catena-Poly[[(liriodenine-κ2N,O)lead(II)]-di-μ-chlorido]

Qin, Y.-T.; Tao, L.; He, T.-J.; Liu, Y.-C.; Chen, Z.-F.

doi:10.1107/S1600536809051381

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m29

doi:10.1107/S1600536809051381

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catena-Poly[[(liriodenine-κ²N,O)lead(II)]-di-μ-chlorido]

Yan-Tao Qin,^a Lu Tao,^a Tian-Jing He,^a Yan-Cheng Liu ^a and Zhen-Feng Chen ^a ^*

^aKey Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), School of Chemistry & Chemical Engineering, Guangxi Normal University, Guilin 541004, People's Republic of China
^*Correspondence e-mail: chenzfgxnu@yahoo.com

(Received 1 November 2009; accepted 28 November 2009; online 9 December 2009)

The title compound, [PbCl₂(C₁₇H₉NO₃)]_n, was synthesized by the hydrothermal reaction of PbCl₂ and liriodenine. The lead(II) atom has a distorted octahedral environment made up of the O and N atoms of the liriodenine ligand [Pb—O 2.666 (4) Å, Pb—N 2.587 (5) Å, O—Pb—N 61.78 (14)°] and four bridging chloro ligands, which link the complex molecules into infinite chains along the a axis. Both crystallographically independent chloro-bridges are asymmetric, so that the Pb atom participates in two short [2.6872 (18) and 2.7952 (18) Å] and two noticeably longer Pb—Cl bonds [2.9626 (18) and 3.031 (2) Å].

Related literature

For liriodenine metal complexes, see: Chen et al. (2009 ). For the structure of a similar lead(II) coordination polymer, see: Engelhardt et al. (1987 ).

Experimental

Crystal data

[PbCl₂(C₁₇H₉NO₃)]
M_r = 553.34
Triclinic, $[P \overline 1]$
a = 7.2280 (18) Å
b = 10.332 (3) Å
c = 11.307 (3) Å
α = 104.481 (6)°
β = 100.479 (4)°
γ = 99.686 (4)°
V = 783.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 11.13 mm⁻¹
T = 293 K
0.35 × 0.20 × 0.15 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.077, T_max = 0.188
7685 measured reflections
2847 independent reflections
2545 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.065
S = 1.05
2847 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 1.19 e Å⁻³
Δρ_min = −1.28 e Å⁻³

Data collection: CrystalClear (Rigaku, 1999 ); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2000 ); 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, New_Global_Publ_Block. DOI: 10.1107/S1600536809051381/ya2112sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051381/ya2112Isup2.hkl

checkCIF report

Comment top

Liriodenine, 8H-[1,3]benzodioxolo[6,5,4-de]benzo[g]quinolin-8-one, is an oxo-aporphine alkaloid, which was isolated from the Z. nitidum (TCM) spiders found in China (Chen et al., 2009). With its N and carbonyl O donor atoms, liriodenine can serve as bidentate chelate ligand in metal complex. In our previous work, the synthesis, crystal structures and anticancer activity of platinum(II) and ruthenium(II) complexes of liriodenine were reported (Chen et al., 2009). In order to extend our knowledge on liriodenine coordination chemistry we turned to the main-group metals and report herein the the first structure of lead(II) complex with liriodenine.

As shown in Fig.1, similarly to what was observed in the structure of catena-[cis-bis(µ₂-chloro)-(3-methylpyridine-N)]lead(II) (Engelhardt et al., 1987), the Pb1 atom in the title compound is six-coordinated by the O1 and N1 atoms of the liriodenine ligand [Pb1—O1 2.666 (4) Å, Pb1—N1 2.587 (5) Å] and four µ₂-chloro-atoms which link the complex molecules into infinite chains running along the a axis. The chloro-bridges show noticeable asymmetry with the Pb1—Cl1 [2.7952 (18) Å] and Pb1—Cl2 [2.6872 (18) Å] bonds being significantly shorter than Pb1—Cl1ⁱⁱ [3.031 (2) Å], and Pb1—Cl2ⁱ [2.9626 (18) Å] (see Fig. 1). The octahedral coordination of the Pb1 atom shows considerable distortion due to the presence of the chelate ligand [angle O1—Pb1—N1 is equal to 61.78 (14)°] and the asymmetry of the chloro-bridges, e.g. the N1—Pb1—Cl2 and O1—Pb1—Cl2 angles are 84.80 (11)° and 136.98 (11)°, respectively. The overall geometry of the complex compares quite well with that of catena-(cis-bis((µ₂-chloro)-(3-methylpyridine-N)) lead(II) (Engelhardt et al. 1987), and the geometric parameters of liriodenine are close to those reported previously (Chen et al., 2009).

Related literature top

For liriodenine metal complexes, see: Chen et al. (2009). For the structure of similar lead(II) coordination polymer, see: Engelhardt et al. (1987).

Experimental top

PbCl₂ (0.8 mmol, 0.222 g) and liriodenine (0.8 mmol, 0.220 g) were thoroughly mixed in a mortar with a pestle, and placed in a thick-walled Pyrex tube (ca 20 cm long). After addition of EtOH (0.6 ml) and H₂O (0.3 ml), the tube was frozen with liquid nitrogen, evacuated under vacuum and sealed with a torch. The tube was heated at 110°C for 2 days and then slowly cooled down to room temperature; brown-red block crystals were obtained. Yield: 40%.

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2000); 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 of the title compound, showing the atom-labelling scheme; displacement ellipsoids are drawn at the 50% probability level. Symmetry transformations (i): -x + 1, -y + 1, -z + 1; (ii): -x,-y + 1,-z + 1.

catena-Poly[[(liriodenine-κ²N,O)lead(II)]- di-µ-chlorido] top

Crystal data top

[PbCl₂(C₁₇H₉NO₃)]	Z = 2
M_r = 553.34	F(000) = 516
Triclinic, P1	D_x = 2.346 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 7.2280 (18) Å	Cell parameters from 3068 reflections
b = 10.332 (3) Å	θ = 3.1–25.3°
c = 11.307 (3) Å	µ = 11.13 mm⁻¹
α = 104.481 (6)°	T = 293 K
β = 100.479 (4)°	Block, brown-red
γ = 99.686 (4)°	0.35 × 0.20 × 0.15 mm
V = 783.4 (3) Å³

Data collection top

Rigaku Mercury CCD diffractometer	2847 independent reflections
Radiation source: fine-focus sealed tube	2545 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.3°, θ_min = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −12→12
T_min = 0.077, T_max = 0.188	l = −13→11
7685 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0269P)²] where P = (F_o² + 2F_c²)/3
2847 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 1.19 e Å⁻³
0 restraints	Δρ_min = −1.28 e Å⁻³

Crystal data top

[PbCl₂(C₁₇H₉NO₃)]	γ = 99.686 (4)°
M_r = 553.34	V = 783.4 (3) Å³
Triclinic, P1	Z = 2
a = 7.2280 (18) Å	Mo Kα radiation
b = 10.332 (3) Å	µ = 11.13 mm⁻¹
c = 11.307 (3) Å	T = 293 K
α = 104.481 (6)°	0.35 × 0.20 × 0.15 mm
β = 100.479 (4)°

