The title compound, C
21H
29NO, 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
CCDC reference: 263663
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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(1
H)-one
top
Crystal data top
C21H29NO | F(000) = 680 |
Mr = 311.45 | Dx = 1.128 Mg m−3 |
Monoclinic, P21/c | Melting point: 335 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71069 Å |
a = 19.4607 (10) Å | Cell parameters from 25 reflections |
b = 10.5889 (15) Å | θ = 16.4–19.1° |
c = 9.0394 (12) Å | µ = 0.07 mm−1 |
β = 99.948 (8)° | T = 296 K |
V = 1834.7 (4) Å3 | Prism, colorless |
Z = 4 | 0.43 × 0.33 × 0.19 mm |
Data collection top
Rigaku AFC-5S diffractometer | Rint = 0.031 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.1° |
Graphite monochromator | h = −23→22 |
ω scans | k = −12→0 |
3484 measured reflections | l = 0→10 |
3254 independent reflections | 3 standard reflections every 100 reflections |
1521 reflections with I > 2σ(I) | intensity decay: 0.3% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-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 reflections | Δρmax = 0.14 e Å−3 |
210 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0107 (15) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.59118 (8) | 0.07179 (16) | 0.29843 (19) | 0.0760 (5) | |
N1 | 0.41999 (8) | 0.22685 (15) | 0.43220 (18) | 0.0462 (5) | |
C2 | 0.48216 (11) | 0.2893 (2) | 0.4530 (2) | 0.0532 (6) | |
C3 | 0.53938 (11) | 0.2407 (2) | 0.4103 (3) | 0.0584 (6) | |
C4 | 0.53893 (11) | 0.1190 (2) | 0.3396 (2) | 0.0519 (6) | |
C5 | 0.47250 (11) | 0.0590 (2) | 0.3201 (2) | 0.0570 (6) | |
C6 | 0.41675 (11) | 0.1115 (2) | 0.3641 (2) | 0.0543 (6) | |
C7 | 0.35833 (10) | 0.27903 (18) | 0.4769 (2) | 0.0439 (5) | |
C8 | 0.32023 (10) | 0.2052 (2) | 0.5590 (2) | 0.0488 (5) | |
C9 | 0.25768 (10) | 0.2499 (2) | 0.5912 (2) | 0.0511 (6) | |
C10 | 0.23259 (10) | 0.36793 (19) | 0.5447 (2) | 0.0462 (5) | |
C11 | 0.27377 (11) | 0.44196 (19) | 0.4680 (2) | 0.0520 (6) | |
C12 | 0.33614 (11) | 0.39931 (19) | 0.4334 (2) | 0.0501 (6) | |
C13 | 0.16199 (10) | 0.4161 (2) | 0.5673 (3) | 0.0581 (6) | |
C14 | 0.12702 (10) | 0.3496 (2) | 0.6822 (2) | 0.0538 (6) | |
C15 | 0.05615 (10) | 0.4052 (2) | 0.6940 (2) | 0.0568 (6) | |
C16 | 0.02081 (10) | 0.3437 (2) | 0.8118 (2) | 0.0559 (6) | |
C17 | −0.04975 (10) | 0.3998 (2) | 0.8233 (2) | 0.0560 (6) | |
C18 | −0.08488 (10) | 0.3394 (2) | 0.9428 (2) | 0.0546 (6) | |
C19 | −0.15511 (10) | 0.3955 (2) | 0.9567 (2) | 0.0544 (6) | |
C20 | −0.19051 (10) | 0.3315 (2) | 1.0729 (2) | 0.0535 (6) | |
C21 | −0.26111 (10) | 0.3852 (2) | 1.0866 (3) | 0.0600 (6) | |
C22 | −0.29699 (12) | 0.3173 (2) | 1.1990 (3) | 0.0718 (7) | |
H2 | 0.4850 | 0.3684 | 0.4984 | 0.064* | |
H3 | 0.5806 | 0.2872 | 0.4270 | 0.070* | |
H5 | 0.4676 | −0.0201 | 0.2747 | 0.068* | |
H6 | 0.3746 | 0.0680 | 0.3477 | 0.065* | |
H8 | 0.3365 | 0.1259 | 0.5926 | 0.059* | |
H9 | 0.2319 | 0.1992 | 0.6455 | 0.061* | |
H11 | 0.2588 | 0.5231 | 0.4389 | 0.062* | |
H12 | 0.3627 | 0.4507 | 0.3818 | 0.060* | |
H13A | 0.1670 | 0.5045 | 0.5954 | 0.070* | |
H13B | 0.1308 | 0.4121 | 0.4714 | 0.070* | |
H14A | 0.1570 | 0.3548 | 0.7796 | 0.065* | |
H14B | 0.1213 | 0.2611 | 0.6555 | 0.065* | |
H15A | 0.0618 | 0.4945 | 0.7166 | 0.068* | |
H15B | 0.0259 | 0.3974 | 0.5971 | 0.068* | |
H16A | 0.0511 | 0.3513 | 0.9087 | 0.067* | |
H16B | 0.0149 | 0.2545 | 0.7890 | 0.067* | |
H17A | −0.0439 | 0.4893 | 0.8448 | 0.067* | |
H17B | −0.0802 | 0.3913 | 0.7268 | 0.067* | |
H18A | −0.0910 | 0.2501 | 0.9207 | 0.066* | |
H18B | −0.0541 | 0.3471 | 1.0390 | 0.066* | |
H19A | −0.1488 | 0.4842 | 0.9823 | 0.065* | |
H19B | −0.1855 | 0.3903 | 0.8598 | 0.065* | |
H20A | −0.1960 | 0.2426 | 1.0481 | 0.064* | |
H20B | −0.1603 | 0.3379 | 1.1699 | 0.064* | |
H21A | −0.2555 | 0.4733 | 1.1154 | 0.072* | |
H21B | −0.2909 | 0.3818 | 0.9889 | 0.072* | |
H22A | −0.3016 | 0.2294 | 1.1732 | 0.108* | |
H22B | −0.3424 | 0.3532 | 1.1975 | 0.108* | |
H22C | −0.2698 | 0.3262 | 1.2976 | 0.108* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0633 (10) | 0.0800 (13) | 0.0931 (13) | 0.0186 (9) | 0.0375 (9) | −0.0015 (10) |
N1 | 0.0451 (10) | 0.0452 (11) | 0.0515 (11) | −0.0007 (8) | 0.0177 (8) | −0.0037 (9) |
C2 | 0.0548 (14) | 0.0457 (13) | 0.0619 (15) | −0.0066 (11) | 0.0186 (11) | −0.0065 (11) |
C3 | 0.0505 (13) | 0.0573 (14) | 0.0712 (17) | −0.0031 (12) | 0.0210 (12) | −0.0014 (13) |
C4 | 0.0546 (13) | 0.0543 (14) | 0.0503 (14) | 0.0112 (12) | 0.0187 (11) | 0.0084 (11) |
C5 | 0.0608 (15) | 0.0494 (14) | 0.0636 (15) | 0.0061 (12) | 0.0187 (12) | −0.0124 (11) |
C6 | 0.0551 (13) | 0.0454 (13) | 0.0645 (15) | −0.0040 (11) | 0.0161 (11) | −0.0126 (12) |
C7 | 0.0474 (12) | 0.0433 (13) | 0.0441 (12) | 0.0016 (10) | 0.0165 (10) | −0.0053 (10) |
C8 | 0.0523 (13) | 0.0416 (12) | 0.0557 (13) | 0.0034 (10) | 0.0178 (10) | 0.0063 (10) |
C9 | 0.0527 (13) | 0.0469 (13) | 0.0586 (14) | −0.0027 (11) | 0.0235 (11) | 0.0070 (11) |
C10 | 0.0512 (13) | 0.0434 (13) | 0.0469 (13) | 0.0032 (10) | 0.0166 (10) | −0.0006 (10) |
C11 | 0.0632 (14) | 0.0412 (12) | 0.0562 (14) | 0.0081 (11) | 0.0233 (12) | 0.0053 (11) |
C12 | 0.0614 (14) | 0.0427 (12) | 0.0520 (14) | −0.0020 (11) | 0.0255 (11) | 0.0005 (10) |
C13 | 0.0543 (14) | 0.0570 (15) | 0.0673 (16) | 0.0073 (11) | 0.0226 (11) | 0.0035 (12) |
C14 | 0.0499 (13) | 0.0579 (14) | 0.0562 (14) | 0.0013 (11) | 0.0167 (11) | 0.0008 (11) |
C15 | 0.0494 (13) | 0.0607 (15) | 0.0628 (15) | 0.0025 (12) | 0.0172 (11) | −0.0007 (12) |
C16 | 0.0474 (13) | 0.0615 (15) | 0.0603 (15) | 0.0003 (11) | 0.0132 (10) | −0.0004 (12) |
C17 | 0.0449 (12) | 0.0607 (15) | 0.0645 (16) | −0.0002 (11) | 0.0158 (11) | −0.0007 (12) |
C18 | 0.0453 (13) | 0.0610 (15) | 0.0592 (15) | −0.0004 (11) | 0.0136 (11) | 0.0004 (12) |
C19 | 0.0434 (12) | 0.0574 (14) | 0.0628 (15) | −0.0016 (11) | 0.0106 (10) | 0.0007 (12) |
C20 | 0.0461 (13) | 0.0538 (14) | 0.0614 (14) | 0.0007 (10) | 0.0115 (11) | 0.0017 (11) |
C21 | 0.0482 (13) | 0.0626 (15) | 0.0714 (16) | 0.0033 (12) | 0.0164 (11) | 0.0036 (13) |
C22 | 0.0591 (15) | 0.0715 (17) | 0.092 (2) | 0.0040 (13) | 0.0324 (14) | 0.0105 (15) |
Geometric parameters (Å, º) top
O1—C4 | 1.247 (2) | C6—H6 | 0.9300 |
N1—C2 | 1.363 (2) | C8—H8 | 0.9300 |
N1—C6 | 1.365 (4) | C9—H9 | 0.9300 |
N1—C7 | 1.441 (2) | C11—H11 | 0.9300 |
C7—C12 | 1.380 (3) | C12—H12 | 0.9300 |
C7—C8 | 1.379 (3) | C13—H13A | 0.9700 |
C2—C3 | 1.342 (3) | C13—H13B | 0.9700 |
C3—C4 | 1.438 (4) | C14—H14A | 0.9700 |
C4—C5 | 1.424 (3) | C14—H14B | 0.9700 |
C5—C6 | 1.339 (3) | C15—H15A | 0.9700 |
C8—C9 | 1.383 (3) | C15—H15B | 0.9700 |
C9—C10 | 1.381 (3) | C16—H16A | 0.9700 |
C10—C11 | 1.389 (3) | C16—H16B | 0.9700 |
C11—C12 | 1.381 (3) | C17—H17A | 0.9700 |
C10—C13 | 1.512 (3) | C17—H17B | 0.9700 |
C13—C14 | 1.510 (4) | C18—H18A | 0.9700 |
C14—C15 | 1.520 (3) | C18—H18B | 0.9700 |
C15—C16 | 1.512 (4) | C19—H19A | 0.9700 |
C16—C17 | 1.516 (3) | C19—H19B | 0.9700 |
C17—C18 | 1.516 (4) | C20—H20A | 0.9700 |
C18—C19 | 1.515 (3) | C20—H20B | 0.9700 |
C19—C20 | 1.513 (4) | C21—H21A | 0.9700 |
C20—C21 | 1.511 (3) | C21—H21B | 0.9700 |
C21—C22 | 1.510 (4) | C22—H22A | 0.9600 |
C2—H2 | 0.9300 | C22—H22B | 0.9600 |
C3—H3 | 0.9300 | C22—H22C | 0.9600 |
C5—H5 | 0.9300 | | |
| | | |
C2—N1—C6 | 117.87 (18) | C10—C13—H13B | 107.9 |
C2—N1—C7 | 122.5 (2) | H13A—C13—H13B | 107.2 |
C6—N1—C7 | 119.62 (18) | C13—C14—H14A | 109.0 |
C3—C2—N1 | 122.3 (2) | C15—C14—H14A | 109.0 |
C2—C3—C4 | 122.0 (2) | C13—C14—H14B | 109.0 |
O1—C4—C5 | 123.6 (2) | C15—C14—H14B | 109.0 |
O1—C4—C3 | 123.4 (2) | H14A—C14—H14B | 107.8 |
C5—C4—C3 | 113.03 (19) | C16—C15—H15A | 108.7 |
C6—C5—C4 | 122.8 (2) | C14—C15—H15A | 108.7 |
C5—C6—N1 | 121.9 (2) | C16—C15—H15B | 108.7 |
C8—C7—C12 | 120.4 (2) | C14—C15—H15B | 108.7 |
C8—C7—N1 | 119.00 (18) | H15A—C15—H15B | 107.6 |
C12—C7—N1 | 120.58 (19) | C15—C16—H16A | 108.7 |
C7—C8—C9 | 119.6 (2) | C17—C16—H16A | 108.7 |
C10—C9—C8 | 121.5 (2) | C15—C16—H16B | 108.7 |
C9—C10—C11 | 117.3 (2) | C17—C16—H16B | 108.7 |
C9—C10—C13 | 123.08 (19) | H16A—C16—H16B | 107.6 |
C11—C10—C13 | 119.5 (2) | C18—C17—H17A | 108.7 |
C12—C11—C10 | 122.3 (2) | C16—C17—H17A | 108.7 |
C7—C12—C11 | 118.8 (2) | C18—C17—H17B | 108.7 |
C14—C13—C10 | 117.6 (2) | C16—C17—H17B | 108.7 |
C13—C14—C15 | 112.9 (2) | H17A—C17—H17B | 107.6 |
C16—C15—C14 | 114.3 (2) | C19—C18—H18A | 108.6 |
C15—C16—C17 | 114.0 (2) | C17—C18—H18A | 108.6 |
C18—C17—C16 | 114.1 (2) | C19—C18—H18B | 108.6 |
C19—C18—C17 | 114.7 (2) | C17—C18—H18B | 108.6 |
C20—C19—C18 | 114.0 (2) | H18A—C18—H18B | 107.6 |
C21—C20—C19 | 114.7 (2) | C20—C19—H19A | 108.7 |
C22—C21—C20 | 114.1 (2) | C18—C19—H19A | 108.7 |
C3—C2—H2 | 118.8 | C20—C19—H19B | 108.7 |
N1—C2—H2 | 118.8 | C18—C19—H19B | 108.7 |
C2—C3—H3 | 119.0 | H19A—C19—H19B | 107.6 |
C4—C3—H3 | 119.0 | C21—C20—H20A | 108.6 |
C6—C5—H5 | 118.6 | C19—C20—H20A | 108.6 |
C4—C5—H5 | 118.6 | C21—C20—H20B | 108.6 |
C5—C6—H6 | 119.0 | C19—C20—H20B | 108.6 |
N1—C6—H6 | 119.0 | H20A—C20—H20B | 107.6 |
C7—C8—H8 | 120.2 | C22—C21—H21A | 108.7 |
C9—C8—H8 | 120.2 | C20—C21—H21A | 108.7 |
C10—C9—H9 | 119.2 | C22—C21—H21B | 108.7 |
C8—C9—H9 | 119.2 | C20—C21—H21B | 108.7 |
C7—C12—H12 | 120.6 | H21A—C21—H21B | 107.6 |
C11—C12—H12 | 120.6 | C21—C22—H22A | 109.5 |
C12—C11—H11 | 118.9 | C21—C22—H22B | 109.5 |
C10—C11—H11 | 118.9 | H22A—C22—H22B | 109.5 |
C14—C13—H13A | 107.9 | C21—C22—H22C | 109.5 |
C10—C13—H13A | 107.9 | H22A—C22—H22C | 109.5 |
C14—C13—H13B | 107.9 | H22B—C22—H22C | 109.5 |
| | | |
C6—N1—C2—C3 | −0.6 (3) | C8—C9—C10—C11 | −1.9 (3) |
C7—N1—C2—C3 | −179.6 (2) | C8—C9—C10—C13 | 175.2 (2) |
N1—C2—C3—C4 | −0.1 (3) | C9—C10—C11—C12 | 2.4 (3) |
C2—C3—C4—O1 | 179.8 (2) | C13—C10—C11—C12 | −174.8 (2) |
C2—C3—C4—C5 | 0.5 (3) | C8—C7—C12—C11 | −2.8 (3) |
O1—C4—C5—C6 | −179.5 (2) | N1—C7—C12—C11 | 174.71 (19) |
C3—C4—C5—C6 | −0.2 (3) | C10—C11—C12—C7 | −0.1 (3) |
C4—C5—C6—N1 | −0.4 (4) | C9—C10—C13—C14 | 17.8 (3) |
C2—N1—C6—C5 | 0.9 (3) | C11—C10—C13—C14 | −165.1 (2) |
C7—N1—C6—C5 | 179.8 (2) | C10—C13—C14—C15 | −179.38 (19) |
C2—N1—C7—C8 | −131.3 (2) | C13—C14—C15—C16 | −177.98 (19) |
C6—N1—C7—C8 | 49.7 (3) | C14—C15—C16—C17 | 179.83 (18) |
C2—N1—C7—C12 | 51.2 (3) | C15—C16—C17—C18 | −179.26 (18) |
C6—N1—C7—C12 | −127.8 (2) | C16—C17—C18—C19 | 179.39 (19) |
C12—C7—C8—C9 | 3.3 (3) | C17—C18—C19—C20 | 178.16 (19) |
N1—C7—C8—C9 | −174.25 (19) | C18—C19—C20—C21 | −179.17 (19) |
C7—C8—C9—C10 | −0.9 (3) | C19—C20—C21—C22 | 177.86 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O1i | 0.93 | 2.37 | 3.279 (3) | 166 |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |