Literature DB >> 21582177

1,5-Bis(4-chloro-phen-yl)-3-[4-(dimethyl-amino)phen-yl]pentane-1,5-dione.

Abstract

In the title mol-ecule, C(25)H(23)Cl(2)NO(2), the central benzene ring forms dihedral angles of 81.88 (7) and 89.22 (7)° with the two 4-chloro-phenyl fragments. The crystal packing exhibits weak inter-molecular C-H⋯O hydrogen bonds and π-π inter-actions [centroid-centroid distance 3.724 (3) Å].

Entities: CellLine Chemical Disease Gene

Year: 2009 PMID： 21582177 PMCID： PMC2968596 DOI： 10.1107/S1600536809003894

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the crystal structures of related compounds, see: Das et al. (1994 ▶); Huang et al. (2006 ▶).

Experimental

Crystal data

C25H23Cl2NO2 M = 440.34 Triclinic, a = 6.1059 (11) Å b = 12.5660 (16) Å c = 14.731 (2) Å α = 75.516 (1)° β = 85.953 (2)° γ = 87.215 (2)° V = 1091.1 (3) Å3 Z = 2 Mo Kα radiation μ = 0.32 mm−1 T = 298 (2) K 0.49 × 0.44 × 0.41 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.859, T max = 0.880 5699 measured reflections 3783 independent reflections 1846 reflections with I > 2σ(I) R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.141 S = 0.99 3783 reflections 273 parameters H-atom parameters constrained Δρmax = 0.18 e Å−3 Δρmin = −0.28 e Å−3 Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003894/cv2508sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003894/cv2508Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₅H₂₃Cl₂NO₂	Z = 2
M_r = 440.34	F(000) = 460
Triclinic, P1	D_x = 1.340 Mg m⁻³
a = 6.1059 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.5660 (16) Å	Cell parameters from 1234 reflections
c = 14.731 (2) Å	θ = 2.5–22.3°
α = 75.516 (1)°	µ = 0.32 mm⁻¹
β = 85.953 (2)°	T = 298 K
γ = 87.215 (2)°	Block, colourless
V = 1091.1 (3) Å³	0.49 × 0.44 × 0.41 mm

Bruker SMART APEX CCD area-detector diffractometer	3783 independent reflections
Radiation source: fine-focus sealed tube	1846 reflections with I > 2σ(I)
graphite	R_int = 0.024
φ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.859, T_max = 0.880	k = −8→14
5699 measured reflections	l = −17→17

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0595P)²] where P = (F_o² + 2F_c²)/3
3783 reflections	(Δ/σ)_max = 0.001
273 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
Cl1	1.1281 (2)	0.35929 (8)	0.70584 (7)	0.1057 (4)
Cl2	0.8066 (2)	1.57712 (9)	0.06677 (8)	0.1334 (5)
N1	0.5447 (5)	0.8356 (3)	0.0253 (2)	0.0836 (9)
O1	0.4561 (4)	0.75133 (19)	0.48581 (16)	0.0838 (8)
O2	0.3440 (4)	1.12960 (19)	0.32504 (17)	0.0811 (7)
C1	0.6537 (6)	0.7566 (3)	0.4892 (2)	0.0550 (8)
C2	0.7662 (5)	0.8611 (2)	0.4432 (2)	0.0560 (8)
H2A	0.8980	0.8441	0.4080	0.067*
H2B	0.8109	0.8943	0.4914	0.067*
C3	0.6236 (5)	0.9442 (2)	0.3771 (2)	0.0551 (8)
H3	0.4755	0.9419	0.4076	0.066*
C4	0.7007 (5)	1.0611 (2)	0.3626 (2)	0.0587 (9)
H4A	0.7239	1.0744	0.4232	0.070*
H4B	0.8403	1.0685	0.3262	0.070*
C5	0.5388 (6)	1.1462 (3)	0.3128 (2)	0.0556 (8)
C6	0.7791 (5)	0.6593 (2)	0.54189 (19)	0.0486 (8)
C7	0.9857 (5)	0.6658 (3)	0.5707 (2)	0.0573 (8)
H7	1.0549	0.7328	0.5548	0.069*
C8	1.0912 (6)	0.5741 (3)	0.6229 (2)	0.0667 (9)
H8	1.2297	0.5793	0.6437	0.080*
C9	0.9908 (7)	0.4750 (3)	0.6441 (2)	0.0650 (9)
C10	0.7867 (7)	0.4664 (3)	0.6155 (2)	0.0744 (10)
H10	0.7202	0.3987	0.6294	0.089*
C11	0.6806 (6)	0.5591 (3)	0.5657 (2)	0.0635 (9)
H11	0.5392	0.5541	0.5476	0.076*
C12	0.6156 (6)	1.2513 (3)	0.2519 (2)	0.0546 (8)
C13	0.8291 (6)	1.2674 (3)	0.2151 (2)	0.0632 (9)
H13	0.9347	1.2109	0.2298	0.076*
C14	0.8859 (6)	1.3673 (3)	0.1565 (2)	0.0779 (11)
H14	1.0288	1.3779	0.1304	0.093*
C15	0.7308 (8)	1.4511 (3)	0.1368 (2)	0.0804 (11)
C16	0.5199 (8)	1.4378 (3)	0.1735 (2)	0.0854 (12)
H16	0.4164	1.4955	0.1604	0.102*
C17	0.4640 (6)	1.3385 (3)	0.2298 (2)	0.0707 (10)
H17	0.3198	1.3286	0.2544	0.085*
C18	0.6048 (5)	0.9143 (2)	0.2842 (2)	0.0490 (8)
C19	0.7708 (5)	0.9307 (2)	0.2150 (2)	0.0572 (8)
H19	0.9003	0.9603	0.2258	0.069*
C20	0.7540 (6)	0.9053 (3)	0.1304 (2)	0.0632 (9)
H20	0.8705	0.9189	0.0853	0.076*
C21	0.5653 (6)	0.8595 (3)	0.1113 (2)	0.0596 (9)
C22	0.3988 (6)	0.8402 (3)	0.1817 (2)	0.0663 (9)
H22	0.2711	0.8079	0.1723	0.080*
C23	0.4195 (5)	0.8681 (2)	0.2655 (2)	0.0597 (9)
H23	0.3035	0.8551	0.3109	0.072*
C24	0.7091 (7)	0.8654 (3)	−0.0499 (3)	0.0939 (13)
H24A	0.7429	0.9413	−0.0588	0.141*
H24B	0.6554	0.8546	−0.1066	0.141*
H24C	0.8393	0.8202	−0.0348	0.141*
C25	0.3520 (7)	0.7852 (4)	0.0080 (3)	0.1137 (16)
H25A	0.3125	0.7267	0.0617	0.171*
H25B	0.3806	0.7559	−0.0461	0.171*
H25C	0.2334	0.8390	−0.0031	0.171*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1403 (11)	0.0722 (7)	0.0954 (8)	0.0259 (6)	−0.0218 (7)	−0.0052 (6)
Cl2	0.1990 (14)	0.0788 (8)	0.0976 (9)	0.0017 (8)	0.0142 (9)	0.0169 (6)
N1	0.092 (3)	0.096 (2)	0.072 (2)	0.0026 (19)	−0.0208 (19)	−0.0359 (19)
O1	0.0554 (16)	0.0829 (18)	0.0964 (19)	−0.0125 (13)	−0.0049 (14)	0.0110 (14)
O2	0.0617 (17)	0.0758 (18)	0.103 (2)	0.0036 (14)	−0.0004 (14)	−0.0203 (14)
C1	0.050 (2)	0.068 (2)	0.0468 (19)	−0.0123 (18)	0.0025 (16)	−0.0132 (17)
C2	0.059 (2)	0.060 (2)	0.0468 (18)	−0.0079 (17)	−0.0023 (16)	−0.0077 (16)
C3	0.054 (2)	0.057 (2)	0.052 (2)	−0.0022 (16)	−0.0017 (16)	−0.0100 (16)
C4	0.069 (2)	0.057 (2)	0.0517 (19)	0.0013 (18)	−0.0075 (17)	−0.0152 (16)
C5	0.059 (2)	0.060 (2)	0.053 (2)	0.0031 (19)	−0.0031 (18)	−0.0243 (18)
C6	0.051 (2)	0.053 (2)	0.0420 (18)	−0.0077 (17)	0.0049 (15)	−0.0128 (15)
C7	0.053 (2)	0.057 (2)	0.061 (2)	−0.0062 (17)	−0.0018 (17)	−0.0117 (17)
C8	0.063 (2)	0.069 (3)	0.067 (2)	−0.001 (2)	−0.0065 (18)	−0.015 (2)
C9	0.088 (3)	0.054 (2)	0.052 (2)	0.007 (2)	−0.0023 (19)	−0.0143 (18)
C10	0.095 (3)	0.054 (2)	0.076 (3)	−0.017 (2)	−0.004 (2)	−0.017 (2)
C11	0.066 (2)	0.058 (2)	0.069 (2)	−0.0129 (19)	−0.0041 (19)	−0.0183 (19)
C12	0.067 (2)	0.055 (2)	0.0439 (19)	0.0068 (18)	−0.0083 (17)	−0.0152 (16)
C13	0.070 (3)	0.063 (2)	0.053 (2)	0.0080 (19)	−0.0059 (18)	−0.0078 (18)
C14	0.083 (3)	0.083 (3)	0.061 (2)	−0.002 (2)	−0.002 (2)	−0.005 (2)
C15	0.112 (4)	0.064 (3)	0.054 (2)	0.009 (2)	−0.002 (2)	0.0012 (19)
C16	0.110 (4)	0.074 (3)	0.061 (2)	0.027 (2)	−0.007 (2)	−0.002 (2)
C17	0.079 (3)	0.075 (3)	0.054 (2)	0.014 (2)	−0.0021 (19)	−0.012 (2)
C18	0.048 (2)	0.0485 (19)	0.0488 (19)	0.0037 (15)	−0.0034 (16)	−0.0098 (15)
C19	0.052 (2)	0.061 (2)	0.061 (2)	−0.0015 (16)	−0.0095 (17)	−0.0180 (17)
C20	0.060 (2)	0.069 (2)	0.059 (2)	0.0039 (18)	0.0010 (17)	−0.0168 (18)
C21	0.071 (2)	0.052 (2)	0.056 (2)	0.0113 (18)	−0.0178 (19)	−0.0124 (17)
C22	0.063 (2)	0.065 (2)	0.073 (3)	−0.0064 (18)	−0.018 (2)	−0.0177 (19)
C23	0.052 (2)	0.064 (2)	0.060 (2)	−0.0028 (17)	−0.0035 (17)	−0.0077 (18)
C24	0.114 (3)	0.109 (3)	0.063 (3)	0.018 (3)	−0.012 (2)	−0.032 (2)
C25	0.107 (4)	0.145 (4)	0.115 (4)	0.007 (3)	−0.039 (3)	−0.074 (3)

Cl1—C9	1.724 (3)	C11—H11	0.9300
Cl2—C15	1.724 (4)	C12—C13	1.380 (4)
N1—C21	1.389 (4)	C12—C17	1.389 (4)
N1—C24	1.430 (4)	C13—C14	1.378 (5)
N1—C25	1.431 (4)	C13—H13	0.9300
O1—C1	1.217 (3)	C14—C15	1.371 (5)
O2—C5	1.211 (3)	C14—H14	0.9300
C1—C6	1.484 (4)	C15—C16	1.362 (5)
C1—C2	1.495 (4)	C16—C17	1.359 (5)
C2—C3	1.523 (4)	C16—H16	0.9300
C2—H2A	0.9700	C17—H17	0.9300
C2—H2B	0.9700	C18—C19	1.371 (4)
C3—C18	1.519 (4)	C18—C23	1.372 (4)
C3—C4	1.523 (4)	C19—C20	1.373 (4)
C3—H3	0.9800	C19—H19	0.9300
C4—C5	1.505 (4)	C20—C21	1.389 (4)
C4—H4A	0.9700	C20—H20	0.9300
C4—H4B	0.9700	C21—C22	1.384 (4)
C5—C12	1.476 (4)	C22—C23	1.381 (4)
C6—C7	1.371 (4)	C22—H22	0.9300
C6—C11	1.376 (4)	C23—H23	0.9300
C7—C8	1.374 (4)	C24—H24A	0.9600
C7—H7	0.9300	C24—H24B	0.9600
C8—C9	1.370 (4)	C24—H24C	0.9600
C8—H8	0.9300	C25—H25A	0.9600
C9—C10	1.361 (4)	C25—H25B	0.9600
C10—C11	1.371 (5)	C25—H25C	0.9600
C10—H10	0.9300

Cg···Cgⁱ	3.724 (3)

C21—N1—C24	121.3 (3)	C17—C12—C5	118.1 (3)
C21—N1—C25	120.5 (3)	C14—C13—C12	120.0 (3)
C24—N1—C25	118.1 (3)	C14—C13—H13	120.0
O1—C1—C6	119.2 (3)	C12—C13—H13	120.0
O1—C1—C2	120.1 (3)	C15—C14—C13	119.7 (4)
C6—C1—C2	120.8 (3)	C15—C14—H14	120.1
C1—C2—C3	113.6 (3)	C13—C14—H14	120.1
C1—C2—H2A	108.9	C16—C15—C14	121.4 (4)
C3—C2—H2A	108.9	C16—C15—Cl2	119.4 (3)
C1—C2—H2B	108.9	C14—C15—Cl2	119.2 (4)
C3—C2—H2B	108.9	C17—C16—C15	118.6 (4)
H2A—C2—H2B	107.7	C17—C16—H16	120.7
C18—C3—C4	111.8 (2)	C15—C16—H16	120.7
C18—C3—C2	112.2 (2)	C16—C17—C12	122.0 (4)
C4—C3—C2	111.8 (2)	C16—C17—H17	119.0
C18—C3—H3	106.9	C12—C17—H17	119.0
C4—C3—H3	106.9	C19—C18—C23	116.2 (3)
C2—C3—H3	106.9	C19—C18—C3	122.4 (3)
C5—C4—C3	112.6 (3)	C23—C18—C3	121.4 (3)
C5—C4—H4A	109.1	C18—C19—C20	122.8 (3)
C3—C4—H4A	109.1	C18—C19—H19	118.6
C5—C4—H4B	109.1	C20—C19—H19	118.6
C3—C4—H4B	109.1	C19—C20—C21	120.9 (3)
H4A—C4—H4B	107.8	C19—C20—H20	119.6
O2—C5—C12	119.8 (3)	C21—C20—H20	119.6
O2—C5—C4	119.8 (3)	C22—C21—C20	116.8 (3)
C12—C5—C4	120.4 (3)	C22—C21—N1	121.9 (3)
C7—C6—C11	118.7 (3)	C20—C21—N1	121.3 (3)
C7—C6—C1	122.8 (3)	C23—C22—C21	121.0 (3)
C11—C6—C1	118.5 (3)	C23—C22—H22	119.5
C6—C7—C8	120.5 (3)	C21—C22—H22	119.5
C6—C7—H7	119.7	C18—C23—C22	122.4 (3)
C8—C7—H7	119.7	C18—C23—H23	118.8
C9—C8—C7	119.5 (3)	C22—C23—H23	118.8
C9—C8—H8	120.2	N1—C24—H24A	109.5
C7—C8—H8	120.2	N1—C24—H24B	109.5
C10—C9—C8	120.9 (3)	H24A—C24—H24B	109.5
C10—C9—Cl1	119.7 (3)	N1—C24—H24C	109.5
C8—C9—Cl1	119.3 (3)	H24A—C24—H24C	109.5
C9—C10—C11	119.0 (3)	H24B—C24—H24C	109.5
C9—C10—H10	120.5	N1—C25—H25A	109.5
C11—C10—H10	120.5	N1—C25—H25B	109.5
C10—C11—C6	121.3 (3)	H25A—C25—H25B	109.5
C10—C11—H11	119.4	N1—C25—H25C	109.5
C6—C11—H11	119.4	H25A—C25—H25C	109.5
C13—C12—C17	118.3 (3)	H25B—C25—H25C	109.5
C13—C12—C5	123.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1ⁱⁱ	0.93	2.58	3.176 (4)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1ⁱ	0.93	2.58	3.176 (4)	122

Symmetry code: (i) .

1 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

1 in total

1. 1,5-Bis(4-chloro-phen-yl)-3-(4-methyl-phen-yl)pentane-1,5-dione.

Authors: R Chithiravel; A Thiruvalluvar; S Muthusubramanian; R J Butcher
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2013-09-07

1 in total