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

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

doi:10.1107/S1600536811013481

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1146

doi:10.1107/S1600536811013481

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

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

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

(Received 10 April 2011; accepted 11 April 2011; online 16 April 2011)

The dihydropyridine ring in the title compound, C₂₆H₃₂BrNO₄, adopts an envelope conformation with the methine C atom representing the flap. The cyclohexenone rings also adopt envelope conformations. The phenolic hydroxy group forms an intramolecular hydrogen bond to one of the two keto O atoms. Intermolecular weak C—H⋯O hydrogen bonding is present in the crystal structure. The hydroxypropyl group is disordered over two sets of sites with an occupancy ratio of 0.636 (6):0.364 (6).

Related literature

For a related structure, see: Abdelhamid et al. (2011 ).

Experimental

Crystal data

C₂₆H₃₂BrNO₄
M_r = 502.44
Monoclinic, P 2₁ /n
a = 10.6685 (4) Å
b = 16.8190 (5) Å
c = 14.1260 (5) Å
β = 106.303 (3)°
V = 2432.76 (14) Å³
Z = 4
Mo Kα radiation
μ = 1.72 mm⁻¹
T = 100 K
0.20 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.725, T_max = 0.919
11939 measured reflections
5402 independent reflections
3939 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.135
S = 1.03
5402 reflections
302 parameters
24 restraints
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.66 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	1.78	2.621 (4)	176
C10—H10A⋯O1ⁱ	0.99	2.54	3.417 (5)	147
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536811013481/xu5192sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013481/xu5192Isup2.hkl

checkCIF report

Comment top

In an earlier study, we reported 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, which was synthesized by the reaction of dimedone, salicyladehyde and 2-aminoethanol (Abdelhamid et al., 2011). In the present study, we replaced 2-aminoethanol by 1-amino-2-propanol and also used a bromine-subsituted salicyladehyde to form the title analog (Scheme I). The dihydropyridine ring in the C₂₆H₃₂BrNO₄ 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 (Fig. 1).

Related literature top

For a related structure, see: Abdelhamid et al. (2011).

Experimental top

5-Bromo-2-hydroxybenzaldehyde (10 mmol), 1-amino-2-propanol (10 mol) and 20 dimedone (20 mmol) were heated in pyridine (50 ml) for 5 h. The solid that was isolated from the cool solution was collected and recrystallized from ethano; m.p. 508 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 C₂₆H₃₂BrNO₄ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.

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

Crystal data top

C₂₆H₃₂BrNO₄	F(000) = 1048
M_r = 502.44	D_x = 1.372 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3308 reflections
a = 10.6685 (4) Å	θ = 2.3–29.4°
b = 16.8190 (5) Å	µ = 1.72 mm⁻¹
c = 14.1260 (5) Å	T = 100 K
β = 106.303 (3)°	Prism, colorless
V = 2432.76 (14) Å³	0.20 × 0.10 × 0.05 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5402 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3939 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.045
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.3°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −21→19
T_min = 0.725, T_max = 0.919	l = −13→17
11939 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0549P)² + 1.4767P] where P = (F_o² + 2F_c²)/3
5402 reflections	(Δ/σ)_max = 0.001
302 parameters	Δρ_max = 0.76 e Å⁻³
24 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

