4-(1H-Indol-3-yl)-2,6-bis(4-methoxy­phenyl)­pyridine

Tu, S.; Li, T.; Fang, F.

doi:10.1107/S1600536804030387

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4-(1H-Indol-3-yl)-2,6-bis(4-methoxyphenyl)pyridine

S. Tu, T. Li and F. Fang

The title compound, C₂₇H₂₂N₂O₂, was synthesized by the reaction of indole-3-carbaldehyde with 4-methoxyacetophenone and ammonium acetate in glycol under microwave irradiation. X-ray analysis reveals that N—H

N hydrogen bonds link the molecules into zigzag chains along [01 $\overline1$ ].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804030387/ci6488sup1.cif Contains datablocks y031221, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804030387/ci6488Isup2.hkl Contains datablock I

CCDC reference: 259846

checkCIF report

Key indicators

Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.003 Å
R factor = 0.074
wR factor = 0.145
Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.72 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.20 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.62 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2000-2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

4-indol-2,6-bis(4-methoxyphenyl)pyridine top

Crystal data top

C₂₇H₂₂N₂O₂	Z = 4
M_r = 406.47	F(000) = 856
Triclinic, P1	D_x = 1.291 Mg m⁻³
Hall symbol: -P 1	Melting point = 505–506 K
a = 8.7438 (13) Å	Mo Kα radiation, λ = 0.71070 Å
b = 16.341 (2) Å	Cell parameters from 7351 reflections
c = 16.460 (2) Å	θ = 3.1–27.5°
α = 68.442 (11)°	µ = 0.08 mm⁻¹
β = 76.059 (12)°	T = 193 K
γ = 75.827 (12)°	Block, orange
V = 2090.7 (5) Å³	0.51 × 0.42 × 0.20 mm

Data collection top

Rigaku Mercury diffractometer	9420 independent reflections
Radiation source: fine-focus sealed tube	7619 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan (Jacobson, 1998)	k = −21→21
T_min = 0.959, T_max = 0.984	l = −20→21
23621 measured reflections

