1-(4-Chloro­phen­yl)-3-(2-nitro­phenyl)propane-1,2-dione

Huang, L.; Li, S.; Li, H.

doi:10.1107/S1600536808030559

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o2024

doi:10.1107/S1600536808030559

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1-(4-Chlorophenyl)-3-(2-nitrophenyl)propane-1,2-dione

Lin Huang,^a ^* Shuqin Li ^a and Huisheng Li ^a

^aDepartment of Chemistry and Biology, Xiangfan University, Xiangfan 441053, People's Republic of China
^*Correspondence e-mail: xfhuanglin@163.com

(Received 10 September 2008; accepted 22 September 2008; online 27 September 2008)

The title compound, C₁₅H₁₀ClNO₄, belongs to the class of 1,2-diketones, which have important applications in both synthetic organic chemistry and supramolecular chemistry. A dihedral angle of 9.03 (1)° is found between the mean planes of the two benzene rings. C—H⋯O interactions help to stabilize the crystal structure.

Related literature

For the synthesis of the title compound, see: Barnes & Gist (1950 ). For applications of the title compound, see: Saalfrank et al. (1988 ); Schobert (1988 ); van Leusen & van Leusen (1977 ).

Experimental

Crystal data

C₁₅H₁₀ClNO₄
M_r = 303.69
Monoclinic, P 2₁ /c
a = 7.9995 (3) Å
b = 6.3730 (2) Å
c = 26.7750 (5) Å
β = 91.340 (2)°
V = 1364.64 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 298 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.943, T_max = 0.971
8762 measured reflections
2408 independent reflections
1872 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.133
S = 1.07
2408 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3ⁱ	0.93	2.53	3.279 (3)	138
C15—H15⋯O1	0.93	2.59	3.244 (3)	128
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030559/cs2095sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030559/cs2095Isup2.hkl

checkCIF report

Comment top

1,2-Diketones are important intermediates in the preparation of heterocyclic compounds in synthetic chemistry (van Leusen & van Leusen, 1977; Saalfrank et al., 1988). In addition, they can also be used as ligands in supramolecular chemistry (Schobert, 1988). The molecular structure of the title compound is shown in Fig. 1. The dihedral angle of the two benzene rings is 9.03 (1)°. Molecules are mainly connected by an intermolecular C—H···O interaction.

Related literature top

For the synthesis of the title compound, see: Barnes & Gist (1950). For applications of the title compound, see: Saalfrank et al. (1988); Schobert (1988); van Leusen & van Leusen (1977).

Experimental top

The title compound was synthesized as previously described by Barnes & Gist (1950). Colorless crystals suitable for X-ray data collection were obtained by slow evaporation of a 5:2 ratio CH₂Cl₂:MeOH solution at 293 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the title molecule showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by spheres of arbitrary radius.

1-(4-Chlorophenyl)-3-(2-nitrophenyl)propane-1,2-dione top

Crystal data top

C₁₅H₁₀ClNO₄	F(000) = 624
M_r = 303.69	D_x = 1.478 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2433 reflections
a = 7.9995 (3) Å	θ = 2.6–23.4°
b = 6.3730 (2) Å	µ = 0.30 mm⁻¹
c = 26.7750 (5) Å	T = 298 K
β = 91.340 (2)°	Block, colourless
V = 1364.64 (7) Å³	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2408 independent reflections
Radiation source: fine-focus sealed tube	1872 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −9→9
T_min = 0.943, T_max = 0.971	k = −7→7
8762 measured reflections	l = −31→31

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0688P)² + 0.2924P] where P = (F_o² + 2F_c²)/3
2408 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₅H₁₀ClNO₄	V = 1364.64 (7) Å³
M_r = 303.69	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9995 (3) Å	µ = 0.30 mm⁻¹
b = 6.3730 (2) Å	T = 298 K
c = 26.7750 (5) Å	0.20 × 0.10 × 0.10 mm
β = 91.340 (2)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2408 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	1872 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.971	R_int = 0.027
8762 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.07	Δρ_max = 0.38 e Å⁻³
2408 reflections	Δρ_min = −0.28 e Å⁻³
190 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.4590 (2)	0.5187 (3)	0.67527 (7)	0.0496 (5)
C2	0.4028 (3)	0.7133 (3)	0.65828 (7)	0.0498 (5)
C3	0.2727 (3)	0.8197 (4)	0.68005 (9)	0.0606 (6)
H3	0.2382	0.9492	0.6676	0.073*
C4	0.1952 (3)	0.7326 (5)	0.72019 (9)	0.0675 (7)
H4	0.1075	0.8028	0.7351	0.081*
C5	0.2471 (3)	0.5421 (4)	0.73831 (9)	0.0669 (7)
H5	0.1947	0.4829	0.7656	0.080*
C6	0.3771 (3)	0.4379 (4)	0.71616 (8)	0.0588 (6)
H6	0.4111	0.3089	0.7291	0.071*
C7	0.6000 (3)	0.3935 (4)	0.65391 (9)	0.0602 (6)
H7A	0.6018	0.2561	0.6695	0.072*
H7B	0.5777	0.3735	0.6185	0.072*
C8	0.7691 (3)	0.4913 (3)	0.66072 (7)	0.0504 (5)
C9	0.9136 (3)	0.3769 (4)	0.63586 (8)	0.0539 (5)
C10	1.0144 (2)	0.4879 (3)	0.59876 (7)	0.0471 (5)
C11	1.1423 (3)	0.3809 (4)	0.57538 (8)	0.0568 (6)
H11	1.1665	0.2433	0.5846	0.068*
C12	1.2338 (3)	0.4757 (4)	0.53865 (8)	0.0631 (6)
H12	1.3183	0.4029	0.5228	0.076*
C13	1.1976 (3)	0.6808 (4)	0.52582 (8)	0.0571 (6)
C14	1.0729 (3)	0.7893 (4)	0.54892 (8)	0.0572 (6)
H14	1.0505	0.9278	0.5401	0.069*
C15	0.9814 (3)	0.6933 (3)	0.58507 (8)	0.0536 (5)
H15	0.8965	0.7669	0.6005	0.064*
Cl1	1.31213 (9)	0.80635 (13)	0.48046 (2)	0.0813 (3)
N1	0.4783 (3)	0.8163 (4)	0.61492 (7)	0.0653 (6)
O1	0.5769 (2)	0.7162 (4)	0.58971 (7)	0.0969 (7)
O2	0.4318 (3)	0.9934 (3)	0.60410 (8)	0.0994 (7)
O3	0.79710 (19)	0.6406 (3)	0.68656 (6)	0.0693 (5)
O4	0.9394 (2)	0.1971 (3)	0.64872 (8)	0.0855 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0428 (11)	0.0539 (13)	0.0520 (11)	−0.0072 (9)	−0.0024 (9)	−0.0057 (10)
C2	0.0441 (11)	0.0588 (14)	0.0463 (11)	−0.0084 (10)	−0.0063 (9)	−0.0001 (10)
C3	0.0509 (13)	0.0614 (15)	0.0687 (15)	0.0020 (11)	−0.0109 (11)	−0.0052 (11)
C4	0.0447 (13)	0.0881 (19)	0.0697 (15)	0.0040 (12)	0.0022 (11)	−0.0143 (14)
C5	0.0516 (14)	0.0881 (19)	0.0614 (14)	−0.0112 (13)	0.0082 (11)	0.0013 (13)
C6	0.0538 (13)	0.0602 (14)	0.0623 (13)	−0.0091 (11)	−0.0032 (10)	0.0065 (11)
C7	0.0574 (14)	0.0606 (14)	0.0627 (13)	−0.0031 (11)	0.0040 (10)	−0.0117 (11)
C8	0.0533 (13)	0.0521 (13)	0.0461 (11)	0.0014 (10)	0.0050 (9)	0.0032 (10)
C9	0.0544 (13)	0.0497 (13)	0.0579 (12)	0.0040 (10)	0.0038 (10)	0.0016 (10)
C10	0.0448 (11)	0.0478 (12)	0.0485 (11)	0.0002 (9)	−0.0008 (9)	−0.0050 (9)
C11	0.0542 (13)	0.0491 (13)	0.0676 (14)	0.0044 (10)	0.0066 (10)	−0.0056 (10)
C12	0.0537 (14)	0.0705 (17)	0.0655 (14)	0.0015 (12)	0.0141 (11)	−0.0154 (12)
C13	0.0509 (13)	0.0724 (17)	0.0479 (12)	−0.0099 (11)	0.0004 (10)	−0.0030 (10)
C14	0.0580 (13)	0.0548 (13)	0.0589 (13)	−0.0014 (11)	0.0016 (10)	0.0049 (10)
C15	0.0492 (12)	0.0549 (14)	0.0568 (12)	0.0055 (10)	0.0047 (9)	0.0001 (10)
Cl1	0.0776 (5)	0.1050 (6)	0.0619 (4)	−0.0200 (4)	0.0179 (3)	0.0070 (3)
N1	0.0593 (12)	0.0772 (16)	0.0588 (12)	−0.0135 (11)	−0.0082 (10)	0.0125 (11)
O1	0.0753 (13)	0.143 (2)	0.0732 (13)	0.0231 (13)	0.0198 (10)	0.0355 (12)
O2	0.140 (2)	0.0620 (13)	0.0966 (14)	−0.0183 (13)	0.0092 (13)	0.0166 (11)
O3	0.0546 (9)	0.0763 (11)	0.0774 (11)	−0.0077 (8)	0.0083 (8)	−0.0257 (9)
O4	0.0905 (14)	0.0608 (12)	0.1068 (14)	0.0187 (10)	0.0394 (11)	0.0232 (10)

Geometric parameters (Å, º) top

C1—C6	1.388 (3)	C8—C9	1.532 (3)
C1—C2	1.392 (3)	C9—O4	1.213 (3)
C1—C7	1.505 (3)	C9—C10	1.475 (3)
C2—C3	1.382 (3)	C10—C15	1.383 (3)
C2—N1	1.475 (3)	C10—C11	1.390 (3)
C3—C4	1.371 (3)	C11—C12	1.379 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.368 (4)	C12—C13	1.380 (3)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.380 (3)	C13—C14	1.373 (3)
C5—H5	0.9300	C13—Cl1	1.734 (2)
C6—H6	0.9300	C14—C15	1.371 (3)
C7—C8	1.497 (3)	C14—H14	0.9300
C7—H7A	0.9700	C15—H15	0.9300
C7—H7B	0.9700	N1—O2	1.221 (3)
C8—O3	1.195 (3)	N1—O1	1.229 (3)

C6—C1—C2	115.7 (2)	C7—C8—C9	115.99 (19)
C6—C1—C7	118.3 (2)	O4—C9—C10	123.5 (2)
C2—C1—C7	126.0 (2)	O4—C9—C8	116.8 (2)
C3—C2—C1	122.7 (2)	C10—C9—C8	119.63 (19)
C3—C2—N1	116.1 (2)	C15—C10—C11	118.9 (2)
C1—C2—N1	121.2 (2)	C15—C10—C9	121.91 (19)
C4—C3—C2	119.4 (2)	C11—C10—C9	119.2 (2)
C4—C3—H3	120.3	C12—C11—C10	120.9 (2)
C2—C3—H3	120.3	C12—C11—H11	119.5
C5—C4—C3	119.9 (2)	C10—C11—H11	119.5
C5—C4—H4	120.1	C11—C12—C13	118.7 (2)
C3—C4—H4	120.1	C11—C12—H12	120.6
C4—C5—C6	120.0 (2)	C13—C12—H12	120.6
C4—C5—H5	120.0	C14—C13—C12	121.0 (2)
C6—C5—H5	120.0	C14—C13—Cl1	119.0 (2)
C5—C6—C1	122.3 (2)	C12—C13—Cl1	119.99 (18)
C5—C6—H6	118.8	C15—C14—C13	119.9 (2)
C1—C6—H6	118.8	C15—C14—H14	120.0
C8—C7—C1	114.60 (19)	C13—C14—H14	120.0
C8—C7—H7A	108.6	C14—C15—C10	120.5 (2)
C1—C7—H7A	108.6	C14—C15—H15	119.7
C8—C7—H7B	108.6	C10—C15—H15	119.7
C1—C7—H7B	108.6	O2—N1—O1	123.0 (2)
H7A—C7—H7B	107.6	O2—N1—C2	118.0 (2)
O3—C8—C7	123.96 (19)	O1—N1—C2	118.8 (2)
O3—C8—C9	119.84 (19)

C6—C1—C2—C3	−0.7 (3)	O4—C9—C10—C15	−179.9 (2)
C7—C1—C2—C3	−179.6 (2)	C8—C9—C10—C15	−0.7 (3)
C6—C1—C2—N1	−179.61 (18)	O4—C9—C10—C11	2.6 (3)
C7—C1—C2—N1	1.4 (3)	C8—C9—C10—C11	−178.20 (19)
C1—C2—C3—C4	0.3 (3)	C15—C10—C11—C12	−0.9 (3)
N1—C2—C3—C4	179.30 (19)	C9—C10—C11—C12	176.7 (2)
C2—C3—C4—C5	0.1 (3)	C10—C11—C12—C13	0.8 (3)
C3—C4—C5—C6	−0.1 (4)	C11—C12—C13—C14	−0.1 (3)
C4—C5—C6—C1	−0.3 (4)	C11—C12—C13—Cl1	179.04 (17)
C2—C1—C6—C5	0.7 (3)	C12—C13—C14—C15	−0.5 (3)
C7—C1—C6—C5	179.7 (2)	Cl1—C13—C14—C15	−179.67 (17)
C6—C1—C7—C8	−112.2 (2)	C13—C14—C15—C10	0.4 (3)
C2—C1—C7—C8	66.7 (3)	C11—C10—C15—C14	0.2 (3)
C1—C7—C8—O3	9.9 (3)	C9—C10—C15—C14	−177.2 (2)
C1—C7—C8—C9	−175.36 (19)	C3—C2—N1—O2	6.2 (3)
O3—C8—C9—O4	115.7 (3)	C1—C2—N1—O2	−174.8 (2)
C7—C8—C9—O4	−59.3 (3)	C3—C2—N1—O1	−169.5 (2)
O3—C8—C9—C10	−63.5 (3)	C1—C2—N1—O1	9.5 (3)
C7—C8—C9—C10	121.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.93	2.53	3.279 (3)	138
C15—H15···O1	0.93	2.59	3.244 (3)	128

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀ClNO₄
M_r	303.69
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.9995 (3), 6.3730 (2), 26.7750 (5)
β (°)	91.340 (2)
V (Å³)	1364.64 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.943, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	8762, 2408, 1872
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.133, 1.07
No. of reflections	2408
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.28

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

C2—N1	1.475 (3)	C13—Cl1	1.734 (2)
C8—O3	1.195 (3)	N1—O2	1.221 (3)
C8—C9	1.532 (3)	N1—O1	1.229 (3)
C9—O4	1.213 (3)

C3—C2—N1	116.1 (2)	C7—C8—C9	115.99 (19)
C1—C2—N1	121.2 (2)	O4—C9—C10	123.5 (2)
C8—C7—C1	114.60 (19)	O4—C9—C8	116.8 (2)
O3—C8—C7	123.96 (19)	C10—C9—C8	119.63 (19)
O3—C8—C9	119.84 (19)	O2—N1—O1	123.0 (2)

C1—C7—C8—O3	9.9 (3)	O3—C8—C9—C10	−63.5 (3)
C1—C7—C8—C9	−175.36 (19)	C7—C8—C9—C10	121.5 (2)
O3—C8—C9—O4	115.7 (3)	O4—C9—C10—C15	−179.9 (2)
C7—C8—C9—O4	−59.3 (3)	O4—C9—C10—C11	2.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.93	2.53	3.279 (3)	138
C15—H15···O1	0.93	2.59	3.244 (3)	128

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

Acknowledgements

The authors are grateful to Xiangfan University for financial support.

References

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