Ethyl 2-(2,6-difluoro-benz-yloxy)-4-(4,6-dimethoxy-pyrimidin-2-yl)quinoline-3-carboxyl-ate.

In the title compound, C(25)H(21)F(2)N(3)O(5), the pyrimidine and difluoro-benz-yloxy rings are twisted away from the central quinoline ring system, making dihedral angles of 54.6 (1) and 74.1 (1)°, respectively. A weak C-H⋯O inter-action links symmetry-related mol-ecules, forming a pseudo-dimer. π-π inter-actions between the quinoline rings of symmetry-related mol-ecules [centroid-centroid distance = 3.5479 (10) Å] link these dimers into chains parallel to [101]. Weak C-H⋯π inter-actions join adjacent chains, forming a two-dimensional layer parallel to (101).

Related literature

Pyrimidinylbenzoates are highly effective herbicides with acetohydr­oxy acid synthase (AHAS) as target, see: Duggleby & Pang (2000 ▶). For related structures, see: Li & Huang (2007 ▶); Li & Wang (2007 ▶); Li et al. (2006 ▶).

Experimental

Crystal data

C25H21F2N3O5

M = 481.45

Triclinic,

a = 9.6623 (6) Å

b = 10.7044 (6) Å

c = 11.3856 (7) Å

α = 84.466 (1)°

β = 82.251 (2)°

γ = 81.394 (1)°

V = 1150.21 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 297 K

0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.959, T max = 0.989

12431 measured reflections

4954 independent reflections

3541 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.170

S = 1.06

4954 reflections

319 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030499/dn2477sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030499/dn2477Isup2.hkl

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

C25H21F2N3O5	Z = 2
Mr = 481.45	F(000) = 500
Triclinic, P1	Dx = 1.390 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6623 (6) Å	Cell parameters from 4454 reflections
b = 10.7044 (6) Å	θ = 2.5–27.9°
c = 11.3856 (7) Å	µ = 0.11 mm−1
α = 84.466 (1)°	T = 297 K
β = 82.251 (2)°	Block, colourless
γ = 81.394 (1)°	0.20 × 0.20 × 0.10 mm
V = 1150.21 (12) Å3

Bruker SMART APEX CCD area-detector diffractometer	4954 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	3541 reflections with I > 2σ(I)
graphite	Rint = 0.035
0.3° wide ω exposures scans	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −12→12
Tmin = 0.959, Tmax = 0.989	k = −13→13
12431 measured reflections	l = −14→14

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1077P)2 + 0.004P] where P = (Fo2 + 2Fc2)/3
4954 reflections	(Δ/σ)max < 0.001
319 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.23 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
C1	−0.11250 (16)	1.02922 (15)	0.13717 (14)	0.0399 (4)
C2	−0.20285 (19)	1.12507 (18)	0.08156 (17)	0.0518 (4)
H2	−0.1963	1.2096	0.0892	0.062*
C3	−0.3002 (2)	1.09504 (19)	0.01640 (17)	0.0559 (5)
H3	−0.3596	1.1593	−0.0200	0.067*
C4	−0.31136 (19)	0.96834 (19)	0.00409 (17)	0.0535 (5)
H4	−0.3772	0.9490	−0.0414	0.064*
C5	−0.22682 (18)	0.87332 (17)	0.05793 (15)	0.0467 (4)
H5	−0.2358	0.7894	0.0496	0.056*
C6	−0.12486 (16)	0.90099 (15)	0.12685 (13)	0.0382 (4)
C7	−0.02903 (16)	0.80657 (15)	0.18258 (14)	0.0379 (4)
C8	0.07269 (16)	0.84312 (14)	0.23904 (14)	0.0378 (4)
C9	0.07460 (16)	0.97547 (15)	0.24412 (14)	0.0397 (4)
C10	−0.03328 (16)	0.66870 (15)	0.17606 (13)	0.0378 (4)
C11	−0.15329 (17)	0.50141 (15)	0.20841 (15)	0.0439 (4)
C12	−0.03457 (18)	0.42061 (16)	0.17093 (16)	0.0474 (4)
H12	−0.0349	0.3339	0.1700	0.057*
C13	0.08520 (18)	0.47704 (15)	0.13469 (15)	0.0428 (4)
C14	−0.3984 (2)	0.5352 (2)	0.2799 (2)	0.0682 (6)
H14A	−0.3829	0.5797	0.3452	0.102*
H14B	−0.4753	0.4874	0.3041	0.102*
H14C	−0.4207	0.5951	0.2145	0.102*
C15	0.3280 (2)	0.4621 (2)	0.0603 (2)	0.0650 (5)
H15A	0.3116	0.5246	−0.0044	0.097*
H15B	0.4055	0.3993	0.0354	0.097*
H15C	0.3501	0.5021	0.1261	0.097*
C16	0.17828 (19)	0.75111 (15)	0.29953 (15)	0.0439 (4)
C17	0.1993 (3)	0.5997 (2)	0.4653 (2)	0.0774 (7)
H17A	0.1614	0.6036	0.5484	0.093*
H17B	0.2941	0.6220	0.4559	0.093*
C18	0.2047 (3)	0.4705 (2)	0.4309 (2)	0.0838 (7)
H18A	0.1105	0.4507	0.4343	0.126*
H18B	0.2555	0.4119	0.4845	0.126*
H18C	0.2516	0.4643	0.3514	0.126*
C19	0.17799 (19)	1.13573 (16)	0.31615 (18)	0.0514 (5)
H19A	0.0887	1.1728	0.3567	0.062*
H19B	0.1933	1.1807	0.2384	0.062*
C20	0.29534 (18)	1.14504 (15)	0.38676 (16)	0.0445 (4)
C21	0.2822 (2)	1.12069 (18)	0.50781 (18)	0.0598 (5)
C22	0.3845 (3)	1.1322 (2)	0.5770 (2)	0.0815 (8)
H22	0.3701	1.1150	0.6590	0.098*
C23	0.5084 (3)	1.1696 (2)	0.5223 (3)	0.0841 (8)
H23	0.5792	1.1781	0.5676	0.101*
C24	0.5287 (2)	1.1944 (2)	0.4020 (3)	0.0767 (7)
H24	0.6129	1.2195	0.3648	0.092*
C25	0.4223 (2)	1.18172 (18)	0.33639 (19)	0.0555 (5)
F1	0.16058 (16)	1.08091 (16)	0.55995 (13)	0.0978 (5)
F2	0.44154 (15)	1.20738 (14)	0.21759 (13)	0.0900 (5)
N1	−0.01274 (14)	1.06487 (12)	0.19857 (12)	0.0431 (3)
N2	0.08787 (14)	0.60077 (13)	0.13662 (12)	0.0415 (3)
N3	−0.15616 (14)	0.62592 (13)	0.21236 (12)	0.0435 (3)
O1	−0.27320 (13)	0.45076 (12)	0.24386 (13)	0.0572 (4)
O2	0.20379 (13)	0.40262 (12)	0.09621 (12)	0.0580 (4)
O3	0.30275 (14)	0.73618 (13)	0.27045 (13)	0.0606 (4)
O4	0.11257 (15)	0.68999 (12)	0.39364 (12)	0.0596 (4)
O5	0.17624 (12)	1.00344 (10)	0.30413 (11)	0.0485 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0371 (8)	0.0391 (9)	0.0455 (9)	−0.0126 (7)	−0.0069 (7)	0.0001 (7)
C2	0.0490 (10)	0.0417 (9)	0.0676 (12)	−0.0110 (8)	−0.0175 (9)	0.0032 (8)
C3	0.0509 (11)	0.0558 (11)	0.0623 (11)	−0.0051 (9)	−0.0198 (9)	0.0044 (9)
C4	0.0453 (10)	0.0634 (12)	0.0571 (11)	−0.0112 (9)	−0.0203 (8)	−0.0056 (9)
C5	0.0449 (9)	0.0472 (10)	0.0533 (10)	−0.0138 (7)	−0.0150 (7)	−0.0063 (7)
C6	0.0352 (8)	0.0413 (9)	0.0410 (8)	−0.0122 (7)	−0.0073 (6)	−0.0027 (6)
C7	0.0390 (8)	0.0360 (8)	0.0419 (8)	−0.0137 (6)	−0.0069 (6)	−0.0029 (6)
C8	0.0378 (8)	0.0329 (8)	0.0464 (9)	−0.0124 (6)	−0.0108 (7)	−0.0022 (6)
C9	0.0385 (8)	0.0357 (8)	0.0495 (9)	−0.0154 (7)	−0.0119 (7)	−0.0020 (7)
C10	0.0402 (8)	0.0360 (8)	0.0422 (8)	−0.0126 (6)	−0.0144 (6)	−0.0041 (6)
C11	0.0468 (10)	0.0412 (9)	0.0512 (9)	−0.0201 (7)	−0.0213 (7)	0.0019 (7)
C12	0.0550 (10)	0.0336 (8)	0.0616 (11)	−0.0168 (8)	−0.0227 (8)	−0.0049 (7)
C13	0.0476 (9)	0.0376 (9)	0.0492 (9)	−0.0106 (7)	−0.0182 (7)	−0.0085 (7)
C14	0.0474 (11)	0.0685 (14)	0.0941 (16)	−0.0252 (10)	−0.0097 (10)	−0.0055 (11)
C15	0.0515 (11)	0.0654 (13)	0.0776 (14)	−0.0086 (10)	−0.0020 (10)	−0.0108 (11)
C16	0.0513 (10)	0.0331 (8)	0.0542 (10)	−0.0139 (7)	−0.0213 (8)	−0.0048 (7)
C17	0.1054 (18)	0.0602 (13)	0.0727 (14)	−0.0146 (12)	−0.0449 (13)	0.0172 (11)
C18	0.1047 (19)	0.0519 (13)	0.1008 (18)	−0.0081 (12)	−0.0420 (15)	0.0019 (12)
C19	0.0514 (10)	0.0326 (9)	0.0774 (12)	−0.0126 (7)	−0.0247 (9)	−0.0068 (8)
C20	0.0461 (9)	0.0311 (8)	0.0616 (11)	−0.0103 (7)	−0.0155 (8)	−0.0101 (7)
C21	0.0686 (13)	0.0479 (11)	0.0653 (12)	−0.0085 (9)	−0.0097 (10)	−0.0141 (9)
C22	0.120 (2)	0.0638 (14)	0.0692 (14)	−0.0051 (14)	−0.0414 (14)	−0.0200 (11)
C23	0.1000 (19)	0.0523 (13)	0.119 (2)	−0.0128 (13)	−0.0703 (17)	−0.0179 (13)
C24	0.0579 (13)	0.0531 (12)	0.131 (2)	−0.0246 (10)	−0.0378 (13)	−0.0045 (13)
C25	0.0548 (11)	0.0440 (10)	0.0733 (13)	−0.0174 (8)	−0.0191 (9)	−0.0007 (9)
F1	0.0910 (10)	0.1135 (12)	0.0842 (10)	−0.0252 (9)	0.0183 (8)	−0.0065 (8)
F2	0.0820 (9)	0.1069 (12)	0.0810 (9)	−0.0321 (8)	−0.0064 (7)	0.0174 (8)
N1	0.0414 (7)	0.0344 (7)	0.0575 (9)	−0.0139 (6)	−0.0137 (6)	0.0002 (6)
N2	0.0443 (8)	0.0374 (7)	0.0475 (8)	−0.0127 (6)	−0.0122 (6)	−0.0066 (6)
N3	0.0433 (8)	0.0389 (8)	0.0539 (8)	−0.0171 (6)	−0.0131 (6)	−0.0040 (6)
O1	0.0496 (7)	0.0471 (7)	0.0822 (9)	−0.0258 (6)	−0.0164 (6)	−0.0001 (6)
O2	0.0518 (8)	0.0441 (7)	0.0809 (9)	−0.0077 (6)	−0.0085 (6)	−0.0169 (6)
O3	0.0431 (7)	0.0551 (8)	0.0882 (10)	−0.0084 (6)	−0.0251 (6)	−0.0016 (7)
O4	0.0696 (9)	0.0501 (8)	0.0614 (8)	−0.0137 (6)	−0.0221 (7)	0.0121 (6)
O5	0.0503 (7)	0.0322 (6)	0.0715 (8)	−0.0135 (5)	−0.0286 (6)	−0.0050 (5)

C1—N1	1.381 (2)	C14—H14C	0.9600
C1—C2	1.404 (2)	C15—O2	1.435 (2)
C1—C6	1.413 (2)	C15—H15A	0.9600
C2—C3	1.365 (2)	C15—H15B	0.9600
C2—H2	0.9300	C15—H15C	0.9600
C3—C4	1.398 (3)	C16—O3	1.194 (2)
C3—H3	0.9300	C16—O4	1.336 (2)
C4—C5	1.358 (3)	C17—O4	1.446 (2)
C4—H4	0.9300	C17—C18	1.465 (3)
C5—C6	1.419 (2)	C17—H17A	0.9700
C5—H5	0.9300	C17—H17B	0.9700
C6—C7	1.427 (2)	C18—H18A	0.9600
C7—C8	1.366 (2)	C18—H18B	0.9600
C7—C10	1.492 (2)	C18—H18C	0.9600
C8—C9	1.426 (2)	C19—O5	1.4386 (18)
C8—C16	1.498 (2)	C19—C20	1.496 (2)
C9—N1	1.295 (2)	C19—H19A	0.9700
C9—O5	1.3525 (18)	C19—H19B	0.9700
C10—N2	1.329 (2)	C20—C21	1.370 (3)
C10—N3	1.336 (2)	C20—C25	1.378 (3)
C11—N3	1.334 (2)	C21—F1	1.352 (2)
C11—O1	1.3487 (19)	C21—C22	1.370 (3)
C11—C12	1.374 (2)	C22—C23	1.370 (4)
C12—C13	1.381 (2)	C22—H22	0.9300
C12—H12	0.9300	C23—C24	1.363 (4)
C13—N2	1.331 (2)	C23—H23	0.9300
C13—O2	1.341 (2)	C24—C25	1.380 (3)
C14—O1	1.435 (2)	C24—H24	0.9300
C14—H14A	0.9600	C25—F2	1.347 (2)
C14—H14B	0.9600
N1—C1—C2	118.10 (14)	H15A—C15—H15C	109.5
N1—C1—C6	122.54 (14)	H15B—C15—H15C	109.5
C2—C1—C6	119.36 (14)	O3—C16—O4	124.76 (16)
C3—C2—C1	120.49 (17)	O3—C16—C8	125.61 (16)
C3—C2—H2	119.8	O4—C16—C8	109.61 (15)
C1—C2—H2	119.8	O4—C17—C18	111.28 (18)
C2—C3—C4	120.44 (17)	O4—C17—H17A	109.4
C2—C3—H3	119.8	C18—C17—H17A	109.4
C4—C3—H3	119.8	O4—C17—H17B	109.4
C5—C4—C3	120.58 (16)	C18—C17—H17B	109.4
C5—C4—H4	119.7	H17A—C17—H17B	108.0
C3—C4—H4	119.7	C17—C18—H18A	109.5
C4—C5—C6	120.53 (16)	C17—C18—H18B	109.5
C4—C5—H5	119.7	H18A—C18—H18B	109.5
C6—C5—H5	119.7	C17—C18—H18C	109.5
C1—C6—C5	118.59 (14)	H18A—C18—H18C	109.5
C1—C6—C7	117.55 (13)	H18B—C18—H18C	109.5
C5—C6—C7	123.81 (14)	O5—C19—C20	107.44 (13)
C8—C7—C6	119.30 (14)	O5—C19—H19A	110.2
C8—C7—C10	119.15 (14)	C20—C19—H19A	110.2
C6—C7—C10	121.50 (13)	O5—C19—H19B	110.2
C7—C8—C9	118.12 (14)	C20—C19—H19B	110.2
C7—C8—C16	123.18 (14)	H19A—C19—H19B	108.5
C9—C8—C16	118.67 (13)	C21—C20—C25	115.06 (17)
N1—C9—O5	120.62 (13)	C21—C20—C19	121.87 (17)
N1—C9—C8	125.03 (14)	C25—C20—C19	123.05 (17)
O5—C9—C8	114.34 (13)	F1—C21—C20	116.70 (18)
N2—C10—N3	126.87 (14)	F1—C21—C22	119.1 (2)
N2—C10—C7	115.84 (14)	C20—C21—C22	124.1 (2)
N3—C10—C7	117.27 (14)	C23—C22—C21	118.3 (2)
N3—C11—O1	118.56 (15)	C23—C22—H22	120.8
N3—C11—C12	123.87 (15)	C21—C22—H22	120.8
O1—C11—C12	117.57 (15)	C24—C23—C22	120.5 (2)
C11—C12—C13	115.41 (15)	C24—C23—H23	119.8
C11—C12—H12	122.3	C22—C23—H23	119.8
C13—C12—H12	122.3	C23—C24—C25	118.9 (2)
N2—C13—O2	119.06 (15)	C23—C24—H24	120.5
N2—C13—C12	123.08 (16)	C25—C24—H24	120.5
O2—C13—C12	117.86 (15)	F2—C25—C20	117.91 (16)
O1—C14—H14A	109.5	F2—C25—C24	119.04 (19)
O1—C14—H14B	109.5	C20—C25—C24	123.0 (2)
H14A—C14—H14B	109.5	C9—N1—C1	117.38 (13)
O1—C14—H14C	109.5	C10—N2—C13	115.82 (14)
H14A—C14—H14C	109.5	C11—N3—C10	114.94 (14)
H14B—C14—H14C	109.5	C11—O1—C14	117.78 (14)
O2—C15—H15A	109.5	C13—O2—C15	117.34 (14)
O2—C15—H15B	109.5	C16—O4—C17	117.21 (17)
H15A—C15—H15B	109.5	C9—O5—C19	116.23 (12)
O2—C15—H15C	109.5
N1—C1—C2—C3	177.81 (17)	C25—C20—C21—F1	−178.15 (16)
C6—C1—C2—C3	−1.1 (3)	C19—C20—C21—F1	3.6 (3)
C1—C2—C3—C4	0.0 (3)	C25—C20—C21—C22	0.7 (3)
C2—C3—C4—C5	0.8 (3)	C19—C20—C21—C22	−177.59 (18)
C3—C4—C5—C6	−0.5 (3)	F1—C21—C22—C23	178.40 (19)
N1—C1—C6—C5	−177.47 (15)	C20—C21—C22—C23	−0.4 (3)
C2—C1—C6—C5	1.4 (2)	C21—C22—C23—C24	−0.1 (3)
N1—C1—C6—C7	−0.2 (2)	C22—C23—C24—C25	0.2 (4)
C2—C1—C6—C7	178.70 (15)	C21—C20—C25—F2	−179.82 (17)
C4—C5—C6—C1	−0.6 (3)	C19—C20—C25—F2	−1.5 (3)
C4—C5—C6—C7	−177.72 (16)	C21—C20—C25—C24	−0.5 (3)
C1—C6—C7—C8	−2.4 (2)	C19—C20—C25—C24	177.74 (17)
C5—C6—C7—C8	174.76 (15)	C23—C24—C25—F2	179.4 (2)
C1—C6—C7—C10	−179.66 (14)	C23—C24—C25—C20	0.1 (3)
C5—C6—C7—C10	−2.5 (2)	O5—C9—N1—C1	179.15 (14)
C6—C7—C8—C9	2.7 (2)	C8—C9—N1—C1	−2.2 (2)
C10—C7—C8—C9	180.00 (14)	C2—C1—N1—C9	−176.48 (15)
C6—C7—C8—C16	−179.72 (15)	C6—C1—N1—C9	2.4 (2)
C10—C7—C8—C16	−2.4 (2)	N3—C10—N2—C13	−0.7 (2)
C7—C8—C9—N1	−0.4 (2)	C7—C10—N2—C13	177.77 (13)
C16—C8—C9—N1	−178.08 (16)	O2—C13—N2—C10	−179.84 (14)
C7—C8—C9—O5	178.39 (14)	C12—C13—N2—C10	0.0 (2)
C16—C8—C9—O5	0.7 (2)	O1—C11—N3—C10	179.87 (14)
C8—C7—C10—N2	−50.7 (2)	C12—C11—N3—C10	0.3 (2)
C6—C7—C10—N2	126.58 (16)	N2—C10—N3—C11	0.5 (2)
C8—C7—C10—N3	127.95 (16)	C7—C10—N3—C11	−177.91 (13)
C6—C7—C10—N3	−54.8 (2)	N3—C11—O1—C14	2.2 (2)
N3—C11—C12—C13	−0.9 (2)	C12—C11—O1—C14	−178.28 (16)
O1—C11—C12—C13	179.53 (14)	N2—C13—O2—C15	0.7 (2)
C11—C12—C13—N2	0.8 (2)	C12—C13—O2—C15	−179.17 (16)
C11—C12—C13—O2	−179.41 (15)	O3—C16—O4—C17	0.2 (3)
C7—C8—C16—O3	115.1 (2)	C8—C16—O4—C17	−178.10 (15)
C9—C8—C16—O3	−67.3 (2)	C18—C17—O4—C16	−96.3 (2)
C7—C8—C16—O4	−66.5 (2)	N1—C9—O5—C19	1.6 (2)
C9—C8—C16—O4	111.05 (16)	C8—C9—O5—C19	−177.26 (14)
O5—C19—C20—C21	−77.8 (2)	C20—C19—O5—C9	178.85 (14)
O5—C19—C20—C25	104.00 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N3	0.93	2.54	3.075 (2)	117
C23—H23···O3i	0.93	2.60	3.476 (2)	158
C18—H18B···Cg3ii	0.96	2.91	3.612 (2)	131

Cg(I)–Cg(J)	Cg–Cg	α	(CgI–CgJ)Perp	(CgJ–CgI)Perp	Slippage
Cg1–Cg2iii	3.5479 (10)	3.27	3.482	3.483	0.676

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯O3i	0.93	2.60	3.476 (2)	158
C18—H18B⋯Cg3ii	0.96	2.91	3.612 (2)	131

Symmetry codes: (i) ; (ii) .

Table 2

Table 2. π-π stacking in the title compound (Å, °)

CgI–CgJ	Cg–Cg	α	(Cg–Cg)Perp	(CgJ–CgI)Perp	Slippage
Cg1–Cg2iii	3.5479 (10)	3.27	3.482	3.483	0.676

Cg1 and Cg2 are the centroids of the N1,C1,C6–C9 and C1–C6 rings, respectively, and α is the angle between the corresponding planes. Symmetry code: (iii)