Bis[N-(4-chloro-phen-yl)pyridine-3-carboxamide]-silver(I) nitrate.

In the title compound, [Ag(C(12)H(9)ClN(2)O)(2)]NO(3), two N atoms from two pyridine rings of two N-(4-chloro-phen-yl)pyridine-3-carboxamide ligands coordinate to the Ag(I) atom, forming a nearly linear geometry with an N-Ag-N angle of 173.41 (7)°. The crystal structure is stabilized by N-H⋯O, C-H⋯O and C-H⋯Cl hydrogen bonds and π-π stacking inter-actions [centroid-centroid distance = 3.5469 (16) Å] between the pyridyl and benzene rings. The shortest Ag⋯Ag distance is 3.2574 (5) Å.

Related literature

For general background to metal-organic complexes with pyridyl carboxamide ligands, see: Noveron et al. (2002 ▶); Zhang et al. (2002 ▶); Mondal et al. (2004 ▶); Jacob & Mukherjee (2006 ▶). For related structures and the synthesis of the title ligand, see: Shi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

[Ag(C12H9ClN2O)2]NO3

M = 635.20

Triclinic,

a = 10.0745 (10) Å

b = 10.1425 (10) Å

c = 13.473 (2) Å

α = 107.515 (2)°

β = 102.602 (2)°

γ = 103.706 (1)°

V = 1211.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.10 mm−1

T = 296 K

0.24 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.776, T max = 0.820

6194 measured reflections

4232 independent reflections

3848 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.064

S = 1.05

4232 reflections

334 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.39 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810025511/zl2286sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025511/zl2286Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ag(C12H9ClN2O)2]NO3	Z = 2
Mr = 635.20	F(000) = 636
Triclinic, P1	Dx = 1.741 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0745 (10) Å	Cell parameters from 4853 reflections
b = 10.1425 (10) Å	θ = 2.2–27.8°
c = 13.473 (2) Å	µ = 1.10 mm−1
α = 107.515 (2)°	T = 296 K
β = 102.602 (2)°	Block, colourless
γ = 103.706 (1)°	0.24 × 0.23 × 0.18 mm
V = 1211.6 (2) Å3

Bruker APEXII CCD area-detector diffractometer	4232 independent reflections
Radiation source: fine-focus sealed tube	3848 reflections with I > 2σ(I)
graphite	Rint = 0.014
phi and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.776, Tmax = 0.820	k = −12→11
6194 measured reflections	l = −7→16

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0278P)2 + 0.6379P] where P = (Fo2 + 2Fc2)/3
4232 reflections	(Δ/σ)max = 0.002
334 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ag1	0.87169 (2)	0.56734 (2)	0.518117 (14)	0.04869 (8)
Cl1	0.58438 (8)	0.45918 (8)	−0.36615 (5)	0.05917 (18)
Cl2	1.33119 (13)	1.05319 (10)	1.51069 (6)	0.0891 (3)
N2	0.64188 (19)	0.3727 (2)	0.05514 (14)	0.0375 (4)
H1	0.7178	0.4325	0.1077	0.045*
O1	0.44206 (18)	0.17952 (18)	0.01256 (13)	0.0507 (4)
N3	0.9912 (2)	0.7669 (2)	0.65614 (15)	0.0402 (4)
N1	0.7302 (2)	0.3744 (2)	0.38083 (14)	0.0388 (4)
C6	0.5572 (2)	0.2683 (2)	0.07732 (17)	0.0356 (5)
C7	0.6197 (2)	0.3948 (2)	−0.04546 (17)	0.0347 (5)
N4	1.2066 (2)	0.9810 (2)	1.04496 (15)	0.0417 (5)
H2	1.2615	1.0478	1.0314	0.050*
C8	0.4900 (2)	0.3301 (3)	−0.12996 (18)	0.0406 (5)
H7	0.4103	0.2727	−0.1208	0.049*
C3	0.7042 (2)	0.2420 (3)	0.38709 (19)	0.0422 (5)
H4	0.7352	0.2354	0.4551	0.051*
C2	0.6833 (2)	0.3825 (2)	0.28185 (17)	0.0355 (5)
H3	0.6993	0.4742	0.2771	0.043*
C13	1.0816 (2)	0.8926 (2)	0.85119 (18)	0.0355 (5)
O2	1.0207 (2)	0.7703 (2)	0.96688 (15)	0.0770 (7)
C16	1.0810 (3)	1.0276 (3)	0.7337 (2)	0.0457 (6)
H13	1.1003	1.1159	0.7233	0.055*
C5	0.5870 (2)	0.1236 (2)	0.19497 (18)	0.0378 (5)
H6	0.5396	0.0392	0.1327	0.045*
C4	0.6329 (2)	0.1148 (3)	0.29612 (19)	0.0412 (5)
H5	0.6161	0.0243	0.3031	0.049*
N5	0.9683 (2)	0.6282 (2)	0.31338 (17)	0.0501 (5)
C1	0.6126 (2)	0.2601 (2)	0.18731 (17)	0.0333 (5)
C23	1.3156 (2)	1.1510 (3)	1.34542 (19)	0.0412 (5)
H17	1.3479	1.2442	1.3993	0.049*
C17	1.1113 (2)	1.0260 (2)	0.8381 (2)	0.0413 (5)
H14	1.1510	1.1130	0.8989	0.050*
C9	0.4794 (3)	0.3512 (2)	−0.22784 (19)	0.0421 (5)
H8	0.3927	0.3077	−0.2846	0.050*
C15	1.0219 (3)	0.8970 (3)	0.6450 (2)	0.0453 (6)
H12	1.0026	0.8990	0.5749	0.054*
C10	0.5971 (3)	0.4366 (2)	−0.24093 (18)	0.0404 (5)
C24	1.2834 (2)	1.1322 (2)	1.23596 (18)	0.0365 (5)
H18	1.2933	1.2132	1.2159	0.044*
C22	1.2991 (3)	1.0296 (3)	1.37339 (19)	0.0453 (6)
C14	1.0215 (2)	0.7664 (2)	0.75782 (17)	0.0361 (5)
H11	1.0012	0.6767	0.7662	0.043*
C19	1.2365 (2)	0.9934 (2)	1.15612 (18)	0.0359 (5)
O5	0.9102 (3)	0.7052 (2)	0.3672 (2)	0.0828 (7)
C11	0.7258 (3)	0.5049 (3)	−0.1567 (2)	0.0482 (6)
H9	0.8045	0.5640	−0.1658	0.058*
C20	1.2222 (3)	0.8724 (3)	1.1858 (2)	0.0440 (6)
H15	1.1914	0.7791	1.1323	0.053*
C18	1.1008 (2)	0.8748 (3)	0.95936 (19)	0.0411 (5)
C12	0.7364 (3)	0.4844 (2)	−0.05886 (19)	0.0434 (5)
H10	0.8224	0.5309	−0.0015	0.052*
O3	1.0717 (3)	0.6017 (3)	0.3604 (2)	0.0869 (7)
C21	1.2540 (3)	0.8910 (3)	1.2953 (2)	0.0475 (6)
H16	1.2450	0.8105	1.3159	0.057*
O4	0.9214 (2)	0.5770 (3)	0.21319 (16)	0.0913 (8)

	U11	U22	U33	U12	U13	U23
Ag1	0.05203 (13)	0.04686 (12)	0.03000 (11)	0.00860 (9)	0.00232 (8)	0.00417 (8)
Cl1	0.0777 (5)	0.0579 (4)	0.0394 (3)	0.0099 (3)	0.0166 (3)	0.0252 (3)
Cl2	0.1476 (9)	0.0747 (5)	0.0392 (4)	0.0264 (5)	0.0197 (5)	0.0274 (4)
N2	0.0337 (9)	0.0385 (10)	0.0285 (9)	−0.0010 (8)	0.0017 (8)	0.0120 (8)
O1	0.0446 (9)	0.0506 (10)	0.0358 (9)	−0.0106 (8)	−0.0024 (7)	0.0180 (8)
N3	0.0381 (10)	0.0429 (11)	0.0332 (10)	0.0096 (8)	0.0069 (8)	0.0113 (8)
N1	0.0409 (10)	0.0396 (10)	0.0298 (9)	0.0097 (8)	0.0061 (8)	0.0109 (8)
C6	0.0361 (12)	0.0344 (11)	0.0296 (11)	0.0061 (9)	0.0065 (9)	0.0095 (9)
C7	0.0369 (11)	0.0315 (11)	0.0299 (10)	0.0066 (9)	0.0072 (9)	0.0095 (9)
N4	0.0408 (10)	0.0384 (10)	0.0321 (10)	−0.0039 (8)	0.0060 (8)	0.0115 (8)
C8	0.0357 (12)	0.0432 (13)	0.0367 (12)	0.0035 (10)	0.0078 (10)	0.0163 (10)
C3	0.0421 (13)	0.0488 (14)	0.0359 (12)	0.0122 (11)	0.0085 (10)	0.0207 (11)
C2	0.0355 (11)	0.0345 (11)	0.0335 (11)	0.0086 (9)	0.0077 (9)	0.0130 (9)
C13	0.0273 (10)	0.0388 (12)	0.0352 (11)	0.0065 (9)	0.0086 (9)	0.0109 (10)
O2	0.0791 (14)	0.0669 (13)	0.0411 (10)	−0.0345 (11)	0.0039 (10)	0.0162 (9)
C16	0.0442 (13)	0.0392 (13)	0.0535 (15)	0.0114 (11)	0.0103 (11)	0.0221 (11)
C5	0.0347 (11)	0.0353 (12)	0.0368 (12)	0.0069 (9)	0.0081 (9)	0.0102 (9)
C4	0.0404 (12)	0.0392 (12)	0.0455 (13)	0.0113 (10)	0.0108 (10)	0.0212 (11)
N5	0.0533 (13)	0.0433 (12)	0.0390 (11)	−0.0037 (10)	0.0013 (10)	0.0199 (10)
C1	0.0293 (10)	0.0371 (11)	0.0303 (11)	0.0072 (9)	0.0083 (9)	0.0117 (9)
C23	0.0435 (13)	0.0369 (12)	0.0353 (12)	0.0097 (10)	0.0092 (10)	0.0075 (10)
C17	0.0361 (12)	0.0350 (12)	0.0436 (13)	0.0068 (10)	0.0077 (10)	0.0091 (10)
C9	0.0431 (13)	0.0398 (12)	0.0346 (12)	0.0077 (10)	0.0035 (10)	0.0127 (10)
C15	0.0441 (13)	0.0514 (14)	0.0406 (13)	0.0141 (11)	0.0079 (11)	0.0220 (11)
C10	0.0531 (14)	0.0359 (12)	0.0309 (11)	0.0107 (10)	0.0127 (10)	0.0140 (9)
C24	0.0335 (11)	0.0338 (11)	0.0379 (12)	0.0061 (9)	0.0076 (9)	0.0138 (10)
C22	0.0524 (14)	0.0493 (14)	0.0349 (12)	0.0161 (11)	0.0109 (11)	0.0188 (11)
C14	0.0320 (11)	0.0348 (11)	0.0346 (11)	0.0057 (9)	0.0070 (9)	0.0102 (9)
C19	0.0297 (11)	0.0380 (12)	0.0339 (11)	0.0055 (9)	0.0067 (9)	0.0114 (9)
O5	0.114 (2)	0.0582 (13)	0.0899 (17)	0.0286 (13)	0.0503 (16)	0.0324 (12)
C11	0.0481 (14)	0.0441 (13)	0.0467 (14)	0.0004 (11)	0.0147 (11)	0.0206 (11)
C20	0.0491 (14)	0.0333 (12)	0.0439 (13)	0.0108 (10)	0.0120 (11)	0.0103 (10)
C18	0.0377 (12)	0.0408 (12)	0.0333 (11)	0.0002 (10)	0.0101 (10)	0.0086 (10)
C12	0.0381 (12)	0.0411 (13)	0.0371 (12)	−0.0018 (10)	0.0032 (10)	0.0131 (10)
O3	0.0772 (15)	0.0788 (15)	0.0962 (18)	0.0178 (12)	−0.0082 (13)	0.0520 (14)
C21	0.0557 (15)	0.0424 (13)	0.0474 (14)	0.0157 (11)	0.0136 (12)	0.0227 (11)
O4	0.0622 (13)	0.129 (2)	0.0382 (11)	−0.0217 (13)	−0.0009 (10)	0.0228 (12)

Ag1—N3	2.1467 (19)	C16—C15	1.379 (3)
Ag1—N1	2.1519 (18)	C16—C17	1.379 (3)
Ag1—Ag1i	3.2574 (5)	C16—H13	0.9300
Cl1—C10	1.751 (2)	C5—C4	1.377 (3)
Cl2—C22	1.738 (2)	C5—C1	1.386 (3)
N2—C6	1.346 (3)	C5—H6	0.9300
N2—C7	1.419 (3)	C4—H5	0.9300
N2—H1	0.8600	N5—O4	1.224 (3)
O1—C6	1.228 (3)	N5—O3	1.228 (3)
N3—C14	1.339 (3)	N5—O5	1.240 (3)
N3—C15	1.343 (3)	C23—C22	1.377 (3)
N1—C3	1.338 (3)	C23—C24	1.382 (3)
N1—C2	1.348 (3)	C23—H17	0.9300
C6—C1	1.499 (3)	C17—H14	0.9300
C7—C12	1.388 (3)	C9—C10	1.373 (3)
C7—C8	1.389 (3)	C9—H8	0.9300
N4—C18	1.341 (3)	C15—H12	0.9300
N4—C19	1.422 (3)	C10—C11	1.381 (3)
N4—H2	0.8600	C24—C19	1.384 (3)
C8—C9	1.384 (3)	C24—H18	0.9300
C8—H7	0.9300	C22—C21	1.374 (3)
C3—C4	1.381 (3)	C14—H11	0.9300
C3—H4	0.9300	C19—C20	1.387 (3)
C2—C1	1.380 (3)	C11—C12	1.381 (3)
C2—H3	0.9300	C11—H9	0.9300
C13—C14	1.385 (3)	C20—C21	1.383 (3)
C13—C17	1.387 (3)	C20—H15	0.9300
C13—C18	1.499 (3)	C12—H10	0.9300
O2—C18	1.216 (3)	C21—H16	0.9300
N3—Ag1—N1	173.41 (7)	C2—C1—C5	118.5 (2)
N3—Ag1—Ag1i	100.45 (5)	C2—C1—C6	122.95 (19)
N1—Ag1—Ag1i	86.14 (5)	C5—C1—C6	118.50 (19)
C6—N2—C7	127.13 (18)	C22—C23—C24	118.9 (2)
C6—N2—H1	116.4	C22—C23—H17	120.5
C7—N2—H1	116.4	C24—C23—H17	120.5
C14—N3—C15	117.8 (2)	C16—C17—C13	119.1 (2)
C14—N3—Ag1	120.15 (15)	C16—C17—H14	120.5
C15—N3—Ag1	121.49 (16)	C13—C17—H14	120.5
C3—N1—C2	118.20 (19)	C10—C9—C8	119.8 (2)
C3—N1—Ag1	121.23 (15)	C10—C9—H8	120.1
C2—N1—Ag1	119.84 (15)	C8—C9—H8	120.1
O1—C6—N2	124.0 (2)	N3—C15—C16	122.5 (2)
O1—C6—C1	119.57 (19)	N3—C15—H12	118.8
N2—C6—C1	116.38 (18)	C16—C15—H12	118.8
C12—C7—C8	119.4 (2)	C9—C10—C11	120.9 (2)
C12—C7—N2	116.96 (19)	C9—C10—Cl1	119.65 (18)
C8—C7—N2	123.61 (19)	C11—C10—Cl1	119.43 (18)
C18—N4—C19	126.02 (19)	C23—C24—C19	120.3 (2)
C18—N4—H2	117.0	C23—C24—H18	119.9
C19—N4—H2	117.0	C19—C24—H18	119.9
C9—C8—C7	120.0 (2)	C21—C22—C23	121.6 (2)
C9—C8—H7	120.0	C21—C22—Cl2	119.61 (19)
C7—C8—H7	120.0	C23—C22—Cl2	118.78 (19)
N1—C3—C4	122.4 (2)	N3—C14—C13	123.3 (2)
N1—C3—H4	118.8	N3—C14—H11	118.3
C4—C3—H4	118.8	C13—C14—H11	118.3
N1—C2—C1	122.6 (2)	C24—C19—C20	120.0 (2)
N1—C2—H3	118.7	C24—C19—N4	117.7 (2)
C1—C2—H3	118.7	C20—C19—N4	122.3 (2)
C14—C13—C17	118.0 (2)	C12—C11—C10	119.3 (2)
C14—C13—C18	117.1 (2)	C12—C11—H9	120.3
C17—C13—C18	124.7 (2)	C10—C11—H9	120.3
C15—C16—C17	119.3 (2)	C21—C20—C19	119.8 (2)
C15—C16—H13	120.4	C21—C20—H15	120.1
C17—C16—H13	120.4	C19—C20—H15	120.1
C4—C5—C1	119.1 (2)	O2—C18—N4	123.4 (2)
C4—C5—H6	120.5	O2—C18—C13	120.3 (2)
C1—C5—H6	120.5	N4—C18—C13	116.31 (19)
C5—C4—C3	119.2 (2)	C11—C12—C7	120.5 (2)
C5—C4—H5	120.4	C11—C12—H10	119.8
C3—C4—H5	120.4	C7—C12—H10	119.8
O4—N5—O3	119.8 (3)	C22—C21—C20	119.4 (2)
O4—N5—O5	120.0 (3)	C22—C21—H16	120.3
O3—N5—O5	120.1 (3)	C20—C21—H16	120.3
Ag1i—Ag1—N3—C14	−83.05 (17)	C17—C16—C15—N3	0.5 (4)
Ag1i—Ag1—N3—C15	105.37 (18)	C8—C9—C10—C11	−1.5 (4)
Ag1i—Ag1—N1—C3	66.84 (17)	C8—C9—C10—Cl1	178.39 (19)
Ag1i—Ag1—N1—C2	−103.19 (16)	C22—C23—C24—C19	−0.6 (4)
C7—N2—C6—O1	−3.7 (4)	C24—C23—C22—C21	1.2 (4)
C7—N2—C6—C1	174.4 (2)	C24—C23—C22—Cl2	−176.88 (19)
C6—N2—C7—C12	−164.4 (2)	C15—N3—C14—C13	0.4 (3)
C6—N2—C7—C8	14.4 (4)	Ag1—N3—C14—C13	−171.44 (16)
C12—C7—C8—C9	2.2 (4)	C17—C13—C14—N3	0.2 (3)
N2—C7—C8—C9	−176.6 (2)	C18—C13—C14—N3	176.3 (2)
C2—N1—C3—C4	0.7 (3)	C23—C24—C19—C20	−0.3 (3)
Ag1—N1—C3—C4	−169.49 (18)	C23—C24—C19—N4	−179.3 (2)
C3—N1—C2—C1	−1.3 (3)	C18—N4—C19—C24	−143.7 (2)
Ag1—N1—C2—C1	169.04 (16)	C18—N4—C19—C20	37.3 (4)
C1—C5—C4—C3	−0.5 (3)	C9—C10—C11—C12	1.2 (4)
N1—C3—C4—C5	0.2 (4)	Cl1—C10—C11—C12	−178.6 (2)
N1—C2—C1—C5	1.0 (3)	C24—C19—C20—C21	0.4 (4)
N1—C2—C1—C6	178.6 (2)	N4—C19—C20—C21	179.4 (2)
C4—C5—C1—C2	0.0 (3)	C19—N4—C18—O2	−3.9 (4)
C4—C5—C1—C6	−177.8 (2)	C19—N4—C18—C13	174.3 (2)
O1—C6—C1—C2	−142.3 (2)	C14—C13—C18—O2	−28.4 (3)
N2—C6—C1—C2	39.6 (3)	C17—C13—C18—O2	147.4 (3)
O1—C6—C1—C5	35.4 (3)	C14—C13—C18—N4	153.3 (2)
N2—C6—C1—C5	−142.8 (2)	C17—C13—C18—N4	−30.8 (3)
C15—C16—C17—C13	0.1 (4)	C10—C11—C12—C7	0.8 (4)
C14—C13—C17—C16	−0.4 (3)	C8—C7—C12—C11	−2.5 (4)
C18—C13—C17—C16	−176.2 (2)	N2—C7—C12—C11	176.4 (2)
C7—C8—C9—C10	−0.3 (4)	C23—C22—C21—C20	−1.1 (4)
C14—N3—C15—C16	−0.8 (4)	Cl2—C22—C21—C20	177.0 (2)
Ag1—N3—C15—C16	170.97 (18)	C19—C20—C21—C22	0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O4	0.86	2.10	2.953 (3)	169
N4—H2···O1ii	0.86	2.10	2.931 (3)	162
C2—H3···O5	0.93	2.51	3.210 (3)	133
C3—H4···O3i	0.93	2.57	3.300 (3)	136
C4—H5···Cl2iii	0.93	2.83	3.516 (3)	132
C5—H6···O1iv	0.93	2.55	3.376 (3)	148
C8—H7···O1	0.93	2.27	2.841 (3)	119
C11—H9···O2v	0.93	2.49	3.194 (4)	132
C16—H13···O5vi	0.93	2.48	3.370 (4)	160
C20—H15···O2	0.93	2.46	2.906 (3)	109

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O4	0.86	2.10	2.953 (3)	169
N4—H2⋯O1i	0.86	2.10	2.931 (3)	162
C2—H3⋯O5	0.93	2.51	3.210 (3)	133
C3—H4⋯O3ii	0.93	2.57	3.300 (3)	136
C4—H5⋯Cl2iii	0.93	2.83	3.516 (3)	132
C5—H6⋯O1iv	0.93	2.55	3.376 (3)	148
C8—H7⋯O1	0.93	2.27	2.841 (3)	119
C11—H9⋯O2v	0.93	2.49	3.194 (4)	132
C16—H13⋯O5vi	0.93	2.48	3.370 (4)	160
C20—H15⋯O2	0.93	2.46	2.906 (3)	109

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .