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

Hu, K.-C.; Li, G.-J.

doi:10.1107/S1600536809002712

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o443

doi:10.1107/S1600536809002712

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

Kong-Cheng Hu ^a and Guang-Jiu Li ^a ^*

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

(Received 14 January 2009; accepted 22 January 2009; online 31 January 2009)

In the title compound, C₂₂H₁₅BrClN₃O₃, the benzotriazole ring system makes dihedral angles of 2.43 (1) and 71.51 (1)° with the bromophenyl and chlorophenyl rings, respectively; the angle between the latter two rings is 69.26 (1)°. In the crystal structure, molecules are linked into chains by intermolecular C—H⋯O hydrogen bonds. The crystal packing is further stabilized by π–π (with a centroid-centroid distance of 3.764 Å) and C—H⋯π interactions.

Related literature

For the crystal structure of a related compound, see: Zeng et al. (2007 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₂H₁₅BrClN₃O₃
M_r = 484.72
Monoclinic, P 2₁ /c
a = 6.2613 (7) Å
b = 36.688 (4) Å
c = 8.7919 (9) Å
β = 90.878 (2)°
V = 2019.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.20 mm⁻¹
T = 293 (2) K
0.36 × 0.21 × 0.09 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.505, T_max = 0.827
11039 measured reflections
3978 independent reflections
2968 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.103
S = 1.04
3978 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯Cg1ⁱ	0.93	2.87	3.707	150
C21—H21A⋯O3ⁱⁱ	0.93	2.47	3.101 (4)	126
Symmetry codes: (i) x-1, y, z; (ii) x, y, z+1.

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/S1600536809002712/wn2306sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002712/wn2306Isup2.hkl

checkCIF report

Comment top

The crystal structure of 2-(benzotriazol-1-yl)-1-(4-methylbenzoyl)ethyl 4-ethylbenzoate has been reported by Zeng et al. (2007). In a search for new benzotriazole derivatives with higher bioactivity, the title compound was synthesized and its structure is reported here.

In the title molecule (Fig. 1), all bond lengths (Allen et al., 1987) and angles are within normal ranges. The benzotriazole system is almost planar, with a dihedral angle of 0.89 (1)° between the triazole ring (N1–N3/C17/C18) and the benzene ring A (C17–C22). The benzotriazole mean plane makes dihedral angles of 2.43 (1)° and 71.51 (1)° with benzene rings B (C1–C6) and C (C11–C16), respectively, indicating the non-planarity of the whole molecule. The dihedral angle between rings B and C is 69.26 (1)°.

In the crystal structure (Fig. 2), molecules are linked into chains along the c axis by intermolecular C21—H21A···O3 hydrogen bonds (Table 1). The distance of 3.764 Å between the centroids of rings A and B related by the symmetry code (x, y, -1 + z) suggests a possible π···π interaction. The crystal packing is further stabilized by C—H···π interactions (Table 1).

Related literature top

For the crystal structure of a related compound, see: Zeng et al. (2007). For standard bond-length data, see: Allen et al., (1987).

Experimental top

The title compound was prepared according to the literature method of Zeng et al. (2007). 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 molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme. Hydrogen atoms are represented by spheres of arbitrary radius.
	Fig. 2. A packing diagram, viewed down the a axis. Hydrogen bonds are indicated by dashed lines.

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

Crystal data top

C₂₂H₁₅BrClN₃O₃	F(000) = 976
M_r = 484.72	D_x = 1.594 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.2613 (7) Å	Cell parameters from 3180 reflections
b = 36.688 (4) Å	θ = 2.2–22.9°
c = 8.7919 (9) Å	µ = 2.20 mm⁻¹
β = 90.878 (2)°	T = 293 K
V = 2019.4 (4) Å³	Plate, colourless
Z = 4	0.36 × 0.21 × 0.09 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3978 independent reflections
Radiation source: fine-focus sealed tube	2968 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.1°, θ_min = 2.2°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −44→45
T_min = 0.505, T_max = 0.827	l = −10→8
11039 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) = 0.103	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0492P)² + 0.6802P] where P = (F_o² + 2F_c²)/3
3978 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₂₂H₁₅BrClN₃O₃	V = 2019.4 (4) Å³
M_r = 484.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.2613 (7) Å	µ = 2.20 mm⁻¹
b = 36.688 (4) Å	T = 293 K
c = 8.7919 (9) Å	0.36 × 0.21 × 0.09 mm
β = 90.878 (2)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3978 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2968 reflections with I > 2σ(I)
T_min = 0.505, T_max = 0.827	R_int = 0.025
11039 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.04	Δρ_max = 0.48 e Å⁻³
3978 reflections	Δρ_min = −0.44 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	0.29655 (6)	0.490655 (9)	0.67871 (4)	0.06861 (15)
Cl1	0.06423 (18)	0.75440 (3)	1.24666 (14)	0.0966 (4)
O2	0.0115 (3)	0.64041 (5)	1.3681 (2)	0.0511 (5)
N1	0.3152 (3)	0.59119 (6)	1.5238 (2)	0.0427 (5)
C3	0.1975 (5)	0.52390 (8)	0.8274 (3)	0.0463 (7)
C18	0.5177 (4)	0.61307 (7)	1.7051 (3)	0.0413 (6)
N2	0.5149 (4)	0.57773 (6)	1.5071 (3)	0.0518 (6)
O1	−0.2188 (3)	0.60500 (7)	1.1628 (2)	0.0696 (7)
C17	0.3102 (4)	0.61371 (7)	1.6470 (3)	0.0380 (6)
C5	−0.0818 (5)	0.55733 (8)	0.9389 (3)	0.0501 (7)
H5A	−0.2247	0.5642	0.9399	0.060*
C6	0.0564 (4)	0.57085 (7)	1.0497 (3)	0.0406 (6)
C21	0.2051 (5)	0.65309 (8)	1.8413 (3)	0.0524 (7)
H21A	0.1020	0.6669	1.8898	0.063*
C10	−0.0114 (5)	0.67132 (8)	1.2854 (3)	0.0567 (8)
C9	0.1469 (5)	0.58149 (7)	1.4157 (3)	0.0458 (7)
H9A	0.0144	0.5782	1.4698	0.055*
H9B	0.1823	0.5585	1.3681	0.055*
O3	0.0745 (5)	0.67563 (7)	1.1669 (3)	0.0951 (9)
N3	0.6384 (4)	0.59032 (7)	1.6152 (3)	0.0523 (6)
C20	0.4137 (5)	0.65259 (8)	1.9019 (3)	0.0524 (7)
H20A	0.4446	0.6659	1.9895	0.063*
C19	0.5718 (5)	0.63304 (8)	1.8356 (3)	0.0510 (7)
H19A	0.7102	0.6330	1.8755	0.061*
C22	0.1482 (5)	0.63403 (8)	1.7136 (3)	0.0486 (7)
H22A	0.0099	0.6346	1.6736	0.058*
C2	0.3391 (5)	0.53722 (8)	0.9333 (4)	0.0550 (8)
H2B	0.4818	0.5303	0.9306	0.066*
C8	0.1142 (5)	0.61048 (7)	1.2923 (3)	0.0472 (7)
H8A	0.2516	0.6181	1.2510	0.057*
C1	0.2703 (4)	0.56101 (8)	1.0444 (3)	0.0491 (7)
H1A	0.3671	0.5704	1.1154	0.059*
C4	−0.0131 (5)	0.53398 (8)	0.8277 (3)	0.0527 (8)
H4A	−0.1079	0.5252	0.7540	0.063*
C7	−0.0336 (5)	0.59603 (8)	1.1656 (3)	0.0472 (7)
C16	−0.3280 (6)	0.68352 (9)	1.4437 (4)	0.0716 (10)
H16A	−0.3416	0.6585	1.4564	0.086*
C11	−0.1591 (5)	0.69699 (8)	1.3596 (3)	0.0524 (7)
C13	−0.2875 (6)	0.75732 (9)	1.4121 (5)	0.0779 (11)
H13A	−0.2728	0.7824	1.4022	0.093*
C14	−0.4524 (6)	0.74321 (10)	1.4933 (5)	0.0866 (12)
H14A	−0.5498	0.7588	1.5385	0.104*
C15	−0.4754 (7)	0.70624 (11)	1.5085 (5)	0.0896 (13)
H15A	−0.5894	0.6967	1.5621	0.108*
C12	−0.1430 (5)	0.73429 (8)	1.3451 (4)	0.0599 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0825 (3)	0.0610 (2)	0.0628 (2)	−0.00151 (17)	0.01525 (18)	−0.02185 (16)
Cl1	0.0949 (7)	0.0628 (6)	0.1336 (10)	−0.0065 (5)	0.0472 (7)	0.0038 (6)
O2	0.0750 (14)	0.0417 (11)	0.0368 (10)	0.0131 (9)	0.0022 (9)	−0.0028 (8)
N1	0.0460 (13)	0.0434 (12)	0.0384 (12)	0.0057 (10)	−0.0040 (10)	−0.0041 (10)
C3	0.0568 (19)	0.0380 (14)	0.0443 (16)	−0.0017 (13)	0.0071 (13)	−0.0027 (12)
C18	0.0418 (15)	0.0445 (15)	0.0375 (14)	0.0020 (12)	0.0005 (12)	0.0035 (11)
N2	0.0537 (15)	0.0513 (14)	0.0504 (14)	0.0146 (12)	0.0004 (12)	−0.0073 (11)
O1	0.0595 (15)	0.0880 (17)	0.0607 (14)	0.0290 (12)	−0.0135 (11)	−0.0193 (12)
C17	0.0459 (16)	0.0347 (13)	0.0336 (14)	0.0002 (11)	0.0031 (12)	−0.0001 (10)
C5	0.0438 (16)	0.0487 (17)	0.0574 (18)	0.0037 (13)	−0.0082 (14)	−0.0054 (14)
C6	0.0464 (16)	0.0359 (14)	0.0394 (14)	0.0038 (12)	−0.0018 (12)	−0.0002 (11)
C21	0.062 (2)	0.0535 (18)	0.0426 (16)	0.0045 (14)	0.0141 (14)	−0.0042 (13)
C10	0.086 (2)	0.0446 (16)	0.0396 (16)	0.0095 (16)	0.0076 (16)	−0.0013 (13)
C9	0.0574 (18)	0.0387 (14)	0.0412 (15)	0.0020 (13)	−0.0079 (13)	−0.0049 (11)
O3	0.161 (3)	0.0665 (16)	0.0589 (15)	0.0383 (16)	0.0511 (16)	0.0135 (12)
N3	0.0454 (14)	0.0581 (15)	0.0532 (15)	0.0105 (12)	−0.0046 (11)	−0.0044 (12)
C20	0.072 (2)	0.0463 (16)	0.0393 (16)	−0.0122 (15)	0.0065 (15)	−0.0061 (12)
C19	0.0537 (18)	0.0570 (18)	0.0422 (16)	−0.0130 (14)	−0.0054 (13)	0.0040 (13)
C22	0.0472 (17)	0.0555 (17)	0.0433 (16)	0.0024 (13)	0.0056 (13)	0.0001 (13)
C2	0.0432 (17)	0.0538 (18)	0.068 (2)	−0.0020 (14)	0.0022 (15)	−0.0118 (15)
C8	0.0598 (18)	0.0418 (15)	0.0401 (15)	0.0076 (13)	−0.0021 (13)	−0.0074 (12)
C1	0.0457 (17)	0.0488 (16)	0.0525 (17)	−0.0018 (13)	−0.0093 (13)	−0.0105 (13)
C4	0.062 (2)	0.0463 (16)	0.0499 (17)	−0.0020 (14)	−0.0124 (15)	−0.0095 (13)
C7	0.0543 (18)	0.0456 (16)	0.0416 (15)	0.0088 (14)	−0.0065 (13)	−0.0008 (12)
C16	0.094 (3)	0.0490 (18)	0.072 (2)	0.0104 (18)	0.027 (2)	0.0108 (16)
C11	0.071 (2)	0.0450 (16)	0.0411 (15)	0.0102 (15)	0.0085 (14)	0.0023 (12)
C13	0.091 (3)	0.0453 (19)	0.098 (3)	0.0152 (18)	0.025 (2)	0.0025 (18)
C14	0.095 (3)	0.064 (2)	0.102 (3)	0.026 (2)	0.039 (2)	0.004 (2)
C15	0.093 (3)	0.073 (3)	0.104 (3)	0.014 (2)	0.047 (2)	0.019 (2)
C12	0.069 (2)	0.0479 (17)	0.063 (2)	0.0050 (15)	0.0135 (16)	0.0039 (14)

Geometric parameters (Å, º) top

Br1—C3	1.899 (3)	C10—C11	1.479 (4)
Cl1—C12	1.736 (3)	C9—C8	1.531 (4)
O2—C10	1.353 (3)	C9—H9A	0.9700
O2—C8	1.441 (3)	C9—H9B	0.9700
N1—N2	1.355 (3)	C20—C19	1.361 (4)
N1—C17	1.363 (3)	C20—H20A	0.9300
N1—C9	1.452 (3)	C19—H19A	0.9300
C3—C2	1.366 (4)	C22—H22A	0.9300
C3—C4	1.369 (4)	C2—C1	1.384 (4)
C18—N3	1.382 (3)	C2—H2B	0.9300
C18—C17	1.388 (4)	C8—C7	1.532 (4)
C18—C19	1.399 (4)	C8—H8A	0.9800
N2—N3	1.301 (3)	C1—H1A	0.9300
O1—C7	1.205 (3)	C4—H4A	0.9300
C17—C22	1.395 (4)	C16—C15	1.374 (5)
C5—C4	1.374 (4)	C16—C11	1.390 (4)
C5—C6	1.385 (4)	C16—H16A	0.9300
C5—H5A	0.9300	C11—C12	1.378 (4)
C6—C1	1.388 (4)	C13—C14	1.366 (5)
C6—C7	1.492 (4)	C13—C12	1.377 (5)
C21—C22	1.365 (4)	C13—H13A	0.9300
C21—C20	1.403 (4)	C14—C15	1.371 (5)
C21—H21A	0.9300	C14—H14A	0.9300
C10—O3	1.191 (3)	C15—H15A	0.9300

C10—O2—C8	115.7 (2)	C21—C22—C17	115.9 (3)
N2—N1—C17	109.9 (2)	C21—C22—H22A	122.1
N2—N1—C9	120.1 (2)	C17—C22—H22A	122.1
C17—N1—C9	130.0 (2)	C3—C2—C1	120.1 (3)
C2—C3—C4	121.1 (3)	C3—C2—H2B	120.0
C2—C3—Br1	118.9 (2)	C1—C2—H2B	120.0
C4—C3—Br1	120.0 (2)	O2—C8—C9	104.9 (2)
N3—C18—C17	108.5 (2)	O2—C8—C7	109.3 (2)
N3—C18—C19	131.1 (3)	C9—C8—C7	110.4 (2)
C17—C18—C19	120.4 (3)	O2—C8—H8A	110.7
N3—N2—N1	109.3 (2)	C9—C8—H8A	110.7
N1—C17—C18	104.4 (2)	C7—C8—H8A	110.7
N1—C17—C22	133.1 (2)	C2—C1—C6	119.9 (3)
C18—C17—C22	122.5 (2)	C2—C1—H1A	120.0
C4—C5—C6	121.7 (3)	C6—C1—H1A	120.0
C4—C5—H5A	119.2	C3—C4—C5	118.8 (3)
C6—C5—H5A	119.2	C3—C4—H4A	120.6
C5—C6—C1	118.4 (2)	C5—C4—H4A	120.6
C5—C6—C7	117.6 (2)	O1—C7—C6	121.9 (3)
C1—C6—C7	124.0 (2)	O1—C7—C8	119.4 (3)
C22—C21—C20	122.4 (3)	C6—C7—C8	118.7 (2)
C22—C21—H21A	118.8	C15—C16—C11	121.8 (3)
C20—C21—H21A	118.8	C15—C16—H16A	119.1
O3—C10—O2	122.4 (3)	C11—C16—H16A	119.1
O3—C10—C11	126.5 (3)	C12—C11—C16	117.3 (3)
O2—C10—C11	111.0 (2)	C12—C11—C10	123.0 (3)
N1—C9—C8	112.4 (2)	C16—C11—C10	119.6 (3)
N1—C9—H9A	109.1	C14—C13—C12	119.9 (3)
C8—C9—H9A	109.1	C14—C13—H13A	120.1
N1—C9—H9B	109.1	C12—C13—H13A	120.1
C8—C9—H9B	109.1	C13—C14—C15	120.5 (3)
H9A—C9—H9B	107.9	C13—C14—H14A	119.8
N2—N3—C18	108.0 (2)	C15—C14—H14A	119.8
C19—C20—C21	121.5 (3)	C14—C15—C16	119.2 (4)
C19—C20—H20A	119.2	C14—C15—H15A	120.4
C21—C20—H20A	119.2	C16—C15—H15A	120.4
C20—C19—C18	117.3 (3)	C13—C12—C11	121.4 (3)
C20—C19—H19A	121.3	C13—C12—Cl1	117.0 (3)
C18—C19—H19A	121.3	C11—C12—Cl1	121.6 (2)

C17—N1—N2—N3	0.7 (3)	N1—C9—C8—C7	169.5 (2)
C9—N1—N2—N3	179.3 (2)	C3—C2—C1—C6	1.1 (5)
N2—N1—C17—C18	−0.3 (3)	C5—C6—C1—C2	−2.2 (4)
C9—N1—C17—C18	−178.8 (2)	C7—C6—C1—C2	179.5 (3)
N2—N1—C17—C22	−179.7 (3)	C2—C3—C4—C5	−1.3 (5)
C9—N1—C17—C22	1.8 (5)	Br1—C3—C4—C5	178.3 (2)
N3—C18—C17—N1	−0.1 (3)	C6—C5—C4—C3	0.1 (4)
C19—C18—C17—N1	−179.0 (2)	C5—C6—C7—O1	−1.2 (4)
N3—C18—C17—C22	179.4 (3)	C1—C6—C7—O1	177.1 (3)
C19—C18—C17—C22	0.4 (4)	C5—C6—C7—C8	178.2 (3)
C4—C5—C6—C1	1.6 (4)	C1—C6—C7—C8	−3.5 (4)
C4—C5—C6—C7	−180.0 (3)	O2—C8—C7—O1	−14.2 (4)
C8—O2—C10—O3	−10.7 (5)	C9—C8—C7—O1	100.7 (3)
C8—O2—C10—C11	167.3 (2)	O2—C8—C7—C6	166.4 (2)
N2—N1—C9—C8	−97.1 (3)	C9—C8—C7—C6	−78.7 (3)
C17—N1—C9—C8	81.3 (3)	C15—C16—C11—C12	0.8 (5)
N1—N2—N3—C18	−0.7 (3)	C15—C16—C11—C10	−176.8 (4)
C17—C18—N3—N2	0.5 (3)	O3—C10—C11—C12	−32.0 (6)
C19—C18—N3—N2	179.3 (3)	O2—C10—C11—C12	150.1 (3)
C22—C21—C20—C19	0.3 (5)	O3—C10—C11—C16	145.5 (4)
C21—C20—C19—C18	−0.7 (4)	O2—C10—C11—C16	−32.4 (4)
N3—C18—C19—C20	−178.4 (3)	C12—C13—C14—C15	0.0 (7)
C17—C18—C19—C20	0.3 (4)	C13—C14—C15—C16	1.3 (7)
C20—C21—C22—C17	0.4 (4)	C11—C16—C15—C14	−1.7 (6)
N1—C17—C22—C21	178.5 (3)	C14—C13—C12—C11	−0.9 (6)
C18—C17—C22—C21	−0.7 (4)	C14—C13—C12—Cl1	−179.0 (3)
C4—C3—C2—C1	0.7 (5)	C16—C11—C12—C13	0.5 (5)
Br1—C3—C2—C1	−178.9 (2)	C10—C11—C12—C13	178.0 (3)
C10—O2—C8—C9	172.5 (2)	C16—C11—C12—Cl1	178.5 (3)
C10—O2—C8—C7	−69.2 (3)	C10—C11—C12—Cl1	−3.9 (5)
N1—C9—C8—O2	−72.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···Cg1ⁱ	0.93	2.87	3.707	150
C21—H21A···O3ⁱⁱ	0.93	2.47	3.101 (4)	126

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₅BrClN₃O₃
M_r	484.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	6.2613 (7), 36.688 (4), 8.7919 (9)
β (°)	90.878 (2)
V (Å³)	2019.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.20
Crystal size (mm)	0.36 × 0.21 × 0.09

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.505, 0.827
No. of measured, independent and observed [I > 2σ(I)] reflections	11039, 3978, 2968
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.103, 1.04
No. of reflections	3978
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.44

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	2.872	3.707	150.22
C21—H21A···O3ⁱⁱ	0.93	2.466	3.101 (4)	125.71

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

Acknowledgements

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

References

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