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

In the title mol-ecule, C(17)H(20)N(2)O(2), the imidazolidine ring adopts a twist conformation. The mean plane through the five atoms of the imidazolidine ring makes dihedral angles of 70.18 (4) and 74.14 (4)° with the planes of the two aromatic rings. The dihedral angle between the benzene rings is 53.11 (5)°. Both phenol -OH groups form intra-molecular hydrogen bonds to the N atoms, with graph-set motif S(6). In the crystal, pairs of O-H⋯O hydrogen bonds link the mol-ecules into dimers with R(4) (4)(18) ring motifs. The crystal packing is further stabilized by C-H⋯O and weak C-H⋯π inter-actions.

Related literature

For a related structure, see: Rivera et al. (2011 ▶). For the preparation of the title compound, see: Rivera et al. (1993 ▶). For ring conformations, see Cremer & Pople (1975 ▶). For hydrogen-bond graph-set nomenclature, see: Bernstein et al. (1995 ▶). For details of hydrogen bonding in Mannich bases, see: Koll et al. (2006 ▶); Filarowski et al. (1997 ▶).

Experimental

Crystal data

C17H20N2O2

M = 284.4

Monoclinic,

a = 9.6541 (6) Å

b = 9.5198 (11) Å

c = 16.0007 (19) Å

β = 97.321 (7)°

V = 1458.6 (3) Å3

Z = 4

Cu Kα radiation

μ = 0.68 mm−1

T = 120 K

0.56 × 0.46 × 0.35 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.684, T max = 1

16045 measured reflections

2592 independent reflections

2323 reflections with I > 3σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.102

S = 1.84

2592 reflections

197 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811053748/bt5752sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053748/bt5752Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053748/bt5752Isup3.cml

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

C17H20N2O2	F(000) = 608
Mr = 284.4	Dx = 1.295 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2yn	Cell parameters from 9734 reflections
a = 9.6541 (6) Å	θ = 2.8–66.9°
b = 9.5198 (11) Å	µ = 0.68 mm−1
c = 16.0007 (19) Å	T = 120 K
β = 97.321 (7)°	Block, colourless
V = 1458.6 (3) Å3	0.56 × 0.46 × 0.35 mm
Z = 4

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	2592 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2323 reflections with I > 3σ(I)
mirror	Rint = 0.029
Detector resolution: 10.3784 pixels mm-1	θmax = 67.1°, θmin = 5.1°
Rotation method data acquisition using ω scans	h = −10→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→11
Tmin = 0.684, Tmax = 1	l = −18→18
16045 measured reflections

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.032	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
wR(F2) = 0.102	(Δ/σ)max = 0.008
S = 1.84	Δρmax = 0.18 e Å−3
2592 reflections	Δρmin = −0.16 e Å−3
197 parameters	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
2 restraints	Extinction coefficient: 2300 (400)
74 constraints

Experimental. CrysAlisPro (Agilent, 2010) 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	0.88118 (9)	0.55808 (8)	0.54258 (5)	0.0258 (3)
O2	0.64185 (9)	0.24108 (8)	0.20085 (5)	0.0266 (3)
N1	0.82182 (10)	0.29372 (9)	0.50324 (6)	0.0216 (3)
N2	0.75183 (10)	0.27736 (10)	0.36014 (6)	0.0230 (3)
C1	0.73543 (12)	0.41864 (12)	0.62221 (7)	0.0220 (3)
C2	0.78452 (12)	0.54925 (11)	0.59766 (7)	0.0223 (3)
C3	0.73697 (13)	0.67284 (12)	0.63044 (7)	0.0263 (4)
C4	0.64267 (13)	0.66779 (12)	0.68865 (7)	0.0286 (4)
C5	0.59312 (13)	0.53957 (13)	0.71379 (7)	0.0293 (4)
C6	0.63913 (13)	0.41633 (12)	0.67971 (7)	0.0260 (4)
C7	0.79468 (12)	0.28403 (11)	0.59129 (7)	0.0234 (3)
C8	0.69700 (12)	0.29649 (12)	0.44015 (7)	0.0234 (3)
C9	0.89999 (13)	0.17320 (11)	0.47679 (7)	0.0258 (4)
C10	0.86888 (13)	0.17560 (12)	0.38032 (7)	0.0261 (4)
C11	0.80113 (12)	0.41147 (11)	0.32684 (7)	0.0234 (3)
C12	0.84082 (12)	0.39145 (11)	0.23931 (7)	0.0220 (3)
C13	0.75755 (12)	0.30847 (11)	0.18009 (7)	0.0226 (3)
C14	0.79084 (13)	0.29425 (12)	0.09837 (7)	0.0260 (4)
C15	0.90434 (13)	0.36558 (12)	0.07451 (7)	0.0286 (4)
C16	0.98804 (13)	0.44846 (12)	0.13217 (8)	0.0282 (4)
C17	0.95637 (12)	0.45896 (11)	0.21422 (7)	0.0241 (3)
H3	0.769609	0.761889	0.612664	0.0316*
H4	0.611303	0.753394	0.711789	0.0343*
H5	0.527828	0.536104	0.754248	0.0352*
H6	0.603597	0.327787	0.696268	0.0311*
H7a	0.879717	0.260909	0.626476	0.0281*
H7b	0.731088	0.208142	0.597016	0.0281*
H8a	0.637442	0.218852	0.449563	0.0281*
H8b	0.652961	0.386822	0.44087	0.0281*
H9a	0.863665	0.08824	0.497922	0.031*
H9b	0.99806	0.187851	0.493244	0.031*
H10a	0.949631	0.208598	0.356872	0.0313*
H10b	0.83935	0.083954	0.360322	0.0313*
H11a	0.880577	0.444991	0.363629	0.0281*
H11b	0.728563	0.480712	0.325292	0.0281*
H14	0.735192	0.235123	0.058695	0.0312*
H15	0.925546	0.357838	0.017685	0.0343*
H16	1.066759	0.49779	0.115436	0.0338*
H17	1.015526	0.514012	0.254456	0.0289*
H1o	0.8869 (16)	0.4725 (11)	0.5220 (9)	0.0387*
H2o	0.6533 (17)	0.2415 (17)	0.2562 (6)	0.0399*

	U11	U22	U33	U12	U13	U23
O1	0.0292 (5)	0.0224 (4)	0.0271 (4)	−0.0034 (3)	0.0088 (3)	−0.0011 (3)
O2	0.0273 (5)	0.0291 (4)	0.0231 (4)	−0.0045 (3)	0.0026 (3)	−0.0035 (3)
N1	0.0230 (5)	0.0218 (4)	0.0200 (5)	−0.0001 (4)	0.0032 (4)	−0.0009 (3)
N2	0.0263 (5)	0.0222 (5)	0.0209 (5)	−0.0016 (4)	0.0047 (4)	−0.0017 (3)
C1	0.0224 (6)	0.0249 (5)	0.0175 (5)	−0.0003 (4)	−0.0020 (4)	−0.0006 (4)
C2	0.0217 (6)	0.0264 (6)	0.0179 (5)	−0.0008 (4)	−0.0010 (4)	0.0003 (4)
C3	0.0309 (7)	0.0233 (6)	0.0238 (6)	0.0003 (4)	−0.0003 (5)	−0.0004 (4)
C4	0.0315 (7)	0.0281 (6)	0.0257 (6)	0.0049 (5)	0.0012 (5)	−0.0054 (4)
C5	0.0294 (7)	0.0362 (6)	0.0230 (6)	0.0020 (5)	0.0059 (5)	−0.0023 (5)
C6	0.0280 (7)	0.0280 (6)	0.0217 (6)	−0.0028 (5)	0.0030 (5)	0.0010 (4)
C7	0.0279 (6)	0.0222 (5)	0.0203 (6)	−0.0010 (4)	0.0037 (4)	0.0020 (4)
C8	0.0237 (6)	0.0249 (5)	0.0218 (6)	−0.0022 (4)	0.0036 (4)	−0.0013 (4)
C9	0.0292 (7)	0.0223 (5)	0.0266 (6)	0.0023 (4)	0.0060 (5)	−0.0001 (4)
C10	0.0309 (7)	0.0220 (5)	0.0258 (6)	0.0012 (4)	0.0057 (5)	−0.0023 (4)
C11	0.0273 (6)	0.0203 (5)	0.0223 (6)	−0.0023 (4)	0.0019 (5)	−0.0022 (4)
C12	0.0261 (6)	0.0183 (5)	0.0214 (6)	0.0030 (4)	0.0024 (4)	0.0007 (4)
C13	0.0235 (6)	0.0198 (5)	0.0245 (6)	0.0036 (4)	0.0027 (4)	0.0010 (4)
C14	0.0309 (7)	0.0248 (5)	0.0217 (6)	0.0053 (5)	0.0013 (5)	−0.0023 (4)
C15	0.0349 (7)	0.0294 (6)	0.0224 (6)	0.0083 (5)	0.0078 (5)	0.0037 (5)
C16	0.0292 (7)	0.0250 (6)	0.0313 (6)	0.0036 (5)	0.0079 (5)	0.0057 (4)
C17	0.0264 (6)	0.0193 (5)	0.0264 (6)	0.0017 (4)	0.0025 (5)	0.0018 (4)

O1—C2	1.3654 (15)	C7—H7b	0.96
O1—H1o	0.883 (11)	C8—H8a	0.96
O2—C13	1.3653 (14)	C8—H8b	0.96
O2—H2o	0.879 (9)	C9—C10	1.5348 (16)
N1—C7	1.4684 (15)	C9—H9a	0.96
N1—C8	1.4703 (14)	C9—H9b	0.96
N1—C9	1.4650 (15)	C10—H10a	0.96
N2—C8	1.4578 (15)	C10—H10b	0.96
N2—C10	1.4922 (15)	C11—C12	1.5104 (16)
N2—C11	1.4849 (15)	C11—H11a	0.96
C1—C2	1.4044 (16)	C11—H11b	0.96
C1—C6	1.3890 (17)	C12—C13	1.4050 (15)
C1—C7	1.5120 (16)	C12—C17	1.3902 (17)
C2—C3	1.3898 (16)	C13—C14	1.3922 (17)
C3—C4	1.3837 (18)	C14—C15	1.3836 (18)
C3—H3	0.96	C14—H14	0.96
C4—C5	1.3890 (18)	C15—C16	1.3916 (16)
C4—H4	0.96	C15—H15	0.96
C5—C6	1.3902 (17)	C16—C17	1.3890 (18)
C5—H5	0.96	C16—H16	0.96
C6—H6	0.96	C17—H17	0.96
C7—H7a	0.96
C2—O1—H1o	105.3 (10)	H8a—C8—H8b	114.38
C13—O2—H2o	104.0 (10)	N1—C9—C10	103.70 (9)
C7—N1—C8	115.40 (9)	N1—C9—H9a	109.4718
C7—N1—C9	112.92 (8)	N1—C9—H9b	109.4709
C8—N1—C9	102.89 (8)	C10—C9—H9a	109.4712
C8—N2—C10	103.93 (8)	C10—C9—H9b	109.4714
C8—N2—C11	112.12 (9)	H9a—C9—H9b	114.686
C10—N2—C11	111.54 (9)	N2—C10—C9	105.84 (9)
C2—C1—C6	118.51 (10)	N2—C10—H10a	109.4709
C2—C1—C7	120.24 (10)	N2—C10—H10b	109.4713
C6—C1—C7	121.09 (10)	C9—C10—H10a	109.4712
O1—C2—C1	121.18 (10)	C9—C10—H10b	109.4714
O1—C2—C3	118.51 (10)	H10a—C10—H10b	112.8697
C1—C2—C3	120.30 (11)	N2—C11—C12	110.80 (9)
C2—C3—C4	120.12 (11)	N2—C11—H11a	109.4718
C2—C3—H3	119.9399	N2—C11—H11b	109.4711
C4—C3—H3	119.9395	C12—C11—H11a	109.4708
C3—C4—C5	120.39 (11)	C12—C11—H11b	109.4713
C3—C4—H4	119.8038	H11a—C11—H11b	108.1129
C5—C4—H4	119.8053	C11—C12—C13	120.35 (10)
C4—C5—C6	119.27 (12)	C11—C12—C17	121.14 (9)
C4—C5—H5	120.3644	C13—C12—C17	118.45 (10)
C6—C5—H5	120.3649	O2—C13—C12	121.04 (10)
C1—C6—C5	121.38 (11)	O2—C13—C14	118.47 (10)
C1—C6—H6	119.3094	C12—C13—C14	120.49 (11)
C5—C6—H6	119.3085	C13—C14—C15	119.81 (10)
N1—C7—C1	112.45 (9)	C13—C14—H14	120.0949
N1—C7—H7a	109.4718	C15—C14—H14	120.0956
N1—C7—H7b	109.4717	C14—C15—C16	120.58 (11)
C1—C7—H7a	109.4708	C14—C15—H15	119.7101
C1—C7—H7b	109.4707	C16—C15—H15	119.7107
H7a—C7—H7b	106.316	C15—C16—C17	119.23 (11)
N1—C8—N2	104.07 (9)	C15—C16—H16	120.3866
N1—C8—H8a	109.471	C17—C16—H16	120.3878
N1—C8—H8b	109.4708	C12—C17—C16	121.40 (10)
N2—C8—H8a	109.4722	C12—C17—H17	119.2994
N2—C8—H8b	109.4714	C16—C17—H17	119.2985
?—?—?—?	?

Cg3 is the centroid of the C12–C17 benzene rings.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.88 (1)	1.83 (1)	2.6394 (13)	152.(2)
O2—H2o···N2	0.88 (1)	1.84 (1)	2.6557 (13)	154.(2)
O1—H1o···O1i	0.88 (1)	2.60 (2)	3.0232 (12)	111.(1)
C11—H11a···O1i	0.96	2.58	3.4961 (15)	159.
C14—H14···O1ii	0.96	2.50	3.4561 (15)	172.
C6—H6···Cg3iii	0.96	2.97	3.7868 (14)	143
C10—H10b···Cg3ii	0.96	2.83	3.6718 (13)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C12–C17 benzene rings.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.88 (1)	1.83 (1)	2.6394 (13)	152 (2)
O2—H2o⋯N2	0.88 (1)	1.84 (1)	2.6557 (13)	154 (2)
O1—H1o⋯O1i	0.88 (1)	2.60 (2)	3.0232 (12)	111 (1)
C11—H11a⋯O1i	0.96	2.58	3.4961 (15)	159
C14—H14⋯O1ii	0.96	2.50	3.4561 (15)	172
C6—H6⋯Cg3iii	0.96	2.97	3.7868 (14)	143
C10—H10b⋯Cg3ii	0.96	2.83	3.6718 (13)	148

Symmetry codes: (i) ; (ii) ; (iii) .