Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C26H26N4·2CH3OH, lies across a crystallographic inversion centre. The two benzimidazole pendant substituents adopt a trans conformation. O—H...N and C—H...O hydrogen bonds link the molecules into a two-dimensional network parallel to (\overline101).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032684/ci6495sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032684/ci6495Isup2.hkl
Contains datablock I

CCDC reference: 262473

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.103
  • Data-to-parameter ratio = 9.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.90
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 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, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

1,4-Bis(benzimidazol-1-ylmethyl)-2,3,5,6-tetramethylbenzene methanol disolvate top
Crystal data top
C26H26N4·2CH4OF(000) = 492
Mr = 458.59Dx = 1.27 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5358 reflections
a = 5.2957 (3) Åθ = 2.9–25.1°
b = 16.2732 (9) ŵ = 0.08 mm1
c = 13.9411 (8) ÅT = 150 K
β = 93.200 (1)°Block, colourless
V = 1199.54 (12) Å30.42 × 0.20 × 0.12 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
1903 reflections with I > 2σ(I)
φ and ω scansRint = 0.048
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
θmax = 25.1°, θmin = 1.9°
Tmin = 0.967, Tmax = 0.993h = 66
8425 measured reflectionsk = 1919
2118 independent reflectionsl = 1616
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.0504P)2 + 0.2602P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.103(Δ/σ)max = 0.002
S = 1.08Δρmax = 0.17 e Å3
2118 reflectionsΔρmin = 0.16 e Å3
214 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3629 (3)0.28364 (9)0.34899 (11)0.0306 (4)
H10.471 (3)0.2759 (9)0.4062 (11)0.030 (4)*
C20.0769 (3)0.26580 (9)0.23679 (11)0.0306 (4)
C30.1200 (3)0.23692 (11)0.17508 (12)0.0398 (4)
H30.198 (4)0.1849 (12)0.1863 (13)0.050 (5)*
C40.2008 (3)0.28647 (11)0.09980 (13)0.0422 (4)
H40.339 (3)0.2691 (10)0.0567 (12)0.041 (5)*
C50.0887 (3)0.36314 (11)0.08408 (12)0.0385 (4)
H50.150 (3)0.3952 (11)0.0306 (13)0.044 (5)*
C60.1068 (3)0.39287 (10)0.14398 (11)0.0318 (4)
H60.187 (3)0.4441 (10)0.1315 (11)0.032 (4)*
C70.1847 (3)0.34290 (9)0.22105 (10)0.0271 (3)
C80.5375 (3)0.42416 (9)0.31131 (10)0.0261 (3)
H8A0.489 (3)0.4637 (9)0.2590 (11)0.027 (4)*
H8B0.711 (3)0.4058 (9)0.3040 (10)0.023 (4)*
C90.5167 (3)0.46255 (8)0.40979 (10)0.0237 (3)
C100.6798 (3)0.43798 (8)0.48747 (10)0.0242 (3)
C110.6647 (2)0.47602 (8)0.57738 (10)0.0240 (3)
C120.8719 (3)0.37020 (10)0.47863 (12)0.0309 (4)
H12A1.044 (4)0.3903 (10)0.4961 (12)0.040 (4)*
H12B0.868 (3)0.3444 (11)0.4145 (13)0.045 (5)*
H12C0.837 (3)0.3249 (11)0.5243 (13)0.047 (5)*
C130.8504 (3)0.45006 (10)0.65803 (11)0.0301 (4)
H13A1.026 (4)0.4531 (11)0.6382 (13)0.047 (5)*
H13B0.822 (3)0.3932 (12)0.6773 (13)0.050 (5)*
H13C0.844 (4)0.4851 (13)0.7166 (15)0.055 (5)*
N10.3681 (2)0.35296 (7)0.29526 (8)0.0261 (3)
N20.1944 (3)0.22967 (7)0.31778 (9)0.0352 (3)
C140.1718 (4)0.08336 (12)0.40694 (16)0.0562 (5)
H1A0.20840.03730.44930.104 (9)*
H1B0.30520.08750.35550.133 (12)*
H1C0.16480.13450.44420.092 (8)*
O10.0616 (2)0.07026 (7)0.36669 (9)0.0444 (3)
H1D0.124 (4)0.1204 (14)0.3506 (15)0.067 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0356 (8)0.0245 (8)0.0315 (8)0.0008 (6)0.0011 (7)0.0007 (6)
C20.0327 (8)0.0249 (8)0.0348 (8)0.0014 (6)0.0058 (6)0.0055 (6)
C30.0411 (9)0.0323 (9)0.0458 (10)0.0103 (7)0.0025 (7)0.0084 (7)
C40.0368 (9)0.0453 (10)0.0436 (10)0.0082 (8)0.0053 (8)0.0112 (8)
C50.0421 (9)0.0403 (9)0.0325 (8)0.0020 (8)0.0049 (7)0.0029 (7)
C60.0366 (8)0.0294 (8)0.0297 (8)0.0042 (7)0.0033 (6)0.0025 (6)
C70.0270 (7)0.0259 (8)0.0288 (7)0.0015 (6)0.0047 (6)0.0073 (6)
C80.0249 (8)0.0250 (7)0.0286 (8)0.0029 (6)0.0026 (6)0.0028 (6)
C90.0235 (7)0.0201 (7)0.0274 (7)0.0042 (5)0.0024 (5)0.0007 (5)
C100.0229 (7)0.0198 (7)0.0301 (7)0.0021 (5)0.0038 (6)0.0002 (5)
C110.0232 (7)0.0207 (7)0.0280 (7)0.0031 (6)0.0008 (5)0.0020 (5)
C120.0284 (8)0.0279 (8)0.0363 (9)0.0048 (6)0.0010 (6)0.0036 (7)
C130.0299 (8)0.0292 (8)0.0308 (8)0.0028 (6)0.0017 (6)0.0013 (7)
N10.0280 (6)0.0230 (6)0.0274 (6)0.0020 (5)0.0027 (5)0.0024 (5)
N20.0402 (7)0.0242 (7)0.0412 (8)0.0030 (6)0.0025 (6)0.0005 (5)
C140.0557 (12)0.0478 (12)0.0669 (13)0.0071 (9)0.0191 (10)0.0016 (10)
O10.0568 (8)0.0260 (6)0.0517 (7)0.0005 (5)0.0167 (6)0.0003 (5)
Geometric parameters (Å, º) top
C1—N21.3087 (19)C8—H8B0.979 (16)
C1—N11.3553 (19)C9—C11i1.405 (2)
C1—H10.963 (15)C9—C101.4049 (19)
C2—N21.3891 (19)C10—C111.404 (2)
C2—C31.396 (2)C10—C121.510 (2)
C2—C71.401 (2)C11—C9i1.405 (2)
C3—C41.373 (2)C11—C131.5121 (19)
C3—H30.959 (19)C12—H12A0.986 (19)
C4—C51.404 (2)C12—H12B0.987 (19)
C4—H40.962 (17)C12—H12C0.997 (19)
C5—C61.381 (2)C13—H13A0.99 (2)
C5—H50.953 (18)C13—H13B0.978 (19)
C6—C71.392 (2)C13—H13C1.00 (2)
C6—H60.956 (17)C14—O11.402 (2)
C7—N11.3884 (18)C14—H1A0.98
C8—N11.4749 (17)C14—H1B0.98
C8—C91.5180 (19)C14—H1C0.98
C8—H8A0.994 (15)O1—H1D0.91 (2)
N2—C1—N1114.17 (13)C11—C10—C9119.96 (13)
N2—C1—H1123.3 (9)C11—C10—C12117.84 (12)
N1—C1—H1122.5 (9)C9—C10—C12122.19 (13)
N2—C2—C3130.10 (14)C10—C11—C9i120.05 (12)
N2—C2—C7109.77 (12)C10—C11—C13118.26 (13)
C3—C2—C7120.13 (14)C9i—C11—C13121.68 (13)
C4—C3—C2117.63 (15)C10—C12—H12A110.8 (10)
C4—C3—H3121.6 (11)C10—C12—H12B113.9 (10)
C2—C3—H3120.7 (11)H12A—C12—H12B109.7 (15)
C3—C4—C5121.65 (15)C10—C12—H12C109.7 (11)
C3—C4—H4119.9 (10)H12A—C12—H12C106.8 (14)
C5—C4—H4118.5 (10)H12B—C12—H12C105.6 (14)
C6—C5—C4121.74 (16)C11—C13—H13A111.2 (10)
C6—C5—H5119.6 (11)C11—C13—H13B111.4 (11)
C4—C5—H5118.6 (11)H13A—C13—H13B106.6 (15)
C5—C6—C7116.26 (15)C11—C13—H13C113.6 (11)
C5—C6—H6121.4 (9)H13A—C13—H13C106.0 (15)
C7—C6—H6122.3 (9)H13B—C13—H13C107.6 (16)
N1—C7—C6132.18 (13)C1—N1—C7106.18 (12)
N1—C7—C2105.26 (12)C1—N1—C8126.95 (12)
C6—C7—C2122.57 (13)C7—N1—C8126.86 (12)
N1—C8—C9112.72 (11)C1—N2—C2104.62 (12)
N1—C8—H8A105.6 (8)O1—C14—H1A109.5
C9—C8—H8A111.6 (9)O1—C14—H1B109.5
N1—C8—H8B108.2 (8)H1A—C14—H1B109.5
C9—C8—H8B109.6 (9)O1—C14—H1C109.5
H8A—C8—H8B109.0 (12)H1A—C14—H1C109.5
C11i—C9—C10119.98 (13)H1B—C14—H1C109.5
C11i—C9—C8119.51 (12)C14—O1—H1D107.6 (14)
C10—C9—C8120.50 (12)
N2—C2—C3—C4179.67 (16)C8—C9—C10—C123.2 (2)
C7—C2—C3—C40.1 (2)C9—C10—C11—C9i1.3 (2)
C2—C3—C4—C50.8 (3)C12—C10—C11—C9i177.81 (13)
C3—C4—C5—C60.6 (3)C9—C10—C11—C13177.67 (12)
C4—C5—C6—C70.5 (2)C12—C10—C11—C133.2 (2)
C5—C6—C7—N1178.74 (15)N2—C1—N1—C70.33 (17)
C5—C6—C7—C21.4 (2)N2—C1—N1—C8179.31 (13)
N2—C2—C7—N10.78 (16)C6—C7—N1—C1179.23 (16)
C3—C2—C7—N1178.85 (14)C2—C7—N1—C10.66 (15)
N2—C2—C7—C6179.13 (13)C6—C7—N1—C80.3 (2)
C3—C2—C7—C61.3 (2)C2—C7—N1—C8179.64 (13)
N1—C8—C9—C11i88.11 (15)C9—C8—N1—C157.68 (18)
N1—C8—C9—C1092.89 (15)C9—C8—N1—C7123.55 (14)
C11i—C9—C10—C111.3 (2)N1—C1—N2—C20.15 (18)
C8—C9—C10—C11177.73 (12)C3—C2—N2—C1178.99 (16)
C11i—C9—C10—C12177.77 (13)C7—C2—N2—C10.58 (17)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1D···N20.91 (2)1.88 (2)2.783 (2)170 (2)
C6—H6···O1ii0.96 (2)2.45 (2)3.386 (2)168 (1)
C8—H8A···O1ii1.00 (2)2.47 (2)3.456 (2)171 (1)
Symmetry code: (ii) x+1/2, y+1/2, z+1/2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

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

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds