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ISSN: 2056-9890

6-Bromo-2-(diprop-2-ynyl­amino)-1H-benzo[de]iso­quinoline-1,3(2H)-dione

aLaboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China, and bSchool of Chemistry and Chemical Engineering, Bijie University, Bijie, Guizhou 551700, People's Republic of China
*Correspondence e-mail: zhouch@swu.edu.cn

(Received 23 April 2012; accepted 17 May 2012; online 23 May 2012)

The asymmetric unit of the title compound, C18H11BrN2O2, contains two independent mol­ecules in which the prop-2-ynyl­amino groups have different mutual orientations. In one mol­ecule, the Br atom is disordered over two positions, with refined occupancies of 0.742 (2) and 0.258 (2).

Related literature

For the applications and biological activity of naphthalimide compounds, see: Muth et al. (2007[Muth, M., Hoerr, V., Glaser, M., Ponte-Sucre, A., Moll, H., Stich, A. & Holzgrabe, U. (2007). Bioorg. Med. Chem. Lett. 17, 1590-1593.]); Zhang & Zhou (2011[Zhang, Y.-Y. & Zhou, C.-H. (2011). Bioorg. Med. Chem. Lett. 21, 4349-4352.]); Zhang et al. (2011[Zhang, Y.-Y., Mi, J.-L., Zhou, C.-H. & Zhou, X.-D. (2011). Eur. J. Med. Chem. 46, 4391-4402.]). For the synthesis, see: Wang et al. (2010[Wang, X.-L., Wan, K. & Zhou, C.-H. (2010). Eur. J. Med. Chem. 45, 5631-4639.]).

[Scheme 1]

Experimental

Crystal data
  • C18H11BrN2O2

  • Mr = 367.20

  • Triclinic, [P \overline 1]

  • a = 10.460 (3) Å

  • b = 11.816 (3) Å

  • c = 13.561 (3) Å

  • α = 75.128 (4)°

  • β = 75.725 (4)°

  • γ = 72.298 (4)°

  • V = 1517.2 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.72 mm−1

  • T = 296 K

  • 0.26 × 0.24 × 0.18 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.538, Tmax = 0.640

  • 8441 measured reflections

  • 5901 independent reflections

  • 3709 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.067

  • wR(F2) = 0.189

  • S = 1.04

  • 5901 reflections

  • 425 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 2.20 e Å−3

  • Δρmin = −0.74 e Å−3

Data collection: APEX2 (Bruker, 2001[Bruker (2001). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). APEX2 and SAINT. 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

Naphthalimide compounds are an important type of cyclic imides with strong hydrophobicity and a desirable large π-conjugated backbone. This special aromatic heterocycle can easily interact with various active targets in biological systems via non-covalent forces such as π···π stacking (Muth et al., 2007), and exhibit diverse biological activities including anticancer, antibacterial, antitrypanosomal, analgesic, photobiological and antinociceptive potency (Zhang & Zhou, 2011). Our interest is to develop novel naphthalimide-derived compounds as potential antimicrobial agents (Zhang et al., 2011). Herein, the crystal structure of the title compound (I) is reported.

The asymmetric unit of (I) is shown in Fig. 1. In the two independent molecules, the prop-2-ynylamino groups have different mutual orientations (see Fig. 1). In one moeclue the Br atom is disordered over two positions with refined occupancies 0.742 (2) and 0.258 (2).

Related literature top

For the applications and biological activity of naphthalimide compounds, see: Muth et al. (2007); Zhang & Zhou (2011); Zhang et al. (2011). For the synthesis, see: Wang et al. (2010).

Experimental top

Compound (I) was prepared according to the procedure of Wang et al. (2010). A mixture of 2-amino-6-bromo-1H-benzo[de]isoquinoline-1,3(2H)-dione (1.00 g, 3.44 mmol), anhydrous potassium carbonate (1.43 g, 10.31 mmol) and propargyl bromide (1.02 g, 8.59 mmol) in N, N-dimethylacetamide (20 ml) was stirred at 353K. After the reaction was complete (monitored by TLC, petroleum ether/ethyl acetate, 3/1, V/V), the solvent was removed. The residue was dissolved in dichloromethane (30 ml) and washed with water (3 x 30 ml). The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure and then purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (10/1–4/1, V/V) to give (I) as yellow solid. Crystals suitable for X-ray analysis were grown from a mixed solution of (I) in ethyl acetate and petroleum ether by slow evaporation at room temperature.

Refinement top

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93-0.97 Å and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), showing displacement ellipsoids are drawn at the 30% probability level. The minor component of disorder is shown with a dashed bond.
6-Bromo-2-(diprop-2-ynylamino)-1H-benzo[de]isoquinoline- 1,3(2H)-dione top
Crystal data top
C18H11BrN2O2Z = 4
Mr = 367.20F(000) = 736
Triclinic, P1Dx = 1.608 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.460 (3) ÅCell parameters from 1880 reflections
b = 11.816 (3) Åθ = 2.4–23.5°
c = 13.561 (3) ŵ = 2.72 mm1
α = 75.128 (4)°T = 296 K
β = 75.725 (4)°Block, yellow
γ = 72.298 (4)°0.26 × 0.24 × 0.18 mm
V = 1517.2 (7) Å3
Data collection top
Bruker APEXII CCD
diffractometer
5901 independent reflections
Radiation source: fine-focus sealed tube3709 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ϕ and ω scansθmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 812
Tmin = 0.538, Tmax = 0.640k = 1214
8441 measured reflectionsl = 1416
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0813P)2 + 2.8703P]
where P = (Fo2 + 2Fc2)/3
5901 reflections(Δ/σ)max < 0.001
425 parametersΔρmax = 2.20 e Å3
1 restraintΔρmin = 0.74 e Å3
Crystal data top
C18H11BrN2O2γ = 72.298 (4)°
Mr = 367.20V = 1517.2 (7) Å3
Triclinic, P1Z = 4
a = 10.460 (3) ÅMo Kα radiation
b = 11.816 (3) ŵ = 2.72 mm1
c = 13.561 (3) ÅT = 296 K
α = 75.128 (4)°0.26 × 0.24 × 0.18 mm
β = 75.725 (4)°
Data collection top
Bruker APEXII CCD
diffractometer
5901 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3709 reflections with I > 2σ(I)
Tmin = 0.538, Tmax = 0.640Rint = 0.023
8441 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0671 restraint
wR(F2) = 0.189H-atom parameters constrained
S = 1.04Δρmax = 2.20 e Å3
5901 reflectionsΔρmin = 0.74 e Å3
425 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
xyzUiso*/UeqOcc. (<1)
Br20.55459 (14)0.50977 (11)0.76724 (11)0.0989 (5)0.742 (2)
C190.6750 (6)0.5968 (6)0.7825 (5)0.0631 (18)
C270.4943 (7)0.6809 (6)0.9230 (5)0.0630 (18)
H270.43520.63870.91770.076*0.742 (2)
Br2'0.3819 (3)0.5988 (3)0.9048 (3)0.0711 (11)0.258 (2)
H19'0.61950.55350.77320.076*0.258 (2)
O31.0432 (4)0.7900 (4)0.7554 (3)0.0576 (11)
O40.7320 (4)0.9391 (4)1.0192 (3)0.0579 (11)
N30.8868 (4)0.8680 (4)0.8839 (3)0.0391 (10)
N40.9653 (5)0.9410 (4)0.8921 (3)0.0429 (11)
C200.7978 (8)0.5865 (6)0.7231 (5)0.0658 (18)
H20A0.82660.53590.67510.079*
C210.8830 (7)0.6511 (6)0.7325 (5)0.0554 (16)
H21A0.96840.64510.68990.067*
C220.8417 (6)0.7239 (5)0.8044 (4)0.0440 (13)
C230.7107 (5)0.7359 (5)0.8683 (4)0.0398 (12)
C240.6694 (5)0.8110 (5)0.9422 (4)0.0384 (12)
C250.5441 (6)0.8219 (6)1.0036 (4)0.0512 (15)
H25A0.51600.87251.05160.061*
C260.4565 (6)0.7562 (6)0.9943 (5)0.0622 (18)
H26A0.37110.76371.03720.075*
C280.6227 (6)0.6695 (5)0.8594 (5)0.0506 (15)
C290.9338 (6)0.7938 (5)0.8102 (4)0.0415 (13)
C300.7610 (5)0.8777 (5)0.9544 (4)0.0416 (13)
C311.0955 (6)0.8715 (6)0.9279 (5)0.0524 (15)
H31A1.15670.83040.87410.063*
H31B1.13890.92690.94060.063*
C321.0719 (6)0.7828 (6)1.0224 (5)0.0516 (15)
C331.0549 (7)0.7110 (6)1.0983 (5)0.0650 (18)
H331.04140.65371.15870.078*
C340.9868 (6)1.0320 (5)0.7990 (5)0.0529 (15)
H34A1.03191.08550.81260.063*
H34B1.04680.99220.74400.063*
C350.8608 (7)1.1035 (6)0.7643 (5)0.0513 (15)
C360.7616 (8)1.1615 (7)0.7340 (6)0.073 (2)
H360.68211.20790.70980.088*
Br10.59705 (8)0.00106 (6)0.23760 (5)0.0651 (3)
O10.5025 (4)0.3271 (4)0.6119 (4)0.0619 (12)
O20.0699 (4)0.2945 (4)0.6614 (3)0.0534 (10)
N10.2845 (4)0.3213 (4)0.6295 (3)0.0384 (10)
N20.2348 (5)0.4032 (4)0.6985 (3)0.0411 (10)
C10.5383 (7)0.0905 (5)0.3449 (4)0.0507 (15)
C20.6289 (6)0.1396 (6)0.3650 (4)0.0513 (15)
H2A0.71690.12890.32600.062*
C30.5900 (6)0.2068 (5)0.4446 (5)0.0526 (15)
H3A0.65250.23890.45930.063*
C40.4603 (6)0.2243 (5)0.4999 (4)0.0431 (13)
C50.3643 (6)0.1758 (4)0.4791 (4)0.0412 (13)
C60.2311 (6)0.1948 (5)0.5347 (4)0.0417 (13)
C70.1384 (6)0.1445 (5)0.5174 (4)0.0500 (14)
H7A0.05010.15770.55570.060*
C80.1779 (7)0.0727 (6)0.4415 (5)0.0566 (16)
H8A0.11620.03700.43040.068*
C90.3051 (7)0.0557 (5)0.3849 (4)0.0536 (15)
H9A0.32860.00970.33380.064*
C100.4030 (6)0.1046 (5)0.4001 (4)0.0470 (14)
C110.1848 (6)0.2737 (5)0.6133 (4)0.0405 (13)
C120.4232 (6)0.2937 (5)0.5833 (4)0.0460 (13)
C130.2805 (6)0.3486 (5)0.7979 (4)0.0514 (15)
H13A0.26030.27030.82440.062*
H13B0.37840.33630.78820.062*
C140.2116 (7)0.4275 (6)0.8720 (5)0.0590 (16)
C150.1620 (9)0.4915 (8)0.9295 (6)0.091 (3)
H150.12180.54350.97620.109*
C160.2598 (6)0.5219 (5)0.6495 (5)0.0499 (14)
H16A0.21960.57680.69770.060*
H16B0.35730.51440.63220.060*
C170.2019 (6)0.5705 (5)0.5570 (5)0.0508 (15)
C180.1566 (8)0.6073 (6)0.4818 (6)0.073 (2)
H180.12030.63700.42130.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br20.1274 (11)0.0833 (8)0.1227 (10)0.0587 (8)0.0590 (8)0.0111 (7)
C190.090 (5)0.042 (4)0.072 (4)0.024 (3)0.040 (4)0.004 (3)
C270.062 (4)0.057 (4)0.073 (4)0.021 (3)0.025 (4)0.000 (4)
Br2'0.0594 (18)0.0600 (18)0.103 (2)0.0243 (13)0.0217 (15)0.0145 (15)
C19'0.090 (5)0.042 (4)0.072 (4)0.024 (3)0.040 (4)0.004 (3)
C27'0.062 (4)0.057 (4)0.073 (4)0.021 (3)0.025 (4)0.000 (4)
O30.045 (2)0.071 (3)0.062 (3)0.021 (2)0.011 (2)0.034 (2)
O40.056 (3)0.072 (3)0.053 (2)0.019 (2)0.008 (2)0.038 (2)
N30.040 (3)0.043 (3)0.037 (2)0.012 (2)0.0010 (19)0.0156 (19)
N40.046 (3)0.046 (3)0.041 (2)0.019 (2)0.008 (2)0.010 (2)
C200.075 (5)0.059 (4)0.072 (4)0.016 (4)0.016 (4)0.026 (4)
C210.060 (4)0.056 (4)0.051 (3)0.009 (3)0.010 (3)0.018 (3)
C220.054 (4)0.035 (3)0.042 (3)0.010 (3)0.007 (3)0.010 (2)
C230.041 (3)0.036 (3)0.042 (3)0.012 (2)0.015 (2)0.002 (2)
C240.040 (3)0.037 (3)0.035 (3)0.007 (2)0.007 (2)0.003 (2)
C250.044 (4)0.055 (4)0.048 (3)0.011 (3)0.009 (3)0.002 (3)
C260.033 (3)0.071 (5)0.071 (4)0.019 (3)0.009 (3)0.011 (4)
C280.058 (4)0.042 (3)0.055 (3)0.016 (3)0.024 (3)0.003 (3)
C290.040 (3)0.043 (3)0.039 (3)0.008 (2)0.005 (3)0.009 (2)
C300.045 (3)0.044 (3)0.035 (3)0.007 (2)0.008 (2)0.010 (2)
C310.055 (4)0.059 (4)0.050 (3)0.022 (3)0.011 (3)0.014 (3)
C320.055 (4)0.057 (4)0.048 (3)0.013 (3)0.012 (3)0.019 (3)
C330.080 (5)0.064 (4)0.051 (4)0.017 (4)0.011 (3)0.016 (3)
C340.058 (4)0.048 (4)0.054 (3)0.018 (3)0.002 (3)0.014 (3)
C350.056 (4)0.049 (4)0.050 (3)0.017 (3)0.012 (3)0.006 (3)
C360.072 (5)0.067 (5)0.081 (5)0.014 (4)0.024 (4)0.011 (4)
Br10.0852 (5)0.0556 (4)0.0410 (3)0.0003 (3)0.0023 (3)0.0167 (3)
O10.047 (3)0.075 (3)0.073 (3)0.019 (2)0.005 (2)0.031 (2)
O20.044 (2)0.075 (3)0.046 (2)0.018 (2)0.0006 (19)0.024 (2)
N10.035 (2)0.038 (2)0.038 (2)0.0026 (19)0.0018 (19)0.0125 (19)
N20.050 (3)0.036 (2)0.038 (2)0.007 (2)0.011 (2)0.0098 (19)
C10.063 (4)0.041 (3)0.034 (3)0.001 (3)0.004 (3)0.005 (2)
C20.041 (3)0.060 (4)0.042 (3)0.007 (3)0.006 (3)0.011 (3)
C30.053 (4)0.045 (3)0.054 (3)0.011 (3)0.003 (3)0.008 (3)
C40.043 (3)0.037 (3)0.039 (3)0.001 (2)0.004 (2)0.004 (2)
C50.056 (4)0.030 (3)0.030 (2)0.004 (2)0.011 (2)0.001 (2)
C60.050 (3)0.039 (3)0.032 (3)0.008 (2)0.008 (2)0.005 (2)
C70.055 (4)0.051 (4)0.046 (3)0.012 (3)0.011 (3)0.015 (3)
C80.066 (4)0.057 (4)0.056 (4)0.020 (3)0.018 (3)0.015 (3)
C90.071 (5)0.046 (4)0.044 (3)0.012 (3)0.011 (3)0.013 (3)
C100.058 (4)0.037 (3)0.033 (3)0.002 (3)0.007 (3)0.001 (2)
C110.050 (4)0.040 (3)0.029 (2)0.009 (3)0.009 (3)0.003 (2)
C120.046 (4)0.041 (3)0.048 (3)0.008 (3)0.012 (3)0.006 (3)
C130.061 (4)0.052 (4)0.040 (3)0.010 (3)0.015 (3)0.006 (3)
C140.069 (4)0.061 (4)0.048 (3)0.010 (3)0.012 (3)0.020 (3)
C150.131 (7)0.081 (6)0.060 (4)0.008 (5)0.021 (5)0.032 (4)
C160.050 (3)0.040 (3)0.059 (3)0.003 (3)0.018 (3)0.010 (3)
C170.061 (4)0.038 (3)0.047 (3)0.002 (3)0.010 (3)0.009 (3)
C180.089 (5)0.054 (4)0.066 (4)0.002 (4)0.020 (4)0.012 (3)
Geometric parameters (Å, º) top
Br2—C191.927 (6)Br1—C11.888 (6)
C19—C201.326 (9)O1—C121.197 (7)
C19—C281.421 (9)O2—C111.202 (6)
C27—C261.386 (9)N1—C121.405 (7)
C27—C281.394 (9)N1—C111.409 (7)
C27—H270.9300N1—N21.415 (6)
O3—C291.196 (6)N2—C161.462 (7)
O4—C301.205 (6)N2—C131.465 (7)
N3—C291.397 (7)C1—C21.361 (9)
N3—N41.399 (6)C1—C101.411 (8)
N3—C301.416 (7)C2—C31.410 (8)
N4—C341.452 (7)C2—H2A0.9300
N4—C311.486 (7)C3—C41.361 (8)
C20—C211.383 (9)C3—H3A0.9300
C20—H20A0.9300C4—C51.409 (8)
C21—C221.369 (8)C4—C121.473 (8)
C21—H21A0.9300C5—C61.392 (8)
C22—C231.417 (8)C5—C101.437 (8)
C22—C291.474 (8)C6—C71.372 (8)
C23—C241.411 (7)C6—C111.491 (7)
C23—C281.421 (8)C7—C81.405 (8)
C24—C251.357 (8)C7—H7A0.9300
C24—C301.473 (8)C8—C91.346 (9)
C25—C261.414 (9)C8—H8A0.9300
C25—H25A0.9300C9—C101.396 (9)
C26—H26A0.9300C9—H9A0.9300
C31—C321.454 (9)C13—C141.453 (8)
C31—H31A0.9700C13—H13A0.9700
C31—H31B0.9700C13—H13B0.9700
C32—C331.168 (9)C14—C151.147 (9)
C33—H330.9300C15—H150.9300
C34—C351.449 (9)C16—C171.436 (8)
C34—H34A0.9700C16—H16A0.9700
C34—H34B0.9700C16—H16B0.9700
C35—C361.161 (9)C17—C181.157 (9)
C36—H360.9300C18—H180.9300
C20—C19—C28124.4 (6)C12—N1—C11125.4 (4)
C20—C19—Br2120.0 (5)C12—N1—N2120.1 (4)
C28—C19—Br2115.6 (5)C11—N1—N2114.5 (4)
C26—C27—C28118.8 (6)N1—N2—C16111.9 (4)
C26—C27—H27120.6N1—N2—C13111.2 (4)
C28—C27—H27120.6C16—N2—C13115.4 (4)
C29—N3—N4120.3 (4)C2—C1—C10122.8 (5)
C29—N3—C30125.2 (5)C2—C1—Br1118.2 (4)
N4—N3—C30114.5 (4)C10—C1—Br1119.0 (5)
N3—N4—C34113.2 (4)C1—C2—C3120.3 (5)
N3—N4—C31113.7 (4)C1—C2—H2A119.9
C34—N4—C31111.7 (4)C3—C2—H2A119.9
C19—C20—C21119.9 (6)C4—C3—C2119.5 (6)
C19—C20—H20A120.0C4—C3—H3A120.2
C21—C20—H20A120.0C2—C3—H3A120.2
C22—C21—C20120.1 (6)C3—C4—C5121.1 (5)
C22—C21—H21A120.0C3—C4—C12118.2 (6)
C20—C21—H21A120.0C5—C4—C12120.7 (5)
C21—C22—C23120.6 (6)C6—C5—C4121.2 (5)
C21—C22—C29118.5 (5)C6—C5—C10118.6 (5)
C23—C22—C29120.8 (5)C4—C5—C10120.2 (5)
C24—C23—C22120.1 (5)C7—C6—C5121.5 (5)
C24—C23—C28120.2 (5)C7—C6—C11118.2 (5)
C22—C23—C28119.7 (5)C5—C6—C11120.2 (5)
C25—C24—C23119.9 (5)C6—C7—C8119.5 (6)
C25—C24—C30119.2 (5)C6—C7—H7A120.2
C23—C24—C30120.9 (5)C8—C7—H7A120.2
C24—C25—C26119.7 (6)C9—C8—C7120.0 (6)
C24—C25—H25A120.1C9—C8—H8A120.0
C26—C25—H25A120.1C7—C8—H8A120.0
C27—C26—C25121.8 (6)C8—C9—C10122.5 (6)
C27—C26—H26A119.1C8—C9—H9A118.8
C25—C26—H26A119.1C10—C9—H9A118.8
C27—C28—C19125.2 (6)C9—C10—C1126.1 (6)
C27—C28—C23119.5 (6)C9—C10—C5117.8 (5)
C19—C28—C23115.3 (6)C1—C10—C5116.1 (6)
O3—C29—N3120.2 (5)O2—C11—N1121.6 (5)
O3—C29—C22123.2 (5)O2—C11—C6122.4 (5)
N3—C29—C22116.6 (5)N1—C11—C6116.0 (5)
O4—C30—N3120.6 (5)O1—C12—N1119.9 (5)
O4—C30—C24123.1 (5)O1—C12—C4124.3 (5)
N3—C30—C24116.3 (4)N1—C12—C4115.8 (5)
C32—C31—N4111.0 (5)C14—C13—N2109.8 (5)
C32—C31—H31A109.4C14—C13—H13A109.7
N4—C31—H31A109.4N2—C13—H13A109.7
C32—C31—H31B109.4C14—C13—H13B109.7
N4—C31—H31B109.4N2—C13—H13B109.7
H31A—C31—H31B108.0H13A—C13—H13B108.2
C33—C32—C31179.0 (7)C15—C14—C13177.1 (9)
C32—C33—H33180.0C14—C15—H15180.0
C35—C34—N4112.8 (5)C17—C16—N2110.5 (5)
C35—C34—H34A109.0C17—C16—H16A109.5
N4—C34—H34A109.0N2—C16—H16A109.5
C35—C34—H34B109.0C17—C16—H16B109.5
N4—C34—H34B109.0N2—C16—H16B109.5
H34A—C34—H34B107.8H16A—C16—H16B108.1
C36—C35—C34178.3 (7)C18—C17—C16178.6 (7)
C35—C36—H36180.0C17—C18—H18180.0
C29—N3—N4—C3462.9 (6)C12—N1—N2—C1658.3 (6)
C30—N3—N4—C34116.9 (5)C11—N1—N2—C16121.7 (5)
C29—N3—N4—C3166.0 (6)C12—N1—N2—C1372.5 (6)
C30—N3—N4—C31114.2 (5)C11—N1—N2—C13107.6 (5)
C28—C19—C20—C211.4 (10)C10—C1—C2—C30.8 (9)
Br2—C19—C20—C21178.6 (5)Br1—C1—C2—C3179.7 (4)
C19—C20—C21—C221.2 (10)C1—C2—C3—C41.4 (9)
C20—C21—C22—C231.3 (9)C2—C3—C4—C50.3 (8)
C20—C21—C22—C29178.4 (5)C2—C3—C4—C12179.4 (5)
C21—C22—C23—C24179.9 (5)C3—C4—C5—C6179.2 (5)
C29—C22—C23—C243.1 (8)C12—C4—C5—C61.8 (7)
C21—C22—C23—C281.5 (8)C3—C4—C5—C101.3 (8)
C29—C22—C23—C28178.5 (5)C12—C4—C5—C10177.8 (5)
C22—C23—C24—C25179.8 (5)C4—C5—C6—C7177.7 (5)
C28—C23—C24—C251.4 (7)C10—C5—C6—C71.8 (7)
C22—C23—C24—C300.1 (7)C4—C5—C6—C113.8 (7)
C28—C23—C24—C30178.3 (5)C10—C5—C6—C11176.7 (4)
C23—C24—C25—C261.1 (8)C5—C6—C7—C80.5 (8)
C30—C24—C25—C26178.5 (5)C11—C6—C7—C8178.1 (5)
C28—C27—C26—C250.4 (9)C6—C7—C8—C91.3 (9)
C24—C25—C26—C270.6 (9)C7—C8—C9—C101.7 (9)
C26—C27—C28—C19179.5 (6)C8—C9—C10—C1179.6 (6)
C26—C27—C28—C230.6 (9)C8—C9—C10—C50.3 (8)
C20—C19—C28—C27179.6 (6)C2—C1—C10—C9179.1 (6)
Br2—C19—C28—C270.5 (8)Br1—C1—C10—C91.5 (8)
C20—C19—C28—C231.5 (9)C2—C1—C10—C50.8 (8)
Br2—C19—C28—C23178.4 (4)Br1—C1—C10—C5178.7 (4)
C24—C23—C28—C271.1 (8)C6—C5—C10—C91.5 (7)
C22—C23—C28—C27179.5 (5)C4—C5—C10—C9178.1 (5)
C24—C23—C28—C19179.9 (5)C6—C5—C10—C1178.7 (5)
C22—C23—C28—C191.5 (7)C4—C5—C10—C11.8 (7)
N4—N3—C29—O31.8 (8)C12—N1—C11—O2174.4 (5)
C30—N3—C29—O3178.4 (5)N2—N1—C11—O25.6 (7)
N4—N3—C29—C22177.6 (4)C12—N1—C11—C64.6 (7)
C30—N3—C29—C222.2 (7)N2—N1—C11—C6175.3 (4)
C21—C22—C29—O30.2 (8)C7—C6—C11—O20.2 (8)
C23—C22—C29—O3177.3 (5)C5—C6—C11—O2178.4 (5)
C21—C22—C29—N3179.2 (5)C7—C6—C11—N1178.9 (5)
C23—C22—C29—N32.1 (7)C5—C6—C11—N12.5 (7)
C29—N3—C30—O4175.9 (5)C11—N1—C12—O1170.7 (5)
N4—N3—C30—O44.4 (7)N2—N1—C12—O19.4 (8)
C29—N3—C30—C245.1 (7)C11—N1—C12—C49.8 (7)
N4—N3—C30—C24174.6 (4)N2—N1—C12—C4170.1 (4)
C25—C24—C30—O42.6 (8)C3—C4—C12—O16.8 (9)
C23—C24—C30—O4177.0 (5)C5—C4—C12—O1172.3 (5)
C25—C24—C30—N3176.3 (5)C3—C4—C12—N1172.8 (5)
C23—C24—C30—N34.0 (7)C5—C4—C12—N18.2 (7)
N3—N4—C31—C3251.7 (6)N1—N2—C13—C14171.5 (5)
C34—N4—C31—C32178.6 (5)C16—N2—C13—C1459.6 (7)
N4—C31—C32—C33176 (100)N2—C13—C14—C1599 (15)
N3—N4—C34—C3551.8 (6)N1—N2—C16—C1755.8 (6)
C31—N4—C34—C35178.3 (5)C13—N2—C16—C17175.6 (5)
N4—C34—C35—C36157 (25)N2—C16—C17—C1852 (32)

Experimental details

Crystal data
Chemical formulaC18H11BrN2O2
Mr367.20
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)10.460 (3), 11.816 (3), 13.561 (3)
α, β, γ (°)75.128 (4), 75.725 (4), 72.298 (4)
V3)1517.2 (7)
Z4
Radiation typeMo Kα
µ (mm1)2.72
Crystal size (mm)0.26 × 0.24 × 0.18
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.538, 0.640
No. of measured, independent and
observed [I > 2σ(I)] reflections
8441, 5901, 3709
Rint0.023
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.189, 1.04
No. of reflections5901
No. of parameters425
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)2.20, 0.74

Computer programs: APEX2 (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was partially supported by the National Natural Science Foundation of China (No. 21172181), the key program of the Natural Science Foundation of Chongqing (CSTC2012jjB10026), the Specialized Research Fund for the Doctoral Program of Higher Education of China (SRFDP 20110182110007), the Research Funds for the Central Universities (XDJK2012B026) and the Early Career Development Fellowship Program of Bijie University (20102002).

References

First citationBruker (2001). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationMuth, M., Hoerr, V., Glaser, M., Ponte-Sucre, A., Moll, H., Stich, A. & Holzgrabe, U. (2007). Bioorg. Med. Chem. Lett. 17, 1590–1593.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, X.-L., Wan, K. & Zhou, C.-H. (2010). Eur. J. Med. Chem. 45, 5631-4639.  Google Scholar
First citationZhang, Y.-Y., Mi, J.-L., Zhou, C.-H. & Zhou, X.-D. (2011). Eur. J. Med. Chem. 46, 4391–4402.  Web of Science CrossRef CAS PubMed Google Scholar
First citationZhang, Y.-Y. & Zhou, C.-H. (2011). Bioorg. Med. Chem. Lett. 21, 4349–4352.  Web of Science CrossRef CAS PubMed Google Scholar

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