9-(4-Hy-droxy-3-meth-oxy-phen-yl)-3,3,6,6-tetra-methyl-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione.

In the title mol-ecule, C24H29NO4, the central ring of the acridinedione system adopts a flat boat conformation and the four essentially planar atoms of this ring [maximum deviation = 0.001 (2) Å] form a dihedral angle of 85.99 (12)° with the benzene ring. The two outer rings of the acridinedione system adopt sofa conformations. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules, forming a two-dimensional network parallel to (100).

Related literature

For applications of acridines, see: Murugan et al. (1998 ▶); Josephrajan et al. (2005 ▶); Srividya et al. (1998 ▶,1996 ▶). For related structures, see: Balamurugan et al. (2009 ▶); Zhao & Teng (2008 ▶). For ring conformations, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C24H29NO4

M = 395.48

Monoclinic,

a = 10.4828 (3) Å

b = 14.8973 (4) Å

c = 14.2059 (3) Å

β = 101.609 (2)°

V = 2173.09 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.970, T max = 1.000

63634 measured reflections

4264 independent reflections

2958 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.116

S = 1.02

4264 reflections

267 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050568/lh5567sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050568/lh5567Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050568/lh5567Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H29NO4	F(000) = 848
Mr = 395.48	Dx = 1.209 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 22356 reflections
a = 10.4828 (3) Å	θ = 3.5–29.2°
b = 14.8973 (4) Å	µ = 0.08 mm−1
c = 14.2059 (3) Å	T = 293 K
β = 101.609 (2)°	Block, yellow
V = 2173.09 (10) Å3	0.3 × 0.2 × 0.2 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4264 independent reflections
Radiation source: fine-focus sealed tube	2958 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.078
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.5°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −18→18
Tmin = 0.970, Tmax = 1.000	l = −17→17
63634 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0342P)2 + 1.3025P] where P = (Fo2 + 2Fc2)/3
4264 reflections	(Δ/σ)max = 0.001
267 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	Uiso*/Ueq
O1	0.36588 (15)	0.71186 (11)	0.15883 (12)	0.0579 (5)
H1	0.3497	0.6666	0.1872	0.087*
