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

Jiang, L.-B.; Li, L.; Liu, Y.; Tian, N.-N.; Wan, J.

doi:10.1107/S1600536808023222

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1619

doi:10.1107/S1600536808023222

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

Lin-Bin Jiang,^a Lin Li,^a Yao Liu,^b Na-Na Tian ^b and Jun Wan ^b ^*

^aCollege of Chemistry and Chemical Engineering, Guangxi University, 530004 Nanning, Guangxi, People's Republic of China, and ^bCollege 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 16 July 2008; accepted 23 July 2008; online 31 July 2008)

In the molecule of the title compound, C₂₃H₁₈ClN₃O₃, the essentially planar benzotriazole ring makes dihedral angles of 52.93 (1) and 85.21 (1)°, respectively, with the chlorophenyl and tolyl rings. The crystal packing is stabilized by π–π [centroid-to-centroid distance 3.830 (2) Å, interplanar distance 3.705 Å, slippage 0.968 Å]; C—H⋯π⋯tolyl ring interactions are also present.

Related literature

For related literature, see: Bi et al., (2007 ); Allen et al. (1987 ).

Experimental

Crystal data

C₂₃H₁₈ClN₃O₃
M_r = 419.85
Monoclinic, P 2₁ /c
a = 7.9254 (7) Å
b = 26.151 (2) Å
c = 10.6002 (9) Å
β = 107.895 (1)°
V = 2090.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 (2) K
0.31 × 0.17 × 0.07 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.934, T_max = 0.983
11618 measured reflections
4112 independent reflections
2671 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.155
S = 1.02
4112 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
C—H⋯π interactions (Å, °)

Cg4 is the centroid of the tolyl ring.

	C—H	C⋯Cg	C—H⋯Cg	H⋯Cg
C2—H2B⋯Cg4ⁱⁱ	0.93	3.879 (3)	168	2.96
Symmetry codes: (i) 2-x, 2-y, 2-z; (ii) $[x-1, -y+{3 \over 2}, z-{1 \over 2}]$ .

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/S1600536808023222/dn2368sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023222/dn2368Isup2.hkl

checkCIF report

Comment top

Recently we have reported the structure of 2-(1H-benzotriazol-1-yl)-1-(2-fluorobenzoyl)ethyl benzoate (II) (Bi et al., 2007). As part of our ongoing studies on benzotriazole derivatives with higher pharmacological activities, the title compound (I) was synthesized and its structure is shown here.

In (I), all bond lengths and angles are within normal ranges (Allen et al., 1987) and are comparable with those in the related compound (II). In (I), the benzotriazole moiety is essentially planar with a dihedral angle of 0.46 (1)° between the N1–N3/C10/C11 triazole ring (A) and C10–C15 phenyl ring (B). The whole molecular is non-planar (Fig. 1). The benzotriazole system makes dihedral angles of 52.93 (1)° and 85.21 (1)° with the chlorophenyl C1–C6 (C) and the tolyl C17–C22 (D) rings respectively. The dihedral between the two phenyl rings, viz. C and D, is 34.40 (1)°.

The crystal packing is stabilized by slippest π–π and weak C—H···π interactions involving the tolyl ring D (Table 1).

Related literature top

For related literature, see: Bi et al., (2007); Allen et al. (1987).

Experimental top

The title compound was prepared according to the literature method of Bi 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 6 d.

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. Molecular structure of compound (I) with the atom-labelling scheme. Ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.

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

Crystal data top

C₂₃H₁₈ClN₃O₃	F(000) = 872
M_r = 419.85	D_x = 1.334 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2285 reflections
a = 7.9254 (7) Å	θ = 2.6–21.5°
b = 26.151 (2) Å	µ = 0.21 mm⁻¹
c = 10.6002 (9) Å	T = 293 K
β = 107.895 (1)°	Plate, colourless
V = 2090.7 (3) Å³	0.31 × 0.17 × 0.07 mm
Z = 4

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	4112 independent reflections
Radiation source: fine-focus sealed tube	2671 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.0°, θ_min = 2.2°
ω scans	h = −7→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −31→32
T_min = 0.934, T_max = 0.983	l = −13→11
11618 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0736P)² + 0.3577P] where P = (F_o² + 2F_c²)/3
4112 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₃H₁₈ClN₃O₃	V = 2090.7 (3) Å³
M_r = 419.85	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9254 (7) Å	µ = 0.21 mm⁻¹
b = 26.151 (2) Å	T = 293 K
c = 10.6002 (9) Å	0.31 × 0.17 × 0.07 mm
β = 107.895 (1)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	4112 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2671 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.983	R_int = 0.032
11618 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.02	Δρ_max = 0.35 e Å⁻³
4112 reflections	Δρ_min = −0.14 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
Cl1	0.45657 (13)	0.67700 (3)	0.76685 (8)	0.0850 (3)
O2	0.6915 (2)	0.85387 (6)	0.88074 (15)	0.0519 (4)
N1	0.5321 (3)	0.85694 (8)	0.61201 (19)	0.0494 (5)
C16	0.7125 (3)	0.88114 (9)	0.9930 (2)	0.0521 (6)
O1	0.6508 (2)	0.76281 (7)	0.9880 (2)	0.0724 (6)
C10	0.6819 (3)	0.87350 (9)	0.5879 (2)	0.0447 (6)
C6	0.3402 (3)	0.75625 (9)	0.8833 (2)	0.0483 (6)
O3	0.6005 (3)	0.88270 (8)	1.0475 (2)	0.0811 (6)
C11	0.6356 (3)	0.92094 (10)	0.5281 (2)	0.0518 (6)
N2	0.4019 (3)	0.89243 (9)	0.5702 (2)	0.0627 (6)
C17	0.8850 (3)	0.90815 (9)	1.0357 (2)	0.0501 (6)
N3	0.4614 (3)	0.93082 (9)	0.5193 (2)	0.0679 (6)
C8	0.5253 (3)	0.82806 (9)	0.8302 (2)	0.0479 (6)
H8A	0.4285	0.8511	0.8316	0.058*
C22	1.0019 (3)	0.90722 (10)	0.9622 (3)	0.0606 (7)
H22A	0.9731	0.8894	0.8825	0.073*
C15	0.8502 (3)	0.85257 (11)	0.6109 (3)	0.0576 (7)
H15A	0.8805	0.8207	0.6501	0.069*
C7	0.5192 (3)	0.78034 (9)	0.9101 (2)	0.0493 (6)
C9	0.5084 (3)	0.81338 (10)	0.6880 (2)	0.0537 (6)
H9A	0.5967	0.7877	0.6881	0.064*
H9B	0.3923	0.7986	0.6467	0.064*
C20	1.2093 (4)	0.95912 (10)	1.1248 (3)	0.0649 (8)
C5	0.2118 (4)	0.78141 (11)	0.9250 (3)	0.0644 (7)
H5A	0.2369	0.8132	0.9659	0.077*
C1	0.3004 (4)	0.70910 (10)	0.8229 (3)	0.0597 (7)
C14	0.9684 (4)	0.88207 (12)	0.5720 (3)	0.0689 (8)
H14A	1.0827	0.8698	0.5857	0.083*
C2	0.1361 (5)	0.68742 (13)	0.8019 (3)	0.0889 (11)
H2B	0.1093	0.6560	0.7591	0.107*
C18	0.9309 (4)	0.93510 (11)	1.1532 (3)	0.0678 (8)
H18A	0.8530	0.9365	1.2032	0.081*
C12	0.7585 (4)	0.94992 (11)	0.4889 (3)	0.0681 (8)
H12A	0.7290	0.9816	0.4483	0.082*
C13	0.9234 (4)	0.92969 (12)	0.5129 (3)	0.0703 (8)
H13A	1.0088	0.9483	0.4890	0.084*
C19	1.0918 (4)	0.95997 (11)	1.1968 (3)	0.0745 (9)
H19A	1.1214	0.9777	1.2766	0.089*
C21	1.1613 (4)	0.93279 (11)	1.0071 (3)	0.0698 (8)
H21A	1.2383	0.9322	0.9563	0.084*
C23	1.3858 (4)	0.98627 (13)	1.1738 (3)	0.0903 (11)
H23A	1.4513	0.9809	1.1124	0.135*
H23B	1.4519	0.9730	1.2591	0.135*
H23C	1.3663	1.0222	1.1812	0.135*
C4	0.0476 (4)	0.75943 (16)	0.9057 (4)	0.0883 (11)
H4B	−0.0379	0.7762	0.9338	0.106*
C3	0.0112 (5)	0.71282 (17)	0.8449 (4)	0.1012 (13)
H3B	−0.0994	0.6980	0.8325	0.121*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1093 (7)	0.0709 (5)	0.0759 (5)	0.0079 (4)	0.0300 (5)	−0.0074 (4)
O2	0.0451 (10)	0.0619 (11)	0.0536 (10)	−0.0130 (8)	0.0225 (8)	−0.0098 (8)
N1	0.0367 (11)	0.0624 (13)	0.0496 (11)	−0.0072 (10)	0.0142 (9)	0.0039 (10)
C16	0.0540 (16)	0.0540 (15)	0.0527 (15)	−0.0025 (12)	0.0228 (13)	−0.0039 (12)
O1	0.0438 (11)	0.0846 (14)	0.0856 (14)	0.0002 (10)	0.0152 (10)	0.0217 (11)
C10	0.0345 (13)	0.0591 (15)	0.0419 (12)	−0.0108 (11)	0.0137 (10)	−0.0052 (11)
C6	0.0427 (14)	0.0576 (15)	0.0465 (13)	−0.0047 (11)	0.0165 (11)	0.0085 (11)
O3	0.0696 (14)	0.1081 (16)	0.0804 (14)	−0.0179 (12)	0.0449 (12)	−0.0298 (12)
C11	0.0471 (16)	0.0581 (16)	0.0501 (14)	−0.0084 (12)	0.0149 (12)	−0.0014 (11)
N2	0.0390 (12)	0.0761 (16)	0.0724 (15)	−0.0028 (11)	0.0163 (11)	0.0049 (12)
C17	0.0545 (16)	0.0477 (13)	0.0482 (14)	−0.0009 (11)	0.0158 (12)	−0.0027 (11)
N3	0.0504 (15)	0.0699 (15)	0.0814 (16)	0.0030 (11)	0.0174 (12)	0.0120 (12)
C8	0.0378 (13)	0.0547 (15)	0.0548 (14)	−0.0090 (11)	0.0194 (11)	−0.0034 (11)
C22	0.0516 (16)	0.0700 (17)	0.0598 (16)	−0.0093 (13)	0.0164 (13)	−0.0141 (13)
C15	0.0457 (16)	0.0662 (17)	0.0640 (16)	−0.0009 (12)	0.0215 (13)	−0.0002 (13)
C7	0.0443 (15)	0.0570 (15)	0.0518 (14)	−0.0008 (12)	0.0225 (12)	−0.0018 (12)
C9	0.0494 (15)	0.0618 (16)	0.0532 (14)	−0.0150 (12)	0.0206 (12)	−0.0043 (12)
C20	0.0551 (17)	0.0583 (17)	0.0679 (18)	−0.0077 (13)	−0.0008 (14)	0.0008 (14)
C5	0.0508 (17)	0.0745 (18)	0.0741 (18)	0.0048 (14)	0.0283 (14)	0.0126 (15)
C1	0.0618 (18)	0.0566 (16)	0.0583 (16)	−0.0050 (13)	0.0150 (13)	0.0094 (13)
C14	0.0421 (15)	0.092 (2)	0.079 (2)	−0.0107 (15)	0.0283 (14)	−0.0150 (17)
C2	0.078 (3)	0.077 (2)	0.095 (2)	−0.0308 (19)	0.002 (2)	0.0156 (18)
C18	0.072 (2)	0.0725 (19)	0.0608 (17)	−0.0042 (15)	0.0226 (15)	−0.0104 (14)
C12	0.069 (2)	0.0677 (18)	0.0687 (18)	−0.0202 (15)	0.0221 (15)	0.0041 (14)
C13	0.064 (2)	0.085 (2)	0.0726 (19)	−0.0302 (17)	0.0367 (16)	−0.0098 (16)
C19	0.079 (2)	0.075 (2)	0.0608 (18)	−0.0149 (16)	0.0086 (16)	−0.0176 (15)
C21	0.0545 (17)	0.080 (2)	0.077 (2)	−0.0132 (15)	0.0236 (15)	−0.0113 (16)
C23	0.065 (2)	0.090 (2)	0.099 (2)	−0.0200 (17)	−0.0015 (17)	−0.0090 (19)
C4	0.0479 (19)	0.112 (3)	0.112 (3)	0.0068 (19)	0.0347 (18)	0.038 (2)
C3	0.048 (2)	0.116 (3)	0.130 (3)	−0.026 (2)	0.015 (2)	0.047 (3)

