9-(2,6-Dimethyl-phen-oxy-carbon-yl)-10-methyl-acridinium trifluoro-methane-sulfonate.

In the crystal structure of the title compound, C(23)H(20)NO(2) (+)·CF(3)SO(3) (-), adjacent cations are linked through a network of C-H⋯π and π-π inter-actions, and neighboring cations and anions via C-H⋯O inter-actions. The acridine and benzene ring systems are oriented at a dihedral angle of 31.4 (1)°. The carboxyl group is twisted at an angle of 66.3 (1)° relative to the acridine skeleton. The mean planes of the adjacent acridine moieties are parallel in the crystal structure.

Related literature

For general background to the chemiluminogenic properties of 9-phen­oxy­carbonyl-10-methyl­acridinium trifluoro­meth­ane­sulfonates, see: Brown et al. (2009 ▶); Natrajan et al. (2010 ▶). For related structures, see: Krzymiński et al. (2009 ▶); Niziołek et al. (2009 ▶). For inter­molecular inter­actions, see: Dorn et al. (2005 ▶); Hunter et al. (2001 ▶); Novoa et al. (2006 ▶); Takahashi et al. (2001 ▶). For the synthesis, see: Sato (1996 ▶); Niziołek et al. (2009 ▶).

Experimental

Crystal data

C23H20NO2 +·CF3SO3 −

M = 491.48

Triclinic,

a = 9.5841 (4) Å

b = 11.2491 (6) Å

c = 12.1738 (3) Å

α = 106.080 (3)°

β = 101.890 (3)°

γ = 110.755 (4)°

V = 1109.66 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 295 K

0.58 × 0.18 × 0.05 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

9670 measured reflections

3922 independent reflections

3124 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.125

S = 1.09

3922 reflections

321 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041449/ng5042sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041449/ng5042Isup2.hkl

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

C23H20NO2+·CF3SO3−	Z = 2
Mr = 491.48	F(000) = 508
Triclinic, P1	Dx = 1.471 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5841 (4) Å	Cell parameters from 66666 reflections
b = 11.2491 (6) Å	θ = 3.0–29.1°
c = 12.1738 (3) Å	µ = 0.21 mm−1
α = 106.080 (3)°	T = 295 K
β = 101.890 (3)°	Prism, light-yellow
γ = 110.755 (4)°	0.58 × 0.18 × 0.05 mm
V = 1109.66 (8) Å3

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	3124 reflections with I > 2σ(I)
Radiation source: Enhanced (Mo) X-ray Source	Rint = 0.016
graphite	θmax = 25.1°, θmin = 3.1°
Detector resolution: 10.4002 pixels mm-1	h = −11→11
ω scans	k = −13→10
9670 measured reflections	l = −14→14
3922 independent 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0673P)2 + 0.2264P] where P = (Fo2 + 2Fc2)/3
3922 reflections	(Δ/σ)max = 0.001
321 parameters	Δρmax = 0.33 e Å−3
6 restraints	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.3818 (3)	0.3638 (2)	0.13066 (19)	0.0649 (6)
H1	0.4654	0.3528	0.1091	0.078*
C2	0.2838 (3)	0.3952 (3)	0.0588 (2)	0.0777 (7)
H2	0.2996	0.4048	−0.0118	0.093*
C3	0.1595 (3)	0.4130 (3)	0.0913 (2)	0.0787 (8)
H3	0.0932	0.4350	0.0419	0.094*
C4	0.1322 (3)	0.3992 (2)	0.1928 (2)	0.0687 (6)
H4	0.0489	0.4130	0.2125	0.082*
C5	0.2865 (2)	0.3196 (2)	0.56175 (19)	0.0545 (5)
H5	0.1991	0.3261	0.5797	0.065*
C6	0.3931 (3)	0.3026 (2)	0.6409 (2)	0.0592 (5)
H6	0.3771	0.2975	0.7126	0.071*
C7	0.5267 (2)	0.2924 (2)	0.61744 (18)	0.0557 (5)
H7	0.5987	0.2820	0.6737	0.067*
C8	0.5505 (2)	0.29779 (19)	0.51298 (17)	0.0479 (4)
H8	0.6386	0.2898	0.4975	0.057*
C9	0.46128 (19)	0.32004 (18)	0.31651 (16)	0.0424 (4)
N10	0.20515 (16)	0.34795 (16)	0.37176 (15)	0.0499 (4)
C11	0.3594 (2)	0.34746 (19)	0.23794 (16)	0.0474 (4)
C12	0.2299 (2)	0.36386 (19)	0.26929 (17)	0.0505 (5)
C13	0.44292 (19)	0.31544 (17)	0.42602 (15)	0.0411 (4)
C14	0.30806 (19)	0.32732 (18)	0.45257 (17)	0.0448 (4)
C15	0.5963 (2)	0.29831 (19)	0.28346 (16)	0.0436 (4)
O16	0.53926 (14)	0.18238 (13)	0.18486 (11)	0.0503 (3)
O17	0.73309 (15)	0.37184 (15)	0.33881 (13)	0.0625 (4)
C18	0.6473 (2)	0.1321 (2)	0.15004 (17)	0.0514 (5)
C19	0.6730 (3)	0.0416 (2)	0.1981 (2)	0.0641 (6)
C20	0.7664 (3)	−0.0180 (3)	0.1546 (3)	0.0849 (8)
H20	0.7870	−0.0800	0.1844	0.102*
C21	0.8276 (3)	0.0133 (3)	0.0693 (3)	0.0922 (9)
H21	0.8888	−0.0280	0.0412	0.111*
C22	0.8000 (3)	0.1047 (3)	0.0246 (2)	0.0813 (8)
H22	0.8428	0.1245	−0.0338	0.098*
C23	0.7089 (2)	0.1689 (2)	0.06460 (19)	0.0631 (6)
C24	0.6045 (4)	0.0075 (3)	0.2916 (3)	0.0923 (9)
H24A	0.4922	−0.0213	0.2627	0.138*
H24B	0.6527	0.0874	0.3658	0.138*
H24C	0.6248	−0.0654	0.3061	0.138*
C25	0.6814 (3)	0.2718 (3)	0.0184 (2)	0.0835 (8)
H25A	0.5697	0.2402	−0.0195	0.125*
H25B	0.7338	0.2826	−0.0399	0.125*
H25C	0.7232	0.3586	0.0850	0.125*
C26	0.0613 (3)	0.3550 (3)	0.3959 (3)	0.0779 (8)
H26A	−0.027 (3)	0.305 (3)	0.3197 (17)	0.113 (10)*
H26B	0.034 (3)	0.307 (3)	0.448 (2)	0.106 (11)*
H26C	0.069 (5)	0.4454 (19)	0.431 (3)	0.184 (19)*
S27	0.95913 (6)	0.27457 (6)	0.72251 (5)	0.05989 (19)
O28	1.1219 (2)	0.3034 (3)	0.77069 (16)	0.1008 (7)
O29	0.9225 (2)	0.3134 (2)	0.62202 (16)	0.0875 (5)
O30	0.8851 (2)	0.3042 (2)	0.81008 (15)	0.0879 (6)
C31	0.8618 (4)	0.0892 (3)	0.6536 (3)	0.0856 (8)
F32	0.8764 (3)	0.0335 (2)	0.7353 (3)	0.1501 (9)
F33	0.9169 (3)	0.0417 (2)	0.5713 (2)	0.1554 (10)
F34	0.7072 (2)	0.0441 (2)	0.5986 (2)	0.1331 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0770 (14)	0.0765 (15)	0.0556 (12)	0.0464 (13)	0.0212 (10)	0.0297 (11)
C2	0.1007 (19)	0.0832 (18)	0.0582 (13)	0.0549 (16)	0.0142 (13)	0.0298 (12)
C3	0.0827 (17)	0.0773 (17)	0.0680 (15)	0.0458 (14)	−0.0039 (13)	0.0235 (13)
C4	0.0540 (12)	0.0665 (14)	0.0776 (15)	0.0362 (11)	0.0030 (11)	0.0176 (12)
C5	0.0524 (11)	0.0474 (11)	0.0663 (12)	0.0206 (9)	0.0297 (10)	0.0199 (9)
C6	0.0715 (13)	0.0539 (12)	0.0596 (11)	0.0266 (10)	0.0331 (10)	0.0252 (10)
C7	0.0611 (12)	0.0542 (12)	0.0549 (11)	0.0254 (10)	0.0182 (9)	0.0261 (9)
C8	0.0437 (9)	0.0490 (11)	0.0550 (10)	0.0226 (8)	0.0171 (8)	0.0220 (9)
C9	0.0369 (8)	0.0385 (9)	0.0483 (9)	0.0161 (7)	0.0119 (7)	0.0140 (8)
N10	0.0350 (7)	0.0455 (9)	0.0609 (9)	0.0192 (7)	0.0114 (7)	0.0099 (7)
C11	0.0448 (9)	0.0433 (10)	0.0497 (10)	0.0214 (8)	0.0091 (8)	0.0139 (8)
C12	0.0421 (9)	0.0422 (10)	0.0541 (11)	0.0186 (8)	0.0046 (8)	0.0084 (8)
C13	0.0355 (8)	0.0346 (9)	0.0484 (9)	0.0134 (7)	0.0128 (7)	0.0130 (7)
C14	0.0373 (9)	0.0344 (9)	0.0546 (10)	0.0125 (7)	0.0149 (8)	0.0105 (8)
C15	0.0425 (10)	0.0471 (10)	0.0475 (9)	0.0223 (8)	0.0170 (8)	0.0222 (8)
O16	0.0422 (6)	0.0538 (8)	0.0512 (7)	0.0208 (6)	0.0188 (5)	0.0130 (6)
O17	0.0392 (7)	0.0589 (9)	0.0731 (9)	0.0175 (6)	0.0162 (6)	0.0095 (7)
C18	0.0414 (9)	0.0491 (11)	0.0562 (11)	0.0166 (8)	0.0223 (8)	0.0097 (9)
C19	0.0627 (12)	0.0548 (13)	0.0801 (14)	0.0277 (11)	0.0356 (11)	0.0225 (11)
C20	0.0797 (16)	0.0653 (16)	0.122 (2)	0.0416 (14)	0.0483 (16)	0.0305 (15)
C21	0.0762 (16)	0.0717 (17)	0.129 (2)	0.0345 (14)	0.0622 (17)	0.0164 (17)
C22	0.0696 (15)	0.0780 (18)	0.0849 (16)	0.0207 (13)	0.0505 (13)	0.0128 (14)
C23	0.0526 (11)	0.0643 (14)	0.0577 (11)	0.0143 (10)	0.0260 (9)	0.0121 (10)
C24	0.125 (2)	0.0864 (19)	0.118 (2)	0.0658 (18)	0.0734 (19)	0.0631 (17)
C25	0.0869 (17)	0.106 (2)	0.0748 (15)	0.0398 (16)	0.0463 (13)	0.0480 (15)
C26	0.0458 (12)	0.101 (2)	0.0848 (17)	0.0402 (13)	0.0235 (12)	0.0217 (16)
S27	0.0655 (3)	0.0737 (4)	0.0501 (3)	0.0355 (3)	0.0266 (2)	0.0255 (3)
O28	0.0647 (10)	0.1509 (19)	0.0711 (11)	0.0372 (11)	0.0187 (8)	0.0367 (12)
O29	0.1033 (13)	0.1112 (14)	0.0781 (11)	0.0551 (12)	0.0399 (10)	0.0610 (11)
O30	0.1185 (15)	0.1062 (14)	0.0730 (10)	0.0705 (12)	0.0590 (10)	0.0348 (10)
C31	0.101 (2)	0.091 (2)	0.0888 (18)	0.0516 (17)	0.0548 (16)	0.0386 (16)
F32	0.212 (3)	0.1266 (17)	0.191 (2)	0.1025 (18)	0.106 (2)	0.1062 (17)
F33	0.187 (2)	0.1174 (16)	0.164 (2)	0.0741 (16)	0.1115 (18)	0.0081 (14)
F34	0.0897 (13)	0.1208 (16)	0.1312 (15)	0.0049 (11)	0.0360 (11)	0.0222 (12)

C1—C2	1.357 (3)	O16—C18	1.426 (2)
C1—C11	1.417 (3)	C18—C19	1.374 (3)
C1—H1	0.9300	C18—C23	1.385 (3)
C2—C3	1.392 (4)	C19—C20	1.398 (3)
C2—H2	0.9300	C19—C24	1.498 (3)
C3—C4	1.352 (4)	C20—C21	1.361 (4)
C3—H3	0.9300	C20—H20	0.9300
C4—C12	1.419 (3)	C21—C22	1.366 (4)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.357 (3)	C22—C23	1.396 (3)
C5—C14	1.408 (3)	C22—H22	0.9300
C5—H5	0.9300	C23—C25	1.497 (4)
C6—C7	1.404 (3)	C24—H24A	0.9600
C6—H6	0.9300	C24—H24B	0.9600
C7—C8	1.351 (3)	C24—H24C	0.9600
C7—H7	0.9300	C25—H25A	0.9600
C8—C13	1.427 (3)	C25—H25B	0.9600
C8—H8	0.9300	C25—H25C	0.9600
C9—C13	1.393 (3)	C26—H26A	0.971 (16)
C9—C11	1.398 (3)	C26—H26B	0.966 (16)
C9—C15	1.510 (2)	C26—H26C	0.956 (17)
N10—C12	1.364 (3)	S27—O30	1.4262 (17)
N10—C14	1.372 (2)	S27—O29	1.4274 (17)
N10—C26	1.492 (3)	S27—O28	1.4290 (19)
C11—C12	1.428 (3)	S27—C31	1.803 (3)
C13—C14	1.436 (2)	C31—F33	1.301 (3)
C15—O17	1.190 (2)	C31—F32	1.323 (4)
C15—O16	1.341 (2)	C31—F34	1.331 (3)
C2—C1—C11	121.3 (2)	C19—C18—O16	116.51 (17)
C2—C1—H1	119.3	C23—C18—O16	118.52 (19)
C11—C1—H1	119.3	C18—C19—C20	116.4 (2)
C1—C2—C3	119.5 (2)	C18—C19—C24	122.2 (2)
C1—C2—H2	120.3	C20—C19—C24	121.5 (2)
C3—C2—H2	120.3	C21—C20—C19	121.0 (3)
C4—C3—C2	122.0 (2)	C21—C20—H20	119.5
C4—C3—H3	119.0	C19—C20—H20	119.5
C2—C3—H3	119.0	C20—C21—C22	120.7 (2)
C3—C4—C12	120.4 (2)	C20—C21—H21	119.6
C3—C4—H4	119.8	C22—C21—H21	119.6
C12—C4—H4	119.8	C21—C22—C23	121.3 (2)
C6—C5—C14	120.13 (18)	C21—C22—H22	119.3
C6—C5—H5	119.9	C23—C22—H22	119.3
C14—C5—H5	119.9	C18—C23—C22	115.8 (2)
C5—C6—C7	121.8 (2)	C18—C23—C25	122.5 (2)
C5—C6—H6	119.1	C22—C23—C25	121.7 (2)
C7—C6—H6	119.1	C19—C24—H24A	109.5
C8—C7—C6	119.85 (19)	C19—C24—H24B	109.5
C8—C7—H7	120.1	H24A—C24—H24B	109.5
C6—C7—H7	120.1	C19—C24—H24C	109.5
C7—C8—C13	121.10 (18)	H24A—C24—H24C	109.5
C7—C8—H8	119.4	H24B—C24—H24C	109.5
C13—C8—H8	119.4	C23—C25—H25A	109.5
C13—C9—C11	121.32 (16)	C23—C25—H25B	109.5
C13—C9—C15	119.28 (15)	H25A—C25—H25B	109.5
C11—C9—C15	119.39 (17)	C23—C25—H25C	109.5
C12—N10—C14	122.34 (15)	H25A—C25—H25C	109.5
C12—N10—C26	118.00 (18)	H25B—C25—H25C	109.5
C14—N10—C26	119.65 (19)	N10—C26—H26A	108.1 (18)
C9—C11—C1	122.93 (18)	N10—C26—H26B	109.5 (19)
C9—C11—C12	118.46 (18)	H26A—C26—H26B	106.0 (18)
C1—C11—C12	118.58 (18)	N10—C26—H26C	116 (3)
N10—C12—C4	122.02 (19)	H26A—C26—H26C	109 (2)
N10—C12—C11	119.78 (17)	H26B—C26—H26C	108 (2)
C4—C12—C11	118.2 (2)	O30—S27—O29	115.49 (12)
C9—C13—C8	123.28 (16)	O30—S27—O28	115.69 (11)
C9—C13—C14	118.62 (16)	O29—S27—O28	114.61 (12)
C8—C13—C14	118.10 (17)	O30—S27—C31	102.71 (12)
N10—C14—C5	121.83 (17)	O29—S27—C31	102.86 (13)
N10—C14—C13	119.14 (17)	O28—S27—C31	102.72 (15)
C5—C14—C13	119.02 (17)	F33—C31—F32	108.6 (3)
O17—C15—O16	125.17 (17)	F33—C31—F34	106.8 (3)
O17—C15—C9	124.77 (17)	F32—C31—F34	106.9 (3)
O16—C15—C9	110.03 (14)	F33—C31—S27	111.8 (2)
C15—O16—C18	118.64 (14)	F32—C31—S27	111.7 (2)
C19—C18—C23	124.78 (19)	F34—C31—S27	110.7 (2)
C11—C1—C2—C3	0.6 (4)	C8—C13—C14—N10	178.32 (15)
C1—C2—C3—C4	−0.4 (4)	C9—C13—C14—C5	178.53 (16)
C2—C3—C4—C12	−0.9 (4)	C8—C13—C14—C5	−0.7 (2)
C14—C5—C6—C7	0.1 (3)	C13—C9—C15—O17	−63.4 (3)
C5—C6—C7—C8	−0.9 (3)	C11—C9—C15—O17	115.1 (2)
C6—C7—C8—C13	0.8 (3)	C13—C9—C15—O16	114.90 (17)
C13—C9—C11—C1	174.81 (18)	C11—C9—C15—O16	−66.6 (2)
C15—C9—C11—C1	−3.7 (3)	O17—C15—O16—C18	7.9 (3)
C13—C9—C11—C12	−3.2 (3)	C9—C15—O16—C18	−170.39 (16)
C15—C9—C11—C12	178.28 (16)	C15—O16—C18—C19	90.5 (2)
C2—C1—C11—C9	−177.6 (2)	C15—O16—C18—C23	−94.2 (2)
C2—C1—C11—C12	0.4 (3)	C23—C18—C19—C20	−1.1 (3)
C14—N10—C12—C4	−173.36 (18)	O16—C18—C19—C20	173.85 (19)
C26—N10—C12—C4	6.0 (3)	C23—C18—C19—C24	179.2 (2)
C14—N10—C12—C11	5.4 (3)	O16—C18—C19—C24	−5.9 (3)
C26—N10—C12—C11	−175.25 (19)	C18—C19—C20—C21	0.0 (4)
C3—C4—C12—N10	−179.4 (2)	C24—C19—C20—C21	179.8 (3)
C3—C4—C12—C11	1.8 (3)	C19—C20—C21—C22	0.4 (4)
C9—C11—C12—N10	−2.2 (3)	C20—C21—C22—C23	0.1 (4)
C1—C11—C12—N10	179.66 (17)	C19—C18—C23—C22	1.5 (3)
C9—C11—C12—C4	176.56 (17)	O16—C18—C23—C22	−173.29 (17)
C1—C11—C12—C4	−1.5 (3)	C19—C18—C23—C25	−177.9 (2)
C11—C9—C13—C8	−175.30 (17)	O16—C18—C23—C25	7.3 (3)
C15—C9—C13—C8	3.2 (3)	C21—C22—C23—C18	−1.0 (4)
C11—C9—C13—C14	5.5 (3)	C21—C22—C23—C25	178.4 (2)
C15—C9—C13—C14	−175.99 (15)	O30—S27—C31—F33	−178.7 (2)
C7—C8—C13—C9	−179.25 (18)	O29—S27—C31—F33	61.1 (3)
C7—C8—C13—C14	0.0 (3)	O28—S27—C31—F33	−58.3 (3)
C12—N10—C14—C5	175.98 (17)	O30—S27—C31—F32	−56.7 (2)
C26—N10—C14—C5	−3.4 (3)	O29—S27—C31—F32	−177.0 (2)
C12—N10—C14—C13	−3.0 (3)	O28—S27—C31—F32	63.7 (2)
C26—N10—C14—C13	177.62 (19)	O30—S27—C31—F34	62.4 (2)
C6—C5—C14—N10	−178.31 (18)	O29—S27—C31—F34	−57.9 (2)
C6—C5—C14—C13	0.7 (3)	O28—S27—C31—F34	−177.18 (19)
C9—C13—C14—N10	−2.4 (2)

Cg4 is the centroid of the C18–C23 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O28i	0.93	2.51	3.224 (3)	134
C25—H25B···O30ii	0.96	2.57	3.525 (3)	176
C26—H26A···Cg4iii	0.96 (3)	2.86 (2)	3.774 (3)	158 (3)
C26—H26B···O29iii	0.96 (3)	2.56 (3)	3.369 (4)	142 (2)

X	I	J	I···J	X···J	X–I···J
C31	F32	Cg1iv	3.655 (3)	4.490 (4)	121.5 (2)
C31	F32	Cg3iv	3.886 (3)	3.974 (4)	84.1 (2)
C31	F33	Cg3iv	3.746 (3)	3.974 (4)	90.4 (2)
C31	F34	Cg3iv	3.481 (2)	3.974 (4)	101.9 (2)

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgI_Offset
1	3v	3.502 (2)	2.71 (10)	3.473 (1)	0.445 (1)
2	3v	3.977 (2)	6.38 (11)	3.286 (1)	2.240 (1)
3	1v	3.502 (2)	2.71 (10)	3.470 (1)	0.480 (1)
3	2v	3.977 (2)	6.38 (11)	3.503 (1)	1.883 (1)

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O28i	0.93	2.51	3.224 (3)	134
C25—H25B⋯O30ii	0.96	2.57	3.525 (3)	176
C26—H26A⋯Cg4iii	0.96 (3)	2.86 (2)	3.774 (3)	158 (3)
C26—H26B⋯O29iii	0.96 (3)	2.56 (3)	3.369 (4)	142 (2)

Symmetry codes: (i) ; (ii) ; (iii) .

Table 2

π–π inter­actions (Å,°)

Cg1, Cg2 and Cg3 are the centroids of the C9/N10/C11–C14, C1–C4/C11/C12 and C5–C8/C13/C14 rings, respectively. CgI⋯CgJ is the distance between ring centroids. The dihedral angle is that between the planes of the rings I and J. CgI_Perp is the perpendicular distance of CgI from ring J. CgI_Offset is the distance between CgI and perpendicular projection of CgJ on ring I.

I	J	CgI⋯CgJ	Dihedral angle	CgI_Perp	CgI_Offset
1	3v	3.502 (2)	2.71 (10)	3.473 (1)	0.445 (1)
2	3v	3.977 (2)	6.38 (11)	3.286 (1)	2.240 (1)
3	1v	3.502 (2)	2.71 (10)	3.470 (1)	0.480 (1)
3	2v	3.977 (2)	6.38 (11)	3.503 (1)	1.883 (1)

Symmetry code: (v) .