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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 5| May 2010| Pages o1205-o1206

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

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[Felix, F. S., Brett, C. M. A. & Angnes, L. (2008). Talanta, 76, 128-133.]); Gaida et al. (2005[Gaida, W., Klinder, K., Arndt, K. & Weiser, T. (2005). Neuropharmacology, 49, 1220-1227.]); Lee et al. (2004[Lee, H. J., Joung, S. K., Kim, Y. G., Yoo, J.-Y. & Han, S. B. (2004). Pharm. Res. 49, 93-98.]). For a related structure, see: Wang et al. (2009[Wang, Z.-G., Wang, R., Zhang, Y., Zhi, F. & Yang, Y.-L. (2009). Acta Cryst. E65, o550.]). For standard bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C20H20Br2ClN3O3

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.389, Tmax = 0.409

  • 11972 measured reflections

  • 8470 independent reflections

  • 4874 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 1.56 e Å−3

  • Δρmin = −1.07 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

H atoms were included in calulated positions with, with C–H = 0.93–0.98 Å, N-H = 0.86Å and O-H = 0.84 with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(O). The C29-C34 cyclohexyl ring is disordered over two distinct sites, with refined occupancies of 0.657 (12) and 0.343 (12). Bond length restraints were applied to the disorder model using the SADI commmand in SHELXL (Sheldrick, 2008).

