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In the title compound, C23H15NO2, the naphthyl unit is planar and the benzo­pyran unit is nearly planar. These two moieties are inclined at an angle of 9.10 (6)° with respect to one another.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010532/qa0319sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010532/qa0319Isup2.hkl
Contains datablock I

CCDC reference: 150737

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: MolEN (Fair, 1990); data reduction: MolEN; program(s) used to solve structure: DIRDIF96 (Beurskens et al., 1996); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

6-methyl-4(2-napthyl)ethenyl-3-cyano-1-benzopyran-2-one. top
Crystal data top
C23H15NO2F(000) = 704
Mr = 337.36Dx = 1.365 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.814 (5) ÅCell parameters from 25 reflections
b = 11.561 (3) Åθ = 2–25°
c = 18.580 (7) ŵ = 0.09 mm1
β = 101.96 (4)°T = 293 K
V = 1642.0 (13) Å3Rectangular, dark yellow
Z = 40.15 × 0.12 × 0.10 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
2095 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 25°, θmin = 2.1°
ω–2θ scansh = 09
Absorption correction: ψ scan
(North et al., 1968)
k = 013
Tmin = 0.974, Tmax = 0.994l = 2221
3103 measured reflections3 standard reflections every 100 reflections
2878 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 0.83Calculated w = 1/[σ2(Fo2) + (0.0935P)2 + 0.9948P]
where P = (Fo2 + 2Fc2)/3
2878 reflections(Δ/σ)max = 0.003
238 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
O10.16468 (18)0.59649 (13)0.03667 (8)0.0497 (4)
C100.4653 (2)0.64885 (16)0.03668 (10)0.0349 (4)
C240.5272 (3)1.08238 (16)0.15173 (10)0.0416 (5)
C90.3418 (3)0.58159 (17)0.06231 (11)0.0401 (5)
C30.2280 (2)0.73490 (16)0.04991 (11)0.0392 (5)
C50.6415 (3)0.63071 (17)0.06890 (10)0.0391 (5)
H50.72630.67510.05340.064 (2)*
O100.05516 (19)0.68442 (15)0.03541 (10)0.0656 (5)
C250.6375 (3)1.16597 (17)0.17505 (11)0.0487 (5)
C40.4046 (2)0.73036 (16)0.02206 (10)0.0356 (4)
C160.3460 (3)1.08999 (19)0.18096 (12)0.0495 (5)
H160.27111.03540.16740.064 (2)*
C230.6046 (3)0.99275 (17)0.10204 (10)0.0395 (5)
C70.5643 (3)0.48205 (18)0.14475 (11)0.0480 (5)
H70.59740.42510.18030.064 (2)*
C140.5277 (2)0.80240 (16)0.05175 (10)0.0376 (4)
H140.63480.77090.05590.064 (2)*
C20.1007 (3)0.67290 (18)0.01731 (12)0.0461 (5)
C60.6931 (3)0.54873 (17)0.12306 (10)0.0418 (5)
C80.3898 (3)0.49799 (18)0.11524 (11)0.0476 (5)
H80.30560.45300.13080.064 (2)*
C150.4920 (3)0.91137 (17)0.07307 (10)0.0385 (5)
H150.38260.93900.06910.064 (2)*
C220.7826 (3)0.9874 (2)0.08072 (13)0.0511 (6)
H220.83330.92800.04970.064 (2)*
C130.8824 (3)0.5323 (2)0.15862 (13)0.0573 (6)
H1310.95430.55780.12560.122 (7)*
H1320.90430.45190.16980.122 (7)*
H1330.90950.57660.20320.122 (7)*
C180.3850 (4)1.2588 (2)0.25036 (14)0.0680 (8)
H180.33651.31730.28260.064 (2)*
C200.8189 (4)1.1572 (2)0.15012 (14)0.0619 (7)
H200.89141.21210.16490.064 (2)*
C170.2787 (4)1.1758 (2)0.22864 (13)0.0615 (7)
H170.15871.17860.24700.064 (2)*
C190.5600 (4)1.25455 (19)0.22442 (13)0.0633 (7)
H190.63101.31060.23910.064 (2)*
C120.1513 (3)0.79524 (19)0.11625 (13)0.0482 (5)
N120.0859 (3)0.8373 (2)0.17039 (13)0.0708 (6)
C210.8909 (3)1.0701 (2)0.10490 (14)0.0620 (7)
H211.01181.06490.08980.064 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0409 (8)0.0483 (9)0.0628 (9)0.0069 (7)0.0174 (7)0.0072 (7)
C100.0409 (10)0.0317 (9)0.0341 (9)0.0025 (8)0.0123 (8)0.0031 (8)
C240.0576 (13)0.0326 (10)0.0375 (10)0.0025 (9)0.0166 (9)0.0049 (8)
C90.0441 (11)0.0369 (10)0.0419 (10)0.0044 (9)0.0146 (9)0.0032 (8)
C30.0370 (10)0.0353 (10)0.0463 (11)0.0007 (8)0.0107 (8)0.0004 (8)
C50.0437 (11)0.0363 (10)0.0384 (10)0.0040 (8)0.0111 (8)0.0019 (8)
O100.0340 (9)0.0685 (11)0.0959 (13)0.0014 (8)0.0168 (8)0.0094 (10)
C250.0746 (16)0.0356 (11)0.0432 (11)0.0082 (10)0.0289 (11)0.0072 (9)
C40.0393 (10)0.0308 (9)0.0389 (10)0.0004 (8)0.0129 (8)0.0036 (8)
C160.0586 (14)0.0411 (12)0.0501 (12)0.0019 (10)0.0145 (10)0.0033 (10)
C230.0450 (11)0.0357 (10)0.0396 (10)0.0043 (8)0.0128 (8)0.0038 (8)
C70.0669 (15)0.0382 (11)0.0389 (11)0.0025 (10)0.0113 (10)0.0042 (9)
C140.0360 (10)0.0385 (10)0.0400 (10)0.0001 (8)0.0114 (8)0.0033 (8)
C20.0415 (12)0.0398 (11)0.0590 (13)0.0014 (9)0.0147 (10)0.0040 (10)
C60.0524 (12)0.0379 (10)0.0340 (10)0.0002 (9)0.0066 (9)0.0034 (8)
C80.0603 (14)0.0399 (11)0.0457 (12)0.0111 (10)0.0180 (10)0.0033 (9)
C150.0383 (10)0.0395 (11)0.0379 (10)0.0016 (8)0.0087 (8)0.0017 (8)
C220.0480 (13)0.0488 (13)0.0567 (13)0.0058 (10)0.0109 (10)0.0003 (10)
C130.0576 (14)0.0564 (14)0.0524 (13)0.0011 (11)0.0014 (11)0.0058 (11)
C180.112 (2)0.0440 (13)0.0523 (14)0.0202 (15)0.0274 (15)0.0092 (11)
C200.0777 (18)0.0478 (14)0.0699 (16)0.0211 (12)0.0378 (14)0.0087 (12)
C170.0803 (18)0.0502 (14)0.0535 (13)0.0169 (12)0.0126 (12)0.0067 (11)
C190.110 (2)0.0342 (12)0.0574 (14)0.0026 (13)0.0442 (15)0.0007 (10)
C120.0371 (11)0.0474 (12)0.0579 (13)0.0023 (9)0.0046 (10)0.0011 (10)
N120.0551 (12)0.0766 (15)0.0708 (14)0.0049 (11)0.0102 (11)0.0170 (12)
C210.0506 (14)0.0639 (16)0.0755 (17)0.0154 (12)0.0221 (12)0.0077 (13)
Geometric parameters (Å, º) top
O1—C21.352 (3)C7—C81.373 (3)
O1—C91.378 (3)C7—C61.392 (3)
C10—C91.397 (3)C7—H70.9300
C10—C51.399 (3)C14—C151.333 (3)
C10—C41.446 (3)C14—H140.9300
C24—C161.410 (3)C6—C131.502 (3)
C24—C251.421 (3)C8—H80.9300
C24—C231.435 (3)C15—H150.9300
C9—C81.374 (3)C22—C211.411 (3)
C3—C41.370 (3)C22—H220.9300
C3—C121.435 (3)C13—H1310.9600
C3—C21.456 (3)C13—H1320.9600
C5—C61.380 (3)C13—H1330.9600
C5—H50.9300C18—C191.353 (4)
O10—C21.202 (3)C18—C171.383 (4)
C25—C201.400 (4)C18—H180.9300
C25—C191.424 (3)C20—C211.357 (4)
C4—C141.464 (3)C20—H200.9300
C16—C171.361 (3)C17—H170.9300
C16—H160.9300C19—H190.9300
C23—C221.367 (3)C12—N121.139 (3)
C23—C151.464 (3)C21—H210.9300
C2—O1—C9121.90 (16)O1—C2—C3116.81 (18)
C9—C10—C5117.31 (18)C5—C6—C7118.15 (19)
C9—C10—C4118.58 (18)C5—C6—C13121.34 (19)
C5—C10—C4124.10 (17)C7—C6—C13120.51 (19)
C16—C24—C25117.66 (19)C7—C8—C9118.78 (19)
C16—C24—C23123.26 (18)C7—C8—H8120.6
C25—C24—C23119.0 (2)C9—C8—H8120.6
C8—C9—O1116.16 (18)C14—C15—C23127.73 (19)
C8—C9—C10121.99 (19)C14—C15—H15116.1
O1—C9—C10121.84 (18)C23—C15—H15116.1
C4—C3—C12123.47 (18)C23—C22—C21121.2 (2)
C4—C3—C2123.03 (18)C23—C22—H22119.4
C12—C3—C2113.41 (18)C21—C22—H22119.4
C6—C5—C10121.85 (18)C6—C13—H131109.5
C6—C5—H5119.1C6—C13—H132109.5
C10—C5—H5119.1H131—C13—H132109.5
C20—C25—C24119.1 (2)C6—C13—H133109.5
C20—C25—C19122.1 (2)H131—C13—H133109.5
C24—C25—C19118.8 (2)H132—C13—H133109.5
C3—C4—C10117.21 (17)C19—C18—C17119.6 (2)
C3—C4—C14121.66 (17)C19—C18—H18120.2
C10—C4—C14121.11 (17)C17—C18—H18120.2
C17—C16—C24121.2 (2)C21—C20—C25121.4 (2)
C17—C16—H16119.4C21—C20—H20119.3
C24—C16—H16119.4C25—C20—H20119.3
C22—C23—C24119.17 (19)C16—C17—C18121.4 (3)
C22—C23—C15121.12 (19)C16—C17—H17119.3
C24—C23—C15119.68 (18)C18—C17—H17119.3
C8—C7—C6121.87 (19)C18—C19—C25121.3 (2)
C8—C7—H7119.1C18—C19—H19119.4
C6—C7—H7119.1C25—C19—H19119.4
C15—C14—C4122.42 (18)N12—C12—C3176.0 (2)
C15—C14—H14118.8C20—C21—C22120.1 (2)
C4—C14—H14118.8C20—C21—H21120.0
O10—C2—O1118.50 (19)C22—C21—H21120.0
O10—C2—C3124.7 (2)
C2—O1—C9—C8177.5 (2)C9—O1—C2—C33.0 (3)
C2—O1—C9—C103.4 (3)C4—C3—C2—O10171.7 (2)
C5—C10—C9—C82.1 (3)C12—C3—C2—O1011.8 (3)
C4—C10—C9—C8176.5 (2)C4—C3—C2—O18.9 (3)
C5—C10—C9—O1176.9 (2)C12—C3—C2—O1167.6 (2)
C4—C10—C9—O14.5 (3)C10—C5—C6—C70.9 (3)
C9—C10—C5—C61.0 (3)C10—C5—C6—C13178.4 (2)
C4—C10—C5—C6177.6 (2)C8—C7—C6—C51.7 (3)
C16—C24—C25—C20176.6 (2)C8—C7—C6—C13177.5 (2)
C23—C24—C25—C201.3 (3)C6—C7—C8—C90.6 (3)
C16—C24—C25—C192.0 (3)O1—C9—C8—C7177.7 (2)
C23—C24—C25—C19179.9 (2)C10—C9—C8—C71.4 (3)
C12—C3—C4—C10168.4 (2)C4—C14—C15—C23178.6 (2)
C2—C3—C4—C107.8 (3)C22—C23—C15—C1430.5 (3)
C12—C3—C4—C149.9 (3)C24—C23—C15—C14151.7 (2)
C2—C3—C4—C14174.0 (2)C24—C23—C22—C211.9 (3)
C9—C10—C4—C31.1 (3)C15—C23—C22—C21175.9 (2)
C5—C10—C4—C3177.4 (2)C24—C25—C20—C210.6 (3)
C9—C10—C4—C14179.4 (2)C19—C25—C20—C21177.9 (2)
C5—C10—C4—C140.8 (3)C24—C16—C17—C180.0 (3)
C25—C24—C16—C171.3 (3)C19—C18—C17—C160.7 (4)
C23—C24—C16—C17179.2 (2)C17—C18—C19—C250.0 (4)
C16—C24—C23—C22175.3 (2)C20—C25—C19—C18177.2 (2)
C25—C24—C23—C222.6 (3)C24—C25—C19—C181.4 (3)
C16—C24—C23—C156.9 (3)C4—C3—C12—N12124.0 (3)
C25—C24—C23—C15175.3 (2)C2—C3—C12—N1252.0 (3)
C3—C4—C14—C1538.5 (3)C25—C20—C21—C221.3 (4)
C10—C4—C14—C15143.3 (2)C23—C22—C21—C200.0 (4)
C9—O1—C2—O10177.6 (2)
 

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