10-[2-(Dimethyl­amino)eth­yl]-9-(4-methoxy­phen­yl)-3,3,6,6-tetra­methyl-3,4,6,7,9,10-hexa­hydro­acridine-1,8(2H,5H)-dione

Balamurugan, P.; Jagan, R.; Thiagarajan, V.; Yamin, B.M.; Sivakumar, K.

doi:10.1107/S1600536808043882

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o271

doi:10.1107/S1600536808043882

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10-[2-(Dimethylamino)ethyl]-9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione

P. Balamurugan,^a R. Jagan,^b V. Thiagarajan,^c Bohari M. Yamin ^d and K. Sivakumar ^b ^*

^aDepartment of Physics, Dhanalakshmi College of Engineering, Tambaram, Chennai 601 301, India, ^bDepartment of Physics, Anna University, Chennai 600 025, India, ^cNational Centre for Ultrafast Processes, University of Madras, Taramani Campus, Chennai 600 113, India, and ^dSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, UKM 43600, Bangi Selangor, Malaysia
^*Correspondence e-mail: ksivakumar@annauniv.edu

(Received 23 December 2008; accepted 24 December 2008; online 10 January 2009)

In the title compound, C₂₈H₃₈N₂O₃, the central ring of the acridinedione system adopts a boat conformation, while one of the outer rings adopts a half-chair conformation and the conformation of the other outer ring is between a sofa and a half-chair. The acridinedione system is buckled, with an angle of 22.01 (3)°. The crystal packing comprises layers of molecules laid parallel to the ac plane, being reinforced by an intermolecular C—H⋯O interaction.

Related literature

For related literature, see: Josephrajan et al. (2005 ); Murugan et al. (1998 ); Srividya et al. (1996 , 1998 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₈H₃₈N₂O₃
M_r = 450.60
Monoclinic, P 2₁ /n
a = 10.3030 (13) Å
b = 19.299 (3) Å
c = 13.3961 (18) Å
β = 103.336 (4)°
V = 2591.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 295 (2) K
0.56 × 0.16 × 0.10 mm

Data collection

Bruker KappaAPEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.95, T_max = 0.99
17538 measured reflections
5944 independent reflections
3567 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.162
S = 1.01
5944 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O1ⁱ	0.97	2.51	3.368 (2)	147
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808043882/tk2350sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043882/tk2350Isup2.hkl

checkCIF report

Comment top

Acridines, the earliest known antibiotics, are toxic towards bacteria. Some acridinedione derivatives show good inhibition against the pathogen Vibrio isolate-I (Josephrajan et al., 2005). Certain acridine-1,8-diones exhibit fluorescence activities (Murugan et al., 1998) and a few acridinedione derivatives also show photophysical (Srividya et al., 1998) and electrochemical properties (Srividya et al., 1996). Thus, the accurate description of crystal structures of substituted acridinediones are expected to provide useful information on the role of substituents in influencing molecular conformation which has a direct relationship to biological activity. This paper deals with the precise description of a 4-methoxyphenyl substituted tetramethyl acridinedione, (I).

The planar phenyl ring of the substituent moiety at C9 is perpendicular to the acridinedione moiety forming a dihedral angle of 88.21 (6)°, Fig. 1. The dimethylaminoethyl group is also oriented 80.0 (1)° to the acridinedione plane. The substitutuents at the C9 and N1 positions are cis oriented with respect to the acridinedione moiety and project opposite to the fold in the acridinedione moiety. The central ring of the acridinedione moiety adopts a boat conformation (ΔC_s (N1) = 0.028 (1)° & ΔC_s (C6—C1) = 0.057 (1)°). One of the outer rings (C1—C6) adopts a half-chair conformation (ΔC₂ (C1—C6) = 0.045 (1)°) and that of the other outer ring (C10—C15) ring is between a sofa and half chair conformation (ΔC_s (C10) = 0.066 (1)° & ΔC₂ (C10—C15) = 0.061 (1)°) (Nardelli, 1983). The crystal packing consists of layers of molecules laid parallel to the ac-plane. Only one of the two keto-O atoms participates in a C—H···O contact, Table 1.

Related literature top

For related literature, see: Josephrajan et al. (2005); Murugan et al. (1998); Srividya et al. (1996, 1998).

For related literature, see: Nardelli (1983).

Experimental top

Light-yellow crystals were obtained by recrystallization from an ethanol solution of (I).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity.

10-[2-(Dimethylamino)ethyl]-9-(4-methoxyphenyl)-3,3,6,6-tetramethyl- 3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione top

Crystal data top

C₂₈H₃₈N₂O₃	F(000) = 976
M_r = 450.60	D_x = 1.155 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2202 reflections
a = 10.3030 (13) Å	θ = 1.9–27.5°
b = 19.299 (3) Å	µ = 0.07 mm⁻¹
c = 13.3961 (18) Å	T = 295 K
β = 103.336 (4)°	Slab, light yellow
V = 2591.8 (6) Å³	0.56 × 0.16 × 0.10 mm
Z = 4

Data collection top

Bruker KappaAPEXII CCD diffractometer	5944 independent reflections
Radiation source: fine-focus sealed tube	3567 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω and ϕ scans	θ_max = 27.6°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→13
T_min = 0.95, T_max = 0.99	k = −23→25
17538 measured reflections	l = −17→17

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0679P)² + 0.3097P] where P = (F_o² + 2F_c²)/3
5944 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₈H₃₈N₂O₃	V = 2591.8 (6) Å³
M_r = 450.60	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.3030 (13) Å	µ = 0.07 mm⁻¹
b = 19.299 (3) Å	T = 295 K
c = 13.3961 (18) Å	0.56 × 0.16 × 0.10 mm
β = 103.336 (4)°

Data collection top

Bruker KappaAPEXII CCD diffractometer	5944 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3567 reflections with I > 2σ(I)
T_min = 0.95, T_max = 0.99	R_int = 0.041
17538 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.01	Δρ_max = 0.23 e Å⁻³
5944 reflections	Δρ_min = −0.16 e Å⁻³
298 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
O1	0.88988 (15)	0.24189 (8)	0.17052 (12)	0.0631 (5)
O2	0.50984 (16)	0.38481 (8)	0.19363 (11)	0.0601 (4)
O3	0.32638 (16)	0.06075 (9)	0.00092 (12)	0.0715 (5)
N1	0.69322 (16)	0.22382 (8)	0.45422 (12)	0.0417 (4)
N2	0.5859 (2)	0.10112 (10)	0.63649 (14)	0.0637 (5)
C1	0.78666 (19)	0.20226 (10)	0.39984 (15)	0.0410 (5)
C2	0.8942 (2)	0.15337 (11)	0.45263 (16)	0.0528 (6)
H2A	0.8534	0.1155	0.4819	0.063*
H2B	0.9530	0.1777	0.5087	0.063*
C3	0.9777 (2)	0.12330 (13)	0.38223 (18)	0.0655 (7)
C4	1.0128 (2)	0.18105 (14)	0.31611 (18)	0.0680 (7)
H4A	1.0704	0.2141	0.3597	0.082*
H4B	1.0621	0.1617	0.2691	0.082*
C5	0.8921 (2)	0.21803 (11)	0.25587 (17)	0.0486 (5)
C6	0.78033 (19)	0.22640 (10)	0.30388 (14)	0.0404 (5)
C7	1.1063 (3)	0.0932 (2)	0.4501 (2)	0.1156 (13)
H7A	1.1604	0.0739	0.4075	0.173*
H7B	1.0840	0.0576	0.4933	0.173*
H7C	1.1549	0.1294	0.4920	0.173*
C8	0.8996 (3)	0.06640 (14)	0.3143 (2)	0.0950 (10)
H8A	0.9527	0.0481	0.2702	0.143*
H8B	0.8186	0.0854	0.2734	0.143*
H8C	0.8786	0.0299	0.3567	0.143*
C9	0.65777 (19)	0.26291 (9)	0.24426 (14)	0.0394 (5)
H9	0.6859	0.2967	0.1988	0.047*
C10	0.59692 (19)	0.30198 (10)	0.31887 (14)	0.0384 (4)
C11	0.5246 (2)	0.36554 (10)	0.28247 (15)	0.0436 (5)
C12	0.4725 (2)	0.40739 (11)	0.35877 (16)	0.0549 (6)
H12A	0.3988	0.4358	0.3227	0.066*
H12B	0.5422	0.4382	0.3946	0.066*
C13	0.4252 (2)	0.36234 (11)	0.43689 (16)	0.0506 (5)
C14	0.5418 (2)	0.31647 (10)	0.48961 (15)	0.0470 (5)
H14A	0.6068	0.3449	0.5359	0.056*
H14B	0.5093	0.2820	0.5306	0.056*
C15	0.61041 (19)	0.27989 (9)	0.41677 (14)	0.0389 (4)
C16	0.3845 (3)	0.40841 (12)	0.51759 (19)	0.0737 (8)
H16A	0.3542	0.3799	0.5664	0.111*
H16B	0.3140	0.4389	0.4847	0.111*
H16C	0.4599	0.4353	0.5524	0.111*
C17	0.3062 (2)	0.31810 (13)	0.3845 (2)	0.0692 (7)
H17A	0.3313	0.2889	0.3341	0.104*
H17B	0.2340	0.3477	0.3516	0.104*
H17C	0.2783	0.2899	0.4347	0.104*
C18	0.6893 (2)	0.19211 (11)	0.55353 (15)	0.0484 (5)
H18A	0.6770	0.2280	0.6011	0.058*
H18B	0.7737	0.1693	0.5818	0.058*
C19	0.5771 (2)	0.13980 (12)	0.54196 (17)	0.0599 (6)
H19A	0.4921	0.1637	0.5239	0.072*
H19B	0.5815	0.1079	0.4869	0.072*
C20	0.4552 (3)	0.08163 (17)	0.6512 (2)	0.1008 (11)
H20A	0.4654	0.0565	0.7144	0.151*
H20B	0.4108	0.0529	0.5952	0.151*
H20C	0.4032	0.1226	0.6537	0.151*
C21	0.6703 (3)	0.04104 (14)	0.6416 (2)	0.0922 (9)
H21A	0.6759	0.0175	0.7056	0.138*
H21B	0.7579	0.0553	0.6366	0.138*
H21C	0.6334	0.0103	0.5859	0.138*
C22	0.56405 (19)	0.21121 (9)	0.17768 (14)	0.0389 (4)
C23	0.5755 (2)	0.19818 (11)	0.07903 (15)	0.0497 (5)
H23	0.6375	0.2232	0.0531	0.060*
C24	0.4982 (2)	0.14919 (11)	0.01715 (16)	0.0544 (6)
H24	0.5080	0.1420	−0.0494	0.065*
C25	0.4071 (2)	0.11125 (11)	0.05418 (16)	0.0495 (5)
C26	0.3929 (2)	0.12379 (12)	0.15253 (17)	0.0595 (6)
H26	0.3306	0.0988	0.1782	0.071*
C27	0.4700 (2)	0.17284 (11)	0.21265 (16)	0.0529 (6)
H27	0.4589	0.1805	0.2787	0.063*
C28	0.3427 (3)	0.04469 (14)	−0.09916 (19)	0.0768 (8)
H28A	0.2812	0.0088	−0.1286	0.115*
H28B	0.4323	0.0291	−0.0949	0.115*
H28C	0.3256	0.0853	−0.1415	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0671 (11)	0.0764 (11)	0.0546 (10)	−0.0024 (8)	0.0320 (8)	0.0013 (8)
O2	0.0815 (12)	0.0558 (9)	0.0444 (9)	0.0103 (8)	0.0171 (8)	0.0126 (7)
O3	0.0749 (11)	0.0787 (12)	0.0624 (11)	−0.0261 (9)	0.0192 (9)	−0.0271 (9)
N1	0.0492 (10)	0.0449 (9)	0.0323 (8)	0.0027 (8)	0.0120 (8)	0.0030 (7)
N2	0.0791 (14)	0.0595 (12)	0.0561 (12)	−0.0048 (10)	0.0231 (11)	0.0131 (10)
C1	0.0421 (11)	0.0415 (11)	0.0379 (11)	−0.0038 (8)	0.0065 (9)	−0.0051 (9)
C2	0.0551 (14)	0.0569 (13)	0.0424 (12)	0.0084 (11)	0.0031 (10)	−0.0024 (10)
C3	0.0672 (16)	0.0759 (17)	0.0521 (14)	0.0281 (13)	0.0111 (12)	−0.0006 (13)
C4	0.0499 (14)	0.097 (2)	0.0589 (15)	0.0114 (13)	0.0163 (12)	−0.0108 (14)
C5	0.0497 (13)	0.0510 (13)	0.0477 (13)	−0.0080 (10)	0.0167 (10)	−0.0124 (10)
C6	0.0443 (11)	0.0391 (11)	0.0388 (11)	−0.0044 (8)	0.0115 (9)	−0.0060 (8)
C7	0.099 (2)	0.165 (3)	0.084 (2)	0.078 (2)	0.0213 (19)	0.014 (2)
C8	0.152 (3)	0.0593 (17)	0.0743 (19)	0.0223 (18)	0.027 (2)	−0.0124 (15)
C9	0.0482 (12)	0.0392 (10)	0.0335 (10)	−0.0023 (9)	0.0147 (9)	0.0032 (8)
C10	0.0462 (11)	0.0364 (10)	0.0339 (10)	−0.0032 (8)	0.0117 (9)	−0.0009 (8)
C11	0.0496 (12)	0.0409 (11)	0.0407 (11)	−0.0041 (9)	0.0115 (10)	0.0018 (9)
C12	0.0716 (15)	0.0449 (12)	0.0517 (13)	0.0103 (11)	0.0212 (12)	0.0036 (10)
C13	0.0637 (14)	0.0461 (12)	0.0474 (12)	0.0084 (10)	0.0238 (11)	−0.0018 (10)
C14	0.0610 (14)	0.0462 (12)	0.0366 (11)	−0.0033 (10)	0.0172 (10)	−0.0052 (9)
C15	0.0426 (11)	0.0368 (11)	0.0381 (11)	−0.0044 (8)	0.0110 (9)	−0.0015 (8)
C16	0.105 (2)	0.0610 (15)	0.0668 (17)	0.0224 (14)	0.0435 (16)	0.0001 (13)
C17	0.0590 (16)	0.0802 (18)	0.0734 (17)	−0.0012 (13)	0.0257 (13)	−0.0027 (14)
C18	0.0582 (13)	0.0523 (13)	0.0350 (11)	0.0042 (10)	0.0116 (10)	0.0080 (9)
C19	0.0642 (15)	0.0624 (15)	0.0540 (14)	−0.0022 (12)	0.0153 (12)	0.0129 (11)
C20	0.109 (2)	0.103 (2)	0.111 (3)	−0.0014 (19)	0.066 (2)	0.021 (2)
C21	0.094 (2)	0.077 (2)	0.102 (2)	0.0129 (17)	0.0145 (18)	0.0305 (17)
C22	0.0430 (11)	0.0408 (11)	0.0327 (10)	0.0047 (8)	0.0081 (9)	0.0014 (8)
C23	0.0547 (13)	0.0582 (13)	0.0395 (12)	−0.0091 (10)	0.0175 (10)	−0.0032 (10)
C24	0.0597 (14)	0.0679 (15)	0.0378 (12)	−0.0049 (12)	0.0156 (11)	−0.0132 (11)
C25	0.0496 (13)	0.0505 (12)	0.0465 (12)	−0.0045 (10)	0.0073 (10)	−0.0083 (10)
C26	0.0674 (16)	0.0640 (15)	0.0511 (13)	−0.0199 (12)	0.0221 (12)	−0.0038 (11)
C27	0.0676 (15)	0.0588 (14)	0.0356 (11)	−0.0114 (11)	0.0189 (11)	−0.0028 (10)
C28	0.0816 (19)	0.0837 (19)	0.0629 (16)	−0.0160 (15)	0.0124 (14)	−0.0311 (14)

