Crystal structure, Hirshfeld surface analysis and density functional theory study of 1-nonyl-3-phenyl­quinoxalin-2-one

Abad, N.; Chkirate, K.; Al-Ostoot, F.H.; Van Meervelt, L.; Lahmidi, S.; Ferfra, S.; Ramli, Y.; Essassi, E.M.

doi:10.1107/S2056989021009737

Crystal structure, Hirshfeld surface analysis and density functional theory study of 1-nonyl-3-phenylquinoxalin-2-one

N. Abad, K. Chkirate, F. H. Al-Ostoot, L. Van Meervelt, S. Lahmidi, S. Ferfra, Y. Ramli and E. M. Essassi

The phenyl-quinoxaline moiety in the title compound is not planar. In the crystal, C—H

O hydrogen bonds between neighboring quinoxaline rings form chains along the a axis direction.

Keywords: crystal structure; density functional theory; quinoxaline; hydrogen bond; Hirshfeld surface analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021009737/dj2034sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989021009737/dj2034Isup3.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021009737/dj2034Isup3.cml Supplementary material

CCDC reference: 2110486

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R factor = 0.070
wR factor = 0.240
Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        4.4 Ratio
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C16 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00406 Ang.
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C13BB Check
                    C13BB       H13A
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C13BB Check
                    C13BB       H13B
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C13BB Check
                    C13BB       C14B
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C14BB Check
                    C14BB       H14A
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C14BB Check
                    C14BB       H14B
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C14BB Check
                    C14BB       C15B
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C15BB Check
                    C15BB       H15A
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C15BB Check
                    C15BB       H15B
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C13AA Check
                    C13AA       H13C
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C13AA Check
                    C13AA       H13D
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C13AA Check
                    C13AA       C14A
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C14AA Check
                    C14AA       H14C
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C14AA Check
                    C14AA       H14D
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C14AA Check
                    C14AA       C15A
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C15AA Check
                    C15AA       H15C
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C15AA Check
                    C15AA       H15D
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C15BB Check
                    C15BB       C16
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........      C15AA Check
                    C15AA       C16
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C14AA Check
                    C14AA       C13AA       C12
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C14BB Check
                    C14BB       C13BB       C12
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C14BB Check
                    C14BB       C13BB       H13A
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H13AB Check
                    H13AB       C13BB       H13B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C14BB Check
                    C14BB       C13BB       H13B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C13BB Check
                    C13BB       C14BB       H14A
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C15BB Check
                    C15BB       C14BB       H14A
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H14AB Check
                    H14AB       C14BB       H14B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C13BB Check
                    C13BB       C14BB       H14B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C15BB Check
                    C15BB       C14BB       H14B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C13BB Check
                    C13BB       C14BB       C15B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C14BB Check
                    C14BB       C15BB       H15A
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C14BB Check
                    C14BB       C15BB       H15B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H15AB Check
                    H15AB       C15BB       H15B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C14AA Check
                    C14AA       C13AA       H13C
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C14AA Check
                    C14AA       C13AA       H13D
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H13CA Check
                    H13CA       C13AA       H13D
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C13AA Check
                    C13AA       C14AA       H14C
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C15AA Check
                    C15AA       C14AA       H14C
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C15AA Check
                    C15AA       C14AA       H14D
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H14CA Check
                    H14CA       C14AA       H14D
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C13AA Check
                    C13AA       C14AA       H14D
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C13AA Check
                    C13AA       C14AA       C15A
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C14AA Check
                    C14AA       C15AA       H15C
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C14AA Check
                    C14AA       C15AA       H15D
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H15CA Check
                    H15CA       C15AA       H15D
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C13AA Check
                    C13AA       C12         C11
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C13BB Check
                    C13BB       C12         H12C
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H12CB Check
                    H12CB       C12         H12D
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C13BB Check
                    C13BB       C12         H12D
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C13AA Check
                    C13AA       C12         H12A
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C13AA Check
                    C13AA       C12         H12B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H12AA Check
                    H12AA       C12         H12B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C15BB Check
                    C15BB       C16         H16C
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C15BB Check
                    C15BB       C16         H16D
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H16CB Check
                    H16CB       C16         H16D
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C15AA Check
                    C15AA       C16         H16A
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H16AA Check
                    H16AA       C16         H16B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C15AA Check
                    C15AA       C16         H16B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C15BB Check
                    C15BB       C16         C17
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C13BB Check
                    C12         C13BB       H13A
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C13BB Check
                    C12         C13BB       H13B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C13AA Check
                    C12         C13AA       H13C
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C13AA Check
                    C12         C13AA       H13D
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C15BB Check
                    C16         C15BB       C14B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C15BB Check
                    C16         C15BB       H15A
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C15BB Check
                    C16         C15BB       H15B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C15AA Check
                    C16         C15AA       C14A
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C15AA Check
                    C16         C15AA       H15C
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      C15AA Check
                    C16         C15AA       H15D
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........      C13AA Check
                    C13AA       C14AA       C15AA       C16
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........      C13BB Check
                    C13BB       C14BB       C15BB       C16
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........      C14BB Check
                    C14BB       C15BB       C16         C17
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........      C14AA Check
                    C14AA       C15AA       C16         C17
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........      C13AA Check
                    C10         C11         C12         C13AA
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........      C13BB Check
                    C10         C11         C12         C13BB
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........      C13BB Check
                    C11         C12         C13BB       C14BB
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........      C13AA Check
                    C11         C12         C13AA       C14AA
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........      C13AA Check
                    C12         C13AA       C14AA       C15AA
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........      C13BB Check
                    C12         C13BB       C14BB       C15BB
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.596 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          9 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          8 Note
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.11 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.003 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT173_ALERT_4_G The CIF-Embedded .res File Contains DANG Records          1 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        12% Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         70 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          9 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  83 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  13 ALERT level G = General information/check it is not something unexpected

  81 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/4 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1-Nonyl-3-phenylquinoxalin-2-one top

Crystal data top

C₂₃H₂₈N₂O	Z = 2
M_r = 348.47	F(000) = 376
Triclinic, P1	D_x = 1.168 Mg m⁻³
a = 5.2353 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.5065 (5) Å	Cell parameters from 6605 reflections
c = 14.3158 (5) Å	θ = 3.0–26.4°
α = 98.045 (3)°	µ = 0.07 mm⁻¹
β = 98.327 (3)°	T = 293 K
γ = 91.255 (3)°	Block, colourless
V = 990.83 (6) Å³	0.45 × 0.3 × 0.15 mm

Data collection top

SuperNova, Single source at offset/far, Eos diffractometer	4058 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2864 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.022
Detector resolution: 15.9631 pixels mm^-1	θ_max = 26.4°, θ_min = 2.9°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2018)	k = −16→16
T_min = 0.686, T_max = 1.000	l = −17→17
20242 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.070	H-atom parameters constrained
wR(F²) = 0.240	w = 1/[σ²(F_o²) + (0.1119P)² + 0.4832P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4058 reflections	Δρ_max = 0.37 e Å⁻³
264 parameters	Δρ_min = −0.45 e Å⁻³
70 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.3177 (4)	0.43358 (13)	0.55347 (14)	0.0685 (5)
N1	0.6712 (4)	0.35716 (13)	0.61382 (14)	0.0498 (5)
C1	0.4408 (5)	0.35784 (17)	0.55355 (17)	0.0510 (5)
N2	0.4810 (4)	0.17973 (14)	0.50005 (14)	0.0527 (5)
C2	0.3592 (4)	0.26106 (16)	0.49062 (16)	0.0489 (5)
C3	0.6998 (5)	0.18102 (17)	0.56737 (17)	0.0516 (6)
C4	0.8245 (5)	0.09152 (19)	0.5763 (2)	0.0625 (7)
H4	0.755288	0.032153	0.539594	0.075*
C5	1.0489 (6)	0.0911 (2)	0.6392 (2)	0.0698 (7)
H5	1.131744	0.031553	0.644889	0.084*
C6	1.1516 (5)	0.1794 (2)	0.6940 (2)	0.0672 (7)
H6	1.305232	0.178777	0.735651	0.081*
C7	1.0310 (5)	0.2677 (2)	0.68807 (18)	0.0594 (6)
H7	1.100928	0.326025	0.726530	0.071*
C8	0.8032 (4)	0.27050 (17)	0.62436 (16)	0.0497 (5)
C9	0.7704 (5)	0.45374 (17)	0.66992 (17)	0.0547 (6)
H9A	0.711702	0.507452	0.634775	0.066*
H9B	0.957721	0.455955	0.678226	0.066*
C10	0.6832 (5)	0.47073 (19)	0.76690 (18)	0.0606 (6)
H10A	0.498084	0.479028	0.758694	0.073*
H10B	0.717777	0.412121	0.798120	0.073*
C11	0.8169 (6)	0.5614 (2)	0.8298 (2)	0.0745 (8)
H11A	0.798334	0.618437	0.795459	0.089*
H11B	0.999863	0.549819	0.843410	0.089*
C12	0.7119 (8)	0.5865 (3)	0.9237 (2)	0.0978 (11)
H12C	0.774577	0.539337	0.966060	0.117*	0.396 (11)
H12D	0.524815	0.579172	0.911703	0.117*	0.396 (11)
H12A	0.555095	0.622546	0.911469	0.117*	0.604 (11)
H12B	0.663609	0.524143	0.944183	0.117*	0.604 (11)
C13B	0.791 (3)	0.6928 (9)	0.9730 (12)	0.143 (6)	0.396 (11)
H13A	0.733512	0.738151	0.928155	0.172*	0.396 (11)
H13B	0.694988	0.706615	1.026028	0.172*	0.396 (11)
C14B	1.067 (3)	0.7193 (11)	1.0101 (13)	0.178 (8)	0.396 (11)
H14A	1.144535	0.724151	0.953271	0.214*	0.396 (11)
H14B	1.131999	0.659083	1.033095	0.214*	0.396 (11)
C15B	1.203 (5)	0.8041 (10)	1.0834 (14)	0.213 (9)	0.396 (11)
H15A	1.115971	0.809553	1.139137	0.255*	0.396 (11)
H15B	1.377951	0.784635	1.103084	0.255*	0.396 (11)
C13A	0.8860 (18)	0.6470 (6)	1.0052 (4)	0.108 (3)	0.604 (11)
H13C	0.803887	0.653364	1.062129	0.129*	0.604 (11)
H13D	1.046676	0.613550	1.018024	0.129*	0.604 (11)
C14A	0.9394 (19)	0.7469 (5)	0.9806 (5)	0.109 (3)	0.604 (11)
H14C	0.778583	0.778877	0.963392	0.130*	0.604 (11)
H14D	1.033828	0.741313	0.926736	0.130*	0.604 (11)
C15A	1.095 (3)	0.8071 (7)	1.0650 (5)	0.151 (4)	0.604 (11)
H15C	0.983493	0.820608	1.113487	0.182*	0.604 (11)
H15D	1.229528	0.765333	1.089666	0.182*	0.604 (11)
C16	1.2192 (15)	0.9031 (5)	1.0549 (5)	0.208 (3)
H16C	1.047455	0.927886	1.040740	0.250*	0.396 (11)
H16D	1.302078	0.900230	0.998269	0.250*	0.396 (11)
H16A	1.331550	0.888114	1.006973	0.250*	0.604 (11)
H16B	1.083193	0.942764	1.027665	0.250*	0.604 (11)
C17	1.3710 (9)	0.9691 (3)	1.1345 (4)	0.1294 (16)
H17A	1.353016	1.037431	1.124155	0.194*
H17B	1.549689	0.953042	1.138569	0.194*
H17C	1.309895	0.959940	1.192911	0.194*
C18	0.1379 (5)	0.25620 (17)	0.41263 (17)	0.0517 (6)
C19	0.1175 (6)	0.1751 (2)	0.33936 (19)	0.0663 (7)
H19	0.242243	0.127165	0.340750	0.080*
C20	−0.0844 (6)	0.1652 (2)	0.2653 (2)	0.0780 (8)
H20	−0.094842	0.110612	0.217213	0.094*
C21	−0.2709 (6)	0.2351 (2)	0.2615 (2)	0.0749 (8)
H21	−0.408785	0.227544	0.211843	0.090*
C22	−0.2513 (5)	0.3164 (2)	0.3319 (2)	0.0680 (7)
H22	−0.375143	0.364646	0.328908	0.082*
C23	−0.0503 (5)	0.32754 (19)	0.40714 (19)	0.0574 (6)
H23	−0.040380	0.382880	0.454350	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0726 (11)	0.0453 (9)	0.0818 (13)	0.0079 (8)	0.0004 (9)	−0.0005 (8)
N1	0.0560 (11)	0.0410 (10)	0.0511 (11)	−0.0013 (8)	0.0092 (9)	0.0018 (8)
C1	0.0567 (13)	0.0449 (12)	0.0511 (13)	0.0017 (10)	0.0094 (10)	0.0046 (10)
N2	0.0590 (11)	0.0431 (10)	0.0556 (11)	0.0006 (8)	0.0100 (9)	0.0046 (8)
C2	0.0544 (12)	0.0427 (11)	0.0506 (12)	−0.0014 (9)	0.0124 (10)	0.0058 (9)
C3	0.0596 (13)	0.0458 (12)	0.0503 (13)	0.0015 (10)	0.0110 (10)	0.0071 (10)
C4	0.0740 (16)	0.0466 (13)	0.0672 (16)	0.0068 (12)	0.0115 (13)	0.0079 (11)
C5	0.0749 (17)	0.0602 (16)	0.0772 (18)	0.0160 (13)	0.0096 (14)	0.0203 (14)
C6	0.0635 (15)	0.0762 (18)	0.0627 (16)	0.0087 (13)	0.0034 (12)	0.0179 (13)
C7	0.0627 (14)	0.0593 (15)	0.0545 (14)	0.0002 (11)	0.0060 (11)	0.0058 (11)
C8	0.0567 (13)	0.0466 (12)	0.0480 (12)	0.0014 (10)	0.0143 (10)	0.0083 (9)
C9	0.0591 (13)	0.0446 (12)	0.0574 (14)	−0.0047 (10)	0.0057 (11)	0.0014 (10)
C10	0.0643 (15)	0.0564 (14)	0.0583 (15)	−0.0017 (11)	0.0083 (12)	0.0000 (11)
C11	0.0707 (17)	0.0774 (18)	0.0667 (16)	−0.0048 (14)	0.0051 (13)	−0.0135 (14)
C12	0.110 (3)	0.101 (2)	0.075 (2)	0.001 (2)	0.0198 (18)	−0.0184 (18)
C13B	0.185 (12)	0.124 (9)	0.100 (11)	−0.017 (9)	0.017 (8)	−0.049 (8)
C14B	0.234 (15)	0.157 (11)	0.116 (11)	−0.097 (12)	−0.048 (11)	0.019 (9)
C15B	0.204 (19)	0.152 (8)	0.249 (18)	−0.094 (11)	0.037 (13)	−0.073 (8)
C13A	0.143 (6)	0.120 (5)	0.054 (3)	−0.002 (4)	0.009 (3)	−0.004 (3)
C14A	0.128 (7)	0.119 (5)	0.067 (4)	−0.024 (4)	0.009 (4)	−0.015 (3)
C15A	0.192 (11)	0.174 (7)	0.070 (4)	−0.062 (6)	0.028 (5)	−0.047 (4)
C16	0.213 (7)	0.174 (5)	0.206 (7)	−0.081 (5)	0.012 (5)	−0.051 (5)
C17	0.123 (3)	0.099 (3)	0.146 (4)	−0.008 (2)	−0.013 (3)	−0.015 (3)
C18	0.0560 (13)	0.0455 (12)	0.0544 (13)	−0.0054 (10)	0.0102 (10)	0.0089 (10)
C19	0.0733 (17)	0.0538 (14)	0.0655 (16)	0.0023 (12)	−0.0016 (13)	−0.0008 (12)
C20	0.086 (2)	0.0679 (18)	0.0694 (18)	−0.0039 (15)	−0.0073 (15)	−0.0054 (14)
C21	0.0684 (17)	0.081 (2)	0.0702 (18)	−0.0068 (15)	−0.0100 (14)	0.0153 (15)
C22	0.0617 (15)	0.0711 (17)	0.0718 (17)	0.0044 (13)	0.0051 (13)	0.0174 (14)
C23	0.0570 (13)	0.0554 (13)	0.0616 (14)	−0.0001 (11)	0.0122 (11)	0.0114 (11)

Geometric parameters (Å, º) top

O1—C1	1.221 (3)	C7—C8	1.397 (3)
C13Bb—H13A	0.9700	C9—H9A	0.9700
C13Bb—H13B	0.9700	C9—H9B	0.9700
C13Bb—C14B	1.482 (10)	C9—C10	1.512 (3)
C14Bb—H14A	0.9700	C10—H10A	0.9700
C14Bb—H14B	0.9700	C10—H10B	0.9700
C14Bb—C15B	1.527 (9)	C10—C11	1.507 (4)
C15Bb—H15A	0.9700	C11—H11A	0.9700
C15Bb—H15B	0.9700	C11—H11B	0.9700
C13Aa—H13C	0.9700	C11—C12	1.523 (4)
C13Aa—H13D	0.9700	C12—H12C	0.9700
C13Aa—C14A	1.472 (8)	C12—H12D	0.9700
C14Aa—H14C	0.9700	C12—H12A	0.9700
C14Aa—H14D	0.9700	C12—H12B	0.9700
C14Aa—C15A	1.481 (7)	C12—C13B	1.528 (9)
C15Aa—H15C	0.9700	C12—C13A	1.500 (6)
C15Aa—H15D	0.9700	C16—H16C	0.9700
C15Bb—C16	1.456 (10)	C16—H16D	0.9700
C15Aa—C16	1.473 (5)	C16—H16A	0.9700
N1—C1	1.379 (3)	C16—H16B	0.9700
N1—C8	1.387 (3)	C16—C17	1.466 (7)
N1—C9	1.474 (3)	C17—H17A	0.9600
C1—C2	1.496 (3)	C17—H17B	0.9600
N2—C2	1.296 (3)	C17—H17C	0.9600
N2—C3	1.384 (3)	C18—C19	1.397 (3)
C2—C18	1.481 (3)	C18—C23	1.395 (3)
C3—C4	1.399 (3)	C19—H19	0.9300
C3—C8	1.410 (3)	C19—C20	1.375 (4)
C4—H4	0.9300	C20—H20	0.9300
C4—C5	1.373 (4)	C20—C21	1.374 (4)
C5—H5	0.9300	C21—H21	0.9300
C5—C6	1.385 (4)	C21—C22	1.374 (4)
C6—H6	0.9300	C22—H22	0.9300
C6—C7	1.369 (4)	C22—C23	1.382 (4)
C7—H7	0.9300	C23—H23	0.9300

C1—N1—C8	122.74 (19)	C15Bb—C16—C17	107.4 (8)
C14Aa—C13Aa—C12	109.4 (6)	N1—C8—C7	123.5 (2)
C14Bb—C13Bb—C12	119.6 (10)	C7—C8—C3	118.9 (2)
C14Bb—C13Bb—H13A	107.4	N1—C9—H9A	109.1
H13Ab—C13Bb—H13B	106.9	N1—C9—H9B	109.1
C14Bb—C13Bb—H13B	107.4	N1—C9—C10	112.61 (19)
C13Bb—C14Bb—H14A	104.0	H9A—C9—H9B	107.8
C1—N1—C9	116.64 (19)	C10—C9—H9A	109.1
C8—N1—C9	120.60 (19)	C10—C9—H9B	109.1
O1—C1—N1	120.6 (2)	C9—C10—H10A	109.1
O1—C1—C2	124.1 (2)	C9—C10—H10B	109.1
C15Bb—C14Bb—H14A	104.0	H10A—C10—H10B	107.8
H14Ab—C14Bb—H14B	105.4	C11—C10—C9	112.5 (2)
C13Bb—C14Bb—H14B	104.0	C11—C10—H10A	109.1
C15Bb—C14Bb—H14B	104.0	C11—C10—H10B	109.1
C13Bb—C14Bb—C15B	133.0 (17)	C10—C11—H11A	108.9
C14Bb—C15Bb—H15A	107.9	C10—C11—H11B	108.9
C14Bb—C15Bb—H15B	107.9	C10—C11—C12	113.5 (3)
H15Ab—C15Bb—H15B	107.2	H11A—C11—H11B	107.7
N1—C1—C2	115.22 (19)	C12—C11—H11A	108.9
C2—N2—C3	120.3 (2)	C12—C11—H11B	108.9
N2—C2—C1	122.0 (2)	C11—C12—H12C	109.1
N2—C2—C18	117.6 (2)	C11—C12—H12D	109.1
C18—C2—C1	120.4 (2)	C11—C12—H12A	107.9
N2—C3—C4	118.7 (2)	C11—C12—H12B	107.9
N2—C3—C8	121.6 (2)	C11—C12—C13B	112.6 (8)
C4—C3—C8	119.7 (2)	C17—C16—C15A	123.6 (7)
C3—C4—H4	119.9	C17—C16—H16C	110.2
C5—C4—C3	120.2 (2)	C12—C13Bb—H13A	107.4
C5—C4—H4	119.9	C12—C13Bb—H13B	107.4
C14Aa—C13Aa—H13C	109.8	C12—C13Aa—H13C	109.8
C14Aa—C13Aa—H13D	109.8	C12—C13Aa—H13D	109.8
H13Ca—C13Aa—H13D	108.2	C16—C15Bb—C14B	117.8 (12)
C13Aa—C14Aa—H14C	110.1	C17—C16—H16D	110.2
C15Aa—C14Aa—H14C	110.1	C17—C16—H16A	106.4
C15Aa—C14Aa—H14D	110.1	C17—C16—H16B	106.4
H14Ca—C14Aa—H14D	108.4	C16—C17—H17A	109.5
C13Aa—C14Aa—H14D	110.1	C16—C17—H17B	109.5
C13Aa—C14Aa—C15A	108.0 (6)	C16—C17—H17C	109.5
C14Aa—C15Aa—H15C	107.4	H17A—C17—H17B	109.5
C14Aa—C15Aa—H15D	107.4	H17A—C17—H17C	109.5
C4—C5—H5	120.1	H17B—C17—H17C	109.5
C4—C5—C6	119.9 (2)	C19—C18—C2	117.8 (2)
C6—C5—H5	120.1	C23—C18—C2	124.4 (2)
C5—C6—H6	119.4	C23—C18—C19	117.9 (2)
C7—C6—C5	121.2 (3)	C18—C19—H19	119.5
C7—C6—H6	119.4	C20—C19—C18	120.9 (3)
C6—C7—H7	119.9	C20—C19—H19	119.5
C6—C7—C8	120.2 (2)	C19—C20—H20	119.7
C8—C7—H7	119.9	C21—C20—C19	120.6 (3)
N1—C8—C3	117.6 (2)	C21—C20—H20	119.7
H15Ca—C15Aa—H15D	107.0	C20—C21—H21	120.4
C13Aa—C12—C11	117.4 (5)	C22—C21—C20	119.3 (3)
C13Bb—C12—H12C	109.1	C22—C21—H21	120.4
H12Cb—C12—H12D	107.8	C21—C22—H22	119.5
C13Bb—C12—H12D	109.1	C21—C22—C23	121.0 (3)
C13Aa—C12—H12A	107.9	C23—C22—H22	119.5
C13Aa—C12—H12B	107.9	C18—C23—H23	119.8
H12Aa—C12—H12B	107.2	C22—C23—C18	120.3 (3)
C15Bb—C16—H16C	110.2	C22—C23—H23	119.8
C15Bb—C16—H16D	110.2	C16—C15Bb—H15A	107.9
H16Cb—C16—H16D	108.5	C16—C15Bb—H15B	107.9
C15Aa—C16—H16A	106.4	C16—C15Aa—C14A	119.5 (7)
H16Aa—C16—H16B	106.5	C16—C15Aa—H15C	107.4
C15Aa—C16—H16B	106.4	C16—C15Aa—H15D	107.4

C13Aa—C14Aa—C15Aa—C16	168.0 (12)	C4—C3—C8—C7	0.7 (4)
C13Bb—C14Bb—C15Bb—C16	−76 (3)	C4—C5—C6—C7	1.1 (4)
C14Bb—C15Bb—C16—C17	−176.5 (18)	C5—C6—C7—C8	−1.4 (4)
C14Aa—C15Aa—C16—C17	178.4 (9)	C6—C7—C8—N1	−179.5 (2)
O1—C1—C2—N2	−172.5 (2)	C6—C7—C8—C3	0.5 (4)
O1—C1—C2—C18	9.4 (4)	C8—N1—C1—O1	172.5 (2)
N1—C1—C2—N2	7.6 (3)	C8—N1—C1—C2	−7.6 (3)
N1—C1—C2—C18	−170.52 (19)	C8—N1—C9—C10	−86.1 (3)
N1—C9—C10—C11	171.1 (2)	C8—C3—C4—C5	−1.1 (4)
C1—N1—C8—C3	2.8 (3)	C9—N1—C1—O1	−5.8 (3)
C1—N1—C8—C7	−177.2 (2)	C9—N1—C1—C2	174.13 (19)
C1—N1—C9—C10	92.3 (3)	C9—N1—C8—C3	−179.0 (2)
C1—C2—C18—C19	160.9 (2)	C9—N1—C8—C7	1.0 (3)
C1—C2—C18—C23	−18.6 (3)	C9—C10—C11—C12	173.8 (3)
N2—C2—C18—C19	−17.3 (3)	C10—C11—C12—C13Aa	157.2 (5)
N2—C2—C18—C23	163.2 (2)	C10—C11—C12—C13Bb	−163.5 (7)
N2—C3—C4—C5	176.9 (2)	C11—C12—C13Bb—C14Bb	−66.5 (19)
N2—C3—C8—N1	2.9 (3)	C11—C12—C13Aa—C14Aa	64.2 (9)
N2—C3—C8—C7	−177.2 (2)	C12—C13Aa—C14Aa—C15Aa	175.8 (8)
C2—N2—C3—C4	179.2 (2)	C12—C13Bb—C14Bb—C15Bb	−160.7 (14)
C2—N2—C3—C8	−2.8 (3)	C18—C19—C20—C21	0.1 (5)
C2—C18—C19—C20	179.3 (3)	C19—C18—C23—C22	1.0 (4)
C2—C18—C23—C22	−179.5 (2)	C19—C20—C21—C22	1.1 (5)
C3—N2—C2—C1	−2.5 (3)	C20—C21—C22—C23	−1.3 (5)
C3—N2—C2—C18	175.63 (19)	C21—C22—C23—C18	0.3 (4)
C3—C4—C5—C6	0.2 (4)	C23—C18—C19—C20	−1.2 (4)
C4—C3—C8—N1	−179.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···N2	0.93	2.44	2.758 (3)	100
C23—H23···O1	0.93	2.21	2.832 (3)	123

Comparison (X-ray and density functional theory) of selected bond lengths and angles (Å, °) top

	X-ray	B3LYP/6–311G(d,p)
O1—C1	1.221 (3)	1.2236
N1—C1	1.379 (3)	1.3975
N1—C8	1.387 (3)	1.3892
N1—C9	1.474 (3)	1.4735
N2—C2	1.296 (3)	1.299
N2—C3	1.384 (3)	1.3723
C2—C18	1.481 (3)	1.4862
C1—N1—C8	122.74 (19)	122.5778
C1—N1—C9	116.64 (19)	116.1328
C8—N1—C9	120.60 (19)	121.2682
O1—C1—N1	120.6 (2)	120.2255
O1—C1—C2	124.1 (2)	124.5602
N1—C1—C2	115.22 (19)	115.2104
C2—N2—C3	120.3 (2)	120.949
N2—C2—C1	122.0 (2)	121.844
N2—C2—C18	117.6 (2)	117.4937
N2—C3—C4	118.7 (2)	118.5343
N2—C3—C8	121.6 (2)	121.9008
N1—C8—C3	117.6 (2)	117.4153
N1—C8—C7	123.5 (2)	123.4308
N1—C9—C10	112.61 (19)	112.9655

Calculated energies top

Molecular Energy	Compound (I)
Total Energy, TE (eV)	-29343.5617
E_HOMO (eV)	-6,1155
E_LUMO (eV)	-2,2251
Gap, ΔE (eV)	3.8904
Dipole moment, µ (Debye)	3.0783
Ionization potential, I (eV)	6.1155
Electron affinity, A	2.2251
Electronegativity, χ	4.1703
Hardness, η	1.9452
Electrophilicity index, ω	4.4703
Softness, σ	0.5141
Fraction of electron transferred, ΔN	0.7274

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Crystal structure, Hirshfeld surface analysis and density functional theory study of 1-nonyl-3-phenyl­quinoxalin-2-one

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Crystal structure, Hirshfeld surface analysis and density functional theory study of 1-nonyl-3-phenylquinoxalin-2-one