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In the title compound, C21H18N2O2, synthesized by the reaction of benzaldehyde with 2-acetyl­pyridine and KOH, the phenyl ring makes dihedral angles of 88.5 (1) and 83.9 (1)° with the two pyridine rings. The crystal packing is stabilized by weak inter­molecular C—H...O hydrogen bonds, with an H...O distance of 2.47 Å, and by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603861X/cv2125sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603861X/cv2125Isup2.hkl
Contains datablock I

CCDC reference: 624197

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.049
  • wR factor = 0.141
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

3-Phenyl-1,5-di-2-pyridylpentane-1,5-dione top
Crystal data top
C21H18N2O2Z = 2
Mr = 330.37F(000) = 348
Triclinic, P1Dx = 1.276 Mg m3
a = 8.464 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.484 (4) ÅCell parameters from 1828 reflections
c = 10.713 (4) Åθ = 2.6–27.7°
α = 94.449 (4)°µ = 0.08 mm1
β = 111.377 (4)°T = 298 K
γ = 100.396 (4)°Block, colourless
V = 860.0 (5) Å30.56 × 0.53 × 0.48 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
2983 independent reflections
Radiation source: fine-focus sealed tube2152 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 109
Tmin = 0.955, Tmax = 0.961k = 1210
4446 measured reflectionsl = 1112
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.077P)2 + 0.1387P]
where P = (Fo2 + 2Fc2)/3
2983 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

Experimental. C21 H18N2O2: Calculated: C 76.43, H 5.49, N 8.48%; Found: C 76.39, H 5.53, N 8.42%.

