N (1),N (4)-Diphenyl-3,6-bis-(phenyl-imino)-cyclo-hexa-1,4-diene-1,4-di-amine.

In the title compound, C30H24N4, the central benzo-quinonedi-imine moiety is approximately planar, with a maximum deviation of 0.044 (14) Å. The four terminal phenyl rings are twisted by 44.95 (11), 54.90 (10), 44.98 (10) and 50.68 (11)° with respect to the mean plane the benzo-quinonedi-imine unit. In the crystal, mol-ecules are linked by weak C-H⋯π inter-actions into supra-molecular chains running along the b-axis direction.

Related literature

For general background to the title compound, see: Kimish (1875 ▶); Rall et al. (1998 ▶); Frantz et al. (2004 ▶); Siri et al. (2005 ▶); Taquet et al. (2006 ▶); Schweinfurth et al. (2013 ▶); Jeon et al. (2013 ▶). For related structures, see: Hughes & Saunders (1956 ▶); Merchant et al. (1984 ▶); Siri & Braunstein (2000 ▶); Wenderski et al. (2004 ▶); Khramov et al. (2006 ▶); Boydston et al. (2006 ▶); Huang et al., (2008 ▶); Su et al. (2012 ▶).

Experimental

Crystal data

C30H24N4

M = 440.53

Triclinic,

a = 8.8858 (12) Å

b = 10.0540 (13) Å

c = 13.2256 (18) Å

α = 93.343 (3)°

β = 106.760 (3)°

γ = 98.530 (3)°

V = 1112.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.977, T max = 0.992

8166 measured reflections

5291 independent reflections

3273 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.172

S = 1.03

5291 reflections

315 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814002906/xu5766sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002906/xu5766Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002906/xu5766Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C30H24N4	Z = 2
Mr = 440.53	F(000) = 464
Triclinic, P1	Dx = 1.315 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8858 (12) Å	Cell parameters from 1264 reflections
b = 10.0540 (13) Å	θ = 2.4–25.9°
c = 13.2256 (18) Å	µ = 0.08 mm−1
α = 93.343 (3)°	T = 173 K
β = 106.760 (3)°	Plate, red
γ = 98.530 (3)°	0.30 × 0.20 × 0.10 mm
V = 1112.4 (3) Å3

Bruker SMART APEX CCD area-detector diffractometer	5291 independent reflections
Radiation source: fine-focus sealed tube	3273 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 8.366 pixels mm-1	θmax = 28.0°, θmin = 1.6°
φ and ω scans	h = −10→11
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −12→13
Tmin = 0.977, Tmax = 0.992	l = −17→8
8166 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0775P)2 + 0.0548P] where P = (Fo2 + 2Fc2)/3
5291 reflections	(Δ/σ)max < 0.001
315 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.24 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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)5.6034 (0.0038) x + 5.0416 (0.0058) y + 12.9434 (0.0071) z = 8.2491 (0.0021)* 0.0006 (0.0008) C10 * -0.0066 (0.0008) C11 * 0.0067 (0.0009) C12 * -0.0008 (0.0009) C13 * -0.0053 (0.0009) C14 * 0.0053 (0.0008) C15Rms deviation of fitted atoms = 0.0049- 7.4963 (0.0028) x + 1.7481 (0.0065) y + 10.6592 (0.0082) z = 4.5261 (0.0067)Angle to previous plane (with approximate e.s.d.) = 86.71 (0.03)* 0.0118 (0.0008) C4 * -0.0134 (0.0008) C5 * 0.0021 (0.0009) C6 * 0.0111 (0.0009) C7 * -0.0128 (0.0009) C8 * 0.0013 (0.0009) C9Rms deviation of fitted atoms = 0.0101- 4.5932 (0.0050) x + 6.9089 (0.0064) y + 12.6394 (0.0086) z = 6.3197 (0.0043)Angle to previous plane (with approximate e.s.d.) = 30.79 (0.06)* 0.0005 (0.0006) C1 * -0.0005 (0.0006) C2 * 0.0005 (0.0006) C3 * -0.0005 (0.0006) C1_$1 * 0.0005 (0.0006) C2_$1 * -0.0005 (0.0006) C3_$1 - 3.3572 (0.0015) C13_$2 - 3.6100 (0.0013) C14_$2 - 3.7830 (0.0014) C15_$2Rms deviation of fitted atoms = 0.0005- 4.5932 (0.0050) x + 6.9089 (0.0064) y + 12.6394 (0.0086) z = 6.3197 (0.0043)Angle to previous plane (with approximate e.s.d.) = 0.00 (0.10)* 0.0005 (0.0006) C1 * -0.0005 (0.0006) C2 * 0.0005 (0.0006) C3 * -0.0005 (0.0006) C1_$1 * 0.0005 (0.0006) C2_$1 * -0.0005 (0.0006) C3_$1 - 3.7228 (0.0017) C10_$2 - 3.4796 (0.0019) C11_$2 - 3.2849 (0.0018) C12_$2Rms deviation of fitted atoms = 0.0005- 5.6034 (0.0038) x + 5.0416 (0.0058) y + 12.9434 (0.0070) z = 2.9266 (0.0041)Angle to previous plane (with approximate e.s.d.) = 10.70 (0.08)* 0.0006 (0.0008) C10_$2 * -0.0066 (0.0008) C11_$2 * 0.0067 (0.0009) C12_$2 * -0.0008 (0.0009) C13_$2 * -0.0053 (0.0009) C14_$2 * 0.0053 (0.0008) C15_$2Rms deviation of fitted atoms = 0.0049- 4.5932 (0.0050) x + 6.9089 (0.0064) y + 12.6394 (0.0086) z = 6.3197 (0.0043)Angle to previous plane (with approximate e.s.d.) = 10.70 (0.08)* 0.0005 (0.0006) C1 * -0.0005 (0.0006) C2 * 0.0005 (0.0006) C3 * -0.0005 (0.0006) C1_$1 * 0.0005 (0.0006) C2_$1 * -0.0005 (0.0006) C3_$1Rms deviation of fitted atoms = 0.0005

	x	y	z	Uiso*/Ueq
C1	0.6215 (2)	0.1790 (2)	0.48956 (16)	0.0279 (5)
C2	0.5987 (2)	0.2013 (2)	0.59667 (16)	0.0272 (5)
C3	0.4786 (3)	0.2780 (2)	0.60555 (17)	0.0291 (5)
H3	0.4665	0.2981	0.6736	0.035*
C4	0.3815 (3)	0.3228 (2)	0.51985 (17)	0.0290 (5)
C5	0.3993 (2)	0.2946 (2)	0.41226 (16)	0.0272 (5)
C6	0.5248 (3)	0.2248 (2)	0.40391 (17)	0.0298 (5)
H6	0.5412	0.2100	0.3366	0.036*
C7	0.8056 (2)	0.0811 (2)	0.40583 (17)	0.0305 (5)
C8	0.8318 (3)	0.1764 (2)	0.33796 (17)	0.0340 (5)
H8	0.8037	0.2632	0.3456	0.041*
C9	0.8982 (3)	0.1449 (2)	0.26007 (18)	0.0377 (6)
H9	0.9168	0.2109	0.2144	0.045*
C10	0.9386 (3)	0.0192 (2)	0.24679 (19)	0.0392 (6)
H10	0.9830	−0.0019	0.1918	0.047*
C11	0.9138 (3)	−0.0753 (2)	0.31417 (19)	0.0368 (6)
H11	0.9405	−0.1624	0.3054	0.044*
C12	0.8501 (3)	−0.0439 (2)	0.39462 (18)	0.0336 (5)
H12	0.8368	−0.1084	0.4424	0.040*
C13	0.6813 (3)	0.1632 (2)	0.77728 (16)	0.0286 (5)
C14	0.5421 (3)	0.1153 (2)	0.80110 (18)	0.0340 (5)
H14	0.4491	0.0748	0.7456	0.041*
C15	0.5379 (3)	0.1259 (2)	0.90426 (19)	0.0400 (6)
H15	0.4413	0.0938	0.9191	0.048*
C16	0.6711 (3)	0.1823 (2)	0.98623 (19)	0.0396 (6)
H16	0.6666	0.1908	1.0572	0.048*
C17	0.8115 (3)	0.2265 (2)	0.96395 (18)	0.0381 (6)
H17	0.9048	0.2642	1.0202	0.046*
C18	0.8180 (3)	0.2163 (2)	0.86100 (17)	0.0339 (5)
H18	0.9159	0.2457	0.8469	0.041*
C19	0.2077 (3)	0.4243 (2)	0.60850 (18)	0.0324 (5)
C20	0.3155 (3)	0.4832 (2)	0.70564 (19)	0.0386 (6)
H20	0.4267	0.5000	0.7138	0.046*
C21	0.2614 (3)	0.5167 (2)	0.78905 (19)	0.0399 (6)
H21	0.3360	0.5538	0.8555	0.048*
C22	0.1014 (3)	0.4976 (2)	0.77844 (19)	0.0411 (6)
H22	0.0655	0.5217	0.8369	0.049*
C23	−0.0066 (3)	0.4433 (2)	0.68263 (19)	0.0373 (6)
H23	−0.1176	0.4322	0.6745	0.045*
C24	0.0450 (3)	0.4049 (2)	0.59809 (19)	0.0352 (5)
H24	−0.0305	0.3651	0.5327	0.042*
C25	0.2863 (2)	0.3163 (2)	0.22856 (17)	0.0284 (5)
C26	0.2740 (3)	0.1896 (2)	0.17692 (18)	0.0344 (5)
H26	0.2778	0.1129	0.2157	0.041*
C27	0.2564 (3)	0.1740 (3)	0.06994 (19)	0.0426 (6)
H27	0.2469	0.0863	0.0354	0.051*
C28	0.2524 (3)	0.2840 (3)	0.01207 (19)	0.0447 (6)
H28	0.2436	0.2729	−0.0613	0.054*
C29	0.2612 (3)	0.4105 (3)	0.06249 (19)	0.0401 (6)
H29	0.2575	0.4867	0.0232	0.048*
C30	0.2753 (3)	0.4270 (2)	0.16866 (17)	0.0327 (5)
H30	0.2777	0.5139	0.2019	0.039*
H1	0.777 (3)	0.075 (3)	0.551 (2)	0.049 (8)*
H2	0.197 (3)	0.394 (3)	0.453 (2)	0.057 (8)*
N1	0.7414 (2)	0.1088 (2)	0.48930 (15)	0.0334 (5)
N2	0.6936 (2)	0.15137 (18)	0.67317 (14)	0.0296 (4)
N3	0.2589 (2)	0.3886 (2)	0.52080 (15)	0.0361 (5)
N4	0.2966 (2)	0.34011 (18)	0.33658 (14)	0.0300 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0257 (11)	0.0305 (12)	0.0276 (11)	0.0063 (9)	0.0076 (9)	0.0019 (9)
C2	0.0260 (11)	0.0272 (11)	0.0268 (11)	0.0027 (9)	0.0064 (9)	0.0036 (9)
C3	0.0331 (12)	0.0324 (12)	0.0248 (11)	0.0103 (9)	0.0111 (9)	0.0036 (9)
C4	0.0299 (11)	0.0301 (12)	0.0297 (12)	0.0090 (9)	0.0108 (9)	0.0046 (9)
C5	0.0267 (11)	0.0277 (11)	0.0262 (11)	0.0043 (9)	0.0064 (9)	0.0053 (9)
C6	0.0302 (12)	0.0367 (13)	0.0238 (11)	0.0081 (9)	0.0087 (9)	0.0042 (9)
C7	0.0223 (11)	0.0398 (13)	0.0277 (11)	0.0074 (9)	0.0037 (9)	0.0035 (10)
C8	0.0327 (12)	0.0338 (13)	0.0340 (13)	0.0082 (10)	0.0060 (10)	0.0058 (10)
C9	0.0393 (13)	0.0411 (14)	0.0336 (13)	0.0088 (11)	0.0108 (10)	0.0070 (11)
C10	0.0383 (14)	0.0460 (15)	0.0375 (13)	0.0119 (11)	0.0163 (11)	0.0020 (11)
C11	0.0336 (13)	0.0325 (13)	0.0443 (14)	0.0100 (10)	0.0104 (11)	0.0005 (11)
C12	0.0250 (11)	0.0352 (13)	0.0377 (13)	0.0063 (9)	0.0042 (9)	0.0066 (10)
C13	0.0326 (12)	0.0269 (11)	0.0273 (12)	0.0129 (9)	0.0059 (9)	0.0068 (9)
C14	0.0286 (12)	0.0384 (13)	0.0326 (13)	0.0077 (10)	0.0039 (9)	0.0072 (10)
C15	0.0387 (14)	0.0473 (15)	0.0390 (14)	0.0117 (11)	0.0159 (11)	0.0127 (12)
C16	0.0507 (16)	0.0438 (14)	0.0272 (12)	0.0126 (12)	0.0136 (11)	0.0047 (11)
C17	0.0424 (14)	0.0383 (14)	0.0282 (12)	0.0047 (11)	0.0036 (10)	0.0010 (10)
C18	0.0331 (12)	0.0317 (12)	0.0343 (13)	0.0040 (10)	0.0067 (10)	0.0056 (10)
C19	0.0375 (13)	0.0299 (12)	0.0332 (12)	0.0106 (10)	0.0126 (10)	0.0082 (10)
C20	0.0344 (13)	0.0398 (14)	0.0403 (14)	0.0075 (11)	0.0080 (11)	0.0078 (11)
C21	0.0470 (15)	0.0392 (14)	0.0313 (13)	0.0135 (11)	0.0058 (11)	−0.0002 (11)
C22	0.0554 (17)	0.0390 (14)	0.0350 (14)	0.0135 (12)	0.0201 (12)	0.0060 (11)
C23	0.0391 (13)	0.0354 (13)	0.0445 (14)	0.0117 (10)	0.0196 (11)	0.0108 (11)
C24	0.0350 (13)	0.0337 (13)	0.0356 (13)	0.0082 (10)	0.0071 (10)	0.0066 (10)
C25	0.0220 (10)	0.0360 (13)	0.0271 (11)	0.0080 (9)	0.0058 (9)	0.0040 (10)
C26	0.0336 (12)	0.0318 (12)	0.0367 (13)	0.0095 (10)	0.0069 (10)	0.0053 (10)
C27	0.0419 (15)	0.0423 (15)	0.0397 (14)	0.0115 (11)	0.0061 (11)	−0.0066 (12)
C28	0.0493 (16)	0.0602 (18)	0.0269 (13)	0.0211 (13)	0.0095 (11)	0.0040 (12)
C29	0.0467 (15)	0.0441 (15)	0.0314 (13)	0.0148 (12)	0.0097 (11)	0.0120 (11)
C30	0.0329 (12)	0.0326 (12)	0.0326 (12)	0.0096 (10)	0.0074 (10)	0.0049 (10)
N1	0.0346 (11)	0.0441 (12)	0.0255 (10)	0.0177 (9)	0.0088 (8)	0.0089 (9)
N2	0.0285 (10)	0.0336 (10)	0.0264 (10)	0.0091 (8)	0.0059 (8)	0.0038 (8)
N3	0.0407 (12)	0.0476 (12)	0.0264 (11)	0.0233 (9)	0.0111 (9)	0.0085 (9)
N4	0.0299 (10)	0.0336 (10)	0.0275 (10)	0.0091 (8)	0.0075 (8)	0.0074 (8)

C1—C6	1.360 (3)	C16—C17	1.380 (3)
C1—N1	1.363 (3)	C16—H16	0.9500
C1—C2	1.497 (3)	C17—C18	1.378 (3)
C2—N2	1.296 (3)	C17—H17	0.9500
C2—C3	1.433 (3)	C18—H18	0.9500
C3—C4	1.358 (3)	C19—C24	1.395 (3)
C3—H3	0.9500	C19—C20	1.397 (3)
C4—N3	1.358 (3)	C19—N3	1.409 (3)
C4—C5	1.492 (3)	C20—C21	1.368 (3)
C5—N4	1.302 (3)	C20—H20	0.9500
C5—C6	1.429 (3)	C21—C22	1.370 (3)
C6—H6	0.9500	C21—H21	0.9500
C7—C12	1.385 (3)	C22—C23	1.374 (4)
C7—C8	1.390 (3)	C22—H22	0.9500
C7—N1	1.412 (3)	C23—C24	1.381 (3)
C8—C9	1.370 (3)	C23—H23	0.9500
C8—H8	0.9500	C24—H24	0.9500
C9—C10	1.379 (3)	C25—C26	1.384 (3)
C9—H9	0.9500	C25—C30	1.402 (3)
C10—C11	1.377 (3)	C25—N4	1.409 (3)
C10—H10	0.9500	C26—C27	1.375 (3)
C11—C12	1.383 (3)	C26—H26	0.9500
C11—H11	0.9500	C27—C28	1.380 (3)
C12—H12	0.9500	C27—H27	0.9500
C13—C14	1.388 (3)	C28—C29	1.382 (4)
C13—C18	1.396 (3)	C28—H28	0.9500
C13—N2	1.412 (3)	C29—C30	1.371 (3)
C14—C15	1.374 (3)	C29—H29	0.9500
C14—H14	0.9500	C30—H30	0.9500
C15—C16	1.374 (3)	N1—H1	0.89 (3)
C15—H15	0.9500	N3—H2	0.91 (3)
C6—C1—N1	126.3 (2)	C18—C17—H17	119.6
C6—C1—C2	120.17 (19)	C16—C17—H17	119.6
N1—C1—C2	113.47 (17)	C17—C18—C13	120.3 (2)
N2—C2—C3	126.4 (2)	C17—C18—H18	119.8
N2—C2—C1	116.00 (19)	C13—C18—H18	119.8
C3—C2—C1	117.54 (18)	C24—C19—C20	118.5 (2)
C4—C3—C2	122.1 (2)	C24—C19—N3	119.7 (2)
C4—C3—H3	118.9	C20—C19—N3	121.8 (2)
C2—C3—H3	118.9	C21—C20—C19	120.1 (2)
N3—C4—C3	125.5 (2)	C21—C20—H20	119.9
N3—C4—C5	114.23 (18)	C19—C20—H20	119.9
C3—C4—C5	120.15 (19)	C20—C21—C22	121.1 (2)
N4—C5—C6	128.0 (2)	C20—C21—H21	119.4
N4—C5—C4	114.12 (19)	C22—C21—H21	119.4
C6—C5—C4	117.92 (18)	C21—C22—C23	119.5 (2)
C1—C6—C5	121.9 (2)	C21—C22—H22	120.2
C1—C6—H6	119.0	C23—C22—H22	120.2
C5—C6—H6	119.0	C22—C23—C24	120.5 (2)
C12—C7—C8	119.1 (2)	C22—C23—H23	119.7
C12—C7—N1	118.3 (2)	C24—C23—H23	119.7
C8—C7—N1	122.5 (2)	C23—C24—C19	120.1 (2)
C9—C8—C7	119.9 (2)	C23—C24—H24	119.9
C9—C8—H8	120.0	C19—C24—H24	119.9
C7—C8—H8	120.0	C26—C25—C30	118.5 (2)
C8—C9—C10	121.1 (2)	C26—C25—N4	124.02 (19)
C8—C9—H9	119.4	C30—C25—N4	117.3 (2)
C10—C9—H9	119.4	C27—C26—C25	120.4 (2)
C11—C10—C9	119.2 (2)	C27—C26—H26	119.8
C11—C10—H10	120.4	C25—C26—H26	119.8
C9—C10—H10	120.4	C26—C27—C28	120.9 (2)
C10—C11—C12	120.2 (2)	C26—C27—H27	119.5
C10—C11—H11	119.9	C28—C27—H27	119.5
C12—C11—H11	119.9	C27—C28—C29	119.0 (2)
C11—C12—C7	120.3 (2)	C27—C28—H28	120.5
C11—C12—H12	119.8	C29—C28—H28	120.5
C7—C12—H12	119.8	C30—C29—C28	120.6 (2)
C14—C13—C18	118.3 (2)	C30—C29—H29	119.7
C14—C13—N2	122.83 (19)	C28—C29—H29	119.7
C18—C13—N2	118.66 (19)	C29—C30—C25	120.4 (2)
C15—C14—C13	120.5 (2)	C29—C30—H30	119.8
C15—C14—H14	119.7	C25—C30—H30	119.8
C13—C14—H14	119.7	C1—N1—C7	128.76 (19)
C16—C15—C14	121.0 (2)	C1—N1—H1	111.5 (17)
C16—C15—H15	119.5	C7—N1—H1	119.7 (17)
C14—C15—H15	119.5	C2—N2—C13	121.28 (19)
C15—C16—C17	119.0 (2)	C4—N3—C19	127.73 (19)
C15—C16—H16	120.5	C4—N3—H2	110.8 (18)
C17—C16—H16	120.5	C19—N3—H2	120.5 (18)
C18—C17—C16	120.7 (2)	C5—N4—C25	123.01 (19)
C6—C1—C2—N2	178.4 (2)	C24—C19—C20—C21	2.0 (3)
N1—C1—C2—N2	−0.2 (3)	N3—C19—C20—C21	179.9 (2)
C6—C1—C2—C3	−3.3 (3)	C19—C20—C21—C22	−2.2 (4)
N1—C1—C2—C3	178.05 (19)	C20—C21—C22—C23	0.3 (4)
N2—C2—C3—C4	−178.1 (2)	C21—C22—C23—C24	1.7 (3)
C1—C2—C3—C4	3.8 (3)	C22—C23—C24—C19	−1.8 (3)
C2—C3—C4—N3	175.7 (2)	C20—C19—C24—C23	−0.1 (3)
C2—C3—C4—C5	−0.9 (3)	N3—C19—C24—C23	−178.0 (2)
N3—C4—C5—N4	1.4 (3)	C30—C25—C26—C27	2.0 (3)
C3—C4—C5—N4	178.4 (2)	N4—C25—C26—C27	176.7 (2)
N3—C4—C5—C6	−179.6 (2)	C25—C26—C27—C28	0.7 (4)
C3—C4—C5—C6	−2.6 (3)	C26—C27—C28—C29	−2.0 (4)
N1—C1—C6—C5	178.3 (2)	C27—C28—C29—C30	0.6 (4)
C2—C1—C6—C5	−0.1 (3)	C28—C29—C30—C25	2.1 (4)
N4—C5—C6—C1	−178.1 (2)	C26—C25—C30—C29	−3.4 (3)
C4—C5—C6—C1	3.1 (3)	N4—C25—C30—C29	−178.5 (2)
C12—C7—C8—C9	1.2 (3)	C6—C1—N1—C7	8.2 (4)
N1—C7—C8—C9	178.3 (2)	C2—C1—N1—C7	−173.3 (2)
C7—C8—C9—C10	0.6 (3)	C12—C7—N1—C1	−142.5 (2)
C8—C9—C10—C11	−1.0 (4)	C8—C7—N1—C1	40.4 (3)
C9—C10—C11—C12	−0.4 (3)	C3—C2—N2—C13	3.3 (3)
C10—C11—C12—C7	2.2 (3)	C1—C2—N2—C13	−178.59 (18)
C8—C7—C12—C11	−2.6 (3)	C14—C13—N2—C2	57.2 (3)
N1—C7—C12—C11	−179.8 (2)	C18—C13—N2—C2	−127.5 (2)
C18—C13—C14—C15	2.9 (3)	C3—C4—N3—C19	0.3 (4)
N2—C13—C14—C15	178.2 (2)	C5—C4—N3—C19	177.2 (2)
C13—C14—C15—C16	−0.8 (4)	C24—C19—N3—C4	−136.7 (2)
C14—C15—C16—C17	−1.2 (4)	C20—C19—N3—C4	45.4 (3)
C15—C16—C17—C18	1.0 (4)	C6—C5—N4—C25	5.4 (3)
C16—C17—C18—C13	1.1 (3)	C4—C5—N4—C25	−175.67 (18)
C14—C13—C18—C17	−3.0 (3)	C26—C25—N4—C5	51.4 (3)
N2—C13—C18—C17	−178.5 (2)	C30—C25—N4—C5	−133.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg4i	0.95	2.84	3.675 (2)	148
C14—H14···Cg2ii	0.95	2.81	3.673 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the C7–C12 and C19–C24 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cg4i	0.95	2.84	3.675 (2)	148
C14—H14⋯Cg2ii	0.95	2.81	3.673 (3)	151

Symmetry codes: (i) ; (ii) .