N,N,N',N'-Tetra-kis(2-hy-droxy-5-methyl-benz-yl)ethane-1,2-diamine dimethyl-formamide disolvate.

The title compound, C(34)H(40)N(2)O(4)·2C(3)H(7)NO, was synthesized by the Mannich condensation of ethane-diamine, formaldehyde and p-cresol. In the crystal, the tetra-phenol mol-ecule is arranged around an inversion center. The mol-ecule and the dimethyl-formamide solvate are linked through an O-H⋯O hydrogen bond. An intra-molecular O-H⋯N hydrogen bond occurs in the tetra-phenol mol-ecule, which may influence the mol-ecular confomation. Futhermore, C-H⋯O and π-π stacking inter-actions [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 = 686.87

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.154

S = 1.07

3569 reflections

232 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.15 e Å−3

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 ▶).

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

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

Supplementary material file. DOI: 10.1107/S1600536811017934/dn2686Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811017934/dn2686Isup4.cml

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

C34H40N2O4·2C3H7NO	F(000) = 740
Mr = 686.87	Dx = 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

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

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(Fo2) + (0.0747P)2 + 0.2941P] where P = (Fo2 + 2Fc2)/3
3569 reflections	(Δ/σ)max = 0.003
232 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .