Literature DB >> 24109297

2,2'-[(4-Methyl-2-phenyl-imidazolidine-1,3-di-yl)bis-(methyl-ene)]diphenol.

Augusto Rivera¹, Lorena Cárdenas, Jaime Ríos-Motta, Václav Eigner, Michal Dušek.

Abstract

The methyl-substituted imidazolidine ring of the title compound, n class="Chemical">C24H26N2O2, adopts an envelope conformation with the N atom adjacent to the methyl-ene group as the flap. The meth-yl-ethyl-ene fragment in this ring is disordered over two positions with an occupancy ratio of 0.899 (4):0.101 (4). The hy-droxy-benzyl groups are inclined at 71.57 (15) and 69.97 (19)° to the mean plane of major disorder component of the heterocyclic ring with an inter-planar angle between the two hy-droxy-benzyl groups of 66.00 (5)°. The phenyl substit-uent approaches a nearly perpendicular orientation relative to the mean plane of the imidazolidine ring, making a dihedral angle of 75.60 (12)°. This conformation is stabilized by two intra-molecular O-H⋯N bonds, which generate S(6) ring motifs.

Entities: Chemical Disease Gene

Year: 2013 PMID： 24109297 PMCID： PMC3793710 DOI： 10.1107/S1600536813017893

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For related structures, see: Rivera et al. (2012 ▶). For the synthesis of the precursor, see: Rivera et al. (2013 ▶). For bond-length data, see: Allen et al. (1987 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C24H26N2O2 M = 374.5 Monoclinic, a = 16.8974 (8) Å b = 9.4893 (5) Å c = 12.5287 (6) Å β = 92.928 (4)° V = 2006.29 (17) Å3 Z = 4 Cu Kα radiation μ = 0.62 mm−1 T = 120 K 0.35 × 0.25 × 0.09 mm

Data collection

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer Absorption correction: analytical (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.886, T max = 0.952 8259 measured reflections 3491 independent reflections 2704 reflections with I > 3σ(I) R int = 0.03

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.113 S = 1.51 3491 reflections 276 parameters 5 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.25 e Å−3 Δρmin = −0.18 e Å−3 Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: 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: DIAMOn class="Chemical">ND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813017893/sj5339sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017893/sj5339Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813017893/sj5339Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₄H₂₆N₂O₂	F(000) = 800
M_r = 374.5	D_x = 1.239 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ycb	Cell parameters from 3676 reflections
a = 16.8974 (8) Å	θ = 3.5–66.9°
b = 9.4893 (5) Å	µ = 0.62 mm⁻¹
c = 12.5287 (6) Å	T = 120 K
β = 92.928 (4)°	Polygon shape, colorless
V = 2006.29 (17) Å³	0.35 × 0.25 × 0.09 mm
Z = 4

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer	3491 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2704 reflections with I > 3σ(I)
Mirror monochromator	R_int = 0.03
Detector resolution: 10.3784 pixels mm^-1	θ_max = 67.0°, θ_min = 5.2°
ω scans	h = −16→19
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)	k = −11→11
T_min = 0.886, T_max = 0.952	l = −14→12
8259 measured reflections

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.042	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0016I²)
wR(F²) = 0.113	(Δ/σ)_max = 0.049
S = 1.51	Δρ_max = 0.25 e Å⁻³
3491 reflections	Δρ_min = −0.18 e Å⁻³
276 parameters	Extinction correction: B-C type 1 Gaussian isotropic (Becker & Coppens, 1974)
5 restraints	Extinction coefficient: 3200 (500)
151 constraints

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.10968 (7)	0.77621 (13)	0.14452 (10)	0.0335 (4)
O19	0.40788 (9)	1.04207 (16)	0.27300 (11)	0.0460 (5)
N11	0.28125 (8)	0.99956 (14)	0.39327 (11)	0.0262 (4)
N9	0.16113 (8)	0.91720 (14)	0.32755 (11)	0.0262 (4)
C3	−0.01906 (11)	0.84850 (19)	0.08234 (15)	0.0323 (5)
C17	0.49554 (10)	1.2217 (2)	0.33593 (15)	0.0335 (6)
C22	0.33481 (10)	0.58293 (19)	0.28115 (14)	0.0303 (5)
C2	0.03749 (10)	0.83400 (18)	0.16509 (14)	0.0282 (5)
C18	0.43614 (10)	1.12529 (19)	0.35565 (13)	0.0301 (5)
C21	0.29810 (10)	0.71116 (18)	0.29487 (13)	0.0277 (5)
C4	−0.09159 (11)	0.91012 (19)	0.10146 (15)	0.0355 (6)
C16	0.52487 (10)	1.3093 (2)	0.41629 (15)	0.0360 (6)
C13	0.40514 (10)	1.11650 (18)	0.45702 (13)	0.0276 (5)
C25	0.26334 (10)	0.63967 (18)	0.46963 (13)	0.0274 (5)
C10	0.22524 (10)	0.88368 (17)	0.40711 (13)	0.0261 (5)
C20	0.26239 (9)	0.74138 (17)	0.39014 (12)	0.0241 (5)
C12	0.34266 (11)	1.00921 (19)	0.47984 (13)	0.0311 (5)
C14	0.43528 (11)	1.2068 (2)	0.53588 (14)	0.0340 (6)
C7	0.02229 (10)	0.87866 (17)	0.26891 (13)	0.0275 (5)
C28	0.17720 (14)	1.1089 (2)	0.19419 (16)	0.0394 (7)	0.899 (4)
C23	0.33604 (10)	0.48228 (19)	0.36133 (14)	0.0315 (5)
C24	0.29998 (10)	0.51088 (19)	0.45540 (14)	0.0310 (5)
C8	0.08435 (10)	0.86041 (19)	0.35794 (13)	0.0311 (5)
C6	−0.05061 (10)	0.94177 (19)	0.28506 (15)	0.0333 (6)
C5	−0.10736 (11)	0.95685 (19)	0.20251 (15)	0.0357 (6)
C27	0.16255 (12)	1.07345 (19)	0.30988 (16)	0.0280 (6)	0.899 (4)
C26	0.22944 (12)	1.1238 (2)	0.38684 (17)	0.0288 (6)	0.899 (4)
C26'	0.1443 (9)	1.0661 (5)	0.3488 (14)	0.0280 (6)	0.101 (4)
C27'	0.2300 (7)	1.1160 (12)	0.3475 (10)	0.0288 (6)	0.101 (4)
C15	0.49529 (11)	1.3021 (2)	0.51673 (15)	0.0383 (6)
H1c3	−0.008331	0.816175	0.011928	0.0387*
H1c17	0.516222	1.227294	0.266103	0.0402*
H1c22	0.359666	0.563345	0.21556	0.0364*
H1c21	0.29715	0.779845	0.238562	0.0333*
H1c4	−0.130988	0.920237	0.044006	0.0426*
H1c16	0.566013	1.375547	0.402306	0.0432*
H1c25	0.238354	0.658669	0.535225	0.0329*
H1c10	0.207032	0.876559	0.478241	0.0313*
H1c12	0.367021	0.918641	0.490924	0.0373*
H2c12	0.31869	1.033102	0.545288	0.0373*
H1c14	0.414141	1.203482	0.60552	0.0408*
H1c28	0.177434	1.20937	0.185208	0.0473*	0.899 (4)
H2c28	0.227476	1.071195	0.175972	0.0473*	0.899 (4)
H3c28	0.135948	1.068532	0.148357	0.0473*	0.899 (4)
H1c23	0.361769	0.393343	0.351577	0.0378*
H1c24	0.300297	0.441351	0.511081	0.0373*
H1c8	0.06796	0.908229	0.420618	0.0373*
H2c8	0.090006	0.762114	0.374792	0.0373*
H1c6	−0.061615	0.975461	0.35501	0.04*
H1c5	−0.157476	0.9996	0.215351	0.0429*
H1c27	0.113089	1.118473	0.322895	0.0336*	0.899 (4)
H1c26	0.256822	1.200587	0.355095	0.0346*	0.899 (4)
H2c26	0.208953	1.141634	0.455632	0.0346*	0.899 (4)
H1c15	0.516029	1.362475	0.572938	0.046*
C28'	0.2525 (10)	1.162 (2)	0.2369 (11)	0.042 (6)	0.101 (4)
H1o1	0.1465 (13)	0.812 (2)	0.2010 (16)	0.0402*
H1o19	0.3584 (15)	1.002 (2)	0.3010 (17)	0.0552*
H1c26'	0.125922	1.075665	0.419702	0.0336*	0.101 (4)
H2c26'	0.114337	1.105645	0.288888	0.0336*	0.101 (4)
H1c27'	0.237554	1.19909	0.390453	0.0346*	0.101 (4)
H1c28'	0.252753	1.082083	0.190266	0.0509*	0.101 (4)
H2c28'	0.214686	1.230137	0.208928	0.0509*	0.101 (4)
H3c28'	0.304301	1.204201	0.241575	0.0509*	0.101 (4)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0253 (6)	0.0372 (7)	0.0383 (7)	0.0031 (5)	0.0046 (5)	−0.0046 (5)
O19	0.0470 (8)	0.0509 (9)	0.0409 (8)	−0.0076 (7)	0.0101 (7)	−0.0169 (6)
N11	0.0290 (7)	0.0204 (7)	0.0290 (7)	−0.0013 (6)	−0.0014 (6)	0.0009 (6)
N9	0.0251 (7)	0.0219 (7)	0.0314 (7)	−0.0004 (6)	0.0008 (6)	0.0031 (6)
C3	0.0309 (9)	0.0308 (9)	0.0353 (9)	−0.0024 (7)	0.0035 (7)	0.0023 (7)
C17	0.0241 (8)	0.0393 (11)	0.0373 (10)	0.0043 (8)	0.0043 (7)	0.0022 (8)
C22	0.0260 (8)	0.0305 (9)	0.0348 (9)	−0.0043 (7)	0.0045 (7)	−0.0092 (7)
C2	0.0250 (8)	0.0234 (8)	0.0366 (9)	−0.0016 (7)	0.0048 (7)	0.0012 (7)
C18	0.0269 (8)	0.0295 (9)	0.0336 (9)	0.0071 (7)	−0.0008 (7)	−0.0054 (7)
C21	0.0282 (8)	0.0271 (9)	0.0278 (8)	−0.0047 (7)	0.0003 (7)	−0.0002 (7)
C4	0.0286 (9)	0.0318 (10)	0.0455 (11)	−0.0007 (8)	−0.0045 (8)	0.0070 (8)
C16	0.0252 (9)	0.0362 (10)	0.0459 (11)	−0.0027 (8)	−0.0037 (8)	0.0094 (9)
C13	0.0283 (8)	0.0252 (9)	0.0287 (8)	0.0028 (7)	−0.0034 (7)	0.0024 (7)
C25	0.0243 (8)	0.0265 (9)	0.0315 (9)	−0.0021 (7)	0.0024 (7)	0.0013 (7)
C10	0.0285 (8)	0.0250 (9)	0.0248 (8)	−0.0010 (7)	0.0022 (7)	0.0013 (7)
C20	0.0222 (8)	0.0228 (8)	0.0271 (8)	−0.0028 (7)	−0.0003 (6)	−0.0018 (6)
C12	0.0377 (10)	0.0288 (9)	0.0263 (8)	−0.0036 (8)	−0.0031 (7)	0.0019 (7)
C14	0.0382 (10)	0.0365 (10)	0.0269 (9)	−0.0061 (8)	−0.0034 (7)	0.0017 (7)
C7	0.0244 (8)	0.0245 (9)	0.0339 (9)	−0.0008 (7)	0.0042 (7)	0.0018 (7)
C28	0.0519 (14)	0.0285 (11)	0.0372 (11)	−0.0055 (10)	−0.0041 (10)	0.0045 (9)
C23	0.0228 (8)	0.0243 (9)	0.0473 (10)	−0.0008 (7)	0.0011 (7)	−0.0053 (8)
C24	0.0272 (8)	0.0257 (9)	0.0402 (10)	−0.0012 (7)	0.0014 (7)	0.0053 (7)
C8	0.0265 (9)	0.0350 (10)	0.0322 (9)	−0.0002 (8)	0.0066 (7)	0.0009 (7)
C6	0.0278 (9)	0.0306 (10)	0.0420 (10)	0.0023 (7)	0.0069 (8)	−0.0016 (8)
C5	0.0256 (9)	0.0319 (10)	0.0499 (11)	0.0037 (8)	0.0041 (8)	0.0004 (8)
C27	0.0277 (11)	0.0219 (9)	0.0344 (13)	0.0017 (8)	0.0008 (9)	0.0021 (8)
C26	0.0352 (10)	0.0208 (9)	0.0304 (13)	0.0011 (8)	0.0013 (9)	−0.0022 (8)
C26'	0.0277 (11)	0.0219 (9)	0.0344 (13)	0.0017 (8)	0.0008 (9)	0.0021 (8)
C27'	0.0352 (10)	0.0208 (9)	0.0304 (13)	0.0011 (8)	0.0013 (9)	−0.0022 (8)
C15	0.0405 (10)	0.0361 (11)	0.0372 (10)	−0.0099 (9)	−0.0084 (8)	0.0007 (8)
C28'	0.036 (10)	0.052 (13)	0.039 (11)	−0.021 (9)	−0.002 (8)	0.016 (9)

O1—C2	1.374 (2)	C10—H1c10	0.96
O19—C18	1.369 (2)	C12—H1c12	0.96
N11—C10	1.467 (2)	C12—H2c12	0.96
N11—C12	1.465 (2)	C14—C15	1.389 (3)
N11—C26	1.469 (2)	C14—H1c14	0.96
N11—C27'	1.500 (12)	C7—C8	1.501 (2)
N9—C10	1.469 (2)	C7—C6	1.394 (2)
N9—C8	1.473 (2)	C28—C27	1.521 (3)
N9—C27	1.500 (2)	C28—H1c28	0.96
N9—C26'	1.469 (6)	C28—H2c28	0.96
C3—C2	1.380 (2)	C28—H3c28	0.96
C3—C4	1.390 (3)	C23—C24	1.381 (3)
C3—H1c3	0.96	C23—H1c23	0.96
C17—C18	1.389 (2)	C24—H1c24	0.96
C17—C16	1.378 (3)	C8—H1c8	0.96
C17—H1c17	0.96	C8—H2c8	0.96
C22—C21	1.381 (2)	C6—C5	1.381 (3)
C22—C23	1.385 (3)	C6—H1c6	0.96
C22—H1c22	0.96	C5—H1c5	0.96
C2—C7	1.404 (2)	C27—C26	1.525 (3)
C18—C13	1.401 (2)	C27—H1c27	0.96
C21—C20	1.395 (2)	C26—H1c26	0.96
C21—H1c21	0.96	C26—H2c26	0.96
C4—C5	1.380 (3)	C26'—C27'	1.525 (19)
C4—H1c4	0.96	C26'—H1c26'	0.96
C16—C15	1.379 (3)	C26'—H2c26'	0.96
C16—H1c16	0.96	C27'—C28'	1.52 (2)
C13—C12	1.505 (2)	C27'—H1c27'	0.96
C13—C14	1.385 (2)	C15—H1c15	0.96
C25—C20	1.386 (2)	C28'—H1c28'	0.96
C25—C24	1.386 (2)	C28'—H2c28'	0.96
C25—H1c25	0.96	C28'—H3c28'	0.96
C10—C20	1.509 (2)

C10—N11—C12	113.34 (13)	C2—C7—C6	117.97 (15)
C10—N11—C26	102.83 (13)	C8—C7—C6	122.06 (16)
C10—N11—C27'	103.5 (5)	C27—C28—H1c28	109.47
C12—N11—C26	112.84 (13)	C27—C28—H2c28	109.47
C12—N11—C27'	127.6 (5)	C27—C28—H3c28	109.47
C10—N9—C8	111.98 (13)	H1c28—C28—H2c28	109.47
C10—N9—C27	107.30 (13)	H1c28—C28—H3c28	109.47
C10—N9—C26'	103.2 (6)	H2c28—C28—H3c28	109.47
C8—N9—C27	114.89 (14)	C22—C23—C24	119.49 (16)
C8—N9—C26'	97.1 (6)	C22—C23—H1c23	120.25
C2—C3—C4	119.68 (17)	C24—C23—H1c23	120.25
C2—C3—H1c3	120.16	C25—C24—C23	120.18 (16)
C4—C3—H1c3	120.16	C25—C24—H1c24	119.91
C18—C17—C16	120.22 (17)	C23—C24—H1c24	119.91
C18—C17—H1c17	119.89	N9—C8—C7	110.91 (14)
C16—C17—H1c17	119.89	N9—C8—H1c8	109.47
C21—C22—C23	120.50 (16)	N9—C8—H2c8	109.47
C21—C22—H1c22	119.75	C7—C8—H1c8	109.47
C23—C22—H1c22	119.75	C7—C8—H2c8	109.47
O1—C2—C3	119.08 (15)	H1c8—C8—H2c8	108
O1—C2—C7	120.03 (14)	C7—C6—C5	121.38 (17)
C3—C2—C7	120.89 (16)	C7—C6—H1c6	119.31
O19—C18—C17	118.21 (16)	C5—C6—H1c6	119.31
O19—C18—C13	121.29 (15)	C4—C5—C6	119.63 (17)
C17—C18—C13	120.49 (16)	C4—C5—H1c5	120.19
C22—C21—C20	120.31 (15)	C6—C5—H1c5	120.19
C22—C21—H1c21	119.85	N9—C27—C28	111.35 (15)
C20—C21—H1c21	119.85	N9—C27—C26	103.51 (14)
C3—C4—C5	120.43 (17)	N9—C27—H1c27	113.22
C3—C4—H1c4	119.78	C28—C27—C26	112.46 (17)
C5—C4—H1c4	119.78	C28—C27—H1c27	104.42
C17—C16—C15	120.21 (17)	C26—C27—H1c27	112.13
C17—C16—H1c16	119.9	N11—C26—C27	101.74 (14)
C15—C16—H1c16	119.9	N11—C26—H1c26	109.47
C18—C13—C12	120.74 (15)	N11—C26—H2c26	109.47
C18—C13—C14	117.97 (16)	C27—C26—H1c26	109.47
C12—C13—C14	121.27 (15)	C27—C26—H2c26	109.47
C20—C25—C24	120.70 (16)	H1c26—C26—H2c26	116.23
C20—C25—H1c25	119.65	N9—C26'—H1c26'	109.47
C24—C25—H1c25	119.65	N9—C26'—H2c26'	109.47
N11—C10—N9	102.44 (12)	C27'—C26'—H1c26'	109.47
N11—C10—C20	112.26 (13)	C27'—C26'—H2c26'	109.47
N11—C10—H1c10	113.69	H1c26'—C26'—H2c26'	120.28
N9—C10—C20	113.32 (13)	N11—C27'—C26'	107.3 (8)
N9—C10—H1c10	112.64	N11—C27'—C28'	113.3 (11)
C20—C10—H1c10	102.9	N11—C27'—H1c27'	109.44
C21—C20—C25	118.82 (15)	C26'—C27'—C28'	112.5 (12)
C21—C20—C10	120.40 (14)	C26'—C27'—H1c27'	110.35
C25—C20—C10	120.77 (14)	C28'—C27'—H1c27'	103.96
N11—C12—C13	112.27 (13)	C16—C15—C14	119.45 (17)
N11—C12—H1c12	109.47	C16—C15—H1c15	120.27
N11—C12—H2c12	109.47	C14—C15—H1c15	120.27
C13—C12—H1c12	109.47	C27'—C28'—H1c28'	109.47
C13—C12—H2c12	109.47	C27'—C28'—H2c28'	109.47
H1c12—C12—H2c12	106.52	C27'—C28'—H3c28'	109.47
C13—C14—C15	121.65 (17)	H1c28'—C28'—H2c28'	109.47
C13—C14—H1c14	119.18	H1c28'—C28'—H3c28'	109.47
C15—C14—H1c14	119.17	H2c28'—C28'—H3c28'	109.47
C2—C7—C8	119.96 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o1···N9	0.98 (2)	1.88 (2)	2.7569 (18)	147.7 (19)
O19—H1o19···N11	1.00 (2)	1.79 (2)	2.709 (2)	152 (2)
O1—H1o1···C8	0.98 (2)	2.32 (2)	2.844 (2)	112.5 (16)
O19—H1o19···C12	1.00 (2)	2.27 (2)	2.884 (2)	118.6 (16)
O19—H1o19···C28′	1.00 (2)	2.45 (3)	2.877 (18)	105.1 (16)
C26′—H2c26′···C28	0.96	1.63	2.082 (17)	103.83
C28′—H3c28′···O19	0.96	2.35	2.877 (18)	114.12
C26—H1c26···C28′	0.96	1.52	1.973 (15)	102.84

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o1⋯N9	0.98 (2)	1.88 (2)	2.7569 (18)	147.7 (19)
O19—H1o19⋯N11	1.00 (2)	1.79 (2)	2.709 (2)	152 (2)

1 in total

1. 2,2'-[Imidazolidine-1,3-diylbis(methyl-ene)]diphenol.

Authors: Augusto Rivera; Luz Stella Nerio; Jaime Ríos-Motta; Karla Fejfarová; Michal Dušek
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-12-17

1 in total

1. 2,2'-{[2-(2-Hy-droxy-phen-yl)-4-methyl-imidazolidine-1,3-di-yl]bis-(methyl-ene)}diphenol.

Authors: Augusto Rivera; Lorena Cárdenas; Jaime Ríos-Motta; Monika Kučeráková; Michal Dušek
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2013-07-20

1 in total