(7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,-9,10,10a-octa­hydro­phenanthren-1-yl)­methanaminium 4-toluene­sulfonate

Li, Y.; Zeng, T.; Huang, D.

doi:10.1107/S1600536808010210

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o872

doi:10.1107/S1600536808010210

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(7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,-9,10,10a-octahydrophenanthren-1-yl)methanaminium 4-toluenesulfonate

Yong Li,^a Tao Zeng ^a ^* and Dao-zhan Huang ^a

^aCollege of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, People's Republic of China
^*Correspondence e-mail: actae@googlegroups.com

(Received 6 April 2008; accepted 14 April 2008; online 18 April 2008)

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 crystal structure, 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

C₂₀H₃₂N⁺·C₇H₇O₃S⁻
M_r = 457.65
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.9954 (2) Å
b = 11.7039 (5) Å
c = 37.0381 (13) Å
V = 2598.95 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 296 (2) K
0.40 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.942, T_max = 0.956
22386 measured reflections
5925 independent reflections
4346 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.139
S = 1.05
5925 reflections
360 parameters
204 restraints
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.35 e Å⁻³
Absolute structure: Flack (1983 ), 2489 Friedel pairs
Flack parameter: 0.03 (8)

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010210/dn2336sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010210/dn2336Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

For related literature, see: Gottstein & Cheney (1965); Rao et al. (2006); Tao (1993).

Experimental top

The title compound was synthesized according to the literature method(Gottstein & Cheney, 1965, Tao, 1993).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: 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).

Figures top

Fig. 1. A view of the title compound with the atom-labelling scheme. Thermal ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Only one aprt of the disordered moiety is represented for clarity. H bond is shown as dashed line.

(7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1- yl)methanaminium 4-toluenesulfonate top

Crystal data top

C₂₀H₃₂N⁺·C₇H₇O₃S⁻	F(000) = 992
M_r = 457.65	D_x = 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

Data collection top

Bruker SMART CCD area-detector diffractometer	5925 independent reflections
Radiation source: fine-focus sealed tube	4346 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→7
T_min = 0.942, T_max = 0.956	k = −15→10
22386 measured reflections	l = −45→48

Refinement top

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(F_o²) + (0.0817P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
5925 reflections	Δρ_max = 0.22 e Å⁻³
360 parameters	Δρ_min = −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)

Crystal data top

C₂₀H₃₂N⁺·C₇H₇O₃S⁻	V = 2598.95 (17) Å³
M_r = 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

Data collection top

Bruker SMART CCD area-detector diffractometer	5925 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	4346 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.956	R_int = 0.029
22386 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.139	Δρ_max = 0.22 e Å⁻³
S = 1.05	Δρ_min = −0.36 e Å⁻³
5925 reflections	Absolute structure: Flack (1983), 2489 Friedel pairs
360 parameters	Absolute structure parameter: 0.03 (8)
204 restraints

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 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

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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⁻
M_r	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)
T_min, T_max	0.942, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	22386, 5925, 4346
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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

Bruker (2000). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2002). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gottstein, W. J. & Cheney, L. C. (1965). J. Org. Chem. 30, 2072–2073. CrossRef CAS Web of Science Google Scholar
Rao, X.-P., Song, Z.-Q., Gong, Y., Yao, X.-J. & Shang, S.-B. (2006). Acta Cryst. E62, o3450–o3451. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tao, Z. (1993). Chem. Ind. Times, 21, 9–16. Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(7-Iso­propyl-1,4a-di­methyl-1,2,3,4,4a,-9,10,10a-octa­hydro­phenanthren-1-yl)­methanaminium 4-toluene­sulfonate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,-9,10,10a-octahydrophenanthren-1-yl)methanaminium 4-toluenesulfonate