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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 3| Part 3| March 2018| x180390
https://doi.org/10.1107/S2414314618003905

1-Benzyl-3-methyl­quinoxalin-2(1H)-one

CROSSMARK_Color_square_no_text.svg
Youssef Ramli,a Youness El Bakri,b* L'houssaine El Ghayati,b El Mokhtar Essassib and Joel T. Maguec

aLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, University Mohammed V, Rabat, Morocco, bLaboratoire de Chimie Organique Hétérocyclique, Centre de Recherche des Sciences des médicaments, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, and cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: yns.elbakri@gmail.com

Edited by J. Simpson, University of Otago, New Zealand (Received 2 March 2018; accepted 6 March 2018; online 9 March 2018)

The asymmetric unit of the title compound, C16H14N2O, contains three independent mol­ecules differing primarily in the orientations of the benzyl groups. Each independent mol­ecule forms inversion related dimers via offset π-stacking inter­actions. For two of these dimers, stacks are formed approximately along the a-axis direction by a combinations of C—H⋯N and C—H⋯π(ring) contacts, in addition to the offset π-stacking inter­actions. The third set of dimers are also stacked in the same direction but only by pairwise C—H⋯N hydrogen bonds.

CCDC reference: 1827953

Similar articles
3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Quinoxaline derivatives have a special place in medicinal chemistry and are commonly present in the bioactive mol­ecules used in many therapeutic areas (Kour et al., 2013[Kour, H., Paul, S., Singh, P. P., Gupta, M. & Gupta, R. (2013). Tetrahedron Lett. 54, 761-764.]). Compounds containing the quinoxaline moiety show a wide range of biological activities including anti-inflammatory, analgesic, and anti­depressant effects. They also demonstrate anti­fungal, anti­bacterial, anti­malarial, anti­tubercular, anti­cancer, anti­diabetic, anti­convulsant, anti­anxiety, and metal-binding properties (Rohde et al., 2016[Rohde, K. H., Michaels, H. A. & Nefzi, A. (2016). Bioorg. Med. Chem. Lett. 26, 2206-2209.]; Wang et al., 2007[Wang, H., Earley, W. G., Lewis, R. M., Srivastava, R. R., Zych, A. J., Jenkins, D. M. & Fairfax, D. J. (2007). Tetrahedron Lett. 48, 3043-3046.]; Bérubé et al., 2015[Bérubé, C., Cardinal, S., Boudreault, P., Barbeau, X., Delcey, N., Giguère, M., Gleeton, D. & Voyer, N. (2015). Tetrahedron, 71, 8077-8084.]; Ramli & Essassi, 2015[Ramli, Y. & Essassi, E. M. (2015). Advances in Chemistry Research, Vol. 27, edited by James C. Taylor, pp. 109-160. Hauppauge: Nova Science Publishers.]). In light of the above and as a contin­uation of our work on the synthesis of quinoxaline-2-thione derivatives in order to evaluate their pharmacological activity (Ramli et al., 2011[Ramli, Y., Moussaif, A., Zouihri, H., Bourichi, H. & Essassi, E. M. (2011). Acta Cryst. E67, o1374.], 2013[Ramli, Y., Karrouchi, K., Essassi, E. M. & El Ammari, L. (2013). Acta Cryst. E69, o1320-o1321.], 2017[Ramli, Y., Missioui, M., El Fal, M., Ouhcine, M., Essassi, E. M. & Mague, J. T. (2017). IUCrData, 2, x171424.]; Caleb et al., 2016[Caleb, A. A., Ramli, Y., Benabdelkame, H., Bouhfid, R., Es-Safi, N., Kandri Rodi, Y., Essassi, E. M. & Banoub, J. (2016). J. Marocain Chim. Heterocycl. 15, 109-123.]), the title compound (Fig. 1[link]) was synthesized and its structure is reported here.

[Figure 1]
Figure 1
The asymmetric unit with numbering scheme and 50% probability ellipsoids. C—H⋯O and C—H⋯π hydrogen bonds are drawn as black and green dashed lines, respectively.

The asymmetric unit of the title compound (Fig. 1[link]) consists of three independent mol­ecules differing primarily in the orientations of the benzyl group. Thus the C1—N2—C10—C11, the C17—N4—C26—C27 and the C33—N6—C42—C43 torsion angles are, respectively, 75.76 (13), 76.68 (13) and −82.29 (13)°.

In the crystal, each independent mol­ecule forms a stack, with each stack oriented approximately along the a-axis direction (Fig. 2[link]). The O1- and O2-containing mol­ecules form head-to-tail inversion dimers through offset π-stacking inter­actions. For the O1 mol­ecule, the centroid–centroid distance between the C1–C6 and C1/N2/C8/C7/N1/C6 rings is 3.4250 (7) Å. These dimers are further inter­connected by inversion-related C16—H16⋯N1 hydrogen bonds together with pairwise C9—H9C⋯Cg2 contacts, Table 1[link]. These impose additional offset π-stacking inter­actions between the alternating C1/N2/C8/C7/N1/C6 rings [centroid–centroid distance = 3.7405 (7) Å; Fig. 3[link] (left side)]. A closely similar stacking motif is found for the O2-containing mol­ecules. However the centroid–centroid distance in the dimer [3.4734 (7) Å] is slightly longer, as are the comparable C25—H25C⋯Cg6 and C34—H34⋯N3 distances [Table 1[link] and Fig. 2[link] (right side)]. The additional centroid–centroid distance between the two C17/C22/N3/C23/C24/N4 rings is also longer at 3.8725 (7) Å. Finally, for the O3-containing mol­ecules, dimers are formed with a centroid–centroid distance between the C33–C38 and C33/C38/N5/C39/C40/N6 rings of 3.4811 (7) Å [Fig. 2[link] (center)]. These dimers are connected only by pairwise C44—H44⋯N5 hydrogen bonds (Table 1[link]) with no additional C—H⋯π(ring) or π–π contacts. Stacks of O1- and O2-containing mol­ecules are linked by C19—H19⋯O1 hydrogen bonds while stacks of the O3-containing mol­ecules are connected to the others by C12—H12⋯O3 and C34—H34⋯O2 hydrogen bonds, respectively (Table 1[link] and Fig. 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg3, Cg6, Cg7 and Cg11 are the centroids of the C1–C6, C11–C16, C17–C22, C27–C32 and C43–C48 benzene rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C3—H3⋯Cg7i 1.002 (13) 2.867 (13) 3.6440 (13) 134.8 (11)
C9—H9C⋯Cg2ii 0.986 (16) 2.746 (13) 3.4470 (14) 128.4 (13)
C12—H12⋯O3 0.999 (15) 2.429 (14) 3.2448 (16) 138.5 (10)
C13—H13⋯Cg11 0.961 (16) 2.718 (19) 3.5058 (17) 139.8 (13)
C16—H16⋯N1ii 0.948 (14) 2.457 (15) 3.3430 (16) 155.5 (11)
C19—H19⋯O1iii 0.953 (13) 2.553 (14) 3.5016 (14) 174.1 (11)
C25—H25C⋯Cg6iv 1.000 (16) 2.835 (15) 3.4591 (14) 121.3 (12)
C28—H28⋯N3iv 0.990 (13) 2.538 (14) 3.4672 (16) 156.3 (10)
C30—H30⋯Cg3i 1.008 (14) 2.636 (16) 3.5668 (15) 153.9 (12)
C34—H34⋯O2 0.976 (14) 2.575 (14) 3.4126 (15) 144.0 (11)
C44—H44⋯N5v 0.988 (13) 2.490 (13) 3.3333 (15) 143.1 (10)
Symmetry codes: (i) -x+1, -y, -z; (ii) -x, -y, -z+1; (iii) x, y, z-1; (iv) -x+2, -y+1, -z; (v) -x+1, -y+1, -z+1.
[Figure 2]
Figure 2
Packing viewed along the a-axis direction with hydrogen bonds and C—H⋯π(ring) inter­actions depicted as in Fig. 2[link]. [Symmetry code: (viii) x + 1, y, z + 1.]
[Figure 3]
Figure 3
View of the inter­molecular inter­actions. C—H⋯O and C—H⋯N hydrogen bonds are shown, respectively, as black and pink dashed lines while π-stacking and C—H⋯π(ring) inter­actions are shown, respectively, by orange and green dashed lines. [Symmetry codes: (ii) −x, −y, −z + 1; (iv) −x + 2, −y + 1, −z; (vi) −x + 1, −y, −z + 1; (vii) −x + 1, −y + 1, −z; (viii) x + 1, y, z + 1.]

Synthesis and crystallization

To a solution of 3-methyl-quinoxalin-2(1H)-one (0.5 g, 3 mmol) in N,N-di­methyl­formamide (20 ml) were added benzyl chloride (0.35 ml, 3 mmol), potassium carbonate (0.43 g, 3 mmol) and a catalytic qu­antity of tetra-n-butyl­ammonium iodide. The mixture was stirred at room temperature for 48 h. The solution was filtered and the solvent removed under reduced pressure. The residue was crystallized from ethanol to afford the title compound as colourless crystals.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C16H14N2O
Mr 250.29
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 100
a, b, c (Å) 7.3502 (4), 17.3508 (10), 17.9449 (10)
α, β, γ (°) 118.226 (1), 100.042 (1), 92.294 (1)
V (Å3) 1965.63 (19)
Z 6
Radiation type Mo Kα
μ (mm−1) 0.08
Crystal size (mm) 0.33 × 0.27 × 0.24
 
Data collection
Diffractometer Bruker SMART APEX CCD
Absorption correction Multi-scan (SADABS; Bruker, 2016[Bruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.88, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections 36858, 9752, 7343
Rint 0.032
(sin θ/λ)max (Å−1) 0.669
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.124, 1.04
No. of reflections 9752
No. of parameters 682
H-atom treatment All H-atom parameters refined
Δρmax, Δρmin (e Å−3) 0.40, −0.19
Computer programs: APEX3 and SAINT (Bruker, 2016[Bruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2016 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data

CCDC reference: 1827953

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314618003905/sj4167sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618003905/sj4167Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618003905/sj4167Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314618003905/sj4167Isup4.cml

checkCIF report


Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

1-Benzyl-3-methyl-quinoxalin-2(1H)-one top
Crystal data top
C16H14N2OZ = 6
Mr = 250.29F(000) = 792
Triclinic, P1Dx = 1.269 Mg m−3
a = 7.3502 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 17.3508 (10) ÅCell parameters from 9979 reflections
c = 17.9449 (10) Åθ = 2.3–28.4°
α = 118.226 (1)°µ = 0.08 mm−1
β = 100.042 (1)°T = 100 K
γ = 92.294 (1)°Block, colourless
V = 1965.63 (19) Å30.33 × 0.27 × 0.24 mm
Data collection top
Bruker SMART APEX CCD
diffractometer		9752 independent reflections
Radiation source: fine-focus sealed tube7343 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 8.3333 pixels mm-1θmax = 28.4°, θmin = 2.3°
φ and ω scansh = −9→9
Absorption correction: multi-scan
(SADABS; Bruker, 2016)		k = −23→23
Tmin = 0.88, Tmax = 0.98l = −23→23
36858 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: difference Fourier map
wR(F2) = 0.124All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.079P)2]
where P = (Fo2 + 2Fc2)/3
9752 reflections(Δ/σ)max < 0.001
682 parametersΔρmax = 0.40 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = -30.00 and 210.00°. The scan time was 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.25912 (12)0.20951 (5)0.59094 (5)0.0277 (2)
N10.21470 (13)−0.00884 (6)0.56016 (6)0.0194 (2)
N20.29459 (13)0.08246 (6)0.47301 (6)0.0195 (2)
C10.28682 (15)−0.00957 (7)0.43184 (7)0.0179 (2)
C20.31828 (16)−0.05831 (8)0.34823 (7)0.0215 (2)
H20.3438 (19)−0.0299 (8)0.3147 (9)0.029 (4)*
C30.31140 (16)−0.14907 (8)0.31127 (7)0.0237 (2)
H30.3302 (18)−0.1825 (8)0.2505 (8)0.026 (3)*
C40.27393 (16)−0.19281 (7)0.35604 (7)0.0233 (2)
H40.2685 (18)−0.2559 (9)0.3295 (8)0.025 (3)*
C50.23991 (16)−0.14547 (7)0.43800 (7)0.0208 (2)
H50.2113 (19)−0.1747 (9)0.4715 (9)0.029 (3)*
C60.24551 (15)−0.05360 (7)0.47658 (7)0.0184 (2)
C70.22057 (15)0.07611 (7)0.59656 (7)0.0189 (2)
C80.25818 (15)0.12892 (7)0.55450 (7)0.0202 (2)
C90.19308 (18)0.12631 (8)0.68734 (8)0.0245 (3)
H9A0.306 (3)0.1689 (10)0.7257 (11)0.053 (5)*
H9B0.168 (2)0.0877 (10)0.7109 (10)0.038 (4)*
H9C0.089 (2)0.1611 (10)0.6900 (10)0.050 (5)*
C100.35018 (17)0.13201 (8)0.43105 (8)0.0236 (2)
H10A0.4637 (19)0.1114 (8)0.4100 (8)0.026 (3)*
H10B0.3824 (19)0.1958 (9)0.4787 (9)0.027 (3)*
C110.20033 (17)0.12470 (7)0.35751 (7)0.0217 (2)
C120.25335 (19)0.14397 (8)0.29634 (8)0.0269 (3)
H120.388 (2)0.1614 (9)0.3015 (9)0.031 (4)*
C130.1197 (2)0.14019 (8)0.22947 (8)0.0309 (3)
H130.157 (2)0.1535 (10)0.1877 (10)0.042 (4)*
C14−0.0673 (2)0.11708 (8)0.22232 (8)0.0310 (3)
H14−0.1662 (19)0.1130 (9)0.1739 (9)0.030 (4)*
C15−0.12054 (19)0.09877 (8)0.28310 (8)0.0299 (3)
H15−0.256 (2)0.0797 (9)0.2770 (10)0.039 (4)*
C160.01263 (17)0.10252 (8)0.35061 (8)0.0250 (3)
H16−0.0264 (19)0.0896 (9)0.3916 (9)0.031 (4)*
O20.83756 (12)0.44828 (6)0.14776 (5)0.0288 (2)
N30.82391 (13)0.56950 (6)0.03367 (6)0.0203 (2)
N40.68101 (13)0.40490 (6)0.00926 (6)0.0183 (2)
C170.64388 (15)0.42244 (7)−0.05980 (7)0.0166 (2)
C180.53684 (15)0.36034 (7)−0.14181 (7)0.0203 (2)
H180.4877 (19)0.3022 (9)−0.1507 (8)0.029 (4)*
C190.50247 (16)0.38126 (8)−0.20784 (7)0.0226 (2)
H190.4289 (19)0.3372 (9)−0.2623 (9)0.027 (3)*
C200.57138 (16)0.46423 (8)−0.19377 (7)0.0233 (2)
H200.5407 (19)0.4772 (8)−0.2406 (9)0.029 (4)*
C210.67822 (17)0.52534 (8)−0.11371 (7)0.0219 (2)
H210.7310 (19)0.5837 (9)−0.1041 (8)0.026 (3)*
C220.71649 (15)0.50512 (7)−0.04612 (7)0.0176 (2)
C230.86029 (15)0.55100 (7)0.09630 (7)0.0200 (2)
C240.79521 (15)0.46502 (7)0.08829 (7)0.0197 (2)
C250.97279 (18)0.61937 (8)0.18262 (8)0.0258 (3)
H25A0.900 (2)0.6396 (9)0.2251 (9)0.036 (4)*
H25B1.013 (2)0.6728 (10)0.1804 (10)0.045 (4)*
H25C1.077 (2)0.5944 (10)0.2035 (10)0.044 (4)*
C260.59944 (17)0.32168 (7)−0.00011 (8)0.0223 (2)
H26A0.605 (2)0.3317 (9)0.0589 (10)0.033 (4)*
H26B0.4654 (19)0.3103 (8)−0.0276 (8)0.023 (3)*
C270.69508 (17)0.24355 (7)−0.05122 (7)0.0215 (2)
C280.87161 (17)0.25453 (8)−0.06534 (7)0.0231 (2)
H280.9364 (19)0.3148 (9)−0.0435 (8)0.026 (3)*
C290.95776 (19)0.18102 (8)−0.10981 (7)0.0273 (3)
H291.083 (2)0.1914 (9)−0.1200 (9)0.033 (4)*
C300.8698 (2)0.09670 (8)−0.13975 (8)0.0329 (3)
H300.932 (2)0.0436 (9)−0.1720 (9)0.038 (4)*
C310.6934 (2)0.08534 (9)−0.12627 (9)0.0385 (3)
H310.634 (2)0.0259 (11)−0.1465 (10)0.051 (5)*
C320.6049 (2)0.15839 (8)−0.08264 (9)0.0327 (3)
H320.478 (2)0.1501 (10)−0.0735 (10)0.045 (4)*
O30.64780 (13)0.26946 (5)0.40946 (6)0.0306 (2)
N50.76117 (13)0.49974 (6)0.55516 (6)0.0207 (2)
N60.71477 (13)0.37944 (6)0.37836 (6)0.0201 (2)
C330.75948 (15)0.46950 (7)0.40722 (7)0.0191 (2)
C340.78126 (16)0.50245 (8)0.35079 (8)0.0242 (2)
H340.7675 (19)0.4622 (9)0.2889 (9)0.029 (3)*
C350.82796 (17)0.59192 (9)0.38409 (9)0.0279 (3)
H350.8423 (19)0.6146 (9)0.3469 (9)0.029 (3)*
C360.85515 (17)0.65104 (8)0.47278 (9)0.0281 (3)
H360.891 (2)0.7136 (9)0.4944 (9)0.033 (4)*
C370.83184 (17)0.61908 (8)0.52814 (8)0.0234 (2)
H370.8481 (19)0.6572 (9)0.5903 (9)0.029 (3)*
C380.78320 (15)0.52840 (7)0.49630 (7)0.0195 (2)
C390.71728 (16)0.41640 (7)0.52664 (7)0.0211 (2)
C400.68970 (16)0.34819 (7)0.43423 (7)0.0215 (2)
C410.6911 (2)0.38403 (9)0.58826 (9)0.0291 (3)
H41A0.762 (2)0.3343 (10)0.5804 (10)0.041 (4)*
H41B0.559 (2)0.3606 (10)0.5773 (10)0.048 (4)*
H41C0.732 (2)0.4319 (10)0.6481 (11)0.045 (4)*
C420.69186 (17)0.31401 (8)0.28656 (7)0.0252 (3)
H42A0.7162 (18)0.2580 (9)0.2844 (8)0.027 (3)*
H42B0.788 (2)0.3291 (8)0.2620 (9)0.029 (4)*
C430.50068 (16)0.30338 (7)0.23189 (7)0.0211 (2)
C440.36495 (17)0.35469 (8)0.26581 (8)0.0236 (2)
H440.3899 (18)0.3989 (9)0.3280 (9)0.026 (3)*
C450.19109 (18)0.34284 (8)0.21381 (9)0.0279 (3)
H450.095 (2)0.3820 (9)0.2385 (9)0.037 (4)*
C460.14965 (19)0.27846 (9)0.12749 (8)0.0309 (3)
H460.030 (2)0.2697 (9)0.0929 (9)0.036 (4)*
C470.2840 (2)0.22663 (9)0.09300 (8)0.0328 (3)
H470.257 (2)0.1820 (10)0.0335 (11)0.044 (4)*
C480.45847 (18)0.23918 (8)0.14456 (8)0.0269 (3)
H480.551 (2)0.2010 (9)0.1180 (9)0.030 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0357 (5)0.0181 (4)0.0258 (4)0.0043 (3)0.0032 (4)0.0090 (3)
N10.0185 (5)0.0203 (4)0.0177 (4)0.0015 (4)0.0023 (4)0.0086 (4)
N20.0207 (5)0.0179 (4)0.0193 (5)0.0004 (4)0.0020 (4)0.0095 (4)
C10.0136 (5)0.0195 (5)0.0188 (5)0.0011 (4)0.0005 (4)0.0089 (4)
C20.0182 (6)0.0264 (6)0.0198 (5)0.0021 (4)0.0026 (4)0.0118 (5)
C30.0178 (6)0.0274 (6)0.0178 (5)0.0050 (5)0.0017 (4)0.0052 (5)
C40.0205 (6)0.0183 (5)0.0232 (6)0.0036 (4)−0.0008 (5)0.0056 (5)
C50.0173 (6)0.0200 (5)0.0228 (6)0.0005 (4)−0.0010 (4)0.0105 (5)
C60.0143 (5)0.0204 (5)0.0181 (5)0.0015 (4)0.0002 (4)0.0086 (4)
C70.0137 (5)0.0223 (5)0.0180 (5)0.0013 (4)−0.0003 (4)0.0092 (4)
C80.0181 (6)0.0195 (5)0.0196 (5)0.0022 (4)−0.0009 (4)0.0085 (4)
C90.0254 (7)0.0255 (6)0.0194 (6)0.0038 (5)0.0036 (5)0.0088 (5)
C100.0243 (6)0.0242 (6)0.0245 (6)−0.0013 (5)0.0032 (5)0.0147 (5)
C110.0277 (6)0.0157 (5)0.0209 (5)0.0034 (4)0.0051 (5)0.0084 (4)
C120.0335 (7)0.0221 (6)0.0275 (6)0.0002 (5)0.0078 (5)0.0138 (5)
C130.0472 (9)0.0239 (6)0.0268 (6)0.0059 (5)0.0083 (6)0.0163 (5)
C140.0415 (8)0.0260 (6)0.0249 (6)0.0135 (5)0.0029 (6)0.0128 (5)
C150.0276 (7)0.0318 (6)0.0299 (7)0.0099 (5)0.0062 (5)0.0145 (5)
C160.0276 (7)0.0263 (6)0.0247 (6)0.0063 (5)0.0079 (5)0.0144 (5)
O20.0324 (5)0.0361 (5)0.0211 (4)0.0093 (4)0.0047 (4)0.0165 (4)
N30.0183 (5)0.0192 (4)0.0191 (5)0.0026 (4)0.0053 (4)0.0056 (4)
N40.0203 (5)0.0179 (4)0.0161 (4)0.0033 (4)0.0042 (4)0.0077 (4)
C170.0152 (5)0.0195 (5)0.0158 (5)0.0057 (4)0.0057 (4)0.0081 (4)
C180.0180 (6)0.0204 (5)0.0190 (5)0.0032 (4)0.0044 (4)0.0065 (4)
C190.0177 (6)0.0282 (6)0.0168 (5)0.0067 (5)0.0031 (4)0.0070 (5)
C200.0228 (6)0.0328 (6)0.0197 (5)0.0122 (5)0.0082 (5)0.0153 (5)
C210.0236 (6)0.0233 (5)0.0237 (6)0.0079 (5)0.0102 (5)0.0134 (5)
C220.0157 (5)0.0185 (5)0.0167 (5)0.0040 (4)0.0057 (4)0.0062 (4)
C230.0167 (5)0.0225 (5)0.0174 (5)0.0050 (4)0.0058 (4)0.0062 (4)
C240.0171 (5)0.0245 (5)0.0164 (5)0.0070 (4)0.0051 (4)0.0084 (4)
C250.0223 (6)0.0268 (6)0.0185 (6)0.0013 (5)0.0028 (5)0.0041 (5)
C260.0264 (7)0.0195 (5)0.0226 (6)0.0040 (5)0.0094 (5)0.0103 (5)
C270.0299 (6)0.0192 (5)0.0164 (5)0.0055 (4)0.0054 (5)0.0093 (4)
C280.0272 (6)0.0240 (6)0.0166 (5)0.0055 (5)0.0015 (5)0.0096 (5)
C290.0299 (7)0.0319 (6)0.0176 (5)0.0109 (5)0.0031 (5)0.0104 (5)
C300.0489 (9)0.0250 (6)0.0248 (6)0.0157 (6)0.0091 (6)0.0111 (5)
C310.0591 (10)0.0203 (6)0.0363 (8)0.0065 (6)0.0166 (7)0.0121 (6)
C320.0421 (8)0.0249 (6)0.0330 (7)0.0035 (6)0.0138 (6)0.0139 (5)
O30.0319 (5)0.0207 (4)0.0352 (5)−0.0005 (4)0.0054 (4)0.0114 (4)
N50.0208 (5)0.0230 (5)0.0196 (5)0.0052 (4)0.0055 (4)0.0108 (4)
N60.0197 (5)0.0198 (4)0.0176 (5)0.0036 (4)0.0036 (4)0.0067 (4)
C330.0153 (5)0.0213 (5)0.0206 (5)0.0043 (4)0.0026 (4)0.0105 (4)
C340.0185 (6)0.0355 (6)0.0218 (6)0.0048 (5)0.0022 (5)0.0171 (5)
C350.0216 (6)0.0387 (7)0.0359 (7)0.0055 (5)0.0035 (5)0.0289 (6)
C360.0236 (6)0.0241 (6)0.0399 (7)0.0044 (5)0.0025 (5)0.0197 (6)
C370.0217 (6)0.0217 (5)0.0250 (6)0.0053 (4)0.0034 (5)0.0103 (5)
C380.0165 (5)0.0221 (5)0.0210 (5)0.0051 (4)0.0043 (4)0.0112 (5)
C390.0179 (6)0.0247 (5)0.0228 (6)0.0045 (4)0.0057 (4)0.0128 (5)
C400.0183 (6)0.0219 (5)0.0240 (6)0.0031 (4)0.0034 (4)0.0112 (5)
C410.0318 (7)0.0330 (7)0.0300 (7)0.0032 (6)0.0115 (6)0.0198 (6)
C420.0236 (6)0.0261 (6)0.0191 (6)0.0071 (5)0.0054 (5)0.0051 (5)
C430.0235 (6)0.0213 (5)0.0189 (5)0.0009 (4)0.0040 (4)0.0105 (4)
C440.0241 (6)0.0228 (5)0.0232 (6)0.0014 (5)0.0048 (5)0.0108 (5)
C450.0236 (6)0.0321 (6)0.0366 (7)0.0031 (5)0.0058 (5)0.0240 (6)
C460.0265 (7)0.0415 (7)0.0311 (7)−0.0056 (6)−0.0038 (6)0.0269 (6)
C470.0394 (8)0.0381 (7)0.0183 (6)−0.0062 (6)0.0004 (5)0.0146 (6)
C480.0332 (7)0.0276 (6)0.0206 (6)0.0016 (5)0.0083 (5)0.0116 (5)
Geometric parameters (Å, º) top
O1—C81.2311 (13)C25—H25A0.948 (15)
N1—C71.2944 (14)C25—H25B0.981 (16)
N1—C61.3909 (14)C25—H25C1.000 (16)
N2—C81.3779 (14)C26—C271.5159 (15)
N2—C11.4004 (13)C26—H26A0.983 (15)
N2—C101.4711 (15)C26—H26B0.988 (14)
C1—C21.3986 (15)C27—C281.3874 (17)
C1—C61.4026 (15)C27—C321.3939 (17)
C2—C31.3843 (16)C28—C291.3938 (16)
C2—H20.976 (14)C28—H280.990 (13)
C3—C41.3908 (18)C29—C301.3810 (19)
C3—H31.002 (13)C29—H290.996 (15)
C4—C51.3793 (16)C30—C311.383 (2)
C4—H40.961 (13)C30—H301.008 (14)
C5—C61.4011 (15)C31—C321.3954 (18)
C5—H50.993 (14)C31—H310.970 (16)
C7—C81.4805 (16)C32—H320.994 (16)
C7—C91.4967 (15)O3—C401.2259 (13)
C9—H9A0.990 (18)N5—C391.2892 (14)
C9—H9B0.975 (16)N5—C381.3926 (14)
C9—H9C0.986 (16)N6—C401.3798 (15)
C10—C111.5148 (17)N6—C331.3971 (14)
C10—H10A0.986 (13)N6—C421.4662 (14)
C10—H10B1.012 (13)C33—C381.4048 (15)
C11—C161.3855 (17)C33—C341.4053 (16)
C11—C121.3982 (17)C34—C351.3759 (17)
C12—C131.3850 (18)C34—H340.976 (14)
C12—H120.999 (15)C35—C361.3977 (18)
C13—C141.383 (2)C35—H350.940 (14)
C13—H130.961 (16)C36—C371.3772 (18)
C14—C151.3821 (19)C36—H360.971 (14)
C14—H141.002 (14)C37—C381.4012 (15)
C15—C161.3917 (18)C37—H370.972 (14)
C15—H151.007 (16)C39—C401.4828 (16)
C16—H160.948 (14)C39—C411.4927 (16)
O2—C241.2267 (13)C41—H41A0.990 (15)
N3—C231.2965 (15)C41—H41B0.985 (18)
N3—C221.3942 (14)C41—H41C0.979 (16)
N4—C241.3854 (14)C42—C431.5161 (17)
N4—C171.3958 (14)C42—H42A0.979 (13)
N4—C261.4624 (14)C42—H42B0.982 (15)
C17—C221.4010 (15)C43—C441.3888 (16)
C17—C181.4051 (15)C43—C481.3945 (16)
C18—C191.3817 (16)C44—C451.3884 (17)
C18—H180.986 (14)C44—H440.988 (13)
C19—C201.3949 (17)C45—C461.3825 (18)
C19—H190.953 (13)C45—H451.009 (14)
C20—C211.3798 (17)C46—C471.387 (2)
C20—H200.962 (14)C46—H460.946 (15)
C21—C221.4018 (15)C47—C481.3862 (19)
C21—H210.992 (13)C47—H470.954 (16)
C23—C241.4801 (16)C48—H480.991 (14)
C23—C251.4924 (16)
C7—N1—C6118.37 (10)C23—C25—H25B110.3 (9)
C8—N2—C1121.26 (9)H25A—C25—H25B103.6 (12)
C8—N2—C10118.54 (9)C23—C25—H25C110.7 (9)
C1—N2—C10120.15 (9)H25A—C25—H25C106.7 (13)
C2—C1—N2122.24 (10)H25B—C25—H25C114.0 (13)
C2—C1—C6119.46 (10)N4—C26—C27113.64 (10)
N2—C1—C6118.30 (9)N4—C26—H26A106.3 (8)
C3—C2—C1119.68 (11)C27—C26—H26A111.8 (8)
C3—C2—H2118.8 (8)N4—C26—H26B108.7 (7)
C1—C2—H2121.5 (8)C27—C26—H26B110.3 (7)
C2—C3—C4121.05 (11)H26A—C26—H26B105.7 (11)
C2—C3—H3117.9 (7)C28—C27—C32119.23 (11)
C4—C3—H3121.1 (7)C28—C27—C26121.85 (10)
C5—C4—C3119.69 (10)C32—C27—C26118.89 (11)
C5—C4—H4120.1 (8)C27—C28—C29120.10 (12)
C3—C4—H4120.2 (8)C27—C28—H28119.8 (8)
C4—C5—C6120.25 (11)C29—C28—H28120.1 (8)
C4—C5—H5121.8 (8)C30—C29—C28120.69 (13)
C6—C5—H5118.0 (8)C30—C29—H29121.5 (8)
N1—C6—C5117.89 (10)C28—C29—H29117.8 (8)
N1—C6—C1122.23 (9)C29—C30—C31119.45 (11)
C5—C6—C1119.85 (10)C29—C30—H30120.6 (8)
N1—C7—C8123.90 (10)C31—C30—H30119.9 (8)
N1—C7—C9119.56 (10)C30—C31—C32120.36 (13)
C8—C7—C9116.53 (10)C30—C31—H31118.9 (10)
O1—C8—N2122.39 (10)C32—C31—H31120.8 (10)
O1—C8—C7121.74 (10)C27—C32—C31120.15 (13)
N2—C8—C7115.87 (9)C27—C32—H32119.6 (9)
C7—C9—H9A110.1 (10)C31—C32—H32120.2 (9)
C7—C9—H9B112.4 (9)C39—N5—C38118.69 (9)
H9A—C9—H9B108.1 (13)C40—N6—C33121.90 (9)
C7—C9—H9C110.8 (9)C40—N6—C42117.19 (9)
H9A—C9—H9C106.8 (13)C33—N6—C42120.90 (10)
H9B—C9—H9C108.4 (13)N6—C33—C38117.91 (10)
N2—C10—C11114.25 (10)N6—C33—C34122.53 (10)
N2—C10—H10A108.4 (8)C38—C33—C34119.56 (10)
C11—C10—H10A110.1 (8)C35—C34—C33119.27 (11)
N2—C10—H10B105.3 (8)C35—C34—H34120.3 (8)
C11—C10—H10B109.8 (8)C33—C34—H34120.4 (8)
H10A—C10—H10B108.7 (11)C34—C35—C36121.73 (11)
C16—C11—C12119.09 (11)C34—C35—H35119.9 (8)
C16—C11—C10122.22 (11)C36—C35—H35118.4 (8)
C12—C11—C10118.65 (11)C37—C36—C35119.15 (11)
C13—C12—C11120.27 (13)C37—C36—H36121.2 (8)
C13—C12—H12120.0 (8)C35—C36—H36119.7 (8)
C11—C12—H12119.7 (8)C36—C37—C38120.58 (11)
C14—C13—C12120.42 (12)C36—C37—H37122.6 (8)
C14—C13—H13119.9 (9)C38—C37—H37116.8 (8)
C12—C13—H13119.7 (10)N5—C38—C37118.16 (10)
C15—C14—C13119.52 (12)N5—C38—C33122.14 (10)
C15—C14—H14118.7 (8)C37—C38—C33119.70 (10)
C13—C14—H14121.8 (8)N5—C39—C40123.91 (10)
C14—C15—C16120.50 (13)N5—C39—C41119.75 (10)
C14—C15—H15119.9 (9)C40—C39—C41116.33 (10)
C16—C15—H15119.5 (9)O3—C40—N6122.49 (10)
C11—C16—C15120.20 (12)O3—C40—C39122.08 (11)
C11—C16—H16120.5 (9)N6—C40—C39115.43 (9)
C15—C16—H16119.3 (9)C39—C41—H41A111.6 (9)
C23—N3—C22118.48 (10)C39—C41—H41B110.4 (9)
C24—N4—C17121.54 (9)H41A—C41—H41B105.6 (13)
C24—N4—C26117.97 (9)C39—C41—H41C110.2 (9)
C17—N4—C26120.49 (9)H41A—C41—H41C108.9 (12)
N4—C17—C22118.35 (9)H41B—C41—H41C110.0 (13)
N4—C17—C18122.32 (10)N6—C42—C43113.72 (9)
C22—C17—C18119.33 (10)N6—C42—H42A106.6 (8)
C19—C18—C17120.09 (11)C43—C42—H42A110.5 (8)
C19—C18—H18121.4 (8)N6—C42—H42B110.3 (8)
C17—C18—H18118.5 (8)C43—C42—H42B109.3 (8)
C18—C19—C20120.62 (11)H42A—C42—H42B106.1 (11)
C18—C19—H19117.1 (8)C44—C43—C48118.65 (11)
C20—C19—H19122.2 (8)C44—C43—C42122.39 (10)
C21—C20—C19119.71 (11)C48—C43—C42118.95 (10)
C21—C20—H20122.0 (8)C45—C44—C43120.77 (11)
C19—C20—H20118.3 (8)C45—C44—H44119.1 (8)
C20—C21—C22120.58 (11)C43—C44—H44120.1 (8)
C20—C21—H21119.9 (8)C46—C45—C44120.23 (12)
C22—C21—H21119.5 (8)C46—C45—H45119.7 (8)
N3—C22—C17122.10 (10)C44—C45—H45120.1 (8)
N3—C22—C21118.25 (10)C45—C46—C47119.48 (12)
C17—C22—C21119.64 (10)C45—C46—H46119.7 (9)
N3—C23—C24123.92 (10)C47—C46—H46120.8 (9)
N3—C23—C25119.38 (11)C48—C47—C46120.36 (12)
C24—C23—C25116.70 (10)C48—C47—H47119.4 (10)
O2—C24—N4122.12 (10)C46—C47—H47120.3 (10)
O2—C24—C23122.44 (10)C47—C48—C43120.50 (12)
N4—C24—C23115.43 (9)C47—C48—H48118.3 (8)
C23—C25—H25A111.4 (9)C43—C48—H48121.2 (8)
C8—N2—C1—C2178.23 (10)C26—N4—C24—O24.31 (15)
C10—N2—C1—C2−4.42 (16)C17—N4—C24—C235.08 (14)
C8—N2—C1—C6−1.61 (15)C26—N4—C24—C23−174.92 (9)
C10—N2—C1—C6175.74 (10)N3—C23—C24—O2177.27 (10)
N2—C1—C2—C3179.07 (10)C25—C23—C24—O2−3.28 (15)
C6—C1—C2—C3−1.09 (16)N3—C23—C24—N4−3.50 (15)
C1—C2—C3—C4−0.11 (17)C25—C23—C24—N4175.95 (9)
C2—C3—C4—C51.10 (17)C24—N4—C26—C27−103.32 (11)
C3—C4—C5—C6−0.87 (17)C17—N4—C26—C2776.68 (13)
C7—N1—C6—C5179.64 (10)N4—C26—C27—C2817.37 (15)
C7—N1—C6—C11.57 (15)N4—C26—C27—C32−164.53 (11)
C4—C5—C6—N1−178.44 (10)C32—C27—C28—C29−0.57 (17)
C4—C5—C6—C1−0.32 (16)C26—C27—C28—C29177.52 (10)
C2—C1—C6—N1179.34 (10)C27—C28—C29—C30−0.45 (17)
N2—C1—C6—N1−0.82 (15)C28—C29—C30—C310.80 (19)
C2—C1—C6—C51.31 (16)C29—C30—C31—C32−0.1 (2)
N2—C1—C6—C5−178.85 (9)C28—C27—C32—C311.25 (19)
C6—N1—C7—C80.03 (16)C26—C27—C32—C31−176.91 (12)
C6—N1—C7—C9−178.35 (10)C30—C31—C32—C27−0.9 (2)
C1—N2—C8—O1−177.94 (10)C40—N6—C33—C381.53 (16)
C10—N2—C8—O14.66 (16)C42—N6—C33—C38−178.70 (10)
C1—N2—C8—C73.00 (15)C40—N6—C33—C34−178.52 (10)
C10—N2—C8—C7−174.40 (9)C42—N6—C33—C341.26 (16)
N1—C7—C8—O1178.65 (10)N6—C33—C34—C35−179.09 (10)
C9—C7—C8—O1−2.92 (16)C38—C33—C34—C350.86 (17)
N1—C7—C8—N2−2.28 (16)C33—C34—C35—C360.26 (18)
C9—C7—C8—N2176.14 (10)C34—C35—C36—C37−1.00 (18)
C8—N2—C10—C11−106.81 (11)C35—C36—C37—C380.59 (18)
C1—N2—C10—C1175.76 (13)C39—N5—C38—C37−179.68 (10)
N2—C10—C11—C1622.47 (15)C39—N5—C38—C33−0.12 (16)
N2—C10—C11—C12−159.76 (10)C36—C37—C38—N5−179.91 (10)
C16—C11—C12—C13−0.50 (17)C36—C37—C38—C330.52 (17)
C10—C11—C12—C13−178.35 (11)N6—C33—C38—N5−0.85 (16)
C11—C12—C13—C14−0.20 (18)C34—C33—C38—N5179.20 (10)
C12—C13—C14—C150.80 (18)N6—C33—C38—C37178.71 (10)
C13—C14—C15—C16−0.69 (18)C34—C33—C38—C37−1.25 (16)
C12—C11—C16—C150.61 (17)C38—N5—C39—C400.46 (16)
C10—C11—C16—C15178.37 (11)C38—N5—C39—C41−179.43 (10)
C14—C15—C16—C11−0.01 (18)C33—N6—C40—O3178.91 (10)
C24—N4—C17—C22−3.62 (15)C42—N6—C40—O3−0.87 (16)
C26—N4—C17—C22176.38 (9)C33—N6—C40—C39−1.20 (15)
C24—N4—C17—C18176.43 (9)C42—N6—C40—C39179.02 (10)
C26—N4—C17—C18−3.57 (15)N5—C39—C40—O3−179.93 (11)
N4—C17—C18—C19179.35 (9)C41—C39—C40—O3−0.04 (16)
C22—C17—C18—C19−0.61 (15)N5—C39—C40—N60.18 (16)
C17—C18—C19—C20−0.74 (16)C41—C39—C40—N6−179.92 (10)
C18—C19—C20—C211.39 (16)C40—N6—C42—C4397.49 (12)
C19—C20—C21—C22−0.67 (16)C33—N6—C42—C43−82.29 (13)
C23—N3—C22—C171.47 (15)N6—C42—C43—C443.16 (17)
C23—N3—C22—C21−179.74 (9)N6—C42—C43—C48−176.14 (11)
N4—C17—C22—N30.13 (15)C48—C43—C44—C45−0.44 (17)
C18—C17—C22—N3−179.91 (9)C42—C43—C44—C45−179.74 (11)
N4—C17—C22—C21−178.65 (9)C43—C44—C45—C461.09 (18)
C18—C17—C22—C211.31 (15)C44—C45—C46—C47−0.87 (18)
C20—C21—C22—N3−179.50 (10)C45—C46—C47—C480.01 (19)
C20—C21—C22—C17−0.68 (16)C46—C47—C48—C430.64 (19)
C22—N3—C23—C240.29 (15)C44—C43—C48—C47−0.42 (18)
C22—N3—C23—C25−179.15 (10)C42—C43—C48—C47178.91 (12)
C17—N4—C24—O2−175.69 (9)
Hydrogen-bond geometry (Å, º) top
Cg2, Cg3, Cg6, Cg7 and Cg11 are the centroids of the C1–C6, C11–C16, C17–C22, C27–C32 and C43–C48 benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg7i1.002 (13)2.867 (13)3.6440 (13)134.8 (11)
C9—H9C···Cg2ii0.986 (16)2.746 (13)3.4470 (14)128.4 (13)
C12—H12···O30.999 (15)2.429 (14)3.2448 (16)138.5 (10)
C13—H13···Cg110.961 (16)2.718 (19)3.5058 (17)139.8 (13)
C16—H16···N1ii0.948 (14)2.457 (15)3.3430 (16)155.5 (11)
C19—H19···O1iii0.953 (13)2.553 (14)3.5016 (14)174.1 (11)
C25—H25C···Cg6iv1.000 (16)2.835 (15)3.4591 (14)121.3 (12)
C28—H28···N3iv0.990 (13)2.538 (14)3.4672 (16)156.3 (10)
C30—H30···Cg3i1.008 (14)2.636 (16)3.5668 (15)153.9 (12)
C34—H34···O20.976 (14)2.575 (14)3.4126 (15)144.0 (11)
C44—H44···N5v0.988 (13)2.490 (13)3.3333 (15)143.1 (10)
Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y, −z+1; (iii) x, y, z−1; (iv) −x+2, −y+1, −z; (v) −x+1, −y+1, −z+1.
 

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

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ISSN: 2414-3146
Volume 3| Part 3| March 2018| x180390
https://doi.org/10.1107/S2414314618003905
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