2-(1H-Benzotriazol-1-yl)-1-(3-bromo­benzo­yl)ethyl benzoate

Hu, K.-C.; Wang, W.

doi:10.1107/S1600536809002608

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o392

doi:10.1107/S1600536809002608

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ADDENDA AND ERRATA

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2-(1H-Benzotriazol-1-yl)-1-(3-bromobenzoyl)ethyl benzoate

Kong-Cheng Hu ^a and Wei Wang ^a ^*

^aCollege of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, 210009 Nanjing, Jiangsu, People's Republic of China
^*Correspondence e-mail: wangwei9612@126.com

(Received 13 January 2009; accepted 21 January 2009; online 28 January 2009)

In the title compound, C₂₂H₁₆BrN₃O₃, the dihedral angles between the benzotriazole mean plane and the benzene rings of 4.84 (1) and 89.50 (1)°. The dihedral angle between the two benzene rings is 84.77 (1)°. In the crystal structure, molecules are linked into chains by intermolecular C—H⋯O hydrogen bonds. The crystal packing is further stabilized by C—H⋯π interactions.

Related literature

For general background on benzotriazoles, see: Xu et al. (2003 ). For the synthesis, see: Zhang et al. (2006 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₂H₁₆BrN₃O₃
M_r = 450.28
Triclinic, $[P \overline 1]$
a = 6.4390 (12) Å
b = 8.8267 (17) Å
c = 17.430 (3) Å
α = 88.589 (3)°
β = 85.024 (3)°
γ = 83.087 (3)°
V = 979.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.13 mm⁻¹
T = 293 (2) K
0.42 × 0.12 × 0.10 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.469, T_max = 0.815
5526 measured reflections
3773 independent reflections
2885 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.101
S = 1.04
3773 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1–N3/C17/C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯Cg1ⁱ	0.93	2.78	3.571	144
C21—H21A⋯O3ⁱⁱ	0.93	2.47	3.202 (4)	136
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002608/at2710sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002608/at2710Isup2.hkl

checkCIF report

Comment top

Benzotriazole derivatives have become the most efficient antifungal compounds with the properties of low toxicity, high oral bioavailability and so on (Xu et al., 2003). In order to search for new benzotriazole compounds with higher bioactivity, the title compound, (I), was synthesized, and its structure is presented here.

In the title compound (I) (Fig. 1), all bond lengths and angles are within normal ranges (Allen et al., 1987). The benzotriazole ring is essentially planar with a dihedral angle of 0.29 (15)°. The whole molecule is non-planar, with the dihedral angles between the benzotriazole mean plane and C1–C6 and C11–C16 benzene rings of 4.84 (1) and 89.50 (1)°, respectively. The dihedral angle between the two benzene rings is 84.77 (1)°.

In the crystal structure (Fig. 2), molecules are linked into chains along b axis by C21—H21A···O3 intermolecular hydrogen bonds (Table 1). Furthermore, the crystal packing is further stabilized by C—H···π interactions (Table 1).

Related literature top

For general background on benzotriazoles, see: Xu et al., (2003). For synthesis, see: Zhang et al. (2006). For bond-length data, see: Allen et al. (1987). [Please check rephrasing]

Experimental top

The title compound was prepared according to the literature method of Zhang et al. (2006). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of six days.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The structure of the compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. A packing diagram of (I), viewed down the a axis. Hydrogen bonds are indicated by dashed lines.

2-(1H-Benzotriazol-1-yl)-1-(3-bromobenzoyl)ethyl benzoate top

Crystal data top

C₂₂H₁₆BrN₃O₃	Z = 2
M_r = 450.28	F(000) = 456
Triclinic, P1	D_x = 1.527 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4390 (12) Å	Cell parameters from 2027 reflections
b = 8.8267 (17) Å	θ = 2.3–24.1°
c = 17.430 (3) Å	µ = 2.13 mm⁻¹
α = 88.589 (3)°	T = 293 K
β = 85.024 (3)°	Column, colourless
γ = 83.087 (3)°	0.42 × 0.12 × 0.10 mm
V = 979.6 (3) Å³

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3773 independent reflections
Radiation source: fine-focus sealed tube	2885 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.0°, θ_min = 2.3°
ω scans	h = −5→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→10
T_min = 0.469, T_max = 0.815	l = −21→21
5526 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0529P)² + 0.1162P] where P = (F_o² + 2F_c²)/3
3773 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₂H₁₆BrN₃O₃	γ = 83.087 (3)°
M_r = 450.28	V = 979.6 (3) Å³
Triclinic, P1	Z = 2
a = 6.4390 (12) Å	Mo Kα radiation
b = 8.8267 (17) Å	µ = 2.13 mm⁻¹
c = 17.430 (3) Å	T = 293 K
α = 88.589 (3)°	0.42 × 0.12 × 0.10 mm
β = 85.024 (3)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3773 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2885 reflections with I > 2σ(I)
T_min = 0.469, T_max = 0.815	R_int = 0.015
5526 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.04	Δρ_max = 0.45 e Å⁻³
3773 reflections	Δρ_min = −0.33 e Å⁻³
262 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
Br1	0.15134 (5)	0.67410 (4)	0.013609 (18)	0.07266 (15)
O1	0.8295 (3)	1.1006 (2)	−0.19239 (12)	0.0665 (5)
O2	0.6637 (3)	1.31723 (18)	−0.28399 (10)	0.0539 (5)
N2	0.0957 (4)	1.4833 (3)	−0.16528 (13)	0.0589 (6)
N1	0.2970 (3)	1.4981 (2)	−0.19112 (12)	0.0493 (5)
C3	0.2999 (4)	0.8086 (3)	−0.04996 (15)	0.0516 (6)
O3	0.6428 (4)	1.1121 (2)	−0.35433 (12)	0.0761 (6)
C17	0.3044 (4)	1.6208 (3)	−0.23960 (14)	0.0471 (6)
C7	0.6396 (4)	1.1190 (3)	−0.18590 (15)	0.0490 (6)
C4	0.5140 (4)	0.7794 (3)	−0.06486 (15)	0.0557 (7)
H4A	0.5862	0.6915	−0.0451	0.067*
C6	0.5140 (4)	1.0130 (3)	−0.13989 (14)	0.0471 (6)
C8	0.5243 (4)	1.2583 (3)	−0.22507 (15)	0.0499 (6)
H8A	0.3993	1.2305	−0.2470	0.060*
C2	0.1912 (4)	0.9376 (3)	−0.08071 (16)	0.0582 (7)
H2B	0.0461	0.9562	−0.0710	0.070*
C10	0.7238 (4)	1.2242 (3)	−0.34460 (15)	0.0544 (7)
C5	0.6206 (4)	0.8806 (3)	−0.10897 (15)	0.0535 (6)
H5A	0.7656	0.8612	−0.1185	0.064*
C18	0.0959 (4)	1.6813 (3)	−0.24132 (15)	0.0511 (6)
N3	−0.0275 (4)	1.5931 (3)	−0.19522 (14)	0.0624 (6)
C1	0.2975 (4)	1.0380 (3)	−0.12556 (16)	0.0560 (7)
H1A	0.2235	1.1238	−0.1466	0.067*
C9	0.4638 (4)	1.3866 (3)	−0.16730 (15)	0.0541 (6)
H9A	0.4194	1.3430	−0.1178	0.065*
H9B	0.5863	1.4376	−0.1608	0.065*
C22	0.4686 (5)	1.6847 (3)	−0.28088 (18)	0.0610 (7)
H22A	0.6080	1.6432	−0.2793	0.073*
C11	0.9024 (4)	1.2743 (3)	−0.39390 (15)	0.0535 (6)
C21	0.4115 (5)	1.8121 (3)	−0.3239 (2)	0.0726 (9)
H21A	0.5153	1.8587	−0.3526	0.087*
C19	0.0423 (5)	1.8118 (3)	−0.28590 (18)	0.0631 (8)
H19A	−0.0968	1.8536	−0.2879	0.076*
C12	0.9535 (6)	1.2079 (4)	−0.46490 (18)	0.0778 (9)
H12A	0.8719	1.1376	−0.4820	0.093*
C16	1.0265 (5)	1.3774 (4)	−0.36929 (18)	0.0721 (9)
H16A	0.9933	1.4227	−0.3215	0.086*
C20	0.2004 (6)	1.8749 (3)	−0.32606 (19)	0.0748 (9)
H20A	0.1688	1.9621	−0.3559	0.090*
C14	1.2476 (6)	1.3470 (5)	−0.4857 (2)	0.0931 (11)
H14A	1.3641	1.3710	−0.5169	0.112*
C15	1.1998 (6)	1.4135 (5)	−0.4154 (2)	0.0915 (11)
H15A	1.2835	1.4827	−0.3986	0.110*
C13	1.1247 (6)	1.2457 (5)	−0.5102 (2)	0.0958 (12)
H13A	1.1575	1.2017	−0.5583	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0764 (3)	0.0699 (2)	0.0733 (2)	−0.01787 (16)	−0.00824 (16)	0.01757 (16)
O1	0.0458 (12)	0.0633 (12)	0.0861 (14)	0.0045 (9)	−0.0008 (10)	0.0130 (10)
O2	0.0662 (12)	0.0404 (9)	0.0529 (11)	−0.0038 (8)	0.0035 (9)	−0.0007 (8)
N2	0.0512 (14)	0.0594 (14)	0.0609 (14)	0.0033 (11)	0.0100 (11)	0.0006 (11)
N1	0.0467 (12)	0.0456 (12)	0.0524 (12)	0.0060 (9)	−0.0012 (10)	−0.0012 (9)
C3	0.0587 (17)	0.0502 (15)	0.0470 (14)	−0.0080 (12)	−0.0096 (12)	0.0009 (11)
O3	0.1015 (17)	0.0571 (12)	0.0724 (14)	−0.0305 (12)	0.0110 (12)	−0.0155 (10)
C17	0.0480 (15)	0.0415 (13)	0.0508 (14)	0.0003 (11)	−0.0052 (11)	−0.0084 (11)
C7	0.0484 (16)	0.0452 (14)	0.0505 (15)	0.0058 (11)	−0.0038 (12)	−0.0022 (11)
C4	0.0607 (18)	0.0470 (15)	0.0564 (16)	0.0070 (12)	−0.0089 (13)	0.0052 (12)
C6	0.0468 (15)	0.0446 (14)	0.0477 (14)	0.0042 (11)	−0.0048 (11)	−0.0015 (11)
C8	0.0499 (15)	0.0448 (14)	0.0533 (15)	0.0007 (11)	−0.0031 (12)	0.0011 (11)
C2	0.0429 (15)	0.0668 (18)	0.0640 (17)	−0.0027 (13)	−0.0073 (13)	0.0078 (14)
C10	0.0697 (18)	0.0393 (14)	0.0529 (16)	−0.0020 (13)	−0.0046 (13)	−0.0002 (12)
C5	0.0464 (15)	0.0509 (15)	0.0597 (16)	0.0084 (12)	−0.0055 (12)	0.0009 (12)
C18	0.0504 (16)	0.0462 (14)	0.0551 (16)	0.0057 (12)	−0.0070 (12)	−0.0133 (12)
N3	0.0502 (14)	0.0616 (15)	0.0707 (16)	0.0059 (11)	0.0052 (12)	−0.0054 (12)
C1	0.0476 (16)	0.0549 (16)	0.0633 (17)	0.0046 (12)	−0.0095 (13)	0.0093 (13)
C9	0.0585 (16)	0.0489 (15)	0.0519 (15)	0.0098 (12)	−0.0093 (12)	−0.0006 (12)
C22	0.0541 (17)	0.0493 (16)	0.080 (2)	−0.0081 (13)	−0.0049 (14)	−0.0004 (14)
C11	0.0685 (18)	0.0447 (14)	0.0460 (14)	−0.0036 (12)	−0.0016 (12)	0.0014 (11)
C21	0.084 (2)	0.0511 (17)	0.085 (2)	−0.0206 (16)	−0.0047 (18)	0.0065 (15)
C19	0.0685 (19)	0.0480 (16)	0.0713 (19)	0.0103 (14)	−0.0190 (15)	−0.0072 (14)
C12	0.095 (2)	0.083 (2)	0.0592 (19)	−0.0282 (19)	0.0034 (17)	−0.0146 (17)
C16	0.083 (2)	0.075 (2)	0.0601 (18)	−0.0211 (17)	0.0040 (16)	−0.0129 (15)
C20	0.103 (3)	0.0417 (16)	0.081 (2)	0.0013 (16)	−0.0285 (19)	0.0060 (15)
C14	0.088 (3)	0.121 (3)	0.072 (2)	−0.034 (2)	0.017 (2)	−0.006 (2)
C15	0.093 (3)	0.105 (3)	0.082 (2)	−0.043 (2)	0.009 (2)	−0.017 (2)
C13	0.109 (3)	0.120 (3)	0.059 (2)	−0.035 (3)	0.021 (2)	−0.020 (2)

Geometric parameters (Å, º) top

Br1—C3	1.891 (3)	C5—H5A	0.9300
O1—C7	1.210 (3)	C18—N3	1.375 (4)
O2—C10	1.355 (3)	C18—C19	1.399 (4)
O2—C8	1.435 (3)	C1—H1A	0.9300
N2—N3	1.305 (3)	C9—H9A	0.9700
N2—N1	1.355 (3)	C9—H9B	0.9700
N1—C17	1.360 (3)	C22—C21	1.367 (4)
N1—C9	1.448 (3)	C22—H22A	0.9300
C3—C4	1.374 (4)	C11—C12	1.379 (4)
C3—C2	1.385 (4)	C11—C16	1.380 (4)
O3—C10	1.195 (3)	C21—C20	1.409 (5)
C17—C18	1.386 (4)	C21—H21A	0.9300
C17—C22	1.394 (4)	C19—C20	1.353 (4)
C7—C6	1.485 (4)	C19—H19A	0.9300
C7—C8	1.535 (3)	C12—C13	1.369 (5)
C4—C5	1.372 (4)	C12—H12A	0.9300
C4—H4A	0.9300	C16—C15	1.382 (4)
C6—C1	1.387 (4)	C16—H16A	0.9300
C6—C5	1.402 (3)	C20—H20A	0.9300
C8—C9	1.527 (4)	C14—C13	1.362 (5)
C8—H8A	0.9800	C14—C15	1.368 (5)
C2—C1	1.373 (4)	C14—H14A	0.9300
C2—H2B	0.9300	C15—H15A	0.9300
C10—C11	1.480 (4)	C13—H13A	0.9300

C10—O2—C8	115.31 (19)	C2—C1—C6	120.8 (2)
N3—N2—N1	108.8 (2)	C2—C1—H1A	119.6
N2—N1—C17	110.4 (2)	C6—C1—H1A	119.6
N2—N1—C9	119.2 (2)	N1—C9—C8	112.8 (2)
C17—N1—C9	130.4 (2)	N1—C9—H9A	109.0
C4—C3—C2	120.3 (2)	C8—C9—H9A	109.0
C4—C3—Br1	120.3 (2)	N1—C9—H9B	109.0
C2—C3—Br1	119.3 (2)	C8—C9—H9B	109.0
N1—C17—C18	103.9 (2)	H9A—C9—H9B	107.8
N1—C17—C22	133.2 (2)	C21—C22—C17	115.7 (3)
C18—C17—C22	122.9 (2)	C21—C22—H22A	122.1
O1—C7—C6	122.2 (2)	C17—C22—H22A	122.1
O1—C7—C8	119.0 (2)	C12—C11—C16	119.2 (3)
C6—C7—C8	118.8 (2)	C12—C11—C10	118.4 (3)
C5—C4—C3	119.7 (2)	C16—C11—C10	122.3 (2)
C5—C4—H4A	120.1	C22—C21—C20	122.1 (3)
C3—C4—H4A	120.1	C22—C21—H21A	119.0
C1—C6—C5	118.3 (2)	C20—C21—H21A	119.0
C1—C6—C7	123.6 (2)	C20—C19—C18	117.5 (3)
C5—C6—C7	118.1 (2)	C20—C19—H19A	121.2
O2—C8—C9	105.9 (2)	C18—C19—H19A	121.2
O2—C8—C7	109.4 (2)	C13—C12—C11	119.9 (3)
C9—C8—C7	110.1 (2)	C13—C12—H12A	120.1
O2—C8—H8A	110.4	C11—C12—H12A	120.1
C9—C8—H8A	110.4	C11—C16—C15	120.3 (3)
C7—C8—H8A	110.4	C11—C16—H16A	119.9
C1—C2—C3	120.0 (2)	C15—C16—H16A	119.9
C1—C2—H2B	120.0	C19—C20—C21	121.7 (3)
C3—C2—H2B	120.0	C19—C20—H20A	119.1
O3—C10—O2	122.4 (2)	C21—C20—H20A	119.1
O3—C10—C11	125.0 (2)	C13—C14—C15	120.0 (3)
O2—C10—C11	112.5 (2)	C13—C14—H14A	120.0
C4—C5—C6	121.0 (2)	C15—C14—H14A	120.0
C4—C5—H5A	119.5	C14—C15—C16	119.7 (3)
C6—C5—H5A	119.5	C14—C15—H15A	120.1
N3—C18—C17	109.1 (2)	C16—C15—H15A	120.1
N3—C18—C19	130.8 (3)	C14—C13—C12	120.9 (3)
C17—C18—C19	120.1 (3)	C14—C13—H13A	119.5
N2—N3—C18	107.9 (2)	C12—C13—H13A	119.5

N3—N2—N1—C17	−0.3 (3)	N1—N2—N3—C18	−0.2 (3)
N3—N2—N1—C9	−178.5 (2)	C17—C18—N3—N2	0.5 (3)
N2—N1—C17—C18	0.6 (3)	C19—C18—N3—N2	−179.8 (3)
C9—N1—C17—C18	178.5 (2)	C3—C2—C1—C6	−0.8 (4)
N2—N1—C17—C22	−180.0 (3)	C5—C6—C1—C2	1.6 (4)
C9—N1—C17—C22	−2.0 (5)	C7—C6—C1—C2	−178.1 (3)
C2—C3—C4—C5	1.5 (4)	N2—N1—C9—C8	94.5 (3)
Br1—C3—C4—C5	−177.8 (2)	C17—N1—C9—C8	−83.3 (3)
O1—C7—C6—C1	174.0 (3)	O2—C8—C9—N1	81.7 (3)
C8—C7—C6—C1	−4.7 (4)	C7—C8—C9—N1	−160.1 (2)
O1—C7—C6—C5	−5.7 (4)	N1—C17—C22—C21	−179.5 (3)
C8—C7—C6—C5	175.6 (2)	C18—C17—C22—C21	−0.1 (4)
C10—O2—C8—C9	−175.1 (2)	O3—C10—C11—C12	14.4 (4)
C10—O2—C8—C7	66.3 (3)	O2—C10—C11—C12	−167.9 (3)
O1—C7—C8—O2	18.8 (3)	O3—C10—C11—C16	−161.4 (3)
C6—C7—C8—O2	−162.4 (2)	O2—C10—C11—C16	16.3 (4)
O1—C7—C8—C9	−97.1 (3)	C17—C22—C21—C20	0.2 (5)
C6—C7—C8—C9	81.6 (3)	N3—C18—C19—C20	−179.9 (3)
C4—C3—C2—C1	−0.8 (4)	C17—C18—C19—C20	−0.3 (4)
Br1—C3—C2—C1	178.6 (2)	C16—C11—C12—C13	−0.5 (5)
C8—O2—C10—O3	10.9 (4)	C10—C11—C12—C13	−176.5 (3)
C8—O2—C10—C11	−166.9 (2)	C12—C11—C16—C15	0.0 (5)
C3—C4—C5—C6	−0.7 (4)	C10—C11—C16—C15	175.8 (3)
C1—C6—C5—C4	−0.8 (4)	C18—C19—C20—C21	0.4 (5)
C7—C6—C5—C4	178.9 (2)	C22—C21—C20—C19	−0.4 (5)
N1—C17—C18—N3	−0.7 (3)	C13—C14—C15—C16	0.0 (7)
C22—C17—C18—N3	179.8 (2)	C11—C16—C15—C14	0.3 (6)
N1—C17—C18—C19	179.6 (2)	C15—C14—C13—C12	−0.5 (7)
C22—C17—C18—C19	0.1 (4)	C11—C12—C13—C14	0.8 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···Cg1ⁱ	0.93	2.78	3.571	144
C21—H21A···O3ⁱⁱ	0.93	2.47	3.202 (4)	136

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆BrN₃O₃
M_r	450.28
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.4390 (12), 8.8267 (17), 17.430 (3)
α, β, γ (°)	88.589 (3), 85.024 (3), 83.087 (3)
V (Å³)	979.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.13
Crystal size (mm)	0.42 × 0.12 × 0.10

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.469, 0.815
No. of measured, independent and observed [I > 2σ(I)] reflections	5526, 3773, 2885
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.101, 1.04
No. of reflections	3773
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.33

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···Cg1ⁱ	0.93	2.778	3.571	143.94
C21—H21A···O3ⁱⁱ	0.93	2.472	3.202 (4)	135.50

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

Acknowledgements

This project was supported by the Natural Science Foundation of Shandong Province (grant Nos. Y2008B02 and Y2008B32).

References

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