Geometric parameters (Å, º) top

O1—C5	1.228 (2)	C12—H12B	0.9700
O2—C11	1.222 (2)	C13—C17	1.526 (3)
O3—C25	1.370 (2)	C13—C14	1.528 (3)
O3—C28	1.423 (3)	C13—C16	1.531 (3)
N1—C15	1.398 (2)	C14—C15	1.506 (2)
N1—C1	1.398 (2)	C14—H14A	0.9700
N1—C18	1.473 (2)	C14—H14B	0.9700
N2—C21	1.442 (3)	C16—H16A	0.9600
N2—C20	1.454 (3)	C16—H16B	0.9600
N2—C19	1.455 (3)	C16—H16C	0.9600
C1—C6	1.355 (3)	C17—H17A	0.9600
C1—C2	1.502 (3)	C17—H17B	0.9600
C2—C3	1.529 (3)	C17—H17C	0.9600
C2—H2A	0.9700	C18—C19	1.515 (3)
C2—H2B	0.9700	C18—H18A	0.9700
C3—C4	1.518 (3)	C18—H18B	0.9700
C3—C8	1.531 (4)	C19—H19A	0.9700
C3—C7	1.538 (3)	C19—H19B	0.9700
C4—C5	1.498 (3)	C20—H20A	0.9600
C4—H4A	0.9700	C20—H20B	0.9600
C4—H4B	0.9700	C20—H20C	0.9600
C5—C6	1.452 (3)	C21—H21A	0.9600
C6—C9	1.505 (3)	C21—H21B	0.9600
C7—H7A	0.9600	C21—H21C	0.9600
C7—H7B	0.9600	C22—C23	1.377 (2)
C7—H7C	0.9600	C22—C27	1.384 (3)
C8—H8A	0.9600	C23—C24	1.382 (3)
C8—H8B	0.9600	C23—H23	0.9300
C8—H8C	0.9600	C24—C25	1.370 (3)
C9—C10	1.500 (2)	C24—H24	0.9300
C9—C22	1.525 (3)	C25—C26	1.380 (3)
C9—H9	0.9800	C26—C27	1.372 (3)
C10—C15	1.355 (2)	C26—H26	0.9300
C10—C11	1.459 (3)	C27—H27	0.9300
C11—C12	1.496 (3)	C28—H28A	0.9600
C12—C13	1.524 (3)	C28—H28B	0.9600
C12—H12A	0.9700	C28—H28C	0.9600

C25—O3—C28	117.13 (18)	C15—C14—C13	114.11 (16)
C15—N1—C1	118.69 (15)	C15—C14—H14A	108.7
C15—N1—C18	120.27 (15)	C13—C14—H14A	108.7
C1—N1—C18	120.84 (16)	C15—C14—H14B	108.7
C21—N2—C20	110.7 (2)	C13—C14—H14B	108.7
C21—N2—C19	111.7 (2)	H14A—C14—H14B	107.6
C20—N2—C19	112.2 (2)	C10—C15—N1	120.58 (16)
C6—C1—N1	120.26 (18)	C10—C15—C14	121.39 (17)
C6—C1—C2	122.10 (17)	N1—C15—C14	117.98 (16)
N1—C1—C2	117.62 (16)	C13—C16—H16A	109.5
C1—C2—C3	114.00 (17)	C13—C16—H16B	109.5
C1—C2—H2A	108.8	H16A—C16—H16B	109.5
C3—C2—H2A	108.8	C13—C16—H16C	109.5
C1—C2—H2B	108.8	H16A—C16—H16C	109.5
C3—C2—H2B	108.8	H16B—C16—H16C	109.5
H2A—C2—H2B	107.6	C13—C17—H17A	109.5
C4—C3—C2	108.96 (19)	C13—C17—H17B	109.5
C4—C3—C8	110.1 (2)	H17A—C17—H17B	109.5
C2—C3—C8	110.2 (2)	C13—C17—H17C	109.5
C4—C3—C7	109.5 (2)	H17A—C17—H17C	109.5
C2—C3—C7	107.98 (19)	H17B—C17—H17C	109.5
C8—C3—C7	110.1 (2)	N1—C18—C19	111.32 (17)
C5—C4—C3	112.6 (2)	N1—C18—H18A	109.4
C5—C4—H4A	109.1	C19—C18—H18A	109.4
C3—C4—H4A	109.1	N1—C18—H18B	109.4
C5—C4—H4B	109.1	C19—C18—H18B	109.4
C3—C4—H4B	109.1	H18A—C18—H18B	108.0
H4A—C4—H4B	107.8	N2—C19—C18	111.11 (18)
O1—C5—C6	121.6 (2)	N2—C19—H19A	109.4
O1—C5—C4	121.02 (19)	C18—C19—H19A	109.4
C6—C5—C4	117.34 (19)	N2—C19—H19B	109.4
C1—C6—C5	120.83 (19)	C18—C19—H19B	109.4
C1—C6—C9	121.04 (17)	H19A—C19—H19B	108.0
C5—C6—C9	118.13 (17)	N2—C20—H20A	109.5
C3—C7—H7A	109.5	N2—C20—H20B	109.5
C3—C7—H7B	109.5	H20A—C20—H20B	109.5
H7A—C7—H7B	109.5	N2—C20—H20C	109.5
C3—C7—H7C	109.5	H20A—C20—H20C	109.5
H7A—C7—H7C	109.5	H20B—C20—H20C	109.5
H7B—C7—H7C	109.5	N2—C21—H21A	109.5
C3—C8—H8A	109.5	N2—C21—H21B	109.5
C3—C8—H8B	109.5	H21A—C21—H21B	109.5
H8A—C8—H8B	109.5	N2—C21—H21C	109.5
C3—C8—H8C	109.5	H21A—C21—H21C	109.5
H8A—C8—H8C	109.5	H21B—C21—H21C	109.5
H8B—C8—H8C	109.5	C23—C22—C27	116.67 (18)
C10—C9—C6	108.08 (15)	C23—C22—C9	119.86 (17)
C10—C9—C22	114.40 (15)	C27—C22—C9	123.38 (16)
C6—C9—C22	110.16 (15)	C22—C23—C24	122.36 (19)
C10—C9—H9	108.0	C22—C23—H23	118.8
C6—C9—H9	108.0	C24—C23—H23	118.8
C22—C9—H9	108.0	C25—C24—C23	119.76 (19)
C15—C10—C11	121.21 (17)	C25—C24—H24	120.1
C15—C10—C9	121.43 (17)	C23—C24—H24	120.1
C11—C10—C9	117.35 (16)	O3—C25—C24	125.15 (19)
O2—C11—C10	121.36 (17)	O3—C25—C26	115.88 (19)
O2—C11—C12	121.14 (18)	C24—C25—C26	119.0 (2)
C10—C11—C12	117.48 (17)	C27—C26—C25	120.4 (2)
C11—C12—C13	112.51 (17)	C27—C26—H26	119.8
C11—C12—H12A	109.1	C25—C26—H26	119.8
C13—C12—H12A	109.1	C26—C27—C22	121.77 (19)
C11—C12—H12B	109.1	C26—C27—H27	119.1
C13—C12—H12B	109.1	C22—C27—H27	119.1
H12A—C12—H12B	107.8	O3—C28—H28A	109.5
C12—C13—C17	110.69 (19)	O3—C28—H28B	109.5
C12—C13—C14	107.84 (17)	H28A—C28—H28B	109.5
C17—C13—C14	110.58 (18)	O3—C28—H28C	109.5
C12—C13—C16	109.66 (17)	H28A—C28—H28C	109.5
C17—C13—C16	109.12 (19)	H28B—C28—H28C	109.5
C14—C13—C16	108.92 (18)

C15—N1—C1—C6	−12.1 (3)	C11—C12—C13—C14	56.7 (2)
C18—N1—C1—C6	172.94 (18)	C11—C12—C13—C16	175.2 (2)
C15—N1—C1—C2	166.47 (18)	C12—C13—C14—C15	−48.6 (2)
C18—N1—C1—C2	−8.4 (3)	C17—C13—C14—C15	72.5 (2)
C6—C1—C2—C3	−10.9 (3)	C16—C13—C14—C15	−167.55 (18)
N1—C1—C2—C3	170.49 (18)	C11—C10—C15—N1	−172.16 (17)
C1—C2—C3—C4	44.3 (3)	C9—C10—C15—N1	6.7 (3)
C1—C2—C3—C8	−76.6 (3)	C11—C10—C15—C14	5.2 (3)
C1—C2—C3—C7	163.1 (2)	C9—C10—C15—C14	−175.93 (17)
C2—C3—C4—C5	−56.0 (3)	C1—N1—C15—C10	16.1 (3)
C8—C3—C4—C5	64.9 (3)	C18—N1—C15—C10	−168.99 (18)
C7—C3—C4—C5	−173.9 (2)	C1—N1—C15—C14	−161.44 (16)
C3—C4—C5—O1	−147.1 (2)	C18—N1—C15—C14	13.5 (3)
C3—C4—C5—C6	34.8 (3)	C13—C14—C15—C10	19.1 (3)
N1—C1—C6—C5	165.40 (17)	C13—C14—C15—N1	−163.47 (17)
C2—C1—C6—C5	−13.2 (3)	C15—N1—C18—C19	83.4 (2)
N1—C1—C6—C9	−14.3 (3)	C1—N1—C18—C19	−101.7 (2)
C2—C1—C6—C9	167.16 (17)	C21—N2—C19—C18	−87.4 (2)
O1—C5—C6—C1	−177.22 (19)	C20—N2—C19—C18	147.7 (2)
C4—C5—C6—C1	0.8 (3)	N1—C18—C19—N2	171.31 (17)
O1—C5—C6—C9	2.5 (3)	C10—C9—C22—C23	147.68 (18)
C4—C5—C6—C9	−179.53 (18)	C6—C9—C22—C23	−90.4 (2)
C1—C6—C9—C10	33.0 (2)	C10—C9—C22—C27	−35.8 (3)
C5—C6—C9—C10	−146.74 (17)	C6—C9—C22—C27	86.2 (2)
C1—C6—C9—C22	−92.7 (2)	C27—C22—C23—C24	−0.3 (3)
C5—C6—C9—C22	87.62 (19)	C9—C22—C23—C24	176.46 (19)
C6—C9—C10—C15	−29.1 (2)	C22—C23—C24—C25	−0.6 (3)
C22—C9—C10—C15	94.0 (2)	C28—O3—C25—C24	2.7 (3)
C6—C9—C10—C11	149.79 (16)	C28—O3—C25—C26	−177.5 (2)
C22—C9—C10—C11	−87.1 (2)	C23—C24—C25—O3	−179.0 (2)
C15—C10—C11—O2	−178.41 (19)	C23—C24—C25—C26	1.2 (3)
C9—C10—C11—O2	2.7 (3)	O3—C25—C26—C27	179.3 (2)
C15—C10—C11—C12	3.3 (3)	C24—C25—C26—C27	−0.8 (4)
C9—C10—C11—C12	−175.59 (17)	C25—C26—C27—C22	−0.1 (4)
O2—C11—C12—C13	146.1 (2)	C23—C22—C27—C26	0.6 (3)
C10—C11—C12—C13	−35.6 (3)	C9—C22—C27—C26	−176.0 (2)
C11—C12—C13—C17	−64.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O1ⁱ	0.97	2.51	3.368 (2)	147

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

Experimental details

Crystal data
Chemical formula	C₂₈H₃₈N₂O₃
M_r	450.60
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	10.3030 (13), 19.299 (3), 13.3961 (18)
β (°)	103.336 (4)
V (Å³)	2591.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.56 × 0.16 × 0.10

Data collection
Diffractometer	Bruker KappaAPEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.95, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	17538, 5944, 3567
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.162, 1.01
No. of reflections	5944
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.16

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O1ⁱ	0.97	2.51	3.368 (2)	147

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

Acknowledgements

The authors thank Professor P. Ramamurthy, National Centre for Ultrafast Processes, University of Madras, Taramani Campus, Chennai 600 113, India, for his help during the preparation of the sample.

References

Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Josephrajan, T., Ramakrishnan, V. T., Kathiravan, G. & Muthumary, J. (2005). ARKIVOC, pp. 124–136. Google Scholar
Murugan, P., Shanmugasundaram, P., Ramakrishnan, V. T., Venkatachalapathy, B., Srividya, N., Ramamurthy, P., Gunasekaran, K. & Velmurugan, D. (1998). J. Chem. Soc. Perkin Trans. 2, pp. 999–1003. Web of Science CSD CrossRef Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Srividya, N., Ramamurthy, P. & Ramakrishnan, V. T. (1998). Spectrochim. Acta Part A, 54, 245–253. Web of Science CrossRef Google Scholar
Srividya, N., Ramamurthy, P., Shanmugasundaram, P. & Ramakrishnan, V. T. (1996). J. Org. Chem. 61, 5083–5089. CrossRef CAS Web of Science Google Scholar

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Volume 65| Part 2| February 2009| Page o271

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

10-[2-(Di­methyl­amino)eth­yl]-9-(4-meth­oxy­phen­yl)-3,3,6,6-tetra­methyl-3,4,6,7,9,10-hexa­hydro­acridine-1,8(2H,5H)-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

10-[2-(Dimethylamino)ethyl]-9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione