5-Phenyl-2-(4-pyrid-yl)pyrimidine.

The title compound, C(15)H(11)N(3), crystallizes with two independent mol-ecules in the asymmetric unit. The dihedral angles between the phenyl and pyridine rings in each mol-ecule are 53.48 (5) and 50.80 (5)°. In the crystal structure, weak inter-molecular C-H⋯N hydrogen bonds connect mol-ecules into one-dimensional chains. In addition, the crystal structure is stabilized by weak C-H⋯π(arene) inter-actions.

Related literature

For related literature, see: Fang et al. (2002 ▶, 2007 ▶); Medlycott & Hanan (2005 ▶, 2006 ▶); Spek (2003 ▶).

Experimental

Crystal data

C15H11N3

M = 233.27

Triclinic,

a = 9.2813 (5) Å

b = 9.3609 (5) Å

c = 13.9001 (7) Å

α = 71.462 (2)°

β = 86.957 (2)°

γ = 75.788 (3)°

V = 1109.54 (10) Å3

Z = 4

Cu Kα radiation

μ = 0.68 mm−1

T = 100 (2) K

0.40 × 0.38 × 0.08 mm

Data collection

Bruker SMART 6000 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.734, T max = 0.947

15167 measured reflections

3967 independent reflections

3226 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.139

S = 1.00

3967 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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: UdMX (local program).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800398X/lh2593sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800398X/lh2593Isup2.hkl

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

C15H11N3	Z = 4
Mr = 233.27	F(000) = 488
Triclinic, P1	Dx = 1.396 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 9.2813 (5) Å	Cell parameters from 5655 reflections
b = 9.3609 (5) Å	θ = 3.4–68.9°
c = 13.9001 (7) Å	µ = 0.68 mm−1
α = 71.462 (2)°	T = 100 K
β = 86.957 (2)°	Block, colourless
γ = 75.788 (3)°	0.40 × 0.38 × 0.08 mm
V = 1109.54 (10) Å3

Bruker SMART 6000 diffractometer	3967 independent reflections
Radiation source: Rotating anode	3226 reflections with I > 2σ(I)
Montel 200 optics	Rint = 0.046
Detector resolution: 5.5 pixels mm-1	θmax = 68.9°, θmin = 3.4°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
Tmin = 0.734, Tmax = 0.947	l = −16→16
15167 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0925P)2 + 0.1892P] where P = (Fo2 + 2Fc2)/3
3967 reflections	(Δ/σ)max = 0.001
325 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.30 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
N1	−0.09769 (12)	0.44347 (13)	1.42209 (9)	0.0235 (3)
N2	−0.12326 (12)	0.79515 (13)	1.05916 (8)	0.0215 (3)
N3	0.10382 (12)	0.60327 (13)	1.06789 (9)	0.0230 (3)
C28	0.60351 (14)	1.04795 (15)	0.59991 (10)	0.0230 (3)
H28	0.6235	1.0980	0.5313	0.028*
C24	0.59612 (14)	0.67217 (15)	0.96148 (10)	0.0211 (3)
H24	0.6697	0.6196	0.9262	0.025*
C22	0.40977 (14)	0.89133 (15)	0.96659 (10)	0.0210 (3)
H22	0.3519	0.9935	0.9349	0.025*
C1	−0.20867 (14)	0.54005 (15)	1.35782 (10)	0.0222 (3)
H1	−0.3061	0.5581	1.3835	0.027*
C2	−0.18962 (14)	0.61497 (15)	1.25624 (10)	0.0206 (3)
H2	−0.2717	0.6841	1.2144	0.025*
C3	−0.04783 (14)	0.58719 (14)	1.21624 (10)	0.0188 (3)
C4	0.06828 (14)	0.48702 (15)	1.28198 (10)	0.0204 (3)
H4	0.1664	0.4647	1.2580	0.025*
C5	0.03846 (14)	0.42042 (15)	1.38280 (10)	0.0218 (3)
H5	0.1193	0.3543	1.4270	0.026*
C6	−0.02146 (13)	0.66572 (15)	1.10832 (10)	0.0190 (3)
C7	−0.09684 (14)	0.86669 (15)	0.96277 (10)	0.0207 (3)
H7	−0.1671	0.9585	0.9265	0.025*
C8	0.02937 (13)	0.81303 (14)	0.91253 (10)	0.0191 (3)
C9	0.12654 (14)	0.67759 (15)	0.97125 (10)	0.0224 (3)
H9	0.2138	0.6359	0.9407	0.027*
C10	0.05403 (13)	0.89220 (15)	0.80502 (10)	0.0192 (3)
C11	0.00409 (13)	1.05394 (15)	0.76275 (10)	0.0203 (3)
H11	−0.0429	1.1139	0.8045	0.024*
C12	0.02259 (14)	1.12719 (15)	0.66058 (10)	0.0217 (3)
H12	−0.0111	1.2368	0.6330	0.026*
C13	0.09030 (14)	1.04032 (16)	0.59868 (10)	0.0223 (3)
H13	0.1021	1.0903	0.5287	0.027*
C14	0.14063 (14)	0.88000 (15)	0.63960 (10)	0.0227 (3)
H14	0.1872	0.8206	0.5974	0.027*
C15	0.12309 (13)	0.80658 (15)	0.74159 (10)	0.0202 (3)
H15	0.1582	0.6971	0.7689	0.024*
C29	0.71673 (14)	0.94102 (15)	0.66453 (10)	0.0221 (3)
H29	0.8144	0.9178	0.6400	0.027*
C30	0.68821 (13)	0.86809 (15)	0.76430 (10)	0.0197 (3)
H30	0.7664	0.7944	0.8077	0.024*
C25	0.54460 (14)	0.90173 (15)	0.80227 (10)	0.0186 (3)
C26	0.43120 (14)	1.00916 (15)	0.73613 (10)	0.0203 (3)
H26	0.3332	1.0326	0.7601	0.024*
C27	0.46033 (15)	1.08163 (15)	0.63604 (10)	0.0230 (3)
H27	0.3825	1.1545	0.5919	0.028*
C23	0.51637 (13)	0.82266 (15)	0.90904 (10)	0.0184 (3)
N6	0.57446 (11)	0.59835 (13)	1.05838 (8)	0.0210 (3)
C21	0.46901 (13)	0.67626 (15)	1.10567 (10)	0.0187 (3)
N5	0.38525 (12)	0.82082 (12)	1.06340 (8)	0.0211 (3)
C18	0.44441 (13)	0.59364 (15)	1.21314 (10)	0.0186 (3)
C19	0.49348 (13)	0.43229 (15)	1.25172 (10)	0.0203 (3)
H19	0.5441	0.3745	1.2097	0.024*
C20	0.46761 (14)	0.35763 (15)	1.35169 (10)	0.0215 (3)
H20	0.4998	0.2476	1.3760	0.026*
N4	0.39970 (12)	0.43088 (13)	1.41673 (8)	0.0238 (3)
C16	0.35492 (14)	0.58659 (16)	1.37925 (10)	0.0231 (3)
H16	0.3079	0.6415	1.4238	0.028*
C17	0.37312 (13)	0.67179 (16)	1.27954 (10)	0.0207 (3)
H17	0.3377	0.7816	1.2568	0.025*

	U11	U22	U33	U12	U13	U23
N1	0.0246 (6)	0.0248 (6)	0.0228 (6)	−0.0064 (5)	−0.0001 (5)	−0.0092 (5)
N2	0.0197 (5)	0.0236 (6)	0.0209 (6)	−0.0007 (5)	−0.0027 (4)	−0.0095 (5)
N3	0.0199 (5)	0.0226 (6)	0.0238 (6)	−0.0003 (5)	0.0001 (5)	−0.0071 (5)
C28	0.0266 (7)	0.0257 (7)	0.0181 (7)	−0.0088 (6)	0.0001 (5)	−0.0070 (6)
C24	0.0192 (6)	0.0235 (7)	0.0211 (7)	−0.0017 (5)	−0.0004 (5)	−0.0104 (6)
C22	0.0198 (6)	0.0187 (6)	0.0229 (7)	−0.0011 (5)	−0.0013 (5)	−0.0068 (5)
C1	0.0192 (6)	0.0252 (7)	0.0250 (7)	−0.0050 (5)	0.0014 (5)	−0.0119 (6)
C2	0.0174 (6)	0.0218 (7)	0.0243 (7)	−0.0032 (5)	−0.0030 (5)	−0.0102 (6)
C3	0.0191 (6)	0.0176 (6)	0.0215 (7)	−0.0033 (5)	−0.0019 (5)	−0.0090 (5)
C4	0.0173 (6)	0.0208 (6)	0.0254 (7)	−0.0033 (5)	−0.0016 (5)	−0.0108 (6)
C5	0.0205 (6)	0.0209 (6)	0.0234 (7)	−0.0029 (5)	−0.0046 (5)	−0.0070 (6)
C6	0.0165 (6)	0.0191 (6)	0.0225 (7)	−0.0019 (5)	−0.0035 (5)	−0.0094 (6)
C7	0.0199 (6)	0.0213 (7)	0.0197 (7)	−0.0001 (5)	−0.0047 (5)	−0.0078 (5)
C8	0.0182 (6)	0.0194 (7)	0.0212 (7)	−0.0025 (5)	−0.0035 (5)	−0.0094 (6)
C9	0.0180 (6)	0.0250 (7)	0.0225 (7)	−0.0012 (5)	0.0010 (5)	−0.0080 (6)
C10	0.0135 (6)	0.0229 (7)	0.0225 (7)	−0.0037 (5)	−0.0025 (5)	−0.0090 (6)
C11	0.0171 (6)	0.0225 (7)	0.0230 (7)	−0.0028 (5)	−0.0029 (5)	−0.0106 (6)
C12	0.0194 (6)	0.0208 (6)	0.0247 (7)	−0.0041 (5)	−0.0049 (5)	−0.0064 (6)
C13	0.0211 (6)	0.0283 (7)	0.0191 (7)	−0.0085 (6)	−0.0010 (5)	−0.0075 (6)
C14	0.0187 (6)	0.0285 (7)	0.0257 (7)	−0.0066 (5)	0.0013 (5)	−0.0145 (6)
C15	0.0160 (6)	0.0193 (6)	0.0256 (7)	−0.0026 (5)	−0.0017 (5)	−0.0085 (6)
C29	0.0200 (6)	0.0279 (7)	0.0228 (7)	−0.0077 (6)	0.0017 (5)	−0.0128 (6)
C30	0.0167 (6)	0.0221 (7)	0.0206 (7)	−0.0016 (5)	−0.0044 (5)	−0.0089 (5)
C25	0.0182 (6)	0.0188 (6)	0.0213 (7)	−0.0040 (5)	−0.0016 (5)	−0.0096 (5)
C26	0.0166 (6)	0.0211 (6)	0.0242 (7)	−0.0030 (5)	−0.0008 (5)	−0.0093 (6)
C27	0.0224 (7)	0.0215 (7)	0.0239 (7)	−0.0032 (5)	−0.0061 (5)	−0.0059 (6)
C23	0.0143 (6)	0.0211 (7)	0.0211 (7)	−0.0030 (5)	−0.0025 (5)	−0.0092 (6)
N6	0.0197 (5)	0.0231 (6)	0.0197 (6)	−0.0008 (5)	−0.0017 (4)	−0.0090 (5)
C21	0.0154 (6)	0.0209 (7)	0.0214 (7)	−0.0029 (5)	−0.0031 (5)	−0.0094 (6)
N5	0.0195 (5)	0.0203 (6)	0.0214 (6)	−0.0014 (5)	0.0000 (4)	−0.0063 (5)
C18	0.0135 (6)	0.0232 (7)	0.0202 (7)	−0.0038 (5)	−0.0024 (5)	−0.0081 (6)
C19	0.0170 (6)	0.0229 (7)	0.0230 (7)	−0.0031 (5)	−0.0034 (5)	−0.0104 (6)
C20	0.0181 (6)	0.0217 (7)	0.0231 (7)	−0.0030 (5)	−0.0051 (5)	−0.0054 (6)
N4	0.0208 (6)	0.0288 (6)	0.0214 (6)	−0.0051 (5)	−0.0024 (5)	−0.0076 (5)
C16	0.0203 (6)	0.0288 (7)	0.0223 (7)	−0.0043 (6)	−0.0002 (5)	−0.0119 (6)
C17	0.0173 (6)	0.0228 (7)	0.0229 (7)	−0.0026 (5)	−0.0022 (5)	−0.0097 (6)

N1—C1	1.3429 (18)	C11—C12	1.3890 (18)
N1—C5	1.3451 (17)	C11—H11	0.95
N2—C7	1.3338 (17)	C12—C13	1.3904 (18)
N2—C6	1.3445 (17)	C12—H12	0.95
N3—C9	1.3344 (17)	C13—C14	1.3911 (19)
N3—C6	1.3474 (16)	C13—H13	0.95
C28—C29	1.3874 (19)	C14—C15	1.3854 (18)
C28—C27	1.3935 (19)	C14—H14	0.95
C28—H28	0.95	C15—H15	0.95
C24—N6	1.3341 (17)	C29—C30	1.3810 (18)
C24—C23	1.3987 (19)	C29—H29	0.95
C24—H24	0.95	C30—C25	1.4068 (18)
C22—N5	1.3321 (17)	C30—H30	0.95
C22—C23	1.4010 (18)	C25—C26	1.3998 (19)
C22—H22	0.95	C25—C23	1.4746 (18)
C1—C2	1.3861 (18)	C26—C27	1.3853 (18)
C1—H1	0.95	C26—H26	0.95
C2—C3	1.3982 (18)	C27—H27	0.95
C2—H2	0.95	N6—C21	1.3446 (16)
C3—C4	1.3924 (19)	C21—N5	1.3442 (17)
C3—C6	1.4829 (18)	C21—C18	1.4825 (18)
C4—C5	1.3847 (18)	C18—C19	1.3962 (19)
C4—H4	0.95	C18—C17	1.3970 (18)
C5—H5	0.95	C19—C20	1.3808 (18)
C7—C8	1.3998 (18)	C19—H19	0.95
C7—H7	0.95	C20—N4	1.3440 (17)
C8—C9	1.3949 (19)	C20—H20	0.95
C8—C10	1.4757 (18)	N4—C16	1.3458 (18)
C9—H9	0.95	C16—C17	1.3871 (19)
C10—C15	1.4027 (18)	C16—H16	0.95
C10—C11	1.4039 (19)	C17—H17	0.95
C1—N1—C5	116.27 (12)	C12—C13—C14	119.78 (13)
C7—N2—C6	116.84 (11)	C12—C13—H13	120.1
C9—N3—C6	116.34 (11)	C14—C13—H13	120.1
C29—C28—C27	119.71 (12)	C15—C14—C13	120.31 (12)
C29—C28—H28	120.1	C15—C14—H14	119.8
C27—C28—H28	120.1	C13—C14—H14	119.8
N6—C24—C23	123.58 (11)	C14—C15—C10	120.70 (12)
N6—C24—H24	118.2	C14—C15—H15	119.6
C23—C24—H24	118.2	C10—C15—H15	119.6
N5—C22—C23	123.44 (12)	C30—C29—C28	120.36 (12)
N5—C22—H22	118.3	C30—C29—H29	119.8
C23—C22—H22	118.3	C28—C29—H29	119.8
N1—C1—C2	123.93 (12)	C29—C30—C25	120.69 (12)
N1—C1—H1	118	C29—C30—H30	119.7
C2—C1—H1	118	C25—C30—H30	119.7
C1—C2—C3	119.00 (12)	C26—C25—C30	118.38 (12)
C1—C2—H2	120.5	C26—C25—C23	121.73 (11)
C3—C2—H2	120.5	C30—C25—C23	119.88 (11)
C4—C3—C2	117.68 (12)	C27—C26—C25	120.69 (12)
C4—C3—C6	121.26 (11)	C27—C26—H26	119.7
C2—C3—C6	121.03 (12)	C25—C26—H26	119.7
C5—C4—C3	118.96 (12)	C26—C27—C28	120.18 (12)
C5—C4—H4	120.5	C26—C27—H27	119.9
C3—C4—H4	120.5	C28—C27—H27	119.9
N1—C5—C4	124.14 (12)	C24—C23—C22	114.48 (12)
N1—C5—H5	117.9	C24—C23—C25	122.19 (11)
C4—C5—H5	117.9	C22—C23—C25	123.33 (12)
N2—C6—N3	125.23 (12)	C24—N6—C21	116.46 (11)
N2—C6—C3	117.34 (11)	N5—C21—N6	125.40 (12)
N3—C6—C3	117.42 (11)	N5—C21—C18	118.22 (11)
N2—C7—C8	123.18 (12)	N6—C21—C18	116.37 (11)
N2—C7—H7	118.4	C22—N5—C21	116.63 (11)
C8—C7—H7	118.4	C19—C18—C17	117.45 (12)
C9—C8—C7	114.70 (12)	C19—C18—C21	120.29 (11)
C9—C8—C10	123.20 (11)	C17—C18—C21	122.26 (12)
C7—C8—C10	122.08 (12)	C20—C19—C18	119.28 (12)
N3—C9—C8	123.71 (11)	C20—C19—H19	120.4
N3—C9—H9	118.1	C18—C19—H19	120.4
C8—C9—H9	118.1	N4—C20—C19	124.09 (12)
C15—C10—C11	118.38 (12)	N4—C20—H20	118
C15—C10—C8	120.59 (12)	C19—C20—H20	118
C11—C10—C8	120.99 (11)	C20—N4—C16	116.18 (12)
C12—C11—C10	120.74 (12)	N4—C16—C17	124.03 (12)
C12—C11—H11	119.6	N4—C16—H16	118
C10—C11—H11	119.6	C17—C16—H16	118
C11—C12—C13	120.08 (12)	C16—C17—C18	118.96 (12)
C11—C12—H12	120	C16—C17—H17	120.5
C13—C12—H12	120	C18—C17—H17	120.5
C5—N1—C1—C2	−0.23 (18)	C27—C28—C29—C30	−0.06 (19)
N1—C1—C2—C3	1.52 (19)	C28—C29—C30—C25	−0.50 (18)
C1—C2—C3—C4	−1.28 (18)	C29—C30—C25—C26	0.86 (18)
C1—C2—C3—C6	−179.38 (11)	C29—C30—C25—C23	−179.99 (11)
C2—C3—C4—C5	−0.09 (18)	C30—C25—C26—C27	−0.67 (18)
C6—C3—C4—C5	178.00 (11)	C23—C25—C26—C27	−179.80 (11)
C1—N1—C5—C4	−1.28 (19)	C25—C26—C27—C28	0.13 (18)
C3—C4—C5—N1	1.46 (19)	C29—C28—C27—C26	0.25 (19)
C7—N2—C6—N3	−0.15 (18)	N6—C24—C23—C22	−0.22 (18)
C7—N2—C6—C3	178.6 (1)	N6—C24—C23—C25	179.12 (11)
C9—N3—C6—N2	−0.02 (19)	N5—C22—C23—C24	0.14 (18)
C9—N3—C6—C3	−178.77 (11)	N5—C22—C23—C25	−179.20 (11)
C4—C3—C6—N2	−158.60 (12)	C26—C25—C23—C24	148.58 (13)
C2—C3—C6—N2	19.42 (17)	C30—C25—C23—C24	−30.54 (17)
C4—C3—C6—N3	20.25 (17)	C26—C25—C23—C22	−32.13 (18)
C2—C3—C6—N3	−161.73 (12)	C30—C25—C23—C22	148.75 (13)
C6—N2—C7—C8	0.11 (18)	C23—C24—N6—C21	0.22 (18)
N2—C7—C8—C9	0.08 (18)	C24—N6—C21—N5	−0.14 (18)
N2—C7—C8—C10	178.41 (11)	C24—N6—C21—C18	179.6 (1)
C6—N3—C9—C8	0.23 (19)	C23—C22—N5—C21	−0.07 (18)
C7—C8—C9—N3	−0.26 (19)	N6—C21—N5—C22	0.07 (19)
C10—C8—C9—N3	−178.57 (11)	C18—C21—N5—C22	−179.67 (11)
C9—C8—C10—C15	33.47 (18)	N5—C21—C18—C19	160.88 (12)
C7—C8—C10—C15	−144.72 (13)	N6—C21—C18—C19	−18.89 (17)
C9—C8—C10—C11	−148.99 (13)	N5—C21—C18—C17	−19.43 (18)
C7—C8—C10—C11	32.82 (18)	N6—C21—C18—C17	160.81 (12)
C15—C10—C11—C12	0.05 (18)	C17—C18—C19—C20	1.14 (18)
C8—C10—C11—C12	−177.54 (11)	C21—C18—C19—C20	−179.15 (10)
C10—C11—C12—C13	0.43 (18)	C18—C19—C20—N4	−1.45 (19)
C11—C12—C13—C14	−0.57 (19)	C19—C20—N4—C16	0.40 (18)
C12—C13—C14—C15	0.24 (19)	C20—N4—C16—C17	0.95 (19)
C13—C14—C15—C10	0.25 (18)	N4—C16—C17—C18	−1.19 (19)
C11—C10—C15—C14	−0.39 (18)	C19—C18—C17—C16	0.08 (18)
C8—C10—C15—C14	177.20 (11)	C21—C18—C17—C16	−179.62 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N5i	0.95	2.55	3.3818 (18)	147
C9—H9···N6ii	0.95	2.56	3.4027 (18)	148
C22—H22···N2i	0.95	2.54	3.3784 (18)	147
C24—H24···N3ii	0.95	2.56	3.4049 (19)	149
C1—H1···Cg3iii	0.95	2.91	3.5925 (15)	129.
C4—H4···Cg3	0.95	2.72	3.4163 (15)	130.
C12—H12···Cg1i	0.95	2.89	3.5844 (15)	131.
C15—H15···Cg1iv	0.95	2.92	3.5202 (15)	122.
C17—H17···Cg6v	0.95	2.84	3.5561 (16)	133.
C20—H20···Cg6ii	0.95	2.85	3.5251 (15)	129.
C26—H26···Cg5	0.95	2.86	3.5242 (15)	128.
C29—H29···Cg5vi	0.95	2.77	3.4451 (15)	129.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯N5i	0.95	2.55	3.3818 (18)	147
C9—H9⋯N6ii	0.95	2.56	3.4027 (18)	148
C22—H22⋯N2i	0.95	2.54	3.3784 (18)	147
C24—H24⋯N3ii	0.95	2.56	3.4049 (19)	149
C1—H1⋯Cg3iii	0.95	2.91	3.5925 (15)	129
C4—H4⋯Cg3	0.95	2.72	3.4163 (15)	130
C12—H12⋯Cg1i	0.95	2.89	3.5844 (15)	131
C15—H15⋯Cg1iv	0.95	2.92	3.5202 (15)	122
C17—H17⋯Cg6v	0.95	2.84	3.5561 (16)	133
C20—H20⋯Cg6ii	0.95	2.85	3.5251 (15)	129
C26—H26⋯Cg5	0.95	2.86	3.5242 (15)	128
C29—H29⋯Cg5vi	0.95	2.77	3.4451 (15)	129

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . Cg1 is the centroid of the N1/C1-C5 ring, Cg3 is the centroid of the N4/C16–C20 ring, Cg5 is the centroid of the C10–C15 ring and Cg6 is the centroid of the C25–C30 ring.