3-[5-(2,4-Dichloro­phen­yl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-4-hy­droxy-2H-chromen-2-one

Asad, M.; Oo, C.-W.; Osman, H.; Rosli, M.M.; Fun, H.-K.

doi:10.1107/S1600536811001590

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o437-o438

doi:10.1107/S1600536811001590

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3-[5-(2,4-Dichlorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-4-hydroxy-2H-chromen-2-one

Mohammad Asad,^a Chuan-Wei Oo,^a ‡ Hasnah Osman,^a Mohd Mustaqim Rosli ^b and Hoong-Kun Fun ^b ^*§

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 28 December 2010; accepted 11 January 2011; online 22 January 2011)

In the title compound, C₂₄H₁₆Cl₂N₂O₃, the chromene ring system is almost planar, with a maximum deviation of 0.042 (1) Å. It makes dihedral angles of 3.72 (6), 73.37 (5) and 12.00 (5)° with the dihydropyrazole, benzene and phenyl rings, respectively. An intramolecular O—H⋯N hydrogen bond forms an S(6) ring motif. In the crystal, molecules are linked via C—H⋯O interactions, forming an infinite chain along the a axis. The crystal packing is further stabilized by a π–π stacking interaction [centroid–centroid distance = 3.5471 (7) Å] and a Cl⋯Cl short contact [Cl⋯Cl = 3.214 (1) Å].

Related literature

For a related structure, see: Asad et al. (2010 ). For the biological activity of pyrazoline derivatives, see: Bernstein et al. (1947 ); Chimenti et al. (2004 ); Goodell et al. (2006 ); Hollis et al. (1984 ); Mohammad et al. (2008 ); Siddiqui et al. (2008 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₄H₁₆Cl₂N₂O₃
M_r = 451.29
Triclinic, $[P \overline 1]$
a = 6.2583 (2) Å
b = 11.5136 (5) Å
c = 14.2248 (5) Å
α = 87.242 (1)°
β = 88.821 (1)°
γ = 76.181 (1)°
V = 994.11 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 100 K
0.46 × 0.15 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.852, T_max = 0.955
22849 measured reflections
5747 independent reflections
5151 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.106
S = 1.03
5747 reflections
284 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.11 e Å⁻³
Δρ_min = −0.88 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯N1	0.86 (2)	1.80 (3)	2.5655 (14)	148 (2)
C14—H14A⋯O2ⁱ	0.93	2.40	3.2747 (17)	157
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001590/is2660sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001590/is2660Isup2.hkl

checkCIF report

Comment top

In our earlier work we have reported the crystal structure of chalcone (Asad et al., 2010). In continuation of our work, we reported here the crystal structure of pyrazoline (title compound) which was afforded by the condensation of chalcone with phenylhydrazine. A large number of pyrazoline derivatives showed a broad range of biological properties such as antibacterial (Siddiqui et al., 2008), antiviral (Goodell et al., 2006), antiparasitic (Bernstein et al., 1947), anti-inflammatory (Mohammad et al., 2008), antidepressant (Chimenti et al., 2004) and anticancer (Hollis et al., 1984) activities.

All geometrical parameters of the title compound, (I), are within normal ranges. The chromene group is almost planar with a maximum deviation of 0.042 (1) Å for atom C1. It makes dihedral angles of 3.72 (6), 73.37 (5) and 12.00 (5)° with C10-C12/N1-N1 pyrazole and C13-C18 benzene and C19-C24 phenyl rings, respectively. An intramolecular interaction of O3—H1O3···N1 (Table 1) forms an S(6) hydrogen ring motif.

In the crystal structure, the molecules are linked via C14—H14···O2ⁱ (Table 1) to form infinite chains along the a axis. The crystal packing is further stabilized by π–π stacking interactions with Cg–Cg distance of 3.5471 (7) Å (Cg = centroid of O1/C1-C2/C7-C9) together with Cl1···Cl1 short contact [Cl1···Cl1(1-x, 2-y, -z) = 3.214 (1) Å].

Related literature top

For a related structure, see: Asad et al. (2010). For the biological activity of pyrazoline derivatives, see: Bernstein et al. (1947); Chimenti et al. (2004); Goodell et al. (2006); Hollis et al. (1984); Mohammad et al. (2008); Siddiqui et al. (2008). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The compound, 3-[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]-4-hydroxy-2H-chromen-2-one (2.76 mmol, 1.00 g) was dissolved in acetic acid (20 ml) and phenylhydrazine (2.76 mmol, 0.30 g) was added to it. The reaction mixture was refluxed on a heating mantle for 2 h. After the reaction was over, the reaction mixture was cooled to room temperature and poured into ice cold water. The yellow-colour solid formed was filtered, washed with water, dried and recrystallized from chloroform-methanol (80:20 v/v) to get the pure title compound in 62.5% yield.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal packing of the title compound viewed along the c axis, showing a molecular chain along the a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.

3-[5-(2,4-Dichlorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-4- hydroxy-2H-chromen-2-one top

Crystal data top

C₂₄H₁₆Cl₂N₂O₃	Z = 2
M_r = 451.29	F(000) = 464
Triclinic, P1	D_x = 1.508 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2583 (2) Å	Cell parameters from 9965 reflections
b = 11.5136 (5) Å	θ = 2.3–32.7°
c = 14.2248 (5) Å	µ = 0.36 mm⁻¹
α = 87.242 (1)°	T = 100 K
β = 88.821 (1)°	Block, yellow
γ = 76.181 (1)°	0.46 × 0.15 × 0.13 mm
V = 994.11 (6) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5747 independent reflections
Radiation source: fine-focus sealed tube	5151 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.852, T_max = 0.955	k = −16→16
22849 measured reflections	l = −20→18

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0484P)² + 0.7425P] where P = (F_o² + 2F_c²)/3
5747 reflections	(Δ/σ)_max = 0.001
284 parameters	Δρ_max = 1.11 e Å⁻³
0 restraints	Δρ_min = −0.88 e Å⁻³

Crystal data top

C₂₄H₁₆Cl₂N₂O₃	γ = 76.181 (1)°
M_r = 451.29	V = 994.11 (6) Å³
Triclinic, P1	Z = 2
a = 6.2583 (2) Å	Mo Kα radiation
b = 11.5136 (5) Å	µ = 0.36 mm⁻¹
c = 14.2248 (5) Å	T = 100 K
α = 87.242 (1)°	0.46 × 0.15 × 0.13 mm
β = 88.821 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5747 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5151 reflections with I > 2σ(I)
T_min = 0.852, T_max = 0.955	R_int = 0.020
22849 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 1.11 e Å⁻³
5747 reflections	Δρ_min = −0.88 e Å⁻³
284 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.35949 (7)	0.90740 (4)	0.03853 (2)	0.03009 (10)
Cl2	−0.14981 (8)	0.62457 (3)	−0.06976 (3)	0.03714 (11)
O1	0.71612 (15)	0.58755 (9)	0.51861 (7)	0.01973 (19)
O2	0.72747 (16)	0.66920 (10)	0.37635 (7)	0.0251 (2)
O3	0.06651 (15)	0.75993 (9)	0.55672 (7)	0.02046 (19)
N1	0.07093 (17)	0.86134 (9)	0.39234 (7)	0.0162 (2)
N2	−0.00154 (18)	0.92564 (10)	0.31061 (7)	0.0192 (2)
C1	0.6146 (2)	0.66136 (11)	0.44534 (9)	0.0177 (2)
C2	0.6117 (2)	0.57587 (11)	0.60307 (9)	0.0173 (2)
C3	0.7375 (2)	0.50505 (11)	0.67383 (10)	0.0205 (2)
H3A	0.8836	0.4664	0.6630	0.025*
C4	0.6386 (2)	0.49384 (12)	0.76082 (10)	0.0217 (3)
H4A	0.7202	0.4476	0.8091	0.026*
C5	0.4182 (2)	0.55092 (12)	0.77721 (9)	0.0218 (3)
H5A	0.3550	0.5431	0.8362	0.026*
C6	0.2942 (2)	0.61889 (12)	0.70583 (9)	0.0203 (2)
H6A	0.1469	0.6555	0.7164	0.024*
C7	0.3911 (2)	0.63252 (11)	0.61735 (9)	0.0170 (2)
C8	0.2763 (2)	0.70665 (11)	0.54083 (9)	0.0164 (2)
C9	0.38412 (19)	0.72235 (11)	0.45724 (8)	0.0156 (2)
C10	0.2732 (2)	0.80047 (11)	0.38073 (8)	0.0153 (2)
C11	0.3638 (2)	0.82338 (11)	0.28433 (9)	0.0168 (2)
H11A	0.4255	0.7491	0.2538	0.020*
H11B	0.4754	0.8688	0.2875	0.020*
C12	0.1564 (2)	0.89691 (11)	0.23291 (8)	0.0157 (2)
H12A	0.1858	0.9707	0.2043	0.019*
C13	0.07859 (19)	0.82708 (11)	0.15820 (9)	0.0153 (2)
C14	−0.0757 (2)	0.75932 (11)	0.17822 (10)	0.0199 (2)
H14A	−0.1327	0.7566	0.2390	0.024*
C15	−0.1455 (2)	0.69604 (12)	0.10939 (11)	0.0248 (3)
H15A	−0.2486	0.6514	0.1237	0.030*
C16	−0.0596 (2)	0.69996 (12)	0.01883 (10)	0.0244 (3)
C17	0.0968 (2)	0.76382 (12)	−0.00390 (10)	0.0243 (3)
H17A	0.1558	0.7648	−0.0644	0.029*
C18	0.1630 (2)	0.82658 (12)	0.06681 (9)	0.0189 (2)
C19	−0.2083 (2)	1.00293 (10)	0.30513 (8)	0.0154 (2)
C20	−0.3406 (2)	1.03064 (11)	0.38552 (9)	0.0177 (2)
H20A	−0.2880	0.9997	0.4444	0.021*
C21	−0.5506 (2)	1.10448 (12)	0.37687 (9)	0.0201 (2)
H21A	−0.6383	1.1216	0.4304	0.024*
C22	−0.6326 (2)	1.15338 (12)	0.28987 (10)	0.0212 (2)
H22A	−0.7743	1.2018	0.2848	0.025*
C23	−0.4991 (2)	1.12856 (12)	0.21073 (9)	0.0207 (2)
H23A	−0.5509	1.1623	0.1524	0.025*
C24	−0.2890 (2)	1.05397 (11)	0.21745 (9)	0.0186 (2)
H24A	−0.2017	1.0379	0.1637	0.022*
H1O3	0.016 (4)	0.804 (2)	0.5079 (18)	0.048 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0363 (2)	0.0397 (2)	0.01977 (16)	−0.02068 (16)	0.01019 (13)	−0.00255 (13)
Cl2	0.0479 (2)	0.02154 (17)	0.0407 (2)	−0.00267 (15)	−0.02561 (18)	−0.00634 (14)
O1	0.0146 (4)	0.0231 (4)	0.0190 (4)	0.0003 (3)	−0.0009 (3)	−0.0002 (3)
O2	0.0161 (4)	0.0323 (5)	0.0233 (5)	0.0001 (4)	0.0039 (4)	0.0024 (4)
O3	0.0141 (4)	0.0267 (5)	0.0172 (4)	0.0011 (3)	0.0017 (3)	0.0027 (4)
N1	0.0159 (5)	0.0181 (5)	0.0129 (4)	−0.0009 (4)	−0.0002 (4)	0.0001 (4)
N2	0.0168 (5)	0.0244 (5)	0.0121 (5)	0.0032 (4)	0.0022 (4)	0.0013 (4)
C1	0.0146 (5)	0.0193 (5)	0.0181 (5)	−0.0016 (4)	−0.0010 (4)	−0.0018 (4)
C2	0.0175 (5)	0.0167 (5)	0.0172 (5)	−0.0027 (4)	−0.0019 (4)	−0.0023 (4)
C3	0.0196 (6)	0.0174 (5)	0.0229 (6)	−0.0005 (4)	−0.0054 (5)	−0.0025 (4)
C4	0.0268 (6)	0.0166 (5)	0.0206 (6)	−0.0024 (5)	−0.0073 (5)	0.0002 (4)
C5	0.0267 (6)	0.0199 (6)	0.0178 (6)	−0.0039 (5)	−0.0007 (5)	0.0007 (4)
C6	0.0196 (6)	0.0206 (6)	0.0190 (6)	−0.0022 (5)	0.0004 (4)	0.0011 (4)
C7	0.0169 (5)	0.0166 (5)	0.0168 (5)	−0.0024 (4)	−0.0015 (4)	−0.0008 (4)
C8	0.0144 (5)	0.0168 (5)	0.0172 (5)	−0.0019 (4)	−0.0009 (4)	−0.0016 (4)
C9	0.0132 (5)	0.0175 (5)	0.0153 (5)	−0.0019 (4)	−0.0006 (4)	−0.0021 (4)
C10	0.0140 (5)	0.0170 (5)	0.0147 (5)	−0.0033 (4)	0.0003 (4)	−0.0024 (4)
C11	0.0140 (5)	0.0205 (5)	0.0156 (5)	−0.0035 (4)	0.0008 (4)	−0.0015 (4)
C12	0.0149 (5)	0.0176 (5)	0.0139 (5)	−0.0028 (4)	0.0021 (4)	−0.0011 (4)
C13	0.0135 (5)	0.0155 (5)	0.0157 (5)	−0.0013 (4)	0.0001 (4)	−0.0001 (4)
C14	0.0157 (5)	0.0183 (5)	0.0249 (6)	−0.0031 (4)	0.0022 (5)	0.0005 (5)
C15	0.0178 (6)	0.0176 (6)	0.0392 (8)	−0.0047 (5)	−0.0043 (5)	−0.0005 (5)
C16	0.0274 (7)	0.0161 (5)	0.0281 (7)	−0.0003 (5)	−0.0130 (5)	−0.0035 (5)
C17	0.0325 (7)	0.0220 (6)	0.0167 (6)	−0.0026 (5)	−0.0037 (5)	−0.0017 (5)
C18	0.0207 (6)	0.0201 (6)	0.0162 (5)	−0.0055 (5)	0.0006 (4)	0.0003 (4)
C19	0.0154 (5)	0.0144 (5)	0.0156 (5)	−0.0018 (4)	0.0003 (4)	−0.0015 (4)
C20	0.0188 (6)	0.0183 (5)	0.0148 (5)	−0.0020 (4)	0.0012 (4)	−0.0016 (4)
C21	0.0191 (6)	0.0199 (6)	0.0197 (6)	−0.0011 (5)	0.0041 (4)	−0.0029 (4)
C22	0.0176 (6)	0.0195 (6)	0.0240 (6)	0.0010 (4)	0.0001 (5)	−0.0018 (5)
C23	0.0218 (6)	0.0192 (6)	0.0184 (6)	0.0003 (5)	−0.0024 (5)	0.0007 (4)
C24	0.0202 (6)	0.0178 (5)	0.0157 (5)	−0.0005 (4)	0.0013 (4)	−0.0001 (4)

Geometric parameters (Å, º) top

Cl1—C18	1.7408 (14)	C11—C12	1.5464 (17)
Cl2—C16	1.7402 (14)	C11—H11A	0.9700
O1—C2	1.3720 (16)	C11—H11B	0.9700
O1—C1	1.3770 (15)	C12—C13	1.5175 (17)
O2—C1	1.2097 (16)	C12—H12A	0.9800
O3—C8	1.3294 (15)	C13—C18	1.3929 (17)
O3—H1O3	0.86 (3)	C13—C14	1.3958 (17)
N1—C10	1.3037 (16)	C14—C15	1.385 (2)
N1—N2	1.3726 (14)	C14—H14A	0.9300
N2—C19	1.3857 (15)	C15—C16	1.388 (2)
N2—C12	1.4634 (15)	C15—H15A	0.9300
C1—C9	1.4560 (17)	C16—C17	1.383 (2)
C2—C3	1.3944 (17)	C17—C18	1.3911 (18)
C2—C7	1.3946 (17)	C17—H17A	0.9300
C3—C4	1.386 (2)	C19—C20	1.4019 (17)
C3—H3A	0.9300	C19—C24	1.4033 (17)
C4—C5	1.399 (2)	C20—C21	1.3884 (18)
C4—H4A	0.9300	C20—H20A	0.9300
C5—C6	1.3828 (18)	C21—C22	1.3904 (19)
C5—H5A	0.9300	C21—H21A	0.9300
C6—C7	1.4041 (18)	C22—C23	1.3876 (19)
C6—H6A	0.9300	C22—H22A	0.9300
C7—C8	1.4420 (17)	C23—C24	1.3907 (18)
C8—C9	1.3807 (17)	C23—H23A	0.9300
C9—C10	1.4540 (17)	C24—H24A	0.9300
C10—C11	1.5085 (17)

C2—O1—C1	122.30 (10)	N2—C12—C13	112.71 (10)
C8—O3—H1O3	108.6 (17)	N2—C12—C11	102.00 (9)
C10—N1—N2	109.48 (10)	C13—C12—C11	112.55 (10)
N1—N2—C19	121.38 (10)	N2—C12—H12A	109.8
N1—N2—C12	112.49 (10)	C13—C12—H12A	109.8
C19—N2—C12	126.03 (10)	C11—C12—H12A	109.8
O2—C1—O1	116.12 (11)	C18—C13—C14	117.41 (12)
O2—C1—C9	125.99 (12)	C18—C13—C12	120.73 (11)
O1—C1—C9	117.88 (11)	C14—C13—C12	121.85 (11)
O1—C2—C3	116.69 (11)	C15—C14—C13	121.30 (13)
O1—C2—C7	121.53 (11)	C15—C14—H14A	119.4
C3—C2—C7	121.78 (12)	C13—C14—H14A	119.4
C4—C3—C2	118.17 (12)	C14—C15—C16	119.24 (13)
C4—C3—H3A	120.9	C14—C15—H15A	120.4
C2—C3—H3A	120.9	C16—C15—H15A	120.4
C3—C4—C5	121.11 (12)	C17—C16—C15	121.55 (12)
C3—C4—H4A	119.4	C17—C16—Cl2	118.24 (12)
C5—C4—H4A	119.4	C15—C16—Cl2	120.21 (11)
C6—C5—C4	120.11 (13)	C16—C17—C18	117.73 (13)
C6—C5—H5A	119.9	C16—C17—H17A	121.1
C4—C5—H5A	119.9	C18—C17—H17A	121.1
C5—C6—C7	119.86 (12)	C17—C18—C13	122.74 (12)
C5—C6—H6A	120.1	C17—C18—Cl1	117.93 (10)
C7—C6—H6A	120.1	C13—C18—Cl1	119.33 (10)
C2—C7—C6	118.95 (11)	N2—C19—C20	121.34 (11)
C2—C7—C8	117.75 (11)	N2—C19—C24	119.68 (11)
C6—C7—C8	123.25 (11)	C20—C19—C24	118.98 (11)
O3—C8—C9	122.99 (11)	C21—C20—C19	119.77 (12)
O3—C8—C7	116.36 (11)	C21—C20—H20A	120.1
C9—C8—C7	120.63 (11)	C19—C20—H20A	120.1
C8—C9—C10	121.34 (11)	C20—C21—C22	121.39 (12)
C8—C9—C1	119.77 (11)	C20—C21—H21A	119.3
C10—C9—C1	118.88 (11)	C22—C21—H21A	119.3
N1—C10—C9	119.64 (11)	C23—C22—C21	118.75 (12)
N1—C10—C11	112.43 (10)	C23—C22—H22A	120.6
C9—C10—C11	127.92 (11)	C21—C22—H22A	120.6
C10—C11—C12	102.04 (9)	C22—C23—C24	120.94 (12)
C10—C11—H11A	111.4	C22—C23—H23A	119.5
C12—C11—H11A	111.4	C24—C23—H23A	119.5
C10—C11—H11B	111.4	C23—C24—C19	120.14 (12)
C12—C11—H11B	111.4	C23—C24—H24A	119.9
H11A—C11—H11B	109.2	C19—C24—H24A	119.9

C10—N1—N2—C19	−176.79 (11)	C9—C10—C11—C12	171.31 (12)
C10—N1—N2—C12	6.61 (15)	N1—N2—C12—C13	109.17 (12)
C2—O1—C1—O2	176.03 (12)	C19—N2—C12—C13	−67.25 (16)
C2—O1—C1—C9	−4.01 (17)	N1—N2—C12—C11	−11.76 (13)
C1—O1—C2—C3	−175.51 (11)	C19—N2—C12—C11	171.82 (12)
C1—O1—C2—C7	4.23 (18)	C10—C11—C12—N2	11.62 (12)
O1—C2—C3—C4	178.39 (11)	C10—C11—C12—C13	−109.42 (11)
C7—C2—C3—C4	−1.36 (19)	N2—C12—C13—C18	157.95 (11)
C2—C3—C4—C5	0.6 (2)	C11—C12—C13—C18	−87.35 (14)
C3—C4—C5—C6	0.7 (2)	N2—C12—C13—C14	−23.34 (16)
C4—C5—C6—C7	−1.3 (2)	C11—C12—C13—C14	91.36 (14)
O1—C2—C7—C6	−178.93 (12)	C18—C13—C14—C15	−1.30 (19)
C3—C2—C7—C6	0.81 (19)	C12—C13—C14—C15	179.95 (11)
O1—C2—C7—C8	−1.45 (18)	C13—C14—C15—C16	0.2 (2)
C3—C2—C7—C8	178.28 (11)	C14—C15—C16—C17	1.2 (2)
C5—C6—C7—C2	0.53 (19)	C14—C15—C16—Cl2	−178.28 (10)
C5—C6—C7—C8	−176.79 (12)	C15—C16—C17—C18	−1.3 (2)
C2—C7—C8—O3	−179.67 (11)	Cl2—C16—C17—C18	178.16 (10)
C6—C7—C8—O3	−2.31 (18)	C16—C17—C18—C13	0.1 (2)
C2—C7—C8—C9	−1.31 (18)	C16—C17—C18—Cl1	−179.87 (10)
C6—C7—C8—C9	176.04 (12)	C14—C13—C18—C17	1.17 (19)
O3—C8—C9—C10	0.68 (19)	C12—C13—C18—C17	179.93 (12)
C7—C8—C9—C10	−177.57 (11)	C14—C13—C18—Cl1	−178.87 (9)
O3—C8—C9—C1	179.66 (11)	C12—C13—C18—Cl1	−0.10 (16)
C7—C8—C9—C1	1.41 (18)	N1—N2—C19—C20	8.45 (19)
O2—C1—C9—C8	−178.87 (13)	C12—N2—C19—C20	−175.43 (12)
O1—C1—C9—C8	1.18 (18)	N1—N2—C19—C24	−170.94 (11)
O2—C1—C9—C10	0.1 (2)	C12—N2—C19—C24	5.18 (19)
O1—C1—C9—C10	−179.82 (11)	N2—C19—C20—C21	−177.32 (12)
N2—N1—C10—C9	−178.26 (11)	C24—C19—C20—C21	2.08 (18)
N2—N1—C10—C11	2.11 (14)	C19—C20—C21—C22	−0.9 (2)
C8—C9—C10—N1	3.12 (18)	C20—C21—C22—C23	−0.9 (2)
C1—C9—C10—N1	−175.87 (11)	C21—C22—C23—C24	1.5 (2)
C8—C9—C10—C11	−177.31 (12)	C22—C23—C24—C19	−0.3 (2)
C1—C9—C10—C11	3.70 (19)	N2—C19—C24—C23	177.91 (12)
N1—C10—C11—C12	−9.10 (13)	C20—C19—C24—C23	−1.49 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N1	0.86 (2)	1.80 (3)	2.5655 (14)	148 (2)
C14—H14A···O2ⁱ	0.93	2.40	3.2747 (17)	157

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₆Cl₂N₂O₃
M_r	451.29
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.2583 (2), 11.5136 (5), 14.2248 (5)
α, β, γ (°)	87.242 (1), 88.821 (1), 76.181 (1)
V (Å³)	994.11 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.46 × 0.15 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.852, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	22849, 5747, 5151
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.106, 1.03
No. of reflections	5747
No. of parameters	284
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.11, −0.88

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N1	0.86 (2)	1.80 (3)	2.5655 (14)	148 (2)
C14—H14A···O2ⁱ	0.93	2.40	3.2747 (17)	157

Symmetry code: (i) x−1, y, z.

Footnotes

‡Additional correspondence author, e-mail: oocw@usm.my.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors are thankful to Universiti Sains Malaysia (USM) for providing necessary research facilities and RU research funding under grant No. 1001/PKIMIA/811134. MA also thanks USM for the award of a postdoctoral fellowship. HKF and MMR thank USM for the Research University Grant (No. 1001/PFIZIK/811160).

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