4,4'-Dichloro-2,2'-[imidazolidine-1,3-diylbis(methylene)]diphenol.

The imidazolidine ring in the title compound, C(17)H(18)Cl(2)N(2)O(2), adopts a twist conformation. The observed conformation is stabilized by two intra-molecular O-H⋯N hydrogen bonds, with both N atoms acting as hydrogen-bond acceptors. The phenyl substituents are aligned at 70.0 (1) and 76.6 (1)° with respect to the best plane through the five atoms of the imidazolidine ring. Weak inter-molecular C-H⋯O inter-actions stabilize the crystal packing.

Related literature

For the preparation of the title compound, see: Rivera et al. (1993 ▶). For synthetic applications of these di-Mannich bases, see: Rivera & Quevedo (2004 ▶); Rivera et al. (2004 ▶). For a closely related structure, see: Rivera et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For applications of tetra­hydro­salens and heterocalixarenes in medicine and metal-complex catalysis, see: Balsells & Walsh (2000 ▶); Weber et al. (1996 ▶).

Experimental

Crystal data

C17H18Cl2N2O2

M = 353.23

Monoclinic,

a = 10.8640 (2) Å

b = 9.6125 (2) Å

c = 16.7242 (4) Å

β = 106.608 (2)°

V = 1673.65 (6) Å3

Z = 4

Cu Kα radiation

μ = 3.58 mm−1

T = 120 K

0.42 × 0.37 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.669, T max = 0.777

19547 measured reflections

2994 independent reflections

2772 reflections with I > 2σ(I)’

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.101

S = 1.04

2994 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035677/bt5631sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035677/bt5631Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035677/bt5631Isup3.cml

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

C17H18Cl2N2O2	F(000) = 736
Mr = 353.23	Dx = 1.402 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2yn	Cell parameters from 9456 reflections
a = 10.8640 (2) Å	θ = 4.2–67.1°
b = 9.6125 (2) Å	µ = 3.58 mm−1
c = 16.7242 (4) Å	T = 120 K
β = 106.608 (2)°	Prism, colourless
V = 1673.65 (6) Å3	0.42 × 0.37 × 0.25 mm
Z = 4

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	2994 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2772 reflections with I > 2σ(I)'
mirror	Rint = 0.040
Detector resolution: 10.3784 pixels mm-1	θmax = 67.2°, θmin = 4.4°
Rotation method data acquisition using ω scans	h = −12→12
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010)	k = −11→11
Tmin = 0.669, Tmax = 0.777	l = −19→17
19547 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0604P)2 + 0.5161P] where P = (Fo2 + 2Fc2)/3
2994 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.30 e Å−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. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The isotropic temperature parameters of hydrogen atoms were calculated as 1.2*Ueq of the parent atom. The distance between hydrogen and oxygen atom in hydroxyl group was fixed to the distance 0.87 Å.

	x	y	z	Uiso*/Ueq
C1	0.21837 (14)	0.21659 (16)	0.42784 (10)	0.0322 (3)
H1A	0.1749	0.1280	0.4260	0.039*
H1B	0.1608	0.2905	0.4337	0.039*
C2	0.36940 (16)	0.33596 (16)	0.38001 (10)	0.0368 (4)
H2A	0.3437	0.4280	0.3576	0.044*
H2B	0.4409	0.3050	0.3607	0.044*
C3	0.40707 (16)	0.33848 (17)	0.47479 (10)	0.0372 (4)
H3A	0.4991	0.3275	0.4981	0.045*
H3B	0.3809	0.4250	0.4949	0.045*
C4	0.29989 (15)	0.10433 (15)	0.32188 (10)	0.0320 (3)
H4A	0.2325	0.0354	0.3154	0.038*
H4B	0.3766	0.0692	0.3621	0.038*
C5	0.32658 (14)	0.12712 (15)	0.23931 (9)	0.0303 (3)
C6	0.42918 (14)	0.06128 (15)	0.22089 (9)	0.0312 (3)
H6	0.4843	0.0051	0.2607	0.037*
C7	0.44951 (15)	0.07915 (16)	0.14360 (10)	0.0326 (3)
C8	0.37107 (16)	0.16444 (16)	0.08356 (10)	0.0354 (4)
H8	0.3864	0.1763	0.0320	0.043*
C9	0.26963 (16)	0.23171 (16)	0.10149 (10)	0.0351 (4)
H9	0.2168	0.2901	0.0619	0.042*
C10	0.24590 (14)	0.21281 (15)	0.17805 (10)	0.0316 (3)
C11	0.31970 (15)	0.23442 (16)	0.58004 (10)	0.0330 (3)
H11A	0.2605	0.3103	0.5793	0.040*
H11B	0.4013	0.2578	0.6198	0.040*
C12	0.26818 (14)	0.10368 (16)	0.60816 (9)	0.0299 (3)
C13	0.18268 (15)	0.11162 (16)	0.65594 (9)	0.0328 (3)
H13	0.1516	0.1976	0.6667	0.039*
C14	0.14386 (17)	−0.00807 (17)	0.68735 (11)	0.0358 (4)
C15	0.18658 (17)	−0.13748 (17)	0.67129 (10)	0.0387 (4)
H15	0.1597	−0.2173	0.6929	0.046*
C16	0.26995 (16)	−0.14685 (17)	0.62260 (10)	0.0361 (4)
H16	0.2985	−0.2336	0.6109	0.043*
C17	0.31142 (15)	−0.02753 (16)	0.59103 (10)	0.0311 (3)
N1	0.25961 (12)	0.23659 (13)	0.35315 (8)	0.0322 (3)
N2	0.33788 (12)	0.21975 (13)	0.49679 (8)	0.0300 (3)
O1	0.14312 (10)	0.27831 (11)	0.19253 (7)	0.0364 (3)
H1O1	0.1592	0.2802	0.2528	0.044*
O2	0.39647 (10)	−0.04067 (12)	0.54511 (7)	0.0348 (3)
H1O2	0.4004	0.0494	0.5208	0.042*
Cl1	0.57874 (4)	−0.00643 (4)	0.12223 (3)	0.03906 (15)
Cl2	0.04238 (5)	0.00586 (5)	0.75129 (3)	0.04919 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0287 (7)	0.0310 (8)	0.0365 (8)	0.0010 (6)	0.0086 (6)	0.0027 (6)
C2	0.0402 (9)	0.0281 (8)	0.0418 (9)	−0.0043 (6)	0.0116 (7)	0.0039 (6)
C3	0.0384 (8)	0.0313 (8)	0.0417 (9)	−0.0080 (6)	0.0111 (7)	−0.0005 (6)
C4	0.0335 (8)	0.0265 (7)	0.0346 (8)	0.0011 (6)	0.0073 (6)	0.0047 (6)
C5	0.0323 (7)	0.0237 (7)	0.0317 (8)	−0.0034 (6)	0.0039 (6)	0.0025 (6)
C6	0.0316 (7)	0.0245 (7)	0.0332 (8)	−0.0015 (6)	0.0025 (6)	0.0014 (6)
C7	0.0343 (8)	0.0257 (7)	0.0368 (8)	−0.0026 (6)	0.0083 (6)	−0.0026 (6)
C8	0.0437 (9)	0.0294 (8)	0.0321 (8)	−0.0033 (6)	0.0090 (7)	0.0008 (6)
C9	0.0404 (9)	0.0273 (8)	0.0328 (8)	0.0009 (6)	0.0025 (7)	0.0046 (6)
C10	0.0312 (7)	0.0240 (7)	0.0360 (8)	−0.0020 (6)	0.0043 (6)	0.0008 (6)
C11	0.0367 (8)	0.0263 (7)	0.0355 (8)	−0.0008 (6)	0.0094 (7)	−0.0034 (6)
C12	0.0289 (7)	0.0286 (8)	0.0290 (7)	0.0006 (6)	0.0029 (6)	−0.0009 (6)
C13	0.0337 (8)	0.0322 (8)	0.0301 (8)	0.0025 (6)	0.0052 (6)	0.0002 (6)
C14	0.0339 (8)	0.0402 (9)	0.0307 (8)	−0.0035 (6)	0.0053 (7)	0.0011 (6)
C15	0.0442 (9)	0.0320 (8)	0.0350 (8)	−0.0078 (7)	0.0036 (7)	0.0040 (7)
C16	0.0415 (9)	0.0266 (7)	0.0351 (8)	0.0008 (6)	0.0026 (7)	−0.0015 (6)
C17	0.0299 (7)	0.0296 (7)	0.0291 (8)	0.0007 (6)	0.0008 (6)	−0.0018 (6)
N1	0.0327 (6)	0.0264 (6)	0.0368 (7)	0.0001 (5)	0.0089 (6)	0.0035 (5)
N2	0.0286 (6)	0.0279 (6)	0.0330 (7)	−0.0015 (5)	0.0081 (5)	−0.0007 (5)
O1	0.0341 (6)	0.0341 (6)	0.0385 (6)	0.0057 (4)	0.0063 (5)	0.0060 (5)
O2	0.0353 (6)	0.0299 (5)	0.0395 (6)	0.0045 (4)	0.0109 (5)	−0.0021 (5)
Cl1	0.0404 (3)	0.0345 (2)	0.0437 (3)	0.00186 (14)	0.01431 (19)	−0.00169 (15)
Cl2	0.0477 (3)	0.0585 (3)	0.0470 (3)	−0.00269 (18)	0.0226 (2)	0.00619 (18)

C1—N1	1.455 (2)	C8—H8	0.9300
C1—N2	1.470 (2)	C9—C10	1.388 (2)
C1—H1A	0.9700	C9—H9	0.9300
C1—H1B	0.9700	C10—O1	1.3625 (19)
C2—N1	1.494 (2)	C11—N2	1.468 (2)
C2—C3	1.520 (2)	C11—C12	1.505 (2)
C2—H2A	0.9700	C11—H11A	0.9700
C2—H2B	0.9700	C11—H11B	0.9700
C3—N2	1.470 (2)	C12—C13	1.390 (2)
C3—H3A	0.9700	C12—C17	1.404 (2)
C3—H3B	0.9700	C13—C14	1.380 (2)
C4—N1	1.4873 (19)	C13—H13	0.9300
C4—C5	1.506 (2)	C14—C15	1.381 (2)
C4—H4A	0.9700	C14—Cl2	1.7466 (18)
C4—H4B	0.9700	C15—C16	1.383 (3)
C5—C6	1.391 (2)	C15—H15	0.9300
C5—C10	1.408 (2)	C16—C17	1.390 (2)
C6—C7	1.383 (2)	C16—H16	0.9300
C6—H6	0.9300	C17—O2	1.366 (2)
C7—C8	1.385 (2)	O1—H1O1	0.9725
C7—Cl1	1.7500 (16)	O2—H1O2	0.9623
C8—C9	1.383 (2)
N1—C1—N2	104.54 (12)	C8—C9—H9	119.7
N1—C1—H1A	110.8	C10—C9—H9	119.7
N2—C1—H1A	110.8	O1—C10—C9	118.76 (14)
N1—C1—H1B	110.8	O1—C10—C5	120.82 (14)
N2—C1—H1B	110.8	C9—C10—C5	120.42 (14)
H1A—C1—H1B	108.9	N2—C11—C12	112.28 (12)
N1—C2—C3	106.13 (12)	N2—C11—H11A	109.1
N1—C2—H2A	110.5	C12—C11—H11A	109.1
C3—C2—H2A	110.5	N2—C11—H11B	109.1
N1—C2—H2B	110.5	C12—C11—H11B	109.1
C3—C2—H2B	110.5	H11A—C11—H11B	107.9
H2A—C2—H2B	108.7	C13—C12—C17	118.97 (14)
N2—C3—C2	104.13 (12)	C13—C12—C11	120.21 (14)
N2—C3—H3A	110.9	C17—C12—C11	120.70 (14)
C2—C3—H3A	110.9	C14—C13—C12	120.02 (15)
N2—C3—H3B	110.9	C14—C13—H13	120.0
C2—C3—H3B	110.9	C12—C13—H13	120.0
H3A—C3—H3B	108.9	C13—C14—C15	121.39 (16)
N1—C4—C5	110.56 (12)	C13—C14—Cl2	118.96 (13)
N1—C4—H4A	109.5	C15—C14—Cl2	119.62 (13)
C5—C4—H4A	109.5	C14—C15—C16	119.09 (15)
N1—C4—H4B	109.5	C14—C15—H15	120.5
C5—C4—H4B	109.5	C16—C15—H15	120.5
H4A—C4—H4B	108.1	C15—C16—C17	120.51 (15)
C6—C5—C10	118.47 (14)	C15—C16—H16	119.7
C6—C5—C4	120.89 (13)	C17—C16—H16	119.7
C10—C5—C4	120.61 (14)	O2—C17—C16	118.82 (14)
C7—C6—C5	120.18 (14)	O2—C17—C12	121.17 (14)
C7—C6—H6	119.9	C16—C17—C12	120.00 (15)
C5—C6—H6	119.9	C1—N1—C4	112.49 (12)
C6—C7—C8	121.45 (14)	C1—N1—C2	103.98 (12)
C6—C7—Cl1	118.97 (12)	C4—N1—C2	111.25 (12)
C8—C7—Cl1	119.57 (12)	C11—N2—C1	114.70 (12)
C9—C8—C7	118.89 (15)	C11—N2—C3	112.33 (12)
C9—C8—H8	120.6	C1—N2—C3	102.70 (12)
C7—C8—H8	120.6	C10—O1—H1O1	106.2
C8—C9—C10	120.56 (14)	C17—O2—H1O2	105.8
?—?—?—?	?

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.97	1.77	2.6524 (17)	149
O2—H1O2···N2	0.96	1.77	2.6515 (17)	150
C4—H4B···O2i	0.97	2.52	3.466 (2)	163
C9—H9···O2ii	0.93	2.47	3.395 (2)	172
C11—H11B···O1iii	0.97	2.58	3.482 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1	0.97	1.77	2.6524 (17)	149
O2—H1O2⋯N2	0.96	1.77	2.6515 (17)	150
C4—H4B⋯O2i	0.97	2.52	3.466 (2)	163
C9—H9⋯O2ii	0.93	2.47	3.395 (2)	172
C11—H11B⋯O1iii	0.97	2.58	3.482 (2)	154

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