Crystal structure and Hirshfeld surface analysis of 3-eth­oxy-1-ethyl-6-nitro­quinoxalin-2(1H)-one

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.

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

3-Ethoxy-1-ethyl-6-nitroquinoxalin-2(1H)-one

Crystal data

C12H13N3O4	F(000) = 1104
Mr = 263.25	Dx = 1.405 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 14.4848 (3) Å	Cell parameters from 9131 reflections
b = 12.5663 (2) Å	θ = 3.6–74.5°
c = 15.2708 (3) Å	µ = 0.91 mm^−1
β = 116.424 (1)°	T = 240 K
V = 2489.20 (8) Å^3	Plate, colourless
Z = 8	0.25 × 0.16 × 0.09 mm

Data collection

Bruker D8 VENTURE PHOTON 3 CPAD diffractometer	5082 independent reflections
Radiation source: INCOATEC IµS micro–focus source	4257 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.031
Detector resolution: 7.3910 pixels mm^-1	θmax = 74.6°, θmin = 3.5°
φ and ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −15→15
Tmin = 0.81, Tmax = 0.93	l = −19→19
66682 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0675P)^2 + 0.623P] where P = (Fo^2 + 2Fc^2)/3
5082 reflections	(Δ/σ)max < 0.001
355 parameters	Δρmax = 0.31 e Å^−3
2 restraints	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.58896 (9)	0.18517 (10)	0.72886 (8)	0.0684 (3)
O2	0.56752 (8)	−0.02104 (9)	0.75322 (7)	0.0577 (3)
O3	0.19338 (10)	−0.15645 (11)	0.26502 (10)	0.0782 (4)
O4	0.14323 (14)	−0.01613 (14)	0.17867 (10)	0.1109 (6)
N1	0.44938 (10)	0.18526 (10)	0.57903 (9)	0.0511 (3)
N2	0.44267 (8)	−0.03747 (10)	0.59520 (8)	0.0467 (3)
N3	0.19358 (11)	−0.06088 (12)	0.25626 (10)	0.0642 (4)
C1	0.38082 (10)	0.01493 (11)	0.50836 (9)	0.0426 (3)
C2	0.31774 (10)	−0.04604 (11)	0.42806 (10)	0.0464 (3)
H2	0.317239	−0.120587	0.432885	0.056*
C3	0.25591 (10)	0.00398 (12)	0.34124 (10)	0.0492 (3)
C4	0.25135 (11)	0.11315 (13)	0.33181 (11)	0.0541 (3)
H4	0.206429	0.145274	0.272425	0.065*
C5	0.31383 (12)	0.17440 (12)	0.41099 (11)	0.0539 (3)
H5	0.311584	0.248970	0.405576	0.065*
C6	0.38049 (10)	0.12651 (11)	0.49926 (10)	0.0450 (3)
C7	0.52019 (11)	0.13682 (13)	0.66320 (10)	0.0517 (3)
C8	0.50543 (10)	0.02007 (12)	0.66644 (10)	0.0473 (3)
C9	0.45860 (15)	0.30158 (13)	0.57188 (13)	0.0666 (4)
H9A	0.488141	0.332644	0.637598	0.080*
H9B	0.389883	0.332289	0.534364	0.080*
C10	0.52561 (17)	0.32914 (14)	0.52314 (14)	0.0766 (5)
H10A	0.497112	0.297461	0.458485	0.115*
H10B	0.594651	0.301914	0.561957	0.115*
H10C	0.528319	0.405843	0.517508	0.115*
C11	0.56054 (13)	−0.13524 (13)	0.76522 (11)	0.0605 (4)
H11A	0.579346	−0.174311	0.719964	0.073*
H11B	0.490108	−0.155018	0.752061	0.073*
C12	0.63413 (19)	−0.16070 (19)	0.86897 (13)	0.0921 (7)
H12A	0.632603	−0.236554	0.880035	0.138*
H12B	0.614122	−0.122158	0.912869	0.138*
H12C	0.703298	−0.139877	0.881165	0.138*
O5	0.41594 (10)	0.27601 (10)	0.77918 (9)	0.0750 (4)
O6	0.41831 (8)	0.47798 (9)	0.73392 (7)	0.0588 (3)
O7	0.78801 (11)	0.68361 (11)	1.19824 (10)	0.0799 (4)
O8	0.85032 (11)	0.55613 (13)	1.30161 (9)	0.0905 (5)
N4	0.54742 (11)	0.29975 (11)	0.93216 (11)	0.0677 (4)
N5	0.54324 (8)	0.51731 (9)	0.88781 (8)	0.0468 (3)
N6	0.79426 (10)	0.58951 (13)	1.21966 (10)	0.0627 (4)
C13	0.60770 (10)	0.47806 (11)	0.98025 (9)	0.0438 (3)
C14	0.66831 (10)	0.54983 (11)	1.05191 (10)	0.0461 (3)
H14	0.665103	0.622919	1.037718	0.055*
C15	0.73319 (10)	0.51310 (12)	1.14396 (10)	0.0498 (3)
C16	0.74255 (12)	0.40606 (14)	1.16725 (11)	0.0578 (4)
H16	0.789513	0.382691	1.229824	0.069*
C17	0.68202 (12)	0.33456 (13)	1.09731 (12)	0.0621 (4)
H17	0.686887	0.261628	1.112391	0.075*
C18	0.61299 (11)	0.36931 (12)	1.00359 (11)	0.0518 (3)
C19	0.47782 (11)	0.33450 (13)	0.84112 (11)	0.0564 (4)
C20	0.48407 (10)	0.45019 (12)	0.82464 (10)	0.0483 (3)
C21	0.5397 (4)	0.1885 (2)	0.9655 (3)	0.0725 (10)	0.584 (3)
H21A	0.545104	0.190628	1.031782	0.087*	0.584 (3)
H21B	0.472838	0.157386	0.921877	0.087*	0.584 (3)
C22	0.6251 (3)	0.1219 (3)	0.9644 (3)	0.0948 (10)	0.584 (3)
H22A	0.621554	0.123323	0.899417	0.142*	0.584 (3)
H22B	0.617965	0.049216	0.981755	0.142*	0.584 (3)
H22C	0.690994	0.150227	1.011130	0.142*	0.584 (3)
C21A	0.5585 (6)	0.1809 (2)	0.9319 (4)	0.0725 (10)	0.416 (3)
H21C	0.534530	0.152573	0.865601	0.087*	0.416 (3)
H21D	0.629601	0.157939	0.972557	0.087*	0.416 (3)
C22A	0.4881 (5)	0.1506 (4)	0.9761 (4)	0.0948 (10)	0.416 (3)
H22D	0.418325	0.172893	0.933020	0.142*	0.416 (3)
H22E	0.510762	0.185404	1.039032	0.142*	0.416 (3)
H22F	0.489736	0.074101	0.984864	0.142*	0.416 (3)
C23	0.41646 (13)	0.58928 (14)	0.70810 (11)	0.0630 (4)
H23A	0.481697	0.609561	0.707899	0.076*
H23B	0.405551	0.634521	0.754941	0.076*
C24	0.32870 (16)	0.60100 (19)	0.60766 (13)	0.0839 (6)
H24A	0.324461	0.674367	0.586453	0.126*
H24B	0.264740	0.581156	0.609230	0.126*
H24C	0.340219	0.555057	0.562429	0.126*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0666 (7)	0.0702 (7)	0.0516 (6)	−0.0133 (6)	0.0110 (5)	−0.0110 (5)
O2	0.0527 (6)	0.0681 (7)	0.0402 (5)	0.0037 (5)	0.0097 (4)	0.0060 (5)
O3	0.0808 (8)	0.0657 (8)	0.0680 (8)	−0.0162 (6)	0.0149 (6)	−0.0151 (6)
O4	0.1185 (12)	0.0978 (11)	0.0523 (7)	−0.0217 (9)	−0.0196 (7)	0.0053 (7)
N1	0.0575 (7)	0.0460 (6)	0.0439 (6)	−0.0005 (5)	0.0173 (5)	−0.0048 (5)
N2	0.0428 (6)	0.0522 (6)	0.0410 (6)	0.0024 (5)	0.0151 (5)	0.0053 (5)
N3	0.0571 (7)	0.0682 (9)	0.0499 (7)	−0.0110 (6)	0.0081 (6)	−0.0044 (6)
C1	0.0391 (6)	0.0471 (7)	0.0400 (6)	0.0016 (5)	0.0162 (5)	0.0023 (5)
C2	0.0431 (7)	0.0463 (7)	0.0456 (7)	−0.0025 (5)	0.0159 (6)	0.0014 (5)
C3	0.0422 (7)	0.0564 (8)	0.0417 (7)	−0.0047 (6)	0.0120 (6)	−0.0020 (6)
C4	0.0495 (7)	0.0581 (8)	0.0430 (7)	0.0032 (6)	0.0100 (6)	0.0086 (6)
C5	0.0583 (8)	0.0459 (7)	0.0497 (8)	0.0044 (6)	0.0170 (7)	0.0054 (6)
C6	0.0448 (7)	0.0469 (7)	0.0407 (7)	0.0022 (5)	0.0167 (5)	−0.0017 (5)
C7	0.0499 (7)	0.0587 (8)	0.0431 (7)	−0.0020 (6)	0.0177 (6)	−0.0057 (6)
C8	0.0420 (6)	0.0581 (8)	0.0389 (6)	0.0022 (6)	0.0154 (5)	0.0031 (6)
C9	0.0817 (11)	0.0442 (8)	0.0587 (9)	0.0015 (7)	0.0177 (8)	−0.0096 (7)
C10	0.0962 (14)	0.0537 (9)	0.0664 (11)	−0.0152 (9)	0.0242 (10)	0.0010 (8)
C11	0.0582 (9)	0.0647 (10)	0.0496 (8)	0.0100 (7)	0.0160 (7)	0.0133 (7)
C12	0.1129 (17)	0.0938 (15)	0.0472 (9)	0.0270 (13)	0.0154 (10)	0.0162 (9)
O5	0.0672 (7)	0.0703 (8)	0.0665 (7)	−0.0164 (6)	0.0108 (6)	−0.0165 (6)
O6	0.0545 (6)	0.0687 (7)	0.0395 (5)	0.0039 (5)	0.0084 (4)	−0.0010 (5)
O7	0.0814 (8)	0.0699 (8)	0.0713 (8)	−0.0128 (7)	0.0185 (7)	−0.0192 (6)
O8	0.0821 (9)	0.1119 (12)	0.0456 (6)	−0.0207 (8)	−0.0003 (6)	−0.0032 (7)
N4	0.0618 (8)	0.0444 (7)	0.0686 (9)	−0.0033 (6)	0.0035 (7)	0.0003 (6)
N5	0.0449 (6)	0.0510 (6)	0.0392 (6)	0.0030 (5)	0.0142 (5)	0.0021 (5)
N6	0.0524 (7)	0.0794 (10)	0.0474 (7)	−0.0110 (6)	0.0144 (6)	−0.0106 (6)
C13	0.0399 (6)	0.0477 (7)	0.0403 (7)	0.0019 (5)	0.0149 (5)	0.0016 (5)
C14	0.0445 (7)	0.0477 (7)	0.0438 (7)	−0.0011 (5)	0.0175 (6)	0.0002 (5)
C15	0.0420 (7)	0.0613 (9)	0.0408 (7)	−0.0039 (6)	0.0138 (6)	−0.0030 (6)
C16	0.0495 (8)	0.0668 (9)	0.0446 (7)	0.0032 (7)	0.0097 (6)	0.0087 (7)
C17	0.0602 (9)	0.0518 (8)	0.0576 (9)	0.0039 (7)	0.0111 (7)	0.0118 (7)
C18	0.0463 (7)	0.0472 (7)	0.0500 (8)	−0.0001 (6)	0.0107 (6)	0.0014 (6)
C19	0.0471 (7)	0.0573 (9)	0.0537 (8)	−0.0030 (6)	0.0125 (6)	−0.0081 (7)
C20	0.0422 (7)	0.0564 (8)	0.0413 (7)	0.0035 (6)	0.0139 (5)	−0.0013 (6)
C21	0.094 (2)	0.0477 (12)	0.063 (3)	−0.0111 (13)	0.0230 (18)	0.0014 (13)
C22	0.147 (3)	0.0596 (16)	0.0650 (16)	0.0060 (19)	0.0352 (18)	0.0036 (13)
C21A	0.094 (2)	0.0477 (12)	0.063 (3)	−0.0111 (13)	0.0230 (18)	0.0014 (13)
C22A	0.147 (3)	0.0596 (16)	0.0650 (16)	0.0060 (19)	0.0352 (18)	0.0036 (13)
C23	0.0613 (9)	0.0723 (10)	0.0449 (8)	0.0092 (8)	0.0142 (7)	0.0088 (7)
C24	0.0837 (13)	0.1014 (15)	0.0454 (9)	0.0179 (11)	0.0098 (9)	0.0116 (9)

Geometric parameters (Å, º)

O1—C7	1.2156 (18)	O8—N6	1.2234 (19)
O2—C8	1.3308 (16)	N4—C19	1.376 (2)
O2—C11	1.456 (2)	N4—C18	1.3906 (19)
O3—N3	1.2084 (19)	N4—C21A	1.503 (3)
O4—N3	1.2178 (19)	N4—C21	1.509 (3)
N1—C7	1.3789 (18)	N5—C20	1.2809 (18)
N1—C6	1.3938 (17)	N5—C13	1.3909 (16)
N1—C9	1.4762 (19)	N6—C15	1.4597 (19)
N2—C8	1.2856 (18)	C13—C14	1.3880 (19)
N2—C1	1.3920 (16)	C13—C18	1.406 (2)
N3—C3	1.4563 (18)	C14—C15	1.3771 (19)
C1—C2	1.3886 (18)	C14—H14	0.9400
C1—C6	1.4088 (19)	C15—C16	1.382 (2)
C2—C3	1.3777 (19)	C16—C17	1.372 (2)
C2—H2	0.9400	C16—H16	0.9400
C3—C4	1.378 (2)	C17—C18	1.402 (2)
C4—C5	1.378 (2)	C17—H17	0.9400
C4—H4	0.9400	C19—C20	1.485 (2)
C5—C6	1.3975 (19)	C21—C22	1.500 (5)
C5—H5	0.9400	C21—H21A	0.9800
C7—C8	1.487 (2)	C21—H21B	0.9800
C9—C10	1.503 (3)	C22—H22A	0.9700
C9—H9A	0.9800	C22—H22B	0.9700
C9—H9B	0.9800	C22—H22C	0.9700
C10—H10A	0.9700	C21A—C22A	1.500 (5)
C10—H10B	0.9700	C21A—H21C	0.9800
C10—H10C	0.9700	C21A—H21D	0.9800
C11—C12	1.499 (2)	C22A—H22D	0.9700
C11—H11A	0.9800	C22A—H22E	0.9700
C11—H11B	0.9800	C22A—H22F	0.9700
C12—H12A	0.9700	C23—C24	1.502 (2)
C12—H12B	0.9700	C23—H23A	0.9800
C12—H12C	0.9700	C23—H23B	0.9800
O5—C19	1.2181 (18)	C24—H24A	0.9700
O6—C20	1.3320 (16)	C24—H24B	0.9700
O6—C23	1.450 (2)	C24—H24C	0.9700
O7—N6	1.219 (2)
C8—O2—C11	117.00 (12)	O7—N6—O8	122.89 (15)
C7—N1—C6	121.81 (12)	O7—N6—C15	118.61 (13)
C7—N1—C9	116.86 (12)	O8—N6—C15	118.49 (15)
C6—N1—C9	120.86 (12)	C14—C13—N5	118.24 (12)
C8—N2—C1	116.94 (12)	C14—C13—C18	119.19 (12)
O3—N3—O4	122.46 (15)	N5—C13—C18	122.57 (12)
O3—N3—C3	119.25 (13)	C15—C14—C13	119.46 (13)
O4—N3—C3	118.29 (15)	C15—C14—H14	120.3
C2—C1—N2	118.15 (12)	C13—C14—H14	120.3
C2—C1—C6	119.35 (12)	C14—C15—C16	122.21 (14)
N2—C1—C6	122.50 (12)	C14—C15—N6	119.06 (14)
C3—C2—C1	119.25 (13)	C16—C15—N6	118.73 (13)
C3—C2—H2	120.4	C17—C16—C15	118.77 (14)
C1—C2—H2	120.4	C17—C16—H16	120.6
C2—C3—C4	122.36 (13)	C15—C16—H16	120.6
C2—C3—N3	118.81 (13)	C16—C17—C18	120.60 (15)
C4—C3—N3	118.83 (13)	C16—C17—H17	119.7
C3—C4—C5	118.82 (13)	C18—C17—H17	119.7
C3—C4—H4	120.6	N4—C18—C17	122.21 (14)
C5—C4—H4	120.6	N4—C18—C13	118.09 (13)
C4—C5—C6	120.52 (14)	C17—C18—C13	119.69 (13)
C4—C5—H5	119.7	O5—C19—N4	123.26 (15)
C6—C5—H5	119.7	O5—C19—C20	122.57 (15)
N1—C6—C5	122.24 (13)	N4—C19—C20	114.17 (13)
N1—C6—C1	118.12 (12)	N5—C20—O6	122.66 (14)
C5—C6—C1	119.62 (12)	N5—C20—C19	126.01 (13)
O1—C7—N1	123.01 (15)	O6—C20—C19	111.33 (12)
O1—C7—C8	122.88 (14)	C22—C21—N4	109.1 (3)
N1—C7—C8	114.10 (12)	C22—C21—H21A	109.9
N2—C8—O2	122.29 (13)	N4—C21—H21A	109.9
N2—C8—C7	125.80 (12)	C22—C21—H21B	109.9
O2—C8—C7	111.89 (12)	N4—C21—H21B	109.9
N1—C9—C10	111.37 (14)	H21A—C21—H21B	108.3
N1—C9—H9A	109.4	C21—C22—H22A	109.5
C10—C9—H9A	109.4	C21—C22—H22B	109.5
N1—C9—H9B	109.4	H22A—C22—H22B	109.5
C10—C9—H9B	109.4	C21—C22—H22C	109.5
H9A—C9—H9B	108.0	H22A—C22—H22C	109.5
C9—C10—H10A	109.5	H22B—C22—H22C	109.5
C9—C10—H10B	109.5	C22A—C21A—N4	99.0 (4)
H10A—C10—H10B	109.5	C22A—C21A—H21C	112.0
C9—C10—H10C	109.5	N4—C21A—H21C	112.0
H10A—C10—H10C	109.5	C22A—C21A—H21D	112.0
H10B—C10—H10C	109.5	N4—C21A—H21D	112.0
O2—C11—C12	106.68 (15)	H21C—C21A—H21D	109.7
O2—C11—H11A	110.4	C21A—C22A—H22D	109.5
C12—C11—H11A	110.4	C21A—C22A—H22E	109.5
O2—C11—H11B	110.4	H22D—C22A—H22E	109.5
C12—C11—H11B	110.4	C21A—C22A—H22F	109.5
H11A—C11—H11B	108.6	H22D—C22A—H22F	109.5
C11—C12—H12A	109.5	H22E—C22A—H22F	109.5
C11—C12—H12B	109.5	O6—C23—C24	106.09 (15)
H12A—C12—H12B	109.5	O6—C23—H23A	110.5
C11—C12—H12C	109.5	C24—C23—H23A	110.5
H12A—C12—H12C	109.5	O6—C23—H23B	110.5
H12B—C12—H12C	109.5	C24—C23—H23B	110.5
C20—O6—C23	116.99 (12)	H23A—C23—H23B	108.7
C19—N4—C18	122.06 (13)	C23—C24—H24A	109.5
C19—N4—C21A	110.1 (3)	C23—C24—H24B	109.5
C18—N4—C21A	126.2 (3)	H24A—C24—H24B	109.5
C19—N4—C21	120.3 (2)	C23—C24—H24C	109.5
C18—N4—C21	116.4 (2)	H24A—C24—H24C	109.5
C20—N5—C13	116.92 (12)	H24B—C24—H24C	109.5
C8—N2—C1—C2	175.40 (12)	C18—C13—C14—C15	0.7 (2)
C8—N2—C1—C6	−4.29 (19)	C13—C14—C15—C16	1.9 (2)
N2—C1—C2—C3	−179.92 (12)	C13—C14—C15—N6	−178.12 (12)
C6—C1—C2—C3	−0.21 (19)	O7—N6—C15—C14	−2.0 (2)
C1—C2—C3—C4	−2.4 (2)	O8—N6—C15—C14	178.77 (14)
C1—C2—C3—N3	177.23 (12)	O7—N6—C15—C16	178.01 (15)
O3—N3—C3—C2	3.8 (2)	O8—N6—C15—C16	−1.2 (2)
O4—N3—C3—C2	−176.32 (17)	C14—C15—C16—C17	−2.7 (2)
O3—N3—C3—C4	−176.54 (15)	N6—C15—C16—C17	177.32 (14)
O4—N3—C3—C4	3.3 (2)	C15—C16—C17—C18	0.9 (3)
C2—C3—C4—C5	2.6 (2)	C19—N4—C18—C17	178.21 (16)
N3—C3—C4—C5	−177.08 (14)	C21A—N4—C18—C17	−17.8 (4)
C3—C4—C5—C6	−0.1 (2)	C21—N4—C18—C17	11.0 (3)
C7—N1—C6—C5	−175.02 (13)	C19—N4—C18—C13	−0.8 (2)
C9—N1—C6—C5	−3.1 (2)	C21A—N4—C18—C13	163.2 (3)
C7—N1—C6—C1	3.41 (19)	C21—N4—C18—C13	−168.0 (2)
C9—N1—C6—C1	175.31 (13)	C16—C17—C18—N4	−177.29 (16)
C4—C5—C6—N1	175.95 (13)	C16—C17—C18—C13	1.7 (2)
C4—C5—C6—C1	−2.5 (2)	C14—C13—C18—N4	176.54 (13)
C2—C1—C6—N1	−175.89 (12)	N5—C13—C18—N4	−3.0 (2)
N2—C1—C6—N1	3.80 (19)	C14—C13—C18—C17	−2.5 (2)
C2—C1—C6—C5	2.6 (2)	N5—C13—C18—C17	177.98 (13)
N2—C1—C6—C5	−177.72 (12)	C18—N4—C19—O5	−176.01 (16)
C6—N1—C7—O1	170.86 (14)	C21A—N4—C19—O5	17.7 (3)
C9—N1—C7—O1	−1.3 (2)	C21—N4—C19—O5	−9.3 (3)
C6—N1—C7—C8	−8.83 (19)	C18—N4—C19—C20	3.7 (2)
C9—N1—C7—C8	178.96 (13)	C21A—N4—C19—C20	−162.6 (3)
C1—N2—C8—O2	179.26 (11)	C21—N4—C19—C20	170.4 (2)
C1—N2—C8—C7	−2.2 (2)	C13—N5—C20—O6	179.47 (12)
C11—O2—C8—N2	−0.9 (2)	C13—N5—C20—C19	0.2 (2)
C11—O2—C8—C7	−179.69 (12)	C23—O6—C20—N5	0.5 (2)
O1—C7—C8—N2	−171.07 (14)	C23—O6—C20—C19	179.92 (13)
N1—C7—C8—N2	8.6 (2)	O5—C19—C20—N5	176.16 (15)
O1—C7—C8—O2	7.6 (2)	N4—C19—C20—N5	−3.6 (2)
N1—C7—C8—O2	−172.67 (12)	O5—C19—C20—O6	−3.2 (2)
C7—N1—C9—C10	91.55 (17)	N4—C19—C20—O6	177.06 (13)
C6—N1—C9—C10	−80.74 (18)	C19—N4—C21—C22	106.9 (3)
C8—O2—C11—C12	−177.81 (14)	C18—N4—C21—C22	−85.6 (3)
C20—N5—C13—C14	−176.30 (12)	C19—N4—C21A—C22A	−98.8 (4)
C20—N5—C13—C18	3.2 (2)	C18—N4—C21A—C22A	95.6 (5)
N5—C13—C14—C15	−179.71 (12)	C20—O6—C23—C24	−173.60 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O3^i	0.98	2.59	3.250 (2)	125
C16—H16···O5^ii	0.94	2.58	3.2624 (19)	130
C22—H22A···O1	0.97	2.55	3.487 (4)	162

Symmetry codes: (i) x+1/2, −y−1/2, z+1/2; (ii) x+1/2, −y+1/2, z+1/2.

Comparison of the selected (X-ray and DFT) geometric data (Å, °)

Bonds/angles	X-ray	B3LYP/6-311G(d,p)
O1—C7	1.2156 (18)	1.2145
O2—C8	1.3308 (16)	1.3257
O2—C11	1.456 (2)	1.4490
O3—N3	1.2084 (19)	1.2236
O4—N3	1.2178 (19)	1.2254
C8—O2—C11	117.00 (12)	117.61
C7—N1—C6	121.81 (12)	122.08
C6—N1—C9	120.86 (12)	121.09
O3—N3—O4	122.46 (15)	123.09
O1—C7—N1	123.01 (15)	123.12

Calculated energies.

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 A	2.16
Electronegativity χ	4.36
Hardness η	2.19
Softness σ	0.45
Electrophilicity index ω	-4.32