Di-n-propyl 4,4'-dihy-droxy-3,3'-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa-hydro-1H-benzimidazole-1,3-di-yl]bis-(methyl-ene)}dibenzoate.

The title compound, C(29)H(38)N(2)O(6), was prepared as model for studying intra-molecular hydrogen-bonding inter-actions. Mol-ecules of the title compound are located on a crystallographic twofold rotation axis, which passes through the C atom linked to the two N atoms on the imidazolidine ring. The mol-ecular structure shows the existence of two intra-molecular O-H⋯N hydrogen-bonding inter-actions between the two N atoms of the imidazolidine moiety and the hy-droxy groups in the aromatic rings. The crystal structure shows the strain of ring fusion in the perhydro-benzimidazole moiety according to the endocyclic bond angles and the torsion angles, which evidence a puckering of the cyclo-hexane ring with respect to normal tetra-hedral bond angles in an ideal chair conformation.

Related literature

For a related structure, see: Rivera et al. (2010 ▶). For crystallographic data of n-propyl 4-hy­droxy­benzoate, see: Zhou et al. (2010 ▶); Feng & Grant (2006 ▶). For background chemistry to this work, see: Lu et al. (2006 ▶); Geise et al. (1971 ▶). For the synthesis of the precursor, see: Murray-Rust & Riddell (1975 ▶).

Experimental

Crystal data

C29H38N2O6

M = 510.6

Monoclinic,

a = 15.8047 (4) Å

b = 8.7762 (3) Å

c = 19.0108 (6) Å

β = 96.353 (2)°

V = 2620.70 (14) Å3

Z = 4

Cu Kα radiation

μ = 0.73 mm−1

T = 120 K

0.43 × 0.18 × 0.10 mm

Data collection

Agilent Gemini A Ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.638, T max = 1

18471 measured reflections

2339 independent reflections

1855 reflections with I > 3σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.105

S = 1.57

2339 reflections

172 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 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: 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/S1600536811036385/nk2109sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036385/nk2109Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036385/nk2109Isup3.cml

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

C29H38N2O6	F(000) = 1096
Mr = 510.6	Dx = 1.294 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -C 2yc	Cell parameters from 6637 reflections
a = 15.8047 (4) Å	θ = 3.5–67.1°
b = 8.7762 (3) Å	µ = 0.73 mm−1
c = 19.0108 (6) Å	T = 120 K
β = 96.353 (2)°	Plate, colourless
V = 2620.70 (14) Å3	0.43 × 0.18 × 0.10 mm
Z = 4

Agilent Gemini A Ultra diffractometer	2339 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1855 reflections with I > 3σ(I)
mirror	Rint = 0.044
Detector resolution: 10.3784 pixels mm-1	θmax = 67.2°, θmin = 4.7°
Rotation method data acquisition using ω scans	h = −18→18
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −10→9
Tmin = 0.638, Tmax = 1	l = −22→22
18471 measured reflections

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.039	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
wR(F2) = 0.105	(Δ/σ)max = 0.010
S = 1.57	Δρmax = 0.21 e Å−3
2339 reflections	Δρmin = −0.17 e Å−3
172 parameters	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
0 restraints	Extinction coefficient: 1100 (300)
73 constraints

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
O1	0.44235 (7)	0.33457 (13)	0.45643 (6)	0.0351 (4)
O2	0.34718 (6)	0.50352 (12)	0.48867 (5)	0.0273 (3)
O3	0.29215 (7)	−0.02617 (13)	0.70432 (6)	0.0297 (4)
N1	0.44367 (5)	−0.16285 (11)	0.70300 (4)	0.0242 (4)
C1	0.5	−0.06183 (13)	0.75	0.0278 (7)
C2	0.48251 (9)	−0.31564 (17)	0.71167 (8)	0.0242 (5)
C3	0.42460 (9)	−0.45085 (18)	0.69460 (8)	0.0279 (5)
C4	0.47714 (10)	−0.59581 (18)	0.71258 (8)	0.0293 (5)
C5	0.43457 (10)	−0.11400 (18)	0.62864 (8)	0.0278 (5)
C6	0.38601 (9)	0.03362 (18)	0.61649 (7)	0.0246 (4)
C7	0.40693 (9)	0.13502 (18)	0.56533 (8)	0.0251 (5)
C8	0.36156 (9)	0.26911 (18)	0.55025 (7)	0.0245 (5)
C9	0.29302 (9)	0.30241 (17)	0.58796 (8)	0.0248 (5)
C10	0.27134 (9)	0.20348 (18)	0.63976 (8)	0.0262 (5)
C11	0.31679 (9)	0.06936 (18)	0.65395 (8)	0.0251 (4)
C12	0.38833 (9)	0.36954 (18)	0.49413 (8)	0.0257 (5)
C13	0.37042 (9)	0.59939 (18)	0.43146 (8)	0.0279 (5)
C14	0.31759 (10)	0.74213 (19)	0.42731 (8)	0.0327 (5)
C15	0.33797 (12)	0.8368 (2)	0.36391 (10)	0.0401 (6)
H1a	0.533905	−0.000814	0.721944	0.0334*
H2	0.52318	−0.329477	0.678263	0.029*
H3a	0.40456	−0.450366	0.645051	0.0335*
H3b	0.378108	−0.44685	0.723052	0.0335*
H4a	0.440725	−0.683417	0.706234	0.0352*
H4b	0.517975	−0.608248	0.679206	0.0352*
H5a	0.406522	−0.192525	0.599622	0.0334*
H5b	0.489912	−0.103289	0.612879	0.0334*
H7	0.454193	0.112066	0.539465	0.0302*
H9	0.260801	0.394109	0.577963	0.0297*
H10	0.224629	0.227666	0.666045	0.0314*
H13a	0.360587	0.544993	0.387508	0.0335*
H13b	0.429613	0.625746	0.440121	0.0335*
H14a	0.330535	0.800246	0.46993	0.0392*
H14b	0.258305	0.715585	0.42174	0.0392*
H15a	0.302902	0.926349	0.36018	0.0602*
H15b	0.396838	0.866083	0.370217	0.0602*
H15c	0.326969	0.77735	0.321488	0.0602*
H3	0.3366 (14)	−0.095 (2)	0.7126 (10)	0.0446*

	U11	U22	U33	U12	U13	U23
O1	0.0361 (6)	0.0382 (7)	0.0322 (6)	0.0103 (5)	0.0094 (5)	0.0056 (5)
O2	0.0295 (5)	0.0255 (6)	0.0271 (6)	0.0032 (4)	0.0043 (4)	0.0048 (4)
O3	0.0301 (6)	0.0282 (7)	0.0311 (6)	0.0003 (5)	0.0038 (4)	0.0057 (5)
N1	0.0276 (6)	0.0206 (7)	0.0232 (7)	0.0008 (5)	−0.0025 (5)	−0.0003 (5)
C1	0.0318 (11)	0.0226 (12)	0.0277 (11)	0	−0.0024 (9)	0
C2	0.0267 (7)	0.0210 (8)	0.0245 (8)	0.0026 (6)	0.0013 (6)	0.0006 (6)
C3	0.0300 (8)	0.0246 (9)	0.0278 (8)	−0.0012 (6)	−0.0029 (6)	−0.0015 (6)
C4	0.0354 (8)	0.0203 (8)	0.0318 (9)	−0.0009 (6)	0.0009 (7)	−0.0023 (6)
C5	0.0340 (8)	0.0259 (9)	0.0226 (8)	0.0050 (7)	−0.0010 (6)	−0.0002 (6)
C6	0.0265 (7)	0.0237 (8)	0.0219 (7)	0.0026 (6)	−0.0047 (6)	−0.0034 (6)
C7	0.0261 (7)	0.0274 (9)	0.0213 (8)	0.0036 (6)	−0.0002 (6)	−0.0027 (6)
C8	0.0262 (7)	0.0247 (8)	0.0214 (7)	−0.0002 (6)	−0.0026 (6)	−0.0018 (6)
C9	0.0244 (7)	0.0219 (8)	0.0267 (8)	0.0025 (6)	−0.0029 (6)	−0.0033 (6)
C10	0.0228 (7)	0.0280 (9)	0.0276 (8)	0.0001 (6)	0.0018 (6)	−0.0021 (6)
C11	0.0265 (7)	0.0258 (9)	0.0219 (7)	−0.0032 (6)	−0.0021 (6)	−0.0010 (6)
C12	0.0267 (7)	0.0265 (9)	0.0226 (8)	0.0024 (6)	−0.0027 (6)	−0.0002 (6)
C13	0.0270 (7)	0.0306 (9)	0.0263 (8)	−0.0012 (6)	0.0036 (6)	0.0071 (7)
C14	0.0389 (9)	0.0289 (9)	0.0313 (9)	0.0029 (7)	0.0087 (7)	0.0033 (7)
C15	0.0486 (10)	0.0339 (10)	0.0400 (10)	0.0082 (8)	0.0147 (8)	0.0097 (8)

O1—C12	1.2134 (19)	C5—H5b	0.96
O2—C12	1.3422 (19)	C6—C7	1.385 (2)
O2—C13	1.4539 (19)	C6—C11	1.405 (2)
O3—C11	1.3615 (19)	C7—C8	1.391 (2)
O3—H3	0.93 (2)	C7—H7	0.96
N1—C1	1.4835 (11)	C8—C9	1.395 (2)
N1—C2	1.4763 (17)	C8—C12	1.481 (2)
N1—C5	1.4689 (17)	C9—C10	1.384 (2)
C1—H1a	0.96	C9—H9	0.96
C1—H1ai	0.96	C10—C11	1.390 (2)
C2—C2i	1.500 (2)	C10—H10	0.96
C2—C3	1.512 (2)	C13—C14	1.503 (2)
C2—H2	0.96	C13—H13a	0.96
C3—C4	1.537 (2)	C13—H13b	0.96
C3—H3a	0.96	C14—C15	1.527 (3)
C3—H3b	0.96	C14—H14a	0.96
C4—C4i	1.523 (2)	C14—H14b	0.96
C4—H4a	0.96	C15—H15a	0.96
C4—H4b	0.96	C15—H15b	0.96
C5—C6	1.511 (2)	C15—H15c	0.96
C5—H5a	0.96
C12—O2—C13	113.86 (12)	C7—C6—C11	118.18 (14)
C11—O3—H3	104.6 (13)	C6—C7—C8	122.04 (14)
C1—N1—C2	105.14 (8)	C6—C7—H7	118.9808
C1—N1—C5	113.18 (9)	C8—C7—H7	118.9799
C2—N1—C5	111.58 (10)	C7—C8—C9	118.90 (14)
N1—C1—N1i	106.60 (9)	C7—C8—C12	118.03 (13)
N1—C1—H1a	109.4712	C9—C8—C12	123.07 (14)
N1—C1—H1ai	109.4713	C8—C9—C10	120.12 (14)
N1i—C1—H1a	109.4713	C8—C9—H9	119.9408
N1i—C1—H1ai	109.4712	C10—C9—H9	119.9415
H1a—C1—H1ai	112.196	C9—C10—C11	120.42 (14)
N1—C2—C2i	102.26 (11)	C9—C10—H10	119.7917
N1—C2—C3	117.04 (11)	C11—C10—H10	119.7918
N1—C2—H2	109.9711	O3—C11—C6	121.21 (13)
C2i—C2—C3	110.96 (12)	O3—C11—C10	118.45 (13)
C2i—C2—H2	116.1607	C6—C11—C10	120.34 (14)
C3—C2—H2	101.0977	O1—C12—O2	122.85 (14)
C2—C3—C4	107.61 (12)	O1—C12—C8	123.42 (14)
C2—C3—H3a	109.4708	O2—C12—C8	113.73 (13)
C2—C3—H3b	109.4712	O2—C13—C14	109.68 (13)
C4—C3—H3a	109.4711	O2—C13—H13a	109.4707
C4—C3—H3b	109.4719	O2—C13—H13b	109.4714
H3a—C3—H3b	111.2673	C14—C13—H13a	109.4706
C3—C4—C4i	113.37 (13)	C14—C13—H13b	109.4711
C3—C4—H4a	109.4715	H13a—C13—H13b	109.2656
C3—C4—H4b	109.4718	C13—C14—C15	109.29 (14)
C4i—C4—H4a	109.4713	C13—C14—H14a	109.4708
C4i—C4—H4b	109.4702	C13—C14—H14b	109.4715
H4a—C4—H4b	105.271	C15—C14—H14a	109.4706
N1—C5—C6	113.04 (12)	C15—C14—H14b	109.4717
N1—C5—H5a	109.4711	H14a—C14—H14b	109.6526
N1—C5—H5b	109.4709	C14—C15—H15a	109.4714
C6—C5—H5a	109.4723	C14—C15—H15b	109.4714
C6—C5—H5b	109.471	C14—C15—H15c	109.4713
H5a—C5—H5b	105.6475	H15a—C15—H15b	109.4713
C5—C6—C7	120.11 (13)	H15a—C15—H15c	109.4713
C5—C6—C11	121.66 (13)	H15b—C15—H15c	109.4708
?—?—?—?	?

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1	0.93 (2)	1.82 (2)	2.6810 (14)	153 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1	0.93 (2)	1.82 (2)	2.6810 (14)	153 (2)