4-tert-Butyl-2-{[(E)-2,6-diisopropyl­phenyl­imino]meth­yl}-6-(1-phenyl­ethyl)phenol

Cui, J.; Zhang, M.; Zhu, J.; Cui, N.; Liu, B.

doi:10.1107/S1600536807051306

4-tert-Butyl-2-{[(E)-2,6-diisopropylphenylimino]methyl}-6-(1-phenylethyl)phenol

J. Cui, M. Zhang, J. Zhu, N. Cui and B. Liu

The title compound, C₃₁H₃₉NO, was prepared by the condensation of 5-tert-butyl-2-hydroxy-3-(1-phenylethyl)benzaldehyde with 2,6-diisopropylphenylamine in refluxing ethanol. The phenol ring and the phenylimino ring are approximately perpendicular, forming a dihedral angle of 81.5 (3)°. The phenyl ring makes a dihedral angle of 75.2 (2)° with the phenol ring and also makes a dihedral angle of 62.9 (3)° with the phenylimino ring. The molecular structure is stabilized by an intramolecular O—H

N hydrogen bond linking the phenol OH group and the phenylimino N atom. One of the isopropyl groups is disordered over two positions; the site occupancies are 0.55 and 0.45.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051306/cs2047sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051306/cs2047Isup2.hkl Contains datablock I

CCDC reference: 667418

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.038
wR factor = 0.105
Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.85
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.94 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.23 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C7'
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C5     -   C6     ...       1.39 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          7

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           25.01
           From the CIF: _reflns_number_total               2505
           Count of symmetry unique reflns         2503
           Completeness (_total/calc)            100.08%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         2
           Fraction of Friedel pairs measured     0.001
           Are heavy atom types Z>Si present         no
PLAT792_ALERT_1_G Check the Absolute Configuration of C24    = ...          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         41

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

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

Comment top

Late-metal catalysts bearing salicylaldiminato-type ligands play an important role in the catalytic oligomerization and polymerization of olefins (Ittel et al., 2000). Increasing the size of the imino substituent and the o-phenoxy substituent has a pronounced effect on the activity of the catalyst and the molecular weight of the polymer (Gibson et al., 2003). We have recently prepared a novel ligand, (I), and report its crystal structure here.

The molecular structure of (I) is shown in Fig. 1. In (I) the phenyl ring and the phenoxy ring form a dihedral angle of 75.18 (1)°, the phenylimino ring is nearly perpendicular to the phenoxy ring, with a dihedral angle of 81.51 (2)°. The dihedral angle between the phenyl and the phenylimino ring is 62.88 (1)°. Three C atoms of isopropyl attaching to the phenylimino ring are disordered in two locations with 55% and 45% probabilities. An intramolecular hydrogen bond is formed between the hydroxyl group and the N atom stabilizing the crystal structure.

Related literature top

For related literature, see: Gibson & Spitzmesser (2003); Ittel & Johnson (2000); Shriner et al. (1946).

Experimental top

2,6-Diisopropylaniline (3.94 g, 22.2 mmol) was added via syringe to a solution of 5-tert-Butyl-2-hydroxy-3-(1-phenyl-ethyl)-benzaldehyde (6.26 g, 22.2 mmol) in EtOH (100 ml). Formic acid (0.01 g, 0.22 mmol) was added and the solution refluxed for 20 h. The solution was dried over magnesium sulfate, filtered and the volatiles removed under reduced pressure. Extraction into pentane (5 ml) followed by cooling to 243 K afforded yellow crystals of (I) (yield 76%). Spectroscopic analysis: IR (KBr, ν, cm^-1): 3055.8, 3027.2, 2965.6, 2871.9, 1621.5, 1591.1, 1460.4, 1361.9, 1269.7, 1176.9, 855.7; ¹H NMR (CDCl₃, δ, p.p.m.): 1.188 (s, 12H), 1.305 (s, 9H), 1.692 (s, 3H), 3.021 (s, 2H), 4.756 (s, 1H), 7.182–7.369 (m, 10H), 8.287 (s, 1H), 13.146 (s, 1H)

Structure description top

For related literature, see: Gibson & Spitzmesser (2003); Ittel & Johnson (2000); Shriner et al. (1946).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top

Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level.

4-tert-Butyl-2-{[(E)-2,6-diisopropylphenylimino]methyl}-6-(1-phenylethyl)phenol top

Crystal data top

C₃₁H₃₉NO	D_x = 1.093 Mg m⁻³
M_r = 441.63	Melting point: 400 K
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
a = 25.273 (4) Å	Cell parameters from 3934 reflections
b = 9.5496 (18) Å	θ = 2.3–24.1°
c = 11.115 (2) Å	µ = 0.07 mm⁻¹
V = 2682.6 (8) Å³	T = 294 K
Z = 4	Block, yellow
F(000) = 960	0.24 × 0.20 × 0.16 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2505 independent reflections
Radiation source: fine-focus sealed tube	1964 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
φ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→30
T_min = 0.974, T_max = 0.990	k = −11→9
13332 measured reflections	l = −11→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0512P)² + 0.4436P] where P = (F_o² + 2F_c²)/3
2505 reflections	(Δ/σ)_max = 0.003
319 parameters	Δρ_max = 0.13 e Å⁻³
41 restraints	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₃₁H₃₉NO	V = 2682.6 (8) Å³
M_r = 441.63	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 25.273 (4) Å	µ = 0.07 mm⁻¹
b = 9.5496 (18) Å	T = 294 K
c = 11.115 (2) Å	0.24 × 0.20 × 0.16 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2505 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1964 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.990	R_int = 0.039
13332 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	41 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.13 e Å⁻³
2505 reflections	Δρ_min = −0.12 e Å⁻³
319 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.44217 (8)	0.0843 (2)	0.9096 (2)	0.0504 (5)
H1	0.4093 (15)	0.115 (4)	0.937 (4)	0.076*
N1	0.34993 (8)	0.2094 (3)	0.9030 (2)	0.0441 (6)
C1	0.29497 (10)	0.2202 (3)	0.9371 (3)	0.0420 (7)
C2	0.26067 (11)	0.1171 (3)	0.8930 (3)	0.0456 (7)
C3	0.20812 (12)	0.1214 (4)	0.9313 (3)	0.0571 (9)
H3A	0.1845	0.0538	0.9039	0.069*
C4	0.19064 (13)	0.2234 (4)	1.0087 (4)	0.0647 (10)
H4A	0.1555	0.2246	1.0331	0.078*
C5	0.22512 (13)	0.3240 (4)	1.0501 (3)	0.0597 (9)
H5A	0.2126	0.3936	1.1012	0.072*
C6	0.27828 (12)	0.3240 (3)	1.0173 (3)	0.0489 (8)
C7	0.31638 (13)	0.4301 (4)	1.0708 (3)	0.0585 (9)	0.55
H7A	0.3432	0.4506	1.0096	0.070*	0.55
C8	0.3442 (4)	0.3728 (10)	1.1771 (9)	0.093 (3)	0.55
H8A	0.3612	0.2864	1.1558	0.140*	0.55
H8B	0.3192	0.3560	1.2404	0.140*	0.55
H8C	0.3703	0.4387	1.2042	0.140*	0.55
C9	0.2903 (4)	0.5695 (8)	1.1056 (11)	0.094 (3)	0.55
H9A	0.2724	0.6078	1.0370	0.141*	0.55
H9B	0.3169	0.6340	1.1324	0.141*	0.55
H9C	0.2653	0.5539	1.1692	0.141*	0.55
C7'	0.31638 (13)	0.4301 (4)	1.0708 (3)	0.0585 (9)	0.45
H7'A	0.3517	0.4052	1.0413	0.070*	0.45
C8'	0.3184 (5)	0.4162 (15)	1.2099 (8)	0.101 (4)	0.45
H8'A	0.3426	0.4838	1.2420	0.152*	0.45
H8'B	0.3299	0.3237	1.2311	0.152*	0.45
H8'C	0.2837	0.4325	1.2426	0.152*	0.45
C9'	0.3053 (5)	0.5723 (10)	1.0256 (14)	0.101 (4)	0.45
H9'A	0.3053	0.5715	0.9392	0.152*	0.45
H9'B	0.3320	0.6356	1.0540	0.152*	0.45
H9'C	0.2712	0.6023	1.0540	0.152*	0.45
C10	0.27988 (12)	0.0008 (3)	0.8111 (3)	0.0538 (8)
H10A	0.3106	0.0365	0.7670	0.065*
C11	0.23939 (16)	−0.0449 (5)	0.7194 (4)	0.0823 (13)
H11A	0.2287	0.0343	0.6720	0.124*
H11B	0.2091	−0.0831	0.7599	0.124*
H11C	0.2546	−0.1149	0.6679	0.124*
C12	0.29860 (19)	−0.1216 (4)	0.8871 (4)	0.0941 (14)
H12A	0.3245	−0.0896	0.9440	0.141*
H12B	0.3141	−0.1915	0.8360	0.141*
H12C	0.2690	−0.1613	0.9293	0.141*
C13	0.36706 (10)	0.2802 (3)	0.8142 (3)	0.0403 (6)
H13A	0.3447	0.3457	0.7788	0.048*
C14	0.42028 (10)	0.2630 (3)	0.7657 (2)	0.0344 (6)
C15	0.43582 (11)	0.3420 (3)	0.6666 (3)	0.0390 (6)
H15A	0.4126	0.4092	0.6367	0.047*
C16	0.48415 (11)	0.3248 (3)	0.6105 (3)	0.0394 (7)
C17	0.51775 (11)	0.2242 (3)	0.6607 (3)	0.0415 (7)
H17A	0.5506	0.2102	0.6251	0.050*
C18	0.50481 (10)	0.1442 (3)	0.7606 (3)	0.0378 (6)
C19	0.45548 (10)	0.1634 (3)	0.8132 (2)	0.0351 (6)
C20	0.50008 (12)	0.4134 (3)	0.5021 (3)	0.0501 (8)
C21	0.45576 (16)	0.4140 (5)	0.4080 (4)	0.0873 (13)
H21A	0.4237	0.4480	0.4440	0.131*
H21B	0.4502	0.3205	0.3788	0.131*
H21C	0.4655	0.4738	0.3423	0.131*
C22	0.50891 (19)	0.5640 (4)	0.5434 (4)	0.0891 (14)
H22A	0.4775	0.5980	0.5823	0.134*
H22B	0.5168	0.6218	0.4751	0.134*
H22C	0.5380	0.5669	0.5990	0.134*
C23	0.55002 (16)	0.3593 (5)	0.4403 (4)	0.0898 (14)
H23A	0.5787	0.3581	0.4969	0.135*
H23B	0.5589	0.4197	0.3742	0.135*
H23C	0.5439	0.2662	0.4109	0.135*
C24	0.54360 (11)	0.0404 (3)	0.8163 (3)	0.0484 (7)
H24A	0.5223	−0.0311	0.8570	0.058*
C25	0.57752 (15)	−0.0359 (4)	0.7233 (4)	0.0720 (11)
H25A	0.6009	−0.0999	0.7635	0.108*
H25B	0.5980	0.0310	0.6787	0.108*
H25C	0.5550	−0.0869	0.6692	0.108*
C26	0.57654 (11)	0.1120 (3)	0.9126 (3)	0.0453 (7)
C27	0.61133 (12)	0.2191 (4)	0.8845 (3)	0.0595 (9)
H27A	0.6149	0.2469	0.8047	0.071*
C28	0.64090 (15)	0.2858 (4)	0.9719 (4)	0.0753 (12)
H28A	0.6639	0.3579	0.9511	0.090*
C29	0.63612 (18)	0.2449 (5)	1.0891 (4)	0.0883 (14)
H29A	0.6560	0.2889	1.1485	0.106*
C30	0.60198 (18)	0.1388 (5)	1.1194 (4)	0.0839 (12)
H30A	0.5987	0.1112	1.1993	0.101*
C31	0.57252 (13)	0.0728 (4)	1.0313 (3)	0.0631 (9)
H31A	0.5496	0.0007	1.0526	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0451 (11)	0.0618 (13)	0.0441 (12)	0.0068 (10)	0.0068 (10)	0.0183 (11)
N1	0.0306 (11)	0.0593 (15)	0.0424 (14)	−0.0006 (11)	0.0055 (11)	0.0033 (13)
C1	0.0327 (14)	0.0546 (17)	0.0388 (16)	0.0000 (13)	0.0058 (12)	0.0033 (15)
C2	0.0379 (16)	0.0617 (18)	0.0373 (16)	−0.0015 (13)	0.0073 (13)	0.0017 (15)
C3	0.0375 (16)	0.079 (2)	0.055 (2)	−0.0110 (15)	0.0061 (16)	−0.0081 (19)
C4	0.0375 (17)	0.083 (2)	0.073 (2)	−0.0009 (17)	0.0173 (18)	−0.004 (2)
C5	0.0496 (19)	0.068 (2)	0.062 (2)	0.0047 (16)	0.0191 (18)	−0.0052 (19)
C6	0.0430 (17)	0.0568 (19)	0.0468 (18)	−0.0007 (14)	0.0076 (15)	−0.0001 (16)
C7	0.054 (2)	0.058 (2)	0.063 (2)	−0.0073 (16)	0.0126 (17)	−0.0091 (18)
C8	0.088 (6)	0.087 (5)	0.105 (6)	−0.007 (4)	−0.039 (5)	0.009 (5)
C9	0.103 (6)	0.062 (4)	0.117 (7)	0.002 (4)	−0.016 (5)	−0.004 (5)
C7'	0.054 (2)	0.058 (2)	0.063 (2)	−0.0073 (16)	0.0126 (17)	−0.0091 (18)
C8'	0.097 (7)	0.107 (8)	0.100 (7)	−0.017 (6)	−0.023 (6)	−0.001 (6)
C9'	0.104 (7)	0.076 (6)	0.123 (8)	−0.008 (5)	0.000 (7)	0.017 (6)
C10	0.0483 (17)	0.071 (2)	0.0425 (17)	−0.0054 (15)	0.0089 (16)	−0.0042 (18)
C11	0.078 (3)	0.102 (3)	0.067 (2)	−0.020 (2)	0.001 (2)	−0.028 (2)
C12	0.129 (4)	0.083 (3)	0.070 (3)	0.034 (3)	0.023 (3)	−0.001 (3)
C13	0.0318 (14)	0.0524 (16)	0.0368 (15)	0.0004 (12)	−0.0002 (13)	0.0025 (15)
C14	0.0303 (14)	0.0432 (14)	0.0298 (13)	−0.0047 (11)	−0.0031 (11)	0.0008 (13)
C15	0.0345 (15)	0.0472 (15)	0.0351 (15)	0.0012 (12)	−0.0038 (13)	0.0037 (14)
C16	0.0347 (15)	0.0487 (16)	0.0346 (15)	−0.0063 (12)	−0.0004 (13)	0.0021 (13)
C17	0.0293 (14)	0.0566 (17)	0.0385 (15)	−0.0018 (12)	0.0038 (12)	0.0012 (15)
C18	0.0327 (15)	0.0434 (15)	0.0371 (16)	0.0001 (11)	−0.0028 (12)	0.0002 (14)
C19	0.0337 (14)	0.0413 (14)	0.0303 (14)	−0.0061 (11)	−0.0007 (12)	0.0023 (13)
C20	0.0473 (18)	0.062 (2)	0.0412 (18)	−0.0058 (14)	0.0078 (14)	0.0118 (16)
C21	0.081 (3)	0.131 (4)	0.051 (2)	−0.006 (2)	−0.005 (2)	0.026 (3)
C22	0.116 (4)	0.070 (3)	0.081 (3)	−0.027 (2)	0.019 (3)	0.021 (2)
C23	0.073 (3)	0.116 (3)	0.081 (3)	0.012 (2)	0.038 (2)	0.038 (3)
C24	0.0387 (16)	0.0498 (17)	0.0567 (19)	0.0062 (13)	0.0012 (15)	0.0023 (16)
C25	0.067 (2)	0.077 (3)	0.072 (2)	0.024 (2)	−0.003 (2)	−0.007 (2)
C26	0.0308 (14)	0.0571 (18)	0.0479 (18)	0.0103 (13)	0.0022 (14)	0.0090 (16)
C27	0.0482 (19)	0.073 (2)	0.057 (2)	0.0023 (17)	−0.0059 (17)	0.0125 (19)
C28	0.055 (2)	0.080 (3)	0.091 (3)	−0.0040 (18)	−0.025 (2)	0.013 (2)
C29	0.082 (3)	0.099 (3)	0.084 (3)	0.009 (3)	−0.044 (3)	0.000 (3)
C30	0.089 (3)	0.106 (3)	0.057 (2)	0.011 (3)	−0.021 (2)	0.018 (2)
C31	0.057 (2)	0.079 (2)	0.054 (2)	0.0035 (17)	−0.0029 (18)	0.0169 (19)

Geometric parameters (Å, º) top

O1—C19	1.354 (3)	C13—H13A	0.9300
O1—H1	0.93 (4)	C14—C15	1.392 (4)
N1—C13	1.272 (4)	C14—C19	1.405 (4)
N1—C1	1.443 (3)	C15—C16	1.381 (4)
C1—C6	1.398 (4)	C15—H15A	0.9300
C1—C2	1.400 (4)	C16—C17	1.398 (4)
C2—C3	1.395 (4)	C16—C20	1.526 (4)
C2—C10	1.516 (4)	C17—C18	1.387 (4)
C3—C4	1.372 (5)	C17—H17A	0.9300
C3—H3A	0.9300	C18—C19	1.389 (4)
C4—C5	1.376 (5)	C18—C24	1.525 (4)
C4—H4A	0.9300	C20—C22	1.527 (5)
C5—C6	1.392 (4)	C20—C23	1.527 (5)
C5—H5A	0.9300	C20—C21	1.532 (5)
C6—C7	1.520 (5)	C21—H21A	0.9600
C7—C8	1.480 (7)	C21—H21B	0.9600
C7—C9	1.535 (7)	C21—H21C	0.9600
C7—H7A	0.9800	C22—H22A	0.9600
C8—H8A	0.9600	C22—H22B	0.9600
C8—H8B	0.9600	C22—H22C	0.9600
C8—H8C	0.9600	C23—H23A	0.9600
C9—H9A	0.9600	C23—H23B	0.9600
C9—H9B	0.9600	C23—H23C	0.9600
C9—H9C	0.9600	C24—C26	1.519 (5)
C8'—H8'A	0.9600	C24—C25	1.528 (5)
C8'—H8'B	0.9600	C24—H24A	0.9800
C8'—H8'C	0.9600	C25—H25A	0.9600
C9'—H9'A	0.9600	C25—H25B	0.9600
C9'—H9'B	0.9600	C25—H25C	0.9600
C9'—H9'C	0.9600	C26—C31	1.375 (5)
C10—C11	1.509 (5)	C26—C27	1.385 (4)
C10—C12	1.517 (5)	C27—C28	1.381 (5)
C10—H10A	0.9800	C27—H27A	0.9300
C11—H11A	0.9600	C28—C29	1.366 (6)
C11—H11B	0.9600	C28—H28A	0.9300
C11—H11C	0.9600	C29—C30	1.373 (6)
C12—H12A	0.9600	C29—H29A	0.9300
C12—H12B	0.9600	C30—C31	1.383 (6)
C12—H12C	0.9600	C30—H30A	0.9300
C13—C14	1.458 (4)	C31—H31A	0.9300

C19—O1—H1	108 (2)	C16—C15—H15A	118.6
C13—N1—C1	119.5 (2)	C14—C15—H15A	118.6
C6—C1—C2	122.3 (3)	C15—C16—C17	116.0 (3)
C6—C1—N1	120.6 (3)	C15—C16—C20	121.6 (3)
C2—C1—N1	117.0 (3)	C17—C16—C20	122.4 (2)
C3—C2—C1	117.5 (3)	C18—C17—C16	123.7 (3)
C3—C2—C10	120.6 (3)	C18—C17—H17A	118.1
C1—C2—C10	121.8 (2)	C16—C17—H17A	118.1
C4—C3—C2	121.2 (3)	C17—C18—C19	118.4 (2)
C4—C3—H3A	119.4	C17—C18—C24	122.1 (3)
C2—C3—H3A	119.4	C19—C18—C24	119.5 (3)
C3—C4—C5	120.1 (3)	O1—C19—C18	118.8 (2)
C3—C4—H4A	120.0	O1—C19—C14	121.2 (2)
C5—C4—H4A	120.0	C18—C19—C14	120.0 (2)
C4—C5—C6	121.6 (3)	C16—C20—C22	108.8 (3)
C4—C5—H5A	119.2	C16—C20—C23	112.7 (3)
C6—C5—H5A	119.2	C22—C20—C23	109.5 (3)
C5—C6—C1	117.3 (3)	C16—C20—C21	110.4 (3)
C5—C6—C7	120.6 (3)	C22—C20—C21	108.0 (3)
C1—C6—C7	122.1 (3)	C23—C20—C21	107.4 (3)
C8—C7—C6	111.5 (5)	C20—C21—H21A	109.5
C8—C7—C9	108.9 (7)	C20—C21—H21B	109.5
C6—C7—C9	113.9 (4)	H21A—C21—H21B	109.5
C8—C7—H7A	107.4	C20—C21—H21C	109.5
C6—C7—H7A	107.4	H21A—C21—H21C	109.5
C9—C7—H7A	107.4	H21B—C21—H21C	109.5
C7—C8—H8A	109.5	C20—C22—H22A	109.5
C7—C8—H8B	109.5	C20—C22—H22B	109.5
H8A—C8—H8B	109.5	H22A—C22—H22B	109.5
C7—C8—H8C	109.5	C20—C22—H22C	109.5
H8A—C8—H8C	109.5	H22A—C22—H22C	109.5
H8B—C8—H8C	109.5	H22B—C22—H22C	109.5
C7—C9—H9A	109.5	C20—C23—H23A	109.5
C7—C9—H9B	109.5	C20—C23—H23B	109.5
H9A—C9—H9B	109.5	H23A—C23—H23B	109.5
C7—C9—H9C	109.5	C20—C23—H23C	109.5
H9A—C9—H9C	109.5	H23A—C23—H23C	109.5
H9B—C9—H9C	109.5	H23B—C23—H23C	109.5
H8'A—C8'—H8'B	109.5	C26—C24—C18	110.2 (2)
H8'A—C8'—H8'C	109.5	C26—C24—C25	112.6 (3)
H8'B—C8'—H8'C	109.5	C18—C24—C25	113.4 (3)
H9'A—C9'—H9'B	109.5	C26—C24—H24A	106.7
H9'A—C9'—H9'C	109.5	C18—C24—H24A	106.7
H9'B—C9'—H9'C	109.5	C25—C24—H24A	106.7
C11—C10—C2	113.6 (3)	C24—C25—H25A	109.5
C11—C10—C12	111.4 (3)	C24—C25—H25B	109.5
C2—C10—C12	109.3 (3)	H25A—C25—H25B	109.5
C11—C10—H10A	107.4	C24—C25—H25C	109.5
C2—C10—H10A	107.4	H25A—C25—H25C	109.5
C12—C10—H10A	107.4	H25B—C25—H25C	109.5
C10—C11—H11A	109.5	C31—C26—C27	117.7 (3)
C10—C11—H11B	109.5	C31—C26—C24	120.9 (3)
H11A—C11—H11B	109.5	C27—C26—C24	121.4 (3)
C10—C11—H11C	109.5	C28—C27—C26	121.7 (3)
H11A—C11—H11C	109.5	C28—C27—H27A	119.1
H11B—C11—H11C	109.5	C26—C27—H27A	119.1
C10—C12—H12A	109.5	C29—C28—C27	119.4 (4)
C10—C12—H12B	109.5	C29—C28—H28A	120.3
H12A—C12—H12B	109.5	C27—C28—H28A	120.3
C10—C12—H12C	109.5	C28—C29—C30	120.0 (4)
H12A—C12—H12C	109.5	C28—C29—H29A	120.0
H12B—C12—H12C	109.5	C30—C29—H29A	120.0
N1—C13—C14	122.7 (3)	C29—C30—C31	120.1 (4)
N1—C13—H13A	118.6	C29—C30—H30A	120.0
C14—C13—H13A	118.6	C31—C30—H30A	120.0
C15—C14—C19	119.0 (2)	C26—C31—C30	121.1 (4)
C15—C14—C13	119.5 (2)	C26—C31—H31A	119.5
C19—C14—C13	121.4 (2)	C30—C31—H31A	119.5
C16—C15—C14	122.9 (3)

C13—N1—C1—C6	−87.7 (3)	C16—C17—C18—C19	0.9 (4)
C13—N1—C1—C2	96.7 (3)	C16—C17—C18—C24	−177.1 (3)
C6—C1—C2—C3	0.5 (4)	C17—C18—C19—O1	179.0 (2)
N1—C1—C2—C3	176.1 (3)	C24—C18—C19—O1	−3.0 (4)
C6—C1—C2—C10	−176.7 (3)	C17—C18—C19—C14	−0.7 (4)
N1—C1—C2—C10	−1.2 (4)	C24—C18—C19—C14	177.3 (3)
C1—C2—C3—C4	0.4 (5)	C15—C14—C19—O1	179.9 (2)
C10—C2—C3—C4	177.8 (3)	C13—C14—C19—O1	−3.3 (4)
C2—C3—C4—C5	−0.1 (6)	C15—C14—C19—C18	−0.4 (4)
C3—C4—C5—C6	−1.3 (6)	C13—C14—C19—C18	176.4 (3)
C4—C5—C6—C1	2.2 (5)	C15—C16—C20—C22	69.1 (4)
C4—C5—C6—C7	−175.8 (3)	C17—C16—C20—C22	−109.4 (3)
C2—C1—C6—C5	−1.8 (4)	C15—C16—C20—C23	−169.3 (3)
N1—C1—C6—C5	−177.2 (3)	C17—C16—C20—C23	12.2 (4)
C2—C1—C6—C7	176.2 (3)	C15—C16—C20—C21	−49.2 (4)
N1—C1—C6—C7	0.8 (4)	C17—C16—C20—C21	132.3 (3)
C5—C6—C7—C8	94.5 (6)	C17—C18—C24—C26	90.3 (3)
C1—C6—C7—C8	−83.4 (6)	C19—C18—C24—C26	−87.6 (3)
C5—C6—C7—C9	−29.2 (7)	C17—C18—C24—C25	−37.0 (4)
C1—C6—C7—C9	152.9 (6)	C19—C18—C24—C25	145.1 (3)
C3—C2—C10—C11	36.4 (4)	C18—C24—C26—C31	115.0 (3)
C1—C2—C10—C11	−146.4 (3)	C25—C24—C26—C31	−117.3 (4)
C3—C2—C10—C12	−88.6 (4)	C18—C24—C26—C27	−64.6 (4)
C1—C2—C10—C12	88.6 (4)	C25—C24—C26—C27	63.1 (4)
C1—N1—C13—C14	−172.8 (3)	C31—C26—C27—C28	−0.5 (5)
N1—C13—C14—C15	178.5 (3)	C24—C26—C27—C28	179.2 (3)
N1—C13—C14—C19	1.7 (4)	C26—C27—C28—C29	0.4 (6)
C19—C14—C15—C16	1.4 (4)	C27—C28—C29—C30	−0.3 (7)
C13—C14—C15—C16	−175.5 (3)	C28—C29—C30—C31	0.2 (7)
C14—C15—C16—C17	−1.2 (4)	C27—C26—C31—C30	0.4 (5)
C14—C15—C16—C20	−179.8 (3)	C24—C26—C31—C30	−179.2 (3)
C15—C16—C17—C18	0.1 (4)	C29—C30—C31—C26	−0.3 (6)
C20—C16—C17—C18	178.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.93 (4)	1.79 (4)	2.620 (3)	147 (3)

Experimental details

Crystal data
Chemical formula	C₃₁H₃₉NO
M_r	441.63
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	294
a, b, c (Å)	25.273 (4), 9.5496 (18), 11.115 (2)
V (Å³)	2682.6 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.24 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.974, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	13332, 2505, 1964
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.06
No. of reflections	2505
No. of parameters	319
No. of restraints	41
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.12

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).