(E)-Ethyl 4-[4-(diethyl­amino)styr­yl]benzoate

Yao, Y.-Y.; Lv, L.; Zhang, J.-X.; He, H.-W.

doi:10.1107/S1600536807065610

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o259

https://doi.org/10.1107/S1600536807065610

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(E)-Ethyl 4-[4-(diethylamino)styryl]benzoate

Yong-Yan Yao,^a Long Lv,^b Jun-Xiang Zhang ^b and Hong-Wu He ^a ^*

^aDepartment of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China, and ^bKey Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, People's Republic of China
^*Correspondence e-mail: he1208@mail.ccnu.edu.cn

(Received 14 November 2007; accepted 4 December 2007; online 12 December 2007)

In the title molecule, C₂₁H₂₅NO₂, the dihedral angle between the two benzene rings is 4.8 (2)°. Both the ethyl group of the ester group and one of the ethyl groups attached to the N atom are disordered over two sites, the approximate occupancies being 66:34 and 81:19, respectively. In the cystal structure, there are no direction-specific interactions.

Related literature

For related literature, see: Boggess et al. (1986 ); Iwase et al. (2003 ); Marynaoff & Reitz (1989 ); Reinhardt et al. (1998 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₂₅NO₂
M_r = 323.42
Orthorhombic, P n a 2₁
a = 7.8689 (11) Å
b = 8.8441 (11) Å
c = 26.404 (3) Å
V = 1837.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 292 (2) K
0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
10027 measured reflections
2043 independent reflections
1118 reflections with I > 2σ(I)
R_int = 0.121

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.112
S = 0.88
2043 reflections
261 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807065610/lh2575sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807065610/lh2575Isup2.hkl

checkCIF report

Comment top

Two-photon absorption (TPA) of organic materials has attracted much attention because of its various applications in photonics (Iwase et al., 2003). For these applications, it is important to prepare materials having a TPA cross-section at the wavelength of available laser sources (Reinhardt et al.,1998). We report here the structure of a new compound containing a TPA cross-section. The measurement of the TPA cross-section was performed by the nonlinear transmission method (Boggess et al., 1986).

In the molecular structure, the two benzene rings are almost coplanar with a dihedral angle of only 4.8 (2)° between them (Fig.1). The bond lengths and angles in the molecule are as expected (Allen et al., 1987).

In the crystal structure, no H-bonding, C—H···π, or π-π interactions are observed. The crystal is stablized only by van der Waals interactions.

Related literature top

For related literature, see: Boggess et al. (1986); Iwase et al. (2003); Marynaoff & Reitz (1989); Reinhardt et al. (1998). For bond-length data, see: Allen et al. (1987).

Experimental top

All reagents and solvents were used as obtained without further purification. The title compound was prepared according to literature procedure (Marynaoff et al., 1989). The solid product was dissolved in ether and the solution kept in air for one week. Crystals of of the title compound suitable for single-crystal X-ray diffraction analysis were grown by slow evaporation of the solution at the bottom of the vessel.

Structure description top

In the crystal structure, no H-bonding, C—H···π, or π-π interactions are observed. The crystal is stablized only by van der Waals interactions.

For related literature, see: Boggess et al. (1986); Iwase et al. (2003); Marynaoff & Reitz (1989); Reinhardt et al. (1998). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. The molecular structure showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The disorder is not shown.

(E)-Ethyl 4-[4-(diethylamino)styryl]benzoate top

Crystal data top

C₂₁H₂₅NO₂	F(000) = 696
M_r = 323.42	D_x = 1.169 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1356 reflections
a = 7.8689 (11) Å	θ = 2.6–26.4°
b = 8.8441 (11) Å	µ = 0.07 mm⁻¹
c = 26.404 (3) Å	T = 292 K
V = 1837.6 (4) Å³	Prism, orange
Z = 4	0.25 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	1118 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.121
Graphite monochromator	θ_max = 27.0°, θ_min = 2.4°
φ and ω scans	h = −10→8
10027 measured reflections	k = −11→9
2043 independent reflections	l = −33→33

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0476P)²] where P = (F_o² + 2F_c²)/3
S = 0.88	(Δ/σ)_max = 0.001
2043 reflections	Δρ_max = 0.15 e Å⁻³
261 parameters	Δρ_min = −0.14 e Å⁻³
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0030 (12)

Crystal data top

C₂₁H₂₅NO₂	V = 1837.6 (4) Å³
M_r = 323.42	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 7.8689 (11) Å	µ = 0.07 mm⁻¹
b = 8.8441 (11) Å	T = 292 K
c = 26.404 (3) Å	0.25 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	1118 reflections with I > 2σ(I)
10027 measured reflections	R_int = 0.121
2043 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	6 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 0.88	Δρ_max = 0.15 e Å⁻³
2043 reflections	Δρ_min = −0.14 e Å⁻³
261 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)
C1	0.3128 (5)	−0.0493 (5)	0.53178 (16)	0.0725 (10)
C2	0.4421 (5)	−0.0245 (4)	0.49197 (13)	0.0623 (9)
C3	0.4259 (5)	0.0791 (4)	0.45313 (14)	0.0757 (10)
H3	0.3282	0.1378	0.4508	0.091*
C4	0.5536 (5)	0.0961 (4)	0.41782 (14)	0.0755 (11)
H4	0.5395	0.1659	0.3918	0.091*
C5	0.7031 (4)	0.0120 (4)	0.41986 (13)	0.0600 (8)
C6	0.7157 (5)	−0.0933 (4)	0.45886 (14)	0.0700 (10)
H6	0.8119	−0.1540	0.4611	0.084*
C7	0.5887 (5)	−0.1088 (4)	0.49398 (14)	0.0716 (10)
H7	0.6022	−0.1786	0.5200	0.086*
C8	0.8356 (5)	0.0350 (4)	0.38217 (13)	0.0636 (9)
H8	0.8129	0.1074	0.3575	0.076*
C9	0.9833 (5)	−0.0335 (4)	0.37851 (14)	0.0652 (9)
H9	1.0058	−0.1062	0.4031	0.078*
C10	1.1164 (4)	−0.0102 (4)	0.34089 (13)	0.0576 (8)
C11	1.1104 (4)	0.0989 (3)	0.30381 (14)	0.0613 (9)
H11	1.0181	0.1646	0.3031	0.074*
C12	1.2348 (4)	0.1150 (4)	0.26768 (13)	0.0639 (9)
H12	1.2244	0.1901	0.2432	0.077*
C13	1.3780 (4)	0.0193 (4)	0.26715 (13)	0.0598 (9)
C14	1.3851 (5)	−0.0887 (4)	0.30509 (15)	0.0700 (9)
H14	1.4784	−0.1531	0.3067	0.084*
C15	1.2587 (5)	−0.1030 (4)	0.34012 (14)	0.0678 (9)
H15	1.2683	−0.1782	0.3646	0.081*
O2	0.1775 (4)	0.0376 (3)	0.52482 (12)	0.1001 (9)	0.663 (19)
C16	0.0545 (15)	0.0316 (14)	0.5682 (5)	0.076 (3)	0.663 (19)
H16A	−0.0044	−0.0648	0.5691	0.091*	0.663 (19)
H16B	0.1127	0.0462	0.6002	0.091*	0.663 (19)
C17	−0.0668 (12)	0.1578 (11)	0.5583 (5)	0.091 (4)	0.663 (19)
H17A	−0.0072	0.2524	0.5597	0.137*	0.663 (19)
H17B	−0.1548	0.1569	0.5835	0.137*	0.663 (19)
H17C	−0.1164	0.1453	0.5254	0.137*	0.663 (19)
O2'	0.1775 (4)	0.0376 (3)	0.52482 (12)	0.1001 (9)	0.337 (19)
C16'	0.009 (5)	0.025 (4)	0.5492 (11)	0.107 (10)	0.337 (19)
H16C	−0.0081	−0.0725	0.5651	0.128*	0.337 (19)
H16D	−0.0833	0.0452	0.5257	0.128*	0.337 (19)
C17'	0.029 (5)	0.149 (4)	0.5871 (11)	0.153 (12)	0.337 (19)
H17D	0.1412	0.1442	0.6015	0.230*	0.337 (19)
H17E	−0.0537	0.1371	0.6135	0.230*	0.337 (19)
H17F	0.0135	0.2448	0.5708	0.230*	0.337 (19)
C18	1.4744 (5)	0.1303 (4)	0.18598 (12)	0.0739 (10)
H18A	1.5819	0.1448	0.1687	0.089*
H18B	1.4349	0.2289	0.1970	0.089*
C19	1.3479 (5)	0.0668 (5)	0.14881 (15)	0.0886 (11)
H19A	1.3934	−0.0232	0.1337	0.133*
H19B	1.3255	0.1403	0.1229	0.133*
H19C	1.2441	0.0429	0.1662	0.133*
N1	1.5034 (4)	0.0366 (3)	0.23066 (12)	0.0738 (9)	0.811 (11)
C20	1.6626 (7)	−0.0480 (8)	0.2327 (3)	0.0763 (19)	0.811 (11)
H20A	1.6920	−0.0665	0.2679	0.092*	0.811 (11)
H20B	1.7525	0.0126	0.2179	0.092*	0.811 (11)
C21	1.6527 (8)	−0.1943 (8)	0.2057 (3)	0.110 (2)	0.811 (11)
H21A	1.5812	−0.2625	0.2243	0.166*	0.811 (11)
H21B	1.7645	−0.2368	0.2027	0.166*	0.811 (11)
H21C	1.6059	−0.1785	0.1725	0.166*	0.811 (11)
N1'	1.5034 (4)	0.0366 (3)	0.23066 (12)	0.0738 (9)	0.189 (11)
C20'	1.599 (3)	−0.1001 (14)	0.2184 (12)	0.083 (10)	0.189 (11)
H20C	1.5948	−0.1209	0.1823	0.100*	0.189 (11)
H20D	1.5548	−0.1867	0.2366	0.100*	0.189 (11)
C21'	1.775 (4)	−0.065 (3)	0.2346 (19)	0.113 (19)	0.189 (11)
H21D	1.7960	0.0410	0.2307	0.170*	0.189 (11)
H21E	1.8538	−0.1212	0.2141	0.170*	0.189 (11)
H21F	1.7893	−0.0932	0.2695	0.170*	0.189 (11)
O1	0.3244 (3)	−0.1352 (3)	0.56591 (12)	0.0978 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.064 (3)	0.076 (2)	0.078 (3)	−0.010 (2)	−0.002 (2)	−0.003 (2)
C2	0.061 (2)	0.063 (2)	0.063 (2)	−0.0091 (17)	−0.0039 (18)	0.0026 (18)
C3	0.065 (3)	0.087 (2)	0.075 (3)	0.014 (2)	0.010 (2)	0.005 (2)
C4	0.081 (3)	0.081 (2)	0.065 (2)	0.0169 (19)	0.006 (2)	0.0128 (19)
C5	0.069 (2)	0.0576 (18)	0.053 (2)	−0.0048 (16)	−0.0036 (19)	−0.0054 (16)
C6	0.060 (2)	0.078 (2)	0.072 (2)	0.0067 (17)	0.001 (2)	0.009 (2)
C7	0.071 (3)	0.073 (2)	0.071 (2)	0.0006 (19)	0.002 (2)	0.0177 (18)
C8	0.072 (3)	0.0589 (19)	0.059 (2)	−0.0024 (18)	0.0006 (18)	0.0005 (16)
C9	0.067 (2)	0.062 (2)	0.066 (2)	−0.0011 (18)	−0.0025 (19)	0.0040 (18)
C10	0.059 (2)	0.057 (2)	0.057 (2)	0.0024 (16)	−0.0021 (18)	−0.0014 (16)
C11	0.065 (2)	0.056 (2)	0.063 (2)	0.0083 (16)	0.0024 (19)	0.0015 (18)
C12	0.068 (2)	0.059 (2)	0.065 (2)	0.0102 (16)	0.0009 (19)	0.0066 (17)
C13	0.061 (2)	0.0586 (19)	0.059 (2)	0.0038 (17)	−0.0026 (19)	−0.0067 (17)
C14	0.065 (2)	0.073 (2)	0.071 (2)	0.0174 (18)	−0.009 (2)	0.007 (2)
C15	0.074 (2)	0.066 (2)	0.063 (2)	0.0069 (18)	−0.003 (2)	0.0139 (18)
O2	0.080 (2)	0.109 (2)	0.111 (2)	0.0086 (16)	0.0270 (18)	0.0163 (19)
C16	0.066 (6)	0.091 (7)	0.071 (8)	−0.006 (4)	0.011 (5)	−0.001 (6)
C17	0.083 (6)	0.080 (5)	0.110 (7)	0.008 (4)	0.036 (5)	0.004 (4)
O2'	0.080 (2)	0.109 (2)	0.111 (2)	0.0086 (16)	0.0270 (18)	0.0163 (19)
C16'	0.11 (2)	0.145 (19)	0.070 (16)	−0.042 (15)	0.007 (11)	−0.034 (13)
C17'	0.15 (3)	0.18 (2)	0.13 (2)	−0.044 (19)	0.050 (18)	−0.067 (18)
C18	0.071 (2)	0.080 (2)	0.071 (2)	−0.0031 (18)	0.007 (2)	0.005 (2)
C19	0.088 (3)	0.100 (3)	0.078 (2)	0.000 (2)	−0.004 (2)	0.005 (2)
N1	0.070 (2)	0.082 (2)	0.0688 (19)	0.0183 (16)	0.0061 (17)	0.0071 (17)
C20	0.050 (5)	0.090 (5)	0.090 (4)	0.003 (3)	0.002 (3)	0.002 (3)
C21	0.092 (4)	0.113 (5)	0.126 (5)	0.035 (4)	−0.013 (4)	−0.026 (4)
N1'	0.070 (2)	0.082 (2)	0.0688 (19)	0.0183 (16)	0.0061 (17)	0.0071 (17)
C20'	0.071 (17)	0.062 (19)	0.12 (2)	−0.031 (12)	0.046 (17)	−0.037 (13)
C21'	0.067 (19)	0.09 (2)	0.13 (6)	−0.012 (17)	−0.03 (3)	0.06 (2)
O1	0.079 (2)	0.120 (2)	0.095 (2)	−0.0136 (15)	0.0086 (16)	0.0296 (19)

Geometric parameters (Å, º) top

C1—O1	1.182 (4)	C16—H16A	0.9700
C1—O2	1.326 (4)	C16—H16B	0.9700
C1—C2	1.479 (5)	C17—H17A	0.9600
C2—C7	1.374 (5)	C17—H17B	0.9600
C2—C3	1.381 (5)	C17—H17C	0.9600
C3—C4	1.379 (5)	C16'—C17'	1.492 (8)
C3—H3	0.9300	C16'—H16C	0.9700
C4—C5	1.393 (5)	C16'—H16D	0.9700
C4—H4	0.9300	C17'—H17D	0.9600
C5—C6	1.392 (5)	C17'—H17E	0.9600
C5—C8	1.456 (4)	C17'—H17F	0.9600
C6—C7	1.370 (5)	C18—N1	1.460 (3)
C6—H6	0.9300	C18—C19	1.506 (5)
C7—H7	0.9300	C18—H18A	0.9700
C8—C9	1.314 (4)	C18—H18B	0.9700
C8—H8	0.9300	C19—H19A	0.9600
C9—C10	1.458 (5)	C19—H19B	0.9600
C9—H9	0.9300	C19—H19C	0.9600
C10—C11	1.376 (4)	N1—C20	1.460 (4)
C10—C15	1.389 (5)	C20—C21	1.480 (7)
C11—C12	1.374 (4)	C20—H20A	0.9700
C11—H11	0.9300	C20—H20B	0.9700
C12—C13	1.409 (4)	C21—H21A	0.9600
C12—H12	0.9300	C21—H21B	0.9600
C13—C14	1.386 (5)	C21—H21C	0.9600
C13—N1	1.388 (4)	C20'—C21'	1.481 (7)
C14—C15	1.364 (5)	C20'—H20C	0.9700
C14—H14	0.9300	C20'—H20D	0.9700
C15—H15	0.9300	C21'—H21D	0.9600
O2—C16	1.502 (14)	C21'—H21E	0.9600
C16—C17	1.492 (8)	C21'—H21F	0.9600

O1—C1—O2	122.7 (4)	C17—C16—O2	104.6 (8)
O1—C1—C2	125.7 (4)	C17—C16—H16A	110.8
O2—C1—C2	111.6 (4)	O2—C16—H16A	110.8
C7—C2—C3	117.8 (3)	C17—C16—H16B	110.8
C7—C2—C1	118.0 (3)	O2—C16—H16B	110.8
C3—C2—C1	124.2 (4)	H16A—C16—H16B	108.9
C4—C3—C2	120.5 (3)	C17'—C16'—H16C	112.1
C4—C3—H3	119.8	C17'—C16'—H16D	112.2
C2—C3—H3	119.8	H16C—C16'—H16D	109.8
C3—C4—C5	122.1 (3)	C16'—C17'—H17D	109.5
C3—C4—H4	119.0	C16'—C17'—H17E	109.5
C5—C4—H4	119.0	H17D—C17'—H17E	109.5
C6—C5—C4	116.5 (3)	C16'—C17'—H17F	109.5
C6—C5—C8	123.3 (3)	H17D—C17'—H17F	109.5
C4—C5—C8	120.3 (3)	H17E—C17'—H17F	109.5
C7—C6—C5	121.1 (3)	N1—C18—C19	114.7 (3)
C7—C6—H6	119.5	N1—C18—H18A	108.6
C5—C6—H6	119.5	C19—C18—H18A	108.6
C6—C7—C2	122.1 (3)	N1—C18—H18B	108.6
C6—C7—H7	118.9	C19—C18—H18B	108.6
C2—C7—H7	118.9	H18A—C18—H18B	107.6
C9—C8—C5	128.2 (3)	C18—C19—H19A	109.5
C9—C8—H8	115.9	C18—C19—H19B	109.5
C5—C8—H8	115.9	H19A—C19—H19B	109.5
C8—C9—C10	128.3 (3)	C18—C19—H19C	109.5
C8—C9—H9	115.8	H19A—C19—H19C	109.5
C10—C9—H9	115.8	H19B—C19—H19C	109.5
C11—C10—C15	115.6 (3)	C13—N1—C18	120.8 (3)
C11—C10—C9	124.0 (3)	C13—N1—C20	121.9 (3)
C15—C10—C9	120.4 (3)	C18—N1—C20	117.1 (4)
C12—C11—C10	122.8 (3)	N1—C20—C21	112.6 (6)
C12—C11—H11	118.6	N1—C20—H20A	109.1
C10—C11—H11	118.6	C21—C20—H20A	109.1
C11—C12—C13	120.9 (3)	N1—C20—H20B	109.1
C11—C12—H12	119.5	C21—C20—H20B	109.1
C13—C12—H12	119.5	H20A—C20—H20B	107.8
C14—C13—N1	123.3 (3)	C21'—C20'—H20C	110.9
C14—C13—C12	116.1 (3)	C21'—C20'—H20D	110.9
N1—C13—C12	120.6 (3)	H20C—C20'—H20D	108.9
C15—C14—C13	121.6 (3)	C20'—C21'—H21D	109.5
C15—C14—H14	119.2	C20'—C21'—H21E	109.5
C13—C14—H14	119.2	H21D—C21'—H21E	109.5
C14—C15—C10	122.9 (3)	C20'—C21'—H21F	109.5
C14—C15—H15	118.5	H21D—C21'—H21F	109.5
C10—C15—H15	118.5	H21E—C21'—H21F	109.5
C1—O2—C16	113.1 (4)

O1—C1—C2—C7	0.6 (5)	C9—C10—C11—C12	−177.6 (3)
O2—C1—C2—C7	−179.1 (3)	C10—C11—C12—C13	−0.5 (5)
O1—C1—C2—C3	−178.6 (4)	C11—C12—C13—C14	−0.6 (5)
O2—C1—C2—C3	1.6 (5)	C11—C12—C13—N1	−179.8 (3)
C7—C2—C3—C4	0.0 (5)	N1—C13—C14—C15	−179.6 (3)
C1—C2—C3—C4	179.3 (3)	C12—C13—C14—C15	1.3 (5)
C2—C3—C4—C5	−0.6 (6)	C13—C14—C15—C10	−1.0 (6)
C3—C4—C5—C6	1.5 (5)	C11—C10—C15—C14	−0.2 (5)
C3—C4—C5—C8	−179.2 (3)	C9—C10—C15—C14	178.4 (3)
C4—C5—C6—C7	−1.9 (5)	O1—C1—O2—C16	8.3 (8)
C8—C5—C6—C7	178.8 (3)	C2—C1—O2—C16	−172.0 (7)
C5—C6—C7—C2	1.4 (5)	C1—O2—C16—C17	168.7 (10)
C3—C2—C7—C6	−0.5 (5)	C14—C13—N1—C18	167.6 (3)
C1—C2—C7—C6	−179.8 (3)	C12—C13—N1—C18	−13.4 (5)
C6—C5—C8—C9	−0.9 (5)	C14—C13—N1—C20	−6.7 (6)
C4—C5—C8—C9	179.8 (3)	C12—C13—N1—C20	172.3 (5)
C5—C8—C9—C10	−179.8 (3)	C19—C18—N1—C13	−69.5 (4)
C8—C9—C10—C11	4.4 (5)	C19—C18—N1—C20	105.0 (5)
C8—C9—C10—C15	−174.1 (3)	C13—N1—C20—C21	89.9 (6)
C15—C10—C11—C12	0.9 (5)	C18—N1—C20—C21	−84.6 (6)

Experimental details

Crystal data
Chemical formula	C₂₁H₂₅NO₂
M_r	323.42
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	292
a, b, c (Å)	7.8689 (11), 8.8441 (11), 26.404 (3)
V (Å³)	1837.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10027, 2043, 1118
R_int	0.121
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.112, 0.88
No. of reflections	2043
No. of parameters	261
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

References

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