catena-Poly[[(μ-3-hy­droxy­benzoato-κ³O¹,O^1′:O³)(μ-3-hy­droxy­benzoato-κ³O¹,O^1′:O¹)(isonicotinamide-κN¹)­lead(II)] monohydrate]

In the crystal of the title polymeric compound, {[Pb(C₇H₅O₃)₂(C₆H₆N₂O)]·H₂O}_n, the Pb^II ion is chelated by two carboxyl­ate groups of 3-hy­droxy­benzoate (HB) anions, and coordinated by one isonicotinamide mol­ecule; a carboxyl­ate O atom and a hy­droxy O atom from adjacent HB anions bridge the Pb^II ion to form polymeric chains along [100], in which the Pb^II ion is in an irregular seven-coordination geometry. The carboxyl­ate groups of the HB ions are slightly twisted away from the attached benzene rings by 2.84 (15) and 4.8 (2)°. The planes of the two benzene rings of the HB ions are oriented with respect to each other at a dihedral angle of 84.41 (8)°. In the crystal, adjacent polymeric chains inter­act via O—H...O, N—H...O and weak C—H...O hydrogen bonds. The solvent water mol­ecule links with the polymeric chains via O—H...O hydrogen bonding. π–π stacking between the benzene and pyridine rings and between the benzene rings [centroid–centroid distances = 3.731 (2) and 3.353 (2) Å] are present in the crystal.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.017
• wR factor = 0.050
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT919_ALERT_3_B Reflection # Likely Affected by the Beamstop ...          2
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW .gt. 10 Outliers .          3

Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         12
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         67

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          6
PLAT004_ALERT_5_G Info: Polymeric Structure Found with Dimension .          1
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Pb1    --  O3_a    ..        7.0 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Pb1    --  O5_c    ..        5.1 su
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

   0 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

S1. Comment

As a part of our ongoing investigation on transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

In the crystal structure of the polymeric title compound, (I), the Pb^II ion is chelated by two carboxyl groups of 3-hydroxybenzoate (HB) anions, and coordinated by one isonicotinamide (INA) molecule (Fig. 1); a carboxyl-O atom and a hydroxyl-O atom from adjacent HB anions bridge the Pb^II ion to form the polymeric complex, in which the Pb^II ion is in an irregular seven-coordination geometry (Fig. 2). The two HB ions act as bidentate ligands, while the INA is monodentate ligand (Fig. 1).

The average Pb-O bond length (Table 1) is 2.539 (2) Å, and the Pb atom is displaced out of the least-squares planes of the carboxylate groups (O1/C1/O2) and (O4/C8/O5) by -0.0641 (1) and -0.0110 (1) Å, respectively. In (I), the O1-Pb1-O2 and O4-Pb1-O5 angles are 51.00 (6) and 50.94 (6) °, respectively. The corresponding O-M-O (where M is a metal) angles are 51.10 (15)° and 51.95 (16)° in {[Pb(PEB)₂(NA)].H₂O}_n (Hökelek et al., 2011), 51.09 (6)° and 51.71 (5)° in [Pb(PMB)₂(NA)]_n (Hökelek, Dal et al., 2010), 55.96 (4)° and 53.78 (4)° in [Cd₂(DMAB)₄(NA)₂(H₂O)₂] (Hökelek, Süzen et al., 2010), 52.91 (4)° and 53.96 (4)° in [Cd(FB)₂(INA)₂(H₂O)].H₂O (Hökelek, Yılmaz et al., 2009), 60.70 (4)° in [Co(DMAB)₂(INA)(H₂O)₂] (Hökelek, Dal et al., 2009a), 58.45 (9)° in [Mn(DMAB)₂(INA)(H₂O)₂] (Hökelek, Dal et al., 2009b), 60.03 (6)° in [Zn(MAB)₂(INA)₂].H₂O (Hökelek, Dal et al., 2009c), 58.3 (3)° in [Zn₂(DENA)₂(HB)₄].2H₂O (Hökelek & 'Necefoğlu, 1996) [where NA, INA, DENA, HB, FB, MAB, PMB, PEB and DMAB are nicotinamide, isonicotinamide, N,N-diethylnicotinamide, 4-hydroxybenzoate, 4-formylbenzoate, 4-methylaminobenzoate, 4-methylbenzoate, 4-ethylbenzoate and 4-dimethylaminobenzoate, respectively] and 55.2 (1)° in [Cu(Asp)₂(py)₂] (where Asp is acetylsalicylate and py is pyridine) (Greenaway et al., 1984).

The dihedral angles between the planar carboxylate groups and the adjacent benzene rings A (C2-C7) and B (C9-C14) are 2.84 (15) and 4.8 (2) °, respectively, while those between rings A, B, C (N1/C15-C19), D (Pb1/O1/O2/C1) and E (Pb1/O4/O5/C8) are A/B = 84.41 (8), A/C = 87.69 (7), B/C = 10.23 (9) and D/E = 80.12 (9)°.

In the crystal, adjacent polymeric chains interact via O—H···O, N—H···O and weak C—H···O hydrogen bonds; and the lattice water molecule links with the polymeric chains via O—H···O hydrogen bonding (Table 2), in which they may be effective in the stabilization of the structure. π···π Contacts between the benzene and pyridine rings and between the benzene rings, Cg3—Cg2ⁱ and Cg1—Cg1ⁱⁱ [symmetry codes: (i) 1 - x, 2 - y, -z, (ii) 1 - x, 1 - y, 1 - z, where Cg1, Cg2 and Cg3 are the centroids of the rings A (C2-C7), B (C9-C14) and C (N1/C15-C19), respectively] may further stabilize the structure, with centroid-centroid distances of 3.731 (2) and 3.353 (2) Å, respectively.

Related literature

For niacin, see: Krishnamachari (1974). For N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Greenaway et al. (1984); Hökelek & Necefouglu (1996); Hökelek, Yılmaz et al. (2009); Hökelek, Dal et al. (2009a,b,c, 2010); Hökelek, Süzen et al. (2010); Hökelek et al. (2011).

S2. Experimental

The title compound was prepared by the reaction of Pb(NO₃)₂ (1.656 g, 5 mmol) in H₂O (100 ml) and INA (1.220 g, 10 mmol) in H₂O (50 ml) with sodium 3-hydroxybenzoate (1.601 g, 10 mmol) in H₂O (100 ml). The mixture was filtered and set aside to crystallize at ambient temperature for two weeks, giving yellow single crystals.

S3. Refinement

Atoms H81 and H82 (for H₂O), H21 and H22 (for NH₂) and H31 and H61 (for OH) were located in a difference Fourier map and were refined isotropically. The C-bound H-atoms were positioned geometrically with C—H = 0.93 Å and constrained to ride on their parent atoms, with U_iso(H) = 1.2U_eq(C).

Computing details

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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures

	Fig. 1. The asymmetric unit of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The polymeric structure.

catena-Poly[[(µ-3-hydroxybenzoato- κ³O¹,O^1':O³)(µ-3-hydroxybenzoato- κ³O¹,O^1':O¹)(isonicotinamide- κN¹)lead(II)] monohydrate]

Crystal data

[Pb(C7H5O3)2(C6H6N2O)]·H2O	Z = 2
Mr = 621.56	F(000) = 596
Triclinic, P1	Dx = 2.149 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3626 (2) Å	Cell parameters from 9959 reflections
b = 12.1382 (3) Å	θ = 2.9–28.5°
c = 12.1789 (3) Å	µ = 8.84 mm^−1
α = 67.165 (2)°	T = 100 K
β = 74.192 (3)°	Block, yellow
γ = 88.921 (3)°	0.26 × 0.14 × 0.13 mm
V = 960.53 (5) Å^3

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer	4783 independent reflections
Radiation source: fine-focus sealed tube	4652 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ϕ and ω scans	θmax = 28.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.395, Tmax = 0.603	k = −16→16
17040 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.050	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0228P)^2 + 0.6812P] where P = (Fo^2 + 2Fc^2)/3
4783 reflections	(Δ/σ)max = 0.001
304 parameters	Δρmax = 0.94 e Å^−3
4 restraints	Δρmin = −1.27 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Pb1	0.030913 (12)	0.835470 (8)	0.138812 (8)	0.00786 (4)
O1	0.1928 (3)	0.62307 (19)	0.21830 (19)	0.0120 (4)
O2	0.2876 (3)	0.79500 (18)	0.21917 (19)	0.0119 (4)
O3	0.8367 (3)	0.7102 (2)	0.40132 (19)	0.0124 (4)
H31	0.765 (6)	0.748 (4)	0.440 (4)	0.024 (10)*
O4	0.0065 (3)	0.98903 (19)	0.25722 (19)	0.0136 (4)
O5	0.1523 (3)	1.03718 (18)	0.05741 (18)	0.0110 (4)
O6	0.0703 (3)	1.3836 (2)	0.3029 (2)	0.0136 (4)
H61	0.111 (7)	1.442 (5)	0.294 (5)	0.042 (15)*
O7	0.6149 (3)	0.7967 (2)	−0.4465 (2)	0.0172 (5)
O8	−0.1509 (3)	0.1982 (2)	0.5265 (2)	0.0168 (4)
H81	−0.066 (6)	0.260 (3)	0.473 (4)	0.057 (16)*
H82	−0.127 (8)	0.204 (5)	0.590 (4)	0.062 (17)*
N1	0.2801 (3)	0.8592 (2)	−0.0646 (2)	0.0106 (5)
N2	0.7553 (4)	0.9791 (3)	−0.4941 (2)	0.0144 (5)
H21	0.830 (5)	0.981 (4)	−0.561 (3)	0.039 (13)*
H22	0.769 (6)	1.035 (3)	−0.471 (4)	0.028 (11)*
C1	0.3015 (4)	0.6828 (3)	0.2424 (2)	0.0088 (5)
C2	0.4561 (4)	0.6274 (2)	0.2976 (2)	0.0090 (5)
C3	0.5721 (4)	0.6960 (3)	0.3251 (2)	0.0093 (5)
H3	0.5529	0.7759	0.3098	0.011*
C4	0.7168 (4)	0.6450 (3)	0.3754 (2)	0.0096 (5)
C5	0.7482 (4)	0.5263 (3)	0.3954 (2)	0.0109 (5)
H5	0.8481	0.4931	0.4262	0.013*
C6	0.6310 (4)	0.4575 (3)	0.3697 (3)	0.0112 (5)
H6	0.6502	0.3775	0.3853	0.013*
C7	0.4846 (4)	0.5077 (3)	0.3203 (2)	0.0096 (5)
H7	0.4063	0.4617	0.3026	0.012*
C8	0.0990 (4)	1.0640 (3)	0.1532 (3)	0.0091 (5)
C9	0.1525 (4)	1.1908 (3)	0.1322 (3)	0.0091 (5)
C10	0.0883 (4)	1.2299 (3)	0.2284 (3)	0.0094 (5)
H10	0.0149	1.1770	0.3063	0.011*
C11	0.1341 (4)	1.3476 (3)	0.2076 (3)	0.0103 (5)
C12	0.2455 (5)	1.4274 (3)	0.0911 (3)	0.0178 (6)
H12	0.2756	1.5067	0.0771	0.021*
C13	0.3106 (5)	1.3867 (3)	−0.0033 (3)	0.0222 (7)
H13	0.3856	1.4392	−0.0808	0.027*
C14	0.2653 (4)	1.2688 (3)	0.0164 (3)	0.0154 (6)
H14	0.3101	1.2422	−0.0473	0.019*
C15	0.4005 (4)	0.9580 (3)	−0.1397 (3)	0.0118 (5)
H15	0.4060	1.0194	−0.1128	0.014*
C16	0.5163 (4)	0.9719 (3)	−0.2555 (3)	0.0118 (5)
H16	0.5959	1.0422	−0.3058	0.014*
C17	0.5126 (4)	0.8796 (3)	−0.2960 (3)	0.0094 (5)
C18	0.3894 (4)	0.7765 (3)	−0.2170 (3)	0.0127 (5)
H18	0.3832	0.7127	−0.2406	0.015*
C19	0.2766 (4)	0.7705 (3)	−0.1032 (3)	0.0116 (5)
H19	0.1946	0.7016	−0.0512	0.014*
C20	0.6331 (4)	0.8831 (3)	−0.4197 (3)	0.0110 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pb1	0.00963 (6)	0.00600 (6)	0.00604 (6)	−0.00059 (4)	−0.00152 (4)	−0.00083 (4)
O1	0.0153 (9)	0.0070 (10)	0.0142 (10)	−0.0003 (7)	−0.0053 (8)	−0.0041 (8)
O2	0.0148 (9)	0.0063 (10)	0.0158 (10)	0.0004 (7)	−0.0071 (8)	−0.0038 (8)
O3	0.0131 (9)	0.0132 (11)	0.0127 (10)	−0.0004 (8)	−0.0023 (8)	−0.0078 (9)
O4	0.0191 (10)	0.0097 (11)	0.0091 (9)	−0.0018 (8)	−0.0011 (8)	−0.0024 (8)
O5	0.0159 (9)	0.0092 (10)	0.0087 (9)	0.0010 (7)	−0.0028 (7)	−0.0051 (8)
O6	0.0170 (10)	0.0095 (11)	0.0140 (10)	−0.0022 (8)	0.0014 (8)	−0.0082 (9)
O7	0.0193 (10)	0.0158 (12)	0.0166 (11)	−0.0039 (8)	0.0024 (8)	−0.0113 (9)
O8	0.0231 (11)	0.0151 (12)	0.0097 (10)	−0.0060 (9)	−0.0013 (8)	−0.0042 (9)
N1	0.0095 (10)	0.0100 (12)	0.0088 (11)	0.0013 (9)	0.0002 (8)	−0.0019 (9)
N2	0.0185 (12)	0.0136 (13)	0.0096 (12)	−0.0024 (10)	0.0021 (9)	−0.0071 (10)
C1	0.0103 (11)	0.0079 (13)	0.0056 (12)	−0.0003 (9)	0.0005 (9)	−0.0019 (10)
C2	0.0117 (12)	0.0067 (13)	0.0059 (12)	−0.0004 (9)	−0.0002 (9)	−0.0013 (10)
C3	0.0122 (12)	0.0058 (13)	0.0068 (12)	−0.0008 (9)	0.0012 (9)	−0.0017 (10)
C4	0.0101 (12)	0.0117 (14)	0.0047 (11)	−0.0016 (10)	0.0007 (9)	−0.0027 (10)
C5	0.0124 (12)	0.0118 (14)	0.0058 (12)	0.0014 (10)	−0.0003 (9)	−0.0023 (11)
C6	0.0157 (13)	0.0072 (13)	0.0091 (12)	0.0014 (10)	−0.0017 (10)	−0.0027 (11)
C7	0.0121 (12)	0.0075 (13)	0.0083 (12)	−0.0011 (10)	−0.0011 (9)	−0.0033 (10)
C8	0.0087 (11)	0.0084 (13)	0.0094 (12)	0.0001 (9)	−0.0023 (9)	−0.0029 (11)
C9	0.0109 (12)	0.0067 (13)	0.0088 (12)	−0.0001 (9)	−0.0031 (10)	−0.0020 (10)
C10	0.0111 (12)	0.0063 (13)	0.0072 (12)	−0.0012 (10)	−0.0011 (9)	0.0001 (10)
C11	0.0113 (12)	0.0105 (14)	0.0102 (13)	0.0017 (10)	−0.0033 (10)	−0.0051 (11)
C12	0.0259 (15)	0.0104 (15)	0.0129 (14)	−0.0044 (12)	−0.0012 (12)	−0.0030 (12)
C13	0.0323 (17)	0.0158 (17)	0.0103 (14)	−0.0101 (13)	0.0053 (12)	−0.0039 (13)
C14	0.0206 (14)	0.0138 (15)	0.0094 (13)	−0.0041 (11)	−0.0001 (11)	−0.0046 (12)
C15	0.0135 (12)	0.0093 (14)	0.0128 (13)	0.0011 (10)	−0.0022 (10)	−0.0058 (11)
C16	0.0112 (12)	0.0094 (14)	0.0113 (13)	−0.0018 (10)	−0.0002 (10)	−0.0021 (11)
C17	0.0092 (11)	0.0096 (14)	0.0087 (12)	0.0005 (10)	−0.0017 (10)	−0.0033 (11)
C18	0.0132 (12)	0.0109 (14)	0.0145 (14)	0.0007 (10)	−0.0020 (10)	−0.0069 (12)
C19	0.0136 (12)	0.0068 (13)	0.0119 (13)	−0.0019 (10)	−0.0019 (10)	−0.0022 (11)
C20	0.0113 (12)	0.0107 (14)	0.0097 (13)	0.0004 (10)	−0.0014 (10)	−0.0037 (11)