Data collection top

Rigaku Mercury CCD diffractometer	2847 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	2545 reflections with I > 2σ(I)
T_min = 0.077, T_max = 0.188	R_int = 0.040
7685 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 1.05	Δρ_max = 1.19 e Å⁻³
2847 reflections	Δρ_min = −1.28 e Å⁻³
218 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
Pb1	0.19801 (4)	0.42620 (2)	0.40684 (2)	0.03726 (11)
Cl1	−0.1055 (3)	0.29827 (18)	0.4893 (2)	0.0629 (6)
Cl2	0.4274 (3)	0.44005 (18)	0.62730 (15)	0.0502 (5)
O1	0.1822 (7)	0.3210 (4)	0.1636 (4)	0.0497 (12)
O2	0.3150 (8)	−0.4078 (5)	0.0294 (4)	0.0578 (14)
O3	0.2905 (7)	−0.2806 (4)	−0.1103 (4)	0.0480 (12)
N1	0.2587 (7)	0.1823 (5)	0.3329 (4)	0.0326 (12)
C1	0.2820 (9)	0.1075 (7)	0.4135 (6)	0.0398 (16)
H1	0.2900	0.1488	0.4979	0.048*
C2	0.2945 (9)	−0.0270 (7)	0.3773 (6)	0.0395 (15)
H2	0.3066	−0.0751	0.4366	0.047*
C3	0.2895 (8)	−0.0921 (6)	0.2529 (5)	0.0313 (14)
C4	0.2695 (8)	−0.0126 (6)	0.1654 (5)	0.0273 (13)
C5	0.2517 (8)	0.1231 (6)	0.2115 (5)	0.0276 (13)
C6	0.2153 (8)	0.2068 (6)	0.1253 (5)	0.0302 (14)
C7	0.2194 (8)	0.1492 (6)	−0.0059 (5)	0.0303 (14)
C8	0.1938 (9)	0.2315 (6)	−0.0863 (6)	0.0365 (15)
H8	0.1783	0.3203	−0.0549	0.044*
C9	0.1914 (9)	0.1812 (7)	−0.2120 (6)	0.0420 (16)
H9	0.1775	0.2360	−0.2655	0.050*
C10	0.2102 (9)	0.0463 (7)	−0.2573 (6)	0.0447 (17)
H10	0.2059	0.0111	−0.3421	0.054*
C11	0.2351 (9)	−0.0361 (6)	−0.1792 (5)	0.0349 (15)
H11	0.2488	−0.1250	−0.2117	0.042*
C12	0.2399 (7)	0.0135 (6)	−0.0515 (5)	0.0252 (13)
C13	0.2642 (8)	−0.0694 (6)	0.0357 (5)	0.0259 (13)
C14	0.2808 (9)	−0.2026 (6)	0.0034 (6)	0.0360 (15)
C15	0.2995 (9)	−0.2795 (6)	0.0903 (6)	0.0374 (15)
C16	0.3033 (9)	−0.2300 (6)	0.2118 (6)	0.0401 (16)
H16	0.3144	−0.2837	0.2666	0.048*
C17	0.2998 (14)	−0.4135 (7)	−0.0990 (7)	0.066 (2)
H17A	0.1845	−0.4802	−0.1511	0.079*
H17B	0.4111	−0.4405	−0.1261	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.04943 (18)	0.03102 (16)	0.03286 (16)	0.01243 (12)	0.01518 (11)	0.00575 (10)
Cl1	0.0760 (14)	0.0351 (10)	0.0866 (14)	0.0132 (9)	0.0457 (12)	0.0144 (9)
Cl2	0.0624 (12)	0.0544 (11)	0.0345 (9)	0.0071 (9)	0.0160 (8)	0.0146 (8)
O1	0.086 (4)	0.034 (3)	0.032 (3)	0.023 (3)	0.013 (2)	0.008 (2)
O2	0.101 (4)	0.032 (3)	0.048 (3)	0.027 (3)	0.027 (3)	0.011 (2)
O3	0.080 (4)	0.032 (3)	0.035 (3)	0.022 (2)	0.020 (2)	0.005 (2)
N1	0.040 (3)	0.033 (3)	0.024 (3)	0.011 (2)	0.006 (2)	0.008 (2)
C1	0.053 (4)	0.044 (4)	0.024 (3)	0.016 (3)	0.007 (3)	0.009 (3)
C2	0.052 (4)	0.038 (4)	0.034 (4)	0.017 (3)	0.011 (3)	0.015 (3)
C3	0.033 (3)	0.032 (4)	0.030 (3)	0.009 (3)	0.006 (3)	0.012 (3)
C4	0.022 (3)	0.028 (3)	0.032 (3)	0.006 (3)	0.009 (2)	0.008 (3)
C5	0.031 (3)	0.023 (3)	0.027 (3)	0.006 (3)	0.007 (2)	0.004 (2)
C6	0.032 (3)	0.023 (3)	0.029 (3)	0.002 (3)	0.004 (3)	0.002 (3)
C7	0.028 (3)	0.031 (3)	0.030 (3)	0.004 (3)	0.008 (3)	0.006 (3)
C8	0.047 (4)	0.030 (4)	0.031 (3)	0.003 (3)	0.009 (3)	0.010 (3)
C9	0.055 (4)	0.037 (4)	0.040 (4)	0.010 (3)	0.014 (3)	0.019 (3)
C10	0.049 (4)	0.053 (5)	0.028 (3)	0.006 (4)	0.014 (3)	0.006 (3)
C11	0.039 (4)	0.034 (4)	0.031 (3)	0.006 (3)	0.012 (3)	0.007 (3)
C12	0.023 (3)	0.024 (3)	0.028 (3)	0.004 (2)	0.008 (2)	0.004 (2)
C13	0.025 (3)	0.023 (3)	0.030 (3)	0.009 (2)	0.010 (2)	0.003 (2)
C14	0.043 (4)	0.033 (4)	0.033 (4)	0.011 (3)	0.017 (3)	0.003 (3)
C15	0.046 (4)	0.024 (3)	0.048 (4)	0.014 (3)	0.018 (3)	0.012 (3)
C16	0.054 (4)	0.031 (4)	0.044 (4)	0.013 (3)	0.018 (3)	0.018 (3)
C17	0.116 (7)	0.034 (4)	0.046 (5)	0.021 (4)	0.024 (5)	0.003 (3)

