2-(2,4-Dichloro-phen-yl)-9-phenyl-2,3-di-hydro-thieno[3,2-b]quinoline.

In the title compound, C(23)H(15)Cl(2)NS, the quinoline system is almost planar [r.m.s. deviation = 0.013 (2) Å]. The phenyl group is disordered over two positions with site occupancies of 0.55 and 0.45, and is oriented in a nearly perpendicular configuration to the quinoline ring [the dihedral angles between the quinoline ring and the major and minor disordered components of the phenyl ring are 81.8 (2) and 71.6 (2)°, respectively]. The dihydro-thiene ring adopts an envelope conformation. The dihedral angle between the chloro-phenyl ring and the quinoline system is 79.32 (1)°. In the crystal weak C-H⋯π inter-actions occur.

Related literature

For the biological activity of quinoline derivatives, see: Kalluraya & Sreenivasa (1998 ▶); Maguire et al. (1994 ▶); Doube et al. (1998 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C23H15Cl2NS

M = 408.32

Monoclinic,

a = 11.8860 (5) Å

b = 11.5040 (5) Å

c = 14.0270 (6) Å

β = 94.297 (9)°

V = 1912.61 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 293 K

0.19 × 0.16 × 0.11 mm

Data collection

Nonius MACH-3 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.917, T max = 0.951

3917 measured reflections

3363 independent reflections

2577 reflections with I > 2σ(I)

R int = 0.014

2 standard reflections frequency: 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.091

S = 1.02

3363 reflections

284 parameters

18 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025380/at2782sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025380/at2782Isup2.hkl

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

C23H15Cl2NS	F(000) = 840
Mr = 408.32	Dx = 1.418 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.8860 (5) Å	θ = 2–25°
b = 11.5040 (5) Å	µ = 0.46 mm−1
c = 14.0270 (6) Å	T = 293 K
β = 94.297 (9)°	Block, colourless
V = 1912.61 (14) Å3	0.19 × 0.16 × 0.11 mm
Z = 4

Nonius MACH-3 diffractometer	2577 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
graphite	θmax = 25.0°, θmin = 2.3°
ω–2θ scans	h = 0→14
Absorption correction: ψ scan (North et al., 1968)	k = −1→13
Tmin = 0.917, Tmax = 0.951	l = −16→16
3917 measured reflections	2 standard reflections every 60 min
3363 independent reflections	intensity decay: none

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0458P)2 + 0.5943P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3363 reflections	Δρmax = 0.20 e Å−3
284 parameters	Δρmin = −0.22 e Å−3
18 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (10)

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	Occ. (<1)
C2	0.11979 (16)	0.26004 (19)	0.25210 (14)	0.0464 (5)
C3	0.14508 (15)	0.30797 (18)	0.34454 (13)	0.0428 (4)
C4	0.21084 (15)	0.41146 (17)	0.35382 (12)	0.0405 (4)
C5	0.24702 (14)	0.45739 (17)	0.27087 (12)	0.0395 (4)
C6	0.21560 (15)	0.40461 (18)	0.18138 (12)	0.0428 (4)
C7	0.05703 (19)	0.1566 (2)	0.24282 (17)	0.0629 (6)
H7	0.0407	0.1247	0.1825	0.075*
C8	0.01978 (19)	0.1025 (2)	0.3209 (2)	0.0701 (7)
H8	−0.0219	0.0343	0.3134	0.084*
C9	0.04406 (18)	0.1493 (2)	0.41213 (18)	0.0632 (6)
H9	0.0185	0.1117	0.4651	0.076*
C10	0.10473 (17)	0.2492 (2)	0.42434 (15)	0.0521 (5)
H10	0.1199	0.2793	0.4855	0.063*
C17	0.25242 (17)	0.4742 (2)	0.09826 (14)	0.0523 (5)
H17A	0.1912	0.5235	0.0727	0.063*
H17B	0.2735	0.4225	0.0479	0.063*
C18	0.35345 (17)	0.54856 (19)	0.13425 (13)	0.0478 (5)
H18	0.3512	0.6213	0.0977	0.057*
C19	0.46829 (16)	0.49449 (17)	0.12880 (12)	0.0446 (5)
C20	0.56613 (17)	0.55995 (18)	0.14608 (14)	0.0472 (5)
C21	0.67332 (18)	0.5143 (2)	0.14224 (14)	0.0528 (5)
H21	0.7369	0.5605	0.1549	0.063*
C22	0.68341 (19)	0.3986 (2)	0.11907 (14)	0.0553 (5)
C23	0.5893 (2)	0.3301 (2)	0.10080 (15)	0.0588 (6)
H23	0.5971	0.2523	0.0847	0.071*
C24	0.48327 (19)	0.37731 (19)	0.10646 (14)	0.0524 (5)
H24	0.4202	0.3300	0.0951	0.063*
N1	0.15524 (13)	0.31025 (16)	0.17022 (11)	0.0487 (4)
Cl1	0.55600 (5)	0.70657 (5)	0.17491 (5)	0.0697 (2)
Cl2	0.81734 (6)	0.33969 (7)	0.11513 (6)	0.0859 (3)
S1	0.32820 (5)	0.58301 (5)	0.26012 (4)	0.05025 (17)
C11	0.23924 (16)	0.46862 (18)	0.44796 (13)	0.0453 (5)
C14	0.2954 (3)	0.5830 (3)	0.61987 (18)	0.0854 (9)
H14	0.312 (2)	0.624 (3)	0.678 (2)	0.102*
C12	0.1794 (7)	0.5609 (6)	0.4804 (6)	0.067 (2)	0.55
H12	0.1176	0.5866	0.4415	0.080*	0.55
C13	0.2032 (7)	0.6189 (8)	0.5661 (6)	0.085 (3)	0.55
H13	0.1581	0.6792	0.5854	0.102*	0.55
C15	0.3566 (7)	0.4863 (7)	0.5933 (7)	0.094 (3)	0.55
H15	0.4163	0.4594	0.6340	0.112*	0.55
C16	0.3298 (6)	0.4293 (8)	0.5068 (6)	0.076 (3)	0.55
H16	0.3722	0.3660	0.4890	0.091*	0.55
C12'	0.1533 (9)	0.5268 (6)	0.4904 (7)	0.055 (2)	0.45
H12'	0.0794	0.5282	0.4637	0.066*	0.45
C13'	0.1868 (8)	0.5831 (8)	0.5765 (7)	0.075 (3)	0.45
H13'	0.1319	0.6236	0.6068	0.090*	0.45
C15'	0.3783 (9)	0.5283 (9)	0.5745 (8)	0.083 (3)	0.45
H15'	0.4527	0.5289	0.6004	0.099*	0.45
C16'	0.3486 (7)	0.4717 (9)	0.4887 (7)	0.064 (3)	0.45
H16'	0.4048	0.4344	0.4574	0.077*	0.45

	U11	U22	U33	U12	U13	U23
C2	0.0389 (10)	0.0567 (12)	0.0433 (10)	−0.0048 (9)	−0.0001 (8)	0.0028 (9)
C3	0.0359 (9)	0.0532 (12)	0.0393 (10)	0.0020 (9)	0.0028 (7)	0.0059 (9)
C4	0.0377 (9)	0.0506 (11)	0.0334 (9)	0.0059 (9)	0.0035 (7)	0.0029 (8)
C5	0.0373 (9)	0.0471 (10)	0.0340 (9)	0.0011 (8)	0.0030 (7)	0.0011 (8)
C6	0.0387 (9)	0.0563 (12)	0.0332 (9)	−0.0003 (9)	0.0017 (7)	0.0014 (9)
C7	0.0544 (13)	0.0730 (16)	0.0599 (13)	−0.0185 (12)	−0.0042 (10)	−0.0018 (12)
C8	0.0527 (13)	0.0715 (16)	0.0858 (18)	−0.0230 (12)	0.0033 (12)	0.0093 (14)
C9	0.0502 (12)	0.0736 (16)	0.0670 (15)	−0.0064 (12)	0.0114 (11)	0.0221 (12)
C10	0.0467 (11)	0.0646 (13)	0.0459 (11)	0.0017 (10)	0.0092 (9)	0.0101 (10)
C17	0.0532 (11)	0.0699 (14)	0.0339 (9)	−0.0036 (11)	0.0038 (8)	0.0064 (10)
C18	0.0537 (11)	0.0552 (12)	0.0353 (9)	−0.0033 (10)	0.0087 (8)	0.0079 (9)
C19	0.0540 (11)	0.0492 (11)	0.0314 (9)	−0.0030 (9)	0.0089 (8)	0.0074 (8)
C20	0.0554 (12)	0.0465 (11)	0.0410 (10)	−0.0023 (9)	0.0124 (9)	0.0054 (8)
C21	0.0524 (12)	0.0611 (14)	0.0461 (11)	−0.0019 (10)	0.0118 (9)	0.0094 (10)
C22	0.0631 (13)	0.0604 (14)	0.0443 (11)	0.0125 (11)	0.0168 (10)	0.0137 (10)
C23	0.0842 (17)	0.0479 (12)	0.0456 (11)	0.0063 (12)	0.0138 (11)	0.0070 (10)
C24	0.0649 (13)	0.0514 (12)	0.0416 (10)	−0.0075 (10)	0.0077 (9)	0.0049 (9)
N1	0.0466 (9)	0.0625 (11)	0.0364 (8)	−0.0067 (8)	−0.0004 (7)	−0.0022 (8)
Cl1	0.0660 (4)	0.0495 (3)	0.0953 (5)	−0.0083 (3)	0.0177 (3)	−0.0065 (3)
Cl2	0.0773 (4)	0.0853 (5)	0.0990 (5)	0.0299 (4)	0.0315 (4)	0.0238 (4)
S1	0.0578 (3)	0.0512 (3)	0.0430 (3)	−0.0080 (2)	0.0117 (2)	−0.0035 (2)
C11	0.0528 (11)	0.0530 (12)	0.0303 (9)	−0.0003 (10)	0.0046 (8)	0.0038 (9)
C14	0.132 (3)	0.085 (2)	0.0384 (13)	−0.019 (2)	0.0008 (16)	−0.0091 (14)
C12	0.086 (5)	0.047 (4)	0.064 (4)	0.013 (3)	−0.018 (3)	−0.007 (3)
C13	0.148 (7)	0.041 (5)	0.062 (5)	0.015 (4)	−0.022 (4)	−0.009 (3)
C15	0.076 (5)	0.158 (9)	0.043 (4)	0.005 (5)	−0.016 (3)	−0.007 (5)
C16	0.070 (4)	0.112 (7)	0.044 (3)	0.031 (4)	−0.003 (3)	−0.009 (4)
C12'	0.077 (5)	0.048 (5)	0.042 (3)	0.002 (4)	0.012 (3)	0.000 (3)
C13'	0.144 (8)	0.033 (5)	0.050 (4)	0.024 (4)	0.028 (5)	0.001 (3)
C15'	0.083 (5)	0.113 (7)	0.051 (6)	−0.027 (5)	−0.005 (4)	−0.012 (5)
C16'	0.060 (4)	0.088 (7)	0.044 (5)	−0.007 (4)	−0.001 (3)	−0.010 (4)

C2—N1	1.379 (2)	C21—C22	1.378 (3)
C2—C7	1.405 (3)	C21—H21	0.9300
C2—C3	1.420 (3)	C22—C23	1.376 (3)
C3—C10	1.421 (3)	C22—Cl2	1.735 (2)
C3—C4	1.425 (3)	C23—C24	1.380 (3)
C4—C5	1.376 (2)	C23—H23	0.9300
C4—C11	1.491 (3)	C24—H24	0.9300
C5—C6	1.419 (3)	C11—C12	1.374 (7)
C5—S1	1.7505 (19)	C11—C16'	1.381 (8)
C6—N1	1.304 (2)	C11—C16	1.383 (7)
C6—C17	1.506 (3)	C11—C12'	1.391 (8)
C7—C8	1.362 (3)	C14—C13	1.348 (7)
C7—H7	0.9300	C14—C15'	1.366 (8)
C8—C9	1.399 (4)	C14—C13'	1.385 (8)
C8—H8	0.9300	C14—C15	1.395 (7)
C9—C10	1.361 (3)	C14—H14	0.95 (3)
C9—H9	0.9300	C12—C13	1.385 (7)
C10—H10	0.9300	C12—H12	0.9300
C17—C18	1.529 (3)	C13—H13	0.9300
C17—H17A	0.9700	C15—C16	1.395 (7)
C17—H17B	0.9700	C15—H15	0.9300
C18—C19	1.507 (3)	C16—H16	0.9300
C18—S1	1.8557 (19)	C12'—C13'	1.401 (8)
C18—H18	0.9800	C12'—H12'	0.9300
C19—C20	1.391 (3)	C13'—H13'	0.9300
C19—C24	1.398 (3)	C15'—C16'	1.391 (8)
C20—C21	1.383 (3)	C15'—H15'	0.9300
C20—Cl1	1.741 (2)	C16'—H16'	0.9300
N1—C2—C7	118.08 (18)	C22—C23—H23	120.1
N1—C2—C3	122.72 (18)	C24—C23—H23	120.1
C7—C2—C3	119.20 (18)	C23—C24—C19	121.6 (2)
C2—C3—C10	118.26 (19)	C23—C24—H24	119.2
C2—C3—C4	119.01 (16)	C19—C24—H24	119.2
C10—C3—C4	122.72 (18)	C6—N1—C2	116.63 (16)
C5—C4—C3	116.60 (16)	C5—S1—C18	92.02 (9)
C5—C4—C11	121.01 (18)	C12—C11—C16'	109.8 (7)
C3—C4—C11	122.39 (16)	C12—C11—C16	117.0 (6)
C4—C5—C6	120.37 (18)	C16'—C11—C16	25.1 (5)
C4—C5—S1	126.81 (15)	C12—C11—C12'	21.9 (5)
C6—C5—S1	112.78 (13)	C16'—C11—C12'	120.6 (7)
N1—C6—C5	124.62 (17)	C16—C11—C12'	117.7 (6)
N1—C6—C17	122.59 (17)	C12—C11—C4	123.0 (4)
C5—C6—C17	112.65 (17)	C16'—C11—C4	121.4 (5)
C8—C7—C2	121.0 (2)	C16—C11—C4	119.9 (4)
C8—C7—H7	119.5	C12'—C11—C4	117.8 (5)
C2—C7—H7	119.5	C13—C14—C15'	117.7 (7)
C7—C8—C9	120.2 (2)	C13—C14—C13'	20.3 (6)
C7—C8—H8	119.9	C15'—C14—C13'	118.5 (7)
C9—C8—H8	119.9	C13—C14—C15	120.9 (6)
C10—C9—C8	120.7 (2)	C15'—C14—C15	25.8 (6)
C10—C9—H9	119.6	C13'—C14—C15	111.8 (6)
C8—C9—H9	119.6	C13—C14—H14	116.3 (19)
C9—C10—C3	120.6 (2)	C15'—C14—H14	120.9 (19)
C9—C10—H10	119.7	C13'—C14—H14	120.5 (19)
C3—C10—H10	119.7	C15—C14—H14	122.7 (19)
C6—C17—C18	107.96 (16)	C11—C12—C13	125.6 (8)
C6—C17—H17A	110.1	C11—C12—H12	117.2
C18—C17—H17A	110.1	C13—C12—H12	117.2
C6—C17—H17B	110.1	C14—C13—C12	116.3 (8)
C18—C17—H17B	110.1	C14—C13—H13	121.9
H17A—C17—H17B	108.4	C12—C13—H13	121.9
C19—C18—C17	116.36 (18)	C14—C15—C16	121.2 (8)
C19—C18—S1	110.37 (13)	C14—C15—H15	119.4
C17—C18—S1	104.75 (12)	C16—C15—H15	119.4
C19—C18—H18	108.4	C11—C16—C15	118.8 (8)
C17—C18—H18	108.4	C11—C16—H16	120.6
S1—C18—H18	108.4	C15—C16—H16	120.6
C20—C19—C24	116.24 (19)	C11—C12'—C13'	114.9 (9)
C20—C19—C18	121.07 (18)	C11—C12'—H12'	122.5
C24—C19—C18	122.69 (18)	C13'—C12'—H12'	122.5
C21—C20—C19	123.2 (2)	C14—C13'—C12'	124.9 (9)
C21—C20—Cl1	117.18 (16)	C14—C13'—H13'	117.5
C19—C20—Cl1	119.57 (16)	C12'—C13'—H13'	117.5
C22—C21—C20	118.2 (2)	C14—C15'—C16'	118.3 (11)
C22—C21—H21	120.9	C14—C15'—H15'	120.9
C20—C21—H21	120.9	C16'—C15'—H15'	120.9
C23—C22—C21	120.9 (2)	C11—C16'—C15'	122.7 (11)
C23—C22—Cl2	120.38 (18)	C11—C16'—H16'	118.7
C21—C22—Cl2	118.75 (19)	C15'—C16'—H16'	118.7
C22—C23—C24	119.8 (2)
N1—C2—C3—C10	−179.85 (18)	C7—C2—N1—C6	−178.41 (19)
C7—C2—C3—C10	−0.5 (3)	C3—C2—N1—C6	1.0 (3)
N1—C2—C3—C4	−0.7 (3)	C4—C5—S1—C18	168.69 (17)
C7—C2—C3—C4	178.65 (19)	C6—C5—S1—C18	−13.48 (15)
C2—C3—C4—C5	−0.9 (3)	C19—C18—S1—C5	−99.75 (15)
C10—C3—C4—C5	178.20 (17)	C17—C18—S1—C5	26.24 (15)
C2—C3—C4—C11	178.78 (17)	C5—C4—C11—C12	82.4 (4)
C10—C3—C4—C11	−2.1 (3)	C3—C4—C11—C12	−97.3 (4)
C3—C4—C5—C6	2.2 (3)	C5—C4—C11—C16'	−68.1 (5)
C11—C4—C5—C6	−177.50 (17)	C3—C4—C11—C16'	112.3 (5)
C3—C4—C5—S1	179.84 (14)	C5—C4—C11—C16	−97.3 (5)
C11—C4—C5—S1	0.2 (3)	C3—C4—C11—C16	83.0 (5)
C4—C5—C6—N1	−2.1 (3)	C5—C4—C11—C12'	107.1 (4)
S1—C5—C6—N1	179.96 (16)	C3—C4—C11—C12'	−72.5 (4)
C4—C5—C6—C17	173.78 (17)	C16'—C11—C12—C13	−25.1 (9)
S1—C5—C6—C17	−4.2 (2)	C16—C11—C12—C13	1.1 (9)
N1—C2—C7—C8	179.8 (2)	C12'—C11—C12—C13	99 (2)
C3—C2—C7—C8	0.4 (3)	C4—C11—C12—C13	−178.6 (6)
C2—C7—C8—C9	−0.2 (4)	C15'—C14—C13—C12	24.1 (10)
C7—C8—C9—C10	0.1 (4)	C13'—C14—C13—C12	−74 (2)
C8—C9—C10—C3	−0.2 (3)	C15—C14—C13—C12	−5.3 (10)
C2—C3—C10—C9	0.4 (3)	C11—C12—C13—C14	2.3 (11)
C4—C3—C10—C9	−178.69 (19)	C13—C14—C15—C16	5.1 (12)
N1—C6—C17—C18	−159.49 (18)	C15'—C14—C15—C16	−85 (2)
C5—C6—C17—C18	24.6 (2)	C13'—C14—C15—C16	25.4 (11)
C6—C17—C18—C19	90.0 (2)	C12—C11—C16—C15	−1.5 (10)
C6—C17—C18—S1	−32.2 (2)	C16'—C11—C16—C15	77 (2)
C17—C18—C19—C20	170.37 (17)	C12'—C11—C16—C15	−26.2 (10)
S1—C18—C19—C20	−70.5 (2)	C4—C11—C16—C15	178.2 (6)
C17—C18—C19—C24	−9.6 (3)	C14—C15—C16—C11	−1.4 (12)
S1—C18—C19—C24	109.51 (18)	C12—C11—C12'—C13'	−67 (2)
C24—C19—C20—C21	−0.2 (3)	C16'—C11—C12'—C13'	−1.9 (9)
C18—C19—C20—C21	179.80 (17)	C16—C11—C12'—C13'	26.7 (8)
C24—C19—C20—Cl1	−179.75 (14)	C4—C11—C12'—C13'	−177.2 (5)
C18—C19—C20—Cl1	0.2 (2)	C13—C14—C13'—C12'	96 (3)
C19—C20—C21—C22	0.8 (3)	C15'—C14—C13'—C12'	2.8 (12)
Cl1—C20—C21—C22	−179.67 (15)	C15—C14—C13'—C12'	−24.8 (10)
C20—C21—C22—C23	−0.4 (3)	C11—C12'—C13'—C14	−0.6 (11)
C20—C21—C22—Cl2	−179.36 (15)	C13—C14—C15'—C16'	−25.4 (12)
C21—C22—C23—C24	−0.6 (3)	C13'—C14—C15'—C16'	−2.3 (12)
Cl2—C22—C23—C24	178.41 (15)	C15—C14—C15'—C16'	78.8 (19)
C22—C23—C24—C19	1.2 (3)	C12—C11—C16'—C15'	23.5 (10)
C20—C19—C24—C23	−0.8 (3)	C16—C11—C16'—C15'	−88 (2)
C18—C19—C24—C23	179.23 (18)	C12'—C11—C16'—C15'	2.3 (11)
C5—C6—N1—C2	0.4 (3)	C4—C11—C16'—C15'	177.4 (7)
C17—C6—N1—C2	−175.03 (18)	C14—C15'—C16'—C11	−0.1 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg2i	0.93	2.92	3.818 (2)	162
C21—H21···Cg3ii	0.93	2.71	3.636 (2)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cg2i	0.93	2.92	3.818 (2)	162
C21—H21⋯Cg3ii	0.93	2.71	3.636 (2)	172

Symmetry codes: (i) ; (ii) . Cg2 and Cg3 are the centroids of the N1/C2–C6 and C2/C3/C7–C10 rings, respectively.