4,6-Di-tert-butyl-2-({[4-(di­ethyl­amino)­phen­yl]imino}­meth­yl)phenol

Rani, C.V.; Mitu, L.; Chakkaravarthi, G.; Rajagopal, G.

doi:10.1107/S2414314617005727

organic compounds

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ISSN: 2414-3146

Volume 2| Part 4| April 2017| x170572

https://doi.org/10.1107/S2414314617005727

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4,6-Di-tert-butyl-2-({[4-(diethylamino)phenyl]imino}methyl)phenol

C. Vidya Rani,^a L. Mitu,^b G. Chakkaravarthi ^c ^* and G. Rajagopal ^d ^*

^aDepartment of Chemistry, Vaigai College of Engineering, Madurai 625 122, Tamil Nadu, India, ^bDepartment of Chemistry, University of Pitesti, Pitesti 11040, Romania, ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^dPG & Research Department of Chemistry, Chikkanna Government Arts College, Tiruppur 641 602, Tamil Nadu, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, rajagopal18@yahoo.com

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 10 April 2017; accepted 15 April 2017; online 21 April 2017)

The title compound, C₂₅H₃₆N₂O, adopts an E conformation about the C=N bond. The dihedral angle between the aromatic rings is 35.6 (6)°. The molecular structure is stabilized by an O—H⋯N hydrogen bond, which forms an S(6) loop, and weak C—H⋯O contacts. Weak intermolecular C—H⋯π interactions are observed in the crystal packing. The diethylamino group has rotational disorder with site occupancies of 0.85 (2) and 0.15 (2) for the major and minor components, respectively. The structure was refined as a three-component twin.

Keywords: crystal structure; disordered diethylamine moiety; hydrogen bonding.

CCDC reference: 982393

Structure description

Schiff base derivatives are a biologically versatile class of compounds possessing diverse activities, such as anti-inflammatory (Alam et al., 2012 ), anti-bacterial (Sondhi et al., 2006 ), anti-fungal (Jarrahpour et al., 2007 ). We herein, report the synthesis and crystal structure of the title compound (Fig. 1). The bond distances are comparable with similar structures (Rani et al., 2015 , 2017 ).

Figure 1
The molecular structure of the title compound, with atom labelling and 30% probability displacement ellipsoids. The O—H⋯N hydrogen bond is shown as a dashed line.

The dihedral angle between the best planes through the aromatic rings (C5–C10 and C12–C17) is 35.6 (6)°. The C11=N2 bond adopts the E conformation, which allows formation of an intramolecular O1—H1⋯N2 hydrogen bond, resulting in an S(6) ring-motif (Fig. 1 and Table 1). The molecular structure is stabilized by an O—H⋯N hydrogen bond and weak C—H⋯O contacts (Table 1). Weak intermolecular C—H⋯π interactions are also observed in the crystal packing (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.83 (7)	1.82 (11)	2.591 (12)	155 (14)
C23—H23A⋯O1	0.96	2.27	2.947 (17)	127
C24—H24A⋯O1	0.96	2.46	3.071 (16)	121
C2—H2B⋯Cg2ⁱ	0.97	2.87	3.810 (19)	166
C2′—H2′1⋯Cg2ⁱ	0.97	2.60	3.39 (11)	139
Symmetry code: (i) x-1, y, z-1.

Synthesis and crystallization

An ethanolic solution of N¹,N¹-diethylbenzene-1,4-diamine (5 mmol) was magnetically stirred in a round-bottom flask followed by dropwise addition of 3,5-di-tert-butyl-2-hydroxybenzaldehyde (5 mmol) containing 2–3 drops of glacial acetic acid. The reaction mixture was then refluxed for 3 h and upon cooling to room temperature, a yellow precipitate was separated out from the mixture. The precipitate was washed with ethanol and dried in vacuo over anhydrous CaCl₂. Single crystals suitable for X–ray diffraction were obtained by slow evaporation of a solution of the title compound in DMF at room temperature.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The diethylamine group has rotational disorder with occupancies of 0.85 (2) for the major component (atoms C1–C4) and 0.15 (2) for the minor component (atoms C1′–C4′). The command DFIX was used to restrain the N—C and C—C bond lengths involving these atoms to 1.43 (1) and 1.55 (1) Å, respectively. The same anisotropic displacement parameters were used for the disordered equivalent C atoms (C1 & C1′, C2 & C2′, C3 & C3′ and C4 & C4′) using the EADP command. Rigid bond restraints were used for N1—C2′, N1—C4′, N1—C2, N1—C4, N2—C8, C3′-C4′, C5—C6, C3—C4, C6—C7, C18—C21, C15—C16, and C1—C2 bonds, using the DELU command. The structure was refined as a three-component twin. In the absence of significant anomalous scattering effects, the absolute structure parameter is meaningless. Reflections (20 $[\overline{5}]$ ), (10 $[\overline{5}]$ ) and ( $[\overline{1}]$ 05) were omitted in the final cycles of refinement.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₅H₃₆N₂O
M_r	380.56
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	295
a, b, c (Å)	8.9303 (15), 15.572 (3), 9.4824 (16)
β (°)	117.320 (8)
V (Å³)	1171.6 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.28 × 0.24

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.921, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	8432, 8432, 6509
R_int	0.000
θ_max (°)	22.9
(sin θ/λ)_max (Å⁻¹)	0.547

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.189, 1.05
No. of reflections	8432
No. of parameters	277
No. of restraints	26
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.22
Computer programs: APEX2 and SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008 ), SHELXL2016 (Sheldrick, 2015 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 982393

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314617005727/vm4022sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617005727/vm4022Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617005727/vm4022Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015) and PLATON (Spek, 2009).

4,6-Di-tert-butyl-2-({[4-(diethylamino)phenyl]imino}methyl)phenol top

Crystal data top

C₂₅H₃₆N₂O	F(000) = 416
M_r = 380.56	D_x = 1.079 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 8.9303 (15) Å	Cell parameters from 3084 reflections
b = 15.572 (3) Å	θ = 2.4–20.5°
c = 9.4824 (16) Å	µ = 0.07 mm⁻¹
β = 117.320 (8)°	T = 295 K
V = 1171.6 (3) Å³	Block, yellow
Z = 2	0.30 × 0.28 × 0.24 mm

Data collection top

Bruker APEXII CCD diffractometer	8432 independent reflections
Radiation source: fine-focus sealed tube	6509 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
ω and φ scan	θ_max = 22.9°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
T_min = 0.921, T_max = 0.984	k = −17→17
8432 measured reflections	l = −10→10

Refinement top

Refinement on F²	26 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.189	w = 1/[σ²(F_o²) + (0.0973P)² + 0.2985P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
8432 reflections	Δρ_max = 0.20 e Å⁻³
277 parameters	Δρ_min = −0.22 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 3-component twin. The H atom for the hydroxy group was located in a difference-Fourier map and refined with a distance restraint of 0.82 (1) Å, with U_iso(H) = 1.5U_eq(O). All other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C) for aromatic CH, C—H = 0.97 Å and U_iso(H) = 1.2U_eq(C) for CH₂ and C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C) for CH₃.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	−0.077 (3)	0.5191 (13)	−0.506 (3)	0.150 (9)	0.85 (2)
H1A	−0.177280	0.485250	−0.557143	0.225*	0.85 (2)
H1B	−0.010074	0.512597	−0.560645	0.225*	0.85 (2)
H1C	−0.012806	0.500182	−0.397779	0.225*	0.85 (2)
C2	−0.1242 (18)	0.6139 (12)	−0.507 (2)	0.094 (5)	0.85 (2)
H2A	−0.190115	0.632881	−0.616152	0.113*	0.85 (2)
H2B	−0.192852	0.620445	−0.453017	0.113*	0.85 (2)
C3	−0.016 (4)	0.7921 (17)	−0.593 (3)	0.186 (12)	0.85 (2)
H3A	0.015996	0.820295	−0.665562	0.278*	0.85 (2)
H3B	−0.134618	0.780981	−0.645328	0.278*	0.85 (2)
H3C	0.011559	0.828409	−0.502735	0.278*	0.85 (2)
C4	0.081 (2)	0.7066 (14)	−0.5381 (18)	0.107 (6)	0.85 (2)
H4A	0.054761	0.669186	−0.628333	0.128*	0.85 (2)
H4B	0.201674	0.716854	−0.485022	0.128*	0.85 (2)
C1'	−0.175 (19)	0.563 (10)	−0.587 (14)	0.150 (9)	0.15 (2)
H1'1	−0.271543	0.530082	−0.598955	0.225*	0.15 (2)
H1'2	−0.205138	0.598040	−0.678834	0.225*	0.15 (2)
H1'3	−0.085701	0.524662	−0.574063	0.225*	0.15 (2)
C2'	−0.116 (11)	0.621 (8)	−0.438 (12)	0.094 (5)	0.15 (2)
H2'1	−0.205060	0.660315	−0.448596	0.113*	0.15 (2)
H2'2	−0.084905	0.586495	−0.343194	0.113*	0.15 (2)
C3'	0.08 (3)	0.818 (8)	−0.517 (19)	0.186 (12)	0.15 (2)
H3'1	0.043755	0.849312	−0.613457	0.278*	0.15 (2)
H3'2	0.035306	0.847736	−0.451956	0.278*	0.15 (2)
H3'3	0.196242	0.813633	−0.460255	0.278*	0.15 (2)
C4'	−0.002 (14)	0.727 (6)	−0.556 (9)	0.107 (6)	0.15 (2)
H4'1	−0.123560	0.733489	−0.616586	0.128*	0.15 (2)
H4'2	0.036441	0.699583	−0.624836	0.128*	0.15 (2)
C5	0.1139 (15)	0.6770 (9)	−0.2706 (11)	0.057 (3)
C6	0.2514 (14)	0.7334 (8)	−0.2004 (12)	0.067 (3)
H6	0.286148	0.764161	−0.264162	0.080*
C7	0.3341 (14)	0.7435 (8)	−0.0403 (12)	0.063 (3)
H7	0.425305	0.780968	0.001366	0.075*
C8	0.2911 (14)	0.7014 (7)	0.0652 (11)	0.052 (3)
C9	0.1524 (15)	0.6488 (9)	−0.0054 (13)	0.070 (3)
H9	0.115149	0.620270	0.058848	0.084*
C10	0.0672 (13)	0.6366 (8)	−0.1654 (14)	0.066 (3)
H10	−0.025512	0.600110	−0.206012	0.079*
C11	0.4023 (13)	0.6582 (7)	0.3275 (12)	0.057 (3)
H11	0.354071	0.604812	0.289394	0.069*
C12	0.4924 (14)	0.6693 (7)	0.4952 (12)	0.051 (3)
C13	0.5096 (14)	0.6016 (7)	0.5958 (13)	0.060 (3)
H13	0.460269	0.549358	0.550738	0.072*
C14	0.5948 (13)	0.6069 (7)	0.7577 (13)	0.051 (3)
C15	0.6630 (15)	0.6864 (7)	0.8231 (11)	0.052 (2)
H15	0.721045	0.691959	0.932885	0.063*
C16	0.6464 (12)	0.7588 (6)	0.7274 (11)	0.050 (3)
C17	0.5607 (12)	0.7496 (7)	0.5649 (11)	0.049 (3)
C18	0.6143 (16)	0.5287 (8)	0.8651 (13)	0.065 (3)
C19	0.4436 (17)	0.4872 (10)	0.8153 (16)	0.094 (4)
H19A	0.395662	0.470994	0.705493	0.141*
H19B	0.370156	0.527204	0.829953	0.141*
H19C	0.456973	0.437040	0.878934	0.141*
C20	0.7227 (17)	0.4621 (10)	0.8346 (17)	0.093 (4)
H20A	0.675752	0.451327	0.722708	0.140*
H20B	0.724633	0.409644	0.888660	0.140*
H20C	0.835444	0.483593	0.873406	0.140*
C21	0.693 (2)	0.5511 (10)	1.0374 (14)	0.113 (6)
H21A	0.708759	0.499740	1.098732	0.170*
H21B	0.620636	0.589810	1.056491	0.170*
H21C	0.800130	0.578005	1.067742	0.170*
C22	0.7209 (14)	0.8462 (7)	0.8094 (12)	0.055 (3)
C23	0.8412 (17)	0.8824 (9)	0.7467 (17)	0.084 (4)
H23A	0.781027	0.888380	0.633457	0.126*
H23B	0.934110	0.843646	0.773981	0.126*
H23C	0.882885	0.937421	0.794029	0.126*
C24	0.5703 (16)	0.9104 (9)	0.7627 (16)	0.078 (4)
H24A	0.519704	0.921425	0.650623	0.117*
H24B	0.611075	0.963319	0.819554	0.117*
H24C	0.487803	0.885891	0.789197	0.117*
C25	0.8121 (18)	0.8411 (8)	0.9828 (13)	0.079 (4)
H25A	0.863737	0.895478	1.024963	0.119*
H25B	0.897574	0.797584	1.013385	0.119*
H25C	0.734835	0.826746	1.023648	0.119*
N1	0.0275 (13)	0.6674 (8)	−0.4291 (11)	0.088 (3)
N2	0.3832 (11)	0.7164 (6)	0.2262 (10)	0.058 (2)
O1	0.5431 (11)	0.8175 (5)	0.4662 (9)	0.072 (2)
H1	0.488 (16)	0.799 (9)	0.375 (7)	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.14 (2)	0.143 (15)	0.113 (16)	−0.027 (15)	0.016 (16)	−0.044 (15)
C2	0.072 (8)	0.149 (12)	0.057 (10)	−0.021 (7)	0.027 (8)	−0.018 (10)
C3	0.27 (4)	0.139 (16)	0.107 (18)	−0.010 (10)	0.05 (2)	0.043 (13)
C4	0.073 (10)	0.182 (14)	0.064 (8)	−0.016 (9)	0.029 (7)	0.005 (7)
C1'	0.14 (2)	0.143 (15)	0.113 (16)	−0.027 (15)	0.016 (16)	−0.044 (15)
C2'	0.072 (8)	0.149 (12)	0.057 (10)	−0.021 (7)	0.027 (8)	−0.018 (10)
C3'	0.27 (4)	0.139 (16)	0.107 (18)	−0.010 (10)	0.05 (2)	0.043 (13)
C4'	0.073 (10)	0.182 (14)	0.064 (8)	−0.016 (9)	0.029 (7)	0.005 (7)
C5	0.061 (5)	0.070 (8)	0.044 (5)	0.000 (5)	0.026 (4)	−0.004 (5)
C6	0.078 (7)	0.071 (9)	0.060 (4)	−0.011 (5)	0.040 (5)	−0.005 (6)
C7	0.068 (6)	0.058 (8)	0.064 (4)	−0.016 (6)	0.031 (5)	−0.011 (6)
C8	0.066 (6)	0.036 (7)	0.054 (4)	0.004 (6)	0.028 (5)	−0.005 (5)
C9	0.069 (7)	0.079 (10)	0.070 (8)	−0.008 (7)	0.038 (6)	0.009 (7)
C10	0.052 (6)	0.069 (10)	0.069 (8)	−0.019 (6)	0.022 (6)	−0.005 (6)
C11	0.077 (7)	0.032 (7)	0.064 (7)	0.001 (6)	0.033 (6)	0.000 (6)
C12	0.065 (6)	0.036 (7)	0.055 (6)	0.003 (5)	0.029 (5)	0.001 (5)
C13	0.076 (8)	0.035 (7)	0.076 (8)	0.005 (6)	0.041 (6)	0.010 (6)
C14	0.066 (7)	0.038 (7)	0.058 (7)	0.014 (6)	0.036 (6)	0.015 (5)
C15	0.066 (6)	0.037 (6)	0.056 (6)	−0.004 (5)	0.030 (5)	−0.005 (4)
C16	0.057 (6)	0.040 (6)	0.062 (6)	−0.003 (6)	0.036 (5)	−0.001 (4)
C17	0.061 (6)	0.044 (7)	0.048 (6)	0.002 (6)	0.028 (5)	0.003 (5)
C18	0.079 (8)	0.043 (7)	0.074 (5)	0.002 (7)	0.037 (6)	0.015 (6)
C19	0.100 (9)	0.080 (12)	0.117 (10)	−0.010 (8)	0.062 (8)	0.029 (8)
C20	0.092 (10)	0.062 (10)	0.127 (11)	0.020 (8)	0.053 (9)	0.033 (8)
C21	0.160 (15)	0.089 (12)	0.069 (5)	−0.024 (11)	0.034 (9)	0.022 (7)
C22	0.070 (7)	0.044 (8)	0.056 (7)	−0.011 (6)	0.034 (6)	−0.010 (5)
C23	0.093 (9)	0.067 (10)	0.106 (10)	−0.027 (8)	0.057 (8)	−0.009 (7)
C24	0.099 (10)	0.041 (8)	0.108 (9)	0.000 (7)	0.059 (8)	−0.004 (6)
C25	0.103 (10)	0.061 (9)	0.069 (8)	−0.025 (8)	0.035 (7)	−0.021 (6)
N1	0.081 (5)	0.121 (9)	0.063 (6)	−0.019 (6)	0.035 (5)	−0.017 (5)
N2	0.065 (5)	0.049 (6)	0.056 (4)	−0.001 (5)	0.024 (4)	−0.004 (5)
O1	0.096 (6)	0.046 (5)	0.067 (5)	−0.006 (5)	0.033 (5)	0.008 (4)

Geometric parameters (Å, º) top

C1—C2	1.53 (2)	C11—C12	1.425 (14)
C1—H1A	0.9600	C11—H11	0.9300
C1—H1B	0.9600	C12—C13	1.383 (15)
C1—H1C	0.9600	C12—C17	1.416 (14)
C2—N1	1.468 (15)	C13—C14	1.368 (12)
C2—H2A	0.9700	C13—H13	0.9300
C2—H2B	0.9700	C14—C15	1.393 (15)
C3—C4	1.54 (2)	C14—C18	1.545 (16)
C3—H3A	0.9600	C15—C16	1.411 (15)
C3—H3B	0.9600	C15—H15	0.9300
C3—H3C	0.9600	C16—C17	1.377 (12)
C4—N1	1.458 (16)	C16—C22	1.557 (14)
C4—H4A	0.9700	C17—O1	1.372 (12)
C4—H4B	0.9700	C18—C21	1.493 (17)
C1'—C2'	1.55 (2)	C18—C19	1.518 (17)
C1'—H1'1	0.9600	C18—C20	1.534 (18)
C1'—H1'2	0.9600	C19—H19A	0.9600
C1'—H1'3	0.9600	C19—H19B	0.9600
C2'—N1	1.44 (2)	C19—H19C	0.9600
C2'—H2'1	0.9700	C20—H20A	0.9600
C2'—H2'2	0.9700	C20—H20B	0.9600
C3'—C4'	1.55 (2)	C20—H20C	0.9600
C3'—H3'1	0.9600	C21—H21A	0.9600
C4'—N1	1.44 (2)	C21—H21B	0.9600
C4'—H4'1	0.9700	C21—H21C	0.9600
C4'—H4'2	0.9700	C22—C25	1.464 (14)
C5—N1	1.346 (12)	C22—C23	1.553 (16)
C5—C10	1.394 (16)	C22—C24	1.569 (17)
C5—C6	1.404 (17)	C23—H23A	0.9600
C6—C7	1.359 (14)	C23—H23B	0.9600
C6—H6	0.9300	C23—H23C	0.9600
C7—C8	1.389 (15)	C24—H24A	0.9600
C7—H7	0.9300	C24—H24B	0.9600
C8—C9	1.375 (15)	C24—H24C	0.9600
C8—N2	1.382 (12)	C25—H25A	0.9600
C9—C10	1.363 (15)	C25—H25B	0.9600
C9—H9	0.9300	C25—H25C	0.9600
C10—H10	0.9300	O1—H1	0.83 (2)
C11—N2	1.273 (12)

C2—C1—H1A	109.5	C12—C13—H13	118.1
C2—C1—H1B	109.5	C13—C14—C15	117.2 (9)
H1A—C1—H1B	109.5	C13—C14—C18	121.9 (10)
C2—C1—H1C	109.5	C15—C14—C18	120.9 (9)
H1A—C1—H1C	109.5	C14—C15—C16	121.9 (9)
H1B—C1—H1C	109.5	C14—C15—H15	119.1
N1—C2—C1	110.7 (15)	C16—C15—H15	119.1
N1—C2—H2A	109.5	C17—C16—C15	118.5 (9)
C1—C2—H2A	109.5	C17—C16—C22	122.7 (8)
N1—C2—H2B	109.5	C15—C16—C22	118.8 (8)
C1—C2—H2B	109.5	O1—C17—C16	120.9 (9)
H2A—C2—H2B	108.1	O1—C17—C12	118.2 (8)
C4—C3—H3A	109.5	C16—C17—C12	120.9 (9)
C4—C3—H3B	109.5	C21—C18—C19	109.9 (11)
H3A—C3—H3B	109.5	C21—C18—C20	110.1 (11)
C4—C3—H3C	109.5	C19—C18—C20	106.5 (11)
H3A—C3—H3C	109.5	C21—C18—C14	113.0 (11)
H3B—C3—H3C	109.5	C19—C18—C14	109.7 (9)
N1—C4—C3	106.6 (19)	C20—C18—C14	107.4 (10)
N1—C4—H4A	110.4	C18—C19—H19A	109.5
C3—C4—H4A	110.4	C18—C19—H19B	109.5
N1—C4—H4B	110.4	H19A—C19—H19B	109.5
C3—C4—H4B	110.4	C18—C19—H19C	109.5
H4A—C4—H4B	108.6	H19A—C19—H19C	109.5
C2'—C1'—H1'1	109.5	H19B—C19—H19C	109.5
C2'—C1'—H1'2	109.5	C18—C20—H20A	109.5
H1'1—C1'—H1'2	109.5	C18—C20—H20B	109.5
C2'—C1'—H1'3	109.5	H20A—C20—H20B	109.5
H1'1—C1'—H1'3	109.5	C18—C20—H20C	109.5
H1'2—C1'—H1'3	109.5	H20A—C20—H20C	109.5
N1—C2'—C1'	105 (8)	H20B—C20—H20C	109.5
N1—C2'—H2'1	110.6	C18—C21—H21A	109.5
C1'—C2'—H2'1	110.6	C18—C21—H21B	109.5
N1—C2'—H2'2	110.6	H21A—C21—H21B	109.5
C1'—C2'—H2'2	110.6	C18—C21—H21C	109.5
H2'1—C2'—H2'2	108.8	H21A—C21—H21C	109.5
C4'—C3'—H3'1	109.5	H21B—C21—H21C	109.5
C4'—C3'—H3'3	109.5	C25—C22—C23	108.9 (10)
H3'2—C3'—H3'3	109.5	C25—C22—C16	113.8 (9)
N1—C4'—C3'	120 (9)	C23—C22—C16	109.7 (8)
N1—C4'—H4'1	107.3	C25—C22—C24	108.4 (10)
N1—C4'—H4'2	107.3	C23—C22—C24	108.3 (9)
C3'—C4'—H4'2	107.3	C16—C22—C24	107.6 (9)
H4'1—C4'—H4'2	106.9	C22—C23—H23A	109.5
N1—C5—C10	122.8 (11)	C22—C23—H23B	109.5
N1—C5—C6	121.8 (10)	H23A—C23—H23B	109.5
C10—C5—C6	115.2 (9)	C22—C23—H23C	109.5
C7—C6—C5	120.8 (11)	H23A—C23—H23C	109.5
C7—C6—H6	119.6	H23B—C23—H23C	109.5
C5—C6—H6	119.6	C22—C24—H24A	109.5
C6—C7—C8	124.1 (11)	C22—C24—H24B	109.5
C6—C7—H7	117.9	H24A—C24—H24B	109.5
C8—C7—H7	117.9	C22—C24—H24C	109.5
C9—C8—N2	125.8 (9)	H24A—C24—H24C	109.5
C9—C8—C7	114.6 (9)	H24B—C24—H24C	109.5
N2—C8—C7	119.6 (10)	C22—C25—H25A	109.5
C10—C9—C8	122.8 (10)	C22—C25—H25B	109.5
C10—C9—H9	118.6	H25A—C25—H25B	109.5
C8—C9—H9	118.6	C22—C25—H25C	109.5
C9—C10—C5	122.5 (11)	H25A—C25—H25C	109.5
C9—C10—H10	118.8	H25B—C25—H25C	109.5
C5—C10—H10	118.8	C5—N1—C4'	131 (5)
N2—C11—C12	124.6 (10)	C5—N1—C2'	99 (4)
N2—C11—H11	117.7	C4'—N1—C2'	117 (7)
C12—C11—H11	117.7	C5—N1—C4	122.6 (11)
C13—C12—C17	117.6 (9)	C5—N1—C2	123.4 (11)
C13—C12—C11	120.3 (10)	C4—N1—C2	114.0 (11)
C17—C12—C11	122.0 (9)	C11—N2—C8	121.3 (9)
C14—C13—C12	123.8 (11)	C17—O1—H1	106 (10)
C14—C13—H13	118.1

N1—C5—C6—C7	178.4 (11)	C13—C14—C18—C19	−49.8 (15)
C10—C5—C6—C7	2.6 (18)	C15—C14—C18—C19	129.6 (12)
C5—C6—C7—C8	−0.8 (18)	C13—C14—C18—C20	65.5 (13)
C6—C7—C8—C9	−1.6 (17)	C15—C14—C18—C20	−115.1 (12)
C6—C7—C8—N2	−179.8 (11)	C17—C16—C22—C25	−178.0 (10)
N2—C8—C9—C10	−179.9 (11)	C15—C16—C22—C25	3.9 (15)
C7—C8—C9—C10	2.1 (17)	C17—C16—C22—C23	−55.7 (13)
C8—C9—C10—C5	−0.2 (19)	C15—C16—C22—C23	126.1 (11)
N1—C5—C10—C9	−177.9 (13)	C17—C16—C22—C24	61.9 (12)
C6—C5—C10—C9	−2.2 (18)	C15—C16—C22—C24	−116.2 (10)
N2—C11—C12—C13	−178.5 (11)	C10—C5—N1—C4'	146 (7)
N2—C11—C12—C17	4.3 (17)	C6—C5—N1—C4'	−29 (7)
C17—C12—C13—C14	−3.1 (17)	C10—C5—N1—C2'	8 (6)
C11—C12—C13—C14	179.6 (11)	C6—C5—N1—C2'	−167 (6)
C12—C13—C14—C15	2.1 (16)	C10—C5—N1—C4	−177.2 (16)
C12—C13—C14—C18	−178.4 (11)	C6—C5—N1—C4	7 (2)
C13—C14—C15—C16	−0.4 (17)	C10—C5—N1—C2	0 (2)
C18—C14—C15—C16	−179.8 (10)	C6—C5—N1—C2	−175.3 (15)
C14—C15—C16—C17	−0.2 (16)	C3'—C4'—N1—C5	2 (19)
C14—C15—C16—C22	178.0 (9)	C3'—C4'—N1—C2'	134 (15)
C15—C16—C17—O1	−179.0 (9)	C1'—C2'—N1—C5	−149 (10)
C22—C16—C17—O1	2.9 (14)	C1'—C2'—N1—C4'	65 (13)
C15—C16—C17—C12	−0.8 (14)	C3—C4—N1—C5	−95 (2)
C22—C16—C17—C12	−178.9 (9)	C3—C4—N1—C2	87.3 (19)
C13—C12—C17—O1	−179.4 (10)	C1—C2—N1—C5	−82 (2)
C11—C12—C17—O1	−2.1 (15)	C1—C2—N1—C4	96 (2)
C13—C12—C17—C16	2.3 (15)	C12—C11—N2—C8	−178.7 (10)
C11—C12—C17—C16	179.6 (10)	C9—C8—N2—C11	33.1 (16)
C13—C14—C18—C21	−172.9 (12)	C7—C8—N2—C11	−149.0 (11)
C15—C14—C18—C21	6.5 (16)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.83 (7)	1.82 (11)	2.591 (12)	155 (14)
C23—H23A···O1	0.96	2.27	2.947 (17)	127
C24—H24A···O1	0.96	2.46	3.071 (16)	121
C2—H2B···Cg2ⁱ	0.97	2.87	3.810 (19)	166
C2′—H2′1···Cg2ⁱ	0.97	2.60	3.39 (11)	139

Symmetry code: (i) x−1, y, z−1.

Acknowledgements

The authors acknowledge the SAIF, IIT, Madras, for the data collection.

References

Alam, M. S., Choi, J. & Lee, D. (2012). Bioorg. Med. Chem. 20, 4103–4108. Web of Science CrossRef CAS PubMed Google Scholar
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Jarrahpour, A., Khalili, D., De Clercq, E., Salmi, C. & Brunel, J. M. (2007). Molecules, 12, 1720–1730. Web of Science CrossRef PubMed CAS Google Scholar
Rani, C. V., Chakkaravarthi, G. & Rajagopal, G. (2015). Acta Cryst. E71, o503. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rani, C. V., Mitu, L., Chakkaravarthi, G. & Rajagopal, G. (2017). IUCrData, 2, x170396. Google Scholar
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IUCrDATA

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Volume 2| Part 4| April 2017| x170572

https://doi.org/10.1107/S2414314617005727

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4,6-Di-tert-butyl-2-({[4-(di­ethyl­amino)­phen­yl]imino}­meth­yl)phenol

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

4,6-Di-tert-butyl-2-({[4-(diethylamino)phenyl]imino}methyl)phenol