Geometric parameters (Å, º)

Pb1—N1	2.564 (2)	C5—C4	1.390 (4)
Pb1—O1	2.753 (2)	C5—C6	1.386 (4)
Pb1—O2	2.317 (2)	C5—H5	0.9300
Pb1—O3^i	2.899 (2)	C6—H6	0.9300
Pb1—O4	2.742 (2)	C7—C2	1.393 (4)
Pb1—O5	2.344 (2)	C7—C6	1.393 (4)
Pb1—O5^ii	2.954 (2)	C7—H7	0.9300
O1—C1	1.253 (3)	C9—C14	1.390 (4)
O2—C1	1.287 (3)	C8—C9	1.501 (4)
O3—C4	1.370 (3)	C10—C9	1.394 (4)
O3—H31	0.86 (4)	C10—H10	0.9300
O4—C8	1.247 (3)	C11—C10	1.382 (4)
O5—C8	1.288 (3)	C11—C12	1.397 (4)
O6—C11	1.361 (3)	C12—C13	1.389 (4)
O6—H61	0.73 (5)	C12—H12	0.9300
O7—C20	1.234 (4)	C13—C14	1.387 (4)
O8—H81	0.89 (2)	C13—H13	0.9300
O8—H82	0.87 (2)	C14—H14	0.9300
N1—C15	1.344 (4)	C15—H15	0.9300
N1—C19	1.334 (4)	C16—C15	1.382 (4)
N2—C20	1.328 (4)	C16—H16	0.9300
N2—H21	0.844 (19)	C17—C16	1.391 (4)
N2—H22	0.843 (19)	C17—C18	1.396 (4)
C1—C2	1.495 (4)	C17—C20	1.510 (4)
C3—C2	1.390 (4)	C18—H18	0.9300
C3—C4	1.390 (4)	C19—C18	1.383 (4)
C3—H3	0.9300	C19—H19	0.9300
O2—Pb1—O1	51.00 (6)	C2—C7—H7	120.2
O2—Pb1—O4	77.71 (7)	C6—C7—H7	120.2
O2—Pb1—O5	85.33 (7)	O4—C8—O5	121.9 (3)
O2—Pb1—N1	83.32 (7)	O4—C8—C9	121.8 (2)
O4—Pb1—O1	121.06 (6)	O5—C8—C9	116.3 (2)
O5—Pb1—O1	132.63 (6)	C10—C9—C8	120.0 (2)
O5—Pb1—O4	50.94 (6)	C14—C9—C8	119.6 (2)
O5—Pb1—N1	77.24 (7)	C14—C9—C10	120.4 (3)
N1—Pb1—O1	79.96 (7)	C11—C10—C9	119.7 (3)
N1—Pb1—O4	125.57 (7)	C11—C10—H10	120.1
C1—O1—Pb1	83.85 (16)	C9—C10—H10	120.1
C1—O2—Pb1	103.41 (16)	O6—C11—C10	118.7 (3)
C4—O3—H31	105 (3)	O6—C11—C12	120.8 (3)
C8—O4—Pb1	84.76 (16)	C10—C11—C12	120.5 (3)
C8—O5—Pb1	102.42 (17)	C11—C12—H12	120.5
C11—O6—H61	116 (4)	C13—C12—C11	119.1 (3)
H82—O8—H81	92 (5)	C13—C12—H12	120.5
C15—N1—Pb1	124.95 (18)	C12—C13—H13	119.5
C19—N1—Pb1	116.64 (18)	C14—C13—C12	120.9 (3)
C19—N1—C15	118.1 (2)	C14—C13—H13	119.5
C20—N2—H21	120 (3)	C9—C14—H14	120.3
C20—N2—H22	120 (3)	C13—C14—C9	119.3 (3)
H22—N2—H21	119 (4)	C13—C14—H14	120.3
O1—C1—O2	121.7 (2)	N1—C15—C16	122.6 (3)
O1—C1—C2	121.4 (2)	N1—C15—H15	118.7
O2—C1—C2	116.9 (2)	C16—C15—H15	118.7
C3—C2—C1	119.8 (2)	C15—C16—C17	119.3 (3)
C3—C2—C7	120.2 (3)	C15—C16—H16	120.3
C7—C2—C1	120.0 (2)	C17—C16—H16	120.3
C2—C3—H3	120.0	C16—C17—C18	117.9 (2)
C4—C3—C2	120.0 (3)	C16—C17—C20	124.5 (3)
C4—C3—H3	120.0	C18—C17—C20	117.6 (3)
O3—C4—C3	121.7 (3)	C17—C18—H18	120.5
O3—C4—C5	118.3 (2)	C19—C18—C17	119.1 (3)
C3—C4—C5	119.9 (3)	C19—C18—H18	120.5
C4—C5—H5	119.9	N1—C19—C18	123.0 (3)
C6—C5—C4	120.1 (3)	N1—C19—H19	118.5
C6—C5—H5	119.9	C18—C19—H19	118.5
C5—C6—C7	120.2 (3)	O7—C20—N2	123.1 (3)
C5—C6—H6	119.9	O7—C20—C17	118.7 (3)
C7—C6—H6	119.9	N2—C20—C17	118.2 (3)
C2—C7—C6	119.6 (3)
O2—Pb1—O1—C1	0.82 (14)	O1—C1—C2—C7	1.7 (4)
O4—Pb1—O1—C1	−35.34 (17)	O2—C1—C2—C3	2.1 (4)
O5—Pb1—O1—C1	28.21 (18)	O2—C1—C2—C7	−177.3 (2)
N1—Pb1—O1—C1	90.32 (16)	C4—C3—C2—C7	−0.1 (4)
O1—Pb1—O2—C1	−0.81 (14)	C4—C3—C2—C1	−179.5 (2)
O4—Pb1—O2—C1	148.04 (17)	C2—C3—C4—O3	178.6 (2)
O5—Pb1—O2—C1	−160.96 (16)	C2—C3—C4—C5	1.6 (4)
N1—Pb1—O2—C1	−83.29 (16)	C6—C5—C4—O3	−179.6 (2)
O1—Pb1—O4—C8	122.11 (16)	C6—C5—C4—C3	−2.4 (4)
O2—Pb1—O4—C8	94.12 (16)	C4—C5—C6—C7	1.8 (4)
O5—Pb1—O4—C8	0.14 (15)	C6—C7—C2—C1	178.8 (2)
N1—Pb1—O4—C8	21.70 (19)	C6—C7—C2—C3	−0.6 (4)
O1—Pb1—O5—C8	−99.11 (17)	C2—C7—C6—C5	−0.3 (4)
O2—Pb1—O5—C8	−78.09 (16)	O4—C8—C9—C10	−4.2 (4)
O4—Pb1—O5—C8	−0.13 (15)	O4—C8—C9—C14	176.1 (3)
N1—Pb1—O5—C8	−162.28 (17)	O5—C8—C9—C10	175.1 (2)
O1—Pb1—N1—C15	−132.2 (2)	O5—C8—C9—C14	−4.5 (4)
O1—Pb1—N1—C19	54.3 (2)	C8—C9—C14—C13	178.5 (3)
O2—Pb1—N1—C15	−80.7 (2)	C10—C9—C14—C13	−1.2 (5)
O2—Pb1—N1—C19	105.8 (2)	C11—C10—C9—C14	1.3 (4)
O4—Pb1—N1—C15	−11.0 (3)	C11—C10—C9—C8	−178.4 (2)
O4—Pb1—N1—C19	175.51 (18)	O6—C11—C10—C9	−179.8 (2)
O5—Pb1—N1—C15	6.0 (2)	C12—C11—C10—C9	−0.5 (4)
O5—Pb1—N1—C19	−167.5 (2)	O6—C11—C12—C13	178.9 (3)
Pb1—O1—C1—O2	−1.3 (2)	C10—C11—C12—C13	−0.4 (5)
Pb1—O1—C1—C2	179.7 (2)	C11—C12—C13—C14	0.5 (5)
Pb1—O2—C1—O1	1.6 (3)	C12—C13—C14—C9	0.3 (5)
Pb1—O2—C1—C2	−179.40 (18)	C17—C16—C15—N1	−1.4 (4)
Pb1—O4—C8—O5	−0.2 (2)	C18—C17—C16—C15	0.5 (4)
Pb1—O4—C8—C9	179.1 (2)	C20—C17—C16—C15	−179.4 (3)
Pb1—O5—C8—O4	0.3 (3)	C16—C17—C18—C19	0.3 (4)
Pb1—O5—C8—C9	−179.06 (19)	C20—C17—C18—C19	−179.8 (3)
Pb1—N1—C15—C16	−172.0 (2)	C16—C17—C20—O7	−178.6 (3)
C19—N1—C15—C16	1.5 (4)	C16—C17—C20—N2	1.9 (4)
Pb1—N1—C19—C18	173.3 (2)	C18—C17—C20—O7	1.5 (4)
C15—N1—C19—C18	−0.7 (4)	C18—C17—C20—N2	−177.9 (3)
O1—C1—C2—C3	−178.9 (2)	N1—C19—C18—C17	−0.2 (4)

Symmetry codes: (i) x−1, y, z; (ii) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O4^iii	0.84 (4)	2.21 (4)	3.046 (3)	175 (4)
N2—H22···O8^iv	0.85 (4)	2.06 (4)	2.880 (5)	162 (4)
O3—H31···O7^v	0.86 (5)	1.81 (5)	2.646 (3)	166 (4)
O6—H61···O1^vi	0.73 (6)	2.05 (6)	2.755 (4)	161 (6)
O8—H81···O6^vii	0.89 (4)	2.02 (4)	2.846 (3)	154 (4)
O8—H82···O2^viii	0.87 (5)	2.31 (5)	3.018 (3)	139 (5)
O8—H82···O3^ix	0.87 (5)	2.44 (6)	3.054 (3)	128 (4)
C12—H12···O1^vi	0.93	2.57	3.269 (4)	132
C15—H15···O5	0.93	2.46	3.060 (4)	122
C16—H16···O8^iv	0.93	2.51	3.413 (4)	165

Symmetry codes: (iii) x+1, y, z−1; (iv) x+1, y+1, z−1; (v) x, y, z+1; (vi) x, y+1, z; (vii) x, y−1, z; (viii) −x, −y+1, −z+1; (ix) −x+1, −y+1, −z+1.