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
[Figure 1] 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
C20H20Br2ClN3O3Z = 4
Mr = 545.66F(000) = 1088
Triclinic, P1Dx = 1.670 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.2614 (13) ÅCell parameters from 2646 reflections
b = 13.1418 (17) Åθ = 2.5–24.5°
c = 16.931 (2) ŵ = 3.89 mm1
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 tube4874 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scansθmax = 26.2°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 127
Tmin = 0.389, Tmax = 0.409k = 1516
11972 measured reflectionsl = 2120
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0631P)2 + 2.7275P]
where P = (Fo2 + 2Fc2)/3
8470 reflections(Δ/σ)max = 0.001
578 parametersΔρmax = 1.56 e Å3
122 restraintsΔρmin = 1.07 e Å3
Crystal data top
C20H20Br2ClN3O3γ = 84.750 (2)°
Mr = 545.66V = 2169.8 (5) Å3
Triclinic, P1Z = 4
a = 10.2614 (13) ÅMo Kα radiation
b = 13.1418 (17) ŵ = 3.89 mm1
c = 16.931 (2) ÅT = 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)
Tmin = 0.389, Tmax = 0.409Rint = 0.022
11972 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055122 restraints
wR(F2) = 0.154H-atom parameters constrained
S = 1.02Δρmax = 1.56 e Å3
8470 reflectionsΔρmin = 1.07 e Å3
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
xyzUiso*/UeqOcc. (<1)
Br10.39058 (9)0.05133 (6)0.42693 (4)0.0888 (3)
Br20.06018 (7)0.08773 (7)0.30819 (7)0.1156 (4)
Br30.65212 (7)0.61194 (6)0.35191 (6)0.0919 (3)
Br40.59092 (6)0.18627 (5)0.36046 (5)0.0747 (2)
Cl10.87128 (15)0.09542 (13)0.01005 (10)0.0700 (4)
Cl20.17164 (14)0.27481 (12)0.47738 (9)0.0628 (4)
O10.4691 (6)0.4725 (4)0.1616 (4)0.133 (3)
O20.3509 (5)0.3554 (4)0.2309 (4)0.0953 (16)
O30.8184 (5)0.4244 (3)0.0419 (3)0.0816 (14)
H30.85610.45730.00300.122*
O40.2375 (7)0.1609 (5)0.7120 (4)0.119 (2)
O50.0491 (7)0.1570 (6)0.8042 (4)0.145 (3)
N10.4516 (6)0.3856 (4)0.1802 (4)0.0731 (15)
N20.5854 (4)0.0384 (3)0.0978 (3)0.0435 (10)
N30.5434 (4)0.0321 (3)0.2395 (2)0.0472 (11)
H3N0.57930.04640.27970.057*
N40.1168 (8)0.1719 (5)0.7331 (4)0.0849 (18)
N50.1019 (4)0.3814 (3)0.4122 (2)0.0425 (10)
N60.2870 (4)0.2572 (3)0.4237 (3)0.0557 (12)
H6N0.32090.19490.42510.067*
C10.3494 (5)0.0295 (4)0.1906 (3)0.0469 (13)
C20.4071 (6)0.0031 (4)0.2565 (3)0.0482 (13)
C30.3189 (7)0.0040 (4)0.3370 (3)0.0579 (15)
C40.1815 (7)0.0235 (4)0.3527 (4)0.0704 (19)
H40.12510.02170.40670.085*
C50.1303 (6)0.0533 (5)0.2873 (5)0.0723 (19)
C60.2116 (6)0.0578 (4)0.2078 (4)0.0598 (16)
H6B0.17400.08010.16460.072*
C70.4418 (5)0.0291 (4)0.1042 (3)0.0483 (13)
H7A0.43330.03420.08190.058*
H7B0.41190.08540.07020.058*
C80.6281 (5)0.0394 (4)0.1557 (3)0.0407 (12)
H80.72060.02540.15490.049*
C90.6166 (6)0.1452 (4)0.1032 (4)0.0569 (15)
H90.54230.17580.14620.068*
C100.6231 (9)0.2061 (5)0.0216 (5)0.097 (3)
H10A0.53570.20640.01020.116*
H10B0.69120.17310.02210.116*
C110.6590 (10)0.3179 (6)0.0215 (6)0.111 (3)
