organic compounds
4,4′-Dimethyl-2,2′-[imidazolidine-1,3-diylbis(methylene)]diphenol
aUniversidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No.45-03, Bogotá, Código Postal 111321, Colombia, and bInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
*Correspondence e-mail: ariverau@unal.edu.co
The imidazolidine ring in the title compound, C19H24N2O2, adopts a twist conformation and its mean plane (r.m.s. deviation = 0.19 Å) makes dihedral angles of 72.38 (9) and 71.64 (9)° with the two pendant aromatic rings. The dihedral angle between the phenyl rings is 55.94 (8)°. The molecular structure shows the presence of two intramolecular O—H⋯N hydrogen bonds between the phenolic hydroxyl groups and N atoms with graph-set motif S(6). In the crystal, C—H⋯O hydrogen bonds lead to the formation of chains along the b-axis direction.
Related literature
For the anti-inflammatory and analgesic properties of imidazolidines, see: Sharma & Khan (2001). For related structures, see: Rivera et al. (2011, 2012). For the preparation of the title compound, see: Rivera et al. (1993). For standard bond lengths, see: Allen et al. (1987). For ring conformations, see Cremer & Pople (1975). For hydrogen-bond graph-set nomenclature, see: Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2010); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: Superflip (Palatinus & Chapuis 2007); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006.
Supporting information
10.1107/S1600536812042808/lr2083sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812042808/lr2083Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812042808/lr2083Isup3.cml
The position of hydrogen atoms attached to carbon were fixed in geometrically expected positions, with C—H distance 0.96 Å. On the other hand, positions of H atoms of OH groups were refined without any restrain or constrain. ADP of all hydrogen atoms were fixed as 1.2 multiple of the equivalent isotropic ADP of their parent atom
Data collection: CrysAlis PRO (Agilent, 2010); cell
CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: Superflip (Palatinus & Chapuis 2007); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006 (Petříček et al., 2006).C19H24N2O2 | F(000) = 672 |
Mr = 312.4 | Dx = 1.227 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2yn | Cell parameters from 8356 reflections |
a = 11.5029 (4) Å | θ = 4.0–66.9° |
b = 9.5001 (3) Å | µ = 0.63 mm−1 |
c = 16.1874 (6) Å | T = 120 K |
β = 107.078 (3)° | Pyramidal shape, white |
V = 1690.94 (10) Å3 | 0.25 × 0.22 × 0.13 mm |
Z = 4 |
Agilent Xcalibur Atlas Gemini ultra diffractometer | 3007 independent reflections |
Radiation source: Enhance Ultra (Cu) X-ray source | 2648 reflections with I > 3σ(I) |
Mirror monochromator | Rint = 0.021 |
Detector resolution: 10.3784 pixels mm-1 | θmax = 67.1°, θmin = 4.2° |
ω scans | h = −13→12 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | k = −11→11 |
Tmin = 0.573, Tmax = 1 | l = −19→18 |
12982 measured reflections |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.033 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2) |
wR(F2) = 0.104 | (Δ/σ)max = 0.0004 |
S = 1.93 | Δρmax = 0.16 e Å−3 |
3007 reflections | Δρmin = −0.14 e Å−3 |
215 parameters | Extinction correction: B-C type 1 Gaussian isotropic (Becker & Coppens, 1974) |
0 restraints | Extinction coefficient: 1300 (400) |
90 constraints |
C19H24N2O2 | V = 1690.94 (10) Å3 |
Mr = 312.4 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 11.5029 (4) Å | µ = 0.63 mm−1 |
b = 9.5001 (3) Å | T = 120 K |
c = 16.1874 (6) Å | 0.25 × 0.22 × 0.13 mm |
β = 107.078 (3)° |
Agilent Xcalibur Atlas Gemini ultra diffractometer | 3007 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | 2648 reflections with I > 3σ(I) |
Tmin = 0.573, Tmax = 1 | Rint = 0.021 |
12982 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.93 | Δρmax = 0.16 e Å−3 |
3007 reflections | Δρmin = −0.14 e Å−3 |
215 parameters |
Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement. The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.88856 (7) | 0.44965 (9) | 0.06241 (5) | 0.0310 (3) | |
O2 | 0.64693 (7) | 0.76997 (9) | −0.30769 (6) | 0.0290 (3) | |
N1 | 0.76722 (9) | 0.73615 (10) | −0.13993 (6) | 0.0266 (3) | |
N2 | 0.84361 (8) | 0.71755 (10) | 0.00889 (6) | 0.0261 (3) | |
C1 | 0.74585 (10) | 0.70626 (11) | −0.32261 (7) | 0.0251 (3) | |
C2 | 0.82536 (10) | 0.62323 (11) | −0.25869 (7) | 0.0243 (3) | |
C3 | 0.76676 (10) | 0.60644 (12) | 0.12013 (7) | 0.0247 (3) | |
C4 | 0.80273 (10) | 0.47037 (12) | 0.10465 (7) | 0.0267 (4) | |
C5 | 0.92398 (10) | 0.56062 (11) | −0.27747 (7) | 0.0245 (3) | |
C6 | 0.86516 (11) | 0.66039 (12) | −0.41913 (7) | 0.0290 (4) | |
C7 | 0.75212 (11) | 0.35433 (13) | 0.13319 (8) | 0.0313 (4) | |
C8 | 1.05237 (11) | 0.50485 (13) | −0.37565 (8) | 0.0305 (4) | |
C9 | 0.72950 (10) | 0.71770 (12) | −0.06231 (7) | 0.0273 (4) | |
C10 | 0.94551 (10) | 0.57626 (12) | −0.35724 (7) | 0.0261 (4) | |
C11 | 0.80246 (10) | 0.60126 (12) | −0.17246 (7) | 0.0256 (4) | |
C12 | 0.67858 (10) | 0.62103 (12) | 0.16280 (7) | 0.0262 (4) | |
C13 | 0.66608 (11) | 0.37235 (13) | 0.17686 (8) | 0.0315 (4) | |
C14 | 0.91127 (11) | 0.83498 (14) | −0.01388 (8) | 0.0336 (4) | |
C15 | 0.87305 (12) | 0.83398 (13) | −0.11242 (8) | 0.0335 (4) | |
C16 | 0.62725 (10) | 0.50583 (12) | 0.19224 (7) | 0.0280 (4) | |
C17 | 0.76650 (11) | 0.72510 (12) | −0.40199 (8) | 0.0283 (4) | |
C18 | 0.82742 (10) | 0.73307 (12) | 0.09490 (7) | 0.0272 (4) | |
C19 | 0.53567 (12) | 0.52729 (15) | 0.24135 (9) | 0.0374 (4) | |
H1c5 | 0.979186 | 0.504614 | −0.233853 | 0.0294* | |
H1c6 | 0.878406 | 0.67367 | −0.474459 | 0.0348* | |
H1c7 | 0.776818 | 0.261183 | 0.122626 | 0.0375* | |
H1c8 | 1.072127 | 0.552979 | −0.421921 | 0.0366* | |
H2c8 | 1.121122 | 0.507333 | −0.324784 | 0.0366* | |
H3c8 | 1.031868 | 0.408791 | −0.391977 | 0.0366* | |
H1c9 | 0.689835 | 0.628276 | −0.064525 | 0.0327* | |
H2c9 | 0.680476 | 0.796361 | −0.055893 | 0.0327* | |
H1c11 | 0.738473 | 0.533616 | −0.178617 | 0.0307* | |
H2c11 | 0.874835 | 0.565476 | −0.131679 | 0.0307* | |
H1c12 | 0.652179 | 0.713903 | 0.172286 | 0.0315* | |
H1c13 | 0.632626 | 0.291154 | 0.196901 | 0.0378* | |
H1c14 | 0.996946 | 0.816774 | 0.007957 | 0.0403* | |
H2c14 | 0.886032 | 0.921709 | 0.006006 | 0.0403* | |
H1c15 | 0.848056 | 0.926862 | −0.133682 | 0.0402* | |
H2c15 | 0.938576 | 0.798444 | −0.131927 | 0.0402* | |
H1c17 | 0.712548 | 0.782964 | −0.445198 | 0.034* | |
H1c18 | 0.77967 | 0.81553 | 0.09603 | 0.0327* | |
H2c18 | 0.905134 | 0.747643 | 0.136757 | 0.0327* | |
H1c19 | 0.480459 | 0.601158 | 0.21462 | 0.0449* | |
H2c19 | 0.491052 | 0.441692 | 0.240675 | 0.0449* | |
H3c19 | 0.577222 | 0.552689 | 0.300002 | 0.0449* | |
H1 | 0.6668 (13) | 0.7721 (15) | −0.2481 (11) | 0.0348* | |
H2 | 0.8974 (14) | 0.5333 (17) | 0.0373 (10) | 0.0372* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0325 (5) | 0.0315 (5) | 0.0289 (4) | 0.0074 (3) | 0.0088 (3) | −0.0025 (3) |
O2 | 0.0265 (4) | 0.0304 (5) | 0.0291 (5) | 0.0048 (3) | 0.0066 (3) | 0.0029 (3) |
N1 | 0.0280 (5) | 0.0255 (5) | 0.0267 (5) | 0.0009 (4) | 0.0087 (4) | 0.0016 (4) |
N2 | 0.0238 (5) | 0.0292 (5) | 0.0253 (5) | −0.0011 (4) | 0.0073 (4) | −0.0005 (4) |
C1 | 0.0243 (6) | 0.0208 (5) | 0.0284 (6) | −0.0011 (4) | 0.0050 (4) | −0.0012 (4) |
C2 | 0.0246 (5) | 0.0209 (5) | 0.0257 (6) | −0.0031 (4) | 0.0048 (4) | 0.0003 (4) |
C3 | 0.0251 (5) | 0.0261 (6) | 0.0203 (5) | 0.0005 (4) | 0.0026 (4) | −0.0016 (4) |
C4 | 0.0262 (6) | 0.0287 (6) | 0.0216 (5) | 0.0036 (4) | 0.0016 (4) | −0.0029 (4) |
C5 | 0.0243 (5) | 0.0202 (5) | 0.0265 (6) | −0.0012 (4) | 0.0034 (4) | 0.0007 (4) |
C6 | 0.0345 (6) | 0.0273 (6) | 0.0248 (6) | −0.0022 (5) | 0.0081 (5) | −0.0005 (4) |
C7 | 0.0379 (7) | 0.0239 (6) | 0.0273 (6) | 0.0035 (5) | 0.0023 (5) | −0.0017 (5) |
C8 | 0.0311 (6) | 0.0295 (6) | 0.0311 (6) | −0.0002 (5) | 0.0096 (5) | −0.0028 (5) |
C9 | 0.0244 (6) | 0.0298 (6) | 0.0276 (6) | 0.0021 (4) | 0.0075 (5) | 0.0014 (4) |
C10 | 0.0268 (6) | 0.0224 (5) | 0.0281 (6) | −0.0032 (4) | 0.0065 (4) | −0.0020 (4) |
C11 | 0.0246 (5) | 0.0239 (5) | 0.0277 (6) | 0.0007 (4) | 0.0070 (4) | 0.0029 (4) |
C12 | 0.0265 (6) | 0.0245 (6) | 0.0260 (5) | 0.0025 (4) | 0.0050 (4) | −0.0004 (4) |
C13 | 0.0356 (6) | 0.0263 (6) | 0.0291 (6) | −0.0046 (5) | 0.0041 (5) | 0.0024 (5) |
C14 | 0.0305 (6) | 0.0366 (7) | 0.0344 (6) | −0.0081 (5) | 0.0106 (5) | −0.0007 (5) |
C15 | 0.0405 (7) | 0.0263 (6) | 0.0341 (7) | −0.0053 (5) | 0.0114 (5) | 0.0014 (5) |
C16 | 0.0254 (6) | 0.0292 (6) | 0.0260 (6) | −0.0012 (4) | 0.0025 (5) | 0.0023 (5) |
C17 | 0.0315 (6) | 0.0243 (6) | 0.0261 (6) | 0.0006 (4) | 0.0036 (5) | 0.0032 (4) |
C18 | 0.0286 (6) | 0.0266 (6) | 0.0268 (6) | −0.0008 (4) | 0.0086 (5) | −0.0036 (4) |
C19 | 0.0332 (7) | 0.0377 (7) | 0.0435 (7) | 0.0000 (5) | 0.0147 (6) | 0.0070 (5) |
O1—C4 | 1.3701 (16) | C8—C10 | 1.5084 (18) |
O1—H2 | 0.912 (17) | C8—H1c8 | 0.96 |
O2—C1 | 1.3715 (15) | C8—H2c8 | 0.96 |
O2—H1 | 0.923 (17) | C8—H3c8 | 0.96 |
N1—C9 | 1.4552 (17) | C9—H1c9 | 0.96 |
N1—C11 | 1.4863 (15) | C9—H2c9 | 0.96 |
N1—C15 | 1.4919 (15) | C11—H1c11 | 0.96 |
N2—C9 | 1.4707 (13) | C11—H2c11 | 0.96 |
N2—C14 | 1.4678 (17) | C12—C16 | 1.3924 (17) |
N2—C18 | 1.4652 (17) | C12—H1c12 | 0.96 |
C1—C2 | 1.4048 (14) | C13—C16 | 1.3909 (17) |
C1—C17 | 1.3852 (18) | C13—H1c13 | 0.96 |
C2—C5 | 1.3913 (17) | C14—C15 | 1.5250 (17) |
C2—C11 | 1.5091 (18) | C14—H1c14 | 0.96 |
C3—C4 | 1.4022 (16) | C14—H2c14 | 0.96 |
C3—C12 | 1.3917 (18) | C15—H1c15 | 0.96 |
C3—C18 | 1.5061 (17) | C15—H2c15 | 0.96 |
C4—C7 | 1.3876 (18) | C16—C19 | 1.508 (2) |
C5—C10 | 1.3923 (18) | C17—H1c17 | 0.96 |
C5—H1c5 | 0.96 | C18—H1c18 | 0.96 |
C6—C10 | 1.3974 (15) | C18—H2c18 | 0.96 |
C6—C17 | 1.3884 (18) | C19—H1c19 | 0.96 |
C6—H1c6 | 0.96 | C19—H2c19 | 0.96 |
C7—C13 | 1.385 (2) | C19—H3c19 | 0.96 |
C7—H1c7 | 0.96 | ||
C4—O1—H2 | 106.8 (11) | C6—C10—C8 | 121.43 (11) |
C1—O2—H1 | 103.3 (10) | N1—C11—C2 | 110.39 (9) |
C9—N1—C11 | 112.56 (9) | N1—C11—H1c11 | 109.47 |
C9—N1—C15 | 103.97 (9) | N1—C11—H2c11 | 109.47 |
C11—N1—C15 | 111.06 (9) | C2—C11—H1c11 | 109.47 |
C9—N2—C14 | 102.68 (9) | C2—C11—H2c11 | 109.47 |
C9—N2—C18 | 114.29 (9) | H1c11—C11—H2c11 | 108.54 |
C14—N2—C18 | 112.76 (9) | C3—C12—C16 | 122.39 (11) |
O2—C1—C2 | 120.83 (11) | C3—C12—H1c12 | 118.8 |
O2—C1—C17 | 118.92 (9) | C16—C12—H1c12 | 118.81 |
C2—C1—C17 | 120.26 (11) | C7—C13—C16 | 121.26 (12) |
C1—C2—C5 | 118.38 (11) | C7—C13—H1c13 | 119.37 |
C1—C2—C11 | 120.41 (11) | C16—C13—H1c13 | 119.37 |
C5—C2—C11 | 121.20 (9) | N2—C14—C15 | 104.28 (9) |
C4—C3—C12 | 118.48 (11) | N2—C14—H1c14 | 109.47 |
C4—C3—C18 | 120.22 (11) | N2—C14—H2c14 | 109.47 |
C12—C3—C18 | 121.22 (10) | C15—C14—H1c14 | 109.47 |
O1—C4—C3 | 121.02 (11) | C15—C14—H2c14 | 109.47 |
O1—C4—C7 | 119.10 (11) | H1c14—C14—H2c14 | 114.2 |
C3—C4—C7 | 119.88 (12) | N1—C15—C14 | 105.98 (11) |
C2—C5—C10 | 122.38 (9) | N1—C15—H1c15 | 109.47 |
C2—C5—H1c5 | 118.81 | N1—C15—H2c15 | 109.47 |
C10—C5—H1c5 | 118.81 | C14—C15—H1c15 | 109.47 |
C10—C6—C17 | 121.16 (12) | C14—C15—H2c15 | 109.47 |
C10—C6—H1c6 | 119.42 | H1c15—C15—H2c15 | 112.75 |
C17—C6—H1c6 | 119.42 | C12—C16—C13 | 117.69 (12) |
C4—C7—C13 | 120.28 (11) | C12—C16—C19 | 120.40 (11) |
C4—C7—H1c7 | 119.86 | C13—C16—C19 | 121.88 (12) |
C13—C7—H1c7 | 119.86 | C1—C17—C6 | 120.07 (10) |
C10—C8—H1c8 | 109.47 | C1—C17—H1c17 | 119.97 |
C10—C8—H2c8 | 109.47 | C6—C17—H1c17 | 119.97 |
C10—C8—H3c8 | 109.47 | N2—C18—C3 | 112.06 (9) |
H1c8—C8—H2c8 | 109.47 | N2—C18—H1c18 | 109.47 |
H1c8—C8—H3c8 | 109.47 | N2—C18—H2c18 | 109.47 |
H2c8—C8—H3c8 | 109.47 | C3—C18—H1c18 | 109.47 |
N1—C9—N2 | 104.65 (9) | C3—C18—H2c18 | 109.47 |
N1—C9—H1c9 | 109.47 | H1c18—C18—H2c18 | 106.76 |
N1—C9—H2c9 | 109.47 | C16—C19—H1c19 | 109.47 |
N2—C9—H1c9 | 109.47 | C16—C19—H2c19 | 109.47 |
N2—C9—H2c9 | 109.47 | C16—C19—H3c19 | 109.47 |
H1c9—C9—H2c9 | 113.89 | H1c19—C19—H2c19 | 109.47 |
C5—C10—C6 | 117.74 (11) | H1c19—C19—H3c19 | 109.47 |
C5—C10—C8 | 120.83 (9) | H2c19—C19—H3c19 | 109.47 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H2···N2 | 0.912 (17) | 1.869 (16) | 2.6893 (13) | 148.6 (16) |
O2—H1···N1 | 0.923 (17) | 1.825 (15) | 2.6807 (12) | 153.0 (15) |
C17—H1c17···O1i | 0.96 | 2.48 | 3.4286 (14) | 168.38 |
Symmetry code: (i) −x+3/2, y+1/2, −z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H24N2O2 |
Mr | 312.4 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 120 |
a, b, c (Å) | 11.5029 (4), 9.5001 (3), 16.1874 (6) |
β (°) | 107.078 (3) |
V (Å3) | 1690.94 (10) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.63 |
Crystal size (mm) | 0.25 × 0.22 × 0.13 |
Data collection | |
Diffractometer | Agilent Xcalibur Atlas Gemini ultra diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2010) |
Tmin, Tmax | 0.573, 1 |
No. of measured, independent and observed [I > 3σ(I)] reflections | 12982, 3007, 2648 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.104, 1.93 |
No. of reflections | 3007 |
No. of parameters | 215 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.14 |
Computer programs: CrysAlis PRO (Agilent, 2010), Superflip (Palatinus & Chapuis 2007), JANA2006 (Petříček et al., 2006), DIAMOND (Brandenburg & Putz, 2005).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H2···N2 | 0.912 (17) | 1.869 (16) | 2.6893 (13) | 148.6 (16) |
O2—H1···N1 | 0.923 (17) | 1.825 (15) | 2.6807 (12) | 153.0 (15) |
C17—H1c17···O1i | 0.96 | 2.48 | 3.4286 (14) | 168.38 |
Symmetry code: (i) −x+3/2, y+1/2, −z−1/2. |
Acknowledgements
We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia, for financial support of this work as well as the Praemium Academiae project of the Academy of Sciences of the Czech Republic. LSN thanks COLCIENCIAS for a fellowship.
References
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The 1,3-imidazolidine system is intriguing because it is present in biologically active molecules with anti-inflammatory and analgesic properties (Sharma et al., 2001). In our current investigations of factors which influence intramolecular hydrogen bond strength in 1,3-imidazolidine-bridged bis(phenols) (Rivera et al., 2011, 2012), we turn our attention to title compound (I) because the methyl substituent at the para-position in aromatic rings is an electron-donating group which makes the negative charge of hydroxyl group.
The molecular structure and atom-numbering scheme for (I) are shown in Fig. 1 The imidazolidine ring adopts a twist conformation, with twist about the C9—N2 bond; the puckering parameters (Cremer & Pople, 1975), Q2 = 0.4008 (13) Å and ϕ2 = 51.81 (18)°. Intraanular bond lengths (Allen et al., 1987) and angles of (I) are within normal ranges and are comparable to similar structures (Rivera et al., 2011, 2012). The mean plane of imidazolidine ring defined by N1, C15 and C14 makes a dihedral angle of 72.375 (85)° and 71.644 (96)° with the two pendant aromatic rings, C1/C2/C5/C10/C6/C17 and C3/C4/C7/C13/C16/C12 respectively. The dihedral angle between the phenyl rings is 55.938 (83)°. Its X-ray structure confirms the presence of intramolecular hydrogen bonds between the phenolic hydroxyl groups and nitrogen atoms with graph-set motif S(6) (Bernstein et al., 1995) (Table 1). The observed N···O distances [2.6807 (12) Å and 2.6893 (13) Å] and the observed C–O bond lengths [1.3701 (16) Å and 1.3715 (15) Å] are longer in relation to the unsubstituted related structures [2.6557 (13) Å and 1.3654 (15) Å, respectively] (Rivera et al., 2012) and p-chloro derivative [2.6524 (17) Å and 1.366 (2) Å, respectively] (Rivera et al., 2011). This result could indicate that the electro-donating nature of the methyl group at para-position influences the strength of the intra-molecular hydrogen bond.
In the crystal, intermolecular C—H···O hydrogen bonds lead to the formation of chains along the b axis, (Table 1, Fig. 2).