4-[4-(Azido­meth­yl)phen­yl]-2,6-di­phenyl­pyridine

Cheng, X.; Du, Y.; Guo, H.; Chen, Z.; Tian, Y.

doi:10.1107/S2414314619002955

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 4| April 2019| x190295

https://doi.org/10.1107/S2414314619002955

Open

access

4-[4-(Azidomethyl)phenyl]-2,6-diphenylpyridine

Xingwang Cheng,^a Yanan Du,^a Hui Guo,^a Zhiyuan Chen ^a and Yupeng Tian ^a ^*

^aDepartment of Chemistry, Anhui University, Hefei 230601, People's Republic of China
^*Correspondence e-mail: yptian@ahu.edu.cn

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 6 December 2018; accepted 26 February 2019; online 5 April 2019)

The title compound, C₂₄H₁₈N₄, crystallizes with three molecules in the asymmetric unit. In the crystal, weak C—H⋯π interactions link the molecules.

Keywords: crystal structure; azide.

CCDC reference: 1899622

Structure description

Derivatives of the title compound can be used as coordinating ligands in metal complexes (Ai et al., 2016 ; Fernandez-Cestau et al., 2017 ). Herein we report the crystal structure of the title compound (Fig. 1), which crystallizes with three molecules, A (containing N1), B (containing N4) and C (containing N9), in the asymmetric unit. In molecule A, the dihedral angles between the pyridine ring and its ortho phenyl substituents are 14.0 (2) and 22.86 (18)°; the dihedral angle between the pyridine ring and the para-substituent phenyl ring is 9.17 (18)° and the C13—C24—N2—N3 torsion angle for the linkage of the azide group to the aromatic ring is 47.0 (4)°. Equivalent data for molecule B are 5.75 (19), 22.37 (18), 23.39 (17) and 65.5 (4)°, respectively. The equivalent angles for molecule C are 7.5 (2), 22.57 (19), 27.31 (18) and 57.3 (5)°, respectively. In the crystal, weak C—H⋯π interactions link the molecules (Table 1, Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

Cg4, Cg7, Cg8 and Cg11 are the centroids of the C18–C23, C34–C39, C42–C47 and C58–C63 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯Cg8ⁱ	0.93	2.92	3.601 (4)	132
C21—H21⋯Cg7ⁱⁱ	0.93	2.78	3.668 (4)	161
C24—H24B⋯Cg11ⁱⁱⁱ	0.93	2.84	3.443 (5)	121
C36—H36⋯Cg4	0.93	2.82	3.601 (4)	142
Symmetry codes: (i) x, y, z+1; (ii) $[x, -y, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z.

Figure 1
The molecular structure of the title molecule with displacement ellipsoids drawn at the 30% probability level. All H atoms are omitted for clarity.

Figure 2
Partial packing diagram of the title compound. Some short C—H⋯N contacts are indicated by dashed lines.

Synthesis and crystallization

Sodium azide (0.70 g 100 mmol) was added to a solution of [4-(bromomethyl)phenyl]-2,6-diphenylpyridine (4.00 g, 10 mmol) in DMSO (20 ml). The reaction mixture was stirred for 24 h at room temperature. After completion, the mixture was poured into ice–water and a white solid precipitate appeared. The generated crude product was washed with water and recrystallized from ethanol solution to afford colourless blocks. ¹H NMR (400 MHz, DMSO) δ 8.34 (d, J = 7.5 Hz, 4H), 8.30–8.16 (m, 4H), 7.78–7.80 (d, J = 8, 2H), 7.50–7.60 (m, 6H), 4.77 (s, 18H), 4.67 (s, 2H).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₄H₁₈N₄
M_r	362.42
Crystal system, space group	Monoclinic, Pc
Temperature (K)	298
a, b, c (Å)	12.8109 (13), 19.708 (2), 11.4152 (12)
β (°)	108.649 (1)
V (Å³)	2730.8 (5)
Z	6
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD
No. of measured, independent and observed [I > 2σ(I)] reflections	19076, 9342, 8030
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.105, 1.05
No. of reflections	9342
No. of parameters	757
No. of restraints	8
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19
Computer programs: SMART and SAINT (Bruker, 1997 ), SHELXS97 and SHELXTL (Sheldrick, 2008 ) and SHELXL2014 (Sheldrick, 2015 ).

Structural data

CCDC reference: 1899622

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002955/hb4273sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002955/hb4273Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619002955/hb4273Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

4-[4-(Azidomethyl)phenyl]-2,6-diphenylpyridine top

Crystal data top

C₂₄H₁₈N₄	F(000) = 1140
M_r = 362.42	D_x = 1.322 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
a = 12.8109 (13) Å	Cell parameters from 6582 reflections
b = 19.708 (2) Å	θ = 2.3–26.0°
c = 11.4152 (12) Å	µ = 0.08 mm⁻¹
β = 108.649 (1)°	T = 298 K
V = 2730.8 (5) Å³	Block, colourless
Z = 6	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	R_int = 0.029
ω scans	θ_max = 25.0°, θ_min = 1.0°
19076 measured reflections	h = −15→15
9342 independent reflections	k = −23→23
8030 reflections with I > 2σ(I)	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0486P)² + 0.3774P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
9342 reflections	Δρ_max = 0.17 e Å⁻³
757 parameters	Δρ_min = −0.19 e Å⁻³
8 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2172 (4)	0.14940 (19)	0.1061 (4)	0.0420 (10)
H1	0.2426	0.1130	0.1594	0.050*
C2	0.2083 (4)	0.1427 (2)	−0.0169 (4)	0.0481 (11)
H2	0.2269	0.1017	−0.0454	0.058*
C3	0.1721 (3)	0.1959 (2)	−0.0979 (4)	0.0398 (9)
H3	0.1648	0.1911	−0.1812	0.048*
C4	0.1470 (4)	0.2561 (2)	−0.0532 (4)	0.0452 (10)
H4	0.1242	0.2929	−0.1064	0.054*
C5	0.1549 (4)	0.26297 (19)	0.0691 (4)	0.0394 (9)
H5	0.1371	0.3043	0.0970	0.047*
C6	0.1891 (3)	0.20950 (17)	0.1521 (3)	0.0295 (8)
C7	0.1918 (3)	0.21537 (16)	0.2831 (3)	0.0282 (8)
C8	0.1415 (3)	0.26991 (17)	0.3216 (3)	0.0302 (8)
H8	0.1103	0.3046	0.2663	0.036*
C9	0.1373 (3)	0.27298 (17)	0.4408 (3)	0.0285 (8)
C10	0.0784 (3)	0.32896 (16)	0.4812 (3)	0.0281 (8)
C11	0.0137 (3)	0.37504 (17)	0.3968 (4)	0.0332 (9)
H11	0.0115	0.3729	0.3147	0.040*
C12	−0.0475 (3)	0.42398 (18)	0.4320 (4)	0.0365 (9)
H12	−0.0915	0.4532	0.3727	0.044*
C13	−0.0447 (3)	0.43036 (17)	0.5531 (4)	0.0330 (9)
C14	0.0220 (3)	0.38596 (18)	0.6395 (4)	0.0354 (9)
H14	0.0266	0.3898	0.7222	0.043*
C15	0.0818 (3)	0.33614 (18)	0.6041 (3)	0.0336 (9)
H15	0.1253	0.3067	0.6635	0.040*
C16	0.1883 (3)	0.22085 (16)	0.5201 (3)	0.0290 (8)
H16	0.1869	0.2206	0.6011	0.035*
C17	0.2414 (3)	0.16893 (16)	0.4790 (3)	0.0280 (8)
C18	0.3011 (3)	0.11430 (17)	0.5659 (3)	0.0298 (8)
C19	0.3390 (3)	0.12554 (18)	0.6924 (3)	0.0350 (9)
H19	0.3276	0.1675	0.7234	0.042*
C20	0.3938 (3)	0.07480 (19)	0.7735 (4)	0.0385 (9)
H20	0.4185	0.0830	0.8582	0.046*
C21	0.4117 (3)	0.01249 (19)	0.7287 (4)	0.0408 (10)
H21	0.4473	−0.0217	0.7830	0.049*
C22	0.3763 (3)	0.00117 (18)	0.6028 (4)	0.0401 (10)
H22	0.3896	−0.0406	0.5723	0.048*
C23	0.3213 (3)	0.05130 (17)	0.5216 (4)	0.0347 (9)
H23	0.2977	0.0430	0.4370	0.042*
C24	−0.1127 (4)	0.48394 (17)	0.5891 (4)	0.0449 (11)
H24A	−0.1833	0.4876	0.5246	0.054*
H24B	−0.1264	0.4699	0.6644	0.054*
C25	0.2984 (3)	0.43191 (19)	0.1563 (4)	0.0417 (10)
H25	0.3011	0.4290	0.0760	0.050*
C26	0.2404 (4)	0.4843 (2)	0.1881 (4)	0.0469 (11)
H26	0.2041	0.5159	0.1286	0.056*
C27	0.2359 (3)	0.49014 (19)	0.3063 (4)	0.0408 (10)
H27	0.1979	0.5258	0.3274	0.049*
C28	0.2883 (4)	0.4427 (2)	0.3926 (4)	0.0465 (11)
H28	0.2851	0.4458	0.4726	0.056*
C29	0.3462 (4)	0.3899 (2)	0.3618 (4)	0.0418 (10)
H29	0.3812	0.3582	0.4218	0.050*
C30	0.3528 (3)	0.38354 (17)	0.2436 (3)	0.0291 (8)
C31	0.4136 (3)	0.32597 (17)	0.2091 (3)	0.0281 (8)
C32	0.4599 (3)	0.27377 (16)	0.2895 (3)	0.0276 (8)
H32	0.4563	0.2748	0.3696	0.033*
C33	0.5118 (3)	0.21960 (16)	0.2524 (3)	0.0266 (8)
C34	0.5617 (3)	0.16276 (16)	0.3367 (3)	0.0255 (7)
C35	0.5280 (3)	0.14773 (17)	0.4389 (3)	0.0303 (8)
H35	0.4726	0.1735	0.4532	0.036*
C36	0.5752 (3)	0.09545 (17)	0.5191 (3)	0.0313 (8)
H36	0.5509	0.0865	0.5861	0.038*
C37	0.6585 (3)	0.05612 (16)	0.5004 (3)	0.0297 (8)
C38	0.6941 (3)	0.07155 (16)	0.4004 (3)	0.0314 (8)
H38	0.7511	0.0466	0.3876	0.038*
C39	0.6457 (3)	0.12352 (16)	0.3199 (3)	0.0275 (8)
H39	0.6700	0.1323	0.2529	0.033*
C40	0.5136 (3)	0.22171 (18)	0.1312 (3)	0.0304 (8)
H40	0.5455	0.1862	0.1011	0.036*
C41	0.4683 (3)	0.27611 (17)	0.0548 (3)	0.0284 (8)
C42	0.4702 (3)	0.28054 (17)	−0.0749 (3)	0.0314 (8)
C43	0.5484 (3)	0.24521 (17)	−0.1117 (3)	0.0330 (8)
H43	0.6002	0.2184	−0.0549	0.040*
C44	0.5495 (3)	0.24965 (17)	−0.2323 (4)	0.0375 (9)
H44	0.6027	0.2262	−0.2557	0.045*
C45	0.4726 (3)	0.28851 (18)	−0.3180 (4)	0.0395 (9)
H45	0.4728	0.2906	−0.3993	0.047*
C46	0.3953 (3)	0.32442 (19)	−0.2822 (4)	0.0395 (10)
H46	0.3439	0.3513	−0.3393	0.047*
C47	0.3941 (3)	0.32042 (19)	−0.1620 (3)	0.0370 (9)
H47	0.3416	0.3447	−0.1388	0.044*
C48	0.7046 (3)	−0.00393 (18)	0.5824 (4)	0.0361 (9)
H48A	0.7833	−0.0069	0.5966	0.043*
H48B	0.6935	0.0027	0.6618	0.043*
C49	0.9052 (3)	0.1648 (2)	0.2320 (4)	0.0387 (9)
H49	0.9288	0.1282	0.2855	0.046*
C50	0.9134 (4)	0.1616 (2)	0.1147 (4)	0.0445 (10)
H50	0.9431	0.1230	0.0903	0.053*
C51	0.8786 (4)	0.2142 (2)	0.0336 (4)	0.0476 (11)
H51	0.8849	0.2117	−0.0453	0.057*
C52	0.8342 (4)	0.2709 (2)	0.0696 (4)	0.0491 (11)
H52	0.8094	0.3068	0.0148	0.059*
C53	0.8264 (4)	0.2744 (2)	0.1876 (4)	0.0444 (10)
H53	0.7963	0.3129	0.2111	0.053*
C54	0.8622 (3)	0.22190 (17)	0.2714 (3)	0.0319 (8)
C55	0.8566 (3)	0.22446 (17)	0.3994 (3)	0.0293 (8)
C56	0.8022 (3)	0.27609 (18)	0.4407 (3)	0.0317 (8)
H56	0.7687	0.3112	0.3876	0.038*
C57	0.7978 (3)	0.27529 (17)	0.5605 (3)	0.0293 (8)
C58	0.7436 (3)	0.33115 (17)	0.6084 (3)	0.0315 (8)
C59	0.6588 (3)	0.36879 (18)	0.5300 (4)	0.0349 (9)
H59	0.6351	0.3595	0.4457	0.042*
C60	0.6084 (3)	0.42047 (18)	0.5757 (4)	0.0374 (9)
H60	0.5511	0.4451	0.5216	0.045*
C61	0.6424 (3)	0.43557 (19)	0.7004 (4)	0.0380 (9)
C62	0.7273 (3)	0.39818 (19)	0.7786 (4)	0.0387 (9)
H62	0.7508	0.4076	0.8628	0.046*
C63	0.7779 (3)	0.34714 (18)	0.7345 (3)	0.0346 (9)
H63	0.8354	0.3230	0.7891	0.042*
C64	0.8480 (3)	0.22099 (18)	0.6349 (3)	0.0318 (9)
H64	0.8460	0.2180	0.7155	0.038*
C65	0.9012 (3)	0.17099 (17)	0.5890 (3)	0.0307 (8)
C66	0.9547 (3)	0.11118 (17)	0.6645 (3)	0.0323 (8)
C67	0.9254 (3)	0.08887 (19)	0.7661 (4)	0.0364 (9)
H67	0.8723	0.1124	0.7895	0.044*
C68	0.9745 (3)	0.0323 (2)	0.8316 (4)	0.0433 (10)
H68	0.9534	0.0177	0.8981	0.052*
C69	1.0544 (4)	−0.0027 (2)	0.8002 (4)	0.0507 (12)
H69	1.0873	−0.0408	0.8449	0.061*
C70	1.0847 (4)	0.0194 (2)	0.7014 (4)	0.0484 (11)
H70	1.1392	−0.0037	0.6800	0.058*
C71	1.0355 (3)	0.07546 (19)	0.6336 (4)	0.0404 (10)
H71	1.0566	0.0894	0.5667	0.048*
C72	0.5887 (4)	0.4925 (2)	0.7489 (4)	0.0516 (11)
H72A	0.5116	0.4954	0.6993	0.062*
H72B	0.5922	0.4823	0.8333	0.062*
N1	0.2418 (2)	0.16545 (14)	0.3615 (3)	0.0303 (7)
N2	−0.0585 (3)	0.55181 (17)	0.6094 (3)	0.0498 (9)
N3	−0.0203 (3)	0.57001 (16)	0.5287 (3)	0.0466 (9)
N4	0.0178 (4)	0.5914 (2)	0.4591 (4)	0.0671 (12)
N5	0.4189 (2)	0.32805 (14)	0.0933 (3)	0.0309 (7)
N6	0.6509 (3)	−0.06933 (14)	0.5263 (3)	0.0352 (7)
N7	0.6711 (3)	−0.08424 (14)	0.4303 (3)	0.0345 (7)
N8	0.6842 (3)	−0.10260 (16)	0.3418 (3)	0.0436 (8)
N9	0.9067 (2)	0.17328 (15)	0.4743 (3)	0.0318 (7)
N10	0.6430 (3)	0.55916 (18)	0.7462 (4)	0.0554 (10)
N11	0.6441 (3)	0.57498 (17)	0.6416 (4)	0.0494 (9)
N12	0.6505 (4)	0.59316 (19)	0.5491 (4)	0.0660 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.057 (3)	0.032 (2)	0.039 (3)	0.0068 (19)	0.019 (2)	0.0018 (18)
C2	0.068 (3)	0.037 (2)	0.043 (3)	0.004 (2)	0.023 (2)	−0.0092 (19)
C3	0.045 (2)	0.047 (2)	0.028 (2)	−0.0054 (19)	0.0125 (19)	−0.0090 (18)
C4	0.058 (3)	0.045 (2)	0.033 (3)	0.007 (2)	0.016 (2)	0.0044 (19)
C5	0.057 (3)	0.032 (2)	0.030 (2)	0.0045 (18)	0.016 (2)	−0.0025 (17)
C6	0.0280 (19)	0.0269 (17)	0.032 (2)	−0.0027 (14)	0.0077 (16)	−0.0016 (15)
C7	0.0273 (19)	0.0264 (17)	0.030 (2)	−0.0031 (14)	0.0082 (16)	0.0004 (15)
C8	0.033 (2)	0.0265 (17)	0.030 (2)	0.0022 (15)	0.0085 (17)	0.0046 (15)
C9	0.029 (2)	0.0256 (17)	0.030 (2)	−0.0039 (14)	0.0086 (17)	−0.0002 (15)
C10	0.0297 (19)	0.0245 (17)	0.030 (2)	−0.0035 (14)	0.0100 (16)	−0.0010 (15)
C11	0.048 (2)	0.0289 (17)	0.025 (2)	0.0019 (16)	0.0159 (18)	0.0029 (15)
C12	0.044 (2)	0.0291 (19)	0.036 (2)	0.0043 (16)	0.0124 (19)	0.0053 (17)
C13	0.042 (2)	0.0254 (17)	0.035 (2)	−0.0045 (16)	0.0169 (18)	−0.0022 (16)
C14	0.047 (2)	0.0317 (19)	0.030 (2)	−0.0041 (17)	0.0171 (19)	−0.0015 (16)
C15	0.037 (2)	0.0302 (19)	0.032 (2)	0.0015 (16)	0.0098 (18)	0.0045 (16)
C16	0.033 (2)	0.0305 (18)	0.024 (2)	−0.0016 (15)	0.0093 (16)	0.0004 (15)
C17	0.028 (2)	0.0257 (17)	0.030 (2)	−0.0020 (14)	0.0092 (17)	0.0014 (15)
C18	0.031 (2)	0.0280 (17)	0.031 (2)	0.0000 (15)	0.0111 (17)	0.0026 (15)
C19	0.040 (2)	0.0326 (19)	0.035 (2)	0.0005 (16)	0.0148 (19)	0.0033 (17)
C20	0.035 (2)	0.045 (2)	0.033 (2)	0.0008 (17)	0.0075 (18)	0.0102 (18)
C21	0.039 (2)	0.036 (2)	0.045 (3)	0.0025 (17)	0.012 (2)	0.0166 (19)
C22	0.040 (2)	0.0289 (19)	0.051 (3)	0.0025 (17)	0.015 (2)	0.0057 (18)
C23	0.036 (2)	0.0313 (19)	0.036 (2)	−0.0008 (16)	0.0110 (18)	0.0022 (16)
C24	0.061 (3)	0.0301 (19)	0.055 (3)	0.0033 (19)	0.034 (2)	0.0021 (18)
C25	0.054 (3)	0.044 (2)	0.035 (2)	0.0071 (19)	0.025 (2)	0.0055 (19)
C26	0.059 (3)	0.040 (2)	0.049 (3)	0.016 (2)	0.026 (2)	0.015 (2)
C27	0.047 (2)	0.036 (2)	0.044 (3)	0.0075 (18)	0.021 (2)	−0.0029 (18)
C28	0.067 (3)	0.048 (2)	0.029 (2)	0.014 (2)	0.022 (2)	−0.0037 (19)
C29	0.058 (3)	0.039 (2)	0.028 (2)	0.0107 (19)	0.013 (2)	0.0027 (17)
C30	0.031 (2)	0.0304 (18)	0.026 (2)	−0.0042 (15)	0.0098 (16)	0.0021 (15)
C31	0.029 (2)	0.0280 (18)	0.026 (2)	−0.0040 (14)	0.0075 (16)	−0.0010 (15)
C32	0.031 (2)	0.0305 (17)	0.020 (2)	−0.0032 (15)	0.0068 (15)	−0.0030 (15)
C33	0.028 (2)	0.0277 (17)	0.024 (2)	−0.0055 (14)	0.0090 (16)	−0.0022 (15)
C34	0.0298 (19)	0.0262 (16)	0.0190 (19)	−0.0062 (14)	0.0058 (15)	−0.0025 (14)
C35	0.035 (2)	0.0321 (18)	0.025 (2)	−0.0019 (16)	0.0118 (17)	−0.0028 (15)
C36	0.040 (2)	0.0342 (19)	0.022 (2)	−0.0053 (16)	0.0133 (17)	0.0024 (16)
C37	0.034 (2)	0.0280 (17)	0.024 (2)	−0.0056 (15)	0.0037 (16)	−0.0021 (15)
C38	0.031 (2)	0.0259 (17)	0.037 (2)	−0.0040 (15)	0.0096 (17)	−0.0049 (16)
C39	0.032 (2)	0.0281 (17)	0.024 (2)	−0.0049 (15)	0.0108 (16)	0.0011 (15)
C40	0.036 (2)	0.0305 (19)	0.026 (2)	−0.0023 (15)	0.0129 (17)	−0.0024 (15)
C41	0.034 (2)	0.0299 (18)	0.021 (2)	−0.0034 (15)	0.0087 (16)	−0.0009 (15)
C42	0.038 (2)	0.0283 (18)	0.027 (2)	−0.0036 (16)	0.0099 (17)	0.0014 (16)
C43	0.042 (2)	0.0297 (18)	0.029 (2)	0.0023 (16)	0.0141 (18)	0.0025 (16)
C44	0.051 (2)	0.0297 (19)	0.038 (3)	0.0014 (17)	0.023 (2)	0.0020 (17)
C45	0.057 (3)	0.038 (2)	0.028 (2)	−0.0071 (19)	0.020 (2)	0.0029 (17)
C46	0.046 (2)	0.040 (2)	0.030 (2)	0.0017 (18)	0.0093 (19)	0.0113 (18)
C47	0.044 (2)	0.038 (2)	0.030 (2)	0.0033 (17)	0.0133 (18)	0.0025 (17)
C48	0.047 (2)	0.0342 (19)	0.023 (2)	−0.0016 (17)	0.0063 (18)	−0.0014 (16)
C49	0.047 (2)	0.040 (2)	0.032 (2)	−0.0073 (18)	0.0168 (19)	−0.0054 (18)
C50	0.056 (3)	0.042 (2)	0.041 (3)	−0.0069 (19)	0.023 (2)	−0.0104 (19)
C51	0.057 (3)	0.059 (3)	0.030 (3)	−0.017 (2)	0.018 (2)	−0.010 (2)
C52	0.072 (3)	0.048 (2)	0.026 (2)	−0.002 (2)	0.015 (2)	0.0016 (19)
C53	0.056 (3)	0.045 (2)	0.032 (3)	0.002 (2)	0.014 (2)	−0.0033 (19)
C54	0.035 (2)	0.0339 (19)	0.028 (2)	−0.0106 (16)	0.0114 (17)	−0.0058 (16)
C55	0.033 (2)	0.0321 (18)	0.024 (2)	−0.0128 (15)	0.0111 (17)	−0.0048 (15)
C56	0.036 (2)	0.0314 (18)	0.029 (2)	−0.0071 (15)	0.0115 (17)	−0.0007 (15)
C57	0.033 (2)	0.0271 (18)	0.029 (2)	−0.0095 (15)	0.0112 (17)	−0.0033 (15)
C58	0.036 (2)	0.0312 (18)	0.031 (2)	−0.0071 (16)	0.0161 (18)	−0.0003 (16)
C59	0.039 (2)	0.0355 (19)	0.031 (2)	−0.0091 (17)	0.0128 (18)	−0.0019 (17)
C60	0.039 (2)	0.0345 (19)	0.041 (3)	0.0003 (16)	0.0155 (19)	0.0024 (18)
C61	0.046 (2)	0.037 (2)	0.036 (3)	−0.0018 (18)	0.0202 (19)	0.0006 (18)
C62	0.053 (3)	0.039 (2)	0.027 (2)	−0.0014 (19)	0.0159 (19)	−0.0023 (17)
C63	0.044 (2)	0.038 (2)	0.025 (2)	−0.0015 (17)	0.0148 (18)	−0.0006 (16)
C64	0.042 (2)	0.0336 (19)	0.023 (2)	−0.0089 (16)	0.0149 (17)	−0.0045 (16)
C65	0.031 (2)	0.0333 (18)	0.029 (2)	−0.0104 (15)	0.0118 (17)	−0.0052 (16)
C66	0.033 (2)	0.0334 (18)	0.029 (2)	−0.0065 (16)	0.0074 (17)	−0.0021 (16)
C67	0.038 (2)	0.039 (2)	0.032 (2)	−0.0038 (17)	0.0102 (18)	0.0015 (17)
C68	0.046 (2)	0.043 (2)	0.039 (3)	−0.0049 (19)	0.010 (2)	0.0073 (19)
C69	0.045 (3)	0.044 (2)	0.054 (3)	0.003 (2)	0.004 (2)	0.010 (2)
C70	0.047 (3)	0.051 (2)	0.047 (3)	0.007 (2)	0.014 (2)	−0.001 (2)
C71	0.044 (2)	0.041 (2)	0.038 (3)	−0.0016 (18)	0.014 (2)	−0.0049 (18)
C72	0.065 (3)	0.050 (2)	0.049 (3)	0.012 (2)	0.032 (2)	0.004 (2)
N1	0.0308 (17)	0.0278 (15)	0.0316 (19)	0.0000 (12)	0.0089 (14)	0.0016 (13)
N2	0.074 (3)	0.0356 (18)	0.047 (2)	0.0031 (17)	0.029 (2)	−0.0066 (16)
N3	0.064 (2)	0.0297 (17)	0.041 (2)	−0.0036 (16)	0.009 (2)	−0.0019 (16)
N4	0.089 (3)	0.055 (2)	0.053 (3)	−0.026 (2)	0.017 (2)	0.006 (2)
N5	0.0358 (18)	0.0316 (15)	0.0271 (19)	−0.0011 (13)	0.0127 (14)	−0.0010 (13)
N6	0.051 (2)	0.0309 (15)	0.0275 (19)	−0.0013 (14)	0.0172 (15)	0.0010 (13)
N7	0.0389 (18)	0.0263 (15)	0.036 (2)	−0.0037 (13)	0.0095 (16)	0.0056 (14)
N8	0.056 (2)	0.0419 (18)	0.036 (2)	−0.0070 (16)	0.0195 (18)	−0.0035 (16)
N9	0.0331 (17)	0.0348 (16)	0.0277 (18)	−0.0084 (13)	0.0100 (14)	−0.0018 (14)
N10	0.075 (3)	0.047 (2)	0.041 (3)	0.0088 (19)	0.014 (2)	−0.0124 (18)
N11	0.058 (2)	0.0322 (18)	0.059 (3)	0.0063 (16)	0.019 (2)	−0.0081 (18)
N12	0.093 (3)	0.045 (2)	0.071 (3)	0.005 (2)	0.042 (3)	0.002 (2)

Geometric parameters (Å, º) top

C1—C2	1.378 (6)	C38—H38	0.9300
C1—C6	1.389 (5)	C39—H39	0.9300
C1—H1	0.9300	C40—C41	1.387 (5)
C2—C3	1.378 (6)	C40—H40	0.9300
C2—H2	0.9300	C41—N5	1.350 (4)
C3—C4	1.370 (5)	C41—C42	1.491 (5)
C3—H3	0.9300	C42—C47	1.392 (5)
C4—C5	1.373 (6)	C42—C43	1.390 (5)
C4—H4	0.9300	C43—C44	1.384 (5)
C5—C6	1.391 (5)	C43—H43	0.9300
C5—H5	0.9300	C44—C45	1.377 (6)
C6—C7	1.488 (5)	C44—H44	0.9300
C7—N1	1.347 (4)	C45—C46	1.381 (6)
C7—C8	1.395 (5)	C45—H45	0.9300
C8—C9	1.380 (5)	C46—C47	1.379 (5)
C8—H8	0.9300	C46—H46	0.9300
C9—C16	1.387 (5)	C47—H47	0.9300
C9—C10	1.490 (5)	C48—N6	1.505 (5)
C10—C11	1.390 (5)	C48—H48A	0.9700
C10—C15	1.396 (5)	C48—H48B	0.9700
C11—C12	1.381 (5)	C49—C50	1.378 (5)
C11—H11	0.9300	C49—C54	1.390 (5)
C12—C13	1.377 (5)	C49—H49	0.9300
C12—H12	0.9300	C50—C51	1.367 (6)
C13—C14	1.389 (5)	C50—H50	0.9300
C13—C24	1.507 (5)	C51—C52	1.375 (6)
C14—C15	1.383 (5)	C51—H51	0.9300
C14—H14	0.9300	C52—C53	1.383 (6)
C15—H15	0.9300	C52—H52	0.9300
C16—C17	1.391 (5)	C53—C54	1.384 (5)
C16—H16	0.9300	C53—H53	0.9300
C17—N1	1.345 (5)	C54—C55	1.486 (5)
C17—C18	1.497 (5)	C55—N9	1.345 (5)
C18—C19	1.387 (5)	C55—C56	1.398 (5)
C18—C23	1.396 (5)	C56—C57	1.386 (5)
C19—C20	1.391 (5)	C56—H56	0.9300
C19—H19	0.9300	C57—C64	1.389 (5)
C20—C21	1.377 (5)	C57—C58	1.495 (5)
C20—H20	0.9300	C58—C59	1.382 (5)
C21—C22	1.380 (6)	C58—C63	1.400 (5)
C21—H21	0.9300	C59—C60	1.394 (5)
C22—C23	1.384 (5)	C59—H59	0.9300
C22—H22	0.9300	C60—C61	1.381 (6)
C23—H23	0.9300	C60—H60	0.9300
C24—N2	1.490 (5)	C61—C62	1.379 (6)
C24—H24A	0.9700	C61—C72	1.511 (5)
C24—H24B	0.9700	C62—C63	1.376 (5)
C25—C26	1.387 (5)	C62—H62	0.9300
C25—C30	1.393 (5)	C63—H63	0.9300
C25—H25	0.9300	C64—C65	1.392 (5)
C26—C27	1.373 (6)	C64—H64	0.9300
C26—H26	0.9300	C65—N9	1.335 (4)
C27—C28	1.369 (6)	C65—C66	1.491 (5)
C27—H27	0.9300	C66—C71	1.387 (5)
C28—C29	1.385 (5)	C66—C67	1.399 (5)
C28—H28	0.9300	C67—C68	1.377 (5)
C29—C30	1.385 (5)	C67—H67	0.9300
C29—H29	0.9300	C68—C69	1.373 (6)
C30—C31	1.499 (5)	C68—H68	0.9300
C31—N5	1.345 (4)	C69—C70	1.377 (6)
C31—C32	1.380 (5)	C69—H69	0.9300
C32—C33	1.393 (5)	C70—C71	1.380 (6)
C32—H32	0.9300	C70—H70	0.9300
C33—C40	1.392 (5)	C71—H71	0.9300
C33—C34	1.482 (5)	C72—N10	1.492 (6)
C34—C39	1.387 (5)	C72—H72A	0.9700
C34—C35	1.399 (5)	C72—H72B	0.9700
C35—C36	1.383 (5)	N2—N3	1.227 (5)
C35—H35	0.9300	N3—N4	1.139 (5)
C36—C37	1.390 (5)	N6—N7	1.238 (4)
C36—H36	0.9300	N7—N8	1.135 (4)
C37—C38	1.391 (5)	N10—N11	1.238 (5)
C37—C48	1.508 (5)	N11—N12	1.143 (5)
C38—C39	1.383 (5)

C2—C1—C6	121.3 (4)	C38—C39—C34	121.6 (3)
C2—C1—H1	119.3	C38—C39—H39	119.2
C6—C1—H1	119.3	C34—C39—H39	119.2
C1—C2—C3	120.8 (4)	C41—C40—C33	120.8 (3)
C1—C2—H2	119.6	C41—C40—H40	119.6
C3—C2—H2	119.6	C33—C40—H40	119.6
C4—C3—C2	118.5 (4)	N5—C41—C40	121.8 (3)
C4—C3—H3	120.7	N5—C41—C42	116.0 (3)
C2—C3—H3	120.7	C40—C41—C42	122.3 (3)
C3—C4—C5	120.9 (4)	C47—C42—C43	118.4 (3)
C3—C4—H4	119.5	C47—C42—C41	120.8 (3)
C5—C4—H4	119.5	C43—C42—C41	120.8 (3)
C4—C5—C6	121.5 (4)	C44—C43—C42	120.4 (4)
C4—C5—H5	119.2	C44—C43—H43	119.8
C6—C5—H5	119.2	C42—C43—H43	119.8
C1—C6—C5	116.8 (3)	C45—C44—C43	120.6 (4)
C1—C6—C7	121.4 (3)	C45—C44—H44	119.7
C5—C6—C7	121.8 (3)	C43—C44—H44	119.7
N1—C7—C8	121.5 (3)	C44—C45—C46	119.5 (4)
N1—C7—C6	117.7 (3)	C44—C45—H45	120.2
C8—C7—C6	120.8 (3)	C46—C45—H45	120.2
C9—C8—C7	120.8 (3)	C47—C46—C45	120.1 (4)
C9—C8—H8	119.6	C47—C46—H46	119.9
C7—C8—H8	119.6	C45—C46—H46	119.9
C8—C9—C16	116.9 (3)	C46—C47—C42	121.0 (4)
C8—C9—C10	121.4 (3)	C46—C47—H47	119.5
C16—C9—C10	121.7 (3)	C42—C47—H47	119.5
C11—C10—C15	116.8 (3)	N6—C48—C37	111.9 (3)
C11—C10—C9	121.2 (3)	N6—C48—H48A	109.2
C15—C10—C9	122.0 (3)	C37—C48—H48A	109.2
C12—C11—C10	121.5 (4)	N6—C48—H48B	109.2
C12—C11—H11	119.2	C37—C48—H48B	109.2
C10—C11—H11	119.2	H48A—C48—H48B	107.9
C13—C12—C11	121.4 (4)	C50—C49—C54	120.9 (4)
C13—C12—H12	119.3	C50—C49—H49	119.6
C11—C12—H12	119.3	C54—C49—H49	119.6
C12—C13—C14	117.9 (3)	C51—C50—C49	120.9 (4)
C12—C13—C24	120.4 (4)	C51—C50—H50	119.5
C14—C13—C24	121.7 (4)	C49—C50—H50	119.5
C15—C14—C13	120.8 (4)	C50—C51—C52	119.4 (4)
C15—C14—H14	119.6	C50—C51—H51	120.3
C13—C14—H14	119.6	C52—C51—H51	120.3
C14—C15—C10	121.6 (3)	C51—C52—C53	119.8 (4)
C14—C15—H15	119.2	C51—C52—H52	120.1
C10—C15—H15	119.2	C53—C52—H52	120.1
C9—C16—C17	120.3 (3)	C54—C53—C52	121.6 (4)
C9—C16—H16	119.9	C54—C53—H53	119.2
C17—C16—H16	119.9	C52—C53—H53	119.2
N1—C17—C16	122.2 (3)	C53—C54—C49	117.4 (4)
N1—C17—C18	117.4 (3)	C53—C54—C55	123.0 (3)
C16—C17—C18	120.5 (3)	C49—C54—C55	119.6 (3)
C19—C18—C23	118.4 (3)	N9—C55—C56	121.3 (3)
C19—C18—C17	120.6 (3)	N9—C55—C54	115.9 (3)
C23—C18—C17	121.0 (3)	C56—C55—C54	122.9 (3)
C18—C19—C20	120.9 (4)	C57—C56—C55	120.5 (3)
C18—C19—H19	119.6	C57—C56—H56	119.8
C20—C19—H19	119.6	C55—C56—H56	119.8
C21—C20—C19	120.1 (4)	C56—C57—C64	117.1 (3)
C21—C20—H20	119.9	C56—C57—C58	121.5 (3)
C19—C20—H20	119.9	C64—C57—C58	121.4 (3)
C20—C21—C22	119.5 (4)	C59—C58—C63	117.9 (3)
C20—C21—H21	120.2	C59—C58—C57	121.3 (3)
C22—C21—H21	120.2	C63—C58—C57	120.8 (3)
C21—C22—C23	120.7 (4)	C58—C59—C60	120.8 (4)
C21—C22—H22	119.7	C58—C59—H59	119.6
C23—C22—H22	119.7	C60—C59—H59	119.6
C22—C23—C18	120.4 (4)	C61—C60—C59	120.8 (4)
C22—C23—H23	119.8	C61—C60—H60	119.6
C18—C23—H23	119.8	C59—C60—H60	119.6
N2—C24—C13	113.0 (3)	C60—C61—C62	118.4 (4)
N2—C24—H24A	109.0	C60—C61—C72	120.5 (4)
C13—C24—H24A	109.0	C62—C61—C72	121.1 (4)
N2—C24—H24B	109.0	C63—C62—C61	121.3 (4)
C13—C24—H24B	109.0	C63—C62—H62	119.3
H24A—C24—H24B	107.8	C61—C62—H62	119.3
C26—C25—C30	120.6 (4)	C62—C63—C58	120.8 (4)
C26—C25—H25	119.7	C62—C63—H63	119.6
C30—C25—H25	119.7	C58—C63—H63	119.6
C27—C26—C25	120.9 (4)	C57—C64—C65	120.1 (3)
C27—C26—H26	119.5	C57—C64—H64	119.9
C25—C26—H26	119.5	C65—C64—H64	119.9
C28—C27—C26	119.0 (4)	N9—C65—C64	122.1 (3)
C28—C27—H27	120.5	N9—C65—C66	115.7 (3)
C26—C27—H27	120.5	C64—C65—C66	122.2 (3)
C27—C28—C29	120.6 (4)	C71—C66—C67	118.1 (3)
C27—C28—H28	119.7	C71—C66—C65	119.8 (3)
C29—C28—H28	119.7	C67—C66—C65	122.1 (3)
C30—C29—C28	121.3 (4)	C68—C67—C66	120.5 (4)
C30—C29—H29	119.3	C68—C67—H67	119.8
C28—C29—H29	119.3	C66—C67—H67	119.8
C29—C30—C25	117.5 (3)	C69—C68—C67	120.9 (4)
C29—C30—C31	121.6 (3)	C69—C68—H68	119.5
C25—C30—C31	120.9 (3)	C67—C68—H68	119.5
N5—C31—C32	122.1 (3)	C68—C69—C70	118.9 (4)
N5—C31—C30	115.4 (3)	C68—C69—H69	120.5
C32—C31—C30	122.5 (3)	C70—C69—H69	120.5
C31—C32—C33	120.9 (3)	C69—C70—C71	121.0 (4)
C31—C32—H32	119.5	C69—C70—H70	119.5
C33—C32—H32	119.5	C71—C70—H70	119.5
C40—C33—C32	116.2 (3)	C70—C71—C66	120.6 (4)
C40—C33—C34	121.8 (3)	C70—C71—H71	119.7
C32—C33—C34	122.0 (3)	C66—C71—H71	119.7
C39—C34—C35	117.2 (3)	N10—C72—C61	112.1 (3)
C39—C34—C33	121.6 (3)	N10—C72—H72A	109.2
C35—C34—C33	121.1 (3)	C61—C72—H72A	109.2
C36—C35—C34	121.6 (3)	N10—C72—H72B	109.2
C36—C35—H35	119.2	C61—C72—H72B	109.2
C34—C35—H35	119.2	H72A—C72—H72B	107.9
C35—C36—C37	120.5 (3)	C17—N1—C7	118.3 (3)
C35—C36—H36	119.7	N3—N2—C24	115.0 (3)
C37—C36—H36	119.7	N4—N3—N2	174.6 (4)
C38—C37—C36	118.3 (3)	C31—N5—C41	118.2 (3)
C38—C37—C48	121.0 (3)	N7—N6—C48	112.6 (3)
C36—C37—C48	120.6 (3)	N8—N7—N6	174.2 (4)
C39—C38—C37	120.8 (3)	C65—N9—C55	119.0 (3)
C39—C38—H38	119.6	N11—N10—C72	113.0 (3)
C37—C38—H38	119.6	N12—N11—N10	175.0 (5)

C6—C1—C2—C3	0.7 (7)	C33—C40—C41—N5	−1.5 (5)
C1—C2—C3—C4	1.1 (7)	C33—C40—C41—C42	179.1 (3)
C2—C3—C4—C5	−1.6 (6)	N5—C41—C42—C47	−22.3 (5)
C3—C4—C5—C6	0.3 (7)	C40—C41—C42—C47	157.1 (4)
C2—C1—C6—C5	−1.9 (6)	N5—C41—C42—C43	157.4 (3)
C2—C1—C6—C7	176.0 (4)	C40—C41—C42—C43	−23.2 (5)
C4—C5—C6—C1	1.4 (6)	C47—C42—C43—C44	−0.3 (5)
C4—C5—C6—C7	−176.5 (4)	C41—C42—C43—C44	−180.0 (3)
C1—C6—C7—N1	12.3 (5)	C42—C43—C44—C45	−0.7 (5)
C5—C6—C7—N1	−169.9 (3)	C43—C44—C45—C46	1.4 (6)
C1—C6—C7—C8	−166.0 (4)	C44—C45—C46—C47	−1.1 (6)
C5—C6—C7—C8	11.9 (5)	C45—C46—C47—C42	0.1 (6)
N1—C7—C8—C9	−2.7 (5)	C43—C42—C47—C46	0.6 (6)
C6—C7—C8—C9	175.5 (3)	C41—C42—C47—C46	−179.7 (3)
C7—C8—C9—C16	2.0 (5)	C38—C37—C48—N6	−80.7 (4)
C7—C8—C9—C10	−176.6 (3)	C36—C37—C48—N6	96.0 (4)
C8—C9—C10—C11	8.5 (5)	C54—C49—C50—C51	−0.6 (6)
C16—C9—C10—C11	−170.1 (3)	C49—C50—C51—C52	−0.4 (6)
C8—C9—C10—C15	−174.1 (3)	C50—C51—C52—C53	0.7 (7)
C16—C9—C10—C15	7.3 (5)	C51—C52—C53—C54	−0.1 (7)
C15—C10—C11—C12	−2.3 (5)	C52—C53—C54—C49	−0.9 (6)
C9—C10—C11—C12	175.2 (3)	C52—C53—C54—C55	179.0 (4)
C10—C11—C12—C13	1.7 (6)	C50—C49—C54—C53	1.2 (6)
C11—C12—C13—C14	0.1 (6)	C50—C49—C54—C55	−178.7 (3)
C11—C12—C13—C24	−179.7 (3)	C53—C54—C55—N9	−172.2 (3)
C12—C13—C14—C15	−1.3 (5)	C49—C54—C55—N9	7.7 (5)
C24—C13—C14—C15	178.5 (3)	C53—C54—C55—C56	8.4 (5)
C13—C14—C15—C10	0.7 (5)	C49—C54—C55—C56	−171.8 (3)
C11—C10—C15—C14	1.1 (5)	N9—C55—C56—C57	−0.6 (5)
C9—C10—C15—C14	−176.4 (3)	C54—C55—C56—C57	178.8 (3)
C8—C9—C16—C17	0.6 (5)	C55—C56—C57—C64	−0.9 (5)
C10—C9—C16—C17	179.2 (3)	C55—C56—C57—C58	177.8 (3)
C9—C16—C17—N1	−2.8 (5)	C56—C57—C58—C59	27.8 (5)
C9—C16—C17—C18	177.1 (3)	C64—C57—C58—C59	−153.5 (3)
N1—C17—C18—C19	156.6 (3)	C56—C57—C58—C63	−151.9 (3)
C16—C17—C18—C19	−23.3 (5)	C64—C57—C58—C63	26.8 (5)
N1—C17—C18—C23	−22.5 (5)	C63—C58—C59—C60	−0.8 (5)
C16—C17—C18—C23	157.6 (3)	C57—C58—C59—C60	179.6 (3)
C23—C18—C19—C20	−1.3 (5)	C58—C59—C60—C61	0.4 (5)
C17—C18—C19—C20	179.6 (3)	C59—C60—C61—C62	−0.2 (5)
C18—C19—C20—C21	0.3 (6)	C59—C60—C61—C72	178.9 (4)
C19—C20—C21—C22	1.0 (6)	C60—C61—C62—C63	0.3 (6)
C20—C21—C22—C23	−1.3 (6)	C72—C61—C62—C63	−178.8 (4)
C21—C22—C23—C18	0.3 (6)	C61—C62—C63—C58	−0.7 (6)
C19—C18—C23—C22	1.1 (5)	C59—C58—C63—C62	0.9 (5)
C17—C18—C23—C22	−179.9 (3)	C57—C58—C63—C62	−179.4 (3)
C12—C13—C24—N2	−82.9 (5)	C56—C57—C64—C65	1.0 (5)
C14—C13—C24—N2	97.3 (4)	C58—C57—C64—C65	−177.7 (3)
C30—C25—C26—C27	0.6 (7)	C57—C64—C65—N9	0.4 (5)
C25—C26—C27—C28	−1.0 (6)	C57—C64—C65—C66	−179.0 (3)
C26—C27—C28—C29	0.8 (7)	N9—C65—C66—C71	21.7 (5)
C27—C28—C29—C30	0.0 (7)	C64—C65—C66—C71	−158.8 (4)
C28—C29—C30—C25	−0.4 (6)	N9—C65—C66—C67	−157.6 (3)
C28—C29—C30—C31	−179.0 (4)	C64—C65—C66—C67	21.9 (5)
C26—C25—C30—C29	0.1 (6)	C71—C66—C67—C68	−1.1 (5)
C26—C25—C30—C31	178.7 (4)	C65—C66—C67—C68	178.3 (3)
C29—C30—C31—N5	−176.4 (3)	C66—C67—C68—C69	1.0 (6)
C25—C30—C31—N5	5.1 (5)	C67—C68—C69—C70	−0.1 (6)
C29—C30—C31—C32	4.5 (5)	C68—C69—C70—C71	−0.7 (7)
C25—C30—C31—C32	−174.0 (4)	C69—C70—C71—C66	0.6 (6)
N5—C31—C32—C33	−1.8 (5)	C67—C66—C71—C70	0.3 (6)
C30—C31—C32—C33	177.2 (3)	C65—C66—C71—C70	−179.1 (3)
C31—C32—C33—C40	−0.1 (5)	C60—C61—C72—N10	−88.1 (5)
C31—C32—C33—C34	−179.8 (3)	C62—C61—C72—N10	91.0 (5)
C40—C33—C34—C39	24.7 (5)	C16—C17—N1—C7	2.2 (5)
C32—C33—C34—C39	−155.7 (3)	C18—C17—N1—C7	−177.8 (3)
C40—C33—C34—C35	−157.2 (3)	C8—C7—N1—C17	0.6 (5)
C32—C33—C34—C35	22.5 (5)	C6—C7—N1—C17	−177.7 (3)
C39—C34—C35—C36	−0.8 (5)	C13—C24—N2—N3	47.0 (5)
C33—C34—C35—C36	−179.1 (3)	C32—C31—N5—C41	2.0 (5)
C34—C35—C36—C37	0.2 (5)	C30—C31—N5—C41	−177.1 (3)
C35—C36—C37—C38	1.0 (5)	C40—C41—N5—C31	−0.3 (5)
C35—C36—C37—C48	−175.7 (3)	C42—C41—N5—C31	179.1 (3)
C36—C37—C38—C39	−1.7 (5)	C37—C48—N6—N7	65.5 (4)
C48—C37—C38—C39	175.0 (3)	C64—C65—N9—C55	−2.0 (5)
C37—C38—C39—C34	1.1 (5)	C66—C65—N9—C55	177.5 (3)
C35—C34—C39—C38	0.1 (5)	C56—C55—N9—C65	2.1 (5)
C33—C34—C39—C38	178.4 (3)	C54—C55—N9—C65	−177.4 (3)
C32—C33—C40—C41	1.7 (5)	C61—C72—N10—N11	57.3 (5)
C34—C33—C40—C41	−178.6 (3)

Hydrogen-bond geometry (Å, º) top

Cg4, Cg7, Cg8 and Cg11 are the centroids of the C18–C23, C34–C39, C42–C47 and C58–C63 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···Cg8ⁱ	0.93	2.92	3.601 (4)	132
C21—H21···Cg7ⁱⁱ	0.93	2.78	3.668 (4)	161
C24—H24B···Cg11ⁱⁱⁱ	0.93	2.84	3.443 (5)	121
C36—H36···Cg4	0.93	2.82	3.601 (4)	142

Symmetry codes: (i) x, y, z+1; (ii) x, −y, z+1/2; (iii) x−1, y, z.

Funding information

This work was supported by the Undergraduate Research Training Program of Anhui University (award No. KYXL2017022) and the National Natural Science Foundation of China (award No. 51432001).

References

Ai, Y. Y., Li, Y. G., Ma, H. Q., Su, C. Y. & Yam, V. W. W. (2016). Inorg. Chem. 55, 11920–11929. Web of Science CSD CrossRef CAS PubMed Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fernandez-Cestau, F., Bertrand, B., Pintus, A. & Bochmann, M. (2017). Organometallics, 36, 3304–3312. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 4| April 2019| x190295

https://doi.org/10.1107/S2414314619002955

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-[4-(Azido­meth­yl)phen­yl]-2,6-di­phenyl­pyridine

Structure description

Synthesis and crystallization

Refinement

Structural data

Funding information

References

organic compounds

4-[4-(Azidomethyl)phenyl]-2,6-diphenylpyridine