Methyl 3-benzoyl-3-(6-methyl-2-pyridyl)-2-phenyl­acryl­ate

The benzoyl and phenyl rings of the title mol­ecule, C₂₃H₁₉NO₃, 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.

Key indicators

• Single-crystal X-ray study
• T = 213 K
• Mean [sigma](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

---

Computing details

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

Crystal data

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) Å^3	Needle, colorless
Z = 4	0.38 × 0.14 × 0.12 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.062	H-atom parameters constrained
wR(F^2) = 0.148	w = 1/[σ^2(Fo^2) + (0.0303P)^2] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (2)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1^i	0.93	2.56	3.170 (5)	124

Symmetry code: (i) x−1, y, z.