4,4'-Dichloro-3,3',5,5'-tetra-methyl-2,2'-[(3aR,7aR/3aS,7aS)-2,3,3a,4,5,6,7,7a-octa-hydro-1H-1,3-benzimidazole-1,3-di-yl)bis-(methyl-ene)]diphenol.

In the title compound, C(25)H(32)Cl(2)N(2)O(2), there are two intra-molecular O-H⋯ N hydrogen-bonding inter-actions between the hy-droxy groups on the aromatic rings and the two N atoms of the heterocyclic group. The cyclo-hexane ring adopts a chair conformation and the imidazolidine unit to which it is fused has a twisted envelope conformation. The asymmetric unit comprises one half-mol-ecule which is completed by a twofold rotation axis. A C-H⋯O inter-action is observed in the crystal structure.

Related literature

For related structures, see: Rivera et al. (2010 ▶); Cox (1995 ▶). For related quantum-chemical literature, see: Zierkiewicz et al. (2000 ▶, 2003 ▶, 2004 ▶).

Experimental

Crystal data

C25H32Cl2N2O2

M = 463.4

Monoclinic,

a = 16.6512 (7) Å

b = 9.6962 (3) Å

c = 14.4423 (6) Å

β = 98.892 (3)°

V = 2303.73 (15) Å3

Z = 4

Cu Kα radiation

μ = 2.73 mm−1

T = 120 K

0.53 × 0.36 × 0.16 mm

Data collection

Agilent Xcalibur diffractometer with Atlas Gemini detector

Absorption correction: analytical (CrysAlis PRO; Agilent, 2010 ▶)’ T min = 0.411, T max = 0.734

32618 measured reflections

2054 independent reflections

1979 reflections with I > 3σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.116

S = 2.54

2054 reflections

144 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.24 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/S1600536811028960/go2020sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028960/go2020Isup2.hkl

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

C25H32Cl2N2O2	F(000) = 984
Mr = 463.4	Dx = 1.336 Mg m−3
Monoclinic, C2/c	Melting point: 498 K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.5418 Å
a = 16.6512 (7) Å	Cell parameters from 23197 reflections
b = 9.6962 (3) Å	θ = 3.1–67°
c = 14.4423 (6) Å	µ = 2.73 mm−1
β = 98.892 (3)°	T = 120 K
V = 2303.73 (15) Å3	Block, colourless
Z = 4	0.53 × 0.36 × 0.16 mm

Agilent Xcalibur diffractometer with Atlas Gemini detector	2054 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1979 reflections with I > 3σ(I)
mirror	Rint = 0.046
Detector resolution: 10.3784 pixels mm-1	θmax = 67.2°, θmin = 5.3°
Rotation method data acquisition using ω scans	h = −19→19
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)'	k = −11→11
Tmin = 0.411, Tmax = 0.734	l = −17→17
32618 measured reflections

Refinement on F2	61 constraints
R[F2 > 2σ(F2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
S = 2.54	(Δ/σ)max = 0.010
2054 reflections	Δρmax = 0.27 e Å−3
144 parameters	Δρmin = −0.24 e Å−3
1 restraint

Experimental. 1H NMR (CDCl3, 400 MHz): δ 1.31 (4H, m), 1.87 (2H, m), 2.08 (2H, m), 2.26 (2H, s, ArCH3), 2.28 (2H, s, ArCH3), 2.36 (2H, m), 2.46 (2H, s, NCH2N), 3.68 (2H, d, 2J = 14.0 Hz, ArCH2N), 4.05 (2H, d, 2J = 14.0 Hz, ArCH2N), 6.57 (2H, s), 11.18 (2H, bs). 13C NMR (CDCl3, 100 MHz): δ 16.7, 21.0, 24.0, 28.9, 53.0, 69.2, 75.8, 116.4, 118.3, 125.4, 133.5, 136.7, 155.9.

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
Cl1	0.76734 (2)	−0.07704 (4)	0.93216 (3)	0.03586 (17)
O1	0.53003 (6)	0.35475 (10)	0.97680 (7)	0.0322 (3)
N1	0.55223 (4)	0.45810 (9)	0.81461 (5)	0.0204 (3)
C1	0.63836 (7)	0.27435 (13)	0.89563 (9)	0.0222 (4)
C2	0.69590 (8)	0.17091 (14)	0.88695 (9)	0.0241 (4)
C3	0.69590 (8)	0.05287 (14)	0.94211 (9)	0.0258 (4)
C4	0.64130 (8)	0.03133 (14)	1.00472 (9)	0.0261 (4)
C5	0.58507 (9)	0.13507 (14)	1.01187 (9)	0.0264 (4)
C6	0.58435 (8)	0.25638 (14)	0.96017 (9)	0.0247 (4)
C7	0.75806 (9)	0.18747 (17)	0.82207 (11)	0.0348 (5)
C8	0.64127 (10)	−0.09641 (15)	1.06364 (10)	0.0326 (4)
C9	0.63587 (8)	0.40679 (14)	0.83881 (9)	0.0237 (4)
C10	0.5	0.36595 (10)	0.75	0.0261 (5)
C11	0.54490 (7)	0.59416 (13)	0.76934 (8)	0.0197 (4)
C12	0.56829 (8)	0.71792 (13)	0.83144 (9)	0.0231 (4)
C13	0.54453 (8)	0.84894 (13)	0.77370 (9)	0.0267 (4)
H1	0.5257 (13)	0.4090 (18)	0.9321 (12)	0.0387*
H5	0.545829	0.122861	1.053384	0.0317*
H7a	0.810554	0.160357	0.854033	0.0522*
H7b	0.743354	0.130427	0.767765	0.0522*
H7c	0.759828	0.28218	0.803107	0.0522*
H8a	0.694459	−0.110125	1.098872	0.0488*
H8b	0.6025	−0.08608	1.105925	0.0488*
H8c	0.626841	−0.174614	1.023772	0.0488*
H9a	0.668777	0.475635	0.874286	0.0284*
H9b	0.658249	0.390095	0.782437	0.0284*
H10	0.533179	0.311486	0.715257	0.0313*
H11	0.582025	0.604471	0.725135	0.0237*
H12a	0.625937	0.717436	0.852045	0.0277*
H12b	0.539438	0.71524	0.884052	0.0277*
H13a	0.57933	0.859112	0.726983	0.032*
H13b	0.554553	0.928472	0.813392	0.032*

	U11	U22	U33	U12	U13	U23
Cl1	0.0336 (3)	0.0301 (3)	0.0424 (3)	0.01390 (13)	0.00143 (18)	−0.00539 (13)
O1	0.0418 (6)	0.0280 (5)	0.0313 (5)	0.0149 (4)	0.0196 (4)	0.0086 (4)
N1	0.0172 (5)	0.0215 (5)	0.0224 (5)	0.0011 (4)	0.0029 (4)	0.0007 (4)
C1	0.0201 (6)	0.0247 (7)	0.0209 (6)	0.0021 (5)	0.0003 (5)	−0.0019 (5)
C2	0.0202 (6)	0.0272 (7)	0.0235 (6)	0.0018 (5)	−0.0006 (5)	−0.0065 (5)
C3	0.0231 (7)	0.0245 (6)	0.0274 (7)	0.0061 (5)	−0.0035 (5)	−0.0075 (5)
C4	0.0307 (7)	0.0235 (7)	0.0217 (6)	0.0032 (5)	−0.0032 (5)	−0.0050 (5)
C5	0.0321 (7)	0.0258 (7)	0.0218 (6)	0.0046 (5)	0.0058 (5)	0.0003 (5)
C6	0.0271 (7)	0.0258 (6)	0.0217 (6)	0.0056 (5)	0.0049 (5)	−0.0019 (5)
C7	0.0263 (7)	0.0401 (8)	0.0393 (8)	0.0072 (6)	0.0096 (6)	−0.0021 (6)
C8	0.0404 (8)	0.0252 (7)	0.0301 (7)	0.0048 (6)	−0.0010 (6)	0.0001 (5)
C9	0.0177 (6)	0.0283 (7)	0.0253 (6)	0.0024 (5)	0.0045 (5)	0.0008 (5)
C10	0.0257 (9)	0.0216 (9)	0.0297 (9)	0	0.0002 (7)	0
C11	0.0196 (7)	0.0223 (6)	0.0180 (6)	−0.0001 (4)	0.0052 (5)	0.0006 (4)
C12	0.0234 (6)	0.0241 (7)	0.0219 (6)	−0.0010 (5)	0.0037 (5)	−0.0006 (5)
C13	0.0324 (8)	0.0225 (6)	0.0254 (6)	−0.0027 (5)	0.0051 (6)	−0.0004 (5)

O1—C6	1.3612 (17)	C7—H7c	0.96
O1—H1	0.827 (17)	C8—H8a	0.96
N1—C9	1.4694 (15)	C8—H8b	0.96
N1—C10	1.4746 (10)	C8—H8c	0.96
N1—C11	1.4691 (15)	C9—H9a	0.96
C1—C2	1.4059 (19)	C9—H9b	0.96
C1—C6	1.4026 (19)	C10—H10	0.96
C1—C9	1.5211 (19)	C10—H10i	0.96
C2—C3	1.3945 (19)	C11—C11i	1.5132 (16)
C2—C7	1.508 (2)	C11—C12	1.5127 (17)
C3—C4	1.394 (2)	C11—H11	0.96
C4—C5	1.389 (2)	C12—C13	1.5376 (18)
C4—C8	1.503 (2)	C12—H12a	0.96
C5—C6	1.3923 (19)	C12—H12b	0.96
C5—H5	0.96	C13—C13i	1.5341 (18)
C7—H7a	0.96	C13—H13a	0.96
C7—H7b	0.96	C13—H13b	0.96
C6—O1—H1	106.8 (14)	H8b—C8—H8c	109.4716
C9—N1—C10	112.95 (8)	N1—C9—C1	111.10 (10)
C9—N1—C11	114.86 (9)	N1—C9—H9a	109.4708
C10—N1—C11	105.20 (7)	N1—C9—H9b	109.4711
C2—C1—C6	119.11 (12)	C1—C9—H9a	109.4716
C2—C1—C9	121.08 (12)	C1—C9—H9b	109.4713
C6—C1—C9	119.77 (12)	H9a—C9—H9b	107.791
C1—C2—C3	118.31 (12)	N1—C10—N1i	105.41 (8)
C1—C2—C7	121.47 (12)	N1—C10—H10	109.4714
C3—C2—C7	120.20 (12)	N1—C10—H10i	109.471
C2—C3—C4	123.46 (13)	N1i—C10—H10	109.471
C3—C4—C5	117.04 (12)	N1i—C10—H10i	109.4714
C3—C4—C8	123.25 (13)	H10—C10—H10i	113.2497
C5—C4—C8	119.71 (13)	N1—C11—C11i	100.00 (9)
C4—C5—C6	121.47 (13)	N1—C11—C12	116.90 (9)
C4—C5—H5	119.2656	N1—C11—H11	111.8254
C6—C5—H5	119.2654	C11i—C11—C12	111.59 (10)
O1—C6—C1	122.83 (12)	C11i—C11—H11	117.1086
O1—C6—C5	116.63 (12)	C12—C11—H11	100.2818
C1—C6—C5	120.53 (13)	C11—C12—C13	108.22 (10)
C2—C7—H7a	109.4708	C11—C12—H12a	109.4707
C2—C7—H7b	109.4713	C11—C12—H12b	109.4717
C2—C7—H7c	109.4707	C13—C12—H12a	109.4709
H7a—C7—H7b	109.4715	C13—C12—H12b	109.4717
H7a—C7—H7c	109.4716	H12a—C12—H12b	110.6913
H7b—C7—H7c	109.4714	C12—C13—C13i	113.08 (11)
C4—C8—H8a	109.4711	C12—C13—H13a	109.4717
C4—C8—H8b	109.4712	C12—C13—H13b	109.4711
C4—C8—H8c	109.471	C13i—C13—H13a	109.4708
H8a—C8—H8b	109.472	C13i—C13—H13b	109.472
H8a—C8—H8c	109.4704	H13a—C13—H13b	105.6049
?—?—?—?	?

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.827 (17)	1.880 (19)	2.6259 (13)	149.4 (19)
C12—H12B···O1ii	0.96	2.56	3.4998 (17)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.827 (17)	1.880 (19)	2.6259 (13)	149.4 (19)
C12—H12B⋯O1i	0.96	2.56	3.4998 (17)	166

Symmetry code: (i) .