The benzoyl and phenyl rings of the title molecule, C
23H
19NO
3, are oriented at angles of 79.9 (1) and 70.8 (1)°, respectively, with respect to the pyridine ring. The weak C—H
O intermolecular hydrogen bonds link the molecules to form infinite one-dimensional chains along the
a-axis direction.
Supporting information
CCDC reference: 189915
Key indicators
- Single-crystal X-ray study
- T = 213 K
- Mean (C-C) = 0.005 Å
- R factor = 0.062
- wR factor = 0.148
- Data-to-parameter ratio = 13.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
RINTA_01 Alert C The value of Rint is greater than 0.10
Rint given 0.119
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
Methyl 3-benzoyl-3-(6-methyl-2-pyridyl)-2-phenylacrylate
top
Crystal data top
C23H19NO3 | F(000) = 752 |
Mr = 357.39 | Dx = 1.276 Mg m−3 |
Monoclinic, P21/n | Melting point: 412(1) K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 8.6711 (3) Å | Cell parameters from 3918 reflections |
b = 23.2413 (7) Å | θ = 2.7–28.3° |
c = 10.0129 (3) Å | µ = 0.09 mm−1 |
β = 112.744 (1)° | T = 213 K |
V = 1861.0 (1) Å3 | Needle, colorless |
Z = 4 | 0.38 × 0.14 × 0.12 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 1711 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.119 |
Graphite monochromator | θmax = 25.0°, θmin = 2.7° |
Detector resolution: 8.33 pixels mm-1 | h = −10→10 |
ω scans | k = −26→27 |
8684 measured reflections | l = −7→11 |
3233 independent reflections | |
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)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.148 | w = 1/[σ2(Fo2) + (0.0303P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.84 | (Δ/σ)max < 0.001 |
3233 reflections | Δρmax = 0.23 e Å−3 |
247 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.024 (2) |
Special details top
Experimental. The data collection covered over a hemisphere of reciprocal space by a
combination of three sets of exposures; each set had a different φ angle (0,
88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω.
The crystal-to-detector distance was 4 cm and the detector swing angle was
-35°. Crystal decay was monitored by repeating fifty initial frames at the
end of data collection and analysing the intensity of duplicate reflections,
and was found to be negligible. |
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 | x | y | z | Uiso*/Ueq | |
O1 | 1.0732 (3) | 0.12247 (9) | 0.5843 (2) | 0.0400 (6) | |
O2 | 1.0097 (3) | 0.22022 (11) | 0.3545 (3) | 0.0654 (9) | |
O3 | 1.0908 (3) | 0.28591 (10) | 0.5262 (2) | 0.0470 (7) | |
N1 | 0.7202 (3) | 0.09765 (10) | 0.6152 (2) | 0.0273 (6) | |
C1 | 0.9436 (5) | 0.04537 (13) | 0.3525 (4) | 0.0418 (9) | |
H1 | 1.0475 | 0.0370 | 0.4242 | 0.050* | |
C2 | 0.8776 (6) | 0.01026 (16) | 0.2324 (4) | 0.0582 (11) | |
H2 | 0.9361 | −0.0221 | 0.2237 | 0.070* | |
C3 | 0.7243 (6) | 0.02346 (18) | 0.1251 (5) | 0.0623 (13) | |
H3 | 0.6804 | 0.0000 | 0.0439 | 0.075* | |
C4 | 0.6359 (5) | 0.07110 (17) | 0.1372 (4) | 0.0527 (10) | |
H4 | 0.5332 | 0.0798 | 0.0642 | 0.063* | |
C5 | 0.7010 (4) | 0.10606 (13) | 0.2589 (3) | 0.0347 (8) | |
H5 | 0.6415 | 0.1380 | 0.2685 | 0.042* | |
C6 | 0.8556 (4) | 0.09285 (12) | 0.3663 (3) | 0.0260 (7) | |
C7 | 0.9296 (4) | 0.12938 (12) | 0.4983 (3) | 0.0239 (7) | |
C8 | 0.8230 (3) | 0.17657 (12) | 0.5243 (3) | 0.0206 (7) | |
C9 | 0.6917 (3) | 0.15311 (12) | 0.5720 (3) | 0.0234 (7) | |
C10 | 0.5535 (4) | 0.18288 (13) | 0.5692 (3) | 0.0306 (8) | |
H10 | 0.5372 | 0.2212 | 0.5400 | 0.037* | |
C11 | 0.4393 (4) | 0.15448 (14) | 0.6108 (3) | 0.0388 (8) | |
H11 | 0.3447 | 0.1736 | 0.6099 | 0.047* | |
C12 | 0.4659 (4) | 0.09834 (14) | 0.6533 (3) | 0.0362 (8) | |
H12 | 0.3890 | 0.0789 | 0.6806 | 0.043* | |
C13 | 0.6079 (4) | 0.07062 (13) | 0.6553 (3) | 0.0321 (8) | |
C14 | 0.8581 (3) | 0.23163 (12) | 0.5078 (3) | 0.0213 (7) | |
C15 | 0.7722 (3) | 0.28346 (12) | 0.5338 (3) | 0.0229 (7) | |
C16 | 0.6704 (4) | 0.31575 (13) | 0.4169 (3) | 0.0315 (8) | |
H16 | 0.6572 | 0.3051 | 0.3236 | 0.038* | |
C17 | 0.5878 (4) | 0.36393 (13) | 0.4378 (4) | 0.0374 (8) | |
H17 | 0.5174 | 0.3848 | 0.3584 | 0.045* | |
C18 | 0.6097 (4) | 0.38081 (13) | 0.5752 (4) | 0.0395 (9) | |
H18 | 0.5539 | 0.4131 | 0.5888 | 0.047* | |
C19 | 0.7142 (4) | 0.35011 (14) | 0.6933 (4) | 0.0402 (9) | |
H19 | 0.7305 | 0.3621 | 0.7864 | 0.048* | |
C20 | 0.7949 (4) | 0.30142 (13) | 0.6731 (3) | 0.0320 (8) | |
H20 | 0.8647 | 0.2806 | 0.7529 | 0.038* | |
C21 | 0.9925 (4) | 0.24412 (13) | 0.4525 (3) | 0.0269 (7) | |
C22 | 1.2288 (4) | 0.30254 (15) | 0.4871 (4) | 0.0451 (9) | |
H22A | 1.3233 | 0.3128 | 0.5728 | 0.068* | |
H22B | 1.1963 | 0.3349 | 0.4226 | 0.068* | |
H22C | 1.2582 | 0.2709 | 0.4399 | 0.068* | |
C23 | 0.6461 (5) | 0.00890 (14) | 0.7006 (4) | 0.0530 (10) | |
H23A | 0.6844 | −0.0104 | 0.6344 | 0.080* | |
H23B | 0.5468 | −0.0096 | 0.6998 | 0.080* | |
H23C | 0.7315 | 0.0073 | 0.7964 | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0213 (13) | 0.0441 (15) | 0.0510 (15) | 0.0060 (11) | 0.0101 (11) | −0.0020 (11) |
O2 | 0.087 (2) | 0.0690 (19) | 0.0725 (19) | −0.0431 (15) | 0.0666 (17) | −0.0387 (15) |
O3 | 0.0383 (14) | 0.0564 (16) | 0.0615 (16) | −0.0294 (12) | 0.0360 (12) | −0.0299 (12) |
N1 | 0.0288 (15) | 0.0244 (15) | 0.0313 (14) | −0.0001 (12) | 0.0143 (12) | 0.0040 (11) |
C1 | 0.055 (2) | 0.0259 (19) | 0.056 (2) | 0.0010 (17) | 0.0345 (18) | −0.0020 (16) |
C2 | 0.081 (3) | 0.035 (2) | 0.080 (3) | −0.011 (2) | 0.055 (3) | −0.020 (2) |
C3 | 0.095 (4) | 0.051 (3) | 0.061 (3) | −0.040 (3) | 0.052 (3) | −0.027 (2) |
C4 | 0.063 (3) | 0.052 (3) | 0.039 (2) | −0.024 (2) | 0.0147 (18) | −0.0089 (18) |
C5 | 0.035 (2) | 0.0325 (19) | 0.0367 (19) | −0.0078 (16) | 0.0137 (15) | −0.0061 (14) |
C6 | 0.0302 (18) | 0.0211 (16) | 0.0348 (18) | −0.0043 (14) | 0.0214 (14) | −0.0004 (13) |
C7 | 0.0206 (17) | 0.0232 (17) | 0.0315 (17) | −0.0014 (14) | 0.0140 (14) | 0.0040 (13) |
C8 | 0.0169 (16) | 0.0251 (17) | 0.0189 (15) | −0.0001 (13) | 0.0060 (12) | −0.0020 (12) |
C9 | 0.0207 (16) | 0.0268 (17) | 0.0193 (15) | −0.0008 (14) | 0.0040 (12) | −0.0018 (12) |
C10 | 0.0231 (18) | 0.0290 (18) | 0.0401 (19) | 0.0033 (15) | 0.0126 (15) | 0.0033 (14) |
C11 | 0.0276 (19) | 0.039 (2) | 0.054 (2) | 0.0056 (16) | 0.0212 (16) | 0.0042 (16) |
C12 | 0.0256 (19) | 0.046 (2) | 0.041 (2) | −0.0030 (16) | 0.0172 (15) | 0.0043 (16) |
C13 | 0.0304 (19) | 0.0299 (18) | 0.0361 (19) | −0.0026 (15) | 0.0130 (15) | 0.0054 (14) |
C14 | 0.0211 (17) | 0.0250 (17) | 0.0183 (15) | 0.0012 (13) | 0.0080 (12) | −0.0002 (12) |
C15 | 0.0229 (17) | 0.0198 (16) | 0.0281 (17) | −0.0007 (13) | 0.0123 (13) | 0.0001 (13) |
C16 | 0.035 (2) | 0.0328 (19) | 0.0255 (17) | −0.0022 (15) | 0.0105 (14) | 0.0024 (14) |
C17 | 0.033 (2) | 0.0247 (18) | 0.051 (2) | 0.0029 (15) | 0.0119 (16) | 0.0078 (15) |
C18 | 0.037 (2) | 0.0201 (18) | 0.066 (3) | 0.0022 (16) | 0.0252 (18) | −0.0052 (17) |
C19 | 0.049 (2) | 0.036 (2) | 0.043 (2) | −0.0046 (18) | 0.0255 (17) | −0.0110 (16) |
C20 | 0.033 (2) | 0.0318 (19) | 0.0305 (18) | 0.0029 (15) | 0.0115 (14) | 0.0006 (14) |
C21 | 0.0317 (19) | 0.0223 (17) | 0.0291 (17) | −0.0019 (14) | 0.0145 (14) | 0.0021 (14) |
C22 | 0.039 (2) | 0.044 (2) | 0.064 (2) | −0.0126 (17) | 0.0330 (19) | −0.0075 (17) |
C23 | 0.058 (3) | 0.033 (2) | 0.082 (3) | 0.0004 (19) | 0.042 (2) | 0.0188 (19) |
Geometric parameters (Å, º) top
O1—C7 | 1.220 (3) | C11—C12 | 1.364 (4) |
O2—C21 | 1.186 (3) | C11—H11 | 0.93 |
O3—C21 | 1.315 (3) | C12—C13 | 1.383 (4) |
O3—C22 | 1.448 (4) | C12—H12 | 0.93 |
N1—C13 | 1.344 (4) | C13—C23 | 1.502 (4) |
N1—C9 | 1.352 (3) | C14—C15 | 1.491 (4) |
C1—C6 | 1.379 (4) | C14—C21 | 1.499 (4) |
C1—C2 | 1.381 (5) | C15—C16 | 1.383 (4) |
C1—H1 | 0.93 | C15—C20 | 1.395 (4) |
C2—C3 | 1.382 (5) | C16—C17 | 1.388 (4) |
C2—H2 | 0.93 | C16—H16 | 0.93 |
C3—C4 | 1.379 (5) | C17—C18 | 1.372 (4) |
C3—H3 | 0.93 | C17—H17 | 0.93 |
C4—C5 | 1.390 (4) | C18—C19 | 1.378 (4) |
C4—H4 | 0.93 | C18—H18 | 0.93 |
C5—C6 | 1.390 (4) | C19—C20 | 1.386 (4) |
C5—H5 | 0.93 | C19—H19 | 0.93 |
C6—C7 | 1.491 (4) | C20—H20 | 0.93 |
C7—C8 | 1.520 (4) | C22—H22A | 0.96 |
C8—C14 | 1.340 (4) | C22—H22B | 0.96 |
C8—C9 | 1.497 (4) | C22—H22C | 0.96 |
C9—C10 | 1.375 (4) | C23—H23A | 0.96 |
C10—C11 | 1.381 (4) | C23—H23B | 0.96 |
C10—H10 | 0.93 | C23—H23C | 0.96 |
| | | |
C21—O3—C22 | 118.0 (2) | N1—C13—C23 | 115.8 (3) |
C13—N1—C9 | 118.5 (3) | C12—C13—C23 | 122.7 (3) |
C6—C1—C2 | 120.1 (4) | C8—C14—C15 | 126.7 (3) |
C6—C1—H1 | 120.0 | C8—C14—C21 | 118.4 (2) |
C2—C1—H1 | 120.0 | C15—C14—C21 | 114.8 (2) |
C1—C2—C3 | 119.7 (4) | C16—C15—C20 | 118.7 (3) |
C1—C2—H2 | 120.1 | C16—C15—C14 | 119.3 (3) |
C3—C2—H2 | 120.1 | C20—C15—C14 | 122.0 (2) |
C4—C3—C2 | 120.7 (4) | C15—C16—C17 | 120.6 (3) |
C4—C3—H3 | 119.7 | C15—C16—H16 | 119.7 |
C2—C3—H3 | 119.7 | C17—C16—H16 | 119.7 |
C3—C4—C5 | 119.7 (4) | C18—C17—C16 | 120.1 (3) |
C3—C4—H4 | 120.2 | C18—C17—H17 | 119.9 |
C5—C4—H4 | 120.2 | C16—C17—H17 | 119.9 |
C6—C5—C4 | 119.5 (3) | C17—C18—C19 | 120.2 (3) |
C6—C5—H5 | 120.3 | C17—C18—H18 | 119.9 |
C4—C5—H5 | 120.3 | C19—C18—H18 | 119.9 |
C1—C6—C5 | 120.3 (3) | C18—C19—C20 | 120.0 (3) |
C1—C6—C7 | 118.6 (3) | C18—C19—H19 | 120.0 |
C5—C6—C7 | 121.0 (3) | C20—C19—H19 | 120.0 |
O1—C7—C6 | 121.5 (3) | C19—C20—C15 | 120.4 (3) |
O1—C7—C8 | 119.8 (3) | C19—C20—H20 | 119.8 |
C6—C7—C8 | 118.8 (2) | C15—C20—H20 | 119.8 |
C14—C8—C9 | 128.6 (3) | O2—C21—O3 | 123.3 (3) |
C14—C8—C7 | 119.1 (2) | O2—C21—C14 | 125.4 (3) |
C9—C8—C7 | 112.3 (2) | O3—C21—C14 | 111.3 (3) |
N1—C9—C10 | 122.4 (3) | O3—C22—H22A | 109.5 |
N1—C9—C8 | 112.5 (2) | O3—C22—H22B | 109.5 |
C10—C9—C8 | 125.1 (3) | H22A—C22—H22B | 109.5 |
C9—C10—C11 | 118.3 (3) | O3—C22—H22C | 109.5 |
C9—C10—H10 | 120.8 | H22A—C22—H22C | 109.5 |
C11—C10—H10 | 120.8 | H22B—C22—H22C | 109.5 |
C12—C11—C10 | 119.8 (3) | C13—C23—H23A | 109.5 |
C12—C11—H11 | 120.1 | C13—C23—H23B | 109.5 |
C10—C11—H11 | 120.1 | H23A—C23—H23B | 109.5 |
C11—C12—C13 | 119.5 (3) | C13—C23—H23C | 109.5 |
C11—C12—H12 | 120.3 | H23A—C23—H23C | 109.5 |
C13—C12—H12 | 120.3 | H23B—C23—H23C | 109.5 |
N1—C13—C12 | 121.4 (3) | | |
| | | |
C6—C1—C2—C3 | 1.0 (5) | C9—N1—C13—C12 | −0.1 (4) |
C1—C2—C3—C4 | −0.5 (6) | C9—N1—C13—C23 | 179.3 (3) |
C2—C3—C4—C5 | −0.4 (5) | C11—C12—C13—N1 | −0.5 (5) |
C3—C4—C5—C6 | 0.8 (5) | C11—C12—C13—C23 | −180.0 (3) |
C2—C1—C6—C5 | −0.7 (5) | C9—C8—C14—C15 | 0.0 (4) |
C2—C1—C6—C7 | 179.2 (3) | C7—C8—C14—C15 | −177.5 (2) |
C4—C5—C6—C1 | −0.2 (5) | C9—C8—C14—C21 | −177.5 (3) |
C4—C5—C6—C7 | 179.9 (3) | C7—C8—C14—C21 | 4.9 (4) |
C1—C6—C7—O1 | 9.3 (4) | C8—C14—C15—C16 | −109.1 (3) |
C5—C6—C7—O1 | −170.8 (3) | C21—C14—C15—C16 | 68.5 (4) |
C1—C6—C7—C8 | −171.4 (3) | C8—C14—C15—C20 | 72.7 (4) |
C5—C6—C7—C8 | 8.5 (4) | C21—C14—C15—C20 | −109.7 (3) |
O1—C7—C8—C14 | 71.0 (3) | C20—C15—C16—C17 | −2.3 (4) |
C6—C7—C8—C14 | −108.3 (3) | C14—C15—C16—C17 | 179.5 (3) |
O1—C7—C8—C9 | −106.9 (3) | C15—C16—C17—C18 | 1.6 (5) |
C6—C7—C8—C9 | 73.8 (3) | C16—C17—C18—C19 | 0.2 (5) |
C13—N1—C9—C10 | 0.7 (4) | C17—C18—C19—C20 | −1.2 (5) |
C13—N1—C9—C8 | −177.4 (2) | C18—C19—C20—C15 | 0.5 (5) |
C14—C8—C9—N1 | −162.7 (3) | C16—C15—C20—C19 | 1.2 (4) |
C7—C8—C9—N1 | 15.0 (3) | C14—C15—C20—C19 | 179.4 (3) |
C14—C8—C9—C10 | 19.2 (4) | C22—O3—C21—O2 | −1.3 (5) |
C7—C8—C9—C10 | −163.1 (3) | C22—O3—C21—C14 | 179.1 (3) |
N1—C9—C10—C11 | −0.7 (4) | C8—C14—C21—O2 | 44.2 (5) |
C8—C9—C10—C11 | 177.2 (3) | C15—C14—C21—O2 | −133.7 (3) |
C9—C10—C11—C12 | 0.0 (5) | C8—C14—C21—O3 | −136.3 (3) |
C10—C11—C12—C13 | 0.6 (5) | C15—C14—C21—O3 | 45.9 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O1i | 0.93 | 2.56 | 3.170 (5) | 124 |
Symmetry code: (i) x−1, y, z. |