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The asymmetric unit of the title compound consists of two mol­ecules differing to a small degree in their conformations. In the crystal, layers of mol­ecules are connected by weak C—H...O hydrogen bonds and slipped π-stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023007624/hb8072sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023007624/hb8072Isup2.hkl
Contains datablock I

cdx

Chemdraw file https://doi.org/10.1107/S2056989023007624/hb8072Isup3.cdx
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989023007624/hb8072Isup4.cml
Supplementary material

CCDC reference: 2292321

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 240 K
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in main residue
  • R factor = 0.047
  • wR factor = 0.137
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -0.023 Report PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 6 Report
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 5 Note PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 2 Report PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records 1 Report PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records 1 Report PLAT189_ALERT_3_G A Non-default SAME Restraint Value for First Par 0.0030 Report PLAT191_ALERT_3_G A Non-default SADI Restraint Value has been used 0.0030 Report PLAT230_ALERT_2_G Hirshfeld Test Diff for C21 --C22 . 7.7 s.u. PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 11% Note PLAT410_ALERT_2_G Short Intra H...H Contact H17 ..H21A . 2.07 Ang. x,y,z = 1_555 Check PLAT412_ALERT_2_G Short Intra XH3 .. XHn H17 ..H22C . 2.11 Ang. x,y,z = 1_555 Check PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 2 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 6 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 3 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 9 Info PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by 5 Check
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 15 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 7 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

3-Ethoxy-1-ethyl-6-nitroquinoxalin-2(1H)-one top
Crystal data top
C12H13N3O4F(000) = 1104
Mr = 263.25Dx = 1.405 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 14.4848 (3) ÅCell parameters from 9131 reflections
b = 12.5663 (2) Åθ = 3.6–74.5°
c = 15.2708 (3) ŵ = 0.91 mm1
β = 116.424 (1)°T = 240 K
V = 2489.20 (8) Å3Plate, colourless
Z = 80.25 × 0.16 × 0.09 mm
Data collection top
Bruker D8 VENTURE PHOTON 3 CPAD
diffractometer
5082 independent reflections
Radiation source: INCOATEC IµS micro–focus source4257 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.031
Detector resolution: 7.3910 pixels mm-1θmax = 74.6°, θmin = 3.5°
φ and ω scansh = 1818
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
k = 1515
Tmin = 0.81, Tmax = 0.93l = 1919
66682 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0675P)2 + 0.623P]
where P = (Fo2 + 2Fc2)/3
5082 reflections(Δ/σ)max < 0.001
355 parametersΔρmax = 0.31 e Å3
2 restraintsΔρmin = 0.24 e Å3
Special details top

Experimental. The diffraction data were obtained from 18 sets of frames, each of width 0.5° in ω or φ, collected with scan parameters determined by the "strategy" routine in APEX4. The scan time was θ-dependent and ranged from 5 to 15 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. The C21-C22 ethyl group is disordered over two resolved sites in a 0.584 (3)/0.416 (3) ratio and the two components were refined with restraints that their geometries be comparable

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.58896 (9)0.18517 (10)0.72886 (8)0.0684 (3)
O20.56752 (8)0.02104 (9)0.75322 (7)0.0577 (3)
O30.19338 (10)0.15645 (11)0.26502 (10)0.0782 (4)
O40.14323 (14)0.01613 (14)0.17867 (10)0.1109 (6)
N10.44938 (10)0.18526 (10)0.57903 (9)0.0511 (3)
N20.44267 (8)0.03747 (10)0.59520 (8)0.0467 (3)
N30.19358 (11)0.06088 (12)0.25626 (10)0.0642 (4)
C10.38082 (10)0.01493 (11)0.50836 (9)0.0426 (3)
C20.31774 (10)0.04604 (11)0.42806 (10)0.0464 (3)
H20.3172390.1205870.4328850.056*
C30.25591 (10)0.00398 (12)0.34124 (10)0.0492 (3)
C40.25135 (11)0.11315 (13)0.33181 (11)0.0541 (3)
H40.2064290.1452740.2724250.065*
C50.31383 (12)0.17440 (12)0.41099 (11)0.0539 (3)
H50.3115840.2489700.4055760.065*
C60.38049 (10)0.12651 (11)0.49926 (10)0.0450 (3)
C70.52019 (11)0.13682 (13)0.66320 (10)0.0517 (3)
C80.50543 (10)0.02007 (12)0.66644 (10)0.0473 (3)
C90.45860 (15)0.30158 (13)0.57188 (13)0.0666 (4)
H9A0.4881410.3326440.6375980.080*
H9B0.3898830.3322890.5343640.080*
C100.52561 (17)0.32914 (14)0.52314 (14)0.0766 (5)
H10A0.4971120.2974610.4584850.115*
H10B0.5946510.3019140.5619570.115*
H10C0.5283190.4058430.5175080.115*
C110.56054 (13)0.13524 (13)0.76522 (11)0.0605 (4)
H11A0.5793460.1743110.7199640.073*
H11B0.4901080.1550180.7520610.073*
C120.63413 (19)0.16070 (19)0.86897 (13)0.0921 (7)
H12A0.6326030.2365540.8800350.138*
H12B0.6141220.1221580.9128690.138*
H12C0.7032980.1398770.8811650.138*
O50.41594 (10)0.27601 (10)0.77918 (9)0.0750 (4)
O60.41831 (8)0.47798 (9)0.73392 (7)0.0588 (3)
O70.78801 (11)0.68361 (11)1.19824 (10)0.0799 (4)
O80.85032 (11)0.55613 (13)1.30161 (9)0.0905 (5)
N40.54742 (11)0.29975 (11)0.93216 (11)0.0677 (4)
N50.54324 (8)0.51731 (9)0.88781 (8)0.0468 (3)
N60.79426 (10)0.58951 (13)1.21966 (10)0.0627 (4)
C130.60770 (10)0.47806 (11)0.98025 (9)0.0438 (3)
C140.66831 (10)0.54983 (11)1.05191 (10)0.0461 (3)
H140.6651030.6229191.0377180.055*
C150.73319 (10)0.51310 (12)1.14396 (10)0.0498 (3)
C160.74255 (12)0.40606 (14)1.16725 (11)0.0578 (4)
H160.7895130.3826911.2298240.069*
C170.68202 (12)0.33456 (13)1.09731 (12)0.0621 (4)
H170.6868870.2616281.1123910.075*
C180.61299 (11)0.36931 (12)1.00359 (11)0.0518 (3)
C190.47782 (11)0.33450 (13)0.84112 (11)0.0564 (4)
C200.48407 (10)0.45019 (12)0.82464 (10)0.0483 (3)
C210.5397 (4)0.1885 (2)0.9655 (3)0.0725 (10)0.584 (3)
H21A0.5451040.1906281.0317820.087*0.584 (3)
H21B0.4728380.1573860.9218770.087*0.584 (3)
C220.6251 (3)0.1219 (3)0.9644 (3)0.0948 (10)0.584 (3)
H22A0.6215540.1233230.8994170.142*0.584 (3)
H22B0.6179650.0492160.9817550.142*0.584 (3)
H22C0.6909940.1502271.0111300.142*0.584 (3)
C21A0.5585 (6)0.1809 (2)0.9319 (4)0.0725 (10)0.416 (3)
H21C0.5345300.1525730.8656010.087*0.416 (3)
H21D0.6296010.1579390.9725570.087*0.416 (3)
C22A0.4881 (5)0.1506 (4)0.9761 (4)0.0948 (10)0.416 (3)
H22D0.4183250.1728930.9330200.142*0.416 (3)
H22E0.5107620.1854041.0390320.142*0.416 (3)
H22F0.4897360.0741010.9848640.142*0.416 (3)
C230.41646 (13)0.58928 (14)0.70810 (11)0.0630 (4)
H23A0.4816970.6095610.7078990.076*
H23B0.4055510.6345210.7549410.076*
C240.32870 (16)0.60100 (19)0.60766 (13)0.0839 (6)
H24A0.3244610.6743670.5864530.126*
H24B0.2647400.5811560.6092300.126*
H24C0.3402190.5550570.5624290.126*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0666 (7)0.0702 (7)0.0516 (6)0.0133 (6)0.0110 (5)0.0110 (5)
O20.0527 (6)0.0681 (7)0.0402 (5)0.0037 (5)0.0097 (4)0.0060 (5)
O30.0808 (8)0.0657 (8)0.0680 (8)0.0162 (6)0.0149 (6)0.0151 (6)
O40.1185 (12)0.0978 (11)0.0523 (7)0.0217 (9)0.0196 (7)0.0053 (7)
N10.0575 (7)0.0460 (6)0.0439 (6)0.0005 (5)0.0173 (5)0.0048 (5)
N20.0428 (6)0.0522 (6)0.0410 (6)0.0024 (5)0.0151 (5)0.0053 (5)
N30.0571 (7)0.0682 (9)0.0499 (7)0.0110 (6)0.0081 (6)0.0044 (6)
C10.0391 (6)0.0471 (7)0.0400 (6)0.0016 (5)0.0162 (5)0.0023 (5)
C20.0431 (7)0.0463 (7)0.0456 (7)0.0025 (5)0.0159 (6)0.0014 (5)
C30.0422 (7)0.0564 (8)0.0417 (7)0.0047 (6)0.0120 (6)0.0020 (6)
C40.0495 (7)0.0581 (8)0.0430 (7)0.0032 (6)0.0100 (6)0.0086 (6)
C50.0583 (8)0.0459 (7)0.0497 (8)0.0044 (6)0.0170 (7)0.0054 (6)
C60.0448 (7)0.0469 (7)0.0407 (7)0.0022 (5)0.0167 (5)0.0017 (5)
C70.0499 (7)0.0587 (8)0.0431 (7)0.0020 (6)0.0177 (6)0.0057 (6)
C80.0420 (6)0.0581 (8)0.0389 (6)0.0022 (6)0.0154 (5)0.0031 (6)
C90.0817 (11)0.0442 (8)0.0587 (9)0.0015 (7)0.0177 (8)0.0096 (7)
C100.0962 (14)0.0537 (9)0.0664 (11)0.0152 (9)0.0242 (10)0.0010 (8)
C110.0582 (9)0.0647 (10)0.0496 (8)0.0100 (7)0.0160 (7)0.0133 (7)
C120.1129 (17)0.0938 (15)0.0472 (9)0.0270 (13)0.0154 (10)0.0162 (9)
O50.0672 (7)0.0703 (8)0.0665 (7)0.0164 (6)0.0108 (6)0.0165 (6)
O60.0545 (6)0.0687 (7)0.0395 (5)0.0039 (5)0.0084 (4)0.0010 (5)
O70.0814 (8)0.0699 (8)0.0713 (8)0.0128 (7)0.0185 (7)0.0192 (6)
O80.0821 (9)0.1119 (12)0.0456 (6)0.0207 (8)0.0003 (6)0.0032 (7)
N40.0618 (8)0.0444 (7)0.0686 (9)0.0033 (6)0.0035 (7)0.0003 (6)
N50.0449 (6)0.0510 (6)0.0392 (6)0.0030 (5)0.0142 (5)0.0021 (5)
N60.0524 (7)0.0794 (10)0.0474 (7)0.0110 (6)0.0144 (6)0.0106 (6)
C130.0399 (6)0.0477 (7)0.0403 (7)0.0019 (5)0.0149 (5)0.0016 (5)
C140.0445 (7)0.0477 (7)0.0438 (7)0.0011 (5)0.0175 (6)0.0002 (5)
C150.0420 (7)0.0613 (9)0.0408 (7)0.0039 (6)0.0138 (6)0.0030 (6)
C160.0495 (8)0.0668 (9)0.0446 (7)0.0032 (7)0.0097 (6)0.0087 (7)
C170.0602 (9)0.0518 (8)0.0576 (9)0.0039 (7)0.0111 (7)0.0118 (7)
C180.0463 (7)0.0472 (7)0.0500 (8)0.0001 (6)0.0107 (6)0.0014 (6)
C190.0471 (7)0.0573 (9)0.0537 (8)0.0030 (6)0.0125 (6)0.0081 (7)
C200.0422 (7)0.0564 (8)0.0413 (7)0.0035 (6)0.0139 (5)0.0013 (6)
C210.094 (2)0.0477 (12)0.063 (3)0.0111 (13)0.0230 (18)0.0014 (13)
C220.147 (3)0.0596 (16)0.0650 (16)0.0060 (19)0.0352 (18)0.0036 (13)
C21A0.094 (2)0.0477 (12)0.063 (3)0.0111 (13)0.0230 (18)0.0014 (13)
C22A0.147 (3)0.0596 (16)0.0650 (16)0.0060 (19)0.0352 (18)0.0036 (13)
C230.0613 (9)0.0723 (10)0.0449 (8)0.0092 (8)0.0142 (7)0.0088 (7)
C240.0837 (13)0.1014 (15)0.0454 (9)0.0179 (11)0.0098 (9)0.0116 (9)
Geometric parameters (Å, º) top
O1—C71.2156 (18)O8—N61.2234 (19)
O2—C81.3308 (16)N4—C191.376 (2)
O2—C111.456 (2)N4—C181.3906 (19)
O3—N31.2084 (19)N4—C21A1.503 (3)
O4—N31.2178 (19)N4—C211.509 (3)
N1—C71.3789 (18)N5—C201.2809 (18)
N1—C61.3938 (17)N5—C131.3909 (16)
N1—C91.4762 (19)N6—C151.4597 (19)
N2—C81.2856 (18)C13—C141.3880 (19)
N2—C11.3920 (16)C13—C181.406 (2)
N3—C31.4563 (18)C14—C151.3771 (19)
C1—C21.3886 (18)C14—H140.9400
C1—C61.4088 (19)C15—C161.382 (2)
C2—C31.3777 (19)C16—C171.372 (2)
C2—H20.9400C16—H160.9400
C3—C41.378 (2)C17—C181.402 (2)
C4—C51.378 (2)C17—H170.9400
C4—H40.9400C19—C201.485 (2)
C5—C61.3975 (19)C21—C221.500 (5)
C5—H50.9400C21—H21A0.9800
C7—C81.487 (2)C21—H21B0.9800
C9—C101.503 (3)C22—H22A0.9700
C9—H9A0.9800C22—H22B0.9700
C9—H9B0.9800C22—H22C0.9700
C10—H10A0.9700C21A—C22A1.500 (5)
C10—H10B0.9700C21A—H21C0.9800
C10—H10C0.9700C21A—H21D0.9800
C11—C121.499 (2)C22A—H22D0.9700
C11—H11A0.9800C22A—H22E0.9700
C11—H11B0.9800C22A—H22F0.9700
C12—H12A0.9700C23—C241.502 (2)
C12—H12B0.9700C23—H23A0.9800
C12—H12C0.9700C23—H23B0.9800
O5—C191.2181 (18)C24—H24A0.9700
O6—C201.3320 (16)C24—H24B0.9700
O6—C231.450 (2)C24—H24C0.9700
O7—N61.219 (2)
C8—O2—C11117.00 (12)O7—N6—O8122.89 (15)
C7—N1—C6121.81 (12)O7—N6—C15118.61 (13)
C7—N1—C9116.86 (12)O8—N6—C15118.49 (15)
C6—N1—C9120.86 (12)C14—C13—N5118.24 (12)
C8—N2—C1116.94 (12)C14—C13—C18119.19 (12)
O3—N3—O4122.46 (15)N5—C13—C18122.57 (12)
O3—N3—C3119.25 (13)C15—C14—C13119.46 (13)
O4—N3—C3118.29 (15)C15—C14—H14120.3
C2—C1—N2118.15 (12)C13—C14—H14120.3
C2—C1—C6119.35 (12)C14—C15—C16122.21 (14)
N2—C1—C6122.50 (12)C14—C15—N6119.06 (14)
C3—C2—C1119.25 (13)C16—C15—N6118.73 (13)
C3—C2—H2120.4C17—C16—C15118.77 (14)
C1—C2—H2120.4C17—C16—H16120.6
C2—C3—C4122.36 (13)C15—C16—H16120.6
C2—C3—N3118.81 (13)C16—C17—C18120.60 (15)
C4—C3—N3118.83 (13)C16—C17—H17119.7
C3—C4—C5118.82 (13)C18—C17—H17119.7
C3—C4—H4120.6N4—C18—C17122.21 (14)
C5—C4—H4120.6N4—C18—C13118.09 (13)
C4—C5—C6120.52 (14)C17—C18—C13119.69 (13)
C4—C5—H5119.7O5—C19—N4123.26 (15)
C6—C5—H5119.7O5—C19—C20122.57 (15)
N1—C6—C5122.24 (13)N4—C19—C20114.17 (13)
N1—C6—C1118.12 (12)N5—C20—O6122.66 (14)
C5—C6—C1119.62 (12)N5—C20—C19126.01 (13)
O1—C7—N1123.01 (15)O6—C20—C19111.33 (12)
O1—C7—C8122.88 (14)C22—C21—N4109.1 (3)
N1—C7—C8114.10 (12)C22—C21—H21A109.9
N2—C8—O2122.29 (13)N4—C21—H21A109.9
N2—C8—C7125.80 (12)C22—C21—H21B109.9
O2—C8—C7111.89 (12)N4—C21—H21B109.9
N1—C9—C10111.37 (14)H21A—C21—H21B108.3
N1—C9—H9A109.4C21—C22—H22A109.5
C10—C9—H9A109.4C21—C22—H22B109.5
N1—C9—H9B109.4H22A—C22—H22B109.5
C10—C9—H9B109.4C21—C22—H22C109.5
H9A—C9—H9B108.0H22A—C22—H22C109.5
C9—C10—H10A109.5H22B—C22—H22C109.5
C9—C10—H10B109.5C22A—C21A—N499.0 (4)
H10A—C10—H10B109.5C22A—C21A—H21C112.0
C9—C10—H10C109.5N4—C21A—H21C112.0
H10A—C10—H10C109.5C22A—C21A—H21D112.0
H10B—C10—H10C109.5N4—C21A—H21D112.0
O2—C11—C12106.68 (15)H21C—C21A—H21D109.7
O2—C11—H11A110.4C21A—C22A—H22D109.5
C12—C11—H11A110.4C21A—C22A—H22E109.5
O2—C11—H11B110.4H22D—C22A—H22E109.5
C12—C11—H11B110.4C21A—C22A—H22F109.5
H11A—C11—H11B108.6H22D—C22A—H22F109.5
C11—C12—H12A109.5H22E—C22A—H22F109.5
C11—C12—H12B109.5O6—C23—C24106.09 (15)
H12A—C12—H12B109.5O6—C23—H23A110.5
C11—C12—H12C109.5C24—C23—H23A110.5
H12A—C12—H12C109.5O6—C23—H23B110.5
H12B—C12—H12C109.5C24—C23—H23B110.5
C20—O6—C23116.99 (12)H23A—C23—H23B108.7
C19—N4—C18122.06 (13)C23—C24—H24A109.5
C19—N4—C21A110.1 (3)C23—C24—H24B109.5
C18—N4—C21A126.2 (3)H24A—C24—H24B109.5
C19—N4—C21120.3 (2)C23—C24—H24C109.5
C18—N4—C21116.4 (2)H24A—C24—H24C109.5
C20—N5—C13116.92 (12)H24B—C24—H24C109.5
C8—N2—C1—C2175.40 (12)C18—C13—C14—C150.7 (2)
C8—N2—C1—C64.29 (19)C13—C14—C15—C161.9 (2)
N2—C1—C2—C3179.92 (12)C13—C14—C15—N6178.12 (12)
C6—C1—C2—C30.21 (19)O7—N6—C15—C142.0 (2)
C1—C2—C3—C42.4 (2)O8—N6—C15—C14178.77 (14)
C1—C2—C3—N3177.23 (12)O7—N6—C15—C16178.01 (15)
O3—N3—C3—C23.8 (2)O8—N6—C15—C161.2 (2)
O4—N3—C3—C2176.32 (17)C14—C15—C16—C172.7 (2)
O3—N3—C3—C4176.54 (15)N6—C15—C16—C17177.32 (14)
O4—N3—C3—C43.3 (2)C15—C16—C17—C180.9 (3)
C2—C3—C4—C52.6 (2)C19—N4—C18—C17178.21 (16)
N3—C3—C4—C5177.08 (14)C21A—N4—C18—C1717.8 (4)
C3—C4—C5—C60.1 (2)C21—N4—C18—C1711.0 (3)
C7—N1—C6—C5175.02 (13)C19—N4—C18—C130.8 (2)
C9—N1—C6—C53.1 (2)C21A—N4—C18—C13163.2 (3)
C7—N1—C6—C13.41 (19)C21—N4—C18—C13168.0 (2)
C9—N1—C6—C1175.31 (13)C16—C17—C18—N4177.29 (16)
C4—C5—C6—N1175.95 (13)C16—C17—C18—C131.7 (2)
C4—C5—C6—C12.5 (2)C14—C13—C18—N4176.54 (13)
C2—C1—C6—N1175.89 (12)N5—C13—C18—N43.0 (2)
N2—C1—C6—N13.80 (19)C14—C13—C18—C172.5 (2)
C2—C1—C6—C52.6 (2)N5—C13—C18—C17177.98 (13)
N2—C1—C6—C5177.72 (12)C18—N4—C19—O5176.01 (16)
C6—N1—C7—O1170.86 (14)C21A—N4—C19—O517.7 (3)
C9—N1—C7—O11.3 (2)C21—N4—C19—O59.3 (3)
C6—N1—C7—C88.83 (19)C18—N4—C19—C203.7 (2)
C9—N1—C7—C8178.96 (13)C21A—N4—C19—C20162.6 (3)
C1—N2—C8—O2179.26 (11)C21—N4—C19—C20170.4 (2)
C1—N2—C8—C72.2 (2)C13—N5—C20—O6179.47 (12)
C11—O2—C8—N20.9 (2)C13—N5—C20—C190.2 (2)
C11—O2—C8—C7179.69 (12)C23—O6—C20—N50.5 (2)
O1—C7—C8—N2171.07 (14)C23—O6—C20—C19179.92 (13)
N1—C7—C8—N28.6 (2)O5—C19—C20—N5176.16 (15)
O1—C7—C8—O27.6 (2)N4—C19—C20—N53.6 (2)
N1—C7—C8—O2172.67 (12)O5—C19—C20—O63.2 (2)
C7—N1—C9—C1091.55 (17)N4—C19—C20—O6177.06 (13)
C6—N1—C9—C1080.74 (18)C19—N4—C21—C22106.9 (3)
C8—O2—C11—C12177.81 (14)C18—N4—C21—C2285.6 (3)
C20—N5—C13—C14176.30 (12)C19—N4—C21A—C22A98.8 (4)
C20—N5—C13—C183.2 (2)C18—N4—C21A—C22A95.6 (5)
N5—C13—C14—C15179.71 (12)C20—O6—C23—C24173.60 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11A···O3i0.982.593.250 (2)125
C16—H16···O5ii0.942.583.2624 (19)130
C22—H22A···O10.972.553.487 (4)162
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x+1/2, y+1/2, z+1/2.
Comparison of the selected (X-ray and DFT) geometric data (Å, °) top
Bonds/anglesX-rayB3LYP/6-311G(d,p)
O1—C71.2156 (18)1.2145
O2—C81.3308 (16)1.3257
O2—C111.456 (2)1.4490
O3—N31.2084 (19)1.2236
O4—N31.2178 (19)1.2254
C8—O2—C11117.00 (12)117.61
C7—N1—C6121.81 (12)122.08
C6—N1—C9120.86 (12)121.09
O3—N3—O4122.46 (15)123.09
O1—C7—N1123.01 (15)123.12
Calculated energies. top
Molecular Energy (a.u.) (eV)Compound (I)
Total Energy TE (eV)-25316,62
EHOMO (eV)-6.56
ELUMO (eV)-2.16
Gap ΔE (eV)4.39
Dipole moment µ (Debye)2.93
Ionisation potential I (eV)6.56
Electron affinity A2.16
Electronegativity χ4.36
Hardness η2.19
Softness σ0.45
Electrophilicity index ω-4.32

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