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

The imidazolidine ring in the title compound, C(19)H(24)N(2)O(2), adopts a twist conformation and its mean plane (r.m.s. deviation = 0.19 Å) makes dihedral angles of 72.38 (9) and 71.64 (9)° with the two pendant aromatic rings. The dihedral angle between the phenyl rings is 55.94 (8)°. The mol-ecular structure shows the presence of two intra-molecular O-H⋯N hydrogen bonds between the phenolic hydroxyl groups and N atoms with graph-set motif S(6). In the crystal, C-H⋯O hydrogen bonds lead to the formation of chains along the b-axis direction.

Related literature

For the anti-inflammatory and analgesic properties of imidazolidines, see: Sharma & Khan (2001 ▶). For related structures, see: Rivera et al. (2011 ▶, 2012 ▶). For the preparation of the title compound, see: Rivera et al. (1993 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For ring conformations, see Cremer & Pople (1975 ▶). For hydrogen-bond graph-set nomenclature, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H24N2O2

M = 312.4

Monoclinic,

a = 11.5029 (4) Å

b = 9.5001 (3) Å

c = 16.1874 (6) Å

β = 107.078 (3)°

V = 1690.94 (10) Å3

Z = 4

Cu Kα radiation

μ = 0.63 mm−1

T = 120 K

0.25 × 0.22 × 0.13 mm

Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.573, T max = 1

12982 measured reflections

3007 independent reflections

2648 reflections with I > 3σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.104

S = 1.93

3007 reflections

215 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.14 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: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042808/lr2083sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042808/lr2083Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042808/lr2083Isup3.cml

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

C19H24N2O2	F(000) = 672
Mr = 312.4	Dx = 1.227 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2yn	Cell parameters from 8356 reflections
a = 11.5029 (4) Å	θ = 4.0–66.9°
b = 9.5001 (3) Å	µ = 0.63 mm−1
c = 16.1874 (6) Å	T = 120 K
β = 107.078 (3)°	Pyramidal shape, white
V = 1690.94 (10) Å3	0.25 × 0.22 × 0.13 mm
Z = 4

Agilent Xcalibur Atlas Gemini ultra diffractometer	3007 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray source	2648 reflections with I > 3σ(I)
Mirror monochromator	Rint = 0.021
Detector resolution: 10.3784 pixels mm-1	θmax = 67.1°, θmin = 4.2°
ω scans	h = −13→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→11
Tmin = 0.573, Tmax = 1	l = −19→18
12982 measured reflections

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.033	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
wR(F2) = 0.104	(Δ/σ)max = 0.0004
S = 1.93	Δρmax = 0.16 e Å−3
3007 reflections	Δρmin = −0.14 e Å−3
215 parameters	Extinction correction: B-C type 1 Gaussian isotropic (Becker & Coppens, 1974)
0 restraints	Extinction coefficient: 1300 (400)
90 constraints

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq
O1	0.88856 (7)	0.44965 (9)	0.06241 (5)	0.0310 (3)
O2	0.64693 (7)	0.76997 (9)	−0.30769 (6)	0.0290 (3)
N1	0.76722 (9)	0.73615 (10)	−0.13993 (6)	0.0266 (3)
N2	0.84361 (8)	0.71755 (10)	0.00889 (6)	0.0261 (3)
C1	0.74585 (10)	0.70626 (11)	−0.32261 (7)	0.0251 (3)
C2	0.82536 (10)	0.62323 (11)	−0.25869 (7)	0.0243 (3)
C3	0.76676 (10)	0.60644 (12)	0.12013 (7)	0.0247 (3)
C4	0.80273 (10)	0.47037 (12)	0.10465 (7)	0.0267 (4)
C5	0.92398 (10)	0.56062 (11)	−0.27747 (7)	0.0245 (3)
C6	0.86516 (11)	0.66039 (12)	−0.41913 (7)	0.0290 (4)
C7	0.75212 (11)	0.35433 (13)	0.13319 (8)	0.0313 (4)
C8	1.05237 (11)	0.50485 (13)	−0.37565 (8)	0.0305 (4)
C9	0.72950 (10)	0.71770 (12)	−0.06231 (7)	0.0273 (4)
C10	0.94551 (10)	0.57626 (12)	−0.35724 (7)	0.0261 (4)
C11	0.80246 (10)	0.60126 (12)	−0.17246 (7)	0.0256 (4)
C12	0.67858 (10)	0.62103 (12)	0.16280 (7)	0.0262 (4)
C13	0.66608 (11)	0.37235 (13)	0.17686 (8)	0.0315 (4)
C14	0.91127 (11)	0.83498 (14)	−0.01388 (8)	0.0336 (4)
C15	0.87305 (12)	0.83398 (13)	−0.11242 (8)	0.0335 (4)
C16	0.62725 (10)	0.50583 (12)	0.19224 (7)	0.0280 (4)
C17	0.76650 (11)	0.72510 (12)	−0.40199 (8)	0.0283 (4)
C18	0.82742 (10)	0.73307 (12)	0.09490 (7)	0.0272 (4)
C19	0.53567 (12)	0.52729 (15)	0.24135 (9)	0.0374 (4)
H1c5	0.979186	0.504614	−0.233853	0.0294*
H1c6	0.878406	0.67367	−0.474459	0.0348*
H1c7	0.776818	0.261183	0.122626	0.0375*
H1c8	1.072127	0.552979	−0.421921	0.0366*
H2c8	1.121122	0.507333	−0.324784	0.0366*
H3c8	1.031868	0.408791	−0.391977	0.0366*
H1c9	0.689835	0.628276	−0.064525	0.0327*
H2c9	0.680476	0.796361	−0.055893	0.0327*
H1c11	0.738473	0.533616	−0.178617	0.0307*
H2c11	0.874835	0.565476	−0.131679	0.0307*
H1c12	0.652179	0.713903	0.172286	0.0315*
H1c13	0.632626	0.291154	0.196901	0.0378*
H1c14	0.996946	0.816774	0.007957	0.0403*
H2c14	0.886032	0.921709	0.006006	0.0403*
H1c15	0.848056	0.926862	−0.133682	0.0402*
H2c15	0.938576	0.798444	−0.131927	0.0402*
H1c17	0.712548	0.782964	−0.445198	0.034*
H1c18	0.77967	0.81553	0.09603	0.0327*
H2c18	0.905134	0.747643	0.136757	0.0327*
H1c19	0.480459	0.601158	0.21462	0.0449*
H2c19	0.491052	0.441692	0.240675	0.0449*
H3c19	0.577222	0.552689	0.300002	0.0449*
H1	0.6668 (13)	0.7721 (15)	−0.2481 (11)	0.0348*
H2	0.8974 (14)	0.5333 (17)	0.0373 (10)	0.0372*

	U11	U22	U33	U12	U13	U23
O1	0.0325 (5)	0.0315 (5)	0.0289 (4)	0.0074 (3)	0.0088 (3)	−0.0025 (3)
O2	0.0265 (4)	0.0304 (5)	0.0291 (5)	0.0048 (3)	0.0066 (3)	0.0029 (3)
N1	0.0280 (5)	0.0255 (5)	0.0267 (5)	0.0009 (4)	0.0087 (4)	0.0016 (4)
N2	0.0238 (5)	0.0292 (5)	0.0253 (5)	−0.0011 (4)	0.0073 (4)	−0.0005 (4)
C1	0.0243 (6)	0.0208 (5)	0.0284 (6)	−0.0011 (4)	0.0050 (4)	−0.0012 (4)
C2	0.0246 (5)	0.0209 (5)	0.0257 (6)	−0.0031 (4)	0.0048 (4)	0.0003 (4)
C3	0.0251 (5)	0.0261 (6)	0.0203 (5)	0.0005 (4)	0.0026 (4)	−0.0016 (4)
C4	0.0262 (6)	0.0287 (6)	0.0216 (5)	0.0036 (4)	0.0016 (4)	−0.0029 (4)
C5	0.0243 (5)	0.0202 (5)	0.0265 (6)	−0.0012 (4)	0.0034 (4)	0.0007 (4)
C6	0.0345 (6)	0.0273 (6)	0.0248 (6)	−0.0022 (5)	0.0081 (5)	−0.0005 (4)
C7	0.0379 (7)	0.0239 (6)	0.0273 (6)	0.0035 (5)	0.0023 (5)	−0.0017 (5)
C8	0.0311 (6)	0.0295 (6)	0.0311 (6)	−0.0002 (5)	0.0096 (5)	−0.0028 (5)
C9	0.0244 (6)	0.0298 (6)	0.0276 (6)	0.0021 (4)	0.0075 (5)	0.0014 (4)
C10	0.0268 (6)	0.0224 (5)	0.0281 (6)	−0.0032 (4)	0.0065 (4)	−0.0020 (4)
C11	0.0246 (5)	0.0239 (5)	0.0277 (6)	0.0007 (4)	0.0070 (4)	0.0029 (4)
C12	0.0265 (6)	0.0245 (6)	0.0260 (5)	0.0025 (4)	0.0050 (4)	−0.0004 (4)
C13	0.0356 (6)	0.0263 (6)	0.0291 (6)	−0.0046 (5)	0.0041 (5)	0.0024 (5)
C14	0.0305 (6)	0.0366 (7)	0.0344 (6)	−0.0081 (5)	0.0106 (5)	−0.0007 (5)
C15	0.0405 (7)	0.0263 (6)	0.0341 (7)	−0.0053 (5)	0.0114 (5)	0.0014 (5)
C16	0.0254 (6)	0.0292 (6)	0.0260 (6)	−0.0012 (4)	0.0025 (5)	0.0023 (5)
C17	0.0315 (6)	0.0243 (6)	0.0261 (6)	0.0006 (4)	0.0036 (5)	0.0032 (4)
C18	0.0286 (6)	0.0266 (6)	0.0268 (6)	−0.0008 (4)	0.0086 (5)	−0.0036 (4)
C19	0.0332 (7)	0.0377 (7)	0.0435 (7)	0.0000 (5)	0.0147 (6)	0.0070 (5)

O1—C4	1.3701 (16)	C8—C10	1.5084 (18)
O1—H2	0.912 (17)	C8—H1c8	0.96
O2—C1	1.3715 (15)	C8—H2c8	0.96
O2—H1	0.923 (17)	C8—H3c8	0.96
N1—C9	1.4552 (17)	C9—H1c9	0.96
N1—C11	1.4863 (15)	C9—H2c9	0.96
N1—C15	1.4919 (15)	C11—H1c11	0.96
N2—C9	1.4707 (13)	C11—H2c11	0.96
N2—C14	1.4678 (17)	C12—C16	1.3924 (17)
N2—C18	1.4652 (17)	C12—H1c12	0.96
C1—C2	1.4048 (14)	C13—C16	1.3909 (17)
C1—C17	1.3852 (18)	C13—H1c13	0.96
C2—C5	1.3913 (17)	C14—C15	1.5250 (17)
C2—C11	1.5091 (18)	C14—H1c14	0.96
C3—C4	1.4022 (16)	C14—H2c14	0.96
C3—C12	1.3917 (18)	C15—H1c15	0.96
C3—C18	1.5061 (17)	C15—H2c15	0.96
C4—C7	1.3876 (18)	C16—C19	1.508 (2)
C5—C10	1.3923 (18)	C17—H1c17	0.96
C5—H1c5	0.96	C18—H1c18	0.96
C6—C10	1.3974 (15)	C18—H2c18	0.96
C6—C17	1.3884 (18)	C19—H1c19	0.96
C6—H1c6	0.96	C19—H2c19	0.96
C7—C13	1.385 (2)	C19—H3c19	0.96
C7—H1c7	0.96
C4—O1—H2	106.8 (11)	C6—C10—C8	121.43 (11)
C1—O2—H1	103.3 (10)	N1—C11—C2	110.39 (9)
C9—N1—C11	112.56 (9)	N1—C11—H1c11	109.47
C9—N1—C15	103.97 (9)	N1—C11—H2c11	109.47
C11—N1—C15	111.06 (9)	C2—C11—H1c11	109.47
C9—N2—C14	102.68 (9)	C2—C11—H2c11	109.47
C9—N2—C18	114.29 (9)	H1c11—C11—H2c11	108.54
C14—N2—C18	112.76 (9)	C3—C12—C16	122.39 (11)
O2—C1—C2	120.83 (11)	C3—C12—H1c12	118.8
O2—C1—C17	118.92 (9)	C16—C12—H1c12	118.81
C2—C1—C17	120.26 (11)	C7—C13—C16	121.26 (12)
C1—C2—C5	118.38 (11)	C7—C13—H1c13	119.37
C1—C2—C11	120.41 (11)	C16—C13—H1c13	119.37
C5—C2—C11	121.20 (9)	N2—C14—C15	104.28 (9)
C4—C3—C12	118.48 (11)	N2—C14—H1c14	109.47
C4—C3—C18	120.22 (11)	N2—C14—H2c14	109.47
C12—C3—C18	121.22 (10)	C15—C14—H1c14	109.47
O1—C4—C3	121.02 (11)	C15—C14—H2c14	109.47
O1—C4—C7	119.10 (11)	H1c14—C14—H2c14	114.2
C3—C4—C7	119.88 (12)	N1—C15—C14	105.98 (11)
C2—C5—C10	122.38 (9)	N1—C15—H1c15	109.47
C2—C5—H1c5	118.81	N1—C15—H2c15	109.47
C10—C5—H1c5	118.81	C14—C15—H1c15	109.47
C10—C6—C17	121.16 (12)	C14—C15—H2c15	109.47
C10—C6—H1c6	119.42	H1c15—C15—H2c15	112.75
C17—C6—H1c6	119.42	C12—C16—C13	117.69 (12)
C4—C7—C13	120.28 (11)	C12—C16—C19	120.40 (11)
C4—C7—H1c7	119.86	C13—C16—C19	121.88 (12)
C13—C7—H1c7	119.86	C1—C17—C6	120.07 (10)
C10—C8—H1c8	109.47	C1—C17—H1c17	119.97
C10—C8—H2c8	109.47	C6—C17—H1c17	119.97
C10—C8—H3c8	109.47	N2—C18—C3	112.06 (9)
H1c8—C8—H2c8	109.47	N2—C18—H1c18	109.47
H1c8—C8—H3c8	109.47	N2—C18—H2c18	109.47
H2c8—C8—H3c8	109.47	C3—C18—H1c18	109.47
N1—C9—N2	104.65 (9)	C3—C18—H2c18	109.47
N1—C9—H1c9	109.47	H1c18—C18—H2c18	106.76
N1—C9—H2c9	109.47	C16—C19—H1c19	109.47
N2—C9—H1c9	109.47	C16—C19—H2c19	109.47
N2—C9—H2c9	109.47	C16—C19—H3c19	109.47
H1c9—C9—H2c9	113.89	H1c19—C19—H2c19	109.47
C5—C10—C6	117.74 (11)	H1c19—C19—H3c19	109.47
C5—C10—C8	120.83 (9)	H2c19—C19—H3c19	109.47

D—H···A	D—H	H···A	D···A	D—H···A
O1—H2···N2	0.912 (17)	1.869 (16)	2.6893 (13)	148.6 (16)
O2—H1···N1	0.923 (17)	1.825 (15)	2.6807 (12)	153.0 (15)
C17—H1c17···O1i	0.96	2.48	3.4286 (14)	168.38

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H2⋯N2	0.912 (17)	1.869 (16)	2.6893 (13)	148.6 (16)
O2—H1⋯N1	0.923 (17)	1.825 (15)	2.6807 (12)	153.0 (15)
C17—H1c17⋯O1i	0.96	2.48	3.4286 (14)	168.38

Symmetry code: (i) .