2,4,6-Tris(2,4-dimethyl-phen-yl)-1,3,5-triazine.

Two virtually superimposable mol-ecules comprise the asymmetric unit of the title compound, C(27)H(27)N(3). The range of dihedral angles between the central 1,3,5-triazine ring and the attached benzene rings is 20.88 (14)-31.36 (14)°, and the shape of each mol-ecule is of a flattened bowl. The crystal packing features weak C-H⋯π bonds and π-π inter-actions between triazine and benzene rings [centroid-centroid separations = 3.7696 (17) and 3.7800 (18) Å] that result in the formation of supra-molecular layers in the ac plane. The crystal studied was a non-merohedral twin with a minor twin component of 20.7 (3)%.

Related literature

For the synthesis, see: Orban et al. (1988 ▶). For the crystal structure of s-triphenyl­triazine, see: Damiani et al. (1965 ▶). For homologues, see: Bosch & Barnes (2002 ▶); Thalladi et al. (1999 ▶); Volkis et al. (2003 ▶). For the separation of twinned diffraction indices, see: Spek (2009 ▶).

Experimental

Crystal data

C27H27N3

M = 393.52

Triclinic,

a = 7.4663 (4) Å

b = 15.0789 (13) Å

c = 19.7266 (12) Å

α = 109.016 (7)°

β = 90.949 (5)°

γ = 93.717 (6)°

V = 2093.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 100 K

0.30 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.978, T max = 0.996

14777 measured reflections

9605 independent reflections

5518 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.085

wR(F 2) = 0.222

S = 1.04

9597 reflections

554 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶), Qmol (Gans & Shalloway, 2001 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016261/hb6737sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016261/hb6737Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016261/hb6737Isup3.cml

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

C27H27N3	Z = 4
Mr = 393.52	F(000) = 840
Triclinic, P1	Dx = 1.248 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4663 (4) Å	Cell parameters from 2806 reflections
b = 15.0789 (13) Å	θ = 2.7–27.5°
c = 19.7266 (12) Å	µ = 0.07 mm−1
α = 109.016 (7)°	T = 100 K
β = 90.949 (5)°	Plate, colourless
γ = 93.717 (6)°	0.30 × 0.15 × 0.05 mm
V = 2093.6 (2) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	9605 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5518 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.058
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.7°
ω scan	h = −9→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −16→19
Tmin = 0.978, Tmax = 0.996	l = −25→25
14777 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)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.222	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0673P)2 + 1.4043P] where P = (Fo2 + 2Fc2)/3
9597 reflections	(Δ/σ)max = 0.001
554 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

	x	y	z	Uiso*/Ueq
N1	0.2281 (4)	0.3830 (2)	0.89667 (14)	0.0177 (6)
N2	0.2497 (4)	0.2425 (2)	0.92575 (14)	0.0178 (6)
N3	0.2594 (4)	0.3902 (2)	1.01875 (14)	0.0169 (6)
N4	0.2354 (3)	0.6128 (2)	0.57186 (14)	0.0164 (6)
N5	0.2624 (4)	0.6141 (2)	0.45247 (14)	0.0171 (6)
N6	0.2400 (4)	0.7575 (2)	0.54849 (14)	0.0183 (6)
C1	0.2352 (4)	0.2892 (2)	0.87866 (17)	0.0164 (7)
C2	0.2602 (4)	0.2959 (2)	0.99515 (17)	0.0169 (7)
C3	0.2415 (4)	0.4304 (2)	0.96749 (17)	0.0160 (7)
C4	0.2182 (4)	0.2313 (2)	0.80171 (18)	0.0180 (7)
C5	0.2769 (4)	0.2636 (2)	0.74558 (18)	0.0197 (7)
C6	0.2461 (4)	0.2028 (3)	0.67513 (18)	0.0205 (8)
H6	0.2847	0.2238	0.6369	0.025*
C7	0.1615 (5)	0.1129 (3)	0.65849 (18)	0.0213 (8)
C8	0.1094 (4)	0.0810 (2)	0.71473 (18)	0.0199 (7)
H8	0.0544	0.0193	0.7048	0.024*
C9	0.1381 (4)	0.1396 (2)	0.78498 (18)	0.0195 (7)
H9	0.1026	0.1171	0.8228	0.023*
C10	0.3764 (5)	0.3579 (3)	0.75557 (18)	0.0235 (8)
H10A	0.4585	0.3746	0.7978	0.035*
H10B	0.2899	0.4060	0.7624	0.035*
H10C	0.4451	0.3543	0.7130	0.035*
C11	0.1230 (5)	0.0521 (3)	0.58162 (18)	0.0277 (9)
H11A	0.2109	0.0696	0.5510	0.042*
H11B	0.0018	0.0612	0.5664	0.042*
H11C	0.1310	−0.0141	0.5774	0.042*
C12	0.2612 (4)	0.2466 (2)	1.04930 (17)	0.0172 (7)
C13	0.1863 (5)	0.1538 (2)	1.02738 (18)	0.0203 (8)
H13	0.1509	0.1234	0.9783	0.024*
C14	0.1624 (5)	0.1049 (3)	1.07584 (18)	0.0219 (8)
H14	0.1100	0.0421	1.0597	0.026*
C15	0.2147 (4)	0.1475 (2)	1.14763 (18)	0.0185 (7)
C16	0.2977 (4)	0.2383 (2)	1.16825 (18)	0.0202 (8)
H16	0.3387	0.2668	1.2169	0.024*
C17	0.3236 (4)	0.2895 (2)	1.12107 (17)	0.0181 (7)
C18	0.1833 (5)	0.0972 (3)	1.20146 (19)	0.0264 (8)
H18A	0.1205	0.0354	1.1776	0.040*
H18B	0.1101	0.1344	1.2397	0.040*
H18C	0.2989	0.0892	1.2221	0.040*
C19	0.4222 (5)	0.3859 (2)	1.15022 (18)	0.0229 (8)
H19A	0.4935	0.3903	1.1935	0.034*
H19B	0.3350	0.4340	1.1621	0.034*
H19C	0.5018	0.3958	1.1139	0.034*
C20	0.2397 (4)	0.5344 (2)	0.99277 (17)	0.0159 (7)
C21	0.3143 (4)	0.5832 (2)	1.06164 (17)	0.0177 (7)
H21	0.3577	0.5484	1.0901	0.021*
C22	0.3266 (4)	0.6807 (2)	1.08958 (18)	0.0193 (7)
H22	0.3776	0.7118	1.1365	0.023*
C23	0.2634 (4)	0.7331 (2)	1.04829 (18)	0.0185 (7)
C24	0.1862 (4)	0.6847 (2)	0.98088 (18)	0.0200 (7)
H24	0.1413	0.7200	0.9532	0.024*
C25	0.1710 (4)	0.5862 (2)	0.95141 (17)	0.0184 (7)
C26	0.2836 (5)	0.8396 (3)	1.0768 (2)	0.0288 (9)
H26A	0.2511	0.8645	1.0385	0.043*
H26B	0.4085	0.8606	1.0933	0.043*
H26C	0.2043	0.8625	1.1169	0.043*
C27	0.0759 (5)	0.5441 (3)	0.87846 (18)	0.0223 (8)
H27A	0.0037	0.5910	0.8688	0.033*
H27B	−0.0025	0.4891	0.8777	0.033*
H27C	0.1650	0.5249	0.8415	0.033*
C28	0.2320 (4)	0.7064 (2)	0.59323 (17)	0.0171 (7)
C29	0.2525 (4)	0.5694 (2)	0.50159 (17)	0.0156 (7)
C30	0.2538 (4)	0.7078 (2)	0.47921 (17)	0.0160 (7)
C31	0.2327 (4)	0.7581 (2)	0.67135 (17)	0.0170 (7)
C32	0.1785 (4)	0.7160 (2)	0.72288 (18)	0.0188 (7)
C33	0.2087 (4)	0.7689 (3)	0.79568 (18)	0.0209 (8)
H33	0.1746	0.7408	0.8307	0.025*
C34	0.2864 (4)	0.8609 (3)	0.81899 (18)	0.0202 (8)
C35	0.3299 (5)	0.9030 (2)	0.76749 (18)	0.0212 (8)
H35	0.3784	0.9665	0.7819	0.025*
C36	0.3023 (4)	0.8519 (2)	0.69500 (18)	0.0204 (8)
H36	0.3316	0.8816	0.6605	0.024*
C37	0.0851 (5)	0.6187 (2)	0.70535 (18)	0.0230 (8)
H37A	0.0180	0.6147	0.7467	0.034*
H37B	0.1748	0.5719	0.6942	0.034*
H37C	0.0021	0.6064	0.6638	0.034*
C38	0.3233 (5)	0.9130 (3)	0.89758 (18)	0.0273 (9)
H38A	0.2176	0.9048	0.9243	0.041*
H38B	0.3500	0.9800	0.9049	0.041*
H38C	0.4264	0.8881	0.9147	0.041*
C39	0.2682 (4)	0.7613 (2)	0.42778 (17)	0.0155 (7)
C40	0.3514 (4)	0.8527 (2)	0.45439 (18)	0.0184 (7)
H40	0.3859	0.8784	0.5039	0.022*
C41	0.3844 (4)	0.9064 (2)	0.40997 (18)	0.0193 (7)
H41	0.4430	0.9677	0.4290	0.023*
C42	0.3317 (4)	0.8704 (2)	0.33773 (18)	0.0191 (7)
C43	0.2414 (4)	0.7819 (2)	0.31238 (18)	0.0195 (7)
H43	0.1998	0.7584	0.2636	0.023*
C44	0.2091 (4)	0.7257 (2)	0.35570 (18)	0.0175 (7)
C45	0.3768 (5)	0.9246 (2)	0.28692 (19)	0.0218 (8)
H45A	0.2726	0.9197	0.2547	0.033*
H45B	0.4789	0.8982	0.2586	0.033*
H45C	0.4079	0.9908	0.3146	0.033*
C46	0.1078 (5)	0.6305 (2)	0.32061 (18)	0.0242 (8)
H46A	0.0205	0.6185	0.3537	0.036*
H46B	0.1929	0.5813	0.3089	0.036*
H46C	0.0447	0.6302	0.2766	0.036*
C47	0.2593 (4)	0.4660 (2)	0.47766 (17)	0.0167 (7)
C48	0.3293 (4)	0.4124 (3)	0.41262 (18)	0.0198 (8)
C49	0.3207 (4)	0.3143 (3)	0.39598 (18)	0.0203 (8)
H49	0.3674	0.2778	0.3519	0.024*
C50	0.2477 (4)	0.2679 (2)	0.44048 (19)	0.0200 (7)
C51	0.1841 (4)	0.3229 (2)	0.50602 (18)	0.0203 (8)
H51	0.1363	0.2935	0.5383	0.024*
C52	0.1902 (4)	0.4195 (2)	0.52416 (17)	0.0173 (7)
H52	0.1469	0.4555	0.5690	0.021*
C53	0.4187 (5)	0.4523 (3)	0.35912 (18)	0.0219 (8)
H53A	0.4951	0.4061	0.3287	0.033*
H53B	0.4924	0.5101	0.3850	0.033*
H53C	0.3264	0.4666	0.3291	0.033*
C54	0.2342 (5)	0.1619 (2)	0.4188 (2)	0.0269 (8)
H54A	0.2463	0.1431	0.4616	0.040*
H54B	0.3303	0.1369	0.3863	0.040*
H54C	0.1174	0.1369	0.3944	0.040*

	U11	U22	U33	U12	U13	U23
N1	0.0190 (15)	0.0186 (16)	0.0168 (15)	0.0022 (11)	0.0005 (11)	0.0072 (12)
N2	0.0189 (15)	0.0212 (16)	0.0149 (15)	−0.0009 (11)	−0.0018 (11)	0.0088 (13)
N3	0.0200 (15)	0.0170 (15)	0.0151 (15)	−0.0002 (11)	0.0005 (11)	0.0075 (12)
N4	0.0181 (15)	0.0171 (15)	0.0148 (15)	0.0004 (11)	0.0002 (11)	0.0065 (12)
N5	0.0203 (15)	0.0178 (15)	0.0159 (15)	0.0018 (11)	0.0017 (11)	0.0091 (12)
N6	0.0215 (15)	0.0194 (16)	0.0151 (15)	−0.0016 (12)	0.0004 (11)	0.0078 (12)
C1	0.0154 (17)	0.0183 (18)	0.0160 (17)	0.0022 (13)	0.0027 (12)	0.0061 (14)
C2	0.0159 (17)	0.0190 (18)	0.0158 (17)	0.0002 (13)	0.0007 (12)	0.0059 (14)
C3	0.0151 (17)	0.0221 (19)	0.0129 (17)	0.0009 (13)	0.0002 (12)	0.0088 (14)
C4	0.0179 (17)	0.0206 (19)	0.0168 (17)	0.0042 (13)	0.0003 (12)	0.0073 (15)
C5	0.0195 (18)	0.0221 (19)	0.0200 (18)	0.0018 (14)	−0.0001 (13)	0.0101 (15)
C6	0.0195 (18)	0.028 (2)	0.0162 (18)	0.0071 (14)	0.0010 (13)	0.0100 (16)
C7	0.0214 (19)	0.027 (2)	0.0150 (18)	0.0065 (14)	0.0000 (13)	0.0048 (15)
C8	0.0174 (18)	0.0193 (19)	0.0227 (19)	0.0026 (13)	−0.0002 (13)	0.0062 (15)
C9	0.0203 (18)	0.0215 (19)	0.0196 (18)	0.0010 (14)	0.0008 (13)	0.0108 (15)
C10	0.028 (2)	0.027 (2)	0.0194 (19)	0.0045 (15)	0.0058 (14)	0.0115 (16)
C11	0.025 (2)	0.033 (2)	0.022 (2)	−0.0002 (16)	−0.0011 (14)	0.0046 (17)
C12	0.0183 (17)	0.0188 (18)	0.0178 (18)	0.0052 (13)	0.0022 (12)	0.0098 (15)
C13	0.0250 (19)	0.0174 (19)	0.0178 (18)	−0.0001 (14)	0.0005 (14)	0.0050 (15)
C14	0.027 (2)	0.0180 (19)	0.024 (2)	0.0019 (14)	0.0023 (14)	0.0117 (16)
C15	0.0186 (18)	0.0202 (19)	0.0214 (19)	0.0046 (13)	0.0037 (13)	0.0124 (15)
C16	0.0230 (19)	0.022 (2)	0.0161 (18)	0.0034 (14)	−0.0002 (13)	0.0071 (15)
C17	0.0179 (17)	0.0230 (19)	0.0156 (17)	0.0019 (13)	0.0019 (12)	0.0093 (15)
C18	0.031 (2)	0.029 (2)	0.025 (2)	0.0021 (16)	0.0009 (15)	0.0173 (17)
C19	0.029 (2)	0.026 (2)	0.0151 (18)	−0.0032 (15)	−0.0022 (14)	0.0086 (16)
C20	0.0164 (17)	0.0178 (18)	0.0158 (17)	0.0020 (13)	0.0018 (12)	0.0085 (14)
C21	0.0177 (17)	0.0222 (19)	0.0159 (17)	−0.0002 (13)	−0.0010 (12)	0.0104 (15)
C22	0.0220 (18)	0.0214 (19)	0.0141 (17)	0.0015 (14)	0.0001 (13)	0.0053 (15)
C23	0.0172 (17)	0.0188 (18)	0.0214 (19)	0.0019 (13)	0.0044 (13)	0.0090 (15)
C24	0.0242 (19)	0.022 (2)	0.0166 (18)	0.0059 (14)	0.0041 (13)	0.0098 (15)
C25	0.0191 (18)	0.0208 (19)	0.0175 (18)	0.0030 (13)	0.0026 (13)	0.0088 (15)
C26	0.041 (2)	0.020 (2)	0.026 (2)	0.0015 (16)	0.0005 (16)	0.0093 (17)
C27	0.0255 (19)	0.025 (2)	0.0186 (18)	0.0052 (15)	0.0018 (14)	0.0091 (16)
C28	0.0168 (17)	0.0217 (19)	0.0164 (17)	−0.0005 (13)	0.0011 (12)	0.0114 (15)
C29	0.0163 (17)	0.0191 (18)	0.0134 (17)	−0.0006 (13)	−0.0007 (12)	0.0087 (14)
C30	0.0173 (17)	0.0181 (18)	0.0140 (17)	−0.0005 (13)	0.0007 (12)	0.0076 (14)
C31	0.0192 (17)	0.0186 (18)	0.0145 (17)	0.0020 (13)	−0.0002 (12)	0.0074 (14)
C32	0.0185 (18)	0.0213 (19)	0.0194 (18)	0.0014 (14)	−0.0018 (13)	0.0107 (15)
C33	0.0227 (19)	0.025 (2)	0.0186 (18)	0.0003 (14)	0.0018 (13)	0.0119 (16)
C34	0.0203 (18)	0.024 (2)	0.0162 (18)	0.0029 (14)	0.0016 (13)	0.0062 (15)
C35	0.0260 (19)	0.0165 (18)	0.0218 (19)	0.0002 (14)	0.0017 (14)	0.0077 (15)
C36	0.0244 (19)	0.023 (2)	0.0164 (18)	0.0019 (14)	0.0041 (13)	0.0095 (15)
C37	0.0251 (19)	0.023 (2)	0.0220 (19)	−0.0058 (15)	0.0020 (14)	0.0099 (16)
C38	0.032 (2)	0.031 (2)	0.0171 (19)	0.0004 (16)	0.0031 (15)	0.0059 (17)
C39	0.0180 (17)	0.0158 (17)	0.0152 (17)	0.0017 (13)	0.0035 (12)	0.0082 (14)
C40	0.0199 (18)	0.0210 (19)	0.0159 (17)	0.0017 (14)	0.0016 (13)	0.0081 (15)
C41	0.0218 (18)	0.0171 (18)	0.0205 (18)	−0.0005 (13)	0.0020 (13)	0.0087 (15)
C42	0.0193 (18)	0.0208 (19)	0.0223 (19)	0.0045 (13)	0.0060 (13)	0.0131 (16)
C43	0.0181 (17)	0.027 (2)	0.0188 (18)	0.0031 (14)	0.0032 (13)	0.0139 (16)
C44	0.0180 (17)	0.0181 (18)	0.0185 (18)	−0.0002 (13)	0.0035 (13)	0.0087 (15)
C45	0.0266 (19)	0.0191 (19)	0.025 (2)	0.0012 (14)	0.0038 (14)	0.0139 (16)
C46	0.029 (2)	0.023 (2)	0.0215 (19)	−0.0018 (15)	−0.0043 (14)	0.0097 (16)
C47	0.0156 (17)	0.0231 (19)	0.0147 (17)	0.0012 (13)	0.0005 (12)	0.0108 (15)
C48	0.0187 (18)	0.0224 (19)	0.0206 (19)	−0.0007 (14)	−0.0021 (13)	0.0105 (15)
C49	0.0213 (18)	0.0219 (19)	0.0188 (18)	0.0044 (14)	0.0003 (13)	0.0076 (15)
C50	0.0208 (18)	0.0185 (18)	0.0229 (19)	−0.0013 (14)	−0.0022 (13)	0.0103 (16)
C51	0.0234 (19)	0.0200 (19)	0.0227 (19)	0.0000 (14)	0.0022 (14)	0.0144 (16)
C52	0.0187 (18)	0.0202 (18)	0.0150 (17)	0.0001 (13)	0.0007 (13)	0.0086 (15)
C53	0.0214 (19)	0.026 (2)	0.0218 (19)	0.0024 (14)	0.0015 (14)	0.0117 (16)
C54	0.038 (2)	0.018 (2)	0.026 (2)	0.0004 (16)	0.0031 (16)	0.0110 (17)

N1—C3	1.345 (4)	C26—H26A	0.9800
N1—C1	1.346 (4)	C26—H26B	0.9800
N2—C2	1.341 (4)	C26—H26C	0.9800
N2—C1	1.343 (4)	C27—H27A	0.9800
N3—C2	1.344 (4)	C27—H27B	0.9800
N3—C3	1.347 (4)	C27—H27C	0.9800
N4—C28	1.338 (4)	C28—C31	1.483 (5)
N4—C29	1.338 (4)	C29—C47	1.478 (5)
N5—C30	1.344 (4)	C30—C39	1.489 (4)
N5—C29	1.350 (4)	C31—C36	1.398 (5)
N6—C30	1.337 (4)	C31—C32	1.415 (4)
N6—C28	1.347 (4)	C32—C33	1.403 (5)
C1—C4	1.483 (5)	C32—C37	1.512 (4)
C2—C12	1.487 (5)	C33—C34	1.394 (5)
C3—C20	1.484 (5)	C33—H33	0.9500
C4—C9	1.403 (5)	C34—C35	1.395 (5)
C4—C5	1.412 (5)	C34—C38	1.504 (5)
C5—C6	1.399 (5)	C35—C36	1.390 (5)
C5—C10	1.513 (5)	C35—H35	0.9500
C6—C7	1.391 (5)	C36—H36	0.9500
C6—H6	0.9500	C37—H37A	0.9800
C7—C8	1.397 (5)	C37—H37B	0.9800
C7—C11	1.506 (5)	C37—H37C	0.9800
C8—C9	1.383 (5)	C38—H38A	0.9800
C8—H8	0.9500	C38—H38B	0.9800
C9—H9	0.9500	C38—H38C	0.9800
C10—H10A	0.9800	C39—C44	1.399 (4)
C10—H10B	0.9800	C39—C40	1.403 (4)
C10—H10C	0.9800	C40—C41	1.388 (5)
C11—H11A	0.9800	C40—H40	0.9500
C11—H11B	0.9800	C41—C42	1.389 (5)
C11—H11C	0.9800	C41—H41	0.9500
C12—C13	1.398 (4)	C42—C43	1.388 (5)
C12—C17	1.408 (4)	C42—C45	1.514 (4)
C13—C14	1.392 (5)	C43—C44	1.399 (4)
C13—H13	0.9500	C43—H43	0.9500
C14—C15	1.388 (5)	C44—C46	1.519 (4)
C14—H14	0.9500	C45—H45A	0.9800
C15—C16	1.393 (5)	C45—H45B	0.9800
C15—C18	1.506 (5)	C45—H45C	0.9800
C16—C17	1.398 (5)	C46—H46A	0.9800
C16—H16	0.9500	C46—H46B	0.9800
C17—C19	1.513 (5)	C46—H46C	0.9800
C18—H18A	0.9800	C47—C48	1.405 (5)
C18—H18B	0.9800	C47—C52	1.409 (4)
C18—H18C	0.9800	C48—C49	1.403 (5)
C19—H19A	0.9800	C48—C53	1.519 (5)
C19—H19B	0.9800	C49—C50	1.387 (5)
C19—H19C	0.9800	C49—H49	0.9500
C20—C21	1.402 (4)	C50—C51	1.399 (5)
C20—C25	1.411 (5)	C50—C54	1.510 (5)
C21—C22	1.389 (5)	C51—C52	1.379 (5)
C21—H21	0.9500	C51—H51	0.9500
C22—C23	1.401 (5)	C52—H52	0.9500
C22—H22	0.9500	C53—H53A	0.9800
C23—C24	1.386 (5)	C53—H53B	0.9800
C23—C26	1.515 (5)	C53—H53C	0.9800
C24—C25	1.404 (5)	C54—H54A	0.9800
C24—H24	0.9500	C54—H54B	0.9800
C25—C27	1.514 (4)	C54—H54C	0.9800
C3—N1—C1	115.2 (3)	C25—C27—H27C	109.5
C2—N2—C1	115.5 (3)	H27A—C27—H27C	109.5
C2—N3—C3	115.6 (3)	H27B—C27—H27C	109.5
C28—N4—C29	116.5 (3)	N4—C28—N6	124.0 (3)
C30—N5—C29	114.8 (3)	N4—C28—C31	118.2 (3)
C30—N6—C28	115.1 (3)	N6—C28—C31	117.6 (3)
N2—C1—N1	124.8 (3)	N4—C29—N5	124.0 (3)
N2—C1—C4	116.5 (3)	N4—C29—C47	116.9 (3)
N1—C1—C4	118.7 (3)	N5—C29—C47	119.1 (3)
N2—C2—N3	124.4 (3)	N6—C30—N5	125.5 (3)
N2—C2—C12	117.3 (3)	N6—C30—C39	117.2 (3)
N3—C2—C12	118.1 (3)	N5—C30—C39	117.3 (3)
N1—C3—N3	124.5 (3)	C36—C31—C32	118.8 (3)
N1—C3—C20	119.3 (3)	C36—C31—C28	117.5 (3)
N3—C3—C20	116.2 (3)	C32—C31—C28	123.6 (3)
C9—C4—C5	119.2 (3)	C33—C32—C31	117.9 (3)
C9—C4—C1	117.0 (3)	C33—C32—C37	117.3 (3)
C5—C4—C1	123.7 (3)	C31—C32—C37	124.7 (3)
C6—C5—C4	117.8 (3)	C34—C33—C32	123.0 (3)
C6—C5—C10	117.1 (3)	C34—C33—H33	118.5
C4—C5—C10	125.1 (3)	C32—C33—H33	118.5
C7—C6—C5	123.0 (3)	C33—C34—C35	118.2 (3)
C7—C6—H6	118.5	C33—C34—C38	120.8 (3)
C5—C6—H6	118.5	C35—C34—C38	121.0 (3)
C6—C7—C8	118.5 (3)	C36—C35—C34	119.9 (3)
C6—C7—C11	120.8 (3)	C36—C35—H35	120.0
C8—C7—C11	120.7 (3)	C34—C35—H35	120.0
C9—C8—C7	119.9 (3)	C35—C36—C31	122.0 (3)
C9—C8—H8	120.1	C35—C36—H36	119.0
C7—C8—H8	120.1	C31—C36—H36	119.0
C8—C9—C4	121.6 (3)	C32—C37—H37A	109.5
C8—C9—H9	119.2	C32—C37—H37B	109.5
C4—C9—H9	119.2	H37A—C37—H37B	109.5
C5—C10—H10A	109.5	C32—C37—H37C	109.5
C5—C10—H10B	109.5	H37A—C37—H37C	109.5
H10A—C10—H10B	109.5	H37B—C37—H37C	109.5
C5—C10—H10C	109.5	C34—C38—H38A	109.5
H10A—C10—H10C	109.5	C34—C38—H38B	109.5
H10B—C10—H10C	109.5	H38A—C38—H38B	109.5
C7—C11—H11A	109.5	C34—C38—H38C	109.5
C7—C11—H11B	109.5	H38A—C38—H38C	109.5
H11A—C11—H11B	109.5	H38B—C38—H38C	109.5
C7—C11—H11C	109.5	C44—C39—C40	118.9 (3)
H11A—C11—H11C	109.5	C44—C39—C30	124.6 (3)
H11B—C11—H11C	109.5	C40—C39—C30	116.5 (3)
C13—C12—C17	119.1 (3)	C41—C40—C39	121.5 (3)
C13—C12—C2	116.9 (3)	C41—C40—H40	119.3
C17—C12—C2	123.9 (3)	C39—C40—H40	119.3
C14—C13—C12	121.4 (3)	C40—C41—C42	120.0 (3)
C14—C13—H13	119.3	C40—C41—H41	120.0
C12—C13—H13	119.3	C42—C41—H41	120.0
C15—C14—C13	120.3 (3)	C43—C42—C41	118.4 (3)
C15—C14—H14	119.9	C43—C42—C45	120.4 (3)
C13—C14—H14	119.8	C41—C42—C45	121.2 (3)
C14—C15—C16	117.8 (3)	C42—C43—C44	122.7 (3)
C14—C15—C18	121.1 (3)	C42—C43—H43	118.6
C16—C15—C18	121.1 (3)	C44—C43—H43	118.6
C15—C16—C17	123.4 (3)	C39—C44—C43	118.4 (3)
C15—C16—H16	118.3	C39—C44—C46	124.8 (3)
C17—C16—H16	118.3	C43—C44—C46	116.8 (3)
C16—C17—C12	117.8 (3)	C42—C45—H45A	109.5
C16—C17—C19	117.6 (3)	C42—C45—H45B	109.5
C12—C17—C19	124.6 (3)	H45A—C45—H45B	109.5
C15—C18—H18A	109.5	C42—C45—H45C	109.5
C15—C18—H18B	109.5	H45A—C45—H45C	109.5
H18A—C18—H18B	109.5	H45B—C45—H45C	109.5
C15—C18—H18C	109.5	C44—C46—H46A	109.5
H18A—C18—H18C	109.5	C44—C46—H46B	109.5
H18B—C18—H18C	109.5	H46A—C46—H46B	109.5
C17—C19—H19A	109.5	C44—C46—H46C	109.5
C17—C19—H19B	109.5	H46A—C46—H46C	109.5
H19A—C19—H19B	109.5	H46B—C46—H46C	109.5
C17—C19—H19C	109.5	C48—C47—C52	118.8 (3)
H19A—C19—H19C	109.5	C48—C47—C29	124.5 (3)
H19B—C19—H19C	109.5	C52—C47—C29	116.7 (3)
C21—C20—C25	118.8 (3)	C49—C48—C47	118.0 (3)
C21—C20—C3	117.1 (3)	C49—C48—C53	116.8 (3)
C25—C20—C3	124.0 (3)	C47—C48—C53	125.1 (3)
C22—C21—C20	122.1 (3)	C50—C49—C48	123.4 (3)
C22—C21—H21	119.0	C50—C49—H49	118.3
C20—C21—H21	119.0	C48—C49—H49	118.3
C21—C22—C23	119.7 (3)	C49—C50—C51	117.6 (3)
C21—C22—H22	120.2	C49—C50—C54	121.5 (3)
C23—C22—H22	120.2	C51—C50—C54	121.0 (3)
C24—C23—C22	118.2 (3)	C52—C51—C50	120.6 (3)
C24—C23—C26	121.6 (3)	C52—C51—H51	119.7
C22—C23—C26	120.2 (3)	C50—C51—H51	119.7
C23—C24—C25	123.4 (3)	C51—C52—C47	121.5 (3)
C23—C24—H24	118.3	C51—C52—H52	119.2
C25—C24—H24	118.3	C47—C52—H52	119.2
C24—C25—C20	117.8 (3)	C48—C53—H53A	109.5
C24—C25—C27	116.9 (3)	C48—C53—H53B	109.5
C20—C25—C27	125.3 (3)	H53A—C53—H53B	109.5
C23—C26—H26A	109.5	C48—C53—H53C	109.5
C23—C26—H26B	109.5	H53A—C53—H53C	109.5
H26A—C26—H26B	109.5	H53B—C53—H53C	109.5
C23—C26—H26C	109.5	C50—C54—H54A	109.5
H26A—C26—H26C	109.5	C50—C54—H54B	109.5
H26B—C26—H26C	109.5	H54A—C54—H54B	109.5
C25—C27—H27A	109.5	C50—C54—H54C	109.5
C25—C27—H27B	109.5	H54A—C54—H54C	109.5
H27A—C27—H27B	109.5	H54B—C54—H54C	109.5
C2—N2—C1—N1	−1.1 (5)	C29—N4—C28—N6	1.7 (5)
C2—N2—C1—C4	−178.3 (3)	C29—N4—C28—C31	−173.6 (3)
C3—N1—C1—N2	1.7 (5)	C30—N6—C28—N4	−0.6 (5)
C3—N1—C1—C4	178.9 (3)	C30—N6—C28—C31	174.8 (3)
C1—N2—C2—N3	−0.9 (5)	C28—N4—C29—N5	−1.4 (5)
C1—N2—C2—C12	175.1 (3)	C28—N4—C29—C47	179.1 (3)
C3—N3—C2—N2	1.9 (5)	C30—N5—C29—N4	0.0 (4)
C3—N3—C2—C12	−174.0 (3)	C30—N5—C29—C47	179.5 (3)
C1—N1—C3—N3	−0.5 (5)	C28—N6—C30—N5	−1.0 (5)
C1—N1—C3—C20	178.5 (3)	C28—N6—C30—C39	−178.4 (3)
C2—N3—C3—N1	−1.1 (5)	C29—N5—C30—N6	1.2 (5)
C2—N3—C3—C20	179.8 (3)	C29—N5—C30—C39	178.6 (3)
N2—C1—C4—C9	28.5 (4)	N4—C28—C31—C36	154.1 (3)
N1—C1—C4—C9	−148.9 (3)	N6—C28—C31—C36	−21.6 (5)
N2—C1—C4—C5	−151.8 (3)	N4—C28—C31—C32	−21.5 (5)
N1—C1—C4—C5	30.8 (5)	N6—C28—C31—C32	162.8 (3)
C9—C4—C5—C6	2.2 (5)	C36—C31—C32—C33	−4.2 (5)
C1—C4—C5—C6	−177.5 (3)	C28—C31—C32—C33	171.3 (3)
C9—C4—C5—C10	−175.7 (3)	C36—C31—C32—C37	174.0 (3)
C1—C4—C5—C10	4.6 (5)	C28—C31—C32—C37	−10.5 (5)
C4—C5—C6—C7	−0.2 (5)	C31—C32—C33—C34	1.1 (5)
C10—C5—C6—C7	177.9 (3)	C37—C32—C33—C34	−177.2 (3)
C5—C6—C7—C8	−1.8 (5)	C32—C33—C34—C35	2.4 (5)
C5—C6—C7—C11	176.8 (3)	C32—C33—C34—C38	−177.3 (3)
C6—C7—C8—C9	1.7 (5)	C33—C34—C35—C36	−2.6 (5)
C11—C7—C8—C9	−176.8 (3)	C38—C34—C35—C36	177.0 (3)
C7—C8—C9—C4	0.3 (5)	C34—C35—C36—C31	−0.5 (5)
C5—C4—C9—C8	−2.3 (5)	C32—C31—C36—C35	4.0 (5)
C1—C4—C9—C8	177.5 (3)	C28—C31—C36—C35	−171.8 (3)
N2—C2—C12—C13	−23.1 (4)	N6—C30—C39—C44	−151.5 (3)
N3—C2—C12—C13	153.1 (3)	N5—C30—C39—C44	30.9 (5)
N2—C2—C12—C17	160.4 (3)	N6—C30—C39—C40	30.1 (4)
N3—C2—C12—C17	−23.3 (5)	N5—C30—C39—C40	−147.5 (3)
C17—C12—C13—C14	3.9 (5)	C44—C39—C40—C41	−3.4 (5)
C2—C12—C13—C14	−172.8 (3)	C30—C39—C40—C41	175.1 (3)
C12—C13—C14—C15	−0.7 (5)	C39—C40—C41—C42	1.2 (5)
C13—C14—C15—C16	−2.6 (5)	C40—C41—C42—C43	2.1 (5)
C13—C14—C15—C18	177.5 (3)	C40—C41—C42—C45	−175.9 (3)
C14—C15—C16—C17	2.8 (5)	C41—C42—C43—C44	−3.2 (5)
C18—C15—C16—C17	−177.4 (3)	C45—C42—C43—C44	174.8 (3)
C15—C16—C17—C12	0.4 (5)	C40—C39—C44—C43	2.3 (5)
C15—C16—C17—C19	−177.7 (3)	C30—C39—C44—C43	−176.1 (3)
C13—C12—C17—C16	−3.6 (5)	C40—C39—C44—C46	−176.4 (3)
C2—C12—C17—C16	172.7 (3)	C30—C39—C44—C46	5.2 (5)
C13—C12—C17—C19	174.3 (3)	C42—C43—C44—C39	1.0 (5)
C2—C12—C17—C19	−9.3 (5)	C42—C43—C44—C46	179.8 (3)
N1—C3—C20—C21	−158.5 (3)	N4—C29—C47—C48	−159.9 (3)
N3—C3—C20—C21	20.7 (4)	N5—C29—C47—C48	20.6 (5)
N1—C3—C20—C25	20.3 (5)	N4—C29—C47—C52	20.1 (4)
N3—C3—C20—C25	−160.5 (3)	N5—C29—C47—C52	−159.5 (3)
C25—C20—C21—C22	−1.6 (5)	C52—C47—C48—C49	2.3 (5)
C3—C20—C21—C22	177.2 (3)	C29—C47—C48—C49	−177.7 (3)
C20—C21—C22—C23	−0.1 (5)	C52—C47—C48—C53	−176.0 (3)
C21—C22—C23—C24	1.5 (5)	C29—C47—C48—C53	3.9 (5)
C21—C22—C23—C26	−177.2 (3)	C47—C48—C49—C50	−0.3 (5)
C22—C23—C24—C25	−1.2 (5)	C53—C48—C49—C50	178.2 (3)
C26—C23—C24—C25	177.5 (3)	C48—C49—C50—C51	−1.7 (5)
C23—C24—C25—C20	−0.6 (5)	C48—C49—C50—C54	177.3 (3)
C23—C24—C25—C27	177.4 (3)	C49—C50—C51—C52	1.7 (5)
C21—C20—C25—C24	1.9 (5)	C54—C50—C51—C52	−177.3 (3)
C3—C20—C25—C24	−176.9 (3)	C50—C51—C52—C47	0.3 (5)
C21—C20—C25—C27	−175.8 (3)	C48—C47—C52—C51	−2.4 (5)
C3—C20—C25—C27	5.4 (5)	C29—C47—C52—C51	177.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···Cg1i	0.98	2.97	3.777 (4)	140
C18—H18B···Cg2ii	0.98	2.91	3.688 (4)	137
C38—H38C···Cg3iii	0.98	2.84	3.756 (4)	155
C45—H45B···Cg4iv	0.98	2.77	3.596 (4)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1–Cg4 are the centroids of the C39–C44, C31–C36, C12–C17 and C4–C9 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯Cg1i	0.98	2.97	3.777 (4)	140
C18—H18B⋯Cg2ii	0.98	2.91	3.688 (4)	137
C38—H38C⋯Cg3iii	0.98	2.84	3.756 (4)	155
C45—H45B⋯Cg4iv	0.98	2.77	3.596 (4)	142

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