6,6'-Dimethyl-2,2'-[imidazolidine-1,3-diyl-bis(methyl-ene)]diphenol.

In the title compound, C19H24N2O2, a di-Mannich base derived from 2-methyl-phenol and 1,3,6,8-tetra-aza-tri-cyclo-[4.4.1.1(3,8)]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-hy-droxy-3-methyl-benzyl groups are located in trans positions with respect to the imidazolidine fragment. The structure displays two intra-molecular O-H⋯N hydrogen bonds, which each form an S(6) ring motif. In the crystal, the mol-ecules are linked by weak C-H⋯O inter-actions with a bifurcated acceptor, forming a three-dimensional network.

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

C19H24N2O2

M = 312.40

Monoclinic,

a = 12.6271 (11) Å

b = 13.5780 (9) Å

c = 10.1997 (9) Å

β = 107.940 (7)°

V = 1663.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.33 × 0.13 × 0.12 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001 ▶) T min = 0.974, T max = 0.990

16285 measured reflections

3207 independent reflections

2803 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.114

S = 1.07

3207 reflections

219 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: 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.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814002128/fb2295sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002128/fb2295Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002128/fb2295Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) .