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In the title compound, C
18H
16N
4, the two imidazole rings are twisted away from the central naphthalene ring system by 81.4 (1) and 88.4 (1)°. The crystal packing is stabilized by C—H
N hydrogen bonds
Supporting information
CCDC reference: 289700
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.108
- Data-to-parameter ratio = 9.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.76
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.64 Ratio
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 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
4 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989); 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: SHELXL97.
1,4-Bis(imidazol-1-ylmethyl)naphthalene
top
Crystal data top
C18H16N4 | F(000) = 608 |
Mr = 288.35 | Dx = 1.314 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 20 reflections |
a = 8.222 (4) Å | θ = 4.5–7.4° |
b = 19.541 (8) Å | µ = 0.08 mm−1 |
c = 9.956 (3) Å | T = 293 K |
β = 114.31 (3)° | Block, colourless |
V = 1457.8 (10) Å3 | 0.28 × 0.22 × 0.18 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.047 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.1° |
Graphite monochromator | h = −9→8 |
ω/2θ scans | k = 0→23 |
2664 measured reflections | l = 0→11 |
2568 independent reflections | 3 standard reflections every 300 reflections |
1157 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | All H-atom parameters refined |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0454P)2] where P = (Fo2 + 2Fc2)/3 |
2568 reflections | (Δ/σ)max = 0.001 |
263 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.16 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 | |
N1 | 0.5776 (3) | 0.70133 (11) | 0.1311 (2) | 0.0456 (6) | |
N2 | 0.7139 (4) | 0.68164 (14) | −0.0144 (3) | 0.0719 (8) | |
N3 | 0.9207 (3) | 0.53278 (11) | 0.8107 (2) | 0.0499 (6) | |
N4 | 1.1991 (4) | 0.56693 (15) | 0.9338 (3) | 0.0734 (8) | |
C1 | 0.5171 (3) | 0.64973 (13) | 0.3338 (2) | 0.0404 (6) | |
C2 | 0.2501 (4) | 0.67878 (15) | 0.3780 (3) | 0.0525 (7) | |
C3 | 0.1522 (4) | 0.67338 (17) | 0.4600 (3) | 0.0618 (8) | |
C4 | 0.2133 (4) | 0.63341 (17) | 0.5867 (3) | 0.0608 (8) | |
C5 | 0.3727 (4) | 0.60072 (15) | 0.6325 (3) | 0.0520 (8) | |
C6 | 0.6504 (3) | 0.57283 (13) | 0.5989 (3) | 0.0441 (7) | |
C7 | 0.7393 (4) | 0.57648 (14) | 0.5104 (3) | 0.0480 (7) | |
C8 | 0.6738 (4) | 0.61457 (14) | 0.3793 (3) | 0.0457 (7) | |
C9 | 0.4158 (3) | 0.64498 (13) | 0.4197 (2) | 0.0396 (6) | |
C10 | 0.4798 (3) | 0.60527 (13) | 0.5516 (2) | 0.0418 (6) | |
C11 | 0.4501 (4) | 0.69349 (16) | 0.1971 (3) | 0.0501 (7) | |
C12 | 0.5789 (5) | 0.66531 (17) | 0.0164 (3) | 0.0615 (8) | |
C13 | 0.8019 (5) | 0.73085 (19) | 0.0869 (4) | 0.0655 (9) | |
C14 | 0.7206 (4) | 0.74427 (17) | 0.1771 (3) | 0.0544 (8) | |
C15 | 0.7258 (4) | 0.53583 (19) | 0.7452 (3) | 0.0586 (8) | |
C16 | 1.0281 (5) | 0.48271 (17) | 0.7961 (3) | 0.0646 (9) | |
C17 | 1.1968 (5) | 0.5048 (2) | 0.8720 (4) | 0.0698 (10) | |
C18 | 1.0299 (5) | 0.58145 (18) | 0.8942 (3) | 0.0645 (9) | |
H2 | 0.210 (3) | 0.7073 (10) | 0.287 (2) | 0.035 (6)* | |
H3 | 0.037 (4) | 0.6969 (13) | 0.427 (3) | 0.074 (9)* | |
H4 | 0.140 (3) | 0.6298 (12) | 0.642 (3) | 0.059 (8)* | |
H5 | 0.417 (3) | 0.5698 (13) | 0.719 (3) | 0.064 (8)* | |
H7 | 0.851 (3) | 0.5543 (12) | 0.535 (3) | 0.057 (8)* | |
H8 | 0.743 (3) | 0.6158 (10) | 0.323 (2) | 0.031 (6)* | |
H111 | 0.329 (3) | 0.6744 (11) | 0.125 (3) | 0.058 (8)* | |
H112 | 0.423 (3) | 0.7414 (12) | 0.220 (3) | 0.052 (8)* | |
H12 | 0.481 (4) | 0.6314 (16) | −0.036 (3) | 0.100 (12)* | |
H13 | 0.897 (4) | 0.7530 (14) | 0.091 (3) | 0.074 (10)* | |
H14 | 0.748 (4) | 0.7731 (15) | 0.261 (3) | 0.087 (11)* | |
H151 | 0.685 (3) | 0.4895 (14) | 0.734 (3) | 0.056 (9)* | |
H152 | 0.694 (3) | 0.5611 (12) | 0.820 (3) | 0.060 (8)* | |
H16 | 0.975 (4) | 0.4428 (16) | 0.732 (4) | 0.105 (12)* | |
H17 | 1.298 (5) | 0.4803 (17) | 0.886 (4) | 0.113 (14)* | |
H18 | 0.981 (3) | 0.6224 (14) | 0.920 (3) | 0.071 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0518 (15) | 0.0510 (14) | 0.0345 (12) | 0.0055 (12) | 0.0183 (10) | 0.0052 (10) |
N2 | 0.093 (2) | 0.0763 (19) | 0.0626 (17) | 0.0123 (17) | 0.0481 (16) | 0.0089 (15) |
N3 | 0.0571 (16) | 0.0482 (14) | 0.0427 (13) | 0.0009 (14) | 0.0187 (12) | 0.0040 (11) |
N4 | 0.0611 (19) | 0.086 (2) | 0.0649 (17) | −0.0055 (17) | 0.0180 (14) | 0.0046 (16) |
C1 | 0.0389 (15) | 0.0483 (16) | 0.0341 (14) | −0.0040 (13) | 0.0151 (12) | −0.0040 (12) |
C2 | 0.0434 (18) | 0.066 (2) | 0.0457 (17) | 0.0017 (15) | 0.0163 (14) | −0.0009 (15) |
C3 | 0.0462 (19) | 0.084 (2) | 0.0570 (19) | 0.0006 (18) | 0.0233 (16) | −0.0076 (17) |
C4 | 0.047 (2) | 0.087 (2) | 0.057 (2) | −0.0097 (18) | 0.0300 (17) | −0.0117 (17) |
C5 | 0.052 (2) | 0.065 (2) | 0.0425 (17) | −0.0095 (16) | 0.0229 (15) | −0.0041 (15) |
C6 | 0.0479 (17) | 0.0431 (16) | 0.0400 (15) | −0.0079 (14) | 0.0168 (13) | 0.0017 (12) |
C7 | 0.0497 (18) | 0.0519 (18) | 0.0440 (16) | 0.0072 (15) | 0.0207 (14) | 0.0068 (14) |
C8 | 0.0471 (18) | 0.0557 (18) | 0.0407 (16) | −0.0008 (15) | 0.0246 (14) | −0.0006 (13) |
C9 | 0.0342 (15) | 0.0469 (16) | 0.0357 (14) | −0.0022 (13) | 0.0125 (12) | −0.0054 (12) |
C10 | 0.0408 (16) | 0.0480 (16) | 0.0374 (15) | −0.0092 (13) | 0.0169 (13) | −0.0081 (12) |
C11 | 0.0465 (18) | 0.061 (2) | 0.0439 (16) | 0.0034 (17) | 0.0202 (14) | 0.0044 (15) |
C12 | 0.082 (2) | 0.065 (2) | 0.0462 (17) | 0.0035 (19) | 0.0350 (17) | 0.0011 (16) |
C13 | 0.056 (2) | 0.081 (3) | 0.067 (2) | 0.004 (2) | 0.0321 (19) | 0.0281 (19) |
C14 | 0.057 (2) | 0.058 (2) | 0.0467 (18) | −0.0056 (16) | 0.0208 (16) | 0.0089 (15) |
C15 | 0.055 (2) | 0.066 (2) | 0.055 (2) | −0.0015 (18) | 0.0231 (16) | 0.0092 (17) |
C16 | 0.073 (3) | 0.055 (2) | 0.064 (2) | 0.0067 (19) | 0.0271 (18) | 0.0009 (17) |
C17 | 0.066 (3) | 0.075 (3) | 0.069 (2) | 0.017 (2) | 0.028 (2) | 0.019 (2) |
C18 | 0.075 (3) | 0.058 (2) | 0.0561 (19) | 0.001 (2) | 0.0228 (18) | −0.0050 (17) |
Geometric parameters (Å, º) top
N1—C12 | 1.345 (3) | C5—H5 | 0.99 (3) |
N1—C14 | 1.362 (3) | C6—C7 | 1.359 (3) |
N1—C11 | 1.457 (3) | C6—C10 | 1.431 (3) |
N2—C12 | 1.307 (4) | C6—C15 | 1.511 (4) |
N2—C13 | 1.365 (4) | C7—C8 | 1.403 (3) |
N3—C18 | 1.337 (3) | C7—H7 | 0.95 (2) |
N3—C16 | 1.366 (4) | C8—H8 | 0.95 (2) |
N3—C15 | 1.461 (3) | C9—C10 | 1.427 (3) |
N4—C18 | 1.312 (4) | C11—H111 | 1.03 (3) |
N4—C17 | 1.358 (4) | C11—H112 | 1.01 (2) |
C1—C8 | 1.363 (3) | C12—H12 | 1.01 (3) |
C1—C9 | 1.421 (3) | C13—C14 | 1.347 (4) |
C1—C11 | 1.507 (3) | C13—H13 | 0.88 (3) |
C2—C3 | 1.366 (4) | C14—H14 | 0.95 (3) |
C2—C9 | 1.414 (3) | C15—H151 | 0.96 (3) |
C2—H2 | 0.99 (2) | C15—H152 | 1.01 (2) |
C3—C4 | 1.390 (4) | C16—C17 | 1.348 (4) |
C3—H3 | 0.98 (3) | C16—H16 | 0.99 (3) |
C4—C5 | 1.357 (4) | C17—H17 | 0.92 (3) |
C4—H4 | 0.97 (2) | C18—H18 | 0.97 (3) |
C5—C10 | 1.420 (3) | | |
| | | |
C12—N1—C14 | 107.5 (3) | C1—C9—C10 | 120.3 (2) |
C12—N1—C11 | 125.9 (3) | C5—C10—C9 | 118.5 (2) |
C14—N1—C11 | 126.5 (2) | C5—C10—C6 | 122.6 (2) |
C12—N2—C13 | 104.0 (3) | C9—C10—C6 | 119.0 (2) |
C18—N3—C16 | 106.1 (3) | N1—C11—C1 | 113.8 (2) |
C18—N3—C15 | 125.5 (3) | N1—C11—H111 | 113.2 (13) |
C16—N3—C15 | 128.3 (3) | C1—C11—H111 | 108.3 (13) |
C18—N4—C17 | 104.0 (3) | N1—C11—H112 | 106.0 (13) |
C8—C1—C9 | 118.4 (2) | C1—C11—H112 | 110.6 (13) |
C8—C1—C11 | 122.0 (2) | H111—C11—H112 | 104.5 (18) |
C9—C1—C11 | 119.6 (2) | N2—C12—N1 | 112.0 (3) |
C3—C2—C9 | 121.5 (3) | N2—C12—H12 | 127.8 (17) |
C3—C2—H2 | 121.9 (12) | N1—C12—H12 | 120.2 (17) |
C9—C2—H2 | 116.6 (12) | C14—C13—N2 | 111.8 (3) |
C2—C3—C4 | 120.3 (3) | C14—C13—H13 | 123.2 (19) |
C2—C3—H3 | 118.9 (16) | N2—C13—H13 | 124.9 (19) |
C4—C3—H3 | 120.8 (16) | C13—C14—N1 | 104.6 (3) |
C5—C4—C3 | 120.5 (3) | C13—C14—H14 | 134.1 (18) |
C5—C4—H4 | 121.0 (15) | N1—C14—H14 | 121.1 (17) |
C3—C4—H4 | 118.5 (15) | N3—C15—C6 | 112.9 (2) |
C4—C5—C10 | 121.3 (3) | N3—C15—H151 | 106.4 (15) |
C4—C5—H5 | 122.4 (14) | C6—C15—H151 | 110.6 (16) |
C10—C5—H5 | 116.2 (15) | N3—C15—H152 | 105.1 (14) |
C7—C6—C10 | 118.6 (2) | C6—C15—H152 | 110.2 (14) |
C7—C6—C15 | 122.2 (3) | H151—C15—H152 | 111 (2) |
C10—C6—C15 | 119.2 (2) | C17—C16—N3 | 105.8 (3) |
C6—C7—C8 | 121.9 (3) | C17—C16—H16 | 134.0 (19) |
C6—C7—H7 | 122.1 (14) | N3—C16—H16 | 120.0 (18) |
C8—C7—H7 | 116.0 (14) | C16—C17—N4 | 111.1 (3) |
C1—C8—C7 | 121.6 (3) | C16—C17—H17 | 125 (2) |
C1—C8—H8 | 120.2 (12) | N4—C17—H17 | 124 (2) |
C7—C8—H8 | 118.1 (12) | N4—C18—N3 | 113.0 (3) |
C2—C9—C1 | 121.7 (2) | N4—C18—H18 | 126.8 (16) |
C2—C9—C10 | 118.0 (2) | N3—C18—H18 | 120.2 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···N1 | 0.95 (2) | 2.48 (2) | 2.828 (4) | 102 (2) |
C12—H12···N4i | 1.01 (3) | 2.55 (3) | 3.465 (5) | 152 (2) |
C14—H14···N2ii | 0.95 (3) | 2.53 (3) | 3.416 (4) | 155 (3) |
Symmetry codes: (i) x−1, y, z−1; (ii) x, −y+3/2, z+1/2. |
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