Home Crystal structure of 2-bromo-7-(4-(dimethylamino)phenyl)-10-methylacridin-9 (10H)-one, C22H19BrN2O
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Crystal structure of 2-bromo-7-(4-(dimethylamino)phenyl)-10-methylacridin-9 (10H)-one, C22H19BrN2O

  • Chen Songhua and Yang Jien EMAIL logo
Published/Copyright: October 18, 2018

Abstract

C22H19BrN2O, monoclinic, P21/n (no. 14), a = 8.0338(16) Å, b = 9.0803(18) Å, c = 24.281(5) Å, β = 95.78(3)°, V = 1762.28(60) Å3, Z = 4, Rgt(F) = 0.0871, wRref(F2) = 0.1595, T = 173(2) K.

CCDC no.: 1832466

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Yellow needle
Size:0.28 × 0.27 × 0.16 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:3.28 mm−1
Diffractometer, scan mode:Raxis Rapid IP, ω-scans
θmax, completeness:68.2°, >99%
N(hkl)measured, N(hkl)unique, Rint:10538, 3191, 0.072
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2473
N(param)refined:238
Programs:Rigaku programs [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
Br11.23583(11)0.90232(9)0.45257(3)0.0455(3)
O10.7414(6)0.7378(5)0.57442(19)0.0400(13)
N11.0834(6)0.4050(6)0.6071(2)0.0263(12)
N20.1123(7)0.4600(6)0.8303(2)0.0289(13)
C11.1854(9)0.7441(8)0.4991(3)0.0309(16)
C21.3011(9)0.6334(8)0.5112(3)0.0393(19)
H21.4036130.6346690.4947680.047*
C31.2694(9)0.5212(8)0.5468(3)0.0383(18)
H31.3505090.4460890.5548880.046*
C41.1172(8)0.5167(7)0.5713(2)0.0240(14)
C51.0035(8)0.6337(7)0.5594(2)0.0226(14)
C61.0382(8)0.7449(7)0.5229(2)0.0260(15)
H60.9593890.8216890.5145270.031*
C70.8461(8)0.6418(7)0.5857(3)0.0242(14)
C80.8286(8)0.5293(6)0.6287(2)0.0195(13)
C90.9469(7)0.4158(7)0.6377(2)0.0215(13)
C101.1916(9)0.2771(8)0.6129(3)0.0371(18)
H10A1.2412030.2600600.5782340.056*
H10B1.1260910.1906180.6216610.056*
H10C1.2807150.2939820.6429060.056*
C110.9252(8)0.3134(7)0.6805(2)0.0252(15)
H111.0022370.2347620.6878450.030*
C120.7915(8)0.3287(7)0.7115(3)0.0255(15)
H120.7805070.2602400.7404450.031*
C130.6706(7)0.4403(6)0.7024(2)0.0195(13)
C140.6948(7)0.5401(7)0.6606(2)0.0192(13)
H140.6171650.6183940.6535300.023*
C150.5289(7)0.4515(6)0.7366(2)0.0182(13)
C160.3813(7)0.5261(7)0.7184(2)0.0223(14)
H160.3733900.5740370.6834170.027*
C170.2474(8)0.5324(7)0.7492(3)0.0260(14)
H170.1505040.5856590.7352890.031*
C180.2496(8)0.4630(7)0.8004(2)0.0219(14)
C190.3999(8)0.3930(7)0.8201(3)0.0270(15)
H190.4092550.3487620.8557660.032*
C200.5339(8)0.3872(7)0.7890(2)0.0236(14)
H200.6329440.3378790.8036130.028*
C210.1252(9)0.3969(8)0.8852(3)0.0350(17)
H21A0.1770470.2993270.8845440.053*
H21B0.0132370.3877770.8975830.053*
H21C0.1940740.4609330.9108050.053*
C22−0.0270(8)0.5581(8)0.8158(3)0.0336(17)
H22B0.0085470.6600760.8231940.050*
H22C−0.1186090.5338110.8379900.050*
H22A−0.0654240.5470330.7764140.050*

Source of materials

The title compound was obtained by Suzuki coupling reaction of 2,7-dibromo-10-methylacridin-9(10H)-one and (4-(dimethylamino)phenyl)boronic acid with 1/1 ratio. The compound was purified through flash column chromatography. Single crystals were obtained by crystallization of the title compound from methanol.

Experimental details

The hydrogen atoms were placed with common isotropic displacement factors Uiso(H) = 1.2 times Ueq(C, aromatic ring), and Uiso(H) = 1.5 times Ueq(C, methyl). The final refinement succeeded using geometrical restraints, with C—H = 0.95 Å (aromatic ring), and C—H = 0.98 Å (methyl).

Comment

The organic donor-acceptor (D-A) molecular materials with tuning optical nonlinear properties have attracted considerable academic and technological research attention [4], [5], [6], [7]. Acridone derivatives with electron-deficient properties are acceptor candidates in the constructing D-A molecules [8], [9]. N,N-dimethylaniline is the donor. The two parts are connected by a formal C–C single bond of 1.479(8) Å.

A view on the structure of the title molecule is shown in the figure. The asymmetric unit contains one molecule of the title compound. Bond lengths and angles are all in the expected ranges [11].

Acknowledgements

This work was supported by the research funds of Longyan University (LB2018016) and Doctoral Science foundation of Henan Normal University (No. 01026500259).

References

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Received: 2018-08-17
Accepted: 2018-10-07
Published Online: 2018-10-18
Published in Print: 2018-12-19

©2018 Chen Songhua et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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