2′-Eth­oxy-1,3,3-trimethyl­spiro­[indoline-2,3′-3H-naphtho­[2,1-b][1,4]oxazine]

Lin, J.; Chai, W.; Yang, Y.; He, J.; Shu, K.

doi:10.1107/S1600536810022890

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1695

doi:10.1107/S1600536810022890

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2′-Ethoxy-1,3,3-trimethylspiro[indoline-2,3′-3H-naphtho[2,1-b][1,4]oxazine]

Jian Lin,^a Wenxiang Chai,^a ^* Yunyun Yang,^a Jiaojiao He ^a and Kangying Shu ^a

^aCollege of Materials Science and Engineering, China Jiliang University, Hangzhou 310018, People's Republic of China
^*Correspondence e-mail: wxchai_cm@yahoo.com.cn

(Received 2 June 2010; accepted 14 June 2010; online 18 June 2010)

In the title compound, C₂₄H₂₄N₂O₂, the five-membered ring of the indoline ring system adopts an envelope conformation with the spiro C atom at the flap. The dihedral angle between the benzene ring of the indoline ring system and the naphthalene ring system is 71.70 (7)°. In the crystal structure, pair of weak C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For applications of spirooxazines, see: Chibisov & Gardner (1999 ); Khairutdinov et al. (1998 ); Pozzo et al. (1993 ); Tan et al. (2005 ); Zhang et al. (2008 ). For related structures, see: Lin et al. (2009 ); Uznanski et al. (2001 ).

Experimental

Crystal data

C₂₄H₂₄N₂O₂
M_r = 372.45
Monoclinic, P 2₁ /c
a = 8.6105 (4) Å
b = 22.9239 (8) Å
c = 10.2022 (5) Å
β = 93.516 (4)°
V = 2009.98 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.34 × 0.30 × 0.20 mm

Data collection

Oxford Xcalibur Gemini ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.974, T_max = 0.984
12650 measured reflections
4449 independent reflections
2198 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.085
S = 0.98
4449 reflections
257 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O1ⁱ	0.93	2.60	3.5014 (18)	164
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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/S1600536810022890/is2559sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022890/is2559Isup2.hkl

checkCIF report

Comment top

Serve as an organic photochromic, spirooxazines have real or potential applications in many field, such as protection, decoration, display, memory, switches, photography, photometry and photomechanics (Chibisov & Gardner, 1999). For further approach to real applications, numerous types of spirooxazine derivatives have been reported over the past several decades (Pozzo et al., 1993; Khairutdinov et al., 1998; Zhang et al., 2008). Traditionally, synthesis of spirooxazines is based on a thermal condensation reaction of the corresponding alkylidene heterocycle or its conjugate acid with ortho-hydroxynitroso aromatic derivatives in most polar organic solvents. To be notice, alkylidene heterocycle, such as: 1,3,3-trimethyl-2- methyleneindoline derivatives, were not stable in the air at room temperature, so they must be purified by vacuum distillation before use (Tan et al., 2005). This brings to a big problem that we have to re-synthesis alkylidene heterocycle part if we want to get a novel spirooxazine with different substituents at alkylidene heterocycle moiety. According to our previous work (Lin et al., 2009) in which we reported a new strategy to get a 2'-position substituted spirooxazine, a new derivative, 1,3,3-trimethyl-2'-ethoxy-1,3-dihydrospiro(indole-2,3'-naphtho(2,1-b) (1,4)oxazine), (II), has been synthesized and its crystal structure is reported here.

Since we synthesized an unexpected new organic photochromic compound, (2S)-2'-ethoxy-1,3,3-trimethyl-6'-(piperidin-1-yl) spiro[indoline-2,3'-3'H-naphtho[2,1-b][1,4]oxazine], we studied on the possibility of the ethoxy reaction at the 2'-position of spirooxazine using another spirooxazine derivative, C₂₂H₂₀N₂O, (I). The title compound, C₂₄H₂₄N₂O₂, (II), was synthesized successfully (Fig. 1), which testified it is a general method to fabricate ethoxy-substituted (may be alkoxy-substituted) spirooxazines at the C2'carbon atom of the C2'=N1' bond.

The title compound, C₂₄H₂₄N₂O₂, consists of an ethoxy group bonded to parent molecule (I) at the 2'-position crystallizing with a molecule in the asymmetric unit (Fig. 2). The five-membered ring C1/N2/C6–C8 adopts an envelope conformation with the flap at C8. The dihedral angle between the benzene ring (atoms C1–C6) and the naphthalene ring (atoms C10–C19) is 71.70 (7)°. For the other 2'-position substituted derivatives (C₂₃H₂₂N₂O₂, C₂₇H₂₄N₂O₂ and C₂₉H₃₃N₃O₂), the corresponding dihedral angles are 74.2 (1), 76.5 (6) and 71.6 (2)/72.7 (2)°, respectively (Uznanski et al., 2001; Lin et al., 2009). The bond lengths and angles around the spiro carbon in (II) are similar to those in the other photochromic spirooxazines.

Related literature top

For applications of spirooxazines, see: Chibisov & Gardner (1999); Khairutdinov et al. (1998); Pozzo et al. (1993); Tan et al. (2005); Zhang et al. (2008). For related structures, see: Lin et al. (2009); Uznanski et al. (2001).

Experimental top

Potassium iodide (17 mg, 0.1 mmol) and the parent spirooxazine, 1,3,3-trimethylspiro[indoline-2,3'-[3H]-naphth[2,1-b][1,4]oxazine] (33 mg, 0.1 mmol) were heated in a Teflon-lined stainless steel autoclave with ethanol (10 ml) at 393 K. Block-shaped colorless crystals of (II), were obtained by slow evaporation from the filtrated reaction solution at room temperature. Yield: 45% (with reaction solution left). m.p.: 418–419 K. IR (KBr, cm^-1): 3053, 2982, 2964, 2888, 1724, 1714, 1637, 1609, 1577, 1508, 1490, 1466, 1398, 1383, 1367, 1321, 1296, 1267, 1252, 1232, 1198, 1188, 1153, 1140, 1101, 1086, 1037, 1024, 993, 977, 952, 895, 862, 816, 781, 750, 743, 683, 655, 632, 606, 566, 551, 516, 499, 437. ¹H NMR (CDCl₃): δ 6.56–8.47 (10H, ArH), 4.58 (2H, CH₂), 2.94 (3H, CH₃), 1.42 (3H, CH₃), 1.22 (6H, CH₃). Analysis found (calculated) for C₂₄H₂₄N₂O₂: C 77.35 (77.39), H 6.60 (6.49), N 7.50% (7.52%).

Computing details top

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO CCD (Oxford Diffraction, 2009); data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009); 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. Synthesis of the title compound, (II).
	Fig. 2. The structure of (II), showing the atom-labeling scheme of the asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 3. A packing diagram of (II), viewed along the a axis.

2'-Ethoxy-1,3,3-trimethylspiro[indoline-2,3'-3H- naphtho[2,1-b][1,4]oxazine] top

Crystal data top

C₂₄H₂₄N₂O₂	F(000) = 792
M_r = 372.45	D_x = 1.231 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 418 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.6105 (4) Å	Cell parameters from 3384 reflections
b = 22.9239 (8) Å	θ = 3.2–27.3°
c = 10.2022 (5) Å	µ = 0.08 mm⁻¹
β = 93.516 (4)°	T = 293 K
V = 2009.98 (15) Å³	Block, colorless
Z = 4	0.34 × 0.30 × 0.20 mm

Data collection top

Oxford Xcalibur Gemini ultra diffractometer	4449 independent reflections
Radiation source: fine-focus sealed tube	2198 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 10.3592 pixels mm^-1	θ_max = 27.3°, θ_min = 3.3°
ω scans	h = −11→10
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	k = −29→28
T_min = 0.974, T_max = 0.984	l = −13→13
12650 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.030P)²] where P = (F_o² + 2F_c²)/3
4449 reflections	(Δ/σ)_max < 0.001
257 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₄H₂₄N₂O₂	V = 2009.98 (15) Å³
M_r = 372.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.6105 (4) Å	µ = 0.08 mm⁻¹
b = 22.9239 (8) Å	T = 293 K
c = 10.2022 (5) Å	0.34 × 0.30 × 0.20 mm
β = 93.516 (4)°

Data collection top

Oxford Xcalibur Gemini ultra diffractometer	4449 independent reflections
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	2198 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.984	R_int = 0.033
12650 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 0.98	Δρ_max = 0.16 e Å⁻³
4449 reflections	Δρ_min = −0.18 e Å⁻³
257 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
O1	0.10563 (10)	0.53152 (4)	0.31415 (9)	0.0480 (3)
O2	0.22203 (12)	0.57809 (4)	0.00532 (9)	0.0593 (3)
N1	0.23974 (13)	0.48659 (5)	0.09366 (11)	0.0489 (3)
N2	0.09544 (13)	0.62319 (5)	0.21564 (12)	0.0482 (3)
C1	0.13539 (18)	0.66314 (6)	0.31558 (15)	0.0487 (4)
C2	0.0555 (2)	0.71249 (7)	0.3510 (2)	0.0713 (5)
H2	−0.0378	0.7234	0.3069	0.086*
C3	0.1210 (3)	0.74527 (7)	0.4557 (2)	0.0930 (7)
H3	0.0704	0.7789	0.4814	0.112*
C4	0.2579 (3)	0.72923 (9)	0.5217 (2)	0.0945 (7)
H4	0.2972	0.7511	0.5929	0.113*
C5	0.3369 (2)	0.68093 (7)	0.48276 (17)	0.0704 (5)
H5	0.4308	0.6704	0.5263	0.085*
C6	0.27635 (18)	0.64807 (6)	0.37867 (14)	0.0473 (4)
C7	0.34049 (16)	0.59543 (6)	0.31284 (14)	0.0450 (4)
C8	0.19045 (15)	0.57223 (5)	0.23417 (13)	0.0410 (3)
C9	0.21867 (16)	0.54118 (6)	0.10658 (13)	0.0454 (4)
C10	0.22059 (15)	0.45194 (5)	0.20565 (14)	0.0416 (3)
C11	0.26861 (15)	0.39259 (6)	0.20617 (15)	0.0441 (4)
C12	0.34693 (17)	0.36818 (6)	0.10200 (16)	0.0568 (4)
H12	0.3668	0.3910	0.0296	0.068*
C13	0.39369 (19)	0.31155 (7)	0.1063 (2)	0.0715 (5)
H13	0.4463	0.2961	0.0372	0.086*
C14	0.3635 (2)	0.27640 (7)	0.2132 (2)	0.0758 (6)
H14	0.3962	0.2377	0.2150	0.091*
C15	0.2869 (2)	0.29814 (6)	0.31467 (19)	0.0671 (5)
H15	0.2666	0.2741	0.3850	0.081*
C16	0.23744 (16)	0.35707 (6)	0.31460 (16)	0.0498 (4)
C17	0.16004 (19)	0.38141 (6)	0.41846 (16)	0.0620 (5)
H17	0.1372	0.3580	0.4891	0.074*
C18	0.11748 (17)	0.43869 (6)	0.41815 (15)	0.0575 (4)
H18	0.0670	0.4542	0.4883	0.069*
C19	0.15037 (16)	0.47384 (5)	0.31146 (14)	0.0438 (4)
C20	−0.06197 (19)	0.61855 (7)	0.15824 (19)	0.0748 (5)
H20A	−0.1290	0.6046	0.2232	0.112*
H20B	−0.0643	0.5918	0.0857	0.112*
H20C	−0.0971	0.6562	0.1277	0.112*
C21	0.46191 (17)	0.61472 (6)	0.21791 (16)	0.0620 (5)
H21A	0.4164	0.6429	0.1573	0.093*
H21B	0.4962	0.5815	0.1703	0.093*
H21C	0.5492	0.6319	0.2667	0.093*
C22	0.4158 (2)	0.55129 (6)	0.40929 (17)	0.0717 (5)
H22A	0.5025	0.5691	0.4574	0.108*
H22B	0.4513	0.5182	0.3618	0.108*
H22C	0.3408	0.5388	0.4693	0.108*
C23	0.2486 (2)	0.55342 (7)	−0.12201 (15)	0.0756 (5)
H23A	0.1723	0.5234	−0.1445	0.091*
H23B	0.3516	0.5362	−0.1213	0.091*
C24	0.2344 (2)	0.60208 (8)	−0.21924 (17)	0.0930 (6)
H24A	0.1314	0.6182	−0.2204	0.139*
H24B	0.2537	0.5875	−0.3050	0.139*
H24C	0.3090	0.6319	−0.1949	0.139*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0591 (6)	0.0358 (5)	0.0510 (6)	0.0043 (5)	0.0201 (5)	0.0047 (4)
O2	0.0940 (8)	0.0462 (6)	0.0382 (6)	−0.0067 (5)	0.0094 (5)	0.0066 (5)
N1	0.0654 (8)	0.0389 (7)	0.0436 (8)	−0.0023 (6)	0.0126 (6)	−0.0006 (6)
N2	0.0505 (8)	0.0390 (7)	0.0543 (8)	0.0086 (6)	−0.0031 (6)	0.0064 (6)
C1	0.0630 (10)	0.0305 (8)	0.0545 (10)	0.0000 (7)	0.0183 (8)	0.0056 (7)
C2	0.0823 (12)	0.0414 (10)	0.0938 (15)	0.0106 (9)	0.0344 (11)	0.0083 (10)
C3	0.1261 (19)	0.0404 (10)	0.1195 (19)	−0.0058 (12)	0.0634 (16)	−0.0214 (12)
C4	0.1252 (19)	0.0703 (14)	0.0921 (17)	−0.0293 (13)	0.0388 (15)	−0.0338 (12)
C5	0.0889 (13)	0.0617 (11)	0.0616 (12)	−0.0206 (10)	0.0123 (10)	−0.0123 (9)
C6	0.0604 (10)	0.0366 (8)	0.0458 (9)	−0.0056 (7)	0.0099 (8)	0.0008 (7)
C7	0.0509 (9)	0.0378 (8)	0.0460 (9)	0.0027 (7)	0.0004 (7)	0.0055 (7)
C8	0.0486 (9)	0.0349 (7)	0.0401 (9)	0.0017 (7)	0.0076 (7)	0.0061 (6)
C9	0.0567 (10)	0.0419 (9)	0.0381 (9)	−0.0045 (7)	0.0063 (7)	0.0043 (7)
C10	0.0487 (9)	0.0344 (8)	0.0426 (9)	−0.0033 (6)	0.0088 (7)	0.0003 (7)
C11	0.0401 (8)	0.0364 (8)	0.0557 (10)	−0.0027 (7)	0.0026 (7)	−0.0040 (7)
C12	0.0566 (10)	0.0454 (9)	0.0688 (12)	0.0018 (8)	0.0064 (9)	−0.0114 (8)
C13	0.0694 (12)	0.0547 (11)	0.0904 (15)	0.0075 (9)	0.0040 (10)	−0.0217 (10)
C14	0.0750 (13)	0.0415 (10)	0.1086 (18)	0.0119 (9)	−0.0133 (12)	−0.0127 (11)
C15	0.0749 (12)	0.0407 (9)	0.0841 (14)	−0.0019 (8)	−0.0092 (11)	0.0060 (9)
C16	0.0506 (10)	0.0356 (8)	0.0629 (11)	−0.0028 (7)	0.0004 (8)	0.0021 (8)
C17	0.0761 (12)	0.0466 (10)	0.0646 (12)	−0.0051 (8)	0.0152 (9)	0.0186 (8)
C18	0.0722 (11)	0.0476 (9)	0.0555 (11)	0.0025 (8)	0.0262 (8)	0.0082 (8)
C19	0.0493 (9)	0.0328 (8)	0.0503 (10)	0.0007 (7)	0.0117 (7)	0.0039 (7)
C20	0.0609 (12)	0.0686 (11)	0.0928 (14)	0.0078 (9)	−0.0135 (10)	0.0146 (10)
C21	0.0533 (10)	0.0603 (10)	0.0734 (12)	−0.0029 (8)	0.0120 (9)	−0.0050 (8)
C22	0.0805 (12)	0.0560 (10)	0.0748 (13)	0.0045 (9)	−0.0259 (10)	0.0107 (9)
C23	0.1160 (15)	0.0711 (11)	0.0406 (11)	−0.0154 (10)	0.0133 (10)	−0.0001 (9)
C24	0.1305 (17)	0.1011 (15)	0.0468 (12)	−0.0337 (13)	0.0011 (11)	0.0163 (10)

Geometric parameters (Å, º) top

O1—C19	1.3780 (14)	C12—C13	1.3591 (19)
O1—C8	1.4640 (15)	C12—H12	0.9300
O2—C9	1.3371 (15)	C13—C14	1.393 (2)
O2—C23	1.4478 (18)	C13—H13	0.9300
N1—C9	1.2724 (16)	C14—C15	1.356 (2)
N1—C10	1.4095 (16)	C14—H14	0.9300
N2—C1	1.3977 (18)	C15—C16	1.417 (2)
N2—C8	1.4320 (16)	C15—H15	0.9300
N2—C20	1.4471 (18)	C16—C17	1.402 (2)
C1—C6	1.3823 (19)	C17—C18	1.3631 (19)
C1—C2	1.383 (2)	C17—H17	0.9300
C2—C3	1.397 (3)	C18—C19	1.3971 (19)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.372 (3)	C20—H20A	0.9600
C3—H3	0.9300	C20—H20B	0.9600
C4—C5	1.371 (3)	C20—H20C	0.9600
C4—H4	0.9300	C21—H21A	0.9600
C5—C6	1.378 (2)	C21—H21B	0.9600
C5—H5	0.9300	C21—H21C	0.9600
C6—C7	1.5025 (19)	C22—H22A	0.9600
C7—C22	1.5278 (18)	C22—H22B	0.9600
C7—C21	1.5332 (19)	C22—H22C	0.9600
C7—C8	1.5713 (18)	C23—C24	1.493 (2)
C8—C9	1.5163 (18)	C23—H23A	0.9700
C10—C19	1.3649 (19)	C23—H23B	0.9700
C10—C11	1.4218 (17)	C24—H24A	0.9600
C11—C12	1.409 (2)	C24—H24B	0.9600
C11—C16	1.4125 (19)	C24—H24C	0.9600

C19—O1—C8	116.81 (10)	C14—C13—H13	119.7
C9—O2—C23	117.27 (11)	C15—C14—C13	120.53 (16)
C9—N1—C10	116.47 (12)	C15—C14—H14	119.7
C1—N2—C8	108.97 (11)	C13—C14—H14	119.7
C1—N2—C20	121.73 (13)	C14—C15—C16	120.68 (17)
C8—N2—C20	120.44 (11)	C14—C15—H15	119.7
C6—C1—C2	121.30 (15)	C16—C15—H15	119.7
C6—C1—N2	110.22 (12)	C17—C16—C11	118.98 (13)
C2—C1—N2	128.46 (15)	C17—C16—C15	122.42 (15)
C1—C2—C3	117.11 (17)	C11—C16—C15	118.60 (15)
C1—C2—H2	121.4	C18—C17—C16	121.46 (14)
C3—C2—H2	121.4	C18—C17—H17	119.3
C4—C3—C2	121.72 (18)	C16—C17—H17	119.3
C4—C3—H3	119.1	C17—C18—C19	119.34 (14)
C2—C3—H3	119.1	C17—C18—H18	120.3
C5—C4—C3	120.08 (19)	C19—C18—H18	120.3
C5—C4—H4	120.0	C10—C19—O1	120.43 (12)
C3—C4—H4	120.0	C10—C19—C18	121.66 (12)
C4—C5—C6	119.59 (18)	O1—C19—C18	117.88 (13)
C4—C5—H5	120.2	N2—C20—H20A	109.5
C6—C5—H5	120.2	N2—C20—H20B	109.5
C5—C6—C1	120.14 (15)	H20A—C20—H20B	109.5
C5—C6—C7	130.64 (15)	N2—C20—H20C	109.5
C1—C6—C7	109.21 (12)	H20A—C20—H20C	109.5
C6—C7—C22	113.40 (13)	H20B—C20—H20C	109.5
C6—C7—C21	109.53 (11)	C7—C21—H21A	109.5
C22—C7—C21	108.61 (12)	C7—C21—H21B	109.5
C6—C7—C8	100.77 (11)	H21A—C21—H21B	109.5
C22—C7—C8	114.07 (11)	C7—C21—H21C	109.5
C21—C7—C8	110.25 (12)	H21A—C21—H21C	109.5
N2—C8—O1	107.05 (10)	H21B—C21—H21C	109.5
N2—C8—C9	112.96 (11)	C7—C22—H22A	109.5
O1—C8—C9	106.91 (10)	C7—C22—H22B	109.5
N2—C8—C7	103.68 (10)	H22A—C22—H22B	109.5
O1—C8—C7	110.71 (10)	C7—C22—H22C	109.5
C9—C8—C7	115.30 (11)	H22A—C22—H22C	109.5
N1—C9—O2	122.16 (13)	H22B—C22—H22C	109.5
N1—C9—C8	125.60 (12)	O2—C23—C24	107.05 (14)
O2—C9—C8	112.23 (11)	O2—C23—H23A	110.3
C19—C10—N1	120.89 (12)	C24—C23—H23A	110.3
C19—C10—C11	119.45 (13)	O2—C23—H23B	110.3
N1—C10—C11	119.60 (13)	C24—C23—H23B	110.3
C12—C11—C16	118.97 (13)	H23A—C23—H23B	108.6
C12—C11—C10	121.99 (14)	C23—C24—H24A	109.5
C16—C11—C10	119.04 (13)	C23—C24—H24B	109.5
C13—C12—C11	120.65 (16)	H24A—C24—H24B	109.5
C13—C12—H12	119.7	C23—C24—H24C	109.5
C11—C12—H12	119.7	H24A—C24—H24C	109.5
C12—C13—C14	120.55 (17)	H24B—C24—H24C	109.5
C12—C13—H13	119.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1ⁱ	0.93	2.60	3.5014 (18)	164

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₄N₂O₂
M_r	372.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.6105 (4), 22.9239 (8), 10.2022 (5)
β (°)	93.516 (4)
V (Å³)	2009.98 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.34 × 0.30 × 0.20

Data collection
Diffractometer	Oxford Xcalibur Gemini ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)
T_min, T_max	0.974, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	12650, 4449, 2198
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.645

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.085, 0.98
No. of reflections	4449
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18

Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2009), CrysAlis PRO RED (Oxford Diffraction, 2009), 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
C18—H18···O1ⁱ	0.93	2.60	3.5014 (18)	164.0

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

The authors are grateful for financial support from the National Natural Science Foundation of China (project Nos. 50702054 and 20803070) and the Analysis and Testing Foundation of Zhejiang Province (project Nos. 2008 F70034 and 2008 F70053).

References

Chibisov, A. K. & Gardner, H. (1999). J. Phys. Chem. A, 103, 5211–5216. Web of Science CrossRef CAS Google Scholar
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Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
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Volume 66| Part 7| July 2010| Page o1695

doi:10.1107/S1600536810022890

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2′-Eth­­oxy-1,3,3-tri­methyl­spiro­[indoline-2,3′-3H-naphtho­[2,1-b][1,4]oxazine]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2′-Ethoxy-1,3,3-trimethylspiro[indoline-2,3′-3H-naphtho[2,1-b][1,4]oxazine]