4,4'-Di-tert-butyl-2,2'-[imidazolidine-1,3-diylbis(methyl-ene)]diphenol.

In the title compound, C25H36N2O2, the two tert-butyl-substituted benzene rings are inclined at an angle of 53.5 (3)° to one another. The imidazolidine ring has an envelope conformation with with one of the C atoms of the ethylene fragment as the flap. The structure displays two intra-molecular O-H⋯N hydrogen bonds that generate S(6) ring motifs. The crystal studied was a non-merohedral twin with a fractional contribution of 0.281(6) for the minor domain.

Related literature

For related structures, see: Rivera et al. (2011 ▶, 2012a ▶,b ▶); Rivera, Nerio, Ríos-Motta, Fejfarová et al. (2012 ▶). For the use of the 2,2′-[imidazolidine-1,3-diylbis(methyl­ene)]diphenol system as a ligand in the synthesis of a variety of coordination compounds, see: Kober et al. (2012 ▶); Xu et al. (2007 ▶); Zhang et al. (2009 ▶). For the original synthesis of the title compound, see: Rivera et al. (1993 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C25H36N2O2

M = 396.56

Monoclinic,

a = 21.0879 (16) Å

b = 6.2110 (4) Å

c = 17.9086 (16) Å

β = 109.168 (6)°

V = 2215.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.24 × 0.22 × 0.19 mm

Data collection

Stoe IPDS II two-circle diffractometer

22835 measured reflections

3909 independent reflections

3131 reflections with I > 2σ(I)

R int = 0.101

Refinement

R[F 2 > 2σ(F 2)] = 0.119

wR(F 2) = 0.324

S = 1.13

3909 reflections

272 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.39 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: XRED-32 (Stoe & Cie, 2001 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813017157/sj5337sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017157/sj5337Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017157/sj5337Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H36N2O2	F(000) = 864
Mr = 396.56	Dx = 1.189 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.0879 (16) Å	Cell parameters from 20905 reflections
b = 6.2110 (4) Å	θ = 2.1–26.0°
c = 17.9086 (16) Å	µ = 0.08 mm−1
β = 109.168 (6)°	T = 173 K
V = 2215.6 (3) Å3	Block, colourless
Z = 4	0.24 × 0.22 × 0.19 mm

Stoe IPDS II two-circle diffractometer	Rint = 0.101
Radiation source: Genix 3D IµS microfocus X-ray source	θmax = 25.0°, θmin = 2.1°
ω scans	h = −25→24
22835 measured reflections	k = −7→7
3909 independent reflections	l = −18→21
3131 reflections with I > 2σ(I)

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.119	w = 1/[σ2(Fo2) + (0.0705P)2 + 10.9502P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.324	(Δ/σ)max < 0.001
S = 1.13	Δρmax = 0.42 e Å−3
3909 reflections	Δρmin = −0.39 e Å−3
272 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.037 (4)

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. Refined as a 2-component twin.

	x	y	z	Uiso*/Ueq
O1	0.4712 (2)	0.0117 (8)	0.5876 (3)	0.0455 (12)
H1	0.500 (5)	0.122 (16)	0.624 (6)	0.09 (3)*
O2	0.6663 (2)	0.9590 (8)	0.7246 (3)	0.0455 (12)
H2	0.635 (4)	0.845 (13)	0.716 (5)	0.06 (2)*
N1	0.5256 (3)	0.3720 (9)	0.6606 (3)	0.0385 (13)
N2	0.6261 (3)	0.5545 (8)	0.7268 (3)	0.0368 (13)
C1	0.5734 (3)	0.4179 (13)	0.7397 (4)	0.0489 (18)
H1A	0.5929	0.2827	0.7669	0.059*
H1B	0.5508	0.4945	0.7724	0.059*
C2	0.5537 (3)	0.4692 (12)	0.6021 (4)	0.0433 (16)
H2A	0.5346	0.6139	0.5854	0.052*
H2B	0.5453	0.3765	0.5549	0.052*
C3	0.6280 (3)	0.4820 (11)	0.6489 (4)	0.0369 (14)
H3A	0.6501	0.3398	0.6525	0.044*
H3B	0.6513	0.5875	0.6256	0.044*
C4	0.4565 (3)	0.4390 (11)	0.6528 (4)	0.0419 (16)
H4A	0.4524	0.5964	0.6437	0.050*
H4B	0.4483	0.4089	0.7031	0.050*
C5	0.6896 (3)	0.5301 (11)	0.7933 (4)	0.0394 (15)
H5A	0.7046	0.3785	0.7960	0.047*
H5B	0.6813	0.5639	0.8434	0.047*
C11	0.4026 (3)	0.3260 (10)	0.5857 (4)	0.0364 (14)
C12	0.4124 (3)	0.1211 (11)	0.5592 (4)	0.0407 (15)
C13	0.3586 (4)	0.0247 (11)	0.5019 (4)	0.0492 (18)
H13	0.3648	−0.1113	0.4810	0.059*
C14	0.2970 (4)	0.1210 (11)	0.4750 (4)	0.0449 (16)
H14	0.2617	0.0508	0.4354	0.054*
C15	0.2846 (3)	0.3197 (10)	0.5040 (4)	0.0399 (15)
C16	0.3396 (3)	0.4209 (11)	0.5576 (4)	0.0421 (16)
H16	0.3339	0.5608	0.5758	0.050*
C17	0.2157 (3)	0.4268 (12)	0.4738 (4)	0.0420 (16)
C18	0.2078 (4)	0.5451 (13)	0.3962 (4)	0.0518 (19)
H18A	0.2141	0.4431	0.3574	0.078*
H18B	0.2415	0.6596	0.4057	0.078*
H18C	0.1628	0.6081	0.3758	0.078*
C19	0.2058 (4)	0.5876 (14)	0.5326 (4)	0.055 (2)
H19A	0.2104	0.5144	0.5825	0.082*
H19B	0.1609	0.6510	0.5114	0.082*
H19C	0.2396	0.7015	0.5417	0.082*
C20	0.1589 (4)	0.2555 (15)	0.4574 (6)	0.066 (2)
H20A	0.1629	0.1777	0.5063	0.099*
H20B	0.1630	0.1537	0.4174	0.099*
H20C	0.1152	0.3272	0.4381	0.099*
C21	0.7443 (3)	0.6742 (10)	0.7855 (4)	0.0363 (14)
C22	0.7299 (3)	0.8793 (10)	0.7516 (4)	0.0403 (15)
C23	0.7822 (3)	1.0074 (11)	0.7463 (4)	0.0434 (16)
H23	0.7731	1.1453	0.7222	0.052*
C24	0.8475 (3)	0.9344 (11)	0.7760 (4)	0.0434 (16)
H24	0.8825	1.0241	0.7715	0.052*
C25	0.8639 (3)	0.7346 (11)	0.8122 (4)	0.0422 (16)
C26	0.8101 (3)	0.6077 (10)	0.8153 (4)	0.0366 (14)
H26	0.8194	0.4693	0.8390	0.044*
C27	0.9369 (3)	0.6602 (12)	0.8458 (5)	0.0506 (18)
C28	0.9627 (4)	0.613 (2)	0.7759 (6)	0.090 (4)
H28A	0.9588	0.7433	0.7438	0.135*
H28B	0.9359	0.4975	0.7432	0.135*
H28C	1.0099	0.5687	0.7964	0.135*
C29	0.9436 (4)	0.4555 (14)	0.8947 (6)	0.069 (2)
H29A	0.9159	0.3417	0.8619	0.103*
H29B	0.9286	0.4836	0.9401	0.103*
H29C	0.9907	0.4094	0.9134	0.103*
C30	0.9809 (4)	0.8335 (14)	0.8977 (6)	0.071 (3)
H30A	0.9768	0.9669	0.8672	0.106*
H30B	1.0278	0.7858	0.9156	0.106*
H30C	0.9665	0.8595	0.9436	0.106*

	U11	U22	U33	U12	U13	U23
O1	0.044 (3)	0.040 (3)	0.055 (3)	0.004 (2)	0.020 (2)	−0.007 (2)
O2	0.039 (3)	0.036 (3)	0.055 (3)	0.004 (2)	0.007 (2)	0.006 (2)
N1	0.034 (3)	0.046 (3)	0.039 (3)	−0.001 (2)	0.017 (2)	0.001 (2)
N2	0.033 (3)	0.039 (3)	0.037 (3)	−0.003 (2)	0.011 (2)	−0.003 (2)
C1	0.039 (4)	0.055 (4)	0.053 (4)	−0.012 (3)	0.014 (3)	0.000 (4)
C2	0.039 (4)	0.047 (4)	0.041 (4)	0.003 (3)	0.010 (3)	0.001 (3)
C3	0.039 (3)	0.038 (3)	0.033 (3)	−0.004 (3)	0.011 (3)	−0.004 (3)
C4	0.036 (3)	0.042 (4)	0.051 (4)	−0.001 (3)	0.020 (3)	−0.008 (3)
C5	0.036 (3)	0.044 (4)	0.036 (3)	0.001 (3)	0.009 (3)	0.002 (3)
C11	0.037 (3)	0.032 (3)	0.041 (4)	−0.004 (3)	0.015 (3)	−0.003 (3)
C12	0.047 (4)	0.039 (4)	0.039 (3)	0.001 (3)	0.017 (3)	0.005 (3)
C13	0.060 (4)	0.032 (3)	0.052 (4)	−0.003 (3)	0.013 (4)	−0.005 (3)
C14	0.051 (4)	0.041 (4)	0.042 (4)	−0.008 (3)	0.014 (3)	−0.006 (3)
C15	0.040 (3)	0.038 (3)	0.042 (4)	−0.004 (3)	0.013 (3)	0.003 (3)
C16	0.038 (3)	0.036 (3)	0.050 (4)	−0.001 (3)	0.012 (3)	−0.001 (3)
C17	0.035 (3)	0.051 (4)	0.041 (4)	−0.001 (3)	0.014 (3)	0.006 (3)
C18	0.048 (4)	0.065 (5)	0.039 (4)	0.001 (4)	0.010 (3)	0.005 (3)
C19	0.048 (4)	0.068 (5)	0.046 (4)	0.013 (4)	0.012 (3)	0.000 (4)
C20	0.040 (4)	0.072 (5)	0.081 (6)	−0.012 (4)	0.011 (4)	0.006 (5)
C21	0.041 (3)	0.035 (3)	0.030 (3)	−0.004 (3)	0.009 (3)	−0.003 (3)
C22	0.042 (4)	0.035 (3)	0.044 (4)	0.000 (3)	0.013 (3)	−0.003 (3)
C23	0.055 (4)	0.036 (3)	0.037 (3)	−0.007 (3)	0.013 (3)	0.005 (3)
C24	0.042 (4)	0.047 (4)	0.043 (4)	−0.013 (3)	0.016 (3)	−0.003 (3)
C25	0.042 (4)	0.042 (4)	0.040 (4)	−0.005 (3)	0.010 (3)	−0.006 (3)
C26	0.036 (3)	0.036 (3)	0.035 (3)	0.001 (3)	0.008 (3)	−0.003 (3)
C27	0.040 (4)	0.055 (4)	0.052 (4)	−0.003 (3)	0.010 (3)	−0.007 (4)
C28	0.049 (5)	0.135 (10)	0.089 (7)	0.009 (6)	0.027 (5)	−0.027 (7)
C29	0.045 (4)	0.056 (5)	0.094 (7)	0.002 (4)	0.007 (4)	0.000 (5)
C30	0.055 (5)	0.055 (5)	0.085 (6)	−0.010 (4)	−0.001 (4)	−0.011 (5)

O1—C12	1.357 (8)	C17—C18	1.533 (10)
O1—H1	1.00 (10)	C17—C20	1.556 (10)
O2—C22	1.360 (8)	C18—H18A	0.9800
O2—H2	0.95 (8)	C18—H18B	0.9800
N1—C1	1.473 (9)	C18—H18C	0.9800
N1—C4	1.478 (8)	C19—H19A	0.9800
N1—C2	1.490 (9)	C19—H19B	0.9800
N2—C1	1.476 (8)	C19—H19C	0.9800
N2—C5	1.479 (8)	C20—H20A	0.9800
N2—C3	1.479 (8)	C20—H20B	0.9800
C1—H1A	0.9900	C20—H20C	0.9800
C1—H1B	0.9900	C21—C26	1.377 (9)
C2—C3	1.517 (9)	C21—C22	1.401 (9)
C2—H2A	0.9900	C22—C23	1.389 (9)
C2—H2B	0.9900	C23—C24	1.378 (10)
C3—H3A	0.9900	C23—H23	0.9500
C3—H3B	0.9900	C24—C25	1.391 (10)
C4—C11	1.526 (9)	C24—H24	0.9500
C4—H4A	0.9900	C25—C26	1.397 (9)
C4—H4B	0.9900	C25—C27	1.529 (9)
C5—C21	1.503 (9)	C26—H26	0.9500
C5—H5A	0.9900	C27—C30	1.522 (10)
C5—H5B	0.9900	C27—C29	1.523 (12)
C11—C16	1.388 (9)	C27—C28	1.549 (12)
C11—C12	1.397 (9)	C28—H28A	0.9800
C12—C13	1.392 (10)	C28—H28B	0.9800
C13—C14	1.365 (10)	C28—H28C	0.9800
C13—H13	0.9500	C29—H29A	0.9800
C14—C15	1.397 (9)	C29—H29B	0.9800
C14—H14	0.9500	C29—H29C	0.9800
C15—C16	1.390 (9)	C30—H30A	0.9800
C15—C17	1.526 (9)	C30—H30B	0.9800
C16—H16	0.9500	C30—H30C	0.9800
C17—C19	1.514 (10)
C12—O1—H1	101 (5)	C18—C17—C20	108.0 (6)
C22—O2—H2	110 (5)	C17—C18—H18A	109.5
C1—N1—C4	112.3 (5)	C17—C18—H18B	109.5
C1—N1—C2	107.0 (5)	H18A—C18—H18B	109.5
C4—N1—C2	115.3 (5)	C17—C18—H18C	109.5
C1—N2—C5	110.1 (5)	H18A—C18—H18C	109.5
C1—N2—C3	103.2 (5)	H18B—C18—H18C	109.5
C5—N2—C3	115.6 (5)	C17—C19—H19A	109.5
N1—C1—N2	105.8 (5)	C17—C19—H19B	109.5
N1—C1—H1A	110.6	H19A—C19—H19B	109.5
N2—C1—H1A	110.6	C17—C19—H19C	109.5
N1—C1—H1B	110.6	H19A—C19—H19C	109.5
N2—C1—H1B	110.6	H19B—C19—H19C	109.5
H1A—C1—H1B	108.7	C17—C20—H20A	109.5
N1—C2—C3	102.2 (5)	C17—C20—H20B	109.5
N1—C2—H2A	111.3	H20A—C20—H20B	109.5
C3—C2—H2A	111.3	C17—C20—H20C	109.5
N1—C2—H2B	111.3	H20A—C20—H20C	109.5
C3—C2—H2B	111.3	H20B—C20—H20C	109.5
H2A—C2—H2B	109.2	C26—C21—C22	119.3 (6)
N2—C3—C2	101.1 (5)	C26—C21—C5	119.5 (6)
N2—C3—H3A	111.5	C22—C21—C5	121.2 (6)
C2—C3—H3A	111.5	O2—C22—C23	118.7 (6)
N2—C3—H3B	111.5	O2—C22—C21	122.2 (6)
C2—C3—H3B	111.5	C23—C22—C21	119.1 (6)
H3A—C3—H3B	109.4	C24—C23—C22	120.0 (6)
N1—C4—C11	113.6 (5)	C24—C23—H23	120.0
N1—C4—H4A	108.8	C22—C23—H23	120.0
C11—C4—H4A	108.8	C23—C24—C25	122.5 (6)
N1—C4—H4B	108.8	C23—C24—H24	118.8
C11—C4—H4B	108.8	C25—C24—H24	118.8
H4A—C4—H4B	107.7	C24—C25—C26	116.2 (6)
N2—C5—C21	112.5 (5)	C24—C25—C27	121.2 (6)
N2—C5—H5A	109.1	C26—C25—C27	122.6 (6)
C21—C5—H5A	109.1	C21—C26—C25	122.9 (6)
N2—C5—H5B	109.1	C21—C26—H26	118.6
C21—C5—H5B	109.1	C25—C26—H26	118.6
H5A—C5—H5B	107.8	C30—C27—C29	108.5 (7)
C16—C11—C12	119.6 (6)	C30—C27—C25	111.1 (6)
C16—C11—C4	117.8 (6)	C29—C27—C25	111.7 (6)
C12—C11—C4	122.1 (6)	C30—C27—C28	108.7 (7)
O1—C12—C13	119.0 (6)	C29—C27—C28	108.4 (8)
O1—C12—C11	123.2 (6)	C25—C27—C28	108.4 (6)
C13—C12—C11	117.8 (6)	C27—C28—H28A	109.5
C14—C13—C12	121.5 (7)	C27—C28—H28B	109.5
C14—C13—H13	119.2	H28A—C28—H28B	109.5
C12—C13—H13	119.2	C27—C28—H28C	109.5
C13—C14—C15	121.9 (7)	H28A—C28—H28C	109.5
C13—C14—H14	119.0	H28B—C28—H28C	109.5
C15—C14—H14	119.0	C27—C29—H29A	109.5
C16—C15—C14	116.1 (6)	C27—C29—H29B	109.5
C16—C15—C17	121.9 (6)	H29A—C29—H29B	109.5
C14—C15—C17	121.8 (6)	C27—C29—H29C	109.5
C11—C16—C15	122.8 (6)	H29A—C29—H29C	109.5
C11—C16—H16	118.6	H29B—C29—H29C	109.5
C15—C16—H16	118.6	C27—C30—H30A	109.5
C19—C17—C15	112.0 (6)	C27—C30—H30B	109.5
C19—C17—C18	108.4 (6)	H30A—C30—H30B	109.5
C15—C17—C18	109.7 (6)	C27—C30—H30C	109.5
C19—C17—C20	108.0 (6)	H30A—C30—H30C	109.5
C15—C17—C20	110.6 (6)	H30B—C30—H30C	109.5
C4—N1—C1—N2	−123.4 (6)	C16—C15—C17—C19	−26.9 (9)
C2—N1—C1—N2	4.0 (7)	C14—C15—C17—C19	157.8 (7)
C5—N2—C1—N1	−154.4 (5)	C16—C15—C17—C18	93.5 (8)
C3—N2—C1—N1	−30.5 (7)	C14—C15—C17—C18	−81.8 (8)
C1—N1—C2—C3	23.1 (7)	C16—C15—C17—C20	−147.5 (7)
C4—N1—C2—C3	148.8 (5)	C14—C15—C17—C20	37.2 (9)
C1—N2—C3—C2	44.4 (6)	N2—C5—C21—C26	−148.4 (6)
C5—N2—C3—C2	164.6 (5)	N2—C5—C21—C22	34.6 (8)
N1—C2—C3—N2	−41.3 (6)	C26—C21—C22—O2	−176.7 (6)
C1—N1—C4—C11	−159.1 (6)	C5—C21—C22—O2	0.3 (10)
C2—N1—C4—C11	77.9 (7)	C26—C21—C22—C23	2.4 (9)
C1—N2—C5—C21	−177.0 (6)	C5—C21—C22—C23	179.4 (6)
C3—N2—C5—C21	66.5 (7)	O2—C22—C23—C24	177.5 (6)
N1—C4—C11—C16	−160.5 (6)	C21—C22—C23—C24	−1.6 (10)
N1—C4—C11—C12	27.4 (9)	C22—C23—C24—C25	−0.4 (11)
C16—C11—C12—O1	−175.5 (6)	C23—C24—C25—C26	1.6 (10)
C4—C11—C12—O1	−3.6 (10)	C23—C24—C25—C27	−178.9 (7)
C16—C11—C12—C13	3.2 (10)	C22—C21—C26—C25	−1.2 (10)
C4—C11—C12—C13	175.2 (6)	C5—C21—C26—C25	−178.2 (6)
O1—C12—C13—C14	175.6 (7)	C24—C25—C26—C21	−0.8 (10)
C11—C12—C13—C14	−3.2 (11)	C27—C25—C26—C21	179.7 (6)
C12—C13—C14—C15	−0.7 (11)	C24—C25—C27—C30	48.9 (10)
C13—C14—C15—C16	4.5 (10)	C26—C25—C27—C30	−131.5 (8)
C13—C14—C15—C17	−180.0 (7)	C24—C25—C27—C29	170.2 (7)
C12—C11—C16—C15	0.7 (10)	C26—C25—C27—C29	−10.3 (10)
C4—C11—C16—C15	−171.6 (6)	C24—C25—C27—C28	−70.4 (9)
C14—C15—C16—C11	−4.4 (10)	C26—C25—C27—C28	109.1 (9)
C17—C15—C16—C11	180.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	1.00 (10)	1.70 (10)	2.655 (7)	157 (8)
O2—H2···N2	0.95 (8)	1.83 (8)	2.656 (7)	144 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	1.00 (10)	1.70 (10)	2.655 (7)	157 (8)
O2—H2⋯N2	0.95 (8)	1.83 (8)	2.656 (7)	144 (7)