(Z)-N-tert-Butyl-2-(4-meth­oxy­anilino)-N′-(4-meth­oxy­phen­yl)-2-phenyl­acetimidamide

Roberts, S.A.; Saha, B.; Frett, B.; Li, H.-Y.

doi:10.1107/S1600536813012877

(Z)-N-tert-Butyl-2-(4-methoxyanilino)-N′-(4-methoxyphenyl)-2-phenylacetimidamide

S. A. Roberts, B. Saha, B. Frett and H.-Y. Li

In the crystal of the title compound, C₂₆H₃₁N₃O₂, pairs of N—H

O hydrogen bonds link molecules, forming inversion dimers, which enclose an R₂²(20) ring motif. One N atom does not form hydrogen bonds and lies in a hydrophobic pocket with closest intermolecular contacts of 4.196 (2) and 4.262 (2) Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536813012877/pk2477sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536813012877/pk2477Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536813012877/pk2477Isup3.cml Supplementary material

CCDC reference: 955050

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.043
wR factor = 0.106
Data-to-parameter ratio = 22.9

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ?
PLAT007_ALERT_5_G Note: Number of Unrefined Donor-H Atoms ........          1
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00400 Deg.
PLAT793_ALERT_4_G The Model has Chirality at C1      (Verify) ....          R
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         61

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

The title compound was prepared as a secondary product of the three component Ugi reaction (Saha et al., 2013). The central C1—C22 single bond has four bulky substituents arranged, roughly, as if pointing at the corners of a tetrahedron. The angle between the planes containing the substituents, defined by N1—C22—N3 and C2—C1—C20, is 72.41 (1)°. Pairs of hydrogen bonds between N2 and O1 [3.170 (1) Å] connect two molecules across an inversion center, creating a cavity around the inversion center with a diameter of about 5 Å. The closest contact across the inversion center involving atoms not involved in the hydrogen bonding is 3.151 (3) Å between the hydrogen bonded to C3 and its symmetry equivalent (symmetry transformation -x + 1, -y + 2, -z + 2). The hydrogen bonding graph set is R²₂(20). Nitrogen N3 is unusual in that, although protonated, it does not form hydrogen bonds with acceptor atoms. Instead, it lies in a hydrophobic cavity with closest intermolecular contacts of 4.196 (2) Å and 4.262 (2) Å to C15 and C16 respectively.

Related literature top

For the synthesis of the title compound, and a discussion of the use of the three-component Ugi reaction to synthesize amidines, see: Saha et al. (2013)

Experimental top

The compound was synthesized as previously reported [compound 5a in (Saha et al., 2013)]. The crude residue was purified by silica gel column chromatography using (10–30%) ethylacetate-hexane to obtain the pure product. The pure compound was dissolved in 50% ethylacetate-hexane and kept at room temperature for 2 days during which crystals formed.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound. Non-hydrogen atoms are shown as 50% probability ellipsoids.
	Fig. 2. View showing unit cell packing. Unit cell axes are labeled in the figure.

(Z)-N-tert-Butyl-2-(4-methoxyanilino)-N'-(4-methoxyphenyl)-2-phenylacetimidamide top

Crystal data top

C₂₆H₃₁N₃O₂	Z = 2
M_r = 417.54	F(000) = 448
Triclinic, P1	D_x = 1.199 Mg m⁻³
a = 10.0804 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5784 (17) Å	Cell parameters from 9952 reflections
c = 11.1573 (18) Å	θ = 2.9–29.8°
α = 80.982 (4)°	µ = 0.08 mm⁻¹
β = 85.152 (4)°	T = 100 K
γ = 80.270 (4)°	Block, colourless
V = 1156.1 (3) Å³	0.20 × 0.20 × 0.10 mm

