N,N,N′,N′-Tetra­kis(2-hy­droxy-5-methyl­benz­yl)ethane-1,2-diamine dimethyl­formamide disolvate

Wang, N.-S.; Wang, Y.-T.; Guo, X.-K.; Li, T.-D.

doi:10.1107/S1600536811017934

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1438

doi:10.1107/S1600536811017934

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N,N,N′,N′-Tetrakis(2-hydroxy-5-methylbenzyl)ethane-1,2-diamine dimethylformamide disolvate

Nuan-Sheng Wang,^a Yong-Tao Wang,^a Xiu-Kai Guo ^b and Tian-Duo Li ^a ^*

^aShandong Provincial Key Laboratory of Fine Chemicals, Shandong Polytechnic University, Jinan 250353, People's Republic of China, and ^bSchool of Petrochemical Engineering, Changzhou University, Changzhou 213164, People's Republic of China
^*Correspondence e-mail: litianduo@163.com

(Received 8 May 2011; accepted 12 May 2011; online 20 May 2011)

The title compound, C₃₄H₄₀N₂O₄·2C₃H₇NO, was synthesized by the Mannich condensation of ethanediamine, formaldehyde and p-cresol. In the crystal, the tetraphenol molecule is arranged around an inversion center. The molecule and the dimethylformamide solvate are linked through an O—H⋯O hydrogen bond. An intramolecular O—H⋯N hydrogen bond occurs in the tetraphenol molecule, which may influence the molecular confomation. Futhermore, C—H⋯O and π–π stacking interactions [centroid–centroid distance = 3.7081 (14) Å] stabilize the crystal packing, building a three-dimensional network.

Related literature

For applications of the title compound, see: Liu et al. (2007 ); Tshuva et al. (2000 ); For related structures, see: Hou et al. (2010 ); Higham et al. (2006 ); Farrell et al. (2007 ).

Experimental

Crystal data

C₃₄H₄₀N₂O₄·2C₃H₇NO
M_r = 686.87
Monoclinic, P 2₁ /c
a = 11.574 (2) Å
b = 6.3557 (12) Å
c = 26.343 (5) Å
β = 94.939 (3)°
V = 1930.7 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.50 × 0.32 × 0.27 mm

Data collection

Bruker SMART APEX diffractometer
9607 measured reflections
3569 independent reflections
2667 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.154
S = 1.07
3569 reflections
232 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.98	2.705 (2)	147
O2—H2⋯O3	0.82	1.87	2.690 (2)	177
C18—H18⋯O3ⁱ	0.93	2.56	3.368 (3)	145
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017934/dn2686sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017934/dn2686Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017934/dn2686Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536811017934/dn2686Isup4.cml

checkCIF report

Comment top

Multidentate aminophenol are of interest as metallochelators and as ligands for bioinorganic modeling, catalysis, and medical imaging.(Higham et al., 2006; Farrell et al., 2007). Some of them in combination with metals are used as active catalysts for alkenes polymerization (Tshuva et al., 2000) and initiators in the ring-openingpolymerization of lactones (Liu et al., 2007). Herein, we report the crystal structure of the title compound, 'C₃₄H₄₀N₂O₄.(C₃H₇NO)₂'.

The N, N'-Tetrakis(2-hydroxy-5-methylbenzyl)-1, 2-ethanediamine molecule is arranged around inversion center located in the middle of the CH₂-CH₂ bond. The DMF solvate is linked to this molecule through O-H···O hydrogen bonds (Fig. 1). There is also a weak intramolecular O-H···N interactions which might influence the conformation of the molecule (Table 1) (Hou et al., 2010).

The occurence of weak C-H···O interactions (Table 1) and π-π stacking between the symmetry related C1—C6 phenyl rings (Centroid to centroid distance of 3.7081 (14)Å, interplanar distance of 3.6891 (8)° and slippage of 0.375Å) result in the formation of a three dimensional network (Fig. 2)

Related literature top

For applications of the title compound, see: Liu et al. (2007); Tshuva et al. (2000); For related structures, see: Hou et al. (2010); Higham et al. (2006); Farrell et al. (2007).

Experimental top

The title compound was prepared by mixing ethylenediamine (1.0 mmol), paraformaldehyde (4.0 mmol) and p-cresol (10 mmol) were heated to 90°C and stirred for 18 h. This reaction requires no solvent nor inert atmosphere. At the end of the reaction, 10ml of ethanol was added to the mixtures to remove the unreacted p-cresol, then sonicated 10 minutes. Finally a white precipitate product was collected by filtration in 56% yield.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound with the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small sphere of arbitrary radii. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry code: (i) -x+1, -y+1, -z+1]
	Fig. 2. Molecular packing of the title compound viewing along the crystallographic b-axis. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

2-{[(2-{bis[(2-hydroxy-5-methylphenyl)methyl]amino}ethyl)[(2-hydroxy-5- methylphenyl)methyl]amino]methyl}-4-methylphenol dimethylformamide disolvate top

Crystal data top

C₃₄H₄₀N₂O₄·2C₃H₇NO	F(000) = 740
M_r = 686.87	D_x = 1.182 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2283 reflections
a = 11.574 (2) Å	θ = 2.3–22.4°
b = 6.3557 (12) Å	µ = 0.08 mm⁻¹
c = 26.343 (5) Å	T = 298 K
β = 94.939 (3)°	Block, colourless
V = 1930.7 (6) Å³	0.50 × 0.32 × 0.27 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	2667 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 25.5°, θ_min = 1.6°
ϕ and ω scans	h = −13→13
9607 measured reflections	k = 0→7
3569 independent reflections	l = 0→31

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0747P)² + 0.2941P] where P = (F_o² + 2F_c²)/3
3569 reflections	(Δ/σ)_max = 0.003
232 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₃₄H₄₀N₂O₄·2C₃H₇NO	V = 1930.7 (6) Å³
M_r = 686.87	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.574 (2) Å	µ = 0.08 mm⁻¹
b = 6.3557 (12) Å	T = 298 K
c = 26.343 (5) Å	0.50 × 0.32 × 0.27 mm
β = 94.939 (3)°

Data collection top

Bruker SMART APEX diffractometer	2667 reflections with I > 2σ(I)
9607 measured reflections	R_int = 0.029
3569 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.07	Δρ_max = 0.19 e Å⁻³
3569 reflections	Δρ_min = −0.15 e Å⁻³
232 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.81761 (16)	0.6724 (3)	0.50272 (8)	0.0459 (5)
C2	0.80450 (15)	0.4662 (3)	0.48545 (7)	0.0399 (5)
C3	0.86027 (16)	0.4078 (3)	0.44304 (7)	0.0472 (5)
H3	0.8508	0.2709	0.4309	0.057*
C4	0.92929 (17)	0.5440 (4)	0.41797 (8)	0.0546 (6)
C5	0.94148 (18)	0.7469 (4)	0.43666 (9)	0.0602 (6)
H5	0.9880	0.8417	0.4209	0.072*
C6	0.88609 (17)	0.8110 (4)	0.47813 (9)	0.0567 (6)
H6	0.8948	0.9487	0.4897	0.068*
C7	0.9908 (2)	0.4688 (5)	0.37314 (10)	0.0846 (9)
H7A	1.0649	0.4111	0.3851	0.127*
H7B	1.0018	0.5849	0.3508	0.127*
H7C	0.9450	0.3624	0.3551	0.127*
C8	0.74176 (15)	0.3055 (3)	0.51447 (7)	0.0434 (5)
H8A	0.7213	0.1869	0.4923	0.052*
H8B	0.7933	0.2546	0.5428	0.052*
C9	0.59865 (17)	0.2520 (3)	0.57452 (7)	0.0465 (5)
H9A	0.6064	0.1064	0.5642	0.056*
H9B	0.5174	0.2778	0.5787	0.056*
C10	0.66842 (16)	0.2860 (3)	0.62476 (7)	0.0444 (5)
C11	0.74762 (17)	0.1400 (4)	0.64530 (8)	0.0503 (5)
H11	0.7593	0.0176	0.6271	0.060*
C12	0.81018 (19)	0.1691 (4)	0.69194 (8)	0.0571 (6)
C13	0.7899 (2)	0.3509 (5)	0.71814 (8)	0.0648 (7)
H13	0.8299	0.3731	0.7498	0.078*
C14	0.71194 (19)	0.5012 (4)	0.69888 (8)	0.0615 (6)
H14	0.7001	0.6229	0.7174	0.074*
C15	0.65167 (18)	0.4696 (4)	0.65193 (8)	0.0521 (6)
C16	0.8989 (2)	0.0118 (5)	0.71276 (11)	0.0892 (9)
H16A	0.9725	0.0439	0.7004	0.134*
H16B	0.8751	−0.1269	0.7019	0.134*
H16C	0.9057	0.0181	0.7493	0.134*
C17	0.54400 (16)	0.4187 (3)	0.49300 (7)	0.0463 (5)
H17A	0.5051	0.2856	0.4858	0.056*
H17B	0.5782	0.4636	0.4624	0.056*
N1	0.63564 (12)	0.3898 (3)	0.53418 (5)	0.0406 (4)
O1	0.76581 (13)	0.7432 (3)	0.54411 (6)	0.0640 (5)
H1	0.7179	0.6567	0.5520	0.096*
O2	0.57293 (15)	0.6113 (3)	0.63071 (6)	0.0721 (5)
H2	0.5563	0.6957	0.6525	0.108*
C18	0.4736 (2)	1.0737 (4)	0.69918 (8)	0.0546 (6)
H18	0.5089	1.1710	0.7219	0.066*
C19	0.3253 (3)	0.9941 (6)	0.63369 (15)	0.1233 (13)
H19A	0.3785	0.8864	0.6252	0.185*
H19B	0.2982	1.0695	0.6034	0.185*
H19C	0.2606	0.9307	0.6484	0.185*
C20	0.3383 (3)	1.3486 (5)	0.67385 (12)	0.0963 (10)
H20A	0.3860	1.4260	0.6990	0.144*
H20B	0.2604	1.3422	0.6837	0.144*
H20C	0.3385	1.4176	0.6414	0.144*
N2	0.38342 (17)	1.1383 (3)	0.67004 (7)	0.0636 (5)
O3	0.51586 (16)	0.8979 (3)	0.69941 (6)	0.0731 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0384 (10)	0.0481 (13)	0.0502 (12)	0.0064 (9)	−0.0022 (9)	−0.0022 (10)
C2	0.0319 (9)	0.0477 (12)	0.0389 (10)	0.0071 (8)	−0.0024 (8)	0.0010 (9)
C3	0.0417 (11)	0.0552 (13)	0.0442 (11)	0.0071 (9)	0.0001 (9)	−0.0009 (10)
C4	0.0419 (11)	0.0752 (17)	0.0469 (12)	0.0068 (11)	0.0041 (9)	0.0115 (11)
C5	0.0422 (12)	0.0656 (17)	0.0723 (15)	−0.0005 (11)	0.0026 (11)	0.0213 (13)
C6	0.0442 (12)	0.0465 (13)	0.0783 (16)	0.0004 (10)	−0.0007 (11)	0.0036 (11)
C7	0.0739 (17)	0.120 (3)	0.0630 (15)	−0.0014 (17)	0.0253 (14)	0.0050 (16)
C8	0.0400 (10)	0.0458 (12)	0.0440 (11)	0.0088 (9)	0.0025 (8)	−0.0009 (9)
C9	0.0428 (11)	0.0514 (13)	0.0455 (11)	−0.0021 (9)	0.0049 (9)	−0.0026 (9)
C10	0.0452 (11)	0.0516 (13)	0.0377 (10)	−0.0029 (9)	0.0106 (8)	0.0003 (9)
C11	0.0540 (12)	0.0500 (13)	0.0477 (11)	−0.0015 (10)	0.0098 (10)	0.0024 (10)
C12	0.0546 (13)	0.0705 (16)	0.0458 (12)	−0.0007 (11)	0.0019 (10)	0.0075 (11)
C13	0.0586 (14)	0.093 (2)	0.0422 (12)	−0.0093 (13)	−0.0011 (11)	−0.0027 (13)
C14	0.0633 (14)	0.0755 (17)	0.0469 (12)	−0.0021 (12)	0.0109 (11)	−0.0160 (11)
C15	0.0515 (12)	0.0600 (15)	0.0458 (12)	0.0057 (10)	0.0107 (10)	−0.0030 (10)
C16	0.0865 (19)	0.100 (2)	0.0772 (18)	0.0155 (17)	−0.0128 (16)	0.0156 (16)
C17	0.0416 (10)	0.0563 (13)	0.0402 (10)	0.0066 (9)	−0.0011 (8)	−0.0110 (9)
N1	0.0364 (8)	0.0495 (10)	0.0361 (8)	0.0050 (7)	0.0033 (7)	−0.0033 (7)
O1	0.0680 (11)	0.0568 (11)	0.0690 (10)	−0.0011 (8)	0.0163 (8)	−0.0191 (8)
O2	0.0804 (12)	0.0741 (13)	0.0611 (10)	0.0264 (9)	0.0021 (9)	−0.0153 (9)
C18	0.0682 (14)	0.0544 (15)	0.0419 (11)	0.0012 (12)	0.0088 (11)	−0.0042 (10)
C19	0.123 (3)	0.123 (3)	0.114 (3)	−0.020 (2)	−0.048 (2)	−0.016 (2)
C20	0.096 (2)	0.089 (2)	0.103 (2)	0.0314 (18)	0.0033 (18)	0.0172 (18)
N2	0.0689 (12)	0.0650 (14)	0.0549 (11)	−0.0008 (10)	−0.0066 (10)	0.0031 (10)
O3	0.0999 (13)	0.0595 (11)	0.0612 (10)	0.0219 (10)	0.0149 (9)	−0.0026 (8)

Geometric parameters (Å, º) top

C1—O1	1.365 (2)	C12—C16	1.502 (4)
C1—C6	1.383 (3)	C13—C14	1.380 (3)
C1—C2	1.391 (3)	C13—H13	0.9300
C2—C3	1.388 (3)	C14—C15	1.381 (3)
C2—C8	1.500 (3)	C14—H14	0.9300
C3—C4	1.384 (3)	C15—O2	1.366 (3)
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.383 (3)	C16—H16B	0.9600
C4—C7	1.508 (3)	C16—H16C	0.9600
C5—C6	1.375 (3)	C17—N1	1.462 (2)
C5—H5	0.9300	C17—C17ⁱ	1.518 (4)
C6—H6	0.9300	C17—H17A	0.9700
C7—H7A	0.9600	C17—H17B	0.9700
C7—H7B	0.9600	O1—H1	0.8200
C7—H7C	0.9600	O2—H2	0.8200
C8—N1	1.475 (2)	C18—O3	1.219 (3)
C8—H8A	0.9700	C18—N2	1.307 (3)
C8—H8B	0.9700	C18—H18	0.9300
C9—N1	1.469 (2)	C19—N2	1.449 (4)
C9—C10	1.506 (3)	C19—H19A	0.9600
C9—H9A	0.9700	C19—H19B	0.9600
C9—H9B	0.9700	C19—H19C	0.9600
C10—C11	1.381 (3)	C20—N2	1.442 (3)
C10—C15	1.391 (3)	C20—H20A	0.9600
C11—C12	1.384 (3)	C20—H20B	0.9600
C11—H11	0.9300	C20—H20C	0.9600
C12—C13	1.376 (4)

O1—C1—C6	118.2 (2)	C12—C13—C14	122.1 (2)
O1—C1—C2	121.92 (18)	C12—C13—H13	119.0
C6—C1—C2	119.9 (2)	C14—C13—H13	119.0
C3—C2—C1	118.04 (19)	C13—C14—C15	119.5 (2)
C3—C2—C8	120.45 (18)	C13—C14—H14	120.3
C1—C2—C8	121.25 (17)	C15—C14—H14	120.3
C4—C3—C2	123.0 (2)	O2—C15—C14	122.6 (2)
C4—C3—H3	118.5	O2—C15—C10	117.40 (18)
C2—C3—H3	118.5	C14—C15—C10	120.0 (2)
C5—C4—C3	117.3 (2)	C12—C16—H16A	109.5
C5—C4—C7	122.3 (2)	C12—C16—H16B	109.5
C3—C4—C7	120.4 (2)	H16A—C16—H16B	109.5
C6—C5—C4	121.3 (2)	C12—C16—H16C	109.5
C6—C5—H5	119.4	H16A—C16—H16C	109.5
C4—C5—H5	119.4	H16B—C16—H16C	109.5
C5—C6—C1	120.6 (2)	N1—C17—C17ⁱ	111.36 (19)
C5—C6—H6	119.7	N1—C17—H17A	109.4
C1—C6—H6	119.7	C17ⁱ—C17—H17A	109.4
C4—C7—H7A	109.5	N1—C17—H17B	109.4
C4—C7—H7B	109.5	C17ⁱ—C17—H17B	109.4
H7A—C7—H7B	109.5	H17A—C17—H17B	108.0
C4—C7—H7C	109.5	C17—N1—C9	111.94 (15)
H7A—C7—H7C	109.5	C17—N1—C8	110.94 (14)
H7B—C7—H7C	109.5	C9—N1—C8	109.95 (15)
N1—C8—C2	112.72 (16)	C1—O1—H1	109.5
N1—C8—H8A	109.0	C15—O2—H2	109.5
C2—C8—H8A	109.0	O3—C18—N2	126.2 (2)
N1—C8—H8B	109.0	O3—C18—H18	116.9
C2—C8—H8B	109.0	N2—C18—H18	116.9
H8A—C8—H8B	107.8	N2—C19—H19A	109.5
N1—C9—C10	112.49 (16)	N2—C19—H19B	109.5
N1—C9—H9A	109.1	H19A—C19—H19B	109.5
C10—C9—H9A	109.1	N2—C19—H19C	109.5
N1—C9—H9B	109.1	H19A—C19—H19C	109.5
C10—C9—H9B	109.1	H19B—C19—H19C	109.5
H9A—C9—H9B	107.8	N2—C20—H20A	109.5
C11—C10—C15	118.63 (19)	N2—C20—H20B	109.5
C11—C10—C9	122.36 (19)	H20A—C20—H20B	109.5
C15—C10—C9	119.00 (18)	N2—C20—H20C	109.5
C10—C11—C12	122.5 (2)	H20A—C20—H20C	109.5
C10—C11—H11	118.8	H20B—C20—H20C	109.5
C12—C11—H11	118.8	C18—N2—C20	121.7 (2)
C13—C12—C11	117.3 (2)	C18—N2—C19	119.4 (3)
C13—C12—C16	121.1 (2)	C20—N2—C19	118.8 (3)
C11—C12—C16	121.6 (2)

O1—C1—C2—C3	179.97 (17)	C10—C11—C12—C13	0.7 (3)
C6—C1—C2—C3	−0.9 (3)	C10—C11—C12—C16	−177.9 (2)
O1—C1—C2—C8	−5.9 (3)	C11—C12—C13—C14	−1.0 (3)
C6—C1—C2—C8	173.23 (18)	C16—C12—C13—C14	177.5 (2)
C1—C2—C3—C4	1.1 (3)	C12—C13—C14—C15	0.2 (4)
C8—C2—C3—C4	−173.15 (18)	C13—C14—C15—O2	179.7 (2)
C2—C3—C4—C5	−0.2 (3)	C13—C14—C15—C10	0.9 (3)
C2—C3—C4—C7	177.9 (2)	C11—C10—C15—O2	179.93 (18)
C3—C4—C5—C6	−0.7 (3)	C9—C10—C15—O2	−0.9 (3)
C7—C4—C5—C6	−178.9 (2)	C11—C10—C15—C14	−1.2 (3)
C4—C5—C6—C1	0.9 (3)	C9—C10—C15—C14	177.91 (19)
O1—C1—C6—C5	179.13 (19)	C17ⁱ—C17—N1—C9	80.0 (3)
C2—C1—C6—C5	0.0 (3)	C17ⁱ—C17—N1—C8	−156.7 (2)
C3—C2—C8—N1	−144.07 (17)	C10—C9—N1—C17	−157.41 (16)
C1—C2—C8—N1	41.9 (2)	C10—C9—N1—C8	78.8 (2)
N1—C9—C10—C11	−109.0 (2)	C2—C8—N1—C17	73.2 (2)
N1—C9—C10—C15	71.9 (2)	C2—C8—N1—C9	−162.47 (15)
C15—C10—C11—C12	0.4 (3)	O3—C18—N2—C20	178.2 (2)
C9—C10—C11—C12	−178.70 (19)	O3—C18—N2—C19	−0.4 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.98	2.705 (2)	147
O2—H2···O3	0.82	1.87	2.690 (2)	177
C18—H18···O3ⁱⁱ	0.93	2.56	3.368 (3)	145

Symmetry code: (ii) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₃₄H₄₀N₂O₄·2C₃H₇NO
M_r	686.87
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.574 (2), 6.3557 (12), 26.343 (5)
β (°)	94.939 (3)
V (Å³)	1930.7 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.32 × 0.27

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9607, 3569, 2667
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.154, 1.07
No. of reflections	3569
No. of parameters	232
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.15

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), SHELXTL (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	1.98	2.705 (2)	147
O2—H2···O3	0.82	1.87	2.690 (2)	177
C18—H18···O3ⁱ	0.93	2.56	3.368 (3)	145

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Acknowledgements

We thank the Shandong Province Higher Educational Science and Technology Program for financial support (J09LB03).

References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Farrell, J. R., Niconchuk, J., Higham, C. S. & Bergeron, B. W. (2007). Tetrahedron Lett. 48, 8034–8036. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Higham, C. S., Dowling, D. P., Shaw, J. L. & Farrell, J. R. (2006). Tetrahedron Lett. 47, 4419–4423 CrossRef CAS Google Scholar
Hou, G.-G., Ma, J.-P., Wang, L., Wang, P., Dong, Y.-B. & Huang, R.-Q. (2010). CrystEngComm, 12, 4287–4303. Web of Science CSD CrossRef CAS Google Scholar
Liu, X. L., Shang, X. M., Tang, T. & Cui, D. M. (2007). Organometallics, 26, 2747–2757. CrossRef Google Scholar
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Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 67| Part 6| June 2011| Page o1438

doi:10.1107/S1600536811017934

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

N,N,N′,N′-Tetra­kis(2-hy­dr­oxy-5-methyl­benz­yl)ethane-1,2-di­amine di­methyl­formamide disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N,N,N′,N′-Tetrakis(2-hydroxy-5-methylbenzyl)ethane-1,2-diamine dimethylformamide disolvate