1-(3-Chloro­phen­yl)-5-(2,4-di­hydroxy­benzo­yl)pyridin-2(1H)-one

Ren, F.; Li, G.; Zhang, Q.; Yao, J.; Zhang, X.

doi:10.1107/S1600536813009689

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o732

https://doi.org/10.1107/S1600536813009689

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1-(3-Chlorophenyl)-5-(2,4-dihydroxybenzoyl)pyridin-2(1H)-one

Fang Ren,^a ^* Guifeng Li,^a Quanying Zhang,^a Jinhua Yao ^a and Xuli Zhang ^a

^aThe First Affiliated Hospital of Xinxiang Medical University, Weihui 453100, Henan Province, People's Republic of China
^*Correspondence e-mail: RenFang788@163.com

(Received 12 December 2012; accepted 9 April 2013; online 13 April 2013)

The chlorophenyl group of the title compound, C₁₈H₁₂ClNO₄, is disordered over two orientations with occupancies of 0.331 (8) and 0.669 (8). An intramolecular hydrogen bond is formed between a hydroxy group and the acyclic carbonyl group. In the crystal, molecules are linked into chains along [110] by O—H⋯O and C—H⋯O hydrogen bonds, forming a ladder motif.

Related literature

For similar structures, see: Ravinder et al. (2012 ); Sengupta et al. (2012 ). For the synthesis, see: Chen et al. (2011 ); Kim & Hong (2011 ). For the biological activity of similar structures, see: Kim et al. (2010 ).

Experimental

Crystal data

C₁₈H₁₂ClNO₄
M_r = 341.74
Triclinic, $[P \overline 1]$
a = 6.689 (3) Å
b = 9.009 (4) Å
c = 13.257 (6) Å
α = 87.193 (5)°
β = 87.719 (5)°
γ = 82.674 (5)°
V = 791.0 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 293 K
0.15 × 0.12 × 0.05 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.962, T_max = 0.987
3286 measured reflections
2726 independent reflections
1929 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.078
wR(F²) = 0.233
S = 1.00
2726 reflections
236 parameters
48 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.91 (4)	1.75 (4)	2.587 (3)	152 (3)
O1—H1⋯O4ⁱ	0.87 (5)	1.79 (5)	2.655 (3)	175 (4)
C3—H3⋯O4ⁱ	0.93	2.50	3.165 (3)	129
C15—H15⋯O1ⁱⁱ	0.93	2.71	3.37 (2)	129
Symmetry codes: (i) x-1, y-1, z; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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/S1600536813009689/fy2085sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S1600536813009689/fy2085Isup2.cdx

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813009689/fy2085Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813009689/fy2085Isup4.cml

checkCIF report

Comment top

The title compound was prepared during our ongoing research on anticancer compounds. It is one of a limited number of reported crystal structures of 2-pyridone derivatives. The structure was confirmed by X-ray crystallography as shown in Fig. 1. H-bonding interactions play a decisive role in the crystal packing arrangement (Fig. 2). Intermolecular C3—H3···O4 and O1—H1···O4 contacts form a supramolecular chain parallel with [110]. Pairs of these chains are linked via C15—H15···O1 interactions to form a ladder motif.

Related literature top

For similar structures, see: Ravinder et al. (2012); Sengupta et al. (2012). For the synthesis, see: Chen et al. (2011); Kim & Hong (2011). For the biological activity of similar structures, see: Kim et al. (2010).

Experimental top

A solution of 7-methoxy-chromen-4-one (0.015 mol) in methanol (150 ml) was added dropwise to a solution of piperidine (0.030 mol) and rufluxed for 3 h at 0°C to get a crude product. This was added dropwise to a solution of dichloromethane (150 ml) and I₂ for an overnight reaction to give 3-iodo-7-methoxy-chromen-4-one with a 70% yield. Another 100 ml round-bottom flask fitted with mechanical stirrer was loaded with a mixture of 75 ml DMF and 5 ml water, then 3-iodo-7-methyloxy-4 H-chromone (3.0 g, 0.010 mol), methyl acrylate (1.2 g, 0.015 mol), Pd(Ph₃P)₂Cl₂ (0.07 g, 0.1 mmol), CuI (0.19 g, 10 mmol), and K₂CO₃ (1.38 g, 0.01 mol) were added successively. The mixture was heated to 70°C and stirred for 4 h. Then the mixture was filtered. The filtrate was poured into 100 ml of ice-water and then extracted with EtOAc. The extract was washed with saturated NaCl solution, dried over anhydrous MgSO₄, and concentrated to a volume of approximately 30 ml. The target compound 3-(7-methoxy-4-oxo-4H-chromen-3-yl)acrylic acid methyl ester was collected after the concentrated solution was cooled down to 4°C and maintained overnight (2.1 g, 76%). The solution of 3-(7-methoxy-4-oxo-4H-chromen-3-yl)acrylic acid methyl ester (1.04 g, 0.004 mol), 4-chlorophenylamine (0.41 g, 0.0044 mol), and triethylamine (3 drops) in MeOH (45 ml) was stirred under reflux for 8 h. After the mixture was cooled to room temperature and the solvent removed, the crude product was purified by chromatography over silica gel to give 1-(4-chlorophenyl)-5-(2-hydroxy-4-methoxy-benzoyl)-1H-pyridin-2-one with a yield of 72%. Then a solution of NaOH (0.004 mol) in water (5 ml) was added dropwise to a solution of 1-(4-chlorophenyl)-5-(2-hydroxy-4-methoxy-benzoyl)-1H-pyridin-2-one (0.003 mol) in ethanol (50 ml). Reaction at room temperature for 10 min gave the crude compound, which was recrystallized to obtain the title compound, 1-(4-chlorophenyl)-5-(2,4-dihydroxybenzoyl)-1H-pyridin-2-one. The recrystallized product was dissolved in EtOAc (1.5 ml) in an ampoule and PE (1.5 ml) was added dropwise. The ampoule was placed in refrigerator and single crystals were obtained by slow evaporation of the solvent (0.3 g, 35%; m.p. 391 K).

Structure description top

For similar structures, see: Ravinder et al. (2012); Sengupta et al. (2012). For the synthesis, see: Chen et al. (2011); Kim & Hong (2011). For the biological activity of similar structures, see: Kim et al. (2010).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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. Molecular structure with the numbering scheme adopted and ellipsoids drawn at the 30% probability level.
	Fig. 2. A view of the unit-cell contents of title compound. Hydrogen bonds are shown as dashed lines.

1-(3-Chlorophenyl)-5-(2,4-dihydroxybenzoyl)pyridin-2(1H)-one top

Crystal data top

C₁₈H₁₂ClNO₄	F(000) = 352
M_r = 341.74	D_x = 1.435 Mg m⁻³
Triclinic, P1	Melting point: 391 K
a = 6.689 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.009 (4) Å	Cell parameters from 841 reflections
c = 13.257 (6) Å	θ = 2.3–26.8°
α = 87.193 (5)°	µ = 0.26 mm⁻¹
β = 87.719 (5)°	T = 293 K
γ = 82.674 (5)°	Block, yellow
V = 791.0 (6) Å³	0.15 × 0.12 × 0.05 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	2726 independent reflections
Radiation source: fine-focus sealed tube	1929 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
φ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −5→7
T_min = 0.962, T_max = 0.987	k = −9→10
3286 measured reflections	l = −14→15

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.233	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.1737P)²] where P = (F_o² + 2F_c²)/3
2726 reflections	(Δ/σ)_max < 0.001
236 parameters	Δρ_max = 0.36 e Å⁻³
48 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₈H₁₂ClNO₄	γ = 82.674 (5)°
M_r = 341.74	V = 791.0 (6) Å³
Triclinic, P1	Z = 2
a = 6.689 (3) Å	Mo Kα radiation
b = 9.009 (4) Å	µ = 0.26 mm⁻¹
c = 13.257 (6) Å	T = 293 K
α = 87.193 (5)°	0.15 × 0.12 × 0.05 mm
β = 87.719 (5)°

Data collection top

Bruker SMART CCD diffractometer	2726 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1929 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.987	R_int = 0.049
3286 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	48 restraints
wR(F²) = 0.233	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.36 e Å⁻³
2726 reflections	Δρ_min = −0.43 e Å⁻³
236 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	Occ. (<1)
C1	0.5151 (4)	−0.2487 (3)	0.2138 (2)	0.0538 (8)
H1A	0.6295	−0.3083	0.2368	0.065*
C2	0.3295 (4)	−0.3066 (3)	0.2132 (2)	0.0495 (7)
C3	0.1599 (4)	−0.2167 (3)	0.1802 (2)	0.0467 (7)
H3	0.0368	−0.2545	0.1811	0.056*
C4	0.1723 (4)	−0.0708 (3)	0.1460 (2)	0.0437 (6)
C5	0.3569 (4)	−0.0092 (3)	0.1467 (2)	0.0445 (6)
C6	0.5255 (4)	−0.1048 (3)	0.1803 (2)	0.0504 (7)
H6	0.6495	−0.0682	0.1796	0.060*
C7	0.3660 (4)	0.1438 (3)	0.1075 (2)	0.0485 (7)
C8	0.5392 (4)	0.2240 (3)	0.1300 (2)	0.0431 (6)
C9	0.6104 (4)	0.3249 (3)	0.0559 (2)	0.0521 (7)
H9	0.5547	0.3347	−0.0076	0.063*
C10	0.7578 (4)	0.4071 (3)	0.0762 (3)	0.0608 (8)
H10	0.8062	0.4692	0.0253	0.073*
C11	0.8409 (4)	0.4009 (3)	0.1736 (2)	0.0554 (8)
C12	0.6192 (4)	0.2166 (3)	0.2224 (2)	0.0460 (7)
H12	0.5742	0.1514	0.2724	0.055*
C13	0.835 (4)	0.298 (2)	0.348 (2)	0.0602 (8)	0.331 (8)
C14	0.679 (4)	0.326 (2)	0.4232 (19)	0.107 (3)	0.331 (8)
H14	0.5465	0.3577	0.4065	0.128*	0.331 (8)
C15	0.737 (4)	0.302 (2)	0.5263 (17)	0.137 (4)	0.331 (8)
H15	0.6406	0.3212	0.5781	0.164*	0.331 (8)
C16	0.928 (4)	0.254 (3)	0.549 (2)	0.109 (3)	0.331 (8)
H16	0.9665	0.2386	0.6154	0.131*	0.331 (8)
C17	1.065 (4)	0.227 (3)	0.471 (2)	0.0914 (18)	0.331 (8)
C18	1.027 (5)	0.242 (3)	0.364 (3)	0.069 (2)	0.331 (8)
H18	1.1232	0.2171	0.3132	0.083*	0.331 (8)
Cl1	1.3150 (14)	0.1781 (14)	0.4928 (8)	0.1598 (17)	0.331 (8)
C13'	0.8340 (19)	0.2944 (10)	0.3452 (10)	0.0602 (8)	0.669 (8)
C14'	0.7299 (15)	0.3857 (11)	0.4146 (8)	0.107 (3)	0.669 (8)
H14'	0.6124	0.4463	0.3966	0.128*	0.669 (8)
C15'	0.7991 (14)	0.3875 (11)	0.5106 (6)	0.137 (4)	0.669 (8)
H15'	0.7286	0.4493	0.5576	0.164*	0.669 (8)
C16'	0.9725 (17)	0.2980 (12)	0.5372 (8)	0.109 (3)	0.669 (8)
H16'	1.0194	0.2993	0.6022	0.131*	0.669 (8)
C17'	1.077 (2)	0.2068 (13)	0.4678 (10)	0.0914 (18)	0.669 (8)
C18'	1.007 (2)	0.2050 (12)	0.3718 (11)	0.069 (2)	0.669 (8)
H18'	1.0780	0.1432	0.3247	0.083*	0.669 (8)
Cl1'	1.2968 (6)	0.0926 (8)	0.5029 (3)	0.1598 (17)	0.669 (8)
N1	0.7644 (3)	0.3024 (2)	0.24405 (18)	0.0477 (6)
O1	0.3277 (3)	−0.4514 (2)	0.24453 (18)	0.0642 (7)
O2	0.0021 (3)	0.0106 (2)	0.11379 (17)	0.0591 (6)
O3	0.2307 (3)	0.2123 (2)	0.05679 (18)	0.0686 (7)
O4	0.9690 (3)	0.4788 (2)	0.1992 (2)	0.0816 (8)
H2	0.044 (5)	0.096 (4)	0.086 (3)	0.077 (10)*
H1	0.214 (7)	−0.478 (5)	0.227 (3)	0.109 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0483 (14)	0.0462 (14)	0.070 (2)	−0.0105 (11)	−0.0145 (13)	−0.0106 (13)
C2	0.0561 (16)	0.0472 (14)	0.0490 (18)	−0.0157 (12)	−0.0057 (12)	−0.0132 (11)
C3	0.0451 (14)	0.0543 (15)	0.0458 (17)	−0.0217 (11)	−0.0010 (11)	−0.0129 (11)
C4	0.0410 (13)	0.0532 (14)	0.0398 (16)	−0.0115 (11)	−0.0027 (10)	−0.0150 (11)
C5	0.0444 (14)	0.0506 (14)	0.0420 (16)	−0.0149 (11)	−0.0030 (10)	−0.0123 (11)
C6	0.0419 (13)	0.0519 (15)	0.061 (2)	−0.0145 (11)	−0.0059 (12)	−0.0161 (12)
C7	0.0430 (14)	0.0538 (15)	0.0516 (18)	−0.0132 (11)	−0.0041 (12)	−0.0112 (12)
C8	0.0462 (13)	0.0413 (12)	0.0442 (17)	−0.0117 (10)	−0.0031 (11)	−0.0079 (10)
C9	0.0550 (15)	0.0587 (15)	0.0453 (18)	−0.0167 (12)	−0.0046 (12)	−0.0019 (12)
C10	0.0614 (17)	0.0601 (17)	0.064 (2)	−0.0251 (14)	−0.0006 (14)	0.0066 (14)
C11	0.0520 (15)	0.0448 (14)	0.073 (2)	−0.0189 (12)	−0.0066 (13)	−0.0067 (13)
C12	0.0526 (14)	0.0428 (13)	0.0454 (18)	−0.0160 (11)	−0.0004 (12)	−0.0056 (11)
C13	0.0676 (18)	0.0643 (18)	0.052 (2)	−0.0113 (14)	−0.0134 (14)	−0.0153 (14)
C14	0.121 (7)	0.130 (8)	0.061 (4)	0.033 (6)	−0.024 (4)	−0.036 (5)
C15	0.172 (8)	0.167 (10)	0.062 (5)	0.032 (8)	−0.024 (5)	−0.051 (6)
C16	0.118 (7)	0.148 (8)	0.065 (4)	−0.024 (5)	−0.029 (4)	−0.012 (5)
C17	0.079 (3)	0.124 (4)	0.072 (3)	−0.009 (3)	−0.026 (2)	0.000 (3)
C18	0.066 (3)	0.077 (7)	0.065 (3)	−0.012 (4)	−0.009 (2)	−0.004 (4)
Cl1	0.1116 (14)	0.220 (5)	0.1318 (18)	0.034 (3)	−0.0528 (12)	0.048 (3)
C13'	0.0676 (18)	0.0643 (18)	0.052 (2)	−0.0113 (14)	−0.0134 (14)	−0.0153 (14)
C14'	0.121 (7)	0.130 (8)	0.061 (4)	0.033 (6)	−0.024 (4)	−0.036 (5)
C15'	0.172 (8)	0.167 (10)	0.062 (5)	0.032 (8)	−0.024 (5)	−0.051 (6)
C16'	0.118 (7)	0.148 (8)	0.065 (4)	−0.024 (5)	−0.029 (4)	−0.012 (5)
C17'	0.079 (3)	0.124 (4)	0.072 (3)	−0.009 (3)	−0.026 (2)	0.000 (3)
C18'	0.066 (3)	0.077 (7)	0.065 (3)	−0.012 (4)	−0.009 (2)	−0.004 (4)
Cl1'	0.1116 (14)	0.220 (5)	0.1318 (18)	0.034 (3)	−0.0528 (12)	0.048 (3)
N1	0.0537 (12)	0.0454 (11)	0.0477 (15)	−0.0153 (9)	−0.0103 (10)	−0.0097 (10)
O1	0.0658 (13)	0.0476 (11)	0.0836 (17)	−0.0193 (9)	−0.0186 (11)	−0.0013 (10)
O2	0.0421 (10)	0.0625 (12)	0.0751 (16)	−0.0144 (9)	−0.0131 (9)	0.0011 (10)
O3	0.0598 (13)	0.0624 (12)	0.0871 (18)	−0.0197 (10)	−0.0250 (11)	0.0100 (11)
O4	0.0729 (14)	0.0669 (14)	0.114 (2)	−0.0362 (11)	−0.0279 (13)	−0.0020 (13)

Geometric parameters (Å, º) top

C1—C6	1.359 (4)	C13—C14	1.42 (3)
C1—C2	1.407 (4)	C13—N1	1.47 (3)
C1—H1A	0.9300	C14—C15	1.43 (3)
C2—O1	1.350 (3)	C14—H14	0.9300
C2—C3	1.380 (4)	C15—C16	1.34 (3)
C3—C4	1.381 (4)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.36 (3)
C4—O2	1.346 (3)	C16—H16	0.9300
C4—C5	1.418 (3)	C17—C18	1.45 (3)
C5—C6	1.402 (4)	C17—Cl1	1.71 (3)
C5—C7	1.457 (4)	C18—H18	0.9300
C6—H6	0.9300	C13'—C18'	1.373 (8)
C7—O3	1.232 (3)	C13'—C14'	1.373 (8)
C7—C8	1.489 (3)	C13'—N1	1.432 (13)
C8—C12	1.352 (4)	C14'—C15'	1.373 (8)
C8—C9	1.415 (4)	C14'—H14'	0.9300
C9—C10	1.349 (4)	C15'—C16'	1.373 (8)
C9—H9	0.9300	C15'—H15'	0.9300
C10—C11	1.422 (4)	C16'—C17'	1.373 (8)
C10—H10	0.9300	C16'—H16'	0.9300
C11—O4	1.242 (3)	C17'—C18'	1.373 (8)
C11—N1	1.385 (4)	C17'—Cl1'	1.750 (14)
C12—N1	1.363 (3)	C18'—H18'	0.9300
C12—H12	0.9300	O1—H1	0.87 (5)
C13—C18	1.34 (2)	O2—H2	0.91 (4)

C6—C1—C2	119.3 (3)	C13—C14—H14	121.6
C6—C1—H1A	120.3	C15—C14—H14	121.6
C2—C1—H1A	120.3	C16—C15—C14	120.6 (18)
O1—C2—C3	122.9 (2)	C16—C15—H15	119.7
O1—C2—C1	117.2 (3)	C14—C15—H15	119.7
C3—C2—C1	119.9 (2)	C15—C16—C17	118.1 (16)
C2—C3—C4	120.3 (2)	C15—C16—H16	120.9
C2—C3—H3	119.8	C17—C16—H16	120.9
C4—C3—H3	119.8	C16—C17—C18	127.1 (13)
O2—C4—C3	117.5 (2)	C16—C17—Cl1	121.1 (18)
O2—C4—C5	121.6 (2)	C18—C17—Cl1	111.6 (18)
C3—C4—C5	120.9 (2)	C13—C18—C17	111.2 (12)
C6—C5—C4	116.9 (2)	C13—C18—H18	124.4
C6—C5—C7	123.5 (2)	C17—C18—H18	124.4
C4—C5—C7	119.5 (2)	C18'—C13'—C14'	120.0
C1—C6—C5	122.6 (2)	C18'—C13'—N1	121.4 (8)
C1—C6—H6	118.7	C14'—C13'—N1	118.4 (7)
C5—C6—H6	118.7	C13'—C14'—C15'	120.0
O3—C7—C5	121.9 (2)	C13'—C14'—H14'	120.0
O3—C7—C8	117.7 (2)	C15'—C14'—H14'	120.0
C5—C7—C8	120.4 (2)	C16'—C15'—C14'	120.0
C12—C8—C9	117.8 (2)	C16'—C15'—H15'	120.0
C12—C8—C7	122.5 (2)	C14'—C15'—H15'	120.0
C9—C8—C7	119.4 (3)	C17'—C16'—C15'	120.0
C10—C9—C8	120.9 (3)	C17'—C16'—H16'	120.0
C10—C9—H9	119.5	C15'—C16'—H16'	120.0
C8—C9—H9	119.5	C16'—C17'—C18'	120.0
C9—C10—C11	121.5 (3)	C16'—C17'—Cl1'	119.5 (8)
C9—C10—H10	119.3	C18'—C17'—Cl1'	120.5 (8)
C11—C10—H10	119.3	C13'—C18'—C17'	120.0
O4—C11—N1	119.4 (3)	C13'—C18'—H18'	120.0
O4—C11—C10	125.1 (3)	C17'—C18'—H18'	120.0
N1—C11—C10	115.5 (2)	C12—N1—C11	122.8 (2)
C8—C12—N1	121.5 (2)	C12—N1—C13'	118.3 (4)
C8—C12—H12	119.3	C11—N1—C13'	118.9 (4)
N1—C12—H12	119.3	C12—N1—C13	119.1 (9)
C18—C13—C14	125.9 (12)	C11—N1—C13	118.0 (9)
C18—C13—N1	118.1 (18)	C2—O1—H1	108 (3)
C14—C13—N1	114.7 (18)	C4—O2—H2	104 (2)
C13—C14—C15	116.8 (16)

C6—C1—C2—O1	178.2 (3)	C15—C16—C17—Cl1	175 (2)
C6—C1—C2—C3	−1.0 (4)	C14—C13—C18—C17	−5.7 (18)
O1—C2—C3—C4	−177.9 (2)	N1—C13—C18—C17	−172.1 (17)
C1—C2—C3—C4	1.2 (4)	C16—C17—C18—C13	4 (2)
C2—C3—C4—O2	179.3 (2)	Cl1—C17—C18—C13	−172.5 (17)
C2—C3—C4—C5	−1.9 (4)	C18'—C13'—C14'—C15'	0.0
O2—C4—C5—C6	−179.0 (2)	N1—C13'—C14'—C15'	−176.2 (8)
C3—C4—C5—C6	2.2 (4)	C13'—C14'—C15'—C16'	0.0
O2—C4—C5—C7	−2.9 (4)	C14'—C15'—C16'—C17'	0.0
C3—C4—C5—C7	178.4 (2)	C15'—C16'—C17'—C18'	0.0
C2—C1—C6—C5	1.4 (5)	C15'—C16'—C17'—Cl1'	−179.7 (7)
C4—C5—C6—C1	−2.0 (4)	C14'—C13'—C18'—C17'	0.0
C7—C5—C6—C1	−178.0 (3)	N1—C13'—C18'—C17'	176.0 (8)
C6—C5—C7—O3	162.1 (3)	C16'—C17'—C18'—C13'	0.0
C4—C5—C7—O3	−13.8 (4)	Cl1'—C17'—C18'—C13'	179.7 (7)
C6—C5—C7—C8	−19.3 (4)	C8—C12—N1—C11	−0.6 (4)
C4—C5—C7—C8	164.8 (2)	C8—C12—N1—C13'	176.6 (6)
O3—C7—C8—C12	136.6 (3)	C8—C12—N1—C13	175.5 (12)
C5—C7—C8—C12	−42.0 (4)	O4—C11—N1—C12	178.0 (2)
O3—C7—C8—C9	−36.4 (4)	C10—C11—N1—C12	−0.1 (4)
C5—C7—C8—C9	145.0 (3)	O4—C11—N1—C13'	0.7 (6)
C12—C8—C9—C10	2.1 (4)	C10—C11—N1—C13'	−177.3 (6)
C7—C8—C9—C10	175.4 (2)	O4—C11—N1—C13	1.8 (12)
C8—C9—C10—C11	−2.9 (4)	C10—C11—N1—C13	−176.2 (12)
C9—C10—C11—O4	−176.1 (3)	C18'—C13'—N1—C12	97.6 (6)
C9—C10—C11—N1	1.8 (4)	C14'—C13'—N1—C12	−86.3 (6)
C9—C8—C12—N1	−0.4 (4)	C18'—C13'—N1—C11	−85.0 (6)
C7—C8—C12—N1	−173.4 (2)	C14'—C13'—N1—C11	91.0 (6)
C18—C13—C14—C15	4.8 (13)	C18—C13—N1—C12	114.9 (13)
N1—C13—C14—C15	171.6 (15)	C14—C13—N1—C12	−53.0 (14)
C13—C14—C15—C16	−1.3 (16)	C18—C13—N1—C11	−68.8 (15)
C14—C15—C16—C17	0 (3)	C14—C13—N1—C11	123.3 (10)
C15—C16—C17—C18	−1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.91 (4)	1.75 (4)	2.587 (3)	152 (3)
O1—H1···O4ⁱ	0.87 (5)	1.79 (5)	2.655 (3)	175 (4)
C3—H3···O4ⁱ	0.93	2.50	3.165 (3)	129
C15—H15···O1ⁱⁱ	0.93	2.71	3.37 (2)	129

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂ClNO₄
M_r	341.74
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.689 (3), 9.009 (4), 13.257 (6)
α, β, γ (°)	87.193 (5), 87.719 (5), 82.674 (5)
V (Å³)	791.0 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.15 × 0.12 × 0.05

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.962, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	3286, 2726, 1929
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.233, 1.00
No. of reflections	2726
No. of parameters	236
No. of restraints	48
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.43

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
O2—H2···O3	0.91 (4)	1.75 (4)	2.587 (3)	152 (3)
O1—H1···O4ⁱ	0.87 (5)	1.79 (5)	2.655 (3)	175 (4)
C3—H3···O4ⁱ	0.93	2.50	3.165 (3)	128.7
C15—H15···O1ⁱⁱ	0.93	2.71	3.37 (2)	129.2

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

Acknowledgements

We are grateful to Attending Physician Tongqin Hao (The First Affiliated Hospital of Xinxiang Medical University, Henan, China) for the assistance with the antitumor assay.

References

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