4,4'-Dichloro-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.

Mol-ecules of the the title compound, C(21)H(24)Cl(2)N(2)O(2), are located on a twofold rotation axis, which passes through the C atom linking the two N atoms. Two intra-molecular O-H⋯N hydrogen bonds were observed. In the crystal, non-classical inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains along the a axis. The crystal studied was a racemic twin.

Related literature

For related structures, see: Rivera et al. (2009 ▶, 2010 ▶). For uses of di-Mannich bases, see: Mitra et al. (2006 ▶); Elias et al. (1997 ▶). For the anti­malarial activity of di-Mannich bases, see: Shanks & Edstein (2005 ▶).

Experimental

Crystal data

C21H24Cl2N2O2

M = 407.3

Orthorhombic,

a = 5.9529 (2) Å

b = 18.3846 (5) Å

c = 8.9704 (3) Å

V = 981.74 (5) Å3

Z = 2

Cu Kα radiation

μ = 3.11 mm−1

T = 120 K

0.36 × 0.21 × 0.12 mm

Data collection

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

Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.518, T max = 0.773

12720 measured reflections

1566 independent reflections

1517 reflections with I > 3σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.068

S = 1.50

1566 reflections

127 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.11 e Å−3

Δρmin = −0.11 e Å−3

Absolute structure: Flack (1983 ▶), 615 Friedel pairs

Flack parameter: 0.32 (1)

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/S160053681003792X/bt5333sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003792X/bt5333Isup2.hkl

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

C21H24Cl2N2O2	F(000) = 428
Mr = 407.3	Dx = 1.378 Mg m−3
Orthorhombic, P21212	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2 2ab	Cell parameters from 10371 reflections
a = 5.9529 (2) Å	θ = 4.8–62.4°
b = 18.3846 (5) Å	µ = 3.11 mm−1
c = 8.9704 (3) Å	T = 120 K
V = 981.74 (5) Å3	Irregular shape, colorless
Z = 2	0.36 × 0.21 × 0.12 mm

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	1566 independent reflections
Radiation source: X-ray tube	1517 reflections with I > 3σ(I)
mirror	Rint = 0.027
Detector resolution: 10.3784 pixels mm-1	θmax = 62.5°, θmin = 4.8°
Rotation method data acquisition using ω scans	h = −6→6
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	k = −21→20
Tmin = 0.518, Tmax = 0.773	l = −10→10
12720 measured reflections

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.022	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
wR(F2) = 0.068	(Δ/σ)max = 0.010
S = 1.50	Δρmax = 0.11 e Å−3
1566 reflections	Δρmin = −0.11 e Å−3
127 parameters	Absolute structure: Flack (1983), 615 Friedel pairs
0 restraints	Flack parameter: 0.32 (1)
45 constraints

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.51 (release 27-10-2009 CrysAlis171 .NET) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)Physical MeasurementsThe melting point was determined with an Electrothermal apparatus, and it has not been corrected. IR spectrum was recorded as KBr pellets at 292 K on a Perkin-Elmer Paragon FT-IR instrument. NMR spectra were performed in CDCl3 at room temperature on a Bruker AMX 400 Advance spectrometer.

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	0.56453 (8)	0.22892 (2)	0.85004 (4)	0.03657 (14)
O1	0.99889 (19)	0.41865 (6)	0.41066 (13)	0.0278 (3)
N1	0.59603 (9)	0.44360 (5)	0.29542 (10)	0.0191 (4)
C1	0.5	0.5	0.39535 (12)	0.0190 (6)
C2	0.5511 (3)	0.36844 (7)	0.34499 (16)	0.0207 (4)
C3	0.6738 (3)	0.34996 (7)	0.48640 (16)	0.0188 (4)
C4	0.8923 (2)	0.37633 (8)	0.51184 (18)	0.0208 (4)
C5	1.0043 (3)	0.35815 (8)	0.64297 (17)	0.0260 (5)
C6	0.9061 (3)	0.31220 (8)	0.74665 (18)	0.0266 (5)
C7	0.6930 (3)	0.28560 (8)	0.71952 (17)	0.0244 (5)
C8	0.5774 (3)	0.30421 (7)	0.59086 (16)	0.0204 (4)
C9	0.5027 (2)	0.45884 (7)	0.14700 (16)	0.0214 (4)
C10	0.6300 (3)	0.43023 (9)	0.01323 (18)	0.0313 (5)
C11	0.5134 (3)	0.45859 (9)	−0.12729 (18)	0.0387 (6)
H1a	0.382262	0.478981	0.454451	0.0228*
H2a	0.392563	0.362122	0.359869	0.0249*
H2b	0.594229	0.335034	0.267886	0.0249*
H5	1.151137	0.37767	0.661739	0.0312*
H6	0.984963	0.299065	0.836016	0.0319*
H8	0.429374	0.285198	0.574125	0.0245*
H9	0.361614	0.434259	0.134648	0.0257*
H10a	0.626351	0.378021	0.013612	0.0375*
H10b	0.781744	0.447839	0.016012	0.0375*
H11a	0.368381	0.436182	−0.136609	0.0464*
H11b	0.597131	0.443924	−0.213654	0.0464*
H1o	0.893 (3)	0.4356 (10)	0.347 (2)	0.0334*

	U11	U22	U33	U12	U13	U23
Cl1	0.0514 (3)	0.0328 (2)	0.0254 (2)	−0.00039 (19)	0.00732 (18)	0.00639 (15)
O1	0.0191 (5)	0.0233 (5)	0.0410 (6)	−0.0026 (4)	0.0007 (5)	0.0049 (5)
N1	0.0231 (6)	0.0132 (6)	0.0208 (6)	0.0018 (5)	0.0003 (5)	0.0012 (5)
C1	0.0188 (10)	0.0153 (9)	0.0231 (10)	−0.0004 (8)	0	0
C2	0.0217 (7)	0.0140 (6)	0.0264 (8)	−0.0016 (6)	−0.0020 (7)	−0.0004 (6)
C3	0.0200 (7)	0.0116 (6)	0.0249 (8)	0.0028 (6)	−0.0009 (6)	−0.0019 (6)
C4	0.0173 (7)	0.0150 (6)	0.0300 (9)	0.0027 (5)	0.0017 (6)	−0.0035 (6)
C5	0.0200 (8)	0.0239 (7)	0.0341 (9)	0.0039 (6)	−0.0053 (7)	−0.0055 (7)
C6	0.0314 (9)	0.0230 (7)	0.0253 (8)	0.0095 (7)	−0.0050 (7)	−0.0058 (6)
C7	0.0339 (9)	0.0179 (7)	0.0213 (8)	0.0045 (7)	0.0050 (7)	−0.0005 (6)
C8	0.0204 (7)	0.0142 (6)	0.0267 (7)	0.0010 (6)	0.0021 (6)	−0.0023 (6)
C9	0.0246 (8)	0.0177 (8)	0.0218 (7)	0.0029 (5)	−0.0014 (6)	−0.0014 (6)
C10	0.0446 (10)	0.0239 (8)	0.0253 (9)	0.0088 (7)	0.0027 (8)	−0.0020 (7)
C11	0.0611 (13)	0.0322 (10)	0.0229 (8)	0.0134 (8)	−0.0012 (9)	−0.0039 (7)

Cl1—C7	1.7441 (16)	C5—H5	0.96
O1—C4	1.3535 (19)	C6—C7	1.381 (2)
O1—H1o	0.91 (2)	C6—H6	0.96
N1—C1	1.4850 (11)	C7—C8	1.386 (2)
N1—C2	1.4761 (16)	C8—H8	0.96
N1—C9	1.4697 (17)	C9—C9i	1.5138 (19)
C1—H1a	0.96	C9—C10	1.514 (2)
C1—H1ai	0.96	C9—H9	0.96
C2—C3	1.503 (2)	C10—C11	1.531 (2)
C2—H2a	0.96	C10—H10a	0.96
C2—H2b	0.96	C10—H10b	0.96
C3—C4	1.406 (2)	C11—C11i	1.531 (2)
C3—C8	1.384 (2)	C11—H11a	0.96
C4—C5	1.393 (2)	C11—H11b	0.96
C5—C6	1.386 (2)
C4—O1—H1o	106.9 (12)	C5—C6—H6	120.4925
C1—N1—C2	113.70 (8)	C7—C6—H6	120.4933
C1—N1—C9	105.56 (8)	Cl1—C7—C6	119.74 (12)
C2—N1—C9	112.50 (9)	Cl1—C7—C8	119.24 (12)
N1—C1—N1i	105.74 (8)	C6—C7—C8	121.01 (14)
N1—C1—H1a	109.4709	C3—C8—C7	120.52 (14)
N1—C1—H1ai	109.4712	C3—C8—H8	119.7416
N1i—C1—H1a	109.4713	C7—C8—H8	119.7416
N1i—C1—H1ai	109.4709	N1—C9—C9i	101.45 (10)
H1a—C1—H1ai	112.9619	N1—C9—C10	117.56 (12)
N1—C2—C3	112.19 (11)	N1—C9—H9	110.2149
N1—C2—H2a	109.4717	C9i—C9—C10	110.98 (12)
N1—C2—H2b	109.4705	C9i—C9—H9	116.8873
C3—C2—H2a	109.4714	C10—C9—H9	100.538
C3—C2—H2b	109.4717	C9—C10—C11	107.90 (14)
H2a—C2—H2b	106.6084	C9—C10—H10a	109.4715
C2—C3—C4	120.58 (13)	C9—C10—H10b	109.4705
C2—C3—C8	120.48 (13)	C11—C10—H10a	109.4721
C4—C3—C8	118.88 (14)	C11—C10—H10b	109.4708
O1—C4—C3	121.52 (14)	H10a—C10—H10b	110.9991
O1—C4—C5	118.68 (13)	C10—C11—C11i	112.71 (13)
C3—C4—C5	119.80 (14)	C10—C11—H11a	109.4707
C4—C5—C6	120.75 (14)	C10—C11—H11b	109.4709
C4—C5—H5	119.6278	C11i—C11—H11a	109.472
C6—C5—H5	119.6266	C11i—C11—H11b	109.4712
C5—C6—C7	119.01 (15)	H11a—C11—H11b	106.0299
?—?—?—?	?

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1a···O1ii	0.95	2.56	3.3398 (11)	137.58
O1—H1o···N1	0.91 (2)	1.83 (2)	2.6515 (13)	149.3 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1a⋯O1i	0.95	2.56	3.3398 (11)	137.58
O1—H1o⋯N1	0.91 (2)	1.83 (2)	2.6515 (13)	149.3 (18)

Symmetry code: (i) .