H11A0.66490.35390.03240.133*
H11B0.58730.35280.06220.133*
C120.7856 (8)0.3205 (5)0.0402 (4)0.078 (2)
H120.85770.28790.00270.093*
C130.7829 (8)0.2642 (5)0.1224 (5)0.086 (2)
H13A0.71520.29780.16590.103*
H13B0.87110.26560.13250.103*
C140.7484 (7)0.1518 (5)0.1241 (4)0.0737 (19)
H14A0.82160.11650.08470.088*
H14B0.74170.11760.17870.088*
C150.6360 (5)0.1458 (4)0.1260 (3)0.0410 (12)
C160.5412 (5)0.2159 (4)0.1637 (3)0.0465 (13)
H160.46640.19730.20690.056*
C170.5551 (6)0.3135 (4)0.1386 (3)0.0511 (13)
C180.6655 (6)0.3457 (5)0.0763 (4)0.0662 (17)
H180.67520.41230.06070.079*
C190.7607 (6)0.2758 (5)0.0380 (4)0.0614 (16)
H190.83610.29500.00450.074*
C200.7458 (5)0.1784 (4)0.0618 (3)0.0487 (13)
C210.3193 (5)0.4363 (4)0.4205 (3)0.0445 (12)
C220.3731 (5)0.3365 (4)0.4085 (3)0.0443 (12)
C230.5137 (5)0.3210 (4)0.3792 (3)0.0481 (13)
C240.5984 (6)0.4014 (5)0.3633 (3)0.0586 (16)
H240.69250.38950.34400.070*
C250.5415 (6)0.4989 (5)0.3765 (4)0.0595 (15)
C260.4024 (6)0.5159 (4)0.4057 (3)0.0539 (14)
H260.36470.58200.41550.065*
C270.1651 (5)0.4519 (4)0.4489 (3)0.0449 (12)
H27A0.13380.44070.50870.054*
H27B0.13780.52200.43310.054*
C280.1395 (5)0.2766 (4)0.4373 (3)0.0463 (13)
H280.11100.23190.40340.056*
O60.0678 (19)0.4493 (13)0.0811 (8)0.057 (4)0.343 (12)
H60.00510.44250.06960.085*0.343 (12)
C290.1191 (7)0.4085 (5)0.3235 (3)0.079 (2)0.343 (12)
H29A0.17920.46340.32100.095*0.343 (12)
C300.0096 (19)0.4808 (16)0.3083 (8)0.052 (8)0.343 (12)
H30A0.02730.54810.31970.062*0.343 (12)
H30B0.07480.46160.34850.062*0.343 (12)
C310.0137 (17)0.4906 (19)0.2262 (8)0.067 (6)0.343 (12)
H31A0.04120.56170.21370.080*0.343 (12)
H31B0.08960.45020.22900.080*0.343 (12)
C320.1012 (18)0.4595 (13)0.1567 (7)0.065 (6)0.343 (12)
H32A0.16180.51620.14370.078*0.343 (12)
C330.1854 (18)0.3684 (13)0.1758 (7)0.053 (6)0.343 (12)
H33A0.13980.30800.17310.063*0.343 (12)
H33B0.27130.36710.13270.063*0.343 (12)
C340.2156 (15)0.3599 (13)0.2562 (6)0.057 (5)0.343 (12)
H34A0.22570.28760.27370.068*0.343 (12)
H34B0.30320.38810.24760.068*0.343 (12)
O6'0.0198 (12)0.4810 (10)0.0975 (6)0.095 (4)0.657 (12)
H6'0.04360.46420.08020.142*0.657 (12)
C29'0.1191 (7)0.4085 (5)0.3235 (3)0.079 (2)0.657 (12)
H29B0.21380.42770.30260.095*0.657 (12)
C30'0.0385 (12)0.5058 (7)0.3093 (5)0.049 (3)0.657 (12)
H30C0.07380.56100.32920.059*0.657 (12)
H30D0.05520.49920.34250.059*0.657 (12)
C31'0.0389 (12)0.5356 (7)0.2214 (5)0.067 (3)0.657 (12)
H31C0.03140.58970.21980.081*0.657 (12)
H31D0.12620.56190.19080.081*0.657 (12)
C32'0.0143 (13)0.4461 (8)0.1814 (6)0.081 (4)0.657 (12)
H32B0.07640.42240.21010.098*0.657 (12)
C33'0.1193 (15)0.3608 (7)0.1855 (5)0.077 (4)0.657 (12)
H33C0.20910.38390.15650.092*0.657 (12)
H33D0.10370.30370.15830.092*0.657 (12)
C34'0.1142 (13)0.3259 (6)0.2735 (5)0.072 (3)0.657 (12)
H34C0.03090.29120.29890.087*0.657 (12)
H34D0.19020.27640.27390.087*0.657 (12)
C350.0602 (5)0.2507 (4)0.5269 (3)0.0420 (12)
C360.1226 (6)0.2241 (4)0.5892 (4)0.0519 (14)
H360.21720.22050.57690.062*
C370.0451 (7)0.2028 (4)0.6695 (4)0.0570 (15)
C380.0942 (7)0.2086 (4)0.6919 (4)0.0617 (16)
H380.14440.19640.74690.074*
C390.1569 (6)0.2328 (4)0.6310 (3)0.0516 (14)
H390.25150.23600.64420.062*
C400.0820 (5)0.2523 (4)0.5505 (3)0.0435 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1211 (7)0.0938 (6)0.0491 (4)0.0380 (5)0.0139 (4)0.0028 (3)
Br20.0488 (4)0.0931 (6)0.1853 (10)0.0068 (4)0.0052 (5)0.0404 (6)
Br30.0649 (4)0.0829 (5)0.1281 (7)0.0302 (4)0.0261 (4)0.0094 (5)
Br40.0500 (4)0.0687 (4)0.0959 (5)0.0196 (3)0.0086 (3)0.0173 (4)
Cl10.0529 (9)0.0799 (11)0.0661 (10)0.0119 (8)0.0041 (8)0.0084 (8)
Cl20.0496 (8)0.0840 (11)0.0619 (9)0.0129 (7)0.0264 (7)0.0010 (8)
O10.120 (5)0.060 (3)0.193 (7)0.028 (3)0.019 (4)0.048 (4)
O20.073 (3)0.074 (3)0.120 (4)0.024 (3)0.013 (3)0.020 (3)
O30.106 (4)0.048 (3)0.083 (3)0.029 (2)0.010 (3)0.002 (2)
O40.096 (4)0.143 (5)0.134 (5)0.020 (4)0.076 (4)0.052 (4)
O50.147 (6)0.219 (8)0.072 (4)0.013 (5)0.056 (4)0.040 (4)
N10.073 (4)0.048 (3)0.094 (4)0.014 (3)0.011 (3)0.012 (3)
N20.046 (2)0.038 (2)0.048 (3)0.0040 (19)0.015 (2)0.004 (2)
N30.055 (3)0.051 (3)0.037 (2)0.004 (2)0.017 (2)0.006 (2)
N40.099 (5)0.081 (4)0.085 (5)0.012 (4)0.052 (4)0.022 (3)
N50.040 (2)0.045 (3)0.042 (2)0.0008 (19)0.0101 (19)0.0040 (19)
N60.042 (3)0.038 (3)0.079 (3)0.006 (2)0.005 (2)0.010 (2)
C10.047 (3)0.036 (3)0.057 (3)0.001 (2)0.014 (3)0.009 (3)
C20.059 (3)0.031 (3)0.053 (3)0.008 (2)0.008 (3)0.010 (2)
C30.076 (4)0.040 (3)0.050 (3)0.014 (3)0.002 (3)0.006 (3)
C40.068 (4)0.050 (4)0.072 (5)0.015 (3)0.023 (4)0.021 (3)
C50.049 (4)0.055 (4)0.101 (6)0.001 (3)0.003 (4)0.022 (4)
C60.052 (3)0.044 (3)0.084 (5)0.002 (3)0.015 (3)0.016 (3)
C70.049 (3)0.043 (3)0.056 (3)0.002 (2)0.021 (3)0.004 (3)
C80.040 (3)0.040 (3)0.044 (3)0.001 (2)0.016 (2)0.003 (2)
C90.063 (4)0.048 (3)0.063 (4)0.005 (3)0.023 (3)0.001 (3)
C100.142 (7)0.068 (5)0.106 (6)0.036 (5)0.080 (6)0.023 (4)
C110.148 (8)0.072 (5)0.141 (8)0.035 (5)0.094 (7)0.039 (5)
C120.099 (5)0.060 (4)0.070 (4)0.031 (4)0.012 (4)0.005 (3)
C130.110 (6)0.073 (5)0.088 (5)0.035 (4)0.045 (5)0.004 (4)
C140.079 (5)0.067 (4)0.082 (5)0.022 (4)0.037 (4)0.014 (4)
C150.043 (3)0.041 (3)0.040 (3)0.001 (2)0.014 (2)0.001 (2)
C160.047 (3)0.044 (3)0.048 (3)0.001 (2)0.013 (3)0.005 (2)
C170.052 (3)0.041 (3)0.059 (4)0.002 (3)0.014 (3)0.006 (3)
C180.070 (4)0.047 (4)0.078 (4)0.007 (3)0.012 (4)0.021 (3)
C190.056 (4)0.065 (4)0.052 (4)0.003 (3)0.004 (3)0.018 (3)
C200.043 (3)0.051 (3)0.048 (3)0.000 (2)0.008 (3)0.004 (3)
C210.044 (3)0.042 (3)0.046 (3)0.002 (2)0.014 (2)0.000 (2)
C220.045 (3)0.042 (3)0.044 (3)0.003 (2)0.013 (2)0.001 (2)
C230.041 (3)0.056 (3)0.044 (3)0.004 (3)0.010 (2)0.003 (3)
C240.036 (3)0.081 (5)0.058 (4)0.001 (3)0.016 (3)0.003 (3)
C250.049 (3)0.062 (4)0.066 (4)0.012 (3)0.016 (3)0.004 (3)
C260.053 (3)0.050 (3)0.058 (4)0.005 (3)0.014 (3)0.003 (3)
C270.041 (3)0.036 (3)0.052 (3)0.001 (2)0.006 (3)0.004 (2)
C280.042 (3)0.043 (3)0.054 (3)0.002 (2)0.013 (3)0.007 (3)
O60.080 (8)0.053 (7)0.038 (7)0.013 (6)0.021 (6)0.010 (5)
C290.095 (5)0.086 (5)0.056 (4)0.039 (4)0.028 (4)0.021 (4)
C300.055 (10)0.053 (10)0.045 (10)0.000 (8)0.011 (7)0.007 (7)
C310.072 (10)0.074 (10)0.056 (9)0.013 (8)0.027 (8)0.002 (8)
C320.099 (18)0.061 (13)0.038 (11)0.000 (12)0.025 (12)0.005 (9)
C330.040 (11)0.080 (14)0.038 (10)0.002 (9)0.010 (8)0.009 (9)
C340.045 (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)
C350.042 (3)0.036 (3)0.050 (3)0.002 (2)0.017 (3)0.009 (2)
C360.046 (3)0.041 (3)0.069 (4)0.003 (2)0.022 (3)0.001 (3)
C370.075 (4)0.046 (3)0.058 (4)0.002 (3)0.036 (3)0.007 (3)
C380.075 (4)0.050 (4)0.055 (4)0.005 (3)0.013 (3)0.004 (3)
C390.049 (3)0.054 (3)0.050 (3)0.002 (3)0.014 (3)0.000 (3)
C400.044 (3)0.040 (3)0.051 (3)0.001 (2)0.020 (3)0.005 (2)
Geometric parameters (Å, º) top
Br1—C31.897 (6)C18—H180.9300
Br2—C51.904 (6)C19—C201.365 (8)
Br3—C251.890 (6)C19—H190.9300
Br4—C231.893 (5)C21—C261.367 (7)
Cl1—C201.737 (5)C21—C221.387 (7)
Cl2—C401.729 (5)C21—C271.517 (7)
O1—N11.201 (6)C22—C231.388 (7)
O2—N11.204 (7)C23—C241.384 (8)
O3—C121.441 (7)C24—C251.373 (8)
O3—H30.8401C24—H240.9300
O4—N41.186 (8)C25—C261.375 (8)
O5—N41.210 (8)C26—H260.9300
N1—C171.460 (7)C27—H27A0.9700
N2—C71.461 (6)C27—H27B0.9700
N2—C81.464 (6)C28—C351.519 (7)
N2—C91.487 (7)C28—H280.9800
N3—C21.371 (7)O6—C321.439 (10)
N3—C81.444 (6)O6—H60.8401
N3—H3N0.8600O6—H6'1.1466
N4—C371.472 (8)C29—C341.442 (8)
N5—C281.448 (6)C29—C301.466 (8)
N5—C271.460 (6)C29—H29A0.9800
N5—C291.470 (7)C30—C311.468 (9)
N6—C221.383 (6)C30—H30A0.9700
N6—C281.467 (6)C30—H30B0.9700
N6—H6N0.8600C31—C321.469 (9)
C1—C61.383 (7)C31—H31A0.9700
C1—C21.416 (7)C31—H31B0.9700
C1—C71.499 (7)C32—C331.474 (9)
C2—C31.403 (8)C32—H32A0.9800
C3—C41.379 (9)C33—C341.470 (9)
C4—C51.364 (9)C33—H33A0.9700
C4—H40.9300C33—H33B0.9700
C5—C61.363 (9)C34—H34A0.9700
C6—H6B0.9300C34—H34B0.9700
C7—H7A0.9700O6'—C32'1.432 (12)
C7—H7B0.9700O6'—H60.8290
C8—C151.525 (7)O6'—H6'0.8401
C8—H80.9800C30'—C31'1.496 (7)
C9—C141.505 (8)C30'—H30C0.9700
C9—C101.507 (8)C30'—H30D0.9700
C9—H90.9800C31'—C32'1.494 (7)
C10—C111.548 (9)C31'—H31C0.9700
C10—H10A0.9700C31'—H31D0.9700
C10—H10B0.9700C32'—C33'1.492 (8)
C11—C121.427 (10)C32'—H32B0.9800
C11—H11A0.9700C33'—C34'1.497 (7)
C11—H11B0.9700C33'—H33C0.9700
C12—C131.497 (9)C33'—H33D0.9700
C12—H120.9800C34'—H34C0.9700
C13—C141.545 (9)C34'—H34D0.9700
C13—H13A0.9700C35—C361.382 (7)
C13—H13B0.9700C35—C401.397 (7)
C14—H14A0.9700C36—C371.377 (8)
C14—H14B0.9700C36—H360.9300
C15—C161.372 (7)C37—C381.367 (8)
C15—C201.394 (7)C38—C391.360 (8)
C16—C171.376 (7)C38—H380.9300
C16—H160.9300C39—C401.369 (7)
C17—C181.378 (8)C39—H390.9300
C18—C191.375 (8)
C12—O3—H3118.6C24—C23—C22121.7 (5)
O1—N1—O2122.5 (6)C24—C23—Br4119.4 (4)
O1—N1—C17118.7 (6)C22—C23—Br4118.9 (4)
O2—N1—C17118.8 (5)C25—C24—C23119.0 (5)
C7—N2—C8109.3 (4)C25—C24—H24120.5
C7—N2—C9112.8 (4)C23—C24—H24120.5
C8—N2—C9115.5 (4)C24—C25—C26120.2 (5)
C2—N3—C8121.6 (4)C24—C25—Br3120.6 (4)
C2—N3—H3N119.2C26—C25—Br3119.1 (5)
C8—N3—H3N119.2C21—C26—C25120.5 (5)
O4—N4—O5123.2 (7)C21—C26—H26119.8
O4—N4—C37118.6 (7)C25—C26—H26119.8
O5—N4—C37118.1 (7)N5—C27—C21110.9 (4)
C28—N5—C27109.7 (4)N5—C27—H27A109.5
C28—N5—C29117.3 (4)C21—C27—H27A109.5
C27—N5—C29112.7 (4)N5—C27—H27B109.5
C22—N6—C28121.7 (4)C21—C27—H27B109.5
C22—N6—H6N119.2H27A—C27—H27B108.1
C28—N6—H6N119.2N5—C28—N6112.7 (4)
C6—C1—C2119.6 (5)N5—C28—C35109.0 (4)
C6—C1—C7122.8 (5)N6—C28—C35112.2 (4)
C2—C1—C7117.6 (5)N5—C28—H28107.6
N3—C2—C3123.3 (5)N6—C28—H28107.6
N3—C2—C1119.7 (5)C35—C28—H28107.6
C3—C2—C1117.0 (5)C32—O6—H6134.0
C4—C3—C2122.4 (6)C32—O6—H6'118.5
C4—C3—Br1119.0 (5)H6—O6—H6'20.8
C2—C3—Br1118.5 (5)C34—C29—C30120.7 (6)
C5—C4—C3118.5 (6)C34—C29—N5126.4 (6)
C5—C4—H4120.8C30—C29—N5112.1 (6)
C3—C4—H4120.8C34—C29—H29A93.0
C6—C5—C4121.6 (6)C30—C29—H29A93.0
C6—C5—Br2119.5 (6)N5—C29—H29A93.0
C4—C5—Br2118.8 (5)C29—C30—C31118.7 (7)
C5—C6—C1120.8 (6)C29—C30—H30A107.6
C5—C6—H6B119.6C31—C30—H30A107.6
C1—C6—H6B119.6C29—C30—H30B107.6
N2—C7—C1114.2 (4)C31—C30—H30B107.6
N2—C7—H7A108.7H30A—C30—H30B107.1
C1—C7—H7A108.7C30—C31—C32117.0 (8)
N2—C7—H7B108.7C30—C31—H31A108.0
C1—C7—H7B108.7C32—C31—H31A108.1
H7A—C7—H7B107.6C30—C31—H31B108.0
N3—C8—N2111.8 (4)C32—C31—H31B108.0
N3—C8—C15113.2 (4)H31A—C31—H31B107.3
N2—C8—C15110.3 (4)O6—C32—C31115.5 (14)
N3—C8—H8107.1O6—C32—C33109.5 (12)
N2—C8—H8107.1C31—C32—C33115.2 (9)
C15—C8—H8107.1O6—C32—H32A105.1
N2—C9—C14113.4 (5)C31—C32—H32A105.1
N2—C9—C10108.7 (5)C33—C32—H32A105.1
C14—C9—C10109.1 (5)C34—C33—C32117.0 (8)
N2—C9—H9108.5C34—C33—H33A108.1
C14—C9—H9108.5C32—C33—H33A108.1
C10—C9—H9108.5C34—C33—H33B108.1
C9—C10—C11111.9 (6)C32—C33—H33B108.1
C9—C10—H10A109.2H33A—C33—H33B107.3
C11—C10—H10A109.2C29—C34—C33118.0 (7)
C9—C10—H10B109.2C29—C34—H34A107.8
C11—C10—H10B109.2C33—C34—H34A107.8
H10A—C10—H10B107.9C29—C34—H34B107.8
C12—C11—C10110.9 (6)C33—C34—H34B107.8
C12—C11—H11A109.5H34A—C34—H34B107.1
C10—C11—H11A109.5C32'—O6'—H6118.2
C12—C11—H11B109.5C32'—O6'—H6'116.1
C10—C11—H11B109.5H6—O6'—H6'32.6
H11A—C11—H11B108.1C31'—C30'—H30C108.4
C11—C12—O3111.2 (6)C31'—C30'—H30D108.4
C11—C12—C13111.6 (6)H30C—C30'—H30D107.5
O3—C12—C13108.1 (5)C32'—C31'—C30'111.1 (7)
C11—C12—H12108.6C32'—C31'—H31C109.4
O3—C12—H12108.6C30'—C31'—H31C109.4
C13—C12—H12108.6C32'—C31'—H31D109.4
C12—C13—C14110.3 (5)C30'—C31'—H31D109.4
C12—C13—H13A109.6H31C—C31'—H31D108.0
C14—C13—H13A109.6O6'—C32'—C33'111.3 (9)
C12—C13—H13B109.6O6'—C32'—C31'107.2 (9)
C14—C13—H13B109.6C33'—C32'—C31'110.1 (7)
H13A—C13—H13B108.1O6'—C32'—H32B109.4
C9—C14—C13111.8 (5)C33'—C32'—H32B109.4
C9—C14—H14A109.3C31'—C32'—H32B109.4
C13—C14—H14A109.3C32'—C33'—C34'110.9 (7)
C9—C14—H14B109.3C32'—C33'—H33C109.5
C13—C14—H14B109.3C34'—C33'—H33C109.5
H14A—C14—H14B107.9C32'—C33'—H33D109.5
C16—C15—C20116.8 (5)C34'—C33'—H33D109.5
C16—C15—C8122.2 (5)H33C—C33'—H33D108.1
C20—C15—C8120.8 (5)C33'—C34'—H34C108.7
C15—C16—C17120.9 (5)C33'—C34'—H34D108.7
C15—C16—H16119.5H34C—C34'—H34D107.6
C17—C16—H16119.5C36—C35—C40116.3 (5)
C16—C17—C18121.8 (5)C36—C35—C28122.9 (5)
C16—C17—N1119.2 (5)C40—C35—C28120.9 (4)
C18—C17—N1119.0 (5)C37—C36—C35120.2 (5)
C19—C18—C17117.6 (5)C37—C36—H36119.9
C19—C18—H18121.2C35—C36—H36119.9
C17—C18—H18121.2C38—C37—C36122.7 (5)
C20—C19—C18120.7 (5)C38—C37—N4119.3 (6)
C20—C19—H19119.7C36—C37—N4118.0 (6)
C18—C19—H19119.7C39—C38—C37117.7 (6)
C19—C20—C15122.1 (5)C39—C38—H38121.1
C19—C20—Cl1117.5 (4)C37—C38—H38121.1
C15—C20—Cl1120.4 (4)C38—C39—C40120.7 (5)
C26—C21—C22121.0 (5)C38—C39—H39119.7
C26—C21—C27122.4 (5)C40—C39—H39119.7
C22—C21—C27116.7 (5)C39—C40—C35122.4 (5)
N6—C22—C21120.0 (5)C39—C40—Cl2116.8 (4)
N6—C22—C23122.3 (5)C35—C40—Cl2120.8 (4)
C21—C22—C23117.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O4i0.862.332.942 (7)129
O3—H3···O6ii0.841.892.713 (12)166
O6—H6···O3iii0.842.042.877 (17)179
O6—H6···O3iii0.841.852.694 (10)179
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z; (iii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC20H20Br2ClN3O3
Mr545.66
Crystal system, space groupTriclinic, 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)
V3)2169.8 (5)
Z4
Radiation typeMo Kα
µ (mm1)3.89
Crystal size (mm)0.30 × 0.28 × 0.28
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.389, 0.409
No. of measured, independent and
observed [I > 2σ(I)] reflections
11972, 8470, 4874
Rint0.022
(sin θ/λ)max1)0.622
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.154, 1.02
No. of reflections8470
No. of parameters578
No. of restraints122
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N3—H3N···O4i0.862.332.942 (7)128.9
O3—H3···O6'ii0.841.892.713 (12)166.0
O6—H6···O3iii0.842.042.877 (17)179.4
O6'—H6'···O3iii0.841.852.694 (10)178.7
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z; (iii) x1, y, z.
 

Acknowledgements

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

References

First citationAllen, 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
First citationBruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFelix, F. S., Brett, C. M. A. & Angnes, L. (2008). Talanta, 76, 128–133.  Web of Science CrossRef PubMed CAS
First citationGaida, W., Klinder, K., Arndt, K. & Weiser, T. (2005). Neuropharmacology, 49, 1220–1227.  Web of Science CrossRef PubMed CAS
First citationLee, 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
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWang, Z.-G., Wang, R., Zhang, Y., Zhi, F. & Yang, Y.-L. (2009). Acta Cryst. E65, o550.  Web of Science CSD CrossRef IUCr Journals

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ISSN: 2056-9890
Volume 66| Part 5| May 2010| Pages o1205-o1206
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