3-(6-Meth­oxy-2-naphth­yl)-1-(2-pyrid­yl)prop-2-en-1-one

Li, X.

doi:10.1107/S1600536810016880

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1613

doi:10.1107/S1600536810016880

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3-(6-Methoxy-2-naphthyl)-1-(2-pyridyl)prop-2-en-1-one

Xiang-biao Li ^a ^*

^aYibin Vocational & Technical College, Si chuan, People's Republic of China
^*Correspondence e-mail: yaocheng@njut.edu.cn

(Received 29 April 2010; accepted 8 May 2010; online 9 June 2010)

There are two molecules in the asymmetric unit of the title compound, C₁₉H₁₅NO₂, in which the dihedral angles between the naphthalene ring system and the pyridine ring are 40.5 (3) and 41.2 (4)°. In the crystal, C—H⋯O hydrogen bonds link the molecules.

Related literature

For medicinal background, see: Petrov et al. (2006 ).

Experimental

Crystal data

C₁₉H₁₅NO₂
M_r = 289.32
Orthorhombic, P c a 2₁
a = 7.8560 (16) Å
b = 11.542 (2) Å
c = 32.353 (7) Å
V = 2933.6 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
5329 measured reflections
5329 independent reflections
2245 reflections with I > 2σ(I)
R_int = 0.067
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.071
wR(F²) = 0.080
S = 1.01
5329 reflections
397 parameters
4 restraints
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
C38—H38B⋯O1ⁱ	0.96	2.53	3.356 (10)	143
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+1, z]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); 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: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016880/hb5431sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810016880/hb5431Isup2.hkl

checkCIF report

Related literature top

For medicinal background, see: Petrov et al. (2006).

Experimental top

In the presence of sodium hydroxide, 6-methoxy-2-naphthaldehyde and 1-(pyridin-2-yl)ethanone in liquid ammonia were stirred at 313 K for 4 h. Sodium hydroxide was filtered off and the filtrate was duluted with dichlormethane and washed by brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to give crude product which was recrystallised from from dichlormethane to give yellow blocks of (I).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Ellipsoid plot.

3-(6-Methoxy-2-naphthyl)-1-(2-pyridyl)prop-2-en-1-one top

Crystal data top

C₁₉H₁₅NO₂	D_x = 1.310 Mg m⁻³
M_r = 289.32	Melting point: 513 K
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 25 reflections
a = 7.8560 (16) Å	θ = 9–12°
b = 11.542 (2) Å	µ = 0.09 mm⁻¹
c = 32.353 (7) Å	T = 293 K
V = 2933.6 (10) Å³	Needle, yellow
Z = 8	0.20 × 0.10 × 0.10 mm
F(000) = 1216

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.067
Radiation source: fine-focus sealed tube	θ_max = 25.3°, θ_min = 1.3°
Graphite monochromator	h = 0→9
ω/2θ scans	k = 0→13
5329 Please give correct value measured reflections	l = −38→38
5329 independent reflections	3 standard reflections every 200 reflections
2245 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0012P)²] where P = (F_o² + 2F_c²)/3
5329 reflections	(Δ/σ)_max < 0.001
397 parameters	Δρ_max = 0.16 e Å⁻³
4 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₉H₁₅NO₂	V = 2933.6 (10) Å³
M_r = 289.32	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 7.8560 (16) Å	µ = 0.09 mm⁻¹
b = 11.542 (2) Å	T = 293 K
c = 32.353 (7) Å	0.20 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.067
5329 Please give correct value measured reflections	3 standard reflections every 200 reflections
5329 independent reflections	intensity decay: 1%
2245 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.071	4 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.01	Δρ_max = 0.16 e Å⁻³
5329 reflections	Δρ_min = −0.18 e Å⁻³
397 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.7960 (7)	0.2745 (4)	0.4482 (2)	0.0861 (18)
O2	0.3909 (6)	0.1159 (4)	0.14036 (15)	0.0620 (14)
N1	0.8162 (10)	−0.0296 (6)	0.46063 (19)	0.058 (2)
C1	0.8679 (12)	−0.1063 (8)	0.4882 (3)	0.075 (3)
H1B	0.8507	−0.1840	0.4819	0.090*
C2	0.9437 (11)	−0.0822 (9)	0.5249 (3)	0.073 (3)
H2A	0.9850	−0.1410	0.5418	0.088*
C3	0.9574 (13)	0.0347 (9)	0.5365 (3)	0.081 (3)
H3A	0.9990	0.0564	0.5623	0.097*
C4	0.9069 (13)	0.1144 (8)	0.5081 (2)	0.062 (3)
H4A	0.9192	0.1928	0.5141	0.075*
C5	0.8360 (11)	0.0813 (7)	0.4697 (3)	0.059 (2)
C6	0.7680 (9)	0.1729 (6)	0.4408 (2)	0.058 (2)
C7	0.6862 (8)	0.1310 (6)	0.40378 (19)	0.0527 (18)
H7A	0.6472	0.0550	0.4027	0.063*
C8	0.6656 (9)	0.2015 (6)	0.37045 (19)	0.0478 (19)
H8A	0.7015	0.2778	0.3735	0.057*
C9	0.5936 (10)	0.1705 (6)	0.3306 (2)	0.0489 (19)
C10	0.6365 (9)	0.2318 (6)	0.29665 (17)	0.0415 (18)
H10A	0.7065	0.2964	0.2992	0.050*
C11	0.5771 (8)	0.1993 (5)	0.2577 (2)	0.0454 (17)
C12	0.6205 (8)	0.2602 (6)	0.22134 (19)	0.049 (2)
H12A	0.6951	0.3225	0.2232	0.059*
C13	0.5558 (9)	0.2302 (6)	0.18330 (18)	0.054 (2)
H13A	0.5861	0.2725	0.1600	0.065*
C14	0.4439 (9)	0.1356 (6)	0.1796 (2)	0.054 (2)
C15	0.3968 (8)	0.0729 (6)	0.2144 (2)	0.053 (2)
H15A	0.3228	0.0103	0.2120	0.063*
C16	0.4615 (8)	0.1045 (6)	0.2532 (2)	0.0433 (17)
C17	0.4135 (9)	0.0422 (6)	0.2887 (2)	0.0473 (19)
H17A	0.3393	−0.0203	0.2864	0.057*
C18	0.4779 (8)	0.0745 (6)	0.3275 (2)	0.052 (2)
H18A	0.4458	0.0339	0.3511	0.063*
C19	0.2639 (13)	0.0281 (7)	0.1341 (3)	0.073 (3)
H19A	0.2370	0.0230	0.1052	0.110*
H19B	0.1631	0.0478	0.1494	0.110*
H19C	0.3067	−0.0452	0.1435	0.110*
O3	−0.0515 (7)	0.2385 (5)	0.11856 (18)	0.0871 (18)
O4	0.3447 (6)	0.3763 (4)	0.42812 (15)	0.0726 (15)
N2	−0.0607 (10)	0.5392 (7)	0.1072 (2)	0.072 (2)
C20	−0.1230 (14)	0.6188 (8)	0.0806 (3)	0.079 (3)
H20A	−0.1219	0.6963	0.0884	0.094*
C21	−0.1890 (14)	0.5899 (9)	0.0420 (3)	0.090 (4)
H21A	−0.2152	0.6475	0.0230	0.107*
C22	−0.2144 (14)	0.4768 (9)	0.0325 (3)	0.080 (3)
H22A	−0.2674	0.4554	0.0080	0.096*
C23	−0.1595 (11)	0.3954 (9)	0.0602 (3)	0.071 (3)
H23A	−0.1754	0.3169	0.0549	0.085*
C24	−0.0819 (10)	0.4303 (7)	0.0953 (2)	0.0412 (19)
C25	−0.0261 (9)	0.3403 (7)	0.1266 (2)	0.059 (2)
C26	0.0593 (9)	0.3751 (6)	0.16455 (19)	0.060 (2)
H26A	0.1091	0.4481	0.1660	0.073*
C27	0.0680 (9)	0.3057 (6)	0.1972 (2)	0.052 (2)
H27A	0.0192	0.2326	0.1947	0.062*
C28	0.1465 (8)	0.3335 (6)	0.2362 (2)	0.0470 (19)
C29	0.1024 (8)	0.2713 (6)	0.2717 (2)	0.0483 (19)
H29A	0.0288	0.2086	0.2691	0.058*
C30	0.1640 (8)	0.2993 (5)	0.3108 (2)	0.0452 (18)
C31	0.1138 (10)	0.2353 (7)	0.3453 (2)	0.071 (3)
H31A	0.0394	0.1732	0.3423	0.085*
C32	0.1747 (9)	0.2641 (6)	0.3839 (2)	0.061 (2)
H32A	0.1413	0.2220	0.4071	0.074*
C33	0.2896 (8)	0.3591 (6)	0.3880 (2)	0.0485 (19)
C34	0.3415 (8)	0.4223 (6)	0.3555 (2)	0.0496 (19)
H34A	0.4181	0.4829	0.3589	0.059*
C35	0.2762 (8)	0.3942 (6)	0.3156 (2)	0.0474 (18)
C36	0.3226 (10)	0.4554 (6)	0.2796 (2)	0.054 (2)
H36A	0.3981	0.5171	0.2820	0.065*
C37	0.2623 (8)	0.4281 (6)	0.2421 (2)	0.055 (2)
H37A	0.2964	0.4715	0.2193	0.066*
C38	0.4780 (14)	0.4655 (7)	0.4339 (3)	0.094 (3)
H38A	0.5073	0.4705	0.4626	0.141*
H38B	0.4360	0.5391	0.4245	0.141*
H38C	0.5771	0.4447	0.4182	0.141*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.114 (5)	0.051 (3)	0.093 (4)	−0.004 (3)	−0.023 (4)	−0.014 (3)
O2	0.068 (4)	0.059 (3)	0.059 (4)	−0.006 (3)	0.001 (3)	−0.004 (3)
N1	0.076 (5)	0.064 (4)	0.036 (4)	−0.009 (5)	−0.003 (4)	0.025 (3)
C1	0.067 (6)	0.076 (6)	0.082 (7)	0.019 (5)	0.005 (6)	0.047 (5)
C2	0.045 (5)	0.108 (8)	0.067 (6)	0.001 (6)	−0.021 (5)	0.042 (6)
C3	0.059 (7)	0.122 (8)	0.062 (7)	−0.018 (7)	0.014 (5)	0.004 (7)
C4	0.078 (7)	0.066 (6)	0.044 (5)	−0.012 (5)	0.032 (5)	0.008 (5)
C5	0.058 (6)	0.055 (5)	0.064 (6)	−0.006 (5)	−0.003 (5)	0.002 (4)
C6	0.052 (5)	0.050 (5)	0.073 (6)	−0.001 (4)	0.004 (4)	0.000 (4)
C7	0.044 (5)	0.064 (5)	0.050 (4)	−0.003 (4)	−0.008 (4)	0.001 (4)
C8	0.054 (5)	0.040 (4)	0.050 (5)	0.013 (4)	0.006 (4)	−0.011 (4)
C9	0.064 (5)	0.040 (4)	0.043 (4)	0.006 (4)	0.003 (4)	−0.005 (3)
C10	0.047 (4)	0.040 (4)	0.038 (4)	−0.004 (3)	0.011 (4)	−0.004 (3)
C11	0.036 (4)	0.036 (4)	0.064 (5)	0.001 (3)	0.015 (4)	−0.012 (4)
C12	0.038 (4)	0.057 (5)	0.052 (5)	−0.013 (4)	−0.003 (4)	−0.001 (4)
C13	0.072 (5)	0.065 (5)	0.025 (4)	−0.008 (5)	−0.007 (4)	0.014 (4)
C14	0.058 (5)	0.045 (5)	0.058 (5)	0.008 (4)	0.005 (4)	−0.010 (4)
C15	0.054 (5)	0.041 (5)	0.064 (5)	−0.001 (4)	0.003 (4)	0.003 (4)
C16	0.044 (4)	0.042 (4)	0.044 (4)	0.006 (3)	0.004 (4)	0.012 (4)
C17	0.039 (4)	0.044 (4)	0.059 (5)	−0.009 (4)	0.011 (4)	0.003 (4)
C18	0.047 (5)	0.050 (5)	0.059 (5)	0.009 (4)	0.012 (4)	0.006 (4)
C19	0.055 (6)	0.095 (7)	0.070 (6)	−0.028 (5)	0.002 (5)	0.004 (5)
O3	0.128 (5)	0.052 (4)	0.081 (4)	−0.005 (4)	−0.005 (4)	−0.007 (3)
O4	0.075 (4)	0.083 (4)	0.059 (4)	−0.003 (3)	−0.006 (3)	−0.007 (3)
N2	0.056 (5)	0.066 (5)	0.094 (6)	0.018 (5)	0.003 (4)	−0.015 (5)
C20	0.095 (8)	0.069 (6)	0.072 (7)	0.006 (6)	0.025 (6)	−0.019 (6)
C21	0.106 (9)	0.094 (8)	0.069 (7)	0.037 (7)	0.021 (7)	0.009 (6)
C22	0.060 (7)	0.114 (8)	0.066 (7)	0.020 (7)	−0.037 (5)	0.003 (7)
C23	0.052 (6)	0.097 (7)	0.062 (6)	0.003 (5)	−0.012 (5)	−0.032 (6)
C24	0.040 (5)	0.053 (5)	0.031 (4)	0.010 (4)	0.015 (4)	0.007 (4)
C25	0.070 (6)	0.048 (5)	0.058 (5)	0.007 (4)	0.018 (4)	−0.007 (4)
C26	0.075 (6)	0.062 (5)	0.044 (4)	−0.010 (5)	−0.005 (4)	−0.001 (4)
C27	0.038 (5)	0.058 (5)	0.060 (5)	0.008 (4)	0.006 (4)	0.007 (4)
C28	0.022 (4)	0.057 (5)	0.061 (5)	0.007 (4)	−0.002 (4)	0.020 (4)
C29	0.042 (4)	0.034 (4)	0.069 (5)	−0.001 (3)	−0.010 (4)	0.004 (4)
C30	0.052 (5)	0.024 (4)	0.059 (5)	0.004 (3)	0.001 (4)	0.017 (3)
C31	0.074 (6)	0.059 (6)	0.080 (6)	−0.005 (5)	0.009 (5)	0.002 (5)
C32	0.049 (5)	0.036 (4)	0.098 (6)	−0.007 (4)	0.034 (5)	0.004 (4)
C33	0.050 (5)	0.055 (5)	0.040 (4)	0.006 (4)	−0.007 (4)	−0.004 (4)
C34	0.048 (5)	0.041 (4)	0.059 (5)	−0.002 (4)	−0.008 (4)	0.005 (4)
C35	0.037 (4)	0.051 (5)	0.055 (4)	0.003 (4)	0.005 (4)	0.002 (4)
C36	0.064 (5)	0.037 (4)	0.060 (5)	−0.003 (4)	−0.002 (4)	0.004 (4)
C37	0.044 (5)	0.056 (5)	0.066 (5)	0.009 (4)	0.014 (4)	0.017 (4)
C38	0.097 (8)	0.101 (7)	0.083 (7)	0.011 (7)	−0.016 (6)	−0.032 (6)

Geometric parameters (Å, º) top

O1—C6	1.217 (7)	O3—C25	1.219 (8)
O2—C14	1.355 (8)	O4—C33	1.383 (7)
O2—C19	1.436 (8)	O4—C38	1.480 (9)
N1—C1	1.320 (9)	N2—C24	1.325 (10)
N1—C5	1.323 (10)	N2—C20	1.351 (11)
C1—C2	1.357 (12)	C20—C21	1.393 (13)
C1—H1B	0.9300	C20—H20A	0.9300
C2—C3	1.404 (12)	C21—C22	1.355 (12)
C2—H2A	0.9300	C21—H21A	0.9300
C3—C4	1.359 (12)	C22—C23	1.368 (12)
C3—H3A	0.9300	C22—H22A	0.9300
C4—C5	1.415 (11)	C23—C24	1.352 (10)
C4—H4A	0.9300	C23—H23A	0.9300
C5—C6	1.509 (10)	C24—C25	1.516 (10)
C6—C7	1.443 (8)	C25—C26	1.455 (9)
C7—C8	1.361 (8)	C26—C27	1.328 (8)
C7—H7A	0.9300	C26—H26A	0.9300
C8—C9	1.453 (8)	C27—C28	1.442 (9)
C8—H8A	0.9300	C27—H27A	0.9300
C9—C10	1.349 (8)	C28—C29	1.398 (9)
C9—C18	1.437 (8)	C28—C37	1.433 (9)
C10—C11	1.396 (8)	C29—C30	1.391 (8)
C10—H10A	0.9300	C29—H29A	0.9300
C11—C12	1.411 (9)	C30—C31	1.397 (9)
C11—C16	1.430 (7)	C30—C35	1.414 (8)
C12—C13	1.376 (7)	C31—C32	1.379 (10)
C12—H12A	0.9300	C31—H31A	0.9300
C13—C14	1.407 (8)	C32—C33	1.426 (8)
C13—H13A	0.9300	C32—H32A	0.9300
C14—C15	1.390 (9)	C33—C34	1.342 (9)
C15—C16	1.403 (8)	C34—C35	1.427 (8)
C15—H15A	0.9300	C34—H34A	0.9300
C16—C17	1.405 (8)	C35—C36	1.410 (9)
C17—C18	1.404 (9)	C36—C37	1.340 (9)
C17—H17A	0.9300	C36—H36A	0.9300
C18—H18A	0.9300	C37—H37A	0.9300
C19—H19A	0.9600	C38—H38A	0.9600
C19—H19B	0.9600	C38—H38B	0.9600
C19—H19C	0.9600	C38—H38C	0.9600

C14—O2—C19	117.7 (7)	C33—O4—C38	116.0 (7)
C1—N1—C5	117.6 (8)	C24—N2—C20	114.5 (8)
N1—C1—C2	126.0 (9)	N2—C20—C21	122.9 (9)
N1—C1—H1B	117.0	N2—C20—H20A	118.5
C2—C1—H1B	117.0	C21—C20—H20A	118.5
C1—C2—C3	117.7 (9)	C22—C21—C20	119.3 (10)
C1—C2—H2A	121.2	C22—C21—H21A	120.4
C3—C2—H2A	121.2	C20—C21—H21A	120.4
C4—C3—C2	116.6 (9)	C21—C22—C23	117.9 (9)
C4—C3—H3A	121.7	C21—C22—H22A	121.1
C2—C3—H3A	121.7	C23—C22—H22A	121.1
C3—C4—C5	121.7 (9)	C24—C23—C22	119.1 (9)
C3—C4—H4A	119.2	C24—C23—H23A	120.4
C5—C4—H4A	119.2	C22—C23—H23A	120.4
N1—C5—C4	120.1 (8)	N2—C24—C23	125.8 (8)
N1—C5—C6	120.0 (8)	N2—C24—C25	114.8 (7)
C4—C5—C6	119.6 (8)	C23—C24—C25	119.2 (8)
O1—C6—C7	124.6 (7)	O3—C25—C26	121.5 (7)
O1—C6—C5	119.3 (7)	O3—C25—C24	118.0 (8)
C7—C6—C5	115.9 (7)	C26—C25—C24	120.5 (7)
C8—C7—C6	120.7 (7)	C27—C26—C25	121.9 (7)
C8—C7—H7A	119.7	C27—C26—H26A	119.1
C6—C7—H7A	119.7	C25—C26—H26A	119.1
C7—C8—C9	127.0 (7)	C26—C27—C28	125.8 (7)
C7—C8—H8A	116.5	C26—C27—H27A	117.1
C9—C8—H8A	116.5	C28—C27—H27A	117.1
C10—C9—C18	120.4 (7)	C29—C28—C37	116.1 (7)
C10—C9—C8	119.7 (7)	C29—C28—C27	119.9 (7)
C18—C9—C8	119.9 (6)	C37—C28—C27	123.8 (6)
C9—C10—C11	120.7 (7)	C30—C29—C28	122.7 (7)
C9—C10—H10A	119.6	C30—C29—H29A	118.7
C11—C10—H10A	119.6	C28—C29—H29A	118.7
C10—C11—C12	122.6 (6)	C29—C30—C31	120.4 (7)
C10—C11—C16	120.6 (6)	C29—C30—C35	119.8 (6)
C12—C11—C16	116.8 (7)	C31—C30—C35	119.8 (7)
C13—C12—C11	122.1 (7)	C32—C31—C30	120.0 (8)
C13—C12—H12A	119.0	C32—C31—H31A	120.0
C11—C12—H12A	119.0	C30—C31—H31A	120.0
C12—C13—C14	120.2 (7)	C31—C32—C33	119.2 (7)
C12—C13—H13A	119.9	C31—C32—H32A	120.4
C14—C13—H13A	119.9	C33—C32—H32A	120.4
O2—C14—C15	126.2 (7)	C34—C33—O4	124.2 (7)
O2—C14—C13	113.8 (7)	C34—C33—C32	122.6 (7)
C15—C14—C13	120.1 (7)	O4—C33—C32	113.2 (7)
C14—C15—C16	119.6 (7)	C33—C34—C35	118.4 (7)
C14—C15—H15A	120.2	C33—C34—H34A	120.8
C16—C15—H15A	120.2	C35—C34—H34A	120.8
C15—C16—C17	120.0 (7)	C36—C35—C30	117.3 (7)
C15—C16—C11	121.3 (6)	C36—C35—C34	122.8 (6)
C17—C16—C11	118.7 (7)	C30—C35—C34	120.0 (7)
C18—C17—C16	119.8 (7)	C37—C36—C35	122.6 (8)
C18—C17—H17A	120.1	C37—C36—H36A	118.7
C16—C17—H17A	120.1	C35—C36—H36A	118.7
C17—C18—C9	119.7 (6)	C36—C37—C28	121.5 (7)
C17—C18—H18A	120.2	C36—C37—H37A	119.2
C9—C18—H18A	120.2	C28—C37—H37A	119.2
O2—C19—H19A	109.5	O4—C38—H38A	109.5
O2—C19—H19B	109.5	O4—C38—H38B	109.5
H19A—C19—H19B	109.5	H38A—C38—H38B	109.5
O2—C19—H19C	109.5	O4—C38—H38C	109.5
H19A—C19—H19C	109.5	H38A—C38—H38C	109.5
H19B—C19—H19C	109.5	H38B—C38—H38C	109.5

C5—N1—C1—C2	−1.6 (16)	C24—N2—C20—C21	−6.1 (15)
N1—C1—C2—C3	5.3 (16)	N2—C20—C21—C22	9.5 (18)
C1—C2—C3—C4	−5.7 (14)	C20—C21—C22—C23	−5.7 (18)
C2—C3—C4—C5	3.1 (15)	C21—C22—C23—C24	−0.5 (17)
C1—N1—C5—C4	−1.4 (14)	C20—N2—C24—C23	−0.7 (12)
C1—N1—C5—C6	−175.6 (8)	C20—N2—C24—C25	−175.0 (8)
C3—C4—C5—N1	0.5 (15)	C22—C23—C24—N2	4.0 (14)
C3—C4—C5—C6	174.7 (9)	C22—C23—C24—C25	178.1 (8)
N1—C5—C6—O1	−175.6 (8)	N2—C24—C25—O3	175.7 (7)
C4—C5—C6—O1	10.2 (12)	C23—C24—C25—O3	1.0 (11)
N1—C5—C6—C7	−1.1 (11)	N2—C24—C25—C26	−5.9 (10)
C4—C5—C6—C7	−175.4 (7)	C23—C24—C25—C26	179.4 (7)
O1—C6—C7—C8	13.6 (11)	O3—C25—C26—C27	−20.5 (12)
C5—C6—C7—C8	−160.5 (7)	C24—C25—C26—C27	161.1 (7)
C6—C7—C8—C9	176.9 (7)	C25—C26—C27—C28	−178.6 (6)
C7—C8—C9—C10	−155.4 (7)	C26—C27—C28—C29	159.6 (7)
C7—C8—C9—C18	24.3 (11)	C26—C27—C28—C37	−16.2 (12)
C18—C9—C10—C11	−3.6 (11)	C37—C28—C29—C30	0.9 (10)
C8—C9—C10—C11	176.1 (6)	C27—C28—C29—C30	−175.2 (6)
C9—C10—C11—C12	−179.3 (7)	C28—C29—C30—C31	179.0 (7)
C9—C10—C11—C16	3.7 (10)	C28—C29—C30—C35	0.0 (10)
C10—C11—C12—C13	−177.4 (6)	C29—C30—C31—C32	−179.6 (7)
C16—C11—C12—C13	−0.2 (10)	C35—C30—C31—C32	−0.5 (11)
C11—C12—C13—C14	−0.6 (11)	C30—C31—C32—C33	−0.3 (12)
C19—O2—C14—C15	5.2 (10)	C38—O4—C33—C34	−4.3 (10)
C19—O2—C14—C13	−174.2 (6)	C38—O4—C33—C32	173.8 (6)
C12—C13—C14—O2	−179.8 (6)	C31—C32—C33—C34	0.0 (11)
C12—C13—C14—C15	0.8 (11)	C31—C32—C33—O4	−178.1 (7)
O2—C14—C15—C16	−179.4 (6)	O4—C33—C34—C35	179.1 (6)
C13—C14—C15—C16	−0.1 (10)	C32—C33—C34—C35	1.2 (10)
C14—C15—C16—C17	179.5 (7)	C29—C30—C35—C36	−1.1 (9)
C14—C15—C16—C11	−0.8 (10)	C31—C30—C35—C36	179.9 (7)
C10—C11—C16—C15	178.1 (6)	C29—C30—C35—C34	−179.2 (6)
C12—C11—C16—C15	0.9 (9)	C31—C30—C35—C34	1.7 (10)
C10—C11—C16—C17	−2.2 (9)	C33—C34—C35—C36	179.9 (7)
C12—C11—C16—C17	−179.4 (6)	C33—C34—C35—C30	−2.1 (10)
C15—C16—C17—C18	−179.7 (6)	C30—C35—C36—C37	1.3 (11)
C11—C16—C17—C18	0.6 (10)	C34—C35—C36—C37	179.4 (7)
C16—C17—C18—C9	−0.5 (10)	C35—C36—C37—C28	−0.4 (11)
C10—C9—C18—C17	2.0 (11)	C29—C28—C37—C36	−0.7 (10)
C8—C9—C18—C17	−177.7 (6)	C27—C28—C37—C36	175.3 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C38—H38B···O1ⁱ	0.96	2.53	3.356 (10)	143

Symmetry code: (i) x−1/2, −y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅NO₂
M_r	289.32
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	7.8560 (16), 11.542 (2), 32.353 (7)
V (Å³)	2933.6 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5329 Please give correct value, 5329, 2245
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.080, 1.01
No. of reflections	5329
No. of parameters	397
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C38—H38B···O1ⁱ	0.96	2.53	3.356 (10)	143

Symmetry code: (i) x−1/2, −y+1, z.

References

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft. The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Petrov, K. G., Zhang, Y.-M., Carter, M., Cockerill, G. S., Dickerson, S., Gauthier, C. A., Guo, Y., Mook, R. A., Rusnak, D. W., Walker, A. L., Wood, E. R. & Lackey, K. E. (2006). Bioorg. Med. Chem. Lett. 16, 4686–4691. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 7| July 2010| Page o1613

doi:10.1107/S1600536810016880

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