4,6-Dimethyl-2-(naphthalen-1-yl)pyrimidine.

The asymmetric unit of the title compound, C(16)H(14)N(2), contains two independent mol-ecules in which the dihedral angles between the pyrimidine and naphthaline rings are 38.20 (5) and 39.35 (5)°. Inter-molecular C-H⋯π contacts and π-π stacking inter-actions [centroid-centroid distances = 3.766 (1) and 3.792 (1) Å] are present in the crystal structure.

Related literature

For cyclo­metalated Ir(III) complexes, see: Chen et al. (2010 ▶); Talarico et al. (2010 ▶); Xu et al. (2011 ▶); Yang et al. (2006 ▶). For the synthesis, see: Wang et al. (2011 ▶).

Experimental

Crystal data

C16H14N2

M = 234.29

Monoclinic,

a = 14.9022 (18) Å

b = 11.4756 (14) Å

c = 15.9499 (19) Å

β = 111.028 (1)°

V = 2546.0 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.50 × 0.37 × 0.29 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.965, T max = 0.979

18638 measured reflections

4733 independent reflections

3442 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.129

S = 1.06

4733 reflections

329 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811027875/si2364sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027875/si2364Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027875/si2364Isup3.cml

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

C16H14N2	F(000) = 992
Mr = 234.29	Dx = 1.222 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.9022 (18) Å	Cell parameters from 5588 reflections
b = 11.4756 (14) Å	θ = 2.4–27.4°
c = 15.9499 (19) Å	µ = 0.07 mm−1
β = 111.028 (1)°	T = 296 K
V = 2546.0 (5) Å3	Block, colourless
Z = 8	0.50 × 0.37 × 0.29 mm

Bruker SMART APEX CCD area-detector diffractometer	4733 independent reflections
Radiation source: fine-focus sealed tube	3442 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.965, Tmax = 0.979	k = −13→13
18638 measured reflections	l = −19→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0523P)2 + 0.8594P] where P = (Fo2 + 2Fc2)/3
4733 reflections	(Δ/σ)max < 0.001
329 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.18 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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	0.33022 (12)	0.56804 (15)	0.19201 (11)	0.0391 (4)
C2	0.28518 (12)	0.54003 (15)	0.25537 (11)	0.0382 (4)
C3	0.31319 (13)	0.58798 (17)	0.34283 (12)	0.0466 (5)
H3	0.3632	0.6417	0.3614	0.056*
C4	0.26816 (14)	0.55681 (19)	0.40020 (13)	0.0545 (5)
H4	0.2882	0.5891	0.4575	0.065*
C5	0.19230 (15)	0.47692 (19)	0.37416 (14)	0.0574 (5)
H5	0.1631	0.4549	0.4144	0.069*
C6	0.16151 (14)	0.43166 (18)	0.29020 (14)	0.0535 (5)
H6	0.1102	0.3797	0.2729	0.064*
C7	0.20588 (12)	0.46173 (16)	0.22806 (12)	0.0429 (4)
C8	0.17279 (13)	0.41556 (17)	0.14022 (13)	0.0493 (5)
H8	0.1219	0.3630	0.1230	0.059*
C9	0.21425 (13)	0.44683 (17)	0.08061 (13)	0.0507 (5)
H9	0.1905	0.4175	0.0224	0.061*
C10	0.29303 (12)	0.52348 (16)	0.10659 (12)	0.0453 (4)
H10	0.3206	0.5445	0.0649	0.054*
C11	0.41918 (12)	0.63937 (15)	0.21483 (12)	0.0399 (4)
C12	0.50852 (13)	0.76663 (16)	0.16641 (13)	0.0466 (4)
C13	0.58104 (13)	0.75808 (17)	0.24906 (13)	0.0481 (5)
H13	0.6379	0.7995	0.2612	0.058*
C14	0.56827 (13)	0.68750 (16)	0.31349 (12)	0.0450 (4)
C15	0.51631 (16)	0.8421 (2)	0.09295 (15)	0.0643 (6)
H15A	0.4803	0.8079	0.0358	0.097*
H15B	0.5826	0.8489	0.0991	0.097*
H15C	0.4910	0.9180	0.0968	0.097*
C16	0.64365 (14)	0.67278 (19)	0.40496 (13)	0.0588 (5)
H16A	0.6343	0.7300	0.4450	0.088*
H16B	0.7061	0.6828	0.4014	0.088*
H16C	0.6388	0.5962	0.4271	0.088*
C17	0.12658 (11)	0.06318 (15)	0.19754 (11)	0.0357 (4)
C18	0.09762 (13)	0.01305 (17)	0.11404 (11)	0.0435 (4)
H18	0.0368	0.0304	0.0729	0.052*
C19	0.15642 (13)	−0.06341 (16)	0.08848 (12)	0.0454 (4)
H19	0.1345	−0.0962	0.0313	0.054*
C20	0.24584 (13)	−0.08964 (16)	0.14757 (12)	0.0440 (4)
H20	0.2842	−0.1420	0.1311	0.053*
C21	0.28081 (12)	−0.03786 (15)	0.23378 (11)	0.0381 (4)
C22	0.37491 (13)	−0.06205 (18)	0.29471 (13)	0.0501 (5)
H22	0.4136	−0.1140	0.2783	0.060*
C23	0.40930 (13)	−0.0107 (2)	0.37641 (13)	0.0561 (5)
H23	0.4709	−0.0283	0.4159	0.067*
C24	0.35244 (13)	0.06895 (18)	0.40169 (12)	0.0500 (5)
H24	0.3771	0.1048	0.4576	0.060*
C25	0.26154 (12)	0.09449 (16)	0.34545 (11)	0.0413 (4)
H25	0.2250	0.1479	0.3634	0.050*
C26	0.22168 (11)	0.04068 (14)	0.25978 (10)	0.0345 (4)
C27	0.05443 (11)	0.13401 (15)	0.21966 (11)	0.0360 (4)
C28	−0.01736 (12)	0.18418 (16)	0.31890 (12)	0.0425 (4)
C29	−0.08211 (12)	0.25082 (16)	0.25319 (12)	0.0432 (4)
H29	−0.1305	0.2911	0.2649	0.052*
C30	−0.07448 (12)	0.25720 (15)	0.16983 (12)	0.0407 (4)
C31	−0.02058 (15)	0.1730 (2)	0.41097 (13)	0.0608 (6)
H31A	0.0023	0.0973	0.4347	0.091*
H31B	−0.0855	0.1828	0.4082	0.091*
H31C	0.0195	0.2317	0.4493	0.091*
