Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028449/is2176sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028449/is2176Isup2.hkl |
CCDC reference: 654933
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.044
- wR factor = 0.098
- Data-to-parameter ratio = 9.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C6 .. 5.21 su PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.99 From the CIF: _reflns_number_total 1651 Count of symmetry unique reflns 1682 Completeness (_total/calc) 98.16% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A solution of 1,2-benzenediamine (10.8 g, 0.1 mol) and 2-(1-naphthalenyl) acetic acid (18.6 g, 0.1 mol) in ethane-1,2-diol (30 ml) was refluxed for 8 h. After the reaction mixture was cooled to room temperature, it was poured into water (200 ml) and the precipitate was filtered and recrystallized from DMF/ethanol (1:8) to give the title compound, (I), in yield of 83% (m.p. 523 K). Suitable crystals were obtained by vapor diffusion of ethanol and dichloromethane at room temperature.
The N-bound H atom was refined isotropically, with Uiso(H) = 1.2Ueq(N). Other H atoms were treated as riding atoms, with C—H distances 0.93 Å (aromatic) and 0.97 Å (CH2), and with Uiso(H) = 1.2Ueq(C). In the absence of significant anomalous scattering effects, Friedel pairs have been merged.
Benzimidazoles are important heterocycles which exhibite good biological and pharmaceutical activities, such as antitumor activity (Matsuno et al., 2000). Many derivatives of benzimidazole have been prepared and their biological activities were studied (Garuti et al., 1999). In our work of preparing potentially active heterocycles, we obtained the title compound, (I). The benzimidazole ring is planar. The naphthalene ring C1—C10 is twisted with respect to this benzimidazole ring, with a dihedral angle of 78.71 (1)° (Fig. 1). In the crystal structure, intermolecular N—H···N hydrogen bonds form zigzag tapes running along the c axis (Fig. 2 and Table 1). There are no marked π-π interactions.
Many derivatives of benzimidazole have been prepared and their biological and pharmaceutical activities have ben studied by Matsuno et al. (2000) and Garuti et al. (1999).
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: SHELXTL (Sheldrick, 2001).
C18H14N2 | F(000) = 272 |
Mr = 258.31 | Dx = 1.231 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2yc | Cell parameters from 1373 reflections |
a = 8.4578 (16) Å | θ = 2.3–21.6° |
b = 9.0329 (17) Å | µ = 0.07 mm−1 |
c = 9.6474 (18) Å | T = 298 K |
β = 108.932 (3)° | Plate, colorless |
V = 697.2 (2) Å3 | 0.13 × 0.06 × 0.05 mm |
Z = 2 |
Bruker SMART 4K CCD area-detector diffractometer | 1176 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 28.0°, θmin = 2.3° |
φ and ω scans | h = −11→10 |
5884 measured reflections | k = −11→11 |
1651 independent reflections | l = −12→12 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0453P)2] where P = (Fo2 + 2Fc2)/3 |
1651 reflections | (Δ/σ)max < 0.001 |
184 parameters | Δρmax = 0.12 e Å−3 |
2 restraints | Δρmin = −0.10 e Å−3 |
C18H14N2 | V = 697.2 (2) Å3 |
Mr = 258.31 | Z = 2 |
Monoclinic, Pc | Mo Kα radiation |
a = 8.4578 (16) Å | µ = 0.07 mm−1 |
b = 9.0329 (17) Å | T = 298 K |
c = 9.6474 (18) Å | 0.13 × 0.06 × 0.05 mm |
β = 108.932 (3)° |
Bruker SMART 4K CCD area-detector diffractometer | 1176 reflections with I > 2σ(I) |
5884 measured reflections | Rint = 0.035 |
1651 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 2 restraints |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.12 e Å−3 |
1651 reflections | Δρmin = −0.10 e Å−3 |
184 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.5318 (3) | 0.5708 (3) | 0.8424 (3) | 0.0601 (8) | |
H1 | 0.5074 | 0.5024 | 0.9046 | 0.072* | |
C2 | 0.6502 (4) | 0.5376 (4) | 0.7806 (4) | 0.0729 (9) | |
H2 | 0.7065 | 0.4477 | 0.8017 | 0.087* | |
C3 | 0.6881 (4) | 0.6359 (5) | 0.6866 (4) | 0.0806 (10) | |
H3 | 0.7701 | 0.6124 | 0.6452 | 0.097* | |
C4 | 0.6063 (4) | 0.7663 (4) | 0.6546 (4) | 0.0771 (10) | |
H4 | 0.6316 | 0.8311 | 0.5899 | 0.093* | |
C5 | 0.4828 (3) | 0.8063 (4) | 0.7175 (3) | 0.0581 (7) | |
C6 | 0.4001 (5) | 0.9432 (4) | 0.6883 (4) | 0.0820 (10) | |
H6 | 0.4275 | 1.0105 | 0.6268 | 0.098* | |
C7 | 0.2818 (5) | 0.9784 (4) | 0.7480 (5) | 0.0912 (11) | |
H7 | 0.2274 | 1.0691 | 0.7268 | 0.109* | |
C8 | 0.2403 (4) | 0.8782 (4) | 0.8424 (4) | 0.0763 (9) | |
H8 | 0.1569 | 0.9032 | 0.8816 | 0.092* | |
C9 | 0.3195 (3) | 0.7456 (3) | 0.8776 (3) | 0.0535 (7) | |
C10 | 0.4441 (3) | 0.7073 (3) | 0.8147 (3) | 0.0489 (7) | |
C11 | 0.2779 (4) | 0.6426 (3) | 0.9853 (3) | 0.0632 (8) | |
H11A | 0.3815 | 0.6068 | 1.0547 | 0.076* | |
H11B | 0.2202 | 0.6990 | 1.0398 | 0.076* | |
C12 | 0.1730 (3) | 0.5134 (3) | 0.9175 (3) | 0.0489 (7) | |
C13 | 0.0257 (3) | 0.3107 (3) | 0.9082 (3) | 0.0479 (6) | |
C14 | −0.0602 (4) | 0.1883 (3) | 0.9324 (3) | 0.0638 (8) | |
H14 | −0.0532 | 0.1591 | 1.0267 | 0.077* | |
C15 | −0.1564 (4) | 0.1118 (3) | 0.8113 (4) | 0.0731 (9) | |
H15 | −0.2157 | 0.0290 | 0.8237 | 0.088* | |
C16 | −0.1667 (4) | 0.1559 (4) | 0.6702 (4) | 0.0717 (9) | |
H16 | −0.2347 | 0.1030 | 0.5903 | 0.086* | |
C17 | −0.0787 (4) | 0.2758 (3) | 0.6463 (3) | 0.0581 (7) | |
H17 | −0.0845 | 0.3037 | 0.5520 | 0.070* | |
C18 | 0.0192 (3) | 0.3537 (3) | 0.7677 (3) | 0.0452 (6) | |
N1 | 0.1148 (3) | 0.4813 (3) | 0.7772 (2) | 0.0509 (6) | |
N2 | 0.1247 (3) | 0.4135 (3) | 1.0011 (2) | 0.0519 (6) | |
H2A | 0.142 (4) | 0.430 (3) | 1.093 (3) | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0574 (17) | 0.0615 (19) | 0.0588 (18) | 0.0032 (15) | 0.0151 (14) | 0.0005 (14) |
C2 | 0.0534 (18) | 0.077 (2) | 0.088 (2) | 0.0037 (16) | 0.0223 (18) | −0.0165 (19) |
C3 | 0.061 (2) | 0.099 (3) | 0.093 (3) | −0.012 (2) | 0.0403 (19) | −0.023 (2) |
C4 | 0.073 (2) | 0.095 (3) | 0.073 (2) | −0.021 (2) | 0.0381 (18) | −0.0052 (19) |
C5 | 0.0572 (18) | 0.0603 (19) | 0.0554 (17) | −0.0093 (14) | 0.0163 (14) | 0.0017 (13) |
C6 | 0.081 (2) | 0.078 (2) | 0.085 (3) | −0.0061 (19) | 0.024 (2) | 0.0206 (19) |
C7 | 0.089 (3) | 0.059 (2) | 0.117 (3) | 0.019 (2) | 0.021 (2) | 0.019 (2) |
C8 | 0.070 (2) | 0.074 (2) | 0.085 (2) | 0.0127 (18) | 0.0263 (18) | −0.0128 (19) |
C9 | 0.0543 (17) | 0.0585 (18) | 0.0474 (15) | −0.0023 (14) | 0.0160 (13) | −0.0078 (13) |
C10 | 0.0478 (15) | 0.0545 (17) | 0.0416 (15) | −0.0067 (13) | 0.0109 (12) | −0.0058 (12) |
C11 | 0.0685 (19) | 0.083 (2) | 0.0419 (14) | −0.0090 (16) | 0.0234 (13) | −0.0129 (14) |
C12 | 0.0512 (15) | 0.0670 (18) | 0.0332 (14) | 0.0059 (13) | 0.0200 (11) | 0.0005 (13) |
C13 | 0.0496 (15) | 0.0592 (17) | 0.0390 (13) | 0.0084 (13) | 0.0201 (11) | 0.0002 (12) |
C14 | 0.078 (2) | 0.063 (2) | 0.0555 (17) | 0.0067 (16) | 0.0297 (15) | 0.0087 (14) |
C15 | 0.087 (2) | 0.0592 (19) | 0.080 (2) | −0.0094 (18) | 0.0360 (18) | −0.0006 (17) |
C16 | 0.078 (2) | 0.071 (2) | 0.066 (2) | −0.0070 (18) | 0.0233 (16) | −0.0150 (18) |
C17 | 0.0671 (18) | 0.0673 (19) | 0.0415 (15) | 0.0035 (16) | 0.0201 (14) | −0.0034 (13) |
C18 | 0.0467 (14) | 0.0549 (16) | 0.0392 (14) | 0.0094 (13) | 0.0210 (11) | 0.0011 (12) |
N1 | 0.0556 (13) | 0.0660 (15) | 0.0346 (11) | 0.0004 (11) | 0.0196 (9) | −0.0011 (10) |
N2 | 0.0606 (14) | 0.0695 (15) | 0.0291 (10) | 0.0046 (12) | 0.0193 (10) | 0.0032 (11) |
C1—C2 | 1.356 (4) | C11—C12 | 1.484 (4) |
C1—C10 | 1.419 (4) | C11—H11A | 0.9700 |
C1—H1 | 0.9300 | C11—H11B | 0.9700 |
C2—C3 | 1.379 (5) | C12—N1 | 1.314 (3) |
C2—H2 | 0.9300 | C12—N2 | 1.358 (3) |
C3—C4 | 1.350 (5) | C13—N2 | 1.371 (3) |
C3—H3 | 0.9300 | C13—C14 | 1.383 (4) |
C4—C5 | 1.414 (4) | C13—C18 | 1.394 (3) |
C4—H4 | 0.9300 | C14—C15 | 1.374 (4) |
C5—C6 | 1.403 (5) | C14—H14 | 0.9300 |
C5—C10 | 1.409 (4) | C15—C16 | 1.393 (4) |
C6—C7 | 1.344 (5) | C15—H15 | 0.9300 |
C6—H6 | 0.9300 | C16—C17 | 1.375 (4) |
C7—C8 | 1.407 (5) | C16—H16 | 0.9300 |
C7—H7 | 0.9300 | C17—C18 | 1.387 (4) |
C8—C9 | 1.361 (4) | C17—H17 | 0.9300 |
C8—H8 | 0.9300 | C18—N1 | 1.394 (3) |
C9—C10 | 1.418 (4) | N2—H2A | 0.87 (3) |
C9—C11 | 1.519 (4) | ||
C2—C1—C10 | 121.7 (3) | C12—C11—H11A | 108.6 |
C2—C1—H1 | 119.2 | C9—C11—H11A | 108.6 |
C10—C1—H1 | 119.2 | C12—C11—H11B | 108.6 |
C1—C2—C3 | 120.6 (3) | C9—C11—H11B | 108.6 |
C1—C2—H2 | 119.7 | H11A—C11—H11B | 107.6 |
C3—C2—H2 | 119.7 | N1—C12—N2 | 112.4 (2) |
C4—C3—C2 | 120.1 (3) | N1—C12—C11 | 126.7 (2) |
C4—C3—H3 | 120.0 | N2—C12—C11 | 120.9 (2) |
C2—C3—H3 | 120.0 | N2—C13—C14 | 132.4 (2) |
C3—C4—C5 | 121.3 (3) | N2—C13—C18 | 105.6 (2) |
C3—C4—H4 | 119.3 | C14—C13—C18 | 122.0 (3) |
C5—C4—H4 | 119.3 | C15—C14—C13 | 117.2 (3) |
C6—C5—C10 | 119.0 (3) | C15—C14—H14 | 121.4 |
C6—C5—C4 | 121.9 (3) | C13—C14—H14 | 121.4 |
C10—C5—C4 | 119.1 (3) | C14—C15—C16 | 121.3 (3) |
C7—C6—C5 | 120.9 (3) | C14—C15—H15 | 119.3 |
C7—C6—H6 | 119.5 | C16—C15—H15 | 119.3 |
C5—C6—H6 | 119.5 | C17—C16—C15 | 121.5 (3) |
C6—C7—C8 | 120.1 (3) | C17—C16—H16 | 119.3 |
C6—C7—H7 | 119.9 | C15—C16—H16 | 119.3 |
C8—C7—H7 | 119.9 | C16—C17—C18 | 117.7 (3) |
C9—C8—C7 | 121.4 (3) | C16—C17—H17 | 121.1 |
C9—C8—H8 | 119.3 | C18—C17—H17 | 121.1 |
C7—C8—H8 | 119.3 | C17—C18—C13 | 120.3 (2) |
C8—C9—C10 | 118.8 (3) | C17—C18—N1 | 130.5 (2) |
C8—C9—C11 | 120.3 (3) | C13—C18—N1 | 109.2 (2) |
C10—C9—C11 | 120.8 (2) | C12—N1—C18 | 105.4 (2) |
C5—C10—C9 | 119.7 (2) | C12—N2—C13 | 107.4 (2) |
C5—C10—C1 | 117.2 (3) | C12—N2—H2A | 120.6 (18) |
C9—C10—C1 | 123.1 (2) | C13—N2—H2A | 130.8 (19) |
C12—C11—C9 | 114.8 (2) | ||
C10—C1—C2—C3 | −0.7 (5) | C10—C9—C11—C12 | −77.1 (3) |
C1—C2—C3—C4 | −0.4 (5) | C9—C11—C12—N1 | −0.1 (4) |
C2—C3—C4—C5 | 1.0 (5) | C9—C11—C12—N2 | −179.1 (2) |
C3—C4—C5—C6 | 178.2 (3) | N2—C13—C14—C15 | 176.7 (3) |
C3—C4—C5—C10 | −0.4 (5) | C18—C13—C14—C15 | −1.5 (4) |
C10—C5—C6—C7 | −2.1 (5) | C13—C14—C15—C16 | 0.0 (4) |
C4—C5—C6—C7 | 179.3 (3) | C14—C15—C16—C17 | 1.3 (5) |
C5—C6—C7—C8 | 0.6 (6) | C15—C16—C17—C18 | −1.1 (4) |
C6—C7—C8—C9 | 1.1 (5) | C16—C17—C18—C13 | −0.3 (4) |
C7—C8—C9—C10 | −1.3 (4) | C16—C17—C18—N1 | −176.9 (2) |
C7—C8—C9—C11 | 177.2 (3) | N2—C13—C18—C17 | −176.9 (2) |
C6—C5—C10—C9 | 1.9 (4) | C14—C13—C18—C17 | 1.7 (4) |
C4—C5—C10—C9 | −179.5 (3) | N2—C13—C18—N1 | 0.3 (3) |
C6—C5—C10—C1 | −179.4 (3) | C14—C13—C18—N1 | 178.9 (2) |
C4—C5—C10—C1 | −0.7 (4) | N2—C12—N1—C18 | 1.2 (3) |
C8—C9—C10—C5 | −0.2 (4) | C11—C12—N1—C18 | −177.8 (3) |
C11—C9—C10—C5 | −178.7 (2) | C17—C18—N1—C12 | 175.9 (3) |
C8—C9—C10—C1 | −178.9 (3) | C13—C18—N1—C12 | −0.9 (2) |
C11—C9—C10—C1 | 2.6 (4) | N1—C12—N2—C13 | −1.1 (3) |
C2—C1—C10—C5 | 1.3 (4) | C11—C12—N2—C13 | 178.1 (2) |
C2—C1—C10—C9 | 180.0 (3) | C14—C13—N2—C12 | −178.0 (3) |
C8—C9—C11—C12 | 104.5 (3) | C18—C13—N2—C12 | 0.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N1i | 0.87 (3) | 2.03 (3) | 2.855 (3) | 160 (3) |
Symmetry code: (i) x, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H14N2 |
Mr | 258.31 |
Crystal system, space group | Monoclinic, Pc |
Temperature (K) | 298 |
a, b, c (Å) | 8.4578 (16), 9.0329 (17), 9.6474 (18) |
β (°) | 108.932 (3) |
V (Å3) | 697.2 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.13 × 0.06 × 0.05 |
Data collection | |
Diffractometer | Bruker SMART 4K CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5884, 1651, 1176 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.660 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.098, 1.03 |
No. of reflections | 1651 |
No. of parameters | 184 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.12, −0.10 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N1i | 0.87 (3) | 2.03 (3) | 2.855 (3) | 160 (3) |
Symmetry code: (i) x, −y+1, z+1/2. |
Benzimidazoles are important heterocycles which exhibite good biological and pharmaceutical activities, such as antitumor activity (Matsuno et al., 2000). Many derivatives of benzimidazole have been prepared and their biological activities were studied (Garuti et al., 1999). In our work of preparing potentially active heterocycles, we obtained the title compound, (I). The benzimidazole ring is planar. The naphthalene ring C1—C10 is twisted with respect to this benzimidazole ring, with a dihedral angle of 78.71 (1)° (Fig. 1). In the crystal structure, intermolecular N—H···N hydrogen bonds form zigzag tapes running along the c axis (Fig. 2 and Table 1). There are no marked π-π interactions.