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The title compound, C
11H
8N
2, contains two essentially planar molecules (
A and
B) in the asymmetric unit. Molecules of type
B exhibit π–π stacking and form infinite zigzag chains along the
a axis.
A and
B molecules are linked by N
amine—H
N
imine hydrogen bonds and form polymeric –
A–
B–
A–
B– criss-crossed chains approximately along the [110] and [
10] directions. The
A molecules show little evidence of π stacking and, in addition to the hydrogen bonds, appear to be held in the crystal structure primarily by C—H
π interactions. The geometric parameters of molecules
A and
B agree well with each other and, where comparisons are appropriate, with those of a naphthimidazolium cation.
Supporting information
CCDC reference: 251760
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.007 Å
- R factor = 0.046
- wR factor = 0.110
- Data-to-parameter ratio = 6.1
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.778 1.000
Tmin' and Tmax expected: 0.962 0.998
RR' = 0.808
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.81
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.09
PLAT128_ALERT_4_C Non-standard setting of Space group Cc .... Ia
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
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 25.09
From the CIF: _reflns_number_total 1480
Count of symmetry unique reflns 1489
Completeness (_total/calc) 99.40%
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
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).
1H–napth[2,3-
d]imidazole
top
Crystal data top
C11H8N2 | F(000) = 704 |
Mr = 168.19 | Dx = 1.342 Mg m−3 |
Monoclinic, Ia | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: I -2ya | Cell parameters from 730 reflections |
a = 9.4503 (6) Å | θ = 2.3–20.8° |
b = 16.3882 (8) Å | µ = 0.08 mm−1 |
c = 11.4770 (9) Å | T = 295 K |
β = 110.502 (4)° | Plate, pale yellow |
V = 1664.90 (19) Å3 | 0.47 × 0.22 × 0.02 mm |
Z = 8 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 1480 independent reflections |
Radiation source: fine-focus sealed tube | 1145 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
φ and ω scans | θmax = 25.1°, θmin = 3.8° |
Absorption correction: multi-scan (SADABS; Blessing 1995) | h = −11→10 |
Tmin = 0.778, Tmax = 1.00 | k = −19→19 |
5846 measured reflections | l = −13→13 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0653P)2] where P = (Fo2 + 2Fc2)/3 |
1480 reflections | (Δ/σ)max < 0.001 |
243 parameters | Δρmax = 0.14 e Å−3 |
2 restraints | Δρmin = −0.13 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 | |
N11 | 0.7357 (4) | 0.2087 (2) | 0.8088 (3) | 0.0461 (9) | |
N13 | 0.6300 (4) | 0.1046 (2) | 0.6851 (3) | 0.0482 (9) | |
C11 | 0.6057 (4) | 0.1915 (2) | 0.8331 (3) | 0.0387 (10) | |
C12 | 0.7428 (5) | 0.1565 (3) | 0.7215 (4) | 0.0480 (10) | |
H12 | 0.8205 | 0.1569 | 0.6894 | 0.058* | |
C13 | 0.5392 (4) | 0.1247 (2) | 0.7551 (3) | 0.0395 (10) | |
C14 | 0.4075 (5) | 0.0916 (2) | 0.7566 (3) | 0.0453 (10) | |
H14 | 0.3631 | 0.0480 | 0.7049 | 0.054* | |
C15 | 0.3398 (5) | 0.1246 (3) | 0.8379 (3) | 0.0444 (10) | |
C15A | 0.2020 (5) | 0.0934 (3) | 0.8434 (4) | 0.0539 (12) | |
H15A | 0.1551 | 0.0501 | 0.7920 | 0.065* | |
C15B | 0.1376 (6) | 0.1247 (3) | 0.9207 (4) | 0.0606 (13) | |
H15B | 0.0474 | 0.1030 | 0.9222 | 0.073* | |
C16 | 0.4103 (5) | 0.1912 (2) | 0.9175 (3) | 0.0435 (10) | |
C16A | 0.3385 (6) | 0.2219 (3) | 0.9996 (4) | 0.0532 (12) | |
H16A | 0.3837 | 0.2641 | 1.0540 | 0.064* | |
C16B | 0.2058 (6) | 0.1904 (3) | 0.9995 (4) | 0.0634 (14) | |
H16B | 0.1595 | 0.2123 | 1.0519 | 0.076* | |
C17 | 0.5450 (5) | 0.2252 (2) | 0.9143 (3) | 0.0456 (11) | |
H17 | 0.5913 | 0.2688 | 0.9652 | 0.055* | |
H11 | 0.797 (6) | 0.245 (3) | 0.844 (4) | 0.056 (14)* | |
N21 | 0.4759 (4) | −0.0239 (2) | 0.5107 (3) | 0.0481 (9) | |
N23 | 0.3630 (4) | −0.1421 (2) | 0.4366 (3) | 0.0496 (9) | |
C21 | 0.3392 (4) | −0.0028 (3) | 0.4217 (3) | 0.0431 (10) | |
C22 | 0.4817 (5) | −0.1065 (3) | 0.5137 (4) | 0.0471 (11) | |
H22 | 0.5639 | −0.1354 | 0.5665 | 0.057* | |
C23 | 0.2681 (4) | −0.0775 (2) | 0.3758 (3) | 0.0409 (10) | |
C24 | 0.1293 (5) | −0.0783 (3) | 0.2820 (4) | 0.0462 (11) | |
H24 | 0.0820 | −0.1275 | 0.2509 | 0.055* | |
C25 | 0.0602 (4) | −0.0038 (3) | 0.2341 (3) | 0.0443 (11) | |
C25A | −0.0828 (5) | −0.0003 (3) | 0.1375 (4) | 0.0543 (12) | |
H25A | −0.1321 | −0.0488 | 0.1051 | 0.065* | |
C25B | −0.1492 (5) | 0.0711 (3) | 0.0911 (4) | 0.0604 (13) | |
H25B | −0.2420 | 0.0712 | 0.0264 | 0.072* | |
C26 | 0.1329 (5) | 0.0719 (3) | 0.2832 (3) | 0.0446 (10) | |
C26A | 0.0573 (5) | 0.1453 (3) | 0.2326 (4) | 0.0548 (12) | |
H26A | 0.1024 | 0.1950 | 0.2638 | 0.066* | |
C26B | −0.0798 (5) | 0.1449 (3) | 0.1393 (4) | 0.0598 (12) | |
H26B | −0.1274 | 0.1940 | 0.1077 | 0.072* | |
C27 | 0.2754 (5) | 0.0711 (3) | 0.3780 (4) | 0.0477 (11) | |
H27 | 0.3250 | 0.1195 | 0.4103 | 0.057* | |
H21 | 0.543 (6) | 0.010 (3) | 0.552 (4) | 0.071 (16)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.044 (2) | 0.039 (2) | 0.0478 (19) | −0.0121 (17) | 0.0060 (16) | −0.0105 (17) |
N13 | 0.053 (2) | 0.041 (2) | 0.0464 (17) | −0.0035 (18) | 0.0119 (16) | −0.0088 (16) |
C11 | 0.043 (2) | 0.027 (2) | 0.038 (2) | 0.0010 (18) | 0.0050 (18) | 0.0029 (16) |
C12 | 0.048 (2) | 0.050 (3) | 0.046 (2) | −0.005 (2) | 0.0170 (18) | −0.003 (2) |
C13 | 0.043 (2) | 0.033 (2) | 0.0338 (18) | 0.0022 (18) | 0.0022 (17) | 0.0014 (15) |
C14 | 0.048 (3) | 0.038 (2) | 0.039 (2) | −0.009 (2) | 0.0030 (17) | −0.0051 (18) |
C15 | 0.043 (2) | 0.045 (2) | 0.0372 (18) | 0.006 (2) | 0.0042 (16) | 0.0081 (18) |
C15A | 0.045 (3) | 0.059 (3) | 0.051 (2) | −0.002 (2) | 0.009 (2) | 0.006 (2) |
C15B | 0.050 (3) | 0.063 (3) | 0.067 (3) | 0.005 (3) | 0.018 (2) | 0.016 (3) |
C16 | 0.052 (2) | 0.037 (2) | 0.0363 (18) | 0.004 (2) | 0.0087 (17) | 0.0019 (17) |
C16A | 0.073 (3) | 0.037 (2) | 0.050 (2) | 0.011 (2) | 0.022 (2) | 0.0023 (19) |
C16B | 0.075 (4) | 0.057 (3) | 0.069 (3) | 0.020 (3) | 0.040 (3) | 0.019 (2) |
C17 | 0.053 (3) | 0.032 (2) | 0.042 (2) | −0.001 (2) | 0.0042 (18) | −0.0027 (18) |
N21 | 0.045 (2) | 0.045 (2) | 0.0471 (19) | −0.0099 (18) | 0.0080 (16) | −0.0148 (17) |
N23 | 0.054 (2) | 0.042 (2) | 0.0468 (18) | −0.0066 (17) | 0.0103 (16) | −0.0059 (16) |
C21 | 0.044 (3) | 0.043 (2) | 0.040 (2) | −0.007 (2) | 0.011 (2) | −0.0076 (19) |
C22 | 0.049 (2) | 0.047 (3) | 0.041 (2) | 0.004 (2) | 0.0107 (18) | −0.0022 (19) |
C23 | 0.045 (2) | 0.037 (2) | 0.0387 (19) | −0.0041 (19) | 0.0132 (17) | −0.0057 (18) |
C24 | 0.051 (3) | 0.036 (2) | 0.050 (2) | −0.0134 (19) | 0.015 (2) | −0.0082 (18) |
C25 | 0.047 (2) | 0.047 (3) | 0.042 (2) | −0.009 (2) | 0.0190 (19) | −0.0058 (19) |
C25A | 0.053 (3) | 0.054 (3) | 0.050 (2) | −0.008 (2) | 0.013 (2) | −0.004 (2) |
C25B | 0.057 (3) | 0.067 (3) | 0.049 (2) | 0.011 (3) | 0.008 (2) | 0.004 (2) |
C26 | 0.052 (3) | 0.047 (3) | 0.041 (2) | −0.001 (2) | 0.022 (2) | −0.0044 (19) |
C26A | 0.070 (3) | 0.042 (3) | 0.060 (2) | 0.000 (2) | 0.032 (2) | −0.005 (2) |
C26B | 0.071 (3) | 0.049 (3) | 0.055 (2) | 0.010 (3) | 0.017 (2) | 0.004 (2) |
C27 | 0.053 (3) | 0.040 (3) | 0.048 (2) | −0.010 (2) | 0.017 (2) | −0.009 (2) |
Geometric parameters (Å, º) top
N11—C12 | 1.337 (5) | N21—C22 | 1.355 (5) |
N11—C11 | 1.381 (5) | N21—C21 | 1.381 (5) |
N11—H11 | 0.83 (5) | N21—H21 | 0.85 (5) |
N13—C12 | 1.313 (5) | N23—C22 | 1.299 (5) |
N13—C13 | 1.404 (5) | N23—C23 | 1.405 (5) |
C11—C17 | 1.369 (6) | C21—C27 | 1.368 (6) |
C11—C13 | 1.415 (5) | C21—C23 | 1.406 (5) |
C12—H12 | 0.9300 | C22—H22 | 0.9300 |
C13—C14 | 1.363 (6) | C23—C24 | 1.375 (5) |
C14—C15 | 1.412 (6) | C24—C25 | 1.403 (6) |
C14—H14 | 0.9300 | C24—H24 | 0.9300 |
C15—C15A | 1.421 (6) | C25—C25A | 1.417 (6) |
C15—C16 | 1.430 (6) | C25—C26 | 1.434 (6) |
C15A—C15B | 1.341 (7) | C25A—C25B | 1.346 (6) |
C15A—H15A | 0.9300 | C25A—H25A | 0.9300 |
C15B—C16B | 1.409 (7) | C25B—C26B | 1.395 (7) |
C15B—H15B | 0.9300 | C25B—H25B | 0.9300 |
C16—C17 | 1.402 (6) | C26—C27 | 1.404 (6) |
C16—C16A | 1.431 (6) | C26—C26A | 1.416 (7) |
C16A—C16B | 1.356 (7) | C26A—C26B | 1.362 (6) |
C16A—H16A | 0.9300 | C26A—H26A | 0.9300 |
C16B—H16B | 0.9300 | C26B—H26B | 0.9300 |
C17—H17 | 0.9300 | C27—H27 | 0.9300 |
| | | |
C12—N11—C11 | 107.6 (3) | C22—N21—C21 | 106.7 (3) |
C12—N11—H11 | 128 (3) | C22—N21—H21 | 128 (3) |
C11—N11—H11 | 124 (3) | C21—N21—H21 | 125 (3) |
C12—N13—C13 | 104.8 (3) | C22—N23—C23 | 104.4 (3) |
C17—C11—N11 | 132.0 (4) | C27—C21—N21 | 132.1 (4) |
C17—C11—C13 | 122.9 (4) | C27—C21—C23 | 122.8 (3) |
N11—C11—C13 | 105.0 (3) | N21—C21—C23 | 105.1 (3) |
N13—C12—N11 | 113.9 (4) | N23—C22—N21 | 114.5 (4) |
N13—C12—H12 | 123.0 | N23—C22—H22 | 122.8 |
N11—C12—H12 | 123.0 | N21—C22—H22 | 122.8 |
C14—C13—N13 | 131.1 (3) | C24—C23—N23 | 130.5 (4) |
C14—C13—C11 | 120.3 (4) | C24—C23—C21 | 120.1 (4) |
N13—C13—C11 | 108.6 (3) | N23—C23—C21 | 109.4 (3) |
C13—C14—C15 | 118.9 (4) | C23—C24—C25 | 118.9 (4) |
C13—C14—H14 | 120.6 | C23—C24—H24 | 120.6 |
C15—C14—H14 | 120.6 | C25—C24—H24 | 120.6 |
C14—C15—C15A | 121.8 (4) | C24—C25—C25A | 121.8 (4) |
C14—C15—C16 | 119.8 (4) | C24—C25—C26 | 120.4 (3) |
C15A—C15—C16 | 118.4 (4) | C25A—C25—C26 | 117.8 (4) |
C15B—C15A—C15 | 121.8 (5) | C25B—C25A—C25 | 122.0 (4) |
C15B—C15A—H15A | 119.1 | C25B—C25A—H25A | 119.0 |
C15—C15A—H15A | 119.1 | C25—C25A—H25A | 119.0 |
C15A—C15B—C16B | 120.4 (5) | C25A—C25B—C26B | 120.5 (4) |
C15A—C15B—H15B | 119.8 | C25A—C25B—H25B | 119.7 |
C16B—C15B—H15B | 119.8 | C26B—C25B—H25B | 119.7 |
C17—C16—C15 | 120.7 (4) | C27—C26—C26A | 122.3 (4) |
C17—C16—C16A | 121.5 (4) | C27—C26—C25 | 119.6 (4) |
C15—C16—C16A | 117.8 (4) | C26A—C26—C25 | 118.1 (4) |
C16B—C16A—C16 | 121.2 (4) | C26B—C26A—C26 | 121.5 (5) |
C16B—C16A—H16A | 119.4 | C26B—C26A—H26A | 119.2 |
C16—C16A—H16A | 119.4 | C26—C26A—H26A | 119.2 |
C16A—C16B—C15B | 120.4 (5) | C26A—C26B—C25B | 120.1 (5) |
C16A—C16B—H16B | 119.8 | C26A—C26B—H26B | 119.9 |
C15B—C16B—H16B | 119.8 | C25B—C26B—H26B | 119.9 |
C11—C17—C16 | 117.3 (4) | C21—C27—C26 | 118.2 (4) |
C11—C17—H17 | 121.3 | C21—C27—H27 | 120.9 |
C16—C17—H17 | 121.4 | C26—C27—H27 | 120.9 |
| | | |
C12—N11—C11—C17 | 179.1 (4) | C22—N21—C21—C27 | −178.4 (4) |
C12—N11—C11—C13 | 0.9 (4) | C22—N21—C21—C23 | 0.6 (4) |
C13—N13—C12—N11 | 0.2 (4) | C23—N23—C22—N21 | 0.1 (5) |
C11—N11—C12—N13 | −0.7 (5) | C21—N21—C22—N23 | −0.4 (5) |
C12—N13—C13—C14 | 179.9 (4) | C22—N23—C23—C24 | 177.7 (4) |
C12—N13—C13—C11 | 0.4 (4) | C22—N23—C23—C21 | 0.3 (4) |
C17—C11—C13—C14 | 1.2 (5) | C27—C21—C23—C24 | 0.8 (6) |
N11—C11—C13—C14 | 179.6 (3) | N21—C21—C23—C24 | −178.3 (4) |
C17—C11—C13—N13 | −179.2 (3) | C27—C21—C23—N23 | 178.5 (4) |
N11—C11—C13—N13 | −0.8 (4) | N21—C21—C23—N23 | −0.6 (4) |
N13—C13—C14—C15 | 179.9 (4) | N23—C23—C24—C25 | −177.6 (4) |
C11—C13—C14—C15 | −0.6 (5) | C21—C23—C24—C25 | −0.5 (6) |
C13—C14—C15—C15A | 179.5 (4) | C23—C24—C25—C25A | 180.0 (4) |
C13—C14—C15—C16 | −0.5 (5) | C23—C24—C25—C26 | −0.6 (5) |
C14—C15—C15A—C15B | 180.0 (4) | C24—C25—C25A—C25B | −179.8 (4) |
C16—C15—C15A—C15B | 0.0 (6) | C26—C25—C25A—C25B | 0.7 (6) |
C15—C15A—C15B—C16B | 0.1 (7) | C25—C25A—C25B—C26B | −1.4 (7) |
C14—C15—C16—C17 | 1.1 (5) | C24—C25—C26—C27 | 1.3 (5) |
C15A—C15—C16—C17 | −178.9 (4) | C25A—C25—C26—C27 | −179.3 (4) |
C14—C15—C16—C16A | −179.1 (3) | C24—C25—C26—C26A | −179.2 (4) |
C15A—C15—C16—C16A | 0.9 (5) | C25A—C25—C26—C26A | 0.3 (5) |
C17—C16—C16A—C16B | 177.9 (4) | C27—C26—C26A—C26B | 179.0 (4) |
C15—C16—C16A—C16B | −1.8 (5) | C25—C26—C26A—C26B | −0.6 (6) |
C16—C16A—C16B—C15B | 1.9 (6) | C26—C26A—C26B—C25B | −0.1 (7) |
C15A—C15B—C16B—C16A | −1.0 (7) | C25A—C25B—C26B—C26A | 1.1 (7) |
N11—C11—C17—C16 | −178.5 (4) | N21—C21—C27—C26 | 178.7 (4) |
C13—C11—C17—C16 | −0.6 (5) | C23—C21—C27—C26 | −0.1 (6) |
C15—C16—C17—C11 | −0.5 (5) | C26A—C26—C27—C21 | 179.6 (4) |
C16A—C16—C17—C11 | 179.7 (4) | C25—C26—C27—C21 | −0.9 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···N23i | 0.83 (5) | 2.12 (5) | 2.888 (5) | 155 (5) |
N21—H21···N13 | 0.85 (5) | 2.13 (5) | 2.919 (5) | 154 (5) |
Symmetry code: (i) x+1/2, y+1/2, z+1/2. |
Interatomic N···C and C···C distances (Å), for molecules
of type B, which lie within the range generally accepted for
π–π interactions. Symmetry code: (i) x+1/2, -y, z. topN21···C25i | 3.562 (6) | C22···C26ai | 3.596 (7) |
N21···C26i | 3.515 (6) | C22···C27i | 3.673 (7) |
N21···C27i | 3.734 (7) | C23···C25ai | 3.714 (7) |
N23···C26i | 3.752 (6) | C23···C25bi | 3.618 (7) |
N23···C26ai | 3.445 (7) | C23···C26bi | 3.659 (7) |
N23···C26bi | 3.637 (6) | C24···C25bi | 3.523 (8) |
C21···C25i | 3.486 (6) | C27···C25i | 3.782 (7) |
C21···C25ai | 3.588 (6) | C27···C25ai | 3.655 (7) |
C22···C26i | 3.465 (7) | | |
Interatomic C···H distances less than 3.25 Å between
an A molecule and its nearest neighbors. Symmetry codes:
(i) x+1/2, y+1/2, x+1/2; (ii) x+1, y, z+1; (iii) x, -y+1/2, -1/2+z;
(iv) x+1, y, z; (v) x+1, -y+1/2, z+1/2; (vi) x+1/2, -y, z; (vii)
x+1/2, -y, z+1; (viii) x-1/2, -y, z; (ix) x, -y+1/2, z+1/2. topC11···H24 | 3.10i | C15a···H25a | 2.95vii |
C11···H25b | 2.94ii | C15b···H25a | 2.75vii |
C11···H16a | 3.24iii | C16···H27 | 3.20ix |
C12···H15b | 3.12iv | C16a···H25a | 3.06vii |
C12···H17 | 3.04iii | C16a···H26a | 3.15ix |
C12···H26b | 3.22v | C16a···H27 | 2.95ix |
C13···H15a | 3.04vi | C16b···H25a | 2.81vii |
C13···H16a | 2.90iii | C16b···H26a | 3.15ix |
C13···H25b | 3.20ii | C17···H24 | 3.15i |
C14···H15a | 3.22vi | C17···H25b | 3.20ii |
C15···H25a | 3.23vii | C17···H26b | 3.16ii |
C15a···H22 | 3.10viii | | |
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