1,3-Bis(2-ethoxy-phen-yl)triazene methanol 0.33-solvate.

There are three independent mol-ecules of 1,3-bis-(2-ethoxy-phen-yl)triazene and a mol-ecule of methanol in the asymmetric unit of the title compound, C(16)H(19)N(3)O(2)·0.33CH(3)OH. Two mol-ecules related by a non-crystallographic pseudo-twofold rotation axis are linked via distinct inter-molecular N-H⋯N hydrogen bonds, leading to the formation of a dimer with an R(2) (2)(8) graph set. The third mol-ecule is connected to the methanol mol-ecule by O-H⋯N and N-H⋯O hydrogen bonds. There are a number of weak C-H⋯π inter-actions, with H⋯π distances ranging from 2.74 to 2.89 Å between the C-H groups and the aromatic benzene rings.

Related literature

For related structures, see: Rofouei et al. (2009 ▶); Melardi et al.(2008 ▶); Rofouei et al. (2006 ▶). For the structural properties and metal complexes of aryl triazenes, see: Meldola et al. (1888 ▶); Leman et al. (1993 ▶); Chen et al. (2002 ▶); Vrieze et al. (1987 ▶); Hematyar et al. (2008 ▶); Payehghadr et al. (2007 ▶). For hydrogen-bond patterns and graph sets, see: Grell et al. (2002 ▶).

Experimental

Crystal data

C16H19N3O2·0.33CH4O

M = 296.02

Triclinic,

a = 12.146 (3) Å

b = 13.640 (3) Å

c = 16.117 (4) Å

α = 71.448 (5)°

β = 72.827 (4)°

γ = 81.151 (4)°

V = 2413.2 (10) Å3

Z = 6

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.978, T max = 0.992

21014 measured reflections

9421 independent reflections

4997 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.204

S = 1.00

9421 reflections

587 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; 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 datablocks I, global. DOI: 10.1107/S1600536809035338/pv2190sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035338/pv2190Isup2.hkl

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

C16H19N3O2·0.33CH4O	Z = 6
Mr = 296.02	F(000) = 948
Triclinic, P1	Dx = 1.222 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.146 (3) Å	Cell parameters from 2921 reflections
b = 13.640 (3) Å	θ = 2.4–24.6°
c = 16.117 (4) Å	µ = 0.08 mm−1
α = 71.448 (5)°	T = 120 K
β = 72.827 (4)°	Prism, orange
γ = 81.151 (4)°	0.30 × 0.20 × 0.10 mm
V = 2413.2 (10) Å3

Bruker SMART 1000 CCD area-detector diffractometer	9421 independent reflections
Radiation source: fine-focus sealed tube	4997 reflections with I > 2σ(I)
graphite	Rint = 0.048
φ and ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −14→14
Tmin = 0.978, Tmax = 0.992	k = −16→16
21014 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)] = 0.060	Hydrogen site location: difference Fourier map
wR(F2) = 0.204	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.07P)2 + 2P] where P = (Fo2 + 2Fc2)/3
9421 reflections	(Δ/σ)max < 0.001
587 parameters	Δρmax = 0.31 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
O1	0.31967 (13)	0.24889 (12)	0.40953 (10)	0.0360 (4)
O2	0.00977 (12)	0.23580 (12)	0.82111 (10)	0.0334 (4)
N1	0.12742 (15)	0.19444 (14)	0.53596 (12)	0.0312 (5)
N2	0.03282 (15)	0.16622 (14)	0.59722 (12)	0.0289 (5)
N3	0.02050 (15)	0.19607 (14)	0.66913 (12)	0.0314 (5)
H3N	0.0725	0.2323	0.6722	0.038*
C1	0.14480 (18)	0.16900 (16)	0.45427 (14)	0.0272 (5)
C2	0.24629 (18)	0.20179 (16)	0.38631 (15)	0.0296 (6)
C3	0.26635 (19)	0.18578 (17)	0.30162 (15)	0.0322 (6)
H3A	0.3335	0.2099	0.2549	0.039*
C4	0.18748 (19)	0.13438 (17)	0.28613 (15)	0.0344 (6)
H4A	0.2017	0.1224	0.2288	0.041*
C5	0.08808 (19)	0.10025 (18)	0.35339 (15)	0.0342 (6)
H5A	0.0349	0.0646	0.3425	0.041*
C6	0.06734 (18)	0.11877 (17)	0.43658 (15)	0.0303 (6)
H6A	−0.0013	0.0966	0.4823	0.036*
C7	0.41398 (19)	0.29920 (19)	0.33826 (16)	0.0372 (6)
H7A	0.3845	0.3525	0.2903	0.045*
H7B	0.4660	0.2480	0.3107	0.045*
C8	0.4776 (2)	0.3482 (2)	0.37950 (18)	0.0545 (8)
H8A	0.5427	0.3833	0.3325	0.082*
H8B	0.5065	0.2947	0.4267	0.082*
H8C	0.4253	0.3988	0.4064	0.082*
C9	−0.07846 (17)	0.16844 (16)	0.74147 (14)	0.0265 (5)
C10	−0.08259 (18)	0.18916 (16)	0.82198 (14)	0.0277 (5)
C11	−0.17676 (19)	0.15921 (17)	0.89794 (15)	0.0322 (6)
H11A	−0.1797	0.1719	0.9532	0.039*
C12	−0.26562 (18)	0.11094 (17)	0.89177 (15)	0.0330 (6)
H12A	−0.3296	0.0909	0.9430	0.040*
C13	−0.26151 (18)	0.09184 (17)	0.81164 (15)	0.0322 (6)
H13A	−0.3226	0.0588	0.8080	0.039*
C14	−0.16852 (18)	0.12082 (17)	0.73660 (15)	0.0308 (6)
H14A	−0.1664	0.1080	0.6815	0.037*
C15	0.0103 (2)	0.25548 (18)	0.90324 (15)	0.0354 (6)
H15A	0.0089	0.1895	0.9524	0.043*
H15B	−0.0586	0.3004	0.9223	0.043*
C16	0.1185 (2)	0.3083 (2)	0.88496 (17)	0.0480 (7)
H16A	0.1210	0.3227	0.9402	0.072*
H16B	0.1189	0.3735	0.8364	0.072*
H16C	0.1861	0.2631	0.8664	0.072*
O3	−0.03481 (12)	0.44284 (12)	0.63303 (11)	0.0377 (4)
O4	0.33503 (12)	0.04227 (11)	0.62005 (11)	0.0346 (4)
N4	0.17838 (15)	0.36547 (13)	0.63042 (12)	0.0297 (5)
N5	0.28253 (15)	0.32739 (13)	0.63278 (12)	0.0286 (5)
N6	0.30570 (15)	0.23841 (13)	0.61518 (12)	0.0306 (5)
H6N	0.2531	0.2095	0.6047	0.037*
C17	0.14665 (18)	0.46114 (16)	0.64961 (14)	0.0282 (5)
C18	0.03205 (18)	0.50163 (17)	0.65099 (15)	0.0309 (6)
