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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 4| April 2011| Pages o808-o809

2-[6,8-Di­bromo-3-(4-hy­dr­oxy­cyclo­hex­yl)-1,2,3,4-tetra­hydro­quinazolin-2-yl]phenol methanol 0.25-solvate

aDepartment of Respiratory Medicine, 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 Pharmacy, Third Affiliated Hospital of Soochow University, Changzhou 213003, People's Republic of China
*Correspondence e-mail: wangmingli09@163.com

(Received 23 February 2011; accepted 2 March 2011; online 9 March 2011)

The title compound, C20H22Br2N2O2·0.25CH4O, was synthesized by the condensation reaction of salicyl­aldehyde with 4-(2-amino-3,5-dibromo­benzyl­amino)­cyclo­hexa­nol in methanol. There are four independent main mol­ecules and two half-occupied methanol solvent mol­ecules in the asymmetric unit. The dihedral angles between the two benzene rings in the four mol­ecules are 87.8 (6), 86.6 (6), 89.3 (6) and 83.1 (6)°. Each mol­ecule features an intra­molecular O—H⋯N hydrogen bond and a short N—H⋯Br link. In the crystal components are linked by O—H⋯O hydrogen bonds.

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: 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 the structures of similar compounds, see: Wang et al. (2009[Wang, Z.-G., Wang, R., Zhang, Y., Zhi, F. & Yang, Y.-L. (2009). Acta Cryst. E65, o550.], 2010[Wang, Z.-G., Xia, Z.-L., Wang, R. & Wang, M.-L. (2010). Acta Cryst. E66, o1205-o1206.]). 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
  • C20H22Br2N2O2·0.25CH4O

  • Mr = 490.23

  • Triclinic, [P \overline 1]

  • a = 11.733 (2) Å

  • b = 16.831 (3) Å

  • c = 21.721 (4) Å

  • α = 94.69 (3)°

  • β = 96.88 (3)°

  • γ = 99.44 (3)°

  • V = 4178.4 (14) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 3.90 mm−1

  • T = 298 K

  • 0.23 × 0.23 × 0.20 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.468, Tmax = 0.509

  • 46008 measured reflections

  • 17573 independent reflections

  • 6508 reflections with I > 2σ(I)

  • Rint = 0.108

Refinement
  • R[F2 > 2σ(F2)] = 0.087

  • wR(F2) = 0.199

  • S = 0.95

  • 17573 reflections

  • 1001 parameters

  • 38 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.06 e Å−3

  • Δρmin = −0.78 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N4 0.82 1.93 2.643 (8) 145
N1—H1A⋯Br2 0.91 (8) 2.69 (7) 3.081 (7) 107 (6)
O2—H2⋯O9i 0.82 1.85 2.660 (15) 167
O3—H3⋯N2 0.82 1.93 2.661 (9) 148
N3—H3B⋯Br4 0.91 (8) 2.77 (8) 3.097 (7) 103 (5)
O4—H4⋯O6ii 0.82 2.13 2.721 (10) 129
O5—H5⋯N6 0.82 1.95 2.650 (9) 143
N5—H5B⋯Br5 0.90 (6) 2.77 (8) 3.110 (7) 104 (6)
O6—H6⋯O8iii 0.82 1.95 2.735 (9) 160
O7—H7⋯N8 0.85 (6) 1.99 (8) 2.717 (9) 142 (6)
N7—H7B⋯Br7 0.90 (6) 2.61 (8) 3.100 (7) 115 (6)
O8—H8⋯O2iv 0.84 (9) 1.90 (8) 2.713 (11) 162 (8)
O9—H9⋯O10v 0.82 2.18 2.94 (2) 156
Symmetry codes: (i) x+1, y, z-1; (ii) x, y, z-1; (iii) -x+1, -y, -z+2; (iv) x-1, y, z+1; (v) 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 [or 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol] is an expectorant agent which leads to bronchial secretion due to its mucolytic properties (Gaida et al., 2005; Lee et al., 2004). Recently, we reported the crystal structures of two derivatives of Ambroxol (Wang et al., 2009; Wang et al., 2010). In this paper, the crystal structure of the title compound, derived from the condensation reaction of salicylaldehyde with 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol in methanol, is reported.

There are four independent molecules and two methanol molecules in the asymmetric unit of the title compound, Fig. 1. The dihedral angles between the two benzene rings in the four molecules are 87.8 (6), 86.6 (6), 90.7 (6), and 96.9 (6)°, respectively. 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: Gaida et al. (2005); Lee et al. (2004). For the structures of similar compounds, see: Wang et al. (2009, 2010). For standard bond-length data, see: Allen et al. (1987).

Experimental top

Salicylaldehyde (1.0 mol, 122.1 mg) and 4-(2-amino-3,5-dibromobenzylamino)cyclohexanol (1.0 mmol, 378.1 mg) were dissolved in methanol (30 ml). The mixture was stirred at room temperature to give a clear colorless solution. Colourless blocks of the title compound were formed by gradual evaporation of the solvent for a few days at room temperature.

Refinement top

H1A, H3B, H5B, H7B, and H7 atoms were located from a difference Fourier map and refined isotropically, with N—H and O—H distances restrained to 0.90 (1) and 0.85 (1) Å, respectively. The other H atoms were included in calulated positions with, with C—H = 0.93–0.98 Å, and O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O and methyl C).

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.
2-[6,8-Dibromo-3-(4-hydroxycyclohexyl)-1,2,3,4-tetrahydroquinazolin-2-yl]phenol methanol 0.25-solvate top
Crystal data top
C20H22Br2N2O2·0.25CH4OZ = 8
Mr = 490.23F(000) = 1972
Triclinic, P1Dx = 1.559 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.733 (2) ÅCell parameters from 2369 reflections
b = 16.831 (3) Åθ = 2.5–24.3°
c = 21.721 (4) ŵ = 3.90 mm1
α = 94.69 (3)°T = 298 K
β = 96.88 (3)°Block, colorless
γ = 99.44 (3)°0.23 × 0.23 × 0.20 mm
V = 4178.4 (14) Å3
Data collection top
Bruker SMART CCD
diffractometer
17573 independent reflections
Radiation source: fine-focus sealed tube6508 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.108
ω scansθmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.468, Tmax = 0.509k = 2121
46008 measured reflectionsl = 2727
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)] = 0.087Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.199H atoms treated by a mixture of independent and constrained refinement
S = 0.95 w = 1/[σ2(Fo2) + (0.0601P)2]
where P = (Fo2 + 2Fc2)/3
17573 reflections(Δ/σ)max = 0.001
1001 parametersΔρmax = 1.06 e Å3
38 restraintsΔρmin = 0.78 e Å3
Crystal data top
C20H22Br2N2O2·0.25CH4Oγ = 99.44 (3)°
Mr = 490.23V = 4178.4 (14) Å3
Triclinic, P1Z = 8
a = 11.733 (2) ÅMo Kα radiation
b = 16.831 (3) ŵ = 3.90 mm1
c = 21.721 (4) ÅT = 298 K
α = 94.69 (3)°0.23 × 0.23 × 0.20 mm
β = 96.88 (3)°
Data collection top
Bruker SMART CCD
diffractometer
17573 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
6508 reflections with I > 2σ(I)
Tmin = 0.468, Tmax = 0.509Rint = 0.108
46008 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.08738 restraints
wR(F2) = 0.199H atoms treated by a mixture of independent and constrained refinement
S = 0.95Δρmax = 1.06 e Å3
17573 reflectionsΔρmin = 0.78 e Å3
1001 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)
Br10.50780 (11)0.54851 (6)0.41605 (5)0.0858 (4)
Br20.75088 (8)0.28881 (6)0.44920 (4)0.0564 (3)
Br31.02222 (11)0.55820 (6)0.42630 (5)0.0768 (4)
Br41.26724 (8)0.29701 (6)0.44757 (4)0.0573 (3)
Br50.73267 (9)0.40022 (6)0.68344 (5)0.0733 (3)
Br61.12176 (15)0.56107 (7)0.85040 (8)0.1393 (7)
Br70.22232 (9)0.41215 (6)0.68357 (5)0.0680 (3)
Br80.59680 (15)0.58398 (7)0.85557 (8)0.1367 (7)
O10.7323 (5)0.0798 (3)0.2677 (3)0.0541 (16)
H10.78050.10760.25040.081*
O21.1310 (8)0.2056 (5)0.0423 (4)0.109 (3)
H21.09540.23930.02750.164*
O30.2270 (5)0.0715 (4)0.2618 (3)0.0570 (17)
H30.27050.10410.24550.085*
O40.6491 (7)0.1764 (5)0.0424 (3)0.085 (2)
H40.70560.15420.03910.128*
O51.0710 (5)0.0754 (4)0.7097 (3)0.0603 (17)
H51.02950.08420.73640.090*
O60.7231 (6)0.0560 (4)0.9749 (3)0.075 (2)
H60.75170.01840.98830.113*
O70.5483 (6)0.0782 (4)0.7181 (3)0.0605 (17)
O80.2347 (6)0.0897 (4)0.9893 (3)0.073 (2)
N10.5676 (6)0.2056 (4)0.3396 (3)0.0406 (17)
N20.4082 (5)0.1867 (4)0.2547 (3)0.0368 (16)
N31.0712 (6)0.2146 (4)0.3426 (3)0.0405 (17)
N40.9067 (5)0.1991 (4)0.2622 (3)0.0369 (16)
N50.8385 (6)0.2493 (4)0.7178 (3)0.0430 (17)
N60.9564 (5)0.1679 (4)0.7749 (3)0.0341 (16)
N70.3360 (6)0.2657 (4)0.7195 (3)0.0466 (18)
N80.4575 (5)0.1926 (4)0.7824 (3)0.0393 (17)
C10.3768 (7)0.1178 (4)0.3488 (4)0.0338 (19)
C20.2633 (8)0.0780 (5)0.3238 (5)0.044 (2)
C30.1865 (8)0.0458 (4)0.3639 (5)0.052 (3)
H3A0.11200.01870.34800.063*
C40.2228 (9)0.0548 (5)0.4272 (5)0.054 (3)
H4A0.17130.03380.45360.065*
C50.3321 (9)0.0935 (5)0.4524 (4)0.055 (3)
H5A0.35520.09900.49520.066*
C60.4061 (7)0.1239 (5)0.4130 (4)0.047 (2)
H6A0.48050.15030.43010.057*
C70.4654 (7)0.1496 (5)0.3066 (4)0.037 (2)
H7A0.49380.10270.28810.044*
C80.4625 (7)0.3155 (4)0.3258 (3)0.036 (2)
C90.5528 (6)0.2828 (4)0.3580 (4)0.0330 (19)
C100.6297 (7)0.3326 (5)0.4049 (4)0.039 (2)
C110.6164 (8)0.4108 (5)0.4212 (4)0.052 (2)
H110.66790.44280.45300.062*
C120.5289 (8)0.4412 (5)0.3912 (4)0.049 (2)
C130.4520 (7)0.3943 (5)0.3435 (4)0.047 (2)
H130.39220.41630.32300.057*
C140.3733 (7)0.2620 (5)0.2785 (4)0.047 (2)
H14A0.30240.24810.29710.057*
H14B0.35530.29230.24370.057*
C150.4654 (8)0.1917 (5)0.1979 (4)0.047 (2)
H150.40970.21190.16840.056*
C160.4707 (8)0.1082 (5)0.1677 (4)0.056 (3)
H16A0.39420.07450.16310.067*
H16B0.52430.08320.19400.067*
C170.5117 (9)0.1145 (6)0.1033 (4)0.070 (3)
H17A0.52340.06150.08700.084*
H17B0.45050.13010.07520.084*
C180.6187 (9)0.1720 (6)0.1038 (5)0.070 (3)
H180.68090.15120.12830.084*
C190.6130 (8)0.2539 (5)0.1356 (4)0.062 (3)
H19A0.55930.27940.10970.074*
H19B0.68940.28770.14010.074*
C200.5737 (9)0.2483 (5)0.1989 (4)0.064 (3)
H20A0.63430.23170.22680.077*
H20B0.56340.30160.21550.077*
C210.8835 (7)0.1260 (4)0.3539 (4)0.037 (2)
C220.7711 (8)0.0852 (5)0.3305 (4)0.044 (2)
C230.6981 (8)0.0501 (5)0.3688 (5)0.052 (2)
H230.62450.02210.35200.063*
C240.7325 (9)0.0556 (5)0.4320 (5)0.057 (3)
H240.68130.03280.45790.068*
C250.8405 (9)0.0942 (5)0.4566 (4)0.055 (3)
H250.86410.09710.49930.066*
C260.9148 (8)0.1290 (5)0.4190 (4)0.048 (2)
H260.98870.15560.43670.057*
C270.9673 (7)0.1606 (4)0.3101 (4)0.036 (2)
H270.99400.11470.28910.043*
C280.9668 (7)0.3264 (4)0.3369 (4)0.038 (2)
C291.0599 (6)0.2932 (4)0.3632 (4)0.0319 (19)
C301.1402 (7)0.3414 (5)0.4079 (4)0.041 (2)
C311.1315 (7)0.4202 (5)0.4270 (4)0.046 (2)
H311.18670.45150.45750.055*
C321.0393 (8)0.4507 (5)0.3997 (4)0.046 (2)
C330.9581 (8)0.4048 (5)0.3554 (4)0.044 (2)
H330.89590.42680.33740.053*
C340.8736 (6)0.2733 (4)0.2891 (4)0.041 (2)
H34A0.80430.25840.30880.049*
H34B0.85310.30510.25550.049*
C350.9587 (8)0.2094 (5)0.2050 (4)0.050 (2)
H350.90310.23370.17860.060*
C360.9599 (9)0.1281 (5)0.1695 (5)0.073 (3)
H36A0.88440.09380.16770.088*
H36B1.01770.10180.19160.088*
C370.9880 (11)0.1373 (7)0.1029 (5)0.085 (4)
H37A0.99150.08450.08240.102*
H37B0.92590.15840.07950.102*
C381.0978 (11)0.1911 (7)0.1021 (5)0.090 (4)
H381.15850.16530.12320.108*
C391.1043 (9)0.2720 (7)0.1394 (5)0.087 (3)
H39A1.05280.30290.11720.104*
H39B1.18320.30210.14330.104*
C401.0688 (9)0.2624 (6)0.2064 (5)0.083 (3)
H40A1.12900.24120.23130.100*
H40B1.06420.31530.22630.100*
C410.9815 (6)0.1804 (4)0.6651 (3)0.0342 (19)
C421.0596 (7)0.1269 (5)0.6652 (4)0.043 (2)
C431.1287 (7)0.1243 (5)0.6175 (4)0.054 (2)
H431.17810.08640.61600.064*
C441.1247 (7)0.1775 (6)0.5724 (4)0.053 (2)
H441.17220.17590.54110.063*
C451.0516 (9)0.2321 (5)0.5737 (4)0.059 (3)
H451.05110.26900.54410.071*
C460.9789 (8)0.2331 (5)0.6182 (4)0.049 (2)
H460.92680.26930.61750.059*
C470.8971 (6)0.1786 (4)0.7138 (4)0.038 (2)
H470.83620.13090.70140.046*
C481.0032 (7)0.3208 (5)0.7885 (4)0.037 (2)
C490.9029 (8)0.3203 (5)0.7471 (4)0.042 (2)
C500.8687 (8)0.3950 (6)0.7391 (4)0.054 (2)
C510.9346 (10)0.4662 (5)0.7697 (5)0.072 (3)
H510.91220.51580.76360.086*
C521.0323 (10)0.4621 (6)0.8085 (5)0.070 (3)
C531.0690 (8)0.3894 (6)0.8191 (4)0.054 (2)
H531.13610.38790.84620.065*
C541.0416 (7)0.2411 (5)0.7979 (4)0.047 (2)
H54A1.11060.23920.77770.056*
H54B1.06430.23970.84220.056*
C550.8793 (7)0.1335 (5)0.8192 (4)0.049 (2)
H550.81870.09280.79400.058*
C560.9439 (8)0.0884 (6)0.8639 (4)0.060 (3)
H56A1.00600.12620.88970.072*
H56B0.97940.04950.84080.072*
C570.8643 (9)0.0435 (6)0.9062 (5)0.076 (3)
H57A0.80870.00030.88140.091*
H57B0.91090.01950.93710.091*
C580.8021 (8)0.0999 (6)0.9374 (4)0.063 (3)
H580.85900.14040.96500.075*
C590.7345 (8)0.1427 (6)0.8917 (5)0.069 (3)
H59A0.69480.17990.91390.083*
H59B0.67610.10350.86470.083*
C600.8170 (8)0.1891 (6)0.8529 (4)0.067 (3)
H60A0.77300.21650.82320.081*
H60B0.87300.22990.87990.081*
C610.4694 (6)0.1857 (5)0.6699 (4)0.036 (2)
C620.5409 (7)0.1278 (5)0.6708 (4)0.038 (2)
C630.6068 (7)0.1153 (5)0.6243 (4)0.051 (2)
H630.65300.07540.62510.062*
C640.6023 (9)0.1646 (6)0.5755 (5)0.068 (3)
H640.64410.15570.54250.082*
C650.5389 (8)0.2247 (6)0.5752 (4)0.059 (3)
H650.54070.25890.54360.071*
C660.4717 (7)0.2349 (5)0.6218 (4)0.045 (2)
H660.42680.27560.62110.054*
C670.3914 (7)0.1941 (5)0.7208 (4)0.040 (2)
H670.32890.14660.71400.049*
C680.5023 (7)0.3429 (5)0.7885 (4)0.045 (2)
C690.3967 (7)0.3390 (5)0.7479 (4)0.039 (2)
C700.3564 (8)0.4105 (6)0.7393 (4)0.055 (3)
C710.4159 (9)0.4848 (6)0.7707 (5)0.070 (3)
H710.38800.53240.76420.084*
C720.5144 (10)0.4863 (5)0.8106 (5)0.072 (3)
C730.5602 (8)0.4159 (6)0.8211 (4)0.058 (3)
H730.62740.41790.84900.070*
C740.5474 (7)0.2652 (5)0.7962 (4)0.043 (2)
H74A0.60640.26130.76890.052*
H74B0.58460.26700.83870.052*
C750.3780 (7)0.1742 (5)0.8313 (4)0.043 (2)
H750.30170.18640.81560.051*
C760.3619 (8)0.0868 (5)0.8389 (4)0.054 (2)
H76A0.43710.07280.85280.064*
H76B0.33230.05640.79870.064*
C770.2793 (8)0.0624 (5)0.8848 (4)0.062 (3)
H77A0.27660.00550.89000.074*
H77B0.20160.06970.86840.074*
C780.3163 (7)0.1119 (5)0.9477 (4)0.047 (2)
H780.39190.10020.96530.057*
C790.3307 (9)0.1990 (5)0.9392 (4)0.070 (3)
H79A0.35800.23050.97910.084*
H79B0.25580.21210.92350.084*
C800.4164 (9)0.2215 (5)0.8942 (4)0.064 (3)
H80A0.42370.27890.88980.077*
H80B0.49240.21110.91090.077*
O90.0335 (12)0.3116 (7)0.9790 (6)0.072 (4)0.50
H90.02630.32560.98860.108*0.50
O100.7990 (12)0.3078 (8)1.0151 (6)0.081 (4)0.50
H100.79850.26630.99240.121*0.50
