The title molecule adopts a conformation resembling a two-bladed fan with the octyl chains in fully extended conformations. In the crystal, the molecules are linked by C—H
O and C—H
N hydrogen bonds and C—H
π interactions.
Supporting information
CCDC reference: 2307930
Key indicators
Structure: I
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.090
- Data-to-parameter ratio = 21.4
checkCIF/PLATON results
No syntax errors found
Alert level C
STRVA01_ALERT_4_C Flack test results are meaningless.
From the CIF: _refine_ls_abs_structure_Flack 0.200
From the CIF: _refine_ls_abs_structure_Flack_su 1.300
Alert level G
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High . 1.300 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 3 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter Values Differ by . 0.50 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 12 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by 2 Check
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
7 ALERT level G = General information/check it is not something unexpected
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
3 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
1,3-Bis[(1-octyl-1
H-1,2,3-triazol-4-yl)methyl]-1
H-benzo[
d]imidazol-2(3
H)-one
top
Crystal data top
C29H44N8O | F(000) = 564 |
Mr = 520.72 | Dx = 1.164 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.5229 (2) Å | Cell parameters from 9942 reflections |
b = 11.9579 (5) Å | θ = 2.5–28.3° |
c = 22.5767 (9) Å | µ = 0.07 mm−1 |
β = 94.962 (1)° | T = 150 K |
V = 1485.43 (10) Å3 | Plate, colourless |
Z = 2 | 0.43 × 0.24 × 0.04 mm |
Data collection top
Bruker D8 QUEST PHOTON 3 diffractometer | 7403 independent reflections |
Radiation source: fine-focus sealed tube | 6607 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Detector resolution: 7.3910 pixels mm-1 | θmax = 28.3°, θmin = 1.8° |
φ and ω scans | h = −7→7 |
Absorption correction: numerical (SADABS; Krause et al., 2015) | k = −15→15 |
Tmin = 0.97, Tmax = 1.00 | l = −30→30 |
44175 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0469P)2 + 0.1166P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
7403 reflections | Δρmax = 0.21 e Å−3 |
346 parameters | Δρmin = −0.15 e Å−3 |
1 restraint | Absolute structure: Refined as an inversion twin |
Primary atom site location: dual | Absolute structure parameter: 0.2 (13) |
Special details top
Experimental. The diffraction data were obtained from 7 sets of frames,
each of width 0.5° in ω or φ, collected with scan parameters
determined by the "strategy" routine in APEX3. The scan
time was 25 sec/frame. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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. H-atoms attached to carbon
were placed in calculated positions (C—H = 0.95 - 0.99 Å). All were
included as riding contributions with isotropic displacement parameters
1.2 - 1.5 times those of the attached atoms. Refined as a 2-component
inversion twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.5165 (2) | 0.45034 (11) | 0.46448 (6) | 0.0329 (3) | |
N1 | 0.8422 (3) | 0.38162 (12) | 0.41592 (6) | 0.0266 (3) | |
N2 | 0.6546 (3) | 0.26610 (12) | 0.47315 (6) | 0.0256 (3) | |
N3 | 0.7105 (3) | 0.48912 (14) | 0.23204 (7) | 0.0308 (3) | |
N4 | 0.9528 (3) | 0.49012 (15) | 0.23032 (7) | 0.0357 (4) | |
N5 | 1.0483 (3) | 0.48764 (14) | 0.28579 (7) | 0.0343 (4) | |
N6 | 0.7789 (3) | 0.26119 (13) | 0.66306 (6) | 0.0276 (3) | |
N7 | 0.5441 (3) | 0.25415 (17) | 0.67279 (7) | 0.0402 (4) | |
N8 | 0.4205 (3) | 0.24210 (16) | 0.62051 (7) | 0.0377 (4) | |
C1 | 0.8325 (3) | 0.20418 (14) | 0.44791 (8) | 0.0261 (4) | |
C2 | 0.8978 (4) | 0.09248 (15) | 0.45373 (9) | 0.0316 (4) | |
H2 | 0.816702 | 0.042829 | 0.478248 | 0.038* | |
C3 | 1.0882 (4) | 0.05678 (16) | 0.42184 (9) | 0.0358 (4) | |
H3 | 1.138081 | −0.019205 | 0.424677 | 0.043* | |
C4 | 1.2070 (4) | 0.12896 (17) | 0.38608 (9) | 0.0363 (4) | |
H4 | 1.337097 | 0.101465 | 0.365294 | 0.044* | |
C5 | 1.1398 (3) | 0.24138 (16) | 0.37988 (8) | 0.0308 (4) | |
H5 | 1.219570 | 0.290810 | 0.354969 | 0.037* | |
C6 | 0.9523 (3) | 0.27692 (14) | 0.41167 (7) | 0.0256 (3) | |
C7 | 0.6557 (3) | 0.37503 (15) | 0.45279 (7) | 0.0255 (3) | |
C8 | 0.9182 (3) | 0.48505 (15) | 0.38886 (8) | 0.0286 (4) | |
H8A | 1.094756 | 0.495617 | 0.398973 | 0.034* | |
H8B | 0.832786 | 0.548675 | 0.405854 | 0.034* | |
C9 | 0.8673 (3) | 0.48614 (15) | 0.32269 (8) | 0.0269 (3) | |
C10 | 0.6497 (3) | 0.48710 (16) | 0.28838 (8) | 0.0304 (4) | |
H10 | 0.490916 | 0.486484 | 0.301568 | 0.037* | |
C11 | 0.5501 (4) | 0.49558 (17) | 0.17728 (9) | 0.0363 (4) | |
H11A | 0.424118 | 0.436762 | 0.177800 | 0.044* | |
H11B | 0.645578 | 0.481045 | 0.142950 | 0.044* | |
C12 | 0.4278 (3) | 0.60839 (16) | 0.16948 (8) | 0.0316 (4) | |
H12A | 0.553863 | 0.666846 | 0.167562 | 0.038* | |
H12B | 0.337533 | 0.624078 | 0.204577 | 0.038* | |
C13 | 0.2529 (4) | 0.61468 (16) | 0.11355 (8) | 0.0325 (4) | |
H13A | 0.347180 | 0.612977 | 0.078210 | 0.039* | |
H13B | 0.145729 | 0.548191 | 0.111835 | 0.039* | |
C14 | 0.0970 (4) | 0.71974 (16) | 0.11140 (9) | 0.0325 (4) | |
H14A | 0.205307 | 0.785813 | 0.114617 | 0.039* | |
H14B | 0.000482 | 0.720037 | 0.146372 | 0.039* | |
C15 | −0.0758 (4) | 0.73133 (16) | 0.05545 (9) | 0.0340 (4) | |
H15A | 0.020707 | 0.736967 | 0.020592 | 0.041* | |
H15B | −0.176824 | 0.663028 | 0.050563 | 0.041* | |
C16 | −0.2417 (4) | 0.83263 (17) | 0.05645 (9) | 0.0346 (4) | |
H16A | −0.140055 | 0.900797 | 0.060959 | 0.042* | |
H16B | −0.335843 | 0.827341 | 0.091726 | 0.042* | |
C17 | −0.4187 (4) | 0.84527 (18) | 0.00121 (9) | 0.0418 (5) | |
H17A | −0.325170 | 0.855305 | −0.033890 | 0.050* | |
H17B | −0.514793 | 0.775659 | −0.004678 | 0.050* | |
C18 | −0.5909 (4) | 0.9431 (2) | 0.00497 (10) | 0.0454 (5) | |
H18A | −0.697235 | 0.948212 | −0.031997 | 0.068* | |
H18B | −0.497132 | 1.012380 | 0.010853 | 0.068* | |
H18C | −0.689828 | 0.931993 | 0.038498 | 0.068* | |
C19 | 0.4857 (3) | 0.22611 (15) | 0.51395 (8) | 0.0288 (4) | |
H19A | 0.453376 | 0.145736 | 0.506273 | 0.035* | |
H19B | 0.329889 | 0.266739 | 0.506328 | 0.035* | |
C20 | 0.5775 (3) | 0.24109 (14) | 0.57782 (8) | 0.0257 (3) | |
C21 | 0.8082 (3) | 0.25252 (15) | 0.60465 (7) | 0.0259 (3) | |
H21 | 0.956179 | 0.254009 | 0.586136 | 0.031* | |
C22 | 0.9617 (3) | 0.28057 (16) | 0.71286 (8) | 0.0312 (4) | |
H22A | 1.096178 | 0.226424 | 0.710619 | 0.037* | |
H22B | 0.887647 | 0.267285 | 0.750639 | 0.037* | |
C23 | 1.0639 (3) | 0.39888 (15) | 0.71301 (8) | 0.0298 (4) | |
H23A | 1.146748 | 0.411157 | 0.676381 | 0.036* | |
H23B | 0.929314 | 0.453473 | 0.713353 | 0.036* | |
C24 | 1.2429 (4) | 0.41756 (16) | 0.76706 (8) | 0.0312 (4) | |
H24A | 1.356372 | 0.353377 | 0.771095 | 0.037* | |
H24B | 1.152369 | 0.419553 | 0.803024 | 0.037* | |
C25 | 1.3899 (4) | 0.52512 (16) | 0.76421 (9) | 0.0335 (4) | |
H25A | 1.478246 | 0.524128 | 0.727887 | 0.040* | |
H25B | 1.277315 | 0.589698 | 0.761315 | 0.040* | |
C26 | 1.5718 (4) | 0.54024 (17) | 0.81829 (9) | 0.0356 (4) | |
H26A | 1.677894 | 0.473452 | 0.822144 | 0.043* | |
H26B | 1.481523 | 0.544120 | 0.854257 | 0.043* | |
C27 | 1.7314 (4) | 0.64393 (17) | 0.81632 (9) | 0.0374 (4) | |
H27A | 1.819955 | 0.641269 | 0.780050 | 0.045* | |
H27B | 1.626618 | 0.711228 | 0.813756 | 0.045* | |
C28 | 1.9139 (4) | 0.65407 (19) | 0.87038 (10) | 0.0439 (5) | |
H28A | 1.824831 | 0.657064 | 0.906555 | 0.053* | |
H28B | 2.017259 | 0.586294 | 0.873072 | 0.053* | |
C29 | 2.0762 (4) | 0.7564 (2) | 0.86910 (11) | 0.0512 (6) | |
H29A | 2.192124 | 0.756753 | 0.904500 | 0.077* | |
H29B | 1.976150 | 0.824116 | 0.868607 | 0.077* | |
H29C | 2.164945 | 0.754289 | 0.833362 | 0.077* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0295 (7) | 0.0286 (6) | 0.0409 (8) | 0.0049 (5) | 0.0046 (6) | −0.0024 (6) |
N1 | 0.0274 (7) | 0.0221 (7) | 0.0306 (8) | 0.0014 (6) | 0.0041 (6) | 0.0023 (6) |
N2 | 0.0252 (7) | 0.0233 (7) | 0.0284 (7) | −0.0016 (6) | 0.0024 (6) | 0.0016 (6) |
N3 | 0.0276 (7) | 0.0312 (8) | 0.0334 (8) | 0.0053 (7) | 0.0012 (6) | 0.0029 (7) |
N4 | 0.0281 (8) | 0.0429 (9) | 0.0365 (9) | 0.0031 (7) | 0.0058 (7) | 0.0046 (8) |
N5 | 0.0268 (7) | 0.0394 (9) | 0.0372 (9) | 0.0005 (7) | 0.0053 (7) | 0.0046 (7) |
N6 | 0.0252 (7) | 0.0291 (7) | 0.0283 (7) | −0.0042 (6) | 0.0013 (6) | −0.0016 (6) |
N7 | 0.0272 (8) | 0.0605 (11) | 0.0331 (8) | −0.0084 (8) | 0.0041 (7) | −0.0057 (8) |
N8 | 0.0254 (8) | 0.0553 (11) | 0.0326 (8) | −0.0058 (7) | 0.0043 (6) | −0.0065 (8) |
C1 | 0.0250 (8) | 0.0263 (8) | 0.0263 (9) | 0.0005 (7) | −0.0020 (7) | −0.0012 (7) |
C2 | 0.0370 (10) | 0.0240 (8) | 0.0325 (10) | −0.0010 (8) | −0.0052 (8) | −0.0006 (7) |
C3 | 0.0426 (11) | 0.0261 (9) | 0.0370 (11) | 0.0072 (8) | −0.0061 (9) | −0.0065 (8) |
C4 | 0.0349 (10) | 0.0392 (11) | 0.0339 (10) | 0.0089 (8) | −0.0013 (8) | −0.0104 (8) |
C5 | 0.0301 (9) | 0.0338 (10) | 0.0283 (9) | 0.0017 (7) | 0.0019 (7) | −0.0022 (7) |
C6 | 0.0249 (8) | 0.0248 (8) | 0.0264 (8) | 0.0015 (7) | −0.0024 (7) | −0.0015 (7) |
C7 | 0.0234 (8) | 0.0256 (8) | 0.0271 (8) | −0.0011 (7) | −0.0011 (7) | −0.0019 (7) |
C8 | 0.0283 (8) | 0.0243 (8) | 0.0327 (9) | −0.0028 (7) | −0.0002 (7) | 0.0021 (7) |
C9 | 0.0230 (8) | 0.0234 (7) | 0.0344 (9) | 0.0002 (7) | 0.0038 (7) | 0.0051 (7) |
C10 | 0.0250 (8) | 0.0331 (9) | 0.0335 (9) | 0.0020 (8) | 0.0043 (7) | 0.0038 (8) |
C11 | 0.0380 (10) | 0.0366 (10) | 0.0332 (10) | 0.0079 (9) | −0.0042 (8) | −0.0013 (8) |
C12 | 0.0292 (9) | 0.0325 (9) | 0.0326 (9) | 0.0031 (7) | 0.0005 (8) | 0.0033 (7) |
C13 | 0.0330 (10) | 0.0329 (10) | 0.0312 (9) | 0.0038 (7) | 0.0002 (8) | −0.0001 (7) |
C14 | 0.0315 (9) | 0.0312 (9) | 0.0341 (10) | 0.0027 (8) | −0.0015 (8) | −0.0008 (7) |
C15 | 0.0346 (10) | 0.0339 (10) | 0.0326 (10) | 0.0034 (8) | −0.0019 (8) | −0.0010 (7) |
C16 | 0.0337 (10) | 0.0334 (9) | 0.0359 (10) | 0.0026 (8) | −0.0018 (8) | 0.0016 (8) |
C17 | 0.0437 (12) | 0.0425 (12) | 0.0377 (11) | 0.0081 (9) | −0.0052 (9) | 0.0032 (9) |
C18 | 0.0457 (12) | 0.0443 (12) | 0.0452 (13) | 0.0109 (10) | −0.0005 (10) | 0.0095 (10) |
C19 | 0.0255 (8) | 0.0317 (9) | 0.0291 (9) | −0.0070 (7) | 0.0012 (7) | 0.0016 (7) |
C20 | 0.0244 (8) | 0.0231 (8) | 0.0299 (9) | −0.0015 (6) | 0.0033 (7) | −0.0001 (6) |
C21 | 0.0236 (8) | 0.0261 (8) | 0.0283 (8) | −0.0012 (7) | 0.0034 (7) | 0.0004 (7) |
C22 | 0.0321 (9) | 0.0331 (9) | 0.0272 (9) | −0.0068 (8) | −0.0046 (7) | 0.0003 (7) |
C23 | 0.0301 (9) | 0.0294 (9) | 0.0291 (9) | −0.0031 (7) | −0.0019 (7) | −0.0011 (7) |
C24 | 0.0326 (10) | 0.0310 (9) | 0.0295 (9) | −0.0050 (7) | −0.0010 (8) | −0.0016 (7) |
C25 | 0.0317 (10) | 0.0313 (9) | 0.0367 (11) | −0.0065 (8) | −0.0014 (8) | −0.0010 (8) |
C26 | 0.0342 (10) | 0.0336 (10) | 0.0381 (11) | −0.0068 (8) | −0.0023 (9) | −0.0014 (8) |
C27 | 0.0338 (10) | 0.0333 (10) | 0.0443 (11) | −0.0068 (8) | −0.0022 (9) | −0.0027 (9) |
C28 | 0.0423 (12) | 0.0397 (11) | 0.0480 (12) | −0.0102 (10) | −0.0053 (10) | −0.0034 (9) |
C29 | 0.0436 (12) | 0.0427 (12) | 0.0649 (15) | −0.0125 (10) | −0.0094 (11) | −0.0077 (11) |
Geometric parameters (Å, º) top
O1—C7 | 1.227 (2) | C14—H14B | 0.9900 |
N1—C7 | 1.382 (2) | C15—C16 | 1.520 (3) |
N1—C6 | 1.399 (2) | C15—H15A | 0.9900 |
N1—C8 | 1.457 (2) | C15—H15B | 0.9900 |
N2—C7 | 1.381 (2) | C16—C17 | 1.524 (3) |
N2—C1 | 1.391 (2) | C16—H16A | 0.9900 |
N2—C19 | 1.448 (2) | C16—H16B | 0.9900 |
N3—N4 | 1.342 (2) | C17—C18 | 1.515 (3) |
N3—C10 | 1.344 (2) | C17—H17A | 0.9900 |
N3—C11 | 1.459 (2) | C17—H17B | 0.9900 |
N4—N5 | 1.317 (2) | C18—H18A | 0.9800 |
N5—C9 | 1.356 (2) | C18—H18B | 0.9800 |
N6—N7 | 1.337 (2) | C18—H18C | 0.9800 |
N6—C21 | 1.346 (2) | C19—C20 | 1.498 (2) |
N6—C22 | 1.463 (2) | C19—H19A | 0.9900 |
N7—N8 | 1.319 (2) | C19—H19B | 0.9900 |
N8—C20 | 1.351 (2) | C20—C21 | 1.369 (2) |
C1—C2 | 1.387 (2) | C21—H21 | 0.9500 |
C1—C6 | 1.399 (2) | C22—C23 | 1.523 (3) |
C2—C3 | 1.392 (3) | C22—H22A | 0.9900 |
C2—H2 | 0.9500 | C22—H22B | 0.9900 |
C3—C4 | 1.385 (3) | C23—C24 | 1.519 (2) |
C3—H3 | 0.9500 | C23—H23A | 0.9900 |
C4—C5 | 1.399 (3) | C23—H23B | 0.9900 |
C4—H4 | 0.9500 | C24—C25 | 1.525 (3) |
C5—C6 | 1.377 (3) | C24—H24A | 0.9900 |
C5—H5 | 0.9500 | C24—H24B | 0.9900 |
C8—C9 | 1.496 (3) | C25—C26 | 1.523 (3) |
C8—H8A | 0.9900 | C25—H25A | 0.9900 |
C8—H8B | 0.9900 | C25—H25B | 0.9900 |
C9—C10 | 1.373 (2) | C26—C27 | 1.524 (3) |
C10—H10 | 0.9500 | C26—H26A | 0.9900 |
C11—C12 | 1.512 (3) | C26—H26B | 0.9900 |
C11—H11A | 0.9900 | C27—C28 | 1.519 (3) |
C11—H11B | 0.9900 | C27—H27A | 0.9900 |
C12—C13 | 1.524 (3) | C27—H27B | 0.9900 |
C12—H12A | 0.9900 | C28—C29 | 1.518 (3) |
C12—H12B | 0.9900 | C28—H28A | 0.9900 |
C13—C14 | 1.522 (3) | C28—H28B | 0.9900 |
C13—H13A | 0.9900 | C29—H29A | 0.9800 |
C13—H13B | 0.9900 | C29—H29B | 0.9800 |
C14—C15 | 1.522 (2) | C29—H29C | 0.9800 |
C14—H14A | 0.9900 | | |
| | | |
C7—N1—C6 | 109.97 (14) | C15—C16—C17 | 114.31 (17) |
C7—N1—C8 | 123.91 (14) | C15—C16—H16A | 108.7 |
C6—N1—C8 | 126.02 (14) | C17—C16—H16A | 108.7 |
C7—N2—C1 | 110.01 (14) | C15—C16—H16B | 108.7 |
C7—N2—C19 | 122.99 (15) | C17—C16—H16B | 108.7 |
C1—N2—C19 | 126.99 (15) | H16A—C16—H16B | 107.6 |
N4—N3—C10 | 111.05 (15) | C18—C17—C16 | 113.09 (17) |
N4—N3—C11 | 120.59 (15) | C18—C17—H17A | 109.0 |
C10—N3—C11 | 128.28 (15) | C16—C17—H17A | 109.0 |
N5—N4—N3 | 106.89 (14) | C18—C17—H17B | 109.0 |
N4—N5—C9 | 109.21 (15) | C16—C17—H17B | 109.0 |
N7—N6—C21 | 110.88 (14) | H17A—C17—H17B | 107.8 |
N7—N6—C22 | 119.89 (14) | C17—C18—H18A | 109.5 |
C21—N6—C22 | 129.19 (15) | C17—C18—H18B | 109.5 |
N8—N7—N6 | 107.11 (15) | H18A—C18—H18B | 109.5 |
N7—N8—C20 | 108.94 (15) | C17—C18—H18C | 109.5 |
C2—C1—N2 | 131.37 (18) | H18A—C18—H18C | 109.5 |
C2—C1—C6 | 121.48 (17) | H18B—C18—H18C | 109.5 |
N2—C1—C6 | 107.15 (15) | N2—C19—C20 | 112.93 (14) |
C1—C2—C3 | 116.63 (18) | N2—C19—H19A | 109.0 |
C1—C2—H2 | 121.7 | C20—C19—H19A | 109.0 |
C3—C2—H2 | 121.7 | N2—C19—H19B | 109.0 |
C4—C3—C2 | 121.84 (17) | C20—C19—H19B | 109.0 |
C4—C3—H3 | 119.1 | H19A—C19—H19B | 107.8 |
C2—C3—H3 | 119.1 | N8—C20—C21 | 108.28 (16) |
C3—C4—C5 | 121.48 (18) | N8—C20—C19 | 120.19 (15) |
C3—C4—H4 | 119.3 | C21—C20—C19 | 131.51 (16) |
C5—C4—H4 | 119.3 | N6—C21—C20 | 104.79 (15) |
C6—C5—C4 | 116.72 (18) | N6—C21—H21 | 127.6 |
C6—C5—H5 | 121.6 | C20—C21—H21 | 127.6 |
C4—C5—H5 | 121.6 | N6—C22—C23 | 112.32 (14) |
C5—C6—N1 | 131.52 (16) | N6—C22—H22A | 109.1 |
C5—C6—C1 | 121.85 (16) | C23—C22—H22A | 109.1 |
N1—C6—C1 | 106.63 (15) | N6—C22—H22B | 109.1 |
O1—C7—N2 | 126.84 (16) | C23—C22—H22B | 109.1 |
O1—C7—N1 | 126.95 (16) | H22A—C22—H22B | 107.9 |
N2—C7—N1 | 106.20 (14) | C24—C23—C22 | 110.72 (15) |
N1—C8—C9 | 112.95 (15) | C24—C23—H23A | 109.5 |
N1—C8—H8A | 109.0 | C22—C23—H23A | 109.5 |
C9—C8—H8A | 109.0 | C24—C23—H23B | 109.5 |
N1—C8—H8B | 109.0 | C22—C23—H23B | 109.5 |
C9—C8—H8B | 109.0 | H23A—C23—H23B | 108.1 |
H8A—C8—H8B | 107.8 | C23—C24—C25 | 113.69 (15) |
N5—C9—C10 | 108.03 (16) | C23—C24—H24A | 108.8 |
N5—C9—C8 | 121.92 (16) | C25—C24—H24A | 108.8 |
C10—C9—C8 | 130.05 (16) | C23—C24—H24B | 108.8 |
N3—C10—C9 | 104.82 (15) | C25—C24—H24B | 108.8 |
N3—C10—H10 | 127.6 | H24A—C24—H24B | 107.7 |
C9—C10—H10 | 127.6 | C26—C25—C24 | 112.51 (16) |
N3—C11—C12 | 112.22 (15) | C26—C25—H25A | 109.1 |
N3—C11—H11A | 109.2 | C24—C25—H25A | 109.1 |
C12—C11—H11A | 109.2 | C26—C25—H25B | 109.1 |
N3—C11—H11B | 109.2 | C24—C25—H25B | 109.1 |
C12—C11—H11B | 109.2 | H25A—C25—H25B | 107.8 |
H11A—C11—H11B | 107.9 | C25—C26—C27 | 114.60 (17) |
C11—C12—C13 | 112.66 (15) | C25—C26—H26A | 108.6 |
C11—C12—H12A | 109.1 | C27—C26—H26A | 108.6 |
C13—C12—H12A | 109.1 | C25—C26—H26B | 108.6 |
C11—C12—H12B | 109.1 | C27—C26—H26B | 108.6 |
C13—C12—H12B | 109.1 | H26A—C26—H26B | 107.6 |
H12A—C12—H12B | 107.8 | C28—C27—C26 | 112.76 (17) |
C14—C13—C12 | 112.57 (15) | C28—C27—H27A | 109.0 |
C14—C13—H13A | 109.1 | C26—C27—H27A | 109.0 |
C12—C13—H13A | 109.1 | C28—C27—H27B | 109.0 |
C14—C13—H13B | 109.1 | C26—C27—H27B | 109.0 |
C12—C13—H13B | 109.1 | H27A—C27—H27B | 107.8 |
H13A—C13—H13B | 107.8 | C29—C28—C27 | 113.62 (19) |
C13—C14—C15 | 114.46 (15) | C29—C28—H28A | 108.8 |
C13—C14—H14A | 108.6 | C27—C28—H28A | 108.8 |
C15—C14—H14A | 108.6 | C29—C28—H28B | 108.8 |
C13—C14—H14B | 108.6 | C27—C28—H28B | 108.8 |
C15—C14—H14B | 108.6 | H28A—C28—H28B | 107.7 |
H14A—C14—H14B | 107.6 | C28—C29—H29A | 109.5 |
C16—C15—C14 | 113.30 (16) | C28—C29—H29B | 109.5 |
C16—C15—H15A | 108.9 | H29A—C29—H29B | 109.5 |
C14—C15—H15A | 108.9 | C28—C29—H29C | 109.5 |
C16—C15—H15B | 108.9 | H29A—C29—H29C | 109.5 |
C14—C15—H15B | 108.9 | H29B—C29—H29C | 109.5 |
H15A—C15—H15B | 107.7 | | |
| | | |
C10—N3—N4—N5 | 0.6 (2) | N4—N5—C9—C10 | 0.3 (2) |
C11—N3—N4—N5 | 177.67 (15) | N4—N5—C9—C8 | −179.02 (16) |
N3—N4—N5—C9 | −0.6 (2) | N1—C8—C9—N5 | −113.96 (19) |
C21—N6—N7—N8 | −0.7 (2) | N1—C8—C9—C10 | 66.8 (2) |
C22—N6—N7—N8 | 177.02 (16) | N4—N3—C10—C9 | −0.4 (2) |
N6—N7—N8—C20 | 0.2 (2) | C11—N3—C10—C9 | −177.17 (17) |
C7—N2—C1—C2 | −178.80 (18) | N5—C9—C10—N3 | 0.0 (2) |
C19—N2—C1—C2 | 0.0 (3) | C8—C9—C10—N3 | 179.31 (18) |
C7—N2—C1—C6 | 1.31 (19) | N4—N3—C11—C12 | −107.0 (2) |
C19—N2—C1—C6 | −179.84 (15) | C10—N3—C11—C12 | 69.6 (2) |
N2—C1—C2—C3 | −179.77 (18) | N3—C11—C12—C13 | −177.95 (16) |
C6—C1—C2—C3 | 0.1 (3) | C11—C12—C13—C14 | 169.67 (17) |
C1—C2—C3—C4 | 0.0 (3) | C12—C13—C14—C15 | 178.35 (16) |
C2—C3—C4—C5 | −0.5 (3) | C13—C14—C15—C16 | 175.90 (17) |
C3—C4—C5—C6 | 0.9 (3) | C14—C15—C16—C17 | −179.27 (17) |
C4—C5—C6—N1 | 179.66 (17) | C15—C16—C17—C18 | 176.78 (18) |
C4—C5—C6—C1 | −0.7 (3) | C7—N2—C19—C20 | −88.9 (2) |
C7—N1—C6—C5 | 178.61 (18) | C1—N2—C19—C20 | 92.4 (2) |
C8—N1—C6—C5 | −4.8 (3) | N7—N8—C20—C21 | 0.3 (2) |
C7—N1—C6—C1 | −1.08 (18) | N7—N8—C20—C19 | 178.80 (16) |
C8—N1—C6—C1 | 175.52 (16) | N2—C19—C20—N8 | 159.08 (17) |
C2—C1—C6—C5 | 0.2 (3) | N2—C19—C20—C21 | −22.8 (3) |
N2—C1—C6—C5 | −179.86 (15) | N7—N6—C21—C20 | 0.8 (2) |
C2—C1—C6—N1 | 179.96 (16) | C22—N6—C21—C20 | −176.61 (16) |
N2—C1—C6—N1 | −0.14 (18) | N8—C20—C21—N6 | −0.6 (2) |
C1—N2—C7—O1 | 177.12 (17) | C19—C20—C21—N6 | −178.96 (17) |
C19—N2—C7—O1 | −1.8 (3) | N7—N6—C22—C23 | −106.9 (2) |
C1—N2—C7—N1 | −1.95 (18) | C21—N6—C22—C23 | 70.3 (2) |
C19—N2—C7—N1 | 179.15 (14) | N6—C22—C23—C24 | 177.04 (15) |
C6—N1—C7—O1 | −177.20 (17) | C22—C23—C24—C25 | 168.59 (16) |
C8—N1—C7—O1 | 6.1 (3) | C23—C24—C25—C26 | −178.67 (17) |
C6—N1—C7—N2 | 1.86 (18) | C24—C25—C26—C27 | 177.38 (17) |
C8—N1—C7—N2 | −174.83 (15) | C25—C26—C27—C28 | −178.60 (18) |
C7—N1—C8—C9 | −113.03 (18) | C26—C27—C28—C29 | 179.6 (2) |
C6—N1—C8—C9 | 70.8 (2) | | |
Hydrogen-bond geometry (Å, º) topCg2 is the centroid of the N3–N5/C9/C10 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.95 | 2.59 | 3.502 (2) | 162 |
C10—H10···N5ii | 0.95 | 2.44 | 3.317 (2) | 153 |
C19—H19A···O1i | 0.99 | 2.43 | 3.334 (2) | 152 |
C21—H21···N8iii | 0.95 | 2.62 | 3.372 (2) | 137 |
C22—H22A···Cg2iv | 0.99 | 2.89 | 3.664 (2) | 135 |
Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x−1, y, z; (iii) x+1, y, z; (iv) −x+2, y−1/2, −z+1. |
Comparison of the selected (X-ray and DFT) geometric data
(Å, °) topBonds/angles | X-ray | B3LYP/6-311G(d,p) |
O1—C7 | 1.227 (2) | 1.2256 |
N1—C7 | 1.382 (2) | 1.3862 |
N1—C6 | 1.399 (2) | 1.3954 |
N1—C8 | 1.457 (2) | 1.4529 |
N2—C7 | 1.381 (2) | 1.3838 |
N2—C1 | 1.391 (2) | 1.3957 |
N3—N4 | 1.342 (2) | 1.3447 |
N4—N5 | 1.317 (2) | 1.3118 |
N4—N3—C10 | 111.05 (15) | 111.56 |
N4—N3—C11 | 120.59 (15) | 120.32 |
C10—N3—C11 | 128.28 (15) | 128.09 |
N5—N4—N3 | 106.89 (14) | 106.96 |
N4—N5—C9 | 109.21 (15) | 109.85 |
Calculated energies. topMolecular Energy (a.u.) (eV) | Compound (I) |
Total Energy TE (eV) | –44752.35 |
EHOMO (eV) | –5.72 |
ELUMO (eV) | –0.68 |
Gap ΔE (eV) | 5.04 |
Dipole moment µ (Debye) | 3.96 |
Ionisation potential I (eV) | 5.72 |
Electron affinity A | 0.68 |
Electronegativity χ | 3.202 |
Hardness η | 2.19 |
Softness σ | 0.19 |
Electrophilicity index ω | 2,03 |