organic compounds
3-(6-Methoxy-2-naphthyl)-1-(2-pyridyl)prop-2-en-1-one
aYibin Vocational & Technical College, Si chuan, People's Republic of China
*Correspondence e-mail: yaocheng@njut.edu.cn
There are two molecules in the 19H15NO2, 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.
of the title compound, CExperimental
Crystal data
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Data collection
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell 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
10.1107/S1600536810016880/hb5431sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810016880/hb5431Isup2.hkl
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).
The
of the title compound is indeterminate in the present H atoms were positioned geometrically, with C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
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).C19H15NO2 | Dx = 1.310 Mg m−3 |
Mr = 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 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.067 |
Radiation source: fine-focus sealed tube | θmax = 25.3°, θmin = 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 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(Fo2) + (0.0012P)2] where P = (Fo2 + 2Fc2)/3 |
5329 reflections | (Δ/σ)max < 0.001 |
397 parameters | Δρmax = 0.16 e Å−3 |
4 restraints | Δρmin = −0.18 e Å−3 |
C19H15NO2 | V = 2933.6 (10) Å3 |
Mr = 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 |
Enraf–Nonius CAD-4 diffractometer | Rint = 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) |
R[F2 > 2σ(F2)] = 0.071 | 4 restraints |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.16 e Å−3 |
5329 reflections | Δρmin = −0.18 e Å−3 |
397 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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 |
Mr | 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 |
Rint | 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 |
Δρmax, Δρmin (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).
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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