Ethyl 6-chloro-2-[(2-chloro-7,8-dimethyl-quinolin-3-yl)meth-oxy]-4-phenyl-quinoline-3-carboxyl-ate.

In the title compound, C(30)H(24)Cl(2)N(2)O(3), the two quinoline ring systems are almost planar [maximum deviations = 0.029 (2) and 0.018 (3) Å] and the dihedral angle between them is 4.17 (8)°. The dihedral angle between the phenyl ring and its attached quinoline ring is 69.06 (13)°. The packing is stabilized by C-H⋯O, C-H⋯N, weak π-π stacking [centroid-centroid distances = 3.7985 (16) and 3.7662 (17) Å] and C-H⋯π inter-actions.

Related literature

For related structures, see: Khan et al. (2009 ▶, 2010a ▶,b ▶); Roopan et al. (2009 ▶). For background to quinolines, see: Roopan & Khan (2009 ▶); Savini et al. (2001 ▶).

Experimental

Crystal data

C30H24Cl2N2O3

M = 531.41

Monoclinic,

a = 8.3187 (5) Å

b = 28.0038 (17) Å

c = 11.2093 (7) Å

β = 98.721 (6)°

V = 2581.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 295 K

0.29 × 0.24 × 0.20 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T min = 0.921, T max = 0.944

25780 measured reflections

4808 independent reflections

1857 reflections with I > 2σ(I)

R int = 0.123

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.072

S = 0.81

4808 reflections

337 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011335/hb5374sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011335/hb5374Isup2.hkl

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

C30H24Cl2N2O3	F(000) = 1104
Mr = 531.41	Dx = 1.367 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 985 reflections
a = 8.3187 (5) Å	θ = 2.6–25.5°
b = 28.0038 (17) Å	µ = 0.29 mm−1
c = 11.2093 (7) Å	T = 295 K
β = 98.721 (6)°	Block, colourless
V = 2581.1 (3) Å3	0.29 × 0.24 × 0.20 mm
Z = 4

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	4808 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1857 reflections with I > 2σ(I)
graphite	Rint = 0.123
ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	h = −10→10
Tmin = 0.921, Tmax = 0.944	k = −33→33
25780 measured reflections	l = −13→13

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H-atom parameters constrained
S = 0.81	w = 1/[σ2(Fo2) + (0.0132P)2] where P = (Fo2 + 2Fc2)/3
4808 reflections	(Δ/σ)max < 0.001
337 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl1	0.41574 (10)	−0.09830 (3)	0.17492 (7)	0.0664 (3)
Cl2	−0.16048 (10)	0.18075 (3)	0.62865 (7)	0.0769 (4)
O1	0.1593 (2)	0.03957 (7)	0.09664 (16)	0.0491 (8)
O2	−0.0023 (3)	0.10440 (8)	−0.08652 (19)	0.0761 (10)
O3	0.1613 (2)	0.16113 (8)	0.00331 (17)	0.0582 (9)
N1	0.4330 (3)	−0.09180 (8)	−0.0534 (2)	0.0431 (10)
N2	0.0969 (3)	0.05269 (8)	0.2868 (2)	0.0408 (10)
C1	0.3783 (3)	−0.07019 (10)	0.0336 (3)	0.0414 (11)
C2	0.2954 (3)	−0.02581 (10)	0.0283 (3)	0.0379 (12)
C3	0.2746 (3)	−0.00415 (10)	−0.0811 (3)	0.0417 (11)
C4	0.3142 (3)	−0.00413 (11)	−0.2960 (3)	0.0504 (12)
C5	0.3682 (4)	−0.02691 (12)	−0.3888 (3)	0.0546 (14)
C6	0.4432 (3)	−0.07216 (12)	−0.3737 (3)	0.0480 (12)
C7	0.4630 (3)	−0.09424 (11)	−0.2636 (3)	0.0432 (11)
C8	0.4087 (3)	−0.07039 (11)	−0.1658 (3)	0.0395 (12)
C9	0.3322 (3)	−0.02535 (10)	−0.1802 (3)	0.0378 (12)
C10	0.5389 (3)	−0.14318 (10)	−0.2462 (3)	0.0614 (14)
C11	0.4988 (3)	−0.09507 (11)	−0.4838 (2)	0.0705 (14)
C12	0.2312 (3)	−0.00526 (9)	0.1354 (3)	0.0453 (12)
C13	0.0961 (3)	0.06702 (11)	0.1771 (3)	0.0410 (12)
C14	0.0399 (3)	0.11247 (10)	0.1293 (3)	0.0372 (12)
C15	−0.0212 (3)	0.14355 (10)	0.2034 (3)	0.0358 (11)
C16	−0.0267 (3)	0.12959 (11)	0.3255 (3)	0.0357 (11)
C17	−0.0888 (3)	0.15872 (10)	0.4103 (3)	0.0436 (12)
C18	−0.0858 (3)	0.14366 (12)	0.5255 (3)	0.0491 (12)
C19	−0.0249 (3)	0.09918 (12)	0.5634 (3)	0.0548 (14)
C20	0.0334 (3)	0.06967 (11)	0.4830 (3)	0.0483 (12)
C21	0.0335 (3)	0.08365 (11)	0.3622 (3)	0.0403 (12)
C22	0.0606 (4)	0.12451 (12)	0.0010 (3)	0.0479 (14)
C23	0.1936 (4)	0.18050 (13)	−0.1109 (3)	0.0786 (17)
C24	0.1264 (5)	0.22927 (12)	−0.1233 (3)	0.117 (2)
C25	−0.0804 (4)	0.19251 (10)	0.1607 (3)	0.0383 (12)
C26	−0.2210 (4)	0.19679 (11)	0.0785 (3)	0.0546 (12)
C27	−0.2764 (4)	0.24215 (13)	0.0418 (3)	0.0706 (17)
C28	−0.1930 (5)	0.28234 (12)	0.0844 (3)	0.0725 (17)
C29	−0.0541 (4)	0.27775 (12)	0.1640 (3)	0.0652 (16)
C30	0.0047 (3)	0.23285 (12)	0.2034 (3)	0.0548 (14)
H3	0.22160	0.02510	−0.09080	0.0500*
H4	0.26490	0.02560	−0.30850	0.0610*
H5	0.35560	−0.01240	−0.46430	0.0660*
H10A	0.46760	−0.16630	−0.28950	0.0920*
H10B	0.55640	−0.15100	−0.16180	0.0920*
H10C	0.64110	−0.14330	−0.27610	0.0920*
H11A	0.61550	−0.09610	−0.47270	0.1060*
H11B	0.45970	−0.07660	−0.55440	0.1060*
H11C	0.45630	−0.12690	−0.49370	0.1060*
H12A	0.15080	−0.02640	0.16140	0.0550*
H12B	0.31880	−0.00070	0.20220	0.0550*
H17	−0.13210	0.18850	0.38710	0.0530*
H19	−0.02390	0.08950	0.64290	0.0660*
H20	0.07380	0.03980	0.50840	0.0580*
H23A	0.14290	0.16070	−0.17710	0.0940*
H23B	0.30980	0.18120	−0.11270	0.0940*
H24A	0.01300	0.22850	−0.11590	0.1760*
H24B	0.13930	0.24190	−0.20100	0.1760*
H24C	0.18330	0.24920	−0.06120	0.1760*
H26	−0.27790	0.16970	0.04800	0.0650*
H27	−0.37200	0.24520	−0.01270	0.0850*
H28	−0.23130	0.31240	0.05910	0.0870*
H29	0.00310	0.30500	0.19280	0.0780*
H30	0.10030	0.23020	0.25800	0.0660*

	U11	U22	U33	U12	U13	U23
Cl1	0.0992 (7)	0.0524 (5)	0.0464 (6)	0.0156 (5)	0.0069 (5)	0.0096 (5)
Cl2	0.0844 (6)	0.0995 (8)	0.0504 (6)	0.0134 (6)	0.0214 (5)	−0.0159 (6)
O1	0.0695 (15)	0.0410 (13)	0.0387 (14)	0.0177 (12)	0.0145 (11)	0.0021 (12)
O2	0.111 (2)	0.0710 (17)	0.0426 (17)	−0.0241 (16)	0.0002 (14)	−0.0091 (14)
O3	0.0746 (16)	0.0637 (16)	0.0393 (15)	−0.0123 (14)	0.0185 (12)	0.0066 (13)
N1	0.0479 (17)	0.0351 (16)	0.0463 (18)	0.0037 (13)	0.0073 (14)	−0.0069 (15)
N2	0.0441 (16)	0.0414 (17)	0.0374 (17)	0.0010 (13)	0.0080 (14)	0.0012 (15)
C1	0.052 (2)	0.0300 (19)	0.040 (2)	0.0020 (17)	0.0001 (17)	0.0026 (17)
C2	0.040 (2)	0.035 (2)	0.037 (2)	−0.0036 (16)	0.0005 (16)	−0.0030 (17)
C3	0.042 (2)	0.0336 (19)	0.049 (2)	0.0054 (16)	0.0058 (17)	−0.0024 (18)
C4	0.058 (2)	0.050 (2)	0.044 (2)	0.0052 (18)	0.0101 (18)	0.002 (2)
C5	0.062 (2)	0.062 (3)	0.040 (2)	−0.003 (2)	0.0089 (18)	0.006 (2)
C6	0.041 (2)	0.058 (2)	0.046 (2)	−0.0081 (19)	0.0101 (18)	−0.013 (2)
C7	0.0334 (19)	0.045 (2)	0.050 (2)	−0.0063 (17)	0.0027 (17)	−0.012 (2)
C8	0.039 (2)	0.041 (2)	0.038 (2)	−0.0057 (17)	0.0039 (16)	−0.0024 (18)
C9	0.042 (2)	0.034 (2)	0.037 (2)	−0.0003 (17)	0.0049 (16)	−0.0016 (18)
C10	0.058 (2)	0.060 (2)	0.068 (3)	0.004 (2)	0.0154 (18)	−0.013 (2)
C11	0.075 (2)	0.085 (3)	0.055 (2)	−0.010 (2)	0.0216 (19)	−0.015 (2)
C12	0.057 (2)	0.035 (2)	0.043 (2)	0.0024 (17)	0.0045 (17)	0.0048 (17)
C13	0.038 (2)	0.044 (2)	0.041 (2)	0.0028 (18)	0.0056 (17)	−0.008 (2)
C14	0.043 (2)	0.037 (2)	0.031 (2)	−0.0002 (17)	0.0039 (16)	0.0036 (17)
C15	0.0320 (19)	0.036 (2)	0.039 (2)	−0.0060 (16)	0.0044 (16)	0.0016 (17)
C16	0.0286 (18)	0.039 (2)	0.040 (2)	−0.0006 (16)	0.0073 (16)	−0.0008 (17)
C17	0.039 (2)	0.048 (2)	0.044 (2)	0.0028 (17)	0.0067 (17)	0.0008 (19)
C18	0.043 (2)	0.061 (2)	0.044 (2)	0.0015 (19)	0.0092 (17)	−0.004 (2)
C19	0.051 (2)	0.076 (3)	0.038 (2)	−0.002 (2)	0.0085 (17)	−0.001 (2)
C20	0.052 (2)	0.050 (2)	0.043 (2)	0.0035 (18)	0.0079 (18)	0.0073 (19)
C21	0.038 (2)	0.045 (2)	0.037 (2)	−0.0021 (17)	0.0030 (16)	−0.0001 (18)
C22	0.053 (2)	0.037 (2)	0.054 (3)	0.0071 (19)	0.009 (2)	0.002 (2)
C23	0.105 (3)	0.080 (3)	0.057 (3)	−0.009 (3)	0.032 (2)	0.016 (2)
C24	0.221 (5)	0.068 (3)	0.073 (3)	−0.017 (3)	0.054 (3)	0.007 (3)
C25	0.046 (2)	0.034 (2)	0.037 (2)	0.0016 (18)	0.0133 (16)	−0.0047 (17)
C26	0.061 (2)	0.042 (2)	0.058 (2)	−0.0007 (19)	0.0005 (19)	0.0012 (19)
C27	0.068 (3)	0.063 (3)	0.078 (3)	0.009 (2)	0.002 (2)	0.019 (2)
C28	0.080 (3)	0.044 (3)	0.101 (3)	0.012 (2)	0.038 (2)	0.024 (2)
C29	0.076 (3)	0.038 (2)	0.090 (3)	−0.013 (2)	0.040 (2)	−0.007 (2)
C30	0.055 (2)	0.048 (2)	0.063 (3)	−0.002 (2)	0.0141 (18)	−0.010 (2)

Cl1—C1	1.754 (3)	C20—C21	1.410 (5)
Cl2—C18	1.738 (3)	C23—C24	1.474 (5)
O1—C12	1.430 (3)	C25—C26	1.380 (5)
O1—C13	1.351 (4)	C25—C30	1.380 (4)
O2—C22	1.182 (4)	C26—C27	1.392 (5)
O3—C22	1.322 (4)	C27—C28	1.370 (5)
O3—C23	1.453 (4)	C28—C29	1.355 (5)
N1—C1	1.288 (4)	C29—C30	1.396 (5)
N1—C8	1.382 (4)	C3—H3	0.9300
N2—C13	1.293 (4)	C4—H4	0.9300
N2—C21	1.371 (4)	C5—H5	0.9300
C1—C2	1.418 (4)	C10—H10A	0.9600
C2—C3	1.356 (5)	C10—H10B	0.9600
C2—C12	1.501 (4)	C10—H10C	0.9600
C3—C9	1.406 (4)	C11—H11A	0.9600
C4—C5	1.354 (5)	C11—H11B	0.9600
C4—C9	1.415 (5)	C11—H11C	0.9600
C5—C6	1.411 (5)	C12—H12A	0.9700
C6—C7	1.368 (5)	C12—H12B	0.9700
C6—C11	1.524 (4)	C17—H17	0.9300
C7—C8	1.415 (4)	C19—H19	0.9300
C7—C10	1.509 (4)	C20—H20	0.9300
C8—C9	1.411 (4)	C23—H23A	0.9700
C13—C14	1.432 (4)	C23—H23B	0.9700
C14—C15	1.354 (4)	C24—H24A	0.9600
C14—C22	1.512 (5)	C24—H24B	0.9600
C15—C16	1.431 (5)	C24—H24C	0.9600
C15—C25	1.510 (4)	C26—H26	0.9300
C16—C17	1.409 (4)	C27—H27	0.9300
C16—C21	1.419 (4)	C28—H28	0.9300
C17—C18	1.355 (5)	C29—H29	0.9300
C18—C19	1.387 (5)	C30—H30	0.9300
C19—C20	1.365 (4)
C12—O1—C13	119.0 (2)	C26—C27—C28	121.3 (3)
C22—O3—C23	118.3 (2)	C27—C28—C29	119.2 (3)
C1—N1—C8	117.8 (2)	C28—C29—C30	121.1 (3)
C13—N2—C21	116.3 (3)	C25—C30—C29	119.4 (3)
Cl1—C1—N1	116.0 (2)	C2—C3—H3	120.00
Cl1—C1—C2	116.7 (2)	C9—C3—H3	119.00
N1—C1—C2	127.3 (3)	C5—C4—H4	120.00
C1—C2—C3	115.1 (3)	C9—C4—H4	120.00
C1—C2—C12	122.2 (3)	C4—C5—H5	119.00
C3—C2—C12	122.7 (3)	C6—C5—H5	119.00
C2—C3—C9	120.9 (3)	C7—C10—H10A	109.00
C5—C4—C9	120.4 (3)	C7—C10—H10B	109.00
C4—C5—C6	121.5 (3)	C7—C10—H10C	109.00
C5—C6—C7	120.3 (3)	H10A—C10—H10B	110.00
C5—C6—C11	117.6 (3)	H10A—C10—H10C	109.00
C7—C6—C11	122.1 (3)	H10B—C10—H10C	109.00
C6—C7—C8	118.5 (3)	C6—C11—H11A	109.00
C6—C7—C10	121.2 (3)	C6—C11—H11B	110.00
C8—C7—C10	120.3 (3)	C6—C11—H11C	109.00
N1—C8—C7	118.8 (3)	H11A—C11—H11B	109.00
N1—C8—C9	119.6 (3)	H11A—C11—H11C	110.00
C7—C8—C9	121.7 (3)	H11B—C11—H11C	109.00
C3—C9—C4	123.1 (3)	O1—C12—H12A	111.00
C3—C9—C8	119.3 (3)	O1—C12—H12B	110.00
C4—C9—C8	117.6 (3)	C2—C12—H12A	111.00
O1—C12—C2	106.1 (2)	C2—C12—H12B	111.00
O1—C13—N2	120.8 (3)	H12A—C12—H12B	109.00
O1—C13—C14	113.2 (3)	C16—C17—H17	120.00
N2—C13—C14	125.9 (3)	C18—C17—H17	120.00
C13—C14—C15	118.3 (3)	C18—C19—H19	120.00
C13—C14—C22	118.5 (3)	C20—C19—H19	120.00
C15—C14—C22	123.2 (3)	C19—C20—H20	119.00
C14—C15—C16	118.7 (3)	C21—C20—H20	119.00
C14—C15—C25	121.6 (3)	O3—C23—H23A	110.00
C16—C15—C25	119.7 (3)	O3—C23—H23B	110.00
C15—C16—C17	123.7 (3)	C24—C23—H23A	110.00
C15—C16—C21	117.7 (3)	C24—C23—H23B	110.00
C17—C16—C21	118.6 (3)	H23A—C23—H23B	108.00
C16—C17—C18	120.5 (3)	C23—C24—H24A	110.00
Cl2—C18—C17	119.4 (2)	C23—C24—H24B	109.00
Cl2—C18—C19	118.9 (3)	C23—C24—H24C	109.00
C17—C18—C19	121.6 (3)	H24A—C24—H24B	109.00
C18—C19—C20	119.4 (3)	H24A—C24—H24C	109.00
C19—C20—C21	121.2 (3)	H24B—C24—H24C	109.00
N2—C21—C16	123.1 (3)	C25—C26—H26	120.00
N2—C21—C20	118.2 (3)	C27—C26—H26	121.00
C16—C21—C20	118.6 (3)	C26—C27—H27	119.00
O2—C22—O3	125.8 (3)	C28—C27—H27	119.00
O2—C22—C14	125.7 (3)	C27—C28—H28	120.00
O3—C22—C14	108.5 (3)	C29—C28—H28	120.00
O3—C23—C24	108.1 (3)	C28—C29—H29	119.00
C15—C25—C26	119.6 (3)	C30—C29—H29	119.00
C15—C25—C30	120.5 (3)	C25—C30—H30	120.00
C26—C25—C30	119.9 (3)	C29—C30—H30	120.00
C25—C26—C27	119.1 (3)
C13—O1—C12—C2	−177.7 (2)	O1—C13—C14—C15	−178.0 (2)
C12—O1—C13—N2	−1.6 (4)	O1—C13—C14—C22	−1.4 (4)
C12—O1—C13—C14	175.3 (2)	N2—C13—C14—C15	−1.3 (4)
C23—O3—C22—O2	3.1 (5)	N2—C13—C14—C22	175.2 (3)
C23—O3—C22—C14	−177.2 (2)	C13—C14—C15—C16	0.0 (4)
C22—O3—C23—C24	113.9 (3)	C13—C14—C15—C25	179.0 (3)
C8—N1—C1—Cl1	−178.8 (2)	C22—C14—C15—C16	−176.3 (3)
C8—N1—C1—C2	−0.6 (4)	C22—C14—C15—C25	2.6 (4)
C1—N1—C8—C7	−177.9 (3)	C13—C14—C22—O2	64.1 (4)
C1—N1—C8—C9	2.6 (4)	C13—C14—C22—O3	−115.7 (3)
C21—N2—C13—O1	178.5 (2)	C15—C14—C22—O2	−119.6 (4)
C21—N2—C13—C14	2.0 (4)	C15—C14—C22—O3	60.7 (4)
C13—N2—C21—C16	−1.6 (4)	C14—C15—C16—C17	−179.4 (3)
C13—N2—C21—C20	−179.4 (3)	C14—C15—C16—C21	0.3 (4)
Cl1—C1—C2—C3	177.3 (2)	C25—C15—C16—C17	1.6 (4)
Cl1—C1—C2—C12	−4.5 (3)	C25—C15—C16—C21	−178.7 (3)
N1—C1—C2—C3	−0.9 (4)	C14—C15—C25—C26	70.0 (4)
N1—C1—C2—C12	177.4 (3)	C14—C15—C25—C30	−110.1 (4)
C1—C2—C3—C9	0.2 (4)	C16—C15—C25—C26	−111.1 (3)
C12—C2—C3—C9	−178.0 (2)	C16—C15—C25—C30	68.8 (4)
C1—C2—C12—O1	178.9 (2)	C15—C16—C17—C18	−178.1 (3)
C3—C2—C12—O1	−3.1 (3)	C21—C16—C17—C18	2.2 (4)
C2—C3—C9—C4	−179.7 (3)	C15—C16—C21—N2	0.5 (4)
C2—C3—C9—C8	1.7 (4)	C15—C16—C21—C20	178.3 (2)
C9—C4—C5—C6	0.1 (5)	C17—C16—C21—N2	−179.8 (3)
C5—C4—C9—C3	−178.1 (3)	C17—C16—C21—C20	−2.0 (4)
C5—C4—C9—C8	0.4 (4)	C16—C17—C18—Cl2	179.0 (2)
C4—C5—C6—C7	0.1 (5)	C16—C17—C18—C19	−1.2 (4)
C4—C5—C6—C11	179.6 (3)	Cl2—C18—C19—C20	179.7 (2)
C5—C6—C7—C8	−0.8 (4)	C17—C18—C19—C20	−0.1 (4)
C5—C6—C7—C10	178.4 (3)	C18—C19—C20—C21	0.3 (4)
C11—C6—C7—C8	179.7 (2)	C19—C20—C21—N2	178.7 (3)
C11—C6—C7—C10	−1.1 (4)	C19—C20—C21—C16	0.8 (4)
C6—C7—C8—N1	−178.0 (3)	C15—C25—C26—C27	178.6 (3)
C6—C7—C8—C9	1.5 (4)	C30—C25—C26—C27	−1.3 (5)
C10—C7—C8—N1	2.8 (4)	C15—C25—C30—C29	−178.9 (3)
C10—C7—C8—C9	−177.8 (2)	C26—C25—C30—C29	0.9 (5)
N1—C8—C9—C3	−3.2 (4)	C25—C26—C27—C28	0.9 (5)
N1—C8—C9—C4	178.2 (2)	C26—C27—C28—C29	−0.1 (5)
C7—C8—C9—C3	177.4 (3)	C27—C28—C29—C30	−0.2 (5)
C7—C8—C9—C4	−1.3 (4)	C28—C29—C30—C25	−0.2 (5)

Cg2, Cg3 and Cg5 are the centroids of the N2/C13–C16/C21, C4–C9 and C25–C30 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O2i	0.97	2.59	3.364 (3)	137
C26—H26···N1i	0.93	2.54	3.418 (4)	157
C10—H10C···Cg2ii	0.96	2.94	3.753 (3)	143
C12—H12B···Cg3ii	0.97	2.82	3.652 (3)	144
C24—H24B···Cg5iii	0.96	2.98	3.821 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg2, Cg3 and Cg5 are the centroids of the N2/C13–C16/C21, C4–C9 and C25–C30 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O2i	0.97	2.59	3.364 (3)	137
C26—H26⋯N1i	0.93	2.54	3.418 (4)	157
C10—H10C⋯Cg2ii	0.96	2.94	3.753 (3)	143
C12—H12B⋯Cg3ii	0.97	2.82	3.652 (3)	144
C24—H24B⋯Cg5iii	0.96	2.98	3.821 (4)	147

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