N,N,N′,N′-Tetra­kis(benzimidazol-2-ylmeth­yl)ethane-1,2-diamine methanol tetra­solvate dihydrate

Pei, Y.-M.; Meng, X.-G.; Zhou, C.-S.

doi:10.1107/S1600536807038111

Buy article online - an online subscription or single-article purchase is required to access this article.

N,N,N′,N′-Tetrakis(benzimidazol-2-ylmethyl)ethane-1,2-diamine methanol tetrasolvate dihydrate

Y.-M. Pei, X.-G. Meng and C.-S. Zhou

The title compound, C₃₄H₃₂N₁₀·4CH₄O·2H₂O, crystallizes with the mid-point of the central C—C bond of the tetrabenzimidazolylethanediamine molecule located on an inversion centre. The crystal packing is stabilized by O(or N)—H

O and O—H

N hydrogen bonds.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038111/lh2470sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038111/lh2470Isup2.hkl Contains datablock I

CCDC reference: 660253

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R factor = 0.059
wR factor = 0.163
Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          7

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

As part of our continuing studies on the ligands or metal complexes containing multi-benzimidazole groups (Chen et al., 2004;Liao et al.,2001), we report here the crystal structure of the related title compound, which was obtained unexpectedly by reacting N,N,N ', N' - tetrakis (2 '-benzimidazolyl methyl) -1,2-ethanediamine (EDTB) with Mn (NO₃)₂ ˙4H₂O in CH₃OH and H₂O solution.

In the molecule (Fig. 1), the N2/N3/C3—C9 benzimidazole ring is twisted from the benzimidazole ring (N4/N5/C11—C17) by a dihedral angle of 47.1 (1)°. In the asymmetric unit, there is half of an EDTB molecule, two methanol and one water solvent molecules.

In the supramolecular structure, by a combination of O(or N)–H···O, and O–H···N hydrogen bonds the molecules are linked into a three-dimensional framework (Fig.2). Analysis using PLATON (Spek, 2003) shows that no π–π and C–H···π interactions are observed in the crystal structure.

Related literature top

For related literature, see: Chen et al. (2004); Hendriks et al. (1982); Liao et al. (2001).

Experimental top

Chemicals of reagent grade were used without further purification. The ligand N,N,N ', N' - tetrakis (2 '-benzimidazolyl methyl) -1,2-ethanediamine (EDTB) was synthesized from reported literature earlier (Hendriks, et al.,1982). The title pink salt was obtained unexpectedly by reacting EDTB (0.29 g, 0.5 mmol) in 20 ml hot methanol with Mn (NO₃)₂ ˙4H₂O (0.25 g, 1.0 mmol) solution of 10 ml H₂O. The mixture was stirred for 1 h at 303k and then filtered. The resulting pink solution was allowed to stand at room temperature for 1 week. Crystals suitale for X-ray analysis were obtained at the bottom of the vessel.

Structure description top

For related literature, see: Chen et al. (2004); Hendriks et al. (1982); Liao et al. (2001).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures top

	Fig. 1. View of the title molecular structure, showing 50% probability displacement ellipsoids and H atoms as small spheres. Atoms labeled with suffix 'a' are related by the symmetry operator (-x, -y, -z + 1).
	Fig. 2. Part of the crystal structure showing the formation of the three-dimensinal network. Hydrogen bonds are shown as dashed lines.

N,N,N',N'-Tetrakis(benzimidazol-2-ylmethyl)ethane-1,2-diamine methanol tetrasolvate dihydrate top

Crystal data top

C₃₄H₃₂N₁₀·4CH₄O·2H₂O	Z = 1
M_r = 744.90	F(000) = 398
Triclinic, P1	D_x = 1.183 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2349 (6) Å	Cell parameters from 3273 reflections
b = 10.4290 (7) Å	θ = 2.3–24.9°
c = 11.5344 (8) Å	µ = 0.08 mm⁻¹
α = 100.500 (1)°	T = 296 K
β = 101.763 (1)°	Block, pink
γ = 99.417 (1)°	0.20 × 0.20 × 0.10 mm
V = 1045.83 (12) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4083 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	2726 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.094
0.3° wide ω exposures scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→11
T_min = 0.984, T_max = 0.992	k = −12→12
10988 measured reflections	l = −14→14

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.087P)²] where P = (F_o² + 2F_c²)/3
4083 reflections	(Δ/σ)_max < 0.001
264 parameters	Δρ_max = 0.23 e Å⁻³
7 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₃₄H₃₂N₁₀·4CH₄O·2H₂O	γ = 99.417 (1)°
M_r = 744.90	V = 1045.83 (12) Å³
Triclinic, P1	Z = 1
a = 9.2349 (6) Å	Mo Kα radiation
b = 10.4290 (7) Å	µ = 0.08 mm⁻¹
c = 11.5344 (8) Å	T = 296 K
α = 100.500 (1)°	0.20 × 0.20 × 0.10 mm
β = 101.763 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4083 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	2726 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.992	R_int = 0.094
10988 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	7 restraints
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.23 e Å⁻³
4083 reflections	Δρ_min = −0.26 e Å⁻³
264 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	0.0644 (2)	0.05926 (17)	0.52781 (15)	0.0480 (4)
H1A	0.0399	0.1163	0.5943	0.058*
H1B	0.1549	0.0289	0.5604	0.058*
C2	0.1912 (2)	0.0801 (2)	0.36638 (17)	0.0568 (5)
H2A	0.1693	−0.0161	0.3554	0.068*
H2B	0.2955	0.1131	0.4118	0.068*
C3	0.1733 (2)	0.11411 (17)	0.24450 (16)	0.0503 (5)
C4	0.0658 (2)	0.16310 (17)	0.07461 (16)	0.0545 (5)
C5	−0.0262 (3)	0.1985 (2)	−0.01979 (18)	0.0683 (6)
H5	−0.1238	0.2093	−0.0182	0.082*
C6	0.0359 (4)	0.2169 (2)	−0.11684 (19)	0.0812 (7)
H6	−0.0208	0.2428	−0.1815	0.097*
C7	0.1793 (4)	0.1977 (3)	−0.1200 (2)	0.0887 (8)
H7	0.2159	0.2091	−0.1876	0.106*
C8	0.2696 (3)	0.1622 (2)	−0.0263 (2)	0.0758 (7)
H8	0.3660	0.1491	−0.0295	0.091*
C9	0.2119 (2)	0.14626 (18)	0.07405 (17)	0.0567 (5)
C10	0.1497 (2)	0.27781 (18)	0.49058 (18)	0.0553 (5)
H10A	0.1750	0.3237	0.4291	0.066*
H10B	0.2408	0.2903	0.5542	0.066*
C11	0.0337 (2)	0.33503 (17)	0.54216 (17)	0.0504 (5)
C12	−0.0839 (2)	0.43572 (17)	0.66124 (17)	0.0550 (5)
C13	−0.1279 (3)	0.5076 (2)	0.7564 (2)	0.0724 (6)
H13	−0.0576	0.5504	0.8287	0.087*
C14	−0.2771 (3)	0.5143 (2)	0.7419 (2)	0.0815 (7)
H14	−0.3078	0.5633	0.8048	0.098*
C15	−0.3834 (3)	0.4495 (2)	0.6349 (3)	0.0812 (7)
H15	−0.4841	0.4557	0.6277	0.097*
C16	−0.3428 (3)	0.3760 (2)	0.5389 (2)	0.0719 (6)
H16	−0.4138	0.3326	0.4671	0.086*
C17	−0.1918 (2)	0.36981 (18)	0.55440 (18)	0.0552 (5)
C18	0.4678 (4)	0.8728 (4)	0.2625 (4)	0.1300 (12)
H18A	0.5412	0.8183	0.2553	0.195*
H18B	0.3708	0.8250	0.2126	0.195*
H18C	0.4617	0.8944	0.3457	0.195*
C19	0.6472 (5)	0.4394 (4)	0.0909 (4)	0.174 (2)
H19A	0.6046	0.5171	0.1058	0.261*
H19B	0.5715	0.3674	0.0368	0.261*
H19C	0.7307	0.4586	0.0546	0.261*
N1	0.09316 (17)	0.13561 (13)	0.43655 (12)	0.0474 (4)
N2	0.27737 (18)	0.11545 (16)	0.18230 (14)	0.0581 (4)
N3	0.04414 (19)	0.14113 (15)	0.18572 (13)	0.0521 (4)
H3A	−0.040 (2)	0.151 (2)	0.2111 (18)	0.063*
N4	0.05769 (19)	0.41225 (14)	0.65166 (14)	0.0560 (4)
N5	−0.11288 (19)	0.30662 (16)	0.48112 (15)	0.0553 (4)
H5A	−0.143 (2)	0.259 (2)	0.4045 (18)	0.066*
O1	0.75915 (17)	0.17048 (18)	0.23664 (15)	0.0740 (5)
H1C	0.732 (3)	0.238 (3)	0.209 (3)	0.111*
H1D	0.682 (3)	0.114 (3)	0.236 (3)	0.111*
O2	0.6956 (3)	0.4047 (2)	0.1961 (3)	0.1419 (10)
H2C	0.771 (4)	0.468 (4)	0.242 (4)	0.213*
O3	0.5088 (2)	0.9845 (3)	0.2266 (3)	0.1536 (11)
H3B	0.444 (5)	1.036 (5)	0.228 (5)	0.230*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0588 (12)	0.0470 (9)	0.0433 (9)	0.0109 (8)	0.0137 (8)	0.0211 (7)
C2	0.0630 (13)	0.0591 (11)	0.0616 (11)	0.0201 (10)	0.0246 (10)	0.0293 (9)
C3	0.0565 (12)	0.0468 (10)	0.0556 (10)	0.0122 (8)	0.0237 (9)	0.0191 (8)
C4	0.0748 (14)	0.0404 (10)	0.0487 (10)	0.0055 (9)	0.0194 (9)	0.0117 (8)
C5	0.0903 (16)	0.0552 (12)	0.0555 (12)	0.0125 (11)	0.0105 (11)	0.0131 (10)
C6	0.126 (2)	0.0644 (14)	0.0463 (12)	0.0075 (15)	0.0132 (13)	0.0163 (10)
C7	0.127 (2)	0.0845 (17)	0.0526 (13)	−0.0038 (16)	0.0335 (15)	0.0189 (12)
C8	0.0915 (17)	0.0760 (15)	0.0612 (13)	0.0005 (12)	0.0367 (12)	0.0132 (11)
C9	0.0719 (14)	0.0471 (10)	0.0533 (11)	0.0031 (9)	0.0260 (10)	0.0126 (8)
C10	0.0591 (12)	0.0495 (10)	0.0592 (11)	0.0036 (9)	0.0151 (9)	0.0228 (9)
C11	0.0597 (13)	0.0377 (9)	0.0538 (10)	0.0040 (8)	0.0102 (9)	0.0193 (8)
C12	0.0716 (14)	0.0396 (10)	0.0559 (11)	0.0100 (9)	0.0155 (10)	0.0175 (8)
C13	0.0969 (19)	0.0534 (12)	0.0660 (13)	0.0141 (12)	0.0204 (12)	0.0115 (10)
C14	0.105 (2)	0.0613 (14)	0.0914 (18)	0.0244 (14)	0.0462 (17)	0.0193 (13)
C15	0.0784 (17)	0.0675 (14)	0.109 (2)	0.0199 (13)	0.0368 (16)	0.0287 (14)
C16	0.0683 (15)	0.0625 (13)	0.0814 (15)	0.0101 (11)	0.0125 (12)	0.0162 (11)
C17	0.0639 (13)	0.0443 (10)	0.0593 (11)	0.0101 (9)	0.0143 (10)	0.0185 (9)
C18	0.103 (2)	0.124 (3)	0.196 (4)	0.043 (2)	0.055 (2)	0.079 (3)
C19	0.165 (4)	0.112 (3)	0.186 (4)	−0.004 (2)	−0.079 (3)	0.051 (3)
N1	0.0593 (10)	0.0430 (8)	0.0477 (8)	0.0106 (7)	0.0202 (7)	0.0213 (6)
N2	0.0597 (11)	0.0605 (10)	0.0618 (10)	0.0112 (8)	0.0267 (8)	0.0206 (8)
N3	0.0592 (11)	0.0527 (9)	0.0535 (9)	0.0142 (8)	0.0237 (8)	0.0209 (7)
N4	0.0680 (11)	0.0435 (8)	0.0539 (9)	0.0069 (8)	0.0099 (8)	0.0141 (7)
N5	0.0617 (11)	0.0506 (9)	0.0496 (9)	0.0078 (8)	0.0083 (8)	0.0102 (7)
O1	0.0586 (10)	0.0798 (11)	0.0793 (10)	0.0146 (8)	0.0091 (8)	0.0155 (9)
O2	0.1251 (19)	0.0802 (13)	0.171 (2)	−0.0134 (12)	−0.0549 (16)	0.0371 (14)
O3	0.0777 (15)	0.147 (2)	0.290 (3)	0.0454 (14)	0.0767 (18)	0.128 (2)

Geometric parameters (Å, º) top

C1—N1	1.471 (2)	C11—N5	1.349 (2)
C1—C1ⁱ	1.508 (4)	C12—C13	1.384 (3)
C1—H1A	0.9700	C12—N4	1.391 (3)
C1—H1B	0.9700	C12—C17	1.397 (3)
C2—N1	1.452 (2)	C13—C14	1.368 (3)
C2—C3	1.495 (2)	C13—H13	0.9300
C2—H2A	0.9700	C14—C15	1.389 (4)
C2—H2B	0.9700	C14—H14	0.9300
C3—N2	1.311 (2)	C15—C16	1.381 (3)
C3—N3	1.346 (2)	C15—H15	0.9300
C4—C5	1.384 (3)	C16—C17	1.383 (3)
C4—C9	1.389 (3)	C16—H16	0.9300
C4—N3	1.390 (2)	C17—N5	1.373 (2)
C5—C6	1.386 (3)	C18—O3	1.330 (4)
C5—H5	0.9300	C18—H18A	0.9600
C6—C7	1.378 (4)	C18—H18B	0.9600
C6—H6	0.9300	C18—H18C	0.9600
C7—C8	1.372 (4)	C19—O2	1.340 (4)
C7—H7	0.9300	C19—H19A	0.9600
C8—C9	1.394 (3)	C19—H19B	0.9600
C8—H8	0.9300	C19—H19C	0.9600
C9—N2	1.389 (3)	N3—H3A	0.899 (18)
C10—N1	1.462 (2)	N5—H5A	0.895 (19)
C10—C11	1.482 (3)	O1—H1C	0.87 (2)
C10—H10A	0.9700	O1—H1D	0.84 (2)
C10—H10B	0.9700	O2—H2C	0.88 (3)
C11—N4	1.323 (2)	O3—H3B	0.86 (3)

N1—C1—C1ⁱ	110.60 (17)	C13—C12—C17	119.8 (2)
N1—C1—H1A	109.5	N4—C12—C17	109.68 (16)
C1ⁱ—C1—H1A	109.5	C14—C13—C12	118.6 (2)
N1—C1—H1B	109.5	C14—C13—H13	120.7
C1ⁱ—C1—H1B	109.5	C12—C13—H13	120.7
H1A—C1—H1B	108.1	C13—C14—C15	121.3 (2)
N1—C2—C3	113.09 (14)	C13—C14—H14	119.4
N1—C2—H2A	109.0	C15—C14—H14	119.4
C3—C2—H2A	109.0	C16—C15—C14	121.4 (2)
N1—C2—H2B	109.0	C16—C15—H15	119.3
C3—C2—H2B	109.0	C14—C15—H15	119.3
H2A—C2—H2B	107.8	C15—C16—C17	117.0 (2)
N2—C3—N3	113.39 (16)	C15—C16—H16	121.5
N2—C3—C2	124.18 (17)	C17—C16—H16	121.5
N3—C3—C2	122.37 (15)	N5—C17—C16	132.83 (19)
C5—C4—C9	122.96 (18)	N5—C17—C12	105.11 (17)
C5—C4—N3	131.8 (2)	C16—C17—C12	122.06 (19)
C9—C4—N3	105.17 (17)	O3—C18—H18A	109.5
C4—C5—C6	116.0 (2)	O3—C18—H18B	109.5
C4—C5—H5	122.0	H18A—C18—H18B	109.5
C6—C5—H5	122.0	O3—C18—H18C	109.5
C7—C6—C5	121.8 (2)	H18A—C18—H18C	109.5
C7—C6—H6	119.1	H18B—C18—H18C	109.5
C5—C6—H6	119.1	O2—C19—H19A	109.5
C8—C7—C6	121.9 (2)	O2—C19—H19B	109.5
C8—C7—H7	119.1	H19A—C19—H19B	109.5
C6—C7—H7	119.1	O2—C19—H19C	109.5
C7—C8—C9	117.8 (2)	H19A—C19—H19C	109.5
C7—C8—H8	121.1	H19B—C19—H19C	109.5
C9—C8—H8	121.1	C2—N1—C10	112.26 (14)
N2—C9—C4	109.66 (15)	C2—N1—C1	111.51 (13)
N2—C9—C8	130.7 (2)	C10—N1—C1	111.94 (13)
C4—C9—C8	119.6 (2)	C3—N2—C9	105.00 (16)
N1—C10—C11	110.23 (15)	C3—N3—C4	106.77 (15)
N1—C10—H10A	109.6	C3—N3—H3A	129.9 (13)
C11—C10—H10A	109.6	C4—N3—H3A	123.2 (13)
N1—C10—H10B	109.6	C11—N4—C12	104.79 (16)
C11—C10—H10B	109.6	C11—N5—C17	107.78 (16)
H10A—C10—H10B	108.1	C11—N5—H5A	121.4 (13)
N4—C11—N5	112.63 (17)	C17—N5—H5A	130.7 (13)
N4—C11—C10	125.50 (18)	H1C—O1—H1D	110 (2)
N5—C11—C10	121.80 (17)	C19—O2—H2C	109 (3)
C13—C12—N4	130.5 (2)	C18—O3—H3B	114 (4)

N1—C2—C3—N2	156.56 (17)	C13—C12—C17—C16	1.4 (3)
N1—C2—C3—N3	−26.3 (3)	N4—C12—C17—C16	−179.99 (17)
C9—C4—C5—C6	−0.1 (3)	C3—C2—N1—C10	−77.3 (2)
N3—C4—C5—C6	177.65 (19)	C3—C2—N1—C1	156.14 (16)
C4—C5—C6—C7	1.5 (3)	C11—C10—N1—C2	169.89 (14)
C5—C6—C7—C8	−1.4 (4)	C11—C10—N1—C1	−63.81 (19)
C6—C7—C8—C9	−0.3 (4)	C1ⁱ—C1—N1—C2	−84.5 (2)
C5—C4—C9—N2	177.98 (17)	C1ⁱ—C1—N1—C10	148.77 (19)
N3—C4—C9—N2	−0.3 (2)	N3—C3—N2—C9	0.2 (2)
C5—C4—C9—C8	−1.5 (3)	C2—C3—N2—C9	177.57 (17)
N3—C4—C9—C8	−179.79 (18)	C4—C9—N2—C3	0.0 (2)
C7—C8—C9—N2	−177.7 (2)	C8—C9—N2—C3	179.5 (2)
C7—C8—C9—C4	1.7 (3)	N2—C3—N3—C4	−0.4 (2)
N1—C10—C11—N4	132.12 (17)	C2—C3—N3—C4	−177.79 (16)
N1—C10—C11—N5	−44.6 (2)	C5—C4—N3—C3	−177.6 (2)
N4—C12—C13—C14	−179.68 (19)	C9—C4—N3—C3	0.38 (19)
C17—C12—C13—C14	−1.4 (3)	N5—C11—N4—C12	−0.37 (19)
C12—C13—C14—C15	0.8 (3)	C10—C11—N4—C12	−177.35 (15)
C13—C14—C15—C16	−0.2 (4)	C13—C12—N4—C11	178.59 (18)
C14—C15—C16—C17	0.1 (3)	C17—C12—N4—C11	0.16 (18)
C15—C16—C17—N5	179.17 (19)	N4—C11—N5—C17	0.4 (2)
C15—C16—C17—C12	−0.7 (3)	C10—C11—N5—C17	177.55 (14)
C13—C12—C17—N5	−178.53 (16)	C16—C17—N5—C11	179.8 (2)
N4—C12—C17—N5	0.09 (19)	C12—C17—N5—C11	−0.30 (18)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···O2	0.87 (2)	1.85 (2)	2.702 (3)	164 (3)
O3—H3B···N2ⁱⁱ	0.86 (3)	1.90 (4)	2.731 (2)	163 (5)
N5—H5A···O1ⁱⁱⁱ	0.90 (2)	1.94 (2)	2.828 (2)	170 (2)
N3—H3A···O1ⁱⁱⁱ	0.90 (2)	1.97 (2)	2.862 (2)	170 (2)
O2—H2C···N4^iv	0.88 (3)	1.89 (3)	2.765 (3)	173 (5)
O1—H1D···O3^v	0.84 (2)	1.89 (2)	2.731 (3)	177 (3)

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

Experimental details

Crystal data
Chemical formula	C₃₄H₃₂N₁₀·4CH₄O·2H₂O
M_r	744.90
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.2349 (6), 10.4290 (7), 11.5344 (8)
α, β, γ (°)	100.500 (1), 101.763 (1), 99.417 (1)
V (Å³)	1045.83 (12)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.984, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	10988, 4083, 2726
R_int	0.094
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.163, 1.01
No. of reflections	4083
No. of parameters	264
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.26

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···O2	0.87 (2)	1.85 (2)	2.702 (3)	164 (3)
O3—H3B···N2ⁱ	0.86 (3)	1.90 (4)	2.731 (2)	163 (5)
N5—H5A···O1ⁱⁱ	0.895 (19)	1.94 (2)	2.828 (2)	169.5 (19)
N3—H3A···O1ⁱⁱ	0.899 (18)	1.972 (19)	2.862 (2)	170.0 (18)
O2—H2C···N4ⁱⁱⁱ	0.88 (3)	1.89 (3)	2.765 (3)	173 (5)
O1—H1D···O3^iv	0.84 (2)	1.89 (2)	2.731 (3)	177 (3)

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

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page