2-(2-Hy­droxy­phen­yl)-3,4-dihydro­iso­quinolin-1(2H)-one

Yang, J.; Ma, Y.; Pan, M.; Cao, F.; Zhou, L.

doi:10.1107/S160053681103710X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2721

https://doi.org/10.1107/S160053681103710X

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2-(2-Hydroxyphenyl)-3,4-dihydroisoquinolin-1(2H)-one

Jian Yang,^a Yanni Ma,^a Meng Pan,^a Fangjun Cao ^a and Le Zhou ^a ^*

^aCollege of Science, Northwest Agriculture and Forest University, Yangling 712100, People's Republic of China
^*Correspondence e-mail: zhoulechem@yahoo.com.cn

(Received 31 August 2011; accepted 13 September 2011; online 30 September 2011)

There are two independent molecules in the asymmetric unit of the title compound, C₁₅H₁₃NO₂, in both the six-membered dihydropyridine rings adopt a half-chair conformation. The two benzene rings make dihedral angles of 43.66 (10) and 62.22 (10)° in the two molecules. In the crystal, the two independent molecules are linked alternately by intermolecular O—H⋯O hydrogen bonds, forming a zigzag chain along the c axis. Furthermore, intermolecular C—H⋯π interactions link the chains into a three-dimensional network.

Related literature

For the synthesis of the title compound, see: Shaw & Zhang (2008 ). For the bioactivity of tetrahydroisoquinoline derivatives, see: Kamal et al. (2011 ); Liu et al. (2009 ); Vrba et al. (2009 ); Abe et al. (2005 ); Adhami et al. (2004 ); Storch et al. (2002 ).

Experimental

Crystal data

C₁₅H₁₃NO₂
M_r = 239.26
Monoclinic, C 2/c
a = 21.350 (3) Å
b = 11.0670 (14) Å
c = 21.064 (3) Å
β = 100.227 (2)°
V = 4897.9 (11) Å³
Z = 16
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.50 × 0.35 × 0.34 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.958, T_max = 0.971
17755 measured reflections
4559 independent reflections
2998 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.120
S = 1.01
4559 reflections
326 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3ⁱ	0.82	1.84	2.6388 (18)	166
O4—H4A⋯O1	0.82	1.85	2.6668 (17)	175
C7—H7B⋯Cg2ⁱⁱ	0.97	2.92	3.770 (2)	147
C19—H19⋯Cg2ⁱⁱⁱ	0.93	2.78	3.518 (3)	137
C23—H23A⋯Cg3^iv	0.97	2.87	3.771 (2)	155
Symmetry codes: (i) $[x, -y+2, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y+{\script{5\over 2}}, -z+2]$ ; (iii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iv) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z+2]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 global, I. DOI: https://doi.org/10.1107/S160053681103710X/is2770sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681103710X/is2770Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681103710X/is2770Isup3.cml

checkCIF report

Comment top

The tetrahydroisoquinoline derivatives have recently attracted a great deal of attention because of their outstanding bioactivity, such as neurotoxicity (Abe et al., 2005; Storch et al., 2002), antitumor activity (Vrba et al., 2009; Adhami et al., 2004), antimicrobial activity (Kamal et al., 2011; Liu et al., 2009), and so on. With the interests in the synthesis of tetrahydroisoquinoline derivatives with bioactivity, we herein report the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound include two independent molecules (Fig. 1), each is built up from one 3,4-dihydroisoquinolin-1(2H)-one fragment connected to one 2-hydroxybenzene ring through the C—N bond. Benzene rings C1—C6 and C10—C15 are inclined with respect to one another with a dihedral angle of 43.66 (10) °, and benzene C16—C21 and C25—C30 with a dihedral angle of 62.22 (10) °. The conformation of the six-membered heterocycle of 3,4-dihydroisoquinolin-1(2H)-one fragment is analyzed with respect to the plane formed by C1/C6/C7/C9 and the corresponding deviations of the atoms C8 and N1 are 0.852 and 0.339 Å, respectively. Meanwhile, the corresponding deviations of the atoms C23 and N2 from the plane formed by C16/C21/C22/C24 are 0.761 and 0.289 Å, respectively.

In the crystal structure, the molecules are linked by intermolecular O—H···O hydrogen bonds (Table 1) into a chain along the c axis. These chains are further connected by C—H···π interactions (C7—H7B···Cg2 and C23—H23A···Cg3; Table 1) into a sheet, where Cg2 is the centroid of the benzene C1—C6 ring and Cg3 is of the benzene C10—C15 ring. Furthermore, C19—H19···Cg2 interaction connects the sheets into three-dimension framework (Fig. 2).

Related literature top

For the synthesis of the title compound, see: Shaw & Zhang (2008). For the bioactivity of tetrahydroisoquinoline derivatives, see: Kamal et al. (2011); Liu et al. (2009); Vrba et al. (2009); Abe et al. (2005); Adhami et al. (2004); Storch et al. (2002).

Experimental top

The title compound was synthesized according to the literature procedure (Shaw & Zhang, 2008). An NaOH solution (0.1 mol/L, 10 ml) was added to the solution of 2-(2-hydroxyphenyl)-3,4-dihydroisoquinolinum bromide (304 mg, 1 mmol) in ethanol (10 ml) dropwise under stirring. After 24 h, the mixture was extracted by chloroform (30 ml), dried over anhydrous Na₂SO₄ and evaporated under reduced pressure. Further purification by silicagel column chromatography (petroleum ether / ethyl acetate = 5:1) and recrystallization gave 85 mg the title compound (yield 36%; m.p. 433–434 K).

Structure description top

For the synthesis of the title compound, see: Shaw & Zhang (2008). For the bioactivity of tetrahydroisoquinoline derivatives, see: Kamal et al. (2011); Liu et al. (2009); Vrba et al. (2009); Abe et al. (2005); Adhami et al. (2004); Storch et al. (2002).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. The asymmetric unit of the title compound with 30% probability displacement ellipsoids.
	Fig. 2. A partial packing diagram of the title compound. Dashed lines indicate the hydrogen bonds and C—H···π interactions.

2-(2-Hydroxyphenyl)-3,4-dihydroisoquinolin-1(2H)-one top

Crystal data top

C₁₅H₁₃NO₂	F(000) = 2016
M_r = 239.26	D_x = 1.298 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3281 reflections
a = 21.350 (3) Å	θ = 2.5–22.2°
b = 11.0670 (14) Å	µ = 0.09 mm⁻¹
c = 21.064 (3) Å	T = 296 K
β = 100.227 (2)°	Block, colourless
V = 4897.9 (11) Å³	0.50 × 0.35 × 0.34 mm
Z = 16

Data collection top

Bruker APEXII CCD area-detector diffractometer	4559 independent reflections
Radiation source: fine-focus sealed tube	2998 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→25
T_min = 0.958, T_max = 0.971	k = −13→13
17755 measured reflections	l = −25→25

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0584P)² + 1.0944P] where P = (F_o² + 2F_c²)/3
4559 reflections	(Δ/σ)_max = 0.001
326 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₅H₁₃NO₂	V = 4897.9 (11) Å³
M_r = 239.26	Z = 16
Monoclinic, C2/c	Mo Kα radiation
a = 21.350 (3) Å	µ = 0.09 mm⁻¹
b = 11.0670 (14) Å	T = 296 K
c = 21.064 (3) Å	0.50 × 0.35 × 0.34 mm
β = 100.227 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4559 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2998 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.971	R_int = 0.034
17755 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.01	Δρ_max = 0.19 e Å⁻³
4559 reflections	Δρ_min = −0.16 e Å⁻³
326 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
C1	0.64702 (8)	1.22521 (16)	0.96814 (8)	0.0475 (4)
C2	0.64055 (9)	1.20334 (19)	0.90234 (9)	0.0557 (5)
H2	0.6244	1.1297	0.8855	0.067*
C3	0.65796 (10)	1.2900 (2)	0.86179 (10)	0.0669 (6)
H3	0.6529	1.2752	0.8177	0.080*
C4	0.68274 (10)	1.3979 (2)	0.88650 (12)	0.0726 (6)
H4	0.6942	1.4566	0.8591	0.087*
C5	0.69074 (10)	1.41978 (19)	0.95193 (12)	0.0665 (6)
H5	0.7086	1.4924	0.9684	0.080*
C6	0.67252 (8)	1.33481 (17)	0.99346 (9)	0.0529 (5)
C7	0.67903 (10)	1.35321 (18)	1.06454 (10)	0.0646 (6)
H7A	0.6800	1.4390	1.0741	0.077*
H7B	0.7186	1.3178	1.0863	0.077*
C8	0.62387 (10)	1.29515 (17)	1.08845 (9)	0.0599 (5)
H8A	0.6301	1.3014	1.1351	0.072*
H8B	0.5849	1.3373	1.0707	0.072*
C9	0.62857 (8)	1.13100 (17)	1.01102 (8)	0.0463 (4)
C10	0.60218 (8)	1.08107 (17)	1.11477 (8)	0.0490 (4)
C11	0.64429 (8)	1.06340 (17)	1.17237 (8)	0.0501 (5)
C12	0.62941 (10)	0.9830 (2)	1.21757 (9)	0.0626 (5)
H12	0.6573	0.9722	1.2564	0.075*
C13	0.57360 (11)	0.9192 (2)	1.20525 (11)	0.0732 (6)
H13	0.5637	0.8650	1.2358	0.088*
C14	0.53190 (10)	0.9349 (2)	1.14774 (12)	0.0763 (7)
H14	0.4943	0.8906	1.1394	0.092*
C15	0.54588 (9)	1.0160 (2)	1.10293 (10)	0.0630 (5)
H15	0.5174	1.0273	1.0645	0.076*
C16	0.87970 (8)	0.86788 (16)	0.85716 (8)	0.0486 (4)
C17	0.91880 (9)	0.92042 (19)	0.81889 (10)	0.0631 (5)
H17	0.9022	0.9415	0.7765	0.076*
C18	0.98214 (10)	0.9416 (2)	0.84322 (12)	0.0776 (7)
H18	1.0083	0.9763	0.8173	0.093*
C19	1.00639 (11)	0.9113 (2)	0.90587 (13)	0.0839 (7)
H19	1.0489	0.9268	0.9227	0.101*
C20	0.96817 (11)	0.8582 (2)	0.94387 (11)	0.0792 (7)
H20	0.9853	0.8378	0.9862	0.095*
C21	0.90435 (9)	0.83423 (18)	0.92027 (9)	0.0570 (5)
C22	0.86093 (10)	0.7762 (2)	0.95990 (9)	0.0669 (6)
H22A	0.8428	0.8378	0.9839	0.080*
H22B	0.8852	0.7210	0.9906	0.080*
C23	0.80834 (10)	0.70835 (19)	0.91819 (9)	0.0610 (5)
H23A	0.8255	0.6360	0.9017	0.073*
H23B	0.7771	0.6837	0.9439	0.073*
C24	0.81068 (9)	0.85581 (16)	0.83172 (8)	0.0477 (4)
C25	0.70918 (8)	0.77602 (15)	0.84686 (8)	0.0458 (4)
C26	0.67305 (8)	0.84301 (15)	0.88288 (8)	0.0445 (4)
C27	0.60732 (9)	0.83775 (18)	0.86810 (9)	0.0555 (5)
H27	0.5829	0.8822	0.8922	0.067*
C28	0.57827 (10)	0.7672 (2)	0.81807 (10)	0.0678 (6)
H28	0.5341	0.7645	0.8082	0.081*
C29	0.61354 (11)	0.7005 (2)	0.78239 (10)	0.0713 (6)
H29	0.5933	0.6528	0.7485	0.086*
C30	0.67912 (10)	0.70412 (18)	0.79681 (9)	0.0613 (5)
H30	0.7031	0.6583	0.7729	0.074*
N1	0.61817 (7)	1.16666 (13)	1.06934 (7)	0.0495 (4)
N2	0.77725 (7)	0.78299 (13)	0.86388 (7)	0.0482 (4)
O1	0.62296 (6)	1.02339 (11)	0.99405 (6)	0.0565 (3)
O2	0.69906 (6)	1.12681 (14)	1.18018 (6)	0.0672 (4)
H2A	0.7209	1.1098	1.2151	0.101*
O3	0.78604 (6)	0.91442 (13)	0.78357 (6)	0.0650 (4)
O4	0.70448 (6)	0.91102 (12)	0.93171 (6)	0.0584 (4)
H4A	0.6787	0.9484	0.9488	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0401 (10)	0.0511 (11)	0.0487 (10)	0.0066 (8)	0.0008 (8)	−0.0025 (9)
C2	0.0509 (11)	0.0617 (12)	0.0527 (11)	0.0019 (9)	0.0040 (9)	−0.0010 (10)
C3	0.0659 (14)	0.0788 (15)	0.0570 (12)	0.0069 (12)	0.0133 (10)	0.0084 (11)
C4	0.0673 (14)	0.0702 (15)	0.0847 (17)	0.0048 (12)	0.0252 (12)	0.0157 (13)
C5	0.0536 (12)	0.0548 (12)	0.0909 (17)	−0.0009 (10)	0.0122 (11)	0.0018 (12)
C6	0.0422 (10)	0.0517 (11)	0.0620 (12)	0.0061 (9)	0.0014 (8)	−0.0054 (10)
C7	0.0681 (13)	0.0524 (12)	0.0678 (13)	−0.0005 (10)	−0.0025 (10)	−0.0135 (10)
C8	0.0706 (13)	0.0551 (12)	0.0510 (11)	0.0115 (10)	0.0029 (9)	−0.0133 (9)
C9	0.0409 (10)	0.0511 (11)	0.0437 (10)	0.0058 (8)	−0.0008 (8)	−0.0085 (9)
C10	0.0434 (10)	0.0593 (11)	0.0445 (10)	0.0055 (9)	0.0084 (8)	−0.0114 (9)
C11	0.0420 (10)	0.0637 (12)	0.0445 (10)	0.0013 (9)	0.0078 (8)	−0.0092 (9)
C12	0.0604 (13)	0.0782 (14)	0.0496 (11)	0.0048 (11)	0.0110 (9)	−0.0009 (10)
C13	0.0717 (15)	0.0833 (16)	0.0704 (15)	−0.0019 (13)	0.0285 (12)	0.0020 (12)
C14	0.0559 (13)	0.0919 (17)	0.0847 (17)	−0.0173 (12)	0.0228 (12)	−0.0132 (14)
C15	0.0455 (11)	0.0835 (15)	0.0593 (12)	0.0020 (11)	0.0071 (9)	−0.0134 (11)
C16	0.0456 (10)	0.0513 (11)	0.0478 (10)	0.0069 (8)	0.0050 (8)	−0.0013 (8)
C17	0.0543 (12)	0.0731 (14)	0.0611 (12)	−0.0016 (10)	0.0079 (10)	0.0040 (10)
C18	0.0510 (13)	0.0902 (17)	0.0914 (17)	−0.0034 (12)	0.0123 (12)	0.0068 (13)
C19	0.0468 (13)	0.0979 (18)	0.1005 (19)	0.0018 (12)	−0.0048 (13)	0.0028 (15)
C20	0.0589 (14)	0.0993 (18)	0.0713 (15)	0.0133 (13)	−0.0106 (12)	0.0074 (13)
C21	0.0527 (12)	0.0615 (12)	0.0536 (11)	0.0133 (10)	0.0008 (9)	0.0018 (9)
C22	0.0708 (14)	0.0796 (15)	0.0481 (11)	0.0173 (12)	0.0045 (10)	0.0127 (10)
C23	0.0627 (13)	0.0640 (12)	0.0561 (12)	0.0143 (10)	0.0099 (10)	0.0180 (10)
C24	0.0498 (11)	0.0527 (11)	0.0400 (9)	0.0053 (9)	0.0066 (8)	−0.0004 (9)
C25	0.0488 (10)	0.0459 (10)	0.0430 (9)	−0.0001 (8)	0.0089 (8)	0.0011 (8)
C26	0.0459 (10)	0.0463 (10)	0.0405 (9)	−0.0012 (8)	0.0052 (8)	−0.0021 (8)
C27	0.0477 (11)	0.0675 (13)	0.0513 (11)	−0.0023 (9)	0.0087 (9)	−0.0026 (9)
C28	0.0552 (12)	0.0857 (15)	0.0598 (13)	−0.0180 (11)	0.0029 (10)	−0.0020 (12)
C29	0.0770 (16)	0.0750 (15)	0.0571 (13)	−0.0239 (12)	−0.0010 (11)	−0.0134 (11)
C30	0.0785 (15)	0.0562 (12)	0.0512 (11)	−0.0020 (11)	0.0167 (10)	−0.0078 (9)
N1	0.0532 (9)	0.0525 (9)	0.0414 (8)	0.0071 (7)	0.0042 (7)	−0.0086 (7)
N2	0.0461 (9)	0.0538 (9)	0.0456 (8)	0.0082 (7)	0.0108 (7)	0.0080 (7)
O1	0.0700 (9)	0.0495 (8)	0.0520 (7)	−0.0015 (6)	0.0165 (6)	−0.0113 (6)
O2	0.0526 (8)	0.0939 (11)	0.0511 (8)	−0.0098 (8)	−0.0021 (6)	0.0017 (7)
O3	0.0563 (8)	0.0822 (10)	0.0511 (8)	−0.0079 (7)	−0.0049 (6)	0.0209 (7)
O4	0.0502 (8)	0.0683 (9)	0.0553 (8)	0.0000 (6)	0.0053 (6)	−0.0208 (7)

Geometric parameters (Å, º) top

C1—C2	1.389 (2)	C16—C21	1.391 (2)
C1—C6	1.396 (3)	C16—C24	1.482 (2)
C1—C9	1.478 (3)	C17—C18	1.378 (3)
C2—C3	1.378 (3)	C17—H17	0.9300
C2—H2	0.9300	C18—C19	1.371 (3)
C3—C4	1.371 (3)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.373 (3)
C4—C5	1.380 (3)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.390 (3)
C5—C6	1.386 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.498 (3)
C6—C7	1.493 (3)	C22—C23	1.498 (3)
C7—C8	1.505 (3)	C22—H22A	0.9700
C7—H7A	0.9700	C22—H22B	0.9700
C7—H7B	0.9700	C23—N2	1.470 (2)
C8—N1	1.477 (2)	C23—H23A	0.9700
C8—H8A	0.9700	C23—H23B	0.9700
C8—H8B	0.9700	C24—O3	1.240 (2)
C9—O1	1.243 (2)	C24—N2	1.338 (2)
C9—N1	1.346 (2)	C25—C30	1.384 (3)
C10—C15	1.385 (3)	C25—C26	1.389 (2)
C10—C11	1.390 (2)	C25—N2	1.436 (2)
C10—N1	1.430 (2)	C26—O4	1.353 (2)
C11—O2	1.349 (2)	C26—C27	1.384 (2)
C11—C12	1.381 (3)	C27—C28	1.368 (3)
C12—C13	1.370 (3)	C27—H27	0.9300
C12—H12	0.9300	C28—C29	1.370 (3)
C13—C14	1.381 (3)	C28—H28	0.9300
C13—H13	0.9300	C29—C30	1.380 (3)
C14—C15	1.373 (3)	C29—H29	0.9300
C14—H14	0.9300	C30—H30	0.9300
C15—H15	0.9300	O2—H2A	0.8200
C16—C17	1.387 (3)	O4—H4A	0.8200

C2—C1—C6	119.70 (18)	C18—C17—H17	119.8
C2—C1—C9	119.77 (17)	C16—C17—H17	119.8
C6—C1—C9	120.51 (16)	C19—C18—C17	119.6 (2)
C3—C2—C1	120.46 (19)	C19—C18—H18	120.2
C3—C2—H2	119.8	C17—C18—H18	120.2
C1—C2—H2	119.8	C18—C19—C20	120.3 (2)
C4—C3—C2	119.9 (2)	C18—C19—H19	119.9
C4—C3—H3	120.0	C20—C19—H19	119.9
C2—C3—H3	120.0	C19—C20—C21	121.3 (2)
C3—C4—C5	120.2 (2)	C19—C20—H20	119.3
C3—C4—H4	119.9	C21—C20—H20	119.3
C5—C4—H4	119.9	C20—C21—C16	118.1 (2)
C4—C5—C6	120.8 (2)	C20—C21—C22	123.15 (19)
C4—C5—H5	119.6	C16—C21—C22	118.74 (17)
C6—C5—H5	119.6	C21—C22—C23	111.20 (16)
C5—C6—C1	118.84 (18)	C21—C22—H22A	109.4
C5—C6—C7	123.63 (18)	C23—C22—H22A	109.4
C1—C6—C7	117.53 (17)	C21—C22—H22B	109.4
C6—C7—C8	109.78 (16)	C23—C22—H22B	109.4
C6—C7—H7A	109.7	H22A—C22—H22B	108.0
C8—C7—H7A	109.7	N2—C23—C22	111.26 (17)
C6—C7—H7B	109.7	N2—C23—H23A	109.4
C8—C7—H7B	109.7	C22—C23—H23A	109.4
H7A—C7—H7B	108.2	N2—C23—H23B	109.4
N1—C8—C7	110.58 (15)	C22—C23—H23B	109.4
N1—C8—H8A	109.5	H23A—C23—H23B	108.0
C7—C8—H8A	109.5	O3—C24—N2	122.85 (16)
N1—C8—H8B	109.5	O3—C24—C16	119.94 (17)
C7—C8—H8B	109.5	N2—C24—C16	117.19 (15)
H8A—C8—H8B	108.1	C30—C25—C26	119.71 (17)
O1—C9—N1	121.35 (17)	C30—C25—N2	122.20 (16)
O1—C9—C1	121.52 (16)	C26—C25—N2	118.09 (15)
N1—C9—C1	117.13 (16)	O4—C26—C27	122.76 (16)
C15—C10—C11	119.36 (18)	O4—C26—C25	117.63 (15)
C15—C10—N1	121.76 (17)	C27—C26—C25	119.61 (16)
C11—C10—N1	118.88 (16)	C28—C27—C26	120.02 (19)
O2—C11—C12	123.50 (17)	C28—C27—H27	120.0
O2—C11—C10	116.48 (16)	C26—C27—H27	120.0
C12—C11—C10	120.02 (18)	C27—C28—C29	120.8 (2)
C13—C12—C11	120.0 (2)	C27—C28—H28	119.6
C13—C12—H12	120.0	C29—C28—H28	119.6
C11—C12—H12	120.0	C28—C29—C30	119.91 (19)
C12—C13—C14	120.3 (2)	C28—C29—H29	120.0
C12—C13—H13	119.9	C30—C29—H29	120.0
C14—C13—H13	119.9	C29—C30—C25	119.97 (19)
C15—C14—C13	120.0 (2)	C29—C30—H30	120.0
C15—C14—H14	120.0	C25—C30—H30	120.0
C13—C14—H14	120.0	C9—N1—C10	120.94 (15)
C14—C15—C10	120.2 (2)	C9—N1—C8	120.81 (16)
C14—C15—H15	119.9	C10—N1—C8	118.25 (14)
C10—C15—H15	119.9	C24—N2—C25	120.89 (14)
C17—C16—C21	120.20 (17)	C24—N2—C23	121.64 (15)
C17—C16—C24	119.35 (16)	C25—N2—C23	117.47 (14)
C21—C16—C24	120.32 (17)	C11—O2—H2A	109.5
C18—C17—C16	120.5 (2)	C26—O4—H4A	109.5

C6—C1—C2—C3	−1.3 (3)	C24—C16—C21—C22	5.1 (3)
C9—C1—C2—C3	−179.55 (17)	C20—C21—C22—C23	−152.4 (2)
C1—C2—C3—C4	1.0 (3)	C16—C21—C22—C23	28.7 (3)
C2—C3—C4—C5	0.5 (3)	C21—C22—C23—N2	−49.3 (2)
C3—C4—C5—C6	−1.6 (3)	C17—C16—C24—O3	−15.6 (3)
C4—C5—C6—C1	1.3 (3)	C21—C16—C24—O3	160.19 (18)
C4—C5—C6—C7	−179.17 (19)	C17—C16—C24—N2	166.28 (17)
C2—C1—C6—C5	0.2 (3)	C21—C16—C24—N2	−17.9 (3)
C9—C1—C6—C5	178.40 (16)	C30—C25—C26—O4	179.36 (16)
C2—C1—C6—C7	−179.41 (17)	N2—C25—C26—O4	0.2 (2)
C9—C1—C6—C7	−1.2 (2)	C30—C25—C26—C27	−0.4 (3)
C5—C6—C7—C8	144.45 (18)	N2—C25—C26—C27	−179.54 (16)
C1—C6—C7—C8	−36.0 (2)	O4—C26—C27—C28	179.99 (17)
C6—C7—C8—N1	54.5 (2)	C25—C26—C27—C28	−0.3 (3)
C2—C1—C9—O1	18.7 (2)	C26—C27—C28—C29	0.5 (3)
C6—C1—C9—O1	−159.50 (17)	C27—C28—C29—C30	0.0 (3)
C2—C1—C9—N1	−161.35 (16)	C28—C29—C30—C25	−0.6 (3)
C6—C1—C9—N1	20.4 (2)	C26—C25—C30—C29	0.8 (3)
C15—C10—C11—O2	178.12 (17)	N2—C25—C30—C29	179.95 (18)
N1—C10—C11—O2	−2.1 (2)	O1—C9—N1—C10	2.0 (2)
C15—C10—C11—C12	−1.0 (3)	C1—C9—N1—C10	−177.93 (15)
N1—C10—C11—C12	178.74 (16)	O1—C9—N1—C8	−178.89 (16)
O2—C11—C12—C13	−178.00 (19)	C1—C9—N1—C8	1.2 (2)
C10—C11—C12—C13	1.0 (3)	C15—C10—N1—C9	−64.9 (2)
C11—C12—C13—C14	−0.1 (3)	C11—C10—N1—C9	115.33 (18)
C12—C13—C14—C15	−0.8 (3)	C15—C10—N1—C8	115.91 (19)
C13—C14—C15—C10	0.9 (3)	C11—C10—N1—C8	−63.8 (2)
C11—C10—C15—C14	0.0 (3)	C7—C8—N1—C9	−38.9 (2)
N1—C10—C15—C14	−179.70 (18)	C7—C8—N1—C10	140.29 (16)
C21—C16—C17—C18	−1.0 (3)	O3—C24—N2—C25	−4.9 (3)
C24—C16—C17—C18	174.73 (19)	C16—C24—N2—C25	173.20 (15)
C16—C17—C18—C19	−0.5 (3)	O3—C24—N2—C23	175.84 (17)
C17—C18—C19—C20	1.2 (4)	C16—C24—N2—C23	−6.1 (2)
C18—C19—C20—C21	−0.3 (4)	C30—C25—N2—C24	82.4 (2)
C19—C20—C21—C16	−1.3 (3)	C26—C25—N2—C24	−98.5 (2)
C19—C20—C21—C22	179.8 (2)	C30—C25—N2—C23	−98.3 (2)
C17—C16—C21—C20	1.9 (3)	C26—C25—N2—C23	80.9 (2)
C24—C16—C21—C20	−173.83 (18)	C22—C23—N2—C24	40.1 (2)
C17—C16—C21—C22	−179.16 (18)	C22—C23—N2—C25	−139.19 (17)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3ⁱ	0.82	1.84	2.6388 (18)	166
O4—H4A···O1	0.82	1.85	2.6668 (17)	175
C7—H7B···Cg2ⁱⁱ	0.97	2.92	3.770 (2)	147
C19—H19···Cg2ⁱⁱⁱ	0.93	2.78	3.518 (3)	137
C23—H23A···Cg3^iv	0.97	2.87	3.771 (2)	155

Symmetry codes: (i) x, −y+2, z+1/2; (ii) −x+3/2, −y+5/2, −z+2; (iii) x+1/2, y−1/2, z; (iv) −x+3/2, −y+3/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃NO₂
M_r	239.26
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	21.350 (3), 11.0670 (14), 21.064 (3)
β (°)	100.227 (2)
V (Å³)	4897.9 (11)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.35 × 0.34

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.958, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	17755, 4559, 2998
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.120, 1.01
No. of reflections	4559
No. of parameters	326
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3ⁱ	0.82	1.84	2.6388 (18)	166
O4—H4A···O1	0.82	1.85	2.6668 (17)	175
C7—H7B···Cg2ⁱⁱ	0.9700	2.92	3.770 (2)	147
C19—H19···Cg2ⁱⁱⁱ	0.9300	2.78	3.518 (3)	137
C23—H23A···Cg3^iv	0.9700	2.87	3.771 (2)	155

Symmetry codes: (i) x, −y+2, z+1/2; (ii) −x+3/2, −y+5/2, −z+2; (iii) x+1/2, y−1/2, z; (iv) −x+3/2, −y+3/2, −z+2.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (NNSF; Nos. 30771454, 31000865).

References

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