O2	0.50253 (16)	0.63379 (12)	0.31829 (13)	0.0679 (6)
O3	0.98444 (15)	0.78678 (10)	0.20508 (10)	0.0449 (4)
O4	0.74288 (15)	1.04026 (10)	0.34010 (10)	0.0474 (4)
C1	1.01925 (19)	0.76067 (13)	0.28878 (14)	0.0324 (5)
C2	1.1273 (2)	0.69369 (16)	0.31500 (15)	0.0443 (6)
H2A	1.2095	0.7257	0.3296	0.053*
H2B	1.1287	0.6558	0.2597	0.053*
C3	1.1169 (2)	0.63400 (15)	0.40043 (15)	0.0414 (5)
C4	1.0993 (2)	0.69384 (14)	0.48413 (14)	0.0365 (5)
H4A	1.0735	0.6569	0.5333	0.044*
H4B	1.1821	0.7215	0.5118	0.044*
C4A	0.99980 (18)	0.76586 (13)	0.45531 (13)	0.0282 (4)
C5	0.86618 (19)	0.92717 (14)	0.60844 (13)	0.0340 (5)
H5A	0.9431	0.9626	0.6337	0.041*
H5B	0.8581	0.8815	0.6556	0.041*
C5A	0.88328 (18)	0.88242 (13)	0.51737 (13)	0.0281 (4)
C6	0.74670 (19)	0.98788 (14)	0.59372 (15)	0.0364 (5)
C7	0.7532 (2)	1.04984 (13)	0.50920 (14)	0.0354 (5)
H7A	0.6723	1.0833	0.4935	0.043*
H7B	0.8229	1.0928	0.5294	0.043*
C8	0.77544 (18)	1.00365 (13)	0.41909 (14)	0.0312 (5)
C8A	0.83906 (18)	0.91691 (13)	0.42877 (13)	0.0277 (4)
C9	0.85163 (18)	0.86508 (12)	0.33895 (12)	0.0279 (4)
H9	0.8768	0.9076	0.2933	0.033*
C9A	0.95946 (18)	0.79613 (13)	0.36429 (13)	0.0276 (4)
N10	0.95340 (15)	0.80412 (11)	0.52928 (11)	0.0325 (4)
H10	0.9686	0.7784	0.5846	0.039*
C11	1.0003 (3)	0.57076 (16)	0.37230 (17)	0.0570 (7)
H11A	0.9227	0.6054	0.3505	0.085*
H11B	0.9906	0.5356	0.4271	0.085*
H11C	1.0144	0.5316	0.3217	0.085*
C12	1.2408 (3)	0.5783 (2)	0.43053 (19)	0.0732 (9)
H12A	1.2543	0.5424	0.3772	0.110*
H12B	1.2321	0.5399	0.4831	0.110*
H12C	1.3138	0.6176	0.4502	0.110*
C13	0.6240 (2)	0.92964 (19)	0.57391 (19)	0.0600 (7)
H13A	0.5489	0.9666	0.5736	0.090*
H13B	0.6297	0.8848	0.6231	0.090*
H13C	0.6163	0.9009	0.5125	0.090*
C14	0.7475 (3)	1.04393 (17)	0.68425 (17)	0.0587 (7)
H14A	0.8277	1.0769	0.7002	0.088*
H14B	0.7398	1.0049	0.7366	0.088*
H14C	0.6756	1.0851	0.6727	0.088*
C15	0.72117 (19)	0.82284 (13)	0.29120 (13)	0.0311 (5)
C16	0.6463 (2)	0.85976 (16)	0.21025 (17)	0.0591 (8)
H16	0.6756	0.9107	0.1832	0.071*
C17	0.5277 (3)	0.82234 (17)	0.16818 (18)	0.0640 (8)
H17	0.4781	0.8491	0.1138	0.077*
C18	0.4818 (2)	0.74704 (14)	0.20478 (15)	0.0393 (5)
C19	0.5562 (2)	0.70943 (14)	0.28684 (15)	0.0370 (5)
C20	0.67392 (19)	0.74706 (14)	0.32934 (14)	0.0362 (5)
H20	0.7225	0.7211	0.3846	0.043*
C21	0.5784 (3)	0.58366 (18)	0.3926 (2)	0.0686 (8)
H21A	0.6595	0.5680	0.3752	0.103*
H21B	0.5326	0.5299	0.4029	0.103*
H21C	0.5952	0.6187	0.4505	0.103*

	U11	U22	U33	U12	U13	U23
O1	0.0465 (10)	0.0494 (10)	0.0643 (11)	−0.0135 (8)	−0.0210 (8)	0.0109 (8)
O2	0.0477 (10)	0.0733 (12)	0.0732 (12)	−0.0243 (9)	−0.0107 (9)	0.0376 (10)
O3	0.0643 (10)	0.0500 (9)	0.0211 (8)	−0.0007 (8)	0.0103 (7)	−0.0018 (7)
O4	0.0625 (10)	0.0403 (9)	0.0365 (9)	0.0105 (8)	0.0028 (7)	0.0104 (7)
C1	0.0378 (11)	0.0354 (11)	0.0240 (10)	−0.0080 (9)	0.0061 (8)	−0.0028 (9)
C2	0.0458 (13)	0.0560 (14)	0.0338 (12)	0.0059 (11)	0.0144 (10)	−0.0080 (11)
C3	0.0459 (13)	0.0448 (13)	0.0310 (11)	0.0142 (11)	0.0019 (9)	−0.0036 (10)
C4	0.0364 (11)	0.0445 (12)	0.0262 (11)	0.0079 (10)	0.0002 (8)	−0.0001 (9)
C4A	0.0280 (10)	0.0327 (11)	0.0233 (10)	−0.0011 (8)	0.0040 (8)	−0.0022 (8)
C5	0.0342 (11)	0.0421 (12)	0.0245 (10)	0.0040 (9)	0.0032 (8)	−0.0001 (9)
C5A	0.0272 (10)	0.0317 (10)	0.0250 (10)	−0.0007 (8)	0.0043 (8)	0.0000 (8)
C6	0.0327 (11)	0.0422 (12)	0.0352 (11)	0.0048 (10)	0.0091 (9)	0.0032 (9)
C7	0.0324 (11)	0.0332 (11)	0.0404 (12)	0.0022 (9)	0.0069 (9)	0.0003 (9)
C8	0.0262 (10)	0.0319 (11)	0.0333 (11)	−0.0045 (9)	0.0005 (8)	0.0041 (9)
C8A	0.0271 (10)	0.0298 (10)	0.0250 (10)	−0.0025 (8)	0.0026 (8)	0.0015 (8)
C9	0.0328 (10)	0.0291 (10)	0.0203 (9)	−0.0022 (8)	0.0020 (8)	0.0047 (8)
C9A	0.0291 (10)	0.0313 (10)	0.0215 (9)	−0.0037 (8)	0.0027 (7)	−0.0014 (8)
N10	0.0404 (10)	0.0383 (10)	0.0185 (8)	0.0082 (8)	0.0057 (7)	0.0056 (7)
C11	0.0828 (19)	0.0430 (14)	0.0410 (14)	−0.0041 (13)	0.0027 (13)	−0.0003 (11)
C12	0.080 (2)	0.083 (2)	0.0525 (16)	0.0469 (17)	0.0048 (14)	−0.0075 (15)
C13	0.0364 (13)	0.0738 (18)	0.0707 (18)	−0.0037 (13)	0.0128 (12)	0.0242 (14)
C14	0.0721 (18)	0.0621 (16)	0.0480 (15)	0.0236 (14)	0.0269 (13)	0.0006 (12)
C15	0.0354 (11)	0.0303 (11)	0.0244 (10)	−0.0007 (9)	−0.0016 (8)	−0.0002 (8)
C16	0.0675 (17)	0.0463 (14)	0.0490 (15)	−0.0251 (13)	−0.0232 (12)	0.0232 (11)
C17	0.0661 (17)	0.0524 (15)	0.0542 (16)	−0.0174 (13)	−0.0341 (13)	0.0244 (13)
C18	0.0362 (12)	0.0345 (11)	0.0408 (12)	−0.0028 (10)	−0.0072 (9)	−0.0011 (10)
C19	0.0345 (11)	0.0377 (12)	0.0375 (12)	−0.0035 (9)	0.0039 (9)	0.0061 (9)
C20	0.0352 (11)	0.0430 (12)	0.0274 (11)	−0.0003 (10)	−0.0008 (8)	0.0114 (9)
C21	0.0579 (17)	0.0636 (18)	0.083 (2)	−0.0048 (14)	0.0111 (14)	0.0390 (16)

O1—C18	1.364 (2)	C8—C8A	1.448 (3)
O1—H1	0.8200	C8A—C9	1.520 (3)
O2—C19	1.374 (2)	C9—C9A	1.516 (3)
O2—C21	1.403 (3)	C9—C15	1.534 (3)
O3—C1	1.234 (2)	C9—H9	0.9800
O4—C8	1.232 (2)	N10—H10	0.8600
C1—C9A	1.447 (3)	C11—H11A	0.9600
C1—C2	1.499 (3)	C11—H11B	0.9600
C2—C3	1.526 (3)	C11—H11C	0.9600
C2—H2A	0.9700	C12—H12A	0.9600
C2—H2B	0.9700	C12—H12B	0.9600
C3—C4	1.527 (3)	C12—H12C	0.9600
C3—C12	1.528 (3)	C13—H13A	0.9600
C3—C11	1.532 (3)	C13—H13B	0.9600
C4—C4A	1.495 (3)	C13—H13C	0.9600
C4—H4A	0.9700	C14—H14A	0.9600
C4—H4B	0.9700	C14—H14B	0.9600
C4A—C9A	1.354 (2)	C14—H14C	0.9600
C4A—N10	1.368 (2)	C15—C16	1.370 (3)
C5—C5A	1.498 (3)	C15—C20	1.386 (3)
C5—C6	1.525 (3)	C16—C17	1.384 (3)
C5—H5A	0.9700	C16—H16	0.9300
C5—H5B	0.9700	C17—C18	1.364 (3)
C5A—C8A	1.352 (2)	C17—H17	0.9300
C5A—N10	1.371 (2)	C18—C19	1.384 (3)
C6—C7	1.527 (3)	C19—C20	1.379 (3)
C6—C13	1.530 (3)	C20—H20	0.9300
C6—C14	1.532 (3)	C21—H21A	0.9600
C7—C8	1.512 (3)	C21—H21B	0.9600
C7—H7A	0.9700	C21—H21C	0.9600
C7—H7B	0.9700
C18—O1—H1	109.5	C8A—C9—H9	107.9
C19—O2—C21	118.32 (18)	C15—C9—H9	107.9
O3—C1—C9A	120.73 (19)	C4A—C9A—C1	119.19 (18)
O3—C1—C2	120.74 (18)	C4A—C9A—C9	121.81 (17)
C9A—C1—C2	118.50 (17)	C1—C9A—C9	119.00 (16)
C1—C2—C3	114.46 (18)	C4A—N10—C5A	121.63 (16)
C1—C2—H2A	108.6	C4A—N10—H10	119.2
C3—C2—H2A	108.6	C5A—N10—H10	119.2
C1—C2—H2B	108.6	C3—C11—H11A	109.5
C3—C2—H2B	108.6	C3—C11—H11B	109.5
H2A—C2—H2B	107.6	H11A—C11—H11B	109.5
C2—C3—C4	108.56 (18)	C3—C11—H11C	109.5
C2—C3—C12	110.3 (2)	H11A—C11—H11C	109.5
C4—C3—C12	109.17 (17)	H11B—C11—H11C	109.5
C2—C3—C11	109.39 (18)	C3—C12—H12A	109.5
C4—C3—C11	110.29 (19)	C3—C12—H12B	109.5
C12—C3—C11	109.1 (2)	H12A—C12—H12B	109.5
C4A—C4—C3	113.14 (16)	C3—C12—H12C	109.5
C4A—C4—H4A	109.0	H12A—C12—H12C	109.5
C3—C4—H4A	109.0	H12B—C12—H12C	109.5
C4A—C4—H4B	109.0	C6—C13—H13A	109.5
C3—C4—H4B	109.0	C6—C13—H13B	109.5
H4A—C4—H4B	107.8	H13A—C13—H13B	109.5
C9A—C4A—N10	120.24 (17)	C6—C13—H13C	109.5
C9A—C4A—C4	124.55 (17)	H13A—C13—H13C	109.5
N10—C4A—C4	115.15 (16)	H13B—C13—H13C	109.5
C5A—C5—C6	112.54 (16)	C6—C14—H14A	109.5
C5A—C5—H5A	109.1	C6—C14—H14B	109.5
C6—C5—H5A	109.1	H14A—C14—H14B	109.5
C5A—C5—H5B	109.1	C6—C14—H14C	109.5
C6—C5—H5B	109.1	H14A—C14—H14C	109.5
H5A—C5—H5B	107.8	H14B—C14—H14C	109.5
C8A—C5A—N10	120.88 (17)	C16—C15—C20	117.74 (19)
C8A—C5A—C5	123.82 (18)	C16—C15—C9	121.04 (18)
N10—C5A—C5	115.24 (16)	C20—C15—C9	121.21 (16)
C5—C6—C7	107.52 (16)	C15—C16—C17	120.9 (2)
C5—C6—C13	109.03 (18)	C15—C16—H16	119.5
C7—C6—C13	111.54 (18)	C17—C16—H16	119.5
C5—C6—C14	110.03 (17)	C18—C17—C16	121.4 (2)
C7—C6—C14	109.70 (18)	C18—C17—H17	119.3
C13—C6—C14	109.01 (19)	C16—C17—H17	119.3
C8—C7—C6	115.43 (17)	O1—C18—C17	118.83 (19)
C8—C7—H7A	108.4	O1—C18—C19	122.98 (19)
C6—C7—H7A	108.4	C17—C18—C19	118.19 (19)
C8—C7—H7B	108.4	O2—C19—C20	125.45 (18)
C6—C7—H7B	108.4	O2—C19—C18	114.10 (18)
H7A—C7—H7B	107.5	C20—C19—C18	120.45 (19)
O4—C8—C8A	121.28 (18)	C19—C20—C15	121.24 (18)
O4—C8—C7	120.51 (18)	C19—C20—H20	119.4
C8A—C8—C7	118.18 (17)	C15—C20—H20	119.4
C5A—C8A—C8	119.51 (18)	O2—C21—H21A	109.5
C5A—C8A—C9	121.13 (17)	O2—C21—H21B	109.5
C8—C8A—C9	119.33 (16)	H21A—C21—H21B	109.5
C9A—C9—C8A	109.35 (14)	O2—C21—H21C	109.5
C9A—C9—C15	112.51 (15)	H21A—C21—H21C	109.5
C8A—C9—C15	111.07 (15)	H21B—C21—H21C	109.5
C9A—C9—H9	107.9
O3—C1—C2—C3	−150.88 (19)	N10—C4A—C9A—C9	−7.0 (3)
C9A—C1—C2—C3	31.0 (3)	C4—C4A—C9A—C9	175.87 (18)
C1—C2—C3—C4	−52.0 (2)	O3—C1—C9A—C4A	179.86 (19)
C1—C2—C3—C12	−171.60 (19)	C2—C1—C9A—C4A	−2.1 (3)
C1—C2—C3—C11	68.3 (2)	O3—C1—C9A—C9	0.9 (3)
C2—C3—C4—C4A	46.2 (2)	C2—C1—C9A—C9	178.97 (17)
C12—C3—C4—C4A	166.4 (2)	C8A—C9—C9A—C4A	21.9 (2)
C11—C3—C4—C4A	−73.7 (2)	C15—C9—C9A—C4A	−102.0 (2)
C3—C4—C4A—C9A	−20.7 (3)	C8A—C9—C9A—C1	−159.14 (16)
C3—C4—C4A—N10	162.08 (18)	C15—C9—C9A—C1	76.9 (2)
C6—C5—C5A—C8A	26.8 (3)	C9A—C4A—N10—C5A	−11.1 (3)
C6—C5—C5A—N10	−156.02 (17)	C4—C4A—N10—C5A	166.29 (17)
C5A—C5—C6—C7	−50.7 (2)	C8A—C5A—N10—C4A	11.0 (3)
C5A—C5—C6—C13	70.3 (2)	C5—C5A—N10—C4A	−166.26 (17)
C5A—C5—C6—C14	−170.15 (18)	C9A—C9—C15—C16	−133.8 (2)
C5—C6—C7—C8	50.7 (2)	C8A—C9—C15—C16	103.3 (2)
C13—C6—C7—C8	−68.8 (2)	C9A—C9—C15—C20	47.4 (2)
C14—C6—C7—C8	170.34 (18)	C8A—C9—C15—C20	−75.6 (2)
C6—C7—C8—O4	157.24 (18)	C20—C15—C16—C17	−0.1 (4)
C6—C7—C8—C8A	−24.5 (2)	C9—C15—C16—C17	−179.0 (2)
N10—C5A—C8A—C8	−174.53 (17)	C15—C16—C17—C18	−0.9 (5)
C5—C5A—C8A—C8	2.5 (3)	C16—C17—C18—O1	−178.3 (3)
N10—C5A—C8A—C9	7.2 (3)	C16—C17—C18—C19	1.2 (4)
C5—C5A—C8A—C9	−175.83 (17)	C21—O2—C19—C20	−8.0 (4)
O4—C8—C8A—C5A	174.37 (19)	C21—O2—C19—C18	171.2 (2)
C7—C8—C8A—C5A	−3.9 (3)	O1—C18—C19—O2	−0.3 (3)
O4—C8—C8A—C9	−7.3 (3)	C17—C18—C19—O2	−179.9 (2)
C7—C8—C8A—C9	174.46 (17)	O1—C18—C19—C20	178.8 (2)
C5A—C8A—C9—C9A	−21.9 (2)	C17—C18—C19—C20	−0.7 (4)
C8—C8A—C9—C9A	159.82 (16)	O2—C19—C20—C15	178.8 (2)
C5A—C8A—C9—C15	102.9 (2)	C18—C19—C20—C15	−0.3 (3)
C8—C8A—C9—C15	−75.4 (2)	C16—C15—C20—C19	0.6 (3)
N10—C4A—C9A—C1	174.02 (17)	C9—C15—C20—C19	179.51 (19)
C4—C4A—C9A—C1	−3.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.82	2.12	2.800 (2)	141
N10—H10···O3ii	0.86	1.95	2.802 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.82	2.12	2.800 (2)	141
N10—H10⋯O3ii	0.86	1.95	2.802 (2)	174

Symmetry codes: (i) ; (ii) .