2-(1H-1,2,3-Benzotriazol-1-yl)-1-m-toluoylethyl 2,4-dichloro­benzoate

Zeng, W.-L.

doi:10.1107/S1600536808011963

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o941

doi:10.1107/S1600536808011963

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2-(1H-1,2,3-Benzotriazol-1-yl)-1-m-toluoylethyl 2,4-dichlorobenzoate

Wu-Lan Zeng ^a ^*

^aMicroScale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: wulanzeng@163.com

(Received 13 April 2008; accepted 25 April 2008; online 30 April 2008)

In the title compound, C₂₃H₁₇Cl₂N₃O₃, the dihedral angles between the mean planes of the benzotriazole system and the methyl- and dichloro-substituted benzene rings are 47.72 (1) and 13.06 (1)°, respectively. In the crystal structure, intermolecular C—H⋯O and C—H⋯π interactions help to consolidate the packing.

Related literature

For background, see Chen & Wu (2005 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₃H₁₇Cl₂N₃O₃
M_r = 454.30
Monoclinic, P 2₁ /c
a = 9.3395 (19) Å
b = 9.3065 (19) Å
c = 23.538 (5) Å
β = 92.10 (3)°
V = 2044.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 113 (2) K
0.18 × 0.16 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.940, T_max = 0.973
11260 measured reflections
3585 independent reflections
3138 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.091
S = 1.10
3585 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1ⁱ	0.93	2.35	3.263 (2)	168
C4—H4⋯Cg1ⁱⁱ	0.93	2.86	3.4645 (19)	124
Symmetry codes: (i) -x+1, -y+2, -z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C18–C23 ring.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011963/hb2721sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011963/hb2721Isup2.hkl

checkCIF report

Comment top

1H-Benzotriazole and its derivatives exhibit a broad spectrum of pharmacological activities such as antifungal, antitumor and antineoplastic activities (Chen & Wu, 2005). We report here the synthesis and structure of the title compound, (I) (Fig. 1), as part of our ongoing studies on new benzotriazole compounds with higher bioactivity.

The molecule of (I) is chiral. In the arbitrarily chosen asymmetric molecule, C9 has S configuration, but crystal symmetry generates a racemic mixture. Otherwise, all the bond lengths and angles in (I) are within their normal ranges (Allen et al., 1987). The benzotriazole ring system is essentially planar, with a dihedral angle of 2.2 (8)° between the triazole ring (atoms N1—N3/C18/C23) and the C18—C23 benzene ring. The dihedral angles between the mean planes of the benzotriazole system and the C1—C6 and C11—C15 aromatic rings are 47.72 (1)° and 13.06 (1)°, respectively. The dihedral angle between rings C1—C6 and C11—C15 is 35.26 (2)°.

In the crystal, intermolecular C-H···O and C-H···π interactions (Table 1) help to consolidate the packing.

Related literature top

For background, see Chen & Wu (2005). For reference structural data, see: Allen et al. (1987).

Experimental top

Bromine (3.2 g, 0.02 mol) was added dropwise to a solution of 3-(1H-benzo[d][1,2,3]triazol-1-yl)-1-m-tolylpropan-1-one (5.30 g, 0.02 mol) and sodium acetate (1.6 g, 0.02 mol) in acetic acid (50 ml). The reaction proceeded for 7 h. Water (50 ml) and chloroform (20 ml) were then added. The organic layer was washed successively with saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and the chloroform solution filtered. It was cooled with ice-water, and then an acetone solution (10 ml) of 2-chlorobenzoic acid (3.8 g, 0.02 mol) and triethylamine (2.8 ml) was added. The mixture was stirred with ice-water for 6 h. The solution was then filtered and concentrated. Colourless slabs of (I) were obtained by slow evaporation of ethanol solution at room temperature after one week.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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).

Figures top

Fig. 1. The molecular structure of (I), drawn with 50% probability ellipsoids (arbitrary spheres for the H atoms).

2-(1H-1,2,3-Benzotriazol-1-yl)-1-m-toluoylethyl 2,4-dichlorobenzoate top

Crystal data top

C₂₃H₁₇Cl₂N₃O₃	F(000) = 936
M_r = 454.30	D_x = 1.476 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5663 reflections
a = 9.3395 (19) Å	θ = 1.7–27.9°
b = 9.3065 (19) Å	µ = 0.35 mm⁻¹
c = 23.538 (5) Å	T = 113 K
β = 92.10 (3)°	Slab, colourless
V = 2044.5 (7) Å³	0.18 × 0.16 × 0.08 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3585 independent reflections
Radiation source: X-ray tube	3138 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→10
T_min = 0.940, T_max = 0.973	k = −11→10
11260 measured reflections	l = −27→20

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0569P)² + 0.0675P] where P = (F_o² + 2F_c²)/3
3585 reflections	(Δ/σ)_max = 0.001
281 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₃H₁₇Cl₂N₃O₃	V = 2044.5 (7) Å³
M_r = 454.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.3395 (19) Å	µ = 0.35 mm⁻¹
b = 9.3065 (19) Å	T = 113 K
c = 23.538 (5) Å	0.18 × 0.16 × 0.08 mm
β = 92.10 (3)°

Data collection top

Bruker SMART CCD diffractometer	3585 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	3138 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.973	R_int = 0.031
11260 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.10	Δρ_max = 0.24 e Å⁻³
3585 reflections	Δρ_min = −0.30 e Å⁻³
281 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
Cl1	0.16956 (4)	0.45085 (4)	0.044626 (17)	0.02736 (13)
Cl2	0.48958 (4)	0.53198 (5)	−0.135572 (17)	0.03077 (14)
O1	0.28238 (12)	1.07298 (12)	0.10792 (5)	0.0272 (3)
O2	0.37879 (10)	0.80863 (11)	0.11568 (4)	0.0208 (3)
O3	0.14534 (11)	0.76130 (12)	0.09646 (5)	0.0309 (3)
N1	0.58217 (13)	0.98801 (13)	0.18828 (6)	0.0199 (3)
N2	0.61195 (13)	1.10055 (14)	0.22405 (6)	0.0255 (3)
N3	0.71818 (13)	1.17383 (14)	0.20467 (6)	0.0279 (3)
C1	0.22159 (14)	1.10721 (16)	0.20360 (7)	0.0189 (3)
C2	0.18316 (15)	1.04219 (16)	0.25408 (7)	0.0194 (3)
H2	0.1983	0.9441	0.2590	0.023*
C3	0.12259 (14)	1.12125 (16)	0.29721 (7)	0.0209 (3)
C4	0.10223 (15)	1.26887 (16)	0.28894 (7)	0.0228 (4)
H4	0.0603	1.3232	0.3170	0.027*
C5	0.14371 (15)	1.33491 (17)	0.23954 (7)	0.0244 (4)
H5	0.1320	1.4336	0.2352	0.029*
C6	0.20216 (15)	1.25563 (16)	0.19677 (7)	0.0231 (4)
H6	0.2287	1.3004	0.1634	0.028*
C7	0.08028 (17)	1.05045 (18)	0.35132 (7)	0.0272 (4)
H7A	−0.0178	1.0198	0.3476	0.041*
H7B	0.0908	1.1176	0.3822	0.041*
H7C	0.1407	0.9687	0.3588	0.041*
C8	0.27983 (15)	1.02509 (16)	0.15583 (7)	0.0197 (3)
C9	0.34219 (15)	0.87504 (16)	0.16804 (6)	0.0198 (3)
H9	0.2707	0.8162	0.1867	0.024*
C10	0.26778 (15)	0.75666 (16)	0.08292 (7)	0.0213 (3)
C11	0.32137 (15)	0.69822 (16)	0.02907 (7)	0.0194 (3)
C12	0.28115 (15)	0.56368 (16)	0.00791 (7)	0.0193 (3)
C13	0.33423 (15)	0.51230 (17)	−0.04221 (6)	0.0212 (4)
H13	0.3086	0.4214	−0.0555	0.025*
C14	0.42553 (15)	0.59738 (17)	−0.07222 (7)	0.0221 (3)
C15	0.46799 (15)	0.73162 (17)	−0.05280 (7)	0.0239 (4)
H15	0.5301	0.7878	−0.0734	0.029*
C16	0.41582 (15)	0.77997 (17)	−0.00211 (7)	0.0220 (3)
H16	0.4445	0.8696	0.0116	0.026*
C17	0.47953 (15)	0.87985 (16)	0.20522 (7)	0.0210 (3)
H17A	0.4545	0.8983	0.2442	0.025*
H17B	0.5251	0.7863	0.2043	0.025*
C18	0.67506 (14)	0.98839 (16)	0.14484 (7)	0.0188 (3)
C19	0.69518 (16)	0.89704 (17)	0.09888 (7)	0.0227 (4)
H19	0.6366	0.8177	0.0919	0.027*
C20	0.80604 (16)	0.93045 (19)	0.06451 (8)	0.0300 (4)
H20	0.8227	0.8727	0.0332	0.036*
C21	0.89552 (17)	1.05053 (19)	0.07554 (8)	0.0342 (4)
H21	0.9701	1.0692	0.0515	0.041*
C22	0.87541 (16)	1.13949 (18)	0.12039 (8)	0.0301 (4)
H22	0.9346	1.2184	0.1273	0.036*
C23	0.76221 (15)	1.10800 (16)	0.15590 (7)	0.0239 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0300 (2)	0.0263 (2)	0.0262 (2)	−0.00985 (15)	0.00706 (17)	−0.00106 (17)
Cl2	0.0362 (2)	0.0404 (3)	0.0161 (2)	0.00522 (17)	0.00562 (18)	−0.00085 (17)
O1	0.0329 (6)	0.0272 (6)	0.0216 (7)	−0.0044 (5)	0.0046 (5)	0.0035 (5)
O2	0.0188 (5)	0.0247 (6)	0.0192 (6)	−0.0027 (4)	0.0041 (4)	−0.0069 (5)
O3	0.0210 (6)	0.0373 (7)	0.0351 (8)	−0.0070 (5)	0.0090 (5)	−0.0115 (6)
N1	0.0210 (6)	0.0172 (6)	0.0214 (8)	0.0009 (5)	0.0001 (5)	−0.0044 (5)
N2	0.0260 (7)	0.0209 (7)	0.0294 (8)	0.0027 (5)	−0.0027 (6)	−0.0096 (6)
N3	0.0238 (7)	0.0219 (7)	0.0378 (9)	−0.0003 (5)	−0.0015 (6)	−0.0053 (7)
C1	0.0153 (7)	0.0201 (8)	0.0212 (9)	−0.0003 (6)	−0.0013 (6)	−0.0009 (7)
C2	0.0160 (7)	0.0183 (8)	0.0241 (9)	0.0002 (5)	0.0013 (6)	−0.0017 (7)
C3	0.0144 (7)	0.0257 (8)	0.0224 (9)	0.0005 (6)	−0.0013 (6)	−0.0035 (7)
C4	0.0166 (7)	0.0245 (8)	0.0271 (9)	0.0026 (6)	−0.0012 (6)	−0.0086 (7)
C5	0.0225 (8)	0.0176 (8)	0.0326 (10)	0.0027 (6)	−0.0056 (7)	−0.0015 (7)
C6	0.0209 (8)	0.0227 (8)	0.0253 (9)	−0.0012 (6)	−0.0028 (7)	0.0036 (7)
C7	0.0264 (8)	0.0320 (9)	0.0234 (9)	−0.0006 (7)	0.0050 (7)	−0.0050 (7)
C8	0.0166 (7)	0.0215 (8)	0.0210 (9)	−0.0056 (6)	0.0023 (6)	0.0008 (7)
C9	0.0225 (8)	0.0196 (8)	0.0176 (8)	−0.0022 (6)	0.0072 (6)	−0.0030 (6)
C10	0.0211 (8)	0.0195 (8)	0.0235 (9)	−0.0036 (6)	0.0029 (7)	−0.0005 (7)
C11	0.0174 (7)	0.0218 (8)	0.0188 (9)	0.0011 (6)	−0.0008 (6)	−0.0005 (7)
C12	0.0172 (7)	0.0213 (8)	0.0194 (8)	−0.0012 (6)	−0.0006 (6)	0.0026 (6)
C13	0.0239 (8)	0.0206 (8)	0.0189 (9)	0.0014 (6)	−0.0025 (7)	−0.0015 (7)
C14	0.0231 (8)	0.0293 (9)	0.0140 (8)	0.0059 (6)	0.0010 (6)	0.0024 (7)
C15	0.0231 (8)	0.0275 (9)	0.0211 (9)	−0.0013 (6)	0.0020 (7)	0.0063 (7)
C16	0.0228 (8)	0.0214 (8)	0.0217 (9)	−0.0023 (6)	0.0005 (7)	0.0014 (7)
C17	0.0242 (8)	0.0204 (8)	0.0185 (9)	0.0015 (6)	0.0038 (6)	−0.0006 (7)
C18	0.0164 (7)	0.0171 (7)	0.0230 (9)	0.0025 (6)	−0.0006 (6)	0.0016 (6)
C19	0.0208 (7)	0.0224 (8)	0.0249 (9)	−0.0005 (6)	0.0003 (7)	−0.0030 (7)
C20	0.0250 (8)	0.0346 (10)	0.0305 (10)	0.0012 (7)	0.0047 (7)	−0.0046 (8)
C21	0.0231 (9)	0.0382 (10)	0.0418 (12)	−0.0030 (7)	0.0100 (8)	0.0046 (9)
C22	0.0224 (8)	0.0237 (9)	0.0442 (12)	−0.0049 (6)	−0.0004 (8)	0.0019 (8)
C23	0.0209 (8)	0.0173 (8)	0.0332 (10)	0.0016 (6)	−0.0039 (7)	−0.0020 (7)

Geometric parameters (Å, º) top

Cl1—C12	1.7326 (15)	C8—C9	1.536 (2)
Cl2—C14	1.7370 (16)	C9—C17	1.527 (2)
O1—C8	1.2136 (19)	C9—H9	0.9800
O2—C10	1.3582 (18)	C10—C11	1.483 (2)
O2—C9	1.4313 (18)	C11—C16	1.394 (2)
O3—C10	1.1990 (18)	C11—C12	1.394 (2)
N1—C18	1.365 (2)	C12—C13	1.382 (2)
N1—N2	1.3660 (18)	C13—C14	1.377 (2)
N1—C17	1.4557 (19)	C13—H13	0.9300
N2—N3	1.3004 (19)	C14—C15	1.383 (2)
N3—C23	1.377 (2)	C15—C16	1.381 (2)
C1—C2	1.392 (2)	C15—H15	0.9300
C1—C6	1.402 (2)	C16—H16	0.9300
C1—C8	1.480 (2)	C17—H17A	0.9700
C2—C3	1.391 (2)	C17—H17B	0.9700
C2—H2	0.9300	C18—C19	1.394 (2)
C3—C4	1.400 (2)	C18—C23	1.398 (2)
C3—C7	1.500 (2)	C19—C20	1.373 (2)
C4—C5	1.383 (2)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.414 (2)
C5—C6	1.377 (2)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.360 (3)
C6—H6	0.9300	C21—H21	0.9300
C7—H7A	0.9600	C22—C23	1.403 (2)
C7—H7B	0.9600	C22—H22	0.9300
C7—H7C	0.9600

C10—O2—C9	116.18 (11)	C16—C11—C12	118.02 (15)
C18—N1—N2	109.82 (12)	C16—C11—C10	119.32 (14)
C18—N1—C17	130.54 (13)	C12—C11—C10	122.67 (14)
N2—N1—C17	118.85 (13)	C13—C12—C11	121.03 (14)
N3—N2—N1	109.06 (13)	C13—C12—Cl1	117.22 (12)
N2—N3—C23	108.31 (13)	C11—C12—Cl1	121.69 (12)
C2—C1—C6	119.34 (14)	C14—C13—C12	119.16 (15)
C2—C1—C8	122.52 (14)	C14—C13—H13	120.4
C6—C1—C8	118.13 (14)	C12—C13—H13	120.4
C3—C2—C1	121.17 (14)	C13—C14—C15	121.67 (15)
C3—C2—H2	119.4	C13—C14—Cl2	118.56 (13)
C1—C2—H2	119.4	C15—C14—Cl2	119.77 (12)
C2—C3—C4	118.33 (15)	C16—C15—C14	118.29 (14)
C2—C3—C7	120.96 (14)	C16—C15—H15	120.9
C4—C3—C7	120.72 (14)	C14—C15—H15	120.9
C5—C4—C3	120.83 (15)	C15—C16—C11	121.81 (15)
C5—C4—H4	119.6	C15—C16—H16	119.1
C3—C4—H4	119.6	C11—C16—H16	119.1
C6—C5—C4	120.49 (15)	N1—C17—C9	114.27 (12)
C6—C5—H5	119.8	N1—C17—H17A	108.7
C4—C5—H5	119.8	C9—C17—H17A	108.7
C5—C6—C1	119.82 (15)	N1—C17—H17B	108.7
C5—C6—H6	120.1	C9—C17—H17B	108.7
C1—C6—H6	120.1	H17A—C17—H17B	107.6
C3—C7—H7A	109.5	N1—C18—C19	133.41 (14)
C3—C7—H7B	109.5	N1—C18—C23	104.14 (14)
H7A—C7—H7B	109.5	C19—C18—C23	122.41 (15)
C3—C7—H7C	109.5	C20—C19—C18	116.44 (15)
H7A—C7—H7C	109.5	C20—C19—H19	121.8
H7B—C7—H7C	109.5	C18—C19—H19	121.8
O1—C8—C1	122.46 (14)	C19—C20—C21	121.62 (17)
O1—C8—C9	119.18 (14)	C19—C20—H20	119.2
C1—C8—C9	118.34 (13)	C21—C20—H20	119.2
O2—C9—C17	106.50 (11)	C22—C21—C20	121.75 (16)
O2—C9—C8	109.41 (12)	C22—C21—H21	119.1
C17—C9—C8	112.67 (12)	C20—C21—H21	119.1
O2—C9—H9	109.4	C21—C22—C23	117.64 (15)
C17—C9—H9	109.4	C21—C22—H22	121.2
C8—C9—H9	109.4	C23—C22—H22	121.2
O3—C10—O2	123.50 (15)	N3—C23—C18	108.66 (14)
O3—C10—C11	126.53 (14)	N3—C23—C22	131.17 (14)
O2—C10—C11	109.96 (12)	C18—C23—C22	120.13 (15)

C18—N1—N2—N3	1.08 (16)	C10—C11—C12—Cl1	−2.4 (2)
C17—N1—N2—N3	171.98 (12)	C11—C12—C13—C14	−1.6 (2)
N1—N2—N3—C23	−1.23 (16)	Cl1—C12—C13—C14	−178.78 (11)
C6—C1—C2—C3	1.6 (2)	C12—C13—C14—C15	1.5 (2)
C8—C1—C2—C3	−177.02 (13)	C12—C13—C14—Cl2	−179.24 (11)
C1—C2—C3—C4	−0.6 (2)	C13—C14—C15—C16	−0.3 (2)
C1—C2—C3—C7	179.50 (13)	Cl2—C14—C15—C16	−179.58 (11)
C2—C3—C4—C5	−1.2 (2)	C14—C15—C16—C11	−0.8 (2)
C7—C3—C4—C5	178.73 (13)	C12—C11—C16—C15	0.7 (2)
C3—C4—C5—C6	1.9 (2)	C10—C11—C16—C15	−179.33 (13)
C4—C5—C6—C1	−0.9 (2)	C18—N1—C17—C9	−77.26 (19)
C2—C1—C6—C5	−0.9 (2)	N2—N1—C17—C9	114.04 (14)
C8—C1—C6—C5	177.82 (13)	O2—C9—C17—N1	74.44 (15)
C2—C1—C8—O1	162.53 (14)	C8—C9—C17—N1	−45.52 (17)
C6—C1—C8—O1	−16.1 (2)	N2—N1—C18—C19	177.33 (15)
C2—C1—C8—C9	−18.9 (2)	C17—N1—C18—C19	7.8 (3)
C6—C1—C8—C9	162.47 (13)	N2—N1—C18—C23	−0.46 (16)
C10—O2—C9—C17	162.00 (12)	C17—N1—C18—C23	−169.96 (14)
C10—O2—C9—C8	−75.96 (15)	N1—C18—C19—C20	−177.49 (16)
O1—C8—C9—O2	−7.23 (18)	C23—C18—C19—C20	0.0 (2)
C1—C8—C9—O2	174.12 (11)	C18—C19—C20—C21	0.5 (2)
O1—C8—C9—C17	111.04 (15)	C19—C20—C21—C22	−0.6 (3)
C1—C8—C9—C17	−67.61 (17)	C20—C21—C22—C23	0.2 (3)
C9—O2—C10—O3	−1.8 (2)	N2—N3—C23—C18	0.94 (17)
C9—O2—C10—C11	177.09 (12)	N2—N3—C23—C22	−176.75 (16)
O3—C10—C11—C16	130.70 (17)	N1—C18—C23—N3	−0.27 (17)
O2—C10—C11—C16	−48.10 (18)	C19—C18—C23—N3	−178.38 (13)
O3—C10—C11—C12	−49.3 (2)	N1—C18—C23—C22	177.72 (14)
O2—C10—C11—C12	131.91 (14)	C19—C18—C23—C22	−0.4 (2)
C16—C11—C12—C13	0.5 (2)	C21—C22—C23—N3	177.76 (16)
C10—C11—C12—C13	−179.47 (13)	C21—C22—C23—C18	0.3 (2)
C16—C11—C12—Cl1	177.60 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1ⁱ	0.93	2.35	3.263 (2)	168
C4—H4···Cg1ⁱⁱ	0.93	2.86	3.4645 (19)	124

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇Cl₂N₃O₃
M_r	454.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	9.3395 (19), 9.3065 (19), 23.538 (5)
β (°)	92.10 (3)
V (Å³)	2044.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.18 × 0.16 × 0.08

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.940, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	11260, 3585, 3138
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.091, 1.10
No. of reflections	3585
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.30

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1ⁱ	0.93	2.35	3.263 (2)	168
C4—H4···Cg1ⁱⁱ	0.93	2.86	3.4645 (19)	124

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, y+1/2, −z+1/2.

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. CrossRef Web of Science Google Scholar
Bruker (1997). SMART, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Z.-Y. & Wu, M.-J. (2005). Org. Lett. 7, 475–477. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 5| May 2008| Page o941

doi:10.1107/S1600536808011963

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