4-(4-Chloro­benzo­yl)-3-methyl-1-phenyl-1H-pyrazol-5-yl 4-chloro­benzoate

Li, X.-X.; Chen, Z.

doi:10.1107/S1600536811048136

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3404

https://doi.org/10.1107/S1600536811048136

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4-(4-Chlorobenzoyl)-3-methyl-1-phenyl-1H-pyrazol-5-yl 4-chlorobenzoate

Xiao-Xia Li ^a ^* and Zhong Chen ^a

^aInstitute of Functional Materials, Jiangxi University of Finance & Economics, Nanchang 330013, People's Republic of China
^*Correspondence e-mail: xiaoxialichen@yahoo.cn

(Received 3 November 2011; accepted 13 November 2011; online 23 November 2011)

In the title compound, C₂₄H₁₆Cl₂N₂O₃, the three benzene rings are twisted with respect to the central pyrazole ring, making dihedral angles of 71.56 (9) (4-chlorobenzoyloxy), 57.55 (8) (4-chlorobenzoyl) and 39.33 (1)° (phenyl).

Related literature

For the antibacterial and biological activity of 5-acyloxypyrazoles, see Bai et al. (2002 ); Varma (1999 ).

Experimental

Crystal data

C₂₄H₁₆Cl₂N₂O₃
M_r = 451.29
Monoclinic, P 2₁ /c
a = 11.4481 (4) Å
b = 29.4169 (13) Å
c = 6.4120 (3) Å
β = 99.669 (3)°
V = 2128.68 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 296 K
0.23 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.930, T_max = 0.948
16531 measured reflections
3765 independent reflections
1884 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.093
S = 1.03
3765 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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 I, global. DOI: https://doi.org/10.1107/S1600536811048136/vm2134sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048136/vm2134Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811048136/vm2134Isup3.cml

checkCIF report

Comment top

5-Acyloxypyrazoles have received considerable attention due to their high antibacterial and biological activities (Bai et al., 2002, Varma, 1999). As part of our ongoing search for biologically active molecules, the title compound was synthesized and characterized by X-ray diffraction (Fig. 1).

The three phenyl rings (C1—C6, r.m.s. deviation = 0.0047 Å; C12—C17, r.m.s. deviation = 0.0061 Å; C19—C24, r.m.s. deviation = 0.0045 Å) are twisted with respect to the central pyrazole ring (N1,2/C8—C10, r.m.s. deviation = 0.0065 Å) making dihedral angles of 71.56 (9)°, 57.55 (8)° and 39.33 (1)°, respectively. As expected, there are no classic hydrogen bonds in the structure.

Related literature top

For the antibacterial and biological activity of 5-acyloxypyrazoles, see Bai et al. (2002); Varma (1999).

Experimental top

1.74 g of 1-phenyl-3-methyl-5-pyrazolone was dissolved in 10 ml dioxane by heating to 80 °C, and 1.5 g of calcium hydroxide was added, then 2 ml of 4-chlorobenzoylchloride was added dropwise within 20 min. After refluxing for 2 h, the reaction mixture was poured into 30 ml diluted hydrochloric acid (3 N). A cream colored powder was obtained by filtration, and used for recrystallization from ethanol to give colorless needle crystals.

Structure description top

For the antibacterial and biological activity of 5-acyloxypyrazoles, see Bai et al. (2002); Varma (1999).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 title molecule with the displacement ellipsoids shown at the 30% probability level.

4-(4-Chlorobenzoyl)-3-methyl-1-phenyl-1H-pyrazol-5-yl 4-chlorobenzoate top

Crystal data top

C₂₄H₁₆Cl₂N₂O₃	F(000) = 928
M_r = 451.29	D_x = 1.408 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1569 reflections
a = 11.4481 (4) Å	θ = 2.8–19.2°
b = 29.4169 (13) Å	µ = 0.33 mm⁻¹
c = 6.4120 (3) Å	T = 296 K
β = 99.669 (3)°	Needle, colorless
V = 2128.68 (16) Å³	0.23 × 0.18 × 0.16 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3765 independent reflections
Radiation source: fine-focus sealed tube	1884 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
φ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −13→13
T_min = 0.930, T_max = 0.948	k = −35→34
16531 measured reflections	l = −7→7

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0199P)² + 0.5P] where P = (F_o² + 2F_c²)/3
3765 reflections	(Δ/σ)_max < 0.001
281 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₄H₁₆Cl₂N₂O₃	V = 2128.68 (16) Å³
M_r = 451.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4481 (4) Å	µ = 0.33 mm⁻¹
b = 29.4169 (13) Å	T = 296 K
c = 6.4120 (3) Å	0.23 × 0.18 × 0.16 mm
β = 99.669 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3765 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1884 reflections with I > 2σ(I)
T_min = 0.930, T_max = 0.948	R_int = 0.067
16531 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.03	Δρ_max = 0.15 e Å⁻³
3765 reflections	Δρ_min = −0.19 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	0.69348 (7)	0.00005 (3)	0.62066 (14)	0.0918 (3)
C1	0.7963 (2)	−0.02529 (11)	0.8140 (5)	0.0605 (8)
C2	0.8162 (3)	−0.00773 (10)	1.0144 (6)	0.0689 (9)
H2A	0.7739	0.0175	1.0469	0.083*
C3	0.8991 (2)	−0.02759 (10)	1.1679 (5)	0.0609 (8)
H3A	0.9118	−0.0160	1.3048	0.073*
C4	0.9635 (2)	−0.06468 (9)	1.1194 (5)	0.0499 (7)
C5	0.9413 (2)	−0.08216 (10)	0.9159 (5)	0.0605 (8)
H5A	0.9832	−0.1074	0.8820	0.073*
C6	0.8580 (3)	−0.06247 (10)	0.7642 (5)	0.0672 (9)
H6A	0.8435	−0.0743	0.6279	0.081*
C7	1.0529 (2)	−0.08436 (9)	1.2859 (5)	0.0530 (8)
C8	1.1952 (2)	−0.14311 (9)	1.3390 (4)	0.0506 (7)
C9	1.1780 (2)	−0.17194 (9)	1.4968 (4)	0.0501 (7)
C10	1.2931 (3)	−0.18817 (9)	1.5767 (4)	0.0550 (8)
C11	1.0674 (3)	−0.18198 (9)	1.5742 (5)	0.0587 (8)
C12	0.9553 (3)	−0.18520 (9)	1.4215 (5)	0.0533 (7)
C13	0.9556 (3)	−0.19948 (9)	1.2166 (5)	0.0580 (8)
H13A	1.0271	−0.2058	1.1722	0.070*
C14	0.8509 (3)	−0.20449 (10)	1.0771 (5)	0.0695 (9)
H14A	0.8512	−0.2146	0.9398	0.083*
C15	0.7463 (3)	−0.19438 (12)	1.1436 (6)	0.0824 (11)
C16	0.7438 (3)	−0.18042 (11)	1.3472 (7)	0.0853 (11)
H16A	0.6721	−0.1739	1.3908	0.102*
C17	0.8479 (3)	−0.17622 (10)	1.4846 (5)	0.0679 (9)
H17A	0.8467	−0.1671	1.6231	0.081*
C18	1.3268 (3)	−0.22254 (10)	1.7484 (5)	0.0731 (9)
H18A	1.4014	−0.2360	1.7344	0.110*
H18C	1.2671	−0.2457	1.7372	0.110*
H18B	1.3334	−0.2079	1.8837	0.110*
C19	1.3721 (3)	−0.11677 (9)	1.1883 (5)	0.0533 (7)
C20	1.4818 (3)	−0.09849 (11)	1.2704 (5)	0.0726 (9)
H20A	1.5152	−0.1028	1.4115	0.087*
C21	1.5397 (3)	−0.07371 (13)	1.1369 (7)	0.0947 (12)
H21A	1.6136	−0.0613	1.1884	0.114*
C22	1.4902 (4)	−0.06699 (12)	0.9297 (7)	0.0928 (12)
H22A	1.5301	−0.0498	0.8422	0.111*
C23	1.3817 (3)	−0.08555 (11)	0.8510 (6)	0.0753 (9)
H23A	1.3482	−0.0810	0.7101	0.090*
C24	1.3226 (3)	−0.11086 (10)	0.9802 (5)	0.0602 (8)
H24A	1.2496	−0.1239	0.9270	0.072*
O1	1.11813 (15)	−0.11725 (6)	1.2022 (3)	0.0523 (5)
O2	1.07060 (18)	−0.07494 (7)	1.4689 (3)	0.0757 (6)
O3	1.06779 (17)	−0.18818 (7)	1.7646 (3)	0.0763 (6)
N1	1.3736 (2)	−0.17134 (8)	1.4732 (4)	0.0589 (7)
N2	1.3115 (2)	−0.14249 (8)	1.3265 (4)	0.0524 (6)
Cl2	0.61559 (9)	−0.19901 (5)	0.9673 (2)	0.1547 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0762 (6)	0.0896 (6)	0.1072 (7)	0.0202 (5)	0.0090 (5)	0.0366 (6)
C1	0.0492 (18)	0.055 (2)	0.077 (2)	0.0040 (15)	0.0114 (18)	0.0182 (19)
C2	0.064 (2)	0.053 (2)	0.094 (3)	0.0148 (17)	0.026 (2)	0.007 (2)
C3	0.067 (2)	0.053 (2)	0.067 (2)	0.0022 (16)	0.0214 (18)	−0.0036 (17)
C4	0.0458 (17)	0.0458 (18)	0.060 (2)	0.0009 (14)	0.0139 (15)	−0.0008 (16)
C5	0.0576 (19)	0.057 (2)	0.066 (2)	0.0128 (15)	0.0060 (17)	−0.0045 (17)
C6	0.066 (2)	0.066 (2)	0.066 (2)	0.0115 (18)	0.0011 (18)	0.0014 (18)
C7	0.0514 (19)	0.0457 (19)	0.064 (2)	−0.0031 (15)	0.0158 (18)	−0.0042 (18)
C8	0.0475 (19)	0.0554 (19)	0.0473 (19)	0.0039 (15)	0.0028 (15)	−0.0034 (16)
C9	0.0492 (18)	0.0528 (18)	0.0465 (19)	−0.0039 (15)	0.0025 (15)	−0.0007 (15)
C10	0.064 (2)	0.0504 (19)	0.0459 (19)	0.0000 (16)	−0.0031 (16)	−0.0006 (15)
C11	0.069 (2)	0.055 (2)	0.052 (2)	−0.0016 (16)	0.0106 (18)	−0.0029 (17)
C12	0.0540 (19)	0.0517 (19)	0.054 (2)	−0.0058 (15)	0.0089 (16)	0.0002 (16)
C13	0.0527 (18)	0.062 (2)	0.058 (2)	−0.0050 (15)	0.0068 (17)	−0.0002 (17)
C14	0.068 (2)	0.071 (2)	0.066 (2)	−0.0045 (18)	0.0012 (19)	−0.0051 (17)
C15	0.055 (2)	0.085 (3)	0.098 (3)	0.0035 (19)	−0.016 (2)	−0.016 (2)
C16	0.056 (2)	0.088 (3)	0.111 (3)	0.0097 (19)	0.011 (2)	−0.014 (2)
C17	0.062 (2)	0.069 (2)	0.074 (2)	0.0028 (17)	0.015 (2)	−0.0066 (18)
C18	0.073 (2)	0.070 (2)	0.070 (2)	0.0026 (17)	−0.0050 (18)	0.0079 (18)
C19	0.0528 (19)	0.0463 (18)	0.064 (2)	−0.0010 (15)	0.0180 (17)	−0.0075 (16)
C20	0.056 (2)	0.081 (2)	0.080 (2)	−0.0097 (18)	0.0120 (19)	−0.011 (2)
C21	0.069 (2)	0.104 (3)	0.116 (4)	−0.034 (2)	0.031 (3)	−0.017 (3)
C22	0.102 (3)	0.081 (3)	0.107 (3)	−0.020 (2)	0.050 (3)	−0.001 (2)
C23	0.091 (3)	0.064 (2)	0.077 (2)	−0.001 (2)	0.031 (2)	0.0006 (19)
C24	0.0638 (19)	0.057 (2)	0.062 (2)	−0.0030 (16)	0.0170 (18)	−0.0064 (17)
O1	0.0490 (11)	0.0569 (12)	0.0507 (12)	0.0087 (10)	0.0076 (10)	0.0031 (10)
O2	0.0890 (15)	0.0802 (16)	0.0559 (14)	0.0158 (12)	0.0069 (13)	−0.0154 (12)
O3	0.0765 (14)	0.0987 (17)	0.0542 (14)	−0.0110 (12)	0.0128 (12)	0.0034 (13)
N1	0.0559 (15)	0.0540 (16)	0.0626 (17)	0.0024 (13)	−0.0020 (14)	0.0010 (13)
N2	0.0463 (15)	0.0524 (15)	0.0580 (16)	0.0006 (12)	0.0073 (13)	−0.0002 (13)
Cl2	0.0745 (7)	0.1987 (13)	0.1694 (12)	0.0168 (7)	−0.0416 (7)	−0.0614 (10)

Geometric parameters (Å, º) top

Cl1—C1	1.728 (3)	C13—C14	1.377 (4)
C1—C2	1.368 (4)	C13—H13A	0.9300
C1—C6	1.369 (4)	C14—C15	1.369 (4)
C2—C3	1.377 (4)	C14—H14A	0.9300
C2—H2A	0.9300	C15—C16	1.374 (4)
C3—C4	1.381 (3)	C15—Cl2	1.723 (3)
C3—H3A	0.9300	C16—C17	1.363 (4)
C4—C5	1.386 (4)	C16—H16A	0.9300
C4—C7	1.468 (4)	C17—H17A	0.9300
C5—C6	1.370 (3)	C18—H18A	0.9600
C5—H5A	0.9300	C18—H18C	0.9600
C6—H6A	0.9300	C18—H18B	0.9600
C7—O2	1.189 (3)	C19—C24	1.370 (4)
C7—O1	1.384 (3)	C19—C20	1.386 (4)
C8—N2	1.348 (3)	C19—N2	1.430 (3)
C8—C9	1.359 (3)	C20—C21	1.376 (4)
C8—O1	1.366 (3)	C20—H20A	0.9300
C9—C10	1.414 (3)	C21—C22	1.368 (4)
C9—C11	1.466 (4)	C21—H21A	0.9300
C10—N1	1.319 (3)	C22—C23	1.373 (4)
C10—C18	1.496 (4)	C22—H22A	0.9300
C11—O3	1.233 (3)	C23—C24	1.374 (4)
C11—C12	1.481 (4)	C23—H23A	0.9300
C12—C13	1.380 (4)	C24—H24A	0.9300
C12—C17	1.383 (4)	N1—N2	1.373 (3)

C2—C1—C6	120.6 (3)	C15—C14—H14A	120.5
C2—C1—Cl1	119.8 (3)	C13—C14—H14A	120.5
C6—C1—Cl1	119.6 (3)	C14—C15—C16	121.3 (3)
C1—C2—C3	119.8 (3)	C14—C15—Cl2	119.2 (3)
C1—C2—H2A	120.1	C16—C15—Cl2	119.5 (3)
C3—C2—H2A	120.1	C17—C16—C15	119.0 (3)
C2—C3—C4	120.2 (3)	C17—C16—H16A	120.5
C2—C3—H3A	119.9	C15—C16—H16A	120.5
C4—C3—H3A	119.9	C16—C17—C12	121.2 (3)
C3—C4—C5	119.0 (3)	C16—C17—H17A	119.4
C3—C4—C7	118.7 (3)	C12—C17—H17A	119.4
C5—C4—C7	122.2 (3)	C10—C18—H18A	109.5
C6—C5—C4	120.5 (3)	C10—C18—H18C	109.5
C6—C5—H5A	119.8	H18A—C18—H18C	109.5
C4—C5—H5A	119.8	C10—C18—H18B	109.5
C5—C6—C1	119.8 (3)	H18A—C18—H18B	109.5
C5—C6—H6A	120.1	H18C—C18—H18B	109.5
C1—C6—H6A	120.1	C24—C19—C20	121.4 (3)
O2—C7—O1	122.1 (3)	C24—C19—N2	120.4 (3)
O2—C7—C4	127.4 (3)	C20—C19—N2	118.2 (3)
O1—C7—C4	110.4 (3)	C21—C20—C19	118.0 (3)
N2—C8—C9	108.7 (2)	C21—C20—H20A	121.0
N2—C8—O1	119.5 (3)	C19—C20—H20A	121.0
C9—C8—O1	131.8 (3)	C22—C21—C20	121.1 (3)
C8—C9—C10	103.7 (3)	C22—C21—H21A	119.5
C8—C9—C11	128.2 (3)	C20—C21—H21A	119.5
C10—C9—C11	127.9 (3)	C21—C22—C23	120.1 (4)
N1—C10—C9	112.2 (3)	C21—C22—H22A	120.0
N1—C10—C18	120.5 (3)	C23—C22—H22A	120.0
C9—C10—C18	127.1 (3)	C24—C23—C22	120.0 (3)
O3—C11—C9	120.3 (3)	C24—C23—H23A	120.0
O3—C11—C12	120.3 (3)	C22—C23—H23A	120.0
C9—C11—C12	119.4 (3)	C19—C24—C23	119.4 (3)
C13—C12—C17	118.8 (3)	C19—C24—H24A	120.3
C13—C12—C11	120.6 (3)	C23—C24—H24A	120.3
C17—C12—C11	120.6 (3)	C8—O1—C7	118.2 (2)
C14—C13—C12	120.6 (3)	C10—N1—N2	104.6 (2)
C14—C13—H13A	119.7	C8—N2—N1	110.7 (2)
C12—C13—H13A	119.7	C8—N2—C19	129.1 (2)
C15—C14—C13	119.1 (3)	N1—N2—C19	120.2 (2)

