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The title compound, C34H32N10·2C2H6O2, crystallizes in space group P \overline 1, with the main mol­ecule on an inversion centre. The crystal packing is stabilized by intermolecular N—H...O and O—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804012826/cv6318sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804012826/cv6318Isup2.hkl
Contains datablock I

CCDC reference: 242371

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.069
  • wR factor = 0.250
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

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Alert level C PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.91 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 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

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1999); software used to prepare material for publication: SHELXTL/PC.

N,N,N',N'-Tetrakis[(1H-benzimidazol-2-yl)methyl]ethane-1,2-diamine glycol disolvate top
Crystal data top
C34H32N10·2C2H6O2Z = 1
Mr = 704.83F(000) = 374
Triclinic, P1Dx = 1.260 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2367 (15) ÅCell parameters from 1058 reflections
b = 9.7383 (16) Åθ = 2.3–20.6°
c = 11.5791 (19) ŵ = 0.09 mm1
α = 85.764 (3)°T = 298 K
β = 76.748 (3)°Block, colourless
γ = 66.394 (3)°0.33 × 0.33 × 0.12 mm
V = 928.8 (3) Å3
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
2992 independent reflections
Radiation source: fine-focus sealed tube2074 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
h = 1010
Tmin = 0.973, Tmax = 0.990k = 1111
4360 measured reflectionsl = 1310
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.250H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.1469P)2 + 0.1154P]
where P = (Fo2 + 2Fc2)/3
2992 reflections(Δ/σ)max < 0.001
237 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.28 e Å3
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
xyzUiso*/Ueq
C10.2053 (4)0.4922 (4)0.2594 (3)0.0535 (9)
C20.1950 (4)0.3802 (4)0.4297 (3)0.0540 (9)
C30.1825 (5)0.2893 (5)0.5258 (4)0.0717 (11)
H30.14580.21360.52390.086*
C40.2272 (6)0.3164 (6)0.6243 (4)0.0889 (14)
H40.21980.25740.69050.107*
C50.2817 (6)0.4262 (6)0.6289 (4)0.0883 (14)
H50.31050.43990.69770.106*
C60.2951 (5)0.5171 (5)0.5346 (4)0.0797 (13)
H60.33080.59310.53830.096*
C70.2529 (4)0.4906 (4)0.4331 (3)0.0577 (9)
C80.1841 (5)0.5368 (4)0.1367 (3)0.0632 (10)
H8A0.08360.62420.14080.076*
H8B0.27190.56480.09560.076*
C90.0889 (4)0.4788 (4)0.0245 (3)0.0534 (9)
H9A0.12660.40440.08770.064*
H9B0.10710.56630.05770.064*
C100.3460 (4)0.3086 (4)0.0211 (3)0.0577 (9)
H10A0.40310.27440.08520.069*
H10B0.40390.35650.03670.069*
C110.3434 (4)0.1777 (4)0.0358 (3)0.0513 (8)
C120.2863 (4)0.0055 (4)0.0750 (3)0.0575 (9)
C130.2256 (5)0.1141 (5)0.0743 (4)0.0800 (12)
H130.14910.12380.00990.096*
C140.2829 (5)0.2078 (5)0.1726 (5)0.0874 (14)
H140.24500.28280.17420.105*
C150.3960 (5)0.1928 (5)0.2698 (4)0.0762 (12)
H150.43040.25660.33540.091*
C160.4574 (4)0.0870 (4)0.2707 (3)0.0655 (10)
H160.53440.07800.33510.079*
C170.4003 (4)0.0072 (4)0.1715 (3)0.0535 (9)
N10.1662 (3)0.3836 (3)0.3178 (2)0.0552 (8)
H10.12990.32680.29060.066*
N20.2592 (3)0.5606 (3)0.3225 (3)0.0625 (8)
N30.4350 (3)0.1236 (3)0.1438 (2)0.0544 (8)
H3A0.50280.15610.18760.065*
N40.2519 (3)0.1040 (3)0.0094 (3)0.0616 (8)
N50.1809 (3)0.4180 (3)0.0683 (2)0.0507 (7)
C180.0603 (6)1.0397 (6)0.3095 (5)0.0934 (14)
H18A0.01650.99980.25810.112*
H18B0.02721.09070.37590.112*
C190.1834 (7)0.9153 (6)0.3547 (5)0.1043 (17)
H19A0.23540.95490.39950.125*
H19B0.13130.85950.40880.125*
O10.1136 (5)1.1449 (4)0.2466 (3)0.1031 (11)
H1A0.15541.11550.17760.155*
O20.3022 (4)0.8170 (3)0.2660 (3)0.0987 (11)
H20.29430.73570.27130.148*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.063 (2)0.0491 (19)0.047 (2)0.0179 (16)0.0149 (16)0.0024 (16)
C20.0553 (19)0.053 (2)0.047 (2)0.0151 (16)0.0093 (16)0.0067 (16)
C30.077 (2)0.063 (2)0.056 (2)0.0142 (19)0.001 (2)0.0068 (19)
C40.112 (3)0.085 (3)0.050 (3)0.016 (3)0.022 (2)0.001 (2)
C50.095 (3)0.112 (4)0.052 (3)0.029 (3)0.021 (2)0.015 (3)
C60.084 (3)0.097 (3)0.060 (3)0.035 (2)0.013 (2)0.021 (2)
C70.060 (2)0.063 (2)0.046 (2)0.0211 (17)0.0062 (16)0.0108 (17)
C80.079 (2)0.051 (2)0.056 (2)0.0200 (18)0.0172 (19)0.0034 (17)
C90.0669 (19)0.0511 (19)0.0374 (18)0.0179 (16)0.0139 (15)0.0058 (15)
C100.0568 (19)0.061 (2)0.055 (2)0.0207 (16)0.0170 (16)0.0007 (17)
C110.0538 (18)0.0464 (19)0.0476 (19)0.0130 (15)0.0113 (15)0.0013 (15)
C120.0544 (19)0.051 (2)0.062 (2)0.0159 (16)0.0098 (17)0.0056 (17)
C130.077 (3)0.072 (3)0.092 (3)0.040 (2)0.004 (2)0.014 (2)
C140.084 (3)0.069 (3)0.122 (4)0.040 (2)0.023 (3)0.010 (3)
C150.074 (2)0.067 (3)0.087 (3)0.025 (2)0.016 (2)0.018 (2)
C160.062 (2)0.066 (2)0.060 (2)0.0188 (18)0.0047 (18)0.0078 (19)
C170.0514 (18)0.0446 (18)0.058 (2)0.0117 (14)0.0126 (16)0.0007 (16)
N10.0620 (17)0.0524 (17)0.0527 (18)0.0225 (13)0.0133 (14)0.0069 (14)
N20.0720 (19)0.0610 (19)0.0583 (19)0.0298 (15)0.0105 (15)0.0126 (15)
N30.0583 (16)0.0501 (16)0.0519 (17)0.0208 (13)0.0073 (13)0.0007 (13)
N40.0655 (18)0.0571 (18)0.0576 (19)0.0217 (15)0.0081 (14)0.0037 (15)
N50.0646 (16)0.0412 (14)0.0407 (15)0.0117 (12)0.0178 (13)0.0003 (12)
C180.092 (3)0.093 (4)0.085 (3)0.043 (3)0.009 (3)0.002 (3)
C190.127 (4)0.098 (4)0.081 (3)0.051 (3)0.009 (3)0.011 (3)
O10.174 (3)0.085 (2)0.0628 (19)0.079 (2)0.007 (2)0.0130 (16)
O20.104 (2)0.083 (2)0.099 (2)0.0511 (18)0.0299 (18)0.0200 (19)
Geometric parameters (Å, º) top
C1—N21.315 (4)C11—N41.316 (4)
C1—N11.339 (4)C11—N31.347 (4)
C1—C81.488 (5)C12—C131.380 (5)
C2—N11.377 (4)C12—C171.385 (5)
C2—C31.384 (5)C12—N41.390 (4)
C2—C71.385 (5)C13—C141.379 (6)
C3—C41.374 (6)C13—H130.9300
C3—H30.9300C14—C151.392 (6)
C4—C51.361 (7)C14—H140.9300
C4—H40.9300C15—C161.359 (5)
C5—C61.369 (7)C15—H150.9300
C5—H50.9300C16—C171.389 (5)
C6—C71.392 (5)C16—H160.9300
C6—H60.9300C17—N31.372 (4)
C7—N21.406 (5)N1—H10.8600
C8—N51.463 (4)N3—H3A0.8600
C8—H8A0.9700C18—O11.397 (5)
C8—H8B0.9700C18—C191.452 (7)
C9—N51.466 (4)C18—H18A0.9700
C9—C9i1.500 (6)C18—H18B0.9700
C9—H9A0.9700C19—O21.401 (5)
C9—H9B0.9700C19—H19A0.9700
C10—N51.470 (4)C19—H19B0.9700
C10—C111.489 (5)O1—H1A0.8200
C10—H10A0.9700O2—H20.8200
C10—H10B0.9700
N2—C1—N1113.6 (3)C13—C12—N4130.6 (4)
N2—C1—C8122.6 (3)C17—C12—N4108.9 (3)
N1—C1—C8123.8 (3)C14—C13—C12117.4 (4)
N1—C2—C3132.8 (3)C14—C13—H13121.3
N1—C2—C7106.1 (3)C12—C13—H13121.3
C3—C2—C7121.1 (3)C13—C14—C15121.5 (4)
C4—C3—C2116.6 (4)C13—C14—H14119.2
C4—C3—H3121.7C15—C14—H14119.2
C2—C3—H3121.7C16—C15—C14121.4 (4)
C5—C4—C3122.7 (4)C16—C15—H15119.3
C5—C4—H4118.7C14—C15—H15119.3
C3—C4—H4118.7C15—C16—C17117.1 (4)
C4—C5—C6121.5 (4)C15—C16—H16121.4
C4—C5—H5119.2C17—C16—H16121.4
C6—C5—H5119.2N3—C17—C12105.8 (3)
C5—C6—C7117.0 (4)N3—C17—C16132.2 (3)
C5—C6—H6121.5C12—C17—C16122.0 (3)
C7—C6—H6121.5C1—N1—C2106.9 (3)
C2—C7—C6121.1 (4)C1—N1—H1126.5
C2—C7—N2108.8 (3)C2—N1—H1126.5
C6—C7—N2130.1 (4)C1—N2—C7104.5 (3)
N5—C8—C1113.2 (3)C11—N3—C17107.6 (3)
N5—C8—H8A108.9C11—N3—H3A126.2
C1—C8—H8A108.9C17—N3—H3A126.2
N5—C8—H8B108.9C11—N4—C12105.6 (3)
C1—C8—H8B108.9C8—N5—C9111.8 (3)
H8A—C8—H8B107.8C8—N5—C10110.8 (3)
N5—C9—C9i111.0 (3)C9—N5—C10112.5 (3)
N5—C9—H9A109.4O1—C18—C19115.1 (4)
C9i—C9—H9A109.4O1—C18—H18A108.5
N5—C9—H9B109.4C19—C18—H18A108.5
C9i—C9—H9B109.4O1—C18—H18B108.5
H9A—C9—H9B108.0C19—C18—H18B108.5
N5—C10—C11111.1 (3)H18A—C18—H18B107.5
N5—C10—H10A109.4O2—C19—C18113.8 (5)
C11—C10—H10A109.4O2—C19—H19A108.8
N5—C10—H10B109.4C18—C19—H19A108.8
C11—C10—H10B109.4O2—C19—H19B108.8
H10A—C10—H10B108.0C18—C19—H19B108.8
N4—C11—N3112.1 (3)H19A—C19—H19B107.7
N4—C11—C10125.6 (3)C18—O1—H1A109.5
N3—C11—C10122.3 (3)C19—O2—H2109.5
C13—C12—C17120.5 (3)
N1—C2—C3—C4178.0 (4)C15—C16—C17—C120.3 (5)
C7—C2—C3—C41.2 (5)N2—C1—N1—C20.6 (4)
C2—C3—C4—C50.2 (6)C8—C1—N1—C2177.0 (3)
C3—C4—C5—C60.1 (7)C3—C2—N1—C1177.4 (4)
C4—C5—C6—C71.0 (6)C7—C2—N1—C10.3 (3)
N1—C2—C7—C6179.8 (3)N1—C1—N2—C70.7 (4)
C3—C2—C7—C62.2 (5)C8—C1—N2—C7177.0 (3)
N1—C2—C7—N20.1 (3)C2—C7—N2—C10.5 (4)
C3—C2—C7—N2177.4 (3)C6—C7—N2—C1179.9 (4)
C5—C6—C7—C22.0 (6)N4—C11—N3—C170.4 (4)
C5—C6—C7—N2177.5 (4)C10—C11—N3—C17178.1 (3)
N2—C1—C8—N5159.0 (3)C12—C17—N3—C110.6 (3)
N1—C1—C8—N523.6 (5)C16—C17—N3—C11179.5 (4)
N5—C10—C11—N446.1 (5)N3—C11—N4—C120.0 (4)
N5—C10—C11—N3132.1 (3)C10—C11—N4—C12178.4 (3)
C17—C12—C13—C140.0 (6)C13—C12—N4—C11180.0 (4)
N4—C12—C13—C14179.6 (4)C17—C12—N4—C110.4 (4)
C12—C13—C14—C150.7 (7)C1—C8—N5—C9153.4 (3)
C13—C14—C15—C161.4 (7)C1—C8—N5—C1080.2 (4)
C14—C15—C16—C171.1 (6)C9i—C9—N5—C884.1 (4)
C13—C12—C17—N3179.7 (3)C9i—C9—N5—C10150.5 (4)
N4—C12—C17—N30.6 (4)C11—C10—N5—C8173.0 (3)
C13—C12—C17—C160.2 (5)C11—C10—N5—C961.0 (4)
N4—C12—C17—C16179.4 (3)O1—C18—C19—O269.1 (6)
C15—C16—C17—N3179.8 (3)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N4ii0.821.942.734 (4)164
O2—H2···N20.821.892.693 (4)166
N3—H3A···O2iii0.861.932.767 (4)164
N1—H1···O1iv0.861.952.774 (4)160
Symmetry codes: (ii) x, y+1, z; (iii) x+1, y+1, z; (iv) x, y1, z.
 

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