4-[6,8-Dibromo-2-(2-chloro-5-nitro­phen­yl)-1,2,3,4-tetra­hydro­quinazolin-3-yl]cyclo­hexa­nol

Wang, Z.-G.; Xia, Z.-L.; Wang, R.; Wang, M.-L.

doi:10.1107/S1600536810015023

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages o1205-o1206

https://doi.org/10.1107/S1600536810015023

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4-[6,8-Dibromo-2-(2-chloro-5-nitrophenyl)-1,2,3,4-tetrahydroquinazolin-3-yl]cyclohexanol

Zhi-Gang Wang,^a Zong-Lin Xia,^b Rong Wang ^c and Ming-Li Wang ^b ^*

^aDepartment of Respiratory Medicine, Third Affiliated Hospital of Soochow University, Changzhou 213003, People's Republic of China, ^bDepartment of Pharmacy, Third Affiliated Hospital of Soochow University, Changzhou 213003, People's Republic of China, and ^cModern Medical Research Center, Third Affiliated Hospital of Soochow University, Changzhou 213003, People's Republic of China
^*Correspondence e-mail: wangmingli09@yahoo.com.cn

(Received 16 March 2010; accepted 23 April 2010; online 28 April 2010)

The title compound, C₂₀H₂₀Br₂ClN₃O₃, was synthesized by the condensation reaction of 2-chloro-5-nitrobenzaldehyde with 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol in a methanol solution. There are two independent molecules in the asymmetric unit and in one molecule the atoms of the cyclohexane ring are disordered over two sets of sites with refined occupancies of 0.657 (12) and 0.343 (12). The dihedral angle between the two benzene rings is 89.5 (2)° in one molecule and 82.9 (2)° in the other. In the crystal structure, intermolecular N—H⋯O and O—H⋯O hydrogen bonds link the molecules into chains propagating along [01 $[\overline{1}]$ ].

Related literature

For details of the pharmaceutical uses of Ambroxol, systematic name 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol, a compound closely related to the title compound see: Felix et al. (2008 ); Gaida et al. (2005 ); Lee et al. (2004 ). For a related structure, see: Wang et al. (2009 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₀H₂₀Br₂ClN₃O₃
M_r = 545.66
Triclinic, $[P \overline 1]$
a = 10.2614 (13) Å
b = 13.1418 (17) Å
c = 16.931 (2) Å
α = 83.764 (2)°
β = 73.309 (2)°
γ = 84.750 (2)°
V = 2169.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 3.89 mm⁻¹
T = 298 K
0.30 × 0.28 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.389, T_max = 0.409
11972 measured reflections
8470 independent reflections
4874 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.154
S = 1.02
8470 reflections
578 parameters
122 restraints
H-atom parameters constrained
Δρ_max = 1.56 e Å⁻³
Δρ_min = −1.07 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O4ⁱ	0.86	2.33	2.942 (7)	129
O3—H3⋯O6′ⁱⁱ	0.84	1.89	2.713 (12)	166
O6—H6⋯O3ⁱⁱⁱ	0.84	2.04	2.877 (17)	179
O6′—H6′⋯O3ⁱⁱⁱ	0.84	1.85	2.694 (10)	179
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z; (iii) x-1, y, 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: https://doi.org/10.1107/S1600536810015023/lh5014sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015023/lh5014Isup2.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). Recently, we reported the crystal structure of a derivative of Ambroxol (Wang et al., 2009). In this paper, the crystal structure of the title compound, derived from the condensation reaction of 2-chloro-5-nitrobenzaldehyde with 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol in methanol solution, is reported.

There are two independent molecules in the asymmetric unit of the title compound, Fig. 1. The dihedral angle between the two benzene rings is 89.5 (2)° in one molecule and 82.9 (2)° in the other. The cyclohexyl rings adopt chair configurations. All bond lengths are within normal ranges (Allen et al., 1987).

Related literature top

For details of the pharmaceutical uses of Ambroxol, systematic name 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol, a compound closely related to the title compound see: Felix et al. (2008); Gaida et al. (2005); Lee et al. (2004). For a related structure, see: Wang et al. (2009). For standard bond-length data, see: Allen et al. (1987).

Experimental top

2-Chloro-5-nitrobenzaldehyde (1.0 mol, 185.6 mg) and 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol (1.0 mmol, 378.1 mg) were dissolved in a methanol solution (30 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.

Structure description top

For details of the pharmaceutical uses of Ambroxol, systematic name 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol, a compound closely related to the title compound see: Felix et al. (2008); Gaida et al. (2005); Lee et al. (2004). For a related structure, see: Wang et al. (2009). For standard bond-length data, see: Allen et al. (1987).

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 asymmetric unit of the title compound showing 30% probability ellipsoids. H atoms bonded to C atoms are not shown.

4-[6,8-Dibromo-2-(2-chloro-5-nitrophenyl)-1,2,3,4-tetrahydroquinazolin- 3-yl]cyclohexanol top

Crystal data top

C₂₀H₂₀Br₂ClN₃O₃	Z = 4
M_r = 545.66	F(000) = 1088
Triclinic, P1	D_x = 1.670 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2614 (13) Å	Cell parameters from 2646 reflections
b = 13.1418 (17) Å	θ = 2.5–24.5°
c = 16.931 (2) Å	µ = 3.89 mm⁻¹
α = 83.764 (2)°	T = 298 K
β = 73.309 (2)°	Block, colorless
γ = 84.750 (2)°	0.30 × 0.28 × 0.28 mm
V = 2169.8 (5) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	8470 independent reflections
Radiation source: fine-focus sealed tube	4874 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 26.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→7
T_min = 0.389, T_max = 0.409	k = −15→16
11972 measured reflections	l = −21→20

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0631P)² + 2.7275P] where P = (F_o² + 2F_c²)/3
8470 reflections	(Δ/σ)_max = 0.001
578 parameters	Δρ_max = 1.56 e Å⁻³
122 restraints	Δρ_min = −1.07 e Å⁻³

Crystal data top

C₂₀H₂₀Br₂ClN₃O₃	γ = 84.750 (2)°
M_r = 545.66	V = 2169.8 (5) Å³
Triclinic, P1	Z = 4
a = 10.2614 (13) Å	Mo Kα radiation
b = 13.1418 (17) Å	µ = 3.89 mm⁻¹
c = 16.931 (2) Å	T = 298 K
α = 83.764 (2)°	0.30 × 0.28 × 0.28 mm
β = 73.309 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	8470 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4874 reflections with I > 2σ(I)
T_min = 0.389, T_max = 0.409	R_int = 0.022
11972 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	122 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.02	Δρ_max = 1.56 e Å⁻³
8470 reflections	Δρ_min = −1.07 e Å⁻³
578 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Br1	0.39058 (9)	−0.05133 (6)	0.42693 (4)	0.0888 (3)
Br2	−0.06018 (7)	0.08773 (7)	0.30819 (7)	0.1156 (4)
Br3	0.65212 (7)	0.61194 (6)	0.35191 (6)	0.0919 (3)
Br4	0.59092 (6)	0.18627 (5)	0.36046 (5)	0.0747 (2)
Cl1	0.87128 (15)	−0.09542 (13)	0.01005 (10)	0.0700 (4)
Cl2	−0.17164 (14)	0.27481 (12)	0.47738 (9)	0.0628 (4)
O1	0.4691 (6)	−0.4725 (4)	0.1616 (4)	0.133 (3)
O2	0.3509 (5)	−0.3554 (4)	0.2309 (4)	0.0953 (16)
O3	0.8184 (5)	0.4244 (3)	0.0419 (3)	0.0816 (14)
H3	0.8561	0.4573	−0.0030	0.122*
O4	0.2375 (7)	0.1609 (5)	0.7120 (4)	0.119 (2)
O5	0.0491 (7)	0.1570 (6)	0.8042 (4)	0.145 (3)
N1	0.4516 (6)	−0.3856 (4)	0.1802 (4)	0.0731 (15)
N2	0.5854 (4)	0.0384 (3)	0.0978 (3)	0.0435 (10)
N3	0.5434 (4)	−0.0321 (3)	0.2395 (2)	0.0472 (11)
H3N	0.5793	−0.0464	0.2797	0.057*
N4	0.1168 (8)	0.1719 (5)	0.7331 (4)	0.0849 (18)
N5	0.1019 (4)	0.3814 (3)	0.4122 (2)	0.0425 (10)
N6	0.2870 (4)	0.2572 (3)	0.4237 (3)	0.0557 (12)
H6N	0.3209	0.1949	0.4251	0.067*
C1	0.3494 (5)	0.0295 (4)	0.1906 (3)	0.0469 (13)
C2	0.4071 (6)	−0.0031 (4)	0.2565 (3)	0.0482 (13)
C3	0.3189 (7)	−0.0040 (4)	0.3370 (3)	0.0579 (15)
C4	0.1815 (7)	0.0235 (4)	0.3527 (4)	0.0704 (19)
H4	0.1251	0.0217	0.4067	0.085*
C5	0.1303 (6)	0.0533 (5)	0.2873 (5)	0.0723 (19)
C6	0.2116 (6)	0.0578 (4)	0.2078 (4)	0.0598 (16)
H6B	0.1740	0.0801	0.1646	0.072*
C7	0.4418 (5)	0.0291 (4)	0.1042 (3)	0.0483 (13)
H7A	0.4333	−0.0342	0.0819	0.058*
H7B	0.4119	0.0854	0.0702	0.058*
C8	0.6281 (5)	−0.0394 (4)	0.1557 (3)	0.0407 (12)
H8	0.7206	−0.0254	0.1549	0.049*
C9	0.6166 (6)	0.1452 (4)	0.1032 (4)	0.0569 (15)
H9	0.5423	0.1758	0.1462	0.068*
C10	0.6231 (9)	0.2061 (5)	0.0216 (5)	0.097 (3)
H10A	0.5357	0.2064	0.0102	0.116*
H10B	0.6912	0.1731	−0.0221	0.116*
C11	0.6590 (10)	0.3179 (6)	0.0215 (6)	0.111 (3)
H11A	0.6649	0.3539	−0.0324	0.133*
H11B	0.5873	0.3528	0.0622	0.133*
C12	0.7856 (8)	0.3205 (5)	0.0402 (4)	0.078 (2)
H12	0.8577	0.2879	−0.0027	0.093*
C13	0.7829 (8)	0.2642 (5)	0.1224 (5)	0.086 (2)
H13A	0.7152	0.2978	0.1659	0.103*
H13B	0.8711	0.2656	0.1325	0.103*
C14	0.7484 (7)	0.1518 (5)	0.1241 (4)	0.0737 (19)
H14A	0.8216	0.1165	0.0847	0.088*
H14B	0.7417	0.1176	0.1787	0.088*
C15	0.6360 (5)	−0.1458 (4)	0.1260 (3)	0.0410 (12)
C16	0.5412 (5)	−0.2159 (4)	0.1637 (3)	0.0465 (13)
H16	0.4664	−0.1973	0.2069	0.056*
C17	0.5551 (6)	−0.3135 (4)	0.1386 (3)	0.0511 (13)
C18	0.6655 (6)	−0.3457 (5)	0.0763 (4)	0.0662 (17)
H18	0.6752	−0.4123	0.0607	0.079*
C19	0.7607 (6)	−0.2758 (5)	0.0380 (4)	0.0614 (16)
H19	0.8361	−0.2950	−0.0045	0.074*
C20	0.7458 (5)	−0.1784 (4)	0.0618 (3)	0.0487 (13)
C21	0.3193 (5)	0.4363 (4)	0.4205 (3)	0.0445 (12)
C22	0.3731 (5)	0.3365 (4)	0.4085 (3)	0.0443 (12)
C23	0.5137 (5)	0.3210 (4)	0.3792 (3)	0.0481 (13)
C24	0.5984 (6)	0.4014 (5)	0.3633 (3)	0.0586 (16)
H24	0.6925	0.3895	0.3440	0.070*
C25	0.5415 (6)	0.4989 (5)	0.3765 (4)	0.0595 (15)
C26	0.4024 (6)	0.5159 (4)	0.4057 (3)	0.0539 (14)
H26	0.3647	0.5820	0.4155	0.065*
C27	0.1651 (5)	0.4519 (4)	0.4489 (3)	0.0449 (12)
H27A	0.1338	0.4407	0.5087	0.054*
H27B	0.1378	0.5220	0.4331	0.054*
C28	0.1395 (5)	0.2766 (4)	0.4373 (3)	0.0463 (13)
H28	0.1110	0.2319	0.4034	0.056*
O6	0.0678 (19)	0.4493 (13)	0.0811 (8)	0.057 (4)	0.343 (12)
H6	−0.0051	0.4425	0.0696	0.085*	0.343 (12)
C29	0.1191 (7)	0.4085 (5)	0.3235 (3)	0.079 (2)	0.343 (12)
H29A	0.1792	0.4634	0.3210	0.095*	0.343 (12)
C30	0.0096 (19)	0.4808 (16)	0.3083 (8)	0.052 (8)	0.343 (12)
H30A	0.0273	0.5481	0.3197	0.062*	0.343 (12)
H30B	−0.0748	0.4616	0.3485	0.062*	0.343 (12)
C31	−0.0137 (17)	0.4906 (19)	0.2262 (8)	0.067 (6)	0.343 (12)
H31A	−0.0412	0.5617	0.2137	0.080*	0.343 (12)
H31B	−0.0896	0.4502	0.2290	0.080*	0.343 (12)
C32	0.1012 (18)	0.4595 (13)	0.1567 (7)	0.065 (6)	0.343 (12)
H32A	0.1618	0.5162	0.1437	0.078*	0.343 (12)
C33	0.1854 (18)	0.3684 (13)	0.1758 (7)	0.053 (6)	0.343 (12)
H33A	0.1398	0.3080	0.1731	0.063*	0.343 (12)
H33B	0.2713	0.3671	0.1327	0.063*	0.343 (12)
C34	0.2156 (15)	0.3599 (13)	0.2562 (6)	0.057 (5)	0.343 (12)
H34A	0.2257	0.2876	0.2737	0.068*	0.343 (12)
H34B	0.3032	0.3881	0.2476	0.068*	0.343 (12)
O6'	0.0198 (12)	0.4810 (10)	0.0975 (6)	0.095 (4)	0.657 (12)
H6'	−0.0436	0.4642	0.0802	0.142*	0.657 (12)
C29'	0.1191 (7)	0.4085 (5)	0.3235 (3)	0.079 (2)	0.657 (12)
H29B	0.2138	0.4277	0.3026	0.095*	0.657 (12)
C30'	0.0385 (12)	0.5058 (7)	0.3093 (5)	0.049 (3)	0.657 (12)
H30C	0.0738	0.5610	0.3292	0.059*	0.657 (12)
H30D	−0.0552	0.4992	0.3425	0.059*	0.657 (12)
C31'	0.0389 (12)	0.5356 (7)	0.2214 (5)	0.067 (3)	0.657 (12)
H31C	−0.0314	0.5897	0.2198	0.081*	0.657 (12)
H31D	0.1262	0.5619	0.1908	0.081*	0.657 (12)
C32'	0.0143 (13)	0.4461 (8)	0.1814 (6)	0.081 (4)	0.657 (12)
H32B	−0.0764	0.4224	0.2101	0.098*	0.657 (12)
C33'	0.1193 (15)	0.3608 (7)	0.1855 (5)	0.077 (4)	0.657 (12)
H33C	0.2091	0.3839	0.1565	0.092*	0.657 (12)
H33D	0.1037	0.3037	0.1583	0.092*	0.657 (12)
C34'	0.1142 (13)	0.3259 (6)	0.2735 (5)	0.072 (3)	0.657 (12)
H34C	0.0309	0.2912	0.2989	0.087*	0.657 (12)
H34D	0.1902	0.2764	0.2739	0.087*	0.657 (12)
C35	0.0602 (5)	0.2507 (4)	0.5269 (3)	0.0420 (12)
C36	0.1226 (6)	0.2241 (4)	0.5892 (4)	0.0519 (14)
H36	0.2172	0.2205	0.5769	0.062*
C37	0.0451 (7)	0.2028 (4)	0.6695 (4)	0.0570 (15)
C38	−0.0942 (7)	0.2086 (4)	0.6919 (4)	0.0617 (16)
H38	−0.1444	0.1964	0.7469	0.074*
C39	−0.1569 (6)	0.2328 (4)	0.6310 (3)	0.0516 (14)
H39	−0.2515	0.2360	0.6442	0.062*
C40	−0.0820 (5)	0.2523 (4)	0.5505 (3)	0.0435 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1211 (7)	0.0938 (6)	0.0491 (4)	−0.0380 (5)	−0.0139 (4)	0.0028 (3)
Br2	0.0488 (4)	0.0931 (6)	0.1853 (10)	0.0068 (4)	0.0052 (5)	−0.0404 (6)
Br3	0.0649 (4)	0.0829 (5)	0.1281 (7)	−0.0302 (4)	−0.0261 (4)	0.0094 (5)
Br4	0.0500 (4)	0.0687 (4)	0.0959 (5)	0.0196 (3)	−0.0086 (3)	−0.0173 (4)
Cl1	0.0529 (9)	0.0799 (11)	0.0661 (10)	−0.0119 (8)	0.0041 (8)	−0.0084 (8)
Cl2	0.0496 (8)	0.0840 (11)	0.0619 (9)	−0.0129 (7)	−0.0264 (7)	−0.0010 (8)
O1	0.120 (5)	0.060 (3)	0.193 (7)	−0.028 (3)	0.019 (4)	−0.048 (4)
O2	0.073 (3)	0.074 (3)	0.120 (4)	−0.024 (3)	0.013 (3)	−0.020 (3)
O3	0.106 (4)	0.048 (3)	0.083 (3)	−0.029 (2)	−0.010 (3)	0.002 (2)
O4	0.096 (4)	0.143 (5)	0.134 (5)	−0.020 (4)	−0.076 (4)	0.052 (4)
O5	0.147 (6)	0.219 (8)	0.072 (4)	−0.013 (5)	−0.056 (4)	0.040 (4)
N1	0.073 (4)	0.048 (3)	0.094 (4)	−0.014 (3)	−0.011 (3)	−0.012 (3)
N2	0.046 (2)	0.038 (2)	0.048 (3)	−0.0040 (19)	−0.015 (2)	−0.004 (2)
N3	0.055 (3)	0.051 (3)	0.037 (2)	0.004 (2)	−0.017 (2)	−0.006 (2)
N4	0.099 (5)	0.081 (4)	0.085 (5)	−0.012 (4)	−0.052 (4)	0.022 (3)
N5	0.040 (2)	0.045 (3)	0.042 (2)	0.0008 (19)	−0.0101 (19)	−0.0040 (19)
N6	0.042 (3)	0.038 (3)	0.079 (3)	0.006 (2)	−0.005 (2)	−0.010 (2)
C1	0.047 (3)	0.036 (3)	0.057 (3)	−0.001 (2)	−0.014 (3)	−0.009 (3)
C2	0.059 (3)	0.031 (3)	0.053 (3)	−0.008 (2)	−0.008 (3)	−0.010 (2)
C3	0.076 (4)	0.040 (3)	0.050 (3)	−0.014 (3)	−0.002 (3)	−0.006 (3)
C4	0.068 (4)	0.050 (4)	0.072 (5)	−0.015 (3)	0.023 (4)	−0.021 (3)
C5	0.049 (4)	0.055 (4)	0.101 (6)	0.001 (3)	0.003 (4)	−0.022 (4)
C6	0.052 (3)	0.044 (3)	0.084 (5)	0.002 (3)	−0.015 (3)	−0.016 (3)
C7	0.049 (3)	0.043 (3)	0.056 (3)	0.002 (2)	−0.021 (3)	−0.004 (3)
C8	0.040 (3)	0.040 (3)	0.044 (3)	−0.001 (2)	−0.016 (2)	−0.003 (2)
C9	0.063 (4)	0.048 (3)	0.063 (4)	−0.005 (3)	−0.023 (3)	−0.001 (3)
C10	0.142 (7)	0.068 (5)	0.106 (6)	−0.036 (5)	−0.080 (6)	0.023 (4)
C11	0.148 (8)	0.072 (5)	0.141 (8)	−0.035 (5)	−0.094 (7)	0.039 (5)
C12	0.099 (5)	0.060 (4)	0.070 (4)	−0.031 (4)	−0.012 (4)	0.005 (3)
C13	0.110 (6)	0.073 (5)	0.088 (5)	−0.035 (4)	−0.045 (5)	0.004 (4)
C14	0.079 (5)	0.067 (4)	0.082 (5)	−0.022 (4)	−0.037 (4)	0.014 (4)
C15	0.043 (3)	0.041 (3)	0.040 (3)	0.001 (2)	−0.014 (2)	−0.001 (2)
C16	0.047 (3)	0.044 (3)	0.048 (3)	0.001 (2)	−0.013 (3)	−0.005 (2)
C17	0.052 (3)	0.041 (3)	0.059 (4)	−0.002 (3)	−0.014 (3)	−0.006 (3)
C18	0.070 (4)	0.047 (4)	0.078 (4)	0.007 (3)	−0.012 (4)	−0.021 (3)
C19	0.056 (4)	0.065 (4)	0.052 (4)	0.003 (3)	0.004 (3)	−0.018 (3)
C20	0.043 (3)	0.051 (3)	0.048 (3)	0.000 (2)	−0.008 (3)	−0.004 (3)
C21	0.044 (3)	0.042 (3)	0.046 (3)	0.002 (2)	−0.014 (2)	0.000 (2)
C22	0.045 (3)	0.042 (3)	0.044 (3)	0.003 (2)	−0.013 (2)	0.001 (2)
C23	0.041 (3)	0.056 (3)	0.044 (3)	0.004 (3)	−0.010 (2)	−0.003 (3)
C24	0.036 (3)	0.081 (5)	0.058 (4)	−0.001 (3)	−0.016 (3)	0.003 (3)
C25	0.049 (3)	0.062 (4)	0.066 (4)	−0.012 (3)	−0.016 (3)	0.004 (3)
C26	0.053 (3)	0.050 (3)	0.058 (4)	−0.005 (3)	−0.014 (3)	−0.003 (3)
C27	0.041 (3)	0.036 (3)	0.052 (3)	−0.001 (2)	−0.006 (3)	−0.004 (2)
C28	0.042 (3)	0.043 (3)	0.054 (3)	−0.002 (2)	−0.013 (3)	−0.007 (3)
O6	0.080 (8)	0.053 (7)	0.038 (7)	0.013 (6)	−0.021 (6)	−0.010 (5)
C29	0.095 (5)	0.086 (5)	0.056 (4)	0.039 (4)	−0.028 (4)	−0.021 (4)
C30	0.055 (10)	0.053 (10)	0.045 (10)	0.000 (8)	−0.011 (7)	−0.007 (7)
C31	0.072 (10)	0.074 (10)	0.056 (9)	0.013 (8)	−0.027 (8)	−0.002 (8)
C32	0.099 (18)	0.061 (13)	0.038 (11)	0.000 (12)	−0.025 (12)	−0.005 (9)
C33	0.040 (11)	0.080 (14)	0.038 (10)	−0.002 (9)	−0.010 (8)	−0.009 (9)
C34	0.045 (10)	0.070 (12)	0.053 (11)	0.010 (9)	−0.013 (9)	−0.009 (9)
O6'	0.114 (7)	0.125 (8)	0.053 (5)	−0.037 (6)	−0.030 (5)	0.003 (5)
C29'	0.095 (5)	0.086 (5)	0.056 (4)	0.039 (4)	−0.028 (4)	−0.021 (4)
C30'	0.060 (6)	0.043 (6)	0.050 (6)	−0.006 (5)	−0.021 (5)	−0.009 (4)
C31'	0.066 (6)	0.076 (6)	0.063 (6)	−0.006 (5)	−0.027 (5)	0.004 (5)
C32'	0.079 (9)	0.139 (12)	0.029 (6)	−0.050 (9)	−0.015 (6)	0.020 (6)
C33'	0.103 (9)	0.077 (7)	0.047 (6)	−0.022 (6)	−0.009 (6)	−0.011 (5)
C34'	0.092 (7)	0.061 (6)	0.067 (6)	−0.012 (5)	−0.027 (5)	0.003 (5)
C35	0.042 (3)	0.036 (3)	0.050 (3)	0.002 (2)	−0.017 (3)	−0.009 (2)
C36	0.046 (3)	0.041 (3)	0.069 (4)	0.003 (2)	−0.022 (3)	0.001 (3)
C37	0.075 (4)	0.046 (3)	0.058 (4)	−0.002 (3)	−0.036 (3)	0.007 (3)
C38	0.075 (4)	0.050 (4)	0.055 (4)	−0.005 (3)	−0.013 (3)	0.004 (3)
C39	0.049 (3)	0.054 (3)	0.050 (3)	−0.002 (3)	−0.014 (3)	0.000 (3)
C40	0.044 (3)	0.040 (3)	0.051 (3)	−0.001 (2)	−0.020 (3)	−0.005 (2)

Geometric parameters (Å, º) top

Br1—C3	1.897 (6)	C18—H18	0.9300
Br2—C5	1.904 (6)	C19—C20	1.365 (8)
Br3—C25	1.890 (6)	C19—H19	0.9300
Br4—C23	1.893 (5)	C21—C26	1.367 (7)
Cl1—C20	1.737 (5)	C21—C22	1.387 (7)
Cl2—C40	1.729 (5)	C21—C27	1.517 (7)
O1—N1	1.201 (6)	C22—C23	1.388 (7)
O2—N1	1.204 (7)	C23—C24	1.384 (8)
O3—C12	1.441 (7)	C24—C25	1.373 (8)
O3—H3	0.8401	C24—H24	0.9300
O4—N4	1.186 (8)	C25—C26	1.375 (8)
O5—N4	1.210 (8)	C26—H26	0.9300
N1—C17	1.460 (7)	C27—H27A	0.9700
N2—C7	1.461 (6)	C27—H27B	0.9700
N2—C8	1.464 (6)	C28—C35	1.519 (7)
N2—C9	1.487 (7)	C28—H28	0.9800
N3—C2	1.371 (7)	O6—C32	1.439 (10)
N3—C8	1.444 (6)	O6—H6	0.8401
N3—H3N	0.8600	O6—H6'	1.1466
N4—C37	1.472 (8)	C29—C34	1.442 (8)
N5—C28	1.448 (6)	C29—C30	1.466 (8)
N5—C27	1.460 (6)	C29—H29A	0.9800
N5—C29	1.470 (7)	C30—C31	1.468 (9)
N6—C22	1.383 (6)	C30—H30A	0.9700
N6—C28	1.467 (6)	C30—H30B	0.9700
N6—H6N	0.8600	C31—C32	1.469 (9)
C1—C6	1.383 (7)	C31—H31A	0.9700
C1—C2	1.416 (7)	C31—H31B	0.9700
C1—C7	1.499 (7)	C32—C33	1.474 (9)
C2—C3	1.403 (8)	C32—H32A	0.9800
C3—C4	1.379 (9)	C33—C34	1.470 (9)
C4—C5	1.364 (9)	C33—H33A	0.9700
C4—H4	0.9300	C33—H33B	0.9700
C5—C6	1.363 (9)	C34—H34A	0.9700
C6—H6B	0.9300	C34—H34B	0.9700
C7—H7A	0.9700	O6'—C32'	1.432 (12)
C7—H7B	0.9700	O6'—H6	0.8290
C8—C15	1.525 (7)	O6'—H6'	0.8401
C8—H8	0.9800	C30'—C31'	1.496 (7)
C9—C14	1.505 (8)	C30'—H30C	0.9700
C9—C10	1.507 (8)	C30'—H30D	0.9700
C9—H9	0.9800	C31'—C32'	1.494 (7)
C10—C11	1.548 (9)	C31'—H31C	0.9700
C10—H10A	0.9700	C31'—H31D	0.9700
C10—H10B	0.9700	C32'—C33'	1.492 (8)
C11—C12	1.427 (10)	C32'—H32B	0.9800
C11—H11A	0.9700	C33'—C34'	1.497 (7)
C11—H11B	0.9700	C33'—H33C	0.9700
C12—C13	1.497 (9)	C33'—H33D	0.9700
C12—H12	0.9800	C34'—H34C	0.9700
C13—C14	1.545 (9)	C34'—H34D	0.9700
C13—H13A	0.9700	C35—C36	1.382 (7)
C13—H13B	0.9700	C35—C40	1.397 (7)
C14—H14A	0.9700	C36—C37	1.377 (8)
C14—H14B	0.9700	C36—H36	0.9300
C15—C16	1.372 (7)	C37—C38	1.367 (8)
C15—C20	1.394 (7)	C38—C39	1.360 (8)
C16—C17	1.376 (7)	C38—H38	0.9300
C16—H16	0.9300	C39—C40	1.369 (7)
C17—C18	1.378 (8)	C39—H39	0.9300
C18—C19	1.375 (8)

C12—O3—H3	118.6	C24—C23—C22	121.7 (5)
O1—N1—O2	122.5 (6)	C24—C23—Br4	119.4 (4)
O1—N1—C17	118.7 (6)	C22—C23—Br4	118.9 (4)
O2—N1—C17	118.8 (5)	C25—C24—C23	119.0 (5)
C7—N2—C8	109.3 (4)	C25—C24—H24	120.5
C7—N2—C9	112.8 (4)	C23—C24—H24	120.5
C8—N2—C9	115.5 (4)	C24—C25—C26	120.2 (5)
C2—N3—C8	121.6 (4)	C24—C25—Br3	120.6 (4)
C2—N3—H3N	119.2	C26—C25—Br3	119.1 (5)
C8—N3—H3N	119.2	C21—C26—C25	120.5 (5)
O4—N4—O5	123.2 (7)	C21—C26—H26	119.8
O4—N4—C37	118.6 (7)	C25—C26—H26	119.8
O5—N4—C37	118.1 (7)	N5—C27—C21	110.9 (4)
C28—N5—C27	109.7 (4)	N5—C27—H27A	109.5
C28—N5—C29	117.3 (4)	C21—C27—H27A	109.5
C27—N5—C29	112.7 (4)	N5—C27—H27B	109.5
C22—N6—C28	121.7 (4)	C21—C27—H27B	109.5
C22—N6—H6N	119.2	H27A—C27—H27B	108.1
C28—N6—H6N	119.2	N5—C28—N6	112.7 (4)
C6—C1—C2	119.6 (5)	N5—C28—C35	109.0 (4)
C6—C1—C7	122.8 (5)	N6—C28—C35	112.2 (4)
C2—C1—C7	117.6 (5)	N5—C28—H28	107.6
N3—C2—C3	123.3 (5)	N6—C28—H28	107.6
N3—C2—C1	119.7 (5)	C35—C28—H28	107.6
C3—C2—C1	117.0 (5)	C32—O6—H6	134.0
C4—C3—C2	122.4 (6)	C32—O6—H6'	118.5
C4—C3—Br1	119.0 (5)	H6—O6—H6'	20.8
C2—C3—Br1	118.5 (5)	C34—C29—C30	120.7 (6)
C5—C4—C3	118.5 (6)	C34—C29—N5	126.4 (6)
C5—C4—H4	120.8	C30—C29—N5	112.1 (6)
C3—C4—H4	120.8	C34—C29—H29A	93.0
C6—C5—C4	121.6 (6)	C30—C29—H29A	93.0
C6—C5—Br2	119.5 (6)	N5—C29—H29A	93.0
C4—C5—Br2	118.8 (5)	C29—C30—C31	118.7 (7)
C5—C6—C1	120.8 (6)	C29—C30—H30A	107.6
C5—C6—H6B	119.6	C31—C30—H30A	107.6
C1—C6—H6B	119.6	C29—C30—H30B	107.6
N2—C7—C1	114.2 (4)	C31—C30—H30B	107.6
N2—C7—H7A	108.7	H30A—C30—H30B	107.1
C1—C7—H7A	108.7	C30—C31—C32	117.0 (8)
N2—C7—H7B	108.7	C30—C31—H31A	108.0
C1—C7—H7B	108.7	C32—C31—H31A	108.1
H7A—C7—H7B	107.6	C30—C31—H31B	108.0
N3—C8—N2	111.8 (4)	C32—C31—H31B	108.0
N3—C8—C15	113.2 (4)	H31A—C31—H31B	107.3
N2—C8—C15	110.3 (4)	O6—C32—C31	115.5 (14)
N3—C8—H8	107.1	O6—C32—C33	109.5 (12)
N2—C8—H8	107.1	C31—C32—C33	115.2 (9)
C15—C8—H8	107.1	O6—C32—H32A	105.1
N2—C9—C14	113.4 (5)	C31—C32—H32A	105.1
N2—C9—C10	108.7 (5)	C33—C32—H32A	105.1
C14—C9—C10	109.1 (5)	C34—C33—C32	117.0 (8)
N2—C9—H9	108.5	C34—C33—H33A	108.1
C14—C9—H9	108.5	C32—C33—H33A	108.1
C10—C9—H9	108.5	C34—C33—H33B	108.1
C9—C10—C11	111.9 (6)	C32—C33—H33B	108.1
C9—C10—H10A	109.2	H33A—C33—H33B	107.3
C11—C10—H10A	109.2	C29—C34—C33	118.0 (7)
C9—C10—H10B	109.2	C29—C34—H34A	107.8
C11—C10—H10B	109.2	C33—C34—H34A	107.8
H10A—C10—H10B	107.9	C29—C34—H34B	107.8
C12—C11—C10	110.9 (6)	C33—C34—H34B	107.8
C12—C11—H11A	109.5	H34A—C34—H34B	107.1
C10—C11—H11A	109.5	C32'—O6'—H6	118.2
C12—C11—H11B	109.5	C32'—O6'—H6'	116.1
C10—C11—H11B	109.5	H6—O6'—H6'	32.6
H11A—C11—H11B	108.1	C31'—C30'—H30C	108.4
C11—C12—O3	111.2 (6)	C31'—C30'—H30D	108.4
C11—C12—C13	111.6 (6)	H30C—C30'—H30D	107.5
O3—C12—C13	108.1 (5)	C32'—C31'—C30'	111.1 (7)
C11—C12—H12	108.6	C32'—C31'—H31C	109.4
O3—C12—H12	108.6	C30'—C31'—H31C	109.4
C13—C12—H12	108.6	C32'—C31'—H31D	109.4
C12—C13—C14	110.3 (5)	C30'—C31'—H31D	109.4
C12—C13—H13A	109.6	H31C—C31'—H31D	108.0
C14—C13—H13A	109.6	O6'—C32'—C33'	111.3 (9)
C12—C13—H13B	109.6	O6'—C32'—C31'	107.2 (9)
C14—C13—H13B	109.6	C33'—C32'—C31'	110.1 (7)
H13A—C13—H13B	108.1	O6'—C32'—H32B	109.4
C9—C14—C13	111.8 (5)	C33'—C32'—H32B	109.4
C9—C14—H14A	109.3	C31'—C32'—H32B	109.4
C13—C14—H14A	109.3	C32'—C33'—C34'	110.9 (7)
C9—C14—H14B	109.3	C32'—C33'—H33C	109.5
C13—C14—H14B	109.3	C34'—C33'—H33C	109.5
H14A—C14—H14B	107.9	C32'—C33'—H33D	109.5
C16—C15—C20	116.8 (5)	C34'—C33'—H33D	109.5
C16—C15—C8	122.2 (5)	H33C—C33'—H33D	108.1
C20—C15—C8	120.8 (5)	C33'—C34'—H34C	108.7
C15—C16—C17	120.9 (5)	C33'—C34'—H34D	108.7
C15—C16—H16	119.5	H34C—C34'—H34D	107.6
C17—C16—H16	119.5	C36—C35—C40	116.3 (5)
C16—C17—C18	121.8 (5)	C36—C35—C28	122.9 (5)
C16—C17—N1	119.2 (5)	C40—C35—C28	120.9 (4)
C18—C17—N1	119.0 (5)	C37—C36—C35	120.2 (5)
C19—C18—C17	117.6 (5)	C37—C36—H36	119.9
C19—C18—H18	121.2	C35—C36—H36	119.9
C17—C18—H18	121.2	C38—C37—C36	122.7 (5)
C20—C19—C18	120.7 (5)	C38—C37—N4	119.3 (6)
C20—C19—H19	119.7	C36—C37—N4	118.0 (6)
C18—C19—H19	119.7	C39—C38—C37	117.7 (6)
C19—C20—C15	122.1 (5)	C39—C38—H38	121.1
C19—C20—Cl1	117.5 (4)	C37—C38—H38	121.1
C15—C20—Cl1	120.4 (4)	C38—C39—C40	120.7 (5)
C26—C21—C22	121.0 (5)	C38—C39—H39	119.7
C26—C21—C27	122.4 (5)	C40—C39—H39	119.7
C22—C21—C27	116.7 (5)	C39—C40—C35	122.4 (5)
N6—C22—C21	120.0 (5)	C39—C40—Cl2	116.8 (4)
N6—C22—C23	122.3 (5)	C35—C40—Cl2	120.8 (4)
C21—C22—C23	117.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O4ⁱ	0.86	2.33	2.942 (7)	129
O3—H3···O6′ⁱⁱ	0.84	1.89	2.713 (12)	166
O6—H6···O3ⁱⁱⁱ	0.84	2.04	2.877 (17)	179
O6′—H6′···O3ⁱⁱⁱ	0.84	1.85	2.694 (10)	179

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀Br₂ClN₃O₃
M_r	545.66
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.2614 (13), 13.1418 (17), 16.931 (2)
α, β, γ (°)	83.764 (2), 73.309 (2), 84.750 (2)
V (Å³)	2169.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.89
Crystal size (mm)	0.30 × 0.28 × 0.28

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.389, 0.409
No. of measured, independent and observed [I > 2σ(I)] reflections	11972, 8470, 4874
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.622

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.154, 1.02
No. of reflections	8470
No. of parameters	578
No. of restraints	122
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.56, −1.07

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
N3—H3N···O4ⁱ	0.86	2.33	2.942 (7)	128.9
O3—H3···O6'ⁱⁱ	0.84	1.89	2.713 (12)	166.0
O6—H6···O3ⁱⁱⁱ	0.84	2.04	2.877 (17)	179.4
O6'—H6'···O3ⁱⁱⁱ	0.84	1.85	2.694 (10)	178.7

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) x−1, y, z.

Acknowledgements

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

References

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Volume 66| Part 5| May 2010| Pages o1205-o1206

https://doi.org/10.1107/S1600536810015023

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

4-[6,8-Di­bromo-2-(2-chloro-5-nitro­phen­yl)-1,2,3,4-tetra­hydro­quinazolin-3-yl]cyclo­hexa­nol

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-[6,8-Dibromo-2-(2-chloro-5-nitrophenyl)-1,2,3,4-tetrahydroquinazolin-3-yl]cyclohexanol