2,2'-[(3aRS,7aRS)-Perhydro-benz-imid-azole-1,3-di-yl)bis-(methyl-ene)]diphenol.

The molecular structure of the title compound, C(21)H(26)N(2)O(2), shows two intra-molecular O-H⋯N hydrogen-bonding inter-actions. In the crystal structure, mol-ecular chains are formed along the c axis through weak C-H⋯O inter-actions. Neighbouring chains are weakly associated along the a axis via C-H⋯π inter-actions.

Related literature

For a related structure, see: Rivera et al. (2009 ▶). For uses of di-Mannich bases, see Mitra et al. (2006 ▶); Elias et al. (1997 ▶).

Experimental

Crystal data

C21H26N2O2

M = 338.5

Triclinic,

a = 5.5177 (1) Å

b = 12.0432 (4) Å

c = 14.3752 (4) Å

α = 69.705 (3)°

β = 89.341 (2)°

γ = 81.751 (2)°

V = 885.92 (5) Å3

Z = 2

Cu Kα radiation

μ = 0.65 mm−1

T = 120 K

0.24 × 0.21 × 0.19 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 = 0.774, T max = 1.000

11989 measured reflections

3023 independent reflections

2685 reflections with I > 3σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.118

S = 2.41

3023 reflections

232 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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/S1600536810009918/tk2643sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009918/tk2643Isup2.hkl

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

C21H26N2O2	Z = 2
Mr = 338.5	F(000) = 364
Triclinic, P1	Dx = 1.268 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 5.5177 (1) Å	Cell parameters from 9142 reflections
b = 12.0432 (4) Å	θ = 3.3–65.4°
c = 14.3752 (4) Å	µ = 0.65 mm−1
α = 69.705 (3)°	T = 120 K
β = 89.341 (2)°	Prism, colorless
γ = 81.751 (2)°	0.24 × 0.21 × 0.19 mm
V = 885.92 (5) Å3

Oxford Diffraction Xcalibur, diffractometer with an Atlas (Gemini ultra Cu) detector	3023 independent reflections
Radiation source: X-ray tube	2685 reflections with I > 3σ(I)
mirror	Rint = 0.018
Detector resolution: 10.3784 pixels mm-1	θmax = 65.8°, θmin = 3.3°
Rotation method data acquisition using ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→13
Tmin = 0.774, Tmax = 1.000	l = −16→16
11989 measured reflections

Refinement on F2	98 constraints
R[F2 > 2σ(F2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
S = 2.41	(Δ/σ)max = 0.006
3023 reflections	Δρmax = 0.25 e Å−3
232 parameters	Δρmin = −0.19 e Å−3
0 restraints

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	0.55804 (17)	0.14020 (9)	0.44644 (7)	0.0291 (4)
O2	0.83868 (17)	0.18264 (9)	−0.03369 (7)	0.0305 (4)
N1	0.79361 (18)	0.08554 (9)	0.29799 (7)	0.0202 (4)
N2	0.62975 (19)	0.10318 (10)	0.14258 (7)	0.0213 (4)
C1	0.6914 (2)	0.17421 (12)	0.20218 (9)	0.0226 (5)
C2	0.9951 (2)	0.12344 (12)	0.33988 (9)	0.0226 (5)
C3	0.9035 (2)	0.23158 (11)	0.36752 (9)	0.0216 (4)
C4	0.6882 (2)	0.23380 (12)	0.42039 (9)	0.0227 (4)
C5	0.6072 (2)	0.33136 (12)	0.44923 (9)	0.0261 (5)
C6	0.7390 (2)	0.42599 (13)	0.42654 (10)	0.0289 (5)
C7	0.9518 (2)	0.42527 (13)	0.37409 (10)	0.0289 (5)
C8	1.0308 (2)	0.32828 (12)	0.34497 (10)	0.0254 (5)
C9	0.8513 (2)	−0.02791 (11)	0.27990 (9)	0.0210 (4)
C10	0.8803 (2)	−0.14204 (12)	0.36961 (9)	0.0265 (5)
C11	0.9041 (3)	−0.24770 (13)	0.33239 (10)	0.0295 (5)
C12	0.6923 (3)	−0.23872 (12)	0.26116 (10)	0.0295 (5)
C13	0.6592 (2)	−0.11997 (12)	0.17294 (10)	0.0259 (5)
C14	0.6331 (2)	−0.01887 (11)	0.21374 (9)	0.0207 (4)
C15	0.4060 (2)	0.15656 (12)	0.07972 (9)	0.0231 (5)
C16	0.4414 (2)	0.27197 (12)	−0.00170 (9)	0.0220 (4)
C17	0.6553 (2)	0.27821 (12)	−0.05575 (9)	0.0242 (5)
C18	0.6825 (3)	0.38203 (13)	−0.13478 (10)	0.0297 (5)
C19	0.4978 (3)	0.47854 (13)	−0.16005 (10)	0.0322 (5)
C20	0.2872 (3)	0.47453 (13)	−0.10655 (10)	0.0321 (5)
C21	0.2613 (2)	0.37168 (13)	−0.02762 (10)	0.0273 (5)
H1a	0.544692	0.22078	0.213055	0.0271*
H1b	0.814039	0.221818	0.169948	0.0271*
H2a	1.119524	0.142433	0.292045	0.0271*
H2b	1.066463	0.059026	0.397776	0.0271*
H5	0.459427	0.332936	0.484953	0.0313*
H6	0.683126	0.492726	0.447191	0.0347*
H7	1.042987	0.491174	0.358217	0.0346*
H8	1.177255	0.328004	0.308288	0.0304*
H9	1.010365	−0.035487	0.253016	0.0252*
H10a	0.737945	−0.142807	0.408735	0.0318*
H10b	1.025945	−0.147212	0.407689	0.0318*
H11a	0.912941	−0.321113	0.388014	0.0353*
H11b	1.056388	−0.252589	0.300031	0.0353*
H12a	0.543303	−0.246619	0.296477	0.0354*
H12b	0.720963	−0.304289	0.237045	0.0354*
H13a	0.800881	−0.116292	0.133191	0.031*
H13b	0.513586	−0.113908	0.134504	0.031*
H14	0.478413	−0.028884	0.244425	0.0249*
H15a	0.273969	0.172023	0.119698	0.0277*
H15b	0.361755	0.10108	0.050763	0.0277*
H18	0.829452	0.386296	−0.171479	0.0356*
H19	0.515368	0.549372	−0.215424	0.0386*
H20	0.160216	0.542534	−0.124022	0.0386*
H21	0.115837	0.369273	0.009909	0.0328*
H1o	0.604 (3)	0.0973 (15)	0.4118 (12)	0.0349*
H2o	0.810 (3)	0.1344 (15)	0.0240 (13)	0.0366*

	U11	U22	U33	U12	U13	U23
O1	0.0304 (5)	0.0306 (6)	0.0309 (6)	−0.0103 (4)	0.0112 (4)	−0.0146 (4)
O2	0.0248 (5)	0.0374 (6)	0.0250 (5)	−0.0010 (4)	0.0063 (4)	−0.0072 (4)
N1	0.0204 (5)	0.0221 (6)	0.0178 (5)	−0.0029 (4)	−0.0004 (4)	−0.0065 (4)
N2	0.0215 (6)	0.0241 (6)	0.0173 (5)	−0.0028 (4)	−0.0008 (4)	−0.0061 (4)
C1	0.0236 (7)	0.0238 (7)	0.0200 (7)	−0.0034 (5)	0.0002 (5)	−0.0069 (5)
C2	0.0198 (6)	0.0279 (7)	0.0216 (7)	−0.0042 (5)	0.0002 (5)	−0.0101 (5)
C3	0.0204 (6)	0.0270 (7)	0.0161 (6)	−0.0012 (5)	−0.0029 (5)	−0.0067 (5)
C4	0.0230 (6)	0.0269 (7)	0.0177 (6)	−0.0045 (5)	−0.0006 (5)	−0.0068 (5)
C5	0.0239 (7)	0.0317 (8)	0.0231 (7)	−0.0014 (5)	0.0020 (5)	−0.0112 (6)
C6	0.0321 (7)	0.0271 (8)	0.0282 (7)	0.0006 (6)	−0.0014 (6)	−0.0124 (6)
C7	0.0305 (7)	0.0278 (7)	0.0294 (7)	−0.0085 (6)	−0.0003 (6)	−0.0098 (6)
C8	0.0215 (7)	0.0304 (8)	0.0239 (7)	−0.0042 (5)	0.0012 (5)	−0.0089 (6)
C9	0.0195 (6)	0.0251 (7)	0.0198 (6)	−0.0033 (5)	0.0027 (5)	−0.0097 (5)
C10	0.0292 (7)	0.0266 (7)	0.0214 (7)	−0.0021 (6)	−0.0025 (5)	−0.0061 (6)
C11	0.0333 (8)	0.0239 (7)	0.0285 (7)	−0.0024 (6)	−0.0004 (6)	−0.0066 (6)
C12	0.0320 (8)	0.0258 (8)	0.0321 (7)	−0.0041 (6)	0.0000 (6)	−0.0118 (6)
C13	0.0254 (7)	0.0292 (7)	0.0245 (7)	−0.0025 (5)	−0.0020 (5)	−0.0119 (6)
C14	0.0193 (6)	0.0239 (7)	0.0188 (6)	−0.0034 (5)	0.0033 (5)	−0.0071 (5)
C15	0.0197 (6)	0.0295 (7)	0.0186 (6)	−0.0031 (5)	0.0003 (5)	−0.0068 (5)
C16	0.0225 (6)	0.0276 (7)	0.0160 (6)	−0.0050 (5)	−0.0022 (5)	−0.0073 (5)
C17	0.0226 (7)	0.0315 (8)	0.0197 (6)	−0.0043 (5)	−0.0012 (5)	−0.0103 (6)
C18	0.0279 (7)	0.0399 (8)	0.0220 (7)	−0.0132 (6)	0.0034 (5)	−0.0086 (6)
C19	0.0403 (8)	0.0296 (8)	0.0245 (7)	−0.0136 (6)	−0.0028 (6)	−0.0034 (6)
C20	0.0354 (8)	0.0282 (8)	0.0297 (8)	−0.0025 (6)	−0.0045 (6)	−0.0069 (6)
C21	0.0245 (7)	0.0331 (8)	0.0241 (7)	−0.0029 (6)	0.0008 (5)	−0.0104 (6)

O1—C4	1.3640 (17)	C9—H9	0.96
O1—H1o	0.85 (2)	C10—C11	1.531 (2)
O2—C17	1.3672 (15)	C10—H10a	0.96
O2—H2o	0.860 (16)	C10—H10b	0.96
N1—C1	1.4766 (14)	C11—C12	1.530 (2)
N1—C2	1.4691 (19)	C11—H11a	0.96
N1—C9	1.4682 (19)	C11—H11b	0.96
N2—C1	1.476 (2)	C12—C13	1.5360 (17)
N2—C14	1.4686 (15)	C12—H12a	0.96
N2—C15	1.4657 (15)	C12—H12b	0.96
C1—H1a	0.96	C13—C14	1.513 (2)
C1—H1b	0.96	C13—H13a	0.96
C2—C3	1.508 (2)	C13—H13b	0.96
C2—H2a	0.96	C14—H14	0.96
C2—H2b	0.96	C15—C16	1.5112 (17)
C3—C4	1.4045 (18)	C15—H15a	0.96
C3—C8	1.387 (2)	C15—H15b	0.96
C4—C5	1.391 (2)	C16—C17	1.4021 (18)
C5—C6	1.382 (2)	C16—C21	1.3873 (18)
C5—H5	0.96	C17—C18	1.3932 (17)
C6—C7	1.388 (2)	C18—C19	1.3774 (19)
C6—H6	0.96	C18—H18	0.96
C7—C8	1.385 (2)	C19—C20	1.383 (2)
C7—H7	0.96	C19—H19	0.96
C8—H8	0.96	C20—C21	1.3836 (18)
C9—C10	1.5132 (16)	C20—H20	0.96
C9—C14	1.5110 (18)	C21—H21	0.96
C4—O1—H1o	108.2 (12)	H10a—C10—H10b	111.0115
C17—O2—H2o	106.1 (11)	C10—C11—C12	112.84 (11)
C1—N1—C2	113.14 (10)	C10—C11—H11a	109.4701
C1—N1—C9	105.19 (10)	C10—C11—H11b	109.4716
C2—N1—C9	116.16 (9)	C12—C11—H11a	109.4715
C1—N2—C14	105.33 (9)	C12—C11—H11b	109.4714
C1—N2—C15	113.32 (10)	H11a—C11—H11b	105.8786
C14—N2—C15	116.36 (10)	C11—C12—C13	112.18 (12)
N1—C1—N2	105.37 (10)	C11—C12—H12a	109.4714
N1—C1—H1a	109.4708	C11—C12—H12b	109.4713
N1—C1—H1b	109.4714	C13—C12—H12a	109.4711
N2—C1—H1a	109.4714	C13—C12—H12b	109.4709
N2—C1—H1b	109.4717	H12a—C12—H12b	106.6143
H1a—C1—H1b	113.2791	C12—C13—C14	108.00 (11)
N1—C2—C3	110.68 (10)	C12—C13—H13a	109.4714
N1—C2—H2a	109.4709	C12—C13—H13b	109.4718
N1—C2—H2b	109.4709	C14—C13—H13a	109.4704
C3—C2—H2a	109.4716	C14—C13—H13b	109.4706
C3—C2—H2b	109.4715	H13a—C13—H13b	110.8996
H2a—C2—H2b	108.2321	N2—C14—C9	100.17 (10)
C2—C3—C4	119.73 (12)	N2—C14—C13	117.53 (10)
C2—C3—C8	121.68 (11)	N2—C14—H14	111.415
C4—C3—C8	118.55 (13)	C9—C14—C13	111.83 (10)
O1—C4—C3	121.18 (13)	C9—C14—H14	117.1568
O1—C4—C5	118.71 (12)	C13—C14—H14	99.6523
C3—C4—C5	120.10 (13)	N2—C15—C16	111.17 (11)
C4—C5—C6	120.11 (13)	N2—C15—H15a	109.4717
C4—C5—H5	119.9469	N2—C15—H15b	109.4711
C6—C5—H5	119.9479	C16—C15—H15a	109.4714
C5—C6—C7	120.49 (15)	C16—C15—H15b	109.4709
C5—C6—H6	119.7554	H15a—C15—H15b	107.7171
C7—C6—H6	119.7553	C15—C16—C17	119.99 (11)
C6—C7—C8	119.18 (14)	C15—C16—C21	121.39 (11)
C6—C7—H7	120.41	C17—C16—C21	118.57 (11)
C8—C7—H7	120.4116	O2—C17—C16	121.12 (10)
C3—C8—C7	121.58 (12)	O2—C17—C18	118.62 (11)
C3—C8—H8	119.211	C16—C17—C18	120.25 (11)
C7—C8—H8	119.2111	C17—C18—C19	119.75 (12)
N1—C9—C10	117.23 (11)	C17—C18—H18	120.1267
N1—C9—C14	100.32 (9)	C19—C18—H18	120.1261
N1—C9—H9	111.4609	C18—C19—C20	120.74 (12)
C10—C9—C14	111.72 (11)	C18—C19—H19	119.6301
C10—C9—H9	99.994	C20—C19—H19	119.6303
C14—C9—H9	116.9901	C19—C20—C21	119.43 (12)
C9—C10—C11	107.89 (11)	C19—C20—H20	120.2825
C9—C10—H10a	109.4713	C21—C20—H20	120.2833
C9—C10—H10b	109.4707	C16—C21—C20	121.24 (13)
C11—C10—H10a	109.4714	C16—C21—H21	119.3796
C11—C10—H10b	109.4712	C20—C21—H21	119.3801
?—?—?—?	?

Cg1 and Cg2 are the centroids of the C3–C8 and C16–C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.847 (18)	1.967 (17)	2.7096 (14)	145.8 (16)
O2—H2O···N2	0.860 (18)	1.913 (17)	2.6894 (14)	149.5 (17)
C10—H10a···O1i	0.96	2.64	3.5666 (17)	163
C13—H13a···O2ii	0.96	2.63	3.5458 (17)	160
C10—H10b···Cg1iii	0.96	2.94	3.5885 (13)	126
C12—H12b···Cg2iv	0.96	2.93	3.7022 (16)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C3–C8 and C16–C21 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1	0.85 (2)	1.97 (2)	2.7096 (14)	146 (2)
O2—H2O⋯N2	0.86 (2)	1.91 (2)	2.6894 (14)	150 (2)
C10—H10a⋯O1i	0.96	2.64	3.5666 (17)	163
C13—H13a⋯O2ii	0.96	2.63	3.5458 (17)	160
C10—H10b⋯Cg1iii	0.96	2.94	3.5885 (13)	126
C12—H12b⋯Cg2iv	0.96	2.93	3.7022 (16)	139

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .