4,4'-Difluoro-2,2'-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa-hydro-1H-1,3-benzimidazole-1,3-di-yl]bis-(methyl-ene)]}diphenol.

In the crystal structure of the title compound, C(21)H(24)F(2)N(2)O(2), the two N atoms of the imidazolidine moiety are linked to the hy-droxy groups by intra-molecular O-H⋯N hydrogen-bonding inter-actions. The crystal studied was a racemic mixture of RR and SS enatiomers. The cyclo-hexane ring adopts a chair conformation and the imidazolidine group to which it is fused has a twisted envelope conformation.

Related literature

For related structures, see: Rivera et al. (2010a ▶,b ▶, 2011 ▶). For uses of di-Mannich bases, see: Mitra et al. (2006 ▶); Elias et al. (1997 ▶). For related quantum-chemical literature, see: Zierkiewicz & Michalska (2003 ▶); Zierkiewicz et al. (2004 ▶).

Experimental

Crystal data

C21H24F2N2O2

M = 374.4

Triclinic,

a = 5.4605 (1) Å

b = 12.4661 (3) Å

c = 14.3363 (4) Å

α = 108.053 (3)°

β = 91.319 (2)°

γ = 97.437 (2)°

V = 917.98 (4) Å3

Z = 2

Cu Kα radiation

μ = 0.84 mm−1

T = 150 K

0.36 × 0.23 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.516, T max = 1

15846 measured reflections

3248 independent reflections

2819 reflections with I > 3σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.110

S = 1.95

3248 reflections

250 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536811019763/kj2178sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019763/kj2178Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019763/kj2178Isup3.cml

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

C21H24F2N2O2	Z = 2
Mr = 374.4	F(000) = 396
Triclinic, P1	Dx = 1.354 Mg m−3
Hall symbol: -P 1	Melting point: 445 K
a = 5.4605 (1) Å	Cu Kα radiation, λ = 1.5418 Å
b = 12.4661 (3) Å	Cell parameters from 8506 reflections
c = 14.3363 (4) Å	θ = 3.3–67°
α = 108.053 (3)°	µ = 0.84 mm−1
β = 91.319 (2)°	T = 150 K
γ = 97.437 (2)°	Prism, colourless
V = 917.98 (4) Å3	0.36 × 0.23 × 0.09 mm

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	3248 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2819 reflections with I > 3σ(I)
mirror	Rint = 0.024
Detector resolution: 10.3784 pixels mm-1	θmax = 67.1°, θmin = 3.3°
Rotation method data acquisition using ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −14→14
Tmin = 0.516, Tmax = 1	l = −17→17
15846 measured reflections

Refinement on F2	90 constraints
R[F2 > 2σ(F2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
S = 1.95	(Δ/σ)max = 0.006
3248 reflections	Δρmax = 0.25 e Å−3
250 parameters	Δρmin = −0.23 e Å−3
0 restraints

Experimental. CrysAlisPro, Oxford Diffraction (2009), 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
F1	0.8539 (2)	0.55112 (8)	0.62051 (7)	0.0546 (4)
F2	−0.07887 (18)	0.52089 (7)	0.14954 (7)	0.0466 (4)
O1	0.16405 (19)	0.16846 (9)	0.53377 (8)	0.0378 (4)
O2	0.43069 (19)	0.15534 (9)	0.05535 (8)	0.0355 (4)
N1	0.3641 (2)	0.10643 (9)	0.35698 (7)	0.0241 (4)
N2	0.1999 (2)	0.09975 (9)	0.20184 (7)	0.0239 (4)
C1	0.3018 (2)	0.17945 (11)	0.29872 (9)	0.0268 (4)
C2	0.3651 (2)	−0.00695 (11)	0.28492 (9)	0.0240 (4)
C3	0.1458 (2)	−0.01205 (11)	0.21678 (9)	0.0239 (4)
C4	0.1213 (3)	−0.11590 (11)	0.12581 (10)	0.0311 (5)
C5	0.0996 (3)	−0.22171 (12)	0.15961 (11)	0.0358 (5)
C6	0.3115 (3)	−0.21688 (12)	0.23326 (11)	0.0367 (5)
C7	0.3397 (3)	−0.10836 (12)	0.32279 (10)	0.0312 (5)
C8	0.5907 (2)	0.15502 (11)	0.42136 (9)	0.0270 (4)
C9	0.5514 (2)	0.26236 (12)	0.50104 (9)	0.0267 (4)
C10	0.3397 (3)	0.26295 (12)	0.55485 (10)	0.0298 (5)
C11	0.3077 (3)	0.35923 (13)	0.63185 (10)	0.0375 (5)
C12	0.4816 (3)	0.45585 (13)	0.65482 (11)	0.0404 (5)
C13	0.6831 (3)	0.45507 (13)	0.59942 (11)	0.0374 (5)
C14	0.7225 (3)	0.36067 (12)	0.52322 (10)	0.0316 (5)
C15	−0.0045 (2)	0.13892 (11)	0.15950 (9)	0.0262 (4)
C16	0.0880 (2)	0.24381 (11)	0.13227 (9)	0.0244 (4)
C17	0.3020 (3)	0.24648 (12)	0.08027 (9)	0.0279 (4)
C18	0.3842 (3)	0.34067 (13)	0.05171 (10)	0.0343 (5)
C19	0.2565 (3)	0.43379 (13)	0.07452 (11)	0.0363 (5)
C20	0.0492 (3)	0.43006 (12)	0.12624 (10)	0.0327 (5)
C21	−0.0371 (3)	0.33780 (11)	0.15580 (9)	0.0282 (5)
H1a	0.449729	0.225399	0.290412	0.0321*
H1b	0.177063	0.223466	0.329659	0.0321*
H2	0.522627	−0.013546	0.256934	0.0288*
H3	−0.014925	−0.022658	0.241089	0.0287*
H4a	0.266114	−0.112776	0.089503	0.0374*
H4b	−0.02548	−0.118546	0.086507	0.0374*
H5a	0.095707	−0.288587	0.103492	0.0429*
H5b	−0.055536	−0.230187	0.18856	0.0429*
H6a	0.463729	−0.221271	0.200974	0.0441*
H6b	0.284387	−0.282712	0.254988	0.0441*
H7a	0.194886	−0.108455	0.359483	0.0375*
H7b	0.486083	−0.104889	0.362647	0.0375*
H8a	0.723214	0.172323	0.383113	0.0324*
H8b	0.635885	0.100296	0.450802	0.0324*
H11	0.164157	0.358531	0.669188	0.0449*
H12	0.461937	0.522264	0.708518	0.0484*
H14	0.86615	0.362995	0.486129	0.0379*
H15a	−0.127904	0.156161	0.206435	0.0315*
H15b	−0.078638	0.079531	0.101919	0.0315*
H18	0.530423	0.341557	0.015894	0.0411*
H19	0.311842	0.49916	0.054586	0.0435*
H21	−0.182407	0.338481	0.192316	0.0338*
H1o	0.188 (4)	0.1244 (17)	0.4743 (16)	0.0566*
H2o	0.388 (4)	0.1166 (17)	0.0919 (14)	0.0533*

	U11	U22	U33	U12	U13	U23
F1	0.0699 (7)	0.0323 (5)	0.0487 (5)	−0.0063 (5)	−0.0012 (5)	0.0002 (4)
F2	0.0580 (6)	0.0287 (5)	0.0574 (6)	0.0137 (4)	0.0065 (4)	0.0169 (4)
O1	0.0320 (6)	0.0477 (6)	0.0311 (5)	0.0010 (5)	0.0061 (4)	0.0104 (5)
O2	0.0357 (6)	0.0400 (6)	0.0377 (6)	0.0126 (5)	0.0115 (4)	0.0187 (5)
N1	0.0253 (6)	0.0246 (6)	0.0216 (5)	0.0030 (4)	−0.0016 (4)	0.0067 (4)
N2	0.0263 (6)	0.0227 (5)	0.0227 (5)	0.0023 (4)	−0.0016 (4)	0.0079 (4)
C1	0.0307 (7)	0.0248 (6)	0.0243 (6)	0.0026 (5)	−0.0018 (5)	0.0077 (5)
C2	0.0243 (7)	0.0240 (7)	0.0236 (6)	0.0034 (5)	0.0025 (5)	0.0072 (5)
C3	0.0237 (7)	0.0244 (6)	0.0244 (6)	0.0018 (5)	0.0020 (5)	0.0095 (5)
C4	0.0357 (8)	0.0267 (7)	0.0279 (7)	0.0034 (6)	−0.0030 (6)	0.0051 (5)
C5	0.0387 (8)	0.0245 (7)	0.0404 (8)	0.0016 (6)	−0.0034 (6)	0.0065 (6)
C6	0.0394 (8)	0.0248 (7)	0.0470 (9)	0.0048 (6)	−0.0028 (7)	0.0130 (6)
C7	0.0327 (8)	0.0297 (7)	0.0344 (7)	0.0031 (6)	−0.0031 (6)	0.0155 (6)
C8	0.0249 (7)	0.0313 (7)	0.0230 (6)	0.0037 (6)	−0.0011 (5)	0.0063 (5)
C9	0.0278 (7)	0.0305 (7)	0.0212 (6)	0.0063 (5)	−0.0023 (5)	0.0068 (5)
C10	0.0287 (7)	0.0364 (8)	0.0255 (6)	0.0070 (6)	−0.0009 (5)	0.0106 (6)
C11	0.0373 (8)	0.0492 (9)	0.0266 (7)	0.0171 (7)	0.0046 (6)	0.0085 (6)
C12	0.0507 (10)	0.0369 (8)	0.0306 (7)	0.0187 (7)	−0.0013 (7)	0.0018 (6)
C13	0.0448 (9)	0.0291 (7)	0.0339 (7)	0.0023 (6)	−0.0048 (6)	0.0056 (6)
C14	0.0330 (8)	0.0332 (7)	0.0266 (7)	0.0040 (6)	−0.0007 (6)	0.0072 (6)
C15	0.0246 (7)	0.0282 (7)	0.0273 (6)	0.0030 (5)	−0.0013 (5)	0.0114 (5)
C16	0.0258 (7)	0.0272 (7)	0.0197 (6)	0.0011 (5)	−0.0041 (5)	0.0080 (5)
C17	0.0295 (7)	0.0315 (7)	0.0234 (6)	0.0042 (6)	−0.0005 (5)	0.0099 (5)
C18	0.0308 (8)	0.0423 (8)	0.0331 (7)	0.0003 (6)	0.0026 (6)	0.0189 (6)
C19	0.0409 (9)	0.0331 (8)	0.0377 (8)	−0.0027 (6)	−0.0031 (6)	0.0188 (6)
C20	0.0391 (8)	0.0259 (7)	0.0329 (7)	0.0053 (6)	−0.0039 (6)	0.0094 (6)
C21	0.0299 (7)	0.0294 (7)	0.0252 (6)	0.0040 (6)	−0.0005 (5)	0.0088 (5)

F1—C13	1.3668 (17)	C6—H6b	0.96
F2—C20	1.3654 (18)	C7—H7a	0.96
O1—C10	1.3682 (17)	C7—H7b	0.96
O1—H1o	0.88 (2)	C8—C9	1.5100 (17)
O2—C17	1.3706 (18)	C8—H8a	0.96
O2—H2o	0.83 (2)	C8—H8b	0.96
N1—C1	1.477 (2)	C9—C10	1.4041 (19)
N1—C2	1.4704 (15)	C9—C14	1.3873 (19)
N1—C8	1.4686 (16)	C10—C11	1.3897 (18)
N2—C1	1.4805 (14)	C11—C12	1.380 (2)
N2—C3	1.4686 (18)	C11—H11	0.96
N2—C15	1.4652 (19)	C12—C13	1.371 (2)
C1—H1a	0.96	C12—H12	0.96
C1—H1b	0.96	C13—C14	1.3799 (18)
C2—C3	1.5100 (19)	C14—H14	0.96
C2—C7	1.515 (2)	C15—C16	1.507 (2)
C2—H2	0.96	C15—H15a	0.96
C3—C4	1.5151 (16)	C15—H15b	0.96
C3—H3	0.96	C16—C17	1.4032 (19)
C4—C5	1.532 (2)	C16—C21	1.388 (2)
C4—H4a	0.96	C17—C18	1.385 (2)
C4—H4b	0.96	C18—C19	1.388 (2)
C5—C6	1.531 (2)	C18—H18	0.96
C5—H5a	0.96	C19—C20	1.371 (2)
C5—H5b	0.96	C19—H19	0.96
C6—C7	1.5369 (17)	C20—C21	1.377 (2)
C6—H6a	0.96	C21—H21	0.96
C10—O1—H1o	106.9 (13)	H7a—C7—H7b	111.1929
C17—O2—H2o	106.8 (14)	N1—C8—C9	110.50 (11)
C1—N1—C2	105.24 (9)	N1—C8—H8a	109.471
C1—N1—C8	112.56 (10)	N1—C8—H8b	109.471
C2—N1—C8	116.09 (11)	C9—C8—H8a	109.4713
C1—N2—C3	105.27 (10)	C9—C8—H8b	109.4715
C1—N2—C15	113.08 (10)	H8a—C8—H8b	108.4269
C3—N2—C15	116.39 (10)	C8—C9—C10	119.74 (11)
N1—C1—N2	105.37 (10)	C8—C9—C14	121.22 (12)
N1—C1—H1a	109.4709	C10—C9—C14	119.04 (11)
N1—C1—H1b	109.4714	O1—C10—C9	120.76 (11)
N2—C1—H1a	109.4715	O1—C10—C11	118.91 (13)
N2—C1—H1b	109.4707	C9—C10—C11	120.31 (12)
H1a—C1—H1b	113.2798	C10—C11—C12	120.24 (14)
N1—C2—C3	100.30 (10)	C10—C11—H11	119.8818
N1—C2—C7	117.55 (11)	C12—C11—H11	119.8816
N1—C2—H2	111.2215	C11—C12—C13	118.67 (13)
C3—C2—C7	111.58 (10)	C11—C12—H12	120.6647
C3—C2—H2	117.2277	C13—C12—H12	120.6649
C7—C2—H2	99.8589	F1—C13—C12	119.05 (12)
N2—C3—C2	100.48 (9)	F1—C13—C14	118.23 (14)
N2—C3—C4	116.86 (11)	C12—C13—C14	122.72 (14)
N2—C3—H3	111.6886	C9—C14—C13	118.97 (13)
C2—C3—C4	112.03 (11)	C9—C14—H14	120.5126
C2—C3—H3	116.5452	C13—C14—H14	120.5134
C4—C3—H3	100.0584	N2—C15—C16	110.43 (10)
C3—C4—C5	107.76 (12)	N2—C15—H15a	109.4707
C3—C4—H4a	109.4714	N2—C15—H15b	109.4709
C3—C4—H4b	109.4705	C16—C15—H15a	109.4714
C5—C4—H4a	109.4712	C16—C15—H15b	109.4718
C5—C4—H4b	109.4712	H15a—C15—H15b	108.497
H4a—C4—H4b	111.1273	C15—C16—C17	119.77 (12)
C4—C5—C6	112.74 (11)	C15—C16—C21	121.39 (12)
C4—C5—H5a	109.4709	C17—C16—C21	118.82 (13)
C4—C5—H5b	109.4714	O2—C17—C16	120.69 (13)
C6—C5—H5a	109.4711	O2—C17—C18	118.90 (13)
C6—C5—H5b	109.4715	C16—C17—C18	120.40 (14)
H5a—C5—H5b	105.995	C17—C18—C19	120.43 (14)
C5—C6—C7	112.66 (13)	C17—C18—H18	119.7837
C5—C6—H6a	109.471	C19—C18—H18	119.7831
C5—C6—H6b	109.4713	C18—C19—C20	118.30 (15)
C7—C6—H6a	109.4711	C18—C19—H19	120.8492
C7—C6—H6b	109.4714	C20—C19—H19	120.8486
H6a—C6—H6b	106.0781	F2—C20—C19	119.22 (14)
C2—C7—C6	107.69 (12)	F2—C20—C21	118.08 (13)
C2—C7—H7a	109.4718	C19—C20—C21	122.70 (14)
C2—C7—H7b	109.4711	C16—C21—C20	119.33 (13)
C6—C7—H7a	109.4711	C16—C21—H21	120.3339
C6—C7—H7b	109.4711	C20—C21—H21	120.3327
?—?—?—?	?

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.88 (2)	1.92 (2)	2.7105 (15)	147.6 (19)
O1—H1o···C8	0.88 (2)	2.37 (2)	2.8566 (17)	115.3 (15)
O2—H2o···N2	0.83 (2)	1.95 (2)	2.6975 (16)	148 (2)
O2—H2o···C15	0.83 (2)	2.39 (2)	2.8541 (17)	116.0 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.88 (2)	1.92 (2)	2.7105 (15)	147.6 (19)
O2—H2o⋯N2	0.83 (2)	1.95 (2)	2.6975 (16)	148 (2)