(5,10,15,20-Tetra-phenyl-porphyrinato-κ(4) N)zinc-18-crown-6 (1/1).

In the title compound, [Zn(C44H28N4)]·C12H24O6, the Zn(II) ion lies on an inversion center and the asymmetric unit contains one half of a Zn(TPP) complex (TPP = 5,10,15,20-tetra-phenyl-porphyrin dianion) and one half of a centrosymmetric 18-crown-6 mol-ecule. The Zn(TPP) complex exhibits a nearly planar conformation of the porphyrin core [maximum deviation = 0.106 (2) Å] with an average Zn-N distance of 2.047 (2) Å. The title compound is considered as a one-dimensional polymer along [010], in which the Zn(TPP) moiety is linked to the closest O atoms of two symmetry-related 18-crown-6 mol-ecules with a Zn-O distance of 2.582 (1) Å, completing a distorted octahedral coordination environment of the metal ion. The chains are mainly sustained by weak C-H⋯π inter-actions. An ethyl-ene group of the 18-crown-6 mol-ecule is disordered over three sites with occupancies of 0.50, 0.25 and 0.25.

Related literature

For related structures, see: Cheng & Scheidt (1995 ▶); Diskin-Posner et al. (1999 ▶); Ezzayani et al. (2013 ▶); Kojima et al. (2009 ▶); Kumar et al. (1997 ▶); Mansour et al. (2010 ▶); Ricard et al. (2001 ▶); Suijkerbuijk et al. (2007 ▶); Toumi et al. (2013 ▶). For the SIMU/ISOR restraints used in the refinement, see: McArdle (1995 ▶). For a description of the Cambridge Strcutural Database, see: Allen (2002 ▶). For the synthesis, see: Oberda et al. (2011 ▶).

Experimental

Crystal data

[Zn(C44H28N4)]·C12H24O6

M = 942.39

Triclinic,

a = 10.2170 (3) Å

b = 11.1190 (4) Å

c = 11.8243 (3) Å

α = 104.384 (3)°

β = 105.912 (3)°

γ = 108.096 (3)°

V = 1143.23 (8) Å3

Z = 1

Mo Kα radiation

μ = 0.60 mm−1

T = 180 K

0.48 × 0.45 × 0.33 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.918, T max = 1.000

22963 measured reflections

4503 independent reflections

3774 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.07

4503 reflections

310 parameters

30 restraints

H-atom parameters constrained

Δρmax = 0.95 e Å−3

Δρmin = −0.67 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2010 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 2012) ▶; software used to prepare material for publication: WinGX (Farrugia, 2012) ▶.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813018126/hy2633sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018126/hy2633Isup2.hkl

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

[Zn(C44H28N4)]·C12H24O6	Z = 1
Mr = 942.39	F(000) = 494
Triclinic, P1	Dx = 1.369 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2170 (3) Å	Cell parameters from 13909 reflections
b = 11.1190 (4) Å	θ = 3.3–29.1°
c = 11.8243 (3) Å	µ = 0.60 mm−1
α = 104.384 (3)°	T = 180 K
β = 105.912 (3)°	Block, violet
γ = 108.096 (3)°	0.48 × 0.45 × 0.33 mm
V = 1143.23 (8) Å3

Oxford Diffraction Xcalibur diffractometer	4503 independent reflections
Radiation source: fine-focus sealed tube	3774 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 16.1978 pixels mm-1	θmax = 26.0°, θmin = 3.3°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −13→13
Tmin = 0.918, Tmax = 1.000	l = −14→14
22963 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0591P)2 + 0.5621P] where P = (Fo2 + 2Fc2)/3
4503 reflections	(Δ/σ)max < 0.001
310 parameters	Δρmax = 0.95 e Å−3
30 restraints	Δρmin = −0.67 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
Zn	1.0000	0.0000	0.5000	0.03274 (14)
N1	1.11054 (18)	−0.01373 (18)	0.66650 (15)	0.0230 (4)
N2	0.79951 (17)	−0.10495 (17)	0.50470 (15)	0.0213 (3)
C1	1.2617 (2)	0.0346 (2)	0.72913 (18)	0.0219 (4)
C2	1.2919 (2)	−0.0065 (2)	0.83665 (19)	0.0248 (4)
H2	1.3854	0.0140	0.8949	0.030*
C3	1.1598 (2)	−0.0801 (2)	0.83723 (18)	0.0243 (4)
H3	1.1450	−0.1199	0.8958	0.029*
C4	1.0454 (2)	−0.0857 (2)	0.72994 (18)	0.0215 (4)
C5	0.8921 (2)	−0.1589 (2)	0.69362 (18)	0.0214 (4)
C6	0.7795 (2)	−0.1682 (2)	0.58835 (18)	0.0217 (4)
C7	0.6231 (2)	−0.2468 (2)	0.5519 (2)	0.0274 (5)
H7	0.5805	−0.2996	0.5927	0.033*
C8	0.5497 (2)	−0.2298 (2)	0.4477 (2)	0.0270 (4)
H8	0.4471	−0.2677	0.4038	0.032*
C9	0.6606 (2)	−0.1415 (2)	0.41709 (18)	0.0215 (4)
C10	1.3700 (2)	0.1076 (2)	0.69132 (18)	0.0221 (4)
C11	0.8443 (2)	−0.2378 (2)	0.77232 (18)	0.0218 (4)
C12	0.8211 (3)	−0.3733 (2)	0.7389 (2)	0.0355 (5)
H12	0.8369	−0.4151	0.6684	0.043*
C13	0.7744 (3)	−0.4473 (2)	0.8098 (2)	0.0382 (6)
H13	0.7593	−0.5383	0.7867	0.046*
C14	0.7504 (2)	−0.3870 (2)	0.9138 (2)	0.0318 (5)
H14	0.7190	−0.4368	0.9611	0.038*
C15	0.7733 (3)	−0.2519 (2)	0.9478 (2)	0.0338 (5)
H15	0.7569	−0.2105	1.0181	0.041*
C16	0.8207 (2)	−0.1776 (2)	0.8774 (2)	0.0288 (5)
H16	0.8366	−0.0864	0.9013	0.035*
C17	1.5297 (2)	0.1524 (2)	0.77206 (18)	0.0228 (4)
C18	1.6208 (2)	0.1016 (2)	0.7256 (2)	0.0303 (5)
H18	1.5813	0.0383	0.6437	0.036*
C19	1.7692 (3)	0.1441 (3)	0.7995 (2)	0.0373 (5)
H19	1.8287	0.1094	0.7672	0.045*
C20	1.8297 (2)	0.2382 (3)	0.9214 (2)	0.0366 (6)
H20	1.9298	0.2674	0.9706	0.044*
C21	1.7406 (2)	0.2884 (2)	0.9696 (2)	0.0337 (5)
H21	1.7805	0.3507	1.0519	0.040*
C22	1.59147 (13)	0.24577 (12)	0.89529 (11)	0.0270 (4)
H22	1.5321	0.2801	0.9283	0.032*
O1	0.99283 (13)	−0.23197 (12)	0.38069 (11)	0.0414 (4)
C23	0.88485 (13)	−0.30609 (12)	0.25589 (11)	0.0415 (6)
H23A	0.9247	−0.3582	0.2072	0.050*
H23B	0.8669	−0.2424	0.2171	0.050*
C24	0.7397 (3)	−0.4009 (3)	0.2491 (2)	0.0423 (6)
H24A	0.7125	−0.3563	0.3149	0.051*
H24B	0.6622	−0.4252	0.1681	0.051*
O2	0.7523 (2)	−0.51824 (18)	0.26441 (18)	0.0450 (4)
C25	0.6304 (3)	−0.6046 (3)	0.2816 (3)	0.0473 (6)
H25A	0.5470	−0.6566	0.2012	0.057*
H25B	0.5991	−0.5509	0.3380	0.057*
C26	0.6787 (3)	−0.6981 (3)	0.3367 (3)	0.0510 (7)
H26A	0.5923	−0.7734	0.3282	0.061*
H26B	0.7329	−0.7344	0.2921	0.061*
O3	0.7692 (2)	−0.6263 (2)	0.4630 (2)	0.0602 (5)
C27A	0.9180 (7)	−0.6327 (7)	0.5200 (6)	0.0541 (7)	0.50
H27A	0.9569	−0.6576	0.4558	0.065*	0.50
H27B	0.9902	−0.5461	0.5848	0.065*	0.50
C28A	0.8820 (7)	−0.7408 (7)	0.5755 (6)	0.0492 (8)	0.50
H28A	0.8521	−0.7103	0.6447	0.059*	0.50
H28B	0.7999	−0.8229	0.5118	0.059*	0.50
C27B	0.8033 (15)	−0.7226 (13)	0.5251 (14)	0.0541 (7)	0.25
H27C	0.7839	−0.7096	0.6022	0.065*	0.25
H27D	0.7453	−0.8165	0.4685	0.065*	0.25
C28B	0.9557 (13)	−0.6854 (13)	0.5508 (13)	0.0492 (8)	0.25
H28C	1.0109	−0.5895	0.6021	0.059*	0.25
H28D	0.9724	−0.7018	0.4725	0.059*	0.25
C27C	0.8191 (15)	−0.7395 (13)	0.4715 (13)	0.0541 (7)	0.25
H27E	0.7387	−0.8215	0.4604	0.065*	0.25
H27F	0.8663	−0.7600	0.4127	0.065*	0.25
C28C	0.9287 (15)	−0.6667 (14)	0.6059 (12)	0.0492 (8)	0.25
H28E	0.8790	−0.6567	0.6645	0.059*	0.25
H28F	0.9991	−0.5779	0.6184	0.059*	0.25

	U11	U22	U33	U12	U13	U23
Zn	0.01801 (19)	0.0560 (3)	0.0266 (2)	0.00947 (17)	0.00743 (14)	0.02734 (18)
N1	0.0178 (8)	0.0310 (9)	0.0204 (8)	0.0074 (7)	0.0065 (7)	0.0138 (7)
N2	0.0182 (8)	0.0277 (9)	0.0180 (8)	0.0078 (7)	0.0058 (6)	0.0116 (7)
C1	0.0206 (9)	0.0250 (10)	0.0183 (9)	0.0085 (8)	0.0049 (8)	0.0089 (8)
C2	0.0232 (10)	0.0294 (11)	0.0200 (10)	0.0106 (9)	0.0040 (8)	0.0110 (8)
C3	0.0257 (10)	0.0285 (11)	0.0191 (9)	0.0102 (9)	0.0066 (8)	0.0125 (8)
C4	0.0234 (10)	0.0252 (10)	0.0176 (9)	0.0098 (8)	0.0080 (8)	0.0103 (8)
C5	0.0249 (10)	0.0227 (10)	0.0185 (9)	0.0091 (8)	0.0105 (8)	0.0091 (8)
C6	0.0217 (10)	0.0245 (10)	0.0198 (9)	0.0076 (8)	0.0101 (8)	0.0096 (8)
C7	0.0226 (10)	0.0338 (12)	0.0268 (11)	0.0072 (9)	0.0112 (9)	0.0158 (9)
C8	0.0188 (10)	0.0318 (11)	0.0272 (11)	0.0057 (9)	0.0078 (8)	0.0127 (9)
C9	0.0184 (9)	0.0255 (10)	0.0198 (9)	0.0077 (8)	0.0070 (8)	0.0091 (8)
C10	0.0199 (9)	0.0244 (10)	0.0201 (9)	0.0088 (8)	0.0054 (8)	0.0082 (8)
C11	0.0181 (9)	0.0258 (10)	0.0194 (9)	0.0054 (8)	0.0055 (8)	0.0113 (8)
C12	0.0522 (15)	0.0290 (12)	0.0245 (11)	0.0139 (11)	0.0175 (10)	0.0089 (9)
C13	0.0504 (15)	0.0233 (11)	0.0313 (12)	0.0065 (11)	0.0106 (11)	0.0109 (10)
C14	0.0276 (11)	0.0368 (13)	0.0288 (11)	0.0050 (10)	0.0084 (9)	0.0213 (10)
C15	0.0431 (13)	0.0442 (14)	0.0296 (11)	0.0230 (11)	0.0229 (10)	0.0214 (10)
C16	0.0379 (12)	0.0288 (11)	0.0281 (11)	0.0163 (10)	0.0170 (9)	0.0152 (9)
C17	0.0202 (10)	0.0256 (10)	0.0225 (10)	0.0072 (8)	0.0060 (8)	0.0137 (8)
C18	0.0275 (11)	0.0339 (12)	0.0295 (11)	0.0125 (10)	0.0107 (9)	0.0116 (9)
C19	0.0259 (11)	0.0465 (14)	0.0495 (14)	0.0193 (11)	0.0167 (11)	0.0254 (12)
C20	0.0182 (10)	0.0450 (14)	0.0424 (13)	0.0069 (10)	0.0018 (9)	0.0274 (11)
C21	0.0298 (12)	0.0333 (12)	0.0255 (11)	0.0041 (10)	0.0001 (9)	0.0134 (9)
C22	0.0256 (10)	0.0277 (11)	0.0254 (10)	0.0092 (9)	0.0071 (8)	0.0110 (9)
O1	0.0372 (9)	0.0465 (10)	0.0370 (9)	0.0164 (8)	0.0067 (7)	0.0185 (8)
C23	0.0559 (16)	0.0368 (13)	0.0301 (12)	0.0170 (12)	0.0140 (11)	0.0145 (10)
C24	0.0449 (14)	0.0412 (14)	0.0350 (13)	0.0208 (12)	0.0062 (11)	0.0106 (11)
O2	0.0465 (10)	0.0412 (10)	0.0627 (12)	0.0218 (9)	0.0329 (9)	0.0252 (9)
C25	0.0296 (12)	0.0583 (17)	0.0482 (15)	0.0101 (12)	0.0137 (11)	0.0212 (13)
C26	0.0595 (18)	0.0364 (14)	0.0672 (19)	0.0201 (13)	0.0383 (16)	0.0188 (13)
O3	0.0635 (8)	0.0611 (8)	0.0590 (8)	0.0356 (6)	0.0160 (6)	0.0219 (6)
C27A	0.0561 (9)	0.0546 (9)	0.0546 (9)	0.0271 (7)	0.0179 (7)	0.0225 (7)
C28A	0.0508 (10)	0.0514 (10)	0.0503 (10)	0.0242 (8)	0.0202 (7)	0.0213 (8)
C27B	0.0561 (9)	0.0546 (9)	0.0546 (9)	0.0271 (7)	0.0179 (7)	0.0225 (7)
C28B	0.0508 (10)	0.0514 (10)	0.0503 (10)	0.0242 (8)	0.0202 (7)	0.0213 (8)
C27C	0.0561 (9)	0.0546 (9)	0.0546 (9)	0.0271 (7)	0.0179 (7)	0.0225 (7)
C28C	0.0508 (10)	0.0514 (10)	0.0503 (10)	0.0242 (8)	0.0202 (7)	0.0213 (8)

Zn—N2	2.0421 (16)	C21—C22	1.389 (2)
Zn—N1	2.0524 (16)	C21—H21	0.9300
N1—C1	1.372 (2)	C22—H22	0.9300
N1—C4	1.374 (2)	O1—C28Aii	1.397 (6)
N2—C9	1.371 (2)	O1—C23	1.4185
N2—C6	1.372 (2)	O1—C28Bii	1.487 (13)
C1—C10	1.405 (3)	O1—C28Cii	1.587 (12)
C1—C2	1.443 (3)	C23—C24	1.496 (3)
C2—C3	1.347 (3)	C23—H23A	0.9700
C2—H2	0.9300	C23—H23B	0.9700
C3—C4	1.443 (3)	C24—O2	1.400 (3)
C3—H3	0.9300	C24—H24A	0.9700
C4—C5	1.402 (3)	C24—H24B	0.9700
C5—C6	1.400 (3)	O2—C25	1.417 (3)
C5—C11	1.504 (3)	C25—C26	1.492 (4)
C6—C7	1.439 (3)	C25—H25A	0.9700
C7—C8	1.346 (3)	C25—H25B	0.9700
C7—H7	0.9300	C26—O3	1.384 (4)
C8—C9	1.445 (3)	C26—H26A	0.9700
C8—H8	0.9300	C26—H26B	0.9700
C9—C10i	1.406 (3)	O3—C27C	1.513 (12)
C10—C9i	1.406 (3)	O3—C27B	1.513 (13)
C10—C17	1.493 (3)	O3—C27A	1.517 (6)
C11—C16	1.379 (3)	C27A—C28A	1.504 (9)
C11—C12	1.384 (3)	C27A—H27A	0.9700
C12—C13	1.388 (3)	C27A—H27B	0.9700
C12—H12	0.9300	C28A—O1ii	1.397 (6)
C13—C14	1.370 (3)	C28A—H28A	0.9700
C13—H13	0.9300	C28A—H28B	0.9700
C14—C15	1.380 (3)	C27B—C28B	1.403 (18)
C14—H14	0.9300	C27B—H27C	0.9700
C15—C16	1.386 (3)	C27B—H27D	0.9700
C15—H15	0.9300	C28B—O1ii	1.487 (12)
C16—H16	0.9300	C28B—H28C	0.9700
C17—C22	1.392 (2)	C28B—H28D	0.9700
C17—C18	1.393 (3)	C27C—C28C	1.502 (18)
C18—C19	1.382 (3)	C27C—H27E	0.9700
C18—H18	0.9300	C27C—H27F	0.9700
C19—C20	1.383 (4)	C28C—O1ii	1.587 (12)
C19—H19	0.9300	C28C—H28E	0.9700
C20—C21	1.381 (4)	C28C—H28F	0.9700
C20—H20	0.9300
N2—Zn—N2i	180.0	C20—C21—H21	120.0
N2—Zn—N1i	89.28 (6)	C22—C21—H21	120.0
N2i—Zn—N1i	90.72 (6)	C21—C22—C17	120.83 (16)
N2—Zn—N1	90.72 (6)	C21—C22—H22	119.6
N2i—Zn—N1	89.28 (6)	C17—C22—H22	119.6
N1i—Zn—N1	180.0	C28Aii—O1—C23	121.4 (3)
C1—N1—C4	106.75 (16)	C23—O1—C28Bii	115.6 (5)
C1—N1—Zn	127.32 (13)	C23—O1—C28Cii	99.7 (5)
C4—N1—Zn	125.65 (13)	O1—C23—C24	113.75 (11)
C9—N2—C6	106.67 (16)	O1—C23—H23A	108.8
C9—N2—Zn	127.28 (13)	C24—C23—H23A	108.8
C6—N2—Zn	125.51 (13)	O1—C23—H23B	108.8
N1—C1—C10	125.32 (18)	C24—C23—H23B	108.8
N1—C1—C2	109.25 (17)	H23A—C23—H23B	107.7
C10—C1—C2	125.37 (18)	O2—C24—C23	109.77 (19)
C3—C2—C1	107.45 (17)	O2—C24—H24A	109.7
C3—C2—H2	126.3	C23—C24—H24A	109.7
C1—C2—H2	126.3	O2—C24—H24B	109.7
C2—C3—C4	107.10 (17)	C23—C24—H24B	109.7
C2—C3—H3	126.5	H24A—C24—H24B	108.2
C4—C3—H3	126.5	C24—O2—C25	114.6 (2)
N1—C4—C5	125.70 (17)	O2—C25—C26	108.3 (2)
N1—C4—C3	109.43 (17)	O2—C25—H25A	110.0
C5—C4—C3	124.81 (18)	C26—C25—H25A	110.0
C6—C5—C4	125.74 (18)	O2—C25—H25B	110.0
C6—C5—C11	116.99 (17)	C26—C25—H25B	110.0
C4—C5—C11	117.24 (17)	H25A—C25—H25B	108.4
N2—C6—C5	126.10 (18)	O3—C26—C25	108.8 (2)
N2—C6—C7	109.46 (17)	O3—C26—H26A	109.9
C5—C6—C7	124.44 (18)	C25—C26—H26A	109.9
C8—C7—C6	107.41 (18)	O3—C26—H26B	109.9
C8—C7—H7	126.3	C25—C26—H26B	109.9
C6—C7—H7	126.3	H26A—C26—H26B	108.3
C7—C8—C9	107.03 (18)	C26—O3—C27C	91.8 (5)
C7—C8—H8	126.5	C26—O3—C27B	109.8 (6)
C9—C8—H8	126.5	C26—O3—C27A	121.5 (3)
N2—C9—C10i	125.72 (18)	C28A—C27A—O3	103.6 (5)
N2—C9—C8	109.42 (17)	C28A—C27A—H27A	111.0
C10i—C9—C8	124.69 (18)	O3—C27A—H27A	111.0
C1—C10—C9i	124.99 (18)	C28A—C27A—H27B	111.0
C1—C10—C17	117.65 (17)	O3—C27A—H27B	111.0
C9i—C10—C17	117.36 (18)	H27A—C27A—H27B	109.0
C16—C11—C12	118.84 (19)	O1ii—C28A—C27A	109.5 (5)
C16—C11—C5	120.98 (18)	O1ii—C28A—H28A	109.8
C12—C11—C5	120.17 (18)	C27A—C28A—H28A	109.8
C11—C12—C13	120.5 (2)	O1ii—C28A—H28B	109.8
C11—C12—H12	119.8	C27A—C28A—H28B	109.8
C13—C12—H12	119.8	H28A—C28A—H28B	108.2
C14—C13—C12	120.3 (2)	C28B—C27B—O3	102.5 (10)
C14—C13—H13	119.8	C28B—C27B—H27C	111.3
C12—C13—H13	119.8	O3—C27B—H27C	111.3
C13—C14—C15	119.6 (2)	C28B—C27B—H27D	111.3
C13—C14—H14	120.2	O3—C27B—H27D	111.3
C15—C14—H14	120.2	H27C—C27B—H27D	109.2
C14—C15—C16	120.2 (2)	C27B—C28B—O1ii	108.4 (10)
C14—C15—H15	119.9	C27B—C28B—H28C	110.0
C16—C15—H15	119.9	O1ii—C28B—H28C	110.0
C11—C16—C15	120.6 (2)	C27B—C28B—H28D	110.0
C11—C16—H16	119.7	O1ii—C28B—H28D	110.0
C15—C16—H16	119.7	H28C—C28B—H28D	108.4
C22—C17—C18	118.35 (17)	C28C—C27C—O3	96.2 (9)
C22—C17—C10	121.02 (17)	C28C—C27C—H27E	112.5
C18—C17—C10	120.63 (18)	O3—C27C—H27E	112.5
C19—C18—C17	120.8 (2)	C28C—C27C—H27F	112.5
C19—C18—H18	119.6	O3—C27C—H27F	112.5
C17—C18—H18	119.6	H27E—C27C—H27F	110.0
C18—C19—C20	120.3 (2)	C27C—C28C—O1ii	100.7 (9)
C18—C19—H19	119.9	C27C—C28C—H28E	111.6
C20—C19—H19	119.9	O1ii—C28C—H28E	111.6
C21—C20—C19	119.7 (2)	C27C—C28C—H28F	111.6
C21—C20—H20	120.1	O1ii—C28C—H28F	111.6
C19—C20—H20	120.1	H28E—C28C—H28F	109.4
C20—C21—C22	120.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Cg1iii	0.93	2.98	3.824 (2)	152
C20—H20···Cg3iv	0.93	2.84	3.746 (2)	164
C24—H24A···Cg2	0.97	2.73	3.686 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N1/C1–C4, N2/C6–C9 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯Cg1i	0.93	2.98	3.824 (2)	152
C20—H20⋯Cg3ii	0.93	2.84	3.746 (2)	164
C24—H24A⋯Cg2	0.97	2.73	3.686 (3)	167

Symmetry codes: (i) ; (ii) .