The molecule of the title compound, C
15H
13O
2N
3, deviates slightly from planarity. There is a strong intramolecular N

O hydrogen bond of 2.5831 (19) Å. The molecule exists in the phenol–imine form and the dihedral angle between the two aromatic ring systems is 14.61 (5)°.
Supporting information
CCDC reference: 264071
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.087
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293
PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C7 .. 6.03 su
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
2-(3-Methoxysalicylideneamino)-1
H-benzimidazole
top
Crystal data top
C15H13N3O2 | F(000) = 560 |
Mr = 267.28 | Dx = 1.351 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 17957 reflections |
a = 12.5450 (9) Å | θ = 1.8–26.0° |
b = 8.4858 (8) Å | µ = 0.09 mm−1 |
c = 13.2955 (10) Å | T = 293 K |
β = 111.755 (6)° | Prism, red |
V = 1314.56 (18) Å3 | 0.28 × 0.27 × 0.26 mm |
Z = 4 | |
Data collection top
Stoe IPDS-II diffractometer | 1519 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.072 |
Plane graphite monochromator | θmax = 26.0°, θmin = 1.8° |
Detector resolution: 6.67 pixels mm-1 | h = −15→15 |
φ or ω scans? | k = −10→10 |
23491 measured reflections | l = −16→16 |
2590 independent reflections | |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.88 | w = 1/[σ2(Fo2) + (0.0435P)2] where P = (Fo2 + 2Fc2)/3 |
2590 reflections | (Δ/σ)max < 0.001 |
189 parameters | Δρmax = 0.10 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
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 | Uiso*/Ueq | |
C1 | 0.21604 (14) | 0.2061 (2) | 0.57376 (14) | 0.0435 (4) | |
C2 | 0.32810 (14) | 0.14825 (19) | 0.60831 (13) | 0.0423 (4) | |
C3 | 0.34913 (15) | −0.0010 (2) | 0.57639 (14) | 0.0448 (4) | |
C4 | 0.25974 (16) | −0.0890 (2) | 0.50725 (15) | 0.0540 (5) | |
H4 | 0.2738 | −0.1881 | 0.4851 | 0.065* | |
C5 | 0.14907 (17) | −0.0303 (2) | 0.47070 (16) | 0.0601 (5) | |
H5 | 0.0893 | −0.0896 | 0.4231 | 0.072* | |
C6 | 0.12679 (15) | 0.1140 (2) | 0.50387 (15) | 0.0550 (5) | |
H6 | 0.0518 | 0.1513 | 0.4799 | 0.066* | |
C7 | 0.19215 (14) | 0.3582 (2) | 0.60881 (14) | 0.0481 (4) | |
H7 | 0.1164 | 0.3920 | 0.5871 | 0.058* | |
C8 | 0.24455 (14) | 0.5906 (2) | 0.70480 (14) | 0.0451 (4) | |
C9 | 0.28225 (14) | 0.81828 (19) | 0.78849 (14) | 0.0431 (4) | |
C10 | 0.32800 (16) | 0.9537 (2) | 0.84677 (16) | 0.0554 (5) | |
H10 | 0.4062 | 0.9753 | 0.8715 | 0.066* | |
C11 | 0.25211 (18) | 1.0543 (2) | 0.86612 (17) | 0.0633 (6) | |
H11 | 0.2797 | 1.1463 | 0.9050 | 0.076* | |
C12 | 0.13526 (18) | 1.0226 (2) | 0.82937 (17) | 0.0630 (6) | |
H12 | 0.0868 | 1.0933 | 0.8448 | 0.076* | |
C13 | 0.08975 (16) | 0.8893 (2) | 0.77081 (16) | 0.0559 (5) | |
H13 | 0.0114 | 0.8689 | 0.7463 | 0.067* | |
C14 | 0.16476 (15) | 0.7855 (2) | 0.74927 (14) | 0.0452 (4) | |
C15 | 0.49191 (19) | −0.1851 (2) | 0.57436 (17) | 0.0687 (6) | |
H15A | 0.5725 | −0.2052 | 0.6102 | 0.103* | |
H15B | 0.4745 | −0.1703 | 0.4983 | 0.103* | |
H15C | 0.4490 | −0.2730 | 0.5848 | 0.103* | |
N1 | 0.27272 (12) | 0.44835 (16) | 0.66921 (12) | 0.0478 (4) | |
N2 | 0.33154 (13) | 0.69081 (17) | 0.75866 (12) | 0.0461 (4) | |
N3 | 0.14270 (12) | 0.64128 (17) | 0.69562 (12) | 0.0503 (4) | |
O1 | 0.41963 (10) | 0.23297 (16) | 0.67289 (11) | 0.0546 (4) | |
O2 | 0.46188 (10) | −0.04675 (15) | 0.61838 (10) | 0.0579 (4) | |
H2 | 0.4086 (18) | 0.675 (2) | 0.7739 (16) | 0.071 (6)* | |
H1 | 0.389 (2) | 0.333 (3) | 0.683 (2) | 0.101 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0413 (9) | 0.0434 (9) | 0.0460 (10) | 0.0000 (8) | 0.0165 (8) | −0.0047 (8) |
C2 | 0.0399 (9) | 0.0451 (10) | 0.0400 (9) | −0.0014 (8) | 0.0125 (7) | −0.0047 (8) |
C3 | 0.0456 (10) | 0.0454 (10) | 0.0433 (10) | 0.0068 (8) | 0.0162 (8) | 0.0011 (8) |
C4 | 0.0618 (12) | 0.0459 (10) | 0.0548 (11) | −0.0011 (9) | 0.0220 (10) | −0.0073 (9) |
C5 | 0.0517 (12) | 0.0588 (12) | 0.0643 (13) | −0.0089 (10) | 0.0151 (10) | −0.0164 (10) |
C6 | 0.0390 (10) | 0.0615 (12) | 0.0599 (12) | −0.0027 (9) | 0.0130 (9) | −0.0108 (10) |
C7 | 0.0372 (9) | 0.0518 (10) | 0.0535 (11) | 0.0028 (8) | 0.0146 (8) | −0.0021 (9) |
C8 | 0.0413 (10) | 0.0442 (10) | 0.0484 (10) | 0.0013 (8) | 0.0149 (8) | −0.0038 (8) |
C9 | 0.0461 (10) | 0.0395 (9) | 0.0465 (10) | 0.0014 (8) | 0.0203 (8) | 0.0013 (8) |
C10 | 0.0538 (11) | 0.0495 (11) | 0.0674 (13) | −0.0107 (9) | 0.0278 (10) | −0.0086 (10) |
C11 | 0.0749 (14) | 0.0461 (11) | 0.0773 (14) | −0.0084 (10) | 0.0379 (12) | −0.0146 (10) |
C12 | 0.0680 (13) | 0.0517 (12) | 0.0747 (14) | 0.0092 (10) | 0.0329 (11) | −0.0061 (10) |
C13 | 0.0474 (10) | 0.0558 (12) | 0.0632 (12) | 0.0061 (9) | 0.0192 (9) | −0.0056 (10) |
C14 | 0.0426 (9) | 0.0444 (10) | 0.0463 (10) | 0.0040 (8) | 0.0139 (8) | −0.0004 (8) |
C15 | 0.0760 (14) | 0.0633 (13) | 0.0677 (14) | 0.0244 (11) | 0.0277 (11) | −0.0033 (11) |
N1 | 0.0406 (8) | 0.0450 (8) | 0.0560 (9) | 0.0034 (7) | 0.0159 (7) | −0.0061 (7) |
N2 | 0.0361 (8) | 0.0455 (8) | 0.0563 (9) | −0.0009 (7) | 0.0168 (7) | −0.0039 (7) |
N3 | 0.0392 (8) | 0.0491 (9) | 0.0595 (9) | 0.0012 (7) | 0.0147 (7) | −0.0104 (7) |
O1 | 0.0374 (7) | 0.0529 (8) | 0.0654 (9) | 0.0013 (6) | 0.0096 (6) | −0.0161 (6) |
O2 | 0.0523 (7) | 0.0555 (8) | 0.0595 (8) | 0.0158 (6) | 0.0132 (6) | −0.0079 (6) |
Geometric parameters (Å, º) top
C1—C2 | 1.396 (2) | C9—C10 | 1.386 (2) |
C1—C6 | 1.399 (2) | C9—C14 | 1.397 (2) |
C1—C7 | 1.441 (2) | C10—C11 | 1.372 (3) |
C2—O1 | 1.3571 (19) | C10—H10 | 0.9300 |
C2—C3 | 1.391 (2) | C11—C12 | 1.389 (3) |
C3—O2 | 1.370 (2) | C11—H11 | 0.9300 |
C3—C4 | 1.377 (2) | C12—C13 | 1.372 (3) |
C4—C5 | 1.383 (3) | C12—H12 | 0.9300 |
C4—H4 | 0.9300 | C13—C14 | 1.394 (2) |
C5—C6 | 1.365 (3) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—N3 | 1.391 (2) |
C6—H6 | 0.9300 | C15—O2 | 1.423 (2) |
C7—N1 | 1.285 (2) | C15—H15A | 0.9600 |
C7—H7 | 0.9300 | C15—H15B | 0.9600 |
C8—N3 | 1.310 (2) | C15—H15C | 0.9600 |
C8—N2 | 1.359 (2) | N2—H2 | 0.92 (2) |
C8—N1 | 1.389 (2) | O1—H1 | 0.96 (3) |
C9—N2 | 1.375 (2) | | |
| | | |
C2—C1—C6 | 118.87 (16) | C11—C10—H10 | 121.7 |
C2—C1—C7 | 120.86 (15) | C9—C10—H10 | 121.7 |
C6—C1—C7 | 120.27 (15) | C10—C11—C12 | 121.93 (18) |
O1—C2—C3 | 117.61 (15) | C10—C11—H11 | 119.0 |
O1—C2—C1 | 122.32 (15) | C12—C11—H11 | 119.0 |
C3—C2—C1 | 120.07 (15) | C13—C12—C11 | 121.48 (19) |
O2—C3—C4 | 125.48 (16) | C13—C12—H12 | 119.3 |
O2—C3—C2 | 114.68 (15) | C11—C12—H12 | 119.3 |
C4—C3—C2 | 119.84 (16) | C12—C13—C14 | 117.85 (18) |
C3—C4—C5 | 120.17 (17) | C12—C13—H13 | 121.1 |
C3—C4—H4 | 119.9 | C14—C13—H13 | 121.1 |
C5—C4—H4 | 119.9 | N3—C14—C13 | 129.79 (16) |
C6—C5—C4 | 120.58 (17) | N3—C14—C9 | 110.39 (15) |
C6—C5—H5 | 119.7 | C13—C14—C9 | 119.76 (16) |
C4—C5—H5 | 119.7 | O2—C15—H15A | 109.5 |
C5—C6—C1 | 120.42 (17) | O2—C15—H15B | 109.5 |
C5—C6—H6 | 119.8 | H15A—C15—H15B | 109.5 |
C1—C6—H6 | 119.8 | O2—C15—H15C | 109.5 |
N1—C7—C1 | 121.73 (15) | H15A—C15—H15C | 109.5 |
N1—C7—H7 | 119.1 | H15B—C15—H15C | 109.5 |
C1—C7—H7 | 119.1 | C7—N1—C8 | 119.33 (14) |
N3—C8—N2 | 114.09 (15) | C8—N2—C9 | 106.57 (14) |
N3—C8—N1 | 128.03 (15) | C8—N2—H2 | 126.5 (13) |
N2—C8—N1 | 117.86 (15) | C9—N2—H2 | 126.9 (13) |
N2—C9—C10 | 132.54 (16) | C8—N3—C14 | 103.84 (14) |
N2—C9—C14 | 105.10 (15) | C2—O1—H1 | 105.3 (14) |
C10—C9—C14 | 122.33 (16) | C3—O2—C15 | 117.19 (14) |
C11—C10—C9 | 116.63 (17) | | |
| | | |
C6—C1—C2—O1 | 177.56 (17) | C11—C12—C13—C14 | 0.2 (3) |
C7—C1—C2—O1 | −2.2 (3) | C12—C13—C14—N3 | 177.68 (18) |
C6—C1—C2—C3 | −2.3 (3) | C12—C13—C14—C9 | 0.9 (3) |
C7—C1—C2—C3 | 177.98 (17) | N2—C9—C14—N3 | −0.55 (19) |
O1—C2—C3—O2 | 2.3 (2) | C10—C9—C14—N3 | −178.92 (17) |
C1—C2—C3—O2 | −177.88 (16) | N2—C9—C14—C13 | 176.84 (16) |
O1—C2—C3—C4 | −177.32 (17) | C10—C9—C14—C13 | −1.5 (3) |
C1—C2—C3—C4 | 2.5 (3) | C1—C7—N1—C8 | −176.99 (16) |
O2—C3—C4—C5 | 179.60 (19) | N3—C8—N1—C7 | 8.8 (3) |
C2—C3—C4—C5 | −0.9 (3) | N2—C8—N1—C7 | −173.05 (17) |
C3—C4—C5—C6 | −1.0 (3) | N3—C8—N2—C9 | 0.7 (2) |
C4—C5—C6—C1 | 1.3 (3) | N1—C8—N2—C9 | −177.71 (15) |
C2—C1—C6—C5 | 0.4 (3) | C10—C9—N2—C8 | 178.11 (19) |
C7—C1—C6—C5 | −179.87 (18) | C14—C9—N2—C8 | −0.03 (18) |
C2—C1—C7—N1 | 2.7 (3) | N2—C8—N3—C14 | −1.0 (2) |
C6—C1—C7—N1 | −176.98 (18) | N1—C8—N3—C14 | 177.21 (17) |
N2—C9—C10—C11 | −176.80 (19) | C13—C14—N3—C8 | −176.13 (19) |
C14—C9—C10—C11 | 1.1 (3) | C9—C14—N3—C8 | 0.9 (2) |
C9—C10—C11—C12 | 0.0 (3) | C4—C3—O2—C15 | 10.3 (3) |
C10—C11—C12—C13 | −0.6 (3) | C2—C3—O2—C15 | −169.29 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.96 (3) | 1.71 (3) | 2.5831 (19) | 150 (2) |
C7—H7···N3 | 0.93 | 2.51 | 2.832 (2) | 100 |
N2—H2···O1i | 0.92 (2) | 2.06 (2) | 2.9317 (19) | 156.5 (18) |
N2—H2···O2i | 0.92 (2) | 2.55 (2) | 3.211 (2) | 129.1 (16) |
Symmetry code: (i) −x+1, y+1/2, −z+3/2. |