rac-4-Chloro-2-[({2-[(3-chloro-6-hy­droxy-2,4-dimethyl­benz­yl)(meth­yl)amino]­prop­yl}(meth­yl)amino)­meth­yl]-3,5-dimethyl­phenol

Rivera, A.; Pacheco, D.J.; Ríos-Motta, J.; Maldonado, M.; Bolte, M.

doi:10.1107/S1600536812039694

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2997

https://doi.org/10.1107/S1600536812039694

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rac-4-Chloro-2-[({2-[(3-chloro-6-hydroxy-2,4-dimethylbenzyl)(methyl)amino]propyl}(methyl)amino)methyl]-3,5-dimethylphenol

Augusto Rivera,^a ^* Dency José Pacheco,^a Jaime Ríos-Motta,^a Mauricio Maldonado ^a and Michael Bolte ^b

^aDepartamento de Química, Facultad de Ciencias, Universidad Nacional de Colombia, Sede Bogotá, Cra 30 No. 45-03, Bogotá, Código Postal 111321, Colombia, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: ariverau@unal.edu.co

(Received 7 September 2012; accepted 18 September 2012; online 26 September 2012)

The title compound, C₂₃H₃₂Cl₂N₂O₂, a potential chiral ligand for coordination chemistry, was prepared by a two-step reaction. The molecule is located on a crystallographic centre of inversion. As a result, the methyl group bonded to the methylene 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-diaminopropane unit adopts an antiperiplanar conformation and the two benzene rings are coplanar. The central chain is in an all-trans arrangement. An intramolecular O—H⋯N hydrogen bond makes an S(6) ring motif. A C—H⋯π interaction links the molecules 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_r = 439.41
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.064
wR(F²) = 0.159
S = 1.14
2055 reflections
144 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.35 e Å⁻³

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) -x+1, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812039694/go2069sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039694/go2069Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812039694/go2069Isup3.cml

checkCIF report

Comment top

Compound I, C₂₃H₃₂Cl₂N₂O₂, a new chiral N,N-dimethylated tetrahydrosalen (H2[H4]salen) was obtained by reacting the bis-benzoxazine (II) with sodium borohydride using our procedure reported earlier (Rivera et al. 2010). The intermediate II was prepared by condensing 1,2-diaminepropane with formaldehyde and 4-chloro-3,5-dimethylphenol employing the general procedure of Burke (1949). The synthetic route for the title compound reported herein is illustrated in Fig. 1. The molecular structure and atom-numbering scheme for title compound, C₂₃H₃₂Cl₂N₂O₂, are shown in Fig. 2. The bond/newcifs lengths (Allen et al., 1987) and angles are normal and similar to those observed for related structures (Rivera et al. 2010; Xu et al. 2009). In the title molecule, the 1,2-propanodiamine unit adopts an antiperiplanar conformation with an N1—C3—C3a—N1a torsion angle of -180.0 (2)°. As a consequence of this conformation, both benzene rings are parallel to each other. The central chain –CH₂—N(CH₃)—CH₂—CH(CH₃)—N(CH₃)—CH₂– is found in an all-trans arrangement. The two symmetry-related methyl substituents in the molecule (C2 and C2ⁱ, (i) = 1 - x, 1 - y, 2 - z) are orientated in an antiperiplanar arrangement (pseudo torsion angle CH₃—N···N—CH₃ = 180.00°). The C2 and C4 methyl groups are almost (+)-synclinal [C2—N1—C3—C4 torsion angle = 48.0 (4)°], a conformation stabilized by an intramolecular O—H···N hydrogen bond. The relationship of C4 methyl to C2ⁱ is defined by the pseudo torsion angle C4—C3···N1a—C2a, which is 114.64 (3)°.

The intramolecular O—H···N hydrogen bond (Table 1) makes an S(6) ring motif (Bernstein et al., 1995), contrasting with the related structure (Xu et al., 2009). In the crystal structure, intermolecular C1—H1B···Cg1(1 - x, 1 - y, 1 - z) interaction links the molecules into one-dimensional chains. C1···Cg1 is 3.709 (3)Å, H1···Cg1 is 2.83Å and the angle at H1 is 148°. Cg1 is the centroid of the C11–C16 ring.

Related literature top

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 a related structure, 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 top

Sodium borohydride (3.0 mmol, 0.11 g) was added to a solution of 3,3'-(propane-1,2-diyl)bis(6-chloro-5,7-dimethyl-3,4-dihydro-2 h-benzo[e][1,3]oxazina) (435 mg, 1 mmol) (II) in ethanol (15 ml), and the mixture was stirred magnetically for 30 min at room temperature. After completion of the reaction, the mixture was poured into ice-cold water, neutralized with ammonium chloride (12 ml), and extracted with CHCl₃ (3 × 10 ml). The combined extracts were dried over anhydrous Na₂SO₄ and evaporated. Recrystallization from ethanol afforded (I) in 91% yield. m.p. 424 K.

Structure description top

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Synthetic route for the title compound.
	Fig. 2. A perspective view of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Only one of the two positions of the disordered methyl group is shown. Hydrogen bonds are drawn as dashed lines.

rac-4-Chloro-2-[({2-[(3-chloro-6-hydroxy-2,4-dimethylbenzyl)(methyl)amino]propyl}(methyl)amino)methyl]-3,5-dimethylphenol top

Crystal data top

C₂₃H₃₂Cl₂N₂O₂	F(000) = 468
M_r = 439.41	D_x = 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

Data collection top

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	R_int = 0.074
ω scans	θ_max = 25.3°, θ_min = 3.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −11→11
T_min = 0.927, T_max = 0.976	k = −14→14
11151 measured reflections	l = −11→11

Refinement top

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(F_o²) + (0.0629P)² + 0.952P] where P = (F_o² + 2F_c²)/3
2055 reflections	(Δ/σ)_max < 0.001
144 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₃H₃₂Cl₂N₂O₂	V = 1129.19 (19) Å³
M_r = 439.41	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.5011 (8) Å	µ = 0.31 mm⁻¹
b = 11.9060 (13) Å	T = 173 K
c = 9.9824 (9) Å	0.25 × 0.22 × 0.08 mm
β = 90.348 (7)°

Data collection top

Stoe IPDS II two-circle diffractometer	2055 independent reflections
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	1758 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.976	R_int = 0.074
11151 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.59 e Å⁻³
2055 reflections	Δρ_min = −0.35 e Å⁻³
144 parameters

Special details top

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 (CH₃ asym, st), 2922 (CH₂ asym, st), 2855 (CH₃ sym, st), 2802 (CH₂ sym, 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₃₂Cl₂N₂O₂
M_r	439.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	9.5011 (8), 11.9060 (13), 9.9824 (9)
β (°)	90.348 (7)
V (Å³)	1129.19 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.25 × 0.22 × 0.08

Data collection
Diffractometer	Stoe IPDS II two-circle
Absorption correction	Multi-scan (X-AREA; Stoe & Cie, 2001)
T_min, T_max	0.927, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	11151, 2055, 1758
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.159, 1.14
No. of reflections	2055
No. of parameters	144
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.35

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Acknowledgements

The authors acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia, for financial support of this work.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
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Burke, W. J. (1949). J. Am. Chem. Soc. 71, 609–612. CrossRef CAS Web of Science Google Scholar
Rivera, A., Rojas, J. J., Ríos-Motta, J., Dušek, M. & Fejfarová, K. (2011). Acta Cryst. E67, o1391. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rivera, A., Rojas, J. J., Salazar-Barrios, J., Maldonado, M. & Ríos-Motta, J. (2010). Molecules, 15, 4102–4110. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
Xu, Y.-M., Gao, S. & Ng, S. W. (2009). Acta Cryst. E65, o3151. Web of Science CSD CrossRef IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

rac-4-Chloro-2-[({2-[(3-chloro-6-hy­dr­oxy-2,4-di­methyl­benz­yl)(meth­yl)amino]­prop­yl}(meth­yl)amino)­meth­yl]-3,5-di­methyl­phenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-4-Chloro-2-[({2-[(3-chloro-6-hydroxy-2,4-dimethylbenzyl)(methyl)amino]propyl}(methyl)amino)methyl]-3,5-dimethylphenol