1,5-Diphenyl-3-(2-pyrid­yl)pentane-1,5-dione

Huang, X.-Q.; Wang, D.-Q.; Dou, J.-M.; Wang, J.-X.

doi:10.1107/S1600536805040080

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1,5-Diphenyl-3-(2-pyridyl)pentane-1,5-dione

X.-Q. Huang, D.-Q. Wang, J.-M. Dou and J.-X. Wang

The title compund, C₂₂H₁₉NO₂, was synthesized by the reaction of pyridine-2-carbaldehyde with acetophenone and NaOH. The bond lengths and angles show normal values. The crystal packing exhibits no significantly short intermolecular contacts.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040080/cv6614sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040080/cv6614Isup2.hkl Contains datablock I

CCDC reference: 280717

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R factor = 0.045
wR factor = 0.128
Data-to-parameter ratio = 14.0

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 .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.72 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   1 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

Comment top

Organic syntheses directed towards `green' chemistry have attracted increasing interest in recent years in view of expectations of new enviromentally benign procedures saving resources and energy (Tanaka & Toda, 2000; Dittmer, 1997). The development of solvent-free reactions (DeSimone, 2002; Cave et al., 2001; Tanaka, 2003) is an especially attractive goal in the context of green chemistry (Anastas & Kirchhoff, 2002). 1,5-Diketones are important synthetic intermediates and starting materials in the synthesis of many heterocyclic compounds (Hirsch & Bailey, 1978; Krohnke, 1976). It is also known that pyridine-containing compounds often exhibit strong biological activity (Keys et al., 1987). In continuation of work on the synthesis of 1,5-diketones (Constable et al., 1998; Fuchigami et al., 1986), we present here the title new pyridine-containing compound, (I), synthesized under solvent-free conditions.

In the molecule of (I) (Fig. 1), the bond lengths and angles (Table 1) are normal and correspond to those observed in 1,3,5-triphenylpentane-1,5-diketone (Das et al., 1994). The crystal packing (Fig. 2) demonstrates no significantly short intermolecular contacts.

Experimental top

Pyridine-2-carboxaldehyde was used as obtained with no further purification. Acetophenone (0.75 g, 6.25 mmol), freshly distilled [Please clarify - contradicts first sentence] pyridine-2-carboxaldehyde (0.33 g, 3.125 mmol) and NaOH (0.25 g, 6.25 mmol) were aggregated using a glass paddle in an open flask. The resulting mixture was washed with water several times to remove NaOH, and then recrystallized from ethanol (m.p. 424 K). EI—MS (m/e, %): 329 (1.62), 252 (13.14), 224(45.88), 210(11.1), 105 (100), 77(69.45); ¹H NMR (400 MHz, CDCl₃, δ, p.p.m.): 8.45–7.01 (m, 14H), 4.24–4.17 (m, J = 6.8 Hz, 1H), 3.63 (dd, J = 6.8 and 16.4 Hz, 2H), 3.42 (dd, J = 6.8 and 16.4 Hz, 2H); ¹³C NMR (100 MHz, CDCl₃, δ, p.p.m.): 198.56, 162.91, 149.10, 136.87, 136.37, 133.02, 128.51, 128.07, 124.12, 121.55, 43.54, 38.10; IR (KBr, ν, cm⁻¹): 3003, 2889, 1680, 1589, 1246, 1209, 997, 750, 688, 540. Elemental analysis, calculated for C₂₂H₁₉NO₂: C 80.22, H 5.81, N 4.25%; found: C 80.13, H 5.87, N 4.21%.

Computing details top

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

Figures top

	Fig. 1. A view of (I), with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A perspective view of the crystal packing of (I), along the c axis.

1,5-Diphenyl-3-(2-pyridyl)pentane-1,5-dione top

Crystal data top

C₂₂H₁₉NO₂	F(000) = 696
M_r = 329.38	D_x = 1.210 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.519 (2) Å	Cell parameters from 2451 reflections
b = 18.162 (3) Å	θ = 2.6–22.7°
c = 8.640 (3) Å	µ = 0.08 mm⁻¹
β = 90.213 (2)°	T = 298 K
V = 1807.5 (7) Å³	Block, colourless
Z = 4	0.55 × 0.52 × 0.47 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3189 independent reflections
Radiation source: fine-focus sealed tube	1889 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→8
T_min = 0.959, T_max = 0.965	k = −21→20
9346 measured reflections	l = −10→9

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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.0423P)² + 0.5691P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3189 reflections	Δρ_max = 0.16 e Å⁻³
227 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Bruker, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.049 (3)

Crystal data top

C₂₂H₁₉NO₂	V = 1807.5 (7) Å³
M_r = 329.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.519 (2) Å	µ = 0.08 mm⁻¹
b = 18.162 (3) Å	T = 298 K
c = 8.640 (3) Å	0.55 × 0.52 × 0.47 mm
β = 90.213 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3189 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1889 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.965	R_int = 0.052
9346 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.00	Δρ_max = 0.16 e Å⁻³
3189 reflections	Δρ_min = −0.16 e Å⁻³
227 parameters

Special details top

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	U_iso*/U_eq
N1	0.64986 (16)	0.06597 (10)	1.0878 (2)	0.0607 (5)
O1	0.71688 (14)	0.13498 (9)	0.73392 (19)	0.0693 (5)
O2	0.34654 (13)	0.21340 (9)	0.76615 (19)	0.0672 (5)
C1	0.7208 (2)	0.05815 (14)	1.2104 (3)	0.0749 (8)
H1	0.7534	0.0121	1.2282	0.090*
C2	0.7478 (2)	0.11372 (16)	1.3105 (3)	0.0714 (7)
H2	0.7969	0.1054	1.3944	0.086*
C3	0.7014 (2)	0.18165 (16)	1.2847 (3)	0.0704 (7)
H3	0.7189	0.2208	1.3501	0.085*
C4	0.6288 (2)	0.19114 (13)	1.1615 (3)	0.0611 (6)
H4	0.5961	0.2371	1.1420	0.073*
C5	0.60384 (17)	0.13239 (11)	1.0655 (2)	0.0446 (5)
C6	0.52172 (17)	0.14184 (11)	0.9310 (2)	0.0444 (5)
H6	0.5382	0.1895	0.8827	0.053*
C7	0.53681 (18)	0.08244 (11)	0.8084 (2)	0.0520 (6)
H7A	0.5207	0.0349	0.8547	0.062*
H7B	0.4801	0.0904	0.7268	0.062*
C8	0.65629 (19)	0.08037 (12)	0.7376 (2)	0.0504 (5)
C9	0.6982 (2)	0.01021 (13)	0.6683 (2)	0.0590 (6)
C10	0.6231 (3)	−0.04686 (14)	0.6304 (3)	0.0753 (8)
H10	0.5443	−0.0423	0.6509	0.090*
C11	0.6650 (4)	−0.11063 (16)	0.5621 (3)	0.1046 (12)
H11	0.6142	−0.1486	0.5366	0.125*
C12	0.7808 (5)	−0.1177 (2)	0.5325 (4)	0.1209 (16)
H12	0.8085	−0.1604	0.4861	0.145*
C13	0.8569 (4)	−0.0623 (2)	0.5706 (4)	0.1095 (12)
H13	0.9357	−0.0678	0.5510	0.131*
C14	0.8160 (3)	0.00239 (15)	0.6386 (3)	0.0812 (8)
H14	0.8674	0.0401	0.6638	0.097*
C15	0.39591 (17)	0.14319 (12)	0.9882 (2)	0.0508 (6)
H15A	0.3713	0.0931	1.0089	0.061*
H15B	0.3930	0.1702	1.0850	0.061*
C16	0.31204 (18)	0.17754 (11)	0.8762 (2)	0.0485 (5)
C17	0.18484 (18)	0.16906 (12)	0.9047 (2)	0.0511 (6)
C18	0.1408 (2)	0.12207 (15)	1.0154 (3)	0.0780 (8)
H18	0.1913	0.0944	1.0760	0.094*
C19	0.0221 (2)	0.1156 (2)	1.0373 (4)	0.1039 (11)
H19	−0.0064	0.0839	1.1127	0.125*
C20	−0.0520 (2)	0.1552 (2)	0.9497 (4)	0.1022 (11)
H20	−0.1316	0.1505	0.9640	0.123*
C21	−0.0103 (2)	0.20237 (19)	0.8394 (4)	0.0938 (10)
H21	−0.0617	0.2298	0.7794	0.113*
C22	0.1079 (2)	0.20944 (14)	0.8170 (3)	0.0697 (7)
H22	0.1356	0.2417	0.7421	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0584 (12)	0.0489 (11)	0.0748 (13)	−0.0032 (9)	−0.0136 (10)	0.0070 (10)
O1	0.0600 (10)	0.0636 (10)	0.0843 (12)	−0.0048 (9)	0.0146 (9)	−0.0002 (9)
O2	0.0561 (10)	0.0724 (11)	0.0731 (11)	0.0038 (8)	0.0021 (8)	0.0237 (9)
C1	0.0695 (17)	0.0632 (16)	0.092 (2)	−0.0010 (13)	−0.0235 (15)	0.0222 (15)
C2	0.0602 (16)	0.095 (2)	0.0592 (15)	−0.0094 (15)	−0.0136 (13)	0.0140 (15)
C3	0.0640 (17)	0.0848 (19)	0.0624 (15)	0.0010 (14)	−0.0129 (13)	−0.0150 (14)
C4	0.0612 (15)	0.0583 (14)	0.0636 (15)	0.0065 (11)	−0.0112 (12)	−0.0103 (12)
C5	0.0387 (11)	0.0469 (12)	0.0483 (12)	−0.0020 (9)	0.0015 (9)	0.0017 (10)
C6	0.0423 (12)	0.0438 (11)	0.0471 (12)	−0.0007 (9)	0.0001 (10)	0.0007 (9)
C7	0.0477 (13)	0.0547 (13)	0.0535 (13)	−0.0035 (10)	−0.0029 (10)	−0.0037 (10)
C8	0.0522 (14)	0.0548 (14)	0.0441 (12)	0.0058 (11)	−0.0010 (10)	0.0044 (10)
C9	0.0774 (18)	0.0577 (14)	0.0420 (13)	0.0191 (13)	0.0058 (12)	0.0085 (11)
C10	0.115 (2)	0.0593 (16)	0.0513 (15)	0.0120 (16)	0.0015 (14)	−0.0021 (12)
C11	0.184 (4)	0.0654 (19)	0.0644 (19)	0.026 (2)	−0.002 (2)	−0.0078 (15)
C12	0.204 (5)	0.087 (3)	0.072 (2)	0.069 (3)	0.020 (3)	0.0042 (19)
C13	0.130 (3)	0.114 (3)	0.085 (2)	0.066 (3)	0.033 (2)	0.018 (2)
C14	0.091 (2)	0.0858 (19)	0.0671 (17)	0.0346 (16)	0.0179 (15)	0.0160 (14)
C15	0.0449 (12)	0.0568 (13)	0.0507 (13)	0.0007 (10)	0.0001 (10)	0.0015 (10)
C16	0.0478 (13)	0.0451 (12)	0.0525 (13)	0.0022 (10)	0.0011 (10)	−0.0017 (10)
C17	0.0445 (13)	0.0595 (13)	0.0492 (13)	0.0043 (10)	−0.0027 (10)	−0.0051 (11)
C18	0.0470 (15)	0.109 (2)	0.0781 (18)	−0.0021 (14)	−0.0036 (13)	0.0255 (16)
C19	0.0511 (17)	0.161 (3)	0.100 (2)	−0.0144 (18)	0.0012 (16)	0.036 (2)
C20	0.0430 (16)	0.169 (3)	0.095 (2)	−0.0013 (19)	−0.0018 (17)	0.007 (2)
C21	0.0516 (18)	0.136 (3)	0.093 (2)	0.0231 (17)	−0.0114 (16)	0.007 (2)
C22	0.0552 (16)	0.0854 (18)	0.0685 (16)	0.0133 (13)	−0.0028 (13)	0.0062 (14)

Geometric parameters (Å, º) top

N1—C5	1.331 (3)	C10—H10	0.9300
N1—C1	1.343 (3)	C11—C12	1.366 (5)
O1—C8	1.213 (2)	C11—H11	0.9300
O2—C16	1.220 (2)	C12—C13	1.374 (5)
C1—C2	1.364 (3)	C12—H12	0.9300
C1—H1	0.9300	C13—C14	1.396 (4)
C2—C3	1.363 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.362 (3)	C15—C16	1.501 (3)
C3—H3	0.9300	C15—H15A	0.9700
C4—C5	1.381 (3)	C15—H15B	0.9700
C4—H4	0.9300	C16—C17	1.495 (3)
C5—C6	1.506 (3)	C17—C22	1.376 (3)
C6—C7	1.522 (3)	C17—C18	1.380 (3)
C6—C15	1.533 (3)	C18—C19	1.385 (3)
C6—H6	0.9800	C18—H18	0.9300
C7—C8	1.509 (3)	C19—C20	1.347 (4)
C7—H7A	0.9700	C19—H19	0.9300
C7—H7B	0.9700	C20—C21	1.370 (4)
C8—C9	1.489 (3)	C20—H20	0.9300
C9—C10	1.388 (3)	C21—C22	1.381 (4)
C9—C14	1.390 (3)	C21—H21	0.9300
C10—C11	1.387 (4)	C22—H22	0.9300

C5—N1—C1	116.8 (2)	C12—C11—H11	120.0
N1—C1—C2	123.9 (2)	C10—C11—H11	120.0
N1—C1—H1	118.0	C11—C12—C13	120.6 (3)
C2—C1—H1	118.0	C11—C12—H12	119.7
C3—C2—C1	118.6 (2)	C13—C12—H12	119.7
C3—C2—H2	120.7	C12—C13—C14	120.1 (4)
C1—C2—H2	120.7	C12—C13—H13	119.9
C4—C3—C2	118.8 (2)	C14—C13—H13	119.9
C4—C3—H3	120.6	C9—C14—C13	119.7 (3)
C2—C3—H3	120.6	C9—C14—H14	120.2
C3—C4—C5	119.8 (2)	C13—C14—H14	120.2
C3—C4—H4	120.1	C16—C15—C6	113.95 (17)
C5—C4—H4	120.1	C16—C15—H15A	108.8
N1—C5—C4	122.1 (2)	C6—C15—H15A	108.8
N1—C5—C6	117.61 (18)	C16—C15—H15B	108.8
C4—C5—C6	120.28 (19)	C6—C15—H15B	108.8
C5—C6—C7	112.54 (17)	H15A—C15—H15B	107.7
C5—C6—C15	110.17 (16)	O2—C16—C17	120.4 (2)
C7—C6—C15	110.25 (17)	O2—C16—C15	120.90 (19)
C5—C6—H6	107.9	C17—C16—C15	118.68 (18)
C7—C6—H6	107.9	C22—C17—C18	118.2 (2)
C15—C6—H6	107.9	C22—C17—C16	119.0 (2)
C8—C7—C6	113.99 (17)	C18—C17—C16	122.8 (2)
C8—C7—H7A	108.8	C17—C18—C19	120.9 (3)
C6—C7—H7A	108.8	C17—C18—H18	119.6
C8—C7—H7B	108.8	C19—C18—H18	119.6
C6—C7—H7B	108.8	C20—C19—C18	120.1 (3)
H7A—C7—H7B	107.6	C20—C19—H19	120.0
O1—C8—C9	120.1 (2)	C18—C19—H19	120.0
O1—C8—C7	121.05 (19)	C19—C20—C21	120.1 (3)
C9—C8—C7	118.8 (2)	C19—C20—H20	119.9
C10—C9—C14	119.2 (2)	C21—C20—H20	119.9
C10—C9—C8	122.1 (2)	C20—C21—C22	120.3 (3)
C14—C9—C8	118.7 (2)	C20—C21—H21	119.9
C11—C10—C9	120.5 (3)	C22—C21—H21	119.9
C11—C10—H10	119.8	C17—C22—C21	120.4 (3)
C9—C10—H10	119.8	C17—C22—H22	119.8
C12—C11—C10	120.0 (4)	C21—C22—H22	119.8

Experimental details

Crystal data
Chemical formula	C₂₂H₁₉NO₂
M_r	329.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.519 (2), 18.162 (3), 8.640 (3)
β (°)	90.213 (2)
V (Å³)	1807.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.55 × 0.52 × 0.47

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.959, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	9346, 3189, 1889
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.128, 1.00
No. of reflections	3189
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.16

Computer programs: SMART (Siemens, 1996), SMART, SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Selected geometric parameters (Å, º) top

O1—C8	1.213 (2)	C6—C7	1.522 (3)
O2—C16	1.220 (2)	C6—C15	1.533 (3)

C5—C6—C7	112.54 (17)	C7—C6—C15	110.25 (17)
C5—C6—C15	110.17 (16)

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