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

In the title compound, C(17)H(18)F(2)N(2)O(2), the imidazolidine ring system exists in a twist conformation. The mean plane through this ring system forms dihedral angles of 80.8 (8)° and 66.2 (13)°, with the benzene rings. The dihedral angle between the benzene rings is 52.0 (14)°. Two intra-molecular O-H⋯N hydrogen bonds each generate S(6) ring motifs. In the crystal, weak C-H⋯O hydrogen bonds form dimers, which are connected by further C-H⋯O inter-actions.

Related literature

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 ▶). For the involvement of organo halides in hydrogen bonds, see: Rathore et al. (2011 ▶); Steiner (2002 ▶); Chopra & Guru Row (2005 ▶). For the extinction correction used, see: Becker & Coppens (1974 ▶).

Experimental

Crystal data

C17H18F2N2O2

M = 320.3

Monoclinic,

a = 9.5952 (2) Å

b = 9.7018 (2) Å

c = 16.2065 (3) Å

β = 99.4807 (17)°

V = 1488.07 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.94 mm−1

T = 120 K

0.35 × 0.22 × 0.21 mm

Data collection

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.123, T max = 1

35554 measured reflections

2669 independent reflections

2452 reflections with I > 3σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.108

S = 2.21

2669 reflections

215 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.17 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812040329/sj5264sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040329/sj5264Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812040329/sj5264Isup3.cml

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

C17H18F2N2O2	F(000) = 672
Mr = 320.3	Dx = 1.429 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2yabc	Cell parameters from 21321 reflections
a = 9.5952 (2) Å	θ = 4.6–67.0°
b = 9.7018 (2) Å	µ = 0.94 mm−1
c = 16.2065 (3) Å	T = 120 K
β = 99.4807 (17)°	Polygon shape, white
V = 1488.07 (5) Å3	0.35 × 0.22 × 0.21 mm
Z = 4

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer	2669 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2452 reflections with I > 3σ(I)
Mirror monochromator	Rint = 0.025
Detector resolution: 10.3784 pixels mm-1	θmax = 67.1°, θmin = 5.0°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→11
Tmin = 0.123, Tmax = 1	l = −19→19
35554 measured reflections

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.031	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
wR(F2) = 0.108	(Δ/σ)max = 0.009
S = 2.21	Δρmax = 0.19 e Å−3
2669 reflections	Δρmin = −0.17 e Å−3
215 parameters	Extinction correction: B-C type 1 Gaussian isotropic (Becker & Coppens, 1974)
0 restraints	Extinction coefficient: 900 (400)
66 constraints

Experimental. CrysAlisPro, Agilent, 2010Empirical 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
F1	0.58488 (7)	0.98624 (8)	0.11639 (4)	0.0290 (2)
F2	0.02275 (8)	0.97367 (8)	0.76918 (5)	0.0339 (3)
O1	0.37960 (8)	0.95183 (9)	0.53830 (5)	0.0225 (3)
O2	0.14871 (8)	1.28848 (8)	0.20259 (5)	0.0238 (3)
N1	0.25088 (9)	1.23815 (10)	0.36231 (6)	0.0205 (3)
N2	0.32537 (9)	1.21463 (10)	0.50457 (5)	0.0193 (3)
C1	0.30030 (12)	1.22156 (12)	0.59151 (7)	0.0211 (3)
C2	0.25940 (11)	1.21368 (11)	0.18359 (7)	0.0203 (3)
C3	0.45165 (11)	1.05403 (12)	0.21953 (7)	0.0210 (3)
C4	0.39919 (12)	1.14642 (12)	0.07918 (7)	0.0245 (3)
C5	0.33984 (11)	1.12752 (12)	0.24310 (6)	0.0195 (3)
C6	0.28663 (11)	0.96039 (12)	0.59366 (7)	0.0196 (3)
C7	0.24230 (11)	1.08848 (12)	0.62013 (6)	0.0189 (3)
C8	0.15072 (11)	1.09088 (12)	0.67872 (7)	0.0217 (3)
C9	0.40565 (12)	1.33344 (13)	0.48144 (7)	0.0248 (3)
C10	0.14906 (12)	0.84193 (13)	0.68378 (7)	0.0239 (3)
C11	0.29049 (12)	1.22389 (12)	0.10290 (7)	0.0236 (3)
C12	0.23894 (11)	0.83887 (12)	0.62461 (7)	0.0222 (3)
C13	0.36823 (12)	1.33886 (12)	0.38570 (7)	0.0240 (4)
C14	0.19724 (11)	1.21598 (12)	0.44037 (6)	0.0206 (3)
C15	0.47692 (11)	1.06297 (12)	0.13855 (7)	0.0223 (3)
C16	0.10847 (12)	0.96840 (13)	0.70989 (7)	0.0241 (4)
C17	0.30169 (11)	1.10785 (12)	0.32918 (7)	0.0211 (3)
H1c1	0.235801	1.295343	0.597024	0.0253*
H2c1	0.386945	1.24408	0.627648	0.0253*
H1c3	0.510721	0.997491	0.25954	0.0251*
H1c4	0.419502	1.150888	0.023184	0.0294*
H1c8	0.11748	1.177084	0.697131	0.026*
H1c9	0.504952	1.316125	0.497307	0.0297*
H2c9	0.372858	1.415883	0.504826	0.0297*
H1c10	0.116351	0.758191	0.705713	0.0286*
H1c11	0.236448	1.284933	0.063317	0.0283*
H1c12	0.26825	0.751886	0.605019	0.0266*
H1c13	0.335867	1.429715	0.368634	0.0288*
H2c13	0.448556	1.310747	0.361506	0.0288*
H1c14	0.151711	1.127692	0.438843	0.0247*
H2c14	0.138427	1.292231	0.450322	0.0247*
H1c17	0.229709	1.038565	0.326799	0.0253*
H2c17	0.382737	1.074935	0.36675	0.0253*
H2	0.1570 (14)	1.2826 (15)	0.2588 (10)	0.0286*
H1	0.3808 (15)	1.0424 (16)	0.5183 (9)	0.027*

	U11	U22	U33	U12	U13	U23
F1	0.0325 (4)	0.0281 (4)	0.0293 (4)	0.0037 (3)	0.0133 (3)	−0.0034 (3)
F2	0.0408 (4)	0.0331 (5)	0.0338 (4)	0.0006 (3)	0.0235 (3)	0.0031 (3)
O1	0.0263 (4)	0.0211 (5)	0.0221 (4)	0.0031 (3)	0.0096 (3)	−0.0006 (3)
O2	0.0268 (4)	0.0238 (5)	0.0209 (4)	0.0045 (3)	0.0038 (3)	0.0029 (3)
N1	0.0247 (5)	0.0200 (5)	0.0177 (4)	0.0002 (4)	0.0061 (4)	0.0010 (4)
N2	0.0211 (4)	0.0196 (5)	0.0177 (5)	−0.0005 (4)	0.0045 (3)	0.0005 (3)
C1	0.0263 (5)	0.0200 (6)	0.0173 (5)	−0.0004 (4)	0.0045 (4)	−0.0016 (4)
C2	0.0231 (5)	0.0168 (6)	0.0207 (5)	−0.0026 (4)	0.0027 (4)	−0.0006 (4)
C3	0.0240 (5)	0.0170 (6)	0.0214 (6)	−0.0024 (4)	0.0025 (4)	−0.0008 (4)
C4	0.0313 (6)	0.0247 (6)	0.0183 (5)	−0.0058 (5)	0.0067 (4)	−0.0015 (4)
C5	0.0234 (5)	0.0172 (6)	0.0175 (5)	−0.0027 (4)	0.0028 (4)	−0.0008 (4)
C6	0.0191 (5)	0.0235 (6)	0.0155 (5)	0.0010 (4)	0.0011 (4)	−0.0003 (4)
C7	0.0210 (5)	0.0207 (6)	0.0143 (5)	0.0003 (4)	0.0011 (4)	−0.0007 (4)
C8	0.0250 (5)	0.0221 (6)	0.0183 (5)	0.0029 (5)	0.0046 (4)	−0.0010 (4)
C9	0.0281 (6)	0.0228 (6)	0.0242 (6)	−0.0056 (5)	0.0063 (4)	0.0009 (4)
C10	0.0266 (6)	0.0227 (6)	0.0222 (6)	−0.0022 (5)	0.0038 (4)	0.0035 (4)
C11	0.0292 (6)	0.0215 (6)	0.0193 (5)	−0.0027 (5)	0.0015 (4)	0.0028 (4)
C12	0.0261 (6)	0.0199 (6)	0.0201 (5)	0.0020 (4)	0.0022 (4)	−0.0014 (4)
C13	0.0290 (6)	0.0206 (6)	0.0236 (6)	−0.0023 (5)	0.0081 (4)	0.0017 (4)
C14	0.0212 (5)	0.0221 (6)	0.0189 (5)	0.0012 (4)	0.0044 (4)	0.0013 (4)
C15	0.0248 (5)	0.0190 (6)	0.0244 (6)	−0.0028 (4)	0.0075 (4)	−0.0042 (4)
C16	0.0245 (5)	0.0295 (7)	0.0199 (5)	−0.0006 (5)	0.0081 (4)	0.0005 (5)
C17	0.0261 (5)	0.0198 (6)	0.0177 (5)	0.0020 (4)	0.0047 (4)	0.0025 (4)

F1—C15	1.3706 (14)	C4—H1c4	0.96
F2—C16	1.3648 (15)	C5—C17	1.5116 (16)
O1—C6	1.3680 (14)	C6—C7	1.4034 (16)
O1—H1	0.937 (16)	C6—C12	1.3879 (16)
O2—C2	1.3628 (14)	C7—C8	1.3962 (16)
O2—H2	0.903 (16)	C8—C16	1.3780 (17)
N1—C13	1.4919 (14)	C8—H1c8	0.96
N1—C14	1.4581 (15)	C9—C13	1.5348 (15)
N1—C17	1.4867 (15)	C9—H1c9	0.96
N2—C1	1.4694 (14)	C9—H2c9	0.96
N2—C9	1.4689 (15)	C10—C12	1.3916 (17)
N2—C14	1.4741 (13)	C10—C16	1.3750 (17)
C1—C7	1.5089 (16)	C10—H1c10	0.96
C1—H1c1	0.96	C11—H1c11	0.96
C1—H2c1	0.96	C12—H1c12	0.96
C2—C5	1.4070 (14)	C13—H1c13	0.96
C2—C11	1.3918 (16)	C13—H2c13	0.96
C3—C5	1.3928 (16)	C14—H1c14	0.96
C3—C15	1.3761 (16)	C14—H2c14	0.96
C3—H1c3	0.96	C17—H1c17	0.96
C4—C11	1.3902 (17)	C17—H2c17	0.96
C4—C15	1.3789 (15)
C6—O1—H1	102.5 (10)	N2—C9—H2c9	109.47
C2—O2—H2	104.6 (9)	C13—C9—H1c9	109.47
C13—N1—C14	103.64 (8)	C13—C9—H2c9	109.47
C13—N1—C17	111.71 (9)	H1c9—C9—H2c9	114.55
C14—N1—C17	111.82 (9)	C12—C10—C16	118.04 (11)
C1—N2—C9	112.60 (8)	C12—C10—H1c10	120.98
C1—N2—C14	115.28 (9)	C16—C10—H1c10	120.98
C9—N2—C14	102.96 (8)	C2—C11—C4	120.53 (10)
N2—C1—C7	112.49 (9)	C2—C11—H1c11	119.73
N2—C1—H1c1	109.47	C4—C11—H1c11	119.73
N2—C1—H2c1	109.47	C6—C12—C10	120.64 (11)
C7—C1—H1c1	109.47	C6—C12—H1c12	119.68
C7—C1—H2c1	109.47	C10—C12—H1c12	119.68
H1c1—C1—H2c1	106.28	N1—C13—C9	105.99 (9)
O2—C2—C5	121.43 (10)	N1—C13—H1c13	109.47
O2—C2—C11	118.03 (9)	N1—C13—H2c13	109.47
C5—C2—C11	120.53 (10)	C9—C13—H1c13	109.47
C5—C3—C15	119.60 (10)	C9—C13—H2c13	109.47
C5—C3—H1c3	120.2	H1c13—C13—H2c13	112.74
C15—C3—H1c3	120.2	N1—C14—N2	103.95 (8)
C11—C4—C15	117.95 (11)	N1—C14—H1c14	109.47
C11—C4—H1c4	121.03	N1—C14—H2c14	109.47
C15—C4—H1c4	121.03	N2—C14—H1c14	109.47
C2—C5—C3	118.46 (10)	N2—C14—H2c14	109.47
C2—C5—C17	121.24 (10)	H1c14—C14—H2c14	114.48
C3—C5—C17	120.20 (9)	F1—C15—C3	118.37 (9)
O1—C6—C7	121.16 (10)	F1—C15—C4	118.77 (10)
O1—C6—C12	118.35 (10)	C3—C15—C4	122.85 (11)
C7—C6—C12	120.48 (10)	F2—C16—C8	118.27 (11)
C1—C7—C6	121.21 (10)	F2—C16—C10	118.96 (11)
C1—C7—C8	120.01 (10)	C8—C16—C10	122.77 (11)
C6—C7—C8	118.62 (10)	N1—C17—C5	111.70 (9)
C7—C8—C16	119.41 (11)	N1—C17—H1c17	109.47
C7—C8—H1c8	120.29	N1—C17—H2c17	109.47
C16—C8—H1c8	120.29	C5—C17—H1c17	109.47
N2—C9—C13	103.87 (9)	C5—C17—H2c17	109.47
N2—C9—H1c9	109.47	H1c17—C17—H2c17	107.14

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.937 (16)	1.756 (16)	2.6413 (12)	156.2 (14)
O2—H2···N1	0.903 (16)	1.821 (15)	2.6579 (12)	153.2 (13)
C11—H1c11···O1i	0.96	2.44	3.4001 (13)	174.43
C17—H2c17···O1ii	0.96	2.55	3.4837 (13)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.937 (16)	1.756 (16)	2.6413 (12)	156.2 (14)
O2—H2⋯N1	0.903 (16)	1.821 (15)	2.6579 (12)	153.2 (13)
C11—H1c11⋯O1i	0.96	2.44	3.4001 (13)	174.43
C17—H2c17⋯O1ii	0.96	2.55	3.4837 (13)	166

Symmetry codes: (i) ; (ii) .