2,4-Di-tert-butyl-6-({[2-(di­methyl­amino)­eth­yl](2-hy­droxy­benz­yl)amino}­meth­yl)phenol

Spaleniak, G.P.; Bisz, E.; Białek, M.; Zarychta, B.

doi:10.1107/S1600536814010241

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page o678

doi:10.1107/S1600536814010241

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2,4-Di-tert-butyl-6-({[2-(dimethylamino)ethyl](2-hydroxybenzyl)amino}methyl)phenol

Grzegorz P. Spaleniak,^a Elwira Bisz,^a Marzena Białek ^a and Bartosz Zarychta ^a ^*

^aFaculty of Chemistry, University of Opole, Oleska 48, 45-052 Opole, Poland
^*Correspondence e-mail: bzarychta@uni.opole.pl

Edited by M. Bolte, Goethe-Universität Frankfurt Germany (Received 5 May 2014; accepted 6 May 2014; online 17 May 2014)

The title compound, C₂₆H₄₀N₂O₂, has both its N atoms in trigonal-pyramidal geometries. The molecular structure is stabilized by O—H⋯N and C—H⋯O hydrogen bonds. In the crystal, C—H⋯π interactions lead to the formation of a supramolecular helical chain along the b-axis direction.

CCDC reference: 1001222

Related literature

For general background to the use of diaminebis(aryloxido) compounds as tetradentate ligands, see: Hirotsu et al. (1997 , 1998 ); Dutta et al. (2011 ). For related structures, see: Abrahams et al. (2009 ); Maity et al. (2006 ); Janas et al. (2012 ).

Experimental

Crystal data

C₂₆H₄₀N₂O₂
M_r = 412.60
Monoclinic, P 2₁ /c
a = 12.3002 (7) Å
b = 13.3758 (7) Å
c = 15.5662 (9) Å
β = 96.377 (5)°
V = 2545.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 150 K
0.40 × 0.37 × 0.35 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
17015 measured reflections
4964 independent reflections
2292 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.099
S = 0.78
4964 reflections
277 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.96 (2)	2.59 (2)	3.1610 (19)	118.5 (16)
O1—H1A⋯N2	0.96 (2)	1.89 (2)	2.824 (2)	162.4 (19)
O2—H2A⋯N1	0.88 (2)	1.95 (2)	2.7563 (18)	152.1 (18)
C3—H3A⋯O2	0.96	2.64	3.411 (3)	137
C9—H9A⋯Cgⁱ	0.93	2.77	3.593 (2)	148
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1001222

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814010241/bt6979sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814010241/bt6979Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814010241/bt6979Isup3.cml

checkCIF report

Comment top

Diamine bis(phenolate) compounds and its derivatives represent the dominant class of compounds that are used as tripodal tetradentate ligands with an N₂O₂ donor set (Hirotsu et al., 1997, 1998). The steric factors of substituents in the tetradentate ligands are especially important in complexation of agents for polymerization reactions.

The molecular structure of the title compound and the atom-numbering scheme are shown in Figure 1. The crystal structure shows trigonal pyramidal geometries around N1 [sum of C—N—C angles = 332.05 (18)° and N2 [sum of C—N—C angles = 330.37 (13)°], and is comparable with related structures (Abrahams et al., 2009; Maity et al., 2006; Janas et al., 2012). The aromatic ring which is substituted with tert-butyl groups is slightly more distorted in comparison to unsubstituted one due to the steric hindrance. The molecular structure is stabilized by three hydrogen bonds between hydroxyl groups and amine nitrogen atoms (Figure 1) and one of a C—H···O type. This pattern of interactions influences the dihedral angle between aromatic moieties which amounts 73.88 (57)°. Such stabilization is also observed for structures when both aromatic rings are substituted (Maity et al., 2006; Janas et al., 2012), in contrast to the unsubstituted molecule (Abrahams et al., 2009). All remaining bond distances and angles are normal and in good agreement with the geometries of other diamine bis(phenolates) (Abrahams et al., 2009; Maity et al., 2006; Janas et al., 2012). Strong intermolecular interactions were not found in the crystal. The structure is stabilized by weak C—H···π interactions.

