4,4'-Diiodo-2,2'-[(3aR,7aR)-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)I(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 cyclo-hexane ring adopts a chair conformation and the heterocyclic ring to which it is fused has a twisted envelope conformation.

Related literature

For related structures, see: Rivera et al. (2010 ▶, 2011a ▶,b ▶); Merz (2006 ▶).

Experimental

Crystal data

C21H24I2N2O2

M = 590.2

Monoclinic,

a = 24.5822 (12) Å

b = 6.1121 (3) Å

c = 16.5557 (10) Å

β = 121.119 (6)°

V = 2129.5 (2) Å3

Z = 4

Cu Kα radiation

μ = 23.34 mm−1

T = 120 K

0.26 × 0.12 × 0.05 mm

Data collection

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

Absorption correction: analytical (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.074, T max = 0.424

11449 measured reflections

3650 independent reflections

3397 reflections with I > 3σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.106

S = 1.30

3650 reflections

250 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.85 e Å−3

Δρmin = −0.87 e Å−3

Absolute structure: Flack (1983 ▶), 1566 Friedel pairs

Flack parameter: 0.079 (13)

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/S1600536811030054/nc2238sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030054/nc2238Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030054/nc2238Isup3.cml

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

C21H24I2N2O2	F(000) = 1144
Mr = 590.2	Dx = 1.840 Mg m−3
Monoclinic, C2	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: C 2y	Cell parameters from 5885 reflections
a = 24.5822 (12) Å	θ = 3.1–67.1°
b = 6.1121 (3) Å	µ = 23.34 mm−1
c = 16.5557 (10) Å	T = 120 K
β = 121.119 (6)°	Prism, colourless
V = 2129.5 (2) Å3	0.26 × 0.12 × 0.05 mm
Z = 4

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	3650 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	3397 reflections with I > 3σ(I)
mirror	Rint = 0.062
Detector resolution: 10.3784 pixels mm-1	θmax = 67.2°, θmin = 3.1°
Rotation method data acquisition using ω scans	h = −29→29
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)	k = −7→7
Tmin = 0.074, Tmax = 0.424	l = −19→19
11449 measured reflections

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.040	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
wR(F2) = 0.106	(Δ/σ)max = 0.038
S = 1.30	Δρmax = 0.85 e Å−3
3650 reflections	Δρmin = −0.87 e Å−3
250 parameters	Absolute structure: Flack (1983), 1566 Friedel pairs
2 restraints	Flack parameter: 0.079 (13)
91 constraints

Experimental. CrysAlis Pro (Agilent, 2010), Analytical numeric absorption correction using a multifaceted crystal model.

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.The absolute structure was determined on the basis of 1566 Friedel pairs (Flack, 1983),

	x	y	z	Uiso*/Ueq
I1	0.40926 (2)	0.38885	0.03435 (3)	0.0457 (2)
I2	0.54564 (3)	0.34180 (15)	0.67075 (4)	0.0621 (3)
O1	0.2558 (2)	0.8312 (10)	0.1940 (3)	0.040 (2)
O2	0.2940 (3)	−0.1604 (11)	0.4035 (4)	0.054 (3)
N1	0.2165 (3)	0.4306 (11)	0.2051 (4)	0.034 (2)
N2	0.2436 (3)	0.2401 (11)	0.3459 (4)	0.035 (3)
C1	0.2707 (3)	0.3359 (13)	0.2912 (4)	0.034 (3)
C2	0.1598 (3)	0.3332 (14)	0.1992 (4)	0.036 (3)
C3	0.1790 (3)	0.3314 (15)	0.3014 (5)	0.038 (3)
C4	0.1317 (4)	0.2045 (16)	0.3154 (6)	0.045 (4)
C5	0.0666 (4)	0.314 (2)	0.2559 (6)	0.061 (5)
C6	0.0474 (3)	0.335 (2)	0.1518 (5)	0.051 (4)
C7	0.0975 (4)	0.4517 (15)	0.1400 (5)	0.042 (3)
C8	0.2198 (3)	0.3905 (16)	0.1187 (4)	0.031 (3)
C9	0.2733 (3)	0.5131 (13)	0.1224 (5)	0.034 (3)
C10	0.2890 (4)	0.7266 (14)	0.1603 (5)	0.035 (3)
C11	0.3386 (3)	0.8414 (15)	0.1623 (4)	0.037 (3)
C12	0.3732 (4)	0.7461 (14)	0.1254 (5)	0.042 (3)
C13	0.3568 (4)	0.5396 (14)	0.0869 (5)	0.037 (3)
C14	0.3084 (3)	0.4225 (12)	0.0860 (4)	0.031 (3)
C15	0.2835 (4)	0.2855 (14)	0.4477 (5)	0.038 (3)
C16	0.3459 (4)	0.1688 (14)	0.4877 (5)	0.038 (3)
C17	0.3489 (4)	−0.0472 (14)	0.4615 (5)	0.042 (4)
C18	0.4071 (4)	−0.1506 (18)	0.4971 (6)	0.052 (4)
C19	0.4628 (5)	−0.0464 (14)	0.5584 (6)	0.046 (4)
C20	0.4608 (4)	0.1693 (16)	0.5825 (6)	0.047 (4)
C21	0.4035 (4)	0.2758 (15)	0.5479 (5)	0.041 (3)
H1a	0.30018	0.449807	0.327486	0.041*
H1b	0.289698	0.222021	0.273989	0.041*
H2	0.150156	0.194368	0.167635	0.0427*
H3	0.179095	0.470059	0.328724	0.046*
H4a	0.144224	0.208887	0.380735	0.0534*
H4b	0.129369	0.056584	0.294365	0.0534*
H5a	0.067702	0.456816	0.281037	0.0736*
H5b	0.035132	0.23068	0.260104	0.0736*
H6a	0.039828	0.192423	0.123906	0.0611*
H6b	0.007888	0.412918	0.117567	0.0611*
H7a	0.085623	0.447024	0.074901	0.0506*
H7b	0.101731	0.600035	0.161522	0.0506*
H8a	0.22518	0.236821	0.113022	0.0373*
H8b	0.180562	0.434385	0.06391	0.0373*
H11	0.349133	0.985749	0.188885	0.0443*
H12	0.40771	0.823632	0.127037	0.05*
H14	0.298725	0.277391	0.060112	0.0371*
H15a	0.290776	0.440117	0.457354	0.0451*
H15b	0.26204	0.236075	0.479059	0.0451*
H18	0.408329	−0.298327	0.478383	0.0625*
H19	0.502706	−0.121714	0.584329	0.0552*
H21	0.402993	0.425237	0.565416	0.0489*
H1O	0.240 (4)	0.728 (11)	0.209 (7)	0.0482*
H2O	0.270 (4)	−0.059 (13)	0.370 (7)	0.0643*

	U11	U22	U33	U12	U13	U23
I1	0.0504 (2)	0.0491 (3)	0.0454 (2)	−0.0022 (2)	0.0304 (2)	−0.0027 (2)
I2	0.0572 (3)	0.0623 (5)	0.0429 (3)	0.0124 (3)	0.0089 (2)	−0.0038 (3)
O1	0.054 (3)	0.030 (3)	0.042 (2)	−0.003 (2)	0.028 (2)	−0.001 (2)
O2	0.090 (4)	0.025 (4)	0.047 (3)	−0.007 (3)	0.036 (3)	−0.004 (3)
N1	0.045 (3)	0.031 (4)	0.029 (3)	−0.005 (2)	0.021 (2)	−0.004 (2)
N2	0.048 (3)	0.032 (4)	0.026 (3)	−0.007 (3)	0.020 (3)	−0.003 (2)
C1	0.045 (3)	0.030 (4)	0.031 (3)	−0.005 (3)	0.022 (3)	0.000 (3)
C2	0.045 (3)	0.035 (5)	0.033 (3)	−0.008 (3)	0.025 (3)	−0.003 (3)
C3	0.050 (4)	0.033 (5)	0.034 (3)	−0.005 (3)	0.024 (3)	−0.001 (3)
C4	0.058 (4)	0.046 (5)	0.039 (4)	−0.011 (4)	0.031 (4)	0.000 (4)
C5	0.057 (5)	0.088 (9)	0.047 (4)	−0.008 (5)	0.033 (4)	−0.001 (5)
C6	0.042 (4)	0.070 (7)	0.044 (4)	−0.009 (4)	0.025 (3)	−0.006 (5)
C7	0.051 (4)	0.043 (5)	0.034 (4)	−0.004 (3)	0.022 (3)	0.000 (3)
C8	0.039 (3)	0.023 (4)	0.026 (3)	−0.001 (3)	0.013 (2)	0.006 (3)
C9	0.043 (4)	0.034 (5)	0.022 (3)	0.000 (3)	0.015 (3)	0.007 (3)
C10	0.041 (4)	0.034 (5)	0.028 (3)	−0.004 (3)	0.016 (3)	−0.003 (3)
C11	0.047 (3)	0.029 (5)	0.029 (3)	−0.005 (3)	0.016 (3)	−0.003 (3)
C12	0.046 (4)	0.040 (5)	0.034 (4)	−0.006 (3)	0.017 (3)	0.004 (3)
C13	0.043 (4)	0.040 (5)	0.033 (4)	−0.001 (3)	0.022 (3)	−0.001 (3)
C14	0.046 (3)	0.020 (4)	0.023 (3)	−0.004 (3)	0.015 (3)	0.000 (3)
C15	0.059 (4)	0.031 (5)	0.029 (3)	0.005 (3)	0.028 (3)	0.001 (3)
C16	0.062 (5)	0.025 (4)	0.028 (4)	0.003 (3)	0.024 (4)	0.002 (3)
C17	0.075 (5)	0.025 (5)	0.033 (4)	−0.004 (4)	0.034 (4)	−0.003 (3)
C18	0.092 (6)	0.028 (6)	0.048 (4)	0.008 (5)	0.044 (4)	−0.003 (4)
C19	0.078 (6)	0.031 (5)	0.041 (4)	0.014 (4)	0.039 (4)	0.009 (3)
C20	0.060 (5)	0.043 (5)	0.034 (4)	0.013 (4)	0.023 (4)	0.009 (4)
C21	0.063 (5)	0.032 (5)	0.027 (3)	0.006 (3)	0.023 (3)	0.003 (3)

I1—C13	2.105 (10)	C6—H6b	0.96
I2—C20	2.108 (8)	C7—H7a	0.96
O1—C10	1.363 (12)	C7—H7b	0.96
O1—H1O	0.84 (10)	C8—C9	1.488 (12)
O2—C17	1.372 (10)	C8—H8a	0.96
O2—H2O	0.84 (8)	C8—H8b	0.96
N1—C1	1.476 (7)	C9—C10	1.412 (11)
N1—C2	1.471 (11)	C9—C14	1.396 (13)
N1—C8	1.494 (11)	C10—C11	1.392 (13)
N2—C1	1.494 (12)	C11—C12	1.405 (14)
N2—C3	1.473 (10)	C11—H11	0.96
N2—C15	1.472 (9)	C12—C13	1.377 (12)
C1—H1a	0.96	C12—H12	0.96
C1—H1b	0.96	C13—C14	1.383 (12)
C2—C3	1.503 (11)	C14—H14	0.96
C2—C7	1.510 (10)	C15—C16	1.501 (12)
C2—H2	0.96	C15—H15a	0.96
C3—C4	1.511 (14)	C15—H15b	0.96
C3—H3	0.96	C16—C17	1.404 (12)
C4—C5	1.532 (12)	C16—C21	1.402 (11)
C4—H4a	0.96	C17—C18	1.385 (14)
C4—H4b	0.96	C18—C19	1.370 (12)
C5—C6	1.539 (13)	C18—H18	0.96
C5—H5a	0.96	C19—C20	1.385 (13)
C5—H5b	0.96	C19—H19	0.96
C6—C7	1.520 (15)	C20—C21	1.380 (13)
C6—H6a	0.96	C21—H21	0.96
C10—O1—H1O	104 (7)	H7a—C7—H7b	110.9091
C17—O2—H2O	101 (6)	N1—C8—C9	111.3 (6)
C1—N1—C2	104.8 (6)	N1—C8—H8a	109.4702
C1—N1—C8	113.0 (6)	N1—C8—H8b	109.4715
C2—N1—C8	112.9 (5)	C9—C8—H8a	109.4718
C1—N2—C3	104.6 (6)	C9—C8—H8b	109.4709
C1—N2—C15	112.3 (6)	H8a—C8—H8b	107.5975
C3—N2—C15	114.1 (7)	C8—C9—C10	121.1 (9)
N1—C1—N2	106.1 (6)	C8—C9—C14	120.8 (7)
N1—C1—H1a	109.4714	C10—C9—C14	118.1 (8)
N1—C1—H1b	109.4713	O1—C10—C9	122.1 (8)
N2—C1—H1a	109.472	O1—C10—C11	117.2 (7)
N2—C1—H1b	109.471	C9—C10—C11	120.7 (9)
H1a—C1—H1b	112.6582	C10—C11—C12	120.0 (8)
N1—C2—C3	101.2 (5)	C10—C11—H11	119.9796
N1—C2—C7	117.1 (7)	C12—C11—H11	119.9777
N1—C2—H2	110.6437	C11—C12—C13	118.9 (9)
C3—C2—C7	110.9 (8)	C11—C12—H12	120.5572
C3—C2—H2	116.8819	C13—C12—H12	120.5582
C7—C2—H2	100.8307	I1—C13—C12	119.8 (7)
N2—C3—C2	101.3 (7)	I1—C13—C14	118.5 (6)
N2—C3—C4	116.5 (7)	C12—C13—C14	121.6 (9)
N2—C3—H3	111.0115	C9—C14—C13	120.7 (7)
C2—C3—C4	111.0 (6)	C9—C14—H14	119.6736
C2—C3—H3	116.5093	C13—C14—H14	119.6733
C4—C3—H3	101.3338	N2—C15—C16	109.9 (8)
C3—C4—C5	107.9 (8)	N2—C15—H15a	109.4717
C3—C4—H4a	109.4721	N2—C15—H15b	109.4717
C3—C4—H4b	109.4725	C16—C15—H15a	109.4703
C5—C4—H4a	109.4701	C16—C15—H15b	109.471
C5—C4—H4b	109.47	H15a—C15—H15b	109.0826
H4a—C4—H4b	111.0366	C15—C16—C17	121.1 (7)
C4—C5—C6	111.8 (9)	C15—C16—C21	121.2 (8)
C4—C5—H5a	109.4716	C17—C16—C21	117.6 (8)
C4—C5—H5b	109.4713	O2—C17—C16	120.0 (8)
C6—C5—H5a	109.4709	O2—C17—C18	119.6 (8)
C6—C5—H5b	109.4715	C16—C17—C18	120.4 (8)
H5a—C5—H5b	107.0854	C17—C18—C19	121.3 (10)
C5—C6—C7	112.5 (6)	C17—C18—H18	119.3262
C5—C6—H6a	109.4704	C19—C18—H18	119.324
C5—C6—H6b	109.4702	C18—C19—C20	119.0 (9)
C7—C6—H6a	109.4723	C18—C19—H19	120.5016
C7—C6—H6b	109.4718	C20—C19—H19	120.5014
H6a—C6—H6b	106.2371	I2—C20—C19	120.4 (7)
C2—C7—C6	108.0 (7)	I2—C20—C21	118.9 (7)
C2—C7—H7a	109.4703	C19—C20—C21	120.7 (8)
C2—C7—H7b	109.4705	C16—C21—C20	120.9 (8)
C6—C7—H7a	109.4719	C16—C21—H21	119.5344
C6—C7—H7b	109.4721	C20—C21—H21	119.5335
?—?—?—?	?

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.84 (10)	1.90 (7)	2.672 (9)	152 (11)
O2—H2O···N2	0.84 (8)	1.91 (8)	2.686 (9)	154 (8)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1	0.84 (10)	1.90 (7)	2.672 (9)	152 (11)
O2—H2O⋯N2	0.84 (8)	1.91 (8)	2.686 (9)	154 (8)