C₂₆H₃₂BrNO₄	V = 2432.76 (14) Å³
M_r = 502.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.6685 (4) Å	µ = 1.72 mm⁻¹
b = 16.8190 (5) Å	T = 100 K
c = 14.1260 (5) Å	0.20 × 0.10 × 0.05 mm
β = 106.303 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5402 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3939 reflections with I > 2σ(I)
T_min = 0.725, T_max = 0.919	R_int = 0.045
11939 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	24 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.03	Δρ_max = 0.76 e Å⁻³
5402 reflections	Δρ_min = −0.66 e Å⁻³
302 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	1.00011 (3)	0.07288 (2)	0.84090 (3)	0.02822 (14)
O1	0.6038 (2)	0.22434 (18)	1.01434 (16)	0.0322 (6)
H1	0.5337	0.2333	0.9706	0.039*
O2	0.3796 (2)	0.25478 (16)	0.88504 (17)	0.0306 (6)
O3	0.7557 (3)	0.41222 (15)	0.86062 (17)	0.0284 (6)
O4	0.6148 (10)	0.0597 (4)	0.6070 (6)	0.0224 (9)	0.636 (6)
H4	0.6748	0.0648	0.6598	0.027*	0.636 (6)
O4'	0.6669 (7)	0.0829 (4)	0.4503 (4)	0.0224 (9)	0.364
H4'	0.7173	0.0435	0.4608	0.027*	0.364 (6)
N1	0.5582 (3)	0.22319 (18)	0.61661 (19)	0.0209 (6)
C1	0.6924 (4)	0.1925 (2)	0.9722 (2)	0.0253 (8)
C2	0.7829 (4)	0.1395 (2)	1.0291 (2)	0.0291 (9)
H2	0.7803	0.1273	1.0942	0.035*
C3	0.8759 (4)	0.1044 (2)	0.9923 (2)	0.0274 (8)
H3	0.9380	0.0686	1.0315	0.033*
C4	0.8772 (3)	0.1223 (2)	0.8975 (2)	0.0231 (8)
C5	0.7896 (3)	0.1759 (2)	0.8406 (2)	0.0206 (7)
H5	0.7928	0.1873	0.7754	0.025*
C6	0.6975 (3)	0.2134 (2)	0.8771 (2)	0.0195 (7)
C7	0.6024 (3)	0.2741 (2)	0.8146 (2)	0.0218 (7)
H7	0.5812	0.3146	0.8595	0.026*
C8	0.4774 (3)	0.2344 (2)	0.7571 (2)	0.0214 (7)
C9	0.3703 (3)	0.2291 (2)	0.8002 (2)	0.0245 (8)
C10	0.2455 (4)	0.1933 (2)	0.7402 (3)	0.0316 (9)
H10A	0.1952	0.2335	0.6935	0.038*
H10B	0.1923	0.1768	0.7841	0.038*
C11	0.2724 (4)	0.1208 (2)	0.6826 (3)	0.0320 (9)
C12	0.3568 (3)	0.1482 (2)	0.6168 (2)	0.0260 (8)
H12A	0.3945	0.1007	0.5937	0.031*
H12B	0.2999	0.1750	0.5580	0.031*
C13	0.4664 (3)	0.2038 (2)	0.6662 (2)	0.0213 (8)
C14	0.3435 (4)	0.0568 (2)	0.7541 (3)	0.0392 (10)
H14A	0.3604	0.0108	0.7169	0.059*
H14B	0.2893	0.0404	0.7964	0.059*
H14C	0.4266	0.0780	0.7951	0.059*
C15	0.1428 (4)	0.0876 (3)	0.6174 (3)	0.0461 (12)
H15A	0.1603	0.0414	0.5808	0.069*
H15B	0.0980	0.1286	0.5709	0.069*
H15C	0.0876	0.0715	0.6590	0.069*
C16	0.5558 (3)	0.1821 (2)	0.5232 (2)	0.0253 (8)
H16A	0.5847	0.2201	0.4799	0.030*	0.636 (6)
H16B	0.4645	0.1671	0.4893	0.030*	0.636 (6)
H16C	0.5683	0.2211	0.4740	0.030*	0.364 (6)
H16D	0.4706	0.1554	0.4958	0.030*	0.364 (6)
C17	0.6394 (8)	0.1092 (5)	0.5351 (6)	0.035 (2)	0.636 (6)
H17	0.6079	0.0794	0.4715	0.042*	0.636 (6)
C17'	0.6674 (17)	0.1202 (11)	0.5460 (9)	0.035 (2)	0.364
H17'	0.7542	0.1415	0.5846	0.042*	0.364 (6)
C18	0.7835 (8)	0.1139 (5)	0.5556 (6)	0.064 (3)	0.636 (6)
H18A	0.8061	0.1579	0.5180	0.096*	0.636 (6)
H18B	0.8165	0.0639	0.5361	0.096*	0.636 (6)
H18C	0.8230	0.1229	0.6262	0.096*	0.636 (6)
C18'	0.613 (4)	0.0541 (18)	0.598 (2)	0.064 (3)	0.364
H18D	0.6726	0.0085	0.6100	0.096*	0.364 (6)
H18E	0.5270	0.0377	0.5569	0.096*	0.364 (6)
H18F	0.6050	0.0740	0.6615	0.096*	0.364 (6)
C19	0.6444 (3)	0.2861 (2)	0.6502 (2)	0.0207 (7)
C20	0.7162 (3)	0.3212 (2)	0.5820 (2)	0.0221 (7)
H20A	0.6538	0.3531	0.5310	0.027*
H20B	0.7475	0.2772	0.5480	0.027*
C21	0.8325 (3)	0.3738 (2)	0.6323 (2)	0.0208 (7)
C22	0.7910 (4)	0.4311 (2)	0.7019 (2)	0.0241 (8)
H22A	0.8672	0.4633	0.7376	0.029*
H22B	0.7236	0.4677	0.6628	0.029*
C23	0.7371 (3)	0.3877 (2)	0.7761 (2)	0.0222 (8)
C24	0.6607 (3)	0.3159 (2)	0.7426 (2)	0.0208 (7)
C25	0.8732 (4)	0.4213 (2)	0.5529 (3)	0.0273 (8)
H25A	0.9004	0.3846	0.5085	0.041*
H25B	0.9460	0.4566	0.5845	0.041*
H25C	0.7991	0.4531	0.5150	0.041*
C26	0.9486 (3)	0.3234 (2)	0.6901 (2)	0.0258 (8)
H26A	0.9746	0.2869	0.6449	0.039*
H26B	0.9233	0.2928	0.7409	0.039*
H26C	1.0220	0.3584	0.7214	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0228 (2)	0.0251 (2)	0.0361 (2)	0.00032 (17)	0.00727 (15)	0.00592 (15)
O1	0.0261 (15)	0.0483 (19)	0.0246 (13)	−0.0083 (14)	0.0109 (10)	−0.0029 (12)
O2	0.0265 (15)	0.0350 (17)	0.0343 (14)	−0.0001 (13)	0.0150 (11)	0.0000 (12)
O3	0.0345 (15)	0.0256 (15)	0.0268 (13)	−0.0060 (12)	0.0116 (11)	−0.0040 (10)
O4	0.036 (2)	0.017 (2)	0.021 (2)	0.0144 (17)	0.0188 (16)	0.0029 (14)
O4'	0.036 (2)	0.017 (2)	0.021 (2)	0.0144 (17)	0.0188 (16)	0.0029 (14)
N1	0.0162 (15)	0.0231 (17)	0.0220 (14)	−0.0008 (13)	0.0029 (11)	0.0031 (12)
C1	0.023 (2)	0.032 (2)	0.0206 (17)	−0.0126 (17)	0.0060 (14)	−0.0035 (15)
C2	0.036 (2)	0.032 (2)	0.0185 (17)	−0.0117 (19)	0.0072 (15)	0.0053 (15)
C3	0.027 (2)	0.025 (2)	0.0243 (18)	−0.0072 (17)	−0.0018 (14)	0.0073 (15)
C4	0.0187 (19)	0.022 (2)	0.0266 (18)	−0.0048 (16)	0.0040 (14)	0.0021 (14)
C5	0.0211 (18)	0.0206 (19)	0.0192 (16)	−0.0067 (15)	0.0039 (13)	−0.0003 (13)
C6	0.0202 (19)	0.0179 (19)	0.0197 (16)	−0.0072 (15)	0.0047 (13)	−0.0003 (13)
C7	0.0217 (19)	0.0215 (19)	0.0230 (17)	−0.0027 (16)	0.0076 (13)	0.0000 (14)
C8	0.0202 (18)	0.0174 (19)	0.0258 (18)	0.0021 (15)	0.0052 (13)	0.0057 (14)
C9	0.0205 (19)	0.022 (2)	0.0307 (19)	0.0015 (16)	0.0070 (14)	0.0067 (15)
C10	0.020 (2)	0.042 (3)	0.034 (2)	−0.0015 (18)	0.0095 (15)	0.0067 (17)
C11	0.024 (2)	0.034 (2)	0.035 (2)	−0.0081 (18)	0.0030 (15)	0.0056 (17)
C12	0.0193 (19)	0.027 (2)	0.0292 (19)	−0.0010 (17)	0.0025 (14)	0.0030 (15)
C13	0.0149 (17)	0.024 (2)	0.0242 (18)	0.0024 (15)	0.0033 (13)	0.0066 (14)
C14	0.044 (3)	0.030 (2)	0.041 (2)	−0.011 (2)	0.0076 (18)	0.0081 (17)
C15	0.033 (2)	0.059 (3)	0.042 (2)	−0.023 (2)	0.0049 (18)	0.006 (2)
C16	0.0224 (19)	0.029 (2)	0.0244 (18)	0.0014 (17)	0.0072 (14)	0.0023 (15)
C17	0.031 (5)	0.042 (4)	0.038 (3)	0.010 (4)	0.020 (3)	0.016 (2)
C17'	0.031 (5)	0.042 (4)	0.038 (3)	0.010 (4)	0.020 (3)	0.016 (2)
C18	0.066 (5)	0.069 (5)	0.058 (4)	0.001 (4)	0.021 (4)	0.013 (4)
C18'	0.066 (5)	0.069 (5)	0.058 (4)	0.001 (4)	0.021 (4)	0.013 (4)
C19	0.0142 (17)	0.0214 (19)	0.0256 (17)	0.0034 (15)	0.0041 (13)	0.0065 (14)
C20	0.0202 (18)	0.023 (2)	0.0253 (17)	0.0049 (16)	0.0091 (13)	0.0072 (14)
C21	0.0193 (18)	0.0197 (19)	0.0252 (17)	0.0019 (15)	0.0092 (13)	0.0040 (14)
C22	0.028 (2)	0.0162 (19)	0.0308 (19)	0.0032 (16)	0.0136 (15)	0.0049 (14)
C23	0.0170 (18)	0.020 (2)	0.0299 (19)	0.0031 (15)	0.0075 (14)	0.0055 (14)
C24	0.0155 (17)	0.0199 (19)	0.0270 (18)	−0.0001 (15)	0.0061 (13)	0.0053 (14)
C25	0.030 (2)	0.024 (2)	0.0312 (19)	0.0009 (17)	0.0142 (15)	0.0045 (15)
C26	0.0206 (19)	0.027 (2)	0.0304 (19)	0.0010 (17)	0.0088 (14)	0.0023 (15)

