organic compounds
6,6′-Dimethyl-2,2′-[imidazolidine-1,3-diylbis(methylene)]diphenol
aDepartamento de Química, Facultad de Ciencias, Universidad Nacional de Colombia, Sede Bogotá, Cra 30 No. 45-03, Bogotá, Colombia, and bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
*Correspondence e-mail: ariverau@unal.edu.co
In the title compound, C19H24N2O2, a di-Mannich base derived from 2-methylphenol and 1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane, the imidazolidine ring adopts a twist conformation, with a twist about the ring N—C bond [C—N—C—C torsion angle = −44.34 (14)°]. The two 2-hydroxy-3-methylbenzyl groups are located in trans positions with respect to the imidazolidine fragment. The structure displays two intramolecular O—H⋯N hydrogen bonds, which each form an S(6) ring motif. In the crystal, the molecules are linked by weak C—H⋯O interactions with a bifurcated acceptor, forming a three-dimensional network.
CCDC reference: 984201
Related literature
For the original synthesis of the title compound, see: Rivera et al. (1993). For related structures, see: Rivera et al. (2011, 2012a,b,c, 2013). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see Cremer & Pople (1975). For bifurcated-acceptor hydrogen-bond conformations, see: Desiraju & Steiner (1999).
Experimental
Crystal data
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Data collection: X-AREA (Stoe & Cie, 2001); cell X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 984201
10.1107/S1600536814002128/fb2295sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814002128/fb2295Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814002128/fb2295Isup3.cml
For the original synthesis of the title compound, see Rivera et al. (1993). Single crystals in the form of needles that were shorter than 1 mm were obtained by slow evaporation of 0.01 M ethanol solution at room temperature. Melting point: 403-404 K.
All the H atoms were located in the difference
The hydroxyl H atoms were refined freely, however, the H atoms bonded to C atoms were situated into the idealized positions and refined using a riding model approximation. The applied constraints were as follows: Cmethylene—H = 0.99Å, Cmethyl—H = 0.98Å and Caryl—H = 0.95Å. Uiso(Haryl/methylene) = 1.2Ueq(Caryl/methylene) except for Uiso(Hmethyl) = 1.5Ueq(Cmethyl). The methyl groups were allowed to rotate during the by application of the command AFIX 137 (SHELXL97 (Sheldrick, 2008)).Data collection: X-AREA (Stoe & Cie, 2001); cell
X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The title molecule with the atom-numbering scheme·The displacement ellipsoids are shown at the 50% probability level. The hydrogen bonds are drawn as dashed lines. |
C19H24N2O2 | Dx = 1.247 Mg m−3 |
Mr = 312.40 | Melting point = 403–404 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.6271 (11) Å | Cell parameters from 17856 reflections |
b = 13.5780 (9) Å | θ = 3.4–26.3° |
c = 10.1997 (9) Å | µ = 0.08 mm−1 |
β = 107.940 (7)° | T = 173 K |
V = 1663.7 (2) Å3 | Needle, brown |
Z = 4 | 0.33 × 0.13 × 0.12 mm |
F(000) = 672 |
Stoe IPDS II two-circle diffractometer | 3207 independent reflections |
Radiation source: Genix 3D IµS microfocus X-ray source | 2803 reflections with I > 2σ(I) |
Genix 3D multilayer optics monochromator | Rint = 0.072 |
ω scans | θmax = 25.9°, θmin = 3.4° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −15→15 |
Tmin = 0.974, Tmax = 0.990 | k = −16→14 |
16285 measured reflections | l = −12→12 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.053P)2 + 0.4801P] whereP = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3207 reflections | Δρmax = 0.20 e Å−3 |
219 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: difference Fourier map | Extinction coefficient: 0.017 (3) |
C19H24N2O2 | V = 1663.7 (2) Å3 |
Mr = 312.40 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.6271 (11) Å | µ = 0.08 mm−1 |
b = 13.5780 (9) Å | T = 173 K |
c = 10.1997 (9) Å | 0.33 × 0.13 × 0.12 mm |
β = 107.940 (7)° |
Stoe IPDS II two-circle diffractometer | 3207 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 2803 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.990 | Rint = 0.072 |
16285 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.20 e Å−3 |
3207 reflections | Δρmin = −0.17 e Å−3 |
219 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.52432 (9) | 0.10588 (7) | 0.59144 (11) | 0.0354 (3) | |
H1 | 0.460 (2) | 0.1024 (17) | 0.519 (2) | 0.067 (7)* | |
O2 | −0.00181 (8) | 0.17557 (8) | 0.53718 (10) | 0.0326 (3) | |
H2 | 0.047 (2) | 0.1533 (18) | 0.485 (2) | 0.070 (7)* | |
N1 | 0.32247 (9) | 0.16347 (9) | 0.42350 (11) | 0.0268 (3) | |
N2 | 0.16437 (9) | 0.10080 (9) | 0.46722 (12) | 0.0290 (3) | |
C1 | 0.25284 (12) | 0.17521 (11) | 0.51349 (15) | 0.0317 (3) | |
H1A | 0.2207 | 0.2423 | 0.5046 | 0.038* | |
H1B | 0.2969 | 0.1639 | 0.6109 | 0.038* | |
C2 | 0.24302 (12) | 0.13405 (12) | 0.29153 (14) | 0.0344 (3) | |
H2A | 0.2812 | 0.1047 | 0.2295 | 0.041* | |
H2B | 0.1970 | 0.1904 | 0.2447 | 0.041* | |
C3 | 0.17414 (13) | 0.05850 (13) | 0.33757 (15) | 0.0382 (4) | |
H3A | 0.1000 | 0.0505 | 0.2682 | 0.046* | |
H3B | 0.2122 | −0.0062 | 0.3542 | 0.046* | |
C4 | 0.38508 (12) | 0.25297 (11) | 0.41628 (15) | 0.0306 (3) | |
H4A | 0.3329 | 0.3089 | 0.3864 | 0.037* | |
H4B | 0.4247 | 0.2440 | 0.3471 | 0.037* | |
C5 | 0.16693 (12) | 0.02503 (11) | 0.57129 (15) | 0.0314 (3) | |
H5A | 0.2444 | 0.0013 | 0.6112 | 0.038* | |
H5B | 0.1208 | −0.0316 | 0.5255 | 0.038* | |
C11 | 0.46819 (11) | 0.27610 (10) | 0.55457 (15) | 0.0282 (3) | |
C12 | 0.53386 (11) | 0.20167 (10) | 0.63485 (15) | 0.0278 (3) | |
C13 | 0.61017 (11) | 0.22221 (11) | 0.76376 (15) | 0.0311 (3) | |
C14 | 0.62035 (12) | 0.31874 (12) | 0.80964 (17) | 0.0381 (4) | |
H14 | 0.6729 | 0.3341 | 0.8962 | 0.046* | |
C15 | 0.55590 (13) | 0.39346 (12) | 0.73245 (19) | 0.0424 (4) | |
H15 | 0.5636 | 0.4591 | 0.7662 | 0.051* | |
C16 | 0.48010 (12) | 0.37156 (11) | 0.60557 (17) | 0.0356 (3) | |
H16 | 0.4356 | 0.4227 | 0.5526 | 0.043* | |
C17 | 0.67528 (13) | 0.14002 (13) | 0.85113 (17) | 0.0411 (4) | |
H17A | 0.7204 | 0.1664 | 0.9402 | 0.062* | |
H17B | 0.7240 | 0.1097 | 0.8042 | 0.062* | |
H17C | 0.6237 | 0.0904 | 0.8659 | 0.062* | |
C21 | 0.12514 (11) | 0.06119 (10) | 0.68633 (14) | 0.0272 (3) | |
C22 | 0.04162 (11) | 0.13237 (10) | 0.66313 (13) | 0.0261 (3) | |
C23 | −0.00336 (12) | 0.16134 (11) | 0.76666 (15) | 0.0296 (3) | |
C24 | 0.03670 (13) | 0.11608 (11) | 0.89454 (15) | 0.0335 (3) | |
H24 | 0.0066 | 0.1339 | 0.9658 | 0.040* | |
C25 | 0.11964 (14) | 0.04555 (11) | 0.92013 (15) | 0.0368 (4) | |
H25 | 0.1461 | 0.0155 | 1.0084 | 0.044* | |
C26 | 0.16402 (12) | 0.01877 (11) | 0.81681 (15) | 0.0330 (3) | |
H26 | 0.2216 | −0.0291 | 0.8352 | 0.040* | |
C27 | −0.09425 (13) | 0.23731 (12) | 0.73391 (17) | 0.0391 (4) | |
H27A | −0.1177 | 0.2491 | 0.8156 | 0.059* | |
H27B | −0.1578 | 0.2136 | 0.6584 | 0.059* | |
H27C | −0.0665 | 0.2988 | 0.7063 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0403 (6) | 0.0253 (5) | 0.0376 (6) | 0.0031 (4) | 0.0076 (5) | −0.0018 (4) |
O2 | 0.0313 (5) | 0.0376 (6) | 0.0286 (5) | 0.0036 (4) | 0.0090 (4) | 0.0072 (4) |
N1 | 0.0281 (6) | 0.0290 (6) | 0.0252 (6) | −0.0013 (5) | 0.0109 (5) | −0.0026 (4) |
N2 | 0.0299 (6) | 0.0310 (6) | 0.0269 (6) | −0.0058 (5) | 0.0097 (5) | −0.0056 (5) |
C1 | 0.0318 (7) | 0.0343 (8) | 0.0332 (7) | −0.0078 (6) | 0.0163 (6) | −0.0096 (6) |
C2 | 0.0354 (7) | 0.0427 (9) | 0.0262 (7) | −0.0025 (6) | 0.0111 (6) | −0.0060 (6) |
C3 | 0.0414 (8) | 0.0431 (9) | 0.0312 (7) | −0.0104 (7) | 0.0128 (6) | −0.0131 (6) |
C4 | 0.0300 (7) | 0.0311 (7) | 0.0329 (7) | 0.0001 (6) | 0.0130 (6) | 0.0059 (6) |
C5 | 0.0308 (7) | 0.0277 (7) | 0.0350 (8) | −0.0012 (6) | 0.0090 (6) | −0.0020 (6) |
C11 | 0.0241 (6) | 0.0285 (7) | 0.0354 (7) | −0.0028 (5) | 0.0141 (6) | 0.0021 (6) |
C12 | 0.0257 (6) | 0.0264 (7) | 0.0345 (7) | −0.0014 (5) | 0.0142 (6) | 0.0003 (6) |
C13 | 0.0252 (7) | 0.0340 (8) | 0.0361 (7) | −0.0024 (6) | 0.0126 (6) | 0.0007 (6) |
C14 | 0.0295 (7) | 0.0380 (9) | 0.0443 (9) | −0.0083 (6) | 0.0076 (6) | −0.0062 (7) |
C15 | 0.0374 (8) | 0.0278 (8) | 0.0600 (10) | −0.0073 (6) | 0.0119 (7) | −0.0095 (7) |
C16 | 0.0311 (7) | 0.0254 (7) | 0.0507 (9) | −0.0015 (6) | 0.0130 (6) | 0.0026 (6) |
C17 | 0.0380 (8) | 0.0424 (9) | 0.0385 (8) | 0.0014 (7) | 0.0055 (7) | 0.0039 (7) |
C21 | 0.0269 (6) | 0.0237 (7) | 0.0297 (7) | −0.0060 (5) | 0.0068 (5) | −0.0015 (5) |
C22 | 0.0260 (6) | 0.0247 (7) | 0.0261 (6) | −0.0073 (5) | 0.0057 (5) | 0.0007 (5) |
C23 | 0.0292 (7) | 0.0281 (7) | 0.0316 (7) | −0.0076 (5) | 0.0095 (6) | −0.0041 (5) |
C24 | 0.0418 (8) | 0.0325 (8) | 0.0280 (7) | −0.0102 (6) | 0.0137 (6) | −0.0047 (6) |
C25 | 0.0471 (9) | 0.0335 (8) | 0.0259 (7) | −0.0064 (7) | 0.0053 (6) | 0.0045 (6) |
C26 | 0.0333 (7) | 0.0275 (7) | 0.0333 (7) | −0.0018 (6) | 0.0031 (6) | 0.0028 (6) |
C27 | 0.0373 (8) | 0.0414 (9) | 0.0400 (8) | 0.0013 (7) | 0.0140 (7) | −0.0039 (7) |
O1—C12 | 1.3673 (17) | C12—C13 | 1.398 (2) |
O1—H1 | 0.91 (2) | C13—C14 | 1.384 (2) |
O2—C22 | 1.3643 (16) | C13—C17 | 1.505 (2) |
O2—H2 | 0.98 (2) | C14—C15 | 1.384 (2) |
N1—C1 | 1.4622 (17) | C14—H14 | 0.9500 |
N1—C4 | 1.4639 (18) | C15—C16 | 1.384 (2) |
N1—C2 | 1.4650 (18) | C15—H15 | 0.9500 |
N2—C5 | 1.4714 (19) | C16—H16 | 0.9500 |
N2—C1 | 1.4719 (17) | C17—H17A | 0.9800 |
N2—C3 | 1.4813 (18) | C17—H17B | 0.9800 |
C1—H1A | 0.9900 | C17—H17C | 0.9800 |
C1—H1B | 0.9900 | C21—C26 | 1.393 (2) |
C2—C3 | 1.510 (2) | C21—C22 | 1.396 (2) |
C2—H2A | 0.9900 | C22—C23 | 1.401 (2) |
C2—H2B | 0.9900 | C23—C24 | 1.389 (2) |
C3—H3A | 0.9900 | C23—C27 | 1.502 (2) |
C3—H3B | 0.9900 | C24—C25 | 1.383 (2) |
C4—C11 | 1.509 (2) | C24—H24 | 0.9500 |
C4—H4A | 0.9900 | C25—C26 | 1.386 (2) |
C4—H4B | 0.9900 | C25—H25 | 0.9500 |
C5—C21 | 1.509 (2) | C26—H26 | 0.9500 |
C5—H5A | 0.9900 | C27—H27A | 0.9800 |
C5—H5B | 0.9900 | C27—H27B | 0.9800 |
C11—C16 | 1.388 (2) | C27—H27C | 0.9800 |
C11—C12 | 1.400 (2) | ||
C12—O1—H1 | 106.2 (15) | C13—C12—C11 | 121.23 (13) |
C22—O2—H2 | 103.8 (14) | C14—C13—C12 | 118.17 (14) |
C1—N1—C4 | 112.31 (11) | C14—C13—C17 | 121.68 (14) |
C1—N1—C2 | 103.44 (11) | C12—C13—C17 | 120.11 (14) |
C4—N1—C2 | 114.07 (11) | C13—C14—C15 | 121.64 (15) |
C5—N2—C1 | 113.75 (11) | C13—C14—H14 | 119.2 |
C5—N2—C3 | 112.55 (12) | C15—C14—H14 | 119.2 |
C1—N2—C3 | 106.78 (11) | C16—C15—C14 | 119.36 (15) |
N1—C1—N2 | 105.53 (11) | C16—C15—H15 | 120.3 |
N1—C1—H1A | 110.6 | C14—C15—H15 | 120.3 |
N2—C1—H1A | 110.6 | C15—C16—C11 | 121.00 (14) |
N1—C1—H1B | 110.6 | C15—C16—H16 | 119.5 |
N2—C1—H1B | 110.6 | C11—C16—H16 | 119.5 |
H1A—C1—H1B | 108.8 | C13—C17—H17A | 109.5 |
N1—C2—C3 | 101.34 (11) | C13—C17—H17B | 109.5 |
N1—C2—H2A | 111.5 | H17A—C17—H17B | 109.5 |
C3—C2—H2A | 111.5 | C13—C17—H17C | 109.5 |
N1—C2—H2B | 111.5 | H17A—C17—H17C | 109.5 |
C3—C2—H2B | 111.5 | H17B—C17—H17C | 109.5 |
H2A—C2—H2B | 109.3 | C26—C21—C22 | 118.27 (13) |
N2—C3—C2 | 103.21 (12) | C26—C21—C5 | 120.23 (13) |
N2—C3—H3A | 111.1 | C22—C21—C5 | 121.36 (12) |
C2—C3—H3A | 111.1 | O2—C22—C21 | 121.39 (12) |
N2—C3—H3B | 111.1 | O2—C22—C23 | 116.77 (12) |
C2—C3—H3B | 111.1 | C21—C22—C23 | 121.83 (12) |
H3A—C3—H3B | 109.1 | C24—C23—C22 | 117.96 (14) |
N1—C4—C11 | 110.89 (11) | C24—C23—C27 | 123.03 (13) |
N1—C4—H4A | 109.5 | C22—C23—C27 | 118.99 (13) |
C11—C4—H4A | 109.5 | C25—C24—C23 | 121.28 (14) |
N1—C4—H4B | 109.5 | C25—C24—H24 | 119.4 |
C11—C4—H4B | 109.5 | C23—C24—H24 | 119.4 |
H4A—C4—H4B | 108.1 | C24—C25—C26 | 119.87 (13) |
N2—C5—C21 | 113.46 (12) | C24—C25—H25 | 120.1 |
N2—C5—H5A | 108.9 | C26—C25—H25 | 120.1 |
C21—C5—H5A | 108.9 | C25—C26—C21 | 120.79 (14) |
N2—C5—H5B | 108.9 | C25—C26—H26 | 119.6 |
C21—C5—H5B | 108.9 | C21—C26—H26 | 119.6 |
H5A—C5—H5B | 107.7 | C23—C27—H27A | 109.5 |
C16—C11—C12 | 118.60 (13) | C23—C27—H27B | 109.5 |
C16—C11—C4 | 120.58 (13) | H27A—C27—H27B | 109.5 |
C12—C11—C4 | 120.82 (13) | C23—C27—H27C | 109.5 |
O1—C12—C13 | 117.43 (13) | H27A—C27—H27C | 109.5 |
O1—C12—C11 | 121.33 (13) | H27B—C27—H27C | 109.5 |
C4—N1—C1—N2 | 156.96 (11) | C12—C13—C14—C15 | 1.2 (2) |
C2—N1—C1—N2 | 33.51 (15) | C17—C13—C14—C15 | −176.34 (15) |
C5—N2—C1—N1 | 115.88 (13) | C13—C14—C15—C16 | −0.7 (2) |
C3—N2—C1—N1 | −8.89 (15) | C14—C15—C16—C11 | −0.3 (2) |
C1—N1—C2—C3 | −44.34 (14) | C12—C11—C16—C15 | 0.6 (2) |
C4—N1—C2—C3 | −166.63 (12) | C4—C11—C16—C15 | 179.84 (14) |
C5—N2—C3—C2 | −143.72 (12) | N2—C5—C21—C26 | −152.12 (12) |
C1—N2—C3—C2 | −18.22 (16) | N2—C5—C21—C22 | 32.45 (18) |
N1—C2—C3—N2 | 38.30 (15) | C26—C21—C22—O2 | −178.73 (12) |
C1—N1—C4—C11 | 65.00 (15) | C5—C21—C22—O2 | −3.2 (2) |
C2—N1—C4—C11 | −177.72 (11) | C26—C21—C22—C23 | −0.2 (2) |
C1—N2—C5—C21 | 74.79 (14) | C5—C21—C22—C23 | 175.35 (12) |
C3—N2—C5—C21 | −163.60 (11) | O2—C22—C23—C24 | 177.86 (12) |
N1—C4—C11—C16 | −135.44 (13) | C21—C22—C23—C24 | −0.8 (2) |
N1—C4—C11—C12 | 43.76 (17) | O2—C22—C23—C27 | −0.48 (19) |
C16—C11—C12—O1 | 178.67 (13) | C21—C22—C23—C27 | −179.12 (13) |
C4—C11—C12—O1 | −0.5 (2) | C22—C23—C24—C25 | 0.9 (2) |
C16—C11—C12—C13 | −0.1 (2) | C27—C23—C24—C25 | 179.21 (14) |
C4—C11—C12—C13 | −179.28 (12) | C23—C24—C25—C26 | −0.2 (2) |
O1—C12—C13—C14 | −179.60 (13) | C24—C25—C26—C21 | −0.8 (2) |
C11—C12—C13—C14 | −0.8 (2) | C22—C21—C26—C25 | 1.0 (2) |
O1—C12—C13—C17 | −2.0 (2) | C5—C21—C26—C25 | −174.60 (13) |
C11—C12—C13—C17 | 176.75 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.91 (2) | 1.90 (2) | 2.7115 (16) | 146 (2) |
O2—H2···N2 | 0.98 (2) | 1.70 (2) | 2.6202 (16) | 155 (2) |
C5—H5B···O2i | 0.99 | 2.43 | 3.4012 (18) | 167 |
C27—H27A···O2ii | 0.98 | 2.50 | 3.1789 (19) | 126 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.91 (2) | 1.90 (2) | 2.7115 (16) | 146 (2) |
O2—H2···N2 | 0.98 (2) | 1.70 (2) | 2.6202 (16) | 155 (2) |
C5—H5B···O2i | 0.99 | 2.43 | 3.4012 (18) | 167.3 |
C27—H27A···O2ii | 0.98 | 2.50 | 3.1789 (19) | 126.1 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x, −y+1/2, z+1/2. |
Acknowledgements
The authors acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia, for financial support of this work. LSN thanks COLCIENCIAS for a fellowship.
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The title molecule with the atom-numbering scheme is shown in Fig 1. The 2-hydroxy-3-methylbenzyl substituents are arranged in trans configuration with respect to the imidazolidine ring. The imidazolidine ring adopts a twist conformation, with a C1—N1—C2—C3 torsion angle equal to -44.34 (14)° (Cremer & Pople, 1975).
The structure of the title compound shows the presence of two intramolecular O—H···N hydrogen bonds. These bond take part in the S(6) graph set motifs (Bernstein et al., 1995). These motifs occur in the related 2,2'-[imidazolidine-1,3-diylbis(methylene)]diphenol compounds (Rivera et al. 2011, 2012a, b, c, 2013), too. The two intramolecular hydrogen bonds are different in their length (Table 1), although both nitrogen atoms are connected to the same atomic species. In the crystal, the molecules are linked to each other by weak C—H···O interactions (Desiraju & Steiner, 1999) C5—H5B···O2i···H27Aiii—C27iii with a bifurcated acceptor O2i where (i): -x, -y, -z+1; (iii): -x, y-1/2, -z+3/2. (For the hydrogen bonds and interactions, see Table 1.)