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

Lv, J.-S.; Wang, J.-L.; Zhou, C.-H.

doi:10.1107/S1600536812022507

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1852

doi:10.1107/S1600536812022507

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

Jing-Song Lv,^a,^b Jun-Lei Wang ^b and Cheng-He Zhou ^a ^*

^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 ); Zhang & Zhou (2011 ); Zhang et al. (2011 ). For the synthesis, see: Wang et al. (2010 ).

Experimental

Crystal data

C₁₈H₁₁BrN₂O₂
M_r = 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 ) T_min = 0.538, T_max = 0.640
8441 measured reflections
5901 independent reflections
3709 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 2.20 e Å⁻³
Δρ_min = −0.74 e Å⁻³

Data collection: APEX2 (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812022507/lh5464sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022507/lh5464Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022507/lh5464Isup3.cml

checkCIF report

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.

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

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

C₁₈H₁₁BrN₂O₂	Z = 4
M_r = 367.20	F(000) = 736
Triclinic, P1	D_x = 1.608 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.460 (3) Å	Cell parameters from 1880 reflections
b = 11.816 (3) Å	θ = 2.4–23.5°
c = 13.561 (3) Å	µ = 2.72 mm⁻¹
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 tube	3709 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→12
T_min = 0.538, T_max = 0.640	k = −12→14
8441 measured reflections	l = −14→16

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.189	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0813P)² + 2.8703P] where P = (F_o² + 2F_c²)/3
5901 reflections	(Δ/σ)_max < 0.001
425 parameters	Δρ_max = 2.20 e Å⁻³
1 restraint	Δρ_min = −0.74 e Å⁻³

Crystal data top

C₁₈H₁₁BrN₂O₂	γ = 72.298 (4)°
M_r = 367.20	V = 1517.2 (7) Å³
Triclinic, P1	Z = 4
a = 10.460 (3) Å	Mo Kα radiation
b = 11.816 (3) Å	µ = 2.72 mm⁻¹
c = 13.561 (3) Å	T = 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)
T_min = 0.538, T_max = 0.640	R_int = 0.023
8441 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	1 restraint
wR(F²) = 0.189	H-atom parameters constrained
S = 1.04	Δρ_max = 2.20 e Å⁻³
5901 reflections	Δρ_min = −0.74 e Å⁻³
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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br2	0.55459 (14)	0.50977 (11)	0.76724 (11)	0.0989 (5)	0.742 (2)
C19	0.6750 (6)	0.5968 (6)	0.7825 (5)	0.0631 (18)
C27	0.4943 (7)	0.6809 (6)	0.9230 (5)	0.0630 (18)
H27	0.4352	0.6387	0.9177	0.076*	0.742 (2)
Br2'	0.3819 (3)	0.5988 (3)	0.9048 (3)	0.0711 (11)	0.258 (2)
H19'	0.6195	0.5535	0.7732	0.076*	0.258 (2)
O3	1.0432 (4)	0.7900 (4)	0.7554 (3)	0.0576 (11)
O4	0.7320 (4)	0.9391 (4)	1.0192 (3)	0.0579 (11)
N3	0.8868 (4)	0.8680 (4)	0.8839 (3)	0.0391 (10)
N4	0.9653 (5)	0.9410 (4)	0.8921 (3)	0.0429 (11)
C20	0.7978 (8)	0.5865 (6)	0.7231 (5)	0.0658 (18)
H20A	0.8266	0.5359	0.6751	0.079*
C21	0.8830 (7)	0.6511 (6)	0.7325 (5)	0.0554 (16)
H21A	0.9684	0.6451	0.6899	0.067*
C22	0.8417 (6)	0.7239 (5)	0.8044 (4)	0.0440 (13)
C23	0.7107 (5)	0.7359 (5)	0.8683 (4)	0.0398 (12)
C24	0.6694 (5)	0.8110 (5)	0.9422 (4)	0.0384 (12)
C25	0.5441 (6)	0.8219 (6)	1.0036 (4)	0.0512 (15)
H25A	0.5160	0.8725	1.0516	0.061*
C26	0.4565 (6)	0.7562 (6)	0.9943 (5)	0.0622 (18)
H26A	0.3711	0.7637	1.0372	0.075*
C28	0.6227 (6)	0.6695 (5)	0.8594 (5)	0.0506 (15)
C29	0.9338 (6)	0.7938 (5)	0.8102 (4)	0.0415 (13)
C30	0.7610 (5)	0.8777 (5)	0.9544 (4)	0.0416 (13)
C31	1.0955 (6)	0.8715 (6)	0.9279 (5)	0.0524 (15)
H31A	1.1567	0.8304	0.8741	0.063*
H31B	1.1389	0.9269	0.9406	0.063*
C32	1.0719 (6)	0.7828 (6)	1.0224 (5)	0.0516 (15)
C33	1.0549 (7)	0.7110 (6)	1.0983 (5)	0.0650 (18)
H33	1.0414	0.6537	1.1587	0.078*
C34	0.9868 (6)	1.0320 (5)	0.7990 (5)	0.0529 (15)
H34A	1.0319	1.0855	0.8126	0.063*
H34B	1.0468	0.9922	0.7440	0.063*
C35	0.8608 (7)	1.1035 (6)	0.7643 (5)	0.0513 (15)
C36	0.7616 (8)	1.1615 (7)	0.7340 (6)	0.073 (2)
H36	0.6821	1.2079	0.7098	0.088*
Br1	0.59705 (8)	0.00106 (6)	0.23760 (5)	0.0651 (3)
O1	0.5025 (4)	0.3271 (4)	0.6119 (4)	0.0619 (12)
O2	0.0699 (4)	0.2945 (4)	0.6614 (3)	0.0534 (10)
N1	0.2845 (4)	0.3213 (4)	0.6295 (3)	0.0384 (10)
N2	0.2348 (5)	0.4032 (4)	0.6985 (3)	0.0411 (10)
C1	0.5383 (7)	0.0905 (5)	0.3449 (4)	0.0507 (15)
C2	0.6289 (6)	0.1396 (6)	0.3650 (4)	0.0513 (15)
H2A	0.7169	0.1289	0.3260	0.062*
C3	0.5900 (6)	0.2068 (5)	0.4446 (5)	0.0526 (15)
H3A	0.6525	0.2389	0.4593	0.063*
C4	0.4603 (6)	0.2243 (5)	0.4999 (4)	0.0431 (13)
C5	0.3643 (6)	0.1758 (4)	0.4791 (4)	0.0412 (13)
C6	0.2311 (6)	0.1948 (5)	0.5347 (4)	0.0417 (13)
C7	0.1384 (6)	0.1445 (5)	0.5174 (4)	0.0500 (14)
H7A	0.0501	0.1577	0.5557	0.060*
C8	0.1779 (7)	0.0727 (6)	0.4415 (5)	0.0566 (16)
H8A	0.1162	0.0370	0.4304	0.068*
C9	0.3051 (7)	0.0557 (5)	0.3849 (4)	0.0536 (15)
H9A	0.3286	0.0097	0.3338	0.064*
C10	0.4030 (6)	0.1046 (5)	0.4001 (4)	0.0470 (14)
C11	0.1848 (6)	0.2737 (5)	0.6133 (4)	0.0405 (13)
C12	0.4232 (6)	0.2937 (5)	0.5833 (4)	0.0460 (13)
C13	0.2805 (6)	0.3486 (5)	0.7979 (4)	0.0514 (15)
H13A	0.2603	0.2703	0.8244	0.062*
H13B	0.3784	0.3363	0.7882	0.062*
C14	0.2116 (7)	0.4275 (6)	0.8720 (5)	0.0590 (16)
C15	0.1620 (9)	0.4915 (8)	0.9295 (6)	0.091 (3)
H15	0.1218	0.5435	0.9762	0.109*
C16	0.2598 (6)	0.5219 (5)	0.6495 (5)	0.0499 (14)
H16A	0.2196	0.5768	0.6977	0.060*
H16B	0.3573	0.5144	0.6322	0.060*
C17	0.2019 (6)	0.5705 (5)	0.5570 (5)	0.0508 (15)
C18	0.1566 (8)	0.6073 (6)	0.4818 (6)	0.073 (2)
H18	0.1203	0.6370	0.4213	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br2	0.1274 (11)	0.0833 (8)	0.1227 (10)	−0.0587 (8)	−0.0590 (8)	−0.0111 (7)
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)
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)
O3	0.045 (2)	0.071 (3)	0.062 (3)	−0.021 (2)	0.011 (2)	−0.034 (2)
O4	0.056 (3)	0.072 (3)	0.053 (2)	−0.019 (2)	0.008 (2)	−0.038 (2)
N3	0.040 (3)	0.043 (3)	0.037 (2)	−0.012 (2)	−0.0010 (19)	−0.0156 (19)
N4	0.046 (3)	0.046 (3)	0.041 (2)	−0.019 (2)	−0.008 (2)	−0.010 (2)
C20	0.075 (5)	0.059 (4)	0.072 (4)	−0.016 (4)	−0.016 (4)	−0.026 (4)
C21	0.060 (4)	0.056 (4)	0.051 (3)	−0.009 (3)	−0.010 (3)	−0.018 (3)
C22	0.054 (4)	0.035 (3)	0.042 (3)	−0.010 (3)	−0.007 (3)	−0.010 (2)
C23	0.041 (3)	0.036 (3)	0.042 (3)	−0.012 (2)	−0.015 (2)	0.002 (2)
C24	0.040 (3)	0.037 (3)	0.035 (3)	−0.007 (2)	−0.007 (2)	−0.003 (2)
C25	0.044 (4)	0.055 (4)	0.048 (3)	−0.011 (3)	−0.009 (3)	−0.002 (3)
C26	0.033 (3)	0.071 (5)	0.071 (4)	−0.019 (3)	−0.009 (3)	0.011 (4)
C28	0.058 (4)	0.042 (3)	0.055 (3)	−0.016 (3)	−0.024 (3)	0.003 (3)
C29	0.040 (3)	0.043 (3)	0.039 (3)	−0.008 (2)	−0.005 (3)	−0.009 (2)
C30	0.045 (3)	0.044 (3)	0.035 (3)	−0.007 (2)	−0.008 (2)	−0.010 (2)
C31	0.055 (4)	0.059 (4)	0.050 (3)	−0.022 (3)	−0.011 (3)	−0.014 (3)
C32	0.055 (4)	0.057 (4)	0.048 (3)	−0.013 (3)	−0.012 (3)	−0.019 (3)
C33	0.080 (5)	0.064 (4)	0.051 (4)	−0.017 (4)	−0.011 (3)	−0.016 (3)
C34	0.058 (4)	0.048 (4)	0.054 (3)	−0.018 (3)	−0.002 (3)	−0.014 (3)
C35	0.056 (4)	0.049 (4)	0.050 (3)	−0.017 (3)	−0.012 (3)	−0.006 (3)
C36	0.072 (5)	0.067 (5)	0.081 (5)	−0.014 (4)	−0.024 (4)	−0.011 (4)
Br1	0.0852 (5)	0.0556 (4)	0.0410 (3)	−0.0003 (3)	−0.0023 (3)	−0.0167 (3)
O1	0.047 (3)	0.075 (3)	0.073 (3)	−0.019 (2)	−0.005 (2)	−0.031 (2)
O2	0.044 (2)	0.075 (3)	0.046 (2)	−0.018 (2)	−0.0006 (19)	−0.024 (2)
N1	0.035 (2)	0.038 (2)	0.038 (2)	−0.0026 (19)	−0.0018 (19)	−0.0125 (19)
N2	0.050 (3)	0.036 (2)	0.038 (2)	−0.007 (2)	−0.011 (2)	−0.0098 (19)
C1	0.063 (4)	0.041 (3)	0.034 (3)	−0.001 (3)	−0.004 (3)	−0.005 (2)
C2	0.041 (3)	0.060 (4)	0.042 (3)	−0.007 (3)	0.006 (3)	−0.011 (3)
C3	0.053 (4)	0.045 (3)	0.054 (3)	−0.011 (3)	−0.003 (3)	−0.008 (3)
C4	0.043 (3)	0.037 (3)	0.039 (3)	−0.001 (2)	−0.004 (2)	−0.004 (2)
C5	0.056 (4)	0.030 (3)	0.030 (2)	−0.004 (2)	−0.011 (2)	0.001 (2)
C6	0.050 (3)	0.039 (3)	0.032 (3)	−0.008 (2)	−0.008 (2)	−0.005 (2)
C7	0.055 (4)	0.051 (4)	0.046 (3)	−0.012 (3)	−0.011 (3)	−0.015 (3)
C8	0.066 (4)	0.057 (4)	0.056 (4)	−0.020 (3)	−0.018 (3)	−0.015 (3)
C9	0.071 (5)	0.046 (4)	0.044 (3)	−0.012 (3)	−0.011 (3)	−0.013 (3)
C10	0.058 (4)	0.037 (3)	0.033 (3)	−0.002 (3)	−0.007 (3)	0.001 (2)
C11	0.050 (4)	0.040 (3)	0.029 (2)	−0.009 (3)	−0.009 (3)	−0.003 (2)
C12	0.046 (4)	0.041 (3)	0.048 (3)	−0.008 (3)	−0.012 (3)	−0.006 (3)
C13	0.061 (4)	0.052 (4)	0.040 (3)	−0.010 (3)	−0.015 (3)	−0.006 (3)
C14	0.069 (4)	0.061 (4)	0.048 (3)	−0.010 (3)	−0.012 (3)	−0.020 (3)
C15	0.131 (7)	0.081 (6)	0.060 (4)	−0.008 (5)	−0.021 (5)	−0.032 (4)
C16	0.050 (3)	0.040 (3)	0.059 (3)	−0.003 (3)	−0.018 (3)	−0.010 (3)
C17	0.061 (4)	0.038 (3)	0.047 (3)	−0.002 (3)	−0.010 (3)	−0.009 (3)
C18	0.089 (5)	0.054 (4)	0.066 (4)	0.002 (4)	−0.020 (4)	−0.012 (3)

Geometric parameters (Å, º) top

Br2—C19	1.927 (6)	Br1—C1	1.888 (6)
C19—C20	1.326 (9)	O1—C12	1.197 (7)
C19—C28	1.421 (9)	O2—C11	1.202 (6)
C27—C26	1.386 (9)	N1—C12	1.405 (7)
C27—C28	1.394 (9)	N1—C11	1.409 (7)
C27—H27	0.9300	N1—N2	1.415 (6)
O3—C29	1.196 (6)	N2—C16	1.462 (7)
O4—C30	1.205 (6)	N2—C13	1.465 (7)
N3—C29	1.397 (7)	C1—C2	1.361 (9)
N3—N4	1.399 (6)	C1—C10	1.411 (8)
N3—C30	1.416 (7)	C2—C3	1.410 (8)
N4—C34	1.452 (7)	C2—H2A	0.9300
N4—C31	1.486 (7)	C3—C4	1.361 (8)
C20—C21	1.383 (9)	C3—H3A	0.9300
C20—H20A	0.9300	C4—C5	1.409 (8)
C21—C22	1.369 (8)	C4—C12	1.473 (8)
C21—H21A	0.9300	C5—C6	1.392 (8)
C22—C23	1.417 (8)	C5—C10	1.437 (8)
C22—C29	1.474 (8)	C6—C7	1.372 (8)
C23—C24	1.411 (7)	C6—C11	1.491 (7)
C23—C28	1.421 (8)	C7—C8	1.405 (8)
C24—C25	1.357 (8)	C7—H7A	0.9300
C24—C30	1.473 (8)	C8—C9	1.346 (9)
C25—C26	1.414 (9)	C8—H8A	0.9300
C25—H25A	0.9300	C9—C10	1.396 (9)
C26—H26A	0.9300	C9—H9A	0.9300
C31—C32	1.454 (9)	C13—C14	1.453 (8)
C31—H31A	0.9700	C13—H13A	0.9700
C31—H31B	0.9700	C13—H13B	0.9700
C32—C33	1.168 (9)	C14—C15	1.147 (9)
C33—H33	0.9300	C15—H15	0.9300
C34—C35	1.449 (9)	C16—C17	1.436 (8)
C34—H34A	0.9700	C16—H16A	0.9700
C34—H34B	0.9700	C16—H16B	0.9700
C35—C36	1.161 (9)	C17—C18	1.157 (9)
C36—H36	0.9300	C18—H18	0.9300

C20—C19—C28	124.4 (6)	C12—N1—C11	125.4 (4)
C20—C19—Br2	120.0 (5)	C12—N1—N2	120.1 (4)
C28—C19—Br2	115.6 (5)	C11—N1—N2	114.5 (4)
C26—C27—C28	118.8 (6)	N1—N2—C16	111.9 (4)
C26—C27—H27	120.6	N1—N2—C13	111.2 (4)
C28—C27—H27	120.6	C16—N2—C13	115.4 (4)
C29—N3—N4	120.3 (4)	C2—C1—C10	122.8 (5)
C29—N3—C30	125.2 (5)	C2—C1—Br1	118.2 (4)
N4—N3—C30	114.5 (4)	C10—C1—Br1	119.0 (5)
N3—N4—C34	113.2 (4)	C1—C2—C3	120.3 (5)
N3—N4—C31	113.7 (4)	C1—C2—H2A	119.9
C34—N4—C31	111.7 (4)	C3—C2—H2A	119.9
C19—C20—C21	119.9 (6)	C4—C3—C2	119.5 (6)
C19—C20—H20A	120.0	C4—C3—H3A	120.2
C21—C20—H20A	120.0	C2—C3—H3A	120.2
C22—C21—C20	120.1 (6)	C3—C4—C5	121.1 (5)
C22—C21—H21A	120.0	C3—C4—C12	118.2 (6)
C20—C21—H21A	120.0	C5—C4—C12	120.7 (5)
C21—C22—C23	120.6 (6)	C6—C5—C4	121.2 (5)
C21—C22—C29	118.5 (5)	C6—C5—C10	118.6 (5)
C23—C22—C29	120.8 (5)	C4—C5—C10	120.2 (5)
C24—C23—C22	120.1 (5)	C7—C6—C5	121.5 (5)
C24—C23—C28	120.2 (5)	C7—C6—C11	118.2 (5)
C22—C23—C28	119.7 (5)	C5—C6—C11	120.2 (5)
C25—C24—C23	119.9 (5)	C6—C7—C8	119.5 (6)
C25—C24—C30	119.2 (5)	C6—C7—H7A	120.2
C23—C24—C30	120.9 (5)	C8—C7—H7A	120.2
C24—C25—C26	119.7 (6)	C9—C8—C7	120.0 (6)
C24—C25—H25A	120.1	C9—C8—H8A	120.0
C26—C25—H25A	120.1	C7—C8—H8A	120.0
C27—C26—C25	121.8 (6)	C8—C9—C10	122.5 (6)
C27—C26—H26A	119.1	C8—C9—H9A	118.8
C25—C26—H26A	119.1	C10—C9—H9A	118.8
C27—C28—C19	125.2 (6)	C9—C10—C1	126.1 (6)
C27—C28—C23	119.5 (6)	C9—C10—C5	117.8 (5)
C19—C28—C23	115.3 (6)	C1—C10—C5	116.1 (6)
O3—C29—N3	120.2 (5)	O2—C11—N1	121.6 (5)
O3—C29—C22	123.2 (5)	O2—C11—C6	122.4 (5)
N3—C29—C22	116.6 (5)	N1—C11—C6	116.0 (5)
O4—C30—N3	120.6 (5)	O1—C12—N1	119.9 (5)
O4—C30—C24	123.1 (5)	O1—C12—C4	124.3 (5)
N3—C30—C24	116.3 (4)	N1—C12—C4	115.8 (5)
C32—C31—N4	111.0 (5)	C14—C13—N2	109.8 (5)
C32—C31—H31A	109.4	C14—C13—H13A	109.7
N4—C31—H31A	109.4	N2—C13—H13A	109.7
C32—C31—H31B	109.4	C14—C13—H13B	109.7
N4—C31—H31B	109.4	N2—C13—H13B	109.7
H31A—C31—H31B	108.0	H13A—C13—H13B	108.2
C33—C32—C31	179.0 (7)	C15—C14—C13	177.1 (9)
C32—C33—H33	180.0	C14—C15—H15	180.0
C35—C34—N4	112.8 (5)	C17—C16—N2	110.5 (5)
C35—C34—H34A	109.0	C17—C16—H16A	109.5
N4—C34—H34A	109.0	N2—C16—H16A	109.5
C35—C34—H34B	109.0	C17—C16—H16B	109.5
N4—C34—H34B	109.0	N2—C16—H16B	109.5
H34A—C34—H34B	107.8	H16A—C16—H16B	108.1
C36—C35—C34	178.3 (7)	C18—C17—C16	178.6 (7)
C35—C36—H36	180.0	C17—C18—H18	180.0

C29—N3—N4—C34	62.9 (6)	C12—N1—N2—C16	58.3 (6)
C30—N3—N4—C34	−116.9 (5)	C11—N1—N2—C16	−121.7 (5)
C29—N3—N4—C31	−66.0 (6)	C12—N1—N2—C13	−72.5 (6)
C30—N3—N4—C31	114.2 (5)	C11—N1—N2—C13	107.6 (5)
C28—C19—C20—C21	−1.4 (10)	C10—C1—C2—C3	0.8 (9)
Br2—C19—C20—C21	178.6 (5)	Br1—C1—C2—C3	−179.7 (4)
C19—C20—C21—C22	1.2 (10)	C1—C2—C3—C4	−1.4 (9)
C20—C21—C22—C23	−1.3 (9)	C2—C3—C4—C5	0.3 (8)
C20—C21—C22—C29	−178.4 (5)	C2—C3—C4—C12	179.4 (5)
C21—C22—C23—C24	179.9 (5)	C3—C4—C5—C6	−179.2 (5)
C29—C22—C23—C24	−3.1 (8)	C12—C4—C5—C6	1.8 (7)
C21—C22—C23—C28	1.5 (8)	C3—C4—C5—C10	1.3 (8)
C29—C22—C23—C28	178.5 (5)	C12—C4—C5—C10	−177.8 (5)
C22—C23—C24—C25	−179.8 (5)	C4—C5—C6—C7	−177.7 (5)
C28—C23—C24—C25	−1.4 (7)	C10—C5—C6—C7	1.8 (7)
C22—C23—C24—C30	−0.1 (7)	C4—C5—C6—C11	3.8 (7)
C28—C23—C24—C30	178.3 (5)	C10—C5—C6—C11	−176.7 (4)
C23—C24—C25—C26	1.1 (8)	C5—C6—C7—C8	−0.5 (8)
C30—C24—C25—C26	−178.5 (5)	C11—C6—C7—C8	178.1 (5)
C28—C27—C26—C25	0.4 (9)	C6—C7—C8—C9	−1.3 (9)
C24—C25—C26—C27	−0.6 (9)	C7—C8—C9—C10	1.7 (9)
C26—C27—C28—C19	−179.5 (6)	C8—C9—C10—C1	179.6 (6)
C26—C27—C28—C23	−0.6 (9)	C8—C9—C10—C5	−0.3 (8)
C20—C19—C28—C27	−179.6 (6)	C2—C1—C10—C9	−179.1 (6)
Br2—C19—C28—C27	0.5 (8)	Br1—C1—C10—C9	1.5 (8)
C20—C19—C28—C23	1.5 (9)	C2—C1—C10—C5	0.8 (8)
Br2—C19—C28—C23	−178.4 (4)	Br1—C1—C10—C5	−178.7 (4)
C24—C23—C28—C27	1.1 (8)	C6—C5—C10—C9	−1.5 (7)
C22—C23—C28—C27	179.5 (5)	C4—C5—C10—C9	178.1 (5)
C24—C23—C28—C19	−179.9 (5)	C6—C5—C10—C1	178.7 (5)
C22—C23—C28—C19	−1.5 (7)	C4—C5—C10—C1	−1.8 (7)
N4—N3—C29—O3	1.8 (8)	C12—N1—C11—O2	174.4 (5)
C30—N3—C29—O3	−178.4 (5)	N2—N1—C11—O2	−5.6 (7)
N4—N3—C29—C22	−177.6 (4)	C12—N1—C11—C6	−4.6 (7)
C30—N3—C29—C22	2.2 (7)	N2—N1—C11—C6	175.3 (4)
C21—C22—C29—O3	−0.2 (8)	C7—C6—C11—O2	−0.2 (8)
C23—C22—C29—O3	−177.3 (5)	C5—C6—C11—O2	178.4 (5)
C21—C22—C29—N3	179.2 (5)	C7—C6—C11—N1	178.9 (5)
C23—C22—C29—N3	2.1 (7)	C5—C6—C11—N1	−2.5 (7)
C29—N3—C30—O4	175.9 (5)	C11—N1—C12—O1	−170.7 (5)
N4—N3—C30—O4	−4.4 (7)	N2—N1—C12—O1	9.4 (8)
C29—N3—C30—C24	−5.1 (7)	C11—N1—C12—C4	9.8 (7)
N4—N3—C30—C24	174.6 (4)	N2—N1—C12—C4	−170.1 (4)
C25—C24—C30—O4	2.6 (8)	C3—C4—C12—O1	−6.8 (9)
C23—C24—C30—O4	−177.0 (5)	C5—C4—C12—O1	172.3 (5)
C25—C24—C30—N3	−176.3 (5)	C3—C4—C12—N1	172.8 (5)
C23—C24—C30—N3	4.0 (7)	C5—C4—C12—N1	−8.2 (7)
N3—N4—C31—C32	−51.7 (6)	N1—N2—C13—C14	−171.5 (5)
C34—N4—C31—C32	178.6 (5)	C16—N2—C13—C14	59.6 (7)
N4—C31—C32—C33	176 (100)	N2—C13—C14—C15	−99 (15)
N3—N4—C34—C35	51.8 (6)	N1—N2—C16—C17	55.8 (6)
C31—N4—C34—C35	−178.3 (5)	C13—N2—C16—C17	−175.6 (5)
N4—C34—C35—C36	−157 (25)	N2—C16—C17—C18	−52 (32)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₁BrN₂O₂
M_r	367.20
Crystal system, space group	Triclinic, 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)
V (Å³)	1517.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.72
Crystal size (mm)	0.26 × 0.24 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.538, 0.640
No. of measured, independent and observed [I > 2σ(I)] reflections	8441, 5901, 3709
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.189, 1.04
No. of reflections	5901
No. of parameters	425
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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

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