3 |
C13A—C12A—C11A | 117.8 (10) | C31—C37—H37A | 109.5 |
C13A—C12A—H12A | 121.1 | C31—C37—H37B | 109.5 |
C11A—C12A—H12A | 121.1 | H37A—C37—H37B | 109.5 |
C12A—C13A—C14A | 114.5 (7) | C31—C37—H37C | 109.5 |
C12A—C13A—C18A | 120.3 (7) | H37A—C37—H37C | 109.5 |
C14A—C13A—C18A | 125.3 (8) | H37B—C37—H37C | 109.5 |
C13A—C14A—C8 | 133.3 (7) | C15—N1—H1C | 109.5 |
C13A—C14A—H14A | 113.4 | C15—N1—H1D | 109.5 |
C8—C14A—H14A | 113.4 | H1C—N1—H1D | 109.5 |
C20A—C18A—C13A | 112.6 (11) | C15—N1—H1E | 109.5 |
C20A—C18A—C19A | 97.9 (13) | H1C—N1—H1E | 109.5 |
C13A—C18A—C19A | 115.6 (8) | H1D—N1—H1E | 109.5 |
C20A—C18A—H18A | 110.0 | O3—S1—O2 | 114.95 (16) |
C13A—C18A—H18A | 110.0 | O3—S1—O1 | 111.98 (17) |
C19A—C18A—H18A | 110.0 | O2—S1—O1 | 109.59 (11) |
C12B—C11B—C9 | 120.4 (12) | O3—S1—C34 | 104.85 (11) |
C12B—C11B—H11B | 119.8 | O2—S1—C34 | 108.85 (10) |
C9—C11B—H11B | 119.8 | O1—S1—C34 | 106.09 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1C···O1 | 0.89 | 2.06 | 2.835 (3) | 145 |
N1—H1D···O3i | 0.89 | 1.84 | 2.722 (3) | 173 |
N1—H1E···O1ii | 0.89 | 1.95 | 2.772 (3) | 152 |
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C20H32N+·C7H7O3S− |
Mr | 457.65 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 5.9954 (2), 11.7039 (5), 37.0381 (13) |
V (Å3) | 2598.95 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.15 |
Crystal size (mm) | 0.40 × 0.30 × 0.30 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.942, 0.956 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22386, 5925, 4346 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.139, 1.05 |
No. of reflections | 5925 |
No. of parameters | 360 |
No. of restraints | 204 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.36 |
Absolute structure | Flack (1983), 2489 Friedel pairs |
Absolute structure parameter | 0.03 (8) |
Computer programs: SMART (Bruker, 2002), SAINT-Plus (Bruker, 2003), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-32 (Farrugia, 1998) and XP in SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1C···O1 | 0.89 | 2.06 | 2.835 (3) | 145.3 |
N1—H1D···O3i | 0.89 | 1.84 | 2.722 (3) | 173.2 |
N1—H1E···O1ii | 0.89 | 1.95 | 2.772 (3) | 152.1 |
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, −z+2. |
Acknowledgements
This work was supported by the National Natural Science Foundation of China under grant No. 30771686.
References
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Dehydroabietylamine, a unique synthetic primary amine having a three fused rings structure, is obtained as part of a mixture of amines prepared by the hydrogenation of rosin acid nitrile.
The cation and anion are linked by N-H···O hydrogen bond (Table 1, Fig.1). The R and S absolute configuration observed at C4 and C10 has been determined by the refinement of the Flack parameter (Flack, 1983). These absolute configurations agree with previous reports(Rao et al., 2006, Tao, 1993).
Further N—H···O hydrogen bonds between the amine group and the O atoms of the SO3 group, link molecules into chains developing along the a axis (Table 1).