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
O10.2523 (2)0.04482 (13)0.32665 (13)0.0603 (4)
O20.48691 (19)0.07433 (15)0.81888 (14)0.0657 (5)
C10.3514 (2)0.14577 (17)0.33106 (17)0.0408 (4)
C20.4958 (2)0.21642 (19)0.46208 (17)0.0422 (4)
H2A0.51200.31030.46150.051*
H2B0.60330.19210.46810.051*
C30.4582 (2)0.18461 (17)0.58714 (16)0.0368 (4)
H30.42360.08890.57780.044*
C40.6205 (2)0.23188 (18)0.71847 (17)0.0412 (4)
H4A0.72030.21100.70400.049*
H4B0.64240.32650.74070.049*
C50.6017 (2)0.16999 (18)0.83613 (18)0.0423 (4)
C60.3318 (2)0.20149 (18)0.20252 (17)0.0425 (4)
N10.4275 (3)0.32040 (18)0.21427 (17)0.0646 (5)
C80.4063 (4)0.3684 (3)0.0989 (2)0.0863 (9)
H80.47140.45170.10440.104*
C90.2951 (4)0.3031 (3)0.0268 (2)0.0787 (8)
H90.28570.34150.10380.094*
C100.1989 (3)0.1815 (2)0.0373 (2)0.0697 (7)
H100.12240.13470.12150.084*
C110.2173 (3)0.1294 (2)0.07942 (19)0.0569 (6)
H110.15310.04610.07550.068*
C120.3074 (2)0.24034 (16)0.59468 (15)0.0348 (4)
C130.3174 (3)0.37470 (17)0.60856 (18)0.0445 (5)
H130.41740.43160.61200.053*
C140.1813 (3)0.4252 (2)0.6173 (2)0.0538 (5)
H140.19070.51550.62730.065*
C150.0317 (3)0.3425 (2)0.6112 (2)0.0546 (5)
H150.06040.37640.61610.066*
C160.0196 (3)0.2095 (2)0.59791 (19)0.0507 (5)
H160.08080.15310.59430.061*
C170.1562 (2)0.15925 (18)0.58995 (17)0.0411 (4)
H170.14640.06890.58120.049*
C180.7331 (2)0.22625 (18)0.97643 (18)0.0433 (5)
N20.8480 (2)0.33683 (16)0.98995 (16)0.0556 (5)
C200.9678 (3)0.3847 (2)1.1146 (2)0.0687 (7)
H201.04830.46241.12640.082*
C210.9779 (3)0.3252 (3)1.2261 (2)0.0680 (7)
H211.06480.36111.31060.082*
C220.8597 (3)0.2135 (3)1.2115 (2)0.0705 (7)
H220.86370.17211.28590.085*
C230.7334 (3)0.1620 (2)1.0848 (2)0.0602 (6)
H230.65000.08581.07220.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0732 (10)0.0495 (8)0.0462 (8)0.0116 (8)0.0221 (7)0.0026 (6)
O20.0587 (10)0.0716 (10)0.0522 (9)0.0102 (8)0.0136 (7)0.0241 (7)
C10.0435 (11)0.0396 (10)0.0388 (10)0.0028 (8)0.0191 (8)0.0020 (8)
C20.0400 (10)0.0491 (11)0.0361 (10)0.0025 (8)0.0167 (8)0.0058 (8)
C30.0371 (10)0.0371 (9)0.0341 (9)0.0024 (8)0.0136 (8)0.0074 (7)
C40.0372 (10)0.0471 (11)0.0367 (10)0.0037 (8)0.0133 (8)0.0110 (8)
C50.0391 (11)0.0468 (11)0.0413 (10)0.0073 (9)0.0154 (9)0.0141 (8)
C60.0460 (11)0.0456 (11)0.0353 (10)0.0068 (9)0.0171 (8)0.0037 (8)
N10.0775 (13)0.0567 (11)0.0438 (10)0.0142 (10)0.0190 (9)0.0088 (8)
C80.109 (2)0.0767 (17)0.0514 (14)0.0209 (15)0.0240 (14)0.0211 (12)
C90.098 (2)0.0882 (19)0.0427 (13)0.0050 (16)0.0245 (13)0.0228 (12)
C100.0821 (17)0.0781 (17)0.0328 (11)0.0056 (14)0.0106 (11)0.0034 (10)
C110.0634 (14)0.0551 (13)0.0403 (11)0.0007 (11)0.0139 (10)0.0001 (9)
C120.0369 (10)0.0389 (10)0.0235 (8)0.0033 (8)0.0079 (7)0.0054 (7)
C130.0486 (12)0.0408 (11)0.0412 (10)0.0047 (9)0.0160 (9)0.0095 (8)
C140.0666 (14)0.0445 (11)0.0505 (12)0.0187 (10)0.0195 (10)0.0091 (9)
C150.0511 (13)0.0644 (14)0.0520 (12)0.0211 (11)0.0204 (10)0.0082 (10)
C160.0407 (11)0.0626 (13)0.0454 (11)0.0040 (10)0.0169 (9)0.0045 (9)
C170.0398 (10)0.0407 (10)0.0372 (10)0.0012 (8)0.0131 (8)0.0026 (8)
C180.0448 (11)0.0492 (11)0.0376 (10)0.0121 (9)0.0162 (9)0.0106 (8)
N20.0586 (11)0.0540 (10)0.0422 (10)0.0017 (9)0.0111 (8)0.0061 (8)
C200.0701 (16)0.0646 (14)0.0484 (13)0.0005 (12)0.0064 (11)0.0025 (11)
C210.0760 (17)0.0774 (16)0.0368 (12)0.0224 (14)0.0061 (11)0.0028 (11)
C220.0924 (19)0.0823 (17)0.0372 (12)0.0271 (15)0.0202 (12)0.0183 (11)
C230.0680 (15)0.0666 (14)0.0440 (12)0.0087 (11)0.0204 (11)0.0178 (10)
Geometric parameters (Å, º) top
O1—C11.212 (2)C11—H110.9300
O2—C51.213 (2)C12—C171.384 (2)
C1—C61.503 (2)C12—C131.389 (2)
C1—C21.508 (3)C13—C141.381 (3)
C2—C31.533 (2)C13—H130.9300
C2—H2A0.9700C14—C151.376 (3)
C2—H2B0.9700C14—H140.9300
C3—C121.521 (2)C15—C161.372 (3)
C3—C41.533 (2)C15—H150.9300
C3—H30.9800C16—C171.381 (3)
C4—C51.507 (2)C16—H160.9300
C4—H4A0.9700C17—H170.9300
C4—H4B0.9700C18—N21.332 (2)
C5—C181.501 (3)C18—C231.386 (3)
C6—N11.328 (2)N2—C201.337 (3)
C6—C111.378 (3)C20—C211.373 (3)
N1—C81.334 (3)C20—H200.9300
C8—C91.367 (3)C21—C221.353 (3)
C8—H80.9300C21—H210.9300
C9—C101.355 (3)C22—C231.377 (3)
C9—H90.9300C22—H220.9300
C10—C111.372 (3)C23—H230.9300
C10—H100.9300
O1—C1—C6119.34 (16)C10—C11—C6119.3 (2)
O1—C1—C2121.75 (16)C10—C11—H11120.3
C6—C1—C2118.91 (15)C6—C11—H11120.3
C1—C2—C3112.54 (15)C17—C12—C13117.56 (17)
C1—C2—H2A109.1C17—C12—C3121.27 (15)
C3—C2—H2A109.1C13—C12—C3121.16 (16)
C1—C2—H2B109.1C14—C13—C12121.07 (18)
C3—C2—H2B109.1C14—C13—H13119.5
H2A—C2—H2B107.8C12—C13—H13119.5
C12—C3—C2111.39 (14)C15—C14—C13120.28 (19)
C12—C3—C4110.97 (14)C15—C14—H14119.9
C2—C3—C4111.74 (14)C13—C14—H14119.9
C12—C3—H3107.5C16—C15—C14119.48 (19)
C2—C3—H3107.5C16—C15—H15120.3
C4—C3—H3107.5C14—C15—H15120.3
C5—C4—C3112.39 (15)C15—C16—C17120.15 (19)
C5—C4—H4A109.1C15—C16—H16119.9
C3—C4—H4A109.1C17—C16—H16119.9
C5—C4—H4B109.1C16—C17—C12121.46 (17)
C3—C4—H4B109.1C16—C17—H17119.3
H4A—C4—H4B107.9C12—C17—H17119.3
O2—C5—C18120.10 (15)N2—C18—C23122.84 (18)
O2—C5—C4121.47 (16)N2—C18—C5117.21 (15)
C18—C5—C4118.39 (16)C23—C18—C5119.95 (18)
N1—C6—C11123.00 (17)C18—N2—C20116.99 (17)
N1—C6—C1117.27 (16)N2—C20—C21123.4 (2)
C11—C6—C1119.73 (17)N2—C20—H20118.3
C6—N1—C8116.14 (18)C21—C20—H20118.3
N1—C8—C9124.3 (2)C22—C21—C20119.2 (2)
N1—C8—H8117.8C22—C21—H21120.4
C9—C8—H8117.8C20—C21—H21120.4
C10—C9—C8118.9 (2)C21—C22—C23119.0 (2)
C10—C9—H9120.5C21—C22—H22120.5
C8—C9—H9120.5C23—C22—H22120.5
C9—C10—C11118.3 (2)C22—C23—C18118.6 (2)
C9—C10—H10120.9C22—C23—H23120.7
C11—C10—H10120.9C18—C23—H23120.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···O2i0.932.473.289 (3)147
Symmetry code: (i) x+1, y, z+2.
 

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