2-[6,8-Dibromo-3-(4-hydroxy­cyclo­hexyl)-1,2,3,4-tetra­hydro­quinazolin-2-yl]-6-methoxy­phenol

Wang, Z.-G.; Wang, R.; Zhang, Y.; Zhi, F.; Yang, Y.-L.

doi:10.1107/S1600536809005182

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o550

doi:10.1107/S1600536809005182

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2-[6,8-Dibromo-3-(4-hydroxycyclohexyl)-1,2,3,4-tetrahydroquinazolin-2-yl]-6-methoxyphenol

Zhi-Gang Wang,^a Rong Wang,^b Yi Zhang,^c Feng Zhi ^b ^* and Yi-Lin Yang ^c ^*

^aRespiratory Department, Third Affiliated Hospital of Soochow University, Changzhou 213003, People's Republic of China, ^bModern Medical Research Center, Third Affiliated Hospital of Soochow University, Changzhou 213003, People's Republic of China, and ^cDepartment of Neurosurgery, Third Affiliated Hospital of Soochow University, Changzhou 213003, People's Republic of China
^*Correspondence e-mail: wangzhigang_cz@163.com, yilinyang09@126.com

(Received 12 February 2009; accepted 13 February 2009; online 18 February 2009)

The title compound, C₂₁H₂₄Br₂N₂O₃, was synthesized by the condensation reaction of 3-methoxysalicylaldehyde with 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol in a methanol solution. The dihedral angle between the two benzene rings is 76.4 (3)°. The cyclohexyl ring adopts a chair configuration. There is an intramolecular O—H⋯N hydrogen bond which affects the solid state conformation of the molecule. The crystal structure is stabilized by intermolecular O—H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For details of the pharmaceutical uses of the closely related compound ambroxol, systematic name 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol, see: Felix et al. (2008 ); Gaida et al. (2005 ); Lee et al. (2004 ). For bond length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₂₄Br₂N₂O₃
M_r = 512.24
Triclinic, $[P \overline 1]$
a = 8.695 (2) Å
b = 11.124 (3) Å
c = 12.090 (2) Å
α = 73.870 (3)°
β = 78.226 (3)°
γ = 67.031 (2)°
V = 1028.2 (4) Å³
Z = 2
Mo Kα radiation
μ = 3.97 mm⁻¹
T = 298 K
0.30 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.382, T_max = 0.382 (expected range = 0.304–0.304)
8514 measured reflections
4305 independent reflections
3035 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.096
S = 1.02
4305 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.82	1.89	2.614 (3)	147
O1—H1⋯O3ⁱ	0.82	2.41	3.048 (4)	135
O1—H1⋯O2ⁱ	0.82	2.13	2.897 (4)	155
Symmetry code: (i) -x+1, -y+2, -z.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005182/sj2575sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809005182/sj2575Isup2.hkl

checkCIF report

Comment top

Ambroxol, 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol, is an expectorant agent which leads to bronchial secretion due to its mucolytic properties (Felix et al., 2008; Gaida et al., 2005; Lee et al., 2004). In this paper, the crystal structure of the new title compound, (I), derived from the condensation reaction of 3-methoxysalicylaldehyde with 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol in a methanol solution, is reported.

In (I), Fig. 1, the dihedral angle between the two benzene rings is 76.4 (3)°. The cyclohexyl ring adopts a chair configuration. All the bond lengths are within normal ranges (Allen et al., 1987). There is an intramolecular O2—H2···N2 hydrogen bond which affects the solid state conformation of the molecule. The crystal structure is stabilized by intermolecular O—H···O hydrogen bonds (Table 1), forming chains running along the b axis (Fig. 2).

Related literature top

For details of the pharmaceutical uses of the closely related compound ambroxol, systematic name 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol, see: Felix et al. (2008); Gaida et al. (2005); Lee et al. (2004). For bond length data, see: Allen et al. (1987).

Experimental top

3-Methoxysalicylaldehyde (1.0 mol, 152.1 mg) and 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol (1.0 mmol, 378.1 mg) were dissolved in a methanol solution (10 ml). The mixture was stirred at room temperature to give a clear colorless solution. Crystals of the title compound were formed by gradual evaporation of the solvent for a week at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I) at the 30% probability level. The intramolecular O–H···N hydrogen bond is shown as a dashed line.
	Fig. 2. Molecular packing of (I), viewed along the a axis. Intermolecular hydrogen bonds are shown as dashed lines.

(I) top

Crystal data top

C₂₁H₂₄Br₂N₂O₃	Z = 2
M_r = 512.24	F(000) = 516
Triclinic, P1	D_x = 1.655 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.695 (2) Å	Cell parameters from 2079 reflections
b = 11.124 (3) Å	θ = 2.3–24.6°
c = 12.090 (2) Å	µ = 3.97 mm⁻¹
α = 73.870 (3)°	T = 298 K
β = 78.226 (3)°	Block, colorless
γ = 67.031 (2)°	0.30 × 0.30 × 0.30 mm
V = 1028.2 (4) Å³

Data collection top

Bruker SMART CCD area detector diffractometer	4305 independent reflections
Radiation source: fine-focus sealed tube	3035 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.382, T_max = 0.382	k = −14→14
8514 measured reflections	l = −15→15

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0423P)² + 0.0168P] where P = (F_o² + 2F_c²)/3
4305 reflections	(Δ/σ)_max = 0.001
256 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₂₁H₂₄Br₂N₂O₃	γ = 67.031 (2)°
M_r = 512.24	V = 1028.2 (4) Å³
Triclinic, P1	Z = 2
a = 8.695 (2) Å	Mo Kα radiation
b = 11.124 (3) Å	µ = 3.97 mm⁻¹
c = 12.090 (2) Å	T = 298 K
α = 73.870 (3)°	0.30 × 0.30 × 0.30 mm
β = 78.226 (3)°

Data collection top

Bruker SMART CCD area detector diffractometer	4305 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3035 reflections with I > 2σ(I)
T_min = 0.382, T_max = 0.382	R_int = 0.032
8514 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.02	Δρ_max = 0.51 e Å⁻³
4305 reflections	Δρ_min = −0.41 e Å⁻³
256 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
Br1	1.17738 (5)	0.24247 (4)	0.32321 (4)	0.04726 (14)
Br2	1.28346 (5)	0.54977 (4)	0.58131 (3)	0.04402 (14)
O1	0.2331 (3)	0.9422 (3)	0.3052 (2)	0.0418 (7)
H1	0.1581	0.9883	0.2635	0.063*
O2	0.9413 (3)	0.8807 (3)	−0.1082 (2)	0.0430 (7)
H2	0.8961	0.8692	−0.0416	0.065*
O3	1.1435 (4)	0.9116 (3)	−0.2940 (2)	0.0510 (7)
N1	1.0518 (4)	0.5182 (3)	0.1542 (2)	0.0305 (7)
H1A	1.0527	0.4432	0.1469	0.037*
N2	0.9133 (3)	0.7617 (3)	0.1103 (2)	0.0249 (6)
C1	1.1053 (4)	0.6460 (3)	0.2638 (3)	0.0265 (8)
C2	1.1080 (4)	0.5243 (3)	0.2507 (3)	0.0263 (7)
C3	1.1674 (4)	0.4110 (3)	0.3381 (3)	0.0287 (8)
C4	1.2199 (4)	0.4172 (3)	0.4357 (3)	0.0317 (8)
H4	1.2586	0.3405	0.4931	0.038*
C5	1.2143 (4)	0.5386 (4)	0.4468 (3)	0.0302 (8)
C6	1.1591 (4)	0.6523 (3)	0.3620 (3)	0.0306 (8)
H6	1.1576	0.7334	0.3702	0.037*
C7	1.0414 (4)	0.7698 (3)	0.1692 (3)	0.0259 (7)
H7A	0.9929	0.8481	0.2027	0.031*
H7B	1.1349	0.7799	0.1128	0.031*
C8	0.7481 (4)	0.7705 (3)	0.1797 (3)	0.0269 (8)
H8	0.7560	0.6812	0.2263	0.032*
C9	0.6954 (4)	0.8659 (4)	0.2601 (3)	0.0377 (9)
H9A	0.6977	0.9525	0.2156	0.045*
H9B	0.7751	0.8324	0.3168	0.045*
C10	0.5210 (5)	0.8823 (4)	0.3222 (3)	0.0410 (10)
H10A	0.5213	0.7973	0.3722	0.049*
H10B	0.4908	0.9464	0.3705	0.049*
C11	0.3920 (4)	0.9293 (3)	0.2392 (3)	0.0322 (8)
H11	0.3880	1.0175	0.1918	0.039*
C12	0.4406 (4)	0.8330 (4)	0.1607 (3)	0.0414 (10)
H12A	0.3600	0.8662	0.1045	0.050*
H12B	0.4380	0.7468	0.2062	0.050*
C13	0.6155 (4)	0.8160 (4)	0.0976 (3)	0.0378 (9)
H13A	0.6452	0.7509	0.0504	0.045*
H13B	0.6143	0.9006	0.0463	0.045*
C14	0.9912 (4)	0.6381 (3)	0.0655 (3)	0.0255 (7)
H14	0.9030	0.6289	0.0329	0.031*
C15	1.1251 (4)	0.6565 (4)	−0.0355 (3)	0.0296 (8)
C16	1.0875 (4)	0.7752 (4)	−0.1185 (3)	0.0298 (8)
C17	1.1986 (5)	0.7917 (4)	−0.2178 (3)	0.0367 (9)
C18	1.3514 (5)	0.6900 (5)	−0.2301 (3)	0.0454 (11)
H18	1.4274	0.7007	−0.2951	0.055*
C19	1.3921 (5)	0.5718 (4)	−0.1457 (4)	0.0476 (11)
H19	1.4954	0.5038	−0.1541	0.057*
C20	1.2793 (4)	0.5554 (4)	−0.0496 (3)	0.0368 (9)
H20	1.3068	0.4759	0.0063	0.044*
C21	1.2282 (7)	0.9219 (5)	−0.4076 (3)	0.0797 (17)
H21A	1.3418	0.9132	−0.4048	0.120*
H21B	1.1715	1.0074	−0.4549	0.120*
H21C	1.2288	0.8521	−0.4400	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0577 (3)	0.0246 (2)	0.0575 (3)	−0.00942 (19)	−0.0134 (2)	−0.00831 (19)
Br2	0.0490 (3)	0.0547 (3)	0.0320 (2)	−0.0205 (2)	−0.01256 (18)	−0.00628 (18)
O1	0.0277 (14)	0.0408 (16)	0.0439 (16)	−0.0053 (13)	0.0025 (12)	−0.0038 (13)
O2	0.0370 (16)	0.0440 (16)	0.0302 (14)	−0.0040 (13)	0.0040 (12)	−0.0011 (12)
O3	0.0602 (19)	0.0570 (18)	0.0303 (15)	−0.0259 (16)	0.0092 (13)	−0.0038 (14)
N1	0.0405 (18)	0.0227 (15)	0.0294 (16)	−0.0106 (14)	−0.0055 (14)	−0.0073 (13)
N2	0.0216 (15)	0.0262 (15)	0.0263 (15)	−0.0077 (12)	−0.0019 (12)	−0.0068 (12)
C1	0.0208 (18)	0.0288 (19)	0.0291 (18)	−0.0088 (15)	−0.0031 (15)	−0.0048 (15)
C2	0.0186 (18)	0.0276 (18)	0.0313 (19)	−0.0066 (15)	0.0006 (14)	−0.0094 (15)
C3	0.028 (2)	0.0219 (18)	0.036 (2)	−0.0074 (16)	−0.0032 (16)	−0.0082 (16)
C4	0.027 (2)	0.029 (2)	0.031 (2)	−0.0038 (17)	−0.0074 (16)	−0.0005 (16)
C5	0.0239 (19)	0.039 (2)	0.0297 (19)	−0.0106 (17)	−0.0051 (15)	−0.0097 (17)
C6	0.0249 (19)	0.032 (2)	0.037 (2)	−0.0127 (16)	0.0005 (16)	−0.0098 (17)
C7	0.0232 (18)	0.0268 (18)	0.0297 (18)	−0.0096 (15)	−0.0042 (15)	−0.0073 (15)
C8	0.0257 (19)	0.0221 (17)	0.0311 (19)	−0.0081 (15)	−0.0016 (15)	−0.0047 (15)
C9	0.030 (2)	0.048 (2)	0.035 (2)	−0.0078 (18)	−0.0039 (17)	−0.0168 (18)
C10	0.036 (2)	0.048 (2)	0.032 (2)	−0.0031 (19)	−0.0032 (18)	−0.0155 (18)
C11	0.028 (2)	0.0266 (19)	0.036 (2)	−0.0076 (16)	0.0033 (16)	−0.0049 (16)
C12	0.027 (2)	0.050 (2)	0.050 (2)	−0.0111 (19)	−0.0040 (18)	−0.018 (2)
C13	0.027 (2)	0.054 (3)	0.039 (2)	−0.0119 (19)	−0.0026 (17)	−0.0247 (19)
C14	0.0221 (18)	0.0295 (19)	0.0270 (18)	−0.0080 (15)	−0.0046 (14)	−0.0098 (15)
C15	0.027 (2)	0.039 (2)	0.0253 (18)	−0.0134 (17)	−0.0032 (15)	−0.0096 (16)
C16	0.025 (2)	0.037 (2)	0.0259 (18)	−0.0096 (17)	−0.0037 (15)	−0.0072 (16)
C17	0.038 (2)	0.049 (2)	0.028 (2)	−0.020 (2)	0.0007 (17)	−0.0109 (18)
C18	0.035 (2)	0.073 (3)	0.037 (2)	−0.026 (2)	0.0066 (19)	−0.024 (2)
C19	0.026 (2)	0.062 (3)	0.054 (3)	−0.003 (2)	−0.001 (2)	−0.032 (2)
C20	0.026 (2)	0.042 (2)	0.041 (2)	−0.0053 (18)	−0.0057 (17)	−0.0149 (18)
C21	0.131 (5)	0.086 (4)	0.029 (2)	−0.063 (4)	0.027 (3)	−0.013 (2)

Geometric parameters (Å, º) top

Br1—C3	1.900 (3)	C9—C10	1.514 (5)
Br2—C5	1.895 (3)	C9—H9A	0.9700
O1—C11	1.423 (4)	C9—H9B	0.9700
O1—H1	0.8200	C10—C11	1.499 (5)
O2—C16	1.364 (4)	C10—H10A	0.9700
O2—H2	0.8200	C10—H10B	0.9700
O3—C17	1.363 (4)	C11—C12	1.509 (5)
O3—C21	1.416 (4)	C11—H11	0.9800
N1—C2	1.381 (4)	C12—C13	1.520 (5)
N1—C14	1.448 (4)	C12—H12A	0.9700
N1—H1A	0.8600	C12—H12B	0.9700
N2—C14	1.476 (4)	C13—H13A	0.9700
N2—C7	1.482 (4)	C13—H13B	0.9700
N2—C8	1.490 (4)	C14—C15	1.535 (4)
C1—C6	1.389 (4)	C14—H14	0.9800
C1—C2	1.396 (4)	C15—C16	1.385 (5)
C1—C7	1.517 (4)	C15—C20	1.388 (5)
C2—C3	1.395 (5)	C16—C17	1.397 (5)
C3—C4	1.376 (4)	C17—C18	1.381 (5)
C4—C5	1.376 (5)	C18—C19	1.391 (6)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.374 (5)	C19—C20	1.379 (5)
C6—H6	0.9300	C19—H19	0.9300
C7—H7A	0.9700	C20—H20	0.9300
C7—H7B	0.9700	C21—H21A	0.9600
C8—C9	1.513 (5)	C21—H21B	0.9600
C8—C13	1.518 (4)	C21—H21C	0.9600
C8—H8	0.9800

C11—O1—H1	109.5	H10A—C10—H10B	107.9
C16—O2—H2	109.5	O1—C11—C10	107.9 (3)
C17—O3—C21	117.3 (3)	O1—C11—C12	112.8 (3)
C2—N1—C14	120.0 (3)	C10—C11—C12	109.8 (3)
C2—N1—H1A	120.0	O1—C11—H11	108.8
C14—N1—H1A	120.0	C10—C11—H11	108.8
C14—N2—C7	107.0 (2)	C12—C11—H11	108.8
C14—N2—C8	112.1 (2)	C11—C12—C13	110.9 (3)
C7—N2—C8	116.3 (2)	C11—C12—H12A	109.5
C6—C1—C2	120.2 (3)	C13—C12—H12A	109.5
C6—C1—C7	121.4 (3)	C11—C12—H12B	109.5
C2—C1—C7	118.4 (3)	C13—C12—H12B	109.5
N1—C2—C3	121.7 (3)	H12A—C12—H12B	108.1
N1—C2—C1	120.4 (3)	C8—C13—C12	112.7 (3)
C3—C2—C1	118.0 (3)	C8—C13—H13A	109.1
C4—C3—C2	121.9 (3)	C12—C13—H13A	109.1
C4—C3—Br1	118.5 (3)	C8—C13—H13B	109.1
C2—C3—Br1	119.6 (3)	C12—C13—H13B	109.1
C5—C4—C3	118.9 (3)	H13A—C13—H13B	107.8
C5—C4—H4	120.6	N1—C14—N2	113.6 (3)
C3—C4—H4	120.6	N1—C14—C15	113.8 (3)
C6—C5—C4	121.1 (3)	N2—C14—C15	109.0 (3)
C6—C5—Br2	119.3 (3)	N1—C14—H14	106.7
C4—C5—Br2	119.6 (3)	N2—C14—H14	106.7
C5—C6—C1	119.9 (3)	C15—C14—H14	106.7
C5—C6—H6	120.0	C16—C15—C20	118.9 (3)
C1—C6—H6	120.0	C16—C15—C14	118.9 (3)
N2—C7—C1	111.6 (3)	C20—C15—C14	122.1 (3)
N2—C7—H7A	109.3	O2—C16—C15	122.2 (3)
C1—C7—H7A	109.3	O2—C16—C17	116.8 (3)
N2—C7—H7B	109.3	C15—C16—C17	121.0 (3)
C1—C7—H7B	109.3	O3—C17—C18	126.0 (3)
H7A—C7—H7B	108.0	O3—C17—C16	114.9 (3)
N2—C8—C9	112.9 (3)	C18—C17—C16	119.1 (4)
N2—C8—C13	108.8 (3)	C17—C18—C19	120.2 (4)
C9—C8—C13	109.3 (3)	C17—C18—H18	119.9
N2—C8—H8	108.6	C19—C18—H18	119.9
C9—C8—H8	108.6	C20—C19—C18	120.1 (4)
C13—C8—H8	108.6	C20—C19—H19	120.0
C8—C9—C10	112.0 (3)	C18—C19—H19	120.0
C8—C9—H9A	109.2	C19—C20—C15	120.6 (4)
C10—C9—H9A	109.2	C19—C20—H20	119.7
C8—C9—H9B	109.2	C15—C20—H20	119.7
C10—C9—H9B	109.2	O3—C21—H21A	109.5
H9A—C9—H9B	107.9	O3—C21—H21B	109.5
C11—C10—C9	112.0 (3)	H21A—C21—H21B	109.5
C11—C10—H10A	109.2	O3—C21—H21C	109.5
C9—C10—H10A	109.2	H21A—C21—H21C	109.5
C11—C10—H10B	109.2	H21B—C21—H21C	109.5
C9—C10—H10B	109.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.89	2.614 (3)	147
O1—H1···O3ⁱ	0.82	2.41	3.048 (4)	135
O1—H1···O2ⁱ	0.82	2.13	2.897 (4)	155

Symmetry code: (i) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄Br₂N₂O₃
M_r	512.24
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.695 (2), 11.124 (3), 12.090 (2)
α, β, γ (°)	73.870 (3), 78.226 (3), 67.031 (2)
V (Å³)	1028.2 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.97
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Bruker SMART CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.382, 0.382
No. of measured, independent and observed [I > 2σ(I)] reflections	8514, 4305, 3035
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.096, 1.02
No. of reflections	4305
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.41

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.89	2.614 (3)	146.5
O1—H1···O3ⁱ	0.82	2.41	3.048 (4)	135.3
O1—H1···O2ⁱ	0.82	2.13	2.897 (4)	154.6

Symmetry code: (i) −x+1, −y+2, −z.

Acknowledgements

Financial support from the Third Affiliated Hospital of Soochow University is acknowledged.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Felix, F. S., Brett, C. M. A. & Angnes, L. (2008). Talanta, 76, 128–133. Web of Science CrossRef PubMed CAS Google Scholar
Gaida, W., Klinder, K., Arndt, K. & Weiser, T. (2005). Neuropharmacology, 49, 1220–1227. Web of Science CrossRef PubMed CAS Google Scholar
Lee, H. J., Joung, S. K., Kim, Y. G., Yoo, J.-Y. & Han, S. B. (2004). Pharm. Res. 49, 93–98. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). 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

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Volume 65| Part 3| March 2009| Page o550

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

2-[6,8-Di­bromo-3-(4-hy­droxy­cyclo­hexyl)-1,2,3,4-tetra­hydro­quinazolin-2-yl]-6-meth­oxy­phenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[6,8-Dibromo-3-(4-hydroxycyclohexyl)-1,2,3,4-tetrahydroquinazolin-2-yl]-6-methoxyphenol