C810.1269 (17)0.3789 (11)0.9909 (10)0.104 (8)0.50
H81A0.09600.42830.99130.155*0.50
H81B0.17630.37710.95880.155*0.50
H81C0.17150.37681.03060.155*0.50
C820.7119 (18)0.3499 (13)0.9890 (11)0.114 (9)0.50
H82A0.69390.38711.02080.170*0.50
H82B0.64280.31170.97230.170*0.50
H82C0.74040.37920.95620.170*0.50
H1A0.609 (7)0.178 (5)0.366 (3)0.080*
H3B1.117 (6)0.184 (4)0.363 (4)0.080*
H5B0.783 (5)0.245 (5)0.685 (3)0.080*
H7B0.278 (5)0.269 (5)0.689 (3)0.080*
H70.528 (8)0.100 (5)0.751 (2)0.080*
H80.193 (7)0.117 (5)1.008 (4)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1302 (11)0.0416 (6)0.0861 (9)0.0253 (6)0.0123 (8)0.0075 (6)
Br20.0457 (6)0.0728 (7)0.0474 (6)0.0083 (5)0.0034 (5)0.0044 (5)
Br30.1229 (10)0.0366 (6)0.0691 (8)0.0169 (6)0.0102 (7)0.0075 (5)
Br40.0435 (6)0.0741 (7)0.0513 (6)0.0068 (5)0.0033 (5)0.0104 (5)
Br50.0702 (7)0.0785 (8)0.0846 (8)0.0348 (6)0.0184 (6)0.0329 (6)
Br60.1881 (16)0.0526 (8)0.1468 (14)0.0179 (9)0.0318 (12)0.0100 (8)
Br70.0655 (7)0.0694 (7)0.0756 (8)0.0291 (6)0.0034 (6)0.0201 (6)
Br80.1732 (15)0.0526 (8)0.1521 (14)0.0194 (8)0.0530 (12)0.0089 (8)
O10.052 (4)0.052 (4)0.051 (4)0.001 (3)0.006 (3)0.000 (3)
O20.154 (8)0.122 (8)0.085 (6)0.064 (6)0.080 (6)0.035 (5)
O30.058 (4)0.061 (4)0.045 (4)0.000 (3)0.004 (3)0.008 (3)
O40.113 (7)0.093 (6)0.057 (5)0.014 (5)0.050 (4)0.002 (4)
O50.068 (5)0.067 (4)0.056 (5)0.030 (4)0.017 (3)0.016 (4)
O60.090 (5)0.075 (5)0.076 (5)0.019 (4)0.047 (4)0.034 (4)
O70.067 (4)0.068 (4)0.056 (5)0.032 (4)0.020 (4)0.010 (4)
O80.076 (5)0.085 (5)0.075 (5)0.021 (4)0.059 (4)0.027 (4)
N10.033 (4)0.035 (4)0.052 (5)0.004 (3)0.003 (4)0.004 (3)
N20.043 (4)0.035 (4)0.030 (4)0.003 (3)0.005 (3)0.003 (3)
N30.044 (5)0.034 (4)0.044 (5)0.008 (3)0.005 (4)0.002 (3)
N40.045 (4)0.033 (4)0.035 (4)0.015 (3)0.003 (3)0.005 (3)
N50.039 (4)0.051 (5)0.040 (5)0.011 (4)0.002 (3)0.007 (4)
N60.030 (4)0.037 (4)0.035 (4)0.001 (3)0.006 (3)0.011 (3)
N70.052 (5)0.044 (4)0.045 (5)0.014 (4)0.009 (4)0.006 (4)
N80.036 (4)0.049 (4)0.036 (4)0.009 (3)0.012 (3)0.009 (3)
C10.043 (5)0.030 (4)0.031 (5)0.012 (4)0.008 (4)0.001 (4)
C20.047 (6)0.029 (5)0.064 (7)0.017 (4)0.019 (5)0.009 (4)
C30.052 (6)0.019 (4)0.090 (8)0.005 (4)0.021 (6)0.019 (5)
C40.063 (7)0.043 (6)0.067 (8)0.011 (5)0.034 (6)0.028 (5)
C50.069 (7)0.052 (6)0.046 (6)0.006 (5)0.017 (6)0.013 (5)
C60.043 (5)0.046 (5)0.053 (6)0.003 (4)0.011 (5)0.007 (5)
C70.037 (5)0.038 (5)0.038 (5)0.013 (4)0.010 (4)0.003 (4)
C80.047 (5)0.034 (5)0.031 (5)0.016 (4)0.010 (4)0.009 (4)
C90.032 (5)0.029 (5)0.036 (5)0.001 (4)0.006 (4)0.006 (4)
C100.038 (5)0.033 (5)0.045 (6)0.005 (4)0.016 (4)0.002 (4)
C110.063 (7)0.047 (6)0.038 (6)0.012 (5)0.006 (5)0.001 (4)
C120.074 (7)0.028 (5)0.047 (6)0.013 (5)0.009 (5)0.001 (4)
C130.054 (6)0.048 (6)0.048 (6)0.023 (5)0.020 (5)0.015 (5)
C140.045 (5)0.052 (6)0.042 (6)0.006 (4)0.004 (4)0.003 (4)
C150.060 (6)0.050 (6)0.031 (5)0.004 (5)0.012 (5)0.009 (4)
C160.069 (7)0.055 (6)0.037 (6)0.006 (5)0.011 (5)0.005 (4)
C170.094 (8)0.051 (6)0.064 (7)0.000 (6)0.027 (6)0.004 (5)
C180.074 (8)0.074 (8)0.057 (7)0.003 (6)0.011 (6)0.008 (6)
C190.075 (7)0.052 (6)0.055 (7)0.001 (5)0.019 (5)0.005 (5)
C200.093 (8)0.044 (6)0.052 (7)0.011 (5)0.034 (6)0.006 (5)
C210.045 (5)0.023 (4)0.046 (6)0.015 (4)0.000 (4)0.006 (4)
C220.049 (6)0.030 (5)0.050 (6)0.007 (4)0.001 (5)0.005 (4)
C230.044 (6)0.040 (5)0.074 (8)0.001 (4)0.014 (6)0.022 (5)
C240.060 (7)0.050 (6)0.070 (8)0.015 (5)0.029 (6)0.027 (5)
C250.074 (8)0.049 (6)0.048 (6)0.011 (5)0.025 (6)0.017 (5)
C260.054 (6)0.045 (5)0.042 (6)0.015 (5)0.010 (5)0.000 (4)
C270.038 (5)0.023 (4)0.043 (5)0.000 (4)0.000 (4)0.005 (4)
C280.038 (5)0.032 (5)0.039 (5)0.000 (4)0.004 (4)0.004 (4)
C290.024 (4)0.033 (5)0.039 (5)0.002 (4)0.014 (4)0.003 (4)
C300.037 (5)0.049 (6)0.039 (5)0.008 (4)0.011 (4)0.012 (4)
C310.058 (6)0.036 (5)0.036 (5)0.006 (5)0.002 (5)0.004 (4)
C320.072 (7)0.030 (5)0.038 (5)0.011 (5)0.013 (5)0.001 (4)
C330.065 (6)0.040 (5)0.029 (5)0.011 (5)0.016 (5)0.003 (4)
C340.037 (5)0.039 (5)0.051 (6)0.008 (4)0.012 (4)0.018 (4)
C350.072 (7)0.037 (5)0.042 (6)0.009 (5)0.014 (5)0.006 (4)
C360.094 (8)0.057 (7)0.066 (8)0.007 (6)0.020 (6)0.008 (5)
C370.123 (11)0.091 (9)0.052 (7)0.051 (8)0.019 (7)0.004 (6)
C380.099 (10)0.087 (9)0.094 (10)0.015 (7)0.068 (8)0.005 (7)
C390.084 (8)0.100 (9)0.076 (8)0.005 (7)0.029 (7)0.018 (7)
C400.084 (8)0.093 (9)0.064 (8)0.017 (7)0.026 (6)0.008 (6)
C410.036 (5)0.034 (5)0.030 (5)0.002 (4)0.008 (4)0.010 (4)
C420.038 (5)0.042 (5)0.050 (6)0.013 (4)0.013 (5)0.007 (4)
C430.050 (6)0.055 (6)0.058 (7)0.012 (5)0.019 (5)0.003 (5)
C440.050 (6)0.075 (7)0.033 (6)0.007 (5)0.021 (5)0.003 (5)
C450.101 (8)0.048 (6)0.040 (6)0.022 (6)0.030 (6)0.020 (5)
C460.074 (7)0.040 (5)0.032 (5)0.003 (5)0.018 (5)0.003 (4)
C470.033 (5)0.029 (4)0.057 (6)0.010 (4)0.011 (4)0.013 (4)
C480.052 (6)0.033 (5)0.033 (5)0.015 (4)0.014 (4)0.006 (4)
C490.051 (6)0.037 (5)0.040 (6)0.000 (5)0.018 (5)0.005 (4)
C500.063 (7)0.052 (6)0.048 (6)0.007 (5)0.008 (5)0.012 (5)
C510.117 (10)0.030 (6)0.076 (8)0.018 (6)0.033 (7)0.015 (5)
C520.088 (8)0.060 (7)0.046 (7)0.013 (6)0.006 (6)0.005 (5)
C530.061 (6)0.049 (6)0.051 (6)0.002 (5)0.013 (5)0.009 (5)
C540.044 (5)0.061 (6)0.035 (5)0.006 (5)0.010 (4)0.004 (4)
C550.055 (6)0.061 (6)0.037 (5)0.019 (5)0.013 (5)0.020 (5)
C560.062 (6)0.076 (7)0.054 (6)0.025 (5)0.029 (5)0.028 (5)
C570.096 (8)0.067 (7)0.079 (8)0.027 (6)0.035 (7)0.025 (6)
C580.074 (7)0.073 (7)0.053 (7)0.024 (6)0.025 (6)0.031 (5)
C590.056 (6)0.100 (8)0.076 (7)0.041 (6)0.044 (6)0.047 (6)
C600.073 (7)0.084 (7)0.064 (7)0.045 (6)0.025 (6)0.027 (6)
C610.033 (5)0.037 (5)0.041 (5)0.006 (4)0.013 (4)0.007 (4)
C620.043 (5)0.038 (5)0.034 (5)0.004 (4)0.007 (4)0.004 (4)
C630.052 (6)0.055 (6)0.046 (6)0.013 (5)0.010 (5)0.005 (5)
C640.071 (7)0.079 (8)0.048 (7)0.009 (6)0.028 (6)0.021 (6)
C650.085 (8)0.053 (6)0.046 (6)0.018 (6)0.022 (6)0.013 (5)
C660.057 (6)0.048 (5)0.035 (5)0.019 (5)0.010 (5)0.009 (4)
C670.039 (5)0.041 (5)0.042 (6)0.010 (4)0.007 (4)0.002 (4)
C680.032 (5)0.066 (6)0.038 (5)0.005 (5)0.009 (4)0.017 (5)
C690.037 (5)0.049 (6)0.038 (5)0.018 (4)0.016 (4)0.011 (4)
C700.049 (6)0.071 (7)0.056 (7)0.018 (5)0.023 (5)0.030 (5)
C710.077 (8)0.045 (6)0.089 (9)0.018 (6)0.004 (7)0.015 (6)
C720.086 (8)0.038 (6)0.083 (8)0.011 (6)0.006 (7)0.014 (5)
C730.053 (6)0.064 (7)0.048 (6)0.016 (5)0.007 (5)0.020 (5)
C740.033 (5)0.069 (6)0.035 (5)0.016 (5)0.020 (4)0.009 (4)
C750.034 (5)0.066 (6)0.036 (5)0.020 (4)0.019 (4)0.015 (4)
C760.069 (7)0.048 (6)0.040 (6)0.009 (5)0.016 (5)0.008 (4)
C770.069 (7)0.056 (6)0.064 (7)0.002 (5)0.033 (6)0.015 (5)
C780.049 (6)0.056 (6)0.045 (6)0.014 (5)0.023 (5)0.014 (5)
C790.124 (9)0.043 (6)0.056 (7)0.019 (6)0.053 (6)0.012 (5)
C800.110 (8)0.047 (6)0.043 (6)0.014 (5)0.041 (6)0.004 (5)
O90.096 (8)0.065 (7)0.053 (7)0.024 (6)0.009 (6)0.006 (6)
O100.094 (8)0.065 (7)0.075 (8)0.006 (6)0.015 (7)0.006 (6)
C810.127 (11)0.108 (11)0.080 (10)0.022 (9)0.009 (8)0.043 (8)
C820.124 (12)0.111 (12)0.100 (12)0.018 (9)0.005 (9)0.003 (9)
Geometric parameters (Å, º) top
Br1—C121.907 (8)C33—H330.9300
Br2—C101.902 (8)C34—H34A0.9700
Br3—C321.903 (7)C34—H34B0.9700
Br4—C301.920 (8)C35—C401.440 (11)
Br5—C501.902 (9)C35—C361.518 (11)
Br6—C521.911 (9)C35—H350.9800
Br7—C701.872 (9)C36—C371.537 (12)
Br8—C721.892 (9)C36—H36A0.9700
O1—C221.376 (9)C36—H36B0.9700
O1—H10.8200C37—C381.450 (14)
O2—C381.429 (11)C37—H37A0.9700
O2—H20.8200C37—H37B0.9700
O3—C21.353 (9)C38—C391.513 (13)
O3—H30.8200C38—H380.9800
O4—C181.425 (10)C39—C401.575 (12)
O4—H40.8200C39—H39A0.9700
O5—C421.359 (9)C39—H39B0.9700
O5—H50.8200C40—H40A0.9700
O6—C581.458 (10)C40—H40B0.9700
O6—H60.8200C41—C421.387 (10)
O7—C621.381 (9)C41—C461.405 (10)
O7—H70.85 (6)C41—C471.531 (10)
O8—C781.419 (9)C42—C431.392 (11)
O8—H80.84 (9)C43—C441.382 (11)
N1—C91.373 (9)C43—H430.9300
N1—C71.467 (9)C44—C451.356 (11)
N1—H1A0.91 (8)C44—H440.9300
N2—C141.468 (9)C45—C461.365 (11)
N2—C151.475 (9)C45—H450.9300
N2—C71.477 (9)C46—H460.9300
N3—C291.394 (9)C47—H470.9800
N3—C271.462 (9)C48—C531.352 (11)
N3—H3B0.91 (8)C48—C491.391 (11)
N4—C271.446 (9)C48—C541.506 (10)
N4—C351.459 (9)C49—C501.400 (11)
N4—C341.465 (9)C50—C511.384 (12)
N5—C491.367 (10)C51—C521.355 (13)
N5—C471.470 (9)C51—H510.9300
N5—H5B0.90 (6)C52—C531.390 (12)
N6—C471.462 (9)C53—H530.9300
N6—C541.464 (9)C54—H54A0.9700
N6—C551.485 (9)C54—H54B0.9700
N7—C691.376 (10)C55—C601.480 (11)
N7—C671.460 (9)C55—C561.493 (10)
N7—H7B0.90 (6)C55—H550.9800
N8—C741.463 (9)C56—C571.541 (11)
N8—C671.469 (9)C56—H56A0.9700
N8—C751.513 (9)C56—H56B0.9700
C1—C61.386 (10)C57—C581.460 (11)
C1—C21.411 (11)C57—H57A0.9700
C1—C71.529 (10)C57—H57B0.9700
C2—C31.403 (11)C58—C591.498 (11)
C3—C41.378 (12)C58—H580.9800
C3—H3A0.9300C59—C601.521 (11)
C4—C51.367 (12)C59—H59A0.9700
C4—H4A0.9300C59—H59B0.9700
C5—C61.361 (11)C60—H60A0.9700
C5—H5A0.9300C60—H60B0.9700
C6—H6A0.9300C61—C661.385 (10)
C7—H7A0.9800C61—C621.385 (10)
C8—C131.379 (10)C61—C671.529 (10)
C8—C91.411 (10)C62—C631.365 (11)
C8—C141.498 (10)C63—C641.400 (12)
C9—C101.395 (10)C63—H630.9300
C10—C111.375 (10)C64—C651.351 (12)
C11—C121.343 (11)C64—H640.9300
C11—H110.9300C65—C661.372 (11)
C12—C131.387 (11)C65—H650.9300
C13—H130.9300C66—H660.9300
C14—H14A0.9700C67—H670.9800
C14—H14B0.9700C68—C731.394 (11)
C15—C201.455 (11)C68—C691.421 (10)
C15—C161.515 (10)C68—C741.502 (11)
C15—H150.9800C69—C701.381 (11)
C16—C171.538 (11)C70—C711.406 (12)
C16—H16A0.9700C71—C721.353 (12)
C16—H16B0.9700C71—H710.9300
C17—C181.453 (12)C72—C731.403 (12)
C17—H17A0.9700C73—H730.9300
C17—H17B0.9700C74—H74A0.9700
C18—C191.505 (11)C74—H74B0.9700
C18—H180.9800C75—C761.477 (10)
C19—C201.508 (11)C75—C801.503 (11)
C19—H19A0.9700C75—H750.9800
C19—H19B0.9700C76—C771.506 (10)
C20—H20A0.9700C76—H76A0.9700
C20—H20B0.9700C76—H76B0.9700
C21—C221.398 (11)C77—C781.518 (11)
C21—C261.411 (10)C77—H77A0.9700
C21—C271.530 (10)C77—H77B0.9700
C22—C231.364 (11)C78—C791.476 (10)
C23—C241.375 (12)C78—H780.9800
C23—H230.9300C79—C801.510 (11)
C24—C251.351 (12)C79—H79A0.9700
C24—H240.9300C79—H79B0.9700
C25—C261.361 (11)C80—H80A0.9700
C25—H250.9300C80—H80B0.9700
C26—H260.9300O9—C811.425 (10)
C27—H270.9800O9—H90.8200
C28—C331.371 (10)O10—C821.427 (9)
C28—C291.392 (10)O10—H100.8200
C28—C341.526 (10)C81—H81A0.9600
C29—C301.374 (10)C81—H81B0.9600
C30—C311.380 (10)C81—H81C0.9600
C31—C321.367 (11)C82—H82A0.9600
C31—H310.9300C82—H82B0.9600
C32—C331.360 (11)C82—H82C0.9600
C22—O1—H1109.5C38—C39—H39B109.2
C38—O2—H2109.5C40—C39—H39B109.2
C2—O3—H3109.5H39A—C39—H39B107.9
C18—O4—H4109.5C35—C40—C39112.6 (9)
C42—O5—H5109.5C35—C40—H40A109.1
C58—O6—H6109.5C39—C40—H40A109.1
C62—O7—H7110 (7)C35—C40—H40B109.1
C78—O8—H8131 (7)C39—C40—H40B109.1
C9—N1—C7117.4 (6)H40A—C40—H40B107.8
C9—N1—H1A120 (6)C42—C41—C46118.5 (8)
C7—N1—H1A109 (6)C42—C41—C47119.9 (7)
C14—N2—C15115.1 (6)C46—C41—C47121.6 (7)
C14—N2—C7109.9 (6)O5—C42—C41122.8 (8)
C15—N2—C7117.2 (6)O5—C42—C43117.9 (7)
C29—N3—C27117.7 (6)C41—C42—C43119.3 (8)
C29—N3—H3B126 (6)C44—C43—C42120.6 (8)
C27—N3—H3B108 (6)C44—C43—H43119.7
C27—N4—C35117.6 (6)C42—C43—H43119.7
C27—N4—C34110.5 (6)C45—C44—C43120.1 (8)
C35—N4—C34113.2 (6)C45—C44—H44120.0
C49—N5—C47117.2 (7)C43—C44—H44120.0
C49—N5—H5B125 (6)C44—C45—C46120.4 (8)
C47—N5—H5B109 (6)C44—C45—H45119.8
C47—N6—C54109.0 (6)C46—C45—H45119.8
C47—N6—C55115.4 (6)C45—C46—C41121.0 (8)
C54—N6—C55117.2 (6)C45—C46—H46119.5
C69—N7—C67119.5 (7)C41—C46—H46119.5
C69—N7—H7B115 (6)N6—C47—N5110.7 (6)
C67—N7—H7B121 (6)N6—C47—C41110.5 (6)
C74—N8—C67109.2 (6)N5—C47—C41114.2 (6)
C74—N8—C75116.9 (6)N6—C47—H47107.0
C67—N8—C75111.9 (6)N5—C47—H47107.0
C6—C1—C2117.3 (8)C41—C47—H47107.0
C6—C1—C7121.4 (7)C53—C48—C49123.2 (8)
C2—C1—C7121.3 (7)C53—C48—C54118.8 (8)
O3—C2—C3119.6 (8)C49—C48—C54118.0 (7)
O3—C2—C1120.9 (8)N5—C49—C48121.1 (8)
C3—C2—C1119.5 (9)N5—C49—C50121.8 (8)
C4—C3—C2119.3 (9)C48—C49—C50117.0 (8)
C4—C3—H3A120.3C51—C50—C49121.0 (9)
C2—C3—H3A120.3C51—C50—Br5119.0 (8)
C5—C4—C3122.1 (9)C49—C50—Br5120.0 (7)
C5—C4—H4A119.0C52—C51—C50118.7 (9)
C3—C4—H4A119.0C52—C51—H51120.7
C6—C5—C4118.1 (9)C50—C51—H51120.7
C6—C5—H5A121.0C51—C52—C53122.7 (9)
C4—C5—H5A121.0C51—C52—Br6118.0 (8)
C5—C6—C1123.7 (8)C53—C52—Br6119.3 (8)
C5—C6—H6A118.2C48—C53—C52117.4 (9)
C1—C6—H6A118.2C48—C53—H53121.3
N1—C7—N2111.0 (6)C52—C53—H53121.3
N1—C7—C1113.9 (6)N6—C54—C48116.7 (7)
N2—C7—C1110.4 (6)N6—C54—H54A108.1
N1—C7—H7A107.1C48—C54—H54A108.1
N2—C7—H7A107.1N6—C54—H54B108.1
C1—C7—H7A107.1C48—C54—H54B108.1
C13—C8—C9118.5 (8)H54A—C54—H54B107.3
C13—C8—C14121.4 (7)C60—C55—N6117.7 (7)
C9—C8—C14119.7 (7)C60—C55—C56110.4 (7)
N1—C9—C10121.9 (7)N6—C55—C56110.4 (7)
N1—C9—C8119.4 (7)C60—C55—H55105.9
C10—C9—C8118.5 (7)N6—C55—H55105.9
C11—C10—C9121.3 (8)C56—C55—H55105.9
C11—C10—Br2119.9 (6)C55—C56—C57112.5 (7)
C9—C10—Br2118.8 (6)C55—C56—H56A109.1
C12—C11—C10120.0 (8)C57—C56—H56A109.1
C12—C11—H11120.0C55—C56—H56B109.1
C10—C11—H11120.0C57—C56—H56B109.1
C11—C12—C13120.5 (8)H56A—C56—H56B107.8
C11—C12—Br1119.7 (7)C58—C57—C56109.9 (8)
C13—C12—Br1119.7 (7)C58—C57—H57A109.7
C8—C13—C12121.2 (8)C56—C57—H57A109.7
C8—C13—H13119.4C58—C57—H57B109.7
C12—C13—H13119.4C56—C57—H57B109.7
N2—C14—C8115.0 (6)H57A—C57—H57B108.2
N2—C14—H14A108.5O6—C58—C57109.3 (8)
C8—C14—H14A108.5O6—C58—C59109.6 (7)
N2—C14—H14B108.5C57—C58—C59111.9 (8)
C8—C14—H14B108.5O6—C58—H58108.6
H14A—C14—H14B107.5C57—C58—H58108.6
C20—C15—N2119.7 (7)C59—C58—H58108.6
C20—C15—C16112.3 (7)C58—C59—C60109.7 (7)
N2—C15—C16111.3 (7)C58—C59—H59A109.7
C20—C15—H15103.8C60—C59—H59A109.7
N2—C15—H15103.8C58—C59—H59B109.7
C16—C15—H15103.8C60—C59—H59B109.7
C15—C16—C17110.1 (7)H59A—C59—H59B108.2
C15—C16—H16A109.6C55—C60—C59110.6 (8)
C17—C16—H16A109.6C55—C60—H60A109.5
C15—C16—H16B109.6C59—C60—H60A109.5
C17—C16—H16B109.6C55—C60—H60B109.5
H16A—C16—H16B108.1C59—C60—H60B109.5
C18—C17—C16114.1 (8)H60A—C60—H60B108.1
C18—C17—H17A108.7C66—C61—C62117.7 (7)
C16—C17—H17A108.7C66—C61—C67121.9 (7)
C18—C17—H17B108.7C62—C61—C67120.4 (7)
C16—C17—H17B108.7C63—C62—O7115.8 (8)
H17A—C17—H17B107.6C63—C62—C61122.1 (8)
O4—C18—C17110.9 (8)O7—C62—C61122.0 (7)
O4—C18—C19112.4 (8)C62—C63—C64117.8 (9)
C17—C18—C19112.2 (8)C62—C63—H63121.1
O4—C18—H18107.0C64—C63—H63121.1
C17—C18—H18107.0C65—C64—C63121.5 (9)
C19—C18—H18107.0C65—C64—H64119.3
C18—C19—C20112.1 (8)C63—C64—H64119.3
C18—C19—H19A109.2C64—C65—C66119.4 (9)
C20—C19—H19A109.2C64—C65—H65120.3
C18—C19—H19B109.2C66—C65—H65120.3
C20—C19—H19B109.2C65—C66—C61121.3 (8)
H19A—C19—H19B107.9C65—C66—H66119.4
C15—C20—C19113.3 (8)C61—C66—H66119.4
C15—C20—H20A108.9N7—C67—N8110.6 (6)
C19—C20—H20A108.9N7—C67—C61113.9 (7)
C15—C20—H20B108.9N8—C67—C61110.1 (6)
C19—C20—H20B108.9N7—C67—H67107.3
H20A—C20—H20B107.7N8—C67—H67107.3
C22—C21—C26115.8 (8)C61—C67—H67107.3
C22—C21—C27120.8 (8)C73—C68—C69120.9 (8)
C26—C21—C27123.3 (8)C73—C68—C74121.4 (8)
C23—C22—O1118.7 (8)C69—C68—C74117.7 (8)
C23—C22—C21121.3 (9)N7—C69—C70121.7 (8)
O1—C22—C21120.0 (8)N7—C69—C68120.4 (7)
C22—C23—C24120.6 (9)C70—C69—C68118.0 (8)
C22—C23—H23119.7C69—C70—C71121.4 (9)
C24—C23—H23119.7C69—C70—Br7121.0 (8)
C25—C24—C23120.1 (9)C71—C70—Br7117.6 (7)
C25—C24—H24119.9C72—C71—C70119.4 (9)
C23—C24—H24119.9C72—C71—H71120.3
C24—C25—C26120.0 (9)C70—C71—H71120.3
C24—C25—H25120.0C71—C72—C73122.0 (9)
C26—C25—H25120.0C71—C72—Br8121.5 (8)
C25—C26—C21122.2 (9)C73—C72—Br8116.6 (8)
C25—C26—H26118.9C68—C73—C72118.3 (8)
C21—C26—H26118.9C68—C73—H73120.9
N4—C27—N3111.8 (6)C72—C73—H73120.9
N4—C27—C21110.5 (6)N8—C74—C68114.0 (6)
N3—C27—C21113.3 (6)N8—C74—H74A108.7
N4—C27—H27107.0C68—C74—H74A108.7
N3—C27—H27107.0N8—C74—H74B108.7
C21—C27—H27107.0C68—C74—H74B108.7
C33—C28—C29120.0 (7)H74A—C74—H74B107.6
C33—C28—C34121.2 (7)C76—C75—C80109.0 (7)
C29—C28—C34118.8 (7)C76—C75—N8109.5 (6)
C30—C29—C28117.7 (7)C80—C75—N8115.8 (7)
C30—C29—N3122.4 (7)C76—C75—H75107.4
C28—C29—N3119.9 (7)C80—C75—H75107.4
C29—C30—C31122.6 (7)N8—C75—H75107.4
C29—C30—Br4119.1 (6)C75—C76—C77113.1 (7)
C31—C30—Br4118.2 (6)C75—C76—H76A109.0
C32—C31—C30117.9 (8)C77—C76—H76A109.0
C32—C31—H31121.0C75—C76—H76B109.0
C30—C31—H31121.0C77—C76—H76B109.0
C33—C32—C31121.1 (8)H76A—C76—H76B107.8
C33—C32—Br3119.8 (7)C76—C77—C78111.8 (7)
C31—C32—Br3119.1 (6)C76—C77—H77A109.3
C32—C33—C28120.8 (8)C78—C77—H77A109.3
C32—C33—H33119.6C76—C77—H77B109.3
C28—C33—H33119.6C78—C77—H77B109.3
N4—C34—C28115.3 (6)H77A—C77—H77B107.9
N4—C34—H34A108.5O8—C78—C79112.2 (7)
C28—C34—H34A108.5O8—C78—C77110.5 (7)
N4—C34—H34B108.5C79—C78—C77109.3 (7)
C28—C34—H34B108.5O8—C78—H78108.2
H34A—C34—H34B107.5C79—C78—H78108.2
C40—C35—N4120.3 (8)C77—C78—H78108.2
C40—C35—C36110.4 (8)C78—C79—C80111.6 (7)
N4—C35—C36111.1 (7)C78—C79—H79A109.3
C40—C35—H35104.5C80—C79—H79A109.3
N4—C35—H35104.5C78—C79—H79B109.3
C36—C35—H35104.5C80—C79—H79B109.3
C35—C36—C37111.7 (8)H79A—C79—H79B108.0
C35—C36—H36A109.3C75—C80—C79111.4 (8)
C37—C36—H36A109.3C75—C80—H80A109.3
C35—C36—H36B109.3C79—C80—H80A109.3
C37—C36—H36B109.3C75—C80—H80B109.3
H36A—C36—H36B107.9C79—C80—H80B109.3
C38—C37—C36112.1 (9)H80A—C80—H80B108.0
C38—C37—H37A109.2C81—O9—H9109.5
C36—C37—H37A109.2C82—O10—H10109.5
C38—C37—H37B109.2O9—C81—H81A109.5
C36—C37—H37B109.2O9—C81—H81B109.5
H37A—C37—H37B107.9H81A—C81—H81B109.5
O2—C38—C37116.8 (11)O9—C81—H81C109.5
O2—C38—C39108.2 (10)H81A—C81—H81C109.5
C37—C38—C39112.4 (9)H81B—C81—H81C109.5
O2—C38—H38106.3O10—C82—H82A109.5
C37—C38—H38106.3O10—C82—H82B109.5
C39—C38—H38106.3H82A—C82—H82B109.5
C38—C39—C40112.2 (9)O10—C82—H82C109.5
C38—C39—H39A109.2H82A—C82—H82C109.5
C40—C39—H39A109.2H82B—C82—H82C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N40.821.932.643 (8)145
N1—H1A···Br20.91 (8)2.69 (7)3.081 (7)107 (6)
O2—H2···O9i0.821.852.660 (15)167
O3—H3···N20.821.932.661 (9)148
N3—H3B···Br40.91 (8)2.77 (8)3.097 (7)103 (5)
O4—H4···O6ii0.822.132.721 (10)129
O5—H5···N60.821.952.650 (9)143
N5—H5B···Br50.90 (6)2.77 (8)3.110 (7)104 (6)
O6—H6···O8iii0.821.952.735 (9)160
O7—H7···N80.85 (6)1.99 (8)2.717 (9)142 (6)
N7—H7B···Br70.90 (6)2.61 (8)3.100 (7)115 (6)
O8—H8···O2iv0.84 (9)1.90 (8)2.713 (11)162 (8)
O9—H9···O10v0.822.182.94 (2)156
Symmetry codes: (i) x+1, y, z1; (ii) x, y, z1; (iii) x+1, y, z+2; (iv) x1, y, z+1; (v) x1, y, z.

Experimental details

Crystal data
Chemical formulaC20H22Br2N2O2·0.25CH4O
Mr490.23
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)11.733 (2), 16.831 (3), 21.721 (4)
α, β, γ (°)94.69 (3), 96.88 (3), 99.44 (3)
V3)4178.4 (14)
Z8
Radiation typeMo Kα
µ (mm1)3.90
Crystal size (mm)0.23 × 0.23 × 0.20
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.468, 0.509
No. of measured, independent and
observed [I > 2σ(I)] reflections
46008, 17573, 6508
Rint0.108
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.087, 0.199, 0.95
No. of reflections17573
No. of parameters1001
No. of restraints38
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.06, 0.78

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
O1—H1···N40.821.932.643 (8)145
N1—H1A···Br20.91 (8)2.69 (7)3.081 (7)107 (6)
O2—H2···O9i0.821.852.660 (15)167
O3—H3···N20.821.932.661 (9)148
N3—H3B···Br40.91 (8)2.77 (8)3.097 (7)103 (5)
O4—H4···O6ii0.822.132.721 (10)129
O5—H5···N60.821.952.650 (9)143
N5—H5B···Br50.90 (6)2.77 (8)3.110 (7)104 (6)
O6—H6···O8iii0.821.952.735 (9)160
O7—H7···N80.85 (6)1.99 (8)2.717 (9)142 (6)
N7—H7B···Br70.90 (6)2.61 (8)3.100 (7)115 (6)
O8—H8···O2iv0.84 (9)1.90 (8)2.713 (11)162 (8)
O9—H9···O10v0.822.182.94 (2)156
Symmetry codes: (i) x+1, y, z1; (ii) x, y, z1; (iii) x+1, y, z+2; (iv) x1, y, z+1; (v) x1, y, z.
 

Acknowledgements

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

References

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Volume 67| Part 4| April 2011| Pages o808-o809
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