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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023009891/hb8081sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023009891/hb8081Isup2.hkl
Contains datablock I

cdx

Chemdraw file https://doi.org/10.1107/S2056989023009891/hb8081Isup3.cdx
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989023009891/hb8081Isup5.cml
Supplementary material

docx

Microsoft Word (DOCX) file https://doi.org/10.1107/S2056989023009891/hb8081sup4.docx
Supplementary figures: void volumes, energy frameworks and HOMO and LUMO

CCDC reference: 2307930

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](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

Computing details top

1,3-Bis[(1-octyl-1H-1,2,3-triazol-4-yl)methyl]-1H-benzo[d]imidazol-2(3H)-one top
Crystal data top
C29H44N8OF(000) = 564
Mr = 520.72Dx = 1.164 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 5.5229 (2) ÅCell parameters from 9942 reflections
b = 11.9579 (5) Åθ = 2.5–28.3°
c = 22.5767 (9) ŵ = 0.07 mm1
β = 94.962 (1)°T = 150 K
V = 1485.43 (10) Å3Plate, colourless
Z = 20.43 × 0.24 × 0.04 mm
Data collection top
Bruker D8 QUEST PHOTON 3
diffractometer
7403 independent reflections
Radiation source: fine-focus sealed tube6607 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 7.3910 pixels mm-1θmax = 28.3°, θmin = 1.8°
φ and ω scansh = 77
Absorption correction: numerical
(SADABS; Krause et al., 2015)
k = 1515
Tmin = 0.97, Tmax = 1.00l = 3030
44175 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-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 reflectionsΔρmax = 0.21 e Å3
346 parametersΔρmin = 0.15 e Å3
1 restraintAbsolute structure: Refined as an inversion twin
Primary atom site location: dualAbsolute 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
xyzUiso*/Ueq
O10.5165 (2)0.45034 (11)0.46448 (6)0.0329 (3)
N10.8422 (3)0.38162 (12)0.41592 (6)0.0266 (3)
N20.6546 (3)0.26610 (12)0.47315 (6)0.0256 (3)
N30.7105 (3)0.48912 (14)0.23204 (7)0.0308 (3)
N40.9528 (3)0.49012 (15)0.23032 (7)0.0357 (4)
N51.0483 (3)0.48764 (14)0.28579 (7)0.0343 (4)
N60.7789 (3)0.26119 (13)0.66306 (6)0.0276 (3)
N70.5441 (3)0.25415 (17)0.67279 (7)0.0402 (4)
N80.4205 (3)0.24210 (16)0.62051 (7)0.0377 (4)
C10.8325 (3)0.20418 (14)0.44791 (8)0.0261 (4)
C20.8978 (4)0.09248 (15)0.45373 (9)0.0316 (4)
H20.8167020.0428290.4782480.038*
C31.0882 (4)0.05678 (16)0.42184 (9)0.0358 (4)
H31.1380810.0192050.4246770.043*
C41.2070 (4)0.12896 (17)0.38608 (9)0.0363 (4)
H41.3370970.1014650.3652940.044*
C51.1398 (3)0.24138 (16)0.37988 (8)0.0308 (4)
H51.2195700.2908100.3549690.037*
C60.9523 (3)0.27692 (14)0.41167 (7)0.0256 (3)
C70.6557 (3)0.37503 (15)0.45279 (7)0.0255 (3)
C80.9182 (3)0.48505 (15)0.38886 (8)0.0286 (4)
H8A1.0947560.4956170.3989730.034*
H8B0.8327860.5486750.4058540.034*
C90.8673 (3)0.48614 (15)0.32269 (8)0.0269 (3)
C100.6497 (3)0.48710 (16)0.28838 (8)0.0304 (4)
H100.4909160.4864840.3015680.037*
C110.5501 (4)0.49558 (17)0.17728 (9)0.0363 (4)
H11A0.4241180.4367620.1778000.044*
H11B0.6455780.4810450.1429500.044*
C120.4278 (3)0.60839 (16)0.16948 (8)0.0316 (4)
H12A0.5538630.6668460.1675620.038*
H12B0.3375330.6240780.2045770.038*
C130.2529 (4)0.61468 (16)0.11355 (8)0.0325 (4)
H13A0.3471800.6129770.0782100.039*
H13B0.1457290.5481910.1118350.039*
C140.0970 (4)0.71974 (16)0.11140 (9)0.0325 (4)
H14A0.2053070.7858130.1146170.039*
H14B0.0004820.7200370.1463720.039*
C150.0758 (4)0.73133 (16)0.05545 (9)0.0340 (4)
H15A0.0207070.7369670.0205920.041*
H15B0.1768240.6630280.0505630.041*
C160.2417 (4)0.83263 (17)0.05645 (9)0.0346 (4)
H16A0.1400550.9007970.0609590.042*
H16B0.3358430.8273410.0917260.042*
C170.4187 (4)0.84527 (18)0.00121 (9)0.0418 (5)
H17A0.3251700.8553050.0338900.050*
H17B0.5147930.7756590.0046780.050*
C180.5909 (4)0.9431 (2)0.00497 (10)0.0454 (5)
H18A0.6972350.9482120.0319970.068*
H18B0.4971321.0123800.0108530.068*
H18C0.6898280.9319930.0384980.068*
C190.4857 (3)0.22611 (15)0.51395 (8)0.0288 (4)
H19A0.4533760.1457360.5062730.035*
H19B0.3298890.2667390.5063280.035*
C200.5775 (3)0.24109 (14)0.57782 (8)0.0257 (3)
C210.8082 (3)0.25252 (15)0.60465 (7)0.0259 (3)
H210.9561790.2540090.5861360.031*
C220.9617 (3)0.28057 (16)0.71286 (8)0.0312 (4)
H22A1.0961780.2264240.7106190.037*
H22B0.8876470.2672850.7506390.037*
C231.0639 (3)0.39888 (15)0.71301 (8)0.0298 (4)
H23A1.1467480.4111570.6763810.036*
H23B0.9293140.4534730.7133530.036*
C241.2429 (4)0.41756 (16)0.76706 (8)0.0312 (4)
H24A1.3563720.3533770.7710950.037*
H24B1.1523690.4195530.8030240.037*
C251.3899 (4)0.52512 (16)0.76421 (9)0.0335 (4)
H25A1.4782460.5241280.7278870.040*
H25B1.2773150.5896980.7613150.040*
C261.5718 (4)0.54024 (17)0.81829 (9)0.0356 (4)
H26A1.6778940.4734520.8221440.043*
H26B1.4815230.5441200.8542570.043*
C271.7314 (4)0.64393 (17)0.81632 (9)0.0374 (4)
H27A1.8199550.6412690.7800500.045*
H27B1.6266180.7112280.8137560.045*
C281.9139 (4)0.65407 (19)0.87038 (10)0.0439 (5)
H28A1.8248310.6570640.9065550.053*
H28B2.0172590.5862940.8730720.053*
C292.0762 (4)0.7564 (2)0.86910 (11)0.0512 (6)
H29A2.1921240.7567530.9045000.077*
H29B1.9761500.8241160.8686070.077*
H29C2.1649450.7542890.8333620.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0295 (7)0.0286 (6)0.0409 (8)0.0049 (5)0.0046 (6)0.0024 (6)
N10.0274 (7)0.0221 (7)0.0306 (8)0.0014 (6)0.0041 (6)0.0023 (6)
N20.0252 (7)0.0233 (7)0.0284 (7)0.0016 (6)0.0024 (6)0.0016 (6)
N30.0276 (7)0.0312 (8)0.0334 (8)0.0053 (7)0.0012 (6)0.0029 (7)
N40.0281 (8)0.0429 (9)0.0365 (9)0.0031 (7)0.0058 (7)0.0046 (8)
N50.0268 (7)0.0394 (9)0.0372 (9)0.0005 (7)0.0053 (7)0.0046 (7)
N60.0252 (7)0.0291 (7)0.0283 (7)0.0042 (6)0.0013 (6)0.0016 (6)
N70.0272 (8)0.0605 (11)0.0331 (8)0.0084 (8)0.0041 (7)0.0057 (8)
N80.0254 (8)0.0553 (11)0.0326 (8)0.0058 (7)0.0043 (6)0.0065 (8)
C10.0250 (8)0.0263 (8)0.0263 (9)0.0005 (7)0.0020 (7)0.0012 (7)
C20.0370 (10)0.0240 (8)0.0325 (10)0.0010 (8)0.0052 (8)0.0006 (7)
C30.0426 (11)0.0261 (9)0.0370 (11)0.0072 (8)0.0061 (9)0.0065 (8)
C40.0349 (10)0.0392 (11)0.0339 (10)0.0089 (8)0.0013 (8)0.0104 (8)
C50.0301 (9)0.0338 (10)0.0283 (9)0.0017 (7)0.0019 (7)0.0022 (7)
C60.0249 (8)0.0248 (8)0.0264 (8)0.0015 (7)0.0024 (7)0.0015 (7)
C70.0234 (8)0.0256 (8)0.0271 (8)0.0011 (7)0.0011 (7)0.0019 (7)
C80.0283 (8)0.0243 (8)0.0327 (9)0.0028 (7)0.0002 (7)0.0021 (7)
C90.0230 (8)0.0234 (7)0.0344 (9)0.0002 (7)0.0038 (7)0.0051 (7)
C100.0250 (8)0.0331 (9)0.0335 (9)0.0020 (8)0.0043 (7)0.0038 (8)
C110.0380 (10)0.0366 (10)0.0332 (10)0.0079 (9)0.0042 (8)0.0013 (8)
C120.0292 (9)0.0325 (9)0.0326 (9)0.0031 (7)0.0005 (8)0.0033 (7)
C130.0330 (10)0.0329 (10)0.0312 (9)0.0038 (7)0.0002 (8)0.0001 (7)
C140.0315 (9)0.0312 (9)0.0341 (10)0.0027 (8)0.0015 (8)0.0008 (7)
C150.0346 (10)0.0339 (10)0.0326 (10)0.0034 (8)0.0019 (8)0.0010 (7)
C160.0337 (10)0.0334 (9)0.0359 (10)0.0026 (8)0.0018 (8)0.0016 (8)
C170.0437 (12)0.0425 (12)0.0377 (11)0.0081 (9)0.0052 (9)0.0032 (9)
C180.0457 (12)0.0443 (12)0.0452 (13)0.0109 (10)0.0005 (10)0.0095 (10)
C190.0255 (8)0.0317 (9)0.0291 (9)0.0070 (7)0.0012 (7)0.0016 (7)
C200.0244 (8)0.0231 (8)0.0299 (9)0.0015 (6)0.0033 (7)0.0001 (6)
C210.0236 (8)0.0261 (8)0.0283 (8)0.0012 (7)0.0034 (7)0.0004 (7)
C220.0321 (9)0.0331 (9)0.0272 (9)0.0068 (8)0.0046 (7)0.0003 (7)
C230.0301 (9)0.0294 (9)0.0291 (9)0.0031 (7)0.0019 (7)0.0011 (7)
C240.0326 (10)0.0310 (9)0.0295 (9)0.0050 (7)0.0010 (8)0.0016 (7)
C250.0317 (10)0.0313 (9)0.0367 (11)0.0065 (8)0.0014 (8)0.0010 (8)
C260.0342 (10)0.0336 (10)0.0381 (11)0.0068 (8)0.0023 (9)0.0014 (8)
C270.0338 (10)0.0333 (10)0.0443 (11)0.0068 (8)0.0022 (9)0.0027 (9)
C280.0423 (12)0.0397 (11)0.0480 (12)0.0102 (10)0.0053 (10)0.0034 (9)
C290.0436 (12)0.0427 (12)0.0649 (15)0.0125 (10)0.0094 (11)0.0077 (11)
Geometric parameters (Å, º) top
O1—C71.227 (2)C14—H14B0.9900
N1—C71.382 (2)C15—C161.520 (3)
N1—C61.399 (2)C15—H15A0.9900
N1—C81.457 (2)C15—H15B0.9900
N2—C71.381 (2)C16—C171.524 (3)
N2—C11.391 (2)C16—H16A0.9900
N2—C191.448 (2)C16—H16B0.9900
N3—N41.342 (2)C17—C181.515 (3)
N3—C101.344 (2)C17—H17A0.9900
N3—C111.459 (2)C17—H17B0.9900
N4—N51.317 (2)C18—H18A0.9800
N5—C91.356 (2)C18—H18B0.9800
N6—N71.337 (2)C18—H18C0.9800
N6—C211.346 (2)C19—C201.498 (2)
N6—C221.463 (2)C19—H19A0.9900
N7—N81.319 (2)C19—H19B0.9900
N8—C201.351 (2)C20—C211.369 (2)
C1—C21.387 (2)C21—H210.9500
C1—C61.399 (2)C22—C231.523 (3)
C2—C31.392 (3)C22—H22A0.9900
C2—H20.9500C22—H22B0.9900
C3—C41.385 (3)C23—C241.519 (2)
C3—H30.9500C23—H23A0.9900
C4—C51.399 (3)C23—H23B0.9900
C4—H40.9500C24—C251.525 (3)
C5—C61.377 (3)C24—H24A0.9900
C5—H50.9500C24—H24B0.9900
C8—C91.496 (3)C25—C261.523 (3)
C8—H8A0.9900C25—H25A0.9900
C8—H8B0.9900C25—H25B0.9900
C9—C101.373 (2)C26—C271.524 (3)
C10—H100.9500C26—H26A0.9900
C11—C121.512 (3)C26—H26B0.9900
C11—H11A0.9900C27—C281.519 (3)
C11—H11B0.9900C27—H27A0.9900
C12—C131.524 (3)C27—H27B0.9900
C12—H12A0.9900C28—C291.518 (3)
C12—H12B0.9900C28—H28A0.9900
C13—C141.522 (3)C28—H28B0.9900
C13—H13A0.9900C29—H29A0.9800
C13—H13B0.9900C29—H29B0.9800
C14—C151.522 (2)C29—H29C0.9800
C14—H14A0.9900
C7—N1—C6109.97 (14)C15—C16—C17114.31 (17)
C7—N1—C8123.91 (14)C15—C16—H16A108.7
C6—N1—C8126.02 (14)C17—C16—H16A108.7
C7—N2—C1110.01 (14)C15—C16—H16B108.7
C7—N2—C19122.99 (15)C17—C16—H16B108.7
C1—N2—C19126.99 (15)H16A—C16—H16B107.6
N4—N3—C10111.05 (15)C18—C17—C16113.09 (17)
N4—N3—C11120.59 (15)C18—C17—H17A109.0
C10—N3—C11128.28 (15)C16—C17—H17A109.0
N5—N4—N3106.89 (14)C18—C17—H17B109.0
N4—N5—C9109.21 (15)C16—C17—H17B109.0
N7—N6—C21110.88 (14)H17A—C17—H17B107.8
N7—N6—C22119.89 (14)C17—C18—H18A109.5
C21—N6—C22129.19 (15)C17—C18—H18B109.5
N8—N7—N6107.11 (15)H18A—C18—H18B109.5
N7—N8—C20108.94 (15)C17—C18—H18C109.5
C2—C1—N2131.37 (18)H18A—C18—H18C109.5
C2—C1—C6121.48 (17)H18B—C18—H18C109.5
N2—C1—C6107.15 (15)N2—C19—C20112.93 (14)
C1—C2—C3116.63 (18)N2—C19—H19A109.0
C1—C2—H2121.7C20—C19—H19A109.0
C3—C2—H2121.7N2—C19—H19B109.0
C4—C3—C2121.84 (17)C20—C19—H19B109.0
C4—C3—H3119.1H19A—C19—H19B107.8
C2—C3—H3119.1N8—C20—C21108.28 (16)
C3—C4—C5121.48 (18)N8—C20—C19120.19 (15)
C3—C4—H4119.3C21—C20—C19131.51 (16)
C5—C4—H4119.3N6—C21—C20104.79 (15)
C6—C5—C4116.72 (18)N6—C21—H21127.6
C6—C5—H5121.6C20—C21—H21127.6
C4—C5—H5121.6N6—C22—C23112.32 (14)
C5—C6—N1131.52 (16)N6—C22—H22A109.1
C5—C6—C1121.85 (16)C23—C22—H22A109.1
N1—C6—C1106.63 (15)N6—C22—H22B109.1
O1—C7—N2126.84 (16)C23—C22—H22B109.1
O1—C7—N1126.95 (16)H22A—C22—H22B107.9
N2—C7—N1106.20 (14)C24—C23—C22110.72 (15)
N1—C8—C9112.95 (15)C24—C23—H23A109.5
N1—C8—H8A109.0C22—C23—H23A109.5
C9—C8—H8A109.0C24—C23—H23B109.5
N1—C8—H8B109.0C22—C23—H23B109.5
C9—C8—H8B109.0H23A—C23—H23B108.1
H8A—C8—H8B107.8C23—C24—C25113.69 (15)
N5—C9—C10108.03 (16)C23—C24—H24A108.8
N5—C9—C8121.92 (16)C25—C24—H24A108.8
C10—C9—C8130.05 (16)C23—C24—H24B108.8
N3—C10—C9104.82 (15)C25—C24—H24B108.8
N3—C10—H10127.6H24A—C24—H24B107.7
C9—C10—H10127.6C26—C25—C24112.51 (16)
N3—C11—C12112.22 (15)C26—C25—H25A109.1
N3—C11—H11A109.2C24—C25—H25A109.1
C12—C11—H11A109.2C26—C25—H25B109.1
N3—C11—H11B109.2C24—C25—H25B109.1
C12—C11—H11B109.2H25A—C25—H25B107.8
H11A—C11—H11B107.9C25—C26—C27114.60 (17)
C11—C12—C13112.66 (15)C25—C26—H26A108.6
C11—C12—H12A109.1C27—C26—H26A108.6
C13—C12—H12A109.1C25—C26—H26B108.6
C11—C12—H12B109.1C27—C26—H26B108.6
C13—C12—H12B109.1H26A—C26—H26B107.6
H12A—C12—H12B107.8C28—C27—C26112.76 (17)
C14—C13—C12112.57 (15)C28—C27—H27A109.0
C14—C13—H13A109.1C26—C27—H27A109.0
C12—C13—H13A109.1C28—C27—H27B109.0
C14—C13—H13B109.1C26—C27—H27B109.0
C12—C13—H13B109.1H27A—C27—H27B107.8
H13A—C13—H13B107.8C29—C28—C27113.62 (19)
C13—C14—C15114.46 (15)C29—C28—H28A108.8
C13—C14—H14A108.6C27—C28—H28A108.8
C15—C14—H14A108.6C29—C28—H28B108.8
C13—C14—H14B108.6C27—C28—H28B108.8
C15—C14—H14B108.6H28A—C28—H28B107.7
H14A—C14—H14B107.6C28—C29—H29A109.5
C16—C15—C14113.30 (16)C28—C29—H29B109.5
C16—C15—H15A108.9H29A—C29—H29B109.5
C14—C15—H15A108.9C28—C29—H29C109.5
C16—C15—H15B108.9H29A—C29—H29C109.5
C14—C15—H15B108.9H29B—C29—H29C109.5
H15A—C15—H15B107.7
C10—N3—N4—N50.6 (2)N4—N5—C9—C100.3 (2)
C11—N3—N4—N5177.67 (15)N4—N5—C9—C8179.02 (16)
N3—N4—N5—C90.6 (2)N1—C8—C9—N5113.96 (19)
C21—N6—N7—N80.7 (2)N1—C8—C9—C1066.8 (2)
C22—N6—N7—N8177.02 (16)N4—N3—C10—C90.4 (2)
N6—N7—N8—C200.2 (2)C11—N3—C10—C9177.17 (17)
C7—N2—C1—C2178.80 (18)N5—C9—C10—N30.0 (2)
C19—N2—C1—C20.0 (3)C8—C9—C10—N3179.31 (18)
C7—N2—C1—C61.31 (19)N4—N3—C11—C12107.0 (2)
C19—N2—C1—C6179.84 (15)C10—N3—C11—C1269.6 (2)
N2—C1—C2—C3179.77 (18)N3—C11—C12—C13177.95 (16)
C6—C1—C2—C30.1 (3)C11—C12—C13—C14169.67 (17)
C1—C2—C3—C40.0 (3)C12—C13—C14—C15178.35 (16)
C2—C3—C4—C50.5 (3)C13—C14—C15—C16175.90 (17)
C3—C4—C5—C60.9 (3)C14—C15—C16—C17179.27 (17)
C4—C5—C6—N1179.66 (17)C15—C16—C17—C18176.78 (18)
C4—C5—C6—C10.7 (3)C7—N2—C19—C2088.9 (2)
C7—N1—C6—C5178.61 (18)C1—N2—C19—C2092.4 (2)
C8—N1—C6—C54.8 (3)N7—N8—C20—C210.3 (2)
C7—N1—C6—C11.08 (18)N7—N8—C20—C19178.80 (16)
C8—N1—C6—C1175.52 (16)N2—C19—C20—N8159.08 (17)
C2—C1—C6—C50.2 (3)N2—C19—C20—C2122.8 (3)
N2—C1—C6—C5179.86 (15)N7—N6—C21—C200.8 (2)
C2—C1—C6—N1179.96 (16)C22—N6—C21—C20176.61 (16)
N2—C1—C6—N10.14 (18)N8—C20—C21—N60.6 (2)
C1—N2—C7—O1177.12 (17)C19—C20—C21—N6178.96 (17)
C19—N2—C7—O11.8 (3)N7—N6—C22—C23106.9 (2)
C1—N2—C7—N11.95 (18)C21—N6—C22—C2370.3 (2)
C19—N2—C7—N1179.15 (14)N6—C22—C23—C24177.04 (15)
C6—N1—C7—O1177.20 (17)C22—C23—C24—C25168.59 (16)
C8—N1—C7—O16.1 (3)C23—C24—C25—C26178.67 (17)
C6—N1—C7—N21.86 (18)C24—C25—C26—C27177.38 (17)
C8—N1—C7—N2174.83 (15)C25—C26—C27—C28178.60 (18)
C7—N1—C8—C9113.03 (18)C26—C27—C28—C29179.6 (2)
C6—N1—C8—C970.8 (2)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the N3–N5/C9/C10 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.952.593.502 (2)162
C10—H10···N5ii0.952.443.317 (2)153
C19—H19A···O1i0.992.433.334 (2)152
C21—H21···N8iii0.952.623.372 (2)137
C22—H22A···Cg2iv0.992.893.664 (2)135
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x1, y, z; (iii) x+1, y, z; (iv) x+2, y1/2, z+1.
Comparison of the selected (X-ray and DFT) geometric data (Å, °) top
Bonds/anglesX-rayB3LYP/6-311G(d,p)
O1—C71.227 (2)1.2256
N1—C71.382 (2)1.3862
N1—C61.399 (2)1.3954
N1—C81.457 (2)1.4529
N2—C71.381 (2)1.3838
N2—C11.391 (2)1.3957
N3—N41.342 (2)1.3447
N4—N51.317 (2)1.3118
N4—N3—C10111.05 (15)111.56
N4—N3—C11120.59 (15)120.32
C10—N3—C11128.28 (15)128.09
N5—N4—N3106.89 (14)106.96
N4—N5—C9109.21 (15)109.85
Calculated energies. top
Molecular 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 A0.68
Electronegativity χ3.202
Hardness η2.19
Softness σ0.19
Electrophilicity index ω2,03

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