C6—C1—C2—C3	0.0 (4)	C12—C13—C14—C15	1.1 (4)
Cl1—C1—C2—C3	−179.2 (2)	C13—C14—C15—C16	−1.6 (5)
C1—C2—C3—C4	1.0 (4)	C13—C14—C15—Cl2	178.1 (2)
C2—C3—C4—C5	−1.5 (4)	C14—C15—C16—C17	0.6 (5)
C2—C3—C4—C7	178.7 (2)	Cl2—C15—C16—C17	−179.0 (2)
C3—C4—C5—C6	1.0 (4)	C15—C16—C17—C12	0.8 (5)
C7—C4—C5—C6	−179.2 (3)	C13—C12—C17—C16	−1.3 (4)
C4—C5—C6—C1	0.0 (4)	C11—C12—C17—C16	−177.9 (3)
C2—C1—C6—C5	−0.5 (4)	C24—C19—C20—C21	0.6 (4)
Cl1—C1—C6—C5	178.7 (2)	N2—C19—C20—C21	−179.9 (3)
C3—C4—C7—O2	7.8 (4)	C19—C20—C21—C22	0.5 (5)
C5—C4—C7—O2	−171.9 (3)	C20—C21—C22—C23	−0.8 (6)
C3—C4—C7—O1	−172.5 (2)	C21—C22—C23—C24	0.1 (5)
C5—C4—C7—O1	7.8 (3)	C20—C19—C24—C23	−1.3 (4)
N2—C8—C9—C10	0.1 (3)	N2—C19—C24—C23	179.2 (2)
O1—C8—C9—C10	179.6 (3)	C22—C23—C24—C19	1.0 (4)
N2—C8—C9—C11	177.1 (3)	N2—C8—O1—C7	−120.0 (3)
O1—C8—C9—C11	−3.5 (5)	C9—C8—O1—C7	60.6 (4)
C8—C9—C10—N1	−1.2 (3)	O2—C7—O1—C8	7.8 (4)
C11—C9—C10—N1	−178.2 (3)	C4—C7—O1—C8	−171.9 (2)
C8—C9—C10—C18	−177.5 (3)	C9—C10—N1—N2	1.7 (3)
C11—C9—C10—C18	5.5 (5)	C18—C10—N1—N2	178.3 (2)
C8—C9—C11—O3	−142.7 (3)	C9—C8—N2—N1	0.9 (3)
C10—C9—C11—O3	33.6 (4)	O1—C8—N2—N1	−178.6 (2)
C8—C9—C11—C12	38.1 (4)	C9—C8—N2—C19	−178.7 (2)
C10—C9—C11—C12	−145.7 (3)	O1—C8—N2—C19	1.8 (4)
O3—C11—C12—C13	−149.5 (3)	C10—N1—N2—C8	−1.6 (3)
C9—C11—C12—C13	29.7 (4)	C10—N1—N2—C19	178.0 (2)
O3—C11—C12—C17	27.1 (4)	C24—C19—N2—C8	−40.2 (4)
C9—C11—C12—C17	−153.6 (3)	C20—C19—N2—C8	140.2 (3)
C17—C12—C13—C14	0.3 (4)	C24—C19—N2—N1	140.2 (3)
C11—C12—C13—C14	177.0 (3)	C20—C19—N2—N1	−39.3 (3)

Experimental details

Crystal data
Chemical formula	C₂₄H₁₆Cl₂N₂O₃
M_r	451.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.4481 (4), 29.4169 (13), 6.4120 (3)
β (°)	99.669 (3)
V (Å³)	2128.68 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.23 × 0.18 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.930, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	16531, 3765, 1884
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.093, 1.03
No. of reflections	3765
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.19

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors are grateful to the Natural Science Foundation of Jiangxi Province for financial support (No. 2010GQS0064).

References

Bai, Y. J., Lu, J., Gan, H. Y., Wang, Z. J. & Ma, H. R. (2002). Chin. J. Org. Chem. 22, 638–641. CAS Google Scholar
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA . Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Varma, R. S. (1999). J. Heterocycl. Chem. 36, 1565–1571. CrossRef CAS Google Scholar