1,3-Bis(4-tert-butyl­phen­yl)-4-nitro­butan-1-one

Ren, D.-Y.; Shi, L.; Zhang, Q.; Xu, Y.; Zhu, H.-J.

doi:10.1107/S1600536811018277

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1465

doi:10.1107/S1600536811018277

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1,3-Bis(4-tert-butylphenyl)-4-nitrobutan-1-one

Dong-Yin Ren,^a Lu Shi,^a Qin Zhang,^a Yi Xu ^a and Hong-Jun Zhu ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: zhuhj@njut.edu.cn

(Received 25 March 2011; accepted 13 May 2011; online 20 May 2011)

In the crystal structure of the title compound, C₂₄H₃₁NO₃, molecules are connected via C—H⋯O intermolecular hydrogen bonds, forming dimers. The benzene rings are oriented at a dihedral angle of 29.8 (1)°.

Related literature

For applications of the title compound, see: Gorman et al. (2004 ). For a related structure, see: Hall et al. (2005 ). For the synthesis of the title compound, see: Liang et al. (2006 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₄H₃₁NO₃
M_r = 381.50
Orthorhombic, P n a 2₁
a = 20.440 (4) Å
b = 17.500 (4) Å
c = 6.1630 (12) Å
V = 2204.5 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.985, T_max = 0.993
8662 measured reflections
2247 independent reflections
1527 reflections with I > 2σ(I)
R_int = 0.096
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.181
S = 1.00
2247 reflections
247 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1ⁱ	0.97	2.52	3.072 (5)	116
Symmetry code: (i) $[-x+1, -y+1, z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf-Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018277/bq2291sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018277/bq2291Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811018277/bq2291Isup3.cml

checkCIF report

Comment top

The tittle compound, 1,3-bis(4-tert-butylphenyl)-4-nitrobutan-1-one is an important intermediate (Gorman et al., 2004) for the synthesis of 2,4-bis(4-tert-butylphenyl)-4-oxobutanal, which can be used to synthesis 2,4-bis(4-tert-butylphenyl)-1H-pyrrole(Hall et al., 2005). We report here the crystal structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1. The dihedral angle between the rings (C5—C10) and (C15—C20) is 29.8 (1)°. The bond lengths and angles are within normal ranges (Allen et al., 1987).

The molecules of (I) were connected together via C—H···O intermolecular hydrogen bonds to form molecular dimers (Table 1. and Fig. 2.).

Related literature top

For applications of the title compound, see: Gorman et al. (2004). For a related structure, see: Hall et al. (2005). For the synthesis of the title compound, see: Liang et al. (2006). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound, (I) was prepared by the method of Michael reaction reported in literature (Liang et al., 2006). The crystals were obtained by dissolving (I) (0.2 g, 0.52 mmol) in ethanol (25 ml) and evaporating the solvent slowly at room temperature for about 5 d.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1985); cell refinement: CAD-4 Software (Enraf-Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

1,3-Bis(4-tert-butylphenyl)-4-nitrobutan-1-one top

Crystal data top

C₂₄H₃₁NO₃	F(000) = 824
M_r = 381.50	D_x = 1.149 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 25 reflections
a = 20.440 (4) Å	θ = 9–13°
b = 17.500 (4) Å	µ = 0.08 mm⁻¹
c = 6.1630 (12) Å	T = 293 K
V = 2204.5 (8) Å³	Block, colourless
Z = 4	0.20 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1527 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.096
Graphite monochromator	θ_max = 25.4°, θ_min = 1.5°
ω/2θ scans	h = −24→24
Absorption correction: ψ scan (North et al., 1968)	k = −21→21
T_min = 0.985, T_max = 0.993	l = −7→0
8662 measured reflections	3 standard reflections every 200 reflections
2247 independent reflections	intensity decay: 1%

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.181	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1P)² + 0.3P] where P = (F_o² + 2F_c²)/3
2247 reflections	(Δ/σ)_max < 0.001
247 parameters	Δρ_max = 0.35 e Å⁻³
1 restraint	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₄H₃₁NO₃	V = 2204.5 (8) Å³
M_r = 381.50	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 20.440 (4) Å	µ = 0.08 mm⁻¹
b = 17.500 (4) Å	T = 293 K
c = 6.1630 (12) Å	0.20 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1527 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.096
T_min = 0.985, T_max = 0.993	3 standard reflections every 200 reflections
8662 measured reflections	intensity decay: 1%
2247 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	1 restraint
wR(F²) = 0.181	H-atom parameters constrained
S = 1.00	Δρ_max = 0.35 e Å⁻³
2247 reflections	Δρ_min = −0.32 e Å⁻³
247 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
N	0.6807 (2)	0.5602 (3)	0.0686 (7)	0.0600 (11)
O1	0.50125 (15)	0.54161 (17)	0.2287 (6)	0.0631 (10)
C1	0.4134 (3)	0.9145 (3)	0.5244 (13)	0.0861 (15)
H1A	0.3856	0.8949	0.4118	0.129*
H1B	0.4564	0.9235	0.4669	0.129*
H1C	0.3957	0.9615	0.5788	0.129*
O2	0.73656 (19)	0.5582 (3)	0.1435 (8)	0.0888 (14)
C2	0.4638 (4)	0.8985 (4)	0.8758 (18)	0.128 (4)
H2A	0.4453	0.9465	0.9193	0.192*
H2B	0.5063	0.9070	0.8136	0.192*
H2C	0.4679	0.8658	1.0001	0.192*
O3	0.6580 (2)	0.6145 (2)	−0.0204 (9)	0.0976 (16)
C3	0.3532 (4)	0.8505 (4)	0.813 (2)	0.141 (4)
H3A	0.3221	0.8277	0.7162	0.211*
H3B	0.3377	0.8999	0.8576	0.211*
H3C	0.3585	0.8185	0.9385	0.211*
C4	0.4174 (3)	0.8589 (3)	0.7002 (13)	0.0861 (15)
C5	0.4448 (2)	0.7832 (3)	0.6253 (9)	0.0524 (12)
C6	0.4948 (2)	0.7455 (3)	0.7359 (9)	0.0549 (12)
H6A	0.5103	0.7660	0.8652	0.066*
C7	0.5216 (2)	0.6792 (2)	0.6595 (8)	0.0505 (12)
H7A	0.5552	0.6560	0.7369	0.061*
C8	0.49945 (19)	0.6457 (2)	0.4682 (8)	0.0405 (10)
C9	0.4479 (2)	0.6811 (3)	0.3611 (10)	0.0569 (13)
H9A	0.4306	0.6594	0.2358	0.068*
C10	0.4224 (3)	0.7479 (3)	0.4400 (11)	0.0654 (15)
H10A	0.3882	0.7707	0.3644	0.078*
C11	0.5300 (2)	0.5762 (2)	0.3703 (8)	0.0416 (10)
C12	0.5950 (2)	0.5512 (2)	0.4511 (8)	0.0418 (10)
H12A	0.5919	0.5420	0.6059	0.050*
H12B	0.6260	0.5925	0.4295	0.050*
C13	0.6218 (2)	0.4789 (2)	0.3414 (8)	0.0427 (11)
H13A	0.5858	0.4420	0.3412	0.051*
C14	0.6395 (2)	0.4918 (3)	0.1035 (9)	0.0530 (12)
H14A	0.6626	0.4472	0.0497	0.064*
H14B	0.5996	0.4971	0.0199	0.064*
C15	0.6768 (2)	0.4417 (2)	0.4692 (8)	0.0435 (10)
C16	0.7202 (2)	0.4823 (2)	0.5969 (9)	0.0453 (11)
H16A	0.7172	0.5352	0.6026	0.054*
C17	0.76808 (19)	0.4452 (2)	0.7167 (9)	0.0460 (11)
H17A	0.7970	0.4742	0.7989	0.055*