Geometric parameters (Å, º) top

Br1—C4	1.908 (4)	C14—H14C	0.9800
O1—C1	1.360 (4)	C15—H15A	0.9800
O1—H1	0.8400	C15—H15B	0.9800
O2—C9	1.251 (4)	C15—H15C	0.9800
O3—C23	1.226 (4)	C16—C17	1.499 (7)
O4—C17	1.394 (7)	C16—C17'	1.547 (9)
O4—H4	0.8400	C16—H16A	0.9900
O4'—C17'	1.488 (10)	C16—H16B	0.9900
O4'—H4'	0.8400	C16—H16C	0.9900
N1—C13	1.393 (4)	C16—H16D	0.9900
N1—C19	1.394 (4)	C17—C18	1.484 (8)
N1—C16	1.483 (4)	C17—H17	1.0000
C1—C2	1.391 (5)	C17'—C18'	1.535 (10)
C1—C6	1.405 (5)	C17'—H17'	1.0000
C2—C3	1.376 (5)	C18—H18A	0.9800
C2—H2	0.9500	C18—H18B	0.9800
C3—C4	1.376 (5)	C18—H18C	0.9800
C3—H3	0.9500	C18'—H18D	0.9800
C4—C5	1.382 (5)	C18'—H18E	0.9800
C5—C6	1.383 (5)	C18'—H18F	0.9800
C5—H5	0.9500	C19—C24	1.364 (5)
C6—C7	1.532 (5)	C19—C20	1.509 (4)
C7—C24	1.507 (4)	C20—C21	1.526 (5)
C7—C8	1.509 (5)	C20—H20A	0.9900
C7—H7	1.0000	C20—H20B	0.9900
C8—C13	1.357 (5)	C21—C22	1.529 (5)
C8—C9	1.440 (5)	C21—C26	1.533 (5)
C9—C10	1.490 (5)	C21—C25	1.536 (5)
C10—C11	1.538 (6)	C22—C23	1.516 (5)
C10—H10A	0.9900	C22—H22A	0.9900
C10—H10B	0.9900	C22—H22B	0.9900
C11—C14	1.525 (5)	C23—C24	1.459 (5)
C11—C12	1.535 (5)	C25—H25A	0.9800
C11—C15	1.535 (5)	C25—H25B	0.9800
C12—C13	1.507 (5)	C25—H25C	0.9800
C12—H12A	0.9900	C26—H26A	0.9800
C12—H12B	0.9900	C26—H26B	0.9800
C14—H14A	0.9800	C26—H26C	0.9800
C14—H14B	0.9800

C1—O1—H1	109.5	C17'—C16—H16A	102.0
C17'—O4'—H4'	109.5	N1—C16—H16B	108.6
C13—N1—C19	119.7 (3)	C17—C16—H16B	108.6
C13—N1—C16	119.9 (3)	H16A—C16—H16B	107.5
C19—N1—C16	120.1 (3)	N1—C16—H16C	110.1
O1—C1—C2	117.0 (3)	C17—C16—H16C	115.3
O1—C1—C6	122.5 (3)	C17'—C16—H16C	110.1
C2—C1—C6	120.4 (3)	N1—C16—H16D	110.1
C3—C2—C1	120.9 (3)	C17'—C16—H16D	110.1
C3—C2—H2	119.5	H16C—C16—H16D	108.4
C1—C2—H2	119.5	O4—C17—C18	106.6 (7)
C2—C3—C4	118.6 (3)	O4—C17—C16	110.0 (6)
C2—C3—H3	120.7	C18—C17—C16	122.0 (8)
C4—C3—H3	120.7	O4—C17—H17	105.7
C3—C4—C5	121.3 (3)	C18—C17—H17	105.7
C3—C4—Br1	120.5 (3)	C16—C17—H17	105.7
C5—C4—Br1	118.2 (2)	O4'—C17'—C18'	103.1 (17)
C6—C5—C4	121.0 (3)	O4'—C17'—C16	106.7 (8)
C6—C5—H5	119.5	C18'—C17'—C16	102 (2)
C4—C5—H5	119.5	O4'—C17'—H17'	114.4
C5—C6—C1	117.7 (3)	C18'—C17'—H17'	114.4
C5—C6—C7	120.9 (3)	C16—C17'—H17'	114.4
C1—C6—C7	121.4 (3)	C17—C18—H18A	109.5
C24—C7—C8	108.3 (3)	C17—C18—H18B	109.5
C24—C7—C6	111.6 (3)	H18A—C18—H18B	109.5
C8—C7—C6	110.9 (3)	C17—C18—H18C	109.5
C24—C7—H7	108.7	H18A—C18—H18C	109.5
C8—C7—H7	108.7	H18B—C18—H18C	109.5
C6—C7—H7	108.7	C17'—C18'—H18D	109.5
C13—C8—C9	120.6 (3)	C17'—C18'—H18E	109.5
C13—C8—C7	120.3 (3)	H18D—C18'—H18E	109.5
C9—C8—C7	119.0 (3)	C17'—C18'—H18F	109.5
O2—C9—C8	121.7 (3)	H18D—C18'—H18F	109.5
O2—C9—C10	120.1 (3)	H18E—C18'—H18F	109.5
C8—C9—C10	118.2 (3)	C24—C19—N1	120.0 (3)
C9—C10—C11	110.6 (3)	C24—C19—C20	121.1 (3)
C9—C10—H10A	109.5	N1—C19—C20	119.0 (3)
C11—C10—H10A	109.5	C19—C20—C21	115.0 (3)
C9—C10—H10B	109.5	C19—C20—H20A	108.5
C11—C10—H10B	109.5	C21—C20—H20A	108.5
H10A—C10—H10B	108.1	C19—C20—H20B	108.5
C14—C11—C12	110.2 (3)	C21—C20—H20B	108.5
C14—C11—C15	109.7 (3)	H20A—C20—H20B	107.5
C12—C11—C15	109.2 (3)	C20—C21—C22	108.7 (3)
C14—C11—C10	110.0 (3)	C20—C21—C26	111.0 (3)
C12—C11—C10	108.2 (3)	C22—C21—C26	110.0 (3)
C15—C11—C10	109.6 (4)	C20—C21—C25	108.8 (3)
C13—C12—C11	114.6 (3)	C22—C21—C25	109.5 (3)
C13—C12—H12A	108.6	C26—C21—C25	109.0 (3)
C11—C12—H12A	108.6	C23—C22—C21	112.1 (3)
C13—C12—H12B	108.6	C23—C22—H22A	109.2
C11—C12—H12B	108.6	C21—C22—H22A	109.2
H12A—C12—H12B	107.6	C23—C22—H22B	109.2
C8—C13—N1	120.0 (3)	C21—C22—H22B	109.2
C8—C13—C12	121.5 (3)	H22A—C22—H22B	107.9
N1—C13—C12	118.5 (3)	O3—C23—C24	121.2 (3)
C11—C14—H14A	109.5	O3—C23—C22	121.5 (3)
C11—C14—H14B	109.5	C24—C23—C22	117.4 (3)
H14A—C14—H14B	109.5	C19—C24—C23	121.6 (3)
C11—C14—H14C	109.5	C19—C24—C7	120.6 (3)
H14A—C14—H14C	109.5	C23—C24—C7	117.8 (3)
H14B—C14—H14C	109.5	C21—C25—H25A	109.5
C11—C15—H15A	109.5	C21—C25—H25B	109.5
C11—C15—H15B	109.5	H25A—C25—H25B	109.5
H15A—C15—H15B	109.5	C21—C25—H25C	109.5
C11—C15—H15C	109.5	H25A—C25—H25C	109.5
H15A—C15—H15C	109.5	H25B—C25—H25C	109.5
H15B—C15—H15C	109.5	C21—C26—H26A	109.5
N1—C16—C17	114.8 (4)	C21—C26—H26B	109.5
N1—C16—C17'	107.9 (5)	H26A—C26—H26B	109.5
C17—C16—C17'	13.0 (11)	C21—C26—H26C	109.5
N1—C16—H16A	108.6	H26A—C26—H26C	109.5
C17—C16—H16A	108.6	H26B—C26—H26C	109.5

O1—C1—C2—C3	180.0 (3)	C11—C12—C13—C8	−8.0 (5)
C6—C1—C2—C3	−2.3 (6)	C11—C12—C13—N1	171.6 (3)
C1—C2—C3—C4	−0.5 (6)	C13—N1—C16—C17	−91.6 (6)
C2—C3—C4—C5	1.8 (5)	C19—N1—C16—C17	94.3 (6)
C2—C3—C4—Br1	−177.9 (3)	C13—N1—C16—C17'	−103.5 (10)
C3—C4—C5—C6	−0.1 (5)	C19—N1—C16—C17'	82.4 (10)
Br1—C4—C5—C6	179.5 (3)	N1—C16—C17—O4	49.4 (8)
C4—C5—C6—C1	−2.6 (5)	C17'—C16—C17—O4	110 (4)
C4—C5—C6—C7	178.7 (3)	N1—C16—C17—C18	−76.5 (8)
O1—C1—C6—C5	−178.6 (3)	C17'—C16—C17—C18	−16 (3)
C2—C1—C6—C5	3.8 (5)	N1—C16—C17'—O4'	−177.2 (10)
O1—C1—C6—C7	0.1 (5)	C17—C16—C17'—O4'	59 (3)
C2—C1—C6—C7	−177.6 (3)	N1—C16—C17'—C18'	74.8 (16)
C5—C6—C7—C24	−28.8 (4)	C17—C16—C17'—C18'	−49 (4)
C1—C6—C7—C24	152.6 (3)	C13—N1—C19—C24	15.8 (5)
C5—C6—C7—C8	92.0 (4)	C16—N1—C19—C24	−170.1 (3)
C1—C6—C7—C8	−86.6 (4)	C13—N1—C19—C20	−163.1 (3)
C24—C7—C8—C13	34.3 (4)	C16—N1—C19—C20	11.1 (4)
C6—C7—C8—C13	−88.5 (4)	C24—C19—C20—C21	16.5 (5)
C24—C7—C8—C9	−146.0 (3)	N1—C19—C20—C21	−164.7 (3)
C6—C7—C8—C9	91.2 (4)	C19—C20—C21—C22	−46.6 (4)
C13—C8—C9—O2	177.8 (3)	C19—C20—C21—C26	74.4 (4)
C7—C8—C9—O2	−1.9 (5)	C19—C20—C21—C25	−165.8 (3)
C13—C8—C9—C10	−3.3 (5)	C20—C21—C22—C23	55.7 (4)
C7—C8—C9—C10	177.0 (3)	C26—C21—C22—C23	−65.9 (4)
O2—C9—C10—C11	−140.9 (3)	C25—C21—C22—C23	174.4 (3)
C8—C9—C10—C11	40.3 (4)	C21—C22—C23—O3	144.8 (3)
C9—C10—C11—C14	62.2 (4)	C21—C22—C23—C24	−35.9 (4)
C9—C10—C11—C12	−58.2 (4)	N1—C19—C24—C23	−172.3 (3)
C9—C10—C11—C15	−177.2 (3)	C20—C19—C24—C23	6.5 (5)
C14—C11—C12—C13	−77.2 (4)	N1—C19—C24—C7	9.1 (5)
C15—C11—C12—C13	162.3 (3)	C20—C19—C24—C7	−172.1 (3)
C10—C11—C12—C13	43.1 (4)	O3—C23—C24—C19	−177.0 (3)
C9—C8—C13—N1	166.7 (3)	C22—C23—C24—C19	3.7 (5)
C7—C8—C13—N1	−13.6 (5)	O3—C23—C24—C7	1.6 (5)
C9—C8—C13—C12	−13.7 (5)	C22—C23—C24—C7	−177.7 (3)
C7—C8—C13—C12	165.9 (3)	C8—C7—C24—C19	−31.9 (4)
C19—N1—C13—C8	−13.5 (5)	C6—C7—C24—C19	90.4 (4)
C16—N1—C13—C8	172.4 (3)	C8—C7—C24—C23	149.4 (3)
C19—N1—C13—C12	166.9 (3)	C6—C7—C24—C23	−88.2 (4)
C16—N1—C13—C12	−7.2 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84	1.78	2.621 (4)	176
C10—H10A···O1ⁱ	0.99	2.54	3.417 (5)	147

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

Experimental details

Crystal data
Chemical formula	C₂₆H₃₂BrNO₄
M_r	502.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.6685 (4), 16.8190 (5), 14.1260 (5)
β (°)	106.303 (3)
V (Å³)	2432.76 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.72
Crystal size (mm)	0.20 × 0.10 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.725, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	11939, 5402, 3939
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.135, 1.03
No. of reflections	5402
No. of parameters	302
No. of restraints	24
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.66

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	1.78	2.621 (4)	176
C10—H10A···O1ⁱ	0.99	2.54	3.417 (5)	147

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

Acknowledgements

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

References

Abdelhamid, A. A., Mohamed, S. K., Khalilov, A. N., Gurbanov, A. V. & Ng, S. W. (2011). Acta Cryst. E67, o744. Web of Science CSD CrossRef IUCr Journals Google Scholar
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS 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 5| May 2011| Page o1146

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

9-(5-Bromo-2-hy­dr­oxy­phen­yl)-10-(2-hy­dr­oxy­prop­yl)-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

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