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organic compounds
N-[2-(2-Methoxyphenyl)benzylidene]-tert-butylamine N-oxide
aLaboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, People's Republic of China, and bDepartment of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, People's Republic of China
*Correspondence e-mail: wyz@zju.edu.cn
In the molecule of the title compound, C18H21NO2, the two benzene rings are oriented at a dihedral angle of 58.19 (3)°. Intramolecular C—H⋯O hydrogen bonds result in the formation of one six- and one five-membered ring, which adopt twist and envelope conformations, respectively. In the C—H⋯O hydrogen bonds link the molecules.
Related literature
For general background, see: Hamburger & McCay (1989); Jotti et al. (1992
); Murphy et al. (2003
); Green et al. (2003
); Durand et al. (2007
); Hay et al. (2005
). For related literature, see: Fevig et al. (1996
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: PROCESS-AUTO (Rigaku, 1998); cell PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004
) and Larson (1970
); program(s) used to solve structure: SIR97 (Altomare et al., 1999
); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003
); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997
); software used to prepare material for publication: CrystalStructure.
Supporting information
10.1107/S1600536808014529/hk2462sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808014529/hk2462Isup2.hkl
For the preparation of the title compound, activated zinc powder (195.0 mg, 3.0 mmol) was added to a solution of 2-(2-methoxyphenyl)benzaldehyde (212.0 mg, 1.0 mmol) and 2-methyl-2-nitropropane (309.0 mg, 3.0 mmol) in ethanol (95%, 15 ml) at 283 K. Glacial acetic acid (0.35 ml, 6.0 mmol) was added dropwise to the resultant suspension in 1 h with stirring. After stirring at room temperature for 12 h, the reaction mixture was kept for another 48 h in a refrigerator. It was filtered to remove the solid materials and the filtrate was concentrated under reduced pressure. The residue was purified by δ: 9.43 (d, J = 8.8 Hz, 1H), 7.43-7.37 (m, 3H), 7.31 (s, 1H), 7.28-7.26 (m,1H), 7.17 (d, J = 6.4 Hz, 1H), 7.04 (t, J = 7.2 Hz, 1H), 6.98 (d, J = 8.0 Hz, 1H), 3.72 (s, 3H), 1.42 (s, 9H); 13 C NMR (100 MHz, CDCl3) δ: 156.2, 138.9, 131.5, 130.0, 129.5, 129.4, 129.2, 128.8 (2), 127.5, 127.4, 120.7 (2), 110.5, 70.6, 55.3, 28.0 (3); MS (ESI) m/z 284 (M + H). Anal. Calcd for C18H21NO2: C, 76.29; H, 7.47; N, 4.94. Found: C, 76.40; H, 7.45; N, 4.67. Single crystals of (I) suitable for X-ray analysis were grown in ethylacetate and hexane.
on silica gel with ethylacetate and hexane (1:3) as the to give the title compound (yield; 122.0 mg, 43%, m.p. 351-353 K). 1H NMR (400 MHz, CDCl3)H atoms were positioned geometrically, with C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell
PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004) and Larson (1970); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).C18H21NO2 | F(000) = 304.00 |
Mr = 283.37 | Dx = 1.152 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: P 2yb | Cell parameters from 4871 reflections |
a = 10.2526 (15) Å | θ = 3.2–27.4° |
b = 8.5576 (13) Å | µ = 0.08 mm−1 |
c = 10.3333 (16) Å | T = 296 K |
β = 115.742 (3)° | Platelet, colorless |
V = 816.6 (2) Å3 | 0.30 × 0.28 × 0.09 mm |
Z = 2 |
Rigaku R-AXIS RAPID-S diffractometer | 967 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.035 |
ω scans | θmax = 27.4° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −13→13 |
Tmin = 0.968, Tmax = 0.993 | k = −11→10 |
7869 measured reflections | l = −13→13 |
1981 independent reflections |
Refinement on F2 | w = 1/[1.0600σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.034 | (Δ/σ)max < 0.001 |
wR(F2) = 0.058 | Δρmax = 0.23 e Å−3 |
S = 1.00 | Δρmin = −0.21 e Å−3 |
1981 reflections | Extinction correction: Larson (1970) |
191 parameters | Extinction coefficient: 287 (12) |
H-atom parameters constrained |
C18H21NO2 | V = 816.6 (2) Å3 |
Mr = 283.37 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 10.2526 (15) Å | µ = 0.08 mm−1 |
b = 8.5576 (13) Å | T = 296 K |
c = 10.3333 (16) Å | 0.30 × 0.28 × 0.09 mm |
β = 115.742 (3)° |
Rigaku R-AXIS RAPID-S diffractometer | 1981 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 967 reflections with F2 > 2σ(F2) |
Tmin = 0.968, Tmax = 0.993 | Rint = 0.035 |
7869 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 191 parameters |
wR(F2) = 0.058 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.23 e Å−3 |
1981 reflections | Δρmin = −0.21 e Å−3 |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.9021 (2) | 0.3664 (2) | 0.8067 (2) | 0.1211 (8) | |
O2 | 0.89199 (16) | 0.2119 (2) | 0.40803 (18) | 0.0749 (6) | |
N1 | 0.8516 (2) | 0.2377 (2) | 0.7378 (2) | 0.0699 (7) | |
C1 | 0.7579 (2) | 0.2359 (3) | 0.6043 (2) | 0.0539 (7) | |
C2 | 0.6914 (2) | 0.3714 (3) | 0.5161 (2) | 0.0519 (7) | |
C3 | 0.6741 (2) | 0.5115 (3) | 0.5752 (2) | 0.0657 (9) | |
C4 | 0.6018 (2) | 0.6370 (3) | 0.4891 (3) | 0.0749 (9) | |
C5 | 0.5479 (2) | 0.6233 (3) | 0.3431 (3) | 0.0794 (10) | |
C6 | 0.5634 (2) | 0.4858 (3) | 0.2821 (2) | 0.0706 (9) | |
C7 | 0.6339 (2) | 0.3570 (3) | 0.3658 (2) | 0.0552 (8) | |
C8 | 0.6389 (2) | 0.2103 (3) | 0.2930 (2) | 0.0569 (8) | |
C9 | 0.5111 (2) | 0.1408 (3) | 0.1954 (2) | 0.0729 (9) | |
C10 | 0.5107 (3) | 0.0054 (4) | 0.1245 (2) | 0.0890 (11) | |
C11 | 0.6400 (3) | −0.0637 (3) | 0.1491 (2) | 0.0910 (11) | |
C12 | 0.7694 (3) | 0.0020 (3) | 0.2437 (2) | 0.0775 (10) | |
C13 | 0.7690 (2) | 0.1373 (3) | 0.3151 (2) | 0.0644 (9) | |
C14 | 1.0274 (2) | 0.1362 (3) | 0.4454 (3) | 0.0978 (11) | |
C15 | 0.9129 (2) | 0.0920 (3) | 0.8265 (2) | 0.0704 (9) | |
C16 | 0.8509 (3) | −0.0534 (3) | 0.7407 (3) | 0.1022 (12) | |
C17 | 1.0746 (2) | 0.0986 (4) | 0.8838 (3) | 0.1160 (12) | |
C18 | 0.8694 (2) | 0.1013 (4) | 0.9492 (2) | 0.1048 (11) | |
H1 | 0.7307 | 0.1385 | 0.5610 | 0.065* | |
H3 | 0.7118 | 0.5211 | 0.6745 | 0.079* | |
H4 | 0.5900 | 0.7294 | 0.5302 | 0.090* | |
H5 | 0.5004 | 0.7074 | 0.2847 | 0.095* | |
H6 | 0.5260 | 0.4787 | 0.1826 | 0.085* | |
H9 | 0.4232 | 0.1878 | 0.1778 | 0.087* | |
H10 | 0.4238 | −0.0390 | 0.0605 | 0.107* | |
H11 | 0.6405 | −0.1558 | 0.1016 | 0.109* | |
H12 | 0.8566 | −0.0452 | 0.2591 | 0.093* | |
H141 | 1.0270 | 0.0361 | 0.4873 | 0.117* | |
H142 | 1.0425 | 0.1222 | 0.3608 | 0.117* | |
H143 | 1.1040 | 0.1992 | 0.5135 | 0.117* | |
H161 | 0.8724 | −0.0552 | 0.6590 | 0.123* | |
H162 | 0.7479 | −0.0546 | 0.7085 | 0.123* | |
H163 | 0.8929 | −0.1435 | 0.7995 | 0.123* | |
H171 | 1.1086 | 0.1991 | 0.9263 | 0.139* | |
H172 | 1.1173 | 0.0187 | 0.9550 | 0.139* | |
H173 | 1.1015 | 0.0822 | 0.8066 | 0.139* | |
H181 | 0.8892 | 0.0033 | 0.9993 | 0.126* | |
H182 | 0.7678 | 0.1240 | 0.9117 | 0.126* | |
H183 | 0.9237 | 0.1827 | 1.0144 | 0.126* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1395 (18) | 0.0722 (15) | 0.0812 (15) | −0.0167 (15) | −0.0179 (12) | −0.0059 (13) |
O2 | 0.0562 (9) | 0.0805 (13) | 0.0934 (13) | 0.0110 (10) | 0.0374 (8) | −0.0032 (12) |
N1 | 0.0728 (13) | 0.0637 (16) | 0.0555 (14) | −0.0094 (14) | 0.0113 (11) | −0.0029 (14) |
C1 | 0.0509 (11) | 0.0599 (18) | 0.0493 (15) | −0.0037 (15) | 0.0203 (11) | −0.0017 (15) |
C2 | 0.0405 (12) | 0.0608 (18) | 0.0561 (16) | −0.0024 (12) | 0.0227 (11) | −0.0011 (15) |
C3 | 0.0477 (14) | 0.078 (2) | 0.0703 (19) | −0.0052 (14) | 0.0250 (13) | −0.0124 (18) |
C4 | 0.0504 (14) | 0.068 (2) | 0.103 (2) | 0.0064 (15) | 0.0308 (14) | −0.0027 (19) |
C5 | 0.0627 (16) | 0.076 (2) | 0.097 (2) | 0.0188 (17) | 0.0328 (16) | 0.021 (2) |
C6 | 0.0618 (16) | 0.082 (2) | 0.069 (2) | 0.0091 (15) | 0.0299 (14) | 0.0130 (19) |
C7 | 0.0431 (13) | 0.0695 (19) | 0.0572 (17) | 0.0068 (14) | 0.0257 (11) | 0.0083 (17) |
C8 | 0.0621 (14) | 0.0682 (19) | 0.0450 (14) | 0.0043 (16) | 0.0274 (12) | 0.0012 (15) |
C9 | 0.0699 (17) | 0.094 (2) | 0.0497 (16) | 0.0017 (16) | 0.0212 (13) | −0.0003 (17) |
C10 | 0.102 (2) | 0.103 (2) | 0.0586 (19) | −0.015 (2) | 0.0314 (17) | −0.012 (2) |
C11 | 0.126 (2) | 0.086 (2) | 0.067 (2) | −0.004 (2) | 0.0474 (19) | −0.0130 (18) |
C12 | 0.097 (2) | 0.078 (2) | 0.069 (2) | 0.0104 (17) | 0.0472 (17) | 0.0009 (18) |
C13 | 0.0699 (16) | 0.075 (2) | 0.0579 (17) | 0.0022 (16) | 0.0366 (13) | 0.0008 (16) |
C14 | 0.0666 (15) | 0.105 (2) | 0.130 (2) | 0.0198 (18) | 0.0496 (15) | 0.008 (2) |
C15 | 0.0706 (17) | 0.069 (2) | 0.0573 (18) | −0.0000 (17) | 0.0146 (13) | 0.0103 (17) |
C16 | 0.129 (2) | 0.066 (2) | 0.087 (2) | 0.008 (2) | 0.0230 (19) | 0.0098 (19) |
C17 | 0.0771 (17) | 0.121 (2) | 0.124 (2) | 0.003 (2) | 0.0196 (16) | 0.033 (2) |
C18 | 0.113 (2) | 0.120 (2) | 0.0668 (19) | 0.010 (2) | 0.0254 (17) | 0.025 (2) |
O1—N1 | 1.291 (3) | C1—H1 | 0.930 |
O2—C13 | 1.366 (2) | C3—H3 | 0.930 |
O2—C14 | 1.425 (3) | C4—H4 | 0.930 |
N1—C1 | 1.293 (2) | C5—H5 | 0.930 |
N1—C15 | 1.514 (3) | C6—H6 | 0.930 |
C1—C2 | 1.450 (3) | C9—H9 | 0.930 |
C2—C3 | 1.391 (4) | C10—H10 | 0.930 |
C2—C7 | 1.407 (3) | C11—H11 | 0.930 |
C3—C4 | 1.386 (3) | C12—H12 | 0.930 |
C4—C5 | 1.368 (4) | C14—H141 | 0.960 |
C5—C6 | 1.376 (4) | C14—H142 | 0.960 |
C6—C7 | 1.394 (3) | C14—H143 | 0.960 |
C7—C8 | 1.476 (3) | C16—H161 | 0.960 |
C8—C9 | 1.393 (3) | C16—H162 | 0.960 |
C8—C13 | 1.399 (3) | C16—H163 | 0.960 |
C9—C10 | 1.370 (4) | C17—H171 | 0.960 |
C10—C11 | 1.371 (5) | C17—H172 | 0.960 |
C11—C12 | 1.381 (3) | C17—H173 | 0.960 |
C12—C13 | 1.373 (4) | C18—H181 | 0.960 |
C15—C16 | 1.499 (3) | C18—H182 | 0.960 |
C15—C17 | 1.500 (3) | C18—H183 | 0.960 |
C15—C18 | 1.518 (4) | ||
C13—O2—C14 | 118.1 (2) | C4—C5—H5 | 119.8 |
O1—N1—C1 | 122.2 (2) | C6—C5—H5 | 119.8 |
O1—N1—C15 | 114.02 (18) | C5—C6—H6 | 119.2 |
C1—N1—C15 | 123.8 (2) | C7—C6—H6 | 119.2 |
N1—C1—C2 | 126.1 (2) | C8—C9—H9 | 118.9 |
C1—C2—C3 | 121.9 (2) | C10—C9—H9 | 118.9 |
C1—C2—C7 | 118.8 (2) | C9—C10—H10 | 120.4 |
C3—C2—C7 | 119.2 (2) | C11—C10—H10 | 120.4 |
C2—C3—C4 | 121.4 (2) | C10—C11—H11 | 119.7 |
C3—C4—C5 | 119.2 (2) | C12—C11—H11 | 119.7 |
C4—C5—C6 | 120.5 (2) | C11—C12—H12 | 120.1 |
C5—C6—C7 | 121.6 (2) | C13—C12—H12 | 120.1 |
C2—C7—C6 | 118.1 (2) | O2—C14—H141 | 109.5 |
C2—C7—C8 | 123.1 (2) | O2—C14—H142 | 109.5 |
C6—C7—C8 | 118.7 (2) | O2—C14—H143 | 109.5 |
C7—C8—C9 | 120.2 (2) | H141—C14—H142 | 109.5 |
C7—C8—C13 | 122.56 (19) | H141—C14—H143 | 109.5 |
C9—C8—C13 | 117.3 (2) | H142—C14—H143 | 109.5 |
C8—C9—C10 | 122.1 (2) | C15—C16—H161 | 109.5 |
C9—C10—C11 | 119.2 (2) | C15—C16—H162 | 109.5 |
C10—C11—C12 | 120.7 (3) | C15—C16—H163 | 109.5 |
C11—C12—C13 | 119.9 (3) | H161—C16—H162 | 109.5 |
O2—C13—C8 | 115.4 (2) | H161—C16—H163 | 109.5 |
O2—C13—C12 | 123.7 (2) | H162—C16—H163 | 109.5 |
C8—C13—C12 | 120.9 (2) | C15—C17—H171 | 109.5 |
N1—C15—C16 | 111.56 (19) | C15—C17—H172 | 109.5 |
N1—C15—C17 | 107.7 (2) | C15—C17—H173 | 109.5 |
N1—C15—C18 | 105.5 (2) | H171—C17—H172 | 109.5 |
C16—C15—C17 | 112.1 (2) | H171—C17—H173 | 109.5 |
C16—C15—C18 | 109.6 (2) | H172—C17—H173 | 109.5 |
C17—C15—C18 | 110.1 (2) | C15—C18—H181 | 109.5 |
N1—C1—H1 | 116.9 | C15—C18—H182 | 109.5 |
C2—C1—H1 | 116.9 | C15—C18—H183 | 109.5 |
C2—C3—H3 | 119.3 | H181—C18—H182 | 109.5 |
C4—C3—H3 | 119.3 | H181—C18—H183 | 109.5 |
C3—C4—H4 | 120.4 | H182—C18—H183 | 109.5 |
C5—C4—H4 | 120.4 | ||
C14—O2—C13—C8 | 174.2 (2) | C3—C4—C5—C6 | 0.9 (4) |
C14—O2—C13—C12 | −7.4 (4) | C4—C5—C6—C7 | −0.1 (3) |
O1—N1—C1—C2 | −3.3 (4) | C5—C6—C7—C2 | −0.9 (4) |
O1—N1—C15—C16 | −179.7 (2) | C5—C6—C7—C8 | 176.3 (2) |
O1—N1—C15—C17 | −56.2 (3) | C2—C7—C8—C9 | 121.0 (2) |
O1—N1—C15—C18 | 61.4 (2) | C2—C7—C8—C13 | −60.5 (4) |
C1—N1—C15—C16 | −0.3 (4) | C6—C7—C8—C9 | −56.0 (3) |
C1—N1—C15—C17 | 123.2 (2) | C6—C7—C8—C13 | 122.5 (2) |
C1—N1—C15—C18 | −119.2 (2) | C7—C8—C9—C10 | 179.5 (2) |
C15—N1—C1—C2 | 177.4 (2) | C7—C8—C13—O2 | −0.6 (4) |
N1—C1—C2—C3 | −26.8 (4) | C7—C8—C13—C12 | −179.0 (2) |
N1—C1—C2—C7 | 157.7 (2) | C9—C8—C13—O2 | 178.0 (2) |
C1—C2—C3—C4 | −175.7 (2) | C9—C8—C13—C12 | −0.5 (4) |
C1—C2—C7—C6 | 176.6 (2) | C13—C8—C9—C10 | 0.9 (4) |
C1—C2—C7—C8 | −0.5 (3) | C8—C9—C10—C11 | −0.5 (5) |
C3—C2—C7—C6 | 1.0 (3) | C9—C10—C11—C12 | −0.2 (4) |
C3—C2—C7—C8 | −176.1 (2) | C10—C11—C12—C13 | 0.6 (5) |
C7—C2—C3—C4 | −0.2 (3) | C11—C12—C13—O2 | −178.5 (2) |
C2—C3—C4—C5 | −0.8 (4) | C11—C12—C13—C8 | −0.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1 | 0.93 | 2.26 | 2.806 (3) | 117 |
C17—H171···O1 | 0.96 | 2.41 | 2.791 (3) | 104 |
C18—H181···O1i | 0.96 | 2.50 | 3.280 (3) | 139 |
Symmetry code: (i) −x+2, y−1/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C18H21NO2 |
Mr | 283.37 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 296 |
a, b, c (Å) | 10.2526 (15), 8.5576 (13), 10.3333 (16) |
β (°) | 115.742 (3) |
V (Å3) | 816.6 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.28 × 0.09 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID-S diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.968, 0.993 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 7869, 1981, 967 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.058, 1.00 |
No. of reflections | 1981 |
No. of parameters | 191 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.21 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004) and Larson (1970), SIR97 (Altomare et al., 1999), CRYSTALS (Betteridge et al., 2003), ORTEP-3 for Windows (Farrugia, 1997), CrystalStructure (Rigaku/MSC, 2004).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1 | 0.93 | 2.26 | 2.806 (3) | 117.00 |
C17—H171···O1 | 0.96 | 2.41 | 2.791 (3) | 104.00 |
C18—H181···O1i | 0.96 | 2.50 | 3.280 (3) | 139.00 |
Symmetry code: (i) −x+2, y−1/2, −z+2. |
Acknowledgements
This work is supported by a research grant from the Natural Science Foundation of Zhejiang Province in China (grant No. Y207295). Mr Jianming Gu and Xiurong Hu of the X-ray crystallography facility of Zhejiang University are acknowledged for their assistance with the crystal structural analysis.
References
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N-tert-Butyl-α-phenylnitrone (PBN) and its derivatives have been widely used as spin trapping agents in biology for detecting active free radicals such as oxygen- and carbon-centered radicals (Hamburger & McCay, 1989; Jotti et al., 1992; Murphy et al., 2003) and as antioxidant for treating age-related diseases (Green et al., 2003). The amphiphilic spin traps have been developed for potential use as therapeutic antioxidants (Durand et al., 2007), while the lipophilic spin traps are targeted for interception of radicals within non-aqueous phases and detection of radicals in complex biphasic biological systems (Hay et al., 2005). To explore the effect of the substituent attached to the benzene ring of PBN on the spin trapping ability, we have designed and synthesized a number of novel lipophilic spin traps derived from PBN, to which an additional aromatic group is attached.
In the molecule of (I), (Fig. 1), rings A (C2-C7) and B (C8-C13) are, of course, planar, and they are oriented at a dihedral angle of 58.19 (3)°. Unlike the N-tert-Butyl-α-phenylnitrone (Fevig et al., 1996), atoms C1, N1 and O1 is not coplanar with ring A. Intramolecular C-H···O hydrogen bonds result in the formation of one six- and one five-membered rings C (C1-C3/O1/N1/H3) and D (O1/N1/C15/C17/H171). Ring C adopts twisted conformation having total puckering amplitude, QT, of 0.443 (3) Å, while ring D has envelope conformation, with C15 atom displaced by -0.663 (3) Å from the plane of the other ring atoms.
In the crystal structure, intermolecular C-H···O hydrogen bonds link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.