1-(1,5-Dimethyl­hexyl)-3a,5b,12a,14a-tetra­methyl-2,3,3a,4,5,5a,5b,11,12,13,14,14a-dodeca­hydro-1H,12aH-cyclo­penta­[1,2]phenanthro[7,8-b]indole

López-Rodríguez, M.; Mazoir, N.; Daoubi, M.; Reina, M.; Benharref, A.

doi:10.1107/S1600536807053913

1-(1,5-Dimethylhexyl)-3a,5b,12a,14a-tetramethyl-2,3,3a,4,5,5a,5b,11,12,13,14,14a-dodecahydro-1H,12aH-cyclopenta[1,2]phenanthro[7,8-b]indole

M. López-Rodríguez, N. Mazoir, M. Daoubi, M. Reina and A. Benharref

The title compound, C₃₅H₅₁N, is a semi-synthesized derivative obtained from 4α,14α-dimethyl-5α-cholest-8-en-3β-ol, a major triterpene isolated from Euphorbia officinarum latex. The molecular structure was established by ¹H and ¹³C NMR spectroscopy and confirmed as having the β stereochemistry at the new C11b stereocenter by single-crystal X-ray diffraction. The planar indole group is folded over the extended tetracyclic perhydrocyclopentanephenanthrene triterpene skeleton. There are no π–π interactions between the indole ring systems.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053913/hg2320sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053913/hg2320Isup2.hkl Contains datablock I

CCDC reference: 673090

checkCIF report

Key indicators

Single-crystal X-ray study
T = 170 K
Mean (C-C) = 0.006 Å
R factor = 0.075
wR factor = 0.176
Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       9.76 Ratio

Author Response: It has not been possible to improve the result of the refinements in spite of the different approaches that we have carried out : measuring of different crystals, low temperature, study of models of disorder, etc. We think that there are two factors that could explain this fact, on one hand the low quality of the available crystals, on the other hand the hight thermal motion of the long lateral chain of the perhydrocyclopentanophenantrene moiety, particularly, the isopropyl terminal group. In this sense the behavior of the present compound it is not very different from those mentioned in the related bibliography and that were published in this journal.

PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...      10.00 Ratio

Author Response: Same as above


Alert level C
PLAT213_ALERT_2_C Atom C7"     has ADP max/min Ratio .............       3.10 prola
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5"    -   C7"     ..       6.86 su
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C5"    -   C6"    ...       1.43 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C5"    -   C7"    ...       1.43 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         22

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.00
           From the CIF: _reflns_number_total               3625
           Count of symmetry unique reflns         3659
           Completeness (_total/calc)             99.07%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1'    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1"    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4B    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11B   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11C   = .          R

   2 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   8 ALERT level G = General alerts; check

   7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The title compound (II) (Scheme 1) was obtained by transformation of the natural triterpene: 4α,14α-dimethyl-5α-cholest-8-en-3β-ol(I) (Scheme1). In the course of the reaction the α stereochemistry at C4 in (I) changes to β at the C11b in (II), because the new C11a—C11b bond is preferably developed through the less crowdy α face of (I). However, that of the remaining stereocenters remains unchanged. The above-mentioned, together with the known absolute stereochemistry of (I) allows us to assign the absolute configuration of (II) as 1(R),1'(R),1"(R),2(R),4 b(S),C11b(R), C11c(R). For structural details of related hemisynthesized derivatives from moroccan natural products, see:Auhmani et al. (2005); Mazoir, Giorgi & Benharrei (2005); Mazoir, Giorgi & Auhmani (2005); Mazoir et al. (2006).

Related literature top

For related literature, see: Auhmani et al. (2005); Mazoir et al. (2006); Mazoir, Giorgi & Auhmani (2005); Mazoir, Giorgi & Benharrei (2005).

Experimental top

The oxidation of the natural triterpene 4α,14α-dimethyl-5α-cholest-8-en-3β-ol, during 1 h with 3 equivalents of chromic anhydride (CrO₃) in acetone at 273 K followed by heating under reflux with 1 equivalent of phenylhydrazine in the presence of acetic acid afforded, after chromatographic purification on silica gel column, the title compound, with an overall 92% yield. Crystals were obtained by evaporation from methanol solution at 277 K. Spectroscopic analysis: ¹H NMR (500 MHz, CDCl3, δ (p.p.m.): 7.60 (H8,d,J=7.7 Hz),7.33 (H9,t, J1=15.1 Hz; J2=7.6 Hz),7.18 (H10,t, J1=14.8; J2=7.4 Hz, 7.43 (H11,d, J=7.4 Hz), 0.85 (H6'', d, J =2.3 Hz), 0.86 (H7'',J=2.3 Hz), 0.87 (H8'', d, J=6.3 Hz), 0.72 (H9'', s), 1.31 (H10'', s), 1.33 (H11'', s), 0.75 (H12'', s);¹³C NMR (125 MHz, CDCl3, δ (p.p.m.): 49.3 (C1), 44.3 (C2),25.7 (C3), 27.9 (C4),135.2 (C4a), 36.3 (C4b), 39.4 (C5), 40.8 (C6), 192.2 (C6a),154.5 (C7a), 127.9 (C8), 123.4 (C9), 120.7 (C10), 124.8 (C11), 147.9 (C11a),57.6 (C11b), 50.4 (C11c), 21.6 (C12), 20.1 (C13), 133.2 (C13a), 51.4 (C1'),25.6 (C2'), 23.9 (C3'), 35.3 (C1''), 30.7 (C2''), 30.8 (C3''),34.6 (C4''),28.0 (C5''), 22.4 (C6''), 22.7 (C7''), 19.0 (C8''),15.6 (C9''), 18.6 (C10''),24.1 (C11''), 16.2 (C12'').

Computing details top

Data collection: COLLECT (Nonius 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia,1999).

Figures top

	Fig. 1. The molecular structure of the title compound, (II), with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probabity level. H-atoms are represented by circles of arbitrary size.
	Fig. 2. The packing of (II), viewed down the a axis.
	Fig. 3. The structures of (I) and (II).

1-(1,5-Dimethylhexyl)-3a,5 b,12a,14a-tetramethyl- 2,3,3a,4,5,5a,5 b,11,12,13,14,14a-dodecahydro- 1H,12aH-cyclopentano[1,2]phenantreno[7,8-b]indole top

Crystal data top

C₃₅H₅₁N	F(000) = 1072
M_r = 485.77	D_x = 1.101 Mg m⁻³ D_m = not performed Mg m⁻³ D_m measured by not measured
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2013 reflections
a = 6.563 (2) Å	θ = 3.4–27.0°
b = 18.668 (4) Å	µ = 0.06 mm⁻¹
c = 23.930 (7) Å	T = 170 K
V = 2931.9 (14) Å³	Block, colourless
Z = 4	0.20 × 0.15 × 0.10 mm

Data collection top

Enraf-Nonius KappaCCD diffractometer	3234 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.071
Graphite monochromator	θ_max = 27.0°, θ_min = 3.4°
Detector resolution: 9 pixels mm^-1	h = 0→8
ϕ and ω scans	k = 0→23
16251 measured reflections	l = 0→30
3625 independent reflections

Refinement top

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0624P)² + 2.356P] where P = (F_o² + 2F_c²)/3
3625 reflections	(Δ/σ)_max < 0.001
330 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₃₅H₅₁N	V = 2931.9 (14) Å³
M_r = 485.77	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.563 (2) Å	µ = 0.06 mm⁻¹
b = 18.668 (4) Å	T = 170 K
c = 23.930 (7) Å	0.20 × 0.15 × 0.10 mm