Geometric parameters (Å, º) top

Pb1—N1	2.587 (5)	C4—C5	1.405 (8)
Pb1—O1	2.666 (4)	C4—C13	1.428 (7)
Pb1—Cl2	2.6872 (18)	C5—C6	1.474 (8)
Pb1—Cl1	2.7952 (18)	C6—C7	1.462 (8)
Pb1—Cl2ⁱ	2.9626 (18)	C7—C8	1.401 (8)
Pb1—Cl1ⁱⁱ	3.031 (2)	C7—C12	1.411 (8)
Cl1—Pb1ⁱⁱ	3.031 (2)	C8—C9	1.382 (8)
Cl2—Pb1ⁱ	2.9626 (18)	C8—H8	0.9300
O1—C6	1.230 (7)	C9—C10	1.399 (9)
O2—C15	1.366 (7)	C9—H9	0.9300
O2—C17	1.422 (8)	C10—C11	1.380 (9)
O3—C14	1.356 (7)	C10—H10	0.9300
O3—C17	1.422 (8)	C11—C12	1.397 (8)
N1—C1	1.340 (7)	C11—H11	0.9300
N1—C5	1.344 (7)	C12—C13	1.465 (8)
C1—C2	1.370 (9)	C13—C14	1.365 (8)
C1—H1	0.9300	C14—C15	1.412 (8)
C2—C3	1.390 (8)	C15—C16	1.334 (8)
C2—H2	0.9300	C16—H16	0.9300
C3—C16	1.411 (8)	C17—H17A	0.9700
C3—C4	1.438 (8)	C17—H17B	0.9700

N1—Pb1—O1	61.78 (14)	O1—C6—C5	120.5 (5)
N1—Pb1—Cl2	84.80 (11)	C7—C6—C5	117.8 (5)
O1—Pb1—Cl2	136.98 (11)	C8—C7—C12	121.0 (5)
N1—Pb1—Cl1	84.76 (11)	C8—C7—C6	117.6 (5)
O1—Pb1—Cl1	114.05 (11)	C12—C7—C6	121.3 (5)
Cl2—Pb1—Cl1	86.77 (6)	C9—C8—C7	120.2 (6)
N1—Pb1—Cl2ⁱ	93.28 (11)	C9—C8—H8	119.9
O1—Pb1—Cl2ⁱ	75.61 (11)	C7—C8—H8	119.9
Cl2—Pb1—Cl2ⁱ	80.49 (5)	C8—C9—C10	118.7 (6)
Cl1—Pb1—Cl2ⁱ	167.23 (6)	C8—C9—H9	120.6
N1—Pb1—Cl1ⁱⁱ	174.35 (11)	C10—C9—H9	120.6
O1—Pb1—Cl1ⁱⁱ	122.56 (10)	C11—C10—C9	121.7 (6)
Cl2—Pb1—Cl1ⁱⁱ	92.96 (6)	C11—C10—H10	119.2
Cl1—Pb1—Cl1ⁱⁱ	89.95 (5)	C9—C10—H10	119.2
Cl2ⁱ—Pb1—Cl1ⁱⁱ	91.45 (5)	C10—C11—C12	120.4 (6)
Pb1—Cl1—Pb1ⁱⁱ	90.05 (5)	C10—C11—H11	119.8
Pb1—Cl2—Pb1ⁱ	99.51 (5)	C12—C11—H11	119.8
C6—O1—Pb1	120.2 (4)	C11—C12—C7	118.0 (5)
C15—O2—C17	107.0 (5)	C11—C12—C13	122.9 (5)
C14—O3—C17	107.2 (5)	C7—C12—C13	119.1 (5)
C1—N1—C5	118.2 (5)	C14—C13—C4	114.7 (5)
C1—N1—Pb1	120.4 (4)	C14—C13—C12	125.1 (5)
C5—N1—Pb1	121.2 (4)	C4—C13—C12	120.3 (5)
N1—C1—C2	123.1 (5)	O3—C14—C13	127.8 (6)
N1—C1—H1	118.5	O3—C14—C15	109.0 (5)
C2—C1—H1	118.5	C13—C14—C15	123.1 (5)
C1—C2—C3	120.7 (6)	C16—C15—O2	127.3 (6)
C1—C2—H2	119.7	C16—C15—C14	123.8 (6)
C3—C2—H2	119.7	O2—C15—C14	108.8 (5)
C2—C3—C16	122.5 (5)	C15—C16—C3	116.5 (6)
C2—C3—C4	117.1 (5)	C15—C16—H16	121.8
C16—C3—C4	120.4 (5)	C3—C16—H16	121.8
C5—C4—C13	120.8 (5)	O2—C17—O3	107.6 (5)
C5—C4—C3	117.6 (5)	O2—C17—H17A	110.2
C13—C4—C3	121.6 (5)	O3—C17—H17A	110.2
N1—C5—C4	123.2 (5)	O2—C17—H17B	110.2
N1—C5—C6	116.2 (5)	O3—C17—H17B	110.2
C4—C5—C6	120.5 (5)	H17A—C17—H17B	108.5
O1—C6—C7	121.7 (5)

N1—Pb1—Cl1—Pb1ⁱⁱ	178.04 (11)	N1—C5—C6—C7	176.0 (5)
O1—Pb1—Cl1—Pb1ⁱⁱ	−126.08 (11)	C4—C5—C6—C7	−6.5 (8)
Cl2—Pb1—Cl1—Pb1ⁱⁱ	92.96 (6)	O1—C6—C7—C8	3.1 (9)
Cl2ⁱ—Pb1—Cl1—Pb1ⁱⁱ	96.4 (2)	C5—C6—C7—C8	−177.1 (5)
Cl1ⁱⁱ—Pb1—Cl1—Pb1ⁱⁱ	0.0	O1—C6—C7—C12	−174.1 (5)
N1—Pb1—Cl2—Pb1ⁱ	94.22 (11)	C5—C6—C7—C12	5.7 (8)
O1—Pb1—Cl2—Pb1ⁱ	56.71 (16)	C12—C7—C8—C9	−1.1 (9)
Cl1—Pb1—Cl2—Pb1ⁱ	179.24 (6)	C6—C7—C8—C9	−178.3 (6)
Cl2ⁱ—Pb1—Cl2—Pb1ⁱ	0.0	C7—C8—C9—C10	1.6 (9)
Cl1ⁱⁱ—Pb1—Cl2—Pb1ⁱ	−90.98 (6)	C8—C9—C10—C11	−1.4 (10)
N1—Pb1—O1—C6	−1.9 (4)	C9—C10—C11—C12	0.8 (10)
Cl2—Pb1—O1—C6	41.5 (5)	C10—C11—C12—C7	−0.3 (8)
Cl1—Pb1—O1—C6	−71.3 (5)	C10—C11—C12—C13	179.4 (6)
Cl2ⁱ—Pb1—O1—C6	99.9 (5)	C8—C7—C12—C11	0.4 (8)
Cl1ⁱⁱ—Pb1—O1—C6	−177.8 (4)	C6—C7—C12—C11	177.6 (5)
O1—Pb1—N1—C1	−174.8 (5)	C8—C7—C12—C13	−179.3 (5)
Cl2—Pb1—N1—C1	33.3 (4)	C6—C7—C12—C13	−2.2 (8)
Cl1—Pb1—N1—C1	−53.9 (4)	C5—C4—C13—C14	−179.2 (5)
Cl2ⁱ—Pb1—N1—C1	113.5 (4)	C3—C4—C13—C14	−0.5 (8)
O1—Pb1—N1—C5	−0.4 (4)	C5—C4—C13—C12	0.0 (8)
Cl2—Pb1—N1—C5	−152.2 (4)	C3—C4—C13—C12	178.8 (5)
Cl1—Pb1—N1—C5	120.5 (4)	C11—C12—C13—C14	−1.3 (9)
Cl2ⁱ—Pb1—N1—C5	−72.1 (4)	C7—C12—C13—C14	178.4 (5)
C5—N1—C1—C2	−1.5 (9)	C11—C12—C13—C4	179.5 (5)
Pb1—N1—C1—C2	173.0 (5)	C7—C12—C13—C4	−0.8 (8)
N1—C1—C2—C3	2.0 (10)	C17—O3—C14—C13	−177.9 (7)
C1—C2—C3—C16	179.6 (6)	C17—O3—C14—C15	4.7 (7)
C1—C2—C3—C4	−0.4 (9)	C4—C13—C14—O3	−176.3 (6)
C2—C3—C4—C5	−1.6 (8)	C12—C13—C14—O3	4.5 (10)
C16—C3—C4—C5	178.4 (5)	C4—C13—C14—C15	0.8 (9)
C2—C3—C4—C13	179.6 (5)	C12—C13—C14—C15	−178.5 (6)
C16—C3—C4—C13	−0.4 (8)	C17—O2—C15—C16	179.0 (7)
C1—N1—C5—C4	−0.7 (8)	C17—O2—C15—C14	−1.8 (8)
Pb1—N1—C5—C4	−175.2 (4)	O3—C14—C15—C16	177.3 (6)
C1—N1—C5—C6	176.8 (5)	C13—C14—C15—C16	−0.2 (10)
Pb1—N1—C5—C6	2.2 (7)	O3—C14—C15—O2	−1.8 (7)
C13—C4—C5—N1	−179.0 (5)	C13—C14—C15—O2	−179.4 (6)
C3—C4—C5—N1	2.2 (8)	O2—C15—C16—C3	178.3 (6)
C13—C4—C5—C6	3.7 (8)	C14—C15—C16—C3	−0.7 (10)
C3—C4—C5—C6	−175.1 (5)	C2—C3—C16—C15	−179.0 (6)
Pb1—O1—C6—C7	−176.2 (4)	C4—C3—C16—C15	0.9 (9)
Pb1—O1—C6—C5	3.9 (7)	C15—O2—C17—O3	4.7 (8)
N1—C5—C6—O1	−4.1 (8)	C14—O3—C17—O2	−5.8 (8)
C4—C5—C6—O1	173.4 (5)

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

Experimental details

Crystal data
Chemical formula	[PbCl₂(C₁₇H₉NO₃)]
M_r	553.34
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.2280 (18), 10.332 (3), 11.307 (3)
α, β, γ (°)	104.481 (6), 100.479 (4), 99.686 (4)
V (Å³)	783.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	11.13
Crystal size (mm)	0.35 × 0.20 × 0.15

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.077, 0.188
No. of measured, independent and observed [I > 2σ(I)] reflections	7685, 2847, 2545
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.065, 1.05
No. of reflections	2847
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.19, −1.28

Computer programs: CrystalClear (Rigaku, 1999), CrystalStructure (Rigaku/MSC & Rigaku, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank the National Natural Science Foundation of China (No. 20861002), the National Basic Research Program of China (2009CB526503), the Natural Science Foundation of Guangxi of China (No. 0991003,0991012Z) and the Open Foundation of the Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China) for financial support.

References

Chen, Z.-F., Liu, Y.-C., Liu, L.-M., Wang, H.-S., Qin, S.-H., Wang, B.-L., Bian, H.-D., Yang, B., Fun, H.-G., Liu, H.-G., Liang, H. & Orvig, C. (2009). J. Chem. Soc. Dalton Trans. pp. 262–272. CrossRef CAS Google Scholar
Engelhardt, L. M., Patrick, J. M., Whitaker, C. R. & White, A. H. (1987). Aust. J. Chem. 40, 2107–2114. CrossRef CAS Google Scholar
Jacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA. Google Scholar
Rigaku (1999). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC & Rigaku (2000). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Coporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar