rac-4-Chloro-2-[({2-[(3-chloro-6-hy-droxy-2,4-dimethyl-benz-yl)(meth-yl)amino]-prop-yl}(meth-yl)amino)-meth-yl]-3,5-dimethyl-phenol.

The title compound, C(23)H(32)Cl(2)N(2)O(2), a potential chiral ligand for coordination chemistry, was prepared by a two-step reaction. The mol-ecule is located on a crystallographic centre of inversion. As a result, the methyl group bonded to the methyl-ene group is disordered over two equally occupied positions, sharing the same site as the H atom of the chiral C atom. As a further consequence of the crystallographic centrosymmetry, the 1,2-diamino-propane unit adopts an anti-periplanar conformation and the two benzene rings are coplanar. The central chain is in an all-trans arrangement. An intra-molecular O-H⋯N hydrogen bond makes an S(6) ring motif. A C-H⋯π inter-action links the mol-ecules into one-dimensional chains along the [001] direction.

Related literature

For the synthesis of the title compound, see: Rivera et al. (2010 ▶); Burke (1949 ▶). For the uses of tetra­hydro­salens in coordination chemistry, see: Atwood (1997 ▶). For related structures, see: Rivera et al. (2011 ▶); Xu et al. (2009 ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C23H32Cl2N2O2

M = 439.41

Monoclinic,

a = 9.5011 (8) Å

b = 11.9060 (13) Å

c = 9.9824 (9) Å

β = 90.348 (7)°

V = 1129.19 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.31 mm−1

T = 173 K

0.25 × 0.22 × 0.08 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001 ▶) T min = 0.927, T max = 0.976

11151 measured reflections

2055 independent reflections

1758 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.159

S = 1.14

2055 reflections

144 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.35 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812039694/go2069sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039694/go2069Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039694/go2069Isup3.cml

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

C23H32Cl2N2O2	F(000) = 468
Mr = 439.41	Dx = 1.292 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 11821 reflections
a = 9.5011 (8) Å	θ = 2.4–28.1°
b = 11.9060 (13) Å	µ = 0.31 mm−1
c = 9.9824 (9) Å	T = 173 K
β = 90.348 (7)°	Plate, colourless
V = 1129.19 (19) Å3	0.25 × 0.22 × 0.08 mm
Z = 2

Stoe IPDS II two-circle diffractometer	2055 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	1758 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.074
ω scans	θmax = 25.3°, θmin = 3.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −11→11
Tmin = 0.927, Tmax = 0.976	k = −14→14
11151 measured reflections	l = −11→11

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ2(Fo2) + (0.0629P)2 + 0.952P] where P = (Fo2 + 2Fc2)/3
2055 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Experimental. 1H NMR (400.1 MHz, CDCl3): δ 1.07 (d, 3J = 6.6 Hz, 3H), 2.18 (s, 3H),2.25 (s, 3H), 2.30 (s, 6H), 2.31 (s, 6H), 2.35 (dd, 2Jgem = 12.6, 3J = 6.9 Hz, 1H), 2.62 (dd, 2Jgem = 12.6, 3J = 6.7 Hz, 1H), 3.03–3.11 (m, 1H), 3.69 (d, 2Jgem = 14.0, 1H), 3.74 (d, 2Jgem = 14.0, 1H), 3.81 (s, 2H), 6.62 (s, 2H) 13C NMR (100.6 MHz, CDCl3): δ 11.17, 16.74, 16.82, 21.22, 21.24, 35.19, 41.9, 53.68, 54.20, 58.57, 60.32, 116.57, 116.58, 118.48, 118.94, 125.26, 125.39, 133.96, 134.04, 136.62, 136.73, 156.76, 156.78. F T—IR (KBr) (ν, cm-1): 3406 (O—H, broad, m), 2960 (CH3asym, st), 2922 (CH2asym, st), 2855 (CH3sym, st), 2802 (CH2sym, st), 1613 (–C=C, st), 1320 (C—N, st), 668 (C—Cl, st).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.74219 (10)	0.71021 (8)	0.25120 (9)	0.0590 (3)
N1	0.5987 (3)	0.54354 (18)	0.8459 (2)	0.0383 (6)
O1	0.7205 (2)	0.39166 (17)	0.6972 (3)	0.0485 (6)
H1	0.687 (5)	0.421 (4)	0.764 (5)	0.071 (13)*
C1	0.5450 (3)	0.5882 (3)	0.7189 (3)	0.0410 (7)
H1A	0.5303	0.6702	0.7282	0.049*
H1B	0.4525	0.5535	0.6992	0.049*
C2	0.7218 (4)	0.6084 (3)	0.8905 (3)	0.0479 (8)
H2A	0.7945	0.6057	0.8214	0.072*
H2B	0.7588	0.5762	0.9739	0.072*
H2C	0.6940	0.6866	0.9059	0.072*
C3	0.4831 (3)	0.5398 (2)	0.9448 (3)	0.0464 (8)
H3	0.3984	0.5110	0.8981	0.056*
H3'	0.4654	0.6157	0.9814	0.056*	0.50
C4	0.4443 (7)	0.6608 (5)	1.0048 (6)	0.0403 (13)	0.50
H4A	0.5114	0.6802	1.0760	0.060*	0.50
H4B	0.3489	0.6588	1.0416	0.060*	0.50
H4C	0.4489	0.7172	0.9335	0.060*	0.50
C11	0.6426 (3)	0.5669 (2)	0.6023 (3)	0.0346 (6)
C12	0.6469 (3)	0.6424 (2)	0.4950 (3)	0.0370 (6)
C13	0.7364 (3)	0.6175 (2)	0.3882 (3)	0.0386 (7)
C14	0.8205 (3)	0.5226 (2)	0.3842 (3)	0.0372 (7)
C15	0.8119 (3)	0.4494 (2)	0.4901 (3)	0.0411 (7)
H15	0.8676	0.3832	0.4896	0.049*
C16	0.7241 (3)	0.4695 (2)	0.5979 (3)	0.0371 (6)
C17	0.5559 (4)	0.7462 (3)	0.4936 (4)	0.0539 (9)
H17A	0.6010	0.8052	0.5473	0.081*
H17B	0.4636	0.7284	0.5314	0.081*
H17C	0.5440	0.7725	0.4012	0.081*
C18	0.9182 (3)	0.4993 (3)	0.2693 (3)	0.0506 (8)
H18A	0.9715	0.4305	0.2874	0.076*
H18B	0.9836	0.5624	0.2590	0.076*
H18C	0.8632	0.4900	0.1867	0.076*

	U11	U22	U33	U12	U13	U23
Cl1	0.0693 (6)	0.0651 (6)	0.0429 (5)	0.0039 (4)	0.0184 (4)	0.0072 (4)
N1	0.0397 (13)	0.0333 (12)	0.0421 (14)	−0.0020 (9)	0.0198 (11)	0.0028 (10)
O1	0.0586 (14)	0.0358 (11)	0.0515 (14)	0.0070 (9)	0.0185 (11)	0.0011 (10)
C1	0.0323 (15)	0.0451 (16)	0.0457 (18)	0.0006 (12)	0.0128 (12)	0.0010 (13)
C2	0.0512 (19)	0.0565 (18)	0.0361 (17)	−0.0031 (15)	0.0128 (14)	−0.0041 (14)
C3	0.0454 (18)	0.0442 (16)	0.0499 (19)	0.0062 (13)	0.0217 (14)	0.0130 (14)
C4	0.049 (3)	0.040 (3)	0.032 (3)	0.007 (2)	0.015 (3)	0.008 (2)
C11	0.0263 (13)	0.0379 (14)	0.0396 (16)	−0.0048 (10)	0.0067 (11)	−0.0064 (11)
C12	0.0332 (14)	0.0396 (15)	0.0383 (16)	−0.0025 (11)	0.0055 (12)	−0.0041 (12)
C13	0.0372 (15)	0.0436 (15)	0.0350 (16)	−0.0044 (12)	0.0060 (12)	−0.0047 (12)
C14	0.0300 (14)	0.0469 (16)	0.0348 (15)	−0.0060 (12)	0.0059 (11)	−0.0117 (12)
C15	0.0362 (15)	0.0422 (15)	0.0448 (17)	0.0034 (12)	0.0040 (13)	−0.0134 (13)
C16	0.0359 (15)	0.0342 (14)	0.0413 (16)	−0.0045 (11)	0.0069 (12)	−0.0036 (12)
C17	0.061 (2)	0.0508 (18)	0.050 (2)	0.0165 (15)	0.0152 (16)	0.0071 (15)
C18	0.0440 (17)	0.067 (2)	0.0415 (18)	0.0017 (15)	0.0125 (14)	−0.0143 (15)

Cl1—C13	1.758 (3)	C4—H4B	0.9800
N1—C1	1.464 (4)	C4—H4C	0.9800
N1—C2	1.468 (4)	C11—C16	1.396 (4)
N1—C3	1.483 (4)	C11—C12	1.399 (4)
O1—C16	1.358 (4)	C12—C13	1.400 (4)
O1—H1	0.82 (5)	C12—C17	1.508 (4)
C1—C11	1.514 (4)	C13—C14	1.385 (4)
C1—H1A	0.9900	C14—C15	1.373 (4)
C1—H1B	0.9900	C14—C18	1.506 (4)
C2—H2A	0.9800	C15—C16	1.386 (4)
C2—H2B	0.9800	C15—H15	0.9500
C2—H2C	0.9800	C17—H17A	0.9800
C3—C3i	1.486 (6)	C17—H17B	0.9800
C3—C4	1.604 (6)	C17—H17C	0.9800
C3—H3	0.9886	C18—H18A	0.9800
C3—H3'	0.9905	C18—H18B	0.9800
C4—H3'	0.6186	C18—H18C	0.9800
C4—H4A	0.9800
C1—N1—C2	110.1 (2)	C16—C11—C12	119.5 (3)
C1—N1—C3	109.4 (2)	C16—C11—C1	120.4 (3)
C2—N1—C3	113.9 (2)	C12—C11—C1	120.1 (2)
C16—O1—H1	108 (3)	C11—C12—C13	117.9 (3)
N1—C1—C11	113.1 (2)	C11—C12—C17	121.0 (3)
N1—C1—H1A	108.9	C13—C12—C17	121.1 (3)
C11—C1—H1A	108.9	C14—C13—C12	123.3 (3)
N1—C1—H1B	108.9	C14—C13—Cl1	117.9 (2)
C11—C1—H1B	108.9	C12—C13—Cl1	118.8 (2)
H1A—C1—H1B	107.8	C15—C14—C13	117.3 (3)
N1—C2—H2A	109.5	C15—C14—C18	120.7 (3)
N1—C2—H2B	109.5	C13—C14—C18	122.1 (3)
H2A—C2—H2B	109.5	C14—C15—C16	121.9 (3)
N1—C2—H2C	109.5	C14—C15—H15	119.1
H2A—C2—H2C	109.5	C16—C15—H15	119.1
H2B—C2—H2C	109.5	O1—C16—C15	117.9 (3)
N1—C3—C3i	110.8 (3)	O1—C16—C11	121.9 (3)
N1—C3—C4	113.2 (3)	C15—C16—C11	120.3 (3)
C3i—C3—C4	110.2 (4)	C12—C17—H17A	109.5
N1—C3—H3	107.5	C12—C17—H17B	109.5
C3i—C3—H3	107.5	H17A—C17—H17B	109.5
C4—C3—H3	107.4	C12—C17—H17C	109.5
N1—C3—H3'	110.3	H17A—C17—H17C	109.5
C3i—C3—H3'	110.1	H17B—C17—H17C	109.5
H3—C3—H3'	110.5	C14—C18—H18A	109.5
C3—C4—H4A	109.5	C14—C18—H18B	109.5
C3—C4—H4B	109.5	H18A—C18—H18B	109.5
H4A—C4—H4B	109.5	C14—C18—H18C	109.5
C3—C4—H4C	109.5	H18A—C18—H18C	109.5
H4A—C4—H4C	109.5	H18B—C18—H18C	109.5
H4B—C4—H4C	109.5
C2—N1—C1—C11	69.4 (3)	C11—C12—C13—Cl1	179.3 (2)
C3—N1—C1—C11	−164.7 (2)	C17—C12—C13—Cl1	0.3 (4)
C1—N1—C3—C3i	159.9 (3)	C12—C13—C14—C15	1.2 (4)
C2—N1—C3—C3i	−76.3 (4)	Cl1—C13—C14—C15	−178.2 (2)
C1—N1—C3—C4	−75.7 (4)	C12—C13—C14—C18	−178.6 (3)
C2—N1—C3—C4	48.0 (4)	Cl1—C13—C14—C18	2.0 (4)
N1—C1—C11—C16	33.1 (4)	C13—C14—C15—C16	−0.7 (4)
N1—C1—C11—C12	−149.8 (3)	C18—C14—C15—C16	179.1 (3)
N1—C3—C3i—N1i	−180.0 (2)	C14—C15—C16—O1	178.9 (3)
C16—C11—C12—C13	−1.4 (4)	C14—C15—C16—C11	−0.9 (4)
C1—C11—C12—C13	−178.5 (3)	C12—C11—C16—O1	−177.8 (3)
C16—C11—C12—C17	177.5 (3)	C1—C11—C16—O1	−0.7 (4)
C1—C11—C12—C17	0.4 (4)	C12—C11—C16—C15	2.0 (4)
C11—C12—C13—C14	−0.2 (4)	C1—C11—C16—C15	179.1 (3)
C17—C12—C13—C14	−179.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82 (5)	1.87 (5)	2.614 (3)	150 (4)
C1—H1B···Cg1ii	0.99	2.83	3.709 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82 (5)	1.87 (5)	2.614 (3)	150 (4)
C1—H1B⋯Cg1i	0.99	2.83	3.709 (3)	148

Symmetry code: (i) .