C19	−0.0048 (2)	0.59563 (18)	0.66942 (16)	0.0387 (7)
H19A	−0.0815	0.6237	0.6697	0.046*
C20	0.0692 (2)	0.64865 (18)	0.68742 (18)	0.0435 (7)
H20A	0.0426	0.7124	0.7011	0.052*
C21	0.1819 (2)	0.60992 (18)	0.68580 (17)	0.0424 (7)
H21A	0.2324	0.6470	0.6980	0.051*
C22	0.2204 (2)	0.51652 (17)	0.66619 (15)	0.0334 (6)
H22A	0.2980	0.4903	0.6641	0.040*
C23	−0.13987 (19)	0.4905 (2)	0.60961 (16)	0.0402 (7)
H23A	−0.1235	0.5531	0.5569	0.048*
H23B	−0.1946	0.5113	0.6613	0.048*
C24	−0.1903 (2)	0.4117 (2)	0.58680 (17)	0.0464 (7)
H24A	−0.2624	0.4414	0.5704	0.070*
H24B	−0.2061	0.3503	0.6395	0.070*
H24C	−0.1354	0.3919	0.5356	0.070*
C25	0.41736 (17)	0.18971 (16)	0.61329 (14)	0.0264 (5)
C26	0.43230 (18)	0.08528 (16)	0.61546 (14)	0.0278 (5)
C27	0.54021 (19)	0.03263 (18)	0.61434 (15)	0.0329 (6)
H27A	0.5504	−0.0386	0.6169	0.039*
C28	0.63264 (19)	0.08407 (18)	0.60955 (15)	0.0344 (6)
H28A	0.7062	0.0479	0.6082	0.041*
C29	0.61904 (19)	0.18722 (18)	0.60672 (15)	0.0349 (6)
H29A	0.6829	0.2220	0.6034	0.042*
C30	0.51106 (18)	0.24000 (17)	0.60880 (14)	0.0310 (6)
H30A	0.5014	0.3110	0.6071	0.037*
C31	0.34302 (19)	−0.06530 (16)	0.62645 (15)	0.0316 (6)
H31A	0.3618	−0.1077	0.6836	0.038*
H31B	0.4043	−0.0800	0.5749	0.038*
C32	0.2277 (2)	−0.09031 (18)	0.62455 (17)	0.0388 (6)
H32A	0.2299	−0.1638	0.6288	0.058*
H32B	0.2101	−0.0479	0.5677	0.058*
H32C	0.1678	−0.0755	0.6759	0.058*
O5	0.70638 (12)	0.06592 (11)	0.13410 (10)	0.0317 (4)
O6	0.36080 (12)	0.48301 (12)	0.11751 (11)	0.0362 (4)
N7	0.68644 (15)	0.26576 (14)	0.11614 (12)	0.0294 (5)
N8	0.67007 (15)	0.35282 (14)	0.13324 (12)	0.0293 (5)
N9	0.57197 (15)	0.40407 (13)	0.11906 (12)	0.0307 (5)
H9N	0.5298	0.3809	0.0942	0.037*
C33	0.79371 (18)	0.21153 (16)	0.12693 (14)	0.0259 (5)
C34	0.80398 (18)	0.10554 (16)	0.13416 (14)	0.0277 (5)
C35	0.90725 (19)	0.04810 (17)	0.14109 (15)	0.0318 (6)
H35A	0.9146	−0.0236	0.1455	0.038*
C36	1.00003 (19)	0.09627 (18)	0.14159 (15)	0.0348 (6)
H36A	1.0708	0.0569	0.1462	0.042*
C37	0.99072 (19)	0.20022 (18)	0.13548 (15)	0.0333 (6)
H37A	1.0546	0.2321	0.1361	0.040*
C38	0.88745 (18)	0.25806 (17)	0.12842 (14)	0.0304 (6)
H38A	0.8806	0.3296	0.1246	0.036*
C39	0.7134 (2)	−0.04229 (17)	0.14138 (16)	0.0354 (6)
H39A	0.7355	−0.0844	0.1973	0.043*
H39B	0.7717	−0.0573	0.0885	0.043*
C40	0.5947 (2)	−0.06709 (19)	0.14433 (17)	0.0426 (7)
H40A	0.5955	−0.1407	0.1493	0.064*
H40B	0.5740	−0.0249	0.0887	0.064*
H40C	0.5380	−0.0518	0.1969	0.064*
C41	0.53667 (18)	0.49534 (16)	0.14432 (14)	0.0282 (5)
C42	0.42322 (18)	0.53686 (16)	0.14433 (15)	0.0297 (6)
C43	0.3816 (2)	0.62422 (17)	0.17383 (16)	0.0364 (6)
H43A	0.3051	0.6526	0.1740	0.044*
C44	0.4523 (2)	0.67014 (17)	0.20317 (16)	0.0349 (6)
H44A	0.4235	0.7292	0.2242	0.042*
C45	0.56442 (19)	0.62991 (17)	0.20172 (15)	0.0336 (6)
H45A	0.6123	0.6614	0.2217	0.040*
C46	0.60702 (19)	0.54372 (16)	0.17116 (15)	0.0311 (6)
H46A	0.6848	0.5177	0.1686	0.037*
C47	0.24610 (19)	0.52416 (19)	0.11158 (17)	0.0386 (7)
H47A	0.2488	0.5938	0.0671	0.046*
H47B	0.1978	0.5302	0.1713	0.046*
C48	0.1965 (2)	0.4504 (2)	0.08185 (18)	0.0491 (7)
H48A	0.1181	0.4761	0.0771	0.074*
H48B	0.1943	0.3818	0.1265	0.074*
H48C	0.2450	0.4452	0.0227	0.074*
O7	0.46759 (14)	0.23487 (14)	0.10190 (12)	0.0507 (5)
H7O	0.5406	0.2123	0.0967	0.061*
C49	0.4211 (2)	0.2023 (2)	0.04551 (18)	0.0534 (8)
H49A	0.4724	0.2190	−0.0161	0.080*
H49B	0.3448	0.2379	0.0443	0.080*
H49C	0.4137	0.1273	0.0690	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0283 (8)	0.0449 (9)	0.0346 (8)	−0.0153 (7)	−0.0055 (7)	−0.0076 (7)
O2	0.0295 (8)	0.0445 (8)	0.0306 (7)	−0.0119 (7)	−0.0058 (6)	−0.0146 (6)
N1	0.0236 (9)	0.0422 (10)	0.0281 (9)	−0.0098 (8)	−0.0026 (7)	−0.0110 (8)
N2	0.0233 (9)	0.0320 (9)	0.0301 (9)	−0.0036 (8)	−0.0045 (7)	−0.0087 (8)
N3	0.0280 (9)	0.0401 (10)	0.0298 (9)	−0.0109 (8)	−0.0044 (7)	−0.0141 (8)
C1	0.0267 (10)	0.0265 (11)	0.0284 (10)	−0.0023 (9)	−0.0084 (9)	−0.0067 (9)
C2	0.0279 (11)	0.0273 (11)	0.0333 (11)	−0.0019 (9)	−0.0107 (9)	−0.0061 (9)
C3	0.0244 (11)	0.0377 (12)	0.0319 (11)	0.0000 (10)	−0.0070 (9)	−0.0079 (10)
C4	0.0347 (12)	0.0389 (12)	0.0346 (11)	0.0042 (10)	−0.0138 (9)	−0.0162 (10)
C5	0.0295 (11)	0.0355 (12)	0.0426 (12)	−0.0009 (10)	−0.0144 (10)	−0.0143 (10)
C6	0.0232 (10)	0.0338 (12)	0.0323 (11)	−0.0041 (9)	−0.0065 (9)	−0.0071 (9)
C7	0.0265 (11)	0.0391 (13)	0.0384 (13)	−0.0083 (10)	−0.0054 (10)	−0.0009 (10)
C8	0.0448 (14)	0.0673 (17)	0.0480 (15)	−0.0342 (13)	−0.0114 (12)	0.0014 (13)
C9	0.0215 (10)	0.0261 (11)	0.0304 (11)	−0.0017 (9)	−0.0076 (9)	−0.0056 (9)
C10	0.0229 (10)	0.0295 (11)	0.0297 (11)	−0.0021 (9)	−0.0068 (9)	−0.0073 (9)
C11	0.0321 (12)	0.0359 (12)	0.0271 (11)	−0.0017 (10)	−0.0067 (9)	−0.0082 (9)
C12	0.0205 (11)	0.0353 (12)	0.0357 (12)	−0.0034 (10)	−0.0016 (9)	−0.0048 (10)
C13	0.0210 (10)	0.0343 (12)	0.0384 (12)	−0.0047 (9)	−0.0077 (9)	−0.0053 (10)
C14	0.0276 (11)	0.0340 (12)	0.0328 (11)	−0.0011 (10)	−0.0111 (9)	−0.0100 (9)
C15	0.0391 (12)	0.0416 (12)	0.0296 (11)	−0.0075 (11)	−0.0096 (10)	−0.0130 (10)
C16	0.0536 (14)	0.0573 (15)	0.0396 (13)	−0.0226 (13)	−0.0123 (11)	−0.0138 (11)
O3	0.0254 (7)	0.0351 (8)	0.0549 (9)	0.0009 (7)	−0.0170 (7)	−0.0115 (7)
O4	0.0244 (7)	0.0296 (8)	0.0565 (9)	−0.0027 (6)	−0.0147 (7)	−0.0174 (7)
N4	0.0237 (9)	0.0265 (9)	0.0413 (10)	0.0005 (8)	−0.0109 (8)	−0.0121 (8)
N5	0.0264 (9)	0.0287 (9)	0.0331 (9)	−0.0029 (8)	−0.0091 (7)	−0.0105 (7)
N6	0.0246 (9)	0.0318 (9)	0.0428 (10)	−0.0024 (8)	−0.0128 (8)	−0.0169 (8)
C17	0.0285 (11)	0.0252 (11)	0.0303 (11)	−0.0015 (9)	−0.0096 (9)	−0.0057 (9)
C18	0.0276 (11)	0.0306 (11)	0.0337 (11)	−0.0051 (10)	−0.0091 (9)	−0.0056 (9)
C19	0.0310 (12)	0.0328 (13)	0.0471 (14)	0.0058 (10)	−0.0101 (10)	−0.0083 (11)
C20	0.0476 (14)	0.0275 (12)	0.0586 (15)	0.0040 (11)	−0.0169 (12)	−0.0173 (11)
C21	0.0454 (14)	0.0318 (12)	0.0563 (14)	−0.0017 (11)	−0.0190 (11)	−0.0167 (11)
C22	0.0309 (11)	0.0267 (11)	0.0450 (12)	−0.0008 (10)	−0.0140 (10)	−0.0103 (10)
C23	0.0271 (11)	0.0489 (15)	0.0403 (13)	−0.0016 (11)	−0.0130 (10)	−0.0036 (11)
C24	0.0311 (12)	0.0602 (16)	0.0468 (14)	−0.0024 (12)	−0.0165 (11)	−0.0086 (12)
C25	0.0202 (10)	0.0325 (11)	0.0276 (10)	−0.0022 (9)	−0.0069 (8)	−0.0095 (9)
C26	0.0255 (10)	0.0300 (11)	0.0315 (11)	−0.0014 (9)	−0.0111 (9)	−0.0105 (9)
C27	0.0314 (11)	0.0322 (12)	0.0385 (12)	0.0021 (10)	−0.0133 (9)	−0.0131 (9)
C28	0.0223 (10)	0.0445 (13)	0.0405 (12)	0.0034 (10)	−0.0130 (9)	−0.0159 (10)
C29	0.0239 (10)	0.0405 (13)	0.0440 (12)	−0.0068 (10)	−0.0135 (9)	−0.0109 (10)
C30	0.0289 (11)	0.0334 (11)	0.0368 (11)	−0.0043 (9)	−0.0128 (9)	−0.0138 (9)
C31	0.0330 (12)	0.0255 (11)	0.0373 (12)	−0.0024 (9)	−0.0071 (10)	−0.0123 (9)
C32	0.0396 (13)	0.0343 (12)	0.0462 (13)	−0.0080 (11)	−0.0119 (11)	−0.0136 (10)
O5	0.0277 (7)	0.0287 (8)	0.0415 (8)	−0.0052 (6)	−0.0109 (6)	−0.0107 (6)
O6	0.0265 (7)	0.0356 (8)	0.0526 (9)	−0.0013 (7)	−0.0171 (7)	−0.0152 (7)
N7	0.0251 (9)	0.0313 (9)	0.0330 (9)	−0.0027 (8)	−0.0065 (7)	−0.0116 (8)
N8	0.0263 (9)	0.0283 (9)	0.0324 (9)	−0.0016 (8)	−0.0075 (8)	−0.0078 (8)
N9	0.0238 (9)	0.0305 (10)	0.0391 (10)	0.0006 (8)	−0.0112 (8)	−0.0104 (8)
C33	0.0245 (10)	0.0299 (11)	0.0261 (10)	−0.0031 (9)	−0.0079 (8)	−0.0100 (8)
C34	0.0266 (11)	0.0287 (11)	0.0285 (10)	−0.0048 (9)	−0.0078 (9)	−0.0072 (9)
C35	0.0316 (11)	0.0284 (11)	0.0378 (11)	−0.0005 (10)	−0.0110 (9)	−0.0121 (9)
C36	0.0287 (11)	0.0391 (13)	0.0365 (12)	0.0021 (10)	−0.0144 (10)	−0.0076 (10)
C37	0.0262 (11)	0.0395 (13)	0.0367 (12)	−0.0067 (10)	−0.0104 (9)	−0.0101 (10)
C38	0.0301 (11)	0.0313 (11)	0.0323 (11)	−0.0039 (10)	−0.0096 (9)	−0.0105 (9)
C39	0.0400 (12)	0.0249 (11)	0.0419 (12)	−0.0087 (10)	−0.0118 (10)	−0.0062 (10)
C40	0.0463 (14)	0.0379 (13)	0.0453 (13)	−0.0162 (11)	−0.0119 (11)	−0.0081 (11)
C41	0.0272 (11)	0.0253 (11)	0.0295 (11)	−0.0038 (9)	−0.0065 (9)	−0.0044 (9)
C42	0.0275 (11)	0.0266 (11)	0.0334 (11)	−0.0026 (9)	−0.0103 (9)	−0.0039 (9)
C43	0.0289 (12)	0.0308 (12)	0.0464 (13)	0.0012 (10)	−0.0090 (10)	−0.0094 (10)
C44	0.0353 (12)	0.0250 (11)	0.0429 (13)	−0.0004 (10)	−0.0087 (10)	−0.0100 (10)
C45	0.0324 (12)	0.0269 (11)	0.0424 (12)	−0.0043 (10)	−0.0116 (10)	−0.0084 (10)
C46	0.0266 (11)	0.0276 (11)	0.0380 (12)	−0.0018 (9)	−0.0088 (9)	−0.0077 (9)
C47	0.0249 (11)	0.0469 (14)	0.0429 (13)	0.0008 (11)	−0.0116 (10)	−0.0106 (11)
C48	0.0328 (12)	0.0644 (17)	0.0580 (15)	−0.0062 (12)	−0.0187 (11)	−0.0210 (13)
O7	0.0327 (9)	0.0655 (11)	0.0647 (10)	−0.0042 (8)	−0.0145 (8)	−0.0315 (9)
C49	0.0505 (15)	0.0630 (17)	0.0545 (15)	−0.0103 (14)	−0.0170 (13)	−0.0214 (13)

O1—C2	1.369 (3)	C24—H24B	0.9800
O1—C7	1.437 (3)	C24—H24C	0.9800
O2—C10	1.367 (3)	C25—C30	1.390 (3)
O2—C15	1.434 (3)	C25—C26	1.398 (3)
N1—N2	1.291 (2)	C26—C27	1.392 (3)
N1—C1	1.415 (3)	C27—C28	1.384 (3)
N2—N3	1.308 (3)	C27—H27A	0.9500
N3—C9	1.407 (3)	C28—C29	1.379 (3)
N3—H3N	0.8800	C28—H28A	0.9500
C1—C6	1.385 (3)	C29—C30	1.392 (3)
C1—C2	1.407 (3)	C29—H29A	0.9500
C2—C3	1.395 (3)	C30—H30A	0.9500
C3—C4	1.390 (3)	C31—C32	1.503 (3)
C3—H3A	0.9500	C31—H31A	0.9900
C4—C5	1.389 (3)	C31—H31B	0.9900
C4—H4A	0.9500	C32—H32A	0.9800
C5—C6	1.386 (3)	C32—H32B	0.9800
C5—H5A	0.9500	C32—H32C	0.9800
C6—H6A	0.9500	O5—C34	1.377 (3)
C7—C8	1.494 (4)	O5—C39	1.434 (3)
C7—H7A	0.9900	O6—C42	1.367 (3)
C7—H7B	0.9900	O6—C47	1.438 (3)
C8—H8A	0.9800	N7—N8	1.276 (3)
C8—H8B	0.9800	N7—C33	1.425 (3)
C8—H8C	0.9800	N8—N9	1.328 (2)
C9—C14	1.388 (3)	N9—C41	1.398 (3)
C9—C10	1.399 (3)	N9—H9N	0.8800
C10—C11	1.404 (3)	C33—C38	1.396 (3)
C11—C12	1.390 (3)	C33—C34	1.402 (3)
C11—H11A	0.9500	C34—C35	1.387 (3)
C12—C13	1.382 (3)	C35—C36	1.392 (3)
C12—H12A	0.9500	C35—H35A	0.9500
C13—C14	1.386 (3)	C36—C37	1.379 (3)
C13—H13A	0.9500	C36—H36A	0.9500
C14—H14A	0.9500	C37—C38	1.390 (3)
C15—C16	1.503 (3)	C37—H37A	0.9500
C15—H15A	0.9900	C38—H38A	0.9500
C15—H15B	0.9900	C39—C40	1.514 (3)
C16—H16A	0.9800	C39—H39A	0.9900
C16—H16B	0.9800	C39—H39B	0.9900
C16—H16C	0.9800	C40—H40A	0.9800
O3—C18	1.369 (3)	C40—H40B	0.9800
O3—C23	1.438 (3)	C40—H40C	0.9800
O4—C26	1.371 (3)	C41—C46	1.388 (3)
O4—C31	1.428 (3)	C41—C42	1.407 (3)
N4—N5	1.298 (2)	C42—C43	1.391 (3)
N4—C17	1.407 (3)	C43—C44	1.396 (4)
N5—N6	1.304 (3)	C43—H43A	0.9500
N6—C25	1.412 (3)	C44—C45	1.384 (3)
N6—H6N	0.8800	C44—H44A	0.9500
C17—C22	1.387 (3)	C45—C46	1.387 (3)
C17—C18	1.413 (3)	C45—H45A	0.9500
C18—C19	1.386 (3)	C46—H46A	0.9500
C19—C20	1.380 (4)	C47—C48	1.506 (4)
C19—H19A	0.9500	C47—H47A	0.9900
C20—C21	1.385 (4)	C47—H47B	0.9900
C20—H20A	0.9500	C48—H48A	0.9800
C21—C22	1.388 (3)	C48—H48B	0.9800
C21—H21A	0.9500	C48—H48C	0.9800
C22—H22A	0.9500	O7—C49	1.407 (3)
C23—C24	1.501 (4)	O7—H7O	0.8807
C23—H23A	0.9900	C49—H49A	0.9800
C23—H23B	0.9900	C49—H49B	0.9800
C24—H24A	0.9800	C49—H49C	0.9800
C2—O1—C7	117.58 (18)	C30—C25—C26	119.43 (19)
C10—O2—C15	117.73 (16)	C30—C25—N6	123.6 (2)
N2—N1—C1	115.95 (19)	C26—C25—N6	116.94 (19)
N1—N2—N3	112.46 (18)	O4—C26—C27	125.0 (2)
N2—N3—C9	117.88 (19)	O4—C26—C25	115.26 (18)
N2—N3—H3N	121.1	C27—C26—C25	119.7 (2)
C9—N3—H3N	121.1	C28—C27—C26	120.0 (2)
C6—C1—C2	119.2 (2)	C28—C27—H27A	120.0
C6—C1—N1	124.47 (18)	C26—C27—H27A	120.0
C2—C1—N1	116.3 (2)	C29—C28—C27	120.7 (2)
O1—C2—C3	124.33 (19)	C29—C28—H28A	119.7
O1—C2—C1	115.8 (2)	C27—C28—H28A	119.7
C3—C2—C1	119.9 (2)	C28—C29—C30	119.5 (2)
C4—C3—C2	119.6 (2)	C28—C29—H29A	120.2
C4—C3—H3A	120.2	C30—C29—H29A	120.2
C2—C3—H3A	120.2	C25—C30—C29	120.6 (2)
C5—C4—C3	120.8 (2)	C25—C30—H30A	119.7
C5—C4—H4A	119.6	C29—C30—H30A	119.7
C3—C4—H4A	119.6	O4—C31—C32	107.13 (18)
C6—C5—C4	119.3 (2)	O4—C31—H31A	110.3
C6—C5—H5A	120.4	C32—C31—H31A	110.3
C4—C5—H5A	120.4	O4—C31—H31B	110.3
C1—C6—C5	121.2 (2)	C32—C31—H31B	110.3
C1—C6—H6A	119.4	H31A—C31—H31B	108.5
C5—C6—H6A	119.4	C31—C32—H32A	109.5
O1—C7—C8	107.4 (2)	C31—C32—H32B	109.5
O1—C7—H7A	110.2	H32A—C32—H32B	109.5
C8—C7—H7A	110.2	C31—C32—H32C	109.5
O1—C7—H7B	110.2	H32A—C32—H32C	109.5
C8—C7—H7B	110.2	H32B—C32—H32C	109.5
H7A—C7—H7B	108.5	C34—O5—C39	117.07 (16)
C7—C8—H8A	109.5	C42—O6—C47	117.96 (18)
C7—C8—H8B	109.5	N8—N7—C33	113.74 (18)
H8A—C8—H8B	109.5	N7—N8—N9	112.79 (19)
C7—C8—H8C	109.5	N8—N9—C41	118.98 (19)
H8A—C8—H8C	109.5	N8—N9—H9N	120.5
H8B—C8—H8C	109.5	C41—N9—H9N	120.5
C14—C9—C10	119.84 (19)	C38—C33—C34	119.4 (2)
C14—C9—N3	123.3 (2)	C38—C33—N7	124.04 (19)
C10—C9—N3	116.9 (2)	C34—C33—N7	116.52 (19)
O2—C10—C9	116.08 (17)	O5—C34—C35	124.6 (2)
O2—C10—C11	124.3 (2)	O5—C34—C33	115.34 (18)
C9—C10—C11	119.6 (2)	C35—C34—C33	120.1 (2)
C12—C11—C10	119.6 (2)	C34—C35—C36	119.5 (2)
C12—C11—H11A	120.2	C34—C35—H35A	120.2
C10—C11—H11A	120.2	C36—C35—H35A	120.2
C13—C12—C11	120.4 (2)	C37—C36—C35	121.0 (2)
C13—C12—H12A	119.8	C37—C36—H36A	119.5
C11—C12—H12A	119.8	C35—C36—H36A	119.5
C12—C13—C14	120.2 (2)	C36—C37—C38	119.7 (2)
C12—C13—H13A	119.9	C36—C37—H37A	120.2
C14—C13—H13A	119.9	C38—C37—H37A	120.2
C13—C14—C9	120.4 (2)	C37—C38—C33	120.3 (2)
C13—C14—H14A	119.8	C37—C38—H38A	119.8
C9—C14—H14A	119.8	C33—C38—H38A	119.8
O2—C15—C16	107.77 (18)	O5—C39—C40	106.65 (18)
O2—C15—H15A	110.2	O5—C39—H39A	110.4
C16—C15—H15A	110.2	C40—C39—H39A	110.4
O2—C15—H15B	110.2	O5—C39—H39B	110.4
C16—C15—H15B	110.2	C40—C39—H39B	110.4
H15A—C15—H15B	108.5	H39A—C39—H39B	108.6
C15—C16—H16A	109.5	C39—C40—H40A	109.5
C15—C16—H16B	109.5	C39—C40—H40B	109.5
H16A—C16—H16B	109.5	H40A—C40—H40B	109.5
C15—C16—H16C	109.5	C39—C40—H40C	109.5
H16A—C16—H16C	109.5	H40A—C40—H40C	109.5
H16B—C16—H16C	109.5	H40B—C40—H40C	109.5
C18—O3—C23	118.40 (18)	C46—C41—N9	123.0 (2)
C26—O4—C31	118.17 (16)	C46—C41—C42	119.7 (2)
N5—N4—C17	115.73 (19)	N9—C41—C42	117.3 (2)
N4—N5—N6	112.45 (18)	O6—C42—C43	125.2 (2)
N5—N6—C25	118.21 (19)	O6—C42—C41	115.1 (2)
N5—N6—H6N	120.9	C43—C42—C41	119.6 (2)
C25—N6—H6N	120.9	C42—C43—C44	120.0 (2)
C22—C17—N4	124.1 (2)	C42—C43—H43A	120.0
C22—C17—C18	119.4 (2)	C44—C43—H43A	120.0
N4—C17—C18	116.5 (2)	C45—C44—C43	120.2 (2)
O3—C18—C19	124.8 (2)	C45—C44—H44A	119.9
O3—C18—C17	115.8 (2)	C43—C44—H44A	119.9
C19—C18—C17	119.4 (2)	C44—C45—C46	120.2 (2)
C20—C19—C18	120.3 (2)	C44—C45—H45A	119.9
C20—C19—H19A	119.8	C46—C45—H45A	119.9
C18—C19—H19A	119.8	C45—C46—C41	120.3 (2)
C19—C20—C21	120.7 (2)	C45—C46—H46A	119.8
C19—C20—H20A	119.6	C41—C46—H46A	119.8
C21—C20—H20A	119.6	O6—C47—C48	107.2 (2)
C20—C21—C22	119.6 (2)	O6—C47—H47A	110.3
C20—C21—H21A	120.2	C48—C47—H47A	110.3
C22—C21—H21A	120.2	O6—C47—H47B	110.3
C17—C22—C21	120.6 (2)	C48—C47—H47B	110.3
C17—C22—H22A	119.7	H47A—C47—H47B	108.5
C21—C22—H22A	119.7	C47—C48—H48A	109.5
O3—C23—C24	107.0 (2)	C47—C48—H48B	109.5
O3—C23—H23A	110.3	H48A—C48—H48B	109.5
C24—C23—H23A	110.3	C47—C48—H48C	109.5
O3—C23—H23B	110.3	H48A—C48—H48C	109.5
C24—C23—H23B	110.3	H48B—C48—H48C	109.5
H23A—C23—H23B	108.6	C49—O7—H7O	111.0
C23—C24—H24A	109.5	O7—C49—H49A	109.5
C23—C24—H24B	109.5	O7—C49—H49B	109.5
H24A—C24—H24B	109.5	H49A—C49—H49B	109.5
C23—C24—H24C	109.5	O7—C49—H49C	109.5
H24A—C24—H24C	109.5	H49A—C49—H49C	109.5
H24B—C24—H24C	109.5	H49B—C49—H49C	109.5
C1—N1—N2—N3	−177.34 (17)	C18—O3—C23—C24	175.79 (18)
N1—N2—N3—C9	−178.95 (17)	N5—N6—C25—C30	−15.0 (3)
N2—N1—C1—C6	1.2 (3)	N5—N6—C25—C26	165.52 (18)
N2—N1—C1—C2	178.45 (18)	C31—O4—C26—C27	1.6 (3)
C7—O1—C2—C3	10.1 (3)	C31—O4—C26—C25	−177.33 (18)
C7—O1—C2—C1	−169.62 (18)	C30—C25—C26—O4	179.89 (19)
C6—C1—C2—O1	−178.68 (19)	N6—C25—C26—O4	−0.6 (3)
N1—C1—C2—O1	3.9 (3)	C30—C25—C26—C27	0.9 (3)
C6—C1—C2—C3	1.6 (3)	N6—C25—C26—C27	−179.60 (19)
N1—C1—C2—C3	−175.85 (19)	O4—C26—C27—C28	180.0 (2)
O1—C2—C3—C4	178.2 (2)	C25—C26—C27—C28	−1.1 (3)
C1—C2—C3—C4	−2.1 (3)	C26—C27—C28—C29	0.6 (3)
C2—C3—C4—C5	1.0 (3)	C27—C28—C29—C30	0.1 (3)
C3—C4—C5—C6	0.6 (3)	C26—C25—C30—C29	−0.2 (3)
C2—C1—C6—C5	0.1 (3)	N6—C25—C30—C29	−179.7 (2)
N1—C1—C6—C5	177.3 (2)	C28—C29—C30—C25	−0.3 (3)
C4—C5—C6—C1	−1.1 (3)	C26—O4—C31—C32	−176.52 (18)
C2—O1—C7—C8	177.48 (19)	C33—N7—N8—N9	177.30 (16)
N2—N3—C9—C14	−6.8 (3)	N7—N8—N9—C41	173.13 (17)
N2—N3—C9—C10	171.86 (18)	N8—N7—C33—C38	−18.7 (3)
C15—O2—C10—C9	−178.17 (18)	N8—N7—C33—C34	162.85 (18)
C15—O2—C10—C11	−0.1 (3)	C39—O5—C34—C35	−0.3 (3)
C14—C9—C10—O2	179.74 (18)	C39—O5—C34—C33	179.99 (18)
N3—C9—C10—O2	1.0 (3)	C38—C33—C34—O5	178.60 (18)
C14—C9—C10—C11	1.5 (3)	N7—C33—C34—O5	−2.9 (3)
N3—C9—C10—C11	−177.20 (19)	C38—C33—C34—C35	−1.1 (3)
O2—C10—C11—C12	−179.1 (2)	N7—C33—C34—C35	177.37 (19)
C9—C10—C11—C12	−1.1 (3)	O5—C34—C35—C36	−179.2 (2)
C10—C11—C12—C13	0.3 (3)	C33—C34—C35—C36	0.5 (3)
C11—C12—C13—C14	0.0 (3)	C34—C35—C36—C37	0.1 (3)
C12—C13—C14—C9	0.5 (3)	C35—C36—C37—C38	−0.2 (3)
C10—C9—C14—C13	−1.3 (3)	C36—C37—C38—C33	−0.4 (3)
N3—C9—C14—C13	177.4 (2)	C34—C33—C38—C37	1.1 (3)
C10—O2—C15—C16	−179.05 (19)	N7—C33—C38—C37	−177.32 (19)
C17—N4—N5—N6	179.42 (16)	C34—O5—C39—C40	177.32 (18)
N4—N5—N6—C25	178.42 (17)	N8—N9—C41—C46	9.9 (3)
N5—N4—C17—C22	3.0 (3)	N8—N9—C41—C42	−168.33 (18)
N5—N4—C17—C18	−177.49 (18)	C47—O6—C42—C43	5.7 (3)
C23—O3—C18—C19	16.0 (3)	C47—O6—C42—C41	−176.92 (18)
C23—O3—C18—C17	−163.72 (18)	C46—C41—C42—O6	−179.48 (18)
C22—C17—C18—O3	179.33 (19)	N9—C41—C42—O6	−1.2 (3)
N4—C17—C18—O3	−0.2 (3)	C46—C41—C42—C43	−1.9 (3)
C22—C17—C18—C19	−0.4 (3)	N9—C41—C42—C43	176.37 (19)
N4—C17—C18—C19	−179.97 (19)	O6—C42—C43—C44	177.3 (2)
O3—C18—C19—C20	179.5 (2)	C41—C42—C43—C44	0.0 (3)
C17—C18—C19—C20	−0.8 (3)	C42—C43—C44—C45	1.0 (3)
C18—C19—C20—C21	1.2 (4)	C43—C44—C45—C46	0.0 (3)
C19—C20—C21—C22	−0.3 (4)	C44—C45—C46—C41	−1.9 (3)
N4—C17—C22—C21	−179.2 (2)	N9—C41—C46—C45	−175.31 (19)
C18—C17—C22—C21	1.3 (3)	C42—C41—C46—C45	2.9 (3)
C20—C21—C22—C17	−1.0 (4)	C42—O6—C47—C48	−179.43 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···N4	0.88	2.20	3.024 (3)	156
N6—H6N···N1	0.88	2.20	3.033 (3)	158
N9—H9N···O7	0.88	2.19	2.920 (3)	140
O7—H7O···N7	0.88	2.15	2.839 (3)	134
C28—H28A···Cg1i	0.95	2.89	3.712 (3)	146
C36—H36A···Cg2i	0.95	2.74	3.549 (3)	144
C15—H15A···Cg3ii	0.99	2.76	3.463 (3)	128
C32—H32C···Cg3i	0.98	2.80	3.593 (3)	138
C40—H40C···Cg4i	0.98	2.84	3.632 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯N4	0.88	2.20	3.024 (3)	156
N6—H6N⋯N1	0.88	2.20	3.033 (3)	158
N9—H9N⋯O7	0.88	2.19	2.920 (3)	140
O7—H7O⋯N7	0.88	2.15	2.839 (3)	134
C28—H28A⋯Cg1i	0.95	2.89	3.712 (3)	146
C36—H36A⋯Cg2i	0.95	2.74	3.549 (3)	144
C15—H15A⋯Cg3ii	0.99	2.76	3.463 (3)	128
C32—H32C⋯Cg3i	0.98	2.80	3.593 (3)	138
C40—H40C⋯Cg4i	0.98	2.84	3.632 (3)	138

Symmetry codes: (i) ; (ii) . Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1–C6, C9–C14, C33–C38 and C25–C30 rings, respectively.