1-[(E)-3-sec-Butyl-4-(4′-eth­oxy-3,5-diethyl­biphenyl-4-yldiazen­yl)phen­oxy]hexa­deca­ne

Han, M.R.; Hashizume, D.; Hara, M.

doi:10.1107/S1600536806023270

1-[(E)-3-sec-Butyl-4-(4′-ethoxy-3,5-diethylbiphenyl-4-yldiazenyl)phenoxy]hexadecane

A Suzuki coupling reaction produced the title compound, C₄₄H₆₆N₂O₂, which consists of a photoisomerizable azobenzene unit coupled to a biphenyl group and a long alkyl chain. The molecule has a trans configuration with respect to the azo (–N=N–) group, and the long alkyl chain adopts a well ordered zigzag arrangement.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806023270/is2058sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806023270/is2058Isup2.hkl Contains datablock I

CCDC reference: 613742

checkCIF report

Key indicators

Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R factor = 0.047
wR factor = 0.128
Data-to-parameter ratio = 24.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.14 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.71 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C8     -   C9     ...       1.38 Ang.
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H19B   ..  H26E    ..       2.12 Ang.

   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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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 SM (Rigaku/MSC Inc., 2005); cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data reduction: HKL-2000; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

[(E)-3-sec-Butyl-4-(4'-Ethoxy-3,5-diethylbiphenyl-4- yldiazenyl)phenoxy]hexadecane top

Crystal data top

C₄₄H₆₆N₂O₂	F(000) = 1440
M_r = 654.99	D_x = 1.086 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 196669 reflections
a = 22.0464 (3) Å	θ = 1.0–30.1°
b = 9.9446 (1) Å	µ = 0.07 mm⁻¹
c = 18.8628 (3) Å	T = 90 K
β = 104.3701 (5)°	Needle, orange
V = 4006.14 (9) Å³	0.40 × 0.15 × 0.04 mm
Z = 4

Data collection top

Rigaku AFC-8 with Saturn 70 CCD diffractometer	9044 reflections with I > 2σ(I)
Radiation source: fine-focus rotating anode	R_int = 0.025
Confocal monochromator	θ_max = 30.1°, θ_min = 1.0°
Detector resolution: 28.5714 pixels mm^-1	h = −31→31
ω scans	k = −14→12
22050 measured reflections	l = −26→26
11745 independent 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)] = 0.047	Hydrogen site location: difference Fourier map
wR(F²) = 0.128	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0566P)² + 1.1001P] where P = (F_o² + 2F_c²)/3
11745 reflections	(Δ/σ)_max = 0.001
480 parameters	Δρ_max = 0.30 e Å⁻³
8 restraints	Δρ_min = −0.24 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	Occ. (<1)
O1	0.48797 (4)	−0.58849 (8)	0.09936 (5)	0.03018 (19)
O2	0.20305 (4)	0.87427 (7)	0.18575 (4)	0.02413 (16)
N1	0.30073 (4)	0.29144 (9)	0.16929 (5)	0.02144 (18)
N2	0.29412 (4)	0.38074 (9)	0.12051 (5)	0.02320 (18)
C1	0.32717 (5)	0.16792 (11)	0.15298 (6)	0.0210 (2)
C2	0.32401 (5)	0.11705 (12)	0.08227 (6)	0.0249 (2)
C3	0.35119 (5)	−0.00831 (12)	0.07700 (6)	0.0259 (2)
H3	0.3489	−0.0440	0.0297	0.031*
C4	0.38144 (5)	−0.08351 (11)	0.13790 (6)	0.0222 (2)
C5	0.38342 (5)	−0.03007 (11)	0.20713 (6)	0.0222 (2)
H5	0.4039	−0.0795	0.2494	0.027*
C6	0.35633 (5)	0.09321 (11)	0.21575 (6)	0.0211 (2)
C7	0.26959 (5)	0.50414 (10)	0.13928 (6)	0.0206 (2)
C8	0.26390 (5)	0.53615 (10)	0.20979 (5)	0.01994 (19)
H8	0.2752	0.4712	0.2477	0.024*
C9	0.24219 (5)	0.66067 (10)	0.22508 (5)	0.01884 (19)
C10	0.22477 (5)	0.75423 (10)	0.16714 (6)	0.02012 (19)
C11	0.23007 (5)	0.72306 (11)	0.09700 (6)	0.0235 (2)
H11	0.2178	0.7865	0.0585	0.028*
C12	0.25347 (5)	0.59834 (11)	0.08381 (6)	0.0241 (2)
H12	0.2584	0.5776	0.0364	0.029*
C13	0.40949 (5)	−0.21641 (11)	0.12933 (6)	0.0226 (2)
C14	0.43510 (5)	−0.24328 (11)	0.06968 (6)	0.0249 (2)
H14	0.4349	−0.1747	0.0346	0.030*
C15	0.46055 (5)	−0.36748 (11)	0.06085 (6)	0.0266 (2)
H15	0.4775	−0.3836	0.0200	0.032*
C16	0.46132 (5)	−0.46893 (11)	0.11205 (6)	0.0248 (2)
C17	0.43635 (5)	−0.44503 (11)	0.17172 (6)	0.0257 (2)
H17	0.4368	−0.5137	0.2069	0.031*
C18	0.41060 (5)	−0.31958 (11)	0.17955 (6)	0.0245 (2)
H18	0.3934	−0.3040	0.2202	0.029*
C19	0.29157 (7)	0.18548 (14)	0.01156 (6)	0.0389 (3)
H19A	0.2563	0.2398	0.0199	0.047*
H19B	0.2739	0.1160	−0.0254	0.047*
C20	0.33487 (8)	0.27638 (19)	−0.01873 (8)	0.0593 (5)
H20A	0.3494	0.3506	0.0154	0.089*
H20B	0.3121	0.3127	−0.0662	0.089*
H20C	0.3709	0.2243	−0.0249	0.089*
C21	0.36090 (5)	0.14751 (11)	0.29189 (6)	0.0240 (2)
H21A	0.3755	0.0748	0.3279	0.029*
H21B	0.3186	0.1750	0.2956	0.029*
C22	0.40526 (5)	0.26742 (12)	0.31147 (6)	0.0276 (2)
H22A	0.4464	0.2431	0.3044	0.041*
H22B	0.4095	0.2923	0.3627	0.041*
H22C	0.3883	0.3438	0.2799	0.041*
C23A	0.23920 (5)	0.70218 (10)	0.30157 (5)	0.0213 (2)	0.633 (2)
H23A	0.2041	0.7679	0.2966	0.026*	0.633 (2)
C24A	0.22535 (11)	0.5822 (2)	0.34673 (11)	0.0231 (5)	0.633 (2)
H24A	0.2607	0.5195	0.3560	0.035*	0.633 (2)
H24B	0.1874	0.5360	0.3195	0.035*	0.633 (2)
H24C	0.2190	0.6147	0.3934	0.035*	0.633 (2)
C25A	0.29958 (13)	0.7743 (2)	0.33929 (13)	0.0294 (6)	0.633 (2)
H25A	0.3341	0.7080	0.3504	0.035*	0.633 (2)
H25B	0.3095	0.8415	0.3051	0.035*	0.633 (2)
C26A	0.29641 (10)	0.8451 (2)	0.40982 (10)	0.0352 (4)	0.633 (2)
H26A	0.2598	0.9043	0.4004	0.053*	0.633 (2)
H26B	0.3345	0.8985	0.4279	0.053*	0.633 (2)
H26C	0.2930	0.7780	0.4467	0.053*	0.633 (2)
C23B	0.23920 (5)	0.70218 (10)	0.30157 (5)	0.0213 (2)	0.367 (2)
H23B	0.1992	0.7526	0.2972	0.026*	0.367 (2)
C24B	0.2934 (2)	0.7996 (4)	0.3325 (3)	0.0231 (5)	0.367 (2)
H24D	0.3334	0.7529	0.3372	0.035*	0.367 (2)
H24E	0.2905	0.8316	0.3807	0.035*	0.367 (2)
H24F	0.2909	0.8763	0.2993	0.035*	0.367 (2)
C25B	0.2401 (2)	0.5870 (6)	0.3539 (2)	0.0294 (6)	0.367 (2)
H25C	0.2820	0.5447	0.3653	0.035*	0.367 (2)
H25D	0.2092	0.5186	0.3298	0.035*	0.367 (2)
C26B	0.22500 (18)	0.6307 (4)	0.42520 (16)	0.0352 (4)	0.367 (2)
H26D	0.2619	0.6733	0.4571	0.053*	0.367 (2)
H26E	0.2131	0.5519	0.4499	0.053*	0.367 (2)
H26F	0.1902	0.6951	0.4144	0.053*	0.367 (2)
C27	0.47893 (6)	−0.70248 (11)	0.14211 (7)	0.0277 (2)
H27A	0.4337	−0.7166	0.1380	0.033*
H27B	0.5002	−0.6880	0.1943	0.033*
C28	0.50640 (6)	−0.82329 (12)	0.11272 (8)	0.0351 (3)
H28A	0.4842	−0.8380	0.0615	0.053*
H28B	0.5019	−0.9029	0.1416	0.053*
H28C	0.5509	−0.8073	0.1160	0.053*
C29	0.18237 (5)	0.97371 (10)	0.12989 (6)	0.0231 (2)
H29A	0.1462	0.9399	0.0919	0.028*
H29B	0.2165	0.9967	0.1064	0.028*
C30	0.16379 (5)	1.09560 (10)	0.16766 (6)	0.0231 (2)
H30A	0.2010	1.1290	0.2044	0.028*
H30B	0.1322	1.0683	0.1940	0.028*
C31	0.13712 (5)	1.20958 (11)	0.11515 (6)	0.0240 (2)
H31A	0.1002	1.1766	0.0779	0.029*
H31B	0.1689	1.2392	0.0896	0.029*
C32	0.11792 (5)	1.32890 (10)	0.15587 (6)	0.0231 (2)
H32A	0.0858	1.2984	0.1808	0.028*
H32B	0.1548	1.3589	0.1941	0.028*
C33	0.09208 (5)	1.44853 (11)	0.10725 (6)	0.0244 (2)
H33A	0.0554	1.4190	0.0685	0.029*
H33B	0.1244	1.4810	0.0831	0.029*
C34	0.07244 (5)	1.56413 (10)	0.14997 (6)	0.0225 (2)
H34A	0.0405	1.5309	0.1744	0.027*
H34B	0.1092	1.5935	0.1886	0.027*
C35	0.04595 (5)	1.68515 (11)	0.10270 (6)	0.0245 (2)
H35A	0.0087	1.6564	0.0646	0.029*
H35B	0.0776	1.7179	0.0777	0.029*
C36	0.02748 (5)	1.80060 (10)	0.14650 (6)	0.0231 (2)
H36A	−0.0018	1.7660	0.1744	0.028*
H36B	0.0654	1.8335	0.1822	0.028*
C37	−0.00332 (5)	1.91822 (11)	0.09927 (6)	0.0252 (2)
H37A	−0.0413	1.8854	0.0636	0.030*
H37B	0.0259	1.9528	0.0713	0.030*
C38	−0.02167 (5)	2.03365 (11)	0.14336 (6)	0.0240 (2)
H38A	−0.0516	1.9995	0.1705	0.029*
H38B	0.0161	2.0651	0.1798	0.029*
C39	−0.05115 (6)	2.15227 (11)	0.09626 (6)	0.0287 (2)
H39A	−0.0896	2.1213	0.0607	0.034*
H39B	−0.0217	2.1847	0.0681	0.034*
C40	−0.06787 (5)	2.26915 (11)	0.14038 (6)	0.0244 (2)
H40A	−0.0979	2.2370	0.1679	0.029*
H40B	−0.0296	2.2991	0.1765	0.029*
C41	−0.09642 (6)	2.38893 (12)	0.09338 (6)	0.0304 (3)
H41A	−0.0662	2.4214	0.0662	0.036*
H41B	−0.1345	2.3588	0.0570	0.036*
C42	−0.11359 (5)	2.50518 (11)	0.13719 (6)	0.0244 (2)
H42A	−0.0759	2.5327	0.1750	0.029*
H42B	−0.1453	2.4739	0.1626	0.029*
C43	−0.13937 (6)	2.62694 (11)	0.09028 (6)	0.0297 (2)
H43A	−0.1776	2.6000	0.0532	0.036*
H43B	−0.1081	2.6571	0.0640	0.036*
C44	−0.15508 (6)	2.74415 (12)	0.13477 (7)	0.0336 (3)
H44A	−0.1889	2.7178	0.1571	0.050*
H44B	−0.1685	2.8216	0.1025	0.050*
H44C	−0.1179	2.7684	0.1732	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0414 (5)	0.0171 (4)	0.0387 (5)	0.0057 (3)	0.0226 (4)	0.0007 (3)
O2	0.0349 (4)	0.0171 (4)	0.0215 (3)	0.0088 (3)	0.0091 (3)	0.0043 (3)
N1	0.0237 (4)	0.0192 (4)	0.0215 (4)	0.0031 (3)	0.0059 (3)	−0.0023 (3)
N2	0.0295 (4)	0.0198 (4)	0.0217 (4)	0.0023 (4)	0.0088 (3)	−0.0022 (3)
C1	0.0230 (5)	0.0189 (5)	0.0220 (5)	0.0023 (4)	0.0077 (4)	−0.0035 (4)
C2	0.0268 (5)	0.0255 (5)	0.0213 (5)	0.0059 (4)	0.0040 (4)	−0.0044 (4)
C3	0.0292 (5)	0.0259 (6)	0.0220 (5)	0.0057 (4)	0.0052 (4)	−0.0064 (4)
C4	0.0232 (5)	0.0197 (5)	0.0253 (5)	0.0010 (4)	0.0088 (4)	−0.0031 (4)
C5	0.0258 (5)	0.0196 (5)	0.0228 (5)	0.0023 (4)	0.0092 (4)	−0.0002 (4)
C6	0.0246 (5)	0.0191 (5)	0.0215 (5)	−0.0003 (4)	0.0094 (4)	−0.0024 (4)
C7	0.0244 (5)	0.0179 (5)	0.0201 (4)	0.0017 (4)	0.0067 (4)	−0.0015 (4)
C8	0.0240 (5)	0.0183 (5)	0.0182 (4)	0.0028 (4)	0.0065 (4)	0.0017 (4)
C9	0.0223 (4)	0.0175 (5)	0.0176 (4)	0.0022 (4)	0.0065 (3)	0.0005 (4)
C10	0.0237 (5)	0.0158 (5)	0.0214 (5)	0.0025 (4)	0.0066 (4)	0.0015 (4)
C11	0.0315 (5)	0.0205 (5)	0.0184 (4)	0.0024 (4)	0.0059 (4)	0.0034 (4)
C12	0.0329 (5)	0.0224 (5)	0.0179 (4)	0.0007 (4)	0.0082 (4)	−0.0009 (4)
C13	0.0238 (5)	0.0189 (5)	0.0259 (5)	0.0023 (4)	0.0080 (4)	−0.0042 (4)
C14	0.0314 (5)	0.0210 (5)	0.0243 (5)	0.0040 (4)	0.0105 (4)	0.0000 (4)
C15	0.0331 (6)	0.0229 (5)	0.0277 (5)	0.0035 (4)	0.0149 (4)	−0.0022 (4)
C16	0.0281 (5)	0.0177 (5)	0.0312 (5)	0.0016 (4)	0.0124 (4)	−0.0032 (4)
C17	0.0311 (5)	0.0193 (5)	0.0299 (5)	0.0004 (4)	0.0139 (4)	0.0004 (4)
C18	0.0275 (5)	0.0220 (5)	0.0274 (5)	0.0000 (4)	0.0128 (4)	−0.0037 (4)
C19	0.0529 (8)	0.0383 (7)	0.0200 (5)	0.0236 (6)	−0.0017 (5)	−0.0078 (5)
C20	0.0770 (11)	0.0789 (12)	0.0307 (7)	0.0465 (10)	0.0297 (7)	0.0243 (8)
C21	0.0332 (5)	0.0210 (5)	0.0202 (5)	0.0032 (4)	0.0110 (4)	−0.0003 (4)
C22	0.0335 (6)	0.0281 (6)	0.0213 (5)	0.0000 (5)	0.0072 (4)	−0.0034 (4)
C23A	0.0288 (5)	0.0186 (5)	0.0183 (4)	0.0046 (4)	0.0090 (4)	0.0007 (4)
C24A	0.0340 (11)	0.0188 (8)	0.0182 (8)	0.0050 (8)	0.0098 (8)	0.0040 (6)
C25A	0.0313 (10)	0.0325 (12)	0.0227 (10)	0.0014 (9)	0.0037 (7)	−0.0016 (9)
C26A	0.0471 (10)	0.0355 (9)	0.0223 (7)	0.0020 (8)	0.0071 (7)	−0.0071 (7)
C23B	0.0288 (5)	0.0186 (5)	0.0183 (4)	0.0046 (4)	0.0090 (4)	0.0007 (4)
C24B	0.0340 (11)	0.0188 (8)	0.0182 (8)	0.0050 (8)	0.0098 (8)	0.0040 (6)
C25B	0.0313 (10)	0.0325 (12)	0.0227 (10)	0.0014 (9)	0.0037 (7)	−0.0016 (9)
C26B	0.0471 (10)	0.0355 (9)	0.0223 (7)	0.0020 (8)	0.0071 (7)	−0.0071 (7)
C27	0.0312 (5)	0.0192 (5)	0.0349 (6)	0.0009 (4)	0.0124 (5)	0.0009 (4)
C28	0.0400 (7)	0.0205 (6)	0.0478 (7)	0.0047 (5)	0.0164 (6)	−0.0001 (5)
C29	0.0293 (5)	0.0172 (5)	0.0226 (5)	0.0044 (4)	0.0060 (4)	0.0047 (4)
C30	0.0289 (5)	0.0167 (5)	0.0238 (5)	0.0044 (4)	0.0065 (4)	0.0032 (4)
C31	0.0294 (5)	0.0175 (5)	0.0246 (5)	0.0050 (4)	0.0057 (4)	0.0039 (4)
C32	0.0287 (5)	0.0167 (5)	0.0236 (5)	0.0038 (4)	0.0058 (4)	0.0025 (4)
C33	0.0322 (5)	0.0170 (5)	0.0237 (5)	0.0051 (4)	0.0065 (4)	0.0029 (4)
C34	0.0279 (5)	0.0167 (5)	0.0224 (5)	0.0038 (4)	0.0054 (4)	0.0018 (4)
C35	0.0324 (5)	0.0179 (5)	0.0225 (5)	0.0059 (4)	0.0055 (4)	0.0025 (4)
C36	0.0297 (5)	0.0173 (5)	0.0215 (5)	0.0047 (4)	0.0050 (4)	0.0019 (4)
C37	0.0344 (6)	0.0188 (5)	0.0218 (5)	0.0068 (4)	0.0061 (4)	0.0009 (4)
C38	0.0312 (5)	0.0180 (5)	0.0225 (5)	0.0052 (4)	0.0059 (4)	0.0010 (4)
C39	0.0411 (6)	0.0212 (5)	0.0225 (5)	0.0111 (5)	0.0056 (5)	0.0012 (4)
C40	0.0317 (5)	0.0195 (5)	0.0213 (5)	0.0064 (4)	0.0055 (4)	0.0004 (4)
C41	0.0453 (7)	0.0217 (5)	0.0219 (5)	0.0128 (5)	0.0043 (5)	−0.0003 (4)
C42	0.0294 (5)	0.0195 (5)	0.0233 (5)	0.0054 (4)	0.0047 (4)	−0.0015 (4)
C43	0.0394 (6)	0.0212 (5)	0.0253 (5)	0.0099 (5)	0.0022 (5)	−0.0022 (4)
C44	0.0400 (6)	0.0230 (6)	0.0343 (6)	0.0106 (5)	0.0023 (5)	−0.0056 (5)

Geometric parameters (Å, º) top

O1—C16	1.3734 (13)	C24B—H24E	0.9800
O1—C27	1.4334 (14)	C24B—H24F	0.9800
O2—C10	1.3642 (12)	C25B—C26B	1.527 (3)
O2—C29	1.4344 (12)	C25B—H25C	0.9900
N1—N2	1.2610 (12)	C25B—H25D	0.9900
N1—C1	1.4255 (13)	C26B—H26D	0.9800
N2—C7	1.4209 (13)	C26B—H26E	0.9800
C1—C6	1.4105 (14)	C26B—H26F	0.9800
C1—C2	1.4120 (14)	C27—C28	1.5114 (16)
C2—C3	1.3973 (15)	C27—H27A	0.9900
C2—C19	1.5100 (16)	C27—H27B	0.9900
C3—C4	1.3940 (15)	C28—H28A	0.9800
C3—H3	0.9500	C28—H28B	0.9800
C4—C5	1.4005 (14)	C28—H28C	0.9800
C4—C13	1.4848 (14)	C29—C30	1.5130 (15)
C5—C6	1.3908 (14)	C29—H29A	0.9900
C5—H5	0.9500	C29—H29B	0.9900
C6—C21	1.5141 (14)	C30—C31	1.5240 (14)
C7—C12	1.3836 (15)	C30—H30A	0.9900
C7—C8	1.4031 (14)	C30—H30B	0.9900
C8—C9	1.3836 (14)	C31—C32	1.5292 (15)
C8—H8	0.9500	C31—H31A	0.9900
C9—C10	1.4140 (14)	C31—H31B	0.9900
C9—C23A	1.5178 (14)	C32—C33	1.5236 (14)
C10—C11	1.3918 (14)	C32—H32A	0.9900
C11—C12	1.3892 (15)	C32—H32B	0.9900
C11—H11	0.9500	C33—C34	1.5269 (15)
C12—H12	0.9500	C33—H33A	0.9900
C13—C18	1.3926 (15)	C33—H33B	0.9900
C13—C14	1.4040 (15)	C34—C35	1.5251 (14)
C14—C15	1.3837 (15)	C34—H34A	0.9900
C14—H14	0.9500	C34—H34B	0.9900
C15—C16	1.3939 (16)	C35—C36	1.5276 (15)
C15—H15	0.9500	C35—H35A	0.9900
C16—C17	1.3906 (15)	C35—H35B	0.9900
C17—C18	1.3936 (15)	C36—C37	1.5241 (14)
C17—H17	0.9500	C36—H36A	0.9900
C18—H18	0.9500	C36—H36B	0.9900
C19—C20	1.525 (2)	C37—C38	1.5297 (15)
C19—H19A	0.9900	C37—H37A	0.9900
C19—H19B	0.9900	C37—H37B	0.9900
C20—H20A	0.9800	C38—C39	1.5221 (15)
C20—H20B	0.9800	C38—H38A	0.9900
C20—H20C	0.9800	C38—H38B	0.9900
C21—C22	1.5282 (16)	C39—C40	1.5270 (15)
C21—H21A	0.9900	C39—H39A	0.9900
C21—H21B	0.9900	C39—H39B	0.9900
C22—H22A	0.9800	C40—C41	1.5245 (15)
C22—H22B	0.9800	C40—H40A	0.9900
C22—H22C	0.9800	C40—H40B	0.9900
C23A—C25A	1.524 (3)	C41—C42	1.5224 (15)
C23A—C24A	1.540 (2)	C41—H41A	0.9900
C23A—H23A	1.0000	C41—H41B	0.9900
C24A—H24A	0.9800	C42—C43	1.5240 (15)
C24A—H24B	0.9800	C42—H42A	0.9900
C24A—H24C	0.9800	C42—H42B	0.9900
C25A—C26A	1.522 (2)	C43—C44	1.5256 (16)
C25A—H25A	0.9900	C43—H43A	0.9900
C25A—H25B	0.9900	C43—H43B	0.9900
C26A—H26A	0.9800	C44—H44A	0.9800
C26A—H26B	0.9800	C44—H44B	0.9800
C26A—H26C	0.9800	C44—H44C	0.9800
C24B—H24D	0.9800

C16—O1—C27	117.47 (8)	C28—C27—H27B	110.2
C10—O2—C29	118.82 (8)	H27A—C27—H27B	108.5
N2—N1—C1	115.39 (8)	C27—C28—H28A	109.5
N1—N2—C7	114.11 (8)	C27—C28—H28B	109.5
C6—C1—C2	120.64 (9)	H28A—C28—H28B	109.5
C6—C1—N1	113.48 (9)	C27—C28—H28C	109.5
C2—C1—N1	125.85 (9)	H28A—C28—H28C	109.5
C3—C2—C1	117.73 (10)	H28B—C28—H28C	109.5
C3—C2—C19	117.18 (10)	O2—C29—C30	106.28 (8)
C1—C2—C19	125.06 (10)	O2—C29—H29A	110.5
C4—C3—C2	123.09 (10)	C30—C29—H29A	110.5
C4—C3—H3	118.5	O2—C29—H29B	110.5
C2—C3—H3	118.5	C30—C29—H29B	110.5
C3—C4—C5	117.55 (10)	H29A—C29—H29B	108.7
C3—C4—C13	120.98 (9)	C29—C30—C31	113.31 (9)
C5—C4—C13	121.46 (10)	C29—C30—H30A	108.9
C6—C5—C4	121.91 (10)	C31—C30—H30A	108.9
C6—C5—H5	119.0	C29—C30—H30B	108.9
C4—C5—H5	119.0	C31—C30—H30B	108.9
C5—C6—C1	119.06 (9)	H30A—C30—H30B	107.7
C5—C6—C21	119.73 (9)	C30—C31—C32	111.16 (9)
C1—C6—C21	121.16 (9)	C30—C31—H31A	109.4
C12—C7—C8	119.78 (9)	C32—C31—H31A	109.4
C12—C7—N2	116.01 (9)	C30—C31—H31B	109.4
C8—C7—N2	124.15 (9)	C32—C31—H31B	109.4
C9—C8—C7	121.17 (9)	H31A—C31—H31B	108.0
C9—C8—H8	119.4	C33—C32—C31	114.35 (9)
C7—C8—H8	119.4	C33—C32—H32A	108.7
C8—C9—C10	117.99 (9)	C31—C32—H32A	108.7
C8—C9—C23A	122.71 (9)	C33—C32—H32B	108.7
C10—C9—C23A	119.23 (9)	C31—C32—H32B	108.7
O2—C10—C11	123.86 (9)	H32A—C32—H32B	107.6
O2—C10—C9	114.97 (9)	C32—C33—C34	112.51 (9)
C11—C10—C9	121.16 (9)	C32—C33—H33A	109.1
C12—C11—C10	119.45 (9)	C34—C33—H33A	109.1
C12—C11—H11	120.3	C32—C33—H33B	109.1
C10—C11—H11	120.3	C34—C33—H33B	109.1
C7—C12—C11	120.41 (10)	H33A—C33—H33B	107.8
C7—C12—H12	119.8	C35—C34—C33	113.77 (9)
C11—C12—H12	119.8	C35—C34—H34A	108.8
C18—C13—C14	117.53 (10)	C33—C34—H34A	108.8
C18—C13—C4	121.28 (9)	C35—C34—H34B	108.8
C14—C13—C4	121.19 (10)	C33—C34—H34B	108.8
C15—C14—C13	121.48 (10)	H34A—C34—H34B	107.7
C15—C14—H14	119.3	C34—C35—C36	113.05 (9)
C13—C14—H14	119.3	C34—C35—H35A	109.0
C14—C15—C16	119.88 (10)	C36—C35—H35A	109.0
C14—C15—H15	120.1	C34—C35—H35B	109.0
C16—C15—H15	120.1	C36—C35—H35B	109.0
O1—C16—C17	124.16 (10)	H35A—C35—H35B	107.8
O1—C16—C15	115.97 (9)	C37—C36—C35	113.61 (9)
C17—C16—C15	119.87 (10)	C37—C36—H36A	108.8
C16—C17—C18	119.49 (10)	C35—C36—H36A	108.8
C16—C17—H17	120.3	C37—C36—H36B	108.8
C18—C17—H17	120.3	C35—C36—H36B	108.8
C13—C18—C17	121.76 (10)	H36A—C36—H36B	107.7
C13—C18—H18	119.1	C36—C37—C38	113.43 (9)
C17—C18—H18	119.1	C36—C37—H37A	108.9
C2—C19—C20	113.25 (12)	C38—C37—H37A	108.9
C2—C19—H19A	108.9	C36—C37—H37B	108.9
C20—C19—H19A	108.9	C38—C37—H37B	108.9
C2—C19—H19B	108.9	H37A—C37—H37B	107.7
C20—C19—H19B	108.9	C39—C38—C37	113.36 (9)
H19A—C19—H19B	107.7	C39—C38—H38A	108.9
C19—C20—H20A	109.5	C37—C38—H38A	108.9
C19—C20—H20B	109.5	C39—C38—H38B	108.9
H20A—C20—H20B	109.5	C37—C38—H38B	108.9
C19—C20—H20C	109.5	H38A—C38—H38B	107.7
H20A—C20—H20C	109.5	C38—C39—C40	113.43 (9)
H20B—C20—H20C	109.5	C38—C39—H39A	108.9
C6—C21—C22	113.29 (9)	C40—C39—H39A	108.9
C6—C21—H21A	108.9	C38—C39—H39B	108.9
C22—C21—H21A	108.9	C40—C39—H39B	108.9
C6—C21—H21B	108.9	H39A—C39—H39B	107.7
C22—C21—H21B	108.9	C41—C40—C39	113.49 (9)
H21A—C21—H21B	107.7	C41—C40—H40A	108.9
C21—C22—H22A	109.5	C39—C40—H40A	108.9
C21—C22—H22B	109.5	C41—C40—H40B	108.9
H22A—C22—H22B	109.5	C39—C40—H40B	108.9
C21—C22—H22C	109.5	H40A—C40—H40B	107.7
H22A—C22—H22C	109.5	C42—C41—C40	113.59 (9)
H22B—C22—H22C	109.5	C42—C41—H41A	108.8
C9—C23A—C25A	109.44 (13)	C40—C41—H41A	108.8
C9—C23A—C24A	112.11 (11)	C42—C41—H41B	108.8
C25A—C23A—C24A	112.13 (13)	C40—C41—H41B	108.8
C9—C23A—H23A	107.6	H41A—C41—H41B	107.7
C25A—C23A—H23A	107.6	C41—C42—C43	113.28 (9)
C24A—C23A—H23A	107.6	C41—C42—H42A	108.9
C26A—C25A—C23A	113.7 (2)	C43—C42—H42A	108.9
H24D—C24B—H24E	109.5	C41—C42—H42B	108.9
H24D—C24B—H24F	109.5	C43—C42—H42B	108.9
H24E—C24B—H24F	109.5	H42A—C42—H42B	107.7
C26B—C25B—H25C	109.0	C42—C43—C44	112.99 (10)
C26B—C25B—H25D	109.0	C42—C43—H43A	109.0
H25C—C25B—H25D	107.8	C44—C43—H43A	109.0
C25B—C26B—H26D	109.5	C42—C43—H43B	109.0
C25B—C26B—H26E	109.5	C44—C43—H43B	109.0
H26D—C26B—H26E	109.5	H43A—C43—H43B	107.8
C25B—C26B—H26F	109.5	C43—C44—H44A	109.5
H26D—C26B—H26F	109.5	C43—C44—H44B	109.5
H26E—C26B—H26F	109.5	H44A—C44—H44B	109.5
O1—C27—C28	107.34 (9)	C43—C44—H44C	109.5
O1—C27—H27A	110.2	H44A—C44—H44C	109.5
C28—C27—H27A	110.2	H44B—C44—H44C	109.5
O1—C27—H27B	110.2

C1—N1—N2—C7	−178.05 (8)	C5—C4—C13—C14	−148.69 (11)
N2—N1—C1—C6	156.32 (9)	C18—C13—C14—C15	0.01 (16)
N2—N1—C1—C2	−26.08 (15)	C4—C13—C14—C15	−179.13 (10)
C6—C1—C2—C3	−0.63 (16)	C13—C14—C15—C16	−0.26 (17)
N1—C1—C2—C3	−178.08 (10)	C27—O1—C16—C17	12.25 (16)
C6—C1—C2—C19	177.20 (12)	C27—O1—C16—C15	−168.18 (10)
N1—C1—C2—C19	−0.25 (19)	C14—C15—C16—O1	−179.43 (10)
C1—C2—C3—C4	−0.68 (17)	C14—C15—C16—C17	0.16 (17)
C19—C2—C3—C4	−178.67 (12)	O1—C16—C17—C18	179.73 (10)
C2—C3—C4—C5	0.94 (17)	C15—C16—C17—C18	0.18 (17)
C2—C3—C4—C13	179.90 (10)	C14—C13—C18—C17	0.34 (16)
C3—C4—C5—C6	0.12 (16)	C4—C13—C18—C17	179.48 (10)
C13—C4—C5—C6	−178.84 (10)	C16—C17—C18—C13	−0.43 (17)
C4—C5—C6—C1	−1.37 (16)	C3—C2—C19—C20	−90.18 (14)
C4—C5—C6—C21	−178.86 (10)	C1—C2—C19—C20	91.98 (15)
C2—C1—C6—C5	1.62 (16)	C5—C6—C21—C22	108.44 (11)
N1—C1—C6—C5	179.37 (9)	C1—C6—C21—C22	−68.99 (13)
C2—C1—C6—C21	179.07 (10)	C8—C9—C23A—C25A	92.27 (15)
N1—C1—C6—C21	−3.18 (14)	C10—C9—C23A—C25A	−84.89 (14)
N1—N2—C7—C12	−171.40 (10)	C8—C9—C23A—C24A	−32.80 (16)
N1—N2—C7—C8	11.61 (15)	C10—C9—C23A—C24A	150.04 (13)
C12—C7—C8—C9	0.19 (16)	C9—C23A—C25A—C26A	168.18 (15)
N2—C7—C8—C9	177.07 (9)	C24A—C23A—C25A—C26A	−66.8 (2)
C7—C8—C9—C10	1.11 (15)	C16—O1—C27—C28	174.10 (10)
C7—C8—C9—C23A	−176.08 (10)	C10—O2—C29—C30	−177.81 (9)
C29—O2—C10—C11	2.10 (15)	O2—C29—C30—C31	−176.92 (9)
C29—O2—C10—C9	−178.00 (9)	C29—C30—C31—C32	178.85 (9)
C8—C9—C10—O2	179.21 (9)	C30—C31—C32—C33	178.70 (9)
C23A—C9—C10—O2	−3.50 (14)	C31—C32—C33—C34	178.96 (9)
C8—C9—C10—C11	−0.89 (15)	C32—C33—C34—C35	−179.62 (9)
C23A—C9—C10—C11	176.41 (10)	C33—C34—C35—C36	−179.13 (9)
O2—C10—C11—C12	179.25 (10)	C34—C35—C36—C37	−175.90 (9)
C9—C10—C11—C12	−0.65 (16)	C35—C36—C37—C38	−179.93 (10)
C8—C7—C12—C11	−1.77 (16)	C36—C37—C38—C39	178.76 (10)
N2—C7—C12—C11	−178.90 (10)	C37—C38—C39—C40	−178.43 (10)
C10—C11—C12—C7	1.99 (16)	C38—C39—C40—C41	179.06 (10)
C3—C4—C13—C18	−146.73 (11)	C39—C40—C41—C42	179.56 (10)
C5—C4—C13—C18	32.19 (15)	C40—C41—C42—C43	177.41 (10)
C3—C4—C13—C14	32.38 (16)	C41—C42—C43—C44	−178.70 (11)

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1-[(E)-3-sec-Butyl-4-(4′-eth­oxy-3,5-diethyl­biphenyl-4-yldiazen­yl)phen­oxy]hexa­deca­ne

Supporting information

Key indicators

checkCIF/PLATON results

1-[(E)-3-sec-Butyl-4-(4′-ethoxy-3,5-diethylbiphenyl-4-yldiazenyl)phenoxy]hexadecane