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	6607 independent reflections
Radiation source: fine-focus sealed tube	5476 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 8.3333 pixels mm^-1	θ_max = 29.9°, θ_min = 1.9°
ϕ and ω scans	h = −14→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→12
T_min = 0.89, T_max = 0.99	l = −15→13
32612 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ²(F_o²) + (0.0397P)² + 0.6486P] where P = (F_o² + 2F_c²)/3
6607 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₆H₃₁N₃O₂	γ = 80.270 (4)°
M_r = 417.54	V = 1156.1 (3) Å³
Triclinic, P1	Z = 2
a = 10.0804 (17) Å	Mo Kα radiation
b = 10.5784 (17) Å	µ = 0.08 mm⁻¹
c = 11.1573 (18) Å	T = 100 K
α = 80.982 (4)°	0.20 × 0.20 × 0.10 mm
β = 85.152 (4)°

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	6607 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5476 reflections with I > 2σ(I)
T_min = 0.89, T_max = 0.99	R_int = 0.019
32612 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.36 e Å⁻³
6607 reflections	Δρ_min = −0.38 e Å⁻³
289 parameters

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
C20	0.37947 (10)	1.03405 (9)	0.68022 (9)	0.01884 (19)
C11	0.15660 (10)	0.92039 (10)	1.16518 (9)	0.0213 (2)
H11	0.0822	0.9836	1.1842	0.026*
C18	0.15655 (11)	1.15884 (10)	0.70473 (10)	0.0226 (2)
H18	0.0708	1.1695	0.7475	0.027*
C15	0.40664 (11)	1.12635 (10)	0.57996 (9)	0.02047 (19)
H15	0.4919	1.1155	0.5363	0.025*
C16	0.31125 (11)	1.23257 (10)	0.54406 (9)	0.0219 (2)
H16	0.3313	1.2940	0.4761	0.026*
C22	0.35777 (10)	0.75795 (9)	0.82814 (9)	0.01868 (19)
C10	0.36795 (11)	0.78673 (11)	1.21611 (9)	0.0228 (2)
H10	0.4377	0.7582	1.2709	0.027*
C12	0.16277 (10)	0.86653 (10)	1.05826 (9)	0.0212 (2)
H12	0.0906	0.8921	1.0057	0.025*
C19	0.25281 (11)	1.05135 (10)	0.74063 (10)	0.0224 (2)
H19	0.2315	0.9890	0.8074	0.027*
C8	0.27219 (10)	0.77613 (10)	1.02648 (9)	0.01957 (19)
C1	0.46163 (10)	0.84821 (9)	0.83240 (9)	0.01839 (18)
H1	0.4260	0.9082	0.8927	0.022*
C17	0.18548 (10)	1.25005 (10)	0.60709 (9)	0.0206 (2)
C9	0.37371 (11)	0.73460 (10)	1.10887 (9)	0.0223 (2)
H9	0.4473	0.6700	1.0910	0.027*
C2	0.59808 (10)	0.77504 (10)	0.87123 (9)	0.0209 (2)
C26	0.27437 (11)	0.63246 (10)	0.68176 (9)	0.0220 (2)
C3	0.67295 (12)	0.83256 (11)	0.93977 (11)	0.0280 (2)
H3	0.6367	0.9144	0.9636	0.034*
C24	0.12887 (12)	0.70234 (13)	0.67994 (12)	0.0318 (3)
H24A	0.0962	0.7183	0.7623	0.048*
H24B	0.0722	0.6484	0.6505	0.048*
H24C	0.1249	0.7852	0.6258	0.048*
C7	0.65156 (13)	0.65363 (12)	0.83952 (12)	0.0329 (3)
H7	0.6010	0.6121	0.7938	0.039*
C25	0.32629 (13)	0.61040 (12)	0.55297 (10)	0.0299 (2)
H25A	0.3167	0.6936	0.4991	0.045*
H25B	0.2739	0.5524	0.5239	0.045*
H25C	0.4215	0.5710	0.5532	0.045*
C4	0.80027 (13)	0.77209 (13)	0.97403 (12)	0.0336 (3)
H4	0.8505	0.8127	1.0209	0.040*
C21	−0.02644 (12)	1.38154 (12)	0.63778 (12)	0.0333 (3)
H21A	−0.0784	1.3119	0.6344	0.050*
H21B	−0.0785	1.4649	0.6052	0.050*
H21C	−0.0078	1.3829	0.7223	0.050*
C14	0.15403 (12)	1.02124 (13)	1.38420 (12)	0.0335 (3)
H14A	0.1460	1.0989	1.3229	0.050*
H14B	0.1674	1.0449	1.4633	0.050*
H14C	0.0715	0.9827	1.3897	0.050*
C5	0.85386 (12)	0.65322 (13)	0.94015 (12)	0.0350 (3)
H5	0.9419	0.6128	0.9616	0.042*
C23	0.28606 (16)	0.50314 (12)	0.76560 (12)	0.0366 (3)
H23A	0.3800	0.4597	0.7629	0.055*
H23B	0.2285	0.4483	0.7388	0.055*
H23C	0.2573	0.5183	0.8490	0.055*
C6	0.77862 (14)	0.59305 (14)	0.87460 (13)	0.0405 (3)
H6	0.8141	0.5098	0.8535	0.049*
O2	0.09729 (8)	1.35968 (7)	0.56724 (7)	0.02582 (17)
O1	0.26631 (8)	0.92977 (8)	1.35034 (7)	0.02582 (17)
N2	0.47953 (9)	0.92663 (8)	0.71356 (8)	0.01953 (17)
N3	0.36308 (9)	0.71424 (9)	0.71966 (8)	0.02124 (18)
H3A	0.4268	0.7374	0.6658	0.025*
N1	0.27336 (9)	0.72595 (9)	0.91628 (8)	0.02123 (18)
C13	0.26038 (10)	0.88065 (10)	1.24380 (9)	0.0204 (2)
H2	0.5625 (15)	0.9449 (14)	0.6977 (13)	0.027 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C20	0.0210 (4)	0.0187 (4)	0.0171 (4)	−0.0043 (4)	−0.0002 (3)	−0.0025 (3)
C11	0.0189 (4)	0.0221 (5)	0.0226 (5)	−0.0038 (4)	0.0033 (4)	−0.0041 (4)
C18	0.0203 (5)	0.0226 (5)	0.0236 (5)	−0.0037 (4)	0.0019 (4)	−0.0008 (4)
C15	0.0230 (5)	0.0221 (5)	0.0164 (4)	−0.0057 (4)	0.0020 (4)	−0.0025 (3)
C16	0.0275 (5)	0.0212 (5)	0.0168 (4)	−0.0066 (4)	0.0000 (4)	0.0002 (3)
C22	0.0206 (4)	0.0177 (4)	0.0170 (4)	−0.0019 (3)	−0.0004 (3)	−0.0022 (3)
C10	0.0227 (5)	0.0274 (5)	0.0177 (4)	−0.0019 (4)	−0.0007 (4)	−0.0033 (4)
C12	0.0198 (4)	0.0246 (5)	0.0191 (4)	−0.0052 (4)	0.0003 (4)	−0.0017 (4)
C19	0.0229 (5)	0.0210 (5)	0.0212 (5)	−0.0034 (4)	0.0025 (4)	0.0016 (4)
C8	0.0219 (5)	0.0212 (5)	0.0160 (4)	−0.0072 (4)	0.0026 (4)	−0.0018 (3)
C1	0.0202 (4)	0.0185 (4)	0.0160 (4)	−0.0032 (3)	0.0014 (3)	−0.0021 (3)
C17	0.0228 (5)	0.0189 (5)	0.0205 (4)	−0.0036 (4)	−0.0036 (4)	−0.0022 (4)
C9	0.0231 (5)	0.0236 (5)	0.0186 (4)	−0.0005 (4)	0.0014 (4)	−0.0035 (4)
C2	0.0204 (4)	0.0227 (5)	0.0176 (4)	−0.0023 (4)	0.0017 (4)	0.0003 (4)
C26	0.0253 (5)	0.0227 (5)	0.0190 (4)	−0.0051 (4)	−0.0019 (4)	−0.0050 (4)
C3	0.0265 (5)	0.0246 (5)	0.0331 (6)	−0.0050 (4)	−0.0047 (4)	−0.0024 (4)
C24	0.0237 (5)	0.0407 (7)	0.0322 (6)	−0.0036 (5)	−0.0011 (4)	−0.0112 (5)
C7	0.0319 (6)	0.0317 (6)	0.0344 (6)	0.0050 (5)	−0.0052 (5)	−0.0120 (5)
C25	0.0323 (6)	0.0362 (6)	0.0235 (5)	−0.0045 (5)	−0.0005 (4)	−0.0132 (4)
C4	0.0283 (6)	0.0347 (6)	0.0371 (6)	−0.0080 (5)	−0.0088 (5)	0.0036 (5)
C21	0.0233 (5)	0.0299 (6)	0.0406 (7)	0.0017 (4)	−0.0003 (5)	0.0062 (5)
C14	0.0255 (5)	0.0433 (7)	0.0359 (6)	−0.0052 (5)	0.0066 (5)	−0.0234 (5)
C5	0.0249 (5)	0.0396 (7)	0.0336 (6)	0.0028 (5)	−0.0021 (5)	0.0080 (5)
C23	0.0594 (8)	0.0243 (6)	0.0291 (6)	−0.0136 (6)	−0.0126 (6)	−0.0005 (4)
C6	0.0363 (7)	0.0366 (7)	0.0433 (7)	0.0128 (5)	−0.0028 (6)	−0.0091 (6)
O2	0.0252 (4)	0.0223 (4)	0.0267 (4)	−0.0005 (3)	−0.0026 (3)	0.0034 (3)
O1	0.0240 (4)	0.0337 (4)	0.0215 (4)	−0.0035 (3)	0.0026 (3)	−0.0124 (3)
N2	0.0194 (4)	0.0206 (4)	0.0172 (4)	−0.0035 (3)	0.0028 (3)	−0.0002 (3)
N3	0.0237 (4)	0.0240 (4)	0.0171 (4)	−0.0065 (3)	0.0030 (3)	−0.0056 (3)
N1	0.0246 (4)	0.0233 (4)	0.0164 (4)	−0.0062 (3)	0.0010 (3)	−0.0033 (3)
C13	0.0213 (5)	0.0235 (5)	0.0173 (4)	−0.0069 (4)	0.0035 (4)	−0.0047 (4)

Geometric parameters (Å, º) top

C20—C15	1.4057 (14)	C26—C25	1.5264 (15)
C20—C19	1.3901 (14)	C26—C23	1.5243 (16)
C20—N2	1.4108 (13)	C26—N3	1.4721 (13)
C11—H11	0.9500	C3—H3	0.9500
C11—C12	1.3930 (14)	C3—C4	1.3897 (17)
C11—C13	1.3897 (15)	C24—H24A	0.9800
C18—H18	0.9500	C24—H24B	0.9800
C18—C19	1.3946 (15)	C24—H24C	0.9800
C18—C17	1.3836 (14)	C7—H7	0.9500
C15—H15	0.9500	C7—C6	1.3903 (18)
C15—C16	1.3807 (15)	C25—H25A	0.9800
C16—H16	0.9500	C25—H25B	0.9800
C16—C17	1.3953 (15)	C25—H25C	0.9800
C22—C1	1.5397 (14)	C4—H4	0.9500
C22—N3	1.3556 (12)	C4—C5	1.3787 (19)
C22—N1	1.2873 (13)	C21—H21A	0.9800
C10—H10	0.9500	C21—H21B	0.9800
C10—C9	1.3869 (14)	C21—H21C	0.9800
C10—C13	1.3906 (15)	C21—O2	1.4220 (15)
C12—H12	0.9500	C14—H14A	0.9800
C12—C8	1.3930 (15)	C14—H14B	0.9800
C19—H19	0.9500	C14—H14C	0.9800
C8—C9	1.4021 (14)	C14—O1	1.4256 (14)
C8—N1	1.4120 (13)	C5—H5	0.9500
C1—H1	1.0000	C5—C6	1.385 (2)
C1—C2	1.5213 (14)	C23—H23A	0.9800
C1—N2	1.4643 (13)	C23—H23B	0.9800
C17—O2	1.3747 (12)	C23—H23C	0.9800
C9—H9	0.9500	C6—H6	0.9500
C2—C3	1.3868 (15)	O1—C13	1.3794 (12)
C2—C7	1.3934 (16)	N2—H2	0.887 (15)
C26—C24	1.5270 (16)	N3—H3A	0.8800

C15—C20—N2	119.16 (9)	C26—C24—H24A	109.5
C19—C20—C15	118.08 (9)	C26—C24—H24B	109.5
C19—C20—N2	122.74 (9)	C26—C24—H24C	109.5
C12—C11—H11	120.3	H24A—C24—H24B	109.5
C13—C11—H11	120.3	H24A—C24—H24C	109.5
C13—C11—C12	119.31 (9)	H24B—C24—H24C	109.5
C19—C18—H18	119.9	C2—C7—H7	119.9
C17—C18—H18	119.9	C6—C7—C2	120.22 (12)
C17—C18—C19	120.28 (10)	C6—C7—H7	119.9
C20—C15—H15	119.5	C26—C25—H25A	109.5
C16—C15—C20	120.96 (10)	C26—C25—H25B	109.5
C16—C15—H15	119.5	C26—C25—H25C	109.5
C15—C16—H16	119.8	H25A—C25—H25B	109.5
C15—C16—C17	120.31 (9)	H25A—C25—H25C	109.5
C17—C16—H16	119.8	H25B—C25—H25C	109.5
N3—C22—C1	112.76 (8)	C3—C4—H4	119.9
N1—C22—C1	124.98 (9)	C5—C4—C3	120.11 (12)
N1—C22—N3	122.26 (9)	C5—C4—H4	119.9
C9—C10—H10	119.9	H21A—C21—H21B	109.5
C9—C10—C13	120.25 (10)	H21A—C21—H21C	109.5
C13—C10—H10	119.9	H21B—C21—H21C	109.5
C11—C12—H12	119.2	O2—C21—H21A	109.5
C11—C12—C8	121.63 (10)	O2—C21—H21B	109.5
C8—C12—H12	119.2	O2—C21—H21C	109.5
C20—C19—C18	120.99 (9)	H14A—C14—H14B	109.5
C20—C19—H19	119.5	H14A—C14—H14C	109.5
C18—C19—H19	119.5	H14B—C14—H14C	109.5
C12—C8—C9	118.01 (9)	O1—C14—H14A	109.5
C12—C8—N1	119.03 (9)	O1—C14—H14B	109.5
C9—C8—N1	122.89 (9)	O1—C14—H14C	109.5
C22—C1—H1	108.1	C4—C5—H5	120.2
C2—C1—C22	112.85 (8)	C4—C5—C6	119.59 (11)
C2—C1—H1	108.1	C6—C5—H5	120.2
N2—C1—C22	110.37 (8)	C26—C23—H23A	109.5
N2—C1—H1	108.1	C26—C23—H23B	109.5
N2—C1—C2	109.12 (8)	C26—C23—H23C	109.5
C18—C17—C16	119.35 (9)	H23A—C23—H23B	109.5
O2—C17—C18	123.94 (10)	H23A—C23—H23C	109.5
O2—C17—C16	116.71 (9)	H23B—C23—H23C	109.5
C10—C9—C8	120.74 (10)	C7—C6—H6	119.8
C10—C9—H9	119.6	C5—C6—C7	120.43 (12)
C8—C9—H9	119.6	C5—C6—H6	119.8
C3—C2—C1	118.49 (9)	C17—O2—C21	116.18 (8)
C3—C2—C7	118.73 (10)	C13—O1—C14	117.04 (9)
C7—C2—C1	122.78 (10)	C20—N2—C1	118.01 (8)
C25—C26—C24	109.45 (9)	C20—N2—H2	112.8 (9)
C23—C26—C24	111.49 (10)	C1—N2—H2	113.0 (9)
C23—C26—C25	109.80 (10)	C22—N3—C26	127.34 (9)
N3—C26—C24	110.61 (9)	C22—N3—H3A	116.3
N3—C26—C25	105.50 (9)	C26—N3—H3A	116.3
N3—C26—C23	109.82 (9)	C22—N1—C8	119.35 (9)
C2—C3—H3	119.6	C11—C13—C10	119.96 (9)
C2—C3—C4	120.89 (11)	O1—C13—C11	124.18 (9)
C4—C3—H3	119.6	O1—C13—C10	115.85 (9)

C20—C15—C16—C17	−0.05 (16)	C9—C8—N1—C22	−72.76 (14)
C11—C12—C8—C9	3.56 (15)	C2—C1—N2—C20	−157.97 (9)
C11—C12—C8—N1	−179.35 (9)	C2—C3—C4—C5	−0.11 (19)
C18—C17—O2—C21	4.27 (15)	C2—C7—C6—C5	−0.7 (2)
C15—C20—C19—C18	−1.56 (16)	C3—C2—C7—C6	−1.07 (19)
C15—C20—N2—C1	166.59 (9)	C3—C4—C5—C6	−1.7 (2)
C15—C16—C17—C18	−1.01 (16)	C24—C26—N3—C22	62.76 (14)
C15—C16—C17—O2	178.62 (9)	C7—C2—C3—C4	1.49 (17)
C16—C17—O2—C21	−175.34 (10)	C25—C26—N3—C22	−178.98 (10)
C22—C1—C2—C3	−145.84 (10)	C4—C5—C6—C7	2.1 (2)
C22—C1—C2—C7	35.00 (14)	C14—O1—C13—C11	3.97 (15)
C22—C1—N2—C20	77.49 (11)	C14—O1—C13—C10	−176.82 (10)
C12—C11—C13—C10	−0.89 (15)	C23—C26—N3—C22	−60.72 (14)
C12—C11—C13—O1	178.29 (9)	N2—C20—C15—C16	179.73 (9)
C12—C8—C9—C10	−2.92 (15)	N2—C20—C19—C18	−179.91 (10)
C12—C8—N1—C22	110.29 (12)	N2—C1—C2—C3	91.07 (11)
C19—C20—C15—C16	1.32 (15)	N2—C1—C2—C7	−88.08 (12)
C19—C20—N2—C1	−15.07 (14)	N3—C22—C1—C2	−87.41 (10)
C19—C18—C17—C16	0.77 (16)	N3—C22—C1—N2	34.97 (11)
C19—C18—C17—O2	−178.83 (10)	N3—C22—N1—C8	−179.30 (9)
C1—C22—N3—C26	−176.49 (9)	N1—C22—C1—C2	92.83 (12)
C1—C22—N1—C8	0.44 (15)	N1—C22—C1—N2	−144.79 (10)
C1—C2—C3—C4	−177.70 (10)	N1—C22—N3—C26	3.28 (16)
C1—C2—C7—C6	178.08 (11)	N1—C8—C9—C10	−179.89 (10)
C17—C18—C19—C20	0.53 (16)	C13—C11—C12—C8	−1.69 (15)
C9—C10—C13—C11	1.50 (16)	C13—C10—C9—C8	0.45 (16)
C9—C10—C13—O1	−177.75 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.887 (15)	2.328 (15)	3.1698 (13)	158.5 (12)

Symmetry code: (i) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₆H₃₁N₃O₂
M_r	417.54
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.0804 (17), 10.5784 (17), 11.1573 (18)
α, β, γ (°)	80.982 (4), 85.152 (4), 80.270 (4)
V (Å³)	1156.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.89, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	32612, 6607, 5476
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.701

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.106, 0.94
No. of reflections	6607
No. of parameters	289
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.38

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).