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The title compound, C21H29NO, forms infinite one-dimensional molecular chains via weak C—H...O interactions. The hydrogen bonding may preclude the formation of π–π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804033963/lh6343sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804033963/lh6343Isup2.hkl
Contains datablock I

CCDC reference: 263663

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.129
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: PROCESS in TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek 2003); software used to prepare material for publication: TEXSAN, SHELXL97 and PLATON.

1-(4-Decylphenyl)pyridin-4(1H)-one top
Crystal data top
C21H29NOF(000) = 680
Mr = 311.45Dx = 1.128 Mg m3
Monoclinic, P21/cMelting point: 335 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71069 Å
a = 19.4607 (10) ÅCell parameters from 25 reflections
b = 10.5889 (15) Åθ = 16.4–19.1°
c = 9.0394 (12) ŵ = 0.07 mm1
β = 99.948 (8)°T = 296 K
V = 1834.7 (4) Å3Prism, colorless
Z = 40.43 × 0.33 × 0.19 mm
Data collection top
Rigaku AFC-5S
diffractometer
Rint = 0.031
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.1°
Graphite monochromatorh = 2322
ω scansk = 120
3484 measured reflectionsl = 010
3254 independent reflections3 standard reflections every 100 reflections
1521 reflections with I > 2σ(I) intensity decay: 0.3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.0574P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
3254 reflectionsΔρmax = 0.14 e Å3
210 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0107 (15)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.59118 (8)0.07179 (16)0.29843 (19)0.0760 (5)
N10.41999 (8)0.22685 (15)0.43220 (18)0.0462 (5)
C20.48216 (11)0.2893 (2)0.4530 (2)0.0532 (6)
C30.53938 (11)0.2407 (2)0.4103 (3)0.0584 (6)
C40.53893 (11)0.1190 (2)0.3396 (2)0.0519 (6)
C50.47250 (11)0.0590 (2)0.3201 (2)0.0570 (6)
C60.41675 (11)0.1115 (2)0.3641 (2)0.0543 (6)
C70.35833 (10)0.27903 (18)0.4769 (2)0.0439 (5)
C80.32023 (10)0.2052 (2)0.5590 (2)0.0488 (5)
C90.25768 (10)0.2499 (2)0.5912 (2)0.0511 (6)
C100.23259 (10)0.36793 (19)0.5447 (2)0.0462 (5)
C110.27377 (11)0.44196 (19)0.4680 (2)0.0520 (6)
C120.33614 (11)0.39931 (19)0.4334 (2)0.0501 (6)
C130.16199 (10)0.4161 (2)0.5673 (3)0.0581 (6)
C140.12702 (10)0.3496 (2)0.6822 (2)0.0538 (6)
C150.05615 (10)0.4052 (2)0.6940 (2)0.0568 (6)
C160.02081 (10)0.3437 (2)0.8118 (2)0.0559 (6)
C170.04975 (10)0.3998 (2)0.8233 (2)0.0560 (6)
C180.08488 (10)0.3394 (2)0.9428 (2)0.0546 (6)
C190.15511 (10)0.3955 (2)0.9567 (2)0.0544 (6)
C200.19051 (10)0.3315 (2)1.0729 (2)0.0535 (6)
C210.26111 (10)0.3852 (2)1.0866 (3)0.0600 (6)
C220.29699 (12)0.3173 (2)1.1990 (3)0.0718 (7)
H20.48500.36840.49840.064*
H30.58060.28720.42700.070*
H50.46760.02010.27470.068*
H60.37460.06800.34770.065*
H80.33650.12590.59260.059*
H90.23190.19920.64550.061*
H110.25880.52310.43890.062*
H120.36270.45070.38180.060*
H13A0.16700.50450.59540.070*
H13B0.13080.41210.47140.070*
H14A0.15700.35480.77960.065*
H14B0.12130.26110.65550.065*
H15A0.06180.49450.71660.068*
H15B0.02590.39740.59710.068*
H16A0.05110.35130.90870.067*
H16B0.01490.25450.78900.067*
H17A0.04390.48930.84480.067*
H17B0.08020.39130.72680.067*
H18A0.09100.25010.92070.066*
H18B0.05410.34711.03900.066*
H19A0.14880.48420.98230.065*
H19B0.18550.39030.85980.065*
H20A0.19600.24261.04810.064*
H20B0.16030.33791.16990.064*
H21A0.25550.47331.11540.072*
H21B0.29090.38180.98890.072*
H22A0.30160.22941.17320.108*
H22B0.34240.35321.19750.108*
H22C0.26980.32621.29760.108*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0633 (10)0.0800 (13)0.0931 (13)0.0186 (9)0.0375 (9)0.0015 (10)
N10.0451 (10)0.0452 (11)0.0515 (11)0.0007 (8)0.0177 (8)0.0037 (9)
C20.0548 (14)0.0457 (13)0.0619 (15)0.0066 (11)0.0186 (11)0.0065 (11)
C30.0505 (13)0.0573 (14)0.0712 (17)0.0031 (12)0.0210 (12)0.0014 (13)
C40.0546 (13)0.0543 (14)0.0503 (14)0.0112 (12)0.0187 (11)0.0084 (11)
C50.0608 (15)0.0494 (14)0.0636 (15)0.0061 (12)0.0187 (12)0.0124 (11)
C60.0551 (13)0.0454 (13)0.0645 (15)0.0040 (11)0.0161 (11)0.0126 (12)
C70.0474 (12)0.0433 (13)0.0441 (12)0.0016 (10)0.0165 (10)0.0053 (10)
C80.0523 (13)0.0416 (12)0.0557 (13)0.0034 (10)0.0178 (10)0.0063 (10)
C90.0527 (13)0.0469 (13)0.0586 (14)0.0027 (11)0.0235 (11)0.0070 (11)
C100.0512 (13)0.0434 (13)0.0469 (13)0.0032 (10)0.0166 (10)0.0006 (10)
C110.0632 (14)0.0412 (12)0.0562 (14)0.0081 (11)0.0233 (12)0.0053 (11)
C120.0614 (14)0.0427 (12)0.0520 (14)0.0020 (11)0.0255 (11)0.0005 (10)
C130.0543 (14)0.0570 (15)0.0673 (16)0.0073 (11)0.0226 (11)0.0035 (12)
C140.0499 (13)0.0579 (14)0.0562 (14)0.0013 (11)0.0167 (11)0.0008 (11)
C150.0494 (13)0.0607 (15)0.0628 (15)0.0025 (12)0.0172 (11)0.0007 (12)
C160.0474 (13)0.0615 (15)0.0603 (15)0.0003 (11)0.0132 (10)0.0004 (12)
C170.0449 (12)0.0607 (15)0.0645 (16)0.0002 (11)0.0158 (11)0.0007 (12)
C180.0453 (13)0.0610 (15)0.0592 (15)0.0004 (11)0.0136 (11)0.0004 (12)
C190.0434 (12)0.0574 (14)0.0628 (15)0.0016 (11)0.0106 (10)0.0007 (12)
C200.0461 (13)0.0538 (14)0.0614 (14)0.0007 (10)0.0115 (11)0.0017 (11)
C210.0482 (13)0.0626 (15)0.0714 (16)0.0033 (12)0.0164 (11)0.0036 (13)
C220.0591 (15)0.0715 (17)0.092 (2)0.0040 (13)0.0324 (14)0.0105 (15)
Geometric parameters (Å, º) top
O1—C41.247 (2)C6—H60.9300
N1—C21.363 (2)C8—H80.9300
N1—C61.365 (4)C9—H90.9300
N1—C71.441 (2)C11—H110.9300
C7—C121.380 (3)C12—H120.9300
C7—C81.379 (3)C13—H13A0.9700
C2—C31.342 (3)C13—H13B0.9700
C3—C41.438 (4)C14—H14A0.9700
C4—C51.424 (3)C14—H14B0.9700
C5—C61.339 (3)C15—H15A0.9700
C8—C91.383 (3)C15—H15B0.9700
C9—C101.381 (3)C16—H16A0.9700
C10—C111.389 (3)C16—H16B0.9700
C11—C121.381 (3)C17—H17A0.9700
C10—C131.512 (3)C17—H17B0.9700
C13—C141.510 (4)C18—H18A0.9700
C14—C151.520 (3)C18—H18B0.9700
C15—C161.512 (4)C19—H19A0.9700
C16—C171.516 (3)C19—H19B0.9700
C17—C181.516 (4)C20—H20A0.9700
C18—C191.515 (3)C20—H20B0.9700
C19—C201.513 (4)C21—H21A0.9700
C20—C211.511 (3)C21—H21B0.9700
C21—C221.510 (4)C22—H22A0.9600
C2—H20.9300C22—H22B0.9600
C3—H30.9300C22—H22C0.9600
C5—H50.9300
C2—N1—C6117.87 (18)C10—C13—H13B107.9
C2—N1—C7122.5 (2)H13A—C13—H13B107.2
C6—N1—C7119.62 (18)C13—C14—H14A109.0
C3—C2—N1122.3 (2)C15—C14—H14A109.0
C2—C3—C4122.0 (2)C13—C14—H14B109.0
O1—C4—C5123.6 (2)C15—C14—H14B109.0
O1—C4—C3123.4 (2)H14A—C14—H14B107.8
C5—C4—C3113.03 (19)C16—C15—H15A108.7
C6—C5—C4122.8 (2)C14—C15—H15A108.7
C5—C6—N1121.9 (2)C16—C15—H15B108.7
C8—C7—C12120.4 (2)C14—C15—H15B108.7
C8—C7—N1119.00 (18)H15A—C15—H15B107.6
C12—C7—N1120.58 (19)C15—C16—H16A108.7
C7—C8—C9119.6 (2)C17—C16—H16A108.7
C10—C9—C8121.5 (2)C15—C16—H16B108.7
C9—C10—C11117.3 (2)C17—C16—H16B108.7
C9—C10—C13123.08 (19)H16A—C16—H16B107.6
C11—C10—C13119.5 (2)C18—C17—H17A108.7
C12—C11—C10122.3 (2)C16—C17—H17A108.7
C7—C12—C11118.8 (2)C18—C17—H17B108.7
C14—C13—C10117.6 (2)C16—C17—H17B108.7
C13—C14—C15112.9 (2)H17A—C17—H17B107.6
C16—C15—C14114.3 (2)C19—C18—H18A108.6
C15—C16—C17114.0 (2)C17—C18—H18A108.6
C18—C17—C16114.1 (2)C19—C18—H18B108.6
C19—C18—C17114.7 (2)C17—C18—H18B108.6
C20—C19—C18114.0 (2)H18A—C18—H18B107.6
C21—C20—C19114.7 (2)C20—C19—H19A108.7
C22—C21—C20114.1 (2)C18—C19—H19A108.7
C3—C2—H2118.8C20—C19—H19B108.7
N1—C2—H2118.8C18—C19—H19B108.7
C2—C3—H3119.0H19A—C19—H19B107.6
C4—C3—H3119.0C21—C20—H20A108.6
C6—C5—H5118.6C19—C20—H20A108.6
C4—C5—H5118.6C21—C20—H20B108.6
C5—C6—H6119.0C19—C20—H20B108.6
N1—C6—H6119.0H20A—C20—H20B107.6
C7—C8—H8120.2C22—C21—H21A108.7
C9—C8—H8120.2C20—C21—H21A108.7
C10—C9—H9119.2C22—C21—H21B108.7
C8—C9—H9119.2C20—C21—H21B108.7
C7—C12—H12120.6H21A—C21—H21B107.6
C11—C12—H12120.6C21—C22—H22A109.5
C12—C11—H11118.9C21—C22—H22B109.5
C10—C11—H11118.9H22A—C22—H22B109.5
C14—C13—H13A107.9C21—C22—H22C109.5
C10—C13—H13A107.9H22A—C22—H22C109.5
C14—C13—H13B107.9H22B—C22—H22C109.5
C6—N1—C2—C30.6 (3)C8—C9—C10—C111.9 (3)
C7—N1—C2—C3179.6 (2)C8—C9—C10—C13175.2 (2)
N1—C2—C3—C40.1 (3)C9—C10—C11—C122.4 (3)
C2—C3—C4—O1179.8 (2)C13—C10—C11—C12174.8 (2)
C2—C3—C4—C50.5 (3)C8—C7—C12—C112.8 (3)
O1—C4—C5—C6179.5 (2)N1—C7—C12—C11174.71 (19)
C3—C4—C5—C60.2 (3)C10—C11—C12—C70.1 (3)
C4—C5—C6—N10.4 (4)C9—C10—C13—C1417.8 (3)
C2—N1—C6—C50.9 (3)C11—C10—C13—C14165.1 (2)
C7—N1—C6—C5179.8 (2)C10—C13—C14—C15179.38 (19)
C2—N1—C7—C8131.3 (2)C13—C14—C15—C16177.98 (19)
C6—N1—C7—C849.7 (3)C14—C15—C16—C17179.83 (18)
C2—N1—C7—C1251.2 (3)C15—C16—C17—C18179.26 (18)
C6—N1—C7—C12127.8 (2)C16—C17—C18—C19179.39 (19)
C12—C7—C8—C93.3 (3)C17—C18—C19—C20178.16 (19)
N1—C7—C8—C9174.25 (19)C18—C19—C20—C21179.17 (19)
C7—C8—C9—C100.9 (3)C19—C20—C21—C22177.86 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O1i0.932.373.279 (3)166
Symmetry code: (i) x+1, y+1/2, z+1/2.
 

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