A four-armed Schiff base: 6,6′,6′′,6′′′-tetra­meth­oxy-2,2′,2′′,2′′′-[methanetetra­yltetra­kis(methylenenitrilo­methyl­idyne)]tetra­phenol

Jiang, G.-Q.; Cai, J.; Zhang, Y.-Q.; Zhang, Q.-J.

doi:10.1107/S1600536808020618

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1455

doi:10.1107/S1600536808020618

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A four-armed Schiff base: 6,6′,6′′,6′′′-tetramethoxy-2,2′,2′′,2′′′-[methanetetrayltetrakis(methylenenitrilomethylidyne)]tetraphenol

Guang-Qi Jiang,^a ^* Jie Cai,^a Yun-Qian Zhang ^a and Qian-Jun Zhang ^a

^aDepartment of Chemistry, Guizhou University, Guiyang 550025, People's Republic of China
^*Correspondence e-mail: gqjiang@163.com

(Received 23 June 2008; accepted 4 July 2008; online 12 July 2008)

In the structure of the title compound, C₃₇H₄₀N₄O₈, pentaerythrityltetramine is bonded to four o-vanillin molecules, forming a four-armed Schiff base molecule. These molecules are connected by intermolecular C—H⋯O hydrogen bonds. Intramolecular C—H⋯N and O—H⋯N hydrogen bonds are also present.

Related literature

For related literature, see: Tanaka et al. (2006 ); Bernardo et al. (1996 ); Laliberte et al. (2004 ).

Experimental

Crystal data

C₃₇H₄₀N₄O₈
M_r = 668.73
Triclinic, $[P \overline 1]$
a = 11.3464 (11) Å
b = 12.4437 (12) Å
c = 13.0523 (14) Å
α = 75.861 (7)°
β = 88.893 (7)°
γ = 78.385 (7)°
V = 1749.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 273 (2) K
0.18 × 0.16 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.984, T_max = 0.987
16510 measured reflections
6221 independent reflections
3077 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.145
S = 0.94
6194 reflections
443 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.87	2.592 (3)	147
O4—H4⋯N4	0.82	1.84	2.567 (2)	147
O6—H6⋯N3	0.82	1.89	2.623 (3)	148
O7—H7⋯N2	0.82	1.88	2.612 (3)	148
C27—H27B⋯N1	0.97	2.56	2.936 (3)	103
C26—H26⋯O5ⁱ	0.93	2.58	3.309 (3)	136
C28—H28C⋯O2ⁱ	0.96	2.57	3.387 (3)	143
C12—H12⋯O6ⁱⁱ	0.93	2.59	3.400 (3)	146
C32—H32⋯O3ⁱⁱⁱ	0.93	2.42	3.289 (3)	155
C36—H36B⋯O8^iv	0.97	2.55	3.399 (3)	146
Symmetry codes: (i) -x, -y+2, -z; (ii) -x-1, -y+2, -z; (iii) x+1, y, z; (iv) -x, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020618/om2247sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020618/om2247Isup2.hkl

checkCIF report

Comment top

Schiff bases have been intensively investigated during the past decades, mainly because of their strong coordination capability and diverse biological activities, such as antibacterial, antitumor activities, etc. (Tanaka et al., 2006; Bernardo et al., 1996). Pentaerythrityl tetramine and its congeners act as versatile building blocks in supramolecular chemistry and have been widely employed for the synthesis of various spiro crown ethers, spiro-macrocyclic ligands etc. (Laliberte et al., 2004). However, to the best of our knowledge, few Schiff bases and their complexes derived from pentaerythrityl tetramine have been reported. Herein,we present the synthesis and crystal structure of the multidentate Schiff base ligand derived from o-vanillin and pentaerythrityl tetramine.

The molecular structure is shown in Fig.1. The atoms C9, C18, C27, and C36 form a distorted tetrahedral geometry about the central atom C37. The structure reveals four intramolecular O—H···N hydrogen bonds and one C—H···N hydrogen bond as well as five intermolecular C—H···O hydrogen bonds (Table 1). A view of the packing is given in Fig. 2. The molecules are also connected by C—H···π interactions, with C9—H9B···Cg(1) angle of 138 °, C9···Cg(1) distance of 3.595 (3) Å and C14—H14···Cg(4) angle of 157 °, C14···Cg(4) distance of 3.614 (3) Å, where Cg(1) and Cg(4) are the centroids of the phenyl ring formed by atoms C2,C3,C4,C5,C6,C7 and C29,C30,C31,C32,C33,C34 at (1 - x,-y,1 - z) and (1 + x,y,z), respectively.

Related literature top

For related literature, see: Tanaka et al. (2006); Bernardo et al. (1996); Laliberte et al. (2004).

Experimental top

A solution of pentaerythrityl tetramine (0.13 g, 1 mmol) in ethanol (20 ml) was added dropwise while stirring to a solution of o-vanillin (0.68 g, 4 mmol) in ethanol (20 ml),the mixture was stirred for about 2 h at room temperature. The resulting solution was filtered, and after slow evaporation of the solvent for several days, crystals suitable for X-ray diffraction were obtained in a yield of 46.4%.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure shown with 50% probability displacement ellipsoids.
	Fig. 2. One-dimensional chains of the Schiff base perpendicular to the bc plane, showing the packing of the compound. Hydrogen bonds and C—H···π interactions are shown as dashed lines. H atoms have been omitted for clarity.

6,6',6'',6'''-tetramethoxy-2,2',2'',2'''- [methanetetrayltetrakis(methylenenitrilomethylidyne)]tetraphenol top

Crystal data top

C₃₇H₄₀N₄O₈	Z = 2
M_r = 668.73	F(000) = 708
Triclinic, P1	D_x = 1.269 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.3464 (11) Å	Cell parameters from 16510 reflections
b = 12.4437 (12) Å	θ = 1.0–25.1°
c = 13.0523 (14) Å	µ = 0.09 mm⁻¹
α = 75.861 (7)°	T = 273 K
β = 88.893 (7)°	Prism, yellow
γ = 78.385 (7)°	0.18 × 0.16 × 0.15 mm
V = 1749.6 (3) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	6221 independent reflections
Radiation source: fine-focus sealed tube	3077 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −13→13
T_min = 0.984, T_max = 0.987	k = −14→14
16510 measured reflections	l = −13→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.145	w = 1/[σ²(F_o²) + (0.0583P)²] where P = (F_o² + 2F_c²)/3
S = 0.94	(Δ/σ)_max < 0.001
6194 reflections	Δρ_max = 0.18 e Å⁻³
443 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0093 (14)

Crystal data top

C₃₇H₄₀N₄O₈	γ = 78.385 (7)°
M_r = 668.73	V = 1749.6 (3) Å³
Triclinic, P1	Z = 2
a = 11.3464 (11) Å	Mo Kα radiation
b = 12.4437 (12) Å	µ = 0.09 mm⁻¹
c = 13.0523 (14) Å	T = 273 K
α = 75.861 (7)°	0.18 × 0.16 × 0.15 mm
β = 88.893 (7)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	6221 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3077 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.987	R_int = 0.058
16510 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 0.94	Δρ_max = 0.18 e Å⁻³
6194 reflections	Δρ_min = −0.19 e Å⁻³
443 parameters

Special details top

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
C1	−0.6783 (3)	0.6040 (3)	0.6346 (3)	0.1205 (14)
H1A	−0.7350	0.5856	0.5914	0.181*
H1B	−0.7208	0.6457	0.6816	0.181*
H1C	−0.6285	0.5355	0.6752	0.181*
C2	−0.5190 (3)	0.7057 (2)	0.6164 (2)	0.0661 (8)
C3	−0.4819 (3)	0.6681 (2)	0.7207 (2)	0.0689 (8)
H3	−0.5142	0.6112	0.7650	0.083*
C4	−0.3970 (3)	0.7138 (2)	0.7606 (2)	0.0705 (8)
H4A	−0.3729	0.6879	0.8315	0.085*
C5	−0.3483 (2)	0.7971 (2)	0.6962 (2)	0.0637 (7)
H5	−0.2922	0.8283	0.7239	0.076*
C6	−0.3823 (2)	0.8355 (2)	0.5891 (2)	0.0504 (6)
C7	−0.4681 (2)	0.7891 (2)	0.5489 (2)	0.0561 (7)
C8	−0.3299 (2)	0.9225 (2)	0.5203 (2)	0.0556 (7)
H8	−0.2759	0.9550	0.5492	0.067*
C9	−0.2957 (2)	1.0390 (2)	0.35387 (19)	0.0541 (7)
H9A	−0.2517	1.0717	0.3972	0.065*
H9B	−0.3559	1.0994	0.3116	0.065*
C10	−0.7806 (3)	1.3762 (3)	−0.1285 (3)	0.1135 (13)
H10A	−0.7593	1.4442	−0.1701	0.170*
H10B	−0.8450	1.3953	−0.0832	0.170*
H10C	−0.8063	1.3352	−0.1746	0.170*
C11	−0.6932 (2)	1.2070 (2)	−0.0018 (2)	0.0585 (7)
C12	−0.7994 (2)	1.1700 (3)	0.0167 (2)	0.0672 (8)
H12	−0.8709	1.2161	−0.0145	0.081*
C13	−0.8005 (3)	1.0645 (3)	0.0816 (3)	0.0773 (9)
H13	−0.8725	1.0393	0.0929	0.093*
C14	−0.6962 (2)	0.9971 (2)	0.1292 (2)	0.0680 (8)
H14	−0.6979	0.9259	0.1725	0.082*
C15	−0.5875 (2)	1.0334 (2)	0.11382 (19)	0.0511 (7)
C16	−0.5865 (2)	1.1396 (2)	0.0472 (2)	0.0527 (7)
C17	−0.4787 (2)	0.9634 (2)	0.16885 (19)	0.0567 (7)
H17	−0.4822	0.8927	0.2121	0.068*
C18	−0.2728 (2)	0.9217 (2)	0.21916 (19)	0.0540 (7)
H18A	−0.2174	0.8917	0.1707	0.065*
H18B	−0.2971	0.8584	0.2683	0.065*
C19	0.1639 (4)	1.4133 (3)	0.5082 (3)	0.1264 (14)
H19A	0.1696	1.3906	0.5840	0.190*
H19B	0.1277	1.4923	0.4858	0.190*
H19C	0.2429	1.4004	0.4803	0.190*
C20	0.0741 (2)	1.3692 (2)	0.3635 (2)	0.0667 (8)
C21	0.1075 (3)	1.4562 (2)	0.2895 (3)	0.0770 (9)
H21	0.1441	1.5075	0.3116	0.092*
C22	0.0876 (3)	1.4686 (2)	0.1828 (3)	0.0822 (9)
H22	0.1117	1.5272	0.1334	0.099*
C23	0.0320 (2)	1.3938 (2)	0.1502 (2)	0.0727 (8)
H23	0.0183	1.4023	0.0784	0.087*
C24	−0.0044 (2)	1.3052 (2)	0.2232 (2)	0.0509 (7)
C25	0.0163 (2)	1.2936 (2)	0.3301 (2)	0.0581 (7)
C26	−0.0634 (2)	1.2277 (2)	0.1863 (2)	0.0547 (7)
H26	−0.0732	1.2373	0.1138	0.066*
C27	−0.1624 (2)	1.0776 (2)	0.19919 (19)	0.0591 (7)
H27A	−0.1064	1.0425	0.1541	0.071*
H27B	−0.2297	1.1260	0.1550	0.071*
C28	0.3376 (3)	0.6069 (3)	−0.0230 (2)	0.0883 (10)
H28A	0.3091	0.6053	−0.0912	0.132*
H28B	0.3572	0.5312	0.0209	0.132*
H28C	0.4082	0.6394	−0.0308	0.132*
C29	0.2713 (2)	0.6854 (2)	0.1230 (2)	0.0519 (7)
C30	0.3835 (2)	0.6521 (2)	0.1727 (2)	0.0666 (8)
H30	0.4489	0.6186	0.1394	0.080*
C31	0.3984 (3)	0.6687 (3)	0.2720 (3)	0.0782 (9)
H31	0.4743	0.6462	0.3052	0.094*
C32	0.3036 (2)	0.7176 (2)	0.3220 (2)	0.0675 (8)
H32	0.3149	0.7272	0.3894	0.081*
C33	0.1896 (2)	0.7534 (2)	0.27244 (19)	0.0493 (6)
C34	0.1742 (2)	0.7371 (2)	0.1721 (2)	0.0472 (6)
C35	0.0911 (2)	0.8099 (2)	0.3253 (2)	0.0543 (7)
H35	0.1062	0.8195	0.3919	0.065*
C36	−0.1053 (2)	0.9013 (2)	0.3478 (2)	0.0583 (7)
H36A	−0.0667	0.9410	0.3885	0.070*
H36B	−0.1378	0.8435	0.3973	0.070*
C37	−0.2085 (2)	0.9849 (2)	0.28059 (18)	0.0475 (6)
N1	−0.37817 (18)	0.99528 (17)	0.16006 (15)	0.0527 (5)
N2	−0.10224 (18)	1.14746 (18)	0.24823 (16)	0.0586 (6)
N3	−0.01463 (19)	0.84665 (17)	0.28493 (15)	0.0544 (6)
N4	−0.35536 (17)	0.95591 (17)	0.42188 (17)	0.0542 (6)
O1	−0.68132 (17)	1.30936 (18)	−0.06743 (17)	0.0877 (6)
O2	−0.48359 (14)	1.17979 (14)	0.02791 (14)	0.0690 (5)
H2	−0.4272	1.1331	0.0611	0.104*
O3	−0.6060 (2)	0.6698 (2)	0.56997 (16)	0.1045 (8)
O4	−0.50509 (17)	0.82276 (16)	0.44657 (14)	0.0791 (6)
H4	−0.4688	0.8710	0.4150	0.119*
O5	0.24695 (16)	0.67307 (15)	0.02443 (14)	0.0692 (5)
O6	0.06588 (14)	0.77182 (15)	0.12026 (13)	0.0641 (5)
H6	0.0164	0.8014	0.1570	0.096*
O7	−0.01615 (18)	1.20882 (16)	0.40428 (14)	0.0870 (7)
H7	−0.0487	1.1704	0.3754	0.131*
O8	0.0914 (2)	1.34865 (17)	0.47009 (17)	0.1004 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.130 (3)	0.122 (3)	0.118 (3)	−0.077 (3)	0.002 (3)	−0.005 (3)
C2	0.080 (2)	0.0671 (19)	0.0570 (19)	−0.0297 (17)	0.0043 (16)	−0.0143 (16)
C3	0.091 (2)	0.0606 (19)	0.0545 (19)	−0.0213 (17)	0.0114 (17)	−0.0093 (16)
C4	0.087 (2)	0.071 (2)	0.0492 (17)	−0.0113 (17)	0.0006 (16)	−0.0090 (16)
C5	0.0650 (18)	0.076 (2)	0.0539 (18)	−0.0153 (16)	−0.0037 (14)	−0.0208 (16)
C6	0.0527 (15)	0.0560 (16)	0.0465 (16)	−0.0115 (13)	0.0051 (13)	−0.0200 (14)
C7	0.0656 (17)	0.0617 (18)	0.0441 (16)	−0.0180 (15)	0.0041 (14)	−0.0149 (14)
C8	0.0527 (16)	0.0623 (18)	0.0592 (18)	−0.0135 (14)	0.0050 (14)	−0.0273 (15)
C9	0.0607 (16)	0.0543 (16)	0.0512 (16)	−0.0170 (14)	0.0047 (14)	−0.0160 (14)
C10	0.117 (3)	0.082 (2)	0.121 (3)	−0.005 (2)	−0.033 (3)	0.005 (2)
C11	0.0613 (18)	0.0593 (19)	0.0583 (18)	−0.0161 (15)	−0.0014 (15)	−0.0173 (15)
C12	0.0532 (17)	0.076 (2)	0.075 (2)	−0.0103 (15)	−0.0054 (15)	−0.0256 (18)
C13	0.0562 (19)	0.088 (2)	0.097 (2)	−0.0291 (18)	0.0082 (18)	−0.030 (2)
C14	0.0591 (18)	0.0647 (19)	0.086 (2)	−0.0271 (16)	0.0036 (16)	−0.0172 (17)
C15	0.0527 (16)	0.0530 (16)	0.0543 (16)	−0.0208 (13)	0.0028 (13)	−0.0176 (14)
C16	0.0481 (16)	0.0660 (18)	0.0525 (16)	−0.0204 (14)	0.0039 (13)	−0.0236 (14)
C17	0.0643 (18)	0.0588 (17)	0.0540 (17)	−0.0225 (15)	0.0071 (14)	−0.0192 (14)
C18	0.0551 (16)	0.0551 (16)	0.0571 (16)	−0.0163 (14)	0.0036 (13)	−0.0197 (14)
C19	0.164 (4)	0.111 (3)	0.124 (3)	−0.049 (3)	−0.046 (3)	−0.046 (3)
C20	0.076 (2)	0.0602 (19)	0.067 (2)	−0.0202 (16)	−0.0088 (16)	−0.0167 (17)
C21	0.084 (2)	0.0555 (19)	0.097 (3)	−0.0239 (17)	−0.0023 (19)	−0.0208 (19)
C22	0.096 (2)	0.064 (2)	0.088 (3)	−0.0369 (18)	0.005 (2)	−0.0059 (19)
C23	0.084 (2)	0.070 (2)	0.0649 (19)	−0.0292 (17)	0.0038 (16)	−0.0058 (17)
C24	0.0545 (15)	0.0473 (16)	0.0500 (17)	−0.0126 (13)	0.0033 (13)	−0.0084 (13)
C25	0.0637 (17)	0.0510 (17)	0.0593 (18)	−0.0201 (14)	−0.0005 (14)	−0.0060 (15)
C26	0.0529 (16)	0.0597 (17)	0.0521 (16)	−0.0138 (14)	0.0036 (13)	−0.0132 (14)
C27	0.0687 (17)	0.0664 (17)	0.0486 (16)	−0.0295 (15)	−0.0004 (13)	−0.0130 (14)
C28	0.087 (2)	0.094 (2)	0.097 (2)	−0.0184 (19)	0.023 (2)	−0.050 (2)
C29	0.0546 (17)	0.0526 (16)	0.0486 (16)	−0.0155 (13)	0.0055 (14)	−0.0091 (13)
C30	0.0521 (18)	0.0663 (19)	0.076 (2)	−0.0059 (14)	0.0028 (16)	−0.0117 (17)
C31	0.0482 (18)	0.095 (2)	0.087 (2)	−0.0025 (16)	−0.0133 (17)	−0.021 (2)
C32	0.0580 (18)	0.084 (2)	0.0589 (18)	−0.0105 (16)	−0.0107 (15)	−0.0164 (16)
C33	0.0467 (15)	0.0541 (16)	0.0467 (15)	−0.0128 (13)	−0.0049 (13)	−0.0088 (13)
C34	0.0379 (14)	0.0488 (15)	0.0529 (16)	−0.0134 (12)	−0.0039 (13)	−0.0048 (13)
C35	0.0574 (17)	0.0608 (17)	0.0476 (16)	−0.0183 (14)	−0.0043 (14)	−0.0130 (14)
C36	0.0566 (16)	0.0681 (18)	0.0516 (16)	−0.0115 (14)	0.0032 (14)	−0.0183 (14)
C37	0.0524 (15)	0.0493 (15)	0.0433 (15)	−0.0156 (13)	0.0027 (13)	−0.0120 (13)
N1	0.0511 (13)	0.0596 (14)	0.0513 (13)	−0.0157 (11)	0.0025 (11)	−0.0175 (11)
N2	0.0651 (14)	0.0654 (15)	0.0520 (13)	−0.0311 (12)	0.0027 (11)	−0.0123 (12)
N3	0.0477 (13)	0.0636 (14)	0.0534 (13)	−0.0122 (11)	0.0016 (11)	−0.0162 (11)
N4	0.0533 (13)	0.0612 (14)	0.0519 (14)	−0.0156 (11)	0.0086 (11)	−0.0182 (12)
O1	0.0758 (14)	0.0767 (14)	0.0974 (16)	−0.0167 (12)	−0.0118 (12)	0.0055 (13)
O2	0.0564 (11)	0.0705 (12)	0.0794 (13)	−0.0261 (10)	0.0020 (10)	−0.0061 (10)
O3	0.1308 (19)	0.1312 (19)	0.0715 (14)	−0.0868 (17)	0.0009 (13)	−0.0134 (14)
O4	0.0976 (14)	0.0991 (15)	0.0501 (12)	−0.0504 (12)	−0.0052 (10)	−0.0104 (11)
O5	0.0691 (12)	0.0804 (14)	0.0596 (12)	−0.0096 (11)	0.0072 (10)	−0.0249 (11)
O6	0.0455 (10)	0.0858 (13)	0.0635 (11)	−0.0079 (9)	−0.0075 (9)	−0.0268 (10)
O7	0.1317 (18)	0.0847 (14)	0.0563 (12)	−0.0599 (14)	−0.0076 (12)	−0.0072 (11)
O8	0.149 (2)	0.0852 (15)	0.0793 (16)	−0.0509 (15)	−0.0278 (14)	−0.0184 (13)

Geometric parameters (Å, º) top

C1—O3	1.401 (3)	C19—H19B	0.9600
C1—H1A	0.9600	C19—H19C	0.9600
C1—H1B	0.9600	C20—O8	1.362 (3)
C1—H1C	0.9600	C20—C21	1.375 (3)
C2—O3	1.369 (3)	C20—C25	1.402 (4)
C2—C3	1.371 (3)	C21—C22	1.381 (4)
C2—C7	1.400 (3)	C21—H21	0.9300
C3—C4	1.381 (4)	C22—C23	1.373 (4)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.369 (3)	C23—C24	1.396 (3)
C4—H4A	0.9300	C23—H23	0.9300
C5—C6	1.397 (3)	C24—C25	1.387 (3)
C5—H5	0.9300	C24—C26	1.453 (3)
C6—C7	1.397 (3)	C25—O7	1.353 (3)
C6—C8	1.447 (3)	C26—N2	1.270 (3)
C7—O4	1.346 (3)	C26—H26	0.9300
C8—N4	1.270 (3)	C27—N2	1.469 (3)
C8—H8	0.9300	C27—C37	1.535 (3)
C9—N4	1.457 (3)	C27—H27A	0.9700
C9—C37	1.535 (3)	C27—H27B	0.9700
C9—H9A	0.9700	C28—O5	1.415 (3)
C9—H9B	0.9700	C28—H28A	0.9600
C10—O1	1.390 (3)	C28—H28B	0.9600
C10—H10A	0.9600	C28—H28C	0.9600
C10—H10B	0.9600	C29—O5	1.372 (3)
C10—H10C	0.9600	C29—C30	1.378 (3)
C11—C12	1.371 (3)	C29—C34	1.389 (3)
C11—O1	1.380 (3)	C30—C31	1.381 (4)
C11—C16	1.392 (3)	C30—H30	0.9300
C12—C13	1.379 (4)	C31—C32	1.363 (4)
C12—H12	0.9300	C31—H31	0.9300
C13—C14	1.365 (4)	C32—C33	1.397 (3)
C13—H13	0.9300	C32—H32	0.9300
C14—C15	1.391 (3)	C33—C34	1.393 (3)
C14—H14	0.9300	C33—C35	1.452 (3)
C15—C16	1.396 (3)	C34—O6	1.353 (3)
C15—C17	1.447 (3)	C35—N3	1.270 (3)
C16—O2	1.356 (3)	C35—H35	0.9300
C17—N1	1.275 (3)	C36—N3	1.468 (3)
C17—H17	0.9300	C36—C37	1.525 (3)
C18—N1	1.454 (3)	C36—H36A	0.9700
C18—C37	1.534 (3)	C36—H36B	0.9700
C18—H18A	0.9700	O2—H2	0.8200
C18—H18B	0.9700	O4—H4	0.8200
C19—O8	1.432 (3)	O6—H6	0.8200
C19—H19A	0.9600	O7—H7	0.8200

O3—C1—H1A	109.5	C20—C21—C22	121.1 (3)
O3—C1—H1B	109.5	C20—C21—H21	119.5
H1A—C1—H1B	109.5	C22—C21—H21	119.5
O3—C1—H1C	109.5	C23—C22—C21	119.4 (3)
H1A—C1—H1C	109.5	C23—C22—H22	120.3
H1B—C1—H1C	109.5	C21—C22—H22	120.3
O3—C2—C3	125.3 (3)	C22—C23—C24	121.1 (3)
O3—C2—C7	114.8 (2)	C22—C23—H23	119.5
C3—C2—C7	119.8 (3)	C24—C23—H23	119.4
C2—C3—C4	120.6 (3)	C25—C24—C23	118.9 (2)
C2—C3—H3	119.7	C25—C24—C26	121.4 (2)
C4—C3—H3	119.7	C23—C24—C26	119.8 (2)
C5—C4—C3	120.3 (3)	O7—C25—C24	121.4 (2)
C5—C4—H4A	119.8	O7—C25—C20	118.3 (3)
C3—C4—H4A	119.8	C24—C25—C20	120.2 (3)
C4—C5—C6	120.4 (3)	N2—C26—C24	123.1 (2)
C4—C5—H5	119.8	N2—C26—H26	118.4
C6—C5—H5	119.8	C24—C26—H26	118.4
C7—C6—C5	119.1 (2)	N2—C27—C37	112.89 (19)
C7—C6—C8	120.2 (2)	N2—C27—H27A	109.0
C5—C6—C8	120.7 (2)	C37—C27—H27A	109.0
O4—C7—C6	122.0 (2)	N2—C27—H27B	109.0
O4—C7—C2	118.3 (2)	C37—C27—H27B	109.0
C6—C7—C2	119.6 (2)	H27A—C27—H27B	107.8
N4—C8—C6	122.1 (2)	O5—C28—H28A	109.5
N4—C8—H8	118.9	O5—C28—H28B	109.5
C6—C8—H8	118.9	H28A—C28—H28B	109.5
N4—C9—C37	111.28 (19)	O5—C28—H28C	109.5
N4—C9—H9A	109.4	H28A—C28—H28C	109.5
C37—C9—H9A	109.4	H28B—C28—H28C	109.5
N4—C9—H9B	109.4	O5—C29—C30	124.4 (3)
C37—C9—H9B	109.4	O5—C29—C34	115.6 (2)
H9A—C9—H9B	108.0	C30—C29—C34	120.0 (3)
O1—C10—H10A	109.5	C29—C30—C31	119.8 (3)
O1—C10—H10B	109.5	C29—C30—H30	120.1
H10A—C10—H10B	109.5	C31—C30—H30	120.1
O1—C10—H10C	109.5	C32—C31—C30	120.9 (3)
H10A—C10—H10C	109.5	C32—C31—H31	119.5
H10B—C10—H10C	109.5	C30—C31—H31	119.5
C12—C11—O1	125.0 (3)	C31—C32—C33	120.2 (3)
C12—C11—C16	120.1 (3)	C31—C32—H32	119.9
O1—C11—C16	114.9 (2)	C33—C32—H32	119.9
C11—C12—C13	120.2 (3)	C34—C33—C32	119.1 (3)
C11—C12—H12	119.9	C34—C33—C35	121.7 (2)
C13—C12—H12	119.9	C32—C33—C35	119.2 (2)
C14—C13—C12	120.3 (3)	O6—C34—C29	118.8 (2)
C14—C13—H13	119.9	O6—C34—C33	121.2 (2)
C12—C13—H13	119.9	C29—C34—C33	120.0 (2)
C13—C14—C15	120.8 (3)	N3—C35—C33	123.2 (2)
C13—C14—H14	119.6	N3—C35—H35	118.4
C15—C14—H14	119.6	C33—C35—H35	118.4
C14—C15—C16	118.7 (2)	N3—C36—C37	113.1 (2)
C14—C15—C17	120.3 (2)	N3—C36—H36A	109.0
C16—C15—C17	120.9 (2)	C37—C36—H36A	109.0
O2—C16—C11	118.4 (2)	N3—C36—H36B	109.0
O2—C16—C15	121.8 (2)	C37—C36—H36B	109.0
C11—C16—C15	119.8 (2)	H36A—C36—H36B	107.8
N1—C17—C15	122.3 (2)	C36—C37—C18	109.1 (2)
N1—C17—H17	118.8	C36—C37—C27	111.42 (19)
C15—C17—H17	118.8	C18—C37—C27	107.39 (18)
N1—C18—C37	111.7 (2)	C36—C37—C9	108.6 (2)
N1—C18—H18A	109.3	C18—C37—C9	110.63 (19)
C37—C18—H18A	109.3	C27—C37—C9	109.64 (19)
N1—C18—H18B	109.3	C17—N1—C18	119.5 (2)
C37—C18—H18B	109.3	C26—N2—C27	116.9 (2)
H18A—C18—H18B	107.9	C35—N3—C36	117.2 (2)
O8—C19—H19A	109.5	C8—N4—C9	120.7 (2)
O8—C19—H19B	109.5	C11—O1—C10	118.6 (2)
H19A—C19—H19B	109.5	C16—O2—H2	109.5
O8—C19—H19C	109.5	C2—O3—C1	118.8 (2)
H19A—C19—H19C	109.5	C7—O4—H4	109.5
H19B—C19—H19C	109.5	C29—O5—C28	118.0 (2)
O8—C20—C21	125.5 (3)	C34—O6—H6	109.5
O8—C20—C25	115.1 (3)	C25—O7—H7	109.5
C21—C20—C25	119.3 (3)	C20—O8—C19	117.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.87	2.592 (3)	147
O4—H4···N4	0.82	1.84	2.567 (2)	147
O6—H6···N3	0.82	1.89	2.623 (3)	148
O7—H7···N2	0.82	1.88	2.612 (3)	148
C27—H27B···N1	0.97	2.56	2.936 (3)	103
C26—H26···O5ⁱ	0.93	2.58	3.309 (3)	136
C28—H28C···O2ⁱ	0.96	2.57	3.387 (3)	143
C12—H12···O6ⁱⁱ	0.93	2.59	3.400 (3)	146
C32—H32···O3ⁱⁱⁱ	0.93	2.42	3.289 (3)	155
C36—H36B···O8^iv	0.97	2.55	3.399 (3)	146

Symmetry codes: (i) −x, −y+2, −z; (ii) −x−1, −y+2, −z; (iii) x+1, y, z; (iv) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₃₇H₄₀N₄O₈
M_r	668.73
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	11.3464 (11), 12.4437 (12), 13.0523 (14)
α, β, γ (°)	75.861 (7), 88.893 (7), 78.385 (7)
V (Å³)	1749.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.18 × 0.16 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.984, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	16510, 6221, 3077
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.145, 0.94
No. of reflections	6194
No. of parameters	443
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.87	2.592 (3)	146.9
O4—H4···N4	0.82	1.84	2.567 (2)	147.3
O6—H6···N3	0.82	1.89	2.623 (3)	147.5
O7—H7···N2	0.82	1.88	2.612 (3)	147.5
C27—H27B···N1	0.97	2.56	2.936 (3)	103.4
C26—H26···O5ⁱ	0.93	2.58	3.309 (3)	135.7
C28—H28C···O2ⁱ	0.96	2.57	3.387 (3)	142.9
C12—H12···O6ⁱⁱ	0.93	2.59	3.400 (3)	145.9
C32—H32···O3ⁱⁱⁱ	0.93	2.42	3.289 (3)	154.9
C36—H36B···O8^iv	0.97	2.55	3.399 (3)	146.3

Symmetry codes: (i) −x, −y+2, −z; (ii) −x−1, −y+2, −z; (iii) x+1, y, z; (iv) −x, −y+2, −z+1.

References

Bernardo, K., Leppard, S., Robert, A., Commenges, G., Dahan, F. & Meunier, B. (1996). Inorg. Chem. 35, 387–396. CSD CrossRef PubMed CAS Web of Science Google Scholar
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Laliberte, D., Maris, T. & Wuest, J. D. (2004). J. Org. Chem. 69, 1776–1787. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tanaka, T., Yasuda, Y. & Hayashi, M. (2006). J. Org. Chem. 71, 7091–7093. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 64| Part 8| August 2008| Page o1455

doi:10.1107/S1600536808020618

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

A four-armed Schiff base: 6,6′,6′′,6′′′-tetra­meth­­oxy-2,2′,2′′,2′′′-[methane­tetra­yltetra­kis(methylene­nitrilo­methyl­­idyne)]tetra­phenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

A four-armed Schiff base: 6,6′,6′′,6′′′-tetramethoxy-2,2′,2′′,2′′′-[methanetetrayltetrakis(methylenenitrilomethylidyne)]tetraphenol