Refinement top

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ²(F_o²) + (0.0393P)² + 1.3567P] where P = (F_o² + 2F_c²)/3
9420 reflections	(Δ/σ)_max < 0.001
571 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.3276 (2)	0.96180 (12)	0.55733 (10)	0.0452 (4)
O2	0.3169 (2)	1.31433 (12)	1.07570 (14)	0.0542 (5)
O3	0.6521 (2)	0.47286 (12)	0.06268 (11)	0.0490 (5)
O4	−0.1783 (2)	0.82461 (12)	0.56413 (14)	0.0577 (6)
N1	0.2466 (2)	1.01685 (11)	0.93107 (11)	0.0247 (4)
N2	0.1874 (2)	0.66435 (12)	1.27130 (12)	0.0302 (4)
N3	0.2966 (2)	0.52086 (11)	0.43411 (11)	0.0243 (4)
N4	0.3614 (2)	0.16583 (12)	0.77256 (12)	0.0307 (4)
C1	0.2347 (2)	0.94347 (13)	0.91513 (13)	0.0244 (4)
C2	0.1997 (2)	0.86574 (13)	0.98286 (13)	0.0253 (4)
H2	0.1915	0.8158	0.9686	0.030*
C3	0.1765 (2)	0.86027 (13)	1.07113 (13)	0.0243 (4)
C4	0.1865 (2)	0.93687 (13)	1.08700 (13)	0.0255 (4)
H4	0.1682	0.9374	1.1461	0.031*
C5	0.2232 (2)	1.01251 (13)	1.01668 (13)	0.0245 (4)
C6	0.2619 (3)	0.94761 (14)	0.82114 (13)	0.0255 (4)
C7	0.1940 (3)	1.02213 (14)	0.75670 (14)	0.0288 (5)
H7	0.1299	1.0716	0.7729	0.035*
C8	0.2191 (3)	1.02453 (15)	0.66980 (14)	0.0334 (5)
H8	0.1727	1.0757	0.6267	0.040*
C9	0.3115 (3)	0.95285 (16)	0.64491 (14)	0.0339 (5)
C10	0.3802 (3)	0.87839 (16)	0.70747 (15)	0.0385 (6)
H10	0.4441	0.8291	0.6909	0.046*
C11	0.3544 (3)	0.87664 (15)	0.79490 (14)	0.0342 (5)
H11	0.4014	0.8255	0.8377	0.041*
C12	0.1549 (3)	0.77669 (13)	1.14359 (13)	0.0252 (4)
C13	0.2119 (3)	0.74905 (14)	1.22225 (14)	0.0296 (5)
H13	0.2612	0.7842	1.2398	0.036*
C14	0.1146 (2)	0.63371 (13)	1.22543 (13)	0.0256 (4)
C15	0.0665 (3)	0.55180 (14)	1.24905 (15)	0.0311 (5)
H15	0.0887	0.5051	1.3021	0.037*
C16	−0.0144 (3)	0.54116 (15)	1.19241 (16)	0.0349 (5)
H16	−0.0487	0.4859	1.2068	0.042*
C17	−0.0473 (3)	0.60995 (15)	1.11413 (15)	0.0346 (5)
H17	−0.1051	0.6009	1.0770	0.041*
C18	0.0030 (3)	0.69056 (14)	1.09004 (14)	0.0284 (5)
H18	−0.0200	0.7368	1.0369	0.034*
C19	0.0883 (2)	0.70323 (13)	1.14507 (13)	0.0235 (4)
C20	0.2443 (3)	1.09166 (13)	1.03404 (13)	0.0251 (4)
C21	0.1420 (3)	1.12144 (14)	1.09989 (14)	0.0269 (4)
H21	0.0571	1.0904	1.1347	0.032*
C22	0.1610 (3)	1.19599 (15)	1.11628 (15)	0.0321 (5)
H22	0.0890	1.2160	1.1612	0.039*
C23	0.2862 (3)	1.24051 (15)	1.06616 (16)	0.0349 (5)
C24	0.3917 (3)	1.21023 (15)	1.00128 (16)	0.0341 (5)
H24	0.4788	1.2401	0.9680	0.041*
C25	0.3709 (3)	1.13725 (14)	0.98492 (14)	0.0293 (5)
H25	0.4431	1.1176	0.9398	0.035*
C26	0.4272 (4)	0.89136 (19)	0.52816 (17)	0.0514 (7)
H26A	0.5353	0.8826	0.5406	0.077*
H26B	0.4317	0.9069	0.4643	0.077*
H26C	0.3833	0.8361	0.5595	0.077*
C27	0.1971 (4)	1.3594 (2)	1.1274 (2)	0.0641 (9)
H27A	0.0950	1.3726	1.1065	0.096*
H27B	0.2279	1.4153	1.1217	0.096*
H27C	0.1858	1.3213	1.1897	0.096*
H1	0.224 (4)	0.629 (2)	1.325 (2)	0.062 (9)*
C28	0.3950 (2)	0.44842 (13)	0.41886 (13)	0.0243 (4)
C29	0.4374 (2)	0.37063 (13)	0.48695 (13)	0.0246 (4)
H29	0.5076	0.3213	0.4733	0.029*
C30	0.3778 (2)	0.36445 (13)	0.57523 (13)	0.0233 (4)
C31	0.2790 (2)	0.44024 (13)	0.59025 (13)	0.0243 (4)
H31	0.2380	0.4401	0.6492	0.029*
C32	0.2400 (2)	0.51600 (13)	0.51953 (13)	0.0229 (4)
C33	0.4586 (2)	0.45403 (14)	0.32494 (13)	0.0252 (4)
C34	0.5109 (3)	0.53120 (14)	0.26280 (14)	0.0286 (5)
H34	0.5038	0.5814	0.2805	0.034*
C35	0.5728 (3)	0.53544 (15)	0.17613 (14)	0.0327 (5)
H35	0.6063	0.5887	0.1345	0.039*
C36	0.5864 (3)	0.46232 (16)	0.14944 (14)	0.0350 (5)
C37	0.5347 (3)	0.38517 (16)	0.21005 (15)	0.0399 (6)
H37	0.5425	0.3350	0.1923	0.048*
C38	0.4715 (3)	0.38201 (15)	0.29691 (14)	0.0334 (5)
H38	0.4361	0.3291	0.3381	0.040*
C39	0.4089 (3)	0.28029 (13)	0.64746 (13)	0.0249 (4)
C40	0.3022 (3)	0.25040 (14)	0.72368 (13)	0.0297 (5)
H40	0.2016	0.2839	0.7399	0.036*
C41	0.5090 (3)	0.13833 (13)	0.72914 (13)	0.0253 (4)
C42	0.6139 (3)	0.05762 (14)	0.75325 (14)	0.0304 (5)
H42	0.5860	0.0099	0.8052	0.037*
C43	0.7589 (3)	0.04970 (15)	0.69911 (15)	0.0338 (5)
H43	0.8327	−0.0047	0.7137	0.041*
C44	0.8004 (3)	0.12014 (15)	0.62276 (15)	0.0331 (5)
H44	0.9029	0.1131	0.5874	0.040*
C45	0.6954 (3)	0.19974 (14)	0.59779 (14)	0.0282 (5)
H45	0.7249	0.2471	0.5459	0.034*
C46	0.5449 (2)	0.20925 (13)	0.65033 (13)	0.0232 (4)
C47	0.1289 (2)	0.59525 (13)	0.53513 (13)	0.0241 (4)
C48	0.1415 (3)	0.62720 (14)	0.60038 (14)	0.0267 (4)
H48	0.2205	0.5963	0.6370	0.032*
C49	0.0412 (3)	0.70331 (15)	0.61304 (14)	0.0322 (5)
H49	0.0521	0.7246	0.6575	0.039*
C50	−0.0749 (3)	0.74784 (15)	0.55999 (16)	0.0350 (5)
C51	−0.0927 (3)	0.71553 (15)	0.49644 (15)	0.0331 (5)
H51	−0.1743	0.7454	0.4613	0.040*
C52	0.0079 (3)	0.64018 (14)	0.48423 (14)	0.0286 (5)
H52	−0.0052	0.6184	0.4406	0.034*
C53	0.6650 (4)	0.4001 (2)	0.03212 (18)	0.0549 (8)
H53A	0.7324	0.3475	0.0664	0.082*
H53B	0.7131	0.4161	−0.0307	0.082*
H53C	0.5583	0.3865	0.0396	0.082*
C54	−0.1509 (5)	0.8709 (2)	0.6159 (2)	0.0698 (10)
H54A	−0.1665	0.8343	0.6786	0.105*
H54B	−0.2261	0.9276	0.6074	0.105*
H54C	−0.0410	0.8829	0.5974	0.105*
H28	0.310 (3)	0.1298 (18)	0.8226 (18)	0.046 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0630 (12)	0.0479 (10)	0.0225 (8)	−0.0016 (9)	−0.0099 (8)	−0.0122 (7)
O2	0.0579 (12)	0.0405 (10)	0.0752 (14)	−0.0190 (9)	0.0020 (10)	−0.0331 (10)
O3	0.0655 (13)	0.0484 (11)	0.0255 (9)	−0.0127 (9)	0.0099 (8)	−0.0125 (8)
O4	0.0649 (13)	0.0432 (11)	0.0705 (14)	0.0249 (9)	−0.0314 (11)	−0.0344 (10)
N1	0.0265 (9)	0.0229 (9)	0.0203 (8)	−0.0044 (7)	−0.0040 (7)	−0.0018 (7)
N2	0.0372 (11)	0.0264 (9)	0.0211 (9)	−0.0055 (8)	−0.0084 (8)	0.0011 (7)
N3	0.0286 (9)	0.0212 (8)	0.0205 (8)	−0.0058 (7)	−0.0047 (7)	−0.0028 (7)
N4	0.0354 (10)	0.0269 (10)	0.0212 (9)	−0.0079 (8)	−0.0002 (8)	0.0006 (8)
C1	0.0251 (10)	0.0241 (10)	0.0209 (10)	−0.0036 (8)	−0.0043 (8)	−0.0039 (8)
C2	0.0293 (11)	0.0219 (10)	0.0223 (10)	−0.0045 (8)	−0.0049 (8)	−0.0043 (8)
C3	0.0231 (10)	0.0220 (10)	0.0220 (10)	−0.0029 (8)	−0.0035 (8)	−0.0012 (8)
C4	0.0284 (11)	0.0248 (10)	0.0200 (10)	−0.0037 (9)	−0.0038 (8)	−0.0042 (8)
C5	0.0247 (10)	0.0223 (10)	0.0233 (10)	−0.0012 (8)	−0.0048 (8)	−0.0053 (8)
C6	0.0286 (11)	0.0245 (10)	0.0207 (10)	−0.0082 (9)	−0.0023 (8)	−0.0031 (8)
C7	0.0296 (11)	0.0273 (11)	0.0246 (11)	−0.0045 (9)	−0.0021 (9)	−0.0047 (9)
C8	0.0361 (12)	0.0322 (12)	0.0244 (11)	−0.0036 (10)	−0.0089 (9)	0.0001 (9)
C9	0.0440 (13)	0.0371 (13)	0.0190 (10)	−0.0092 (11)	−0.0044 (9)	−0.0066 (9)
C10	0.0554 (16)	0.0286 (12)	0.0281 (12)	0.0011 (11)	−0.0081 (11)	−0.0103 (10)
C11	0.0490 (14)	0.0251 (11)	0.0241 (11)	−0.0042 (10)	−0.0080 (10)	−0.0033 (9)
C12	0.0299 (11)	0.0211 (10)	0.0204 (10)	−0.0035 (8)	−0.0045 (8)	−0.0026 (8)
C13	0.0366 (12)	0.0269 (11)	0.0227 (10)	−0.0081 (9)	−0.0057 (9)	−0.0030 (9)
C14	0.0254 (10)	0.0234 (10)	0.0204 (10)	−0.0014 (8)	−0.0009 (8)	−0.0019 (8)
C15	0.0305 (11)	0.0219 (10)	0.0285 (11)	−0.0026 (9)	0.0001 (9)	0.0016 (9)
C16	0.0367 (13)	0.0246 (11)	0.0375 (13)	−0.0098 (10)	0.0019 (10)	−0.0055 (10)
C17	0.0348 (12)	0.0354 (13)	0.0343 (12)	−0.0117 (10)	−0.0031 (10)	−0.0105 (10)
C18	0.0296 (11)	0.0296 (11)	0.0220 (10)	−0.0054 (9)	−0.0046 (9)	−0.0036 (9)
C19	0.0237 (10)	0.0207 (10)	0.0197 (10)	−0.0025 (8)	−0.0001 (8)	−0.0024 (8)
C20	0.0290 (11)	0.0198 (10)	0.0224 (10)	−0.0019 (8)	−0.0078 (8)	−0.0016 (8)
C21	0.0306 (11)	0.0233 (10)	0.0234 (10)	−0.0054 (9)	−0.0060 (9)	−0.0026 (8)
C22	0.0370 (12)	0.0314 (12)	0.0276 (11)	−0.0050 (10)	−0.0059 (10)	−0.0095 (9)
C23	0.0419 (13)	0.0254 (11)	0.0399 (13)	−0.0074 (10)	−0.0090 (11)	−0.0111 (10)
C24	0.0305 (12)	0.0277 (11)	0.0412 (13)	−0.0092 (9)	−0.0045 (10)	−0.0062 (10)
C25	0.0286 (11)	0.0260 (11)	0.0290 (11)	−0.0046 (9)	−0.0023 (9)	−0.0060 (9)
C26	0.073 (2)	0.0508 (16)	0.0326 (14)	−0.0051 (14)	−0.0077 (13)	−0.0212 (12)
C27	0.078 (2)	0.0473 (17)	0.076 (2)	−0.0160 (16)	0.0063 (18)	−0.0396 (16)
C28	0.0267 (10)	0.0213 (10)	0.0225 (10)	−0.0044 (8)	−0.0050 (8)	−0.0037 (8)
C29	0.0272 (11)	0.0204 (10)	0.0233 (10)	−0.0031 (8)	−0.0040 (8)	−0.0048 (8)
C30	0.0258 (10)	0.0211 (10)	0.0210 (10)	−0.0062 (8)	−0.0053 (8)	−0.0022 (8)
C31	0.0282 (11)	0.0239 (10)	0.0191 (9)	−0.0044 (8)	−0.0039 (8)	−0.0051 (8)
C32	0.0246 (10)	0.0200 (10)	0.0230 (10)	−0.0052 (8)	−0.0056 (8)	−0.0041 (8)
C33	0.0258 (10)	0.0258 (10)	0.0198 (10)	−0.0018 (8)	−0.0059 (8)	−0.0029 (8)
C34	0.0311 (11)	0.0270 (11)	0.0244 (10)	−0.0042 (9)	−0.0072 (9)	−0.0036 (9)
C35	0.0358 (12)	0.0309 (12)	0.0238 (11)	−0.0101 (10)	−0.0015 (9)	0.0002 (9)
C36	0.0368 (13)	0.0379 (13)	0.0224 (11)	−0.0036 (10)	0.0002 (9)	−0.0061 (9)
C37	0.0574 (16)	0.0314 (12)	0.0280 (12)	−0.0051 (11)	−0.0018 (11)	−0.0115 (10)
C38	0.0453 (14)	0.0257 (11)	0.0237 (11)	−0.0056 (10)	−0.0015 (10)	−0.0049 (9)
C39	0.0309 (11)	0.0218 (10)	0.0183 (9)	−0.0040 (8)	−0.0027 (8)	−0.0035 (8)
C40	0.0331 (12)	0.0264 (11)	0.0216 (10)	−0.0028 (9)	−0.0017 (9)	−0.0020 (8)
C41	0.0313 (11)	0.0219 (10)	0.0211 (10)	−0.0076 (9)	−0.0061 (8)	−0.0022 (8)
C42	0.0401 (13)	0.0211 (10)	0.0259 (11)	−0.0071 (9)	−0.0113 (10)	0.0019 (8)
C43	0.0389 (13)	0.0252 (11)	0.0340 (12)	0.0019 (10)	−0.0141 (10)	−0.0055 (9)
C44	0.0323 (12)	0.0359 (13)	0.0282 (11)	−0.0025 (10)	−0.0064 (9)	−0.0086 (10)
C45	0.0311 (11)	0.0274 (11)	0.0221 (10)	−0.0062 (9)	−0.0051 (9)	−0.0026 (8)
C46	0.0302 (11)	0.0196 (10)	0.0189 (9)	−0.0058 (8)	−0.0063 (8)	−0.0031 (8)
C47	0.0277 (11)	0.0186 (10)	0.0223 (10)	−0.0070 (8)	−0.0004 (8)	−0.0027 (8)
C48	0.0283 (11)	0.0235 (10)	0.0234 (10)	−0.0030 (8)	−0.0039 (8)	−0.0034 (8)
C49	0.0410 (13)	0.0296 (11)	0.0248 (11)	−0.0043 (10)	−0.0044 (9)	−0.0092 (9)
C50	0.0354 (13)	0.0259 (11)	0.0384 (13)	0.0046 (10)	−0.0061 (10)	−0.0108 (10)
C51	0.0311 (12)	0.0280 (11)	0.0379 (13)	0.0016 (9)	−0.0135 (10)	−0.0076 (10)
C52	0.0308 (11)	0.0251 (11)	0.0287 (11)	−0.0065 (9)	−0.0063 (9)	−0.0055 (9)
C53	0.068 (2)	0.0581 (18)	0.0330 (14)	−0.0049 (15)	0.0082 (13)	−0.0221 (13)
C54	0.102 (3)	0.0461 (17)	0.068 (2)	0.0250 (17)	−0.036 (2)	−0.0373 (16)

Geometric parameters (Å, º) top

O1—C9	1.370 (3)	C24—C25	1.376 (3)
O1—C26	1.424 (3)	C24—H24	0.95
O2—C23	1.367 (3)	C25—H25	0.95
O2—C27	1.420 (3)	C26—H26A	0.98
O3—C36	1.368 (3)	C26—H26B	0.98
O3—C53	1.424 (3)	C26—H26C	0.98
O4—C50	1.369 (3)	C27—H27A	0.98
O4—C54	1.420 (3)	C27—H27B	0.98
N1—C1	1.350 (3)	C27—H27C	0.98
N1—C5	1.352 (3)	C28—C29	1.390 (3)
N2—C13	1.361 (3)	C28—C33	1.488 (3)
N2—C14	1.376 (3)	C29—C30	1.395 (3)
N2—H1	0.94 (3)	C29—H29	0.95
N3—C28	1.349 (3)	C30—C31	1.393 (3)
N3—C32	1.353 (3)	C30—C39	1.466 (3)
N4—C40	1.363 (3)	C31—C32	1.389 (3)
N4—C41	1.374 (3)	C31—H31	0.95
N4—H28	0.91 (3)	C32—C47	1.481 (3)
C1—C2	1.391 (3)	C33—C38	1.386 (3)
C1—C6	1.486 (3)	C33—C34	1.398 (3)
C2—C3	1.390 (3)	C34—C35	1.381 (3)
C2—H2	0.95	C34—H34	0.95
C3—C4	1.396 (3)	C35—C36	1.388 (3)
C3—C12	1.464 (3)	C35—H35	0.95
C4—C5	1.391 (3)	C36—C37	1.388 (3)
C4—H4	0.95	C37—C38	1.390 (3)
C5—C20	1.484 (3)	C37—H37	0.95
C6—C11	1.388 (3)	C38—H38	0.95
C6—C7	1.400 (3)	C39—C40	1.376 (3)
C7—C8	1.381 (3)	C39—C46	1.440 (3)
C7—H7	0.95	C40—H40	0.95
C8—C9	1.386 (3)	C41—C42	1.391 (3)
C8—H8	0.95	C41—C46	1.415 (3)
C9—C10	1.386 (3)	C42—C43	1.371 (3)
C10—C11	1.393 (3)	C42—H42	0.95
C10—H10	0.95	C43—C44	1.399 (3)
C11—H11	0.95	C43—H43	0.95
C12—C13	1.378 (3)	C44—C45	1.381 (3)
C12—C19	1.447 (3)	C44—H44	0.95
C13—H13	0.95	C45—C46	1.398 (3)
C14—C15	1.390 (3)	C45—H45	0.95
C14—C19	1.417 (3)	C47—C48	1.391 (3)
C15—C16	1.377 (3)	C47—C52	1.398 (3)
C15—H15	0.95	C48—C49	1.388 (3)
C16—C17	1.401 (3)	C48—H48	0.95
C16—H16	0.95	C49—C50	1.387 (3)
C17—C18	1.379 (3)	C49—H49	0.95
C17—H17	0.95	C50—C51	1.386 (3)
C18—C19	1.400 (3)	C51—C52	1.377 (3)
C18—H18	0.95	C51—H51	0.95
C20—C21	1.385 (3)	C52—H52	0.95
C20—C25	1.401 (3)	C53—H53A	0.98
C21—C22	1.395 (3)	C53—H53B	0.98
C21—H21	0.95	C53—H53C	0.98
C22—C23	1.387 (3)	C54—H54A	0.98
C22—H22	0.95	C54—H54B	0.98
C23—C24	1.388 (3)	C54—H54C	0.98

C9—O1—C26	117.57 (19)	O2—C27—H27A	109.5
C23—O2—C27	118.1 (2)	O2—C27—H27B	109.5
C36—O3—C53	117.5 (2)	H27A—C27—H27B	109.5
C50—O4—C54	118.5 (2)	O2—C27—H27C	109.5
C1—N1—C5	117.33 (17)	H27A—C27—H27C	109.5
C13—N2—C14	109.06 (18)	H27B—C27—H27C	109.5
C13—N2—H1	127.1 (18)	N3—C28—C29	122.48 (19)
C14—N2—H1	123.5 (18)	N3—C28—C33	117.47 (17)
C28—N3—C32	117.43 (17)	C29—C28—C33	120.06 (18)
C40—N4—C41	109.07 (18)	C28—C29—C30	120.55 (19)
C40—N4—H28	127.1 (17)	C28—C29—H29	119.7
C41—N4—H28	123.5 (17)	C30—C29—H29	119.7
N1—C1—C2	122.44 (18)	C31—C30—C29	116.47 (18)
N1—C1—C6	117.53 (17)	C31—C30—C39	122.14 (18)
C2—C1—C6	120.03 (18)	C29—C30—C39	121.24 (18)
C3—C2—C1	120.75 (19)	C32—C31—C30	120.43 (19)
C3—C2—H2	119.6	C32—C31—H31	119.8
C1—C2—H2	119.6	C30—C31—H31	119.8
C2—C3—C4	116.44 (18)	N3—C32—C31	122.60 (18)
C2—C3—C12	121.79 (19)	N3—C32—C47	116.77 (17)
C4—C3—C12	121.62 (18)	C31—C32—C47	120.60 (18)
C5—C4—C3	120.31 (19)	C38—C33—C34	117.95 (19)
C5—C4—H4	119.8	C38—C33—C28	120.92 (18)
C3—C4—H4	119.8	C34—C33—C28	121.11 (19)
N1—C5—C4	122.70 (19)	C35—C34—C33	120.9 (2)
N1—C5—C20	117.17 (17)	C35—C34—H34	119.6
C4—C5—C20	120.09 (18)	C33—C34—H34	119.6
C11—C6—C7	117.96 (19)	C34—C35—C36	120.4 (2)
C11—C6—C1	120.60 (18)	C34—C35—H35	119.8
C7—C6—C1	121.44 (19)	C36—C35—H35	119.8
C8—C7—C6	120.7 (2)	O3—C36—C35	115.7 (2)
C8—C7—H7	119.7	O3—C36—C37	124.6 (2)
C6—C7—H7	119.7	C35—C36—C37	119.6 (2)
C7—C8—C9	120.5 (2)	C36—C37—C38	119.4 (2)
C7—C8—H8	119.7	C36—C37—H37	120.3
C9—C8—H8	119.7	C38—C37—H37	120.3
O1—C9—C10	124.4 (2)	C33—C38—C37	121.7 (2)
O1—C9—C8	115.8 (2)	C33—C38—H38	119.1
C10—C9—C8	119.9 (2)	C37—C38—H38	119.1
C9—C10—C11	119.2 (2)	C40—C39—C46	106.27 (17)
C9—C10—H10	120.4	C40—C39—C30	125.05 (19)
C11—C10—H10	120.4	C46—C39—C30	128.39 (18)
C6—C11—C10	121.8 (2)	N4—C40—C39	110.25 (19)
C6—C11—H11	119.1	N4—C40—H40	124.9
C10—C11—H11	119.1	C39—C40—H40	124.9
C13—C12—C19	106.06 (17)	N4—C41—C42	129.72 (19)
C13—C12—C3	124.99 (19)	N4—C41—C46	107.83 (18)
C19—C12—C3	128.62 (18)	C42—C41—C46	122.5 (2)
N2—C13—C12	110.49 (19)	C43—C42—C41	117.4 (2)
N2—C13—H13	124.8	C43—C42—H42	121.3
C12—C13—H13	124.8	C41—C42—H42	121.3
N2—C14—C15	129.67 (19)	C42—C43—C44	121.4 (2)
N2—C14—C19	107.93 (18)	C42—C43—H43	119.3
C15—C14—C19	122.4 (2)	C44—C43—H43	119.3
C16—C15—C14	117.3 (2)	C45—C44—C43	121.3 (2)
C16—C15—H15	121.3	C45—C44—H44	119.3
C14—C15—H15	121.3	C43—C44—H44	119.3
C15—C16—C17	121.5 (2)	C44—C45—C46	118.8 (2)
C15—C16—H16	119.3	C44—C45—H45	120.6
C17—C16—H16	119.3	C46—C45—H45	120.6
C18—C17—C16	121.1 (2)	C45—C46—C41	118.53 (19)
C18—C17—H17	119.5	C45—C46—C39	134.79 (19)
C16—C17—H17	119.5	C41—C46—C39	106.56 (18)
C17—C18—C19	119.1 (2)	C48—C47—C52	118.10 (19)
C17—C18—H18	120.5	C48—C47—C32	121.30 (19)
C19—C18—H18	120.5	C52—C47—C32	120.60 (19)
C18—C19—C14	118.57 (19)	C49—C48—C47	121.4 (2)
C18—C19—C12	134.90 (19)	C49—C48—H48	119.3
C14—C19—C12	106.42 (18)	C47—C48—H48	119.3
C21—C20—C25	118.28 (19)	C50—C49—C48	119.2 (2)
C21—C20—C5	121.23 (19)	C50—C49—H49	120.4
C25—C20—C5	120.48 (19)	C48—C49—H49	120.4
C20—C21—C22	121.5 (2)	O4—C50—C51	114.8 (2)
C20—C21—H21	119.3	O4—C50—C49	125.0 (2)
C22—C21—H21	119.3	C51—C50—C49	120.3 (2)
C23—C22—C21	119.2 (2)	C52—C51—C50	120.0 (2)
C23—C22—H22	120.4	C52—C51—H51	120.0
C21—C22—H22	120.4	C50—C51—H51	120.0
O2—C23—C22	124.6 (2)	C51—C52—C47	121.0 (2)
O2—C23—C24	115.4 (2)	C51—C52—H52	119.5
C22—C23—C24	120.0 (2)	C47—C52—H52	119.5
C25—C24—C23	120.4 (2)	O3—C53—H53A	109.5
C25—C24—H24	119.8	O3—C53—H53B	109.5
C23—C24—H24	119.8	H53A—C53—H53B	109.5
C24—C25—C20	120.7 (2)	O3—C53—H53C	109.5
C24—C25—H25	119.7	H53A—C53—H53C	109.5
C20—C25—H25	119.7	H53B—C53—H53C	109.5
O1—C26—H26A	109.5	O4—C54—H54A	109.5
O1—C26—H26B	109.5	O4—C54—H54B	109.5
H26A—C26—H26B	109.5	H54A—C54—H54B	109.5
O1—C26—H26C	109.5	O4—C54—H54C	109.5
H26A—C26—H26C	109.5	H54A—C54—H54C	109.5
H26B—C26—H26C	109.5	H54B—C54—H54C	109.5

C5—N1—C1—C2	0.1 (3)	C32—N3—C28—C29	0.7 (3)
C5—N1—C1—C6	−179.42 (18)	C32—N3—C28—C33	−179.41 (18)
N1—C1—C2—C3	−0.6 (3)	N3—C28—C29—C30	0.3 (3)
C6—C1—C2—C3	178.94 (19)	C33—C28—C29—C30	−179.63 (19)
C1—C2—C3—C4	1.5 (3)	C28—C29—C30—C31	−1.6 (3)
C1—C2—C3—C12	−174.00 (19)	C28—C29—C30—C39	174.17 (19)
C2—C3—C4—C5	−2.1 (3)	C29—C30—C31—C32	2.0 (3)
C12—C3—C4—C5	173.47 (19)	C39—C30—C31—C32	−173.74 (19)
C1—N1—C5—C4	−0.7 (3)	C28—N3—C32—C31	−0.2 (3)
C1—N1—C5—C20	177.05 (18)	C28—N3—C32—C47	−178.56 (18)
C3—C4—C5—N1	1.7 (3)	C30—C31—C32—N3	−1.1 (3)
C3—C4—C5—C20	−175.94 (19)	C30—C31—C32—C47	177.13 (19)
N1—C1—C6—C11	136.2 (2)	N3—C28—C33—C38	−139.9 (2)
C2—C1—C6—C11	−43.3 (3)	C29—C28—C33—C38	40.1 (3)
N1—C1—C6—C7	−44.6 (3)	N3—C28—C33—C34	41.7 (3)
C2—C1—C6—C7	135.9 (2)	C29—C28—C33—C34	−138.3 (2)
C11—C6—C7—C8	−0.1 (3)	C38—C33—C34—C35	0.3 (3)
C1—C6—C7—C8	−179.4 (2)	C28—C33—C34—C35	178.7 (2)
C6—C7—C8—C9	0.3 (3)	C33—C34—C35—C36	−1.0 (3)
C26—O1—C9—C10	−2.8 (4)	C53—O3—C36—C35	−178.7 (2)
C26—O1—C9—C8	177.3 (2)	C53—O3—C36—C37	1.4 (4)
C7—C8—C9—O1	179.4 (2)	C34—C35—C36—O3	−178.8 (2)
C7—C8—C9—C10	−0.4 (4)	C34—C35—C36—C37	1.2 (4)
O1—C9—C10—C11	−179.5 (2)	O3—C36—C37—C38	179.3 (2)
C8—C9—C10—C11	0.3 (4)	C35—C36—C37—C38	−0.6 (4)
C7—C6—C11—C10	0.0 (3)	C34—C33—C38—C37	0.3 (3)
C1—C6—C11—C10	179.3 (2)	C28—C33—C38—C37	−178.2 (2)
C9—C10—C11—C6	−0.1 (4)	C36—C37—C38—C33	−0.1 (4)
C2—C3—C12—C13	144.2 (2)	C31—C30—C39—C40	31.9 (3)
C4—C3—C12—C13	−31.2 (3)	C29—C30—C39—C40	−143.6 (2)
C2—C3—C12—C19	−28.4 (3)	C31—C30—C39—C46	−155.1 (2)
C4—C3—C12—C19	156.3 (2)	C29—C30—C39—C46	29.4 (3)
C14—N2—C13—C12	0.5 (3)	C41—N4—C40—C39	0.0 (3)
C19—C12—C13—N2	0.7 (2)	C46—C39—C40—N4	−0.9 (2)
C3—C12—C13—N2	−173.2 (2)	C30—C39—C40—N4	173.39 (19)
C13—N2—C14—C15	−179.9 (2)	C40—N4—C41—C42	−179.9 (2)
C13—N2—C14—C19	−1.6 (2)	C40—N4—C41—C46	0.9 (2)
N2—C14—C15—C16	175.6 (2)	N4—C41—C42—C43	−176.6 (2)
C19—C14—C15—C16	−2.4 (3)	C46—C41—C42—C43	2.6 (3)
C14—C15—C16—C17	0.0 (3)	C41—C42—C43—C44	0.3 (3)
C15—C16—C17—C18	1.2 (4)	C42—C43—C44—C45	−1.6 (4)
C16—C17—C18—C19	0.1 (3)	C43—C44—C45—C46	−0.1 (3)
C17—C18—C19—C14	−2.4 (3)	C44—C45—C46—C41	2.8 (3)
C17—C18—C19—C12	−178.0 (2)	C44—C45—C46—C39	178.1 (2)
N2—C14—C19—C18	−174.70 (18)	N4—C41—C46—C45	175.15 (18)
C15—C14—C19—C18	3.7 (3)	C42—C41—C46—C45	−4.2 (3)
N2—C14—C19—C12	2.0 (2)	N4—C41—C46—C39	−1.4 (2)
C15—C14—C19—C12	−179.59 (19)	C42—C41—C46—C39	179.3 (2)
C13—C12—C19—C18	174.3 (2)	C40—C39—C46—C45	−174.4 (2)
C3—C12—C19—C18	−12.1 (4)	C30—C39—C46—C45	11.7 (4)
C13—C12—C19—C14	−1.7 (2)	C40—C39—C46—C41	1.4 (2)
C3—C12—C19—C14	172.0 (2)	C30—C39—C46—C41	−172.6 (2)
N1—C5—C20—C21	139.9 (2)	N3—C32—C47—C48	−137.3 (2)
C4—C5—C20—C21	−42.3 (3)	C31—C32—C47—C48	44.3 (3)
N1—C5—C20—C25	−41.3 (3)	N3—C32—C47—C52	42.6 (3)
C4—C5—C20—C25	136.5 (2)	C31—C32—C47—C52	−135.7 (2)
C25—C20—C21—C22	1.4 (3)	C52—C47—C48—C49	−2.3 (3)
C5—C20—C21—C22	−179.77 (19)	C32—C47—C48—C49	177.68 (19)
C20—C21—C22—C23	−0.8 (3)	C47—C48—C49—C50	0.6 (3)
C27—O2—C23—C22	−13.0 (4)	C54—O4—C50—C51	−169.1 (3)
C27—O2—C23—C24	167.4 (3)	C54—O4—C50—C49	10.5 (4)
C21—C22—C23—O2	179.8 (2)	C48—C49—C50—O4	−178.2 (2)
C21—C22—C23—C24	−0.6 (3)	C48—C49—C50—C51	1.4 (4)
O2—C23—C24—C25	−179.0 (2)	O4—C50—C51—C52	178.0 (2)
C22—C23—C24—C25	1.4 (4)	C49—C50—C51—C52	−1.6 (4)
C23—C24—C25—C20	−0.8 (3)	C50—C51—C52—C47	−0.1 (3)
C21—C20—C25—C24	−0.6 (3)	C48—C47—C52—C51	2.0 (3)
C5—C20—C25—C24	−179.5 (2)	C32—C47—C52—C51	−178.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H28···N1ⁱ	0.91 (3)	2.12 (3)	3.001 (3)	163 (2)
N2—H1···N3ⁱⁱ	0.94 (3)	2.10 (3)	3.018 (2)	165 (3)

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

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