Data collection top

Enraf-Nonius KappaCCD diffractometer	3234 reflections with I > 2σ(I)
16251 measured reflections	R_int = 0.071
3625 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	0 restraints
wR(F²) = 0.176	H-atom parameters constrained
S = 1.14	Δρ_max = 0.37 e Å⁻³
3625 reflections	Δρ_min = −0.26 e Å⁻³
330 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7821 (5)	0.11990 (16)	0.13819 (14)	0.0218 (7)
C1'	0.7970 (6)	0.05385 (18)	0.05148 (14)	0.0265 (8)
H1'	0.6820	0.0226	0.0608	0.032*
C1"	0.8396 (7)	0.0449 (2)	−0.01160 (15)	0.0355 (9)
H1"	0.9563	0.0753	−0.0213	0.043*
C2	0.7460 (5)	0.12964 (18)	0.07411 (14)	0.0235 (7)
C2'	0.9805 (6)	0.0304 (2)	0.08873 (16)	0.0345 (9)
H2'1	0.9611	−0.0183	0.1018	0.041*
H2'2	1.1063	0.0324	0.0675	0.041*
C2"	0.8968 (8)	−0.0333 (2)	−0.02462 (17)	0.0458 (11)
H2"1	0.9809	−0.0515	0.0056	0.055*
H2"2	0.7731	−0.0617	−0.0255	0.055*
C3	0.5296 (6)	0.15825 (19)	0.06657 (15)	0.0276 (8)
H3A	0.4328	0.1220	0.0783	0.033*
H3B	0.5058	0.1682	0.0273	0.033*
C3'	0.9900 (6)	0.08280 (19)	0.13891 (16)	0.0298 (8)
H3'1	1.0106	0.0571	0.1737	0.036*
H3'2	1.0992	0.1173	0.1342	0.036*
C3"	1.0112 (11)	−0.0440 (3)	−0.08002 (19)	0.0670 (16)
H3"1	0.9258	−0.0268	−0.1103	0.080*
H3"2	1.1334	−0.0147	−0.0795	0.080*
C4	0.4946 (6)	0.22715 (19)	0.10081 (15)	0.0295 (8)
H4A	0.5169	0.2677	0.0762	0.035*
H4B	0.3525	0.2283	0.1119	0.035*
C4"	1.0700 (14)	−0.1188 (4)	−0.0919 (3)	0.114 (3)
H4"1	0.9463	−0.1463	−0.0978	0.136*
H4"2	1.1358	−0.1380	−0.0588	0.136*
C4A	0.6224 (5)	0.23830 (17)	0.15256 (14)	0.0211 (7)
C4B	0.5965 (5)	0.31121 (17)	0.18229 (15)	0.0226 (7)
C5	0.3720 (5)	0.33502 (19)	0.18046 (16)	0.0270 (8)
H5A	0.2867	0.2956	0.1928	0.032*
H5B	0.3354	0.3460	0.1421	0.032*
C5"	1.2102 (14)	−0.1319 (6)	−0.1415 (3)	0.138 (4)
H5"	1.2279	−0.1840	−0.1418	0.165*
C6	0.3279 (5)	0.40146 (18)	0.21742 (16)	0.0286 (8)
H6A	0.4003	0.4428	0.2030	0.034*
H6B	0.1832	0.4120	0.2172	0.034*
C6"	1.1121 (13)	−0.1172 (4)	−0.1936 (3)	0.100 (2)
H6"1	0.9720	−0.1318	−0.1916	0.150*
H6"2	1.1793	−0.1432	−0.2229	0.150*
H6"3	1.1192	−0.0668	−0.2012	0.150*
C6A	0.3964 (5)	0.38538 (17)	0.27494 (16)	0.0263 (8)
N7	0.2790 (5)	0.37794 (17)	0.31774 (14)	0.0311 (7)
C7"	1.4140 (13)	−0.1051 (8)	−0.1367 (4)	0.207 (7)
H7"1	1.4693	−0.1185	−0.1010	0.310*
H7"2	1.4126	−0.0538	−0.1398	0.310*
H7"3	1.4966	−0.1249	−0.1659	0.310*
C7A	0.4075 (6)	0.3549 (2)	0.36270 (17)	0.0335 (9)
C8	0.3491 (7)	0.3450 (3)	0.41768 (19)	0.0468 (11)
H8	0.2149	0.3517	0.4290	0.056*
C8"	0.6588 (8)	0.0684 (2)	−0.04728 (17)	0.0475 (11)
H8"1	0.6824	0.0551	−0.0855	0.071*
H8"2	0.6430	0.1194	−0.0448	0.071*
H8"3	0.5372	0.0454	−0.0340	0.071*
C9	0.4993 (9)	0.3248 (3)	0.4551 (2)	0.0585 (14)
H9	0.4650	0.3174	0.4924	0.070*
C9"	0.8963 (6)	0.18492 (19)	0.04933 (16)	0.0328 (9)
H9"1	0.8606	0.1945	0.0111	0.049*
H9"2	1.0323	0.1661	0.0509	0.049*
H9"3	0.8894	0.2285	0.0705	0.049*
C10	0.6972 (9)	0.3154 (3)	0.4385 (2)	0.0584 (14)
H10	0.7943	0.3017	0.4648	0.070*
C10"	0.7275 (6)	0.36513 (18)	0.14958 (17)	0.0324 (9)
H10A	0.8691	0.3552	0.1559	0.049*
H10B	0.6969	0.4128	0.1620	0.049*
H10C	0.6982	0.3610	0.1104	0.049*
C11	0.7561 (7)	0.3259 (2)	0.38344 (18)	0.0472 (11)
H11	0.8911	0.3202	0.3725	0.057*
C11"	0.7645 (6)	0.4297 (2)	0.27791 (18)	0.0353 (9)
H11A	0.7225	0.4673	0.3027	0.053*
H11B	0.7605	0.4467	0.2401	0.053*
H11C	0.9009	0.4152	0.2870	0.053*
C11A	0.6074 (6)	0.3450 (2)	0.34519 (16)	0.0319 (9)
C11B	0.6194 (5)	0.36520 (18)	0.28420 (16)	0.0265 (8)
C11C	0.6612 (5)	0.30024 (17)	0.24441 (15)	0.0215 (7)
H11D	0.5745	0.2614	0.2584	0.026*
C12	0.8779 (5)	0.2720 (2)	0.24856 (17)	0.0301 (8)
H12A	0.9156	0.2670	0.2876	0.036*
H12B	0.9709	0.3059	0.2314	0.036*
C12"	0.6261 (6)	0.06843 (19)	0.16539 (15)	0.0312 (8)
H12C	0.6580	0.0626	0.2043	0.047*
H12D	0.6320	0.0227	0.1471	0.047*
H12E	0.4915	0.0880	0.1617	0.047*
C13	0.8958 (6)	0.19978 (18)	0.21951 (16)	0.0291 (8)
H13A	1.0366	0.1927	0.2085	0.035*
H13B	0.8617	0.1625	0.2462	0.035*
C13A	0.7632 (5)	0.19075 (17)	0.16878 (14)	0.0219 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0261 (17)	0.0158 (15)	0.0235 (18)	0.0017 (13)	−0.0030 (15)	0.0042 (13)
C1'	0.0300 (18)	0.0262 (17)	0.0232 (18)	−0.0008 (15)	0.0027 (15)	0.0029 (15)
C1"	0.049 (2)	0.035 (2)	0.0226 (19)	−0.0009 (18)	0.0076 (18)	0.0043 (16)
C2	0.0292 (18)	0.0235 (17)	0.0177 (17)	0.0007 (15)	0.0008 (15)	0.0046 (13)
C2'	0.040 (2)	0.0307 (19)	0.033 (2)	0.0076 (17)	0.0022 (19)	−0.0001 (17)
C2"	0.069 (3)	0.042 (2)	0.027 (2)	0.007 (2)	0.007 (2)	−0.0063 (18)
C3	0.0302 (19)	0.0292 (19)	0.0235 (18)	0.0036 (16)	−0.0053 (16)	−0.0018 (15)
C3'	0.0344 (19)	0.0257 (19)	0.0293 (19)	0.0106 (16)	−0.0040 (17)	−0.0010 (15)
C3"	0.100 (4)	0.069 (3)	0.032 (2)	0.004 (3)	0.015 (3)	0.001 (2)
C4	0.0250 (17)	0.034 (2)	0.030 (2)	0.0078 (16)	−0.0034 (17)	0.0008 (16)
C4"	0.146 (7)	0.141 (7)	0.054 (4)	0.076 (6)	0.011 (4)	−0.029 (4)
C4A	0.0159 (15)	0.0235 (16)	0.0238 (17)	−0.0012 (13)	0.0024 (14)	0.0057 (14)
C4B	0.0190 (15)	0.0188 (16)	0.0299 (19)	0.0026 (14)	0.0021 (15)	0.0042 (14)
C5	0.0238 (17)	0.0271 (18)	0.0302 (19)	0.0035 (15)	0.0000 (16)	0.0010 (15)
C5"	0.120 (7)	0.247 (11)	0.047 (4)	0.095 (8)	0.023 (4)	0.004 (5)
C6	0.0212 (17)	0.0212 (16)	0.043 (2)	0.0043 (14)	0.0004 (16)	−0.0004 (16)
C6"	0.110 (6)	0.131 (6)	0.060 (4)	0.014 (5)	0.008 (4)	−0.020 (4)
C6A	0.0221 (16)	0.0161 (15)	0.041 (2)	0.0011 (14)	−0.0001 (17)	−0.0086 (15)
N7	0.0189 (14)	0.0336 (17)	0.0410 (19)	0.0001 (13)	0.0028 (14)	−0.0116 (15)
C7"	0.063 (5)	0.42 (2)	0.136 (8)	0.021 (9)	−0.006 (5)	−0.174 (11)
C7A	0.036 (2)	0.0294 (19)	0.035 (2)	−0.0015 (17)	0.0002 (18)	−0.0100 (17)
C8	0.044 (2)	0.058 (3)	0.039 (2)	−0.001 (2)	0.005 (2)	−0.014 (2)
C8"	0.069 (3)	0.051 (3)	0.023 (2)	0.006 (2)	−0.001 (2)	0.0003 (19)
C9	0.078 (4)	0.066 (3)	0.032 (2)	−0.001 (3)	0.001 (3)	−0.010 (2)
C9"	0.039 (2)	0.0298 (19)	0.029 (2)	−0.0013 (18)	0.0099 (18)	0.0056 (16)
C10	0.065 (3)	0.072 (3)	0.038 (3)	0.016 (3)	−0.018 (2)	−0.010 (2)
C10"	0.0327 (19)	0.0241 (18)	0.040 (2)	0.0006 (16)	0.0047 (18)	0.0024 (16)
C11	0.043 (2)	0.060 (3)	0.039 (2)	0.014 (2)	−0.010 (2)	−0.014 (2)
C11"	0.0231 (18)	0.0301 (19)	0.053 (2)	−0.0044 (16)	−0.0004 (18)	−0.0173 (19)
C11A	0.0335 (19)	0.0299 (19)	0.032 (2)	−0.0002 (16)	−0.0063 (17)	−0.0128 (16)
C11B	0.0189 (16)	0.0249 (17)	0.036 (2)	0.0045 (14)	−0.0020 (16)	−0.0053 (16)
C11C	0.0180 (15)	0.0169 (15)	0.0296 (19)	0.0001 (13)	−0.0028 (14)	−0.0013 (14)
C12	0.0211 (17)	0.034 (2)	0.036 (2)	0.0048 (16)	−0.0061 (17)	−0.0050 (17)
C12"	0.046 (2)	0.0252 (18)	0.0226 (18)	−0.0024 (17)	0.0074 (18)	0.0029 (15)
C13	0.0267 (17)	0.0274 (18)	0.033 (2)	0.0084 (15)	−0.0051 (17)	0.0008 (16)
C13A	0.0175 (15)	0.0237 (16)	0.0244 (18)	−0.0019 (14)	0.0012 (14)	0.0029 (14)

Geometric parameters (Å, º) top

C1—C13A	1.517 (5)	C6—H6B	0.9700
C1—C3'	1.530 (5)	C6"—H6"1	0.9600
C1—C12"	1.548 (5)	C6"—H6"2	0.9600
C1—C2	1.562 (5)	C6"—H6"3	0.9600
C1'—C1"	1.544 (5)	C6A—N7	1.289 (5)
C1'—C2	1.552 (5)	C6A—C11B	1.527 (5)
C1'—C2'	1.561 (5)	N7—C7A	1.433 (5)
C1'—H1'	0.9800	C7"—H7"1	0.9600
C1"—C8"	1.526 (6)	C7"—H7"2	0.9600
C1"—C2"	1.540 (6)	C7"—H7"3	0.9600
C1"—H1"	0.9800	C7A—C8	1.383 (6)
C2—C3	1.528 (5)	C7A—C11A	1.389 (6)
C2—C9"	1.546 (5)	C8—C9	1.385 (7)
C2'—C3'	1.550 (5)	C8—H8	0.9300
C2'—H2'1	0.9700	C8"—H8"1	0.9600
C2'—H2'2	0.9700	C8"—H8"2	0.9600
C2"—C3"	1.537 (6)	C8"—H8"3	0.9600
C2"—H2"1	0.9700	C9—C10	1.370 (8)
C2"—H2"2	0.9700	C9—H9	0.9300
C3—C4	1.542 (5)	C9"—H9"1	0.9600
C3—H3A	0.9700	C9"—H9"2	0.9600
C3—H3B	0.9700	C9"—H9"3	0.9600
C3'—H3'1	0.9700	C10—C11	1.388 (7)
C3'—H3'2	0.9700	C10—H10	0.9300
C3"—C4"	1.478 (8)	C10"—H10A	0.9600
C3"—H3"1	0.9700	C10"—H10B	0.9600
C3"—H3"2	0.9700	C10"—H10C	0.9600
C4—C4A	1.510 (5)	C11—C11A	1.385 (6)
C4—H4A	0.9700	C11—H11	0.9300
C4—H4B	0.9700	C11"—C11B	1.543 (5)
C4"—C5"	1.522 (9)	C11"—H11A	0.9600
C4"—H4"1	0.9700	C11"—H11B	0.9600
C4"—H4"2	0.9700	C11"—H11C	0.9600
C4A—C13A	1.339 (4)	C11A—C11B	1.509 (5)
C4A—C4B	1.545 (5)	C11B—C11C	1.566 (5)
C4B—C10"	1.538 (5)	C11C—C12	1.520 (5)
C4B—C5	1.540 (5)	C11C—H11D	0.9800
C4B—C11C	1.559 (5)	C12—C13	1.522 (5)
C5—C6	1.550 (5)	C12—H12A	0.9700
C5—H5A	0.9700	C12—H12B	0.9700
C5—H5B	0.9700	C12"—H12C	0.9600
C5"—C6"	1.429 (10)	C12"—H12D	0.9600
C5"—C7"	1.433 (13)	C12"—H12E	0.9600
C5"—H5"	0.9800	C13—C13A	1.503 (5)
C6—C6A	1.479 (5)	C13—H13A	0.9700
C6—H6A	0.9700	C13—H13B	0.9700

C13A—C1—C3'	117.5 (3)	H6A—C6—H6B	108.4
C13A—C1—C12"	106.5 (3)	C5"—C6"—H6"1	109.5
C3'—C1—C12"	107.7 (3)	C5"—C6"—H6"2	109.5
C13A—C1—C2	111.1 (3)	H6"1—C6"—H6"2	109.5
C3'—C1—C2	101.5 (3)	C5"—C6"—H6"3	109.5
C12"—C1—C2	112.6 (3)	H6"1—C6"—H6"3	109.5
C1"—C1'—C2	118.6 (3)	H6"2—C6"—H6"3	109.5
C1"—C1'—C2'	112.8 (3)	N7—C6A—C6	125.4 (3)
C2—C1'—C2'	102.9 (3)	N7—C6A—C11B	115.5 (3)
C1"—C1'—H1'	107.3	C6—C6A—C11B	118.5 (3)
C2—C1'—H1'	107.3	C6A—N7—C7A	106.1 (3)
C2'—C1'—H1'	107.3	C5"—C7"—H7"1	109.5
C8"—C1"—C2"	110.4 (4)	C5"—C7"—H7"2	109.5
C8"—C1"—C1'	112.0 (3)	H7"1—C7"—H7"2	109.5
C2"—C1"—C1'	110.1 (3)	C5"—C7"—H7"3	109.5
C8"—C1"—H1"	108.1	H7"1—C7"—H7"3	109.5
C2"—C1"—H1"	108.1	H7"2—C7"—H7"3	109.5
C1'—C1"—H1"	108.1	C8—C7A—C11A	122.1 (4)
C3—C2—C9"	108.3 (3)	C8—C7A—N7	126.2 (4)
C3—C2—C1'	118.6 (3)	C11A—C7A—N7	111.6 (3)
C9"—C2—C1'	109.7 (3)	C7A—C8—C9	117.1 (4)
C3—C2—C1	107.3 (3)	C7A—C8—H8	121.5
C9"—C2—C1	110.9 (3)	C9—C8—H8	121.5
C1'—C2—C1	101.7 (3)	C1"—C8"—H8"1	109.5
C3'—C2'—C1'	107.2 (3)	C1"—C8"—H8"2	109.5
C3'—C2'—H2'1	110.3	H8"1—C8"—H8"2	109.5
C1'—C2'—H2'1	110.3	C1"—C8"—H8"3	109.5
C3'—C2'—H2'2	110.3	H8"1—C8"—H8"3	109.5
C1'—C2'—H2'2	110.3	H8"2—C8"—H8"3	109.5
H2'1—C2'—H2'2	108.5	C10—C9—C8	121.5 (5)
C3"—C2"—C1"	114.6 (4)	C10—C9—H9	119.3
C3"—C2"—H2"1	108.6	C8—C9—H9	119.3
C1"—C2"—H2"1	108.6	C2—C9"—H9"1	109.5
C3"—C2"—H2"2	108.6	C2—C9"—H9"2	109.5
C1"—C2"—H2"2	108.6	H9"1—C9"—H9"2	109.5
H2"1—C2"—H2"2	107.6	C2—C9"—H9"3	109.5
C2—C3—C4	111.5 (3)	H9"1—C9"—H9"3	109.5
C2—C3—H3A	109.3	H9"2—C9"—H9"3	109.5
C4—C3—H3A	109.3	C9—C10—C11	121.4 (5)
C2—C3—H3B	109.3	C9—C10—H10	119.3
C4—C3—H3B	109.3	C11—C10—H10	119.3
H3A—C3—H3B	108.0	C4B—C10"—H10A	109.5
C1—C3'—C2'	104.0 (3)	C4B—C10"—H10B	109.5
C1—C3'—H3'1	111.0	H10A—C10"—H10B	109.5
C2'—C3'—H3'1	111.0	C4B—C10"—H10C	109.5
C1—C3'—H3'2	111.0	H10A—C10"—H10C	109.5
C2'—C3'—H3'2	111.0	H10B—C10"—H10C	109.5
H3'1—C3'—H3'2	109.0	C11A—C11—C10	117.9 (4)
C4"—C3"—C2"	114.5 (5)	C11A—C11—H11	121.0
C4"—C3"—H3"1	108.6	C10—C11—H11	121.0
C2"—C3"—H3"1	108.6	C11B—C11"—H11A	109.5
C4"—C3"—H3"2	108.6	C11B—C11"—H11B	109.5
C2"—C3"—H3"2	108.6	H11A—C11"—H11B	109.5
H3"1—C3"—H3"2	107.6	C11B—C11"—H11C	109.5
C4A—C4—C3	117.9 (3)	H11A—C11"—H11C	109.5
C4A—C4—H4A	107.8	H11B—C11"—H11C	109.5
C3—C4—H4A	107.8	C11—C11A—C7A	120.0 (4)
C4A—C4—H4B	107.8	C11—C11A—C11B	131.8 (4)
C3—C4—H4B	107.8	C7A—C11A—C11B	107.9 (3)
H4A—C4—H4B	107.2	C11A—C11B—C6A	98.7 (3)
C3"—C4"—C5"	117.3 (7)	C11A—C11B—C11"	108.7 (3)
C3"—C4"—H4"1	108.0	C6A—C11B—C11"	112.6 (3)
C5"—C4"—H4"1	108.0	C11A—C11B—C11C	113.8 (3)
C3"—C4"—H4"2	108.0	C6A—C11B—C11C	105.7 (3)
C5"—C4"—H4"2	108.0	C11"—C11B—C11C	115.9 (3)
H4"1—C4"—H4"2	107.2	C12—C11C—C4B	111.2 (3)
C13A—C4A—C4	122.0 (3)	C12—C11C—C11B	113.1 (3)
C13A—C4A—C4B	121.8 (3)	C4B—C11C—C11B	115.5 (3)
C4—C4A—C4B	116.0 (3)	C12—C11C—H11D	105.3
C10"—C4B—C5	109.4 (3)	C4B—C11C—H11D	105.3
C10"—C4B—C4A	106.3 (3)	C11B—C11C—H11D	105.3
C5—C4B—C4A	110.3 (3)	C11C—C12—C13	110.4 (3)
C10"—C4B—C11C	114.8 (3)	C11C—C12—H12A	109.6
C5—C4B—C11C	109.0 (3)	C13—C12—H12A	109.6
C4A—C4B—C11C	107.1 (3)	C11C—C12—H12B	109.6
C4B—C5—C6	113.2 (3)	C13—C12—H12B	109.6
C4B—C5—H5A	108.9	H12A—C12—H12B	108.1
C6—C5—H5A	108.9	C1—C12"—H12C	109.5
C4B—C5—H5B	108.9	C1—C12"—H12D	109.5
C6—C5—H5B	108.9	H12C—C12"—H12D	109.5
H5A—C5—H5B	107.8	C1—C12"—H12E	109.5
C6"—C5"—C7"	115.1 (9)	H12C—C12"—H12E	109.5
C6"—C5"—C4"	112.2 (7)	H12D—C12"—H12E	109.5
C7"—C5"—C4"	116.4 (8)	C13A—C13—C12	115.1 (3)
C6"—C5"—H5"	103.7	C13A—C13—H13A	108.5
C7"—C5"—H5"	103.7	C12—C13—H13A	108.5
C4"—C5"—H5"	103.7	C13A—C13—H13B	108.5
C6A—C6—C5	108.2 (3)	C12—C13—H13B	108.5
C6A—C6—H6A	110.1	H13A—C13—H13B	107.5
C5—C6—H6A	110.1	C4A—C13A—C13	124.0 (3)
C6A—C6—H6B	110.1	C4A—C13A—C1	119.7 (3)
C5—C6—H6B	110.1	C13—C13A—C1	116.1 (3)

C2—C1'—C1"—C8"	−59.5 (5)	C6A—N7—C7A—C11A	−2.9 (4)
C2'—C1'—C1"—C8"	−179.8 (3)	C11A—C7A—C8—C9	0.1 (6)
C2—C1'—C1"—C2"	177.3 (4)	N7—C7A—C8—C9	−177.8 (4)
C2'—C1'—C1"—C2"	56.9 (5)	C7A—C8—C9—C10	0.4 (8)
C1"—C1'—C2—C3	79.7 (4)	C8—C9—C10—C11	0.1 (8)
C2'—C1'—C2—C3	−155.0 (3)	C9—C10—C11—C11A	−1.1 (8)
C1"—C1'—C2—C9"	−45.5 (4)	C10—C11—C11A—C7A	1.5 (6)
C2'—C1'—C2—C9"	79.9 (3)	C10—C11—C11A—C11B	175.2 (4)
C1"—C1'—C2—C1	−163.0 (3)	C8—C7A—C11A—C11	−1.1 (6)
C2'—C1'—C2—C1	−37.6 (3)	N7—C7A—C11A—C11	177.1 (3)
C13A—C1—C2—C3	−61.1 (3)	C8—C7A—C11A—C11B	−176.1 (4)
C3'—C1—C2—C3	173.2 (3)	N7—C7A—C11A—C11B	2.1 (4)
C12"—C1—C2—C3	58.3 (4)	C11—C11A—C11B—C6A	−174.7 (4)
C13A—C1—C2—C9"	57.1 (4)	C7A—C11A—C11B—C6A	−0.5 (4)
C3'—C1—C2—C9"	−68.6 (3)	C11—C11A—C11B—C11"	−57.1 (5)
C12"—C1—C2—C9"	176.5 (3)	C7A—C11A—C11B—C11"	117.1 (3)
C13A—C1—C2—C1'	173.7 (3)	C11—C11A—C11B—C11C	73.8 (5)
C3'—C1—C2—C1'	48.0 (3)	C7A—C11A—C11B—C11C	−112.0 (3)
C12"—C1—C2—C1'	−66.9 (3)	N7—C6A—C11B—C11A	−1.4 (4)
C1"—C1'—C2'—C3'	143.0 (3)	C6—C6A—C11B—C11A	−173.0 (3)
C2—C1'—C2'—C3'	14.0 (4)	N7—C6A—C11B—C11"	−116.0 (4)
C8"—C1"—C2"—C3"	75.7 (5)	C6—C6A—C11B—C11"	72.4 (4)
C1'—C1"—C2"—C3"	−160.1 (4)	N7—C6A—C11B—C11C	116.5 (3)
C9"—C2—C3—C4	−65.0 (4)	C6—C6A—C11B—C11C	−55.1 (4)
C1'—C2—C3—C4	169.2 (3)	C10"—C4B—C11C—C12	−60.6 (4)
C1—C2—C3—C4	54.9 (4)	C5—C4B—C11C—C12	176.3 (3)
C13A—C1—C3'—C2'	−160.1 (3)	C4A—C4B—C11C—C12	57.1 (3)
C12"—C1—C3'—C2'	79.7 (4)	C10"—C4B—C11C—C11B	70.0 (4)
C2—C1—C3'—C2'	−38.8 (3)	C5—C4B—C11C—C11B	−53.0 (4)
C1'—C2'—C3'—C1	15.6 (4)	C4A—C4B—C11C—C11B	−172.3 (3)
C1"—C2"—C3"—C4"	178.7 (6)	C11A—C11B—C11C—C12	−72.1 (4)
C2—C3—C4—C4A	−26.4 (4)	C6A—C11B—C11C—C12	−179.3 (3)
C2"—C3"—C4"—C5"	−171.2 (6)	C11"—C11B—C11C—C12	55.2 (4)
C3—C4—C4A—C13A	0.4 (5)	C11A—C11B—C11C—C4B	158.2 (3)
C3—C4—C4A—C4B	174.4 (3)	C6A—C11B—C11C—C4B	50.9 (4)
C13A—C4A—C4B—C10"	93.4 (4)	C11"—C11B—C11C—C4B	−74.6 (4)
C4—C4A—C4B—C10"	−80.7 (4)	C4B—C11C—C12—C13	−60.9 (4)
C13A—C4A—C4B—C5	−148.2 (3)	C11B—C11C—C12—C13	167.2 (3)
C4—C4A—C4B—C5	37.8 (4)	C11C—C12—C13—C13A	34.0 (4)
C13A—C4A—C4B—C11C	−29.7 (4)	C4—C4A—C13A—C13	179.3 (3)
C4—C4A—C4B—C11C	156.2 (3)	C4B—C4A—C13A—C13	5.6 (5)
C10"—C4B—C5—C6	−72.6 (4)	C4—C4A—C13A—C1	−6.4 (5)
C4A—C4B—C5—C6	170.9 (3)	C4B—C4A—C13A—C1	179.9 (3)
C11C—C4B—C5—C6	53.6 (4)	C12—C13—C13A—C4A	−6.9 (5)
C3"—C4"—C5"—C6"	−68.2 (12)	C12—C13—C13A—C1	178.5 (3)
C3"—C4"—C5"—C7"	67.3 (12)	C3'—C1—C13A—C4A	153.6 (3)
C4B—C5—C6—C6A	−55.2 (4)	C12"—C1—C13A—C4A	−85.6 (4)
C5—C6—C6A—N7	−112.6 (4)	C2—C1—C13A—C4A	37.4 (4)
C5—C6—C6A—C11B	58.1 (4)	C3'—C1—C13A—C13	−31.6 (4)
C6—C6A—N7—C7A	173.5 (3)	C12"—C1—C13A—C13	89.2 (4)
C11B—C6A—N7—C7A	2.6 (4)	C2—C1—C13A—C13	−147.8 (3)
C6A—N7—C7A—C8	175.1 (4)

Experimental details

Crystal data
Chemical formula	C₃₅H₅₁N
M_r	485.77
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	170
a, b, c (Å)	6.563 (2), 18.668 (4), 23.930 (7)
V (Å³)	2931.9 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.06
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Enraf-Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16251, 3625, 3234
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.176, 1.14
No. of reflections	3625
No. of parameters	330
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.26

Computer programs: COLLECT (Nonius 2000), SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK and DENZO (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), WinGX (Farrugia,1999).

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Format		BIBTeX
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		CIF
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1-(1,5-Dimethyl­hexyl)-3a,5b,12a,14a-tetra­methyl-2,3,3a,4,5,5a,5b,11,12,13,14,14a-dodeca­hydro-1H,12aH-cyclo­penta­[1,2]phenanthro[7,8-b]indole

Supporting information

Key indicators

checkCIF/PLATON results

1-(1,5-Dimethylhexyl)-3a,5b,12a,14a-tetramethyl-2,3,3a,4,5,5a,5b,11,12,13,14,14a-dodecahydro-1H,12aH-cyclopenta[1,2]phenanthro[7,8-b]indole