Geometric parameters (Å, º) top

Cl1—C1	1.744 (3)	C9—H9A	0.9700
O2—C16	1.353 (3)	C9—H9B	0.9700
O2—C8	1.429 (3)	C20—C21	1.372 (4)
N1—N2	1.357 (3)	C20—C19	1.374 (4)
N1—C10	1.360 (3)	C20—C23	1.512 (4)
N1—C9	1.441 (3)	C5—C4	1.379 (4)
C16—O3	1.200 (3)	C5—H5A	0.9300
C16—C17	1.480 (3)	C1—C2	1.374 (4)
O1—C7	1.204 (3)	C14—C13	1.391 (4)
C10—C11	1.390 (3)	C14—H14A	0.9300
C10—C15	1.392 (3)	C2—C3	1.381 (5)
C6—C1	1.381 (4)	C2—H2B	0.9300
C6—C5	1.392 (4)	C18—C19	1.378 (4)
C6—C7	1.498 (3)	C18—H18A	0.9300
C11—N3	1.380 (3)	C12—C13	1.359 (4)
C11—C12	1.394 (4)	C12—H12A	0.9300
N2—N3	1.296 (3)	C13—H13A	0.9300
C17—C18	1.379 (4)	C19—H19A	0.9300
C17—C22	1.382 (3)	C21—H21A	0.9300
C8—C7	1.517 (3)	C23—H23A	0.9600
C8—C9	1.521 (3)	C23—H23B	0.9600
C8—H8A	0.9800	C23—H23C	0.9600
C22—C21	1.378 (4)	C4—C3	1.367 (5)
C22—H22A	0.9300	C4—H4B	0.9300
C15—C14	1.371 (4)	C3—H3B	0.9300
C15—H15A	0.9300

C16—O2—C8	115.37 (18)	C21—C20—C19	117.8 (3)
N2—N1—C10	109.96 (19)	C21—C20—C23	121.2 (3)
N2—N1—C9	120.5 (2)	C19—C20—C23	121.0 (3)
C10—N1—C9	128.9 (2)	C4—C5—C6	120.3 (3)
O3—C16—O2	122.2 (2)	C4—C5—H5A	119.9
O3—C16—C17	125.9 (2)	C6—C5—H5A	119.9
O2—C16—C17	111.9 (2)	C2—C1—C6	120.9 (3)
N1—C10—C11	104.3 (2)	C2—C1—Cl1	118.9 (3)
N1—C10—C15	133.4 (2)	C6—C1—Cl1	120.2 (2)
C11—C10—C15	122.3 (2)	C15—C14—C13	122.3 (3)
C1—C6—C5	119.0 (2)	C15—C14—H14A	118.8
C1—C6—C7	122.1 (2)	C13—C14—H14A	118.8
C5—C6—C7	118.9 (2)	C1—C2—C3	119.2 (3)
N3—C11—C10	108.4 (2)	C1—C2—H2B	120.4
N3—C11—C12	130.9 (3)	C3—C2—H2B	120.4
C10—C11—C12	120.7 (2)	C19—C18—C17	120.3 (3)
N3—N2—N1	109.2 (2)	C19—C18—H18A	119.9
C18—C17—C22	118.8 (3)	C17—C18—H18A	119.9
C18—C17—C16	118.9 (2)	C13—C12—C11	116.9 (3)
C22—C17—C16	122.3 (2)	C13—C12—H12A	121.6
N2—N3—C11	108.2 (2)	C11—C12—H12A	121.6
O2—C8—C7	111.28 (19)	C12—C13—C14	122.1 (3)
O2—C8—C9	106.32 (18)	C12—C13—H13A	118.9
C7—C8—C9	109.72 (19)	C14—C13—H13A	118.9
O2—C8—H8A	109.8	C20—C19—C18	121.4 (3)
C7—C8—H8A	109.8	C20—C19—H19A	119.3
C9—C8—H8A	109.8	C18—C19—H19A	119.3
C21—C22—C17	119.9 (3)	C20—C21—C22	121.8 (3)
C21—C22—H22A	120.0	C20—C21—H21A	119.1
C17—C22—H22A	120.0	C22—C21—H21A	119.1
C14—C15—C10	115.6 (3)	C20—C23—H23A	109.5
C14—C15—H15A	122.2	C20—C23—H23B	109.5
C10—C15—H15A	122.2	H23A—C23—H23B	109.5
O1—C7—C6	122.7 (2)	C20—C23—H23C	109.5
O1—C7—C8	121.8 (2)	H23A—C23—H23C	109.5
C6—C7—C8	115.5 (2)	H23B—C23—H23C	109.5
N1—C9—C8	111.6 (2)	C3—C4—C5	119.6 (3)
N1—C9—H9A	109.3	C3—C4—H4B	120.2
C8—C9—H9A	109.3	C5—C4—H4B	120.2
N1—C9—H9B	109.3	C4—C3—C2	121.0 (3)
C8—C9—H9B	109.3	C4—C3—H3B	119.5
H9A—C9—H9B	108.0	C2—C3—H3B	119.5

C8—O2—C16—O3	1.4 (3)	O2—C8—C7—C6	168.29 (19)
C8—O2—C16—C17	−177.87 (19)	C9—C8—C7—C6	−74.3 (3)
N2—N1—C10—C11	−0.5 (3)	N2—N1—C9—C8	−74.9 (3)
C9—N1—C10—C11	−170.9 (2)	C10—N1—C9—C8	94.6 (3)
N2—N1—C10—C15	179.8 (3)	O2—C8—C9—N1	−53.5 (3)
C9—N1—C10—C15	9.4 (4)	C7—C8—C9—N1	−174.0 (2)
N1—C10—C11—N3	0.2 (3)	C1—C6—C5—C4	−0.1 (4)
C15—C10—C11—N3	179.9 (2)	C7—C6—C5—C4	−177.9 (2)
N1—C10—C11—C12	179.9 (2)	C5—C6—C1—C2	1.0 (4)
C15—C10—C11—C12	−0.4 (4)	C7—C6—C1—C2	178.7 (2)
C10—N1—N2—N3	0.6 (3)	C5—C6—C1—Cl1	178.87 (19)
C9—N1—N2—N3	171.9 (2)	C7—C6—C1—Cl1	−3.4 (3)
O3—C16—C17—C18	4.8 (4)	C10—C15—C14—C13	−0.3 (4)
O2—C16—C17—C18	−176.0 (2)	C6—C1—C2—C3	−1.6 (5)
O3—C16—C17—C22	−175.4 (3)	Cl1—C1—C2—C3	−179.5 (2)
O2—C16—C17—C22	3.8 (3)	C22—C17—C18—C19	−0.9 (4)
N1—N2—N3—C11	−0.4 (3)	C16—C17—C18—C19	178.9 (2)
C10—C11—N3—N2	0.1 (3)	N3—C11—C12—C13	179.2 (3)
C12—C11—N3—N2	−179.5 (3)	C10—C11—C12—C13	−0.4 (4)
C16—O2—C8—C7	−76.5 (2)	C11—C12—C13—C14	0.8 (4)
C16—O2—C8—C9	164.1 (2)	C15—C14—C13—C12	−0.5 (5)
C18—C17—C22—C21	0.2 (4)	C21—C20—C19—C18	0.3 (4)
C16—C17—C22—C21	−179.6 (2)	C23—C20—C19—C18	−179.7 (3)
N1—C10—C15—C14	−179.6 (2)	C17—C18—C19—C20	0.6 (4)
C11—C10—C15—C14	0.7 (4)	C19—C20—C21—C22	−0.9 (4)
C1—C6—C7—O1	−66.6 (3)	C23—C20—C21—C22	179.0 (3)
C5—C6—C7—O1	111.1 (3)	C17—C22—C21—C20	0.7 (4)
C1—C6—C7—C8	112.1 (3)	C6—C5—C4—C3	−0.2 (5)
C5—C6—C7—C8	−70.2 (3)	C5—C4—C3—C2	−0.3 (5)
O2—C8—C7—O1	−12.9 (3)	C1—C2—C3—C4	1.2 (5)
C9—C8—C7—O1	104.5 (3)

Experimental details

Crystal data
Chemical formula	C₂₃H₁₈ClN₃O₃
M_r	419.85
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.9254 (7), 26.151 (2), 10.6002 (9)
β (°)	107.895 (1)
V (Å³)	2090.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.31 × 0.17 × 0.07

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.934, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	11618, 4112, 2671
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.155, 1.02
No. of reflections	4112
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.14

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

π–π and C—H···π interactions top

Cg4 is the centroid of the tolyl ring. Symmetry codes: (i) 2-x, 2-y, 2-z; (ii) x-1, -y+3/2, z-1/2.

	Centroid–centroid (Å)	Interplanar distance (Å)	Slippage (Å)
Cg4···Cg4ⁱ	3.830 (2)	3.705	0.968

	C···Cg (Å)	C—H···Cg (°)	H···Cg (Å)
C2···Cg4ⁱⁱ	3.879 (3)	168	2.96

Acknowledgements

This project was supported by the Natural Science Foundation of Shandong Province (grant No. 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. CrossRef Web of Science Google Scholar
Bi, S., Luo, H., Zeng, W.-L. & Wan, J. (2007). Acta Cryst. E63, o4499. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar