organic compounds
1,3-Dibenzyl-2-(2-chlorophenyl)-4-methylimidazolidine
aUniversidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No. 45-03, Bogotá, Código Postal 111321, Colombia, bDepartment of Solid State Chemistry, Institute of Chemical Technology, Technická 5, 166 28 Prague, Czech Republic, and cInstitute of Physics AS CR, v.v.i., Na Slovance 2, 182 21 Prague 8, Czech Republic
*Correspondence e-mail: ariverau@unal.edu.co
In the title compound, C24H25ClN2, the methine, methylene and methyl C atoms of the methyl-substituted imidazolidine ring are disordered over two sets of sites with a refined occupancy ratio of 0.834 (4):0.166 (4). Each disordered ring assumes an with an N atom as the flap. The pendant benzyl rings are oriented equatorially with respect to the imidazolidine ring. The chlorophenyl ring is inclined to the mean plane of the four planar atoms of the major component of the imidazolidine ring by 76.27 (12)°. The dihedral angles between the chlorophenyl ring and the two benzyl rings are 55.31 (9) and 57.50 (8)°; the dihedral angle between these latter rings is 71.59 (9)°. In the crystal, molecules are linked by C—H⋯Cl interactions and a number of weak C—H⋯π interactions, involving all three aromatic rings, forming a three-dimensional structure.
Related literature
For uses of imidazolidine-bridged bis(phenol) derivatives in coordination chemistry, see: Xu et al. (2007). For related structures, see: Yang et al. (2009); Xia et al. (2007). For standard bond lengths, see: Allen et al. (1987). For ring conformations, see: Cremer & Pople (1975).
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/S1600536812047575/su2527sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812047575/su2527Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812047575/su2527Isup3.cml
A toluene solution of N1,N2-dibenzylpropane-1,2-diamine was refluxed for 8 h with 4-chlorobenzaldehyde in a molar ratio of 1.1:1.0. The mixture was evaporated on a rotary evaporator. The residue was cooled, and the precipitate was filtered off. It was then washed with cold ethanol, dried in air, and recrystallized from ethanol [Yield 81%; M.p. 352-353 K].
H atoms present in the structural model were discernible in difference Fourier maps and could be refined to reasonable geometry. According to common practice H atoms bonded to C were kept in ideal positions with C–H = 0.96 Å and Uiso(H) = 1.2Ueq(C,N). The methine, methylene and methyl groups of the methyl substituted imidazolidine ring were found to be disordered with a refined occupancy ratio of 0.834 (4):0.166 (4). The disordered part of the molecule was refined with bond distances of both fractions kept at the same values. The H atoms of the minor fraction could also be found in difference Fourier maps as faint maxima, however, their addition had negligible impact on R values and GOF. Moreover, it was found that the refined geometry of the minor fraction C atoms is not sufficiently correct for derivation of proper H atom positions, as indicated by too close positions between H2C25' and H2C7 (1.81Å). However, these H atoms were retained in the final refined structural model.
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).Fig. 1. A view of the molecular structure of the title compound, showing the atom numbering. Displacement ellipsoids are drawn at the 50% probability level. Only the major component of the disordered methyl substitued imidazolidine ring is shown. |
C24H25ClN2 | Z = 4 |
Mr = 376.9 | F(000) = 800 |
Monoclinic, P21/c | Dx = 1.213 Mg m−3 |
Hall symbol: -P 2ycb | Cu Kα radiation, λ = 1.5418 Å |
a = 7.1858 (1) Å | Cell parameters from 20478 reflections |
b = 9.8577 (2) Å | θ = 3.0–67.0° |
c = 29.3310 (5) Å | µ = 1.70 mm−1 |
β = 96.8591 (15)° | T = 120 K |
V = 2062.80 (6) Å3 | 0.44 × 0.32 × 0.21 mm |
Agilent Xcalibur (Atlas, Gemini ultra) diffractometer | 3665 independent reflections |
Radiation source: Enhance Ultra (Cu) X-ray Source | 3464 reflections with I > 3σ(I) |
Mirror monochromator | Rint = 0.029 |
Detector resolution: 10.3784 pixels mm-1 | θmax = 67.1°, θmin = 3.0° |
ω scans | h = −8→8 |
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010) | k = −11→11 |
Tmin = 0.62, Tmax = 0.751 | l = −34→34 |
39415 measured reflections |
Refinement on F2 | 153 constraints |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.144 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2) |
S = 2.91 | (Δ/σ)max = 0.047 |
3665 reflections | Δρmax = 0.24 e Å−3 |
260 parameters | Δρmin = −0.35 e Å−3 |
4 restraints |
C24H25ClN2 | V = 2062.80 (6) Å3 |
Mr = 376.9 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 7.1858 (1) Å | µ = 1.70 mm−1 |
b = 9.8577 (2) Å | T = 120 K |
c = 29.3310 (5) Å | 0.44 × 0.32 × 0.21 mm |
β = 96.8591 (15)° |
Agilent Xcalibur (Atlas, Gemini ultra) diffractometer | 3665 independent reflections |
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010) | 3464 reflections with I > 3σ(I) |
Tmin = 0.62, Tmax = 0.751 | Rint = 0.029 |
39415 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 4 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 2.91 | Δρmax = 0.24 e Å−3 |
3665 reflections | Δρmin = −0.35 e Å−3 |
260 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl24 | −0.02857 (6) | −0.36115 (5) | 0.065592 (15) | 0.04745 (17) | |
N8 | 0.1847 (2) | −0.10600 (13) | 0.17251 (5) | 0.0361 (4) | |
N10 | 0.3151 (2) | −0.02081 (12) | 0.11112 (5) | 0.0344 (4) | |
C16 | 0.7452 (3) | 0.2032 (2) | 0.05130 (6) | 0.0477 (6) | |
C20 | 0.5614 (3) | −0.41315 (17) | 0.13435 (6) | 0.0424 (6) | |
C2 | 0.1697 (3) | −0.20165 (19) | 0.31553 (7) | 0.0497 (6) | |
C19 | 0.4692 (2) | −0.29057 (17) | 0.13876 (6) | 0.0391 (5) | |
C15 | 0.6776 (3) | 0.30121 (19) | 0.01963 (6) | 0.0452 (6) | |
C17 | 0.6261 (3) | 0.10445 (18) | 0.06521 (6) | 0.0448 (6) | |
C21 | 0.4719 (3) | −0.51645 (17) | 0.10812 (6) | 0.0427 (6) | |
C1 | 0.1636 (3) | −0.21435 (18) | 0.26802 (6) | 0.0432 (6) | |
C3 | 0.0314 (3) | −0.13050 (19) | 0.33373 (7) | 0.0553 (7) | |
C23 | 0.2014 (2) | −0.37547 (16) | 0.09207 (6) | 0.0349 (5) | |
C22 | 0.2929 (3) | −0.49840 (16) | 0.08697 (6) | 0.0399 (5) | |
C18 | 0.2879 (2) | −0.26912 (15) | 0.11737 (5) | 0.0324 (5) | |
C11 | 0.3064 (3) | −0.00554 (16) | 0.06139 (6) | 0.0390 (5) | |
C6 | 0.0205 (3) | −0.15668 (17) | 0.23914 (6) | 0.0406 (6) | |
C12 | 0.4379 (3) | 0.10288 (16) | 0.04778 (5) | 0.0362 (5) | |
C9 | 0.1973 (2) | −0.13226 (15) | 0.12385 (6) | 0.0340 (5) | |
C14 | 0.4925 (3) | 0.29944 (18) | 0.00181 (6) | 0.0446 (6) | |
C13 | 0.3724 (3) | 0.20095 (16) | 0.01582 (6) | 0.0398 (5) | |
C7 | 0.0183 (2) | −0.1681 (2) | 0.18783 (6) | 0.0434 (6) | |
C25 | 0.2377 (4) | 0.0968 (2) | 0.13284 (8) | 0.0382 (6) | 0.834 (4) |
C26' | 0.2578 (14) | 0.0937 (8) | 0.1408 (4) | 0.0382 (6) | 0.166 (4) |
C4 | −0.1125 (3) | −0.0734 (2) | 0.30561 (8) | 0.0593 (8) | |
C5 | −0.1196 (3) | −0.0859 (2) | 0.25804 (7) | 0.0510 (7) | |
C27 | 0.3731 (3) | 0.0772 (2) | 0.21620 (8) | 0.0475 (7) | 0.834 (4) |
C26 | 0.2097 (3) | 0.04486 (18) | 0.18044 (7) | 0.0349 (7) | 0.834 (4) |
C27' | 0.4362 (15) | 0.1242 (11) | 0.1719 (4) | 0.047 (4) | 0.166 (4) |
C25' | 0.1081 (17) | 0.0315 (6) | 0.1670 (4) | 0.0349 (7) | 0.166 (4) |
H1c16 | 0.875012 | 0.203631 | 0.063679 | 0.0573* | |
H1c20 | 0.686283 | −0.426164 | 0.149381 | 0.0509* | |
H1c2 | 0.269944 | −0.242418 | 0.335449 | 0.0596* | |
H1c19 | 0.531872 | −0.21934 | 0.156898 | 0.047* | |
H1c15 | 0.760026 | 0.369776 | 0.01026 | 0.0543* | |
H1c17 | 0.674392 | 0.036817 | 0.087035 | 0.0538* | |
H1c21 | 0.535525 | −0.600857 | 0.104771 | 0.0513* | |
H1c1 | 0.260406 | −0.263872 | 0.255352 | 0.0518* | |
H1c3 | 0.036117 | −0.120936 | 0.366424 | 0.0664* | |
H1c22 | 0.231051 | −0.569829 | 0.068775 | 0.0479* | |
H1c11 | 0.180416 | 0.015881 | 0.048777 | 0.0468* | |
H2c11 | 0.336042 | −0.090551 | 0.04801 | 0.0468* | |
H1c9 | 0.077614 | −0.135976 | 0.105426 | 0.0408* | |
H1c14 | 0.445321 | 0.366312 | −0.020417 | 0.0535* | |
H1c13 | 0.242801 | 0.200852 | 0.003238 | 0.0478* | |
H1c7 | 0.01236 | −0.26198 | 0.179091 | 0.0521* | |
H2c7 | −0.092009 | −0.124555 | 0.172859 | 0.0521* | |
H1c4 | −0.209051 | −0.024474 | 0.318574 | 0.0711* | |
H1c5 | −0.221036 | −0.045807 | 0.238336 | 0.0612* | |
H1c25 | 0.328399 | 0.168788 | 0.135627 | 0.0458* | 0.834 (4) |
H2c25 | 0.118473 | 0.120137 | 0.116385 | 0.0458* | 0.834 (4) |
H1c27 | 0.487331 | 0.046259 | 0.205703 | 0.057* | 0.834 (4) |
H2c27 | 0.379789 | 0.173462 | 0.221124 | 0.057* | 0.834 (4) |
H3c27 | 0.356064 | 0.032474 | 0.244474 | 0.057* | 0.834 (4) |
H1c26 | 0.105513 | 0.086723 | 0.192608 | 0.0419* | 0.834 (4) |
H1c26' | 0.209453 | 0.174743 | 0.125584 | 0.0458* | 0.166 (4) |
H1c25' | 0.111895 | 0.073924 | 0.196512 | 0.0419* | 0.166 (4) |
H2c25' | −0.009138 | 0.028882 | 0.147483 | 0.0419* | 0.166 (4) |
H1c27' | 0.497636 | 0.040672 | 0.181514 | 0.0568* | 0.166 (4) |
H2c27' | 0.517824 | 0.178023 | 0.155616 | 0.0568* | 0.166 (4) |
H3c27' | 0.406452 | 0.173148 | 0.198402 | 0.0568* | 0.166 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl24 | 0.0489 (3) | 0.0456 (3) | 0.0467 (3) | 0.00039 (17) | 0.0010 (2) | −0.00135 (17) |
N8 | 0.0483 (8) | 0.0258 (7) | 0.0366 (7) | 0.0073 (5) | 0.0153 (6) | 0.0017 (5) |
N10 | 0.0490 (8) | 0.0239 (6) | 0.0314 (7) | 0.0070 (5) | 0.0101 (6) | 0.0025 (5) |
C16 | 0.0496 (10) | 0.0535 (11) | 0.0411 (10) | 0.0026 (8) | 0.0098 (8) | −0.0068 (8) |
C20 | 0.0465 (10) | 0.0350 (9) | 0.0471 (10) | 0.0140 (7) | 0.0113 (8) | 0.0070 (7) |
C2 | 0.0659 (12) | 0.0420 (10) | 0.0414 (10) | −0.0193 (9) | 0.0072 (9) | 0.0011 (8) |
C19 | 0.0453 (9) | 0.0294 (8) | 0.0434 (9) | 0.0075 (7) | 0.0082 (8) | 0.0015 (7) |
C15 | 0.0613 (11) | 0.0405 (9) | 0.0372 (9) | −0.0035 (8) | 0.0201 (8) | −0.0063 (7) |
C17 | 0.0572 (11) | 0.0400 (9) | 0.0379 (9) | 0.0119 (8) | 0.0081 (8) | 0.0038 (7) |
C21 | 0.0600 (11) | 0.0303 (8) | 0.0416 (9) | 0.0145 (7) | 0.0213 (9) | 0.0054 (7) |
C1 | 0.0512 (10) | 0.0357 (9) | 0.0437 (10) | −0.0076 (7) | 0.0101 (8) | −0.0007 (7) |
C3 | 0.0879 (16) | 0.0390 (10) | 0.0423 (11) | −0.0265 (10) | 0.0210 (11) | −0.0051 (8) |
C23 | 0.0434 (9) | 0.0314 (8) | 0.0315 (8) | 0.0037 (6) | 0.0114 (7) | 0.0047 (6) |
C22 | 0.0612 (11) | 0.0268 (8) | 0.0346 (9) | 0.0023 (7) | 0.0178 (8) | 0.0006 (6) |
C18 | 0.0436 (9) | 0.0244 (7) | 0.0310 (7) | 0.0061 (6) | 0.0119 (7) | 0.0032 (6) |
C11 | 0.0563 (10) | 0.0289 (8) | 0.0328 (8) | 0.0049 (7) | 0.0090 (8) | 0.0008 (6) |
C6 | 0.0492 (10) | 0.0338 (9) | 0.0416 (10) | −0.0023 (7) | 0.0175 (8) | 0.0007 (7) |
C12 | 0.0541 (10) | 0.0270 (8) | 0.0290 (8) | 0.0070 (7) | 0.0111 (7) | −0.0011 (6) |
C9 | 0.0408 (9) | 0.0265 (8) | 0.0351 (9) | 0.0083 (6) | 0.0069 (7) | 0.0022 (6) |
C14 | 0.0663 (12) | 0.0326 (9) | 0.0368 (9) | 0.0053 (8) | 0.0142 (8) | 0.0040 (7) |
C13 | 0.0532 (10) | 0.0331 (8) | 0.0342 (8) | 0.0067 (7) | 0.0093 (8) | 0.0025 (7) |
C7 | 0.0403 (9) | 0.0503 (10) | 0.0409 (10) | 0.0051 (7) | 0.0099 (8) | 0.0029 (8) |
C25 | 0.0524 (11) | 0.0271 (8) | 0.0357 (11) | 0.0063 (7) | 0.0082 (9) | −0.0031 (8) |
C26' | 0.0524 (11) | 0.0271 (8) | 0.0357 (11) | 0.0063 (7) | 0.0082 (9) | −0.0031 (8) |
C4 | 0.0835 (15) | 0.0404 (10) | 0.0624 (13) | −0.0097 (10) | 0.0439 (12) | −0.0095 (9) |
C5 | 0.0574 (12) | 0.0454 (10) | 0.0544 (11) | 0.0045 (8) | 0.0241 (10) | 0.0034 (9) |
C27 | 0.0632 (14) | 0.0351 (11) | 0.0427 (12) | −0.0055 (10) | 0.0004 (10) | 0.0021 (9) |
C26 | 0.0446 (14) | 0.0231 (8) | 0.0384 (11) | 0.0061 (8) | 0.0109 (10) | −0.0018 (7) |
C27' | 0.044 (6) | 0.042 (6) | 0.056 (7) | −0.006 (4) | 0.007 (5) | −0.018 (5) |
C25' | 0.0446 (14) | 0.0231 (8) | 0.0384 (11) | 0.0061 (8) | 0.0109 (10) | −0.0018 (7) |
N8—C9 | 1.464 (2) | C18—C9 | 1.520 (2) |
N8—C7 | 1.461 (2) | C11—C12 | 1.511 (2) |
N8—C26 | 1.513 (2) | C11—H1c11 | 0.96 |
N8—C25' | 1.464 (7) | C11—H2c11 | 0.96 |
N10—C11 | 1.460 (2) | C6—C7 | 1.507 (3) |
N10—C9 | 1.462 (2) | C6—C5 | 1.393 (3) |
N10—C25 | 1.464 (3) | C12—C13 | 1.389 (2) |
N10—C26' | 1.512 (10) | C9—H1c9 | 0.96 |
C16—C15 | 1.387 (3) | C14—C13 | 1.393 (3) |
C16—C17 | 1.389 (3) | C14—H1c14 | 0.96 |
C16—H1c16 | 0.96 | C13—H1c13 | 0.96 |
C20—C19 | 1.391 (2) | C7—H1c7 | 0.96 |
C20—C21 | 1.387 (2) | C7—H2c7 | 0.96 |
C20—H1c20 | 0.96 | C25—C26 | 1.523 (3) |
C2—C1 | 1.395 (3) | C25—H1c25 | 0.96 |
C2—C3 | 1.375 (3) | C25—H2c25 | 0.96 |
C2—H1c2 | 0.96 | C26'—C27' | 1.512 (14) |
C19—C18 | 1.393 (2) | C26'—C25' | 1.523 (16) |
C19—H1c19 | 0.96 | C26'—H1c26' | 0.96 |
C15—C14 | 1.370 (3) | C4—C5 | 1.395 (3) |
C15—H1c15 | 0.96 | C4—H1c4 | 0.96 |
C17—C12 | 1.388 (3) | C5—H1c5 | 0.96 |
C17—H1c17 | 0.96 | C27—C26 | 1.512 (3) |
C21—C22 | 1.371 (3) | C27—H1c27 | 0.96 |
C21—H1c21 | 0.96 | C27—H2c27 | 0.96 |
C1—C6 | 1.375 (2) | C27—H3c27 | 0.96 |
C1—H1c1 | 0.96 | C26—H1c26 | 0.96 |
C3—C4 | 1.365 (3) | C27'—H1c27' | 0.96 |
C3—H1c3 | 0.96 | C27'—H2c27' | 0.96 |
C23—C22 | 1.395 (2) | C27'—H3c27' | 0.96 |
C23—C18 | 1.388 (2) | C25'—H1c25' | 0.96 |
C22—H1c22 | 0.96 | C25'—H2c25' | 0.96 |
C9—N8—C7 | 111.94 (13) | N8—C9—H1c9 | 113.6 |
C9—N8—C26 | 107.69 (13) | N10—C9—C18 | 111.41 (14) |
C9—N8—C25' | 97.0 (5) | N10—C9—H1c9 | 113.07 |
C7—N8—C26 | 116.80 (15) | C18—C9—H1c9 | 105.31 |
C7—N8—C25' | 96.4 (5) | C15—C14—C13 | 120.25 (16) |
C11—N10—C9 | 112.07 (12) | C15—C14—H1c14 | 119.88 |
C11—N10—C25 | 112.33 (14) | C13—C14—H1c14 | 119.88 |
C11—N10—C26' | 121.1 (4) | C12—C13—C14 | 120.82 (17) |
C9—N10—C25 | 102.85 (15) | C12—C13—H1c13 | 119.59 |
C9—N10—C26' | 102.0 (4) | C14—C13—H1c13 | 119.59 |
C15—C16—C17 | 120.43 (18) | N8—C7—C6 | 111.35 (14) |
C15—C16—H1c16 | 119.79 | N8—C7—H1c7 | 109.47 |
C17—C16—H1c16 | 119.78 | N8—C7—H2c7 | 109.47 |
C19—C20—C21 | 119.66 (16) | C6—C7—H1c7 | 109.47 |
C19—C20—H1c20 | 120.17 | C6—C7—H2c7 | 109.47 |
C21—C20—H1c20 | 120.17 | H1c7—C7—H2c7 | 107.53 |
C1—C2—C3 | 119.75 (18) | N10—C25—C26 | 103.37 (16) |
C1—C2—H1c2 | 120.13 | N10—C25—H1c25 | 109.47 |
C3—C2—H1c2 | 120.13 | N10—C25—H2c25 | 109.47 |
C20—C19—C18 | 121.33 (15) | C26—C25—H1c25 | 109.47 |
C20—C19—H1c19 | 119.33 | C26—C25—H2c25 | 109.47 |
C18—C19—H1c19 | 119.33 | H1c25—C25—H2c25 | 114.95 |
C16—C15—C14 | 119.51 (18) | N10—C26'—C27' | 103.1 (7) |
C16—C15—H1c15 | 120.24 | N10—C26'—C25' | 104.3 (6) |
C14—C15—H1c15 | 120.25 | N10—C26'—H1c26' | 117.48 |
C16—C17—C12 | 120.46 (16) | C27'—C26'—C25' | 112.0 (9) |
C16—C17—H1c17 | 119.77 | C27'—C26'—H1c26' | 110.43 |
C12—C17—H1c17 | 119.77 | C25'—C26'—H1c26' | 109.35 |
C20—C21—C22 | 120.22 (16) | C3—C4—C5 | 120.1 (2) |
C20—C21—H1c21 | 119.89 | C3—C4—H1c4 | 119.92 |
C22—C21—H1c21 | 119.89 | C5—C4—H1c4 | 119.93 |
C2—C1—C6 | 120.67 (18) | C6—C5—C4 | 120.03 (19) |
C2—C1—H1c1 | 119.66 | C6—C5—H1c5 | 119.98 |
C6—C1—H1c1 | 119.66 | C4—C5—H1c5 | 119.98 |
C2—C3—C4 | 120.4 (2) | C26—C27—H1c27 | 109.47 |
C2—C3—H1c3 | 119.8 | C26—C27—H2c27 | 109.47 |
C4—C3—H1c3 | 119.8 | C26—C27—H3c27 | 109.47 |
C22—C23—C18 | 121.77 (15) | H1c27—C27—H2c27 | 109.47 |
C21—C22—C23 | 119.53 (15) | H1c27—C27—H3c27 | 109.47 |
C21—C22—H1c22 | 120.23 | H2c27—C27—H3c27 | 109.47 |
C23—C22—H1c22 | 120.24 | N8—C26—C25 | 102.47 (15) |
C19—C18—C23 | 117.47 (14) | N8—C26—C27 | 112.46 (16) |
C19—C18—C9 | 118.05 (13) | N8—C26—H1c26 | 113.36 |
C23—C18—C9 | 124.48 (14) | C25—C26—C27 | 112.82 (19) |
N10—C11—C12 | 112.54 (13) | C25—C26—H1c26 | 113 |
N10—C11—H1c11 | 109.47 | C27—C26—H1c26 | 103.12 |
N10—C11—H2c11 | 109.47 | C26'—C27'—H1c27' | 109.47 |
C12—C11—H1c11 | 109.47 | C26'—C27'—H2c27' | 109.47 |
C12—C11—H2c11 | 109.47 | C26'—C27'—H3c27' | 109.47 |
H1c11—C11—H2c11 | 106.21 | H1c27'—C27'—H2c27' | 109.47 |
C1—C6—C7 | 120.16 (17) | H1c27'—C27'—H3c27' | 109.47 |
C1—C6—C5 | 119.00 (18) | H2c27'—C27'—H3c27' | 109.47 |
C7—C6—C5 | 120.83 (16) | N8—C25'—C26' | 98.6 (8) |
C17—C12—C11 | 121.54 (15) | N8—C25'—H1c25' | 109.47 |
C17—C12—C13 | 118.53 (16) | N8—C25'—H2c25' | 109.47 |
C11—C12—C13 | 119.89 (15) | C26'—C25'—H1c25' | 109.47 |
N8—C9—N10 | 102.77 (12) | C26'—C25'—H2c25' | 109.47 |
N8—C9—C18 | 110.86 (12) | H1c25'—C25'—H2c25' | 118.51 |
Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C12–C17 and C18–C23 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H1C9···Cl24 | 0.96 | 2.58 | 3.1596 (16) | 119 |
C21—H1c21···Cg2i | 0.96 | 2.87 | 3.6324 (19) | 137 |
C11—H2c11···Cg2ii | 0.96 | 2.82 | 3.6192 (19) | 142 |
C4—H1c4···Cg3iii | 0.96 | 2.79 | 3.695 (2) | 157 |
C26—H1c26···Cg1iii | 0.96 | 2.91 | 3.688 (2) | 139 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y, −z; (iii) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C24H25ClN2 |
Mr | 376.9 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 120 |
a, b, c (Å) | 7.1858 (1), 9.8577 (2), 29.3310 (5) |
β (°) | 96.8591 (15) |
V (Å3) | 2062.80 (6) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 1.70 |
Crystal size (mm) | 0.44 × 0.32 × 0.21 |
Data collection | |
Diffractometer | Agilent Xcalibur (Atlas, Gemini ultra) diffractometer |
Absorption correction | Analytical (CrysAlis PRO; Agilent, 2010) |
Tmin, Tmax | 0.62, 0.751 |
No. of measured, independent and observed [I > 3σ(I)] reflections | 39415, 3665, 3464 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.598 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.144, 2.91 |
No. of reflections | 3665 |
No. of parameters | 260 |
No. of restraints | 4 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.35 |
Computer programs: CrysAlis PRO (Agilent, 2010), SUPERFLIP (Palatinus & Chapuis, 2007), JANA2006 (Petříček et al., 2006), DIAMOND (Brandenburg & Putz, 2005).
Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C12–C17 and C18–C23 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H1C9···Cl24 | 0.96 | 2.58 | 3.1596 (16) | 119 |
C21—H1c21···Cg2i | 0.96 | 2.87 | 3.6324 (19) | 137 |
C11—H2c11···Cg2ii | 0.96 | 2.82 | 3.6192 (19) | 142 |
C4—H1c4···Cg3iii | 0.96 | 2.79 | 3.695 (2) | 157 |
C26—H1c26···Cg1iii | 0.96 | 2.91 | 3.688 (2) | 139 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y, −z; (iii) −x, 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 Institutional research plan (No. AVOZ10100521) of the Institute of Physics. VE and MD acknowledge the suport provided by the project Praemium Academiae of the Academy of Sciences (ASCR), Czech Republic.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As part of our studies on the synthesis of new imidazolidine derivatives we have prepared the title compound. It is an imidazolidine-bridged bis(phenol) which can serve as a useful precursor for the synthesis of lanthanide complexes of great potential application in homogeneous catalysis (Xu et al., 2007), and herein we report on its crystal structure.
In the title compound, Fig. 1, the methyl substituted imidazolidine ring exhibits molecular disorder over two orientations, with a refined occupancy ratio of 0.834 (4):0.166 (4) for atoms (C25,C26,C27):(C25',C26',C27'). The bond lengths (Allen et al., 1987) and angles are close to normal. In the imidazolidine ring, the bond lengths and angles are similar to those reported for closely related structures (Yang et al., 2009; Xia et al., 2007).
Each disordered component of the imidazolidine ring [N8/C9/N10/C25(25')/C26(26')] adopts an envelope conformation on N10 (major component) and N8 (minor component), respectively, with puckering parameters of Q2 = 0.427 (2) Å and ϕ2 = 252.5 (3)° for the major component, and Q2 = 0.555 (6) Å and ϕ2 = 178.7 (8)° for the minor component [Cremer & Pople, 1975].
The chlorophenyl ring attached to C9 (C18—C23) is inclined to the mean plane of the four planar atoms of the major component of the imidazolidine ring by 76.27 (12) °. The dihedral angles between the chlorophenyl ring (C18–C23) and the two benzyl rings (C1-C6) and (C12-C17) are 55.31 (9) and 57.50 (8)°, respectively. The pendant phenyl rings of the benzyl groups are oriented equatorially to the imidazolidine ring. The dihedral angle between these rings is 71.59 (9)°.
In the crystal, molecules are linked by C-H···Cl interactions and a number of weak C—H···π interactions, involving all three aromatic rings (Table 1), forming a three-dimensional structure.