C32	−0.14053 (14)	0.33086 (18)	0.09602 (13)	0.0548 (5)
H32A	−0.1143	0.4079	0.0998	0.082*
H32B	−0.2023	0.3348	0.1019	0.082*
H32C	−0.1473	0.2971	0.0390	0.082*
N1	0.48627 (10)	0.62722 (13)	0.29660 (10)	0.0437 (4)
N2	0.42607 (10)	0.70672 (13)	0.14848 (10)	0.0443 (4)
N3	−0.00560 (10)	0.19787 (12)	0.15203 (9)	0.0395 (3)
N4	0.05243 (10)	0.12487 (13)	0.30227 (9)	0.0406 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0340 (9)	0.0402 (10)	0.0421 (10)	0.0027 (7)	0.0125 (7)	0.0004 (8)
C2	0.0324 (8)	0.0386 (10)	0.0423 (10)	0.0043 (7)	0.0119 (7)	0.0018 (7)
C3	0.0382 (9)	0.0543 (12)	0.0478 (11)	−0.0007 (8)	0.0160 (8)	−0.0062 (9)
C4	0.0525 (12)	0.0654 (13)	0.0480 (11)	0.0035 (10)	0.0212 (9)	−0.0036 (10)
C5	0.0562 (12)	0.0655 (14)	0.0593 (13)	−0.0010 (10)	0.0315 (10)	0.0055 (11)
C6	0.0465 (11)	0.0546 (12)	0.0631 (13)	−0.0071 (9)	0.0240 (10)	0.0014 (10)
C7	0.0358 (9)	0.0429 (10)	0.0493 (11)	0.0013 (8)	0.0145 (8)	0.0025 (8)
C8	0.0402 (10)	0.0505 (12)	0.0530 (11)	−0.0065 (8)	0.0118 (9)	−0.0033 (9)
C9	0.0485 (11)	0.0533 (12)	0.0447 (11)	−0.0035 (9)	0.0100 (9)	−0.0068 (9)
C10	0.0433 (10)	0.0496 (11)	0.0437 (10)	0.0003 (8)	0.0165 (8)	0.0014 (8)
C11	0.0382 (9)	0.0386 (10)	0.0453 (10)	0.0041 (7)	0.0178 (8)	−0.0016 (8)
C12	0.0456 (10)	0.0429 (11)	0.0573 (12)	0.0013 (8)	0.0257 (9)	−0.0002 (9)
C13	0.0406 (10)	0.0461 (11)	0.0606 (12)	−0.0068 (8)	0.0220 (9)	−0.0064 (9)
C14	0.0396 (9)	0.0449 (11)	0.0516 (11)	0.0005 (8)	0.0179 (8)	−0.0064 (9)
C15	0.0676 (14)	0.0621 (14)	0.0678 (14)	−0.0064 (11)	0.0298 (11)	0.0121 (11)
C16	0.0483 (11)	0.0662 (14)	0.0560 (12)	−0.0050 (10)	0.0115 (9)	−0.0046 (10)
C17	0.0349 (9)	0.0390 (9)	0.0348 (9)	0.0030 (7)	0.0143 (7)	0.0021 (7)
C18	0.0406 (9)	0.0518 (11)	0.0356 (9)	0.0068 (8)	0.0108 (8)	−0.0008 (8)
C19	0.0510 (11)	0.0490 (11)	0.0377 (10)	0.0040 (9)	0.0179 (8)	−0.0056 (8)
C20	0.0470 (10)	0.0450 (11)	0.0468 (10)	0.0067 (8)	0.0251 (8)	−0.0020 (8)
C21	0.0360 (9)	0.0390 (10)	0.0433 (10)	0.0033 (7)	0.0190 (8)	0.0053 (7)
C22	0.0404 (10)	0.0549 (12)	0.0557 (12)	0.0135 (9)	0.0182 (9)	0.0046 (9)
C23	0.0373 (10)	0.0699 (14)	0.0528 (12)	0.0095 (10)	0.0061 (9)	0.0055 (10)
C24	0.0425 (10)	0.0611 (13)	0.0412 (10)	−0.0032 (9)	0.0086 (8)	−0.0025 (9)
C25	0.0380 (9)	0.0453 (10)	0.0418 (10)	0.0000 (8)	0.0159 (8)	−0.0017 (8)
C26	0.0340 (8)	0.0365 (9)	0.0366 (9)	0.0012 (7)	0.0169 (7)	0.0035 (7)
C27	0.0333 (8)	0.0366 (9)	0.0375 (9)	0.0001 (7)	0.0121 (7)	−0.0011 (7)
C28	0.0379 (9)	0.0501 (11)	0.0412 (10)	0.0036 (8)	0.0163 (8)	−0.0003 (8)
C29	0.0380 (9)	0.0469 (11)	0.0458 (10)	0.0099 (8)	0.0165 (8)	−0.0017 (8)
C30	0.0381 (9)	0.0391 (10)	0.0435 (10)	0.0044 (8)	0.0129 (8)	−0.0002 (8)
C31	0.0629 (13)	0.0800 (16)	0.0458 (11)	0.0202 (11)	0.0271 (10)	0.0076 (10)
C32	0.0602 (12)	0.0546 (12)	0.0471 (11)	0.0209 (10)	0.0162 (9)	0.0075 (9)
N1	0.0383 (8)	0.0447 (9)	0.0482 (9)	−0.0011 (7)	0.0158 (7)	−0.0022 (7)
N2	0.0426 (8)	0.0431 (9)	0.0499 (9)	0.0018 (7)	0.0200 (7)	0.0003 (7)
N3	0.0381 (8)	0.0402 (8)	0.0399 (8)	0.0045 (6)	0.0136 (6)	0.0015 (6)
N4	0.0377 (8)	0.0465 (9)	0.0392 (8)	0.0066 (7)	0.0159 (6)	0.0019 (7)

C1—C10	1.372 (2)	C17—C18	1.371 (2)
C1—C2	1.436 (2)	C17—C26	1.432 (2)
C1—C11	1.488 (2)	C17—C27	1.488 (2)
C2—C3	1.416 (2)	C18—C19	1.400 (2)
C2—C7	1.423 (2)	C18—H18	0.9300
C3—C4	1.362 (3)	C19—C20	1.361 (2)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.398 (3)	C20—C21	1.415 (2)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.354 (3)	C21—C22	1.418 (2)
C5—H5	0.9300	C21—C26	1.422 (2)
C6—C7	1.417 (3)	C22—C23	1.353 (3)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.411 (3)	C23—C24	1.400 (3)
C8—C9	1.355 (3)	C23—H23	0.9300
C8—H8	0.9300	C24—C25	1.361 (2)
C9—C10	1.405 (3)	C24—H24	0.9300
C9—H9	0.9300	C25—C26	1.421 (2)
C10—H10	0.9300	C25—H25	0.9300
C11—N1	1.336 (2)	C27—N4	1.333 (2)
C11—N2	1.344 (2)	C27—N3	1.345 (2)
C12—N2	1.346 (2)	C28—N4	1.347 (2)
C12—C13	1.376 (3)	C28—C29	1.374 (2)
C12—C15	1.495 (3)	C28—C31	1.492 (2)
C13—C14	1.374 (3)	C29—C30	1.376 (2)
C13—H13	0.9300	C29—H29	0.9300
C14—N1	1.345 (2)	C30—N3	1.344 (2)
C14—C16	1.498 (3)	C30—C32	1.496 (2)
C15—H15A	0.9600	C31—H31A	0.9600
C15—H15B	0.9600	C31—H31B	0.9600
C15—H15C	0.9600	C31—H31C	0.9600
C16—H16A	0.9600	C32—H32A	0.9600
C16—H16B	0.9600	C32—H32B	0.9600
C16—H16C	0.9600	C32—H32C	0.9600
C10—C1—C2	119.41 (16)	C26—C17—C27	123.63 (14)
C10—C1—C11	117.06 (15)	C17—C18—C19	122.29 (16)
C2—C1—C11	123.47 (15)	C17—C18—H18	118.9
C3—C2—C7	117.77 (16)	C19—C18—H18	118.9
C3—C2—C1	124.01 (16)	C20—C19—C18	119.77 (16)
C7—C2—C1	118.20 (16)	C20—C19—H19	120.1
C4—C3—C2	121.16 (18)	C18—C19—H19	120.1
C4—C3—H3	119.4	C19—C20—C21	120.51 (16)
C2—C3—H3	119.4	C19—C20—H20	119.7
C3—C4—C5	120.89 (19)	C21—C20—H20	119.7
C3—C4—H4	119.6	C20—C21—C22	120.85 (16)
C5—C4—H4	119.6	C20—C21—C26	119.93 (15)
C6—C5—C4	119.76 (18)	C22—C21—C26	119.22 (16)
C6—C5—H5	120.1	C23—C22—C21	120.97 (17)
C4—C5—H5	120.1	C23—C22—H22	119.5
C5—C6—C7	121.38 (19)	C21—C22—H22	119.5
C5—C6—H6	119.3	C22—C23—C24	120.18 (17)
C7—C6—H6	119.3	C22—C23—H23	119.9
C8—C7—C6	121.22 (17)	C24—C23—H23	119.9
C8—C7—C2	119.81 (16)	C25—C24—C23	120.84 (18)
C6—C7—C2	118.97 (17)	C25—C24—H24	119.6
C9—C8—C7	120.82 (17)	C23—C24—H24	119.6
C9—C8—H8	119.6	C24—C25—C26	120.92 (17)
C7—C8—H8	119.6	C24—C25—H25	119.5
C8—C9—C10	120.13 (18)	C26—C25—H25	119.5
C8—C9—H9	119.9	C25—C26—C21	117.83 (15)
C10—C9—H9	119.9	C25—C26—C17	123.81 (15)
C1—C10—C9	121.54 (17)	C21—C26—C17	118.34 (15)
C1—C10—H10	119.2	N4—C27—N3	126.26 (15)
C9—C10—H10	119.2	N4—C27—C17	117.76 (14)
N1—C11—N2	125.94 (16)	N3—C27—C17	115.91 (14)
N1—C11—C1	118.07 (15)	N4—C28—C29	120.77 (16)
N2—C11—C1	115.91 (15)	N4—C28—C31	116.77 (16)
N2—C12—C13	120.69 (17)	C29—C28—C31	122.47 (16)
N2—C12—C15	116.82 (17)	C28—C29—C30	119.18 (16)
C13—C12—C15	122.50 (18)	C28—C29—H29	120.4
C14—C13—C12	119.12 (17)	C30—C29—H29	120.4
C14—C13—H13	120.4	N3—C30—C29	120.73 (16)
C12—C13—H13	120.4	N3—C30—C32	117.18 (16)
N1—C14—C13	120.87 (17)	C29—C30—C32	122.09 (16)
N1—C14—C16	116.57 (17)	C28—C31—H31A	109.5
C13—C14—C16	122.56 (17)	C28—C31—H31B	109.5
C12—C15—H15A	109.5	H31A—C31—H31B	109.5
C12—C15—H15B	109.5	C28—C31—H31C	109.5
H15A—C15—H15B	109.5	H31A—C31—H31C	109.5
C12—C15—H15C	109.5	H31B—C31—H31C	109.5
H15A—C15—H15C	109.5	C30—C32—H32A	109.5
H15B—C15—H15C	109.5	C30—C32—H32B	109.5
C14—C16—H16A	109.5	H32A—C32—H32B	109.5
C14—C16—H16B	109.5	C30—C32—H32C	109.5
H16A—C16—H16B	109.5	H32A—C32—H32C	109.5
C14—C16—H16C	109.5	H32B—C32—H32C	109.5
H16A—C16—H16C	109.5	C11—N1—C14	116.74 (15)
H16B—C16—H16C	109.5	C11—N2—C12	116.63 (15)
C18—C17—C26	119.09 (15)	C30—N3—C27	116.44 (14)
C18—C17—C27	117.21 (14)	C27—N4—C28	116.61 (14)
C10—C1—C2—C3	−175.15 (17)	C21—C22—C23—C24	−0.8 (3)
C11—C1—C2—C3	7.8 (3)	C22—C23—C24—C25	1.1 (3)
C10—C1—C2—C7	3.1 (2)	C23—C24—C25—C26	0.3 (3)
C11—C1—C2—C7	−173.91 (16)	C24—C25—C26—C21	−1.9 (3)
C7—C2—C3—C4	2.5 (3)	C24—C25—C26—C17	179.75 (17)
C1—C2—C3—C4	−179.26 (18)	C20—C21—C26—C25	−177.21 (15)
C2—C3—C4—C5	−0.4 (3)	C22—C21—C26—C25	2.0 (2)
C3—C4—C5—C6	−1.5 (3)	C20—C21—C26—C17	1.3 (2)
C4—C5—C6—C7	1.3 (3)	C22—C21—C26—C17	−179.48 (15)
C5—C6—C7—C8	−179.16 (19)	C18—C17—C26—C25	175.28 (16)
C5—C6—C7—C2	0.8 (3)	C27—C17—C26—C25	−7.9 (3)
C3—C2—C7—C8	177.34 (16)	C18—C17—C26—C21	−3.1 (2)
C1—C2—C7—C8	−1.0 (3)	C27—C17—C26—C21	173.76 (15)
C3—C2—C7—C6	−2.6 (3)	C18—C17—C27—N4	140.10 (17)
C1—C2—C7—C6	179.01 (16)	C26—C17—C27—N4	−36.8 (2)
C6—C7—C8—C9	178.50 (19)	C18—C17—C27—N3	−37.2 (2)
C2—C7—C8—C9	−1.5 (3)	C26—C17—C27—N3	145.92 (16)
C7—C8—C9—C10	1.9 (3)	N4—C28—C29—C30	−0.5 (3)
C2—C1—C10—C9	−2.8 (3)	C31—C28—C29—C30	179.84 (19)
C11—C1—C10—C9	174.40 (16)	C28—C29—C30—N3	1.0 (3)
C8—C9—C10—C1	0.3 (3)	C28—C29—C30—C32	−178.10 (17)
C10—C1—C11—N1	−140.99 (17)	N2—C11—N1—C14	−0.5 (3)
C2—C1—C11—N1	36.1 (2)	C1—C11—N1—C14	176.14 (15)
C10—C1—C11—N2	35.9 (2)	C13—C14—N1—C11	0.2 (2)
C2—C1—C11—N2	−146.97 (16)	C16—C14—N1—C11	−179.46 (16)
N2—C12—C13—C14	−0.1 (3)	N1—C11—N2—C12	0.4 (3)
C15—C12—C13—C14	179.50 (18)	C1—C11—N2—C12	−176.27 (15)
C12—C13—C14—N1	0.0 (3)	C13—C12—N2—C11	−0.1 (2)
C12—C13—C14—C16	179.70 (18)	C15—C12—N2—C11	−179.72 (17)
C26—C17—C18—C19	2.7 (3)	C29—C30—N3—C27	−0.5 (2)
C27—C17—C18—C19	−174.41 (17)	C32—C30—N3—C27	178.65 (16)
C17—C18—C19—C20	−0.2 (3)	N4—C27—N3—C30	−0.6 (3)
C18—C19—C20—C21	−1.7 (3)	C17—C27—N3—C30	176.45 (15)
C19—C20—C21—C22	−178.11 (18)	N3—C27—N4—C28	1.0 (3)
C19—C20—C21—C26	1.1 (3)	C17—C27—N4—C28	−175.97 (15)
C20—C21—C22—C23	178.51 (18)	C29—C28—N4—C27	−0.4 (3)
C26—C21—C22—C23	−0.7 (3)	C31—C28—N4—C27	179.27 (17)

Cg1, Cg2, Cg5 and Cg6 are the centroids of the N1/N2/C11–C14, C1/C2/C7–C10, N3/N4,C27–C30 and C17–C21/C26 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···Cg1i	0.93	2.74	3.651 (4)	167
C13—H13···Cg2ii	0.93	2.76	3.597 (4)	150
C6—H6···Cg5	0.93	2.75	3.665 (2)	168
C29—H29···Cg6iii	0.93	2.72	3.546 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg5 and Cg6 are the centroids of the N1/N2/C11–C14, C1/C2/C7–C10, N3/N4,C27–C30 and C17–C21/C26 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22⋯Cg1i	0.93	2.74	3.651 (4)	167
C13—H13⋯Cg2ii	0.93	2.76	3.597 (4)	150
C6—H6⋯Cg5	0.93	2.75	3.665 (2)	168
C29—H29⋯Cg6iii	0.93	2.72	3.546 (3)	149

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