N-(4-tert-Butyl­benz­yl)phthalimide

Li, J.-S.; Simpson, J.; Li, X.

doi:10.1107/S1600536809025343

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1779

doi:10.1107/S1600536809025343

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N-(4-tert-Butylbenzyl)phthalimide

Jiang-Sheng Li,^a ^* Jim Simpson ^b and Xun Li ^a

^aSchool of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410004, People's Republic of China, and ^bDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
^*Correspondence e-mail: js_li@yahoo.com.cn

(Received 30 June 2009; accepted 30 June 2009; online 4 July 2009)

The molecule of the title compound [systematic name: 2-(4-tert-butylbenzyl)isoindoline-1,3-dione], C₁₉H₁₉NO₂, is V-shaped with a dihedral angle of 74.15 (7)° between the mean planes of the phthalimide unit and the benzene ring. The methyl groups of the tert-butyl substituent are disordered over two sets of positions, with an occupancy ratio of 0.700 (4):0.300 (4). In the crystal, intermolecular C—H⋯O hydrogen bonds link adjacent molecules into centrosymmetric dimers. An additional weak C—H⋯O contact, together with weak C—H⋯π and π–π interactions [centroid–centroid distance = 3.961 (2) Å] generate a three-dimensional network.

Related literature

For the synthesis, see: Xin et al. (2006 ). For related structures, see: Chen et al. (2006 ); Lü et al. (2006 ); Warzecha et al. (2006a ,b ,c ); Xin et al. (2006).For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₉H₁₉NO₂
M_r = 293.35
Trigonal, $[R \overline 3]$
a = 37.576 (7) Å
c = 6.2970 (16) Å
V = 7700 (3) Å³
Z = 18
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 294 K
0.24 × 0.22 × 0.18 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.983, T_max = 0.987
13205 measured reflections
3022 independent reflections
1574 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.139
S = 1.01
3022 reflections
232 parameters
117 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O2ⁱ	0.93	2.41	3.297 (3)	160
C9—H9B⋯O1ⁱⁱ	0.97	2.71	3.135 (3)	107
C5—H5A⋯Cg3ⁱⁱⁱ	0.93	2.94	3.771 (4)	149
Symmetry codes: (i) $[-x+{\script{5\over 3}}, -y+{\script{1\over 3}}, -z+{\script{7\over 3}}]$ ; (ii) $[-x+y+{\script{4\over 3}}, -x+{\script{2\over 3}}, z+{\script{2\over 3}}]$ ; (iii) $[-x+{\script{1\over 3}}, -y+{\script{2\over 3}}, -z+{\script{2\over 3}}]$ . Cg3 is the centroid of the C10–C15 benzene ring.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks gloabl, I. DOI: 10.1107/S1600536809025343/hb5020sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025343/hb5020Isup2.hkl

checkCIF report

Comment top

The molecular structure of (I) (Fig. 1) shows that the phthalimide ring system is almost planar, with the dihedral angle between the C2···C7 and N1/C1/C2/C7/C8 rings 1.26 (15) °. The molecule adopts a V-shape with a dihedral angle between the mean planes of the phthalimide group and the benzene ring of 74.12 (7) Å. Bond distances within the molecule are normal (Allen et al., 1987) and similar to those observed in comparable structures (Chen et al., 2006; Lü et al., 2006; Warzecha et al., 2006a,b,c; Xin et al., 2006).

In the crystal structure, complementary intermolecular C6—H6a···O2 hydrogen bonds link molecules into dimers (Table 1, Fig. 2). Additional weak C8—H9B···O1 and C—H···π contacts together with π-π interactions between the six-membered phthalimide rings (centroid-centroid separation 3.961 (2) Å; 1/3 - x,2/3 - y,2/3 - z) generate an extensive three-dimensional network structure, Fig. 3.

Related literature top

For the synthesis, see: Xin et al. (2006). For related structures, see: Chen et al. (2006); Lü et al. (2006); Warzecha et al. (2006a,b,c); Xin et al. (2006). Cg3 is the centroid of the C10–C15 benzene ring. For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was obtained by a literature method (Xin, et al., 2006). Colourless blocks of (I) were grown from an ethanol solution.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2009).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids drawn at the 30% probability level and H atoms shown as small spheres of arbitrary radius. Only the major disorder component of the disordered methyl groups is shown.
	Fig. 2. Centrosymmetric dimers of (I) formed by C—H···O hydrogen bonds drawn as dashed lines.
	Fig. 3. Crystal packing of (I) viewed down the c axis. Hydrogen bonds are drawn as dashed lines.

2-(4-tert-butylbenzyl)isoindoline-1,3-dione top

Crystal data top

C₁₉H₁₉NO₂	D_x = 1.139 Mg m⁻³
M_r = 293.35	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 2125 reflections
Hall symbol: -R 3	θ = 2.9–20.3°
a = 37.576 (7) Å	µ = 0.07 mm⁻¹
c = 6.2970 (16) Å	T = 294 K
V = 7700 (3) Å³	Block, colourless
Z = 18	0.24 × 0.22 × 0.18 mm
F(000) = 2808

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3022 independent reflections
Radiation source: fine-focus sealed tube	1574 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −44→44
T_min = 0.983, T_max = 0.987	k = −44→40
13205 measured reflections	l = −7→5

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)] = 0.051	H-atom parameters constrained
wR(F²) = 0.139	w = 1/[σ²(F_o²) + (0.067P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.007
3022 reflections	Δρ_max = 0.20 e Å⁻³
232 parameters	Δρ_min = −0.17 e Å⁻³
117 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0015 (3)

Crystal data top

C₁₉H₁₉NO₂	Z = 18
M_r = 293.35	Mo Kα radiation
Trigonal, R3	µ = 0.07 mm⁻¹
a = 37.576 (7) Å	T = 294 K
c = 6.2970 (16) Å	0.24 × 0.22 × 0.18 mm
V = 7700 (3) Å³

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3022 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1574 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.987	R_int = 0.060
13205 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	117 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.01	Δρ_max = 0.20 e Å⁻³
3022 reflections	Δρ_min = −0.17 e Å⁻³
232 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	Occ. (<1)
N1	0.74578 (6)	0.07689 (6)	0.8339 (3)	0.0624 (6)
O1	0.71269 (6)	0.06224 (6)	0.5108 (3)	0.0914 (7)
O2	0.78710 (6)	0.11049 (6)	1.1186 (3)	0.0878 (6)
C1	0.73592 (7)	0.08689 (8)	0.6388 (4)	0.0636 (7)
C2	0.75936 (7)	0.13258 (7)	0.6282 (4)	0.0592 (6)
C3	0.76152 (8)	0.15895 (9)	0.4692 (4)	0.0738 (8)
H3A	0.7463	0.1493	0.3448	0.089*
C4	0.78736 (9)	0.20036 (10)	0.5043 (5)	0.0857 (9)
H4A	0.7897	0.2190	0.4003	0.103*
C5	0.80973 (9)	0.21491 (9)	0.6882 (5)	0.0840 (9)
H5A	0.8267	0.2431	0.7061	0.101*
C6	0.80741 (8)	0.18844 (9)	0.8472 (4)	0.0742 (8)
H6A	0.8225	0.1981	0.9720	0.089*
C7	0.78172 (7)	0.14702 (8)	0.8123 (4)	0.0586 (6)
C8	0.77353 (8)	0.11164 (8)	0.9466 (4)	0.0637 (7)
C9	0.73037 (8)	0.03495 (8)	0.9110 (4)	0.0761 (8)
H9A	0.7041	0.0167	0.8446	0.091*
H9B	0.7261	0.0341	1.0632	0.091*
C10	0.76013 (7)	0.02033 (7)	0.8621 (4)	0.0633 (7)
C11	0.76087 (8)	0.00447 (8)	0.6666 (5)	0.0779 (8)
H11A	0.7418	0.0017	0.5640	0.093*
C12	0.78922 (8)	−0.00735 (8)	0.6194 (4)	0.0769 (8)
H12A	0.7887	−0.0181	0.4857	0.092*
C13	0.81833 (8)	−0.00375 (7)	0.7641 (4)	0.0648 (7)
C14	0.81715 (9)	0.01207 (8)	0.9605 (4)	0.0775 (8)
H14A	0.8363	0.0151	1.0630	0.093*
C15	0.78852 (9)	0.02358 (8)	1.0095 (4)	0.0755 (8)
H15A	0.7885	0.0337	1.1443	0.091*
C16	0.84998 (8)	−0.01645 (8)	0.7120 (4)	0.0776 (8)
C17	0.85716 (17)	−0.01769 (19)	0.4734 (6)	0.1105 (16)	0.700 (4)
H17A	0.8317	−0.0366	0.4056	0.166*	0.700 (4)
H17B	0.8769	−0.0265	0.4508	0.166*	0.700 (4)
H17C	0.8674	0.0092	0.4141	0.166*	0.700 (4)
C18	0.83567 (17)	−0.05907 (15)	0.8010 (9)	0.1127 (16)	0.700 (4)
H18A	0.8094	−0.0782	0.7410	0.169*	0.700 (4)
H18B	0.8332	−0.0586	0.9526	0.169*	0.700 (4)
H18C	0.8553	−0.0674	0.7657	0.169*	0.700 (4)
C19	0.89213 (15)	0.01404 (19)	0.8087 (9)	0.1309 (19)	0.700 (4)
H19A	0.8908	0.0112	0.9605	0.196*	0.700 (4)
H19B	0.8992	0.0416	0.7715	0.196*	0.700 (4)
H19C	0.9126	0.0083	0.7544	0.196*	0.700 (4)
C17'	0.8277 (4)	−0.0580 (3)	0.595 (2)	0.125 (3)	0.300 (4)
H17D	0.8080	−0.0786	0.6891	0.188*	0.300 (4)
H17E	0.8474	−0.0657	0.5511	0.188*	0.300 (4)
H17F	0.8138	−0.0556	0.4731	0.188*	0.300 (4)
C18'	0.8704 (4)	−0.0220 (4)	0.9090 (15)	0.106 (3)	0.300 (4)
H18D	0.8506	−0.0456	0.9871	0.160*	0.300 (4)
H18E	0.8806	0.0020	0.9970	0.160*	0.300 (4)
H18F	0.8927	−0.0260	0.8667	0.160*	0.300 (4)
C19'	0.8826 (3)	0.0180 (3)	0.578 (2)	0.115 (3)	0.300 (4)
H19D	0.8698	0.0235	0.4604	0.172*	0.300 (4)
H19E	0.9015	0.0100	0.5249	0.172*	0.300 (4)
H19F	0.8972	0.0423	0.6628	0.172*	0.300 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0547 (13)	0.0568 (13)	0.0710 (14)	0.0243 (11)	−0.0037 (10)	0.0023 (11)
O1	0.0771 (13)	0.0802 (13)	0.0980 (15)	0.0252 (11)	−0.0323 (11)	−0.0139 (11)
O2	0.0980 (15)	0.0980 (14)	0.0664 (13)	0.0482 (12)	−0.0134 (11)	−0.0046 (10)
C1	0.0501 (15)	0.0666 (18)	0.0722 (18)	0.0279 (14)	−0.0057 (13)	−0.0020 (14)
C2	0.0509 (15)	0.0649 (17)	0.0670 (17)	0.0330 (13)	0.0004 (13)	−0.0011 (14)
C3	0.0691 (18)	0.082 (2)	0.0766 (19)	0.0431 (17)	−0.0010 (14)	0.0084 (16)
C4	0.078 (2)	0.080 (2)	0.105 (2)	0.0436 (18)	0.0076 (18)	0.0199 (17)
C5	0.072 (2)	0.0623 (18)	0.116 (3)	0.0321 (16)	0.0029 (18)	0.0002 (19)
C6	0.0673 (18)	0.0686 (19)	0.088 (2)	0.0349 (15)	−0.0063 (14)	−0.0103 (16)
C7	0.0508 (15)	0.0620 (17)	0.0668 (17)	0.0310 (13)	0.0014 (12)	−0.0037 (13)
C8	0.0624 (16)	0.0716 (18)	0.0616 (17)	0.0369 (15)	−0.0027 (13)	−0.0051 (15)
C9	0.0628 (17)	0.0650 (17)	0.092 (2)	0.0255 (14)	0.0088 (14)	0.0128 (14)
C10	0.0587 (16)	0.0505 (15)	0.0716 (19)	0.0204 (13)	0.0006 (13)	0.0080 (12)
C11	0.0663 (18)	0.0742 (19)	0.082 (2)	0.0265 (15)	−0.0184 (14)	−0.0111 (15)
C12	0.077 (2)	0.0720 (18)	0.0724 (19)	0.0298 (16)	−0.0104 (15)	−0.0166 (14)
C13	0.0677 (17)	0.0519 (15)	0.0676 (17)	0.0244 (13)	0.0006 (14)	0.0029 (12)
C14	0.095 (2)	0.087 (2)	0.0638 (18)	0.0552 (18)	−0.0137 (14)	0.0018 (14)
C15	0.099 (2)	0.0821 (19)	0.0583 (17)	0.0551 (18)	−0.0020 (15)	0.0044 (13)
C16	0.0807 (18)	0.0794 (17)	0.0765 (17)	0.0429 (15)	0.0052 (13)	0.0025 (14)
C17	0.120 (3)	0.137 (3)	0.092 (3)	0.078 (3)	0.021 (2)	0.005 (2)
C18	0.131 (3)	0.106 (3)	0.130 (3)	0.081 (3)	0.026 (3)	0.029 (3)
C19	0.096 (3)	0.148 (4)	0.144 (4)	0.057 (3)	0.003 (3)	−0.036 (3)
C17'	0.124 (5)	0.123 (5)	0.132 (5)	0.065 (4)	0.006 (4)	−0.021 (4)
C18'	0.112 (5)	0.113 (5)	0.113 (5)	0.071 (4)	0.004 (4)	0.014 (4)
C19'	0.098 (4)	0.122 (5)	0.118 (5)	0.052 (4)	0.021 (4)	0.012 (4)

Geometric parameters (Å, º) top

N1—C8	1.391 (3)	C14—C15	1.380 (3)
N1—C1	1.388 (3)	C14—H14A	0.9300
N1—C9	1.464 (3)	C15—H15A	0.9300
O1—C1	1.209 (3)	C16—C19'	1.520 (7)
O2—C8	1.207 (3)	C16—C18	1.519 (4)
C1—C2	1.488 (3)	C16—C18'	1.526 (7)
C2—C7	1.374 (3)	C16—C17	1.531 (4)
C2—C3	1.382 (3)	C16—C17'	1.539 (7)
C3—C4	1.379 (4)	C16—C19	1.542 (5)
C3—H3A	0.9300	C17—H17A	0.9600
C4—C5	1.374 (4)	C17—H17B	0.9600
C4—H4A	0.9300	C17—H17C	0.9600
C5—C6	1.383 (4)	C18—H18A	0.9600
C5—H5A	0.9300	C18—H18B	0.9600
C6—C7	1.378 (3)	C18—H18C	0.9600
C6—H6A	0.9300	C19—H19A	0.9600
C7—C8	1.473 (3)	C19—H19B	0.9600
C9—C10	1.504 (3)	C19—H19C	0.9600
C9—H9A	0.9700	C17'—H17D	0.9600
C9—H9B	0.9700	C17'—H17E	0.9600
C10—C15	1.373 (3)	C17'—H17F	0.9600
C10—C11	1.374 (3)	C18'—H18D	0.9600
C11—C12	1.376 (4)	C18'—H18E	0.9600
C11—H11A	0.9300	C18'—H18F	0.9600
C12—C13	1.377 (3)	C19'—H19D	0.9600
C12—H12A	0.9300	C19'—H19E	0.9600
C13—C14	1.383 (3)	C19'—H19F	0.9600
C13—C16	1.522 (4)

C8—N1—C1	111.9 (2)	C18—C16—C18'	59.5 (5)
C8—N1—C9	123.3 (2)	C19'—C16—C13	106.1 (5)
C1—N1—C9	124.7 (2)	C18—C16—C13	109.3 (3)
O1—C1—N1	124.8 (2)	C18'—C16—C13	113.1 (5)
O1—C1—C2	129.7 (2)	C19'—C16—C17	53.2 (5)
N1—C1—C2	105.5 (2)	C18—C16—C17	107.8 (3)
C7—C2—C3	121.5 (2)	C18'—C16—C17	133.2 (5)
C7—C2—C1	108.1 (2)	C13—C16—C17	113.5 (3)
C3—C2—C1	130.4 (2)	C19'—C16—C17'	113.4 (7)
C4—C3—C2	116.7 (3)	C18—C16—C17'	51.7 (5)
C4—C3—H3A	121.7	C18'—C16—C17'	107.7 (7)
C2—C3—H3A	121.7	C13—C16—C17'	107.9 (5)
C5—C4—C3	122.0 (3)	C17—C16—C17'	61.0 (5)
C5—C4—H4A	119.0	C19'—C16—C19	59.7 (5)
C3—C4—H4A	119.0	C18—C16—C19	109.2 (4)
C4—C5—C6	121.2 (3)	C18'—C16—C19	51.8 (5)
C4—C5—H5A	119.4	C13—C16—C19	110.8 (3)
C6—C5—H5A	119.4	C17—C16—C19	106.2 (3)
C7—C6—C5	116.9 (3)	C17'—C16—C19	141.1 (5)
C7—C6—H6A	121.5	C16—C17—H17A	109.5
C5—C6—H6A	121.5	C16—C17—H17B	109.5
C2—C7—C6	121.7 (2)	H17A—C17—H17B	109.5
C2—C7—C8	108.5 (2)	C16—C17—H17C	109.5
C6—C7—C8	129.8 (2)	H17A—C17—H17C	109.5
O2—C8—N1	123.8 (2)	H17B—C17—H17C	109.5
O2—C8—C7	130.3 (2)	C16—C18—H18A	109.5
N1—C8—C7	106.0 (2)	C16—C18—H18B	109.5
N1—C9—C10	111.05 (19)	H18A—C18—H18B	109.5
N1—C9—H9A	109.4	C16—C18—H18C	109.5
C10—C9—H9A	109.4	H18A—C18—H18C	109.5
N1—C9—H9B	109.4	H18B—C18—H18C	109.5
C10—C9—H9B	109.4	C16—C19—H19A	109.5
H9A—C9—H9B	108.0	C16—C19—H19B	109.5
C15—C10—C11	117.5 (3)	C16—C19—H19C	109.5
C15—C10—C9	121.1 (3)	C16—C17'—H17D	109.5
C11—C10—C9	121.5 (2)	C16—C17'—H17E	109.5
C10—C11—C12	121.3 (2)	H17D—C17'—H17E	109.5
C10—C11—H11A	119.3	C16—C17'—H17F	109.5
C12—C11—H11A	119.3	H17D—C17'—H17F	109.5
C11—C12—C13	122.0 (3)	H17E—C17'—H17F	109.5
C11—C12—H12A	119.0	C16—C18'—H18D	109.5
C13—C12—H12A	119.0	C16—C18'—H18E	109.5
C12—C13—C14	116.0 (3)	H18D—C18'—H18E	109.5
C12—C13—C16	122.2 (2)	C16—C18'—H18F	109.5
C14—C13—C16	121.7 (2)	H18D—C18'—H18F	109.5
C15—C14—C13	122.2 (2)	H18E—C18'—H18F	109.5
C15—C14—H14A	118.9	C16—C19'—H19D	109.5
C13—C14—H14A	118.9	C16—C19'—H19E	109.5
C10—C15—C14	120.9 (2)	H19D—C19'—H19E	109.5
C10—C15—H15A	119.5	C16—C19'—H19F	109.5
C14—C15—H15A	119.5	H19D—C19'—H19F	109.5
C19'—C16—C18	144.5 (5)	H19E—C19'—H19F	109.5
C19'—C16—C18'	108.8 (7)

C8—N1—C1—O1	179.5 (2)	C8—N1—C9—C10	−83.0 (3)
C9—N1—C1—O1	1.8 (4)	C1—N1—C9—C10	94.5 (3)
C8—N1—C1—C2	−0.8 (3)	N1—C9—C10—C15	95.2 (3)
C9—N1—C1—C2	−178.57 (19)	N1—C9—C10—C11	−82.7 (3)
O1—C1—C2—C7	−179.8 (3)	C15—C10—C11—C12	−0.6 (4)
N1—C1—C2—C7	0.5 (2)	C9—C10—C11—C12	177.4 (2)
O1—C1—C2—C3	−1.3 (4)	C10—C11—C12—C13	−0.4 (4)
N1—C1—C2—C3	179.1 (2)	C11—C12—C13—C14	0.6 (4)
C7—C2—C3—C4	0.4 (4)	C11—C12—C13—C16	−179.5 (2)
C1—C2—C3—C4	−178.0 (2)	C12—C13—C14—C15	0.1 (4)
C2—C3—C4—C5	−0.4 (4)	C16—C13—C14—C15	−179.8 (2)
C3—C4—C5—C6	0.2 (4)	C11—C10—C15—C14	1.3 (4)
C4—C5—C6—C7	0.0 (4)	C9—C10—C15—C14	−176.7 (2)
C3—C2—C7—C6	−0.1 (4)	C13—C14—C15—C10	−1.1 (4)
C1—C2—C7—C6	178.5 (2)	C12—C13—C16—C19'	78.0 (6)
C3—C2—C7—C8	−178.8 (2)	C14—C13—C16—C19'	−102.1 (6)
C1—C2—C7—C8	−0.1 (2)	C12—C13—C16—C18	−98.6 (4)
C5—C6—C7—C2	0.0 (4)	C14—C13—C16—C18	81.3 (4)
C5—C6—C7—C8	178.3 (2)	C12—C13—C16—C18'	−162.8 (6)
C1—N1—C8—O2	−178.6 (2)	C14—C13—C16—C18'	17.1 (7)
C9—N1—C8—O2	−0.8 (4)	C12—C13—C16—C17	21.7 (4)
C1—N1—C8—C7	0.8 (3)	C14—C13—C16—C17	−158.4 (3)
C9—N1—C8—C7	178.6 (2)	C12—C13—C16—C17'	−43.8 (7)
C2—C7—C8—O2	179.0 (3)	C14—C13—C16—C17'	136.1 (6)
C6—C7—C8—O2	0.5 (4)	C12—C13—C16—C19	141.1 (4)
C2—C7—C8—N1	−0.4 (2)	C14—C13—C16—C19	−39.0 (4)
C6—C7—C8—N1	−178.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2ⁱ	0.93	2.41	3.297 (3)	160
C9—H9B···O1ⁱⁱ	0.97	2.71	3.135 (3)	107
C5—H5A···Cg3ⁱⁱⁱ	0.93	2.94	3.771 (4)	149

Symmetry codes: (i) −x+5/3, −y+1/3, −z+7/3; (ii) −x+y+4/3, −x+2/3, z+2/3; (iii) −x+1/3, −y+2/3, −z+2/3.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉NO₂
M_r	293.35
Crystal system, space group	Trigonal, R3
Temperature (K)	294
a, c (Å)	37.576 (7), 6.2970 (16)
V (Å³)	7700 (3)
Z	18
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.24 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.983, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	13205, 3022, 1574
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.139, 1.01
No. of reflections	3022
No. of parameters	232
No. of restraints	117
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.17

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2ⁱ	0.93	2.41	3.297 (3)	159.6
C9—H9B···O1ⁱⁱ	0.97	2.71	3.135 (3)	107.2
C5—H5A···Cg3ⁱⁱⁱ	0.93	2.94	3.771 (4)	149

Symmetry codes: (i) −x+5/3, −y+1/3, −z+7/3; (ii) −x+y+4/3, −x+2/3, z+2/3; (iii) −x+1/3, −y+2/3, −z+2/3.

Acknowledgements

This project was supported by the Changsha University of Science and Technology Talent Fund (Project No. 1004214)

References

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