Related literature top

For general background to the use of diaminebis(aryloxido) compounds as tetradentate ligands, see: Hirotsu et al. (1998, 1997); Dutta et al. (2011). For related structures, see: Abrahams et al. (2009); Maity et al. (2006); Janas et al. (2012).

Experimental top

The compound was prepared according to literature procedure (Dutta et al., 2011). Crystals suitable for X-ray crystal structure analysis were grown from methanol.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% displacement ellipsoids (arbitrary spheres for the H atoms).
	Fig. 2. A packing diagram of the title compound.

2,4-Di-tert-butyl-6-({[2-(dimethylamino)ethyl](2-hydroxybenzyl)amino}methyl)phenol top

Crystal data top

C₂₆H₄₀N₂O₂	F(000) = 904
M_r = 412.60	D_x = 1.077 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.3002 (7) Å	Cell parameters from 17015 reflections
b = 13.3758 (7) Å	θ = 3.0–26.0°
c = 15.5662 (9) Å	µ = 0.07 mm⁻¹
β = 96.377 (5)°	T = 150 K
V = 2545.2 (2) Å³	Cubic, colourless
Z = 4	0.4 × 0.37 × 0.35 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	2292 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	R_int = 0.047
Graphite monochromator	θ_max = 26.0°, θ_min = 3.0°
Detector resolution: 10.4508 pixels mm^-1	h = −15→15
ω–scan	k = −16→9
17015 measured reflections	l = −19→19
4964 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0474P)²] where P = (F_o² + 2F_c²)/3
S = 0.78	(Δ/σ)_max < 0.001
4964 reflections	Δρ_max = 0.22 e Å⁻³
277 parameters	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₆H₄₀N₂O₂	V = 2545.2 (2) Å³
M_r = 412.60	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3002 (7) Å	µ = 0.07 mm⁻¹
b = 13.3758 (7) Å	T = 150 K
c = 15.5662 (9) Å	0.4 × 0.37 × 0.35 mm
β = 96.377 (5)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	2292 reflections with I > 2σ(I)
17015 measured reflections	R_int = 0.047
4964 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 0.78	Δρ_max = 0.22 e Å⁻³
4964 reflections	Δρ_min = −0.18 e Å⁻³
277 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.

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

	x	y	z	U_iso*/U_eq
N1	0.47272 (11)	0.82096 (10)	0.29297 (9)	0.0297 (4)
N2	0.35360 (14)	0.71832 (12)	0.15196 (11)	0.0516 (5)
O1	0.27532 (12)	0.91451 (11)	0.17200 (8)	0.0573 (4)
H1A	0.3077 (17)	0.8489 (17)	0.1774 (13)	0.086*
O2	0.56148 (11)	0.93511 (9)	0.17087 (8)	0.0449 (4)
H2A	0.5129 (16)	0.9043 (14)	0.1990 (13)	0.067*
C1	0.49556 (15)	0.71454 (12)	0.27880 (12)	0.0409 (5)
H1B	0.5097	0.6816	0.3344	0.049*
H1C	0.5613	0.7092	0.2500	0.049*
C2	0.40348 (16)	0.66064 (14)	0.22545 (13)	0.0501 (6)
H2B	0.4314	0.5985	0.2044	0.060*
H2C	0.3475	0.6439	0.2623	0.060*
C3	0.4308 (2)	0.72638 (16)	0.08655 (14)	0.0735 (7)
H3A	0.4974	0.7570	0.1119	0.110*
H3B	0.3990	0.7666	0.0392	0.110*
H3C	0.4464	0.6609	0.0659	0.110*
C4	0.2528 (2)	0.67198 (19)	0.11449 (18)	0.0988 (9)
H4A	0.2046	0.7223	0.0880	0.148*
H4B	0.2183	0.6388	0.1590	0.148*
H4C	0.2687	0.6241	0.0717	0.148*
C5	0.37250 (14)	0.83566 (13)	0.33576 (11)	0.0344 (5)
H5A	0.3883	0.8212	0.3969	0.041*
H5B	0.3167	0.7892	0.3117	0.041*
C6	0.32984 (14)	0.94016 (13)	0.32456 (12)	0.0331 (4)
C7	0.28295 (15)	0.97286 (14)	0.24381 (13)	0.0405 (5)
C8	0.23990 (16)	1.06898 (15)	0.23475 (14)	0.0508 (5)
H8A	0.2085	1.0906	0.1808	0.061*
C9	0.24319 (17)	1.13236 (15)	0.30464 (16)	0.0551 (6)
H9A	0.2142	1.1964	0.2977	0.066*
C10	0.28917 (17)	1.10118 (16)	0.38444 (15)	0.0547 (6)
H10A	0.2914	1.1437	0.4319	0.066*
C11	0.33222 (15)	1.00577 (14)	0.39350 (12)	0.0443 (5)
H11A	0.3638	0.9850	0.4476	0.053*
C12	0.56595 (14)	0.86832 (13)	0.34509 (11)	0.0351 (5)
H12A	0.5835	0.8298	0.3976	0.042*
H12B	0.5444	0.9347	0.3617	0.042*
C13	0.66716 (14)	0.87681 (12)	0.29899 (11)	0.0320 (4)
C14	0.66188 (15)	0.91250 (12)	0.21458 (11)	0.0336 (4)
C15	0.75646 (16)	0.92661 (12)	0.17339 (12)	0.0377 (5)
C16	0.85514 (16)	0.90452 (13)	0.22224 (13)	0.0457 (5)
H16A	0.9192	0.9150	0.1969	0.055*
C17	0.86462 (15)	0.86777 (14)	0.30655 (14)	0.0453 (5)
C18	0.76839 (15)	0.85408 (13)	0.34324 (12)	0.0398 (5)
H18A	0.7716	0.8289	0.3992	0.048*
C19	0.75220 (17)	0.96199 (14)	0.07887 (12)	0.0477 (5)
C20	0.6966 (2)	1.06485 (15)	0.06686 (14)	0.0759 (7)
H20A	0.6236	1.0608	0.0830	0.114*
H20B	0.6937	1.0848	0.0074	0.114*
H20C	0.7376	1.1132	0.1027	0.114*
C21	0.69022 (19)	0.88603 (16)	0.01895 (13)	0.0700 (7)
H21A	0.6177	0.8777	0.0351	0.105*
H21B	0.7279	0.8231	0.0237	0.105*
H21C	0.6861	0.9095	−0.0396	0.105*
C22	0.86723 (18)	0.97404 (17)	0.04988 (15)	0.0780 (8)
H22A	0.8609	0.9961	−0.0091	0.117*
H22B	0.9047	0.9110	0.0548	0.117*
H22C	0.9077	1.0225	0.0860	0.117*
C23	0.97742 (17)	0.84687 (19)	0.35613 (16)	0.0669 (7)
C24	0.9681 (2)	0.7884 (2)	0.43981 (19)	0.1249 (13)
H24A	0.9248	0.8258	0.4762	0.187*
H24B	1.0398	0.7778	0.4695	0.187*
H24C	0.9339	0.7250	0.4261	0.187*
C25	1.0477 (2)	0.7853 (2)	0.3005 (2)	0.1166 (11)
H25A	1.0562	0.8211	0.2482	0.175*
H25B	1.0128	0.7223	0.2865	0.175*
H25C	1.1183	0.7739	0.3319	0.175*
C26	1.0338 (2)	0.9463 (2)	0.37872 (19)	0.1113 (10)
H26A	1.0413	0.9828	0.3266	0.167*
H26B	1.1048	0.9343	0.4091	0.167*
H26C	0.9907	0.9845	0.4147	0.167*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0285 (9)	0.0291 (8)	0.0319 (9)	−0.0003 (7)	0.0056 (7)	0.0007 (7)
N2	0.0611 (12)	0.0471 (10)	0.0436 (11)	0.0080 (10)	−0.0073 (9)	−0.0106 (9)
O1	0.0767 (11)	0.0558 (9)	0.0378 (8)	0.0229 (8)	−0.0003 (7)	−0.0001 (8)
O2	0.0436 (9)	0.0540 (9)	0.0377 (8)	0.0040 (7)	0.0079 (6)	0.0137 (7)
C1	0.0445 (12)	0.0346 (11)	0.0439 (12)	0.0056 (10)	0.0068 (10)	0.0058 (9)
C2	0.0594 (15)	0.0370 (12)	0.0540 (14)	−0.0013 (11)	0.0073 (11)	−0.0051 (11)
C3	0.112 (2)	0.0638 (15)	0.0458 (14)	0.0141 (15)	0.0120 (14)	−0.0037 (12)
C4	0.0679 (19)	0.097 (2)	0.122 (2)	0.0002 (16)	−0.0302 (17)	−0.0425 (18)
C5	0.0319 (11)	0.0385 (11)	0.0336 (11)	−0.0021 (9)	0.0074 (9)	0.0053 (9)
C6	0.0273 (10)	0.0359 (11)	0.0378 (11)	−0.0006 (9)	0.0109 (8)	0.0010 (10)
C7	0.0424 (13)	0.0417 (12)	0.0394 (12)	0.0049 (10)	0.0133 (10)	0.0010 (10)
C8	0.0541 (14)	0.0483 (13)	0.0519 (14)	0.0123 (11)	0.0143 (11)	0.0161 (12)
C9	0.0554 (15)	0.0361 (12)	0.0785 (18)	0.0055 (11)	0.0285 (13)	0.0044 (13)
C10	0.0543 (15)	0.0457 (14)	0.0667 (17)	−0.0022 (11)	0.0182 (12)	−0.0141 (12)
C11	0.0410 (13)	0.0488 (13)	0.0442 (13)	−0.0008 (10)	0.0091 (10)	−0.0020 (11)
C12	0.0358 (12)	0.0401 (11)	0.0297 (11)	0.0012 (9)	0.0061 (9)	0.0030 (9)
C13	0.0319 (12)	0.0312 (10)	0.0334 (11)	−0.0018 (9)	0.0064 (9)	0.0001 (9)
C14	0.0366 (12)	0.0285 (10)	0.0362 (11)	0.0013 (9)	0.0062 (9)	0.0012 (9)
C15	0.0451 (13)	0.0280 (10)	0.0428 (12)	−0.0041 (9)	0.0169 (10)	0.0001 (9)
C16	0.0397 (13)	0.0431 (12)	0.0580 (14)	−0.0096 (10)	0.0220 (11)	0.0009 (11)
C17	0.0313 (13)	0.0474 (12)	0.0576 (14)	−0.0058 (10)	0.0066 (11)	0.0001 (11)
C18	0.0379 (13)	0.0438 (12)	0.0376 (12)	−0.0071 (10)	0.0038 (10)	0.0032 (9)
C19	0.0650 (15)	0.0387 (12)	0.0440 (12)	−0.0021 (11)	0.0267 (11)	0.0042 (10)
C20	0.121 (2)	0.0540 (14)	0.0595 (15)	0.0186 (14)	0.0394 (14)	0.0210 (12)
C21	0.098 (2)	0.0701 (16)	0.0453 (14)	−0.0130 (14)	0.0229 (13)	−0.0015 (12)
C22	0.0887 (19)	0.0829 (17)	0.0714 (16)	−0.0115 (15)	0.0486 (14)	0.0091 (14)
C23	0.0317 (14)	0.0890 (19)	0.0786 (18)	−0.0103 (13)	−0.0003 (12)	0.0107 (15)
C24	0.0437 (16)	0.203 (4)	0.121 (2)	−0.0086 (19)	−0.0222 (16)	0.078 (2)
C25	0.0521 (17)	0.152 (3)	0.144 (3)	0.0380 (18)	0.0031 (18)	−0.006 (2)
C26	0.0636 (19)	0.146 (3)	0.121 (2)	−0.0468 (18)	−0.0043 (17)	−0.016 (2)

Geometric parameters (Å, º) top

N1—C12	1.472 (2)	C12—H12B	0.9700
N1—C1	1.472 (2)	C13—C18	1.388 (2)
N1—C5	1.478 (2)	C13—C14	1.393 (2)
N2—C4	1.450 (2)	C14—C15	1.402 (2)
N2—C2	1.457 (2)	C15—C16	1.391 (2)
N2—C3	1.471 (2)	C15—C19	1.541 (2)
O1—C7	1.358 (2)	C16—C17	1.394 (2)
O1—H1A	0.96 (2)	C16—H16A	0.9300
O2—C14	1.376 (2)	C17—C18	1.382 (2)
O2—H2A	0.88 (2)	C17—C23	1.537 (3)
C1—C2	1.511 (2)	C18—H18A	0.9300
C1—H1B	0.9700	C19—C21	1.525 (3)
C1—H1C	0.9700	C19—C20	1.539 (3)
C2—H2B	0.9700	C19—C22	1.541 (3)
C2—H2C	0.9700	C20—H20A	0.9600
C3—H3A	0.9600	C20—H20B	0.9600
C3—H3B	0.9600	C20—H20C	0.9600
C3—H3C	0.9600	C21—H21A	0.9600
C4—H4A	0.9600	C21—H21B	0.9600
C4—H4B	0.9600	C21—H21C	0.9600
C4—H4C	0.9600	C22—H22A	0.9600
C5—C6	1.496 (2)	C22—H22B	0.9600
C5—H5A	0.9700	C22—H22C	0.9600
C5—H5B	0.9700	C23—C26	1.523 (3)
C6—C11	1.384 (2)	C23—C25	1.530 (3)
C6—C7	1.394 (2)	C23—C24	1.535 (3)
C7—C8	1.392 (2)	C24—H24A	0.9600
C8—C9	1.376 (3)	C24—H24B	0.9600
C8—H8A	0.9300	C24—H24C	0.9600
C9—C10	1.371 (3)	C25—H25A	0.9600
C9—H9A	0.9300	C25—H25B	0.9600
C10—C11	1.383 (3)	C25—H25C	0.9600
C10—H10A	0.9300	C26—H26A	0.9600
C11—H11A	0.9300	C26—H26B	0.9600
C12—C13	1.509 (2)	C26—H26C	0.9600
C12—H12A	0.9700

C12—N1—C1	110.41 (13)	C14—C13—C12	121.34 (16)
C12—N1—C5	109.39 (13)	O2—C14—C13	119.15 (16)
C1—N1—C5	112.25 (13)	O2—C14—C15	119.28 (16)
C4—N2—C2	110.86 (18)	C13—C14—C15	121.57 (17)
C4—N2—C3	109.99 (18)	C16—C15—C14	116.07 (17)
C2—N2—C3	109.52 (17)	C16—C15—C19	121.50 (17)
C7—O1—H1A	117.5 (13)	C14—C15—C19	122.41 (18)
C14—O2—H2A	105.8 (13)	C15—C16—C17	124.50 (17)
N1—C1—C2	113.57 (14)	C15—C16—H16A	117.8
N1—C1—H1B	108.9	C17—C16—H16A	117.8
C2—C1—H1B	108.9	C18—C17—C16	116.72 (18)
N1—C1—H1C	108.9	C18—C17—C23	122.4 (2)
C2—C1—H1C	108.9	C16—C17—C23	120.89 (18)
H1B—C1—H1C	107.7	C17—C18—C13	121.88 (18)
N2—C2—C1	113.78 (15)	C17—C18—H18A	119.1
N2—C2—H2B	108.8	C13—C18—H18A	119.1
C1—C2—H2B	108.8	C21—C19—C20	109.63 (19)
N2—C2—H2C	108.8	C21—C19—C22	107.67 (17)
C1—C2—H2C	108.8	C20—C19—C22	106.35 (16)
H2B—C2—H2C	107.7	C21—C19—C15	109.94 (15)
N2—C3—H3A	109.5	C20—C19—C15	110.98 (15)
N2—C3—H3B	109.5	C22—C19—C15	112.14 (18)
H3A—C3—H3B	109.5	C19—C20—H20A	109.5
N2—C3—H3C	109.5	C19—C20—H20B	109.5
H3A—C3—H3C	109.5	H20A—C20—H20B	109.5
H3B—C3—H3C	109.5	C19—C20—H20C	109.5
N2—C4—H4A	109.5	H20A—C20—H20C	109.5
N2—C4—H4B	109.5	H20B—C20—H20C	109.5
H4A—C4—H4B	109.5	C19—C21—H21A	109.5
N2—C4—H4C	109.5	C19—C21—H21B	109.5
H4A—C4—H4C	109.5	H21A—C21—H21B	109.5
H4B—C4—H4C	109.5	C19—C21—H21C	109.5
N1—C5—C6	111.78 (13)	H21A—C21—H21C	109.5
N1—C5—H5A	109.3	H21B—C21—H21C	109.5
C6—C5—H5A	109.3	C19—C22—H22A	109.5
N1—C5—H5B	109.3	C19—C22—H22B	109.5
C6—C5—H5B	109.3	H22A—C22—H22B	109.5
H5A—C5—H5B	107.9	C19—C22—H22C	109.5
C11—C6—C7	118.12 (17)	H22A—C22—H22C	109.5
C11—C6—C5	121.66 (17)	H22B—C22—H22C	109.5
C7—C6—C5	120.18 (16)	C26—C23—C25	109.2 (2)
O1—C7—C8	117.18 (18)	C26—C23—C24	108.9 (2)
O1—C7—C6	123.08 (16)	C25—C23—C24	107.8 (2)
C8—C7—C6	119.73 (18)	C26—C23—C17	108.6 (2)
C9—C8—C7	120.8 (2)	C25—C23—C17	110.4 (2)
C9—C8—H8A	119.6	C24—C23—C17	111.77 (18)
C7—C8—H8A	119.6	C23—C24—H24A	109.5
C10—C9—C8	120.11 (19)	C23—C24—H24B	109.5
C10—C9—H9A	119.9	H24A—C24—H24B	109.5
C8—C9—H9A	119.9	C23—C24—H24C	109.5
C9—C10—C11	119.2 (2)	H24A—C24—H24C	109.5
C9—C10—H10A	120.4	H24B—C24—H24C	109.5
C11—C10—H10A	120.4	C23—C25—H25A	109.5
C10—C11—C6	122.08 (19)	C23—C25—H25B	109.5
C10—C11—H11A	119.0	H25A—C25—H25B	109.5
C6—C11—H11A	119.0	C23—C25—H25C	109.5
N1—C12—C13	113.81 (14)	H25A—C25—H25C	109.5
N1—C12—H12A	108.8	H25B—C25—H25C	109.5
C13—C12—H12A	108.8	C23—C26—H26A	109.5
N1—C12—H12B	108.8	C23—C26—H26B	109.5
C13—C12—H12B	108.8	H26A—C26—H26B	109.5
H12A—C12—H12B	107.7	C23—C26—H26C	109.5
C18—C13—C14	119.23 (16)	H26A—C26—H26C	109.5
C18—C13—C12	119.32 (16)	H26B—C26—H26C	109.5

C12—N1—C1—C2	−179.85 (14)	C18—C13—C14—C15	−0.4 (2)
C5—N1—C1—C2	57.8 (2)	C12—C13—C14—C15	175.84 (16)
C4—N2—C2—C1	−168.19 (17)	O2—C14—C15—C16	178.47 (15)
C3—N2—C2—C1	70.3 (2)	C13—C14—C15—C16	−1.1 (2)
N1—C1—C2—N2	41.7 (2)	O2—C14—C15—C19	−3.0 (2)
C12—N1—C5—C6	75.50 (18)	C13—C14—C15—C19	177.50 (16)
C1—N1—C5—C6	−161.58 (14)	C14—C15—C16—C17	1.7 (3)
N1—C5—C6—C11	−111.69 (18)	C19—C15—C16—C17	−176.85 (17)
N1—C5—C6—C7	70.4 (2)	C15—C16—C17—C18	−0.8 (3)
C11—C6—C7—O1	−179.36 (16)	C15—C16—C17—C23	−179.12 (18)
C5—C6—C7—O1	−1.4 (3)	C16—C17—C18—C13	−0.7 (3)
C11—C6—C7—C8	−0.3 (3)	C23—C17—C18—C13	177.50 (18)
C5—C6—C7—C8	177.65 (16)	C14—C13—C18—C17	1.3 (3)
O1—C7—C8—C9	179.21 (17)	C12—C13—C18—C17	−174.96 (16)
C6—C7—C8—C9	0.1 (3)	C16—C15—C19—C21	116.8 (2)
C7—C8—C9—C10	0.0 (3)	C14—C15—C19—C21	−61.7 (2)
C8—C9—C10—C11	0.2 (3)	C16—C15—C19—C20	−121.7 (2)
C9—C10—C11—C6	−0.4 (3)	C14—C15—C19—C20	59.8 (2)
C7—C6—C11—C10	0.5 (3)	C16—C15—C19—C22	−2.9 (2)
C5—C6—C11—C10	−177.45 (16)	C14—C15—C19—C22	178.58 (17)
C1—N1—C12—C13	68.05 (18)	C18—C17—C23—C26	−107.3 (2)
C5—N1—C12—C13	−167.94 (13)	C16—C17—C23—C26	70.9 (3)
N1—C12—C13—C18	−136.89 (16)	C18—C17—C23—C25	132.9 (2)
N1—C12—C13—C14	46.9 (2)	C16—C17—C23—C25	−48.9 (3)
C18—C13—C14—O2	−179.92 (15)	C18—C17—C23—C24	12.9 (3)
C12—C13—C14—O2	−3.7 (2)	C16—C17—C23—C24	−168.9 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.96 (2)	2.59 (2)	3.1610 (19)	118.5 (16)
O1—H1A···N2	0.96 (2)	1.89 (2)	2.824 (2)	162.4 (19)
O2—H2A···N1	0.88 (2)	1.95 (2)	2.7563 (18)	152.1 (18)
C3—H3A···O2	0.96	2.64	3.411 (3)	137
C9—H9A···Cgⁱ	0.93	2.77	3.593 (2)	148

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.96 (2)	2.59 (2)	3.1610 (19)	118.5 (16)
O1—H1A···N2	0.96 (2)	1.89 (2)	2.824 (2)	162.4 (19)
O2—H2A···N1	0.88 (2)	1.95 (2)	2.7563 (18)	152.1 (18)
C3—H3A···O2	0.96	2.64	3.411 (3)	137.3
C9—H9A···Cgⁱ	0.93	2.77	3.593 (2)	148

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Acknowledgements

This work was supported by a research grant (grant No. N N209 140840 within 2011–2014) from the Polish National Science Centre. EB is a recipient of a PhD fellowship from a project funded by the European Social Fund.

References

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2,4-Di-tert-butyl-6-({[2-(di­methyl­amino)­eth­yl](2-hy­dr­oxy­benz­yl)amino}­meth­yl)phenol

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2,4-Di-tert-butyl-6-({[2-(dimethylamino)ethyl](2-hydroxybenzyl)amino}methyl)phenol