2-(1H-Benzotriazol-1-yl)-1-(4-bromo­benzo­yl)ethyl 4-methyl­benzoate

Sun, J.-L.; Wang, M.; Zhu, Y.-J.; Li, F.; Bi, S.

doi:10.1107/S1600536807062587

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o122

https://doi.org/10.1107/S1600536807062587

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2-(1H-Benzotriazol-1-yl)-1-(4-bromobenzoyl)ethyl 4-methylbenzoate

Jiu-Long Sun,^a Meng Wang,^a Ying-Jie Zhu,^a Fang Li ^a and Sai Bi ^a ^*

^aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, 266042 Qingdao, Shandong, People's Republic of China
^*Correspondence e-mail: qustchemistry@126.com

(Received 21 November 2007; accepted 23 November 2007; online 6 December 2007)

In the molecule of the title compound, C₂₃H₁₈BrN₃O₃, the benzotriazole mean plane makes dihedral angles of 1.26 (1) and 87.39 (1)° with the tolyl and bromophenyl benzene rings, respectively, and the dihedral angle between the benzene rings is 87.27 (1)°. In the crystal structure, molecules are linked into chains along the a axis by C—H⋯O intermolecular hydrogen bonds. The structure is further stabilized by C—H⋯π and π–π interactions, with a distance of 3.700 (1) Å between the centroids of the bromophenyl and benzotriazole benzene rings related by symmetry code (x, −1 + y, z).

Related literature

For related literature, see: Wan et al. (2006 ). For reference structural data, see Allen et al., (1987 ).

Experimental

Crystal data

C₂₃H₁₈BrN₃O₃
M_r = 464.30
Triclinic, $[P \overline 1]$
a = 6.995 (2) Å
b = 9.038 (2) Å
c = 16.909 (5) Å
α = 87.617 (5)°
β = 85.741 (5)°
γ = 74.688 (5)°
V = 1027.8 (5) Å³
Z = 2
Mo Kα radiation
μ = 2.03 mm⁻¹
T = 293 (2) K
0.35 × 0.12 × 0.07 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.537, T_max = 0.871
5629 measured reflections
3814 independent reflections
2852 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.100
S = 1.01
3814 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.30 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
C15—H15A⋯Cg1ⁱ	0.93	2.86	3.596 (1)	138
C2—H2A⋯O1ⁱⁱ	0.93	2.56	3.292 (4)	137
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807062587/at2508sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062587/at2508Isup2.hkl

checkCIF report

Comment top

Recently, we have reported the structure of 2-(1H-1,2,3-benzotriazol-1-ylmethyl)-1-benzoylethyl 4-chlorobenzoate (II) (Wan et al., 2006). As part of our ongoing studies on new benzotriazole derivatives with higher bioactivity, the title compound, (I), was synthesized and its structure is presented here.

In the molecule of (I), all bond lengths and angles are within normal ranges (Allen et al., 1987) and are comparable with those in the related compound, (II). The benzotriazole system is essentially planar with a dihedral angle of 1.14 (2)° between the N1–N3/C17/C18 triazole ring and C17–C22 benzene ring. The benzotriazole mean plane makes dihedral angles of 1.26 (1)° and 87.39 (1)°, respectively, with the two benzene rings C1–C6 and C11–C16. The dihedral angle between the benzene rings is 87.27 (1)°.

In the crystal structure (Fig. 2), intermolecular C1—H2A···O1 hydrogen bonds (Table 1) link the molecules into infinite chains along the a axis. The molecules are further stabilized by C—H···π interactions (Table 1). The distance of 3.700 (1) Å between the centroids of benzene rings C1–C6 and C17–C22 related by symmetry code (x, -1 + y, z) suggests a possible π–π interactions.

Related literature top

For related literature, see: Wan et al. (2006). For reference structural data, see Allen et al., (1987).

Experimental top

The title compound was prepared according to the literature method of Wan 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 a week.

Structure description top

For related literature, see: Wan et al. (2006). For reference structural data, see Allen et al., (1987).

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, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b), 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 b axis. Hydrogen bonds are indicated by dashed lines.

2-(1H-Benzotriazol-1-yl)-1-(4-bromobenzoyl)ethyl 4-methylbenzoate top

Crystal data top

C₂₃H₁₈BrN₃O₃	Z = 2
M_r = 464.30	F(000) = 472
Triclinic, P1	D_x = 1.500 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.995 (2) Å	Cell parameters from 1830 reflections
b = 9.038 (2) Å	θ = 2.4–22.9°
c = 16.909 (5) Å	µ = 2.03 mm⁻¹
α = 87.617 (5)°	T = 293 K
β = 85.741 (5)°	Block, colourless
γ = 74.688 (5)°	0.35 × 0.12 × 0.07 mm
V = 1027.8 (5) Å³

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3814 independent reflections
Radiation source: fine-focus sealed tube	2852 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
Detector resolution: 8.33 pixels mm^-1	θ_max = 25.7°, θ_min = 2.3°
ω scans	h = −8→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
T_min = 0.537, T_max = 0.871	l = −20→16
5629 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0475P)² + 0.3285P] where P = (F_o² + 2F_c²)/3
3814 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₃H₁₈BrN₃O₃	γ = 74.688 (5)°
M_r = 464.30	V = 1027.8 (5) Å³
Triclinic, P1	Z = 2
a = 6.995 (2) Å	Mo Kα radiation
b = 9.038 (2) Å	µ = 2.03 mm⁻¹
c = 16.909 (5) Å	T = 293 K
α = 87.617 (5)°	0.35 × 0.12 × 0.07 mm
β = 85.741 (5)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3814 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2852 reflections with I > 2σ(I)
T_min = 0.537, T_max = 0.871	R_int = 0.016
5629 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.01	Δρ_max = 0.40 e Å⁻³
3814 reflections	Δρ_min = −0.30 e Å⁻³
271 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	0.64770 (5)	0.65794 (4)	0.01583 (2)	0.06665 (16)
O2	1.0846 (3)	1.2940 (2)	−0.26852 (11)	0.0472 (5)
N1	0.7376 (3)	1.5016 (3)	−0.18983 (14)	0.0455 (6)
O3	1.0928 (3)	1.1006 (2)	−0.34871 (13)	0.0603 (6)
O1	1.2452 (3)	1.0717 (3)	−0.16910 (15)	0.0699 (7)
C2	0.6600 (4)	0.9193 (3)	−0.08211 (18)	0.0488 (7)
H2A	0.5225	0.9380	−0.0802	0.059*
C3	0.7730 (4)	0.7930 (3)	−0.04374 (17)	0.0453 (7)
C7	1.0667 (4)	1.0962 (3)	−0.16942 (17)	0.0470 (7)
C6	0.9582 (4)	0.9930 (3)	−0.12617 (16)	0.0415 (7)
C17	0.7777 (4)	1.6225 (3)	−0.23346 (17)	0.0413 (7)
C10	1.1583 (4)	1.2049 (3)	−0.33201 (17)	0.0445 (7)
C4	0.9777 (4)	0.7610 (3)	−0.04786 (17)	0.0485 (7)
H4A	1.0529	0.6727	−0.0237	0.058*
N2	0.5383 (4)	1.5173 (3)	−0.18266 (17)	0.0586 (7)
N3	0.4501 (4)	1.6420 (3)	−0.22037 (18)	0.0634 (8)
C8	0.9513 (4)	1.2398 (3)	−0.21355 (17)	0.0448 (7)
H8A	0.8438	1.2177	−0.2410	0.054*
C1	0.7540 (4)	1.0183 (3)	−0.12364 (18)	0.0479 (7)
H1A	0.6786	1.1034	−0.1503	0.057*
C5	1.0687 (4)	0.8622 (3)	−0.08842 (17)	0.0482 (7)
H5A	1.2064	0.8425	−0.0905	0.058*
C11	1.3249 (4)	1.2494 (3)	−0.37556 (16)	0.0417 (7)
C18	0.5918 (4)	1.7106 (3)	−0.25259 (18)	0.0484 (7)
C14	1.6529 (5)	1.3212 (4)	−0.45817 (19)	0.0539 (8)
C9	0.8691 (4)	1.3685 (3)	−0.15506 (17)	0.0485 (7)
H9A	0.7980	1.3305	−0.1107	0.058*
H9B	0.9790	1.3984	−0.1346	0.058*
C22	0.9514 (4)	1.6647 (3)	−0.25652 (19)	0.0510 (8)
H22A	1.0754	1.6052	−0.2432	0.061*
C15	1.5886 (5)	1.3755 (4)	−0.3833 (2)	0.0581 (8)
H15A	1.6554	1.4369	−0.3599	0.070*
C21	0.9294 (6)	1.7981 (4)	−0.2997 (2)	0.0640 (9)
H21A	1.0418	1.8309	−0.3157	0.077*
C13	1.5503 (5)	1.2311 (4)	−0.49113 (19)	0.0620 (9)
H13A	1.5903	1.1943	−0.5419	0.074*
C16	1.4265 (5)	1.3409 (4)	−0.34183 (19)	0.0538 (8)
H16A	1.3859	1.3791	−0.2914	0.065*
C12	1.3898 (5)	1.1939 (4)	−0.45095 (19)	0.0556 (8)
H12A	1.3247	1.1314	−0.4744	0.067*
C19	0.5745 (6)	1.8472 (4)	−0.2986 (2)	0.0635 (9)
H19A	0.4518	1.9070	−0.3131	0.076*
C20	0.7445 (6)	1.8872 (4)	−0.3207 (2)	0.0700 (10)
H20A	0.7376	1.9768	−0.3507	0.084*
C23	1.8288 (5)	1.3588 (4)	−0.5021 (2)	0.0748 (11)
H23A	1.8520	1.3110	−0.5529	0.112*
H23B	1.9438	1.3214	−0.4721	0.112*
H23C	1.8032	1.4680	−0.5096	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0657 (3)	0.0510 (2)	0.0827 (3)	−0.01976 (17)	0.00767 (18)	0.01260 (17)
O2	0.0511 (12)	0.0408 (10)	0.0493 (12)	−0.0145 (9)	0.0068 (10)	0.0008 (9)
N1	0.0372 (14)	0.0429 (13)	0.0534 (15)	−0.0059 (11)	0.0009 (11)	−0.0022 (11)
O3	0.0652 (15)	0.0523 (13)	0.0687 (15)	−0.0269 (12)	0.0071 (12)	−0.0078 (11)
O1	0.0403 (14)	0.0751 (16)	0.0899 (18)	−0.0122 (11)	−0.0056 (12)	0.0310 (13)
C2	0.0351 (16)	0.0505 (17)	0.0577 (19)	−0.0072 (14)	−0.0024 (14)	0.0071 (15)
C3	0.0519 (19)	0.0412 (16)	0.0441 (17)	−0.0149 (14)	−0.0020 (14)	0.0012 (13)
C7	0.0394 (18)	0.0489 (17)	0.0500 (18)	−0.0084 (14)	0.0004 (14)	0.0043 (14)
C6	0.0401 (17)	0.0398 (15)	0.0419 (16)	−0.0064 (13)	−0.0020 (13)	0.0027 (13)
C17	0.0414 (17)	0.0361 (14)	0.0448 (17)	−0.0059 (13)	−0.0055 (13)	−0.0047 (12)
C10	0.0472 (18)	0.0363 (15)	0.0476 (17)	−0.0076 (14)	−0.0043 (14)	0.0067 (13)
C4	0.0449 (18)	0.0449 (17)	0.0495 (18)	−0.0018 (14)	−0.0060 (14)	0.0103 (14)
N2	0.0386 (15)	0.0616 (17)	0.0748 (19)	−0.0141 (13)	0.0098 (13)	−0.0108 (15)
N3	0.0378 (15)	0.0599 (18)	0.088 (2)	−0.0039 (14)	−0.0047 (15)	−0.0086 (16)
C8	0.0415 (17)	0.0447 (16)	0.0475 (17)	−0.0123 (13)	0.0012 (13)	0.0077 (13)
C1	0.0406 (17)	0.0445 (16)	0.0519 (18)	−0.0009 (13)	−0.0042 (14)	0.0089 (14)
C5	0.0363 (17)	0.0526 (18)	0.0518 (18)	−0.0051 (14)	−0.0052 (14)	0.0059 (14)
C11	0.0437 (17)	0.0367 (14)	0.0414 (16)	−0.0061 (13)	0.0005 (13)	0.0037 (12)
C18	0.0424 (18)	0.0449 (17)	0.0557 (19)	−0.0047 (14)	−0.0084 (14)	−0.0105 (14)
C14	0.0472 (19)	0.0560 (19)	0.055 (2)	−0.0107 (15)	0.0015 (15)	0.0099 (16)
C9	0.0479 (18)	0.0498 (17)	0.0435 (17)	−0.0075 (14)	0.0012 (14)	0.0056 (14)
C22	0.0407 (18)	0.0485 (17)	0.064 (2)	−0.0119 (14)	−0.0001 (15)	−0.0044 (15)
C15	0.056 (2)	0.060 (2)	0.064 (2)	−0.0253 (17)	−0.0023 (17)	−0.0009 (17)
C21	0.068 (2)	0.053 (2)	0.074 (2)	−0.0241 (18)	0.0064 (19)	−0.0016 (17)
C13	0.070 (2)	0.070 (2)	0.0427 (19)	−0.0167 (19)	0.0139 (16)	−0.0045 (16)
C16	0.055 (2)	0.0575 (19)	0.0499 (19)	−0.0171 (16)	0.0015 (15)	−0.0021 (15)
C12	0.066 (2)	0.0507 (18)	0.052 (2)	−0.0197 (16)	0.0011 (16)	−0.0063 (15)
C19	0.070 (2)	0.0463 (19)	0.067 (2)	0.0044 (17)	−0.0256 (19)	−0.0064 (16)
C20	0.098 (3)	0.0427 (18)	0.067 (2)	−0.013 (2)	−0.010 (2)	0.0054 (17)
C23	0.055 (2)	0.092 (3)	0.074 (3)	−0.020 (2)	0.0084 (19)	0.022 (2)

Geometric parameters (Å, º) top

Br1—C3	1.898 (3)	C5—H5A	0.9300
O2—C10	1.355 (3)	C11—C16	1.387 (4)
O2—C8	1.431 (3)	C11—C12	1.389 (4)
N1—N2	1.360 (3)	C18—C19	1.415 (5)
N1—C17	1.371 (3)	C14—C13	1.377 (5)
N1—C9	1.441 (4)	C14—C15	1.378 (4)
O3—C10	1.203 (3)	C14—C23	1.498 (4)
O1—C7	1.209 (3)	C9—H9A	0.9700
C2—C3	1.374 (4)	C9—H9B	0.9700
C2—C1	1.385 (4)	C22—C21	1.362 (4)
C2—H2A	0.9300	C22—H22A	0.9300
C3—C4	1.381 (4)	C15—C16	1.388 (4)
C7—C6	1.488 (4)	C15—H15A	0.9300
C7—C8	1.533 (4)	C21—C20	1.393 (5)
C6—C1	1.383 (4)	C21—H21A	0.9300
C6—C5	1.390 (4)	C13—C12	1.379 (4)
C17—C18	1.387 (4)	C13—H13A	0.9300
C17—C22	1.391 (4)	C16—H16A	0.9300
C10—C11	1.469 (4)	C12—H12A	0.9300
C4—C5	1.379 (4)	C19—C20	1.353 (5)
C4—H4A	0.9300	C19—H19A	0.9300
N2—N3	1.299 (4)	C20—H20A	0.9300
N3—C18	1.371 (4)	C23—H23A	0.9600
C8—C9	1.523 (4)	C23—H23B	0.9600
C8—H8A	0.9800	C23—H23C	0.9600
C1—H1A	0.9300

C10—O2—C8	116.1 (2)	N3—C18—C17	109.1 (3)
N2—N1—C17	110.0 (2)	N3—C18—C19	131.0 (3)
N2—N1—C9	119.3 (2)	C17—C18—C19	119.9 (3)
C17—N1—C9	130.7 (2)	C13—C14—C15	117.7 (3)
C3—C2—C1	119.0 (3)	C13—C14—C23	121.2 (3)
C3—C2—H2A	120.5	C15—C14—C23	121.1 (3)
C1—C2—H2A	120.5	N1—C9—C8	113.1 (2)
C2—C3—C4	121.3 (3)	N1—C9—H9A	109.0
C2—C3—Br1	119.9 (2)	C8—C9—H9A	109.0
C4—C3—Br1	118.8 (2)	N1—C9—H9B	109.0
O1—C7—C6	121.5 (3)	C8—C9—H9B	109.0
O1—C7—C8	118.6 (3)	H9A—C9—H9B	107.8
C6—C7—C8	119.9 (2)	C21—C22—C17	116.2 (3)
C1—C6—C5	118.5 (3)	C21—C22—H22A	121.9
C1—C6—C7	123.4 (3)	C17—C22—H22A	121.9
C5—C6—C7	118.1 (3)	C14—C15—C16	121.6 (3)
N1—C17—C18	103.8 (2)	C14—C15—H15A	119.2
N1—C17—C22	133.8 (3)	C16—C15—H15A	119.2
C18—C17—C22	122.5 (3)	C22—C21—C20	122.4 (3)
O3—C10—O2	122.3 (3)	C22—C21—H21A	118.8
O3—C10—C11	125.2 (3)	C20—C21—H21A	118.8
O2—C10—C11	112.5 (2)	C14—C13—C12	121.8 (3)
C5—C4—C3	119.0 (3)	C14—C13—H13A	119.1
C5—C4—H4A	120.5	C12—C13—H13A	119.1
C3—C4—H4A	120.5	C11—C16—C15	120.1 (3)
N3—N2—N1	108.7 (2)	C11—C16—H16A	119.9
N2—N3—C18	108.5 (2)	C15—C16—H16A	119.9
O2—C8—C9	105.7 (2)	C13—C12—C11	120.2 (3)
O2—C8—C7	109.4 (2)	C13—C12—H12A	119.9
C9—C8—C7	109.5 (2)	C11—C12—H12A	119.9
O2—C8—H8A	110.7	C20—C19—C18	117.1 (3)
C9—C8—H8A	110.7	C20—C19—H19A	121.4
C7—C8—H8A	110.7	C18—C19—H19A	121.4
C6—C1—C2	121.2 (3)	C19—C20—C21	122.0 (3)
C6—C1—H1A	119.4	C19—C20—H20A	119.0
C2—C1—H1A	119.4	C21—C20—H20A	119.0
C4—C5—C6	121.1 (3)	C14—C23—H23A	109.5
C4—C5—H5A	119.5	C14—C23—H23B	109.5
C6—C5—H5A	119.5	H23A—C23—H23B	109.5
C16—C11—C12	118.5 (3)	C14—C23—H23C	109.5
C16—C11—C10	121.5 (3)	H23A—C23—H23C	109.5
C12—C11—C10	119.9 (3)	H23B—C23—H23C	109.5

C1—C2—C3—C4	−1.9 (5)	O2—C10—C11—C16	17.0 (4)
C1—C2—C3—Br1	178.4 (2)	O3—C10—C11—C12	14.9 (5)
O1—C7—C6—C1	178.7 (3)	O2—C10—C11—C12	−166.0 (3)
C8—C7—C6—C1	0.5 (4)	N2—N3—C18—C17	0.0 (4)
O1—C7—C6—C5	−3.3 (5)	N2—N3—C18—C19	−179.9 (3)
C8—C7—C6—C5	178.6 (3)	N1—C17—C18—N3	0.3 (3)
N2—N1—C17—C18	−0.5 (3)	C22—C17—C18—N3	−178.6 (3)
C9—N1—C17—C18	177.8 (3)	N1—C17—C18—C19	−179.7 (3)
N2—N1—C17—C22	178.2 (3)	C22—C17—C18—C19	1.4 (4)
C9—N1—C17—C22	−3.5 (5)	N2—N1—C9—C8	94.9 (3)
C8—O2—C10—O3	11.8 (4)	C17—N1—C9—C8	−83.2 (4)
C8—O2—C10—C11	−167.4 (2)	O2—C8—C9—N1	69.6 (3)
C2—C3—C4—C5	3.0 (5)	C7—C8—C9—N1	−172.6 (2)
Br1—C3—C4—C5	−177.4 (2)	N1—C17—C22—C21	−178.8 (3)
C17—N1—N2—N3	0.6 (3)	C18—C17—C22—C21	−0.3 (4)
C9—N1—N2—N3	−178.0 (3)	C13—C14—C15—C16	0.2 (5)
N1—N2—N3—C18	−0.4 (3)	C23—C14—C15—C16	−179.7 (3)
C10—O2—C8—C9	−172.5 (2)	C17—C22—C21—C20	−0.7 (5)
C10—O2—C8—C7	69.6 (3)	C15—C14—C13—C12	−0.8 (5)
O1—C7—C8—O2	18.9 (4)	C23—C14—C13—C12	179.1 (3)
C6—C7—C8—O2	−163.0 (2)	C12—C11—C16—C15	0.2 (5)
O1—C7—C8—C9	−96.6 (3)	C10—C11—C16—C15	177.3 (3)
C6—C7—C8—C9	81.6 (3)	C14—C15—C16—C11	0.1 (5)
C5—C6—C1—C2	2.4 (5)	C14—C13—C12—C11	1.1 (5)
C7—C6—C1—C2	−179.6 (3)	C16—C11—C12—C13	−0.7 (5)
C3—C2—C1—C6	−0.8 (5)	C10—C11—C12—C13	−177.9 (3)
C3—C4—C5—C6	−1.3 (5)	N3—C18—C19—C20	178.6 (3)
C1—C6—C5—C4	−1.3 (4)	C17—C18—C19—C20	−1.4 (5)
C7—C6—C5—C4	−179.4 (3)	C18—C19—C20—C21	0.4 (5)
O3—C10—C11—C16	−162.2 (3)	C22—C21—C20—C19	0.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···Cg1ⁱ	0.93	2.86	3.596 (1)	138
C2—H2A···O1ⁱⁱ	0.93	2.56	3.292 (4)	137

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₈BrN₃O₃
M_r	464.30
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.995 (2), 9.038 (2), 16.909 (5)
α, β, γ (°)	87.617 (5), 85.741 (5), 74.688 (5)
V (Å³)	1027.8 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.03
Crystal size (mm)	0.35 × 0.12 × 0.07

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.537, 0.871
No. of measured, independent and observed [I > 2σ(I)] reflections	5629, 3814, 2852
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.100, 1.01
No. of reflections	3814
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.30

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), 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
C15—H15A···Cg1ⁱ	0.93	2.855	3.596 (1)	137.50
C2—H2A···O1ⁱⁱ	0.93	2.555	3.292 (4)	136.45

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

Acknowledgements

This project was supported by the Natural Science Foundation of Shandong Province (grant Nos. Z2006B01 and Y2006B07).

References

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. CSD CrossRef Web of Science Google Scholar
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