C18	0.7743 (2)	0.3668 (2)	0.7183 (9)	0.0466 (11)
C19	0.7315 (2)	0.3266 (2)	0.5847 (11)	0.0605 (14)
H19A	0.7358	0.2739	0.5732	0.073*
C20	0.6833 (2)	0.3630 (2)	0.4697 (10)	0.0538 (12)
H20A	0.6540	0.3338	0.3893	0.065*
C21	0.8267 (3)	0.3263 (3)	0.8525 (11)	0.0643 (14)
C22	0.8825 (3)	0.3032 (5)	0.6997 (15)	0.119 (3)
H22A	0.9157	0.2770	0.7807	0.179*
H22B	0.9008	0.3481	0.6342	0.179*
H22C	0.8658	0.2700	0.5886	0.179*
C23	0.8533 (4)	0.3767 (4)	1.0330 (14)	0.103 (3)
H23A	0.8183	0.3911	1.1285	0.154*
H23B	0.8725	0.4218	0.9713	0.154*
H23C	0.8859	0.3491	1.1133	0.154*
C24	0.7971 (3)	0.2562 (4)	0.9646 (15)	0.099 (2)
H24A	0.7630	0.2722	1.0617	0.148*
H24B	0.8305	0.2300	1.0450	0.148*
H24C	0.7791	0.2224	0.8572	0.148*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.069 (3)	0.076 (3)	0.035 (2)	−0.006 (2)	0.010 (2)	0.002 (2)
O1	0.0523 (18)	0.0704 (19)	0.066 (2)	0.0060 (16)	−0.0210 (19)	−0.028 (2)
C1	0.108 (3)	0.061 (2)	0.089 (4)	0.013 (3)	0.026 (3)	0.002 (2)
O2	0.066 (2)	0.131 (3)	0.069 (3)	−0.036 (2)	0.002 (2)	0.011 (3)
C2	0.106 (5)	0.105 (5)	0.174 (10)	0.027 (4)	−0.021 (7)	−0.067 (7)
O3	0.137 (4)	0.071 (3)	0.086 (3)	0.005 (2)	−0.014 (4)	0.026 (3)
C3	0.124 (6)	0.083 (4)	0.214 (12)	0.017 (4)	0.097 (8)	0.004 (6)
C4	0.108 (3)	0.061 (2)	0.089 (4)	0.013 (3)	0.026 (3)	0.002 (2)
C5	0.055 (3)	0.046 (2)	0.056 (3)	0.002 (2)	0.008 (3)	−0.003 (3)
C6	0.059 (3)	0.058 (3)	0.047 (3)	0.014 (2)	−0.005 (3)	−0.008 (3)
C7	0.054 (3)	0.056 (3)	0.042 (3)	0.005 (2)	−0.006 (2)	−0.005 (2)
C8	0.036 (2)	0.045 (2)	0.040 (2)	−0.0024 (17)	−0.001 (2)	0.000 (2)
C9	0.055 (3)	0.056 (3)	0.060 (3)	0.020 (2)	−0.017 (3)	−0.011 (3)
C10	0.063 (3)	0.062 (3)	0.071 (4)	0.023 (3)	−0.016 (3)	0.000 (3)
C11	0.041 (2)	0.041 (2)	0.043 (3)	−0.0027 (18)	0.003 (2)	0.000 (2)
C12	0.047 (2)	0.046 (2)	0.032 (2)	0.0030 (18)	0.012 (2)	0.001 (2)
C13	0.041 (2)	0.046 (2)	0.041 (3)	0.0016 (19)	−0.003 (2)	−0.002 (2)
C14	0.057 (3)	0.063 (3)	0.039 (3)	0.001 (2)	−0.001 (3)	−0.005 (2)
C15	0.046 (2)	0.042 (2)	0.043 (3)	−0.0025 (18)	0.011 (2)	−0.002 (2)
C16	0.054 (2)	0.039 (2)	0.042 (3)	0.0018 (19)	0.002 (2)	−0.003 (2)
C17	0.036 (2)	0.056 (3)	0.045 (3)	−0.0036 (18)	−0.008 (2)	−0.005 (3)
C18	0.041 (2)	0.050 (2)	0.049 (3)	0.0076 (19)	−0.001 (2)	0.001 (3)
C19	0.070 (3)	0.037 (2)	0.075 (4)	0.003 (2)	−0.004 (3)	−0.008 (3)
C20	0.053 (3)	0.041 (2)	0.068 (3)	0.002 (2)	−0.008 (3)	−0.013 (3)
C21	0.062 (3)	0.066 (3)	0.065 (3)	0.014 (3)	−0.005 (3)	0.014 (3)
C22	0.081 (4)	0.160 (7)	0.117 (7)	0.070 (4)	0.024 (5)	0.044 (6)
C23	0.108 (5)	0.096 (4)	0.104 (6)	0.003 (4)	−0.055 (5)	0.004 (4)
C24	0.109 (5)	0.084 (4)	0.105 (6)	−0.001 (4)	−0.014 (5)	0.042 (5)

Geometric parameters (Å, º) top

N—O3	1.192 (5)	C12—H12A	0.9700
N—O2	1.231 (5)	C12—H12B	0.9700
N—C14	1.479 (6)	C13—C15	1.520 (6)
O1—C11	1.214 (5)	C13—C14	1.527 (7)
C1—C4	1.457 (9)	C13—H13A	0.9800
C1—H1A	0.9600	C14—H14A	0.9700
C1—H1B	0.9600	C14—H14B	0.9700
C1—H1C	0.9600	C15—C16	1.381 (6)
C2—C4	1.597 (11)	C15—C20	1.384 (6)
C2—H2A	0.9600	C16—C17	1.388 (6)
C2—H2B	0.9600	C16—H16A	0.9300
C2—H2C	0.9600	C17—C18	1.377 (6)
C3—C4	1.493 (9)	C17—H17A	0.9300
C3—H3A	0.9600	C18—C19	1.392 (7)
C3—H3B	0.9600	C18—C21	1.528 (7)
C3—H3C	0.9600	C19—C20	1.371 (7)
C4—C5	1.511 (7)	C19—H19A	0.9300
C5—C10	1.377 (8)	C20—H20A	0.9300
C5—C6	1.394 (7)	C21—C23	1.520 (9)
C6—C7	1.367 (6)	C21—C24	1.533 (8)
C6—H6A	0.9300	C21—C22	1.533 (9)
C7—C8	1.392 (6)	C22—H22A	0.9600
C7—H7A	0.9300	C22—H22B	0.9600
C8—C9	1.390 (6)	C22—H22C	0.9600
C8—C11	1.494 (6)	C23—H23A	0.9600
C9—C10	1.369 (6)	C23—H23B	0.9600
C9—H9A	0.9300	C23—H23C	0.9600
C10—H10A	0.9300	C24—H24A	0.9600
C11—C12	1.485 (6)	C24—H24B	0.9600
C12—C13	1.536 (6)	C24—H24C	0.9600

O3—N—O2	123.9 (5)	C15—C13—C14	112.7 (4)
O3—N—C14	119.3 (5)	C15—C13—C12	112.9 (4)
O2—N—C14	116.8 (5)	C14—C13—C12	112.7 (4)
C4—C1—H1A	109.5	C15—C13—H13A	105.9
C4—C1—H1B	109.5	C14—C13—H13A	105.9
H1A—C1—H1B	109.5	C12—C13—H13A	105.9
C4—C1—H1C	109.5	N—C14—C13	113.2 (4)
H1A—C1—H1C	109.5	N—C14—H14A	108.9
H1B—C1—H1C	109.5	C13—C14—H14A	108.9
C4—C2—H2A	109.5	N—C14—H14B	108.9
C4—C2—H2B	109.5	C13—C14—H14B	108.9
H2A—C2—H2B	109.5	H14A—C14—H14B	107.8
C4—C2—H2C	109.5	C16—C15—C20	116.6 (4)
H2A—C2—H2C	109.5	C16—C15—C13	123.4 (4)
H2B—C2—H2C	109.5	C20—C15—C13	119.9 (4)
C4—C3—H3A	109.5	C15—C16—C17	121.1 (4)
C4—C3—H3B	109.5	C15—C16—H16A	119.5
H3A—C3—H3B	109.5	C17—C16—H16A	119.5
C4—C3—H3C	109.5	C18—C17—C16	122.3 (4)
H3A—C3—H3C	109.5	C18—C17—H17A	118.8
H3B—C3—H3C	109.5	C16—C17—H17A	118.8
C1—C4—C3	111.3 (6)	C17—C18—C19	116.2 (4)
C1—C4—C5	112.2 (6)	C17—C18—C21	122.1 (4)
C3—C4—C5	112.4 (5)	C19—C18—C21	121.7 (4)
C1—C4—C2	104.4 (6)	C20—C19—C18	121.5 (4)
C3—C4—C2	104.4 (7)	C20—C19—H19A	119.2
C5—C4—C2	111.5 (6)	C18—C19—H19A	119.2
C10—C5—C6	115.9 (4)	C19—C20—C15	122.2 (5)
C10—C5—C4	121.6 (5)	C19—C20—H20A	118.9
C6—C5—C4	122.5 (5)	C15—C20—H20A	118.9
C7—C6—C5	121.8 (5)	C23—C21—C18	112.2 (4)
C7—C6—H6A	119.1	C23—C21—C24	106.0 (6)
C5—C6—H6A	119.1	C18—C21—C24	109.8 (5)
C6—C7—C8	121.2 (5)	C23—C21—C22	109.7 (6)
C6—C7—H7A	119.4	C18—C21—C22	108.1 (5)
C8—C7—H7A	119.4	C24—C21—C22	111.1 (5)
C9—C8—C7	117.4 (4)	C21—C22—H22A	109.5
C9—C8—C11	119.2 (4)	C21—C22—H22B	109.5
C7—C8—C11	123.3 (4)	H22A—C22—H22B	109.5
C10—C9—C8	120.1 (5)	C21—C22—H22C	109.5
C10—C9—H9A	120.0	H22A—C22—H22C	109.5
C8—C9—H9A	120.0	H22B—C22—H22C	109.5
C9—C10—C5	123.4 (5)	C21—C23—H23A	109.5
C9—C10—H10A	118.3	C21—C23—H23B	109.5
C5—C10—H10A	118.3	H23A—C23—H23B	109.5
O1—C11—C12	121.8 (4)	C21—C23—H23C	109.5
O1—C11—C8	119.6 (4)	H23A—C23—H23C	109.5
C12—C11—C8	118.6 (4)	H23B—C23—H23C	109.5
C11—C12—C13	114.5 (4)	C21—C24—H24A	109.5
C11—C12—H12A	108.6	C21—C24—H24B	109.5
C13—C12—H12A	108.6	H24A—C24—H24B	109.5
C11—C12—H12B	108.6	C21—C24—H24C	109.5
C13—C12—H12B	108.6	H24A—C24—H24C	109.5
H12A—C12—H12B	107.6	H24B—C24—H24C	109.5

C1—C4—C5—C10	−47.4 (8)	O3—N—C14—C13	−110.0 (5)
C3—C4—C5—C10	79.0 (8)	O2—N—C14—C13	66.9 (6)
C2—C4—C5—C10	−164.1 (6)	C15—C13—C14—N	−79.7 (5)
C1—C4—C5—C6	131.4 (6)	C12—C13—C14—N	49.5 (5)
C3—C4—C5—C6	−102.2 (8)	C14—C13—C15—C16	98.0 (5)
C2—C4—C5—C6	14.8 (8)	C12—C13—C15—C16	−31.1 (6)
C10—C5—C6—C7	2.6 (7)	C14—C13—C15—C20	−85.2 (6)
C4—C5—C6—C7	−176.3 (5)	C12—C13—C15—C20	145.7 (5)
C5—C6—C7—C8	−0.8 (7)	C20—C15—C16—C17	0.7 (7)
C6—C7—C8—C9	−1.8 (6)	C13—C15—C16—C17	177.6 (4)
C6—C7—C8—C11	175.8 (4)	C15—C16—C17—C18	−1.2 (8)
C7—C8—C9—C10	2.4 (7)	C16—C17—C18—C19	2.8 (7)
C11—C8—C9—C10	−175.2 (5)	C16—C17—C18—C21	−179.3 (5)
C8—C9—C10—C5	−0.6 (8)	C17—C18—C19—C20	−4.1 (8)
C6—C5—C10—C9	−1.9 (8)	C21—C18—C19—C20	178.0 (5)
C4—C5—C10—C9	177.0 (6)	C18—C19—C20—C15	4.0 (9)
C9—C8—C11—O1	−16.6 (6)	C16—C15—C20—C19	−2.1 (8)
C7—C8—C11—O1	165.9 (4)	C13—C15—C20—C19	−179.1 (5)
C9—C8—C11—C12	163.8 (4)	C17—C18—C21—C23	19.4 (8)
C7—C8—C11—C12	−13.7 (6)	C19—C18—C21—C23	−162.8 (6)
O1—C11—C12—C13	−0.1 (6)	C17—C18—C21—C24	137.1 (6)
C8—C11—C12—C13	179.5 (4)	C19—C18—C21—C24	−45.2 (8)
C11—C12—C13—C15	−162.8 (4)	C17—C18—C21—C22	−101.6 (7)
C11—C12—C13—C14	68.1 (5)	C19—C18—C21—C22	76.2 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.97	2.52	3.072 (5)	116

Symmetry code: (i) −x+1, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₃₁NO₃
M_r	381.50
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	20.440 (4), 17.500 (4), 6.1630 (12)
V (Å³)	2204.5 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.985, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	8662, 2247, 1527
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.181, 1.00
No. of reflections	2247
No. of parameters	247
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.32

Computer programs: CAD-4 Software (Enraf-Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.97	2.52	3.072 (5)	116

Symmetry code: (i) −x+1, −y+1, z+1/2.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

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