(±)-3-[2-(Methyl­sulfan­yl)eth­yl]-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine

Yin, Z.-G.; Qian, H.-Y.; Chen, Y.-Z.; Feng, Y.-L.

doi:10.1107/S1600536807051896

(±)-3-[2-(Methylsulfanyl)ethyl]-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine

Z.-G. Yin, H.-Y. Qian, Y.-Z. Chen and Y.-L. Feng

In the title compound, C₂₁H₂₁NOS, the oxazine ring is not planar and displays a half-chair conformation. The phenyl and naphthalene ring systems make a dihedral angle of 78.65 (7)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051896/dn2249sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051896/dn2249Isup2.hkl Contains datablock I

CCDC reference: 667466

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.042
wR factor = 0.122
Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.79 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.35 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C15    -   C16     ..       5.83 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C11    = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C18    = ...          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

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

Comment top

The oxazine derivatives present various applications and widespread potential biological and pharmacological activities such as antimicrobial(Mahajan et al., 1991), antitumor(Katayama & Oshiyama, 1997) and antihistaminic (Mishra et al., 1998). In view of these important properties, the crystal structure of the title compound, (I), has been determined.

The oxazine ring is not planar and displays an half-chair conformation with the puckering parameters: Q= 0.445 (2) Å, θ = 52.9 (2)° and φ= 268.0 (2) °(Cremer & Pople, 1975). The dihedral angle between the benzene ring and the naphthalene ring is 78.65 (7). The bond lengths C18—N1 and C18—O1 in the oxazine ring are 1.421 (2) Å and 1.458 (2) Å respectively.

Related literature top

For related literature, see: Katayama & Oshiyama (1997); Mahajan et al. (1991); Mishra et al. (1998); Cremer & Pople (1975).

Experimental top

1-(amino(phenyl)methyl)naphthalen-2-ol (1 mmol, 0.249 g) was dissolved in anhydrous methanol, the mixture was stirred for several minitutes, 3-(methylthio)propanal (1 mmol 0.104 g) in methanol (8 ml) was added dropwise and the mixture was stirred at room temperature for 2 h. The product was isolated and recrystallized in dichloromethane, colorless single crystals of (I) was obtained after 5 d.

Structure description top

For related literature, see: Katayama & Oshiyama (1997); Mahajan et al. (1991); Mishra et al. (1998); Cremer & Pople (1975).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

Fig. 1. Molecular view of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

(±)-3-[2-(Methylsulfanyl)ethyl]-1-phenyl-2,3-dihydro-1H- naphtho[1,2-e][1,3]oxazine top

Crystal data top

C₂₁H₂₁NOS	F(000) = 712
M_r = 335.45	D_x = 1.263 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1680 reflections
a = 7.2753 (7) Å	θ = 2.5–24.2°
b = 14.9201 (13) Å	µ = 0.19 mm⁻¹
c = 16.4212 (15) Å	T = 298 K
β = 98.375 (1)°	Block, colorless
V = 1763.5 (3) Å³	0.27 × 0.23 × 0.23 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3655 independent reflections
Radiation source: fine-focus sealed tube	2876 reflections with I > 2/s(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 26.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→9
T_min = 0.951, T_max = 0.959	k = −18→18
20758 measured reflections	l = −20→20

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0608P)² + 0.3947P] where P = (F_o² + 2F_c²)/3
3655 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.22 e Å⁻³
1 restraint	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₁H₂₁NOS	V = 1763.5 (3) Å³
M_r = 335.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.2753 (7) Å	µ = 0.19 mm⁻¹
b = 14.9201 (13) Å	T = 298 K
c = 16.4212 (15) Å	0.27 × 0.23 × 0.23 mm
β = 98.375 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3655 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2876 reflections with I > 2/s(I)
T_min = 0.951, T_max = 0.959	R_int = 0.027
20758 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.22 e Å⁻³
3655 reflections	Δρ_min = −0.30 e Å⁻³
221 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
S1	0.14238 (7)	0.88480 (4)	0.31146 (3)	0.06027 (18)
O1	0.25196 (16)	0.89873 (8)	0.05231 (7)	0.0504 (3)
N1	0.58022 (19)	0.87665 (9)	0.08898 (8)	0.0436 (3)
H1	0.599 (3)	0.9329 (7)	0.0971 (12)	0.065*
C1	0.4372 (2)	0.87861 (9)	−0.05684 (9)	0.0386 (3)
C2	0.2738 (2)	0.90140 (10)	−0.02920 (10)	0.0418 (4)
C3	0.1183 (2)	0.93206 (12)	−0.08314 (11)	0.0511 (4)
H3	0.0104	0.9479	−0.0625	0.061*
C4	0.1246 (2)	0.93857 (12)	−0.16469 (11)	0.0539 (4)
H4	0.0210	0.9590	−0.1997	0.065*
C5	0.2875 (3)	0.91463 (11)	−0.19755 (10)	0.0478 (4)
C6	0.2985 (3)	0.92130 (12)	−0.28267 (11)	0.0602 (5)
H6	0.1968	0.9428	−0.3182	0.072*
C7	0.4539 (4)	0.89713 (13)	−0.31338 (11)	0.0663 (6)
H7	0.4576	0.9009	−0.3696	0.080*
C8	0.6092 (3)	0.86646 (13)	−0.26024 (12)	0.0624 (5)
H8	0.7159	0.8503	−0.2816	0.075*
C9	0.6063 (3)	0.85996 (12)	−0.17763 (11)	0.0510 (4)
H9	0.7111	0.8396	−0.1434	0.061*
C10	0.4449 (2)	0.88390 (9)	−0.14325 (9)	0.0405 (3)
C11	0.6056 (2)	0.85344 (10)	0.00404 (9)	0.0402 (3)
H11	0.7098	0.8893	−0.0095	0.048*
C12	0.6629 (2)	0.75561 (11)	0.00149 (9)	0.0424 (4)
C13	0.5476 (2)	0.69028 (11)	−0.03684 (10)	0.0487 (4)
H13	0.4308	0.7061	−0.0639	0.058*
C14	0.6025 (3)	0.60134 (12)	−0.03570 (13)	0.0643 (5)
H14	0.5230	0.5582	−0.0621	0.077*
C15	0.7718 (4)	0.57695 (16)	0.00378 (14)	0.0783 (7)
H15	0.8073	0.5170	0.0057	0.094*
C16	0.8897 (4)	0.64095 (19)	0.04070 (16)	0.0933 (9)
H16	1.0070	0.6245	0.0667	0.112*
C17	0.8365 (3)	0.73032 (16)	0.03989 (13)	0.0729 (6)
H17	0.9182	0.7733	0.0653	0.087*
C18	0.4003 (2)	0.85325 (11)	0.10595 (9)	0.0440 (4)
H18	0.3838	0.7884	0.0985	0.053*
C19	0.3727 (2)	0.87701 (12)	0.19314 (10)	0.0497 (4)
H19A	0.4702	0.8493	0.2316	0.060*
H19B	0.3826	0.9414	0.2004	0.060*
C20	0.1860 (3)	0.84608 (13)	0.21210 (11)	0.0563 (5)
H20A	0.1815	0.7811	0.2108	0.068*
H20B	0.0893	0.8683	0.1700	0.068*
C21	−0.0719 (4)	0.8270 (2)	0.31290 (18)	0.1074 (10)
H21A	−0.1599	0.8456	0.2666	0.161*
H21B	−0.1196	0.8408	0.3630	0.161*
H21C	−0.0515	0.7636	0.3099	0.161*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0599 (3)	0.0828 (4)	0.0395 (3)	0.0056 (2)	0.0120 (2)	−0.0013 (2)
O1	0.0468 (6)	0.0636 (7)	0.0432 (6)	0.0048 (5)	0.0144 (5)	0.0004 (5)
N1	0.0464 (8)	0.0453 (7)	0.0394 (7)	−0.0052 (6)	0.0077 (6)	−0.0083 (6)
C1	0.0437 (8)	0.0321 (7)	0.0406 (8)	−0.0016 (6)	0.0084 (6)	−0.0004 (6)
C2	0.0453 (9)	0.0400 (8)	0.0409 (8)	−0.0017 (7)	0.0093 (7)	−0.0014 (6)
C3	0.0421 (9)	0.0542 (10)	0.0571 (10)	0.0030 (7)	0.0076 (8)	−0.0020 (8)
C4	0.0503 (10)	0.0517 (10)	0.0559 (10)	0.0028 (8)	−0.0052 (8)	0.0006 (8)
C5	0.0609 (10)	0.0382 (8)	0.0428 (9)	−0.0040 (7)	0.0025 (7)	−0.0008 (7)
C6	0.0847 (14)	0.0532 (10)	0.0393 (9)	−0.0036 (10)	−0.0025 (9)	0.0021 (8)
C7	0.1079 (17)	0.0558 (11)	0.0370 (9)	−0.0052 (11)	0.0160 (10)	−0.0007 (8)
C8	0.0847 (14)	0.0576 (11)	0.0508 (11)	0.0023 (10)	0.0295 (10)	−0.0011 (8)
C9	0.0600 (11)	0.0483 (9)	0.0473 (9)	0.0025 (8)	0.0167 (8)	0.0011 (7)
C10	0.0507 (9)	0.0324 (7)	0.0392 (8)	−0.0028 (6)	0.0087 (7)	−0.0014 (6)
C11	0.0405 (8)	0.0431 (8)	0.0377 (8)	−0.0040 (6)	0.0079 (6)	−0.0028 (6)
C12	0.0455 (8)	0.0491 (9)	0.0332 (7)	0.0069 (7)	0.0082 (6)	0.0008 (6)
C13	0.0508 (9)	0.0431 (9)	0.0530 (10)	0.0024 (7)	0.0105 (8)	0.0024 (7)
C14	0.0826 (15)	0.0451 (10)	0.0696 (13)	0.0042 (9)	0.0255 (11)	0.0011 (9)
C15	0.1074 (19)	0.0586 (12)	0.0715 (14)	0.0345 (13)	0.0214 (13)	0.0102 (11)
C16	0.0943 (19)	0.102 (2)	0.0754 (15)	0.0557 (16)	−0.0145 (13)	−0.0026 (14)
C17	0.0623 (12)	0.0832 (15)	0.0656 (12)	0.0228 (11)	−0.0164 (10)	−0.0176 (11)
C18	0.0497 (9)	0.0422 (8)	0.0405 (8)	−0.0015 (7)	0.0081 (7)	−0.0018 (6)
C19	0.0557 (10)	0.0533 (10)	0.0413 (9)	−0.0024 (8)	0.0110 (8)	−0.0036 (7)
C20	0.0648 (11)	0.0593 (11)	0.0477 (10)	−0.0080 (9)	0.0184 (8)	−0.0074 (8)
C21	0.099 (2)	0.131 (2)	0.106 (2)	−0.0306 (18)	0.0601 (17)	−0.0140 (18)

Geometric parameters (Å, º) top

S1—C21	1.784 (3)	C9—H9	0.9300
S1—C20	1.8020 (17)	C11—C12	1.520 (2)
O1—C2	1.3714 (19)	C11—H11	0.9800
O1—C18	1.457 (2)	C12—C13	1.377 (2)
N1—C18	1.421 (2)	C12—C17	1.380 (2)
N1—C11	1.4745 (19)	C13—C14	1.385 (2)
N1—H1	0.857 (9)	C13—H13	0.9300
C1—C2	1.375 (2)	C14—C15	1.355 (3)
C1—C10	1.430 (2)	C14—H14	0.9300
C1—C11	1.511 (2)	C15—C16	1.365 (4)
C2—C3	1.408 (2)	C15—H15	0.9300
C3—C4	1.350 (2)	C16—C17	1.388 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.417 (3)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.516 (2)
C5—C6	1.415 (2)	C18—H18	0.9800
C5—C10	1.421 (2)	C19—C20	1.510 (2)
C6—C7	1.352 (3)	C19—H19A	0.9700
C6—H6	0.9300	C19—H19B	0.9700
C7—C8	1.400 (3)	C20—H20A	0.9700
C7—H7	0.9300	C20—H20B	0.9700
C8—C9	1.363 (2)	C21—H21A	0.9600
C8—H8	0.9300	C21—H21B	0.9600
C9—C10	1.421 (2)	C21—H21C	0.9600

C21—S1—C20	97.27 (11)	C13—C12—C11	122.72 (14)
C2—O1—C18	115.00 (12)	C17—C12—C11	119.12 (16)
C18—N1—C11	111.93 (12)	C12—C13—C14	121.08 (18)
C18—N1—H1	109.7 (14)	C12—C13—H13	119.5
C11—N1—H1	109.8 (13)	C14—C13—H13	119.5
C2—C1—C10	118.30 (14)	C15—C14—C13	120.3 (2)
C2—C1—C11	119.96 (13)	C15—C14—H14	119.9
C10—C1—C11	121.67 (13)	C13—C14—H14	119.9
O1—C2—C1	122.92 (14)	C14—C15—C16	119.5 (2)
O1—C2—C3	115.26 (14)	C14—C15—H15	120.2
C1—C2—C3	121.79 (15)	C16—C15—H15	120.2
C4—C3—C2	120.46 (16)	C15—C16—C17	120.8 (2)
C4—C3—H3	119.8	C15—C16—H16	119.6
C2—C3—H3	119.8	C17—C16—H16	119.6
C3—C4—C5	120.71 (16)	C12—C17—C16	120.2 (2)
C3—C4—H4	119.6	C12—C17—H17	119.9
C5—C4—H4	119.6	C16—C17—H17	119.9
C6—C5—C4	121.93 (17)	N1—C18—O1	112.90 (13)
C6—C5—C10	119.11 (17)	N1—C18—C19	112.33 (13)
C4—C5—C10	118.96 (15)	O1—C18—C19	105.88 (13)
C7—C6—C5	121.34 (19)	N1—C18—H18	108.5
C7—C6—H6	119.3	O1—C18—H18	108.5
C5—C6—H6	119.3	C19—C18—H18	108.5
C6—C7—C8	119.82 (17)	C20—C19—C18	111.72 (14)
C6—C7—H7	120.1	C20—C19—H19A	109.3
C8—C7—H7	120.1	C18—C19—H19A	109.3
C9—C8—C7	121.03 (19)	C20—C19—H19B	109.3
C9—C8—H8	119.5	C18—C19—H19B	109.3
C7—C8—H8	119.5	H19A—C19—H19B	107.9
C8—C9—C10	120.73 (18)	C19—C20—S1	111.79 (12)
C8—C9—H9	119.6	C19—C20—H20A	109.3
C10—C9—H9	119.6	S1—C20—H20A	109.3
C9—C10—C5	117.96 (15)	C19—C20—H20B	109.3
C9—C10—C1	122.29 (15)	S1—C20—H20B	109.3
C5—C10—C1	119.75 (14)	H20A—C20—H20B	107.9
N1—C11—C1	111.50 (12)	S1—C21—H21A	109.5
N1—C11—C12	108.91 (12)	S1—C21—H21B	109.5
C1—C11—C12	114.81 (13)	H21A—C21—H21B	109.5
N1—C11—H11	107.1	S1—C21—H21C	109.5
C1—C11—H11	107.1	H21A—C21—H21C	109.5
C12—C11—H11	107.1	H21B—C21—H21C	109.5
C13—C12—C17	118.15 (17)

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁NOS
M_r	335.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.2753 (7), 14.9201 (13), 16.4212 (15)
β (°)	98.375 (1)
V (Å³)	1763.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.27 × 0.23 × 0.23

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.951, 0.959
No. of measured, independent and observed [I > 2/s(I)] reflections	20758, 3655, 2876
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.122, 1.05
No. of reflections	3655
No. of parameters	221
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.30

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 1997b).

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(±)-3-[2-(Methyl­sulfan­yl)eth­yl]-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine

Supporting information

Key indicators

checkCIF/PLATON results

(±)-3-[2-(Methylsulfanyl)ethyl]-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine