N,N-Dimethyl-3-(1-naphth-yloxy)-3-(2-thien-yl)propan-1-amine.

The title compound, C(19)H(21)NOS, is an inter-mediate for the synthesis of duloxetine hydro-chloride. In the mol-ecular structure, the thio-phene and naphthalene ring systems make a dihedral angle of 87.5°. All bond lengths and angles involving heteroatoms are as expected. In the crystal structure, no classical hydrogen bonds are found.

Related literature

For the preparation of duloxetine see: Deeter et al. (1990 ▶). For related hydroxy derivatives of the title mol­ecule, see: Tao, Bin et al. (2006 ▶); Tao, Li et al. (2006 ▶).

Experimental

Crystal data

C19H21NOS

M = 311.43

Monoclinic,

a = 9.6140 (19) Å

b = 18.578 (4) Å

c = 9.905 (2) Å

β = 104.53 (3)°

V = 1712.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 293 (2) K

0.40 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.928, T max = 0.981

3550 measured reflections

3352 independent reflections

2009 reflections with I > 2s(I)

R int = 0.038

3 standard reflections every 200 reflections intensity decay: <1%

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.194

S = 1.04

3352 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1981 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003255/bh2157sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003255/bh2157Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H21NOS	F000 = 664
Mr = 311.43	Dx = 1.208 Mg m−3
Monoclinic, P21/n	Melting point = 386–388 K
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71073 Å
a = 9.6140 (19) Å	Cell parameters from 25 reflections
b = 18.578 (4) Å	θ = 10–13º
c = 9.905 (2) Å	µ = 0.19 mm−1
β = 104.53 (3)º	T = 293 (2) K
V = 1712.5 (6) Å3	Block, brown
Z = 4	0.40 × 0.30 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.038
Radiation source: fine-focus sealed tube	θmax = 26.0º
Monochromator: graphite	θmin = 2.4º
T = 293(2) K	h = 0→11
ω/2θ scans	k = 0→22
Absorption correction: ψ scan(North et al., 1968)	l = −12→11
Tmin = 0.928, Tmax = 0.981	3 standard reflections
3550 measured reflections	every 200 reflections
3352 independent reflections	intensity decay: <1%
2009 reflections with I > 2s(I)

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)] = 0.070	H-atom parameters constrained
wR(F2) = 0.194	w = 1/[σ2(Fo2) + (0.08P)2 + 0.85P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3352 reflections	Δρmax = 0.45 e Å−3
199 parameters	Δρmin = −0.32 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
S	0.03342 (12)	0.25309 (6)	0.17997 (10)	0.0561 (3)
O	0.1693 (2)	0.34125 (12)	0.0007 (2)	0.0445 (6)
N	−0.1370 (3)	0.47356 (16)	−0.2560 (3)	0.0517 (8)
C1	−0.2401 (5)	0.4470 (2)	−0.3807 (5)	0.0777 (14)
H1A	−0.2777	0.4015	−0.3607	0.117*
H1B	−0.1929	0.4412	−0.4547	0.117*
H1C	−0.3173	0.4809	−0.4086	0.117*
C2	−0.0803 (5)	0.5421 (2)	−0.2843 (5)	0.0753 (13)
H2A	−0.0133	0.5593	−0.2016	0.113*
H2B	−0.1575	0.5760	−0.3123	0.113*
H2C	−0.0322	0.5367	−0.3577	0.113*
C3	−0.0227 (4)	0.4218 (2)	−0.2029 (4)	0.0517 (10)
H3A	0.0559	0.4461	−0.1383	0.062*
H3B	0.0131	0.4041	−0.2800	0.062*
C4	−0.0708 (4)	0.3584 (2)	−0.1295 (4)	0.0506 (10)
H4A	−0.1016	0.3758	−0.0493	0.061*
H4B	−0.1527	0.3357	−0.1924	0.061*
C5	0.0463 (4)	0.30309 (19)	−0.0816 (4)	0.0439 (9)
H5A	0.0711	0.2822	−0.1634	0.053*
C6	0.0029 (4)	0.24339 (18)	0.0033 (4)	0.0406 (8)
C7	−0.0719 (4)	0.17959 (18)	−0.0465 (4)	0.043
H7A	−0.0997	0.1649	−0.1392	0.052*
C8	−0.0976 (4)	0.1414 (2)	0.0708 (4)	0.0542 (10)
H8A	−0.1447	0.0973	0.0620	0.065*
C9	−0.0482 (4)	0.1743 (2)	0.1943 (4)	0.0510 (10)
H9A	−0.0580	0.1556	0.2785	0.061*
C10	0.3039 (4)	0.31259 (19)	0.0180 (3)	0.0403 (8)
C11	0.3328 (4)	0.2446 (2)	−0.0182 (4)	0.0498 (9)
H11A	0.2584	0.2131	−0.0572	0.060*
C12	0.4781 (5)	0.2225 (2)	0.0045 (4)	0.0574 (11)
H12A	0.4982	0.1762	−0.0211	0.069*
C13	0.5882 (5)	0.2673 (2)	0.0627 (4)	0.0603 (11)
H13A	0.6825	0.2515	0.0761	0.072*
C14	0.5612 (4)	0.3372 (2)	0.1027 (4)	0.0496 (10)
C15	0.6714 (4)	0.3854 (3)	0.1646 (4)	0.0677 (13)
H15A	0.7665	0.3704	0.1814	0.081*
C16	0.6431 (5)	0.4528 (3)	0.2002 (5)	0.0746 (13)
H16A	0.7185	0.4836	0.2397	0.089*
C17	0.5021 (5)	0.4765 (2)	0.1781 (4)	0.0655 (12)
H17A	0.4837	0.5230	0.2040	0.079*
C18	0.3900 (4)	0.4320 (2)	0.1186 (4)	0.0481 (9)
H18A	0.2961	0.4485	0.1038	0.058*
C19	0.4161 (4)	0.36147 (19)	0.0798 (3)	0.0409 (8)

	U11	U22	U33	U12	U13	U23
S	0.0651 (7)	0.0585 (6)	0.0425 (5)	−0.0028 (5)	0.0094 (5)	−0.0023 (5)
O	0.0335 (13)	0.0410 (14)	0.0566 (15)	−0.0007 (11)	0.0070 (11)	−0.0068 (11)
N	0.0482 (19)	0.0464 (18)	0.058 (2)	0.0008 (15)	0.0083 (15)	0.0088 (15)
C1	0.065 (3)	0.070 (3)	0.081 (3)	−0.003 (2)	−0.011 (2)	0.018 (3)
C2	0.074 (3)	0.054 (3)	0.095 (4)	−0.003 (2)	0.017 (3)	0.013 (3)
C3	0.041 (2)	0.055 (2)	0.057 (2)	−0.0018 (18)	0.0077 (18)	0.0090 (19)
C4	0.040 (2)	0.055 (2)	0.053 (2)	0.0009 (18)	0.0033 (17)	0.0086 (19)
C5	0.044 (2)	0.045 (2)	0.0414 (19)	−0.0021 (17)	0.0088 (16)	−0.0027 (16)
C6	0.0393 (19)	0.044 (2)	0.0367 (17)	0.0071 (16)	0.0068 (14)	0.0008 (16)
C7	0.043	0.043	0.043	0.000	0.011	0.000
C8	0.060 (3)	0.041 (2)	0.059 (3)	−0.0030 (19)	0.012 (2)	−0.0004 (19)
C9	0.062 (3)	0.047 (2)	0.046 (2)	0.0077 (19)	0.0170 (19)	0.0069 (18)
C10	0.0380 (19)	0.048 (2)	0.0372 (19)	0.0080 (16)	0.0127 (15)	0.0072 (16)
C11	0.055 (2)	0.050 (2)	0.048 (2)	0.0039 (19)	0.0182 (18)	0.0050 (19)
C12	0.069 (3)	0.056 (2)	0.055 (2)	0.022 (2)	0.029 (2)	0.011 (2)
C13	0.050 (2)	0.084 (3)	0.049 (2)	0.025 (2)	0.0167 (19)	0.016 (2)
C14	0.041 (2)	0.070 (3)	0.039 (2)	0.0091 (19)	0.0118 (17)	0.0115 (19)
C15	0.039 (2)	0.103 (4)	0.059 (3)	−0.002 (2)	0.008 (2)	0.005 (3)
C16	0.051 (3)	0.101 (4)	0.067 (3)	−0.019 (3)	0.004 (2)	−0.007 (3)
C17	0.064 (3)	0.060 (3)	0.069 (3)	−0.009 (2)	0.011 (2)	−0.010 (2)
C18	0.046 (2)	0.052 (2)	0.046 (2)	−0.0025 (18)	0.0120 (17)	0.0017 (18)
C19	0.0399 (19)	0.050 (2)	0.0324 (18)	0.0023 (17)	0.0085 (15)	0.0062 (16)

S—C6	1.709 (3)	C7—H7A	0.9300
S—C9	1.683 (4)	C8—C9	1.343 (5)
O—C10	1.370 (4)	C8—H8A	0.9300
O—C5	1.443 (4)	C9—H9A	0.9300
N—C2	1.440 (5)	C10—C11	1.360 (5)
N—C3	1.455 (5)	C10—C19	1.425 (5)
N—C1	1.462 (5)	C11—C12	1.419 (5)
C1—H1A	0.9600	C11—H11A	0.9300
C1—H1B	0.9600	C12—C13	1.357 (6)
C1—H1C	0.9600	C12—H12A	0.9300
C2—H2A	0.9600	C13—C14	1.400 (5)
C2—H2B	0.9600	C13—H13A	0.9300
C2—H2C	0.9600	C14—C15	1.406 (6)
C3—C4	1.517 (5)	C14—C19	1.429 (5)
C3—H3A	0.9700	C15—C16	1.345 (6)
C3—H3B	0.9700	C15—H15A	0.9300
C4—C5	1.511 (5)	C16—C17	1.390 (6)
C4—H4A	0.9700	C16—H16A	0.9300
C4—H4B	0.9700	C17—C18	1.369 (5)
C5—C6	1.513 (5)	C17—H17A	0.9300
C5—H5A	0.9800	C18—C19	1.405 (5)
C6—C7	1.410 (5)	C18—H18A	0.9300
C7—C8	1.435 (5)
C9—S—C6	91.74 (18)	C6—C7—H7A	126.0
C10—O—C5	119.6 (3)	C8—C7—H7A	126.0
C2—N—C3	111.4 (3)	C9—C8—C7	114.8 (3)
C2—N—C1	110.1 (3)	C9—C8—H8A	122.6
C3—N—C1	111.9 (3)	C7—C8—H8A	122.6
N—C1—H1A	109.5	C8—C9—S	112.6 (3)
N—C1—H1B	109.5	C8—C9—H9A	123.7
H1A—C1—H1B	109.5	S—C9—H9A	123.7
N—C1—H1C	109.5	C11—C10—O	125.2 (3)
H1A—C1—H1C	109.5	C11—C10—C19	121.4 (3)
H1B—C1—H1C	109.5	O—C10—C19	113.3 (3)
N—C2—H2A	109.5	C10—C11—C12	119.1 (4)
N—C2—H2B	109.5	C10—C11—H11A	120.5
H2A—C2—H2B	109.5	C12—C11—H11A	120.5
N—C2—H2C	109.5	C13—C12—C11	121.4 (4)
H2A—C2—H2C	109.5	C13—C12—H12A	119.3
H2B—C2—H2C	109.5	C11—C12—H12A	119.3
N—C3—C4	113.1 (3)	C12—C13—C14	120.6 (4)
N—C3—H3A	109.0	C12—C13—H13A	119.7
C4—C3—H3A	109.0	C14—C13—H13A	119.7
N—C3—H3B	109.0	C13—C14—C15	122.7 (4)
C4—C3—H3B	109.0	C13—C14—C19	119.4 (4)
H3A—C3—H3B	107.8	C15—C14—C19	117.8 (4)
C5—C4—C3	112.7 (3)	C16—C15—C14	121.8 (4)
C5—C4—H4A	109.1	C16—C15—H15A	119.1
C3—C4—H4A	109.1	C14—C15—H15A	119.1
C5—C4—H4B	109.1	C15—C16—C17	120.5 (4)
C3—C4—H4B	109.1	C15—C16—H16A	119.8
H4A—C4—H4B	107.8	C17—C16—H16A	119.8
O—C5—C4	106.5 (3)	C18—C17—C16	120.5 (4)
O—C5—C6	110.3 (3)	C18—C17—H17A	119.8
C4—C5—C6	112.7 (3)	C16—C17—H17A	119.8
O—C5—H5A	109.1	C17—C18—C19	120.4 (4)
C4—C5—H5A	109.1	C17—C18—H18A	119.8
C6—C5—H5A	109.1	C19—C18—H18A	119.8
C7—C6—C5	127.5 (3)	C18—C19—C10	122.9 (3)
C7—C6—S	112.9 (3)	C18—C19—C14	119.0 (3)
C5—C6—S	119.4 (3)	C10—C19—C14	118.1 (3)
C6—C7—C8	108.0 (3)
C2—N—C3—C4	161.7 (4)	C19—C10—C11—C12	−0.9 (5)
C1—N—C3—C4	−74.6 (4)	C10—C11—C12—C13	0.7 (6)
N—C3—C4—C5	176.9 (3)	C11—C12—C13—C14	0.2 (6)
C10—O—C5—C4	−157.5 (3)	C12—C13—C14—C15	179.4 (4)
C10—O—C5—C6	80.0 (4)	C12—C13—C14—C19	−1.0 (6)
C3—C4—C5—O	53.6 (4)	C13—C14—C15—C16	178.9 (4)
C3—C4—C5—C6	174.6 (3)	C19—C14—C15—C16	−0.8 (6)
O—C5—C6—C7	−154.8 (3)	C14—C15—C16—C17	0.9 (7)
C4—C5—C6—C7	86.3 (4)	C15—C16—C17—C18	−0.7 (7)
O—C5—C6—S	30.0 (4)	C16—C17—C18—C19	0.4 (6)
C4—C5—C6—S	−88.8 (3)	C17—C18—C19—C10	179.7 (3)
C9—S—C6—C7	0.6 (3)	C17—C18—C19—C14	−0.3 (5)
C9—S—C6—C5	176.4 (3)	C11—C10—C19—C18	−179.9 (3)
C5—C6—C7—C8	−176.3 (3)	O—C10—C19—C18	−0.1 (5)
S—C6—C7—C8	−0.8 (4)	C11—C10—C19—C14	0.2 (5)
C6—C7—C8—C9	0.7 (5)	O—C10—C19—C14	180.0 (3)
C7—C8—C9—S	−0.3 (4)	C13—C14—C19—C18	−179.2 (3)
C6—S—C9—C8	−0.2 (3)	C15—C14—C19—C18	0.5 (5)
C5—O—C10—C11	−10.8 (5)	C13—C14—C19—C10	0.8 (5)
C5—O—C10—C19	169.4 (3)	C15—C14—C19—C10	−179.6 (3)
O—C10—C11—C12	179.3 (3)