Buy article online - an online subscription or single-article purchase is required to access this article.
The title compound, C
26H
26N
4·2CH
3OH, 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 (
01).
Supporting information
CCDC reference: 262473
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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
C26H26N4·2CH4O | F(000) = 492 |
Mr = 458.59 | Dx = 1.27 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5358 reflections |
a = 5.2957 (3) Å | θ = 2.9–25.1° |
b = 16.2732 (9) Å | µ = 0.08 mm−1 |
c = 13.9411 (8) Å | T = 150 K |
β = 93.200 (1)° | Block, colourless |
V = 1199.54 (12) Å3 | 0.42 × 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 scans | Rint = 0.048 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 25.1°, θmin = 1.9° |
Tmin = 0.967, Tmax = 0.993 | h = −6→6 |
8425 measured reflections | k = −19→19 |
2118 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 1.08 | Δρmax = 0.17 e Å−3 |
2118 reflections | Δρmin = −0.16 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.3629 (3) | 0.28364 (9) | 0.34899 (11) | 0.0306 (4) | |
H1 | 0.471 (3) | 0.2759 (9) | 0.4062 (11) | 0.030 (4)* | |
C2 | 0.0769 (3) | 0.26580 (9) | 0.23679 (11) | 0.0306 (4) | |
C3 | −0.1200 (3) | 0.23692 (11) | 0.17508 (12) | 0.0398 (4) | |
H3 | −0.198 (4) | 0.1849 (12) | 0.1863 (13) | 0.050 (5)* | |
C4 | −0.2008 (3) | 0.28647 (11) | 0.09980 (13) | 0.0422 (4) | |
H4 | −0.339 (3) | 0.2691 (10) | 0.0567 (12) | 0.041 (5)* | |
C5 | −0.0887 (3) | 0.36314 (11) | 0.08408 (12) | 0.0385 (4) | |
H5 | −0.150 (3) | 0.3952 (11) | 0.0306 (13) | 0.044 (5)* | |
C6 | 0.1068 (3) | 0.39287 (10) | 0.14398 (11) | 0.0318 (4) | |
H6 | 0.187 (3) | 0.4441 (10) | 0.1315 (11) | 0.032 (4)* | |
C7 | 0.1847 (3) | 0.34290 (9) | 0.22105 (10) | 0.0271 (3) | |
C8 | 0.5375 (3) | 0.42416 (9) | 0.31131 (10) | 0.0261 (3) | |
H8A | 0.489 (3) | 0.4637 (9) | 0.2590 (11) | 0.027 (4)* | |
H8B | 0.711 (3) | 0.4058 (9) | 0.3040 (10) | 0.023 (4)* | |
C9 | 0.5167 (3) | 0.46255 (8) | 0.40979 (10) | 0.0237 (3) | |
C10 | 0.6798 (3) | 0.43798 (8) | 0.48747 (10) | 0.0242 (3) | |
C11 | 0.6647 (2) | 0.47602 (8) | 0.57738 (10) | 0.0240 (3) | |
C12 | 0.8719 (3) | 0.37020 (10) | 0.47863 (12) | 0.0309 (4) | |
H12A | 1.044 (4) | 0.3903 (10) | 0.4961 (12) | 0.040 (4)* | |
H12B | 0.868 (3) | 0.3444 (11) | 0.4145 (13) | 0.045 (5)* | |
H12C | 0.837 (3) | 0.3249 (11) | 0.5243 (13) | 0.047 (5)* | |
C13 | 0.8504 (3) | 0.45006 (10) | 0.65803 (11) | 0.0301 (4) | |
H13A | 1.026 (4) | 0.4531 (11) | 0.6382 (13) | 0.047 (5)* | |
H13B | 0.822 (3) | 0.3932 (12) | 0.6773 (13) | 0.050 (5)* | |
H13C | 0.844 (4) | 0.4851 (13) | 0.7166 (15) | 0.055 (5)* | |
N1 | 0.3681 (2) | 0.35296 (7) | 0.29526 (8) | 0.0261 (3) | |
N2 | 0.1944 (3) | 0.22967 (7) | 0.31778 (9) | 0.0352 (3) | |
C14 | −0.1718 (4) | 0.08336 (12) | 0.40694 (16) | 0.0562 (5) | |
H1A | −0.2084 | 0.0373 | 0.4493 | 0.104 (9)* | |
H1B | −0.3052 | 0.0875 | 0.3555 | 0.133 (12)* | |
H1C | −0.1648 | 0.1345 | 0.4442 | 0.092 (8)* | |
O1 | 0.0616 (2) | 0.07026 (7) | 0.36669 (9) | 0.0444 (3) | |
H1D | 0.124 (4) | 0.1204 (14) | 0.3506 (15) | 0.067 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0356 (8) | 0.0245 (8) | 0.0315 (8) | 0.0008 (6) | 0.0011 (7) | −0.0007 (6) |
C2 | 0.0327 (8) | 0.0249 (8) | 0.0348 (8) | −0.0014 (6) | 0.0058 (6) | −0.0055 (6) |
C3 | 0.0411 (9) | 0.0323 (9) | 0.0458 (10) | −0.0103 (7) | 0.0025 (7) | −0.0084 (7) |
C4 | 0.0368 (9) | 0.0453 (10) | 0.0436 (10) | −0.0082 (8) | −0.0053 (8) | −0.0112 (8) |
C5 | 0.0421 (9) | 0.0403 (9) | 0.0325 (8) | −0.0020 (8) | −0.0049 (7) | −0.0029 (7) |
C6 | 0.0366 (8) | 0.0294 (8) | 0.0297 (8) | −0.0042 (7) | 0.0033 (6) | −0.0025 (6) |
C7 | 0.0270 (7) | 0.0259 (8) | 0.0288 (7) | −0.0015 (6) | 0.0047 (6) | −0.0073 (6) |
C8 | 0.0249 (8) | 0.0250 (7) | 0.0286 (8) | −0.0029 (6) | 0.0026 (6) | −0.0028 (6) |
C9 | 0.0235 (7) | 0.0201 (7) | 0.0274 (7) | −0.0042 (5) | 0.0024 (5) | −0.0007 (5) |
C10 | 0.0229 (7) | 0.0198 (7) | 0.0301 (7) | −0.0021 (5) | 0.0038 (6) | −0.0002 (5) |
C11 | 0.0232 (7) | 0.0207 (7) | 0.0280 (7) | −0.0031 (6) | 0.0008 (5) | 0.0020 (5) |
C12 | 0.0284 (8) | 0.0279 (8) | 0.0363 (9) | 0.0048 (6) | 0.0010 (6) | −0.0036 (7) |
C13 | 0.0299 (8) | 0.0292 (8) | 0.0308 (8) | 0.0028 (6) | −0.0017 (6) | 0.0013 (7) |
N1 | 0.0280 (6) | 0.0230 (6) | 0.0274 (6) | −0.0020 (5) | 0.0027 (5) | −0.0024 (5) |
N2 | 0.0402 (7) | 0.0242 (7) | 0.0412 (8) | −0.0030 (6) | 0.0025 (6) | −0.0005 (5) |
C14 | 0.0557 (12) | 0.0478 (12) | 0.0669 (13) | −0.0071 (9) | 0.0191 (10) | 0.0016 (10) |
O1 | 0.0568 (8) | 0.0260 (6) | 0.0517 (7) | −0.0005 (5) | 0.0167 (6) | 0.0003 (5) |
Geometric parameters (Å, º) top
C1—N2 | 1.3087 (19) | C8—H8B | 0.979 (16) |
C1—N1 | 1.3553 (19) | C9—C11i | 1.405 (2) |
C1—H1 | 0.963 (15) | C9—C10 | 1.4049 (19) |
C2—N2 | 1.3891 (19) | C10—C11 | 1.404 (2) |
C2—C3 | 1.396 (2) | C10—C12 | 1.510 (2) |
C2—C7 | 1.401 (2) | C11—C9i | 1.405 (2) |
C3—C4 | 1.373 (2) | C11—C13 | 1.5121 (19) |
C3—H3 | 0.959 (19) | C12—H12A | 0.986 (19) |
C4—C5 | 1.404 (2) | C12—H12B | 0.987 (19) |
C4—H4 | 0.962 (17) | C12—H12C | 0.997 (19) |
C5—C6 | 1.381 (2) | C13—H13A | 0.99 (2) |
C5—H5 | 0.953 (18) | C13—H13B | 0.978 (19) |
C6—C7 | 1.392 (2) | C13—H13C | 1.00 (2) |
C6—H6 | 0.956 (17) | C14—O1 | 1.402 (2) |
C7—N1 | 1.3884 (18) | C14—H1A | 0.98 |
C8—N1 | 1.4749 (17) | C14—H1B | 0.98 |
C8—C9 | 1.5180 (19) | C14—H1C | 0.98 |
C8—H8A | 0.994 (15) | O1—H1D | 0.91 (2) |
| | | |
N2—C1—N1 | 114.17 (13) | C11—C10—C9 | 119.96 (13) |
N2—C1—H1 | 123.3 (9) | C11—C10—C12 | 117.84 (12) |
N1—C1—H1 | 122.5 (9) | C9—C10—C12 | 122.19 (13) |
N2—C2—C3 | 130.10 (14) | C10—C11—C9i | 120.05 (12) |
N2—C2—C7 | 109.77 (12) | C10—C11—C13 | 118.26 (13) |
C3—C2—C7 | 120.13 (14) | C9i—C11—C13 | 121.68 (13) |
C4—C3—C2 | 117.63 (15) | C10—C12—H12A | 110.8 (10) |
C4—C3—H3 | 121.6 (11) | C10—C12—H12B | 113.9 (10) |
C2—C3—H3 | 120.7 (11) | H12A—C12—H12B | 109.7 (15) |
C3—C4—C5 | 121.65 (15) | C10—C12—H12C | 109.7 (11) |
C3—C4—H4 | 119.9 (10) | H12A—C12—H12C | 106.8 (14) |
C5—C4—H4 | 118.5 (10) | H12B—C12—H12C | 105.6 (14) |
C6—C5—C4 | 121.74 (16) | C11—C13—H13A | 111.2 (10) |
C6—C5—H5 | 119.6 (11) | C11—C13—H13B | 111.4 (11) |
C4—C5—H5 | 118.6 (11) | H13A—C13—H13B | 106.6 (15) |
C5—C6—C7 | 116.26 (15) | C11—C13—H13C | 113.6 (11) |
C5—C6—H6 | 121.4 (9) | H13A—C13—H13C | 106.0 (15) |
C7—C6—H6 | 122.3 (9) | H13B—C13—H13C | 107.6 (16) |
N1—C7—C6 | 132.18 (13) | C1—N1—C7 | 106.18 (12) |
N1—C7—C2 | 105.26 (12) | C1—N1—C8 | 126.95 (12) |
C6—C7—C2 | 122.57 (13) | C7—N1—C8 | 126.86 (12) |
N1—C8—C9 | 112.72 (11) | C1—N2—C2 | 104.62 (12) |
N1—C8—H8A | 105.6 (8) | O1—C14—H1A | 109.5 |
C9—C8—H8A | 111.6 (9) | O1—C14—H1B | 109.5 |
N1—C8—H8B | 108.2 (8) | H1A—C14—H1B | 109.5 |
C9—C8—H8B | 109.6 (9) | O1—C14—H1C | 109.5 |
H8A—C8—H8B | 109.0 (12) | H1A—C14—H1C | 109.5 |
C11i—C9—C10 | 119.98 (13) | H1B—C14—H1C | 109.5 |
C11i—C9—C8 | 119.51 (12) | C14—O1—H1D | 107.6 (14) |
C10—C9—C8 | 120.50 (12) | | |
| | | |
N2—C2—C3—C4 | 179.67 (16) | C8—C9—C10—C12 | −3.2 (2) |
C7—C2—C3—C4 | 0.1 (2) | C9—C10—C11—C9i | 1.3 (2) |
C2—C3—C4—C5 | 0.8 (3) | C12—C10—C11—C9i | −177.81 (13) |
C3—C4—C5—C6 | −0.6 (3) | C9—C10—C11—C13 | −177.67 (12) |
C4—C5—C6—C7 | −0.5 (2) | C12—C10—C11—C13 | 3.2 (2) |
C5—C6—C7—N1 | −178.74 (15) | N2—C1—N1—C7 | −0.33 (17) |
C5—C6—C7—C2 | 1.4 (2) | N2—C1—N1—C8 | −179.31 (13) |
N2—C2—C7—N1 | −0.78 (16) | C6—C7—N1—C1 | −179.23 (16) |
C3—C2—C7—N1 | 178.85 (14) | C2—C7—N1—C1 | 0.66 (15) |
N2—C2—C7—C6 | 179.13 (13) | C6—C7—N1—C8 | −0.3 (2) |
C3—C2—C7—C6 | −1.3 (2) | C2—C7—N1—C8 | 179.64 (13) |
N1—C8—C9—C11i | −88.11 (15) | C9—C8—N1—C1 | −57.68 (18) |
N1—C8—C9—C10 | 92.89 (15) | C9—C8—N1—C7 | 123.55 (14) |
C11i—C9—C10—C11 | −1.3 (2) | N1—C1—N2—C2 | −0.15 (18) |
C8—C9—C10—C11 | 177.73 (12) | C3—C2—N2—C1 | −178.99 (16) |
C11i—C9—C10—C12 | 177.77 (13) | C7—C2—N2—C1 | 0.58 (17) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1D···N2 | 0.91 (2) | 1.88 (2) | 2.783 (2) | 170 (2) |
C6—H6···O1ii | 0.96 (2) | 2.45 (2) | 3.386 (2) | 168 (1) |
C8—H8A···O1ii | 1.00 (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.