10-(2-Hy­droxy­eth­yl)-9-(2-hy­droxy­phen­yl)-3,3,6,6-tetra­methyl-1,2,3,4,5,6,7,8,9,10-deca­hydro­acridine-1,8-dione

Abdelhamid, A.A.; Mohamed, S.K.; Khalilov, A.N.; Gurbanov, A.V.; Ng, S.W.

doi:10.1107/S1600536811006969

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o744

doi:10.1107/S1600536811006969

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10-(2-Hydroxyethyl)-9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione

Antar A. Abdelhamid,^a Shaaban K. Mohamed,^b Ali N. Khalilov,^a Atash V. Gurbanov ^a and Seik Weng Ng ^c ^*

^aDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan, ^bSchool of Biology, Chemistry and Material Science, Manchester Metropolitan University, Manchester, England, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 16 February 2011; accepted 23 February 2011; online 26 February 2011)

The dihydropyridine ring in the title compound, C₂₅H₃₁NO₄, adopts an envelope conformation with the methine C atom representing the flap. The cyclohexenone rings also adopt envelope conformations with the C atoms bearing the methyl C atoms representing the flaps. The phenolic hydroxy group forms an intramolecular hydrogen bond to one of the two keto O atoms. The hydroxy group of the N-bonded alkyl chain forms an intermolecular hydrogen bond to the other keto O atom of an adjacent molecule. The latter hydrogen bond leads to the formation of a helical chain running along the b axis.

Related literature

For a related structure, see: Jang et al. (2005 ).

Experimental

Crystal data

C₂₅H₃₁NO₄
M_r = 409.51
Monoclinic, P 2₁ /n
a = 9.7037 (2) Å
b = 16.5123 (3) Å
c = 13.8847 (3) Å
β = 102.132 (3)°
V = 2175.06 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.979, T_max = 0.988
19082 measured reflections
4915 independent reflections
3770 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.123
S = 1.03
4915 reflections
279 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.84 (1)	1.84 (1)	2.659 (2)	166 (2)
O4—H4⋯O3ⁱ	0.85 (1)	1.98 (1)	2.818 (2)	166 (2)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006969/im2270sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006969/im2270Isup2.hkl

checkCIF report

Comment top

Substituted benzaldehydes react with dimedone along with a primary amine to yield N-substituted 1,2,3,4,5,6,7,8,9,10-decahydro-acridine-1,8-diones. The title compound has a hydroxy group in 2-position of the aromatic ring. This permits intramolecular hydrogen bonding, a feature also noted in the related 9-(2,6-dihydroxyphenyl)-3,3,6,6-tetramethyl-N-(4-methylphenyl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-decahydroacridine (Jang et al., 2005). The second hydroxy unit in this case engages in intermolecular hydrogen bonding to afford a centrosymmetric dimer. The title compound (Scheme I, Fig. 1) has another hydroxy unit in the N bonded hydroxyethyl substituent. This groups engages in intermolecular hydrogen bond furnishing a linear chain that runs along the c-axis of the monoclinic unit cell.

Related literature top

For a related structure, see: Jang et al. (2005).

Experimental top

Dimedone (20 mmol), salicylic aldehyde (10 mmol) and 2-amino-ethanol (10 mmol) were heated in ethanol (100 ml) for 5 h. After cooling the solution the product was collected by filtration and crystallized from ethanol; m.p. 462 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₅H₃₁NO₄ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

10-(2-Hydroxyethyl)-9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl- 1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione top

Crystal data top

C₂₅H₃₁NO₄	F(000) = 880
M_r = 409.51	D_x = 1.251 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6079 reflections
a = 9.7037 (2) Å	θ = 2.3–29.4°
b = 16.5123 (3) Å	µ = 0.08 mm⁻¹
c = 13.8847 (3) Å	T = 100 K
β = 102.132 (3)°	Irregular block, light yellow
V = 2175.06 (8) Å³	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4915 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3770 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.042
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −21→21
T_min = 0.979, T_max = 0.988	l = −18→18
19082 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0517P)² + 0.8053P] where P = (F_o² + 2F_c²)/3
4915 reflections	(Δ/σ)_max = 0.001
279 parameters	Δρ_max = 0.27 e Å⁻³
2 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₅H₃₁NO₄	V = 2175.06 (8) Å³
M_r = 409.51	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.7037 (2) Å	µ = 0.08 mm⁻¹
b = 16.5123 (3) Å	T = 100 K
c = 13.8847 (3) Å	0.25 × 0.20 × 0.15 mm
β = 102.132 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4915 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3770 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.988	R_int = 0.042
19082 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	2 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.27 e Å⁻³
4915 reflections	Δρ_min = −0.26 e Å⁻³
279 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.48778 (12)	0.25598 (7)	0.49186 (8)	0.0245 (3)
O2	0.71758 (12)	0.26499 (7)	0.63474 (8)	0.0239 (3)
O3	0.32877 (12)	0.07916 (7)	0.64843 (8)	0.0252 (3)
O4	0.36042 (14)	0.44954 (8)	0.90598 (10)	0.0357 (3)
N1	0.45983 (13)	0.28498 (7)	0.88782 (9)	0.0174 (3)
C1	0.37807 (16)	0.29121 (9)	0.52419 (11)	0.0198 (3)
C2	0.28360 (17)	0.33708 (10)	0.45699 (12)	0.0242 (4)
H2	0.2980	0.3443	0.3919	0.029*
C3	0.16843 (17)	0.37236 (10)	0.48466 (12)	0.0245 (4)
H3	0.1030	0.4030	0.4382	0.029*
C4	0.14843 (17)	0.36311 (9)	0.57997 (12)	0.0232 (4)
H4A	0.0701	0.3878	0.5993	0.028*
C5	0.24353 (16)	0.31759 (9)	0.64673 (11)	0.0201 (3)
H5	0.2297	0.3118	0.7121	0.024*
C6	0.35895 (16)	0.28008 (9)	0.62057 (11)	0.0181 (3)
C7	0.46282 (16)	0.22884 (9)	0.69374 (11)	0.0173 (3)
H7	0.5066	0.1884	0.6557	0.021*
C8	0.57885 (16)	0.27978 (9)	0.75365 (11)	0.0182 (3)
C9	0.70525 (17)	0.29325 (9)	0.71557 (11)	0.0195 (3)
C10	0.82323 (16)	0.34044 (9)	0.77743 (12)	0.0212 (3)
H10A	0.8826	0.3637	0.7344	0.025*
H10B	0.8828	0.3034	0.8247	0.025*
C11	0.76993 (17)	0.40884 (9)	0.83440 (12)	0.0216 (3)
C12	0.67029 (16)	0.37278 (9)	0.89612 (11)	0.0204 (3)
H12A	0.7278	0.3468	0.9554	0.024*
H12B	0.6167	0.4175	0.9186	0.024*
C13	0.56744 (16)	0.31146 (9)	0.84253 (11)	0.0173 (3)
C14	0.69201 (19)	0.47206 (10)	0.76251 (13)	0.0298 (4)
H14A	0.7563	0.4945	0.7236	0.045*
H14B	0.6581	0.5156	0.7995	0.045*
H14C	0.6117	0.4465	0.7184	0.045*
C15	0.89404 (18)	0.44878 (10)	0.90356 (13)	0.0273 (4)
H15A	0.9575	0.4726	0.8649	0.041*
H15B	0.9452	0.4081	0.9487	0.041*
H15C	0.8592	0.4913	0.9415	0.041*
C16	0.43798 (17)	0.32332 (9)	0.97968 (11)	0.0204 (3)
H16A	0.5266	0.3500	1.0131	0.025*
H16B	0.4154	0.2808	1.0243	0.025*
C17	0.32055 (19)	0.38537 (10)	0.96141 (12)	0.0266 (4)
H17A	0.2323	0.3602	0.9249	0.032*
H17B	0.3039	0.4060	1.0249	0.032*
C18	0.38348 (16)	0.21533 (9)	0.85240 (11)	0.0169 (3)
C19	0.29342 (16)	0.17702 (9)	0.91636 (11)	0.0195 (3)
H19A	0.2381	0.2200	0.9405	0.023*
H19B	0.3559	0.1523	0.9745	0.023*
C20	0.19150 (17)	0.11202 (9)	0.86392 (11)	0.0203 (3)
C21	0.27110 (18)	0.05689 (9)	0.80557 (12)	0.0236 (4)
H21A	0.3488	0.0292	0.8514	0.028*
H21B	0.2063	0.0150	0.7708	0.028*
C22	0.33022 (16)	0.10522 (9)	0.73201 (11)	0.0193 (3)
C23	0.39203 (16)	0.18370 (9)	0.76380 (11)	0.0179 (3)
C24	0.13741 (18)	0.06237 (10)	0.94152 (13)	0.0259 (4)
H24A	0.0883	0.0981	0.9795	0.039*
H24B	0.2172	0.0365	0.9859	0.039*
H24C	0.0722	0.0207	0.9088	0.039*
C25	0.06713 (17)	0.15154 (10)	0.79316 (12)	0.0238 (4)
H25A	0.1023	0.1835	0.7439	0.036*
H25B	0.0162	0.1870	0.8303	0.036*
H25C	0.0033	0.1094	0.7600	0.036*
H1	0.5572 (17)	0.2508 (14)	0.5393 (12)	0.051 (7)*
H4	0.2939 (18)	0.4842 (11)	0.8949 (16)	0.053 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0232 (6)	0.0345 (7)	0.0163 (6)	−0.0009 (5)	0.0056 (5)	−0.0008 (5)
O2	0.0219 (6)	0.0323 (6)	0.0188 (6)	−0.0007 (5)	0.0074 (5)	−0.0029 (5)
O3	0.0310 (7)	0.0246 (6)	0.0225 (6)	−0.0054 (5)	0.0110 (5)	−0.0070 (5)
O4	0.0373 (8)	0.0282 (7)	0.0454 (8)	0.0109 (6)	0.0175 (6)	0.0102 (6)
N1	0.0183 (7)	0.0202 (6)	0.0141 (6)	0.0011 (5)	0.0040 (5)	−0.0022 (5)
C1	0.0210 (8)	0.0203 (8)	0.0181 (7)	−0.0056 (6)	0.0041 (6)	−0.0021 (6)
C2	0.0262 (9)	0.0266 (8)	0.0181 (8)	−0.0098 (7)	0.0009 (7)	0.0014 (7)
C3	0.0218 (8)	0.0229 (8)	0.0244 (8)	−0.0047 (7)	−0.0049 (7)	0.0027 (7)
C4	0.0208 (8)	0.0212 (8)	0.0261 (8)	−0.0010 (7)	0.0013 (7)	−0.0031 (7)
C5	0.0213 (8)	0.0196 (8)	0.0190 (8)	−0.0039 (6)	0.0034 (6)	−0.0027 (6)
C6	0.0191 (8)	0.0170 (7)	0.0170 (7)	−0.0059 (6)	0.0007 (6)	−0.0024 (6)
C7	0.0186 (8)	0.0193 (7)	0.0151 (7)	−0.0003 (6)	0.0057 (6)	−0.0021 (6)
C8	0.0184 (8)	0.0186 (7)	0.0174 (7)	0.0020 (6)	0.0036 (6)	0.0015 (6)
C9	0.0201 (8)	0.0203 (8)	0.0182 (8)	0.0035 (6)	0.0039 (6)	0.0024 (6)
C10	0.0187 (8)	0.0245 (8)	0.0204 (8)	−0.0006 (7)	0.0044 (6)	0.0013 (7)
C11	0.0209 (8)	0.0203 (8)	0.0230 (8)	−0.0012 (6)	0.0029 (7)	−0.0004 (7)
C12	0.0193 (8)	0.0219 (8)	0.0191 (8)	0.0024 (6)	0.0020 (6)	−0.0032 (6)
C13	0.0167 (8)	0.0174 (7)	0.0172 (7)	0.0039 (6)	0.0024 (6)	0.0012 (6)
C14	0.0313 (10)	0.0240 (8)	0.0322 (9)	0.0013 (7)	0.0021 (8)	0.0045 (7)
C15	0.0231 (9)	0.0280 (9)	0.0305 (9)	−0.0042 (7)	0.0048 (7)	−0.0041 (7)
C16	0.0243 (8)	0.0234 (8)	0.0144 (7)	0.0007 (7)	0.0058 (6)	−0.0040 (6)
C17	0.0338 (10)	0.0248 (8)	0.0244 (8)	0.0055 (7)	0.0132 (7)	−0.0010 (7)
C18	0.0154 (7)	0.0170 (7)	0.0179 (7)	0.0033 (6)	0.0026 (6)	0.0010 (6)
C19	0.0218 (8)	0.0223 (8)	0.0152 (7)	0.0017 (6)	0.0059 (6)	−0.0003 (6)
C20	0.0220 (8)	0.0204 (8)	0.0201 (8)	−0.0011 (6)	0.0080 (7)	0.0008 (6)
C21	0.0286 (9)	0.0186 (8)	0.0257 (8)	0.0004 (7)	0.0105 (7)	−0.0003 (7)
C22	0.0188 (8)	0.0201 (7)	0.0196 (7)	0.0026 (6)	0.0057 (6)	−0.0005 (6)
C23	0.0179 (8)	0.0185 (7)	0.0176 (7)	0.0025 (6)	0.0047 (6)	0.0004 (6)
C24	0.0299 (9)	0.0240 (8)	0.0268 (8)	−0.0012 (7)	0.0127 (7)	0.0031 (7)
C25	0.0208 (8)	0.0281 (8)	0.0230 (8)	−0.0031 (7)	0.0058 (7)	0.0000 (7)

Geometric parameters (Å, º) top

O1—C1	1.3690 (19)	C12—C13	1.504 (2)
O1—H1	0.841 (10)	C12—H12A	0.9900
O2—C9	1.2442 (18)	C12—H12B	0.9900
O3—C22	1.2349 (18)	C14—H14A	0.9800
O4—C17	1.411 (2)	C14—H14B	0.9800
O4—H4	0.852 (9)	C14—H14C	0.9800
N1—C13	1.3975 (19)	C15—H15A	0.9800
N1—C18	1.400 (2)	C15—H15B	0.9800
N1—C16	1.4785 (18)	C15—H15C	0.9800
C1—C2	1.388 (2)	C16—C17	1.514 (2)
C1—C6	1.401 (2)	C16—H16A	0.9900
C2—C3	1.384 (2)	C16—H16B	0.9900
C2—H2	0.9500	C17—H17A	0.9900
C3—C4	1.386 (2)	C17—H17B	0.9900
C3—H3	0.9500	C18—C23	1.355 (2)
C4—C5	1.384 (2)	C18—C19	1.510 (2)
C4—H4A	0.9500	C19—C20	1.535 (2)
C5—C6	1.393 (2)	C19—H19A	0.9900
C5—H5	0.9500	C19—H19B	0.9900
C6—C7	1.528 (2)	C20—C24	1.532 (2)
C7—C23	1.502 (2)	C20—C21	1.531 (2)
C7—C8	1.508 (2)	C20—C25	1.533 (2)
C7—H7	1.0000	C21—C22	1.502 (2)
C8—C13	1.366 (2)	C21—H21A	0.9900
C8—C9	1.451 (2)	C21—H21B	0.9900
C9—C10	1.497 (2)	C22—C23	1.457 (2)
C10—C11	1.530 (2)	C24—H24A	0.9800
C10—H10A	0.9900	C24—H24B	0.9800
C10—H10B	0.9900	C24—H24C	0.9800
C11—C15	1.524 (2)	C25—H25A	0.9800
C11—C14	1.530 (2)	C25—H25B	0.9800
C11—C12	1.540 (2)	C25—H25C	0.9800

C1—O1—H1	109.6 (16)	H14A—C14—H14C	109.5
C17—O4—H4	108.6 (15)	H14B—C14—H14C	109.5
C13—N1—C18	119.28 (12)	C11—C15—H15A	109.5
C13—N1—C16	120.69 (12)	C11—C15—H15B	109.5
C18—N1—C16	119.57 (12)	H15A—C15—H15B	109.5
O1—C1—C2	117.44 (14)	C11—C15—H15C	109.5
O1—C1—C6	121.71 (14)	H15A—C15—H15C	109.5
C2—C1—C6	120.83 (15)	H15B—C15—H15C	109.5
C3—C2—C1	120.06 (15)	N1—C16—C17	112.62 (13)
C3—C2—H2	120.0	N1—C16—H16A	109.1
C1—C2—H2	120.0	C17—C16—H16A	109.1
C2—C3—C4	120.13 (16)	N1—C16—H16B	109.1
C2—C3—H3	119.9	C17—C16—H16B	109.1
C4—C3—H3	119.9	H16A—C16—H16B	107.8
C5—C4—C3	119.46 (15)	O4—C17—C16	108.47 (13)
C5—C4—H4A	120.3	O4—C17—H17A	110.0
C3—C4—H4A	120.3	C16—C17—H17A	110.0
C4—C5—C6	121.74 (15)	O4—C17—H17B	110.0
C4—C5—H5	119.1	C16—C17—H17B	110.0
C6—C5—H5	119.1	H17A—C17—H17B	108.4
C5—C6—C1	117.76 (14)	C23—C18—N1	120.45 (13)
C5—C6—C7	121.80 (13)	C23—C18—C19	121.74 (14)
C1—C6—C7	120.43 (14)	N1—C18—C19	117.81 (12)
C23—C7—C8	108.04 (12)	C18—C19—C20	114.13 (12)
C23—C7—C6	112.22 (12)	C18—C19—H19A	108.7
C8—C7—C6	111.70 (12)	C20—C19—H19A	108.7
C23—C7—H7	108.2	C18—C19—H19B	108.7
C8—C7—H7	108.3	C20—C19—H19B	108.7
C6—C7—H7	108.2	H19A—C19—H19B	107.6
C13—C8—C9	120.37 (14)	C24—C20—C21	109.84 (13)
C13—C8—C7	121.27 (13)	C24—C20—C25	109.79 (13)
C9—C8—C7	118.35 (13)	C21—C20—C25	109.31 (13)
O2—C9—C8	121.33 (14)	C24—C20—C19	108.81 (13)
O2—C9—C10	120.38 (14)	C21—C20—C19	108.68 (13)
C8—C9—C10	118.27 (13)	C25—C20—C19	110.39 (13)
C9—C10—C11	112.33 (13)	C22—C21—C20	110.56 (13)
C9—C10—H10A	109.1	C22—C21—H21A	109.5
C11—C10—H10A	109.1	C20—C21—H21A	109.5
C9—C10—H10B	109.1	C22—C21—H21B	109.5
C11—C10—H10B	109.1	C20—C21—H21B	109.5
H10A—C10—H10B	107.9	H21A—C21—H21B	108.1
C15—C11—C14	109.44 (14)	O3—C22—C23	121.15 (14)
C15—C11—C10	109.70 (13)	O3—C22—C21	121.56 (14)
C14—C11—C10	109.92 (13)	C23—C22—C21	117.28 (13)
C15—C11—C12	108.79 (13)	C18—C23—C22	121.21 (13)
C14—C11—C12	110.17 (13)	C18—C23—C7	121.36 (14)
C10—C11—C12	108.80 (12)	C22—C23—C7	117.42 (13)
C13—C12—C11	114.45 (12)	C20—C24—H24A	109.5
C13—C12—H12A	108.6	C20—C24—H24B	109.5
C11—C12—H12A	108.6	H24A—C24—H24B	109.5
C13—C12—H12B	108.6	C20—C24—H24C	109.5
C11—C12—H12B	108.6	H24A—C24—H24C	109.5
H12A—C12—H12B	107.6	H24B—C24—H24C	109.5
C8—C13—N1	119.79 (14)	C20—C25—H25A	109.5
C8—C13—C12	122.23 (13)	C20—C25—H25B	109.5
N1—C13—C12	117.95 (13)	H25A—C25—H25B	109.5
C11—C14—H14A	109.5	C20—C25—H25C	109.5
C11—C14—H14B	109.5	H25A—C25—H25C	109.5
H14A—C14—H14B	109.5	H25B—C25—H25C	109.5
C11—C14—H14C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84 (1)	1.84 (1)	2.659 (2)	166 (2)
O4—H4···O3ⁱ	0.85 (1)	1.98 (1)	2.818 (2)	166 (2)

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

Experimental details

Crystal data
Chemical formula	C₂₅H₃₁NO₄
M_r	409.51
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.7037 (2), 16.5123 (3), 13.8847 (3)
β (°)	102.132 (3)
V (Å³)	2175.06 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.979, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	19082, 4915, 3770
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.123, 1.03
No. of reflections	4915
No. of parameters	279
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.26

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84 (1)	1.84 (1)	2.659 (2)	166 (2)
O4—H4···O3ⁱ	0.85 (1)	1.98 (1)	2.818 (2)	166 (2)

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

Acknowledgements

We thank Manchester Metropolitan University, Baku State University and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Jang, H., Li, T., Tu, S. & Zou, X. (2005). Acta Cryst. E61, o2296–o2298. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 3| March 2011| Page o744

doi:10.1107/S1600536811006969

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

10-(2-Hy­dr­oxy­eth­yl)-9-(2-hy­dr­oxy­phen­yl)-3,3,6,6-tetra­methyl-1,2,3,4,5,6,7,8,9,10-deca­hydro­acridine-1,8-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

10-(2-Hydroxyethyl)-9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione